2,5-Dimethyl-1-phenyl-sulfonyl-1H-pyrrole-3,4-dicarbaldehyde.

In the title compound, C(14)H(13)NO(4)S, the mean planes of the pyrrole and phenyl rings form a dihedral angle of 88.7 (1)°. The aldehyde groups are slightly twisted from the pyrrole plane. In the crystal structure, mol-ecules are linked into a three-dimensional framework by C-H⋯O hydrogen bonds.

Related literature

For general background, see: Ali et al. (1989 ▶); Amal Raj et al. (2003 ▶). For bond-length data, see: Allen et al. (1987 ▶). For N-atom hybridization details, see: Beddoes et al. (1986 ▶).

Experimental

Crystal data

C14H13NO4S

M = 291.31

Monoclinic,

a = 9.0257 (3) Å

b = 12.6240 (5) Å

c = 11.9914 (5) Å

β = 97.700 (2)°

V = 1353.99 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.940, T max = 0.952

19609 measured reflections

4736 independent reflections

3164 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.154

S = 1.00

4736 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809004425/wn2307sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004425/wn2307Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H13NO4S	F(000) = 608
Mr = 291.31	Dx = 1.429 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.0257 (3) Å	Cell parameters from 6814 reflections
b = 12.6240 (5) Å	θ = 2.4–32.2°
c = 11.9914 (5) Å	µ = 0.25 mm−1
β = 97.700 (2)°	T = 293 K
V = 1353.99 (9) Å3	Block, colourless
Z = 4	0.25 × 0.20 × 0.20 mm

Bruker Kappa-APEXII area-detector diffractometer	4736 independent reflections
Radiation source: fine-focus sealed tube	3164 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω scans	θmax = 32.2°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −13→10
Tmin = 0.940, Tmax = 0.952	k = −18→18
19609 measured reflections	l = −16→17

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0787P)2 + 0.2246P] where P = (Fo2 + 2Fc2)/3
4736 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.42 e Å−3

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
S1	0.51190 (5)	0.21083 (3)	0.25629 (3)	0.05026 (14)
N	0.56878 (14)	0.29263 (9)	0.36572 (10)	0.0417 (3)
O1	0.64275 (15)	0.17150 (11)	0.21659 (11)	0.0704 (4)
O3	0.82639 (16)	0.54763 (12)	0.58440 (12)	0.0777 (4)
O2	0.40939 (17)	0.13956 (10)	0.29555 (12)	0.0743 (4)
O4	0.49857 (19)	0.36086 (17)	0.70677 (12)	0.1023 (6)
C1	0.51247 (15)	0.29778 (11)	0.46937 (11)	0.0422 (3)
C2	0.59280 (15)	0.37280 (11)	0.53213 (11)	0.0404 (3)
C3	0.69918 (14)	0.41747 (11)	0.46621 (11)	0.0383 (3)
C4	0.68371 (15)	0.36717 (11)	0.36473 (11)	0.0412 (3)
C5	0.80621 (18)	0.50177 (13)	0.49571 (14)	0.0524 (4)
H5	0.8646	0.5223	0.4412	0.063*
C6	0.57651 (19)	0.40278 (16)	0.64774 (13)	0.0579 (4)
H6	0.6327	0.4602	0.6779	0.069*
C7	0.3863 (2)	0.23246 (17)	0.50008 (16)	0.0661 (5)
H7A	0.3587	0.2571	0.5702	0.099*
H7B	0.4168	0.1597	0.5075	0.099*
H7C	0.3022	0.2386	0.4423	0.099*
C8	0.7684 (2)	0.38292 (17)	0.26769 (14)	0.0662 (5)
H8A	0.8349	0.4421	0.2825	0.099*
H8B	0.6997	0.3965	0.2009	0.099*
H8C	0.8253	0.3203	0.2571	0.099*
C9	0.41822 (17)	0.29562 (12)	0.15557 (12)	0.0455 (3)
C10	0.4612 (2)	0.29939 (16)	0.04944 (14)	0.0604 (4)
H10	0.5403	0.2583	0.0315	0.072*
C11	0.3837 (3)	0.3659 (2)	−0.02973 (16)	0.0767 (6)
H11	0.4104	0.3696	−0.1019	0.092*
C12	0.2683 (3)	0.42608 (17)	−0.00229 (17)	0.0780 (6)
H12	0.2176	0.4707	−0.0561	0.094*
C13	0.2260 (3)	0.42188 (16)	0.10310 (18)	0.0744 (6)
H13	0.1476	0.4638	0.1207	0.089*
C14	0.3000 (2)	0.35534 (13)	0.18281 (14)	0.0579 (4)
H14	0.2708	0.3507	0.2541	0.069*

