organic compounds
The crystal structure of the title compound is composed of diastereomers of 4-(2-hydroxyphenyl)-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine, C21H19NOS, that are cocrystallized. The asymmetric unit contains two molecules. One S and two C atoms of the heterocyclic ring in one molecule are disordered, resulting in two different conformers. The H atoms at the chiral centers in the ordered molecule are trans with respect to each other, cis in the other conformer. The average bond distances are: S-Csp3 1.825 (2), S-Csp2 1.778 (8), N-Csp3 1.495 (5), N-Csp2 1.415 (8), O-Caromatic 1.380 (7), Csp3-Csp3 1.533 (14), Csp3-Caromatic 1.52 (2) and C-Caromatic 1.382 (13) Å. The structure is stabilized by strong intra- and intermolecular hydrogen bonds.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802004580/cv6096sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802004580/cv6096Isup2.hkl |
CCDC reference: 183800
Computing details top
Data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
2-Phenyl-4-(2'-hydroxyphenyl)-2,3,4,5-tetrahydro-1,5-benzothiazepine top
Crystal data top
C21H19NOS | Dx = 1.291 Mg m−3 |
Mr = 333.43 | Melting point: 363 K K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
a = 10.3404 (1) Å | Cell parameters from 12187 reflections |
b = 36.9797 (7) Å | θ = 1.0–27.5° |
c = 9.4929 (1) Å | µ = 0.20 mm−1 |
β = 108.993 (1)° | T = 170 K |
V = 3432.32 (8) Å3 | Block, colourless |
Z = 8 | 0.15 × 0.15 × 0.15 mm |
F(000) = 1408 |
Data collection top
Nonius KappaCCD diffractometer | 7825 independent reflections |
Radiation source: fine-focus sealed tube | 3496 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.088 |
ω and φ scans | θmax = 27.6°, θmin = 3.9° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −13→13 |
Tmin = 0.97, Tmax = 0.97 | k = −47→47 |
23647 measured reflections | l = −12→11 |
Refinement top
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)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.051P)2] where P = (Fo2 + 2Fc2)/3 |
7825 reflections | (Δ/σ)max < 0.001 |
456 parameters | Δρmax = 0.45 e Å−3 |
14 restraints | Δρmin = −0.53 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1A | 0.4879 (3) | 0.38069 (9) | 0.1634 (3) | 0.0326 (8) | |
C2A | 0.3908 (3) | 0.35310 (9) | 0.1420 (3) | 0.0341 (8) | |
S3A | 0.28795 (9) | 0.33514 (2) | −0.03227 (9) | 0.0394 (3) | |
C4A | 0.3962 (3) | 0.33867 (8) | −0.1496 (3) | 0.0297 (8) | |
H4A | 0.4919 | 0.3321 | −0.0889 | 0.036* | |
C5A | 0.3964 (3) | 0.37692 (8) | −0.2106 (3) | 0.0309 (8) | |
H5A1 | 0.4720 | 0.3790 | −0.2528 | 0.037* | |
H5A2 | 0.3095 | 0.3809 | −0.2927 | 0.037* | |
C6A | 0.4127 (3) | 0.40652 (8) | −0.0943 (3) | 0.0284 (8) | |
H6A | 0.3248 | 0.4086 | −0.0722 | 0.034* | |
N7A | 0.5229 (3) | 0.39685 (8) | 0.0465 (3) | 0.0336 (7) | |
H7A | 0.572 (3) | 0.4136 (9) | 0.074 (4) | 0.044 (6)* | |
