Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270199015991/qb0144sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270199015991/qb0144Isup2.hkl |
CCDC reference: 140862
A mixture of 1 mmol (1R,2R)-diphenylethylenediamine and 2 mmol 8-quinolinesulfonyl chloride in 10 ml dichloroethane was stirred for 24 h at room temperature. Then the resulting white solid was collected by evaporation of the solution. The yield of analytically pure product was 100%. The single-crystal was obtained from acetone at room temperature.
The H atoms bonded to N1 and N3 were refined isotropically; all other H atoms were allowed for as riding atoms. N—H dimensions are 0.78 (3) and 0.80 (3) Å.
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS (Siemens, 1994); data reduction: SHELXTL (Sheldrick, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELXTL (Sheldrick, 1994).
C32H26N4O4S2·C3H6O | F(000) = 684 |
Mr = 652.77 | Dx = 1.350 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.717 (2) Å | Cell parameters from 33 reflections |
b = 9.495 (1) Å | θ = 3.2–16.5° |
c = 17.542 (3) Å | µ = 0.22 mm−1 |
β = 97.13 (1)° | T = 296 K |
V = 1606.0 (5) Å3 | Flake, colorless |
Z = 2 | 0.48 × 0.40 × 0.36 mm |
P4 diffractometer | Rint = 0.012 |
Radiation source: fine-focus sealed tube | θmax = 27°, θmin = 2.1° |
Graphite monochromator | h = −1→12 |
ω scans | k = −1→12 |
5056 measured reflections | l = −22→22 |
4159 independent reflections | 3 standard reflections every 97 reflections |
3405 reflections with I > 2σ(I) | intensity decay: 1.4% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.032 | w = 1/[σ2(Fo2) + (0.0439P)2] where P = Fo2 + 2Fc2)/3 |
wR(F2) = 0.074 | (Δ/σ)max < 0.001 |
S = 0.94 | Δρmax = 0.21 e Å−3 |
4159 reflections | Δρmin = −0.18 e Å−3 |
426 parameters | Extinction correction: SHELXL, Fc* = kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0146 (11) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 433 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.05 (6) |
C32H26N4O4S2·C3H6O | V = 1606.0 (5) Å3 |
Mr = 652.77 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 9.717 (2) Å | µ = 0.22 mm−1 |
b = 9.495 (1) Å | T = 296 K |
c = 17.542 (3) Å | 0.48 × 0.40 × 0.36 mm |
β = 97.13 (1)° |
P4 diffractometer | Rint = 0.012 |
5056 measured reflections | 3 standard reflections every 97 reflections |
4159 independent reflections | intensity decay: 1.4% |
3405 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.074 | Δρmax = 0.21 e Å−3 |
S = 0.94 | Δρmin = −0.18 e Å−3 |
4159 reflections | Absolute structure: Flack (1983), 433 Friedel pairs |
