In the title compound, C
39H
42BrNO
4S
2Si, the Si atom shows a tetrahedral geometry. The phenyl rings attached to the Si atom form a dihedral angle of 54.9 (1)°. The molecular packing is stabilized by N—H
O hydrogen bonds.
Supporting information
CCDC reference: 253035
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.054
- wR factor = 0.130
- Data-to-parameter ratio = 20.8
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.93
PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.13 Ratio
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.07 Ratio
PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors for C36
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.30
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) ..... 0 Ang.
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C19
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C21
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C5
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C17
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C20
PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. S1 .. 3.51 Ang.
2 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
10 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
9 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
2 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)-3-(
tert-Butyldiphenylsiloxy)-2-bromo-1-phenyl-4- (phenylsulfinyl)butyl]benzenesulfonamide
top
Crystal data top
C39H42BrNO4S2Si | F(000) = 1584 |
Mr = 760.86 | Dx = 1.284 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 20.0567 (11) Å | Cell parameters from 3196 reflections |
b = 8.2412 (5) Å | θ = 2.6–20.6° |
c = 23.8154 Å | µ = 1.22 mm−1 |
β = 91.263 (1)° | T = 293 K |
V = 3935.5 (4) Å3 | Block, colourless |
Z = 4 | 0.22 × 0.19 × 0.14 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 5188 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.056 |
Graphite monochromator | θmax = 28.0°, θmin = 1.7° |
ω scans | h = −18→26 |
24266 measured reflections | k = −10→10 |
9091 independent reflections | l = −30→25 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 0.95 | w = 1/[σ2(Fo2) + (0.072P)2 + 0.603P] where P = (Fo2 + 2Fc2)/3 |
9091 reflections | (Δ/σ)max < 0.014 |
437 parameters | Δρmax = 0.56 e Å−3 |
0 restraints | Δρmin = −0.24 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 | 0.195690 (19) | 0.95253 (4) | 0.023403 (15) | 0.05495 (14) | |
C1 | 0.28804 (17) | 0.8661 (4) | 0.11533 (14) | 0.0435 (8) | |
H1 | 0.2933 | 0.7989 | 0.1491 | 0.052* | |