C8A | 0.5594 (3) | 0.39159 (9) | 0.3098 (3) | 0.0405 (9) | |
H8A | 0.6282 | 0.4096 | 0.3266 | 0.049* | |
C9A | 0.5311 (4) | 0.37639 (12) | 0.4303 (4) | 0.0502 (10) | |
H9A | 0.5786 | 0.3846 | 0.5284 | 0.060* | |
C10A | 0.4351 (4) | 0.34965 (11) | 0.4081 (4) | 0.0522 (10) | |
H10A | 0.4155 | 0.3394 | 0.4907 | 0.063* | |
C11A | 0.3665 (4) | 0.33749 (10) | 0.2653 (4) | 0.0458 (9) | |
H11A | 0.3023 | 0.3183 | 0.2509 | 0.055* | |
C12A | 0.3437 (3) | 0.31110 (9) | −0.2733 (3) | 0.0305 (8) | |
C13A | 0.2100 (3) | 0.31377 (9) | −0.3726 (3) | 0.0408 (9) | |
H13A | 0.1506 | 0.3320 | −0.3583 | 0.049* | |
C14A | 0.1638 (4) | 0.29012 (10) | −0.4911 (4) | 0.0463 (9) | |
H14A | 0.0733 | 0.2923 | −0.5584 | 0.056* | |
C15A | 0.2485 (4) | 0.26344 (10) | −0.5120 (4) | 0.0500 (10) | |
H15A | 0.2168 | 0.2474 | −0.5942 | 0.060* | |
C16A | 0.3789 (4) | 0.26016 (10) | −0.4137 (4) | 0.0509 (10) | |
H16A | 0.4373 | 0.2416 | −0.4276 | 0.061* | |
C17A | 0.4262 (4) | 0.28386 (9) | −0.2936 (3) | 0.0408 (9) | |
H17A | 0.5162 | 0.2811 | −0.2253 | 0.049* | |
C18A | 0.4436 (3) | 0.44280 (9) | −0.1488 (3) | 0.0302 (8) | |
C19A | 0.5520 (3) | 0.44664 (9) | −0.2033 (3) | 0.0384 (9) | |
H19A | 0.6069 | 0.4261 | −0.2048 | 0.046* | |
C20A | 0.5828 (4) | 0.47933 (10) | −0.2556 (3) | 0.0443 (9) | |
H20A | 0.6581 | 0.4814 | −0.2917 | 0.053* | |
C21A | 0.5019 (4) | 0.50898 (10) | −0.2543 (3) | 0.0445 (9) | |
H21A | 0.5210 | 0.5315 | −0.2914 | 0.053* | |
C22A | 0.3945 (3) | 0.50632 (9) | −0.2001 (3) | 0.0381 (8) | |
H22A | 0.3392 | 0.5269 | −0.2005 | 0.046* | |
C23A | 0.3668 (3) | 0.47345 (9) | −0.1444 (3) | 0.0313 (8) | |
O24A | 0.2619 (2) | 0.47023 (6) | −0.0857 (2) | 0.0407 (6) | |
H24A | 0.230 (3) | 0.4894 (9) | −0.070 (3) | 0.044 (6)* | |
C1B | −0.0430 (3) | 0.40185 (9) | −0.2248 (3) | 0.0306 (8) | |
C2B | −0.1259 (3) | 0.37147 (8) | −0.2642 (3) | 0.0308 (8) | |
S3B | −0.2192 (3) | 0.35023 (7) | −0.1613 (3) | 0.0374 (6) | 0.663 (4) |
C4B | −0.0783 (4) | 0.34177 (12) | 0.0111 (4) | 0.0380 (14) | 0.663 (4) |
H4B | 0.0008 | 0.3307 | −0.0118 | 0.046* | 0.663 (4) |
C5B | −0.0321 (5) | 0.37565 (11) | 0.1072 (5) | 0.0365 (13) | 0.663 (4) |
H5B1 | 0.0222 | 0.3678 | 0.2089 | 0.044* | 0.663 (4) |
H5B2 | −0.1148 | 0.3879 | 0.1144 | 0.044* | 0.663 (4) |
S3B' | −0.2268 (6) | 0.36301 (13) | −0.1459 (6) | 0.0374 (6) | 0.337 (4) |
C4B' | −0.1254 (7) | 0.3555 (2) | 0.0491 (8) | 0.0380 (14) | 0.337 (4) |
H4B' | −0.1582 | 0.3721 | 0.1137 | 0.046* | 0.337 (4) |
C5B' | 0.0246 (8) | 0.36410 (14) | 0.0683 (12) | 0.0365 (13) | 0.337 (4) |
H5B3 | 0.0824 | 0.3554 | 0.1673 | 0.044* | 0.337 (4) |
H5B4 | 0.0513 | 0.3505 | −0.0079 | 0.044* | 0.337 (4) |
C6B | 0.0541 (3) | 0.40413 (8) | 0.0550 (3) | 0.0368 (8) | |
H6B | 0.1408 | 0.3931 | 0.0499 | 0.044* | |
N7B | −0.0248 (3) | 0.42149 (8) | −0.0907 (3) | 0.0355 (7) | |
H7B | 0.016 (3) | 0.4394 (9) | −0.091 (3) | 0.044 (6)* | |
