2-{2,4,6-Tris(bromo-meth-yl)-3,5-bis-[(1,3-dioxoisoindolin-2-yl)meth-yl]benz-yl}iso-indoline-1,3-dione toluene monosolvate.

In the title compound, C36H24Br3N3O6·C7H8, the toluene solvent mol-ecule is associated with the receptor mol-ecule via C-H⋯π bonding. The planes of the phthalimido groups are inclined at 77.0 (1), 63.0 (1) and 77.8 (1)° with respect to the benzene ring. The mol-ecular conformation is stabilized by C-H⋯O and C-H⋯Br hydrogen bonds. The crystal structure features non-classical hydrogen bonds of the C-H⋯N, C-H⋯O and C-H⋯Br type, leading to a three-dimensional cross-linking of molecules. The pattern of non-covalent inter-molecular bonding is completed by O⋯Br halogen bonds [3.306 (3) Å], which link the receptor mol-ecules into infinite strands extending along the a-axis direction.

Related literature

For heteroditopic receptors and their applications, see: McConnell & Beer (2012 ▶); Kirkovits et al. (2001 ▶); Kinnear et al. (1994 ▶); Hossain & Schneider (1998 ▶); Tsukube et al. (1999 ▶); Smith (2010 ▶). For C—H⋯π inter­actions, see: Nishio et al. (2009 ▶). For non-classic hydrogen bonds, see: Desiraju & Steiner (1999 ▶). For halogen bonding, see: Metrangolo & Resnati (2008 ▶). For the synthesis and use of the title compound, see: Roelens et al. (2009 ▶).

Experimental

Crystal data

C36H24Br3N3O6·C7H8

M = 926.45

Orthorhombic,

a = 9.2879 (2) Å

b = 39.2730 (11) Å

c = 10.5592 (3) Å

V = 3851.61 (17) Å3

Z = 4

Mo Kα radiation

μ = 3.20 mm−1

T = 100 K

0.50 × 0.42 × 0.34 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.298, T max = 0.410

59694 measured reflections

10997 independent reflections

10267 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.057

S = 1.06

10997 reflections

482 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.43 e Å−3

Absolute structure: Flack (1983 ▶), 5205 Friedel pairs

Absolute structure parameter: 0.015 (4)

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814004383/xu5768sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814004383/xu5768Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814004383/xu5768Isup3.cml

CCDC reference: 988768

Additional supporting information: crystallographic information; 3D view; checkCIF report

C36H24Br3N3O6·C7H8	F(000) = 1856
Mr = 926.45	Dx = 1.598 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 9504 reflections
a = 9.2879 (2) Å	θ = 2.6–30.1°
b = 39.2730 (11) Å	µ = 3.20 mm−1
c = 10.5592 (3) Å	T = 100 K
V = 3851.61 (17) Å3	Irregular, colourless
Z = 4	0.50 × 0.42 × 0.34 mm

Bruker APEXII CCD area-detector diffractometer	10997 independent reflections
Radiation source: fine-focus sealed tube	10267 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
phi and ω scans	θmax = 29.8°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→12
Tmin = 0.298, Tmax = 0.410	k = −54→54
59694 measured reflections	l = −14→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026	H-atom parameters constrained
wR(F2) = 0.057	w = 1/[σ2(Fo2) + (0.0167P)2 + 1.9141P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
10997 reflections	Δρmax = 0.41 e Å−3
482 parameters	Δρmin = −0.43 e Å−3
1 restraint	Absolute structure: Flack (1983), 5205 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.015 (4)

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.

