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The structure of the title compound, C
46H
41N
3O
6S
4, is stabilized by C—H
O, C—H
S and C—H
N interactions, and the packing of the molecules is stabilized by several C—H
π interactions, and face-to-face and edge-to-face π–π interactions.
Supporting information
CCDC reference: 287458
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- Disorder in main residue
- R factor = 0.074
- wR factor = 0.207
- Data-to-parameter ratio = 19.7
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT241_ALERT_2_A Check High Ueq as Compared to Neighbors for C49
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.63 Ratio
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for O6A
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) ..... 10 Ang.
PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) ..... 10 Ang.
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S2
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S4
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C34
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O6B
PLAT301_ALERT_3_C Main Residue Disorder ......................... 2.00 Perc.
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........ O6B
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... CGA
PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... CGB
PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... CGC
PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... CGD
PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... CGH
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C46 H38 N3 O6 S4
Atom count from _chemical_formula_moiety:C46 H41 N3 O6 S4
1 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
20 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
9 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
4 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
To a solution of aminoacetaldehyde dimethyl acetal (4.4 ml, 40 mmol) in chloroform (40 ml) was added a solution of 1-phenylsulfonyl-2-bromomethyl-3-phenylthioindole (10 mmol) in chloroform (15 ml) and the mixture was stirred at room temperature for 4 h. Work-up of the reaction and crystallization of the residue in methanol afforded the title compound (yield 4.1 g, 85%) as the sole product.
All the H atoms were fixed geometrically and allowed to ride on their parent atoms [C—H = 0.93–0.98 Å, and Uiso(H) = 1.2Ueq(C) and 1.5Ueq(Cmethyl)]. Atom O6 is found to be disordered and the site occupancy factor of the major and minor conformations were refined, with their sum constrained to unity [O6A/O6B 0.561 (11):0.439 (11)].
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
{
N,
N-Bis[3-(phenylysulfanyl)-1-(phenylsulfonyl)indol-2- ylmethyl]amino}acetaldehyde dimethyl acetal
top
Crystal data top
C46H41N3O6S4 | F(000) = 1788 |
Mr = 857.03 | Dx = 1.318 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.7146 (1) Å | Cell parameters from 8042 reflections |
b = 23.8939 (1) Å | θ = 1.5–28.5° |
c = 16.8782 (3) Å | µ = 0.27 mm−1 |
β = 91.846 (1)° | T = 293 K |
V = 4318.81 (9) Å3 | Block, colourless |
Z = 4 | 0.40 × 0.36 × 0.28 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 5223 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.066 |
Graphite monochromator | θmax = 28.5°, θmin = 1.5° |
ω scans | h = −14→12 |
29148 measured reflections | k = −31→30 |
10689 independent reflections | l = −15→22 |
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)] = 0.074 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.207 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0814P)2 + 1.9503P] where P = (Fo2 + 2Fc2)/3 |
10689 reflections | (Δ/σ)max < 0.001 |
543 parameters | Δρmax = 0.56 e Å−3 |
4 restraints | Δρmin = −0.45 e Å−3 |
