Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804008670/lh6200sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804008670/lh62003sup2.hkl |
CCDC reference: 239253
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 2000) and XPREP (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
C21H24ClNO3 | F(000) = 1584 |
Mr = 373.86 | Dx = 1.372 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 7584 reflections |
a = 7.7262 (4) Å | θ = 2.7–26.7° |
b = 19.8316 (10) Å | µ = 0.23 mm−1 |
c = 23.6182 (13) Å | T = 103 K |
V = 3618.8 (3) Å3 | Plate, colorless |
Z = 8 | 0.35 × 0.23 × 0.02 mm |
Bruker SMART 1000 CCD diffractometer | 8828 independent reflections |
Radiation source: sealed tube | 5974 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.079 |
φ and ω scans | θmax = 28.4°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −10→10 |
Tmin = 0.839, Tmax = 0.995 | k = −26→26 |
29542 measured reflections | l = −28→30 |
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)] = 0.054 | H-atom parameters constrained |
wR(F2) = 0.121 | w = 1/[σ2(Fo2) + (0.0274P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.23 | (Δ/σ)max < 0.001 |
8828 reflections | Δρmax = 0.29 e Å−3 |
475 parameters | Δρmin = −0.28 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 3864 Friedels |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.02 (6) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.3453 (4) | 1.01205 (14) | 0.26310 (13) | 0.0214 (7) | |
H1A | 0.2312 | 1.0298 | 0.2636 | 0.026* | |
C2 | 0.4820 (4) | 1.05050 (14) | 0.28520 (14) | 0.0217 (7) | |
H2A | 0.4597 | 1.0949 | 0.2985 | 0.026* | |
C3 | 0.6508 (4) | 1.02479 (14) | 0.28800 (13) | 0.0209 (7) | |
O3 | 0.7894 (3) | 1.05602 (10) | 0.31354 (10) | 0.0306 (6) | |
C3A | 0.7517 (5) | 1.11304 (17) | 0.34922 (17) | 0.0433 (11) | |
H3AA | 0.8564 | 1.1263 | 0.3698 | 0.065* | |
H3AB | 0.6609 | 1.1008 | 0.3763 | 0.065* | |
H3AC | 0.7120 | 1.1508 | 0.3258 | 0.065* | |
C4 | 0.6787 (4) | 0.96135 (14) | 0.26409 (13) | 0.0192 (7) | |
O5 | 0.8276 (3) | 0.92333 (9) | 0.26977 (9) | 0.0229 (5) | |
C5 | 0.7845 (4) | 0.85433 (13) | 0.25050 (13) | 0.0185 (7) | |
H5A | 0.8728 | 0.8385 | 0.2225 | 0.022* | |
C6 | 0.7776 (4) | 0.80540 (14) | 0.30144 (13) | 0.0187 (7) | |
O6 | 0.9451 (3) | 0.80787 (10) | 0.32591 (9) | 0.0249 (5) | |
C6A | 0.9752 (5) | 0.76387 (17) | 0.37266 (15) | 0.0343 (9) | |
H6AA | 1.0825 | 0.7770 | 0.3919 | 0.051* | |
H6AB | 0.9856 | 0.7174 | 0.3590 | 0.051* | |
H6AC | 0.8782 | 0.7670 | 0.3993 | 0.051* | |
C19 | 0.6274 (4) | 0.82582 (14) | 0.33952 (14) | 0.0232 (7) | |
H19A | 0.6426 | 0.8368 | 0.3784 | 0.028* | |
C18 | 0.4740 (4) | 0.82718 (14) | 0.31447 (14) | 0.0203 (7) | |
H18A | 0.3710 | 0.8384 | 0.3343 | 0.024* | |
C9 | 0.2992 (4) | 0.82124 (14) | 0.22128 (13) | 0.0197 (7) | |
H9A | 0.2121 | 0.7905 | 0.2390 | 0.024* | |
C10 | 0.2325 (4) | 0.89536 (14) | 0.22914 (14) | 0.0228 (7) | |
H10A | 0.1683 | 0.9088 | 0.1947 | 0.027* | |
H10B | 0.1500 | 0.8963 | 0.2612 | 0.027* | |
C11 | 0.3751 (4) | 0.94744 (14) | 0.24025 (13) | 0.0178 (7) | |
C12 | 0.5450 (4) | 0.92669 (14) | 0.23801 (14) | 0.0187 (7) | |
