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The title compound, C13H12N4O6, containing a di­nitro­phenyl ring substituted on the pyrazole ring, was obtained by a reaction of ethyl aceto­acetate (2,4-di­nitro­phenyl)­hydrazone with Vilsmeier reagent. The benzene and pyrazole rings are oriented at an angle of 35.49 (6)° with respect to each other. The packing of the mol­ecules is controlled by intermolecular C—H...O hydrogen bonds, in addition to van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803024371/ci6292sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803024371/ci6292Isup2.hkl
Contains datablock I

CCDC reference: 227029

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.043
  • wR factor = 0.128
  • Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.99 PLAT432_ALERT_2_B Short Inter X...Y Contact O6 .. C4 = 2.89 Ang.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT430_ALERT_2_C Short Inter D...A Contact O6 .. O6 = 2.87 Ang.
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 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 1 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, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1997); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Ethyl 3-methyl-1-(2,4-dinitrophenyl)-1H-pyrazole-4-carboxylate top
Crystal data top
C13H12N4O6Z = 2
Mr = 320.27F(000) = 332
Triclinic, P1Dx = 1.464 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.7531 (8) ÅCell parameters from 1829 reflections
b = 9.7146 (10) Åθ = 2.0–28.0°
c = 11.4051 (12) ŵ = 0.12 mm1
α = 113.649 (2)°T = 293 K
β = 92.989 (2)°Block, pale yellow
γ = 109.089 (2)°0.21 × 0.19 × 0.18 mm
V = 726.74 (13) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3210 independent reflections
Radiation source: fine-focus sealed tube2600 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
ω scansθmax = 28.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 910
Tmin = 0.976, Tmax = 0.979k = 912
4623 measured reflectionsl = 1513
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128All H-atom parameters refined
S = 1.02 w = 1/[σ2(Fo2) + (0.0737P)2 + 0.0853P]
where P = (Fo2 + 2Fc2)/3
3210 reflections(Δ/σ)max = 0.001
256 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.20 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
O10.33971 (16)0.45890 (16)0.63006 (13)0.0591 (3)
O20.37071 (14)0.37774 (14)0.78603 (10)0.0470 (3)
O31.1906 (2)0.89878 (18)0.97845 (13)0.0784 (5)
O41.4153 (2)0.8115 (2)0.96059 (14)0.0792 (5)
O51.72140 (19)0.9461 (2)0.63105 (16)0.0941 (6)
O61.55237 (18)0.86268 (15)0.44242 (12)0.0570 (3)
N10.92725 (17)0.64369 (15)0.73161 (12)0.0412 (3)
N20.94311 (17)0.56952 (16)0.80975 (12)0.0434 (3)
N31.2894 (2)0.83692 (18)0.91575 (14)0.0563 (4)
N41.5707 (2)0.88453 (17)0.55618 (15)0.0516 (3)
