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In the title compound, C
39H
42BrNO
5S
2Si, the Si and S atoms have tetrahedrally geometry. In the crystal structure, the molecules form centrosymmetric dimers through rather long N—H
O hydrogen-bonding interactions.
Supporting information
CCDC reference: 259566
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.051
- wR factor = 0.130
- Data-to-parameter ratio = 19.9
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.93
Alert level C
ABSTM02_ALERT_3_C The ratio of Tmax/Tmin expected RT(exp) is > 1.10
Absorption corrections should be applied.
Tmin and Tmax expected: 0.746 0.839
RT(exp) = 1.125
PLAT057_ALERT_3_C Correction for Absorption Required RT(exp) ... 1.12
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.56 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.16 Ratio
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C36
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C5 -C10 1.37 Ang.
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
N-[(1
S,2S,3
R)-2-Bromo-3-(
tert-butyldiphenylsilyloxy)-1-phenyl-4-
(phenylsulfonyl)butyl]-4-methylbenzenesulfonamide
top
Crystal data top
C39H42BrNO5S2Si | F(000) = 1616 |
Mr = 776.86 | Dx = 1.345 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.9704 (8) Å | Cell parameters from 4427 reflections |
b = 19.5590 (12) Å | θ = 2.4–22.8° |
c = 14.1646 (9) Å | µ = 1.25 mm−1 |
β = 96.900 (1)° | T = 293 K |
V = 3842.4 (4) Å3 | Needle, colourless |
Z = 4 | 0.24 × 0.20 × 0.14 mm |
Data collection top
Bruker Smart APEX CCD area-detector diffractometer | 5593 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.040 |
Graphite monochromator | θmax = 28.0°, θmin = 1.8° |
ω scans | h = −17→18 |
23909 measured reflections | k = −25→23 |
8859 independent reflections | l = −18→18 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.072P)2 + 0.603P] where P = (Fo2 + 2Fc2)/3 |
8859 reflections | (Δ/σ)max = 0.003 |
446 parameters | Δρmax = 0.62 e Å−3 |
0 restraints | Δρmin = −0.56 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Br1 | 0.58188 (2) | 0.208667 (16) | 0.66847 (3) | 0.06261 (14) | |
C1 | 0.58772 (18) | 0.34824 (13) | 0.6178 (2) | 0.0370 (6) | |
H1 | 0.6103 | 0.3504 | 0.6860 | 0.044* | |
C2 | 0.51861 (18) | 0.28690 (13) | 0.6006 (2) | 0.0373 (6) | |
H2 | 0.5132 | 0.2763 | 0.5326 | 0.045* | |
C3 | 0.41601 (18) | 0.29696 (13) | 0.62589 (18) | 0.0354 (6) | |
H3 | 0.3847 | 0.3326 | 0.5845 | 0.043* | |
C4 | 0.41414 (18) | 0.31874 (14) | 0.72899 (18) | 0.0380 (6) | |
H4A | 0.4644 | 0.3523 | 0.7456 | 0.046* | |
