2-(2-Benz­yloxy-3-methoxy­phen­yl)-1H-benzimidazole

In the title mol­ecule, C₂₁H₁₈N₂O₂, all bond lengths and angles are normal. Weak inter­molecular N—H...N hydrogen bonds link the mol­ecules into chains along the c axis. The crystal packing is further stabilized by van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.050
• wR factor = 0.137
• Data-to-parameter ratio = 34.6

checkCIF/PLATON results

No syntax errors found



Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.613
            Test value =      0.600
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.61 mm
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       0.61 e/A   
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?

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

   2 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

2-(2-Benzyloxy-3-methoxyphenyl)-1H-benzimidazole

Crystal data

C21H18N2O2	F(000) = 696
Mr = 330.37	Dx = 1.355 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9799 reflections
a = 9.5417 (1) Å	θ = 2.2–37.5°
b = 18.4590 (3) Å	µ = 0.09 mm^−1
c = 11.0653 (2) Å	T = 100 K
β = 123.814 (1)°	Block, yellow
V = 1619.27 (4) Å^3	0.61 × 0.28 × 0.22 mm
Z = 4

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	8446 independent reflections
Radiation source: fine-focus sealed tube	6691 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
Detector resolution: 8.33 pixels mm^-1	θmax = 37.5°, θmin = 2.2°
ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −30→31
Tmin = 0.893, Tmax = 0.981	l = −18→17
54869 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0705P)^2 + 0.2664P] where P = (Fo^2 + 2Fc^2)/3
8446 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.61 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

