N-(2-Hy-droxy-5-nitro-phen-yl)methane-sulfonamide ethanol monosolvate.

In the title compound, C(7)H(8)N(2)O(5)S·C(2)H(6)O, the dihedral angle between the aromatic ring and the nitro group is 8.78 (9)° and the S atom is displaced by 0.226 (3) Å from the plane of the aromatic ring. In the crystal, the ethanol mol-ecule is involved in hydrogen bonding to two separate sulfonamide mol-ecules, as a donor in an O-H⋯O inter-action and as an acceptor in an N-H⋯O inter-action. Weak C-H⋯O hydrogen bonding is also present.

Related literature

The title compound is an inter­mediate in the preparation of derivatives of the aromatase inhibitor nimesulide [systematic name N-(4-nitro-2-phen­oxy­phen­yl)methane­sulfonamide]. For background to the bioactivity and applications of nimesulide, see: Diaz-Cruz et al. (2005 ▶). For the synthesis of other nimesulide derivatives, see: Su et al. (2006 ▶); Wang et al. (2007 ▶). For a related structure, see: Gowda et al. (2007 ▶).

Experimental

Crystal data

C7H8N2O5S·C2H6O

M = 278.28

Monoclinic,

a = 11.709 (3) Å

b = 8.8521 (18) Å

c = 12.439 (3) Å

β = 112.459 (7)°

V = 1191.5 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 113 K

0.20 × 0.18 × 0.16 mm

Data collection

Rigaku Saturn CCD area detector diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.943, T max = 0.954

12473 measured reflections

2840 independent reflections

2091 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.079

S = 0.98

2840 reflections

177 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.36 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017090/fl2343sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017090/fl2343Isup2.hkl

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

C7H8N2O5S·C2H6O	F(000) = 584
Mr = 278.28	Dx = 1.551 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4097 reflections
a = 11.709 (3) Å	θ = 1.8–27.9°
b = 8.8521 (18) Å	µ = 0.30 mm−1
c = 12.439 (3) Å	T = 113 K
β = 112.459 (7)°	Prism, colourless
V = 1191.5 (5) Å3	0.20 × 0.18 × 0.16 mm
Z = 4

Rigaku Saturn CCD area detector diffractometer	2840 independent reflections
Radiation source: rotating anode	2091 reflections with I > 2σ(I)
multilayer	Rint = 0.045
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 1.9°
ω and φ scans	h = −15→15
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −9→11
Tmin = 0.943, Tmax = 0.954	l = −16→16
12473 measured reflections

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ2(Fo2) + (0.0421P)2] where P = (Fo2 + 2Fc2)/3
2840 reflections	(Δ/σ)max = 0.001
177 parameters	Δρmax = 0.33 e Å−3
1 restraint	Δρmin = −0.36 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	0.23077 (3)	0.44845 (4)	0.61896 (3)	0.01396 (10)
O1	0.14081 (9)	0.51062 (11)	0.65857 (8)	0.0200 (2)
O2	0.34570 (9)	0.52619 (10)	0.64474 (8)	0.0187 (2)
O3	0.37065 (9)	0.01532 (12)	0.74369 (9)	0.0186 (2)
H3	0.4002 (16)	−0.069 (2)	0.7674 (14)	0.038 (6)*
O4	−0.18590 (9)	0.18630 (12)	0.56941 (9)	0.0263 (3)
O5	−0.20141 (9)	−0.05693 (11)	0.57761 (9)	0.0240 (3)
N1	0.27051 (11)	0.28099 (13)	0.67419 (10)	0.0160 (3)
N2	−0.13955 (11)	0.05910 (14)	0.59166 (10)	0.0185 (3)
C1	0.16076 (13)	0.42769 (17)	0.46762 (11)	0.0207 (3)
H1A	0.1501	0.5273	0.4306	0.031*
H1B	0.0799	0.3794	0.4472	0.031*
H1C	0.2132	0.3648	0.4404	0.031*
C2	0.19037 (12)	0.16067 (15)	0.67166 (11)	0.0138 (3)
C3	0.06316 (12)	0.17416 (16)	0.63523 (11)	0.0151 (3)
H3A	0.0237	0.2689	0.6104	0.018*
C4	−0.00540 (13)	0.04612 (16)	0.63584 (11)	0.0153 (3)
C5	0.04822 (13)	−0.09282 (16)	0.67288 (11)	0.0169 (3)
H5	−0.0010	−0.1780	0.6732	0.020*
C6	0.17558 (13)	−0.10593 (16)	0.70973 (11)	0.0165 (3)
H6	0.2141	−0.2009	0.7354	0.020*
C7	0.24676 (12)	0.01876 (16)	0.70925 (11)	0.0143 (3)
H1	0.3450 (15)	0.2597 (17)	0.6838 (12)	0.022 (4)*
O6	0.52899 (9)	0.24326 (11)	0.69398 (9)	0.0171 (2)
H6A	0.5557 (16)	0.1858 (19)	0.7445 (13)	0.033 (5)*
C8	0.52156 (14)	0.16205 (16)	0.58969 (12)	0.0210 (3)
H8A	0.4508	0.0912	0.5656	0.025*
H8B	0.5981	0.1029	0.6057	0.025*
C9	0.50525 (15)	0.27419 (19)	0.49432 (12)	0.0307 (4)
H9A	0.4315	0.3355	0.4814	0.046*
H9B	0.4957	0.2203	0.4226	0.046*
H9C	0.5780	0.3400	0.5168	0.046*

