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The structure of the title compound, C12H14N2O4S2, has been determined as part of an investigation into the structure and substitution patterns in benzene­sulfonyl-protected pyrroles. The pyrrole N atom is in a near-planar bonding environment, with an angle between the S-N bond and the mean plane of the pyrrole ring of 1.72 (10)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806004132/fl2003sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806004132/fl2003Isup2.hkl
Contains datablock I

CCDC reference: 601164

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.047
  • wR factor = 0.109
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.754 0.920 Tmin(prime) and Tmax expected: 0.902 0.918 RR(prime) = 0.835 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.83
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: OSCAIL (McArdle, 1995) and PLATON (Spek, 2003).

N,N-Dimethyl-1-phenylsulfonyl-1H-pyrrole-3-sulfonamide top
Crystal data top
C12H14N2O4S2F(000) = 656
Mr = 314.37Dx = 1.464 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5103 reflections
a = 8.1322 (7) Åθ = 2.2–28.3°
b = 11.1027 (9) ŵ = 0.39 mm1
c = 16.0757 (14) ÅT = 173 K
β = 100.680 (2)°Block, colourless
V = 1426.3 (2) Å30.26 × 0.22 × 0.22 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3534 independent reflections
Radiation source: fine-focus sealed tube3357 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ω scansθmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS in SAINT-Plus; Bruker, 2003)
h = 1010
Tmin = 0.754, Tmax = 0.92k = 1414
15246 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: difference Fourier map
wR(F2) = 0.109All H-atom parameters refined
S = 1.20 w = 1/[σ2(Fo2) + (0.0424P)2 + 1.2568P]
where P = (Fo2 + 2Fc2)/3
3534 reflections(Δ/σ)max < 0.001
237 parametersΔρmax = 0.52 e Å3
0 restraintsΔρmin = 0.30 e Å3
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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

6.1806 (0.0054) x - 6.1783 (0.0093) y + 3.0396 (0.0162) z = 4.0526 (0.0072)

* 0.0058 (0.0012) N1 * -0.0047 (0.0012) C2 * 0.0018 (0.0012) C3 * 0.0018 (0.0013) C4 * -0.0047 (0.0012) C5

Rms deviation of fitted atoms = 0.0041

- 0.9721 (0.0071) x + 7.3615 (0.0076) y + 12.0299 (0.0098) z = 1.1592 (0.0038)

Angle to previous plane (with approximate e.s.d.) = 77.78 (0.07)

* -0.0027 (0.0014) C8 * 0.0102 (0.0014) C9 * -0.0082 (0.0015) C10 * -0.0015 (0.0016) C11 * 0.0091 (0.0017) C12 * -0.0069 (0.0016) C13

