In the title compound, C
19H
21BrN
2O
2S, the fused pyrrolidine rings adopt envelope conformations. The molecular packing is stabilized by weak intermolecular C—H
O interactions and van der Waals forces.
Supporting information
CCDC reference: 282300
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.004 Å
- R factor = 0.039
- wR factor = 0.118
- Data-to-parameter ratio = 19.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.15
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.59 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.16 Ratio
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C19 H21 Br N2 O2 S
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 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
2 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
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).
1-(
p-Bromophenyl)-5-tosylperhydropyrrolo[3,4-
b]pyrrole
top
Crystal data top
C19H21BrN2O2S | F(000) = 864 |
Mr = 421.35 | Dx = 1.502 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6484 reflections |
a = 17.7114 (13) Å | θ = 2.3–22.9° |
b = 7.8569 (6) Å | µ = 2.33 mm−1 |
c = 14.3048 (10) Å | T = 273 K |
β = 110.589 (1)° | Block, colourless |
V = 1863.5 (2) Å3 | 0.22 × 0.20 × 0.18 mm |
Z = 4 | |
Data collection top
CCD Area Detector diffractometer | 3239 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.024 |
Graphite monochromator | θmax = 28.0°, θmin = 2.5° |
ω scans | h = −23→22 |
20629 measured reflections | k = −10→10 |
4384 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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0686P)2 + 0.4426P] where P = (Fo2 + 2Fc2)/3 |
4384 reflections | (Δ/σ)max < 0.001 |
227 parameters | Δρmax = 0.99 e Å−3 |
0 restraints | Δρmin = −0.46 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 | 0.160753 (18) | 0.42021 (4) | 0.38803 (2) | 0.07685 (14) | |
S1 | −0.32946 (4) | 0.67737 (8) | −0.20456 (5) | 0.05956 (18) | |
O1 | −0.28156 (12) | 0.8258 (2) | −0.1696 (2) | 0.0845 (7) | |
O2 | −0.36266 (13) | 0.6417 (3) | −0.30903 (14) | 0.0873 (6) | |
N1 | −0.27318 (11) | 0.5161 (2) | −0.15293 (14) | 0.0499 (4) | |
N2 | −0.10371 (11) | 0.3270 (2) | −0.01576 (13) | 0.0472 (4) | |
C1 | −0.6026 (2) | 0.6846 (6) | −0.0447 (3) | 0.1159 (16) | |
H1A | −0.6308 | 0.7912 | −0.0607 | 0.174* | |
