Crystal structures and Hirshfeld surface analyses of the two isotypic compounds (E)-1-(4-bromo­phen­yl)-2-[2,2-di­chloro-1-(4-nitro­phen­yl)ethen­yl]diazene and (E)-1-(4-chloro­phen­yl)-2-[2,2-di­chloro-1-(4-nitro­phen­yl)ethen­yl]diazene

In the crystals of the two isotypic compounds, mol­ecules are linked by weak halogen–halogen (Br...Cl or Cl...Cl) contacts and C—Cl...π inter­actions into sheets lying parallel to the ab plane.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.006 Å
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.033
• wR factor = 0.081
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         N3 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C4 Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6       ..CL2      .       2.92 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          4 Note

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: II


Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         N3 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C4 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00529 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          5 Note

Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   0 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

For both structures, data collection: APEX3 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, 2009).

(E)-1-(4-Bromophenyl)-2-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]diazene (I)

Crystal data

C14H8BrCl2N3O2	Dx = 1.694 Mg m^−3
Mr = 401.04	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 8656 reflections
a = 13.9181 (7) Å	θ = 2.9–27.0°
b = 13.4336 (6) Å	µ = 2.96 mm^−1
c = 8.4080 (4) Å	T = 296 K
V = 1572.05 (13) Å^3	Plate, orange
Z = 4	0.19 × 0.14 × 0.08 mm
F(000) = 792

Data collection

Bruker APEXII CCD diffractometer	2811 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.057
Absorption correction: multi-scan (SADABS; Bruker, 2003)	θmax = 27.1°, θmin = 2.9°
Tmin = 0.608, Tmax = 0.784	h = −17→17
23012 measured reflections	k = −14→17
3429 independent reflections	l = −10→10

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)] = 0.033	w = 1/[σ^2(Fo^2) + (0.0253P)^2 + 0.7719P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.081	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.31 e Å^−3
3429 reflections	Δρmin = −0.50 e Å^−3
200 parameters	Absolute structure: Refined as an inversion twin
1 restraint	Absolute structure parameter: 0.008 (13)

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.