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	0.10948 (7)	0.35671 (3)	0.40580 (6)	0.01535 (11)
O2	0.28286 (8)	0.47957 (3)	0.49450 (7)	0.01712 (11)
N1	−0.08358 (8)	0.25757 (4)	0.42611 (7)	0.01520 (12)
H1A	−0.0567	0.2688	0.3661	0.030 (4)*
N2	−0.09743 (8)	0.26345 (4)	0.62225 (7)	0.01523 (12)
C1	−0.18086 (9)	0.19963 (4)	0.41483 (8)	0.01463 (13)
C2	−0.26354 (11)	0.14613 (5)	0.30896 (9)	0.01859 (14)
H2A	−0.2572	0.1441	0.2282	0.034 (4)*
C3	−0.35590 (11)	0.09598 (5)	0.33065 (10)	0.01993 (15)
H3A	−0.4136	0.0595	0.2623	0.027 (3)*
C4	−0.36435 (11)	0.09899 (5)	0.45379 (10)	0.01929 (15)
H4A	−0.4276	0.0645	0.4647	0.029 (3)*
C5	−0.28037 (10)	0.15220 (5)	0.55902 (9)	0.01746 (14)
H5A	−0.2853	0.1535	0.6406	0.025 (3)*
C6	−0.18786 (9)	0.20395 (4)	0.53842 (8)	0.01437 (12)
C7	−0.03755 (9)	0.29411 (4)	0.55100 (8)	0.01380 (12)
C8	0.05824 (9)	0.36220 (4)	0.59596 (8)	0.01368 (12)
C9	0.07150 (10)	0.40165 (4)	0.71080 (8)	0.01595 (13)
H9A	0.0257	0.3830	0.7596	0.021 (3)*
C10	0.15239 (10)	0.46804 (5)	0.75130 (9)	0.01747 (14)
H10A	0.1582	0.4941	0.8259	0.025 (3)*
C11	0.22545 (10)	0.49655 (4)	0.68192 (9)	0.01667 (13)
H11A	0.2804	0.5410	0.7107	0.023 (3)*
C12	0.21538 (9)	0.45794 (4)	0.56944 (8)	0.01443 (12)
C13	0.12986 (9)	0.39098 (4)	0.52534 (8)	0.01360 (12)
C14	0.25974 (10)	0.32282 (5)	0.43057 (9)	0.01732 (14)
H14A	0.2528	0.2709	0.4395	0.023 (3)*
H14B	0.3574	0.3405	0.5212	0.019 (3)*
C15	0.28144 (9)	0.33836 (4)	0.30860 (8)	0.01454 (12)
C16	0.40292 (11)	0.29869 (5)	0.30339 (9)	0.01825 (14)
H16A	0.4631	0.2623	0.3713	0.031 (4)*
C17	0.43431 (11)	0.31333 (5)	0.19718 (10)	0.02080 (15)
H17A	0.5167	0.2874	0.1955	0.031 (4)*
C18	0.34281 (11)	0.36670 (5)	0.09358 (9)	0.02101 (15)
H18A	0.3639	0.3766	0.0227	0.028 (3)*
C19	0.21935 (11)	0.40523 (5)	0.09676 (9)	0.01935 (15)
H19A	0.1565	0.4404	0.0266	0.028 (3)*
C20	0.18935 (10)	0.39150 (5)	0.20449 (9)	0.01651 (13)
H20A	0.1078	0.4179	0.2067	0.024 (3)*
C21	0.36256 (10)	0.54910 (4)	0.53066 (9)	0.01771 (14)
H21A	0.4049	0.5586	0.4713	0.029 (3)*
H21B	0.4542	0.5496	0.6313	0.017 (3)*
H21C	0.2820	0.5857	0.5136	0.024 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0158 (2)	0.0189 (3)	0.0139 (2)	−0.00191 (19)	0.00978 (19)	−0.00217 (18)
O2	0.0206 (3)	0.0165 (3)	0.0189 (3)	−0.00460 (19)	0.0139 (2)	−0.00108 (19)
N1	0.0172 (3)	0.0168 (3)	0.0142 (3)	−0.0036 (2)	0.0103 (2)	−0.0021 (2)
N2	0.0171 (3)	0.0159 (3)	0.0155 (3)	−0.0024 (2)	0.0108 (2)	−0.0009 (2)
C1	0.0146 (3)	0.0154 (3)	0.0149 (3)	−0.0017 (2)	0.0088 (2)	−0.0004 (2)
C2	0.0204 (3)	0.0198 (4)	0.0174 (3)	−0.0043 (3)	0.0117 (3)	−0.0039 (3)
C3	0.0206 (3)	0.0182 (3)	0.0205 (3)	−0.0047 (3)	0.0112 (3)	−0.0034 (3)
C4	0.0195 (3)	0.0173 (3)	0.0222 (4)	−0.0033 (3)	0.0123 (3)	0.0009 (3)
C5	0.0188 (3)	0.0178 (3)	0.0188 (3)	−0.0020 (3)	0.0123 (3)	0.0012 (3)
C6	0.0147 (3)	0.0149 (3)	0.0151 (3)	−0.0004 (2)	0.0093 (2)	0.0003 (2)
C7	0.0146 (3)	0.0147 (3)	0.0137 (3)	−0.0007 (2)	0.0088 (2)	−0.0002 (2)
C8	0.0140 (3)	0.0147 (3)	0.0132 (3)	−0.0012 (2)	0.0081 (2)	−0.0004 (2)
C9	0.0183 (3)	0.0175 (3)	0.0148 (3)	−0.0020 (2)	0.0109 (3)	−0.0013 (2)
C10	0.0201 (3)	0.0182 (3)	0.0163 (3)	−0.0028 (3)	0.0115 (3)	−0.0032 (2)
C11	0.0181 (3)	0.0157 (3)	0.0166 (3)	−0.0028 (2)	0.0099 (3)	−0.0021 (2)
C12	0.0146 (3)	0.0154 (3)	0.0142 (3)	−0.0012 (2)	0.0086 (2)	0.0003 (2)
C13	0.0142 (3)	0.0146 (3)	0.0131 (3)	−0.0010 (2)	0.0082 (2)	−0.0008 (2)
C14	0.0199 (3)	0.0178 (3)	0.0178 (3)	0.0028 (3)	0.0127 (3)	0.0026 (3)
C15	0.0160 (3)	0.0142 (3)	0.0152 (3)	−0.0012 (2)	0.0098 (2)	−0.0012 (2)
C16	0.0202 (3)	0.0169 (3)	0.0204 (3)	0.0022 (3)	0.0131 (3)	0.0004 (3)
C17	0.0217 (3)	0.0228 (4)	0.0231 (4)	0.0008 (3)	0.0158 (3)	−0.0029 (3)
C18	0.0228 (4)	0.0272 (4)	0.0181 (3)	−0.0022 (3)	0.0145 (3)	−0.0022 (3)
C19	0.0210 (3)	0.0233 (4)	0.0159 (3)	0.0003 (3)	0.0116 (3)	0.0020 (3)
C20	0.0173 (3)	0.0186 (3)	0.0158 (3)	0.0008 (2)	0.0105 (3)	0.0013 (2)
C21	0.0177 (3)	0.0150 (3)	0.0207 (3)	−0.0020 (2)	0.0109 (3)	0.0025 (3)

