(E,E)-N,N′-Bis(4-chloro­phen­yl)ethyl­enediamine

There are two crystallographically independent mol­ecules in the asymmetric unit of the title compound, C₁₆H₁₄Cl₂N₂, each possessing an E configuration about each azomethine C=N bond. The mol­ecules also adopt a staggered conformation about the ethyl­ene bridge. Weak C—H...π inter­actions link the mol­ecules into ribbons along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.028
• wR factor = 0.074
• Data-to-parameter ratio = 22.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          8

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           30.00
           From the CIF: _reflns_number_total               8157
           Count of symmetry unique reflns         4097
           Completeness (_total/calc)            199.10%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      4060
           Fraction of Friedel pairs measured     0.991
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

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

Author Response: H. Bahron, K. Kassim, S.R. S. Omar and S. H. Rashid are involved in the synthesis. H. K. Fun and S. Chantrapromma are involved in X-ray structure determination. All are involved in manuscript preparation.

   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: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

(E,E)—N,N'-Bis(4-chlorophenyl)ethylenediamine

Crystal data

C16H14Cl2N2	F(000) = 1264
Mr = 305.19	Dx = 1.443 Mg m^−3
Monoclinic, Cc	Melting point: 398-399 K K
Hall symbol: C -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 10.1657 (3) Å	Cell parameters from 4019 reflections
b = 10.3602 (3) Å	θ = 2.8–30.0°
c = 26.6975 (7) Å	µ = 0.45 mm^−1
β = 92.115 (2)°	T = 100 K
V = 2809.83 (14) Å^3	Plate, colourless
Z = 8	0.59 × 0.52 × 0.15 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	8157 independent reflections
Radiation source: fine-focus sealed tube	7884 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 8.33 pixels mm^-1	θmax = 30.0°, θmin = 2.8°
ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −14→14
Tmin = 0.775, Tmax = 0.935	l = −37→37
26237 measured reflections

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)] = 0.028	H-atom parameters constrained
wR(F^2) = 0.074	w = 1/[σ^2(Fo^2) + (0.0418P)^2 + 1.1133P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
8157 reflections	Δρmax = 0.35 e Å^−3
362 parameters	Δρmin = −0.19 e Å^−3
2 restraints	Absolute structure: Flack (1983); 4063 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.15 (3)

