(E)-1-Benzyl­idene-2-(4-nitro­phen­yl)hydrazine

In the title Schiff base, C₁₃H₁₁N₃O₂, the dihedral angle between the two aromatic rings is 12.5 (2)°. The crystal packing in consolidated by inter­molecular N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.035
• wR factor = 0.074
• Data-to-parameter ratio = 7.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         38 Perc.

Alert level C
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.722
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.110
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.54
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.47
           From the CIF: _reflns_number_total               1251
           Count of symmetry unique reflns         1253
           Completeness (_total/calc)             99.84%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

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 (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.

(E)-1-benzylidene-2-(4-nitrophenyl)hydrazone

Crystal data

C13H11N3O2	F(000) = 504
Mr = 241.25	Dx = 1.335 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 514 reflections
a = 6.074 (1) Å	θ = 2.7–23.2°
b = 23.338 (3) Å	µ = 0.09 mm^−1
c = 8.527 (2) Å	T = 298 K
β = 96.84 (3)°	Block, yellow
V = 1200.1 (4) Å^3	0.24 × 0.18 × 0.13 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	1251 independent reflections
Radiation source: fine-focus sealed tube	478 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.110
ω scans	θmax = 26.5°, θmin = 3.0°
Absorption correction: multi-scan SADABS (Bruker, date)	h = −7→7
Tmin = 0.978, Tmax = 0.988	k = −29→29
4788 measured reflections	l = −10→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 0.72	w = 1/[σ^2(Fo^2) + (0.0001P)^2] where P = (Fo^2 + 2Fc^2)/3
1251 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.12 e Å^−3
3 restraints	Δρmin = −0.10 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.9907 (6)	0.53251 (17)	−0.1512 (5)	0.0941 (11)
O2	0.9027 (7)	0.45048 (16)	−0.0585 (4)	0.0997 (12)
N1	0.8784 (7)	0.5028 (2)	−0.0721 (5)	0.0772 (12)
N2	0.1940 (6)	0.60586 (17)	0.2086 (4)	0.0653 (10)
N3	0.1424 (6)	0.66184 (16)	0.1780 (4)	0.0656 (10)
C1	0.7028 (7)	0.5304 (2)	0.0019 (6)	0.0591 (12)
C2	0.6639 (7)	0.5879 (2)	−0.0224 (5)	0.0660 (14)
H2	0.7512	0.6092	−0.0835	0.079*
C3	0.4946 (7)	0.61357 (19)	0.0448 (5)	0.0633 (12)
H3	0.4654	0.6524	0.0284	0.076*
C4	0.3661 (7)	0.58125 (19)	0.1382 (6)	0.0574 (12)
C5	0.4080 (7)	0.52335 (19)	0.1615 (5)	0.0630 (13)
H5	0.3227	0.5018	0.2233	0.076*
C6	0.5766 (7)	0.49818 (18)	0.0926 (5)	0.0648 (13)
H6	0.6056	0.4593	0.1073	0.078*
C7	−0.0299 (8)	0.68122 (19)	0.2339 (5)	0.0692 (13)
H7	−0.1103	0.6575	0.2938	0.083*
C8	−0.1001 (8)	0.7406 (2)	0.2037 (5)	0.0675 (13)
C9	−0.2997 (9)	0.7592 (2)	0.2446 (6)	0.0926 (17)
H9	−0.3896	0.7344	0.2940	0.111*
C10	−0.3681 (9)	0.8161 (3)	0.2115 (8)	0.1049 (19)
H10	−0.5019	0.8291	0.2411	0.126*
C11	−0.2410 (13)	0.8515 (3)	0.1374 (8)	0.106 (2)
H11	−0.2880	0.8889	0.1153	0.127*
C12	−0.0447 (12)	0.8335 (2)	0.0943 (7)	0.110 (2)
H12	0.0416	0.8584	0.0421	0.132*
C13	0.0269 (9)	0.7784 (2)	0.1278 (6)	0.0889 (16)
H13	0.1625	0.7664	0.0990	0.107*
H2A	0.113 (6)	0.5824 (15)	0.263 (4)	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.078 (2)	0.119 (3)	0.090 (3)	0.005 (2)	0.028 (2)	−0.016 (2)
O2	0.115 (3)	0.086 (3)	0.099 (3)	0.032 (3)	0.021 (2)	−0.003 (2)
N1	0.072 (3)	0.097 (4)	0.063 (3)	0.006 (3)	0.007 (2)	−0.010 (3)
N2	0.067 (3)	0.059 (3)	0.073 (3)	0.008 (2)	0.018 (2)	0.009 (2)
N3	0.070 (3)	0.060 (3)	0.068 (3)	0.005 (2)	0.011 (2)	0.003 (2)
C1	0.056 (3)	0.065 (3)	0.056 (3)	0.010 (3)	0.007 (2)	0.000 (3)
C2	0.074 (4)	0.062 (3)	0.064 (4)	−0.002 (3)	0.017 (3)	0.002 (3)
C3	0.070 (3)	0.056 (3)	0.066 (3)	0.006 (3)	0.015 (3)	0.011 (3)
C4	0.059 (3)	0.054 (3)	0.058 (3)	0.002 (3)	0.002 (2)	−0.002 (3)
C5	0.065 (3)	0.063 (3)	0.061 (3)	0.002 (3)	0.010 (3)	0.008 (3)
C6	0.076 (4)	0.053 (3)	0.064 (3)	0.010 (3)	−0.001 (3)	−0.002 (3)
C7	0.061 (3)	0.080 (4)	0.066 (3)	0.007 (3)	0.005 (3)	−0.001 (3)
C8	0.069 (4)	0.069 (4)	0.064 (3)	0.011 (3)	0.007 (3)	−0.010 (3)
C9	0.089 (5)	0.090 (4)	0.100 (4)	0.025 (4)	0.017 (3)	−0.011 (3)
C10	0.082 (5)	0.113 (5)	0.118 (5)	0.036 (4)	0.008 (4)	−0.035 (5)
C11	0.125 (6)	0.082 (5)	0.104 (5)	0.040 (5)	−0.014 (5)	−0.015 (4)
C12	0.144 (6)	0.071 (4)	0.118 (5)	0.026 (4)	0.024 (4)	−0.005 (4)
C13	0.090 (4)	0.077 (4)	0.102 (4)	0.016 (3)	0.019 (4)	−0.010 (3)

