Synthesis and characterization of a novel long-alkyl-chain ester-substituted benzimidazole gelator and its octan-1-ol solvate

The synthesis of a novel benzimidazole derivative with a long-chain-ester substituent, namely methyl 8-[4-(1H-benzimidazol-2-yl)phen­oxy]octa­noate, (3), is reported. Ester (3) shows evidence of aggregation in solution and weak gelation ability with toluene. The octan-1-ol solvate, methyl 8-[4-(1H-benz­imidazol-2-yl)phen­oxy]octa­noate octan-1-ol monosolvate, C₂₂H₂₆N₂O₃·C₈H₁₈O, (4), exhibits a four-mol­ecule hydrogen-bonded motif in the solid state, with N—H...O hydrogen bonds between benzimidazole mol­ecules and O—H...N hydrogen bonds between the octan-1-ol solvent mol­ecules and the benzimidazole unit. The alkyl chains of the ester and the octan-1-ol mol­ecules are in unfolded conformations. The phenyl­ene ring is canted by 10.27 (6)° from the plane of the benzimidazole ring system. H...C contacts make up 20.7% of the Hirshfeld surface coverage. Weak C—H...π inter­actions involving the benzimidazole alkyl chain and three aromatic rings are observed.

Computing details

Data collection: APEX2 (Bruker, 2013); cell refinement: APEX2 (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Methyl 8-[4-(1H-benzimidazol-2-yl)phenoxy]octanoate octan-1-ol monosolvate

Crystal data

C22H26N2O3·C8H18O	Z = 2
Mr = 496.67	F(000) = 540
Triclinic, P1	Dx = 1.145 Mg m^−3
a = 9.2021 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2022 (16) Å	Cell parameters from 5163 reflections
c = 16.532 (3) Å	θ = 2.2–24.1°
α = 74.490 (6)°	µ = 0.08 mm^−1
β = 78.452 (6)°	T = 200 K
γ = 76.849 (6)°	Plate, clear colourless
V = 1440.2 (5) Å^3	0.80 × 0.60 × 0.10 mm

Data collection

Bruker SMART X2S benchtop diffractometer	5023 independent reflections
Radiation source: sealed microfocus tube	3677 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.032
Detector resolution: 8.3330 pixels mm^-1	θmax = 25.0°, θmin = 2.3°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −12→11
Tmin = 0.93, Tmax = 0.99	l = −14→19
13949 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.128	w = 1/[σ^2(Fo^2) + (0.0617P)^2 + 0.2226P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
5023 reflections	Δρmax = 0.19 e Å^−3
381 parameters	Δρmin = −0.17 e Å^−3
3 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0108 (16)