Special details

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Cl1A	1.30083 (3)	−0.39543 (4)	0.390723 (13)	0.01980 (8)
Cl2A	0.45186 (3)	0.63418 (4)	−0.008612 (13)	0.02088 (8)
N1A	0.99788 (12)	0.02393 (13)	0.22900 (5)	0.0162 (2)
N2A	0.74738 (12)	0.21577 (13)	0.15531 (5)	0.0166 (2)
C1A	1.13974 (14)	−0.18687 (14)	0.27848 (5)	0.0156 (3)
H1A	1.1315	−0.1920	0.2437	0.019*
C2A	1.20263 (13)	−0.28529 (15)	0.30533 (5)	0.0158 (3)
H2A	1.2353	−0.3569	0.2889	0.019*
C3A	1.21603 (13)	−0.27495 (14)	0.35728 (5)	0.0147 (3)
C4A	1.16616 (14)	−0.17058 (16)	0.38299 (6)	0.0173 (3)
H4A	1.1752	−0.1657	0.4177	0.021*
C5A	1.10241 (13)	−0.07358 (15)	0.35571 (5)	0.0159 (3)
H5A	1.0682	−0.0030	0.3724	0.019*
C6A	1.08892 (13)	−0.08059 (15)	0.30321 (5)	0.0140 (3)
C7A	1.02248 (13)	0.02653 (14)	0.27617 (5)	0.0143 (2)
H7A	0.9976	0.0988	0.2942	0.017*
C8A	0.93636 (15)	0.13902 (15)	0.20657 (6)	0.0162 (3)
H8AA	0.9963	0.1793	0.1839	0.019*
H8AB	0.9172	0.2007	0.2326	0.019*
C9A	0.80925 (15)	0.10152 (14)	0.17803 (6)	0.0161 (3)
H9AA	0.8285	0.0394	0.1521	0.019*
H9AB	0.7493	0.0615	0.2008	0.019*
C10A	0.72265 (13)	0.21206 (14)	0.10828 (5)	0.0148 (2)
H10A	0.7476	0.1393	0.0906	0.018*
C11A	0.65629 (13)	0.31799 (14)	0.08074 (5)	0.0142 (3)
C12A	0.60404 (14)	0.42493 (15)	0.10553 (5)	0.0156 (3)
H12A	0.6104	0.4299	0.1403	0.019*
C13A	0.54272 (14)	0.52351 (14)	0.07795 (5)	0.0156 (3)
H13A	0.5097	0.5955	0.0941	0.019*
C14A	0.53139 (13)	0.51294 (14)	0.02589 (6)	0.0153 (3)
C15A	0.58157 (14)	0.40859 (15)	0.00088 (6)	0.0181 (3)
H15A	0.5735	0.4033	−0.0339	0.022*
C16A	0.64452 (14)	0.31141 (15)	0.02857 (5)	0.0174 (3)
H16A	0.6793	0.2409	0.0120	0.021*
Cl1B	1.34835 (3)	0.16946 (4)	0.395401 (14)	0.02254 (8)
Cl2B	0.38351 (3)	1.08483 (4)	−0.012081 (13)	0.02106 (8)
N1B	0.96239 (12)	0.49852 (13)	0.22611 (5)	0.0167 (2)
N2B	0.77550 (12)	0.75132 (13)	0.15337 (5)	0.0175 (2)
C1B	1.16767 (13)	0.35206 (15)	0.28021 (6)	0.0156 (3)
H1B	1.1820	0.3669	0.2465	0.019*
C2B	1.25973 (14)	0.28319 (15)	0.30931 (6)	0.0170 (3)
H2B	1.3364	0.2530	0.2954	0.020*
C3B	1.23605 (14)	0.26004 (14)	0.35936 (6)	0.0162 (3)
