2,4,6,8-Tetra-kis(4-chloro-phen-yl)-3,7-diaza-bicyclo-[3.3.1]nonan-9-one O-benzyl-oxime acetone monosolvate.

In the title compound, C(38)H(31)Cl(4)N(3)O·C(3)H(6)O, the 3,7-diaza-bicycle exists in a chair-boat conformation. The 4-chloro-phenyl groups attached to the chair form are equatorially oriented at an angle of 18.15 (3)° with respect to each other, whereas the 4-chloro-phenyl groups attached to the boat form are oriented at an angle of 32.64 (3)°. In the crystal, mol-ecules are linked by N-H⋯π and C-H⋯O inter-actions.

Related literature

For the synthesis and stereochemistry of 3,7-diaza­bicyclo­[3.3.1]nonan-9-one derivatives, see: Parthiban et al. (2008 ▶). For the biological activity of 3,7-diaza­bicyclo­[3.3.1]nonan-9-one derivatives and related structures, see: Parthiban et al. (2009 ▶, 2010 ▶); Asakawa (1995 ▶); Jayaraman & Avila (1981 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶); Luger & Bülow (1983 ▶).

Experimental

Crystal data

C38H31Cl4N3O·C3H6O

M = 745.54

Monoclinic,

a = 14.9237 (5) Å

b = 10.5064 (3) Å

c = 24.6015 (7) Å

β = 93.116 (1)°

V = 3851.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 293 K

0.20 × 0.16 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.934, T max = 0.947

35931 measured reflections

7173 independent reflections

4263 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.188

S = 1.03

7173 reflections

475 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.89 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SIR92 (Altomare et al., 1993) ▶; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812016509/hb6689sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016509/hb6689Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812016509/hb6689Isup3.cml

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

C38H31Cl4N3O·C3H6O	F(000) = 1552
Mr = 745.54	Dx = 1.286 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6628 reflections
a = 14.9237 (5) Å	θ = 1.6–25.0°
b = 10.5064 (3) Å	µ = 0.35 mm−1
c = 24.6015 (7) Å	T = 293 K
β = 93.116 (1)°	Prism, colourless
V = 3851.7 (2) Å3	0.20 × 0.16 × 0.16 mm
Z = 4

Bruker APEXII CCD diffractometer	7173 independent reflections
Radiation source: fine-focus sealed tube	4263 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
ω and φ scan	θmax = 25.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −18→18
Tmin = 0.934, Tmax = 0.947	k = −12→8
35931 measured reflections	l = −29→29

