



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046065/ci2468sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046065/ci2468Isup2.hkl |
CCDC reference: 663823
The title compound was synthesized by adding 5-allyl-2-hydroxy-3-methoxybenzaldehyde (0.216 g, 4 mmol) into a solution of o-phenylenediamine (0.216 g, 2 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for 0.5 h. Then zinc chloride (0.272 g, 2 mmol) in ethanol (10 ml) was added, followed by triethylamine (0.5 ml, 3.6 mmol). The mixture was stirred at room temperature for 2 h. The orange precipitate obtained was washed with about 5 ml e thanol, dried, and then washed with copious amounts of diethyl ether. Pale-yellow single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of the pyridine solution at room temperature after four weeks.
Hydroxyl H atoms were located in a difference map and refined isotropically. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with and C—H distances in the range 0.93–0.97 Å. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups.
The synthesis of benzimidazoles has received much attention owing to their various biological activities such as antidiabetic (Minoura et al., 2004), antimicrobial, antifungal (Pawar et al., 2004), antiviral (Tomei et al., 2003), anti-HIV (Barreca et al., 2003), and anticancer (Demirayak et al., 2002). Recently, we reported the crystal structures of 2-(benzimidazol-2-yl)-6-methoxyphenol (Eltayeb et al., 2007a) and 2-(2-methoxynaphthalen-1-yl)-1-[(2-methoxynaphthalen-1-yl)methyl]-1H- benzimidazole (Eltayeb et al., 2007b). The title compound was synthesized as an extension of our investigations of benzimidazole derivatives. We report here the crystal structure of the title compound.
The title compound crystalizes with two molecules of the benzimidazole derivative [A and B] and two molecules of pyridine in the asymmetric unit. In both A and B, the benzimidazole ring system is essentially planar. The benzimidazole ring system makes dihedral angles of 85.35 (5)° and 50.51 (5)°, respectively, with the C1–C6 and C15—C20 benzene rings in molecule A, and 82.93 (5)° and 51.30 (5)°, respectively, in molecule B. The hydroxyl groups are coplanar with the attached benzene rings, whereas the methoxy groups are slightly twisted away from the mean plane of the attached benzene rings, as indicated by the C25–O2–C2–C3 [4.29 (18)° in molecule A and 2.11 (18)° in molecule B] and C24–O4–C17–C18 [6.52 (19)° in molecule A and 12.40 (19) ° in molecule B] torsion angles. The orientation of the allyl groups with respect to the attached benzene rings can be described by the torsion angle C3–C4–C26–C27 of 104.09 (15)° in molecule A [-81.78 (16)° in molecule B] and C18–C19–C21–C22 torsion angle of 168.38 (12)° in molecule A [171.79 (12)° in molecule B]. Bond lengths and angles in both molecules are in normal ranges (Allen et al., 1987) and are comparable to those in related structures (Eltayeb et al., 2007a; 2007b).
There are two O—H···O intramolecular hydrogen bonds involving the two hydroxyl and the two methoxyl groups [O1A—H1OA···O2A and O3A—H3OA···O4A in molecule A, and O1B—H1OB···O2B and O3B—H3OB···O4B in molecule B] (Table 1) which generate S(6) ring motifs. In addition, C—H···O intramolecular hydrogen bonds are also observed.
The crystal structure is stabilized by intermolecular O—H···N and C—H···O hydrogen bonds, which link the molecules into chains along the [1 1 0] direction (Fig. 2). The structure is further stabilized by intermolecular C—H···π interactions (Table 1), involving the N1A/C13A/C8A/N2A/C14A (centroid Cg1), C8A–C13A (centroid Cg2) and N3B/C29B—C33B (centroid Cg3) rings.
For biological activities of benzimidazoles, see: Barreca et al. (2003); Demirayak et al. (2002); Minoura et al. (2004); Pawar et al. (2004); Tomei et al. (2003). For related structures, see: Eltayeb et al. (2007a,b). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL (Sheldrick, 1998); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 1998) and PLATON (Spek, 2003).
C28H28N2O4·C5H5N | Z = 4 |
Mr = 535.62 | F(000) = 1136 |
Triclinic, P1 | Dx = 1.288 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.5355 (1) Å | Cell parameters from 16031 reflections |
b = 17.3405 (3) Å | θ = 1.2–30.0° |
c = 17.8604 (3) Å | µ = 0.09 mm−1 |
α = 92.840 (1)° | T = 100 K |
β = 105.372 (1)° | Block, pale yellow |
γ = 102.523 (1)° | 0.40 × 0.27 × 0.23 mm |
V = 2761.80 (8) Å3 |
Bruker SMART APEXII CCD area-detector diffractometer | 16031 independent reflections |
Radiation source: fine-focus sealed tube | 11052 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
Detector resolution: 8.33 pixels mm-1 | θmax = 30.0°, θmin = 1.2° |
ω scans | h = −13→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −19→24 |
Tmin = 0.967, Tmax = 0.980 | l = −25→25 |
44895 measured reflections |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0668P)2 + 0.0718P] where P = (Fo2 + 2Fc2)/3 |
16031 reflections | (Δ/σ)max = 0.001 |
741 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C28H28N2O4·C5H5N | γ = 102.523 (1)° |
Mr = 535.62 | V = 2761.80 (8) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.5355 (1) Å | Mo Kα radiation |
