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The title compound, C24H20N2O3S, crystallizes with two independent mol­ecules in the asymmetric unit, related by a non-crystallographic twofold rotation axis. The two mol­ecules differ in the relative orientations of the phenyl­sulfonyl group and the indole ring system. In both mol­ecules, the seven-membered ring adopts a distorted boat conformation. The mol­ecular packing is stabilized by C—H...π and C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805020842/rz6097sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805020842/rz6097Isup2.hkl
Contains datablock I

CCDC reference: 282583

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.051
  • wR factor = 0.123
  • Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C20A - C21A .. 7.76 su
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT230_ALERT_2_C Hirshfeld Test Diff for C20B - C21B .. 6.87 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C11B PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C13B PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9B PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C9B -C14B 1.37 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT480_ALERT_4_C Long H...A H-Bond Reported H24D .. CG1 .. 2.90 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.29 From the CIF: _reflns_number_total 8896 Count of symmetry unique reflns 5223 Completeness (_total/calc) 170.32% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3673 Fraction of Friedel pairs measured 0.703 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

2,5-Dimethyl-7-phenylsulfonyl-5,6-dihydroindolo[2,3-c]benzazepin-12-one top
Crystal data top
C24H20N2O3SF(000) = 1744
Mr = 416.48Dx = 1.360 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 8072 reflections
a = 15.6032 (7) Åθ = 2.2–28.3°
b = 15.9227 (7) ŵ = 0.19 mm1
c = 16.3694 (7) ÅT = 293 K
V = 4066.9 (3) Å3Block, yellow
Z = 80.50 × 0.40 × 0.40 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
8896 independent reflections
Radiation source: fine-focus sealed tube6111 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
Detector resolution: 8.33 pixels mm-1θmax = 28.3°, θmin = 2.2°
ω scansh = 1920
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 2120
Tmin = 0.912, Tmax = 0.929l = 2114
24897 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.123 w = 1/[σ2(Fo2) + (0.0538P)2 + 0.5548P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
8896 reflectionsΔρmax = 0.19 e Å3
545 parametersΔρmin = 0.29 e Å3
