Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107033690/hj3044sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270107033690/hj3044Isup2.hkl |
CCDC reference: 659146
The title compound was prepared according to the previously reported procedure of Sonar et al. (2004). Crystallization from ethyl acetate afforded yellow crystals [colourless given in experimental tables - which is correct?]. 1H NMR (CDCl3, δ, p.p.m.): 1.47–1.89 (m, 5H), 2.05 (s, 1H), 2.74–3.00 (m, 4H), 4.34 (s, 1H), 6.59 (s, 1H), 6.97 (d, 2H), 7.25 (d, 1H); 13C NMR (CDCl3, δ, p.p.m.): 19.07, 25.37, 31.09, 46.64, 47.77, 70.61, 116.83, 125.47, 126.95, 127.49, 138.53, 149.20.
H atoms were found in a difference Fourier map and subsequently placed in idealized positions with constrained C—H distances of 0.95 Å (Csp2—H), 0.99 Å (CH2) and 1.00 Å (CH) and with O—H = 0.84 Å. Uiso(H) values were set to either 1.2Ueq or 1.5eq (OH only) of the parent atom.
Data collection: COLLECT (Nonius, 1999); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1995); software used to prepare material for publication: SHELX97 and local procedures.
C12H15NOS | F(000) = 1888 |
Mr = 221.32 | Dx = 1.338 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 19446 reflections |
a = 14.7933 (3) Å | θ = 1.0–27.5° |
b = 20.0349 (4) Å | µ = 0.27 mm−1 |
c = 14.8243 (3) Å | T = 90 K |
β = 90.2820 (7)° | Thin plate, colourless |
V = 4393.61 (15) Å3 | 0.38 × 0.35 × 0.03 mm |
Z = 16 |
Nonius KappaCCD area-detector diffractometer | 10043 independent reflections |
Radiation source: fine-focus sealed tube | 7113 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
Detector resolution: 18 pixels mm-1 | θmax = 27.5°, θmin = 1.7° |
ω scans at fixed χ = 55° | h = −19→19 |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | k = −25→25 |
Tmin = 0.906, Tmax = 0.992 | l = −19→19 |
37339 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0549P)2 + 1.4384P] where P = (Fo2 + 2Fc2)/3 |
10043 reflections | (Δ/σ)max = 0.001 |
545 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
C12H15NOS | V = 4393.61 (15) Å3 |
Mr = 221.32 | Z = 16 |
Monoclinic, P21/n | Mo Kα radiation |
a = 14.7933 (3) Å | µ = 0.27 mm−1 |
b = 20.0349 (4) Å | T = 90 K |
c = 14.8243 (3) Å | 0.38 × 0.35 × 0.03 mm |
β = 90.2820 (7)° |
Nonius KappaCCD area-detector diffractometer | 10043 independent reflections |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | 7113 reflections with I > 2σ(I) |
Tmin = 0.906, Tmax = 0.992 | Rint = 0.058 |
37339 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.31 e Å−3 |
10043 reflections | Δρmin = −0.34 e Å−3 |
545 parameters |
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 > 2σ(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 | ||
S1A | 0.74404 (3) | 0.14937 (2) | 0.53118 (3) | 0.02089 (12) | |
N1A | 0.73352 (11) | 0.29039 (8) | 0.55614 (10) | 0.0198 (3) | |
O1A | 0.63637 (9) | 0.38409 (7) | 0.37043 (8) | 0.0211 (3) | |
H1A | 0.6859 | 0.3752 | 0.3457 | 0.032* | |
C1A | 0.66001 (12) | 0.17545 (9) | 0.45713 (12) | 0.0179 (4) | |
C2A | 0.72215 (14) | 0.06691 (9) | 0.50794 (13) | 0.0252 (4) | |
H2A | 0.7545 | 0.0307 | 0.5340 | 0.030* | |
C3A | 0.65327 (14) | 0.05956 (10) | 0.44797 (13) | 0.0271 (5) | |
H3A | 0.6313 | 0.0175 | 0.4281 | 0.033* | |
C4A | 0.61785 (13) | 0.12123 (9) | 0.41829 (13) | 0.0229 (4) | |
H4A | 0.5698 | 0.1250 | 0.3758 | 0.027* | |
C5A | 0.63713 (13) | 0.24501 (9) | 0.43981 (12) | 0.0181 (4) | |
H5A | 0.5959 | 0.2534 | 0.3918 | 0.022* | |
C6A | 0.66827 (12) | 0.29805 (9) | 0.48452 (12) | 0.0169 (4) | |
C7A | 0.81976 (13) | 0.31909 (9) | 0.52400 (13) | 0.0216 (4) | |
H7A1 | 0.8425 | 0.2922 | 0.4728 | 0.026* | |
H7A2 | 0.8653 | 0.3170 | 0.5731 | 0.026* | |
C8A | 0.80757 (13) | 0.39255 (9) | 0.49348 (12) | 0.0196 (4) | |
H8A1 | 0.8514 | 0.4215 | 0.5255 | 0.024* | |
H8A2 | 0.8186 | 0.3964 | 0.4279 | 0.024* | |
C9A | 0.71054 (13) | 0.41447 (9) | 0.51522 (12) | 0.0195 (4) | |
H9A | 0.7014 | 0.4624 | 0.4987 | 0.023* | |
C10A | 0.64266 (13) | 0.37025 (9) | 0.46493 (12) | 0.0172 (4) | |
H10A | 0.5817 | 0.3784 | 0.4917 | 0.021* | |
C11A | 0.69522 (14) | 0.40421 (9) | 0.61635 (12) | 0.0224 (4) | |
