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The structure of the title compound, C10H17N7O2, was determined using a bond-restrained Rietveld refinement which gave bond lengths and angles within the expected ranges. Although the two nearly planar (N,N-dimethylamino)methyleneamino groups are inclined at approximately 46° to the pyrazole ring, the conformations of the two amino chains are different, owing to either a repulsion effect of the pyrazole-methyl group or a short interatomic contact with the nitro group in one of the chains.
Supporting information
CCDC reference: 150862
Data collection: Johannson LS18 linescanner data collection program; cell refinement: LSPAID (Visser et al., 1986); data reduction: Philips Profile Fit (Philips, 1996); program(s) used to solve structure: MRIA (Zlokazov & Chernyshev, 1992); program(s) used to refine structure: MRIA; molecular graphics: PLUTON (Spek, 1997); software used to prepare material for publication: MRIA, SHELXL93 (Sheldrick, 1993) and PARST (Nardelli, 1983).
1-Methyl-3,5-di(
N,
N-dimethylaminomethylen)amino-4-nitropyrazol
top
Crystal data top
C10H17N7O2 | Z = 2 |
Mr = 267.31 | F(000) = 284 |
Triclinic, P1 | Dx = 1.301 Mg m−3 |
a = 9.577 (4) Å | Cu Kα1 radiation, λ = 1.54059 Å |
b = 9.972 (4) Å | µ = 0.80 mm−1 |
c = 7.602 (4) Å | T = 295 K |
α = 106.11 (3)° | Particle morphology: needles |
β = 95.12 (3)° | yellow |
γ = 78.22 (3)° | flat_sheet, 7 × 7 mm |
V = 682.4 (6) Å3 | |
Data collection top
Enraf-Nonius Guinier Johannson camera FR 552 diffractometer | Specimen mounting: pressed as a thin layer in the specimen holder of the camera |
Radiation source: Fine focus X-ray tube, Nonius 3502.223 | Data collection mode: transmission |
Quartz monochromator | Scan method: Stationary detector |
Refinement top
Refinement on Inet | 149 parameters |
Least-squares matrix: full with fixed elements per cycle | 63 restraints |
Rp = 0.068 | 17 constraints |
Rwp = 0.087 | H atoms treated by a mixture of independent and constrained refinement |
Rexp = 0.033 | Weighting scheme based on measured s.u.'s |
7101 data points | (Δ/σ)max = 0.05 |
Excluded region(s): 4.00 - 7.99 | Background function: Chebyshev polynomial up to the 5th order |
Profile function: split-type pseudo-Voigt | Preferred orientation correction: March-Dollase (Dollase, 1986) |
Special details top
Experimental. specimen was rotated in its plane |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.2844 (8) | 0.2175 (8) | 0.1494 (9) | 0.086 (2)* | |
C2 | 0.2381 (9) | 0.2000 (8) | 0.314 (1) | 0.086 (2)* | |
N3 | 0.1944 (7) | 0.3381 (7) | 0.4229 (7) | 0.086 (2)* | |
N4 | 0.1994 (6) | 0.4386 (6) | 0.3388 (7) | 0.086 (2)* | |
C5 | 0.2669 (7) | 0.3714 (8) | 0.1763 (9) | 0.086 (2)* | |
N6 | 0.3278 (6) | 0.1123 (6) | −0.0118 (7) | 0.086 (2)* | |
O7 | 0.3453 (5) | −0.0175 (4) | −0.0372 (6) | 0.086 (2)* | |
O8 | 0.3419 (5) | 0.1418 (5) | −0.1546 (5) | 0.086 (2)* | |
N9 | 0.2987 (6) | 0.4304 (6) | 0.0468 (7) | 0.086 (2)* | |
N10 | 0.2233 (6) | 0.0834 (7) | 0.3677 (7) | 0.086 (2)* | |
C11 | 0.1363 (9) | 0.3592 (8) | 0.601 (1) | 0.086 (2)* | |
C12 | 0.3277 (9) | −0.0317 (8) | 0.3374 (9) | 0.102 (2)* | |
C13 | 0.1999 (9) | 0.5439 (8) | 0.059 (1) | 0.102 (2)* | |
N14 | 0.3275 (7) | −0.1442 (7) | 0.4030 (8) | 0.102 (2)* | |
N15 | 0.2085 (8) | 0.6444 (7) | −0.0280 (7) | 0.102 (2)* | |
C16 | 0.450 (1) | −0.2592 (9) | 0.3821 (9) | 0.102 (2)* | |
C17 | 0.204 (1) | −0.1560 (8) | 0.489 (1) | 0.102 (2)* | |
