Ethyl 2-[4-(di-methyl-amino)-phen-yl]-1-phenyl-1H-benzimidazole-5-carboxyl-ate.

In the title compound, C24H23N3O2, the benzimidazole ring system makes dihedral angles of 7.28 (5) and 67.17 (5)°, respectively, with the planes of the benzene and phenyl rings, which in turn make a dihedral angle of 69.77 (6)°. In the crystal, mol-ecules are connected by C-H⋯N and C-H⋯O inter-actions, forming a layer parallel to the bc plane. A π-π inter-action, with a centroid-centroid distance of 3.656 (1) Å, is observed in the layer.

Related literature

For applications of benzimidazole compounds, see: Rao et al. (2002 ▶); Thakurdesai et al. (2007 ▶); McKellar & Scott (1990 ▶). For a related structure, see: Yoon et al. (2012 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C24H23N3O2

M = 385.45

Triclinic,

a = 8.7196 (1) Å

b = 10.4133 (2) Å

c = 11.3658 (2) Å

α = 79.312 (1)°

β = 74.393 (1)°

γ = 89.781 (1)°

V = 975.56 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.36 × 0.25 × 0.25 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.970, T max = 0.980

21016 measured reflections

5777 independent reflections

4602 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.125

S = 1.03

5777 reflections

265 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.30 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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813012440/is5269sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012440/is5269Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012440/is5269Isup3.cml

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

C24H23N3O2	Z = 2
Mr = 385.45	F(000) = 408
Triclinic, P1	Dx = 1.312 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7196 (1) Å	Cell parameters from 7512 reflections
b = 10.4133 (2) Å	θ = 2.5–30.2°
c = 11.3658 (2) Å	µ = 0.09 mm−1
α = 79.312 (1)°	T = 100 K
β = 74.393 (1)°	Block, yellow
γ = 89.781 (1)°	0.36 × 0.25 × 0.25 mm
V = 975.56 (3) Å3

Bruker SMART APEXII CCD area-detector diffractometer	5777 independent reflections
Radiation source: fine-focus sealed tube	4602 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 30.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
Tmin = 0.970, Tmax = 0.980	k = −14→14
21016 measured reflections	l = −15→16

