(E,E)-1,1′-[1,2-Bis(4-chloro­phen­yl)ethane-1,2-di­yl]bis­(phenyl­diazene) revisited: threefold configurational disorder of (S,S), (R,R) and (S,R) isomers, a detailed critique

Crystal structures described as concomitant triclinic (I) and mono­clinic (II) polymorphs of meso-(E,E)-1,1′-[1,2-bis­(4-chloro­phen­yl)ethane-1,2-di­yl]bis­(phenyl­diazene) [Mohamed et al. (2016). Acta Cryst. C72, 57–62] have been re-investigated. The published model for II was distorted due to forcing the symmetry of space group C2/c on an incom­plete structure model. It is shown here to be a likely three-com­ponent superposition of S,S and R,R enanti­omers with a lesser amount of the meso form. A detailed analysis of how the improbable distortion in the published model aroused suspicion and the subsequent construction of undistorted chemically and crystallographically plausible alternatives having the symmetry of Cc and C2/c is presented. For the sake of com­pleteness, an improved model for the triclinic P structure of the meso isomer I, revised to include a minor disorder com­ponent, is also given.

Computing details

Data collection: CrystalClear-SM Expert (Rigaku, 2012) for (I). For all structures, cell refinement: CrystalClear-SM Expert (Rigaku, 2012); data reduction: CrystalClear-SM Expert (Rigaku, 2012); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2019 (Sheldrick, 2015b). Molecular graphics: XP in SHELXTL (Sheldrick, 2008) for (I); ShelXle (Hübschle et al., 2011) for (IIc), (IId). Software used to prepare material for publication: SHELXL2019 (Sheldrick, 2015b) and publCIF (Westrip, 2010) for (I); SHELXL2019 (Sheldrick, 2015b) for (IIc), (IId).

1,1'-[1,2-Bis(4-chlorophenyl)ethane-1,2-diyl]bis(phenyldiazene) (I)

Crystal data

C26H20Cl2N4	Z = 1
Mr = 459.36	F(000) = 238
Triclinic, P1	Dx = 1.331 Mg m^−3
a = 6.1037 (4) Å	Mo Kα radiation, λ = 0.71075 Å
b = 9.3345 (7) Å	Cell parameters from 3602 reflections
c = 10.4146 (7) Å	θ = 2.2–27.5°
α = 83.039 (1)°	µ = 0.31 mm^−1
β = 77.139 (9)°	T = 100 K
γ = 85.055 (1)°	Plate, yellow
V = 573.15 (7) Å^3	0.19 × 0.08 × 0.01 mm

Data collection

Rigaku AFC12 diffractometer	2029 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm^-1	Rint = 0.037
profile data from ω–scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012)	h = −5→7
Tmin = 0.710, Tmax = 0.997	k = −12→12
6621 measured reflections	l = −11→13
2602 independent reflections

Refinement

Refinement on F^2	684 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.152	w = 1/[σ^2(Fo^2) + (0.0795P)^2 + 0.2745P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
2602 reflections	Δρmax = 0.50 e Å^−3
254 parameters	Δρmin = −0.37 e Å^−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	Occ. (<1)
Cl1	1.07708 (11)	1.04684 (7)	0.26667 (8)	0.0519 (3)	0.938 (2)
N1	0.5280 (3)	0.4524 (2)	0.3295 (2)	0.0309 (4)	0.938 (2)
N2	0.3712 (3)	0.4576 (2)	0.27056 (19)	0.0317 (4)	0.938 (2)
C1	0.4759 (4)	0.5470 (3)	0.4378 (2)	0.0309 (5)	0.938 (2)
H1	0.314157	0.583255	0.453113	0.037*	0.938 (2)
C2	0.6281 (4)	0.6732 (3)	0.3980 (2)	0.0298 (5)	0.938 (2)
C3	0.8602 (3)	0.6475 (2)	0.3523 (2)	0.0313 (5)	0.938 (2)
H3	0.923011	0.550890	0.349967	0.038*	0.938 (2)
C4	0.9987 (4)	0.7610 (3)	0.3105 (3)	0.0358 (5)	0.938 (2)
H4	1.155742	0.743237	0.278198	0.043*	0.938 (2)
C5	0.9044 (4)	0.9025 (2)	0.3166 (2)	0.0363 (5)	0.938 (2)
C6	0.6750 (4)	0.9302 (2)	0.3616 (2)	0.0364 (5)	0.938 (2)
H6	0.612603	1.026823	0.365184	0.044*	0.938 (2)
C7	0.5376 (4)	0.8147 (2)	0.4014 (2)	0.0330 (5)	0.938 (2)
H7	0.379998	0.832783	0.431207	0.040*	0.938 (2)
C8	0.4142 (4)	0.3686 (2)	0.1629 (2)	0.0332 (5)	0.938 (2)
C9	0.2481 (4)	0.3793 (3)	0.0901 (2)	0.0406 (6)	0.938 (2)
H9	0.118460	0.442967	0.111913	0.049*	0.938 (2)
C10	0.2720 (5)	0.2961 (3)	−0.0151 (2)	0.0475 (7)	0.938 (2)
H10	0.158512	0.303624	−0.065363	0.057*	0.938 (2)
C11	0.4607 (14)	0.2024 (10)	−0.0472 (9)	0.0492 (14)	0.938 (2)
H11	0.477227	0.145688	−0.119018	0.059*	0.938 (2)
C12	0.6254 (5)	0.1928 (3)	0.0277 (3)	0.0470 (6)	0.938 (2)
H12	0.754273	0.128306	0.006740	0.056*	0.938 (2)
C13	0.6050 (4)	0.2752 (3)	0.1315 (2)	0.0371 (6)	0.938 (2)
H13	0.719456	0.268545	0.181043	0.045*	0.938 (2)
Cl1'	0.442 (6)	0.220 (5)	−0.034 (4)	0.061 (7)	0.062 (2)
N1'	0.679 (4)	0.638 (2)	0.3877 (12)	0.031 (4)	0.062 (2)
N2'	0.611 (3)	0.764 (2)	0.4111 (16)	0.033 (4)	0.062 (2)
C1'	0.497 (5)	0.537 (2)	0.4297 (11)	0.0309 (5)	0.062 (2)
H1'	0.355782	0.601310	0.442909	0.037*	0.062 (2)
C2'	0.484 (4)	0.456 (2)	0.313 (2)	0.032 (3)	0.062 (2)
C3'	0.298 (4)	0.481 (3)	0.255 (2)	0.034 (4)	0.062 (2)
H3'	0.179041	0.548436	0.288600	0.041*	0.062 (2)
C4'	0.286 (4)	0.409 (3)	0.148 (2)	0.039 (4)	0.062 (2)
H4'	0.158839	0.425812	0.108868	0.047*	0.062 (2)
C5'	0.460 (4)	0.310 (3)	0.099 (2)	0.043 (3)	0.062 (2)
C6'	0.646 (4)	0.285 (3)	0.157 (2)	0.041 (4)	0.062 (2)
H6'	0.765156	0.218053	0.123801	0.049*	0.062 (2)
C7'	0.658 (4)	0.358 (2)	0.264 (2)	0.034 (4)	0.062 (2)
H7'	0.785362	0.340677	0.303533	0.041*	0.062 (2)
C8'	0.790 (3)	0.8627 (19)	0.3698 (16)	0.044 (4)	0.062 (2)
C9'	0.994 (4)	0.7935 (18)	0.314 (2)	0.045 (5)	0.062 (2)
H9'	1.003033	0.692531	0.307450	0.054*	0.062 (2)
C10'	1.184 (3)	0.872 (3)	0.269 (3)	0.055 (5)	0.062 (2)
H10'	1.323871	0.824792	0.231450	0.066*	0.062 (2)
C11'	1.171 (4)	1.020 (3)	0.280 (3)	0.0519 (3)	0.062 (2)
H11'	1.301252	1.073505	0.248647	0.062*	0.062 (2)
C12'	0.967 (4)	1.0890 (18)	0.335 (3)	0.049 (5)	0.062 (2)
H12'	0.957793	1.189960	0.341843	0.059*	0.062 (2)
C13'	0.776 (3)	1.010 (2)	0.380 (3)	0.056 (5)	0.062 (2)
H13'	0.636951	1.057702	0.417843	0.068*	0.062 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0402 (4)	0.0351 (3)	0.0755 (5)	−0.0120 (3)	−0.0073 (3)	0.0114 (3)
N1	0.0311 (10)	0.0325 (9)	0.0292 (10)	−0.0054 (7)	−0.0074 (7)	0.0009 (8)
N2	0.0310 (10)	0.0296 (9)	0.0341 (10)	−0.0057 (7)	−0.0078 (8)	0.0028 (8)
C1	0.0261 (10)	0.0316 (10)	0.0337 (10)	−0.0023 (8)	−0.0051 (8)	−0.0004 (8)
C2	0.0291 (11)	0.0343 (13)	0.0255 (10)	−0.0043 (9)	−0.0053 (8)	−0.0002 (9)
C3	0.0303 (11)	0.0304 (10)	0.0324 (11)	−0.0024 (8)	−0.0076 (8)	0.0015 (8)
C4	0.0318 (11)	0.0351 (12)	0.0391 (12)	−0.0035 (9)	−0.0073 (9)	0.0021 (10)
C5	0.0367 (12)	0.0328 (11)	0.0376 (12)	−0.0100 (9)	−0.0067 (9)	0.0068 (9)
C6	0.0361 (12)	0.0308 (11)	0.0412 (12)	−0.0012 (9)	−0.0070 (9)	−0.0032 (9)
C7	0.0294 (11)	0.0340 (11)	0.0346 (11)	−0.0009 (9)	−0.0054 (9)	−0.0030 (9)
C8	0.0403 (12)	0.0289 (10)	0.0306 (11)	−0.0134 (9)	−0.0062 (9)	0.0012 (9)
C9	0.0446 (13)	0.0386 (12)	0.0397 (13)	−0.0128 (10)	−0.0126 (10)	0.0054 (10)
C10	0.0624 (18)	0.0504 (15)	0.0353 (13)	−0.0259 (14)	−0.0200 (12)	0.0064 (11)
C11	0.077 (3)	0.042 (3)	0.030 (3)	−0.026 (2)	−0.005 (2)	−0.0064 (16)
C12	0.0558 (15)	0.0360 (12)	0.0462 (14)	−0.0116 (11)	−0.0015 (12)	−0.0044 (11)
C13	0.0431 (13)	0.0350 (12)	0.0341 (12)	−0.0106 (10)	−0.0081 (10)	−0.0012 (10)
Cl1'	0.087 (12)	0.059 (11)	0.037 (8)	−0.037 (8)	0.010 (7)	−0.020 (7)
N1'	0.031 (6)	0.032 (5)	0.029 (7)	−0.002 (5)	−0.005 (6)	0.000 (5)
N2'	0.030 (6)	0.034 (5)	0.034 (8)	−0.002 (5)	−0.006 (6)	−0.001 (5)
C1'	0.0261 (10)	0.0316 (10)	0.0337 (10)	−0.0023 (8)	−0.0051 (8)	−0.0004 (8)
C2'	0.034 (6)	0.031 (6)	0.030 (6)	−0.004 (5)	−0.008 (5)	0.000 (5)
C3'	0.038 (7)	0.033 (7)	0.034 (6)	−0.007 (6)	−0.012 (5)	0.003 (6)
C4'	0.044 (7)	0.040 (7)	0.036 (7)	−0.011 (6)	−0.012 (6)	−0.003 (6)
C5'	0.051 (6)	0.036 (6)	0.039 (6)	−0.015 (5)	−0.003 (5)	−0.001 (5)
C6'	0.049 (7)	0.035 (8)	0.038 (7)	−0.010 (6)	−0.004 (6)	−0.006 (6)
C7'	0.036 (6)	0.029 (6)	0.035 (6)	−0.008 (5)	−0.004 (5)	0.001 (5)
C8'	0.040 (6)	0.045 (5)	0.046 (8)	−0.008 (5)	−0.006 (6)	−0.002 (5)
C9'	0.039 (6)	0.041 (7)	0.052 (9)	−0.010 (5)	−0.003 (6)	0.004 (6)
C10'	0.045 (7)	0.043 (5)	0.069 (9)	−0.009 (5)	−0.003 (7)	0.006 (5)
C11'	0.0402 (4)	0.0351 (3)	0.0755 (5)	−0.0120 (3)	−0.0073 (3)	0.0114 (3)
C12'	0.044 (6)	0.040 (7)	0.058 (10)	−0.003 (5)	−0.006 (6)	0.002 (6)
C13'	0.050 (7)	0.049 (6)	0.067 (10)	−0.009 (5)	−0.003 (7)	−0.002 (6)

Geometric parameters (Å, º)

