15-(4-Chloro­benzyl­amino)-2-methoxy­podocarpa-8,11,13-trien-15-one

John, N.; Butcher, R.J.; Bakare, O.

doi:10.1107/S1600536806034283

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15-(4-Chlorobenzylamino)-2-methoxypodocarpa-8,11,13-trien-15-one

N. John, R. J. Butcher and O. Bakare

At 93 K, the benzylic C—N bond of the title compound [systematic name: N-(4-chlorobenzyl)-6-methoxy-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxamide], C₂₅H₃₀ClNO₂, adopts almost perfect coplanarity with the amide carbonyl linkage, the dihedral angle between the C—N—C=O planes being only 2.5 (3)°. There is weak intermolecular N—H

O hydrogen bonding between the two independent molecules comprising the asymmetric unit involving the carbonyl O atoms; this extends to link neighboring molecules into a chain.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806034283/tk2059sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806034283/tk2059Isup2.hkl Contains datablock I

CCDC reference: 624998

checkCIF report

Key indicators

Single-crystal X-ray study
T = 93 K
Mean (C-C) = 0.003 Å
R factor = 0.034
wR factor = 0.090
Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.38 Ratio
PLAT413_ALERT_2_B Short Inter XH3 .. XHn     H16A   ..  H18A    ..       2.06 Ang.

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.95
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.44 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1A    -   C15A    ..       5.01 su
PLAT318_ALERT_2_C Check Hybridisation of  N1B    in Main Residue .          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         24

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           28.20
           From the CIF: _reflns_number_total               6817
           Count of symmetry unique reflns         5229
           Completeness (_total/calc)            130.37%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1588
           Fraction of Friedel pairs measured     0.304
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4A    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4B    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5A    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5B    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10A   = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10B   = .          S

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

   6 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
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

N-(4-chlorobenzyl)-6-methoxy-1,4a-dimethyl-1,2,3,4,4a,9,10,10a- octahydrophenanthrene-1-carboxamide top

Crystal data top

C₂₅H₃₀ClNO₂	Z = 2
M_r = 411.95	F(000) = 440
Triclinic, P1	D_x = 1.286 Mg m⁻³
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8466 (11) Å	Cell parameters from 6096 reflections
b = 10.2147 (10) Å	θ = 2.6–28.2°
c = 10.8492 (12) Å	µ = 0.20 mm⁻¹
α = 84.224 (2)°	T = 93 K
β = 80.232 (2)°	Chunk, colorless
γ = 82.956 (2)°	0.44 × 0.33 × 0.23 mm
V = 1063.7 (2) Å³

Data collection top

Bruker SMART 1K CCD diffractometer	6817 independent reflections
Radiation source: fine-focus sealed tube	6495 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
φ and ω scans	θ_max = 28.2°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→13
T_min = 0.878, T_max = 1	k = −12→13
8349 measured reflections	l = −14→14

Refinement top

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)] = 0.034	H-atom parameters constrained
wR(F²) = 0.090	w = 1/[σ²(F_o²) + (0.0716P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.002
6817 reflections	Δρ_max = 0.37 e Å⁻³
529 parameters	Δρ_min = −0.37 e Å⁻³
3 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (4)