H4B | 0.4280 | 0.2794 | 0.7700 | 0.046* | |
C5 | 0.3265 (2) | 0.38390 (16) | 0.8678 (2) | 0.0443 (7) | |
C6 | 0.3651 (2) | 0.44778 (17) | 0.8859 (3) | 0.0581 (8) | |
H6 | 0.3771 | 0.4764 | 0.8362 | 0.070* | |
C7 | 0.3859 (2) | 0.4687 (2) | 0.9790 (3) | 0.0700 (10) | |
H7 | 0.4118 | 0.5120 | 0.9924 | 0.084* | |
C8 | 0.3690 (3) | 0.4268 (2) | 1.0510 (3) | 0.0796 (12) | |
H8 | 0.3845 | 0.4412 | 1.1135 | 0.095* | |
C9 | 0.3290 (3) | 0.3633 (2) | 1.0329 (3) | 0.0776 (11) | |
H9 | 0.3164 | 0.3351 | 1.0827 | 0.093* | |
C10 | 0.3080 (3) | 0.34193 (17) | 0.9405 (2) | 0.0592 (9) | |
H10 | 0.2811 | 0.2989 | 0.9274 | 0.071* | |
C11 | 0.67958 (19) | 0.50421 (14) | 0.63723 (19) | 0.0398 (6) | |
C12 | 0.7490 (2) | 0.50595 (16) | 0.7156 (2) | 0.0520 (8) | |
H12 | 0.7332 | 0.4945 | 0.7756 | 0.062* | |
C13 | 0.8410 (2) | 0.52472 (19) | 0.7036 (2) | 0.0643 (9) | |
H13 | 0.8875 | 0.5263 | 0.7564 | 0.077* | |
C14 | 0.8669 (2) | 0.54136 (18) | 0.6153 (2) | 0.0585 (9) | |
C15 | 0.7969 (2) | 0.53846 (16) | 0.5380 (2) | 0.0557 (8) | |
H15 | 0.8130 | 0.5491 | 0.4779 | 0.067* | |
C16 | 0.7035 (2) | 0.52010 (15) | 0.5481 (2) | 0.0488 (7) | |
H16 | 0.6570 | 0.5184 | 0.4954 | 0.059* | |
C17 | 0.9684 (2) | 0.5628 (2) | 0.6035 (3) | 0.0906 (13) | |
H17A | 1.0103 | 0.5238 | 0.6119 | 0.136* | |
H17B | 0.9897 | 0.5968 | 0.6501 | 0.136* | |
H17C | 0.9700 | 0.5813 | 0.5409 | 0.136* | |
C18 | 0.67524 (19) | 0.34150 (14) | 0.5646 (2) | 0.0446 (7) | |
C19 | 0.6638 (2) | 0.34411 (15) | 0.4664 (2) | 0.0566 (8) | |
H19 | 0.6023 | 0.3473 | 0.4333 | 0.068* | |
C20 | 0.7440 (3) | 0.34199 (18) | 0.4167 (3) | 0.0759 (11) | |
H20 | 0.7364 | 0.3436 | 0.3506 | 0.091* | |
C21 | 0.8340 (3) | 0.3376 (2) | 0.4662 (4) | 0.0909 (15) | |
H21 | 0.8877 | 0.3368 | 0.4333 | 0.109* | |
C22 | 0.8465 (3) | 0.3343 (2) | 0.5627 (4) | 0.0841 (13) | |
H22 | 0.9083 | 0.3308 | 0.5952 | 0.101* | |
C23 | 0.7665 (2) | 0.33618 (16) | 0.6127 (3) | 0.0629 (9) | |
H23 | 0.7749 | 0.3339 | 0.6787 | 0.075* | |
C24 | 0.3718 (2) | 0.22678 (15) | 0.41022 (19) | 0.0408 (7) | |
C25 | 0.4497 (2) | 0.19458 (19) | 0.3782 (2) | 0.0611 (9) | |
H25 | 0.4710 | 0.1532 | 0.4053 | 0.073* | |
C26 | 0.4964 (3) | 0.2222 (2) | 0.3073 (3) | 0.0801 (12) | |
H26 | 0.5494 | 0.1997 | 0.2878 | 0.096* | |
C27 | 0.4656 (3) | 0.2824 (2) | 0.2651 (3) | 0.0828 (13) | |
H27 | 0.4964 | 0.3006 | 0.2161 | 0.099* | |
C28 | 0.3897 (3) | 0.3152 (2) | 0.2954 (3) | 0.0777 (11) | |
H28 | 0.3686 | 0.3564 | 0.2675 | 0.093* | |
C29 | 0.3439 (3) | 0.28806 (17) | 0.3669 (2) | 0.0606 (9) | |
