3,3'-[1,2-Phenyl-enebis(methyl-ene)]bis-(1-propyl-benzimidazolium) dibromide hemihydrate.

The asymmetric unit of the title compound, C(28)H(32)N(4) (2+)·2Br(-)·0.5H(2)O, contains one 3,3'-[1,2-phenyl-enebis(methyl-ene)]bis-(1-propyl-benzimidazolium) cation, two bromide anions and one half-mol-ecule of water. In the crystal, the whole 3,3'-[1,2-phen-yl-enebis(methyl-ene)]bis-(1-propyl-benzimidazolium) cation and one of the bromide anions are each disordered over two positions with site-occupancy ratios of 0.751 (6):0.249 (6) and 0.680 (8):0.320 (8). For the major component of the disordered cation, the central benzene ring forms dihedral angles of 83.6 (5) and 88.2 (4)° with its adjacent imidazole rings, while these angles for the minor component are 89.2 (15) and 84.9 (13)°. In the crystal, the cations and anions are linked by C-H⋯Br hydrogen bonds into dimers and then stacked along the c axis. The crystal packing is further stabilized by C-H⋯π and π-π inter-actions [shortest centroid-centroid distance = 3.646 (4) Å].

Related literature

For details and applications (biological and catalytic) of N-heterocyclic carbenes, see: Herrmann (2002 ▶); Winkelmann & Navarro (2010 ▶); Kascatan-Nebioglu et al. (2007 ▶); Ruan et al. (2009 ▶); Barnard et al. (2004 ▶); Teyssot et al. (2009 ▶); Herrmann et al. (1995 ▶, 1996 ▶); Cheng & Trudell (2001 ▶); Lee & Hartwig (2001 ▶); Weskamp et al. (1998 ▶); Choi et al. (2001 ▶). For a related structure, see: Haque et al. (2011 ▶).

Experimental

Crystal data

C28H32N4 2+·2Br−·0.5H2O

M = 593.40

Triclinic,

a = 9.0465 (4) Å

b = 11.4348 (5) Å

c = 14.4143 (7) Å

α = 74.013 (1)°

β = 82.935 (1)°

γ = 70.817 (1)°

V = 1352.96 (11) Å3

Z = 2

Mo Kα radiation

μ = 3.02 mm−1

T = 296 K

0.54 × 0.44 × 0.26 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.290, T max = 0.505

39695 measured reflections

10937 independent reflections

6959 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.133

S = 1.01

10937 reflections

601 parameters

86 restraints

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.47 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812001596/tk5046sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001596/tk5046Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812001596/tk5046Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C28H32N42+·2Br−·0.5H2O	Z = 2
Mr = 593.40	F(000) = 606
Triclinic, P1	Dx = 1.457 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0465 (4) Å	Cell parameters from 9923 reflections
b = 11.4348 (5) Å	θ = 2.6–29.8°
c = 14.4143 (7) Å	µ = 3.02 mm−1
α = 74.013 (1)°	T = 296 K
β = 82.935 (1)°	Block, colourless
γ = 70.817 (1)°	0.54 × 0.44 × 0.26 mm
V = 1352.96 (11) Å3

Bruker APEX DUO CCD area-detector diffractometer	10937 independent reflections
Radiation source: fine-focus sealed tube	6959 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 34.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
Tmin = 0.290, Tmax = 0.505	k = −17→18
39695 measured reflections	l = −22→22

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0782P)2] where P = (Fo2 + 2Fc2)/3
10937 reflections	(Δ/σ)max = 0.001
601 parameters	Δρmax = 0.58 e Å−3
86 restraints	Δρmin = −0.47 e Å−3

