5,10,10,15,20,20-Hexamethylcalix[4]pyrrole 5,15-diethyl diester.

In the title compound, C(32)H(40)N(4)O(4), the pyrrole rings and ester groups adopt a 1,3-alternate conformation in which the alternating pyrrole and ester units are in opposite directions. The structure displays N-H⋯O hydrogen bonding and exhibits disorder [site occupancies of 0.81(2) and 0.71(2)] in the peripheral ethyl groups.

Related literature

For related calix[4]pyrrole structures see: Gale et al. (1998 ▶, 2001 ▶). For the synthesis of mono- and di-ester functionalized calix[4]pyrrole structures, see: Akar & Aydogan (2005 ▶). For applications of calix[4]pyrroles, see: Varo et al. (1996 ▶); Beer & Gale (2001 ▶); Nishiyabu & Pavel Anzenbacher (2005 ▶); Miyaji et al. (1999 ▶); Nielsen et al. (2004 ▶); Sessler et al. (1998 ▶).

Experimental

Crystal data

C32H40N4O4

M = 544.68

Monoclinic,

a = 10.4392 (3) Å

b = 11.6453 (3) Å

c = 24.0488 (7) Å

β = 95.380 (2)°

V = 2910.68 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 153 K

0.30 × 0.30 × 0.23 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

11684 measured reflections

6619 independent reflections

2971 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.135

S = 1.09

6619 reflections

390 parameters

12 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.30 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: COLLECT; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXTL/PC (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC; software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809048260/om2288sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048260/om2288Isup2.hkl

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

C32H40N4O4	F(000) = 1168
Mr = 544.68	Dx = 1.243 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.4392 (3) Å	Cell parameters from 5852 reflections
b = 11.6453 (3) Å	θ = 2.9–27.5°
c = 24.0488 (7) Å	µ = 0.08 mm−1
β = 95.380 (2)°	T = 153 K
V = 2910.68 (14) Å3	Prisms, yellow
Z = 4	0.30 × 0.30 × 0.23 mm

Nonius KappaCCD diffractometer	2971 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.064
graphite	θmax = 27.5°, θmin = 3.0°
ω scans	h = −13→13
11684 measured reflections	k = −15→15
6619 independent reflections	l = −31→31

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.044P)2] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.035
6619 reflections	Δρmax = 0.26 e Å−3
390 parameters	Δρmin = −0.30 e Å−3
12 restraints	Extinction correction: SHELXTL/PC (Sheldrick, 1998), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0023 (5)

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.Both methyl groups on the ester moieties were disordered about two orientations. The disorder was modeled in the same way for both groups. The site occupancy for one carbon atom orientation was assigned a variable x. The site occupancy factor for the other conformer was assigned the variable (1 - x). The variable x was refined while refining the two atoms with a single isotropic displacement parameter. At the same time, the geometry of the methyl carbon atoms were restrained to be equivalent. In this way, the site occupancy factor for C36 refined to 81 (2)% and that for C28 refined to 77 (2)%. The lower occupancy carbon atoms, C28A and C36A, were refined isotropically.