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)
O1	0.84209 (13)	0.96487 (11)	0.88862 (8)	0.0564 (3)
O2	0.70722 (14)	1.89008 (11)	1.14286 (8)	0.0598 (3)
O3	0.86421 (14)	1.69407 (12)	1.19013 (8)	0.0607 (4)
O4	0.30350 (18)	0.71420 (16)	0.74084 (9)	0.0757 (4)
H4A	0.399 (3)	0.659 (3)	0.7402 (16)	0.110 (9)*
N1	0.60064 (15)	0.53308 (13)	0.74272 (8)	0.0469 (3)
N2	0.84324 (17)	0.43573 (14)	0.74782 (9)	0.0459 (3)
H2	0.932 (2)	0.4209 (18)	0.7602 (11)	0.058 (6)*
C1	0.63135 (19)	0.40825 (17)	0.71763 (10)	0.0468 (4)
C2	0.78231 (19)	0.34600 (16)	0.72089 (9)	0.0456 (4)
C3	0.8444 (2)	0.21897 (18)	0.70015 (11)	0.0580 (5)
H3	0.9476	0.1784	0.7024	0.07*
C4	0.7488 (3)	0.1555 (2)	0.67632 (12)	0.0662 (6)
H4	0.7866	0.0684	0.6621	0.079*
C5	0.5980 (3)	0.2156 (2)	0.67245 (12)	0.0682 (6)
H5	0.5356	0.1688	0.6552	0.082*
C6	0.5364 (2)	0.3412 (2)	0.69297 (11)	0.0611 (5)
H6	0.433	0.3809	0.6905	0.073*
C7	0.73012 (18)	0.54517 (15)	0.76063 (9)	0.0410 (4)
C8	0.75575 (18)	0.65893 (15)	0.79120 (9)	0.0403 (4)
C9	0.90130 (19)	0.67082 (17)	0.79719 (11)	0.0506 (4)
H9	0.985	0.6058	0.7793	0.061*
C10	0.92574 (19)	0.77449 (17)	0.82845 (11)	0.0532 (4)
H10	1.0258	0.7811	0.8314	0.064*
C11	0.80424 (18)	0.87005 (16)	0.85584 (10)	0.0443 (4)
C12	0.65882 (18)	0.86278 (16)	0.84867 (10)	0.0466 (4)
H12	0.5757	0.9291	0.8657	0.056*
C13	0.63547 (18)	0.75799 (16)	0.81641 (10)	0.0451 (4)
H13	0.5357	0.7536	0.8114	0.054*
C14	0.72612 (19)	1.07094 (16)	0.91674 (11)	0.0475 (4)
H14A	0.6514	1.0292	0.9626	0.057*
H14B	0.6731	1.1289	0.8692	0.057*
C15	0.8051 (2)	1.15647 (17)	0.94888 (11)	0.0509 (4)
H15A	0.8865	1.1883	0.9038	0.061*
H15B	0.8527	1.0971	0.9981	0.061*
C16	0.70180 (19)	1.28240 (16)	0.97557 (11)	0.0470 (4)
H16A	0.659	1.3453	0.9257	0.056*
H16B	0.6171	1.2518	1.0185	0.056*
C17	0.7843 (2)	1.36046 (18)	1.01216 (13)	0.0608 (5)
H17A	0.8229	1.2974	1.0633	0.073*
H17B	0.8729	1.3846	0.9701	0.073*
C18	0.69371 (19)	1.49118 (16)	1.03617 (10)	0.0473 (4)
H18A	0.6012	1.4692	1.0751	0.057*
H18B	0.6622	1.5581	0.9844	0.057*
C19	0.7784 (2)	1.55899 (18)	1.07856 (13)	0.0567 (5)
H19A	0.8018	1.4951	1.1329	0.068*
H19B	0.8754	1.5729	1.0419	0.068*
C20	0.6945 (2)	1.69577 (17)	1.09593 (11)	0.0521 (4)
H20A	0.683	1.7629	1.0409	0.062*
H20B	0.5921	1.6842	1.1258	0.062*
C21	0.76678 (18)	1.75583 (16)	1.14742 (10)	0.0447 (4)
C22	0.7634 (2)	1.9581 (2)	1.19342 (14)	0.0723 (6)
H22A	0.8706	1.9604	1.1729	0.108*
H22B	0.7511	1.9071	1.2529	0.108*
H22C	0.7067	2.0529	1.1887	0.108*
C23	0.2834 (5)	0.7949 (5)	0.6597 (3)	0.0857 (13)	0.891 (7)
H23A	0.3517	0.863	0.6429	0.103*	0.891 (7)
