A new pseudopolymorph of hexa­kis(4-cyano­phenyl)benzene

The title compound (systematic name: benzene-4,4′,4′′,4′′′,4′′′′,4′′′′′-­hexayl­hexa­benzo­nitrile dichloro­methane disolvate), C₄₈H₂₄N₆·2CH₂Cl₂, crystallizes as an inclusion compound during the slow diffusion of methanol into a solution of hexa­kis(4-cyano­phenyl)­benzene in CH₂Cl₂. The hexa­kis(4-cyano­phenyl)benzene mol­ecule lies on an axis of twofold rotation in the space group Pbcn. Weak C—H...N inter­actions between hexa­kis(4-cyano­phenyl)benzene mol­ecules define an open network with space for including guests. The resulting structure is a new pseudopolymorph of hexa­kis(4-cyano­phenyl)benzene. The eight known pseudopolymorphs have few shared architectural features, in part because none of the inter­molecular inter­actions that are present plays a dominant role or forces neighboring mol­ecules to assume particular relative orientations.

S1. Comment

Networks of hydrogen bonds continue to be used extensively by crystal engineers to help maintain the integrity of crystals and to position their constituent molecules predictably (Wuest, 2005). Hydrogen bonds offer the advantages of strength and directionality, leading to the formation of robust networks that frequently define cavities or channels for the inclusion of guests. Crystal engineers have also explored the potential of weaker intermolecular interactions, which can exhibit some of the geometric, structural and spectroscopic characteristics of hydrogen bonds (Desiraju, 2002). For example, we recently reported a study of structures maintained in part by weak C—H···N interactions involving the nitrile groups of hexakis(4-cyanophenyl)benzene, (I) (Maly et al., 2006). Despite having a well defined molecular geometry imposed by the hexaphenylbenzene core, compound (I) crystallized under seven different sets of conditions to give inclusion compounds with widely different structures. Although networks maintained by C—H···N interactions were observed in all of these pseudopolymorphs, the particular geometries of the interactions varied widely and the overall structures proved to depend critically on the choice of solvent. These observations underscore the difficulty of using C—H···N interactions to engineer crystals with predictable structural features.

This conclusion has now been reinforced by the analysis of the structure of a new pseudopolymorph obtained by crystallizing compound (I) from CH₃OH–CH₂Cl₂ as the dichloromethane disolvate, (II). In this structure, the molecule of (I) lies on an axis of twofold rotation directed through atoms C1 and C4 in the plane of the inner benzene ring composed of atoms C1–C4/C3ⁱ/C2ⁱ [symmetry code: (i) −x, y, −z + 1/2]. The hexaphenylbenzene core of compound (II) has a chiral propeller conformation, with torsion angles in the range 61.97 (4)–73.37 (4)° (Fig. 1). Similar conformations have been noted in other pseudopolymorphs of compound (I) (Maly et al., 2006).

The observed structure contains equal numbers of each enantiomer. The disc-like shape of hexaphenylbenzene and its derivatives normally favors structures in which the molecules lie parallel and define distinct layers. For example, hexaphenylbenzene itself (Bart, 1968), its inclusion compound with anisole (Larson et al., 1990), and its derivatives substituted in the para position by 4-(carboxyphenyl)ethynyl (Kobayashi et al., 2005), iodo (Kobayashi et al., 2005), –COOH (Kobayashi et al., 2000), trifluorovinyloxy (Spraul et al., 2004), hydroxyl (Kobayashi et al., 1999), ethynyl (Constable et al., 2000), –CONH₂ (Kobayashi et al., 2003) and –CN (Maly et al., 2006), all have crystal structures in which the molecules are roughly coplanar. In contrast, the new polymorph of (I) crystallizes to form a structure in which the molecules occupy two sets of planes, which intersect along the b axis at an angle of 68.29 (3)°. The only previously reported non-coplanar architecture was obtained when hexakis(4-carbamoylphenyl)benzene was crystallized under hydrothermal conditions (Kobayashi et al., 2003).