1 restraintAbsolute structure: Flack (1983), with 3692 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (7)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1A0.01736 (5)0.28150 (5)0.37115 (5)0.0529 (2)
O1A0.02119 (15)0.22081 (16)0.43427 (15)0.0704 (7)
O2A0.06342 (14)0.30649 (17)0.33898 (14)0.0720 (7)
O3A0.28072 (17)0.13245 (18)0.13099 (16)0.0859 (8)
N1A0.07307 (16)0.24223 (16)0.29236 (15)0.0487 (6)
N2A0.19436 (18)0.07462 (17)0.37690 (18)0.0635 (7)
C1A0.14758 (18)0.19336 (19)0.29758 (19)0.0461 (7)
C2A0.17407 (19)0.17330 (19)0.22067 (18)0.0462 (7)
C3A0.11830 (19)0.21375 (18)0.16356 (18)0.0476 (7)
C4A0.1127 (2)0.2137 (2)0.0786 (2)0.0537 (8)
H4A0.15360.18540.04770.064*
C5A0.0474 (2)0.2549 (2)0.0408 (2)0.0612 (9)
H5A0.04390.25460.01600.073*
C6A0.0143 (2)0.2975 (2)0.0866 (2)0.0631 (9)
H6A0.05840.32540.05970.076*
C7A0.0113 (2)0.2993 (2)0.1708 (2)0.0584 (8)
H7A0.05220.32800.20130.070*
C8A0.0553 (2)0.25652 (19)0.20775 (18)0.0461 (7)
C9A0.07367 (19)0.3714 (2)0.40210 (18)0.0490 (7)
C10A0.1184 (2)0.3691 (2)0.4749 (2)0.0568 (8)
H10A0.12120.32000.50550.068*
C11A0.1588 (2)0.4410 (3)0.5012 (3)0.0732 (10)
H11A0.18940.44040.54990.088*
C12A0.1543 (3)0.5127 (3)0.4569 (3)0.0848 (12)
H12A0.18120.56090.47610.102*
C13A0.1107 (3)0.5152 (3)0.3844 (3)0.0838 (12)
H13A0.10940.56450.35390.101*
C14A0.0683 (2)0.4437 (2)0.3563 (2)0.0705 (10)
H14A0.03720.44490.30780.085*
C15A0.1931 (2)0.16540 (19)0.3730 (2)0.0550 (7)
H15A0.25130.18670.37270.066*
H15B0.16420.18770.42080.066*
C16A0.2532 (2)0.0299 (2)0.3306 (2)0.0576 (8)
C17A0.2854 (2)0.0565 (2)0.2544 (2)0.0529 (8)
C18A0.2499 (2)0.1223 (2)0.2001 (2)0.0564 (8)
C19A0.2842 (3)0.0469 (2)0.3620 (3)0.0775 (11)
H19A0.26020.06880.40950.093*
C20A0.3492 (3)0.0902 (2)0.3238 (3)0.0838 (13)
H20A0.36890.13990.34700.101*
C21A0.3859 (2)0.0622 (2)0.2524 (3)0.0721 (10)
C22A0.3533 (2)0.0093 (2)0.2201 (2)0.0630 (9)
H22A0.37730.02880.17170.076*
C23A0.1333 (3)0.0344 (3)0.4296 (4)0.1098 (17)
H23A0.12620.02310.41320.165*
H23B0.07930.06300.42600.165*
H23C0.15360.03630.48500.165*
C24A0.4565 (3)0.1117 (3)0.2124 (3)0.0952 (14)
H24A0.49560.07390.18590.143*
H24B0.43240.14930.17280.143*
H24C0.48670.14340.25320.143*
S1B0.27578 (5)0.23163 (5)0.60740 (5)0.04939 (19)
O1B0.30160 (16)0.28066 (15)0.53920 (14)0.0657 (6)
O2B0.18806 (13)0.22955 (15)0.63130 (15)0.0650 (6)
O3B0.53593 (15)0.36043 (18)0.86129 (18)0.0851 (8)
N1B0.32992 (16)0.26883 (15)0.68838 (15)0.0471 (6)
N2B0.46427 (16)0.43268 (16)0.61366 (17)0.0563 (7)
C1B0.40757 (18)0.31434 (17)0.68863 (19)0.0439 (7)
C2B0.43115 (18)0.32925 (19)0.76648 (18)0.0472 (7)
C3B0.36992 (19)0.28951 (18)0.82018 (19)0.0473 (7)
C4B0.3631 (2)0.2827 (2)0.9055 (2)0.0600 (9)
