2-Eth­oxy-6-{[1-(3-eth­oxy-2-hy­droxy­benz­yl)-1H-benzimidazol-2-yl]meth­yl}phenol nitro­methane monosolvate

Ha, K.

doi:10.1107/S1600536812023665

organic compounds

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Volume 68| Part 6| June 2012| Page o1914

doi:10.1107/S1600536812023665

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2-Ethoxy-6-{[1-(3-ethoxy-2-hydroxybenzyl)-1H-benzimidazol-2-yl]methyl}phenol nitromethane monosolvate

Kwang Ha ^a ^*

^aSchool of Applied Chemical Engineering, The Research Institute of Catalysis, Chonnam National University, Gwangju 500-757, Republic of Korea
^*Correspondence e-mail: hakwang@chonnam.ac.kr

(Received 23 May 2012; accepted 24 May 2012; online 31 May 2012)

In the title solvate, C₂₄H₂₄N₂O₄·CH₃NO₂, the benzene ring of the 2-ethoxy-6-methylphenol substituent is approximately perpendicular to the nearly planar benzimidazole ring [maximum deviation = 0.021 (2) Å], making a dihedral angle of 84.32 (7)°. The benzene ring of the 2-ethoxyphenol group is somewhat inclined to the benzimidazole ring plane by 28.03 (5)°. The dihedral angle between the benzene rings is 82.20 (9)°. The compound reveals strong intramolecular O—H⋯N and O—H⋯O hydrogen bonds, forming six- and five-membered rings, respectively. In the crystal, molecules are connected by bifurcated O—H⋯(O,O) hydrogen bonds, forming chains along the b axis.

Related literature

For the crystal structure of the methoxy derivative of the title compound, see: Al-Douh et al. (2009 ). For the crystal structure of the title compound as an acetonitrile monosolvate, see: Ha (2012 ).

Experimental

Crystal data

C₂₄H₂₄N₂O₄·CH₃NO₂
M_r = 465.50
Monoclinic, P 2₁ /c
a = 7.5151 (7) Å
b = 19.6463 (17) Å
c = 16.2578 (15) Å
β = 99.898 (2)°
V = 2364.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 273 K
0.36 × 0.20 × 0.13 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.856, T_max = 1.000
17462 measured reflections
5846 independent reflections
2523 reflections with I > 2σ(I)
R_int = 0.090

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.157
S = 0.95
5846 reflections
318 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N1	0.92 (4)	1.75 (4)	2.596 (3)	152 (3)
O3—H3O⋯O4	0.99 (3)	2.27 (3)	2.710 (2)	106 (2)
O3—H3O⋯O1ⁱ	0.99 (3)	1.91 (3)	2.819 (2)	151 (2)
O3—H3O⋯O2ⁱ	0.99 (3)	2.36 (3)	3.012 (3)	122 (2)
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812023665/tk5103sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812023665/tk5103Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812023665/tk5103Isup3.cml

checkCIF report

Comment top

The crystal structures of the related compound, 2-[1-(2-hydroxy-3-methoxybenzyl)-1H-benzimidazol-2-yl]-6-methoxyphenol monohydrate, and the title compound as an acetonitrile monosolvate have been reported previously (Al-Douh et al., 2009; Ha, 2012).

The title compound, C₂₄H₂₄N₂O₄.CH₃NO₂, contains a disubstituted benzimidazole molecule and a lattice solvent molecule (Fig. 1). The benzene ring (C17–C22) of the 2-ethoxy-6-methylphenol substituent is approximately perpendicular to the nearly planar benzimidazole ring system [maximum deviation = 0.021 (2) Å], making a dihedral angle of 84.32 (7)°. The benzene ring (C8–C13) of the 2-ethoxyphenol group is somewhat inclined to the benzimidazole ring plane by 28.03 (5)°. The dihedral angle between the benzene rings is 82.20 (9)°. The compound reveals strong intramolecular O—H···N and O—H···O hydrogen bonds, forming six- and five-membered rings, respectively (Fig. 2 and Table 1). In the crystal, molecules are connected by bifurcated O—H···(O,O) hydrogen bonds, forming chains along the b axis (Fig. 2 and Table 1).