H1B | −0.5810 | 0.6706 | 0.0265 | 0.174* | |
H1C | −0.6393 | 0.5932 | −0.0739 | 0.174* | |
C2 | −0.53499 (18) | 0.6828 (4) | −0.0853 (2) | 0.0725 (8) | |
C3 | −0.46513 (19) | 0.7746 (4) | −0.0381 (2) | 0.0782 (8) | |
H3 | −0.4604 | 0.8369 | 0.0191 | 0.094* | |
C4 | −0.40242 (17) | 0.7752 (4) | −0.0745 (2) | 0.0698 (7) | |
H4 | −0.3558 | 0.8372 | −0.0421 | 0.084* | |
C5 | −0.40962 (13) | 0.6832 (3) | −0.15906 (17) | 0.0527 (5) | |
C6 | −0.47893 (15) | 0.5904 (3) | −0.2068 (2) | 0.0588 (6) | |
H6 | −0.4837 | 0.5279 | −0.2638 | 0.071* | |
C7 | −0.54078 (16) | 0.5908 (3) | −0.1697 (2) | 0.0675 (7) | |
H7 | −0.5872 | 0.5282 | −0.2020 | 0.081* | |
C8 | −0.22385 (13) | 0.5196 (3) | −0.04567 (16) | 0.0480 (5) | |
H8A | −0.2568 | 0.5437 | −0.0056 | 0.058* | |
H8B | −0.1815 | 0.6042 | −0.0317 | 0.058* | |
C9 | −0.18839 (13) | 0.3386 (3) | −0.02541 (16) | 0.0457 (5) | |
H9 | −0.1966 | 0.2894 | 0.0332 | 0.055* | |
C10 | −0.23403 (15) | 0.2350 (3) | −0.11977 (18) | 0.0544 (5) | |
H10 | −0.2512 | 0.1247 | −0.1022 | 0.065* | |
C11 | −0.30633 (15) | 0.3438 (3) | −0.17682 (19) | 0.0579 (6) | |
H11A | −0.3242 | 0.3217 | −0.2480 | 0.069* | |
H11B | −0.3509 | 0.3253 | −0.1535 | 0.069* | |
C12 | −0.09204 (16) | 0.2161 (3) | −0.09108 (18) | 0.0586 (6) | |
H12A | −0.0756 | 0.1030 | −0.0645 | 0.070* | |
H12B | −0.0517 | 0.2621 | −0.1155 | 0.070* | |
C13 | −0.17377 (17) | 0.2120 (3) | −0.17258 (19) | 0.0620 (6) | |
H13A | −0.1824 | 0.1042 | −0.2078 | 0.074* | |
H13B | −0.1788 | 0.3033 | −0.2201 | 0.074* | |
C14 | −0.04311 (13) | 0.3521 (3) | 0.07507 (16) | 0.0447 (4) | |
C15 | −0.05725 (15) | 0.4383 (3) | 0.15312 (17) | 0.0506 (5) | |
H15 | −0.1084 | 0.4817 | 0.1430 | 0.061* | |
C16 | 0.00320 (15) | 0.4602 (3) | 0.24485 (18) | 0.0544 (5) | |
H16 | −0.0073 | 0.5173 | 0.2959 | 0.065* | |
C17 | 0.07902 (14) | 0.3966 (3) | 0.25999 (18) | 0.0524 (5) | |
C18 | 0.09551 (14) | 0.3145 (3) | 0.18435 (19) | 0.0550 (5) | |
H18 | 0.1471 | 0.2737 | 0.1950 | 0.066* | |
C19 | 0.03523 (14) | 0.2931 (3) | 0.09278 (18) | 0.0514 (5) | |
H19 | 0.0469 | 0.2383 | 0.0418 | 0.062* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0730 (2) | 0.0644 (2) | 0.0703 (2) | −0.00241 (12) | −0.00331 (14) | 0.00384 (12) |
S1 | 0.0511 (3) | 0.0547 (3) | 0.0655 (4) | 0.0046 (3) | 0.0114 (3) | 0.0153 (3) |
