organic compounds
Ethyl 2-[4-(morpholin-4-yl)phenyl]-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-1,3-benzimidazole-5-carboxylate monohydrate
aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia, and bSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: arazaki@usm.my
The 27H32N4O4·H2O, contains two independent benzimidazole-5-carboxylate molecules and two water molecules. In both main molecules, the pyrrolidine rings are in an with a methylene C atom as the flap. The morpholine rings adopt chair conformations. Both benzimidazole rings are essentially planar, with maximum deviations of 0.008 (1) Å, and form dihedral angles of 37.65 (6) and 45.44 (6)° with the benzene rings. In one molecule, an intramolecular C—H⋯O hydrogen bond forms an S(7) ring motif. In the crystal, O—H⋯O and O—H⋯N hydrogen bonds connect pairs of main molecules and pairs of water molecules into two independent centrosymmetric four-compoment aggregates. These aggregates are connect by C—H⋯O hydrogen bonds leading to the formation of a three-dimensional network, which is stabilized by C—H⋯π interactions.
of the title compound, CRelated literature
For the biological activity of benzimidazoles, see: Townsend & Revankar (1970); Dubey & Sanyal (2010). For related structures, see: Yoon, Ali, Wei et al. (2011); Yoon et al. (2012); Yoon, Ali, Choon et al. (2011). For ring conformations, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); 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
https://doi.org/10.1107/S1600536812039268/lh5526sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039268/lh5526Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812039268/lh5526Isup3.cml
Ethyl 3-amino-4-(3(2-oxopyrrolidin-1yl)propylamino)benzoate (0.84 mmol) and sodium metabisulfite adduct of 4-morpholino benzaldehyde (1.68 mmol) were dissolved in DMF. The reaction mixture was reflux at 403K for 2 h. After completion, the reaction mixture was diluted in ethyl acetate (20 ml) and washed with water (20 ml). The organic layer was collected, dried over Na2SO4 and the evaporated in vacuo to yield the product. The product was recrystallized from ethyl acetate. The crystals were then removed and washed twice gently with cold ethyl acetate.
H atoms of the water molecules were located in a difference Fourier map and refined freely [O–H = 0.84 (3)–0.91 (3) Å]. All other H atoms were positioned geometrically [C–H = 0.95 and 0.99 Å] and refined using a riding model with Uiso(H) = 1.2 and 1.5 Ueq(C). A rotating group model was applied to the methyl groups. Two outliner reflections (0 0 1 and -9 - 2 12) were omitted in the final refinement.
Benzimidazoles belong to one of the well known and most extensively studied class of compounds due to their biological activities such as anti-cancer (Townsend & Revankar, 1970) and anthelmintics (Dubey & Sanyal, 2010). As part of our ongoing structural studies of benzimidazole derivatives (Yoon, Ali, Wei et al. 2011), we report herein the
of the title compound.The φ= 69.4 (4)° in which C21A is the flap and Q= 0.2563 (17) Å and φ= 71.7 (4)° in which C21B is the flap. The morpholine rings, O4A/N4A/C24A–C27A [puckering paramaters; Q = 0.4341 (18) Å, Θ= 1.1 (3)° and φ= 256 (10)°] and O4B/N4B/C24B–C27B [puckering paramaters; Q = 0.5605 (16) Å, Θ= 176.18 (16)° and φ= 153 (3)°] adopt chair conformations. The benzimidazole rings (N1A/N2A/C1A–C7A and N1B/N2B/C1B–C7B) are essentially planar with maximum deviation of 0.008 (1) Å at atom N2A, C6B and C7B. In molecule A, the benzimidazole ring, N1A/N2A/C1A–C7A, forms a dihedral of 37.65 (6)° with the benzene (C8A–C13A) ring. The corresponding dihedral angle in molecule B is 45.44 (6)°. In molecule B, an intramolecular C17A—H17B···O3A hydrogen bond (Table 1) forms S(7) ring motif (Bernstein et al., 1995). The bond lengths and angles are within normal ranges and comparable to the related structures (Yoon, Ali, Wei et al., 2011; Yoon et al., 2012; Yoon, Ali, Choon et al., 2011).
