In the title compound, C
21H
23BrN
2O
2S
2, the two pyrrolidine rings adopt envelope conformations and the thiazolidine ring adopts a twisted conformation with a pseudo-twofold axis passing through the S atom and the C—N ring-fusion bond. The crystal packing is stabilized by a C—H

π interaction between inversion-related molecules.
Supporting information
CCDC reference: 610813
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.043
- wR factor = 0.126
- Data-to-parameter ratio = 19.5
checkCIF/PLATON results
No syntax errors found
Alert level C
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 C7
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 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: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
3-(4-Bromophenyl)-6-(
p-tosyl)perhydrothiazolidino[3,4-
a]pyrrolo[4,5-
c]pyrrole
top
Crystal data top
C21H23BrN2O2S2 | F(000) = 984 |
Mr = 479.44 | Dx = 1.525 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2ybc | Cell parameters from 2455 reflections |
a = 15.3215 (8) Å | θ = 2.4–25.0° |
b = 8.0676 (4) Å | µ = 2.19 mm−1 |
c = 17.1663 (9) Å | T = 293 K |
β = 100.119 (1)° | Block, colorless |
V = 2088.88 (19) Å3 | 0.23 × 0.22 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3520 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
Graphite monochromator | θmax = 28.0°, θmin = 2.4° |
ω scans | h = −19→20 |
23302 measured reflections | k = −10→10 |
4943 independent reflections | l = −22→21 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 0.96 | w = 1/[σ2(Fo2) + (0.0658P)2 + 1.1265P] where P = (Fo2 + 2Fc2)/3 |
4943 reflections | (Δ/σ)max = 0.001 |
254 parameters | Δρmax = 0.89 e Å−3 |
0 restraints | Δρmin = −0.53 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 | |
C1 | 0.84615 (18) | 0.0988 (3) | 0.72389 (17) | 0.0540 (6) | |
H1A | 0.8841 | 0.0589 | 0.7714 | 0.065* | |
H1B | 0.8815 | 0.1158 | 0.6829 | 0.065* | |
C2 | 0.77005 (18) | −0.0203 (3) | 0.69671 (16) | 0.0532 (6) | |
H2 | 0.7859 | −0.1337 | 0.7140 | 0.064* | |
C3 | 0.69206 (17) | 0.0453 (3) | 0.73441 (14) | 0.0482 (6) | |
H3 | 0.6719 | −0.0379 | 0.7689 | 0.058* | |
C4 | 0.72754 (18) | 0.1993 (4) | 0.78071 (15) | 0.0565 (7) | |
H4A | 0.6822 | 0.2839 | 0.7781 | 0.068* | |
H4B | 0.7500 | 0.1729 | 0.8357 | 0.068* | |
C5 | 0.73505 (19) | −0.0135 (4) | 0.60686 (17) | 0.0630 (7) | |
H5A | 0.7556 | 0.0857 | 0.5838 | 0.076* | |
H5B | 0.7543 | −0.1098 | 0.5806 | 0.076* | |
C6 | 0.63544 (18) | −0.0117 (4) | 0.59983 (15) | 0.0556 (6) | |
