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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.
Supporting information
CCDC reference: 193753
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
top
Crystal data top
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) Å3 | 0.40 × 0.38 × 0.15 mm |
Z = 4 | |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.090 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0415P)2 + 0.2899P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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 |
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