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	Occ. (<1)
Br1	0.34759 (2)	0.131872 (19)	0.145379 (13)	0.05001 (8)
Br2	0.20091 (16)	0.6376 (2)	0.43458 (14)	0.0731 (2)	0.680 (8)
Br2X	0.2357 (6)	0.6020 (5)	0.41783 (18)	0.0640 (8)	0.320 (8)
O1W	0.5457 (4)	0.4487 (4)	0.3898 (2)	0.0707 (9)	0.50
H1W1	0.4629	0.4771	0.4182	0.106*	0.50
H2W1	0.5840	0.5051	0.3609	0.106*	0.50
N1	0.6263 (10)	0.2132 (5)	0.8777 (5)	0.0323 (10)	0.751 (6)
N2	0.7191 (8)	0.1608 (5)	1.0205 (4)	0.0353 (9)	0.751 (6)
N3	0.3066 (7)	0.2152 (6)	0.5574 (4)	0.0406 (11)	0.751 (6)
N4	0.1791 (3)	0.1979 (4)	0.4466 (2)	0.0414 (6)	0.751 (6)
C1	0.3017 (6)	0.2661 (11)	0.7142 (3)	0.0332 (10)	0.751 (6)
C2	0.1394 (6)	0.2895 (9)	0.7207 (4)	0.0468 (15)	0.751 (6)
H2A	0.0857	0.3011	0.6663	0.056*	0.751 (6)
C3	0.0599 (7)	0.2953 (12)	0.8070 (5)	0.062 (2)	0.751 (6)
H3A	−0.0482	0.3129	0.8110	0.074*	0.751 (6)
C4	0.1387 (7)	0.2754 (9)	0.8864 (5)	0.065 (2)	0.751 (6)
H4A	0.0830	0.2801	0.9447	0.078*	0.751 (6)
C5	0.2999 (6)	0.2483 (8)	0.8838 (3)	0.0408 (17)	0.751 (6)
H5A	0.3516	0.2336	0.9398	0.049*	0.751 (6)
C6	0.3839 (6)	0.2434 (8)	0.7963 (3)	0.0291 (14)	0.751 (6)
C7	0.5607 (4)	0.2105 (8)	0.7909 (4)	0.0323 (11)	0.751 (6)
H7A	0.6059	0.1257	0.7798	0.039*	0.751 (6)
H7B	0.5907	0.2705	0.7360	0.039*	0.751 (6)
C8	0.6449 (9)	0.3233 (5)	0.8918 (5)	0.0308 (10)	0.751 (6)
C9	0.6122 (10)	0.4465 (6)	0.8342 (6)	0.0428 (13)	0.751 (6)
H9A	0.5759	0.4681	0.7722	0.051*	0.751 (6)
C10	0.6362 (11)	0.5361 (8)	0.8731 (6)	0.063 (2)	0.751 (6)
H10A	0.6081	0.6212	0.8382	0.075*	0.751 (6)
C11	0.7012 (16)	0.5028 (7)	0.9630 (7)	0.058 (2)	0.751 (6)
H11A	0.7271	0.5637	0.9835	0.070*	0.751 (6)
C12	0.7274 (6)	0.3828 (5)	1.0213 (3)	0.0413 (9)	0.751 (6)
H12A	0.7590	0.3634	1.0842	0.050*	0.751 (6)
C13	0.7053 (12)	0.2882 (6)	0.9837 (5)	0.0355 (14)	0.751 (6)
C14	0.6661 (9)	0.1196 (6)	0.9572 (4)	0.0346 (12)	0.751 (6)
H14A	0.6583	0.0379	0.9673	0.042*	0.751 (6)
C15	0.7712 (8)	0.0843 (10)	1.1177 (5)	0.0462 (15)	0.751 (6)
H15A	0.7519	0.0026	1.1306	0.055*	0.751 (6)
H15B	0.7115	0.1285	1.1654	0.055*	0.751 (6)
C16	0.9454 (6)	0.0619 (7)	1.1263 (4)	0.0479 (13)	0.751 (6)
H16A	1.0063	0.0094	1.0838	0.058*	0.751 (6)
H16B	0.9671	0.1431	1.1071	0.058*	0.751 (6)
C17	0.9910 (10)	−0.0049 (10)	1.2302 (5)	0.0598 (17)	0.751 (6)
H17A	1.1016	−0.0232	1.2352	0.090*	0.751 (6)
H17B	0.9651	−0.0833	1.2497	0.090*	0.751 (6)
H17C	0.9352	0.0498	1.2715	0.090*	0.751 (6)
C18	0.3809 (7)	0.2683 (9)	0.6143 (4)	0.0477 (14)	0.751 (6)
H18A	0.3746	0.3557	0.5803	0.057*	0.751 (6)
H18B	0.4908	0.2188	0.6210	0.057*	0.751 (6)
C19	0.3297 (11)	0.0853 (6)	0.5715 (5)	0.0409 (10)	0.751 (6)
C20	0.4148 (6)	−0.0197 (5)	0.6376 (4)	0.0501 (10)	0.751 (6)
H20A	0.4737	−0.0124	0.6831	0.060*	0.751 (6)
C21	0.4078 (5)	−0.1384 (5)	0.6326 (3)	0.0627 (10)	0.751 (6)
H21A	0.4601	−0.2120	0.6775	0.075*	0.751 (6)
C22	0.3234 (6)	−0.1483 (5)	0.5615 (4)	0.0636 (12)	0.751 (6)
H22A	0.3247	−0.2290	0.5588	0.076*	0.751 (6)
C23	0.2397 (6)	−0.0436 (5)	0.4960 (4)	0.0533 (11)	0.751 (6)
H23A	0.1818	−0.0505	0.4498	0.064*	0.751 (6)
C24	0.2454 (5)	0.0750 (4)	0.5021 (2)	0.0405 (7)	0.751 (6)
C25	0.2186 (5)	0.2804 (4)	0.4814 (3)	0.0419 (7)	0.751 (6)
H25A	0.1893	0.3686	0.4564	0.050*	0.751 (6)
C26	0.0792 (3)	0.2281 (3)	0.36446 (18)	0.0526 (8)	0.751 (6)
H26A	0.1372	0.1801	0.3185	0.063*	0.751 (6)
H26B	−0.0115	0.1994	0.3878	0.063*	0.751 (6)
C27	0.0247 (6)	0.3644 (4)	0.3139 (3)	0.0668 (10)	0.751 (6)
H27A	0.1137	0.3943	0.2883	0.080*	0.751 (6)
H27B	−0.0348	0.4141	0.3585	0.080*	0.751 (6)