C2 | 0.21916 (16) | 0.8219 (3) | 0.08976 (13) | 0.0399 (8) | |
H2 | 0.1865 | 0.8496 | 0.1182 | 0.048* | |
C3 | 0.20969 (16) | 0.6399 (3) | 0.07746 (13) | 0.0378 (7) | |
H3 | 0.2327 | 0.5784 | 0.1073 | 0.045* | |
C4 | 0.23618 (17) | 0.5846 (3) | 0.02171 (13) | 0.0398 (8) | |
H4A | 0.2809 | 0.6268 | 0.0170 | 0.048* | |
H4B | 0.2080 | 0.6260 | −0.0086 | 0.048* | |
C5 | 0.27878 (18) | 0.3485 (3) | −0.04644 (13) | 0.0428 (8) | |
C6 | 0.3462 (2) | 0.3253 (5) | −0.04780 (16) | 0.0636 (11) | |
H6 | 0.3715 | 0.3209 | −0.0146 | 0.076* | |
C7 | 0.3764 (2) | 0.3082 (6) | −0.0991 (2) | 0.0868 (14) | |
H7 | 0.4222 | 0.2920 | −0.1004 | 0.104* | |
C8 | 0.3396 (3) | 0.3151 (6) | −0.14761 (18) | 0.0846 (14) | |
H8 | 0.3604 | 0.3043 | −0.1819 | 0.102* | |
C9 | 0.2722 (3) | 0.3378 (6) | −0.14613 (18) | 0.0830 (14) | |
H9 | 0.2473 | 0.3434 | −0.1795 | 0.100* | |
C10 | 0.2410 (2) | 0.3525 (5) | −0.09549 (16) | 0.0669 (11) | |
H10 | 0.1950 | 0.3649 | −0.0944 | 0.080* | |
C11 | 0.34747 (17) | 0.8285 (4) | 0.08009 (15) | 0.0490 (9) | |
C12 | 0.3829 (2) | 0.6869 (5) | 0.08953 (19) | 0.0730 (12) | |
H12 | 0.3709 | 0.6176 | 0.1184 | 0.088* | |
C13 | 0.4360 (2) | 0.6482 (7) | 0.0561 (3) | 0.1003 (18) | |
H13 | 0.4594 | 0.5523 | 0.0625 | 0.120* | |
C14 | 0.4543 (2) | 0.7484 (8) | 0.0140 (3) | 0.1041 (18) | |
H14 | 0.4900 | 0.7211 | −0.0084 | 0.125* | |
C15 | 0.4202 (2) | 0.8896 (6) | 0.0047 (2) | 0.0861 (14) | |
H15 | 0.4329 | 0.9588 | −0.0240 | 0.103* | |
C16 | 0.3671 (2) | 0.9300 (5) | 0.03766 (17) | 0.0634 (11) | |
H16 | 0.3443 | 1.0267 | 0.0311 | 0.076* | |
C17 | 0.4086 (2) | 1.1084 (5) | 0.18138 (15) | 0.0581 (10) | |
C18 | 0.4539 (3) | 0.9992 (6) | 0.2014 (2) | 0.1008 (17) | |
H18 | 0.4397 | 0.9068 | 0.2201 | 0.121* | |
C19 | 0.5217 (3) | 1.0263 (8) | 0.1938 (3) | 0.123 (2) | |
H19 | 0.5524 | 0.9528 | 0.2089 | 0.147* | |
C20 | 0.5441 (3) | 1.1547 (8) | 0.1655 (3) | 0.1030 (17) | |
C21 | 0.4988 (3) | 1.2596 (8) | 0.1454 (3) | 0.121 (2) | |
H21 | 0.5133 | 1.3494 | 0.1254 | 0.146* | |
C22 | 0.4312 (2) | 1.2395 (6) | 0.1533 (2) | 0.1020 (17) | |
H22 | 0.4012 | 1.3162 | 0.1393 | 0.122* | |
C23 | 0.6188 (3) | 1.1812 (8) | 0.1569 (3) | 0.154 (3) | |
H23A | 0.6426 | 1.1656 | 0.1919 | 0.231* | |
H23B | 0.6261 | 1.2897 | 0.1437 | 0.231* | |
H23C | 0.6346 | 1.1050 | 0.1298 | 0.231* | |
C24 | 0.13825 (16) | 0.6306 (4) | 0.19891 (13) | 0.0463 (8) | |
C25 | 0.18754 (19) | 0.5316 (5) | 0.22251 (17) | 0.0640 (11) | |
H25 | 0.1976 | 0.4343 | 0.2048 | 0.077* | |
C26 | 0.2221 (2) | 0.5727 (6) | 0.2715 (2) | 0.0856 (15) | |
