(5S)-4-(2,2-Dimethyl-prop-yl)-5-isopropyl-1,3,4-oxadiazinan-2-one.

The title compound, C(11)H(22)N(2)O(2), has one chiral center and packs in the monoclinic space group P2(1). The asymmetric unit has five crystallographically independent mol-ecules, four of which engage in inter-molecular N-H⋯O hydrogen bonding.

Related literature

For related structures and background, see: Addison et al. (2008 ▶); Anderson et al. (2006 ▶); Burgeson et al. (2004 ▶); Casper et al. (2002 ▶); Rodrigues et al. (2006 ▶); Szczepura et al. (2004 ▶); Trepanier et al. (1968 ▶). The synthesis of the title compound is described by Casper et al. (2004 ▶). For literature related to crystallographic analysis, see: Allen (2002 ▶); Bernstein et al. (1995 ▶); Boeyens (1978 ▶); Bruno et al. (2004 ▶); Cremer & Pople (1975 ▶); Etter et al. (1990 ▶); Macrae et al. (2008 ▶); Spek (2009 ▶).

Experimental

Crystal data

C11H22N2O2

M = 214.3

Monoclinic,

a = 17.0330 (18) Å

b = 11.2270 (12) Å

c = 17.404 (2) Å

β = 100.073 (2)°

V = 3276.9 (6) Å3

Z = 10

Mo Kα radiation

μ = 0.08 mm−1

T = 193 K

0.6 × 0.32 × 0.27 mm

Data collection

Bruker P4/R4/SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 1999 ▶) T min = 0.812, T max = 0.943

16431 measured reflections

7042 independent reflections

4526 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.144

S = 1.03

7042 reflections

723 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), publCIF (Westrip, 2010) ▶ and Mercury (Macrae et al., 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048798/zl2318sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048798/zl2318Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Enhanced figure: interactive version of Fig. 4

C11H22N2O2	F(000) = 1180
Mr = 214.3	Dx = 1.086 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 6729 reflections
a = 17.0330 (18) Å	θ = 2.4–22.8°
b = 11.2270 (12) Å	µ = 0.08 mm−1
c = 17.404 (2) Å	T = 193 K
β = 100.073 (2)°	Prism, colourless
V = 3276.9 (6) Å3	0.6 × 0.32 × 0.27 mm
Z = 10

Bruker P4/R4/SMART 1000 CCD diffractometer	4526 reflections with I > 2σ(I)
ω scans	Rint = 0.044
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 1999)	θmax = 26.4°, θmin = 1.2°
Tmin = 0.812, Tmax = 0.943	h = −21→21
16431 measured reflections	k = −11→14
7042 independent reflections	l = −19→21

Refinement on F2	1 restraint
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.052	w = 1/[σ2(Fo2) + (0.0763P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.144	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.27 e Å−3
7042 reflections	Δρmin = −0.17 e Å−3
723 parameters