Cl1—C5	1.740 (2)	Cl1'—C5'	1.739 (9)
N1—N2	1.242 (3)	N1'—N2'	1.246 (10)
N1—C1	1.479 (3)	N1'—C1'	1.480 (11)
N2—C8	1.440 (3)	N2'—C8'	1.449 (9)
C1—C2	1.524 (3)	C1'—C2'	1.526 (9)
C1—C1^i	1.544 (4)	C1'—C1'^i	1.547 (10)
C1—H1	1.0000	C1'—H1'	1.0000
C2—C7	1.388 (3)	C2'—C3'	1.3900
C2—C3	1.400 (3)	C2'—C7'	1.3900
C3—C4	1.381 (3)	C3'—C4'	1.3900
C3—H3	0.9500	C3'—H3'	0.9500
C4—C5	1.397 (3)	C4'—C5'	1.3900
C4—H4	0.9500	C4'—H4'	0.9500
C5—C6	1.386 (3)	C5'—C6'	1.3900
C6—C7	1.389 (3)	C6'—C7'	1.3900
C6—H6	0.9500	C6'—H6'	0.9500
C7—H7	0.9500	C7'—H7'	0.9500
C8—C9	1.385 (3)	C8'—C9'	1.3900
C8—C13	1.396 (3)	C8'—C13'	1.3900
C9—C10	1.393 (4)	C9'—C10'	1.3900
C9—H9	0.9500	C9'—H9'	0.9500
C10—C11	1.389 (7)	C10'—C11'	1.3900
C10—H10	0.9500	C10'—H10'	0.9500
C11—C12	1.394 (6)	C11'—C12'	1.3900
C11—H11	0.9500	C11'—H11'	0.9500
C12—C13	1.379 (3)	C12'—C13'	1.3900
C12—H12	0.9500	C12'—H12'	0.9500
C13—H13	0.9500	C13'—H13'	0.9500
N2—N1—C1	111.55 (18)	N2'—N1'—C1'	111.7 (14)
N1—N2—C8	113.89 (19)	N1'—N2'—C8'	111.5 (13)
N1—C1—C2	108.00 (17)	N1'—C1'—C2'	109.1 (12)
N1—C1—C1^i	106.3 (2)	N1'—C1'—C1'^i	109.1 (18)
C2—C1—C1^i	111.6 (2)	C2'—C1'—C1'^i	124 (2)
N1—C1—H1	110.3	N1'—C1'—H1'	104.1
C2—C1—H1	110.3	C2'—C1'—H1'	104.1
C1^i—C1—H1	110.3	C1'^i—C1'—H1'	104.1
C7—C2—C3	119.3 (2)	C3'—C2'—C7'	120.0
C7—C2—C1	120.54 (19)	C3'—C2'—C1'	119.8 (10)
C3—C2—C1	120.1 (2)	C7'—C2'—C1'	120.2 (10)
C4—C3—C2	120.7 (2)	C4'—C3'—C2'	120.0
C4—C3—H3	119.7	C4'—C3'—H3'	120.0
C2—C3—H3	119.7	C2'—C3'—H3'	120.0
C3—C4—C5	119.0 (2)	C3'—C4'—C5'	120.0
C3—C4—H4	120.5	C3'—C4'—H4'	120.0
C5—C4—H4	120.5	C5'—C4'—H4'	120.0
C6—C5—C4	121.2 (2)	C4'—C5'—C6'	120.0
C6—C5—Cl1	119.23 (17)	C4'—C5'—Cl1'	119.3 (10)
C4—C5—Cl1	119.62 (18)	C6'—C5'—Cl1'	120.7 (10)
C5—C6—C7	119.1 (2)	C7'—C6'—C5'	120.0
C5—C6—H6	120.5	C7'—C6'—H6'	120.0
C7—C6—H6	120.5	C5'—C6'—H6'	120.0
C2—C7—C6	120.8 (2)	C6'—C7'—C2'	120.0
C2—C7—H7	119.6	C6'—C7'—H7'	120.0
C6—C7—H7	119.6	C2'—C7'—H7'	120.0
C9—C8—C13	120.5 (2)	C9'—C8'—C13'	120.0
C9—C8—N2	115.1 (2)	C9'—C8'—N2'	112.3 (10)
C13—C8—N2	124.4 (2)	C13'—C8'—N2'	127.7 (10)
C8—C9—C10	119.7 (2)	C8'—C9'—C10'	120.0
C8—C9—H9	120.2	C8'—C9'—H9'	120.0
C10—C9—H9	120.2	C10'—C9'—H9'	120.0
C11—C10—C9	120.5 (3)	C11'—C10'—C9'	120.0
C11—C10—H10	119.8	C11'—C10'—H10'	120.0
C9—C10—H10	119.8	C9'—C10'—H10'	120.0
C10—C11—C12	118.9 (4)	C10'—C11'—C12'	120.0
C10—C11—H11	120.5	C10'—C11'—H11'	120.0
C12—C11—H11	120.5	C12'—C11'—H11'	120.0
C13—C12—C11	121.3 (3)	C13'—C12'—C11'	120.0
C13—C12—H12	119.4	C13'—C12'—H12'	120.0
C11—C12—H12	119.4	C11'—C12'—H12'	120.0
C12—C13—C8	119.2 (2)	C12'—C13'—C8'	120.0
C12—C13—H13	120.4	C12'—C13'—H13'	120.0
C8—C13—H13	120.4	C8'—C13'—H13'	120.0
C1—N1—N2—C8	179.32 (17)	C1'—N1'—N2'—C8'	179.98 (18)
N2—N1—C1—C2	−110.4 (2)	N2'—N1'—C1'—C2'	126.1 (15)
N2—N1—C1—C1^i	129.7 (2)	N2'—N1'—C1'—C1'^i	−95 (3)
N1—C1—C2—C7	127.5 (2)	N1'—C1'—C2'—C3'	−112.1 (16)
C1^i—C1—C2—C7	−116.0 (3)	C1'^i—C1'—C2'—C3'	117 (3)
N1—C1—C2—C3	−49.7 (3)	N1'—C1'—C2'—C7'	68 (2)
C1^i—C1—C2—C3	66.7 (3)	C1'^i—C1'—C2'—C7'	−63 (3)
C7—C2—C3—C4	−0.1 (3)	C7'—C2'—C3'—C4'	0.0
C1—C2—C3—C4	177.2 (2)	C1'—C2'—C3'—C4'	180 (2)
C2—C3—C4—C5	1.0 (4)	C2'—C3'—C4'—C5'	0.0
C3—C4—C5—C6	−1.0 (4)	C3'—C4'—C5'—C6'	0.0
C3—C4—C5—Cl1	179.05 (18)	C3'—C4'—C5'—Cl1'	180 (3)
C4—C5—C6—C7	0.1 (4)	C4'—C5'—C6'—C7'	0.0
Cl1—C5—C6—C7	−179.99 (18)	Cl1'—C5'—C6'—C7'	−180 (3)
C3—C2—C7—C6	−0.8 (3)	C5'—C6'—C7'—C2'	0.0
C1—C2—C7—C6	−178.1 (2)	C3'—C2'—C7'—C6'	0.0
C5—C6—C7—C2	0.9 (4)	C1'—C2'—C7'—C6'	−180 (2)
N1—N2—C8—C9	−176.14 (18)	N1'—N2'—C8'—C9'	0.0 (2)
N1—N2—C8—C13	4.7 (3)	N1'—N2'—C8'—C13'	180.0 (2)
C13—C8—C9—C10	0.0 (3)	C13'—C8'—C9'—C10'	0.0
N2—C8—C9—C10	−179.19 (19)	N2'—C8'—C9'—C10'	180.0 (3)
C8—C9—C10—C11	0.2 (7)	C8'—C9'—C10'—C11'	0.0
C9—C10—C11—C12	0.0 (12)	C9'—C10'—C11'—C12'	0.0
C10—C11—C12—C13	−0.5 (12)	C10'—C11'—C12'—C13'	0.0
C11—C12—C13—C8	0.8 (7)	C11'—C12'—C13'—C8'	0.0
C9—C8—C13—C12	−0.5 (3)	C9'—C8'—C13'—C12'	0.0
N2—C8—C13—C12	178.6 (2)	N2'—C8'—C13'—C12'	−180.0 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

1,1'-[1,2-Bis(4-chlorophenyl)ethane-1,2-diyl]bis(phenyldiazene) (IIc)

Crystal data

C26H20Cl2N4	F(000) = 952
Mr = 459.36	Dx = 1.317 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 22.657 (10) Å	Cell parameters from 3065 reflections
b = 5.4399 (18) Å	θ = 2.2–30.3°
c = 19.086 (6) Å	µ = 0.30 mm^−1
β = 99.967 (7)°	T = 100 K
V = 2316.9 (15) Å^3	Needle, yellow
Z = 4	0.50 × 0.06 × 0.05 mm

Data collection

Rigaku AFC12 diffractometer	3042 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm^-1	Rint = 0.027
profile data from ω–scans	θmax = 30.3°, θmin = 2.6°
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012)	h = −29→23
Tmin = 0.797, Tmax = 0.985	k = −7→7
8691 measured reflections	l = −26→26
4406 independent reflections

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)] = 0.047	w = 1/[σ^2(Fo^2) + (0.0544P)^2 + 0.3437P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.123	(Δ/σ)max = 0.007
S = 1.08	Δρmax = 0.18 e Å^−3
4406 reflections	Δρmin = −0.18 e Å^−3
724 parameters	Absolute structure: Flack x determined using 681 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
4197 restraints	Absolute structure parameter: 0.54 (14)