b = 17.3405 (3) Å | µ = 0.09 mm−1 |
c = 17.8604 (3) Å | T = 100 K |
α = 92.840 (1)° | 0.40 × 0.27 × 0.23 mm |
β = 105.372 (1)° |
Bruker SMART APEXII CCD area-detector diffractometer | 16031 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 11052 reflections with I > 2σ(I) |
Tmin = 0.967, Tmax = 0.980 | Rint = 0.035 |
44895 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.143 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.34 e Å−3 |
16031 reflections | Δρmin = −0.29 e Å−3 |
741 parameters |
Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. |
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. |
x | y | z | Uiso*/Ueq | ||
O1A | 0.69329 (11) | 0.40199 (6) | 0.28400 (6) | 0.0198 (2) | |
H1OA | 0.746 (2) | 0.4550 (12) | 0.2942 (11) | 0.059 (6)* | |
O2A | 0.61443 (10) | 0.51795 (5) | 0.35805 (5) | 0.0193 (2) | |
O3A | 0.42381 (10) | 0.13523 (6) | 0.09510 (5) | 0.0183 (2) | |
H3OA | 0.423 (2) | 0.1324 (11) | 0.0430 (11) | 0.049 (6)* | |
O4A | 0.19547 (11) | 0.14126 (6) | −0.02821 (5) | 0.0218 (2) | |
N1A | 0.37505 (12) | 0.04523 (6) | 0.28948 (6) | 0.0144 (2) | |
N2A | 0.50051 (12) | 0.16685 (6) | 0.27712 (6) | 0.0133 (2) | |
C1A | 0.56764 (14) | 0.38543 (7) | 0.30790 (7) | 0.0142 (3) | |
C2A | 0.52048 (14) | 0.44352 (7) | 0.34607 (7) | 0.0154 (3) | |
C3A | 0.38987 (15) | 0.42383 (8) | 0.36832 (7) | 0.0170 (3) | |
H3A | 0.3594 | 0.4628 | 0.3934 | 0.020* | |
C4A | 0.30335 (15) | 0.34527 (8) | 0.35323 (8) | 0.0175 (3) | |
C5A | 0.35165 (15) | 0.28816 (8) | 0.31613 (7) | 0.0167 (3) | |
H5A | 0.2948 | 0.2360 | 0.3060 | 0.020* | |
C6A | 0.48255 (14) | 0.30686 (7) | 0.29373 (7) | 0.0134 (2) | |
C7A | 0.53506 (15) | 0.24556 (7) | 0.25165 (7) | 0.0147 (3) | |
H7A | 0.4881 | 0.2421 | 0.1959 | 0.018* | |
H7B | 0.6425 | 0.2630 | 0.2605 | 0.018* | |
C8A | 0.58195 (14) | 0.14521 (7) | 0.34609 (7) | 0.0138 (3) | |
C9A | 0.71464 (15) | 0.18474 (8) | 0.40171 (8) | 0.0183 (3) | |
H9A | 0.7651 | 0.2359 | 0.3974 | 0.022* | |
C10A | 0.76712 (15) | 0.14376 (8) | 0.46368 (8) | 0.0203 (3) | |
H10A | 0.8553 | 0.1680 | 0.5020 | 0.024* | |
C11A | 0.69072 (15) | 0.06663 (8) | 0.47024 (8) | 0.0205 (3) | |
H11A | 0.7298 | 0.0408 | 0.5125 | 0.025* | |
C12A | 0.55826 (15) | 0.02824 (8) | 0.41505 (7) | 0.0179 (3) | |
H12A | 0.5078 | −0.0228 | 0.4195 | 0.021* | |
C13A | 0.50319 (14) | 0.06894 (7) | 0.35252 (7) | 0.0148 (3) | |
C14A | 0.37763 (14) | 0.10462 (7) | 0.24591 (7) | 0.0132 (2) | |
C15A | 0.25636 (14) | 0.10407 (7) | 0.17408 (7) | 0.0142 (3) | |
C16A | 0.28195 (14) | 0.12015 (7) | 0.10242 (7) | 0.0151 (3) | |
C17A | 0.15828 (15) | 0.12027 (8) | 0.03814 (7) | 0.0169 (3) | |
C18A | 0.01458 (15) | 0.09840 (8) | 0.04422 (8) | 0.0183 (3) | |
H18A | −0.0658 | 0.0972 | 0.0008 | 0.022* | |
C19A | −0.01247 (14) | 0.07781 (8) | 0.11501 (8) | 0.0168 (3) | |
C20A | 0.10845 (14) | 0.08213 (7) | 0.17913 (7) | 0.0159 (3) | |
H20A | 0.0919 | 0.0703 | 0.2267 | 0.019* | |
C21A | −0.17410 (15) | 0.05094 (8) | 0.11641 (8) | 0.0200 (3) | |
H21A | −0.2180 | 0.0966 | 0.1110 | 0.024* | |
H21B | −0.2277 | 0.0127 | 0.0709 | 0.024* | |
C22A | −0.20089 (15) | 0.01432 (8) | 0.18715 (8) | 0.0201 (3) | |
H22A | −0.1487 | −0.0234 | 0.2061 | 0.024* | |
C23A | −0.29377 (16) | 0.03243 (9) | 0.22407 (8) | 0.0247 (3) | |
H23A | −0.3475 | 0.0700 | 0.2065 | 0.030* | |
H23B | −0.3058 | 0.0077 | 0.2677 | 0.030* | |
C24A | 0.07727 (17) | 0.14857 (9) | −0.09374 (8) | 0.0255 (3) | |
H24A | 0.1181 | 0.1666 | −0.1352 | 0.038* | |
H24B | 0.0264 | 0.1862 | −0.0788 | 0.038* | |
H24C | 0.0078 | 0.0978 | −0.1112 | 0.038* | |
C25A | 0.58045 (18) | 0.57919 (8) | 0.40139 (8) | 0.0248 (3) | |
H25A | 0.6582 | 0.6269 | 0.4093 | 0.037* | |
H25B | 0.5735 | 0.5628 | 0.4511 | 0.037* | |
H25C | 0.4867 | 0.5891 | 0.3729 | 0.037* | |
C26A | 0.15495 (15) | 0.32332 (9) | 0.37223 (8) | 0.0220 (3) | |
H26A | 0.1489 | 0.2751 | 0.3977 | 0.026* | |
H26B | 0.1484 | 0.3655 | 0.4080 | 0.026* | |
C27A | 0.02750 (16) | 0.31078 (9) | 0.29955 (9) | 0.0264 (3) | |
H27A | 0.0083 | 0.3554 | 0.2758 | 0.032* | |
C28A | −0.05956 (17) | 0.24102 (9) | 0.26674 (9) | 0.0303 (4) | |
H28A | −0.0436 | 0.1951 | 0.2889 | 0.036* | |
H28B | −0.1371 | 0.2376 | 0.2214 | 0.036* | |
O1B | 1.19577 (11) | 0.90182 (6) | 0.29353 (6) | 0.0203 (2) | |
H1OB | 1.235 (2) | 0.9548 (13) | 0.2989 (12) | 0.068 (7)* | |
O2B | 1.09294 (10) | 1.01306 (5) | 0.36193 (5) | 0.0193 (2) | |
O3B | 0.96691 (10) | 0.64026 (6) | 0.10956 (5) | 0.0199 (2) | |
H3OB | 0.986 (2) | 0.6472 (12) | 0.0579 (12) | 0.070 (7)* | |
O4B | 0.75469 (11) | 0.64354 (6) | −0.02223 (5) | 0.0232 (2) | |
N1B | 0.88956 (12) | 0.54180 (6) | 0.29220 (6) | 0.0146 (2) | |
N2B | 1.02152 (12) | 0.66375 (6) | 0.28601 (6) | 0.0142 (2) | |
C1B | 1.06728 (14) | 0.88114 (7) | 0.31508 (7) | 0.0147 (3) | |
C2B | 1.00811 (15) | 0.93630 (7) | 0.34968 (7) | 0.0156 (3) | |
C3B | 0.87434 (15) | 0.91182 (8) | 0.36796 (7) | 0.0168 (3) | |
H3B | 0.8367 | 0.9487 | 0.3913 | 0.020* | |
C4B | 0.79479 (14) | 0.83190 (8) | 0.35160 (7) | 0.0162 (3) | |
C5B | 0.85647 (15) | 0.77762 (8) | 0.31965 (7) | 0.0163 (3) | |
H5B | 0.8064 | 0.7242 | 0.3101 | 0.020* | |
C6B | 0.99201 (14) | 0.80129 (7) | 0.30143 (7) | 0.0147 (3) | |
C7B | 1.05948 (15) | 0.74390 (7) | 0.26440 (8) | 0.0166 (3) | |
H7C | 1.0246 | 0.7422 | 0.2080 | 0.020* | |