C13 | 0.6061 (4) | 0.85717 (13) | 0.22250 (12) | 0.0163 (7) | |
C14 | 0.4740 (4) | 0.80950 (14) | 0.25175 (13) | 0.0168 (7) | |
C15 | 0.6159 (4) | 0.84450 (14) | 0.15829 (13) | 0.0196 (7) | |
H15A | 0.6887 | 0.8798 | 0.1407 | 0.024* | |
H15B | 0.6724 | 0.8004 | 0.1515 | 0.024* | |
C16 | 0.4401 (4) | 0.84459 (15) | 0.13038 (14) | 0.0231 (8) | |
H16A | 0.3937 | 0.8911 | 0.1296 | 0.028* | |
H16B | 0.4511 | 0.8286 | 0.0908 | 0.028* | |
N17 | 0.3200 (3) | 0.80043 (12) | 0.16154 (10) | 0.0201 (6) | |
C17A | 0.1547 (4) | 0.79408 (16) | 0.13129 (14) | 0.0289 (8) | |
H17A | 0.0756 | 0.7657 | 0.1533 | 0.043* | |
H17B | 0.1748 | 0.7734 | 0.0942 | 0.043* | |
H17C | 0.1034 | 0.8389 | 0.1262 | 0.043* | |
C8 | 0.5457 (4) | 0.73639 (14) | 0.24799 (14) | 0.0195 (7) | |
H8A | 0.5626 | 0.7235 | 0.2079 | 0.023* | |
H8B | 0.4626 | 0.7044 | 0.2653 | 0.023* | |
C7 | 0.7217 (4) | 0.73363 (15) | 0.28017 (13) | 0.0231 (7) | |
H7A | 0.7046 | 0.7047 | 0.3144 | 0.028* | |
Cl7 | 0.88774 (11) | 0.69438 (4) | 0.23736 (4) | 0.0290 (2) | |
C1' | 0.3035 (4) | 0.63333 (15) | −0.01950 (13) | 0.0264 (8) | |
H1'A | 0.1898 | 0.6513 | −0.0221 | 0.032* | |
C2' | 0.4351 (4) | 0.67291 (16) | 0.00153 (14) | 0.0276 (8) | |
H2'A | 0.4113 | 0.7186 | 0.0109 | 0.033* | |
C3' | 0.6031 (4) | 0.64793 (14) | 0.00964 (13) | 0.0242 (8) | |
O3' | 0.7286 (3) | 0.68907 (11) | 0.03239 (11) | 0.0386 (6) | |
C3A' | 0.7855 (7) | 0.6719 (2) | 0.0850 (2) | 0.0688 (15) | |
H3AD | 0.8723 | 0.7047 | 0.0976 | 0.103* | |
H3AE | 0.8373 | 0.6269 | 0.0837 | 0.103* | |
H3AF | 0.6877 | 0.6719 | 0.1114 | 0.103* | |
C4' | 0.6345 (4) | 0.58206 (14) | −0.00769 (13) | 0.0205 (7) | |
O5' | 0.7801 (3) | 0.54427 (9) | 0.00406 (10) | 0.0250 (5) | |
C5' | 0.7397 (4) | 0.47374 (14) | −0.01115 (13) | 0.0217 (7) | |
H5'A | 0.8336 | 0.4553 | −0.0358 | 0.026* | |
C6' | 0.7163 (4) | 0.42760 (15) | 0.04121 (14) | 0.0230 (7) | |
O6' | 0.8677 (3) | 0.41683 (11) | 0.07436 (10) | 0.0343 (6) | |
C6A' | 0.9321 (4) | 0.47280 (17) | 0.10669 (16) | 0.0352 (9) | |
H6AD | 1.0174 | 0.4566 | 0.1342 | 0.053* | |
H6AE | 0.8359 | 0.4945 | 0.1267 | 0.053* | |
H6AF | 0.9869 | 0.5054 | 0.0812 | 0.053* | |
C19' | 0.5581 (4) | 0.45030 (14) | 0.07372 (14) | 0.0226 (8) | |
H19C | 0.5637 | 0.4629 | 0.1125 | 0.027* | |
C18' | 0.4121 (4) | 0.45151 (14) | 0.04488 (13) | 0.0189 (7) | |
H18B | 0.3052 | 0.4649 | 0.0613 | 0.023* | |
C9' | 0.2611 (4) | 0.43979 (15) | −0.05240 (13) | 0.0225 (8) | |
H9'A | 0.1690 | 0.4106 | −0.0355 | 0.027* | |
C10' | 0.1956 (4) | 0.51514 (15) | −0.04908 (14) | 0.0238 (8) | |
H10C | 0.1390 | 0.5267 | −0.0854 | 0.029* | |
H10D | 0.1067 | 0.5183 | −0.0190 | 0.029* | |
C11' | 0.3350 (4) | 0.56691 (14) | −0.03721 (13) | 0.0200 (7) | |
C12' | 0.5054 (4) | 0.54565 (13) | −0.03430 (13) | 0.0173 (7) | |
C13' | 0.5671 (4) | 0.47506 (14) | −0.04456 (13) | 0.0184 (7) | |
C14' | 0.4275 (4) | 0.42980 (14) | −0.01690 (13) | 0.0186 (7) | |
C15' | 0.5923 (4) | 0.45809 (15) | −0.10842 (13) | 0.0233 (7) | |
H15C | 0.6702 | 0.4920 | −0.1257 | 0.028* | |
H15D | 0.6484 | 0.4134 | −0.1119 | 0.028* | |
C16' | 0.4218 (4) | 0.45723 (16) | −0.14062 (14) | 0.0281 (8) | |