Each molecule of (I) is surrounded by 14 neighbors, with ten neighbors linked to the central molecule by a total of 12 C—H···N interactions involving H···N distances less than 2.80 Å and C—H···N angles greater than 90° (Fig. 2). Four additional neighbors have C—H···N interactions that are only slightly longer [H···N distances of 2.85 (1) Å] (Fig. 2). The resulting network defines spaces for including partially disordered molecules of CH₂Cl₂, which engage in van der Waals interactions and C—H···N interactions with nearby molecules of compound (I). Specifically, atom Cl1 is in close contact [3.324 (8) Å] with the centroid (Cg1) of the inner benzene ring of the molecule at (x + 1, y, z), with a C29—Cl1···Cg1 angle of 163.6 (3)°. Approximately 21% of the volume of the crystal is accessible to guests, as measured by standard methods (Spek, 2003). This value falls within the wide range of percentages (15–58%) found in the other seven known pseudopolymorphs of (I). It is interesting to note that compound (I) crystallizes from pure CH₃OH as an inclusion compound of composition (I)·2CH₃OH (Maly et al., 2006), whereas crystallization from CH₃OH–CH₂Cl₂ produces an inclusion compound containing only CH₂Cl₂, which is presumably a preferred guest.

Together, these observations confirm that nitrile groups tend to engage in C—H···N interactions and can help direct the construction of open molecular networks. However, the use of these interactions in crystal engineering is limited by their weakness and lack of clear directional preferences, which lead, in the case of (II), to crystallization as multiple pseudopolymorphs with very diverse structures.

S2. Experimental

Hexakis(4-cyanophenyl)benzene, (I), was synthesized by the reported method of Maly et al. (2006). Crystals were grown by placing a solution of compound (I) in CH₂Cl₂ (0.1 M, 2 ml) at the bottom of a test tube, then carefully covering it with successive layers composed of pure CH₂Cl₂ (1 ml), a 1:1 mixture of CH₂Cl₂ and CH₃OH (1 ml), and finally pure CH₃OH (2 ml). The test tube was sealed tightly and left undisturbed. Crystals of (II) appeared after how long?

S3. Refinement

H atoms were placed in idealized positions, with C—H distances in the range 0.95–0.99 Å, and refined using a riding model, with U_iso(H) = 1.2U_eq(C).

The dichloromethane molecule was found to be disordered over two sites. The first molecule (C29, Cl1 and Cl2) was refined with restraints on the C—Cl distances and atomic displacement parameters by the use of SADI and DELU instructions in SHELXL97 (Sheldrick, 1997). The second part of the disordered dichloromethane molecule (C30, Cl3 and Cl4) was refined to be similar to the first one by use of SAME and EADP instructions in SHELXL97. With these restraints, the occupancy factors converged to 0.5312 (11) and 0.4688 (11).

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: enCIFer (Allen et al., 2004) and publCIF (Westrip, 2006).

Figures

	Fig. 1. A view of the structure of (II), with the atom-numbering scheme of the asymmetric unit. Displacement ellipsoids are drawn at the 50% probability level. Only one part of the disordered solvent molecules is shown. The unlabeled parts of the molecules are related by the symmetry operation (−x, y, −z + 1/2).
	Fig. 2. View of a central molecule of (I) (black), showing the neighboring molecules that are linked to it by C—H···N interactions (broken lines) with H···N distances of less than 2.80 Å (dark gray) and H···N distances of 2.85 (1) Å (light gray). H atoms not involved in hydrogen bonding have been omitted for clarity.

4,4',4'',4''',4'''',4'''''-benzenehexaylhexabenzonitrile dichloromethane disolvate

Crystal data

C48H24N6·2CH2Cl2	F(000) = 1752
Mr = 854.58	Dx = 1.311 Mg m^−3
Orthorhombic, Pbcn	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2n 2ab	Cell parameters from 17112 reflections
a = 11.0921 (3) Å	θ = 4.4–67.2°
b = 19.3442 (3) Å	µ = 2.82 mm^−1
c = 20.1742 (4) Å	T = 150 K
V = 4328.73 (16) Å^3	Block, colorless
Z = 4	0.15 × 0.08 × 0.07 mm

