4-Chloro-2-nitro-benzoic acid-pyrazine (2/1).

In the title co-crystal, 2C(7)H(4)ClNO(4)·C(4)H(4)N(2), the pyrazine mol-ecule is located on an inversion centre, so that the asymmetric unit consists of one mol-ecule of 4-chloro-2-nitro-benzoic acid and a half-mol-ecule of pyrazine. The components are connected by O-H⋯N and C-H⋯O hydrogen bonds, forming a 2:1 unit. In the hydrogen-bonded unit, the dihedral angle between the pyrazine ring and the benzene ring of the benzoic acid is 16.55 (4)°. The units are linked by inter-molecular C-H⋯O hydrogen bonds, forming a sheet structure parallel to ([Formula: see text]04). A C-H⋯O hydrogen-bond linkage is also observed between these sheets.

Related literature

For related structures, see: Gotoh & Ishida (2009 ▶); Gotoh et al. (2010 ▶); Ishida et al. (2001 ▶).

Experimental

Crystal data

2C7H4ClNO4·C4H4N2

M = 483.22

Monoclinic,

a = 4.87662 (13) Å

b = 13.5385 (3) Å

c = 14.7981 (6) Å

β = 90.858 (2)°

V = 976.89 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.39 mm−1

T = 110 K

0.35 × 0.15 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID II diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.904, T max = 0.958

19734 measured reflections

2833 independent reflections

2535 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.081

S = 1.07

2833 reflections

149 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.51 e Å−3

Δρmin = −0.39 e Å−3

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811046113/fj2468sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046113/fj2468Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811046113/fj2468Isup3.cml

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

2C7H4ClNO4·C4H4N2	F(000) = 492.00
Mr = 483.22	Dx = 1.643 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 16875 reflections
a = 4.87662 (13) Å	θ = 3.0–30.1°
b = 13.5385 (3) Å	µ = 0.39 mm−1
c = 14.7981 (6) Å	T = 110 K
β = 90.858 (2)°	Block, colorless
V = 976.89 (5) Å3	0.35 × 0.15 × 0.11 mm
Z = 2

Rigaku R-AXIS RAPID II diffractometer	2535 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1	Rint = 0.032
ω scans	θmax = 30.0°
Absorption correction: numerical (NUMABS; Higashi, 1999)	h = −6→6
Tmin = 0.904, Tmax = 0.958	k = −19→19
19734 measured reflections	l = −20→20
2833 independent 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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0499P)2 + 0.2334P] where P = (Fo2 + 2Fc2)/3
2833 reflections	(Δ/σ)max = 0.001
149 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.39 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
Cl1	1.52398 (5)	0.692432 (19)	0.490381 (17)	0.02257 (8)
O1	0.69354 (15)	0.47150 (5)	0.18863 (5)	0.02033 (15)
O2	0.54429 (14)	0.62747 (5)	0.17436 (5)	0.01875 (15)
O3	0.99168 (16)	0.77178 (6)	0.14572 (5)	0.02218 (16)
O4	0.72288 (16)	0.82806 (6)	0.25018 (5)	0.02337 (17)
N1	0.89159 (16)	0.76980 (6)	0.22167 (5)	0.01549 (16)
N2	0.18864 (16)	0.54745 (6)	0.05617 (5)	0.01577 (16)
C1	0.90441 (18)	0.59589 (7)	0.27806 (6)	0.01446 (17)
C2	0.99232 (19)	0.69339 (6)	0.28474 (6)	0.01377 (17)
C3	1.18351 (19)	0.72540 (7)	0.34825 (6)	0.01557 (18)
H3	1.2416	0.7923	0.3504	0.019*
C4	1.28706 (19)	0.65599 (7)	0.40871 (7)	0.01698 (18)
C5	1.2038 (2)	0.55818 (7)	0.40559 (7)	0.01984 (19)
H5	1.2757	0.5117	0.4478	0.024*
C6	1.0143 (2)	0.52883 (7)	0.34015 (7)	0.01845 (19)
H6	0.9584	0.4617	0.3376	0.022*
C7	0.70336 (18)	0.55797 (7)	0.20900 (6)	0.01475 (17)
C8	0.18281 (19)	0.44916 (7)	0.04969 (6)	0.01661 (18)
H8	0.3099	0.4109	0.0841	0.020*
C9	0.00621 (19)	0.59808 (7)	0.00657 (6)	0.01588 (18)
H9	0.0056	0.6682	0.0098	0.019*
H2	0.429 (4)	0.6024 (14)	0.1346 (14)	0.050 (5)*

