In the title compound, C
10H
8N
2O
4S, the dihedral angle between the pyrrole and benzene rings is 77.9 (1)°. Intermolecular C—H
O hydrogen bonds stabilize the crystal structure, forming molecular chains extending approximately parallel to the
c axis and stacked along the
b axis.
Supporting information
CCDC reference: 259856
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.053
- wR factor = 0.153
- Data-to-parameter ratio = 18.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for N2
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 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
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: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
N-(
p-Nitrophenylsulfonyl)-1
H-pyrrole
top
Crystal data top
C10H8N2O4S | F(000) = 520 |
Mr = 252.24 | Dx = 1.551 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 12.7169 (17) Å | θ = 15–22° |
b = 7.5317 (13) Å | µ = 0.30 mm−1 |
c = 11.2959 (12) Å | T = 293 K |
β = 93.381 (12)° | Block, light yellow |
V = 1080.0 (3) Å3 | 0.30 × 0.25 × 0.15 mm |
Z = 4 | |
Data collection top
Siemens P4 diffractometer | Rint = 0.020 |
Radiation source: fine-focus sealed tube | θmax = 31.0°, θmin = 1.6° |
Graphite monochromator | h = 0→18 |
Non–profiled w scans | k = 0→10 |
3587 measured reflections | l = −16→16 |
3452 independent reflections | 3 standard reflections every 50 reflections |
2611 reflections with I > 2σ(I) | intensity decay: 1% |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.153 | All H-atom parameters refined |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0643P)2 + 0.3051P] where P = (Fo2 + 2Fc2)/3 |
3452 reflections | (Δ/σ)max < 0.001 |
186 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.32 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 | |
S1 | 0.21249 (4) | 0.17799 (8) | 0.80340 (4) | 0.05858 (17) | |
O1 | 0.4295 (2) | −0.4995 (3) | 1.0996 (3) | 0.1138 (8) | |
O2 | 0.4953 (2) | −0.2833 (4) | 1.2045 (2) | 0.1147 (9) | |
O3 | 0.20572 (15) | 0.1051 (3) | 0.68652 (13) | 0.0818 (5) | |
O4 | 0.25465 (15) | 0.3501 (2) | 0.82688 (19) | 0.0837 (6) | |
N1 | 0.09058 (13) | 0.1815 (2) | 0.84683 (14) | 0.0522 (4) | |
N2 | 0.44010 (17) | −0.3421 (3) | 1.1218 (2) | 0.0771 (6) | |
C1 | 0.00619 (18) | 0.0829 (3) | 0.7976 (2) | 0.0604 (5) | |
C2 | −0.0769 (2) | 0.1161 (4) | 0.8621 (3) | 0.0721 (6) | |
C3 | −0.0450 (2) | 0.2361 (4) | 0.9537 (2) | 0.0732 (7) | |
C4 | 0.0568 (2) | 0.2735 (3) | 0.94458 (19) | 0.0629 (5) | |