	x	y	z	Uiso*/Ueq
Br1	0.87579 (2)	0.101954 (5)	−0.01024 (2)	0.02056 (5)
Br2	1.31949 (2)	0.203008 (5)	0.23399 (2)	0.01976 (4)
Br3	0.62645 (2)	0.184625 (6)	0.55424 (2)	0.02518 (5)
O1	0.62966 (17)	0.18819 (4)	0.09052 (18)	0.0237 (4)
O2	0.50556 (16)	0.07721 (3)	0.15611 (16)	0.0186 (3)
O3	1.16142 (18)	0.04624 (4)	0.10085 (18)	0.0278 (4)
O4	1.3171 (2)	0.10168 (4)	0.45440 (17)	0.0289 (4)
O5	1.10398 (16)	0.16994 (4)	0.62809 (16)	0.0188 (3)
O6	0.81813 (16)	0.26402 (4)	0.58804 (16)	0.0197 (3)
N1	0.58624 (17)	0.13273 (4)	0.15120 (17)	0.0138 (3)
N2	1.20917 (17)	0.08138 (4)	0.27224 (17)	0.0144 (3)
N3	0.97292 (17)	0.21791 (4)	0.57551 (16)	0.0123 (3)
C1	0.79776 (19)	0.14557 (5)	0.29093 (19)	0.0118 (4)
C2	0.90990 (19)	0.12503 (4)	0.2461 (2)	0.0120 (3)
C3	1.0543 (2)	0.13449 (5)	0.26749 (18)	0.0117 (4)
C4	1.0854 (2)	0.16428 (5)	0.33462 (19)	0.0113 (4)
C5	0.9733 (2)	0.18575 (4)	0.37434 (19)	0.0109 (4)
C6	0.8299 (2)	0.17643 (5)	0.35213 (19)	0.0120 (4)
C7	0.8773 (2)	0.09313 (5)	0.1739 (2)	0.0146 (4)
H7A	0.7823	0.0842	0.2003	0.017*
H7B	0.9508	0.0757	0.1935	0.017*
C8	1.2373 (2)	0.17347 (5)	0.3659 (2)	0.0132 (4)
H8A	1.2957	0.1525	0.3733	0.016*
H8B	1.2401	0.1854	0.4484	0.016*
C9	0.7111 (2)	0.19981 (5)	0.3924 (2)	0.0164 (4)
H9A	0.6356	0.2003	0.3263	0.020*
H9B	0.7494	0.2232	0.4021	0.020*
C10	0.6420 (2)	0.13404 (5)	0.2795 (2)	0.0144 (4)
H10A	0.6332	0.1111	0.3176	0.017*
H10B	0.5810	0.1497	0.3297	0.017*
C11	0.5808 (2)	0.16045 (5)	0.0676 (2)	0.0181 (4)
C12	0.5030 (2)	0.14809 (6)	−0.0454 (2)	0.0193 (4)
C13	0.4667 (2)	0.16503 (7)	−0.1558 (2)	0.0302 (6)
H13	0.4953	0.1879	−0.1703	0.036*
C14	0.3862 (2)	0.14693 (9)	−0.2448 (3)	0.0396 (7)
H14	0.3603	0.1577	−0.3221	0.048*
C15	0.3432 (3)	0.11369 (9)	−0.2229 (3)	0.0413 (8)
H15	0.2870	0.1022	−0.2848	0.050*
C16	0.3809 (2)	0.09660 (8)	−0.1111 (3)	0.0302 (6)
H16	0.3523	0.0738	−0.0957	0.036*
C17	0.4624 (2)	0.11481 (6)	−0.0243 (2)	0.0196 (4)
C18	0.5164 (2)	0.10438 (5)	0.1015 (2)	0.0151 (4)
C19	1.1748 (2)	0.11348 (5)	0.20873 (19)	0.0132 (4)
H19A	1.1484	0.1084	0.1199	0.016*
H19B	1.2630	0.1276	0.2067	0.016*
C20	1.2076 (2)	0.05012 (5)	0.2068 (2)	0.0194 (5)
C21	1.2715 (2)	0.02478 (5)	0.2940 (2)	0.0220 (5)
C22	1.2896 (2)	−0.01012 (6)	0.2806 (3)	0.0313 (6)
H22	1.2603	−0.0217	0.2059	0.038*
C23	1.3520 (3)	−0.02728 (6)	0.3804 (4)	0.0386 (7)
H23	1.3643	−0.0512	0.3749	0.046*
C24	1.3972 (3)	−0.01038 (6)	0.4888 (4)	0.0392 (7)
H24	1.4407	−0.0229	0.5555	0.047*
C25	1.3799 (3)	0.02466 (6)	0.5013 (3)	0.0327 (6)
H25	1.4109	0.0364	0.5751	0.039*
C26	1.3160 (2)	0.04157 (5)	0.4020 (2)	0.0223 (5)
C27	1.2844 (2)	0.07837 (5)	0.3867 (2)	0.0191 (4)
C28	1.0073 (2)	0.21895 (5)	0.44127 (19)	0.0124 (4)
H28A	1.1110	0.2241	0.4309	0.015*
H28B	0.9520	0.2376	0.4009	0.015*
C29	1.0301 (2)	0.19385 (5)	0.6595 (2)	0.0148 (4)
C30	0.9806 (2)	0.20383 (5)	0.7871 (2)	0.0170 (4)
C31	1.0109 (2)	0.18917 (6)	0.9036 (2)	0.0217 (5)
H31	1.0716	0.1698	0.9110	0.026*
C32	0.9476 (3)	0.20435 (6)	1.0092 (2)	0.0292 (5)
H32	0.9658	0.1953	1.0911	0.035*
C33	0.8587 (3)	0.23229 (6)	0.9963 (3)	0.0299 (5)
H33	0.8164	0.2419	1.0701	0.036*
C34	0.8289 (3)	0.24692 (6)	0.8796 (2)	0.0232 (5)
H34	0.7676	0.2662	0.8721	0.028*
C35	0.8927 (2)	0.23217 (5)	0.7747 (2)	0.0172 (4)
C36	0.8850 (2)	0.24137 (5)	0.6388 (2)	0.0155 (4)
C1A	0.8364 (2)	0.03354 (5)	0.44059 (17)	0.0507 (9)
C2A	0.7319 (2)	0.05829 (5)	0.4604 (2)	0.0498 (8)
H2A	0.6435	0.0573	0.4151	0.060*
C3A	0.7565 (3)	0.08446 (5)	0.5463 (2)	0.0810 (14)
H3A	0.6850	0.1014	0.5598	0.097*
C4A	0.8858 (4)	0.08588 (6)	0.6124 (2)	0.0887 (18)
H4A	0.9026	0.1038	0.6712	0.106*
C5A	0.9904 (3)	0.06113 (8)	0.5927 (2)	0.0813 (15)
H5A	1.0787	0.0621	0.6379	0.098*
C6A	0.96570 (19)	0.03496 (7)	0.5067 (2)	0.0693 (12)
H6A	1.0372	0.0180	0.4932	0.083*
C7A	0.8255 (4)	0.00470 (6)	0.3449 (2)	0.0941 (18)
H7A1	0.7240	−0.0012	0.3319	0.141*
H7A2	0.8776	−0.0152	0.3767	0.141*
H7A3	0.8677	0.0120	0.2642	0.141*