C8B | 0.0195 (3) | 0.41451 (9) | −0.3261 (3) | 0.0398 (9) | |
H8B | 0.0794 | 0.4347 | −0.2997 | 0.048* | |
C9B | −0.0037 (3) | 0.39847 (11) | −0.4622 (4) | 0.0482 (10) | |
H9B | 0.0367 | 0.4082 | −0.5307 | 0.058* | |
C10B | −0.0848 (4) | 0.36852 (12) | −0.4993 (4) | 0.0499 (10) | |
H10B | −0.1009 | 0.3573 | −0.5936 | 0.060* | |
C11B | −0.1435 (3) | 0.35454 (9) | −0.4000 (4) | 0.0415 (9) | |
H11B | −0.1965 | 0.3331 | −0.4246 | 0.050* | |
C12B | −0.1347 (4) | 0.31558 (12) | 0.0980 (3) | 0.0517 (11) | |
C13B | −0.0672 (4) | 0.28232 (17) | 0.1079 (4) | 0.0703 (15) | |
H13B | 0.0061 | 0.2799 | 0.0688 | 0.084* | |
C14B | −0.1063 (5) | 0.25342 (14) | 0.1735 (5) | 0.0769 (14) | |
H14B | −0.0604 | 0.2310 | 0.1787 | 0.092* | |
C15B | −0.2088 (5) | 0.25622 (12) | 0.2309 (4) | 0.0622 (12) | |
H15B | −0.2342 | 0.2358 | 0.2768 | 0.075* | |
C16B | −0.2767 (4) | 0.28828 (12) | 0.2237 (4) | 0.0513 (10) | |
H16B | −0.3488 | 0.2903 | 0.2649 | 0.062* | |
C17B | −0.2400 (3) | 0.31747 (10) | 0.1566 (4) | 0.0451 (9) | |
H17B | −0.2884 | 0.3396 | 0.1503 | 0.054* | |
C18B | 0.0837 (3) | 0.43223 (8) | 0.1766 (3) | 0.0287 (8) | |
C19B | 0.2088 (3) | 0.43147 (9) | 0.2911 (3) | 0.0336 (8) | |
H19B | 0.2752 | 0.4141 | 0.2875 | 0.040* | |
C20B | 0.2393 (4) | 0.45521 (10) | 0.4096 (3) | 0.0451 (9) | |
H20B | 0.3250 | 0.4539 | 0.4870 | 0.054* | |
C21B | 0.1444 (4) | 0.48066 (10) | 0.4143 (4) | 0.0515 (10) | |
H21B | 0.1646 | 0.4974 | 0.4946 | 0.062* | |
C22B | 0.0198 (4) | 0.48208 (10) | 0.3029 (4) | 0.0569 (11) | |
H22B | −0.0456 | 0.4998 | 0.3066 | 0.068* | |
C23B | −0.0106 (3) | 0.45784 (10) | 0.1853 (3) | 0.0403 (9) | |
O24B | −0.1399 (3) | 0.46032 (8) | 0.0790 (3) | 0.0557 (8) | |
H24B | −0.146 (3) | 0.4485 (9) | 0.010 (3) | 0.044 (6)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
C1A | 0.039 (2) | 0.032 (2) | 0.0296 (19) | 0.0133 (17) | 0.0151 (16) | 0.0081 (16) |
C2A | 0.044 (2) | 0.030 (2) | 0.0334 (19) | 0.0110 (17) | 0.0185 (16) | 0.0051 (16) |
S3A | 0.0553 (6) | 0.0288 (5) | 0.0403 (5) | −0.0049 (4) | 0.0240 (4) | −0.0016 (4) |
C4A | 0.0367 (19) | 0.0235 (19) | 0.0298 (18) | 0.0002 (15) | 0.0120 (15) | −0.0007 (15) |
C5A | 0.0359 (19) | 0.028 (2) | 0.0281 (18) | −0.0025 (15) | 0.0097 (15) | −0.0002 (15) |
C6A | 0.0331 (18) | 0.026 (2) | 0.0237 (17) | 0.0009 (15) | 0.0061 (15) | 0.0028 (15) |
N7A | 0.0449 (19) | 0.0266 (19) | 0.0276 (16) | −0.0008 (14) | 0.0094 (14) | −0.0001 (14) |
C8A | 0.041 (2) | 0.048 (2) | 0.029 (2) | 0.0144 (18) | 0.0071 (17) | −0.0041 (18) |
C9A | 0.054 (3) | 0.067 (3) | 0.028 (2) | 0.024 (2) | 0.0112 (19) | 0.006 (2) |
C10A | 0.071 (3) | 0.058 (3) | 0.036 (2) | 0.019 (2) | 0.028 (2) | 0.017 (2) |
C11A | 0.066 (3) | 0.041 (2) | 0.039 (2) | 0.0050 (19) | 0.029 (2) | 0.0096 (18) |
C12A | 0.037 (2) | 0.024 (2) | 0.0307 (18) | −0.0036 (16) | 0.0114 (16) | 0.0028 (15) |
C13A | 0.042 (2) | 0.033 (2) | 0.045 (2) | −0.0014 (18) | 0.0118 (19) | −0.0035 (18) |