H16C | 0.3760 | 0.5037 | −0.1439 | 0.034* | |
H16D | 0.4406 | 0.4394 | −0.1793 | 0.034* | |
N17' | 0.2960 (4) | 0.41443 (12) | −0.11032 (11) | 0.0266 (7) | |
C17' | 0.1367 (5) | 0.40576 (18) | −0.14414 (16) | 0.0414 (10) | |
H17D | 0.0565 | 0.3761 | −0.1239 | 0.062* | |
H17E | 0.1660 | 0.3857 | −0.1808 | 0.062* | |
H17F | 0.0821 | 0.4498 | −0.1501 | 0.062* | |
C8' | 0.4950 (4) | 0.35635 (14) | −0.01481 (14) | 0.0248 (8) | |
H8'A | 0.5152 | 0.3394 | −0.0537 | 0.030* | |
H8'B | 0.4087 | 0.3268 | 0.0038 | 0.030* | |
C7' | 0.6662 (4) | 0.35612 (14) | 0.01909 (14) | 0.0251 (8) | |
H7'A | 0.6492 | 0.3264 | 0.0528 | 0.030* | |
Cl7' | 0.84244 (12) | 0.32010 (4) | −0.02329 (4) | 0.0355 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0193 (17) | 0.0215 (15) | 0.0233 (18) | 0.0049 (13) | 0.0011 (16) | 0.0035 (14) |
C2 | 0.0305 (18) | 0.0113 (14) | 0.0232 (19) | 0.0021 (14) | −0.0019 (16) | 0.0001 (13) |
C3 | 0.0262 (18) | 0.0142 (14) | 0.0224 (17) | −0.0049 (14) | −0.0040 (16) | 0.0006 (12) |
O3 | 0.0307 (13) | 0.0185 (11) | 0.0425 (16) | 0.0009 (10) | −0.0122 (12) | −0.0070 (10) |
C3A | 0.048 (2) | 0.0250 (19) | 0.057 (3) | 0.0056 (17) | −0.019 (2) | −0.0190 (17) |
C4 | 0.0155 (15) | 0.0192 (15) | 0.0229 (18) | −0.0005 (13) | 0.0031 (15) | 0.0050 (13) |
O5 | 0.0189 (11) | 0.0153 (10) | 0.0346 (14) | 0.0016 (9) | −0.0063 (11) | −0.0027 (9) |
C5 | 0.0208 (16) | 0.0123 (13) | 0.0224 (18) | −0.0022 (12) | −0.0015 (15) | −0.0006 (12) |
C6 | 0.0204 (16) | 0.0194 (15) | 0.0164 (17) | −0.0003 (14) | −0.0031 (14) | −0.0008 (13) |
O6 | 0.0242 (12) | 0.0244 (12) | 0.0259 (13) | 0.0002 (10) | −0.0072 (10) | 0.0071 (10) |
C6A | 0.036 (2) | 0.0329 (19) | 0.034 (2) | 0.0056 (17) | −0.0052 (19) | 0.0088 (16) |
C19 | 0.0332 (19) | 0.0181 (15) | 0.0181 (17) | −0.0010 (15) | 0.0014 (17) | 0.0022 (13) |
C18 | 0.0243 (17) | 0.0147 (15) | 0.0220 (19) | −0.0035 (13) | 0.0057 (16) | 0.0008 (13) |
C9 | 0.0201 (16) | 0.0207 (15) | 0.0183 (17) | −0.0045 (14) | 0.0008 (14) | −0.0014 (13) |
C10 | 0.0196 (16) | 0.0222 (16) | 0.027 (2) | 0.0006 (13) | 0.0023 (16) | −0.0008 (14) |
C11 | 0.0176 (15) | 0.0181 (14) | 0.0177 (17) | −0.0021 (13) | 0.0005 (15) | 0.0016 (13) |
C12 | 0.0222 (17) | 0.0147 (14) | 0.0191 (17) | 0.0003 (13) | −0.0003 (15) | 0.0001 (13) |
C13 | 0.0187 (15) | 0.0144 (13) | 0.0159 (17) | 0.0005 (13) | −0.0009 (15) | −0.0010 (12) |
C14 | 0.0197 (16) | 0.0128 (14) | 0.0180 (18) | −0.0005 (12) | 0.0010 (14) | −0.0002 (12) |
C15 | 0.0243 (17) | 0.0166 (15) | 0.0179 (17) | −0.0041 (13) | 0.0025 (16) | 0.0017 (12) |
C16 | 0.0271 (18) | 0.0212 (16) | 0.0210 (18) | −0.0032 (14) | −0.0042 (16) | 0.0019 (13) |
N17 | 0.0203 (14) | 0.0232 (13) | 0.0167 (14) | −0.0068 (12) | −0.0023 (12) | 0.0007 (11) |
C17A | 0.0276 (18) | 0.0307 (18) | 0.029 (2) | −0.0068 (16) | −0.0056 (17) | −0.0015 (15) |
C8 | 0.0238 (17) | 0.0151 (14) | 0.0196 (18) | −0.0011 (13) | −0.0020 (15) | 0.0044 (12) |
C7 | 0.0303 (18) | 0.0162 (15) | 0.0227 (19) | 0.0014 (14) | 0.0025 (16) | 0.0024 (13) |
Cl7 | 0.0315 (5) | 0.0209 (4) | 0.0348 (5) | 0.0048 (4) | 0.0053 (4) | −0.0031 (4) |
