1-Benzoyl-4-(2-nitro-phen-yl)semicarbazide.

The title compound, C(14)H(12)N(4)O(4), was prepared by the reaction of 2-nitro-phenyl isocyanate with benzoyl-hydrazine. The dihedral angle between the rings is 71.49 (6)) Å. The mol-ecular conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond, generating an S(6) ring. The crystal packing shows N-H⋯O hydrogen bonds.

Related literature

For the bioactivity of urea derivatives, see: Yip et al. (1986 ▶); Liu et al. (2005 ▶).

Experimental

Crystal data

C14H12N4O4

M = 300.28

Monoclinic,

a = 4.655 (2) Å

b = 15.020 (7) Å

c = 10.005 (5) Å

β = 97.954 (7)°

V = 692.9 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 113 K

0.20 × 0.16 × 0.12 mm

Data collection

Rigaku Saturn 724 CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.979, T max = 0.987

5816 measured reflections

1652 independent reflections

1383 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.059

S = 0.96

1652 reflections

212 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 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: XP (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810013048/bt5244sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013048/bt5244Isup2.hkl

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

C14H12N4O4	F(000) = 312
Mr = 300.28	Dx = 1.439 Mg m−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 2582 reflections
a = 4.655 (2) Å	θ = 1.4–27.9°
b = 15.020 (7) Å	µ = 0.11 mm−1
c = 10.005 (5) Å	T = 113 K
β = 97.954 (7)°	Prism, colorless
V = 692.9 (5) Å3	0.20 × 0.16 × 0.12 mm
Z = 2

Rigaku Saturn 724 CCD area-detector diffractometer	1652 independent reflections
Radiation source: fine-focus sealed tube	1383 reflections with I > 2σ(I)
graphite	Rint = 0.033
Detector resolution: 14.68 pixels mm-1	θmax = 27.9°, θmin = 1.4°
ω and φ scans	h = −4→6
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −16→19
Tmin = 0.979, Tmax = 0.987	l = −13→12
5816 measured reflections

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)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.059	w = 1/[σ2(Fo2) + (0.0305P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max = 0.007
1652 reflections	Δρmax = 0.17 e Å−3
212 parameters	Δρmin = −0.16 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.044 (4)

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 > 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	0.4760 (3)	−0.01804 (9)	0.99297 (16)	0.0318 (4)
O2	0.4185 (3)	0.12193 (9)	1.02923 (16)	0.0305 (4)
O3	1.1178 (3)	0.32395 (8)	0.92954 (15)	0.0224 (3)
O4	0.8286 (3)	0.48594 (9)	0.76324 (14)	0.0256 (3)
N1	0.6951 (4)	0.24346 (11)	0.90518 (17)	0.0191 (4)
H1	0.539 (5)	0.2410 (13)	0.936 (2)	0.021 (6)*
N2	0.6976 (4)	0.38858 (10)	0.97176 (17)	0.0172 (3)
H2A	0.523 (5)	0.3870 (12)	0.958 (2)	0.014 (5)*
N3	0.8310 (3)	0.47099 (10)	0.98749 (17)	0.0183 (3)
H3A	0.853 (5)	0.4899 (15)	1.073 (2)	0.031 (6)*
N4	0.5259 (3)	0.06040 (10)	0.97133 (17)	0.0220 (4)
C1	0.7987 (3)	0.16832 (12)	0.8453 (2)	0.0169 (4)
C2	0.7208 (4)	0.08059 (13)	0.8735 (2)	0.0186 (4)
C3	0.8283 (4)	0.00766 (13)	0.8095 (2)	0.0238 (5)
H3	0.7730	−0.0509	0.8310	0.029*
C4	1.0138 (4)	0.02023 (13)	0.7156 (2)	0.0244 (5)
H4	1.0907	−0.0293	0.6734	0.029*
C5	1.0872 (4)	0.10670 (13)	0.6832 (2)	0.0228 (4)
H5	1.2108	0.1160	0.6165	0.027*
C6	0.9833 (4)	0.17889 (12)	0.7465 (2)	0.0181 (4)
H6	1.0377	0.2372	0.7229	0.022*
C7	0.8559 (4)	0.31947 (12)	0.93330 (19)	0.0165 (4)
C8	0.9025 (4)	0.51379 (12)	0.8784 (2)	0.0189 (4)
C9	1.0848 (4)	0.59575 (12)	0.9075 (2)	0.0202 (4)
C10	1.2623 (4)	0.60775 (13)	1.0298 (2)	0.0228 (4)
H10	1.2638	0.5648	1.0996	0.027*
C11	1.4379 (4)	0.68291 (13)	1.0494 (2)	0.0297 (5)
H11	1.5598	0.6910	1.1328	0.036*
C12	1.4367 (5)	0.74538 (13)	0.9493 (3)	0.0337 (5)
H12	1.5576	0.7964	0.9636	0.040*
C13	1.2588 (5)	0.73400 (15)	0.8273 (3)	0.0404 (6)
H13	1.2560	0.7776	0.7583	0.048*
C14	1.0851 (5)	0.65894 (14)	0.8064 (2)	0.0339 (5)
H14	0.9656	0.6507	0.7224	0.041*

