(1-Phenyl-2,3-di­hydro-1H-benzimidazol-2-yl­idene)­malonodi­nitrile

The title compound, C₁₆H₁₀N₄, has been designed and synthesized for use as a new potential organic molecular electronic material. There are hydrogen bonds in the structure, which are responsible for the formation of linked pairs of molecules. Weak interactions are observed between antiparallel cyano substituents.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.059
• wR factor = 0.130
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C3       =       5.22 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2     -   C3       =       6.20 su
PLAT331_ALERT_2_C Small Av. Phenyl C-C Dist. C5     -   C10      =       1.37 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(I)

Crystal data

C16H10N4	F(000) = 536
Mr = 258.28	Dx = 1.333 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.377 (3) Å	Cell parameters from 950 reflections
b = 17.876 (5) Å	θ = 2.3–27.1°
c = 7.226 (2) Å	µ = 0.08 mm^−1
β = 106.235 (4)°	T = 293 K
V = 1286.9 (7) Å^3	Parallelepiped, colourless
Z = 4	0.15 × 0.10 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1556 reflections with I > 2σI)
Radiation source: fine-focus sealed tube	Rint = 0.051
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
φ and ω scans	h = −11→12
5318 measured reflections	k = −21→17
2260 independent reflections	l = −8→8

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0503P)^2 + 0.2084P] where P = (Fo^2 + 2Fc^2)/3
2260 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.18 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
C1	0.3952 (3)	0.07811 (14)	−0.1622 (4)	0.0435 (6)
C2	0.1984 (2)	0.02644 (16)	−0.3844 (4)	0.0507 (7)
C3	0.2550 (2)	0.06679 (15)	−0.2137 (4)	0.0447 (6)
C4	0.1682 (2)	0.09287 (13)	−0.1104 (3)	0.0400 (6)
C5	0.3328 (2)	0.14554 (14)	0.1818 (3)	0.0372 (6)
C6	0.4027 (2)	0.08612 (15)	0.2806 (4)	0.0488 (7)
H6	0.3648	0.0386	0.2661	0.059*
C7	0.5296 (3)	0.09728 (17)	0.4014 (4)	0.0545 (7)
H7	0.5780	0.0572	0.4685	0.065*
C8	0.5844 (3)	0.16735 (17)	0.4226 (4)	0.0520 (7)
H8	0.6701	0.1749	0.5047	0.062*
C9	0.5143 (3)	0.22595 (17)	0.3244 (4)	0.0558 (8)
H9	0.5526	0.2734	0.3392	0.067*
C10	0.3866 (2)	0.21587 (15)	0.2026 (4)	0.0475 (7)
H10	0.3383	0.2561	0.1361	0.057*
C11	0.0810 (2)	0.14743 (14)	0.1090 (3)	0.0408 (6)
C12	0.0594 (3)	0.18420 (16)	0.2643 (4)	0.0530 (7)
H12	0.1295	0.2056	0.3589	0.064*
C13	−0.0716 (3)	0.18788 (17)	0.2732 (4)	0.0607 (8)
H13	−0.0902	0.2124	0.3763	0.073*
C14	−0.1764 (3)	0.15594 (16)	0.1319 (4)	0.0576 (8)
H14	−0.2635	0.1595	0.1423	0.069*
C15	−0.1536 (2)	0.11917 (15)	−0.0230 (4)	0.0492 (7)
H15	−0.2235	0.0977	−0.1179	0.059*
C16	−0.0228 (2)	0.11546 (14)	−0.0319 (4)	0.0419 (6)
N1	0.5087 (2)	0.08546 (14)	−0.1296 (3)	0.0587 (7)
N2	0.1508 (2)	−0.00616 (16)	−0.5232 (4)	0.0700 (8)
N3	0.19954 (18)	0.13273 (11)	0.0570 (3)	0.0411 (5)
N4	0.03414 (19)	0.08345 (12)	−0.1644 (3)	0.0466 (6)
H4	−0.0100	0.0606	−0.2674	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0454 (17)	0.0440 (15)	0.0428 (15)	−0.0032 (12)	0.0152 (12)	−0.0102 (12)
C2	0.0320 (14)	0.0687 (19)	0.0550 (18)	−0.0018 (13)	0.0180 (13)	−0.0147 (16)
C3	0.0340 (14)	0.0577 (16)	0.0425 (14)	−0.0039 (12)	0.0105 (11)	−0.0153 (13)
C4	0.0335 (14)	0.0450 (14)	0.0401 (14)	−0.0014 (11)	0.0078 (11)	−0.0055 (12)
C5	0.0311 (13)	0.0463 (14)	0.0342 (13)	−0.0002 (11)	0.0090 (10)	−0.0082 (12)
C6	0.0425 (15)	0.0486 (16)	0.0541 (16)	−0.0048 (12)	0.0117 (13)	0.0011 (14)
C7	0.0448 (16)	0.065 (2)	0.0500 (17)	0.0086 (14)	0.0074 (13)	0.0131 (15)
C8	0.0335 (14)	0.081 (2)	0.0406 (15)	−0.0040 (14)	0.0082 (11)	−0.0079 (15)
C9	0.0492 (17)	0.0555 (18)	0.0595 (18)	−0.0114 (13)	0.0098 (14)	−0.0089 (15)
C10	0.0444 (15)	0.0429 (15)	0.0491 (16)	0.0005 (12)	0.0032 (12)	−0.0038 (13)
C11	0.0347 (14)	0.0465 (15)	0.0419 (15)	0.0001 (11)	0.0116 (11)	−0.0047 (12)
C12	0.0426 (15)	0.0670 (18)	0.0504 (17)	−0.0032 (13)	0.0146 (13)	−0.0198 (15)
C13	0.0542 (18)	0.078 (2)	0.0561 (18)	0.0041 (15)	0.0266 (15)	−0.0155 (16)
C14	0.0398 (15)	0.073 (2)	0.0642 (19)	0.0030 (14)	0.0216 (14)	−0.0066 (16)
C15	0.0353 (15)	0.0568 (17)	0.0542 (16)	−0.0035 (12)	0.0106 (12)	−0.0083 (14)
C16	0.0339 (14)	0.0475 (15)	0.0447 (15)	−0.0023 (11)	0.0118 (11)	−0.0092 (12)
N1	0.0400 (14)	0.0747 (17)	0.0643 (16)	−0.0079 (11)	0.0194 (11)	−0.0159 (13)
N2	0.0447 (15)	0.101 (2)	0.0626 (16)	−0.0084 (13)	0.0126 (12)	−0.0382 (16)
N3	0.0315 (11)	0.0508 (13)	0.0401 (12)	−0.0014 (9)	0.0086 (9)	−0.0113 (10)
N4	0.0322 (11)	0.0630 (15)	0.0430 (12)	−0.0056 (10)	0.0079 (9)	−0.0186 (11)