C28	−0.0789 (6)	0.3819 (7)	0.2310 (4)	0.0825 (17)	0.751 (6)
H28A	−0.1778	0.4453	0.2366	0.124*	0.751 (6)
H28B	−0.0957	0.3021	0.2344	0.124*	0.751 (6)
H28C	−0.0278	0.4090	0.1703	0.124*	0.751 (6)
N1X	0.616 (3)	0.2328 (16)	0.8647 (14)	0.030 (3)	0.249 (6)
N2X	0.712 (3)	0.1779 (16)	1.0092 (12)	0.048 (4)	0.249 (6)
N3X	0.332 (2)	0.2288 (16)	0.5494 (11)	0.033 (2)	0.249 (6)
N4X	0.2008 (10)	0.2460 (10)	0.4266 (6)	0.0447 (19)	0.249 (6)
C1X	0.289 (2)	0.280 (4)	0.7097 (12)	0.045 (4)	0.249 (6)
C2X	0.131 (2)	0.313 (3)	0.7235 (11)	0.045 (4)	0.249 (6)
H2XA	0.0685	0.3455	0.6698	0.054*	0.249 (6)
C3X	0.0585 (18)	0.302 (3)	0.8143 (10)	0.044 (5)	0.249 (6)
H3XA	−0.0492	0.3162	0.8201	0.053*	0.249 (6)
C4X	0.1405 (12)	0.2703 (18)	0.8960 (10)	0.029 (3)	0.249 (6)
H4XA	0.0912	0.2687	0.9567	0.035*	0.249 (6)
C5X	0.3064 (14)	0.240 (2)	0.8822 (10)	0.048 (6)	0.249 (6)
H5XA	0.3687	0.2137	0.9354	0.058*	0.249 (6)
C6X	0.3755 (16)	0.249 (3)	0.7906 (10)	0.040 (6)	0.249 (6)
C7X	0.5551 (18)	0.214 (3)	0.7805 (14)	0.043 (5)	0.249 (6)
H7XA	0.6001	0.1259	0.7771	0.052*	0.249 (6)
H7XB	0.5847	0.2682	0.7214	0.052*	0.249 (6)
C8X	0.622 (3)	0.3458 (13)	0.8809 (14)	0.025 (2)	0.249 (6)
C9X	0.588 (3)	0.4690 (14)	0.8238 (16)	0.028 (2)	0.249 (6)
H9XA	0.5322	0.4963	0.7675	0.033*	0.249 (6)
C10X	0.644 (2)	0.5502 (16)	0.8580 (13)	0.034 (2)	0.249 (6)
H10B	0.6383	0.6312	0.8192	0.041*	0.249 (6)
C11X	0.706 (5)	0.512 (2)	0.9476 (18)	0.054 (7)	0.249 (6)
H11B	0.7169	0.5735	0.9742	0.065*	0.249 (6)
C12X	0.7528 (18)	0.3874 (17)	0.9997 (9)	0.044 (3)	0.249 (6)
H12B	0.8241	0.3576	1.0486	0.053*	0.249 (6)
C13X	0.683 (3)	0.3077 (16)	0.9728 (15)	0.026 (2)	0.249 (6)
C14X	0.678 (3)	0.1349 (15)	0.9396 (10)	0.026 (2)	0.249 (6)
H14B	0.6953	0.0492	0.9426	0.031*	0.249 (6)
C15X	0.760 (2)	0.106 (3)	1.1083 (13)	0.040 (4)	0.249 (6)
H15C	0.7075	0.0406	1.1293	0.048*	0.249 (6)
H15D	0.7204	0.1639	1.1498	0.048*	0.249 (6)
C16X	0.931 (2)	0.041 (2)	1.1260 (13)	0.049 (3)	0.249 (6)
H16C	0.9888	0.0957	1.0861	0.058*	0.249 (6)
H16D	0.9629	−0.0378	1.1052	0.058*	0.249 (6)
C17X	0.977 (3)	0.009 (3)	1.2318 (13)	0.049 (3)	0.249 (6)
H17D	1.0859	−0.0393	1.2375	0.073*	0.249 (6)
H17E	0.9154	−0.0405	1.2728	0.073*	0.249 (6)
H17F	0.9581	0.0869	1.2509	0.073*	0.249 (6)
C18X	0.385 (2)	0.285 (3)	0.6152 (12)	0.059 (6)	0.249 (6)
H18C	0.3772	0.3729	0.5834	0.071*	0.249 (6)
H18D	0.4941	0.2384	0.6287	0.071*	0.249 (6)
C19X	0.317 (3)	0.1102 (16)	0.5559 (15)	0.048 (5)	0.249 (6)
C20X	0.3762 (18)	−0.0076 (15)	0.6166 (13)	0.062 (4)	0.249 (6)
H20B	0.4266	−0.0160	0.6717	0.074*	0.249 (6)
C21X	0.3613 (18)	−0.1175 (13)	0.5957 (10)	0.069 (4)	0.249 (6)
H21B	0.4040	−0.1983	0.6359	0.082*	0.249 (6)
C22X	0.2820 (16)	−0.1025 (15)	0.5145 (13)	0.061 (4)	0.249 (6)
H22B	0.2701	−0.1742	0.5015	0.073*	0.249 (6)
C23X	0.2211 (12)	0.0149 (13)	0.4533 (11)	0.058 (3)	0.249 (6)
H23B	0.1706	0.0235	0.3983	0.070*	0.249 (6)
C24X	0.2365 (14)	0.1207 (10)	0.4751 (8)	0.037 (2)	0.249 (6)
C25X	0.2511 (14)	0.3105 (12)	0.4735 (9)	0.048 (3)	0.249 (6)
H25B	0.2330	0.3985	0.4561	0.057*	0.249 (6)
C26X	0.1198 (10)	0.3095 (10)	0.3319 (5)	0.053 (2)	0.249 (6)
H26C	0.1340	0.3932	0.3068	0.064*	0.249 (6)
H26D	0.1691	0.2590	0.2859	0.064*	0.249 (6)
C27X	−0.0422 (12)	0.3242 (15)	0.3394 (8)	0.076 (3)	0.249 (6)
H27C	−0.0919	0.3835	0.3791	0.091*	0.249 (6)
H27D	−0.0554	0.2422	0.3738	0.091*	0.249 (6)
C28X	−0.1297 (18)	0.370 (2)	0.2470 (12)	0.076 (3)	0.249 (6)
H28D	−0.2237	0.3462	0.2584	0.114*	0.249 (6)
H28E	−0.0649	0.3326	0.1984	0.114*	0.249 (6)
H28F	−0.1563	0.4618	0.2256	0.114*	0.249 (6)

