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

Al-Douh, M.H.; Osman, H.; Hamid, S.A.; Kia, R.; Fun, H.-K.

doi:10.1107/S1600536809011192

organic compounds

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ISSN: 2056-9890

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

doi:10.1107/S1600536809011192

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

Mohammed H. Al-Douh,^a Hasnah Osman,^a ‡ Shafida A. Hamid,^b Reza Kia ^c and Hoong-Kun Fun ^c ^*

^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 , 2009 ). For hydrogen-bond motifs, see Bernstein et al. (1995 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₂H₂₀N₂O₄·1.13CH₄O
M_r = 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 ) T_min = 0.976, T_max = 0.988
18918 measured reflections
3940 independent reflections
3099 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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⋯O5A^iv	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); cell refinement: SAINT (Bruker, 2005); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809011192/cv2535sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809011192/cv2535Isup2.hkl

checkCIF report

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···C21^vi of 3.209 (4) Å and C17···C21^vi 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.

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

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

C₂₂H₂₀N₂O₄·1.13CH₄O	F(000) = 873
M_r = 412.53	D_x = 1.295 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4846 reflections
a = 7.2451 (1) Å	θ = 2.9–26.4°
b = 11.1482 (2) Å	µ = 0.09 mm⁻¹
c = 26.2046 (5) Å	T = 100 K
β = 90.010 (1)°	Block, colourless
V = 2116.54 (6) Å³	0.27 × 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 tube	3099 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 25.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
T_min = 0.976, T_max = 0.988	k = −12→13
18918 measured reflections	l = −31→28

