Crystal structure and Hirshfeld surface analysis of (E)-4-{[2,2-di­chloro-1-(4-meth­oxy­phen­yl)ethen­yl]diazen­yl}benzo­nitrile

In the crystal structure, the mol­ecules are linked into layers parallel to the (020) plane by C—H...O contacts and face-to-face π–π stacking inter­actions between symmetry-related aromatic rings along the a-axis direction.

Key indicators

• Single-crystal synchrotron study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.123
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.004 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         13 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          7 Note

Alert level G
ABSMU01_ALERT_1_G  Calculation of _exptl_absorpt_correction_mu
                not performed for this radiation type.
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT092_ALERT_4_G Check: Wavelength Given is not Cu,Ga,Mo,Ag,In Ka    0.80246 Ang.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          8 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 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
   6 ALERT level G = General information/check it is not something unexpected

   2 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: Marccd (Doyle, 2011); cell refinement: iMosflm (Battye et al., 2011); data reduction: iMosflm (Battye et al., 2011); program(s) used to solve structure: SHELXLS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

(E)-4-{[2,2-Dichloro-1-(4-methoxyphenyl)ethenyl]diazenyl}benzonitrile

Crystal data

C16H11Cl2N3O	F(000) = 680
Mr = 332.18	Dx = 1.512 Mg m^−3
Monoclinic, P21/c	Synchrotron radiation, λ = 0.80246 Å
a = 3.9117 (8) Å	Cell parameters from 600 reflections
b = 25.109 (5) Å	θ = 1.8–30.0°
c = 14.968 (3) Å	µ = 0.63 mm^−1
β = 97.07 (3)°	T = 100 K
V = 1459.0 (5) Å^3	Needle, orange
Z = 4	0.25 × 0.05 × 0.03 mm

Data collection

Rayonix SX165 CCD diffractometer	2978 reflections with I > 2σ(I)
/f scan	Rint = 0.068
Absorption correction: multi-scan (Scala; Evans, 2006)	θmax = 30.9°, θmin = 1.8°
Tmin = 0.850, Tmax = 0.975	h = −4→4
22750 measured reflections	k = −32→32
3144 independent reflections	l = −19→19

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.045	w = 1/[σ^2(Fo^2) + (0.066P)^2 + 0.9448P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.123	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.30 e Å^−3
3144 reflections	Δρmin = −0.46 e Å^−3
201 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.049 (5)

