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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1590–o1591.
Published online 2010 June 5. doi:  10.1107/S1600536810020799
PMCID: PMC3006903

Ethyl 1-(2-hy­droxy­eth­yl)-2-p-tolyl-1H-benzimidazole-5-carboxyl­ate

Abstract

The asymmetric unit of the title compound, C19H20N2O3, contains two mol­ecules (A and B) with slightly different orientations of the ethyl groups with respect to the attached carboxyl­ate groups. Intra­molecular C—H(...)O hydrogen bonds generate S(8) ring motifs in both mol­ecules A and B. In each mol­ecule, the benzimidazole ring system is essentially planar, with maximum deviations of 0.023 (1) and 0.020 (1) Å, respectively, for mol­ecules A and B. The dihedral angle between the benzimidazole ring system and the phenyl ring is 37.34 (5)° for mol­ecule A and 42.42 (5)° for mol­ecule B. In the crystal, O—H(...)N and C—H(...)O hydrogen bonds link the mol­ecules into [100] columns with a cross-section of two-mol­ecule by two-mol­ecule wide, and further stabilization is provided by weak C—H(...)π and π–π inter­actions [centroid separations = 3.5207 (7) and 3.6314 (8) Å].

Related literature

For general background to and applications of benzimidazole derivatives, see: Denny et al. (1990 [triangle]); Evans et al. (1997 [triangle]); Grassmann et al. (2002 [triangle]); Göker et al. (2002 [triangle]); Seth et al. (2003 [triangle]). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995 [triangle]). For closely related benzimidazole structures, see: Arumugam et al. (2010a [triangle],b [triangle],c [triangle]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1590-scheme1.jpg

Experimental

Crystal data

  • C19H20N2O3
  • M r = 324.37
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1590-efi1.jpg
  • a = 9.0400 (9) Å
  • b = 12.6806 (13) Å
  • c = 15.5504 (17) Å
  • α = 74.170 (2)°
  • β = 74.360 (2)°
  • γ = 76.721 (2)°
  • V = 1627.9 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 K
  • 0.41 × 0.32 × 0.23 mm

Data collection

  • Bruker APEXII DUO CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.964, T max = 0.980
  • 30776 measured reflections
  • 10646 independent reflections
  • 8773 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.194
  • S = 1.13
  • 10646 reflections
  • 445 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.60 e Å−3
  • Δρmin = −0.65 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020799/hb5474sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020799/hb5474Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

NA, ASAR and HAW acknowledge Universiti Sains Malaysia (USM) for funding the synthetic chemistry work under the USM Research University Grant (No. 1001/PFARMASI/815026) and the Ministry of Science, Technology and Innovations (MOSTI) Grant (No. 304/PFARMASI/650512/I121). NA also thanks USM for the award of a postdoctoral fellowship. HKF and JHG thank USM for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship.

supplementary crystallographic information

Comment

Benzimidazoles are known to exhibit anti-HIV (Evans et al., 1997), anti-fungal (Göker et al., 2002) and anti-parasitic (Seth et al., 2003) activities. In particular, substituted benzimidazoles have proven as drug leads, generating pharmacological interests (Grassmann et al., 2002). A series of substituted benzimidazole derivatives have been synthesised and evaluated for in vitro and in vivo anti-tumor activity and DNA binding affinity (Denny et al., 1990). Due to their importance, the crystal structure determination of the title compound was carried out and the results are presented in this paper.

The asymmetric unit of the title benzimidazole compound (Fig. 1) comprises of two crystallographically independent molecules, designated A and B. A superposition of the non-H atoms of molecules A and B (Fig. 2) using XP in SHELXTL (Sheldrick, 2008), gave an r.m.s. deviation of 0.517 Å. Molecules A and B differ slightly in the orientation of the ethyl groups (C15 and C16) with respect to the attached carboxylate groups, as can be seen in Fig. 2. The torsion angles C14A–O2A–C15A–C16A and C14B–O2B–C15B–C16B are -77.41 (15) and -171.37 (10)°, respectively.

Intramolecular C1A—H1AA···O3A and C1B—H1BA···O3B hydrogen bonds generate eight-membered rings, producing S(8) ring motifs (Bernstein, 1995). In each molecule, the benzimidazole ring system (C7-C13/N1/N2) are essentially planar, with maximum deviations of 0.023 (1) and -0.020 (1) Å, respectively, at atoms C7A of molecule A and C8B of molecule B. In molecule A, the benzimidazole ring system is inclined at dihedral angle of 37.34 (5)° with the C1A-C6A phenyl ring; the respective angle for molecule B is 42.42 (5)°. The geometric parameters are comparable to those reported in closely related benzimidazole structures (Arumugam et al., 2010a,b,c).