	U11	U22	U33	U12	U13	U23
Br1	0.06026 (12)	0.04747 (12)	0.04622 (11)	−0.02155 (9)	−0.00117 (8)	−0.01236 (8)
Br2	0.0514 (3)	0.1019 (5)	0.0664 (4)	−0.0187 (4)	−0.0086 (2)	−0.0250 (5)
Br2X	0.0688 (11)	0.0842 (15)	0.0438 (6)	−0.0383 (10)	−0.0028 (6)	−0.0058 (5)
O1W	0.0696 (19)	0.071 (2)	0.0677 (19)	−0.0031 (17)	−0.0239 (15)	−0.0253 (17)
N1	0.0333 (18)	0.035 (2)	0.031 (2)	−0.0109 (19)	−0.0093 (12)	−0.0079 (19)
N2	0.0299 (16)	0.0447 (17)	0.0320 (16)	−0.0112 (14)	−0.0050 (13)	−0.0093 (15)
N3	0.037 (2)	0.062 (2)	0.0303 (13)	−0.0243 (14)	−0.0014 (14)	−0.0140 (13)
N4	0.0440 (13)	0.056 (2)	0.0321 (11)	−0.0230 (13)	−0.0038 (9)	−0.0141 (13)
C1	0.0260 (12)	0.043 (3)	0.0333 (16)	−0.0110 (13)	−0.0001 (12)	−0.0139 (17)
C2	0.0289 (14)	0.063 (4)	0.054 (2)	−0.0108 (15)	−0.0045 (12)	−0.0249 (19)
C3	0.032 (3)	0.087 (5)	0.075 (4)	−0.015 (3)	−0.004 (2)	−0.035 (3)
C4	0.057 (3)	0.081 (5)	0.055 (3)	−0.017 (3)	0.019 (2)	−0.028 (3)
C5	0.043 (3)	0.054 (3)	0.0253 (16)	−0.015 (2)	0.0067 (15)	−0.0135 (18)
C6	0.031 (2)	0.034 (3)	0.0238 (15)	−0.0086 (17)	−0.0060 (14)	−0.0087 (15)
C7	0.0235 (15)	0.044 (3)	0.0308 (18)	−0.0091 (14)	−0.0001 (12)	−0.0141 (16)
C8	0.023 (3)	0.032 (2)	0.0346 (18)	−0.003 (2)	−0.0052 (13)	−0.0078 (14)
C9	0.038 (3)	0.037 (3)	0.045 (2)	0.000 (2)	−0.0073 (16)	−0.007 (2)
C10	0.069 (3)	0.044 (3)	0.076 (4)	−0.025 (2)	0.014 (2)	−0.014 (2)
C11	0.057 (3)	0.066 (5)	0.072 (4)	−0.026 (4)	0.006 (3)	−0.044 (3)
C12	0.0401 (19)	0.0617 (19)	0.036 (2)	−0.0250 (15)	0.0103 (14)	−0.0278 (16)
C13	0.025 (3)	0.047 (3)	0.0335 (19)	−0.006 (2)	−0.0060 (13)	−0.0138 (19)
C14	0.0310 (17)	0.0408 (19)	0.031 (2)	−0.0164 (14)	−0.0028 (18)	−0.0002 (14)
C15	0.042 (2)	0.060 (3)	0.0313 (18)	−0.0149 (19)	−0.0085 (14)	−0.0015 (18)
C16	0.0298 (13)	0.073 (3)	0.0413 (16)	−0.0172 (17)	−0.0036 (11)	−0.0129 (18)
C17	0.053 (3)	0.069 (3)	0.052 (2)	−0.012 (2)	−0.0166 (17)	−0.008 (2)
C18	0.046 (2)	0.081 (3)	0.036 (2)	−0.037 (2)	0.0074 (16)	−0.027 (2)
C19	0.039 (2)	0.054 (2)	0.0310 (17)	−0.016 (2)	−0.0008 (13)	−0.0121 (18)
C20	0.042 (3)	0.065 (2)	0.0364 (16)	−0.0147 (16)	0.0010 (14)	−0.0046 (13)
C21	0.063 (2)	0.062 (3)	0.047 (2)	−0.0124 (18)	0.0070 (15)	0.0001 (17)
C22	0.070 (3)	0.063 (3)	0.061 (3)	−0.028 (2)	0.017 (2)	−0.018 (2)
C23	0.055 (2)	0.062 (3)	0.050 (2)	−0.025 (2)	0.0036 (18)	−0.019 (2)
C24	0.0387 (12)	0.049 (2)	0.0324 (15)	−0.0130 (17)	−0.0011 (12)	−0.0088 (14)
C25	0.0417 (17)	0.056 (2)	0.0315 (12)	−0.0183 (13)	−0.0068 (11)	−0.0109 (12)
C26	0.0545 (14)	0.0700 (19)	0.0407 (12)	−0.0213 (14)	−0.0154 (10)	−0.0170 (13)
C27	0.080 (3)	0.072 (2)	0.0559 (18)	−0.030 (2)	−0.0285 (18)	−0.0083 (16)
C28	0.098 (4)	0.081 (3)	0.071 (3)	−0.024 (3)	−0.052 (3)	−0.006 (2)
N1X	0.025 (3)	0.026 (4)	0.027 (4)	−0.001 (3)	−0.010 (3)	0.011 (3)
N2X	0.043 (6)	0.059 (8)	0.028 (4)	−0.015 (5)	−0.018 (3)	0.016 (4)
N3X	0.023 (4)	0.055 (5)	0.030 (4)	−0.024 (3)	0.003 (3)	−0.011 (3)
N4X	0.040 (3)	0.061 (6)	0.041 (4)	−0.022 (4)	−0.003 (3)	−0.016 (4)
C1X	0.048 (6)	0.049 (8)	0.040 (5)	−0.015 (5)	−0.016 (4)	−0.008 (4)
C2X	0.048 (6)	0.049 (8)	0.040 (5)	−0.015 (5)	−0.016 (4)	−0.008 (4)
C3X	0.028 (8)	0.061 (10)	0.040 (7)	−0.013 (7)	0.022 (6)	−0.016 (6)
C4X	0.014 (4)	0.054 (8)	0.024 (4)	−0.017 (4)	0.003 (3)	−0.010 (4)
C5X	0.025 (6)	0.050 (9)	0.075 (11)	−0.013 (6)	−0.019 (6)	−0.014 (7)
C6X	0.021 (6)	0.038 (9)	0.066 (11)	−0.015 (5)	0.016 (5)	−0.018 (8)
C7X	0.057 (8)	0.053 (10)	0.031 (5)	−0.020 (6)	−0.022 (4)	−0.017 (5)
C8X	0.016 (5)	0.024 (5)	0.029 (4)	0.008 (4)	−0.014 (3)	−0.010 (4)
C9X	0.026 (5)	0.012 (4)	0.036 (4)	0.005 (4)	−0.015 (3)	0.002 (3)
C10X	0.042 (5)	0.034 (6)	0.036 (4)	−0.021 (4)	−0.002 (4)	−0.011 (4)
C11X	0.077 (15)	0.044 (10)	0.044 (6)	−0.028 (10)	−0.003 (7)	−0.003 (6)
C12X	0.035 (5)	0.076 (8)	0.025 (5)	−0.017 (4)	0.017 (3)	−0.026 (5)
C13X	0.018 (6)	0.022 (4)	0.033 (5)	0.000 (4)	−0.008 (3)	−0.003 (3)
C14X	0.033 (4)	0.032 (5)	0.019 (4)	−0.022 (4)	0.007 (3)	−0.006 (4)
C15X	0.023 (4)	0.061 (9)	0.031 (5)	−0.019 (5)	−0.005 (3)	0.006 (4)
C16X	0.049 (5)	0.071 (7)	0.033 (4)	−0.033 (5)	−0.013 (3)	0.000 (4)
C17X	0.049 (5)	0.071 (7)	0.033 (4)	−0.033 (5)	−0.013 (3)	0.000 (4)
C18X	0.069 (10)	0.071 (10)	0.047 (8)	−0.022 (7)	−0.026 (7)	−0.019 (7)
C19X	0.033 (6)	0.058 (8)	0.045 (8)	−0.011 (6)	0.009 (5)	−0.005 (5)
C20X	0.031 (6)	0.096 (11)	0.059 (10)	−0.023 (6)	0.005 (5)	−0.019 (8)
C21X	0.071 (10)	0.054 (7)	0.050 (8)	−0.006 (7)	0.023 (7)	0.010 (7)
C22X	0.058 (8)	0.061 (10)	0.061 (9)	−0.019 (7)	0.010 (6)	−0.016 (8)
C23X	0.045 (4)	0.071 (8)	0.077 (7)	−0.021 (5)	0.004 (5)	−0.046 (7)
C24X	0.044 (4)	0.031 (5)	0.033 (5)	−0.004 (5)	−0.010 (4)	−0.009 (4)
C25X	0.039 (5)	0.063 (7)	0.053 (5)	−0.022 (4)	−0.001 (4)	−0.025 (5)
C26X	0.051 (4)	0.068 (6)	0.040 (4)	−0.015 (4)	−0.001 (3)	−0.019 (4)
C27X	0.066 (5)	0.090 (8)	0.063 (5)	0.002 (5)	−0.023 (4)	−0.028 (5)
C28X	0.066 (5)	0.090 (8)	0.063 (5)	0.002 (5)	−0.023 (4)	−0.028 (5)