of the title compound, (Fig. 1), consists of two crystallographically independent (A and B) Ethyl 2-(4-morpholinophenyl)-1-(3-oxopyrolidin-1-yl) propyl)-1H-benzo [d]imidazole-5-carboxylate and two water molecules. In both molecules, the pyrrolidine rings (N3A/C20A–C23A & N3B/C20B–C23B) are in envelope conformations (Cremer & Pople, 1975) with puckering parameters, Q= 0.2575 (19) Å andIn the crystal packing (Fig. 2), intermolecular O—H···O, C—H···N and C—H···O hydrogen bonds (Table 1) link the molecules into a three-dimensional network. The intermolecular C13B—H13B···Cg1iii, C21B—H21D···Cg2, C24A—H24B···Cg3iii and C24B—H24D···Cg4vii (Table 1) interactions further stabilize the
(Cg1, Cg2, Cg3 and Cg4 are the centroids of N1A/N2A/C1A/C6A/C7A, C21B–C26B, C21A–C26A and C21B–C26B rings, respectively).For the biological activity of benzimidazoles, see: Townsend & Revankar (1970); Dubey & Sanyal (2010). For related structures, see: Yoon, Ali, Wei et al. (2011); Yoon et al. (2012); Yoon, Ali, Choon et al. (2011). For ring conformations, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids. The dashed line indicates a hydrogen bond. | |
Fig. 2. The crystal packing of the title compound. The H atoms not involved in the hydrogen bonds (dashed lines) have been omitted for clarity. |
C27H32N4O4·H2O | Z = 4 |
Mr = 494.58 | F(000) = 1056 |
Triclinic, P1 | Dx = 1.299 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 12.2602 (3) Å | Cell parameters from 9908 reflections |
b = 13.7267 (4) Å | θ = 2.5–33.5° |
c = 15.3163 (4) Å | µ = 0.09 mm−1 |
α = 99.357 (1)° | T = 100 K |
β = 93.700 (1)° | Plate, colourless |
γ = 94.003 (1)° | 0.67 × 0.40 × 0.11 mm |
V = 2529.56 (12) Å3 |
Bruker SMART APEXII CCD area-detector diffractometer | 14611 independent reflections |
Radiation source: fine-focus sealed tube | 10995 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
φ and ω scans | θmax = 30.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −17→17 |
Tmin = 0.942, Tmax = 0.991 | k = −19→19 |
61724 measured reflections | l = −21→21 |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.152 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0734P)2 + 1.0729P] where P = (Fo2 + 2Fc2)/3 |
14611 reflections | (Δ/σ)max = 0.001 |
667 parameters | Δρmax = 0.58 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
C27H32N4O4·H2O | γ = 94.003 (1)° |
Mr = 494.58 | V = 2529.56 (12) Å3 |
Triclinic, P1 | Z = 4 |
a = 12.2602 (3) Å | Mo Kα radiation |
b = 13.7267 (4) Å | µ = 0.09 mm−1 |
