Crystal structures and Hirshfeld surface analyses of (E)-1-[1-(4-tert-butyl­phen­yl)-2,2-di­chloro­ethen­yl]-2-phenyl­diazene, (E)-1-[1-(4-tert-butyl­phen­yl)-2,2-di­chloro­ethen­yl]-2-(4-methyl­phen­yl)diazene, (E)-1-[1-(4-tert-butyl­phen­yl)-2,2-di­chloro­ethen­yl]-2-(4-meth­oxy­phen­yl)diazene and (E)-1-[1-(4-tert-butyl­phen­yl)-2,2-di­chloro­ethen­yl]-2-(3-methyl­phen­yl)diazene

Maharramov, A.; Shikhaliyev, N.Q.; Qajar, A.; Atakishiyeva, G.T.; Niyazova, A.; Khrustalev, V.N.; Akkurt, M.; Yıldırım, S. Ö.; Bhattarai, A.

doi:10.1107/S205698902300511X

Crystal structures and Hirshfeld surface analyses of (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-phenyldiazene, (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(4-methylphenyl)diazene, (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(4-methoxyphenyl)diazene and (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(3-methylphenyl)diazene

A. Maharramov, N. Q. Shikhaliyev, A. Qajar, G. T. Atakishiyeva, A. Niyazova, V. N. Khrustalev, M. Akkurt, S. Ö. Yıldırım and A. Bhattarai

C—H

π and C—Cl

π interactions are the most important intermolecular interactions in the crystal structures of the title compounds.

Keywords: crystal structure; azo compounds; C—H

π and C—Cl

π interactions; Hirshfeld surface analysis.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S205698902300511X/wm5684sup1.cif Contains datablocks I, II, III, IV, global
	Structure factor file (CIF format) https://doi.org/10.1107/S205698902300511X/wm5684Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S205698902300511X/wm5684IIsup3.hkl Contains datablock II
	Structure factor file (CIF format) https://doi.org/10.1107/S205698902300511X/wm5684IIIsup4.hkl Contains datablock III
	Structure factor file (CIF format) https://doi.org/10.1107/S205698902300511X/wm5684IVsup5.hkl Contains datablock IV

CCDC references: 2268431; 2268430; 2268429; 2268428

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.038
wR factor = 0.105
Data-to-parameter ratio = 17.5

Structure: II

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.033
wR factor = 0.090
Data-to-parameter ratio = 17.9

Structure: III

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.043
wR factor = 0.118
Data-to-parameter ratio = 17.4

Structure: IV

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.058
wR factor = 0.171
Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT128_ALERT_4_G Alternate Setting for Input Space Group     C2/c       I2/c Note
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         26 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: II


Alert level G
PLAT128_ALERT_4_G Alternate Setting for Input Space Group     C2/c       I2/a Note
PLAT142_ALERT_4_G s.u. on b - Axis Small or Missing ..............    0.00005 Ang.
PLAT152_ALERT_1_G The Supplied and Calc. Volume s.u. Differ by ...          2 Units
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         13 Note
PLAT965_ALERT_2_G The SHELXL WEIGHT Optimisation has not Converged     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         20 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 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
   0 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: III



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT143_ALERT_4_G s.u. on c - Axis Small or Missing ..............    0.00010 Ang.
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         51 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         12 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: IV


Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          8 Report
PLAT975_ALERT_2_C Check Calcd Resid. Dens.  0.98Ang From N1      .       0.43 eA-3

Alert level G
PLAT153_ALERT_1_G The s.u.'s on the Cell Axes   are Equal ..(Note)     0.0002 Ang.
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         83 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 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

   3 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
   1 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

Computing details top

For all structures, data collection: CrysAlis PRO (Rigaku OD, 2021); cell refinement: CrysAlis PRO (Rigaku OD, 2021); data reduction: CrysAlis PRO (Rigaku OD, 2021); program(s) used to solve structure: SHELXT2016/6 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

(E)-1-[1-(4-tert-Butylphenyl)-2,2-dichloroethenyl]-2-phenyldiazene (I) top

Crystal data top

C₁₈H₁₈Cl₂N₂	F(000) = 1392
M_r = 333.24	D_x = 1.324 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
a = 31.7847 (8) Å	Cell parameters from 12999 reflections
b = 6.0289 (1) Å	θ = 3.7–77.3°
c = 23.7220 (6) Å	µ = 3.46 mm⁻¹
β = 132.669 (4)°	T = 100 K
V = 3342.4 (2) Å³	Prism, red
Z = 8	0.23 × 0.18 × 0.15 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	3242 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube	R_int = 0.074
φ and ω scans	θ_max = 77.7°, θ_min = 3.7°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021)	h = −40→33
T_min = 0.339, T_max = 0.580	k = −7→7
25151 measured reflections	l = −30→30
3543 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.105	w = 1/[σ²(F_o²) + (0.0617P)² + 1.5568P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
3543 reflections	Δρ_max = 0.34 e Å⁻³
202 parameters	Δρ_min = −0.35 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.41113 (6)	0.3707 (3)	0.34806 (7)	0.0190 (3)
C2	0.44632 (6)	0.2439 (3)	0.34891 (8)	0.0202 (3)
C3	0.40396 (6)	0.3436 (2)	0.40351 (8)	0.0181 (3)
C4	0.42175 (6)	0.5130 (3)	0.45571 (8)	0.0209 (3)
H4	0.439678	0.641238	0.456824	0.025*
C5	0.41349 (6)	0.4962 (2)	0.50612 (8)	0.0202 (3)
H5	0.426029	0.613327	0.541285	0.024*
C6	0.38719 (6)	0.3110 (2)	0.50615 (7)	0.0174 (3)
C7	0.37085 (6)	0.1406 (3)	0.45491 (8)	0.0202 (3)
H7	0.353829	0.010531	0.454639	0.024*
C8	0.37887 (6)	0.1563 (3)	0.40417 (8)	0.0202 (3)
H8	0.367082	0.037981	0.369712	0.024*
C9	0.37725 (6)	0.2913 (2)	0.56103 (8)	0.0190 (3)
C10	0.37583 (8)	0.5188 (3)	0.58853 (10)	0.0298 (4)
H10A	0.413067	0.591510	0.617926	0.045*
H10B	0.367473	0.499800	0.621133	0.045*
H10C	0.346043	0.610581	0.544116	0.045*
C11	0.32022 (7)	0.1755 (3)	0.52144 (9)	0.0276 (3)
H11A	0.289387	0.251751	0.473242	0.041*
H11B	0.312533	0.179721	0.555056	0.041*
H11C	0.322279	0.020866	0.510718	0.041*
C12	0.42652 (7)	0.1554 (3)	0.63116 (9)	0.0290 (4)
H12A	0.427998	0.009439	0.614365	0.044*
H12B	0.420195	0.136703	0.665981	0.044*
H12C	0.462777	0.233242	0.657860	0.044*
C13	0.31598 (6)	0.8111 (3)	0.23028 (8)	0.0190 (3)
C14	0.33920 (6)	0.9139 (3)	0.20375 (8)	0.0223 (3)
H14	0.373214	0.858034	0.217910	0.027*
C15	0.31215 (7)	1.0977 (3)	0.15666 (9)	0.0263 (3)
H15	0.327976	1.169410	0.138947	0.032*
C16	0.26201 (7)	1.1785 (3)	0.13505 (8)	0.0258 (3)
H16	0.243926	1.305662	0.103079	0.031*
C17	0.23826 (6)	1.0734 (3)	0.16015 (8)	0.0260 (3)
H17	0.203476	1.126355	0.144314	0.031*
C18	0.26553 (6)	0.8909 (3)	0.20839 (8)	0.0231 (3)
H18	0.249845	0.820563	0.226471	0.028*
Cl1	0.48464 (2)	0.02700 (6)	0.41131 (2)	0.02358 (12)
Cl2	0.45673 (2)	0.28133 (7)	0.28705 (2)	0.02385 (12)
N1	0.38241 (5)	0.5414 (2)	0.29193 (7)	0.0193 (3)
N2	0.34302 (5)	0.6330 (2)	0.28416 (6)	0.0199 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0203 (6)	0.0199 (7)	0.0164 (6)	−0.0021 (5)	0.0123 (5)	−0.0010 (5)
C2	0.0205 (7)	0.0230 (7)	0.0170 (6)	−0.0001 (5)	0.0127 (5)	0.0002 (5)
C3	0.0195 (6)	0.0190 (7)	0.0164 (6)	0.0016 (5)	0.0123 (5)	0.0006 (5)
C4	0.0251 (7)	0.0194 (7)	0.0208 (6)	−0.0038 (5)	0.0165 (6)	−0.0018 (6)
C5	0.0245 (7)	0.0186 (7)	0.0184 (6)	−0.0035 (5)	0.0149 (6)	−0.0044 (5)
C6	0.0193 (6)	0.0179 (7)	0.0161 (6)	0.0022 (5)	0.0124 (5)	0.0014 (5)
C7	0.0245 (7)	0.0177 (7)	0.0214 (6)	−0.0027 (5)	0.0168 (6)	−0.0021 (5)
C8	0.0246 (7)	0.0179 (7)	0.0198 (6)	−0.0018 (5)	0.0157 (6)	−0.0039 (5)
C9	0.0256 (7)	0.0175 (7)	0.0190 (6)	0.0018 (5)	0.0171 (6)	0.0012 (5)
C10	0.0499 (10)	0.0213 (8)	0.0375 (8)	0.0005 (7)	0.0373 (8)	−0.0022 (7)
C11	0.0296 (8)	0.0337 (9)	0.0284 (7)	−0.0040 (7)	0.0232 (7)	−0.0027 (7)
C12	0.0323 (8)	0.0366 (9)	0.0246 (7)	0.0103 (7)	0.0218 (7)	0.0099 (7)
C13	0.0204 (6)	0.0203 (7)	0.0154 (6)	−0.0014 (5)	0.0118 (5)	−0.0025 (5)
C14	0.0238 (7)	0.0233 (7)	0.0223 (6)	0.0001 (6)	0.0167 (6)	−0.0008 (6)
C15	0.0295 (8)	0.0250 (8)	0.0261 (7)	−0.0028 (6)	0.0196 (6)	0.0012 (6)
C16	0.0282 (8)	0.0217 (8)	0.0198 (6)	0.0029 (6)	0.0133 (6)	0.0017 (6)
C17	0.0223 (7)	0.0308 (8)	0.0216 (7)	0.0048 (6)	0.0136 (6)	−0.0002 (6)
C18	0.0218 (7)	0.0291 (8)	0.0197 (6)	−0.0007 (6)	0.0145 (6)	−0.0021 (6)
Cl1	0.0259 (2)	0.0243 (2)	0.02326 (19)	0.00553 (13)	0.01777 (16)	0.00450 (13)
Cl2	0.0253 (2)	0.0312 (2)	0.02177 (19)	0.00330 (13)	0.01869 (16)	0.00240 (13)
N1	0.0210 (6)	0.0201 (6)	0.0174 (5)	−0.0001 (5)	0.0132 (5)	−0.0006 (5)
N2	0.0212 (6)	0.0217 (6)	0.0181 (5)	−0.0003 (5)	0.0138 (5)	−0.0009 (5)