H7D | 1.1676 | 0.7633 | 0.2801 | 0.020* | |
C8B | 1.09676 (14) | 0.63925 (8) | 0.35443 (7) | 0.0148 (3) | |
C9B | 1.22821 (15) | 0.67600 (8) | 0.41216 (8) | 0.0195 (3) | |
H9B | 1.2819 | 0.7270 | 0.4099 | 0.023* | |
C10B | 1.27469 (16) | 0.63259 (9) | 0.47308 (8) | 0.0227 (3) | |
H10B | 1.3622 | 0.6548 | 0.5126 | 0.027* | |
C11B | 1.19300 (16) | 0.55598 (9) | 0.47661 (8) | 0.0216 (3) | |
H11B | 1.2273 | 0.5286 | 0.5185 | 0.026* | |
C12B | 1.06213 (15) | 0.51991 (8) | 0.41906 (7) | 0.0185 (3) | |
H12B | 1.0086 | 0.4689 | 0.4216 | 0.022* | |
C13B | 1.01378 (14) | 0.56272 (7) | 0.35738 (7) | 0.0147 (3) | |
C14B | 0.89811 (14) | 0.60316 (7) | 0.25106 (7) | 0.0136 (3) | |
C15B | 0.78385 (14) | 0.60625 (7) | 0.17782 (7) | 0.0147 (3) | |
C16B | 0.82149 (14) | 0.62438 (7) | 0.10954 (7) | 0.0154 (3) | |
C17B | 0.70587 (15) | 0.62437 (8) | 0.04144 (7) | 0.0177 (3) | |
C18B | 0.55764 (15) | 0.60432 (8) | 0.04185 (8) | 0.0190 (3) | |
H18B | 0.4825 | 0.6038 | −0.0038 | 0.023* | |
C19B | 0.51918 (15) | 0.58466 (8) | 0.11046 (8) | 0.0179 (3) | |
C20B | 0.63284 (14) | 0.58603 (7) | 0.17762 (7) | 0.0160 (3) | |
H15B | 0.6090 | 0.5733 | 0.2234 | 0.019* | |
C21B | 0.35492 (15) | 0.56373 (9) | 0.10803 (8) | 0.0225 (3) | |
H21C | 0.3162 | 0.6108 | 0.0992 | 0.027* | |
H21D | 0.3009 | 0.5241 | 0.0637 | 0.027* | |
C22B | 0.32253 (15) | 0.53259 (9) | 0.17998 (8) | 0.0237 (3) | |
H22B | 0.3570 | 0.4883 | 0.1966 | 0.028* | |
C23B | 0.24884 (18) | 0.56352 (11) | 0.22121 (9) | 0.0354 (4) | |
H23C | 0.2128 | 0.6078 | 0.2063 | 0.042* | |
H23D | 0.2326 | 0.5412 | 0.2654 | 0.042* | |
C24B | 0.64838 (17) | 0.65859 (9) | −0.08925 (8) | 0.0263 (3) | |
H24D | 0.6974 | 0.6746 | −0.1284 | 0.039* | |
H24E | 0.6054 | 0.7002 | −0.0748 | 0.039* | |
H24F | 0.5707 | 0.6111 | −0.1097 | 0.039* | |
C25B | 1.03920 (16) | 1.07091 (8) | 0.39887 (8) | 0.0224 (3) | |
H25D | 1.1056 | 1.1223 | 0.4037 | 0.034* | |
H25E | 1.0352 | 1.0573 | 0.4498 | 0.034* | |
H25F | 0.9408 | 1.0720 | 0.3679 | 0.034* | |
C26B | 0.64624 (15) | 0.80558 (8) | 0.36944 (8) | 0.0193 (3) | |
H26C | 0.5897 | 0.8457 | 0.3563 | 0.023* | |
H26D | 0.5897 | 0.7567 | 0.3364 | 0.023* | |
C27B | 0.66083 (15) | 0.79207 (8) | 0.45316 (8) | 0.0202 (3) | |
H27B | 0.7281 | 0.7625 | 0.4759 | 0.024* | |
C28B | 0.58663 (17) | 0.81850 (9) | 0.49721 (9) | 0.0271 (3) | |
H28C | 0.5183 | 0.8483 | 0.4768 | 0.033* | |
H28D | 0.6025 | 0.8073 | 0.5488 | 0.033* | |
N3A | 0.92807 (13) | 0.34672 (7) | 0.01349 (7) | 0.0224 (3) | |
C29A | 0.96230 (16) | 0.41376 (9) | 0.06201 (8) | 0.0238 (3) | |
H29A | 1.0380 | 0.4557 | 0.0576 | 0.029* | |
C30A | 0.89068 (16) | 0.42350 (9) | 0.11814 (8) | 0.0248 (3) | |
H30A | 0.9178 | 0.4709 | 0.1509 | 0.030* | |
C31A | 0.77808 (16) | 0.36174 (9) | 0.12486 (8) | 0.0255 (3) | |
H31A | 0.7272 | 0.3668 | 0.1619 | 0.031* | |
C32A | 0.74217 (16) | 0.29227 (9) | 0.07563 (8) | 0.0251 (3) | |
H32A | 0.6672 | 0.2495 | 0.0792 | 0.030* | |
C33A | 0.81932 (16) | 0.28732 (9) | 0.02099 (8) | 0.0233 (3) | |
H33A | 0.7943 | 0.2403 | −0.0122 | 0.028* | |
N3B | 0.49267 (13) | 0.13148 (7) | 0.95301 (6) | 0.0205 (3) | |
C29B | 0.57110 (15) | 0.08262 (8) | 0.93302 (8) | 0.0215 (3) | |
H29B | 0.5889 | 0.0420 | 0.9636 | 0.026* | |
C30B | 0.62726 (16) | 0.08964 (9) | 0.86879 (8) | 0.0239 (3) | |
H30B | 0.6816 | 0.0546 | 0.8570 | 0.029* | |
C31B | 0.60102 (16) | 0.14943 (9) | 0.82286 (8) | 0.0260 (3) | |
H31B | 0.6380 | 0.1557 | 0.7797 | 0.031* | |
C32B | 0.51883 (17) | 0.19984 (9) | 0.84209 (8) | 0.0259 (3) | |
H32B | 0.4986 | 0.2404 | 0.8119 | 0.031* | |
C33B | 0.46716 (16) | 0.18877 (8) | 0.90711 (8) | 0.0222 (3) | |
H33B | 0.4118 | 0.2229 | 0.9197 | 0.027* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0206 (5) | 0.0133 (5) | 0.0267 (5) | −0.0003 (4) | 0.0126 (4) | −0.0001 (4) |
O2A | 0.0236 (5) | 0.0117 (5) | 0.0224 (5) | 0.0019 (4) | 0.0085 (4) | −0.0017 (4) |
O3A | 0.0159 (5) | 0.0238 (5) | 0.0162 (5) | 0.0035 (4) | 0.0072 (4) | 0.0022 (4) |
O4A | 0.0209 (5) | 0.0316 (6) | 0.0138 (4) | 0.0071 (4) | 0.0052 (4) | 0.0070 (4) |
N1A | 0.0151 (6) | 0.0130 (5) | 0.0151 (5) | 0.0028 (4) | 0.0048 (4) | 0.0020 (4) |
N2A | 0.0133 (5) | 0.0114 (5) | 0.0148 (5) | 0.0017 (4) | 0.0042 (4) | 0.0012 (4) |
C1A | 0.0152 (6) | 0.0146 (6) | 0.0133 (6) | 0.0041 (5) | 0.0039 (5) | 0.0034 (5) |
C2A | 0.0184 (7) | 0.0122 (6) | 0.0138 (6) | 0.0027 (5) | 0.0027 (5) | 0.0009 (5) |
C3A | 0.0213 (7) | 0.0157 (7) | 0.0158 (6) | 0.0079 (5) | 0.0056 (5) | 0.0009 (5) |
C4A | 0.0175 (7) | 0.0186 (7) | 0.0177 (6) | 0.0057 (5) | 0.0061 (5) | 0.0026 (5) |
C5A | 0.0171 (7) | 0.0137 (6) | 0.0189 (6) | 0.0027 (5) | 0.0051 (5) | 0.0029 (5) |
C6A | 0.0145 (6) | 0.0138 (6) | 0.0117 (6) | 0.0041 (5) | 0.0027 (5) | 0.0015 (5) |
C7A | 0.0175 (7) | 0.0108 (6) | 0.0169 (6) | 0.0024 (5) | 0.0072 (5) | 0.0027 (5) |
C8A | 0.0141 (6) | 0.0158 (6) | 0.0132 (6) | 0.0046 (5) | 0.0059 (5) | 0.0026 (5) |
C9A | 0.0166 (7) | 0.0177 (7) | 0.0194 (6) | 0.0019 (5) | 0.0059 (5) | −0.0019 (5) |
C10A | 0.0148 (7) | 0.0279 (8) | 0.0165 (6) | 0.0060 (5) | 0.0015 (5) | −0.0015 (6) |
C11A | 0.0223 (7) | 0.0267 (8) | 0.0159 (6) | 0.0121 (6) | 0.0054 (6) | 0.0058 (6) |
C12A | 0.0206 (7) | 0.0188 (7) | 0.0171 (6) | 0.0070 (5) | 0.0077 (6) | 0.0054 (5) |
