2-(2-Benzyl-oxyphen-yl)-1H-benzimid-azole.

The asymmetric unit of the title compound, C(20)H(16)N(2)O, contains two mol-ecules. The dihedral angles between the benzimidazole ring systems and the attached benzene rings are 10.6 (5) and 13.7 (5)°. The conformers are linked by bifurcated three-centre hydrogen bonds, forming chains along the diagonal of the ab plane. The packing is further stabilized by π-π and C-H⋯π inter-actions.

Related literature

For general background, see: Desiraju & Steiner (1999 ▶); Lehn (1990 ▶); Saenger (1984 ▶); Wakelin (1986 ▶). For related structures, see: Estrada-Soto et al. (2006 ▶); Moreno-Diaz et al. (2006 ▶); Navarrete-Vázquez et al. (2006 ▶).

Experimental

Crystal data

C20H16N2O

M = 300.35

Monoclinic,

a = 11.526 (2) Å

b = 17.210 (3) Å

c = 15.866 (3) Å

β = 90.52 (3)°

V = 3147.0 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.31 × 0.21 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.976, T max = 0.987

7808 measured reflections

2830 independent reflections

2691 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.100

S = 1.17

2830 reflections

423 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus NT (Bruker, 2001 ▶); data reduction: SAINT-Plus NT; program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT; software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004510/sj2464sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808004510/sj2464Isup2.hkl

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

C20H16N2O	F000 = 1264
Mr = 300.35	Dx = 1.268 Mg m−3
Monoclinic, Cc	Melting point: 415.5 K
Hall symbol: C -2yc	Mo Kα radiation λ = 0.71073 Å
a = 11.526 (2) Å	Cell parameters from 68 reflections
b = 17.210 (3) Å	θ = 2.6–25.2º
c = 15.866 (3) Å	µ = 0.08 mm−1
β = 90.52 (3)º	T = 293 (2) K
V = 3147.0 (11) Å3	Rectangular, colourless
Z = 8	0.31 × 0.21 × 0.17 mm

Bruker SMART CCD area-detector diffractometer	2830 independent reflections
Radiation source: fine-focus sealed tube	2691 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.038
Detector resolution: 8.3 pixels mm-1	θmax = 25.2º
T = 293(2) K	θmin = 2.1º
φ and ω scans	h = −13→13
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)	k = −20→11
Tmin = 0.976, Tmax = 0.987	l = −19→16
7808 measured reflections