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.4004 (2)	0.5082 (3)	0.5333 (5)	0.0393 (8)
C2	0.3711 (3)	0.4164 (3)	0.4764 (6)	0.0478 (10)
H2	0.309463	0.408665	0.435584	0.057*
C3	0.4334 (3)	0.3360 (3)	0.4803 (6)	0.0545 (11)
H3	0.414420	0.274430	0.440786	0.065*
C4	0.5228 (3)	0.3483 (3)	0.5428 (6)	0.0481 (9)
C5	0.5526 (3)	0.4381 (4)	0.6048 (7)	0.0582 (13)
H5	0.613115	0.444124	0.650896	0.070*
C6	0.4915 (3)	0.5191 (3)	0.5976 (6)	0.0539 (12)
H6	0.511337	0.580727	0.635893	0.065*
C7	0.1912 (2)	0.6569 (2)	0.5030 (5)	0.0378 (8)
C8	0.0975 (3)	0.6351 (3)	0.4948 (6)	0.0477 (10)
C9	0.2272 (3)	0.7616 (2)	0.5010 (5)	0.0345 (7)
C10	0.2658 (3)	0.8034 (3)	0.6372 (5)	0.0437 (9)
H10	0.270870	0.765504	0.729433	0.052*
C11	0.2966 (3)	0.9009 (3)	0.6369 (5)	0.0442 (9)
H11	0.321785	0.929565	0.728509	0.053*
C12	0.2896 (2)	0.9547 (3)	0.4988 (5)	0.0374 (8)
C13	0.2538 (4)	0.9149 (3)	0.3622 (5)	0.0511 (11)
H13	0.250600	0.952658	0.269651	0.061*
C14	0.2221 (3)	0.8170 (3)	0.3637 (5)	0.0491 (10)
H14	0.197279	0.788772	0.271406	0.059*
N1	0.3411 (2)	0.5954 (2)	0.5291 (5)	0.0427 (7)
N2	0.2537 (2)	0.5747 (2)	0.5107 (4)	0.0403 (7)
N3	0.3201 (2)	1.0595 (2)	0.4987 (5)	0.0483 (8)
O1	0.3418 (3)	1.0978 (3)	0.6245 (5)	0.0769 (11)
O2	0.3240 (4)	1.1036 (3)	0.3734 (5)	0.0863 (14)
Cl1	0.05489 (8)	0.51572 (8)	0.4988 (2)	0.0743 (4)
Cl2	0.00955 (8)	0.72322 (9)	0.4870 (2)	0.0713 (4)
Br1	0.60741 (4)	0.23804 (4)	0.54965 (11)	0.0809 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0435 (18)	0.0297 (16)	0.045 (2)	0.0001 (13)	0.0007 (18)	0.0047 (18)
C2	0.045 (2)	0.038 (2)	0.060 (3)	−0.0022 (16)	−0.0050 (19)	−0.007 (2)
C3	0.060 (3)	0.0298 (19)	0.074 (3)	−0.0012 (17)	−0.002 (2)	−0.006 (2)
C4	0.051 (2)	0.0365 (18)	0.057 (3)	0.0094 (15)	0.006 (2)	0.008 (2)
C5	0.043 (2)	0.046 (3)	0.085 (4)	0.0025 (18)	−0.010 (2)	0.002 (2)
C6	0.048 (2)	0.036 (2)	0.077 (3)	−0.0035 (16)	−0.011 (2)	−0.003 (2)
C7	0.0440 (18)	0.0276 (15)	0.042 (2)	0.0021 (14)	0.0025 (17)	0.0016 (16)
C8	0.046 (2)	0.0290 (18)	0.068 (3)	−0.0009 (14)	0.005 (2)	−0.0031 (18)
C9	0.0358 (17)	0.0277 (16)	0.0399 (19)	0.0020 (12)	0.0015 (15)	0.0014 (16)
C10	0.058 (3)	0.035 (2)	0.038 (2)	−0.0045 (18)	−0.0006 (18)	0.0050 (17)
C11	0.056 (2)	0.038 (2)	0.039 (2)	−0.0060 (18)	−0.0025 (18)	−0.0039 (17)
C12	0.0395 (17)	0.0273 (16)	0.045 (2)	0.0006 (13)	0.0045 (17)	0.0003 (17)
C13	0.069 (3)	0.039 (2)	0.046 (2)	−0.004 (2)	−0.006 (2)	0.0098 (18)
C14	0.065 (3)	0.041 (2)	0.041 (2)	−0.007 (2)	−0.009 (2)	0.0037 (18)
N1	0.0446 (16)	0.0288 (14)	0.055 (2)	−0.0015 (11)	0.0023 (16)	0.0018 (15)
N2	0.0437 (15)	0.0280 (13)	0.0493 (19)	0.0012 (12)	0.0009 (15)	0.0017 (14)
N3	0.0564 (19)	0.0302 (16)	0.058 (2)	−0.0046 (14)	0.0018 (19)	0.0012 (18)
O1	0.119 (3)	0.041 (2)	0.071 (2)	−0.022 (2)	−0.004 (2)	−0.0088 (18)
O2	0.142 (4)	0.044 (2)	0.074 (3)	−0.028 (2)	−0.011 (2)	0.0190 (19)
Cl1	0.0508 (6)	0.0360 (5)	0.1362 (12)	−0.0104 (4)	0.0112 (8)	−0.0047 (7)
Cl2	0.0438 (5)	0.0440 (6)	0.1260 (13)	0.0068 (4)	0.0004 (7)	−0.0025 (7)
Br1	0.0781 (3)	0.0554 (3)	0.1093 (5)	0.0306 (2)	0.0097 (4)	0.0087 (4)

Geometric parameters (Å, º)