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0699P)2 + 3.3824P] where P = (Fo2 + 2Fc2)/3
7173 reflections	(Δ/σ)max = 0.005
475 parameters	Δρmax = 0.89 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.2859 (2)	0.4608 (3)	0.27681 (13)	0.0522 (8)
C2	0.2691 (2)	0.3992 (3)	0.33290 (12)	0.0485 (7)
H2	0.2124	0.4308	0.3460	0.058*
C3	0.2670 (2)	0.2506 (3)	0.33063 (13)	0.0482 (7)
C4	0.4313 (2)	0.2457 (3)	0.34865 (14)	0.0484 (7)
C5	0.4330 (2)	0.3935 (3)	0.35421 (12)	0.0495 (7)
H5	0.4803	0.4192	0.3812	0.059*
C6	0.4467 (2)	0.4608 (3)	0.29906 (13)	0.0537 (8)
C7	0.3440 (2)	0.4355 (3)	0.37191 (12)	0.0505 (8)
C8	0.2128 (2)	0.4241 (3)	0.23443 (12)	0.0500 (8)
C9	0.2286 (2)	0.3441 (3)	0.19141 (13)	0.0576 (8)
H9	0.2865	0.3149	0.1868	0.069*
C10	0.1592 (2)	0.3064 (3)	0.15477 (14)	0.0627 (9)
H10	0.1704	0.2531	0.1257	0.075*
C11	0.0742 (2)	0.3494 (4)	0.16243 (14)	0.0602 (9)
C12	0.0572 (2)	0.4299 (4)	0.20424 (14)	0.0640 (9)
H12	−0.0008	0.4592	0.2085	0.077*
C13	0.1257 (2)	0.4674 (3)	0.23989 (14)	0.0603 (9)
H13	0.1139	0.5226	0.2682	0.072*
C14	0.1801 (2)	0.2023 (3)	0.35236 (13)	0.0499 (7)
C15	0.1040 (2)	0.1871 (3)	0.31863 (14)	0.0596 (9)
H15	0.1071	0.2026	0.2816	0.072*
C16	0.0231 (2)	0.1492 (4)	0.33852 (17)	0.0721 (10)
H16	−0.0278	0.1408	0.3153	0.086*
C17	0.0193 (2)	0.1245 (4)	0.39275 (18)	0.0756 (11)
C18	0.0929 (3)	0.1397 (4)	0.42751 (16)	0.0820 (12)
H18	0.0891	0.1241	0.4645	0.098*
C19	0.1732 (2)	0.1785 (4)	0.40740 (14)	0.0676 (10)
H19	0.2233	0.1889	0.4312	0.081*
C20	0.5042 (2)	0.1854 (3)	0.38518 (13)	0.0513 (8)
C21	0.4914 (2)	0.1632 (3)	0.43962 (14)	0.0597 (9)
H21	0.4358	0.1804	0.4534	0.072*
C22	0.5599 (3)	0.1161 (4)	0.47385 (15)	0.0685 (10)
H22	0.5511	0.1033	0.5106	0.082*
C23	0.6403 (2)	0.0886 (4)	0.45328 (17)	0.0688 (10)
C24	0.6552 (2)	0.1077 (4)	0.39992 (17)	0.0744 (11)
H24	0.7105	0.0878	0.3865	0.089*
C25	0.5870 (2)	0.1571 (4)	0.36575 (15)	0.0645 (9)
H25	0.5972	0.1715	0.3293	0.077*
C26	0.5374 (2)	0.4319 (3)	0.27753 (13)	0.0559 (8)
C27	0.6118 (3)	0.4936 (4)	0.29977 (17)	0.0784 (11)
