Ethyl 1-tert-butyl-2-(4-hydr­oxy-3-methoxy­phen­yl)-1H-benzimidazole-5-carboxyl­ate

Arumugam, N.; Abdul Rahim, A.S.; Osman, H.; Rosli, M.M.; Fun, H.-K.

doi:10.1107/S1600536810011918

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 5| May 2010| Pages o1051-o1052

https://doi.org/10.1107/S1600536810011918

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Ethyl 1-tert-butyl-2-(4-hydroxy-3-methoxyphenyl)-1H-benzimidazole-5-carboxylate

Natarajan Arumugam,^a Aisyah Saad Abdul Rahim,^a ‡ Hasnah Osman,^b Mohd Mustaqim Rosli ^c and Hoong-Kun Fun ^c ^*§

^aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 25 March 2010; accepted 30 March 2010; online 10 April 2010)

In the title compound, C₂₁H₂₄N₂O₄, the benzimidazole ring system is almost planar, with a maximum deviation of 0.047 (1) Å and makes a dihedral angle of 88.44 (5)° with the attached benzene ring. In the crystal, molecules form infinite chains along the b axis by way of intermolecular O—H⋯N and C—H⋯O interactions. Weak C—H⋯π also contribute to the stabilization of the crystal structure.

Related literature

For the biological properties of benzimidazole-based heterocyclic compounds, see: Townsend et al. (1970 ); Blythin et al. (1986 ); Lemura et al. (1986 ); Zhang et al. (2008 ); Bonfanti et al. (2008 ); Ozden et al. (2008 ). For related structures, see Arumugam, Abd Hamid et al. (2010 ); Arumugam, Abdul Rahim, Abd Hamid et al. (2010 ); Arumugam, Abdul Rahim, Osman et al. (2010 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₁H₂₄N₂O₄
M_r = 368.42
Monoclinic, P 2₁ /c
a = 9.2610 (6) Å
b = 13.6096 (9) Å
c = 16.3200 (9) Å
β = 113.560 (3)°
V = 1885.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.38 × 0.23 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.967, T_max = 0.986
21041 measured reflections
5484 independent reflections
4104 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.134
S = 1.07
5484 reflections
253 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N1ⁱ	0.85 (2)	1.97 (2)	2.7475 (17)	151.7 (19)
C2—H2A⋯O2ⁱⁱ	0.93	2.58	3.3648 (17)	142
C13—H13A⋯O3ⁱⁱⁱ	0.93	2.56	3.4223 (17)	154
C18—H18B⋯O4ⁱⁱⁱ	0.96	2.60	3.514 (2)	160
C18—H18C⋯O1^iv	0.96	2.54	3.4753 (17)	163
C18—H18A⋯Cg1^v	0.96	2.89	3.5798 (16)	129
C20—H20B⋯Cg1	0.96	2.81	3.4764 (17)	127
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x, -y+1, -z+1; (iv) -x, -y, -z+1; (v) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

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: https://doi.org/10.1107/S1600536810011918/wn2380sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810011918/wn2380Isup2.hkl

checkCIF report

Comment top

Benzimidazole-based heterocycles are known to exhibit antihistamine (Lemura et al., 1986), immunosuppressive (Zhang et al., 2008), anti-inflammatory (Blythin et al., 1986), antiviral (Bonfanti et al., 2008) and antibacterial (Ozden et al., 2008) activities. In particular, substituted benzimidazole derivatives act as potential anticancer agents (Townsend et al., 1970). In view of their importance, the crystal structure determination of the title compound was carried out and the results are presented here.

All molecular geometric parameters in the title compound are within normal ranges and are comparable with those in related crystal structures (Arumugam, Abd Hamid et al. (2010); Arumugam, Abdul Rahim, Abd Hamid et al. (2010); Arumugam, Abdul Rahim, Osman et al. (2010)). The benzimidazole ring system (N1/N2/C1-C7) is planar with a maximum deviation of 0.047 (1) Å for atom C1. The dihedral angle between the benzimidazole ring system (N1/N2/C1-C7) and the attached benzene ring (C8-C13) is 88.44 (5)°.

In the crystal structure, molecules are connected by intermolecluar O1—H1O1···N1ⁱ, C2—H2A···O2ⁱⁱ, C13—H13A···O3ⁱⁱⁱ, C18—H18B···O4ⁱⁱⁱ and C18—H18C···O1^iv interactions (Table 1). These interactions link the molecules to form infinite one-dimensional chains along the b-axis (Fig. 2). The crystal structure is further stabilized by C—H···π interactions (Table 1), involving the C8-C13 (centroid Cg1) rings.