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.4885 (2)	0.4683 (3)	−0.06758 (17)	0.0693 (9)
C2	0.4247 (3)	0.4157 (5)	−0.0465 (3)	0.0679 (13)
N3	0.4016 (2)	0.4554 (4)	0.0188 (3)	0.0625 (10)
N4	0.44061 (17)	0.5387 (3)	0.07359 (18)	0.0427 (7)
C5	0.5244 (2)	0.5438 (3)	0.0642 (2)	0.0418 (9)
H5	0.5489	0.6146	0.0941	0.05*
C6	0.5273 (3)	0.5655 (4)	−0.0204 (2)	0.0585 (11)
H6A	0.5	0.6414	−0.0373	0.07*
H6B	0.5834	0.572	−0.0278	0.07*
C7	0.5696 (2)	0.4339 (4)	0.0995 (2)	0.0472 (9)
H7	0.5419	0.3622	0.0737	0.057*
C8	0.6560 (2)	0.4309 (5)	0.0861 (3)	0.0677 (13)
H8A	0.6821	0.3586	0.1096	0.102*
H8B	0.6845	0.5011	0.1102	0.102*
H8C	0.6568	0.4311	0.0299	0.102*
C9	0.5678 (3)	0.4252 (5)	0.1864 (3)	0.0690 (13)
H9A	0.597	0.3539	0.2078	0.103*
H9B	0.5124	0.4199	0.1945	0.103*
H9C	0.5929	0.4961	0.213	0.103*
C10	0.3986 (2)	0.6556 (3)	0.0666 (2)	0.0505 (10)
H10A	0.3527	0.6517	0.023	0.061*
H10B	0.4354	0.7179	0.0539	0.061*
C11	0.3688 (2)	0.6901 (3)	0.1414 (2)	0.0443 (9)
C12	0.3260 (3)	0.8094 (4)	0.1264 (3)	0.0634 (12)
H12A	0.2807	0.8009	0.0834	0.095*
H12B	0.3631	0.8691	0.1124	0.095*
H12C	0.3067	0.835	0.1736	0.095*
C13	0.3113 (3)	0.5967 (4)	0.1610 (3)	0.0792 (15)
H13A	0.2668	0.5885	0.1174	0.119*
H13B	0.291	0.6209	0.208	0.119*
H13C	0.3391	0.5202	0.1705	0.119*
C14	0.4384 (3)	0.7049 (5)	0.2076 (3)	0.0706 (13)
H14A	0.4751	0.7651	0.1934	0.106*
H14B	0.4665	0.6288	0.2175	0.106*
H14C	0.4189	0.7304	0.2547	0.106*
O15	0.3927 (2)	0.3348 (4)	−0.0854 (3)	0.1060 (15)
H3	0.365 (3)	0.416 (5)	0.035 (3)	0.073 (16)*
O21	0.60240 (16)	0.0228 (3)	0.35395 (17)	0.0629 (8)
C22	0.6241 (2)	0.0932 (4)	0.4166 (2)	0.0528 (11)
N23	0.56820 (19)	0.1295 (3)	0.4561 (2)	0.0483 (9)
N24	0.48479 (16)	0.1070 (3)	0.43763 (17)	0.0439 (7)
C25	0.4650 (2)	0.0769 (4)	0.3543 (2)	0.0477 (10)
H25	0.4099	0.0429	0.3446	0.057*
C26	0.5212 (2)	−0.0197 (4)	0.3368 (3)	0.0602 (11)
H26A	0.5153	−0.091	0.3688	0.072*
H26B	0.5077	−0.0425	0.2811	0.072*
C27	0.4643 (2)	0.1884 (4)	0.3030 (2)	0.0557 (10)
H27	0.519	0.2241	0.3128	0.067*
C28	0.4435 (3)	0.1552 (6)	0.2171 (3)	0.0893 (17)
H28A	0.4816	0.0958	0.2047	0.134*
H28B	0.4461	0.2264	0.185	0.134*
H28C	0.3895	0.122	0.2061	0.134*
C29	0.4062 (3)	0.2798 (5)	0.3235 (3)	0.0782 (14)
H29A	0.4067	0.3501	0.2902	0.117*
H29B	0.4217	0.3029	0.3783	0.117*
H29C	0.3524	0.2456	0.3152	0.117*
C30	0.4607 (3)	0.0152 (4)	0.4906 (3)	0.0594 (11)
H30A	0.5086	−0.0121	0.527	0.071*
H30B	0.4383	−0.0543	0.4592	0.071*
C31	0.3996 (2)	0.0603 (4)	0.5375 (2)	0.0539 (11)
C32	0.3795 (3)	−0.0402 (6)	0.5887 (3)	0.0896 (17)
H32A	0.4276	−0.0641	0.625	0.134*
H32B	0.359	−0.1083	0.556	0.134*
H32C	0.3388	−0.0133	0.6183	0.134*
C33	0.4337 (4)	0.1663 (6)	0.5866 (3)	0.115 (3)
H33A	0.4822	0.142	0.6221	0.172*
H33B	0.3943	0.1952	0.6171	0.172*
H33C	0.4465	0.2301	0.5524	0.172*
C34	0.3249 (3)	0.0960 (5)	0.4830 (3)	0.0831 (16)
H34A	0.3368	0.1618	0.4499	0.125*
H34B	0.2846	0.1215	0.5134	0.125*
H34C	0.3046	0.0279	0.4502	0.125*
O35	0.69335 (16)	0.1255 (4)	0.43234 (17)	0.0761 (10)
H23	0.584 (2)	0.169 (4)	0.492 (3)	0.051 (13)*
O41	0.26808 (14)	0.8230 (3)	0.31233 (16)	0.0557 (7)
C42	0.2958 (2)	0.7617 (4)	0.3774 (2)	0.0442 (9)
N43	0.24610 (18)	0.6941 (3)	0.4097 (2)	0.0474 (8)
N44	0.16241 (17)	0.6874 (3)	0.38521 (18)	0.0481 (8)
C45	0.1355 (2)	0.7981 (4)	0.3434 (2)	0.0526 (11)
H45	0.0787	0.7861	0.3181	0.063*
C46	0.1835 (2)	0.8159 (5)	0.2790 (2)	0.0596 (11)
H46A	0.1741	0.7486	0.2418	0.071*
H46B	0.1664	0.8902	0.2502	0.071*
C47	0.1371 (2)	0.9001 (4)	0.4006 (3)	0.0637 (12)
H47	0.193	0.9072	0.4297	0.076*
C48	0.1156 (5)	1.0160 (7)	0.3609 (5)	0.134 (3)
H48A	0.1172	1.079	0.4001	0.201*
H48B	0.0617	1.0109	0.3301	0.201*
H48C	0.1536	1.0345	0.3264	0.201*
C49	0.0835 (4)	0.8758 (7)	0.4601 (4)	0.117 (2)
H49A	0.0982	0.7995	0.486	0.176*
H49B	0.0278	0.8726	0.4335	0.176*
H49C	0.0898	0.9397	0.499	0.176*
C50	0.1397 (3)	0.5776 (5)	0.3403 (3)	0.0758 (14)
H50A	0.1791	0.5632	0.3057	0.091*
H50B	0.0873	0.5906	0.3066	0.091*
C51	0.1346 (3)	0.4674 (5)	0.3887 (3)	0.0726 (14)
C52A	0.2148 (10)	0.4158 (14)	0.4062 (10)	0.099 (5)	0.5