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.41232 (19)	0.58854 (17)	0.12330 (8)	0.0335 (5)
N2	0.57872 (18)	0.40469 (18)	0.21083 (8)	0.0320 (5)
N3	0.86084 (19)	0.48641 (18)	0.15438 (9)	0.0364 (5)
N4	0.69557 (17)	0.70790 (17)	0.08407 (9)	0.0332 (5)
C1	0.41029 (19)	0.70290 (18)	0.10945 (9)	0.0294 (6)
C2	0.3522 (2)	0.7587 (2)	0.14962 (9)	0.0353 (6)
H2	0.3358	0.8397	0.1507	0.042*
C3	0.3188 (2)	0.6765 (2)	0.18906 (10)	0.0351 (6)
H3	0.2777	0.6920	0.2224	0.042*
C4	0.35692 (19)	0.57116 (19)	0.17249 (9)	0.0289 (6)
C5	0.3415 (2)	0.45208 (18)	0.19602 (9)	0.0296 (6)
C6	0.4570 (2)	0.38006 (19)	0.18602 (9)	0.0302 (6)
C7	0.4680 (2)	0.2850 (2)	0.15386 (10)	0.0373 (6)
H7	0.3987	0.2475	0.1319	0.045*
C8	0.5988 (2)	0.2511 (2)	0.15865 (10)	0.0394 (6)
H8	0.6346	0.1872	0.1401	0.047*
C9	0.6660 (2)	0.32472 (19)	0.19419 (9)	0.0312 (6)
C10	0.8051 (2)	0.3271 (2)	0.21892 (10)	0.0372 (6)
C11	0.8675 (2)	0.4401 (2)	0.20719 (10)	0.0343 (6)
C12	0.9319 (2)	0.5184 (2)	0.24153 (10)	0.0398 (6)
H12	0.9505	0.5087	0.2811	0.048*
C13	0.9654 (2)	0.6129 (2)	0.20934 (10)	0.0395 (6)
H13	1.0120	0.6799	0.2229	0.047*
C14	0.9206 (2)	0.5919 (2)	0.15496 (10)	0.0324 (6)
C15	0.9303 (2)	0.65566 (19)	0.10072 (10)	0.0357 (6)
C16	0.8010 (2)	0.65376 (19)	0.06609 (10)	0.0314 (6)
C17	0.7601 (2)	0.6029 (2)	0.01682 (10)	0.0412 (7)
H17	0.8129	0.5597	−0.0062	0.049*
C18	0.6277 (2)	0.6277 (2)	0.00454 (10)	0.0412 (6)
H18	0.5728	0.6012	−0.0272	0.049*
C19	0.5895 (2)	0.69349 (18)	0.04663 (9)	0.0282 (5)
C20	0.4601 (2)	0.74499 (18)	0.05557 (9)	0.0290 (6)
C21	0.2204 (2)	0.39553 (19)	0.16701 (10)	0.0388 (6)
H21A	0.2292	0.3889	0.1278	0.058*
H21B	0.2085	0.3206	0.1824	0.058*
H21C	0.1472	0.4427	0.1725	0.058*
C22	0.3263 (2)	0.46188 (19)	0.25879 (9)	0.0380 (6)
H22A	0.4022	0.4963	0.2774	0.057*
H22B	0.2529	0.5089	0.2642	0.057*
H22C	0.3143	0.3869	0.2740	0.057*
C23	0.8124 (2)	0.3064 (2)	0.28177 (10)	0.0464 (7)
H23A	0.7728	0.3686	0.3000	0.070*
H23B	0.7676	0.2362	0.2881	0.070*
H23C	0.9006	0.2994	0.2967	0.070*
C24	0.8709 (2)	0.2257 (2)	0.19279 (11)	0.0450 (7)