H26 | 0.2548 | 0.5040 | 0.2864 | 0.103* | |
C27 | 0.2076 (2) | 0.7152 (8) | 0.29746 (18) | 0.0876 (15) | |
H27 | 0.2300 | 0.7425 | 0.3308 | 0.105* | |
C28 | 0.1614 (2) | 0.8172 (6) | 0.27563 (19) | 0.0846 (15) | |
H28 | 0.1527 | 0.9152 | 0.2934 | 0.102* | |
C29 | 0.12676 (18) | 0.7756 (5) | 0.22655 (15) | 0.0639 (11) | |
H29 | 0.0950 | 0.8470 | 0.2118 | 0.077* | |
C30 | 0.02064 (17) | 0.7197 (4) | 0.12197 (14) | 0.0470 (8) | |
C31 | −0.02497 (19) | 0.7504 (5) | 0.16391 (16) | 0.0670 (11) | |
H31 | −0.0188 | 0.7010 | 0.1987 | 0.080* | |
C32 | −0.0789 (2) | 0.8516 (6) | 0.15552 (19) | 0.0817 (14) | |
H32 | −0.1080 | 0.8713 | 0.1846 | 0.098* | |
C33 | −0.0896 (2) | 0.9233 (5) | 0.1040 (2) | 0.0779 (13) | |
H33 | −0.1264 | 0.9903 | 0.0979 | 0.093* | |
C34 | −0.0460 (2) | 0.8958 (5) | 0.06166 (18) | 0.0676 (11) | |
H34 | −0.0530 | 0.9448 | 0.0268 | 0.081* | |
C35 | 0.00834 (18) | 0.7957 (4) | 0.07047 (15) | 0.0537 (9) | |
H35 | 0.0376 | 0.7785 | 0.0413 | 0.064* | |
C36 | 0.05932 (19) | 0.3617 (4) | 0.13002 (15) | 0.0546 (9) | |
C37 | 0.0108 (3) | 0.3323 (6) | 0.1767 (2) | 0.1000 (17) | |
H37A | −0.0036 | 0.2212 | 0.1758 | 0.150* | |
H37B | −0.0271 | 0.4024 | 0.1717 | 0.150* | |
H37C | 0.0323 | 0.3547 | 0.2123 | 0.150* | |
C38 | 0.0237 (3) | 0.3390 (6) | 0.07335 (19) | 0.119 (2) | |
H38A | 0.0057 | 0.2312 | 0.0710 | 0.179* | |
H38B | 0.0547 | 0.3550 | 0.0438 | 0.179* | |
H38C | −0.0119 | 0.4165 | 0.0696 | 0.179* | |
C39 | 0.1144 (3) | 0.2344 (5) | 0.1353 (2) | 0.1056 (17) | |
H39A | 0.1339 | 0.2380 | 0.1725 | 0.158* | |
H39B | 0.1482 | 0.2567 | 0.1083 | 0.158* | |
H39C | 0.0960 | 0.1287 | 0.1283 | 0.158* | |
N1 | 0.28566 (13) | 1.0346 (3) | 0.13554 (10) | 0.0448 (7) | |
H1A | 0.2641 | 1.1064 | 0.1162 | 0.054* | |
O1 | 0.28760 (12) | 0.3162 (3) | 0.06379 (9) | 0.0549 (6) | |
O2 | 0.14103 (11) | 0.5982 (2) | 0.07797 (8) | 0.0428 (5) | |
O3 | 0.31616 (15) | 0.9545 (3) | 0.23158 (10) | 0.0789 (8) | |
O4 | 0.29795 (13) | 1.2439 (3) | 0.20682 (11) | 0.0727 (8) | |
S1 | 0.23776 (5) | 0.36527 (9) | 0.01921 (3) | 0.0443 (2) | |
S2 | 0.32280 (5) | 1.08613 (11) | 0.19330 (4) | 0.0545 (3) | |
Si1 | 0.09182 (5) | 0.57629 (11) | 0.13268 (4) | 0.0423 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0625 (3) | 0.03766 (18) | 0.0639 (3) | 0.00354 (17) | −0.01743 (19) | 0.00606 (16) |
C1 | 0.049 (2) | 0.0371 (17) | 0.0437 (19) | 0.0048 (15) | −0.0060 (17) | 0.0027 (14) |
C2 | 0.042 (2) | 0.0386 (16) | 0.0390 (18) | 0.0026 (14) | 0.0038 (16) | 0.0012 (14) |
C3 | 0.0411 (19) | 0.0352 (16) | 0.0372 (18) | 0.0030 (14) | 0.0050 (15) | 0.0026 (13) |
