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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802004580/cv6096sup1.cif
Contains datablocks Global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802004580/cv6096Isup2.hkl
Contains datablock I

CCDC reference: 183800

Key indicators

  • Single-crystal X-ray study
  • T = 170 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.068
  • wR factor = 0.148
  • Data-to-parameter ratio = 17.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_420 Alert C D-H Without Acceptor N7A - H7A ? PLAT_420 Alert C D-H Without Acceptor N7B - H7B ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

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
C21H19NOSDx = 1.291 Mg m3
Mr = 333.43Melting point: 363 K K
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
a = 10.3404 (1) ÅCell parameters from 12187 reflections
b = 36.9797 (7) Åθ = 1.0–27.5°
c = 9.4929 (1) ŵ = 0.20 mm1
β = 108.993 (1)°T = 170 K
V = 3432.32 (8) Å3Block, colourless
Z = 80.15 × 0.15 × 0.15 mm
F(000) = 1408
Data collection top
Nonius KappaCCD
diffractometer
7825 independent reflections
Radiation source: fine-focus sealed tube3496 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.088
ω and φ scansθmax = 27.6°, θmin = 3.9°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 1313
Tmin = 0.97, Tmax = 0.97k = 4747
23647 measured reflectionsl = 1211
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H 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 parametersΔρmax = 0.45 e Å3
14 restraintsΔρmin = 0.53 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C1A0.4879 (3)0.38069 (9)0.1634 (3)0.0326 (8)
C2A0.3908 (3)0.35310 (9)0.1420 (3)0.0341 (8)
S3A0.28795 (9)0.33514 (2)0.03227 (9)0.0394 (3)
C4A0.3962 (3)0.33867 (8)0.1496 (3)0.0297 (8)
H4A0.49190.33210.08890.036*
C5A0.3964 (3)0.37692 (8)0.2106 (3)0.0309 (8)
H5A10.47200.37900.25280.037*
H5A20.30950.38090.29270.037*
C6A0.4127 (3)0.40652 (8)0.0943 (3)0.0284 (8)
H6A0.32480.40860.07220.034*
N7A0.5229 (3)0.39685 (8)0.0465 (3)0.0336 (7)
H7A0.572 (3)0.4136 (9)0.074 (4)0.044 (6)*
C8A0.5594 (3)0.39159 (9)0.3098 (3)0.0405 (9)
H8A0.62820.40960.32660.049*