C1' | 0.0321 (19) | 0.0255 (16) | 0.0215 (19) | 0.0111 (15) | −0.0051 (17) | −0.0009 (14) |
C2' | 0.043 (2) | 0.0183 (15) | 0.0212 (19) | 0.0049 (15) | −0.0039 (17) | 0.0006 (14) |
C3' | 0.035 (2) | 0.0168 (15) | 0.0206 (18) | −0.0106 (15) | −0.0038 (17) | 0.0023 (13) |
O3' | 0.0510 (16) | 0.0267 (12) | 0.0382 (16) | −0.0178 (12) | −0.0134 (14) | −0.0017 (11) |
C3A' | 0.097 (4) | 0.039 (2) | 0.070 (3) | −0.026 (2) | −0.047 (3) | −0.002 (2) |
C4' | 0.0242 (18) | 0.0184 (14) | 0.0190 (17) | −0.0003 (14) | −0.0019 (15) | 0.0047 (13) |
O5' | 0.0206 (12) | 0.0189 (10) | 0.0354 (14) | −0.0017 (9) | −0.0039 (11) | −0.0034 (9) |
C5' | 0.0200 (17) | 0.0168 (14) | 0.0281 (19) | −0.0001 (13) | −0.0034 (16) | −0.0027 (14) |
C6' | 0.0234 (18) | 0.0190 (15) | 0.0266 (19) | 0.0013 (14) | −0.0074 (16) | −0.0022 (14) |
O6' | 0.0370 (15) | 0.0299 (13) | 0.0358 (15) | 0.0076 (11) | −0.0192 (13) | −0.0053 (11) |
C6A' | 0.029 (2) | 0.039 (2) | 0.037 (2) | 0.0002 (16) | −0.0091 (18) | −0.0084 (17) |
C19' | 0.036 (2) | 0.0147 (15) | 0.0174 (18) | −0.0008 (14) | −0.0026 (16) | 0.0005 (13) |
C18' | 0.0249 (18) | 0.0163 (15) | 0.0155 (17) | −0.0005 (13) | 0.0002 (15) | 0.0002 (12) |
C9' | 0.0217 (18) | 0.0222 (16) | 0.0235 (19) | −0.0061 (13) | −0.0042 (15) | 0.0023 (13) |
C10' | 0.0197 (18) | 0.0232 (16) | 0.029 (2) | −0.0003 (14) | −0.0054 (16) | 0.0041 (14) |
C11' | 0.0259 (18) | 0.0218 (15) | 0.0121 (17) | 0.0031 (14) | −0.0042 (15) | 0.0016 (13) |
C12' | 0.0233 (17) | 0.0121 (14) | 0.0164 (18) | −0.0010 (13) | −0.0005 (14) | 0.0056 (12) |
C13' | 0.0226 (17) | 0.0159 (15) | 0.0167 (17) | −0.0022 (13) | −0.0034 (15) | −0.0002 (13) |
C14' | 0.0229 (17) | 0.0144 (14) | 0.0184 (18) | 0.0010 (12) | −0.0025 (15) | 0.0017 (12) |
C15' | 0.0264 (18) | 0.0241 (16) | 0.0195 (18) | −0.0013 (14) | 0.0030 (16) | 0.0018 (13) |
C16' | 0.040 (2) | 0.0250 (17) | 0.0194 (19) | 0.0009 (16) | −0.0024 (17) | −0.0002 (14) |
N17' | 0.0327 (16) | 0.0257 (14) | 0.0214 (16) | −0.0090 (12) | −0.0105 (14) | 0.0003 (11) |
C17' | 0.050 (3) | 0.038 (2) | 0.036 (2) | −0.0157 (19) | −0.017 (2) | −0.0013 (17) |
C8' | 0.036 (2) | 0.0160 (15) | 0.0220 (19) | −0.0033 (15) | −0.0030 (17) | 0.0004 (13) |
C7' | 0.0332 (19) | 0.0167 (14) | 0.0255 (19) | 0.0070 (14) | 0.0031 (17) | −0.0005 (13) |
Cl7' | 0.0429 (5) | 0.0234 (4) | 0.0401 (6) | 0.0115 (4) | −0.0003 (5) | −0.0041 (4) |
C1—C2 | 1.403 (4) | C1'—C2' | 1.377 (4) |
C1—C11 | 1.409 (4) | C1'—C11' | 1.403 (4) |
C1—H1A | 0.9500 | C1'—H1'A | 0.9500 |
C2—C3 | 1.402 (4) | C2'—C3' | 1.403 (4) |
C2—H2A | 0.9500 | C2'—H2'A | 0.9500 |
C3—O3 | 1.376 (4) | C3'—O3' | 1.376 (4) |
C3—C4 | 1.396 (4) | C3'—C4' | 1.390 (4) |
O3—C3A | 1.440 (4) | O3'—C3A' | 1.360 (5) |
C3A—H3AA | 0.9800 | C3A'—H3AD | 0.9800 |
C3A—H3AB | 0.9800 | C3A'—H3AE | 0.9800 |
C3A—H3AC | 0.9800 | C3A'—H3AF | 0.9800 |
C4—C12 | 1.386 (4) | C4'—O5' | 1.380 (4) |
C4—O5 | 1.382 (3) | C4'—C12' | 1.382 (4) |
O5—C5 | 1.480 (3) | O5'—C5' | 1.478 (3) |
C5—C13 | 1.530 (4) | C5'—C6' | 1.549 (4) |
C5—C6 | 1.547 (4) | C5'—C13' | 1.549 (4) |
C5—H5A | 1.0000 | C5'—H5'A | 1.0000 |