H29 | 0.2922 | 0.3117 | 0.3870 | 0.073* | |
C30 | 0.35169 (19) | 0.10265 (15) | 0.5414 (2) | 0.0444 (7) | |
C31 | 0.3542 (2) | 0.05377 (17) | 0.4708 (3) | 0.0609 (9) | |
H31 | 0.3445 | 0.0674 | 0.4075 | 0.073* | |
C32 | 0.3707 (3) | −0.0145 (2) | 0.4914 (4) | 0.0827 (13) | |
H32 | 0.3719 | −0.0460 | 0.4424 | 0.099* | |
C33 | 0.3850 (3) | −0.0355 (2) | 0.5830 (5) | 0.0902 (15) | |
H33 | 0.3955 | −0.0816 | 0.5968 | 0.108* | |
C34 | 0.3843 (3) | 0.0104 (2) | 0.6547 (3) | 0.0851 (13) | |
H34 | 0.3943 | −0.0042 | 0.7176 | 0.102* | |
C35 | 0.3684 (2) | 0.07973 (18) | 0.6344 (3) | 0.0642 (9) | |
H35 | 0.3690 | 0.1109 | 0.6840 | 0.077* | |
C36 | 0.1812 (2) | 0.19846 (15) | 0.5030 (2) | 0.0453 (7) | |
C37 | 0.1394 (2) | 0.15857 (19) | 0.4145 (2) | 0.0651 (10) | |
H37A | 0.0703 | 0.1595 | 0.4094 | 0.098* | |
H37B | 0.1615 | 0.1121 | 0.4197 | 0.098* | |
H37C | 0.1604 | 0.1792 | 0.3590 | 0.098* | |
C38 | 0.1465 (2) | 0.1650 (2) | 0.5910 (2) | 0.0657 (10) | |
H38A | 0.1711 | 0.1902 | 0.6469 | 0.099* | |
H38B | 0.1694 | 0.1187 | 0.5965 | 0.099* | |
H38C | 0.0773 | 0.1652 | 0.5846 | 0.099* | |
C39 | 0.1426 (2) | 0.27209 (19) | 0.4962 (3) | 0.0783 (11) | |
H39A | 0.1554 | 0.2919 | 0.4370 | 0.117* | |
H39B | 0.1740 | 0.2986 | 0.5480 | 0.117* | |
H39C | 0.0744 | 0.2717 | 0.4993 | 0.117* | |
N1 | 0.53386 (14) | 0.41190 (10) | 0.59082 (15) | 0.0362 (5) | |
H1A | 0.4889 | 0.4120 | 0.5436 | 0.043* | |
O1 | 0.2834 (2) | 0.41091 (16) | 0.68720 (17) | 0.0974 (10) | |
O2 | 0.23100 (18) | 0.30129 (17) | 0.74917 (19) | 0.1004 (11) | |
O3 | 0.36095 (13) | 0.23622 (10) | 0.61151 (12) | 0.0433 (5) | |
O4 | 0.55618 (14) | 0.46619 (10) | 0.74889 (13) | 0.0482 (5) | |
O5 | 0.49736 (13) | 0.53253 (9) | 0.60528 (13) | 0.0463 (5) | |
S1 | 0.30168 (6) | 0.35403 (5) | 0.74997 (6) | 0.0571 (2) | |
S2 | 0.56020 (5) | 0.48139 (3) | 0.65088 (5) | 0.03767 (17) | |
Si1 | 0.31707 (5) | 0.19352 (4) | 0.51599 (5) | 0.03609 (18) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0547 (2) | 0.03949 (19) | 0.0935 (3) | 0.00353 (15) | 0.00842 (18) | 0.01134 (17) |
C1 | 0.0363 (15) | 0.0338 (14) | 0.0398 (15) | −0.0003 (11) | −0.0001 (12) | 0.0045 (12) |
C2 | 0.0379 (15) | 0.0342 (15) | 0.0396 (15) | −0.0027 (11) | 0.0038 (12) | 0.0011 (12) |
C3 | 0.0321 (14) | 0.0381 (15) | 0.0354 (14) | −0.0077 (11) | 0.0009 (11) | −0.0026 (12) |
C4 | 0.0358 (14) | 0.0413 (15) | 0.0361 (15) | −0.0049 (12) | 0.0008 (11) | −0.0047 (12) |
C5 | 0.0419 (16) | 0.0513 (18) | 0.0399 (16) | 0.0046 (13) | 0.0048 (13) | −0.0116 (14) |
C6 | 0.0470 (18) | 0.057 (2) | 0.072 (2) | −0.0012 (15) | 0.0122 (16) | −0.0075 (18) |