Data collection

Bruker SMART 6000 diffractometer	3865 independent reflections
Radiation source: Rotating Anode	3494 reflections with I > 2σ(I)
Montel 200 optics monochromator	Rint = 0.051
Detector resolution: 5.5 pixels mm^-1	θmax = 68.2°, θmin = 4.4°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	k = −23→23
Tmin = 0.700, Tmax = 0.850	l = −23→23
57445 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.119P)^2] where P = (Fo^2 + 2Fc^2)/3
3865 reflections	(Δ/σ)max < 0.001
286 parameters	Δρmax = 0.27 e Å^−3
11 restraints	Δρmin = −0.28 e Å^−3

Special details

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	Occ. (<1)
C1	0.0000	0.54553 (6)	0.2500	0.0295 (3)
N1	0.0000	0.88565 (7)	0.2500	0.0705 (5)
C2	0.06316 (8)	0.51073 (5)	0.19855 (4)	0.0289 (2)
N2	0.37714 (12)	0.67215 (6)	−0.05659 (6)	0.0651 (4)
C3	0.06362 (8)	0.44098 (5)	0.19866 (5)	0.0307 (2)
N3	0.38402 (16)	0.26434 (11)	−0.04262 (11)	0.1071 (7)
C4	0.0000	0.40677 (7)	0.2500	0.0312 (3)
N4	0.0000	0.06745 (7)	0.2500	0.0586 (4)
C5	0.0000	0.61995 (6)	0.2500	0.0309 (3)
C6	−0.05247 (10)	0.65481 (5)	0.19553 (5)	0.0372 (3)
H6	−0.0871	0.6296	0.1599	0.045*
C7	−0.05239 (11)	0.72363 (5)	0.19524 (6)	0.0434 (3)
H7	−0.0864	0.7489	0.1594	0.052*
C8	0.0000	0.75784 (7)	0.2500	0.0431 (4)
C9	0.0000	0.82943 (8)	0.2500	0.0509 (4)
C10	0.12990 (9)	0.54787 (5)	0.14348 (5)	0.0316 (2)
C11	0.23002 (10)	0.58647 (5)	0.15963 (5)	0.0398 (3)
H11	0.2560	0.5903	0.2044	0.048*
C12	0.29244 (11)	0.61985 (6)	0.10888 (6)	0.0454 (3)
H12	0.3608	0.6471	0.1200	0.054*
C13	0.25731 (10)	0.61477 (5)	0.03955 (6)	0.0412 (3)
C14	0.15595 (11)	0.57602 (6)	0.02361 (5)	0.0424 (3)
H14	0.1298	0.5720	−0.0211	0.051*
C15	0.09324 (10)	0.54306 (6)	0.07492 (5)	0.0390 (3)
H15	0.0239	0.5165	0.0642	0.047*
C16	0.32203 (12)	0.64664 (6)	−0.01203 (6)	0.0493 (3)
C17	0.13343 (9)	0.40327 (5)	0.14529 (5)	0.0333 (2)
C18	0.25865 (10)	0.40777 (5)	0.14290 (6)	0.0396 (3)
H18	0.3001	0.4358	0.1742	0.048*
