4-Amino-N-(4,6-dimethyl­pyrimidin-2-yl)benzene­sulfonamide–2-nitro­benzoic acid (1/1)

Smith, G.; Wermuth, U.D.

doi:10.1107/S1600536813000779

organic compounds

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Volume 69| Part 2| February 2013| Page o234

doi:10.1107/S1600536813000779

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4-Amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide–2-nitrobenzoic acid (1/1)

Graham Smith ^a ^* and Urs D. Wermuth ^a

^aScience and Engineering Faculty, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia
^*Correspondence e-mail: g.smith@qut.edu.au

(Received 15 December 2012; accepted 8 January 2013; online 12 January 2013)

In the asymmetric unit of the title co-crystal, C₁₂H₁₄N₄O₂S·C₇H₅NO₄, the sulfamethazine and 2-nitrobenzoic acid molecules form a heterodimer through intermolecular amide–carboxylic acid N—H⋯O and carboxylic acid–pyrimidine O—H⋯N hydrogen-bond pairs, giving a cyclic motif [graph set R₂²(8)]. The dihedral angle between the two aromatic ring systems in the sulfamethazine molecule is 88.96 (18)° and the nitro group of the acid is 50% rotationally disordered. Secondary aniline N—H⋯O_sulfone hydrogen-bonding associations give a two-dimensional structure lying parallel to the ab plane.

Related literature

For background to sulfamethazole as a model for co-crystal formation, see: Caira (2007 ); Ghosh et al. (2011 ). For structures of 1:1 adducts of sulfamethazine with nitrobenzoic acid analogues, see: Lynch et al. (2000 ); Smith & Wermuth (2012 ). For graph-set analysis, see: Etter et al. (1990 ).

Experimental

Crystal data

C₁₂H₁₄N₄O₂S·C₇H₅NO₄
M_r = 445.46
Orthorhombic, P n a 2₁
a = 14.2945 (4) Å
b = 8.0115 (3) Å
c = 19.0962 (5) Å
V = 2186.91 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 200 K
0.30 × 0.21 × 0.12 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.964, T_max = 0.980
5541 measured reflections
2777 independent reflections
2587 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.099
S = 1.04
2777 reflections
286 parameters
29 restraints
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 565 Friedel pairs
Flack parameter: 0.08 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O12—H12⋯N1A	0.90	1.77	2.671 (4)	180
N2A—H2A⋯O11	0.90	2.01	2.862 (4)	158
N41A—H41A⋯O11Aⁱ	0.92	2.18	2.990 (3)	147
N41A—H42A⋯O12Aⁱⁱ	0.83	2.24	2.973 (3)	146
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (ii) x, y-1, z.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ) within WinGX (Farrugia, 2012 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813000779/gg2106sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813000779/gg2106Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813000779/gg2106Isup3.cml

checkCIF report

Comment top

The drug sulfamethazine [4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide] has been used as a model for co-crystal formation (Caira, 2007; Ghosh et al., 2011)), commonly forming 1:1 adducts with carboxylic acids and amides, particularly the benzoic acid analogues. The structures of a number of these are known, including those with 4-nitrobenzoic acid (Smith & Wermuth, 2012) and 2,4-dinitrobenzoic acid (Lynch et al., 2000). In these co-crystals, and in sulfamethazine adducts generally a common structural feature is the cyclic heterodimeric hydrogen-bonding association involving amide N—H···O_carboxyl–carboxylic acid O—H···N_pyrimidine pairs [graph set R²₂(8) (Etter et al., 1990)].

Our 1:1 stoichiometric interaction of sulfamethazine with 2-nitrobenzoic acid gave the co-crystalline adduct C₁₂H₁₄N₄O₂S. C₇H₅NO₄, the title compound and the structure is reported herein. In the sulfamethazine component (Fig. 1) the dihedral angle between the pyrimidine ring and the phenyl ring is 89.98 (18)° which compares with 82.33 (9)° and 78.77 (8)° for the two independent molecules in the 4-nitrobenzoic acid analogue (Smith & Wermuth, 2012). The angles between these two rings and the phenyl ring of the 2-nitrobenzoic acid molecule are 9.65 (19) and 88.22 (19)°, respectively. In the crystal the sulfamethazine and 2-nitrobenzoic acid molecules interact as previously described, giving cyclic R²₂(8) hydrogen-bonded heterodimers (Table 1, Fig. 1).