H4B0.40420.30660.93950.072*
C5B0.2944 (2)0.2400 (2)0.9377 (2)0.0663 (10)
H5B0.28910.23520.99400.080*
C6B0.2333 (2)0.2043 (2)0.8882 (2)0.0658 (9)
H6B0.18770.17580.91210.079*
C7B0.2375 (2)0.2094 (2)0.8035 (2)0.0586 (8)
H7B0.19590.18520.77030.070*
C8B0.3066 (2)0.2524 (2)0.7712 (2)0.0490 (7)
C9B0.31193 (18)0.12840 (19)0.59465 (18)0.0477 (7)
C10B0.3761 (2)0.1130 (2)0.5397 (3)0.0830 (13)
H10B0.39990.15640.50920.100*
C11B0.4047 (3)0.0314 (3)0.5306 (4)0.1086 (19)
H11B0.44950.02000.49490.130*
C12B0.3684 (3)0.0319 (3)0.5727 (3)0.0955 (15)
H12B0.38690.08670.56420.115*
C13B0.3062 (3)0.0165 (3)0.6265 (4)0.1057 (16)
H13B0.28290.06060.65640.127*
C14B0.2758 (3)0.0646 (2)0.6384 (3)0.0803 (12)
H14B0.23180.07520.67530.096*
C15B0.46064 (18)0.34191 (19)0.6176 (2)0.0519 (7)
H15C0.51820.31950.62300.062*
H15D0.43610.32010.56750.062*
C16B0.51516 (19)0.4766 (2)0.6672 (2)0.0541 (8)
C17B0.54235 (18)0.4473 (2)0.74515 (19)0.0499 (7)
C18B0.50691 (19)0.3766 (2)0.7938 (2)0.0536 (8)
C19B0.5456 (2)0.5566 (2)0.6429 (3)0.0688 (10)
H19B0.52650.57920.59380.083*
C20B0.6022 (2)0.6019 (2)0.6896 (3)0.0771 (12)
H20B0.62100.65370.67050.093*
C21B0.6321 (2)0.5731 (2)0.7637 (3)0.0655 (9)
C22B0.60240 (18)0.4970 (2)0.7893 (2)0.0572 (8)
H22B0.62270.47620.83870.069*
C23B0.4102 (3)0.4745 (3)0.5551 (3)0.0969 (15)
H23D0.41610.53420.56100.145*
H23E0.35150.45880.56430.145*
H23F0.42680.45830.50080.145*
C24B0.6932 (3)0.6250 (3)0.8153 (3)0.0913 (14)
H24D0.72070.58950.85480.137*
H24E0.66170.66830.84300.137*
H24F0.73580.65020.78070.137*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0491 (4)0.0657 (5)0.0439 (4)0.0056 (4)0.0102 (4)0.0042 (4)
O1A0.0816 (17)0.0783 (17)0.0514 (14)0.0139 (13)0.0252 (12)0.0057 (12)
O2A0.0461 (13)0.1039 (19)0.0659 (16)0.0028 (12)0.0082 (11)0.0156 (13)
O3A0.0864 (18)0.110 (2)0.0611 (16)0.0339 (16)0.0263 (14)0.0148 (15)
N1A0.0499 (15)0.0549 (16)0.0414 (15)0.0035 (12)0.0005 (11)0.0051 (11)
N2A0.0729 (18)0.0606 (17)0.0570 (18)0.0050 (14)0.0083 (15)0.0122 (15)
C1A0.0441 (16)0.0475 (17)0.0468 (17)0.0101 (13)0.0031 (13)0.0023 (13)
C2A0.0486 (17)0.0488 (17)0.0411 (17)0.0096 (13)0.0005 (13)0.0021 (13)
C3A0.0541 (18)0.0479 (18)0.0409 (17)0.0137 (14)0.0015 (14)0.0001 (13)
C4A0.0577 (19)0.059 (2)0.0442 (18)0.0078 (16)0.0085 (14)0.0029 (14)
C5A0.074 (2)0.072 (2)0.0377 (19)0.0131 (19)0.0005 (18)0.0000 (15)
C6A0.061 (2)0.067 (2)0.061 (2)0.0100 (17)0.0117 (17)0.0071 (16)
C7A0.0585 (19)0.059 (2)0.058 (2)0.0049 (16)0.0002 (16)0.0064 (16)
C8A0.0462 (18)0.0518 (18)0.0405 (18)0.0090 (14)0.0006 (14)0.0020 (13)
C9A0.0482 (17)0.0569 (19)0.0420 (17)0.0092 (14)0.0077 (13)0.0070 (13)