H11A | 0.6346 | 0.4207 | 0.6334 | 0.027* | |
H11B | 0.7411 | 0.4292 | 0.6516 | 0.027* | |
C12A | 0.70305 (14) | 0.32849 (9) | 0.63614 (12) | 0.0232 (4) | |
H12A | 0.7465 | 0.3215 | 0.6863 | 0.028* | |
H12B | 0.6435 | 0.3114 | 0.6556 | 0.028* | |
S1B | 0.93186 (3) | 0.13285 (2) | 0.14966 (3) | 0.02178 (12) | |
N1B | 0.96319 (11) | 0.27513 (8) | 0.15764 (10) | 0.0193 (3) | |
O1B | 0.78363 (9) | 0.37379 (7) | 0.25620 (8) | 0.0226 (3) | |
H1B | 0.7609 | 0.3745 | 0.2042 | 0.034* | |
C1B | 0.86176 (13) | 0.16189 (9) | 0.23453 (12) | 0.0191 (4) | |
C2B | 0.90240 (14) | 0.05155 (10) | 0.17130 (14) | 0.0273 (5) | |
H2B | 0.9251 | 0.0145 | 0.1385 | 0.033* | |
C3B | 0.84319 (14) | 0.04622 (10) | 0.24033 (14) | 0.0295 (5) | |
H3B | 0.8202 | 0.0050 | 0.2619 | 0.035* | |
C4B | 0.81938 (14) | 0.10933 (10) | 0.27672 (13) | 0.0246 (4) | |
H4B | 0.7784 | 0.1148 | 0.3253 | 0.029* | |
C5B | 0.84853 (12) | 0.23191 (9) | 0.25679 (12) | 0.0182 (4) | |
H5B | 0.8027 | 0.2415 | 0.2996 | 0.022* | |
C6B | 0.89334 (12) | 0.28421 (9) | 0.22398 (11) | 0.0172 (4) | |
C7B | 0.93158 (13) | 0.30690 (9) | 0.07280 (12) | 0.0214 (4) | |
H7B1 | 0.8778 | 0.2828 | 0.0499 | 0.026* | |
H7B2 | 0.9796 | 0.3035 | 0.0268 | 0.026* | |
C8B | 0.90717 (13) | 0.38129 (9) | 0.08751 (12) | 0.0210 (4) | |
H8B1 | 0.9415 | 0.4096 | 0.0450 | 0.025* | |
H8B2 | 0.8418 | 0.3883 | 0.0763 | 0.025* | |
C9B | 0.93096 (13) | 0.40027 (9) | 0.18530 (12) | 0.0198 (4) | |
H9B | 0.9179 | 0.4485 | 0.1964 | 0.024* | |
C10B | 0.87748 (13) | 0.35634 (9) | 0.25050 (12) | 0.0184 (4) | |
H10B | 0.9044 | 0.3627 | 0.3119 | 0.022* | |
C11B | 1.03170 (12) | 0.38560 (9) | 0.19972 (13) | 0.0196 (4) | |
H11C | 1.0507 | 0.3999 | 0.2609 | 0.024* | |
H11D | 1.0682 | 0.4103 | 0.1549 | 0.024* | |
C12B | 1.04625 (13) | 0.30969 (9) | 0.18858 (13) | 0.0212 (4) | |
H12C | 1.0951 | 0.3019 | 0.1444 | 0.025* | |
H12D | 1.0658 | 0.2905 | 0.2471 | 0.025* | |
S1C | 0.55607 (3) | 0.15589 (2) | −0.04202 (3) | 0.02126 (12) | |
N1C | 0.56311 (10) | 0.29615 (8) | −0.06757 (10) | 0.0192 (3) | |
O1C | 0.66761 (9) | 0.39559 (7) | 0.10825 (8) | 0.0218 (3) | |
H1C | 0.6170 | 0.3922 | 0.1333 | 0.033* | |
C1C | 0.63776 (12) | 0.18331 (9) | 0.03381 (12) | 0.0192 (4) | |
C2C | 0.57733 (14) | 0.07408 (10) | −0.01553 (13) | 0.0263 (5) | |
H2C | 0.5465 | 0.0374 | −0.0423 | 0.032* | |
C3C | 0.64337 (14) | 0.06755 (10) | 0.04811 (13) | 0.0265 (5) | |
H3C | 0.6640 | 0.0259 | 0.0707 | 0.032* | |
C4C | 0.67774 (13) | 0.13009 (10) | 0.07684 (13) | 0.0238 (4) | |
H4C | 0.7238 | 0.1348 | 0.1213 | 0.029* | |
C5C | 0.66225 (13) | 0.25306 (9) | 0.04761 (12) | 0.0193 (4) | |
H5C | 0.7048 | 0.2622 | 0.0942 | 0.023* | |
C6C | 0.63075 (12) | 0.30530 (9) | 0.00118 (12) | 0.0181 (4) | |
C7C | 0.47919 (13) | 0.32917 (9) | −0.03644 (13) | 0.0221 (4) | |
H7C1 | 0.4567 | 0.3061 | 0.0180 | 0.027* | |
H7C2 | 0.4322 | 0.3255 | −0.0840 | 0.027* | |
C8C | 0.49557 (13) | 0.40369 (9) | −0.01431 (13) | 0.0213 (4) | |
H8C1 | 0.4532 | 0.4319 | −0.0494 | 0.026* | |
H8C2 | 0.4852 | 0.4119 | 0.0507 | 0.026* | |
C9C | 0.59352 (13) | 0.42112 (9) | −0.03875 (12) | 0.0203 (4) | |
H9C | 0.6057 | 0.4694 | −0.0268 | 0.024* | |
C10C | 0.65939 (13) | 0.37735 (9) | 0.01526 (12) | 0.0191 (4) | |
H10C | 0.7204 | 0.3827 | −0.0125 | 0.023* | |
C11C | 0.60677 (14) | 0.40524 (9) | −0.13907 (12) | 0.0224 (4) | |
H11E | 0.6682 | 0.4186 | −0.1583 | 0.027* | |
H11F | 0.5620 | 0.4299 | −0.1761 | 0.027* | |
C12C | 0.59377 (14) | 0.32888 (9) | −0.15126 (12) | 0.0217 (4) | |
H12E | 0.5488 | 0.3208 | −0.1997 | 0.026* | |
H12F | 0.6517 | 0.3087 | −0.1703 | 0.026* | |
S1D | 0.36722 (3) | 0.15446 (2) | 0.34283 (3) | 0.02194 (12) | |
N1D | 0.34369 (11) | 0.29662 (8) | 0.33218 (10) | 0.0214 (4) | |
O1D | 0.51971 (9) | 0.39123 (7) | 0.22320 (8) | 0.0220 (3) | |
H1D | 0.5448 | 0.3871 | 0.2739 | 0.033* | |
C1D | 0.43724 (13) | 0.18024 (9) | 0.25578 (12) | 0.0194 (4) | |
C2D | 0.38858 (14) | 0.07187 (10) | 0.32030 (13) | 0.0264 (5) | |
H2D | 0.3636 | 0.0359 | 0.3536 | 0.032* | |
C3D | 0.44544 (14) | 0.06396 (10) | 0.24928 (13) | 0.0258 (5) | |
H3D | 0.4642 | 0.0218 | 0.2268 | 0.031* | |