C13A | 0.0156 (7) | 0.0153 (6) | 0.0149 (6) | 0.0043 (5) | 0.0066 (5) | −0.0005 (5) |
C14A | 0.0133 (6) | 0.0121 (6) | 0.0150 (6) | 0.0026 (5) | 0.0060 (5) | 0.0000 (5) |
C15A | 0.0148 (6) | 0.0124 (6) | 0.0146 (6) | 0.0032 (5) | 0.0030 (5) | 0.0019 (5) |
C16A | 0.0152 (7) | 0.0140 (6) | 0.0164 (6) | 0.0032 (5) | 0.0052 (5) | 0.0020 (5) |
C17A | 0.0202 (7) | 0.0174 (7) | 0.0138 (6) | 0.0058 (5) | 0.0049 (5) | 0.0029 (5) |
C18A | 0.0167 (7) | 0.0223 (7) | 0.0151 (6) | 0.0054 (5) | 0.0026 (5) | 0.0030 (5) |
C19A | 0.0148 (7) | 0.0179 (7) | 0.0175 (6) | 0.0050 (5) | 0.0034 (5) | 0.0020 (5) |
C20A | 0.0177 (7) | 0.0156 (6) | 0.0147 (6) | 0.0042 (5) | 0.0052 (5) | 0.0021 (5) |
C21A | 0.0144 (7) | 0.0253 (8) | 0.0192 (7) | 0.0044 (5) | 0.0035 (5) | 0.0012 (6) |
C22A | 0.0148 (7) | 0.0231 (7) | 0.0199 (7) | 0.0025 (5) | 0.0024 (5) | 0.0013 (6) |
C23A | 0.0203 (8) | 0.0319 (8) | 0.0213 (7) | 0.0042 (6) | 0.0065 (6) | 0.0016 (6) |
C24A | 0.0269 (8) | 0.0359 (9) | 0.0157 (6) | 0.0121 (6) | 0.0047 (6) | 0.0086 (6) |
C25A | 0.0363 (9) | 0.0145 (7) | 0.0240 (7) | 0.0068 (6) | 0.0093 (7) | −0.0020 (6) |
C26A | 0.0210 (7) | 0.0219 (7) | 0.0273 (7) | 0.0063 (5) | 0.0127 (6) | 0.0030 (6) |
C27A | 0.0203 (8) | 0.0278 (8) | 0.0370 (8) | 0.0111 (6) | 0.0120 (7) | 0.0142 (7) |
C28A | 0.0236 (8) | 0.0332 (9) | 0.0347 (9) | 0.0090 (6) | 0.0065 (7) | 0.0088 (7) |
O1B | 0.0199 (5) | 0.0129 (5) | 0.0303 (5) | 0.0007 (4) | 0.0132 (4) | 0.0021 (4) |
O2B | 0.0225 (5) | 0.0115 (5) | 0.0241 (5) | 0.0028 (4) | 0.0084 (4) | −0.0013 (4) |
O3B | 0.0178 (5) | 0.0268 (5) | 0.0167 (5) | 0.0053 (4) | 0.0074 (4) | 0.0031 (4) |
O4B | 0.0240 (6) | 0.0339 (6) | 0.0149 (5) | 0.0106 (4) | 0.0067 (4) | 0.0084 (4) |
N1B | 0.0154 (6) | 0.0145 (5) | 0.0134 (5) | 0.0028 (4) | 0.0038 (4) | 0.0012 (4) |
N2B | 0.0153 (6) | 0.0113 (5) | 0.0154 (5) | 0.0024 (4) | 0.0044 (4) | 0.0008 (4) |
C1B | 0.0153 (6) | 0.0148 (6) | 0.0141 (6) | 0.0033 (5) | 0.0044 (5) | 0.0018 (5) |
C2B | 0.0185 (7) | 0.0128 (6) | 0.0139 (6) | 0.0029 (5) | 0.0027 (5) | 0.0013 (5) |
C3B | 0.0204 (7) | 0.0173 (7) | 0.0141 (6) | 0.0072 (5) | 0.0051 (5) | 0.0010 (5) |
C4B | 0.0156 (7) | 0.0187 (7) | 0.0144 (6) | 0.0041 (5) | 0.0041 (5) | 0.0024 (5) |
C5B | 0.0180 (7) | 0.0127 (6) | 0.0171 (6) | 0.0008 (5) | 0.0054 (5) | 0.0018 (5) |
C6B | 0.0164 (7) | 0.0138 (6) | 0.0137 (6) | 0.0034 (5) | 0.0043 (5) | 0.0011 (5) |
C7B | 0.0190 (7) | 0.0119 (6) | 0.0202 (6) | 0.0025 (5) | 0.0084 (5) | 0.0035 (5) |
C8B | 0.0156 (7) | 0.0156 (6) | 0.0143 (6) | 0.0036 (5) | 0.0062 (5) | 0.0006 (5) |
C9B | 0.0178 (7) | 0.0191 (7) | 0.0195 (7) | 0.0014 (5) | 0.0049 (6) | −0.0020 (5) |
C10B | 0.0183 (7) | 0.0289 (8) | 0.0173 (7) | 0.0046 (6) | 0.0007 (6) | −0.0031 (6) |
C11B | 0.0233 (8) | 0.0279 (8) | 0.0160 (6) | 0.0117 (6) | 0.0044 (6) | 0.0054 (6) |
C12B | 0.0216 (7) | 0.0190 (7) | 0.0171 (6) | 0.0065 (5) | 0.0073 (6) | 0.0055 (5) |
C13B | 0.0148 (6) | 0.0154 (6) | 0.0147 (6) | 0.0040 (5) | 0.0056 (5) | 0.0000 (5) |
C14B | 0.0143 (6) | 0.0119 (6) | 0.0152 (6) | 0.0028 (5) | 0.0059 (5) | 0.0002 (5) |
C15B | 0.0160 (7) | 0.0118 (6) | 0.0156 (6) | 0.0035 (5) | 0.0034 (5) | 0.0004 (5) |
C16B | 0.0160 (7) | 0.0147 (6) | 0.0166 (6) | 0.0047 (5) | 0.0056 (5) | 0.0019 (5) |
C17B | 0.0224 (7) | 0.0184 (7) | 0.0139 (6) | 0.0073 (5) | 0.0053 (5) | 0.0035 (5) |
C18B | 0.0181 (7) | 0.0211 (7) | 0.0169 (6) | 0.0070 (5) | 0.0017 (5) | 0.0025 (5) |
C19B | 0.0175 (7) | 0.0171 (7) | 0.0185 (6) | 0.0052 (5) | 0.0034 (5) | 0.0013 (5) |
C20B | 0.0177 (7) | 0.0149 (6) | 0.0163 (6) | 0.0038 (5) | 0.0061 (5) | 0.0026 (5) |
C21B | 0.0160 (7) | 0.0277 (8) | 0.0218 (7) | 0.0054 (5) | 0.0021 (6) | 0.0017 (6) |
C22B | 0.0156 (7) | 0.0303 (8) | 0.0238 (7) | 0.0049 (6) | 0.0039 (6) | 0.0017 (6) |
C23B | 0.0277 (9) | 0.0536 (11) | 0.0290 (8) | 0.0180 (8) | 0.0086 (7) | 0.0032 (8) |
C24B | 0.0300 (9) | 0.0364 (9) | 0.0156 (7) | 0.0147 (7) | 0.0055 (6) | 0.0087 (6) |
C25B | 0.0290 (8) | 0.0160 (7) | 0.0219 (7) | 0.0073 (6) | 0.0058 (6) | −0.0027 (6) |
C26B | 0.0158 (7) | 0.0228 (7) | 0.0186 (6) | 0.0031 (5) | 0.0051 (5) | 0.0009 (5) |
C27B | 0.0199 (7) | 0.0184 (7) | 0.0218 (7) | 0.0031 (5) | 0.0064 (6) | 0.0020 (6) |
C28B | 0.0276 (8) | 0.0297 (8) | 0.0247 (7) | 0.0035 (6) | 0.0111 (7) | 0.0023 (6) |
N3A | 0.0174 (6) | 0.0311 (7) | 0.0174 (6) | 0.0037 (5) | 0.0048 (5) | 0.0013 (5) |
C29A | 0.0217 (8) | 0.0229 (8) | 0.0230 (7) | −0.0008 (6) | 0.0050 (6) | 0.0029 (6) |
C30A | 0.0249 (8) | 0.0237 (8) | 0.0230 (7) | 0.0071 (6) | 0.0024 (6) | −0.0040 (6) |
C31A | 0.0216 (8) | 0.0393 (9) | 0.0178 (7) | 0.0092 (6) | 0.0079 (6) | 0.0012 (6) |
C32A | 0.0197 (8) | 0.0282 (8) | 0.0245 (7) | −0.0016 (6) | 0.0072 (6) | 0.0036 (6) |
C33A | 0.0205 (7) | 0.0248 (8) | 0.0212 (7) | 0.0026 (6) | 0.0034 (6) | −0.0015 (6) |
N3B | 0.0172 (6) | 0.0249 (7) | 0.0176 (6) | 0.0021 (5) | 0.0045 (5) | 0.0004 (5) |
C29B | 0.0168 (7) | 0.0219 (7) | 0.0213 (7) | 0.0016 (5) | 0.0006 (6) | 0.0012 (6) |
C30B | 0.0179 (7) | 0.0259 (8) | 0.0254 (7) | 0.0043 (6) | 0.0046 (6) | −0.0074 (6) |
C31B | 0.0227 (8) | 0.0351 (9) | 0.0180 (7) | −0.0005 (6) | 0.0086 (6) | −0.0017 (6) |
C32B | 0.0252 (8) | 0.0288 (8) | 0.0228 (7) | 0.0048 (6) | 0.0059 (6) | 0.0065 (6) |
