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In the title compound, C14H11N3O4, the dihedral angle between the two benzene rings is 8.1 (2)°. The mol­ecules are linked into chains through N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028024/bi2195sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028024/bi2195Isup2.hkl
Contains datablock I

CCDC reference: 654952

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.042
  • wR factor = 0.124
  • Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

This structure report is an extension of our work on the characterization of hydrazide derivatives (Qiu, Fang et al., 2006; Qiu, Luo et al., 2006).

In the title compound (Fig. 1), the dihedral angle between the two benzene rings is 8.1 (2) °. The molecules are linked through intermolecular N—H···O hydrogen bonds into chains running along the a-axis (Fig. 2).

Related literature top

This structure report is an extension of our work on the characterization of hydrazide derivatives (Qiu, Fang et al., 2006; Qiu, Luo et al., 2006).

Experimental top

The title compound was synthesized by reaction of equivalent amounts of benzohydrazide (0.14 g, 1 mmol) and 2-nitrobenzoyl chloride (0.19 g, 1 mmol) in ethyl acetate (25 ml) for 3 h at 373–393 K. Single crystals for X-ray diffraction analysis were obtained by evaporation of an ethyl acetate solution.

Refinement top

Atoms H7 and H8 were located in a difference Fourier map and refined isotropically without restraint. The refined N—H distances are 0.91 (2) and 0.90 (2) Å. All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).

Structure description top

This structure report is an extension of our work on the characterization of hydrazide derivatives (Qiu, Fang et al., 2006; Qiu, Luo et al., 2006).

In the title compound (Fig. 1), the dihedral angle between the two benzene rings is 8.1 (2) °. The molecules are linked through intermolecular N—H···O hydrogen bonds into chains running along the a-axis (Fig. 2).