Geometric parameters (Å, º) top

C1—C2	1.344 (2)	C10—H10C	0.9800
C1—N1	1.4205 (19)	C11—H11A	0.9800
C1—C3	1.4886 (19)	C11—H11B	0.9800
C2—Cl1	1.7146 (15)	C11—H11C	0.9800
C2—Cl2	1.7240 (15)	C12—H12A	0.9800
C3—C8	1.388 (2)	C12—H12B	0.9800
C3—C4	1.396 (2)	C12—H12C	0.9800
C4—C5	1.391 (2)	C13—C18	1.394 (2)
C4—H4	0.9500	C13—C14	1.398 (2)
C5—C6	1.395 (2)	C13—N2	1.4269 (19)
C5—H5	0.9500	C14—C15	1.383 (2)
C6—C7	1.396 (2)	C14—H14	0.9500
C6—C9	1.5381 (19)	C15—C16	1.390 (2)
C7—C8	1.393 (2)	C15—H15	0.9500
C7—H7	0.9500	C16—C17	1.391 (2)
C8—H8	0.9500	C16—H16	0.9500
C9—C11	1.532 (2)	C17—C18	1.388 (2)
C9—C10	1.532 (2)	C17—H17	0.9500
C9—C12	1.536 (2)	C18—H18	0.9500
C10—H10A	0.9800	N1—N2	1.2628 (18)
C10—H10B	0.9800

C2—C1—N1	115.21 (13)	H10A—C10—H10C	109.5
C2—C1—C3	123.29 (13)	H10B—C10—H10C	109.5
N1—C1—C3	121.45 (13)	C9—C11—H11A	109.5
C1—C2—Cl1	122.94 (12)	C9—C11—H11B	109.5
C1—C2—Cl2	123.42 (12)	H11A—C11—H11B	109.5
Cl1—C2—Cl2	113.64 (9)	C9—C11—H11C	109.5
C8—C3—C4	118.41 (13)	H11A—C11—H11C	109.5
C8—C3—C1	122.15 (13)	H11B—C11—H11C	109.5
C4—C3—C1	119.42 (13)	C9—C12—H12A	109.5
C5—C4—C3	120.69 (14)	C9—C12—H12B	109.5
C5—C4—H4	119.7	H12A—C12—H12B	109.5
C3—C4—H4	119.7	C9—C12—H12C	109.5
C4—C5—C6	121.41 (13)	H12A—C12—H12C	109.5
C4—C5—H5	119.3	H12B—C12—H12C	109.5
C6—C5—H5	119.3	C18—C13—C14	120.28 (14)
C5—C6—C7	117.28 (13)	C18—C13—N2	115.83 (13)
C5—C6—C9	121.94 (13)	C14—C13—N2	123.75 (13)
C7—C6—C9	120.78 (13)	C15—C14—C13	119.32 (14)
C8—C7—C6	121.63 (14)	C15—C14—H14	120.3
C8—C7—H7	119.2	C13—C14—H14	120.3
C6—C7—H7	119.2	C14—C15—C16	120.54 (15)
C3—C8—C7	120.55 (13)	C14—C15—H15	119.7
C3—C8—H8	119.7	C16—C15—H15	119.7
C7—C8—H8	119.7	C15—C16—C17	120.12 (15)
C11—C9—C10	107.75 (13)	C15—C16—H16	119.9
C11—C9—C12	109.54 (13)	C17—C16—H16	119.9
C10—C9—C12	108.60 (13)	C18—C17—C16	119.81 (14)
C11—C9—C6	110.65 (12)	C18—C17—H17	120.1
C10—C9—C6	111.93 (12)	C16—C17—H17	120.1
C12—C9—C6	108.33 (12)	C17—C18—C13	119.91 (14)
C9—C10—H10A	109.5	C17—C18—H18	120.0
C9—C10—H10B	109.5	C13—C18—H18	120.0
H10A—C10—H10B	109.5	N2—N1—C1	113.43 (12)
C9—C10—H10C	109.5	N1—N2—C13	113.31 (12)

N1—C1—C2—Cl1	−179.36 (10)	C7—C6—C9—C11	−37.58 (18)
C3—C1—C2—Cl1	3.2 (2)	C5—C6—C9—C10	23.30 (19)
N1—C1—C2—Cl2	−0.05 (19)	C7—C6—C9—C10	−157.77 (14)
C3—C1—C2—Cl2	−177.52 (11)	C5—C6—C9—C12	−96.41 (16)
C2—C1—C3—C8	−67.0 (2)	C7—C6—C9—C12	82.52 (17)
N1—C1—C3—C8	115.67 (16)	C18—C13—C14—C15	1.1 (2)
C2—C1—C3—C4	114.42 (17)	N2—C13—C14—C15	−174.40 (14)
N1—C1—C3—C4	−62.90 (18)	C13—C14—C15—C16	−0.8 (2)
C8—C3—C4—C5	−1.2 (2)	C14—C15—C16—C17	−0.6 (2)
C1—C3—C4—C5	177.40 (13)	C15—C16—C17—C18	1.6 (2)
C3—C4—C5—C6	−0.2 (2)	C16—C17—C18—C13	−1.3 (2)
C4—C5—C6—C7	1.7 (2)	C14—C13—C18—C17	−0.1 (2)
C4—C5—C6—C9	−179.38 (13)	N2—C13—C18—C17	175.75 (13)
C5—C6—C7—C8	−1.8 (2)	C2—C1—N1—N2	169.00 (13)
C9—C6—C7—C8	179.25 (13)	C3—C1—N1—N2	−13.47 (19)
C4—C3—C8—C7	1.1 (2)	C1—N1—N2—C13	177.31 (11)
C1—C3—C8—C7	−177.48 (13)	C18—C13—N2—N1	168.30 (13)
C6—C7—C8—C3	0.4 (2)	C14—C13—N2—N1	−16.0 (2)
C5—C6—C9—C11	143.50 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the 4-tert-butylphenyl ring (C3–C8).

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···Cg1ⁱ	0.95	2.95	3.476 (2)	116

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

(E)-1-[1-(4-tert-Butylphenyl)-2,2-dichloroethenyl]-2-\ (4-methylphenyl)diazene (II) top