H27	0.6051	0.5533	0.3271	0.094*
C28	0.6954 (3)	0.4685 (5)	0.2823 (2)	0.0986 (15)
H28	0.7454	0.5104	0.2978	0.118*
C29	0.7049 (3)	0.3807 (5)	0.2415 (2)	0.0927 (14)
C30	0.6326 (3)	0.3186 (5)	0.21902 (17)	0.0860 (13)
H30	0.6395	0.2587	0.1917	0.103*
C31	0.5497 (3)	0.3444 (4)	0.23664 (15)	0.0698 (10)
H31	0.5001	0.3021	0.2208	0.084*
C32	0.3717 (4)	0.5788 (5)	0.49734 (18)	0.1062 (16)
H32A	0.3446	0.6590	0.4858	0.127*
H32B	0.4242	0.5979	0.5208	0.127*
C33	0.3056 (4)	0.5049 (6)	0.52925 (17)	0.0944 (14)
C34	0.2425 (5)	0.5741 (8)	0.5549 (2)	0.136 (2)
H34	0.2418	0.6624	0.5522	0.163*
C35	0.1807 (6)	0.5133 (14)	0.5844 (4)	0.194 (5)
H35	0.1375	0.5612	0.6010	0.233*
C36	0.1804 (9)	0.3853 (15)	0.5902 (4)	0.198 (6)
H36	0.1380	0.3457	0.6107	0.238*
C37	0.2455 (9)	0.3128 (11)	0.5645 (4)	0.198 (5)
H37	0.2464	0.2245	0.5671	0.238*
C38	0.3095 (5)	0.3786 (6)	0.5345 (2)	0.1211 (19)
H38	0.3545	0.3334	0.5183	0.145*
C39	0.0817 (4)	0.6394 (6)	0.4002 (2)	0.1086 (17)
C40	0.0896 (7)	0.7529 (8)	0.4329 (3)	0.213 (4)
H40A	0.0921	0.8260	0.4096	0.320*
H40B	0.1433	0.7486	0.4561	0.320*
H40C	0.0385	0.7598	0.4548	0.320*
C41	0.0762 (4)	0.5122 (7)	0.4283 (3)	0.142 (2)
H41A	0.0714	0.4458	0.4015	0.213*
H41B	0.0245	0.5106	0.4498	0.213*
H41C	0.1293	0.4993	0.4514	0.213*
N1	0.37419 (18)	0.4222 (3)	0.26073 (11)	0.0534 (7)
N2	0.34337 (17)	0.2004 (3)	0.36383 (11)	0.0519 (7)
N3	0.3236 (2)	0.4941 (3)	0.41573 (12)	0.0745 (9)
O1	0.39933 (19)	0.5102 (3)	0.44974 (12)	0.0930 (9)
O2	0.0791 (4)	0.6448 (5)	0.35250 (17)	0.1589 (19)
Cl1	−0.01371 (7)	0.29806 (12)	0.11818 (4)	0.0871 (4)
Cl2	−0.08182 (8)	0.07631 (17)	0.41840 (6)	0.1228 (5)
Cl3	0.72648 (8)	0.03096 (14)	0.49745 (6)	0.1128 (5)
Cl4	0.81177 (10)	0.3490 (2)	0.21892 (8)	0.1549 (7)
H1	0.286 (2)	0.557 (3)	0.2824 (12)	0.060 (9)*
H1A	0.386 (2)	0.453 (3)	0.2293 (14)	0.060 (10)*
H2A	0.343 (2)	0.117 (3)	0.3623 (13)	0.059 (10)*
H3	0.2687 (19)	0.225 (3)	0.2914 (13)	0.050 (8)*
H4	0.4428 (18)	0.225 (3)	0.3110 (12)	0.042 (8)*
H6	0.4450 (19)	0.551 (3)	0.3059 (12)	0.049 (8)*