O1 | 0.0595 (11) | 0.0471 (10) | 0.141 (2) | 0.0015 (8) | 0.0279 (12) | 0.0209 (11) |
O2 | 0.0800 (13) | 0.1235 (18) | 0.0535 (11) | 0.0226 (13) | 0.0176 (10) | 0.0257 (12) |
N1 | 0.0488 (10) | 0.0395 (9) | 0.0523 (10) | −0.0010 (8) | 0.0065 (8) | −0.0010 (8) |
N2 | 0.0523 (10) | 0.0430 (9) | 0.0481 (10) | 0.0070 (8) | 0.0199 (8) | −0.0004 (7) |
C1 | 0.101 (3) | 0.154 (4) | 0.111 (3) | 0.054 (3) | 0.060 (2) | 0.064 (3) |
C2 | 0.0675 (17) | 0.0808 (19) | 0.0687 (17) | 0.0294 (15) | 0.0232 (14) | 0.0300 (15) |
C3 | 0.0782 (19) | 0.096 (2) | 0.0488 (14) | 0.0298 (17) | 0.0073 (13) | −0.0015 (14) |
C4 | 0.0585 (15) | 0.0674 (16) | 0.0629 (15) | 0.0082 (12) | −0.0044 (12) | −0.0098 (12) |
C5 | 0.0456 (11) | 0.0484 (12) | 0.0519 (12) | 0.0054 (9) | 0.0017 (9) | 0.0047 (9) |
C6 | 0.0481 (13) | 0.0585 (14) | 0.0583 (14) | 0.0028 (10) | 0.0044 (10) | −0.0051 (10) |
C7 | 0.0507 (14) | 0.0596 (15) | 0.0832 (19) | 0.0040 (11) | 0.0124 (13) | 0.0120 (13) |
C8 | 0.0460 (11) | 0.0406 (10) | 0.0511 (12) | 0.0018 (9) | 0.0094 (9) | −0.0048 (9) |
C9 | 0.0527 (12) | 0.0369 (10) | 0.0485 (11) | 0.0017 (9) | 0.0189 (9) | 0.0017 (8) |
C10 | 0.0661 (14) | 0.0354 (10) | 0.0599 (13) | −0.0086 (10) | 0.0200 (11) | −0.0057 (9) |
C11 | 0.0572 (13) | 0.0497 (13) | 0.0593 (14) | −0.0132 (10) | 0.0114 (11) | −0.0129 (10) |
C12 | 0.0730 (16) | 0.0494 (12) | 0.0594 (14) | 0.0094 (11) | 0.0308 (12) | −0.0040 (10) |
C13 | 0.0800 (17) | 0.0502 (13) | 0.0556 (13) | 0.0000 (12) | 0.0233 (12) | −0.0125 (11) |
C14 | 0.0519 (11) | 0.0363 (10) | 0.0486 (11) | 0.0029 (8) | 0.0208 (9) | 0.0062 (8) |
C15 | 0.0521 (12) | 0.0482 (12) | 0.0521 (12) | 0.0102 (9) | 0.0190 (10) | 0.0020 (9) |
C16 | 0.0624 (14) | 0.0475 (11) | 0.0520 (12) | 0.0057 (10) | 0.0188 (11) | 0.0009 (10) |
C17 | 0.0523 (12) | 0.0423 (11) | 0.0563 (13) | −0.0027 (9) | 0.0111 (10) | 0.0068 (9) |
C18 | 0.0456 (12) | 0.0483 (12) | 0.0711 (15) | 0.0010 (9) | 0.0204 (11) | 0.0069 (11) |
C19 | 0.0537 (12) | 0.0472 (11) | 0.0607 (13) | 0.0037 (9) | 0.0292 (11) | 0.0027 (10) |
Geometric parameters (Å, º) top
Br1—C17 | 1.903 (2) | C8—H8A | 0.9700 |
S1—O1 | 1.425 (2) | C8—H8B | 0.9700 |
S1—O2 | 1.428 (2) | C9—C10 | 1.540 (3) |
S1—N1 | 1.621 (2) | C9—H9 | 0.9800 |
S1—C5 | 1.758 (3) | C10—C11 | 1.517 (3) |
N1—C11 | 1.468 (3) | C10—C13 | 1.520 (4) |
