Crystal structure and Hirshfeld surface analysis of (E)-4-{2,2-di­chloro-1-[(3,5-di­methyl­phen­yl)diazen­yl]ethen­yl}-N,N-di­methyl­aniline

In the crystal of the title compound, the mol­ecules are associated into inversion dimers via short Cl...Cl halogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.125
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT703_ALERT_1_A Torsion Calc  173.28(17), Rep -173.27(17), Dev..      79.12 Sigma
              C16 -C7  -N2  -N1     1.555   1.555   1.555   1.555  #   34 Check

Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C11 Check
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.143 Report
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         80 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....         52 Note

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT434_ALERT_2_G Short Inter HL..HL Contact Cl1      ..Cl1              3.38 Ang.
                                                2-x,1-y,2-z  =      2_767 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          5 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Info

   1 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 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
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 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: APEX3 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

(E)-4-{2,2-Dichloro-1-[(3,5-dimethylphenyl)diazenyl]ethenyl}-N,N-dimethylaniline

Crystal data

C18H19Cl2N3	Z = 2
Mr = 348.26	F(000) = 364
Triclinic, P1	Dx = 1.293 Mg m^−3
a = 8.1035 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1965 (5) Å	Cell parameters from 7784 reflections
c = 12.3665 (7) Å	θ = 2.3–25.7°
α = 102.421 (2)°	µ = 0.37 mm^−1
β = 95.880 (2)°	T = 296 K
γ = 91.105 (2)°	Plate, orange
V = 894.48 (8) Å^3	0.28 × 0.22 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer	2786 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.039
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 25.8°, θmin = 2.3°
Tmin = 0.897, Tmax = 0.924	h = −9→9
13675 measured reflections	k = −10→11
3339 independent reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0539P)^2 + 0.3599P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
3339 reflections	Δρmax = 0.30 e Å^−3
212 parameters	Δρmin = −0.21 e Å^−3
0 restraints

