1-Benzyl-2-[2-(benz­yloxy)phen­yl]-1H-benzimidazole

The title compound, C₂₇H₂₂N₂O, was prepared by reaction of 2-(2-hydroxy­phen­yl)benzimidazole with chloro­methyl­benzene under reflux. The large steric effect of the benzyl substituents results in the phenolate rings and benzimidazole rings being non-coplanar. This is responsible for the observed weak photoluminescence. The crystal structure is determined by inter­molecular van der Waals inter­actions. No hydrogen-bond inter­actions or π–π stacking inter­actions were found, which is somewhat unusual for an aromatic heterocyclic compound.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.045
• wR factor = 0.110
• Data-to-parameter ratio = 8.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.64 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.00
           From the CIF: _reflns_number_total               2400
           Count of symmetry unique reflns         2405
           Completeness (_total/calc)             99.79%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXL97.

1-Benzyl-2-[2-(benzyloxy)phenyl]-1H-benzimidazole

Crystal data

C27H22N2O	F(000) = 824
Mr = 390.47	Dx = 1.228 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2398 reflections
a = 10.2724 (9) Å	θ = 2.4–20.4°
b = 15.8390 (13) Å	µ = 0.08 mm^−1
c = 12.9779 (11) Å	T = 293 K
V = 2111.6 (3) Å^3	Block, colorless
Z = 4	0.53 × 0.33 × 0.28 mm

Data collection

Bruker APEX area-detector diffractometer	2400 independent reflections
Radiation source: fine-focus sealed tube	2048 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
Tmin = 0.961, Tmax = 0.979	k = −20→10
11837 measured reflections	l = −16→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0548P)^2 + 0.1914P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
2400 reflections	Δρmax = 0.16 e Å^−3
271 parameters	Δρmin = −0.13 e Å^−3
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods

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
O1	0.31914 (17)	0.20469 (12)	0.74398 (18)	0.0595 (5)
N1	0.42036 (19)	0.02756 (13)	0.73542 (16)	0.0441 (5)
N2	0.4892 (2)	0.06866 (15)	0.57967 (17)	0.0476 (5)
C1	0.2294 (2)	0.17863 (17)	0.6738 (2)	0.0477 (6)
C2	0.1143 (3)	0.22025 (19)	0.6510 (3)	0.0599 (8)
H2	0.0931	0.2702	0.6847	0.072*
C3	0.0319 (3)	0.1870 (2)	0.5784 (3)	0.0651 (8)
H3	−0.0457	0.2148	0.5635	0.078*
C4	0.0614 (3)	0.1140 (2)	0.5275 (2)	0.0650 (8)
H4	0.0042	0.0923	0.4788	0.078*
C5	0.1773 (3)	0.0725 (2)	0.5490 (2)	0.0536 (7)
H5	0.1980	0.0230	0.5140	0.064*
C6	0.2619 (2)	0.10418 (16)	0.6221 (2)	0.0441 (6)
C7	0.3909 (2)	0.06495 (15)	0.64357 (19)	0.0417 (5)
C8	0.5920 (2)	0.03244 (15)	0.6335 (2)	0.0434 (5)
C9	0.7226 (2)	0.02415 (19)	0.6064 (2)	0.0545 (7)
H9	0.7528	0.0425	0.5426	0.065*
C10	0.8051 (3)	−0.0120 (2)	0.6768 (2)	0.0589 (7)
H10	0.8925	−0.0186	0.6599	0.071*
C11	0.7616 (3)	−0.03901 (18)	0.7731 (2)	0.0583 (7)
H11	0.8205	−0.0637	0.8184	0.070*
C12	0.6331 (3)	−0.03019 (17)	0.8030 (2)	0.0521 (6)
H12	0.6039	−0.0477	0.8674	0.063*
C13	0.5502 (2)	0.00630 (14)	0.7311 (2)	0.0419 (5)
C14	0.2688 (2)	−0.07627 (16)	0.8141 (2)	0.0448 (6)
C15	0.1561 (3)	−0.0857 (2)	0.7603 (3)	0.0726 (9)
H15	0.1190	−0.0392	0.7279	0.087*
C16	0.0962 (4)	−0.1635 (2)	0.7531 (4)	0.0907 (13)
H16	0.0194	−0.1690	0.7157	0.109*
C17	0.1488 (4)	−0.2319 (2)	0.8003 (4)	0.0861 (11)
H17	0.1095	−0.2845	0.7937	0.103*
C18	0.2592 (4)	−0.2232 (2)	0.8574 (4)	0.0819 (11)
H18	0.2944	−0.2697	0.8910	0.098*
C19	0.3190 (3)	−0.14526 (18)	0.8653 (3)	0.0604 (8)
H19	0.3935	−0.1393	0.9054	0.072*
C20	0.4008 (3)	0.2843 (2)	0.8816 (3)	0.0637 (8)
C21	0.4340 (4)	0.2161 (2)	0.9427 (3)	0.0815 (10)
H21	0.3893	0.1654	0.9349	0.098*
C22	0.5324 (4)	0.2217 (3)	1.0150 (4)	0.0997 (13)
H22	0.5530	0.1754	1.0558	0.120*
C23	0.5999 (4)	0.2967 (4)	1.0263 (4)	0.1038 (16)
H23	0.6668	0.3011	1.0743	0.125*
C24	0.5678 (5)	0.3634 (4)	0.9669 (4)	0.1100 (18)
H24	0.6131	0.4138	0.9745	0.132*
C25	0.4700 (4)	0.3585 (2)	0.8957 (3)	0.0851 (12)
H25	0.4496	0.4056	0.8561	0.102*
C26	0.3329 (3)	0.00919 (17)	0.8218 (2)	0.0483 (6)
H26A	0.2659	0.0523	0.8247	0.058*
H26B	0.3820	0.0120	0.8856	0.058*
C27	0.2953 (3)	0.27833 (19)	0.8043 (3)	0.0653 (8)
H27A	0.2115	0.2741	0.8383	0.078*