C9A0.5311 (4)0.37639 (12)0.4303 (4)0.0502 (10)
H9A0.57860.38460.52840.060*
C10A0.4351 (4)0.34965 (11)0.4081 (4)0.0522 (10)
H10A0.41550.33940.49070.063*
C11A0.3665 (4)0.33749 (10)0.2653 (4)0.0458 (9)
H11A0.30230.31830.25090.055*
C12A0.3437 (3)0.31110 (9)0.2733 (3)0.0305 (8)
C13A0.2100 (3)0.31377 (9)0.3726 (3)0.0408 (9)
H13A0.15060.33200.35830.049*
C14A0.1638 (4)0.29012 (10)0.4911 (4)0.0463 (9)
H14A0.07330.29230.55840.056*
C15A0.2485 (4)0.26344 (10)0.5120 (4)0.0500 (10)
H15A0.21680.24740.59420.060*
C16A0.3789 (4)0.26016 (10)0.4137 (4)0.0509 (10)
H16A0.43730.24160.42760.061*
C17A0.4262 (4)0.28386 (9)0.2936 (3)0.0408 (9)
H17A0.51620.28110.22530.049*
C18A0.4436 (3)0.44280 (9)0.1488 (3)0.0302 (8)
C19A0.5520 (3)0.44664 (9)0.2033 (3)0.0384 (9)
H19A0.60690.42610.20480.046*
C20A0.5828 (4)0.47933 (10)0.2556 (3)0.0443 (9)
H20A0.65810.48140.29170.053*
C21A0.5019 (4)0.50898 (10)0.2543 (3)0.0445 (9)
H21A0.52100.53150.29140.053*
C22A0.3945 (3)0.50632 (9)0.2001 (3)0.0381 (8)
H22A0.33920.52690.20050.046*
C23A0.3668 (3)0.47345 (9)0.1444 (3)0.0313 (8)
O24A0.2619 (2)0.47023 (6)0.0857 (2)0.0407 (6)
H24A0.230 (3)0.4894 (9)0.070 (3)0.044 (6)*
C1B0.0430 (3)0.40185 (9)0.2248 (3)0.0306 (8)
C2B0.1259 (3)0.37147 (8)0.2642 (3)0.0308 (8)
S3B0.2192 (3)0.35023 (7)0.1613 (3)0.0374 (6)0.663 (4)
C4B0.0783 (4)0.34177 (12)0.0111 (4)0.0380 (14)0.663 (4)
H4B0.00080.33070.01180.046*0.663 (4)
C5B0.0321 (5)0.37565 (11)0.1072 (5)0.0365 (13)0.663 (4)
H5B10.02220.36780.20890.044*0.663 (4)
H5B20.11480.38790.11440.044*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'0.15820.37210.11370.046*0.337 (4)
C5B'0.0246 (8)0.36410 (14)0.0683 (12)0.0365 (13)0.337 (4)
H5B30.08240.35540.16730.044*0.337 (4)
H5B40.05130.35050.00790.044*0.337 (4)
C6B0.0541 (3)0.40413 (8)0.0550 (3)0.0368 (8)
H6B0.14080.39310.04990.044*
N7B0.0248 (3)0.42149 (8)0.0907 (3)0.0355 (7)
H7B0.016 (3)0.4394 (9)0.091 (3)0.044 (6)*
C8B0.0195 (3)0.41451 (9)0.3261 (3)0.0398 (9)
H8B0.07940.43470.29970.048*
C9B0.0037 (3)0.39847 (11)0.4622 (4)0.0482 (10)
H9B0.03670.40820.53070.058*
C10B0.0848 (4)0.36852 (12)0.4993 (4)0.0499 (10)
H10B0.10090.35730.59360.060*
C11B0.1435 (3)0.35454 (9)0.4000 (4)0.0415 (9)
