4-Amino-N-(4,6-dimethyl-pyrimidin-2-yl)benzene-sulfonamide-benzoic acid (1/1).

The constituents of the title co-crystal, C(12)H(14)N(4)O(2)S·C(7)H(6)O(2), are connected by an eight-membered hetero-synthon {⋯NCNH⋯OCOH}, whereby the carb-oxy-lic acid forms donor and acceptor hydrogen bonds with a pyrimidine N atom and the adjacent amine, respectively. The dimeric aggregates thus formed are arranged in rows with their terminal NH(2) groups forming N-H⋯O hydrogen bonds with neighbouring aggregates to form a two-dimensional array in the ac plane with an overall T-shaped topology. Layers inter-digitate along the b axis being connected by C-H⋯O, C-H⋯π and π-π [centroid-centroid distance = 3.6316 (19) Å] inter-actions.

Related literature

For related studies on co-crystal formation, see: Broker & Tiekink (2007 ▶); Ellis et al. (2009 ▶); Arman et al. (2010 ▶). For related structures of carb­oxy­lic acids with 4-amino-N-(4,6-dimethyl­pyrimidin-2-yl)benzene-1-sulfonamide, see: Caira (1991 ▶, 1992 ▶).

Experimental

Crystal data

C12H14N4O2S·C7H6O2

M = 400.45

Orthorhombic,

a = 15.203 (6) Å

b = 14.006 (5) Å

c = 18.015 (7) Å

V = 3836 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.20 mm−1

T = 98 K

0.35 × 0.23 × 0.10 mm

Data collection

Rigaku AFC12/SATURN724 diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.828, T max = 1

30274 measured reflections

4404 independent reflections

4137 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.159

S = 1.17

4404 reflections

267 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.55 e Å−3

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034094/hg2707sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034094/hg2707Isup2.hkl

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

C12H14N4O2S·C7H6O2	F(000) = 1680
Mr = 400.45	Dx = 1.387 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 16577 reflections
a = 15.203 (6) Å	θ = 2.3–40.5°
b = 14.006 (5) Å	µ = 0.20 mm−1
c = 18.015 (7) Å	T = 98 K
V = 3836 (2) Å3	Block, colourless
Z = 8	0.35 × 0.23 × 0.10 mm

Rigaku AFC12K/SATURN724 diffractometer	4404 independent reflections
Radiation source: fine-focus sealed tube	4137 reflections with I > 2σ(I)
graphite	Rint = 0.073
ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −19→19
Tmin = 0.828, Tmax = 1	k = −16→18
30274 measured reflections	l = −23→23