Crystal data top
C46H41N3O6S4 | V = 4318.81 (9) Å3 |
Mr = 857.03 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.7146 (1) Å | µ = 0.27 mm−1 |
b = 23.8939 (1) Å | T = 293 K |
c = 16.8782 (3) Å | 0.40 × 0.36 × 0.28 mm |
β = 91.846 (1)° | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 5223 reflections with I > 2σ(I) |
29148 measured reflections | Rint = 0.066 |
10689 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.074 | 4 restraints |
wR(F2) = 0.207 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.56 e Å−3 |
10689 reflections | Δρmin = −0.45 e Å−3 |
543 parameters | |
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 | Occ. (<1) |
S1 | 0.03094 (9) | 0.12078 (4) | 0.13018 (6) | 0.0519 (3) | |
S2 | −0.18950 (12) | 0.19653 (5) | 0.40502 (7) | 0.0763 (4) | |
O1 | 0.0408 (3) | 0.15635 (12) | 0.06275 (16) | 0.0704 (8) | |
O2 | 0.1399 (2) | 0.10436 (11) | 0.17259 (15) | 0.0606 (7) | |
N1 | −0.0581 (3) | 0.15581 (12) | 0.19493 (17) | 0.0459 (7) | |
C2 | −0.0559 (3) | 0.15283 (14) | 0.2791 (2) | 0.0460 (8) | |
C3 | −0.1495 (4) | 0.18668 (15) | 0.3059 (2) | 0.0542 (10) | |
C4 | −0.2142 (3) | 0.21075 (15) | 0.2391 (2) | 0.0518 (9) | |
C5 | −0.1577 (3) | 0.19132 (14) | 0.1704 (2) | 0.0485 (9) | |
C6 | −0.2015 (4) | 0.20612 (16) | 0.0951 (3) | 0.0636 (11) | |
H6 | −0.1645 | 0.1929 | 0.0497 | 0.076* | |
C7 | −0.3021 (4) | 0.24121 (18) | 0.0914 (3) | 0.0773 (14) | |
H7 | −0.3334 | 0.2525 | 0.0419 | 0.093* | |
C8 | −0.3600 (4) | 0.26087 (19) | 0.1593 (4) | 0.0800 (14) | |
H8 | −0.4287 | 0.2845 | 0.1537 | 0.096* | |
C9 | −0.3179 (4) | 0.24626 (17) | 0.2332 (3) | 0.0707 (12) | |
H9 | −0.3565 | 0.2594 | 0.2781 | 0.085* | |
C10 | −0.0550 (3) | 0.06121 (16) | 0.1031 (2) | 0.0487 (9) | |
C11 | −0.1143 (4) | 0.05786 (19) | 0.0297 (2) | 0.0600 (10) | |
H11 | −0.1152 | 0.0883 | −0.0047 | 0.072* | |
C12 | −0.1726 (4) | 0.0084 (2) | 0.0084 (3) | 0.0732 (13) | |
H12 | −0.2129 | 0.0054 | −0.0411 | 0.088* | |
C13 | −0.1717 (4) | −0.03645 (19) | 0.0592 (3) | 0.0670 (12) | |
H13 | −0.2106 | −0.0697 | 0.0438 | 0.080* | |
C14 | −0.1146 (4) | −0.03243 (18) | 0.1315 (3) | 0.0693 (12) | |
H14 | −0.1156 | −0.0628 | 0.1659 | 0.083* | |
C15 | −0.0547 (4) | 0.01622 (16) | 0.1547 (2) | 0.0575 (10) | |
H15 | −0.0147 | 0.0188 | 0.2043 | 0.069* | |
C16 | −0.1135 (4) | 0.25987 (17) | 0.4320 (2) | 0.0644 (11) | |
C17 | −0.0037 (5) | 0.2780 (2) | 0.3980 (3) | 0.0780 (13) | |
H17 | 0.0305 | 0.2577 | 0.3570 | 0.094* | |
C18 | 0.0541 (6) | 0.3262 (3) | 0.4254 (3) | 0.1011 (18) | |
H18 | 0.1279 | 0.3382 | 0.4035 | 0.121* | |
C19 | 0.0020 (9) | 0.3562 (3) | 0.4853 (4) | 0.119 (2) | |
H19 | 0.0405 | 0.3889 | 0.5031 | 0.143* | |
C20 | −0.1057 (8) | 0.3388 (3) | 0.5191 (4) | 0.119 (2) | |
H20 | −0.1382 | 0.3591 | 0.5607 | 0.143* | |
C21 | −0.1665 (5) | 0.2910 (2) | 0.4919 (3) | 0.0902 (16) | |
H21 | −0.2415 | 0.2800 | 0.5133 | 0.108* | |
C22 | 0.0393 (3) | 0.12299 (14) | 0.3287 (2) | 0.0489 (9) | |
H22A | 0.1205 | 0.1299 | 0.3069 | 0.059* | |
H22B | 0.0401 | 0.1392 | 0.3814 | 0.059* | |
N23 | 0.0229 (3) | 0.06191 (11) | 0.33627 (17) | 0.0468 (7) | |
C46 | −0.0882 (4) | 0.04992 (17) | 0.3836 (3) | 0.0697 (12) | |
H46A | −0.1529 | 0.0766 | 0.3685 | 0.084* | |
H46B | −0.0660 | 0.0565 | 0.4390 | 0.084* | |
S3 | 0.22991 (8) | −0.05614 (4) | 0.24818 (6) | 0.0475 (2) | |
S4 | 0.35781 (12) | 0.13191 (5) | 0.41117 (7) | 0.0744 (4) | |
O3 | 0.2462 (3) | −0.06861 (11) | 0.16620 (15) | 0.0618 (7) | |
O4 | 0.1103 (2) | −0.06092 (10) | 0.28230 (16) | 0.0570 (7) | |
N25 | 0.2763 (3) | 0.00993 (11) | 0.26098 (18) | 0.0486 (7) | |
C26 | 0.2513 (3) | 0.04376 (14) | 0.3282 (2) | 0.0453 (8) | |
C27 | 0.3448 (3) | 0.08208 (15) | 0.3358 (2) | 0.0547 (10) | |
C28 | 0.4339 (4) | 0.07319 (16) | 0.2742 (3) | 0.0586 (10) | |