C18 | 0.339 (1) | 0.6366 (8) | −0.119 (1) | 0.102 (2)* | |
C19 | 0.087 (1) | 0.756 (1) | −0.035 (1) | 0.102 (2)* | |
H20 | 0.109 (4) | 0.560 (4) | 0.129 (5) | 0.051* | |
H21 | 0.064 (4) | 0.294 (4) | 0.580 (5) | 0.051* | |
H22 | 0.223 (4) | 0.332 (4) | 0.684 (5) | 0.051* | |
H23 | 0.404 (5) | −0.034 (5) | 0.249 (5) | 0.051* | |
H24 | 0.091 (4) | 0.466 (4) | 0.644 (5) | 0.051* | |
H25 | 0.539 (5) | −0.212 (4) | 0.406 (5) | 0.051* | |
H26 | 0.444 (4) | −0.321 (4) | 0.249 (5) | 0.051* | |
H27 | 0.440 (5) | −0.312 (4) | 0.477 (5) | 0.051* | |
H28 | 0.118 (4) | −0.144 (4) | 0.399 (5) | 0.051* | |
H29 | 0.193 (5) | −0.075 (4) | 0.610 (5) | 0.051* | |
H30 | 0.226 (4) | −0.254 (4) | 0.514 (5) | 0.051* | |
H31 | 0.359 (4) | 0.537 (4) | −0.210 (5) | 0.051* | |
H32 | 0.418 (4) | 0.649 (4) | −0.016 (5) | 0.051* | |
H33 | 0.318 (5) | 0.718 (4) | −0.181 (5) | 0.051* | |
H34 | 0.060 (5) | 0.807 (4) | 0.098 (5) | 0.051* | |
H35 | 0.007 (5) | 0.707 (5) | −0.109 (5) | 0.051* | |
H36 | 0.120 (5) | 0.821 (4) | −0.100 (5) | 0.051* | |
Geometric parameters (Å, º) top
C1—N6 | 1.405 (8) | N15—C18 | 1.46 (1) |
C1—C2 | 1.43 (1) | C11—H21 | 1.02 (4) |
C1—C5 | 1.47 (1) | C11—H22 | 1.03 (4) |
C2—N10 | 1.37 (1) | C11—H24 | 1.03 (3) |
C2—N3 | 1.396 (9) | C12—H23 | 1.03 (5) |
N3—N4 | 1.34 (1) | C13—H20 | 1.02 (4) |
N3—C11 | 1.45 (1) | C16—H25 | 1.03 (5) |
N4—C5 | 1.378 (8) | C16—H26 | 1.03 (4) |
C5—N9 | 1.36 (1) | C16—H27 | 1.02 (5) |
N6—O8 | 1.226 (8) | C17—H28 | 1.03 (4) |
N6—O7 | 1.233 (7) | C17—H29 | 1.04 (3) |
N9—C13 | 1.306 (9) | C17—H30 | 1.02 (5) |
N10—C12 | 1.340 (9) | C18—H31 | 1.03 (4) |
C12—N14 | 1.35 (1) | C18—H32 | 1.03 (4) |
C13—N15 | 1.37 (1) | C18—H33 | 1.03 (5) |
N14—C17 | 1.44 (1) | C19—H34 | 1.03 (4) |
N14—C16 | 1.45 (1) | C19—H35 | 1.03 (5) |
N15—C19 | 1.44 (1) | C19—H36 | 1.03 (5) |
| | | |
C5—C1—N6 | 125.9 (7) | C12—N14—C17 | 121.1 (7) |
C2—C1—N6 | 128.3 (6) | C12—N14—C16 | 120.6 (7) |
C2—C1—C5 | 105.7 (6) | C16—N14—C17 | 118.3 (7) |
C1—C2—N10 | 133.1 (7) | C13—N15—C19 | 119.9 (7) |
C1—C2—N3 | 104.8 (6) | C13—N15—C18 | 119.9 (7) |
N3—C2—N10 | 122.0 (7) | C18—N15—C19 | 120.2 (7) |
C2—N3—C11 | 119.2 (6) | N14—C16—H27 | 106 (2) |
C2—N3—N4 | 113.6 (6) | N14—C16—H26 | 107 (2) |
N4—N3—C11 | 126.9 (6) | N14—C16—H25 | 106 (3) |
N3—N4—C5 | 107.1 (5) | H26—C16—H27 | 113 (3) |
C1—C5—N4 | 108.2 (6) | H25—C16—H27 | 113 (3) |
N4—C5—N9 | 128.3 (6) | H25—C16—H26 | 112 (3) |
C1—C5—N9 | 123.1 (7) | N14—C17—H30 | 106 (2) |
C1—N6—O8 | 122.0 (5) | N14—C17—H29 | 106 (2) |
C1—N6—O7 | 127.2 (6) | N14—C17—H28 | 107 (2) |
O7—N6—O8 | 110.5 (5) | H29—C17—H30 | 112 (3) |
C5—N9—C13 | 104.6 (6) | H28—C17—H30 | 113 (3) |
C2—N10—C12 | 119.8 (7) | H28—C17—H29 | 112 (3) |
N3—C11—H24 | 106 (2) | N15—C18—H33 | 106 (2) |
N3—C11—H22 | 106 (2) | N15—C18—H32 | 106 (3) |
N3—C11—H21 | 106 (2) | N15—C18—H31 | 106 (2) |
H22—C11—H24 | 112 (3) | H32—C18—H33 | 113 (3) |
H21—C11—H24 | 113 (3) | H31—C18—H33 | 113 (3) |
H21—C11—H22 | 113 (3) | H31—C18—H32 | 112 (3) |
N10—C12—H23 | 115 (3) | N15—C19—H36 | 106 (2) |
N10—C12—N14 | 123.0 (7) | N15—C19—H35 | 107 (3) |
N14—C12—H23 | 121 (2) | N15—C19—H34 | 107 (3) |
N9—C13—H20 | 122 (2) | H35—C19—H36 | 112 (3) |
N9—C13—N15 | 122.0 (7) | H34—C19—H36 | 112 (3) |
N15—C13—H20 | 116 (2) | H34—C19—H35 | 112 (3) |
| | | |
C2—C1—N6—O7 | −6 (1) | N10—C12—N14—C16 | −173.6 (7) |
C1—C2—N10—N14 | 52 (2) | N9—C13—N15—C19 | 169.8 (7) |
C1—C5—N9—C13 | 142.4 (7) | | |
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