Related literature top

For the crystal structure of the methoxy derivative of the title compound, see: Al-Douh et al. (2009). For the crystal structure of the title compound as an acetonitrile monosolvate, see: Ha (2012).

Experimental top

1,2-Phenylenediamine (0.7568 g, 6.998 mmol) and 3-ethoxysalicylaldehyde (2.3269 g, 14.003 mmol) in EtOH (20 ml) were stirred for 5 h at room temperature. After evaporation of the solvent, the residue was recrystallized from a mixture of acetone and ether at 188 K, to give an orange powder (1.9139 g). Crystals suitable for X-ray analysis were obtained by slow evaporation from its CH₃NO₂ solution at room temperature.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A structure detail of the title compound, with atom numbering. Displacement ellipsoids are drawn at the 40% probability level for non-H atoms.
	Fig. 2. A partial view along the a axis of the crystal packing of the title compound. Intra- and intermolecular O—H···N and O—H···O hydrogen-bonds are shown as dashed lines.

2-Ethoxy-6-{[1-(3-ethoxy-2-hydroxybenzyl)-1H-benzimidazol- 2-yl]methyl}phenol nitromethane monosolvate top

Crystal data top

C₂₄H₂₄N₂O₄·CH₃NO₂	F(000) = 984
M_r = 465.50	D_x = 1.308 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2443 reflections
a = 7.5151 (7) Å	θ = 2.8–22.7°
b = 19.6463 (17) Å	µ = 0.09 mm⁻¹
c = 16.2578 (15) Å	T = 273 K
β = 99.898 (2)°	Block, orange
V = 2364.6 (4) Å³	0.36 × 0.20 × 0.13 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD diffractometer	5846 independent reflections
Radiation source: fine-focus sealed tube	2523 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.090
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→10
T_min = 0.856, T_max = 1.000	k = −26→23
17462 measured reflections	l = −21→21

Refinement top

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ²(F_o²) + (0.0503P)²] where P = (F_o² + 2F_c²)/3
5846 reflections	(Δ/σ)_max < 0.001
318 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₄H₂₄N₂O₄·CH₃NO₂	V = 2364.6 (4) Å³
M_r = 465.50	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.5151 (7) Å	µ = 0.09 mm⁻¹
b = 19.6463 (17) Å	T = 273 K
c = 16.2578 (15) Å	0.36 × 0.20 × 0.13 mm
β = 99.898 (2)°