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	Occ. (<1)
C1A	0.5104 (5)	0.638 (3)	0.4663 (6)	0.0324 (17)	0.393 (3)
H1A	0.520796	0.475561	0.489848	0.039*	0.393 (3)
C2A	0.5415 (4)	0.6636 (19)	0.4025 (4)	0.0302 (18)	0.393 (3)
C3A	0.5799 (4)	0.4777 (18)	0.3884 (5)	0.0339 (19)	0.393 (3)
H3A	0.587019	0.339808	0.419292	0.041*	0.393 (3)
C4A	0.6079 (5)	0.4936 (18)	0.3293 (5)	0.037 (2)	0.393 (3)
H4A	0.634105	0.366532	0.319684	0.044*	0.393 (3)
C5A	0.5974 (4)	0.6953 (19)	0.2841 (5)	0.0344 (17)	0.393 (3)
C6A	0.5590 (4)	0.8812 (17)	0.2982 (5)	0.032 (2)	0.393 (3)
H6A	0.551882	1.019102	0.267323	0.039*	0.393 (3)
C7A	0.5310 (4)	0.8653 (17)	0.3573 (5)	0.0336 (17)	0.393 (3)
H7A	0.504795	0.992383	0.366930	0.040*	0.393 (3)
Cl1A	0.6330 (3)	0.7236 (18)	0.2126 (4)	0.0545 (15)	0.393 (3)
N1A	0.4459 (5)	0.654 (3)	0.4427 (7)	0.0328 (18)	0.393 (3)
N2A	0.4108 (5)	0.487 (3)	0.4646 (8)	0.0343 (19)	0.393 (3)
C8A	0.3477 (3)	0.488 (2)	0.4335 (5)	0.0358 (16)	0.393 (3)
C9A	0.3204 (4)	0.6578 (17)	0.3839 (5)	0.043 (2)	0.393 (3)
H9A	0.343876	0.778782	0.365642	0.051*	0.393 (3)
C10A	0.2587 (4)	0.6511 (18)	0.3611 (4)	0.044 (2)	0.393 (3)
H10A	0.240073	0.767491	0.327241	0.053*	0.393 (3)
C11A	0.2243 (3)	0.474 (2)	0.3878 (5)	0.048 (3)	0.393 (3)
H11A	0.182186	0.469521	0.372251	0.058*	0.393 (3)
C12A	0.2516 (4)	0.3038 (16)	0.4374 (5)	0.0405 (19)	0.393 (3)
H12A	0.228103	0.182837	0.455663	0.049*	0.393 (3)
C13A	0.3133 (4)	0.3105 (17)	0.4602 (5)	0.0368 (19)	0.393 (3)
H13A	0.331906	0.194123	0.494065	0.044*	0.393 (3)
C1B	0.5287 (5)	0.847 (2)	0.5200 (6)	0.0313 (16)	0.393 (3)
H1B	0.508502	1.000065	0.499019	0.038*	0.393 (3)
C2B	0.5942 (3)	0.9071 (16)	0.5433 (4)	0.0290 (17)	0.393 (3)
C3B	0.6194 (3)	1.1188 (15)	0.5202 (5)	0.0369 (18)	0.393 (3)
H3B	0.595309	1.229516	0.489072	0.044*	0.393 (3)
C4B	0.6799 (4)	1.1685 (14)	0.5428 (5)	0.041 (2)	0.393 (3)
H4B	0.697133	1.313140	0.527028	0.049*	0.393 (3)
C5B	0.7152 (3)	1.0065 (17)	0.5884 (5)	0.0416 (16)	0.393 (3)
C6B	0.6900 (3)	0.7948 (16)	0.6114 (5)	0.042 (2)	0.393 (3)
H6B	0.714127	0.684053	0.642546	0.050*	0.393 (3)
C7B	0.6295 (3)	0.7451 (14)	0.5888 (5)	0.0365 (17)	0.393 (3)
H7B	0.612303	0.600426	0.604591	0.044*	0.393 (3)
Cl1B	0.79063 (17)	1.0735 (10)	0.6158 (2)	0.0544 (11)	0.393 (3)
N1B	0.5028 (5)	0.787 (2)	0.5857 (6)	0.0338 (15)	0.393 (3)
N2B	0.4637 (5)	0.919 (2)	0.5967 (6)	0.0347 (17)	0.393 (3)
C8B	0.4396 (4)	0.8659 (16)	0.6592 (4)	0.0345 (15)	0.393 (3)
C9B	0.4534 (4)	0.6535 (16)	0.6991 (5)	0.039 (2)	0.393 (3)
H9B	0.479865	0.535299	0.684967	0.047*	0.393 (3)
C10B	0.4285 (4)	0.6141 (16)	0.7598 (5)	0.0414 (19)	0.393 (3)
H10B	0.437929	0.468904	0.787118	0.050*	0.393 (3)
C11B	0.3897 (4)	0.7870 (19)	0.7805 (4)	0.037 (3)	0.393 (3)
H11B	0.372711	0.760057	0.821994	0.045*	0.393 (3)
C12B	0.3759 (4)	0.9994 (16)	0.7406 (5)	0.0428 (19)	0.393 (3)
H12B	0.349429	1.117607	0.754721	0.051*	0.393 (3)
C13B	0.4008 (4)	1.0388 (14)	0.6799 (4)	0.0365 (19)	0.393 (3)
H13B	0.391365	1.184006	0.652570	0.044*	0.393 (3)
C1C	0.4841 (5)	0.643 (3)	0.4808 (7)	0.0317 (17)	0.378 (3)
H1C	0.503532	0.488767	0.502142	0.038*	0.378 (3)
C2C	0.4166 (3)	0.6085 (17)	0.4611 (5)	0.0340 (18)	0.378 (3)
C3C	0.3932 (3)	0.3877 (16)	0.4806 (5)	0.0368 (18)	0.378 (3)
H3C	0.418360	0.274155	0.509585	0.044*	0.378 (3)
C4C	0.3331 (4)	0.3329 (14)	0.4577 (5)	0.039 (2)	0.378 (3)
H4C	0.317057	0.182011	0.471074	0.047*	0.378 (3)
C5C	0.2963 (3)	0.4990 (17)	0.4153 (5)	0.0416 (16)	0.378 (3)
C6C	0.3197 (3)	0.7199 (16)	0.3958 (5)	0.038 (2)	0.378 (3)
H6C	0.294585	0.833383	0.366776	0.045*	0.378 (3)
C7C	0.3799 (4)	0.7746 (14)	0.4186 (5)	0.0379 (18)	0.378 (3)
H7C	0.395888	0.925533	0.405287	0.045*	0.378 (3)
Cl1C	0.22228 (18)	0.4296 (11)	0.3835 (3)	0.0659 (15)	0.378 (3)
N1C	0.5086 (5)	0.714 (2)	0.4177 (6)	0.0342 (16)	0.378 (3)
N2C	0.5496 (5)	0.570 (2)	0.4052 (6)	0.0312 (16)	0.378 (3)
C8C	0.5754 (4)	0.6381 (17)	0.3435 (4)	0.0348 (15)	0.378 (3)
C9C	0.5608 (4)	0.8392 (16)	0.2989 (5)	0.034 (2)	0.378 (3)
H9C	0.530698	0.951206	0.307611	0.041*	0.378 (3)
C10C	0.5902 (4)	0.8764 (17)	0.2416 (5)	0.0374 (19)	0.378 (3)
H10C	0.580165	1.013818	0.211155	0.045*	0.378 (3)
C11C	0.6342 (4)	0.713 (2)	0.2289 (5)	0.040 (3)	0.378 (3)
H11C	0.654257	0.737933	0.189717	0.048*	0.378 (3)
C12C	0.6488 (4)	0.5114 (18)	0.2734 (5)	0.046 (2)	0.378 (3)
H12C	0.678882	0.399435	0.264736	0.055*	0.378 (3)
C13C	0.6194 (4)	0.4742 (16)	0.3307 (4)	0.0364 (19)	0.378 (3)
H13C	0.629415	0.336820	0.361193	0.044*	0.378 (3)
C1D	0.4988 (5)	0.861 (3)	0.5328 (7)	0.0337 (17)	0.378 (3)
H1D	0.487714	1.019595	0.507386	0.040*	0.378 (3)
C2D	0.4714 (5)	0.848 (2)	0.5988 (5)	0.034 (2)	0.378 (3)
C3D	0.4317 (5)	1.0231 (19)	0.6165 (5)	0.0347 (19)	0.378 (3)
H3D	0.422418	1.164706	0.587585	0.042*	0.378 (3)
C4D	0.4056 (5)	0.9907 (19)	0.6767 (6)	0.038 (2)	0.378 (3)
H4D	0.378515	1.110155	0.688813	0.046*	0.378 (3)
C5D	0.4192 (6)	0.784 (2)	0.7190 (5)	0.0381 (18)	0.378 (3)
C6D	0.4589 (7)	0.609 (2)	0.7013 (6)	0.035 (2)	0.378 (3)
H6D	0.468181	0.467261	0.730206	0.042*	0.378 (3)
C7D	0.4850 (6)	0.641 (2)	0.6411 (6)	0.0357 (19)	0.378 (3)
H7D	0.512084	0.521807	0.628977	0.043*	0.378 (3)
Cl1D	0.3832 (3)	0.7635 (15)	0.7917 (4)	0.0476 (13)	0.378 (3)
N1D	0.5657 (5)	0.852 (3)	0.5591 (9)	0.0318 (18)	0.378 (3)
N2D	0.5926 (4)	1.028 (3)	0.5419 (8)	0.0343 (19)	0.378 (3)
C8D	0.6558 (3)	1.015 (2)	0.5662 (6)	0.0376 (16)	0.378 (3)
C9D	0.6839 (4)	0.8151 (17)	0.6034 (5)	0.044 (2)	0.378 (3)
H9D	0.661053	0.675557	0.612263	0.052*	0.378 (3)
C10D	0.7454 (4)	0.8194 (19)	0.6276 (5)	0.046 (2)	0.378 (3)
H10D	0.764565	0.682947	0.653025	0.055*	0.378 (3)
C11D	0.7788 (3)	1.024 (2)	0.6147 (7)	0.055 (3)	0.378 (3)
H11D	0.820821	1.026549	0.631204	0.066*	0.378 (3)
C12D	0.7507 (4)	1.2233 (19)	0.5775 (7)	0.049 (2)	0.378 (3)
H12D	0.773566	1.362763	0.568619	0.058*	0.378 (3)
C13D	0.6892 (4)	1.2189 (18)	0.5533 (6)	0.042 (2)	0.378 (3)
H13D	0.670054	1.355378	0.527856	0.051*	0.378 (3)
C1E	0.5147 (8)	0.856 (5)	0.5361 (11)	0.035 (2)	0.229 (2)
H1E	0.502937	1.019244	0.513677	0.042*	0.229 (2)
C2E	0.4815 (8)	0.815 (4)	0.5991 (8)	0.036 (2)	0.229 (2)
C3E	0.4415 (9)	1.007 (3)	0.6028 (8)	0.038 (2)	0.229 (2)
H3E	0.435937	1.130370	0.567124	0.046*	0.229 (2)
C4E	0.4095 (8)	1.017 (3)	0.6587 (8)	0.036 (2)	0.229 (2)
H4E	0.382131	1.147773	0.661184	0.043*	0.229 (2)
C5E	0.4176 (9)	0.836 (3)	0.7109 (8)	0.038 (2)	0.229 (2)
C6E	0.4576 (11)	0.645 (3)	0.7072 (10)	0.036 (2)	0.229 (2)
H6E	0.463116	0.521220	0.742921	0.043*	0.229 (2)
C7E	0.4896 (10)	0.635 (4)	0.6514 (10)	0.038 (2)	0.229 (2)
H7E	0.516923	0.503812	0.648861	0.045*	0.229 (2)
Cl1E	0.3737 (7)	0.815 (3)	0.7772 (8)	0.081 (4)	0.229 (2)
N1E	0.5794 (8)	0.846 (5)	0.5567 (15)	0.035 (2)	0.229 (2)
N2E	0.6081 (7)	1.041 (4)	0.5411 (14)	0.034 (2)	0.229 (2)
C8E	0.6714 (5)	1.020 (3)	0.5674 (9)	0.038 (2)	0.229 (2)
C9E	0.6930 (6)	0.862 (3)	0.6232 (9)	0.043 (3)	0.229 (2)
H9E	0.667425	0.740291	0.637567	0.052*	0.229 (2)
C10E	0.7520 (7)	0.882 (3)	0.6580 (7)	0.050 (3)	0.229 (2)
H10E	0.766729	0.773620	0.696189	0.060*	0.229 (2)
C11E	0.7894 (5)	1.059 (3)	0.6370 (8)	0.052 (3)	0.229 (2)
H11E	0.829736	1.072742	0.660803	0.062*	0.229 (2)
C12E	0.7679 (6)	1.217 (3)	0.5812 (9)	0.046 (3)	0.229 (2)
H12E	0.793439	1.338538	0.566793	0.056*	0.229 (2)
C13E	0.7089 (6)	1.197 (3)	0.5463 (8)	0.043 (3)	0.229 (2)
H13E	0.694135	1.305212	0.508169	0.052*	0.229 (2)
C1F	0.5004 (8)	0.655 (5)	0.4807 (10)	0.034 (2)	0.229 (2)
H1F	0.509473	0.491900	0.504572	0.040*	0.229 (2)
C2F	0.5292 (7)	0.663 (3)	0.4156 (7)	0.032 (2)	0.229 (2)
C3F	0.5679 (8)	0.482 (3)	0.3994 (8)	0.036 (2)	0.229 (2)
H3F	0.575361	0.339831	0.428647	0.043*	0.229 (2)