	U11	U22	U33	U12	U13	U23
C1	0.060 (2)	0.0453 (19)	0.0517 (19)	0.0018 (16)	0.0036 (15)	0.0040 (15)
C2	0.0522 (18)	0.0474 (18)	0.0463 (17)	0.0051 (15)	0.0063 (14)	0.0020 (14)
C3	0.0505 (18)	0.0478 (18)	0.0461 (18)	0.0029 (15)	0.0002 (14)	0.0030 (14)
C4	0.0481 (18)	0.0472 (18)	0.0501 (19)	0.0000 (15)	0.0030 (14)	−0.0009 (15)
C5	0.0553 (19)	0.0464 (18)	0.0464 (17)	−0.0041 (15)	−0.0011 (14)	−0.0015 (14)
C6	0.061 (2)	0.048 (2)	0.0523 (19)	−0.0040 (16)	0.0021 (16)	0.0021 (15)
C7	0.066 (2)	0.0440 (18)	0.0410 (17)	0.0014 (15)	0.0035 (15)	0.0010 (14)
C8	0.0557 (19)	0.0471 (18)	0.0470 (17)	0.0019 (15)	0.0010 (14)	0.0087 (14)
C9	0.057 (2)	0.063 (2)	0.0536 (19)	0.0061 (17)	0.0057 (16)	0.0036 (17)
C10	0.068 (2)	0.067 (2)	0.0526 (19)	0.0004 (19)	0.0006 (17)	−0.0006 (17)
C11	0.059 (2)	0.068 (2)	0.052 (2)	−0.0034 (18)	−0.0042 (16)	0.0173 (17)
C12	0.053 (2)	0.074 (2)	0.065 (2)	0.0100 (18)	0.0030 (17)	0.0140 (19)
C13	0.064 (2)	0.061 (2)	0.056 (2)	0.0126 (18)	0.0047 (17)	0.0060 (16)
C14	0.0512 (18)	0.0451 (17)	0.0533 (18)	0.0049 (14)	0.0008 (14)	0.0026 (14)
C15	0.059 (2)	0.063 (2)	0.0567 (19)	0.0010 (17)	−0.0018 (16)	−0.0045 (17)
C16	0.052 (2)	0.080 (3)	0.083 (3)	−0.0030 (19)	−0.0057 (19)	−0.008 (2)
C17	0.052 (2)	0.085 (3)	0.091 (3)	−0.004 (2)	0.011 (2)	0.010 (2)
C18	0.064 (2)	0.114 (4)	0.068 (2)	−0.002 (2)	0.010 (2)	0.029 (2)
C19	0.052 (2)	0.090 (3)	0.060 (2)	−0.0023 (19)	−0.0036 (16)	0.0198 (19)
C20	0.0519 (19)	0.0467 (18)	0.0549 (19)	−0.0043 (15)	−0.0009 (15)	0.0033 (15)
C21	0.056 (2)	0.062 (2)	0.061 (2)	0.0026 (17)	0.0039 (16)	0.0051 (17)
C22	0.069 (2)	0.073 (2)	0.062 (2)	−0.009 (2)	−0.0059 (19)	0.0179 (19)
C23	0.053 (2)	0.067 (2)	0.084 (3)	−0.0034 (18)	−0.0143 (19)	0.022 (2)
C24	0.049 (2)	0.087 (3)	0.086 (3)	0.0041 (19)	−0.0024 (19)	0.008 (2)