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0552P)2 + 0.401P] where P = (Fo2 + 2Fc2)/3
5777 reflections	(Δ/σ)max = 0.001
265 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1	1.34962 (11)	−0.05308 (9)	0.29082 (8)	0.02242 (19)
O2	1.18718 (12)	0.04740 (9)	0.18312 (9)	0.0266 (2)
N1	0.98249 (12)	0.30045 (9)	0.65882 (9)	0.0171 (2)
N2	0.88283 (12)	0.33970 (10)	0.49238 (9)	0.0181 (2)
N3	0.41760 (14)	0.72466 (11)	0.79245 (11)	0.0251 (2)
C1	1.05977 (14)	0.22039 (11)	0.57924 (11)	0.0166 (2)
C2	1.17590 (15)	0.12968 (11)	0.58860 (11)	0.0191 (2)
H2A	1.2151	0.1116	0.6600	0.023*
C3	1.23128 (15)	0.06738 (11)	0.48914 (11)	0.0189 (2)
H3A	1.3098	0.0043	0.4923	0.023*
C4	1.17363 (14)	0.09557 (11)	0.38285 (11)	0.0171 (2)
C5	1.05674 (14)	0.18556 (11)	0.37516 (11)	0.0173 (2)
H5A	1.0180	0.2040	0.3036	0.021*
C6	0.99820 (14)	0.24776 (11)	0.47532 (11)	0.0167 (2)
C7	0.87548 (14)	0.37009 (11)	0.60175 (11)	0.0171 (2)
C8	0.76152 (14)	0.46126 (11)	0.65582 (11)	0.0178 (2)
C9	0.67109 (15)	0.52985 (12)	0.58132 (12)	0.0205 (2)
H9A	0.6880	0.5167	0.4984	0.025*
C10	0.55857 (15)	0.61573 (12)	0.62502 (12)	0.0216 (2)
H10A	0.5000	0.6602	0.5718	0.026*
C11	0.52922 (14)	0.63840 (11)	0.74735 (12)	0.0192 (2)
C12	0.61759 (14)	0.56812 (12)	0.82302 (12)	0.0197 (2)
H12A	0.5998	0.5801	0.9064	0.024*
C13	0.72998 (14)	0.48187 (12)	0.77812 (11)	0.0193 (2)
H13A	0.7870	0.4356	0.8317	0.023*
C14	1.02675 (14)	0.31301 (11)	0.76961 (11)	0.0169 (2)
C15	1.10245 (14)	0.42822 (12)	0.77495 (12)	0.0199 (2)
H15A	1.1247	0.4994	0.7062	0.024*
C16	1.14503 (15)	0.43744 (13)	0.88256 (12)	0.0234 (3)
H16A	1.1955	0.5160	0.8879	0.028*
C17	1.11435 (16)	0.33248 (14)	0.98248 (12)	0.0251 (3)
H17A	1.1432	0.3398	1.0559	0.030*
C18	1.04162 (15)	0.21708 (13)	0.97494 (12)	0.0234 (3)
H18A	1.0224	0.1450	1.0427	0.028*
C19	0.99673 (15)	0.20678 (12)	0.86827 (11)	0.0195 (2)
H19A	0.9462	0.1282	0.8630	0.023*
C20	1.23411 (14)	0.02962 (11)	0.27581 (11)	0.0186 (2)
C21	1.40780 (16)	−0.12580 (13)	0.19169 (12)	0.0237 (3)
H21A	1.4474	−0.0649	0.1109	0.028*
H21B	1.3210	−0.1834	0.1862	0.028*
C22	1.53955 (19)	−0.20550 (18)	0.22155 (17)	0.0406 (4)
H22A	1.5714	−0.2651	0.1628	0.061*
H22B	1.5030	−0.2564	0.3065	0.061*
H22C	1.6309	−0.1474	0.2150	0.061*
C23	0.34150 (17)	0.80634 (14)	0.70882 (14)	0.0289 (3)
H23A	0.2964	0.7515	0.6638	0.043*
H23B	0.4205	0.8701	0.6492	0.043*
H23C	0.2562	0.8526	0.7569	0.043*
C24	0.41620 (17)	0.76536 (13)	0.90791 (13)	0.0260 (3)
H24A	0.3841	0.6904	0.9770	0.039*
H24B	0.3404	0.8344	0.9219	0.039*
H24C	0.5231	0.7988	0.9029	0.039*