C1—C2	1.384 (5)	C8—Cl1	1.710 (4)
C1—C6	1.385 (6)	C9—C14	1.376 (6)
C1—N1	1.434 (4)	C9—C10	1.384 (6)
C2—C3	1.386 (6)	C10—C11	1.378 (6)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.361 (6)	C11—C12	1.371 (6)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.377 (6)	C12—C13	1.361 (6)
C4—Br1	1.893 (4)	C12—N3	1.470 (4)
C5—C6	1.384 (6)	C13—C14	1.387 (6)
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—H14	0.9300
C7—C8	1.338 (5)	N1—N2	1.257 (4)
C7—N2	1.407 (4)	N3—O2	1.209 (5)
C7—C9	1.493 (4)	N3—O1	1.214 (5)
C8—Cl2	1.705 (4)
C2—C1—C6	120.0 (4)	C14—C9—C10	119.7 (3)
C2—C1—N1	123.3 (3)	C14—C9—C7	120.1 (3)
C6—C1—N1	116.7 (3)	C10—C9—C7	120.2 (3)
C1—C2—C3	120.1 (4)	C11—C10—C9	120.3 (4)
C1—C2—H2	120.0	C11—C10—H10	119.8
C3—C2—H2	120.0	C9—C10—H10	119.8
C4—C3—C2	119.1 (4)	C12—C11—C10	118.7 (4)
C4—C3—H3	120.4	C12—C11—H11	120.6
C2—C3—H3	120.4	C10—C11—H11	120.6
C3—C4—C5	121.9 (4)	C13—C12—C11	122.2 (3)
C3—C4—Br1	119.0 (3)	C13—C12—N3	118.8 (4)
C5—C4—Br1	119.1 (3)	C11—C12—N3	119.0 (4)
C4—C5—C6	119.1 (4)	C12—C13—C14	118.8 (4)
C4—C5—H5	120.4	C12—C13—H13	120.6
C6—C5—H5	120.4	C14—C13—H13	120.6
C5—C6—C1	119.8 (4)	C9—C14—C13	120.3 (4)
C5—C6—H6	120.1	C9—C14—H14	119.9
C1—C6—H6	120.1	C13—C14—H14	119.9
C8—C7—N2	115.7 (3)	N2—N1—C1	112.3 (3)
C8—C7—C9	122.2 (3)	N1—N2—C7	115.5 (3)
N2—C7—C9	122.2 (3)	O2—N3—O1	122.7 (3)
C7—C8—Cl2	123.3 (3)	O2—N3—C12	118.8 (4)
C7—C8—Cl1	122.8 (3)	O1—N3—C12	118.5 (4)
Cl2—C8—Cl1	113.8 (2)
C6—C1—C2—C3	−1.5 (7)	C7—C9—C10—C11	−178.3 (4)
N1—C1—C2—C3	178.2 (4)	C9—C10—C11—C12	−0.9 (7)
C1—C2—C3—C4	1.0 (7)	C10—C11—C12—C13	−0.4 (7)
C2—C3—C4—C5	1.1 (8)	C10—C11—C12—N3	178.4 (4)
C2—C3—C4—Br1	179.5 (4)	C11—C12—C13—C14	1.0 (7)
C3—C4—C5—C6	−2.7 (8)	N3—C12—C13—C14	−177.9 (4)
Br1—C4—C5—C6	179.0 (4)	C10—C9—C14—C13	−1.2 (7)
C4—C5—C6—C1	2.1 (8)	C7—C9—C14—C13	178.8 (4)
C2—C1—C6—C5	0.0 (7)	C12—C13—C14—C9	−0.1 (7)
N1—C1—C6—C5	−179.8 (4)	C2—C1—N1—N2	18.3 (6)
N2—C7—C8—Cl2	179.2 (3)	C6—C1—N1—N2	−161.9 (4)
C9—C7—C8—Cl2	−1.9 (7)	C1—N1—N2—C7	−179.1 (3)
N2—C7—C8—Cl1	1.8 (6)	C8—C7—N2—N1	−175.4 (4)
C9—C7—C8—Cl1	−179.4 (3)	C9—C7—N2—N1	5.7 (5)
C8—C7—C9—C14	−70.7 (6)	C13—C12—N3—O2	−9.3 (6)
N2—C7—C9—C14	108.1 (5)	C11—C12—N3—O2	171.8 (5)
C8—C7—C9—C10	109.3 (5)	C13—C12—N3—O1	171.9 (5)
N2—C7—C9—C10	−71.9 (5)	C11—C12—N3—O1	−7.0 (6)
C14—C9—C10—C11	1.7 (7)