H23B	0.1784	0.8472	0.6615	0.103*	0.891 (7)
C24	0.3137 (5)	0.7109 (3)	0.59272 (16)	0.0823 (11)	0.891 (7)
H24A	0.3033	0.7757	0.5368	0.099*	0.891 (7)
H24B	0.4196	0.661	0.5901	0.099*	0.891 (7)
C25	0.2134 (4)	0.6076 (3)	0.6065 (3)	0.0744 (10)	0.891 (7)
H25A	0.2207	0.545	0.6633	0.089*	0.891 (7)
H25B	0.1078	0.6579	0.6067	0.089*	0.891 (7)
C33	0.323 (4)	0.788 (5)	0.640 (3)	0.0857 (13)	0.109 (7)
H33A	0.3191	0.889	0.6313	0.103*	0.109 (7)
H33B	0.421	0.748	0.6106	0.103*	0.109 (7)
C34	0.195 (4)	0.763 (2)	0.6059 (16)	0.083 (9)	0.109 (7)
H34A	0.1017	0.819	0.6303	0.1*	0.109 (7)
H34B	0.2093	0.8038	0.544	0.1*	0.109 (7)
C35	0.163 (4)	0.624 (3)	0.617 (3)	0.0744 (10)	0.109 (7)
H35A	0.0519	0.6343	0.6215	0.089*	0.109 (7)
H35B	0.1895	0.5696	0.6734	0.089*	0.109 (7)
C26	0.2471 (3)	0.5223 (3)	0.54287 (13)	0.0858 (7)
H26A	0.2175	0.5828	0.4888	0.103*
H26B	0.3578	0.4906	0.5329	0.103*
C27	0.1752 (3)	0.4003 (2)	0.56313 (14)	0.0869 (7)
H27A	0.2002	0.3402	0.6183	0.104*
H27B	0.0642	0.4307	0.569	0.104*
C28	0.2243 (13)	0.3201 (11)	0.4975 (5)	0.083 (2)	0.638 (13)
H28A	0.3357	0.2948	0.49	0.099*	0.638 (13)
H28B	0.1955	0.3802	0.4432	0.099*	0.638 (13)
C29	0.1581 (10)	0.1850 (5)	0.5163 (2)	0.087 (2)	0.638 (13)
H29A	0.19	0.1238	0.5697	0.104*	0.638 (13)
H29B	0.0467	0.2102	0.5262	0.104*	0.638 (13)
C30	0.2015 (13)	0.1055 (8)	0.4501 (5)	0.121 (3)	0.638 (13)
H30A	0.3102	0.0686	0.445	0.181*	0.638 (13)
H30B	0.1773	0.1662	0.3957	0.181*	0.638 (13)
H30C	0.146	0.0289	0.4655	0.181*	0.638 (13)
C38	0.195 (3)	0.303 (3)	0.4942 (15)	0.160 (12)	0.362 (13)
H38A	0.0954	0.2849	0.4918	0.192*	0.362 (13)
H38B	0.2337	0.3552	0.4371	0.192*	0.362 (13)
C39	0.282 (3)	0.1926 (14)	0.5123 (7)	0.142 (6)	0.362 (13)
H39A	0.2405	0.1381	0.5678	0.17*	0.362 (13)
H39B	0.3802	0.2107	0.518	0.17*	0.362 (13)
C40	0.308 (2)	0.1051 (15)	0.4433 (10)	0.132 (5)	0.362 (13)
H40A	0.2462	0.0328	0.4632	0.199*	0.362 (13)
H40B	0.4146	0.0623	0.4339	0.199*	0.362 (13)
H40C	0.2786	0.1659	0.39	0.199*	0.362 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0460 (7)	0.0514 (7)	0.0809 (8)	−0.0002 (5)	−0.0155 (6)	−0.0336 (6)
O2	0.0633 (8)	0.0470 (7)	0.0772 (8)	−0.0002 (6)	−0.0255 (7)	−0.0252 (6)
O3	0.0554 (8)	0.0570 (7)	0.0766 (8)	−0.0007 (6)	−0.0278 (7)	−0.0223 (6)
O4	0.0621 (10)	0.0867 (10)	0.0775 (10)	0.0025 (8)	−0.0151 (8)	−0.0280 (8)
N1	0.0427 (8)	0.0496 (8)	0.0501 (8)	−0.0063 (6)	−0.0092 (6)	−0.0148 (6)
N2	0.0408 (9)	0.0464 (8)	0.0512 (8)	0.0005 (6)	−0.0109 (7)	−0.0167 (6)
C1	0.0502 (10)	0.0494 (10)	0.0417 (8)	−0.0104 (8)	−0.0067 (7)	−0.0110 (7)
C2	0.0541 (11)	0.0441 (9)	0.0392 (8)	−0.0097 (8)	−0.0066 (7)	−0.0103 (7)