O25	0.89367 (17)	0.13441 (17)	0.21515 (8)	0.0633 (6)
O26	0.89694 (16)	0.24818 (15)	0.14039 (7)	0.0576 (5)
C27	0.9610 (3)	0.1595 (3)	0.11130 (14)	0.0835 (11)
H27C	1.0493	0.1554	0.1263	0.100*	0.23
H27D	0.9216	0.0867	0.1176	0.100*	0.23
H27A	1.0173	0.1177	0.1379	0.100*	0.77
H27B	1.0123	0.1939	0.0847	0.100*	0.77
C28	0.8770 (4)	0.0833 (3)	0.08351 (19)	0.0866 (14)	0.77
H28A	0.9235	0.0259	0.0650	0.130*	0.77
H28B	0.8272	0.0472	0.1102	0.130*	0.77
H28C	0.8206	0.1239	0.0564	0.130*	0.77
C28A	0.9568 (12)	0.1779 (10)	0.0542 (3)	0.065 (4)*	0.23
H28D	1.0006	0.1173	0.0366	0.098*	0.23
H28E	0.8686	0.1806	0.0388	0.098*	0.23
H28F	0.9976	0.2499	0.0476	0.098*	0.23
C29	1.0315 (2)	0.5981 (2)	0.06754 (10)	0.0445 (7)
H29A	1.0052	0.5207	0.0588	0.067*
H29B	1.0404	0.6396	0.0336	0.067*
H29C	1.1126	0.5973	0.0900	0.067*
C30	0.9734 (2)	0.7806 (2)	0.11352 (11)	0.0475 (7)
H30A	0.9107	0.8184	0.1338	0.071*
H30B	1.0547	0.7791	0.1358	0.071*
H30C	0.9825	0.8214	0.0794	0.071*
C31	0.3626 (2)	0.7138 (2)	0.00625 (9)	0.0401 (6)
H31A	0.3936	0.7393	−0.0280	0.060*
H31B	0.3514	0.6320	0.0051	0.060*
H31C	0.2817	0.7500	0.0108	0.060*
C32	0.4738 (2)	0.8754 (2)	0.06379 (10)	0.0350 (6)
O33	0.56342 (17)	0.92236 (14)	0.08880 (7)	0.0483 (5)
O34	0.36920 (15)	0.93043 (13)	0.04203 (7)	0.0469 (5)
C35	0.3633 (3)	1.0521 (2)	0.05480 (13)	0.0615 (9)
H35C	0.4456	1.0784	0.0710	0.074*	0.19
H35D	0.3400	1.0956	0.0214	0.074*	0.19
H35A	0.4335	1.0915	0.0401	0.074*	0.81
H35B	0.3700	1.0626	0.0946	0.074*	0.81
C36	0.2440 (3)	1.0986 (3)	0.03141 (18)	0.0751 (13)	0.81
H36A	0.2399	1.1790	0.0399	0.113*	0.81
H36B	0.2374	1.0882	−0.0084	0.113*	0.81
H36C	0.1744	1.0593	0.0466	0.113*	0.81
C36A	0.2700 (13)	1.0685 (10)	0.0931 (6)	0.072 (5)*	0.19
H36D	0.2637	1.1482	0.1026	0.109*	0.19
H36E	0.1882	1.0420	0.0764	0.109*	0.19
H36F	0.2944	1.0247	0.1262	0.109*	0.19
H1N	0.453 (2)	0.5350 (18)	0.1093 (9)	0.031 (7)*
H2N	0.600 (2)	0.4638 (19)	0.2312 (9)	0.040 (8)*
H3N	0.819 (2)	0.4537 (18)	0.1267 (9)	0.029 (7)*
H4N	0.698 (2)	0.752 (2)	0.1135 (10)	0.053 (8)*

