Salicyl­aldehyde 4-nitro­phenyl­hydrazone

Crystals of the title compound, C₁₃H₁₁N₃O₃, were obtained from a condensation reaction of salicyl­aldehyde and 4-nitro­phenyl­hydrazine. The mol­ecule exhibits a planar structure, with the 4-nitro group slightly inclined to the plane. The mol­ecules link to each other via intermolecular hydrogen bonding between the imino and nitro groups.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.032
• wR factor = 0.091
• Data-to-parameter ratio = 6.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           26.00
         From the CIF: _reflns_number_total               1190
         Count of symmetry unique reflns         1189
         Completeness (_total/calc)            100.08%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         1
         Fraction of Friedel pairs measured     0.001
         Are heavy atom types Z>Si present           no
          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.

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Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1985); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

C13H11N3O3	F(000) = 268
Mr = 257.25	Dx = 1.417 Mg m^−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 24 reflections
a = 5.0052 (11) Å	θ = 8.6–12.2°
b = 9.9004 (16) Å	µ = 0.10 mm^−1
c = 12.1749 (12) Å	T = 298 K
β = 92.199 (15)°	Plate, orange
V = 602.86 (17) Å^3	0.58 × 0.38 × 0.30 mm
Z = 2

Data collection

Rigaku AFC-7S diffractometer	Rint = 0.016
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 2.1°
Graphite monochromator	h = 0→6
ω/2θ scans	k = 0→12
1328 measured reflections	l = −15→15
1190 independent reflections	3 standard reflections every 150 reflections
774 reflections with I > 2σ(I)	intensity decay: 1.9%