C29 | 0.3905 (3) | 0.02902 (15) | 0.2280 (3) | 0.0561 (10) | |
C30 | 0.4548 (4) | 0.00988 (19) | 0.1624 (3) | 0.0737 (13) | |
H30 | 0.4249 | −0.0198 | 0.1317 | 0.088* | |
C31 | 0.5658 (5) | 0.0372 (2) | 0.1452 (4) | 0.0967 (19) | |
H31 | 0.6115 | 0.0252 | 0.1024 | 0.116* | |
C32 | 0.6093 (5) | 0.0820 (2) | 0.1904 (4) | 0.0970 (18) | |
H32 | 0.6832 | 0.0997 | 0.1774 | 0.116* | |
C33 | 0.5451 (4) | 0.10017 (19) | 0.2537 (3) | 0.0807 (15) | |
H33 | 0.5746 | 0.1305 | 0.2833 | 0.097* | |
C34 | 0.3360 (3) | −0.09629 (14) | 0.3041 (2) | 0.0500 (9) | |
C35 | 0.4387 (4) | −0.11872 (19) | 0.2684 (3) | 0.0762 (13) | |
H35 | 0.4524 | −0.1114 | 0.2153 | 0.091* | |
C36 | 0.5205 (5) | −0.1518 (2) | 0.3115 (3) | 0.1027 (19) | |
H36 | 0.5893 | −0.1675 | 0.2878 | 0.123* | |
C37 | 0.4997 (6) | −0.1614 (2) | 0.3894 (4) | 0.1038 (19) | |
H37 | 0.5550 | −0.1838 | 0.4187 | 0.125* | |
C38 | 0.3983 (5) | −0.1385 (2) | 0.4256 (3) | 0.0983 (17) | |
H38 | 0.3861 | −0.1454 | 0.4790 | 0.118* | |
C39 | 0.3158 (4) | −0.1057 (2) | 0.3833 (3) | 0.0742 (13) | |
H39 | 0.2473 | −0.0901 | 0.4075 | 0.089* | |
C40 | 0.3675 (4) | 0.19614 (16) | 0.3591 (3) | 0.0587 (10) | |
C41 | 0.3227 (4) | 0.20433 (18) | 0.2826 (3) | 0.0674 (12) | |
H41 | 0.2875 | 0.1747 | 0.2541 | 0.081* | |
C42 | 0.3300 (4) | 0.2566 (2) | 0.2484 (3) | 0.0850 (15) | |
H42 | 0.2997 | 0.2622 | 0.1968 | 0.102* | |
C43 | 0.3826 (6) | 0.3005 (2) | 0.2911 (5) | 0.100 (2) | |
H43 | 0.3876 | 0.3358 | 0.2681 | 0.120* | |
C44 | 0.4271 (6) | 0.2921 (2) | 0.3667 (4) | 0.0974 (18) | |
H44 | 0.4627 | 0.3218 | 0.3950 | 0.117* | |
C45 | 0.4197 (4) | 0.24078 (18) | 0.4010 (3) | 0.0769 (13) | |
H45 | 0.4499 | 0.2356 | 0.4527 | 0.092* | |
C24 | 0.1356 (3) | 0.03938 (15) | 0.3768 (2) | 0.0506 (9) | |
H24A | 0.1215 | 0.0004 | 0.3896 | 0.061* | |
H24B | 0.1499 | 0.0594 | 0.4262 | 0.061* | |
C47 | −0.1432 (4) | −0.0087 (2) | 0.3762 (3) | 0.0951 (18) | |
H47 | −0.1674 | −0.0212 | 0.3226 | 0.114* | |
C49 | −0.3618 (5) | 0.0004 (4) | 0.4082 (5) | 0.165 (3) | |
O6A | −0.2349 (5) | −0.0104 (3) | 0.4316 (3) | 0.097 (3) | 0.561 (11) |
O6B | −0.2672 (5) | −0.0177 (3) | 0.3562 (5) | 0.107 (5) | 0.439 (11) |
O5 | −0.0696 (4) | −0.04492 (13) | 0.42085 (19) | 0.0891 (10) | |
C48 | −0.0968 (6) | −0.1033 (2) | 0.4066 (4) | 0.108 (2) | |
H48A | −0.1754 | −0.1126 | 0.4290 | 0.163* | |
H48B | −0.0320 | −0.1259 | 0.4308 | 0.163* | |
H48C | −0.1011 | −0.1102 | 0.3506 | 0.163* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0467 (5) | 0.0590 (6) | 0.0506 (6) | 0.0006 (4) | 0.0100 (4) | 0.0039 (5) |
S2 | 0.0897 (9) | 0.0701 (8) | 0.0712 (8) | 0.0003 (6) | 0.0356 (7) | −0.0031 (6) |
O1 | 0.0751 (19) | 0.080 (2) | 0.0567 (17) | −0.0003 (16) | 0.0165 (14) | 0.0183 (15) |
O2 | 0.0406 (14) | 0.0768 (19) | 0.0645 (18) | 0.0034 (13) | 0.0034 (12) | −0.0032 (14) |
N1 | 0.0463 (17) | 0.0418 (16) | 0.0500 (18) | 0.0022 (13) | 0.0061 (14) | 0.0009 (13) |
C2 | 0.046 (2) | 0.042 (2) | 0.050 (2) | −0.0057 (16) | 0.0077 (17) | 0.0054 (16) |
C3 | 0.052 (2) | 0.046 (2) | 0.065 (3) | 0.0001 (18) | 0.0121 (19) | −0.0013 (19) |
C4 | 0.044 (2) | 0.040 (2) | 0.072 (3) | −0.0030 (16) | 0.0092 (19) | 0.0033 (18) |
C5 | 0.043 (2) | 0.0379 (19) | 0.065 (3) | −0.0057 (16) | 0.0023 (18) | 0.0049 (17) |
C6 | 0.074 (3) | 0.046 (2) | 0.070 (3) | −0.001 (2) | −0.005 (2) | 0.007 (2) |
C7 | 0.074 (3) | 0.056 (3) | 0.100 (4) | 0.002 (2) | −0.024 (3) | 0.018 (3) |
C8 | 0.062 (3) | 0.055 (3) | 0.122 (5) | 0.010 (2) | −0.005 (3) | 0.019 (3) |
C9 | 0.057 (3) | 0.050 (2) | 0.106 (4) | 0.008 (2) | 0.018 (3) | 0.004 (2) |
C10 | 0.043 (2) | 0.057 (2) | 0.046 (2) | 0.0081 (17) | 0.0050 (16) | −0.0071 (18) |
C11 | 0.055 (2) | 0.073 (3) | 0.052 (2) | 0.014 (2) | 0.0032 (19) | −0.001 (2) |
C12 | 0.062 (3) | 0.100 (4) | 0.057 (3) | 0.011 (3) | −0.007 (2) | −0.019 (3) |