N1—C8 | 1.475 (3) | C10—H10 | 0.9800 |
N2—C14 | 1.378 (3) | C11—H11A | 0.9700 |
N2—C12 | 1.455 (3) | C11—H11B | 0.9700 |
N2—C9 | 1.460 (3) | C12—C13 | 1.506 (4) |
C1—C2 | 1.505 (5) | C12—H12A | 0.9700 |
C1—H1A | 0.9600 | C12—H12B | 0.9700 |
C1—H1B | 0.9600 | C13—H13A | 0.9700 |
C1—H1C | 0.9600 | C13—H13B | 0.9700 |
C2—C7 | 1.379 (4) | C14—C19 | 1.399 (3) |
C2—C3 | 1.386 (5) | C14—C15 | 1.402 (3) |
C3—C4 | 1.383 (4) | C15—C16 | 1.382 (3) |
C3—H3 | 0.9300 | C15—H15 | 0.9300 |
C4—C5 | 1.377 (4) | C16—C17 | 1.376 (4) |
C4—H4 | 0.9300 | C16—H16 | 0.9300 |
C5—C6 | 1.384 (3) | C17—C18 | 1.376 (4) |
C6—C7 | 1.375 (4) | C18—C19 | 1.379 (3) |
C6—H6 | 0.9300 | C18—H18 | 0.9300 |
C7—H7 | 0.9300 | C19—H19 | 0.9300 |
C8—C9 | 1.540 (3) | | |
| | | |
O1—S1—O2 | 120.2 (2) | N2—C9—H9 | 110.6 |
O1—S1—N1 | 106.6 (1) | C8—C9—H9 | 110.6 |
O2—S1—N1 | 106.5 (1) | C10—C9—H9 | 110.6 |
O1—S1—C5 | 107.9 (1) | C11—C10—C13 | 114.0 (2) |
O2—S1—C5 | 107.7 (1) | C11—C10—C9 | 104.91 (18) |
N1—S1—C5 | 107.4 (1) | C13—C10—C9 | 104.75 (19) |
C11—N1—C8 | 107.5 (2) | C11—C10—H10 | 110.9 |
C11—N1—S1 | 118.9 (2) | C13—C10—H10 | 110.9 |
C8—N1—S1 | 120.3 (1) | C9—C10—H10 | 110.9 |
C14—N2—C12 | 121.2 (2) | N1—C11—C10 | 101.63 (18) |
C14—N2—C9 | 120.9 (2) | N1—C11—H11A | 111.4 |
C12—N2—C9 | 112.1 (2) | C10—C11—H11A | 111.4 |
C2—C1—H1A | 109.5 | N1—C11—H11B | 111.4 |
C2—C1—H1B | 109.5 | C10—C11—H11B | 111.4 |
H1A—C1—H1B | 109.5 | H11A—C11—H11B | 109.3 |
C2—C1—H1C | 109.5 | N2—C12—C13 | 103.75 (19) |
H1A—C1—H1C | 109.5 | N2—C12—H12A | 111.0 |
H1B—C1—H1C | 109.5 | C13—C12—H12A | 111.0 |
C7—C2—C3 | 118.6 (3) | N2—C12—H12B | 111.0 |
C7—C2—C1 | 121.3 (3) | C13—C12—H12B | 111.0 |
C3—C2—C1 | 120.1 (3) | H12A—C12—H12B | 109.0 |
C4—C3—C2 | 121.0 (3) | C12—C13—C10 | 105.3 (2) |
C4—C3—H3 | 119.5 | C12—C13—H13A | 110.7 |
C2—C3—H3 | 119.5 | C10—C13—H13A | 110.7 |
C5—C4—C3 | 119.4 (3) | C12—C13—H13B | 110.7 |
C5—C4—H4 | 120.3 | C10—C13—H13B | 110.7 |
C3—C4—H4 | 120.3 | H13A—C13—H13B | 108.8 |
C4—C5—C6 | 120.2 (3) | N2—C14—C19 | 121.16 (19) |
C4—C5—S1 | 120.13 (19) | N2—C14—C15 | 121.48 (19) |
C6—C5—S1 | 119.67 (19) | C19—C14—C15 | 117.4 (2) |
C7—C6—C5 | 119.8 (2) | C16—C15—C14 | 121.4 (2) |
C7—C6—H6 | 120.1 | C16—C15—H15 | 119.3 |
C5—C6—H6 | 120.1 | C14—C15—H15 | 119.3 |
C6—C7—C2 | 121.0 (3) | C17—C16—C15 | 119.4 (2) |