C33B | 0.0219 (7) | 0.0228 (7) | 0.0226 (7) | 0.0058 (6) | 0.0072 (6) | 0.0009 (6) |
O1A—C1A | 1.3544 (15) | N2B—C8B | 1.3811 (16) |
O1A—H1OA | 0.93 (2) | N2B—C7B | 1.4562 (15) |
O2A—C2A | 1.3724 (15) | C1B—C6B | 1.3909 (17) |
O2A—C25A | 1.4258 (16) | C1B—C2B | 1.4055 (18) |
O3A—C16A | 1.3635 (15) | C2B—C3B | 1.3833 (18) |
O3A—H3OA | 0.929 (19) | C3B—C4B | 1.4029 (18) |
O4A—C17A | 1.3684 (15) | C3B—H3B | 0.93 |
O4A—C24A | 1.4260 (16) | C4B—C5B | 1.3864 (18) |
N1A—C14A | 1.3211 (16) | C4B—C26B | 1.5132 (18) |
N1A—C13A | 1.3917 (16) | C5B—C6B | 1.3968 (17) |
N2A—C14A | 1.3761 (15) | C5B—H5B | 0.93 |
N2A—C8A | 1.3878 (16) | C6B—C7B | 1.5099 (18) |
N2A—C7A | 1.4575 (15) | C7B—H7C | 0.97 |
C1A—C6A | 1.3987 (17) | C7B—H7D | 0.97 |
C1A—C2A | 1.4044 (18) | C8B—C9B | 1.3942 (18) |
C2A—C3A | 1.3845 (18) | C8B—C13B | 1.4013 (17) |
C3A—C4A | 1.4026 (18) | C9B—C10B | 1.3846 (19) |
C3A—H3A | 0.93 | C9B—H9B | 0.93 |
C4A—C5A | 1.3880 (18) | C10B—C11B | 1.400 (2) |
C4A—C26A | 1.5153 (18) | C10B—H10B | 0.93 |
C5A—C6A | 1.3875 (17) | C11B—C12B | 1.3866 (19) |
C5A—H5A | 0.93 | C11B—H11B | 0.93 |
C6A—C7A | 1.5156 (17) | C12B—C13B | 1.3919 (18) |
C7A—H7A | 0.97 | C12B—H12B | 0.93 |
C7A—H7B | 0.97 | C14B—C15B | 1.4757 (17) |
C8A—C9A | 1.3956 (18) | C15B—C16B | 1.3914 (17) |
C8A—C13A | 1.3988 (17) | C15B—C20B | 1.4052 (18) |
C9A—C10A | 1.3854 (19) | C16B—C17B | 1.4085 (18) |
C9A—H9A | 0.93 | C17B—C18B | 1.3826 (19) |
C10A—C11A | 1.4040 (19) | C18B—C19B | 1.4062 (18) |
C10A—H10A | 0.93 | C18B—H18B | 0.93 |
C11A—C12A | 1.3857 (19) | C19B—C20B | 1.3823 (18) |
C11A—H11A | 0.93 | C19B—C21B | 1.5175 (19) |
C12A—C13A | 1.3961 (18) | C20B—H15B | 0.93 |
C12A—H12A | 0.93 | C21B—C22B | 1.4983 (19) |
C14A—C15A | 1.4802 (17) | C21B—H21C | 0.97 |
C15A—C16A | 1.3952 (17) | C21B—H21D | 0.97 |
C15A—C20A | 1.4072 (18) | C22B—C23B | 1.312 (2) |
C16A—C17A | 1.4114 (18) | C22B—H22B | 0.93 |
C17A—C18A | 1.3750 (18) | C23B—H23C | 0.93 |
C18A—C19A | 1.4037 (18) | C23B—H23D | 0.93 |
C18A—H18A | 0.93 | C24B—H24D | 0.96 |
C19A—C20A | 1.3785 (18) | C24B—H24E | 0.96 |
C19A—C21A | 1.5176 (18) | C24B—H24F | 0.96 |
C20A—H20A | 0.93 | C25B—H25D | 0.96 |
C21A—C22A | 1.4984 (18) | C25B—H25E | 0.96 |
C21A—H21A | 0.97 | C25B—H25F | 0.96 |
C21A—H21B | 0.97 | C26B—C27B | 1.4996 (18) |
C22A—C23A | 1.3143 (19) | C26B—H26C | 0.97 |
C22A—H22A | 0.93 | C26B—H26D | 0.97 |
C23A—H23A | 0.93 | C27B—C28B | 1.3151 (19) |
C23A—H23B | 0.93 | C27B—H27B | 0.93 |
C24A—H24A | 0.96 | C28B—H28C | 0.93 |
C24A—H24B | 0.96 | C28B—H28D | 0.93 |
C24A—H24C | 0.96 | N3A—C33A | 1.3336 (17) |
C25A—H25A | 0.96 | N3A—C29A | 1.3397 (18) |
C25A—H25B | 0.96 | C29A—C30A | 1.377 (2) |
C25A—H25C | 0.96 | C29A—H29A | 0.93 |
C26A—C27A | 1.493 (2) | C30A—C31A | 1.377 (2) |
C26A—H26A | 0.97 | C30A—H30A | 0.93 |
C26A—H26B | 0.97 | C31A—C32A | 1.378 (2) |
C27A—C28A | 1.316 (2) | C31A—H31A | 0.93 |
C27A—H27A | 0.93 | C32A—C33A | 1.3786 (19) |
C28A—H28A | 0.93 | C32A—H32A | 0.93 |
C28A—H28B | 0.93 | C33A—H33A | 0.93 |
O1B—C1B | 1.3606 (15) | N3B—C29B | 1.3383 (18) |
O1B—H1OB | 0.90 (2) | N3B—C33B | 1.3408 (18) |
O2B—C2B | 1.3727 (15) | C29B—C30B | 1.389 (2) |
O2B—C25B | 1.4285 (16) | C29B—H29B | 0.93 |
O3B—C16B | 1.3538 (15) | C30B—C31B | 1.378 (2) |
O3B—H3OB | 0.99 (2) | C30B—H30B | 0.93 |
O4B—C17B | 1.3679 (15) | C31B—C32B | 1.381 (2) |
O4B—C24B | 1.4252 (16) | C31B—H31B | 0.93 |
N1B—C14B | 1.3229 (16) | C32B—C33B | 1.3830 (19) |
N1B—C13B | 1.3895 (16) | C32B—H32B | 0.93 |
N2B—C14B | 1.3740 (15) | C33B—H33B | 0.93 |
C1A—O1A—H1OA | 114.9 (12) | C4B—C3B—H3B | 119.7 |
C2A—O2A—C25A | 117.52 (10) | C5B—C4B—C3B | 118.40 (12) |
C16A—O3A—H3OA | 111.5 (12) | C5B—C4B—C26B | 120.93 (12) |
C17A—O4A—C24A | 117.37 (10) | C3B—C4B—C26B | 120.67 (12) |
C14A—N1A—C13A | 105.60 (10) | C4B—C5B—C6B | 121.56 (12) |
C14A—N2A—C8A | 106.81 (10) | C4B—C5B—H5B | 119.2 |
C14A—N2A—C7A | 128.94 (11) | C6B—C5B—H5B | 119.2 |
C8A—N2A—C7A | 123.80 (10) | C1B—C6B—C5B | 119.63 (12) |
O1A—C1A—C6A | 117.93 (11) | C1B—C6B—C7B | 117.63 (11) |
O1A—C1A—C2A | 122.79 (11) | C5B—C6B—C7B | 122.70 (11) |
C6A—C1A—C2A | 119.28 (12) | N2B—C7B—C6B | 112.87 (10) |
O2A—C2A—C3A | 125.45 (12) | N2B—C7B—H7C | 109.0 |
O2A—C2A—C1A | 113.95 (11) | C6B—C7B—H7C | 109.0 |
C3A—C2A—C1A | 120.60 (12) | N2B—C7B—H7D | 109.0 |
C2A—C3A—C4A | 120.20 (12) | C6B—C7B—H7D | 109.0 |
C2A—C3A—H3A | 119.9 | H7C—C7B—H7D | 107.8 |
C4A—C3A—H3A | 119.9 | N2B—C8B—C9B | 131.90 (12) |
C5A—C4A—C3A | 118.76 (12) | N2B—C8B—C13B | 105.64 (11) |
C5A—C4A—C26A | 119.99 (12) | C9B—C8B—C13B | 122.45 (12) |
C3A—C4A—C26A | 121.15 (12) | C10B—C9B—C8B | 116.54 (13) |
C6A—C5A—C4A | 121.75 (12) | C10B—C9B—H9B | 121.7 |
C6A—C5A—H5A | 119.1 | C8B—C9B—H9B | 121.7 |
C4A—C5A—H5A | 119.1 | C9B—C10B—C11B | 121.57 (13) |
C5A—C6A—C1A | 119.40 (12) | C9B—C10B—H10B | 119.2 |
C5A—C6A—C7A | 122.38 (11) | C11B—C10B—H10B | 119.2 |
C1A—C6A—C7A | 118.18 (11) | C12B—C11B—C10B | 121.54 (13) |
N2A—C7A—C6A | 113.00 (10) | C12B—C11B—H11B | 119.2 |
N2A—C7A—H7A | 109.0 | C10B—C11B—H11B | 119.2 |
C6A—C7A—H7A | 109.0 | C11B—C12B—C13B | 117.64 (12) |
N2A—C7A—H7B | 109.0 | C11B—C12B—H12B | 121.2 |
C6A—C7A—H7B | 109.0 | C13B—C12B—H12B | 121.2 |
H7A—C7A—H7B | 107.8 | N1B—C13B—C12B | 130.21 (12) |
N2A—C8A—C9A | 131.98 (12) | N1B—C13B—C8B | 109.53 (11) |
