4-Amino-N-(6-chloro-5-methoxy-pyrimidin-4-yl)benzene-sulfonamide.

In the title compound, C(11)H(11)ClN(4)O(3)S, the S atom is bonded in a distorted tetra-hedral geometry, by two O atoms, a C atom of the benzene ring and an amino N atom. The essentially planar pyrimidine ring [maximum deviation = 0.020 (1) Å] forms a dihedral angle of 87.57 (5)° with the benzene ring. In the crystal structure, pairs of mol-ecules are linked by inter-molecular N-H⋯O hydrogen bonds to generate centrosymmetric R(2) (2)(8) ring motifs. In addition, mol-ecules are linked into a three-dimensional extended network by inter-molecular N-H⋯N, N-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For general background to and applications of the title compound, see: Amir et al. (2007 ▶); Calabresi et al. (1975 ▶); El-Hashash et al. (1993 ▶); Nagaraja et al. (2003 ▶); Townsend & Drach (2002 ▶). For a related structure, see: Chohan et al. (2008 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H11ClN4O3S

M = 314.75

Monoclinic,

a = 12.8792 (6) Å

b = 13.3557 (6) Å

c = 8.0867 (4) Å

β = 102.396 (1)°

V = 1358.57 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.45 mm−1

T = 100 K

0.44 × 0.33 × 0.12 mm

Data collection

Bruker SMART APEX DUO area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.829, T max = 0.950

20122 measured reflections

4863 independent reflections

4292 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.089

S = 1.04

4863 reflections

225 parameters

All H-atom parameters refined

Δρmax = 0.53 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810001121/lh2975sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001121/lh2975Isup2.hkl

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

C11H11ClN4O3S	F(000) = 648
Mr = 314.75	Dx = 1.539 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9451 reflections
a = 12.8792 (6) Å	θ = 3.1–35.0°
b = 13.3557 (6) Å	µ = 0.45 mm−1
c = 8.0867 (4) Å	T = 100 K
β = 102.396 (1)°	Plate, colourless
V = 1358.57 (11) Å3	0.44 × 0.33 × 0.12 mm
Z = 4

Bruker SMART APEX DUO area-detector diffractometer	4863 independent reflections
Radiation source: fine-focus sealed tube	4292 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 32.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −19→18
Tmin = 0.829, Tmax = 0.950	k = −20→20
20122 measured reflections	l = −11→12

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) = 0.089	All H-atom parameters refined
S = 1.04	w = 1/[σ2(Fo2) + (0.0475P)2 + 0.4528P] where P = (Fo2 + 2Fc2)/3
4863 reflections	(Δ/σ)max < 0.001
225 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl1	0.32221 (2)	0.130087 (19)	0.89383 (4)	0.02300 (7)
S1	0.150384 (18)	0.591224 (17)	0.98106 (3)	0.01312 (6)
O1	0.19845 (6)	0.64388 (6)	0.86316 (9)	0.01714 (14)
O2	0.03978 (6)	0.60773 (6)	0.97922 (10)	0.01793 (14)
O3	0.15020 (6)	0.26617 (6)	0.97198 (9)	0.01711 (14)
N1	0.40417 (8)	0.62924 (7)	1.67597 (11)	0.02030 (18)
N2	0.15327 (7)	0.46898 (6)	0.94120 (11)	0.01577 (15)
N3	0.32756 (7)	0.46232 (7)	0.89578 (12)	0.01792 (16)
N4	0.40819 (7)	0.30443 (7)	0.86117 (13)	0.01997 (17)
C1	0.32974 (8)	0.63720 (7)	1.21150 (12)	0.01551 (17)
C2	0.38928 (8)	0.64543 (8)	1.37493 (13)	0.01691 (17)
C3	0.34401 (8)	0.62413 (7)	1.51452 (12)	0.01546 (17)
C4	0.23638 (8)	0.59518 (8)	1.48550 (13)	0.01756 (18)
C5	0.17708 (8)	0.58676 (8)	1.32262 (13)	0.01685 (18)
C6	0.22376 (7)	0.60750 (7)	1.18497 (12)	0.01355 (16)
C7	0.24116 (7)	0.41496 (7)	0.92115 (12)	0.01407 (16)
C8	0.23504 (7)	0.30973 (7)	0.92579 (12)	0.01413 (16)
C9	0.32214 (8)	0.25928 (7)	0.89322 (12)	0.01631 (17)
C10	0.40614 (8)	0.40413 (8)	0.86664 (15)	0.0207 (2)
C11	0.07329 (9)	0.21978 (10)	0.83669 (16)	0.0253 (2)
H1A	0.3591 (13)	0.6546 (12)	1.120 (2)	0.025 (4)*
H2A	0.4615 (13)	0.6672 (13)	1.393 (2)	0.027 (4)*
H4A	0.2078 (13)	0.5806 (12)	1.581 (2)	0.027 (4)*
H5A	0.1038 (13)	0.5624 (12)	1.303 (2)	0.026 (4)*
H10A	0.4693 (14)	0.4379 (13)	0.847 (2)	0.030 (4)*
H11A	0.0146 (14)	0.2042 (14)	0.883 (2)	0.035 (4)*
H11B	0.0532 (14)	0.2688 (14)	0.743 (2)	0.038 (5)*
H11C	0.0991 (15)	0.1654 (16)	0.795 (2)	0.043 (5)*
H1N1	0.4646 (14)	0.6617 (14)	1.695 (2)	0.033 (4)*
H2N1	0.3696 (15)	0.6271 (14)	1.759 (2)	0.034 (5)*
H1N2	0.1012 (14)	0.4342 (13)	0.968 (2)	0.030 (4)*