C4 | 0.045 (2) | 0.0306 (15) | 0.0438 (19) | 0.0013 (14) | 0.0052 (16) | 0.0032 (13) |
C5 | 0.053 (2) | 0.0369 (16) | 0.0383 (19) | 0.0025 (15) | 0.0051 (17) | −0.0028 (14) |
C6 | 0.059 (3) | 0.085 (3) | 0.047 (2) | 0.008 (2) | −0.001 (2) | −0.002 (2) |
C7 | 0.066 (3) | 0.127 (4) | 0.069 (3) | 0.022 (3) | 0.017 (3) | 0.001 (3) |
C8 | 0.106 (4) | 0.097 (3) | 0.051 (3) | 0.027 (3) | 0.024 (3) | 0.002 (2) |
C9 | 0.094 (4) | 0.108 (4) | 0.046 (3) | 0.029 (3) | −0.010 (3) | −0.009 (2) |
C10 | 0.066 (3) | 0.081 (3) | 0.053 (3) | 0.019 (2) | −0.004 (2) | −0.014 (2) |
C11 | 0.040 (2) | 0.0418 (18) | 0.065 (2) | 0.0010 (16) | −0.0084 (19) | −0.0080 (17) |
C12 | 0.058 (3) | 0.057 (2) | 0.104 (3) | 0.014 (2) | −0.010 (3) | 0.000 (2) |
C13 | 0.055 (3) | 0.087 (4) | 0.158 (6) | 0.029 (3) | −0.005 (4) | −0.025 (4) |
C14 | 0.057 (3) | 0.120 (5) | 0.136 (5) | 0.009 (3) | 0.027 (3) | −0.045 (4) |
C15 | 0.063 (3) | 0.095 (3) | 0.101 (4) | −0.004 (3) | 0.024 (3) | −0.013 (3) |
C16 | 0.054 (2) | 0.057 (2) | 0.079 (3) | 0.0011 (19) | 0.010 (2) | −0.007 (2) |
C17 | 0.062 (3) | 0.055 (2) | 0.056 (2) | 0.000 (2) | −0.018 (2) | −0.0058 (18) |
C18 | 0.079 (4) | 0.076 (3) | 0.146 (5) | 0.009 (3) | −0.029 (3) | 0.017 (3) |
C19 | 0.071 (4) | 0.110 (5) | 0.185 (7) | 0.026 (3) | −0.026 (4) | 0.005 (4) |
C20 | 0.064 (4) | 0.119 (5) | 0.125 (5) | −0.004 (3) | −0.018 (3) | −0.024 (4) |
C21 | 0.067 (4) | 0.130 (5) | 0.166 (6) | −0.021 (4) | −0.005 (4) | 0.046 (4) |
C22 | 0.060 (3) | 0.102 (4) | 0.143 (5) | −0.004 (3) | −0.014 (3) | 0.043 (3) |
C23 | 0.060 (4) | 0.191 (7) | 0.210 (7) | −0.012 (4) | −0.013 (4) | −0.055 (6) |
C24 | 0.040 (2) | 0.058 (2) | 0.041 (2) | −0.0033 (17) | 0.0067 (16) | 0.0007 (16) |
C25 | 0.050 (2) | 0.068 (2) | 0.073 (3) | −0.003 (2) | −0.003 (2) | 0.010 (2) |
C26 | 0.069 (3) | 0.109 (4) | 0.077 (3) | −0.011 (3) | −0.024 (3) | 0.025 (3) |
C27 | 0.062 (3) | 0.150 (5) | 0.050 (3) | −0.026 (3) | −0.007 (2) | −0.010 (3) |
C28 | 0.052 (3) | 0.125 (4) | 0.077 (3) | −0.003 (3) | −0.001 (2) | −0.046 (3) |
C29 | 0.047 (2) | 0.085 (3) | 0.060 (2) | 0.004 (2) | 0.001 (2) | −0.023 (2) |
C30 | 0.043 (2) | 0.0534 (19) | 0.045 (2) | 0.0003 (16) | −0.0013 (17) | −0.0084 (16) |
C31 | 0.053 (3) | 0.096 (3) | 0.052 (2) | 0.015 (2) | 0.002 (2) | −0.007 (2) |
C32 | 0.054 (3) | 0.118 (4) | 0.073 (3) | 0.028 (3) | 0.002 (2) | −0.019 (3) |
C33 | 0.053 (3) | 0.086 (3) | 0.094 (4) | 0.024 (2) | −0.016 (3) | −0.012 (3) |
C34 | 0.059 (3) | 0.072 (3) | 0.071 (3) | 0.007 (2) | −0.014 (2) | 0.005 (2) |