C4D | 0.47342 (14) | 0.12584 (10) | 0.21279 (13) | 0.0231 (4) | |
H4D | 0.5135 | 0.1294 | 0.1632 | 0.028* | |
C5D | 0.45272 (13) | 0.24932 (9) | 0.23074 (12) | 0.0184 (4) | |
H5D | 0.4979 | 0.2571 | 0.1866 | 0.022* | |
C6D | 0.41065 (12) | 0.30306 (9) | 0.26271 (12) | 0.0180 (4) | |
C7D | 0.37643 (14) | 0.33301 (9) | 0.41320 (12) | 0.0234 (4) | |
H7D1 | 0.4309 | 0.3104 | 0.4374 | 0.028* | |
H7D2 | 0.3293 | 0.3317 | 0.4603 | 0.028* | |
C8D | 0.39972 (13) | 0.40673 (9) | 0.39147 (12) | 0.0218 (4) | |
H8D1 | 0.3663 | 0.4369 | 0.4323 | 0.026* | |
H8D2 | 0.4653 | 0.4146 | 0.4000 | 0.026* | |
C9D | 0.37273 (13) | 0.42054 (9) | 0.29291 (12) | 0.0203 (4) | |
H9D | 0.3843 | 0.4683 | 0.2772 | 0.024* | |
C10D | 0.42616 (12) | 0.37421 (9) | 0.23040 (12) | 0.0181 (4) | |
H10D | 0.3989 | 0.3781 | 0.1687 | 0.022* | |
C11D | 0.27217 (13) | 0.40402 (10) | 0.28181 (13) | 0.0238 (4) | |
H11G | 0.2518 | 0.4151 | 0.2199 | 0.029* | |
H11H | 0.2360 | 0.4305 | 0.3249 | 0.029* | |
C12D | 0.25918 (13) | 0.32856 (10) | 0.30002 (14) | 0.0251 (4) | |
H12G | 0.2115 | 0.3225 | 0.3459 | 0.030* | |
H12H | 0.2388 | 0.3064 | 0.2438 | 0.030* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0192 (3) | 0.0217 (2) | 0.0218 (2) | 0.00158 (19) | −0.00060 (19) | 0.00124 (19) |
N1A | 0.0229 (9) | 0.0207 (8) | 0.0158 (8) | −0.0020 (7) | −0.0032 (7) | −0.0001 (6) |
O1A | 0.0189 (7) | 0.0276 (7) | 0.0167 (7) | 0.0021 (6) | 0.0016 (5) | 0.0027 (5) |
C1A | 0.0153 (10) | 0.0201 (9) | 0.0184 (9) | 0.0006 (8) | 0.0034 (7) | −0.0018 (7) |
C2A | 0.0263 (11) | 0.0194 (10) | 0.0300 (11) | 0.0023 (8) | 0.0079 (9) | 0.0025 (8) |
C3A | 0.0294 (12) | 0.0214 (10) | 0.0307 (11) | −0.0036 (9) | 0.0067 (9) | −0.0053 (8) |
C4A | 0.0205 (11) | 0.0248 (10) | 0.0233 (10) | −0.0016 (8) | −0.0002 (8) | −0.0045 (8) |
C5A | 0.0150 (10) | 0.0227 (10) | 0.0167 (9) | 0.0010 (8) | 0.0013 (7) | −0.0007 (7) |
C6A | 0.0143 (10) | 0.0220 (10) | 0.0144 (9) | 0.0008 (7) | 0.0018 (7) | 0.0012 (7) |
C7A | 0.0181 (10) | 0.0229 (10) | 0.0238 (10) | 0.0017 (8) | −0.0022 (8) | −0.0027 (8) |
C8A | 0.0189 (10) | 0.0224 (10) | 0.0176 (9) | −0.0030 (8) | 0.0026 (8) | −0.0004 (7) |
C9A | 0.0210 (10) | 0.0176 (9) | 0.0199 (10) | −0.0012 (8) | 0.0019 (8) | 0.0001 (7) |
C10A | 0.0176 (10) | 0.0193 (9) | 0.0148 (9) | 0.0009 (8) | 0.0019 (7) | 0.0024 (7) |
C11A | 0.0242 (11) | 0.0236 (10) | 0.0194 (10) | −0.0018 (8) | 0.0042 (8) | −0.0042 (8) |
C12A | 0.0295 (12) | 0.0265 (11) | 0.0135 (9) | −0.0049 (9) | 0.0009 (8) | −0.0010 (8) |
S1B | 0.0223 (3) | 0.0215 (2) | 0.0215 (3) | 0.0001 (2) | 0.0020 (2) | −0.00228 (19) |
N1B | 0.0188 (9) | 0.0203 (8) | 0.0189 (8) | −0.0002 (7) | 0.0030 (7) | 0.0005 (6) |
O1B | 0.0180 (7) | 0.0315 (8) | 0.0181 (7) | 0.0065 (6) | 0.0015 (5) | −0.0007 (6) |
C1B | 0.0181 (10) | 0.0247 (10) | 0.0144 (9) | −0.0003 (8) | −0.0012 (7) | 0.0002 (7) |
C2B | 0.0323 (12) | 0.0186 (10) | 0.0310 (11) | −0.0001 (9) | −0.0037 (9) | −0.0029 (8) |
C3B | 0.0339 (13) | 0.0230 (11) | 0.0314 (12) | −0.0063 (9) | −0.0008 (10) | 0.0038 (9) |
C4B | 0.0266 (11) | 0.0252 (10) | 0.0219 (10) | −0.0041 (9) | 0.0023 (8) | 0.0016 (8) |
C5B | 0.0170 (10) | 0.0234 (10) | 0.0141 (9) | 0.0006 (8) | 0.0014 (7) | −0.0001 (7) |
C6B | 0.0146 (10) | 0.0232 (10) | 0.0140 (9) | 0.0011 (7) | −0.0014 (7) | −0.0006 (7) |
C7B | 0.0234 (11) | 0.0246 (10) | 0.0163 (9) | −0.0039 (8) | 0.0028 (8) | −0.0014 (7) |
C8B | 0.0194 (10) | 0.0261 (11) | 0.0175 (10) | 0.0013 (8) | −0.0004 (8) | 0.0025 (8) |
C9B | 0.0213 (10) | 0.0186 (9) | 0.0195 (10) | 0.0010 (8) | 0.0001 (8) | −0.0001 (7) |
C10B | 0.0171 (10) | 0.0230 (10) | 0.0152 (9) | 0.0030 (8) | −0.0007 (7) | −0.0012 (7) |
C11B | 0.0180 (10) | 0.0204 (10) | 0.0204 (10) | −0.0017 (8) | −0.0020 (8) | 0.0013 (7) |
C12B | 0.0163 (10) | 0.0206 (10) | 0.0267 (10) | 0.0016 (8) | 0.0027 (8) | 0.0020 (8) |
S1C | 0.0210 (3) | 0.0235 (2) | 0.0194 (2) | −0.0027 (2) | 0.00001 (19) | −0.00086 (19) |
N1C | 0.0174 (9) | 0.0220 (8) | 0.0182 (8) | −0.0004 (7) | −0.0030 (6) | −0.0011 (6) |
O1C | 0.0186 (7) | 0.0299 (7) | 0.0169 (7) | −0.0016 (6) | 0.0008 (5) | −0.0055 (6) |
C1C | 0.0157 (10) | 0.0252 (10) | 0.0169 (9) | 0.0003 (8) | 0.0016 (7) | −0.0016 (7) |