	U11	U22	U33	U12	U13	U23
Cl1	0.02064 (13)	0.02541 (14)	0.02136 (13)	−0.00126 (9)	−0.00925 (9)	−0.00274 (9)
O1	0.0212 (3)	0.0153 (3)	0.0243 (4)	−0.0027 (3)	−0.0041 (3)	−0.0039 (3)
O2	0.0174 (3)	0.0171 (3)	0.0215 (4)	0.0001 (3)	−0.0072 (3)	−0.0038 (3)
O3	0.0290 (4)	0.0224 (4)	0.0151 (3)	−0.0004 (3)	0.0005 (3)	0.0007 (3)
O4	0.0249 (4)	0.0182 (3)	0.0271 (4)	0.0068 (3)	0.0004 (3)	−0.0010 (3)
N1	0.0167 (4)	0.0131 (3)	0.0166 (4)	−0.0019 (3)	−0.0031 (3)	−0.0010 (3)
N2	0.0148 (3)	0.0181 (4)	0.0144 (4)	−0.0023 (3)	−0.0012 (3)	−0.0013 (3)
C1	0.0139 (4)	0.0135 (4)	0.0160 (4)	−0.0009 (3)	−0.0011 (3)	−0.0025 (3)
C2	0.0138 (4)	0.0135 (4)	0.0139 (4)	0.0011 (3)	−0.0007 (3)	−0.0008 (3)
C3	0.0150 (4)	0.0150 (4)	0.0167 (4)	−0.0015 (3)	−0.0012 (3)	−0.0025 (3)
C4	0.0146 (4)	0.0199 (4)	0.0163 (4)	0.0005 (3)	−0.0037 (3)	−0.0024 (3)
C5	0.0207 (4)	0.0179 (4)	0.0208 (4)	0.0015 (4)	−0.0059 (4)	0.0014 (4)
C6	0.0200 (4)	0.0138 (4)	0.0215 (4)	−0.0005 (3)	−0.0036 (3)	−0.0002 (3)
C7	0.0131 (4)	0.0160 (4)	0.0151 (4)	−0.0022 (3)	0.0002 (3)	−0.0017 (3)
C8	0.0160 (4)	0.0178 (4)	0.0159 (4)	−0.0004 (3)	−0.0019 (3)	−0.0006 (3)
C9	0.0165 (4)	0.0154 (4)	0.0157 (4)	−0.0017 (3)	−0.0003 (3)	−0.0010 (3)

Cl1—C4	1.7313 (10)	C2—C3	1.3836 (12)
O1—C7	1.2095 (11)	C3—C4	1.3875 (13)
O2—C7	1.3183 (11)	C3—H3	0.9500
O2—H2	0.88 (2)	C4—C5	1.3855 (14)
O3—N1	1.2323 (11)	C5—C6	1.3866 (13)
O4—N1	1.2195 (11)	C5—H5	0.9500
N1—C2	1.4727 (12)	C6—H6	0.9500
N2—C9	1.3343 (12)	C8—C9i	1.3888 (13)
N2—C8	1.3344 (13)	C8—H8	0.9500
C1—C2	1.3909 (12)	C9—C8i	1.3888 (13)
C1—C6	1.3932 (13)	C9—H9	0.9500
C1—C7	1.4964 (12)
C7—O2—H2	110.7 (12)	C3—C4—Cl1	119.32 (7)
O4—N1—O3	125.45 (9)	C4—C5—C6	119.28 (9)
O4—N1—C2	117.09 (8)	C4—C5—H5	120.4
O3—N1—C2	117.41 (8)	C6—C5—H5	120.4
C9—N2—C8	117.35 (8)	C5—C6—C1	121.31 (9)
C2—C1—C6	117.15 (8)	C5—C6—H6	119.3
C2—C1—C7	124.91 (8)	C1—C6—H6	119.3
C6—C1—C7	117.93 (8)	O1—C7—O2	124.96 (9)
C3—C2—C1	123.33 (8)	O1—C7—C1	121.69 (9)
C3—C2—N1	115.18 (8)	O2—C7—C1	113.35 (8)
C1—C2—N1	121.47 (8)	N2—C8—C9i	121.03 (8)
C2—C3—C4	117.45 (9)	N2—C8—H8	119.5
C2—C3—H3	121.3	C9i—C8—H8	119.5
C4—C3—H3	121.3	N2—C9—C8i	121.62 (9)
C5—C4—C3	121.48 (9)	N2—C9—H9	119.2
C5—C4—Cl1	119.20 (7)	C8i—C9—H9	119.2
C6—C1—C2—C3	1.03 (14)	C3—C4—C5—C6	0.51 (15)
C7—C1—C2—C3	−178.46 (9)	Cl1—C4—C5—C6	−179.92 (8)
C6—C1—C2—N1	179.18 (9)	C4—C5—C6—C1	−0.57 (15)
C7—C1—C2—N1	−0.31 (14)	C2—C1—C6—C5	−0.16 (15)
O4—N1—C2—C3	−77.08 (11)	C7—C1—C6—C5	179.36 (9)
O3—N1—C2—C3	100.39 (10)	C2—C1—C7—O1	157.90 (10)
O4—N1—C2—C1	104.62 (10)	C6—C1—C7—O1	−21.58 (14)
O3—N1—C2—C1	−77.91 (11)	C2—C1—C7—O2	−22.11 (13)
C1—C2—C3—C4	−1.09 (14)	C6—C1—C7—O2	158.41 (9)
N1—C2—C3—C4	−179.35 (8)	C9—N2—C8—C9i	−0.01 (15)
C2—C3—C4—C5	0.29 (15)	C8—N2—C9—C8i	0.01 (15)
C2—C3—C4—Cl1	−179.28 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.88 (2)	1.80 (2)	2.6739 (10)	178 (2)
C3—H3···O1ii	0.95	2.51	3.4305 (12)	162
C6—H6···O3iii	0.95	2.59	3.4865 (13)	157
C8—H8···O1	0.95	2.55	3.2201 (12)	128
C9—H9···O3iv	0.95	2.45	3.1273 (12)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2	0.88 (2)	1.80 (2)	2.6739 (10)	178 (2)
C3—H3⋯O1i	0.95	2.51	3.4305 (12)	162
C6—H6⋯O3ii	0.95	2.59	3.4865 (13)	157
C8—H8⋯O1	0.95	2.55	3.2201 (12)	128
C9—H9⋯O3iii	0.95	2.45	3.1273 (12)	128

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