H52A	0.2136	0.3437	0.4376	0.148*	0.5
H52B	0.2515	0.4738	0.4352	0.148*	0.5
H52C	0.2328	0.3956	0.3573	0.148*	0.5
C53A	0.0741 (8)	0.3832 (14)	0.3425 (10)	0.099 (5)	0.5
H53A	0.0701	0.3109	0.3731	0.149*	0.5
H53B	0.0914	0.362	0.2934	0.149*	0.5
H53C	0.022	0.4224	0.3312	0.149*	0.5
C54A	0.1074 (11)	0.5004 (16)	0.4667 (10)	0.116 (6)	0.5
H54A	0.1044	0.4281	0.4975	0.175*	0.5
H54B	0.0547	0.5382	0.4556	0.175*	0.5
H54C	0.1458	0.5558	0.4961	0.175*	0.5
C52B	0.2081 (13)	0.4386 (14)	0.4517 (9)	0.110 (6)	0.5
H52D	0.2549	0.427	0.4268	0.164*	0.5
H52E	0.198	0.3657	0.4794	0.164*	0.5
H52F	0.218	0.5048	0.4889	0.164*	0.5
C53B	0.1269 (12)	0.3535 (13)	0.3335 (9)	0.110 (5)	0.5
H53D	0.1754	0.345	0.311	0.164*	0.5
H53E	0.0808	0.3631	0.2914	0.164*	0.5
H53F	0.1195	0.2823	0.364	0.164*	0.5
C54B	0.0622 (11)	0.4802 (16)	0.4233 (13)	0.130 (7)	0.5
H54D	0.0563	0.4103	0.4556	0.196*	0.5
H54E	0.0155	0.4868	0.3817	0.196*	0.5
H54F	0.0665	0.552	0.4558	0.196*	0.5
O55	0.36702 (14)	0.7706 (3)	0.40520 (15)	0.0533 (7)
H43	0.262 (2)	0.673 (3)	0.459 (2)	0.041 (10)*
O61	−0.06692 (15)	0.3012 (3)	−0.09221 (17)	0.0681 (9)
C62	−0.0031 (2)	0.3696 (4)	−0.0965 (3)	0.0547 (11)
N63	0.0563 (2)	0.3695 (3)	−0.03533 (19)	0.0466 (8)
N64	0.05885 (16)	0.3060 (3)	0.03561 (18)	0.0431 (7)
C65	−0.0238 (2)	0.2907 (4)	0.0483 (3)	0.0546 (11)
H65	−0.0228	0.234	0.0928	0.066*
C66	−0.0709 (2)	0.2334 (5)	−0.0230 (3)	0.0670 (14)
H66A	−0.05	0.1522	−0.0289	0.08*
H66B	−0.1273	0.2259	−0.0165	0.08*
C67	−0.0578 (2)	0.4086 (4)	0.0716 (3)	0.0648 (13)
H67	−0.0659	0.4619	0.0248	0.078*
C68	−0.1395 (3)	0.3876 (6)	0.0954 (4)	0.118 (3)
H68A	−0.1747	0.3467	0.053	0.177*
H68B	−0.163	0.4643	0.1057	0.177*
H68C	−0.1327	0.3383	0.1426	0.177*
C69	−0.0022 (4)	0.4701 (7)	0.1355 (4)	0.112 (2)
H69A	−0.0263	0.545	0.1487	0.168*
H69B	0.0483	0.4869	0.118	0.168*
H69C	0.0077	0.4187	0.1817	0.168*
C70	0.1029 (2)	0.1934 (4)	0.0357 (2)	0.0482 (9)
H70A	0.1085	0.1742	−0.0186	0.058*
H70B	0.0713	0.129	0.0543	0.058*
C71	0.1850 (2)	0.1955 (4)	0.0860 (3)	0.0574 (11)
C72	0.2217 (3)	0.0725 (4)	0.0846 (4)	0.0850 (17)
H72A	0.1869	0.0136	0.1031	0.128*
H72B	0.274	0.0717	0.1186	0.128*
H72C	0.228	0.0529	0.0311	0.128*
C73	0.2369 (3)	0.2847 (6)	0.0590 (6)	0.135 (3)
H73A	0.2433	0.2662	0.0054	0.203*
H73B	0.2891	0.2838	0.0931	0.203*
H73C	0.2129	0.3639	0.0604	0.203*
C74	0.1731 (5)	0.2199 (8)	0.1695 (4)	0.151 (4)
H74A	0.1381	0.1589	0.1855	0.227*
H74B	0.1488	0.2985	0.1722	0.227*
H74C	0.2248	0.2179	0.2045	0.227*
O75	−0.00226 (17)	0.4282 (4)	−0.15440 (18)	0.0753 (10)
H63	0.092 (2)	0.422 (4)	−0.030 (2)	0.039 (11)*
O81	0.26791 (18)	0.5980 (3)	0.87572 (16)	0.0671 (8)
C82	0.2004 (3)	0.5404 (4)	0.8848 (2)	0.0540 (10)
N83	0.1615 (2)	0.4771 (3)	0.82481 (18)	0.0471 (8)
N84	0.18487 (17)	0.4653 (3)	0.75098 (17)	0.0410 (7)
C85	0.2253 (2)	0.5750 (3)	0.7346 (2)	0.0445 (9)
H85	0.248	0.5615	0.6862	0.053*
C86	0.2943 (3)	0.5952 (4)	0.8008 (3)	0.0614 (12)
H86A	0.3339	0.5305	0.801	0.074*
H86B	0.3207	0.6715	0.7926	0.074*
C87	0.1666 (3)	0.6781 (4)	0.7187 (3)	0.0571 (11)
H87	0.144	0.6927	0.7671	0.068*
C88	0.2050 (4)	0.7922 (5)	0.6981 (3)	0.0865 (16)
H88A	0.1646	0.8551	0.6882	0.13*
H88B	0.2285	0.7798	0.6512	0.13*
H88C	0.2468	0.8159	0.7415	0.13*
C89	0.0988 (3)	0.6471 (5)	0.6541 (4)	0.111 (2)
H89A	0.0741	0.5724	0.6668	0.167*
H89B	0.1191	0.6376	0.6051	0.167*
H89C	0.059	0.711	0.6484	0.167*
C90	0.2337 (2)	0.3574 (4)	0.7488 (3)	0.0539 (10)
H90A	0.2631	0.3415	0.8021	0.065*
H90B	0.2736	0.3729	0.7149	0.065*
C91	0.1870 (3)	0.2476 (4)	0.7195 (3)	0.0619 (12)
C92	0.2443 (4)	0.1445 (5)	0.7213 (5)	0.114 (2)
H92A	0.2651	0.1229	0.7757	0.172*
H92B	0.2886	0.1676	0.6953	0.172*
H92C	0.2164	0.076	0.6942	0.172*
C93	0.1213 (5)	0.2203 (5)	0.7643 (5)	0.126 (3)
H93A	0.1442	0.2063	0.8192	0.189*
H93B	0.0925	0.1489	0.7425	0.189*
H93C	0.0843	0.2878	0.7603	0.189*
C94	0.1492 (5)	0.2668 (7)	0.6349 (4)	0.129 (3)
H94A	0.1189	0.1956	0.615	0.193*
H94B	0.1909	0.2818	0.6038	0.193*
H94C	0.1131	0.3355	0.631	0.193*
O95	0.1774 (2)	0.5505 (3)	0.94701 (17)	0.0708 (9)
H83	0.111 (3)	0.459 (4)	0.828 (2)	0.057 (12)*