N2A—C8A—C13A | 105.56 (11) | C12B—C13B—C8B | 120.25 (12) |
C9A—C8A—C13A | 122.46 (12) | N1B—C14B—N2B | 112.18 (11) |
C10A—C9A—C8A | 116.43 (12) | N1B—C14B—C15B | 123.12 (11) |
C10A—C9A—H9A | 121.8 | N2B—C14B—C15B | 124.66 (11) |
C8A—C9A—H9A | 121.8 | C16B—C15B—C20B | 120.20 (12) |
C9A—C10A—C11A | 121.77 (13) | C16B—C15B—C14B | 121.96 (11) |
C9A—C10A—H10A | 119.1 | C20B—C15B—C14B | 117.76 (11) |
C11A—C10A—H10A | 119.1 | O3B—C16B—C15B | 119.68 (11) |
C12A—C11A—C10A | 121.31 (12) | O3B—C16B—C17B | 121.62 (11) |
C12A—C11A—H11A | 119.3 | C15B—C16B—C17B | 118.70 (12) |
C10A—C11A—H11A | 119.3 | O4B—C17B—C18B | 125.26 (12) |
C11A—C12A—C13A | 117.66 (12) | O4B—C17B—C16B | 114.11 (11) |
C11A—C12A—H12A | 121.2 | C18B—C17B—C16B | 120.61 (12) |
C13A—C12A—H12A | 121.2 | C17B—C18B—C19B | 120.78 (12) |
N1A—C13A—C12A | 129.94 (12) | C17B—C18B—H18B | 119.6 |
N1A—C13A—C8A | 109.70 (11) | C19B—C18B—H18B | 119.6 |
C12A—C13A—C8A | 120.35 (12) | C20B—C19B—C18B | 118.57 (12) |
N1A—C14A—N2A | 112.31 (11) | C20B—C19B—C21B | 122.68 (12) |
N1A—C14A—C15A | 122.58 (11) | C18B—C19B—C21B | 118.75 (12) |
N2A—C14A—C15A | 125.03 (11) | C19B—C20B—C15B | 121.11 (12) |
C16A—C15A—C20A | 119.61 (12) | C19B—C20B—H15B | 119.4 |
C16A—C15A—C14A | 123.35 (11) | C15B—C20B—H15B | 119.4 |
C20A—C15A—C14A | 116.96 (11) | C22B—C21B—C19B | 115.21 (11) |
O3A—C16A—C15A | 120.33 (11) | C22B—C21B—H21C | 108.5 |
O3A—C16A—C17A | 121.05 (11) | C19B—C21B—H21C | 108.5 |
C15A—C16A—C17A | 118.62 (12) | C22B—C21B—H21D | 108.5 |
O4A—C17A—C18A | 125.04 (12) | C19B—C21B—H21D | 108.5 |
O4A—C17A—C16A | 114.28 (11) | H21C—C21B—H21D | 107.5 |
C18A—C17A—C16A | 120.65 (12) | C23B—C22B—C21B | 124.46 (15) |
C17A—C18A—C19A | 120.90 (12) | C23B—C22B—H22B | 117.8 |
C17A—C18A—H18A | 119.6 | C21B—C22B—H22B | 117.8 |
C19A—C18A—H18A | 119.6 | C22B—C23B—H23C | 120.0 |
C20A—C19A—C18A | 118.54 (12) | C22B—C23B—H23D | 120.0 |
C20A—C19A—C21A | 123.52 (12) | H23C—C23B—H23D | 120.0 |
C18A—C19A—C21A | 117.93 (11) | O4B—C24B—H24D | 109.5 |
C19A—C20A—C15A | 121.43 (12) | O4B—C24B—H24E | 109.5 |
C19A—C20A—H20A | 119.3 | H24D—C24B—H24E | 109.5 |
C15A—C20A—H20A | 119.3 | O4B—C24B—H24F | 109.5 |
C22A—C21A—C19A | 116.96 (11) | H24D—C24B—H24F | 109.5 |
C22A—C21A—H21A | 108.1 | H24E—C24B—H24F | 109.5 |
C19A—C21A—H21A | 108.1 | O2B—C25B—H25D | 109.5 |
C22A—C21A—H21B | 108.1 | O2B—C25B—H25E | 109.5 |
C19A—C21A—H21B | 108.1 | H25D—C25B—H25E | 109.5 |
H21A—C21A—H21B | 107.3 | O2B—C25B—H25F | 109.5 |
C23A—C22A—C21A | 123.88 (14) | H25D—C25B—H25F | 109.5 |
C23A—C22A—H22A | 118.1 | H25E—C25B—H25F | 109.5 |
C21A—C22A—H22A | 118.1 | C27B—C26B—C4B | 113.79 (11) |
C22A—C23A—H23A | 120.0 | C27B—C26B—H26C | 108.8 |
C22A—C23A—H23B | 120.0 | C4B—C26B—H26C | 108.8 |
H23A—C23A—H23B | 120.0 | C27B—C26B—H26D | 108.8 |
O4A—C24A—H24A | 109.5 | C4B—C26B—H26D | 108.8 |
O4A—C24A—H24B | 109.5 | H26C—C26B—H26D | 107.7 |
H24A—C24A—H24B | 109.5 | C28B—C27B—C26B | 125.58 (14) |
O4A—C24A—H24C | 109.5 | C28B—C27B—H27B | 117.2 |
H24A—C24A—H24C | 109.5 | C26B—C27B—H27B | 117.2 |
H24B—C24A—H24C | 109.5 | C27B—C28B—H28C | 120.0 |
O2A—C25A—H25A | 109.5 | C27B—C28B—H28D | 120.0 |
O2A—C25A—H25B | 109.5 | H28C—C28B—H28D | 120.0 |
H25A—C25A—H25B | 109.5 | C33A—N3A—C29A | 117.41 (12) |
O2A—C25A—H25C | 109.5 | N3A—C29A—C30A | 123.10 (13) |
H25A—C25A—H25C | 109.5 | N3A—C29A—H29A | 118.4 |
H25B—C25A—H25C | 109.5 | C30A—C29A—H29A | 118.4 |
C27A—C26A—C4A | 110.61 (11) | C29A—C30A—C31A | 118.78 (13) |
C27A—C26A—H26A | 109.5 | C29A—C30A—H30A | 120.6 |
C4A—C26A—H26A | 109.5 | C31A—C30A—H30A | 120.6 |
C27A—C26A—H26B | 109.5 | C30A—C31A—C32A | 118.77 (13) |
C4A—C26A—H26B | 109.5 | C30A—C31A—H31A | 120.6 |
H26A—C26A—H26B | 108.1 | C32A—C31A—H31A | 120.6 |
C28A—C27A—C26A | 124.60 (14) | C31A—C32A—C33A | 118.84 (13) |
C28A—C27A—H27A | 117.7 | C31A—C32A—H32A | 120.6 |
C26A—C27A—H27A | 117.7 | C33A—C32A—H32A | 120.6 |
C27A—C28A—H28A | 120.0 | N3A—C33A—C32A | 123.10 (13) |
C27A—C28A—H28B | 120.0 | N3A—C33A—H33A | 118.5 |
H28A—C28A—H28B | 120.0 | C32A—C33A—H33A | 118.5 |
C1B—O1B—H1OB | 114.2 (14) | C29B—N3B—C33B | 116.99 (12) |
C2B—O2B—C25B | 116.37 (10) | N3B—C29B—C30B | 123.19 (14) |
C16B—O3B—H3OB | 115.7 (12) | N3B—C29B—H29B | 118.4 |
C17B—O4B—C24B | 117.47 (11) | C30B—C29B—H29B | 118.4 |
C14B—N1B—C13B | 105.63 (10) | C31B—C30B—C29B | 118.87 (14) |
C14B—N2B—C8B | 107.01 (10) | C31B—C30B—H30B | 120.6 |
C14B—N2B—C7B | 128.51 (11) | C29B—C30B—H30B | 120.6 |
C8B—N2B—C7B | 123.89 (10) | C30B—C31B—C32B | 118.73 (13) |
O1B—C1B—C6B | 117.52 (11) | C30B—C31B—H31B | 120.6 |
O1B—C1B—C2B | 123.21 (11) | C32B—C31B—H31B | 120.6 |
C6B—C1B—C2B | 119.26 (12) | C31B—C32B—C33B | 118.71 (14) |
O2B—C2B—C3B | 125.24 (12) | C31B—C32B—H32B | 120.6 |
O2B—C2B—C1B | 114.37 (11) | C33B—C32B—H32B | 120.6 |
C3B—C2B—C1B | 120.38 (12) | N3B—C33B—C32B | 123.51 (14) |
C2B—C3B—C4B | 120.69 (12) | N3B—C33B—H33B | 118.2 |
C2B—C3B—H3B | 119.7 | C32B—C33B—H33B | 118.2 |
C25A—O2A—C2A—C3A | 4.29 (18) | O2B—C2B—C3B—C4B | 178.77 (12) |
C25A—O2A—C2A—C1A | −175.63 (11) | C1B—C2B—C3B—C4B | −0.66 (19) |
O1A—C1A—C2A—O2A | −1.06 (17) | C2B—C3B—C4B—C5B | 2.58 (19) |
C6A—C1A—C2A—O2A | 178.78 (11) | C2B—C3B—C4B—C26B | −178.20 (12) |
O1A—C1A—C2A—C3A | 179.02 (12) | C3B—C4B—C5B—C6B | −2.08 (19) |
C6A—C1A—C2A—C3A | −1.14 (19) | C26B—C4B—C5B—C6B | 178.70 (12) |