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
C1	0.4566 (5)	0.66476 (7)	0.67302 (12)	0.0215 (4)
H1	0.463381	0.687885	0.723440	0.026*
C2	0.3294 (5)	0.61359 (7)	0.67752 (13)	0.0221 (4)
H2	0.244963	0.601450	0.730780	0.026*
C3	0.3261 (5)	0.57981 (7)	0.60312 (13)	0.0215 (4)
C4	0.4409 (5)	0.59720 (7)	0.52351 (12)	0.0228 (4)
H4	0.436434	0.574023	0.473208	0.027*
C5	0.5621 (5)	0.64912 (7)	0.51906 (12)	0.0214 (4)
H5	0.636172	0.661965	0.464913	0.026*
C6	0.5748 (5)	0.68213 (7)	0.59378 (12)	0.0197 (4)
C7	0.9517 (5)	0.80678 (7)	0.65882 (12)	0.0199 (4)
C8	1.0851 (5)	0.82299 (7)	0.74254 (13)	0.0218 (4)
C9	0.9344 (5)	0.84019 (7)	0.57700 (12)	0.0199 (4)
C10	1.0545 (5)	0.82125 (7)	0.49838 (13)	0.0210 (4)
H10	1.155098	0.786823	0.498109	0.025*
C11	1.0283 (5)	0.85197 (7)	0.42152 (12)	0.0213 (4)
H11	1.108147	0.838403	0.368576	0.026*
C12	0.8849 (5)	0.90295 (7)	0.42105 (12)	0.0198 (4)
C13	0.7626 (5)	0.92238 (7)	0.49813 (13)	0.0208 (4)
H13	0.662374	0.956840	0.498230	0.025*
C14	0.7886 (5)	0.89082 (7)	0.57518 (13)	0.0210 (4)
H14	0.704725	0.904154	0.627752	0.025*
C15	0.1992 (5)	0.52632 (8)	0.61044 (13)	0.0249 (4)
C16	0.7123 (5)	0.98149 (7)	0.33590 (13)	0.0246 (4)
H16A	0.731494	0.997143	0.276745	0.037*
H16B	0.823240	1.005003	0.383095	0.037*
H16C	0.468596	0.977180	0.343527	0.037*
N1	0.7074 (4)	0.73473 (6)	0.58427 (10)	0.0207 (3)
N2	0.8218 (4)	0.75417 (6)	0.65946 (10)	0.0212 (3)
N3	0.1007 (5)	0.48385 (7)	0.61986 (13)	0.0345 (4)
O1	0.8781 (4)	0.93062 (5)	0.34222 (9)	0.0233 (3)
Cl1	1.07739 (13)	0.78390 (2)	0.83659 (3)	0.02703 (18)
Cl2	1.27416 (13)	0.88356 (2)	0.76669 (3)	0.02496 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0237 (9)	0.0195 (9)	0.0207 (9)	0.0005 (7)	−0.0001 (7)	0.0001 (7)
C2	0.0246 (9)	0.0192 (9)	0.0220 (9)	0.0002 (7)	0.0009 (7)	0.0028 (7)
C3	0.0234 (9)	0.0166 (8)	0.0234 (9)	−0.0005 (7)	−0.0012 (7)	0.0016 (7)
C4	0.0285 (10)	0.0197 (9)	0.0193 (9)	−0.0018 (7)	−0.0009 (7)	−0.0006 (7)
C5	0.0242 (9)	0.0195 (8)	0.0193 (8)	−0.0005 (7)	−0.0021 (7)	0.0024 (7)
C6	0.0207 (9)	0.0154 (8)	0.0218 (9)	0.0007 (7)	−0.0020 (7)	0.0027 (6)
C7	0.0223 (9)	0.0159 (8)	0.0211 (9)	0.0008 (7)	0.0016 (7)	−0.0007 (6)
C8	0.0257 (9)	0.0173 (8)	0.0223 (9)	0.0005 (7)	0.0025 (7)	−0.0010 (7)
C9	0.0215 (9)	0.0167 (8)	0.0207 (9)	−0.0021 (7)	−0.0003 (7)	−0.0006 (6)
C10	0.0244 (9)	0.0159 (8)	0.0221 (9)	0.0002 (7)	0.0000 (7)	−0.0026 (7)
C11	0.0244 (9)	0.0181 (8)	0.0211 (9)	−0.0005 (7)	0.0016 (7)	−0.0021 (7)
C12	0.0221 (9)	0.0186 (8)	0.0179 (8)	−0.0029 (7)	−0.0007 (7)	0.0012 (6)
C13	0.0237 (9)	0.0150 (8)	0.0231 (9)	−0.0004 (7)	0.0006 (7)	−0.0003 (7)
C14	0.0247 (9)	0.0178 (8)	0.0201 (9)	−0.0004 (7)	0.0017 (7)	−0.0018 (6)
C15	0.0294 (10)	0.0231 (10)	0.0217 (9)	−0.0028 (8)	0.0011 (7)	−0.0002 (7)
C16	0.0290 (10)	0.0182 (9)	0.0254 (10)	0.0013 (7)	−0.0015 (7)	0.0030 (7)
N1	0.0225 (8)	0.0161 (7)	0.0227 (8)	0.0004 (6)	−0.0004 (6)	0.0013 (6)
N2	0.0251 (8)	0.0164 (7)	0.0212 (8)	−0.0003 (6)	−0.0007 (6)	−0.0006 (6)
N3	0.0490 (12)	0.0242 (9)	0.0304 (9)	−0.0092 (8)	0.0046 (8)	−0.0008 (7)
O1	0.0307 (7)	0.0186 (6)	0.0203 (7)	0.0020 (5)	0.0018 (5)	0.0023 (5)
Cl1	0.0386 (3)	0.0223 (3)	0.0191 (3)	−0.00365 (18)	−0.00068 (19)	0.00226 (16)
Cl2	0.0343 (3)	0.0185 (3)	0.0213 (3)	−0.00454 (17)	0.00074 (18)	−0.00278 (15)

Geometric parameters (Å, º)