C25	0.054 (2)	0.077 (2)	0.063 (2)	0.0012 (18)	0.0042 (17)	0.0065 (18)
C26	0.058 (2)	0.058 (2)	0.0521 (19)	−0.0079 (17)	0.0031 (15)	0.0050 (16)
C27	0.063 (2)	0.082 (3)	0.091 (3)	−0.016 (2)	0.009 (2)	−0.016 (2)
C28	0.066 (3)	0.111 (4)	0.119 (4)	−0.026 (3)	0.008 (3)	−0.014 (3)
C29	0.069 (3)	0.112 (4)	0.100 (3)	−0.008 (3)	0.028 (2)	0.000 (3)
C30	0.080 (3)	0.101 (3)	0.080 (3)	−0.006 (3)	0.023 (2)	−0.022 (2)
C31	0.064 (2)	0.085 (3)	0.060 (2)	−0.010 (2)	0.0076 (18)	−0.010 (2)
C32	0.141 (5)	0.107 (4)	0.071 (3)	−0.015 (3)	0.002 (3)	−0.039 (3)
C33	0.118 (4)	0.111 (4)	0.053 (2)	0.005 (3)	−0.004 (3)	−0.016 (3)
C34	0.138 (5)	0.175 (7)	0.094 (4)	0.021 (5)	0.004 (4)	−0.004 (4)
C35	0.111 (6)	0.358 (17)	0.116 (6)	−0.002 (8)	0.022 (4)	0.019 (9)
C36	0.222 (12)	0.281 (17)	0.090 (6)	−0.079 (11)	−0.007 (6)	0.065 (8)
C37	0.296 (15)	0.192 (10)	0.102 (6)	−0.072 (10)	−0.037 (7)	0.038 (6)
C38	0.171 (6)	0.104 (5)	0.087 (4)	−0.008 (4)	−0.010 (4)	0.011 (3)
C39	0.116 (4)	0.124 (5)	0.086 (4)	0.021 (3)	0.013 (3)	−0.010 (3)
C40	0.314 (12)	0.155 (7)	0.170 (7)	0.005 (7)	−0.010 (7)	−0.062 (6)
C41	0.126 (5)	0.164 (6)	0.138 (5)	0.017 (4)	0.038 (4)	0.031 (5)
N1	0.0511 (16)	0.0626 (18)	0.0465 (16)	−0.0030 (13)	0.0039 (13)	0.0057 (14)
N2	0.0484 (16)	0.0447 (17)	0.0623 (17)	0.0005 (13)	0.0006 (12)	0.0088 (13)
N3	0.090 (2)	0.072 (2)	0.0593 (18)	−0.0117 (18)	−0.0146 (17)	0.0008 (16)
O1	0.0775 (19)	0.116 (2)	0.0848 (19)	−0.0107 (17)	0.0013 (15)	−0.0291 (17)
O2	0.234 (5)	0.156 (4)	0.087 (3)	0.043 (4)	0.015 (3)	0.002 (3)
Cl1	0.0746 (7)	0.1043 (8)	0.0801 (7)	−0.0127 (6)	−0.0181 (5)	0.0094 (6)
Cl2	0.0633 (7)	0.1634 (14)	0.1442 (12)	−0.0164 (8)	0.0286 (7)	0.0234 (10)
Cl3	0.0765 (8)	0.1344 (11)	0.1236 (10)	0.0078 (7)	−0.0308 (7)	0.0487 (8)
Cl4	0.0784 (9)	0.1845 (17)	0.2077 (18)	−0.0109 (10)	0.0618 (10)	−0.0301 (14)

