4-(1-Ethyl-1H-1,3-benzimidazol-2-yl)-N,N-diphenyl-aniline monohydrate.

In the title compound, C(27)H(23)N(3)O·H(2)O, the benzimidazole ring system has an r.m.s. deviation of 0.0071 Å and makes dihedral angles of 34.51 (2), 55.22 (3) and 41.05 (5)° with the central and N-bonded phenyl rings, respectively. In the crystal, the water mol-ecular is connected to the organic mol-ecule by inter-molecular O-H⋯N hydrogen bonds. Weak inter-molecular C-H⋯O hydrogen bonds also occur.

Related literature

For the synthetic procedure, see: Vinodkumar et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶). For background to the use of the title compound as an inter­mediate in the preparation of OLED materials, see: Kakimoto et al. (2008 ▶).

Experimental

Crystal data

C27H23N3·H2O

M = 407.50

Monoclinic,

a = 12.278 (3) Å

b = 9.2690 (19) Å

c = 19.468 (4) Å

β = 97.81 (3)°

V = 2195.0 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.978, T max = 0.992

4223 measured reflections

4024 independent reflections

2487 reflections with I > 2σ(I)

R int = 0.025

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.169

S = 1.01

4024 reflections

281 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100119X/bq2268sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100119X/bq2268Isup2.hkl

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

C27H23N3·H2O	F(000) = 864
Mr = 407.50	Dx = 1.233 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 12.278 (3) Å	θ = 10–14°
b = 9.2690 (19) Å	µ = 0.08 mm−1
c = 19.468 (4) Å	T = 293 K
β = 97.81 (3)°	Block, colorless
V = 2195.0 (8) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2487 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
graphite	θmax = 25.4°, θmin = 1.7°
ω/2θ scans	h = 0→14
Absorption correction: ψ scan (North et al., 1968)	k = 0→11
Tmin = 0.978, Tmax = 0.992	l = −23→23
4223 measured reflections	3 standard reflections every 200 reflections
4024 independent reflections	intensity decay: 1%

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)] = 0.057	H-atom parameters constrained
wR(F2) = 0.169	w = 1/[σ2(Fo2) + (0.090P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
4024 reflections	Δρmax = 0.18 e Å−3
281 parameters	Δρmin = −0.26 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0093 (17)