H27B	0.2950	0.3281	0.7607	0.078*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0507 (10)	0.0538 (11)	0.0741 (14)	0.0051 (8)	−0.0043 (10)	−0.0136 (10)
N1	0.0430 (11)	0.0476 (12)	0.0418 (11)	0.0000 (9)	0.0054 (9)	0.0045 (9)
N2	0.0423 (11)	0.0574 (13)	0.0430 (12)	0.0029 (9)	0.0040 (9)	−0.0003 (10)
C1	0.0422 (13)	0.0511 (15)	0.0498 (15)	−0.0028 (11)	0.0044 (12)	0.0060 (12)
C2	0.0517 (15)	0.0619 (17)	0.066 (2)	0.0107 (13)	0.0095 (14)	0.0089 (15)
C3	0.0439 (15)	0.091 (2)	0.0599 (19)	0.0144 (15)	0.0026 (14)	0.0101 (18)
C4	0.0430 (15)	0.098 (2)	0.0543 (18)	−0.0055 (15)	−0.0043 (13)	0.0044 (17)
C5	0.0493 (15)	0.0681 (18)	0.0433 (14)	−0.0036 (13)	0.0042 (12)	−0.0018 (13)
C6	0.0388 (12)	0.0515 (14)	0.0420 (13)	−0.0009 (10)	0.0059 (11)	0.0054 (12)
C7	0.0450 (13)	0.0434 (13)	0.0365 (12)	−0.0037 (10)	0.0024 (11)	−0.0025 (11)
C8	0.0414 (12)	0.0471 (14)	0.0415 (13)	0.0030 (10)	0.0013 (11)	−0.0051 (12)
C9	0.0479 (14)	0.0732 (19)	0.0423 (15)	0.0057 (13)	0.0044 (12)	−0.0019 (13)
C10	0.0444 (14)	0.0752 (19)	0.0570 (18)	0.0090 (13)	0.0036 (13)	−0.0078 (15)
C11	0.0543 (16)	0.0620 (17)	0.0587 (17)	0.0122 (13)	−0.0091 (14)	0.0025 (14)
C12	0.0573 (15)	0.0538 (16)	0.0452 (15)	0.0013 (13)	−0.0015 (13)	0.0053 (12)
C13	0.0426 (12)	0.0396 (12)	0.0435 (13)	−0.0004 (10)	0.0009 (11)	−0.0032 (11)
C14	0.0414 (13)	0.0494 (14)	0.0437 (14)	0.0008 (10)	0.0038 (11)	0.0032 (11)
C15	0.0651 (18)	0.071 (2)	0.081 (2)	−0.0081 (15)	−0.0186 (17)	0.0248 (18)
C16	0.079 (2)	0.084 (2)	0.108 (3)	−0.0255 (19)	−0.044 (2)	0.017 (2)
C17	0.083 (2)	0.058 (2)	0.117 (3)	−0.0172 (18)	−0.016 (3)	−0.002 (2)
C18	0.081 (2)	0.0506 (18)	0.114 (3)	0.0027 (16)	−0.020 (2)	0.0137 (19)
C19	0.0546 (15)	0.0569 (17)	0.070 (2)	0.0018 (13)	−0.0137 (15)	0.0064 (15)
C20	0.0674 (18)	0.0593 (17)	0.0643 (19)	−0.0070 (15)	0.0112 (15)	−0.0144 (16)
C21	0.084 (2)	0.075 (2)	0.086 (3)	−0.0066 (19)	−0.013 (2)	−0.015 (2)
C22	0.098 (3)	0.120 (4)	0.081 (3)	0.003 (3)	−0.012 (2)	−0.016 (3)
C23	0.074 (2)	0.169 (5)	0.068 (3)	−0.025 (3)	0.003 (2)	−0.044 (3)
C24	0.112 (4)	0.138 (5)	0.080 (3)	−0.060 (3)	0.025 (3)	−0.047 (3)
C25	0.105 (3)	0.079 (2)	0.072 (2)	−0.024 (2)	0.020 (2)	−0.025 (2)
C26	0.0516 (14)	0.0515 (15)	0.0418 (14)	−0.0006 (11)	0.0100 (12)	0.0028 (12)
C27	0.0706 (18)	0.0500 (16)	0.075 (2)	0.0024 (14)	0.0070 (18)	−0.0084 (15)