H11B0.19650.33310.42460.050*
C12B0.1347 (4)0.31558 (12)0.0980 (3)0.0517 (11)
C13B0.0672 (4)0.28232 (17)0.1079 (4)0.0703 (15)
H13B0.00610.27990.06880.084*
C14B0.1063 (5)0.25342 (14)0.1735 (5)0.0769 (14)
H14B0.06040.23100.17870.092*
C15B0.2088 (5)0.25622 (12)0.2309 (4)0.0622 (12)
H15B0.23420.23580.27680.075*
C16B0.2767 (4)0.28828 (12)0.2237 (4)0.0513 (10)
H16B0.34880.29030.26490.062*
C17B0.2400 (3)0.31747 (10)0.1566 (4)0.0451 (9)
H17B0.28840.33960.15030.054*
C18B0.0837 (3)0.43223 (8)0.1766 (3)0.0287 (8)
C19B0.2088 (3)0.43147 (9)0.2911 (3)0.0336 (8)
H19B0.27520.41410.28750.040*
C20B0.2393 (4)0.45521 (10)0.4096 (3)0.0451 (9)
H20B0.32500.45390.48700.054*
C21B0.1444 (4)0.48066 (10)0.4143 (4)0.0515 (10)
H21B0.16460.49740.49460.062*
C22B0.0198 (4)0.48208 (10)0.3029 (4)0.0569 (11)
H22B0.04560.49980.30660.068*
C23B0.0106 (3)0.45784 (10)0.1853 (3)0.0403 (9)
O24B0.1399 (3)0.46032 (8)0.0790 (3)0.0557 (8)
H24B0.146 (3)0.4485 (9)0.010 (3)0.044 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.039 (2)0.032 (2)0.0296 (19)0.0133 (17)0.0151 (16)0.0081 (16)
C2A0.044 (2)0.030 (2)0.0334 (19)0.0110 (17)0.0185 (16)0.0051 (16)
S3A0.0553 (6)0.0288 (5)0.0403 (5)0.0049 (4)0.0240 (4)0.0016 (4)
C4A0.0367 (19)0.0235 (19)0.0298 (18)0.0002 (15)0.0120 (15)0.0007 (15)
C5A0.0359 (19)0.028 (2)0.0281 (18)0.0025 (15)0.0097 (15)0.0002 (15)
C6A0.0331 (18)0.026 (2)0.0237 (17)0.0009 (15)0.0061 (15)0.0028 (15)
N7A0.0449 (19)0.0266 (19)0.0276 (16)0.0008 (14)0.0094 (14)0.0001 (14)
C8A0.041 (2)0.048 (2)0.029 (2)0.0144 (18)0.0071 (17)0.0041 (18)
C9A0.054 (3)0.067 (3)0.028 (2)0.024 (2)0.0112 (19)0.006 (2)
C10A0.071 (3)0.058 (3)0.036 (2)0.019 (2)0.028 (2)0.017 (2)
C11A0.066 (3)0.041 (2)0.039 (2)0.0050 (19)0.029 (2)0.0096 (18)
C12A0.037 (2)0.024 (2)0.0307 (18)0.0036 (16)0.0114 (16)0.0028 (15)
C13A0.042 (2)0.033 (2)0.045 (2)0.0014 (18)0.0118 (19)0.0035 (18)
C14A0.048 (2)0.035 (2)0.047 (2)0.0058 (19)0.0027 (18)0.0059 (19)
C15A0.070 (3)0.028 (2)0.046 (2)0.006 (2)0.010 (2)0.0072 (18)
C16A0.060 (3)0.034 (2)0.050 (2)0.0086 (19)0.007 (2)0.009 (2)
C17A0.048 (2)0.032 (2)0.036 (2)0.0079 (18)0.0062 (17)0.0015 (17)
C18A0.037 (2)0.029 (2)0.0231 (17)0.0082 (16)0.0075 (15)0.0012 (15)