In the crystal packing (Fig. 3), intermolecular O3A—H1OA···N1B, O3B—H1OB···N1A, C12B—H12B···O3A, C15B—H15C···O1B and C18A—H18A···O1A hydrogen bonds link the molecules into columns with cross-section of two-molecule by two-molecule wide along the a axis. The crystal packing is further stabilized by intermolecular C17B—H17C···Cg1 interactions (Table 1) as well as weak π–π aromatic stacking interactions [Cg1···Cg2 = 3.5207 (7) and Cg3···Cg4 = 3.6314 (8) Å; symmetry code: x, y, z; Cg1 and Cg2 are the centroids of 4,5-dihydroimidazole rings (C7A/N1A/C8A/C13A/N2A and C7B/N1B/C8B/C13B/N2B), respectively; Cg3 and Cg4 are the centroids of C8A-C13A and C8B-C13B phenyl rings, respectively].

Experimental

A solution of ethyl-3-amino-4-(2-hydroxyethylamino) benzoate (0.5 g, 2.22 mmol) and sodium bisulfite adduct of p-methyl benzaldehyde (1.0 g, 4.46 mmol) in DMF was treated under microwave conditions at 403 K. The reaction mixture was then diluted in EtOAc (30 ml) and washed with H2O (30 ml). The organic layer was collected and dried over Na2SO4. The solvent was removed under reduced pressure to afford the crude product, which upon recrystallisation from EtOAc, revealed the title compound as colourless crystals.

Refinement

Hydroxy H-atoms were located from the difference Fourier map and allowed to refine freely. The remaining H atoms were place in their calculated positions, with C–H = 0.93–0.97 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). The rotating group model was applied for the methyl groups. The highest residual electron density peak is 0.49 Å from N2B and the deepest hole is 0.85 Å from C8B.

Figures

Fig. 1.
The molecular structure of (I) with 50% probability displacement ellipsoids for non-H atoms. Intramolecular hydrogen bonds are shown as dashed lines.
Fig. 2.
Fit of molecule A (dashed lines) on molecule B (solid lines). H atoms have been omitted for clarity.
Fig. 3.
The crystal packing of (I), viewed down c axis, showing a two-molecule by two-molecule wide column along the a axis. H atoms not involved in intermolecular interactions (dashed lines) have been omitted for clarity.

Crystal data

C19H20N2O3Z = 4
Mr = 324.37F(000) = 688
Triclinic, P1Dx = 1.324 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.0400 (9) ÅCell parameters from 9690 reflections
b = 12.6806 (13) Åθ = 2.8–33.8°
c = 15.5504 (17) ŵ = 0.09 mm1
α = 74.170 (2)°T = 100 K
β = 74.360 (2)°Block, colourless
γ = 76.721 (2)°0.41 × 0.32 × 0.23 mm
V = 1627.9 (3) Å3

Data collection

Bruker APEXII DUO CCD diffractometer10646 independent reflections
Radiation source: fine-focus sealed tube8773 reflections with I > 2σ(I)
graphiteRint = 0.030
[var phi] and ω scansθmax = 31.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −13→13
Tmin = 0.964, Tmax = 0.980k = −18→18
30776 measured reflectionsl = −22→22

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.194H atoms treated by a mixture of independent and constrained refinement
S = 1.13w = 1/[σ2(Fo2) + (0.1301P)2 + 0.1152P] where P = (Fo2 + 2Fc2)/3
10646 reflections(Δ/σ)max < 0.001
445 parametersΔρmax = 0.60 e Å3
0 restraintsΔρmin = −0.65 e Å3