H6 | 0.6079 | 0.0417 | 0.5503 | 0.067* | |
C7 | 0.5946 (2) | −0.1826 (4) | 0.6073 (2) | 0.0804 (10) | |
H7A | 0.6369 | −0.2550 | 0.6395 | 0.096* | |
H7B | 0.5772 | −0.2326 | 0.5555 | 0.096* | |
C8 | 0.53218 (17) | 0.0670 (3) | 0.68142 (14) | 0.0454 (5) | |
H8 | 0.5321 | 0.0806 | 0.7381 | 0.055* | |
C9 | 0.46739 (16) | 0.1899 (3) | 0.63676 (13) | 0.0445 (5) | |
C10 | 0.37710 (18) | 0.1593 (4) | 0.62249 (18) | 0.0588 (7) | |
H10 | 0.3561 | 0.0612 | 0.6409 | 0.071* | |
C11 | 0.31761 (19) | 0.2695 (4) | 0.58193 (18) | 0.0620 (7) | |
H11 | 0.2572 | 0.2460 | 0.5725 | 0.074* | |
C12 | 0.34864 (19) | 0.4148 (3) | 0.55560 (16) | 0.0523 (6) | |
C13 | 0.43683 (19) | 0.4530 (3) | 0.57120 (16) | 0.0525 (6) | |
H13 | 0.4568 | 0.5536 | 0.5545 | 0.063* | |
C14 | 0.49621 (17) | 0.3404 (3) | 0.61209 (15) | 0.0508 (6) | |
H14 | 0.5563 | 0.3664 | 0.6231 | 0.061* | |
C15 | 0.92081 (16) | 0.3577 (3) | 0.86381 (15) | 0.0480 (6) | |
C16 | 1.00308 (16) | 0.2837 (3) | 0.86655 (16) | 0.0526 (6) | |
H16 | 1.0275 | 0.2733 | 0.8209 | 0.063* | |
C17 | 1.04820 (17) | 0.2257 (3) | 0.93808 (17) | 0.0556 (6) | |
H17 | 1.1034 | 0.1765 | 0.9401 | 0.067* | |
C18 | 1.01330 (17) | 0.2390 (3) | 1.00698 (16) | 0.0537 (6) | |
C19 | 0.93174 (18) | 0.3150 (4) | 1.00231 (16) | 0.0597 (7) | |
H19 | 0.9075 | 0.3262 | 1.0480 | 0.072* | |
C20 | 0.88525 (17) | 0.3748 (4) | 0.93168 (17) | 0.0568 (7) | |
H20 | 0.8306 | 0.4260 | 0.9300 | 0.068* | |
C21 | 1.0614 (2) | 0.1723 (4) | 1.08423 (18) | 0.0710 (8) | |
H21A | 1.0934 | 0.0741 | 1.0748 | 0.107* | |
H21B | 1.0195 | 0.1458 | 1.1178 | 0.107* | |
H21C | 1.1023 | 0.2542 | 1.1095 | 0.107* | |
N1 | 0.79942 (13) | 0.2525 (2) | 0.73956 (12) | 0.0468 (5) | |
N2 | 0.62166 (13) | 0.0881 (2) | 0.66776 (11) | 0.0442 (5) | |
O1 | 0.91716 (16) | 0.4435 (3) | 0.71811 (14) | 0.0750 (6) | |
O2 | 0.79610 (15) | 0.5403 (2) | 0.78499 (15) | 0.0743 (6) | |
S1 | 0.49934 (5) | −0.15093 (9) | 0.65325 (5) | 0.0620 (2) | |
S2 | 0.85767 (5) | 0.41492 (8) | 0.77173 (4) | 0.05425 (18) | |
Br1 | 0.26971 (3) | 0.56048 (5) | 0.49167 (3) | 0.08586 (17) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0499 (14) | 0.0543 (15) | 0.0555 (15) | 0.0063 (11) | 0.0028 (12) | −0.0053 (12) |
C2 | 0.0584 (15) | 0.0432 (13) | 0.0560 (15) | 0.0030 (11) | 0.0041 (12) | −0.0024 (11) |
C3 | 0.0554 (14) | 0.0498 (14) | 0.0392 (12) | −0.0104 (11) | 0.0074 (11) | 0.0020 (10) |
C4 | 0.0540 (14) | 0.0726 (17) | 0.0439 (13) | −0.0127 (13) | 0.0108 (11) | −0.0154 (12) |
C5 | 0.0582 (16) | 0.0783 (19) | 0.0540 (16) | −0.0061 (15) | 0.0139 (13) | −0.0188 (15) |