C7 | 0.053 (2) | 0.064 (2) | 0.091 (3) | 0.0002 (17) | 0.0011 (19) | −0.037 (2) |
C8 | 0.076 (3) | 0.102 (4) | 0.056 (2) | 0.021 (2) | −0.007 (2) | −0.034 (2) |
C9 | 0.108 (3) | 0.082 (3) | 0.044 (2) | 0.018 (2) | 0.011 (2) | 0.0018 (19) |
C10 | 0.078 (2) | 0.0472 (19) | 0.051 (2) | 0.0033 (17) | 0.0044 (17) | −0.0033 (16) |
C11 | 0.0409 (15) | 0.0345 (15) | 0.0429 (16) | −0.0057 (12) | 0.0004 (12) | 0.0012 (12) |
C12 | 0.0480 (18) | 0.064 (2) | 0.0421 (17) | −0.0053 (15) | −0.0032 (14) | 0.0047 (15) |
C13 | 0.0434 (18) | 0.084 (3) | 0.061 (2) | −0.0112 (17) | −0.0144 (15) | 0.0021 (19) |
C14 | 0.0426 (18) | 0.065 (2) | 0.066 (2) | −0.0137 (15) | 0.0002 (16) | 0.0040 (17) |
C15 | 0.0503 (19) | 0.062 (2) | 0.055 (2) | −0.0106 (16) | 0.0047 (15) | 0.0098 (16) |
C16 | 0.0437 (17) | 0.0529 (19) | 0.0471 (18) | −0.0089 (14) | −0.0054 (13) | 0.0065 (14) |
C17 | 0.046 (2) | 0.121 (4) | 0.105 (3) | −0.019 (2) | 0.008 (2) | 0.010 (3) |
C18 | 0.0355 (15) | 0.0350 (15) | 0.064 (2) | −0.0021 (12) | 0.0081 (14) | 0.0026 (14) |
C19 | 0.058 (2) | 0.0481 (19) | 0.067 (2) | 0.0030 (15) | 0.0210 (17) | 0.0009 (16) |
C20 | 0.086 (3) | 0.059 (2) | 0.091 (3) | −0.001 (2) | 0.046 (2) | 0.000 (2) |
C21 | 0.065 (3) | 0.065 (3) | 0.154 (5) | −0.012 (2) | 0.059 (3) | −0.006 (3) |
C22 | 0.0350 (19) | 0.074 (3) | 0.144 (4) | −0.0012 (17) | 0.016 (2) | −0.001 (3) |
C23 | 0.0381 (18) | 0.057 (2) | 0.093 (3) | −0.0024 (15) | 0.0021 (17) | 0.0044 (19) |
C24 | 0.0415 (16) | 0.0481 (17) | 0.0327 (15) | −0.0046 (13) | 0.0038 (12) | −0.0033 (13) |
C25 | 0.053 (2) | 0.075 (2) | 0.058 (2) | 0.0022 (17) | 0.0190 (16) | 0.0092 (18) |
C26 | 0.068 (3) | 0.105 (3) | 0.073 (3) | 0.003 (2) | 0.035 (2) | 0.003 (2) |
C27 | 0.099 (3) | 0.104 (4) | 0.051 (2) | −0.029 (3) | 0.032 (2) | 0.002 (2) |
C28 | 0.114 (3) | 0.069 (3) | 0.053 (2) | −0.006 (2) | 0.022 (2) | 0.013 (2) |
C29 | 0.078 (2) | 0.058 (2) | 0.049 (2) | 0.0038 (18) | 0.0204 (17) | 0.0036 (16) |
C30 | 0.0354 (15) | 0.0444 (17) | 0.0515 (18) | −0.0069 (12) | −0.0017 (13) | −0.0001 (14) |
C31 | 0.053 (2) | 0.049 (2) | 0.081 (2) | −0.0025 (15) | 0.0110 (17) | −0.0102 (18) |
C32 | 0.059 (2) | 0.047 (2) | 0.145 (4) | 0.0002 (18) | 0.026 (3) | −0.017 (3) |
C33 | 0.046 (2) | 0.047 (2) | 0.175 (5) | 0.0034 (17) | 0.005 (3) | 0.018 (3) |
C34 | 0.068 (3) | 0.073 (3) | 0.108 (3) | −0.013 (2) | −0.019 (2) | 0.041 (3) |
C35 | 0.063 (2) | 0.059 (2) | 0.067 (2) | −0.0131 (17) | −0.0099 (17) | 0.0103 (18) |
C36 | 0.0362 (15) | 0.0521 (19) | 0.0471 (17) | −0.0055 (13) | 0.0021 (13) | −0.0079 (14) |