426 parameters | Absolute structure parameter: −0.05 (6) |
1 restraint |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.77133 (6) | 0.13569 (7) | 0.29480 (3) | 0.03750 (16) | |
S2 | 0.46361 (7) | 0.59288 (7) | 0.24829 (3) | 0.04496 (18) | |
O1 | 0.81699 (18) | 0.1436 (2) | 0.37498 (9) | 0.0511 (5) | |
O2 | 0.63801 (16) | 0.0750 (2) | 0.26972 (10) | 0.0504 (5) | |
O3 | 0.32708 (19) | 0.5603 (3) | 0.26519 (11) | 0.0649 (6) | |
O4 | 0.4834 (2) | 0.7064 (2) | 0.19724 (11) | 0.0638 (6) | |
N1 | 0.7677 (2) | 0.2949 (3) | 0.26177 (12) | 0.0373 (5) | |
N2 | 1.0766 (2) | 0.1945 (3) | 0.29681 (12) | 0.0423 (5) | |
N3 | 0.5276 (2) | 0.4517 (3) | 0.21404 (13) | 0.0399 (5) | |
N4 | 0.5346 (2) | 0.3919 (2) | 0.37985 (12) | 0.0420 (5) | |
C1 | 0.8464 (3) | 0.2347 (4) | 0.06880 (16) | 0.0570 (8) | |
H1 | 0.7695 | 0.1781 | 0.0541 | 0.068* | |
C2 | 0.9575 (4) | 0.2344 (4) | 0.02586 (19) | 0.0795 (11) | |
H2 | 0.9554 | 0.1766 | −0.0171 | 0.095* | |
C3 | 1.0703 (4) | 0.3193 (4) | 0.0468 (2) | 0.0746 (11) | |
H3 | 1.1431 | 0.3210 | 0.0170 | 0.090* | |
C4 | 1.0758 (3) | 0.4011 (4) | 0.11105 (18) | 0.0616 (9) | |
H4 | 1.1536 | 0.4563 | 0.1259 | 0.074* | |
C5 | 0.9655 (3) | 0.4021 (3) | 0.15418 (15) | 0.0481 (7) | |
H5 | 0.9691 | 0.4591 | 0.1975 | 0.058* | |
C6 | 0.8503 (3) | 0.3192 (3) | 0.13343 (13) | 0.0384 (6) | |
C7 | 0.7269 (2) | 0.3202 (3) | 0.17945 (13) | 0.0341 (6) | |
H7 | 0.6639 | 0.2444 | 0.1598 | 0.041* | |
C8 | 0.8923 (2) | 0.0335 (3) | 0.25102 (13) | 0.0369 (6) | |
C9 | 0.8478 (3) | −0.0844 (3) | 0.21041 (16) | 0.0491 (7) | |
H9 | 0.7542 | −0.1077 | 0.2045 | 0.059* | |
C10 | 0.9418 (4) | −0.1705 (4) | 0.17759 (18) | 0.0641 (9) | |
H10 | 0.9100 | −0.2489 | 0.1489 | 0.077* | |
C11 | 1.0787 (3) | −0.1398 (4) | 0.18756 (18) | 0.0636 (9) | |
H11 | 1.1406 | −0.2005 | 0.1679 | 0.076* | |
C12 | 1.1292 (3) | −0.0186 (4) | 0.22689 (15) | 0.0476 (7) | |
C13 | 1.0358 (2) | 0.0723 (3) | 0.25941 (13) | 0.0363 (6) | |
C14 | 1.2098 (3) | 0.2253 (4) | 0.30157 (15) | 0.0541 (8) | |
H14 | 1.2395 | 0.3096 | 0.3251 | 0.065* | |
C15 | 1.3095 (3) | 0.1395 (5) | 0.27354 (17) | 0.0636 (9) | |
H15 | 1.4024 | 0.1659 | 0.2803 | 0.076* | |
C16 | 1.2710 (3) | 0.0198 (4) | 0.23711 (17) | 0.0589 (9) | |
H16 | 1.3368 | −0.0379 | 0.2186 | 0.071* | |
C17 | 0.6778 (3) | 0.5524 (3) | 0.03745 (14) | 0.0526 (7) | |
H17 | 0.7598 | 0.5949 | 0.0589 | 0.063* | |
C18 | 0.6392 (3) | 0.5595 (4) | −0.04114 (15) | 0.0603 (8) | |
H18 | 0.6952 | 0.6067 | −0.0720 | 0.072* | |
C19 | 0.5200 (3) | 0.4979 (4) | −0.07322 (14) | 0.0553 (8) | |
H19 | 0.4942 | 0.5027 | −0.1260 | 0.066* | |