C19A0.048 (2)0.030 (2)0.035 (2)0.0045 (17)0.0100 (17)0.0027 (16)
C20A0.053 (2)0.035 (2)0.051 (2)0.0118 (19)0.0245 (19)0.0014 (19)
C21A0.062 (3)0.031 (2)0.040 (2)0.013 (2)0.0169 (19)0.0011 (17)
C22A0.048 (2)0.024 (2)0.038 (2)0.0034 (17)0.0089 (17)0.0004 (16)
C23A0.037 (2)0.030 (2)0.0245 (18)0.0020 (16)0.0059 (15)0.0024 (15)
O24A0.0484 (16)0.0297 (16)0.0459 (14)0.0021 (12)0.0180 (12)0.0041 (12)
C1B0.0331 (19)0.031 (2)0.0252 (18)0.0018 (16)0.0058 (15)0.0039 (16)
C2B0.0276 (19)0.032 (2)0.0286 (19)0.0032 (16)0.0038 (15)0.0027 (16)
S3B0.0410 (7)0.0328 (16)0.0319 (7)0.0153 (11)0.0029 (5)0.0008 (10)
C4B0.026 (3)0.062 (4)0.034 (3)0.007 (3)0.022 (2)0.001 (3)
C5B0.060 (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)
C6B0.040 (2)0.034 (2)0.032 (2)0.0054 (17)0.0070 (16)0.0009 (17)
N7B0.0492 (19)0.0273 (19)0.0275 (16)0.0037 (14)0.0088 (14)0.0010 (14)
C8B0.043 (2)0.046 (2)0.0284 (19)0.0074 (17)0.0085 (16)0.0003 (17)
C9B0.045 (2)0.075 (3)0.026 (2)0.004 (2)0.0137 (17)0.003 (2)
C10B0.041 (2)0.075 (3)0.031 (2)0.008 (2)0.0074 (18)0.017 (2)
C11B0.033 (2)0.035 (2)0.046 (2)0.0025 (17)0.0016 (17)0.0077 (18)
C12B0.041 (2)0.074 (3)0.028 (2)0.026 (2)0.0061 (18)0.019 (2)
C13B0.043 (3)0.128 (5)0.040 (2)0.007 (3)0.014 (2)0.024 (3)
C14B0.060 (3)0.062 (4)0.089 (4)0.010 (3)0.002 (3)0.029 (3)
C15B0.064 (3)0.045 (3)0.061 (3)0.017 (2)0.003 (2)0.017 (2)
C16B0.051 (2)0.058 (3)0.048 (2)0.021 (2)0.022 (2)0.000 (2)
C17B0.036 (2)0.038 (2)0.054 (2)0.0012 (18)0.0033 (19)0.0009 (19)
C18B0.0344 (19)0.0253 (19)0.0270 (18)0.0023 (15)0.0108 (16)0.0016 (15)
C19B0.034 (2)0.035 (2)0.0332 (19)0.0016 (16)0.0135 (16)0.0015 (17)
C20B0.047 (2)0.052 (3)0.029 (2)0.009 (2)0.0040 (17)0.0046 (19)
C21B0.073 (3)0.046 (3)0.030 (2)0.000 (2)0.009 (2)0.0121 (19)
C22B0.074 (3)0.052 (3)0.037 (2)0.028 (2)0.008 (2)0.009 (2)
C23B0.045 (2)0.042 (2)0.029 (2)0.0102 (19)0.0061 (18)0.0021 (18)
O24B0.0577 (17)0.064 (2)0.0372 (16)0.0259 (14)0.0034 (14)0.0132 (13)
Geometric parameters (Å, º) top
C1A—C2A1.399 (4)C2B—S3B1.765 (3)
C1A—C8A1.404 (4)C2B—S3B'1.792 (3)
C1A—N7A1.407 (4)S3B—C4B1.829 (3)
C2A—C11A1.399 (4)C4B—C12B1.507 (4)
C2A—S3A1.778 (3)C4B—C5B1.532 (4)
