Sandine: a catharanthus-derived alkaloid

Gu, J.-M.; Hu, X.-R.

doi:10.1107/S1600536806035616

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Sandine: a catharanthus-derived alkaloid

J.-M. Gu and X.-R. Hu

Sandine, C₂₁H₂₂N₂O₃, which is a naturally occurring biologically active product derived from plants, is important as a possible starting material for the syntheses of valuable pharmaceuticals. The sandine framework consists of two five- and three six-membered condensed rings. One of the six-membered rings adopts a screw-boat conformation, one adopts an envelope conformation and the third is planar. Both five-membered rings have envelope structures. Molecules are linked into dimers by N—H

O hydrogen bonds. The asymmetric unit contains two molecules.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806035616/at2087sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806035616/at2087Isup2.hkl Contains datablock I

CCDC reference: 627295

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R factor = 0.064
wR factor = 0.173
Data-to-parameter ratio = 9.9

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT035_ALERT_1_A No _chemical_absolute_configuration info given .          ?

Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C4     -   C20     ..       8.00 su

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O11    -   C1      ..       5.99 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N11    -   C7      ..       5.48 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N31    -   C38     ..       6.51 su

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.48
           From the CIF: _reflns_number_total               4648
           Count of symmetry unique reflns         4666
           Completeness (_total/calc)             99.61%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C32    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C34    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C40    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C47    = .          S

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   9 ALERT level G = General alerts; check

   9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

Sandine top

Crystal data top

C₂₁H₂₂N₂O₃	F(000) = 1488.00
M_r = 350.42	D_x = 1.270 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2ac 2ab	Cell parameters from 22712 reflections
a = 13.377 (4) Å	θ = 3.0–27.5°
b = 14.905 (5) Å	µ = 0.09 mm⁻¹
c = 18.376 (4) Å	T = 298 K
V = 3663.9 (17) Å³	Chunk, yellow
Z = 8	0.45 × 0.42 × 0.23 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	R_int = 0.078
Detector resolution: 10.00 pixels mm^-1	θ_max = 27.5°
ω scans	h = −17→17
34182 measured reflections	k = −19→19
4648 independent reflections	l = −22→23
3098 reflections with F² > 2σ(F²)

Refinement top

Refinement on F²	w = 1/[σ²(F_o²) + (0.112P)²] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.064	(Δ/σ)_max = 0.0001
wR(F²) = 0.173	Δρ_max = 0.35 e Å⁻³
S = 1.00	Δρ_min = −0.28 e Å⁻³
4648 reflections	Extinction correction: SHELXL97 (Sheldrick, 1997)
471 parameters	Extinction coefficient: 0.03186 (11)
H-atom parameters constrained