C37 | 0.052 (2) | 0.088 (3) | 0.051 (2) | −0.0126 (18) | −0.0092 (15) | −0.0104 (18) |
C38 | 0.0482 (19) | 0.097 (3) | 0.054 (2) | −0.0171 (18) | 0.0150 (15) | −0.0092 (19) |
C39 | 0.048 (2) | 0.071 (3) | 0.115 (3) | 0.0147 (18) | 0.003 (2) | −0.004 (2) |
N1 | 0.0301 (11) | 0.0348 (12) | 0.0412 (13) | −0.0030 (9) | −0.0062 (9) | 0.0001 (10) |
O1 | 0.114 (2) | 0.129 (3) | 0.0483 (14) | 0.0704 (19) | 0.0059 (14) | 0.0117 (15) |
O2 | 0.0532 (15) | 0.167 (3) | 0.0852 (19) | −0.0467 (17) | 0.0265 (13) | −0.0709 (19) |
O3 | 0.0480 (11) | 0.0464 (11) | 0.0359 (10) | −0.0193 (9) | 0.0071 (8) | −0.0059 (9) |
O4 | 0.0558 (13) | 0.0492 (12) | 0.0397 (11) | −0.0051 (10) | 0.0064 (9) | −0.0005 (9) |
O5 | 0.0445 (11) | 0.0407 (11) | 0.0520 (12) | 0.0049 (9) | −0.0013 (9) | −0.0012 (9) |
S1 | 0.0413 (4) | 0.0877 (7) | 0.0416 (4) | 0.0044 (4) | 0.0021 (3) | −0.0158 (4) |
S2 | 0.0378 (4) | 0.0357 (4) | 0.0386 (4) | −0.0031 (3) | 0.0011 (3) | −0.0001 (3) |
Si1 | 0.0349 (4) | 0.0393 (4) | 0.0338 (4) | −0.0052 (3) | 0.0032 (3) | −0.0031 (3) |
Geometric parameters (Å, º) top
Br1—C2 | 1.960 (3) | C22—C23 | 1.394 (5) |
C1—N1 | 1.481 (3) | C22—H22 | 0.9300 |
C1—C18 | 1.517 (4) | C23—H23 | 0.9300 |
C1—C2 | 1.541 (3) | C24—C25 | 1.380 (4) |
C1—H1 | 0.9800 | C24—C29 | 1.381 (4) |
C2—C3 | 1.531 (4) | C24—Si1 | 1.878 (3) |
C2—H2 | 0.9800 | C25—C26 | 1.373 (5) |
C3—O3 | 1.417 (3) | C25—H25 | 0.9300 |
C3—C4 | 1.525 (4) | C26—C27 | 1.368 (6) |
C3—H3 | 0.9800 | C26—H26 | 0.9300 |
C4—S1 | 1.773 (3) | C27—C28 | 1.352 (6) |
C4—H4A | 0.9700 | C27—H27 | 0.9300 |
C4—H4B | 0.9700 | C28—C29 | 1.369 (5) |
C5—C10 | 1.366 (4) | C28—H28 | 0.9300 |
C5—C6 | 1.373 (4) | C29—H29 | 0.9300 |
C5—S1 | 1.764 (3) | C30—C35 | 1.384 (4) |
C6—C7 | 1.378 (5) | C30—C31 | 1.387 (4) |
C6—H6 | 0.9300 | C30—Si1 | 1.866 (3) |
C7—C8 | 1.350 (5) | C31—C32 | 1.380 (5) |
C7—H7 | 0.9300 | C31—H31 | 0.9300 |
C8—C9 | 1.373 (5) | C32—C33 | 1.352 (6) |
C8—H8 | 0.9300 | C32—H32 | 0.9300 |
C9—C10 | 1.371 (5) | C33—C34 | 1.358 (6) |
C9—H9 | 0.9300 | C33—H33 | 0.9300 |
C10—H10 | 0.9300 | C34—C35 | 1.398 (5) |
C11—C16 | 1.380 (4) | C34—H34 | 0.9300 |
C11—C12 | 1.384 (4) | C35—H35 | 0.9300 |
C11—S2 | 1.759 (3) | C36—C37 | 1.531 (4) |
C12—C13 | 1.367 (4) | C36—C39 | 1.537 (4) |
C12—H12 | 0.9300 | C36—C38 | 1.537 (4) |
C13—C14 | 1.382 (4) | C36—Si1 | 1.887 (3) |
C13—H13 | 0.9300 | C37—H37A | 0.9600 |
C14—C15 | 1.380 (4) | C37—H37B | 0.9600 |
C14—C17 | 1.507 (4) | C37—H37C | 0.9600 |
C15—C16 | 1.377 (4) | C38—H38A | 0.9600 |
C15—H15 | 0.9300 | C38—H38B | 0.9600 |