O1W—H1W1	0.8199	C28—H28C	0.9600
O1W—H2W1	0.8200	N1X—C14X	1.343 (13)
N1—C14	1.328 (6)	N1X—C8X	1.393 (13)
N1—C8	1.394 (5)	N1X—C7X	1.484 (13)
N1—C7	1.461 (5)	N2X—C14X	1.337 (13)
N2—C14	1.333 (5)	N2X—C13X	1.377 (13)
N2—C13	1.374 (6)	N2X—C15X	1.477 (13)
N2—C15	1.473 (6)	N3X—C25X	1.337 (13)
N3—C25	1.329 (5)	N3X—C19X	1.385 (13)
N3—C19	1.390 (6)	N3X—C18X	1.478 (14)
N3—C18	1.473 (5)	N4X—C25X	1.334 (11)
N4—C25	1.340 (4)	N4X—C24X	1.359 (11)
N4—C24	1.386 (4)	N4X—C26X	1.510 (10)
N4—C26	1.473 (3)	C1X—C2X	1.362 (13)
C1—C6	1.392 (4)	C1X—C6X	1.382 (13)
C1—C2	1.400 (4)	C1X—C18X	1.520 (14)
C1—C18	1.526 (4)	C2X—C3X	1.382 (13)
C2—C3	1.364 (6)	C2X—H2XA	0.9300
C2—H2A	0.9300	C3X—C4X	1.368 (13)
C3—C4	1.349 (7)	C3X—H3XA	0.9300
C3—H3A	0.9300	C4X—C5X	1.426 (11)
C4—C5	1.386 (6)	C4X—H4XA	0.9300
C4—H4A	0.9300	C5X—C6X	1.382 (13)
C5—C6	1.395 (4)	C5X—H5XA	0.9300
C5—H5A	0.9300	C6X—C7X	1.539 (13)
C6—C7	1.516 (4)	C7X—H7XA	0.9700
C7—H7A	0.9700	C7X—H7XB	0.9700
C7—H7B	0.9700	C8X—C9X	1.377 (13)
C8—C9	1.380 (6)	C8X—C13X	1.399 (13)
C8—C13	1.398 (6)	C9X—C10X	1.408 (12)
C9—C10	1.379 (7)	C9X—H9XA	0.9300
C9—H9A	0.9300	C10X—C11X	1.372 (14)
C10—C11	1.393 (7)	C10X—H10B	0.9300
C10—H10A	0.9300	C11X—C12X	1.362 (15)
C11—C12	1.359 (6)	C11X—H11B	0.9300
C11—H11A	0.9300	C12X—C13X	1.418 (14)
C12—C13	1.413 (5)	C12X—H12B	0.9300
C12—H12A	0.9300	C14X—H14B	0.9300
C14—H14A	0.9300	C15X—C16X	1.497 (15)
C15—C16	1.526 (6)	C15X—H15C	0.9700
C15—H15A	0.9700	C15X—H15D	0.9700
C15—H15B	0.9700	C16X—C17X	1.543 (14)
C16—C17	1.521 (6)	C16X—H16C	0.9700
C16—H16A	0.9700	C16X—H16D	0.9700
C16—H16B	0.9700	C17X—H17D	0.9600
C17—H17A	0.9600	C17X—H17E	0.9600
C17—H17B	0.9600	C17X—H17F	0.9600
C17—H17C	0.9600	C18X—H18C	0.9700
C18—H18A	0.9700	C18X—H18D	0.9700
C18—H18B	0.9700	C19X—C20X	1.364 (14)
C19—C20	1.373 (6)	C19X—C24X	1.403 (13)
C19—C24	1.381 (5)	C20X—C21X	1.420 (15)
C20—C21	1.402 (6)	C20X—H20B	0.9300
C20—H20A	0.9300	C21X—C22X	1.390 (15)
C21—C22	1.400 (6)	C21X—H21B	0.9300
C21—H21A	0.9300	C22X—C23X	1.365 (14)
C22—C23	1.362 (6)	C22X—H22B	0.9300
C22—H22A	0.9300	C23X—C24X	1.384 (11)
C23—C24	1.402 (6)	C23X—H23B	0.9300
C23—H23A	0.9300	C25X—H25B	0.9300
C25—H25A	0.9300	C26X—C27X	1.413 (12)
C26—C27	1.470 (5)	C26X—H26C	0.9700
C26—H26A	0.9700	C26X—H26D	0.9700
C26—H26B	0.9700	C27X—C28X	1.509 (13)
C27—C28	1.538 (4)	C27X—H27C	0.9700
C27—H27A	0.9700	C27X—H27D	0.9700
C27—H27B	0.9700	C28X—H28D	0.9600
C28—H28A	0.9600	C28X—H28E	0.9600
C28—H28B	0.9600	C28X—H28F	0.9600
H1W1—O1W—H2W1	111.9	C25X—N3X—C19X	107.1 (11)
C14—N1—C8	108.7 (4)	C25X—N3X—C18X	116.9 (14)
C14—N1—C7	127.8 (5)	C19X—N3X—C18X	134.5 (15)
C8—N1—C7	123.3 (5)	C25X—N4X—C24X	110.4 (8)
C14—N2—C13	109.3 (4)	C25X—N4X—C26X	122.1 (10)
C14—N2—C15	124.9 (6)	C24X—N4X—C26X	127.5 (8)
C13—N2—C15	125.6 (5)	C2X—C1X—C6X	116.5 (12)
C25—N3—C19	109.4 (4)	C2X—C1X—C18X	128.5 (14)
C25—N3—C18	126.4 (5)	C6X—C1X—C18X	114.6 (13)
C19—N3—C18	124.0 (5)	C1X—C2X—C3X	122.5 (14)