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	0.4932 (2)	0.5319 (2)	0.78212 (16)	0.0507 (4)
C2	0.3377 (3)	0.5251 (2)	0.72287 (17)	0.0572 (5)
H2A	0.313279	0.592879	0.678105	0.069*
C3	0.2180 (2)	0.4186 (2)	0.72940 (19)	0.0586 (5)
C4	0.2585 (2)	0.3198 (2)	0.79718 (18)	0.0578 (5)
H4A	0.179261	0.247628	0.801995	0.069*
C5	0.4136 (2)	0.3245 (2)	0.85843 (16)	0.0528 (4)
C6	0.5313 (2)	0.4323 (2)	0.85097 (16)	0.0515 (4)
H6A	0.635267	0.438287	0.891630	0.062*
C7	0.8563 (2)	0.7644 (2)	0.81327 (15)	0.0486 (4)
C8	0.8188 (2)	0.8616 (2)	0.73299 (15)	0.0470 (4)
C9	0.7799 (3)	1.0079 (2)	0.76813 (17)	0.0624 (5)
H9A	0.780539	1.047283	0.844019	0.075*
C10	0.7401 (3)	1.0978 (2)	0.69421 (18)	0.0663 (6)
H10A	0.713687	1.195886	0.721428	0.080*
C11	0.7385 (2)	1.0455 (2)	0.58013 (16)	0.0530 (4)
C12	0.7818 (4)	0.8986 (3)	0.54516 (18)	0.0731 (7)
H12A	0.785747	0.859575	0.469609	0.088*
C13	0.8188 (3)	0.8099 (2)	0.61981 (18)	0.0705 (6)
H13A	0.844835	0.711493	0.593078	0.085*
C14	0.0476 (3)	0.4121 (3)	0.6668 (3)	0.0815 (7)
H14A	0.015539	0.310513	0.631791	0.122*
H14B	0.049299	0.470111	0.610925	0.122*
H14C	−0.030567	0.451581	0.717658	0.122*
C15	0.4523 (3)	0.2146 (3)	0.9306 (2)	0.0681 (6)
H15A	0.553126	0.246587	0.978497	0.102*
H15B	0.465759	0.118284	0.884317	0.102*
H15C	0.362933	0.208661	0.974908	0.102*
C16	0.9971 (2)	0.7786 (2)	0.88186 (16)	0.0520 (4)
C17	0.6238 (4)	1.2751 (3)	0.5403 (2)	0.0806 (7)
H17A	0.556425	1.271764	0.599308	0.121*
H17B	0.556809	1.299516	0.478616	0.121*
H17C	0.711966	1.349476	0.566573	0.121*
C18	0.6996 (5)	1.0776 (3)	0.3882 (2)	0.0944 (9)
H18A	0.639013	0.983527	0.364268	0.142*
H18B	0.813161	1.065188	0.373532	0.142*
H18C	0.651020	1.147779	0.348239	0.142*
Cl1	1.04137 (8)	0.67088 (7)	0.97728 (5)	0.0734 (2)
Cl2	1.15092 (7)	0.90973 (7)	0.88372 (5)	0.0707 (2)
N1	0.6056 (2)	0.64606 (18)	0.76759 (14)	0.0552 (4)
N2	0.7438 (2)	0.64937 (17)	0.82395 (13)	0.0523 (4)
N3	0.6932 (3)	1.1321 (2)	0.50518 (15)	0.0745 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0541 (10)	0.0443 (9)	0.0535 (10)	−0.0068 (8)	0.0080 (8)	0.0098 (8)
C2	0.0576 (11)	0.0520 (11)	0.0617 (12)	0.0014 (8)	0.0037 (9)	0.0127 (9)
C3	0.0487 (10)	0.0522 (11)	0.0701 (12)	−0.0004 (8)	0.0069 (9)	0.0031 (9)
C4	0.0515 (11)	0.0497 (11)	0.0695 (13)	−0.0095 (8)	0.0145 (9)	0.0044 (9)
C5	0.0587 (11)	0.0445 (10)	0.0555 (11)	−0.0058 (8)	0.0135 (9)	0.0085 (8)
C6	0.0522 (10)	0.0489 (10)	0.0524 (10)	−0.0075 (8)	0.0047 (8)	0.0104 (8)
C7	0.0573 (10)	0.0433 (9)	0.0470 (9)	−0.0069 (8)	0.0098 (8)	0.0127 (7)
C8	0.0526 (10)	0.0438 (9)	0.0462 (9)	−0.0061 (7)	0.0053 (7)	0.0139 (7)
C9	0.0852 (15)	0.0571 (12)	0.0450 (10)	0.0091 (10)	0.0075 (10)	0.0105 (9)
C10	0.0933 (16)	0.0507 (11)	0.0555 (11)	0.0152 (11)	0.0078 (11)	0.0116 (9)
C11	0.0605 (11)	0.0506 (10)	0.0509 (10)	0.0002 (8)	0.0071 (8)	0.0173 (8)
C12	0.116 (2)	0.0619 (13)	0.0454 (11)	0.0188 (13)	0.0177 (11)	0.0156 (9)
C13	0.1110 (19)	0.0516 (11)	0.0516 (11)	0.0172 (12)	0.0162 (11)	0.0124 (9)
C14	0.0548 (13)	0.0765 (16)	0.107 (2)	0.0020 (11)	−0.0048 (12)	0.0125 (14)
C15	0.0748 (14)	0.0611 (13)	0.0729 (14)	−0.0112 (10)	0.0133 (11)	0.0237 (11)
C16	0.0617 (11)	0.0470 (10)	0.0501 (10)	−0.0114 (8)	0.0049 (8)	0.0187 (8)
C17	0.0918 (18)	0.0726 (15)	0.0815 (16)	0.0185 (13)	−0.0053 (13)	0.0312 (13)
C18	0.147 (3)	0.0867 (18)	0.0594 (14)	0.0169 (18)	0.0137 (15)	0.0345 (13)
Cl1	0.0839 (4)	0.0724 (4)	0.0705 (4)	−0.0174 (3)	−0.0110 (3)	0.0408 (3)
Cl2	0.0679 (4)	0.0737 (4)	0.0743 (4)	−0.0273 (3)	−0.0064 (3)	0.0340 (3)
N1	0.0584 (10)	0.0498 (9)	0.0589 (9)	−0.0091 (7)	0.0039 (8)	0.0170 (7)
N2	0.0568 (9)	0.0478 (8)	0.0543 (9)	−0.0093 (7)	0.0075 (7)	0.0161 (7)
N3	0.1083 (16)	0.0659 (11)	0.0564 (10)	0.0201 (11)	0.0110 (10)	0.0269 (9)

Geometric parameters (Å, º)