C14A | 0.048 (2) | 0.035 (2) | 0.047 (2) | −0.0058 (19) | 0.0027 (18) | −0.0059 (19) |
C15A | 0.070 (3) | 0.028 (2) | 0.046 (2) | −0.006 (2) | 0.010 (2) | −0.0072 (18) |
C16A | 0.060 (3) | 0.034 (2) | 0.050 (2) | 0.0086 (19) | 0.007 (2) | −0.009 (2) |
C17A | 0.048 (2) | 0.032 (2) | 0.036 (2) | 0.0079 (18) | 0.0062 (17) | −0.0015 (17) |
C18A | 0.037 (2) | 0.029 (2) | 0.0231 (17) | −0.0082 (16) | 0.0075 (15) | −0.0012 (15) |
C19A | 0.048 (2) | 0.030 (2) | 0.035 (2) | −0.0045 (17) | 0.0100 (17) | −0.0027 (16) |
C20A | 0.053 (2) | 0.035 (2) | 0.051 (2) | −0.0118 (19) | 0.0245 (19) | −0.0014 (19) |
C21A | 0.062 (3) | 0.031 (2) | 0.040 (2) | −0.013 (2) | 0.0169 (19) | 0.0011 (17) |
C22A | 0.048 (2) | 0.024 (2) | 0.038 (2) | −0.0034 (17) | 0.0089 (17) | −0.0004 (16) |
C23A | 0.037 (2) | 0.030 (2) | 0.0245 (18) | −0.0020 (16) | 0.0059 (15) | −0.0024 (15) |
O24A | 0.0484 (16) | 0.0297 (16) | 0.0459 (14) | 0.0021 (12) | 0.0180 (12) | −0.0041 (12) |
C1B | 0.0331 (19) | 0.031 (2) | 0.0252 (18) | 0.0018 (16) | 0.0058 (15) | −0.0039 (16) |
C2B | 0.0276 (19) | 0.032 (2) | 0.0286 (19) | 0.0032 (16) | 0.0038 (15) | 0.0027 (16) |
S3B | 0.0410 (7) | 0.0328 (16) | 0.0319 (7) | −0.0153 (11) | 0.0029 (5) | 0.0008 (10) |
C4B | 0.026 (3) | 0.062 (4) | 0.034 (3) | −0.007 (3) | 0.022 (2) | 0.001 (3) |
C5B | 0.060 (4) | 0.019 (3) | 0.025 (3) | 0.009 (2) | 0.008 (2) | −0.004 (2) |
S3B' | 0.0410 (7) | 0.0328 (16) | 0.0319 (7) | −0.0153 (11) | 0.0029 (5) | 0.0008 (10) |
C4B' | 0.026 (3) | 0.062 (4) | 0.034 (3) | −0.007 (3) | 0.022 (2) | 0.001 (3) |
C5B' | 0.060 (4) | 0.019 (3) | 0.025 (3) | 0.009 (2) | 0.008 (2) | −0.004 (2) |
C6B | 0.040 (2) | 0.034 (2) | 0.032 (2) | 0.0054 (17) | 0.0070 (16) | −0.0009 (17) |
N7B | 0.0492 (19) | 0.0273 (19) | 0.0275 (16) | −0.0037 (14) | 0.0088 (14) | −0.0010 (14) |
C8B | 0.043 (2) | 0.046 (2) | 0.0284 (19) | −0.0074 (17) | 0.0085 (16) | 0.0003 (17) |
C9B | 0.045 (2) | 0.075 (3) | 0.026 (2) | −0.004 (2) | 0.0137 (17) | −0.003 (2) |
C10B | 0.041 (2) | 0.075 (3) | 0.031 (2) | 0.008 (2) | 0.0074 (18) | −0.017 (2) |
C11B | 0.033 (2) | 0.035 (2) | 0.046 (2) | 0.0025 (17) | −0.0016 (17) | −0.0077 (18) |
C12B | 0.041 (2) | 0.074 (3) | 0.028 (2) | −0.026 (2) | −0.0061 (18) | 0.019 (2) |
C13B | 0.043 (3) | 0.128 (5) | 0.040 (2) | −0.007 (3) | 0.014 (2) | −0.024 (3) |
C14B | 0.060 (3) | 0.062 (4) | 0.089 (4) | 0.010 (3) | −0.002 (3) | −0.029 (3) |
C15B | 0.064 (3) | 0.045 (3) | 0.061 (3) | −0.017 (2) | −0.003 (2) | 0.017 (2) |
C16B | 0.051 (2) | 0.058 (3) | 0.048 (2) | −0.021 (2) | 0.022 (2) | 0.000 (2) |
C17B | 0.036 (2) | 0.038 (2) | 0.054 (2) | −0.0012 (18) | 0.0033 (19) | −0.0009 (19) |
C18B | 0.0344 (19) | 0.0253 (19) | 0.0270 (18) | −0.0023 (15) | 0.0108 (16) | −0.0016 (15) |
C19B | 0.034 (2) | 0.035 (2) | 0.0332 (19) | −0.0016 (16) | 0.0135 (16) | −0.0015 (17) |