Intermolecular amine N—H···O_sulfone hydrogen-bonding interactions link the heterodimer units along a (Fig. 2) as well as down b, forming two-dimensional sheet structures which extend along [110]. Unlike the isomeric 4-nitrobenzoic acid adduct there are no π–π interactions present in the structure but there are 52.2 Å³ potential solvent accessible voids present. The oxygen atoms of the nitro group of the adduct acid molecule are rotationally disordered over four 50% occupancy sites [O21, O22 and O23, O24]. In the absence of chirality in the molecules, the Flack absolute structure parameter [0.08 (9)] is of no structural significance.

Related literature top

For background to sulfamethazole as a model for co-crystal formation, see: Caira (2007); Ghosh et al. (2011). For structures of 1:1 adducts of sulfamethazine with nitrobenzoic acid analogues, see: Lynch et al. (2000); Smith & Wermuth (2012). For graph-set analysis, see: Etter et al. (1990).

Experimental top

The title compound was formed in the interaction of 1 mmol quantities of 4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide (sulfamethazine) and 2-nitrobenzoic acid in 50 ml of 50% ethanol–water with 10 min refluxing. Partial evaporation of the solvent gave a pale yellow solid which gave crystal plates suitable for the X-ray analysis after recrystallization from ethanol.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 2012); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular conformation and atom-numbering scheme for the title co-crystal, with inter-species hydrogen bonds shown as a dashed lines. The nitro group of the adduct molecule is 50% rotationally disordered and non-H atoms are shown as 30% probability displacement ellipsoids.
	Fig. 2. A perspective view of the two-dimensional structure which extends along [110], showing hydrogen-bonding associations as dashed lines, with the nitro group disorder not shown.
	Fig. 3. A view of the sheet structure along the b axis.

4-Amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide– 2-nitrobenzoic acid (1/1) top

Crystal data top

C₁₂H₁₄N₄O₂S·C₇H₅NO₄	F(000) = 928
M_r = 445.46	D_x = 1.353 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3011 reflections
a = 14.2945 (4) Å	θ = 3.1–28.8°
b = 8.0115 (3) Å	µ = 0.19 mm⁻¹
c = 19.0962 (5) Å	T = 200 K
V = 2186.91 (12) Å³	Plate, yellow
Z = 4	0.30 × 0.21 × 0.12 mm

Data collection top

Oxford Diffraction Gemini-S CCD-detector diffractometer	2777 independent reflections
Radiation source: Enhance (Mo) X-ray source	2587 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 16.077 pixels mm^-1	θ_max = 26.0°, θ_min = 3.1°
ω scans	h = −17→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −8→9
T_min = 0.964, T_max = 0.980	l = −23→8
5541 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.099	w = 1/[σ²(F_o²) + (0.0555P)² + 0.5356P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
2777 reflections	Δρ_max = 0.29 e Å⁻³
286 parameters	Δρ_min = −0.21 e Å⁻³
29 restraints	Absolute structure: Flack (1983), 565 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (9)

Crystal data top

C₁₂H₁₄N₄O₂S·C₇H₅NO₄	V = 2186.91 (12) Å³
M_r = 445.46	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 14.2945 (4) Å	µ = 0.19 mm⁻¹
b = 8.0115 (3) Å	T = 200 K
c = 19.0962 (5) Å	0.30 × 0.21 × 0.12 mm

Data collection top

Oxford Diffraction Gemini-S CCD-detector diffractometer	2777 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	2587 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.980	R_int = 0.023
5541 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.099	Δρ_max = 0.29 e Å⁻³
S = 1.04	Δρ_min = −0.21 e Å⁻³
2777 reflections	Absolute structure: Flack (1983), 565 Friedel pairs
286 parameters	Absolute structure parameter: 0.08 (9)
29 restraints