C10.7702 (2)0.49489 (17)0.81583 (14)0.0394 (3)
C20.6410 (2)0.52023 (17)0.74120 (14)0.0390 (3)
C30.7471 (2)0.61362 (19)0.68814 (16)0.0428 (3)
C40.4361 (2)0.45189 (18)0.71271 (15)0.0416 (3)
C50.1724 (2)0.2805 (3)0.7542 (2)0.0565 (4)
C60.1462 (3)0.1804 (3)0.8273 (3)0.0745 (6)
C70.7330 (3)0.3934 (3)0.8881 (2)0.0536 (4)
C81.0868 (2)0.71899 (17)0.69331 (14)0.0392 (3)
C91.2630 (2)0.79859 (17)0.77585 (14)0.0415 (3)
C101.4224 (2)0.85295 (18)0.73264 (16)0.0442 (4)
C111.4026 (2)0.83283 (17)0.60573 (15)0.0429 (3)
C121.2299 (2)0.76324 (19)0.52269 (15)0.0441 (3)
C131.0726 (2)0.70505 (19)0.56639 (15)0.0439 (4)
H30.712 (3)0.655 (2)0.6306 (18)0.056 (5)*
H5A0.109 (3)0.355 (3)0.782 (2)0.070 (6)*
H5B0.129 (3)0.209 (3)0.655 (2)0.082 (7)*
H6A0.011 (4)0.108 (4)0.807 (3)0.106 (8)*
H6B0.213 (5)0.103 (4)0.794 (3)0.132 (11)*
H6C0.193 (5)0.240 (5)0.922 (4)0.145 (13)*
H7A0.853 (3)0.402 (3)0.931 (2)0.079 (6)*
H7B0.652 (3)0.282 (3)0.831 (2)0.071 (6)*
H7C0.665 (3)0.425 (3)0.947 (2)0.084 (7)*
H101.544 (3)0.906 (2)0.7896 (18)0.059 (5)*
H121.219 (3)0.749 (2)0.4315 (19)0.056 (5)*
H130.953 (3)0.649 (2)0.5087 (18)0.052 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0407 (6)0.0803 (8)0.0676 (8)0.0182 (6)0.0042 (5)0.0480 (7)
O20.0343 (5)0.0596 (7)0.0495 (6)0.0124 (5)0.0102 (4)0.0305 (5)
O30.0721 (9)0.0825 (10)0.0481 (7)0.0038 (8)0.0166 (7)0.0181 (7)
O40.0639 (8)0.1020 (11)0.0701 (9)0.0035 (8)0.0101 (7)0.0616 (9)
O50.0410 (7)0.1447 (16)0.0879 (11)0.0050 (9)0.0095 (7)0.0677 (11)
O60.0661 (8)0.0559 (7)0.0536 (7)0.0216 (6)0.0282 (6)0.0280 (6)
N10.0357 (6)0.0441 (7)0.0456 (7)0.0085 (5)0.0045 (5)0.0274 (5)
N20.0384 (7)0.0485 (7)0.0435 (7)0.0074 (5)0.0025 (5)0.0286 (6)
N30.0485 (8)0.0581 (8)0.0457 (8)0.0067 (7)0.0010 (6)0.0296 (7)
N40.0458 (8)0.0522 (8)0.0588 (9)0.0130 (6)0.0159 (6)0.0305 (7)
C10.0374 (7)0.0418 (7)0.0360 (7)0.0084 (6)0.0039 (6)0.0201 (6)
C20.0369 (7)0.0418 (7)0.0381 (7)0.0116 (6)0.0061 (6)0.0203 (6)
C30.0381 (8)0.0483 (8)0.0479 (8)0.0148 (6)0.0073 (6)0.0285 (7)
C40.0371 (7)0.0466 (8)0.0433 (8)0.0148 (6)0.0087 (6)0.0228 (6)
C50.0344 (8)0.0670 (11)0.0694 (12)0.0135 (8)0.0151 (8)0.0356 (10)
C60.0595 (13)0.0737 (14)0.0867 (16)0.0059 (11)0.0161 (11)0.0474 (13)
C70.0425 (9)0.0670 (12)0.0588 (11)0.0103 (8)0.0049 (8)0.0440 (9)
C80.0365 (7)0.0376 (7)0.0436 (8)0.0091 (6)0.0060 (6)0.0225 (6)
C90.0409 (8)0.0414 (7)0.0393 (7)0.0063 (6)0.0035 (6)0.0232 (6)
C100.0377 (8)0.0437 (8)0.0474 (8)0.0055 (6)0.0031 (6)0.0250 (7)
C110.0401 (8)0.0409 (8)0.0490 (8)0.0103 (6)0.0110 (6)0.0248 (6)
C120.0467 (8)0.0459 (8)0.0395 (8)0.0118 (7)0.0070 (6)0.0236 (6)
C130.0394 (8)0.0457 (8)0.0433 (8)0.0078 (7)0.0013 (6)0.0240 (7)
Geometric parameters (Å, º) top
O1—C41.2097 (18)C5—C61.490 (3)
O2—C41.3282 (18)C5—H5A0.96 (2)
O2—C51.451 (2)C5—H5B1.03 (2)
O3—N31.213 (2)C6—H6A1.01 (3)
O4—N31.218 (2)C6—H6B1.01 (4)