C4B	1.12324 (15)	0.30489 (15)	0.38143 (6)	0.0179 (3)
H4B	1.1088	0.2884	0.4150	0.021*
C5B	1.03256 (13)	0.37485 (15)	0.35233 (5)	0.0162 (3)
H5B	0.9569	0.4061	0.3667	0.019*
C6B	1.05354 (13)	0.39906 (14)	0.30153 (5)	0.0141 (3)
C7B	0.95106 (13)	0.46966 (14)	0.27201 (6)	0.0156 (3)
H7B	0.8748	0.4941	0.2877	0.019*
C8B	0.84906 (14)	0.56109 (16)	0.20125 (6)	0.0178 (3)
H8BA	0.7820	0.5769	0.2254	0.021*
H8BB	0.8120	0.5046	0.1754	0.021*
C9B	0.88971 (14)	0.68835 (15)	0.17783 (6)	0.0180 (3)
H9BA	0.9275	0.7446	0.2036	0.022*
H9BB	0.9561	0.6725	0.1534	0.022*
C10B	0.78503 (13)	0.78021 (14)	0.10736 (5)	0.0156 (3)
H10B	0.8605	0.7555	0.0912	0.019*
C11B	0.68170 (13)	0.85122 (14)	0.07841 (5)	0.0144 (3)
C12B	0.56647 (14)	0.89420 (14)	0.10058 (5)	0.0156 (3)
H12B	0.5525	0.8755	0.1340	0.019*
C13B	0.47341 (13)	0.96451 (15)	0.07273 (5)	0.0158 (3)
H13B	0.3965	0.9924	0.0871	0.019*
C14B	0.49732 (14)	0.99275 (14)	0.02260 (6)	0.0154 (3)
C15B	0.60973 (14)	0.95143 (14)	0.00004 (5)	0.0165 (3)
H15B	0.6236	0.9705	−0.0334	0.020*
C16B	0.70210 (13)	0.88045 (14)	0.02844 (5)	0.0162 (2)
H16B	0.7785	0.8522	0.0137	0.019*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1A	0.01867 (15)	0.02024 (16)	0.02050 (16)	0.00305 (13)	0.00104 (12)	0.00623 (13)
Cl2A	0.02261 (15)	0.01861 (16)	0.02140 (16)	0.00435 (14)	0.00053 (12)	0.00593 (14)
N1A	0.0157 (5)	0.0166 (6)	0.0162 (6)	0.0015 (4)	−0.0007 (4)	0.0008 (5)
N2A	0.0166 (5)	0.0150 (6)	0.0180 (6)	0.0016 (5)	−0.0010 (4)	−0.0003 (5)
C1A	0.0155 (6)	0.0180 (7)	0.0133 (6)	−0.0010 (5)	−0.0001 (5)	−0.0008 (5)
C2A	0.0148 (6)	0.0168 (6)	0.0158 (6)	0.0005 (5)	0.0015 (5)	−0.0011 (5)
C3A	0.0116 (5)	0.0171 (7)	0.0152 (6)	−0.0007 (5)	−0.0008 (5)	0.0026 (5)
C4A	0.0144 (5)	0.0235 (7)	0.0141 (6)	−0.0003 (5)	−0.0010 (5)	−0.0001 (6)
C5A	0.0154 (6)	0.0180 (7)	0.0144 (6)	0.0024 (5)	0.0005 (5)	−0.0034 (5)
C6A	0.0115 (5)	0.0156 (6)	0.0147 (6)	−0.0012 (5)	−0.0002 (4)	−0.0001 (5)
C7A	0.0122 (5)	0.0141 (6)	0.0168 (6)	−0.0006 (5)	0.0008 (5)	−0.0015 (5)
C8A	0.0175 (6)	0.0156 (6)	0.0153 (6)	−0.0001 (5)	−0.0012 (5)	0.0006 (5)