Geometric parameters (Å, º)

O1—N1	1.229 (5)	C5—H5	0.9300
O2—N1	1.234 (5)	C6—H6	0.9300
N1—C1	1.453 (6)	C7—C8	1.464 (6)
N2—N3	1.362 (4)	C7—H7	0.9300
N2—C4	1.390 (5)	C8—C9	1.372 (6)
N2—H2A	0.90 (4)	C8—C13	1.382 (6)
N3—C7	1.283 (5)	C9—C10	1.410 (7)
C1—C2	1.375 (5)	C9—H9	0.9300
C1—C6	1.376 (6)	C10—C11	1.339 (8)
C2—C3	1.373 (5)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.356 (8)
C3—C4	1.400 (6)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.377 (6)
C4—C5	1.385 (5)	C12—H12	0.9300
C5—C6	1.372 (6)	C13—H13	0.9300
O1—N1—O2	122.8 (5)	C5—C6—H6	120.0
O1—N1—C1	118.2 (5)	C1—C6—H6	120.0
O2—N1—C1	118.9 (5)	N3—C7—C8	120.1 (5)
N3—N2—C4	118.8 (4)	N3—C7—H7	119.9
N3—N2—H2A	124 (3)	C8—C7—H7	119.9
C4—N2—H2A	117 (3)	C9—C8—C13	118.5 (5)
C7—N3—N2	116.5 (4)	C9—C8—C7	120.2 (5)
C2—C1—C6	121.4 (5)	C13—C8—C7	121.3 (5)
C2—C1—N1	119.3 (5)	C8—C9—C10	119.7 (6)
C6—C1—N1	119.3 (5)	C8—C9—H9	120.2
C3—C2—C1	119.1 (5)	C10—C9—H9	120.2
C3—C2—H2	120.4	C11—C10—C9	120.2 (6)
C1—C2—H2	120.4	C11—C10—H10	119.9
C2—C3—C4	119.9 (4)	C9—C10—H10	119.9
C2—C3—H3	120.0	C10—C11—C12	120.8 (6)
C4—C3—H3	120.0	C10—C11—H11	119.6
C5—C4—N2	118.4 (5)	C12—C11—H11	119.6
C5—C4—C3	120.1 (5)	C11—C12—C13	120.0 (6)
N2—C4—C3	121.5 (4)	C11—C12—H12	120.0
C6—C5—C4	119.4 (5)	C13—C12—H12	120.0
C6—C5—H5	120.3	C12—C13—C8	120.9 (5)
C4—C5—H5	120.3	C12—C13—H13	119.6
C5—C6—C1	120.1 (4)	C8—C13—H13	119.6
C4—N2—N3—C7	173.9 (4)	C4—C5—C6—C1	0.3 (7)
O1—N1—C1—C2	1.9 (6)	C2—C1—C6—C5	−0.1 (7)
O2—N1—C1—C2	−175.2 (5)	N1—C1—C6—C5	−179.1 (4)
O1—N1—C1—C6	−179.2 (4)	N2—N3—C7—C8	−178.7 (4)
O2—N1—C1—C6	3.7 (7)	N3—C7—C8—C9	171.2 (4)
C6—C1—C2—C3	−0.4 (7)	N3—C7—C8—C13	−6.1 (6)
N1—C1—C2—C3	178.5 (4)	C13—C8—C9—C10	−1.2 (6)
C1—C2—C3—C4	0.8 (6)	C7—C8—C9—C10	−178.5 (4)
N3—N2—C4—C5	−175.8 (4)	C8—C9—C10—C11	1.4 (8)
N3—N2—C4—C3	3.9 (6)	C9—C10—C11—C12	−0.5 (10)
C2—C3—C4—C5	−0.6 (6)	C10—C11—C12—C13	−0.6 (10)
C2—C3—C4—N2	179.7 (4)	C11—C12—C13—C8	0.7 (8)
N2—C4—C5—C6	179.8 (4)	C9—C8—C13—C12	0.2 (7)
C3—C4—C5—C6	0.1 (7)	C7—C8—C13—C12	177.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2^i	0.90 (4)	2.24 (4)	3.105 (5)	162 (4)

Symmetry code: (i) x−1, −y+1, z+1/2.