C13 | 0.064 (3) | 0.066 (3) | 0.070 (3) | 0.000 (2) | 0.002 (2) | −0.018 (2) |
C14 | 0.078 (3) | 0.055 (3) | 0.074 (3) | 0.000 (2) | −0.010 (2) | −0.002 (2) |
C15 | 0.064 (3) | 0.055 (2) | 0.053 (2) | 0.0082 (19) | −0.005 (2) | −0.0053 (19) |
C16 | 0.075 (3) | 0.062 (3) | 0.056 (3) | 0.018 (2) | 0.006 (2) | 0.001 (2) |
C17 | 0.100 (4) | 0.072 (3) | 0.062 (3) | −0.001 (3) | 0.002 (3) | 0.000 (2) |
C18 | 0.130 (5) | 0.092 (4) | 0.080 (4) | −0.020 (4) | −0.020 (4) | 0.007 (3) |
C19 | 0.195 (8) | 0.070 (4) | 0.090 (5) | −0.001 (5) | −0.037 (5) | −0.006 (3) |
C20 | 0.179 (7) | 0.093 (5) | 0.083 (4) | 0.044 (5) | −0.011 (5) | −0.030 (4) |
C21 | 0.109 (4) | 0.087 (4) | 0.076 (3) | 0.024 (3) | 0.014 (3) | −0.019 (3) |
C22 | 0.053 (2) | 0.043 (2) | 0.052 (2) | −0.0039 (16) | 0.0031 (17) | 0.0005 (16) |
N23 | 0.0475 (17) | 0.0408 (17) | 0.0525 (18) | −0.0019 (13) | 0.0087 (14) | 0.0072 (13) |
C46 | 0.067 (3) | 0.062 (3) | 0.082 (3) | −0.002 (2) | 0.025 (2) | 0.012 (2) |
S3 | 0.0482 (5) | 0.0395 (5) | 0.0545 (6) | 0.0017 (4) | −0.0036 (4) | 0.0030 (4) |
S4 | 0.0992 (9) | 0.0587 (7) | 0.0638 (7) | −0.0232 (6) | −0.0233 (6) | 0.0077 (5) |
O3 | 0.0782 (19) | 0.0551 (16) | 0.0513 (16) | 0.0067 (14) | −0.0087 (13) | −0.0023 (12) |
O4 | 0.0484 (15) | 0.0489 (15) | 0.0736 (18) | −0.0038 (12) | 0.0013 (13) | 0.0014 (13) |
N25 | 0.0479 (17) | 0.0388 (16) | 0.059 (2) | −0.0038 (13) | 0.0065 (15) | 0.0052 (14) |
C26 | 0.049 (2) | 0.0400 (19) | 0.047 (2) | 0.0003 (16) | −0.0046 (17) | 0.0068 (16) |
C27 | 0.055 (2) | 0.043 (2) | 0.065 (3) | −0.0056 (18) | −0.012 (2) | 0.0095 (18) |
C28 | 0.048 (2) | 0.045 (2) | 0.082 (3) | −0.0039 (17) | −0.004 (2) | 0.017 (2) |
C29 | 0.048 (2) | 0.043 (2) | 0.078 (3) | 0.0060 (17) | 0.009 (2) | 0.0157 (19) |
C30 | 0.071 (3) | 0.057 (3) | 0.094 (4) | 0.012 (2) | 0.022 (3) | 0.013 (2) |
C31 | 0.078 (3) | 0.076 (4) | 0.140 (5) | 0.015 (3) | 0.058 (3) | 0.030 (3) |
C32 | 0.061 (3) | 0.076 (4) | 0.156 (6) | −0.002 (3) | 0.037 (3) | 0.032 (4) |
C33 | 0.050 (3) | 0.062 (3) | 0.130 (5) | −0.006 (2) | 0.002 (3) | 0.024 (3) |
C34 | 0.055 (2) | 0.0387 (19) | 0.056 (2) | 0.0033 (17) | −0.0037 (18) | 0.0039 (17) |
C35 | 0.091 (3) | 0.080 (3) | 0.057 (3) | 0.037 (3) | −0.004 (2) | 0.001 (2) |
C36 | 0.105 (4) | 0.114 (4) | 0.088 (4) | 0.064 (4) | −0.006 (3) | 0.002 (3) |
C37 | 0.110 (4) | 0.113 (5) | 0.086 (4) | 0.053 (4) | −0.017 (3) | 0.023 (3) |
C38 | 0.108 (4) | 0.122 (5) | 0.065 (3) | 0.026 (4) | −0.006 (3) | 0.034 (3) |
C39 | 0.068 (3) | 0.087 (3) | 0.067 (3) | 0.015 (2) | 0.005 (2) | 0.022 (2) |
C40 | 0.058 (2) | 0.049 (2) | 0.068 (3) | −0.0013 (18) | 0.000 (2) | 0.003 (2) |
C41 | 0.057 (2) | 0.058 (3) | 0.087 (3) | −0.004 (2) | −0.002 (2) | 0.016 (2) |
C42 | 0.071 (3) | 0.082 (4) | 0.102 (4) | 0.018 (3) | 0.008 (3) | 0.036 (3) |
C43 | 0.107 (4) | 0.041 (3) | 0.155 (6) | 0.020 (3) | 0.051 (4) | 0.017 (3) |
C44 | 0.126 (5) | 0.045 (3) | 0.123 (5) | 0.002 (3) | 0.036 (4) | −0.018 (3) |
C45 | 0.094 (3) | 0.053 (3) | 0.084 (3) | −0.004 (2) | 0.013 (3) | −0.013 (2) |
C24 | 0.064 (2) | 0.039 (2) | 0.049 (2) | −0.0059 (17) | −0.0015 (18) | 0.0044 (16) |
C47 | 0.064 (3) | 0.082 (4) | 0.141 (5) | −0.023 (3) | 0.013 (3) | 0.045 (3) |
C49 | 0.105 (6) | 0.175 (8) | 0.216 (9) | 0.013 (5) | 0.028 (6) | 0.047 (7) |
O6A | 0.077 (5) | 0.139 (6) | 0.076 (5) | −0.038 (4) | 0.004 (3) | 0.039 (4) |
O6B | 0.087 (7) | 0.094 (6) | 0.138 (10) | −0.027 (5) | −0.023 (6) | 0.038 (6) |
O5 | 0.132 (3) | 0.059 (2) | 0.077 (2) | −0.0175 (19) | 0.016 (2) | −0.0035 (16) |
C48 | 0.145 (5) | 0.057 (3) | 0.126 (5) | −0.031 (3) | 0.038 (4) | −0.011 (3) |
Geometric parameters (Å, º) top
S1—O2 | 1.406 (3) | S3—N25 | 1.667 (3) |
S1—O1 | 1.427 (3) | S3—C34 | 1.742 (4) |
S1—N1 | 1.695 (3) | S4—C27 | 1.744 (4) |