C20B | 0.047 (2) | 0.052 (3) | 0.029 (2) | −0.009 (2) | 0.0040 (17) | −0.0046 (19) |
C21B | 0.073 (3) | 0.046 (3) | 0.030 (2) | 0.000 (2) | 0.009 (2) | −0.0121 (19) |
C22B | 0.074 (3) | 0.052 (3) | 0.037 (2) | 0.028 (2) | 0.008 (2) | −0.009 (2) |
C23B | 0.045 (2) | 0.042 (2) | 0.029 (2) | 0.0102 (19) | 0.0061 (18) | −0.0021 (18) |
O24B | 0.0577 (17) | 0.064 (2) | 0.0372 (16) | 0.0259 (14) | 0.0034 (14) | −0.0132 (13) |
Geometric parameters (Å, º) top
C1A—C2A | 1.399 (4) | C2B—S3B | 1.765 (3) |
C1A—C8A | 1.404 (4) | C2B—S3B' | 1.792 (3) |
C1A—N7A | 1.407 (4) | S3B—C4B | 1.829 (3) |
C2A—C11A | 1.399 (4) | C4B—C12B | 1.507 (4) |
C2A—S3A | 1.778 (3) | C4B—C5B | 1.532 (4) |
S3A—C4A | 1.822 (3) | C4B—H4B | 1.0000 |
C4A—C12A | 1.516 (4) | C5B—C6B | 1.560 (4) |
C4A—C5A | 1.529 (4) | C5B—H5B1 | 0.9900 |
C4A—H4A | 1.0000 | C5B—H5B2 | 0.9900 |
C5A—C6A | 1.525 (4) | S3B'—C4B' | 1.827 (3) |
C5A—H5A1 | 0.9900 | C4B'—C5B' | 1.535 (4) |
C5A—H5A2 | 0.9900 | C4B'—C12B | 1.560 (6) |
C6A—N7A | 1.490 (4) | C4B'—H4B' | 1.0000 |
C6A—C18A | 1.509 (4) | C5B'—C6B | 1.525 (4) |
C6A—H6A | 1.0000 | C5B'—H5B3 | 0.9900 |
N7A—H7A | 0.79 (3) | C5B'—H5B4 | 0.9900 |
C8A—C9A | 1.389 (4) | C6B—N7B | 1.502 (4) |
C8A—H8A | 0.9500 | C6B—C18B | 1.509 (4) |
C9A—C10A | 1.368 (5) | C6B—H6B | 1.0000 |
C9A—H9A | 0.9500 | N7B—H7B | 0.79 (3) |
C10A—C11A | 1.385 (5) | C8B—C9B | 1.370 (4) |
C10A—H10A | 0.9500 | C8B—H8B | 0.9500 |
C11A—H11A | 0.9500 | C9B—C10B | 1.365 (5) |
C12A—C17A | 1.374 (4) | C9B—H9B | 0.9500 |
C12A—C13A | 1.401 (4) | C10B—C11B | 1.376 (4) |
C13A—C14A | 1.382 (4) | C10B—H10B | 0.9500 |
C13A—H13A | 0.9500 | C11B—H11B | 0.9500 |
C14A—C15A | 1.376 (5) | C12B—C17B | 1.376 (5) |
C14A—H14A | 0.9500 | C12B—C13B | 1.402 (6) |
C15A—C16A | 1.373 (4) | C13B—C14B | 1.363 (6) |
C15A—H15A | 0.9500 | C13B—H13B | 0.9500 |
C16A—C17A | 1.394 (4) | C14B—C15B | 1.344 (6) |
C16A—H16A | 0.9500 | C14B—H14B | 0.9500 |
C17A—H17A | 0.9500 | C15B—C16B | 1.369 (5) |
C18A—C19A | 1.386 (4) | C15B—H15B | 0.9500 |
C18A—C23A | 1.392 (4) | C16B—C17B | 1.369 (4) |
C19A—C20A | 1.383 (4) | C16B—H16B | 0.9500 |
C19A—H19A | 0.9500 | C17B—H17B | 0.9500 |
C20A—C21A | 1.381 (5) | C18B—C23B | 1.381 (4) |
C20A—H20A | 0.9500 | C18B—C19B | 1.393 (4) |
C21A—C22A | 1.371 (4) | C19B—C20B | 1.380 (4) |
C21A—H21A | 0.9500 | C19B—H19B | 0.9500 |
C22A—C23A | 1.392 (4) | C20B—C21B | 1.371 (5) |
C22A—H22A | 0.9500 | C20B—H20B | 0.9500 |
C23A—O24A | 1.377 (4) | C21B—C22B | 1.376 (4) |
O24A—H24A | 0.81 (3) | C21B—H21B | 0.9500 |
C1B—C2B | 1.389 (4) | C22B—C23B | 1.385 (4) |
C1B—C8B | 1.402 (4) | C22B—H22B | 0.9500 |
C1B—N7B | 1.424 (4) | C23B—O24B | 1.391 (4) |
C2B—C11B | 1.391 (4) | O24B—H24B | 0.77 (3) |
C2A—C1A—C8A | 118.4 (3) | C12B—C4B—S3B | 105.2 (2) |
C2A—C1A—N7A | 123.5 (3) | C5B—C4B—S3B | 113.3 (3) |
C8A—C1A—N7A | 118.1 (3) | C12B—C4B—H4B | 110.2 |
C1A—C2A—C11A | 119.7 (3) | C5B—C4B—H4B | 110.2 |