Crystal data top

C₁₉H₂₀Cl₂N₂	F(000) = 1456
M_r = 347.27	D_x = 1.280 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
a = 30.9062 (6) Å	Cell parameters from 19033 reflections
b = 6.27248 (5) Å	θ = 3.6–77.1°
c = 23.3475 (4) Å	µ = 3.23 mm⁻¹
β = 127.223 (3)°	T = 100 K
V = 3604.08 (15) Å³	Prism, red
Z = 8	0.19 × 0.17 × 0.14 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	3643 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube	R_int = 0.047
φ and ω scans	θ_max = 77.5°, θ_min = 3.6°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021)	h = −38→38
T_min = 0.464, T_max = 0.630	k = −6→7
28692 measured reflections	l = −29→29
3805 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.033	w = 1/[σ²(F_o²) + (0.047P)² + 2.8P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.090	(Δ/σ)_max = 0.001
S = 1.10	Δρ_max = 0.29 e Å⁻³
3805 reflections	Δρ_min = −0.30 e Å⁻³
213 parameters	Extinction correction: SHELXL2016/6 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00017 (5)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.48998 (2)	0.03552 (5)	0.41749 (2)	0.02454 (11)
Cl2	0.46363 (2)	0.25942 (5)	0.29246 (2)	0.02446 (11)
N1	0.39101 (4)	0.51844 (18)	0.30369 (6)	0.0208 (2)
N2	0.35039 (5)	0.59579 (18)	0.29674 (6)	0.0222 (2)
C1	0.41805 (5)	0.3591 (2)	0.35785 (7)	0.0201 (3)
C2	0.45276 (5)	0.2354 (2)	0.35637 (7)	0.0208 (3)
C3	0.40920 (5)	0.3421 (2)	0.41360 (7)	0.0195 (3)
C4	0.42254 (6)	0.5155 (2)	0.45907 (7)	0.0227 (3)
H4	0.438159	0.639440	0.455003	0.027*
C5	0.41316 (6)	0.5082 (2)	0.51023 (7)	0.0220 (3)
H5	0.422523	0.627803	0.540667	0.026*
C6	0.39028 (5)	0.3292 (2)	0.51781 (7)	0.0191 (3)
C7	0.37776 (5)	0.1560 (2)	0.47236 (7)	0.0211 (3)
H7	0.362819	0.030753	0.477002	0.025*
C8	0.38657 (5)	0.1621 (2)	0.42057 (7)	0.0209 (3)
H8	0.377088	0.042930	0.389929	0.025*
C9	0.38015 (5)	0.3145 (2)	0.57443 (7)	0.0206 (3)
C10	0.38607 (6)	0.5300 (2)	0.60923 (8)	0.0284 (3)
H10A	0.423263	0.582766	0.634072	0.043*
H10B	0.378300	0.513209	0.643923	0.043*
H10C	0.360454	0.632136	0.571982	0.043*
C11	0.32232 (6)	0.2333 (3)	0.53954 (8)	0.0295 (3)
H11A	0.296101	0.325794	0.499032	0.044*
H11B	0.315190	0.234963	0.575128	0.044*
H11C	0.318734	0.087345	0.522185	0.044*
C12	0.42191 (6)	0.1599 (3)	0.63358 (8)	0.0315 (3)
H12A	0.417802	0.019311	0.612496	0.047*
H12B	0.415934	0.147896	0.670170	0.047*
H12C	0.458667	0.213787	0.655851	0.047*
C13	0.32527 (5)	0.7652 (2)	0.24618 (7)	0.0199 (3)
C14	0.35328 (5)	0.8930 (2)	0.22966 (7)	0.0221 (3)
H14	0.390374	0.865296	0.250923	0.027*
C15	0.32646 (6)	1.0606 (2)	0.18195 (8)	0.0252 (3)
H15	0.345643	1.148864	0.171144	0.030*
C16	0.27186 (6)	1.1026 (2)	0.14946 (7)	0.0247 (3)
C17	0.24436 (6)	0.9736 (2)	0.16630 (8)	0.0263 (3)
H17	0.206996	0.999041	0.144008	0.032*
C18	0.27109 (6)	0.8078 (2)	0.21550 (8)	0.0261 (3)
H18	0.252413	0.723936	0.228125	0.031*
C19	0.24335 (7)	1.2860 (3)	0.09755 (9)	0.0361 (4)
H19A	0.204956	1.250175	0.061231	0.054*
H19B	0.260343	1.313112	0.073900	0.054*
H19C	0.246248	1.413799	0.123816	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02633 (18)	0.02606 (18)	0.02459 (17)	0.00732 (11)	0.01716 (14)	0.00613 (11)
Cl2	0.02460 (18)	0.03214 (19)	0.02356 (17)	0.00413 (12)	0.01819 (15)	0.00397 (11)
N1	0.0216 (5)	0.0219 (5)	0.0208 (5)	0.0017 (4)	0.0139 (4)	0.0011 (4)
N2	0.0225 (5)	0.0241 (5)	0.0229 (5)	0.0014 (4)	0.0153 (5)	0.0021 (4)
C1	0.0210 (6)	0.0207 (6)	0.0197 (6)	−0.0009 (5)	0.0129 (5)	0.0008 (5)
C2	0.0207 (6)	0.0241 (6)	0.0192 (6)	0.0006 (5)	0.0129 (5)	0.0022 (5)
C3	0.0192 (6)	0.0211 (6)	0.0194 (6)	0.0021 (5)	0.0123 (5)	0.0018 (5)
C4	0.0268 (7)	0.0202 (6)	0.0242 (6)	−0.0034 (5)	0.0170 (6)	−0.0009 (5)
C5	0.0256 (6)	0.0201 (6)	0.0229 (6)	−0.0030 (5)	0.0160 (5)	−0.0029 (5)
C6	0.0178 (6)	0.0210 (6)	0.0191 (6)	0.0023 (5)	0.0115 (5)	0.0014 (5)
C7	0.0246 (6)	0.0184 (6)	0.0253 (6)	−0.0019 (5)	0.0177 (5)	−0.0005 (5)
C8	0.0236 (6)	0.0190 (6)	0.0227 (6)	−0.0001 (5)	0.0153 (5)	−0.0016 (5)
C9	0.0223 (6)	0.0225 (6)	0.0213 (6)	−0.0007 (5)	0.0154 (5)	−0.0007 (5)
C10	0.0361 (8)	0.0275 (7)	0.0312 (7)	−0.0034 (6)	0.0255 (7)	−0.0064 (6)
C11	0.0278 (7)	0.0386 (8)	0.0303 (7)	−0.0081 (6)	0.0218 (6)	−0.0078 (6)
C12	0.0361 (8)	0.0381 (8)	0.0308 (7)	0.0110 (6)	0.0258 (7)	0.0103 (6)
C13	0.0225 (6)	0.0208 (6)	0.0188 (6)	0.0018 (5)	0.0138 (5)	0.0002 (5)
C14	0.0208 (6)	0.0237 (6)	0.0245 (6)	0.0015 (5)	0.0151 (5)	0.0008 (5)
C15	0.0266 (7)	0.0237 (6)	0.0287 (7)	0.0010 (5)	0.0185 (6)	0.0036 (5)
C16	0.0274 (7)	0.0218 (6)	0.0230 (6)	0.0036 (5)	0.0143 (6)	0.0002 (5)
C17	0.0217 (6)	0.0290 (7)	0.0284 (7)	0.0048 (5)	0.0151 (6)	0.0016 (5)
C18	0.0243 (7)	0.0299 (7)	0.0293 (7)	0.0016 (5)	0.0189 (6)	0.0026 (6)
C19	0.0327 (8)	0.0305 (8)	0.0383 (8)	0.0102 (6)	0.0180 (7)	0.0111 (6)

Geometric parameters (Å, º) top

Cl1—C2	1.7163 (13)	C10—H10B	0.9800
Cl2—C2	1.7229 (13)	C10—H10C	0.9800
N1—N2	1.2613 (16)	C11—H11A	0.9800
N1—C1	1.4202 (16)	C11—H11B	0.9800
N2—C13	1.4199 (17)	C11—H11C	0.9800
C1—C2	1.3415 (19)	C12—H12A	0.9800
C1—C3	1.4871 (17)	C12—H12B	0.9800
C3—C8	1.3887 (18)	C12—H12C	0.9800
C3—C4	1.3964 (18)	C13—C18	1.3921 (19)
C4—C5	1.3898 (19)	C13—C14	1.3944 (18)
C4—H4	0.9500	C14—C15	1.3844 (19)
C5—C6	1.3942 (18)	C14—H14	0.9500
C5—H5	0.9500	C15—C16	1.394 (2)
C6—C7	1.3995 (18)	C15—H15	0.9500
C6—C9	1.5348 (17)	C16—C17	1.391 (2)
C7—C8	1.3915 (18)	C16—C19	1.5089 (19)
C7—H7	0.9500	C17—C18	1.391 (2)
C8—H8	0.9500	C17—H17	0.9500
C9—C10	1.5303 (18)	C18—H18	0.9500
C9—C11	1.5349 (18)	C19—H19A	0.9800
C9—C12	1.5353 (19)	C19—H19B	0.9800
C10—H10A	0.9800	C19—H19C	0.9800