Hydrogen-bond geometry (Å, º)

Cg2 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cl2^i	0.93	2.92	3.593 (5)	131
C8—Cl2···Cg2^ii	1.71 (1)	3.66 (1)	4.710 (5)	118 (1)

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

(E)-1-(4-Chlorophenyl)-2-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]diazene (II)

Crystal data

C14H8Cl3N3O2	Dx = 1.528 Mg m^−3
Mr = 356.58	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 4206 reflections
a = 13.8689 (7) Å	θ = 2.9–26.4°
b = 13.3674 (7) Å	µ = 0.60 mm^−1
c = 8.3620 (5) Å	T = 296 K
V = 1550.24 (15) Å^3	Prisme, orange
Z = 4	0.17 × 0.14 × 0.07 mm
F(000) = 720

Data collection

Bruker APEXII CCD diffractometer	2547 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.038
Absorption correction: multi-scan (SADABS; Bruker, 2003)	θmax = 26.4°, θmin = 2.9°
Tmin = 0.911, Tmax = 0.946	h = −17→16
11687 measured reflections	k = −16→15
3156 independent reflections	l = −10→10

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)] = 0.037	w = 1/[σ^2(Fo^2) + (0.0419P)^2 + 0.3296P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.091	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.18 e Å^−3
3156 reflections	Δρmin = −0.25 e Å^−3
199 parameters	Absolute structure: Flack x determined using 1011 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013).
1 restraint	Absolute structure parameter: 0.14 (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
C1	0.9044 (2)	0.0035 (2)	0.3115 (4)	0.0400 (8)
C2	0.8753 (3)	−0.0900 (2)	0.3650 (5)	0.0507 (9)
H2	0.813001	−0.099076	0.403349	0.061*
C3	0.9385 (3)	−0.1694 (2)	0.3615 (6)	0.0569 (10)
H3	0.919592	−0.231831	0.399107	0.068*
C4	1.0294 (3)	−0.1555 (3)	0.3023 (5)	0.0532 (10)
C5	1.0584 (3)	−0.0645 (3)	0.2434 (6)	0.0646 (12)
H5	1.119552	−0.056954	0.199546	0.077*
C6	0.9962 (3)	0.0155 (3)	0.2498 (6)	0.0607 (11)
H6	1.015836	0.077758	0.212526	0.073*
C7	0.6941 (2)	0.1515 (2)	0.3415 (4)	0.0376 (7)
C8	0.6001 (2)	0.1294 (2)	0.3491 (6)	0.0480 (8)
C9	0.7299 (2)	0.2569 (2)	0.3447 (5)	0.0364 (6)
C10	0.7644 (3)	0.3003 (3)	0.2053 (4)	0.0464 (9)
H10	0.766518	0.263150	0.111319	0.056*
C11	0.7955 (3)	0.3983 (3)	0.2056 (4)	0.0461 (9)
H11	0.818819	0.427923	0.112661	0.055*
C12	0.7913 (2)	0.4511 (2)	0.3468 (5)	0.0386 (7)