	U11	U22	U33	U12	U13	U23
O1	0.094 (2)	0.066 (2)	0.0474 (19)	0.018 (2)	0.0094 (16)	−0.0103 (16)
C2	0.062 (3)	0.061 (3)	0.071 (3)	0.019 (3)	−0.016 (3)	−0.021 (3)
N3	0.0434 (19)	0.051 (2)	0.091 (3)	0.0002 (18)	0.008 (2)	−0.019 (2)
N4	0.0435 (17)	0.0341 (17)	0.0500 (19)	0.0035 (14)	0.0072 (14)	−0.0024 (14)
C5	0.046 (2)	0.039 (2)	0.042 (2)	−0.0077 (17)	0.0120 (16)	−0.0003 (16)
C6	0.072 (3)	0.057 (3)	0.051 (3)	0.009 (2)	0.023 (2)	0.007 (2)
C7	0.041 (2)	0.052 (3)	0.048 (2)	0.0035 (18)	0.0075 (17)	0.0005 (18)
C8	0.044 (2)	0.096 (4)	0.065 (3)	0.011 (2)	0.016 (2)	−0.002 (3)
C9	0.073 (3)	0.083 (3)	0.056 (3)	0.028 (3)	0.024 (2)	0.024 (2)
C10	0.061 (2)	0.043 (2)	0.045 (2)	0.0172 (19)	0.0050 (19)	0.0033 (17)
C11	0.055 (2)	0.035 (2)	0.045 (2)	0.0106 (18)	0.0135 (17)	0.0044 (17)
C12	0.085 (3)	0.047 (2)	0.063 (3)	0.024 (2)	0.025 (2)	0.005 (2)
C13	0.085 (3)	0.051 (3)	0.115 (4)	0.007 (3)	0.054 (3)	0.008 (3)
C14	0.090 (3)	0.073 (3)	0.047 (3)	0.021 (3)	0.004 (2)	−0.013 (2)
O15	0.095 (3)	0.083 (3)	0.121 (3)	0.017 (2)	−0.034 (2)	−0.060 (2)
O21	0.0514 (16)	0.087 (2)	0.0508 (18)	0.0006 (16)	0.0119 (13)	−0.0258 (16)
C22	0.045 (2)	0.077 (3)	0.037 (2)	0.001 (2)	0.0083 (17)	−0.013 (2)
N23	0.0409 (18)	0.066 (2)	0.037 (2)	−0.0028 (17)	0.0055 (15)	−0.0118 (17)
N24	0.0366 (16)	0.054 (2)	0.0412 (18)	−0.0047 (14)	0.0076 (13)	−0.0021 (15)
C25	0.039 (2)	0.056 (3)	0.046 (2)	−0.0114 (18)	0.0031 (16)	−0.0085 (18)
C26	0.057 (2)	0.067 (3)	0.057 (3)	−0.011 (2)	0.011 (2)	−0.018 (2)
C27	0.050 (2)	0.074 (3)	0.040 (2)	−0.004 (2)	0.0008 (17)	0.000 (2)
C28	0.094 (4)	0.119 (5)	0.048 (3)	0.002 (4)	−0.007 (3)	−0.007 (3)
C29	0.081 (3)	0.081 (4)	0.072 (3)	0.015 (3)	0.012 (3)	0.017 (3)
C30	0.060 (2)	0.057 (3)	0.065 (3)	0.006 (2)	0.020 (2)	0.011 (2)
C31	0.060 (3)	0.054 (3)	0.052 (2)	−0.013 (2)	0.021 (2)	−0.0082 (19)
C32	0.108 (4)	0.097 (4)	0.075 (4)	−0.007 (4)	0.049 (3)	0.012 (3)
C33	0.141 (5)	0.138 (6)	0.080 (4)	−0.077 (5)	0.061 (4)	−0.058 (4)
C34	0.056 (3)	0.086 (4)	0.115 (4)	0.002 (3)	0.036 (3)	0.010 (3)
O35	0.0401 (16)	0.135 (3)	0.0543 (19)	−0.0083 (18)	0.0124 (13)	−0.0325 (19)
O41	0.0426 (14)	0.078 (2)	0.0464 (16)	0.0020 (14)	0.0070 (12)	0.0207 (14)
C42	0.038 (2)	0.053 (2)	0.042 (2)	0.0055 (19)	0.0077 (17)	0.0018 (18)
N43	0.0388 (17)	0.061 (2)	0.041 (2)	0.0029 (16)	0.0049 (14)	0.0135 (17)
N44	0.0369 (16)	0.057 (2)	0.047 (2)	−0.0061 (16)	−0.0007 (14)	0.0031 (16)
C45	0.035 (2)	0.064 (3)	0.056 (3)	0.0010 (19)	0.0001 (17)	0.008 (2)
C46	0.049 (2)	0.075 (3)	0.050 (3)	0.004 (2)	−0.0031 (19)	0.018 (2)
C47	0.043 (2)	0.062 (3)	0.086 (4)	0.009 (2)	0.009 (2)	0.009 (3)
C48	0.167 (7)	0.094 (5)	0.138 (7)	0.065 (5)	0.018 (5)	0.020 (5)
C49	0.125 (5)	0.121 (6)	0.124 (6)	0.006 (4)	0.071 (5)	−0.018 (4)
C50	0.088 (4)	0.079 (4)	0.055 (3)	−0.029 (3)	−0.003 (2)	−0.001 (3)
C51	0.089 (4)	0.065 (3)	0.059 (3)	−0.018 (3)	0.003 (3)	−0.002 (3)
C52A	0.108 (10)	0.055 (7)	0.118 (14)	0.012 (7)	−0.021 (11)	−0.014 (9)
C53A	0.088 (9)	0.077 (11)	0.121 (12)	−0.021 (8)	−0.014 (9)	0.000 (8)
C54A	0.135 (15)	0.111 (12)	0.113 (13)	−0.048 (11)	0.048 (10)	0.036 (10)
C52B	0.179 (16)	0.056 (9)	0.082 (11)	−0.013 (9)	−0.010 (12)	0.012 (7)
C53B	0.176 (17)	0.058 (8)	0.084 (9)	−0.016 (11)	−0.005 (12)	−0.015 (6)
C54B	0.124 (14)	0.102 (11)	0.18 (2)	−0.054 (11)	0.081 (13)	−0.015 (13)
O55	0.0359 (14)	0.0705 (19)	0.0539 (17)	0.0041 (13)	0.0090 (12)	0.0103 (14)
O61	0.0407 (15)	0.103 (3)	0.0592 (19)	−0.0076 (16)	0.0054 (13)	0.0175 (18)
C62	0.035 (2)	0.079 (3)	0.052 (3)	0.012 (2)	0.0137 (19)	0.015 (2)
N63	0.0367 (17)	0.058 (2)	0.047 (2)	0.0010 (18)	0.0126 (15)	0.0105 (16)
N64	0.0358 (16)	0.0461 (19)	0.0489 (19)	0.0097 (14)	0.0116 (13)	0.0123 (14)
C65	0.040 (2)	0.067 (3)	0.060 (3)	0.012 (2)	0.0177 (19)	0.029 (2)
C66	0.037 (2)	0.083 (4)	0.081 (3)	−0.004 (2)	0.012 (2)	0.022 (3)
C67	0.056 (2)	0.083 (3)	0.063 (3)	0.034 (2)	0.031 (2)	0.032 (3)
C68	0.088 (4)	0.130 (6)	0.159 (6)	0.046 (4)	0.083 (4)	0.063 (5)
C69	0.128 (5)	0.125 (5)	0.082 (4)	0.071 (5)	0.016 (4)	−0.016 (4)
C70	0.0370 (19)	0.040 (2)	0.067 (3)	0.0046 (18)	0.0091 (18)	−0.0033 (19)
C71	0.043 (2)	0.047 (2)	0.076 (3)	0.014 (2)	−0.0071 (19)	−0.004 (2)
C72	0.052 (3)	0.056 (3)	0.138 (5)	0.021 (2)	−0.011 (3)	−0.008 (3)
C73	0.045 (3)	0.078 (4)	0.267 (10)	−0.013 (3)	−0.019 (4)	0.047 (5)
C74	0.173 (7)	0.174 (8)	0.083 (5)	0.106 (7)	−0.041 (5)	−0.021 (5)
O75	0.0564 (17)	0.121 (3)	0.0505 (19)	0.0068 (18)	0.0150 (14)	0.0320 (19)
O81	0.081 (2)	0.073 (2)	0.0465 (17)	−0.0336 (17)	0.0100 (15)	−0.0064 (15)
C82	0.075 (3)	0.046 (2)	0.041 (2)	−0.014 (2)	0.013 (2)	0.0003 (19)
N83	0.053 (2)	0.050 (2)	0.0419 (19)	−0.0141 (17)	0.0191 (15)	−0.0075 (15)
N84	0.0451 (16)	0.0406 (17)	0.0418 (18)	−0.0061 (15)	0.0201 (13)	−0.0026 (14)
C85	0.050 (2)	0.044 (2)	0.044 (2)	−0.0114 (18)	0.0204 (18)	−0.0033 (17)
C86	0.059 (3)	0.067 (3)	0.060 (3)	−0.026 (2)	0.015 (2)	0.001 (2)
C87	0.081 (3)	0.043 (2)	0.054 (3)	−0.001 (2)	0.030 (2)	0.0006 (19)
C88	0.118 (4)	0.050 (3)	0.086 (4)	−0.022 (3)	0.004 (3)	0.008 (3)
C89	0.077 (4)	0.062 (4)	0.177 (7)	0.008 (3)	−0.027 (4)	0.022 (4)
C90	0.050 (2)	0.056 (3)	0.058 (3)	0.003 (2)	0.0167 (19)	0.004 (2)
C91	0.080 (3)	0.048 (3)	0.064 (3)	0.001 (2)	0.029 (2)	0.001 (2)
C92	0.151 (6)	0.057 (4)	0.150 (6)	0.030 (4)	0.067 (5)	0.006 (4)
C93	0.162 (6)	0.064 (4)	0.178 (7)	−0.050 (4)	0.102 (6)	−0.033 (4)
C94	0.201 (8)	0.088 (5)	0.082 (5)	−0.001 (5)	−0.017 (5)	−0.028 (4)
O95	0.107 (2)	0.068 (2)	0.0438 (18)	−0.0209 (19)	0.0316 (16)	−0.0081 (15)