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0376P)2 + 0.4648P] where P = (Fo2 + 2Fc2)/3
S = 1.17	(Δ/σ)max < 0.001
2830 reflections	Δρmax = 0.20 e Å−3
423 parameters	Δρmin = −0.20 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
C1	0.0469 (3)	0.1160 (2)	0.3249 (2)	0.0179 (8)
C2	−0.0279 (3)	0.1316 (2)	0.3917 (2)	0.0213 (8)
H2	−0.0755	0.1752	0.3920	0.026*
C3	−0.0273 (3)	0.0789 (2)	0.4571 (2)	0.0234 (8)
H3	−0.0735	0.0880	0.5038	0.028*
C4	0.0419 (3)	0.0115 (2)	0.4547 (2)	0.0243 (9)
H4	0.0389	−0.0234	0.4994	0.029*
C5	0.1134 (3)	−0.0040 (2)	0.3885 (2)	0.0241 (9)
H5	0.1589	−0.0486	0.3878	0.029*
C6	0.1160 (3)	0.0492 (2)	0.3217 (2)	0.0176 (8)
C7	0.1528 (3)	0.1149 (2)	0.2093 (2)	0.0161 (7)
C8	0.2074 (3)	0.1393 (2)	0.1295 (2)	0.0175 (8)
C9	0.1951 (3)	0.2138 (2)	0.0950 (2)	0.0183 (8)
C10	0.2567 (3)	0.2342 (2)	0.0234 (2)	0.0251 (9)
H10	0.2501	0.2840	0.0012	0.030*
C11	0.3279 (3)	0.1801 (2)	−0.0149 (2)	0.0250 (9)
H11	0.3693	0.1943	−0.0625	0.030*
C12	0.3387 (3)	0.1057 (2)	0.0163 (2)	0.0254 (9)
H12	0.3854	0.0694	−0.0107	0.031*
C13	0.2787 (3)	0.0857 (2)	0.0886 (2)	0.0219 (8)
H13	0.2860	0.0357	0.1103	0.026*
C14	0.1043 (3)	0.3400 (2)	0.1037 (2)	0.0219 (8)
H14A	0.0319	0.3604	0.1252	0.026*
H14B	0.0976	0.3380	0.0427	0.026*
C15	0.2018 (3)	0.3952 (2)	0.1275 (2)	0.0199 (8)
C16	0.2041 (3)	0.4669 (2)	0.0885 (2)	0.0229 (8)
H16	0.1473	0.4796	0.0488	0.027*
C17	0.2905 (3)	0.5204 (2)	0.1082 (2)	0.0260 (9)
H17	0.2918	0.5684	0.0813	0.031*
C18	0.3752 (4)	0.5020 (2)	0.1683 (2)	0.0294 (9)
H18	0.4334	0.5374	0.1818	0.035*
C19	0.3714 (3)	0.4304 (2)	0.2071 (2)	0.0276 (9)
H19	0.4272	0.4180	0.2476	0.033*
C20	0.2863 (3)	0.3768 (2)	0.1872 (2)	0.0234 (9)
H20	0.2856	0.3286	0.2136	0.028*
C21	0.7495 (3)	0.6470 (2)	0.7012 (2)	0.0180 (8)
C22	0.6466 (3)	0.6399 (2)	0.6541 (2)	0.0224 (8)