C10A0.0586 (19)0.062 (2)0.0498 (19)0.0136 (16)0.0033 (15)0.0126 (15)
C11A0.071 (2)0.075 (3)0.074 (3)0.008 (2)0.0123 (19)0.022 (2)
C12A0.086 (3)0.077 (3)0.092 (3)0.006 (2)0.001 (2)0.029 (3)
C13A0.103 (3)0.063 (2)0.085 (3)0.006 (2)0.002 (3)0.010 (2)
C14A0.084 (2)0.069 (2)0.059 (2)0.0023 (19)0.0123 (19)0.0039 (18)
C15A0.0633 (19)0.0578 (19)0.0439 (17)0.0047 (15)0.0006 (16)0.0055 (15)
C16A0.064 (2)0.0493 (19)0.059 (2)0.0112 (16)0.0089 (17)0.0009 (15)
C17A0.0538 (18)0.0497 (18)0.055 (2)0.0059 (15)0.0049 (15)0.0095 (15)
C18A0.056 (2)0.062 (2)0.052 (2)0.0028 (16)0.0071 (15)0.0068 (15)
C19A0.092 (3)0.058 (2)0.082 (3)0.008 (2)0.001 (2)0.008 (2)
C20A0.092 (3)0.047 (2)0.113 (4)0.001 (2)0.033 (3)0.002 (2)
C21A0.075 (2)0.056 (2)0.085 (3)0.003 (2)0.018 (2)0.010 (2)
C22A0.060 (2)0.060 (2)0.069 (2)0.0048 (17)0.0072 (17)0.0137 (18)
C23A0.113 (4)0.086 (3)0.130 (4)0.014 (3)0.042 (3)0.024 (3)
C24A0.089 (3)0.076 (3)0.120 (4)0.024 (2)0.016 (3)0.023 (3)
S1B0.0438 (4)0.0566 (4)0.0478 (5)0.0031 (3)0.0056 (3)0.0020 (4)
O1B0.0733 (15)0.0703 (16)0.0537 (15)0.0047 (12)0.0093 (12)0.0121 (12)
O2B0.0421 (11)0.0823 (16)0.0705 (16)0.0092 (11)0.0056 (10)0.0002 (12)
O3B0.0653 (15)0.121 (2)0.0690 (17)0.0257 (14)0.0230 (13)0.0342 (16)
N1B0.0495 (15)0.0498 (14)0.0420 (15)0.0038 (11)0.0022 (11)0.0012 (11)
N2B0.0575 (15)0.0556 (16)0.0557 (17)0.0034 (12)0.0033 (13)0.0129 (14)
C1B0.0418 (16)0.0402 (16)0.0497 (18)0.0085 (12)0.0007 (13)0.0016 (13)
C2B0.0433 (16)0.0512 (17)0.0470 (18)0.0078 (13)0.0003 (13)0.0051 (14)
C3B0.0462 (16)0.0467 (18)0.0489 (19)0.0064 (13)0.0023 (13)0.0052 (13)
C4B0.062 (2)0.068 (2)0.051 (2)0.0004 (17)0.0005 (15)0.0076 (16)
C5B0.068 (2)0.080 (3)0.051 (2)0.0015 (19)0.0112 (19)0.0113 (18)
C6B0.059 (2)0.078 (2)0.060 (2)0.0126 (18)0.0157 (17)0.0080 (18)
C7B0.0532 (19)0.068 (2)0.055 (2)0.0067 (17)0.0058 (15)0.0006 (16)
C8B0.0479 (17)0.0490 (17)0.050 (2)0.0050 (13)0.0042 (16)0.0032 (14)
C9B0.0413 (15)0.0575 (18)0.0443 (17)0.0028 (13)0.0011 (13)0.0017 (14)
C10B0.075 (2)0.064 (2)0.109 (3)0.0149 (19)0.043 (2)0.011 (2)
C11B0.077 (3)0.081 (3)0.168 (5)0.003 (2)0.055 (3)0.030 (3)
C12B0.082 (3)0.065 (3)0.139 (5)0.009 (2)0.005 (3)0.020 (3)
C13B0.121 (4)0.056 (2)0.140 (5)0.006 (2)0.029 (4)0.018 (3)
C14B0.091 (3)0.066 (2)0.084 (3)0.004 (2)0.034 (2)0.0031 (19)
C15B0.0468 (16)0.0585 (19)0.0503 (18)0.0015 (14)0.0050 (14)0.0044 (15)
C16B0.0425 (16)0.0525 (19)0.067 (2)0.0052 (14)0.0038 (15)0.0012 (16)
C17B0.0404 (16)0.0521 (18)0.057 (2)0.0104 (14)0.0013 (13)0.0017 (14)
C18B0.0403 (16)0.064 (2)0.057 (2)0.0036 (14)0.0014 (15)0.0083 (16)
C19B0.059 (2)0.057 (2)0.090 (3)0.0063 (17)0.0042 (19)0.0149 (19)