Special details top

Refinement. Refinement using all reflections. The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O11	0.90885 (12)	0.24383 (12)	0.59007 (10)	0.0655 (4)
O12	0.78633 (19)	0.06710 (16)	0.49829 (10)	0.0929 (6)
O13	0.68803 (16)	0.17770 (16)	0.53845 (9)	0.0854 (6)
O31	0.81427 (13)	0.46225 (12)	0.64934 (8)	0.0661 (4)
O32	0.57661 (17)	0.54803 (18)	0.63321 (12)	0.1020 (7)
O33	0.60056 (13)	0.43181 (14)	0.55922 (11)	0.0774 (5)
N11	0.7619 (2)	−0.06079 (18)	0.71482 (17)	0.0916 (7)
N12	0.79015 (14)	0.27466 (13)	0.67181 (10)	0.0561 (4)
N31	0.70058 (17)	0.71565 (14)	0.45105 (12)	0.0673 (5)
N32	0.83565 (14)	0.41285 (13)	0.53558 (10)	0.0579 (5)
C1	0.83784 (18)	0.21882 (17)	0.62819 (12)	0.0524 (5)
C2	0.80227 (17)	0.12085 (16)	0.62263 (11)	0.0526 (5)
C3	0.89208 (19)	0.05790 (19)	0.63431 (12)	0.0629 (6)
C4	0.89675 (19)	0.04453 (19)	0.71708 (13)	0.0628 (6)
C5	0.9544 (2)	−0.0358 (2)	0.74468 (19)	0.0927 (10)
C6	0.9133 (3)	−0.1071 (2)	0.7711 (2)	0.1076 (12)
C7	0.8064 (3)	−0.1246 (2)	0.7650 (2)	0.0976 (15)
C8	0.6593 (2)	−0.0624 (2)	0.7000 (2)	0.0964 (10)
C9	0.6482 (2)	0.0193 (2)	0.65154 (16)	0.0748 (8)
C10	0.72288 (17)	0.09020 (17)	0.68127 (12)	0.0549 (5)
C11	0.67009 (17)	0.16748 (18)	0.71872 (11)	0.0542 (5)
C12	0.58646 (19)	0.1528 (2)	0.76245 (13)	0.0711 (7)
C13	0.5390 (2)	0.2229 (2)	0.79718 (14)	0.0811 (9)
C14	0.5729 (2)	0.3090 (2)	0.78901 (14)	0.0771 (8)
C15	0.6554 (2)	0.32555 (19)	0.74680 (12)	0.0635 (6)
C16	0.70402 (18)	0.25496 (17)	0.71283 (11)	0.0523 (5)
C17	0.7862 (2)	0.03267 (19)	0.73510 (13)	0.0656 (6)
C18	0.7600 (2)	0.1170 (2)	0.54608 (12)	0.0676 (7)
C19	0.6388 (2)	0.1833 (3)	0.46810 (17)	0.1040 (15)
C20	0.9375 (2)	0.1249 (2)	0.75830 (18)	0.0878 (9)
C21	1.0204 (2)	0.1644 (3)	0.7498 (2)	0.1030 (15)
C31	0.79682 (18)	0.47058 (16)	0.58364 (11)	0.0503 (5)
C32	0.72498 (17)	0.54267 (16)	0.55790 (11)	0.0519 (5)
C33	0.7565 (2)	0.63293 (17)	0.58999 (12)	0.0650 (6)
C34	0.83078 (19)	0.67144 (17)	0.53514 (12)	0.0585 (6)
C35	0.8444 (2)	0.7731 (2)	0.54043 (18)	0.0810 (8)
C36	0.8085 (2)	0.8305 (2)	0.49346 (19)	0.0879 (9)
C37	0.7409 (2)	0.8030 (2)	0.43382 (18)	0.0825 (8)
C38	0.6274 (2)	0.6727 (2)	0.40481 (17)	0.0791 (8)
C39	0.61335 (19)	0.5849 (2)	0.44491 (14)	0.0687 (7)
C40	0.71969 (17)	0.55947 (16)	0.47318 (11)	0.0508 (5)
C41	0.76431 (18)	0.48351 (16)	0.42866 (11)	0.0518 (5)
C42	0.7547 (2)	0.4809 (2)	0.35308 (12)	0.0746 (8)
C43	0.7978 (2)	0.4142 (2)	0.31197 (14)	0.0879 (9)
C44	0.8517 (2)	0.3479 (2)	0.34468 (16)	0.0901 (9)
C45	0.8617 (2)	0.3466 (2)	0.41907 (14)	0.0761 (8)
C46	0.81911 (18)	0.41503 (17)	0.46025 (12)	0.0561 (6)
C47	0.77795 (17)	0.64903 (16)	0.46355 (12)	0.0534 (5)
C48	0.6250 (2)	0.5102 (2)	0.58846 (13)	0.0635 (6)
C49	0.5072 (2)	0.3922 (2)	0.5819 (2)	0.1059 (12)
C50	0.9304 (2)	0.6268 (2)	0.54342 (16)	0.0742 (7)
C51	0.9910 (2)	0.6001 (3)	0.4959 (2)	0.1080 (18)
H5	1.0238	−0.0337	0.7425	0.111*
H6	0.9534	−0.1489	0.7948	0.129*
H12	0.5623	0.0947	0.7683	0.085*
H13	0.4836	0.2116	0.8264	0.097*
H14	0.5400	0.3561	0.8120	0.093*
H15	0.6787	0.3839	0.7410	0.076*
H17	0.7711	0.0459	0.7862	0.079*
H20	0.8963	0.1481	0.7944	0.105*
H31	0.8815	0.0011	0.6097	0.075*
H32	0.9532	0.0853	0.6165	0.075*
H35	0.8805	0.7956	0.5796	0.097*
H36	0.8261	0.8906	0.4977	0.105*
H42	0.7182	0.5255	0.3298	0.089*
H43	0.7901	0.4143	0.2617	0.106*
H44	0.8818	0.3036	0.3166	0.108*
H45	0.8966	0.3004	0.4417	0.091*
H47	0.8251	0.6460	0.4228	0.064*
H50	0.9506	0.6173	0.5912	0.089*
H71	0.7960	−0.1851	0.7470	0.117*
H72	0.7754	−0.1184	0.8125	0.117*
H81	0.6201	−0.0566	0.7441	0.116*
H82	0.6402	−0.1169	0.6747	0.116*
H91	0.5804	0.0422	0.6539	0.090*
H92	0.6644	0.0042	0.6016	0.090*
H121	0.8139	0.3281	0.6755	0.067*
H191	0.5925	0.2325	0.4683	0.125*
H192	0.6034	0.1285	0.4588	0.125*
H193	0.6879	0.1926	0.4308	0.125*
H211	1.0650	0.1445	0.7145	0.124*
H212	1.0367	0.2134	0.7788	0.124*
H321	0.8737	0.3711	0.5522	0.069*
H331	0.6992	0.6723	0.5952	0.078*
H332	0.7881	0.6247	0.6370	0.078*
H371	0.6869	0.8461	0.4291	0.099*
H372	0.7779	0.8001	0.3885	0.099*
H381	0.6528	0.6633	0.3560	0.095*
H382	0.5657	0.7068	0.4025	0.095*
H391	0.5881	0.5390	0.4123	0.082*
H392	0.5674	0.5924	0.4853	0.082*