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
N1	0.12417 (17)	0.8084 (2)	−0.08205 (12)	0.0535 (6)
C1	0.0167 (2)	1.0299 (3)	−0.09280 (14)	0.0502 (7)
H1A	−0.0468	0.9764	−0.0906	0.060*
N2	0.53509 (16)	0.6320 (2)	0.14215 (10)	0.0457 (5)
C2	0.0102 (2)	1.1782 (3)	−0.10031 (16)	0.0599 (8)
H2B	−0.0578	1.2238	−0.1038	0.072*
N3	0.47737 (16)	0.4037 (2)	0.12179 (11)	0.0435 (5)
C3	0.1033 (3)	1.2582 (3)	−0.10260 (16)	0.0622 (8)
H3A	0.0986	1.3580	−0.1072	0.075*
C4	0.2031 (2)	1.1914 (3)	−0.09818 (15)	0.0567 (7)
H4A	0.2664	1.2461	−0.0993	0.068*
C5	0.2108 (2)	1.0429 (3)	−0.09211 (14)	0.0522 (7)
H5A	0.2787	0.9977	−0.0905	0.063*
C6	0.1169 (2)	0.9614 (3)	−0.08850 (13)	0.0442 (6)
C7	0.03574 (19)	0.7225 (3)	−0.11420 (13)	0.0419 (6)
C8	−0.0220 (2)	0.6349 (3)	−0.07465 (15)	0.0514 (7)
H8A	−0.0017	0.6299	−0.0269	0.062*
C9	−0.1095 (2)	0.5549 (3)	−0.10554 (18)	0.0625 (8)
H9A	−0.1477	0.4955	−0.0786	0.075*
C10	−0.1405 (3)	0.5620 (3)	−0.1750 (2)	0.0737 (10)
H10A	−0.2004	0.5088	−0.1956	0.088*
C11	−0.0834 (3)	0.6476 (4)	−0.21467 (17)	0.0733 (9)
H11A	−0.1042	0.6516	−0.2624	0.088*
C12	0.0048 (2)	0.7282 (3)	−0.18469 (14)	0.0609 (8)
H12A	0.0433	0.7861	−0.2121	0.073*
C13	0.20766 (19)	0.7440 (3)	−0.03508 (13)	0.0431 (6)
C14	0.2497 (2)	0.8104 (3)	0.02666 (13)	0.0461 (6)
H14A	0.2234	0.9005	0.0375	0.055*
C15	0.3298 (2)	0.7442 (3)	0.07189 (13)	0.0443 (6)
H15A	0.3578	0.7910	0.1128	0.053*
C16	0.37033 (19)	0.6077 (3)	0.05776 (13)	0.0408 (6)
C17	0.32912 (19)	0.5432 (3)	−0.00436 (13)	0.0435 (6)
H17A	0.3560	0.4536	−0.0154	0.052*
C18	0.2488 (2)	0.6091 (3)	−0.05033 (13)	0.0446 (6)
H18A	0.2220	0.5633	−0.0917	0.053*
C19	0.4598 (2)	0.5481 (3)	0.10699 (13)	0.0419 (6)
C20	0.6054 (2)	0.5389 (3)	0.18193 (13)	0.0457 (6)
C21	0.6991 (2)	0.5681 (3)	0.22815 (14)	0.0560 (7)
H21A	0.7225	0.6625	0.2371	0.067*
C22	0.7562 (3)	0.4543 (4)	0.26021 (16)	0.0706 (9)
H22A	0.8196	0.4716	0.2910	0.085*
C23	0.7204 (3)	0.3122 (3)	0.24720 (16)	0.0681 (9)
H23A	0.7611	0.2374	0.2697	0.082*
C24	0.6278 (2)	0.2793 (3)	0.20264 (15)	0.0587 (8)
H24A	0.6040	0.1847	0.1947	0.070*
C25	0.5710 (2)	0.3962 (3)	0.16973 (13)	0.0443 (6)
C26	0.4069 (2)	0.2785 (3)	0.10055 (15)	0.0556 (7)
H26A	0.3350	0.3125	0.0803	0.067*
H26B	0.3975	0.2221	0.1413	0.067*
C27	0.4534 (3)	0.1826 (3)	0.04887 (17)	0.0717 (9)
H27A	0.4046	0.1029	0.0370	0.108*
H27B	0.5241	0.1471	0.0689	0.108*
H27C	0.4611	0.2371	0.0079	0.108*
OW	0.5578 (2)	0.9300 (3)	0.18768 (15)	0.1158 (10)
HWB	0.5151	0.8673	0.2015	0.139*
HWA	0.5919	0.8888	0.1579	0.139*