Data collection top

Bruker SMART 1000 CCD diffractometer	5846 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2523 reflections with I > 2σ(I)
T_min = 0.856, T_max = 1.000	R_int = 0.090
17462 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	Δρ_max = 0.29 e Å⁻³
5846 reflections	Δρ_min = −0.22 e Å⁻³
318 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
O1	0.1517 (3)	−0.00824 (8)	0.25918 (12)	0.0364 (5)
H1O	0.166 (5)	0.0034 (17)	0.206 (2)	0.105 (14)*
O2	0.1909 (3)	−0.02200 (9)	0.41939 (11)	0.0421 (5)
O3	−0.0023 (2)	0.36913 (9)	0.19378 (11)	0.0367 (5)
H3O	−0.032 (4)	0.4180 (15)	0.1965 (19)	0.076 (10)*
O4	0.2353 (2)	0.47405 (8)	0.21047 (12)	0.0399 (5)
N1	0.2058 (3)	0.06287 (10)	0.13119 (14)	0.0362 (6)
N2	0.1347 (3)	0.17347 (10)	0.13095 (13)	0.0329 (6)
C1	0.1707 (4)	0.08554 (13)	0.04930 (17)	0.0352 (7)
C2	0.1729 (4)	0.05148 (14)	−0.02530 (18)	0.0424 (8)
H2	0.2012	0.0054	−0.0258	0.051*
C3	0.1320 (4)	0.08766 (15)	−0.09819 (18)	0.0475 (8)
H3	0.1329	0.0657	−0.1488	0.057*
C4	0.0889 (4)	0.15692 (15)	−0.09826 (19)	0.0494 (8)
H4	0.0629	0.1801	−0.1488	0.059*
C5	0.0841 (4)	0.19139 (14)	−0.02510 (19)	0.0453 (8)
H5	0.0545	0.2373	−0.0249	0.054*
C6	0.1256 (4)	0.15445 (13)	0.04832 (17)	0.0345 (7)
C7	0.1872 (3)	0.11683 (12)	0.17827 (16)	0.0312 (6)
C8	0.2174 (3)	0.11250 (12)	0.26941 (16)	0.0311 (6)
C9	0.1955 (3)	0.04905 (12)	0.30544 (16)	0.0298 (6)
C10	0.2224 (4)	0.04219 (13)	0.39271 (17)	0.0336 (7)
C11	0.2786 (4)	0.09698 (14)	0.44263 (18)	0.0403 (7)
H11	0.2974	0.0924	0.5004	0.048*
C12	0.3074 (4)	0.15947 (14)	0.40681 (18)	0.0433 (8)
H12	0.3477	0.1963	0.4409	0.052*
C13	0.2772 (4)	0.16734 (13)	0.32187 (18)	0.0396 (7)
H13	0.2965	0.2095	0.2989	0.048*
C14	0.2320 (4)	−0.03579 (14)	0.50701 (17)	0.0444 (8)
H14A	0.1562	−0.0085	0.5368	0.053*
H14B	0.3574	−0.0251	0.5285	0.053*
C15	0.1970 (4)	−0.11004 (14)	0.51828 (18)	0.0537 (9)
H15A	0.0730	−0.1201	0.4961	0.080*
H15B	0.2216	−0.1211	0.5766	0.080*
H15C	0.2741	−0.1365	0.4893	0.080*
C16	0.0750 (4)	0.23959 (12)	0.15603 (17)	0.0355 (7)
H16A	0.0374	0.2351	0.2099	0.043*
H16B	−0.0293	0.2539	0.1161	0.043*
C17	0.2187 (4)	0.29402 (12)	0.16189 (16)	0.0323 (7)
C18	0.1706 (4)	0.35914 (12)	0.18154 (16)	0.0313 (6)
C19	0.2982 (4)	0.41196 (13)	0.18991 (16)	0.0335 (6)
C20	0.4725 (4)	0.39823 (14)	0.17722 (17)	0.0408 (7)
H20	0.5579	0.4329	0.1821	0.049*
C21	0.5192 (4)	0.33281 (14)	0.15726 (18)	0.0455 (8)
H21	0.6363	0.3236	0.1491	0.055*
C22	0.3929 (4)	0.28132 (13)	0.14944 (18)	0.0414 (7)
H22	0.4252	0.2376	0.1357	0.050*
C23	0.3662 (4)	0.52643 (13)	0.2358 (2)	0.0467 (8)
H23A	0.4226	0.5401	0.1890	0.056*
H23B	0.4595	0.5098	0.2799	0.056*
C24	0.2705 (4)	0.58586 (14)	0.2663 (2)	0.0598 (10)
H24A	0.1764	0.6012	0.2226	0.090*
H24B	0.3550	0.6222	0.2820	0.090*
H24C	0.2187	0.5723	0.3138	0.090*
O5	0.6407 (5)	0.27813 (18)	0.4851 (3)	0.1619 (18)