N2—N1—C1	112.90 (11)	H10B—C10—H10C	109.5
N1—N2—C13	113.32 (10)	C9—C11—H11A	109.5
C2—C1—N1	115.67 (11)	C9—C11—H11B	109.5
C2—C1—C3	123.67 (12)	H11A—C11—H11B	109.5
N1—C1—C3	120.60 (11)	C9—C11—H11C	109.5
C1—C2—Cl1	123.05 (10)	H11A—C11—H11C	109.5
C1—C2—Cl2	123.35 (10)	H11B—C11—H11C	109.5
Cl1—C2—Cl2	113.60 (7)	C9—C12—H12A	109.5
C8—C3—C4	118.82 (12)	C9—C12—H12B	109.5
C8—C3—C1	122.23 (12)	H12A—C12—H12B	109.5
C4—C3—C1	118.92 (11)	C9—C12—H12C	109.5
C5—C4—C3	120.59 (12)	H12A—C12—H12C	109.5
C5—C4—H4	119.7	H12B—C12—H12C	109.5
C3—C4—H4	119.7	C18—C13—C14	120.14 (12)
C4—C5—C6	121.38 (12)	C18—C13—N2	117.00 (12)
C4—C5—H5	119.3	C14—C13—N2	122.78 (12)
C6—C5—H5	119.3	C15—C14—C13	119.31 (12)
C5—C6—C7	117.26 (11)	C15—C14—H14	120.3
C5—C6—C9	122.75 (11)	C13—C14—H14	120.3
C7—C6—C9	119.96 (11)	C14—C15—C16	121.31 (13)
C8—C7—C6	121.85 (12)	C14—C15—H15	119.3
C8—C7—H7	119.1	C16—C15—H15	119.3
C6—C7—H7	119.1	C17—C16—C15	118.81 (12)
C3—C8—C7	120.09 (12)	C17—C16—C19	120.69 (13)
C3—C8—H8	120.0	C15—C16—C19	120.49 (13)
C7—C8—H8	120.0	C18—C17—C16	120.58 (13)
C10—C9—C6	112.52 (11)	C18—C17—H17	119.7
C10—C9—C11	107.56 (11)	C16—C17—H17	119.7
C6—C9—C11	109.98 (10)	C17—C18—C13	119.81 (13)
C10—C9—C12	108.35 (12)	C17—C18—H18	120.1
C6—C9—C12	108.31 (10)	C13—C18—H18	120.1
C11—C9—C12	110.09 (12)	C16—C19—H19A	109.5
C9—C10—H10A	109.5	C16—C19—H19B	109.5
C9—C10—H10B	109.5	H19A—C19—H19B	109.5
H10A—C10—H10B	109.5	C16—C19—H19C	109.5
C9—C10—H10C	109.5	H19A—C19—H19C	109.5
H10A—C10—H10C	109.5	H19B—C19—H19C	109.5

C1—N1—N2—C13	175.97 (11)	C6—C7—C8—C3	1.1 (2)
N2—N1—C1—C2	164.44 (12)	C5—C6—C9—C10	12.41 (17)
N2—N1—C1—C3	−18.16 (17)	C7—C6—C9—C10	−169.31 (12)
N1—C1—C2—Cl1	179.34 (9)	C5—C6—C9—C11	132.31 (13)
C3—C1—C2—Cl1	2.03 (19)	C7—C6—C9—C11	−49.41 (16)
N1—C1—C2—Cl2	−1.51 (18)	C5—C6—C9—C12	−107.35 (14)
C3—C1—C2—Cl2	−178.82 (10)	C7—C6—C9—C12	70.94 (15)
C2—C1—C3—C8	−65.16 (18)	N1—N2—C13—C18	157.20 (12)
N1—C1—C3—C8	117.65 (14)	N1—N2—C13—C14	−26.07 (18)
C2—C1—C3—C4	116.87 (15)	C18—C13—C14—C15	−0.7 (2)
N1—C1—C3—C4	−60.31 (17)	N2—C13—C14—C15	−177.35 (12)
C8—C3—C4—C5	−0.2 (2)	C13—C14—C15—C16	−0.8 (2)
C1—C3—C4—C5	177.83 (12)	C14—C15—C16—C17	0.7 (2)
C3—C4—C5—C6	0.0 (2)	C14—C15—C16—C19	−179.95 (14)
C4—C5—C6—C7	0.74 (19)	C15—C16—C17—C18	0.9 (2)
C4—C5—C6—C9	179.07 (12)	C19—C16—C17—C18	−178.43 (14)
C5—C6—C7—C8	−1.27 (19)	C16—C17—C18—C13	−2.4 (2)
C9—C6—C7—C8	−179.65 (12)	C14—C13—C18—C17	2.3 (2)
C4—C3—C8—C7	−0.30 (19)	N2—C13—C18—C17	179.13 (12)
C1—C3—C8—C7	−178.27 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the 4-tert-butylphenyl ring (C3–C8).

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···Cg1ⁱ	0.95	2.88	3.675 (2)	142

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

(E)-1-[1-(4-tert-Butylphenyl)-2,2-dichloroethenyl]-2-(4-methoxyphenyl)diazene (III) top

Crystal data top

C₁₉H₂₀Cl₂N₂O	F(000) = 760
M_r = 363.27	D_x = 1.323 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 13.8738 (2) Å	Cell parameters from 17727 reflections
b = 12.5946 (2) Å	θ = 3.4–77.6°
c = 11.3013 (1) Å	µ = 3.26 mm⁻¹
β = 112.505 (1)°	T = 100 K
V = 1824.35 (4) Å³	Prism, red
Z = 4	0.24 × 0.20 × 0.18 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	3603 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube	R_int = 0.076
φ and ω scans	θ_max = 77.9°, θ_min = 3.5°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021)	h = −15→17
T_min = 0.431, T_max = 0.550	k = −15→15
25894 measured reflections	l = −14→14
3843 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.118	w = 1/[σ²(F_o²) + (0.0831P)² + 0.4008P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3843 reflections	Δρ_max = 0.53 e Å⁻³
221 parameters	Δρ_min = −0.33 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.20324 (11)	0.34882 (11)	0.22693 (13)	0.0187 (3)
C2	0.14902 (11)	0.30352 (11)	0.11245 (13)	0.0202 (3)
C3	0.19934 (10)	0.46520 (11)	0.24859 (12)	0.0176 (3)
C4	0.13412 (10)	0.50501 (11)	0.30620 (13)	0.0189 (3)
H4	0.093607	0.457391	0.333412	0.023*
C5	0.12770 (10)	0.61349 (11)	0.32425 (13)	0.0188 (3)
H5	0.081387	0.638876	0.361713	0.023*
C6	0.18772 (10)	0.68598 (11)	0.28860 (12)	0.0170 (3)
C7	0.25514 (11)	0.64453 (12)	0.23454 (14)	0.0213 (3)
H7	0.298483	0.691647	0.211415	0.026*
C8	0.26040 (11)	0.53661 (12)	0.21381 (13)	0.0214 (3)
H8	0.306116	0.511166	0.175511	0.026*
C9	0.18118 (11)	0.80655 (11)	0.30498 (13)	0.0205 (3)
C10	0.09974 (13)	0.83569 (12)	0.35970 (16)	0.0268 (3)
H10A	0.030833	0.811599	0.301035	0.040*
H10B	0.098759	0.912885	0.370051	0.040*
H10C	0.117338	0.801296	0.443148	0.040*
C11	0.28773 (13)	0.84892 (13)	0.39614 (16)	0.0282 (3)
H11A	0.305696	0.817148	0.481074	0.042*
H11B	0.284263	0.926299	0.402705	0.042*
H11C	0.341121	0.830301	0.362727	0.042*
C12	0.15139 (14)	0.86056 (13)	0.17359 (15)	0.0298 (3)
H12A	0.205161	0.845923	0.139406	0.045*
H12B	0.145827	0.937393	0.183169	0.045*
H12C	0.084214	0.832769	0.114538	0.045*
C13	0.37438 (10)	0.24915 (11)	0.52562 (13)	0.0184 (3)
C14	0.39042 (11)	0.14261 (11)	0.50182 (13)	0.0193 (3)
H14	0.360543	0.115106	0.417218	0.023*
C15	0.44961 (11)	0.07799 (11)	0.60150 (13)	0.0198 (3)
H15	0.461097	0.006053	0.585247	0.024*
C16	0.49311 (10)	0.11785 (11)	0.72709 (13)	0.0186 (3)
C17	0.47838 (11)	0.22386 (11)	0.75109 (13)	0.0199 (3)
H17	0.508107	0.251380	0.835695	0.024*
C18	0.41964 (11)	0.28891 (11)	0.64970 (13)	0.0206 (3)
H18	0.410262	0.361533	0.665345	0.025*
C19	0.59249 (13)	0.08155 (13)	0.94780 (14)	0.0275 (3)
H19A	0.641917	0.139312	0.955751	0.041*
H19B	0.629032	0.022336	1.003028	0.041*
H19C	0.536817	0.107057	0.973833	0.041*
Cl1	0.07489 (3)	0.37510 (3)	−0.01999 (3)	0.02558 (13)
Cl2	0.14590 (3)	0.16875 (3)	0.08679 (3)	0.02464 (13)
N1	0.26151 (9)	0.27761 (9)	0.32441 (11)	0.0193 (2)
N2	0.31434 (9)	0.32201 (9)	0.42989 (11)	0.0195 (2)
O1	0.54829 (8)	0.04642 (8)	0.81760 (10)	0.0246 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0212 (6)	0.0180 (6)	0.0175 (6)	0.0014 (5)	0.0081 (5)	0.0008 (5)
C2	0.0227 (7)	0.0178 (6)	0.0191 (6)	−0.0003 (5)	0.0070 (5)	0.0001 (5)
C3	0.0202 (6)	0.0168 (6)	0.0139 (6)	0.0012 (5)	0.0042 (5)	0.0002 (5)
C4	0.0200 (6)	0.0193 (7)	0.0168 (6)	−0.0019 (5)	0.0064 (5)	0.0009 (5)
C5	0.0192 (6)	0.0207 (7)	0.0168 (6)	0.0004 (5)	0.0072 (5)	−0.0002 (5)
C6	0.0188 (6)	0.0167 (6)	0.0129 (6)	0.0002 (5)	0.0034 (5)	0.0002 (5)
C7	0.0237 (7)	0.0200 (7)	0.0227 (7)	−0.0028 (5)	0.0116 (6)	0.0008 (5)
C8	0.0240 (7)	0.0217 (7)	0.0219 (6)	0.0017 (5)	0.0126 (5)	0.0008 (5)
C9	0.0253 (7)	0.0156 (6)	0.0193 (6)	−0.0009 (5)	0.0071 (5)	−0.0007 (5)
C10	0.0318 (8)	0.0185 (7)	0.0316 (8)	0.0042 (6)	0.0137 (6)	−0.0015 (6)
C11	0.0293 (8)	0.0225 (7)	0.0301 (8)	−0.0055 (6)	0.0084 (6)	−0.0064 (6)
C12	0.0457 (9)	0.0192 (7)	0.0230 (7)	0.0005 (6)	0.0114 (7)	0.0031 (6)
C13	0.0204 (6)	0.0172 (6)	0.0171 (6)	−0.0002 (5)	0.0065 (5)	0.0010 (5)
C14	0.0219 (7)	0.0182 (6)	0.0179 (6)	−0.0018 (5)	0.0079 (5)	−0.0020 (5)
C15	0.0227 (6)	0.0157 (6)	0.0202 (6)	−0.0001 (5)	0.0073 (5)	−0.0005 (5)
C16	0.0181 (6)	0.0180 (7)	0.0185 (6)	0.0003 (5)	0.0056 (5)	0.0030 (5)
C17	0.0218 (6)	0.0193 (7)	0.0169 (6)	−0.0010 (5)	0.0054 (5)	−0.0012 (5)
C18	0.0242 (7)	0.0165 (6)	0.0198 (6)	−0.0001 (5)	0.0069 (5)	−0.0009 (5)
C19	0.0326 (8)	0.0238 (7)	0.0183 (7)	0.0041 (6)	0.0009 (6)	0.0018 (5)
Cl1	0.0307 (2)	0.0239 (2)	0.01655 (19)	0.00034 (12)	0.00291 (15)	0.00222 (11)
Cl2	0.0306 (2)	0.0173 (2)	0.0225 (2)	−0.00119 (12)	0.00626 (15)	−0.00440 (11)
N1	0.0219 (6)	0.0179 (6)	0.0168 (5)	0.0010 (4)	0.0059 (4)	0.0004 (4)
N2	0.0225 (6)	0.0178 (6)	0.0170 (5)	0.0010 (4)	0.0064 (5)	0.0004 (4)
O1	0.0301 (5)	0.0187 (5)	0.0190 (5)	0.0039 (4)	0.0027 (4)	0.0019 (4)