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0415P)² + 1.5448P] where P = (F_o² + 2F_c²)/3
3940 reflections	(Δ/σ)_max < 0.001
317 parameters	Δρ_max = 0.28 e Å⁻³
1 restraint	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₂H₂₀N₂O₄·1.13CH₄O	V = 2116.54 (6) Å³
M_r = 412.53	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.2451 (1) Å	µ = 0.09 mm⁻¹
b = 11.1482 (2) Å	T = 100 K
c = 26.2046 (5) Å	0.27 × 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)
T_min = 0.976, T_max = 0.988	R_int = 0.040
18918 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	1 restraint
wR(F²) = 0.122	H-atom parameters constrained
S = 1.09	Δρ_max = 0.28 e Å⁻³
3940 reflections	Δρ_min = −0.23 e Å⁻³
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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.0363 (2)	0.18739 (17)	0.00815 (6)	0.0272 (4)
H1	0.0385	0.1891	−0.0231	0.041*
O2	0.3146 (2)	0.15819 (18)	−0.05634 (6)	0.0346 (5)
O3	0.0521 (3)	−0.24674 (15)	0.09905 (6)	0.0282 (4)
H3	0.0664	−0.3196	0.0971	0.042*
O4	0.2424 (3)	−0.39894 (16)	0.15953 (8)	0.0437 (6)
N1	0.0259 (3)	0.31698 (18)	0.13518 (7)	0.0220 (5)
N2	−0.0044 (3)	0.11719 (17)	0.13178 (7)	0.0196 (5)
C1	−0.1122 (3)	0.2812 (2)	0.16904 (9)	0.0199 (5)
C2	−0.2243 (3)	0.3492 (2)	0.20124 (9)	0.0237 (6)
H2A	−0.2161	0.4324	0.2019	0.028*
C3	−0.3483 (3)	0.2886 (2)	0.23220 (9)	0.0253 (6)
H3A	−0.4232	0.3321	0.2543	0.030*
C4	−0.3634 (4)	0.1640 (2)	0.23092 (9)	0.0255 (6)
H4A	−0.4479	0.1264	0.2523	0.031*
C5	−0.2560 (3)	0.0947 (2)	0.19875 (9)	0.0229 (6)
H5A	−0.2666	0.0116	0.1977	0.027*
C6	−0.1313 (3)	0.1562 (2)	0.16799 (8)	0.0195 (5)
C7	0.0860 (3)	0.2171 (2)	0.11421 (9)	0.0198 (5)
C8	0.2427 (3)	0.2062 (2)	0.07811 (9)	0.0196 (5)
C9	0.2130 (3)	0.1894 (2)	0.02649 (9)	0.0202 (5)
C10	0.3634 (4)	0.1738 (2)	−0.00633 (9)	0.0233 (6)
C11	0.5417 (4)	0.1767 (2)	0.01214 (10)	0.0289 (6)
H11A	0.6411	0.1665	−0.0099	0.035*
C12	0.5715 (4)	0.1951 (3)	0.06398 (10)	0.0324 (7)
H12A	0.6913	0.1981	0.0766	0.039*
C13	0.4233 (3)	0.2090 (2)	0.09689 (10)	0.0281 (6)
H13A	0.4441	0.2203	0.1316	0.034*
C14	0.0209 (3)	−0.0061 (2)	0.11471 (9)	0.0203 (5)
H14A	0.0840	−0.0054	0.0821	0.024*
H14B	−0.0994	−0.0423	0.1095	0.024*
C15	0.1298 (3)	−0.0828 (2)	0.15162 (9)	0.0193 (5)
C16	0.1386 (3)	−0.2048 (2)	0.14165 (9)	0.0210 (5)
C17	0.2424 (4)	−0.2802 (2)	0.17332 (10)	0.0256 (6)
C18	0.3361 (4)	−0.2327 (2)	0.21462 (10)	0.0267 (6)
H18A	0.4048	−0.2825	0.2358	0.032*
C19	0.3274 (3)	−0.1111 (2)	0.22427 (10)	0.0263 (6)
H19A	0.3906	−0.0793	0.2520	0.032*
C20	0.2259 (3)	−0.0364 (2)	0.19313 (9)	0.0241 (6)
H20A	0.2217	0.0454	0.1999	0.029*
C21	0.4624 (5)	0.1568 (4)	−0.09260 (11)	0.0588 (11)
H21A	0.4126	0.1590	−0.1265	0.088*
H21B	0.5337	0.0849	−0.0883	0.088*
H21C	0.5400	0.2255	−0.0873	0.088*
C22	0.4019 (4)	−0.4674 (3)	0.17089 (12)	0.0399 (7)
H22A	0.5094	−0.4261	0.1587	0.060*
H22B	0.3931	−0.5443	0.1546	0.060*
H22C	0.4112	−0.4783	0.2071	0.060*
O5A	1.0245 (11)	0.5263 (4)	0.0733 (2)	0.034 (2)	0.506 (13)
H5A1	1.0285	0.4805	0.0978	0.051*	0.506 (13)
C23A	0.8593 (19)	0.5039 (7)	0.0444 (6)	0.082 (5)	0.506 (13)
H23A	0.8527	0.4203	0.0358	0.123*	0.506 (13)
H23B	0.8616	0.5507	0.0136	0.123*	0.506 (13)
H23C	0.7534	0.5257	0.0643	0.123*	0.506 (13)