C13	0.7591 (3)	0.4093 (3)	0.4853 (5)	0.0530 (10)
H13	0.757981	0.446192	0.579602	0.064*
C14	0.7280 (3)	0.3110 (3)	0.4834 (5)	0.0507 (10)
H14	0.705639	0.281565	0.577118	0.061*
N1	0.8441 (2)	0.09023 (19)	0.3159 (4)	0.0446 (7)
N2	0.75630 (18)	0.06882 (17)	0.3339 (4)	0.0408 (6)
N3	0.8211 (2)	0.55693 (19)	0.3468 (5)	0.0487 (7)
O1	0.8400 (3)	0.5963 (2)	0.2197 (4)	0.0754 (10)
O2	0.8259 (3)	0.6004 (2)	0.4729 (4)	0.0879 (13)
Cl1	1.10869 (9)	−0.25630 (8)	0.2991 (2)	0.0857 (4)
Cl2	0.55690 (6)	0.00980 (6)	0.3445 (2)	0.0727 (3)
Cl3	0.51218 (7)	0.21874 (7)	0.3590 (2)	0.0751 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0437 (17)	0.0277 (14)	0.048 (2)	−0.0013 (12)	−0.0011 (15)	−0.0030 (14)
C2	0.0481 (18)	0.0381 (16)	0.066 (2)	−0.0012 (14)	0.008 (2)	0.008 (2)
C3	0.062 (2)	0.0325 (16)	0.076 (3)	−0.0010 (15)	0.003 (2)	0.007 (2)
C4	0.053 (2)	0.0379 (18)	0.069 (3)	0.0094 (15)	−0.0048 (18)	−0.0087 (18)
C5	0.046 (2)	0.054 (2)	0.093 (3)	0.0019 (18)	0.012 (2)	0.001 (2)
C6	0.052 (2)	0.039 (2)	0.091 (3)	−0.0075 (17)	0.008 (2)	0.004 (2)
C7	0.0461 (16)	0.0271 (13)	0.0397 (17)	0.0000 (12)	−0.0005 (18)	−0.0028 (17)
C8	0.0471 (17)	0.0284 (14)	0.069 (2)	−0.0008 (13)	−0.004 (2)	0.0006 (19)
C9	0.0361 (14)	0.0294 (13)	0.0437 (17)	0.0023 (11)	−0.0006 (16)	−0.0014 (19)
C10	0.065 (2)	0.037 (2)	0.037 (2)	−0.0058 (17)	0.0002 (18)	−0.0045 (16)
C11	0.061 (2)	0.038 (2)	0.039 (2)	−0.0090 (17)	0.0010 (17)	0.0031 (16)
C12	0.0427 (16)	0.0273 (13)	0.0458 (18)	−0.0003 (12)	−0.0036 (19)	−0.0010 (19)
C13	0.075 (3)	0.039 (2)	0.046 (2)	−0.0076 (19)	0.0109 (19)	−0.0099 (17)
C14	0.073 (3)	0.037 (2)	0.042 (2)	−0.0102 (18)	0.0089 (19)	−0.0038 (17)
N1	0.0476 (15)	0.0295 (12)	0.057 (2)	−0.0009 (11)	0.0003 (14)	−0.0009 (14)
N2	0.0427 (14)	0.0313 (12)	0.0485 (16)	−0.0006 (10)	−0.0025 (15)	−0.0011 (15)
N3	0.0533 (16)	0.0323 (13)	0.061 (2)	−0.0051 (12)	0.001 (2)	0.002 (2)
O1	0.118 (3)	0.0418 (17)	0.067 (2)	−0.0227 (18)	0.0012 (19)	0.0106 (17)
O2	0.149 (4)	0.0453 (19)	0.069 (2)	−0.028 (2)	0.013 (2)	−0.0211 (18)
Cl1	0.0767 (7)	0.0574 (6)	0.1230 (12)	0.0296 (5)	−0.0039 (7)	−0.0084 (7)
Cl2	0.0513 (5)	0.0375 (4)	0.1292 (10)	−0.0109 (3)	−0.0096 (7)	0.0036 (7)
Cl3	0.0456 (5)	0.0450 (5)	0.1348 (11)	0.0067 (4)	−0.0006 (7)	0.0016 (7)

Geometric parameters (Å, º)