S3A—C4A1.822 (3)C4B—H4B1.0000
C4A—C12A1.516 (4)C5B—C6B1.560 (4)
C4A—C5A1.529 (4)C5B—H5B10.9900
C4A—H4A1.0000C5B—H5B20.9900
C5A—C6A1.525 (4)S3B'—C4B'1.827 (3)
C5A—H5A10.9900C4B'—C5B'1.535 (4)
C5A—H5A20.9900C4B'—C12B1.560 (6)
C6A—N7A1.490 (4)C4B'—H4B'1.0000
C6A—C18A1.509 (4)C5B'—C6B1.525 (4)
C6A—H6A1.0000C5B'—H5B30.9900
N7A—H7A0.79 (3)C5B'—H5B40.9900
C8A—C9A1.389 (4)C6B—N7B1.502 (4)
C8A—H8A0.9500C6B—C18B1.509 (4)
C9A—C10A1.368 (5)C6B—H6B1.0000
C9A—H9A0.9500N7B—H7B0.79 (3)
C10A—C11A1.385 (5)C8B—C9B1.370 (4)
C10A—H10A0.9500C8B—H8B0.9500
C11A—H11A0.9500C9B—C10B1.365 (5)
C12A—C17A1.374 (4)C9B—H9B0.9500
C12A—C13A1.401 (4)C10B—C11B1.376 (4)
C13A—C14A1.382 (4)C10B—H10B0.9500
C13A—H13A0.9500C11B—H11B0.9500
C14A—C15A1.376 (5)C12B—C17B1.376 (5)
C14A—H14A0.9500C12B—C13B1.402 (6)
C15A—C16A1.373 (4)C13B—C14B1.363 (6)
C15A—H15A0.9500C13B—H13B0.9500
C16A—C17A1.394 (4)C14B—C15B1.344 (6)
C16A—H16A0.9500C14B—H14B0.9500
C17A—H17A0.9500C15B—C16B1.369 (5)
C18A—C19A1.386 (4)C15B—H15B0.9500
C18A—C23A1.392 (4)C16B—C17B1.369 (4)
C19A—C20A1.383 (4)C16B—H16B0.9500
C19A—H19A0.9500C17B—H17B0.9500
C20A—C21A1.381 (5)C18B—C23B1.381 (4)
C20A—H20A0.9500C18B—C19B1.393 (4)
C21A—C22A1.371 (4)C19B—C20B1.380 (4)
C21A—H21A0.9500C19B—H19B0.9500
C22A—C23A1.392 (4)C20B—C21B1.371 (5)
C22A—H22A0.9500C20B—H20B0.9500
C23A—O24A1.377 (4)C21B—C22B1.376 (4)
O24A—H24A0.81 (3)C21B—H21B0.9500
C1B—C2B1.389 (4)C22B—C23B1.385 (4)
C1B—C8B1.402 (4)C22B—H22B0.9500
C1B—N7B1.424 (4)C23B—O24B1.391 (4)
C2B—C11B1.391 (4)O24B—H24B0.77 (3)
C2A—C1A—C8A118.4 (3)C12B—C4B—S3B105.2 (2)
C2A—C1A—N7A123.5 (3)C5B—C4B—S3B113.3 (3)
C8A—C1A—N7A118.1 (3)C12B—C4B—H4B110.2
C1A—C2A—C11A119.7 (3)C5B—C4B—H4B110.2
C1A—C2A—S3A126.2 (2)S3B—C4B—H4B110.2
C11A—C2A—S3A114.1 (3)C4B—C5B—C6B117.6 (3)
C2A—S3A—C4A103.97 (14)C4B—C5B—H5B1107.9
C12A—C4A—C5A111.9 (2)C6B—C5B—H5B1107.9
C12A—C4A—S3A106.8 (2)C4B—C5B—H5B2107.9
C5A—C4A—S3A112.0 (2)C6B—C5B—H5B2107.9
C12A—C4A—H4A108.7H5B1—C5B—H5B2107.2
C5A—C4A—H4A108.7C2B—S3B'—C4B'113.7 (4)
S3A—C4A—H4A108.7C5B'—C4B'—C12B108.5 (5)
C6A—C5A—C4A113.8 (2)C5B'—C4B'—S3B'108.3 (6)
C6A—C5A—H5A1108.8C12B—C4B'—S3B'112.0 (4)
C4A—C5A—H5A1108.8C5B'—C4B'—H4B'109.3
C6A—C5A—H5A2108.8C12B—C4B'—H4B'109.3
