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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 4| April 2009| Pages o925-o926

2-[1-(2-Hydr­­oxy-3-meth­oxy­benz­yl)-1H-benzimidazol-2-yl]-6-meth­oxy­phenol methanol 1.13-solvate

aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bKulliyyah of Science, International Islamic University Malaysia (IIUM), Jalan Istana, Bandar Indera Mahkota 25200 Kuantan, Pahang, Malaysia, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my

(Received 19 March 2009; accepted 26 March 2009; online 31 March 2009)

In the main mol­ecule of the title compound, C22H20N2O4·1.13CH4O, the dihedral angles between the benzimidazole plane and the two benzene rings are 80.53 (10) and 82.76 (10)°. The solvent mol­ecules are disordered between three positions, with refined occupancies of 0.506 (13), 0.373 (13) and 0.249 (5). The crystal structure is stabilized by inter­molecular O—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds. The crystal studied was a merohedral twin [BASF ratio of 0.917 (1)/0.083 (1)].

Related literature

For related structures, see Al-Douh et al. (2006[Al-Douh, M. H., Hamid, S. A., Osman, H., Ng, S.-L. & Fun, H.-K. (2006). Acta Cryst. E62, o3954-o3956.], 2009[Al-Douh, M. H., Osman, H., Hamid, S. A., Kia, R. & Fun, H.-K. (2009). Acta Cryst. E65, o913-o914.]). For hydrogen-bond motifs, see Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chamg, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C22H20N2O4·1.13CH4O

  • Mr = 412.53

  • Monoclinic, P 21 /n

  • a = 7.2451 (1) Å

  • b = 11.1482 (2) Å

  • c = 26.2046 (5) Å

  • β = 90.010 (1)°

  • V = 2116.54 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 100 K

  • 0.27 × 0.15 × 0.13 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.976, Tmax = 0.988

  • 18918 measured reflections

  • 3940 independent reflections

  • 3099 reflections with I > 2σ(I)

  • Rint = 0.040

Refinement
  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.122

  • S = 1.09

  • 3940 reflections

  • 317 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H3⋯O5Ai 0.82 1.85 2.626 (5) 157
O5A—H5A1⋯N1ii 0.82 2.07 2.842 (5) 157
O1—H1⋯O3iii 0.82 2.19 2.956 (2) 155
C14—H14B⋯O2iii 0.97 2.46 3.335 (3) 150
C23A—H23B⋯O5Aiv 0.96 2.57 3.215 (16) 125
Symmetry codes: (i) x-1, y-1, z; (ii) x+1, y, z; (iii) -x, -y, -z; (iv) -x+2, -y+1, -z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

In continuation of our crystallographic study of benzimidazole derivatives (Al-Douh et al., 2006, 2009), we present here the crystal structure of the title compound, (I).

In the title compound (Fig. 1), intramolecular O—H···O hydrogen bonds (Table 1) generate five-membered rings with S(5) ring motifs (Bernstein et al., 1995). The dihedral angle between the two outer benzene rings is 75.18 (12)°. The benzimidazole plane and two outer benzene rings form dihedral angles 80.53 (10) and 82.76 (10)°, respectively. There are short intermolecular contacts C16···C21vi of 3.209 (4) Å and C17···C21vi of 3.308 (4) Å [symmetry code: (vi) 1 - x, -y, -z].

The crystal structure is stabilized by intermolecular O—H···O, O—H···N and C—H···O hydrogen bonds (Table 1).

Related literature top

For related crystal structures, see Al-Douh et al. (2006, 2009). For details on hydrogen-bond motifs, see Bernstein et al. (1995). For stability of the temperature controller used for data collection, see: Cosier & Glazer (1986).

Experimental top

A 100-mL, three-necked, round-bottomed flask is equipped with a nitrogen inlet adapter, rubber septum, glass stopper, and a magnetic stirring bar. The flask is charged with 5 mL of dichloromethane and (608.61 mg, 0.004 mol) of o-vanillin, and then is cooled in an ice-water bath while a solution of (216.29 mg, 0.002 mol) of o-phenylenediamine in 5 mL of dichloromethane is added dropwise via syringe over 15 min. After 30 min, 10 g of anhydrous magnesium sulfate is added in one portion. The ice-water bath is removed, and the reaction mixture is stirred at room temperature for 2hr. The resulting solution is allowed to cool to room temperature and then is cooled in an ice-water bath for 2 hr. Filtration provides the light yellowish powder. The single crystals suitable for X-ray diffraction were obtained by evaporation of methanol and dichloromethane (7:3) solvent at room temperature.