C1A—C2A—S3A | 126.2 (2) | S3B—C4B—H4B | 110.2 |
C11A—C2A—S3A | 114.1 (3) | C4B—C5B—C6B | 117.6 (3) |
C2A—S3A—C4A | 103.97 (14) | C4B—C5B—H5B1 | 107.9 |
C12A—C4A—C5A | 111.9 (2) | C6B—C5B—H5B1 | 107.9 |
C12A—C4A—S3A | 106.8 (2) | C4B—C5B—H5B2 | 107.9 |
C5A—C4A—S3A | 112.0 (2) | C6B—C5B—H5B2 | 107.9 |
C12A—C4A—H4A | 108.7 | H5B1—C5B—H5B2 | 107.2 |
C5A—C4A—H4A | 108.7 | C2B—S3B'—C4B' | 113.7 (4) |
S3A—C4A—H4A | 108.7 | C5B'—C4B'—C12B | 108.5 (5) |
C6A—C5A—C4A | 113.8 (2) | C5B'—C4B'—S3B' | 108.3 (6) |
C6A—C5A—H5A1 | 108.8 | C12B—C4B'—S3B' | 112.0 (4) |
C4A—C5A—H5A1 | 108.8 | C5B'—C4B'—H4B' | 109.3 |
C6A—C5A—H5A2 | 108.8 | C12B—C4B'—H4B' | 109.3 |
C4A—C5A—H5A2 | 108.8 | S3B'—C4B'—H4B' | 109.3 |
H5A1—C5A—H5A2 | 107.7 | C6B—C5B'—C4B' | 114.4 (5) |
N7A—C6A—C18A | 109.6 (2) | C6B—C5B'—H5B3 | 108.7 |
N7A—C6A—C5A | 110.5 (2) | C4B'—C5B'—H5B3 | 108.7 |
C18A—C6A—C5A | 112.0 (2) | C6B—C5B'—H5B4 | 108.7 |
N7A—C6A—H6A | 108.2 | C4B'—C5B'—H5B4 | 108.7 |
C18A—C6A—H6A | 108.2 | H5B3—C5B'—H5B4 | 107.6 |
C5A—C6A—H6A | 108.2 | N7B—C6B—C18B | 108.9 (3) |
C1A—N7A—C6A | 119.4 (3) | N7B—C6B—C5B' | 115.3 (4) |
C1A—N7A—H7A | 112 (2) | C18B—C6B—C5B' | 127.0 (5) |
C6A—N7A—H7A | 109 (3) | N7B—C6B—C5B | 112.7 (3) |
C9A—C8A—C1A | 121.0 (3) | C18B—C6B—C5B | 102.5 (3) |
C9A—C8A—H8A | 119.5 | N7B—C6B—H6B | 110.8 |
C1A—C8A—H8A | 119.5 | C18B—C6B—H6B | 110.8 |
C10A—C9A—C8A | 120.1 (3) | C5B'—C6B—H6B | 79.4 |
C10A—C9A—H9A | 119.9 | C5B—C6B—H6B | 110.8 |
C8A—C9A—H9A | 119.9 | C1B—N7B—C6B | 118.7 (3) |
C9A—C10A—C11A | 120.0 (3) | C1B—N7B—H7B | 110 (2) |
C9A—C10A—H10A | 120.0 | C6B—N7B—H7B | 103 (2) |
C11A—C10A—H10A | 120.0 | C9B—C8B—C1B | 121.6 (3) |
C10A—C11A—C2A | 120.7 (3) | C9B—C8B—H8B | 119.2 |
C10A—C11A—H11A | 119.6 | C1B—C8B—H8B | 119.2 |
C2A—C11A—H11A | 119.6 | C10B—C9B—C8B | 119.9 (3) |
C17A—C12A—C13A | 118.7 (3) | C10B—C9B—H9B | 120.0 |
C17A—C12A—C4A | 121.3 (3) | C8B—C9B—H9B | 120.0 |
C13A—C12A—C4A | 120.0 (3) | C9B—C10B—C11B | 119.9 (3) |
C14A—C13A—C12A | 120.4 (3) | C9B—C10B—H10B | 120.0 |
C14A—C13A—H13A | 119.8 | C11B—C10B—H10B | 120.0 |
C12A—C13A—H13A | 119.8 | C10B—C11B—C2B | 120.8 (3) |
C15A—C14A—C13A | 120.3 (3) | C10B—C11B—H11B | 119.6 |
C15A—C14A—H14A | 119.8 | C2B—C11B—H11B | 119.6 |
C13A—C14A—H14A | 119.8 | C17B—C12B—C13B | 117.3 (3) |
C14A—C15A—C16A | 119.7 (3) | C17B—C12B—C4B | 133.4 (4) |
C14A—C15A—H15A | 120.1 | C13B—C12B—C4B | 109.1 (4) |
C16A—C15A—H15A | 120.1 | C17B—C12B—C4B' | 101.9 (5) |
C15A—C16A—C17A | 120.4 (3) | C13B—C12B—C4B' | 140.6 (5) |
C15A—C16A—H16A | 119.8 | C14B—C13B—C12B | 120.2 (4) |
C17A—C16A—H16A | 119.8 | C14B—C13B—H13B | 119.9 |
C12A—C17A—C16A | 120.5 (3) | C12B—C13B—H13B | 119.9 |
C12A—C17A—H17A | 119.8 | C15B—C14B—C13B | 121.0 (4) |
C16A—C17A—H17A | 119.8 | C15B—C14B—H14B | 119.5 |
C19A—C18A—C23A | 117.8 (3) | C13B—C14B—H14B | 119.5 |
C19A—C18A—C6A | 120.4 (3) | C14B—C15B—C16B | 120.4 (4) |
C23A—C18A—C6A | 121.8 (3) | C14B—C15B—H15B | 119.8 |