C16—H16 | 0.9300 | C38—H38C | 0.9600 |
C17—H17A | 0.9600 | C39—H39A | 0.9600 |
C17—H17B | 0.9600 | C39—H39B | 0.9600 |
C17—H17C | 0.9600 | C39—H39C | 0.9600 |
C18—C23 | 1.376 (4) | N1—S2 | 1.622 (2) |
C18—C19 | 1.382 (4) | N1—H1A | 0.8600 |
C19—C20 | 1.394 (4) | O1—S1 | 1.428 (3) |
C19—H19 | 0.9300 | O2—S1 | 1.427 (3) |
C20—C21 | 1.367 (6) | O3—Si1 | 1.6446 (19) |
C20—H20 | 0.9300 | O4—S2 | 1.4275 (19) |
C21—C22 | 1.357 (6) | O5—S2 | 1.4325 (19) |
C21—H21 | 0.9300 | | |
| | | |
N1—C1—C18 | 111.1 (2) | C22—C23—H23 | 119.9 |
N1—C1—C2 | 108.9 (2) | C25—C24—C29 | 116.2 (3) |
C18—C1—C2 | 112.4 (2) | C25—C24—Si1 | 121.1 (2) |
N1—C1—H1 | 108.1 | C29—C24—Si1 | 122.3 (2) |
C18—C1—H1 | 108.1 | C26—C25—C24 | 121.6 (3) |
C2—C1—H1 | 108.1 | C26—C25—H25 | 119.2 |
C3—C2—C1 | 116.7 (2) | C24—C25—H25 | 119.2 |
C3—C2—Br1 | 111.43 (17) | C27—C26—C25 | 120.4 (4) |
C1—C2—Br1 | 107.06 (17) | C27—C26—H26 | 119.8 |
C3—C2—H2 | 107.1 | C25—C26—H26 | 119.8 |
C1—C2—H2 | 107.1 | C28—C27—C26 | 119.2 (3) |
Br1—C2—H2 | 107.1 | C28—C27—H27 | 120.4 |
O3—C3—C4 | 107.5 (2) | C26—C27—H27 | 120.4 |
O3—C3—C2 | 111.5 (2) | C27—C28—C29 | 120.3 (4) |
C4—C3—C2 | 112.6 (2) | C27—C28—H28 | 119.8 |
O3—C3—H3 | 108.4 | C29—C28—H28 | 119.8 |
C4—C3—H3 | 108.4 | C28—C29—C24 | 122.2 (3) |
C2—C3—H3 | 108.4 | C28—C29—H29 | 118.9 |
C3—C4—S1 | 112.75 (18) | C24—C29—H29 | 118.9 |
C3—C4—H4A | 109.0 | C35—C30—C31 | 116.5 (3) |
S1—C4—H4A | 109.0 | C35—C30—Si1 | 120.1 (2) |
C3—C4—H4B | 109.0 | C31—C30—Si1 | 123.1 (2) |
S1—C4—H4B | 109.0 | C32—C31—C30 | 122.2 (4) |
H4A—C4—H4B | 107.8 | C32—C31—H31 | 118.9 |
C10—C5—C6 | 120.8 (3) | C30—C31—H31 | 118.9 |
C10—C5—S1 | 118.8 (2) | C33—C32—C31 | 119.9 (4) |
C6—C5—S1 | 120.4 (3) | C33—C32—H32 | 120.0 |
C5—C6—C7 | 118.8 (3) | C31—C32—H32 | 120.0 |
C5—C6—H6 | 120.6 | C32—C33—C34 | 120.2 (4) |
C7—C6—H6 | 120.6 | C32—C33—H33 | 119.9 |
C8—C7—C6 | 120.4 (4) | C34—C33—H33 | 119.9 |
C8—C7—H7 | 119.8 | C33—C34—C35 | 120.2 (4) |
C6—C7—H7 | 119.8 | C33—C34—H34 | 119.9 |
C7—C8—C9 | 120.8 (4) | C35—C34—H34 | 119.9 |
C7—C8—H8 | 119.6 | C30—C35—C34 | 121.0 (4) |
C9—C8—H8 | 119.6 | C30—C35—H35 | 119.5 |
C8—C9—C10 | 119.4 (4) | C34—C35—H35 | 119.5 |
C8—C9—H9 | 120.3 | C37—C36—C39 | 109.2 (3) |
C10—C9—H9 | 120.3 | C37—C36—C38 | 108.7 (3) |
C5—C10—C9 | 119.8 (3) | C39—C36—C38 | 107.9 (3) |
C5—C10—H10 | 120.1 | C37—C36—Si1 | 109.5 (2) |
C9—C10—H10 | 120.1 | C39—C36—Si1 | 113.3 (2) |
C16—C11—C12 | 120.4 (3) | C38—C36—Si1 | 108.1 (2) |
C16—C11—S2 | 119.6 (2) | C36—C37—H37A | 109.5 |
C12—C11—S2 | 120.0 (2) | C36—C37—H37B | 109.5 |