C4F	0.5957 (7)	0.508 (3)	0.3404 (9)	0.036 (2)	0.229 (2)
H4F	0.622147	0.383695	0.329252	0.043*	0.229 (2)
C5F	0.5848 (7)	0.715 (3)	0.2976 (7)	0.036 (2)	0.229 (2)
C6F	0.5461 (7)	0.897 (3)	0.3138 (7)	0.034 (2)	0.229 (2)
H6F	0.538691	1.038324	0.284537	0.041*	0.229 (2)
C7F	0.5183 (6)	0.870 (3)	0.3728 (7)	0.035 (2)	0.229 (2)
H7F	0.491903	0.994465	0.383932	0.042*	0.229 (2)
Cl1F	0.6182 (6)	0.742 (3)	0.2222 (8)	0.061 (3)	0.229 (2)
N1F	0.4344 (8)	0.669 (4)	0.4531 (13)	0.035 (2)	0.229 (2)
N2F	0.4192 (7)	0.455 (4)	0.4572 (14)	0.035 (2)	0.229 (2)
C8F	0.3558 (5)	0.473 (3)	0.4388 (9)	0.037 (2)	0.229 (2)
C9F	0.3257 (7)	0.684 (3)	0.4114 (8)	0.040 (2)	0.229 (2)
H9F	0.347497	0.830299	0.406631	0.047*	0.229 (2)
C10F	0.2638 (7)	0.681 (3)	0.3910 (8)	0.045 (3)	0.229 (2)
H10F	0.243225	0.824910	0.372318	0.054*	0.229 (2)
C11F	0.2319 (5)	0.466 (3)	0.3980 (9)	0.050 (3)	0.229 (2)
H11F	0.189541	0.464187	0.384117	0.060*	0.229 (2)
C12F	0.2619 (7)	0.255 (3)	0.4254 (9)	0.044 (3)	0.229 (2)
H12F	0.240129	0.108850	0.430228	0.052*	0.229 (2)
C13F	0.3239 (7)	0.258 (3)	0.4458 (9)	0.040 (2)	0.229 (2)
H13F	0.344401	0.114235	0.464542	0.048*	0.229 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.035 (3)	0.027 (3)	0.033 (3)	0.002 (3)	0.001 (3)	0.002 (3)
C2A	0.028 (3)	0.033 (3)	0.028 (3)	−0.003 (3)	0.000 (3)	−0.002 (3)
C3A	0.036 (4)	0.030 (3)	0.034 (3)	0.003 (3)	0.003 (3)	0.000 (3)
C4A	0.039 (4)	0.035 (4)	0.038 (4)	0.001 (3)	0.009 (3)	0.000 (3)
C5A	0.035 (3)	0.034 (3)	0.034 (3)	−0.005 (3)	0.006 (3)	−0.007 (3)
C6A	0.037 (4)	0.028 (4)	0.031 (4)	−0.005 (3)	0.003 (3)	−0.003 (3)
C7A	0.033 (3)	0.033 (3)	0.034 (3)	0.002 (3)	0.005 (3)	0.001 (3)
Cl1A	0.058 (3)	0.066 (3)	0.046 (3)	−0.009 (2)	0.027 (2)	−0.005 (2)
N1A	0.034 (3)	0.032 (3)	0.034 (3)	−0.001 (3)	0.007 (3)	0.000 (3)
N2A	0.041 (3)	0.031 (4)	0.032 (3)	0.001 (3)	0.007 (3)	−0.001 (3)
C8A	0.034 (3)	0.040 (3)	0.034 (3)	0.002 (3)	0.008 (2)	−0.002 (3)
C9A	0.043 (3)	0.044 (4)	0.041 (4)	0.008 (3)	0.006 (3)	0.000 (4)
C10A	0.044 (3)	0.053 (4)	0.037 (4)	0.012 (3)	0.008 (3)	−0.003 (4)
C11A	0.043 (4)	0.055 (4)	0.045 (5)	0.011 (4)	0.003 (4)	−0.006 (4)
C12A	0.039 (3)	0.043 (4)	0.040 (4)	0.000 (3)	0.010 (3)	−0.004 (3)
C13A	0.036 (3)	0.037 (4)	0.040 (4)	0.006 (3)	0.012 (3)	−0.005 (3)
C1B	0.033 (3)	0.031 (3)	0.030 (3)	0.000 (3)	0.005 (3)	0.004 (3)
C2B	0.030 (3)	0.031 (3)	0.026 (3)	0.002 (3)	0.005 (3)	0.000 (3)
C3B	0.039 (3)	0.037 (4)	0.035 (4)	−0.003 (3)	0.005 (3)	0.002 (3)
C4B	0.037 (3)	0.043 (4)	0.041 (4)	−0.008 (3)	0.005 (3)	−0.003 (3)
C5B	0.037 (3)	0.044 (3)	0.041 (3)	−0.004 (3)	0.000 (3)	−0.012 (3)
C6B	0.041 (3)	0.042 (4)	0.038 (4)	0.003 (3)	−0.003 (3)	−0.005 (3)
C7B	0.041 (3)	0.028 (3)	0.037 (3)	0.003 (3)	−0.006 (3)	0.000 (3)
Cl1B	0.0365 (16)	0.069 (3)	0.056 (2)	−0.0094 (17)	0.0051 (15)	−0.014 (2)
N1B	0.036 (3)	0.036 (3)	0.030 (3)	−0.004 (3)	0.006 (2)	0.002 (3)
N2B	0.035 (3)	0.035 (3)	0.031 (3)	−0.002 (3)	0.000 (3)	0.002 (3)
C8B	0.035 (3)	0.035 (3)	0.030 (3)	−0.010 (2)	−0.002 (2)	−0.002 (3)
C9B	0.043 (4)	0.034 (4)	0.037 (4)	−0.006 (3)	−0.002 (3)	0.000 (3)
C10B	0.047 (4)	0.039 (4)	0.034 (3)	−0.008 (3)	−0.004 (3)	0.004 (3)
C11B	0.043 (5)	0.032 (5)	0.034 (5)	−0.015 (4)	−0.001 (4)	0.001 (4)
C12B	0.048 (4)	0.036 (4)	0.044 (4)	−0.008 (3)	0.005 (3)	−0.003 (3)
C13B	0.046 (3)	0.027 (3)	0.035 (4)	−0.005 (3)	0.004 (3)	0.000 (3)
C1C	0.033 (3)	0.030 (3)	0.032 (3)	−0.001 (3)	0.007 (3)	0.004 (3)
C2C	0.035 (3)	0.036 (4)	0.033 (3)	0.000 (3)	0.008 (3)	0.002 (3)
C3C	0.041 (3)	0.036 (4)	0.034 (3)	0.003 (3)	0.008 (3)	−0.002 (3)
C4C	0.039 (3)	0.039 (4)	0.041 (4)	−0.001 (3)	0.009 (3)	−0.004 (3)
C5C	0.039 (3)	0.044 (3)	0.041 (3)	0.002 (3)	0.006 (3)	−0.008 (3)
C6C	0.036 (3)	0.039 (4)	0.037 (4)	0.009 (3)	0.005 (3)	−0.001 (3)
C7C	0.038 (3)	0.032 (3)	0.042 (3)	0.000 (3)	0.001 (3)	0.003 (3)
Cl1C	0.0363 (19)	0.074 (3)	0.080 (3)	−0.0077 (19)	−0.0090 (19)	−0.030 (3)
N1C	0.035 (3)	0.034 (3)	0.034 (3)	−0.001 (3)	0.004 (3)	0.001 (3)
N2C	0.029 (3)	0.032 (3)	0.032 (3)	−0.002 (3)	0.002 (2)	0.001 (3)
C8C	0.035 (3)	0.038 (3)	0.032 (3)	−0.006 (3)	0.006 (2)	−0.005 (3)
C9C	0.039 (4)	0.032 (4)	0.031 (3)	−0.006 (3)	0.003 (3)	−0.007 (3)
C10C	0.045 (4)	0.034 (4)	0.034 (4)	−0.010 (3)	0.010 (3)	0.002 (3)
C11C	0.044 (5)	0.040 (5)	0.037 (5)	−0.004 (4)	0.010 (4)	−0.006 (4)
C12C	0.052 (4)	0.043 (4)	0.044 (4)	−0.003 (3)	0.014 (3)	−0.007 (3)
C13C	0.041 (4)	0.033 (4)	0.036 (3)	−0.003 (3)	0.009 (3)	−0.003 (3)
C1D	0.034 (3)	0.029 (3)	0.034 (3)	0.002 (3)	−0.005 (3)	0.004 (3)
C2D	0.035 (4)	0.033 (4)	0.031 (3)	0.001 (3)	−0.004 (3)	0.004 (3)
C3D	0.042 (4)	0.027 (3)	0.033 (4)	0.000 (3)	−0.001 (3)	0.004 (3)
C4D	0.046 (4)	0.034 (4)	0.034 (4)	−0.004 (3)	0.004 (3)	0.001 (3)
C5D	0.044 (3)	0.035 (4)	0.032 (3)	−0.010 (3)	−0.003 (3)	−0.003 (3)
C6D	0.040 (4)	0.029 (4)	0.032 (4)	−0.001 (3)	−0.007 (3)	0.004 (3)
C7D	0.039 (4)	0.031 (3)	0.033 (4)	0.004 (3)	−0.006 (3)	0.004 (3)
Cl1D	0.054 (3)	0.048 (2)	0.041 (3)	0.0001 (18)	0.008 (2)	0.007 (2)
N1D	0.033 (3)	0.029 (3)	0.032 (3)	−0.001 (3)	0.001 (3)	0.004 (3)
N2D	0.037 (3)	0.035 (3)	0.031 (3)	−0.005 (3)	0.003 (3)	−0.001 (3)
C8D	0.038 (3)	0.041 (3)	0.033 (3)	−0.006 (3)	0.005 (3)	−0.002 (3)
C9D	0.045 (4)	0.045 (4)	0.038 (4)	−0.003 (3)	0.000 (3)	−0.002 (4)
C10D	0.045 (4)	0.050 (4)	0.039 (4)	0.000 (3)	0.001 (3)	−0.007 (4)
C11D	0.048 (5)	0.057 (5)	0.057 (5)	−0.002 (4)	−0.004 (4)	−0.011 (4)
C12D	0.042 (4)	0.053 (4)	0.048 (4)	−0.014 (3)	0.000 (4)	−0.005 (4)
C13D	0.038 (4)	0.047 (4)	0.041 (4)	−0.010 (3)	0.005 (3)	−0.005 (3)
C1E	0.038 (3)	0.032 (3)	0.033 (3)	0.000 (3)	0.000 (3)	0.002 (3)
C2E	0.038 (4)	0.034 (4)	0.033 (3)	0.001 (3)	−0.001 (3)	0.000 (3)
C3E	0.040 (4)	0.034 (4)	0.037 (4)	0.000 (4)	−0.001 (4)	0.002 (4)
C4E	0.042 (4)	0.031 (4)	0.031 (4)	−0.005 (4)	0.001 (4)	0.001 (4)
C5E	0.045 (4)	0.035 (4)	0.030 (4)	−0.007 (3)	0.000 (3)	−0.002 (3)
C6E	0.040 (4)	0.033 (4)	0.030 (4)	−0.004 (4)	−0.005 (4)	0.001 (4)
C7E	0.040 (4)	0.034 (4)	0.034 (4)	0.001 (4)	−0.003 (3)	0.003 (3)
Cl1E	0.091 (7)	0.094 (8)	0.053 (5)	−0.013 (5)	−0.001 (5)	−0.007 (5)
N1E	0.037 (4)	0.031 (4)	0.033 (4)	0.000 (3)	0.001 (3)	0.002 (3)
N2E	0.037 (4)	0.032 (4)	0.033 (4)	0.000 (4)	0.003 (4)	0.001 (4)
C8E	0.036 (3)	0.040 (3)	0.037 (3)	0.000 (3)	0.001 (3)	−0.003 (3)
C9E	0.044 (4)	0.044 (4)	0.040 (4)	0.002 (4)	−0.001 (4)	−0.003 (4)
C10E	0.048 (4)	0.050 (5)	0.049 (5)	0.007 (4)	−0.003 (4)	−0.007 (4)
C11E	0.043 (5)	0.051 (5)	0.056 (5)	0.005 (4)	−0.007 (4)	−0.007 (4)
C12E	0.037 (5)	0.048 (5)	0.052 (5)	−0.002 (4)	0.001 (4)	−0.002 (4)
C13E	0.039 (4)	0.045 (4)	0.044 (4)	0.000 (4)	0.003 (4)	−0.001 (4)
C1F	0.035 (4)	0.032 (4)	0.032 (4)	0.002 (3)	0.002 (3)	0.002 (3)
C2F	0.033 (4)	0.031 (4)	0.031 (3)	−0.001 (3)	0.002 (3)	−0.002 (3)
C3F	0.035 (4)	0.034 (4)	0.038 (4)	−0.001 (4)	0.003 (3)	0.000 (4)
C4F	0.037 (4)	0.033 (4)	0.036 (4)	0.000 (4)	0.007 (4)	−0.001 (4)
C5F	0.040 (4)	0.036 (4)	0.032 (3)	−0.005 (3)	0.007 (3)	−0.003 (3)
C6F	0.035 (4)	0.031 (4)	0.034 (4)	−0.004 (4)	0.002 (4)	−0.001 (4)
C7F	0.037 (4)	0.036 (4)	0.031 (4)	−0.004 (4)	0.002 (3)	−0.001 (3)
Cl1F	0.064 (6)	0.076 (5)	0.045 (4)	−0.009 (5)	0.017 (4)	−0.006 (4)
N1F	0.038 (4)	0.032 (4)	0.035 (4)	0.001 (3)	0.004 (3)	−0.001 (3)
N2F	0.038 (4)	0.034 (4)	0.032 (4)	0.001 (3)	0.006 (4)	0.000 (4)
C8F	0.039 (3)	0.039 (3)	0.034 (4)	0.000 (3)	0.008 (3)	−0.001 (3)
C9F	0.039 (4)	0.042 (4)	0.038 (4)	0.003 (3)	0.010 (4)	0.002 (4)
C10F	0.041 (4)	0.049 (4)	0.046 (5)	0.008 (4)	0.006 (4)	−0.001 (4)
C11F	0.046 (5)	0.054 (5)	0.049 (5)	0.002 (4)	0.007 (4)	−0.006 (4)
C12F	0.043 (4)	0.047 (4)	0.042 (5)	−0.003 (4)	0.009 (4)	−0.007 (4)
C13F	0.041 (4)	0.043 (4)	0.037 (4)	−0.003 (4)	0.009 (4)	−0.003 (4)