Rms deviation of fitted atoms = 0.0072

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
xyzUiso*/Ueq
S10.76003 (6)0.14377 (4)0.06525 (3)0.01749 (13)
S21.12146 (6)0.53927 (4)0.18637 (3)0.01793 (13)
O10.74294 (18)0.04472 (13)0.11930 (9)0.0236 (3)
O31.12617 (18)0.57871 (13)0.10194 (9)0.0242 (3)
O41.07297 (19)0.62177 (13)0.24590 (10)0.0267 (3)
N10.8467 (2)0.25417 (15)0.13011 (10)0.0180 (3)
O20.86055 (17)0.13591 (14)0.00161 (9)0.0242 (3)
N21.3090 (2)0.49114 (15)0.22630 (10)0.0203 (3)
C80.5610 (2)0.19798 (18)0.02032 (12)0.0181 (4)
C30.9852 (2)0.41716 (17)0.17857 (12)0.0174 (4)
C90.4222 (2)0.14403 (19)0.04319 (13)0.0215 (4)
C50.8208 (2)0.27053 (19)0.21248 (12)0.0213 (4)
C20.9465 (2)0.34516 (17)0.10874 (12)0.0180 (4)
C40.9060 (3)0.37005 (19)0.24382 (13)0.0215 (4)
C120.3880 (3)0.3310 (2)0.07406 (14)0.0309 (5)
C110.2481 (3)0.2764 (2)0.05285 (14)0.0285 (5)
C100.2645 (3)0.1832 (2)0.00492 (15)0.0260 (4)
C61.3342 (3)0.4506 (2)0.31501 (14)0.0301 (5)
C130.5469 (3)0.2912 (2)0.03821 (13)0.0254 (4)
C71.3836 (3)0.4085 (2)0.17229 (15)0.0275 (5)
H40.909 (3)0.401 (2)0.2954 (15)0.023 (6)*
H7B1.360 (3)0.435 (2)0.1139 (16)0.023 (6)*
H20.974 (3)0.351 (2)0.0543 (16)0.022 (6)*
H90.439 (3)0.086 (2)0.0823 (16)0.026 (6)*
H50.749 (3)0.216 (2)0.2350 (15)0.025 (6)*
H100.169 (3)0.148 (2)0.0193 (17)0.032 (7)*
H130.637 (4)0.324 (2)0.0526 (17)0.034 (7)*
H6B1.292 (3)0.511 (3)0.3475 (17)0.032 (7)*
H6A1.278 (4)0.373 (3)0.3226 (18)0.042 (8)*
H7C1.502 (4)0.407 (3)0.1948 (18)0.044 (8)*
H7A1.337 (3)0.326 (3)0.1725 (17)0.033 (7)*
H110.142 (4)0.302 (3)0.0781 (17)0.036 (7)*
H120.374 (4)0.398 (3)0.1135 (19)0.043 (8)*
H6C1.450 (4)0.442 (3)0.3323 (17)0.036 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0147 (2)0.0182 (2)0.0196 (2)0.00135 (16)0.00309 (16)0.00319 (17)
S20.0193 (2)0.0140 (2)0.0201 (2)0.00067 (16)0.00272 (17)0.00041 (17)
O10.0218 (7)0.0199 (7)0.0285 (8)0.0007 (6)0.0029 (6)0.0015 (6)
O30.0243 (7)0.0230 (7)0.0251 (7)0.0003 (6)0.0038 (6)0.0069 (6)
O40.0294 (8)0.0188 (7)0.0328 (8)0.0000 (6)0.0082 (6)0.0069 (6)
N10.0185 (7)0.0196 (8)0.0156 (7)0.0030 (6)0.0025 (6)0.0020 (6)
O20.0193 (7)0.0298 (8)0.0244 (7)0.0025 (6)0.0067 (6)0.0094 (6)
N20.0185 (8)0.0199 (8)0.0211 (8)0.0008 (6)0.0002 (6)0.0012 (6)
C80.0148 (8)0.0206 (9)0.0185 (9)0.0010 (7)0.0023 (7)0.0038 (7)
C30.0169 (8)0.0173 (8)0.0178 (9)0.0006 (7)0.0027 (7)0.0008 (7)
C90.0195 (9)0.0208 (9)0.0243 (10)0.0002 (7)0.0048 (7)0.0012 (8)
C50.0220 (9)0.0249 (10)0.0179 (9)0.0026 (8)0.0062 (7)0.0004 (8)
C20.0171 (8)0.0200 (9)0.0171 (9)0.0011 (7)0.0031 (7)0.0015 (7)
C40.0255 (10)0.0237 (10)0.0163 (9)0.0026 (8)0.0062 (7)0.0032 (7)
C120.0334 (12)0.0323 (12)0.0247 (11)0.0020 (9)0.0006 (9)0.0064 (9)
C110.0211 (10)0.0349 (12)0.0268 (11)0.0066 (9)0.0026 (8)0.0053 (9)
C100.0163 (9)0.0296 (11)0.0322 (11)0.0009 (8)0.0049 (8)0.0043 (9)
C60.0274 (11)0.0394 (13)0.0204 (10)0.0004 (10)0.0039 (8)0.0017 (9)
C130.0238 (10)0.0296 (11)0.0227 (10)0.0041 (8)0.0038 (8)0.0036 (8)
C70.0262 (11)0.0261 (11)0.0305 (11)0.0073 (9)0.0061 (9)0.0009 (9)
Geometric parameters (Å, º) top
S1—O11.4243 (15)C5—C41.351 (3)