Special details

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

xyzUiso*/Ueq
O1A0.07593 (12)0.34205 (9)0.46417 (7)0.0276 (2)
O2A0.22621 (11)0.21688 (8)0.55131 (7)0.0214 (2)
O3A0.96752 (10)0.50727 (7)0.18794 (6)0.01475 (17)
N1A0.44922 (12)0.63318 (8)0.29752 (7)0.01358 (19)
N2A0.68064 (11)0.55873 (8)0.33553 (6)0.01221 (18)
C1A0.79520 (14)0.76316 (10)0.18103 (8)0.0153 (2)
H1AA0.87060.69990.17720.018*
C2A0.83043 (14)0.86714 (10)0.13230 (8)0.0170 (2)
H2AA0.93020.87230.09650.020*
C3A0.72088 (14)0.96366 (10)0.13554 (8)0.0164 (2)
C4A0.57258 (15)0.95372 (10)0.19112 (8)0.0172 (2)
H4AA0.49771.01720.19530.021*
C5A0.53556 (14)0.85052 (10)0.24015 (8)0.0161 (2)
H5AA0.43600.84560.27630.019*
C6A0.64640 (13)0.75385 (9)0.23574 (8)0.0132 (2)
C7A0.59444 (13)0.64791 (9)0.28754 (7)0.0127 (2)
C8A0.43877 (13)0.52957 (9)0.35614 (7)0.0123 (2)
C9A0.31274 (13)0.47294 (9)0.39126 (8)0.0139 (2)
H9AA0.21760.50290.37480.017*
C10A0.33376 (14)0.37013 (9)0.45175 (8)0.0141 (2)
C11A0.47717 (14)0.32492 (10)0.47744 (8)0.0148 (2)
H11A0.48690.25670.51910.018*
C12A0.60436 (14)0.37979 (9)0.44210 (8)0.0141 (2)
H12A0.69960.34980.45840.017*
C13A0.58203 (13)0.48226 (9)0.38085 (7)0.0122 (2)
C14A0.19800 (15)0.31049 (10)0.48803 (8)0.0168 (2)
C15A0.09808 (16)0.15392 (11)0.59046 (10)0.0240 (3)
H15A0.13830.07840.61900.029*
H15B0.05220.15060.54180.029*
C16A−0.02486 (18)0.20524 (12)0.66008 (10)0.0256 (3)
H16A−0.10420.15960.68670.038*
H16B−0.07020.27800.63100.038*
H16C0.02090.21120.70720.038*
C17A0.84315 (13)0.53960 (9)0.34180 (8)0.0138 (2)
H17A0.85010.50880.40520.017*
H17B0.88060.61010.32210.017*
C18A0.94678 (13)0.46049 (10)0.28325 (8)0.0145 (2)
H18A1.04790.43870.29900.017*
H18B0.90110.39390.29750.017*
C19A0.75854 (17)1.07453 (11)0.07806 (10)0.0230 (3)
H19A0.86921.07220.06350.035*
H19B0.70821.13120.11160.035*
H19C0.72231.09090.02250.035*
O1B0.62907 (11)0.10394 (8)0.35690 (7)0.0212 (2)
O2B0.38151 (10)0.10387 (7)0.35342 (6)0.01744 (18)
O3B0.29192 (11)0.76162 (7)0.15387 (6)0.01769 (18)
N1B0.71022 (11)0.49118 (8)0.12914 (6)0.01173 (18)
N2B0.48235 (11)0.56326 (8)0.08697 (6)0.01134 (18)
C1B0.62243 (14)0.78327 (9)0.00981 (8)0.0148 (2)
H1BA0.52240.79900.04490.018*
C2B0.69291 (15)0.86841 (10)−0.05266 (9)0.0184 (2)
H2BA0.63890.9410−0.05870.022*
C3B0.84224 (15)0.84821 (11)−0.10662 (8)0.0196 (2)
C4B0.92369 (15)0.73979 (11)−0.09289 (9)0.0192 (2)