C1—C2	1.382 (3)	C9—C14	1.392 (2)
C1—C6	1.395 (3)	C9—C10	1.403 (3)
C1—H1	0.9500	C10—C11	1.378 (3)
C2—C3	1.399 (3)	C10—H10	0.9500
C2—H2	0.9500	C11—C12	1.397 (3)
C3—C4	1.394 (3)	C11—H11	0.9500
C3—C15	1.441 (3)	C12—O1	1.367 (2)
C4—C5	1.392 (3)	C12—C13	1.391 (3)
C4—H4	0.9500	C13—C14	1.393 (3)
C5—C6	1.388 (3)	C13—H13	0.9500
C5—H5	0.9500	C14—H14	0.9500
C6—N1	1.433 (2)	C15—N3	1.149 (3)
C7—C8	1.359 (3)	C16—O1	1.430 (2)
C7—N2	1.416 (2)	C16—H16A	0.9800
C7—C9	1.479 (2)	C16—H16B	0.9800
C8—Cl2	1.7103 (19)	C16—H16C	0.9800
C8—Cl1	1.7196 (19)	N1—N2	1.257 (2)
C2—C1—C6	119.40 (17)	C10—C9—C7	121.08 (16)
C2—C1—H1	120.3	C11—C10—C9	120.81 (17)
C6—C1—H1	120.3	C11—C10—H10	119.6
C1—C2—C3	119.55 (18)	C9—C10—H10	119.6
C1—C2—H2	120.2	C10—C11—C12	120.36 (17)
C3—C2—H2	120.2	C10—C11—H11	119.8
C4—C3—C2	121.20 (17)	C12—C11—H11	119.8
C4—C3—C15	120.48 (17)	O1—C12—C13	124.46 (17)
C2—C3—C15	118.32 (17)	O1—C12—C11	115.79 (16)
C5—C4—C3	118.80 (17)	C13—C12—C11	119.74 (17)
C5—C4—H4	120.6	C12—C13—C14	119.34 (17)
C3—C4—H4	120.6	C12—C13—H13	120.3
C6—C5—C4	119.96 (17)	C14—C13—H13	120.3
C6—C5—H5	120.0	C9—C14—C13	121.59 (17)
C4—C5—H5	120.0	C9—C14—H14	119.2
C5—C6—C1	121.04 (17)	C13—C14—H14	119.2
C5—C6—N1	116.61 (16)	N3—C15—C3	177.3 (2)
C1—C6—N1	122.33 (16)	O1—C16—H16A	109.5
C8—C7—N2	111.75 (16)	O1—C16—H16B	109.5
C8—C7—C9	124.52 (17)	H16A—C16—H16B	109.5
N2—C7—C9	123.71 (15)	O1—C16—H16C	109.5
C7—C8—Cl2	124.62 (15)	H16A—C16—H16C	109.5
C7—C8—Cl1	122.71 (15)	H16B—C16—H16C	109.5
Cl2—C8—Cl1	112.66 (11)	N2—N1—C6	111.24 (15)
C14—C9—C10	118.16 (17)	N1—N2—C7	116.40 (15)
C14—C9—C7	120.73 (17)	C12—O1—C16	118.13 (15)
C6—C1—C2—C3	0.9 (3)	C14—C9—C10—C11	0.0 (3)
C1—C2—C3—C4	−1.6 (3)	C7—C9—C10—C11	178.04 (17)
C1—C2—C3—C15	178.65 (18)	C9—C10—C11—C12	0.8 (3)
C2—C3—C4—C5	0.3 (3)	C10—C11—C12—O1	178.52 (17)
C15—C3—C4—C5	−179.91 (18)	C10—C11—C12—C13	−1.1 (3)
C3—C4—C5—C6	1.5 (3)	O1—C12—C13—C14	−178.90 (17)
C4—C5—C6—C1	−2.2 (3)	C11—C12—C13—C14	0.7 (3)
C4—C5—C6—N1	179.12 (16)	C10—C9—C14—C13	−0.4 (3)
C2—C1—C6—C5	0.9 (3)	C7—C9—C14—C13	−178.47 (17)
C2—C1—C6—N1	179.54 (17)	C12—C13—C14—C9	0.0 (3)
N2—C7—C8—Cl2	178.27 (14)	C5—C6—N1—N2	−156.50 (17)
C9—C7—C8—Cl2	−3.3 (3)	C1—C6—N1—N2	24.8 (2)
N2—C7—C8—Cl1	−2.2 (2)	C6—N1—N2—C7	−178.37 (15)
C9—C7—C8—Cl1	176.26 (14)	C8—C7—N2—N1	−176.77 (17)
C8—C7—C9—C14	−52.1 (3)	C9—C7—N2—N1	4.8 (3)
N2—C7—C9—C14	126.2 (2)	C13—C12—O1—C16	−4.7 (3)
C8—C7—C9—C10	129.9 (2)	C11—C12—O1—C16	175.67 (16)
N2—C7—C9—C10	−51.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1^i	0.95	2.47	3.391 (2)	165
C16—H16C···O1^ii	0.98	2.59	3.516 (3)	158

Symmetry codes: (i) x−1, −y+3/2, z+1/2; (ii) x−1, y, z.