Refinement top

All H atoms were geometrically positioned (C—H 0.93–0.97 Å, O—H 0.82 Å) and refined in a riding model approximation, with Uiso(H) = 1.2 or 1.5 (C, O). The methanol solvent molecules were treated as disordered over three positions with refined site-occupancies of 0.506 (13), 0.373 (13) and 0.249 (5) with SUMP command equal to 1.0 (1). The crystal studied was a twin with the refined BASF ratio of 0.917 (1)/0.083 (1). During the data collection, the temperature was controlled according to the literature procedure (Cosier & Glazer, 1986).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering. The disordered methanol solvent molecules were omitted for clarity. Intramolecular hydrogen bonds are drawn as dashed lines.
2-[1-(2-Hydroxy-3-methoxybenzyl)-1H-benzimidazol-2-yl]-6-methoxyphenol methanol 1.13-solvate top
Crystal data top
C22H20N2O4·1.13CH4OF(000) = 873
Mr = 412.53Dx = 1.295 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4846 reflections
a = 7.2451 (1) Åθ = 2.9–26.4°
b = 11.1482 (2) ŵ = 0.09 mm1
c = 26.2046 (5) ÅT = 100 K
β = 90.010 (1)°Block, colourless
V = 2116.54 (6) Å30.27 × 0.15 × 0.13 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
3940 independent reflections
Radiation source: fine-focus sealed tube3099 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
ϕ and ω scansθmax = 25.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 88
Tmin = 0.976, Tmax = 0.988k = 1213
18918 measured reflectionsl = 3128
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0415P)2 + 1.5448P]
where P = (Fo2 + 2Fc2)/3
3940 reflections(Δ/σ)max < 0.001
317 parametersΔρmax = 0.28 e Å3
1 restraintΔρmin = 0.23 e Å3
Crystal data top
C22H20N2O4·1.13CH4OV = 2116.54 (6) Å3
Mr = 412.53Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.2451 (1) ŵ = 0.09 mm1
b = 11.1482 (2) ÅT = 100 K
c = 26.2046 (5) Å0.27 × 0.15 × 0.13 mm
β = 90.010 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
3940 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
3099 reflections with I > 2σ(I)
Tmin = 0.976, Tmax = 0.988Rint = 0.040
18918 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0501 restraint
wR(F2) = 0.122H-atom parameters constrained
S = 1.09Δρmax = 0.28 e Å3
3940 reflectionsΔρmin = 0.23 e Å3
317 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.0363 (2)0.18739 (17)0.00815 (6)0.0272 (4)
H10.03850.18910.02310.041*
O20.3146 (2)0.15819 (18)0.05634 (6)0.0346 (5)
O30.0521 (3)0.24674 (15)0.09905 (6)0.0282 (4)
H30.06640.31960.09710.042*
O40.2424 (3)0.39894 (16)0.15953 (8)0.0437 (6)
N10.0259 (3)0.31698 (18)0.13518 (7)0.0220 (5)
N20.0044 (3)0.11719 (17)0.13178 (7)0.0196 (5)
C10.1122 (3)0.2812 (2)0.16904 (9)0.0199 (5)
C20.2243 (3)0.3492 (2)0.20124 (9)0.0237 (6)
H2A0.21610.43240.20190.028*
C30.3483 (3)0.2886 (2)0.23220 (9)0.0253 (6)
H3A0.42320.33210.25430.030*
C40.3634 (4)0.1640 (2)0.23092 (9)0.0255 (6)
H4A0.44790.12640.25230.031*
C50.2560 (3)0.0947 (2)0.19875 (9)0.0229 (6)
H5A0.26660.01160.19770.027*
C60.1313 (3)0.1562 (2)0.16799 (8)0.0195 (5)