	U11	U22	U33	U12	U13	U23
N1	0.0380 (12)	0.0285 (13)	0.0356 (13)	0.0067 (10)	0.0116 (10)	−0.0012 (10)
N2	0.0303 (12)	0.0319 (13)	0.0334 (12)	−0.0028 (10)	0.0021 (10)	−0.0029 (10)
N3	0.0301 (12)	0.0465 (14)	0.0320 (14)	−0.0011 (11)	−0.0003 (10)	0.0010 (12)
N4	0.0322 (13)	0.0405 (13)	0.0268 (12)	0.0038 (10)	0.0030 (10)	−0.0034 (11)
C1	0.0247 (12)	0.0273 (14)	0.0361 (15)	0.0016 (10)	0.0027 (11)	0.0029 (12)
C2	0.0340 (14)	0.0289 (13)	0.0448 (16)	0.0060 (11)	0.0126 (12)	0.0005 (13)
C3	0.0334 (14)	0.0359 (15)	0.0383 (15)	0.0029 (12)	0.0144 (12)	0.0002 (12)
C4	0.0222 (12)	0.0340 (14)	0.0310 (14)	0.0021 (11)	0.0047 (11)	0.0008 (12)
C5	0.0262 (13)	0.0306 (14)	0.0322 (14)	−0.0004 (11)	0.0046 (11)	0.0013 (11)
C6	0.0269 (14)	0.0312 (14)	0.0319 (14)	−0.0026 (11)	−0.0001 (11)	0.0037 (12)
C7	0.0354 (15)	0.0376 (15)	0.0374 (15)	0.0017 (12)	−0.0038 (12)	−0.0049 (13)
C8	0.0394 (15)	0.0387 (15)	0.0398 (16)	0.0105 (13)	0.0030 (12)	−0.0015 (13)
C9	0.0293 (14)	0.0355 (14)	0.0294 (14)	0.0053 (12)	0.0058 (11)	0.0063 (12)
C10	0.0292 (14)	0.0507 (16)	0.0324 (15)	0.0067 (12)	0.0064 (11)	0.0080 (13)
C11	0.0253 (13)	0.0509 (16)	0.0270 (15)	0.0044 (12)	0.0046 (11)	0.0087 (13)
C12	0.0339 (15)	0.0558 (17)	0.0296 (15)	0.0063 (13)	0.0021 (12)	0.0009 (14)
C13	0.0327 (14)	0.0479 (17)	0.0379 (16)	−0.0016 (12)	0.0030 (12)	−0.0064 (14)
C14	0.0219 (13)	0.0361 (15)	0.0396 (16)	0.0045 (11)	0.0045 (11)	0.0032 (12)
C15	0.0295 (14)	0.0411 (15)	0.0375 (15)	0.0029 (11)	0.0093 (12)	0.0058 (13)
C16	0.0275 (13)	0.0365 (14)	0.0314 (15)	0.0033 (11)	0.0097 (12)	0.0049 (12)
C17	0.0393 (16)	0.0466 (16)	0.0389 (16)	0.0074 (13)	0.0094 (13)	−0.0089 (13)
C18	0.0388 (16)	0.0494 (16)	0.0345 (15)	0.0012 (13)	−0.0014 (12)	−0.0119 (13)
C19	0.0305 (13)	0.0290 (13)	0.0254 (13)	0.0001 (11)	0.0037 (11)	0.0025 (11)
C20	0.0301 (13)	0.0274 (13)	0.0298 (14)	0.0013 (11)	0.0034 (11)	0.0005 (11)
C21	0.0287 (14)	0.0377 (15)	0.0497 (16)	−0.0001 (11)	0.0014 (12)	0.0029 (12)
C22	0.0345 (14)	0.0382 (15)	0.0425 (16)	−0.0006 (12)	0.0100 (12)	0.0067 (12)
C23	0.0375 (15)	0.0659 (18)	0.0349 (15)	−0.0033 (13)	−0.0011 (12)	0.0147 (14)
C24	0.0305 (15)	0.0565 (19)	0.0478 (18)	0.0063 (13)	0.0030 (13)	0.0123 (16)
O25	0.0570 (13)	0.0590 (13)	0.0736 (15)	0.0257 (10)	0.0044 (10)	0.0218 (11)
O26	0.0627 (12)	0.0598 (12)	0.0536 (13)	0.0199 (10)	0.0230 (10)	0.0037 (10)
C27	0.089 (3)	0.082 (3)	0.082 (3)	0.036 (2)	0.026 (2)	−0.015 (2)
C28	0.087 (3)	0.070 (3)	0.098 (4)	0.034 (3)	−0.015 (3)	−0.025 (3)
C29	0.0347 (15)	0.0597 (18)	0.0408 (16)	0.0062 (13)	0.0123 (12)	0.0075 (14)
C30	0.0375 (15)	0.0481 (17)	0.0568 (18)	−0.0038 (13)	0.0043 (13)	0.0081 (14)
C31	0.0380 (15)	0.0440 (15)	0.0379 (16)	0.0027 (12)	0.0005 (12)	0.0045 (13)
C32	0.0332 (15)	0.0375 (15)	0.0352 (15)	0.0027 (13)	0.0084 (12)	0.0042 (13)
O33	0.0475 (11)	0.0368 (10)	0.0592 (13)	−0.0056 (9)	−0.0024 (9)	−0.0044 (9)
O34	0.0428 (11)	0.0307 (10)	0.0671 (13)	0.0075 (8)	0.0047 (9)	0.0049 (9)
C35	0.069 (2)	0.0301 (16)	0.088 (2)	0.0102 (14)	0.0207 (18)	0.0045 (15)
C36	0.051 (2)	0.045 (2)	0.129 (4)	0.0151 (19)	0.010 (2)	0.008 (2)