c = 15.3163 (4) Å | T = 100 K |
α = 99.357 (1)° | 0.67 × 0.40 × 0.11 mm |
β = 93.700 (1)° |
Bruker SMART APEXII CCD area-detector diffractometer | 14611 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 10995 reflections with I > 2σ(I) |
Tmin = 0.942, Tmax = 0.991 | Rint = 0.042 |
61724 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.152 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.58 e Å−3 |
14611 reflections | Δρmin = −0.37 e Å−3 |
667 parameters |
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 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 | 0.66537 (9) | 0.88724 (8) | 0.48359 (7) | 0.0207 (2) | |
O2A | 0.80726 (9) | 0.79642 (8) | 0.44866 (7) | 0.0229 (2) | |
O3A | 0.25226 (9) | 0.68922 (8) | −0.13551 (8) | 0.0235 (2) | |
O4A | 0.64255 (10) | 0.32281 (11) | −0.46338 (9) | 0.0396 (4) | |
N1A | 0.68276 (10) | 0.65123 (9) | 0.11445 (8) | 0.0147 (2) | |
N2A | 0.52634 (9) | 0.71947 (9) | 0.08170 (8) | 0.0150 (2) | |
N3A | 0.38761 (10) | 0.80132 (9) | −0.16261 (8) | 0.0184 (2) | |
N4A | 0.63208 (11) | 0.45033 (11) | −0.29891 (8) | 0.0240 (3) | |
C1A | 0.65487 (11) | 0.71291 (10) | 0.18925 (9) | 0.0138 (3) | |
C2A | 0.70794 (11) | 0.73504 (10) | 0.27435 (9) | 0.0152 (3) | |
H2AA | 0.7733 | 0.7058 | 0.2887 | 0.018* | |
C3A | 0.66221 (11) | 0.80115 (10) | 0.33738 (9) | 0.0157 (3) | |
C4A | 0.56478 (12) | 0.84465 (11) | 0.31643 (10) | 0.0178 (3) | |
H4AA | 0.5355 | 0.8896 | 0.3611 | 0.021* | |
C5A | 0.51084 (12) | 0.82345 (11) | 0.23243 (10) | 0.0182 (3) | |
H5AA | 0.4455 | 0.8528 | 0.2182 | 0.022* | |
C6A | 0.55780 (11) | 0.75645 (10) | 0.16971 (9) | 0.0152 (3) | |
C7A | 0.60465 (11) | 0.65698 (10) | 0.05185 (9) | 0.0142 (3) | |
C8A | 0.60534 (11) | 0.60341 (10) | −0.03932 (9) | 0.0141 (3) | |
C9A | 0.51195 (12) | 0.55865 (10) | −0.09139 (9) | 0.0165 (3) | |
H9AA | 0.4421 | 0.5637 | −0.0683 | 0.020* | |
C10A | 0.51939 (12) | 0.50689 (11) | −0.17616 (9) | 0.0172 (3) | |
H10A | 0.4546 | 0.4772 | −0.2103 | 0.021* | |
C11A | 0.62128 (12) | 0.49775 (11) | −0.21216 (9) | 0.0161 (3) | |
C12A | 0.71504 (12) | 0.54133 (11) | −0.15894 (9) | 0.0173 (3) | |
H12A | 0.7852 | 0.5356 | −0.1814 | 0.021* | |
C13A | 0.70707 (11) | 0.59237 (10) | −0.07463 (9) | 0.0163 (3) | |
H13A | 0.7719 | 0.6206 | −0.0398 | 0.020* | |
C14A | 0.72009 (12) | 0.82628 (11) | 0.42737 (9) | 0.0169 (3) | |
C15A | 0.71598 (14) | 0.91412 (12) | 0.57342 (10) | 0.0256 (3) | |
H15A | 0.7853 | 0.9559 | 0.5741 | 0.031* | |
H15B | 0.7323 | 0.8540 | 0.5982 | 0.031* | |