	U11	U22	U33	U12	U13	U23
S1	0.01380 (18)	0.01101 (19)	0.01618 (18)	−0.00055 (13)	0.00473 (13)	−0.00005 (13)
O1	0.0206 (5)	0.0166 (5)	0.0246 (6)	0.0028 (4)	0.0106 (4)	−0.0020 (4)
O2	0.0151 (5)	0.0144 (5)	0.0242 (5)	−0.0039 (4)	0.0049 (4)	−0.0002 (4)
O3	0.0137 (5)	0.0142 (6)	0.0261 (6)	0.0028 (4)	0.0056 (4)	0.0053 (4)
O4	0.0184 (6)	0.0224 (6)	0.0383 (6)	0.0036 (5)	0.0111 (5)	0.0001 (5)
O5	0.0188 (6)	0.0236 (6)	0.0297 (6)	−0.0097 (5)	0.0095 (5)	−0.0065 (4)
N1	0.0103 (6)	0.0133 (6)	0.0232 (6)	0.0006 (5)	0.0051 (5)	0.0034 (5)
N2	0.0178 (6)	0.0221 (7)	0.0176 (6)	−0.0025 (5)	0.0092 (5)	−0.0037 (5)
C1	0.0209 (8)	0.0227 (8)	0.0164 (7)	−0.0004 (6)	0.0047 (6)	0.0010 (6)
C2	0.0156 (7)	0.0134 (7)	0.0134 (6)	−0.0015 (5)	0.0065 (5)	−0.0006 (5)
C3	0.0168 (7)	0.0138 (7)	0.0150 (6)	0.0011 (6)	0.0064 (5)	−0.0001 (5)
C4	0.0136 (7)	0.0201 (8)	0.0136 (7)	−0.0023 (6)	0.0068 (5)	−0.0034 (5)
C5	0.0210 (8)	0.0150 (7)	0.0163 (7)	−0.0066 (6)	0.0089 (6)	−0.0023 (5)
C6	0.0191 (7)	0.0133 (7)	0.0170 (7)	0.0011 (6)	0.0070 (6)	0.0019 (6)
C7	0.0145 (7)	0.0161 (8)	0.0127 (7)	0.0005 (6)	0.0055 (5)	−0.0007 (5)
O6	0.0188 (5)	0.0137 (6)	0.0184 (5)	0.0008 (4)	0.0069 (4)	0.0012 (4)
C8	0.0245 (8)	0.0192 (8)	0.0207 (7)	−0.0015 (6)	0.0102 (6)	−0.0032 (6)
C9	0.0349 (10)	0.0359 (10)	0.0249 (8)	0.0045 (8)	0.0155 (7)	0.0059 (7)