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0473P)^2 + 0.0138P] where P = (Fo^2 + 2Fc^2)/3
1190 reflections	(Δ/σ)max = 0.009
172 parameters	Δρmax = 0.13 e Å^−3
2 restraints	Δρmin = −0.15 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	1.1219 (6)	0.0500 (3)	0.5900 (2)	0.0774 (8)
O2	1.1702 (6)	−0.1120 (3)	0.4758 (3)	0.0880 (10)
O3	−0.0249 (5)	0.5120 (2)	0.3978 (2)	0.0635 (7)
N1	1.0663 (6)	−0.0053 (3)	0.5016 (3)	0.0576 (8)
N2	0.2966 (5)	0.2283 (3)	0.2189 (2)	0.0479 (7)
H1	0.2781	0.1981	0.1528	0.057*
N3	0.1378 (5)	0.3308 (2)	0.2531 (2)	0.0446 (6)
C1	0.4849 (6)	0.1739 (3)	0.2897 (3)	0.0417 (7)
C2	0.6294 (7)	0.0607 (3)	0.2557 (3)	0.0515 (8)
H2	0.5952	0.0251	0.1859	0.062*
C3	0.8191 (6)	0.0024 (3)	0.3237 (3)	0.0529 (9)
H3	0.9124	−0.0730	0.3006	0.063*
C4	0.8723 (7)	0.0565 (3)	0.4277 (3)	0.0454 (7)
C5	0.7345 (6)	0.1688 (4)	0.4615 (3)	0.0509 (8)
H5	0.7724	0.2051	0.5308	0.061*
C6	0.5424 (6)	0.2272 (3)	0.3939 (3)	0.0481 (8)
H6	0.4500	0.3027	0.4176	0.058*
C7	−0.0384 (6)	0.3772 (3)	0.1848 (3)	0.0475 (8)
H7	−0.0531	0.3402	0.1146	0.057*
C8	−0.2189 (6)	0.4873 (3)	0.2140 (3)	0.0464 (8)
C9	−0.2040 (6)	0.5500 (3)	0.3169 (3)	0.0505 (8)
C10	−0.3793 (8)	0.6534 (4)	0.3392 (4)	0.0656 (11)
H10	−0.3685	0.6961	0.4072	0.079*
C11	−0.5690 (7)	0.6935 (4)	0.2618 (4)	0.0690 (11)
H11	−0.6864	0.7627	0.2784	0.083*
C12	−0.5887 (7)	0.6337 (4)	0.1604 (3)	0.0619 (10)
H12	−0.7185	0.6617	0.1086	0.074*
C13	−0.4131 (7)	0.5312 (3)	0.1361 (3)	0.0555 (9)
H13	−0.4241	0.4908	0.0672	0.067*
H9	0.0943	0.4491	0.3658	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0806 (18)	0.100 (2)	0.0505 (15)	0.0174 (17)	−0.0127 (13)	0.0054 (15)
O2	0.097 (2)	0.0724 (18)	0.093 (2)	0.0349 (18)	−0.0158 (17)	−0.0003 (16)
O3	0.0676 (15)	0.0649 (14)	0.0577 (13)	0.0085 (14)	−0.0021 (12)	−0.0073 (13)
N1	0.0542 (18)	0.0573 (19)	0.0612 (19)	0.0059 (16)	0.0000 (16)	0.0135 (16)
N2	0.0473 (14)	0.0471 (16)	0.0486 (16)	0.0079 (14)	−0.0065 (13)	−0.0080 (13)
N3	0.0436 (13)	0.0392 (14)	0.0509 (14)	0.0009 (13)	0.0011 (12)	0.0017 (12)
C1	0.0376 (16)	0.0391 (16)	0.0485 (17)	−0.0040 (14)	0.0041 (14)	−0.0024 (14)
C2	0.0492 (18)	0.0512 (18)	0.054 (2)	0.0034 (18)	−0.0056 (15)	−0.0148 (17)
C3	0.0493 (19)	0.0416 (17)	0.068 (2)	0.0077 (16)	−0.0002 (18)	−0.0060 (16)
C4	0.0427 (16)	0.0443 (17)	0.0493 (17)	0.0020 (15)	0.0016 (13)	0.0075 (16)
C5	0.056 (2)	0.053 (2)	0.0436 (18)	0.0015 (17)	−0.0015 (16)	−0.0027 (16)
C6	0.0518 (19)	0.0449 (17)	0.0473 (19)	0.0035 (16)	−0.0005 (16)	−0.0034 (16)
C7	0.0455 (17)	0.0481 (18)	0.0491 (18)	−0.0008 (17)	0.0037 (16)	0.0010 (16)
C8	0.0416 (16)	0.0447 (18)	0.0535 (18)	0.0000 (14)	0.0092 (15)	0.0102 (15)
C9	0.052 (2)	0.0454 (19)	0.054 (2)	−0.0012 (17)	0.0081 (17)	0.0060 (17)
C10	0.073 (3)	0.0493 (19)	0.075 (2)	0.006 (2)	0.016 (2)	−0.0067 (19)
C11	0.063 (2)	0.056 (2)	0.090 (3)	0.020 (2)	0.025 (2)	0.015 (2)
C12	0.051 (2)	0.063 (2)	0.072 (2)	0.0120 (19)	0.0103 (18)	0.027 (2)
C13	0.053 (2)	0.057 (2)	0.056 (2)	0.0059 (19)	0.0060 (17)	0.0123 (18)

Geometric parameters (Å, º)