C35 | 0.049 (2) | 0.058 (2) | 0.054 (2) | 0.0013 (18) | −0.0039 (19) | −0.0046 (18) |
C36 | 0.061 (2) | 0.051 (2) | 0.052 (2) | −0.0142 (19) | 0.010 (2) | −0.0005 (17) |
C37 | 0.112 (4) | 0.090 (3) | 0.100 (4) | −0.036 (3) | 0.053 (3) | −0.004 (3) |
C38 | 0.191 (6) | 0.083 (3) | 0.082 (3) | −0.062 (4) | −0.042 (4) | −0.001 (3) |
C39 | 0.105 (4) | 0.048 (2) | 0.165 (5) | −0.009 (3) | 0.031 (4) | −0.003 (3) |
N1 | 0.0481 (17) | 0.0426 (15) | 0.0433 (16) | 0.0055 (13) | −0.0089 (13) | −0.0003 (12) |
O1 | 0.0767 (18) | 0.0423 (12) | 0.0456 (14) | 0.0079 (12) | −0.0010 (13) | 0.0083 (10) |
O2 | 0.0413 (13) | 0.0470 (12) | 0.0404 (13) | −0.0055 (10) | 0.0103 (11) | −0.0046 (10) |
O3 | 0.101 (2) | 0.086 (2) | 0.0488 (16) | −0.0166 (17) | −0.0066 (15) | 0.0157 (14) |
O4 | 0.078 (2) | 0.0722 (18) | 0.0678 (17) | 0.0126 (15) | −0.0040 (15) | −0.0278 (14) |
S1 | 0.0541 (6) | 0.0333 (4) | 0.0456 (5) | 0.0001 (4) | 0.0063 (4) | 0.0002 (3) |
S2 | 0.0635 (6) | 0.0573 (5) | 0.0422 (5) | −0.0011 (5) | −0.0059 (5) | −0.0056 (4) |
Si1 | 0.0410 (5) | 0.0454 (5) | 0.0405 (5) | −0.0015 (4) | 0.0049 (4) | −0.0034 (4) |
Geometric parameters (Å, º) top
Br1—C2 | 1.961 (3) | C22—H22 | 0.9300 |
C1—N1 | 1.470 (4) | C23—H23A | 0.9600 |
C1—C11 | 1.505 (5) | C23—H23B | 0.9600 |
C1—C2 | 1.541 (4) | C23—H23C | 0.9600 |
C1—H1 | 0.9800 | C24—C29 | 1.386 (5) |
C2—C3 | 1.539 (4) | C24—C25 | 1.391 (5) |
C2—H2 | 0.9800 | C24—Si1 | 1.868 (3) |
C3—O2 | 1.419 (4) | C25—C26 | 1.386 (5) |
C3—C4 | 1.511 (4) | C25—H25 | 0.9300 |
C3—H3 | 0.9800 | C26—C27 | 1.362 (6) |
C4—S1 | 1.809 (3) | C26—H26 | 0.9300 |
C4—H4A | 0.9700 | C27—C28 | 1.348 (6) |
C4—H4B | 0.9700 | C27—H27 | 0.9300 |
C5—C6 | 1.368 (5) | C28—C29 | 1.389 (5) |
C5—C10 | 1.378 (5) | C28—H28 | 0.9300 |
C5—S1 | 1.788 (3) | C29—H29 | 0.9300 |
C6—C7 | 1.382 (5) | C30—C35 | 1.395 (5) |
C6—H6 | 0.9300 | C30—C31 | 1.392 (5) |
C7—C8 | 1.358 (6) | C30—Si1 | 1.866 (3) |
C7—H7 | 0.9300 | C31—C32 | 1.376 (5) |
C8—C9 | 1.367 (6) | C31—H31 | 0.9300 |
C8—H8 | 0.9300 | C32—C33 | 1.376 (6) |
C9—C10 | 1.376 (5) | C32—H32 | 0.9300 |
C9—H9 | 0.9300 | C33—C34 | 1.368 (6) |
C10—H10 | 0.9300 | C33—H33 | 0.9300 |
C11—C16 | 1.376 (5) | C34—C35 | 1.379 (5) |
C11—C12 | 1.382 (5) | C34—H34 | 0.9300 |
C12—C13 | 1.381 (6) | C35—H35 | 0.9300 |
C12—H12 | 0.9300 | C36—C37 | 1.513 (5) |
C13—C14 | 1.356 (7) | C36—C38 | 1.525 (5) |
C13—H13 | 0.9300 | C36—C39 | 1.527 (6) |
C14—C15 | 1.365 (7) | C36—Si1 | 1.886 (3) |
C14—H14 | 0.9300 | C37—H37A | 0.9600 |
C15—C16 | 1.378 (5) | C37—H37B | 0.9600 |