H22	0.6103	0.5922	0.6463	0.027*
C23	0.6018 (3)	0.7076 (2)	0.6200 (2)	0.0268 (9)
H23	0.5331	0.7054	0.5889	0.032*
C24	0.6575 (4)	0.7794 (2)	0.6310 (2)	0.0274 (9)
H24	0.6257	0.8235	0.6062	0.033*
C25	0.7588 (3)	0.7861 (2)	0.6781 (2)	0.0237 (9)
H25	0.7943	0.8340	0.6865	0.028*
C26	0.8057 (3)	0.7180 (2)	0.7126 (2)	0.0191 (8)
C27	0.9128 (3)	0.6312 (2)	0.7734 (2)	0.0183 (8)
C28	1.0124 (3)	0.5952 (2)	0.8170 (2)	0.0196 (8)
C29	1.0358 (3)	0.5147 (2)	0.8146 (2)	0.0238 (8)
C30	1.1374 (3)	0.4861 (2)	0.8502 (2)	0.0270 (9)
H30	1.1533	0.4332	0.8480	0.032*
C31	1.2149 (3)	0.5359 (3)	0.8887 (2)	0.0301 (10)
H31	1.2836	0.5164	0.9115	0.036*
C32	1.1918 (3)	0.6145 (3)	0.8941 (2)	0.0308 (10)
H32	1.2437	0.6473	0.9217	0.037*
C33	1.0913 (3)	0.6440 (2)	0.8583 (2)	0.0247 (9)
H33	1.0761	0.6970	0.8618	0.030*
C34	0.9791 (4)	0.3883 (2)	0.7630 (2)	0.0288 (9)
H34A	1.0596	0.3828	0.7468	0.035*
H34B	0.9314	0.3686	0.7171	0.035*
C35	0.9579 (3)	0.3394 (2)	0.8407 (2)	0.0232 (8)
C36	0.8786 (4)	0.3607 (2)	0.9019 (3)	0.0324 (10)
H36	0.8390	0.4076	0.8970	0.039*
C37	0.8581 (4)	0.3123 (3)	0.9702 (3)	0.0367 (11)
H37	0.8049	0.3271	1.0110	0.044*
C38	0.9165 (4)	0.2422 (3)	0.9780 (3)	0.0320 (10)
H38	0.9033	0.2102	1.0241	0.038*
C39	0.9938 (4)	0.2205 (2)	0.9173 (3)	0.0321 (10)
H39	1.0320	0.1731	0.9221	0.039*
C40	1.0159 (3)	0.2682 (2)	0.8486 (2)	0.0260 (9)
H40	1.0689	0.2528	0.8080	0.031*
N1	0.0711 (3)	0.15646 (17)	0.25172 (18)	0.0174 (6)
N2	0.1813 (3)	0.04949 (17)	0.24872 (17)	0.0191 (7)
N3	0.8195 (3)	0.59233 (18)	0.74010 (19)	0.0197 (7)
N4	0.9075 (3)	0.70755 (17)	0.75867 (17)	0.0180 (7)
O1	0.1204 (2)	0.26267 (14)	0.13499 (15)	0.0230 (6)
O2	0.9538 (2)	0.46984 (15)	0.77489 (16)	0.0266 (6)
H1	0.038 (3)	0.202 (2)	0.241 (2)	0.015 (9)*
H3A	0.807 (4)	0.545 (3)	0.740 (3)	0.034 (12)*