O5B	0.9164 (17)	0.5416 (6)	0.0975 (4)	0.048 (4)	0.373 (13)
H5B	0.9997	0.4977	0.0874	0.072*	0.373 (13)
C23B	0.739 (3)	0.5162 (11)	0.0664 (4)	0.064 (4)	0.373 (13)
H23D	0.7633	0.4547	0.0417	0.096*	0.373 (13)
H23E	0.7007	0.5881	0.0493	0.096*	0.373 (13)
H23F	0.6429	0.4900	0.0891	0.096*	0.373 (13)
O5C	0.718 (2)	0.4931 (11)	0.0088 (4)	0.082 (4)	0.249 (5)
H5C	0.7138	0.4829	−0.0222	0.123*	0.249 (5)
C23C	0.537 (3)	0.5098 (15)	0.0278 (8)	0.092 (7)	0.249 (5)
H23G	0.4542	0.4569	0.0102	0.139*	0.249 (5)
H23H	0.5401	0.4894	0.0633	0.139*	0.249 (5)
H23I	0.4957	0.5911	0.0239	0.139*	0.249 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0169 (9)	0.0456 (11)	0.0192 (9)	−0.0011 (8)	0.0000 (7)	−0.0004 (8)
O2	0.0215 (10)	0.0621 (13)	0.0202 (9)	−0.0080 (9)	0.0070 (8)	−0.0083 (9)
O3	0.0329 (10)	0.0216 (9)	0.0302 (10)	0.0024 (8)	−0.0068 (8)	−0.0033 (7)
O4	0.0460 (13)	0.0217 (10)	0.0633 (14)	0.0073 (9)	−0.0233 (11)	−0.0015 (9)
N1	0.0227 (11)	0.0222 (11)	0.0212 (10)	−0.0008 (9)	0.0010 (9)	0.0005 (9)
N2	0.0197 (11)	0.0203 (11)	0.0188 (10)	0.0011 (9)	0.0016 (9)	0.0001 (8)
C1	0.0194 (12)	0.0224 (13)	0.0179 (11)	0.0008 (10)	−0.0033 (10)	−0.0011 (10)
C2	0.0222 (13)	0.0258 (14)	0.0231 (13)	0.0033 (11)	−0.0044 (11)	−0.0039 (11)
C3	0.0197 (13)	0.0343 (15)	0.0220 (12)	0.0064 (12)	0.0010 (11)	−0.0048 (11)
C4	0.0207 (13)	0.0348 (15)	0.0210 (12)	−0.0006 (12)	0.0027 (11)	0.0019 (11)
C5	0.0234 (13)	0.0231 (13)	0.0220 (12)	0.0017 (11)	0.0002 (11)	0.0036 (10)
C6	0.0175 (12)	0.0248 (13)	0.0163 (11)	0.0047 (11)	−0.0010 (10)	−0.0020 (10)
C7	0.0201 (13)	0.0212 (13)	0.0182 (11)	0.0015 (11)	−0.0030 (10)	0.0011 (10)
C8	0.0196 (12)	0.0187 (12)	0.0204 (12)	0.0006 (10)	0.0020 (10)	0.0009 (10)
C9	0.0157 (12)	0.0203 (13)	0.0246 (12)	0.0003 (10)	0.0002 (10)	0.0002 (10)
C10	0.0233 (13)	0.0258 (14)	0.0208 (12)	−0.0035 (11)	0.0013 (11)	−0.0023 (10)
C11	0.0192 (13)	0.0366 (16)	0.0310 (14)	0.0028 (12)	0.0064 (11)	−0.0009 (12)
C12	0.0162 (13)	0.0496 (18)	0.0314 (15)	0.0010 (13)	−0.0038 (12)	0.0039 (13)
C13	0.0231 (14)	0.0394 (16)	0.0219 (13)	0.0032 (12)	−0.0023 (11)	0.0013 (12)
C14	0.0204 (12)	0.0216 (13)	0.0188 (12)	0.0004 (11)	0.0014 (10)	−0.0003 (10)
C15	0.0154 (12)	0.0232 (13)	0.0194 (12)	−0.0001 (10)	0.0051 (10)	0.0002 (10)
C16	0.0170 (12)	0.0248 (13)	0.0212 (12)	−0.0005 (11)	0.0032 (10)	0.0004 (10)
C17	0.0237 (13)	0.0208 (13)	0.0324 (14)	−0.0007 (11)	−0.0003 (12)	0.0039 (11)
C18	0.0228 (14)	0.0280 (15)	0.0292 (14)	0.0028 (12)	−0.0023 (12)	0.0102 (11)
C19	0.0222 (14)	0.0315 (15)	0.0253 (13)	−0.0009 (12)	−0.0042 (11)	0.0013 (11)
C20	0.0215 (13)	0.0253 (14)	0.0254 (13)	−0.0003 (11)	0.0016 (11)	−0.0013 (11)
C21	0.0388 (19)	0.110 (3)	0.0275 (16)	−0.026 (2)	0.0169 (15)	−0.0232 (18)
C22	0.0440 (18)	0.0312 (16)	0.0445 (17)	0.0119 (14)	0.0048 (15)	0.0037 (13)
O5A	0.056 (4)	0.016 (2)	0.030 (3)	−0.007 (2)	−0.017 (3)	0.0041 (17)
C23A	0.108 (9)	0.024 (4)	0.114 (10)	−0.011 (5)	−0.075 (8)	0.012 (5)
O5B	0.064 (7)	0.024 (4)	0.056 (6)	−0.014 (4)	−0.034 (6)	0.011 (3)
C23B	0.109 (12)	0.044 (6)	0.039 (6)	−0.029 (7)	0.002 (7)	−0.010 (5)
O5C	0.125 (12)	0.067 (8)	0.053 (7)	−0.011 (8)	−0.017 (8)	0.022 (6)
C23C	0.090 (15)	0.050 (10)	0.137 (18)	−0.013 (10)	−0.052 (14)	0.043 (11)