C6 | 0.0574 (15) | 0.0707 (17) | 0.0393 (13) | −0.0097 (13) | 0.0106 (11) | −0.0129 (12) |
C7 | 0.075 (2) | 0.077 (2) | 0.094 (2) | −0.0218 (17) | 0.0287 (18) | −0.0460 (19) |
C8 | 0.0577 (14) | 0.0429 (12) | 0.0377 (12) | −0.0112 (10) | 0.0137 (10) | −0.0042 (9) |
C9 | 0.0513 (13) | 0.0463 (13) | 0.0378 (12) | −0.0094 (10) | 0.0127 (10) | −0.0067 (10) |
C10 | 0.0568 (15) | 0.0528 (15) | 0.0696 (17) | −0.0138 (13) | 0.0187 (13) | 0.0026 (13) |
C11 | 0.0489 (14) | 0.0617 (17) | 0.0770 (19) | −0.0073 (13) | 0.0155 (13) | −0.0028 (15) |
C12 | 0.0586 (15) | 0.0486 (14) | 0.0508 (14) | 0.0022 (12) | 0.0130 (12) | −0.0080 (11) |
C13 | 0.0627 (16) | 0.0404 (13) | 0.0561 (15) | −0.0085 (11) | 0.0154 (12) | −0.0038 (11) |
C14 | 0.0508 (13) | 0.0483 (14) | 0.0535 (14) | −0.0134 (11) | 0.0094 (11) | −0.0078 (11) |
C15 | 0.0442 (12) | 0.0444 (13) | 0.0545 (14) | −0.0101 (10) | 0.0065 (11) | −0.0092 (11) |
C16 | 0.0443 (13) | 0.0585 (15) | 0.0570 (15) | −0.0075 (11) | 0.0143 (11) | −0.0078 (12) |
C17 | 0.0427 (13) | 0.0572 (15) | 0.0660 (17) | −0.0049 (11) | 0.0072 (12) | −0.0067 (13) |
C18 | 0.0515 (14) | 0.0513 (14) | 0.0556 (15) | −0.0186 (12) | 0.0024 (11) | −0.0074 (12) |
C19 | 0.0559 (15) | 0.0734 (18) | 0.0512 (15) | −0.0132 (14) | 0.0134 (12) | −0.0185 (13) |
C20 | 0.0447 (13) | 0.0622 (16) | 0.0637 (17) | −0.0063 (12) | 0.0102 (12) | −0.0196 (13) |
C21 | 0.0721 (19) | 0.073 (2) | 0.0630 (18) | −0.0216 (16) | −0.0011 (15) | 0.0012 (15) |
N1 | 0.0456 (10) | 0.0468 (11) | 0.0470 (11) | −0.0022 (9) | 0.0058 (8) | −0.0045 (9) |
N2 | 0.0492 (11) | 0.0475 (11) | 0.0360 (10) | −0.0078 (9) | 0.0077 (8) | −0.0040 (8) |
O1 | 0.0800 (15) | 0.0745 (14) | 0.0709 (13) | −0.0191 (11) | 0.0147 (11) | 0.0148 (11) |
O2 | 0.0758 (14) | 0.0482 (11) | 0.0922 (16) | 0.0069 (10) | −0.0034 (12) | −0.0079 (10) |
S1 | 0.0732 (5) | 0.0428 (3) | 0.0751 (5) | −0.0149 (3) | 0.0269 (4) | −0.0054 (3) |
S2 | 0.0555 (4) | 0.0452 (3) | 0.0602 (4) | −0.0057 (3) | 0.0050 (3) | 0.0005 (3) |
Br1 | 0.0770 (3) | 0.0728 (2) | 0.1034 (3) | 0.01559 (17) | 0.0035 (2) | 0.01238 (18) |
Geometric parameters (Å, º) top
C1—N1 | 1.480 (3) | C10—C11 | 1.372 (4) |
C1—C2 | 1.519 (4) | C10—H10 | 0.9300 |
C1—H1A | 0.9700 | C11—C12 | 1.371 (4) |
C1—H1B | 0.9700 | C11—H11 | 0.9300 |
C2—C5 | 1.542 (4) | C12—C13 | 1.366 (4) |
C2—C3 | 1.549 (4) | C12—Br1 | 1.893 (3) |
C2—H2 | 0.9800 | C13—C14 | 1.386 (4) |
C3—N2 | 1.469 (3) | C13—H13 | 0.9300 |
C3—C4 | 1.522 (4) | C14—H14 | 0.9300 |
C3—H3 | 0.9800 | C15—C20 | 1.377 (4) |