Geometric parameters (Å, º)

C1A—N1A	1.455 (14)	C1D—C2D	1.498 (13)
C1A—C2A	1.515 (11)	C1D—N1D	1.512 (14)
C1A—C1B	1.540 (12)	C1D—H1D	1.0000
C1A—H1A	1.0000	C2D—C3D	1.3900
C2A—C3A	1.3900	C2D—C7D	1.3900
C2A—C7A	1.3900	C3D—C4D	1.3900
C3A—C4A	1.3900	C3D—H3D	0.9500
C3A—H3A	0.9500	C4D—C5D	1.3900
C4A—C5A	1.3900	C4D—H4D	0.9500
C4A—H4A	0.9500	C5D—C6D	1.3900
C5A—C6A	1.3900	C5D—Cl1D	1.730 (9)
C5A—Cl1A	1.709 (8)	C6D—C7D	1.3900
C6A—C7A	1.3900	C6D—H6D	0.9500
C6A—H6A	0.9500	C7D—H7D	0.9500
C7A—H7A	0.9500	N1D—N2D	1.209 (15)
N1A—N2A	1.320 (16)	N2D—C8D	1.428 (11)
N2A—C8A	1.452 (12)	C8D—C9D	1.3900
C8A—C9A	1.3900	C8D—C13D	1.3900
C8A—C13A	1.3900	C9D—C10D	1.3900
C9A—C10A	1.3900	C9D—H9D	0.9500
C9A—H9A	0.9500	C10D—C11D	1.3900
C10A—C11A	1.3900	C10D—H10D	0.9500
C10A—H10A	0.9500	C11D—C12D	1.3900
C11A—C12A	1.3900	C11D—H11D	0.9500
C11A—H11A	0.9500	C12D—C13D	1.3900
C12A—C13A	1.3900	C12D—H12D	0.9500
C12A—H12A	0.9500	C13D—H13D	0.9500
C13A—H13A	0.9500	C1E—N1E	1.450 (19)
C1B—N1B	1.510 (12)	C1E—C1F	1.521 (16)
C1B—C2B	1.509 (11)	C1E—C2E	1.542 (17)
C1B—H1B	1.0000	C1E—H1E	1.0000
C2B—C3B	1.3900	C2E—C3E	1.3900
C2B—C7B	1.3900	C2E—C7E	1.3900
C3B—C4B	1.3900	C3E—C4E	1.3900
C3B—H3B	0.9500	C3E—H3E	0.9500
C4B—C5B	1.3900	C4E—C5E	1.3900
C4B—H4B	0.9500	C4E—H4E	0.9500
C5B—C6B	1.3900	C5E—C6E	1.3900
C5B—Cl1B	1.737 (7)	C5E—Cl1E	1.743 (15)
C6B—C7B	1.3900	C6E—C7E	1.3900
C6B—H6B	0.9500	C6E—H6E	0.9500
C7B—H7B	0.9500	C7E—H7E	0.9500
N1B—N2B	1.189 (14)	N1E—N2E	1.30 (2)
N2B—C8B	1.425 (10)	N2E—C8E	1.440 (15)
C8B—C9B	1.3900	C8E—C9E	1.3900
C8B—C13B	1.3900	C8E—C13E	1.3900
C9B—C10B	1.3900	C9E—C10E	1.3900
C9B—H9B	0.9500	C9E—H9E	0.9500
C10B—C11B	1.3900	C10E—C11E	1.3900
C10B—H10B	0.9500	C10E—H10E	0.9500
C11B—C12B	1.3900	C11E—C12E	1.3900
C11B—H11B	0.9500	C11E—H11E	0.9500
C12B—C13B	1.3900	C12E—C13E	1.3900
C12B—H12B	0.9500	C12E—H12E	0.9500
C13B—H13B	0.9500	C13E—H13E	0.9500
C1C—N1C	1.462 (14)	C1F—N1F	1.50 (2)
C1C—C2C	1.520 (12)	C1F—C2F	1.501 (17)
C1C—C1D	1.547 (12)	C1F—H1F	1.0000
C1C—H1C	1.0000	C2F—C3F	1.3900
C2C—C3C	1.3900	C2F—C7F	1.3900
C2C—C7C	1.3900	C3F—C4F	1.3900
C3C—C4C	1.3900	C3F—H3F	0.9500
C3C—H3C	0.9500	C4F—C5F	1.3900
C4C—C5C	1.3900	C4F—H4F	0.9500
C4C—H4C	0.9500	C5F—C6F	1.3900
C5C—C6C	1.3900	C5F—Cl1F	1.744 (12)
C5C—Cl1C	1.724 (7)	C6F—C7F	1.3900
C6C—C7C	1.3900	C6F—H6F	0.9500
C6C—H6C	0.9500	C7F—H7F	0.9500
C7C—H7C	0.9500	N1F—N2F	1.22 (2)
N1C—N2C	1.269 (14)	N2F—C8F	1.424 (15)
N2C—C8C	1.452 (10)	C8F—C9F	1.3900
C8C—C9C	1.3900	C8F—C13F	1.3900
C8C—C13C	1.3900	C9F—C10F	1.3900
C9C—C10C	1.3900	C9F—H9F	0.9500
C9C—H9C	0.9500	C10F—C11F	1.3900
C10C—C11C	1.3900	C10F—H10F	0.9500
C10C—H10C	0.9500	C11F—C12F	1.3900
C11C—C12C	1.3900	C11F—H11F	0.9500
C11C—H11C	0.9500	C12F—C13F	1.3900
C12C—C13C	1.3900	C12F—H12F	0.9500
C12C—H12C	0.9500	C13F—H13F	0.9500
C13C—H13C	0.9500
N1A—C1A—C2A	109.2 (9)	C2D—C1D—N1D	104.9 (10)
N1A—C1A—C1B	107.6 (10)	C2D—C1D—C1C	115.4 (10)
C2A—C1A—C1B	110.9 (9)	N1D—C1D—C1C	106.3 (10)
N1A—C1A—H1A	109.7	C2D—C1D—H1D	110.0
C2A—C1A—H1A	109.7	N1D—C1D—H1D	110.0
C1B—C1A—H1A	109.7	C1C—C1D—H1D	110.0
C3A—C2A—C7A	120.0	C3D—C2D—C7D	120.0
C3A—C2A—C1A	118.8 (7)	C3D—C2D—C1D	123.6 (8)
C7A—C2A—C1A	121.2 (7)	C7D—C2D—C1D	116.3 (8)
C4A—C3A—C2A	120.0	C4D—C3D—C2D	120.0
C4A—C3A—H3A	120.0	C4D—C3D—H3D	120.0
C2A—C3A—H3A	120.0	C2D—C3D—H3D	120.0
C5A—C4A—C3A	120.0	C3D—C4D—C5D	120.0
C5A—C4A—H4A	120.0	C3D—C4D—H4D	120.0
C3A—C4A—H4A	120.0	C5D—C4D—H4D	120.0
C4A—C5A—C6A	120.0	C4D—C5D—C6D	120.0
C4A—C5A—Cl1A	120.9 (5)	C4D—C5D—Cl1D	115.4 (6)
C6A—C5A—Cl1A	119.1 (5)	C6D—C5D—Cl1D	124.6 (6)
C7A—C6A—C5A	120.0	C7D—C6D—C5D	120.0
C7A—C6A—H6A	120.0	C7D—C6D—H6D	120.0
C5A—C6A—H6A	120.0	C5D—C6D—H6D	120.0
C6A—C7A—C2A	120.0	C6D—C7D—C2D	120.0
C6A—C7A—H7A	120.0	C6D—C7D—H7D	120.0
C2A—C7A—H7A	120.0	C2D—C7D—H7D	120.0
N2A—N1A—C1A	119.3 (12)	N2D—N1D—C1D	114.2 (12)
N1A—N2A—C8A	118.3 (12)	N1D—N2D—C8D	113.5 (11)
C9A—C8A—C13A	120.0	C9D—C8D—C13D	120.0
C9A—C8A—N2A	124.8 (8)	C9D—C8D—N2D	123.2 (8)
C13A—C8A—N2A	115.1 (8)	C13D—C8D—N2D	116.7 (8)
C8A—C9A—C10A	120.0	C10D—C9D—C8D	120.0
C8A—C9A—H9A	120.0	C10D—C9D—H9D	120.0
C10A—C9A—H9A	120.0	C8D—C9D—H9D	120.0
C11A—C10A—C9A	120.0	C9D—C10D—C11D	120.0
C11A—C10A—H10A	120.0	C9D—C10D—H10D	120.0
C9A—C10A—H10A	120.0	C11D—C10D—H10D	120.0
C10A—C11A—C12A	120.0	C12D—C11D—C10D	120.0
C10A—C11A—H11A	120.0	C12D—C11D—H11D	120.0
C12A—C11A—H11A	120.0	C10D—C11D—H11D	120.0
C13A—C12A—C11A	120.0	C11D—C12D—C13D	120.0
C13A—C12A—H12A	120.0	C11D—C12D—H12D	120.0
C11A—C12A—H12A	120.0	C13D—C12D—H12D	120.0
C12A—C13A—C8A	120.0	C12D—C13D—C8D	120.0
C12A—C13A—H13A	120.0	C12D—C13D—H13D	120.0
C8A—C13A—H13A	120.0	C8D—C13D—H13D	120.0
N1B—C1B—C2B	107.8 (9)	N1E—C1E—C1F	104.1 (16)
N1B—C1B—C1A	107.0 (9)	N1E—C1E—C2E	113.0 (17)
C2B—C1B—C1A	119.6 (9)	C1F—C1E—C2E	111.4 (15)
N1B—C1B—H1B	107.3	N1E—C1E—H1E	109.4
C2B—C1B—H1B	107.3	C1F—C1E—H1E	109.4
C1A—C1B—H1B	107.3	C2E—C1E—H1E	109.4
C3B—C2B—C7B	120.0	C3E—C2E—C7E	120.0
C3B—C2B—C1B	121.5 (7)	C3E—C2E—C1E	110.0 (13)
C7B—C2B—C1B	118.5 (7)	C7E—C2E—C1E	129.8 (13)
C2B—C3B—C4B	120.0	C2E—C3E—C4E	120.0
C2B—C3B—H3B	120.0	C2E—C3E—H3E	120.0
C4B—C3B—H3B	120.0	C4E—C3E—H3E	120.0
C5B—C4B—C3B	120.0	C5E—C4E—C3E	120.0
C5B—C4B—H4B	120.0	C5E—C4E—H4E	120.0
C3B—C4B—H4B	120.0	C3E—C4E—H4E	120.0
C4B—C5B—C6B	120.0	C4E—C5E—C6E	120.0
C4B—C5B—Cl1B	119.0 (5)	C4E—C5E—Cl1E	123.1 (9)
C6B—C5B—Cl1B	121.0 (5)	C6E—C5E—Cl1E	116.5 (9)
C7B—C6B—C5B	120.0	C7E—C6E—C5E	120.0
C7B—C6B—H6B	120.0	C7E—C6E—H6E	120.0
C5B—C6B—H6B	120.0	C5E—C6E—H6E	120.0
C6B—C7B—C2B	120.0	C6E—C7E—C2E	120.0
C6B—C7B—H7B	120.0	C6E—C7E—H7E	120.0
C2B—C7B—H7B	120.0	C2E—C7E—H7E	120.0
N2B—N1B—C1B	115.0 (11)	N2E—N1E—C1E	115 (2)
N1B—N2B—C8B	115.5 (10)	N1E—N2E—C8E	111.2 (16)
C9B—C8B—C13B	120.0	C9E—C8E—C13E	120.0
C9B—C8B—N2B	123.0 (7)	C9E—C8E—N2E	120.9 (11)
C13B—C8B—N2B	117.0 (7)	C13E—C8E—N2E	117.7 (11)
C8B—C9B—C10B	120.0	C10E—C9E—C8E	120.0
C8B—C9B—H9B	120.0	C10E—C9E—H9E	120.0
C10B—C9B—H9B	120.0	C8E—C9E—H9E	120.0
C11B—C10B—C9B	120.0	C9E—C10E—C11E	120.0
C11B—C10B—H10B	120.0	C9E—C10E—H10E	120.0
C9B—C10B—H10B	120.0	C11E—C10E—H10E	120.0
C10B—C11B—C12B	120.0	C12E—C11E—C10E	120.0
C10B—C11B—H11B	120.0	C12E—C11E—H11E	120.0
C12B—C11B—H11B	120.0	C10E—C11E—H11E	120.0
C11B—C12B—C13B	120.0	C11E—C12E—C13E	120.0
C11B—C12B—H12B	120.0	C11E—C12E—H12E	120.0
C13B—C12B—H12B	120.0	C13E—C12E—H12E	120.0
C12B—C13B—C8B	120.0	C12E—C13E—C8E	120.0