C6—O6 | 1.419 (3) | C6'—O6' | 1.424 (4) |
C6—C19 | 1.523 (4) | C6'—C19' | 1.511 (4) |
C6—C7 | 1.570 (4) | C6'—C7' | 1.560 (4) |
O6—C6A | 1.426 (4) | O6'—C6A' | 1.436 (4) |
C6A—H6AA | 0.9800 | C6A'—H6AD | 0.9800 |
C6A—H6AB | 0.9800 | C6A'—H6AE | 0.9800 |
C6A—H6AC | 0.9800 | C6A'—H6AF | 0.9800 |
C19—C18 | 1.325 (4) | C19'—C18' | 1.318 (4) |
C19—H19A | 0.9500 | C19'—H19C | 0.9500 |
C18—C14 | 1.522 (4) | C18'—C14' | 1.526 (4) |
C18—H18A | 0.9500 | C18'—H18B | 0.9500 |
C9—N17 | 1.479 (4) | C9'—N17' | 1.482 (4) |
C9—C14 | 1.548 (4) | C9'—C14' | 1.548 (4) |
C9—C10 | 1.569 (4) | C9'—C10' | 1.579 (4) |
C9—H9A | 1.0000 | C9'—H9'A | 1.0000 |
C10—C11 | 1.533 (4) | C10'—C11' | 1.514 (4) |
C10—H10A | 0.9900 | C10'—H10C | 0.9900 |
C10—H10B | 0.9900 | C10'—H10D | 0.9900 |
C11—C12 | 1.377 (4) | C11'—C12' | 1.384 (4) |
C12—C13 | 1.503 (4) | C12'—C13' | 1.499 (4) |
C13—C15 | 1.539 (4) | C13'—C14' | 1.548 (4) |
C13—C14 | 1.554 (4) | C13'—C15' | 1.557 (4) |
C14—C8 | 1.555 (4) | C14'—C8' | 1.548 (4) |
C15—C16 | 1.510 (4) | C15'—C16' | 1.521 (4) |
C15—H15A | 0.9900 | C15'—H15C | 0.9900 |
C15—H15B | 0.9900 | C15'—H15D | 0.9900 |
C16—N17 | 1.473 (4) | C16'—N17' | 1.476 (4) |
C16—H16A | 0.9900 | C16'—H16C | 0.9900 |
C16—H16B | 0.9900 | C16'—H16D | 0.9900 |
N17—C17A | 1.469 (4) | N17'—C17' | 1.477 (4) |
C17A—H17A | 0.9800 | C17'—H17D | 0.9800 |
C17A—H17B | 0.9800 | C17'—H17E | 0.9800 |
C17A—H17C | 0.9800 | C17'—H17F | 0.9800 |
C8—C7 | 1.559 (4) | C8'—C7' | 1.546 (4) |
C8—H8A | 0.9900 | C8'—H8'A | 0.9900 |
C8—H8B | 0.9900 | C8'—H8'B | 0.9900 |
C7—Cl7 | 1.809 (3) | C7'—Cl7' | 1.835 (3) |
C7—H7A | 1.0000 | C7'—H7'A | 1.0000 |
C2—C1—C11 | 120.9 (3) | C2'—C1'—C11' | 121.0 (3) |
C2—C1—H1A | 119.5 | C2'—C1'—H1'A | 119.5 |
C11—C1—H1A | 119.5 | C11'—C1'—H1'A | 119.5 |
C3—C2—C1 | 121.3 (3) | C1'—C2'—C3' | 122.1 (3) |
C3—C2—H2A | 119.3 | C1'—C2'—H2'A | 119.0 |
C1—C2—H2A | 119.3 | C3'—C2'—H2'A | 119.0 |
O3—C3—C4 | 117.6 (3) | O3'—C3'—C4' | 123.3 (3) |
O3—C3—C2 | 125.5 (3) | O3'—C3'—C2' | 119.7 (3) |
C4—C3—C2 | 116.9 (3) | C4'—C3'—C2' | 116.9 (3) |
C3—O3—C3A | 116.9 (2) | C3A'—O3'—C3' | 115.8 (3) |
O3—C3A—H3AA | 109.5 | O3'—C3A'—H3AD | 109.5 |
O3—C3A—H3AB | 109.5 | O3'—C3A'—H3AE | 109.5 |
H3AA—C3A—H3AB | 109.5 | H3AD—C3A'—H3AE | 109.5 |
O3—C3A—H3AC | 109.5 | O3'—C3A'—H3AF | 109.5 |
H3AA—C3A—H3AC | 109.5 | H3AD—C3A'—H3AF | 109.5 |
H3AB—C3A—H3AC | 109.5 | H3AE—C3A'—H3AF | 109.5 |
C12—C4—O5 | 113.2 (2) | O5'—C4'—C12' | 113.3 (2) |
C12—C4—C3 | 120.8 (3) | O5'—C4'—C3' | 126.4 (3) |
O5—C4—C3 | 125.5 (3) | C12'—C4'—C3' | 119.9 (3) |
C4—O5—C5 | 106.7 (2) | C4'—O5'—C5' | 107.0 (2) |
O5—C5—C13 | 107.5 (2) | O5'—C5'—C6' | 112.9 (2) |
O5—C5—C6 | 110.4 (2) | O5'—C5'—C13' | 106.8 (2) |
C13—C5—C6 | 109.2 (2) | C6'—C5'—C13' | 108.4 (2) |
O5—C5—H5A | 109.9 | O5'—C5'—H5'A | 109.5 |
C13—C5—H5A | 109.9 | C6'—C5'—H5'A | 109.5 |
C6—C5—H5A | 109.9 | C13'—C5'—H5'A | 109.5 |
O6—C6—C19 | 116.4 (2) | O6'—C6'—C19' | 115.4 (3) |
O6—C6—C5 | 105.3 (2) | O6'—C6'—C5' | 115.6 (3) |
C19—C6—C5 | 108.6 (2) | C19'—C6'—C5' | 108.9 (2) |
O6—C6—C7 | 114.4 (2) | O6'—C6'—C7' | 104.6 (2) |
C19—C6—C7 | 102.8 (2) | C19'—C6'—C7' | 103.9 (2) |