C4—N1 | 1.473 (3) | C15—C16 | 1.388 (4) |
C4—H4A | 0.9700 | C15—S2 | 1.763 (3) |
C4—H4B | 0.9700 | C16—C17 | 1.381 (4) |
C5—C6 | 1.510 (4) | C16—H16 | 0.9300 |
C5—H5A | 0.9700 | C17—C18 | 1.385 (4) |
C5—H5B | 0.9700 | C17—H17 | 0.9300 |
C6—N2 | 1.463 (3) | C18—C19 | 1.382 (4) |
C6—C7 | 1.528 (4) | C18—C21 | 1.500 (4) |
C6—H6 | 0.9800 | C19—C20 | 1.381 (4) |
C7—S1 | 1.795 (3) | C19—H19 | 0.9300 |
C7—H7A | 0.9700 | C20—H20 | 0.9300 |
C7—H7B | 0.9700 | C21—H21A | 0.9600 |
C8—N2 | 1.441 (3) | C21—H21B | 0.9600 |
C8—C9 | 1.513 (4) | C21—H21C | 0.9600 |
C8—S1 | 1.869 (2) | N1—S2 | 1.627 (2) |
C8—H8 | 0.9800 | O1—S2 | 1.423 (2) |
C9—C14 | 1.384 (4) | O2—S2 | 1.428 (2) |
C9—C10 | 1.384 (4) | | |
| | | |
N1—C1—C2 | 102.5 (2) | C11—C10—H10 | 119.0 |
N1—C1—H1A | 111.3 | C9—C10—H10 | 119.0 |
C2—C1—H1A | 111.3 | C12—C11—C10 | 118.9 (3) |
N1—C1—H1B | 111.3 | C12—C11—H11 | 120.6 |
C2—C1—H1B | 111.3 | C10—C11—H11 | 120.6 |
H1A—C1—H1B | 109.2 | C13—C12—C11 | 121.1 (3) |
C1—C2—C5 | 113.5 (2) | C13—C12—Br1 | 118.9 (2) |
C1—C2—C3 | 105.2 (2) | C11—C12—Br1 | 119.9 (2) |
C5—C2—C3 | 104.3 (2) | C12—C13—C14 | 119.4 (2) |
C1—C2—H2 | 111.2 | C12—C13—H13 | 120.3 |
C5—C2—H2 | 111.2 | C14—C13—H13 | 120.3 |
C3—C2—H2 | 111.2 | C9—C14—C13 | 120.9 (2) |
N2—C3—C4 | 111.2 (2) | C9—C14—H14 | 119.5 |
N2—C3—C2 | 105.63 (19) | C13—C14—H14 | 119.5 |
C4—C3—C2 | 105.4 (2) | C20—C15—C16 | 120.4 (3) |
N2—C3—H3 | 111.4 | C20—C15—S2 | 119.7 (2) |
C4—C3—H3 | 111.4 | C16—C15—S2 | 119.7 (2) |
C2—C3—H3 | 111.4 | C17—C16—C15 | 119.1 (2) |
N1—C4—C3 | 102.5 (2) | C17—C16—H16 | 120.5 |
N1—C4—H4A | 111.3 | C15—C16—H16 | 120.5 |
C3—C4—H4A | 111.3 | C16—C17—C18 | 121.7 (3) |
N1—C4—H4B | 111.3 | C16—C17—H17 | 119.2 |
C3—C4—H4B | 111.3 | C18—C17—H17 | 119.2 |
H4A—C4—H4B | 109.2 | C19—C18—C17 | 117.8 (3) |
C6—C5—C2 | 104.4 (2) | C19—C18—C21 | 120.7 (3) |
C6—C5—H5A | 110.9 | C17—C18—C21 | 121.6 (3) |
C2—C5—H5A | 110.9 | C20—C19—C18 | 121.9 (3) |
C6—C5—H5B | 110.9 | C20—C19—H19 | 119.1 |
C2—C5—H5B | 110.9 | C18—C19—H19 | 119.1 |
H5A—C5—H5B | 108.9 | C15—C20—C19 | 119.2 (3) |
N2—C6—C5 | 103.1 (2) | C15—C20—H20 | 120.4 |
N2—C6—C7 | 108.1 (2) | C19—C20—H20 | 120.4 |
C5—C6—C7 | 114.1 (3) | C18—C21—H21A | 109.5 |
N2—C6—H6 | 110.4 | C18—C21—H21B | 109.5 |
C5—C6—H6 | 110.4 | H21A—C21—H21B | 109.5 |
C7—C6—H6 | 110.4 | C18—C21—H21C | 109.5 |
C6—C7—S1 | 106.6 (2) | H21A—C21—H21C | 109.5 |
C6—C7—H7A | 110.4 | H21B—C21—H21C | 109.5 |
S1—C7—H7A | 110.4 | C4—N1—C1 | 105.6 (2) |
C6—C7—H7B | 110.4 | C4—N1—S2 | 118.9 (2) |