Geometric parameters (Å, º)

C1—N1	1.143 (3)	C9—C10	1.382 (3)
C1—C3	1.412 (4)	C9—H9	0.9300
C2—N2	1.146 (3)	C10—H10	0.9300
C2—C3	1.407 (4)	C11—C12	1.372 (4)
C3—C4	1.401 (3)	C11—C16	1.382 (3)
C4—N4	1.346 (3)	C11—N3	1.408 (3)
C4—N3	1.362 (3)	C12—C13	1.380 (4)
C5—C10	1.367 (3)	C12—H12	0.9300
C5—C6	1.369 (3)	C13—C14	1.390 (4)
C5—N3	1.443 (3)	C13—H13	0.9300
C6—C7	1.376 (3)	C14—C15	1.374 (4)
C6—H6	0.9300	C14—H14	0.9300
C7—C8	1.366 (4)	C15—C16	1.378 (3)
C7—H7	0.9300	C15—H15	0.9300
C8—C9	1.357 (4)	C16—N4	1.382 (3)
C8—H8	0.9300	N4—H4	0.8600
N1—C1—C3	176.3 (3)	C9—C10—H10	120.7
N2—C2—C3	179.2 (3)	C12—C11—C16	121.9 (2)
C4—C3—C2	117.7 (2)	C12—C11—N3	131.5 (2)
C4—C3—C1	125.5 (2)	C16—C11—N3	106.6 (2)
C2—C3—C1	116.8 (2)	C11—C12—C13	116.7 (2)
N4—C4—N3	107.1 (2)	C11—C12—H12	121.7
N4—C4—C3	124.7 (2)	C13—C12—H12	121.7
N3—C4—C3	128.2 (2)	C12—C13—C14	121.7 (3)
C10—C5—C6	121.0 (2)	C12—C13—H13	119.2
C10—C5—N3	120.4 (2)	C14—C13—H13	119.2
C6—C5—N3	118.6 (2)	C15—C14—C13	121.1 (2)
C5—C6—C7	119.5 (2)	C15—C14—H14	119.4
C5—C6—H6	120.3	C13—C14—H14	119.4
C7—C6—H6	120.3	C14—C15—C16	117.2 (2)
C8—C7—C6	119.9 (3)	C14—C15—H15	121.4
C8—C7—H7	120.0	C16—C15—H15	121.4
C6—C7—H7	120.0	C15—C16—C11	121.4 (2)
C9—C8—C7	120.2 (2)	C15—C16—N4	132.0 (2)
C9—C8—H8	119.9	C11—C16—N4	106.6 (2)
C7—C8—H8	119.9	C4—N3—C11	108.97 (19)
C8—C9—C10	120.7 (3)	C4—N3—C5	125.95 (19)
C8—C9—H9	119.6	C11—N3—C5	124.06 (19)
C10—C9—H9	119.6	C4—N4—C16	110.79 (19)
C5—C10—C9	118.6 (2)	C4—N4—H4	124.6
C5—C10—H10	120.7	C16—N4—H4	124.6

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N2^i	0.86	2.03	2.875 (3)	166
C9—H9···N1^ii	0.93	2.58	3.390 (4)	145

Symmetry codes: (i) −x, −y, −z−1; (ii) x, −y+1/2, z+1/2.