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1A	0.44672 (4)	1.02307 (8)	0.75273 (5)	0.0249 (2)
O11A	0.35295 (13)	0.9968 (3)	0.72869 (13)	0.0342 (7)
O12A	0.50151 (14)	1.1513 (3)	0.72083 (12)	0.0326 (7)
N1A	0.47662 (18)	1.1033 (3)	0.95152 (15)	0.0352 (8)
N2A	0.43078 (16)	1.0714 (3)	0.83654 (14)	0.0288 (8)
N3A	0.59047 (17)	1.0898 (3)	0.86027 (15)	0.0334 (8)
N41A	0.65507 (17)	0.3924 (3)	0.7489 (2)	0.0538 (12)
C2A	0.5032 (2)	1.0887 (4)	0.88442 (16)	0.0273 (9)
C4A	0.6585 (2)	1.1028 (4)	0.9085 (2)	0.0392 (11)
C5A	0.6372 (3)	1.1216 (5)	0.9787 (2)	0.0497 (14)
C6A	0.5446 (3)	1.1221 (5)	0.99900 (19)	0.0429 (11)
C11A	0.50792 (17)	0.8370 (3)	0.75032 (18)	0.0262 (8)
C21A	0.60295 (19)	0.8371 (4)	0.73347 (16)	0.0286 (9)
C31A	0.6509 (2)	0.6892 (4)	0.73148 (18)	0.0312 (9)
C41A	0.60616 (19)	0.5374 (3)	0.7475 (2)	0.0324 (9)
C42A	0.7565 (2)	1.0928 (6)	0.8819 (3)	0.0592 (15)
C51A	0.5098 (2)	0.5407 (4)	0.76412 (18)	0.0323 (9)
C61A	0.46169 (19)	0.6885 (4)	0.76475 (17)	0.0289 (9)
C62A	0.5143 (3)	1.1416 (7)	1.0737 (2)	0.0663 (16)
O11	0.28633 (18)	0.8862 (4)	0.90536 (17)	0.0639 (10)
O12	0.30259 (17)	1.0522 (4)	0.99775 (15)	0.0505 (9)
O21	0.2682 (14)	0.800 (3)	1.1121 (18)	0.083 (5)	0.500
O22	0.1915 (11)	1.0471 (16)	1.1479 (5)	0.095 (4)	0.500
O23	0.1968 (11)	0.9621 (18)	1.1692 (5)	0.095 (4)	0.500
O24	0.2837 (14)	0.842 (3)	1.1026 (18)	0.083 (5)	0.500
N2	0.2084 (2)	0.9099 (6)	1.1124 (2)	0.0668 (14)
C1	0.1619 (2)	0.9013 (4)	0.98691 (19)	0.0378 (10)
C2	0.1370 (2)	0.8973 (5)	1.05718 (19)	0.0408 (11)
C3	0.0460 (2)	0.8689 (5)	1.0792 (2)	0.0503 (14)
C4	−0.0216 (3)	0.8434 (6)	1.0290 (3)	0.0613 (16)
C5	0.0011 (3)	0.8421 (7)	0.9596 (3)	0.0680 (18)
C6	0.0926 (3)	0.8725 (6)	0.9385 (2)	0.0580 (14)
C11	0.2569 (2)	0.9455 (5)	0.95931 (19)	0.0387 (11)
H2A	0.37560	1.03330	0.85240	0.0350*
H5A	0.68450	1.13390	1.01170	0.0600*
H21A	0.63350	0.93690	0.72370	0.0340*
H31A	0.71390	0.68900	0.71940	0.0380*
H41A	0.71650	0.38280	0.73590	0.0650*
H42A	0.62490	0.30460	0.75470	0.0650*
H43A	0.78730	0.99840	0.90250	0.0890*
H44A	0.78950	1.19300	0.89420	0.0890*
H45A	0.75570	1.08070	0.83190	0.0890*
H51A	0.47880	0.44180	0.77470	0.0390*
H61A	0.39800	0.68950	0.77480	0.0350*
H62A	0.44730	1.13730	1.07620	0.0990*
H63A	0.53580	1.24710	1.09130	0.0990*
H64A	0.54040	1.05310	1.10130	0.0990*
H3	0.03110	0.86720	1.12660	0.0600*
H4	−0.08350	0.82690	1.04260	0.0740*
H5	−0.04480	0.82070	0.92630	0.0820*
H6	0.10710	0.87350	0.89100	0.0690*