C6—C7—H7 | 119.5 | C17—C16—H16 | 120.3 |
C2—C7—H7 | 119.5 | C15—C16—H16 | 120.3 |
N1—C8—C9 | 103.42 (16) | C18—C17—C16 | 120.7 (2) |
N1—C8—H8A | 111.1 | C18—C17—Br1 | 120.16 (18) |
C9—C8—H8A | 111.1 | C16—C17—Br1 | 119.09 (19) |
N1—C8—H8B | 111.1 | C17—C18—C19 | 119.8 (2) |
C9—C8—H8B | 111.1 | C17—C18—H18 | 120.1 |
H8A—C8—H8B | 109.0 | C19—C18—H18 | 120.1 |
N2—C9—C8 | 114.40 (17) | C18—C19—C14 | 121.3 (2) |
N2—C9—C10 | 104.76 (17) | C18—C19—H19 | 119.4 |
C8—C9—C10 | 105.63 (17) | C14—C19—H19 | 119.4 |
| | | |
O1—S1—N1—C11 | −178.9 (2) | N1—C8—C9—C10 | −10.7 (2) |
O2—S1—N1—C11 | −49.4 (2) | N2—C9—C10—C11 | −135.41 (18) |
C5—S1—N1—C11 | 65.72 (19) | C8—C9—C10—C11 | −14.3 (2) |
O1—S1—N1—C8 | 45.0 (2) | N2—C9—C10—C13 | −15.0 (2) |
O2—S1—N1—C8 | 174.46 (18) | C8—C9—C10—C13 | 106.1 (2) |
C5—S1—N1—C8 | −70.40 (19) | C8—N1—C11—C10 | −42.4 (2) |
C7—C2—C3—C4 | 0.2 (4) | S1—N1—C11—C10 | 176.43 (16) |
C1—C2—C3—C4 | −179.7 (3) | C13—C10—C11—N1 | −80.3 (2) |
C2—C3—C4—C5 | 0.1 (4) | C9—C10—C11—N1 | 33.7 (2) |
C3—C4—C5—C6 | −0.3 (4) | C14—N2—C12—C13 | 174.90 (19) |
C3—C4—C5—S1 | −178.2 (2) | C9—N2—C12—C13 | 21.6 (2) |
O1—S1—C5—C4 | −24.0 (2) | N2—C12—C13—C10 | −30.2 (2) |
O2—S1—C5—C4 | −155.1 (2) | C11—C10—C13—C12 | 142.2 (2) |
N1—S1—C5—C4 | 90.5 (2) | C9—C10—C13—C12 | 28.1 (2) |
O1—S1—C5—C6 | 158.13 (19) | C12—N2—C14—C19 | 9.6 (3) |
O2—S1—C5—C6 | 27.0 (2) | C9—N2—C14—C19 | 160.64 (19) |
N1—S1—C5—C6 | −87.3 (2) | C12—N2—C14—C15 | −170.7 (2) |
C4—C5—C6—C7 | 0.3 (4) | C9—N2—C14—C15 | −19.7 (3) |
S1—C5—C6—C7 | 178.14 (19) | N2—C14—C15—C16 | 178.6 (2) |
C5—C6—C7—C2 | 0.1 (4) | C19—C14—C15—C16 | −1.7 (3) |
C3—C2—C7—C6 | −0.3 (4) | C14—C15—C16—C17 | 0.3 (4) |
C1—C2—C7—C6 | 179.7 (3) | C15—C16—C17—C18 | 1.2 (4) |
C11—N1—C8—C9 | 33.4 (2) | C15—C16—C17—Br1 | −177.74 (17) |
S1—N1—C8—C9 | 173.87 (14) | C16—C17—C18—C19 | −1.0 (4) |
C14—N2—C9—C8 | 87.3 (2) | Br1—C17—C18—C19 | 177.87 (17) |
C12—N2—C9—C8 | −119.3 (2) | C17—C18—C19—C14 | −0.5 (3) |
C14—N2—C9—C10 | −157.47 (18) | N2—C14—C19—C18 | −178.5 (2) |
C12—N2—C9—C10 | −4.1 (2) | C15—C14—C19—C18 | 1.9 (3) |
N1—C8—C9—N2 | 104.0 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O2i | 0.93 | 2.47 | 3.206 (3) | 137 |
C10—H10···O1ii | 0.98 | 2.52 | 3.337 (3) | 140 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, y−1, z. |