O1—N1	1.229 (4)	C5—C6	1.370 (5)
O2—N1	1.224 (4)	C5—H5	0.930
O3—C9	1.359 (4)	C6—H6	0.930
O3—H9	0.956	C7—C8	1.468 (4)
N1—C4	1.436 (4)	C7—H7	0.930
N2—C1	1.364 (4)	C8—C9	1.398 (4)
N2—N3	1.364 (3)	C8—C13	1.401 (5)
N2—H1	0.860	C9—C10	1.382 (5)
N3—C7	1.274 (4)	C10—C11	1.371 (5)
C1—C6	1.394 (4)	C10—H10	0.930
C1—C2	1.404 (5)	C11—C12	1.368 (6)
C2—C3	1.364 (5)	C11—H11	0.930
C2—H2	0.930	C12—C13	1.382 (5)
C3—C4	1.391 (5)	C12—H12	0.930
C3—H3	0.930	C13—H13	0.930
C4—C5	1.379 (5)
C9—O3—H9	106.8	C5—C6—H6	119.9
O2—N1—O1	121.7 (3)	C1—C6—H6	119.9
O2—N1—C4	119.4 (3)	N3—C7—C8	121.8 (3)
O1—N1—C4	118.9 (3)	N3—C7—H7	119.1
C1—N2—N3	119.9 (3)	C8—C7—H7	119.1
C1—N2—H1	120.1	C9—C8—C13	118.7 (3)
N3—N2—H1	120.1	C9—C8—C7	122.3 (3)
C7—N3—N2	117.7 (3)	C13—C8—C7	118.9 (3)
N2—C1—C6	122.6 (3)	O3—C9—C10	118.0 (3)
N2—C1—C2	118.7 (3)	O3—C9—C8	122.5 (3)
C6—C1—C2	118.7 (3)	C10—C9—C8	119.5 (3)
C3—C2—C1	120.9 (3)	C11—C10—C9	120.6 (4)
C3—C2—H2	119.6	C11—C10—H10	119.7
C1—C2—H2	119.6	C9—C10—H10	119.7
C2—C3—C4	119.6 (3)	C12—C11—C10	121.2 (4)
C2—C3—H3	120.2	C12—C11—H11	119.4
C4—C3—H3	120.2	C10—C11—H11	119.4
C5—C4—C3	120.1 (3)	C11—C12—C13	119.1 (4)
C5—C4—N1	119.4 (3)	C11—C12—H12	120.5
C3—C4—N1	120.5 (3)	C13—C12—H12	120.5
C6—C5—C4	120.6 (3)	C12—C13—C8	120.9 (4)
C6—C5—H5	119.7	C12—C13—H13	119.6
C4—C5—H5	119.7	C8—C13—H13	119.6
C5—C6—C1	120.1 (3)
C1—N2—N3—C7	−178.8 (3)	C2—C1—C6—C5	−0.7 (4)
N3—N2—C1—C6	−6.6 (4)	N2—N3—C7—C8	179.9 (2)
N3—N2—C1—C2	174.4 (3)	N3—C7—C8—C9	1.7 (4)
N2—C1—C2—C3	−179.8 (3)	N3—C7—C8—C13	−178.3 (3)
C6—C1—C2—C3	1.1 (5)	C13—C8—C9—O3	178.8 (3)
C1—C2—C3—C4	−0.7 (5)	C7—C8—C9—O3	−1.2 (5)
C2—C3—C4—C5	−0.3 (5)	C13—C8—C9—C10	−0.2 (4)
C2—C3—C4—N1	178.4 (3)	C7—C8—C9—C10	179.8 (3)
O2—N1—C4—C5	173.1 (3)	O3—C9—C10—C11	−178.3 (3)
O1—N1—C4—C5	−6.2 (5)	C8—C9—C10—C11	0.8 (5)
O2—N1—C4—C3	−5.5 (5)	C9—C10—C11—C12	−0.6 (6)
O1—N1—C4—C3	175.1 (3)	C10—C11—C12—C13	−0.2 (5)
C3—C4—C5—C6	0.7 (5)	C11—C12—C13—C8	0.7 (5)
N1—C4—C5—C6	−177.9 (3)	C9—C8—C13—C12	−0.5 (5)
C4—C5—C6—C1	−0.3 (5)	C7—C8—C13—C12	179.4 (3)
N2—C1—C6—C5	−179.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H9···N3	0.956	1.823	2.664 (3)	145
N2—H1···O2^i	0.86	2.36	3.215 (4)	173

Symmetry code: (i) x−1, −y, z−1/2.