C25—N4—C24	108.9 (3)	C1X—C2X—H2XA	118.8
C25—N4—C26	127.4 (3)	C3X—C2X—H2XA	118.8
C24—N4—C26	123.7 (3)	C4X—C3X—C2X	122.0 (13)
C6—C1—C2	120.3 (4)	C4X—C3X—H3XA	119.0
C6—C1—C18	122.8 (4)	C2X—C3X—H3XA	119.0
C2—C1—C18	116.9 (4)	C3X—C4X—C5X	115.8 (11)
C3—C2—C1	120.0 (5)	C3X—C4X—H4XA	122.1
C3—C2—H2A	120.0	C5X—C4X—H4XA	122.1
C1—C2—H2A	120.0	C6X—C5X—C4X	120.7 (11)
C4—C3—C2	119.9 (5)	C6X—C5X—H5XA	119.7
C4—C3—H3A	120.1	C4X—C5X—H5XA	119.7
C2—C3—H3A	120.1	C1X—C6X—C5X	121.9 (11)
C3—C4—C5	122.0 (6)	C1X—C6X—C7X	119.8 (12)
C3—C4—H4A	119.0	C5X—C6X—C7X	118.2 (12)
C5—C4—H4A	119.0	N1X—C7X—C6X	109.7 (14)
C4—C5—C6	119.4 (4)	N1X—C7X—H7XA	109.7
C4—C5—H5A	120.3	C6X—C7X—H7XA	109.7
C6—C5—H5A	120.3	N1X—C7X—H7XB	109.7
C1—C6—C5	118.4 (4)	C6X—C7X—H7XB	109.7
C1—C6—C7	120.6 (4)	H7XA—C7X—H7XB	108.2
C5—C6—C7	121.0 (4)	C9X—C8X—N1X	132.2 (13)
N1—C7—C6	113.7 (4)	C9X—C8X—C13X	123.7 (12)
N1—C7—H7A	108.8	N1X—C8X—C13X	104.0 (11)
C6—C7—H7A	108.8	C8X—C9X—C10X	114.3 (13)
N1—C7—H7B	108.8	C8X—C9X—H9XA	122.8
C6—C7—H7B	108.8	C10X—C9X—H9XA	122.8
H7A—C7—H7B	107.7	C11X—C10X—C9X	121.0 (15)
C9—C8—N1	131.6 (5)	C11X—C10X—H10B	119.5
C9—C8—C13	122.4 (5)	C9X—C10X—H10B	119.5
N1—C8—C13	106.0 (4)	C12X—C11X—C10X	123.7 (17)
C10—C9—C8	116.7 (6)	C12X—C11X—H11B	118.2
C10—C9—H9A	121.7	C10X—C11X—H11B	118.2
C8—C9—H9A	121.7	C11X—C12X—C13X	114.0 (15)
C9—C10—C11	122.0 (6)	C11X—C12X—H12B	123.0
C9—C10—H10A	119.0	C13X—C12X—H12B	123.0
C11—C10—H10A	119.0	N2X—C13X—C8X	109.8 (11)
C12—C11—C10	121.0 (5)	N2X—C13X—C12X	127.4 (15)
C12—C11—H11A	119.5	C8X—C13X—C12X	118.9 (13)
C10—C11—H11A	119.5	N2X—C14X—N1X	110.5 (12)
C11—C12—C13	118.2 (5)	N2X—C14X—H14B	124.7
C11—C12—H12A	120.9	N1X—C14X—H14B	124.7
C13—C12—H12A	120.9	N2X—C15X—C16X	118.6 (16)
N2—C13—C8	106.4 (4)	N2X—C15X—H15C	107.7
N2—C13—C12	134.2 (5)	C16X—C15X—H15C	107.7
C8—C13—C12	119.2 (5)	N2X—C15X—H15D	107.7
N1—C14—N2	109.4 (5)	C16X—C15X—H15D	107.7
N1—C14—H14A	125.3	H15C—C15X—H15D	107.1
N2—C14—H14A	125.3	C15X—C16X—C17X	115.2 (16)
N2—C15—C16	110.8 (6)	C15X—C16X—H16C	108.5
N2—C15—H15A	109.5	C17X—C16X—H16C	108.5
C16—C15—H15A	109.5	C15X—C16X—H16D	108.5
N2—C15—H15B	109.5	C17X—C16X—H16D	108.5
C16—C15—H15B	109.5	H16C—C16X—H16D	107.5
H15A—C15—H15B	108.1	C16X—C17X—H17D	109.5
C17—C16—C15	109.3 (5)	C16X—C17X—H17E	109.5
C17—C16—H16A	109.8	H17D—C17X—H17E	109.5
C15—C16—H16A	109.8	C16X—C17X—H17F	109.5
C17—C16—H16B	109.8	H17D—C17X—H17F	109.5
C15—C16—H16B	109.8	H17E—C17X—H17F	109.5
H16A—C16—H16B	108.3	N3X—C18X—C1X	112.2 (16)
N3—C18—C1	111.4 (5)	N3X—C18X—H18C	109.2
N3—C18—H18A	109.4	C1X—C18X—H18C	109.2
C1—C18—H18A	109.4	N3X—C18X—H18D	109.2
N3—C18—H18B	109.4	C1X—C18X—H18D	109.2
C1—C18—H18B	109.4	H18C—C18X—H18D	107.9
H18A—C18—H18B	108.0	C20X—C19X—N3X	132.9 (13)
C20—C19—C24	122.3 (4)	C20X—C19X—C24X	118.9 (12)
C20—C19—N3	131.5 (4)	N3X—C19X—C24X	107.8 (11)
C24—C19—N3	106.2 (5)	C19X—C20X—C21X	120.0 (13)
C19—C20—C21	116.1 (4)	C19X—C20X—H20B	120.0
C19—C20—H20A	122.0	C21X—C20X—H20B	120.0