C4A—C5A—H5A2108.8S3B'—C4B'—H4B'109.3
H5A1—C5A—H5A2107.7C6B—C5B'—C4B'114.4 (5)
N7A—C6A—C18A109.6 (2)C6B—C5B'—H5B3108.7
N7A—C6A—C5A110.5 (2)C4B'—C5B'—H5B3108.7
C18A—C6A—C5A112.0 (2)C6B—C5B'—H5B4108.7
N7A—C6A—H6A108.2C4B'—C5B'—H5B4108.7
C18A—C6A—H6A108.2H5B3—C5B'—H5B4107.6
C5A—C6A—H6A108.2N7B—C6B—C18B108.9 (3)
C1A—N7A—C6A119.4 (3)N7B—C6B—C5B'115.3 (4)
C1A—N7A—H7A112 (2)C18B—C6B—C5B'127.0 (5)
C6A—N7A—H7A109 (3)N7B—C6B—C5B112.7 (3)
C9A—C8A—C1A121.0 (3)C18B—C6B—C5B102.5 (3)
C9A—C8A—H8A119.5N7B—C6B—H6B110.8
C1A—C8A—H8A119.5C18B—C6B—H6B110.8
C10A—C9A—C8A120.1 (3)C5B'—C6B—H6B79.4
C10A—C9A—H9A119.9C5B—C6B—H6B110.8
C8A—C9A—H9A119.9C1B—N7B—C6B118.7 (3)
C9A—C10A—C11A120.0 (3)C1B—N7B—H7B110 (2)
C9A—C10A—H10A120.0C6B—N7B—H7B103 (2)
C11A—C10A—H10A120.0C9B—C8B—C1B121.6 (3)
C10A—C11A—C2A120.7 (3)C9B—C8B—H8B119.2
C10A—C11A—H11A119.6C1B—C8B—H8B119.2
C2A—C11A—H11A119.6C10B—C9B—C8B119.9 (3)
C17A—C12A—C13A118.7 (3)C10B—C9B—H9B120.0
C17A—C12A—C4A121.3 (3)C8B—C9B—H9B120.0
C13A—C12A—C4A120.0 (3)C9B—C10B—C11B119.9 (3)
C14A—C13A—C12A120.4 (3)C9B—C10B—H10B120.0
C14A—C13A—H13A119.8C11B—C10B—H10B120.0
C12A—C13A—H13A119.8C10B—C11B—C2B120.8 (3)
C15A—C14A—C13A120.3 (3)C10B—C11B—H11B119.6
C15A—C14A—H14A119.8C2B—C11B—H11B119.6
C13A—C14A—H14A119.8C17B—C12B—C13B117.3 (3)
C14A—C15A—C16A119.7 (3)C17B—C12B—C4B133.4 (4)
C14A—C15A—H15A120.1C13B—C12B—C4B109.1 (4)
C16A—C15A—H15A120.1C17B—C12B—C4B'101.9 (5)
C15A—C16A—C17A120.4 (3)C13B—C12B—C4B'140.6 (5)
C15A—C16A—H16A119.8C14B—C13B—C12B120.2 (4)
C17A—C16A—H16A119.8C14B—C13B—H13B119.9
C12A—C17A—C16A120.5 (3)C12B—C13B—H13B119.9
C12A—C17A—H17A119.8C15B—C14B—C13B121.0 (4)
C16A—C17A—H17A119.8C15B—C14B—H14B119.5
C19A—C18A—C23A117.8 (3)C13B—C14B—H14B119.5
C19A—C18A—C6A120.4 (3)C14B—C15B—C16B120.4 (4)
C23A—C18A—C6A121.8 (3)C14B—C15B—H15B119.8
C20A—C19A—C18A122.1 (3)C16B—C15B—H15B119.8
C20A—C19A—H19A118.9C15B—C16B—C17B119.4 (4)
C18A—C19A—H19A118.9C15B—C16B—H16B120.3
C21A—C20A—C19A118.7 (3)C17B—C16B—H16B120.3
C21A—C20A—H20A120.7C16B—C17B—C12B121.6 (4)
C19A—C20A—H20A120.7C16B—C17B—H17B119.2
C22A—C21A—C20A120.9 (3)C12B—C17B—H17B119.2
C22A—C21A—H21A119.6C23B—C18B—C19B117.5 (3)
C20A—C21A—H21A119.6C23B—C18B—C6B123.1 (3)