Related literature top

For the biological properties of benzimidazole-based heterocyclic compounds, see: Townsend et al. (1970); Blythin et al. (1986); Lemura et al. (1986); Zhang et al. (2008); Bonfanti et al. (2008); Ozden et al. (2008). For related structures, see Arumugam, Abd Hamid et al. (2010); Arumugam, Abdul Rahim, Abd Hamid et al. (2010); Arumugam, Abdul Rahim, Osman et al. (2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was synthesised according to the previous procedure described by us (Arumugam, Abd Hamid et al. (2010); Arumugam, Abdul Rahim, Abd Hamid et al. (2010); Arumugam, Abdul Rahim, Osman et al. (2010)). The product was recrystallised from EtOAc to afford the title compound as colourless crystals.

Structure description top

For the biological properties of benzimidazole-based heterocyclic compounds, see: Townsend et al. (1970); Blythin et al. (1986); Lemura et al. (1986); Zhang et al. (2008); Bonfanti et al. (2008); Ozden et al. (2008). For related structures, see Arumugam, Abd Hamid et al. (2010); Arumugam, Abdul Rahim, Abd Hamid et al. (2010); Arumugam, Abdul Rahim, Osman et al. (2010). For the stability of the temperature controller used in the data collection, see: 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

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. The crystal structure of the title compound, showing infinite chains along the b-axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in these interactions have been omitted for clarity.

Ethyl 1-tert-butyl-2-(4-hydroxy-3-methoxyphenyl)- 1H-benzimidazole-5-carboxylate top

Crystal data top

C₂₁H₂₄N₂O₄	F(000) = 784
M_r = 368.42	D_x = 1.298 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4617 reflections
a = 9.2610 (6) Å	θ = 2.4–30.0°
b = 13.6096 (9) Å	µ = 0.09 mm⁻¹
c = 16.3200 (9) Å	T = 100 K
β = 113.560 (3)°	Block, colourless
V = 1885.5 (2) Å³	0.38 × 0.23 × 0.15 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5484 independent reflections
Radiation source: fine-focus sealed tube	4104 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
φ and ω scans	θ_max = 30.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
T_min = 0.967, T_max = 0.986	k = −16→19
21041 measured reflections	l = −22→22