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Cl1A	−0.23450 (5)	0.44272 (6)	0.98628 (5)	0.03252 (13)
O2A	0.59953 (18)	0.50082 (16)	−0.32281 (15)	0.0355 (4)
O1A	0.13785 (14)	0.61643 (12)	0.42192 (12)	0.0174 (3)
N1A	0.18590 (18)	0.39622 (15)	0.43150 (15)	0.0184 (3)
H1AC	0.1882	0.3220	0.3961	0.022*
C1A	0.2410 (2)	0.64694 (16)	0.03584 (17)	0.0166 (4)
H1AA	0.3231	0.6938	0.0007	0.020*
H1AB	0.1843	0.6480	−0.0314	0.020*
C2A	0.1562 (2)	0.72097 (16)	0.14345 (18)	0.0168 (4)
H2AA	0.2151	0.7281	0.2073	0.020*
H2AB	0.1241	0.8117	0.1114	0.020*
C3A	0.03142 (19)	0.64958 (17)	0.20365 (18)	0.0171 (4)
H3AA	−0.0299	0.6476	0.1405	0.021*
H3AB	−0.0216	0.6999	0.2729	0.021*
C4A	0.07193 (19)	0.50712 (17)	0.25549 (17)	0.0152 (4)
C5A	0.16121 (18)	0.43438 (16)	0.14392 (17)	0.0135 (3)
H5AA	0.0989	0.4425	0.0791	0.016*
C6A	0.1986 (2)	0.28455 (17)	0.16715 (18)	0.0164 (4)
H6AA	0.2812	0.2667	0.2096	0.020*
H6AB	0.1207	0.2443	0.2215	0.020*
C7A	0.2286 (2)	0.22586 (17)	0.04077 (18)	0.0193 (4)
H7AA	0.2654	0.1316	0.0526	0.023*
H7AB	0.1410	0.2298	0.0066	0.023*
C8A	0.33171 (19)	0.29804 (17)	−0.05268 (18)	0.0171 (4)
C9A	0.35543 (19)	0.42874 (17)	−0.03969 (18)	0.0163 (4)
C10A	0.29007 (18)	0.50183 (16)	0.07655 (17)	0.0140 (3)
C11A	0.4469 (2)	0.49055 (19)	−0.13320 (19)	0.0210 (4)
H11A	0.4642	0.5786	−0.1254	0.025*
C12A	0.5134 (2)	0.4268 (2)	−0.2374 (2)	0.0234 (4)
C13A	0.4918 (2)	0.2970 (2)	−0.2503 (2)	0.0247 (4)
H13A	0.5379	0.2522	−0.3208	0.030*
C14A	0.4016 (2)	0.23537 (19)	−0.1575 (2)	0.0231 (4)
H14A	0.3865	0.1467	−0.1653	0.028*
C15A	0.13676 (19)	0.51169 (16)	0.37484 (17)	0.0153 (4)
C16A	−0.0638 (2)	0.4424 (2)	0.29854 (19)	0.0216 (4)
H16A	−0.1273	0.4980	0.3565	0.032*
H16B	−0.0431	0.3547	0.3411	0.032*
H16C	−0.1071	0.4334	0.2253	0.032*
C17A	0.40329 (19)	0.49855 (17)	0.15967 (18)	0.0173 (4)
H17A	0.4812	0.5430	0.1128	0.026*
H17B	0.4357	0.4064	0.1837	0.026*
H17C	0.3649	0.5441	0.2353	0.026*
C18A	0.6795 (3)	0.4372 (3)	−0.4251 (3)	0.0464 (7)
H18A	0.7407	0.4984	−0.4750	0.070*
H18B	0.6178	0.4102	−0.4777	0.070*
H18C	0.7354	0.3589	−0.3936	0.070*
C19A	0.2354 (2)	0.39371 (17)	0.55147 (17)	0.0169 (4)
H19A	0.2930	0.4673	0.5479	0.020*
H19B	0.2950	0.3098	0.5647	0.020*
C20A	0.1196 (2)	0.40578 (17)	0.66165 (18)	0.0164 (4)
C25A	0.0892 (2)	0.52025 (18)	0.72572 (19)	0.0215 (4)
H25A	0.1435	0.5919	0.7003	0.026*
C24A	−0.0185 (2)	0.53159 (19)	0.8256 (2)	0.0231 (4)
H24A	−0.0379	0.6101	0.8684	0.028*
C23A	−0.0973 (2)	0.4273 (2)	0.86241 (19)	0.0216 (4)
C22A	−0.0701 (2)	0.3119 (2)	0.8021 (2)	0.0257 (4)
H22A	−0.1250	0.2408	0.8281	0.031*
C21A	0.0390 (2)	0.30165 (18)	0.7025 (2)	0.0226 (4)
H21A	0.0592	0.2221	0.6615	0.027*
Cl1B	−0.41742 (5)	−0.15591 (6)	0.87240 (5)	0.03522 (14)
O2B	0.93434 (14)	−0.15643 (12)	−0.05692 (13)	0.0195 (3)
O1B	0.21426 (13)	0.10797 (12)	0.44275 (13)	0.0184 (3)
N1B	0.15706 (16)	−0.09932 (14)	0.44927 (16)	0.0164 (3)
H1BC	0.1836	−0.1845	0.4606	0.020*
C1B	0.57941 (19)	−0.24179 (17)	0.32933 (19)	0.0172 (4)
H1BA	0.6020	−0.2909	0.2530	0.021*
H1BB	0.6597	−0.2589	0.3748	0.021*
C2B	0.4529 (2)	−0.29311 (17)	0.41279 (19)	0.0180 (4)
H2BA	0.4746	−0.3881	0.4384	0.022*
H2BB	0.3750	−0.2845	0.3646	0.022*
C3B	0.4093 (2)	−0.21696 (17)	0.52968 (18)	0.0171 (4)
H3BA	0.4818	−0.2380	0.5839	0.021*
