Crystal structure and spectroscopic properties of (E)-1,3-dimethyl-2-[3-(4-nitro­phen­yl)triaz-2-enyl­idene]-2,3-di­hydro-1H-imidazole

The triazene derivative, (E)-1,3-dimethyl-2-[(4-nitro­phen­yl)triaz-2-enyl­idene]-2,3-di­hydro-1H-imidazole was synthesized by coupling 1,3-di­methyl­imidazolium iodide with 1-azido-4-nitro benzene. The title compound has monoclinic (C2/c) symmetry and an E conformation about the –N= N– bond.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.070
• wR factor = 0.158
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.3 Note
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     14.288 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.635 Check

Alert level G
PLAT013_ALERT_1_G N.O.K.   _shelx_hkl_checksum Found in CIF ......     Please Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   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
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2018); data reduction: SAINT (Bruker, 2018); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(E)-1,3-Dimethyl-2-[3-(4-nitrophenyl)triaz-2-enylidene]-2,3-dihydro-1H-imidazole

Crystal data

C11H12N6O2	F(000) = 1088
Mr = 260.27	Dx = 1.478 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 27.7311 (18) Å	Cell parameters from 4851 reflections
b = 7.1747 (9) Å	θ = 3.0–27.8°
c = 11.7849 (14) Å	µ = 0.11 mm^−1
β = 94.101 (4)°	T = 100 K
V = 2338.7 (4) Å^3	Plates, red
Z = 8	0.11 × 0.05 × 0.02 mm

Data collection

Bruker AXS D8 Quest diffractometer with PhotonII charge-integrating pixel array detector (CPAD)	2206 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.077
Absorption correction: multi-scan (SADABS; Bruker, 2018)	θmax = 27.9°, θmin = 2.9°
Tmin = 0.655, Tmax = 0.746	h = −36→36
23709 measured reflections	k = −9→9
2807 independent reflections	l = −15→15