C15—H15 | 0.9300 | C37—H37C | 0.9600 |
C16—H16 | 0.9300 | C38—H38A | 0.9600 |
C17—C22 | 1.354 (6) | C38—H38B | 0.9600 |
C17—C18 | 1.358 (5) | C38—H38C | 0.9600 |
C17—S2 | 1.760 (4) | C39—H39A | 0.9600 |
C18—C19 | 1.395 (7) | C39—H39B | 0.9600 |
C18—H18 | 0.9300 | C39—H39C | 0.9600 |
C19—C20 | 1.337 (8) | N1—S2 | 1.607 (3) |
C19—H19 | 0.9300 | N1—H1A | 0.8600 |
C20—C21 | 1.335 (7) | O1—S1 | 1.498 (2) |
C20—C23 | 1.533 (7) | O2—Si1 | 1.662 (2) |
C21—C22 | 1.383 (6) | O3—S2 | 1.425 (3) |
C21—H21 | 0.9300 | O4—S2 | 1.431 (3) |
| | | |
N1—C1—C11 | 114.1 (3) | H23A—C23—H23C | 109.5 |
N1—C1—C2 | 108.5 (2) | H23B—C23—H23C | 109.5 |
C11—C1—C2 | 116.4 (3) | C29—C24—C25 | 116.0 (3) |
N1—C1—H1 | 105.6 | C29—C24—Si1 | 121.5 (3) |
C11—C1—H1 | 105.6 | C25—C24—Si1 | 122.5 (3) |
C2—C1—H1 | 105.6 | C26—C25—C24 | 122.3 (4) |
C3—C2—C1 | 114.3 (2) | C26—C25—H25 | 118.8 |
C3—C2—Br1 | 110.8 (2) | C24—C25—H25 | 118.8 |
C1—C2—Br1 | 112.7 (2) | C27—C26—C25 | 119.1 (4) |
C3—C2—H2 | 106.1 | C27—C26—H26 | 120.5 |
C1—C2—H2 | 106.1 | C25—C26—H26 | 120.5 |
Br1—C2—H2 | 106.1 | C28—C27—C26 | 121.0 (4) |
O2—C3—C4 | 107.1 (2) | C28—C27—H27 | 119.5 |
O2—C3—C2 | 110.5 (2) | C26—C27—H27 | 119.5 |
C4—C3—C2 | 114.6 (2) | C27—C28—C29 | 119.9 (4) |
O2—C3—H3 | 108.1 | C27—C28—H28 | 120.1 |
C4—C3—H3 | 108.1 | C29—C28—H28 | 120.1 |
C2—C3—H3 | 108.1 | C24—C29—C28 | 121.8 (4) |
C3—C4—S1 | 109.7 (2) | C24—C29—H29 | 119.1 |
C3—C4—H4A | 109.7 | C28—C29—H29 | 119.1 |
S1—C4—H4A | 109.7 | C35—C30—C31 | 116.3 (3) |
C3—C4—H4B | 109.7 | C35—C30—Si1 | 121.7 (3) |
S1—C4—H4B | 109.7 | C31—C30—Si1 | 122.0 (3) |
H4A—C4—H4B | 108.2 | C32—C31—C30 | 122.2 (4) |
C6—C5—C10 | 120.5 (3) | C32—C31—H31 | 118.9 |
C6—C5—S1 | 120.4 (3) | C30—C31—H31 | 118.9 |
C10—C5—S1 | 119.0 (3) | C33—C32—C31 | 119.8 (4) |
C5—C6—C7 | 119.2 (4) | C33—C32—H32 | 120.1 |
C5—C6—H6 | 120.4 | C31—C32—H32 | 120.1 |
C7—C6—H6 | 120.4 | C34—C33—C32 | 119.7 (4) |
C8—C7—C6 | 120.5 (4) | C34—C33—H33 | 120.1 |
C8—C7—H7 | 119.7 | C32—C33—H33 | 120.1 |
C6—C7—H7 | 119.7 | C33—C34—C35 | 120.2 (4) |
C7—C8—C9 | 120.2 (4) | C33—C34—H34 | 119.9 |
C7—C8—H8 | 119.9 | C35—C34—H34 | 119.9 |
C9—C8—H8 | 119.9 | C34—C35—C30 | 121.8 (4) |
C8—C9—C10 | 120.2 (4) | C34—C35—H35 | 119.1 |
C8—C9—H9 | 119.9 | C30—C35—H35 | 119.1 |
C10—C9—H9 | 119.9 | C37—C36—C38 | 109.5 (4) |
C5—C10—C9 | 119.3 (4) | C37—C36—C39 | 107.8 (4) |
C5—C10—H10 | 120.3 | C38—C36—C39 | 108.2 (4) |
C9—C10—H10 | 120.3 | C37—C36—Si1 | 110.7 (3) |
C16—C11—C12 | 118.6 (4) | C38—C36—Si1 | 107.4 (3) |