H3BB	0.3227	−0.2484	0.5770	0.021*
C4B	0.38536 (19)	−0.06473 (16)	0.50334 (18)	0.0145 (3)
C5B	0.51524 (18)	−0.01864 (16)	0.41259 (17)	0.0135 (3)
H5BA	0.5943	−0.0454	0.4600	0.016*
C6B	0.51584 (19)	0.13104 (17)	0.38311 (18)	0.0165 (4)
H6BA	0.4546	0.1627	0.3203	0.020*
H6BB	0.4803	0.1768	0.4602	0.020*
C7B	0.66360 (19)	0.16254 (17)	0.33197 (18)	0.0178 (4)
H7BA	0.6608	0.2563	0.2979	0.021*
H7BB	0.7179	0.1516	0.4019	0.021*
C8B	0.73655 (19)	0.07608 (16)	0.23043 (18)	0.0162 (4)
C9B	0.68902 (18)	−0.04533 (16)	0.21288 (17)	0.0144 (3)
C10B	0.55570 (18)	−0.09253 (16)	0.29044 (17)	0.0136 (3)
C11B	0.76029 (19)	−0.11839 (17)	0.11567 (18)	0.0157 (4)
H11B	0.7293	−0.1998	0.1033	0.019*
C12B	0.87536 (19)	−0.07576 (17)	0.03631 (18)	0.0167 (4)
C13B	0.9237 (2)	0.04185 (18)	0.05406 (19)	0.0198 (4)
H13B	1.0032	0.0714	0.0014	0.024*
C14B	0.8533 (2)	0.11528 (17)	0.15050 (19)	0.0192 (4)
H14B	0.8861	0.1960	0.1626	0.023*
C15B	0.24622 (18)	−0.01215 (16)	0.45988 (17)	0.0136 (3)
C16B	0.3739 (2)	−0.00538 (18)	0.63072 (18)	0.0187 (4)
H16D	0.3074	−0.0501	0.6934	0.028*
H16E	0.3423	0.0893	0.6215	0.028*
H16F	0.4649	−0.0177	0.6580	0.028*
C17B	0.44389 (19)	−0.06540 (17)	0.20453 (18)	0.0169 (4)
H17D	0.4708	−0.1187	0.1323	0.025*
H17E	0.4348	0.0287	0.1751	0.025*
H17F	0.3550	−0.0890	0.2516	0.025*
C18B	1.0448 (2)	−0.10871 (19)	−0.14677 (19)	0.0225 (4)
H18D	1.0694	−0.1680	−0.2146	0.034*
H18E	1.1256	−0.1059	−0.1058	0.034*
H18F	1.0150	−0.0196	−0.1815	0.034*
C19B	0.01822 (19)	−0.05750 (18)	0.41965 (19)	0.0181 (4)
H19C	0.0025	−0.1075	0.3507	0.022*
H19D	0.0112	0.0377	0.3904	0.022*
C20B	−0.09233 (19)	−0.08021 (18)	0.53241 (18)	0.0174 (4)
C21B	−0.1337 (2)	−0.20669 (19)	0.56702 (19)	0.0203 (4)
H21B	−0.0931	−0.2777	0.5180	0.024*
C22B	−0.2328 (2)	−0.2304 (2)	0.6717 (2)	0.0235 (4)
H22B	−0.2602	−0.3167	0.6943	0.028*
C23B	−0.2908 (2)	−0.1274 (2)	0.74192 (19)	0.0233 (4)
C24B	−0.2519 (2)	−0.0001 (2)	0.7116 (2)	0.0250 (4)
H24B	−0.2922	0.0702	0.7616	0.030*
C25B	−0.1530 (2)	0.02160 (19)	0.6066 (2)	0.0212 (4)
H25B	−0.1258	0.1081	0.5846	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1A	0.0203 (2)	0.0457 (3)	0.0272 (3)	0.0003 (2)	0.0034 (2)	0.0011 (2)
O2A	0.0372 (9)	0.0354 (8)	0.0270 (8)	−0.0038 (7)	0.0151 (7)	−0.0034 (7)
O1A	0.0197 (7)	0.0124 (5)	0.0202 (7)	−0.0025 (5)	−0.0023 (5)	−0.0022 (5)
N1A	0.0267 (9)	0.0123 (6)	0.0163 (8)	−0.0013 (6)	−0.0043 (7)	−0.0016 (6)
C1A	0.0178 (9)	0.0135 (7)	0.0171 (9)	−0.0018 (7)	−0.0004 (7)	0.0008 (7)
C2A	0.0180 (9)	0.0116 (7)	0.0201 (9)	0.0000 (7)	−0.0029 (7)	−0.0004 (7)
C3A	0.0143 (9)	0.0175 (8)	0.0183 (9)	0.0018 (7)	−0.0009 (7)	−0.0016 (7)
C4A	0.0143 (9)	0.0144 (7)	0.0163 (9)	−0.0031 (7)	0.0009 (7)	−0.0016 (7)
C5A	0.0122 (8)	0.0131 (7)	0.0149 (9)	−0.0016 (6)	−0.0008 (7)	−0.0018 (6)
C6A	0.0183 (9)	0.0126 (7)	0.0188 (9)	−0.0036 (7)	−0.0037 (7)	0.0004 (7)
C7A	0.0225 (10)	0.0142 (8)	0.0226 (10)	−0.0030 (7)	−0.0058 (8)	−0.0035 (7)
C8A	0.0167 (9)	0.0181 (8)	0.0167 (9)	0.0015 (7)	−0.0056 (7)	−0.0019 (7)
C9A	0.0132 (9)	0.0181 (8)	0.0174 (9)	0.0027 (7)	−0.0045 (7)	−0.0027 (7)
C10A	0.0115 (8)	0.0136 (7)	0.0161 (9)	−0.0019 (6)	−0.0003 (7)	0.0004 (7)
C11A	0.0187 (9)	0.0205 (8)	0.0222 (10)	−0.0012 (7)	0.0003 (8)	−0.0015 (8)