C20A—C19A—C18A | 122.1 (3) | C16B—C15B—H15B | 119.8 |
C20A—C19A—H19A | 118.9 | C15B—C16B—C17B | 119.4 (4) |
C18A—C19A—H19A | 118.9 | C15B—C16B—H16B | 120.3 |
C21A—C20A—C19A | 118.7 (3) | C17B—C16B—H16B | 120.3 |
C21A—C20A—H20A | 120.7 | C16B—C17B—C12B | 121.6 (4) |
C19A—C20A—H20A | 120.7 | C16B—C17B—H17B | 119.2 |
C22A—C21A—C20A | 120.9 (3) | C12B—C17B—H17B | 119.2 |
C22A—C21A—H21A | 119.6 | C23B—C18B—C19B | 117.5 (3) |
C20A—C21A—H21A | 119.6 | C23B—C18B—C6B | 123.1 (3) |
C21A—C22A—C23A | 119.8 (3) | C19B—C18B—C6B | 119.3 (3) |
C21A—C22A—H22A | 120.1 | C20B—C19B—C18B | 122.1 (3) |
C23A—C22A—H22A | 120.1 | C20B—C19B—H19B | 119.0 |
O24A—C23A—C18A | 118.3 (3) | C18B—C19B—H19B | 119.0 |
O24A—C23A—C22A | 121.1 (3) | C21B—C20B—C19B | 119.1 (3) |
C18A—C23A—C22A | 120.6 (3) | C21B—C20B—H20B | 120.4 |
C23A—O24A—H24A | 115 (2) | C19B—C20B—H20B | 120.4 |
C2B—C1B—C8B | 117.8 (3) | C20B—C21B—C22B | 120.1 (3) |
C2B—C1B—N7B | 123.0 (3) | C20B—C21B—H21B | 119.9 |
C8B—C1B—N7B | 119.1 (3) | C22B—C21B—H21B | 119.9 |
C11B—C2B—C1B | 119.8 (2) | C21B—C22B—C23B | 120.3 (3) |
C11B—C2B—S3B | 112.5 (2) | C21B—C22B—H22B | 119.8 |
C1B—C2B—S3B | 127.7 (2) | C23B—C22B—H22B | 119.8 |
C11B—C2B—S3B' | 125.1 (3) | C18B—C23B—C22B | 120.8 (3) |
C1B—C2B—S3B' | 114.0 (3) | C18B—C23B—O24B | 122.2 (3) |
C2B—S3B—C4B | 98.72 (19) | C22B—C23B—O24B | 117.0 (3) |
C12B—C4B—C5B | 107.5 (3) | C23B—O24B—H24B | 112 (3) |
C8A—C1A—C2A—C11A | 0.6 (5) | C1B—C2B—S3B'—C4B' | −60.3 (5) |
N7A—C1A—C2A—C11A | 177.2 (3) | S3B—C2B—S3B'—C4B' | 88.7 (11) |
C8A—C1A—C2A—S3A | 179.7 (2) | C2B—S3B'—C4B'—C5B' | 8.5 (6) |
N7A—C1A—C2A—S3A | −3.7 (5) | C2B—S3B'—C4B'—C12B | −111.1 (5) |
C1A—C2A—S3A—C4A | 32.4 (3) | C12B—C4B'—C5B'—C6B | −168.2 (6) |
C11A—C2A—S3A—C4A | −148.5 (2) | S3B'—C4B'—C5B'—C6B | 70.0 (8) |
C2A—S3A—C4A—C12A | 157.3 (2) | C4B'—C5B'—C6B—N7B | −59.2 (8) |
C2A—S3A—C4A—C5A | −79.9 (2) | C4B'—C5B'—C6B—C18B | 84.5 (8) |
C12A—C4A—C5A—C6A | 165.2 (2) | C4B'—C5B'—C6B—C5B | 34.3 (5) |
S3A—C4A—C5A—C6A | 45.3 (3) | C4B—C5B—C6B—N7B | 64.8 (5) |
C4A—C5A—C6A—N7A | 44.9 (3) | C4B—C5B—C6B—C18B | −178.2 (4) |
C4A—C5A—C6A—C18A | 167.4 (3) | C4B—C5B—C6B—C5B' | −37.2 (7) |
C2A—C1A—N7A—C6A | 43.2 (4) | C2B—C1B—N7B—C6B | 69.7 (4) |
C8A—C1A—N7A—C6A | −140.1 (3) | C8B—C1B—N7B—C6B | −113.7 (3) |
C18A—C6A—N7A—C1A | 139.1 (3) | C18B—C6B—N7B—C1B | 169.0 (3) |
C5A—C6A—N7A—C1A | −96.9 (3) | C5B'—C6B—N7B—C1B | −41.0 (5) |
C2A—C1A—C8A—C9A | −2.4 (5) | C5B—C6B—N7B—C1B | −78.0 (4) |
N7A—C1A—C8A—C9A | −179.2 (3) | C2B—C1B—C8B—C9B | 2.4 (5) |
C1A—C8A—C9A—C10A | 1.8 (5) | N7B—C1B—C8B—C9B | −174.5 (3) |
C8A—C9A—C10A—C11A | 0.5 (5) | C1B—C8B—C9B—C10B | −2.8 (5) |
C9A—C10A—C11A—C2A | −2.2 (5) | C8B—C9B—C10B—C11B | 0.1 (5) |
C1A—C2A—C11A—C10A | 1.6 (5) | C9B—C10B—C11B—C2B | 2.8 (5) |
S3A—C2A—C11A—C10A | −177.5 (3) | C1B—C2B—C11B—C10B | −3.1 (5) |
C5A—C4A—C12A—C17A | 116.5 (3) | S3B—C2B—C11B—C10B | 176.3 (3) |