C20 | 0.4380 (3) | 0.4288 (5) | −0.02752 (16) | 0.0683 (10) | |
H20 | 0.3564 | 0.3863 | −0.0495 | 0.082* | |
C21 | 0.4749 (3) | 0.4211 (4) | 0.05077 (14) | 0.0540 (8) | |
H21 | 0.4179 | 0.3740 | 0.0812 | 0.065* | |
C22 | 0.5961 (2) | 0.4832 (3) | 0.08436 (13) | 0.0356 (5) | |
C23 | 0.6458 (2) | 0.4613 (3) | 0.16909 (12) | 0.0338 (5) | |
H23 | 0.7064 | 0.5393 | 0.1883 | 0.041* | |
C24 | 0.5654 (3) | 0.6295 (3) | 0.33742 (13) | 0.0409 (6) | |
C25 | 0.6184 (3) | 0.7616 (3) | 0.34956 (17) | 0.0524 (8) | |
H25 | 0.6031 | 0.8294 | 0.3111 | 0.063* | |
C26 | 0.6964 (4) | 0.7955 (4) | 0.42025 (18) | 0.0653 (9) | |
H26 | 0.7331 | 0.8855 | 0.4283 | 0.078* | |
C27 | 0.7181 (3) | 0.6976 (4) | 0.47662 (18) | 0.0622 (9) | |
H27 | 0.7695 | 0.7213 | 0.5231 | 0.075* | |
C28 | 0.6639 (3) | 0.5600 (3) | 0.46587 (15) | 0.0487 (7) | |
C29 | 0.5862 (3) | 0.5236 (3) | 0.39472 (14) | 0.0404 (6) | |
C30 | 0.5557 (3) | 0.2990 (3) | 0.43453 (15) | 0.0505 (7) | |
H30 | 0.5220 | 0.2084 | 0.4243 | 0.061* | |
C31 | 0.6259 (3) | 0.3262 (4) | 0.50787 (17) | 0.0589 (9) | |
H31 | 0.6346 | 0.2562 | 0.5452 | 0.071* | |
C32 | 0.6800 (3) | 0.4539 (4) | 0.52334 (15) | 0.0580 (8) | |
H32 | 0.7280 | 0.4732 | 0.5714 | 0.070* | |
O5 | 0.9053 (2) | 0.5499 (3) | 0.32269 (12) | 0.0704 (6) | |
C33 | 0.9916 (3) | 0.5811 (4) | 0.37568 (17) | 0.0598 (8) | |
C34 | 1.0509 (4) | 0.7258 (5) | 0.3805 (2) | 0.0843 (12) | |
H34A | 1.1350 | 0.7273 | 0.3570 | 0.101* | .001 |
H34B | 1.0707 | 0.7530 | 0.4335 | 0.101* | .001 |
H34C | 0.9854 | 0.7904 | 0.3543 | 0.101* | .001 |
C35 | 1.0382 (5) | 0.4750 (6) | 0.4339 (2) | 0.1198 (18) | |
H35A | 0.9856 | 0.3901 | 0.4234 | 0.144* | .001 |
H35B | 1.0247 | 0.5098 | 0.4838 | 0.144* | .001 |
H35C | 1.1348 | 0.4555 | 0.4325 | 0.144* | .001 |
H1N | 0.834 (3) | 0.341 (3) | 0.2766 (15) | 0.043 (9)* | |
H3N | 0.535 (3) | 0.390 (3) | 0.2437 (15) | 0.036 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0318 (3) | 0.0398 (4) | 0.0419 (3) | 0.0042 (3) | 0.0083 (2) | 0.0107 (3) |
S2 | 0.0509 (4) | 0.0448 (4) | 0.0393 (3) | 0.0147 (3) | 0.0061 (3) | 0.0040 (3) |
O1 | 0.0535 (10) | 0.0607 (12) | 0.0403 (9) | 0.0161 (11) | 0.0111 (8) | 0.0147 (10) |
O2 | 0.0311 (8) | 0.0480 (12) | 0.0727 (11) | 0.0004 (9) | 0.0090 (8) | 0.0158 (11) |
O3 | 0.0449 (10) | 0.0844 (17) | 0.0652 (12) | 0.0186 (12) | 0.0062 (9) | −0.0043 (13) |
O4 | 0.1001 (16) | 0.0482 (13) | 0.0443 (10) | 0.0238 (13) | 0.0133 (11) | 0.0122 (10) |
N1 | 0.0387 (12) | 0.0382 (13) | 0.0341 (11) | −0.0002 (11) | 0.0012 (10) | 0.0028 (10) |
N2 | 0.0362 (11) | 0.0438 (13) | 0.0471 (11) | −0.0011 (11) | 0.0055 (9) | 0.0008 (11) |