C12B—C13B—H13B	120.0	C12E—C13E—H13E	120.0
C8B—C13B—H13B	120.0	C8E—C13E—H13E	120.0
N1C—C1C—C2C	109.6 (10)	N1F—C1F—C2F	105.0 (15)
N1C—C1C—C1D	104.8 (10)	N1F—C1F—C1E	106.6 (15)
C2C—C1C—C1D	110.5 (9)	C2F—C1F—C1E	118.9 (15)
N1C—C1C—H1C	110.6	N1F—C1F—H1F	108.7
C2C—C1C—H1C	110.6	C2F—C1F—H1F	108.7
C1D—C1C—H1C	110.6	C1E—C1F—H1F	108.7
C3C—C2C—C7C	120.0	C3F—C2F—C7F	120.0
C3C—C2C—C1C	116.9 (8)	C3F—C2F—C1F	123.0 (13)
C7C—C2C—C1C	122.7 (8)	C7F—C2F—C1F	116.9 (13)
C4C—C3C—C2C	120.0	C2F—C3F—C4F	120.0
C4C—C3C—H3C	120.0	C2F—C3F—H3F	120.0
C2C—C3C—H3C	120.0	C4F—C3F—H3F	120.0
C3C—C4C—C5C	120.0	C5F—C4F—C3F	120.0
C3C—C4C—H4C	120.0	C5F—C4F—H4F	120.0
C5C—C4C—H4C	120.0	C3F—C4F—H4F	120.0
C6C—C5C—C4C	120.0	C6F—C5F—C4F	120.0
C6C—C5C—Cl1C	119.2 (6)	C6F—C5F—Cl1F	120.3 (9)
C4C—C5C—Cl1C	120.7 (6)	C4F—C5F—Cl1F	119.6 (9)
C7C—C6C—C5C	120.0	C5F—C6F—C7F	120.0
C7C—C6C—H6C	120.0	C5F—C6F—H6F	120.0
C5C—C6C—H6C	120.0	C7F—C6F—H6F	120.0
C6C—C7C—C2C	120.0	C6F—C7F—C2F	120.0
C6C—C7C—H7C	120.0	C6F—C7F—H7F	120.0
C2C—C7C—H7C	120.0	C2F—C7F—H7F	120.0
N2C—N1C—C1C	112.8 (11)	N2F—N1F—C1F	101.7 (19)
N1C—N2C—C8C	113.9 (10)	N1F—N2F—C8F	101.6 (16)
C9C—C8C—C13C	120.0	C9F—C8F—C13F	120.0
C9C—C8C—N2C	127.7 (7)	C9F—C8F—N2F	123.9 (12)
C13C—C8C—N2C	112.3 (7)	C13F—C8F—N2F	116.0 (12)
C10C—C9C—C8C	120.0	C8F—C9F—C10F	120.0
C10C—C9C—H9C	120.0	C8F—C9F—H9F	120.0
C8C—C9C—H9C	120.0	C10F—C9F—H9F	120.0
C9C—C10C—C11C	120.0	C11F—C10F—C9F	120.0
C9C—C10C—H10C	120.0	C11F—C10F—H10F	120.0
C11C—C10C—H10C	120.0	C9F—C10F—H10F	120.0
C12C—C11C—C10C	120.0	C10F—C11F—C12F	120.0
C12C—C11C—H11C	120.0	C10F—C11F—H11F	120.0
C10C—C11C—H11C	120.0	C12F—C11F—H11F	120.0
C13C—C12C—C11C	120.0	C11F—C12F—C13F	120.0
C13C—C12C—H12C	120.0	C11F—C12F—H12F	120.0
C11C—C12C—H12C	120.0	C13F—C12F—H12F	120.0
C12C—C13C—C8C	120.0	C12F—C13F—C8F	120.0
C12C—C13C—H13C	120.0	C12F—C13F—H13F	120.0
C8C—C13C—H13C	120.0	C8F—C13F—H13F	120.0
N1A—C1A—C2A—C3A	−123.3 (10)	N1C—C1C—C1D—N1D	−71.7 (12)
C1B—C1A—C2A—C3A	118.3 (9)	C2C—C1C—C1D—N1D	170.3 (11)
N1A—C1A—C2A—C7A	55.1 (13)	N1D—C1D—C2D—C3D	124.1 (12)
C1B—C1A—C2A—C7A	−63.3 (12)	C1C—C1D—C2D—C3D	−119.3 (12)
C7A—C2A—C3A—C4A	0.0	N1D—C1D—C2D—C7D	−59.3 (13)
C1A—C2A—C3A—C4A	178.4 (10)	C1C—C1D—C2D—C7D	57.3 (13)
C2A—C3A—C4A—C5A	0.0	C7D—C2D—C3D—C4D	0.0
C3A—C4A—C5A—C6A	0.0	C1D—C2D—C3D—C4D	176.4 (13)
C3A—C4A—C5A—Cl1A	178.0 (9)	C2D—C3D—C4D—C5D	0.0
C4A—C5A—C6A—C7A	0.0	C3D—C4D—C5D—C6D	0.0
Cl1A—C5A—C6A—C7A	−178.0 (8)	C3D—C4D—C5D—Cl1D	−179.3 (10)
C5A—C6A—C7A—C2A	0.0	C4D—C5D—C6D—C7D	0.0
C3A—C2A—C7A—C6A	0.0	Cl1D—C5D—C6D—C7D	179.2 (11)
C1A—C2A—C7A—C6A	−178.4 (10)	C5D—C6D—C7D—C2D	0.0
C2A—C1A—N1A—N2A	131.5 (13)	C3D—C2D—C7D—C6D	0.0
C1B—C1A—N1A—N2A	−108.0 (15)	C1D—C2D—C7D—C6D	−176.6 (12)
C1A—N1A—N2A—C8A	−172.3 (11)	C2D—C1D—N1D—N2D	−121.6 (15)
N1A—N2A—C8A—C9A	−2.7 (17)	C1C—C1D—N1D—N2D	115.7 (15)
N1A—N2A—C8A—C13A	−178.6 (10)	C1D—N1D—N2D—C8D	−179.1 (12)
C13A—C8A—C9A—C10A	0.0	N1D—N2D—C8D—C9D	2.6 (19)
N2A—C8A—C9A—C10A	−175.7 (12)	N1D—N2D—C8D—C13D	−175.1 (12)
C8A—C9A—C10A—C11A	0.0	C13D—C8D—C9D—C10D	0.0
C9A—C10A—C11A—C12A	0.0	N2D—C8D—C9D—C10D	−177.7 (12)
C10A—C11A—C12A—C13A	0.0	C8D—C9D—C10D—C11D	0.0
C11A—C12A—C13A—C8A	0.0	C9D—C10D—C11D—C12D	0.0
C9A—C8A—C13A—C12A	0.0	C10D—C11D—C12D—C13D	0.0
N2A—C8A—C13A—C12A	176.1 (11)	C11D—C12D—C13D—C8D	0.0
N1A—C1A—C1B—N1B	68.5 (12)	C9D—C8D—C13D—C12D	0.0
C2A—C1A—C1B—N1B	−172.1 (10)	N2D—C8D—C13D—C12D	177.8 (11)
N1A—C1A—C1B—C2B	−168.6 (11)	N1E—C1E—C2E—C3E	126.9 (19)
C2A—C1A—C1B—C2B	−49.2 (13)	C1F—C1E—C2E—C3E	−116.4 (16)
N1B—C1B—C2B—C3B	−130.1 (9)	N1E—C1E—C2E—C7E	−48 (3)
C1A—C1B—C2B—C3B	107.4 (11)	C1F—C1E—C2E—C7E	69 (2)
N1B—C1B—C2B—C7B	49.8 (11)	C7E—C2E—C3E—C4E	0.0
C1A—C1B—C2B—C7B	−72.7 (11)	C1E—C2E—C3E—C4E	−175.5 (17)
C7B—C2B—C3B—C4B	0.0	C2E—C3E—C4E—C5E	0.0
C1B—C2B—C3B—C4B	179.9 (9)	C3E—C4E—C5E—C6E	0.0
C2B—C3B—C4B—C5B	0.0	C3E—C4E—C5E—Cl1E	−172.7 (18)
C3B—C4B—C5B—C6B	0.0	C4E—C5E—C6E—C7E	0.0
C3B—C4B—C5B—Cl1B	−179.9 (7)	Cl1E—C5E—C6E—C7E	173.2 (17)
C4B—C5B—C6B—C7B	0.0	C5E—C6E—C7E—C2E	0.0
Cl1B—C5B—C6B—C7B	179.9 (7)	C3E—C2E—C7E—C6E	0.0
C5B—C6B—C7B—C2B	0.0	C1E—C2E—C7E—C6E	175 (2)
C3B—C2B—C7B—C6B	0.0	C1F—C1E—N1E—N2E	116 (2)
C1B—C2B—C7B—C6B	−180.0 (8)	C2E—C1E—N1E—N2E	−123 (3)
C2B—C1B—N1B—N2B	118.5 (13)	C1E—N1E—N2E—C8E	176 (2)
C1A—C1B—N1B—N2B	−111.6 (13)	N1E—N2E—C8E—C9E	−22 (3)
C1B—N1B—N2B—C8B	−179.1 (10)	N1E—N2E—C8E—C13E	171.3 (18)
N1B—N2B—C8B—C9B	−9.6 (16)	C13E—C8E—C9E—C10E	0.0
N1B—N2B—C8B—C13B	170.0 (10)	N2E—C8E—C9E—C10E	−166.0 (19)
C13B—C8B—C9B—C10B	0.0	C8E—C9E—C10E—C11E	0.0
N2B—C8B—C9B—C10B	179.6 (10)	C9E—C10E—C11E—C12E	0.0
C8B—C9B—C10B—C11B	0.0	C10E—C11E—C12E—C13E	0.0
C9B—C10B—C11B—C12B	0.0	C11E—C12E—C13E—C8E	0.0
C10B—C11B—C12B—C13B	0.0	C9E—C8E—C13E—C12E	0.0
C11B—C12B—C13B—C8B	0.0	N2E—C8E—C13E—C12E	166.4 (19)
C9B—C8B—C13B—C12B	0.0	N1E—C1E—C1F—N1F	−176 (2)
N2B—C8B—C13B—C12B	−179.6 (10)	C2E—C1E—C1F—N1F	62 (2)
N1C—C1C—C2C—C3C	127.7 (10)	N1E—C1E—C1F—C2F	−57 (2)
C1D—C1C—C2C—C3C	−117.3 (10)	C2E—C1E—C1F—C2F	−179.5 (19)
N1C—C1C—C2C—C7C	−45.3 (13)	N1F—C1F—C2F—C3F	−123.5 (16)
C1D—C1C—C2C—C7C	69.7 (11)	C1E—C1F—C2F—C3F	117.4 (17)
C7C—C2C—C3C—C4C	0.0	N1F—C1F—C2F—C7F	60 (2)
C1C—C2C—C3C—C4C	−173.2 (9)	C1E—C1F—C2F—C7F	−59 (2)
C2C—C3C—C4C—C5C	0.0	C7F—C2F—C3F—C4F	0.0
C3C—C4C—C5C—C6C	0.0	C1F—C2F—C3F—C4F	−176.4 (16)
C3C—C4C—C5C—Cl1C	177.4 (8)	C2F—C3F—C4F—C5F	0.0
C4C—C5C—C6C—C7C	0.0	C3F—C4F—C5F—C6F	0.0
Cl1C—C5C—C6C—C7C	−177.5 (7)	C3F—C4F—C5F—Cl1F	−178.2 (13)
C5C—C6C—C7C—C2C	0.0	C4F—C5F—C6F—C7F	0.0
C3C—C2C—C7C—C6C	0.0	Cl1F—C5F—C6F—C7F	178.2 (13)
C1C—C2C—C7C—C6C	172.8 (9)	C5F—C6F—C7F—C2F	0.0
C2C—C1C—N1C—N2C	−124.0 (13)	C3F—C2F—C7F—C6F	0.0
C1D—C1C—N1C—N2C	117.5 (12)	C1F—C2F—C7F—C6F	176.6 (15)
C1C—N1C—N2C—C8C	−179.1 (10)	C2F—C1F—N1F—N2F	102 (2)
N1C—N2C—C8C—C9C	0.9 (16)	C1E—C1F—N1F—N2F	−131 (2)
N1C—N2C—C8C—C13C	−178.9 (9)	C1F—N1F—N2F—C8F	173.6 (16)
C13C—C8C—C9C—C10C	0.0	N1F—N2F—C8F—C9F	10 (3)
N2C—C8C—C9C—C10C	−179.8 (11)	N1F—N2F—C8F—C13F	−173.4 (17)
C8C—C9C—C10C—C11C	0.0	C13F—C8F—C9F—C10F	0.0
C9C—C10C—C11C—C12C	0.0	N2F—C8F—C9F—C10F	176 (2)
C10C—C11C—C12C—C13C	0.0	C8F—C9F—C10F—C11F	0.0
C11C—C12C—C13C—C8C	0.0	C9F—C10F—C11F—C12F	0.0
C9C—C8C—C13C—C12C	0.0	C10F—C11F—C12F—C13F	0.0
N2C—C8C—C13C—C12C	179.8 (10)	C11F—C12F—C13F—C8F	0.0
N1C—C1C—C1D—C2D	172.5 (11)	C9F—C8F—C13F—C12F	0.0
C2C—C1C—C1D—C2D	54.5 (13)	N2F—C8F—C13F—C12F	−176.5 (18)

