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Crystals of the title compound, C15H14ClN3O4, were obtained from a condensation reaction of 2-chloro-3,4-dimethoxybenzaldehyde and 4-dinitrophenylhydrazine. Within the nitrophenyl moiety, the distances of 1.401 (2) and 1.399 (2) Å for the two C—C bonds adjacent to the imino group are appreciably longer than the average distance of 1.377 (2) Å for the other aromatic C—C bonds in the same benzene ring. The crystal packing involves π–π stacking effects.
Supporting information
CCDC reference: 248802
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.028
- wR factor = 0.078
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
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 27.40
From the CIF: _reflns_number_total 3216
Count of symmetry unique reflns 1761
Completeness (_total/calc) 182.62%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1455
Fraction of Friedel pairs measured 0.826
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
0 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); 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).
2-Chloro-3,4-dimethoxybenzaldehyde (4-nitrophenyl)hydrazone
top
Crystal data top
C15H14ClN3O4 | F(000) = 696 |
Mr = 335.74 | Dx = 1.439 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 5900 reflections |
a = 16.4537 (10) Å | θ = 2.5–25.0° |
b = 8.1471 (11) Å | µ = 0.27 mm−1 |
c = 14.5814 (12) Å | T = 295 K |
β = 127.535 (12)° | Prism, orange |
V = 1550.0 (4) Å3 | 0.50 × 0.46 × 0.38 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 3071 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.016 |
Graphite monochromator | θmax = 27.4°, θmin = 2.9° |
Detector resolution: 10.00 pixels mm-1 | h = −21→21 |
ω scans | k = −10→10 |
6761 measured reflections | l = −18→18 |
3216 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.028 | w = 1/[σ2(Fo2) + (0.0571P)2 + 0.0873P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.078 | (Δ/σ)max = 0.001 |
S = 1.03 | Δρmax = 0.16 e Å−3 |
3216 reflections | Δρmin = −0.15 e Å−3 |
209 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
2 restraints | Extinction coefficient: 0.0073 (8) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1455 Friedel Pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.09 (4) |
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 | |
Cl | 0.44637 (4) | −0.15401 (4) | 0.06247 (4) | 0.05825 (13) | |
O1 | 0.25282 (14) | 1.03537 (16) | 0.25904 (15) | 0.0772 (4) | |
O2 | 0.21685 (14) | 0.9005 (2) | 0.35659 (16) | 0.0830 (5) | |
O3 | 0.51780 (9) | −0.12816 (13) | −0.07655 (10) | 0.0471 (2) | |
O4 | 0.58736 (11) | 0.13857 (15) | −0.11383 (11) | 0.0558 (3) | |
N1 | 0.37370 (12) | 0.32405 (16) | 0.22007 (12) | 0.0478 (3) | |
H1 | 0.3710 | 0.2343 | 0.2492 | 0.057* | |
N2 | 0.41001 (10) | 0.32317 (17) | 0.15747 (11) | 0.0444 (3) | |
N3 | 0.24760 (12) | 0.90589 (19) | 0.29913 (14) | 0.0576 (4) | |
C1 | 0.34147 (11) | 0.46878 (17) | 0.23651 (12) | 0.0390 (3) | |
C2 | 0.30626 (13) | 0.46636 (19) | 0.30309 (14) | 0.0476 (3) | |
H2 | 0.3040 | 0.3680 | 0.3338 | 0.057* | |
C3 | 0.27514 (13) | 0.6095 (2) | 0.32298 (14) | 0.0488 (3) | |
H3 | 0.2515 | 0.6087 | 0.3669 | 0.059* | |
C4 | 0.27940 (12) | 0.75507 (18) | 0.27698 (14) | 0.0456 (3) | |
C5 | 0.31223 (13) | 0.75866 (18) | 0.20969 (14) | 0.0477 (3) | |
H5 | 0.3137 | 0.8574 | 0.1788 | 0.057* | |
C6 | 0.34274 (12) | 0.6164 (2) | 0.18844 (13) | 0.0442 (3) | |
H6 | 0.3641 | 0.6181 | 0.1423 | 0.053* | |
C7 | 0.44234 (13) | 0.18549 (19) | 0.14934 (14) | 0.0452 (3) | |
H7 | 0.4401 | 0.0925 | 0.1847 | 0.054* | |
C8 | 0.48302 (11) | 0.17545 (17) | 0.08373 (12) | 0.0393 (3) | |
C9 | 0.48798 (11) | 0.02651 (17) | 0.04006 (12) | 0.0385 (3) | |
C10 | 0.52255 (11) | 0.01684 (18) | −0.02598 (11) | 0.0381 (3) | |
C11 | 0.55561 (12) | 0.16007 (18) | −0.04752 (13) | 0.0413 (3) | |
C12 | 0.55324 (12) | 0.30851 (19) | −0.00285 (14) | 0.0448 (3) | |
H12 | 0.5762 | 0.4036 | −0.0158 | 0.054* | |
C13 | 0.51669 (12) | 0.31525 (18) | 0.06104 (13) | 0.0428 (3) | |
H13 | 0.5146 | 0.4159 | 0.0896 | 0.051* | |
C14 | 0.61375 (17) | −0.2116 (3) | −0.0206 (2) | 0.0677 (5) | |
H14A | 0.6036 | −0.3115 | −0.0613 | 0.102* | |
H14B | 0.6410 | −0.2366 | 0.0577 | 0.102* | |
H14C | 0.6610 | −0.1425 | −0.0206 | 0.102* | |
C15 | 0.62752 (15) | 0.2793 (3) | −0.13279 (17) | 0.0604 (4) | |
H15A | 0.6468 | 0.2492 | −0.1808 | 0.091* | |
H15B | 0.6865 | 0.3194 | −0.0599 | 0.091* | |
H15C | 0.5761 | 0.3635 | −0.1704 | 0.091* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl | 0.0851 (3) | 0.04040 (17) | 0.0710 (2) | −0.0090 (2) | 0.0588 (2) | 0.00015 (18) |
O1 | 0.0893 (10) | 0.0389 (6) | 0.0956 (11) | 0.0087 (6) | 0.0523 (9) | 0.0016 (6) |
O2 | 0.1035 (13) | 0.0643 (8) | 0.1128 (13) | 0.0137 (8) | 0.0821 (12) | −0.0093 (9) |
O3 | 0.0523 (6) | 0.0420 (5) | 0.0509 (6) | −0.0063 (4) | 0.0335 (5) | −0.0119 (4) |
O4 | 0.0707 (8) | 0.0542 (6) | 0.0669 (7) | −0.0086 (5) | 0.0545 (7) | −0.0032 (5) |
N1 | 0.0637 (8) | 0.0410 (6) | 0.0555 (7) | 0.0097 (6) | 0.0449 (7) | 0.0091 (5) |
N2 | 0.0485 (7) | 0.0477 (7) | 0.0443 (6) | 0.0074 (5) | 0.0321 (6) | 0.0030 (5) |
N3 | 0.0525 (8) | 0.0446 (7) | 0.0649 (9) | 0.0040 (6) | 0.0302 (7) | −0.0076 (6) |
C1 | 0.0380 (6) | 0.0389 (6) | 0.0390 (6) | 0.0019 (5) | 0.0229 (6) | 0.0005 (5) |
C2 | 0.0586 (9) | 0.0395 (7) | 0.0567 (9) | 0.0019 (6) | 0.0413 (8) | 0.0037 (6) |
C3 | 0.0553 (9) | 0.0466 (8) | 0.0557 (9) | 0.0023 (7) | 0.0395 (8) | −0.0011 (6) |
C4 | 0.0391 (7) | 0.0399 (7) | 0.0491 (8) | 0.0020 (6) | 0.0225 (6) | −0.0044 (6) |
C5 | 0.0484 (8) | 0.0382 (7) | 0.0519 (8) | 0.0009 (6) | 0.0282 (7) | 0.0047 (6) |
C6 | 0.0463 (8) | 0.0446 (7) | 0.0474 (8) | 0.0010 (6) | 0.0314 (7) | 0.0047 (6) |
C7 | 0.0519 (8) | 0.0431 (7) | 0.0440 (7) | 0.0028 (6) | 0.0310 (7) | 0.0022 (6) |
C8 | 0.0401 (7) | 0.0396 (7) | 0.0378 (7) | 0.0028 (5) | 0.0235 (6) | 0.0016 (5) |
C9 | 0.0431 (7) | 0.0327 (6) | 0.0400 (7) | −0.0031 (5) | 0.0254 (6) | 0.0012 (5) |
C10 | 0.0396 (7) | 0.0367 (7) | 0.0370 (6) | −0.0037 (5) | 0.0228 (6) | −0.0028 (5) |
C11 | 0.0413 (7) | 0.0434 (7) | 0.0423 (7) | −0.0031 (6) | 0.0271 (6) | −0.0004 (5) |
C12 | 0.0449 (8) | 0.0380 (7) | 0.0528 (8) | −0.0056 (6) | 0.0305 (7) | 0.0008 (6) |
C13 | 0.0439 (8) | 0.0349 (6) | 0.0479 (8) | −0.0010 (6) | 0.0271 (6) | −0.0039 (5) |
C14 | 0.0718 (12) | 0.0506 (9) | 0.0811 (13) | 0.0116 (9) | 0.0468 (11) | −0.0031 (9) |
C15 | 0.0648 (11) | 0.0680 (11) | 0.0672 (10) | −0.0096 (9) | 0.0498 (9) | 0.0034 (9) |
Geometric parameters (Å, º) top
Cl—C9 | 1.7352 (14) | C5—C6 | 1.371 (2) |
O1—N3 | 1.234 (2) | C5—H5 | 0.9300 |
O2—N3 | 1.215 (2) | C6—H6 | 0.9300 |
O3—C10 | 1.3694 (17) | C7—C8 | 1.466 (2) |
O3—C14 | 1.432 (2) | C7—H7 | 0.9300 |
O4—C11 | 1.3616 (18) | C8—C13 | 1.392 (2) |
O4—C15 | 1.432 (2) | C8—C9 | 1.396 (2) |
N1—N2 | 1.3619 (17) | C9—C10 | 1.3873 (18) |
N1—C1 | 1.3725 (18) | C10—C11 | 1.402 (2) |
N1—H1 | 0.8600 | C11—C12 | 1.385 (2) |
N2—C7 | 1.278 (2) | C12—C13 | 1.384 (2) |
N3—C4 | 1.447 (2) | C12—H12 | 0.9300 |
C1—C2 | 1.401 (2) | C13—H13 | 0.9300 |
C1—C6 | 1.399 (2) | C14—H14A | 0.9600 |
C2—C3 | 1.374 (2) | C14—H14B | 0.9600 |
C2—H2 | 0.9300 | C14—H14C | 0.9600 |
C3—C4 | 1.385 (2) | C15—H15A | 0.9600 |
C3—H3 | 0.9300 | C15—H15B | 0.9600 |
C4—C5 | 1.379 (3) | C15—H15C | 0.9600 |
| | | |
C10—O3—C14 | 114.91 (14) | C13—C8—C9 | 117.43 (13) |
C11—O4—C15 | 117.13 (13) | C13—C8—C7 | 121.03 (13) |
N2—N1—C1 | 119.70 (12) | C9—C8—C7 | 121.53 (13) |
N2—N1—H1 | 120.1 | C10—C9—C8 | 121.92 (13) |
C1—N1—H1 | 120.1 | C10—C9—Cl | 117.27 (11) |
C7—N2—N1 | 116.38 (13) | C8—C9—Cl | 120.77 (11) |
O2—N3—O1 | 122.41 (15) | O3—C10—C9 | 120.65 (13) |
O2—N3—C4 | 118.82 (16) | O3—C10—C11 | 120.01 (12) |
O1—N3—C4 | 118.77 (16) | C9—C10—C11 | 119.18 (13) |
N1—C1—C6 | 121.73 (13) | O4—C11—C12 | 125.38 (13) |
N1—C1—C2 | 118.40 (13) | O4—C11—C10 | 114.91 (13) |
C6—C1—C2 | 119.87 (13) | C12—C11—C10 | 119.70 (13) |
C3—C2—C1 | 119.93 (14) | C13—C12—C11 | 119.96 (13) |
C3—C2—H2 | 120.0 | C13—C12—H12 | 120.0 |
C1—C2—H2 | 120.0 | C11—C12—H12 | 120.0 |
C2—C3—C4 | 119.29 (14) | C12—C13—C8 | 121.79 (13) |
C2—C3—H3 | 120.4 | C12—C13—H13 | 119.1 |
C4—C3—H3 | 120.4 | C8—C13—H13 | 119.1 |
C5—C4—C3 | 121.34 (14) | O3—C14—H14A | 109.5 |
C5—C4—N3 | 119.50 (15) | O3—C14—H14B | 109.5 |
C3—C4—N3 | 119.15 (16) | H14A—C14—H14B | 109.5 |
C6—C5—C4 | 119.92 (14) | O3—C14—H14C | 109.5 |
C6—C5—H5 | 120.0 | H14A—C14—H14C | 109.5 |
C4—C5—H5 | 120.0 | H14B—C14—H14C | 109.5 |
C5—C6—C1 | 119.62 (14) | O4—C15—H15A | 109.5 |
C5—C6—H6 | 120.2 | O4—C15—H15B | 109.5 |
C1—C6—H6 | 120.2 | H15A—C15—H15B | 109.5 |
N2—C7—C8 | 119.40 (14) | O4—C15—H15C | 109.5 |
N2—C7—H7 | 120.3 | H15A—C15—H15C | 109.5 |
C8—C7—H7 | 120.3 | H15B—C15—H15C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.86 | 2.36 | 2.8975 (19) | 121 |
Symmetry code: (i) x, −y, z+1/2. |
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