O1—C2	1.342 (6)	C51—C52A	1.465 (16)
O1—C6	1.453 (6)	C51—C54B	1.472 (17)
C2—O15	1.205 (5)	C51—C53A	1.521 (15)
C2—N3	1.342 (6)	C51—C52B	1.548 (18)
N3—N4	1.415 (5)	C51—C54A	1.554 (18)
N3—H3	0.85 (5)	C51—C53B	1.591 (15)
N4—C5	1.466 (4)	C52A—H52A	0.98
N4—C10	1.489 (5)	C52A—H52B	0.98
C5—C6	1.502 (5)	C52A—H52C	0.98
C5—C7	1.525 (5)	C53A—H53A	0.98
C5—H5	1	C53A—H53B	0.98
C6—H6A	0.99	C53A—H53C	0.98
C6—H6B	0.99	C54A—H54A	0.98
C7—C9	1.522 (6)	C54A—H54B	0.98
C7—C8	1.530 (5)	C54A—H54C	0.98
C7—H7	1	C52B—H52D	0.98
C8—H8A	0.98	C52B—H52E	0.98
C8—H8B	0.98	C52B—H52F	0.98
C8—H8C	0.98	C53B—H53D	0.98
C9—H9A	0.98	C53B—H53E	0.98
C9—H9B	0.98	C53B—H53F	0.98
C9—H9C	0.98	C54B—H54D	0.98
C10—C11	1.529 (5)	C54B—H54E	0.98
C10—H10A	0.99	C54B—H54F	0.98
C10—H10B	0.99	O61—C62	1.343 (5)
C11—C14	1.511 (6)	O61—C66	1.436 (5)
C11—C13	1.513 (6)	C62—O75	1.206 (5)
C11—C12	1.526 (5)	C62—N63	1.335 (5)
C12—H12A	0.98	N63—N64	1.420 (4)
C12—H12B	0.98	N63—H63	0.84 (4)
C12—H12C	0.98	N64—C70	1.470 (5)
C13—H13A	0.98	N64—C65	1.473 (4)
C13—H13B	0.98	C65—C66	1.501 (7)
C13—H13C	0.98	C65—C67	1.527 (6)
C14—H14A	0.98	C65—H65	1
C14—H14B	0.98	C66—H66A	0.99
C14—H14C	0.98	C66—H66B	0.99
O21—C22	1.345 (5)	C67—C69	1.498 (8)
O21—C26	1.444 (5)	C67—C68	1.538 (6)
C22—O35	1.219 (5)	C67—H67	1
C22—N23	1.331 (5)	C68—H68A	0.98
N23—N24	1.423 (4)	C68—H68B	0.98
N23—H23	0.78 (4)	C68—H68C	0.98
N24—C25	1.469 (5)	C69—H69A	0.98
N24—C30	1.487 (5)	C69—H69B	0.98
C25—C26	1.511 (6)	C69—H69C	0.98
C25—C27	1.537 (6)	C70—C71	1.514 (5)
C25—H25	1	C70—H70A	0.99
C26—H26A	0.99	C70—H70B	0.99
C26—H26B	0.99	C71—C73	1.467 (8)
C27—C29	1.512 (7)	C71—C72	1.518 (6)
C27—C28	1.521 (6)	C71—C74	1.527 (8)
C27—H27	1	C72—H72A	0.98
C28—H28A	0.98	C72—H72B	0.98
C28—H28B	0.98	C72—H72C	0.98
C28—H28C	0.98	C73—H73A	0.98
C29—H29A	0.98	C73—H73B	0.98
C29—H29B	0.98	C73—H73C	0.98
C29—H29C	0.98	C74—H74A	0.98
C30—C31	1.517 (5)	C74—H74B	0.98
C30—H30A	0.99	C74—H74C	0.98
C30—H30B	0.99	O81—C82	1.352 (5)
C31—C34	1.502 (7)	O81—C86	1.452 (5)
C31—C32	1.513 (7)	C82—O95	1.220 (5)
C31—C33	1.521 (7)	C82—N83	1.339 (5)
C32—H32A	0.98	N83—N84	1.417 (4)
C32—H32B	0.98	N83—H83	0.89 (4)
C32—H32C	0.98	N84—C85	1.463 (5)
C33—H33A	0.98	N84—C90	1.473 (5)
C33—H33B	0.98	C85—C86	1.513 (6)
C33—H33C	0.98	C85—C87	1.522 (6)
C34—H34A	0.98	C85—H85	1
C34—H34B	0.98	C86—H86A	0.99
C34—H34C	0.98	C86—H86B	0.99
O41—C42	1.339 (4)	C87—C89	1.504 (7)
O41—C46	1.459 (5)	C87—C88	1.510 (7)
C42—O55	1.229 (4)	C87—H87	1
C42—N43	1.332 (5)	C88—H88A	0.98
N43—N44	1.417 (4)	C88—H88B	0.98
N43—H43	0.88 (4)	C88—H88C	0.98
N44—C45	1.473 (5)	C89—H89A	0.98
N44—C50	1.473 (6)	C89—H89B	0.98
C45—C46	1.512 (6)	C89—H89C	0.98
C45—C47	1.513 (7)	C90—C91	1.507 (6)
C45—H45	1	C90—H90A	0.99
C46—H46A	0.99	C90—H90B	0.99
C46—H46B	0.99	C91—C93	1.503 (7)
C47—C48	1.489 (8)	C91—C92	1.511 (7)
C47—C49	1.520 (8)	C91—C94	1.516 (8)
C47—H47	1	C92—H92A	0.98
C48—H48A	0.98	C92—H92B	0.98
C48—H48B	0.98	C92—H92C	0.98
C48—H48C	0.98	C93—H93A	0.98
C49—H49A	0.98	C93—H93B	0.98
C49—H49B	0.98	C93—H93C	0.98
C49—H49C	0.98	C94—H94A	0.98
C50—C51	1.507 (7)	C94—H94B	0.98
C50—H50A	0.99	C94—H94C	0.98
C50—H50B	0.99
C2—O1—C6	119.0 (3)	C54B—C51—C53A	74.9 (10)
O15—C2—N3	123.8 (6)	C50—C51—C53A	108.4 (7)
O15—C2—O1	119.1 (5)	C54B—C51—C52B	111.2 (12)
N3—C2—O1	117.1 (4)	C50—C51—C52B	116.6 (7)
C2—N3—N4	128.2 (4)	C53A—C51—C52B	129.3 (9)
C2—N3—H3	117 (3)	C52A—C51—C54A	108.8 (10)
N4—N3—H3	113 (4)	C50—C51—C54A	110.3 (7)
N3—N4—C5	107.6 (3)	C53A—C51—C54A	109.4 (10)
N3—N4—C10	111.4 (3)	C52B—C51—C54A	76.0 (10)
C5—N4—C10	114.8 (3)	C52A—C51—C53B	77.5 (10)
N4—C5—C6	108.3 (3)	C54B—C51—C53B	109.8 (11)