C9A	0.0173 (6)	0.0141 (6)	0.0167 (6)	−0.0002 (5)	−0.0008 (5)	0.0015 (5)
C10A	0.0134 (5)	0.0143 (6)	0.0165 (6)	0.0001 (5)	0.0003 (5)	−0.0004 (5)
C11A	0.0123 (5)	0.0139 (6)	0.0164 (6)	−0.0015 (5)	−0.0004 (5)	−0.0003 (5)
C12A	0.0151 (6)	0.0181 (7)	0.0136 (6)	−0.0006 (5)	−0.0010 (5)	−0.0017 (5)
C13A	0.0161 (6)	0.0147 (6)	0.0159 (6)	0.0009 (5)	0.0010 (5)	−0.0024 (5)
C14A	0.0143 (6)	0.0144 (6)	0.0172 (7)	0.0007 (5)	0.0000 (5)	0.0038 (5)
C15A	0.0211 (6)	0.0201 (7)	0.0130 (6)	0.0010 (6)	0.0005 (5)	0.0007 (5)
C16A	0.0196 (6)	0.0169 (7)	0.0156 (6)	0.0022 (5)	0.0002 (5)	−0.0019 (5)
Cl1B	0.02528 (16)	0.01895 (16)	0.02265 (17)	0.00315 (14)	−0.00919 (13)	0.00050 (13)
Cl2B	0.01999 (15)	0.02160 (16)	0.02118 (16)	0.00490 (13)	−0.00484 (12)	0.00091 (13)
N1B	0.0158 (5)	0.0167 (6)	0.0175 (6)	0.0016 (5)	−0.0013 (4)	0.0021 (5)
N2B	0.0148 (5)	0.0175 (6)	0.0201 (6)	0.0027 (5)	−0.0015 (4)	0.0016 (5)
C1B	0.0162 (6)	0.0161 (6)	0.0146 (6)	0.0004 (5)	0.0015 (5)	0.0021 (5)
C2B	0.0149 (6)	0.0163 (7)	0.0199 (7)	0.0005 (5)	0.0015 (5)	−0.0007 (5)
C3B	0.0182 (6)	0.0125 (6)	0.0174 (7)	−0.0004 (5)	−0.0051 (5)	0.0008 (5)
C4B	0.0224 (6)	0.0158 (6)	0.0154 (6)	−0.0011 (6)	0.0002 (5)	0.0010 (5)
C5B	0.0174 (6)	0.0152 (6)	0.0163 (6)	−0.0004 (5)	0.0027 (5)	−0.0007 (5)
C6B	0.0147 (6)	0.0120 (6)	0.0155 (6)	−0.0014 (5)	−0.0017 (5)	0.0015 (5)
C7B	0.0136 (5)	0.0136 (6)	0.0197 (6)	0.0000 (5)	−0.0003 (5)	−0.0002 (5)
C8B	0.0144 (6)	0.0197 (7)	0.0191 (6)	0.0005 (5)	−0.0019 (5)	0.0028 (6)
C9B	0.0144 (6)	0.0208 (7)	0.0184 (7)	0.0009 (5)	−0.0028 (5)	0.0011 (5)
C10B	0.0138 (5)	0.0140 (6)	0.0188 (6)	0.0009 (5)	−0.0011 (5)	−0.0011 (5)
C11B	0.0135 (5)	0.0120 (6)	0.0176 (7)	−0.0004 (5)	−0.0001 (5)	−0.0006 (5)
C12B	0.0160 (6)	0.0159 (7)	0.0147 (6)	−0.0016 (5)	0.0000 (5)	0.0014 (5)
C13B	0.0138 (5)	0.0167 (6)	0.0171 (6)	0.0008 (5)	0.0012 (5)	−0.0008 (5)
C14B	0.0161 (6)	0.0127 (6)	0.0171 (6)	0.0001 (5)	−0.0037 (5)	0.0003 (5)
C15B	0.0194 (6)	0.0163 (6)	0.0137 (6)	0.0007 (5)	0.0005 (5)	0.0002 (5)
C16B	0.0155 (5)	0.0149 (6)	0.0183 (6)	0.0010 (5)	0.0027 (5)	−0.0009 (5)