C2C | 0.0281 (12) | 0.0232 (10) | 0.0277 (11) | −0.0033 (9) | 0.0078 (9) | −0.0039 (8) |
C3C | 0.0261 (12) | 0.0226 (11) | 0.0309 (11) | 0.0044 (9) | 0.0077 (9) | 0.0032 (8) |
C4C | 0.0202 (11) | 0.0275 (11) | 0.0238 (10) | 0.0031 (8) | 0.0010 (8) | 0.0027 (8) |
C5C | 0.0161 (10) | 0.0242 (10) | 0.0174 (9) | −0.0014 (8) | 0.0013 (7) | −0.0017 (7) |
C6C | 0.0155 (10) | 0.0241 (10) | 0.0147 (9) | −0.0003 (8) | 0.0021 (7) | −0.0010 (7) |
C7C | 0.0161 (10) | 0.0279 (11) | 0.0223 (10) | −0.0010 (8) | −0.0015 (8) | 0.0025 (8) |
C8C | 0.0193 (10) | 0.0267 (11) | 0.0178 (10) | 0.0034 (8) | 0.0019 (8) | 0.0005 (8) |
C9C | 0.0222 (11) | 0.0176 (9) | 0.0209 (10) | −0.0006 (8) | 0.0000 (8) | −0.0009 (7) |
C10C | 0.0182 (10) | 0.0233 (10) | 0.0159 (9) | −0.0016 (8) | 0.0018 (7) | −0.0034 (7) |
C11C | 0.0236 (11) | 0.0258 (11) | 0.0179 (10) | −0.0014 (8) | 0.0016 (8) | 0.0042 (8) |
C12C | 0.0236 (11) | 0.0265 (11) | 0.0151 (9) | 0.0028 (8) | 0.0005 (8) | −0.0019 (8) |
S1D | 0.0219 (3) | 0.0238 (3) | 0.0201 (3) | −0.0011 (2) | 0.0026 (2) | 0.00269 (19) |
N1D | 0.0214 (9) | 0.0239 (9) | 0.0190 (8) | −0.0009 (7) | 0.0056 (7) | −0.0016 (6) |
O1D | 0.0182 (7) | 0.0302 (8) | 0.0176 (7) | −0.0036 (6) | 0.0006 (5) | 0.0017 (6) |
C1D | 0.0172 (10) | 0.0249 (10) | 0.0161 (9) | 0.0000 (8) | −0.0017 (7) | 0.0009 (7) |
C2D | 0.0280 (12) | 0.0223 (10) | 0.0289 (11) | −0.0027 (9) | −0.0037 (9) | 0.0045 (8) |
C3D | 0.0311 (12) | 0.0216 (10) | 0.0247 (11) | 0.0041 (9) | −0.0048 (9) | −0.0008 (8) |
C4D | 0.0255 (11) | 0.0256 (10) | 0.0182 (10) | 0.0045 (9) | −0.0005 (8) | 0.0005 (8) |
C5D | 0.0160 (10) | 0.0241 (10) | 0.0152 (9) | −0.0004 (8) | 0.0018 (7) | 0.0015 (7) |
C6D | 0.0160 (10) | 0.0229 (10) | 0.0151 (9) | −0.0009 (8) | −0.0003 (7) | 0.0007 (7) |
C7D | 0.0268 (11) | 0.0277 (11) | 0.0156 (9) | 0.0032 (9) | 0.0030 (8) | −0.0003 (8) |
C8D | 0.0209 (11) | 0.0238 (10) | 0.0207 (10) | 0.0012 (8) | −0.0007 (8) | −0.0034 (8) |
C9D | 0.0207 (10) | 0.0185 (9) | 0.0216 (10) | 0.0010 (8) | 0.0004 (8) | 0.0012 (7) |
C10D | 0.0157 (10) | 0.0215 (10) | 0.0170 (9) | −0.0010 (8) | 0.0002 (8) | 0.0014 (7) |
C11D | 0.0181 (10) | 0.0301 (11) | 0.0231 (10) | 0.0047 (8) | −0.0017 (8) | −0.0007 (8) |
C12D | 0.0180 (11) | 0.0302 (11) | 0.0272 (11) | −0.0005 (8) | 0.0038 (8) | −0.0035 (8) |
S1A—C2A | 1.718 (2) | S1C—C2C | 1.714 (2) |
S1A—C1A | 1.7350 (19) | S1C—C1C | 1.7357 (19) |
N1A—C6A | 1.440 (2) | N1C—C6C | 1.436 (2) |
N1A—C7A | 1.480 (2) | N1C—C12C | 1.477 (2) |
N1A—C12A | 1.482 (2) | N1C—C7C | 1.482 (2) |
O1A—C10A | 1.431 (2) | O1C—C10C | 1.431 (2) |
O1A—H1A | 0.8400 | O1C—H1C | 0.8400 |
C1A—C4A | 1.377 (3) | C1C—C4C | 1.375 (3) |
C1A—C5A | 1.456 (3) | C1C—C5C | 1.458 (3) |
C2A—C3A | 1.357 (3) | C2C—C3C | 1.361 (3) |
C2A—H2A | 0.9500 | C2C—H2C | 0.9500 |
C3A—C4A | 1.412 (3) | C3C—C4C | 1.417 (3) |
C3A—H3A | 0.9500 | C3C—H3C | 0.9500 |
C4A—H4A | 0.9500 | C4C—H4C | 0.9500 |
C5A—C6A | 1.333 (2) | C5C—C6C | 1.335 (3) |
C5A—H5A | 0.9500 | C5C—H5C | 0.9500 |
C6A—C10A | 1.523 (2) | C6C—C10C | 1.519 (3) |
C7A—C8A | 1.550 (3) | C7C—C8C | 1.548 (3) |
C7A—H7A1 | 0.9900 | C7C—H7C1 | 0.9900 |
C7A—H7A2 | 0.9900 | C7C—H7C2 | 0.9900 |
C8A—C9A | 1.537 (3) | C8C—C9C | 1.535 (3) |
C8A—H8A1 | 0.9900 | C8C—H8C1 | 0.9900 |
C8A—H8A2 | 0.9900 | C8C—H8C2 | 0.9900 |
C9A—C10A | 1.530 (2) | C9C—C10C | 1.534 (3) |
C9A—C11A | 1.531 (2) | C9C—C11C | 1.534 (2) |
C9A—H9A | 1.0000 | C9C—H9C | 1.0000 |
C10A—H10A | 1.0000 | C10C—H10C | 1.0000 |
C11A—C12A | 1.549 (3) | C11C—C12C | 1.552 (3) |
C11A—H11A | 0.9900 | C11C—H11E | 0.9900 |
C11A—H11B | 0.9900 | C11C—H11F | 0.9900 |
C12A—H12A | 0.9900 | C12C—H12E | 0.9900 |
C12A—H12B | 0.9900 | C12C—H12F | 0.9900 |
S1B—C2B | 1.717 (2) | S1D—C2D | 1.718 (2) |
S1B—C1B | 1.7348 (19) | S1D—C1D | 1.7373 (19) |
N1B—C6B | 1.442 (2) | N1D—C6D | 1.438 (2) |
N1B—C12B | 1.481 (2) | N1D—C12D | 1.481 (2) |
N1B—C7B | 1.483 (2) | N1D—C7D | 1.484 (2) |
O1B—C10B | 1.435 (2) | O1D—C10D | 1.430 (2) |
O1B—H1B | 0.8400 | O1D—H1D | 0.8400 |
C1B—C4B | 1.377 (3) | C1D—C4D | 1.372 (3) |
C1B—C5B | 1.455 (3) | C1D—C5D | 1.451 (3) |
C2B—C3B | 1.354 (3) | C2D—C3D | 1.360 (3) |