H12	0.36150	1.06900	0.98230	0.0760*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1A	0.0215 (3)	0.0274 (3)	0.0259 (3)	0.0012 (2)	−0.0003 (3)	−0.0001 (4)
O11A	0.0246 (10)	0.0395 (11)	0.0385 (13)	0.0037 (8)	−0.0055 (10)	−0.0031 (10)
O12A	0.0320 (11)	0.0301 (11)	0.0357 (12)	−0.0002 (8)	0.0019 (10)	0.0056 (11)
N1A	0.0352 (14)	0.0415 (16)	0.0289 (14)	−0.0063 (12)	0.0044 (12)	−0.0024 (13)
N2A	0.0196 (12)	0.0357 (13)	0.0312 (14)	−0.0001 (10)	0.0047 (11)	−0.0042 (12)
N3A	0.0287 (13)	0.0381 (15)	0.0334 (15)	−0.0045 (11)	0.0021 (12)	−0.0023 (13)
N41A	0.0292 (12)	0.0281 (13)	0.104 (3)	0.0001 (10)	0.0144 (19)	0.000 (2)
C2A	0.0290 (15)	0.0261 (15)	0.0267 (16)	−0.0033 (12)	0.0013 (13)	−0.0014 (13)
C4A	0.0333 (17)	0.0414 (18)	0.043 (2)	−0.0065 (14)	−0.0031 (17)	−0.0012 (17)
C5A	0.047 (2)	0.063 (3)	0.039 (2)	−0.0157 (18)	−0.0120 (18)	0.003 (2)
C6A	0.048 (2)	0.050 (2)	0.0306 (18)	−0.0159 (17)	0.0001 (16)	−0.0002 (17)
C11A	0.0234 (12)	0.0310 (14)	0.0242 (13)	0.0008 (10)	−0.0014 (14)	−0.0014 (15)
C21A	0.0236 (13)	0.0308 (14)	0.0314 (17)	−0.0061 (11)	0.0053 (12)	0.0009 (13)
C31A	0.0209 (13)	0.0333 (15)	0.0395 (19)	0.0001 (11)	0.0049 (13)	−0.0029 (14)
C41A	0.0264 (13)	0.0318 (14)	0.0391 (17)	−0.0005 (11)	0.0013 (17)	0.0005 (17)
C42A	0.0316 (19)	0.079 (3)	0.067 (3)	−0.007 (2)	−0.006 (2)	−0.008 (3)
C51A	0.0278 (14)	0.0282 (14)	0.041 (2)	−0.0072 (11)	0.0010 (15)	−0.0015 (15)
C61A	0.0190 (12)	0.0346 (15)	0.033 (2)	−0.0056 (10)	0.0014 (13)	−0.0021 (14)
C62A	0.080 (3)	0.090 (3)	0.029 (2)	−0.017 (3)	0.001 (2)	−0.004 (2)
O11	0.0497 (15)	0.092 (2)	0.0499 (18)	−0.0238 (14)	0.0210 (14)	−0.0240 (17)
O12	0.0360 (13)	0.0713 (17)	0.0443 (16)	−0.0111 (12)	0.0148 (12)	−0.0126 (15)
O21	0.054 (6)	0.123 (10)	0.073 (8)	0.001 (7)	−0.004 (4)	0.065 (6)
O22	0.060 (3)	0.186 (12)	0.039 (5)	−0.011 (7)	0.000 (5)	−0.033 (6)
O23	0.060 (3)	0.186 (12)	0.039 (5)	−0.011 (7)	0.000 (5)	−0.033 (6)
O24	0.054 (6)	0.123 (10)	0.073 (8)	0.001 (7)	−0.004 (4)	0.065 (6)
N2	0.0385 (19)	0.125 (3)	0.037 (2)	−0.011 (2)	0.0077 (17)	0.001 (2)
C1	0.0342 (16)	0.046 (2)	0.0333 (18)	−0.0038 (14)	0.0065 (16)	0.0044 (17)
C2	0.0335 (17)	0.052 (2)	0.037 (2)	−0.0019 (15)	0.0062 (16)	0.0041 (17)
C3	0.043 (2)	0.070 (3)	0.038 (2)	−0.0094 (18)	0.0142 (18)	0.003 (2)
C4	0.036 (2)	0.088 (3)	0.060 (3)	−0.020 (2)	0.010 (2)	−0.001 (3)
C5	0.042 (2)	0.113 (4)	0.049 (3)	−0.023 (2)	−0.008 (2)	0.006 (3)
C6	0.043 (2)	0.096 (3)	0.035 (2)	−0.015 (2)	0.0038 (17)	0.005 (2)
C11	0.0347 (18)	0.048 (2)	0.0335 (19)	−0.0029 (15)	0.0057 (16)	−0.0002 (17)

