Intermolecular —CH₃...O₂N— contacts in two polymorphic modifications of (1E)-N'-[(E)-2-cyano-1-(dimethylamino)-2-nitrovinyl]-N,N-dimethyl­ethanimidamide

The title compound was synthesized and isolated in two crystal modifications. The structure of the orthorhombic modification was determined by the X-ray powder diffraction method and the structure of the monoclinic modification was determined using the X-ray single-crystal diffraction technique. The molecules in both polymorphs are E,E isomers. Intermolecular H₃C...NO₂ contacts and their role in the formation of the polymorphic modifications are analyzed.

Computing details

Program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

Figures

(1E)-N'-[2(E)-2-cyano-1-(dimethylamino)- 2-nitrovinyl]-N,N-dimethylethanimidamide

Crystal data

C9H15N5O2	Dx = 1.270 Mg m^−3
Mr = 225.26	Melting point = 142–144 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.844 (1) Å	Cell parameters from 25 reflections
b = 16.436 (1) Å	θ = 12–16°
c = 8.926 (1) Å	µ = 0.09 mm^−1
β = 114.81 (2)°	T = 313 K
V = 1177.7 (2) Å^3	Cubic, colourless
Z = 4	0.10 × 0.10 × 0.10 mm
F(000) = 480

Data collection

CAD4 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 2.5°
Graphite monochromator	h = −10→9
ω scans	k = 0→20
2298 measured reflections	l = 0→10
2298 independent reflections	2 standard reflections every 60 min
1343 reflections with I > 2σ(I)	intensity decay: 1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: difference Fourier map
wR(F^2) = 0.150	All H-atom parameters refined
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0715P)^2 + 0.1131P] where P = (Fo^2 + 2Fc^2)/3
2298 reflections	(Δ/σ)max = 0.022
206 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	−0.1792 (2)	0.16347 (14)	0.5037 (2)	0.0681 (7)
O2	−0.0277 (2)	0.11884 (15)	0.3822 (2)	0.0719 (7)
N1	0.1858 (2)	0.12887 (14)	0.9515 (3)	0.0478 (6)
N2	−0.0509 (3)	0.12912 (15)	0.5091 (3)	0.0514 (6)
N3	−0.0870 (2)	0.08831 (14)	0.8245 (3)	0.0488 (6)
N4	0.4494 (2)	0.17705 (13)	1.0663 (3)	0.0485 (6)
N5	0.3571 (3)	0.07410 (17)	0.6699 (3)	0.0697 (8)
C1	0.0528 (3)	0.10993 (16)	0.8120 (3)	0.0421 (6)
C2	0.0697 (3)	0.10408 (16)	0.6588 (3)	0.0433 (6)
C3	0.2946 (3)	0.18506 (16)	0.9553 (3)	0.0430 (6)
C4	0.2484 (5)	0.2597 (2)	0.8497 (4)	0.0596 (8)
C5	0.2263 (3)	0.08616 (16)	0.6618 (3)	0.0475 (7)
C6	0.5042 (5)	0.1018 (2)	1.1601 (5)	0.0672 (10)
C7	0.5768 (4)	0.2398 (2)	1.0974 (5)	0.0679 (9)
C8	−0.1105 (5)	0.1087 (3)	0.9728 (5)	0.0690 (10)
C9	−0.2153 (4)	0.0377 (2)	0.7027 (5)	0.0630 (9)
H4	0.272 (5)	0.308 (3)	0.923 (5)	0.118 (14)*
H41	0.136 (5)	0.260 (2)	0.782 (5)	0.093 (12)*
H42	0.309 (5)	0.258 (2)	0.781 (5)	0.102 (13)*
H6	0.469 (5)	0.101 (3)	1.253 (6)	0.128 (16)*
H61	0.616 (5)	0.097 (2)	1.213 (5)	0.118 (15)*
H62	0.441 (5)	0.059 (3)	1.104 (5)	0.116 (15)*
H7	0.598 (4)	0.250 (2)	0.998 (5)	0.104 (13)*
H71	0.671 (5)	0.226 (2)	1.185 (5)	0.107 (14)*
H72	0.538 (5)	0.295 (3)	1.122 (5)	0.141 (17)*
H8	−0.042 (7)	0.153 (3)	1.033 (7)	0.17 (2)*
H81	−0.081 (6)	0.070 (3)	1.042 (6)	0.16 (2)*
H82	−0.220 (7)	0.115 (3)	0.942 (6)	0.15 (2)*
H9	−0.173 (4)	0.010 (2)	0.629 (4)	0.081 (10)*
H91	−0.239 (4)	−0.005 (2)	0.768 (4)	0.100 (13)*
H92	−0.308 (5)	0.068 (2)	0.633 (5)	0.103 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0453 (11)	0.0925 (17)	0.0588 (13)	0.0210 (11)	0.0141 (10)	0.0061 (11)
O2	0.0649 (13)	0.1105 (19)	0.0402 (11)	0.0029 (12)	0.0219 (10)	−0.0009 (11)
N1	0.0423 (12)	0.0592 (15)	0.0407 (12)	−0.0060 (10)	0.0161 (10)	0.0010 (10)
N2	0.0422 (13)	0.0637 (16)	0.0439 (13)	0.0020 (11)	0.0139 (11)	−0.0017 (11)
N3	0.0401 (11)	0.0596 (15)	0.0498 (13)	−0.0052 (10)	0.0218 (10)	−0.0056 (11)
N4	0.0413 (12)	0.0518 (14)	0.0475 (13)	−0.0075 (10)	0.0139 (10)	−0.0002 (11)
N5	0.0524 (15)	0.086 (2)	0.0782 (19)	0.0140 (14)	0.0345 (14)	0.0050 (14)
C1	0.0361 (13)	0.0450 (15)	0.0421 (14)	0.0039 (11)	0.0135 (11)	0.0026 (12)
C2	0.0338 (12)	0.0524 (16)	0.0394 (14)	0.0020 (11)	0.0110 (11)	−0.0022 (12)
C3	0.0429 (14)	0.0525 (17)	0.0356 (13)	−0.0016 (12)	0.0183 (11)	−0.0032 (12)
C4	0.066 (2)	0.0498 (19)	0.0568 (19)	0.0018 (16)	0.0196 (18)	0.0004 (15)
C5	0.0481 (15)	0.0509 (17)	0.0434 (15)	0.0034 (13)	0.0190 (12)	0.0018 (12)
C6	0.0489 (19)	0.070 (2)	0.065 (2)	−0.0056 (18)	0.0065 (17)	0.0147 (19)
C7	0.0497 (19)	0.071 (3)	0.074 (2)	−0.0202 (17)	0.0172 (18)	−0.003 (2)
C8	0.064 (2)	0.095 (3)	0.062 (2)	−0.004 (2)	0.0408 (19)	−0.006 (2)
C9	0.0451 (17)	0.070 (2)	0.068 (2)	−0.0108 (16)	0.0182 (16)	−0.0101 (19)

