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In the title compound, C13H8Cl2N4O4, the dinitro­phenyl­hydrazone and benzene ring planes are nearly coplanar, making a dihedral angle of 3.39 (9)°. There is an intra­molecular N—H...O inter­action and weak intermolecular C—H...O hydrogen-bonding inter­actions which stabilize the packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806022331/dn2045sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806022331/dn2045Isup2.hkl
Contains datablock I

CCDC reference: 613664

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.033
  • wR factor = 0.092
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

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Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - N3 .. 6.85 su PLAT431_ALERT_2_C Short Inter HL..A Contact Cl2 .. O1 .. 3.11 Ang.
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 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003).; software used to prepare material for publication: SHELXL97.

2,6-dichlorobenzaldehyde 2,4-dinitrophenylhydrazone top
Crystal data top
C13H8Cl2N4O4F(000) = 720
Mr = 355.13Dx = 1.639 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1237 reflections
a = 12.375 (2) Åθ = 2.3–24.5°
b = 7.928 (1) ŵ = 0.48 mm1
c = 14.977 (2) ÅT = 298 K
β = 101.588 (3)°Block, yellow
V = 1439.4 (4) Å30.31 × 0.28 × 0.25 mm
Z = 4
Data collection top
Bruker CCD area-detector
diffractometer
2984 independent reflections
Radiation source: fine-focus sealed tube2290 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ω scansθmax = 26.5°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1515
Tmin = 0.866, Tmax = 0.890k = 99
10917 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0489P)2]
where P = (Fo2 + 2Fc2)/3
2984 reflections(Δ/σ)max < 0.001
208 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.26 e Å3
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
xyzUiso*/Ueq
Cl10.39168 (4)0.16075 (7)0.05649 (4)0.06653 (18)
Cl20.19795 (4)0.10422 (7)0.21042 (3)0.06588 (18)
O10.00903 (11)0.22821 (19)0.23907 (8)0.0630 (4)
O20.14298 (12)0.3992 (2)0.28669 (8)0.0763 (4)
O30.36870 (12)0.61485 (18)0.09361 (10)0.0734 (4)
O40.31461 (12)0.60015 (19)0.05241 (10)0.0733 (4)
N10.12913 (10)0.12033 (16)0.01421 (8)0.0389 (3)
N20.06092 (10)0.17634 (17)0.06429 (8)0.0388 (3)
H20.07500.15280.11680.047*
N30.08307 (12)0.32243 (19)0.22525 (9)0.0480 (4)
N40.30484 (12)0.56660 (18)0.02548 (11)0.0504 (4)
C10.29621 (12)0.03077 (19)0.07763 (10)0.0379 (4)
C20.29771 (13)0.0123 (2)0.17099 (11)0.0439 (4)
C30.37738 (15)0.0869 (2)0.23749 (13)0.0577 (5)
H30.37560.07220.29880.069*
C40.45877 (17)0.1824 (3)0.21270 (15)0.0672 (6)
H40.51200.23290.25730.081*
C50.46227 (15)0.2039 (2)0.12273 (15)0.0619 (5)
H50.51780.26850.10620.074*
C60.38227 (13)0.1285 (2)0.05618 (12)0.0470 (4)
C70.21425 (12)0.0410 (2)0.00282 (10)0.0386 (4)
H70.22540.02750.05640.046*
C80.02877 (11)0.26936 (18)0.05717 (9)0.0331 (3)
C90.10088 (12)0.34223 (19)0.13291 (9)0.0358 (3)
C100.19104 (12)0.4391 (2)0.12239 (10)0.0395 (4)
H100.23760.48550.17290.047*
C110.21026 (12)0.46527 (19)0.03674 (10)0.0384 (4)
C120.14121 (12)0.39634 (19)0.03996 (11)0.0392 (4)
H120.15560.41520.09770.047*
C130.05284 (12)0.30149 (19)0.02964 (10)0.0370 (3)