	U11	U22	U33	U12	U13	U23
N1	0.0452 (12)	0.0373 (12)	0.0720 (15)	−0.0054 (10)	−0.0136 (11)	0.0103 (11)
C1	0.0447 (15)	0.0436 (16)	0.0618 (18)	−0.0048 (12)	0.0060 (13)	−0.0013 (13)
N2	0.0466 (12)	0.0395 (12)	0.0487 (13)	0.0007 (10)	−0.0017 (10)	0.0037 (10)
C2	0.0593 (18)	0.0438 (17)	0.076 (2)	0.0047 (14)	0.0084 (15)	−0.0064 (14)
N3	0.0456 (12)	0.0314 (11)	0.0524 (13)	−0.0009 (9)	0.0030 (10)	0.0064 (9)
C3	0.076 (2)	0.0335 (15)	0.076 (2)	−0.0049 (15)	0.0059 (17)	−0.0042 (14)
C4	0.0601 (18)	0.0439 (17)	0.0637 (18)	−0.0169 (14)	−0.0005 (14)	0.0051 (14)
C5	0.0432 (14)	0.0482 (16)	0.0631 (18)	−0.0050 (13)	−0.0007 (13)	0.0064 (14)
C6	0.0455 (14)	0.0373 (14)	0.0476 (15)	−0.0025 (12)	−0.0012 (12)	0.0054 (12)
C7	0.0381 (13)	0.0333 (13)	0.0520 (16)	−0.0002 (11)	−0.0019 (12)	0.0013 (11)
C8	0.0511 (15)	0.0469 (16)	0.0554 (17)	−0.0007 (13)	0.0041 (13)	0.0050 (13)
C9	0.0478 (16)	0.0487 (17)	0.090 (2)	−0.0096 (14)	0.0067 (16)	0.0052 (16)
C10	0.0583 (19)	0.0508 (19)	0.104 (3)	−0.0061 (16)	−0.0186 (19)	−0.0158 (19)
C11	0.085 (2)	0.071 (2)	0.0557 (19)	0.004 (2)	−0.0171 (18)	−0.0122 (17)
C12	0.0669 (19)	0.0648 (19)	0.0495 (17)	−0.0021 (16)	0.0026 (15)	0.0044 (14)
C13	0.0378 (13)	0.0357 (14)	0.0544 (16)	−0.0037 (11)	0.0013 (12)	0.0076 (12)
C14	0.0448 (14)	0.0386 (14)	0.0537 (16)	0.0036 (12)	0.0025 (12)	−0.0012 (12)
C15	0.0458 (14)	0.0399 (14)	0.0458 (15)	−0.0016 (12)	0.0009 (12)	−0.0031 (11)
C16	0.0377 (13)	0.0367 (14)	0.0476 (15)	−0.0032 (11)	0.0040 (11)	0.0025 (11)
C17	0.0415 (13)	0.0332 (13)	0.0560 (16)	−0.0002 (11)	0.0073 (12)	−0.0011 (12)
C18	0.0450 (14)	0.0381 (14)	0.0487 (15)	−0.0049 (12)	−0.0003 (12)	−0.0016 (12)
C19	0.0430 (13)	0.0360 (14)	0.0469 (14)	−0.0002 (12)	0.0063 (11)	0.0028 (12)
C20	0.0463 (15)	0.0440 (15)	0.0460 (15)	0.0011 (12)	0.0041 (12)	0.0036 (12)
C21	0.0570 (17)	0.0506 (17)	0.0563 (17)	−0.0022 (14)	−0.0067 (14)	0.0013 (14)
C22	0.0651 (19)	0.076 (2)	0.064 (2)	0.0051 (18)	−0.0142 (16)	0.0095 (17)
C23	0.072 (2)	0.061 (2)	0.067 (2)	0.0176 (17)	−0.0079 (17)	0.0206 (16)
C24	0.0676 (19)	0.0433 (16)	0.0645 (19)	0.0062 (14)	0.0067 (16)	0.0122 (14)
C25	0.0469 (14)	0.0404 (14)	0.0458 (15)	0.0033 (12)	0.0072 (12)	0.0076 (12)
C26	0.0544 (16)	0.0392 (15)	0.0715 (19)	−0.0095 (13)	0.0032 (14)	0.0105 (14)
C27	0.077 (2)	0.0437 (17)	0.091 (2)	−0.0017 (16)	−0.0020 (18)	−0.0060 (16)
OW	0.154 (2)	0.0616 (15)	0.146 (2)	−0.0265 (16)	0.073 (2)	−0.0184 (15)