C2B—H2B | 0.9500 | C2D—H2D | 0.9500 |
C3B—C4B | 1.420 (3) | C3D—C4D | 1.415 (3) |
C3B—H3B | 0.9500 | C3D—H3D | 0.9500 |
C4B—H4B | 0.9500 | C4D—H4D | 0.9500 |
C5B—C6B | 1.333 (3) | C5D—C6D | 1.332 (3) |
C5B—H5B | 0.9500 | C5D—H5D | 0.9500 |
C6B—C10B | 1.516 (2) | C6D—C10D | 1.522 (2) |
C7B—C8B | 1.549 (3) | C7D—C8D | 1.551 (3) |
C7B—H7B1 | 0.9900 | C7D—H7D1 | 0.9900 |
C7B—H7B2 | 0.9900 | C7D—H7D2 | 0.9900 |
C8B—C9B | 1.538 (2) | C8D—C9D | 1.538 (3) |
C8B—H8B1 | 0.9900 | C8D—H8D1 | 0.9900 |
C8B—H8B2 | 0.9900 | C8D—H8D2 | 0.9900 |
C9B—C10B | 1.530 (3) | C9D—C11D | 1.532 (3) |
C9B—C11B | 1.533 (3) | C9D—C10D | 1.534 (3) |
C9B—H9B | 1.0000 | C9D—H9D | 1.0000 |
C10B—H10B | 1.0000 | C10D—H10D | 1.0000 |
C11B—C12B | 1.545 (2) | C11D—C12D | 1.548 (3) |
C11B—H11C | 0.9900 | C11D—H11G | 0.9900 |
C11B—H11D | 0.9900 | C11D—H11H | 0.9900 |
C12B—H12C | 0.9900 | C12D—H12G | 0.9900 |
C12B—H12D | 0.9900 | C12D—H12H | 0.9900 |
C2A—S1A—C1A | 91.66 (9) | C2C—S1C—C1C | 91.60 (10) |
C6A—N1A—C7A | 107.28 (14) | C6C—N1C—C12C | 108.88 (14) |
C6A—N1A—C12A | 109.25 (15) | C6C—N1C—C7C | 107.69 (14) |
C7A—N1A—C12A | 108.86 (14) | C12C—N1C—C7C | 108.94 (14) |
C10A—O1A—H1A | 109.5 | C10C—O1C—H1C | 109.5 |
C4A—C1A—C5A | 125.21 (18) | C4C—C1C—C5C | 124.91 (18) |
C4A—C1A—S1A | 110.39 (14) | C4C—C1C—S1C | 110.58 (15) |
C5A—C1A—S1A | 124.39 (14) | C5C—C1C—S1C | 124.48 (14) |
C3A—C2A—S1A | 112.08 (15) | C3C—C2C—S1C | 112.39 (15) |
C3A—C2A—H2A | 124.0 | C3C—C2C—H2C | 123.8 |
S1A—C2A—H2A | 124.0 | S1C—C2C—H2C | 123.8 |
C2A—C3A—C4A | 112.69 (18) | C2C—C3C—C4C | 112.26 (18) |
C2A—C3A—H3A | 123.7 | C2C—C3C—H3C | 123.9 |
C4A—C3A—H3A | 123.7 | C4C—C3C—H3C | 123.9 |
C1A—C4A—C3A | 113.17 (18) | C1C—C4C—C3C | 113.17 (18) |
C1A—C4A—H4A | 123.4 | C1C—C4C—H4C | 123.4 |
C3A—C4A—H4A | 123.4 | C3C—C4C—H4C | 123.4 |
C6A—C5A—C1A | 126.55 (17) | C6C—C5C—C1C | 126.38 (18) |
C6A—C5A—H5A | 116.7 | C6C—C5C—H5C | 116.8 |
C1A—C5A—H5A | 116.7 | C1C—C5C—H5C | 116.8 |
C5A—C6A—N1A | 120.69 (16) | C5C—C6C—N1C | 120.39 (17) |
C5A—C6A—C10A | 125.26 (17) | C5C—C6C—C10C | 125.30 (17) |
N1A—C6A—C10A | 114.02 (15) | N1C—C6C—C10C | 114.31 (15) |
N1A—C7A—C8A | 111.32 (15) | N1C—C7C—C8C | 111.46 (15) |
N1A—C7A—H7A1 | 109.4 | N1C—C7C—H7C1 | 109.3 |
C8A—C7A—H7A1 | 109.4 | C8C—C7C—H7C1 | 109.3 |
N1A—C7A—H7A2 | 109.4 | N1C—C7C—H7C2 | 109.3 |
C8A—C7A—H7A2 | 109.4 | C8C—C7C—H7C2 | 109.3 |
H7A1—C7A—H7A2 | 108.0 | H7C1—C7C—H7C2 | 108.0 |
C9A—C8A—C7A | 108.52 (15) | C9C—C8C—C7C | 108.45 (15) |
C9A—C8A—H8A1 | 110.0 | C9C—C8C—H8C1 | 110.0 |
C7A—C8A—H8A1 | 110.0 | C7C—C8C—H8C1 | 110.0 |
C9A—C8A—H8A2 | 110.0 | C9C—C8C—H8C2 | 110.0 |
C7A—C8A—H8A2 | 110.0 | C7C—C8C—H8C2 | 110.0 |
H8A1—C8A—H8A2 | 108.4 | H8C1—C8C—H8C2 | 108.4 |
C10A—C9A—C11A | 107.41 (15) | C10C—C9C—C11C | 107.67 (15) |
C10A—C9A—C8A | 110.11 (15) | C10C—C9C—C8C | 110.16 (15) |
C11A—C9A—C8A | 108.05 (15) | C11C—C9C—C8C | 107.87 (15) |
C10A—C9A—H9A | 110.4 | C10C—C9C—H9C | 110.4 |
C11A—C9A—H9A | 110.4 | C11C—C9C—H9C | 110.4 |
C8A—C9A—H9A | 110.4 | C8C—C9C—H9C | 110.4 |
O1A—C10A—C6A | 112.68 (14) | O1C—C10C—C6C | 113.42 (15) |
O1A—C10A—C9A | 113.84 (14) | O1C—C10C—C9C | 114.06 (15) |
C6A—C10A—C9A | 107.16 (15) | C6C—C10C—C9C | 107.20 (15) |
O1A—C10A—H10A | 107.6 | O1C—C10C—H10C | 107.3 |
C6A—C10A—H10A | 107.6 | C6C—C10C—H10C | 107.3 |
C9A—C10A—H10A | 107.6 | C9C—C10C—H10C | 107.3 |
C9A—C11A—C12A | 107.79 (14) | C9C—C11C—C12C | 107.51 (14) |
C9A—C11A—H11A | 110.1 | C9C—C11C—H11E | 110.2 |
C12A—C11A—H11A | 110.1 | C12C—C11C—H11E | 110.2 |
C9A—C11A—H11B | 110.1 | C9C—C11C—H11F | 110.2 |
C12A—C11A—H11B | 110.1 | C12C—C11C—H11F | 110.2 |
H11A—C11A—H11B | 108.5 | H11E—C11C—H11F | 108.5 |
N1A—C12A—C11A | 112.05 (14) | N1C—C12C—C11C | 112.22 (14) |
N1A—C12A—H12A | 109.2 | N1C—C12C—H12E | 109.2 |
C11A—C12A—H12A | 109.2 | C11C—C12C—H12E | 109.2 |
N1A—C12A—H12B | 109.2 | N1C—C12C—H12F | 109.2 |
C11A—C12A—H12B | 109.2 | C11C—C12C—H12F | 109.2 |
H12A—C12A—H12B | 107.9 | H12E—C12C—H12F | 107.9 |
C2B—S1B—C1B | 91.69 (10) | C2D—S1D—C1D | 91.77 (10) |
C6B—N1B—C12B | 109.03 (14) | C6D—N1D—C12D | 108.30 (14) |
C6B—N1B—C7B | 107.48 (14) | C6D—N1D—C7D | 108.19 (15) |