C5—C6—C7 | 109.2 (2) | C5'—C6'—C7' | 107.4 (3) |
C6—O6—C6A | 116.3 (2) | C6'—O6'—C6A' | 117.4 (2) |
O6—C6A—H6AA | 109.5 | O6'—C6A'—H6AD | 109.5 |
O6—C6A—H6AB | 109.5 | O6'—C6A'—H6AE | 109.5 |
H6AA—C6A—H6AB | 109.5 | H6AD—C6A'—H6AE | 109.5 |
O6—C6A—H6AC | 109.5 | O6'—C6A'—H6AF | 109.5 |
H6AA—C6A—H6AC | 109.5 | H6AD—C6A'—H6AF | 109.5 |
H6AB—C6A—H6AC | 109.5 | H6AE—C6A'—H6AF | 109.5 |
C18—C19—C6 | 115.0 (3) | C18'—C19'—C6' | 115.8 (3) |
C18—C19—H19A | 122.5 | C18'—C19'—H19C | 122.1 |
C6—C19—H19A | 122.5 | C6'—C19'—H19C | 122.1 |
C19—C18—C14 | 115.5 (3) | C19'—C18'—C14' | 115.0 (3) |
C19—C18—H18A | 122.3 | C19'—C18'—H18B | 122.5 |
C14—C18—H18A | 122.3 | C14'—C18'—H18B | 122.5 |
N17—C9—C14 | 107.9 (2) | N17'—C9'—C14' | 107.8 (3) |
N17—C9—C10 | 114.2 (2) | N17'—C9'—C10' | 115.2 (3) |
C14—C9—C10 | 111.9 (2) | C14'—C9'—C10' | 111.1 (2) |
N17—C9—H9A | 107.5 | N17'—C9'—H9'A | 107.5 |
C14—C9—H9A | 107.5 | C14'—C9'—H9'A | 107.5 |
C10—C9—H9A | 107.5 | C10'—C9'—H9'A | 107.5 |
C11—C10—C9 | 114.5 (2) | C11'—C10'—C9' | 115.0 (2) |
C11—C10—H10A | 108.6 | C11'—C10'—H10C | 108.5 |
C9—C10—H10A | 108.6 | C9'—C10'—H10C | 108.5 |
C11—C10—H10B | 108.6 | C11'—C10'—H10D | 108.5 |
C9—C10—H10B | 108.6 | C9'—C10'—H10D | 108.5 |
H10A—C10—H10B | 107.6 | H10C—C10'—H10D | 107.5 |
C12—C11—C1 | 116.2 (3) | C12'—C11'—C1' | 115.9 (3) |
C12—C11—C10 | 118.5 (3) | C12'—C11'—C10' | 118.6 (3) |
C1—C11—C10 | 124.1 (3) | C1'—C11'—C10' | 124.6 (3) |
C11—C12—C4 | 123.1 (3) | C4'—C12'—C11' | 123.3 (3) |
C11—C12—C13 | 125.7 (3) | C4'—C12'—C13' | 109.4 (3) |
C4—C12—C13 | 109.2 (2) | C11'—C12'—C13' | 125.4 (3) |
C12—C13—C5 | 102.2 (2) | C12'—C13'—C5' | 102.0 (2) |
C12—C13—C15 | 113.9 (2) | C12'—C13'—C14' | 104.6 (2) |
C5—C13—C15 | 112.1 (2) | C5'—C13'—C14' | 112.0 (2) |
C12—C13—C14 | 104.1 (2) | C12'—C13'—C15' | 113.5 (2) |
C5—C13—C14 | 112.2 (2) | C5'—C13'—C15' | 112.5 (3) |
C15—C13—C14 | 111.8 (2) | C14'—C13'—C15' | 111.7 (2) |
C18—C14—C9 | 114.7 (3) | C18'—C14'—C9' | 114.6 (3) |
C18—C14—C13 | 107.0 (2) | C18'—C14'—C8' | 105.2 (2) |
C9—C14—C13 | 106.0 (2) | C9'—C14'—C8' | 114.7 (2) |
C18—C14—C8 | 105.7 (2) | C18'—C14'—C13' | 107.1 (2) |
C9—C14—C8 | 115.1 (2) | C9'—C14'—C13' | 106.0 (2) |
C13—C14—C8 | 107.9 (2) | C8'—C14'—C13' | 108.9 (2) |
C16—C15—C13 | 112.7 (3) | C16'—C15'—C13' | 112.3 (3) |
C16—C15—H15A | 109.0 | C16'—C15'—H15C | 109.2 |
C13—C15—H15A | 109.0 | C13'—C15'—H15C | 109.2 |
C16—C15—H15B | 109.0 | C16'—C15'—H15D | 109.2 |
C13—C15—H15B | 109.0 | C13'—C15'—H15D | 109.2 |
H15A—C15—H15B | 107.8 | H15C—C15'—H15D | 107.9 |
N17—C16—C15 | 110.4 (2) | N17'—C16'—C15' | 109.5 (3) |
N17—C16—H16A | 109.6 | N17'—C16'—H16C | 109.8 |
C15—C16—H16A | 109.6 | C15'—C16'—H16C | 109.8 |
N17—C16—H16B | 109.6 | N17'—C16'—H16D | 109.8 |
C15—C16—H16B | 109.6 | C15'—C16'—H16D | 109.8 |
H16A—C16—H16B | 108.1 | H16C—C16'—H16D | 108.2 |
C17A—N17—C16 | 110.8 (2) | C17'—N17'—C16' | 110.7 (3) |
C17A—N17—C9 | 113.2 (2) | C17'—N17'—C9' | 112.8 (3) |
C16—N17—C9 | 112.3 (2) | C16'—N17'—C9' | 111.9 (2) |
N17—C17A—H17A | 109.5 | N17'—C17'—H17D | 109.5 |
N17—C17A—H17B | 109.5 | N17'—C17'—H17E | 109.5 |