	U11	U22	U33	U12	U13	U23
S1	0.0664 (3)	0.0385 (2)	0.0462 (2)	−0.00334 (15)	0.00855 (17)	−0.00739 (14)
N	0.0513 (6)	0.0408 (6)	0.0347 (5)	−0.0058 (5)	0.0120 (5)	−0.0013 (4)
O1	0.0800 (8)	0.0655 (8)	0.0655 (8)	0.0209 (7)	0.0084 (6)	−0.0213 (6)
O3	0.0858 (9)	0.0823 (10)	0.0652 (8)	−0.0240 (7)	0.0105 (7)	−0.0272 (7)
O2	0.1039 (10)	0.0500 (7)	0.0681 (8)	−0.0305 (7)	0.0080 (7)	0.0000 (6)
O4	0.1016 (12)	0.1637 (17)	0.0496 (8)	−0.0353 (11)	0.0398 (8)	−0.0136 (9)
C1	0.0459 (7)	0.0463 (7)	0.0362 (6)	−0.0003 (5)	0.0121 (5)	0.0061 (5)
C2	0.0429 (6)	0.0467 (7)	0.0333 (6)	0.0049 (5)	0.0115 (5)	0.0032 (5)
C3	0.0418 (6)	0.0389 (7)	0.0347 (6)	0.0024 (5)	0.0074 (5)	0.0024 (5)
C4	0.0465 (7)	0.0430 (7)	0.0358 (6)	−0.0019 (5)	0.0123 (5)	0.0015 (5)
C5	0.0560 (8)	0.0535 (9)	0.0480 (8)	−0.0081 (7)	0.0078 (6)	−0.0012 (7)
C6	0.0595 (9)	0.0796 (12)	0.0366 (7)	0.0025 (8)	0.0143 (6)	−0.0055 (7)
C7	0.0662 (10)	0.0772 (12)	0.0595 (10)	−0.0208 (9)	0.0248 (8)	0.0053 (9)
C8	0.0784 (12)	0.0817 (13)	0.0445 (9)	−0.0255 (10)	0.0295 (8)	−0.0068 (8)
C9	0.0551 (8)	0.0435 (7)	0.0379 (7)	−0.0089 (6)	0.0067 (6)	−0.0098 (5)
C10	0.0643 (10)	0.0774 (12)	0.0411 (8)	−0.0095 (8)	0.0134 (7)	−0.0091 (8)
C11	0.0942 (15)	0.0952 (16)	0.0402 (9)	−0.0202 (12)	0.0072 (9)	0.0005 (9)
C12	0.1054 (16)	0.0665 (12)	0.0567 (11)	−0.0007 (11)	−0.0086 (11)	0.0022 (9)
C13	0.0900 (14)	0.0586 (11)	0.0710 (12)	0.0162 (10)	−0.0029 (10)	−0.0134 (9)
C14	0.0742 (11)	0.0527 (9)	0.0472 (9)	0.0036 (8)	0.0099 (8)	−0.0136 (7)

