1,4-Di­chloro-1,4-di­phenyl-2,3-di­aza­buta-1,3-diene

The title mol­ecule, C₁₄H₁₀Cl₂N₂, shows a non-planar geometry, with the two phenyl rings oriented at an angle of 58.28 (9)° to each other. The crystal structure is stabilized by van der Waals interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.031
• wR factor = 0.090
• Data-to-parameter ratio = 13.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



ABSTM_02  Alert C The ratio of Tmax/Tmin expected RT(exp) is > 1.10
          Absorption corrections should be applied.
          Tmin and Tmax expected:      0.827     0.929
          RT(exp) =      1.124


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-NT (Bruker, 1997); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.

1,4-Dicholoro-1,4-diphenyl-2,3-diazabuta-1,3-diene

Crystal data

C14H10Cl2N2	F(000) = 568
Mr = 277.14	Dx = 1.439 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 39 reflections
a = 11.501 (1) Å	θ = 4.5–12.5°
b = 7.5319 (7) Å	µ = 0.49 mm^−1
c = 14.958 (2) Å	T = 293 K
β = 99.25 (1)°	Block, yellow
V = 1278.9 (2) Å^3	0.40 × 0.38 × 0.15 mm
Z = 4

Data collection

Bruker P4 diffractometer	Rint = 0.016
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.1°
Graphite monochromator	h = −13→1
θ–2θ scans	k = −8→1
3023 measured reflections	l = −17→17
2245 independent reflections	3 standard reflections every 97 reflections
1989 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0415P)^2 + 0.2899P] where P = (Fo^2 + 2Fc^2)/3
2245 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.24 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
Cl1	−0.08430 (4)	0.21123 (8)	0.99263 (3)	0.06572 (18)
Cl2	0.28150 (4)	0.10300 (7)	0.89364 (3)	0.06282 (17)
C1	0.12213 (14)	0.2160 (2)	0.74747 (10)	0.0401 (3)
C2	0.01576 (15)	0.2918 (2)	0.70963 (11)	0.0499 (4)
H2	−0.0310	0.3475	0.7466	0.060*
C3	−0.02099 (17)	0.2847 (3)	0.61708 (12)	0.0580 (5)
H3	−0.0923	0.3359	0.5918	0.070*
C4	0.04788 (18)	0.2018 (3)	0.56216 (11)	0.0564 (5)
H4	0.0226	0.1966	0.5000	0.068*
C5	0.15346 (18)	0.1271 (3)	0.59897 (12)	0.0558 (5)
H5	0.1997	0.0717	0.5616	0.067*
C6	0.19151 (15)	0.1338 (2)	0.69152 (11)	0.0477 (4)
H6	0.2633	0.0834	0.7163	0.057*
C7	0.15706 (14)	0.2229 (2)	0.84699 (10)	0.0410 (4)
N8	0.09567 (13)	0.3065 (2)	0.89567 (9)	0.0517 (4)
N9	0.13417 (13)	0.3097 (2)	0.98809 (9)	0.0493 (3)
C10	0.05800 (14)	0.2762 (2)	1.03816 (10)	0.0408 (4)
C11	0.08747 (13)	0.28433 (19)	1.13765 (10)	0.0381 (3)
C12	0.19232 (14)	0.3631 (2)	1.17667 (11)	0.0471 (4)
H12	0.2417	0.4130	1.1400	0.057*
C13	0.22384 (15)	0.3678 (3)	1.26970 (11)	0.0535 (4)
H13	0.2942	0.4212	1.2955	0.064*
C14	0.15125 (16)	0.2936 (3)	1.32443 (12)	0.0535 (4)
H14	0.1730	0.2961	1.3871	0.064*
C15	0.04697 (17)	0.2162 (3)	1.28649 (12)	0.0553 (5)
H15	−0.0019	0.1663	1.3236	0.066*
C16	0.01404 (15)	0.2119 (2)	1.19331 (11)	0.0483 (4)
H16	−0.0572	0.1605	1.1680	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0452 (3)	0.0959 (4)	0.0527 (3)	−0.0068 (2)	−0.0022 (2)	−0.0075 (2)
Cl2	0.0560 (3)	0.0770 (3)	0.0522 (3)	0.0179 (2)	−0.0012 (2)	−0.0019 (2)
C1	0.0429 (8)	0.0396 (8)	0.0388 (8)	−0.0055 (6)	0.0094 (6)	−0.0001 (6)
C2	0.0462 (9)	0.0624 (11)	0.0420 (8)	0.0061 (8)	0.0099 (7)	−0.0013 (8)
C3	0.0522 (10)	0.0745 (13)	0.0456 (9)	0.0056 (9)	0.0024 (8)	0.0023 (9)
C4	0.0684 (12)	0.0644 (11)	0.0365 (8)	−0.0099 (10)	0.0084 (8)	−0.0029 (8)
C5	0.0668 (12)	0.0575 (11)	0.0479 (9)	−0.0041 (9)	0.0236 (8)	−0.0073 (8)
C6	0.0479 (9)	0.0486 (9)	0.0489 (9)	0.0016 (7)	0.0144 (7)	−0.0019 (7)
C7	0.0402 (8)	0.0413 (8)	0.0420 (8)	−0.0036 (7)	0.0078 (7)	0.0022 (7)
N8	0.0539 (8)	0.0648 (9)	0.0367 (7)	0.0064 (7)	0.0081 (6)	−0.0010 (6)
N9	0.0502 (8)	0.0612 (9)	0.0366 (7)	0.0000 (7)	0.0071 (6)	−0.0029 (6)
C10	0.0403 (8)	0.0396 (8)	0.0421 (8)	0.0037 (6)	0.0057 (7)	−0.0035 (6)
C11	0.0381 (8)	0.0374 (8)	0.0391 (8)	0.0040 (6)	0.0069 (6)	−0.0011 (6)
C12	0.0430 (8)	0.0547 (10)	0.0447 (8)	−0.0060 (7)	0.0103 (7)	0.0001 (7)
C13	0.0465 (9)	0.0656 (11)	0.0459 (9)	−0.0063 (8)	0.0001 (7)	−0.0058 (8)
C14	0.0554 (10)	0.0670 (12)	0.0375 (8)	0.0040 (9)	0.0059 (7)	−0.0012 (8)
C15	0.0541 (10)	0.0696 (12)	0.0453 (9)	−0.0029 (9)	0.0173 (8)	0.0049 (8)
C16	0.0424 (9)	0.0553 (10)	0.0482 (9)	−0.0071 (7)	0.0096 (7)	−0.0014 (8)