N1—C1	1.372 (3)	C21—H21A	0.9601
N1—C4	1.379 (3)	C21—H21B	0.9600
N1—H1N	0.84 (2)	C21—H21C	0.9600
N2—C6	1.382 (3)	C22—H22A	0.9600
N2—C9	1.387 (3)	C22—H22B	0.9600
N2—H2N	0.86 (2)	C22—H22C	0.9600
N3—C11	1.376 (3)	C23—H23A	0.9600
N3—C14	1.377 (3)	C23—H23B	0.9600
N3—H3N	0.85 (2)	C23—H23C	0.9600
N4—C19	1.370 (3)	C24—O25	1.205 (3)
N4—C16	1.373 (3)	C24—O26	1.340 (3)
N4—H4N	0.87 (2)	O26—C27	1.446 (3)
C1—C2	1.354 (3)	C27—C28	1.375 (4)
C1—C20	1.522 (3)	C27—C28A	1.387 (7)
C2—C3	1.414 (3)	C27—H27C	0.9599
C2—H2	0.9601	C27—H27D	0.9600
C3—C4	1.360 (3)	C27—H27A	0.9600
C3—H3	0.9602	C27—H27B	0.9601
C4—C5	1.512 (3)	C28—H28A	0.9600
C5—C6	1.507 (3)	C28—H28B	0.9601
C5—C21	1.534 (3)	C28—H28C	0.9600
C5—C22	1.537 (3)	C28A—H28D	0.9601
C6—C7	1.361 (3)	C28A—H28E	0.9600
C7—C8	1.417 (3)	C28A—H28F	0.9600
C7—H7	0.9600	C29—H29A	0.9600
C8—C9	1.358 (3)	C29—H29B	0.9597
C8—H8	0.9600	C29—H29C	0.9602
C9—C10	1.518 (3)	C30—H30A	0.9600
C10—C11	1.506 (3)	C30—H30B	0.9600
C10—C23	1.526 (3)	C30—H30C	0.9600
C10—C24	1.531 (3)	C31—H31A	0.9603
C11—C12	1.364 (3)	C31—H31B	0.9600
C12—C13	1.409 (3)	C31—H31C	0.9599
C12—H12	0.9601	C32—O33	1.196 (3)
C13—C14	1.369 (3)	C32—O34	1.330 (3)
C13—H13	0.9600	O34—C35	1.453 (3)
C14—C15	1.513 (3)	C35—C36A	1.414 (7)
C15—C16	1.518 (3)	C35—C36	1.424 (4)
C15—C29	1.537 (3)	C35—H35C	0.9600
C15—C30	1.545 (3)	C35—H35D	0.9599
C16—C17	1.358 (3)	C35—H35A	0.9599
C17—C18	1.416 (3)	C35—H35B	0.9604
C17—H17	0.9598	C36—H36A	0.9601
C18—C19	1.359 (3)	C36—H36B	0.9600
C18—H18	0.9599	C36—H36C	0.9600
C19—C20	1.512 (3)	C36A—H36D	0.9600
C20—C31	1.532 (3)	C36A—H36E	0.9601
C20—C32	1.536 (3)	C36A—H36F	0.9601
C1—N1—C4	110.63 (19)	C5—C22—H22A	109.3
C1—N1—H1N	128.3 (14)	C5—C22—H22B	109.4
C4—N1—H1N	120.1 (15)	H22A—C22—H22B	109.5
C6—N2—C9	109.7 (2)	C5—C22—H22C	109.7
C6—N2—H2N	125.8 (15)	H22A—C22—H22C	109.5
C9—N2—H2N	124.2 (15)	H22B—C22—H22C	109.5
C11—N3—C14	110.9 (2)	C10—C23—H23A	110.4
C11—N3—H3N	121.6 (15)	C10—C23—H23B	108.2
C14—N3—H3N	127.3 (15)	H23A—C23—H23B	109.5
C19—N4—C16	111.1 (2)	C10—C23—H23C	109.8