O2A—C2A—C3A—C4A | −179.61 (12) | O1B—C1B—C6B—C5B | −177.44 (11) |
C1A—C2A—C3A—C4A | 0.30 (19) | C2B—C1B—C6B—C5B | 2.29 (19) |
C2A—C3A—C4A—C5A | 0.31 (19) | O1B—C1B—C6B—C7B | 0.45 (17) |
C2A—C3A—C4A—C26A | −175.97 (12) | C2B—C1B—C6B—C7B | −179.81 (11) |
C3A—C4A—C5A—C6A | −0.06 (19) | C4B—C5B—C6B—C1B | −0.35 (19) |
C26A—C4A—C5A—C6A | 176.26 (12) | C4B—C5B—C6B—C7B | −178.13 (12) |
C4A—C5A—C6A—C1A | −0.78 (19) | C14B—N2B—C7B—C6B | 87.21 (15) |
C4A—C5A—C6A—C7A | −178.67 (12) | C8B—N2B—C7B—C6B | −82.87 (15) |
O1A—C1A—C6A—C5A | −178.78 (11) | C1B—C6B—C7B—N2B | 151.99 (11) |
C2A—C1A—C6A—C5A | 1.37 (18) | C5B—C6B—C7B—N2B | −30.18 (17) |
O1A—C1A—C6A—C7A | −0.81 (17) | C14B—N2B—C8B—C9B | 179.48 (14) |
C2A—C1A—C6A—C7A | 179.34 (11) | C7B—N2B—C8B—C9B | −8.6 (2) |
C14A—N2A—C7A—C6A | 93.27 (15) | C14B—N2B—C8B—C13B | 0.48 (13) |
C8A—N2A—C7A—C6A | −78.04 (15) | C7B—N2B—C8B—C13B | 172.37 (11) |
C5A—C6A—C7A—N2A | −35.08 (17) | N2B—C8B—C9B—C10B | −178.23 (13) |
C1A—C6A—C7A—N2A | 147.02 (11) | C13B—C8B—C9B—C10B | 0.6 (2) |
C14A—N2A—C8A—C9A | −179.57 (14) | C8B—C9B—C10B—C11B | −0.4 (2) |
C7A—N2A—C8A—C9A | −6.6 (2) | C9B—C10B—C11B—C12B | 0.3 (2) |
C14A—N2A—C8A—C13A | 0.75 (13) | C10B—C11B—C12B—C13B | −0.3 (2) |
C7A—N2A—C8A—C13A | 173.69 (11) | C14B—N1B—C13B—C12B | −178.45 (13) |
N2A—C8A—C9A—C10A | −178.39 (13) | C14B—N1B—C13B—C8B | 0.57 (14) |
C13A—C8A—C9A—C10A | 1.25 (19) | C11B—C12B—C13B—N1B | 179.37 (13) |
C8A—C9A—C10A—C11A | −0.1 (2) | C11B—C12B—C13B—C8B | 0.44 (19) |
C9A—C10A—C11A—C12A | −0.5 (2) | N2B—C8B—C13B—N1B | −0.66 (14) |
C10A—C11A—C12A—C13A | 0.0 (2) | C9B—C8B—C13B—N1B | −179.78 (12) |
C14A—N1A—C13A—C12A | −177.93 (13) | N2B—C8B—C13B—C12B | 178.48 (11) |
C14A—N1A—C13A—C8A | 0.91 (14) | C9B—C8B—C13B—C12B | −0.6 (2) |
C11A—C12A—C13A—N1A | 179.82 (13) | C13B—N1B—C14B—N2B | −0.27 (14) |
C11A—C12A—C13A—C8A | 1.09 (19) | C13B—N1B—C14B—C15B | −177.99 (11) |
N2A—C8A—C13A—N1A | −1.03 (14) | C8B—N2B—C14B—N1B | −0.14 (14) |
C9A—C8A—C13A—N1A | 179.24 (12) | C7B—N2B—C14B—N1B | −171.53 (11) |
N2A—C8A—C13A—C12A | 177.93 (11) | C8B—N2B—C14B—C15B | 177.54 (11) |
C9A—C8A—C13A—C12A | −1.79 (19) | C7B—N2B—C14B—C15B | 6.1 (2) |
C13A—N1A—C14A—N2A | −0.43 (14) | N1B—C14B—C15B—C16B | −128.32 (14) |
C13A—N1A—C14A—C15A | −177.57 (11) | N2B—C14B—C15B—C16B | 54.24 (18) |
C8A—N2A—C14A—N1A | −0.21 (14) | N1B—C14B—C15B—C20B | 48.37 (17) |
C7A—N2A—C14A—N1A | −172.67 (11) | N2B—C14B—C15B—C20B | −129.07 (13) |
C8A—N2A—C14A—C15A | 176.86 (11) | C20B—C15B—C16B—O3B | −177.02 (11) |
C7A—N2A—C14A—C15A | 4.4 (2) | C14B—C15B—C16B—O3B | −0.41 (19) |
N1A—C14A—C15A—C16A | −129.32 (14) | C20B—C15B—C16B—C17B | 1.92 (19) |
N2A—C14A—C15A—C16A | 53.91 (18) | C14B—C15B—C16B—C17B | 178.53 (12) |
N1A—C14A—C15A—C20A | 47.43 (17) | C24B—O4B—C17B—C18B | 12.40 (19) |
N2A—C14A—C15A—C20A | −129.35 (13) | C24B—O4B—C17B—C16B | −169.18 (12) |
C20A—C15A—C16A—O3A | −174.71 (11) | O3B—C16B—C17B—O4B | −1.57 (18) |
C14A—C15A—C16A—O3A | 1.95 (19) | C15B—C16B—C17B—O4B | 179.51 (11) |
C20A—C15A—C16A—C17A | 5.15 (19) | O3B—C16B—C17B—C18B | 176.93 (12) |
C14A—C15A—C16A—C17A | −178.18 (12) | C15B—C16B—C17B—C18B | −1.99 (19) |
C24A—O4A—C17A—C18A | 6.52 (19) | O4B—C17B—C18B—C19B | 179.27 (13) |
C24A—O4A—C17A—C16A | −175.33 (11) | C16B—C17B—C18B—C19B | 0.9 (2) |
O3A—C16A—C17A—O4A | −3.82 (18) | C17B—C18B—C19B—C20B | 0.2 (2) |
C15A—C16A—C17A—O4A | 176.31 (11) | C17B—C18B—C19B—C21B | 179.51 (12) |
O3A—C16A—C17A—C18A | 174.42 (12) | C18B—C19B—C20B—C15B | −0.25 (19) |
C15A—C16A—C17A—C18A | −5.44 (19) | C21B—C19B—C20B—C15B | −179.54 (12) |
O4A—C17A—C18A—C19A | 180.00 (12) | C16B—C15B—C20B—C19B | −0.83 (19) |
C16A—C17A—C18A—C19A | 2.0 (2) | C14B—C15B—C20B—C19B | −177.58 (12) |
C17A—C18A—C19A—C20A | 1.8 (2) | C20B—C19B—C21B—C22B | −8.9 (2) |
C17A—C18A—C19A—C21A | −177.46 (12) | C18B—C19B—C21B—C22B | 171.79 (12) |
C18A—C19A—C20A—C15A | −2.07 (19) | C19B—C21B—C22B—C23B | 124.11 (16) |
C21A—C19A—C20A—C15A | 177.17 (12) | C5B—C4B—C26B—C27B | 97.42 (15) |
C16A—C15A—C20A—C19A | −1.46 (19) | C3B—C4B—C26B—C27B | −81.78 (16) |
C14A—C15A—C20A—C19A | −178.33 (12) | C4B—C26B—C27B—C28B | 133.17 (15) |
C20A—C19A—C21A—C22A | −10.9 (2) | C33A—N3A—C29A—C30A | −0.1 (2) |
C18A—C19A—C21A—C22A | 168.38 (12) | N3A—C29A—C30A—C31A | −0.2 (2) |
C19A—C21A—C22A—C23A | 134.61 (14) | C29A—C30A—C31A—C32A | 0.6 (2) |
C5A—C4A—C26A—C27A | −72.15 (16) | C30A—C31A—C32A—C33A | −0.6 (2) |
C3A—C4A—C26A—C27A | 104.09 (15) | C29A—N3A—C33A—C32A | 0.1 (2) |
C4A—C26A—C27A—C28A | 107.50 (16) | C31A—C32A—C33A—N3A | 0.2 (2) |
C25B—O2B—C2B—C3B | 2.11 (18) | C33B—N3B—C29B—C30B | 0.9 (2) |
C25B—O2B—C2B—C1B | −178.42 (11) | N3B—C29B—C30B—C31B | −0.3 (2) |
O1B—C1B—C2B—O2B | −1.58 (18) | C29B—C30B—C31B—C32B | −0.5 (2) |
C6B—C1B—C2B—O2B | 178.70 (11) | C30B—C31B—C32B—C33B | 0.6 (2) |
O1B—C1B—C2B—C3B | 177.92 (12) | C29B—N3B—C33B—C32B | −0.8 (2) |
C6B—C1B—C2B—C3B | −1.80 (19) | C31B—C32B—C33B—N3B | 0.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1OA···O2A | 0.93 (2) | 2.30 (2) | 2.6977 (14) | 105 (1) |
O1A—H1OA···N1B | 0.93 (2) | 1.81 (2) | 2.6932 (15) | 157 (2) |
O3A—H3OA···O4A | 0.93 (2) | 2.25 (2) | 2.6798 (13) | 108 (2) |
O3A—H3OA···N3Bi | 0.93 (2) | 1.90 (2) | 2.7859 (14) | 160 (2) |