N4—C5—C7	110.9 (3)	C50—C51—C53B	109.2 (7)
C6—C5—C7	115.2 (3)	C52B—C51—C53B	103.4 (10)
N4—C5—H5	107.4	C54A—C51—C53B	135.5 (9)
C6—C5—H5	107.4	C51—C52A—H52A	109.5
C7—C5—H5	107.4	C51—C52A—H52B	109.5
O1—C6—C5	110.1 (3)	H52A—C52A—H52B	109.5
O1—C6—H6A	109.6	C51—C52A—H52C	109.5
C5—C6—H6A	109.6	H52A—C52A—H52C	109.5
O1—C6—H6B	109.6	H52B—C52A—H52C	109.5
C5—C6—H6B	109.6	C51—C53A—H53A	109.5
H6A—C6—H6B	108.2	C51—C53A—H53B	109.5
C9—C7—C5	110.8 (3)	H53A—C53A—H53B	109.5
C9—C7—C8	109.7 (3)	C51—C53A—H53C	109.5
C5—C7—C8	112.8 (3)	H53A—C53A—H53C	109.5
C9—C7—H7	107.8	H53B—C53A—H53C	109.5
C5—C7—H7	107.8	C51—C54A—H54A	109.5
C8—C7—H7	107.8	C51—C54A—H54B	109.5
C7—C8—H8A	109.5	H54A—C54A—H54B	109.5
C7—C8—H8B	109.5	C51—C54A—H54C	109.5
H8A—C8—H8B	109.5	H54A—C54A—H54C	109.5
C7—C8—H8C	109.5	H54B—C54A—H54C	109.5
H8A—C8—H8C	109.5	C51—C52B—H52D	109.5
H8B—C8—H8C	109.5	C51—C52B—H52E	109.5
C7—C9—H9A	109.5	H52D—C52B—H52E	109.5
C7—C9—H9B	109.5	C51—C52B—H52F	109.5
H9A—C9—H9B	109.5	H52D—C52B—H52F	109.5
C7—C9—H9C	109.5	H52E—C52B—H52F	109.5
H9A—C9—H9C	109.5	C51—C53B—H53D	109.5
H9B—C9—H9C	109.5	C51—C53B—H53E	109.5
N4—C10—C11	112.3 (3)	H53D—C53B—H53E	109.5
N4—C10—H10A	109.1	C51—C53B—H53F	109.5
C11—C10—H10A	109.1	H53D—C53B—H53F	109.5
N4—C10—H10B	109.1	H53E—C53B—H53F	109.5
C11—C10—H10B	109.1	C51—C54B—H54D	109.5
H10A—C10—H10B	107.9	C51—C54B—H54E	109.5
C14—C11—C13	110.9 (4)	H54D—C54B—H54E	109.5
C14—C11—C12	108.8 (4)	C51—C54B—H54F	109.5
C13—C11—C12	109.8 (3)	H54D—C54B—H54F	109.5
C14—C11—C10	110.1 (3)	H54E—C54B—H54F	109.5
C13—C11—C10	109.9 (4)	C62—O61—C66	120.5 (3)
C12—C11—C10	107.2 (3)	O75—C62—N63	123.2 (4)
C11—C12—H12A	109.5	O75—C62—O61	119.1 (4)
C11—C12—H12B	109.5	N63—C62—O61	117.7 (4)
H12A—C12—H12B	109.5	C62—N63—N64	126.6 (3)
C11—C12—H12C	109.5	C62—N63—H63	122 (3)
H12A—C12—H12C	109.5	N64—N63—H63	110 (3)
H12B—C12—H12C	109.5	N63—N64—C70	111.7 (3)
C11—C13—H13A	109.5	N63—N64—C65	107.8 (3)
C11—C13—H13B	109.5	C70—N64—C65	113.6 (3)
H13A—C13—H13B	109.5	N64—C65—C66	108.2 (3)
C11—C13—H13C	109.5	N64—C65—C67	110.8 (4)
H13A—C13—H13C	109.5	C66—C65—C67	114.8 (4)
H13B—C13—H13C	109.5	N64—C65—H65	107.6
C11—C14—H14A	109.5	C66—C65—H65	107.6
C11—C14—H14B	109.5	C67—C65—H65	107.6
H14A—C14—H14B	109.5	O61—C66—C65	111.7 (4)
C11—C14—H14C	109.5	O61—C66—H66A	109.3
H14A—C14—H14C	109.5	C65—C66—H66A	109.3
H14B—C14—H14C	109.5	O61—C66—H66B	109.3
C22—O21—C26	118.6 (3)	C65—C66—H66B	109.3
O35—C22—N23	123.0 (4)	H66A—C66—H66B	107.9
O35—C22—O21	118.3 (3)	C69—C67—C65	112.2 (4)
N23—C22—O21	118.6 (4)	C69—C67—C68	110.8 (5)
C22—N23—N24	127.2 (4)	C65—C67—C68	109.9 (5)
C22—N23—H23	114 (3)	C69—C67—H67	107.9
N24—N23—H23	118 (3)	C65—C67—H67	107.9
N23—N24—C25	108.1 (3)	C68—C67—H67	107.9
N23—N24—C30	110.9 (3)	C67—C68—H68A	109.5
C25—N24—C30	114.3 (3)	C67—C68—H68B	109.5
N24—C25—C26	108.7 (3)	H68A—C68—H68B	109.5
N24—C25—C27	111.3 (3)	C67—C68—H68C	109.5
C26—C25—C27	114.0 (3)	H68A—C68—H68C	109.5
N24—C25—H25	107.5	H68B—C68—H68C	109.5
C26—C25—H25	107.5	C67—C69—H69A	109.5
C27—C25—H25	107.5	C67—C69—H69B	109.5
O21—C26—C25	109.8 (3)	H69A—C69—H69B	109.5
O21—C26—H26A	109.7	C67—C69—H69C	109.5
C25—C26—H26A	109.7	H69A—C69—H69C	109.5
O21—C26—H26B	109.7	H69B—C69—H69C	109.5
C25—C26—H26B	109.7	N64—C70—C71	114.0 (3)
H26A—C26—H26B	108.2	N64—C70—H70A	108.8
C29—C27—C28	110.4 (4)	C71—C70—H70A	108.8
C29—C27—C25	110.7 (3)	N64—C70—H70B	108.8
C28—C27—C25	110.4 (4)	C71—C70—H70B	108.8
C29—C27—H27	108.4	H70A—C70—H70B	107.7
C28—C27—H27	108.4	C73—C71—C70	111.9 (4)
C25—C27—H27	108.4	C73—C71—C72	110.0 (4)
C27—C28—H28A	109.5	C70—C71—C72	108.5 (4)
C27—C28—H28B	109.5	C73—C71—C74	111.7 (6)