C12B—N1B—C7B | 108.64 (14) | C12D—N1D—C7D | 108.65 (15) |
C10B—O1B—H1B | 109.5 | C10D—O1D—H1D | 109.5 |
C4B—C1B—C5B | 124.91 (18) | C4D—C1D—C5D | 125.18 (17) |
C4B—C1B—S1B | 110.36 (15) | C4D—C1D—S1D | 110.13 (14) |
C5B—C1B—S1B | 124.72 (14) | C5D—C1D—S1D | 124.67 (14) |
C3B—C2B—S1B | 112.43 (16) | C3D—C2D—S1D | 112.20 (15) |
C3B—C2B—H2B | 123.8 | C3D—C2D—H2D | 123.9 |
S1B—C2B—H2B | 123.8 | S1D—C2D—H2D | 123.9 |
C2B—C3B—C4B | 112.31 (18) | C2D—C3D—C4D | 112.14 (18) |
C2B—C3B—H3B | 123.8 | C2D—C3D—H3D | 123.9 |
C4B—C3B—H3B | 123.8 | C4D—C3D—H3D | 123.9 |
C1B—C4B—C3B | 113.21 (19) | C1D—C4D—C3D | 113.75 (18) |
C1B—C4B—H4B | 123.4 | C1D—C4D—H4D | 123.1 |
C3B—C4B—H4B | 123.4 | C3D—C4D—H4D | 123.1 |
C6B—C5B—C1B | 127.41 (17) | C6D—C5D—C1D | 127.25 (17) |
C6B—C5B—H5B | 116.3 | C6D—C5D—H5D | 116.4 |
C1B—C5B—H5B | 116.3 | C1D—C5D—H5D | 116.4 |
C5B—C6B—N1B | 120.61 (16) | C5D—C6D—N1D | 120.46 (17) |
C5B—C6B—C10B | 125.22 (17) | C5D—C6D—C10D | 125.02 (17) |
N1B—C6B—C10B | 114.17 (15) | N1D—C6D—C10D | 114.52 (15) |
N1B—C7B—C8B | 111.49 (14) | N1D—C7D—C8D | 111.82 (15) |
N1B—C7B—H7B1 | 109.3 | N1D—C7D—H7D1 | 109.3 |
C8B—C7B—H7B1 | 109.3 | C8D—C7D—H7D1 | 109.3 |
N1B—C7B—H7B2 | 109.3 | N1D—C7D—H7D2 | 109.3 |
C8B—C7B—H7B2 | 109.3 | C8D—C7D—H7D2 | 109.3 |
H7B1—C7B—H7B2 | 108.0 | H7D1—C7D—H7D2 | 107.9 |
C9B—C8B—C7B | 108.55 (15) | C9D—C8D—C7D | 108.16 (15) |
C9B—C8B—H8B1 | 110.0 | C9D—C8D—H8D1 | 110.1 |
C7B—C8B—H8B1 | 110.0 | C7D—C8D—H8D1 | 110.1 |
C9B—C8B—H8B2 | 110.0 | C9D—C8D—H8D2 | 110.1 |
C7B—C8B—H8B2 | 110.0 | C7D—C8D—H8D2 | 110.1 |
H8B1—C8B—H8B2 | 108.4 | H8D1—C8D—H8D2 | 108.4 |
C10B—C9B—C11B | 107.87 (15) | C11D—C9D—C10D | 107.90 (15) |
C10B—C9B—C8B | 109.66 (15) | C11D—C9D—C8D | 108.10 (15) |
C11B—C9B—C8B | 107.56 (15) | C10D—C9D—C8D | 109.45 (15) |
C10B—C9B—H9B | 110.6 | C11D—C9D—H9D | 110.4 |
C11B—C9B—H9B | 110.6 | C10D—C9D—H9D | 110.4 |
C8B—C9B—H9B | 110.6 | C8D—C9D—H9D | 110.4 |
O1B—C10B—C6B | 113.49 (15) | O1D—C10D—C6D | 113.23 (15) |
O1B—C10B—C9B | 113.60 (15) | O1D—C10D—C9D | 113.75 (15) |
C6B—C10B—C9B | 107.66 (14) | C6D—C10D—C9D | 107.33 (14) |
O1B—C10B—H10B | 107.2 | O1D—C10D—H10D | 107.4 |
C6B—C10B—H10B | 107.2 | C6D—C10D—H10D | 107.4 |
C9B—C10B—H10B | 107.2 | C9D—C10D—H10D | 107.4 |
C9B—C11B—C12B | 108.04 (15) | C9D—C11D—C12D | 108.27 (15) |
C9B—C11B—H11C | 110.1 | C9D—C11D—H11G | 110.0 |
C12B—C11B—H11C | 110.1 | C12D—C11D—H11G | 110.0 |
C9B—C11B—H11D | 110.1 | C9D—C11D—H11H | 110.0 |
C12B—C11B—H11D | 110.1 | C12D—C11D—H11H | 110.0 |
H11C—C11B—H11D | 108.4 | H11G—C11D—H11H | 108.4 |
N1B—C12B—C11B | 112.18 (15) | N1D—C12D—C11D | 111.89 (15) |
N1B—C12B—H12C | 109.2 | N1D—C12D—H12G | 109.2 |
C11B—C12B—H12C | 109.2 | C11D—C12D—H12G | 109.2 |
N1B—C12B—H12D | 109.2 | N1D—C12D—H12H | 109.2 |
C11B—C12B—H12D | 109.2 | C11D—C12D—H12H | 109.2 |
H12C—C12B—H12D | 107.9 | H12G—C12D—H12H | 107.9 |
C2A—S1A—C1A—C4A | 0.63 (15) | C2C—S1C—C1C—C4C | −0.41 (15) |
C2A—S1A—C1A—C5A | 179.96 (16) | C2C—S1C—C1C—C5C | 177.82 (16) |
C1A—S1A—C2A—C3A | −1.00 (16) | C1C—S1C—C2C—C3C | 0.08 (16) |
S1A—C2A—C3A—C4A | 1.1 (2) | S1C—C2C—C3C—C4C | 0.3 (2) |
C5A—C1A—C4A—C3A | −179.45 (17) | C5C—C1C—C4C—C3C | −177.59 (17) |
S1A—C1A—C4A—C3A | −0.1 (2) | S1C—C1C—C4C—C3C | 0.6 (2) |
C2A—C3A—C4A—C1A | −0.6 (3) | C2C—C3C—C4C—C1C | −0.6 (2) |
C4A—C1A—C5A—C6A | 170.67 (19) | C4C—C1C—C5C—C6C | 173.41 (19) |
S1A—C1A—C5A—C6A | −8.6 (3) | S1C—C1C—C5C—C6C | −4.6 (3) |
C1A—C5A—C6A—N1A | 2.2 (3) | C1C—C5C—C6C—N1C | 2.9 (3) |
C1A—C5A—C6A—C10A | −179.73 (17) | C1C—C5C—C6C—C10C | −178.20 (17) |
C7A—N1A—C6A—C5A | 111.00 (18) | C12C—N1C—C6C—C5C | −128.63 (18) |
C12A—N1A—C6A—C5A | −131.14 (18) | C7C—N1C—C6C—C5C | 113.38 (19) |
C7A—N1A—C6A—C10A | −67.25 (18) | C12C—N1C—C6C—C10C | 52.37 (19) |
C12A—N1A—C6A—C10A | 50.61 (19) | C7C—N1C—C6C—C10C | −65.61 (19) |
C6A—N1A—C7A—C8A | 55.71 (19) | C6C—N1C—C7C—C8C | 56.25 (19) |
C12A—N1A—C7A—C8A | −62.40 (19) | C12C—N1C—C7C—C8C | −61.69 (19) |
N1A—C7A—C8A—C9A | 5.5 (2) | N1C—C7C—C8C—C9C | 4.2 (2) |
C7A—C8A—C9A—C10A | −60.27 (19) | C7C—C8C—C9C—C10C | −59.53 (19) |
C7A—C8A—C9A—C11A | 56.76 (19) | C7C—C8C—C9C—C11C | 57.73 (19) |