C1—N1	1.454 (4)	C21—H21	0.9300
C1—C8	1.517 (4)	C22—C23	1.358 (5)
C1—C2	1.557 (4)	C22—H22	0.9300
C1—H1	1.02 (3)	C23—C24	1.358 (5)
C2—C7	1.482 (4)	C23—Cl3	1.746 (3)
C2—C3	1.562 (4)	C24—C25	1.385 (5)
C2—H2	0.9800	C24—H24	0.9300
C3—N2	1.465 (4)	C25—H25	0.9300
C3—C14	1.516 (4)	C26—C27	1.373 (5)
C3—H3	1.00 (3)	C26—C31	1.383 (5)
C4—N2	1.463 (4)	C27—C28	1.368 (6)
C4—C20	1.513 (4)	C27—H27	0.9300
C4—C5	1.558 (4)	C28—C29	1.375 (6)
C4—H4	0.98 (3)	C28—H28	0.9300
C5—C7	1.488 (4)	C29—C30	1.354 (6)
C5—C6	1.553 (4)	C29—Cl4	1.750 (4)
C5—H5	0.9800	C30—C31	1.360 (5)
C6—N1	1.454 (4)	C30—H30	0.9300
C6—C26	1.510 (5)	C31—H31	0.9300
C6—H6	0.97 (3)	C32—O1	1.454 (5)
C7—N3	1.292 (4)	C32—C33	1.508 (7)
C8—C9	1.382 (4)	C32—H32A	0.9700
C8—C13	1.391 (4)	C32—H32B	0.9700
C9—C10	1.393 (5)	C33—C38	1.334 (7)
C9—H9	0.9300	C33—C34	1.371 (8)
C10—C11	1.369 (5)	C34—C35	1.363 (11)
C10—H10	0.9300	C34—H34	0.9300
C11—C12	1.366 (5)	C35—C36	1.353 (15)
C11—Cl1	1.744 (4)	C35—H35	0.9300
C12—C13	1.369 (5)	C36—C37	1.410 (14)
C12—H12	0.9300	C36—H36	0.9300
C13—H13	0.9300	C37—C38	1.418 (11)
C14—C15	1.379 (4)	C37—H37	0.9300
C14—C19	1.386 (5)	C38—H38	0.9300
C15—C16	1.386 (5)	C39—O2	1.173 (6)
C15—H15	0.9300	C39—C40	1.441 (9)
C16—C17	1.363 (5)	C39—C41	1.509 (8)
C16—H16	0.9300	C40—H40A	0.9600
C17—C18	1.364 (5)	C40—H40B	0.9600
C17—Cl2	1.743 (4)	C40—H40C	0.9600
C18—C19	1.382 (5)	C41—H41A	0.9600
C18—H18	0.9300	C41—H41B	0.9600
C19—H19	0.9300	C41—H41C	0.9600
C20—C25	1.382 (5)	N1—H1A	0.86 (3)
C20—C21	1.383 (5)	N2—H2A	0.88 (4)
C21—C22	1.381 (5)	N3—O1	1.380 (4)
N1—C1—C8	111.7 (3)	C22—C21—H21	119.5
N1—C1—C2	108.5 (3)	C20—C21—H21	119.5
C8—C1—C2	111.0 (3)	C23—C22—C21	119.3 (3)
N1—C1—H1	108.4 (18)	C23—C22—H22	120.4
C8—C1—H1	110.1 (18)	C21—C22—H22	120.4
C2—C1—H1	106.9 (18)	C24—C23—C22	121.5 (3)
C7—C2—C1	108.3 (3)	C24—C23—Cl3	119.9 (3)
C7—C2—C3	107.1 (2)	C22—C23—Cl3	118.5 (3)
C1—C2—C3	112.8 (3)	C23—C24—C25	119.3 (4)
C7—C2—H2	109.5	C23—C24—H24	120.4
C1—C2—H2	109.5	C25—C24—H24	120.4
C3—C2—H2	109.5	C20—C25—C24	120.8 (3)
N2—C3—C14	109.7 (3)	C20—C25—H25	119.6
N2—C3—C2	109.1 (3)	C24—C25—H25	119.6
C14—C3—C2	109.8 (3)	C27—C26—C31	117.8 (3)
N2—C3—H3	112.2 (17)	C27—C26—C6	119.1 (3)
C14—C3—H3	108.4 (17)	C31—C26—C6	123.1 (3)
C2—C3—H3	107.7 (17)	C28—C27—C26	121.1 (4)
N2—C4—C20	109.8 (3)	C28—C27—H27	119.5
N2—C4—C5	108.3 (3)	C26—C27—H27	119.5
C20—C4—C5	110.9 (3)	C27—C28—C29	119.3 (4)
N2—C4—H4	112.1 (17)	C27—C28—H28	120.3
C20—C4—H4	108.2 (16)	C29—C28—H28	120.3
C5—C4—H4	107.6 (17)	C30—C29—C28	120.7 (4)