C13—C12—C11 | 119.0 (3) | H37A—C37—H37B | 109.5 |
C13—C12—H12 | 120.5 | C36—C37—H37C | 109.5 |
C11—C12—H12 | 120.5 | H37A—C37—H37C | 109.5 |
C12—C13—C14 | 121.9 (3) | H37B—C37—H37C | 109.5 |
C12—C13—H13 | 119.0 | C36—C38—H38A | 109.5 |
C14—C13—H13 | 119.0 | C36—C38—H38B | 109.5 |
C15—C14—C13 | 118.1 (3) | H38A—C38—H38B | 109.5 |
C15—C14—C17 | 120.7 (3) | C36—C38—H38C | 109.5 |
C13—C14—C17 | 121.2 (3) | H38A—C38—H38C | 109.5 |
C16—C15—C14 | 121.2 (3) | H38B—C38—H38C | 109.5 |
C16—C15—H15 | 119.4 | C36—C39—H39A | 109.5 |
C14—C15—H15 | 119.4 | C36—C39—H39B | 109.5 |
C15—C16—C11 | 119.4 (3) | H39A—C39—H39B | 109.5 |
C15—C16—H16 | 120.3 | C36—C39—H39C | 109.5 |
C11—C16—H16 | 120.3 | H39A—C39—H39C | 109.5 |
C14—C17—H17A | 109.5 | H39B—C39—H39C | 109.5 |
C14—C17—H17B | 109.5 | C1—N1—S2 | 119.54 (17) |
H17A—C17—H17B | 109.5 | C1—N1—H1A | 120.2 |
C14—C17—H17C | 109.5 | S2—N1—H1A | 120.2 |
H17A—C17—H17C | 109.5 | C3—O3—Si1 | 133.35 (16) |
H17B—C17—H17C | 109.5 | O2—S1—O1 | 119.1 (2) |
C23—C18—C19 | 119.3 (3) | O2—S1—C5 | 107.71 (15) |
C23—C18—C1 | 121.0 (3) | O1—S1—C5 | 109.37 (16) |
C19—C18—C1 | 119.6 (3) | O2—S1—C4 | 110.08 (16) |
C18—C19—C20 | 120.3 (3) | O1—S1—C4 | 107.12 (15) |
C18—C19—H19 | 119.9 | C5—S1—C4 | 102.12 (13) |
C20—C19—H19 | 119.9 | O4—S2—O5 | 119.36 (12) |
C21—C20—C19 | 119.2 (4) | O4—S2—N1 | 107.62 (11) |
C21—C20—H20 | 120.4 | O5—S2—N1 | 105.10 (11) |
C19—C20—H20 | 120.4 | O4—S2—C11 | 107.95 (12) |
C22—C21—C20 | 121.3 (4) | O5—S2—C11 | 108.12 (12) |
C22—C21—H21 | 119.3 | N1—S2—C11 | 108.25 (12) |
C20—C21—H21 | 119.3 | O3—Si1—C30 | 105.24 (12) |
C21—C22—C23 | 119.7 (4) | O3—Si1—C24 | 109.46 (11) |
C21—C22—H22 | 120.2 | C30—Si1—C24 | 111.28 (13) |
C23—C22—H22 | 120.2 | O3—Si1—C36 | 108.98 (11) |
C18—C23—C22 | 120.2 (4) | C30—Si1—C36 | 107.58 (12) |
C18—C23—H23 | 119.9 | C24—Si1—C36 | 113.92 (13) |
| | | |
N1—C1—C2—C3 | −39.2 (3) | C31—C32—C33—C34 | −0.7 (6) |
C18—C1—C2—C3 | −162.8 (2) | C32—C33—C34—C35 | 0.2 (6) |
N1—C1—C2—Br1 | −164.84 (17) | C31—C30—C35—C34 | −1.6 (5) |
C18—C1—C2—Br1 | 71.6 (2) | Si1—C30—C35—C34 | 173.1 (3) |
C1—C2—C3—O3 | −177.1 (2) | C33—C34—C35—C30 | 1.0 (6) |
Br1—C2—C3—O3 | −53.7 (2) | C18—C1—N1—S2 | −90.7 (2) |
C1—C2—C3—C4 | −56.2 (3) | C2—C1—N1—S2 | 144.92 (18) |
Br1—C2—C3—C4 | 67.2 (2) | C4—C3—O3—Si1 | 167.12 (19) |
O3—C3—C4—S1 | −74.0 (2) | C2—C3—O3—Si1 | −69.1 (3) |
C2—C3—C4—S1 | 162.85 (18) | C10—C5—S1—O2 | 23.0 (3) |
C10—C5—C6—C7 | 0.7 (5) | C6—C5—S1—O2 | −157.9 (3) |
S1—C5—C6—C7 | −178.3 (2) | C10—C5—S1—O1 | 153.9 (3) |
C5—C6—C7—C8 | 0.3 (5) | C6—C5—S1—O1 | −27.1 (3) |