	U11	U22	U33	U12	U13	U23
Br1	0.02090 (10)	0.02545 (10)	0.01532 (10)	−0.00046 (8)	−0.00065 (9)	−0.00518 (9)
Br2	0.01633 (8)	0.02241 (9)	0.02055 (10)	−0.00556 (8)	0.00482 (9)	0.00259 (9)
Br3	0.01890 (10)	0.03088 (11)	0.02576 (12)	−0.00392 (8)	0.01001 (10)	−0.01086 (10)
O1	0.0196 (7)	0.0195 (7)	0.0320 (10)	0.0003 (6)	0.0050 (7)	0.0052 (7)
O2	0.0196 (7)	0.0134 (6)	0.0228 (8)	−0.0023 (5)	0.0005 (6)	−0.0051 (6)
O3	0.0283 (9)	0.0211 (8)	0.0340 (10)	0.0060 (6)	−0.0097 (7)	−0.0118 (7)
O4	0.0437 (11)	0.0207 (8)	0.0223 (9)	0.0049 (7)	−0.0119 (7)	−0.0006 (7)
O5	0.0186 (7)	0.0170 (7)	0.0208 (8)	0.0065 (5)	0.0003 (6)	0.0032 (6)
O6	0.0195 (7)	0.0140 (7)	0.0255 (9)	0.0049 (5)	−0.0014 (6)	−0.0022 (6)
N1	0.0108 (8)	0.0153 (7)	0.0152 (9)	−0.0007 (6)	−0.0010 (6)	−0.0015 (6)
N2	0.0132 (8)	0.0125 (7)	0.0176 (9)	0.0024 (6)	0.0003 (6)	−0.0013 (6)
N3	0.0141 (7)	0.0108 (7)	0.0120 (9)	0.0015 (6)	−0.0002 (6)	−0.0023 (6)
C1	0.0089 (8)	0.0136 (8)	0.0130 (10)	−0.0002 (6)	−0.0009 (7)	0.0008 (7)
C2	0.0125 (8)	0.0120 (8)	0.0114 (9)	−0.0012 (6)	0.0001 (7)	0.0007 (7)
C3	0.0121 (8)	0.0107 (8)	0.0122 (9)	0.0024 (6)	−0.0002 (7)	0.0019 (7)
C4	0.0099 (8)	0.0124 (8)	0.0116 (10)	0.0004 (6)	−0.0004 (7)	0.0025 (7)
C5	0.0103 (8)	0.0105 (8)	0.0119 (10)	−0.0008 (6)	−0.0003 (7)	0.0011 (7)
C6	0.0105 (8)	0.0134 (8)	0.0121 (9)	0.0014 (6)	−0.0008 (7)	−0.0012 (7)
C7	0.0154 (9)	0.0129 (8)	0.0153 (10)	−0.0006 (7)	−0.0003 (8)	−0.0021 (7)
C8	0.0110 (8)	0.0133 (8)	0.0153 (10)	−0.0033 (7)	0.0005 (7)	0.0013 (7)
C9	0.0114 (9)	0.0165 (9)	0.0211 (11)	0.0014 (7)	−0.0001 (8)	−0.0059 (8)
C10	0.0100 (8)	0.0182 (9)	0.0148 (10)	−0.0022 (7)	−0.0003 (7)	−0.0027 (7)
C11	0.0116 (8)	0.0216 (9)	0.0211 (11)	0.0037 (7)	0.0046 (8)	0.0024 (9)
C12	0.0113 (9)	0.0303 (11)	0.0163 (11)	0.0051 (8)	0.0026 (7)	0.0028 (8)
C13	0.0156 (10)	0.0522 (15)	0.0228 (13)	0.0093 (10)	0.0039 (9)	0.0130 (11)
C14	0.0174 (11)	0.082 (2)	0.0198 (13)	0.0076 (12)	−0.0012 (10)	0.0112 (13)
C15	0.0153 (11)	0.089 (2)	0.0190 (13)	−0.0030 (12)	−0.0040 (9)	−0.0087 (14)