H491	0.4537	0.4339	0.5734	0.127*
H492	0.5104	0.3781	0.6328	0.127*
H493	0.4955	0.3383	0.5546	0.127*
H511	0.9761	0.6072	0.4468	0.130*
H512	1.0508	0.5732	0.5098	0.130*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O11	0.0582 (9)	0.0650 (11)	0.0733 (10)	0.0040 (9)	0.0190 (8)	0.0165 (8)
O12	0.1174 (17)	0.1003 (16)	0.0609 (10)	0.0110 (14)	0.0044 (11)	−0.0233 (10)
O13	0.0803 (12)	0.1186 (17)	0.0573 (10)	0.0253 (13)	−0.0147 (9)	−0.0085 (10)
O31	0.0835 (12)	0.0630 (11)	0.0517 (9)	−0.0021 (10)	−0.0055 (8)	0.0026 (7)
O32	0.0831 (13)	0.1182 (19)	0.1046 (16)	0.0072 (14)	0.0407 (12)	−0.0199 (14)
O33	0.0672 (11)	0.0788 (15)	0.0862 (12)	−0.0238 (10)	0.0148 (9)	−0.0052 (10)
N11	0.0859 (18)	0.0659 (16)	0.123 (2)	−0.0093 (14)	0.0030 (15)	0.0148 (14)
N12	0.0575 (11)	0.0521 (12)	0.0587 (10)	−0.0028 (10)	0.0075 (9)	−0.0007 (8)
N31	0.0615 (12)	0.0593 (14)	0.0812 (14)	0.0098 (11)	−0.0060 (11)	0.0094 (10)
N32	0.0641 (12)	0.0569 (12)	0.0527 (10)	0.0106 (10)	0.0018 (9)	0.0024 (9)
C1	0.0516 (12)	0.0590 (15)	0.0465 (11)	0.0092 (12)	0.0003 (10)	0.0049 (10)
C2	0.0530 (12)	0.0549 (15)	0.0499 (11)	0.0021 (11)	0.0039 (10)	−0.0022 (9)
C3	0.0639 (15)	0.0541 (15)	0.0707 (15)	0.0092 (12)	0.0114 (12)	0.0039 (11)
C4	0.0612 (15)	0.0585 (16)	0.0687 (14)	0.0065 (13)	0.0003 (12)	0.0066 (12)
C5	0.088 (2)	0.082 (2)	0.108 (2)	0.026 (2)	0.0045 (18)	0.0232 (19)
C6	0.105 (2)	0.083 (2)	0.135 (3)	0.016 (2)	0.001 (2)	0.034 (2)
C7	0.098 (3)	0.071 (2)	0.123 (3)	0.004 (2)	−0.004 (3)	0.028 (2)
C8	0.090 (2)	0.075 (2)	0.124 (2)	−0.0208 (19)	0.016 (2)	−0.0004 (19)
C9	0.0596 (15)	0.080 (2)	0.0852 (17)	−0.0174 (15)	0.0057 (13)	−0.0128 (15)
C10	0.0491 (12)	0.0609 (15)	0.0546 (12)	−0.0057 (12)	0.0023 (10)	−0.0030 (10)
C11	0.0443 (12)	0.0730 (17)	0.0453 (11)	−0.0029 (12)	−0.0008 (9)	−0.0038 (10)
C12	0.0544 (14)	0.095 (2)	0.0640 (14)	−0.0092 (15)	0.0096 (12)	−0.0089 (14)
C13	0.0521 (15)	0.124 (3)	0.0673 (17)	0.0037 (18)	0.0134 (12)	−0.0121 (17)
C14	0.0678 (17)	0.099 (2)	0.0645 (16)	0.0243 (18)	0.0008 (14)	−0.0161 (15)
C15	0.0642 (15)	0.0699 (17)	0.0562 (13)	0.0138 (14)	−0.0009 (11)	−0.0088 (12)
C16	0.0493 (12)	0.0653 (16)	0.0425 (11)	0.0056 (12)	−0.0011 (10)	−0.0027 (9)
C17	0.0695 (16)	0.0642 (17)	0.0631 (13)	−0.0011 (14)	0.0030 (12)	0.0090 (11)
C18	0.0688 (16)	0.078 (2)	0.0560 (14)	0.0013 (15)	0.0051 (12)	−0.0049 (12)
C19	0.103 (2)	0.139 (4)	0.0706 (19)	0.023 (2)	−0.037 (2)	−0.002 (2)
C20	0.073 (2)	0.096 (2)	0.095 (2)	0.0015 (19)	−0.0223 (16)	0.0060 (18)
C21	0.096 (3)	0.103 (3)	0.110 (3)	−0.027 (2)	−0.020 (2)	0.004 (2)
C31	0.0570 (13)	0.0485 (13)	0.0455 (11)	−0.0082 (11)	0.0019 (10)	−0.0008 (9)
C32	0.0544 (12)	0.0510 (14)	0.0504 (11)	−0.0016 (11)	0.0038 (10)	−0.0046 (9)
C33	0.0807 (17)	0.0553 (15)	0.0590 (12)	0.0006 (14)	0.0042 (13)	−0.0052 (11)
C34	0.0613 (14)	0.0455 (14)	0.0689 (14)	−0.0002 (12)	−0.0022 (12)	−0.0054 (11)
C35	0.089 (2)	0.0562 (19)	0.098 (2)	−0.0083 (16)	−0.0004 (17)	−0.0181 (16)
C36	0.108 (2)	0.0455 (17)	0.110 (2)	−0.0043 (17)	0.006 (2)	−0.0004 (16)
C37	0.091 (2)	0.0538 (17)	0.103 (2)	0.0106 (16)	0.0128 (18)	0.0127 (14)
C38	0.0619 (15)	0.082 (2)	0.0931 (19)	0.0129 (15)	−0.0093 (15)	0.0216 (16)
C39	0.0531 (14)	0.080 (2)	0.0727 (16)	−0.0027 (14)	−0.0050 (12)	0.0063 (13)
C40	0.0475 (12)	0.0538 (14)	0.0512 (11)	−0.0015 (11)	0.0011 (10)	0.0032 (9)
C41	0.0561 (13)	0.0513 (14)	0.0480 (11)	−0.0079 (11)	−0.0007 (10)	−0.0019 (9)
C42	0.099 (2)	0.0737 (19)	0.0513 (13)	−0.0127 (17)	−0.0037 (13)	−0.0006 (12)
C43	0.127 (2)	0.085 (2)	0.0514 (14)	−0.012 (2)	0.0111 (17)	−0.0182 (14)
C44	0.118 (2)	0.078 (2)	0.0733 (18)	−0.004 (2)	0.0262 (18)	−0.0227 (16)
C45	0.093 (2)	0.0649 (19)	0.0704 (16)	0.0070 (16)	0.0211 (15)	−0.0089 (13)
C46	0.0639 (14)	0.0559 (15)	0.0484 (12)	−0.0052 (12)	0.0091 (11)	−0.0046 (10)
C47	0.0506 (12)	0.0504 (14)	0.0591 (12)	0.0032 (11)	0.0016 (10)	−0.0006 (10)
C48	0.0603 (15)	0.0714 (19)	0.0589 (13)	0.0043 (14)	0.0103 (12)	0.0017 (12)
C49	0.077 (2)	0.130 (3)	0.111 (2)	−0.039 (2)	0.0079 (18)	0.003 (2)
C50	0.0650 (16)	0.0696 (19)	0.0879 (19)	−0.0070 (15)	−0.0162 (15)	−0.0059 (15)
C51	0.084 (2)	0.146 (5)	0.094 (2)	0.025 (3)	−0.011 (2)	−0.026 (3)