N3 | 0.0497 (14) | 0.0369 (13) | 0.0340 (11) | 0.0040 (11) | 0.0085 (10) | 0.0043 (11) |
N4 | 0.0472 (13) | 0.0416 (13) | 0.0385 (11) | −0.0017 (11) | 0.0098 (10) | 0.0042 (11) |
C1 | 0.0639 (18) | 0.0533 (19) | 0.0555 (16) | −0.0044 (17) | 0.0142 (15) | −0.0107 (15) |
C2 | 0.108 (3) | 0.075 (3) | 0.063 (2) | 0.006 (3) | 0.040 (2) | −0.015 (2) |
C3 | 0.068 (2) | 0.083 (3) | 0.079 (2) | 0.009 (2) | 0.0377 (19) | 0.007 (2) |
C4 | 0.0457 (17) | 0.077 (2) | 0.0638 (19) | −0.0001 (17) | 0.0134 (14) | 0.0147 (19) |
C5 | 0.0454 (16) | 0.0552 (19) | 0.0435 (14) | −0.0019 (15) | 0.0047 (12) | 0.0054 (14) |
C6 | 0.0445 (14) | 0.0376 (14) | 0.0336 (12) | 0.0065 (12) | 0.0070 (11) | 0.0045 (11) |
C7 | 0.0399 (13) | 0.0312 (14) | 0.0301 (11) | −0.0007 (11) | −0.0005 (10) | 0.0008 (10) |
C8 | 0.0361 (13) | 0.0366 (14) | 0.0376 (12) | 0.0030 (12) | 0.0034 (10) | 0.0038 (11) |
C9 | 0.0475 (16) | 0.0473 (18) | 0.0518 (15) | −0.0037 (14) | 0.0027 (13) | −0.0025 (14) |
C10 | 0.076 (2) | 0.053 (2) | 0.0628 (19) | −0.0006 (19) | 0.0047 (17) | −0.0224 (17) |
C11 | 0.066 (2) | 0.061 (2) | 0.068 (2) | 0.0153 (19) | 0.0209 (17) | −0.0122 (18) |
C12 | 0.0423 (14) | 0.0588 (19) | 0.0434 (14) | 0.0093 (15) | 0.0115 (11) | 0.0027 (14) |
C13 | 0.0332 (12) | 0.0410 (15) | 0.0347 (11) | 0.0059 (12) | 0.0041 (9) | 0.0057 (12) |
C14 | 0.0410 (15) | 0.066 (2) | 0.0542 (16) | −0.0124 (16) | 0.0008 (13) | 0.0035 (16) |
C15 | 0.0311 (13) | 0.098 (3) | 0.0620 (17) | −0.0035 (19) | 0.0072 (12) | 0.011 (2) |
C16 | 0.0419 (16) | 0.081 (2) | 0.0563 (17) | 0.0144 (17) | 0.0170 (13) | 0.0078 (18) |
C17 | 0.0607 (17) | 0.0518 (18) | 0.0433 (13) | −0.0188 (16) | −0.0018 (12) | 0.0103 (14) |
C18 | 0.076 (2) | 0.064 (2) | 0.0408 (13) | −0.0149 (19) | 0.0085 (13) | 0.0138 (16) |
C19 | 0.0639 (19) | 0.070 (2) | 0.0303 (12) | 0.0047 (18) | −0.0013 (12) | 0.0014 (14) |
C20 | 0.0527 (18) | 0.103 (3) | 0.0452 (15) | −0.017 (2) | −0.0095 (13) | 0.0049 (19) |
C21 | 0.0414 (15) | 0.080 (2) | 0.0399 (14) | −0.0151 (16) | 0.0007 (12) | 0.0094 (16) |
C22 | 0.0390 (13) | 0.0327 (13) | 0.0349 (11) | 0.0029 (12) | 0.0028 (10) | 0.0026 (11) |
C23 | 0.0368 (13) | 0.0320 (13) | 0.0319 (11) | −0.0035 (12) | 0.0020 (9) | 0.0009 (11) |
C24 | 0.0476 (13) | 0.0413 (15) | 0.0361 (11) | 0.0025 (14) | 0.0143 (10) | 0.0012 (12) |
C25 | 0.070 (2) | 0.0404 (17) | 0.0508 (16) | 0.0020 (16) | 0.0221 (15) | −0.0003 (14) |
C26 | 0.083 (2) | 0.0497 (19) | 0.065 (2) | −0.0160 (19) | 0.0177 (18) | −0.0113 (17) |
C27 | 0.069 (2) | 0.067 (2) | 0.0502 (16) | −0.0122 (19) | 0.0054 (15) | −0.0164 (18) |
C28 | 0.0482 (16) | 0.058 (2) | 0.0411 (13) | 0.0009 (15) | 0.0103 (11) | −0.0023 (14) |