Geometric parameters (Å, º) top

S1A—O11A	1.432 (2)	C21A—C31A	1.369 (4)
S1A—O12A	1.428 (2)	C31A—C41A	1.408 (4)
S1A—N2A	1.662 (3)	C41A—C51A	1.414 (4)
S1A—C11A	1.729 (2)	C51A—C61A	1.369 (4)
O11—C11	1.210 (5)	C5A—H5A	0.9300
O12—C11	1.302 (5)	C21A—H21A	0.9300
O21—N2	1.23 (2)	C31A—H31A	0.9300
O22—N2	1.314 (13)	C42A—H45A	0.9600
O23—N2	1.174 (11)	C42A—H43A	0.9600
O24—N2	1.22 (2)	C42A—H44A	0.9600
O12—H12	0.9000	C51A—H51A	0.9300
N1A—C6A	1.338 (5)	C61A—H61A	0.9300
N1A—C2A	1.342 (4)	C62A—H62A	0.9600
N2A—C2A	1.388 (4)	C62A—H63A	0.9600
N3A—C2A	1.330 (4)	C62A—H64A	0.9600
N3A—C4A	1.343 (4)	C1—C6	1.375 (5)
N41A—C41A	1.356 (3)	C1—C11	1.499 (4)
N2A—H2A	0.9000	C1—C2	1.389 (5)
N41A—H41A	0.9200	C2—C3	1.386 (4)
N41A—H42A	0.8300	C3—C4	1.376 (6)
N2—C2	1.471 (5)	C4—C5	1.365 (8)
C4A—C42A	1.492 (4)	C5—C6	1.390 (6)
C4A—C5A	1.383 (5)	C3—H3	0.9300
C5A—C6A	1.379 (6)	C4—H4	0.9300
C6A—C62A	1.499 (5)	C5—H5	0.9300
C11A—C21A	1.396 (4)	C6—H6	0.9300
C11A—C61A	1.389 (4)

O11A—S1A—O12A	118.83 (14)	C11A—C21A—H21A	120.00
O11A—S1A—N2A	102.39 (13)	C31A—C21A—H21A	120.00
O11A—S1A—C11A	109.77 (13)	C21A—C31A—H31A	120.00
O12A—S1A—N2A	108.56 (13)	C41A—C31A—H31A	120.00
O12A—S1A—C11A	109.35 (13)	H43A—C42A—H44A	109.00
N2A—S1A—C11A	107.21 (15)	C4A—C42A—H44A	109.00
C2A—N1A—C6A	116.8 (3)	C4A—C42A—H43A	109.00
S1A—N2A—C2A	123.7 (2)	H44A—C42A—H45A	109.00
C2A—N3A—C4A	116.2 (3)	H43A—C42A—H45A	109.00
C2A—N2A—H2A	118.00	C4A—C42A—H45A	109.00
S1A—N2A—H2A	111.00	C61A—C51A—H51A	120.00
C41A—N41A—H41A	124.00	C41A—C51A—H51A	120.00
H41A—N41A—H42A	118.00	C11A—C61A—H61A	120.00
C41A—N41A—H42A	117.00	C51A—C61A—H61A	120.00
O24—N2—C2	118.1 (16)	H63A—C62A—H64A	110.00
O23—N2—C2	126.1 (8)	C6A—C62A—H62A	109.00
O21—N2—O22	137.0 (16)	C6A—C62A—H63A	109.00
O21—N2—C2	115.5 (15)	H62A—C62A—H63A	109.00
O22—N2—C2	107.4 (7)	H62A—C62A—H64A	110.00
N1A—C2A—N3A	126.6 (3)	C6A—C62A—H64A	109.00
N1A—C2A—N2A	115.3 (3)	C2—C1—C11	125.3 (3)
N2A—C2A—N3A	118.2 (3)	C6—C1—C11	117.1 (3)
N3A—C4A—C5A	120.9 (3)	C2—C1—C6	117.5 (3)
C5A—C4A—C42A	122.9 (4)	N2—C2—C3	116.4 (3)
N3A—C4A—C42A	116.2 (4)	C1—C2—C3	122.5 (3)
C4A—C5A—C6A	119.0 (4)	N2—C2—C1	120.9 (3)
N1A—C6A—C5A	120.4 (3)	C2—C3—C4	118.2 (4)
N1A—C6A—C62A	116.6 (4)	C3—C4—C5	120.7 (4)
C5A—C6A—C62A	123.0 (4)	C4—C5—C6	120.3 (4)
C21A—C11A—C61A	120.6 (2)	C1—C6—C5	120.8 (4)
S1A—C11A—C61A	119.5 (2)	O11—C11—C1	121.4 (3)
S1A—C11A—C21A	119.9 (2)	O12—C11—C1	114.3 (3)
C11A—C21A—C31A	119.5 (3)	O11—C11—O12	124.3 (3)
C21A—C31A—C41A	120.9 (3)	C2—C3—H3	121.00
C31A—C41A—C51A	118.4 (2)	C4—C3—H3	121.00
N41A—C41A—C31A	120.7 (3)	C3—C4—H4	120.00
N41A—C41A—C51A	120.9 (3)	C5—C4—H4	120.00
C41A—C51A—C61A	120.5 (3)	C4—C5—H5	120.00
C11A—C61A—C51A	120.0 (3)	C6—C5—H5	120.00
C4A—C5A—H5A	121.00	C1—C6—H6	120.00
C6A—C5A—H5A	120.00	C5—C6—H6	120.00

O11A—S1A—N2A—C2A	172.1 (2)	O23—N2—C2—C3	−31.7 (11)
O12A—S1A—N2A—C2A	−61.5 (3)	O24—N2—C2—C1	−36.8 (15)
C11A—S1A—N2A—C2A	56.6 (3)	O24—N2—C2—C3	138.5 (14)
O11A—S1A—C11A—C21A	145.0 (3)	O22—N2—C2—C3	−67.6 (7)
O11A—S1A—C11A—C61A	−34.6 (3)	O23—N2—C2—C1	153.1 (9)
O12A—S1A—C11A—C21A	13.0 (3)	C42A—C4A—C5A—C6A	−177.1 (4)
O12A—S1A—C11A—C61A	−166.6 (3)	N3A—C4A—C5A—C6A	1.8 (5)
N2A—S1A—C11A—C21A	−104.5 (3)	C4A—C5A—C6A—N1A	0.5 (6)
N2A—S1A—C11A—C61A	75.9 (3)	C4A—C5A—C6A—C62A	180.0 (4)
O24—O21—N2—O23	−106 (6)	C61A—C11A—C21A—C31A	−0.3 (5)
O24—O21—N2—C2	102 (6)	S1A—C11A—C61A—C51A	−178.9 (3)
O24—O21—N2—O22	−74 (7)	S1A—C11A—C21A—C31A	−179.8 (3)
O23—O22—N2—C2	127.6 (15)	C21A—C11A—C61A—C51A	1.5 (5)
O23—O22—N2—O21	−56 (3)	C11A—C21A—C31A—C41A	−1.2 (5)
O23—O22—N2—O24	−82 (3)	C21A—C31A—C41A—N41A	−176.6 (3)
O22—O23—N2—C2	−69.3 (18)	C21A—C31A—C41A—C51A	1.5 (5)
O22—O23—N2—O24	120 (2)	C31A—C41A—C51A—C61A	−0.2 (5)
O22—O23—N2—O21	142.5 (18)	N41A—C41A—C51A—C61A	177.9 (3)
O21—O24—N2—O22	124 (5)	C41A—C51A—C61A—C11A	−1.3 (5)
O21—O24—N2—O23	83 (6)	C6—C1—C2—N2	173.8 (4)
O21—O24—N2—C2	−88 (6)	C6—C1—C2—C3	−1.2 (6)
C2A—N1A—C6A—C62A	178.9 (4)	C11—C1—C2—N2	−10.5 (6)
C6A—N1A—C2A—N2A	−179.3 (3)	C11—C1—C2—C3	174.5 (4)
C6A—N1A—C2A—N3A	0.5 (5)	C2—C1—C6—C5	0.6 (6)
C2A—N1A—C6A—C5A	−1.7 (5)	C11—C1—C6—C5	−175.6 (4)
S1A—N2A—C2A—N1A	−170.5 (2)	C2—C1—C11—O11	149.7 (4)
S1A—N2A—C2A—N3A	9.7 (4)	C2—C1—C11—O12	−30.9 (5)
C4A—N3A—C2A—N2A	−178.5 (3)	C6—C1—C11—O11	−34.5 (5)
C2A—N3A—C4A—C5A	−2.9 (5)	C6—C1—C11—O12	144.8 (4)
C4A—N3A—C2A—N1A	1.8 (5)	N2—C2—C3—C4	−175.0 (4)
C2A—N3A—C4A—C42A	176.1 (3)	C1—C2—C3—C4	0.2 (6)
O21—N2—C2—C3	115.3 (15)	C2—C3—C4—C5	1.6 (7)
O22—N2—C2—C1	117.1 (7)	C3—C4—C5—C6	−2.3 (8)
O21—N2—C2—C1	−60.0 (15)	C4—C5—C6—C1	1.2 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12···N1A	0.90	1.77	2.671 (4)	180
N2A—H2A···O11	0.90	2.01	2.862 (4)	158
N41A—H41A···O11Aⁱ	0.92	2.18	2.990 (3)	147
N41A—H42A···O12Aⁱⁱ	0.83	2.24	2.973 (3)	146
C3—H3···O12Aⁱⁱⁱ	0.93	2.54	3.289 (4)	138
C21A—H21A···O12A	0.93	2.55	2.915 (4)	104
C31A—H31A···O11Aⁱ	0.93	2.49	3.250 (4)	139
C51A—H51A···O12Aⁱⁱ	0.93	2.57	3.230 (4)	129

Symmetry codes: (i) x+1/2, −y+3/2, z; (ii) x, y−1, z; (iii) −x+1/2, y−1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₄N₄O₂S·C₇H₅NO₄
M_r	445.46
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	200
a, b, c (Å)	14.2945 (4), 8.0115 (3), 19.0962 (5)
V (Å³)	2186.91 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.30 × 0.21 × 0.12

Data collection
Diffractometer	Oxford Diffraction Gemini-S CCD-detector diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.964, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	5541, 2777, 2587
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.099, 1.04
No. of reflections	2777
No. of parameters	286
No. of restraints	29
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.21
Absolute structure	Flack (1983), 565 Friedel pairs
Absolute structure parameter	0.08 (9)

Computer programs: CrysAlis PRO (Agilent, 2012), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 2012), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12···N1A	0.90	1.77	2.671 (4)	180
N2A—H2A···O11	0.90	2.01	2.862 (4)	158
N41A—H41A···O11Aⁱ	0.92	2.18	2.990 (3)	147
N41A—H42A···O12Aⁱⁱ	0.83	2.24	2.973 (3)	146

Symmetry codes: (i) x+1/2, −y+3/2, z; (ii) x, y−1, z.

Acknowledgements

The authors acknowledge financial support from the Australian Reseach Council and the Science and Engineering Faculty and the University Library, Queensland University of Technology.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England. Google Scholar
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Caira, M. R. (2007). Mol. Pharm. 4, 310–316. Web of Science CrossRef PubMed CAS Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ghosh, S., Bag, P. P. & Reddy, C. M. (2011). Cryst. Growth Des. 11, 3489–3503. Web of Science CSD CrossRef CAS Google Scholar
Lynch, D. E., Sandhu, P. & Parsons, S. (2000). Aust. J. Chem. 53, 383–387. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Smith, G. & Wermuth, U. D. (2012). Acta Cryst. E68, o1649–o1650. CSD CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-Amino-N-(4,6-di­methyl­pyrimidin-2-yl)benzene­sulfonamide–2-nitro­benzoic acid (1/1)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-Amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide–2-nitrobenzoic acid (1/1)