Geometric parameters (Å, º) top

O11—C1	1.238 (2)	C40—C47	1.556 (3)
O12—C18	1.203 (3)	C41—C42	1.395 (3)
O13—C18	1.329 (3)	C41—C46	1.384 (3)
O13—C19	1.453 (3)	C42—C43	1.375 (4)
O31—C31	1.236 (2)	C43—C44	1.362 (4)
O32—C48	1.188 (3)	C44—C45	1.374 (4)
O33—C48	1.327 (3)	C45—C46	1.393 (3)
O33—C49	1.443 (4)	C50—C51	1.256 (4)
N11—C7	1.452 (5)	N12—H121	0.860
N11—C8	1.399 (4)	N32—H321	0.860
N11—C17	1.478 (3)	C3—H31	0.970
N12—C1	1.320 (3)	C3—H32	0.970
N12—C16	1.408 (3)	C5—H5	0.930
N31—C37	1.445 (3)	C6—H6	0.930
N31—C38	1.446 (3)	C7—H71	0.970
N31—C47	1.453 (3)	C7—H72	0.970
N32—C31	1.338 (2)	C8—H81	0.970
N32—C46	1.402 (2)	C8—H82	0.970
C1—C2	1.539 (3)	C9—H91	0.970
C2—C3	1.539 (3)	C9—H92	0.970
C2—C10	1.580 (3)	C12—H12	0.930
C2—C18	1.517 (3)	C13—H13	0.930
C3—C4	1.535 (3)	C14—H14	0.930
C4—C5	1.512 (4)	C15—H15	0.930
C4—C17	1.525 (3)	C17—H17	0.980
C4—C20	1.519 (4)	C19—H191	0.960
C5—C6	1.291 (5)	C19—H192	0.960
C6—C7	1.458 (6)	C19—H193	0.960
C8—C9	1.517 (4)	C20—H20	0.930
C9—C10	1.553 (3)	C21—H211	0.930
C10—C11	1.516 (3)	C21—H212	0.930
C10—C17	1.560 (3)	C33—H331	0.970
C11—C12	1.395 (3)	C33—H332	0.970
C11—C16	1.385 (3)	C35—H35	0.930
C12—C13	1.379 (4)	C36—H36	0.930
C13—C14	1.368 (5)	C37—H371	0.970
C14—C15	1.372 (3)	C37—H372	0.970
C15—C16	1.385 (3)	C38—H381	0.970
C20—C21	1.265 (5)	C38—H382	0.970
C31—C32	1.517 (3)	C39—H391	0.970
C32—C33	1.528 (3)	C39—H392	0.970
C32—C40	1.578 (2)	C42—H42	0.930
C32—C48	1.530 (3)	C43—H43	0.930
C33—C34	1.527 (3)	C44—H44	0.930
C34—C35	1.529 (3)	C45—H45	0.930
C34—C47	1.530 (3)	C47—H47	0.980
C34—C50	1.498 (3)	C49—H491	0.960
C35—C36	1.306 (4)	C49—H492	0.960
C36—C37	1.478 (4)	C49—H493	0.960
C38—C39	1.513 (4)	C50—H50	0.930
C39—C40	1.561 (3)	C51—H511	0.930
C40—C41	1.519 (3)	C51—H512	0.930