H28A—C28—H28B	109.5	C70—C71—C74	106.9 (4)
C27—C28—H28C	109.5	C72—C71—C74	107.5 (5)
H28A—C28—H28C	109.5	C71—C72—H72A	109.5
H28B—C28—H28C	109.5	C71—C72—H72B	109.5
C27—C29—H29A	109.5	H72A—C72—H72B	109.5
C27—C29—H29B	109.5	C71—C72—H72C	109.5
H29A—C29—H29B	109.5	H72A—C72—H72C	109.5
C27—C29—H29C	109.5	H72B—C72—H72C	109.5
H29A—C29—H29C	109.5	C71—C73—H73A	109.5
H29B—C29—H29C	109.5	C71—C73—H73B	109.5
N24—C30—C31	113.1 (3)	H73A—C73—H73B	109.5
N24—C30—H30A	109	C71—C73—H73C	109.5
C31—C30—H30A	109	H73A—C73—H73C	109.5
N24—C30—H30B	109	H73B—C73—H73C	109.5
C31—C30—H30B	109	C71—C74—H74A	109.5
H30A—C30—H30B	107.8	C71—C74—H74B	109.5
C34—C31—C32	108.5 (4)	H74A—C74—H74B	109.5
C34—C31—C30	109.5 (4)	C71—C74—H74C	109.5
C32—C31—C30	108.4 (4)	H74A—C74—H74C	109.5
C34—C31—C33	110.1 (5)	H74B—C74—H74C	109.5
C32—C31—C33	110.9 (4)	C82—O81—C86	119.8 (3)
C30—C31—C33	109.5 (4)	O95—C82—N83	123.3 (4)
C31—C32—H32A	109.5	O95—C82—O81	118.1 (4)
C31—C32—H32B	109.5	N83—C82—O81	118.6 (4)
H32A—C32—H32B	109.5	C82—N83—N84	125.2 (3)
C31—C32—H32C	109.5	C82—N83—H83	115 (3)
H32A—C32—H32C	109.5	N84—N83—H83	118 (3)
H32B—C32—H32C	109.5	N83—N84—C85	108.3 (3)
C31—C33—H33A	109.5	N83—N84—C90	110.5 (3)
C31—C33—H33B	109.5	C85—N84—C90	113.6 (3)
H33A—C33—H33B	109.5	N84—C85—C86	107.9 (3)
C31—C33—H33C	109.5	N84—C85—C87	111.1 (3)
H33A—C33—H33C	109.5	C86—C85—C87	115.0 (4)
H33B—C33—H33C	109.5	N84—C85—H85	107.5
C31—C34—H34A	109.5	C86—C85—H85	107.5
C31—C34—H34B	109.5	C87—C85—H85	107.5
H34A—C34—H34B	109.5	O81—C86—C85	111.4 (3)
C31—C34—H34C	109.5	O81—C86—H86A	109.3
H34A—C34—H34C	109.5	C85—C86—H86A	109.3
H34B—C34—H34C	109.5	O81—C86—H86B	109.3
C42—O41—C46	119.1 (3)	C85—C86—H86B	109.3
O55—C42—N43	122.5 (4)	H86A—C86—H86B	108
O55—C42—O41	118.0 (3)	C89—C87—C88	109.1 (4)
N43—C42—O41	119.6 (3)	C89—C87—C85	110.7 (4)
C42—N43—N44	125.8 (3)	C88—C87—C85	113.0 (4)
C42—N43—H43	117 (2)	C89—C87—H87	108
N44—N43—H43	113 (2)	C88—C87—H87	108
N43—N44—C45	108.2 (3)	C85—C87—H87	108
N43—N44—C50	111.2 (4)	C87—C88—H88A	109.5
C45—N44—C50	114.5 (3)	C87—C88—H88B	109.5
N44—C45—C46	108.4 (3)	H88A—C88—H88B	109.5
N44—C45—C47	110.2 (3)	C87—C88—H88C	109.5
C46—C45—C47	116.0 (4)	H88A—C88—H88C	109.5
N44—C45—H45	107.3	H88B—C88—H88C	109.5
C46—C45—H45	107.3	C87—C89—H89A	109.5
C47—C45—H45	107.3	C87—C89—H89B	109.5
O41—C46—C45	109.6 (3)	H89A—C89—H89B	109.5
O41—C46—H46A	109.7	C87—C89—H89C	109.5
C45—C46—H46A	109.7	H89A—C89—H89C	109.5
O41—C46—H46B	109.7	H89B—C89—H89C	109.5
C45—C46—H46B	109.7	N84—C90—C91	114.5 (3)
H46A—C46—H46B	108.2	N84—C90—H90A	108.6
C48—C47—C45	112.4 (5)	C91—C90—H90A	108.6
C48—C47—C49	110.1 (5)	N84—C90—H90B	108.6
C45—C47—C49	111.6 (4)	C91—C90—H90B	108.6
C48—C47—H47	107.5	H90A—C90—H90B	107.6
C45—C47—H47	107.5	C93—C91—C90	112.8 (4)
C49—C47—H47	107.5	C93—C91—C92	111.7 (5)
C47—C48—H48A	109.5	C90—C91—C92	108.6 (4)
C47—C48—H48B	109.5	C93—C91—C94	107.7 (6)
H48A—C48—H48B	109.5	C90—C91—C94	108.8 (4)
C47—C48—H48C	109.5	C92—C91—C94	107.0 (5)
H48A—C48—H48C	109.5	C91—C92—H92A	109.5
H48B—C48—H48C	109.5	C91—C92—H92B	109.5
C47—C49—H49A	109.5	H92A—C92—H92B	109.5
C47—C49—H49B	109.5	C91—C92—H92C	109.5
H49A—C49—H49B	109.5	H92A—C92—H92C	109.5
C47—C49—H49C	109.5	H92B—C92—H92C	109.5
H49A—C49—H49C	109.5	C91—C93—H93A	109.5
H49B—C49—H49C	109.5	C91—C93—H93B	109.5
N44—C50—C51	115.2 (4)	H93A—C93—H93B	109.5
N44—C50—H50A	108.5	C91—C93—H93C	109.5
C51—C50—H50A	108.5	H93A—C93—H93C	109.5
N44—C50—H50B	108.5	H93B—C93—H93C	109.5
C51—C50—H50B	108.5	C91—C94—H94A	109.5
H50A—C50—H50B	107.5	C91—C94—H94B	109.5
C52A—C51—C54B	140.4 (13)	H94A—C94—H94B	109.5
C52A—C51—C50	107.3 (8)	C91—C94—H94C	109.5