S1—O2	1.4155 (13)	C7—H7A	0.9600
S1—O1	1.4209 (13)	C7—H7B	0.9600
S1—N	1.6945 (12)	C7—H7C	0.9600
S1—C9	1.7452 (17)	C8—H8A	0.9600
N—C4	1.4018 (17)	C8—H8B	0.9600
N—C1	1.4060 (17)	C8—H8C	0.9600
O3—C5	1.203 (2)	C9—C10	1.380 (2)
O4—C6	1.187 (2)	C9—C14	1.381 (2)
C1—C2	1.358 (2)	C10—C11	1.385 (3)
C1—C7	1.492 (2)	C10—H10	0.9300
C2—C3	1.4382 (18)	C11—C12	1.364 (3)
C2—C6	1.463 (2)	C11—H11	0.9300
C3—C4	1.3631 (19)	C12—C13	1.370 (3)
C3—C5	1.449 (2)	C12—H12	0.9300
C4—C8	1.4890 (19)	C13—C14	1.376 (3)
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—H14	0.9300
O2—S1—O1	119.94 (9)	H7A—C7—H7B	109.5
O2—S1—N	105.88 (7)	C1—C7—H7C	109.5
O1—S1—N	107.05 (7)	H7A—C7—H7C	109.5
O2—S1—C9	110.02 (8)	H7B—C7—H7C	109.5
O1—S1—C9	109.26 (8)	C4—C8—H8A	109.5
N—S1—C9	103.33 (7)	C4—C8—H8B	109.5
C4—N—C1	109.39 (11)	H8A—C8—H8B	109.5
C4—N—S1	123.39 (9)	C4—C8—H8C	109.5
C1—N—S1	127.22 (10)	H8A—C8—H8C	109.5
C2—C1—N	107.03 (11)	H8B—C8—H8C	109.5
C2—C1—C7	128.14 (13)	C10—C9—C14	121.40 (16)
N—C1—C7	124.83 (14)	C10—C9—S1	119.29 (14)
C1—C2—C3	108.37 (12)	C14—C9—S1	119.29 (12)
C1—C2—C6	126.27 (13)	C9—C10—C11	118.31 (18)
C3—C2—C6	125.35 (14)	C9—C10—H10	120.8
C4—C3—C2	108.18 (12)	C11—C10—H10	120.8
C4—C3—C5	123.06 (13)	C12—C11—C10	120.27 (18)
C2—C3—C5	128.76 (13)	C12—C11—H11	119.9
C3—C4—N	107.02 (11)	C10—C11—H11	119.9
C3—C4—C8	129.31 (14)	C11—C12—C13	121.2 (2)
N—C4—C8	123.67 (13)	C11—C12—H12	119.4
O3—C5—C3	125.90 (15)	C13—C12—H12	119.4
O3—C5—H5	117.1	C12—C13—C14	119.66 (19)
C3—C5—H5	117.1	C12—C13—H13	120.2
O4—C6—C2	126.33 (18)	C14—C13—H13	120.2
O4—C6—H6	116.8	C13—C14—C9	119.18 (16)
C2—C6—H6	116.8	C13—C14—H14	120.4
C1—C7—H7A	109.5	C9—C14—H14	120.4
C1—C7—H7B	109.5
O2—S1—N—C4	172.55 (12)	C1—N—C4—C3	0.29 (16)
O1—S1—N—C4	43.51 (14)	S1—N—C4—C3	−179.53 (10)
C9—S1—N—C4	−71.78 (13)	C1—N—C4—C8	179.88 (15)
O2—S1—N—C1	−7.23 (15)	S1—N—C4—C8	0.1 (2)
O1—S1—N—C1	−136.28 (13)	C4—C3—C5—O3	−178.68 (17)
C9—S1—N—C1	108.43 (13)	C2—C3—C5—O3	2.1 (3)
C4—N—C1—C2	−1.03 (16)	C1—C2—C6—O4	5.9 (3)
S1—N—C1—C2	178.78 (10)	C3—C2—C6—O4	−173.12 (19)
C4—N—C1—C7	178.16 (15)	O2—S1—C9—C10	−122.33 (14)
S1—N—C1—C7	−2.0 (2)	O1—S1—C9—C10	11.30 (15)
N—C1—C2—C3	1.33 (16)	N—S1—C9—C10	125.00 (13)
C7—C1—C2—C3	−177.83 (16)	O2—S1—C9—C14	55.92 (14)
N—C1—C2—C6	−177.86 (14)	O1—S1—C9—C14	−170.46 (12)
C7—C1—C2—C6	3.0 (3)	N—S1—C9—C14	−56.75 (13)
C1—C2—C3—C4	−1.18 (16)	C14—C9—C10—C11	0.7 (3)
C6—C2—C3—C4	178.02 (14)	S1—C9—C10—C11	178.93 (14)
C1—C2—C3—C5	178.14 (14)	C9—C10—C11—C12	0.3 (3)
C6—C2—C3—C5	−2.7 (2)	C10—C11—C12—C13	−0.4 (3)
C2—C3—C4—N	0.53 (15)	C11—C12—C13—C14	−0.5 (3)
C5—C3—C4—N	−178.84 (13)	C12—C13—C14—C9	1.4 (3)
C2—C3—C4—C8	−179.04 (17)	C10—C9—C14—C13	−1.6 (2)
C5—C3—C4—C8	1.6 (3)	S1—C9—C14—C13	−179.77 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3	0.93	2.46	3.077 (2)	124
C7—H7A···O4	0.96	2.33	3.021 (3)	128
C11—H11···O4i	0.93	2.53	3.456 (2)	174
C13—H13···O2i	0.93	2.52	3.304 (2)	143
C14—H14···O3ii	0.93	2.57	3.383 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O3	0.93	2.46	3.077 (2)	124
C7—H7A⋯O4	0.96	2.33	3.021 (3)	128
C11—H11⋯O4i	0.93	2.53	3.456 (2)	174
C13—H13⋯O2	0.93	2.52	3.304 (2)	143
C14—H14⋯O3ii	0.93	2.57	3.383 (2)	146

Symmetry codes: (i) ; (ii) .