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0645P)² + 0.3983P] where P = (F_o² + 2F_c²)/3
5484 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₂₁H₂₄N₂O₄	V = 1885.5 (2) Å³
M_r = 368.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.2610 (6) Å	µ = 0.09 mm⁻¹
b = 13.6096 (9) Å	T = 100 K
c = 16.3200 (9) Å	0.38 × 0.23 × 0.15 mm
β = 113.560 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5484 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4104 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.986	R_int = 0.039
21041 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.36 e Å⁻³
5484 reflections	Δρ_min = −0.38 e Å⁻³
253 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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.07059 (12)	−0.06665 (7)	0.77515 (6)	0.0237 (2)
O2	−0.19758 (11)	0.02786 (7)	0.67345 (6)	0.0254 (2)
O3	0.35717 (13)	0.74808 (8)	0.53807 (7)	0.0364 (3)
O4	0.36828 (12)	0.71957 (7)	0.67609 (7)	0.0287 (2)
N1	0.14388 (13)	0.37334 (8)	0.65777 (7)	0.0217 (2)
N2	0.14885 (12)	0.29733 (8)	0.53582 (7)	0.0188 (2)
C1	0.18878 (14)	0.44031 (9)	0.60878 (8)	0.0197 (2)
C2	0.23604 (15)	0.53759 (9)	0.63023 (9)	0.0216 (3)
H2A	0.2337	0.5669	0.6812	0.026*
C3	0.28664 (15)	0.58934 (10)	0.57327 (9)	0.0226 (3)
C4	0.28918 (17)	0.54393 (11)	0.49670 (9)	0.0280 (3)
H4A	0.3209	0.5803	0.4586	0.034*
C5	0.24598 (17)	0.44675 (11)	0.47600 (9)	0.0266 (3)
H5A	0.2513	0.4171	0.4259	0.032*
C6	0.19403 (14)	0.39470 (9)	0.53306 (8)	0.0189 (2)
C7	0.12336 (15)	0.28957 (9)	0.61386 (8)	0.0191 (2)
C8	0.10037 (15)	0.19642 (9)	0.65461 (8)	0.0200 (2)
C9	0.23493 (16)	0.14552 (10)	0.70872 (9)	0.0230 (3)
H9A	0.3338	0.1700	0.7176	0.028*
C10	0.22263 (15)	0.05846 (10)	0.74952 (8)	0.0225 (3)
H10A	0.3135	0.0253	0.7859	0.027*
C11	0.07666 (15)	0.02047 (9)	0.73664 (8)	0.0200 (2)
C12	−0.05955 (14)	0.07243 (9)	0.68283 (8)	0.0194 (2)
C13	−0.04751 (15)	0.16086 (9)	0.64290 (8)	0.0208 (2)
H13A	−0.1378	0.1959	0.6086	0.025*
C14	0.34014 (15)	0.69310 (10)	0.59183 (10)	0.0259 (3)
C15	0.42106 (18)	0.82010 (11)	0.70149 (11)	0.0345 (3)
H15A	0.3440	0.8664	0.6631	0.041*
H15B	0.5206	0.8316	0.6966	0.041*
C16	0.43956 (19)	0.83178 (12)	0.79658 (12)	0.0391 (4)
H16A	0.4813	0.8958	0.8179	0.059*
H16B	0.5104	0.7825	0.8330	0.059*
H16C	0.3388	0.8245	0.7998	0.059*
C17	0.13687 (15)	0.22114 (10)	0.46624 (8)	0.0216 (3)
C18	0.03674 (17)	0.26257 (11)	0.37384 (9)	0.0288 (3)
H18A	0.0878	0.3193	0.3627	0.043*
H18B	−0.0649	0.2809	0.3715	0.043*
H18C	0.0244	0.2135	0.3292	0.043*
C19	0.30259 (19)	0.19690 (15)	0.47440 (12)	0.0442 (4)
H19A	0.3547	0.2562	0.4694	0.066*
H19B	0.2968	0.1524	0.4276	0.066*
H19C	0.3608	0.1669	0.5314	0.066*
C20	0.0556 (2)	0.12740 (11)	0.47674 (10)	0.0371 (4)
H20A	−0.0449	0.1436	0.4774	0.056*
H20B	0.1198	0.0956	0.5318	0.056*
H20C	0.0406	0.0840	0.4276	0.056*
C21	−0.34028 (17)	0.07449 (12)	0.61686 (11)	0.0351 (3)
H21A	−0.4283	0.0351	0.6138	0.053*
H21B	−0.3418	0.0818	0.5580	0.053*
H21C	−0.3470	0.1381	0.6406	0.053*
H1O1	−0.017 (2)	−0.0742 (15)	0.7803 (13)	0.043 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0303 (5)	0.0185 (5)	0.0257 (5)	0.0017 (4)	0.0147 (4)	0.0052 (4)
O2	0.0234 (4)	0.0252 (5)	0.0272 (5)	−0.0011 (4)	0.0097 (4)	0.0039 (4)
O3	0.0399 (6)	0.0290 (6)	0.0354 (6)	−0.0100 (4)	0.0098 (5)	0.0102 (4)
O4	0.0335 (5)	0.0167 (5)	0.0321 (5)	−0.0054 (4)	0.0090 (4)	−0.0001 (4)
N1	0.0333 (6)	0.0147 (5)	0.0223 (5)	−0.0016 (4)	0.0165 (4)	−0.0007 (4)
N2	0.0254 (5)	0.0159 (5)	0.0167 (5)	0.0003 (4)	0.0102 (4)	−0.0001 (4)
C1	0.0244 (6)	0.0160 (6)	0.0209 (6)	0.0017 (4)	0.0113 (5)	0.0014 (4)
C2	0.0278 (6)	0.0160 (6)	0.0233 (6)	0.0006 (5)	0.0127 (5)	0.0007 (5)
C3	0.0225 (6)	0.0192 (6)	0.0248 (6)	−0.0014 (5)	0.0082 (5)	0.0035 (5)
C4	0.0327 (7)	0.0291 (7)	0.0236 (6)	−0.0071 (6)	0.0129 (5)	0.0047 (5)
C5	0.0345 (7)	0.0286 (7)	0.0198 (6)	−0.0048 (6)	0.0141 (5)	0.0004 (5)
C6	0.0211 (5)	0.0180 (6)	0.0181 (5)	0.0006 (4)	0.0084 (4)	0.0019 (4)
C7	0.0257 (6)	0.0158 (6)	0.0180 (5)	0.0010 (5)	0.0109 (5)	−0.0001 (4)
C8	0.0308 (6)	0.0139 (5)	0.0175 (5)	−0.0014 (5)	0.0121 (5)	−0.0018 (4)
C9	0.0269 (6)	0.0194 (6)	0.0239 (6)	−0.0012 (5)	0.0115 (5)	0.0002 (5)
C10	0.0254 (6)	0.0199 (6)	0.0221 (6)	0.0022 (5)	0.0096 (5)	0.0019 (5)
C11	0.0292 (6)	0.0156 (6)	0.0170 (5)	0.0004 (5)	0.0112 (5)	−0.0009 (4)
C12	0.0246 (6)	0.0179 (6)	0.0171 (5)	−0.0007 (5)	0.0096 (4)	−0.0017 (4)
C13	0.0278 (6)	0.0174 (6)	0.0174 (5)	0.0010 (5)	0.0093 (5)	−0.0001 (4)
C14	0.0224 (6)	0.0209 (6)	0.0305 (7)	−0.0021 (5)	0.0066 (5)	0.0057 (5)
C15	0.0337 (7)	0.0170 (6)	0.0434 (9)	−0.0045 (5)	0.0055 (6)	0.0015 (6)
C16	0.0315 (7)	0.0257 (8)	0.0512 (10)	0.0000 (6)	0.0072 (7)	−0.0070 (7)
C17	0.0282 (6)	0.0203 (6)	0.0174 (5)	0.0023 (5)	0.0102 (5)	−0.0032 (5)
C18	0.0363 (7)	0.0271 (7)	0.0188 (6)	−0.0016 (6)	0.0066 (5)	−0.0020 (5)
C19	0.0322 (8)	0.0571 (11)	0.0409 (9)	0.0112 (7)	0.0119 (7)	−0.0200 (8)
C20	0.0704 (11)	0.0197 (7)	0.0252 (7)	−0.0065 (7)	0.0235 (7)	−0.0064 (5)
C21	0.0242 (6)	0.0335 (8)	0.0437 (9)	0.0012 (6)	0.0095 (6)	0.0084 (7)

