Benzamide-picric acid (1/1).

In the title compound, C(7)H(7)NO·C(6)H(3)N(3)O(7), one of the nitro groups of the picric acid mol-ecule lies in the plane of the attached benzene ring [dihedral angle = 1.4 (1)°] while the other two are twisted away by 9.9 (1) and 30.3 (1)°. In the benzamide mol-ecule, the amide group is almost coplanar with the benzene ring [dihedral angle = 4.4 (1)°]. An intra-molecular O-H⋯O hydrogen bond generates an S6 ring motif. In the crystal, mol-ecules are linked into a ribbon-like structure along the b axis by O-H⋯O and N-H⋯O inter-molecular hydrogen bonds. In addition, C-H⋯O hydrogen bonds and short O⋯O contacts [2.828 (2) Å] are observed.

Related literature

For crystal structures of picric acid complexes, see: In et al. (1997 ▶); Zaderenko et al. (1997 ▶); Nagata et al. (1995 ▶); Smith et al. (2004 ▶); Goto et al. (2004 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C7H7NO·C6H3N3O7

M = 350.25

Monoclinic,

a = 7.8644 (3) Å

b = 7.0664 (3) Å

c = 25.658 (1) Å

β = 90.978 (4)°

V = 1425.68 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 110 K

0.22 × 0.19 × 0.17 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.970, T max = 0.977

8136 measured reflections

3309 independent reflections

2518 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.102

S = 1.03

3309 reflections

238 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024232/ci5096sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024232/ci5096Isup2.hkl

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

C7H7NO·C6H3N3O7	F(000) = 720
Mr = 350.25	Dx = 1.632 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1043 reflections
a = 7.8644 (3) Å	θ = 3.0–29.2°
b = 7.0664 (3) Å	µ = 0.14 mm−1
c = 25.658 (1) Å	T = 110 K
β = 90.978 (4)°	Block, colourless
V = 1425.68 (10) Å3	0.22 × 0.19 × 0.17 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	3309 independent reflections
Radiation source: fine-focus sealed tube	2518 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω and φ scans	θmax = 29.2°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→10
Tmin = 0.970, Tmax = 0.977	k = −9→9
8136 measured reflections	l = −33→32