C16—C11—C1 | 121.8 (3) | C39—C36—Si1 | 113.1 (3) |
C12—C11—C1 | 119.6 (3) | C36—C37—H37A | 109.5 |
C13—C12—C11 | 120.1 (4) | C36—C37—H37B | 109.5 |
C13—C12—H12 | 120.0 | H37A—C37—H37B | 109.5 |
C11—C12—H12 | 120.0 | C36—C37—H37C | 109.5 |
C14—C13—C12 | 120.7 (5) | H37A—C37—H37C | 109.5 |
C14—C13—H13 | 119.7 | H37B—C37—H37C | 109.5 |
C12—C13—H13 | 119.7 | C36—C38—H38A | 109.5 |
C13—C14—C15 | 119.8 (5) | C36—C38—H38B | 109.5 |
C13—C14—H14 | 120.1 | H38A—C38—H38B | 109.5 |
C15—C14—H14 | 120.1 | C36—C38—H38C | 109.5 |
C14—C15—C16 | 120.3 (5) | H38A—C38—H38C | 109.5 |
C14—C15—H15 | 119.8 | H38B—C38—H38C | 109.5 |
C16—C15—H15 | 119.8 | C36—C39—H39A | 109.5 |
C11—C16—C15 | 120.5 (4) | C36—C39—H39B | 109.5 |
C11—C16—H16 | 119.7 | H39A—C39—H39B | 109.5 |
C15—C16—H16 | 119.7 | C36—C39—H39C | 109.5 |
C22—C17—C18 | 118.2 (4) | H39A—C39—H39C | 109.5 |
C22—C17—S2 | 120.2 (3) | H39B—C39—H39C | 109.5 |
C18—C17—S2 | 121.5 (4) | C1—N1—S2 | 120.8 (2) |
C17—C18—C19 | 119.7 (5) | C1—N1—H1A | 119.6 |
C17—C18—H18 | 120.2 | S2—N1—H1A | 119.6 |
C19—C18—H18 | 120.2 | C3—O2—Si1 | 128.76 (19) |
C20—C19—C18 | 122.1 (5) | O1—S1—C5 | 106.63 (15) |
C20—C19—H19 | 118.9 | O1—S1—C4 | 104.99 (14) |
C18—C19—H19 | 118.9 | C5—S1—C4 | 96.58 (14) |
C19—C20—C21 | 117.4 (5) | O3—S2—O4 | 120.62 (18) |
C19—C20—C23 | 121.3 (6) | O3—S2—N1 | 107.36 (15) |
C21—C20—C23 | 121.3 (6) | O4—S2—N1 | 105.99 (15) |
C20—C21—C22 | 122.3 (5) | O3—S2—C17 | 106.75 (18) |
C20—C21—H21 | 118.8 | O4—S2—C17 | 106.74 (17) |
C22—C21—H21 | 118.8 | N1—S2—C17 | 109.02 (15) |
C17—C22—C21 | 120.2 (5) | O2—Si1—C30 | 106.84 (14) |
C17—C22—H22 | 119.9 | O2—Si1—C24 | 110.02 (13) |
C21—C22—H22 | 119.9 | C30—Si1—C24 | 109.21 (15) |
C20—C23—H23A | 109.5 | O2—Si1—C36 | 106.66 (14) |
C20—C23—H23B | 109.5 | C30—Si1—C36 | 109.06 (16) |
H23A—C23—H23B | 109.5 | C24—Si1—C36 | 114.75 (16) |
C20—C23—H23C | 109.5 | | |
| | | |
N1—C1—C2—C3 | −168.5 (2) | C30—C31—C32—C33 | 1.3 (7) |
C11—C1—C2—C3 | 61.1 (4) | C31—C32—C33—C34 | −1.1 (7) |
N1—C1—C2—Br1 | 63.8 (3) | C32—C33—C34—C35 | 0.4 (6) |
C11—C1—C2—Br1 | −66.5 (3) | C33—C34—C35—C30 | 0.1 (6) |
C1—C2—C3—O2 | 154.6 (3) | C31—C30—C35—C34 | 0.0 (5) |
Br1—C2—C3—O2 | −76.8 (3) | Si1—C30—C35—C34 | 176.9 (3) |
C1—C2—C3—C4 | −84.3 (3) | C11—C1—N1—S2 | −87.4 (3) |
Br1—C2—C3—C4 | 44.4 (3) | C2—C1—N1—S2 | 141.0 (2) |
O2—C3—C4—S1 | −69.0 (3) | C4—C3—O2—Si1 | 159.52 (19) |
C2—C3—C4—S1 | 168.1 (2) | C2—C3—O2—Si1 | −75.0 (3) |
C10—C5—C6—C7 | 1.0 (6) | C6—C5—S1—O1 | −11.1 (3) |
S1—C5—C6—C7 | 178.2 (3) | C10—C5—S1—O1 | 166.2 (3) |
C5—C6—C7—C8 | 0.2 (7) | C6—C5—S1—C4 | 96.8 (3) |