C3	0.0677 (13)	0.0492 (10)	0.0563 (10)	−0.0017 (9)	−0.0080 (9)	−0.0196 (8)
C4	0.0936 (17)	0.0520 (11)	0.0575 (11)	−0.0168 (11)	−0.0074 (11)	−0.0202 (9)
C5	0.0877 (16)	0.0669 (13)	0.0629 (12)	−0.0330 (12)	−0.0119 (11)	−0.0206 (10)
C6	0.0614 (12)	0.0671 (12)	0.0622 (11)	−0.0211 (10)	−0.0129 (9)	−0.0170 (9)
C7	0.0419 (9)	0.0417 (8)	0.0368 (8)	−0.0019 (7)	−0.0059 (7)	−0.0092 (6)
C8	0.0411 (9)	0.0413 (8)	0.0374 (8)	−0.0031 (7)	−0.0076 (7)	−0.0099 (7)
C9	0.0400 (10)	0.0536 (10)	0.0619 (10)	0.0040 (8)	−0.0116 (8)	−0.0276 (8)
C10	0.0379 (9)	0.0576 (10)	0.0702 (11)	−0.0001 (8)	−0.0153 (8)	−0.0270 (9)
C11	0.0445 (10)	0.0418 (9)	0.0482 (9)	−0.0038 (7)	−0.0106 (7)	−0.0137 (7)
C12	0.0365 (9)	0.0440 (9)	0.0585 (10)	−0.0009 (7)	−0.0036 (7)	−0.0185 (8)
C13	0.0364 (9)	0.0454 (9)	0.0547 (9)	−0.0050 (7)	−0.0074 (7)	−0.0151 (7)
C14	0.0454 (10)	0.0423 (9)	0.0550 (10)	−0.0031 (7)	−0.0055 (8)	−0.0176 (7)
C15	0.0496 (10)	0.0466 (9)	0.0602 (10)	−0.0056 (8)	−0.0127 (8)	−0.0182 (8)
C16	0.0448 (10)	0.0460 (9)	0.0527 (9)	−0.0072 (7)	−0.0075 (7)	−0.0163 (7)
C17	0.0507 (11)	0.0544 (10)	0.0886 (13)	−0.0015 (8)	−0.0234 (10)	−0.0330 (10)
C18	0.0450 (10)	0.0474 (9)	0.0523 (9)	−0.0069 (8)	−0.0112 (8)	−0.0150 (7)
C19	0.0440 (10)	0.0532 (10)	0.0822 (13)	−0.0043 (8)	−0.0151 (9)	−0.0309 (9)
C20	0.0523 (11)	0.0517 (10)	0.0559 (10)	−0.0031 (8)	−0.0176 (8)	−0.0173 (8)
C21	0.0407 (9)	0.0437 (9)	0.0493 (9)	−0.0056 (7)	−0.0050 (7)	−0.0133 (7)
C22	0.0754 (15)	0.0601 (12)	0.0967 (15)	−0.0089 (10)	−0.0220 (12)	−0.0401 (11)
C23	0.096 (3)	0.0718 (16)	0.087 (3)	−0.013 (2)	−0.020 (2)	−0.0117 (18)
C24	0.095 (3)	0.083 (2)	0.0648 (15)	−0.0264 (19)	−0.0137 (15)	−0.0020 (13)
C25	0.075 (3)	0.0791 (16)	0.0644 (18)	−0.0075 (17)	−0.0106 (19)	−0.0145 (12)
C33	0.096 (3)	0.0718 (16)	0.087 (3)	−0.013 (2)	−0.020 (2)	−0.0117 (18)
C34	0.09 (2)	0.064 (14)	0.094 (16)	−0.015 (13)	−0.042 (15)	0.009 (11)
C35	0.075 (3)	0.0791 (16)	0.0644 (18)	−0.0075 (17)	−0.0106 (19)	−0.0145 (12)
C26	0.0922 (18)	0.1069 (19)	0.0600 (13)	−0.0280 (15)	−0.0104 (12)	−0.0150 (12)
C27	0.109 (2)	0.0861 (16)	0.0642 (13)	−0.0131 (14)	−0.0149 (13)	−0.0181 (12)
C28	0.114 (4)	0.077 (4)	0.054 (3)	−0.013 (3)	−0.002 (3)	−0.021 (3)
C29	0.123 (5)	0.070 (3)	0.066 (2)	−0.012 (3)	−0.011 (3)	−0.0196 (19)
C30	0.173 (8)	0.093 (3)	0.094 (4)	−0.010 (5)	−0.006 (5)	−0.041 (3)
C38	0.21 (2)	0.14 (2)	0.149 (14)	−0.011 (16)	−0.088 (14)	−0.042 (12)
C39	0.170 (16)	0.125 (10)	0.122 (8)	−0.030 (9)	−0.038 (9)	0.000 (7)
C40	0.180 (14)	0.101 (7)	0.113 (7)	−0.013 (10)	0.008 (11)	−0.052 (6)