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0535P)2 + 0.2776P] where P = (Fo2 + 2Fc2)/3
3309 reflections	(Δ/σ)max = 0.011
238 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.27 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
O1	0.26955 (15)	0.56145 (16)	0.32065 (4)	0.0186 (3)
H1	0.234 (3)	0.606 (4)	0.2877 (10)	0.065 (8)*
O2	0.27599 (15)	0.83691 (16)	0.25079 (4)	0.0217 (3)
O3	0.45097 (16)	1.06988 (18)	0.26121 (5)	0.0302 (3)
O4	0.70184 (17)	1.20512 (18)	0.42672 (5)	0.0335 (3)
O5	0.68930 (15)	0.99973 (18)	0.48912 (4)	0.0252 (3)
O6	0.32595 (16)	0.46474 (17)	0.46982 (4)	0.0249 (3)
O7	0.32915 (16)	0.32061 (16)	0.39538 (5)	0.0259 (3)
N1	0.38210 (17)	0.92648 (19)	0.27671 (5)	0.0179 (3)
N2	0.65720 (17)	1.0525 (2)	0.44464 (5)	0.0203 (3)
N3	0.35066 (16)	0.46102 (18)	0.42288 (5)	0.0166 (3)
C1	0.36450 (19)	0.6822 (2)	0.34693 (6)	0.0144 (3)
C2	0.4245 (2)	0.8595 (2)	0.32927 (6)	0.0148 (3)
C3	0.5215 (2)	0.9797 (2)	0.36018 (6)	0.0167 (3)
H3	0.5615	1.0967	0.3469	0.020*
C4	0.5587 (2)	0.9257 (2)	0.41060 (6)	0.0163 (3)
C5	0.5038 (2)	0.7559 (2)	0.43079 (6)	0.0156 (3)
H5	0.5297	0.7220	0.4659	0.019*
C6	0.41086 (19)	0.6370 (2)	0.39906 (6)	0.0145 (3)
O8	0.10176 (16)	0.49021 (16)	0.23654 (4)	0.0223 (3)
N4	−0.05714 (19)	0.6826 (2)	0.18599 (6)	0.0213 (3)
H4A	−0.103 (3)	0.705 (3)	0.1554 (9)	0.039 (6)*
H4B	−0.060 (3)	0.766 (3)	0.2127 (8)	0.034 (6)*
C7	0.0404 (2)	0.3810 (2)	0.15103 (6)	0.0156 (3)
C8	0.1221 (2)	0.2114 (2)	0.16244 (6)	0.0180 (3)
H8	0.1681	0.1906	0.1964	0.022*
C9	0.1373 (2)	0.0724 (2)	0.12491 (6)	0.0211 (4)
H9	0.1930	−0.0433	0.1332	0.025*
C10	0.0710 (2)	0.1023 (2)	0.07508 (6)	0.0231 (4)
H10	0.0818	0.0072	0.0492	0.028*
C11	−0.0112 (2)	0.2708 (2)	0.06315 (6)	0.0221 (4)
H11	−0.0566	0.2910	0.0291	0.026*
C12	−0.0273 (2)	0.4104 (2)	0.10097 (6)	0.0187 (3)
H12	−0.0842	0.5255	0.0928	0.022*