Geometric parameters (Å, º) top

C1—C2	1.349 (2)	C11—H11B	0.9800
C1—N1	1.4106 (18)	C11—H11C	0.9800
C1—C3	1.4904 (19)	C12—H12A	0.9800
C2—Cl1	1.7125 (14)	C12—H12B	0.9800
C2—Cl2	1.7196 (15)	C12—H12C	0.9800
C3—C8	1.3913 (19)	C13—C18	1.3920 (19)
C3—C4	1.3947 (19)	C13—C14	1.4029 (19)
C4—C5	1.389 (2)	C13—N2	1.4200 (18)
C4—H4	0.9500	C14—C15	1.377 (2)
C5—C6	1.3951 (19)	C14—H14	0.9500
C5—H5	0.9500	C15—C16	1.405 (2)
C6—C7	1.3993 (19)	C15—H15	0.9500
C6—C9	1.5366 (19)	C16—O1	1.3573 (17)
C7—C8	1.386 (2)	C16—C17	1.393 (2)
C7—H7	0.9500	C17—C18	1.3905 (19)
C8—H8	0.9500	C17—H17	0.9500
C9—C10	1.526 (2)	C18—H18	0.9500
C9—C11	1.538 (2)	C19—O1	1.4305 (18)
C9—C12	1.539 (2)	C19—H19A	0.9800
C10—H10A	0.9800	C19—H19B	0.9800
C10—H10B	0.9800	C19—H19C	0.9800
C10—H10C	0.9800	N1—N2	1.2658 (17)
C11—H11A	0.9800

C2—C1—N1	114.99 (12)	H11A—C11—H11B	109.5
C2—C1—C3	122.10 (13)	C9—C11—H11C	109.5
N1—C1—C3	122.89 (12)	H11A—C11—H11C	109.5
C1—C2—Cl1	122.91 (11)	H11B—C11—H11C	109.5
C1—C2—Cl2	123.23 (11)	C9—C12—H12A	109.5
Cl1—C2—Cl2	113.85 (8)	C9—C12—H12B	109.5
C8—C3—C4	118.26 (13)	H12A—C12—H12B	109.5
C8—C3—C1	121.67 (12)	C9—C12—H12C	109.5
C4—C3—C1	120.07 (12)	H12A—C12—H12C	109.5
C5—C4—C3	120.77 (12)	H12B—C12—H12C	109.5
C5—C4—H4	119.6	C18—C13—C14	119.59 (13)
C3—C4—H4	119.6	C18—C13—N2	116.23 (12)
C4—C5—C6	121.48 (12)	C14—C13—N2	124.19 (12)
C4—C5—H5	119.3	C15—C14—C13	119.80 (13)
C6—C5—H5	119.3	C15—C14—H14	120.1
C5—C6—C7	117.03 (13)	C13—C14—H14	120.1
C5—C6—C9	122.86 (12)	C14—C15—C16	120.40 (13)
C7—C6—C9	120.10 (12)	C14—C15—H15	119.8
C8—C7—C6	121.80 (13)	C16—C15—H15	119.8
C8—C7—H7	119.1	O1—C16—C17	124.82 (13)
C6—C7—H7	119.1	O1—C16—C15	115.13 (12)
C7—C8—C3	120.60 (13)	C17—C16—C15	120.05 (12)
C7—C8—H8	119.7	C18—C17—C16	119.19 (12)
C3—C8—H8	119.7	C18—C17—H17	120.4
C10—C9—C6	111.93 (12)	C16—C17—H17	120.4
C10—C9—C11	108.42 (12)	C17—C18—C13	120.95 (13)
C6—C9—C11	109.73 (12)	C17—C18—H18	119.5
C10—C9—C12	108.52 (13)	C13—C18—H18	119.5
C6—C9—C12	109.09 (11)	O1—C19—H19A	109.5
C11—C9—C12	109.10 (13)	O1—C19—H19B	109.5
C9—C10—H10A	109.5	H19A—C19—H19B	109.5
C9—C10—H10B	109.5	O1—C19—H19C	109.5
H10A—C10—H10B	109.5	H19A—C19—H19C	109.5
C9—C10—H10C	109.5	H19B—C19—H19C	109.5
H10A—C10—H10C	109.5	N2—N1—C1	114.00 (12)
H10B—C10—H10C	109.5	N1—N2—C13	113.04 (11)
C9—C11—H11A	109.5	C16—O1—C19	117.79 (11)
C9—C11—H11B	109.5

N1—C1—C2—Cl1	−178.80 (10)	C7—C6—C9—C11	−62.26 (17)
C3—C1—C2—Cl1	2.57 (19)	C5—C6—C9—C12	−122.02 (15)
N1—C1—C2—Cl2	2.48 (18)	C7—C6—C9—C12	57.21 (17)
C3—C1—C2—Cl2	−176.14 (10)	C18—C13—C14—C15	0.8 (2)
C2—C1—C3—C8	−82.01 (18)	N2—C13—C14—C15	−179.66 (12)
N1—C1—C3—C8	99.47 (16)	C13—C14—C15—C16	0.7 (2)
C2—C1—C3—C4	98.64 (16)	C14—C15—C16—O1	178.87 (12)
N1—C1—C3—C4	−79.88 (17)	C14—C15—C16—C17	−1.4 (2)
C8—C3—C4—C5	2.2 (2)	O1—C16—C17—C18	−179.72 (13)
C1—C3—C4—C5	−178.43 (12)	C15—C16—C17—C18	0.5 (2)
C3—C4—C5—C6	−1.6 (2)	C16—C17—C18—C13	1.0 (2)
C4—C5—C6—C7	−0.37 (19)	C14—C13—C18—C17	−1.7 (2)
C4—C5—C6—C9	178.89 (12)	N2—C13—C18—C17	178.79 (12)
C5—C6—C7—C8	1.7 (2)	C2—C1—N1—N2	177.92 (12)
C9—C6—C7—C8	−177.56 (13)	C3—C1—N1—N2	−3.46 (18)
C6—C7—C8—C3	−1.1 (2)	C1—N1—N2—C13	−178.51 (11)
C4—C3—C8—C7	−0.9 (2)	C18—C13—N2—N1	−168.92 (12)
C1—C3—C8—C7	179.78 (13)	C14—C13—N2—N1	11.54 (18)
C5—C6—C9—C10	−1.92 (18)	C17—C16—O1—C19	1.7 (2)
C7—C6—C9—C10	177.32 (13)	C15—C16—O1—C19	−178.58 (13)
C5—C6—C9—C11	118.51 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the 4-tert-butylphenyl ring (C3–C8).