C5 | 0.27913 (14) | 0.0255 (3) | 0.89942 (16) | 0.0498 (4) | |
C6 | 0.33044 (16) | 0.0848 (3) | 1.00391 (19) | 0.0557 (4) | |
C7 | 0.38310 (17) | −0.0364 (3) | 1.07753 (19) | 0.0598 (5) | |
C8 | 0.38329 (15) | −0.2120 (3) | 1.04403 (19) | 0.0574 (5) | |
C9 | 0.3326 (2) | −0.2732 (3) | 0.9409 (2) | 0.0680 (6) | |
C10 | 0.28044 (19) | −0.1524 (3) | 0.8673 (2) | 0.0634 (5) | |
H1 | 0.020 (2) | 0.009 (4) | 0.734 (2) | 0.069 (7)* | |
H2 | −0.144 (3) | 0.073 (5) | 0.849 (3) | 0.102 (10)* | |
H3 | −0.086 (3) | 0.285 (4) | 1.011 (3) | 0.096 (10)* | |
H4 | 0.106 (2) | 0.344 (4) | 0.986 (2) | 0.077 (8)* | |
H6 | 0.3309 (18) | 0.206 (3) | 1.025 (2) | 0.063 (7)* | |
H7 | 0.413 (2) | −0.001 (4) | 1.142 (2) | 0.081 (8)* | |
H9 | 0.334 (2) | −0.390 (4) | 0.919 (2) | 0.079 (8)* | |
H10 | 0.245 (2) | −0.189 (4) | 0.797 (2) | 0.077 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0562 (3) | 0.0677 (3) | 0.0512 (3) | −0.0051 (2) | −0.00175 (19) | 0.0095 (2) |
O1 | 0.120 (2) | 0.0782 (14) | 0.143 (2) | 0.0225 (13) | 0.0072 (15) | 0.0291 (14) |
O2 | 0.1032 (16) | 0.125 (2) | 0.1111 (18) | 0.0247 (14) | −0.0348 (14) | 0.0245 (15) |
O3 | 0.0809 (11) | 0.1208 (16) | 0.0437 (8) | 0.0078 (11) | 0.0046 (7) | 0.0063 (9) |
O4 | 0.0742 (11) | 0.0697 (11) | 0.1051 (15) | −0.0192 (8) | −0.0125 (10) | 0.0251 (10) |
N1 | 0.0521 (8) | 0.0564 (9) | 0.0471 (7) | 0.0008 (7) | −0.0066 (6) | −0.0027 (7) |
N2 | 0.0584 (11) | 0.0887 (16) | 0.0849 (15) | 0.0161 (11) | 0.0103 (10) | 0.0231 (12) |
C1 | 0.0604 (12) | 0.0585 (12) | 0.0609 (11) | −0.0054 (9) | −0.0103 (9) | 0.0006 (9) |
C2 | 0.0589 (13) | 0.0688 (14) | 0.0880 (17) | −0.0025 (11) | −0.0015 (12) | 0.0202 (13) |
C3 | 0.0779 (15) | 0.0756 (16) | 0.0673 (14) | 0.0160 (13) | 0.0153 (12) | 0.0148 (12) |
C4 | 0.0760 (14) | 0.0627 (12) | 0.0487 (10) | 0.0090 (11) | −0.0063 (9) | −0.0028 (9) |
C5 | 0.0447 (8) | 0.0566 (10) | 0.0479 (9) | −0.0024 (7) | 0.0004 (7) | −0.0026 (8) |
C8 | 0.0435 (9) | 0.0664 (12) | 0.0627 (11) | 0.0074 (8) | 0.0066 (8) | 0.0068 (9) |
C6 | 0.0543 (10) | 0.0556 (11) | 0.0563 (10) | −0.0020 (8) | −0.0053 (8) | −0.0080 (9) |
C7 | 0.0526 (10) | 0.0736 (14) | 0.0520 (10) | 0.0013 (9) | −0.0065 (8) | −0.0043 (10) |
C9 | 0.0669 (13) | 0.0553 (12) | 0.0815 (15) | 0.0034 (10) | 0.0018 (11) | −0.0110 (11) |
C10 | 0.0655 (12) | 0.0634 (13) | 0.0601 (12) | −0.0009 (10) | −0.0053 (9) | −0.0147 (10) |
Geometric parameters (Å, º) top
S1—N1 | 1.6537 (18) | C5—C10 | 1.389 (3) |
S1—O3 | 1.4277 (18) | C6—C7 | 1.381 (3) |
S1—O4 | 1.4215 (19) | C7—C8 | 1.376 (3) |