Geometric parameters (Å, º)

O1—C13	1.3788 (9)	C9—H9A	0.9300
O1—C14	1.4439 (10)	C10—C11	1.3956 (11)
O2—C12	1.3623 (9)	C10—H10A	0.9300
O2—C21	1.4307 (10)	C11—C12	1.3903 (11)
N1—C7	1.3719 (10)	C11—H11A	0.9300
N1—C1	1.3755 (10)	C12—C13	1.4102 (11)
N1—H1A	0.8600	C14—C15	1.5026 (11)
N2—C7	1.3302 (10)	C14—H14A	0.9700
N2—C6	1.3857 (10)	C14—H14B	0.9700
C1—C2	1.3933 (11)	C15—C20	1.3909 (11)
C1—C6	1.4082 (11)	C15—C16	1.3991 (11)
C2—C3	1.3880 (12)	C16—C17	1.3913 (12)
C2—H2A	0.9299	C16—H16A	0.9300
C3—C4	1.4102 (12)	C17—C18	1.3903 (13)
C3—H3A	0.9299	C17—H17A	0.9299
C4—C5	1.3871 (12)	C18—C19	1.3931 (12)
C4—H4A	0.9300	C18—H18A	0.9299
C5—C6	1.4027 (11)	C19—C20	1.3954 (11)
C5—H5A	0.9300	C19—H19A	0.9300
C7—C8	1.4685 (11)	C20—H20A	0.9301
C8—C13	1.3979 (10)	C21—H21A	0.9600
C8—C9	1.4078 (11)	C21—H21B	0.9600
C9—C10	1.3833 (11)	C21—H21C	0.9599
C13—O1—C14	114.94 (6)	C10—C11—H11A	120.2
C12—O2—C21	116.76 (6)	O2—C12—C11	125.04 (7)
C7—N1—C1	107.18 (6)	O2—C12—C13	115.13 (7)
C7—N1—H1A	126.4	C11—C12—C13	119.83 (7)
C1—N1—H1A	126.4	O1—C13—C8	120.67 (7)
C7—N2—C6	104.67 (6)	O1—C13—C12	118.66 (7)
N1—C1—C2	131.70 (7)	C8—C13—C12	120.55 (7)
N1—C1—C6	105.19 (6)	O1—C14—C15	111.43 (6)
C2—C1—C6	123.10 (7)	O1—C14—H14A	109.3
C3—C2—C1	116.37 (8)	C15—C14—H14A	109.3
C3—C2—H2A	121.8	O1—C14—H14B	109.3
C1—C2—H2A	121.8	C15—C14—H14B	109.3
C2—C3—C4	121.60 (8)	H14A—C14—H14B	108.0
C2—C3—H3A	119.2	C20—C15—C16	119.41 (7)
C4—C3—H3A	119.2	C20—C15—C14	122.63 (7)
C5—C4—C3	121.47 (7)	C16—C15—C14	117.94 (7)
C5—C4—H4A	119.3	C17—C16—C15	120.39 (8)
C3—C4—H4A	119.3	C17—C16—H16A	119.8
C4—C5—C6	117.88 (8)	C15—C16—H16A	119.8
C4—C5—H5A	121.1	C18—C17—C16	120.17 (8)
C6—C5—H5A	121.1	C18—C17—H17A	119.9
N2—C6—C5	130.15 (7)	C16—C17—H17A	119.9
N2—C6—C1	110.28 (6)	C17—C18—C19	119.52 (8)
C5—C6—C1	119.57 (7)	C17—C18—H18A	120.2
N2—C7—N1	112.67 (7)	C19—C18—H18A	120.2
N2—C7—C8	123.71 (7)	C18—C19—C20	120.48 (8)