O11···N32	2.882 (2)	H42···H211^vi	3.358
O11···C19ⁱ	3.433 (4)	H43···O31^xiii	3.098
O11···C45	3.552 (3)	H43···O32^xiii	3.011
O12···C36ⁱⁱ	3.540 (3)	H43···C33^xiii	3.292
O12···C49ⁱ	3.357 (4)	H43···C48^xiii	3.562
O31···N12	2.845 (2)	H43···H13ⁱ	3.583
O31···C15	3.446 (3)	H43···H15^xiii	3.061
O32···C12ⁱⁱⁱ	3.297 (3)	H43···H211^vi	3.166
O32···C13ⁱⁱⁱ	3.290 (4)	H43···H331^xiii	3.323
N12···O31	2.845 (2)	H43···H332^xiii	2.584
N12···N32	3.298 (2)	H44···C12ⁱ	3.167
N12···C31	3.341 (3)	H44···C13ⁱ	2.992
N32···O11	2.882 (2)	H44···H12ⁱ	3.250
N32···N12	3.298 (2)	H44···H13ⁱ	2.968
N32···C1	3.356 (3)	H44···H71^ix	3.226
C1···N32	3.356 (3)	H44···H72^ix	3.471
C6···C21^iv	3.540 (6)	H44···H91ⁱ	3.554
C12···O32^v	3.297 (3)	H44···H492ⁱ	3.340
C13···O32^v	3.290 (4)	H44···H493ⁱ	3.519
C15···O31	3.446 (3)	H45···O11	2.858
C19···O11^vi	3.433 (4)	H45···C49ⁱ	3.258
C21···C6^vii	3.540 (6)	H45···H191ⁱ	3.138
C31···N12	3.341 (3)	H45···H192ⁱ	3.481
C36···O12^viii	3.540 (3)	H45···H193	3.227
C45···O11	3.552 (3)	H45···H491ⁱ	3.584
C49···O12^vi	3.357 (4)	H45···H492ⁱ	3.357
O11···H6^vii	3.229	H45···H493ⁱ	2.455
O11···H45	2.858	H47···C13^xiii	3.529
O11···H191ⁱ	2.704	H47···C14^xiii	2.891
O11···H192ⁱ	3.347	H47···C15^xiii	3.272
O11···H321	2.075	H47···H14^xiii	2.720
O11···H493ⁱ	3.148	H47···H15^xiii	3.371
O12···H36ⁱⁱ	2.683	H50···C20^vii	3.146
O12···H72^ix	3.596	H50···C21^vii	3.029
O12···H491ⁱ	2.598	H50···H20^vii	2.970
O12···H493ⁱ	3.280	H50···H211^vii	3.598
O13···H493	3.529	H50···H212^vii	2.789
O31···H5^vii	2.940	H50···H371^xii	3.230
O31···H15	2.737	H50···H382^xii	3.042
O31···H42^x	3.350	H71···C21^iv	3.327
O31···H43^x	3.098	H71···H35ⁱⁱ	3.290
O31···H121	2.057	H71···H44^xi	3.226
O32···H12ⁱⁱⁱ	2.686	H71···H193^xi	3.386
O32···H13ⁱⁱⁱ	2.673	H71···H211^iv	3.227
O32···H15	3.431	H71···H212^iv	2.744
O32···H43^x	3.011	H71···H332ⁱⁱ	3.484
O33···H15	3.573	H72···O12^xi	3.596
O33···H191	3.410	H72···C19^xi	3.230
N12···H321	2.855	H72···H44^xi	3.471
N12···H381^x	3.590	H72···H192^xi	3.143
N32···H121	2.880	H72···H193^xi	2.488
C1···H321	2.708	H81···C14^v	3.324
C3···H391ⁱ	3.114	H81···H14^v	2.711
C5···H391ⁱ	3.394	H81···H491^v	3.498
C6···H192^xi	3.471	H81···H492^v	3.017
C6···H193^xi	3.474	H82···C13^v	3.422
C6···H212^iv	2.906	H82···C14^v	3.129
C7···H193^xi	3.212	H82···H13^v	3.045
C7···H212^iv	3.299	H82···H14^v	2.457
C8···H14^v	2.938	H82···H331ⁱⁱ	3.553
C9···H14^v	3.565	H82···H511^vi	3.135
C9···H511^vi	3.482	H91···C44^vi	3.469
C9···H512^vi	3.520	H91···H14^v	3.268
C11···H372^x	3.232	H91···H44^vi	3.554
C12···H44^vi	3.167	H91···H511^vi	3.214
C12···H372^x	3.025	H91···H512^vi	3.488
C13···H44^vi	2.992	H92···C51^vi	3.317
C13···H47^x	3.529	H92···H36ⁱⁱ	3.345
C13···H82ⁱⁱⁱ	3.422	H92···H511^vi	3.145
C13···H372^x	2.988	H92···H512^vi	2.798
C14···H47^x	2.891	H121···O31	2.057
C14···H81ⁱⁱⁱ	3.324	H121···N32	2.880
C14···H82ⁱⁱⁱ	3.129	H121···C31	2.723
C14···H372^x	3.157	H121···H5^vii	3.350
C14···H492	3.162	H121···H6^vii	3.178
C14···H511^x	3.225	H121···H321	2.488
C15···H42^x	3.180	H121···H381^x	3.348
C15···H47^x	3.272	H191···O11^vi	2.704
C15···H372^x	3.329	H191···O33	3.410
C15···H381^x	3.260	H191···C49	3.366
C15···H492	2.960	H191···H6^ix	3.477
C16···H372^x	3.339	H191···H45^vi	3.138
C16···H381^x	3.474	H191···H321^vi	3.331
C16···H492	3.498	H191···H493	2.587
C18···H36ⁱⁱ	3.599	H192···O11^vi	3.347
C18···H491ⁱ	3.480	H192···C6^ix	3.471
C19···H6^ix	3.453	H192···H6^ix	3.122
C19···H72^ix	3.230	H192···H45^vi	3.481
C19···H493	3.398	H192···H72^ix	3.143
C20···H50^iv	3.146	H192···H321^vi	3.079
C20···H371^x	3.580	H192···H512^vi	3.141
C21···H6^vii	2.923	H193···C6^ix	3.474
C21···H50^iv	3.029	H193···C7^ix	3.212
C21···H71^vii	3.327	H193···C44	3.558
C21···H332^iv	3.352	H193···C45	3.274
C21···H382^x	3.589	H193···H6^ix	3.200
C31···H15	3.540	H193···H45	3.227
C31···H121	2.723	H193···H71^ix	3.386
C33···H43^x	3.292	H193···H72^ix	2.488
C35···H382^xii	3.155	H211···C42ⁱ	3.387
C36···H31^viii	3.462	H211···C43ⁱ	3.271
C37···H17^xiii	3.530	H211···H6^vii	3.095
C37···H20^xiii	3.234	H211···H42ⁱ	3.358
C37···H512^xiv	3.308	H211···H43ⁱ	3.166
C38···H20^xiii	3.369	H211···H50^iv	3.598
C38···H35^xiv	3.348	H211···H71^vii	3.227
C39···H31^vi	3.502	H211···H332^iv	3.374
C39···H32^vi	3.507	H212···C6^vii	2.906
C42···H15^xiii	3.016	H212···C7^vii	3.299
C42···H211^vi	3.387	H212···C50^iv	3.540
C43···H15^xiii	3.295	H212···H6^vii	2.463
C43···H211^vi	3.271	H212···H35^iv	3.081
C43···H332^xiii	3.463	H212···H50^iv	2.789
C44···H91ⁱ	3.469	H212···H71^vii	2.744
C44···H193	3.558	H212···H332^iv	3.103
C45···H193	3.274	H212···H381^x	3.437
C45···H493ⁱ	3.321	H212···H382^x	2.908
C48···H15	3.453	H321···O11	2.075
C48···H43^x	3.562	H321···N12	2.855
C49···H45^vi	3.258	H321···C1	2.708
C49···H191	3.366	H321···H121	2.488
C50···H212^vii	3.540	H321···H191ⁱ	3.331
C50···H371^xii	3.492	H321···H192ⁱ	3.079
C50···H382^xii	3.227	H331···H13ⁱⁱⁱ	2.899
C51···H14^xiii	3.467	H331···H43^x	3.323
C51···H92ⁱ	3.317	H331···H82^viii	3.553
C51···H371^xii	3.068	H332···C21^vii	3.352
C51···H382^xii	3.573	H332···C43^x	3.463
H5···O31^iv	2.940	H332···H43^x	2.584
H5···H42ⁱ	2.922	H332···H71^viii	3.484
H5···H121^iv	3.350	H332···H211^vii	3.374
H5···H381ⁱ	3.160	H332···H212^vii	3.103
H5···H391ⁱ	2.972	H371···C20^xiii	3.580
H6···O11^iv	3.229	H371···C50^xiv	3.492
H6···C19^xi	3.453	H371···C51^xiv	3.068
H6···C21^iv	2.923	H371···H17^xiii	3.132
H6···H121^iv	3.178	H371···H20^xiii	2.715
H6···H191^xi	3.477	H371···H50^xiv	3.230
H6···H192^xi	3.122	H371···H512^xiv	2.454
H6···H193^xi	3.200	H372···C11^xiii	3.232
H6···H211^iv	3.095	H372···C12^xiii	3.025
H6···H212^iv	2.463	H372···C13^xiii	2.988
H12···O32^v	2.686	H372···C14^xiii	3.157
H12···H44^vi	3.250	H372···C15^xiii	3.329
H12···H372^x	3.450	H372···C16^xiii	3.339
H13···O32^v	2.673	H372···H12^xiii	3.450
H13···H43^vi	3.583	H372···H13^xiii	3.393
H13···H44^vi	2.968	H372···H17^xiii	3.039
H13···H82ⁱⁱⁱ	3.045	H372···H20^xiii	3.002
H13···H331^v	2.899	H381···N12^xiii	3.590
H13···H372^x	3.393	H381···C15^xiii	3.260
H13···H511^x	3.533	H381···C16^xiii	3.474
H14···C8ⁱⁱⁱ	2.938	H381···H5^vi	3.160
H14···C9ⁱⁱⁱ	3.565	H381···H15^xiii	3.168
H14···C51^x	3.467	H381···H20^xiii	3.100
H14···H47^x	2.720	H381···H121^xiii	3.348
H14···H81ⁱⁱⁱ	2.711	H381···H212^xiii	3.437
H14···H82ⁱⁱⁱ	2.457	H382···C21^xiii	3.589
H14···H91ⁱⁱⁱ	3.268	H382···C35^xiv	3.155
H14···H492	3.332	H382···C50^xiv	3.227
H14···H511^x	2.546	H382···C51^xiv	3.573
H15···O31	2.737	H382···H20^xiii	2.980
H15···O32	3.431	H382···H35^xiv	2.499
H15···O33	3.573	H382···H50^xiv	3.042
H15···C31	3.540	H382···H212^xiii	2.908
H15···C42^x	3.016	H391···C3^vi	3.114
H15···C43^x	3.295	H391···C5^vi	3.394
H15···C48	3.453	H391···H5^vi	2.972
H15···H42^x	2.528	H391···H31^vi	2.856
H15···H43^x	3.061	H391···H32^vi	2.641
H15···H47^x	3.371	H392···H31^vi	3.342
H15···H381^x	3.168	H392···H32^vi	3.584
H15···H492	3.005	H392···H35^xiv	3.234
H17···C37^x	3.530	H392···H36^xiv	3.253
H17···H371^x	3.132	H491···O12^vi	2.598
H17···H372^x	3.039	H491···C18^vi	3.480
H20···C37^x	3.234	H491···H32^vi	3.502
H20···C38^x	3.369	H491···H36^xiv	3.386
H20···H50^iv	2.970	H491···H45^vi	3.584
H20···H371^x	2.715	H491···H81ⁱⁱⁱ	3.498
H20···H372^x	3.002	H492···C14	3.162
H20···H381^x	3.100	H492···C15	2.960
H20···H382^x	2.980	H492···C16	3.498
H31···C36ⁱⁱ	3.462	H492···H14	3.332
H31···C39ⁱ	3.502	H492···H15	3.005
H31···H35ⁱⁱ	3.113	H492···H44^vi	3.340
H31···H36ⁱⁱ	2.739	H492···H45^vi	3.357
H31···H391ⁱ	2.856	H492···H81ⁱⁱⁱ	3.017
H31···H392ⁱ	3.342	H493···O11^vi	3.148
H32···C39ⁱ	3.507	H493···O12^vi	3.280
H32···H391ⁱ	2.641	H493···O13	3.529
H32···H392ⁱ	3.584	H493···C19	3.398
H32···H491ⁱ	3.502	H493···C45^vi	3.321
H32···H493ⁱ	3.393	H493···H32^vi	3.393
H35···C38^xii	3.348	H493···H44^vi	3.519
H35···H31^viii	3.113	H493···H45^vi	2.455
H35···H71^viii	3.290	H493···H191	2.587
H35···H212^vii	3.081	H511···C9ⁱ	3.482
H35···H382^xii	2.499	H511···C14^xiii	3.225
H35···H392^xii	3.234	H511···H13^xiii	3.533
H36···O12^viii	2.683	H511···H14^xiii	2.546
H36···C18^viii	3.599	H511···H82ⁱ	3.135
H36···H31^viii	2.739	H511···H91ⁱ	3.214
H36···H92^viii	3.345	H511···H92ⁱ	3.145
H36···H392^xii	3.253	H512···C9ⁱ	3.520
H36···H491^xii	3.386	H512···C37^xii	3.308
H42···O31^xiii	3.350	H512···H91ⁱ	3.488
H42···C15^xiii	3.180	H512···H92ⁱ	2.798
H42···H5^vi	2.922	H512···H192ⁱ	3.141
H42···H15^xiii	2.528	H512···H371^xii	2.454

C18—O13—C19	117.5 (2)	C34—C50—C51	130.1 (2)
C48—O33—C49	117.1 (2)	C1—N12—H121	116.9
C7—N11—C8	120.9 (3)	C16—N12—H121	116.9
C7—N11—C17	111.5 (2)	C31—N32—H321	117.4
C8—N11—C17	106.4 (2)	C46—N32—H321	117.4
C1—N12—C16	126.1 (2)	C2—C3—H31	110.7
C37—N31—C38	121.6 (2)	C2—C3—H32	110.7
C37—N31—C47	112.6 (2)	C4—C3—H31	110.7
C38—N31—C47	105.8 (2)	C4—C3—H32	110.7
C31—N32—C46	125.1 (2)	H31—C3—H32	109.5
O11—C1—N12	121.6 (2)	C4—C5—H5	117.9
O11—C1—C2	119.0 (2)	C6—C5—H5	117.9
N12—C1—C2	119.3 (2)	C5—C6—H6	118.8
C1—C2—C3	109.13 (19)	C7—C6—H6	118.8
C1—C2—C10	115.89 (18)	N11—C7—H71	109.5
C1—C2—C18	102.30 (19)	N11—C7—H72	109.5
C3—C2—C10	104.67 (18)	C6—C7—H71	109.5
C3—C2—C18	113.37 (19)	C6—C7—H72	109.5
C10—C2—C18	111.77 (19)	H71—C7—H72	109.5
C2—C3—C4	104.42 (19)	N11—C8—H81	111.5
C3—C4—C5	117.1 (2)	N11—C8—H82	111.5
C3—C4—C17	101.0 (2)	C9—C8—H81	111.5
C3—C4—C20	114.0 (2)	C9—C8—H82	111.5
C5—C4—C17	109.3 (2)	H81—C8—H82	109.5
C5—C4—C20	105.9 (2)	C8—C9—H91	110.3
C17—C4—C20	109.3 (2)	C8—C9—H92	110.3
C4—C5—C6	124.1 (3)	C10—C9—H91	110.3
C5—C6—C7	122.4 (3)	C10—C9—H92	110.3
N11—C7—C6	109.5 (3)	H91—C9—H92	109.5
N11—C8—C9	101.3 (2)	C11—C12—H12	119.4
C8—C9—C10	106.1 (2)	C13—C12—H12	119.4
C2—C10—C9	112.90 (19)	C12—C13—H13	119.8
C2—C10—C11	113.76 (19)	C14—C13—H13	119.8
C2—C10—C17	103.07 (18)	C13—C14—H14	120.1
C9—C10—C11	112.11 (19)	C15—C14—H14	120.1
C9—C10—C17	101.5 (2)	C14—C15—H15	120.2
C11—C10—C17	112.51 (18)	C16—C15—H15	120.2
C10—C11—C12	121.0 (2)	N11—C17—H17	112.6
C10—C11—C16	121.8 (2)	C4—C17—H17	112.6
C12—C11—C16	117.1 (2)	C10—C17—H17	112.6
C11—C12—C13	121.1 (2)	O13—C19—H191	109.5
C12—C13—C14	120.5 (2)	O13—C19—H192	109.5
C13—C14—C15	119.8 (2)	O13—C19—H193	109.5
C14—C15—C16	119.7 (2)	H191—C19—H192	109.5
N12—C16—C11	120.4 (2)	H191—C19—H193	109.5
N12—C16—C15	117.8 (2)	H192—C19—H193	109.5
C11—C16—C15	121.7 (2)	C4—C20—H20	115.8
N11—C17—C4	105.5 (2)	C21—C20—H20	115.8
N11—C17—C10	103.8 (2)	C20—C21—H211	120.0
C4—C17—C10	109.0 (2)	C20—C21—H212	120.0
O12—C18—O13	123.8 (2)	H211—C21—H212	120.0
O12—C18—C2	126.3 (2)	C32—C33—H331	110.6
O13—C18—C2	110.0 (2)	C32—C33—H332	110.6
C4—C20—C21	128.3 (3)	C34—C33—H331	110.6
O31—C31—N32	120.5 (2)	C34—C33—H332	110.6
O31—C31—C32	119.7 (2)	H331—C33—H332	109.5
N32—C31—C32	119.71 (18)	C34—C35—H35	117.9
C31—C32—C33	109.16 (18)	C36—C35—H35	117.9
C31—C32—C40	116.63 (18)	C35—C36—H36	118.9
C31—C32—C48	102.47 (19)	C37—C36—H36	118.9
C33—C32—C40	104.67 (18)	N31—C37—H371	109.7
C33—C32—C48	112.2 (2)	N31—C37—H372	109.7
C40—C32—C48	111.90 (18)	C36—C37—H371	109.7
C32—C33—C34	104.82 (19)	C36—C37—H372	109.7
C33—C34—C35	114.1 (2)	H371—C37—H372	109.5
C33—C34—C47	100.66 (19)	N31—C38—H381	111.7
C33—C34—C50	110.2 (2)	N31—C38—H382	111.7
C35—C34—C47	109.0 (2)	C39—C38—H381	111.7
C35—C34—C50	109.2 (2)	C39—C38—H382	111.7
C47—C34—C50	113.7 (2)	H381—C38—H382	109.5
C34—C35—C36	124.3 (2)	C38—C39—H391	110.6
C35—C36—C37	122.2 (2)	C38—C39—H392	110.6
N31—C37—C36	108.4 (2)	C40—C39—H391	110.6
N31—C38—C39	100.4 (2)	C40—C39—H392	110.6
C38—C39—C40	105.0 (2)	H391—C39—H392	109.5
C32—C40—C39	114.05 (18)	C41—C42—H42	119.0
C32—C40—C41	113.29 (18)	C43—C42—H42	119.0
C32—C40—C47	103.05 (17)	C42—C43—H43	119.9
C39—C40—C41	111.09 (19)	C44—C43—H43	119.9
C39—C40—C47	102.14 (19)	C43—C44—H44	120.0
C41—C40—C47	112.42 (18)	C45—C44—H44	120.0
C40—C41—C42	121.4 (2)	C44—C45—H45	120.3
C40—C41—C46	122.13 (18)	C46—C45—H45	120.3
C42—C41—C46	116.4 (2)	N31—C47—H47	111.7
C41—C42—C43	121.9 (2)	C34—C47—H47	111.7
C42—C43—C44	120.2 (2)	C40—C47—H47	111.7
C43—C44—C45	120.1 (3)	O33—C49—H491	109.5
C44—C45—C46	119.3 (2)	O33—C49—H492	109.5
N32—C46—C41	121.0 (2)	O33—C49—H493	109.5
N32—C46—C45	117.1 (2)	H491—C49—H492	109.5
C41—C46—C45	122.0 (2)	H491—C49—H493	109.5
N31—C47—C34	108.41 (19)	H492—C49—H493	109.5
N31—C47—C40	104.33 (18)	C34—C50—H50	114.9
C34—C47—C40	108.71 (18)	C51—C50—H50	114.9
O32—C48—O33	124.3 (2)	C50—C51—H511	120.0
O32—C48—C32	125.5 (2)	C50—C51—H512	120.0
O33—C48—C32	110.2 (2)	H511—C51—H512	120.0

C19—O13—C18—O12	0.1 (3)	C11—C10—C17—C4	−112.7 (2)
C19—O13—C18—C2	−179.91 (19)	C17—C10—C11—C12	−74.4 (2)
C49—O33—C48—O32	2.3 (4)	C17—C10—C11—C16	103.8 (2)
C49—O33—C48—C32	−179.4 (2)	C10—C11—C12—C13	179.3 (2)
C7—N11—C8—C9	175.3 (3)	C10—C11—C16—N12	−0.5 (3)
C8—N11—C7—C6	−179.2 (3)	C10—C11—C16—C15	179.7 (2)
C7—N11—C17—C4	71.7 (3)	C12—C11—C16—N12	177.7 (2)
C7—N11—C17—C10	−173.7 (2)	C12—C11—C16—C15	−2.1 (3)
C17—N11—C7—C6	−53.1 (4)	C16—C11—C12—C13	1.1 (3)
C8—N11—C17—C4	−154.6 (2)	C11—C12—C13—C14	0.4 (4)
C8—N11—C17—C10	−40.0 (3)	C12—C13—C14—C15	−0.9 (4)
C17—N11—C8—C9	46.9 (3)	C13—C14—C15—C16	−0.1 (3)
C1—N12—C16—C11	9.9 (3)	C14—C15—C16—N12	−178.1 (2)
C1—N12—C16—C15	−170.3 (2)	C14—C15—C16—C11	1.6 (3)
C16—N12—C1—O11	174.6 (2)	O31—C31—C32—C33	52.2 (2)
C16—N12—C1—C2	−3.4 (3)	O31—C31—C32—C40	170.5 (2)
C37—N31—C38—C39	178.4 (2)	O31—C31—C32—C48	−67.0 (2)
C38—N31—C37—C36	176.5 (2)	N32—C31—C32—C33	−132.2 (2)
C37—N31—C47—C34	69.8 (2)	N32—C31—C32—C40	−13.9 (3)
C37—N31—C47—C40	−174.5 (2)	N32—C31—C32—C48	108.7 (2)
C47—N31—C37—C36	−56.4 (3)	C31—C32—C33—C34	88.5 (2)
C38—N31—C47—C34	−155.2 (2)	C31—C32—C40—C39	145.2 (2)
C38—N31—C47—C40	−39.4 (2)	C31—C32—C40—C41	16.8 (2)
C47—N31—C38—C39	48.3 (2)	C31—C32—C40—C47	−104.9 (2)
C31—N32—C46—C41	4.4 (3)	C31—C32—C48—O32	115.3 (2)
C31—N32—C46—C45	−176.8 (2)	C31—C32—C48—O33	−63.0 (2)
C46—N32—C31—O31	178.7 (2)	C33—C32—C40—C39	−94.1 (2)
C46—N32—C31—C32	3.1 (3)	C33—C32—C40—C41	137.5 (2)
O11—C1—C2—C3	53.1 (2)	C33—C32—C40—C47	15.8 (2)
O11—C1—C2—C10	170.9 (2)	C40—C32—C33—C34	−37.1 (2)
O11—C1—C2—C18	−67.2 (2)	C33—C32—C48—O32	−1.7 (3)
N12—C1—C2—C3	−128.8 (2)	C33—C32—C48—O33	−180.0 (2)
N12—C1—C2—C10	−11.0 (2)	C48—C32—C33—C34	−158.6 (2)
N12—C1—C2—C18	110.8 (2)	C40—C32—C48—O32	−119.0 (2)
C1—C2—C3—C4	87.7 (2)	C40—C32—C48—O33	62.7 (2)
C1—C2—C10—C9	147.3 (2)	C48—C32—C40—C39	27.7 (2)
C1—C2—C10—C11	18.1 (2)	C48—C32—C40—C41	−100.7 (2)
C1—C2—C10—C17	−104.0 (2)	C48—C32—C40—C47	137.5 (2)
C1—C2—C18—O12	122.1 (3)	C32—C33—C34—C35	159.2 (2)
C1—C2—C18—O13	−57.9 (2)	C32—C33—C34—C47	42.7 (2)
C3—C2—C10—C9	−92.5 (2)	C32—C33—C34—C50	−77.6 (2)
C3—C2—C10—C11	138.31 (19)	C33—C34—C35—C36	−106.5 (3)
C3—C2—C10—C17	16.2 (2)	C33—C34—C47—N31	80.1 (2)
C10—C2—C3—C4	−37.0 (2)	C33—C34—C47—C40	−32.8 (2)
C3—C2—C18—O12	4.7 (4)	C33—C34—C50—C51	138.5 (4)
C3—C2—C18—O13	−175.3 (2)	C35—C34—C47—N31	−40.2 (2)
C18—C2—C3—C4	−159.0 (2)	C35—C34—C47—C40	−153.0 (2)
C10—C2—C18—O12	−113.3 (3)	C47—C34—C35—C36	5.1 (4)
C10—C2—C18—O13	66.7 (2)	C35—C34—C50—C51	−95.6 (4)
C18—C2—C10—C9	30.6 (2)	C50—C34—C35—C36	129.8 (3)
C18—C2—C10—C11	−98.6 (2)	C47—C34—C50—C51	26.4 (5)
C18—C2—C10—C17	139.3 (2)	C50—C34—C47—N31	−162.2 (2)
C2—C3—C4—C5	160.8 (2)	C50—C34—C47—C40	85.0 (2)
C2—C3—C4—C17	42.3 (2)	C34—C35—C36—C37	6.8 (5)
C2—C3—C4—C20	−74.8 (2)	C35—C36—C37—N31	17.5 (4)
C3—C4—C5—C6	−106.2 (3)	N31—C38—C39—C40	−37.7 (2)
C3—C4—C17—N11	78.6 (2)	C38—C39—C40—C32	125.0 (2)
C3—C4—C17—C10	−32.4 (2)	C38—C39—C40—C41	−105.5 (2)
C3—C4—C20—C21	−56.2 (4)	C38—C39—C40—C47	14.6 (2)
C5—C4—C17—N11	−45.5 (2)	C32—C40—C41—C42	171.5 (2)
C5—C4—C17—C10	−156.4 (2)	C32—C40—C41—C46	−10.6 (3)
C17—C4—C5—C6	7.7 (4)	C32—C40—C47—N31	−104.76 (19)
C5—C4—C20—C21	74.1 (4)	C32—C40—C47—C34	10.8 (2)
C20—C4—C5—C6	125.4 (3)	C39—C40—C41—C42	41.6 (3)
C17—C4—C20—C21	−168.3 (3)	C39—C40—C41—C46	−140.5 (2)
C20—C4—C17—N11	−161.0 (2)	C39—C40—C47—N31	13.8 (2)
C20—C4—C17—C10	88.1 (2)	C39—C40—C47—C34	129.30 (19)
C4—C5—C6—C7	11.5 (6)	C41—C40—C47—N31	132.92 (19)
C5—C6—C7—N11	10.7 (5)	C41—C40—C47—C34	−111.6 (2)
N11—C8—C9—C10	−35.6 (3)	C47—C40—C41—C42	−72.2 (2)
C8—C9—C10—C2	121.2 (2)	C47—C40—C41—C46	105.7 (2)
C8—C9—C10—C11	−108.7 (2)	C40—C41—C42—C43	177.7 (2)
C8—C9—C10—C17	11.6 (2)	C40—C41—C46—N32	0.2 (3)
C2—C10—C11—C12	168.9 (2)	C40—C41—C46—C45	−178.6 (2)
C2—C10—C11—C16	−12.9 (2)	C42—C41—C46—N32	178.2 (2)
C2—C10—C17—N11	−101.9 (2)	C42—C41—C46—C45	−0.6 (3)
C2—C10—C17—C4	10.2 (2)	C46—C41—C42—C43	−0.4 (4)
C9—C10—C11—C12	39.3 (2)	C41—C42—C43—C44	0.0 (4)
C9—C10—C11—C16	−142.6 (2)	C42—C43—C44—C45	1.2 (5)
C9—C10—C17—N11	15.2 (2)	C43—C44—C45—C46	−2.1 (5)
C9—C10—C17—C4	127.3 (2)	C44—C45—C46—N32	−177.0 (2)
C11—C10—C17—N11	135.2 (2)	C44—C45—C46—C41	1.8 (4)

Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) x, y−1, z; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+2, y−1/2, −z+3/2; (v) −x+1, y−1/2, −z+3/2; (vi) x−1/2, −y+1/2, −z+1; (vii) −x+2, y+1/2, −z+3/2; (viii) x, y+1, z; (ix) −x+3/2, −y, z−1/2; (x) −x+3/2, −y+1, z+1/2; (xi) −x+3/2, −y, z+1/2; (xii) x+1/2, −y+3/2, −z+1; (xiii) −x+3/2, −y+1, z−1/2; (xiv) x−1/2, −y+3/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N12—H121···O31	0.86	2.06	2.845 (2)	152
N32—H321···O11	0.86	2.08	2.882 (2)	156

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