C19	0.32396 (10)	0.37149 (6)	0.09494 (6)	0.0495 (3)
H19	0.4094	0.3746	0.0942	0.059*
C20	0.26421 (12)	0.33033 (7)	0.04765 (7)	0.0535 (3)
C21	0.13814 (12)	0.32596 (6)	0.05053 (6)	0.0493 (3)
H21	0.0961	0.2986	0.0190	0.059*
C22	0.07419 (10)	0.36141 (5)	0.09914 (6)	0.0392 (3)
H22	−0.0111	0.3571	0.1010	0.047*
C23	0.32914 (15)	0.29406 (8)	−0.00100 (9)	0.0743 (5)
C24	0.0000	0.33275 (7)	0.2500	0.0334 (3)
C25	−0.10428 (10)	0.29803 (5)	0.23224 (6)	0.0409 (3)
H25	−0.1750	0.3230	0.2207	0.049*
C26	−0.10419 (10)	0.22943 (5)	0.23159 (7)	0.0446 (3)
H26	−0.1741	0.2044	0.2188	0.054*
C27	0.0000	0.19525 (7)	0.2500	0.0403 (4)
C28	0.0000	0.12432 (8)	0.2500	0.0442 (4)
C29	0.6145 (6)	0.4921 (2)	0.1182 (4)	0.0666 (7)	0.5312 (11)
H29A	0.6001	0.4598	0.0810	0.080*	0.5312 (11)
H29B	0.5464	0.4881	0.1497	0.080*	0.5312 (11)
Cl1	0.7509 (7)	0.4705 (3)	0.1586 (4)	0.0848 (8)	0.5312 (11)
Cl2	0.62378 (12)	0.57770 (7)	0.08797 (6)	0.1118 (3)	0.5312 (11)
C30	0.6042 (7)	0.4850 (4)	0.1294 (3)	0.0666 (7)	0.4688 (11)
H30A	0.5789	0.4362	0.1252	0.080*	0.4688 (11)
H30B	0.5519	0.5076	0.1627	0.080*	0.4688 (11)
Cl3	0.7561 (8)	0.4891 (3)	0.1554 (5)	0.0848 (8)	0.4688 (11)
Cl4	0.58793 (15)	0.52710 (7)	0.05219 (7)	0.1118 (3)	0.4688 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0315 (7)	0.0264 (6)	0.0306 (7)	0.000	−0.0028 (5)	0.000
N1	0.0845 (12)	0.0302 (7)	0.0967 (14)	0.000	0.0255 (10)	0.000
C2	0.0324 (5)	0.0258 (4)	0.0285 (5)	−0.0015 (3)	−0.0026 (4)	0.0002 (3)
N2	0.0811 (8)	0.0476 (6)	0.0668 (8)	−0.0113 (6)	0.0285 (6)	0.0048 (5)
C3	0.0307 (5)	0.0276 (5)	0.0337 (6)	−0.0004 (3)	−0.0019 (4)	−0.0026 (3)
N3	0.0891 (11)	0.1170 (13)	0.1150 (16)	0.0123 (10)	0.0248 (10)	−0.0638 (12)
C4	0.0292 (6)	0.0277 (6)	0.0367 (7)	0.000	−0.0035 (5)	0.000
N4	0.0661 (10)	0.0337 (7)	0.0759 (11)	0.000	0.0046 (8)	0.000
C5	0.0355 (7)	0.0261 (6)	0.0312 (7)	0.000	0.0039 (5)	0.000
C6	0.0448 (6)	0.0317 (5)	0.0350 (6)	0.0020 (4)	0.0007 (4)	0.0013 (4)