S1—C5 | 1.762 (2) | C8—C9 | 1.377 (3) |
N1—C1 | 1.394 (3) | C9—C10 | 1.376 (4) |
N1—C4 | 1.393 (3) | C1—H1 | 0.94 (3) |
N2—O1 | 1.218 (3) | C2—H2 | 0.92 (3) |
N2—O2 | 1.218 (3) | C3—H3 | 0.93 (3) |
N2—C8 | 1.476 (3) | C4—H4 | 0.92 (3) |
C1—C2 | 1.342 (4) | C6—H6 | 0.94 (3) |
C2—C3 | 1.415 (4) | C7—H7 | 0.85 (3) |
C3—C4 | 1.335 (4) | C9—H9 | 0.91 (3) |
C5—C6 | 1.388 (3) | C10—H10 | 0.93 (3) |
| | | |
O3—S1—N1 | 105.90 (10) | C5—C6—H6 | 121.7 (15) |
O3—S1—C5 | 108.63 (11) | C8—C7—C6 | 118.6 (2) |
O4—S1—O3 | 121.64 (13) | C7—C8—C9 | 123.1 (2) |
O4—S1—N1 | 106.26 (11) | C7—C8—N2 | 118.9 (2) |
O4—S1—C5 | 108.47 (10) | C9—C8—N2 | 118.0 (2) |
N1—S1—C5 | 104.66 (9) | C10—C9—C8 | 118.4 (2) |
C1—N1—S1 | 125.90 (16) | C9—C10—C5 | 119.5 (2) |
C4—N1—C1 | 108.4 (2) | C2—C1—H1 | 135.9 (16) |
C4—N1—S1 | 125.58 (16) | N1—C1—H1 | 116.8 (16) |
O1—N2—O2 | 124.3 (3) | C1—C2—H2 | 127 (2) |
O1—N2—C8 | 118.6 (3) | C3—C2—H2 | 125 (2) |
O2—N2—C8 | 117.1 (2) | C4—C3—H3 | 124 (2) |
C2—C1—N1 | 107.2 (2) | C2—C3—H3 | 128 (2) |
C1—C2—C3 | 108.4 (2) | C3—C4—H4 | 135.4 (18) |
C4—C3—C2 | 108.4 (2) | N1—C4—H4 | 116.9 (18) |
C3—C4—N1 | 107.6 (2) | C8—C7—H7 | 122 (2) |
C6—C5—C10 | 121.4 (2) | C6—C7—H7 | 119 (2) |
C6—C5—S1 | 119.90 (16) | C10—C9—H9 | 119.4 (18) |
C10—C5—S1 | 118.74 (16) | C8—C9—H9 | 122.2 (18) |
C7—C6—C5 | 119.1 (2) | C9—C10—H10 | 120.8 (17) |
C7—C6—H6 | 119.2 (15) | C5—C10—H10 | 119.7 (17) |
| | | |
O4—S1—N1—C4 | −35.8 (2) | C7—C8—N2—O1 | 171.1 (2) |
O3—S1—N1—C4 | −166.39 (18) | C9—C8—N2—O1 | −8.8 (3) |
C5—S1—N1—C4 | 78.91 (19) | C7—C8—N2—O2 | −9.2 (3) |
O4—S1—N1—C1 | 149.40 (18) | C9—C8—N2—O2 | 171.0 (3) |
O3—S1—N1—C1 | 18.8 (2) | C6—C5—C10—C9 | 0.7 (4) |
C5—S1—N1—C1 | −95.93 (18) | S1—C5—C10—C9 | 179.63 (19) |
O4—S1—C5—C6 | 21.9 (2) | C4—N1—C1—C2 | 1.0 (2) |
O3—S1—C5—C6 | 155.98 (17) | S1—N1—C1—C2 | 176.61 (16) |
N1—S1—C5—C6 | −91.25 (17) | C1—N1—C4—C3 | −1.3 (2) |
O4—S1—C5—C10 | −157.09 (18) | S1—N1—C4—C3 | −176.85 (17) |
O3—S1—C5—C10 | −23.0 (2) | C5—C10—C9—C8 | −0.8 (4) |
N1—S1—C5—C10 | 89.80 (18) | C7—C8—C9—C10 | 0.8 (4) |
C9—C8—C7—C6 | −0.6 (3) | N2—C8—C9—C10 | −179.3 (2) |
N2—C8—C7—C6 | 179.5 (2) | N1—C1—C2—C3 | −0.4 (3) |
C8—C7—C6—C5 | 0.4 (3) | N1—C4—C3—C2 | 1.0 (3) |
C10—C5—C6—C7 | −0.5 (3) | C1—C2—C3—C4 | −0.4 (3) |
S1—C5—C6—C7 | −179.39 (16) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O3i | 0.93 (3) | 2.56 (2) | 3.359 (3) | 145 (2) |
C9—H9···O4ii | 0.92 (3) | 2.41 (3) | 3.247 (3) | 152 (2) |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, y−1, z. |