H17A—C17A—H17B | 109.5 | H17D—C17'—H17E | 109.5 |
N17—C17A—H17C | 109.5 | N17'—C17'—H17F | 109.5 |
H17A—C17A—H17C | 109.5 | H17D—C17'—H17F | 109.5 |
H17B—C17A—H17C | 109.5 | H17E—C17'—H17F | 109.5 |
C14—C8—C7 | 108.4 (2) | C14'—C8'—C7' | 107.9 (2) |
C14—C8—H8A | 110.0 | C14'—C8'—H8'A | 110.1 |
C7—C8—H8A | 110.0 | C7'—C8'—H8'A | 110.1 |
C14—C8—H8B | 110.0 | C14'—C8'—H8'B | 110.1 |
C7—C8—H8B | 110.0 | C7'—C8'—H8'B | 110.1 |
H8A—C8—H8B | 108.4 | H8'A—C8'—H8'B | 108.4 |
C8—C7—C6 | 111.3 (2) | C8'—C7'—C6' | 112.5 (2) |
C8—C7—Cl7 | 111.2 (2) | C8'—C7'—Cl7' | 110.7 (2) |
C6—C7—Cl7 | 112.0 (2) | C6'—C7'—Cl7' | 110.6 (2) |
C8—C7—H7A | 107.4 | C8'—C7'—H7'A | 107.6 |
C6—C7—H7A | 107.4 | C6'—C7'—H7'A | 107.6 |
Cl7—C7—H7A | 107.4 | Cl7'—C7'—H7'A | 107.6 |
C11—C1—C2—C3 | −3.3 (5) | C11'—C1'—C2'—C3' | −4.1 (5) |
C1—C2—C3—O3 | −173.7 (3) | C1'—C2'—C3'—O3' | −178.1 (3) |
C1—C2—C3—C4 | 4.5 (5) | C1'—C2'—C3'—C4' | 3.7 (5) |
C4—C3—O3—C3A | −165.8 (3) | C4'—C3'—O3'—C3A' | −69.6 (5) |
C2—C3—O3—C3A | 12.4 (5) | C2'—C3'—O3'—C3A' | 112.2 (4) |
O3—C3—C4—C12 | 179.5 (3) | O3'—C3'—C4'—O5' | 12.6 (5) |
C2—C3—C4—C12 | 1.2 (5) | C2'—C3'—C4'—O5' | −169.2 (3) |
O3—C3—C4—O5 | 8.5 (5) | O3'—C3'—C4'—C12' | −174.8 (3) |
C2—C3—C4—O5 | −169.9 (3) | C2'—C3'—C4'—C12' | 3.3 (5) |
C12—C4—O5—C5 | −5.7 (3) | C12'—C4'—O5'—C5' | −5.8 (3) |
C3—C4—O5—C5 | 165.9 (3) | C3'—C4'—O5'—C5' | 167.2 (3) |
C4—O5—C5—C13 | 10.2 (3) | C4'—O5'—C5'—C6' | −108.0 (3) |
C4—O5—C5—C6 | −108.8 (3) | C4'—O5'—C5'—C13' | 11.1 (3) |
O5—C5—C6—O6 | −59.8 (3) | O5'—C5'—C6'—O6' | −66.3 (3) |
C13—C5—C6—O6 | −177.9 (2) | C13'—C5'—C6'—O6' | 175.5 (2) |
O5—C5—C6—C19 | 65.5 (3) | O5'—C5'—C6'—C19' | 65.5 (3) |
C13—C5—C6—C19 | −52.5 (3) | C13'—C5'—C6'—C19' | −52.7 (3) |
O5—C5—C6—C7 | 176.9 (2) | O5'—C5'—C6'—C7' | 177.4 (2) |
C13—C5—C6—C7 | 58.9 (3) | C13'—C5'—C6'—C7' | 59.2 (3) |
C19—C6—O6—C6A | 62.7 (3) | C19'—C6'—O6'—C6A' | −58.5 (4) |
C5—C6—O6—C6A | −176.9 (3) | C5'—C6'—O6'—C6A' | 70.2 (4) |
C7—C6—O6—C6A | −57.0 (3) | C7'—C6'—O6'—C6A' | −172.0 (3) |
O6—C6—C19—C18 | 175.8 (3) | O6'—C6'—C19'—C18' | −171.1 (2) |
C5—C6—C19—C18 | 57.3 (3) | C5'—C6'—C19'—C18' | 57.0 (3) |
C7—C6—C19—C18 | −58.4 (3) | C7'—C6'—C19'—C18' | −57.2 (3) |
C6—C19—C18—C14 | −1.1 (4) | C6'—C19'—C18'—C14' | −0.1 (4) |
N17—C9—C10—C11 | −97.1 (3) | N17'—C9'—C10'—C11' | −96.4 (3) |
C14—C9—C10—C11 | 25.8 (4) | C14'—C9'—C10'—C11' | 26.4 (4) |
C2—C1—C11—C12 | −3.7 (4) | C2'—C1'—C11'—C12' | −2.6 (5) |
C2—C1—C11—C10 | 164.0 (3) | C2'—C1'—C11'—C10' | 166.5 (3) |
C9—C10—C11—C12 | 5.0 (4) | C9'—C10'—C11'—C12' | 4.5 (4) |
C9—C10—C11—C1 | −162.4 (3) | C9'—C10'—C11'—C1' | −164.4 (3) |
C1—C11—C12—C4 | 9.7 (5) | O5'—C4'—C12'—C11' | 162.9 (3) |
C10—C11—C12—C4 | −158.7 (3) | C3'—C4'—C12'—C11' | −10.6 (5) |
C1—C11—C12—C13 | 171.7 (3) | O5'—C4'—C12'—C13' | −2.2 (4) |
C10—C11—C12—C13 | 3.4 (5) | C3'—C4'—C12'—C13' | −175.7 (3) |
O5—C4—C12—C11 | 163.4 (3) | C1'—C11'—C12'—C4' | 10.0 (5) |
C3—C4—C12—C11 | −8.7 (5) | C10'—C11'—C12'—C4' | −159.8 (3) |
O5—C4—C12—C13 | −1.2 (4) | C1'—C11'—C12'—C13' | 172.7 (3) |
C3—C4—C12—C13 | −173.3 (3) | C10'—C11'—C12'—C13' | 2.9 (5) |