	U11	U22	U33	U12	U13	U23
O1	0.0267 (5)	0.0233 (4)	0.0198 (4)	0.0066 (4)	−0.0075 (4)	−0.0088 (3)
O2	0.0379 (5)	0.0266 (5)	0.0194 (5)	0.0062 (4)	−0.0131 (4)	−0.0072 (4)
N1	0.0224 (5)	0.0161 (5)	0.0155 (5)	0.0039 (4)	−0.0093 (4)	−0.0038 (4)
N2	0.0211 (5)	0.0175 (5)	0.0164 (5)	0.0018 (4)	−0.0070 (4)	−0.0023 (4)
N3	0.0284 (6)	0.0242 (5)	0.0256 (6)	0.0092 (4)	−0.0107 (5)	−0.0074 (4)
C1	0.0210 (5)	0.0147 (5)	0.0148 (5)	0.0002 (4)	−0.0062 (4)	−0.0031 (4)
C2	0.0247 (6)	0.0177 (5)	0.0174 (5)	0.0034 (4)	−0.0105 (5)	−0.0028 (4)
C3	0.0237 (6)	0.0164 (5)	0.0183 (6)	0.0035 (4)	−0.0085 (5)	−0.0033 (4)
C4	0.0214 (5)	0.0144 (5)	0.0156 (5)	−0.0008 (4)	−0.0056 (4)	−0.0022 (4)
C5	0.0216 (5)	0.0173 (5)	0.0143 (5)	−0.0005 (4)	−0.0076 (4)	−0.0019 (4)
C6	0.0194 (5)	0.0146 (5)	0.0166 (5)	−0.0001 (4)	−0.0073 (4)	−0.0011 (4)
C7	0.0200 (5)	0.0145 (5)	0.0169 (5)	0.0005 (4)	−0.0072 (4)	−0.0001 (4)
C8	0.0197 (5)	0.0159 (5)	0.0179 (5)	0.0007 (4)	−0.0067 (4)	−0.0012 (4)
C9	0.0240 (6)	0.0217 (6)	0.0173 (6)	0.0036 (5)	−0.0087 (5)	−0.0034 (4)
C10	0.0232 (6)	0.0214 (6)	0.0219 (6)	0.0045 (5)	−0.0102 (5)	−0.0020 (5)
C11	0.0190 (5)	0.0167 (5)	0.0218 (6)	0.0010 (4)	−0.0060 (5)	−0.0026 (4)
C12	0.0215 (6)	0.0199 (6)	0.0180 (6)	0.0018 (4)	−0.0064 (4)	−0.0028 (4)
C13	0.0217 (6)	0.0190 (5)	0.0174 (5)	0.0021 (4)	−0.0072 (4)	−0.0013 (4)
C14	0.0195 (5)	0.0194 (5)	0.0141 (5)	0.0046 (4)	−0.0074 (4)	−0.0049 (4)
C15	0.0213 (6)	0.0193 (6)	0.0195 (6)	0.0023 (4)	−0.0053 (4)	−0.0050 (4)
C16	0.0223 (6)	0.0270 (6)	0.0240 (6)	0.0006 (5)	−0.0076 (5)	−0.0108 (5)
C17	0.0244 (6)	0.0356 (7)	0.0193 (6)	0.0040 (5)	−0.0101 (5)	−0.0095 (5)
C18	0.0254 (6)	0.0286 (6)	0.0166 (6)	0.0041 (5)	−0.0086 (5)	−0.0010 (5)
C19	0.0220 (6)	0.0187 (5)	0.0191 (6)	0.0020 (4)	−0.0084 (5)	−0.0026 (4)
C20	0.0224 (6)	0.0154 (5)	0.0178 (6)	−0.0008 (4)	−0.0053 (4)	−0.0029 (4)
C21	0.0261 (6)	0.0239 (6)	0.0218 (6)	0.0023 (5)	−0.0035 (5)	−0.0107 (5)
C22	0.0298 (7)	0.0525 (10)	0.0517 (10)	0.0160 (7)	−0.0183 (7)	−0.0301 (8)
C23	0.0271 (7)	0.0285 (7)	0.0343 (7)	0.0102 (5)	−0.0137 (6)	−0.0062 (6)
C24	0.0272 (6)	0.0243 (6)	0.0260 (7)	0.0052 (5)	−0.0054 (5)	−0.0065 (5)