	U11	U22	U33	U12	U13	U23
O1	0.0371 (9)	0.0231 (8)	0.0370 (10)	−0.0064 (6)	0.0116 (7)	0.0067 (7)
O2	0.0351 (8)	0.0255 (8)	0.0349 (10)	0.0007 (7)	0.0189 (7)	0.0013 (7)
O3	0.0137 (6)	0.0229 (7)	0.0310 (8)	−0.0021 (5)	0.0050 (5)	−0.0033 (6)
O4	0.0360 (8)	0.0254 (7)	0.0149 (8)	−0.0060 (6)	0.0018 (6)	−0.0025 (6)
N1	0.0144 (8)	0.0190 (8)	0.0256 (10)	−0.0022 (6)	0.0089 (7)	−0.0017 (7)
N2	0.0137 (8)	0.0160 (8)	0.0223 (9)	−0.0024 (6)	0.0036 (6)	−0.0027 (7)
N3	0.0224 (8)	0.0174 (8)	0.0156 (9)	−0.0034 (6)	0.0045 (6)	−0.0038 (7)
N4	0.0203 (8)	0.0228 (9)	0.0224 (10)	−0.0023 (7)	0.0007 (7)	0.0040 (7)
C1	0.0114 (9)	0.0190 (9)	0.0196 (11)	−0.0001 (7)	−0.0002 (7)	−0.0003 (8)
C2	0.0158 (9)	0.0210 (9)	0.0185 (10)	−0.0010 (7)	0.0011 (7)	0.0002 (8)
C3	0.0229 (10)	0.0180 (9)	0.0295 (12)	0.0005 (8)	0.0002 (8)	−0.0009 (8)
C4	0.0233 (10)	0.0219 (10)	0.0281 (12)	0.0034 (8)	0.0038 (8)	−0.0063 (9)
C5	0.0191 (10)	0.0281 (11)	0.0217 (11)	−0.0005 (8)	0.0043 (8)	−0.0013 (9)
C6	0.0150 (8)	0.0198 (10)	0.0199 (11)	−0.0006 (7)	0.0033 (7)	0.0012 (8)
C7	0.0166 (9)	0.0201 (9)	0.0130 (10)	−0.0006 (7)	0.0024 (7)	0.0018 (7)
C8	0.0205 (10)	0.0182 (9)	0.0181 (10)	0.0011 (7)	0.0033 (7)	−0.0001 (8)
C9	0.0241 (10)	0.0174 (9)	0.0201 (10)	−0.0005 (8)	0.0066 (8)	−0.0016 (8)
C10	0.0245 (10)	0.0216 (10)	0.0228 (11)	−0.0028 (8)	0.0055 (8)	−0.0010 (8)
C11	0.0263 (11)	0.0307 (11)	0.0324 (13)	−0.0058 (9)	0.0049 (9)	−0.0086 (10)
C12	0.0414 (13)	0.0227 (11)	0.0395 (15)	−0.0104 (9)	0.0148 (10)	−0.0086 (10)
C13	0.0603 (16)	0.0267 (12)	0.0353 (16)	−0.0126 (11)	0.0107 (12)	0.0065 (10)
C14	0.0503 (13)	0.0265 (11)	0.0238 (13)	−0.0079 (10)	0.0012 (10)	0.0028 (9)