C11—C12—C13—C5 | −156.9 (3) | C4'—C12'—C13'—C5' | 8.7 (3) |
C4—C12—C13—C5 | 7.3 (3) | C11'—C12'—C13'—C5' | −156.0 (3) |
C11—C12—C13—C15 | 82.0 (4) | C4'—C12'—C13'—C14' | 125.5 (3) |
C4—C12—C13—C15 | −113.8 (3) | C11'—C12'—C13'—C14' | −39.2 (4) |
C11—C12—C13—C14 | −40.0 (4) | C4'—C12'—C13'—C15' | −112.5 (3) |
C4—C12—C13—C14 | 124.2 (3) | C11'—C12'—C13'—C15' | 82.8 (4) |
O5—C5—C13—C12 | −10.5 (3) | O5'—C5'—C13'—C12' | −11.8 (3) |
C6—C5—C13—C12 | 109.3 (3) | C6'—C5'—C13'—C12' | 110.2 (3) |
O5—C5—C13—C15 | 111.9 (3) | O5'—C5'—C13'—C14' | −123.1 (3) |
C6—C5—C13—C15 | −128.3 (2) | C6'—C5'—C13'—C14' | −1.1 (3) |
O5—C5—C13—C14 | −121.4 (2) | O5'—C5'—C13'—C15' | 110.0 (3) |
C6—C5—C13—C14 | −1.6 (3) | C6'—C5'—C13'—C15' | −128.0 (3) |
C19—C18—C14—C9 | −171.6 (3) | C19'—C18'—C14'—C9' | −172.7 (2) |
C19—C18—C14—C13 | −54.4 (3) | C19'—C18'—C14'—C8' | 60.4 (3) |
C19—C18—C14—C8 | 60.5 (3) | C19'—C18'—C14'—C13' | −55.4 (3) |
N17—C9—C14—C18 | −178.8 (2) | N17'—C9'—C14'—C18' | −178.2 (2) |
C10—C9—C14—C18 | 54.7 (3) | C10'—C9'—C14'—C18' | 54.7 (3) |
N17—C9—C14—C13 | 63.3 (3) | N17'—C9'—C14'—C8' | −56.4 (3) |
C10—C9—C14—C13 | −63.1 (3) | C10'—C9'—C14'—C8' | 176.6 (3) |
N17—C9—C14—C8 | −55.9 (3) | N17'—C9'—C14'—C13' | 63.8 (3) |
C10—C9—C14—C8 | 177.7 (2) | C10'—C9'—C14'—C13' | −63.2 (3) |
C12—C13—C14—C18 | −55.9 (3) | C12'—C13'—C14'—C18' | −56.0 (3) |
C5—C13—C14—C18 | 53.8 (3) | C5'—C13'—C14'—C18' | 53.6 (3) |
C15—C13—C14—C18 | −179.3 (2) | C15'—C13'—C14'—C18' | −179.1 (2) |
C12—C13—C14—C9 | 66.9 (3) | C12'—C13'—C14'—C9' | 66.8 (3) |
C5—C13—C14—C9 | 176.6 (2) | C5'—C13'—C14'—C9' | 176.5 (2) |
C15—C13—C14—C9 | −56.5 (3) | C15'—C13'—C14'—C9' | −56.3 (3) |
C12—C13—C14—C8 | −169.3 (2) | C12'—C13'—C14'—C8' | −169.3 (2) |
C5—C13—C14—C8 | −59.5 (3) | C5'—C13'—C14'—C8' | −59.6 (3) |
C15—C13—C14—C8 | 67.3 (3) | C15'—C13'—C14'—C8' | 67.6 (3) |
C12—C13—C15—C16 | −66.7 (3) | C12'—C13'—C15'—C16' | −66.8 (3) |
C5—C13—C15—C16 | 177.9 (2) | C5'—C13'—C15'—C16' | 178.2 (2) |
C14—C13—C15—C16 | 51.0 (3) | C14'—C13'—C15'—C16' | 51.2 (3) |
C13—C15—C16—N17 | −49.6 (3) | C13'—C15'—C16'—N17' | −50.6 (3) |
C15—C16—N17—C17A | −173.6 (2) | C15'—C16'—N17'—C17' | −172.9 (3) |
C15—C16—N17—C9 | 58.7 (3) | C15'—C16'—N17'—C9' | 60.4 (3) |
C14—C9—N17—C17A | 166.6 (2) | C14'—C9'—N17'—C17' | 166.0 (2) |
C10—C9—N17—C17A | −68.4 (3) | C10'—C9'—N17'—C17' | −69.4 (3) |
C14—C9—N17—C16 | −67.0 (3) | C14'—C9'—N17'—C16' | −68.5 (3) |
C10—C9—N17—C16 | 58.0 (3) | C10'—C9'—N17'—C16' | 56.2 (3) |
C18—C14—C8—C7 | −52.8 (3) | C18'—C14'—C8'—C7' | −56.4 (3) |
C9—C14—C8—C7 | 179.5 (2) | C9'—C14'—C8'—C7' | 176.7 (2) |
C13—C14—C8—C7 | 61.4 (3) | C13'—C14'—C8'—C7' | 58.1 (3) |
C14—C8—C7—C6 | −4.7 (3) | C14'—C8'—C7'—C6' | 1.0 (4) |
C14—C8—C7—Cl7 | −130.3 (2) | C14'—C8'—C7'—Cl7' | −123.4 (2) |
O6—C6—C7—C8 | −173.7 (2) | O6'—C6'—C7'—C8' | 175.9 (3) |
C19—C6—C7—C8 | 59.1 (3) | C19'—C6'—C7'—C8' | 54.4 (3) |
C5—C6—C7—C8 | −56.1 (3) | C5'—C6'—C7'—C8' | −60.8 (3) |
O6—C6—C7—Cl7 | −48.6 (3) | O6'—C6'—C7'—Cl7' | −59.7 (3) |
C19—C6—C7—Cl7 | −175.7 (2) | C19'—C6'—C7'—Cl7' | 178.9 (2) |
C5—C6—C7—Cl7 | 69.1 (3) | C5'—C6'—C7'—Cl7' | 63.6 (3) |