O1—C20	1.3478 (14)	C11—C12	1.4099 (16)
O1—C21	1.4513 (15)	C12—C13	1.3862 (17)
O2—C20	1.2127 (15)	C12—H12A	0.9500
N1—C1	1.3837 (15)	C13—H13A	0.9500
N1—C7	1.4011 (14)	C14—C15	1.3904 (17)
N1—C14	1.4404 (14)	C14—C19	1.3907 (16)
N2—C7	1.3238 (15)	C15—C16	1.3897 (17)
N2—C6	1.3866 (15)	C15—H15A	0.9500
N3—C11	1.3829 (16)	C16—C17	1.3908 (19)
N3—C24	1.4489 (17)	C16—H16A	0.9500
N3—C23	1.4500 (17)	C17—C18	1.3882 (19)
C1—C2	1.3937 (16)	C17—H17A	0.9500
C1—C6	1.4070 (16)	C18—C19	1.3923 (17)
C2—C3	1.3813 (17)	C18—H18A	0.9500
C2—H2A	0.9500	C19—H19A	0.9500
C3—C4	1.4115 (16)	C21—C22	1.491 (2)
C3—H3A	0.9500	C21—H21A	0.9900
C4—C5	1.3909 (16)	C21—H21B	0.9900
C4—C20	1.4805 (17)	C22—H22A	0.9800
C5—C6	1.3908 (17)	C22—H22B	0.9800
C5—H5A	0.9500	C22—H22C	0.9800
C7—C8	1.4653 (16)	C23—H23A	0.9800
C8—C13	1.3995 (17)	C23—H23B	0.9800
C8—C9	1.4069 (16)	C23—H23C	0.9800
C9—C10	1.3802 (17)	C24—H24A	0.9800
C9—H9A	0.9500	C24—H24B	0.9800
C10—C11	1.4087 (18)	C24—H24C	0.9800
C10—H10A	0.9500
C20—O1—C21	115.44 (10)	C8—C13—H13A	119.2
C1—N1—C7	106.59 (9)	C15—C14—C19	121.28 (11)
C1—N1—C14	122.51 (9)	C15—C14—N1	120.01 (10)
C7—N1—C14	130.52 (10)	C19—C14—N1	118.68 (11)
C7—N2—C6	105.79 (10)	C16—C15—C14	118.87 (11)
C11—N3—C24	119.19 (11)	C16—C15—H15A	120.6
C11—N3—C23	119.82 (11)	C14—C15—H15A	120.6
C24—N3—C23	117.76 (11)	C15—C16—C17	120.50 (12)
N1—C1—C2	131.70 (11)	C15—C16—H16A	119.8
N1—C1—C6	105.58 (10)	C17—C16—H16A	119.8
C2—C1—C6	122.72 (11)	C18—C17—C16	120.03 (12)
C3—C2—C1	116.81 (11)	C18—C17—H17A	120.0
C3—C2—H2A	121.6	C16—C17—H17A	120.0
C1—C2—H2A	121.6	C17—C18—C19	120.16 (12)
C2—C3—C4	121.33 (11)	C17—C18—H18A	119.9
C2—C3—H3A	119.3	C19—C18—H18A	119.9
C4—C3—H3A	119.3	C14—C19—C18	119.14 (12)
C5—C4—C3	121.25 (11)	C14—C19—H19A	120.4
C5—C4—C20	117.45 (10)	C18—C19—H19A	120.4
C3—C4—C20	121.30 (11)	O2—C20—O1	122.55 (11)
C6—C5—C4	118.08 (10)	O2—C20—C4	124.51 (11)
C6—C5—H5A	121.0	O1—C20—C4	112.95 (10)
C4—C5—H5A	121.0	O1—C21—C22	107.42 (11)
N2—C6—C5	130.04 (11)	O1—C21—H21A	110.2
N2—C6—C1	110.18 (10)	C22—C21—H21A	110.2
C5—C6—C1	119.77 (11)	O1—C21—H21B	110.2
N2—C7—N1	111.84 (10)	C22—C21—H21B	110.2
N2—C7—C8	122.37 (10)	H21A—C21—H21B	108.5
N1—C7—C8	125.72 (11)	C21—C22—H22A	109.5
C13—C8—C9	116.88 (11)	C21—C22—H22B	109.5
C13—C8—C7	125.18 (11)	H22A—C22—H22B	109.5
C9—C8—C7	117.88 (11)	C21—C22—H22C	109.5
C10—C9—C8	122.03 (12)	H22A—C22—H22C	109.5
C10—C9—H9A	119.0	H22B—C22—H22C	109.5
C8—C9—H9A	119.0	N3—C23—H23A	109.5