Geometric parameters (Å, º)

O1—C1	1.361 (3)	C14—C15	1.360 (4)
O1—C27	1.426 (3)	C14—C19	1.379 (4)
N1—C7	1.365 (3)	C14—C26	1.509 (4)
N1—C13	1.377 (3)	C15—C16	1.380 (5)
N1—C26	1.466 (3)	C15—H15	0.9300
N2—C7	1.308 (3)	C16—C17	1.357 (5)
N2—C8	1.391 (3)	C16—H16	0.9300
C1—C2	1.385 (4)	C17—C18	1.362 (5)
C1—C6	1.397 (4)	C17—H17	0.9300
C2—C3	1.372 (4)	C18—C19	1.383 (5)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.365 (5)	C19—H19	0.9300
C3—H3	0.9300	C20—C21	1.383 (5)
C4—C5	1.389 (4)	C20—C25	1.385 (5)
C4—H4	0.9300	C20—C27	1.480 (5)
C5—C6	1.381 (4)	C21—C22	1.382 (6)
C5—H5	0.9300	C21—H21	0.9300
C6—C7	1.490 (3)	C22—C23	1.384 (7)
C8—C9	1.393 (3)	C22—H22	0.9300
C8—C13	1.400 (4)	C23—C24	1.348 (7)
C9—C10	1.372 (4)	C23—H23	0.9300
C9—H9	0.9300	C24—C25	1.367 (7)
C10—C11	1.395 (4)	C24—H24	0.9300
C10—H10	0.9300	C25—H25	0.9300
C11—C12	1.383 (4)	C26—H26A	0.9700
C11—H11	0.9300	C26—H26B	0.9700
C12—C13	1.388 (4)	C27—H27A	0.9700
C12—H12	0.9300	C27—H27B	0.9700
C1—O1—C27	120.0 (2)	C19—C14—C26	121.0 (2)
C7—N1—C13	106.6 (2)	C14—C15—C16	120.9 (3)
C7—N1—C26	128.2 (2)	C14—C15—H15	119.6
C13—N1—C26	125.2 (2)	C16—C15—H15	119.6
C7—N2—C8	104.4 (2)	C17—C16—C15	120.3 (3)
O1—C1—C2	125.2 (3)	C17—C16—H16	119.9
O1—C1—C6	114.5 (2)	C15—C16—H16	119.9
C2—C1—C6	120.2 (2)	C16—C17—C18	119.8 (3)
C3—C2—C1	119.4 (3)	C16—C17—H17	120.1
C3—C2—H2	120.3	C18—C17—H17	120.1
C1—C2—H2	120.3	C17—C18—C19	120.0 (3)
C4—C3—C2	121.3 (3)	C17—C18—H18	120.0
C4—C3—H3	119.3	C19—C18—H18	120.0
C2—C3—H3	119.3	C14—C19—C18	120.4 (3)
C3—C4—C5	119.7 (3)	C14—C19—H19	119.8
C3—C4—H4	120.2	C18—C19—H19	119.8
C5—C4—H4	120.2	C21—C20—C25	117.4 (4)
C6—C5—C4	120.3 (3)	C21—C20—C27	121.3 (3)
C6—C5—H5	119.8	C25—C20—C27	121.3 (3)
C4—C5—H5	119.8	C22—C21—C20	121.3 (4)
C5—C6—C1	119.1 (2)	C22—C21—H21	119.4
C5—C6—C7	122.4 (2)	C20—C21—H21	119.4
C1—C6—C7	118.4 (2)	C21—C22—C23	119.6 (5)
N2—C7—N1	113.7 (2)	C21—C22—H22	120.2
N2—C7—C6	123.3 (2)	C23—C22—H22	120.2
N1—C7—C6	122.8 (2)	C24—C23—C22	119.3 (4)
N2—C8—C9	130.0 (2)	C24—C23—H23	120.4
N2—C8—C13	110.1 (2)	C22—C23—H23	120.4
C9—C8—C13	119.8 (2)	C23—C24—C25	121.5 (4)
C10—C9—C8	117.7 (3)	C23—C24—H24	119.3
C10—C9—H9	121.1	C25—C24—H24	119.3
C8—C9—H9	121.1	C24—C25—C20	121.0 (5)
C9—C10—C11	121.8 (3)	C24—C25—H25	119.5
C9—C10—H10	119.1	C20—C25—H25	119.5
C11—C10—H10	119.1	N1—C26—C14	113.2 (2)
C12—C11—C10	121.8 (3)	N1—C26—H26A	108.9
C12—C11—H11	119.1	C14—C26—H26A	108.9
C10—C11—H11	119.1	N1—C26—H26B	108.9
C11—C12—C13	116.0 (3)	C14—C26—H26B	108.9
C11—C12—H12	122.0	H26A—C26—H26B	107.7
C13—C12—H12	122.0	O1—C27—C20	107.4 (2)
N1—C13—C12	132.0 (2)	O1—C27—H27A	110.2
N1—C13—C8	105.1 (2)	C20—C27—H27A	110.2
C12—C13—C8	122.9 (2)	O1—C27—H27B	110.2
C15—C14—C19	118.6 (3)	C20—C27—H27B	110.2
C15—C14—C26	120.3 (2)	H27A—C27—H27B	108.5
C27—O1—C1—C2	2.9 (4)	C7—N1—C13—C8	−0.5 (2)
C27—O1—C1—C6	−177.9 (3)	C26—N1—C13—C8	177.2 (2)
O1—C1—C2—C3	−179.9 (3)	C11—C12—C13—N1	−177.1 (3)
C6—C1—C2—C3	0.9 (4)	C11—C12—C13—C8	0.5 (4)
C1—C2—C3—C4	−0.4 (5)	N2—C8—C13—N1	−0.2 (3)
C2—C3—C4—C5	−0.3 (5)	C9—C8—C13—N1	176.5 (2)
C3—C4—C5—C6	0.6 (4)	N2—C8—C13—C12	−178.3 (2)
C4—C5—C6—C1	−0.2 (4)	C9—C8—C13—C12	−1.7 (4)
C4—C5—C6—C7	−176.2 (3)	C19—C14—C15—C16	−2.9 (5)
O1—C1—C6—C5	−179.8 (2)	C26—C14—C15—C16	−179.7 (3)
C2—C1—C6—C5	−0.6 (4)	C14—C15—C16—C17	0.3 (7)
O1—C1—C6—C7	−3.6 (3)	C15—C16—C17—C18	1.8 (7)
C2—C1—C6—C7	175.6 (3)	C16—C17—C18—C19	−1.4 (7)
C8—N2—C7—N1	−1.1 (3)	C15—C14—C19—C18	3.3 (5)
C8—N2—C7—C6	174.0 (2)	C26—C14—C19—C18	−179.9 (3)
C13—N1—C7—N2	1.0 (3)	C17—C18—C19—C14	−1.2 (6)
C26—N1—C7—N2	−176.6 (2)	C25—C20—C21—C22	0.0 (5)
C13—N1—C7—C6	−174.1 (2)	C27—C20—C21—C22	−179.9 (3)
C26—N1—C7—C6	8.3 (4)	C20—C21—C22—C23	−0.5 (6)
C5—C6—C7—N2	71.1 (3)	C21—C22—C23—C24	0.5 (7)
C1—C6—C7—N2	−105.0 (3)	C22—C23—C24—C25	−0.1 (7)
C5—C6—C7—N1	−114.2 (3)	C23—C24—C25—C20	−0.4 (6)
C1—C6—C7—N1	69.7 (3)	C21—C20—C25—C24	0.4 (5)
C7—N2—C8—C9	−175.4 (3)	C27—C20—C25—C24	−179.6 (4)
C7—N2—C8—C13	0.7 (3)	C7—N1—C26—C14	89.2 (3)
N2—C8—C9—C10	177.6 (3)	C13—N1—C26—C14	−88.0 (3)
C13—C8—C9—C10	1.7 (4)	C15—C14—C26—N1	−86.5 (3)
C8—C9—C10—C11	−0.6 (4)	C19—C14—C26—N1	96.8 (3)
C9—C10—C11—C12	−0.6 (5)	C1—O1—C27—C20	173.0 (2)
C10—C11—C12—C13	0.6 (4)	C21—C20—C27—O1	−50.1 (4)
C7—N1—C13—C12	177.5 (3)	C25—C20—C27—O1	129.9 (3)
C26—N1—C13—C12	−4.8 (4)