N1—C13	1.410 (3)	C13—C14	1.386 (4)
N1—C7	1.421 (3)	C13—C18	1.396 (3)
N1—C6	1.426 (3)	C14—C15	1.373 (3)
C1—C6	1.377 (3)	C14—H14A	0.9300
C1—C2	1.383 (4)	C15—C16	1.401 (3)
C1—H1A	0.9300	C15—H15A	0.9300
N2—C19	1.324 (3)	C16—C17	1.382 (3)
N2—C20	1.381 (3)	C16—C19	1.464 (3)
C2—C3	1.369 (4)	C17—C18	1.380 (3)
C2—H2B	0.9300	C17—H17A	0.9300
N3—C19	1.380 (3)	C18—H18A	0.9300
N3—C25	1.381 (3)	C20—C21	1.388 (3)
N3—C26	1.473 (3)	C20—C25	1.398 (4)
C3—C4	1.365 (4)	C21—C22	1.369 (4)
C3—H3A	0.9300	C21—H21A	0.9300
C4—C5	1.384 (4)	C22—C23	1.401 (4)
C4—H4A	0.9300	C22—H22A	0.9300
C5—C6	1.388 (3)	C23—C24	1.368 (4)
C5—H5A	0.9300	C23—H23A	0.9300
C7—C12	1.374 (4)	C24—C25	1.397 (3)
C7—C8	1.380 (3)	C24—H24A	0.9300
C8—C9	1.375 (4)	C26—C27	1.511 (4)
C8—H8A	0.9300	C26—H26A	0.9700
C9—C10	1.356 (5)	C26—H26B	0.9700
C9—H9A	0.9300	C27—H27A	0.9600
C10—C11	1.365 (5)	C27—H27B	0.9600
C10—H10A	0.9300	C27—H27C	0.9600
C11—C12	1.378 (4)	OW—HWB	0.8499
C11—H11A	0.9300	OW—HWA	0.8501
C12—H12A	0.9300
C13—N1—C7	119.5 (2)	C13—C14—H14A	119.7
C13—N1—C6	120.7 (2)	C14—C15—C16	121.4 (2)
C7—N1—C6	118.9 (2)	C14—C15—H15A	119.3
C6—C1—C2	120.2 (3)	C16—C15—H15A	119.3
C6—C1—H1A	119.9	C17—C16—C15	117.7 (2)
C2—C1—H1A	119.9	C17—C16—C19	124.3 (2)
C19—N2—C20	105.2 (2)	C15—C16—C19	117.8 (2)
C3—C2—C1	120.4 (3)	C18—C17—C16	121.4 (2)
C3—C2—H2B	119.8	C18—C17—H17A	119.3
C1—C2—H2B	119.8	C16—C17—H17A	119.3
C19—N3—C25	106.37 (19)	C17—C18—C13	120.4 (2)
C19—N3—C26	129.6 (2)	C17—C18—H18A	119.8
C25—N3—C26	123.6 (2)	C13—C18—H18A	119.8
C4—C3—C2	119.9 (3)	N2—C19—N3	112.5 (2)
C4—C3—H3A	120.0	N2—C19—C16	121.7 (2)
C2—C3—H3A	120.0	N3—C19—C16	125.7 (2)
C3—C4—C5	120.4 (3)	N2—C20—C21	129.9 (2)
C3—C4—H4A	119.8	N2—C20—C25	110.1 (2)
C5—C4—H4A	119.8	C21—C20—C25	120.0 (2)
C4—C5—C6	119.9 (3)	C22—C21—C20	118.2 (3)
C4—C5—H5A	120.1	C22—C21—H21A	120.9
C6—C5—H5A	120.1	C20—C21—H21A	120.9
C1—C6—C5	119.2 (2)	C21—C22—C23	120.9 (3)
C1—C6—N1	120.6 (2)	C21—C22—H22A	119.6
C5—C6—N1	120.2 (2)	C23—C22—H22A	119.6
C12—C7—C8	119.1 (2)	C24—C23—C22	122.6 (3)
C12—C7—N1	120.6 (2)	C24—C23—H23A	118.7
C8—C7—N1	120.3 (2)	C22—C23—H23A	118.7
C9—C8—C7	120.3 (3)	C23—C24—C25	116.0 (3)
C9—C8—H8A	119.9	C23—C24—H24A	122.0
C7—C8—H8A	119.9	C25—C24—H24A	122.0
C10—C9—C8	120.4 (3)	N3—C25—C24	131.8 (2)
C10—C9—H9A	119.8	N3—C25—C20	105.8 (2)
C8—C9—H9A	119.8	C24—C25—C20	122.4 (2)
C9—C10—C11	119.8 (3)	N3—C26—C27	112.9 (2)
C9—C10—H10A	120.1	N3—C26—H26A	109.0