O6	0.6611 (6)	0.3759 (2)	0.5301 (2)	0.1664 (18)
N3	0.6350 (4)	0.3364 (2)	0.4748 (3)	0.0808 (10)
C25	0.6008 (6)	0.3659 (3)	0.3918 (3)	0.133 (2)
H25A	0.4821	0.3856	0.3815	0.200*
H25B	0.6087	0.3311	0.3511	0.200*
H25C	0.6889	0.4006	0.3877	0.200*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0477 (13)	0.0267 (10)	0.0354 (12)	−0.0027 (8)	0.0084 (10)	−0.0019 (9)
O2	0.0549 (14)	0.0404 (11)	0.0313 (11)	0.0011 (9)	0.0082 (10)	0.0044 (9)
O3	0.0338 (12)	0.0312 (11)	0.0459 (12)	0.0002 (8)	0.0094 (10)	−0.0025 (9)
O4	0.0400 (13)	0.0298 (10)	0.0509 (13)	−0.0062 (9)	0.0106 (10)	−0.0049 (9)
N1	0.0440 (16)	0.0308 (12)	0.0345 (14)	0.0011 (10)	0.0083 (12)	−0.0006 (11)
N2	0.0409 (15)	0.0252 (12)	0.0327 (14)	0.0009 (10)	0.0070 (11)	−0.0007 (10)
C1	0.0424 (18)	0.0322 (15)	0.0321 (16)	−0.0024 (13)	0.0100 (14)	−0.0017 (13)
C2	0.050 (2)	0.0393 (16)	0.0385 (19)	−0.0033 (14)	0.0103 (15)	−0.0039 (14)
C3	0.056 (2)	0.056 (2)	0.0324 (18)	−0.0049 (16)	0.0112 (16)	−0.0025 (15)
C4	0.062 (2)	0.051 (2)	0.0354 (19)	−0.0020 (16)	0.0086 (16)	0.0086 (16)
C5	0.056 (2)	0.0380 (17)	0.042 (2)	0.0000 (14)	0.0088 (16)	0.0043 (15)
C6	0.0391 (18)	0.0341 (16)	0.0310 (16)	−0.0049 (12)	0.0076 (13)	0.0013 (13)
C7	0.0301 (16)	0.0298 (14)	0.0338 (16)	−0.0002 (12)	0.0055 (13)	−0.0008 (13)
C8	0.0299 (16)	0.0268 (14)	0.0360 (16)	0.0012 (11)	0.0045 (13)	−0.0028 (12)
C9	0.0280 (16)	0.0285 (14)	0.0326 (16)	0.0019 (11)	0.0047 (12)	−0.0041 (12)
C10	0.0323 (17)	0.0324 (15)	0.0366 (18)	0.0021 (12)	0.0070 (13)	0.0027 (13)
C11	0.0438 (19)	0.0438 (17)	0.0326 (16)	0.0002 (14)	0.0044 (14)	−0.0019 (14)
C12	0.048 (2)	0.0406 (17)	0.0402 (19)	−0.0014 (14)	0.0052 (15)	−0.0089 (14)
C13	0.0437 (19)	0.0324 (16)	0.0424 (19)	−0.0016 (13)	0.0065 (15)	−0.0027 (13)
C14	0.047 (2)	0.0526 (19)	0.0332 (18)	0.0012 (14)	0.0060 (15)	0.0065 (14)
C15	0.067 (2)	0.053 (2)	0.0408 (19)	0.0023 (16)	0.0111 (17)	0.0124 (15)
C16	0.0391 (18)	0.0275 (14)	0.0405 (17)	0.0010 (12)	0.0088 (14)	−0.0017 (12)
C17	0.0357 (18)	0.0303 (14)	0.0314 (16)	0.0014 (12)	0.0071 (13)	0.0018 (12)
C18	0.0308 (17)	0.0352 (15)	0.0271 (15)	−0.0006 (12)	0.0028 (12)	0.0027 (12)
C19	0.0369 (18)	0.0338 (15)	0.0291 (16)	−0.0024 (13)	0.0041 (13)	0.0001 (12)
C20	0.0394 (19)	0.0452 (17)	0.0384 (17)	−0.0081 (14)	0.0080 (14)	0.0010 (14)
C21	0.0402 (19)	0.0466 (18)	0.052 (2)	0.0019 (15)	0.0148 (16)	−0.0008 (15)
C22	0.043 (2)	0.0357 (16)	0.0463 (19)	0.0018 (14)	0.0101 (15)	−0.0004 (13)
C23	0.042 (2)	0.0415 (17)	0.055 (2)	−0.0142 (14)	0.0040 (16)	−0.0075 (15)
C24	0.059 (2)	0.0447 (19)	0.077 (3)	−0.0144 (16)	0.016 (2)	−0.0212 (17)
O5	0.123 (3)	0.078 (2)	0.279 (5)	−0.026 (2)	0.018 (3)	0.051 (3)
O6	0.212 (5)	0.166 (4)	0.118 (3)	−0.030 (3)	0.021 (3)	−0.050 (3)
N3	0.067 (2)	0.074 (3)	0.098 (3)	−0.0158 (19)	0.006 (2)	0.000 (2)
C25	0.085 (4)	0.232 (6)	0.083 (4)	0.034 (4)	0.017 (3)	0.060 (4)