S1—O1	1.4323 (10)	C3—C4	1.3906 (19)
S1—O2	1.4344 (10)	C3—H3A	0.9500
S1—N1	1.6254 (12)	C4—C5	1.378 (2)
S1—C1	1.7523 (14)	C5—C6	1.3875 (19)
O3—C7	1.3468 (17)	C5—H5	0.9500
O3—H3	0.830 (18)	C6—C7	1.3845 (19)
O4—N2	1.2345 (15)	C6—H6	0.9500
O5—N2	1.2302 (15)	O6—C8	1.4564 (16)
N1—C2	1.4119 (17)	O6—H6A	0.776 (15)
N1—H1	0.855 (16)	C8—C9	1.502 (2)
N2—C4	1.4571 (18)	C8—H8A	0.9900
C1—H1A	0.9800	C8—H8B	0.9900
C1—H1B	0.9800	C9—H9A	0.9800
C1—H1C	0.9800	C9—H9B	0.9800
C2—C3	1.3865 (19)	C9—H9C	0.9800
C2—C7	1.4130 (19)
O1—S1—O2	119.28 (6)	C5—C4—C3	122.62 (13)
O1—S1—N1	109.54 (6)	C5—C4—N2	118.98 (12)
O2—S1—N1	104.50 (6)	C3—C4—N2	118.37 (12)
O1—S1—C1	107.83 (7)	C4—C5—C6	118.70 (13)
O2—S1—C1	107.72 (7)	C4—C5—H5	120.7
N1—S1—C1	107.42 (7)	C6—C5—H5	120.7
C7—O3—H3	112.7 (12)	C7—C6—C5	120.31 (13)
C2—N1—S1	126.73 (10)	C7—C6—H6	119.8
C2—N1—H1	118.1 (10)	C5—C6—H6	119.8
S1—N1—H1	111.8 (10)	O3—C7—C6	123.89 (13)
O5—N2—O4	123.04 (12)	O3—C7—C2	115.83 (12)
O5—N2—C4	118.62 (12)	C6—C7—C2	120.28 (13)
O4—N2—C4	118.34 (12)	C8—O6—H6A	105.5 (13)
S1—C1—H1A	109.5	O6—C8—C9	108.88 (12)
S1—C1—H1B	109.5	O6—C8—H8A	109.9
H1A—C1—H1B	109.5	C9—C8—H8A	109.9
S1—C1—H1C	109.5	O6—C8—H8B	109.9
H1A—C1—H1C	109.5	C9—C8—H8B	109.9
H1B—C1—H1C	109.5	H8A—C8—H8B	108.3
C3—C2—N1	124.34 (12)	C8—C9—H9A	109.5
C3—C2—C7	119.51 (12)	C8—C9—H9B	109.5
N1—C2—C7	116.14 (12)	H9A—C9—H9B	109.5
C2—C3—C4	118.57 (13)	C8—C9—H9C	109.5
C2—C3—H3A	120.7	H9A—C9—H9C	109.5
C4—C3—H3A	120.7	H9B—C9—H9C	109.5
O1—S1—N1—C2	51.29 (13)	O5—N2—C4—C3	170.54 (12)
O2—S1—N1—C2	−179.82 (11)	O4—N2—C4—C3	−9.04 (18)
C1—S1—N1—C2	−65.57 (13)	C3—C4—C5—C6	−0.8 (2)
S1—N1—C2—C3	−9.6 (2)	N2—C4—C5—C6	177.01 (11)
S1—N1—C2—C7	170.35 (10)	C4—C5—C6—C7	0.13 (19)
N1—C2—C3—C4	179.32 (12)	C5—C6—C7—O3	179.95 (12)
C7—C2—C3—C4	−0.63 (19)	C5—C6—C7—C2	0.25 (19)
C2—C3—C4—C5	1.0 (2)	C3—C2—C7—O3	−179.72 (11)
C2—C3—C4—N2	−176.78 (11)	N1—C2—C7—O3	0.33 (17)
O5—N2—C4—C5	−7.36 (18)	C3—C2—C7—C6	0.0 (2)
O4—N2—C4—C5	173.06 (12)	N1—C2—C7—C6	−179.95 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O6i	0.830 (18)	1.835 (19)	2.6619 (15)	173.6 (17)
N1—H1···O6	0.855 (16)	2.114 (16)	2.9601 (17)	170.2 (14)
O6—H6A···O2i	0.78 (2)	2.00 (2)	2.7605 (14)	166 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O6i	0.830 (18)	1.835 (19)	2.6619 (15)	173.6 (17)
N1—H1⋯O6	0.855 (16)	2.114 (16)	2.9601 (17)	170.2 (14)
O6—H6A⋯O2i	0.78 (2)	2.00 (2)	2.7605 (14)	166 (2)

Symmetry code: (i) .