Geometric parameters (Å, º)

O1—C11	1.3639 (19)	C19—H19B	0.99
O1—C14	1.4390 (19)	C20—C21	1.494 (2)
O2—C21	1.3423 (19)	C20—H20A	0.99
O2—C22	1.447 (2)	C20—H20B	0.99
O3—C21	1.2074 (19)	C22—H22A	0.98
O4—C23	1.397 (5)	C22—H22B	0.98
O4—C33	1.63 (5)	C22—H22C	0.98
O4—H4A	0.93 (3)	C23—C24	1.522 (5)
N1—C7	1.323 (2)	C23—H23A	0.99
N1—C1	1.395 (2)	C23—H23B	0.99
N2—C7	1.373 (2)	C24—C25	1.498 (4)
N2—C2	1.379 (2)	C24—H24A	0.99
N2—H2	0.852 (19)	C24—H24B	0.99
C1—C2	1.395 (2)	C25—C26	1.482 (4)
C1—C6	1.401 (2)	C25—H25A	0.99
C2—C3	1.395 (2)	C25—H25B	0.99
C3—C4	1.372 (3)	C33—C34	1.502 (19)
C3—H3	0.95	C33—H33A	0.99
C4—C5	1.391 (3)	C33—H33B	0.99
C4—H4	0.95	C34—C35	1.470 (18)
C5—C6	1.380 (3)	C34—H34A	0.99
C5—H5	0.95	C34—H34B	0.99
C6—H6	0.95	C35—C26	1.77 (3)
C7—C8	1.464 (2)	C35—H35A	0.99
C8—C13	1.397 (2)	C35—H35B	0.99
C8—C9	1.397 (2)	C26—C27	1.472 (3)
C9—C10	1.372 (2)	C26—H26A	0.99
C9—H9	0.95	C26—H26B	0.99
C10—C11	1.394 (2)	C27—C28	1.469 (10)
C10—H10	0.95	C27—C38	1.66 (3)
C11—C12	1.387 (2)	C27—H27A	0.99
C12—C13	1.389 (2)	C27—H27B	0.99
C12—H12	0.95	C28—C29	1.563 (15)
C13—H13	0.95	C28—H28A	0.99
C14—C15	1.504 (2)	C28—H28B	0.99
C14—H14A	0.99	C29—C30	1.473 (8)
C14—H14B	0.99	C29—H29A	0.99
C15—C16	1.526 (2)	C29—H29B	0.99
C15—H15A	0.99	C30—H30A	0.98
C15—H15B	0.99	C30—H30B	0.98
C16—C17	1.514 (2)	C30—H30C	0.98
C16—H16A	0.99	C38—C39	1.23 (3)
C16—H16B	0.99	C38—H38A	0.99
C17—C18	1.509 (2)	C38—H38B	0.99
C17—H17A	0.99	C39—C40	1.579 (18)
C17—H17B	0.99	C39—H39A	0.99
C18—C19	1.516 (2)	C39—H39B	0.99
C18—H18A	0.99	C40—H40A	0.98
C18—H18B	0.99	C40—H40B	0.98
C19—C20	1.504 (2)	C40—H40C	0.98
C19—H19A	0.99
C11—O1—C14	119.68 (13)	O2—C22—H22A	109.5
C21—O2—C22	116.64 (14)	O2—C22—H22B	109.5
C23—O4—H4A	110.8 (16)	H22A—C22—H22B	109.5
C33—O4—H4A	96 (2)	O2—C22—H22C	109.5
C7—N1—C1	104.99 (13)	H22A—C22—H22C	109.5
C7—N2—C2	107.65 (14)	H22B—C22—H22C	109.5
C7—N2—H2	126.0 (12)	O4—C23—C24	113.4 (4)
C2—N2—H2	125.9 (12)	O4—C23—H23A	108.9
N1—C1—C2	110.31 (14)	C24—C23—H23A	108.9
N1—C1—C6	130.43 (16)	O4—C23—H23B	108.9
C2—C1—C6	119.25 (16)	C24—C23—H23B	108.9
N2—C2—C3	132.15 (17)	H23A—C23—H23B	107.7
N2—C2—C1	104.98 (14)	C25—C24—C23	115.6 (3)
C3—C2—C1	122.87 (16)	C25—C24—H24A	108.4
C4—C3—C2	116.66 (18)	C23—C24—H24A	108.4
C4—C3—H3	121.7	C25—C24—H24B	108.4
C2—C3—H3	121.7	C23—C24—H24B	108.4
C3—C4—C5	121.54 (18)	H24A—C24—H24B	107.4
C3—C4—H4	119.2	C26—C25—C24	115.4 (3)
C5—C4—H4	119.2	C26—C25—H25A	108.4
C6—C5—C4	121.88 (18)	C24—C25—H25A	108.4