Geometric parameters (Å, º) top

O1—C9	1.362 (3)	C13—H13	0.9300
O1—H1O	0.92 (4)	C14—C15	1.499 (4)
O2—C10	1.367 (3)	C14—H14A	0.9700
O2—C14	1.431 (3)	C14—H14B	0.9700
O3—C18	1.362 (3)	C15—H15A	0.9600
O3—H3O	0.99 (3)	C15—H15B	0.9600
O4—C19	1.370 (3)	C15—H15C	0.9600
O4—C23	1.434 (3)	C16—C17	1.511 (3)
N1—C7	1.329 (3)	C16—H16A	0.9700
N1—C1	1.386 (3)	C16—H16B	0.9700
N2—C7	1.372 (3)	C17—C22	1.381 (4)
N2—C6	1.385 (3)	C17—C18	1.382 (3)
N2—C16	1.455 (3)	C18—C19	1.403 (3)
C1—C2	1.388 (4)	C19—C20	1.387 (4)
C1—C6	1.395 (3)	C20—C21	1.385 (3)
C2—C3	1.371 (4)	C20—H20	0.9300
C2—H2	0.9300	C21—C22	1.378 (4)
C3—C4	1.399 (4)	C21—H21	0.9300
C3—H3	0.9300	C22—H22	0.9300
C4—C5	1.374 (4)	C23—C24	1.500 (4)
C4—H4	0.9300	C23—H23A	0.9700
C5—C6	1.386 (4)	C23—H23B	0.9700
C5—H5	0.9300	C24—H24A	0.9600
C7—C8	1.462 (4)	C24—H24B	0.9600
C8—C9	1.399 (3)	C24—H24C	0.9600
C8—C13	1.399 (3)	O5—N3	1.157 (4)
C9—C10	1.405 (3)	O6—N3	1.178 (4)
C10—C11	1.370 (3)	N3—C25	1.450 (5)
C11—C12	1.392 (3)	C25—H25A	0.9600
C11—H11	0.9300	C25—H25B	0.9600
C12—C13	1.369 (4)	C25—H25C	0.9600
C12—H12	0.9300