H4BA1.02550.7250−0.12600.023*
C5B0.85548 (14)0.65327 (10)−0.03060 (8)0.0158 (2)
H5BA0.91190.5814−0.02240.019*
C6B0.70215 (13)0.67365 (9)0.01996 (7)0.0123 (2)
C7B0.63190 (12)0.57798 (9)0.08024 (7)0.01131 (19)
C8B0.60714 (12)0.41630 (9)0.17018 (7)0.01138 (19)
C9B0.62468 (13)0.31246 (9)0.22990 (7)0.0124 (2)
H9BA0.71730.28210.24930.015*
C10B0.49860 (13)0.25547 (9)0.25962 (7)0.0128 (2)
C11B0.35857 (13)0.29980 (9)0.22970 (8)0.0138 (2)
H11B0.27790.25860.24960.017*
C12B0.33878 (13)0.40355 (9)0.17128 (8)0.0130 (2)
H12B0.24650.43370.15150.016*
C13B0.46462 (12)0.46028 (9)0.14371 (7)0.01133 (19)
C14B0.51372 (13)0.14745 (9)0.32729 (8)0.0141 (2)
C15B0.38024 (15)0.00252 (10)0.42410 (9)0.0191 (2)
H15C0.38120.01740.48190.023*
H15D0.4716−0.05180.40780.023*
C16B0.23432 (17)−0.04128 (12)0.43262 (10)0.0253 (3)
H16D0.2266−0.10570.48220.038*
H16E0.2383−0.06110.37660.038*
H16F0.14510.01500.44450.038*
C17B0.35660 (13)0.63748 (9)0.04793 (8)0.0135 (2)
H17C0.30820.59610.02220.016*
H17D0.39900.6956−0.00140.016*
C18B0.23360 (13)0.69020 (10)0.11993 (8)0.0159 (2)
H18C0.14640.73220.09320.019*
H18D0.19530.63180.17060.019*
C19B0.9105 (2)0.94054 (13)−0.17975 (10)0.0301 (3)
H19D1.02200.9215−0.19360.045*
H19E0.88011.0081−0.15820.045*
H19F0.87260.9508−0.23400.045*
H1OA0.875 (3)0.5068 (18)0.1692 (14)0.039 (6)*
H1OB0.328 (3)0.7248 (19)0.1973 (15)0.035 (5)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0201 (5)0.0313 (5)0.0292 (5)−0.0108 (4)−0.0094 (4)0.0060 (4)
O2A0.0170 (4)0.0157 (4)0.0259 (5)−0.0055 (3)−0.0013 (3)0.0032 (3)
O3A0.0102 (4)0.0206 (4)0.0134 (4)−0.0030 (3)−0.0024 (3)−0.0036 (3)
N1A0.0129 (4)0.0138 (4)0.0123 (4)−0.0020 (3)−0.0024 (3)−0.0008 (3)
N2A0.0108 (4)0.0132 (4)0.0113 (4)−0.0018 (3)−0.0021 (3)−0.0011 (3)
C1A0.0133 (5)0.0140 (5)0.0164 (5)−0.0012 (4)−0.0024 (4)−0.0016 (4)
C2A0.0141 (5)0.0154 (5)0.0187 (5)−0.0029 (4)−0.0031 (4)0.0004 (4)
C3A0.0182 (5)0.0140 (5)0.0173 (5)−0.0029 (4)−0.0062 (4)−0.0014 (4)
C4A0.0183 (5)0.0131 (5)0.0187 (5)0.0011 (4)−0.0047 (4)−0.0037 (4)
C5A0.0153 (5)0.0151 (5)0.0167 (5)−0.0008 (4)−0.0027 (4)−0.0041 (4)
C6A0.0129 (5)0.0132 (5)0.0124 (5)−0.0016 (4)−0.0028 (4)−0.0018 (4)
C7A0.0120 (5)0.0128 (5)0.0120 (4)−0.0009 (4)−0.0020 (4)−0.0024 (4)
C8A0.0122 (5)0.0130 (5)0.0106 (4)−0.0016 (4)−0.0017 (4)−0.0020 (4)
C9A0.0117 (5)0.0155 (5)0.0134 (5)−0.0020 (4)−0.0020 (4)−0.0026 (4)