1,1'-[1,2-Bis(4-chlorophenyl)ethane-1,2-diyl]bis(phenyldiazene) (IId)

Crystal data

C26H20Cl2N4	F(000) = 952
Mr = 459.36	Dx = 1.317 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 22.657 (10) Å	Cell parameters from 3065 reflections
b = 5.4399 (18) Å	θ = 2.2–30.3°
c = 19.086 (6) Å	µ = 0.30 mm^−1
β = 99.967 (7)°	T = 100 K
V = 2316.9 (15) Å^3	Needle, yellow
Z = 4	0.50 × 0.06 × 0.05 mm

Data collection

Rigaku AFC12 diffractometer	2189 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm^-1	Rint = 0.030
profile data from ω–scans	θmax = 30.3°, θmin = 2.6°
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012)	h = −29→23
Tmin = 0.797, Tmax = 0.985	k = −7→7
8691 measured reflections	l = −26→26
3064 independent reflections

Refinement

Refinement on F^2	861 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.141	w = 1/[σ^2(Fo^2) + (0.0546P)^2 + 0.7288P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.004
3064 reflections	Δρmax = 0.21 e Å^−3
344 parameters	Δρmin = −0.17 e Å^−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	Occ. (<1)
C1A	0.2560 (2)	0.8602 (10)	0.4658 (3)	0.0335 (6)	0.3872 (15)
H1A	0.266805	1.021496	0.489719	0.040*	0.3872 (15)
N1A	0.1905 (3)	0.8497 (18)	0.4411 (5)	0.0316 (14)	0.3872 (15)
N2A	0.1627 (3)	1.029 (2)	0.4592 (7)	0.0387 (19)	0.3872 (15)
C2A	0.0987 (2)	1.0154 (13)	0.4364 (4)	0.0373 (15)	0.3872 (15)
C3A	0.0661 (3)	1.2216 (12)	0.4495 (4)	0.0458 (18)	0.3872 (15)
H3A	0.085878	1.357083	0.474880	0.055*	0.3872 (15)
C4A	0.0046 (3)	1.2298 (11)	0.4256 (5)	0.0505 (16)	0.3872 (15)
H4A	−0.017655	1.370765	0.434551	0.061*	0.3872 (15)
C5A	−0.0243 (2)	1.0316 (13)	0.3884 (4)	0.078 (3)	0.3872 (15)
H5A	−0.066312	1.037165	0.372072	0.093*	0.3872 (15)
C6A	0.0083 (3)	0.8253 (12)	0.3753 (4)	0.0561 (18)	0.3872 (15)
H6A	−0.011436	0.689881	0.349922	0.067*	0.3872 (15)
C7A	0.0698 (3)	0.8172 (11)	0.3992 (4)	0.053 (3)	0.3872 (15)
H7A	0.092097	0.676195	0.390251	0.064*	0.3872 (15)
C8A	0.2844 (3)	0.8418 (13)	0.4001 (3)	0.0319 (16)	0.3872 (15)
C9A	0.2717 (4)	0.6441 (12)	0.3539 (3)	0.0317 (13)	0.3872 (15)
H9A	0.244095	0.521363	0.362868	0.038*	0.3872 (15)
C10A	0.2992 (4)	0.6259 (13)	0.2944 (3)	0.0306 (19)	0.3872 (15)
H10A	0.290483	0.490800	0.262791	0.037*	0.3872 (15)
C11A	0.3396 (3)	0.8055 (15)	0.2812 (3)	0.0361 (13)	0.3872 (15)
C12A	0.3523 (3)	1.0032 (14)	0.3275 (4)	0.036 (2)	0.3872 (15)
H12A	0.379898	1.125937	0.318505	0.044*	0.3872 (15)
C13A	0.3248 (3)	1.0214 (13)	0.3870 (4)	0.0315 (12)	0.3872 (15)
H13A	0.333510	1.156503	0.418582	0.038*	0.3872 (15)
Cl1A	0.3769 (3)	0.7838 (15)	0.2129 (3)	0.0646 (13)	0.3872 (15)
C1B	0.2723 (2)	0.6498 (10)	0.5200 (3)	0.0335 (6)	0.3872 (15)
H1B	0.252509	0.495925	0.499115	0.040*	0.3872 (15)
N1B	0.24731 (18)	0.7122 (8)	0.5845 (2)	0.0341 (9)	0.3872 (15)
N2B	0.2068 (2)	0.5765 (10)	0.5955 (3)	0.0328 (11)	0.3872 (15)
C2B	0.18189 (14)	0.6356 (6)	0.65794 (14)	0.0354 (9)	0.3872 (15)
C3B	0.14065 (15)	0.4667 (5)	0.67521 (17)	0.0431 (19)	0.3872 (15)
H3B	0.130853	0.324851	0.646533	0.052*	0.3872 (15)
C4B	0.11375 (17)	0.5055 (6)	0.7344 (2)	0.0563 (13)	0.3872 (15)
H4B	0.085565	0.390077	0.746232	0.068*	0.3872 (15)
C5B	0.12809 (18)	0.7131 (7)	0.77638 (17)	0.051 (3)	0.3872 (15)
H5B	0.109703	0.739569	0.816860	0.061*	0.3872 (15)
C6B	0.16933 (16)	0.8819 (6)	0.75911 (16)	0.0433 (10)	0.3872 (15)
H6B	0.179128	1.023837	0.787789	0.052*	0.3872 (15)
C7B	0.19623 (13)	0.8432 (6)	0.69989 (17)	0.039 (2)	0.3872 (15)
H7B	0.224417	0.958615	0.688089	0.046*	0.3872 (15)
C8B	0.33890 (10)	0.5998 (6)	0.54131 (18)	0.0321 (13)	0.3872 (15)
C9B	0.37486 (12)	0.7636 (5)	0.58553 (18)	0.0387 (9)	0.3872 (15)
H9B	0.358182	0.910966	0.600339	0.046*	0.3872 (15)
C10B	0.43524 (12)	0.7118 (5)	0.60807 (17)	0.039 (2)	0.3872 (15)
H10B	0.459820	0.823703	0.638290	0.046*	0.3872 (15)
C11B	0.45965 (10)	0.4961 (6)	0.58640 (18)	0.0412 (9)	0.3872 (15)
C12B	0.42368 (14)	0.3323 (5)	0.54218 (19)	0.0407 (15)	0.3872 (15)
H12B	0.440366	0.184964	0.527366	0.049*	0.3872 (15)
C13B	0.36331 (13)	0.3842 (6)	0.51963 (18)	0.0361 (10)	0.3872 (15)
H13B	0.338728	0.272223	0.489414	0.043*	0.3872 (15)
Cl1B	0.53413 (7)	0.4299 (4)	0.61552 (9)	0.0560 (6)	0.3872 (15)
C1C	0.2425 (3)	0.8584 (15)	0.4751 (5)	0.0335 (6)	0.226 (3)
H1C	0.253229	1.018067	0.499987	0.040*	0.226 (3)
N1C	0.1773 (5)	0.839 (3)	0.4496 (9)	0.032 (3)	0.226 (3)
N2C	0.1497 (5)	1.028 (3)	0.4619 (11)	0.030 (2)	0.226 (3)
C2C	0.0872 (4)	1.019 (2)	0.4313 (7)	0.037 (3)	0.226 (3)
C3C	0.0506 (5)	1.190 (2)	0.4570 (7)	0.041 (3)	0.226 (3)
H3C	0.067208	1.300989	0.493527	0.050*	0.226 (3)
C4C	−0.0102 (4)	1.198 (2)	0.4291 (8)	0.045 (2)	0.226 (3)
H4C	−0.035240	1.315177	0.446638	0.054*	0.226 (3)
C5C	−0.0345 (4)	1.036 (2)	0.3756 (8)	0.078 (3)	0.226 (3)
H5C	−0.076091	1.041555	0.356587	0.093*	0.226 (3)
C6C	0.0021 (6)	0.865 (2)	0.3500 (5)	0.059 (3)	0.226 (3)
H6C	−0.014496	0.753742	0.313425	0.071*	0.226 (3)
C7C	0.0629 (5)	0.856 (2)	0.3778 (6)	0.042 (3)	0.226 (3)
H7C	0.087952	0.739549	0.360314	0.050*	0.226 (3)
C8C	0.2744 (6)	0.826 (3)	0.4121 (6)	0.034 (3)	0.226 (3)
C9C	0.2663 (7)	0.619 (2)	0.3687 (6)	0.042 (3)	0.226 (3)
H9C	0.240773	0.490356	0.378766	0.050*	0.226 (3)
C10C	0.2956 (8)	0.601 (2)	0.3107 (6)	0.041 (3)	0.226 (3)
H10C	0.290082	0.459898	0.281044	0.049*	0.226 (3)
C11C	0.3329 (7)	0.790 (3)	0.2960 (6)	0.042 (2)	0.226 (3)
C12C	0.3410 (6)	0.997 (2)	0.3393 (7)	0.037 (2)	0.226 (3)
H12C	0.366535	1.126037	0.329250	0.044*	0.226 (3)
C13C	0.3117 (6)	1.015 (2)	0.3973 (7)	0.039 (3)	0.226 (3)
H13C	0.317226	1.156500	0.426972	0.046*	0.226 (3)
Cl1C	0.3681 (5)	0.756 (3)	0.2176 (5)	0.065 (2)	0.226 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0335 (18)	0.0306 (10)	0.0358 (14)	−0.0016 (14)	0.0044 (12)	−0.0045 (10)
N1A	0.030 (2)	0.033 (3)	0.033 (3)	0.001 (2)	0.007 (2)	−0.0011 (19)
N2A	0.036 (3)	0.041 (3)	0.038 (3)	0.005 (3)	0.004 (3)	−0.002 (3)
C2A	0.037 (3)	0.045 (3)	0.030 (3)	0.005 (2)	0.005 (2)	0.002 (2)
C3A	0.039 (3)	0.053 (4)	0.043 (3)	0.008 (3)	0.000 (3)	−0.005 (3)
C4A	0.041 (4)	0.056 (4)	0.053 (3)	0.010 (3)	0.003 (3)	0.002 (3)
C5A	0.049 (4)	0.073 (4)	0.105 (6)	−0.009 (3)	−0.002 (3)	−0.013 (3)
C6A	0.043 (3)	0.056 (3)	0.067 (5)	−0.010 (2)	0.007 (3)	−0.007 (3)
C7A	0.045 (3)	0.058 (5)	0.057 (5)	−0.001 (3)	0.010 (3)	−0.013 (5)
C8A	0.028 (3)	0.038 (4)	0.028 (3)	0.000 (2)	0.002 (2)	0.000 (2)
C9A	0.038 (2)	0.026 (2)	0.030 (3)	−0.0067 (19)	0.001 (2)	0.002 (2)
C10A	0.037 (3)	0.032 (4)	0.018 (3)	0.002 (3)	−0.007 (2)	0.000 (3)
C11A	0.037 (3)	0.044 (3)	0.026 (3)	0.009 (2)	0.002 (2)	0.013 (2)
C12A	0.038 (4)	0.039 (4)	0.034 (4)	−0.003 (3)	0.011 (3)	0.002 (3)
C13A	0.032 (3)	0.027 (2)	0.034 (3)	−0.002 (2)	0.001 (2)	−0.006 (2)
Cl1A	0.0717 (16)	0.068 (3)	0.0609 (18)	0.0156 (17)	0.0302 (14)	0.0148 (14)
C1B	0.0335 (18)	0.0306 (10)	0.0358 (14)	−0.0016 (14)	0.0044 (12)	−0.0045 (10)
N1B	0.031 (2)	0.037 (2)	0.0333 (19)	0.0035 (16)	0.0029 (16)	−0.0026 (16)
N2B	0.028 (2)	0.039 (3)	0.030 (2)	0.0005 (19)	−0.0005 (16)	−0.0038 (19)
C2B	0.0329 (19)	0.040 (2)	0.0319 (19)	0.0134 (16)	0.0022 (15)	0.0069 (17)
C3B	0.053 (4)	0.028 (3)	0.050 (4)	0.001 (3)	0.014 (3)	0.005 (3)
C4B	0.073 (3)	0.041 (2)	0.062 (3)	0.005 (2)	0.029 (2)	0.014 (2)
C5B	0.043 (6)	0.043 (4)	0.066 (6)	0.010 (4)	0.007 (5)	0.018 (3)
C6B	0.055 (2)	0.038 (2)	0.035 (2)	0.0112 (18)	0.0016 (18)	−0.0046 (18)
C7B	0.046 (4)	0.032 (3)	0.035 (4)	0.007 (3)	0.000 (3)	0.004 (3)
C8B	0.032 (2)	0.037 (3)	0.028 (2)	−0.001 (2)	0.0047 (19)	0.000 (3)
C9B	0.0394 (19)	0.0283 (19)	0.044 (2)	0.0018 (14)	−0.0056 (16)	−0.0034 (17)
C10B	0.038 (3)	0.035 (3)	0.039 (5)	−0.005 (2)	−0.003 (3)	0.012 (3)
C11B	0.0356 (19)	0.044 (2)	0.042 (2)	0.0027 (15)	0.0033 (16)	0.0149 (19)
C12B	0.037 (2)	0.039 (3)	0.046 (3)	0.006 (2)	0.008 (2)	0.005 (2)
C13B	0.042 (2)	0.035 (3)	0.032 (2)	−0.0008 (17)	0.0076 (17)	−0.0011 (18)
Cl1B	0.0347 (7)	0.0695 (11)	0.0610 (11)	0.0059 (7)	0.0004 (7)	0.0198 (9)
C1C	0.0335 (18)	0.0306 (10)	0.0358 (14)	−0.0016 (14)	0.0044 (12)	−0.0045 (10)
N1C	0.036 (4)	0.029 (4)	0.033 (6)	−0.004 (4)	0.008 (4)	0.000 (4)
N2C	0.037 (4)	0.029 (5)	0.025 (4)	−0.004 (3)	0.006 (4)	−0.005 (4)
C2C	0.032 (4)	0.039 (5)	0.038 (5)	−0.003 (3)	−0.002 (3)	0.005 (4)
C3C	0.036 (5)	0.035 (4)	0.054 (5)	−0.014 (3)	0.010 (4)	−0.003 (4)
C4C	0.031 (4)	0.040 (4)	0.068 (5)	−0.012 (3)	0.019 (4)	0.001 (4)
C5C	0.049 (4)	0.073 (4)	0.105 (6)	−0.009 (3)	−0.002 (3)	−0.013 (3)
C6C	0.053 (5)	0.066 (6)	0.054 (7)	−0.015 (4)	0.000 (4)	−0.006 (5)
C7C	0.052 (4)	0.035 (6)	0.038 (5)	−0.012 (4)	0.003 (4)	0.007 (4)
C8C	0.029 (6)	0.040 (5)	0.031 (5)	−0.001 (4)	−0.002 (4)	0.006 (4)
C9C	0.057 (6)	0.038 (5)	0.025 (5)	0.002 (4)	−0.008 (4)	0.010 (3)
C10C	0.062 (6)	0.025 (5)	0.031 (6)	0.005 (4)	−0.007 (4)	0.008 (4)
C11C	0.062 (7)	0.041 (5)	0.022 (4)	0.012 (4)	0.006 (4)	0.010 (4)
C12C	0.036 (5)	0.031 (4)	0.045 (6)	−0.001 (4)	0.010 (4)	0.008 (4)
C13C	0.025 (6)	0.041 (5)	0.049 (6)	0.000 (4)	0.003 (4)	−0.004 (4)
Cl1C	0.084 (4)	0.062 (3)	0.044 (3)	−0.004 (2)	−0.002 (3)	−0.004 (3)