C7	0.0516 (7)	0.0333 (5)	0.0452 (7)	0.0046 (4)	0.0049 (5)	0.0095 (4)
C8	0.0500 (9)	0.0251 (6)	0.0542 (10)	0.000	0.0171 (7)	0.000
C9	0.0579 (10)	0.0328 (8)	0.0622 (11)	0.000	0.0231 (8)	0.000
C10	0.0352 (5)	0.0270 (4)	0.0325 (5)	−0.0007 (4)	0.0010 (4)	−0.0017 (3)
C11	0.0429 (6)	0.0440 (5)	0.0327 (6)	−0.0096 (4)	−0.0015 (4)	−0.0022 (4)
C12	0.0448 (6)	0.0435 (6)	0.0478 (7)	−0.0139 (5)	0.0036 (5)	−0.0046 (5)
C13	0.0459 (6)	0.0329 (5)	0.0447 (7)	0.0001 (4)	0.0097 (4)	0.0019 (4)
C14	0.0522 (6)	0.0426 (5)	0.0324 (6)	−0.0061 (5)	−0.0017 (5)	0.0023 (4)
C15	0.0431 (6)	0.0396 (5)	0.0343 (6)	−0.0079 (4)	−0.0021 (4)	−0.0014 (4)
C16	0.0571 (7)	0.0374 (5)	0.0534 (7)	−0.0044 (5)	0.0115 (6)	−0.0018 (5)
C17	0.0369 (5)	0.0283 (4)	0.0348 (5)	0.0020 (4)	0.0007 (4)	−0.0010 (4)
C18	0.0393 (6)	0.0365 (5)	0.0429 (6)	−0.0002 (4)	0.0030 (4)	−0.0068 (4)
C19	0.0388 (6)	0.0522 (6)	0.0575 (8)	0.0003 (5)	0.0090 (5)	−0.0120 (5)
C20	0.0547 (7)	0.0478 (6)	0.0581 (8)	0.0035 (5)	0.0100 (6)	−0.0177 (5)
C21	0.0550 (7)	0.0431 (6)	0.0499 (7)	0.0013 (5)	−0.0027 (5)	−0.0170 (5)
C22	0.0415 (5)	0.0318 (5)	0.0442 (6)	−0.0002 (4)	−0.0017 (4)	−0.0059 (4)
C23	0.0641 (9)	0.0734 (9)	0.0855 (11)	0.0025 (7)	0.0102 (8)	−0.0363 (9)
C24	0.0360 (7)	0.0294 (7)	0.0347 (7)	0.000	0.0024 (6)	0.000
C25	0.0395 (6)	0.0298 (5)	0.0534 (7)	−0.0013 (4)	−0.0027 (5)	0.0039 (4)
C26	0.0442 (6)	0.0322 (5)	0.0574 (8)	−0.0083 (4)	−0.0030 (5)	0.0005 (4)
C27	0.0493 (9)	0.0277 (6)	0.0438 (8)	0.000	0.0076 (6)	0.000
C28	0.0472 (9)	0.0334 (8)	0.0522 (10)	0.000	0.0086 (7)	0.000
C29	0.0634 (13)	0.0775 (13)	0.0591 (19)	0.0014 (10)	0.0024 (14)	−0.0105 (9)
Cl1	0.0630 (6)	0.120 (3)	0.0714 (8)	−0.0069 (16)	−0.0152 (5)	−0.0179 (17)
Cl2	0.1311 (7)	0.1109 (6)	0.0935 (6)	0.0271 (5)	0.0168 (5)	0.0294 (4)
C30	0.0634 (13)	0.0775 (13)	0.0591 (19)	0.0014 (10)	0.0024 (14)	−0.0105 (9)
Cl3	0.0630 (6)	0.120 (3)	0.0714 (8)	−0.0069 (16)	−0.0152 (5)	−0.0179 (17)
Cl4	0.1311 (7)	0.1109 (6)	0.0935 (6)	0.0271 (5)	0.0168 (5)	0.0294 (4)