C21A—C22A—C23A119.8 (3)C19B—C18B—C6B119.3 (3)
C21A—C22A—H22A120.1C20B—C19B—C18B122.1 (3)
C23A—C22A—H22A120.1C20B—C19B—H19B119.0
O24A—C23A—C18A118.3 (3)C18B—C19B—H19B119.0
O24A—C23A—C22A121.1 (3)C21B—C20B—C19B119.1 (3)
C18A—C23A—C22A120.6 (3)C21B—C20B—H20B120.4
C23A—O24A—H24A115 (2)C19B—C20B—H20B120.4
C2B—C1B—C8B117.8 (3)C20B—C21B—C22B120.1 (3)
C2B—C1B—N7B123.0 (3)C20B—C21B—H21B119.9
C8B—C1B—N7B119.1 (3)C22B—C21B—H21B119.9
C11B—C2B—C1B119.8 (2)C21B—C22B—C23B120.3 (3)
C11B—C2B—S3B112.5 (2)C21B—C22B—H22B119.8
C1B—C2B—S3B127.7 (2)C23B—C22B—H22B119.8
C11B—C2B—S3B'125.1 (3)C18B—C23B—C22B120.8 (3)
C1B—C2B—S3B'114.0 (3)C18B—C23B—O24B122.2 (3)
C2B—S3B—C4B98.72 (19)C22B—C23B—O24B117.0 (3)
C12B—C4B—C5B107.5 (3)C23B—O24B—H24B112 (3)
C8A—C1A—C2A—C11A0.6 (5)C1B—C2B—S3B'—C4B'60.3 (5)
N7A—C1A—C2A—C11A177.2 (3)S3B—C2B—S3B'—C4B'88.7 (11)
C8A—C1A—C2A—S3A179.7 (2)C2B—S3B'—C4B'—C5B'8.5 (6)
N7A—C1A—C2A—S3A3.7 (5)C2B—S3B'—C4B'—C12B111.1 (5)
C1A—C2A—S3A—C4A32.4 (3)C12B—C4B'—C5B'—C6B168.2 (6)
C11A—C2A—S3A—C4A148.5 (2)S3B'—C4B'—C5B'—C6B70.0 (8)
C2A—S3A—C4A—C12A157.3 (2)C4B'—C5B'—C6B—N7B59.2 (8)
C2A—S3A—C4A—C5A79.9 (2)C4B'—C5B'—C6B—C18B84.5 (8)
C12A—C4A—C5A—C6A165.2 (2)C4B'—C5B'—C6B—C5B34.3 (5)
S3A—C4A—C5A—C6A45.3 (3)C4B—C5B—C6B—N7B64.8 (5)
C4A—C5A—C6A—N7A44.9 (3)C4B—C5B—C6B—C18B178.2 (4)
C4A—C5A—C6A—C18A167.4 (3)C4B—C5B—C6B—C5B'37.2 (7)
C2A—C1A—N7A—C6A43.2 (4)C2B—C1B—N7B—C6B69.7 (4)
C8A—C1A—N7A—C6A140.1 (3)C8B—C1B—N7B—C6B113.7 (3)
C18A—C6A—N7A—C1A139.1 (3)C18B—C6B—N7B—C1B169.0 (3)
C5A—C6A—N7A—C1A96.9 (3)C5B'—C6B—N7B—C1B41.0 (5)
C2A—C1A—C8A—C9A2.4 (5)C5B—C6B—N7B—C1B78.0 (4)
N7A—C1A—C8A—C9A179.2 (3)C2B—C1B—C8B—C9B2.4 (5)
C1A—C8A—C9A—C10A1.8 (5)N7B—C1B—C8B—C9B174.5 (3)
C8A—C9A—C10A—C11A0.5 (5)C1B—C8B—C9B—C10B2.8 (5)
C9A—C10A—C11A—C2A2.2 (5)C8B—C9B—C10B—C11B0.1 (5)
C1A—C2A—C11A—C10A1.6 (5)C9B—C10B—C11B—C2B2.8 (5)
S3A—C2A—C11A—C10A177.5 (3)C1B—C2B—C11B—C10B3.1 (5)
C5A—C4A—C12A—C17A116.5 (3)S3B—C2B—C11B—C10B176.3 (3)
S3A—C4A—C12A—C17A120.5 (3)S3B'—C2B—C11B—C10B164.3 (3)
C5A—C4A—C12A—C13A61.5 (4)C5B—C4B—C12B—C17B59.3 (5)
S3A—C4A—C12A—C13A61.4 (3)S3B—C4B—C12B—C17B61.8 (5)
C17A—C12A—C13A—C14A2.0 (5)C5B—C4B—C12B—C13B125.8 (4)