C20B0.054 (2)0.0445 (19)0.133 (4)0.0011 (16)0.000 (2)0.008 (2)
C21B0.0493 (18)0.051 (2)0.096 (3)0.0054 (16)0.0072 (19)0.0094 (19)
C22B0.0402 (16)0.064 (2)0.068 (2)0.0053 (15)0.0007 (15)0.0093 (17)
C23B0.090 (3)0.086 (3)0.115 (4)0.007 (2)0.039 (3)0.030 (3)
C24B0.070 (2)0.070 (3)0.134 (4)0.008 (2)0.014 (2)0.020 (2)
Geometric parameters (Å, º) top
S1A—O1A1.416 (3)S1B—O1B1.421 (2)
S1A—O2A1.423 (2)S1B—O2B1.424 (2)
S1A—N1A1.676 (3)S1B—N1B1.680 (3)
S1A—C9A1.754 (3)S1B—C9B1.750 (3)
O3A—C18A1.240 (4)O3B—C18B1.222 (4)
N1A—C1A1.402 (4)N1B—C1B1.412 (4)
N1A—C8A1.431 (4)N1B—C8B1.428 (4)
N2A—C16A1.387 (4)N2B—C16B1.374 (4)
N2A—C23A1.437 (5)N2B—C23B1.441 (5)
N2A—C15A1.447 (4)N2B—C15B1.448 (4)
C1A—C2A1.363 (4)C1B—C2B1.348 (4)
C1A—C15A1.492 (4)C1B—C15B1.493 (4)
C2A—C3A1.430 (4)C2B—C3B1.444 (4)
C2A—C18A1.474 (4)C2B—C18B1.472 (4)
C3A—C4A1.393 (4)C3B—C8B1.402 (4)
C3A—C8A1.397 (4)C3B—C4B1.405 (4)
C4A—C5A1.361 (5)C4B—C5B1.375 (5)
C4A—H4A0.93C4B—H4B0.93
C5A—C6A1.396 (5)C5B—C6B1.374 (5)
C5A—H5A0.93C5B—H5B0.93
C6A—C7A1.380 (5)C6B—C7B1.390 (5)
C6A—H6A0.93C6B—H6B0.93
C7A—C8A1.383 (5)C7B—C8B1.382 (4)
C7A—H7A0.93C7B—H7B0.93
C9A—C14A1.377 (5)C9B—C14B1.364 (4)
C9A—C10A1.382 (4)C9B—C10B1.368 (4)
C10A—C11A1.376 (5)C10B—C11B1.382 (6)
C10A—H10A0.93C10B—H10B0.93
C11A—C12A1.353 (6)C11B—C12B1.345 (7)
C11A—H11A0.93C11B—H11B0.93
C12A—C13A1.369 (6)C12B—C13B1.333 (6)
C12A—H12A0.93C12B—H12B0.93
C13A—C14A1.394 (5)C13B—C14B1.390 (6)
C13A—H13A0.93C13B—H13B0.93
C14A—H14A0.93C14B—H14B0.93
C15A—H15A0.97C15B—H15C0.97
C15A—H15B0.97C15B—H15D0.97
C16A—C17A1.410 (5)C16B—C19B1.415 (5)
C16A—C19A1.412 (5)C16B—C17B1.423 (4)
C17A—C22A1.416 (5)C17B—C22B1.424 (4)
C17A—C18A1.481 (5)C17B—C18B1.485 (4)
C19A—C20A1.376 (6)C19B—C20B1.373 (5)
C19A—H19A0.93C19B—H19B0.93
C20A—C21A1.377 (6)C20B—C21B1.378 (6)
C20A—H20A0.93C20B—H20B0.93
C21A—C22A1.353 (5)C21B—C22B1.364 (5)
C21A—C24A1.504 (5)C21B—C24B1.518 (5)
C22A—H22A0.93C22B—H22B0.93
C23A—H23A0.96C23B—H23D0.96
C23A—H23B0.96C23B—H23E0.96
C23A—H23C0.96C23B—H23F0.96
C24A—H24A0.96C24B—H24D0.96
C24A—H24B0.96C24B—H24E0.96
C24A—H24C0.96C24B—H24F0.96
O1A—S1A—O2A119.89 (15)O1B—S1B—O2B120.09 (14)
O1A—S1A—N1A106.55 (14)O1B—S1B—N1B106.48 (13)
O2A—S1A—N1A106.20 (13)O2B—S1B—N1B105.95 (13)
O1A—S1A—C9A108.96 (15)O1B—S1B—C9B109.33 (15)
O2A—S1A—C9A108.81 (15)O2B—S1B—C9B108.71 (14)
N1A—S1A—C9A105.48 (13)N1B—S1B—C9B105.26 (13)
C1A—N1A—C8A107.9 (2)C1B—N1B—C8B108.0 (2)
C1A—N1A—S1A126.2 (2)C1B—N1B—S1B127.9 (2)
C8A—N1A—S1A125.8 (2)C8B—N1B—S1B123.8 (2)
C16A—N2A—C23A122.6 (3)C16B—N2B—C23B121.9 (3)
C16A—N2A—C15A119.8 (3)C16B—N2B—C15B120.2 (3)
C23A—N2A—C15A117.6 (3)C23B—N2B—C15B117.9 (3)