Geometric parameters (Å, º)

C1—C2^i	1.4217 (11)	C14—H14	0.9500
C1—C2	1.4217 (11)	C15—H15	0.9500
C1—C5	1.4397 (17)	C17—C18	1.3925 (15)
N1—C9	1.088 (2)	C17—C22	1.3980 (14)
C2—C3	1.3493 (13)	C18—C19	1.3977 (15)
C2—C10	1.5161 (13)	C18—H18	0.9500
N2—C16	1.1939 (17)	C19—C20	1.4083 (18)
C3—C4	1.4173 (11)	C19—H19	0.9500
C3—C17	1.5136 (13)	C20—C21	1.4021 (19)
N3—C23	1.186 (2)	C20—C23	1.4051 (19)
C4—C3^i	1.4173 (11)	C21—C22	1.3910 (16)
C4—C24	1.4318 (18)	C21—H21	0.9500
N4—C28	1.100 (2)	C22—H22	0.9500
C5—C6^i	1.4144 (12)	C24—C25^i	1.3847 (12)
C5—C6	1.4145 (12)	C24—C25	1.3848 (12)
C6—C7	1.3314 (14)	C25—C26	1.3271 (14)
C6—H6	0.9500	C25—H25	0.9500
C7—C8	1.4128 (14)	C26—C27	1.3823 (13)
C7—H7	0.9500	C26—H26	0.9500
C8—C9	1.385 (2)	C27—C28	1.3721 (19)
C8—C7^i	1.4128 (14)	C27—C26^i	1.3824 (14)
C10—C11	1.3773 (15)	C29—Cl2	1.768 (3)
C10—C15	1.4447 (15)	C29—Cl1	1.768 (2)
C11—C12	1.3945 (16)	C29—H29A	0.9900
C11—H11	0.9500	C29—H29B	0.9900
C12—C13	1.4553 (18)	C30—Cl4	1.766 (3)
C12—H12	0.9500	C30—Cl3	1.767 (3)
C13—C14	1.3891 (16)	C30—H30A	0.9900
C13—C16	1.4065 (17)	C30—H30B	0.9900
C14—C15	1.4007 (16)
C2^i—C1—C2	123.49 (11)	C18—C17—C22	118.81 (10)
C2^i—C1—C5	118.25 (6)	C18—C17—C3	120.32 (9)
C2—C1—C5	118.26 (6)	C22—C17—C3	120.83 (9)
C3—C2—C1	118.30 (8)	C17—C18—C19	120.64 (10)
C3—C2—C10	118.24 (8)	C17—C18—H18	119.7
C1—C2—C10	123.46 (8)	C19—C18—H18	119.7
C2—C3—C4	117.79 (9)	C18—C19—C20	120.59 (11)
C2—C3—C17	118.87 (8)	C18—C19—H19	119.7
C4—C3—C17	123.33 (8)	C20—C19—H19	119.7
C3^i—C4—C3	124.32 (12)	C21—C20—C23	120.66 (13)
C3^i—C4—C24	117.84 (6)	C21—C20—C19	118.39 (11)
C3—C4—C24	117.84 (6)	C23—C20—C19	120.95 (12)
C6^i—C5—C6	123.06 (12)	C22—C21—C20	120.53 (11)
C6^i—C5—C1	118.47 (6)	C22—C21—H21	119.7
C6—C5—C1	118.47 (6)	C20—C21—H21	119.7
C7—C6—C5	118.67 (10)	C21—C22—C17	121.03 (10)
C7—C6—H6	120.7	C21—C22—H22	119.5
C5—C6—H6	120.7	C17—C22—H22	119.5
C6—C7—C8	117.73 (10)	N3—C23—C20	179.0 (2)
C6—C7—H7	121.1	C25^i—C24—C25	121.97 (13)
C8—C7—H7	121.1	C25^i—C24—C4	119.02 (6)
C9—C8—C7^i	117.94 (6)	C25—C24—C4	119.02 (6)
C9—C8—C7	117.93 (6)	C26—C25—C24	119.14 (10)
C7^i—C8—C7	124.13 (13)	C26—C25—H25	120.4
N1—C9—C8	180.000 (1)	C24—C25—H25	120.4
C11—C10—C15	119.24 (9)	C25—C26—C27	118.44 (10)
C11—C10—C2	118.50 (9)	C25—C26—H26	120.8
C15—C10—C2	122.25 (8)	C27—C26—H26	120.8
C10—C11—C12	118.53 (10)	C28—C27—C26	118.57 (7)
C10—C11—H11	120.7	C28—C27—C26^i	118.57 (7)
C12—C11—H11	120.7	C26—C27—C26^i	122.86 (13)
C11—C12—C13	122.78 (10)	N4—C28—C27	180.0
C11—C12—H12	118.6	Cl2—C29—Cl1	109.3 (3)
C13—C12—H12	118.6	Cl2—C29—H29A	109.8
C14—C13—C16	118.58 (11)	Cl1—C29—H29A	109.8
C14—C13—C12	118.41 (10)	Cl2—C29—H29B	109.8
C16—C13—C12	123.01 (10)	Cl1—C29—H29B	109.8
C13—C14—C15	118.45 (10)	H29A—C29—H29B	108.3
C13—C14—H14	120.8	Cl4—C30—Cl3	109.8 (4)
C15—C14—H14	120.8	Cl4—C30—H30A	109.7
C14—C15—C10	122.58 (10)	Cl3—C30—H30A	109.7
C14—C15—H15	118.7	Cl4—C30—H30B	109.7
C10—C15—H15	118.7	Cl3—C30—H30B	109.7
N2—C16—C13	178.37 (12)	H30A—C30—H30B	108.2

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···N2^ii	0.95	2.65	3.5076 (17)	151
C7—H7···N2^iii	0.95	2.61	3.5355 (16)	165
C21—H21···N3^iv	0.95	2.69	3.320 (2)	124
C29—H29B···N4^v	0.99	2.59	3.288 (9)	127

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