C11—C10—H10A	120.1	C27—C26—H26A	109.0
C10—C11—C12	120.6 (3)	N3—C26—H26B	109.0
C10—C11—H11A	119.7	C27—C26—H26B	109.0
C12—C11—H11A	119.7	H26A—C26—H26B	107.8
C7—C12—C11	119.8 (3)	C26—C27—H27A	109.5
C7—C12—H12A	120.1	C26—C27—H27B	109.5
C11—C12—H12A	120.1	H27A—C27—H27B	109.5
C14—C13—C18	118.6 (2)	C26—C27—H27C	109.5
C14—C13—N1	121.8 (2)	H27A—C27—H27C	109.5
C18—C13—N1	119.6 (2)	H27B—C27—H27C	109.5
C15—C14—C13	120.5 (2)	HWB—OW—HWA	106.9
C15—C14—H14A	119.7
C6—C1—C2—C3	−0.9 (4)	C19—C16—C17—C18	−176.2 (2)
C1—C2—C3—C4	0.7 (5)	C16—C17—C18—C13	0.4 (4)
C2—C3—C4—C5	0.7 (4)	C14—C13—C18—C17	0.5 (4)
C3—C4—C5—C6	−1.8 (4)	N1—C13—C18—C17	−178.8 (2)
C2—C1—C6—C5	−0.3 (4)	C20—N2—C19—N3	0.0 (3)
C2—C1—C6—N1	−178.8 (3)	C20—N2—C19—C16	−179.3 (2)
C4—C5—C6—C1	1.6 (4)	C25—N3—C19—N2	−0.2 (3)
C4—C5—C6—N1	−179.8 (3)	C26—N3—C19—N2	172.0 (2)
C13—N1—C6—C1	−136.8 (3)	C25—N3—C19—C16	179.0 (2)
C7—N1—C6—C1	32.2 (4)	C26—N3—C19—C16	−8.7 (4)
C13—N1—C6—C5	44.7 (4)	C17—C16—C19—N2	142.4 (3)
C7—N1—C6—C5	−146.3 (2)	C15—C16—C19—N2	−32.3 (3)
C13—N1—C7—C12	−130.9 (3)	C17—C16—C19—N3	−36.8 (4)
C6—N1—C7—C12	59.9 (3)	C15—C16—C19—N3	148.5 (2)
C13—N1—C7—C8	50.7 (3)	C19—N2—C20—C21	179.5 (3)
C6—N1—C7—C8	−118.5 (3)	C19—N2—C20—C25	0.2 (3)
C12—C7—C8—C9	−0.2 (4)	N2—C20—C21—C22	−178.5 (3)
N1—C7—C8—C9	178.2 (2)	C25—C20—C21—C22	0.6 (4)
C7—C8—C9—C10	−0.5 (4)	C20—C21—C22—C23	−0.6 (5)
C8—C9—C10—C11	1.0 (5)	C21—C22—C23—C24	−0.2 (5)
C9—C10—C11—C12	−0.7 (5)	C22—C23—C24—C25	0.8 (5)
C8—C7—C12—C11	0.5 (4)	C19—N3—C25—C24	−179.4 (3)
N1—C7—C12—C11	−177.9 (3)	C26—N3—C25—C24	7.8 (4)
C10—C11—C12—C7	−0.1 (5)	C19—N3—C25—C20	0.4 (3)
C7—N1—C13—C14	−137.3 (3)	C26—N3—C25—C20	−172.5 (2)
C6—N1—C13—C14	31.7 (4)	C23—C24—C25—N3	178.9 (3)
C7—N1—C13—C18	42.1 (3)	C23—C24—C25—C20	−0.8 (4)
C6—N1—C13—C18	−149.0 (2)	N2—C20—C25—N3	−0.4 (3)
C18—C13—C14—C15	−0.3 (4)	C21—C20—C25—N3	−179.7 (2)
N1—C13—C14—C15	179.0 (2)	N2—C20—C25—C24	179.4 (2)
C13—C14—C15—C16	−0.9 (4)	C21—C20—C25—C24	0.0 (4)
C14—C15—C16—C17	1.8 (4)	C19—N3—C26—C27	110.2 (3)
C14—C15—C16—C19	176.8 (2)	C25—N3—C26—C27	−78.7 (3)
C15—C16—C17—C18	−1.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
OW—HWB···N2	0.85	2.50	2.903 (3)	110
OW—HWA···N2	0.85	2.49	2.903 (3)	111
C24—H24A···OWi	0.93	2.43	3.352 (4)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
OW—HWB⋯N2	0.85	2.50	2.903 (3)	110
OW—HWA⋯N2	0.85	2.49	2.903 (3)	111
C24—H24A⋯OWi	0.93	2.43	3.352 (4)	173

Symmetry code: (i) .