Geometric parameters (Å, º)

Cl1—C10	1.7387 (16)	N8—N9	1.3822 (19)
Cl2—C7	1.7408 (16)	N9—C10	1.266 (2)
C1—C2	1.386 (2)	C10—C11	1.473 (2)
C1—C6	1.391 (2)	C11—C12	1.386 (2)
C1—C7	1.479 (2)	C11—C16	1.389 (2)
C2—C3	1.382 (2)	C12—C13	1.381 (2)
C2—H2	0.93	C12—H12	0.93
C3—C4	1.379 (3)	C13—C14	1.378 (3)
C3—H3	0.93	C13—H13	0.93
C4—C5	1.371 (3)	C14—C15	1.372 (3)
C4—H4	0.93	C14—H14	0.93
C5—C6	1.384 (2)	C15—C16	1.385 (2)
C5—H5	0.93	C15—H15	0.93
C6—H6	0.93	C16—H16	0.93
C7—N8	1.261 (2)
C2—C1—C6	119.45 (15)	C10—N9—N8	116.58 (14)
C2—C1—C7	118.41 (14)	N9—C10—C11	121.36 (14)
C6—C1—C7	122.13 (15)	N9—C10—Cl1	121.44 (13)
C3—C2—C1	120.07 (16)	C11—C10—Cl1	117.16 (11)
C3—C2—H2	120.0	C12—C11—C16	119.17 (14)
C1—C2—H2	120.0	C12—C11—C10	119.11 (14)
C4—C3—C2	120.12 (17)	C16—C11—C10	121.71 (14)
C4—C3—H3	119.9	C13—C12—C11	120.34 (15)
C2—C3—H3	119.9	C13—C12—H12	119.8
C5—C4—C3	120.22 (16)	C11—C12—H12	119.8
C5—C4—H4	119.9	C14—C13—C12	120.14 (16)
C3—C4—H4	119.9	C14—C13—H13	119.9
C4—C5—C6	120.26 (16)	C12—C13—H13	119.9
C4—C5—H5	119.9	C15—C14—C13	119.96 (16)
C6—C5—H5	119.9	C15—C14—H14	120.0
C5—C6—C1	119.88 (16)	C13—C14—H14	120.0
C5—C6—H6	120.1	C14—C15—C16	120.39 (16)
C1—C6—H6	120.1	C14—C15—H15	119.8
N8—C7—C1	120.79 (15)	C16—C15—H15	119.8
N8—C7—Cl2	121.88 (13)	C15—C16—C11	119.98 (16)
C1—C7—Cl2	117.26 (12)	C15—C16—H16	120.0
C7—N8—N9	117.83 (14)	C11—C16—H16	120.0