C10A0.0148 (5)0.0145 (5)0.0121 (5)−0.0035 (4)−0.0009 (4)−0.0027 (4)
C11A0.0150 (5)0.0144 (5)0.0132 (5)−0.0023 (4)−0.0020 (4)−0.0011 (4)
C12A0.0127 (5)0.0145 (5)0.0131 (5)−0.0008 (4)−0.0029 (4)−0.0012 (4)
C13A0.0119 (5)0.0130 (5)0.0103 (4)−0.0017 (4)−0.0008 (3)−0.0023 (4)
C14A0.0177 (5)0.0167 (5)0.0149 (5)−0.0049 (4)−0.0017 (4)−0.0021 (4)
C15A0.0205 (6)0.0164 (5)0.0307 (7)−0.0084 (4)0.0015 (5)−0.0008 (5)
C16A0.0277 (7)0.0268 (6)0.0219 (6)−0.0118 (5)−0.0004 (5)−0.0035 (5)
C17A0.0117 (5)0.0163 (5)0.0137 (5)−0.0020 (4)−0.0038 (4)−0.0031 (4)
C18A0.0116 (5)0.0164 (5)0.0142 (5)−0.0001 (4)−0.0041 (4)−0.0021 (4)
C19A0.0263 (7)0.0144 (5)0.0257 (6)−0.0042 (5)−0.0074 (5)0.0022 (5)
O1B0.0168 (4)0.0184 (4)0.0249 (5)−0.0033 (3)−0.0078 (4)0.0044 (3)
O2B0.0155 (4)0.0163 (4)0.0181 (4)−0.0053 (3)−0.0037 (3)0.0021 (3)
O3B0.0189 (4)0.0150 (4)0.0177 (4)−0.0003 (3)−0.0036 (3)−0.0039 (3)
N1B0.0096 (4)0.0128 (4)0.0121 (4)−0.0017 (3)−0.0029 (3)−0.0013 (3)
N2B0.0092 (4)0.0110 (4)0.0126 (4)−0.0003 (3)−0.0035 (3)−0.0009 (3)
C1B0.0140 (5)0.0136 (5)0.0165 (5)−0.0008 (4)−0.0053 (4)−0.0023 (4)
C2B0.0203 (6)0.0148 (5)0.0206 (6)−0.0038 (4)−0.0089 (4)0.0003 (4)
C3B0.0213 (6)0.0207 (6)0.0174 (5)−0.0093 (4)−0.0068 (4)0.0021 (4)
C4B0.0142 (5)0.0233 (6)0.0176 (5)−0.0059 (4)−0.0003 (4)−0.0016 (4)
C5B0.0126 (5)0.0171 (5)0.0161 (5)−0.0023 (4)−0.0023 (4)−0.0021 (4)
C6B0.0110 (5)0.0138 (5)0.0117 (4)−0.0021 (4)−0.0038 (4)−0.0011 (4)
C7B0.0091 (4)0.0129 (5)0.0116 (4)−0.0013 (3)−0.0022 (3)−0.0028 (4)
C8B0.0092 (4)0.0137 (5)0.0111 (4)−0.0015 (3)−0.0020 (3)−0.0031 (4)
C9B0.0098 (4)0.0145 (5)0.0124 (5)−0.0004 (3)−0.0031 (4)−0.0030 (4)
C10B0.0121 (5)0.0130 (5)0.0121 (5)−0.0013 (4)−0.0020 (4)−0.0024 (4)
C11B0.0120 (5)0.0145 (5)0.0143 (5)−0.0027 (4)−0.0027 (4)−0.0020 (4)
C12B0.0100 (5)0.0151 (5)0.0137 (5)−0.0019 (4)−0.0034 (4)−0.0027 (4)
C13B0.0100 (4)0.0123 (4)0.0113 (4)−0.0011 (3)−0.0028 (3)−0.0023 (4)
C14B0.0135 (5)0.0144 (5)0.0137 (5)−0.0027 (4)−0.0021 (4)−0.0025 (4)
C15B0.0195 (6)0.0163 (5)0.0188 (5)−0.0061 (4)−0.0048 (4)0.0033 (4)
C16B0.0210 (6)0.0237 (6)0.0298 (7)−0.0086 (5)−0.0022 (5)−0.0032 (5)
C17B0.0108 (5)0.0134 (5)0.0157 (5)0.0008 (4)−0.0063 (4)−0.0013 (4)
C18B0.0107 (5)0.0154 (5)0.0196 (5)0.0004 (4)−0.0032 (4)−0.0028 (4)
C19B0.0342 (8)0.0284 (7)0.0255 (7)−0.0173 (6)−0.0068 (6)0.0079 (5)