S1—C10 | 1.748 (4) | S4—C40 | 1.773 (4) |
S2—C3 | 1.757 (4) | N25—C26 | 1.425 (4) |
S2—C16 | 1.771 (5) | N25—C29 | 1.435 (4) |
N1—C5 | 1.415 (4) | C26—C27 | 1.360 (5) |
N1—C2 | 1.421 (4) | C26—C24 | 1.511 (5) |
C2—C3 | 1.376 (5) | C27—C28 | 1.450 (5) |
C2—C22 | 1.482 (5) | C28—C29 | 1.384 (6) |
C3—C4 | 1.425 (5) | C28—C33 | 1.408 (5) |
C4—C9 | 1.399 (5) | C29—C30 | 1.400 (6) |
C4—C5 | 1.405 (5) | C30—C31 | 1.396 (6) |
C5—C6 | 1.386 (5) | C30—H30 | 0.9300 |
C6—C7 | 1.365 (6) | C31—C32 | 1.385 (8) |
C6—H6 | 0.9300 | C31—H31 | 0.9300 |
C7—C8 | 1.403 (7) | C32—C33 | 1.361 (7) |
C7—H7 | 0.9300 | C32—H32 | 0.9300 |
C8—C9 | 1.357 (6) | C33—H33 | 0.9300 |
C8—H8 | 0.9300 | C34—C35 | 1.380 (5) |
C9—H9 | 0.9300 | C34—C39 | 1.380 (5) |
C10—C11 | 1.376 (5) | C35—C36 | 1.372 (6) |
C10—C15 | 1.384 (5) | C35—H35 | 0.9300 |
C11—C12 | 1.379 (6) | C36—C37 | 1.359 (7) |
C11—H11 | 0.9300 | C36—H36 | 0.9300 |
C12—C13 | 1.372 (6) | C37—C38 | 1.377 (7) |
C12—H12 | 0.9300 | C37—H37 | 0.9300 |
C13—C14 | 1.351 (6) | C38—C39 | 1.365 (6) |
C13—H13 | 0.9300 | C38—H38 | 0.9300 |
C14—C15 | 1.379 (5) | C39—H39 | 0.9300 |
C14—H14 | 0.9300 | C40—C41 | 1.377 (6) |
C15—H15 | 0.9300 | C40—C45 | 1.387 (6) |
C16—C21 | 1.392 (6) | C41—C42 | 1.378 (6) |
C16—C17 | 1.394 (6) | C41—H41 | 0.9300 |
C17—C18 | 1.380 (7) | C42—C43 | 1.383 (8) |
C17—H17 | 0.9300 | C42—H42 | 0.9300 |
C18—C19 | 1.371 (8) | C43—C44 | 1.362 (8) |
C18—H18 | 0.9300 | C43—H43 | 0.9300 |
C19—C20 | 1.369 (9) | C44—C45 | 1.360 (7) |
C19—H19 | 0.9300 | C44—H44 | 0.9300 |
C20—C21 | 1.384 (8) | C45—H45 | 0.9300 |
C20—H20 | 0.9300 | C24—H24A | 0.9700 |
C21—H21 | 0.9300 | C24—H24B | 0.9700 |
C22—N23 | 1.476 (4) | C47—O5 | 1.378 (6) |
C22—H22A | 0.9700 | C47—O6B | 1.3779 (10) |
C22—H22B | 0.9700 | C47—O6A | 1.3784 (10) |
N23—C24 | 1.471 (4) | C47—H47 | 0.9800 |
N23—C46 | 1.483 (5) | C49—O6A | 1.4277 (10) |
C46—C47 | 1.524 (6) | C49—O6B | 1.4292 (10) |
C46—H46A | 0.9700 | O5—C48 | 1.443 (5) |
C46—H46B | 0.9700 | C48—H48A | 0.9600 |
S3—O4 | 1.426 (3) | C48—H48B | 0.9600 |
S3—O3 | 1.432 (3) | C48—H48C | 0.9600 |
| | | |
O2—S1—O1 | 119.39 (17) | C27—S4—C40 | 103.55 (19) |
O2—S1—N1 | 106.56 (15) | C26—N25—C29 | 108.2 (3) |
O1—S1—N1 | 106.12 (16) | C26—N25—S3 | 125.3 (2) |
O2—S1—C10 | 109.14 (17) | C29—N25—S3 | 120.3 (2) |
O1—S1—C10 | 109.16 (18) | C27—C26—N25 | 107.5 (3) |
N1—S1—C10 | 105.56 (15) | C27—C26—C24 | 127.5 (3) |
C3—S2—C16 | 103.58 (19) | N25—C26—C24 | 124.8 (3) |
C5—N1—C2 | 108.1 (3) | C26—C27—C28 | 109.5 (3) |
C5—N1—S1 | 122.8 (2) | C26—C27—S4 | 124.8 (3) |
C2—N1—S1 | 128.9 (2) | C28—C27—S4 | 125.7 (3) |
C3—C2—N1 | 108.1 (3) | C29—C28—C33 | 118.8 (4) |
C3—C2—C22 | 126.3 (3) | C29—C28—C27 | 107.4 (3) |
N1—C2—C22 | 125.3 (3) | C33—C28—C27 | 133.8 (4) |
C2—C3—C4 | 108.6 (3) | C28—C29—C30 | 122.0 (4) |
C2—C3—S2 | 126.5 (3) | C28—C29—N25 | 107.4 (3) |
C4—C3—S2 | 124.9 (3) | C30—C29—N25 | 130.6 (4) |
C9—C4—C5 | 120.2 (4) | C31—C30—C29 | 117.2 (5) |
C9—C4—C3 | 131.8 (4) | C31—C30—H30 | 121.4 |
C5—C4—C3 | 108.0 (3) | C29—C30—H30 | 121.4 |
C6—C5—C4 | 122.0 (4) | C32—C31—C30 | 121.3 (5) |
C6—C5—N1 | 130.7 (4) | C32—C31—H31 | 119.3 |
C4—C5—N1 | 107.2 (3) | C30—C31—H31 | 119.3 |
C7—C6—C5 | 116.3 (4) | C33—C32—C31 | 120.6 (4) |
C7—C6—H6 | 121.9 | C33—C32—H32 | 119.7 |
C5—C6—H6 | 121.9 | C31—C32—H32 | 119.7 |
C6—C7—C8 | 122.5 (4) | C32—C33—C28 | 120.0 (5) |
C6—C7—H7 | 118.8 | C32—C33—H33 | 120.0 |
C8—C7—H7 | 118.8 | C28—C33—H33 | 120.0 |
C9—C8—C7 | 121.5 (4) | C35—C34—C39 | 120.8 (4) |
C9—C8—H8 | 119.3 | C35—C34—S3 | 119.5 (3) |
C7—C8—H8 | 119.3 | C39—C34—S3 | 119.7 (3) |
C8—C9—C4 | 117.5 (4) | C36—C35—C34 | 119.8 (4) |
C8—C9—H9 | 121.3 | C36—C35—H35 | 120.1 |
C4—C9—H9 | 121.3 | C34—C35—H35 | 120.1 |
C11—C10—C15 | 120.9 (4) | C37—C36—C35 | 119.2 (5) |