C19—N4—H4N	124.6 (16)	H23A—C23—H23C	109.5
C16—N4—H4N	123.9 (16)	H23B—C23—H23C	109.5
C2—C1—N1	106.9 (2)	O25—C24—O26	122.9 (2)
C2—C1—C20	131.7 (2)	O25—C24—C10	125.1 (2)
N1—C1—C20	121.36 (19)	O26—C24—C10	112.0 (2)
C1—C2—C3	108.0 (2)	C24—O26—C27	117.3 (2)
C1—C2—H2	125.7	C28—C27—O26	113.2 (3)
C3—C2—H2	126.3	C28A—C27—O26	113.3 (5)
C4—C3—C2	108.44 (19)	C28A—C27—H27C	108.7
C4—C3—H3	125.5	O26—C27—H27C	108.9
C2—C3—H3	126.1	C28A—C27—H27D	108.6
C3—C4—N1	106.06 (19)	O26—C27—H27D	109.3
C3—C4—C5	132.3 (2)	H27C—C27—H27D	107.9
N1—C4—C5	121.57 (19)	C28—C27—H27A	108.7
C6—C5—C4	109.62 (17)	O26—C27—H27A	108.7
C6—C5—C21	109.06 (18)	C28—C27—H27B	108.4
C4—C5—C21	109.60 (18)	O26—C27—H27B	109.6
C6—C5—C22	110.87 (18)	H27A—C27—H27B	108.1
C4—C5—C22	108.90 (18)	C27—C28—H28A	110.4
C21—C5—C22	108.77 (17)	C27—C28—H28B	108.5
C7—C6—N2	106.9 (2)	H28A—C28—H28B	109.5
C7—C6—C5	130.9 (2)	C27—C28—H28C	109.5
N2—C6—C5	122.2 (2)	H28A—C28—H28C	109.5
C6—C7—C8	108.2 (2)	H28B—C28—H28C	109.5
C6—C7—H7	125.7	H28A—C28—H28E	100.7
C8—C7—H7	126.1	C27—C28A—H28D	110.5
C9—C8—C7	108.2 (2)	H28C—C28A—H28D	101.1
C9—C8—H8	125.5	C27—C28A—H28E	109.0
C7—C8—H8	126.3	H28D—C28A—H28E	109.5
C8—C9—N2	106.9 (2)	C27—C28A—H28F	108.9
C8—C9—C10	132.6 (2)	H28D—C28A—H28F	109.5
N2—C9—C10	120.3 (2)	H28E—C28A—H28F	109.5
C11—C10—C9	110.98 (19)	C15—C29—H29A	109.1
C11—C10—C23	110.0 (2)	C15—C29—H29B	110.3
C9—C10—C23	110.00 (18)	H29A—C29—H29B	109.5
C11—C10—C24	112.22 (18)	C15—C29—H29C	109.0
C9—C10—C24	105.9 (2)	H29A—C29—H29C	109.5
C23—C10—C24	107.6 (2)	H29B—C29—H29C	109.5
C12—C11—N3	106.0 (2)	C15—C30—H30A	109.5
C12—C11—C10	131.9 (2)	C15—C30—H30B	108.7
N3—C11—C10	122.0 (2)	H30A—C30—H30B	109.5
C11—C12—C13	108.9 (2)	C15—C30—H30C	110.3
C11—C12—H12	124.3	H30A—C30—H30C	109.5
C13—C12—H12	126.8	H30B—C30—H30C	109.5
C14—C13—C12	107.7 (2)	C20—C31—H31A	109.8
C14—C13—H13	125.9	C20—C31—H31B	109.2
C12—C13—H13	126.4	H31A—C31—H31B	109.4
C13—C14—N3	106.5 (2)	C20—C31—H31C	109.5
C13—C14—C15	133.7 (2)	H31A—C31—H31C	109.5
N3—C14—C15	119.8 (2)	H31B—C31—H31C	109.5