C12A	0.0187 (10)	0.0281 (10)	0.0205 (10)	0.0019 (8)	0.0013 (8)	−0.0004 (8)
C13A	0.0253 (11)	0.0277 (10)	0.0194 (10)	0.0072 (8)	−0.0032 (8)	−0.0076 (8)
C14A	0.0270 (11)	0.0204 (9)	0.0231 (10)	0.0035 (8)	−0.0092 (8)	−0.0064 (8)
C15A	0.0116 (8)	0.0151 (8)	0.0174 (9)	−0.0027 (7)	0.0023 (7)	0.0009 (7)
C16A	0.0153 (9)	0.0255 (9)	0.0230 (10)	−0.0071 (7)	0.0033 (8)	−0.0021 (8)
C17A	0.0135 (9)	0.0179 (8)	0.0206 (9)	−0.0028 (7)	−0.0010 (7)	−0.0031 (7)
C18A	0.0477 (17)	0.0441 (14)	0.0350 (14)	0.0056 (12)	0.0196 (12)	−0.0011 (11)
C19A	0.0162 (9)	0.0145 (8)	0.0196 (10)	0.0005 (7)	−0.0041 (7)	0.0001 (7)
C20A	0.0168 (9)	0.0168 (8)	0.0159 (9)	−0.0003 (7)	−0.0057 (7)	0.0006 (7)
C25A	0.0263 (11)	0.0156 (8)	0.0222 (10)	−0.0039 (7)	−0.0022 (8)	−0.0005 (7)
C24A	0.0266 (11)	0.0200 (8)	0.0225 (10)	−0.0004 (8)	−0.0040 (8)	−0.0036 (8)
C23A	0.0154 (9)	0.0304 (10)	0.0171 (9)	0.0011 (8)	−0.0024 (7)	0.0031 (8)
C22A	0.0245 (11)	0.0232 (9)	0.0297 (11)	−0.0079 (8)	−0.0027 (9)	0.0011 (8)
C21A	0.0243 (10)	0.0164 (8)	0.0284 (11)	−0.0047 (8)	−0.0052 (9)	−0.0029 (8)
Cl1B	0.0199 (3)	0.0615 (4)	0.0211 (3)	−0.0021 (2)	0.0003 (2)	0.0029 (2)
O2B	0.0149 (7)	0.0194 (6)	0.0231 (7)	−0.0036 (5)	0.0020 (5)	−0.0027 (5)
O1B	0.0154 (6)	0.0125 (5)	0.0270 (7)	−0.0002 (5)	−0.0047 (5)	0.0003 (5)
N1B	0.0107 (7)	0.0121 (6)	0.0266 (9)	−0.0016 (6)	−0.0041 (6)	0.0000 (6)
C1B	0.0145 (9)	0.0116 (7)	0.0248 (10)	−0.0017 (6)	−0.0008 (7)	−0.0013 (7)
C2B	0.0151 (9)	0.0114 (7)	0.0265 (10)	−0.0025 (6)	−0.0006 (7)	0.0001 (7)
C3B	0.0148 (9)	0.0133 (8)	0.0218 (10)	−0.0019 (7)	−0.0021 (7)	0.0050 (7)
C4B	0.0124 (9)	0.0126 (7)	0.0180 (9)	−0.0016 (6)	−0.0021 (7)	0.0005 (7)
C5B	0.0094 (8)	0.0126 (7)	0.0179 (9)	−0.0012 (6)	−0.0009 (7)	−0.0008 (7)
C6B	0.0132 (9)	0.0138 (7)	0.0226 (10)	−0.0021 (7)	−0.0016 (7)	−0.0027 (7)
C7B	0.0169 (9)	0.0138 (7)	0.0232 (10)	−0.0057 (7)	−0.0013 (7)	−0.0021 (7)
C8B	0.0131 (9)	0.0138 (8)	0.0219 (10)	−0.0015 (6)	−0.0042 (7)	−0.0009 (7)
C9B	0.0114 (8)	0.0140 (7)	0.0182 (9)	−0.0024 (6)	−0.0040 (7)	0.0008 (7)
C10B	0.0097 (8)	0.0121 (7)	0.0191 (9)	−0.0020 (6)	−0.0020 (7)	−0.0009 (7)
C11B	0.0122 (9)	0.0133 (7)	0.0220 (10)	−0.0012 (6)	−0.0048 (7)	−0.0007 (7)
C12B	0.0129 (9)	0.0181 (8)	0.0185 (9)	0.0005 (7)	−0.0030 (7)	−0.0001 (7)
C13B	0.0138 (9)	0.0187 (8)	0.0262 (11)	−0.0055 (7)	−0.0007 (7)	0.0016 (8)
C14B	0.0173 (9)	0.0144 (8)	0.0267 (10)	−0.0060 (7)	−0.0036 (8)	−0.0003 (7)
C15B	0.0126 (9)	0.0140 (7)	0.0139 (9)	−0.0018 (6)	−0.0005 (7)	−0.0013 (6)
C16B	0.0167 (9)	0.0200 (8)	0.0189 (10)	−0.0008 (7)	−0.0019 (7)	−0.0022 (7)
C17B	0.0128 (9)	0.0187 (8)	0.0198 (9)	−0.0023 (7)	−0.0030 (7)	−0.0027 (7)
C18B	0.0188 (10)	0.0239 (9)	0.0220 (10)	−0.0011 (8)	0.0023 (8)	0.0008 (8)
C19B	0.0131 (9)	0.0180 (8)	0.0233 (10)	−0.0008 (7)	−0.0046 (7)	0.0000 (7)
C20B	0.0109 (9)	0.0201 (8)	0.0223 (10)	−0.0012 (7)	−0.0066 (7)	−0.0010 (7)
C21B	0.0154 (9)	0.0202 (8)	0.0247 (10)	−0.0012 (7)	−0.0021 (8)	−0.0017 (8)
C22B	0.0173 (10)	0.0259 (9)	0.0272 (11)	−0.0035 (8)	−0.0048 (8)	0.0021 (8)
C23B	0.0118 (9)	0.0396 (11)	0.0173 (10)	0.0001 (8)	−0.0030 (7)	0.0019 (8)
C24B	0.0188 (10)	0.0292 (10)	0.0287 (11)	0.0039 (8)	−0.0082 (8)	−0.0112 (9)
C25B	0.0153 (9)	0.0201 (8)	0.0294 (11)	0.0002 (7)	−0.0073 (8)	−0.0036 (8)