Geometric parameters (Å, º) top

O1—C11	1.3536 (15)	C10—C11	1.3827 (18)
O1—H1O1	0.857 (19)	C10—H10A	0.9300
O2—C12	1.3672 (15)	C11—C12	1.4060 (17)
O2—C21	1.4235 (17)	C12—C13	1.3941 (17)
O3—C14	1.2104 (17)	C13—H13A	0.9300
O4—C14	1.3424 (18)	C15—C16	1.500 (2)
O4—C15	1.4563 (17)	C15—H15A	0.9700
N1—C7	1.3193 (16)	C15—H15B	0.9700
N1—C1	1.3815 (16)	C16—H16A	0.9600
N2—C7	1.3890 (16)	C16—H16B	0.9600
N2—C6	1.3958 (16)	C16—H16C	0.9600
N2—C17	1.5086 (16)	C17—C19	1.523 (2)
C1—C2	1.3945 (17)	C17—C20	1.525 (2)
C1—C6	1.4010 (17)	C17—C18	1.5278 (18)
C2—C3	1.3885 (18)	C18—H18A	0.9600
C2—H2A	0.9300	C18—H18B	0.9600
C3—C4	1.4027 (19)	C18—H18C	0.9600
C3—C14	1.4871 (19)	C19—H19A	0.9600
C4—C5	1.384 (2)	C19—H19B	0.9600
C4—H4A	0.9300	C19—H19C	0.9600
C5—C6	1.3995 (18)	C20—H20A	0.9600
C5—H5A	0.9300	C20—H20B	0.9600
C7—C8	1.4858 (17)	C20—H20C	0.9600
C8—C9	1.3903 (18)	C21—H21A	0.9600
C8—C13	1.3918 (18)	C21—H21B	0.9600
C9—C10	1.3860 (18)	C21—H21C	0.9600
C9—H9A	0.9300