C16A | 0.63542 (16) | 0.97026 (15) | 0.62659 (12) | 0.0353 (4) | |
H16A | 0.6639 | 0.9859 | 0.6890 | 0.053* | |
H16B | 0.5655 | 0.9298 | 0.6218 | 0.053* | |
H16C | 0.6240 | 1.0318 | 0.6039 | 0.053* | |
C17A | 0.43840 (11) | 0.75615 (11) | 0.02944 (9) | 0.0160 (3) | |
H17A | 0.3789 | 0.7748 | 0.0680 | 0.019* | |
H17B | 0.4077 | 0.7024 | −0.0188 | 0.019* | |
C18A | 0.47845 (12) | 0.84531 (11) | −0.01077 (10) | 0.0187 (3) | |
H18A | 0.5468 | 0.8313 | −0.0398 | 0.022* | |
H18B | 0.4952 | 0.9034 | 0.0369 | 0.022* | |
C19A | 0.39221 (13) | 0.86937 (11) | −0.07883 (10) | 0.0204 (3) | |
H19A | 0.3194 | 0.8663 | −0.0545 | 0.025* | |
H19B | 0.4093 | 0.9378 | −0.0896 | 0.025* | |
C20A | 0.45280 (15) | 0.82253 (13) | −0.23446 (11) | 0.0293 (4) | |
H20A | 0.5303 | 0.8422 | −0.2127 | 0.035* | |
H20B | 0.4232 | 0.8759 | −0.2630 | 0.035* | |
C21A | 0.44200 (16) | 0.72360 (14) | −0.29895 (12) | 0.0328 (4) | |
H21A | 0.4393 | 0.7345 | −0.3613 | 0.039* | |
H21B | 0.5040 | 0.6835 | −0.2880 | 0.039* | |
C22A | 0.33378 (14) | 0.67318 (13) | −0.27850 (11) | 0.0270 (3) | |
H22A | 0.2727 | 0.6857 | −0.3196 | 0.032* | |
H22B | 0.3381 | 0.6008 | −0.2833 | 0.032* | |
C23A | 0.31818 (12) | 0.71960 (11) | −0.18452 (10) | 0.0185 (3) | |
C24A | 0.53510 (13) | 0.41985 (14) | −0.35701 (11) | 0.0285 (4) | |
H24A | 0.4881 | 0.4759 | −0.3547 | 0.034* | |
H24B | 0.4935 | 0.3650 | −0.3357 | 0.034* | |
C25A | 0.55943 (15) | 0.38658 (17) | −0.45059 (11) | 0.0380 (5) | |
H25A | 0.4914 | 0.3532 | −0.4838 | 0.046* | |
H25B | 0.5793 | 0.4460 | −0.4770 | 0.046* | |
C26A | 0.73703 (15) | 0.35354 (15) | −0.40709 (11) | 0.0340 (4) | |
H26A | 0.7760 | 0.4099 | −0.4281 | 0.041* | |
H26B | 0.7858 | 0.2987 | −0.4120 | 0.041* | |
C27A | 0.71833 (14) | 0.38407 (13) | −0.31218 (11) | 0.0283 (4) | |
H27A | 0.6992 | 0.3242 | −0.2862 | 0.034* | |
H27B | 0.7872 | 0.4172 | −0.2802 | 0.034* | |
O1B | 0.17128 (9) | 0.40808 (8) | 0.45880 (7) | 0.0202 (2) | |
O2B | 0.32510 (9) | 0.33404 (8) | 0.42527 (7) | 0.0232 (2) | |
O3B | −0.23642 (9) | 0.17337 (8) | −0.16601 (8) | 0.0231 (2) | |
O4B | 0.12139 (10) | −0.16714 (9) | −0.48934 (7) | 0.0254 (2) | |
N1B | 0.20016 (10) | 0.15817 (9) | 0.09803 (8) | 0.0146 (2) | |
N2B | 0.04049 (9) | 0.21890 (9) | 0.06163 (8) | 0.0143 (2) | |
N3B | −0.09212 (10) | 0.28326 (9) | −0.18049 (8) | 0.0173 (2) | |
N4B | 0.13616 (10) | −0.08559 (9) | −0.30449 (8) | 0.0177 (2) | |
C1B | 0.17154 (11) | 0.22424 (10) | 0.16978 (9) | 0.0134 (3) | |
C2B | 0.22552 (11) | 0.25486 (10) | 0.25383 (9) | 0.0151 (3) | |
H2BA | 0.2930 | 0.2298 | 0.2698 | 0.018* | |