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ2(Fo2) + (0.0647P)2 + 3.1388P] where P = (Fo2 + 2Fc2)/3
4404 reflections	(Δ/σ)max = 0.001
267 parameters	Δρmax = 0.41 e Å−3
5 restraints	Δρmin = −0.55 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.54508 (4)	0.60684 (4)	0.73129 (3)	0.02568 (16)
O1	0.60107 (11)	0.68686 (12)	0.74705 (9)	0.0323 (4)
O2	0.45840 (11)	0.60392 (12)	0.76309 (9)	0.0310 (4)
O3	0.35026 (10)	0.58510 (12)	0.59738 (9)	0.0304 (4)
O4	0.38399 (11)	0.61521 (13)	0.47864 (9)	0.0334 (4)
H4O	0.4377 (9)	0.615 (2)	0.4912 (18)	0.050*
N1	0.72042 (15)	0.23929 (16)	0.79698 (14)	0.0402 (5)
H1N	0.7731 (10)	0.2262 (19)	0.7781 (16)	0.048*
H2N	0.6859 (14)	0.1909 (14)	0.8089 (16)	0.048*
N2	0.52506 (13)	0.60582 (14)	0.64115 (10)	0.0277 (4)
H3N	0.4698 (9)	0.5961 (19)	0.6277 (15)	0.033*
N3	0.67129 (12)	0.61923 (13)	0.60236 (10)	0.0258 (4)
N4	0.55167 (12)	0.62139 (13)	0.51621 (10)	0.0249 (4)
C1	0.68116 (15)	0.32487 (17)	0.78271 (12)	0.0296 (5)
C2	0.72999 (15)	0.40339 (17)	0.75643 (12)	0.0289 (5)
H2	0.7915	0.3965	0.7487	0.035*
C3	0.69052 (15)	0.49023 (17)	0.74168 (12)	0.0279 (5)
H3	0.7246	0.5424	0.7241	0.033*
C4	0.59970 (14)	0.50071 (16)	0.75289 (12)	0.0254 (4)
C5	0.55028 (15)	0.42415 (17)	0.78067 (12)	0.0292 (5)
H5	0.4889	0.4315	0.7889	0.035*
C6	0.59063 (16)	0.33828 (17)	0.79608 (13)	0.0317 (5)
H6	0.5569	0.2873	0.8160	0.038*
C7	0.58666 (14)	0.61564 (15)	0.58457 (12)	0.0241 (4)
C8	0.72783 (15)	0.63113 (16)	0.54554 (13)	0.0277 (5)
C9	0.69815 (16)	0.63989 (17)	0.47292 (13)	0.0307 (5)
H9	0.7385	0.6494	0.4333	0.037*
C10	0.60877 (15)	0.63456 (16)	0.45948 (12)	0.0276 (5)
C11	0.82379 (15)	0.63460 (18)	0.56559 (14)	0.0342 (5)
H11A	0.8301	0.6532	0.6178	0.051*
H11B	0.8538	0.6814	0.5340	0.051*
H11C	0.8501	0.5715	0.5581	0.051*
C12	0.57027 (17)	0.64250 (19)	0.38306 (13)	0.0358 (5)
H12A	0.5063	0.6351	0.3858	0.054*
H12B	0.5949	0.5924	0.3513	0.054*
H12C	0.5845	0.7052	0.3621	0.054*
C13	0.23390 (14)	0.60650 (15)	0.51020 (12)	0.0253 (4)
C14	0.21086 (15)	0.63324 (16)	0.43783 (12)	0.0268 (4)
H14	0.2553	0.6452	0.4019	0.032*
C15	0.12273 (15)	0.64217 (17)	0.41883 (13)	0.0300 (5)
H15	0.1069	0.6609	0.3700	0.036*
C16	0.05768 (16)	0.62377 (17)	0.47104 (14)	0.0320 (5)
H16	−0.0025	0.6294	0.4576	0.038*
C17	0.08033 (16)	0.59699 (18)	0.54334 (14)	0.0329 (5)