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.070	H-atom parameters constrained
wR(F^2) = 0.158	w = 1/[σ^2(Fo^2) + (0.0623P)^2 + 4.2467P] where P = (Fo^2 + 2Fc^2)/3
S = 1.16	(Δ/σ)max < 0.001
2807 reflections	Δρmax = 0.36 e Å^−3
174 parameters	Δρmin = −0.37 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
O2	0.90725 (6)	0.6192 (3)	0.42545 (14)	0.0208 (4)
O1	0.91792 (6)	0.7705 (3)	0.58417 (15)	0.0231 (4)
N5	0.67583 (7)	0.4345 (3)	0.54983 (15)	0.0122 (4)
N3	0.60385 (7)	0.2903 (3)	0.39246 (15)	0.0133 (4)
N6	0.70494 (7)	0.4980 (3)	0.63041 (15)	0.0144 (4)
N1	0.55532 (7)	0.2913 (3)	0.52968 (16)	0.0163 (4)
N7	0.89267 (7)	0.6760 (3)	0.51636 (16)	0.0156 (4)
N4	0.63305 (7)	0.3932 (3)	0.58753 (15)	0.0147 (4)
C2	0.60118 (8)	0.3293 (3)	0.50481 (18)	0.0132 (5)
C8	0.75071 (8)	0.5395 (3)	0.59381 (18)	0.0131 (5)
C13	0.76739 (8)	0.4927 (3)	0.48705 (19)	0.0138 (5)
H13	0.746476	0.430092	0.432205	0.017*
C10	0.82858 (8)	0.6785 (3)	0.64889 (18)	0.0140 (5)
H10	0.849717	0.740951	0.703362	0.017*
C12	0.81359 (8)	0.5371 (3)	0.46184 (19)	0.0150 (5)
H12	0.824761	0.505139	0.390018	0.018*
C9	0.78212 (8)	0.6344 (3)	0.67289 (18)	0.0140 (5)
H9	0.771038	0.668868	0.744390	0.017*
C11	0.84393 (8)	0.6295 (3)	0.54293 (19)	0.0148 (5)
C7	0.64554 (8)	0.3132 (3)	0.32329 (18)	0.0157 (5)
H7A	0.656635	0.442877	0.327693	0.023*
H7B	0.635989	0.281514	0.243959	0.023*
H7C	0.671761	0.230600	0.352109	0.023*
C4	0.55897 (8)	0.2268 (4)	0.34928 (19)	0.0184 (5)
H4	0.550771	0.189696	0.272952	0.022*
C5	0.52938 (8)	0.2270 (4)	0.4335 (2)	0.0200 (5)
H5	0.496428	0.189691	0.428140	0.024*
C6	0.53830 (9)	0.3056 (4)	0.6434 (2)	0.0249 (6)
H6A	0.553996	0.209729	0.692393	0.037*
H6B	0.503190	0.287618	0.639429	0.037*
H6C	0.546263	0.429166	0.674856	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0169 (8)	0.0327 (10)	0.0134 (8)	−0.0025 (7)	0.0046 (6)	0.0010 (8)
O1	0.0202 (9)	0.0287 (10)	0.0195 (9)	−0.0084 (8)	−0.0042 (7)	−0.0001 (8)
N5	0.0143 (9)	0.0132 (9)	0.0092 (8)	0.0006 (7)	0.0006 (7)	0.0000 (7)
N3	0.0145 (9)	0.0185 (10)	0.0072 (8)	−0.0003 (8)	0.0022 (7)	0.0002 (7)
N6	0.0159 (10)	0.0204 (10)	0.0070 (8)	0.0011 (8)	0.0010 (7)	−0.0003 (8)
N1	0.0133 (9)	0.0269 (11)	0.0089 (9)	−0.0009 (8)	0.0009 (7)	0.0009 (8)
N7	0.0147 (9)	0.0192 (10)	0.0126 (9)	−0.0016 (8)	−0.0004 (7)	0.0040 (8)
N4	0.0136 (9)	0.0226 (10)	0.0080 (8)	0.0006 (8)	0.0013 (7)	−0.0019 (8)
C2	0.0158 (11)	0.0162 (11)	0.0076 (10)	0.0026 (9)	0.0002 (8)	0.0020 (8)
C8	0.0161 (11)	0.0134 (10)	0.0097 (10)	0.0022 (9)	0.0002 (8)	0.0015 (8)
C13	0.0149 (11)	0.0172 (11)	0.0090 (10)	−0.0015 (9)	−0.0004 (8)	−0.0032 (8)
C10	0.0174 (11)	0.0156 (11)	0.0084 (10)	0.0001 (9)	−0.0035 (8)	0.0003 (8)
C12	0.0180 (11)	0.0183 (11)	0.0088 (10)	0.0005 (9)	0.0014 (8)	0.0017 (9)
C9	0.0184 (11)	0.0177 (11)	0.0059 (9)	0.0032 (9)	0.0003 (8)	0.0008 (9)
C11	0.0146 (11)	0.0179 (11)	0.0118 (10)	−0.0005 (9)	−0.0007 (8)	0.0052 (9)
C7	0.0164 (11)	0.0238 (12)	0.0073 (10)	−0.0006 (9)	0.0047 (8)	−0.0004 (9)
C4	0.0171 (11)	0.0281 (13)	0.0096 (10)	−0.0009 (10)	−0.0024 (8)	−0.0011 (10)
C5	0.0146 (11)	0.0308 (14)	0.0141 (11)	−0.0040 (10)	−0.0032 (9)	0.0027 (10)
C6	0.0169 (11)	0.0473 (17)	0.0112 (11)	−0.0049 (12)	0.0063 (9)	−0.0017 (11)

Geometric parameters (Å, º)