C6—C5—H5	119.1	C26—C25—H25B	108.4
C4—C5—H5	119.1	C24—C25—H25B	108.4
C5—C6—C1	117.79 (19)	H25A—C25—H25B	107.5
C5—C6—H6	121.1	C34—C33—O4	106 (3)
C1—C6—H6	121.1	C34—C33—H33A	110.5
N1—C7—N2	112.07 (14)	O4—C33—H33A	110.5
N1—C7—C8	125.98 (14)	C34—C33—H33B	110.5
N2—C7—C8	121.95 (14)	O4—C33—H33B	110.5
C13—C8—C9	117.82 (15)	H33A—C33—H33B	108.6
C13—C8—C7	121.15 (15)	C35—C34—C33	123 (2)
C9—C8—C7	121.02 (14)	C35—C34—H34A	106.7
C10—C9—C8	121.33 (15)	C33—C34—H34A	106.7
C10—C9—H9	119.3	C35—C34—H34B	106.7
C8—C9—H9	119.3	C33—C34—H34B	106.7
C9—C10—C11	120.19 (16)	H34A—C34—H34B	106.6
C9—C10—H10	119.9	C34—C35—C26	121 (3)
C11—C10—H10	119.9	C34—C35—H35A	107.1
O1—C11—C12	125.45 (15)	C26—C35—H35A	107.1
O1—C11—C10	114.85 (14)	C34—C35—H35B	107.1
C12—C11—C10	119.69 (15)	C26—C35—H35B	107.1
C11—C12—C13	119.60 (15)	H35A—C35—H35B	106.8
C11—C12—H12	120.2	C27—C26—C25	117.3 (2)
C13—C12—H12	120.2	C27—C26—C35	108.7 (9)
C12—C13—C8	121.31 (15)	C27—C26—H26A	108.0
C12—C13—H13	119.3	C25—C26—H26A	108.0
C8—C13—H13	119.3	C27—C26—H26B	108.0
O1—C14—C15	106.08 (13)	C25—C26—H26B	108.0
O1—C14—H14A	110.5	H26A—C26—H26B	107.2
C15—C14—H14A	110.5	C28—C27—C26	112.1 (5)
O1—C14—H14B	110.5	C26—C27—C38	121.6 (10)
C15—C14—H14B	110.5	C28—C27—H27A	109.2
H14A—C14—H14B	108.7	C26—C27—H27A	109.2
C14—C15—C16	114.12 (14)	C28—C27—H27B	109.2
C14—C15—H15A	108.7	C26—C27—H27B	109.2
C16—C15—H15A	108.7	H27A—C27—H27B	107.9
C14—C15—H15B	108.7	C27—C28—C29	115.2 (5)
C16—C15—H15B	108.7	C27—C28—H28A	108.5
H15A—C15—H15B	107.6	C29—C28—H28A	108.5
C17—C16—C15	112.17 (14)	C27—C28—H28B	108.5
C17—C16—H16A	109.2	C29—C28—H28B	108.5
C15—C16—H16A	109.2	H28A—C28—H28B	107.5
C17—C16—H16B	109.2	C30—C29—C28	116.2 (5)
C15—C16—H16B	109.2	C30—C29—H29A	108.2
H16A—C16—H16B	107.9	C28—C29—H29A	108.2
C18—C17—C16	116.17 (15)	C30—C29—H29B	108.2
C18—C17—H17A	108.2	C28—C29—H29B	108.2
C16—C17—H17A	108.2	H29A—C29—H29B	107.4
C18—C17—H17B	108.2	C29—C30—H30A	109.5
C16—C17—H17B	108.2	C29—C30—H30B	109.5
H17A—C17—H17B	107.4	H30A—C30—H30B	109.5
C17—C18—C19	113.83 (14)	C29—C30—H30C	109.5
C17—C18—H18A	108.8	H30A—C30—H30C	109.5
C19—C18—H18A	108.8	H30B—C30—H30C	109.5
C17—C18—H18B	108.8	C39—C38—C27	113 (2)
C19—C18—H18B	108.8	C39—C38—H38A	109.0
H18A—C18—H18B	107.7	C27—C38—H38A	109.0
C20—C19—C18	114.43 (14)	C39—C38—H38B	109.0
C20—C19—H19A	108.7	C27—C38—H38B	109.0
C18—C19—H19A	108.7	H38A—C38—H38B	107.8
C20—C19—H19B	108.7	C38—C39—C40	112.5 (17)