S3A—C4A—C12A—C17A | −120.5 (3) | S3B'—C2B—C11B—C10B | 164.3 (3) |
C5A—C4A—C12A—C13A | −61.5 (4) | C5B—C4B—C12B—C17B | 59.3 (5) |
S3A—C4A—C12A—C13A | 61.4 (3) | S3B—C4B—C12B—C17B | −61.8 (5) |
C17A—C12A—C13A—C14A | −2.0 (5) | C5B—C4B—C12B—C13B | −125.8 (4) |
C4A—C12A—C13A—C14A | 176.1 (3) | S3B—C4B—C12B—C13B | 113.2 (3) |
C12A—C13A—C14A—C15A | 0.6 (5) | C5B—C4B—C12B—C4B' | 42.0 (5) |
C13A—C14A—C15A—C16A | 0.6 (5) | S3B—C4B—C12B—C4B' | −79.0 (6) |
C14A—C15A—C16A—C17A | −0.5 (5) | C5B'—C4B'—C12B—C17B | 147.0 (6) |
C13A—C12A—C17A—C16A | 2.2 (5) | S3B'—C4B'—C12B—C17B | −93.6 (5) |
C4A—C12A—C17A—C16A | −175.9 (3) | C5B'—C4B'—C12B—C13B | −27.4 (9) |
C15A—C16A—C17A—C12A | −1.0 (5) | S3B'—C4B'—C12B—C13B | 92.1 (6) |
N7A—C6A—C18A—C19A | 69.4 (3) | C5B'—C4B'—C12B—C4B | −45.7 (6) |
C5A—C6A—C18A—C19A | −53.6 (4) | S3B'—C4B'—C12B—C4B | 73.7 (7) |
N7A—C6A—C18A—C23A | −109.6 (3) | C17B—C12B—C13B—C14B | 0.0 (5) |
C5A—C6A—C18A—C23A | 127.4 (3) | C4B—C12B—C13B—C14B | −175.8 (3) |
C23A—C18A—C19A—C20A | −1.6 (4) | C4B'—C12B—C13B—C14B | 173.9 (5) |
C6A—C18A—C19A—C20A | 179.4 (3) | C12B—C13B—C14B—C15B | −0.7 (6) |
C18A—C19A—C20A—C21A | −0.5 (5) | C13B—C14B—C15B—C16B | 0.4 (6) |
C19A—C20A—C21A—C22A | 1.0 (5) | C14B—C15B—C16B—C17B | 0.4 (6) |
C20A—C21A—C22A—C23A | 0.5 (5) | C15B—C16B—C17B—C12B | −1.0 (5) |
C19A—C18A—C23A—O24A | −177.7 (2) | C13B—C12B—C17B—C16B | 0.8 (5) |
C6A—C18A—C23A—O24A | 1.3 (4) | C4B—C12B—C17B—C16B | 175.4 (3) |
C19A—C18A—C23A—C22A | 3.2 (4) | C4B'—C12B—C17B—C16B | −175.2 (4) |
C6A—C18A—C23A—C22A | −177.8 (3) | N7B—C6B—C18B—C23B | 41.0 (4) |
C21A—C22A—C23A—O24A | 178.2 (3) | C5B'—C6B—C18B—C23B | −104.5 (5) |
C21A—C22A—C23A—C18A | −2.7 (4) | C5B—C6B—C18B—C23B | −78.6 (4) |
C8B—C1B—C2B—C11B | 0.6 (5) | N7B—C6B—C18B—C19B | −142.7 (3) |
N7B—C1B—C2B—C11B | 177.3 (3) | C5B'—C6B—C18B—C19B | 71.8 (5) |
C8B—C1B—C2B—S3B | −178.8 (3) | C5B—C6B—C18B—C19B | 97.7 (3) |
N7B—C1B—C2B—S3B | −2.0 (5) | C23B—C18B—C19B—C20B | −0.1 (5) |
C8B—C1B—C2B—S3B' | −168.2 (3) | C6B—C18B—C19B—C20B | −176.5 (3) |
N7B—C1B—C2B—S3B' | 8.6 (5) | C18B—C19B—C20B—C21B | −0.8 (5) |
C11B—C2B—S3B—C4B | 124.7 (3) | C19B—C20B—C21B—C22B | 0.8 (5) |
C1B—C2B—S3B—C4B | −56.0 (4) | C20B—C21B—C22B—C23B | 0.0 (6) |
S3B'—C2B—S3B—C4B | −92.4 (10) | C19B—C18B—C23B—C22B | 0.9 (5) |
C2B—S3B—C4B—C12B | −166.5 (3) | C6B—C18B—C23B—C22B | 177.2 (3) |
C2B—S3B—C4B—C5B | 76.3 (3) | C19B—C18B—C23B—O24B | −178.3 (3) |
C12B—C4B—C5B—C6B | 169.3 (4) | C6B—C18B—C23B—O24B | −2.0 (5) |
S3B—C4B—C5B—C6B | −74.9 (5) | C21B—C22B—C23B—C18B | −0.9 (5) |
C11B—C2B—S3B'—C4B' | 131.7 (4) | C21B—C22B—C23B—O24B | 178.3 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O24A—H24A···O24Bi | 0.81 (3) | 2.07 (3) | 2.871 (3) | 168 (3) |
O24B—H24B···N7B | 0.77 (3) | 2.06 (3) | 2.706 (4) | 141 (3) |
C6A—H6A···O24A | 1.00 | 2.36 | 2.841 (4) | 108 |
Symmetry code: (i) −x, −y+1, −z. |