	U11	U22	U33	U12	U13	U23
Cl1	0.02251 (13)	0.01320 (11)	0.03324 (15)	0.00115 (8)	0.00591 (10)	−0.00126 (9)
S1	0.01184 (10)	0.01368 (11)	0.01457 (11)	0.00149 (7)	0.00442 (8)	0.00027 (7)
O1	0.0191 (3)	0.0179 (3)	0.0156 (3)	0.0009 (3)	0.0064 (3)	0.0026 (2)
O2	0.0121 (3)	0.0195 (3)	0.0228 (3)	0.0032 (2)	0.0050 (3)	0.0005 (3)
O3	0.0161 (3)	0.0188 (3)	0.0177 (3)	−0.0056 (3)	0.0064 (3)	−0.0027 (3)
N1	0.0241 (4)	0.0228 (4)	0.0140 (4)	−0.0020 (3)	0.0041 (3)	−0.0002 (3)
N2	0.0129 (3)	0.0139 (3)	0.0220 (4)	−0.0005 (3)	0.0071 (3)	−0.0028 (3)
N3	0.0143 (4)	0.0154 (4)	0.0260 (4)	0.0000 (3)	0.0085 (3)	−0.0005 (3)
N4	0.0161 (4)	0.0172 (4)	0.0285 (4)	0.0019 (3)	0.0091 (3)	0.0003 (3)
C1	0.0155 (4)	0.0164 (4)	0.0160 (4)	−0.0008 (3)	0.0063 (3)	0.0003 (3)
C2	0.0159 (4)	0.0189 (4)	0.0167 (4)	−0.0015 (3)	0.0053 (3)	0.0000 (3)
C3	0.0191 (4)	0.0130 (4)	0.0148 (4)	0.0011 (3)	0.0049 (3)	−0.0002 (3)
C4	0.0202 (4)	0.0185 (4)	0.0161 (4)	−0.0004 (3)	0.0087 (3)	0.0009 (3)
C5	0.0157 (4)	0.0188 (4)	0.0178 (4)	−0.0007 (3)	0.0076 (3)	0.0008 (3)
C6	0.0135 (4)	0.0136 (4)	0.0145 (4)	0.0006 (3)	0.0049 (3)	0.0000 (3)
C7	0.0123 (4)	0.0149 (4)	0.0154 (4)	0.0003 (3)	0.0041 (3)	−0.0017 (3)
C8	0.0137 (4)	0.0148 (4)	0.0144 (4)	−0.0013 (3)	0.0041 (3)	−0.0010 (3)
C9	0.0167 (4)	0.0135 (4)	0.0189 (4)	0.0011 (3)	0.0042 (3)	−0.0011 (3)
C10	0.0153 (4)	0.0180 (4)	0.0313 (5)	0.0004 (3)	0.0103 (4)	−0.0002 (4)
C11	0.0196 (5)	0.0299 (6)	0.0268 (5)	−0.0086 (4)	0.0058 (4)	−0.0109 (4)