C70.0860 (3)0.2171 (2)0.11421 (9)0.0198 (5)
C80.2427 (3)0.2062 (2)0.07811 (9)0.0196 (5)
C90.2130 (3)0.1894 (2)0.02649 (9)0.0202 (5)
C100.3634 (4)0.1738 (2)0.00633 (9)0.0233 (6)
C110.5417 (4)0.1767 (2)0.01214 (10)0.0289 (6)
H11A0.64110.16650.00990.035*
C120.5715 (4)0.1951 (3)0.06398 (10)0.0324 (7)
H12A0.69130.19810.07660.039*
C130.4233 (3)0.2090 (2)0.09689 (10)0.0281 (6)
H13A0.44410.22030.13160.034*
C140.0209 (3)0.0061 (2)0.11471 (9)0.0203 (5)
H14A0.08400.00540.08210.024*
H14B0.09940.04230.10950.024*
C150.1298 (3)0.0828 (2)0.15162 (9)0.0193 (5)
C160.1386 (3)0.2048 (2)0.14165 (9)0.0210 (5)
C170.2424 (4)0.2802 (2)0.17332 (10)0.0256 (6)
C180.3361 (4)0.2327 (2)0.21462 (10)0.0267 (6)
H18A0.40480.28250.23580.032*
C190.3274 (3)0.1111 (2)0.22427 (10)0.0263 (6)
H19A0.39060.07930.25200.032*
C200.2259 (3)0.0364 (2)0.19313 (9)0.0241 (6)
H20A0.22170.04540.19990.029*
C210.4624 (5)0.1568 (4)0.09260 (11)0.0588 (11)
H21A0.41260.15900.12650.088*
H21B0.53370.08490.08830.088*
H21C0.54000.22550.08730.088*
C220.4019 (4)0.4674 (3)0.17089 (12)0.0399 (7)
H22A0.50940.42610.15870.060*
H22B0.39310.54430.15460.060*
H22C0.41120.47830.20710.060*
O5A1.0245 (11)0.5263 (4)0.0733 (2)0.034 (2)0.506 (13)
H5A11.02850.48050.09780.051*0.506 (13)
C23A0.8593 (19)0.5039 (7)0.0444 (6)0.082 (5)0.506 (13)
H23A0.85270.42030.03580.123*0.506 (13)
H23B0.86160.55070.01360.123*0.506 (13)
H23C0.75340.52570.06430.123*0.506 (13)
O5B0.9164 (17)0.5416 (6)0.0975 (4)0.048 (4)0.373 (13)
H5B0.99970.49770.08740.072*0.373 (13)
C23B0.739 (3)0.5162 (11)0.0664 (4)0.064 (4)0.373 (13)
H23D0.76330.45470.04170.096*0.373 (13)
H23E0.70070.58810.04930.096*0.373 (13)
H23F0.64290.49000.08910.096*0.373 (13)
O5C0.718 (2)0.4931 (11)0.0088 (4)0.082 (4)0.249 (5)
H5C0.71380.48290.02220.123*0.249 (5)
C23C0.537 (3)0.5098 (15)0.0278 (8)0.092 (7)0.249 (5)
H23G0.45420.45690.01020.139*0.249 (5)
H23H0.54010.48940.06330.139*0.249 (5)
H23I0.49570.59110.02390.139*0.249 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0169 (9)0.0456 (11)0.0192 (9)0.0011 (8)0.0000 (7)0.0004 (8)
O20.0215 (10)0.0621 (13)0.0202 (9)0.0080 (9)0.0070 (8)0.0083 (9)
O30.0329 (10)0.0216 (9)0.0302 (10)0.0024 (8)0.0068 (8)0.0033 (7)
O40.0460 (13)0.0217 (10)0.0633 (14)0.0073 (9)0.0233 (11)0.0015 (9)
N10.0227 (11)0.0222 (11)0.0212 (10)0.0008 (9)0.0010 (9)0.0005 (9)
N20.0197 (11)0.0203 (11)0.0188 (10)0.0011 (9)0.0016 (9)0.0001 (8)
C10.0194 (12)0.0224 (13)0.0179 (11)0.0008 (10)0.0033 (10)0.0011 (10)
C20.0222 (13)0.0258 (14)0.0231 (13)0.0033 (11)0.0044 (11)0.0039 (11)
C30.0197 (13)0.0343 (15)0.0220 (12)0.0064 (12)0.0010 (11)0.0048 (11)
C40.0207 (13)0.0348 (15)0.0210 (12)0.0006 (12)0.0027 (11)0.0019 (11)
C50.0234 (13)0.0231 (13)0.0220 (12)0.0017 (11)0.0002 (11)0.0036 (10)
C60.0175 (12)0.0248 (13)0.0163 (11)0.0047 (11)0.0010 (10)0.0020 (10)
C70.0201 (13)0.0212 (13)0.0182 (11)0.0015 (11)0.0030 (10)0.0011 (10)
C80.0196 (12)0.0187 (12)0.0204 (12)0.0006 (10)0.0020 (10)0.0009 (10)
C90.0157 (12)0.0203 (13)0.0246 (12)0.0003 (10)0.0002 (10)0.0002 (10)
C100.0233 (13)0.0258 (14)0.0208 (12)0.0035 (11)0.0013 (11)0.0023 (10)
C110.0192 (13)0.0366 (16)0.0310 (14)0.0028 (12)0.0064 (11)0.0009 (12)
C120.0162 (13)0.0496 (18)0.0314 (15)0.0010 (13)0.0038 (12)0.0039 (13)
C130.0231 (14)0.0394 (16)0.0219 (13)0.0032 (12)0.0023 (11)0.0013 (12)
C140.0204 (12)0.0216 (13)0.0188 (12)0.0004 (11)0.0014 (10)0.0003 (10)
C150.0154 (12)0.0232 (13)0.0194 (12)0.0001 (10)0.0051 (10)0.0002 (10)
C160.0170 (12)0.0248 (13)0.0212 (12)0.0005 (11)0.0032 (10)0.0004 (10)
C170.0237 (13)0.0208 (13)0.0324 (14)0.0007 (11)0.0003 (12)0.0039 (11)
C180.0228 (14)0.0280 (15)0.0292 (14)0.0028 (12)0.0023 (12)0.0102 (11)
C190.0222 (14)0.0315 (15)0.0253 (13)0.0009 (12)0.0042 (11)0.0013 (11)
C200.0215 (13)0.0253 (14)0.0254 (13)0.0003 (11)0.0016 (11)0.0013 (11)
C210.0388 (19)0.110 (3)0.0275 (16)0.026 (2)0.0169 (15)0.0232 (18)
C220.0440 (18)0.0312 (16)0.0445 (17)0.0119 (14)0.0048 (15)0.0037 (13)
O5A0.056 (4)0.016 (2)0.030 (3)0.007 (2)0.017 (3)0.0041 (17)
C23A0.108 (9)0.024 (4)0.114 (10)0.011 (5)0.075 (8)0.012 (5)
O5B0.064 (7)0.024 (4)0.056 (6)0.014 (4)0.034 (6)0.011 (3)
C23B0.109 (12)0.044 (6)0.039 (6)0.029 (7)0.002 (7)0.010 (5)
O5C0.125 (12)0.067 (8)0.053 (7)0.011 (8)0.017 (8)0.022 (6)
C23C0.090 (15)0.050 (10)0.137 (18)0.013 (10)0.052 (14)0.043 (11)
Geometric parameters (Å, º) top
O1—C91.367 (3)C14—H14A0.9700
O1—H10.8200C14—H14B0.9700
O2—C101.368 (3)C15—C161.387 (3)
O2—C211.432 (3)C15—C201.391 (3)
O3—C161.363 (3)C16—C171.400 (4)
O3—H30.8200C17—C181.383 (4)
O4—C171.372 (3)C18—C191.380 (4)
O4—C221.416 (3)C18—H18A0.9300
N1—C71.316 (3)C19—C201.379 (4)
N1—C11.396 (3)C19—H19A0.9300
N2—C71.371 (3)C20—H20A0.9300
N2—C61.391 (3)C21—H21A0.9600
N2—C141.457 (3)C21—H21B0.9600
C1—C21.395 (3)C21—H21C0.9600
C1—C61.401 (3)C22—H22A0.9600
C2—C31.386 (4)C22—H22B0.9600
C2—H2A0.9300C22—H22C0.9600
C3—C41.394 (4)O5A—C23A1.439 (9)
C3—H3A0.9300O5A—H5A10.8200
C4—C51.383 (4)C23A—H23A0.9600
C4—H4A0.9300C23A—H23B0.9600
C5—C61.392 (3)C23A—H23C0.9600
C5—H5A0.9300O5B—C23B1.547 (16)
C7—C81.483 (3)O5B—H5B0.8200
C8—C91.382 (3)C23B—H23D0.9600
C8—C131.398 (4)C23B—H23E0.9600
C9—C101.400 (3)C23B—H23F0.9600
C10—C111.380 (4)O5C—C23C1.41 (2)
C11—C121.390 (4)O5C—H5C0.8200
C11—H11A0.9300C23C—C23Ci1.57 (4)
C12—C131.386 (4)C23C—H23G0.9600
C12—H12A0.9300C23C—H23H0.9597
C13—H13A0.9300C23C—H23I0.9602
C14—C151.513 (3)
C9—O1—H1109.5C16—C15—C14117.3 (2)
C10—O2—C21116.3 (2)C20—C15—C14123.4 (2)
C16—O3—H3109.5O3—C16—C15118.0 (2)
C17—O4—C22117.7 (2)O3—C16—C17121.8 (2)
C7—N1—C1105.1 (2)C15—C16—C17120.2 (2)
C7—N2—C6106.90 (19)O4—C17—C18125.2 (2)
C7—N2—C14127.1 (2)O4—C17—C16115.0 (2)
C6—N2—C14126.0 (2)C18—C17—C16119.8 (2)
C2—C1—N1130.3 (2)C19—C18—C17119.8 (2)
C2—C1—C6119.7 (2)C19—C18—H18A120.1
N1—C1—C6110.0 (2)C17—C18—H18A120.1
C3—C2—C1117.8 (2)C20—C19—C18120.6 (2)
C3—C2—H2A121.1C20—C19—H19A119.7
C1—C2—H2A121.1C18—C19—H19A119.7
C2—C3—C4121.5 (2)C19—C20—C15120.4 (2)
C2—C3—H3A119.3C19—C20—H20A119.8
C4—C3—H3A119.3C15—C20—H20A119.8
C5—C4—C3121.8 (2)O2—C21—H21A109.5
C5—C4—H4A119.1O2—C21—H21B109.5
C3—C4—H4A119.1H21A—C21—H21B109.5
C4—C5—C6116.3 (2)O2—C21—H21C109.5
C4—C5—H5A121.8H21A—C21—H21C109.5
C6—C5—H5A121.8H21B—C21—H21C109.5
N2—C6—C5132.1 (2)O4—C22—H22A109.5
N2—C6—C1105.0 (2)O4—C22—H22B109.5
C5—C6—C1122.9 (2)H22A—C22—H22B109.5
N1—C7—N2112.9 (2)O4—C22—H22C109.5
N1—C7—C8126.1 (2)H22A—C22—H22C109.5
N2—C7—C8120.9 (2)H22B—C22—H22C109.5
C9—C8—C13119.5 (2)O5A—C23A—H23A109.5
C9—C8—C7121.1 (2)O5A—C23A—H23B109.5
C13—C8—C7119.4 (2)H23A—C23A—H23B109.5
O1—C9—C8119.5 (2)O5A—C23A—H23C109.5
O1—C9—C10120.7 (2)H23A—C23A—H23C109.5
C8—C9—C10119.8 (2)H23B—C23A—H23C109.5
O2—C10—C11125.5 (2)C23B—O5B—H5B109.5
O2—C10—C9113.8 (2)O5B—C23B—H23D109.5
C11—C10—C9120.7 (2)O5B—C23B—H23E109.5
C10—C11—C12119.4 (2)H23D—C23B—H23E109.5
C10—C11—H11A120.3O5B—C23B—H23F109.5
C12—C11—H11A120.3H23D—C23B—H23F109.5
C13—C12—C11120.3 (2)H23E—C23B—H23F109.5
C13—C12—H12A119.8O5B—C23B—H23H151.5
C11—C12—H12A119.8H23D—C23B—H23H89.8
C12—C13—C8120.2 (2)H23E—C23B—H23H82.0
C12—C13—H13A119.9O5C—C23C—C23Ci88 (2)
C8—C13—H13A119.9O5C—C23C—H23G109.3
N2—C14—C15113.7 (2)O5C—C23C—H23H106.9
N2—C14—H14A108.8C23Ci—C23C—H23H151.2
C15—C14—H14A108.8H23G—C23C—H23H109.5
N2—C14—H14B108.8O5C—C23C—H23I112.2
C15—C14—H14B108.8C23Ci—C23C—H23I85.8
H14A—C14—H14B107.7H23G—C23C—H23I109.5
C16—C15—C20119.2 (2)H23H—C23C—H23I109.5
C7—N1—C1—C2179.5 (2)C21—O2—C10—C9172.4 (3)
C7—N1—C1—C60.7 (3)O1—C9—C10—O20.6 (3)
N1—C1—C2—C3178.3 (2)C8—C9—C10—O2180.0 (2)
C6—C1—C2—C31.6 (3)O1—C9—C10—C11179.5 (2)
C1—C2—C3—C40.9 (4)C8—C9—C10—C111.0 (4)
C2—C3—C4—C50.1 (4)O2—C10—C11—C12179.0 (3)
C3—C4—C5—C60.4 (4)C9—C10—C11—C120.2 (4)
C7—N2—C6—C5178.4 (3)C10—C11—C12—C130.7 (4)
C14—N2—C6—C53.9 (4)C11—C12—C13—C80.8 (4)
C7—N2—C6—C11.5 (2)C9—C8—C13—C120.0 (4)
C14—N2—C6—C1176.2 (2)C7—C8—C13—C12177.9 (2)
C4—C5—C6—N2179.8 (2)C7—N2—C14—C15104.5 (3)
C4—C5—C6—C10.3 (4)C6—N2—C14—C1578.2 (3)
C2—C1—C6—N2178.7 (2)N2—C14—C15—C16171.5 (2)
N1—C1—C6—N21.4 (3)N2—C14—C15—C2011.3 (3)
C2—C1—C6—C51.4 (4)C20—C15—C16—O3176.2 (2)
N1—C1—C6—C5178.5 (2)C14—C15—C16—O31.2 (3)
C1—N1—C7—N20.3 (3)C20—C15—C16—C170.4 (3)
C1—N1—C7—C8175.3 (2)C14—C15—C16—C17177.8 (2)
C6—N2—C7—N11.2 (3)C22—O4—C17—C1830.2 (4)
C14—N2—C7—N1176.5 (2)C22—O4—C17—C16149.2 (2)
C6—N2—C7—C8174.7 (2)O3—C16—C17—O43.0 (3)
C14—N2—C7—C87.6 (4)C15—C16—C17—O4179.5 (2)
N1—C7—C8—C9104.0 (3)O3—C16—C17—C18176.5 (2)
N2—C7—C8—C980.6 (3)C15—C16—C17—C180.0 (4)
N1—C7—C8—C1378.1 (3)O4—C17—C18—C19179.2 (2)
N2—C7—C8—C1397.3 (3)C16—C17—C18—C190.3 (4)
C13—C8—C9—O1179.6 (2)C17—C18—C19—C200.1 (4)
C7—C8—C9—O12.5 (4)C18—C19—C20—C150.4 (4)
C13—C8—C9—C100.9 (4)C16—C15—C20—C190.6 (3)
C7—C8—C9—C10177.0 (2)C14—C15—C20—C19177.8 (2)
C21—O2—C10—C116.5 (4)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.822.212.651 (2)114
O3—H3···O40.822.252.700 (3)114
O3—H3···O5Aii0.821.852.626 (5)157
O5A—H5A1···N1iii0.822.072.842 (5)157
O1—H1···O3iv0.822.192.956 (2)155
C14—H14B···O2iv0.972.463.335 (3)150
C23A—H23B···O5Av0.962.573.215 (16)125
Symmetry codes: (ii) x1, y1, z; (iii) x+1, y, z; (iv) x, y, z; (v) x+2, y+1, z.