C16	0.0153 (11)	0.0512 (15)	0.0242 (13)	−0.0040 (10)	−0.0011 (9)	−0.0113 (11)
C17	0.0124 (9)	0.0274 (10)	0.0189 (11)	0.0051 (7)	−0.0001 (8)	−0.0066 (9)
C18	0.0091 (8)	0.0188 (9)	0.0176 (10)	0.0018 (7)	0.0017 (7)	−0.0067 (8)
C19	0.0122 (8)	0.0132 (8)	0.0142 (11)	0.0009 (7)	0.0015 (7)	−0.0003 (7)
C20	0.0141 (9)	0.0149 (9)	0.0291 (14)	0.0011 (7)	0.0005 (8)	−0.0034 (8)
C21	0.0149 (9)	0.0156 (9)	0.0354 (14)	0.0010 (7)	0.0021 (9)	0.0019 (9)
C22	0.0228 (11)	0.0169 (10)	0.0542 (18)	0.0028 (8)	−0.0008 (11)	0.0001 (10)
C23	0.0284 (13)	0.0144 (10)	0.073 (2)	0.0023 (9)	−0.0004 (13)	0.0116 (12)
C24	0.0355 (14)	0.0264 (12)	0.0558 (19)	0.0055 (10)	−0.0055 (14)	0.0185 (14)
C25	0.0336 (13)	0.0279 (11)	0.0366 (15)	0.0050 (10)	0.0006 (12)	0.0129 (11)
C26	0.0188 (10)	0.0174 (9)	0.0306 (13)	0.0021 (8)	0.0019 (9)	0.0067 (9)
C27	0.0195 (10)	0.0190 (9)	0.0189 (11)	0.0036 (8)	−0.0002 (8)	0.0018 (8)
C28	0.0123 (9)	0.0120 (8)	0.0128 (9)	−0.0003 (7)	−0.0016 (7)	0.0002 (7)
C29	0.0119 (9)	0.0169 (9)	0.0157 (10)	−0.0012 (7)	−0.0012 (8)	0.0018 (8)
C30	0.0155 (9)	0.0205 (10)	0.0150 (10)	−0.0058 (8)	−0.0004 (8)	−0.0003 (8)
C31	0.0207 (11)	0.0261 (11)	0.0184 (11)	−0.0059 (8)	−0.0015 (9)	0.0039 (9)
C32	0.0363 (14)	0.0348 (13)	0.0164 (12)	−0.0132 (10)	0.0043 (10)	−0.0003 (9)
C33	0.0392 (14)	0.0307 (11)	0.0197 (12)	−0.0137 (10)	0.0120 (11)	−0.0092 (11)
C34	0.0257 (11)	0.0197 (10)	0.0241 (13)	−0.0056 (8)	0.0079 (10)	−0.0081 (9)
C35	0.0161 (9)	0.0172 (9)	0.0182 (11)	−0.0049 (7)	0.0005 (8)	−0.0051 (8)
C36	0.0127 (9)	0.0134 (8)	0.0202 (11)	−0.0013 (7)	−0.0001 (8)	−0.0048 (8)
C1A	0.055 (2)	0.059 (2)	0.0382 (19)	−0.0185 (16)	0.0039 (15)	0.0224 (16)
C2A	0.057 (2)	0.0499 (18)	0.042 (2)	−0.0087 (15)	−0.0076 (15)	0.0249 (15)
C3A	0.150 (5)	0.045 (2)	0.048 (2)	0.016 (2)	0.005 (3)	0.0289 (19)
C4A	0.180 (6)	0.055 (2)	0.032 (2)	−0.052 (3)	−0.004 (3)	0.0074 (18)
C5A	0.077 (3)	0.096 (3)	0.071 (3)	−0.053 (3)	−0.007 (2)	0.020 (3)
C6A	0.0417 (19)	0.109 (3)	0.057 (3)	−0.019 (2)	0.0108 (17)	0.028 (2)
C7A	0.171 (6)	0.058 (2)	0.053 (3)	−0.017 (3)	0.016 (3)	0.011 (2)