C9—O1—H1O	105 (2)	H14A—C14—H14B	108.6
C10—O2—C14	118.1 (2)	C14—C15—H15A	109.5
C18—O3—H3O	112.0 (18)	C14—C15—H15B	109.5
C19—O4—C23	117.4 (2)	H15A—C15—H15B	109.5
C7—N1—C1	106.0 (2)	C14—C15—H15C	109.5
C7—N2—C6	106.7 (2)	H15A—C15—H15C	109.5
C7—N2—C16	129.8 (2)	H15B—C15—H15C	109.5
C6—N2—C16	123.1 (2)	N2—C16—C17	113.5 (2)
N1—C1—C2	131.0 (2)	N2—C16—H16A	108.9
N1—C1—C6	109.2 (2)	C17—C16—H16A	108.9
C2—C1—C6	119.8 (3)	N2—C16—H16B	108.9
C3—C2—C1	118.1 (3)	C17—C16—H16B	108.9
C3—C2—H2	121.0	H16A—C16—H16B	107.7
C1—C2—H2	121.0	C22—C17—C18	119.5 (2)
C2—C3—C4	121.5 (3)	C22—C17—C16	123.2 (2)
C2—C3—H3	119.2	C18—C17—C16	117.2 (2)
C4—C3—H3	119.2	O3—C18—C17	117.4 (2)
C5—C4—C3	121.3 (3)	O3—C18—C19	122.2 (2)
C5—C4—H4	119.4	C17—C18—C19	120.4 (2)
C3—C4—H4	119.4	O4—C19—C20	125.7 (2)
C4—C5—C6	116.9 (3)	O4—C19—C18	115.1 (2)
C4—C5—H5	121.6	C20—C19—C18	119.2 (2)
C6—C5—H5	121.6	C21—C20—C19	119.9 (3)
N2—C6—C5	131.3 (2)	C21—C20—H20	120.0
N2—C6—C1	106.2 (2)	C19—C20—H20	120.0
C5—C6—C1	122.4 (3)	C22—C21—C20	120.3 (3)
N1—C7—N2	111.9 (2)	C22—C21—H21	119.8
N1—C7—C8	121.6 (2)	C20—C21—H21	119.8
N2—C7—C8	126.5 (2)	C21—C22—C17	120.6 (2)
C9—C8—C13	118.6 (2)	C21—C22—H22	119.7
C9—C8—C7	117.8 (2)	C17—C22—H22	119.7
C13—C8—C7	123.4 (2)	O4—C23—C24	108.0 (2)
O1—C9—C8	122.7 (2)	O4—C23—H23A	110.1
O1—C9—C10	117.2 (2)	C24—C23—H23A	110.1
C8—C9—C10	120.1 (2)	O4—C23—H23B	110.1
O2—C10—C11	126.1 (2)	C24—C23—H23B	110.1
O2—C10—C9	114.0 (2)	H23A—C23—H23B	108.4
C11—C10—C9	119.9 (2)	C23—C24—H24A	109.5
C10—C11—C12	120.0 (3)	C23—C24—H24B	109.5
C10—C11—H11	120.0	H24A—C24—H24B	109.5
C12—C11—H11	120.0	C23—C24—H24C	109.5
C13—C12—C11	120.7 (3)	H24A—C24—H24C	109.5
C13—C12—H12	119.6	H24B—C24—H24C	109.5
C11—C12—H12	119.6	O5—N3—O6	123.0 (5)
C12—C13—C8	120.5 (3)	O5—N3—C25	121.8 (5)
C12—C13—H13	119.7	O6—N3—C25	115.2 (4)
C8—C13—H13	119.7	N3—C25—H25A	109.5
O2—C14—C15	107.1 (2)	N3—C25—H25B	109.5
O2—C14—H14A	110.3	H25A—C25—H25B	109.5
C15—C14—H14A	110.3	N3—C25—H25C	109.5
O2—C14—H14B	110.3	H25A—C25—H25C	109.5
C15—C14—H14B	110.3	H25B—C25—H25C	109.5

