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.
Supporting information
CCDC reference: 206787
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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.
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).
Crystal data top
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) Å3 | 0.58 × 0.38 × 0.30 mm |
Z = 2 | |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0473P)2 + 0.0138P] where P = (Fo2 + 2Fc2)/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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O2i | 0.86 | 2.36 | 3.215 (4) | 173 |
Symmetry code: (i) x−1, −y, z−1/2. |