S1—C7—H7B | 110.4 | C1—N1—S2 | 118.9 (2) |
H7A—C7—H7B | 108.6 | C8—N2—C6 | 109.9 (2) |
N2—C8—C9 | 113.50 (19) | C8—N2—C3 | 115.8 (2) |
N2—C8—S1 | 106.81 (16) | C6—N2—C3 | 107.6 (2) |
C9—C8—S1 | 111.25 (17) | C7—S1—C8 | 92.6 (1) |
N2—C8—H8 | 108.4 | O1—S2—O2 | 120.3 (1) |
C9—C8—H8 | 108.4 | O1—S2—N1 | 106.7 (1) |
S1—C8—H8 | 108.4 | O2—S2—N1 | 106.6 (1) |
C14—C9—C10 | 117.7 (3) | O1—S2—C15 | 108.0 (1) |
C14—C9—C8 | 120.9 (2) | O2—S2—C15 | 108.4 (1) |
C10—C9—C8 | 121.3 (2) | N1—S2—C15 | 106.0 (1) |
C11—C10—C9 | 121.9 (3) | | |
| | | |
N1—C1—C2—C5 | 88.2 (3) | C16—C15—C20—C19 | −1.0 (4) |
N1—C1—C2—C3 | −25.2 (3) | S2—C15—C20—C19 | 173.8 (2) |
C1—C2—C3—N2 | 118.2 (2) | C18—C19—C20—C15 | 0.3 (4) |
C5—C2—C3—N2 | −1.5 (3) | C3—C4—N1—C1 | −42.2 (3) |
C1—C2—C3—C4 | 0.4 (3) | C3—C4—N1—S2 | −178.86 (17) |
C5—C2—C3—C4 | −119.3 (2) | C2—C1—N1—C4 | 42.5 (2) |
N2—C3—C4—N1 | −89.3 (2) | C2—C1—N1—S2 | 179.22 (17) |
C2—C3—C4—N1 | 24.7 (3) | C9—C8—N2—C6 | −89.7 (2) |
C1—C2—C5—C6 | −135.2 (2) | S1—C8—N2—C6 | 33.3 (2) |
C3—C2—C5—C6 | −21.2 (3) | C9—C8—N2—C3 | 148.2 (2) |
C2—C5—C6—N2 | 36.2 (3) | S1—C8—N2—C3 | −88.8 (2) |
C2—C5—C6—C7 | −80.8 (3) | C5—C6—N2—C8 | −165.3 (2) |
N2—C6—C7—S1 | 33.5 (3) | C7—C6—N2—C8 | −44.2 (3) |
C5—C6—C7—S1 | 147.6 (2) | C5—C6—N2—C3 | −38.5 (3) |
N2—C8—C9—C14 | −23.4 (3) | C7—C6—N2—C3 | 82.7 (3) |
S1—C8—C9—C14 | −143.9 (2) | C4—C3—N2—C8 | −98.0 (2) |
N2—C8—C9—C10 | 159.7 (2) | C2—C3—N2—C8 | 148.1 (2) |
S1—C8—C9—C10 | 39.2 (3) | C4—C3—N2—C6 | 138.7 (2) |
C14—C9—C10—C11 | 3.1 (4) | C2—C3—N2—C6 | 24.8 (2) |
C8—C9—C10—C11 | −179.9 (3) | C6—C7—S1—C8 | −12.4 (2) |
C9—C10—C11—C12 | −0.7 (4) | N2—C8—S1—C7 | −11.2 (2) |
C10—C11—C12—C13 | −2.0 (4) | C9—C8—S1—C7 | 113.2 (2) |
C10—C11—C12—Br1 | 174.5 (2) | C4—N1—S2—O1 | −176.0 (2) |
C11—C12—C13—C14 | 2.1 (4) | C1—N1—S2—O1 | 53.0 (2) |
Br1—C12—C13—C14 | −174.40 (19) | C4—N1—S2—O2 | −46.3 (2) |
C10—C9—C14—C13 | −3.0 (4) | C1—N1—S2—O2 | −177.3 (2) |
C8—C9—C14—C13 | −180.0 (2) | C4—N1—S2—C15 | 69.1 (2) |
C12—C13—C14—C9 | 0.4 (4) | C1—N1—S2—C15 | −61.9 (2) |
C20—C15—C16—C17 | 0.8 (4) | C20—C15—S2—O1 | 159.0 (2) |
S2—C15—C16—C17 | −174.1 (2) | C16—C15—S2—O1 | −26.1 (2) |
C15—C16—C17—C18 | 0.2 (4) | C20—C15—S2—O2 | 27.2 (3) |
C16—C17—C18—C19 | −0.9 (4) | C16—C15—S2—O2 | −157.9 (2) |
C16—C17—C18—C21 | 178.5 (3) | C20—C15—S2—N1 | −87.0 (2) |
C17—C18—C19—C20 | 0.7 (4) | C16—C15—S2—N1 | 87.9 (2) |
C21—C18—C19—C20 | −178.8 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7B···Cg1i | 0.97 | 2.73 | 3.632 (4) | 156 |
Symmetry code: (i) −x+1, −y+2, −z+1. |