C14—C15—C16	109.75 (17)	O33—C32—O34	123.5 (2)
C14—C15—C29	109.79 (19)	O33—C32—C20	125.1 (2)
C16—C15—C29	109.15 (19)	O34—C32—C20	111.3 (2)
C14—C15—C30	109.4 (2)	C32—O34—C35	115.9 (2)
C16—C15—C30	110.53 (19)	C36A—C35—O34	108.3 (5)
C29—C15—C30	108.18 (18)	C36—C35—O34	109.9 (2)
C17—C16—N4	106.2 (2)	C36A—C35—H35C	109.8
C17—C16—C15	132.6 (2)	O34—C35—H35C	110.0
N4—C16—C15	121.2 (2)	C36A—C35—H35D	109.7
C16—C17—C18	108.3 (2)	O34—C35—H35D	110.5
C16—C17—H17	125.6	H35C—C35—H35D	108.6
C18—C17—H17	126.1	C36—C35—H35A	110.0
C19—C18—C17	108.0 (2)	O34—C35—H35A	109.8
C19—C18—H18	125.3	C36—C35—H35B	109.0
C17—C18—H18	126.7	O34—C35—H35B	109.5
C18—C19—N4	106.4 (2)	H35A—C35—H35B	108.6
C18—C19—C20	131.2 (2)	C35—C36—H36A	110.0
N4—C19—C20	122.40 (19)	C35—C36—H36B	108.9
C19—C20—C1	111.99 (17)	H36A—C36—H36B	109.5
C19—C20—C31	109.46 (18)	C35—C36—H36C	109.5
C1—C20—C31	109.13 (17)	H36A—C36—H36C	109.5
C19—C20—C32	109.68 (18)	H36B—C36—H36C	109.5
C1—C20—C32	104.12 (17)	C35—C36A—H36D	110.6
C31—C20—C32	112.4 (2)	H36C—C36A—H36D	101.6
C5—C21—H21A	109.3	C35—C36A—H36E	108.9
C5—C21—H21B	110.2	H36D—C36A—H36E	109.5
H21A—C21—H21B	109.5	C35—C36A—H36F	108.8
C5—C21—H21C	108.9	H36D—C36A—H36F	109.5
H21A—C21—H21C	109.5	H36E—C36A—H36F	109.5
H21B—C21—H21C	109.5
C4—N1—C1—C2	−0.6 (3)	N3—C14—C15—C16	46.3 (3)
C4—N1—C1—C20	−177.20 (18)	C13—C14—C15—C29	102.7 (3)
N1—C1—C2—C3	0.4 (3)	N3—C14—C15—C29	−73.7 (3)
C20—C1—C2—C3	176.5 (2)	C13—C14—C15—C30	−15.9 (3)
C1—C2—C3—C4	0.0 (3)	N3—C14—C15—C30	167.72 (19)
C2—C3—C4—N1	−0.4 (2)	C19—N4—C16—C17	−0.9 (3)
C2—C3—C4—C5	−176.6 (2)	C19—N4—C16—C15	−179.13 (19)
C1—N1—C4—C3	0.6 (3)	C14—C15—C16—C17	−112.8 (3)
C1—N1—C4—C5	177.35 (19)	C29—C15—C16—C17	7.6 (3)
C3—C4—C5—C6	−146.8 (2)	C30—C15—C16—C17	126.4 (3)
N1—C4—C5—C6	37.4 (3)	C14—C15—C16—N4	64.9 (3)
C3—C4—C5—C21	93.5 (3)	C29—C15—C16—N4	−174.8 (2)
N1—C4—C5—C21	−82.2 (2)	C30—C15—C16—N4	−55.9 (3)
C3—C4—C5—C22	−25.3 (3)	N4—C16—C17—C18	0.5 (3)
N1—C4—C5—C22	158.90 (19)	C15—C16—C17—C18	178.5 (2)
C9—N2—C6—C7	−0.1 (2)	C16—C17—C18—C19	0.0 (3)