	U11	U22	U33	U12	U13	U23
C1	0.022 (2)	0.0171 (18)	0.0143 (17)	−0.0041 (16)	−0.0013 (14)	0.0012 (14)
C2	0.022 (2)	0.0161 (18)	0.026 (2)	−0.0017 (16)	0.0013 (15)	0.0000 (16)
C3	0.024 (2)	0.027 (2)	0.0197 (18)	−0.0024 (17)	0.0014 (15)	−0.0030 (17)
C4	0.032 (2)	0.023 (2)	0.0186 (18)	−0.0037 (18)	−0.0018 (16)	0.0068 (15)
C5	0.028 (2)	0.0168 (19)	0.027 (2)	−0.0005 (17)	−0.0035 (16)	0.0012 (17)
C6	0.018 (2)	0.0155 (18)	0.0189 (18)	−0.0015 (15)	−0.0006 (15)	−0.0024 (15)
C7	0.0180 (19)	0.0121 (18)	0.0182 (17)	−0.0026 (15)	−0.0024 (14)	−0.0031 (14)
C8	0.0142 (18)	0.0204 (19)	0.0179 (17)	−0.0069 (15)	−0.0038 (14)	−0.0025 (15)
C9	0.021 (2)	0.0167 (18)	0.0170 (18)	0.0002 (16)	−0.0015 (15)	−0.0009 (15)
C10	0.029 (2)	0.020 (2)	0.026 (2)	−0.0009 (18)	−0.0023 (16)	0.0019 (17)
C11	0.027 (2)	0.028 (2)	0.0198 (19)	−0.0064 (18)	0.0087 (16)	−0.0008 (16)
C12	0.028 (2)	0.024 (2)	0.0248 (19)	0.0042 (18)	0.0069 (16)	−0.0085 (17)
C13	0.023 (2)	0.0181 (19)	0.0249 (19)	0.0030 (17)	−0.0031 (15)	−0.0018 (16)
C14	0.027 (2)	0.0172 (19)	0.0217 (19)	0.0021 (17)	0.0031 (15)	0.0033 (16)
C15	0.023 (2)	0.019 (2)	0.0179 (18)	0.0047 (16)	0.0056 (15)	−0.0003 (15)
C16	0.028 (2)	0.0211 (19)	0.0199 (18)	0.0051 (17)	−0.0026 (16)	−0.0024 (16)
C17	0.035 (2)	0.018 (2)	0.026 (2)	0.0010 (18)	0.0052 (17)	−0.0031 (16)
C18	0.031 (2)	0.030 (2)	0.027 (2)	−0.0011 (19)	0.0056 (17)	−0.0133 (18)
C19	0.018 (2)	0.040 (2)	0.025 (2)	0.0062 (18)	−0.0013 (15)	−0.0056 (18)
C20	0.024 (2)	0.025 (2)	0.0206 (19)	0.0045 (17)	0.0041 (16)	0.0008 (16)
C21	0.0165 (19)	0.0150 (17)	0.0225 (18)	−0.0006 (15)	0.0019 (14)	0.0017 (15)
C22	0.022 (2)	0.0182 (19)	0.0270 (19)	−0.0031 (16)	−0.0006 (15)	0.0009 (16)
C23	0.021 (2)	0.028 (2)	0.032 (2)	0.0030 (18)	−0.0043 (16)	0.0006 (18)
C24	0.036 (2)	0.023 (2)	0.024 (2)	0.0075 (18)	0.0045 (17)	0.0053 (17)
C25	0.029 (2)	0.0189 (19)	0.023 (2)	−0.0057 (17)	0.0084 (16)	0.0035 (16)
C26	0.020 (2)	0.0211 (19)	0.0163 (17)	−0.0003 (16)	0.0039 (14)	−0.0010 (15)
C27	0.0184 (19)	0.0175 (18)	0.0191 (17)	−0.0065 (16)	0.0060 (14)	−0.0012 (15)
C28	0.0171 (19)	0.0230 (19)	0.0186 (17)	−0.0029 (17)	0.0068 (14)	−0.0019 (16)
C29	0.026 (2)	0.027 (2)	0.0177 (18)	0.0016 (18)	0.0014 (15)	−0.0022 (17)
C30	0.027 (2)	0.029 (2)	0.0249 (19)	0.0037 (18)	−0.0020 (16)	0.0024 (18)
C31	0.018 (2)	0.048 (3)	0.024 (2)	0.001 (2)	−0.0043 (16)	0.012 (2)
C32	0.027 (2)	0.041 (3)	0.024 (2)	−0.0114 (19)	−0.0042 (17)	0.0071 (19)
C33	0.022 (2)	0.029 (2)	0.0226 (18)	−0.0045 (18)	0.0018 (16)	0.0004 (17)
C34	0.032 (2)	0.023 (2)	0.031 (2)	0.0075 (19)	−0.0077 (18)	−0.0064 (17)
C35	0.020 (2)	0.024 (2)	0.026 (2)	−0.0005 (16)	−0.0070 (16)	−0.0040 (16)
C36	0.024 (2)	0.030 (2)	0.044 (2)	0.0056 (19)	−0.0039 (19)	−0.007 (2)
C37	0.023 (2)	0.053 (3)	0.034 (2)	−0.014 (2)	0.0047 (18)	−0.009 (2)
C38	0.033 (3)	0.029 (2)	0.034 (2)	−0.016 (2)	−0.0012 (19)	0.0032 (19)
C39	0.033 (2)	0.023 (2)	0.040 (2)	−0.0030 (19)	−0.0056 (19)	−0.0005 (19)
C40	0.025 (2)	0.025 (2)	0.029 (2)	0.0021 (18)	0.0007 (16)	−0.0053 (18)
N1	0.0187 (17)	0.0113 (15)	0.0222 (16)	0.0033 (13)	0.0026 (12)	0.0008 (13)
N2	0.0202 (17)	0.0152 (15)	0.0219 (16)	0.0006 (13)	−0.0023 (13)	−0.0016 (13)
N3	0.0213 (17)	0.0133 (16)	0.0244 (16)	−0.0015 (14)	−0.0008 (13)	0.0004 (14)
N4	0.0190 (16)	0.0200 (15)	0.0149 (15)	−0.0029 (14)	0.0011 (12)	−0.0004 (12)
O1	0.0251 (14)	0.0162 (13)	0.0279 (14)	0.0043 (12)	0.0073 (11)	0.0033 (11)
O2	0.0246 (15)	0.0203 (14)	0.0346 (15)	0.0045 (12)	−0.0103 (12)	−0.0028 (12)