C5A—C6A—C10A—O1A | −40.2 (2) | C5C—C6C—C10C—O1C | −42.3 (3) |
N1A—C6A—C10A—O1A | 137.97 (15) | N1C—C6C—C10C—O1C | 136.65 (16) |
C5A—C6A—C10A—C9A | −166.16 (17) | C5C—C6C—C10C—C9C | −169.10 (17) |
N1A—C6A—C10A—C9A | 12.0 (2) | N1C—C6C—C10C—C9C | 9.8 (2) |
C11A—C9A—C10A—O1A | 168.29 (15) | C11C—C9C—C10C—O1C | 168.46 (15) |
C8A—C9A—C10A—O1A | −74.29 (19) | C8C—C9C—C10C—O1C | −74.16 (19) |
C11A—C9A—C10A—C6A | −66.43 (18) | C11C—C9C—C10C—C6C | −65.10 (18) |
C8A—C9A—C10A—C6A | 51.00 (18) | C8C—C9C—C10C—C6C | 52.28 (19) |
C10A—C9A—C11A—C12A | 55.25 (19) | C10C—C9C—C11C—C12C | 55.40 (19) |
C8A—C9A—C11A—C12A | −63.51 (19) | C8C—C9C—C11C—C12C | −63.46 (19) |
C6A—N1A—C12A—C11A | −61.5 (2) | C6C—N1C—C12C—C11C | −61.6 (2) |
C7A—N1A—C12A—C11A | 55.3 (2) | C7C—N1C—C12C—C11C | 55.6 (2) |
C9A—C11A—C12A—N1A | 7.0 (2) | C9C—C11C—C12C—N1C | 6.4 (2) |
C2B—S1B—C1B—C4B | 0.61 (15) | C2D—S1D—C1D—C4D | 0.42 (15) |
C2B—S1B—C1B—C5B | −178.40 (17) | C2D—S1D—C1D—C5D | 178.67 (17) |
C1B—S1B—C2B—C3B | −0.81 (17) | C1D—S1D—C2D—C3D | −0.68 (16) |
S1B—C2B—C3B—C4B | 0.8 (2) | S1D—C2D—C3D—C4D | 0.8 (2) |
C5B—C1B—C4B—C3B | 178.73 (18) | C5D—C1D—C4D—C3D | −178.31 (18) |
S1B—C1B—C4B—C3B | −0.3 (2) | S1D—C1D—C4D—C3D | −0.1 (2) |
C2B—C3B—C4B—C1B | −0.3 (3) | C2D—C3D—C4D—C1D | −0.4 (3) |
C4B—C1B—C5B—C6B | 173.55 (19) | C4D—C1D—C5D—C6D | 170.85 (19) |
S1B—C1B—C5B—C6B | −7.6 (3) | S1D—C1D—C5D—C6D | −7.1 (3) |
C1B—C5B—C6B—N1B | 0.9 (3) | C1D—C5D—C6D—N1D | 2.4 (3) |
C1B—C5B—C6B—C10B | −179.20 (17) | C1D—C5D—C6D—C10D | −176.59 (17) |
C12B—N1B—C6B—C5B | −128.06 (18) | C12D—N1D—C6D—C5D | −125.11 (18) |
C7B—N1B—C6B—C5B | 114.36 (18) | C7D—N1D—C6D—C5D | 117.29 (19) |
C12B—N1B—C6B—C10B | 52.07 (19) | C12D—N1D—C6D—C10D | 54.0 (2) |
C7B—N1B—C6B—C10B | −65.52 (18) | C7D—N1D—C6D—C10D | −63.62 (19) |
C6B—N1B—C7B—C8B | 56.04 (19) | C6D—N1D—C7D—C8D | 55.1 (2) |
C12B—N1B—C7B—C8B | −61.79 (19) | C12D—N1D—C7D—C8D | −62.3 (2) |
N1B—C7B—C8B—C9B | 4.5 (2) | N1D—C7D—C8D—C9D | 5.2 (2) |
C7B—C8B—C9B—C10B | −59.73 (19) | C7D—C8D—C9D—C11D | 56.62 (19) |
C7B—C8B—C9B—C11B | 57.32 (19) | C7D—C8D—C9D—C10D | −60.66 (19) |
C5B—C6B—C10B—O1B | −43.6 (2) | C5D—C6D—C10D—O1D | −46.9 (2) |
N1B—C6B—C10B—O1B | 136.29 (15) | N1D—C6D—C10D—O1D | 134.07 (16) |
C5B—C6B—C10B—C9B | −170.19 (17) | C5D—C6D—C10D—C9D | −173.26 (18) |
N1B—C6B—C10B—C9B | 9.7 (2) | N1D—C6D—C10D—C9D | 7.7 (2) |
C11B—C9B—C10B—O1B | 169.01 (14) | C11D—C9D—C10D—O1D | 170.63 (14) |
C8B—C9B—C10B—O1B | −74.14 (19) | C8D—C9D—C10D—O1D | −71.97 (19) |
C11B—C9B—C10B—C6B | −64.44 (18) | C11D—C9D—C10D—C6D | −63.32 (18) |
C8B—C9B—C10B—C6B | 52.42 (19) | C8D—C9D—C10D—C6D | 54.09 (19) |
C10B—C9B—C11B—C12B | 54.84 (19) | C10D—C9D—C11D—C12D | 55.07 (19) |
C8B—C9B—C11B—C12B | −63.37 (19) | C8D—C9D—C11D—C12D | −63.20 (19) |
C6B—N1B—C12B—C11B | −61.27 (19) | C6D—N1D—C12D—C11D | −61.81 (19) |
C7B—N1B—C12B—C11B | 55.58 (19) | C7D—N1D—C12D—C11D | 55.49 (19) |
C9B—C11B—C12B—N1B | 6.5 (2) | C9D—C11D—C12D—N1D | 6.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O1B | 0.84 | 1.97 | 2.7734 (18) | 161 |
O1B—H1B···O1C | 0.84 | 2.02 | 2.8124 (18) | 157 |
O1C—H1C···O1D | 0.84 | 1.97 | 2.7812 (18) | 163 |
O1D—H1D···O1A | 0.84 | 1.97 | 2.7795 (18) | 162 |
Experimental details
Crystal data | |
Chemical formula | C12H15NOS |
Mr | 221.32 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 90 |
a, b, c (Å) | 14.7933 (3), 20.0349 (4), 14.8243 (3) |
β (°) | 90.2820 (7) |
V (Å3) | 4393.61 (15) |
Z | 16 |
Radiation type | Mo Kα |
µ (mm−1) | 0.27 |
Crystal size (mm) | 0.38 × 0.35 × 0.03 |
Data collection | |
Diffractometer | Nonius KappaCCD area-detector diffractometer |
Absorption correction | Multi-scan (SCALEPACK; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.906, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 37339, 10043, 7113 |
Rint | 0.058 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.114, 1.04 |
No. of reflections | 10043 |
No. of parameters | 545 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.34 |
Computer programs: COLLECT (Nonius, 1999), SCALEPACK (Otwinowski & Minor, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL (Sheldrick, 1995), SHELX97 and local procedures.