C29 | 0.0402 (14) | 0.0447 (16) | 0.0388 (13) | 0.0017 (13) | 0.0147 (11) | 0.0008 (12) |
C30 | 0.0544 (17) | 0.0473 (17) | 0.0511 (16) | −0.0023 (15) | 0.0112 (14) | 0.0102 (14) |
C31 | 0.0618 (19) | 0.066 (2) | 0.0496 (17) | 0.0072 (18) | 0.0086 (15) | 0.0199 (16) |
C32 | 0.0618 (19) | 0.075 (2) | 0.0366 (14) | −0.0003 (19) | 0.0026 (13) | 0.0025 (16) |
O5 | 0.0738 (15) | 0.0680 (16) | 0.0654 (13) | −0.0070 (13) | −0.0069 (11) | −0.0121 (12) |
C33 | 0.0586 (18) | 0.065 (2) | 0.0538 (16) | 0.0028 (18) | −0.0011 (14) | −0.0121 (17) |
C34 | 0.080 (3) | 0.082 (3) | 0.085 (2) | −0.022 (2) | −0.013 (2) | −0.001 (2) |
C35 | 0.170 (5) | 0.097 (4) | 0.081 (3) | 0.056 (4) | −0.027 (3) | 0.005 (3) |
S1—O1 | 1.4234 (17) | C10—C11 | 1.352 (4) |
S1—O2 | 1.4360 (19) | C11—C12 | 1.399 (5) |
S1—N1 | 1.617 (2) | C12—C16 | 1.416 (4) |
S1—C8 | 1.771 (3) | C12—C13 | 1.422 (4) |
S2—O3 | 1.429 (2) | C14—C15 | 1.401 (5) |
S2—O4 | 1.429 (2) | C15—C16 | 1.334 (5) |
S2—N3 | 1.624 (2) | C17—C22 | 1.379 (3) |
S2—C24 | 1.778 (3) | C17—C18 | 1.385 (3) |
N1—C7 | 1.469 (3) | C18—C19 | 1.356 (4) |
N2—C14 | 1.319 (3) | C19—C20 | 1.366 (4) |
N2—C13 | 1.367 (3) | C20—C21 | 1.377 (4) |
N3—C23 | 1.474 (3) | C21—C22 | 1.382 (3) |
N4—C30 | 1.300 (3) | C22—C23 | 1.519 (3) |
N4—C29 | 1.360 (3) | C24—C25 | 1.362 (4) |
C1—C6 | 1.386 (4) | C24—C29 | 1.419 (4) |
C1—C2 | 1.391 (4) | C25—C26 | 1.408 (4) |
C2—C3 | 1.373 (5) | C26—C27 | 1.355 (5) |
C3—C4 | 1.365 (5) | C27—C28 | 1.413 (5) |
C4—C5 | 1.387 (4) | C28—C29 | 1.419 (4) |
C5—C6 | 1.380 (4) | C28—C32 | 1.420 (4) |
C6—C7 | 1.526 (3) | C30—C31 | 1.403 (4) |
C7—C23 | 1.553 (4) | C31—C32 | 1.336 (5) |
C8—C9 | 1.368 (4) | O5—C33 | 1.209 (3) |
C8—C13 | 1.432 (3) | C33—C35 | 1.465 (5) |
C9—C10 | 1.401 (4) | C33—C34 | 1.488 (5) |
O1—S1—O2 | 118.85 (11) | N2—C13—C12 | 123.1 (2) |
O1—S1—N1 | 107.16 (13) | N2—C13—C8 | 119.2 (2) |
O2—S1—N1 | 106.63 (12) | C12—C13—C8 | 117.7 (2) |
O1—S1—C8 | 108.36 (11) | N2—C14—C15 | 124.3 (3) |
O2—S1—C8 | 105.63 (12) | C16—C15—C14 | 119.9 (3) |
N1—S1—C8 | 110.07 (11) | C15—C16—C12 | 119.4 (3) |
O3—S2—O4 | 119.60 (14) | C22—C17—C18 | 120.8 (3) |
O3—S2—N3 | 107.82 (14) | C19—C18—C17 | 120.3 (3) |
O4—S2—N3 | 107.64 (12) | C18—C19—C20 | 119.6 (2) |
O3—S2—C24 | 106.83 (11) | C19—C20—C21 | 120.8 (3) |
O4—S2—C24 | 107.45 (14) | C20—C21—C22 | 120.3 (3) |
N3—S2—C24 | 106.87 (12) | C17—C22—C21 | 118.2 (2) |
C7—N1—S1 | 119.77 (19) | C17—C22—C23 | 120.9 (2) |
C14—N2—C13 | 116.3 (2) | C21—C22—C23 | 120.6 (2) |
C23—N3—S2 | 120.41 (19) | N3—C23—C22 | 110.97 (19) |
C30—N4—C29 | 117.5 (2) | N3—C23—C7 | 107.6 (2) |