C1—C6	1.383 (5)	C8—Cl3	1.708 (3)
C1—C2	1.387 (5)	C9—C14	1.368 (5)
C1—N1	1.430 (4)	C9—C10	1.387 (5)
C2—C3	1.377 (5)	C10—C11	1.379 (5)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.366 (6)	C11—C12	1.377 (5)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.373 (6)	C12—C13	1.362 (6)
C4—Cl1	1.740 (4)	C12—N3	1.473 (4)
C5—C6	1.374 (6)	C13—C14	1.382 (5)
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—H14	0.9300
C7—C8	1.339 (4)	N1—N2	1.259 (4)
C7—N2	1.404 (4)	N3—O2	1.207 (5)
C7—C9	1.493 (4)	N3—O1	1.214 (4)
C8—Cl2	1.708 (3)
C6—C1—C2	119.5 (3)	C14—C9—C10	119.9 (3)
C6—C1—N1	117.0 (3)	C14—C9—C7	120.5 (3)
C2—C1—N1	123.5 (3)	C10—C9—C7	119.6 (3)
C3—C2—C1	120.2 (3)	C11—C10—C9	120.3 (3)
C3—C2—H2	119.9	C11—C10—H10	119.9
C1—C2—H2	119.9	C9—C10—H10	119.9
C4—C3—C2	119.4 (3)	C12—C11—C10	118.4 (3)
C4—C3—H3	120.3	C12—C11—H11	120.8
C2—C3—H3	120.3	C10—C11—H11	120.8
C3—C4—C5	121.3 (3)	C13—C12—C11	122.2 (3)
C3—C4—Cl1	118.9 (3)	C13—C12—N3	119.1 (3)
C5—C4—Cl1	119.7 (3)	C11—C12—N3	118.7 (3)
C4—C5—C6	119.4 (4)	C12—C13—C14	118.9 (3)
C4—C5—H5	120.3	C12—C13—H13	120.6
C6—C5—H5	120.3	C14—C13—H13	120.6
C5—C6—C1	120.2 (4)	C9—C14—C13	120.4 (4)
C5—C6—H6	119.9	C9—C14—H14	119.8
C1—C6—H6	119.9	C13—C14—H14	119.8
C8—C7—N2	115.3 (3)	N2—N1—C1	112.6 (2)
C8—C7—C9	122.1 (3)	N1—N2—C7	114.9 (2)
N2—C7—C9	122.7 (3)	O2—N3—O1	123.0 (3)
C7—C8—Cl2	123.2 (2)	O2—N3—C12	118.5 (3)
C7—C8—Cl3	122.9 (2)	O1—N3—C12	118.4 (3)
Cl2—C8—Cl3	113.90 (19)
C6—C1—C2—C3	2.1 (7)	C7—C9—C10—C11	178.5 (3)
N1—C1—C2—C3	−178.0 (4)	C9—C10—C11—C12	0.0 (6)
C1—C2—C3—C4	−1.1 (7)	C10—C11—C12—C13	1.1 (6)
C2—C3—C4—C5	−1.3 (7)	C10—C11—C12—N3	−177.8 (3)
C2—C3—C4—Cl1	179.8 (3)	C11—C12—C13—C14	−1.1 (6)
C3—C4—C5—C6	2.6 (8)	N3—C12—C13—C14	177.7 (3)
Cl1—C4—C5—C6	−178.5 (4)	C10—C9—C14—C13	0.9 (6)
C4—C5—C6—C1	−1.6 (8)	C7—C9—C14—C13	−178.5 (4)
C2—C1—C6—C5	−0.8 (7)	C12—C13—C14—C9	0.1 (6)
N1—C1—C6—C5	179.4 (4)	C6—C1—N1—N2	162.9 (4)
N2—C7—C8—Cl2	−1.8 (6)	C2—C1—N1—N2	−17.0 (5)
C9—C7—C8—Cl2	179.6 (3)	C1—N1—N2—C7	179.0 (3)
N2—C7—C8—Cl3	−179.9 (3)	C8—C7—N2—N1	175.4 (4)
C9—C7—C8—Cl3	1.4 (6)	C9—C7—N2—N1	−5.9 (5)
C8—C7—C9—C14	73.1 (5)	C13—C12—N3—O2	7.8 (5)
N2—C7—C9—C14	−105.4 (4)	C11—C12—N3—O2	−173.3 (4)
C8—C7—C9—C10	−106.3 (5)	C13—C12—N3—O1	−172.4 (4)
N2—C7—C9—C10	75.2 (5)	C11—C12—N3—O1	6.5 (5)
C14—C9—C10—C11	−0.9 (6)

Hydrogen-bond geometry (Å, º)

Cg2 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—Cl3···Cg2^i	1.71 (1)	3.62 (1)	4.703 (3)	120 (1)

Symmetry code: (i) x−1/2, −y+1/2, z.