Br1—C7	1.975 (2)	C16—C17	1.387 (3)
Br2—C8	1.967 (2)	C16—H16	0.9500
Br3—C9	1.974 (2)	C17—C18	1.478 (3)
O1—C11	1.205 (3)	C19—H19A	0.9900
O2—C18	1.217 (3)	C19—H19B	0.9900
O3—C20	1.208 (3)	C20—C21	1.480 (3)
O4—C27	1.201 (3)	C21—C26	1.380 (3)
O5—C29	1.209 (2)	C21—C22	1.388 (3)
O6—C36	1.210 (2)	C22—C23	1.379 (4)
N1—C18	1.391 (2)	C22—H22	0.9500
N1—C11	1.403 (3)	C23—C24	1.388 (5)
N1—C10	1.451 (3)	C23—H23	0.9500
N2—C27	1.401 (3)	C24—C25	1.392 (4)
N2—C20	1.409 (3)	C24—H24	0.9500
N2—C19	1.463 (2)	C25—C26	1.376 (4)
N3—C36	1.401 (2)	C25—H25	0.9500
N3—C29	1.401 (3)	C26—C27	1.484 (3)
N3—C28	1.454 (3)	C28—H28A	0.9900
C1—C2	1.400 (3)	C28—H28B	0.9900
C1—C6	1.405 (3)	C29—C30	1.477 (3)
C1—C10	1.521 (3)	C30—C35	1.387 (3)
C2—C3	1.410 (2)	C30—C31	1.387 (3)
C2—C7	1.498 (3)	C31—C32	1.395 (4)
C3—C4	1.398 (3)	C31—H31	0.9500
C3—C19	1.523 (3)	C32—C33	1.380 (4)
C4—C5	1.404 (3)	C32—H32	0.9500
C4—C8	1.494 (3)	C33—C34	1.388 (4)
C5—C6	1.401 (3)	C33—H33	0.9500
C5—C28	1.517 (3)	C34—C35	1.383 (3)
C6—C9	1.496 (3)	C34—H34	0.9500
C7—H7A	0.9900	C35—C36	1.482 (3)
C7—H7B	0.9900	C1A—C2A	1.3900
C8—H8A	0.9900	C1A—C6A	1.3900
C8—H8B	0.9900	C1A—C7A	1.5213
C9—H9A	0.9900	C2A—C3A	1.3900
C9—H9B	0.9900	C2A—H2A	0.9500
C10—H10A	0.9900	C3A—C4A	1.3900
C10—H10B	0.9900	C3A—H3A	0.9500
C11—C12	1.476 (3)	C4A—C5A	1.3900
C12—C17	1.378 (3)	C4A—H4A	0.9500
C12—C13	1.384 (3)	C5A—C6A	1.3900
C13—C14	1.396 (4)	C5A—H5A	0.9500
C13—H13	0.9500	C6A—H6A	0.9500
C14—C15	1.385 (5)	C7A—H7A1	0.9800
C14—H14	0.9500	C7A—H7A2	0.9800
C15—C16	1.402 (4)	C7A—H7A3	0.9800
C15—H15	0.9500
C18—N1—C11	111.52 (18)	H19A—C19—H19B	107.4
C18—N1—C10	123.14 (17)	O3—C20—N2	124.61 (19)
C11—N1—C10	124.97 (17)	O3—C20—C21	129.3 (2)
C27—N2—C20	110.78 (17)	N2—C20—C21	106.06 (19)
C27—N2—C19	125.23 (16)	C26—C21—C22	121.3 (2)
C20—N2—C19	121.58 (17)	C26—C21—C20	108.21 (18)
C36—N3—C29	111.29 (17)	C22—C21—C20	130.5 (2)
C36—N3—C28	125.06 (17)	C23—C22—C21	117.1 (3)
C29—N3—C28	123.58 (16)	C23—C22—H22	121.5
C2—C1—C6	119.64 (16)	C21—C22—H22	121.5
C2—C1—C10	120.62 (17)	C22—C23—C24	121.6 (2)
C6—C1—C10	119.67 (17)	C22—C23—H23	119.2
C1—C2—C3	120.11 (17)	C24—C23—H23	119.2
C1—C2—C7	120.26 (16)	C23—C24—C25	121.1 (3)
C3—C2—C7	119.63 (16)	C23—C24—H24	119.5
C4—C3—C2	119.88 (17)	C25—C24—H24	119.5
C4—C3—C19	120.55 (16)	C26—C25—C24	117.1 (3)