Cl1—C9	1.7255 (10)	C1—C2	1.3826 (14)
S1—O1	1.4283 (7)	C1—C6	1.3932 (13)
S1—O2	1.4383 (7)	C1—H1A	0.931 (16)
S1—N2	1.6662 (9)	C2—C3	1.4063 (13)
S1—C6	1.7292 (10)	C2—H2A	0.955 (17)
O3—C8	1.3590 (11)	C3—C4	1.4094 (14)
O3—C11	1.4480 (13)	C4—C5	1.3781 (15)
N1—C3	1.3694 (13)	C4—H4A	0.941 (17)
N1—H1N1	0.875 (18)	C5—C6	1.4016 (13)
N1—H2N1	0.879 (19)	C5—H5A	0.979 (16)
N2—C7	1.3809 (12)	C7—C8	1.4085 (14)
N2—H1N2	0.880 (18)	C8—C9	1.3816 (13)
N3—C7	1.3336 (12)	C10—H10A	0.973 (17)
N3—C10	1.3364 (13)	C11—H11A	0.938 (18)
N4—C10	1.3328 (14)	C11—H11B	0.991 (19)
N4—C9	1.3351 (13)	C11—H11C	0.90 (2)
O1—S1—O2	119.20 (5)	C3—C4—H4A	117.7 (10)
O1—S1—N2	108.81 (4)	C4—C5—C6	119.92 (9)
O2—S1—N2	102.20 (4)	C4—C5—H5A	119.9 (10)
O1—S1—C6	110.38 (5)	C6—C5—H5A	120.1 (10)
O2—S1—C6	109.14 (5)	C1—C6—C5	120.47 (9)
N2—S1—C6	106.10 (5)	C1—C6—S1	119.96 (7)
C8—O3—C11	115.81 (8)	C5—C6—S1	119.52 (8)
C3—N1—H1N1	119.3 (12)	N3—C7—N2	120.16 (9)
C3—N1—H2N1	116.6 (12)	N3—C7—C8	122.05 (9)
H1N1—N1—H2N1	117.5 (17)	N2—C7—C8	117.78 (8)
C7—N2—S1	125.98 (7)	O3—C8—C9	125.25 (9)
C7—N2—H1N2	116.1 (11)	O3—C8—C7	119.17 (8)
S1—N2—H1N2	114.8 (11)	C9—C8—C7	115.41 (9)
C7—N3—C10	116.09 (9)	N4—C9—C8	123.96 (9)
C10—N4—C9	114.94 (9)	N4—C9—Cl1	116.89 (7)
C2—C1—C6	119.60 (9)	C8—C9—Cl1	119.15 (8)
C2—C1—H1A	120.2 (10)	N4—C10—N3	127.44 (10)
C6—C1—H1A	120.1 (10)	N4—C10—H10A	115.8 (10)
C1—C2—C3	120.71 (9)	N3—C10—H10A	116.8 (10)
C1—C2—H2A	119.7 (10)	O3—C11—H11A	105.7 (11)
C3—C2—H2A	119.6 (10)	O3—C11—H11B	108.5 (11)
N1—C3—C2	120.53 (9)	H11A—C11—H11B	110.6 (15)
N1—C3—C4	120.49 (9)	O3—C11—H11C	112.6 (12)
C2—C3—C4	118.96 (9)	H11A—C11—H11C	111.6 (17)
C5—C4—C3	120.34 (9)	H11B—C11—H11C	107.8 (16)
C5—C4—H4A	122.0 (10)
O1—S1—N2—C7	49.81 (10)	C10—N3—C7—N2	−175.76 (10)
O2—S1—N2—C7	176.75 (8)	C10—N3—C7—C8	3.19 (15)
C6—S1—N2—C7	−68.95 (9)	S1—N2—C7—N3	−14.89 (14)
C6—C1—C2—C3	0.01 (15)	S1—N2—C7—C8	166.11 (7)
C1—C2—C3—N1	177.89 (10)	C11—O3—C8—C9	−78.05 (13)
C1—C2—C3—C4	−0.66 (15)	C11—O3—C8—C7	106.84 (11)
N1—C3—C4—C5	−177.74 (10)	N3—C7—C8—O3	172.23 (9)
C2—C3—C4—C5	0.80 (15)	N2—C7—C8—O3	−8.80 (13)
C3—C4—C5—C6	−0.30 (15)	N3—C7—C8—C9	−3.36 (14)
C2—C1—C6—C5	0.51 (15)	N2—C7—C8—C9	175.62 (9)
C2—C1—C6—S1	−176.93 (8)	C10—N4—C9—C8	1.60 (15)
C4—C5—C6—C1	−0.37 (15)	C10—N4—C9—Cl1	−178.19 (8)
C4—C5—C6—S1	177.08 (8)	O3—C8—C9—N4	−174.46 (10)
O1—S1—C6—C1	−20.24 (9)	C7—C8—C9—N4	0.82 (14)
O2—S1—C6—C1	−153.06 (8)	O3—C8—C9—Cl1	5.32 (14)
N2—S1—C6—C1	97.49 (8)	C7—C8—C9—Cl1	−179.40 (7)
O1—S1—C6—C5	162.29 (8)	C9—N4—C10—N3	−1.89 (18)
O2—S1—C6—C5	29.47 (9)	C7—N3—C10—N4	−0.47 (18)
N2—S1—C6—C5	−79.98 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···N4i	0.875 (19)	2.616 (18)	3.4230 (14)	153.8 (15)
N1—H2N1···O1ii	0.882 (18)	2.533 (19)	3.3274 (13)	150.2 (15)
N2—H1N2···O2iii	0.880 (18)	2.031 (18)	2.8866 (12)	163.7 (16)
C4—H4A···O1ii	0.944 (16)	2.460 (16)	3.2603 (13)	142.5 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯N4i	0.875 (19)	2.616 (18)	3.4230 (14)	153.8 (15)
N1—H2N1⋯O1ii	0.882 (18)	2.533 (19)	3.3274 (13)	150.2 (15)
N2—H1N2⋯O2iii	0.880 (18)	2.031 (18)	2.8866 (12)	163.7 (16)
C4—H4A⋯O1ii	0.944 (16)	2.460 (16)	3.2603 (13)	142.5 (13)

Symmetry codes: (i) ; (ii) ; (iii) .