C6—C1—C2 | 120.0 (3) | C22—C23—C7 | 109.12 (19) |
C3—C2—C1 | 120.1 (3) | C25—C24—C29 | 121.6 (2) |
C4—C3—C2 | 120.2 (3) | C25—C24—S2 | 118.4 (2) |
C3—C4—C5 | 120.0 (3) | C29—C24—S2 | 119.9 (2) |
C6—C5—C4 | 120.6 (3) | C24—C25—C26 | 120.0 (3) |
C5—C6—C1 | 119.0 (3) | C27—C26—C25 | 120.3 (3) |
C5—C6—C7 | 121.4 (2) | C26—C27—C28 | 121.0 (3) |
C1—C6—C7 | 119.5 (2) | C27—C28—C29 | 119.4 (3) |
N1—C7—C6 | 112.67 (19) | C27—C28—C32 | 123.7 (3) |
N1—C7—C23 | 109.10 (19) | C29—C28—C32 | 116.8 (3) |
C6—C7—C23 | 111.4 (2) | N4—C29—C24 | 120.0 (2) |
C9—C8—C13 | 120.3 (2) | N4—C29—C28 | 122.4 (2) |
C9—C8—S1 | 119.4 (2) | C24—C29—C28 | 117.6 (3) |
C13—C8—S1 | 120.3 (2) | N4—C30—C31 | 124.4 (3) |
C8—C9—C10 | 120.8 (3) | C32—C31—C30 | 119.2 (3) |
C11—C10—C9 | 120.1 (3) | C31—C32—C28 | 119.6 (3) |
C10—C11—C12 | 121.4 (3) | O5—C33—C35 | 119.5 (4) |
C11—C12—C16 | 123.4 (3) | O5—C33—C34 | 119.8 (3) |
C11—C12—C13 | 119.7 (3) | C35—C33—C34 | 120.7 (3) |
C16—C12—C13 | 116.9 (3) | ||
O1—S1—N1—C7 | 178.71 (18) | C13—C12—C16—C15 | −2.4 (4) |
O2—S1—N1—C7 | −53.0 (2) | C22—C17—C18—C19 | −0.1 (5) |
C8—S1—N1—C7 | 61.1 (2) | C17—C18—C19—C20 | 0.0 (5) |
O3—S2—N3—C23 | 160.61 (18) | C18—C19—C20—C21 | 0.1 (6) |
O4—S2—N3—C23 | 30.3 (2) | C19—C20—C21—C22 | −0.2 (6) |
C24—S2—N3—C23 | −84.9 (2) | C18—C17—C22—C21 | 0.0 (4) |
C6—C1—C2—C3 | −1.0 (5) | C18—C17—C22—C23 | 173.2 (3) |
C1—C2—C3—C4 | 2.0 (6) | C20—C21—C22—C17 | 0.2 (5) |
C2—C3—C4—C5 | −2.0 (6) | C20—C21—C22—C23 | −173.0 (3) |
C3—C4—C5—C6 | 1.0 (5) | S2—N3—C23—C22 | −88.4 (2) |
C4—C5—C6—C1 | 0.1 (4) | S2—N3—C23—C7 | 152.26 (17) |
C4—C5—C6—C7 | −179.2 (3) | C17—C22—C23—N3 | 152.2 (3) |
C2—C1—C6—C5 | −0.1 (5) | C21—C22—C23—N3 | −34.8 (3) |
C2—C1—C6—C7 | 179.2 (3) | C17—C22—C23—C7 | −89.4 (3) |
S1—N1—C7—C6 | −90.6 (3) | C21—C22—C23—C7 | 83.6 (3) |
S1—N1—C7—C23 | 145.18 (18) | N1—C7—C23—N3 | −56.1 (2) |
C5—C6—C7—N1 | −52.6 (3) | C6—C7—C23—N3 | 178.87 (19) |
C1—C6—C7—N1 | 128.2 (3) | N1—C7—C23—C22 | −176.6 (2) |
C5—C6—C7—C23 | 70.3 (3) | C6—C7—C23—C22 | 58.4 (2) |
C1—C6—C7—C23 | −108.9 (3) | O3—S2—C24—C25 | −116.2 (2) |
O1—S1—C8—C9 | 122.4 (2) | O4—S2—C24—C25 | 13.3 (3) |
O2—S1—C8—C9 | −6.0 (2) | N3—S2—C24—C25 | 128.6 (2) |
N1—S1—C8—C9 | −120.7 (2) | O3—S2—C24—C29 | 61.9 (2) |
O1—S1—C8—C13 | −56.3 (2) | O4—S2—C24—C29 | −168.61 (19) |
O2—S1—C8—C13 | 175.29 (19) | N3—S2—C24—C29 | −53.3 (2) |
N1—S1—C8—C13 | 60.5 (2) | C29—C24—C25—C26 | 0.2 (4) |
C13—C8—C9—C10 | 1.2 (4) | S2—C24—C25—C26 | 178.3 (2) |
S1—C8—C9—C10 | −177.5 (2) | C24—C25—C26—C27 | −0.5 (5) |
C8—C9—C10—C11 | 1.8 (5) | C25—C26—C27—C28 | 0.2 (5) |