C9—N2—C6—C5	−179.93 (19)	C17—C18—C19—N4	−0.5 (3)
C4—C5—C6—C7	−114.5 (3)	C17—C18—C19—C20	179.8 (2)
C21—C5—C6—C7	5.5 (3)	C16—N4—C19—C18	0.9 (3)
C22—C5—C6—C7	125.2 (3)	C16—N4—C19—C20	−179.41 (19)
C4—C5—C6—N2	65.3 (3)	C18—C19—C20—C1	120.4 (3)
C21—C5—C6—N2	−174.73 (19)	N4—C19—C20—C1	−59.2 (3)
C22—C5—C6—N2	−55.0 (3)	C18—C19—C20—C31	−0.7 (3)
N2—C6—C7—C8	−0.4 (2)	N4—C19—C20—C31	179.66 (19)
C5—C6—C7—C8	179.4 (2)	C18—C19—C20—C32	−124.5 (3)
C6—C7—C8—C9	0.8 (3)	N4—C19—C20—C32	55.9 (3)
C7—C8—C9—N2	−0.8 (3)	C2—C1—C20—C19	137.3 (2)
C7—C8—C9—C10	174.5 (2)	N1—C1—C20—C19	−47.1 (3)
C6—N2—C9—C8	0.6 (2)	C2—C1—C20—C31	−101.4 (3)
C6—N2—C9—C10	−175.44 (19)	N1—C1—C20—C31	74.3 (3)
C8—C9—C10—C11	125.4 (3)	C2—C1—C20—C32	18.9 (3)
N2—C9—C10—C11	−59.8 (3)	N1—C1—C20—C32	−165.5 (2)
C8—C9—C10—C23	−112.7 (3)	C11—C10—C24—O25	138.4 (3)
N2—C9—C10—C23	62.2 (3)	C9—C10—C24—O25	−100.4 (3)
C8—C9—C10—C24	3.3 (3)	C23—C10—C24—O25	17.2 (3)
N2—C9—C10—C24	178.14 (19)	C11—C10—C24—O26	−44.0 (3)
C14—N3—C11—C12	0.4 (2)	C9—C10—C24—O26	77.3 (2)
C14—N3—C11—C10	177.46 (19)	C23—C10—C24—O26	−165.12 (19)
C9—C10—C11—C12	126.1 (3)	O25—C24—O26—C27	−3.1 (4)
C23—C10—C11—C12	4.2 (3)	C10—C24—O26—C27	179.1 (2)
C24—C10—C11—C12	−115.5 (3)	C24—O26—C27—C28	88.2 (4)
C9—C10—C11—N3	−50.1 (3)	C24—O26—C27—C28A	165.5 (6)
C23—C10—C11—N3	−172.0 (2)	C19—C20—C32—O33	−37.8 (3)
C24—C10—C11—N3	68.3 (3)	C1—C20—C32—O33	82.2 (3)
N3—C11—C12—C13	−0.3 (3)	C31—C20—C32—O33	−159.8 (2)
C10—C11—C12—C13	−177.0 (2)	C19—C20—C32—O34	145.66 (19)
C11—C12—C13—C14	0.2 (3)	C1—C20—C32—O34	−94.3 (2)
C12—C13—C14—N3	0.1 (2)	C31—C20—C32—O34	23.6 (3)
C12—C13—C14—C15	−176.7 (2)	O33—C32—O34—C35	−5.7 (3)
C11—N3—C14—C13	−0.3 (2)	C20—C32—O34—C35	170.92 (19)
C11—N3—C14—C15	177.00 (18)	C32—O34—C35—C36A	−107.8 (8)
C13—C14—C15—C16	−137.3 (3)	C32—O34—C35—C36	−177.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O25i	0.86 (2)	2.37 (2)	3.211 (3)	167 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O25i	0.86 (2)	2.37 (2)	3.211 (3)	167 (2)

Symmetry code: (i) .