This structure report is an extension of our work on the characterization of hydrazide derivatives (Qiu, Fang et al., 2006; Qiu, Luo et al., 2006).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing displacement ellipsoids at 30% probability for non-H atoms.
[Figure 2] Fig. 2. View along the direction of propagation of the hydrogen-bonded chains (the a-axis).
N'-(2-Nitrobenzoyl)benzohydrazide top
Crystal data top
C14H11N3O4F(000) = 592
Mr = 285.26Dx = 1.385 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2796 reflections
a = 8.2363 (16) Åθ = 4.2–25°
b = 12.834 (3) ŵ = 0.10 mm1
c = 12.955 (3) ÅT = 298 K
β = 92.78 (3)°Block, colourless
V = 1367.8 (5) Å30.16 × 0.08 × 0.06 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
3313 independent reflections
Radiation source: fine-focus sealed tube1747 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω scansθmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.988, Tmax = 0.991k = 1717
10170 measured reflectionsl = 1717
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.124 w = 1/[σ2(Fo2) + (0.0672P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max < 0.001
3313 reflectionsΔρmax = 0.17 e Å3
199 parametersΔρmin = 0.15 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0064 (15)
Crystal data top
C14H11N3O4V = 1367.8 (5) Å3
Mr = 285.26Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.2363 (16) ŵ = 0.10 mm1
b = 12.834 (3) ÅT = 298 K
c = 12.955 (3) Å0.16 × 0.08 × 0.06 mm
β = 92.78 (3)°
Data collection top
Bruker SMART APEX CCD
diffractometer
3313 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1747 reflections with I > 2σ(I)
Tmin = 0.988, Tmax = 0.991Rint = 0.032
10170 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 0.95Δρmax = 0.17 e Å3
3313 reflectionsΔρmin = 0.15 e Å3
199 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.07092 (13)0.01088 (8)0.37340 (8)0.0562 (3)
C70.19938 (19)0.05391 (11)0.39718 (12)0.0458 (4)
O20.43196 (14)0.15833 (9)0.48726 (9)0.0617 (3)
C20.28541 (18)0.23966 (11)0.34355 (11)0.0467 (4)
N20.24453 (17)0.04930 (10)0.54726 (10)0.0557 (4)
C80.31783 (18)0.14319 (12)0.54234 (11)0.0480 (4)
C10.27361 (17)0.13295 (11)0.32778 (11)0.0441 (4)
N30.21728 (19)0.28640 (11)0.43411 (11)0.0644 (4)
O40.13109 (17)0.23342 (11)0.48638 (10)0.0794 (4)
N10.29262 (18)0.02943 (11)0.48098 (11)0.0567 (4)
C50.4118 (2)0.15825 (13)0.16931 (13)0.0609 (5)
H50.45530.13030.11050.073*
C60.3380 (2)0.09398 (12)0.23843 (12)0.0566 (4)
H60.33110.02290.22490.068*
C30.3582 (2)0.30420 (12)0.27425 (13)0.0548 (4)
H30.36430.37550.28670.066*
C90.25532 (18)0.22508 (12)0.61152 (12)0.0516 (4)
C40.4212 (2)0.26365 (13)0.18751 (13)0.0577 (4)
H40.47030.30720.14080.069*
C100.1773 (2)0.20236 (14)0.70013 (14)0.0636 (5)
H100.16000.13330.71850.076*
O30.2459 (3)0.37735 (12)0.45241 (13)0.1253 (7)
C140.2827 (2)0.32818 (14)0.58496 (16)0.0727 (5)
H140.33830.34420.52620.087*
C110.1241 (2)0.2825 (2)0.76252 (16)0.0848 (7)
H110.07160.26730.82260.102*
C120.1499 (3)0.3842 (2)0.7347 (2)0.1023 (9)
H120.11470.43800.77620.123*
C130.2263 (3)0.40685 (16)0.6470 (2)0.0994 (8)
H130.24090.47610.62830.119*
H80.146 (2)0.0389 (12)0.5726 (12)0.060 (5)*
H70.382 (2)0.0660 (15)0.5020 (14)0.078 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0534 (7)0.0529 (7)0.0630 (7)0.0075 (5)0.0112 (6)0.0014 (5)
C70.0465 (9)0.0409 (8)0.0512 (9)0.0023 (7)0.0150 (8)0.0010 (7)
O20.0573 (7)0.0653 (8)0.0640 (7)0.0040 (5)0.0176 (6)0.0002 (6)
C20.0517 (9)0.0440 (8)0.0453 (8)0.0049 (7)0.0115 (7)0.0024 (7)
N20.0523 (8)0.0541 (8)0.0623 (9)0.0022 (7)0.0200 (7)0.0199 (6)
C80.0463 (9)0.0522 (10)0.0456 (9)0.0055 (7)0.0034 (8)0.0038 (7)
C10.0447 (9)0.0427 (8)0.0456 (8)0.0022 (6)0.0100 (7)0.0042 (6)
N30.0843 (11)0.0494 (9)0.0616 (9)0.0037 (7)0.0239 (8)0.0058 (7)
O40.0975 (10)0.0758 (9)0.0687 (8)0.0047 (7)0.0438 (8)0.0031 (6)
N10.0536 (9)0.0549 (8)0.0621 (9)0.0107 (7)0.0090 (8)0.0197 (7)