Geometric parameters (Å, °)

O1A—C14A1.2051 (17)O1B—C14B1.2082 (15)
O2A—C14A1.3422 (15)O2B—C14B1.3483 (14)
O2A—C15A1.4591 (15)O2B—C15B1.4454 (14)
O3A—C18A1.4160 (14)O3B—C18B1.4166 (15)
O3A—H1OA0.96 (2)O3B—H1OB0.81 (2)
N1A—C7A1.3302 (15)N1B—C7B1.3291 (14)
N1A—C8A1.3868 (14)N1B—C8B1.3902 (13)
N2A—C7A1.3752 (15)N2B—C13B1.3787 (14)
N2A—C13A1.3846 (14)N2B—C7B1.3793 (14)
N2A—C17A1.4586 (15)N2B—C17B1.4545 (14)
C1A—C2A1.3899 (16)C1B—C2B1.3875 (16)
C1A—C6A1.3959 (16)C1B—C6B1.3993 (16)
C1A—H1AA0.9300C1B—H1BA0.9300
C2A—C3A1.3896 (17)C2B—C3B1.3928 (18)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.3978 (17)C3B—C4B1.3919 (19)
C3A—C19A1.5038 (17)C3B—C19B1.5072 (18)
C4A—C5A1.3875 (16)C4B—C5B1.3896 (16)
C4A—H4AA0.9300C4B—H4BA0.9300
C5A—C6A1.3985 (16)C5B—C6B1.4017 (16)
C5A—H5AA0.9300C5B—H5BA0.9300
C6A—C7A1.4729 (15)C6B—C7B1.4718 (15)
C8A—C9A1.3923 (15)C8B—C9B1.3919 (15)
C8A—C13A1.4037 (16)C8B—C13B1.4039 (15)
C9A—C10A1.3906 (16)C9B—C10B1.3954 (15)
C9A—H9AA0.9300C9B—H9BA0.9300
C10A—C11A1.4078 (17)C10B—C11B1.4082 (16)
C10A—C14A1.4889 (16)C10B—C14B1.4858 (16)
C11A—C12A1.3879 (15)C11B—C12B1.3840 (16)
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.3945 (16)C12B—C13B1.3929 (14)
C12A—H12A0.9300C12B—H12B0.9300
C15A—C16A1.495 (2)C15B—C16B1.5060 (18)
C15A—H15A0.9700C15B—H15C0.9700
C15A—H15B0.9700C15B—H15D0.9700
C16A—H16A0.9600C16B—H16D0.9600
C16A—H16B0.9600C16B—H16E0.9600
C16A—H16C0.9600C16B—H16F0.9600
C17A—C18A1.5230 (16)C17B—C18B1.5272 (16)
C17A—H17A0.9700C17B—H17C0.9700
C17A—H17B0.9700C17B—H17D0.9700
C18A—H18A0.9700C18B—H18C0.9700
C18A—H18B0.9700C18B—H18D0.9700
C19A—H19A0.9600C19B—H19D0.9600
C19A—H19B0.9600C19B—H19E0.9600
C19A—H19C0.9600C19B—H19F0.9600
C14A—O2A—C15A115.51 (11)C14B—O2B—C15B116.22 (10)
C18A—O3A—H1OA108.5 (13)C18B—O3B—H1OB108.2 (15)
C7A—N1A—C8A105.16 (10)C7B—N1B—C8B105.51 (9)
C7A—N2A—C13A106.47 (9)C13B—N2B—C7B107.03 (9)
C7A—N2A—C17A130.53 (9)C13B—N2B—C17B122.50 (9)
C13A—N2A—C17A123.00 (10)C7B—N2B—C17B130.43 (10)
C2A—C1A—C6A119.88 (11)C2B—C1B—C6B119.85 (11)
C2A—C1A—H1AA120.1C2B—C1B—H1BA120.1
C6A—C1A—H1AA120.1C6B—C1B—H1BA120.1
C3A—C2A—C1A121.93 (11)C1B—C2B—C3B121.82 (12)
C3A—C2A—H2AA119.0C1B—C2B—H2BA119.1
C1A—C2A—H2AA119.0C3B—C2B—H2BA119.1
C2A—C3A—C4A117.82 (11)C4B—C3B—C2B117.94 (11)
C2A—C3A—C19A121.07 (11)C4B—C3B—C19B121.33 (12)
C4A—C3A—C19A121.05 (11)C2B—C3B—C19B120.70 (13)
C5A—C4A—C3A120.93 (11)C5B—C4B—C3B121.13 (11)
C5A—C4A—H4AA119.5C5B—C4B—H4BA119.4
C3A—C4A—H4AA119.5C3B—C4B—H4BA119.4
C4A—C5A—C6A120.73 (11)C4B—C5B—C6B120.40 (11)
C4A—C5A—H5AA119.6C4B—C5B—H5BA119.8
C6A—C5A—H5AA119.6C6B—C5B—H5BA119.8
C1A—C6A—C5A118.69 (10)C1B—C6B—C5B118.70 (10)
C1A—C6A—C7A124.55 (10)C1B—C6B—C7B123.14 (10)
C5A—C6A—C7A116.72 (10)C5B—C6B—C7B118.15 (10)
N1A—C7A—N2A112.70 (10)N1B—C7B—N2B112.04 (9)
