4-(1-Ethyl-1H-1,3-benzimidazol-2-yl)-N,N-diphenyl­aniline monohydrate

Wu, T.; Wang, K.; Jiang, P.; Zhu, H.-J.

doi:10.1107/S160053681100119X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o417

doi:10.1107/S160053681100119X

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4-(1-Ethyl-1H-1,3-benzimidazol-2-yl)-N,N-diphenylaniline monohydrate

Tao Wu,^a Kai Wang,^a Peng Jiang ^a and Hong-Jun Zhu ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: zhuhj@njut.edu.cn

(Received 23 December 2010; accepted 9 January 2011; online 15 January 2011)

In the title compound, C₂₇H₂₃N₃O·H₂O, 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 molecular is connected to the organic molecule by intermolecular O—H⋯N hydrogen bonds. Weak intermolecular 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_r = 407.50
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.057
wR(F²) = 0.169
S = 1.01
4024 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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) x, y-1, z.

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.

Supporting information

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

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

checkCIF report

Comment top

The title compound, (I), is a kind of important organic intermediate which can be used for many fields such as OLED materials. (Kakimoto et al., 2008). We herein report its crystal structure.

In the molecule of (I), (Fig.1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. The benzimidazole ring (A) is obviously almost coplanar with an r.m.s. deviation of 0.0071 °. The dihedral angles between A and the rest three phenyl rings B (C13-C18), C (C7-C12) and D (C1-C6) are 34.51 (2) ° 55.22 (3) ° and 41.05 (5) °, respectively. The H₂O molecule stems from the solvent ethanol, and the water molecular is connected with the target molecular by intermolecular C—H···O and O—H···N hydrogen bonds (Table 1), which seems to be very effective in the stabilization of the crystal structure.

Related literature top

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). Scheme - show water as H₂O

Experimental top

The title compound, (I) was synthesized according to the literature (Vinodkumar et al., 2008) The crystals were obtained by dissolving (I) (0.52 g, 1.28 mmol) in 25 ml ethanol and evaporating the solvent slowly at room temperature for about 7 d.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

4-(1-Ethyl-1H-1,3-benzimidazol-2-yl)-N,N- diphenylaniline monohydrate top

Crystal data top

C₂₇H₂₃N₃·H₂O	F(000) = 864
M_r = 407.50	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.090P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
4024 reflections	Δρ_max = 0.18 e Å⁻³
281 parameters	Δρ_min = −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)

Crystal data top

C₂₇H₂₃N₃·H₂O	V = 2195.0 (8) Å³
M_r = 407.50	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.278 (3) Å	µ = 0.08 mm⁻¹
b = 9.2690 (19) Å	T = 293 K
c = 19.468 (4) Å	0.30 × 0.20 × 0.10 mm
β = 97.81 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2487 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.025
T_min = 0.978, T_max = 0.992	3 standard reflections every 200 reflections
4223 measured reflections	intensity decay: 1%
4024 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.169	H-atom parameters constrained
S = 1.01	Δρ_max = 0.18 e Å⁻³
4024 reflections	Δρ_min = −0.26 e Å⁻³
281 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₃N₃·H₂O
M_r	407.50
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.278 (3), 9.2690 (19), 19.468 (4)
β (°)	97.81 (3)
V (Å³)	2195.0 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.978, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	4223, 4024, 2487
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.169, 1.01
No. of reflections	4024
No. of parameters	281
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.26

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x, y−1, z.

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Kakimoto, M., Ge, Z. Y., Hayakawa, T., Ando, S. & Ueda, M. (2008). Adv. Funct. Mater. 18, 584–590. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vinodkumar, R., Vaidya, S. D., Kumar, B. V. S., Bhise, U. N. & Mashelkar, U. C. (2008). ARKIVOC, 14, 37–49. CrossRef Google Scholar