Crystal structure and Hirshfeld surface analysis of (E)-1-(4-chloro­phen­yl)-2-[2,2-di­chloro-1-(4-fluoro­phen­yl)ethen­yl]diazene

The dihedral angle between the 4-fluoro­phenyl ring and the 4-chloro­phenyl ring is 56.13 (13)°. In the crystal, mol­ecules are linked by C—H...Cl hydrogen bonds stacking in a column along the a axis. The crystal packing is further stabilized by face-to-face π–π stacking inter­actions between the centres of the similar aromatic rings of the adjacent mol­ecules.

Key indicators

• Single-crystal synchrotron study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.053
• wR factor = 0.142
• Data-to-parameter ratio = 16.4

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
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
ABSMU01_ALERT_1_G  Calculation of _exptl_absorpt_correction_mu
                not performed for this radiation type.
PLAT092_ALERT_4_G Check: Wavelength Given is not Cu,Ga,Mo,Ag,In Ka    0.80246 Ang.
PLAT434_ALERT_2_G Short Inter HL..HL Contact Cl1      ..Cl3              3.38 Ang.
                                            -x,-1/2+y,1/2-z  =      2_545 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact Cl1      ..Cl3              3.38 Ang.
                                           1-x,-1/2+y,1/2-z  =      2_645 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         11 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          2 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          9 Note
PLAT954_ALERT_1_G Reported (CIF) and Actual (FCF) Kmax Differ by .          1 Units

   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
   9 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: Marccd (Doyle, 2011); cell refinement: iMosflm (Battye et al., 2011); data reduction: iMosflm; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

(E)-1-(4-Chlorophenyl)-2-[2,2-dichloro-1-(4-fluorophenyl)ethenyl]\ diazene

Crystal data

C14H8Cl3FN2	F(000) = 664
Mr = 329.57	Dx = 1.592 Mg m^−3
Monoclinic, P21/c	Synchrotron radiation, λ = 0.80246 Å
a = 3.8617 (8) Å	Cell parameters from 600 reflections
b = 24.249 (5) Å	θ = 3.3–30.0°
c = 14.724 (3) Å	µ = 0.93 mm^−1
β = 94.30 (3)°	T = 100 K
V = 1374.9 (5) Å^3	Plate, orange
Z = 4	0.20 × 0.10 × 0.02 mm