C21—C20—H20A	122.0	C22X—C21X—C20X	119.1 (12)
C22—C21—C20	121.3 (4)	C22X—C21X—H21B	120.4
C22—C21—H21A	119.3	C20X—C21X—H21B	120.4
C20—C21—H21A	119.3	C23X—C22X—C21X	121.5 (12)
C23—C22—C21	122.1 (4)	C23X—C22X—H22B	119.2
C23—C22—H22A	118.9	C21X—C22X—H22B	119.2
C21—C22—H22A	118.9	C22X—C23X—C24X	118.4 (11)
C22—C23—C24	116.3 (4)	C22X—C23X—H23B	120.8
C22—C23—H23A	121.8	C24X—C23X—H23B	120.8
C24—C23—H23A	121.8	N4X—C24X—C23X	132.6 (10)
C19—C24—N4	106.8 (4)	N4X—C24X—C19X	105.0 (9)
C19—C24—C23	121.8 (4)	C23X—C24X—C19X	122.0 (11)
N4—C24—C23	131.4 (3)	N4X—C25X—N3X	109.3 (11)
N3—C25—N4	108.7 (4)	N4X—C25X—H25B	125.3
N3—C25—H25A	125.7	N3X—C25X—H25B	125.3
N4—C25—H25A	125.7	C27X—C26X—N4X	113.5 (8)
C27—C26—N4	114.6 (3)	C27X—C26X—H26C	108.9
C27—C26—H26A	108.6	N4X—C26X—H26C	108.9
N4—C26—H26A	108.6	C27X—C26X—H26D	108.9
C27—C26—H26B	108.6	N4X—C26X—H26D	108.9
N4—C26—H26B	108.6	H26C—C26X—H26D	107.7
H26A—C26—H26B	107.6	C26X—C27X—C28X	117.7 (11)
C26—C27—C28	109.0 (3)	C26X—C27X—H27C	107.9
C26—C27—H27A	109.9	C28X—C27X—H27C	107.9
C28—C27—H27A	109.9	C26X—C27X—H27D	107.9
C26—C27—H27B	109.9	C28X—C27X—H27D	107.9
C28—C27—H27B	109.9	H27C—C27X—H27D	107.2
H27A—C27—H27B	108.3	C27X—C28X—H28D	109.5
C14X—N1X—C8X	109.0 (11)	C27X—C28X—H28E	109.5
C14X—N1X—C7X	122.3 (15)	H28D—C28X—H28E	109.5
C8X—N1X—C7X	128.7 (15)	C27X—C28X—H28F	109.5
C14X—N2X—C13X	106.3 (12)	H28D—C28X—H28F	109.5
C14X—N2X—C15X	128.1 (16)	H28E—C28X—H28F	109.5
C13X—N2X—C15X	125.4 (16)
C6—C1—C2—C3	2.7 (12)	C6X—C1X—C2X—C3X	−8(4)
C18—C1—C2—C3	−176.8 (11)	C18X—C1X—C2X—C3X	179 (4)
C1—C2—C3—C4	−1.6 (16)	C1X—C2X—C3X—C4X	8(4)
C2—C3—C4—C5	−0.3 (18)	C2X—C3X—C4X—C5X	−5(4)
C3—C4—C5—C6	1.1 (15)	C3X—C4X—C5X—C6X	3(3)
C2—C1—C6—C5	−1.9 (12)	C2X—C1X—C6X—C5X	6(4)
C18—C1—C6—C5	177.5 (9)	C18X—C1X—C6X—C5X	−180 (3)
C2—C1—C6—C7	176.4 (7)	C2X—C1X—C6X—C7X	−178 (2)
C18—C1—C6—C7	−4.1 (14)	C18X—C1X—C6X—C7X	−4(4)
C4—C5—C6—C1	0.0 (13)	C4X—C5X—C6X—C1X	−4(4)
C4—C5—C6—C7	−178.3 (8)	C4X—C5X—C6X—C7X	−180 (2)
C14—N1—C7—C6	86.5 (11)	C14X—N1X—C7X—C6X	100 (3)
C8—N1—C7—C6	−88.0 (10)	C8X—N1X—C7X—C6X	−80 (3)
C1—C6—C7—N1	169.1 (8)	C1X—C6X—C7X—N1X	159 (3)
C5—C6—C7—N1	−12.7 (11)	C5X—C6X—C7X—N1X	−25 (3)
C14—N1—C8—C9	−176.2 (10)	C14X—N1X—C8X—C9X	173 (3)
C7—N1—C8—C9	−0.7 (15)	C7X—N1X—C8X—C9X	−7(5)
C14—N1—C8—C13	2.6 (10)	C14X—N1X—C8X—C13X	−3(3)
C7—N1—C8—C13	178.0 (8)	C7X—N1X—C8X—C13X	177 (3)
N1—C8—C9—C10	176.1 (10)	N1X—C8X—C9X—C10X	−165 (3)
C13—C8—C9—C10	−2.5 (14)	C13X—C8X—C9X—C10X	10 (4)
C8—C9—C10—C11	4.7 (16)	C8X—C9X—C10X—C11X	−9(4)
C9—C10—C11—C12	−7.6 (19)	C9X—C10X—C11X—C12X	16 (6)
C10—C11—C12—C13	7.7 (16)	C10X—C11X—C12X—C13X	−22 (5)
C14—N2—C13—C8	−1.9 (10)	C14X—N2X—C13X—C8X	4(3)
C15—N2—C13—C8	−177.0 (7)	C15X—N2X—C13X—C8X	−173 (2)
C14—N2—C13—C12	172.6 (10)	C14X—N2X—C13X—C12X	−154 (3)
C15—N2—C13—C12	−2.5 (16)	C15X—N2X—C13X—C12X	30 (5)
C9—C8—C13—N2	178.5 (9)	C9X—C8X—C13X—N2X	−177 (3)
N1—C8—C13—N2	−0.4 (10)	N1X—C8X—C13X—N2X	0(3)
C9—C8—C13—C12	3.0 (14)	C9X—C8X—C13X—C12X	−17 (4)