Geometric parameters (Å, º) top

O1—C9	1.367 (3)	C14—H14A	0.9700
O1—H1	0.8200	C14—H14B	0.9700
O2—C10	1.368 (3)	C15—C16	1.387 (3)
O2—C21	1.432 (3)	C15—C20	1.391 (3)
O3—C16	1.363 (3)	C16—C17	1.400 (4)
O3—H3	0.8200	C17—C18	1.383 (4)
O4—C17	1.372 (3)	C18—C19	1.380 (4)
O4—C22	1.416 (3)	C18—H18A	0.9300
N1—C7	1.316 (3)	C19—C20	1.379 (4)
N1—C1	1.396 (3)	C19—H19A	0.9300
N2—C7	1.371 (3)	C20—H20A	0.9300
N2—C6	1.391 (3)	C21—H21A	0.9600
N2—C14	1.457 (3)	C21—H21B	0.9600
C1—C2	1.395 (3)	C21—H21C	0.9600
C1—C6	1.401 (3)	C22—H22A	0.9600
C2—C3	1.386 (4)	C22—H22B	0.9600
C2—H2A	0.9300	C22—H22C	0.9600
C3—C4	1.394 (4)	O5A—C23A	1.439 (9)
C3—H3A	0.9300	O5A—H5A1	0.8200
C4—C5	1.383 (4)	C23A—H23A	0.9600
C4—H4A	0.9300	C23A—H23B	0.9600
C5—C6	1.392 (3)	C23A—H23C	0.9600
C5—H5A	0.9300	O5B—C23B	1.547 (16)
C7—C8	1.483 (3)	O5B—H5B	0.8200
C8—C9	1.382 (3)	C23B—H23D	0.9600
C8—C13	1.398 (4)	C23B—H23E	0.9600
C9—C10	1.400 (3)	C23B—H23F	0.9600
C10—C11	1.380 (4)	O5C—C23C	1.41 (2)
C11—C12	1.390 (4)	O5C—H5C	0.8200
C11—H11A	0.9300	C23C—C23Cⁱ	1.57 (4)
C12—C13	1.386 (4)	C23C—H23G	0.9600
C12—H12A	0.9300	C23C—H23H	0.9597
C13—H13A	0.9300	C23C—H23I	0.9602
C14—C15	1.513 (3)