Geometric parameters (Å, º) top

Cl1A—C23A	1.741 (2)	Cl1B—C23B	1.747 (2)
O2A—C12A	1.378 (3)	O2B—C12B	1.375 (2)
O2A—C18A	1.413 (3)	O2B—C18B	1.430 (2)
O1A—C15A	1.233 (2)	O1B—C15B	1.232 (2)
N1A—C15A	1.348 (2)	N1B—C15B	1.350 (2)
N1A—C19A	1.462 (3)	N1B—C19B	1.460 (2)
N1A—H1AC	0.8800	N1B—H1BC	0.8800
C1A—C2A	1.525 (3)	C1B—C2B	1.526 (3)
C1A—C10A	1.546 (2)	C1B—C10B	1.541 (2)
C1A—H1AA	0.9900	C1B—H1BA	0.9900
C1A—H1AB	0.9900	C1B—H1BB	0.9900
C2A—C3A	1.523 (3)	C2B—C3B	1.526 (3)
C2A—H2AA	0.9900	C2B—H2BA	0.9900
C2A—H2AB	0.9900	C2B—H2BB	0.9900
C3A—C4A	1.537 (2)	C3B—C4B	1.549 (2)
C3A—H3AA	0.9900	C3B—H3BA	0.9900
C3A—H3AB	0.9900	C3B—H3BB	0.9900
C4A—C15A	1.545 (3)	C4B—C15B	1.541 (2)
C4A—C16A	1.544 (3)	C4B—C16B	1.546 (3)
C4A—C5A	1.565 (2)	C4B—C5B	1.566 (2)
C5A—C6A	1.535 (2)	C5B—C6B	1.531 (2)
C5A—C10A	1.555 (2)	C5B—C10B	1.560 (2)
C5A—H5AA	1.0000	C5B—H5BA	1.0000
C6A—C7A	1.520 (3)	C6B—C7B	1.527 (2)
C6A—H6AA	0.9900	C6B—H6BA	0.9900
C6A—H6AB	0.9900	C6B—H6BB	0.9900
C7A—C8A	1.512 (3)	C7B—C8B	1.510 (3)
C7A—H7AA	0.9900	C7B—H7BA	0.9900
C7A—H7AB	0.9900	C7B—H7BB	0.9900
C8A—C14A	1.396 (3)	C8B—C14B	1.392 (3)
C8A—C9A	1.408 (2)	C8B—C9B	1.419 (2)
C9A—C11A	1.393 (3)	C9B—C11B	1.393 (3)
C9A—C10A	1.536 (3)	C9B—C10B	1.537 (2)
C10A—C17A	1.544 (3)	C10B—C17B	1.542 (2)
C11A—C12A	1.387 (3)	C11B—C12B	1.389 (3)
C11A—H11A	0.9500	C11B—H11B	0.9500
C12A—C13A	1.392 (3)	C12B—C13B	1.387 (3)
C13A—C14A	1.380 (3)	C13B—C14B	1.387 (3)
C13A—H13A	0.9500	C13B—H13B	0.9500
C14A—H14A	0.9500	C14B—H14B	0.9500
C16A—H16A	0.9800	C16B—H16D	0.9800
C16A—H16B	0.9800	C16B—H16E	0.9800
C16A—H16C	0.9800	C16B—H16F	0.9800
C17A—H17A	0.9800	C17B—H17D	0.9800
C17A—H17B	0.9800	C17B—H17E	0.9800
C17A—H17C	0.9800	C17B—H17F	0.9800
C18A—H18A	0.9800	C18B—H18D	0.9800
C18A—H18B	0.9800	C18B—H18E	0.9800
C18A—H18C	0.9800	C18B—H18F	0.9800
C19A—C20A	1.509 (3)	C19B—C20B	1.513 (3)
C19A—H19A	0.9900	C19B—H19C	0.9900
C19A—H19B	0.9900	C19B—H19D	0.9900
C20A—C25A	1.395 (3)	C20B—C25B	1.392 (3)
C20A—C21A	1.397 (3)	C20B—C21B	1.398 (3)
C25A—C24A	1.385 (3)	C21B—C22B	1.389 (3)
C25A—H25A	0.9500	C21B—H21B	0.9500
C24A—C23A	1.382 (3)	C22B—C23B	1.371 (3)
C24A—H24A	0.9500	C22B—H22B	0.9500
C23A—C22A	1.381 (3)	C23B—C24B	1.393 (3)
C22A—C21A	1.390 (3)	C24B—C25B	1.386 (3)
C22A—H22A	0.9500	C24B—H24B	0.9500
C21A—H21A	0.9500	C25B—H25B	0.9500