C2—C3—C19	119.42 (17)	C26—C25—H25	121.5
C3—C4—C5	120.07 (17)	C24—C25—H25	121.5
C3—C4—C8	120.62 (17)	C25—C26—C21	121.9 (2)
C5—C4—C8	119.31 (17)	C25—C26—C27	129.7 (2)
C6—C5—C4	119.88 (17)	C21—C26—C27	108.4 (2)
C6—C5—C28	120.05 (16)	O4—C27—N2	125.15 (19)
C4—C5—C28	120.07 (16)	O4—C27—C26	128.9 (2)
C5—C6—C1	120.26 (17)	N2—C27—C26	105.95 (19)
C5—C6—C9	119.51 (17)	N3—C28—C5	112.61 (16)
C1—C6—C9	120.22 (17)	N3—C28—H28A	109.1
C2—C7—Br1	110.86 (14)	C5—C28—H28A	109.1
C2—C7—H7A	109.5	N3—C28—H28B	109.1
Br1—C7—H7A	109.5	C5—C28—H28B	109.1
C2—C7—H7B	109.5	H28A—C28—H28B	107.8
Br1—C7—H7B	109.5	O5—C29—N3	124.4 (2)
H7A—C7—H7B	108.1	O5—C29—C30	129.29 (19)
C4—C8—Br2	110.66 (14)	N3—C29—C30	106.26 (16)
C4—C8—H8A	109.5	C35—C30—C31	122.4 (2)
Br2—C8—H8A	109.5	C35—C30—C29	108.11 (18)
C4—C8—H8B	109.5	C31—C30—C29	129.5 (2)
Br2—C8—H8B	109.5	C30—C31—C32	116.5 (2)
H8A—C8—H8B	108.1	C30—C31—H31	121.8
C6—C9—Br3	110.74 (14)	C32—C31—H31	121.8
C6—C9—H9A	109.5	C33—C32—C31	120.9 (2)
Br3—C9—H9A	109.5	C33—C32—H32	119.5
C6—C9—H9B	109.5	C31—C32—H32	119.5
Br3—C9—H9B	109.5	C32—C33—C34	122.4 (2)
H9A—C9—H9B	108.1	C32—C33—H33	118.8
N1—C10—C1	115.09 (17)	C34—C33—H33	118.8
N1—C10—H10A	108.5	C35—C34—C33	116.9 (2)
C1—C10—H10A	108.5	C35—C34—H34	121.6
N1—C10—H10B	108.5	C33—C34—H34	121.6
C1—C10—H10B	108.5	C34—C35—C30	120.9 (2)
H10A—C10—H10B	107.5	C34—C35—C36	130.8 (2)
O1—C11—N1	124.2 (2)	C30—C35—C36	108.36 (18)
O1—C11—C12	130.1 (2)	O6—C36—N3	124.9 (2)
N1—C11—C12	105.73 (17)	O6—C36—C35	129.2 (2)
C17—C12—C13	121.7 (2)	N3—C36—C35	105.89 (17)
C17—C12—C11	108.37 (19)	C2A—C1A—C6A	120.0
C13—C12—C11	129.9 (2)	C2A—C1A—C7A	125.0
C12—C13—C14	116.9 (3)	C6A—C1A—C7A	114.9
C12—C13—H13	121.5	C3A—C2A—C1A	120.0
C14—C13—H13	121.5	C3A—C2A—H2A	120.0
C15—C14—C13	121.5 (3)	C1A—C2A—H2A	120.0
C15—C14—H14	119.3	C2A—C3A—C4A	120.0
C13—C14—H14	119.3	C2A—C3A—H3A	120.0
C14—C15—C16	121.3 (3)	C4A—C3A—H3A	120.0
C14—C15—H15	119.4	C5A—C4A—C3A	120.0
C16—C15—H15	119.3	C5A—C4A—H4A	120.0
C17—C16—C15	116.5 (3)	C3A—C4A—H4A	120.0
C17—C16—H16	121.8	C6A—C5A—C4A	120.0
C15—C16—H16	121.8	C6A—C5A—H5A	120.0
C12—C17—C16	122.1 (2)	C4A—C5A—H5A	120.0
C12—C17—C18	108.37 (19)	C5A—C6A—C1A	120.0
C16—C17—C18	129.5 (2)	C5A—C6A—H6A	120.0
O2—C18—N1	124.2 (2)	C1A—C6A—H6A	120.0
O2—C18—C17	129.84 (19)	C1A—C7A—H7A1	109.5
N1—C18—C17	105.98 (17)	C1A—C7A—H7A2	109.5