O5—N41.2172 (19)C6—H6C0.97 (4)
O6—N41.2202 (18)C7—H7A0.99 (2)
N1—C31.3514 (19)C7—H7B0.97 (2)
N1—N21.3749 (16)C7—H7C0.90 (3)
N1—C81.4061 (19)C8—C91.393 (2)
N2—C11.3195 (19)C8—C131.394 (2)
N3—C91.472 (2)C9—C101.377 (2)
N4—C111.465 (2)C10—C111.374 (2)
C1—C21.424 (2)C10—H100.96 (2)
C1—C71.492 (2)C11—C121.381 (2)
C2—C31.367 (2)C12—C131.376 (2)
C2—C41.467 (2)C12—H120.988 (19)
C3—H30.965 (19)C13—H130.956 (19)
C4—O2—C5118.11 (13)C5—C6—H6B109.2 (19)
C3—N1—N2111.83 (12)H6A—C6—H6B105 (2)
C3—N1—C8128.32 (12)C5—C6—H6C116 (2)
N2—N1—C8119.25 (11)H6A—C6—H6C110 (3)
C1—N2—N1105.14 (11)H6B—C6—H6C106 (3)
O3—N3—O4125.24 (17)C1—C7—H7A109.7 (14)
O3—N3—C9117.54 (15)C1—C7—H7B111.4 (13)
O4—N3—C9117.11 (17)H7A—C7—H7B112.4 (18)
O5—N4—O6123.61 (15)C1—C7—H7C110.3 (16)
O5—N4—C11117.90 (14)H7A—C7—H7C111 (2)
O6—N4—C11118.50 (14)H7B—C7—H7C102 (2)
N2—C1—C2110.73 (12)C9—C8—C13118.31 (14)
N2—C1—C7120.00 (13)C9—C8—N1121.87 (13)
C2—C1—C7129.18 (14)C13—C8—N1119.67 (13)
C3—C2—C1105.48 (13)C10—C9—C8121.85 (14)
C3—C2—C4124.67 (13)C10—C9—N3115.88 (13)
C1—C2—C4129.62 (13)C8—C9—N3122.20 (13)
N1—C3—C2106.80 (13)C11—C10—C9117.83 (14)
N1—C3—H3122.1 (11)C11—C10—H10120.7 (12)
C2—C3—H3131.1 (11)C9—C10—H10121.5 (11)
O1—C4—O2124.51 (14)C10—C11—C12122.30 (14)
O1—C4—C2123.86 (14)C10—C11—N4118.78 (14)
O2—C4—C2111.60 (12)C12—C11—N4118.91 (14)
O2—C5—C6106.50 (16)C13—C12—C11118.95 (14)
O2—C5—H5A107.0 (13)C13—C12—H12119.9 (11)
C6—C5—H5A111.9 (13)C11—C12—H12121.0 (11)
O2—C5—H5B109.9 (14)C12—C13—C8120.58 (14)
C6—C5—H5B111.4 (13)C12—C13—H13120.6 (11)
H5A—C5—H5B110.0 (18)C8—C13—H13118.7 (11)
C5—C6—H6A109.9 (16)
C3—N1—N2—C10.92 (17)N2—N1—C8—C13140.36 (14)
C8—N1—N2—C1172.80 (13)C13—C8—C9—C104.5 (2)
N1—N2—C1—C20.09 (16)N1—C8—C9—C10171.00 (14)
N1—N2—C1—C7176.91 (15)C13—C8—C9—N3172.35 (14)
N2—C1—C2—C30.73 (18)N1—C8—C9—N312.1 (2)
C7—C1—C2—C3175.72 (17)O3—N3—C9—C10129.84 (16)
N2—C1—C2—C4175.27 (14)O4—N3—C9—C1046.5 (2)
C7—C1—C2—C41.2 (3)O3—N3—C9—C847.2 (2)
N2—N1—C3—C21.39 (18)O4—N3—C9—C8136.41 (16)
C8—N1—C3—C2172.35 (14)C8—C9—C10—C112.8 (2)
C1—C2—C3—N11.24 (17)N3—C9—C10—C11174.25 (14)
C4—C2—C3—N1176.13 (14)C9—C10—C11—C121.1 (2)
C5—O2—C4—O18.4 (2)C9—C10—C11—N4177.87 (13)
C5—O2—C4—C2169.71 (14)O5—N4—C11—C101.3 (2)
C3—C2—C4—O17.0 (3)O6—N4—C11—C10178.21 (14)
C1—C2—C4—O1166.59 (16)O5—N4—C11—C12179.72 (17)
C3—C2—C4—O2174.84 (14)O6—N4—C11—C120.8 (2)
C1—C2—C4—O211.6 (2)C10—C11—C12—C133.1 (2)
C4—O2—C5—C6166.06 (17)N4—C11—C12—C13175.83 (14)
C3—N1—C8—C9154.49 (15)C11—C12—C13—C81.3 (2)
N2—N1—C8—C935.1 (2)C9—C8—C13—C122.4 (2)
C3—N1—C8—C1330.0 (2)N1—C8—C13—C12173.25 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6A···O5i1.00 (4)2.50 (3)3.358 (3)144 (2)
C13—H13···O1ii0.95 (2)2.34 (2)3.292 (2)173 (2)
Symmetry codes: (i) x2, y1, z; (ii) x+1, y+1, z+1.
 

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