C9—C10—C11—C12 | −3.5 (5) | C26—C27—C28—C29 | 0.4 (5) |
C10—C11—C12—C16 | −178.4 (3) | C26—C27—C28—C32 | −178.3 (3) |
C10—C11—C12—C13 | 2.1 (5) | C30—N4—C29—C24 | −179.5 (2) |
C14—N2—C13—C12 | 0.0 (3) | C30—N4—C29—C28 | 1.9 (4) |
C14—N2—C13—C8 | −179.0 (2) | C25—C24—C29—N4 | −178.3 (3) |
C11—C12—C13—N2 | −178.1 (2) | S2—C24—C29—N4 | 3.6 (3) |
C16—C12—C13—N2 | 2.3 (4) | C25—C24—C29—C28 | 0.4 (4) |
C11—C12—C13—C8 | 0.8 (4) | S2—C24—C29—C28 | −177.69 (19) |
C16—C12—C13—C8 | −178.7 (2) | C27—C28—C29—N4 | 178.0 (3) |
C9—C8—C13—N2 | 176.6 (2) | C32—C28—C29—N4 | −3.2 (4) |
S1—C8—C13—N2 | −4.7 (3) | C27—C28—C29—C24 | −0.6 (4) |
C9—C8—C13—C12 | −2.4 (3) | C32—C28—C29—C24 | 178.1 (2) |
S1—C8—C13—C12 | 176.27 (18) | C29—N4—C30—C31 | 1.0 (4) |
C13—N2—C14—C15 | −2.3 (4) | N4—C30—C31—C32 | −2.5 (5) |
N2—C14—C15—C16 | 2.2 (5) | C30—C31—C32—C28 | 0.9 (5) |
C14—C15—C16—C12 | 0.3 (4) | C27—C28—C32—C31 | −179.6 (3) |
C11—C12—C16—C15 | 178.1 (3) | C29—C28—C32—C31 | 1.7 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O5 | 0.80 (3) | 2.22 (3) | 2.905 (4) | 145 (3) |
N3—H3N···N1 | 0.78 (3) | 2.42 (3) | 2.806 (3) | 112 (2) |
N3—H3N···N4 | 0.78 (3) | 2.39 (3) | 2.956 (3) | 130 (3) |
Experimental details
Crystal data | |
Chemical formula | C32H26N4O4S2·C3H6O |
Mr | 652.77 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 296 |
a, b, c (Å) | 9.717 (2), 9.495 (1), 17.542 (3) |
β (°) | 97.13 (1) |
V (Å3) | 1606.0 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.48 × 0.40 × 0.36 |
Data collection | |
Diffractometer | P4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5056, 4159, 3405 |
Rint | 0.012 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.074, 0.94 |
No. of reflections | 4159 |
No. of parameters | 426 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.18 |
Absolute structure | Flack (1983), 433 Friedel pairs |
Absolute structure parameter | −0.05 (6) |
Computer programs: XSCANS (Siemens, 1994), SHELXTL (Sheldrick, 1994), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997b).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O5 | 0.80 (3) | 2.22 (3) | 2.905 (4) | 145 (3) |
N3—H3N···N1 | 0.78 (3) | 2.42 (3) | 2.806 (3) | 112 (2) |
N3—H3N···N4 | 0.78 (3) | 2.39 (3) | 2.956 (3) | 130 (3) |
The structure of the title compound, (I), has been determined as part of a study into asymmetric catalysis in transfer hydrogenation reaction and addition of dialkylzinc to aldehydes. Further study shows that BQSDA as chiral catalyst has high enantioselectivity. Therefore the structure of this new ligand can help us know of its catalytic mechanism in asymmetric reaction.