C7—N1—C1—C2	179.1 (3)	O1—C9—C10—O2	−3.3 (3)
C7—N1—C1—C6	−1.6 (3)	C8—C9—C10—O2	178.0 (2)
N1—C1—C2—C3	−179.9 (3)	O1—C9—C10—C11	175.6 (2)
C6—C1—C2—C3	0.8 (4)	C8—C9—C10—C11	−3.1 (4)
C1—C2—C3—C4	−0.1 (4)	O2—C10—C11—C12	179.3 (2)
C2—C3—C4—C5	−0.6 (5)	C9—C10—C11—C12	0.5 (4)
C3—C4—C5—C6	0.6 (4)	C10—C11—C12—C13	1.2 (4)
C7—N2—C6—C5	−178.3 (3)	C11—C12—C13—C8	−0.3 (4)
C16—N2—C6—C5	8.6 (4)	C9—C8—C13—C12	−2.2 (4)
C7—N2—C6—C1	1.0 (3)	C7—C8—C13—C12	−178.3 (3)
C16—N2—C6—C1	−172.1 (2)	C10—O2—C14—C15	−176.3 (2)
C4—C5—C6—N2	179.4 (3)	C7—N2—C16—C17	102.3 (3)
C4—C5—C6—C1	0.2 (4)	C6—N2—C16—C17	−86.3 (3)
N1—C1—C6—N2	0.3 (3)	N2—C16—C17—C22	−3.6 (4)
C2—C1—C6—N2	179.8 (2)	N2—C16—C17—C18	177.0 (2)
N1—C1—C6—C5	179.7 (3)	C22—C17—C18—O3	−179.6 (2)
C2—C1—C6—C5	−0.9 (4)	C16—C17—C18—O3	−0.2 (4)
C1—N1—C7—N2	2.3 (3)	C22—C17—C18—C19	−0.8 (4)
C1—N1—C7—C8	−178.9 (2)	C16—C17—C18—C19	178.6 (2)
C6—N2—C7—N1	−2.1 (3)	C23—O4—C19—C20	−12.0 (4)
C16—N2—C7—N1	170.3 (2)	C23—O4—C19—C18	168.1 (2)
C6—N2—C7—C8	179.1 (2)	O3—C18—C19—O4	−0.6 (4)
C16—N2—C7—C8	−8.4 (4)	C17—C18—C19—O4	−179.2 (2)
N1—C7—C8—C9	−25.1 (4)	O3—C18—C19—C20	179.5 (2)
N2—C7—C8—C9	153.6 (2)	C17—C18—C19—C20	0.8 (4)
N1—C7—C8—C13	151.1 (3)	O4—C19—C20—C21	179.5 (3)
N2—C7—C8—C13	−30.3 (4)	C18—C19—C20—C21	−0.6 (4)
C13—C8—C9—O1	−174.7 (2)	C19—C20—C21—C22	0.4 (4)
C7—C8—C9—O1	1.6 (4)	C20—C21—C22—C17	−0.4 (4)
C13—C8—C9—C10	3.9 (4)	C18—C17—C22—C21	0.6 (4)
C7—C8—C9—C10	−179.8 (2)	C16—C17—C22—C21	−178.7 (3)
C14—O2—C10—C11	−4.9 (4)	C19—O4—C23—C24	−172.3 (2)
C14—O2—C10—C9	173.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1	0.92 (4)	1.75 (4)	2.596 (3)	152 (3)
O3—H3O···O4	0.99 (3)	2.27 (3)	2.710 (2)	106 (2)
O3—H3O···O1ⁱ	0.99 (3)	1.91 (3)	2.819 (2)	151 (2)
O3—H3O···O2ⁱ	0.99 (3)	2.36 (3)	3.012 (3)	122 (2)

Symmetry code: (i) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₄N₂O₄·CH₃NO₂
M_r	465.50
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	7.5151 (7), 19.6463 (17), 16.2578 (15)
β (°)	99.898 (2)
V (Å³)	2364.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.36 × 0.20 × 0.13

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.856, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	17462, 5846, 2523
R_int	0.090
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.157, 0.95
No. of reflections	5846
No. of parameters	318
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.22

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1	0.92 (4)	1.75 (4)	2.596 (3)	152 (3)
O3—H3O···O4	0.99 (3)	2.27 (3)	2.710 (2)	106 (2)
O3—H3O···O1ⁱ	0.99 (3)	1.91 (3)	2.819 (2)	151 (2)
O3—H3O···O2ⁱ	0.99 (3)	2.36 (3)	3.012 (3)	122 (2)

Symmetry code: (i) −x, y+1/2, −z+1/2.

Acknowledgements

This work was supported by the Priority Research Centers Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2011–0030747).

References

Al-Douh, M. H., Osman, H., Hamid, S. A., Kia, R. & Fun, H.-K. (2009). Acta Cryst. E65, o913–o914. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Ha, K. (2012). Acta Cryst. E68, o1398. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 6| June 2012| Page o1914

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-Eth­­oxy-6-{[1-(3-eth­­oxy-2-hy­dr­oxy­benz­yl)-1H-benzimidazol-2-yl]meth­yl}phenol nitro­methane monosolvate

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Experimental

Crystal data

Data collection

Refinement

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References

organic compounds

2-Ethoxy-6-{[1-(3-ethoxy-2-hydroxybenzyl)-1H-benzimidazol-2-yl]methyl}phenol nitromethane monosolvate