C4A—C12A—C13A—C14A176.1 (3)S3B—C4B—C12B—C13B113.2 (3)
C12A—C13A—C14A—C15A0.6 (5)C5B—C4B—C12B—C4B'42.0 (5)
C13A—C14A—C15A—C16A0.6 (5)S3B—C4B—C12B—C4B'79.0 (6)
C14A—C15A—C16A—C17A0.5 (5)C5B'—C4B'—C12B—C17B147.0 (6)
C13A—C12A—C17A—C16A2.2 (5)S3B'—C4B'—C12B—C17B93.6 (5)
C4A—C12A—C17A—C16A175.9 (3)C5B'—C4B'—C12B—C13B27.4 (9)
C15A—C16A—C17A—C12A1.0 (5)S3B'—C4B'—C12B—C13B92.1 (6)
N7A—C6A—C18A—C19A69.4 (3)C5B'—C4B'—C12B—C4B45.7 (6)
C5A—C6A—C18A—C19A53.6 (4)S3B'—C4B'—C12B—C4B73.7 (7)
N7A—C6A—C18A—C23A109.6 (3)C17B—C12B—C13B—C14B0.0 (5)
C5A—C6A—C18A—C23A127.4 (3)C4B—C12B—C13B—C14B175.8 (3)
C23A—C18A—C19A—C20A1.6 (4)C4B'—C12B—C13B—C14B173.9 (5)
C6A—C18A—C19A—C20A179.4 (3)C12B—C13B—C14B—C15B0.7 (6)
C18A—C19A—C20A—C21A0.5 (5)C13B—C14B—C15B—C16B0.4 (6)
C19A—C20A—C21A—C22A1.0 (5)C14B—C15B—C16B—C17B0.4 (6)
C20A—C21A—C22A—C23A0.5 (5)C15B—C16B—C17B—C12B1.0 (5)
C19A—C18A—C23A—O24A177.7 (2)C13B—C12B—C17B—C16B0.8 (5)
C6A—C18A—C23A—O24A1.3 (4)C4B—C12B—C17B—C16B175.4 (3)
C19A—C18A—C23A—C22A3.2 (4)C4B'—C12B—C17B—C16B175.2 (4)
C6A—C18A—C23A—C22A177.8 (3)N7B—C6B—C18B—C23B41.0 (4)
C21A—C22A—C23A—O24A178.2 (3)C5B'—C6B—C18B—C23B104.5 (5)
C21A—C22A—C23A—C18A2.7 (4)C5B—C6B—C18B—C23B78.6 (4)
C8B—C1B—C2B—C11B0.6 (5)N7B—C6B—C18B—C19B142.7 (3)
N7B—C1B—C2B—C11B177.3 (3)C5B'—C6B—C18B—C19B71.8 (5)
C8B—C1B—C2B—S3B178.8 (3)C5B—C6B—C18B—C19B97.7 (3)
N7B—C1B—C2B—S3B2.0 (5)C23B—C18B—C19B—C20B0.1 (5)
C8B—C1B—C2B—S3B'168.2 (3)C6B—C18B—C19B—C20B176.5 (3)
N7B—C1B—C2B—S3B'8.6 (5)C18B—C19B—C20B—C21B0.8 (5)
C11B—C2B—S3B—C4B124.7 (3)C19B—C20B—C21B—C22B0.8 (5)
C1B—C2B—S3B—C4B56.0 (4)C20B—C21B—C22B—C23B0.0 (6)
S3B'—C2B—S3B—C4B92.4 (10)C19B—C18B—C23B—C22B0.9 (5)
C2B—S3B—C4B—C12B166.5 (3)C6B—C18B—C23B—C22B177.2 (3)
C2B—S3B—C4B—C5B76.3 (3)C19B—C18B—C23B—O24B178.3 (3)
C12B—C4B—C5B—C6B169.3 (4)C6B—C18B—C23B—O24B2.0 (5)
S3B—C4B—C5B—C6B74.9 (5)C21B—C22B—C23B—C18B0.9 (5)
C11B—C2B—S3B'—C4B'131.7 (4)C21B—C22B—C23B—O24B178.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O24A—H24A···O24Bi0.81 (3)2.07 (3)2.871 (3)168 (3)
O24B—H24B···N7B0.77 (3)2.06 (3)2.706 (4)141 (3)
C6A—H6A···O24A1.002.362.841 (4)108
Symmetry code: (i) x, y+1, z.
 

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