C18—C19—H19B	108.7	C38—C39—H39A	109.1
H19A—C19—H19B	107.6	C40—C39—H39A	109.1
C21—C20—C19	115.35 (14)	C38—C39—H39B	109.1
C21—C20—H20A	108.4	C40—C39—H39B	109.1
C19—C20—H20A	108.4	H39A—C39—H39B	107.8
C21—C20—H20B	108.4	C39—C40—H40A	109.5
C19—C20—H20B	108.4	C39—C40—H40B	109.5
H20A—C20—H20B	107.5	H40A—C40—H40B	109.5
O3—C21—O2	122.44 (15)	C39—C40—H40C	109.5
O3—C21—C20	125.97 (15)	H40A—C40—H40C	109.5
O2—C21—C20	111.57 (14)	H40B—C40—H40C	109.5
C7—N1—C1—C2	−0.04 (17)	C9—C10—C11—C12	−2.2 (3)
C7—N1—C1—C6	178.66 (16)	O1—C11—C12—C13	−177.98 (14)
C7—N2—C2—C3	−178.86 (17)	C10—C11—C12—C13	1.8 (2)
C7—N2—C2—C1	0.74 (17)	C11—C12—C13—C8	0.3 (2)
N1—C1—C2—N2	−0.44 (17)	C9—C8—C13—C12	−1.8 (2)
C6—C1—C2—N2	−179.31 (14)	C7—C8—C13—C12	177.35 (14)
N1—C1—C2—C3	179.21 (14)	C11—O1—C14—C15	179.93 (13)
C6—C1—C2—C3	0.3 (2)	O1—C14—C15—C16	175.52 (13)
N2—C2—C3—C4	179.13 (16)	C14—C15—C16—C17	176.69 (15)
C1—C2—C3—C4	−0.4 (2)	C15—C16—C17—C18	176.87 (15)
C2—C3—C4—C5	0.5 (3)	C16—C17—C18—C19	175.59 (16)
C3—C4—C5—C6	−0.6 (3)	C17—C18—C19—C20	174.91 (16)
C4—C5—C6—C1	0.5 (3)	C18—C19—C20—C21	172.52 (15)
N1—C1—C6—C5	−178.96 (16)	C22—O2—C21—O3	−1.2 (3)
C2—C1—C6—C5	−0.3 (2)	C22—O2—C21—C20	177.23 (15)
C1—N1—C7—N2	0.53 (17)	C19—C20—C21—O3	−16.7 (3)
C1—N1—C7—C8	−179.08 (14)	C19—C20—C21—O2	164.90 (15)
C2—N2—C7—N1	−0.83 (18)	O4—C23—C24—C25	61.7 (5)
C2—N2—C7—C8	178.80 (13)	C23—C24—C25—C26	−177.8 (4)
N1—C7—C8—C13	9.6 (2)	O4—C33—C34—C35	−54 (5)
N2—C7—C8—C13	−169.95 (14)	C33—C34—C35—C26	−89 (5)
N1—C7—C8—C9	−171.26 (15)	C24—C25—C26—C27	167.0 (3)
N2—C7—C8—C9	9.2 (2)	C34—C35—C26—C27	−171 (2)
C13—C8—C9—C10	1.3 (2)	C25—C26—C27—C28	−176.7 (5)
C7—C8—C9—C10	−177.79 (15)	C35—C26—C27—C38	164.7 (18)
C8—C9—C10—C11	0.6 (3)	C26—C27—C28—C29	177.4 (6)
C14—O1—C11—C12	−2.0 (2)	C27—C28—C29—C30	177.9 (7)
C14—O1—C11—C10	178.29 (14)	C26—C27—C38—C39	105 (2)
C9—C10—C11—O1	177.56 (15)	C27—C38—C39—C40	−176.6 (12)

Hydrogen-bond geometry (Å, º)

Cg(X) refers to ring centroids, where Bz and Im are the benzene and imidazole rings of the benzimidiazole unit, respectively, and Ph is the phenylene substituent.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···N1	0.93 (3)	2.01 (3)	2.932 (2)	178 (2)
N2—H2···O3^i	0.852 (19)	2.161 (19)	2.968 (2)	158.1 (16)
C14—H14B···Cg(Bz)^ii	0.99	2.85	3.731 (2)	149
C16—H16A···Cg(Im)^ii	0.99	2.99	3.837 (2)	145
C18—H18B···Cg(Ph)^ii	0.99	3.11	3.9394 (18)	143

Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) x, y+1, z.