C12A—O2A—C18A	117.61 (19)	C23A—C24A—H24A	120.4
C15A—N1A—C19A	120.34 (15)	C25A—C24A—H24A	120.4
C5A—C4A—C15A	117.98 (15)	C22A—C23A—C24A	121.29 (19)
C5A—C4A—C16A	109.55 (15)	C22A—C23A—Cl1A	119.55 (16)
O2A—C12A—C11A	115.13 (19)	C24A—C23A—Cl1A	119.16 (16)
O2A—C12A—C13A	124.42 (19)	C23A—C22A—C21A	118.83 (18)
O1A—C15A—N1A	120.03 (17)	C23A—C22A—H22A	120.6
O1A—C15A—C4A	121.72 (15)	C21A—C22A—H22A	120.6
N1A—C15A—C4A	118.14 (15)	C22A—C21A—C20A	121.45 (18)
N1A—C19A—C20A	113.14 (16)	C22A—C21A—H21A	119.3
C12B—O2B—C18B	116.89 (14)	C20A—C21A—H21A	119.3
C15B—N1B—C19B	122.46 (15)	C15B—N1B—H1BC	118.8
C5B—C4B—C15B	113.92 (14)	C19B—N1B—H1BC	118.8
C5B—C4B—C16B	109.45 (14)	C2B—C1B—C10B	112.35 (15)
O2B—C12B—C13B	124.18 (17)	C2B—C1B—H1BA	109.1
O2B—C12B—C11B	115.91 (16)	C10B—C1B—H1BA	109.1
C11B—C12B—C13B	119.91 (17)	C2B—C1B—H1BB	109.1
O1B—C15B—N1B	120.97 (16)	C10B—C1B—H1BB	109.1
O1B—C15B—C4B	120.05 (16)	H1BA—C1B—H1BB	107.9
N1B—C15B—C4B	118.83 (15)	C1B—C2B—C3B	111.51 (15)
N1B—C19B—C20B	111.61 (15)	C1B—C2B—H2BA	109.3
C15A—N1A—H1AC	119.8	C3B—C2B—H2BA	109.3
C19A—N1A—H1AC	119.8	C1B—C2B—H2BB	109.3
C2A—C1A—C10A	112.96 (15)	C3B—C2B—H2BB	109.3
C2A—C1A—H1AA	109.0	H2BA—C2B—H2BB	108.0
C10A—C1A—H1AA	109.0	C2B—C3B—C4B	114.76 (15)
C2A—C1A—H1AB	109.0	C2B—C3B—H3BA	108.6
C10A—C1A—H1AB	109.0	C4B—C3B—H3BA	108.6
H1AA—C1A—H1AB	107.8	C2B—C3B—H3BB	108.6
C3A—C2A—C1A	110.85 (15)	C4B—C3B—H3BB	108.6
C3A—C2A—H2AA	109.5	H3BA—C3B—H3BB	107.6
C1A—C2A—H2AA	109.5	C15B—C4B—C16B	103.29 (14)
C3A—C2A—H2AB	109.5	C15B—C4B—C3B	115.10 (15)
C1A—C2A—H2AB	109.5	C16B—C4B—C3B	106.61 (15)
H2AA—C2A—H2AB	108.1	C3B—C4B—C5B	108.04 (14)
C2A—C3A—C4A	112.94 (15)	C6B—C5B—C10B	111.02 (14)
C2A—C3A—H3AA	109.0	C6B—C5B—C4B	115.85 (14)
C4A—C3A—H3AA	109.0	C10B—C5B—C4B	114.71 (14)
C2A—C3A—H3AB	109.0	C6B—C5B—H5BA	104.6
C4A—C3A—H3AB	109.0	C10B—C5B—H5BA	104.6
H3AA—C3A—H3AB	107.8	C4B—C5B—H5BA	104.6
C3A—C4A—C16A	107.06 (15)	C7B—C6B—C5B	109.38 (14)
C3A—C4A—C15A	108.79 (14)	C7B—C6B—H6BA	109.8
C16A—C4A—C15A	106.20 (15)	C5B—C6B—H6BA	109.8
C3A—C4A—C5A	106.79 (14)	C7B—C6B—H6BB	109.8
C6A—C5A—C10A	110.59 (14)	C5B—C6B—H6BB	109.8
C6A—C5A—C4A	116.89 (15)	H6BA—C6B—H6BB	108.2
C10A—C5A—C4A	115.51 (14)	C8B—C7B—C6B	113.42 (14)
C6A—C5A—H5AA	104.0	C8B—C7B—H7BA	108.9
C10A—C5A—H5AA	104.0	C6B—C7B—H7BA	108.9
C4A—C5A—H5AA	104.0	C8B—C7B—H7BB	108.9
C7A—C6A—C5A	107.99 (15)	C6B—C7B—H7BB	108.9
C7A—C6A—H6AA	110.1	H7BA—C7B—H7BB	107.7
C5A—C6A—H6AA	110.1	C14B—C8B—C9B	118.25 (17)
C7A—C6A—H6AB	110.1	C14B—C8B—C7B	119.96 (15)
C5A—C6A—H6AB	110.1	C9B—C8B—C7B	121.79 (16)
H6AA—C6A—H6AB	108.4	C11B—C9B—C8B	118.43 (16)
C8A—C7A—C6A	112.30 (15)	C11B—C9B—C10B	119.28 (15)