C9—O1—H1	109.5	C16—C15—C14	117.3 (2)
C10—O2—C21	116.3 (2)	C20—C15—C14	123.4 (2)
C16—O3—H3	109.5	O3—C16—C15	118.0 (2)
C17—O4—C22	117.7 (2)	O3—C16—C17	121.8 (2)
C7—N1—C1	105.1 (2)	C15—C16—C17	120.2 (2)
C7—N2—C6	106.90 (19)	O4—C17—C18	125.2 (2)
C7—N2—C14	127.1 (2)	O4—C17—C16	115.0 (2)
C6—N2—C14	126.0 (2)	C18—C17—C16	119.8 (2)
C2—C1—N1	130.3 (2)	C19—C18—C17	119.8 (2)
C2—C1—C6	119.7 (2)	C19—C18—H18A	120.1
N1—C1—C6	110.0 (2)	C17—C18—H18A	120.1
C3—C2—C1	117.8 (2)	C20—C19—C18	120.6 (2)
C3—C2—H2A	121.1	C20—C19—H19A	119.7
C1—C2—H2A	121.1	C18—C19—H19A	119.7
C2—C3—C4	121.5 (2)	C19—C20—C15	120.4 (2)
C2—C3—H3A	119.3	C19—C20—H20A	119.8
C4—C3—H3A	119.3	C15—C20—H20A	119.8
C5—C4—C3	121.8 (2)	O2—C21—H21A	109.5
C5—C4—H4A	119.1	O2—C21—H21B	109.5
C3—C4—H4A	119.1	H21A—C21—H21B	109.5
C4—C5—C6	116.3 (2)	O2—C21—H21C	109.5
C4—C5—H5A	121.8	H21A—C21—H21C	109.5
C6—C5—H5A	121.8	H21B—C21—H21C	109.5
N2—C6—C5	132.1 (2)	O4—C22—H22A	109.5
N2—C6—C1	105.0 (2)	O4—C22—H22B	109.5
C5—C6—C1	122.9 (2)	H22A—C22—H22B	109.5
N1—C7—N2	112.9 (2)	O4—C22—H22C	109.5
N1—C7—C8	126.1 (2)	H22A—C22—H22C	109.5
N2—C7—C8	120.9 (2)	H22B—C22—H22C	109.5
C9—C8—C13	119.5 (2)	O5A—C23A—H23A	109.5
C9—C8—C7	121.1 (2)	O5A—C23A—H23B	109.5
C13—C8—C7	119.4 (2)	H23A—C23A—H23B	109.5
O1—C9—C8	119.5 (2)	O5A—C23A—H23C	109.5
O1—C9—C10	120.7 (2)	H23A—C23A—H23C	109.5
C8—C9—C10	119.8 (2)	H23B—C23A—H23C	109.5
O2—C10—C11	125.5 (2)	C23B—O5B—H5B	109.5
O2—C10—C9	113.8 (2)	O5B—C23B—H23D	109.5
C11—C10—C9	120.7 (2)	O5B—C23B—H23E	109.5
C10—C11—C12	119.4 (2)	H23D—C23B—H23E	109.5
C10—C11—H11A	120.3	O5B—C23B—H23F	109.5
C12—C11—H11A	120.3	H23D—C23B—H23F	109.5
C13—C12—C11	120.3 (2)	H23E—C23B—H23F	109.5
C13—C12—H12A	119.8	O5B—C23B—H23H	151.5
C11—C12—H12A	119.8	H23D—C23B—H23H	89.8
C12—C13—C8	120.2 (2)	H23E—C23B—H23H	82.0
C12—C13—H13A	119.9	O5C—C23C—C23Cⁱ	88 (2)
C8—C13—H13A	119.9	O5C—C23C—H23G	109.3
N2—C14—C15	113.7 (2)	O5C—C23C—H23H	106.9
N2—C14—H14A	108.8	C23Cⁱ—C23C—H23H	151.2
C15—C14—H14A	108.8	H23G—C23C—H23H	109.5
N2—C14—H14B	108.8	O5C—C23C—H23I	112.2
C15—C14—H14B	108.8	C23Cⁱ—C23C—H23I	85.8
H14A—C14—H14B	107.7	H23G—C23C—H23I	109.5
C16—C15—C20	119.2 (2)	H23H—C23C—H23I	109.5