Geometric parameters (Å, º)

C1A—N1A	1.479 (6)	C6B—H6B	0.9500
C1A—C8A	1.508 (5)	C7B—H7B	0.9500
C1A—C1B	1.545 (6)	C8B—C9B	1.3900
C1A—H1A	1.0000	C8B—C13B	1.3900
N1A—N2A	1.242 (7)	C9B—C10B	1.3900
N2A—C2A	1.442 (6)	C9B—H9B	0.9500
C2A—C3A	1.3900	C10B—C11B	1.3900
C2A—C7A	1.3900	C10B—H10B	0.9500
C3A—C4A	1.3900	C11B—C12B	1.3900
C3A—H3A	0.9500	C11B—Cl1B	1.721 (3)
C4A—C5A	1.3900	C12B—C13B	1.3900
C4A—H4A	0.9500	C12B—H12B	0.9500
C5A—C6A	1.3900	C13B—H13B	0.9500
C5A—H5A	0.9500	C1C—N1C	1.475 (11)
C6A—C7A	1.3900	C1C—C8C	1.517 (8)
C6A—H6A	0.9500	C1C—C1C^i	1.517 (13)
C7A—H7A	0.9500	C1C—H1C	1.0000
C8A—C9A	1.3900	N1C—N2C	1.245 (12)
C8A—C13A	1.3900	N2C—C2C	1.436 (10)
C9A—C10A	1.3900	C2C—C3C	1.3900
C9A—H9A	0.9500	C2C—C7C	1.3900
C10A—C11A	1.3900	C3C—C4C	1.3900
C10A—H10A	0.9500	C3C—H3C	0.9500
C11A—C12A	1.3900	C4C—C5C	1.3900
C11A—Cl1A	1.678 (7)	C4C—H4C	0.9500
C12A—C13A	1.3900	C5C—C6C	1.3900
C12A—H12A	0.9500	C5C—H5C	0.9500
C13A—H13A	0.9500	C6C—C7C	1.3900
C1B—N1B	1.480 (6)	C6C—H6C	0.9500
C1B—C8B	1.517 (5)	C7C—H7C	0.9500
C1B—H1B	1.0000	C8C—C9C	1.3900
N1B—N2B	1.224 (5)	C8C—C13C	1.3900
N2B—C2B	1.441 (5)	C9C—C10C	1.3900
C2B—C3B	1.3900	C9C—H9C	0.9500
C2B—C7B	1.3900	C10C—C11C	1.3900
C3B—C4B	1.3900	C10C—H10C	0.9500
C3B—H3B	0.9500	C11C—C12C	1.3900
C4B—C5B	1.3900	C11C—Cl1C	1.822 (12)
C4B—H4B	0.9500	C12C—C13C	1.3900
C5B—C6B	1.3900	C12C—H12C	0.9500
C5B—H5B	0.9500	C13C—H13C	0.9500
C6B—C7B	1.3900
N1A—C1A—C8A	106.4 (5)	C7B—C6B—H6B	120.0
N1A—C1A—C1B	107.2 (5)	C6B—C7B—C2B	120.0
C8A—C1A—C1B	114.9 (5)	C6B—C7B—H7B	120.0
N1A—C1A—H1A	109.4	C2B—C7B—H7B	120.0
C8A—C1A—H1A	109.4	C9B—C8B—C13B	120.0
C1B—C1A—H1A	109.4	C9B—C8B—C1B	119.9 (3)
N2A—N1A—C1A	114.2 (7)	C13B—C8B—C1B	120.0 (3)
N1A—N2A—C2A	114.0 (7)	C10B—C9B—C8B	120.0
C3A—C2A—C7A	120.0	C10B—C9B—H9B	120.0
C3A—C2A—N2A	116.2 (5)	C8B—C9B—H9B	120.0
C7A—C2A—N2A	123.7 (5)	C11B—C10B—C9B	120.0
C2A—C3A—C4A	120.0	C11B—C10B—H10B	120.0
C2A—C3A—H3A	120.0	C9B—C10B—H10B	120.0
C4A—C3A—H3A	120.0	C10B—C11B—C12B	120.0
C3A—C4A—C5A	120.0	C10B—C11B—Cl1B	119.93 (19)
C3A—C4A—H4A	120.0	C12B—C11B—Cl1B	120.06 (19)
C5A—C4A—H4A	120.0	C13B—C12B—C11B	120.0
C6A—C5A—C4A	120.0	C13B—C12B—H12B	120.0
C6A—C5A—H5A	120.0	C11B—C12B—H12B	120.0
C4A—C5A—H5A	120.0	C12B—C13B—C8B	120.0
C5A—C6A—C7A	120.0	C12B—C13B—H13B	120.0
C5A—C6A—H6A	120.0	C8B—C13B—H13B	120.0
C7A—C6A—H6A	120.0	N1C—C1C—C8C	108.5 (9)
C6A—C7A—C2A	120.0	N1C—C1C—C1C^i	104.7 (10)
C6A—C7A—H7A	120.0	C8C—C1C—C1C^i	108.7 (9)
C2A—C7A—H7A	120.0	N1C—C1C—H1C	111.5
C9A—C8A—C13A	120.0	C8C—C1C—H1C	111.5
C9A—C8A—C1A	120.5 (4)	C1C^i—C1C—H1C	111.5
C13A—C8A—C1A	119.5 (4)	N2C—N1C—C1C	112.7 (11)
C8A—C9A—C10A	120.0	N1C—N2C—C2C	112.9 (11)
C8A—C9A—H9A	120.0	C3C—C2C—C7C	120.0
C10A—C9A—H9A	120.0	C3C—C2C—N2C	116.2 (8)
C11A—C10A—C9A	120.0	C7C—C2C—N2C	123.8 (8)
C11A—C10A—H10A	120.0	C2C—C3C—C4C	120.0
C9A—C10A—H10A	120.0	C2C—C3C—H3C	120.0
C10A—C11A—C12A	120.0	C4C—C3C—H3C	120.0
C10A—C11A—Cl1A	121.8 (4)	C3C—C4C—C5C	120.0
C12A—C11A—Cl1A	118.1 (4)	C3C—C4C—H4C	120.0
C13A—C12A—C11A	120.0	C5C—C4C—H4C	120.0
C13A—C12A—H12A	120.0	C6C—C5C—C4C	120.0
C11A—C12A—H12A	120.0	C6C—C5C—H5C	120.0
C12A—C13A—C8A	120.0	C4C—C5C—H5C	120.0
C12A—C13A—H13A	120.0	C5C—C6C—C7C	120.0
C8A—C13A—H13A	120.0	C5C—C6C—H6C	120.0
N1B—C1B—C8B	108.9 (4)	C7C—C6C—H6C	120.0
N1B—C1B—C1A	107.8 (4)	C6C—C7C—C2C	120.0
C8B—C1B—C1A	115.1 (4)	C6C—C7C—H7C	120.0
N1B—C1B—H1B	108.3	C2C—C7C—H7C	120.0
C8B—C1B—H1B	108.3	C9C—C8C—C13C	120.0
C1A—C1B—H1B	108.3	C9C—C8C—C1C	122.2 (7)
N2B—N1B—C1B	114.3 (4)	C13C—C8C—C1C	117.7 (7)
N1B—N2B—C2B	114.8 (4)	C10C—C9C—C8C	120.0
C3B—C2B—C7B	120.0	C10C—C9C—H9C	120.0
C3B—C2B—N2B	115.1 (3)	C8C—C9C—H9C	120.0
C7B—C2B—N2B	124.9 (3)	C9C—C10C—C11C	120.0
C2B—C3B—C4B	120.0	C9C—C10C—H10C	120.0
C2B—C3B—H3B	120.0	C11C—C10C—H10C	120.0
C4B—C3B—H3B	120.0	C10C—C11C—C12C	120.0
C3B—C4B—C5B	120.0	C10C—C11C—Cl1C	117.3 (7)
C3B—C4B—H4B	120.0	C12C—C11C—Cl1C	122.7 (7)
C5B—C4B—H4B	120.0	C13C—C12C—C11C	120.0
C6B—C5B—C4B	120.0	C13C—C12C—H12C	120.0
C6B—C5B—H5B	120.0	C11C—C12C—H12C	120.0
C4B—C5B—H5B	120.0	C12C—C13C—C8C	120.0
C5B—C6B—C7B	120.0	C12C—C13C—H13C	120.0
C5B—C6B—H6B	120.0	C8C—C13C—H13C	120.0
C8A—C1A—N1A—N2A	−123.0 (10)	N2B—C2B—C7B—C6B	179.9 (4)
C1B—C1A—N1A—N2A	113.6 (10)	N1B—C1B—C8B—C9B	−48.4 (4)
C1A—N1A—N2A—C2A	−178.7 (8)	C1A—C1B—C8B—C9B	72.8 (5)
N1A—N2A—C2A—C3A	−174.3 (9)	N1B—C1B—C8B—C13B	128.3 (3)
N1A—N2A—C2A—C7A	1.8 (14)	C1A—C1B—C8B—C13B	−110.5 (4)
C7A—C2A—C3A—C4A	0.0	C13B—C8B—C9B—C10B	0.0
N2A—C2A—C3A—C4A	176.2 (8)	C1B—C8B—C9B—C10B	176.7 (3)
C2A—C3A—C4A—C5A	0.0	C8B—C9B—C10B—C11B	0.0
C3A—C4A—C5A—C6A	0.0	C9B—C10B—C11B—C12B	0.0
C4A—C5A—C6A—C7A	0.0	C9B—C10B—C11B—Cl1B	−179.0 (3)
C5A—C6A—C7A—C2A	0.0	C10B—C11B—C12B—C13B	0.0
C3A—C2A—C7A—C6A	0.0	Cl1B—C11B—C12B—C13B	178.9 (3)
N2A—C2A—C7A—C6A	−175.9 (9)	C11B—C12B—C13B—C8B	0.0
N1A—C1A—C8A—C9A	−56.0 (7)	C9B—C8B—C13B—C12B	0.0
C1B—C1A—C8A—C9A	62.5 (6)	C1B—C8B—C13B—C12B	−176.7 (3)
N1A—C1A—C8A—C13A	125.6 (6)	C8C—C1C—N1C—N2C	−120.6 (16)
C1B—C1A—C8A—C13A	−116.0 (5)	C1C^i—C1C—N1C—N2C	123.4 (17)
C13A—C8A—C9A—C10A	0.0	C1C—N1C—N2C—C2C	174.4 (13)
C1A—C8A—C9A—C10A	−178.5 (6)	N1C—N2C—C2C—C3C	164.3 (14)
C8A—C9A—C10A—C11A	0.0	N1C—N2C—C2C—C7C	−17 (2)
C9A—C10A—C11A—C12A	0.0	C7C—C2C—C3C—C4C	0.0
C9A—C10A—C11A—Cl1A	176.5 (7)	N2C—C2C—C3C—C4C	178.5 (13)
C10A—C11A—C12A—C13A	0.0	C2C—C3C—C4C—C5C	0.0
Cl1A—C11A—C12A—C13A	−176.6 (6)	C3C—C4C—C5C—C6C	0.0
C11A—C12A—C13A—C8A	0.0	C4C—C5C—C6C—C7C	0.0
C9A—C8A—C13A—C12A	0.0	C5C—C6C—C7C—C2C	0.0
C1A—C8A—C13A—C12A	178.5 (6)	C3C—C2C—C7C—C6C	0.0
N1A—C1A—C1B—N1B	−69.1 (6)	N2C—C2C—C7C—C6C	−178.3 (14)
C8A—C1A—C1B—N1B	172.9 (4)	N1C—C1C—C8C—C9C	−56.3 (13)
N1A—C1A—C1B—C8B	169.1 (5)	C1C^i—C1C—C8C—C9C	57.1 (13)
C8A—C1A—C1B—C8B	51.1 (6)	N1C—C1C—C8C—C13C	122.3 (11)
C8B—C1B—N1B—N2B	−121.7 (5)	C1C^i—C1C—C8C—C13C	−124.3 (10)
C1A—C1B—N1B—N2B	112.8 (6)	C13C—C8C—C9C—C10C	0.0
C1B—N1B—N2B—C2B	−179.8 (4)	C1C—C8C—C9C—C10C	178.6 (12)
N1B—N2B—C2B—C3B	−173.1 (4)	C8C—C9C—C10C—C11C	0.0
N1B—N2B—C2B—C7B	7.0 (7)	C9C—C10C—C11C—C12C	0.0
C7B—C2B—C3B—C4B	0.0	C9C—C10C—C11C—Cl1C	−178.4 (11)
N2B—C2B—C3B—C4B	−179.9 (4)	C10C—C11C—C12C—C13C	0.0
C2B—C3B—C4B—C5B	0.0	Cl1C—C11C—C12C—C13C	178.3 (12)
C3B—C4B—C5B—C6B	0.0	C11C—C12C—C13C—C8C	0.0
C4B—C5B—C6B—C7B	0.0	C9C—C8C—C13C—C12C	0.0
C5B—C6B—C7B—C2B	0.0	C1C—C8C—C13C—C12C	−178.6 (11)
C3B—C2B—C7B—C6B	0.0

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