C1—C2	1.384 (3)	C11—C12	1.391 (3)
C1—C6	1.397 (3)	C12—C13	1.373 (3)
C1—N1	1.429 (2)	C12—H12A	0.9300
C2—C3	1.385 (3)	C13—H13A	0.9300
C2—H2A	0.9300	C14—H14A	0.9600
C3—C4	1.385 (3)	C14—H14B	0.9600
C3—C14	1.506 (3)	C14—H14C	0.9600
C4—C5	1.394 (3)	C15—H15A	0.9600
C4—H4A	0.9300	C15—H15B	0.9600
C5—C6	1.387 (3)	C15—H15C	0.9600
C5—C15	1.503 (3)	C16—Cl1	1.7123 (19)
C6—H6A	0.9300	C16—Cl2	1.7129 (18)
C7—C16	1.336 (3)	C17—N3	1.438 (3)
C7—N2	1.420 (2)	C17—H17A	0.9600
C7—C8	1.485 (2)	C17—H17B	0.9600
C8—C9	1.375 (3)	C17—H17C	0.9600
C8—C13	1.378 (3)	C18—N3	1.433 (3)
C9—C10	1.378 (3)	C18—H18A	0.9600
C9—H9A	0.9300	C18—H18B	0.9600
C10—C11	1.388 (3)	C18—H18C	0.9600
C10—H10A	0.9300	N1—N2	1.254 (2)
C11—N3	1.374 (3)
C2—C1—C6	120.38 (17)	C12—C13—C8	122.3 (2)
C2—C1—N1	115.34 (17)	C12—C13—H13A	118.9
C6—C1—N1	124.28 (17)	C8—C13—H13A	118.9
C1—C2—C3	120.85 (19)	C3—C14—H14A	109.5
C1—C2—H2A	119.6	C3—C14—H14B	109.5
C3—C2—H2A	119.6	H14A—C14—H14B	109.5
C4—C3—C2	118.00 (19)	C3—C14—H14C	109.5
C4—C3—C14	120.8 (2)	H14A—C14—H14C	109.5
C2—C3—C14	121.2 (2)	H14B—C14—H14C	109.5
C3—C4—C5	122.48 (18)	C5—C15—H15A	109.5
C3—C4—H4A	118.8	C5—C15—H15B	109.5
C5—C4—H4A	118.8	H15A—C15—H15B	109.5
C6—C5—C4	118.55 (18)	C5—C15—H15C	109.5
C6—C5—C15	120.77 (19)	H15A—C15—H15C	109.5
C4—C5—C15	120.67 (18)	H15B—C15—H15C	109.5
C5—C6—C1	119.72 (18)	C7—C16—Cl1	124.05 (14)
C5—C6—H6A	120.1	C7—C16—Cl2	122.70 (14)
C1—C6—H6A	120.1	Cl1—C16—Cl2	113.24 (11)
C16—C7—N2	114.49 (16)	N3—C17—H17A	109.5
C16—C7—C8	123.12 (16)	N3—C17—H17B	109.5
N2—C7—C8	122.39 (16)	H17A—C17—H17B	109.5
C9—C8—C13	116.53 (18)	N3—C17—H17C	109.5
C9—C8—C7	121.42 (17)	H17A—C17—H17C	109.5
C13—C8—C7	122.04 (17)	H17B—C17—H17C	109.5
C8—C9—C10	121.94 (18)	N3—C18—H18A	109.5
C8—C9—H9A	119.0	N3—C18—H18B	109.5
C10—C9—H9A	119.0	H18A—C18—H18B	109.5
C9—C10—C11	121.60 (19)	N3—C18—H18C	109.5
C9—C10—H10A	119.2	H18A—C18—H18C	109.5
C11—C10—H10A	119.2	H18B—C18—H18C	109.5
N3—C11—C10	122.27 (19)	N2—N1—C1	113.12 (16)
N3—C11—C12	121.46 (18)	N1—N2—C7	114.22 (16)
C10—C11—C12	116.26 (18)	C11—N3—C18	121.15 (19)
C13—C12—C11	121.38 (19)	C11—N3—C17	121.07 (19)
C13—C12—H12A	119.3	C18—N3—C17	117.6 (2)
C11—C12—H12A	119.3
C6—C1—C2—C3	−0.9 (3)	C9—C10—C11—C12	−1.0 (4)
N1—C1—C2—C3	179.58 (18)	N3—C11—C12—C13	−176.6 (2)
C1—C2—C3—C4	0.2 (3)	C10—C11—C12—C13	1.9 (4)
C1—C2—C3—C14	178.9 (2)	C11—C12—C13—C8	−1.4 (4)
C2—C3—C4—C5	0.2 (3)	C9—C8—C13—C12	−0.2 (4)
C14—C3—C4—C5	−178.5 (2)	C7—C8—C13—C12	179.0 (2)
C3—C4—C5—C6	0.0 (3)	N2—C7—C16—Cl1	−0.9 (3)
C3—C4—C5—C15	−179.74 (19)	C8—C7—C16—Cl1	178.48 (14)
C4—C5—C6—C1	−0.6 (3)	N2—C7—C16—Cl2	179.97 (14)
C15—C5—C6—C1	179.08 (18)	C8—C7—C16—Cl2	−0.6 (3)
C2—C1—C6—C5	1.1 (3)	C2—C1—N1—N2	179.06 (17)
N1—C1—C6—C5	−179.40 (17)	C6—C1—N1—N2	−0.5 (3)
C16—C7—C8—C9	−72.4 (3)	C1—N1—N2—C7	−178.40 (15)
N2—C7—C8—C9	107.0 (2)	C16—C7—N2—N1	−173.27 (17)
C16—C7—C8—C13	108.5 (3)	C8—C7—N2—N1	−6.1 (3)
N2—C7—C8—C13	−72.1 (3)	C10—C11—N3—C18	177.2 (3)
C13—C8—C9—C10	1.1 (3)	C12—C11—N3—C18	−4.4 (4)
C7—C8—C9—C10	−178.0 (2)	C10—C11—N3—C17	−8.3 (4)
C8—C9—C10—C11	−0.5 (4)	C12—C11—N3—C17	170.1 (3)
C9—C10—C11—N3	177.5 (2)