Geometric parameters (Å, º)

Cl1A—C3A	1.7439 (14)	Cl1B—C3B	1.7403 (15)
Cl2A—C14A	1.7392 (15)	Cl2B—C14B	1.7398 (14)
N1A—C7A	1.2751 (19)	N1B—C7B	1.271 (2)
N1A—C8A	1.464 (2)	N1B—C8B	1.4598 (18)
N2A—C10A	1.2721 (19)	N2B—C10B	1.271 (2)
N2A—C9A	1.4617 (19)	N2B—C9B	1.4643 (18)
C1A—C2A	1.389 (2)	C1B—C2B	1.391 (2)
C1A—C6A	1.393 (2)	C1B—C6B	1.399 (2)
C1A—H1A	0.93	C1B—H1B	0.93
C2A—C3A	1.3928 (19)	C2B—C3B	1.387 (2)
C2A—H2A	0.93	C2B—H2B	0.93
C3A—C4A	1.387 (2)	C3B—C4B	1.389 (2)
C4A—C5A	1.388 (2)	C4B—C5B	1.388 (2)
C4A—H4A	0.93	C4B—H4B	0.93
C5A—C6A	1.4052 (19)	C5B—C6B	1.4032 (19)
C5A—H5A	0.93	C5B—H5B	0.93
C6A—C7A	1.474 (2)	C6B—C7B	1.4767 (19)
C7A—H7A	0.93	C7B—H7B	0.93
C8A—C9A	1.5260 (16)	C8B—C9B	1.5229 (18)
C8A—H8AA	0.97	C8B—H8BA	0.97
C8A—H8AB	0.97	C8B—H8BB	0.97
C9A—H9AA	0.97	C9B—H9BA	0.97
C9A—H9AB	0.97	C9B—H9BB	0.97
C10A—C11A	1.4709 (19)	C10B—C11B	1.4772 (19)
C10A—H10A	0.93	C10B—H10B	0.93
C11A—C16A	1.395 (2)	C11B—C16B	1.391 (2)
C11A—C12A	1.405 (2)	C11B—C12B	1.404 (2)
C12A—C13A	1.393 (2)	C12B—C13B	1.3880 (19)
C12A—H12A	0.93	C12B—H12B	0.93
C13A—C14A	1.395 (2)	C13B—C14B	1.400 (2)
C13A—H13A	0.93	C13B—H13B	0.93
C14A—C15A	1.378 (2)	C14B—C15B	1.379 (2)
C15A—C16A	1.391 (2)	C15B—C16B	1.394 (2)
C15A—H15A	0.93	C15B—H15B	0.93
C16A—H16A	0.93	C16B—H16B	0.93
C7A—N1A—C8A	116.87 (13)	C7B—N1B—C8B	116.41 (13)
C10A—N2A—C9A	116.84 (13)	C10B—N2B—C9B	116.63 (13)
C2A—C1A—C6A	120.49 (14)	C2B—C1B—C6B	120.16 (14)
C2A—C1A—H1A	119.8	C2B—C1B—H1B	119.9
C6A—C1A—H1A	119.8	C6B—C1B—H1B	119.9
C1A—C2A—C3A	118.94 (13)	C3B—C2B—C1B	119.32 (13)
C1A—C2A—H2A	120.5	C3B—C2B—H2B	120.3
C3A—C2A—H2A	120.5	C1B—C2B—H2B	120.3
C4A—C3A—C2A	121.93 (13)	C2B—C3B—C4B	121.76 (13)
C4A—C3A—Cl1A	119.17 (11)	C2B—C3B—Cl1B	119.49 (12)
C2A—C3A—Cl1A	118.89 (11)	C4B—C3B—Cl1B	118.74 (12)
C3A—C4A—C5A	118.49 (13)	C5B—C4B—C3B	118.61 (14)
C3A—C4A—H4A	120.8	C5B—C4B—H4B	120.7
C5A—C4A—H4A	120.8	C3B—C4B—H4B	120.7
C4A—C5A—C6A	120.84 (14)	C4B—C5B—C6B	120.87 (13)
C4A—C5A—H5A	119.6	C4B—C5B—H5B	119.6
C6A—C5A—H5A	119.6	C6B—C5B—H5B	119.6
C1A—C6A—C5A	119.30 (13)	C1B—C6B—C5B	119.27 (13)
C1A—C6A—C7A	122.29 (13)	C1B—C6B—C7B	122.33 (13)
C5A—C6A—C7A	118.40 (13)	C5B—C6B—C7B	118.36 (13)
N1A—C7A—C6A	122.51 (13)	N1B—C7B—C6B	122.95 (13)
N1A—C7A—H7A	118.7	N1B—C7B—H7B	118.5
C6A—C7A—H7A	118.7	C6B—C7B—H7B	118.5
N1A—C8A—C9A	109.75 (11)	N1B—C8B—C9B	110.46 (11)
N1A—C8A—H8AA	109.7	N1B—C8B—H8BA	109.6
C9A—C8A—H8AA	109.7	C9B—C8B—H8BA	109.6
N1A—C8A—H8AB	109.7	N1B—C8B—H8BB	109.6
C9A—C8A—H8AB	109.7	C9B—C8B—H8BB	109.6
H8AA—C8A—H8AB	108.2	H8BA—C8B—H8BB	108.1
N2A—C9A—C8A	110.15 (11)	N2B—C9B—C8B	110.25 (11)
N2A—C9A—H9AA	109.6	N2B—C9B—H9BA	109.6
C8A—C9A—H9AA	109.6	C8B—C9B—H9BA	109.6
N2A—C9A—H9AB	109.6	N2B—C9B—H9BB	109.6
C8A—C9A—H9AB	109.6	C8B—C9B—H9BB	109.6
H9AA—C9A—H9AB	108.1	H9BA—C9B—H9BB	108.1
N2A—C10A—C11A	122.76 (13)	N2B—C10B—C11B	123.00 (13)