C6—C7—C8—C9 | −1.3 (6) | C10—C5—S1—C4 | −92.9 (3) |
C7—C8—C9—C10 | 1.3 (6) | C6—C5—S1—C4 | 86.1 (3) |
C6—C5—C10—C9 | −0.7 (5) | C3—C4—S1—O2 | 73.2 (2) |
S1—C5—C10—C9 | 178.3 (3) | C3—C4—S1—O1 | −57.7 (2) |
C8—C9—C10—C5 | −0.2 (5) | C3—C4—S1—C5 | −172.6 (2) |
C16—C11—C12—C13 | 1.1 (5) | C1—N1—S2—O4 | −53.2 (2) |
S2—C11—C12—C13 | −179.1 (3) | C1—N1—S2—O5 | 178.62 (18) |
C11—C12—C13—C14 | −0.6 (5) | C1—N1—S2—C11 | 63.3 (2) |
C12—C13—C14—C15 | −0.2 (5) | C16—C11—S2—O4 | 178.7 (2) |
C12—C13—C14—C17 | 179.3 (4) | C12—C11—S2—O4 | −1.1 (3) |
C13—C14—C15—C16 | 0.5 (5) | C16—C11—S2—O5 | −50.9 (3) |
C17—C14—C15—C16 | −178.9 (3) | C12—C11—S2—O5 | 129.3 (2) |
C14—C15—C16—C11 | −0.1 (5) | C16—C11—S2—N1 | 62.5 (3) |
C12—C11—C16—C15 | −0.7 (4) | C12—C11—S2—N1 | −117.3 (2) |
S2—C11—C16—C15 | 179.5 (2) | C3—O3—Si1—C30 | 131.7 (2) |
N1—C1—C18—C23 | 121.5 (3) | C3—O3—Si1—C24 | 12.1 (3) |
C2—C1—C18—C23 | −116.1 (3) | C3—O3—Si1—C36 | −113.1 (2) |
N1—C1—C18—C19 | −55.3 (3) | C35—C30—Si1—O3 | 25.4 (3) |
C2—C1—C18—C19 | 67.1 (3) | C31—C30—Si1—O3 | −160.2 (2) |
C23—C18—C19—C20 | −0.6 (4) | C35—C30—Si1—C24 | 143.9 (2) |
C1—C18—C19—C20 | 176.3 (3) | C31—C30—Si1—C24 | −41.7 (3) |
C18—C19—C20—C21 | −0.2 (5) | C35—C30—Si1—C36 | −90.7 (2) |
C19—C20—C21—C22 | 0.9 (6) | C31—C30—Si1—C36 | 83.7 (3) |
C20—C21—C22—C23 | −0.7 (6) | C25—C24—Si1—O3 | 97.1 (3) |
C19—C18—C23—C22 | 0.8 (5) | C29—C24—Si1—O3 | −75.8 (3) |
C1—C18—C23—C22 | −176.0 (3) | C25—C24—Si1—C30 | −18.8 (3) |
C21—C22—C23—C18 | −0.1 (6) | C29—C24—Si1—C30 | 168.3 (3) |
C29—C24—C25—C26 | 0.0 (5) | C25—C24—Si1—C36 | −140.6 (2) |
Si1—C24—C25—C26 | −173.3 (3) | C29—C24—Si1—C36 | 46.5 (3) |
C24—C25—C26—C27 | −1.1 (6) | C37—C36—Si1—O3 | −179.7 (2) |
C25—C26—C27—C28 | 1.4 (6) | C39—C36—Si1—O3 | 58.1 (3) |
C26—C27—C28—C29 | −0.6 (6) | C38—C36—Si1—O3 | −61.5 (2) |
C27—C28—C29—C24 | −0.5 (6) | C37—C36—Si1—C30 | −66.1 (2) |
C25—C24—C29—C28 | 0.8 (5) | C39—C36—Si1—C30 | 171.7 (2) |
Si1—C24—C29—C28 | 174.0 (3) | C38—C36—Si1—C30 | 52.1 (2) |
C35—C30—C31—C32 | 1.2 (5) | C37—C36—Si1—C24 | 57.7 (3) |
Si1—C30—C31—C32 | −173.4 (2) | C39—C36—Si1—C24 | −64.5 (3) |
C30—C31—C32—C33 | 0.0 (5) | C38—C36—Si1—C24 | 176.0 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O4 | 0.98 | 2.58 | 3.027 (5) | 108 |
C4—H4A···O4 | 0.97 | 2.57 | 3.493 (3) | 160 |
C10—H10···O2 | 0.93 | 2.54 | 2.904 (2) | 104 |
C12—H12···O4 | 0.93 | 2.52 | 2.896 (2) | 105 |
N1—H1A···O5i | 0.86 | 2.40 | 2.966 (3) | 124 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
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