C1—N1	1.384 (4)	C21—C26	1.394 (5)
C1—C2	1.399 (5)	C21—C22	1.401 (5)
C1—C6	1.400 (5)	C22—C23	1.382 (5)
C2—C3	1.378 (5)	C22—H22	0.9300
C2—H2	0.9300	C23—C24	1.403 (6)
C3—C4	1.408 (5)	C23—H23	0.9300
C3—H3	0.9300	C24—C25	1.385 (5)
C4—C5	1.367 (5)	C24—H24	0.9300
C4—H4	0.9300	C25—C26	1.399 (5)
C5—C6	1.401 (5)	C25—H25	0.9300
C5—H5	0.9300	C26—N4	1.388 (4)
C6—N2	1.387 (4)	C27—N4	1.335 (4)
C7—N2	1.327 (4)	C27—N3	1.368 (4)
C7—N1	1.365 (4)	C27—C28	1.472 (5)
C7—C8	1.480 (5)	C28—C33	1.398 (5)
C8—C13	1.399 (5)	C28—C29	1.412 (5)
C8—C9	1.402 (5)	C29—O2	1.370 (4)
C9—O1	1.365 (4)	C29—C30	1.386 (5)
C9—C10	1.390 (5)	C30—C31	1.376 (5)
C10—C11	1.384 (5)	C30—H30	0.9300
C10—H10	0.9300	C31—C32	1.381 (6)
C11—C12	1.379 (5)	C31—H31	0.9300
C11—H11	0.9300	C32—C33	1.382 (5)
C12—C13	1.389 (5)	C32—H32	0.9300
C12—H12	0.9300	C33—H33	0.9300
C13—H13	0.9300	C34—O2	1.447 (4)
C14—O1	1.431 (4)	C34—C35	1.514 (5)
C14—C15	1.517 (5)	C34—H34A	0.9700
C14—H14A	0.9700	C34—H34B	0.9700
C14—H14B	0.9700	C35—C36	1.388 (5)
C15—C16	1.382 (5)	C35—C40	1.401 (5)
C15—C20	1.388 (5)	C36—C37	1.389 (6)
C16—C17	1.389 (5)	C36—H36	0.9300
C16—H16	0.9300	C37—C38	1.387 (6)
C17—C18	1.395 (5)	C37—H37	0.9300
C17—H17	0.9300	C38—C39	1.370 (6)
C18—C19	1.378 (6)	C38—H38	0.9300
C18—H18	0.9300	C39—C40	1.390 (6)
C19—C20	1.381 (5)	C39—H39	0.9300
C19—H19	0.9300	C40—H40	0.9300
C20—H20	0.9300	N1—H1	0.89 (4)
C21—N3	1.382 (5)	N3—H3A	0.83 (4)
N1—C1—C2	132.0 (3)	C21—C22—H22	121.8
N1—C1—C6	105.3 (3)	C22—C23—C24	121.7 (4)
C2—C1—C6	122.6 (3)	C22—C23—H23	119.2
C3—C2—C1	116.4 (4)	C24—C23—H23	119.2
C3—C2—H2	121.8	C25—C24—C23	121.5 (4)
C1—C2—H2	121.8	C25—C24—H24	119.2
C2—C3—C4	121.4 (4)	C23—C24—H24	119.2
C2—C3—H3	119.3	C24—C25—C26	117.5 (3)
C4—C3—H3	119.3	C24—C25—H25	121.2
C5—C4—C3	121.8 (3)	C26—C25—H25	121.2
C5—C4—H4	119.1	N4—C26—C21	110.2 (3)
C3—C4—H4	119.1	N4—C26—C25	129.5 (3)
C4—C5—C6	118.1 (3)	C21—C26—C25	120.3 (3)
C4—C5—H5	121.0	N4—C27—N3	112.3 (3)
C6—C5—H5	121.0	N4—C27—C28	122.0 (3)
N2—C6—C1	109.9 (3)	N3—C27—C28	125.6 (3)
N2—C6—C5	130.5 (3)	C33—C28—C29	118.6 (4)
C1—C6—C5	119.6 (3)	C33—C28—C27	117.9 (3)
N2—C7—N1	112.4 (3)	C29—C28—C27	123.3 (3)
N2—C7—C8	122.6 (3)	O2—C29—C30	124.4 (3)
N1—C7—C8	125.0 (3)	O2—C29—C28	115.7 (3)
C13—C8—C9	118.7 (3)	C30—C29—C28	119.9 (4)
C13—C8—C7	117.8 (3)	C31—C30—C29	120.2 (4)
C9—C8—C7	123.5 (3)	C31—C30—H30	119.9
O1—C9—C10	123.7 (3)	C29—C30—H30	119.9
O1—C9—C8	116.3 (3)	C30—C31—C32	120.8 (4)