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O1ⁱ	0.95	2.39	3.2753 (17)	155
C19—H19B···Cg1ⁱⁱ	0.98	2.87	3.4276 (17)	117

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

(E)-1-[1-(4-tert-Butylphenyl)-2,2-dichloroethenyl]-2-\ (3-methylphenyl)δiazene (IV) top

Crystal data top

C₁₉H₂₀Cl₂N₂	Z = 4
M_r = 347.27	F(000) = 728
Triclinic, P1	D_x = 1.295 Mg m⁻³
a = 9.8352 (2) Å	Cu Kα radiation, λ = 1.54184 Å
b = 11.8401 (2) Å	Cell parameters from 36250 reflections
c = 16.3964 (2) Å	θ = 2.7–77.7°
α = 98.397 (1)°	µ = 3.27 mm⁻¹
β = 96.189 (1)°	T = 100 K
γ = 107.149 (1)°	Prism, red
V = 1781.77 (5) Å³	0.25 × 0.22 × 0.18 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	6948 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube	R_int = 0.071
φ and ω scans	θ_max = 77.9°, θ_min = 2.8°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021)	h = −12→12
T_min = 0.328, T_max = 0.550	k = −14→12
53607 measured reflections	l = −20→20
7515 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.058	H-atom parameters constrained
wR(F²) = 0.171	w = 1/[σ²(F_o²) + (0.1247P)² + 0.6991P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
7515 reflections	Δρ_max = 0.93 e Å⁻³
423 parameters	Δρ_min = −0.63 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.61178 (18)	0.35073 (16)	0.16342 (12)	0.0249 (4)
C2	0.6208 (2)	0.27286 (17)	0.09726 (12)	0.0286 (4)
C3	0.58777 (18)	0.31800 (15)	0.24597 (11)	0.0230 (3)
C4	0.46666 (19)	0.32673 (16)	0.28085 (12)	0.0265 (4)
H4	0.393723	0.347551	0.249429	0.032*
C5	0.45226 (19)	0.30530 (16)	0.36066 (12)	0.0265 (4)
H5	0.369067	0.311600	0.383040	0.032*
C6	0.55770 (18)	0.27437 (15)	0.40967 (11)	0.0239 (3)
C7	0.67636 (19)	0.26365 (16)	0.37312 (12)	0.0255 (4)
H7	0.748785	0.241541	0.403958	0.031*
C8	0.69106 (18)	0.28451 (16)	0.29288 (12)	0.0255 (4)
H8	0.772654	0.275817	0.269671	0.031*
C9	0.5398 (2)	0.25476 (16)	0.49849 (12)	0.0272 (4)
C10	0.5205 (2)	0.36724 (18)	0.54994 (13)	0.0333 (4)
H10A	0.603703	0.437581	0.550108	0.050*
H10B	0.512989	0.355418	0.607413	0.050*
H10C	0.432478	0.380217	0.525009	0.050*
C11	0.4060 (2)	0.14560 (18)	0.49507 (13)	0.0344 (4)
H11A	0.320435	0.160683	0.468623	0.052*
H11B	0.394079	0.132610	0.551906	0.052*
H11C	0.418147	0.073943	0.462518	0.052*
C12	0.6708 (2)	0.2312 (2)	0.54356 (13)	0.0343 (4)
H12A	0.681949	0.157211	0.513836	0.051*
H12B	0.656545	0.222374	0.600823	0.051*
H12C	0.757630	0.298939	0.544841	0.051*
C13	0.67080 (18)	0.66543 (17)	0.20121 (12)	0.0267 (4)
C14	0.67993 (19)	0.69894 (17)	0.12348 (12)	0.0273 (4)
H14	0.659272	0.638881	0.074597	0.033*
C15	0.7192 (2)	0.81996 (18)	0.11699 (13)	0.0300 (4)
C16	0.7485 (2)	0.90601 (17)	0.18984 (13)	0.0313 (4)
H16	0.776188	0.988838	0.186220	0.038*
C17	0.7382 (2)	0.87368 (18)	0.26740 (13)	0.0313 (4)
H17	0.757830	0.933887	0.316095	0.038*
C18	0.69929 (19)	0.75318 (17)	0.27368 (13)	0.0284 (4)
H18	0.691972	0.730266	0.326601	0.034*
C19	0.7313 (3)	0.85617 (19)	0.03339 (14)	0.0372 (5)
H19A	0.681665	0.915895	0.027531	0.056*
H19B	0.686864	0.785258	−0.010902	0.056*
H19C	0.833165	0.891001	0.028971	0.056*
C20	0.91894 (19)	0.62019 (16)	0.82034 (12)	0.0257 (4)
C21	0.9535 (2)	0.69058 (16)	0.89645 (12)	0.0290 (4)
C22	0.87259 (19)	0.48653 (16)	0.80936 (11)	0.0237 (3)
C23	0.72883 (19)	0.41702 (17)	0.79251 (12)	0.0278 (4)
H23	0.656334	0.454890	0.787674	0.033*
C24	0.68937 (18)	0.29242 (16)	0.78259 (12)	0.0261 (4)
H24	0.589993	0.246660	0.771607	0.031*
C25	0.79213 (18)	0.23299 (15)	0.78837 (11)	0.0228 (3)
C26	0.93658 (19)	0.30439 (17)	0.80626 (12)	0.0286 (4)
H26	1.009196	0.266638	0.811020	0.034*
C27	0.97708 (19)	0.42862 (17)	0.81727 (13)	0.0292 (4)
H27	1.076283	0.474732	0.830261	0.035*
C28	0.75234 (19)	0.09595 (16)	0.77649 (11)	0.0253 (4)
C29	0.5908 (2)	0.03328 (16)	0.74827 (13)	0.0306 (4)
H29A	0.537672	0.059455	0.790546	0.046*
H29B	0.570431	−0.054050	0.741081	0.046*
H29C	0.560719	0.054255	0.695097	0.046*
C30	0.8320 (2)	0.05048 (18)	0.70974 (14)	0.0341 (4)
H30A	0.808999	0.077558	0.657793	0.051*
H30B	0.801615	−0.037641	0.699604	0.051*
H30C	0.936143	0.082550	0.729276	0.051*
C31	0.7981 (2)	0.06146 (18)	0.85985 (14)	0.0369 (5)
H31A	0.902082	0.099535	0.877774	0.055*
H31B	0.774929	−0.026150	0.852401	0.055*
H31C	0.746315	0.089054	0.902386	0.055*
C32	0.92807 (19)	0.68230 (17)	0.61640 (12)	0.0254 (4)
C33	0.90203 (19)	0.61415 (17)	0.53664 (12)	0.0279 (4)
H33	0.868253	0.528857	0.529137	0.034*
C34	0.9247 (2)	0.66907 (18)	0.46696 (12)	0.0293 (4)
C35	0.9724 (2)	0.79377 (18)	0.48010 (13)	0.0310 (4)
H35	0.988008	0.832852	0.433702	0.037*
C36	0.9977 (2)	0.86290 (18)	0.55985 (13)	0.0328 (4)
H36	1.029797	0.948185	0.567020	0.039*
C37	0.9767 (2)	0.80869 (17)	0.62886 (12)	0.0293 (4)
H37	0.994786	0.855806	0.683334	0.035*
C38	0.8987 (3)	0.5940 (2)	0.38145 (13)	0.0393 (5)
H38A	0.955999	0.538846	0.381276	0.059*
H38B	0.926960	0.646511	0.341058	0.059*
H38C	0.796204	0.547539	0.366089	0.059*
Cl1	0.58942 (6)	0.12256 (4)	0.09905 (3)	0.03558 (15)
Cl2	0.66274 (6)	0.31202 (5)	0.00425 (3)	0.03661 (15)
Cl3	0.93882 (6)	0.63467 (4)	0.98652 (3)	0.03543 (15)
Cl4	1.01859 (6)	0.84553 (4)	0.91208 (3)	0.03931 (16)
N1	0.63865 (16)	0.47049 (14)	0.15050 (10)	0.0266 (3)
N2	0.63619 (16)	0.54441 (14)	0.21407 (10)	0.0260 (3)
N3	0.93773 (17)	0.68198 (14)	0.75331 (10)	0.0269 (3)
N4	0.90357 (16)	0.61543 (14)	0.68230 (10)	0.0264 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0242 (8)	0.0224 (8)	0.0308 (9)	0.0099 (6)	0.0048 (6)	0.0082 (7)
C2	0.0314 (9)	0.0264 (9)	0.0314 (9)	0.0123 (7)	0.0071 (7)	0.0083 (7)
C3	0.0257 (8)	0.0165 (7)	0.0286 (9)	0.0091 (6)	0.0043 (6)	0.0050 (6)
C4	0.0261 (8)	0.0235 (9)	0.0346 (9)	0.0135 (7)	0.0045 (7)	0.0085 (7)
C5	0.0254 (8)	0.0246 (9)	0.0339 (10)	0.0126 (7)	0.0073 (7)	0.0075 (7)
C6	0.0260 (8)	0.0180 (8)	0.0289 (9)	0.0088 (6)	0.0043 (7)	0.0047 (6)
C7	0.0256 (8)	0.0229 (8)	0.0308 (9)	0.0113 (6)	0.0035 (7)	0.0075 (7)
C8	0.0232 (8)	0.0231 (8)	0.0339 (9)	0.0116 (6)	0.0058 (7)	0.0067 (7)
C9	0.0302 (9)	0.0251 (9)	0.0286 (9)	0.0109 (7)	0.0061 (7)	0.0065 (7)
C10	0.0399 (10)	0.0312 (10)	0.0331 (10)	0.0164 (8)	0.0101 (8)	0.0048 (8)
C11	0.0365 (10)	0.0300 (10)	0.0355 (10)	0.0056 (8)	0.0084 (8)	0.0102 (8)
C12	0.0386 (10)	0.0387 (11)	0.0311 (10)	0.0184 (8)	0.0056 (8)	0.0107 (8)
C13	0.0223 (8)	0.0256 (9)	0.0354 (10)	0.0103 (7)	0.0055 (7)	0.0093 (7)
C14	0.0268 (8)	0.0248 (9)	0.0329 (9)	0.0121 (7)	0.0042 (7)	0.0057 (7)
C15	0.0276 (8)	0.0309 (10)	0.0346 (10)	0.0117 (7)	0.0048 (7)	0.0109 (8)
C16	0.0284 (9)	0.0236 (9)	0.0430 (11)	0.0100 (7)	0.0040 (8)	0.0075 (8)
C17	0.0306 (9)	0.0262 (9)	0.0367 (10)	0.0113 (7)	0.0027 (7)	0.0013 (7)
C18	0.0267 (8)	0.0266 (9)	0.0344 (10)	0.0118 (7)	0.0044 (7)	0.0064 (7)
C19	0.0501 (12)	0.0270 (10)	0.0386 (11)	0.0146 (9)	0.0089 (9)	0.0129 (8)
C20	0.0255 (8)	0.0235 (9)	0.0303 (9)	0.0093 (7)	0.0070 (7)	0.0070 (7)
C21	0.0361 (9)	0.0206 (8)	0.0327 (10)	0.0097 (7)	0.0094 (7)	0.0082 (7)
C22	0.0280 (8)	0.0214 (8)	0.0237 (8)	0.0101 (7)	0.0059 (6)	0.0048 (6)
C23	0.0270 (8)	0.0233 (9)	0.0364 (10)	0.0137 (7)	0.0045 (7)	0.0048 (7)
C24	0.0214 (8)	0.0232 (9)	0.0344 (9)	0.0086 (6)	0.0033 (7)	0.0053 (7)
C25	0.0269 (8)	0.0221 (8)	0.0224 (8)	0.0117 (7)	0.0042 (6)	0.0048 (6)
C26	0.0254 (8)	0.0271 (9)	0.0371 (10)	0.0145 (7)	0.0039 (7)	0.0056 (7)
C27	0.0217 (8)	0.0260 (9)	0.0398 (10)	0.0076 (7)	0.0048 (7)	0.0059 (7)
C28	0.0287 (8)	0.0212 (8)	0.0287 (9)	0.0120 (7)	0.0035 (7)	0.0052 (6)
C29	0.0303 (9)	0.0197 (8)	0.0417 (11)	0.0071 (7)	0.0063 (8)	0.0059 (7)
C30	0.0329 (9)	0.0263 (9)	0.0426 (11)	0.0127 (7)	0.0069 (8)	−0.0026 (8)
C31	0.0492 (12)	0.0264 (10)	0.0375 (11)	0.0158 (8)	−0.0009 (9)	0.0112 (8)
C32	0.0246 (8)	0.0269 (9)	0.0293 (9)	0.0130 (7)	0.0054 (7)	0.0086 (7)
C33	0.0278 (8)	0.0237 (9)	0.0336 (10)	0.0113 (7)	0.0020 (7)	0.0050 (7)
C34	0.0298 (9)	0.0309 (10)	0.0300 (9)	0.0159 (7)	0.0008 (7)	0.0041 (7)
C35	0.0352 (9)	0.0308 (10)	0.0324 (10)	0.0168 (8)	0.0052 (7)	0.0100 (7)
C36	0.0411 (10)	0.0254 (9)	0.0351 (10)	0.0147 (8)	0.0052 (8)	0.0078 (8)
C37	0.0340 (9)	0.0263 (9)	0.0315 (9)	0.0154 (7)	0.0052 (7)	0.0053 (7)
C38	0.0563 (13)	0.0344 (11)	0.0305 (10)	0.0231 (10)	−0.0010 (9)	0.0040 (8)
Cl1	0.0505 (3)	0.0238 (3)	0.0367 (3)	0.0175 (2)	0.0099 (2)	0.00496 (19)
Cl2	0.0483 (3)	0.0372 (3)	0.0302 (3)	0.0181 (2)	0.0131 (2)	0.01026 (19)
Cl3	0.0526 (3)	0.0272 (3)	0.0286 (3)	0.0135 (2)	0.0108 (2)	0.00704 (18)
Cl4	0.0583 (3)	0.0196 (2)	0.0377 (3)	0.0078 (2)	0.0127 (2)	0.00383 (18)
N1	0.0252 (7)	0.0249 (8)	0.0330 (8)	0.0104 (6)	0.0055 (6)	0.0099 (6)
N2	0.0246 (7)	0.0228 (7)	0.0335 (8)	0.0108 (6)	0.0052 (6)	0.0072 (6)
N3	0.0290 (7)	0.0252 (8)	0.0299 (8)	0.0114 (6)	0.0074 (6)	0.0079 (6)
N4	0.0253 (7)	0.0259 (8)	0.0311 (8)	0.0116 (6)	0.0044 (6)	0.0079 (6)

