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], C
25H
30ClNO
2, 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.
Supporting information
CCDC reference: 624998
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
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,9,10,10
a-
octahydrophenanthrene-1-carboxamide
top
Crystal data top
C25H30ClNO2 | Z = 2 |
Mr = 411.95 | F(000) = 440 |
Triclinic, P1 | Dx = 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 | Rint = 0.041 |
φ and ω scans | θmax = 28.2°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→13 |
Tmin = 0.878, Tmax = 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(Fo2) + (0.0716P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.002 |
6817 reflections | Δρmax = 0.37 e Å−3 |
529 parameters | Δρmin = −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 | Uiso*/Ueq | |
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. |