C50.0698 (12)0.0679 (11)0.0465 (9)0.0038 (9)0.0190 (9)0.0021 (8)
C60.0681 (11)0.0478 (9)0.0554 (10)0.0008 (7)0.0188 (9)0.0010 (7)
C30.0613 (11)0.0427 (8)0.0610 (10)0.0036 (7)0.0087 (9)0.0114 (7)
C90.0488 (10)0.0524 (10)0.0529 (10)0.0066 (7)0.0046 (8)0.0112 (7)
C40.0624 (11)0.0601 (10)0.0519 (10)0.0005 (8)0.0151 (8)0.0169 (8)
C100.0613 (11)0.0712 (11)0.0587 (11)0.0040 (9)0.0060 (9)0.0213 (9)
O30.1998 (19)0.0605 (9)0.1222 (13)0.0202 (10)0.0747 (13)0.0333 (9)
C140.0831 (14)0.0571 (11)0.0767 (13)0.0068 (9)0.0091 (11)0.0064 (9)
C110.0757 (14)0.1096 (19)0.0690 (13)0.0188 (12)0.0030 (11)0.0430 (12)
C120.1058 (19)0.0932 (19)0.105 (2)0.0409 (14)0.0203 (16)0.0565 (16)
C130.123 (2)0.0572 (12)0.114 (2)0.0236 (13)0.0272 (17)0.0266 (13)
Geometric parameters (Å, º) top
O1—C71.2197 (18)C5—H50.930
C7—N11.336 (2)C6—H60.930
C7—C11.5050 (19)C3—C41.364 (2)
O2—C81.2230 (18)C3—H30.930
C2—C31.380 (2)C9—C101.374 (2)
C2—C11.387 (2)C9—C141.388 (2)
C2—N31.454 (2)C4—H40.930
N2—C81.351 (2)C10—C111.392 (2)
N2—N11.3958 (17)C10—H100.930
N2—H80.90 (2)C14—C131.385 (3)
C8—C91.489 (2)C14—H140.930
C1—C61.389 (2)C11—C121.374 (4)
N3—O31.2119 (19)C11—H110.930
N3—O41.2131 (18)C12—C131.356 (4)
N1—H70.91 (2)C12—H120.930
C5—C41.375 (2)C13—H130.930
C5—C61.380 (2)
O1—C7—N1123.78 (14)C1—C6—H6119.2
O1—C7—C1121.80 (15)C4—C3—C2120.12 (15)
N1—C7—C1114.19 (13)C4—C3—H3119.9
C3—C2—C1121.76 (14)C2—C3—H3119.9
C3—C2—N3118.30 (14)C10—C9—C14119.84 (15)
C1—C2—N3119.93 (13)C10—C9—C8122.86 (15)
C8—N2—N1118.42 (13)C14—C9—C8117.27 (15)
C8—N2—H8124.3 (10)C3—C4—C5119.76 (14)
N1—N2—H8113.9 (11)C3—C4—H4120.1
O2—C8—N2121.83 (14)C5—C4—H4120.1
O2—C8—C9122.48 (15)C9—C10—C11120.12 (19)
N2—C8—C9115.64 (13)C9—C10—H10119.9
C2—C1—C6116.82 (13)C11—C10—H10119.9
C2—C1—C7127.23 (13)C13—C14—C9119.2 (2)
C6—C1—C7115.95 (13)C13—C14—H14120.4
O3—N3—O4122.98 (15)C9—C14—H14120.4
O3—N3—C2118.43 (15)C12—C11—C10119.5 (2)
O4—N3—C2118.57 (14)C12—C11—H11120.2
C7—N1—N2120.06 (14)C10—C11—H11120.2
C7—N1—H7123.4 (12)C13—C12—C11120.48 (19)
N2—N1—H7116.2 (12)C13—C12—H12119.8
C4—C5—C6119.98 (15)C11—C12—H12119.8
C4—C5—H5120.0C12—C13—C14120.8 (2)
C6—C5—H5120.0C12—C13—H13119.6
C5—C6—C1121.55 (15)C14—C13—H13119.6
C5—C6—H6119.2
N1—N2—C8—O25.4 (2)C2—C1—C6—C50.8 (2)
N1—N2—C8—C9177.18 (13)C7—C1—C6—C5178.91 (15)
C3—C2—C1—C60.3 (2)C1—C2—C3—C40.1 (3)
N3—C2—C1—C6178.52 (15)N3—C2—C3—C4178.94 (15)
C3—C2—C1—C7179.32 (15)O2—C8—C9—C10153.43 (17)
N3—C2—C1—C71.9 (2)N2—C8—C9—C1024.0 (2)
O1—C7—C1—C2108.89 (18)O2—C8—C9—C1424.7 (2)
N1—C7—C1—C276.56 (19)N2—C8—C9—C14157.83 (15)
O1—C7—C1—C671.49 (19)C2—C3—C4—C50.1 (3)
N1—C7—C1—C6103.06 (16)C6—C5—C4—C30.4 (3)
C3—C2—N3—O39.7 (3)C14—C9—C10—C110.8 (3)
C1—C2—N3—O3171.39 (17)C8—C9—C10—C11178.90 (15)
C3—C2—N3—O4168.42 (15)C10—C9—C14—C131.9 (3)
C1—C2—N3—O410.5 (2)C8—C9—C14—C13179.82 (16)
O1—C7—N1—N20.1 (2)C9—C10—C11—C120.2 (3)
C1—C7—N1—N2174.57 (13)C10—C11—C12—C130.1 (3)
C8—N2—N1—C7103.18 (17)C11—C12—C13—C141.3 (4)
C4—C5—C6—C10.8 (3)C9—C14—C13—C122.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H8···O1i0.90 (2)1.99 (2)2.8825 (18)178.0 (15)
N1—H7···O2ii0.91 (2)1.93 (2)2.8216 (19)165.8 (17)
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC14H11N3O4
Mr285.26
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)8.2363 (16), 12.834 (3), 12.955 (3)
β (°) 92.78 (3)
V3)1367.8 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.16 × 0.08 × 0.06
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.988, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
10170, 3313, 1747
Rint0.032
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.124, 0.95
No. of reflections3313
No. of parameters199
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.17, 0.15

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H8···O1i0.90 (2)1.99 (2)2.8825 (18)178.0 (15)
N1—H7···O2ii0.91 (2)1.93 (2)2.8216 (19)165.8 (17)
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z+1.
 

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