C10—C9—C8	120.0 (3)	C30—C31—H31	119.6
C11—C10—C9	119.9 (3)	C32—C31—H31	119.6
C11—C10—H10	120.1	C31—C32—C33	119.8 (4)
C9—C10—H10	120.1	C31—C32—H32	120.1
C12—C11—C10	121.3 (3)	C33—C32—H32	120.1
C12—C11—H11	119.3	C32—C33—C28	120.7 (4)
C10—C11—H11	119.3	C32—C33—H33	119.7
C11—C12—C13	118.8 (4)	C28—C33—H33	119.7
C11—C12—H12	120.6	O2—C34—C35	113.5 (3)
C13—C12—H12	120.6	O2—C34—H34A	108.9
C12—C13—C8	121.3 (3)	C35—C34—H34A	108.9
C12—C13—H13	119.4	O2—C34—H34B	108.9
C8—C13—H13	119.4	C35—C34—H34B	108.9
O1—C14—C15	113.7 (3)	H34A—C34—H34B	107.7
O1—C14—H14A	108.8	C36—C35—C40	119.1 (4)
C15—C14—H14A	108.8	C36—C35—C34	122.3 (3)
O1—C14—H14B	108.8	C40—C35—C34	118.6 (3)
C15—C14—H14B	108.8	C35—C36—C37	120.3 (4)
H14A—C14—H14B	107.7	C35—C36—H36	119.9
C16—C15—C20	119.5 (4)	C37—C36—H36	119.9
C16—C15—C14	117.7 (3)	C38—C37—C36	120.4 (4)
C20—C15—C14	122.8 (3)	C38—C37—H37	119.8
C15—C16—C17	120.5 (3)	C36—C37—H37	119.8
C15—C16—H16	119.7	C39—C38—C37	119.6 (4)
C17—C16—H16	119.7	C39—C38—H38	120.2
C16—C17—C18	120.0 (4)	C37—C38—H38	120.2
C16—C17—H17	120.0	C38—C39—C40	121.0 (4)
C18—C17—H17	120.0	C38—C39—H39	119.5
C19—C18—C17	118.9 (4)	C40—C39—H39	119.5
C19—C18—H18	120.6	C39—C40—C35	119.7 (4)
C17—C18—H18	120.6	C39—C40—H40	120.1
C18—C19—C20	121.3 (4)	C35—C40—H40	120.1
C18—C19—H19	119.3	C7—N1—C1	107.1 (3)
C20—C19—H19	119.3	C7—N1—H1	131 (2)
C19—C20—C15	119.8 (4)	C1—N1—H1	121 (2)
C19—C20—H20	120.1	C7—N2—C6	105.3 (3)
C15—C20—H20	120.1	C27—N3—C21	107.0 (3)
N3—C21—C26	105.6 (3)	C27—N3—H3A	128 (3)
N3—C21—C22	131.8 (3)	C21—N3—H3A	125 (3)
C26—C21—C22	122.5 (3)	C27—N4—C26	104.9 (3)
C23—C22—C21	116.5 (3)	C9—O1—C14	119.4 (3)
C23—C22—H22	121.8	C29—O2—C34	117.9 (3)
N1—C1—C2—C3	−177.8 (4)	N4—C27—C28—C33	12.9 (5)
C6—C1—C2—C3	2.5 (5)	N3—C27—C28—C33	−170.4 (3)
C1—C2—C3—C4	−2.4 (5)	N4—C27—C28—C29	−163.0 (3)
C2—C3—C4—C5	1.4 (6)	N3—C27—C28—C29	13.7 (5)
C3—C4—C5—C6	−0.3 (5)	C33—C28—C29—O2	178.5 (3)
N1—C1—C6—N2	0.5 (4)	C27—C28—C29—O2	−5.7 (5)
C2—C1—C6—N2	−179.7 (3)	C33—C28—C29—C30	−2.3 (5)
N1—C1—C6—C5	178.7 (3)	C27—C28—C29—C30	173.6 (3)
C2—C1—C6—C5	−1.5 (5)	O2—C29—C30—C31	180.0 (4)
C4—C5—C6—N2	178.2 (4)	C28—C29—C30—C31	0.8 (5)
C4—C5—C6—C1	0.4 (5)	C29—C30—C31—C32	1.3 (6)
N2—C7—C8—C13	9.5 (5)	C30—C31—C32—C33	−1.8 (6)
N1—C7—C8—C13	−172.1 (3)	C31—C32—C33—C28	0.2 (6)
N2—C7—C8—C9	−167.8 (3)	C29—C28—C33—C32	1.8 (5)
N1—C7—C8—C9	10.6 (5)	C27—C28—C33—C32	−174.3 (3)
C13—C8—C9—O1	177.0 (3)	O2—C34—C35—C36	26.2 (5)