Geometric parameters (Å, º)

O1—N2	1.250 (3)	C4—H4	0.99 (4)
O2—N2	1.245 (3)	C4—H41	0.92 (4)
N1—C3	1.324 (3)	C4—H42	0.97 (4)
N1—C1	1.342 (3)	C6—H6	1.00 (5)
N2—C2	1.377 (3)	C6—H61	0.90 (4)
N3—C1	1.335 (3)	C6—H62	0.90 (4)
N3—C9	1.458 (4)	C7—H7	0.99 (4)
N3—C8	1.462 (4)	C7—H71	0.90 (4)
N4—C3	1.317 (3)	C7—H72	1.03 (5)
N4—C6	1.458 (4)	C8—H8	0.96 (6)
N4—C7	1.466 (4)	C8—H81	0.85 (5)
N5—C5	1.146 (3)	C8—H82	0.89 (5)
C1—C2	1.441 (3)	C9—H9	1.00 (3)
C2—C5	1.405 (3)	C9—H91	0.99 (4)
C3—C4	1.496 (4)	C9—H92	0.93 (4)
C3—N1—C1	122.1 (2)	N5—C5—C2	176.9 (3)
O2—N2—O1	121.3 (2)	N4—C6—H6	110 (3)
O2—N2—C2	119.1 (2)	N4—C6—H61	114 (3)
O1—N2—C2	119.6 (2)	H6—C6—H61	102 (3)
C1—N3—C9	123.2 (2)	N4—C6—H62	111 (3)
C1—N3—C8	120.2 (2)	H6—C6—H62	97 (3)
C9—N3—C8	116.3 (3)	H61—C6—H62	120 (4)
C3—N4—C6	120.5 (2)	N4—C7—H7	111 (2)
C3—N4—C7	123.1 (3)	N4—C7—H71	110 (3)
C6—N4—C7	116.3 (3)	H7—C7—H71	111 (3)
N3—C1—N1	117.8 (2)	N4—C7—H72	111 (3)
N3—C1—C2	122.0 (2)	H7—C7—H72	105 (3)
N1—C1—C2	119.7 (2)	H71—C7—H72	108 (4)
N2—C2—C5	115.9 (2)	N3—C8—H8	112 (3)
N2—C2—C1	123.7 (2)	N3—C8—H81	112 (4)
C5—C2—C1	119.4 (2)	H8—C8—H81	103 (5)
N4—C3—N1	117.7 (2)	N3—C8—H82	107 (3)
N4—C3—C4	118.6 (3)	H8—C8—H82	116 (4)
N1—C3—C4	123.5 (2)	H81—C8—H82	106 (4)
C3—C4—H4	108 (2)	N3—C9—H9	111.3 (17)
C3—C4—H41	110 (2)	N3—C9—H91	105.1 (19)
H4—C4—H41	107 (3)	H9—C9—H91	107 (3)
C3—C4—H42	107 (2)	N3—C9—H92	113 (2)
H4—C4—H42	115 (3)	H9—C9—H92	106 (3)
H41—C4—H42	109 (3)	H91—C9—H92	115 (3)
C9—N3—C1—N1	−155.5 (3)	N3—C1—C2—N2	44.7 (4)
C8—N3—C1—N1	18.5 (4)	N1—C1—C2—N2	−142.9 (3)
C9—N3—C1—C2	17.0 (4)	N3—C1—C2—C5	−147.4 (3)
C8—N3—C1—C2	−169.0 (3)	N1—C1—C2—C5	25.0 (4)
C3—N1—C1—N3	−146.4 (2)	C6—N4—C3—N1	10.9 (4)
C3—N1—C1—C2	40.9 (4)	C7—N4—C3—N1	−172.2 (3)
O2—N2—C2—C5	14.4 (4)	C6—N4—C3—C4	−173.7 (3)
O1—N2—C2—C5	−163.8 (2)	C7—N4—C3—C4	3.3 (4)
O2—N2—C2—C1	−177.3 (3)	C1—N1—C3—N4	−151.2 (2)
O1—N2—C2—C1	4.5 (4)	C1—N1—C3—C4	33.6 (4)