C6—C7—C8—C9 | −0.5 (7) | C10—C5—S1—C4 | −86.0 (3) |
C7—C8—C9—C10 | −0.6 (7) | C3—C4—S1—O1 | −64.9 (2) |
C6—C5—C10—C9 | −2.0 (5) | C3—C4—S1—C5 | −174.1 (2) |
S1—C5—C10—C9 | −179.3 (3) | C1—N1—S2—O3 | −36.6 (3) |
C8—C9—C10—C5 | 1.8 (6) | C1—N1—S2—O4 | −166.8 (3) |
N1—C1—C11—C16 | −46.2 (4) | C1—N1—S2—C17 | 78.6 (3) |
C2—C1—C11—C16 | 81.5 (4) | C22—C17—S2—O3 | −170.0 (4) |
N1—C1—C11—C12 | 135.1 (3) | C18—C17—S2—O3 | 7.7 (4) |
C2—C1—C11—C12 | −97.2 (4) | C22—C17—S2—O4 | −39.8 (4) |
C16—C11—C12—C13 | −1.1 (6) | C18—C17—S2—O4 | 137.9 (4) |
C1—C11—C12—C13 | 177.6 (4) | C22—C17—S2—N1 | 74.3 (4) |
C11—C12—C13—C14 | 0.4 (7) | C18—C17—S2—N1 | −108.0 (4) |
C12—C13—C14—C15 | 0.3 (8) | C3—O2—Si1—C30 | 122.7 (2) |
C13—C14—C15—C16 | −0.4 (8) | C3—O2—Si1—C24 | 4.3 (3) |
C12—C11—C16—C15 | 1.1 (6) | C3—O2—Si1—C36 | −120.7 (2) |
C1—C11—C16—C15 | −177.6 (3) | C35—C30—Si1—O2 | 13.0 (3) |
C14—C15—C16—C11 | −0.3 (7) | C31—C30—Si1—O2 | −170.3 (3) |
C22—C17—C18—C19 | 1.4 (8) | C35—C30—Si1—C24 | 132.0 (3) |
S2—C17—C18—C19 | −176.3 (4) | C31—C30—Si1—C24 | −51.3 (3) |
C17—C18—C19—C20 | −2.3 (10) | C35—C30—Si1—C36 | −101.9 (3) |
C18—C19—C20—C21 | 1.3 (10) | C31—C30—Si1—C36 | 74.8 (3) |
C18—C19—C20—C23 | −179.2 (5) | C29—C24—Si1—O2 | 105.0 (3) |
C19—C20—C21—C22 | 0.4 (10) | C25—C24—Si1—O2 | −73.0 (3) |
C23—C20—C21—C22 | −179.1 (6) | C29—C24—Si1—C30 | −11.9 (3) |
C18—C17—C22—C21 | 0.3 (8) | C25—C24—Si1—C30 | 170.1 (3) |
S2—C17—C22—C21 | 178.0 (4) | C29—C24—Si1—C36 | −134.7 (3) |
C20—C21—C22—C17 | −1.2 (10) | C25—C24—Si1—C36 | 47.3 (3) |
C29—C24—C25—C26 | 1.6 (5) | C37—C36—Si1—O2 | −177.0 (3) |
Si1—C24—C25—C26 | 179.6 (3) | C38—C36—Si1—O2 | −57.5 (4) |
C24—C25—C26—C27 | −0.2 (7) | C39—C36—Si1—O2 | 61.9 (3) |
C25—C26—C27—C28 | −1.3 (7) | C37—C36—Si1—C30 | −62.0 (3) |
C26—C27—C28—C29 | 1.4 (7) | C38—C36—Si1—C30 | 57.6 (4) |
C25—C24—C29—C28 | −1.5 (6) | C39—C36—Si1—C30 | 177.0 (3) |
Si1—C24—C29—C28 | −179.6 (3) | C37—C36—Si1—C24 | 60.9 (4) |
C27—C28—C29—C24 | 0.1 (7) | C38—C36—Si1—C24 | −179.6 (3) |
C35—C30—C31—C32 | −0.7 (6) | C39—C36—Si1—C24 | −60.2 (3) |
Si1—C30—C31—C32 | −177.6 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Br1 | 0.86 | 2.87 | 3.261 (2) | 110 |
C1—H1···O3 | 0.98 | 2.38 | 2.906 (4) | 113 |
C4—H4B···Br1 | 0.97 | 2.81 | 3.140 (3) | 101 |
C6—H6···O1 | 0.93 | 2.54 | 2.931 (4) | 106 |
C18—H18···O3 | 0.93 | 2.53 | 2.893 (6) | 104 |
N1—H1A···O1i | 0.86 | 2.19 | 2.883 (3) | 137 |
C25—H25···O4ii | 0.93 | 2.55 | 3.271 (5) | 135 |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z. |