C7—N1—C1—C2	−179.5 (2)	C21—O2—C10—C9	172.4 (3)
C7—N1—C1—C6	0.7 (3)	O1—C9—C10—O2	0.6 (3)
N1—C1—C2—C3	−178.3 (2)	C8—C9—C10—O2	−180.0 (2)
C6—C1—C2—C3	1.6 (3)	O1—C9—C10—C11	179.5 (2)
C1—C2—C3—C4	−0.9 (4)	C8—C9—C10—C11	−1.0 (4)
C2—C3—C4—C5	−0.1 (4)	O2—C10—C11—C12	179.0 (3)
C3—C4—C5—C6	0.4 (4)	C9—C10—C11—C12	0.2 (4)
C7—N2—C6—C5	−178.4 (3)	C10—C11—C12—C13	0.7 (4)
C14—N2—C6—C5	3.9 (4)	C11—C12—C13—C8	−0.8 (4)
C7—N2—C6—C1	1.5 (2)	C9—C8—C13—C12	0.0 (4)
C14—N2—C6—C1	−176.2 (2)	C7—C8—C13—C12	177.9 (2)
C4—C5—C6—N2	−179.8 (2)	C7—N2—C14—C15	104.5 (3)
C4—C5—C6—C1	0.3 (4)	C6—N2—C14—C15	−78.2 (3)
C2—C1—C6—N2	178.7 (2)	N2—C14—C15—C16	171.5 (2)
N1—C1—C6—N2	−1.4 (3)	N2—C14—C15—C20	−11.3 (3)
C2—C1—C6—C5	−1.4 (4)	C20—C15—C16—O3	−176.2 (2)
N1—C1—C6—C5	178.5 (2)	C14—C15—C16—O3	1.2 (3)
C1—N1—C7—N2	0.3 (3)	C20—C15—C16—C17	0.4 (3)
C1—N1—C7—C8	−175.3 (2)	C14—C15—C16—C17	177.8 (2)
C6—N2—C7—N1	−1.2 (3)	C22—O4—C17—C18	−30.2 (4)
C14—N2—C7—N1	176.5 (2)	C22—O4—C17—C16	149.2 (2)
C6—N2—C7—C8	174.7 (2)	O3—C16—C17—O4	−3.0 (3)
C14—N2—C7—C8	−7.6 (4)	C15—C16—C17—O4	−179.5 (2)
N1—C7—C8—C9	−104.0 (3)	O3—C16—C17—C18	176.5 (2)
N2—C7—C8—C9	80.6 (3)	C15—C16—C17—C18	0.0 (4)
N1—C7—C8—C13	78.1 (3)	O4—C17—C18—C19	179.2 (2)
N2—C7—C8—C13	−97.3 (3)	C16—C17—C18—C19	−0.3 (4)
C13—C8—C9—O1	−179.6 (2)	C17—C18—C19—C20	0.1 (4)
C7—C8—C9—O1	2.5 (4)	C18—C19—C20—C15	0.4 (4)
C13—C8—C9—C10	0.9 (4)	C16—C15—C20—C19	−0.6 (3)
C7—C8—C9—C10	−177.0 (2)	C14—C15—C20—C19	−177.8 (2)
C21—O2—C10—C11	−6.5 (4)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	2.21	2.651 (2)	114
O3—H3···O4	0.82	2.25	2.700 (3)	114
O3—H3···O5Aⁱⁱ	0.82	1.85	2.626 (5)	157
O5A—H5A1···N1ⁱⁱⁱ	0.82	2.07	2.842 (5)	157
O1—H1···O3^iv	0.82	2.19	2.956 (2)	155
C14—H14B···O2^iv	0.97	2.46	3.335 (3)	150
C23A—H23B···O5A^v	0.96	2.57	3.215 (16)	125

Symmetry codes: (ii) x−1, y−1, z; (iii) x+1, y, z; (iv) −x, −y, −z; (v) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₀N₂O₄·1.13CH₄O
M_r	412.53
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	7.2451 (1), 11.1482 (2), 26.2046 (5)
β (°)	90.010 (1)
V (Å³)	2116.54 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.27 × 0.15 × 0.13

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.976, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	18918, 3940, 3099
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.122, 1.09
No. of reflections	3940
No. of parameters	317
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.8200	2.2100	2.651 (2)	114.00
O3—H3···O4	0.8200	2.2500	2.700 (3)	114.00
O3—H3···O5Aⁱ	0.8200	1.8500	2.626 (5)	157.00
O5A—H5A1···N1ⁱⁱ	0.8200	2.0700	2.842 (5)	157.00
O1—H1···O3ⁱⁱⁱ	0.8200	2.1900	2.956 (2)	155.00
C14—H14B···O2ⁱⁱⁱ	0.9700	2.4600	3.335 (3)	150.00
C23A—H23B···O5A^iv	0.9600	2.5700	3.215 (16)	125.00

Symmetry codes: (i) x−1, y−1, 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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