N1A—C7A—C6A121.20 (10)N1B—C7B—C6B123.42 (10)
N2A—C7A—C6A125.93 (10)N2B—C7B—C6B124.34 (10)
N1A—C8A—C9A129.96 (11)N1B—C8B—C9B130.89 (10)
N1A—C8A—C13A109.82 (10)N1B—C8B—C13B109.62 (10)
C9A—C8A—C13A120.21 (10)C9B—C8B—C13B119.49 (10)
C10A—C9A—C8A117.82 (11)C8B—C9B—C10B117.73 (10)
C10A—C9A—H9AA121.1C8B—C9B—H9BA121.1
C8A—C9A—H9AA121.1C10B—C9B—H9BA121.1
C9A—C10A—C11A121.28 (11)C9B—C10B—C11B121.69 (10)
C9A—C10A—C14A117.03 (11)C9B—C10B—C14B117.90 (10)
C11A—C10A—C14A121.70 (11)C11B—C10B—C14B120.37 (10)
C12A—C11A—C10A121.52 (11)C12B—C11B—C10B121.18 (10)
C12A—C11A—H11A119.2C12B—C11B—H11B119.4
C10A—C11A—H11A119.2C10B—C11B—H11B119.4
C11A—C12A—C13A116.56 (11)C11B—C12B—C13B116.38 (10)
C11A—C12A—H12A121.7C11B—C12B—H12B121.8
C13A—C12A—H12A121.7C13B—C12B—H12B121.8
N2A—C13A—C12A131.53 (11)N2B—C13B—C12B130.72 (10)
N2A—C13A—C8A105.85 (10)N2B—C13B—C8B105.80 (9)
C12A—C13A—C8A122.58 (10)C12B—C13B—C8B123.46 (10)
O1A—C14A—O2A123.30 (11)O1B—C14B—O2B123.54 (11)
O1A—C14A—C10A124.42 (12)O1B—C14B—C10B124.61 (11)
O2A—C14A—C10A112.29 (11)O2B—C14B—C10B111.84 (10)
O2A—C15A—C16A111.79 (11)O2B—C15B—C16B107.68 (11)
O2A—C15A—H15A109.3O2B—C15B—H15C110.2
C16A—C15A—H15A109.3C16B—C15B—H15C110.2
O2A—C15A—H15B109.3O2B—C15B—H15D110.2
C16A—C15A—H15B109.3C16B—C15B—H15D110.2
H15A—C15A—H15B107.9H15C—C15B—H15D108.5
C15A—C16A—H16A109.5C15B—C16B—H16D109.5
C15A—C16A—H16B109.5C15B—C16B—H16E109.5
H16A—C16A—H16B109.5H16D—C16B—H16E109.5
C15A—C16A—H16C109.5C15B—C16B—H16F109.5
H16A—C16A—H16C109.5H16D—C16B—H16F109.5
H16B—C16A—H16C109.5H16E—C16B—H16F109.5
N2A—C17A—C18A112.15 (9)N2B—C17B—C18B111.50 (9)
N2A—C17A—H17A109.2N2B—C17B—H17C109.3
C18A—C17A—H17A109.2C18B—C17B—H17C109.3
N2A—C17A—H17B109.2N2B—C17B—H17D109.3
C18A—C17A—H17B109.2C18B—C17B—H17D109.3
H17A—C17A—H17B107.9H17C—C17B—H17D108.0
O3A—C18A—C17A113.28 (9)O3B—C18B—C17B112.66 (9)
O3A—C18A—H18A108.9O3B—C18B—H18C109.1
C17A—C18A—H18A108.9C17B—C18B—H18C109.1
O3A—C18A—H18B108.9O3B—C18B—H18D109.1
C17A—C18A—H18B108.9C17B—C18B—H18D109.1
H18A—C18A—H18B107.7H18C—C18B—H18D107.8
C3A—C19A—H19A109.5C3B—C19B—H19D109.5
C3A—C19A—H19B109.5C3B—C19B—H19E109.5
H19A—C19A—H19B109.5H19D—C19B—H19E109.5
C3A—C19A—H19C109.5C3B—C19B—H19F109.5
H19A—C19A—H19C109.5H19D—C19B—H19F109.5
H19B—C19A—H19C109.5H19E—C19B—H19F109.5
C6A—C1A—C2A—C3A−0.49 (18)C6B—C1B—C2B—C3B0.21 (18)
C1A—C2A—C3A—C4A1.04 (18)C1B—C2B—C3B—C4B−3.33 (18)
C1A—C2A—C3A—C19A−176.41 (11)C1B—C2B—C3B—C19B174.55 (12)
C2A—C3A—C4A—C5A−1.06 (18)C2B—C3B—C4B—C5B3.20 (19)
C19A—C3A—C4A—C5A176.39 (11)C19B—C3B—C4B—C5B−174.67 (12)
C3A—C4A—C5A—C6A0.55 (18)C3B—C4B—C5B—C6B0.03 (19)
C2A—C1A—C6A—C5A−0.06 (17)C2B—C1B—C6B—C5B3.06 (17)
C2A—C1A—C6A—C7A177.64 (11)C2B—C1B—C6B—C7B−175.93 (11)
C4A—C5A—C6A—C1A0.03 (17)C4B—C5B—C6B—C1B−3.18 (17)
C4A—C5A—C6A—C7A−177.85 (11)C4B—C5B—C6B—C7B175.86 (11)