C13	0.0304 (2)	0.5238 (2)	0.19409 (6)	0.0162 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0225 (6)	0.0159 (6)	0.0172 (6)	−0.0032 (5)	−0.0053 (4)	0.0010 (4)
O2	0.0253 (6)	0.0198 (6)	0.0198 (6)	−0.0010 (5)	−0.0075 (5)	0.0011 (5)
O3	0.0324 (7)	0.0296 (7)	0.0285 (7)	−0.0124 (6)	−0.0014 (5)	0.0119 (5)
O4	0.0418 (8)	0.0196 (7)	0.0387 (8)	−0.0148 (6)	−0.0071 (6)	0.0005 (5)
O5	0.0269 (7)	0.0276 (7)	0.0210 (6)	−0.0035 (6)	−0.0044 (5)	−0.0051 (5)
O6	0.0320 (7)	0.0247 (7)	0.0180 (6)	−0.0040 (6)	−0.0008 (5)	0.0045 (5)
O7	0.0372 (7)	0.0128 (6)	0.0273 (6)	−0.0005 (6)	−0.0080 (5)	−0.0008 (5)
N1	0.0181 (7)	0.0170 (7)	0.0188 (7)	0.0025 (6)	0.0019 (5)	0.0022 (5)
N2	0.0191 (7)	0.0179 (7)	0.0237 (7)	−0.0022 (6)	−0.0002 (5)	−0.0053 (6)
N3	0.0158 (7)	0.0133 (7)	0.0206 (7)	0.0001 (6)	−0.0046 (5)	0.0014 (5)
C1	0.0127 (7)	0.0139 (7)	0.0167 (7)	0.0022 (7)	0.0003 (6)	−0.0019 (6)
C2	0.0145 (7)	0.0160 (8)	0.0141 (7)	0.0031 (7)	0.0008 (6)	0.0007 (6)
C3	0.0158 (8)	0.0126 (7)	0.0218 (8)	0.0010 (7)	0.0034 (6)	−0.0006 (6)
C4	0.0145 (8)	0.0154 (8)	0.0191 (7)	−0.0014 (7)	0.0003 (6)	−0.0048 (6)
C5	0.0155 (8)	0.0163 (8)	0.0149 (7)	0.0031 (7)	−0.0017 (6)	−0.0015 (6)
C6	0.0145 (8)	0.0117 (7)	0.0174 (7)	0.0017 (6)	0.0009 (6)	0.0004 (6)
O8	0.0302 (7)	0.0170 (6)	0.0196 (6)	−0.0018 (5)	−0.0092 (5)	0.0007 (5)
N4	0.0293 (8)	0.0154 (7)	0.0190 (7)	0.0035 (7)	−0.0040 (6)	−0.0007 (6)
C7	0.0132 (7)	0.0158 (8)	0.0180 (7)	−0.0034 (6)	0.0005 (6)	0.0011 (6)
C8	0.0161 (8)	0.0179 (8)	0.0201 (8)	−0.0014 (7)	0.0006 (6)	0.0030 (6)
C9	0.0214 (8)	0.0161 (8)	0.0260 (9)	0.0015 (7)	0.0042 (7)	0.0023 (6)
C10	0.0228 (9)	0.0230 (9)	0.0237 (8)	−0.0016 (8)	0.0035 (7)	−0.0068 (7)
C11	0.0202 (9)	0.0275 (9)	0.0185 (8)	−0.0009 (8)	−0.0024 (6)	−0.0015 (7)
C12	0.0156 (8)	0.0193 (8)	0.0211 (8)	−0.0002 (7)	−0.0008 (6)	0.0018 (6)
C13	0.0163 (8)	0.0139 (8)	0.0183 (8)	−0.0045 (7)	−0.0008 (6)	0.0024 (6)