Geometric parameters (Å, º) top

C1—C2	1.346 (3)	C20—N3	1.406 (2)
C1—N1	1.416 (2)	C20—C22	1.489 (2)
C1—C3	1.485 (2)	C21—Cl3	1.7074 (19)
C2—Cl2	1.715 (2)	C21—Cl4	1.7252 (19)
C2—Cl1	1.7193 (19)	C22—C23	1.384 (3)
C3—C8	1.392 (2)	C22—C27	1.399 (2)
C3—C4	1.400 (2)	C23—C24	1.390 (3)
C4—C5	1.383 (3)	C23—H23	0.9500
C4—H4	0.9500	C24—C25	1.394 (2)
C5—C6	1.409 (2)	C24—H24	0.9500
C5—H5	0.9500	C25—C26	1.396 (3)
C6—C7	1.398 (2)	C25—C28	1.530 (2)
C6—C9	1.528 (2)	C26—C27	1.384 (3)
C7—C8	1.389 (3)	C26—H26	0.9500
C7—H7	0.9500	C27—H27	0.9500
C8—H8	0.9500	C28—C29	1.528 (2)
C9—C12	1.533 (3)	C28—C30	1.537 (3)
C9—C11	1.538 (3)	C28—C31	1.541 (3)
C9—C10	1.542 (3)	C29—H29A	0.9800
C10—H10A	0.9800	C29—H29B	0.9800
C10—H10B	0.9800	C29—H29C	0.9800
C10—H10C	0.9800	C30—H30A	0.9800
C11—H11A	0.9800	C30—H30B	0.9800
C11—H11B	0.9800	C30—H30C	0.9800
C11—H11C	0.9800	C31—H31A	0.9800
C12—H12A	0.9800	C31—H31B	0.9800
C12—H12B	0.9800	C31—H31C	0.9800
C12—H12C	0.9800	C32—C33	1.387 (3)
C13—C14	1.393 (3)	C32—C37	1.406 (3)
C13—C18	1.402 (3)	C32—N4	1.430 (2)
C13—N2	1.425 (2)	C33—C34	1.402 (3)
C14—C15	1.393 (3)	C33—H33	0.9500
C14—H14	0.9500	C34—C35	1.387 (3)
C15—C16	1.395 (3)	C34—C38	1.499 (3)
C15—C19	1.501 (3)	C35—C36	1.392 (3)
C16—C17	1.386 (3)	C35—H35	0.9500
C16—H16	0.9500	C36—C37	1.385 (3)
C17—C18	1.386 (3)	C36—H36	0.9500
C17—H17	0.9500	C37—H37	0.9500
C18—H18	0.9500	C38—H38A	0.9800
C19—H19A	0.9800	C38—H38B	0.9800
C19—H19B	0.9800	C38—H38C	0.9800
C19—H19C	0.9800	N1—N2	1.267 (2)
C20—C21	1.344 (3)	N3—N4	1.257 (2)