C7—C5—C6	106.4 (3)	C30—C29—Cl4	119.9 (4)
C7—C5—C4	108.1 (3)	C28—C29—Cl4	119.4 (4)
C6—C5—C4	112.3 (3)	C29—C30—C31	119.5 (4)
C7—C5—H5	110.0	C29—C30—H30	120.3
C6—C5—H5	110.0	C31—C30—H30	120.3
C4—C5—H5	110.0	C30—C31—C26	121.6 (4)
N1—C6—C26	111.5 (3)	C30—C31—H31	119.2
N1—C6—C5	108.1 (3)	C26—C31—H31	119.2
C26—C6—C5	112.2 (3)	O1—C32—C33	112.7 (4)
N1—C6—H6	111.3 (18)	O1—C32—H32A	109.0
C26—C6—H6	106.9 (18)	C33—C32—H32A	109.0
C5—C6—H6	106.8 (18)	O1—C32—H32B	109.0
N3—C7—C2	117.4 (3)	C33—C32—H32B	109.0
N3—C7—C5	129.8 (3)	H32A—C32—H32B	107.8
C2—C7—C5	112.8 (3)	C38—C33—C34	120.7 (6)
C9—C8—C13	118.1 (3)	C38—C33—C32	122.4 (6)
C9—C8—C1	122.4 (3)	C34—C33—C32	116.8 (6)
C13—C8—C1	119.4 (3)	C35—C34—C33	119.9 (9)
C8—C9—C10	121.2 (3)	C35—C34—H34	120.1
C8—C9—H9	119.4	C33—C34—H34	120.1
C10—C9—H9	119.4	C36—C35—C34	121.9 (11)
C11—C10—C9	118.6 (3)	C36—C35—H35	119.1
C11—C10—H10	120.7	C34—C35—H35	119.1
C9—C10—H10	120.7	C35—C36—C37	118.9 (12)
C12—C11—C10	121.3 (3)	C35—C36—H36	120.5
C12—C11—Cl1	119.8 (3)	C37—C36—H36	120.5
C10—C11—Cl1	118.9 (3)	C36—C37—C38	118.0 (11)
C11—C12—C13	119.8 (3)	C36—C37—H37	121.0
C11—C12—H12	120.1	C38—C37—H37	121.0
C13—C12—H12	120.1	C33—C38—C37	120.6 (8)
C12—C13—C8	120.9 (3)	C33—C38—H38	119.7
C12—C13—H13	119.5	C37—C38—H38	119.7
C8—C13—H13	119.5	O2—C39—C40	121.1 (7)
C15—C14—C19	117.6 (3)	O2—C39—C41	120.1 (6)
C15—C14—C3	121.2 (3)	C40—C39—C41	118.8 (6)
C19—C14—C3	121.1 (3)	C39—C40—H40A	109.5
C14—C15—C16	121.7 (3)	C39—C40—H40B	109.5
C14—C15—H15	119.1	H40A—C40—H40B	109.5
C16—C15—H15	119.1	C39—C40—H40C	109.5
C17—C16—C15	118.9 (3)	H40A—C40—H40C	109.5
C17—C16—H16	120.5	H40B—C40—H40C	109.5
C15—C16—H16	120.5	C39—C41—H41A	109.5
C16—C17—C18	121.1 (4)	C39—C41—H41B	109.5
C16—C17—Cl2	119.5 (3)	H41A—C41—H41B	109.5
C18—C17—Cl2	119.4 (3)	C39—C41—H41C	109.5
C17—C18—C19	119.6 (4)	H41A—C41—H41C	109.5
C17—C18—H18	120.2	H41B—C41—H41C	109.5
C19—C18—H18	120.2	C1—N1—C6	113.5 (3)
C18—C19—C14	121.0 (3)	C1—N1—H1A	112 (2)
C18—C19—H19	119.5	C6—N1—H1A	107 (2)
C14—C19—H19	119.5	C4—N2—C3	114.9 (3)
C25—C20—C21	118.2 (3)	C4—N2—H2A	109 (2)
C25—C20—C4	120.9 (3)	C3—N2—H2A	109 (2)
C21—C20—C4	120.8 (3)	C7—N3—O1	110.0 (3)
C22—C21—C20	120.9 (3)	N3—O1—C32	106.9 (3)
N1—C1—C2—C7	55.2 (3)	C3—C14—C19—C18	177.2 (4)
C8—C1—C2—C7	178.4 (3)	N2—C4—C20—C25	146.8 (3)
N1—C1—C2—C3	−63.2 (3)	C5—C4—C20—C25	−93.6 (4)
C8—C1—C2—C3	60.0 (3)	N2—C4—C20—C21	−36.6 (4)
C7—C2—C3—N2	−4.7 (3)	C5—C4—C20—C21	83.0 (4)
C1—C2—C3—N2	114.4 (3)	C25—C20—C21—C22	1.0 (5)