O1B—H1OB···O2B | 0.90 (2) | 2.33 (2) | 2.7197 (14) | 106 (2) |
O1B—H1OB···N1Aii | 0.90 (2) | 1.87 (2) | 2.7114 (15) | 153 (2) |
O3B—H3OB···O4B | 0.99 (2) | 2.27 (2) | 2.6789 (13) | 103 (1) |
O3B—H3OB···N3Aiii | 0.99 (2) | 1.68 (2) | 2.6461 (15) | 161 (2) |
C7A—H7A···O3A | 0.97 | 2.38 | 3.1017 (15) | 131 |
C7A—H7B···O1A | 0.97 | 2.35 | 2.7525 (16) | 104 |
C7B—H7C···O3B | 0.97 | 2.30 | 3.0302 (16) | 132 |
C7B—H7D···O1B | 0.97 | 2.35 | 2.7231 (16) | 102 |
C11B—H11B···O2Aiv | 0.93 | 2.59 | 3.5010 (17) | 165 |
C31A—H31A···O1A | 0.93 | 2.36 | 3.2382 (18) | 158 |
C23A—H23A···Cg1v | 0.93 | 2.90 | 3.3950 (17) | 115 |
C28B—H28C···Cg2vi | 0.93 | 2.99 | 3.4562 (18) | 113 |
C33A—H33A···Cg3i | 0.93 | 2.74 | 3.4888 (16) | 139 |
Symmetry codes: (i) x, y, z−1; (ii) x+1, y+1, z; (iii) −x+2, −y+1, −z; (iv) −x+2, −y+1, −z+1; (v) x−1, y, z; (vi) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C28H28N2O4·C5H5N |
Mr | 535.62 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 9.5355 (1), 17.3405 (3), 17.8604 (3) |
α, β, γ (°) | 92.840 (1), 105.372 (1), 102.523 (1) |
V (Å3) | 2761.80 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.40 × 0.27 × 0.23 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.967, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 44895, 16031, 11052 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.143, 1.10 |
No. of reflections | 16031 |
No. of parameters | 741 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.34, −0.29 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1OA···O2A | 0.93 (2) | 2.30 (2) | 2.6977 (14) | 105 (1) |
O1A—H1OA···N1B | 0.93 (2) | 1.81 (2) | 2.6932 (15) | 157 (2) |
O3A—H3OA···O4A | 0.93 (2) | 2.25 (2) | 2.6798 (13) | 108 (2) |
O3A—H3OA···N3Bi | 0.93 (2) | 1.90 (2) | 2.7859 (14) | 160 (2) |
O1B—H1OB···O2B | 0.90 (2) | 2.33 (2) | 2.7197 (14) | 106 (2) |
O1B—H1OB···N1Aii | 0.90 (2) | 1.87 (2) | 2.7114 (15) | 153 (2) |
O3B—H3OB···O4B | 0.99 (2) | 2.27 (2) | 2.6789 (13) | 103 (1) |
O3B—H3OB···N3Aiii | 0.99 (2) | 1.68 (2) | 2.6461 (15) | 161 (2) |
C7A—H7A···O3A | 0.97 | 2.38 | 3.1017 (15) | 131 |
C7A—H7B···O1A | 0.97 | 2.35 | 2.7525 (16) | 104 |
C7B—H7C···O3B | 0.97 | 2.30 | 3.0302 (16) | 132 |
C7B—H7D···O1B | 0.97 | 2.35 | 2.7231 (16) | 102 |
C11B—H11B···O2Aiv | 0.93 | 2.59 | 3.5010 (17) | 165 |
C31A—H31A···O1A | 0.93 | 2.36 | 3.2382 (18) | 158 |
C23A—H23A···Cg1v | 0.93 | 2.90 | 3.3950 (17) | 115 |
C28B—H28C···Cg2vi | 0.93 | 2.99 | 3.4562 (18) | 113 |
C33A—H33A···Cg3i | 0.93 | 2.74 | 3.4888 (16) | 139 |
Symmetry codes: (i) x, y, z−1; (ii) x+1, y+1, z; (iii) −x+2, −y+1, −z; (iv) −x+2, −y+1, −z+1; (v) x−1, y, z; (vi) −x+1, −y+1, −z+1. |
The synthesis of benzimidazoles has received much attention owing to their various biological activities such as antidiabetic (Minoura et al., 2004), antimicrobial, antifungal (Pawar et al., 2004), antiviral (Tomei et al., 2003), anti-HIV (Barreca et al., 2003), and anticancer (Demirayak et al., 2002). Recently, we reported the crystal structures of 2-(benzimidazol-2-yl)-6-methoxyphenol (Eltayeb et al., 2007a) and 2-(2-methoxynaphthalen-1-yl)-1-[(2-methoxynaphthalen-1-yl)methyl]-1H- benzimidazole (Eltayeb et al., 2007b). The title compound was synthesized as an extension of our investigations of benzimidazole derivatives. We report here the crystal structure of the title compound.
The title compound crystalizes with two molecules of the benzimidazole derivative [A and B] and two molecules of pyridine in the asymmetric unit. In both A and B, the benzimidazole ring system is essentially planar. The benzimidazole ring system makes dihedral angles of 85.35 (5)° and 50.51 (5)°, respectively, with the C1–C6 and C15—C20 benzene rings in molecule A, and 82.93 (5)° and 51.30 (5)°, respectively, in molecule B. The hydroxyl groups are coplanar with the attached benzene rings, whereas the methoxy groups are slightly twisted away from the mean plane of the attached benzene rings, as indicated by the C25–O2–C2–C3 [4.29 (18)° in molecule A and 2.11 (18)° in molecule B] and C24–O4–C17–C18 [6.52 (19)° in molecule A and 12.40 (19) ° in molecule B] torsion angles. The orientation of the allyl groups with respect to the attached benzene rings can be described by the torsion angle C3–C4–C26–C27 of 104.09 (15)° in molecule A [-81.78 (16)° in molecule B] and C18–C19–C21–C22 torsion angle of 168.38 (12)° in molecule A [171.79 (12)° in molecule B]. Bond lengths and angles in both molecules are in normal ranges (Allen et al., 1987) and are comparable to those in related structures (Eltayeb et al., 2007a; 2007b).
There are two O—H···O intramolecular hydrogen bonds involving the two hydroxyl and the two methoxyl groups [O1A—H1OA···O2A and O3A—H3OA···O4A in molecule A, and O1B—H1OB···O2B and O3B—H3OB···O4B in molecule B] (Table 1) which generate S(6) ring motifs. In addition, C—H···O intramolecular hydrogen bonds are also observed.
The crystal structure is stabilized by intermolecular O—H···N and C—H···O hydrogen bonds, which link the molecules into chains along the [1 1 0] direction (Fig. 2). The structure is further stabilized by intermolecular C—H···π interactions (Table 1), involving the N1A/C13A/C8A/N2A/C14A (centroid Cg1), C8A–C13A (centroid Cg2) and N3B/C29B—C33B (centroid Cg3) rings.