N1—C7—C8	123.51 (7)	C18—C19—H19A	119.8
C13—C8—C9	118.80 (7)	C20—C19—H19A	119.8
C13—C8—C7	122.79 (7)	C15—C20—C19	120.02 (7)
C9—C8—C7	118.35 (7)	C15—C20—H20A	120.0
C10—C9—C8	120.29 (7)	C19—C20—H20A	120.0
C10—C9—H9A	119.9	O2—C21—H21A	109.5
C8—C9—H9A	119.9	O2—C21—H21B	109.5
C9—C10—C11	121.01 (7)	H21A—C21—H21B	109.5
C9—C10—H10A	119.5	O2—C21—H21C	109.5
C11—C10—H10A	119.5	H21A—C21—H21C	109.5
C12—C11—C10	119.49 (7)	H21B—C21—H21C	109.5
C12—C11—H11A	120.3
C7—N1—C1—C2	178.22 (9)	C9—C10—C11—C12	0.61 (12)
C7—N1—C1—C6	−0.44 (8)	C21—O2—C12—C11	−3.25 (11)
N1—C1—C2—C3	−178.33 (8)	C21—O2—C12—C13	176.66 (7)
C6—C1—C2—C3	0.13 (12)	C10—C11—C12—O2	−179.29 (7)
C1—C2—C3—C4	−0.37 (13)	C10—C11—C12—C13	0.81 (12)
C2—C3—C4—C5	−0.12 (14)	C14—O1—C13—C8	−109.24 (8)
C3—C4—C5—C6	0.85 (13)	C14—O1—C13—C12	74.67 (9)
C7—N2—C6—C5	−179.01 (8)	C9—C8—C13—O1	−175.35 (7)
C7—N2—C6—C1	−0.01 (9)	C7—C8—C13—O1	1.62 (11)
C4—C5—C6—N2	177.85 (8)	C9—C8—C13—C12	0.67 (11)
C4—C5—C6—C1	−1.06 (12)	C7—C8—C13—C12	177.64 (7)
N1—C1—C6—N2	0.29 (9)	O2—C12—C13—O1	−5.26 (10)
C2—C1—C6—N2	−178.52 (8)	C11—C12—C13—O1	174.65 (7)
N1—C1—C6—C5	179.41 (7)	O2—C12—C13—C8	178.64 (7)
C2—C1—C6—C5	0.60 (12)	C11—C12—C13—C8	−1.45 (11)
C6—N2—C7—N1	−0.28 (9)	C13—O1—C14—C15	−135.66 (7)
C6—N2—C7—C8	176.04 (7)	O1—C14—C15—C20	13.36 (11)
C1—N1—C7—N2	0.47 (9)	O1—C14—C15—C16	−168.44 (7)
C1—N1—C7—C8	−175.86 (7)	C20—C15—C16—C17	1.50 (12)
N2—C7—C8—C13	175.53 (7)	C14—C15—C16—C17	−176.76 (8)
N1—C7—C8—C13	−8.53 (12)	C15—C16—C17—C18	−1.19 (13)
N2—C7—C8—C9	−7.48 (11)	C16—C17—C18—C19	−0.15 (13)
N1—C7—C8—C9	168.45 (7)	C17—C18—C19—C20	1.17 (13)
C13—C8—C9—C10	0.75 (12)	C16—C15—C20—C19	−0.47 (12)
C7—C8—C9—C10	−176.36 (7)	C14—C15—C20—C19	177.70 (8)
C8—C9—C10—C11	−1.40 (12)	C18—C19—C20—C15	−0.86 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	2.14	2.693 (1)	122
N1—H1A···N2^i	0.86	2.57	3.313 (1)	145

Symmetry code: (i) x, −y+1/2, z−1/2.