C9—C10—C11	121.03 (11)	N3—C23—H23B	109.5
C9—C10—H10A	119.5	H23A—C23—H23B	109.5
C11—C10—H10A	119.5	N3—C23—H23C	109.5
N3—C11—C10	121.81 (11)	H23A—C23—H23C	109.5
N3—C11—C12	121.07 (11)	H23B—C23—H23C	109.5
C10—C11—C12	117.11 (11)	N3—C24—H24A	109.5
C13—C12—C11	121.30 (11)	N3—C24—H24B	109.5
C13—C12—H12A	119.4	H24A—C24—H24B	109.5
C11—C12—H12A	119.4	N3—C24—H24C	109.5
C12—C13—C8	121.63 (11)	H24A—C24—H24C	109.5
C12—C13—H13A	119.2	H24B—C24—H24C	109.5
C7—N1—C1—C2	−179.19 (12)	C8—C9—C10—C11	−0.05 (19)
C14—N1—C1—C2	7.2 (2)	C24—N3—C11—C10	−166.84 (12)
C7—N1—C1—C6	1.38 (12)	C23—N3—C11—C10	−7.59 (19)
C14—N1—C1—C6	−172.24 (10)	C24—N3—C11—C12	13.84 (18)
N1—C1—C2—C3	−178.49 (12)	C23—N3—C11—C12	173.09 (12)
C6—C1—C2—C3	0.86 (18)	C9—C10—C11—N3	179.62 (12)
C1—C2—C3—C4	0.58 (18)	C9—C10—C11—C12	−1.04 (18)
C2—C3—C4—C5	−1.15 (18)	N3—C11—C12—C13	−179.78 (12)
C2—C3—C4—C20	179.44 (11)	C10—C11—C12—C13	0.87 (18)
C3—C4—C5—C6	0.24 (17)	C11—C12—C13—C8	0.40 (19)
C20—C4—C5—C6	179.67 (10)	C9—C8—C13—C12	−1.47 (18)
C7—N2—C6—C5	−178.08 (12)	C7—C8—C13—C12	−178.60 (11)
C7—N2—C6—C1	1.17 (13)	C1—N1—C14—C15	108.78 (13)
C4—C5—C6—N2	−179.65 (11)	C7—N1—C14—C15	−63.17 (17)
C4—C5—C6—C1	1.16 (17)	C1—N1—C14—C19	−69.23 (15)
N1—C1—C6—N2	−1.61 (13)	C7—N1—C14—C19	118.82 (13)
C2—C1—C6—N2	178.89 (11)	C19—C14—C15—C16	−1.54 (18)
N1—C1—C6—C5	177.73 (10)	N1—C14—C15—C16	−179.49 (11)
C2—C1—C6—C5	−1.76 (18)	C14—C15—C16—C17	0.87 (19)
C6—N2—C7—N1	−0.27 (13)	C15—C16—C17—C18	0.43 (19)
C6—N2—C7—C8	−177.42 (10)	C16—C17—C18—C19	−1.10 (19)
C1—N1—C7—N2	−0.73 (13)	C15—C14—C19—C18	0.88 (18)
C14—N1—C7—N2	172.19 (11)	N1—C14—C19—C18	178.86 (11)
C1—N1—C7—C8	176.31 (11)	C17—C18—C19—C14	0.45 (19)
C14—N1—C7—C8	−10.77 (19)	C21—O1—C20—O2	−3.58 (17)
N2—C7—C8—C13	169.33 (11)	C21—O1—C20—C4	176.91 (10)
N1—C7—C8—C13	−7.41 (19)	C5—C4—C20—O2	−1.07 (18)
N2—C7—C8—C9	−7.78 (17)	C3—C4—C20—O2	178.36 (12)
N1—C7—C8—C9	175.48 (11)	C5—C4—C20—O1	178.43 (10)
C13—C8—C9—C10	1.30 (18)	C3—C4—C20—O1	−2.14 (16)
C7—C8—C9—C10	178.65 (11)	C20—O1—C21—C22	177.00 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···N2i	0.95	2.57	3.4868 (16)	164
C18—H18A···O2ii	0.95	2.50	3.2217 (17)	133
C19—H19A···O2iii	0.95	2.38	3.3209 (16)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯N2i	0.95	2.57	3.4868 (16)	164
C18—H18A⋯O2ii	0.95	2.50	3.2217 (17)	133
C19—H19A⋯O2iii	0.95	2.38	3.3209 (16)	170

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