C8A—N1A—C7A—N2A0.84 (12)C8B—N1B—C7B—N2B−0.29 (12)
C8A—N1A—C7A—C6A−174.66 (9)C8B—N1B—C7B—C6B−175.30 (10)
C13A—N2A—C7A—N1A−1.15 (12)C13B—N2B—C7B—N1B−0.12 (12)
C17A—N2A—C7A—N1A178.46 (10)C17B—N2B—C7B—N1B177.66 (10)
C13A—N2A—C7A—C6A174.10 (10)C13B—N2B—C7B—C6B174.83 (10)
C17A—N2A—C7A—C6A−6.29 (18)C17B—N2B—C7B—C6B−7.39 (17)
C1A—C6A—C7A—N1A−144.30 (12)C1B—C6B—C7B—N1B−142.71 (11)
C5A—C6A—C7A—N1A33.45 (15)C5B—C6B—C7B—N1B38.29 (15)
C1A—C6A—C7A—N2A40.83 (17)C1B—C6B—C7B—N2B42.90 (16)
C5A—C6A—C7A—N2A−141.43 (11)C5B—C6B—C7B—N2B−136.10 (11)
C7A—N1A—C8A—C9A178.75 (11)C7B—N1B—C8B—C9B−178.72 (11)
C7A—N1A—C8A—C13A−0.21 (12)C7B—N1B—C8B—C13B0.59 (12)
N1A—C8A—C9A—C10A−178.00 (10)N1B—C8B—C9B—C10B−179.58 (10)
C13A—C8A—C9A—C10A0.88 (16)C13B—C8B—C9B—C10B1.16 (15)
C8A—C9A—C10A—C11A0.54 (16)C8B—C9B—C10B—C11B0.93 (16)
C8A—C9A—C10A—C14A−179.57 (10)C8B—C9B—C10B—C14B−176.73 (9)
C9A—C10A—C11A—C12A−1.38 (17)C9B—C10B—C11B—C12B−1.80 (17)
C14A—C10A—C11A—C12A178.74 (10)C14B—C10B—C11B—C12B175.80 (10)
C10A—C11A—C12A—C13A0.71 (16)C10B—C11B—C12B—C13B0.48 (16)
C7A—N2A—C13A—C12A−176.79 (11)C7B—N2B—C13B—C12B−178.09 (11)
C17A—N2A—C13A—C12A3.56 (18)C17B—N2B—C13B—C12B3.91 (17)
C7A—N2A—C13A—C8A0.93 (11)C7B—N2B—C13B—C8B0.47 (11)
C17A—N2A—C13A—C8A−178.72 (9)C17B—N2B—C13B—C8B−177.53 (9)
C11A—C12A—C13A—N2A178.14 (11)C11B—C12B—C13B—N2B−179.96 (11)
C11A—C12A—C13A—C8A0.75 (16)C11B—C12B—C13B—C8B1.69 (16)
N1A—C8A—C13A—N2A−0.46 (12)N1B—C8B—C13B—N2B−0.67 (12)
C9A—C8A—C13A—N2A−179.55 (9)C9B—C8B—C13B—N2B178.74 (9)
N1A—C8A—C13A—C12A177.51 (10)N1B—C8B—C13B—C12B178.03 (9)
C9A—C8A—C13A—C12A−1.57 (17)C9B—C8B—C13B—C12B−2.56 (16)
C15A—O2A—C14A—O1A0.05 (18)C15B—O2B—C14B—O1B3.17 (17)
C15A—O2A—C14A—C10A179.75 (10)C15B—O2B—C14B—C10B−175.76 (9)
C9A—C10A—C14A—O1A4.82 (18)C9B—C10B—C14B—O1B−1.86 (17)
C11A—C10A—C14A—O1A−175.29 (12)C11B—C10B—C14B—O1B−179.55 (11)
C9A—C10A—C14A—O2A−174.87 (10)C9B—C10B—C14B—O2B177.06 (9)
C11A—C10A—C14A—O2A5.02 (16)C11B—C10B—C14B—O2B−0.64 (15)
C14A—O2A—C15A—C16A−77.41 (15)C14B—O2B—C15B—C16B−171.37 (10)
C7A—N2A—C17A—C18A−102.64 (13)C13B—N2B—C17B—C18B73.62 (13)
C13A—N2A—C17A—C18A76.92 (13)C7B—N2B—C17B—C18B−103.86 (13)
N2A—C17A—C18A—O3A70.06 (12)N2B—C17B—C18B—O3B65.15 (12)

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1B/C7B/N2B/C8B/C13B 4,5-dihydro imidazole ring.
D—H···AD—HH···AD···AD—H···A
O3A—H1OA···N1B0.96 (3)1.83 (3)2.7847 (14)173 (2)
O3B—H1OB···N1A0.81 (2)2.08 (2)2.8859 (15)172 (3)
C1A—H1AA···O3A0.932.373.2473 (16)156
C1B—H1BA···O3B0.932.363.2331 (16)157
C12B—H12B···O3Ai0.932.453.2788 (16)149
C15B—H15C···O1Bii0.972.553.2889 (17)133
C18A—H18A···O1Aiii0.972.583.1928 (16)121
C17B—H17C···Cg1iv0.972.703.4194 (13)131

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5474).

References

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