N2—C19—C3	116.12 (16)	H7A1—C7A—H7A2	109.5
N2—C19—H19A	108.3	C1A—C7A—H7A3	109.5
C3—C19—H19A	108.3	H7A1—C7A—H7A3	109.5
N2—C19—H19B	108.3	H7A2—C7A—H7A3	109.5
C3—C19—H19B	108.3
C6—C1—C2—C3	3.0 (3)	C19—N2—C20—O3	−9.9 (3)
C10—C1—C2—C3	−174.19 (18)	C27—N2—C20—C21	7.1 (2)
C6—C1—C2—C7	−176.32 (19)	C19—N2—C20—C21	170.34 (17)
C10—C1—C2—C7	6.5 (3)	O3—C20—C21—C26	176.7 (2)
C1—C2—C3—C4	0.6 (3)	N2—C20—C21—C26	−3.6 (2)
C7—C2—C3—C4	179.86 (18)	O3—C20—C21—C22	−3.3 (4)
C1—C2—C3—C19	−174.93 (18)	N2—C20—C21—C22	176.4 (2)
C7—C2—C3—C19	4.3 (3)	C26—C21—C22—C23	0.9 (4)
C2—C3—C4—C5	−3.7 (3)	C20—C21—C22—C23	−179.1 (2)
C19—C3—C4—C5	171.81 (18)	C21—C22—C23—C24	−1.1 (4)
C2—C3—C4—C8	175.78 (18)	C22—C23—C24—C25	0.6 (4)
C19—C3—C4—C8	−8.8 (3)	C23—C24—C25—C26	0.2 (4)
C3—C4—C5—C6	3.2 (3)	C24—C25—C26—C21	−0.4 (4)
C8—C4—C5—C6	−176.28 (18)	C24—C25—C26—C27	−179.3 (2)
C3—C4—C5—C28	−176.88 (18)	C22—C21—C26—C25	−0.1 (4)
C8—C4—C5—C28	3.7 (3)	C20—C21—C26—C25	179.9 (2)
C4—C5—C6—C1	0.4 (3)	C22—C21—C26—C27	179.0 (2)
C28—C5—C6—C1	−179.56 (18)	C20—C21—C26—C27	−1.0 (2)
C4—C5—C6—C9	−178.73 (19)	C20—N2—C27—O4	170.9 (2)
C28—C5—C6—C9	1.3 (3)	C19—N2—C27—O4	8.4 (3)
C2—C1—C6—C5	−3.4 (3)	C20—N2—C27—C26	−7.7 (2)
C10—C1—C6—C5	173.72 (18)	C19—N2—C27—C26	−170.18 (18)
C2—C1—C6—C9	175.67 (19)	C25—C26—C27—O4	5.7 (4)
C10—C1—C6—C9	−7.2 (3)	C21—C26—C27—O4	−173.3 (2)
C1—C2—C7—Br1	93.3 (2)	C25—C26—C27—N2	−175.8 (2)
C3—C2—C7—Br1	−85.9 (2)	C21—C26—C27—N2	5.3 (2)
C3—C4—C8—Br2	92.48 (19)	C36—N3—C28—C5	−126.16 (18)
C5—C4—C8—Br2	−88.1 (2)	C29—N3—C28—C5	57.0 (2)
C5—C6—C9—Br3	−99.78 (19)	C6—C5—C28—N3	72.1 (2)
C1—C6—C9—Br3	81.1 (2)	C4—C5—C28—N3	−107.8 (2)
C18—N1—C10—C1	129.25 (19)	C36—N3—C29—O5	176.44 (19)
C11—N1—C10—C1	−58.3 (2)	C28—N3—C29—O5	−6.3 (3)
C2—C1—C10—N1	−68.4 (2)	C36—N3—C29—C30	−3.0 (2)
C6—C1—C10—N1	114.4 (2)	C28—N3—C29—C30	174.23 (16)
C18—N1—C11—O1	177.67 (19)	O5—C29—C30—C35	−177.2 (2)
C10—N1—C11—O1	4.5 (3)	N3—C29—C30—C35	2.2 (2)
C18—N1—C11—C12	−1.2 (2)	O5—C29—C30—C31	3.0 (4)
C10—N1—C11—C12	−174.34 (17)	N3—C29—C30—C31	−177.6 (2)
O1—C11—C12—C17	−177.0 (2)	C35—C30—C31—C32	0.3 (3)
N1—C11—C12—C17	1.7 (2)	C29—C30—C31—C32	−179.9 (2)
O1—C11—C12—C13	0.7 (4)	C30—C31—C32—C33	0.5 (3)
N1—C11—C12—C13	179.4 (2)	C31—C32—C33—C34	−0.7 (4)
C17—C12—C13—C14	0.3 (3)	C32—C33—C34—C35	0.0 (3)