Data collection

Rayonix SX165 CCD diffractometer	2719 reflections with I > 2σ(I)
/f scan	Rint = 0.115
Absorption correction: multi-scan (Scala; Evans, 2006)	θmax = 30.9°, θmin = 3.3°
Tmin = 0.840, Tmax = 0.970	h = −4→4
20761 measured reflections	k = −30→31
2984 independent reflections	l = −18→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.0557P)^2 + 1.092P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2984 reflections	Δρmax = 0.59 e Å^−3
182 parameters	Δρmin = −0.72 e Å^−3
0 restraints	Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: difference Fourier map	Extinction coefficient: 0.026 (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
Cl1	0.68912 (17)	0.12097 (2)	0.17209 (4)	0.0265 (2)
Cl2	0.48467 (18)	0.22728 (2)	0.10431 (4)	0.0283 (2)
Cl3	−0.18247 (18)	0.50802 (2)	0.35787 (5)	0.0318 (2)
F1	0.5868 (5)	0.06509 (7)	0.58998 (10)	0.0386 (4)
N1	0.3562 (6)	0.25699 (8)	0.28387 (14)	0.0246 (5)
N2	0.2435 (6)	0.27366 (8)	0.35685 (14)	0.0230 (4)
C1	0.4622 (7)	0.20110 (9)	0.28183 (16)	0.0225 (5)
C2	0.5361 (7)	0.18506 (9)	0.19760 (16)	0.0237 (5)
C3	0.4936 (7)	0.16469 (9)	0.36354 (16)	0.0232 (5)
C4	0.6716 (7)	0.18329 (10)	0.44378 (16)	0.0249 (5)
H4	0.7714	0.2191	0.4459	0.030*
C5	0.7036 (7)	0.14978 (10)	0.52038 (16)	0.0283 (6)
H5	0.8242	0.1622	0.5752	0.034*
C6	0.5558 (8)	0.09804 (10)	0.51483 (17)	0.0287 (6)
C7	0.3803 (7)	0.07791 (10)	0.43694 (17)	0.0280 (5)
H7	0.2840	0.0418	0.4352	0.034*
C8	0.3485 (7)	0.11196 (10)	0.36103 (17)	0.0243 (5)
H8	0.2264	0.0992	0.3067	0.029*
C9	0.1482 (7)	0.33066 (9)	0.35229 (16)	0.0225 (5)
C10	0.1990 (7)	0.36475 (10)	0.27784 (16)	0.0251 (5)
H10	0.3012	0.3504	0.2261	0.030*
C11	0.1000 (7)	0.41943 (10)	0.27997 (16)	0.0257 (5)
H11	0.1332	0.4430	0.2298	0.031*
C12	−0.0490 (7)	0.43956 (10)	0.35640 (17)	0.0246 (5)
C13	−0.0997 (7)	0.40658 (10)	0.43064 (17)	0.0255 (5)
H13	−0.2002	0.4212	0.4824	0.031*
C14	−0.0012 (7)	0.35157 (10)	0.42818 (16)	0.0248 (5)
H14	−0.0358	0.3282	0.4784	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0363 (4)	0.0157 (3)	0.0273 (3)	0.0018 (2)	0.0006 (2)	−0.0038 (2)
Cl2	0.0408 (4)	0.0196 (3)	0.0243 (3)	0.0022 (2)	0.0017 (2)	0.0020 (2)
Cl3	0.0384 (4)	0.0125 (3)	0.0442 (4)	0.0020 (2)	0.0011 (3)	0.0002 (2)
F1	0.0622 (12)	0.0241 (8)	0.0290 (8)	0.0040 (8)	−0.0004 (7)	0.0087 (6)
N1	0.0333 (12)	0.0135 (9)	0.0266 (10)	−0.0008 (8)	0.0000 (8)	−0.0019 (7)
N2	0.0292 (11)	0.0128 (9)	0.0269 (10)	0.0004 (8)	0.0008 (8)	−0.0015 (7)
C1	0.0273 (13)	0.0123 (10)	0.0272 (11)	−0.0027 (9)	−0.0017 (9)	−0.0010 (8)
C2	0.0286 (13)	0.0146 (10)	0.0272 (11)	−0.0032 (9)	−0.0019 (9)	−0.0014 (8)
C3	0.0301 (13)	0.0143 (11)	0.0253 (11)	0.0017 (9)	0.0013 (9)	−0.0013 (8)
C4	0.0316 (14)	0.0149 (11)	0.0279 (11)	0.0016 (9)	0.0007 (10)	−0.0005 (9)
C5	0.0361 (15)	0.0214 (12)	0.0267 (11)	0.0039 (10)	−0.0023 (10)	−0.0023 (9)
C6	0.0407 (15)	0.0175 (11)	0.0280 (11)	0.0064 (10)	0.0037 (10)	0.0060 (9)
C7	0.0376 (15)	0.0143 (11)	0.0321 (12)	0.0007 (10)	0.0037 (10)	0.0016 (9)
C8	0.0291 (13)	0.0153 (11)	0.0285 (11)	0.0000 (9)	0.0013 (10)	−0.0017 (9)
C9	0.0288 (13)	0.0112 (10)	0.0269 (11)	0.0003 (9)	−0.0025 (9)	−0.0011 (8)
C10	0.0315 (14)	0.0176 (11)	0.0259 (11)	−0.0001 (9)	−0.0004 (9)	0.0001 (9)
C11	0.0332 (14)	0.0157 (11)	0.0277 (11)	−0.0010 (9)	−0.0020 (10)	0.0022 (9)
C12	0.0286 (13)	0.0132 (11)	0.0312 (12)	−0.0020 (9)	−0.0037 (10)	−0.0005 (9)
C13	0.0302 (13)	0.0165 (11)	0.0292 (11)	−0.0012 (9)	−0.0009 (9)	−0.0037 (9)
C14	0.0319 (14)	0.0175 (11)	0.0243 (11)	−0.0007 (9)	−0.0019 (9)	0.0013 (9)

Geometric parameters (Å, º)