N1—C8—C13—C12	−175.9 (8)	N1X—C8X—C13X—C12X	159 (2)
C11—C12—C13—N2	−179.4 (11)	C11X—C12X—C13X—N2X	177 (3)
C11—C12—C13—C8	−5.5 (13)	C11X—C12X—C13X—C8X	22 (4)
C8—N1—C14—N2	−3.8 (10)	C13X—N2X—C14X—N1X	−6(3)
C7—N1—C14—N2	−179.0 (7)	C15X—N2X—C14X—N1X	170 (2)
C13—N2—C14—N1	3.6 (10)	C8X—N1X—C14X—N2X	6(3)
C15—N2—C14—N1	178.7 (7)	C7X—N1X—C14X—N2X	−175 (2)
C14—N2—C15—C16	115.6 (9)	C14X—N2X—C15X—C16X	89 (3)
C13—N2—C15—C16	−70.0 (11)	C13X—N2X—C15X—C16X	−96 (4)
N2—C15—C16—C17	174.0 (8)	N2X—C15X—C16X—C17X	159 (2)
C25—N3—C18—C1	109.2 (8)	C25X—N3X—C18X—C1X	106 (2)
C19—N3—C18—C1	−76.3 (10)	C19X—N3X—C18X—C1X	−58 (4)
C6—C1—C18—N3	144.6 (9)	C2X—C1X—C18X—N3X	−47 (4)
C2—C1—C18—N3	−36.0 (10)	C6X—C1X—C18X—N3X	140 (3)
C25—N3—C19—C20	177.8 (9)	C25X—N3X—C19X—C20X	178 (3)
C18—N3—C19—C20	2.4 (15)	C18X—N3X—C19X—C20X	−17 (5)
C25—N3—C19—C24	−2.4 (9)	C25X—N3X—C19X—C24X	6(3)
C18—N3—C19—C24	−177.7 (5)	C18X—N3X—C19X—C24X	171 (2)
C24—C19—C20—C21	−1.8 (12)	N3X—C19X—C20X—C21X	−169 (3)
N3—C19—C20—C21	178.0 (9)	C24X—C19X—C20X—C21X	2(3)
C19—C20—C21—C22	2.5 (9)	C19X—C20X—C21X—C22X	−2(3)
C20—C21—C22—C23	−2.5 (8)	C20X—C21X—C22X—C23X	1(2)
C21—C22—C23—C24	1.5 (7)	C21X—C22X—C23X—C24X	−1.6 (19)
C20—C19—C24—N4	−178.1 (7)	C25X—N4X—C24X—C23X	−174.1 (13)
N3—C19—C24—N4	2.1 (8)	C26X—N4X—C24X—C23X	5(2)
C20—C19—C24—C23	1.0 (12)	C25X—N4X—C24X—C19X	−1.1 (18)
N3—C19—C24—C23	−178.8 (5)	C26X—N4X—C24X—C19X	177.5 (15)
C25—N4—C24—C19	−1.1 (6)	C22X—C23X—C24X—N4X	174.1 (13)
C26—N4—C24—C19	−179.9 (5)	C22X—C23X—C24X—C19X	2(2)
C25—N4—C24—C23	180.0 (4)	C20X—C19X—C24X—N4X	−176 (2)
C26—N4—C24—C23	1.2 (6)	N3X—C19X—C24X—N4X	−3(2)
C22—C23—C24—C19	−0.8 (8)	C20X—C19X—C24X—C23X	−2(3)
C22—C23—C24—N4	178.0 (4)	N3X—C19X—C24X—C23X	171.1 (16)
C19—N3—C25—N4	1.8 (7)	C24X—N4X—C25X—N3X	4.9 (15)
C18—N3—C25—N4	177.0 (5)	C26X—N4X—C25X—N3X	−173.8 (11)
C24—N4—C25—N3	−0.4 (5)	C19X—N3X—C25X—N4X	−7(2)
C26—N4—C25—N3	178.3 (4)	C18X—N3X—C25X—N4X	−174.8 (14)
C25—N4—C26—C27	3.0 (5)	C25X—N4X—C26X—C27X	−108.4 (13)
C24—N4—C26—C27	−178.4 (4)	C24X—N4X—C26X—C27X	73.1 (14)
N4—C26—C27—C28	−179.5 (3)	N4X—C26X—C27X—C28X	−172.1 (13)

Cg6 and Cg8 are the centroids of the N1X/C8X/C13X/N2X/C14X and C1X–C6X rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···Br1i	0.93	2.87	3.665 (4)	144
C7—H7A···Br1ii	0.97	2.75	3.596 (9)	146
C14—H14A···Br1ii	0.93	2.87	3.618 (7)	138
C20—H20A···Br1ii	0.93	2.87	3.699 (6)	148
C5—H5A···Cg6	0.93	2.82	3.405 (14)	122
C28—H28A···Cg8iii	0.96	2.99	3.607 (15)	123

Table 1

Hydrogen-bond geometry (Å, °)

Cg6 and Cg8 are the centroids of the N1X/C8X/C13X/N2X/C14X and C1X–C6X rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯Br1i	0.93	2.87	3.665 (4)	144
C7—H7A⋯Br1ii	0.97	2.75	3.596 (9)	146
C14—H14A⋯Br1ii	0.93	2.87	3.618 (7)	138
C20—H20A⋯Br1ii	0.93	2.87	3.699 (6)	148
C5—H5A⋯Cg6	0.93	2.82	3.405 (14)	122
C28—H28A⋯Cg8iii	0.96	2.99	3.607 (15)	123

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