C2A—C1A—N1A109.0 (3)C2B—C1B—N1B109.1 (2)
C2A—C1A—C15A123.4 (3)C2B—C1B—C15B122.2 (3)
N1A—C1A—C15A127.6 (3)N1B—C1B—C15B128.6 (3)
C1A—C2A—C3A108.3 (3)C1B—C2B—C3B108.5 (3)
C1A—C2A—C18A125.7 (3)C1B—C2B—C18B126.6 (3)
C3A—C2A—C18A126.0 (3)C3B—C2B—C18B124.8 (3)
C4A—C3A—C8A118.2 (3)C8B—C3B—C4B118.8 (3)
C4A—C3A—C2A133.6 (3)C8B—C3B—C2B107.6 (3)
C8A—C3A—C2A108.0 (3)C4B—C3B—C2B133.5 (3)
C5A—C4A—C3A120.1 (3)C5B—C4B—C3B118.5 (3)
C5A—C4A—H4A120.0C5B—C4B—H4B120.7
C3A—C4A—H4A120.0C3B—C4B—H4B120.7
C4A—C5A—C6A120.4 (3)C6B—C5B—C4B121.4 (4)
C4A—C5A—H5A119.8C6B—C5B—H5B119.3
C6A—C5A—H5A119.8C4B—C5B—H5B119.3
C7A—C6A—C5A121.6 (3)C5B—C6B—C7B122.0 (3)
C7A—C6A—H6A119.2C5B—C6B—H6B119.0
C5A—C6A—H6A119.2C7B—C6B—H6B119.0
C6A—C7A—C8A116.9 (3)C8B—C7B—C6B116.6 (3)
C6A—C7A—H7A121.6C8B—C7B—H7B121.7
C8A—C7A—H7A121.6C6B—C7B—H7B121.7
C7A—C8A—C3A122.8 (3)C7B—C8B—C3B122.7 (3)
C7A—C8A—N1A130.4 (3)C7B—C8B—N1B130.7 (3)
C3A—C8A—N1A106.7 (3)C3B—C8B—N1B106.6 (3)
C14A—C9A—C10A121.5 (3)C14B—C9B—C10B120.9 (3)
C14A—C9A—S1A119.6 (2)C14B—C9B—S1B120.2 (2)
C10A—C9A—S1A118.7 (3)C10B—C9B—S1B118.9 (3)
C11A—C10A—C9A118.6 (3)C9B—C10B—C11B118.4 (4)
C11A—C10A—H10A120.7C9B—C10B—H10B120.8
C9A—C10A—H10A120.7C11B—C10B—H10B120.8
C12A—C11A—C10A120.7 (4)C12B—C11B—C10B120.9 (4)
C12A—C11A—H11A119.6C12B—C11B—H11B119.6
C10A—C11A—H11A119.6C10B—C11B—H11B119.6
C11A—C12A—C13A121.0 (4)C13B—C12B—C11B120.5 (4)
C11A—C12A—H12A119.5C13B—C12B—H12B119.8
C13A—C12A—H12A119.5C11B—C12B—H12B119.8
C12A—C13A—C14A119.9 (4)C12B—C13B—C14B120.7 (4)
C12A—C13A—H13A120.1C12B—C13B—H13B119.6
C14A—C13A—H13A120.1C14B—C13B—H13B119.6
C9A—C14A—C13A118.3 (3)C9B—C14B—C13B118.5 (4)
C9A—C14A—H14A120.9C9B—C14B—H14B120.7
C13A—C14A—H14A120.9C13B—C14B—H14B120.7
N2A—C15A—C1A109.9 (3)N2B—C15B—C1B110.5 (2)
N2A—C15A—H15A109.7N2B—C15B—H15C109.6
C1A—C15A—H15A109.7C1B—C15B—H15C109.6
N2A—C15A—H15B109.7N2B—C15B—H15D109.6
C1A—C15A—H15B109.7C1B—C15B—H15D109.6
H15A—C15A—H15B108.2H15C—C15B—H15D108.1
N2A—C16A—C17A124.4 (3)N2B—C16B—C19B118.2 (3)
N2A—C16A—C19A118.2 (3)N2B—C16B—C17B125.2 (3)
C17A—C16A—C19A117.4 (3)C19B—C16B—C17B116.6 (3)
C16A—C17A—C22A117.2 (3)C16B—C17B—C22B117.9 (3)
C16A—C17A—C18A127.6 (3)C16B—C17B—C18B128.2 (3)
C22A—C17A—C18A114.7 (3)C22B—C17B—C18B113.2 (3)
O3A—C18A—C2A116.6 (3)O3B—C18B—C2B117.6 (3)
O3A—C18A—C17A119.7 (3)O3B—C18B—C17B120.5 (3)
C2A—C18A—C17A123.5 (3)C2B—C18B—C17B121.5 (3)
C20A—C19A—C16A121.4 (4)C20B—C19B—C16B122.2 (4)
C20A—C19A—H19A119.3C20B—C19B—H19B118.9
C16A—C19A—H19A119.3C16B—C19B—H19B118.9
C19A—C20A—C21A122.1 (4)C19B—C20B—C21B122.2 (3)
C19A—C20A—H20A119.0C19B—C20B—H20B118.9
C21A—C20A—H20A119.0C21B—C20B—H20B118.9
C22A—C21A—C20A116.5 (4)C22B—C21B—C20B116.8 (3)
C22A—C21A—C24A123.1 (4)C22B—C21B—C24B121.8 (4)
C20A—C21A—C24A120.3 (4)C20B—C21B—C24B121.4 (4)
C21A—C22A—C17A125.0 (4)C21B—C22B—C17B124.2 (3)
C21A—C22A—H22A117.5C21B—C22B—H22B117.9
C17A—C22A—H22A117.5C17B—C22B—H22B117.9
N2A—C23A—H23A109.5N2B—C23B—H23D109.5
N2A—C23A—H23B109.5N2B—C23B—H23E109.5
H23A—C23A—H23B109.5H23D—C23B—H23E109.5
N2A—C23A—H23C109.5N2B—C23B—H23F109.5
H23A—C23A—H23C109.5H23D—C23B—H23F109.5
H23B—C23A—H23C109.5H23E—C23B—H23F109.5
C21A—C24A—H24A109.5C21B—C24B—H24D109.5
C21A—C24A—H24B109.5C21B—C24B—H24E109.5
H24A—C24A—H24B109.5H24D—C24B—H24E109.5
C21A—C24A—H24C109.5C21B—C24B—H24F109.5
H24A—C24A—H24C109.5H24D—C24B—H24F109.5
H24B—C24A—H24C109.5H24E—C24B—H24F109.5
O1A—S1A—N1A—C1A35.9 (3)O1B—S1B—N1B—C1B22.7 (3)
O2A—S1A—N1A—C1A164.8 (2)O2B—S1B—N1B—C1B151.6 (2)
C9A—S1A—N1A—C1A79.8 (3)C9B—S1B—N1B—C1B93.3 (3)
O1A—S1A—N1A—C8A147.6 (2)O1B—S1B—N1B—C8B162.9 (2)
O2A—S1A—N1A—C8A18.7 (3)O2B—S1B—N1B—C8B33.9 (3)
C9A—S1A—N1A—C8A96.7 (3)C9B—S1B—N1B—C8B81.1 (3)
C8A—N1A—C1A—C2A3.1 (3)C8B—N1B—C1B—C2B2.3 (3)
S1A—N1A—C1A—C2A180.0 (2)S1B—N1B—C1B—C2B177.4 (2)
C8A—N1A—C1A—C15A177.3 (3)C8B—N1B—C1B—C15B176.0 (3)
S1A—N1A—C1A—C15A0.3 (4)S1B—N1B—C1B—C15B0.9 (4)
N1A—C1A—C2A—C3A3.2 (3)N1B—C1B—C2B—C3B2.6 (3)
C15A—C1A—C2A—C3A177.2 (3)C15B—C1B—C2B—C3B175.8 (3)
N1A—C1A—C2A—C18A179.8 (3)N1B—C1B—C2B—C18B178.3 (3)
C15A—C1A—C2A—C18A0.1 (5)C15B—C1B—C2B—C18B3.3 (5)
C1A—C2A—C3A—C4A177.5 (3)C1B—C2B—C3B—C8B2.0 (3)
C18A—C2A—C3A—C4A5.5 (6)C18B—C2B—C3B—C8B178.9 (3)
C1A—C2A—C3A—C8A2.1 (3)C1B—C2B—C3B—C4B178.4 (3)
C18A—C2A—C3A—C8A179.1 (3)C18B—C2B—C3B—C4B0.7 (5)
C8A—C3A—C4A—C5A0.3 (5)C8B—C3B—C4B—C5B0.2 (5)
C2A—C3A—C4A—C5A175.3 (3)C2B—C3B—C4B—C5B179.3 (3)
C3A—C4A—C5A—C6A0.1 (5)C3B—C4B—C5B—C6B0.1 (6)
C4A—C5A—C6A—C7A0.0 (5)C4B—C5B—C6B—C7B0.1 (6)
C5A—C6A—C7A—C8A0.4 (5)C5B—C6B—C7B—C8B0.1 (6)
C6A—C7A—C8A—C3A0.8 (5)C6B—C7B—C8B—C3B0.2 (5)
C6A—C7A—C8A—N1A175.7 (3)C6B—C7B—C8B—N1B179.8 (3)
C4A—C3A—C8A—C7A0.8 (5)C4B—C3B—C8B—C7B0.2 (5)
C2A—C3A—C8A—C7A177.0 (3)C2B—C3B—C8B—C7B179.4 (3)
C4A—C3A—C8A—N1A176.4 (3)C4B—C3B—C8B—N1B179.8 (3)
C2A—C3A—C8A—N1A0.2 (3)C2B—C3B—C8B—N1B0.6 (3)
C1A—N1A—C8A—C7A178.6 (3)C1B—N1B—C8B—C7B179.0 (3)
S1A—N1A—C8A—C7A4.4 (5)S1B—N1B—C8B—C7B3.6 (5)
C1A—N1A—C8A—C3A1.7 (3)C1B—N1B—C8B—C3B1.0 (3)
S1A—N1A—C8A—C3A178.7 (2)S1B—N1B—C8B—C3B176.4 (2)
O1A—S1A—C9A—C14A170.3 (3)O1B—S1B—C9B—C14B161.2 (3)
O2A—S1A—C9A—C14A37.9 (3)O2B—S1B—C9B—C14B28.4 (3)
N1A—S1A—C9A—C14A75.7 (3)N1B—S1B—C9B—C14B84.8 (3)
O1A—S1A—C9A—C10A5.9 (3)O1B—S1B—C9B—C10B18.1 (3)
O2A—S1A—C9A—C10A138.2 (2)O2B—S1B—C9B—C10B150.9 (3)
N1A—S1A—C9A—C10A108.2 (2)N1B—S1B—C9B—C10B95.9 (3)
C14A—C9A—C10A—C11A0.5 (5)C14B—C9B—C10B—C11B1.2 (6)
S1A—C9A—C10A—C11A176.6 (2)S1B—C9B—C10B—C11B179.5 (4)
C9A—C10A—C11A—C12A0.4 (5)C9B—C10B—C11B—C12B2.2 (8)
C10A—C11A—C12A—C13A1.0 (6)C10B—C11B—C12B—C13B2.5 (9)
C11A—C12A—C13A—C14A1.7 (6)C11B—C12B—C13B—C14B1.9 (9)
C10A—C9A—C14A—C13A1.2 (5)C10B—C9B—C14B—C13B0.6 (6)
S1A—C9A—C14A—C13A177.2 (3)S1B—C9B—C14B—C13B179.9 (4)
C12A—C13A—C14A—C9A1.7 (6)C12B—C13B—C14B—C9B0.9 (8)
C16A—N2A—C15A—C1A79.2 (4)C16B—N2B—C15B—C1B75.5 (3)
C23A—N2A—C15A—C1A100.8 (4)C23B—N2B—C15B—C1B101.5 (4)
C2A—C1A—C15A—N2A60.6 (4)C2B—C1B—C15B—N2B65.3 (4)
N1A—C1A—C15A—N2A119.0 (3)N1B—C1B—C15B—N2B116.6 (3)
C23A—N2A—C16A—C17A149.3 (4)C23B—N2B—C16B—C19B28.9 (5)
C15A—N2A—C16A—C17A30.7 (5)C15B—N2B—C16B—C19B154.2 (3)
C23A—N2A—C16A—C19A31.6 (5)C23B—N2B—C16B—C17B153.1 (4)
C15A—N2A—C16A—C19A148.4 (3)C15B—N2B—C16B—C17B23.8 (4)
N2A—C16A—C17A—C22A171.9 (3)N2B—C16B—C17B—C22B173.4 (3)
C19A—C16A—C17A—C22A7.2 (4)C19B—C16B—C17B—C22B4.7 (4)
N2A—C16A—C17A—C18A16.3 (5)N2B—C16B—C17B—C18B16.6 (5)
C19A—C16A—C17A—C18A164.6 (3)C19B—C16B—C17B—C18B165.3 (3)
C1A—C2A—C18A—O3A157.1 (3)C1B—C2B—C18B—O3B154.7 (3)
C3A—C2A—C18A—O3A19.5 (5)C3B—C2B—C18B—O3B24.3 (5)
C1A—C2A—C18A—C17A28.0 (5)C1B—C2B—C18B—C17B31.1 (5)
C3A—C2A—C18A—C17A155.4 (3)C3B—C2B—C18B—C17B150.0 (3)
C16A—C17A—C18A—O3A172.6 (3)C16B—C17B—C18B—O3B177.9 (3)
C22A—C17A—C18A—O3A0.6 (5)C22B—C17B—C18B—O3B7.5 (4)
C16A—C17A—C18A—C2A2.2 (5)C16B—C17B—C18B—C2B3.8 (5)
C22A—C17A—C18A—C2A174.1 (3)C22B—C17B—C18B—C2B166.6 (3)
N2A—C16A—C19A—C20A173.0 (3)N2B—C16B—C19B—C20B174.6 (3)
C17A—C16A—C19A—C20A6.1 (5)C17B—C16B—C19B—C20B3.6 (5)
C16A—C19A—C20A—C21A1.6 (6)C16B—C19B—C20B—C21B1.1 (6)
C19A—C20A—C21A—C22A1.7 (6)C19B—C20B—C21B—C22B0.3 (6)
C19A—C20A—C21A—C24A179.7 (4)C19B—C20B—C21B—C24B178.6 (3)
C20A—C21A—C22A—C17A0.3 (5)C20B—C21B—C22B—C17B1.0 (5)
C24A—C21A—C22A—C17A178.2 (3)C24B—C21B—C22B—C17B177.2 (3)
C16A—C17A—C22A—C21A4.3 (5)C16B—C17B—C22B—C21B3.6 (5)
C18A—C17A—C22A—C21A168.5 (3)C18B—C17B—C22B—C21B167.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4A—H4A···O3A0.932.553.047 (4)114
C4B—H4B···O3B0.932.573.054 (4)113
C7A—H7A···O2A0.932.292.873 (4)121
C7B—H7B···O2B0.932.392.940 (4)118
C10A—H10A···O1A0.932.512.884 (4)104
C10B—H10B···O1B0.932.552.912 (4)103
C15A—H15B···O1A0.972.302.997 (4)128
C15B—H15D···O1B0.972.242.959 (4)130
C22A—H22A···O3A0.932.332.694 (4)103
C22B—H22B···O3B0.932.322.682 (4)103
C11B—H11B···Cg1i0.932.853.687 (5)151
C12B—H12B···Cg2ii0.932.863.702 (5)151
C24B—H24D···Cg1iii0.962.903.698 (5)142
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+1/2, y1/2, z+1/2; (iii) x+1, y+1, z+1/2.
 

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