C11—O1—H1O1	111.5 (13)	O3—C14—O4	123.26 (13)
C12—O2—C21	117.31 (11)	O3—C14—C3	124.66 (14)
C14—O4—C15	116.70 (11)	O4—C14—C3	112.08 (11)
C7—N1—C1	105.49 (10)	O4—C15—C16	106.30 (12)
C7—N2—C6	105.36 (10)	O4—C15—H15A	110.5
C7—N2—C17	130.51 (11)	C16—C15—H15A	110.5
C6—N2—C17	124.12 (10)	O4—C15—H15B	110.5
N1—C1—C2	128.17 (12)	C16—C15—H15B	110.5
N1—C1—C6	110.05 (11)	H15A—C15—H15B	108.7
C2—C1—C6	121.60 (12)	C15—C16—H16A	109.5
C3—C2—C1	118.01 (12)	C15—C16—H16B	109.5
C3—C2—H2A	121.0	H16A—C16—H16B	109.5
C1—C2—H2A	121.0	C15—C16—H16C	109.5
C2—C3—C4	120.21 (12)	H16A—C16—H16C	109.5
C2—C3—C14	121.30 (12)	H16B—C16—H16C	109.5
C4—C3—C14	118.49 (12)	N2—C17—C19	108.35 (11)
C5—C4—C3	122.17 (13)	N2—C17—C20	112.42 (10)
C5—C4—H4A	118.9	C19—C17—C20	109.53 (13)
C3—C4—H4A	118.9	N2—C17—C18	108.80 (11)
C4—C5—C6	117.65 (13)	C19—C17—C18	111.05 (12)
C4—C5—H5A	121.2	C20—C17—C18	106.70 (11)
C6—C5—H5A	121.2	C17—C18—H18A	109.5
N2—C6—C5	133.58 (12)	C17—C18—H18B	109.5
N2—C6—C1	105.99 (10)	H18A—C18—H18B	109.5
C5—C6—C1	120.33 (12)	C17—C18—H18C	109.5
N1—C7—N2	113.08 (11)	H18A—C18—H18C	109.5
N1—C7—C8	120.63 (11)	H18B—C18—H18C	109.5
N2—C7—C8	125.63 (11)	C17—C19—H19A	109.5
C9—C8—C13	119.80 (12)	C17—C19—H19B	109.5
C9—C8—C7	117.19 (11)	H19A—C19—H19B	109.5
C13—C8—C7	122.98 (11)	C17—C19—H19C	109.5
C10—C9—C8	120.41 (12)	H19A—C19—H19C	109.5
C10—C9—H9A	119.8	H19B—C19—H19C	109.5
C8—C9—H9A	119.8	C17—C20—H20A	109.5
C11—C10—C9	120.65 (12)	C17—C20—H20B	109.5
C11—C10—H10A	119.7	H20A—C20—H20B	109.5
C9—C10—H10A	119.7	C17—C20—H20C	109.5
O1—C11—C10	118.45 (11)	H20A—C20—H20C	109.5
O1—C11—C12	122.49 (11)	H20B—C20—H20C	109.5
C10—C11—C12	119.04 (12)	O2—C21—H21A	109.5
O2—C12—C13	125.21 (11)	O2—C21—H21B	109.5
O2—C12—C11	114.33 (11)	H21A—C21—H21B	109.5
C13—C12—C11	120.45 (12)	O2—C21—H21C	109.5
C8—C13—C12	119.62 (12)	H21A—C21—H21C	109.5
C8—C13—H13A	120.2	H21B—C21—H21C	109.5
C12—C13—H13A	120.2

C7—N1—C1—C2	−174.69 (13)	C13—C8—C9—C10	1.40 (19)
C7—N1—C1—C6	0.37 (14)	C7—C8—C9—C10	179.51 (11)
N1—C1—C2—C3	175.59 (12)	C8—C9—C10—C11	0.46 (19)
C6—C1—C2—C3	1.04 (19)	C9—C10—C11—O1	177.51 (11)
C1—C2—C3—C4	0.06 (19)	C9—C10—C11—C12	−1.22 (19)
C1—C2—C3—C14	−179.51 (11)	C21—O2—C12—C13	1.43 (19)
C2—C3—C4—C5	−1.6 (2)	C21—O2—C12—C11	−177.52 (12)
C14—C3—C4—C5	177.98 (13)	O1—C11—C12—O2	0.46 (17)
C3—C4—C5—C6	2.0 (2)	C10—C11—C12—O2	179.14 (11)
C7—N2—C6—C5	174.74 (14)	O1—C11—C12—C13	−178.54 (11)
C17—N2—C6—C5	−4.1 (2)	C10—C11—C12—C13	0.14 (18)
C7—N2—C6—C1	−1.55 (13)	C9—C8—C13—C12	−2.46 (18)
C17—N2—C6—C1	179.58 (11)	C7—C8—C13—C12	179.55 (11)
C4—C5—C6—N2	−176.68 (13)	O2—C12—C13—C8	−177.19 (11)
C4—C5—C6—C1	−0.82 (19)	C11—C12—C13—C8	1.70 (18)
N1—C1—C6—N2	0.77 (14)	C15—O4—C14—O3	0.3 (2)
C2—C1—C6—N2	176.21 (11)	C15—O4—C14—C3	−179.85 (11)
N1—C1—C6—C5	−176.11 (12)	C2—C3—C14—O3	−165.35 (13)
C2—C1—C6—C5	−0.67 (19)	C4—C3—C14—O3	15.1 (2)
C1—N1—C7—N2	−1.44 (14)	C2—C3—C14—O4	14.78 (18)
C1—N1—C7—C8	169.72 (11)	C4—C3—C14—O4	−164.80 (12)
C6—N2—C7—N1	1.92 (14)	C14—O4—C15—C16	178.47 (12)
C17—N2—C7—N1	−179.30 (11)	C7—N2—C17—C19	−108.89 (16)
C6—N2—C7—C8	−168.71 (12)	C6—N2—C17—C19	69.69 (16)
C17—N2—C7—C8	10.1 (2)	C7—N2—C17—C20	12.30 (18)
N1—C7—C8—C9	−86.62 (15)	C6—N2—C17—C20	−169.12 (12)
N2—C7—C8—C9	83.36 (16)	C7—N2—C17—C18	130.27 (13)
N1—C7—C8—C13	91.42 (16)	C6—N2—C17—C18	−51.15 (16)
N2—C7—C8—C13	−98.60 (16)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C8–C13 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1ⁱ	0.85 (2)	1.97 (2)	2.7475 (17)	151.7 (19)
C2—H2A···O2ⁱⁱ	0.93	2.58	3.3648 (17)	142
C13—H13A···O3ⁱⁱⁱ	0.93	2.56	3.4223 (17)	154
C18—H18B···O4ⁱⁱⁱ	0.96	2.60	3.514 (2)	160
C18—H18C···O1^iv	0.96	2.54	3.4753 (17)	163
C18—H18A···Cg1^v	0.96	2.89	3.5798 (16)	129
C20—H20B···Cg1	0.96	2.81	3.4764 (17)	127

Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) −x, y+1/2, −z+3/2; (iii) −x, −y+1, −z+1; (iv) −x, −y, −z+1; (v) x, −y−1/2, z−3/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₄N₂O₄
M_r	368.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.2610 (6), 13.6096 (9), 16.3200 (9)
β (°)	113.560 (3)
V (Å³)	1885.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.38 × 0.23 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.967, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	21041, 5484, 4104
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.134, 1.07
No. of reflections	5484
No. of parameters	253
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.38

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C8–C13 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1ⁱ	0.85 (2)	1.97 (2)	2.7475 (17)	151.7 (19)
C2—H2A···O2ⁱⁱ	0.9300	2.5800	3.3648 (17)	142.00
C13—H13A···O3ⁱⁱⁱ	0.9300	2.5600	3.4223 (17)	154.00
C18—H18B···O4ⁱⁱⁱ	0.9600	2.6000	3.514 (2)	160.00
C18—H18C···O1^iv	0.9600	2.5400	3.4753 (17)	163.00
C18—H18A···Cg1^v	0.9600	2.8900	3.5798 (16)	129.00
C20—H20B···Cg1	0.9600	2.8100	3.4764 (17)	127.00

Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) −x, y+1/2, −z+3/2; (iii) −x, −y+1, −z+1; (iv) −x, −y, −z+1; (v) x, −y−1/2, z−3/2.

Footnotes

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

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

NA, ASAR and HO gratefully acknowledge Universiti Sains Malaysia (USM) for funding the synthetic chemistry work under the USM Research University Grant (1001/PFARMASI/815026). NA thanks Universiti Sains Malaysia for the award of a postdoctoral fellowship. HKF and MMR thank Universiti Sains Malaysia for the Research University Golden Goose grant (No. 1001/PFIZIK/811012).

References

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Volume 66| Part 5| May 2010| Pages o1051-o1052

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

Ethyl 1-tert-butyl-2-(4-hydr­­oxy-3-meth­oxy­phen­yl)-1H-benzimidazole-5-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

Ethyl 1-tert-butyl-2-(4-hydroxy-3-methoxyphenyl)-1H-benzimidazole-5-carboxylate