C11—C12—C13—C14	−177.1 (2)	C33—C34—C35—C30	0.8 (3)
C12—C13—C14—C15	0.7 (4)	C33—C34—C35—C36	−179.4 (2)
C13—C14—C15—C16	−1.1 (4)	C31—C30—C35—C34	−1.0 (3)
C14—C15—C16—C17	0.4 (4)	C29—C30—C35—C34	179.18 (19)
C13—C12—C17—C16	−1.1 (3)	C31—C30—C35—C36	179.16 (19)
C11—C12—C17—C16	176.8 (2)	C29—C30—C35—C36	−0.7 (2)
C13—C12—C17—C18	−179.57 (19)	C29—N3—C36—O6	−177.11 (19)
C11—C12—C17—C18	−1.6 (2)	C28—N3—C36—O6	5.7 (3)
C15—C16—C17—C12	0.7 (3)	C29—N3—C36—C35	2.6 (2)
C15—C16—C17—C18	178.8 (2)	C28—N3—C36—C35	−174.60 (17)
C11—N1—C18—O2	−179.56 (19)	C34—C35—C36—O6	−1.3 (4)
C10—N1—C18—O2	−6.2 (3)	C30—C35—C36—O6	178.6 (2)
C11—N1—C18—C17	0.2 (2)	C34—C35—C36—N3	179.1 (2)
C10—N1—C18—C17	173.51 (17)	C30—C35—C36—N3	−1.1 (2)
C12—C17—C18—O2	−179.3 (2)	C6A—C1A—C2A—C3A	0.0
C16—C17—C18—O2	2.4 (4)	C7A—C1A—C2A—C3A	−176.9
C12—C17—C18—N1	0.9 (2)	C1A—C2A—C3A—C4A	0.0
C16—C17—C18—N1	−177.4 (2)	C2A—C3A—C4A—C5A	0.0
C27—N2—C19—C3	−74.7 (2)	C3A—C4A—C5A—C6A	0.0
C20—N2—C19—C3	124.55 (19)	C4A—C5A—C6A—C1A	0.0
C4—C3—C19—N2	106.5 (2)	C2A—C1A—C6A—C5A	0.0
C2—C3—C19—N2	−78.0 (2)	C7A—C1A—C6A—C5A	177.2
C27—N2—C20—O3	−173.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O3	0.99	2.47	3.309 (3)	142
C8—H8A···O4	0.99	2.18	3.061 (3)	147
C8—H8B···O5	0.99	2.36	3.036 (3)	125
C8—H8B···O6i	0.99	2.58	3.477 (3)	151
C9—H9A···O1	0.99	2.54	3.308 (3)	135
C10—H10B···Br3	0.99	2.77	3.519 (2)	133
C14—H14···O5ii	0.95	2.49	3.080 (3)	121
C19—H19A···Br1	0.99	2.89	3.642 (2)	133
C24—H24···O2iii	0.95	2.43	3.290 (3)	150
C28—H28A···O6i	0.99	2.58	3.344 (2)	134
C33—H33···Br2iv	0.95	2.77	3.590 (3)	145
C22—H22···Cg1v	0.95	2.66	3.599 (3)	169
C6A—H6A···Cg2	0.95	2.99	3.795 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are centroids of the C1A–C6A and C21–C26 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯O3	0.99	2.47	3.309 (3)	142
C8—H8A⋯O4	0.99	2.18	3.061 (3)	147
C8—H8B⋯O5	0.99	2.36	3.036 (3)	125
C8—H8B⋯O6i	0.99	2.58	3.477 (3)	151
C9—H9A⋯O1	0.99	2.54	3.308 (3)	135
C10—H10B⋯Br3	0.99	2.77	3.519 (2)	133
C14—H14⋯O5ii	0.95	2.49	3.080 (3)	121
C19—H19A⋯Br1	0.99	2.89	3.642 (2)	133
C24—H24⋯O2iii	0.95	2.43	3.290 (3)	150
C28—H28A⋯O6i	0.99	2.58	3.344 (2)	134
C33—H33⋯Br2iv	0.95	2.77	3.590 (3)	145
C22—H22⋯Cg1v	0.95	2.66	3.599 (3)	169
C6A—H6A⋯Cg2	0.95	2.99	3.795 (3)	143

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .