Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028024/bi2195sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028024/bi2195Isup2.hkl |
CCDC reference: 654952
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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).
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.
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).
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).
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.
C14H11N3O4 | F(000) = 592 |
Mr = 285.26 | Dx = 1.385 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2796 reflections |
a = 8.2363 (16) Å | θ = 4.2–25° |
b = 12.834 (3) Å | µ = 0.10 mm−1 |
c = 12.955 (3) Å | T = 298 K |
β = 92.78 (3)° | Block, colourless |
V = 1367.8 (5) Å3 | 0.16 × 0.08 × 0.06 mm |
Z = 4 |
Bruker SMART APEX CCD diffractometer | 3313 independent reflections |
Radiation source: fine-focus sealed tube | 1747 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ω scans | θmax = 28.3°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.988, Tmax = 0.991 | k = −17→17 |
10170 measured reflections | l = −17→17 |
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)] = 0.042 | H 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 reflections | Δρmax = 0.17 e Å−3 |
199 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0064 (15) |
C14H11N3O4 | V = 1367.8 (5) Å3 |
Mr = 285.26 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.2363 (16) Å | µ = 0.10 mm−1 |
b = 12.834 (3) Å | T = 298 K |
c = 12.955 (3) Å | 0.16 × 0.08 × 0.06 mm |
β = 92.78 (3)° |
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 = 0.991 | Rint = 0.032 |
10170 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.124 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | Δρmax = 0.17 e Å−3 |
3313 reflections | Δρmin = −0.15 e Å−3 |
199 parameters |
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 | 0.07092 (13) | −0.01088 (8) | 0.37340 (8) | 0.0562 (3) | |
C7 | 0.19938 (19) | −0.05391 (11) | 0.39718 (12) | 0.0458 (4) | |
O2 | 0.43196 (14) | 0.15833 (9) | 0.48726 (9) | 0.0617 (3) | |
C2 | 0.28541 (18) | −0.23966 (11) | 0.34355 (11) | 0.0467 (4) | |
N2 | 0.24453 (17) | 0.04930 (10) | 0.54726 (10) | 0.0557 (4) | |
C8 | 0.31783 (18) | 0.14319 (12) | 0.54234 (11) | 0.0480 (4) | |
C1 | 0.27361 (17) | −0.13295 (11) | 0.32778 (11) | 0.0441 (4) | |
N3 | 0.21728 (19) | −0.28640 (11) | 0.43411 (11) | 0.0644 (4) | |
O4 | 0.13109 (17) | −0.23342 (11) | 0.48638 (10) | 0.0794 (4) | |
N1 | 0.29262 (18) | −0.02943 (11) | 0.48098 (11) | 0.0567 (4) | |
C5 | 0.4118 (2) | −0.15825 (13) | 0.16931 (13) | 0.0609 (5) | |
H5 | 0.4553 | −0.1303 | 0.1105 | 0.073* | |
C6 | 0.3380 (2) | −0.09398 (12) | 0.23843 (12) | 0.0566 (4) | |
H6 | 0.3311 | −0.0229 | 0.2249 | 0.068* | |
C3 | 0.3582 (2) | −0.30420 (12) | 0.27425 (13) | 0.0548 (4) | |
H3 | 0.3643 | −0.3755 | 0.2867 | 0.066* | |
C9 | 0.25532 (18) | 0.22508 (12) | 0.61152 (12) | 0.0516 (4) | |
C4 | 0.4212 (2) | −0.26365 (13) | 0.18751 (13) | 0.0577 (4) | |
H4 | 0.4703 | −0.3072 | 0.1408 | 0.069* | |
C10 | 0.1773 (2) | 0.20236 (14) | 0.70013 (14) | 0.0636 (5) | |
H10 | 0.1600 | 0.1333 | 0.7185 | 0.076* | |
O3 | 0.2459 (3) | −0.37735 (12) | 0.45241 (13) | 0.1253 (7) | |
C14 | 0.2827 (2) | 0.32818 (14) | 0.58496 (16) | 0.0727 (5) | |
H14 | 0.3383 | 0.3442 | 0.5262 | 0.087* | |
C11 | 0.1241 (2) | 0.2825 (2) | 0.76252 (16) | 0.0848 (7) | |
H11 | 0.0716 | 0.2673 | 0.8226 | 0.102* | |
C12 | 0.1499 (3) | 0.3842 (2) | 0.7347 (2) | 0.1023 (9) | |
H12 | 0.1147 | 0.4380 | 0.7762 | 0.123* | |
C13 | 0.2263 (3) | 0.40685 (16) | 0.6470 (2) | 0.0994 (8) | |
H13 | 0.2409 | 0.4761 | 0.6283 | 0.119* | |
H8 | 0.146 (2) | 0.0389 (12) | 0.5726 (12) | 0.060 (5)* | |
H7 | 0.382 (2) | −0.0660 (15) | 0.5020 (14) | 0.078 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0534 (7) | 0.0529 (7) | 0.0630 (7) | 0.0075 (5) | 0.0112 (6) | 0.0014 (5) |
C7 | 0.0465 (9) | 0.0409 (8) | 0.0512 (9) | −0.0023 (7) | 0.0150 (8) | −0.0010 (7) |
O2 | 0.0573 (7) | 0.0653 (8) | 0.0640 (7) | 0.0040 (5) | 0.0176 (6) | −0.0002 (6) |
C2 | 0.0517 (9) | 0.0440 (8) | 0.0453 (8) | −0.0049 (7) | 0.0115 (7) | −0.0024 (7) |
N2 | 0.0523 (8) | 0.0541 (8) | 0.0623 (9) | 0.0022 (7) | 0.0200 (7) | −0.0199 (6) |
C8 | 0.0463 (9) | 0.0522 (10) | 0.0456 (9) | 0.0055 (7) | 0.0034 (8) | −0.0038 (7) |
C1 | 0.0447 (9) | 0.0427 (8) | 0.0456 (8) | −0.0022 (6) | 0.0100 (7) | −0.0042 (6) |
N3 | 0.0843 (11) | 0.0494 (9) | 0.0616 (9) | −0.0037 (7) | 0.0239 (8) | 0.0058 (7) |
O4 | 0.0975 (10) | 0.0758 (9) | 0.0687 (8) | −0.0047 (7) | 0.0438 (8) | 0.0031 (6) |
N1 | 0.0536 (9) | 0.0549 (8) | 0.0621 (9) | 0.0107 (7) | 0.0090 (8) | −0.0197 (7) |
C5 | 0.0698 (12) | 0.0679 (11) | 0.0465 (9) | −0.0038 (9) | 0.0190 (9) | −0.0021 (8) |
C6 | 0.0681 (11) | 0.0478 (9) | 0.0554 (10) | −0.0008 (7) | 0.0188 (9) | 0.0010 (7) |
C3 | 0.0613 (11) | 0.0427 (8) | 0.0610 (10) | −0.0036 (7) | 0.0087 (9) | −0.0114 (7) |
C9 | 0.0488 (10) | 0.0524 (10) | 0.0529 (10) | 0.0066 (7) | −0.0046 (8) | −0.0112 (7) |
C4 | 0.0624 (11) | 0.0601 (10) | 0.0519 (10) | −0.0005 (8) | 0.0151 (8) | −0.0169 (8) |
C10 | 0.0613 (11) | 0.0712 (11) | 0.0587 (11) | 0.0040 (9) | 0.0060 (9) | −0.0213 (9) |
O3 | 0.1998 (19) | 0.0605 (9) | 0.1222 (13) | 0.0202 (10) | 0.0747 (13) | 0.0333 (9) |
C14 | 0.0831 (14) | 0.0571 (11) | 0.0767 (13) | 0.0068 (9) | −0.0091 (11) | −0.0064 (9) |
C11 | 0.0757 (14) | 0.1096 (19) | 0.0690 (13) | 0.0188 (12) | 0.0030 (11) | −0.0430 (12) |
C12 | 0.1058 (19) | 0.0932 (19) | 0.105 (2) | 0.0409 (14) | −0.0203 (16) | −0.0565 (16) |
C13 | 0.123 (2) | 0.0572 (12) | 0.114 (2) | 0.0236 (13) | −0.0272 (17) | −0.0266 (13) |
O1—C7 | 1.2197 (18) | C5—H5 | 0.930 |
C7—N1 | 1.336 (2) | C6—H6 | 0.930 |
C7—C1 | 1.5050 (19) | C3—C4 | 1.364 (2) |
O2—C8 | 1.2230 (18) | C3—H3 | 0.930 |
C2—C3 | 1.380 (2) | C9—C10 | 1.374 (2) |
C2—C1 | 1.387 (2) | C9—C14 | 1.388 (2) |
C2—N3 | 1.454 (2) | C4—H4 | 0.930 |
N2—C8 | 1.351 (2) | C10—C11 | 1.392 (2) |
N2—N1 | 1.3958 (17) | C10—H10 | 0.930 |
N2—H8 | 0.90 (2) | C14—C13 | 1.385 (3) |
C8—C9 | 1.489 (2) | C14—H14 | 0.930 |
C1—C6 | 1.389 (2) | C11—C12 | 1.374 (4) |
N3—O3 | 1.2119 (19) | C11—H11 | 0.930 |
N3—O4 | 1.2131 (18) | C12—C13 | 1.356 (4) |
N1—H7 | 0.91 (2) | C12—H12 | 0.930 |
C5—C4 | 1.375 (2) | C13—H13 | 0.930 |
C5—C6 | 1.380 (2) | ||
O1—C7—N1 | 123.78 (14) | C1—C6—H6 | 119.2 |
O1—C7—C1 | 121.80 (15) | C4—C3—C2 | 120.12 (15) |
N1—C7—C1 | 114.19 (13) | C4—C3—H3 | 119.9 |
C3—C2—C1 | 121.76 (14) | C2—C3—H3 | 119.9 |
C3—C2—N3 | 118.30 (14) | C10—C9—C14 | 119.84 (15) |
C1—C2—N3 | 119.93 (13) | C10—C9—C8 | 122.86 (15) |
C8—N2—N1 | 118.42 (13) | C14—C9—C8 | 117.27 (15) |
C8—N2—H8 | 124.3 (10) | C3—C4—C5 | 119.76 (14) |
N1—N2—H8 | 113.9 (11) | C3—C4—H4 | 120.1 |
O2—C8—N2 | 121.83 (14) | C5—C4—H4 | 120.1 |
O2—C8—C9 | 122.48 (15) | C9—C10—C11 | 120.12 (19) |
N2—C8—C9 | 115.64 (13) | C9—C10—H10 | 119.9 |
C2—C1—C6 | 116.82 (13) | C11—C10—H10 | 119.9 |
C2—C1—C7 | 127.23 (13) | C13—C14—C9 | 119.2 (2) |
C6—C1—C7 | 115.95 (13) | C13—C14—H14 | 120.4 |
O3—N3—O4 | 122.98 (15) | C9—C14—H14 | 120.4 |
O3—N3—C2 | 118.43 (15) | C12—C11—C10 | 119.5 (2) |
O4—N3—C2 | 118.57 (14) | C12—C11—H11 | 120.2 |
C7—N1—N2 | 120.06 (14) | C10—C11—H11 | 120.2 |
C7—N1—H7 | 123.4 (12) | C13—C12—C11 | 120.48 (19) |
N2—N1—H7 | 116.2 (12) | C13—C12—H12 | 119.8 |
C4—C5—C6 | 119.98 (15) | C11—C12—H12 | 119.8 |
C4—C5—H5 | 120.0 | C12—C13—C14 | 120.8 (2) |
C6—C5—H5 | 120.0 | C12—C13—H13 | 119.6 |
C5—C6—C1 | 121.55 (15) | C14—C13—H13 | 119.6 |
C5—C6—H6 | 119.2 | ||
N1—N2—C8—O2 | −5.4 (2) | C2—C1—C6—C5 | −0.8 (2) |
N1—N2—C8—C9 | 177.18 (13) | C7—C1—C6—C5 | 178.91 (15) |
C3—C2—C1—C6 | 0.3 (2) | C1—C2—C3—C4 | 0.1 (3) |
N3—C2—C1—C6 | −178.52 (15) | N3—C2—C3—C4 | 178.94 (15) |
C3—C2—C1—C7 | −179.32 (15) | O2—C8—C9—C10 | −153.43 (17) |
N3—C2—C1—C7 | 1.9 (2) | N2—C8—C9—C10 | 24.0 (2) |
O1—C7—C1—C2 | −108.89 (18) | O2—C8—C9—C14 | 24.7 (2) |
N1—C7—C1—C2 | 76.56 (19) | N2—C8—C9—C14 | −157.83 (15) |
O1—C7—C1—C6 | 71.49 (19) | C2—C3—C4—C5 | −0.1 (3) |
N1—C7—C1—C6 | −103.06 (16) | C6—C5—C4—C3 | −0.4 (3) |
C3—C2—N3—O3 | 9.7 (3) | C14—C9—C10—C11 | 0.8 (3) |
C1—C2—N3—O3 | −171.39 (17) | C8—C9—C10—C11 | 178.90 (15) |
C3—C2—N3—O4 | −168.42 (15) | C10—C9—C14—C13 | −1.9 (3) |
C1—C2—N3—O4 | 10.5 (2) | C8—C9—C14—C13 | 179.82 (16) |
O1—C7—N1—N2 | 0.1 (2) | C9—C10—C11—C12 | 0.2 (3) |
C1—C7—N1—N2 | 174.57 (13) | C10—C11—C12—C13 | 0.1 (3) |
C8—N2—N1—C7 | −103.18 (17) | C11—C12—C13—C14 | −1.3 (4) |
C4—C5—C6—C1 | 0.8 (3) | C9—C14—C13—C12 | 2.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H8···O1i | 0.90 (2) | 1.99 (2) | 2.8825 (18) | 178.0 (15) |
N1—H7···O2ii | 0.91 (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 formula | C14H11N3O4 |
Mr | 285.26 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 8.2363 (16), 12.834 (3), 12.955 (3) |
β (°) | 92.78 (3) |
V (Å3) | 1367.8 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.16 × 0.08 × 0.06 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.988, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10170, 3313, 1747 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.124, 0.95 |
No. of reflections | 3313 |
No. of parameters | 199 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.15 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H8···O1i | 0.90 (2) | 1.99 (2) | 2.8825 (18) | 178.0 (15) |
N1—H7···O2ii | 0.91 (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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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).