C11—C10—S1 | 120.5 (3) | C37—C36—H36 | 120.4 |
C15—C10—S1 | 118.5 (3) | C35—C36—H36 | 120.4 |
C10—C11—C12 | 118.5 (4) | C36—C37—C38 | 121.2 (5) |
C10—C11—H11 | 120.8 | C36—C37—H37 | 119.4 |
C12—C11—H11 | 120.8 | C38—C37—H37 | 119.4 |
C13—C12—C11 | 120.8 (4) | C39—C38—C37 | 120.2 (5) |
C13—C12—H12 | 119.6 | C39—C38—H38 | 119.9 |
C11—C12—H12 | 119.6 | C37—C38—H38 | 119.9 |
C14—C13—C12 | 120.2 (4) | C38—C39—C34 | 118.7 (4) |
C14—C13—H13 | 119.9 | C38—C39—H39 | 120.6 |
C12—C13—H13 | 119.9 | C34—C39—H39 | 120.6 |
C13—C14—C15 | 120.7 (4) | C41—C40—C45 | 119.4 (4) |
C13—C14—H14 | 119.7 | C41—C40—S4 | 124.3 (3) |
C15—C14—H14 | 119.7 | C45—C40—S4 | 116.3 (3) |
C14—C15—C10 | 119.0 (4) | C42—C41—C40 | 119.9 (5) |
C14—C15—H15 | 120.5 | C42—C41—H41 | 120.1 |
C10—C15—H15 | 120.5 | C40—C41—H41 | 120.1 |
C21—C16—C17 | 120.2 (5) | C41—C42—C43 | 119.8 (5) |
C21—C16—S2 | 116.6 (4) | C41—C42—H42 | 120.1 |
C17—C16—S2 | 123.2 (3) | C43—C42—H42 | 120.1 |
C18—C17—C16 | 119.8 (5) | C44—C43—C42 | 120.1 (5) |
C18—C17—H17 | 120.1 | C44—C43—H43 | 120.0 |
C16—C17—H17 | 120.1 | C42—C43—H43 | 120.0 |
C19—C18—C17 | 119.6 (6) | C45—C44—C43 | 120.5 (5) |
C19—C18—H18 | 120.2 | C45—C44—H44 | 119.8 |
C17—C18—H18 | 120.2 | C43—C44—H44 | 119.8 |
C18—C19—C20 | 121.1 (6) | C44—C45—C40 | 120.3 (5) |
C18—C19—H19 | 119.5 | C44—C45—H45 | 119.8 |
C20—C19—H19 | 119.5 | C40—C45—H45 | 119.8 |
C19—C20—C21 | 120.4 (6) | N23—C24—C26 | 113.4 (3) |
C19—C20—H20 | 119.8 | N23—C24—H24A | 108.9 |
C21—C20—H20 | 119.8 | C26—C24—H24A | 108.9 |
C20—C21—C16 | 118.9 (6) | N23—C24—H24B | 108.9 |
C20—C21—H21 | 120.6 | C26—C24—H24B | 108.9 |
C16—C21—H21 | 120.6 | H24A—C24—H24B | 107.7 |
N23—C22—C2 | 116.3 (3) | O5—C47—O6B | 124.5 (5) |
N23—C22—H22A | 108.2 | O5—C47—O6A | 91.1 (4) |
C2—C22—H22A | 108.2 | O6B—C47—O6A | 57.2 (4) |
N23—C22—H22B | 108.2 | O5—C47—C46 | 108.6 (4) |
C2—C22—H22B | 108.2 | O6B—C47—C46 | 122.1 (5) |
H22A—C22—H22B | 107.4 | O6A—C47—C46 | 104.7 (4) |
C24—N23—C22 | 107.7 (3) | O5—C47—H47 | 116.4 |
C24—N23—C46 | 109.9 (3) | O6B—C47—H47 | 60.1 |
C22—N23—C46 | 109.7 (3) | O6A—C47—H47 | 116.4 |
N23—C46—C47 | 116.7 (3) | C46—C47—H47 | 116.4 |
N23—C46—H46A | 108.1 | O6A—C49—O6B | 55.0 (4) |
C47—C46—H46A | 108.1 | C47—O6A—C49 | 120.0 (4) |
N23—C46—H46B | 108.1 | C47—O6B—C49 | 120.0 (4) |
C47—C46—H46B | 108.1 | C47—O5—C48 | 114.0 (4) |
H46A—C46—H46B | 107.3 | O5—C48—H48A | 109.5 |
O4—S3—O3 | 120.82 (17) | O5—C48—H48B | 109.5 |
O4—S3—N25 | 106.94 (15) | H48A—C48—H48B | 109.5 |
O3—S3—N25 | 106.10 (16) | O5—C48—H48C | 109.5 |
O4—S3—C34 | 108.42 (17) | H48A—C48—H48C | 109.5 |
O3—S3—C34 | 108.16 (17) | H48B—C48—H48C | 109.5 |
N25—S3—C34 | 105.36 (16) | | |
| | | |
O2—S1—N1—C5 | 162.5 (3) | C29—N25—C26—C27 | 0.5 (4) |
O1—S1—N1—C5 | 34.3 (3) | S3—N25—C26—C27 | 152.7 (3) |
C10—S1—N1—C5 | −81.5 (3) | C29—N25—C26—C24 | 176.3 (3) |
O2—S1—N1—C2 | −22.6 (3) | S3—N25—C26—C24 | −31.6 (5) |
O1—S1—N1—C2 | −150.9 (3) | N25—C26—C27—C28 | −1.0 (4) |
C10—S1—N1—C2 | 93.3 (3) | C24—C26—C27—C28 | −176.6 (3) |
C5—N1—C2—C3 | −1.5 (4) | N25—C26—C27—S4 | −178.3 (3) |
S1—N1—C2—C3 | −176.9 (3) | C24—C26—C27—S4 | 6.1 (5) |
C5—N1—C2—C22 | −175.7 (3) | C40—S4—C27—C26 | −124.9 (3) |
S1—N1—C2—C22 | 8.8 (5) | C40—S4—C27—C28 | 58.2 (4) |
N1—C2—C3—C4 | 1.2 (4) | C26—C27—C28—C29 | 1.1 (4) |
C22—C2—C3—C4 | 175.4 (3) | S4—C27—C28—C29 | 178.4 (3) |
N1—C2—C3—S2 | 178.2 (3) | C26—C27—C28—C33 | 179.2 (4) |
C22—C2—C3—S2 | −7.6 (6) | S4—C27—C28—C33 | −3.6 (6) |
C16—S2—C3—C2 | 98.3 (4) | C33—C28—C29—C30 | 1.1 (6) |
C16—S2—C3—C4 | −85.1 (4) | C27—C28—C29—C30 | 179.5 (4) |
C2—C3—C4—C9 | 177.7 (4) | C33—C28—C29—N25 | −179.2 (3) |
S2—C3—C4—C9 | 0.5 (6) | C27—C28—C29—N25 | −0.8 (4) |
C2—C3—C4—C5 | −0.4 (4) | C26—N25—C29—C28 | 0.2 (4) |
S2—C3—C4—C5 | −177.6 (3) | S3—N25—C29—C28 | −153.6 (3) |