H130.00710.25660.08100.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0571 (3)0.0780 (4)0.0698 (3)0.0055 (2)0.0252 (2)0.0204 (3)
Cl20.0768 (3)0.0837 (4)0.0392 (3)0.0249 (3)0.0165 (2)0.0010 (2)
O10.0613 (8)0.0952 (11)0.0360 (6)0.0137 (7)0.0181 (6)0.0020 (6)
O20.0841 (10)0.1084 (12)0.0326 (7)0.0217 (9)0.0028 (6)0.0172 (7)
O30.0596 (8)0.0794 (10)0.0752 (10)0.0244 (7)0.0012 (7)0.0021 (7)
O40.0781 (10)0.0818 (10)0.0671 (9)0.0273 (8)0.0315 (8)0.0010 (8)
N10.0387 (7)0.0439 (8)0.0330 (7)0.0009 (6)0.0047 (5)0.0020 (5)
N20.0401 (7)0.0496 (8)0.0268 (6)0.0025 (6)0.0071 (5)0.0006 (5)
N30.0484 (8)0.0649 (10)0.0294 (7)0.0074 (7)0.0045 (6)0.0042 (7)
N40.0474 (8)0.0444 (8)0.0599 (10)0.0035 (7)0.0123 (7)0.0019 (7)
C10.0364 (8)0.0329 (8)0.0440 (9)0.0036 (6)0.0074 (7)0.0021 (7)
C20.0467 (9)0.0385 (9)0.0454 (9)0.0003 (7)0.0068 (7)0.0007 (7)
C30.0633 (12)0.0534 (11)0.0506 (11)0.0020 (9)0.0023 (9)0.0038 (9)
C40.0604 (12)0.0601 (12)0.0703 (14)0.0102 (10)0.0130 (10)0.0036 (10)
C50.0421 (10)0.0532 (11)0.0859 (15)0.0107 (8)0.0023 (10)0.0068 (10)
C60.0403 (9)0.0423 (10)0.0585 (11)0.0041 (7)0.0102 (8)0.0095 (8)
C70.0416 (9)0.0395 (9)0.0352 (8)0.0011 (7)0.0087 (6)0.0044 (7)
C80.0345 (8)0.0332 (8)0.0317 (8)0.0067 (6)0.0069 (6)0.0000 (6)
C90.0383 (8)0.0415 (9)0.0271 (7)0.0086 (7)0.0054 (6)0.0001 (6)
C100.0389 (8)0.0395 (9)0.0371 (8)0.0052 (7)0.0004 (6)0.0057 (7)
C110.0376 (8)0.0358 (8)0.0421 (9)0.0010 (7)0.0087 (7)0.0004 (7)
C120.0444 (9)0.0409 (9)0.0337 (8)0.0033 (7)0.0113 (7)0.0016 (7)
C130.0402 (8)0.0407 (9)0.0288 (7)0.0019 (7)0.0039 (6)0.0027 (6)
Geometric parameters (Å, º) top
Cl1—C61.7335 (19)C3—C41.369 (3)
Cl2—C21.7374 (17)C3—H30.9300
O1—N31.2315 (18)C4—C51.367 (3)
O2—N31.2219 (18)C4—H40.9300
O3—N41.2198 (18)C5—C61.391 (3)
O4—N41.2260 (19)C5—H50.9300
N1—C71.2674 (19)C7—H70.9300
N1—N21.3759 (16)C8—C131.4141 (19)
N2—C81.3546 (18)C8—C91.418 (2)
N2—H20.8600C9—C101.389 (2)
N3—C91.4519 (19)C10—C111.367 (2)
N4—C111.457 (2)C10—H100.9300
C1—C21.402 (2)C11—C121.398 (2)
C1—C61.406 (2)C12—C131.361 (2)
C1—C71.467 (2)C12—H120.9300
C2—C31.385 (2)C13—H130.9300
C7—N1—N2115.40 (13)C5—C6—C1122.41 (17)
C8—N2—N1118.70 (12)C5—C6—Cl1117.20 (14)
C8—N2—H2120.6C1—C6—Cl1120.39 (13)
N1—N2—H2120.6N1—C7—C1123.74 (14)
O2—N3—O1122.34 (14)N1—C7—H7118.1
O2—N3—C9118.57 (15)C1—C7—H7118.1
O1—N3—C9119.09 (13)N2—C8—C13119.85 (13)
O3—N4—O4123.84 (15)N2—C8—C9123.57 (13)
O3—N4—C11118.46 (14)C13—C8—C9116.57 (13)
O4—N4—C11117.70 (14)C10—C9—C8121.69 (13)
C2—C1—C6115.26 (15)C10—C9—N3116.53 (13)
C2—C1—C7126.15 (14)C8—C9—N3121.76 (14)
C6—C1—C7118.60 (14)C11—C10—C9119.04 (14)
C3—C2—C1122.49 (16)C11—C10—H10120.5
C3—C2—Cl2115.74 (14)C9—C10—H10120.5
C1—C2—Cl2121.76 (12)C10—C11—C12121.28 (14)
C4—C3—C2119.80 (18)C10—C11—N4119.18 (14)
C4—C3—H3120.1C12—C11—N4119.54 (14)
C2—C3—H3120.1C13—C12—C11119.67 (14)
C5—C4—C3120.44 (17)C13—C12—H12120.2
C5—C4—H4119.8C11—C12—H12120.2
C3—C4—H4119.8C12—C13—C8121.75 (14)
C4—C5—C6119.60 (17)C12—C13—H13119.1
C4—C5—H5120.2C8—C13—H13119.1
C6—C5—H5120.2
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O10.862.012.6192 (16)127
C4—H4···O3i0.932.593.282 (2)132
C5—H5···O4ii0.932.593.509 (2)170
C7—H7···O2iii0.932.583.3723 (19)144
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+1, y1, z; (iii) x, y1/2, z1/2.
 

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