3,5-Bis[(N,N-di­methyl­amino)­methyl­ene­amino]-1-methyl-4-nitro­pyrazole from X-ray powder diffraction data

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.

Computing details

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

Crystal data

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) Å^3

Data collection

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

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

Experimental. specimen was rotated in its plane

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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)

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)