C2—C1—N1	114.51 (16)	N3—C20—C22	123.14 (16)
C2—C1—C3	123.57 (16)	C20—C21—Cl3	123.03 (15)
N1—C1—C3	121.73 (16)	C20—C21—Cl4	123.05 (15)
C1—C2—Cl2	124.11 (15)	Cl3—C21—Cl4	113.91 (11)
C1—C2—Cl1	122.10 (15)	C23—C22—C27	118.47 (16)
Cl2—C2—Cl1	113.79 (11)	C23—C22—C20	122.24 (16)
C8—C3—C4	118.29 (17)	C27—C22—C20	119.28 (16)
C8—C3—C1	120.08 (15)	C22—C23—C24	120.73 (16)
C4—C3—C1	121.52 (15)	C22—C23—H23	119.6
C5—C4—C3	120.57 (16)	C24—C23—H23	119.6
C5—C4—H4	119.7	C23—C24—C25	121.58 (16)
C3—C4—H4	119.7	C23—C24—H24	119.2
C4—C5—C6	121.76 (16)	C25—C24—H24	119.2
C4—C5—H5	119.1	C24—C25—C26	117.00 (16)
C6—C5—H5	119.1	C24—C25—C28	122.87 (15)
C7—C6—C5	116.83 (16)	C26—C25—C28	120.13 (15)
C7—C6—C9	123.00 (15)	C27—C26—C25	121.91 (16)
C5—C6—C9	120.17 (16)	C27—C26—H26	119.0
C8—C7—C6	121.65 (16)	C25—C26—H26	119.0
C8—C7—H7	119.2	C26—C27—C22	120.28 (16)
C6—C7—H7	119.2	C26—C27—H27	119.9
C7—C8—C3	120.87 (16)	C22—C27—H27	119.9
C7—C8—H8	119.6	C29—C28—C25	112.29 (14)
C3—C8—H8	119.6	C29—C28—C30	107.92 (15)
C6—C9—C12	112.17 (15)	C25—C28—C30	109.58 (15)
C6—C9—C11	109.16 (15)	C29—C28—C31	108.82 (16)
C12—C9—C11	108.39 (16)	C25—C28—C31	109.01 (15)
C6—C9—C10	109.85 (15)	C30—C28—C31	109.17 (16)
C12—C9—C10	107.88 (16)	C28—C29—H29A	109.5
C11—C9—C10	109.34 (16)	C28—C29—H29B	109.5
C9—C10—H10A	109.5	H29A—C29—H29B	109.5
C9—C10—H10B	109.5	C28—C29—H29C	109.5
H10A—C10—H10B	109.5	H29A—C29—H29C	109.5
C9—C10—H10C	109.5	H29B—C29—H29C	109.5
H10A—C10—H10C	109.5	C28—C30—H30A	109.5
H10B—C10—H10C	109.5	C28—C30—H30B	109.5
C9—C11—H11A	109.5	H30A—C30—H30B	109.5
C9—C11—H11B	109.5	C28—C30—H30C	109.5
H11A—C11—H11B	109.5	H30A—C30—H30C	109.5
C9—C11—H11C	109.5	H30B—C30—H30C	109.5
H11A—C11—H11C	109.5	C28—C31—H31A	109.5
H11B—C11—H11C	109.5	C28—C31—H31B	109.5
C9—C12—H12A	109.5	H31A—C31—H31B	109.5
C9—C12—H12B	109.5	C28—C31—H31C	109.5
H12A—C12—H12B	109.5	H31A—C31—H31C	109.5
C9—C12—H12C	109.5	H31B—C31—H31C	109.5
H12A—C12—H12C	109.5	C33—C32—C37	120.41 (17)
H12B—C12—H12C	109.5	C33—C32—N4	115.61 (16)
C14—C13—C18	120.31 (17)	C37—C32—N4	123.98 (17)
C14—C13—N2	124.27 (17)	C32—C33—C34	121.09 (17)
C18—C13—N2	115.41 (17)	C32—C33—H33	119.5
C15—C14—C13	120.41 (18)	C34—C33—H33	119.5
C15—C14—H14	119.8	C35—C34—C33	117.91 (18)
C13—C14—H14	119.8	C35—C34—C38	121.73 (18)
C14—C15—C16	118.46 (18)	C33—C34—C38	120.36 (18)
C14—C15—C19	120.42 (18)	C34—C35—C36	121.39 (18)
C16—C15—C19	121.12 (18)	C34—C35—H35	119.3
C17—C16—C15	121.63 (18)	C36—C35—H35	119.3
C17—C16—H16	119.2	C37—C36—C35	120.73 (18)
C15—C16—H16	119.2	C37—C36—H36	119.6
C16—C17—C18	119.78 (18)	C35—C36—H36	119.6
C16—C17—H17	120.1	C36—C37—C32	118.46 (18)
C18—C17—H17	120.1	C36—C37—H37	120.8
C17—C18—C13	119.40 (18)	C32—C37—H37	120.8
C17—C18—H18	120.3	C34—C38—H38A	109.5
C13—C18—H18	120.3	C34—C38—H38B	109.5
C15—C19—H19A	109.5	H38A—C38—H38B	109.5
C15—C19—H19B	109.5	C34—C38—H38C	109.5
H19A—C19—H19B	109.5	H38A—C38—H38C	109.5
C15—C19—H19C	109.5	H38B—C38—H38C	109.5
H19A—C19—H19C	109.5	N2—N1—C1	114.26 (15)
H19B—C19—H19C	109.5	N1—N2—C13	113.47 (16)
C21—C20—N3	115.13 (16)	N4—N3—C20	114.67 (16)
C21—C20—C22	121.64 (16)	N3—N4—C32	112.53 (15)

N1—C1—C2—Cl2	0.6 (2)	N3—C20—C22—C23	−86.1 (2)
C3—C1—C2—Cl2	−174.56 (13)	C21—C20—C22—C27	−81.6 (2)
N1—C1—C2—Cl1	−178.98 (13)	N3—C20—C22—C27	94.7 (2)
C3—C1—C2—Cl1	5.9 (3)	C27—C22—C23—C24	−0.8 (3)
C2—C1—C3—C8	64.6 (2)	C20—C22—C23—C24	179.97 (17)
N1—C1—C3—C8	−110.21 (19)	C22—C23—C24—C25	−0.6 (3)
C2—C1—C3—C4	−119.3 (2)	C23—C24—C25—C26	1.3 (3)
N1—C1—C3—C4	65.9 (2)	C23—C24—C25—C28	−179.07 (17)
C8—C3—C4—C5	1.5 (3)	C24—C25—C26—C27	−0.5 (3)
C1—C3—C4—C5	−174.67 (16)	C28—C25—C26—C27	179.86 (17)
C3—C4—C5—C6	0.1 (3)	C25—C26—C27—C22	−1.0 (3)
C4—C5—C6—C7	−1.4 (3)	C23—C22—C27—C26	1.6 (3)
C4—C5—C6—C9	178.32 (16)	C20—C22—C27—C26	−179.16 (17)
C5—C6—C7—C8	1.1 (3)	C24—C25—C28—C29	6.5 (2)
C9—C6—C7—C8	−178.62 (16)	C26—C25—C28—C29	−173.87 (17)
C6—C7—C8—C3	0.5 (3)	C24—C25—C28—C30	126.39 (19)
C4—C3—C8—C7	−1.8 (3)	C26—C25—C28—C30	−54.0 (2)
C1—C3—C8—C7	174.42 (16)	C24—C25—C28—C31	−114.2 (2)
C7—C6—C9—C12	4.0 (2)	C26—C25—C28—C31	65.5 (2)
C5—C6—C9—C12	−175.72 (17)	C37—C32—C33—C34	0.6 (3)
C7—C6—C9—C11	−116.16 (19)	N4—C32—C33—C34	−178.73 (16)
C5—C6—C9—C11	64.1 (2)	C32—C33—C34—C35	−0.8 (3)
C7—C6—C9—C10	123.96 (18)	C32—C33—C34—C38	178.83 (18)
C5—C6—C9—C10	−55.7 (2)	C33—C34—C35—C36	0.3 (3)
C18—C13—C14—C15	0.8 (3)	C38—C34—C35—C36	−179.32 (19)
N2—C13—C14—C15	−177.87 (16)	C34—C35—C36—C37	0.4 (3)
C13—C14—C15—C16	−0.2 (3)	C35—C36—C37—C32	−0.5 (3)
C13—C14—C15—C19	179.04 (17)	C33—C32—C37—C36	0.0 (3)
C14—C15—C16—C17	−0.6 (3)	N4—C32—C37—C36	179.35 (17)
C19—C15—C16—C17	−179.74 (18)	C2—C1—N1—N2	−177.09 (16)
C15—C16—C17—C18	0.6 (3)	C3—C1—N1—N2	−1.8 (2)
C16—C17—C18—C13	0.0 (3)	C1—N1—N2—C13	176.92 (14)
C14—C13—C18—C17	−0.7 (3)	C14—C13—N2—N1	11.6 (2)
N2—C13—C18—C17	178.04 (16)	C18—C13—N2—N1	−167.08 (15)
N3—C20—C21—Cl3	179.92 (13)	C21—C20—N3—N4	−179.22 (16)
C22—C20—C21—Cl3	−3.5 (3)	C22—C20—N3—N4	4.3 (2)
N3—C20—C21—Cl4	−0.8 (2)	C20—N3—N4—C32	−178.50 (14)
C22—C20—C21—Cl4	175.73 (13)	C33—C32—N4—N3	175.76 (15)
C21—C20—C22—C23	97.6 (2)	C37—C32—N4—N3	−3.6 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the 4-tert-butylphenyl rings [(IVA: C3–C8 and (IVB): C22–C27, respectively]. Cg4 is the centroid of the 3-methylphenyl ring (C32–C37) of molecule (IVB).

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cg4ⁱ	0.95	2.91	3.768 (2)	151
C24—H24···Cg2ⁱⁱ	0.95	2.97	3.824 (2)	150
C29—H29B···Cg1ⁱⁱⁱ	0.98	2.78	3.706 (2)	157

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

Percentage contributions of interatomic contacts to the Hirshfeld surface in the crystal structure top

Contact		Percentage contribution
	(I)	(II)	(III)	(IVA)	(IVB)
H···H	45.3	47.1	43.6	47.0	44.2
Cl···H/H···Cl	22.8	22.2	21.3	20.1	19.8
C···H/H···C	17.5	18.6	17.0	20.7	21.1
N···H/H···N	5.3	5.8	3.7	7.2	8.3
O···H/H···O	–	–	5.1	–	–
Cl···C/C···Cl	3.2	2.8	2.7	2.4	3.3
C···C	2.4	1.2	1.7	0.3	0.3
N···C/C···N	1.5	0.7	1.4	–	–
Cl···N/N···Cl	1.2	0.5	2.9	–	–
Cl···Cl	0.8	1.2	0.6	2.3	3.0

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page