C8A—C7A—H7AA	109.1	C8B—C9B—C10B	122.11 (16)
C6A—C7A—H7AA	109.1	C9B—C10B—C1B	109.87 (14)
C8A—C7A—H7AB	109.1	C9B—C10B—C17B	106.34 (14)
C6A—C7A—H7AB	109.1	C1B—C10B—C17B	110.19 (14)
H7AA—C7A—H7AB	107.9	C9B—C10B—C5B	110.09 (14)
C14A—C8A—C9A	118.90 (18)	C1B—C10B—C5B	107.83 (14)
C14A—C8A—C7A	119.17 (17)	C17B—C10B—C5B	112.52 (14)
C9A—C8A—C7A	121.87 (17)	C12B—C11B—C9B	121.99 (16)
C11A—C9A—C8A	118.31 (17)	C12B—C11B—H11B	119.0
C11A—C9A—C10A	119.33 (16)	C9B—C11B—H11B	119.0
C8A—C9A—C10A	122.28 (17)	C14B—C13B—C12B	118.47 (17)
C9A—C10A—C17A	107.25 (14)	C14B—C13B—H13B	120.8
C9A—C10A—C1A	109.66 (14)	C12B—C13B—H13B	120.8
C17A—C10A—C1A	109.66 (14)	C13B—C14B—C8B	122.94 (16)
C9A—C10A—C5A	109.03 (14)	C13B—C14B—H14B	118.5
C17A—C10A—C5A	113.12 (15)	C8B—C14B—H14B	118.5
C1A—C10A—C5A	108.09 (14)	C4B—C16B—H16D	109.5
C12A—C11A—C9A	121.63 (18)	C4B—C16B—H16E	109.5
C12A—C11A—H11A	119.2	H16D—C16B—H16E	109.5
C9A—C11A—H11A	119.2	C4B—C16B—H16F	109.5
C11A—C12A—C13A	120.4 (2)	H16D—C16B—H16F	109.5
C14A—C13A—C12A	118.01 (19)	H16E—C16B—H16F	109.5
C14A—C13A—H13A	121.0	C10B—C17B—H17D	109.5
C12A—C13A—H13A	121.0	C10B—C17B—H17E	109.5
C13A—C14A—C8A	122.68 (18)	H17D—C17B—H17E	109.5
C13A—C14A—H14A	118.7	C10B—C17B—H17F	109.5
C8A—C14A—H14A	118.7	H17D—C17B—H17F	109.5
C4A—C16A—H16A	109.5	H17E—C17B—H17F	109.5
C4A—C16A—H16B	109.5	O2B—C18B—H18D	109.5
H16A—C16A—H16B	109.5	O2B—C18B—H18E	109.5
C4A—C16A—H16C	109.5	H18D—C18B—H18E	109.5
H16A—C16A—H16C	109.5	O2B—C18B—H18F	109.5
H16B—C16A—H16C	109.5	H18D—C18B—H18F	109.5
C10A—C17A—H17A	109.5	H18E—C18B—H18F	109.5
C10A—C17A—H17B	109.5	N1B—C19B—H19C	109.3
H17A—C17A—H17B	109.5	C20B—C19B—H19C	109.3
C10A—C17A—H17C	109.5	N1B—C19B—H19D	109.3
H17A—C17A—H17C	109.5	C20B—C19B—H19D	109.3
H17B—C17A—H17C	109.5	H19C—C19B—H19D	108.0
O2A—C18A—H18A	109.5	C25B—C20B—C21B	118.03 (18)
O2A—C18A—H18B	109.5	C25B—C20B—C19B	121.73 (16)
H18A—C18A—H18B	109.5	C21B—C20B—C19B	120.22 (17)
O2A—C18A—H18C	109.5	C22B—C21B—C20B	121.21 (18)
H18A—C18A—H18C	109.5	C22B—C21B—H21B	119.4
H18B—C18A—H18C	109.5	C20B—C21B—H21B	119.4
N1A—C19A—H19A	109.0	C23B—C22B—C21B	119.04 (18)
C20A—C19A—H19A	109.0	C23B—C22B—H22B	120.5
N1A—C19A—H19B	109.0	C21B—C22B—H22B	120.5
C20A—C19A—H19B	109.0	C22B—C23B—C24B	121.71 (19)
H19A—C19A—H19B	107.8	C22B—C23B—Cl1B	119.33 (16)
C25A—C20A—C21A	117.87 (18)	C24B—C23B—Cl1B	118.96 (17)
C25A—C20A—C19A	121.56 (17)	C25B—C24B—C23B	118.36 (19)
C21A—C20A—C19A	120.57 (17)	C25B—C24B—H24B	120.8
C24A—C25A—C20A	121.35 (18)	C23B—C24B—H24B	120.8
C24A—C25A—H25A	119.3	C24B—C25B—C20B	121.65 (18)
C20A—C25A—H25A	119.3	C24B—C25B—H25B	119.2
C23A—C24A—C25A	119.20 (18)	C20B—C25B—H25B	119.2