O1—C1	1.3126 (19)	C5—H5	0.95
O1—H1	0.94 (3)	O8—C13	1.2399 (19)
O2—N1	1.2330 (17)	N4—C13	1.331 (2)
O3—N1	1.2189 (17)	N4—H4A	0.87 (2)
O4—N2	1.2262 (18)	N4—H4B	0.90 (2)
O5—N2	1.2230 (18)	C7—C8	1.389 (2)
O6—N3	1.2237 (17)	C7—C12	1.397 (2)
O7—N3	1.2275 (17)	C7—C13	1.499 (2)
N1—C2	1.4623 (19)	C8—C9	1.382 (2)
N2—C4	1.464 (2)	C8—H8	0.95
N3—C6	1.468 (2)	C9—C10	1.389 (2)
C1—C2	1.416 (2)	C9—H9	0.95
C1—C6	1.417 (2)	C10—C11	1.387 (2)
C2—C3	1.383 (2)	C10—H10	0.95
C3—C4	1.375 (2)	C11—C12	1.391 (2)
C3—H3	0.95	C11—H11	0.95
C4—C5	1.379 (2)	C12—H12	0.95
C5—C6	1.372 (2)
C1—O1—H1	113.9 (16)	C5—C6—N3	116.37 (13)
O3—N1—O2	123.45 (14)	C1—C6—N3	120.28 (13)
O3—N1—C2	118.32 (13)	C13—N4—H4A	120.1 (14)
O2—N1—C2	118.22 (13)	C13—N4—H4B	116.6 (13)
O5—N2—O4	124.21 (14)	H4A—N4—H4B	123.2 (19)
O5—N2—C4	117.97 (13)	C8—C7—C12	119.32 (15)
O4—N2—C4	117.82 (13)	C8—C7—C13	117.10 (14)
O6—N3—O7	124.09 (14)	C12—C7—C13	123.59 (15)
O6—N3—C6	116.70 (12)	C9—C8—C7	120.77 (15)
O7—N3—C6	119.21 (12)	C9—C8—H8	119.6
O1—C1—C2	126.91 (14)	C7—C8—H8	119.6
O1—C1—C6	118.25 (14)	C8—C9—C10	119.85 (16)
C2—C1—C6	114.82 (13)	C8—C9—H9	120.1
C3—C2—C1	122.92 (14)	C10—C9—H9	120.1
C3—C2—N1	116.43 (14)	C11—C10—C9	120.01 (15)
C1—C2—N1	120.64 (14)	C11—C10—H10	120.0
C4—C3—C2	118.41 (14)	C9—C10—H10	120.0
C4—C3—H3	120.8	C10—C11—C12	120.18 (16)
C2—C3—H3	120.8	C10—C11—H11	119.9
C3—C4—C5	122.10 (14)	C12—C11—H11	119.9
C3—C4—N2	119.57 (14)	C11—C12—C7	119.87 (16)
C5—C4—N2	118.32 (14)	C11—C12—H12	120.1
C6—C5—C4	118.48 (14)	C7—C12—H12	120.1
C6—C5—H5	120.8	O8—C13—N4	121.60 (15)
C4—C5—H5	120.8	O8—C13—C7	119.32 (14)
C5—C6—C1	123.24 (14)	N4—C13—C7	119.08 (14)
O1—C1—C2—C3	178.66 (14)	O1—C1—C6—C5	−177.29 (14)
C6—C1—C2—C3	0.3 (2)	C2—C1—C6—C5	1.2 (2)
O1—C1—C2—N1	0.1 (2)	O1—C1—C6—N3	−1.1 (2)
C6—C1—C2—N1	−178.30 (13)	C2—C1—C6—N3	177.36 (13)
O3—N1—C2—C3	9.0 (2)	O6—N3—C6—C5	28.3 (2)
O2—N1—C2—C3	−169.57 (13)	O7—N3—C6—C5	−151.32 (14)
O3—N1—C2—C1	−172.29 (14)	O6—N3—C6—C1	−148.15 (14)
O2—N1—C2—C1	9.1 (2)	O7—N3—C6—C1	32.3 (2)
C1—C2—C3—C4	−1.2 (2)	C12—C7—C8—C9	0.2 (2)
N1—C2—C3—C4	177.46 (13)	C13—C7—C8—C9	−179.82 (14)
C2—C3—C4—C5	0.6 (2)	C7—C8—C9—C10	0.3 (2)
C2—C3—C4—N2	−178.32 (13)	C8—C9—C10—C11	−0.4 (2)
O5—N2—C4—C3	−179.43 (14)	C9—C10—C11—C12	0.1 (2)
O4—N2—C4—C3	0.8 (2)	C10—C11—C12—C7	0.4 (2)
O5—N2—C4—C5	1.6 (2)	C8—C7—C12—C11	−0.5 (2)
O4—N2—C4—C5	−178.23 (14)	C13—C7—C12—C11	179.50 (15)
C3—C4—C5—C6	0.8 (2)	C8—C7—C13—O8	3.8 (2)
N2—C4—C5—C6	179.76 (13)	C12—C7—C13—O8	−176.21 (15)
C4—C5—C6—C1	−1.8 (2)	C8—C7—C13—N4	−175.26 (14)
C4—C5—C6—N3	−178.05 (13)	C12—C7—C13—N4	4.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.94 (3)	1.92 (3)	2.6473 (16)	132 (2)
O1—H1···O8	0.94 (3)	1.85 (3)	2.5603 (16)	130 (2)
N4—H4A···O7i	0.87 (2)	2.33 (2)	3.120 (2)	150 (2)
N4—H4B···O8i	0.90 (2)	2.08 (2)	2.9702 (19)	167 (2)
C5—H5···O6ii	0.95	2.39	3.257 (2)	152
C9—H9···O4iii	0.95	2.50	3.185 (2)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.94 (3)	1.92 (3)	2.6473 (16)	132 (2)
O1—H1⋯O8	0.94 (3)	1.85 (3)	2.5603 (16)	130 (2)
N4—H4A⋯O7i	0.87 (2)	2.33 (2)	3.120 (2)	150 (2)
N4—H4B⋯O8i	0.90 (2)	2.08 (2)	2.9702 (19)	167 (2)
C5—H5⋯O6ii	0.95	2.39	3.257 (2)	152
C9—H9⋯O4iii	0.95	2.50	3.185 (2)	129

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