S1A—C1A | 1.7350 (19) | S1C—C1C | 1.7357 (19) |
O1A—C10A | 1.431 (2) | O1C—C10C | 1.431 (2) |
C6A—C10A | 1.523 (2) | C6C—C10C | 1.519 (3) |
S1B—C1B | 1.7348 (19) | S1D—C1D | 1.7373 (19) |
O1B—C10B | 1.435 (2) | O1D—C10D | 1.430 (2) |
C6B—C10B | 1.516 (2) | C6D—C10D | 1.522 (2) |
C6A—C5A—C1A | 126.55 (17) | C6C—C5C—C1C | 126.38 (18) |
C5A—C6A—C10A | 125.26 (17) | C5C—C6C—C10C | 125.30 (17) |
N1A—C6A—C10A | 114.02 (15) | N1C—C6C—C10C | 114.31 (15) |
C6B—C5B—C1B | 127.41 (17) | C6D—C5D—C1D | 127.25 (17) |
C5B—C6B—C10B | 125.22 (17) | C5D—C6D—C10D | 125.02 (17) |
N1B—C6B—C10B | 114.17 (15) | N1D—C6D—C10D | 114.52 (15) |
S1A—C1A—C5A—C6A | −8.6 (3) | S1C—C1C—C5C—C6C | −4.6 (3) |
S1B—C1B—C5B—C6B | −7.6 (3) | S1D—C1D—C5D—C6D | −7.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O1B | 0.84 | 1.97 | 2.7734 (18) | 160.5 |
O1B—H1B···O1C | 0.84 | 2.02 | 2.8124 (18) | 156.7 |
O1C—H1C···O1D | 0.84 | 1.97 | 2.7812 (18) | 163.2 |
O1D—H1D···O1A | 0.84 | 1.97 | 2.7795 (18) | 162.4 |
Radiation therapy prevents cancer cells from growing and dividing, but can also damage normal cells. Radio-sensitizers are drugs that sensitize cancer cells to radiation therapy. Recent research in our laboratory has focused on the discovery of molecules that can either sensitize a tumour to radiation without affecting healthy tissue, or that can shield normal cells from radiation damage. Recently, we have reported (Sekhar et al., 2007) the radio-sensitizing activity of N-arylsubstituted rac-(Z)-2-(1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-ols. In addition to these indole analogues, we have also synthesized 1-azabicyclo[2.2.2]octan-3-ols linked to non-indolic systems, in order to compare their radio-sensitizing activities with those of the indole analogues. The title compound, (I), was prepared by the base-catalyzed reaction of thiophene-2-carboxaldehyde with 1-azabicyclo[2.2.2]octan-3-one and subsequent reduction to the corresponding secondary alcohol. In order to confirm the double-bond geometry, and to determine the molecular conformation in the crystal structure, the X-ray analysis of compound (I) has been carried out, and the results are presented here.
The asymmetric unit of (I) contains four crystallographically independent molecules, (IA)–(ID), with almost identical bond lengths and angles. The molecular structure and atom-numbering scheme of molecule (IA) are shown in Fig. 1, and selected bond lengths and angles are listed in Table 1.
The title molecule comprises a 1-azabicyclo[2.2.2]octan-3-ol moiety and a 2-thienyl group linked by a C5═C6 bond that has Z geometry. In this (Z) isomer, the C1—C5 bond is in the trans position with respect to the C6—C10 bond. The double bond has a nearly planar atomic arrangement, since the r.m.s. deviation from the best plane passing through atoms N1, C6, C10, C5 and C1 is 0.0061 (10) Å for (IA), 0.0972 (10) Å for (IB), 0.1943 (10) Å for (IC) and 0.2500 (10) Å for (ID). The geometries of the four molecules in the asymmetric unit are essentially the same, so only molecule A is discussed in detail here.
The bond angles around atoms C5A and C6A deviate from 120° and this is in general agreement with our earlier observation for a similar type of compound (Sonar et al., 2004). The angles N1A—C6A—C10A, C6A═C5A—C1A and C5A═C6A—C10A [114.02 (15), 126.55 (17) and 125.26 (17)°, respectively] are distorted as a consequence of the strain induced by the double-bond linkage at C5A═C6A. The azabicyclic system exhibits small distortions in geometry compared with standard tetrahedral values. The bond angles C6A—N1A—C7A, C10A—C9A—C11A and C9A—C11A—C12A [107.28 (14), 107.41 (15) and 107.79 (14)°, respectively] are, on average, smaller than the ideal tetrahedral value of 109.5°, while the bond angles N1A—C7A—C8A, O1A—C10A—C9A and N1A—C12A—C11A [111.32 (15), 113.84 (14) and 112.05 (14)°, respectively] are, on average, slightly larger than the tetrahedral value. The C4═C1—C5═C6 torsion angles [170.67 (19), 173.55 (19), 173.41 (19) and 170.85 (19)° for molecules A, B, C and D, respectively] indicate a deviation of the 2-thienyl ring from the plane of the double bond connected to the azabicyclic ring in these molecules. This small deviation facilitates a weak conjugation between the C5═C6 double bond and the 2-thienyl ring. This is also evident from the C1—C5 bond lengths [1.456 (3), 1.455 (3), 1.458 (3) and 1.451 (3) Å in molecules A, B, C and D, respectively].
Strong hydrogen bonds and weaker C—H···π interactions (Fig. 2) present in the crystal structure of (I) effectively group sets of four molecules together into roughly cylindrical units. Within each group, all molecules possess the same absolute configuration and are related to other groups of opposite hand via crystallographic inversion centres. The donor–acceptor direction of the R44(8) hydrogen-bonded motif comprising O1A—H1A···O1B—H1B···O1C—H1C···O1D—H1D···O1A (Table 2) is opposite from the directionality around the C—H···π linked thienyl rings (ringA—H4A···ringD—H4D···ringC—H4C···ringB—H4B···ringA). These C—H···π interactions, C4A···ringB, C4B···ringC, C4C···ringD and C4D···ringA with distances of 3.551 (2), 3.531 (2), 3.554 (2) and 3.565 (2) Å, respectively, effectively lock the thiophene rings into a single conformation. Dihedral angles between successive rings are A/B = 89.24 (4), B/C = 86.64 (4), C/D = 85.08 (4) and D/A = 87.39 (4)°.