C10A—C1A—C2A—C3A	−56.6 (2)	C10B—C1B—C2B—C3B	−56.4 (2)
C1A—C2A—C3A—C4A	58.8 (2)	C1B—C2B—C3B—C4B	53.6 (2)
C2A—C3A—C4A—C16A	−173.31 (16)	C2B—C3B—C4B—C15B	78.1 (2)
C2A—C3A—C4A—C15A	72.32 (19)	C2B—C3B—C4B—C16B	−168.01 (15)
C2A—C3A—C4A—C5A	−56.0 (2)	C2B—C3B—C4B—C5B	−50.5 (2)
C3A—C4A—C5A—C6A	−172.10 (15)	C15B—C4B—C5B—C6B	55.2 (2)
C16A—C4A—C5A—C6A	−56.5 (2)	C16B—C4B—C5B—C6B	−59.88 (19)
C15A—C4A—C5A—C6A	65.1 (2)	C3B—C4B—C5B—C6B	−175.58 (16)
C3A—C4A—C5A—C10A	55.14 (19)	C15B—C4B—C5B—C10B	−76.25 (18)
C16A—C4A—C5A—C10A	170.76 (15)	C16B—C4B—C5B—C10B	168.70 (14)
C15A—C4A—C5A—C10A	−67.6 (2)	C3B—C4B—C5B—C10B	53.00 (19)
C10A—C5A—C6A—C7A	−68.57 (19)	C10B—C5B—C6B—C7B	−65.47 (19)
C4A—C5A—C6A—C7A	156.49 (15)	C4B—C5B—C6B—C7B	161.40 (15)
C5A—C6A—C7A—C8A	51.1 (2)	C5B—C6B—C7B—C8B	47.7 (2)
C6A—C7A—C8A—C14A	160.80 (17)	C6B—C7B—C8B—C14B	161.61 (17)
C6A—C7A—C8A—C9A	−21.7 (2)	C6B—C7B—C8B—C9B	−18.0 (2)
C14A—C8A—C9A—C11A	0.7 (3)	C14B—C8B—C9B—C11B	−0.8 (2)
C7A—C8A—C9A—C11A	−176.79 (17)	C7B—C8B—C9B—C11B	178.80 (17)
C14A—C8A—C9A—C10A	−176.05 (17)	C14B—C8B—C9B—C10B	−175.83 (17)
C7A—C8A—C9A—C10A	6.5 (3)	C7B—C8B—C9B—C10B	3.8 (3)
C11A—C9A—C10A—C17A	−74.8 (2)	C11B—C9B—C10B—C1B	47.1 (2)
C8A—C9A—C10A—C17A	101.95 (18)	C8B—C9B—C10B—C1B	−137.98 (17)
C11A—C9A—C10A—C1A	44.2 (2)	C11B—C9B—C10B—C17B	−72.18 (18)
C8A—C9A—C10A—C1A	−139.03 (17)	C8B—C9B—C10B—C17B	102.79 (18)
C11A—C9A—C10A—C5A	162.40 (16)	C11B—C9B—C10B—C5B	165.67 (15)
C8A—C9A—C10A—C5A	−20.9 (2)	C8B—C9B—C10B—C5B	−19.4 (2)
C2A—C1A—C10A—C9A	171.62 (15)	C2B—C1B—C10B—C9B	176.86 (16)
C2A—C1A—C10A—C17A	−70.86 (19)	C2B—C1B—C10B—C17B	−66.3 (2)
C2A—C1A—C10A—C5A	52.9 (2)	C2B—C1B—C10B—C5B	56.86 (19)
C6A—C5A—C10A—C9A	51.41 (19)	C6B—C5B—C10B—C9B	49.73 (19)
C4A—C5A—C10A—C9A	−172.98 (14)	C4B—C5B—C10B—C9B	−176.57 (13)
C6A—C5A—C10A—C17A	−67.82 (19)	C6B—C5B—C10B—C1B	169.59 (14)
C4A—C5A—C10A—C17A	67.79 (19)	C4B—C5B—C10B—C1B	−56.71 (18)
C6A—C5A—C10A—C1A	170.55 (15)	C6B—C5B—C10B—C17B	−68.69 (18)
C4A—C5A—C10A—C1A	−53.8 (2)	C4B—C5B—C10B—C17B	65.01 (18)
C8A—C9A—C11A—C12A	0.3 (3)	C8B—C9B—C11B—C12B	−0.1 (3)
C10A—C9A—C11A—C12A	177.15 (18)	C10B—C9B—C11B—C12B	175.09 (16)
C18A—O2A—C12A—C11A	174.5 (2)	C18B—O2B—C12B—C13B	−5.6 (3)
C18A—O2A—C12A—C13A	−5.2 (3)	C18B—O2B—C12B—C11B	174.36 (15)
C9A—C11A—C12A—O2A	179.21 (18)	C9B—C11B—C12B—O2B	−178.96 (16)
C9A—C11A—C12A—C13A	−1.1 (3)	C9B—C11B—C12B—C13B	1.0 (3)
O2A—C12A—C13A—C14A	−179.5 (2)	O2B—C12B—C13B—C14B	178.92 (17)
C11A—C12A—C13A—C14A	0.8 (3)	C11B—C12B—C13B—C14B	−1.1 (3)
C12A—C13A—C14A—C8A	0.2 (3)	C12B—C13B—C14B—C8B	0.2 (3)
C9A—C8A—C14A—C13A	−1.0 (3)	C9B—C8B—C14B—C13B	0.8 (3)
C7A—C8A—C14A—C13A	176.58 (18)	C7B—C8B—C14B—C13B	−178.85 (18)
C19A—N1A—C15A—O1A	2.5 (3)	C19B—N1B—C15B—O1B	−1.2 (3)
C19A—N1A—C15A—C4A	−173.81 (16)	C19B—N1B—C15B—C4B	174.41 (17)
C3A—C4A—C15A—O1A	7.0 (2)	C16B—C4B—C15B—O1B	60.5 (2)
C16A—C4A—C15A—O1A	−107.93 (19)	C3B—C4B—C15B—O1B	176.27 (17)
C5A—C4A—C15A—O1A	128.77 (18)	C5B—C4B—C15B—O1B	−58.1 (2)
C3A—C4A—C15A—N1A	−176.73 (16)	C16B—C4B—C15B—N1B	−115.15 (17)
C16A—C4A—C15A—N1A	68.3 (2)	C3B—C4B—C15B—N1B	0.6 (2)
C5A—C4A—C15A—N1A	−55.0 (2)	C5B—C4B—C15B—N1B	126.22 (17)
C15A—N1A—C19A—C20A	77.5 (2)	C15B—N1B—C19B—C20B	−107.94 (19)
N1A—C19A—C20A—C25A	−109.09 (19)	N1B—C19B—C20B—C25B	98.92 (19)
N1A—C19A—C20A—C21A	70.8 (2)	N1B—C19B—C20B—C21B	−79.2 (2)
C21A—C20A—C25A—C24A	−0.9 (3)	C25B—C20B—C21B—C22B	0.4 (3)
C19A—C20A—C25A—C24A	179.07 (18)	C19B—C20B—C21B—C22B	178.64 (18)
C20A—C25A—C24A—C23A	0.0 (3)	C20B—C21B—C22B—C23B	0.0 (3)
C25A—C24A—C23A—C22A	0.5 (3)	C21B—C22B—C23B—C24B	−0.5 (3)
C25A—C24A—C23A—Cl1A	−178.89 (15)	C21B—C22B—C23B—Cl1B	179.07 (15)
C24A—C23A—C22A—C21A	0.0 (3)	C22B—C23B—C24B—C25B	0.7 (3)
Cl1A—C23A—C22A—C21A	179.38 (15)	Cl1B—C23B—C24B—C25B	−178.92 (15)
C23A—C22A—C21A—C20A	−1.0 (3)	C23B—C24B—C25B—C20B	−0.3 (3)
C25A—C20A—C21A—C22A	1.4 (3)	C21B—C20B—C25B—C24B	−0.3 (3)
C19A—C20A—C21A—C22A	−178.57 (18)	C19B—C20B—C25B—C24B	−178.45 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1AC···O1B	0.88	2.19	2.9154 (19)	140
N1B—H1BC···O1Aⁱ	0.88	2.23	2.9802 (19)	143

Symmetry code: (i) x, y−1, z.

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