N2A—C10A—H10A	118.6	N2B—C10B—H10B	118.5
C11A—C10A—H10A	118.6	C11B—C10B—H10B	118.5
C16A—C11A—C12A	119.27 (13)	C16B—C11B—C12B	119.43 (12)
C16A—C11A—C10A	118.90 (13)	C16B—C11B—C10B	118.81 (13)
C12A—C11A—C10A	121.83 (13)	C12B—C11B—C10B	121.71 (13)
C13A—C12A—C11A	119.92 (13)	C13B—C12B—C11B	120.21 (13)
C13A—C12A—H12A	120.0	C13B—C12B—H12B	119.9
C11A—C12A—H12A	120.0	C11B—C12B—H12B	119.9
C12A—C13A—C14A	119.22 (13)	C12B—C13B—C14B	118.88 (13)
C12A—C13A—H13A	120.4	C12B—C13B—H13B	120.6
C14A—C13A—H13A	120.4	C14B—C13B—H13B	120.6
C15A—C14A—C13A	121.72 (13)	C15B—C14B—C13B	121.90 (13)
C15A—C14A—Cl2A	118.88 (11)	C15B—C14B—Cl2B	118.89 (12)
C13A—C14A—Cl2A	119.39 (11)	C13B—C14B—Cl2B	119.20 (11)
C14A—C15A—C16A	118.79 (14)	C14B—C15B—C16B	118.58 (13)
C14A—C15A—H15A	120.6	C14B—C15B—H15B	120.7
C16A—C15A—H15A	120.6	C16B—C15B—H15B	120.7
C15A—C16A—C11A	121.06 (14)	C11B—C16B—C15B	121.00 (13)
C15A—C16A—H16A	119.5	C11B—C16B—H16B	119.5
C11A—C16A—H16A	119.5	C15B—C16B—H16B	119.5
C6A—C1A—C2A—C3A	−1.1 (2)	C6B—C1B—C2B—C3B	1.0 (2)
C1A—C2A—C3A—C4A	1.3 (2)	C1B—C2B—C3B—C4B	−0.6 (2)
C1A—C2A—C3A—Cl1A	−177.45 (11)	C1B—C2B—C3B—Cl1B	177.93 (11)
C2A—C3A—C4A—C5A	−0.7 (2)	C2B—C3B—C4B—C5B	−0.1 (2)
Cl1A—C3A—C4A—C5A	178.07 (11)	Cl1B—C3B—C4B—C5B	−178.70 (12)
C3A—C4A—C5A—C6A	−0.2 (2)	C3B—C4B—C5B—C6B	0.5 (2)
C2A—C1A—C6A—C5A	0.3 (2)	C2B—C1B—C6B—C5B	−0.6 (2)
C2A—C1A—C6A—C7A	179.46 (13)	C2B—C1B—C6B—C7B	−178.33 (14)
C4A—C5A—C6A—C1A	0.4 (2)	C4B—C5B—C6B—C1B	−0.1 (2)
C4A—C5A—C6A—C7A	−178.85 (13)	C4B—C5B—C6B—C7B	177.65 (13)
C8A—N1A—C7A—C6A	−177.52 (12)	C8B—N1B—C7B—C6B	176.18 (13)
C1A—C6A—C7A—N1A	5.8 (2)	C1B—C6B—C7B—N1B	−3.8 (2)
C5A—C6A—C7A—N1A	−174.98 (13)	C5B—C6B—C7B—N1B	178.45 (14)
C7A—N1A—C8A—C9A	−124.66 (13)	C7B—N1B—C8B—C9B	124.88 (14)
C10A—N2A—C9A—C8A	124.79 (13)	C10B—N2B—C9B—C8B	−124.65 (14)
N1A—C8A—C9A—N2A	−179.75 (14)	N1B—C8B—C9B—N2B	−179.45 (14)
C9A—N2A—C10A—C11A	177.70 (12)	C9B—N2B—C10B—C11B	−176.06 (13)
N2A—C10A—C11A—C16A	173.82 (13)	N2B—C10B—C11B—C16B	178.86 (14)
N2A—C10A—C11A—C12A	−6.5 (2)	N2B—C10B—C11B—C12B	1.5 (2)
C16A—C11A—C12A—C13A	−0.8 (2)	C16B—C11B—C12B—C13B	0.4 (2)
C10A—C11A—C12A—C13A	179.58 (13)	C10B—C11B—C12B—C13B	177.79 (14)
C11A—C12A—C13A—C14A	1.5 (2)	C11B—C12B—C13B—C14B	−0.7 (2)
C12A—C13A—C14A—C15A	−1.3 (2)	C12B—C13B—C14B—C15B	0.8 (2)
C12A—C13A—C14A—Cl2A	178.66 (11)	C12B—C13B—C14B—Cl2B	−178.14 (11)
C13A—C14A—C15A—C16A	0.3 (2)	C13B—C14B—C15B—C16B	−0.5 (2)
Cl2A—C14A—C15A—C16A	−179.66 (12)	Cl2B—C14B—C15B—C16B	178.39 (11)
C14A—C15A—C16A—C11A	0.5 (2)	C12B—C11B—C16B—C15B	−0.2 (2)
C12A—C11A—C16A—C15A	−0.3 (2)	C10B—C11B—C16B—C15B	−177.61 (13)
C10A—C11A—C16A—C15A	179.42 (13)	C14B—C15B—C16B—C11B	0.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7A—H7A···Cg1	0.93	2.96	3.656 (2)	132
C10A—H10A···Cg2^i	0.93	2.95	3.618 (2)	130

Symmetry code: (i) x, y−1, z.