C7—C8—C9—O1	−5.7 (5)	O2—C34—C35—C40	−157.3 (3)
C13—C8—C9—C10	−2.5 (5)	C40—C35—C36—C37	0.6 (6)
C7—C8—C9—C10	174.8 (3)	C34—C35—C36—C37	177.1 (4)
O1—C9—C10—C11	−177.9 (3)	C35—C36—C37—C38	−0.1 (6)
C8—C9—C10—C11	1.6 (5)	C36—C37—C38—C39	−0.7 (6)
C9—C10—C11—C12	0.5 (6)	C37—C38—C39—C40	1.0 (6)
C10—C11—C12—C13	−1.5 (6)	C38—C39—C40—C35	−0.4 (6)
C11—C12—C13—C8	0.5 (6)	C36—C35—C40—C39	−0.4 (5)
C9—C8—C13—C12	1.5 (5)	C34—C35—C40—C39	−176.9 (3)
C7—C8—C13—C12	−176.0 (3)	N2—C7—N1—C1	1.5 (4)
O1—C14—C15—C16	169.2 (3)	C8—C7—N1—C1	−177.0 (3)
O1—C14—C15—C20	−11.9 (5)	C2—C1—N1—C7	179.1 (4)
C20—C15—C16—C17	0.5 (5)	C6—C1—N1—C7	−1.2 (4)
C14—C15—C16—C17	179.4 (3)	N1—C7—N2—C6	−1.2 (4)
C15—C16—C17—C18	−0.6 (5)	C8—C7—N2—C6	177.4 (3)
C16—C17—C18—C19	0.0 (5)	C1—C6—N2—C7	0.4 (4)
C17—C18—C19—C20	0.6 (6)	C5—C6—N2—C7	−177.6 (4)
C18—C19—C20—C15	−0.7 (5)	N4—C27—N3—C21	0.1 (4)
C16—C15—C20—C19	0.2 (5)	C28—C27—N3—C21	−176.8 (3)
C14—C15—C20—C19	−178.7 (3)	C26—C21—N3—C27	0.4 (4)
N3—C21—C22—C23	−176.6 (4)	C22—C21—N3—C27	176.7 (4)
C26—C21—C22—C23	−0.9 (5)	N3—C27—N4—C26	−0.6 (4)
C21—C22—C23—C24	0.8 (6)	C28—C27—N4—C26	176.5 (3)
C22—C23—C24—C25	−1.3 (6)	C21—C26—N4—C27	0.9 (4)
C23—C24—C25—C26	1.7 (5)	C25—C26—N4—C27	−177.9 (4)
N3—C21—C26—N4	−0.8 (4)	C10—C9—O1—C14	−1.1 (5)
C22—C21—C26—N4	−177.6 (3)	C8—C9—O1—C14	179.4 (3)
N3—C21—C26—C25	178.1 (3)	C15—C14—O1—C9	−78.0 (4)
C22—C21—C26—C25	1.4 (5)	C30—C29—O2—C34	−5.5 (5)
C24—C25—C26—N4	176.9 (3)	C28—C29—O2—C34	173.7 (3)
C24—C25—C26—C21	−1.7 (5)	C35—C34—O2—C29	80.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.89 (4)	2.20 (3)	2.667 (4)	112 (3)
N1—H1···N4i	0.89 (4)	2.18 (3)	3.008 (4)	154 (3)
N3—H3A···O2	0.83 (4)	2.20 (5)	2.670 (4)	117 (4)
N3—H3A···N2ii	0.83 (4)	2.18 (5)	2.918 (4)	148 (4)
C14—H14A···Cg1i	0.97	2.88	3.736 (4)	148
C14—H14B···Cg4iii	0.97	2.92	3.721 (4)	141
Cg3—···.Cg2i	.	.	3.859 (2)	.

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C27/N4/C26/C21/N3 imidazole ring, and Cg2, Cg3 and Cg4 are the centroids of the C28–C33, C15–C20 and C35–C40 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.89 (4)	2.20 (3)	2.667 (4)	112 (3)
N1—H1⋯N4i	0.89 (4)	2.18 (3)	3.008 (4)	154 (3)
N3—H3A⋯O2	0.83 (4)	2.20 (5)	2.670 (4)	117 (4)
N3—H3A⋯N2ii	0.83 (4)	2.18 (5)	2.918 (4)	148 (4)
C14—H14A⋯Cg1i	0.97	2.88	3.736 (4)	148
C14—H14B⋯Cg4iii	0.97	2.92	3.721 (4)	141
Cg3⋯Cg2i			3.859 (2)

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