O1—N4	1.226 (2)	C4—C5	1.393 (3)
O2—N4	1.233 (2)	C4—H4	0.9500
O3—C7	1.227 (2)	C5—C6	1.377 (3)
O4—C8	1.229 (2)	C5—H5	0.9500
N1—C7	1.373 (2)	C6—H6	0.9500
N1—C1	1.395 (2)	C8—C9	1.500 (3)
N1—H1	0.83 (2)	C9—C14	1.387 (3)
N2—C7	1.359 (2)	C9—C10	1.390 (3)
N2—N3	1.384 (2)	C10—C11	1.392 (3)
N2—H2A	0.80 (2)	C10—H10	0.9500
N3—C8	1.348 (3)	C11—C12	1.371 (3)
N3—H3A	0.90 (2)	C11—H11	0.9500
N4—C2	1.456 (3)	C12—C13	1.388 (3)
C1—C6	1.405 (3)	C12—H12	0.9500
C1—C2	1.406 (3)	C13—C14	1.386 (3)
C2—C3	1.396 (3)	C13—H13	0.9500
C3—C4	1.374 (3)	C14—H14	0.9500
C3—H3	0.9500
C7—N1—C1	123.34 (16)	C5—C6—C1	121.51 (18)
C7—N1—H1	116.3 (14)	C5—C6—H6	119.2
C1—N1—H1	119.8 (14)	C1—C6—H6	119.2
C7—N2—N3	117.57 (16)	O3—C7—N2	123.16 (16)
C7—N2—H2A	120.0 (14)	O3—C7—N1	123.73 (17)
N3—N2—H2A	118.2 (13)	N2—C7—N1	113.05 (15)
C8—N3—N2	119.45 (16)	O4—C8—N3	121.89 (17)
C8—N3—H3A	128.0 (15)	O4—C8—C9	122.59 (17)
N2—N3—H3A	112.5 (15)	N3—C8—C9	115.49 (17)
O1—N4—O2	122.58 (17)	C14—C9—C10	119.50 (18)
O1—N4—C2	118.03 (17)	C14—C9—C8	118.53 (18)
O2—N4—C2	119.39 (15)	C10—C9—C8	121.90 (17)
N1—C1—C6	119.49 (16)	C9—C10—C11	119.69 (19)
N1—C1—C2	123.91 (16)	C9—C10—H10	120.2
C6—C1—C2	116.54 (16)	C11—C10—H10	120.2
C3—C2—C1	121.65 (18)	C12—C11—C10	120.6 (2)
C3—C2—N4	116.19 (16)	C12—C11—H11	119.7
C1—C2—N4	122.16 (16)	C10—C11—H11	119.7
C4—C3—C2	120.32 (19)	C11—C12—C13	120.0 (2)
C4—C3—H3	119.8	C11—C12—H12	120.0
C2—C3—H3	119.8	C13—C12—H12	120.0
C3—C4—C5	119.01 (19)	C14—C13—C12	119.8 (2)
C3—C4—H4	120.5	C14—C13—H13	120.1
C5—C4—H4	120.5	C12—C13—H13	120.1
C6—C5—C4	120.9 (2)	C13—C14—C9	120.4 (2)
C6—C5—H5	119.5	C13—C14—H14	119.8
C4—C5—H5	119.5	C9—C14—H14	119.8
C7—N2—N3—C8	67.4 (2)	N3—N2—C7—O3	10.0 (3)
C7—N1—C1—C6	−35.8 (3)	N3—N2—C7—N1	−172.79 (16)
C7—N1—C1—C2	146.84 (18)	C1—N1—C7—O3	−12.5 (3)
N1—C1—C2—C3	179.25 (18)	C1—N1—C7—N2	170.32 (17)
C6—C1—C2—C3	1.8 (2)	N2—N3—C8—O4	7.0 (3)
N1—C1—C2—N4	−1.2 (2)	N2—N3—C8—C9	−171.28 (16)
C6—C1—C2—N4	−178.62 (16)	O4—C8—C9—C14	23.4 (3)
O1—N4—C2—C3	1.8 (2)	N3—C8—C9—C14	−158.26 (18)
O2—N4—C2—C3	−178.46 (17)	O4—C8—C9—C10	−153.41 (19)
O1—N4—C2—C1	−177.80 (17)	N3—C8—C9—C10	24.9 (2)
O2—N4—C2—C1	2.0 (2)	C14—C9—C10—C11	0.0 (3)
C1—C2—C3—C4	−0.4 (3)	C8—C9—C10—C11	176.84 (17)
N4—C2—C3—C4	180.00 (16)	C9—C10—C11—C12	0.2 (3)
C2—C3—C4—C5	−1.4 (3)	C10—C11—C12—C13	0.1 (3)
C3—C4—C5—C6	1.8 (3)	C11—C12—C13—C14	−0.7 (4)
C4—C5—C6—C1	−0.4 (3)	C12—C13—C14—C9	1.0 (4)
N1—C1—C6—C5	−178.97 (17)	C10—C9—C14—C13	−0.6 (3)
C2—C1—C6—C5	−1.4 (3)	C8—C9—C14—C13	−177.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3i	0.80 (2)	2.10 (2)	2.844 (2)	154.8 (18)
N3—H3A···O4ii	0.90 (2)	1.95 (2)	2.835 (2)	167 (2)
N1—H1···O2	0.83 (2)	2.13 (2)	2.640 (2)	119.8 (17)
N1—H1···O3i	0.83 (2)	2.32 (2)	2.987 (2)	138.7 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3i	0.80 (2)	2.10 (2)	2.844 (2)	154.8 (18)
N3—H3A⋯O4ii	0.90 (2)	1.95 (2)	2.835 (2)	167 (2)
N1—H1⋯O2	0.83 (2)	2.13 (2)	2.640 (2)	119.8 (17)
N1—H1⋯O3i	0.83 (2)	2.32 (2)	2.987 (2)	138.7 (19)

Symmetry codes: (i) ; (ii) .