Experimental details

Crystal data
Chemical formulaC22H20N2O4·1.13CH4O
Mr412.53
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)7.2451 (1), 11.1482 (2), 26.2046 (5)
β (°) 90.010 (1)
V3)2116.54 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.27 × 0.15 × 0.13
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.976, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
18918, 3940, 3099
Rint0.040
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.122, 1.09
No. of reflections3940
No. of parameters317
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.23

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.82002.21002.651 (2)114.00
O3—H3···O40.82002.25002.700 (3)114.00
O3—H3···O5Ai0.82001.85002.626 (5)157.00
O5A—H5A1···N1ii0.82002.07002.842 (5)157.00
O1—H1···O3iii0.82002.19002.956 (2)155.00
C14—H14B···O2iii0.97002.46003.335 (3)150.00
C23A—H23B···O5Aiv0.96002.57003.215 (16)125.00
Symmetry codes: (i) x1, y1, z; (ii) x+1, y, z; (iii) x, y, z; (iv) x+2, y+1, z.
 

Footnotes

Additional correspondence author, e-mail: ohasnah@usm.my.

Acknowledgements

The authors thank the Malaysian government and Universiti Sains Malaysia (USM) for an FRGS grant (No. 304/PKIMIA/638122) to conduct this work. M. H. Al-Douh thanks the Yemen government and Hadhramout University of Science and Technology (HUST) for financial scholarship support. HKF and RK thank the Malaysian government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

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First citationCosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.  CrossRef CAS Web of Science IUCr Journals Google Scholar
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First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 4| April 2009| Pages o925-o926
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