C9—C4—C5—C6 | −0.1 (5) | C26—N25—C29—C30 | 179.9 (4) |
C3—C4—C5—C6 | 178.3 (3) | S3—N25—C29—C30 | 26.2 (5) |
C9—C4—C5—N1 | −178.8 (3) | C28—C29—C30—C31 | 0.1 (6) |
C3—C4—C5—N1 | −0.5 (4) | N25—C29—C30—C31 | −179.6 (4) |
C2—N1—C5—C6 | −177.4 (4) | C29—C30—C31—C32 | −0.9 (7) |
S1—N1—C5—C6 | −1.6 (5) | C30—C31—C32—C33 | 0.6 (8) |
C2—N1—C5—C4 | 1.2 (4) | C31—C32—C33—C28 | 0.6 (8) |
S1—N1—C5—C4 | 177.0 (2) | C29—C28—C33—C32 | −1.4 (6) |
C4—C5—C6—C7 | 0.7 (6) | C27—C28—C33—C32 | −179.3 (4) |
N1—C5—C6—C7 | 179.1 (4) | O4—S3—C34—C35 | 152.0 (3) |
C5—C6—C7—C8 | −0.9 (6) | O3—S3—C34—C35 | 19.4 (4) |
C6—C7—C8—C9 | 0.6 (7) | N25—S3—C34—C35 | −93.8 (4) |
C7—C8—C9—C4 | 0.1 (6) | O4—S3—C34—C39 | −27.4 (4) |
C5—C4—C9—C8 | −0.3 (6) | O3—S3—C34—C39 | −160.1 (3) |
C3—C4—C9—C8 | −178.2 (4) | N25—S3—C34—C39 | 86.8 (3) |
O2—S1—C10—C11 | −140.5 (3) | C39—C34—C35—C36 | 1.4 (7) |
O1—S1—C10—C11 | −8.4 (3) | S3—C34—C35—C36 | −178.0 (4) |
N1—S1—C10—C11 | 105.3 (3) | C34—C35—C36—C37 | −0.9 (9) |
O2—S1—C10—C15 | 35.1 (3) | C35—C36—C37—C38 | 0.0 (10) |
O1—S1—C10—C15 | 167.2 (3) | C36—C37—C38—C39 | 0.4 (10) |
N1—S1—C10—C15 | −79.1 (3) | C37—C38—C39—C34 | 0.1 (8) |
C15—C10—C11—C12 | −0.7 (5) | C35—C34—C39—C38 | −1.1 (7) |
S1—C10—C11—C12 | 174.8 (3) | S3—C34—C39—C38 | 178.3 (4) |
C10—C11—C12—C13 | 0.2 (6) | C27—S4—C40—C41 | 23.7 (4) |
C11—C12—C13—C14 | 0.7 (7) | C27—S4—C40—C45 | −159.0 (3) |
C12—C13—C14—C15 | −1.1 (7) | C45—C40—C41—C42 | 0.0 (6) |
C13—C14—C15—C10 | 0.6 (6) | S4—C40—C41—C42 | 177.3 (3) |
C11—C10—C15—C14 | 0.3 (6) | C40—C41—C42—C43 | 0.1 (7) |
S1—C10—C15—C14 | −175.3 (3) | C41—C42—C43—C44 | 0.0 (8) |
C3—S2—C16—C21 | 153.3 (4) | C42—C43—C44—C45 | −0.3 (8) |
C3—S2—C16—C17 | −28.7 (4) | C43—C44—C45—C40 | 0.4 (8) |
C21—C16—C17—C18 | 1.7 (7) | C41—C40—C45—C44 | −0.3 (7) |
S2—C16—C17—C18 | −176.2 (4) | S4—C40—C45—C44 | −177.7 (4) |
C16—C17—C18—C19 | −0.8 (8) | C22—N23—C24—C26 | −67.2 (4) |
C17—C18—C19—C20 | 0.9 (9) | C46—N23—C24—C26 | 173.3 (3) |
C18—C19—C20—C21 | −1.9 (10) | C27—C26—C24—N23 | 101.6 (4) |
C19—C20—C21—C16 | 2.7 (9) | N25—C26—C24—N23 | −73.2 (4) |
C17—C16—C21—C20 | −2.6 (7) | N23—C46—C47—O5 | 77.5 (5) |
S2—C16—C21—C20 | 175.4 (4) | N23—C46—C47—O6B | −126.0 (5) |
C3—C2—C22—N23 | 106.1 (4) | N23—C46—C47—O6A | 173.8 (4) |
N1—C2—C22—N23 | −80.7 (4) | O5—C47—O6A—C49 | −154.1 (7) |
C2—C22—N23—C24 | 171.4 (3) | O6B—C47—O6A—C49 | −22.7 (6) |
C2—C22—N23—C46 | −69.0 (4) | C46—C47—O6A—C49 | 96.3 (7) |
C24—N23—C46—C47 | −80.3 (5) | O6B—C49—O6A—C47 | 22.4 (6) |
C22—N23—C46—C47 | 161.5 (4) | O5—C47—O6B—C49 | 88.1 (9) |
O4—S3—N25—C26 | 35.2 (3) | O6A—C47—O6B—C49 | 22.7 (6) |
O3—S3—N25—C26 | 165.4 (3) | C46—C47—O6B—C49 | −64.6 (9) |
C34—S3—N25—C26 | −80.0 (3) | O6A—C49—O6B—C47 | −22.4 (6) |
O4—S3—N25—C29 | −175.8 (3) | O6B—C47—O5—C48 | 35.9 (7) |
O3—S3—N25—C29 | −45.6 (3) | O6A—C47—O5—C48 | 85.8 (5) |
C34—S3—N25—C29 | 69.0 (3) | C46—C47—O5—C48 | −168.3 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1 | 0.93 | 2.37 | 2.923 (5) | 118 |
C11—H11···O1 | 0.93 | 2.57 | 2.924 (5) | 103 |
C15—H15···N23 | 0.93 | 2.48 | 3.334 (4) | 153 |
C22—H22A···O2 | 0.97 | 2.36 | 2.913 (4) | 115 |
C22—H22B···S2 | 0.97 | 2.85 | 3.311 (4) | 110 |
C24—H24A···O4 | 0.97 | 2.33 | 2.887 (4) | 116 |
C24—H24A···O5 | 0.97 | 2.39 | 3.090 (5) | 129 |
C24—H24B···S4 | 0.97 | 2.84 | 3.287 (4) | 109 |
C30—H30···O3 | 0.93 | 2.33 | 2.920 (5) | 121 |
C35—H35···O3 | 0.93 | 2.55 | 2.904 (5) | 103 |
C32—H32···CgAi | 0.93 | 2.95 | 3.728 (5) | 143 |
C32—H32···CgBi | 0.93 | 3.09 | 3.752 (5) | 129 |
C31—H31···CgCi | 0.93 | 2.99 | 3.680 (6) | 132 |
C7—H7···CgDii | 0.93 | 3.09 | 3.661 (5) | 122 |
C9—H9···CgHiii | 0.93 | 3.02 | 3.682 (5) | 130 |
Symmetry codes: (i) x+1, y, z; (ii) x−3/2, −y−1/2, z−3/2; (iii) x−1, y, z. |
Experimental details
Crystal data |