S1—O21.4255 (14)C5—H50.96 (3)
S1—N11.6775 (16)C2—H20.94 (2)
S1—C81.7524 (19)C4—H40.90 (2)
S2—O41.4318 (15)C12—C131.386 (3)
S2—O31.4335 (15)C12—C111.386 (3)
S2—N21.6309 (17)C12—H120.97 (3)
S2—C31.7409 (19)C11—C101.380 (3)
N1—C21.378 (2)C11—H110.93 (3)
N1—C51.391 (2)C10—H100.94 (3)
N2—C71.470 (3)C6—H6B0.95 (3)
N2—C61.473 (3)C6—H6A1.00 (3)
C8—C91.386 (3)C6—H6C0.94 (3)
C8—C131.389 (3)C13—H130.89 (3)
C3—C21.366 (3)C7—H7B0.97 (2)
C3—C41.428 (3)C7—H7C0.96 (3)
C9—C101.386 (3)C7—H7A0.99 (3)
C9—H90.90 (3)
O1—S1—O2121.63 (9)C3—C2—N1106.29 (16)
O1—S1—N1105.21 (8)C3—C2—H2131.6 (15)
O2—S1—N1105.07 (8)N1—C2—H2122.1 (15)
O1—S1—C8109.24 (9)C5—C4—C3107.18 (17)
O2—S1—C8109.51 (9)C5—C4—H4126.1 (16)
N1—S1—C8104.77 (9)C3—C4—H4126.7 (16)
O4—S2—O3119.76 (9)C13—C12—C11120.2 (2)
O4—S2—N2107.45 (9)C13—C12—H12120.5 (17)
O3—S2—N2106.59 (9)C11—C12—H12119.4 (17)
O4—S2—C3107.21 (9)C10—C11—C12120.8 (2)
O3—S2—C3107.34 (9)C10—C11—H11119.5 (17)
N2—S2—C3108.03 (9)C12—C11—H11119.7 (17)
C2—N1—C5109.96 (16)C11—C10—C9120.0 (2)
C2—N1—S1125.42 (13)C11—C10—H10120.0 (16)
C5—N1—S1124.53 (14)C9—C10—H10120.0 (16)
C7—N2—C6112.49 (18)N2—C6—H6B108.4 (16)
C7—N2—S2115.50 (14)N2—C6—H6A113.5 (17)
C6—N2—S2115.69 (14)H6B—C6—H6A109 (2)
C9—C8—C13122.18 (18)N2—C6—H6C105.7 (17)
C9—C8—S1118.52 (15)H6B—C6—H6C111 (2)
C13—C8—S1119.28 (15)H6A—C6—H6C109 (2)
C2—C3—C4108.83 (17)C12—C13—C8118.2 (2)
C2—C3—S2124.14 (15)C12—C13—H13120.7 (18)
C4—C3—S2126.88 (15)C8—C13—H13121.1 (18)
C8—C9—C10118.6 (2)N2—C7—H7B110.8 (15)
C8—C9—H9118.5 (16)N2—C7—H7C106.3 (18)
C10—C9—H9122.9 (16)H7B—C7—H7C112 (2)
C4—C5—N1107.72 (17)N2—C7—H7A112.1 (16)
C4—C5—H5133.1 (15)H7B—C7—H7A106 (2)
N1—C5—H5119.2 (15)H7C—C7—H7A110 (2)
O1—S1—N1—C2152.01 (16)O4—S2—C3—C431.5 (2)
O2—S1—N1—C222.53 (18)O3—S2—C3—C4161.35 (17)
C8—S1—N1—C292.85 (17)N2—S2—C3—C484.05 (19)
O1—S1—N1—C531.49 (18)C13—C8—C9—C101.3 (3)
O2—S1—N1—C5160.97 (16)S1—C8—C9—C10177.20 (16)
C8—S1—N1—C583.65 (17)C2—N1—C5—C41.1 (2)
O4—S2—N2—C7177.60 (15)S1—N1—C5—C4178.02 (15)
O3—S2—N2—C748.07 (17)C4—C3—C2—N10.6 (2)
C3—S2—N2—C767.02 (17)S2—C3—C2—N1175.20 (14)
O4—S2—N2—C647.99 (18)C5—N1—C2—C31.0 (2)
O3—S2—N2—C6177.53 (16)S1—N1—C2—C3177.97 (14)
C3—S2—N2—C667.38 (17)N1—C5—C4—C30.6 (2)
O1—S1—C8—C91.74 (19)C2—C3—C4—C50.0 (2)
O2—S1—C8—C9137.21 (16)S2—C3—C4—C5175.69 (15)
N1—S1—C8—C9110.55 (16)C13—C12—C11—C101.0 (4)
O1—S1—C8—C13176.78 (16)C12—C11—C10—C90.7 (3)
O2—S1—C8—C1341.32 (19)C8—C9—C10—C111.8 (3)
N1—S1—C8—C1370.93 (18)C11—C12—C13—C81.5 (3)
O4—S2—C3—C2153.46 (17)C9—C8—C13—C120.3 (3)
O3—S2—C3—C223.6 (2)S1—C8—C13—C12178.80 (17)
N2—S2—C3—C291.01 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O1i0.89 (2)2.57 (2)3.325 (3)143 (2)
C6—H6B···O40.95 (3)2.51 (3)2.913 (3)105.9 (19)
C7—H7B···O30.97 (3)2.46 (2)2.891 (3)106.5 (17)
C9—H9···O10.89 (2)2.48 (2)2.887 (2)108.6 (19)
C10—H10···O2ii0.94 (2)2.48 (3)3.317 (3)150 (2)
C11—H11···O3iii0.93 (3)2.52 (3)3.404 (3)160 (2)
C13—H13···O3iv0.89 (3)2.46 (3)3.349 (3)176 (2)
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x1, y, z; (iii) x+1, y+1, z; (iv) x+2, y+1, z.
 

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