C54B—C51—C50	106.5 (9)	H94A—C94—H94C	109.5
C52A—C51—C53A	112.6 (9)	H94B—C94—H94C	109.5
C6—O1—C2—O15	−179.7 (4)	N44—C45—C47—C48	176.2 (5)
C6—O1—C2—N3	−1.4 (6)	C46—C45—C47—C48	52.6 (6)
O15—C2—N3—N4	171.3 (4)	N44—C45—C47—C49	−59.5 (5)
O1—C2—N3—N4	−6.9 (7)	C46—C45—C47—C49	176.8 (4)
C2—N3—N4—C5	−20.3 (6)	N43—N44—C50—C51	81.6 (5)
C2—N3—N4—C10	106.3 (5)	C45—N44—C50—C51	−155.4 (4)
N3—N4—C5—C6	52.0 (4)	N44—C50—C51—C52A	−86.4 (8)
C10—N4—C5—C6	−72.6 (4)	N44—C50—C51—C54B	72.6 (10)
N3—N4—C5—C7	−75.3 (4)	N44—C50—C51—C53A	151.8 (8)
C10—N4—C5—C7	160.1 (3)	N44—C50—C51—C52B	−52.1 (10)
C2—O1—C6—C5	35.1 (5)	N44—C50—C51—C54A	32.0 (9)
N4—C5—C6—O1	−61.2 (4)	N44—C50—C51—C53B	−168.8 (9)
C7—C5—C6—O1	63.5 (4)	C66—O61—C62—O75	−178.0 (4)
N4—C5—C7—C9	−60.6 (4)	C66—O61—C62—N63	1.6 (6)
C6—C5—C7—C9	176.0 (4)	O75—C62—N63—N64	178.0 (4)
N4—C5—C7—C8	175.9 (3)	O61—C62—N63—N64	−1.5 (6)
C6—C5—C7—C8	52.6 (5)	C62—N63—N64—C70	97.4 (4)
N3—N4—C10—C11	118.9 (4)	C62—N63—N64—C65	−28.1 (5)
C5—N4—C10—C11	−118.5 (4)	N63—N64—C65—C66	54.1 (4)
N4—C10—C11—C14	62.7 (4)	C70—N64—C65—C66	−70.2 (4)
N4—C10—C11—C13	−59.7 (4)	N63—N64—C65—C67	−72.5 (4)
N4—C10—C11—C12	−179.0 (3)	C70—N64—C65—C67	163.2 (3)
C26—O21—C22—O35	177.6 (4)	C62—O61—C66—C65	28.0 (6)
C26—O21—C22—N23	−6.0 (6)	N64—C65—C66—O61	−56.3 (4)
O35—C22—N23—N24	173.1 (4)	C67—C65—C66—O61	68.0 (4)
O21—C22—N23—N24	−3.2 (6)	N64—C65—C67—C69	−48.6 (5)
C22—N23—N24—C25	−21.1 (5)	C66—C65—C67—C69	−171.5 (4)
C22—N23—N24—C30	104.9 (5)	N64—C65—C67—C68	−172.3 (4)
N23—N24—C25—C26	50.9 (4)	C66—C65—C67—C68	64.8 (5)
C30—N24—C25—C26	−73.1 (4)	N63—N64—C70—C71	105.7 (4)
N23—N24—C25—C27	−75.6 (4)	C65—N64—C70—C71	−132.2 (4)
C30—N24—C25—C27	160.5 (3)	N64—C70—C71—C73	−61.7 (6)
C22—O21—C26—C25	37.7 (5)	N64—C70—C71—C72	176.7 (4)
N24—C25—C26—O21	−60.8 (4)	N64—C70—C71—C74	61.0 (6)
C27—C25—C26—O21	64.0 (4)	C86—O81—C82—O95	−175.7 (4)
N24—C25—C27—C29	−57.2 (4)	C86—O81—C82—N83	3.1 (6)
C26—C25—C27—C29	179.3 (4)	O95—C82—N83—N84	178.4 (4)
N24—C25—C27—C28	−179.8 (3)	O81—C82—N83—N84	−0.4 (6)
C26—C25—C27—C28	56.8 (5)	C82—N83—N84—C85	−31.3 (5)
N23—N24—C30—C31	120.1 (4)	C82—N83—N84—C90	93.7 (4)
C25—N24—C30—C31	−117.4 (4)	N83—N84—C85—C86	56.7 (4)
N24—C30—C31—C34	61.6 (5)	C90—N84—C85—C86	−66.5 (4)
N24—C30—C31—C32	179.8 (4)	N83—N84—C85—C87	−70.3 (4)
N24—C30—C31—C33	−59.2 (5)	C90—N84—C85—C87	166.5 (3)
C46—O41—C42—O55	−178.8 (4)	C82—O81—C86—C85	25.6 (6)
C46—O41—C42—N43	1.0 (6)	N84—C85—C86—O81	−55.8 (4)
O55—C42—N43—N44	174.1 (4)	C87—C85—C86—O81	68.9 (4)
O41—C42—N43—N44	−5.7 (6)	N84—C85—C87—C89	−54.8 (5)
C42—N43—N44—C45	−23.6 (5)	C86—C85—C87—C89	−177.8 (4)
C42—N43—N44—C50	102.9 (5)	N84—C85—C87—C88	−177.5 (4)
N43—N44—C45—C46	54.1 (4)	C86—C85—C87—C88	59.5 (5)
C50—N44—C45—C46	−70.5 (4)	N83—N84—C90—C91	91.5 (4)
N43—N44—C45—C47	−73.9 (4)	C85—N84—C90—C91	−146.5 (4)
C50—N44—C45—C47	161.6 (4)	N84—C90—C91—C93	−55.0 (6)
C42—O41—C46—C45	31.4 (5)	N84—C90—C91—C92	−179.4 (4)
N44—C45—C46—O41	−59.2 (5)	N84—C90—C91—C94	64.5 (5)
C47—C45—C46—O41	65.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N23—H23···O55i	0.78 (4)	2.16 (4)	2.937 (5)	177 (5)
N43—H43···O35ii	0.88 (4)	1.99 (4)	2.868 (5)	175 (3)
N63—H63···O95iii	0.84 (4)	2.13 (4)	2.949 (5)	163 (3)
N83—H83···O75iv	0.89 (4)	2.04 (4)	2.926 (4)	175 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N23—H23⋯O55i	0.78 (4)	2.16 (4)	2.937 (5)	177 (5)
N43—H43⋯O35ii	0.88 (4)	1.99 (4)	2.868 (5)	175 (3)
N63—H63⋯O95iii	0.84 (4)	2.13 (4)	2.949 (5)	163 (3)
N83—H83⋯O75iv	0.89 (4)	2.04 (4)	2.926 (4)	175 (4)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .