(+)-cis-1-Acetyl-4-(4-{[(2R,4S)-2-(2,4-di­chloro­phenyl)-2-(1H-imidazol-1-ylmeth­yl)-1,3-dioxolan-4-yl]­methoxy}phenyl)­piperazine [(2R,4S)-(+)-ketoconazole]

The title compound, C₂₆H₂₈Cl₂N₄O₄, the (+)-enantiomer of the orally active broad-spectrum antifungal agent ketoconazole, crystallizes in space group P1 with two mol­ecules in the unit cell. Both mol­ecules have the 2R,4S configuration, but the achiral parts of the mol­ecules are packed in a pseudo-centrosymmetric fashion.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.108
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry .....         91 PerFit
PLAT113_ALERT_2_B ADDSYM Suggests Possible Pseudo/New Spacegroup .        P-1

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

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           69.21
           From the CIF: _reflns_number_total               8445
           Count of symmetry unique reflns         4686
           Completeness (_total/calc)            180.22%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3759
           Fraction of Friedel pairs measured     0.802
           Are heavy atom types Z>Si present          yes

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

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

---

Computing details

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff, 1996); software used to prepare material for publication: PARST (Nardelli, 1983).

(+)-cis-1-Acetyl-4-[4-[[(2R,4S)-2-(2,4-dichloro-phenyl) -2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine,

Crystal data

C26H28Cl2N4O4	Z = 2
Mr = 531.42	F(000) = 556
Triclinic, P1	Dx = 1.405 Mg m^−3
a = 10.3740 (5) Å	Cu Kα radiation, λ = 1.54178 Å
b = 10.8633 (7) Å	Cell parameters from 38 reflections
c = 13.2251 (4) Å	θ = 11.2–28.0°
α = 67.725 (3)°	µ = 2.66 mm^−1
β = 79.262 (4)°	T = 293 K
γ = 65.743 (4)°	Prism, colourless
V = 1256.60 (12) Å^3	0.60 × 0.36 × 0.22 mm

Data collection

Siemens P4 four-circle diffractometer	Rint = 0.000
ω/2θ scans	θmax = 69.2°
Absorption correction: ψ scan XEMP (Siemens, 1989)	h = −12→12
Tmin = 0.344, Tmax = 0.557	k = −12→12
8445 measured reflections	l = −16→16
8445 independent reflections	3 standard reflections every 100 reflections
8257 reflections with F^2 > 2σ(F^2)	intensity decay: none

Refinement

Refinement on F^2	w = 1/[σ^2(Fo^2) + (0.0737P)^2 + 0.1938P] where P = (Fo^2 + 2Fc^2)/3
Least-squares matrix: full	(Δ/σ)max < 0.001
R[F^2 > 2σ(F^2)] = 0.039	Δρmax = 0.23 e Å^−3
wR(F^2) = 0.108	Δρmin = −0.25 e Å^−3
S = 1.05	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin((2θ)]^-1/4
8445 reflections	Extinction coefficient: 0.0274 (9)
652 parameters	Absolute structure: Flack (1983); 3977 Friedel pairs
H-atom parameters constrained	Absolute structure parameter: 0.017 (8)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.7461 (2)	0.3560 (2)	0.8609 (2)	0.0404 (9)*
C2	0.6819 (3)	0.4981 (3)	0.8420 (2)	0.046 (1)*
N3	0.6844 (3)	0.5749 (3)	0.7383 (2)	0.053 (1)*
C4	0.7532 (4)	0.4757 (3)	0.6866 (2)	0.054 (1)*
C5	0.7912 (3)	0.3422 (3)	0.7608 (2)	0.052 (1)*
C6	0.7554 (3)	0.2447 (3)	0.9664 (2)	0.042 (1)*
C7	0.6351 (2)	0.1892 (3)	0.9922 (2)	0.035 (1)*
O8	0.5025 (2)	0.3063 (2)	0.9815 (1)	0.0406 (7)*
C9	0.4200 (3)	0.3050 (3)	0.9053 (2)	0.043 (1)*
C10	0.4965 (3)	0.1575 (3)	0.8979 (2)	0.049 (1)*
O11	0.6403 (2)	0.1275 (2)	0.9148 (1)	0.0416 (7)*
C12	0.6480 (2)	0.0850 (3)	1.1109 (2)	0.036 (1)*
C13	0.7477 (3)	−0.0546 (3)	1.1444 (2)	0.038 (1)*
C14	0.7613 (3)	−0.1410 (3)	1.2537 (2)	0.043 (1)*
C15	0.6750 (3)	−0.0859 (3)	1.3314 (2)	0.047 (1)*
C16	0.5762 (3)	0.0517 (4)	1.3022 (2)	0.054 (1)*
C17	0.5641 (3)	0.1353 (3)	1.1927 (2)	0.046 (1)*
Cl18	0.86163 (6)	−0.13223 (7)	1.05130 (5)	0.0523 (3)*
Cl19	0.6918 (1)	−0.19401 (9)	1.46813 (6)	0.0693 (4)*
C20	0.4174 (3)	0.4276 (3)	0.8007 (2)	0.046 (1)*
O21	0.3177 (2)	0.4395 (2)	0.7322 (2)	0.0518 (8)*
C22	0.2808 (3)	0.5619 (3)	0.6416 (2)	0.043 (1)*
C23	0.1690 (3)	0.5873 (3)	0.5839 (2)	0.047 (1)*
C24	0.1241 (3)	0.7078 (3)	0.4920 (2)	0.045 (1)*
C25	0.1889 (3)	0.8081 (3)	0.4534 (2)	0.039 (1)*
C26	0.3015 (3)	0.7798 (3)	0.5130 (2)	0.050 (1)*
C27	0.3482 (3)	0.6587 (3)	0.6048 (2)	0.054 (1)*
N28	0.1460 (2)	0.9265 (2)	0.3557 (2)	0.0415 (9)*
C29	−0.0058 (3)	0.9969 (3)	0.3385 (2)	0.044 (1)*
C30	−0.0357 (3)	1.0950 (3)	0.2225 (2)	0.049 (1)*
N31	0.0290 (2)	1.2011 (2)	0.1933 (2)	0.048 (1)*
C32	0.1797 (3)	1.1362 (3)	0.2131 (2)	0.051 (1)*
C33	0.2105 (3)	1.0330 (3)	0.3284 (2)	0.046 (1)*
C34	−0.0465 (3)	1.3407 (3)	0.1454 (2)	0.046 (1)*
O35	−0.1694 (2)	1.3836 (2)	0.1195 (2)	0.064 (1)*
C36	0.0226 (4)	1.4467 (3)	0.1253 (3)	0.063 (2)*
N51	0.2458 (2)	0.6466 (2)	0.1298 (2)	0.0399 (9)*
C52	0.3126 (3)	0.5055 (3)	0.1480 (2)	0.050 (1)*
N53	0.3034 (3)	0.4272 (3)	0.2509 (2)	0.058 (1)*
C54	0.2239 (4)	0.5259 (3)	0.3007 (2)	0.055 (1)*
C55	0.1881 (3)	0.6612 (3)	0.2287 (2)	0.050 (1)*
C56	0.2369 (3)	0.7605 (3)	0.0240 (2)	0.040 (1)*
C57	0.3615 (2)	0.8088 (2)	−0.0013 (2)	0.034 (1)*
O58	0.3695 (2)	0.8649 (2)	0.0782 (1)	0.0379 (7)*
C59	0.5082 (3)	0.7873 (3)	0.1231 (2)	0.0406 (9)*
C60	0.5925 (3)	0.7166 (3)	0.0415 (2)	0.046 (1)*
O61	0.4881 (2)	0.6876 (2)	0.0058 (1)	0.0394 (7)*
C62	0.3467 (2)	0.9183 (2)	−0.1178 (2)	0.0338 (9)*
C63	0.2491 (2)	1.0589 (3)	−0.1474 (2)	0.036 (1)*
C64	0.2340 (3)	1.1499 (3)	−0.2554 (2)	0.044 (1)*
C65	0.3177 (3)	1.0984 (3)	−0.3358 (2)	0.046 (1)*
C66	0.4130 (3)	0.9609 (3)	−0.3110 (2)	0.051 (1)*
C67	0.4266 (3)	0.8732 (3)	−0.2025 (2)	0.045 (1)*
Cl68	0.13845 (6)	1.13227 (6)	−0.05140 (5)	0.0487 (3)*
Cl69	0.2979 (1)	1.21005 (9)	−0.47200 (5)	0.0714 (4)*
C70	0.5021 (3)	0.6797 (3)	0.2365 (2)	0.046 (1)*
O71	0.6391 (2)	0.6269 (2)	0.2785 (2)	0.0561 (9)*
C72	0.6795 (3)	0.4990 (3)	0.3645 (2)	0.046 (1)*
C73	0.8210 (3)	0.4356 (3)	0.3879 (2)	0.048 (1)*
C74	0.8732 (3)	0.3064 (3)	0.4714 (2)	0.044 (1)*
C75	0.7840 (3)	0.2371 (3)	0.5363 (2)	0.041 (1)*
C76	0.6409 (3)	0.3057 (3)	0.5139 (2)	0.057 (1)*
C77	0.5882 (3)	0.4341 (3)	0.4291 (2)	0.059 (1)*
N78	0.8330 (2)	0.1066 (2)	0.6251 (2)	0.043 (1)*
C79	0.9829 (3)	0.0436 (3)	0.6478 (2)	0.043 (1)*
C80	1.0095 (3)	−0.0687 (3)	0.7610 (2)	0.050 (1)*
N81	0.9557 (2)	−0.1773 (2)	0.7728 (2)	0.0473 (9)*
C82	0.8080 (3)	−0.1192 (3)	0.7441 (3)	0.058 (1)*
C83	0.7839 (3)	−0.0052 (3)	0.6327 (2)	0.053 (1)*
C84	1.0283 (3)	−0.3165 (3)	0.8303 (2)	0.045 (1)*
O85	1.1407 (2)	−0.3528 (2)	0.8724 (2)	0.056 (1)*
C86	0.9708 (4)	−0.4266 (3)	0.8400 (3)	0.061 (1)*
H2	0.6401	0.5376	0.8969	0.055*
H4	0.7710	0.4973	0.6116	0.065*
H5	0.8391	0.2567	0.7463	0.062*
H6A	0.7550	0.2818	1.0226	0.050*
H6B	0.8449	0.1651	0.9686	0.050*
H9	0.3235	0.3169	0.9353	0.052*
H10A	0.4618	0.0886	0.9540	0.059*
H10B	0.4867	0.1565	0.8267	0.059*
H14	0.8275	−0.2345	1.2741	0.052*
H16	0.5184	0.0881	1.3551	0.064*
H17	0.4973	0.2286	1.1731	0.056*
H20A	0.3888	0.5160	0.8159	0.056*
H20B	0.5106	0.4086	0.7649	0.056*
H23	0.1235	0.5226	0.6071	0.057*
H24	0.0485	0.7226	0.4548	0.055*
H26	0.3469	0.8445	0.4905	0.059*
H27	0.4248	0.6423	0.6417	0.064*
H29A	−0.0501	1.0518	0.3874	0.053*
H29B	−0.0463	0.9249	0.3558	0.053*
H30A	0.0016	1.0392	0.1738	0.059*
H30B	−0.1371	1.1434	0.2140	0.059*
H32A	0.2150	1.2111	0.2001	0.061*
H32B	0.2291	1.0856	0.1621	0.061*
H33A	0.3120	0.9845	0.3361	0.056*
H33B	0.1740	1.0860	0.3791	0.056*
H36A	0.0937	1.4380	0.0677	0.075*
H36B	0.0655	1.4270	0.1909	0.075*
H36C	−0.0476	1.5423	0.1045	0.075*
H52	0.3605	0.4670	0.0935	0.060*
H54	0.1978	0.5029	0.3747	0.066*
H55	0.1356	0.7460	0.2431	0.060*
H56A	0.1499	0.8422	0.0234	0.048*
H56B	0.2329	0.7266	−0.0330	0.048*
H59	0.5468	0.8542	0.1266	0.049*
H60A	0.6290	0.7803	−0.0187	0.056*
H60B	0.6705	0.6288	0.0752	0.056*
H64	0.1686	1.2438	−0.2733	0.052*
H66	0.4679	0.9266	−0.3658	0.062*
H67	0.4924	0.7796	−0.1857	0.054*
H70A	0.4296	0.7257	0.2827	0.055*
H70B	0.4820	0.6022	0.2321	0.055*
H73	0.8824	0.4806	0.3467	0.057*
H74	0.9694	0.2650	0.4846	0.053*
H76	0.5783	0.2638	0.5574	0.069*
H77	0.4921	0.4765	0.4156	0.071*
H79A	1.0147	0.1182	0.6428	0.051*
H79B	1.0366	−0.0001	0.5936	0.051*
H80A	1.1102	−0.1133	0.7731	0.059*
H80B	0.9635	−0.0232	0.8155	0.059*
H82A	0.7478	−0.0786	0.7981	0.070*
H82B	0.7825	−0.1960	0.7446	0.070*
H83A	0.8340	−0.0486	0.5776	0.063*
H83B	0.6838	0.0376	0.6183	0.063*
H86A	1.0451	−0.5199	0.8597	0.073*
H86B	0.9344	−0.4055	0.7713	0.073*
H86C	0.8963	−0.4250	0.8954	0.073*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.041 (1)	0.036 (1)	0.039 (1)	−0.0135 (9)	−0.0042 (8)	−0.0076 (8)
C2	0.050 (2)	0.036 (1)	0.050 (1)	−0.013 (1)	−0.003 (1)	−0.015 (1)
N3	0.062 (1)	0.038 (1)	0.052 (1)	−0.019 (1)	−0.007 (1)	−0.006 (1)
C4	0.066 (2)	0.050 (2)	0.038 (1)	−0.021 (2)	0.001 (1)	−0.009 (1)
C5	0.058 (2)	0.039 (1)	0.045 (1)	−0.009 (1)	0.005 (1)	−0.015 (1)
C6	0.041 (1)	0.040 (1)	0.038 (1)	−0.015 (1)	−0.0120 (9)	−0.003 (1)
C7	0.033 (1)	0.031 (1)	0.034 (1)	−0.007 (1)	−0.0078 (8)	−0.0067 (9)
O8	0.0355 (8)	0.0353 (9)	0.0395 (8)	−0.0017 (7)	−0.0111 (7)	−0.0087 (7)
C9	0.033 (1)	0.045 (1)	0.042 (1)	−0.011 (1)	−0.0153 (9)	−0.002 (1)
C10	0.053 (2)	0.043 (2)	0.050 (1)	−0.019 (1)	−0.025 (1)	−0.003 (1)
O11	0.0427 (9)	0.0389 (9)	0.0407 (9)	−0.0086 (8)	−0.0117 (7)	−0.0136 (7)
C12	0.034 (1)	0.034 (1)	0.034 (1)	−0.011 (1)	−0.0086 (9)	−0.0040 (9)
C13	0.034 (1)	0.038 (1)	0.040 (1)	−0.013 (1)	−0.0072 (9)	−0.009 (1)
C14	0.044 (1)	0.031 (1)	0.047 (1)	−0.012 (1)	−0.020 (1)	0.001 (1)
C15	0.052 (2)	0.049 (2)	0.037 (1)	−0.024 (1)	−0.008 (1)	−0.002 (1)
C16	0.056 (2)	0.055 (2)	0.039 (1)	−0.016 (1)	−0.002 (1)	−0.012 (1)
C17	0.048 (2)	0.038 (1)	0.040 (1)	−0.007 (1)	−0.003 (1)	−0.009 (1)
Cl18	0.0443 (3)	0.0429 (4)	0.0534 (3)	−0.0014 (3)	−0.0047 (3)	−0.0144 (3)
Cl19	0.0903 (6)	0.0657 (5)	0.0387 (3)	−0.0331 (4)	−0.0128 (3)	0.0055 (3)
C20	0.045 (1)	0.041 (1)	0.043 (1)	−0.011 (1)	−0.019 (1)	0.000 (1)
O21	0.057 (1)	0.043 (1)	0.0469 (9)	−0.0177 (9)	−0.0272 (8)	0.0039 (8)
C22	0.045 (1)	0.035 (1)	0.038 (1)	−0.007 (1)	−0.014 (1)	−0.0045 (9)
C23	0.052 (2)	0.040 (1)	0.046 (1)	−0.017 (1)	−0.017 (1)	−0.005 (1)
C24	0.051 (1)	0.040 (1)	0.043 (1)	−0.015 (1)	−0.021 (1)	−0.005 (1)
C25	0.039 (1)	0.037 (1)	0.035 (1)	−0.009 (1)	−0.0089 (9)	−0.010 (1)
C26	0.047 (1)	0.049 (2)	0.048 (1)	−0.020 (1)	−0.018 (1)	−0.002 (1)
C27	0.049 (1)	0.056 (2)	0.050 (1)	−0.021 (1)	−0.023 (1)	−0.002 (1)
N28	0.039 (1)	0.040 (1)	0.039 (1)	−0.0134 (9)	−0.0119 (8)	−0.0035 (9)
C29	0.039 (1)	0.042 (1)	0.047 (1)	−0.013 (1)	−0.014 (1)	−0.006 (1)
C30	0.051 (2)	0.042 (1)	0.049 (1)	−0.016 (1)	−0.020 (1)	−0.003 (1)
N31	0.048 (1)	0.038 (1)	0.049 (1)	−0.016 (1)	−0.015 (1)	0.0006 (9)
C32	0.043 (1)	0.045 (1)	0.050 (1)	−0.014 (1)	−0.008 (1)	−0.001 (1)
C33	0.042 (1)	0.045 (1)	0.047 (1)	−0.017 (1)	−0.013 (1)	−0.004 (1)
C34	0.054 (2)	0.040 (1)	0.038 (1)	−0.012 (1)	−0.013 (1)	−0.007 (1)
O35	0.061 (1)	0.044 (1)	0.077 (1)	−0.007 (1)	−0.032 (1)	−0.010 (1)
C36	0.075 (2)	0.046 (2)	0.063 (2)	−0.026 (2)	−0.017 (2)	−0.005 (1)
N51	0.041 (1)	0.035 (1)	0.038 (1)	−0.0133 (9)	−0.0044 (8)	−0.0055 (8)
C52	0.061 (2)	0.039 (1)	0.051 (2)	−0.020 (1)	−0.001 (1)	−0.013 (1)
N53	0.073 (2)	0.040 (1)	0.052 (1)	−0.022 (1)	−0.004 (1)	−0.005 (1)
C54	0.068 (2)	0.047 (2)	0.041 (1)	−0.022 (2)	−0.002 (1)	−0.006 (1)
C55	0.056 (2)	0.043 (2)	0.043 (1)	−0.013 (1)	0.004 (1)	−0.013 (1)
C56	0.041 (1)	0.038 (1)	0.037 (1)	−0.017 (1)	−0.0085 (9)	−0.004 (1)
C57	0.032 (1)	0.031 (1)	0.034 (1)	−0.007 (1)	−0.0072 (8)	−0.0092 (9)
O58	0.0394 (9)	0.0324 (8)	0.0356 (8)	−0.0058 (7)	−0.0126 (7)	−0.0083 (7)
C59	0.041 (1)	0.033 (1)	0.043 (1)	−0.012 (1)	−0.0167 (9)	−0.0027 (9)
C60	0.034 (1)	0.044 (1)	0.048 (1)	−0.008 (1)	−0.011 (1)	−0.005 (1)
O61	0.0370 (9)	0.0316 (9)	0.0408 (8)	−0.0039 (7)	−0.0085 (7)	−0.0095 (7)
C62	0.031 (1)	0.032 (1)	0.034 (1)	−0.010 (1)	−0.0061 (9)	−0.0073 (9)
C63	0.032 (1)	0.035 (1)	0.038 (1)	−0.011 (1)	−0.0077 (9)	−0.0071 (9)
C64	0.044 (1)	0.036 (1)	0.045 (1)	−0.014 (1)	−0.012 (1)	−0.004 (1)
C65	0.053 (2)	0.047 (2)	0.035 (1)	−0.024 (1)	−0.010 (1)	−0.001 (1)
C66	0.055 (2)	0.056 (2)	0.037 (1)	−0.019 (1)	0.001 (1)	−0.012 (1)
C67	0.044 (1)	0.039 (1)	0.040 (1)	−0.005 (1)	−0.006 (1)	−0.010 (1)
Cl68	0.0425 (3)	0.0416 (3)	0.0463 (3)	−0.0016 (3)	−0.0042 (2)	−0.0127 (3)
Cl69	0.0937 (6)	0.0666 (5)	0.0360 (3)	−0.0310 (5)	−0.0109 (3)	0.0063 (3)
C70	0.047 (1)	0.043 (1)	0.040 (1)	−0.013 (1)	−0.017 (1)	−0.003 (1)
O71	0.060 (1)	0.049 (1)	0.052 (1)	−0.0242 (9)	−0.0307 (9)	0.0078 (8)
C72	0.052 (1)	0.041 (1)	0.038 (1)	−0.013 (1)	−0.018 (1)	−0.003 (1)
C73	0.050 (1)	0.045 (2)	0.044 (1)	−0.019 (1)	−0.010 (1)	−0.006 (1)
C74	0.038 (1)	0.046 (1)	0.040 (1)	−0.011 (1)	−0.0086 (9)	−0.008 (1)
C75	0.043 (1)	0.039 (1)	0.032 (1)	−0.010 (1)	−0.0086 (9)	−0.0063 (9)
C76	0.042 (1)	0.059 (2)	0.055 (2)	−0.020 (1)	−0.013 (1)	0.004 (1)
C77	0.043 (1)	0.063 (2)	0.056 (2)	−0.019 (1)	−0.019 (1)	0.003 (1)
N78	0.041 (1)	0.043 (1)	0.038 (1)	−0.013 (1)	−0.0114 (8)	−0.0043 (9)
C79	0.042 (1)	0.041 (1)	0.040 (1)	−0.014 (1)	−0.011 (1)	−0.007 (1)
C80	0.053 (2)	0.044 (2)	0.049 (1)	−0.016 (1)	−0.018 (1)	−0.007 (1)
N81	0.044 (1)	0.040 (1)	0.049 (1)	−0.014 (1)	−0.0135 (9)	−0.0029 (9)
C82	0.043 (1)	0.055 (2)	0.061 (2)	−0.019 (1)	−0.013 (1)	0.002 (1)
C83	0.047 (1)	0.049 (2)	0.056 (2)	−0.019 (1)	−0.018 (1)	−0.002 (1)
C84	0.048 (1)	0.042 (1)	0.040 (1)	−0.014 (1)	−0.007 (1)	−0.010 (1)
O85	0.055 (1)	0.044 (1)	0.064 (1)	−0.0104 (9)	−0.0258 (9)	−0.0092 (9)
C86	0.065 (2)	0.043 (2)	0.069 (2)	−0.020 (1)	−0.019 (2)	−0.006 (1)

Geometric parameters (Å, º)

N1—C2	1.347 (3)	N51—C52	1.341 (4)
N1—C5	1.363 (4)	N51—C55	1.372 (4)
N1—C6	1.447 (3)	N51—C56	1.462 (3)
C2—H2	0.930	C52—H52	0.930
C2—N3	1.309 (3)	C52—N53	1.313 (3)
N3—C4	1.373 (4)	N53—C54	1.367 (4)
C4—H4	0.930	C54—H54	0.930
C4—C5	1.348 (4)	C54—C55	1.352 (4)
C5—H5	0.930	C55—H55	0.930
C6—H6A	0.970	C56—H56A	0.970
C6—H6B	0.970	C56—H56B	0.970
C6—C7	1.530 (4)	C56—C57	1.524 (4)
C7—O8	1.424 (3)	C57—O58	1.430 (4)
C7—O11	1.404 (4)	C57—O61	1.413 (3)
C7—C12	1.539 (3)	C57—C62	1.536 (3)
O8—C9	1.446 (4)	O58—C59	1.441 (3)
C9—H9	0.980	C59—H59	0.980
C9—C10	1.501 (4)	C59—C60	1.499 (4)
C9—C20	1.508 (3)	C59—C70	1.521 (3)
C10—H10A	0.970	C60—H60A	0.970
C10—H10B	0.970	C60—H60B	0.970
C10—O11	1.433 (4)	C60—O61	1.442 (4)
C12—C13	1.392 (3)	C62—C63	1.391 (3)
C12—C17	1.391 (4)	C62—C67	1.386 (4)
C13—C14	1.389 (3)	C63—C64	1.388 (3)
C13—Cl18	1.746 (3)	C63—Cl68	1.742 (3)
C14—H14	0.930	C64—H64	0.930
C14—C15	1.378 (4)	C64—C65	1.381 (4)
C15—C16	1.374 (4)	C65—C66	1.360 (4)
C15—Cl19	1.738 (2)	C65—Cl69	1.742 (2)
C16—H16	0.930	C66—H66	0.930
C16—C17	1.383 (4)	C66—C67	1.384 (3)
C17—H17	0.930	C67—H67	0.930
C20—H20A	0.970	C70—H70A	0.970
C20—H20B	0.970	C70—H70B	0.970
C20—O21	1.434 (4)	C70—O71	1.429 (4)
O21—C22	1.377 (3)	O71—C72	1.378 (3)
C22—C23	1.383 (5)	C72—C73	1.379 (4)
C22—C27	1.385 (5)	C72—C77	1.383 (5)
C23—H23	0.930	C73—H73	0.930
C23—C24	1.382 (3)	C73—C74	1.380 (3)
C24—H24	0.930	C74—H74	0.930
C24—C25	1.397 (5)	C74—C75	1.395 (4)
C25—C26	1.396 (4)	C75—C76	1.391 (4)
C25—N28	1.416 (3)	C75—N78	1.420 (3)
C26—H26	0.930	C76—H76	0.930
C26—C27	1.387 (3)	C76—C77	1.385 (4)
C27—H27	0.930	C77—H77	0.930
N28—C29	1.459 (3)	N78—C79	1.456 (3)
N28—C33	1.465 (5)	N78—C83	1.463 (5)
C29—H29A	0.970	C79—H79A	0.970
C29—H29B	0.970	C79—H79B	0.970
C29—C30	1.501 (3)	C79—C80	1.516 (3)
C30—H30A	0.970	C80—H80A	0.970
C30—H30B	0.970	C80—H80B	0.970
C30—N31	1.460 (5)	C80—N81	1.447 (5)
N31—C32	1.454 (4)	N81—C82	1.461 (4)
N31—C34	1.340 (3)	N81—C84	1.356 (3)
C32—H32A	0.970	C82—H82A	0.970
C32—H32B	0.970	C82—H82B	0.970
C32—C33	1.508 (3)	C82—C83	1.505 (4)
C33—H33A	0.970	C83—H83A	0.970
C33—H33B	0.970	C83—H83B	0.970
C34—O35	1.230 (4)	C84—O85	1.235 (4)
C34—C36	1.511 (6)	C84—C86	1.497 (6)
C36—H36A	0.960	C86—H86A	0.960
C36—H36B	0.960	C86—H86B	0.960
C36—H36C	0.960	C86—H86C	0.960
C2—N1—C5	105.6 (2)	C52—N51—C55	106.5 (2)
C2—N1—C6	125.6 (2)	C52—N51—C56	125.8 (2)
C5—N1—C6	128.7 (2)	C55—N51—C56	127.7 (2)
N1—C2—H2	123.5	N51—C52—H52	123.5
N1—C2—N3	113.0 (3)	N51—C52—N53	113.0 (3)
H2—C2—N3	123.5	H52—C52—N53	123.5
C2—N3—C4	104.5 (2)	C52—N53—C54	103.8 (3)
N3—C4—H4	125.1	N53—C54—H54	124.3
N3—C4—C5	109.9 (3)	N53—C54—C55	111.4 (3)
H4—C4—C5	125.1	H54—C54—C55	124.3
N1—C5—C4	107.1 (2)	N51—C55—C54	105.3 (2)
N1—C5—H5	126.5	N51—C55—H55	127.3
C4—C5—H5	126.5	C54—C55—H55	127.3
N1—C6—H6A	108.8	N51—C56—H56A	109.0
N1—C6—H6B	108.8	N51—C56—H56B	109.0
N1—C6—C7	113.7 (2)	N51—C56—C57	113.0 (2)
H6A—C6—H6B	107.7	H56A—C56—H56B	107.8
H6A—C6—C7	108.8	H56A—C56—C57	109.0
H6B—C6—C7	108.8	H56B—C56—C57	109.0
C6—C7—O8	109.6 (2)	C56—C57—O58	111.4 (2)
C6—C7—O11	109.2 (2)	C56—C57—O61	108.5 (2)
C6—C7—C12	108.3 (2)	C56—C57—C62	107.9 (2)
O8—C7—O11	106.6 (2)	O58—C57—O61	106.0 (2)
O8—C7—C12	109.3 (2)	O58—C57—C62	112.5 (2)
O11—C7—C12	113.8 (2)	O61—C57—C62	110.4 (2)
C7—O8—C9	108.7 (2)	C57—O58—C59	108.5 (2)
O8—C9—H9	110.2	O58—C59—H59	110.2
O8—C9—C10	102.8 (2)	O58—C59—C60	103.0 (2)
O8—C9—C20	107.4 (2)	O58—C59—C70	110.5 (2)
H9—C9—C10	110.2	H59—C59—C60	110.2
H9—C9—C20	110.2	H59—C59—C70	110.2
C10—C9—C20	115.7 (2)	C60—C59—C70	112.6 (2)
C9—C10—H10A	111.2	C59—C60—H60A	111.4
C9—C10—H10B	111.2	C59—C60—H60B	111.4
C9—C10—O11	102.9 (2)	C59—C60—O61	101.8 (2)
H10A—C10—H10B	109.1	H60A—C60—H60B	109.3
H10A—C10—O11	111.2	H60A—C60—O61	111.4
H10B—C10—O11	111.2	H60B—C60—O61	111.4
C7—O11—C10	106.2 (2)	C57—O61—C60	105.5 (2)
C7—C12—C13	124.3 (2)	C57—C62—C63	124.8 (2)
C7—C12—C17	118.8 (2)	C57—C62—C67	118.8 (2)
C13—C12—C17	116.7 (3)	C63—C62—C67	116.2 (2)
C12—C13—C14	122.0 (2)	C62—C63—C64	122.1 (2)
C12—C13—Cl18	122.0 (2)	C62—C63—Cl68	122.2 (2)
C14—C13—Cl18	116.0 (2)	C64—C63—Cl68	115.8 (2)
C13—C14—H14	120.5	C63—C64—H64	120.6
C13—C14—C15	118.9 (2)	C63—C64—C65	118.8 (2)
H14—C14—C15	120.5	H64—C64—C65	120.6
C14—C15—C16	121.1 (3)	C64—C65—C66	121.2 (3)
C14—C15—Cl19	119.0 (2)	C64—C65—Cl69	119.4 (2)
C16—C15—Cl19	120.0 (2)	C66—C65—Cl69	119.4 (2)
C15—C16—H16	120.6	C65—C66—H66	120.7
C15—C16—C17	118.9 (3)	C65—C66—C67	118.7 (3)
H16—C16—C17	120.6	H66—C66—C67	120.7
C12—C17—C16	122.4 (2)	C62—C67—C66	123.0 (2)
C12—C17—H17	118.8	C62—C67—H67	118.5
C16—C17—H17	118.8	C66—C67—H67	118.5
C9—C20—H20A	110.3	C59—C70—H70A	110.7
C9—C20—H20B	110.3	C59—C70—H70B	110.7
C9—C20—O21	106.9 (2)	C59—C70—O71	105.1 (2)
H20A—C20—H20B	108.6	H70A—C70—H70B	108.8
H20A—C20—O21	110.3	H70A—C70—O71	110.7
H20B—C20—O21	110.3	H70B—C70—O71	110.7
C20—O21—C22	115.4 (2)	C70—O71—C72	117.8 (2)
O21—C22—C23	116.6 (2)	O71—C72—C73	116.3 (3)
O21—C22—C27	124.7 (3)	O71—C72—C77	124.7 (3)
C23—C22—C27	118.7 (3)	C73—C72—C77	119.0 (3)
C22—C23—H23	119.7	C72—C73—H73	119.4
C22—C23—C24	120.6 (3)	C72—C73—C74	121.1 (3)
H23—C23—C24	119.7	H73—C73—C74	119.4
C23—C24—H24	118.9	C73—C74—H74	119.5
C23—C24—C25	122.1 (3)	C73—C74—C75	121.1 (3)
H24—C24—C25	119.0	H74—C74—C75	119.5
C24—C25—C26	116.1 (3)	C74—C75—C76	116.8 (3)
C24—C25—N28	121.0 (2)	C74—C75—N78	122.7 (2)
C26—C25—N28	122.8 (2)	C76—C75—N78	120.4 (3)
C25—C26—H26	118.8	C75—C76—H76	118.8
C25—C26—C27	122.3 (3)	C75—C76—C77	122.4 (3)
H26—C26—C27	118.8	H76—C76—C77	118.8
C22—C27—C26	120.1 (3)	C72—C77—C76	119.6 (3)
C22—C27—H27	119.9	C72—C77—H77	120.2
C26—C27—H27	119.9	C76—C77—H77	120.2
C25—N28—C29	116.4 (2)	C75—N78—C79	117.9 (2)
C25—N28—C33	116.5 (2)	C75—N78—C83	116.5 (2)
C29—N28—C33	110.6 (2)	C79—N78—C83	109.9 (3)
N28—C29—H29A	109.4	N78—C79—H79A	109.5
N28—C29—H29B	109.4	N78—C79—H79B	109.5
N28—C29—C30	111.2 (2)	N78—C79—C80	110.6 (2)
H29A—C29—H29B	108.0	H79A—C79—H79B	108.1
H29A—C29—C30	109.4	H79A—C79—C80	109.5
H29B—C29—C30	109.4	H79B—C79—C80	109.5
C29—C30—H30A	109.6	C79—C80—H80A	109.5
C29—C30—H30B	109.6	C79—C80—H80B	109.5
C29—C30—N31	110.3 (2)	C79—C80—N81	110.8 (2)
H30A—C30—H30B	108.1	H80A—C80—H80B	108.1
H30A—C30—N31	109.6	H80A—C80—N81	109.5
H30B—C30—N31	109.6	H80B—C80—N81	109.5
C30—N31—C32	112.7 (3)	C80—N81—C82	113.7 (3)
C30—N31—C34	120.5 (3)	C80—N81—C84	119.9 (3)
C32—N31—C34	126.6 (3)	C82—N81—C84	124.4 (3)
N31—C32—H32A	109.2	N81—C82—H82A	109.4
N31—C32—H32B	109.2	N81—C82—H82B	109.4
N31—C32—C33	111.9 (2)	N81—C82—C83	111.0 (3)
H32A—C32—H32B	107.9	H82A—C82—H82B	108.0
H32A—C32—C33	109.2	H82A—C82—C83	109.4
H32B—C32—C33	109.2	H82B—C82—C83	109.4
N28—C33—C32	111.2 (2)	N78—C83—C82	111.3 (3)
N28—C33—H33A	109.4	N78—C83—H83A	109.4
N28—C33—H33B	109.4	N78—C83—H83B	109.4
C32—C33—H33A	109.4	C82—C83—H83A	109.4
C32—C33—H33B	109.4	C82—C83—H83B	109.4
H33A—C33—H33B	108.0	H83A—C83—H83B	108.0
N31—C34—O35	121.9 (3)	N81—C84—O85	120.9 (3)
N31—C34—C36	118.1 (3)	N81—C84—C86	118.7 (3)
O35—C34—C36	120.1 (3)	O85—C84—C86	120.4 (3)
C34—C36—H36A	109.5	C84—C86—H86A	109.5
C34—C36—H36B	109.5	C84—C86—H86B	109.5
C34—C36—H36C	109.5	C84—C86—H86C	109.5
H36A—C36—H36B	109.5	H86A—C86—H86B	109.5
H36A—C36—H36C	109.5	H86A—C86—H86C	109.5
H36B—C36—H36C	109.5	H86B—C86—H86C	109.5
C5—N1—C2—H2	179.2	C55—N51—C52—H52	179.8
C5—N1—C2—N3	−0.8 (3)	C55—N51—C52—N53	−0.2 (4)
C6—N1—C2—H2	2.5	C56—N51—C52—H52	0.2
C6—N1—C2—N3	−177.6 (3)	C56—N51—C52—N53	−179.8 (3)
C2—N1—C5—C4	0.4 (3)	C52—N51—C55—C54	−0.4 (3)
C2—N1—C5—H5	−179.6	C52—N51—C55—H55	179.6
C6—N1—C5—C4	177.0 (3)	C56—N51—C55—C54	179.3 (3)
C6—N1—C5—H5	−3.0	C56—N51—C55—H55	−0.7
C2—N1—C6—H6A	−29.3	C52—N51—C56—H56A	151.4
C2—N1—C6—H6B	−146.4	C52—N51—C56—H56B	34.0
C2—N1—C6—C7	92.1 (3)	C52—N51—C56—C57	−87.3 (3)
C5—N1—C6—H6A	154.7	C55—N51—C56—H56A	−28.2
C5—N1—C6—H6B	37.6	C55—N51—C56—H56B	−145.6
C5—N1—C6—C7	−83.9 (3)	C55—N51—C56—C57	93.1 (3)
N1—C2—N3—C4	0.8 (3)	N51—C52—N53—C54	0.7 (4)
H2—C2—N3—C4	−179.2	H52—C52—N53—C54	−179.3
C2—N3—C4—H4	179.4	C52—N53—C54—H54	179.1
C2—N3—C4—C5	−0.6 (4)	C52—N53—C54—C55	−0.9 (4)
N3—C4—C5—N1	0.1 (4)	N53—C54—C55—N51	0.8 (4)
N3—C4—C5—H5	−179.9	N53—C54—C55—H55	−179.2
H4—C4—C5—N1	−179.9	H54—C54—C55—N51	−179.2
H4—C4—C5—H5	0.1	H54—C54—C55—H55	0.8
N1—C6—C7—O8	−54.4 (3)	N51—C56—C57—O58	−60.8 (3)
N1—C6—C7—O11	62.1 (3)	N51—C56—C57—O61	55.5 (3)
N1—C6—C7—C12	−173.6 (2)	N51—C56—C57—C62	175.2 (2)
H6A—C6—C7—O8	67.1	H56A—C56—C57—O58	60.5
H6A—C6—C7—O11	−176.5	H56A—C56—C57—O61	176.8
H6A—C6—C7—C12	−52.1	H56A—C56—C57—C62	−63.5
H6B—C6—C7—O8	−175.8	H56B—C56—C57—O58	177.8
H6B—C6—C7—O11	−59.4	H56B—C56—C57—O61	−65.8
H6B—C6—C7—C12	65.0	H56B—C56—C57—C62	53.8
C6—C7—O8—C9	124.7 (2)	C56—C57—O58—C59	124.8 (2)
O11—C7—O8—C9	6.6 (3)	O61—C57—O58—C59	6.9 (3)
C12—C7—O8—C9	−116.8 (2)	C62—C57—O58—C59	−113.8 (2)
C6—C7—O11—C10	−145.6 (2)	C56—C57—O61—C60	−149.1 (2)
O8—C7—O11—C10	−27.3 (3)	O58—C57—O61—C60	−29.2 (2)
C12—C7—O11—C10	93.3 (2)	C62—C57—O61—C60	92.8 (2)
C6—C7—C12—C13	−75.6 (3)	C56—C57—C62—C63	73.9 (3)
C6—C7—C12—C17	98.4 (3)	C56—C57—C62—C67	−100.2 (3)
O8—C7—C12—C13	165.0 (2)	O58—C57—C62—C63	−49.4 (3)
O8—C7—C12—C17	−21.0 (3)	O58—C57—C62—C67	136.4 (3)
O11—C7—C12—C13	45.9 (3)	O61—C57—C62—C63	−167.6 (2)
O11—C7—C12—C17	−140.1 (3)	O61—C57—C62—C67	18.3 (3)
C7—O8—C9—H9	132.8	C57—O58—C59—H59	134.5
C7—O8—C9—C10	15.4 (3)	C57—O58—C59—C60	17.0 (3)
C7—O8—C9—C20	−107.1 (2)	C57—O58—C59—C70	−103.5 (2)
O8—C9—C10—H10A	88.0	O58—C59—C60—H60A	85.1
O8—C9—C10—H10B	−150.2	O58—C59—C60—H60B	−152.6
O8—C9—C10—O11	−31.1 (3)	O58—C59—C60—O61	−33.8 (3)
H9—C9—C10—H10A	−29.4	H59—C59—C60—H60A	−32.5
H9—C9—C10—H10B	92.4	H59—C59—C60—H60B	89.8
H9—C9—C10—O11	−148.5	H59—C59—C60—O61	−151.3
C20—C9—C10—H10A	−155.2	C70—C59—C60—H60A	−155.9
C20—C9—C10—H10B	−33.4	C70—C59—C60—H60B	−33.6
C20—C9—C10—O11	85.7 (3)	C70—C59—C60—O61	85.3 (3)
O8—C9—C20—H20A	−51.1	O58—C59—C70—H70A	−51.6
O8—C9—C20—H20B	68.9	O58—C59—C70—H70B	69.2
O8—C9—C20—O21	−171.1 (2)	O58—C59—C70—O71	−171.2 (2)
H9—C9—C20—H20A	69.0	H59—C59—C70—H70A	70.4
H9—C9—C20—H20B	−171.0	H59—C59—C70—H70B	−168.8
H9—C9—C20—O21	−51.0	H59—C59—C70—O71	−49.2
C10—C9—C20—H20A	−165.1	C60—C59—C70—H70A	−166.1
C10—C9—C20—H20B	−45.2	C60—C59—C70—H70B	−45.3
C10—C9—C20—O21	74.8 (3)	C60—C59—C70—O71	74.3 (3)
C9—C10—O11—C7	36.4 (3)	C59—C60—O61—C57	39.2 (3)
H10A—C10—O11—C7	−82.7	H60A—C60—O61—C57	−79.7
H10B—C10—O11—C7	155.5	H60B—C60—O61—C57	158.0
C7—C12—C13—C14	175.5 (3)	C57—C62—C63—C64	−175.3 (3)
C7—C12—C13—Cl18	−5.4 (4)	C57—C62—C63—Cl68	4.8 (4)
C17—C12—C13—C14	1.4 (4)	C67—C62—C63—C64	−1.0 (4)
C17—C12—C13—Cl18	−179.5 (2)	C67—C62—C63—Cl68	179.1 (2)
C7—C12—C17—C16	−175.3 (3)	C57—C62—C67—C66	175.1 (3)
C7—C12—C17—H17	4.7	C57—C62—C67—H67	−4.9
C13—C12—C17—C16	−0.9 (4)	C63—C62—C67—C66	0.4 (4)
C13—C12—C17—H17	179.1	C63—C62—C67—H67	−179.6
C12—C13—C14—H14	178.9	C62—C63—C64—H64	−179.4
C12—C13—C14—C15	−1.1 (4)	C62—C63—C64—C65	0.6 (4)
Cl18—C13—C14—H14	−0.3	Cl68—C63—C64—H64	0.4
Cl18—C13—C14—C15	179.7 (2)	Cl68—C63—C64—C65	−179.6 (2)
C13—C14—C15—C16	0.4 (5)	C63—C64—C65—C66	0.5 (5)
C13—C14—C15—Cl19	180.0 (2)	C63—C64—C65—Cl69	178.8 (2)
H14—C14—C15—C16	−179.6	H64—C64—C65—C66	−179.5
H14—C14—C15—Cl19	0.0	H64—C64—C65—Cl69	−1.2
C14—C15—C16—H16	−180.0	C64—C65—C66—H66	178.9
C14—C15—C16—C17	0.0 (5)	C64—C65—C66—C67	−1.1 (5)
Cl19—C15—C16—H16	0.5	Cl69—C65—C66—H66	0.6
Cl19—C15—C16—C17	−179.5 (3)	Cl69—C65—C66—C67	−179.4 (2)
C15—C16—C17—C12	0.2 (5)	C65—C66—C67—C62	0.6 (5)
C15—C16—C17—H17	−179.8	C65—C66—C67—H67	−179.4
H16—C16—C17—C12	−179.8	H66—C66—C67—C62	−179.4
H16—C16—C17—H17	0.2	H66—C66—C67—H67	0.6
C9—C20—O21—C22	168.4 (2)	C59—C70—O71—C72	−161.0 (2)
H20A—C20—O21—C22	48.3	H70A—C70—O71—C72	79.4
H20B—C20—O21—C22	−71.6	H70B—C70—O71—C72	−41.4
C20—O21—C22—C23	−170.1 (3)	C70—O71—C72—C73	166.5 (3)
C20—O21—C22—C27	10.5 (4)	C70—O71—C72—C77	−15.3 (4)
O21—C22—C23—H23	−0.3	O71—C72—C73—H73	0.8
O21—C22—C23—C24	179.7 (3)	O71—C72—C73—C74	−179.2 (3)
C27—C22—C23—H23	179.2	C77—C72—C73—H73	−177.4
C27—C22—C23—C24	−0.8 (4)	C77—C72—C73—C74	2.6 (5)
O21—C22—C27—C26	−179.2 (3)	O71—C72—C77—C76	−179.6 (3)
O21—C22—C27—H27	0.8	O71—C72—C77—H77	0.4
C23—C22—C27—C26	1.3 (4)	C73—C72—C77—C76	−1.5 (5)
C23—C22—C27—H27	−178.7	C73—C72—C77—H77	178.5
C22—C23—C24—H24	−179.8	C72—C73—C74—H74	178.8
C22—C23—C24—C25	0.2 (5)	C72—C73—C74—C75	−1.2 (5)
H23—C23—C24—H24	0.2	H73—C73—C74—H74	−1.2
H23—C23—C24—C25	−179.8	H73—C73—C74—C75	178.8
C23—C24—C25—C26	−0.1 (4)	C73—C74—C75—C76	−1.2 (4)
C23—C24—C25—N28	176.5 (3)	C73—C74—C75—N78	−177.9 (3)
H24—C24—C25—C26	179.9	H74—C74—C75—C76	178.8
H24—C24—C25—N28	−3.5	H74—C74—C75—N78	2.1
C24—C25—C26—H26	−179.4	C74—C75—C76—H76	−177.7
C24—C25—C26—C27	0.6 (4)	C74—C75—C76—C77	2.3 (5)
N28—C25—C26—H26	4.1	N78—C75—C76—H76	−1.0
N28—C25—C26—C27	−175.9 (3)	N78—C75—C76—C77	179.0 (3)
C24—C25—N28—C29	40.6 (4)	C74—C75—N78—C79	−0.5 (4)
C24—C25—N28—C33	174.0 (3)	C74—C75—N78—C83	−134.5 (3)
C26—C25—N28—C29	−143.0 (3)	C76—C75—N78—C79	−177.0 (3)
C26—C25—N28—C33	−9.7 (4)	C76—C75—N78—C83	49.0 (4)
C25—C26—C27—C22	−1.3 (5)	C75—C76—C77—C72	−1.0 (5)
C25—C26—C27—H27	178.7	C75—C76—C77—H77	179.0
H26—C26—C27—C22	178.7	H76—C76—C77—C72	179.0
H26—C26—C27—H27	−1.3	H76—C76—C77—H77	−1.0
C25—N28—C29—H29A	73.1	C75—N78—C79—H79A	43.4
C25—N28—C29—H29B	−45.0	C75—N78—C79—H79B	−75.0
C25—N28—C29—C30	−166.0 (2)	C75—N78—C79—C80	164.2 (2)
C33—N28—C29—H29A	−62.9	C83—N78—C79—H79A	−179.9
C33—N28—C29—H29B	179.0	C83—N78—C79—H79B	61.8
C33—N28—C29—C30	58.1 (3)	C83—N78—C79—C80	−59.0 (3)
C25—N28—C33—C32	168.5 (2)	C75—N78—C83—C82	−164.1 (3)
C25—N28—C33—H33A	47.5	C75—N78—C83—H83A	74.9
C25—N28—C33—H33B	−70.6	C75—N78—C83—H83B	−43.1
C29—N28—C33—C32	−55.6 (3)	C79—N78—C83—C82	58.4 (3)
C29—N28—C33—H33A	−176.6	C79—N78—C83—H83A	−62.5
C29—N28—C33—H33B	65.3	C79—N78—C83—H83B	179.4
N28—C29—C30—H30A	63.9	N78—C79—C80—H80A	176.8
N28—C29—C30—H30B	−177.6	N78—C79—C80—H80B	−64.9
N28—C29—C30—N31	−56.9 (3)	N78—C79—C80—N81	55.9 (3)
H29A—C29—C30—H30A	−175.2	H79A—C79—C80—H80A	−62.4
H29A—C29—C30—H30B	−56.7	H79A—C79—C80—H80B	55.9
H29A—C29—C30—N31	64.0	H79A—C79—C80—N81	176.8
H29B—C29—C30—H30A	−57.1	H79B—C79—C80—H80A	56.0
H29B—C29—C30—H30B	61.4	H79B—C79—C80—H80B	174.3
H29B—C29—C30—N31	−177.9	H79B—C79—C80—N81	−64.9
C29—C30—N31—C32	54.3 (3)	C79—C80—N81—C82	−52.6 (3)
C29—C30—N31—C34	−130.9 (3)	C79—C80—N81—C84	142.3 (3)
H30A—C30—N31—C32	−66.5	H80A—C80—N81—C82	−173.5
H30A—C30—N31—C34	108.4	H80A—C80—N81—C84	21.5
H30B—C30—N31—C32	175.0	H80B—C80—N81—C82	68.2
H30B—C30—N31—C34	−10.1	H80B—C80—N81—C84	−96.9
C30—N31—C32—H32A	−173.8	C80—N81—C82—H82A	−69.1
C30—N31—C32—H32B	68.4	C80—N81—C82—H82B	172.6
C30—N31—C32—C33	−52.7 (3)	C80—N81—C82—C83	51.8 (3)
C34—N31—C32—H32A	11.7	C84—N81—C82—H82A	95.2
C34—N31—C32—H32B	−106.1	C84—N81—C82—H82B	−23.0
C34—N31—C32—C33	132.8 (3)	C84—N81—C82—C83	−143.9 (3)
C30—N31—C34—O35	−3.6 (4)	C80—N81—C84—O85	−0.5 (4)
C30—N31—C34—C36	175.3 (3)	C80—N81—C84—C86	−179.3 (3)
C32—N31—C34—O35	170.5 (3)	C82—N81—C84—O85	−163.9 (3)
C32—N31—C34—C36	−10.6 (4)	C82—N81—C84—C86	17.3 (4)
N31—C32—C33—N28	53.0 (3)	N81—C82—C83—N78	−54.0 (3)
N31—C32—C33—H33A	173.9	N81—C82—C83—H83A	67.0
N31—C32—C33—H33B	−68.0	N81—C82—C83—H83B	−174.9
H32A—C32—C33—N28	174.0	H82A—C82—C83—N78	66.9
H32A—C32—C33—H33A	−65.0	H82A—C82—C83—H83A	−172.1
H32A—C32—C33—H33B	53.1	H82A—C82—C83—H83B	−54.1
H32B—C32—C33—N28	−68.1	H82B—C82—C83—N78	−174.9
H32B—C32—C33—H33A	52.8	H82B—C82—C83—H83A	−53.9
H32B—C32—C33—H33B	170.9	H82B—C82—C83—H83B	64.2
N31—C34—C36—H36A	71.4	N81—C84—C86—H86A	160.5
N31—C34—C36—H36B	−48.6	N81—C84—C86—H86B	40.5
N31—C34—C36—H36C	−168.6	N81—C84—C86—H86C	−79.5
O35—C34—C36—H36A	−109.7	O85—C84—C86—H86A	−18.3
O35—C34—C36—H36B	130.3	O85—C84—C86—H86B	−138.3
O35—C34—C36—H36C	10.3	O85—C84—C86—H86C	101.7

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O61^i	0.93	2.46	3.365 (3)	166
C6—H6A···O35^ii	0.97	2.38	3.296 (5)	158
C20—H20A···O85^iii	0.97	2.51	3.147 (3)	123
C52—H52···O8^iv	0.93	2.54	3.451 (4)	166
C56—H56B···O85^v	0.97	2.27	3.186 (4)	157
C60—H60B···O35^vi	0.97	2.40	3.321 (3)	159

Symmetry codes: (i) x, y, z+1; (ii) x+1, y−1, z+1; (iii) x−1, y+1, z; (iv) x, y, z−1; (v) x−1, y+1, z−1; (vi) x+1, y−1, z.