Cl1—C2	1.714 (2)	C6—C7	1.377 (4)
Cl2—C2	1.713 (2)	C7—C8	1.388 (3)
Cl3—C12	1.739 (2)	C7—H7	0.9500
F1—C6	1.363 (3)	C8—H8	0.9500
N1—N2	1.256 (3)	C9—C14	1.391 (3)
N1—C1	1.417 (3)	C9—C10	1.399 (3)
N2—C9	1.431 (3)	C10—C11	1.381 (3)
C1—C2	1.351 (3)	C10—H10	0.9500
C1—C3	1.490 (3)	C11—C12	1.390 (4)
C3—C8	1.395 (3)	C11—H11	0.9500
C3—C4	1.396 (3)	C12—C13	1.380 (3)
C4—C5	1.388 (3)	C13—C14	1.389 (3)
C4—H4	0.9500	C13—H13	0.9500
C5—C6	1.378 (4)	C14—H14	0.9500
C5—H5	0.9500
N2—N1—C1	116.43 (19)	C8—C7—H7	121.0
N1—N2—C9	112.0 (2)	C7—C8—C3	120.9 (2)
C2—C1—N1	112.1 (2)	C7—C8—H8	119.6
C2—C1—C3	124.1 (2)	C3—C8—H8	119.6
N1—C1—C3	123.8 (2)	C14—C9—C10	120.4 (2)
C1—C2—Cl2	122.99 (19)	C14—C9—N2	115.8 (2)
C1—C2—Cl1	124.22 (18)	C10—C9—N2	123.9 (2)
Cl2—C2—Cl1	112.79 (14)	C11—C10—C9	119.6 (2)
C8—C3—C4	119.3 (2)	C11—C10—H10	120.2
C8—C3—C1	120.9 (2)	C9—C10—H10	120.2
C4—C3—C1	119.8 (2)	C10—C11—C12	119.2 (2)
C5—C4—C3	120.4 (2)	C10—C11—H11	120.4
C5—C4—H4	119.8	C12—C11—H11	120.4
C3—C4—H4	119.8	C13—C12—C11	122.0 (2)
C6—C5—C4	118.3 (2)	C13—C12—Cl3	118.9 (2)
C6—C5—H5	120.9	C11—C12—Cl3	119.10 (18)
C4—C5—H5	120.9	C12—C13—C14	118.7 (2)
F1—C6—C7	118.4 (2)	C12—C13—H13	120.6
F1—C6—C5	118.3 (2)	C14—C13—H13	120.6
C7—C6—C5	123.2 (2)	C13—C14—C9	120.1 (2)
C6—C7—C8	117.9 (2)	C13—C14—H14	119.9
C6—C7—H7	121.0	C9—C14—H14	119.9
C1—N1—N2—C9	179.2 (2)	C5—C6—C7—C8	−0.8 (4)
N2—N1—C1—C2	171.9 (2)	C6—C7—C8—C3	0.7 (4)
N2—N1—C1—C3	−9.0 (4)	C4—C3—C8—C7	−0.3 (4)
N1—C1—C2—Cl2	−3.0 (3)	C1—C3—C8—C7	179.5 (2)
C3—C1—C2—Cl2	177.94 (19)	N1—N2—C9—C14	175.9 (2)
N1—C1—C2—Cl1	177.14 (18)	N1—N2—C9—C10	−4.5 (4)
C3—C1—C2—Cl1	−1.9 (4)	C14—C9—C10—C11	0.0 (4)
C2—C1—C3—C8	−49.2 (4)	N2—C9—C10—C11	−179.6 (2)
N1—C1—C3—C8	131.8 (3)	C9—C10—C11—C12	0.0 (4)
C2—C1—C3—C4	130.5 (3)	C10—C11—C12—C13	0.3 (4)
N1—C1—C3—C4	−48.4 (4)	C10—C11—C12—Cl3	−178.57 (19)
C8—C3—C4—C5	−0.1 (4)	C11—C12—C13—C14	−0.6 (4)
C1—C3—C4—C5	−179.9 (2)	Cl3—C12—C13—C14	178.31 (19)
C3—C4—C5—C6	0.0 (4)	C12—C13—C14—C9	0.5 (4)
C4—C5—C6—F1	−180.0 (2)	C10—C9—C14—C13	−0.2 (4)
C4—C5—C6—C7	0.4 (4)	N2—C9—C14—C13	179.4 (2)
F1—C6—C7—C8	179.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cl1^i	0.95	2.81	3.634 (3)	146

Symmetry code: (i) x−1, y, z.