O2—N7	1.241 (3)	C13—C12	1.373 (3)
O1—N7	1.228 (3)	C10—H10	0.9500
N5—N6	1.285 (3)	C10—C9	1.375 (3)
N5—N4	1.330 (3)	C10—C11	1.393 (3)
N3—C2	1.360 (3)	C12—H12	0.9500
N3—C7	1.471 (3)	C12—C11	1.395 (3)
N3—C4	1.387 (3)	C9—H9	0.9500
N6—C8	1.402 (3)	C7—H7A	0.9800
N1—C2	1.353 (3)	C7—H7B	0.9800
N1—C5	1.378 (3)	C7—H7C	0.9800
N1—C6	1.456 (3)	C4—H4	0.9500
N7—C11	1.448 (3)	C4—C5	1.332 (3)
N4—C2	1.348 (3)	C5—H5	0.9500
C8—C13	1.412 (3)	C6—H6A	0.9800
C8—C9	1.405 (3)	C6—H6B	0.9800
C13—H13	0.9500	C6—H6C	0.9800
N6—N5—N4	111.13 (17)	C11—C12—H12	120.4
C2—N3—C7	128.02 (19)	C8—C9—H9	119.3
C2—N3—C4	108.35 (18)	C10—C9—C8	121.4 (2)
C4—N3—C7	123.61 (18)	C10—C9—H9	119.3
N5—N6—C8	112.51 (18)	C10—C11—N7	119.1 (2)
C2—N1—C5	109.43 (19)	C10—C11—C12	121.7 (2)
C2—N1—C6	123.82 (19)	C12—C11—N7	119.2 (2)
C5—N1—C6	126.6 (2)	N3—C7—H7A	109.5
O2—N7—C11	118.54 (19)	N3—C7—H7B	109.5
O1—N7—O2	122.5 (2)	N3—C7—H7C	109.5
O1—N7—C11	118.95 (19)	H7A—C7—H7B	109.5
N5—N4—C2	112.85 (18)	H7A—C7—H7C	109.5
N1—C2—N3	106.65 (19)	H7B—C7—H7C	109.5
N4—C2—N3	134.0 (2)	N3—C4—H4	125.9
N4—C2—N1	119.30 (19)	C5—C4—N3	108.1 (2)
N6—C8—C13	125.8 (2)	C5—C4—H4	125.9
N6—C8—C9	115.53 (19)	N1—C5—H5	126.3
C9—C8—C13	118.6 (2)	C4—C5—N1	107.5 (2)
C8—C13—H13	119.7	C4—C5—H5	126.3
C12—C13—C8	120.5 (2)	N1—C6—H6A	109.5
C12—C13—H13	119.7	N1—C6—H6B	109.5
C9—C10—H10	120.7	N1—C6—H6C	109.5
C9—C10—C11	118.5 (2)	H6A—C6—H6B	109.5
C11—C10—H10	120.7	H6A—C6—H6C	109.5
C13—C12—H12	120.4	H6B—C6—H6C	109.5
C13—C12—C11	119.2 (2)
O2—N7—C11—C10	174.5 (2)	C13—C12—C11—N7	179.9 (2)
O2—N7—C11—C12	−5.6 (3)	C13—C12—C11—C10	−0.1 (3)
O1—N7—C11—C10	−5.8 (3)	C9—C8—C13—C12	0.9 (3)
O1—N7—C11—C12	174.2 (2)	C9—C10—C11—N7	179.7 (2)
N5—N6—C8—C13	−9.6 (3)	C9—C10—C11—C12	−0.3 (3)
N5—N6—C8—C9	171.13 (19)	C11—C10—C9—C8	1.0 (3)
N5—N4—C2—N3	3.5 (4)	C7—N3—C2—N1	178.1 (2)
N5—N4—C2—N1	−176.5 (2)	C7—N3—C2—N4	−1.8 (4)
N3—C4—C5—N1	0.3 (3)	C7—N3—C4—C5	−178.5 (2)
N6—N5—N4—C2	178.84 (19)	C4—N3—C2—N1	−0.3 (3)
N6—C8—C13—C12	−178.4 (2)	C4—N3—C2—N4	179.8 (3)
N6—C8—C9—C10	178.0 (2)	C5—N1—C2—N3	0.5 (3)
N4—N5—N6—C8	178.84 (18)	C5—N1—C2—N4	−179.6 (2)
C2—N3—C4—C5	0.0 (3)	C6—N1—C2—N3	176.7 (2)
C2—N1—C5—C4	−0.5 (3)	C6—N1—C2—N4	−3.4 (4)
C8—C13—C12—C11	−0.2 (3)	C6—N1—C5—C4	−176.5 (2)
C13—C8—C9—C10	−1.3 (3)