C7—C2—C3—C14	115.5 (3)	C4—C20—C21—C22	−175.6 (3)
C1—C2—C3—C14	−125.4 (3)	C20—C21—C22—C23	−1.5 (6)
N2—C4—C5—C7	−1.1 (3)	C21—C22—C23—C24	0.7 (6)
C20—C4—C5—C7	−121.6 (3)	C21—C22—C23—Cl3	179.2 (3)
N2—C4—C5—C6	−118.2 (3)	C22—C23—C24—C25	0.4 (6)
C20—C4—C5—C6	121.4 (3)	Cl3—C23—C24—C25	−178.0 (3)
C7—C5—C6—N1	−59.7 (3)	C21—C20—C25—C24	0.1 (5)
C4—C5—C6—N1	58.4 (3)	C4—C20—C25—C24	176.8 (3)
C7—C5—C6—C26	177.0 (3)	C23—C24—C25—C20	−0.9 (6)
C4—C5—C6—C26	−65.0 (4)	N1—C6—C26—C27	161.1 (3)
C1—C2—C7—N3	122.5 (3)	C5—C6—C26—C27	−77.5 (4)
C3—C2—C7—N3	−115.5 (3)	N1—C6—C26—C31	−19.9 (5)
C1—C2—C7—C5	−59.2 (3)	C5—C6—C26—C31	101.6 (4)
C3—C2—C7—C5	62.7 (3)	C31—C26—C27—C28	−0.5 (6)
C6—C5—C7—N3	−121.0 (4)	C6—C26—C27—C28	178.7 (4)
C4—C5—C7—N3	118.3 (4)	C26—C27—C28—C29	0.5 (7)
C6—C5—C7—C2	61.1 (3)	C27—C28—C29—C30	−0.5 (8)
C4—C5—C7—C2	−59.7 (3)	C27—C28—C29—Cl4	179.7 (4)
N1—C1—C8—C9	10.8 (4)	C28—C29—C30—C31	0.6 (8)
C2—C1—C8—C9	−110.5 (3)	Cl4—C29—C30—C31	−179.7 (4)
N1—C1—C8—C13	−172.1 (3)	C29—C30—C31—C26	−0.7 (7)
C2—C1—C8—C13	66.6 (4)	C27—C26—C31—C30	0.6 (6)
C13—C8—C9—C10	−0.7 (5)	C6—C26—C31—C30	−178.5 (4)
C1—C8—C9—C10	176.4 (3)	O1—C32—C33—C38	35.3 (7)
C8—C9—C10—C11	−0.6 (5)	O1—C32—C33—C34	−147.2 (5)
C9—C10—C11—C12	1.5 (5)	C38—C33—C34—C35	−2.5 (9)
C9—C10—C11—Cl1	−177.7 (3)	C32—C33—C34—C35	179.9 (6)
C10—C11—C12—C13	−1.0 (5)	C33—C34—C35—C36	1.2 (13)
Cl1—C11—C12—C13	178.2 (3)	C34—C35—C36—C37	−0.6 (16)
C11—C12—C13—C8	−0.4 (5)	C35—C36—C37—C38	1.1 (15)
C9—C8—C13—C12	1.2 (5)	C34—C33—C38—C37	3.2 (9)
C1—C8—C13—C12	−176.0 (3)	C32—C33—C38—C37	−179.4 (5)
N2—C3—C14—C15	−151.8 (3)	C36—C37—C38—C33	−2.5 (12)
C2—C3—C14—C15	88.3 (4)	C8—C1—N1—C6	177.3 (3)
N2—C3—C14—C19	31.7 (4)	C2—C1—N1—C6	−60.0 (3)
C2—C3—C14—C19	−88.1 (4)	C26—C6—N1—C1	−173.5 (3)
C19—C14—C15—C16	−0.1 (5)	C5—C6—N1—C1	62.8 (4)
C3—C14—C15—C16	−176.7 (3)	C20—C4—N2—C3	−179.0 (3)
C14—C15—C16—C17	−1.1 (6)	C5—C4—N2—C3	59.8 (3)
C15—C16—C17—C18	1.7 (6)	C14—C3—N2—C4	−176.9 (3)
C15—C16—C17—Cl2	−179.8 (3)	C2—C3—N2—C4	−56.6 (4)
C16—C17—C18—C19	−1.2 (7)	C2—C7—N3—O1	174.4 (3)
Cl2—C17—C18—C19	−179.7 (3)	C5—C7—N3—O1	−3.5 (5)
C17—C18—C19—C14	0.0 (7)	C7—N3—O1—C32	178.8 (3)
C15—C14—C19—C18	0.7 (6)	C33—C32—O1—N3	63.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2	0.93	2.52	3.441 (6)	172
N2—H2A···Cg3i	0.88 (3)	2.85 (3)	3.637 (3)	150 (3)

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2	0.93	2.52	3.441 (6)	172
N2—H2A⋯Cg3i	0.88 (3)	2.85 (3)	3.637 (3)	150 (3)

Symmetry code: (i) .