H17	0.0358	0.5848	0.5791	0.039*
C18	0.16840 (16)	0.58838 (17)	0.56251 (13)	0.0301 (5)
H18	0.1841	0.5700	0.6115	0.036*
C19	0.32779 (15)	0.60083 (15)	0.53280 (12)	0.0262 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0240 (3)	0.0291 (3)	0.0240 (3)	0.0018 (2)	−0.00015 (18)	−0.00016 (19)
O1	0.0319 (9)	0.0304 (8)	0.0346 (8)	−0.0011 (7)	−0.0027 (7)	−0.0038 (7)
O2	0.0234 (8)	0.0397 (10)	0.0299 (8)	0.0061 (7)	0.0035 (6)	0.0030 (7)
O3	0.0270 (8)	0.0375 (9)	0.0268 (8)	−0.0004 (7)	−0.0025 (6)	0.0013 (7)
O4	0.0222 (8)	0.0476 (10)	0.0303 (8)	0.0011 (7)	−0.0003 (6)	0.0051 (7)
N1	0.0340 (11)	0.0322 (11)	0.0544 (13)	0.0047 (9)	0.0073 (10)	0.0061 (10)
N2	0.0212 (9)	0.0359 (10)	0.0259 (9)	−0.0016 (8)	−0.0031 (7)	0.0042 (7)
N3	0.0224 (9)	0.0256 (9)	0.0294 (9)	−0.0004 (7)	0.0004 (7)	0.0013 (7)
N4	0.0263 (9)	0.0235 (9)	0.0249 (9)	−0.0001 (7)	0.0007 (7)	0.0027 (7)
C1	0.0294 (11)	0.0307 (11)	0.0288 (10)	0.0018 (9)	−0.0012 (9)	−0.0004 (9)
C2	0.0226 (10)	0.0366 (12)	0.0275 (10)	0.0012 (9)	−0.0010 (8)	0.0002 (9)
C3	0.0240 (10)	0.0329 (11)	0.0266 (10)	−0.0035 (9)	−0.0011 (8)	0.0022 (9)
C4	0.0263 (11)	0.0276 (10)	0.0225 (9)	0.0005 (9)	−0.0015 (8)	−0.0013 (8)
C5	0.0245 (11)	0.0336 (12)	0.0295 (10)	−0.0020 (9)	0.0017 (8)	−0.0014 (9)
C6	0.0284 (11)	0.0303 (12)	0.0363 (12)	−0.0040 (9)	0.0020 (9)	0.0014 (9)
C7	0.0232 (10)	0.0223 (10)	0.0269 (10)	−0.0009 (8)	−0.0009 (8)	0.0016 (8)
C8	0.0244 (10)	0.0233 (10)	0.0354 (11)	−0.0019 (9)	0.0027 (9)	−0.0003 (9)
C9	0.0298 (11)	0.0310 (11)	0.0311 (11)	−0.0032 (9)	0.0070 (9)	0.0021 (9)
C10	0.0302 (11)	0.0241 (10)	0.0285 (10)	0.0000 (9)	0.0015 (8)	0.0006 (8)
C11	0.0239 (11)	0.0374 (13)	0.0413 (13)	−0.0013 (10)	0.0009 (9)	0.0018 (10)
C12	0.0367 (12)	0.0425 (14)	0.0280 (11)	−0.0014 (11)	0.0012 (10)	0.0046 (10)
C13	0.0251 (10)	0.0227 (10)	0.0281 (10)	0.0014 (8)	−0.0019 (8)	−0.0029 (8)
C14	0.0273 (11)	0.0262 (10)	0.0270 (10)	−0.0008 (9)	0.0000 (8)	−0.0008 (8)
C15	0.0298 (11)	0.0294 (11)	0.0308 (11)	−0.0012 (9)	−0.0075 (9)	−0.0019 (9)
C16	0.0260 (11)	0.0348 (12)	0.0353 (12)	0.0010 (9)	−0.0030 (9)	−0.0028 (10)
C17	0.0253 (11)	0.0388 (13)	0.0346 (12)	−0.0002 (10)	0.0016 (9)	0.0009 (10)
C18	0.0291 (11)	0.0331 (12)	0.0281 (11)	−0.0007 (9)	−0.0012 (9)	0.0008 (9)
C19	0.0264 (11)	0.0242 (10)	0.0280 (10)	0.0002 (8)	−0.0015 (8)	−0.0006 (8)

S1—O1	1.4358 (18)	C6—H6	0.9500
S1—O2	1.4375 (17)	C8—C9	1.389 (3)
S1—N2	1.652 (2)	C8—C11	1.504 (3)
S1—C4	1.747 (2)	C9—C10	1.382 (3)
O3—C19	1.232 (3)	C9—H9	0.9500
O4—C19	1.313 (3)	C10—C12	1.500 (3)
O4—H4O	0.848 (10)	C11—H11A	0.9800
N1—C1	1.364 (3)	C11—H11B	0.9800
N1—H1N	0.889 (9)	C11—H11C	0.9800
N1—H2N	0.88 (2)	C12—H12A	0.9800
N2—C7	1.391 (3)	C12—H12B	0.9800
N2—H3N	0.886 (10)	C12—H12C	0.9800
N3—C7	1.327 (3)	C13—C18	1.394 (3)
N3—C8	1.347 (3)	C13—C14	1.401 (3)
N4—C7	1.344 (3)	C13—C19	1.486 (3)
N4—C10	1.353 (3)	C14—C15	1.388 (3)
C1—C2	1.409 (3)	C14—H14	0.9500
C1—C6	1.410 (3)	C15—C16	1.389 (3)
C2—C3	1.382 (3)	C15—H15	0.9500
C2—H2	0.9500	C16—C17	1.398 (3)
C3—C4	1.403 (3)	C16—H16	0.9500
C3—H3	0.9500	C17—C18	1.388 (3)
C4—C5	1.402 (3)	C17—H17	0.9500
C5—C6	1.378 (3)	C18—H18	0.9500
C5—H5	0.9500
O1—S1—O2	119.14 (10)	C10—C9—C8	118.6 (2)
O1—S1—N2	108.07 (10)	C10—C9—H9	120.7
O2—S1—N2	102.86 (10)	C8—C9—H9	120.7
O1—S1—C4	109.78 (11)	N4—C10—C9	120.4 (2)
O2—S1—C4	108.84 (10)	N4—C10—C12	116.9 (2)
N2—S1—C4	107.40 (10)	C9—C10—C12	122.7 (2)
C19—O4—H4O	115 (2)	C8—C11—H11A	109.5
C1—N1—H1N	120.3 (18)	C8—C11—H11B	109.5
C1—N1—H2N	117.5 (18)	H11A—C11—H11B	109.5
H1N—N1—H2N	117.9 (14)	C8—C11—H11C	109.5
C7—N2—S1	126.54 (16)	H11A—C11—H11C	109.5
C7—N2—H3N	117.0 (18)	H11B—C11—H11C	109.5
S1—N2—H3N	116.4 (18)	C10—C12—H12A	109.5
C7—N3—C8	116.1 (2)	C10—C12—H12B	109.5
C7—N4—C10	116.50 (19)	H12A—C12—H12B	109.5
N1—C1—C2	121.3 (2)	C10—C12—H12C	109.5
N1—C1—C6	120.8 (2)	H12A—C12—H12C	109.5
C2—C1—C6	117.9 (2)	H12B—C12—H12C	109.5
C3—C2—C1	121.5 (2)	C18—C13—C14	119.9 (2)
C3—C2—H2	119.2	C18—C13—C19	119.4 (2)
C1—C2—H2	119.2	C14—C13—C19	120.6 (2)
C2—C3—C4	119.4 (2)	C15—C14—C13	119.7 (2)
C2—C3—H3	120.3	C15—C14—H14	120.2
C4—C3—H3	120.3	C13—C14—H14	120.2
C5—C4—C3	119.9 (2)	C14—C15—C16	120.2 (2)
C5—C4—S1	118.40 (17)	C14—C15—H15	119.9
C3—C4—S1	121.66 (17)	C16—C15—H15	119.9
C6—C5—C4	120.1 (2)	C15—C16—C17	120.3 (2)
C6—C5—H5	120.0	C15—C16—H16	119.8
C4—C5—H5	120.0	C17—C16—H16	119.8
C5—C6—C1	121.1 (2)	C18—C17—C16	119.5 (2)
C5—C6—H6	119.5	C18—C17—H17	120.2
C1—C6—H6	119.5	C16—C17—H17	120.2
N3—C7—N4	127.1 (2)	C17—C18—C13	120.3 (2)
N3—C7—N2	118.66 (19)	C17—C18—H18	119.8
N4—C7—N2	114.27 (19)	C13—C18—H18	119.8
N3—C8—C9	121.3 (2)	O3—C19—O4	123.3 (2)
N3—C8—C11	116.1 (2)	O3—C19—C13	122.3 (2)
C9—C8—C11	122.6 (2)	O4—C19—C13	114.41 (19)
O1—S1—N2—C7	47.5 (2)	S1—N2—C7—N3	5.5 (3)
O2—S1—N2—C7	174.35 (18)	S1—N2—C7—N4	−173.94 (16)
C4—S1—N2—C7	−70.9 (2)	C7—N3—C8—C9	0.6 (3)
N1—C1—C2—C3	179.8 (2)	C7—N3—C8—C11	−179.64 (19)
C6—C1—C2—C3	−2.1 (3)	N3—C8—C9—C10	−1.1 (3)
C1—C2—C3—C4	−0.2 (3)	C11—C8—C9—C10	179.1 (2)
C2—C3—C4—C5	1.7 (3)	C7—N4—C10—C9	1.1 (3)
C2—C3—C4—S1	−177.03 (17)	C7—N4—C10—C12	−179.1 (2)
O1—S1—C4—C5	145.66 (18)	C8—C9—C10—N4	0.2 (3)
O2—S1—C4—C5	13.6 (2)	C8—C9—C10—C12	−179.6 (2)
N2—S1—C4—C5	−97.07 (19)	C18—C13—C14—C15	0.5 (3)
O1—S1—C4—C3	−35.6 (2)	C19—C13—C14—C15	−177.2 (2)
O2—S1—C4—C3	−167.67 (17)	C13—C14—C15—C16	−0.6 (3)
N2—S1—C4—C3	81.6 (2)	C14—C15—C16—C17	0.6 (4)
C3—C4—C5—C6	−0.8 (3)	C15—C16—C17—C18	−0.4 (4)
S1—C4—C5—C6	177.91 (17)	C16—C17—C18—C13	0.2 (4)
C4—C5—C6—C1	−1.5 (4)	C14—C13—C18—C17	−0.2 (3)
N1—C1—C6—C5	−179.0 (2)	C19—C13—C18—C17	177.4 (2)
C2—C1—C6—C5	3.0 (3)	C18—C13—C19—O3	−3.6 (3)
C8—N3—C7—N4	0.9 (3)	C14—C13—C19—O3	174.0 (2)
C8—N3—C7—N2	−178.43 (19)	C18—C13—C19—O4	177.3 (2)
C10—N4—C7—N3	−1.7 (3)	C14—C13—C19—O4	−5.1 (3)
C10—N4—C7—N2	177.64 (19)

Cg1 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4o···N4	0.847 (16)	1.793 (16)	2.639 (3)	177 (3)
N2—H3n···O3	0.885 (15)	1.904 (16)	2.787 (3)	176 (3)
N1—H1n···O1i	0.889 (18)	2.068 (18)	2.952 (3)	173 (3)
N1—H2n···O3ii	0.88 (2)	2.31 (3)	3.073 (3)	144 (2)
C12—H12c···O1iii	0.98	2.58	3.455 (3)	149
C11—H11c···Cg1iv	0.98	2.76	3.672 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4o⋯N4	0.85 (2)	1.79 (2)	2.639 (3)	177 (3)
N2—H3n⋯O3	0.89 (2)	1.90 (2)	2.787 (3)	176 (3)
N1—H1n⋯O1i	0.89 (2)	2.07 (2)	2.952 (3)	173 (3)
N1—H2n⋯O3ii	0.88 (2)	2.31 (3)	3.073 (3)	144 (2)
C12—H12c⋯O1iii	0.98	2.58	3.455 (3)	149
C11—H11c⋯Cg1iv	0.98	2.76	3.672 (3)	155

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