Chemical formula | C46H41N3O6S4 |
Mr | 857.03 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 10.7146 (1), 23.8939 (1), 16.8782 (3) |
β (°) | 91.846 (1) |
V (Å3) | 4318.81 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.27 |
Crystal size (mm) | 0.40 × 0.36 × 0.28 |
|
Data collection |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 29148, 10689, 5223 |
Rint | 0.066 |
(sin θ/λ)max (Å−1) | 0.672 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.074, 0.207, 1.01 |
No. of reflections | 10689 |
No. of parameters | 543 |
No. of restraints | 4 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.56, −0.45 |
Selected bond lengths (Å) topS1—O2 | 1.406 (3) | S3—O4 | 1.426 (3) |
S1—O1 | 1.427 (3) | S3—O3 | 1.432 (3) |
N1—C5 | 1.415 (4) | N25—C26 | 1.425 (4) |
N1—C2 | 1.421 (4) | N25—C29 | 1.435 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1 | 0.93 | 2.37 | 2.923 (5) | 118 |
C11—H11···O1 | 0.93 | 2.57 | 2.924 (5) | 103 |
C15—H15···N23 | 0.93 | 2.48 | 3.334 (4) | 153 |
C22—H22A···O2 | 0.97 | 2.36 | 2.913 (4) | 115 |
C22—H22B···S2 | 0.97 | 2.85 | 3.311 (4) | 110 |
C24—H24A···O4 | 0.97 | 2.33 | 2.887 (4) | 116 |
C24—H24A···O5 | 0.97 | 2.39 | 3.090 (5) | 129 |
C24—H24B···S4 | 0.97 | 2.84 | 3.287 (4) | 109 |
C30—H30···O3 | 0.93 | 2.33 | 2.920 (5) | 121 |
C35—H35···O3 | 0.93 | 2.55 | 2.904 (5) | 103 |
C32—H32···CgAi | 0.93 | 2.95 | 3.728 (5) | 143 |
C32—H32···CgBi | 0.93 | 3.09 | 3.752 (5) | 129 |
C31—H31···CgCi | 0.93 | 2.99 | 3.680 (6) | 132 |
C7—H7···CgDii | 0.93 | 3.09 | 3.661 (5) | 122 |
C9—H9···CgHiii | 0.93 | 3.02 | 3.682 (5) | 130 |
Symmetry codes: (i) x+1, y, z; (ii) x−3/2, −y−1/2, z−3/2; (iii) x−1, y, z. |
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Indole is a heterocyclic compound and is present in a large number of natural products. Many of these natural products and their synthetic derivatives have a wide range of biological activities, such as antibacterial (Okabe & Adachi, 1998), antitumour (Schollmeyer et al., 1995), antidepressant (Grinev et al., 1984), antimicrobial (El-Sayed et al., 1986; Gadaginamath & Patil, 1999) and anti-inflammatory (Rodriguez et al., 1985). Indoles have been proved to display high aldose reductose inhibitory activity (Rajeswaran et al., 1999). The interaction of phenylsulfonyl indole with the calf-thymus DNA by spectroscopic methods has also been studied (Sivaraman et al., 1996). The structure determination of the title compound, (I), was undertaken as part of our studies on indole derivatives.
The dihedral angle between the indole groups (AB and EF) and the phenyl rings (C, D, G and H) are AB/C = 75.0 (1)°, EF/G = 84.0 (1)°, AB/D = 84.9 (1)° and EF/H = 66.6 (1)°. The dihedral angle between rings C/D and G/H are 69.5 (1) and 77.8 (1)°, respectively. Atom N25 deviates by 0.217 (3) Å from the plane through atoms C26, C29 and S3, and the sum of the angles around N25 is 353.8 (2)°. This slight pyramidalization behaviour is also observed in related indole dervatives (Sankaranarayan et al., 2000, 2001; Sankaranarayan, Yogavel, Velmurugan, Sekar, Babu et al., 2003; Sankaranarayan, Yogavel, Velmurugan, Sekar, Srinivasan et al., 2003; SethuSankar et al., 2002; Ganesh et al., 2003; Krishna et al., 2003).
The molecular structure is stabilized by C—H···O, C—H···S and C—H···N interactions. The phenyl rings C of the molecules at (x, y, z) and (−x, −y, −z) are stacked in a face-to-face manner, with their centroids separated by 3.772 (2) Å. Several intermolecular edge-to-face interactions and several C—H···π interactions are also observed (Table 2). CgA, CgB, CgC, CgD and CgH are the centroid of the rings A, B, C, D and H, respectively. Thus, the crystal packing is stabilized by C—H···π, face-to-face π–π and edge-to-face π–π interactions.