C3B | 0.17737 (11) | 0.32329 (10) | 0.31350 (9) | 0.0157 (3) | |
C4B | 0.07777 (12) | 0.36160 (11) | 0.28975 (9) | 0.0175 (3) | |
H4BA | 0.0473 | 0.4086 | 0.3320 | 0.021* | |
C5B | 0.02341 (12) | 0.33243 (11) | 0.20668 (9) | 0.0176 (3) | |
H5BA | −0.0434 | 0.3584 | 0.1905 | 0.021* | |
C6B | 0.07180 (11) | 0.26286 (10) | 0.14780 (9) | 0.0145 (3) | |
C7B | 0.12087 (11) | 0.15719 (10) | 0.03483 (9) | 0.0138 (3) | |
C8B | 0.11987 (11) | 0.09680 (10) | −0.05387 (9) | 0.0141 (3) | |
C9B | 0.02794 (12) | 0.03843 (10) | −0.09653 (9) | 0.0156 (3) | |
H9BA | −0.0393 | 0.0395 | −0.0690 | 0.019* | |
C10B | 0.03271 (12) | −0.02111 (11) | −0.17829 (9) | 0.0166 (3) | |
H10B | −0.0311 | −0.0607 | −0.2051 | 0.020* | |
C11B | 0.12970 (12) | −0.02411 (10) | −0.22224 (9) | 0.0153 (3) | |
C12B | 0.22229 (12) | 0.03535 (11) | −0.17892 (9) | 0.0175 (3) | |
H12B | 0.2894 | 0.0354 | −0.2067 | 0.021* | |
C13B | 0.21727 (11) | 0.09352 (10) | −0.09678 (9) | 0.0163 (3) | |
H13B | 0.2813 | 0.1320 | −0.0689 | 0.020* | |
C14B | 0.23436 (12) | 0.35468 (11) | 0.40338 (9) | 0.0172 (3) | |
C15B | 0.21555 (13) | 0.43897 (12) | 0.55009 (10) | 0.0223 (3) | |
H15C | 0.2702 | 0.4965 | 0.5547 | 0.027* | |
H15D | 0.2516 | 0.3843 | 0.5719 | 0.027* | |
C16B | 0.12101 (16) | 0.46633 (18) | 0.60303 (12) | 0.0411 (5) | |
H16D | 0.1471 | 0.4870 | 0.6656 | 0.062* | |
H16E | 0.0672 | 0.4090 | 0.5972 | 0.062* | |
H16F | 0.0867 | 0.5210 | 0.5811 | 0.062* | |
C17B | −0.05096 (11) | 0.24722 (11) | 0.00739 (9) | 0.0158 (3) | |
H17C | −0.1156 | 0.2538 | 0.0428 | 0.019* | |
H17D | −0.0706 | 0.1942 | −0.0444 | 0.019* | |
C18B | −0.02321 (13) | 0.34433 (11) | −0.02516 (10) | 0.0195 (3) | |
H18C | 0.0522 | 0.3455 | −0.0448 | 0.023* | |
H18D | −0.0259 | 0.4003 | 0.0241 | 0.023* | |
C19B | −0.10395 (13) | 0.35643 (11) | −0.10218 (10) | 0.0206 (3) | |
H19C | −0.1798 | 0.3491 | −0.0842 | 0.025* | |
H19D | −0.0910 | 0.4238 | −0.1167 | 0.025* | |
C20B | −0.00713 (13) | 0.29695 (12) | −0.24108 (11) | 0.0254 (3) | |
H20C | 0.0648 | 0.3189 | −0.2080 | 0.030* | |
H20D | −0.0262 | 0.3462 | −0.2790 | 0.030* | |
C21B | −0.00526 (13) | 0.19367 (13) | −0.29671 (11) | 0.0256 (3) | |
H21C | 0.0088 | 0.1982 | −0.3589 | 0.031* | |
H21D | 0.0516 | 0.1561 | −0.2716 | 0.031* | |
C22B | −0.11994 (13) | 0.14519 (12) | −0.29112 (10) | 0.0217 (3) | |
H22C | −0.1693 | 0.1531 | −0.3428 | 0.026* | |
H22D | −0.1175 | 0.0737 | −0.2889 | 0.026* | |
C23B | −0.15789 (11) | 0.19944 (11) | −0.20610 (9) | 0.0171 (3) | |
C24B | 0.03344 (13) | −0.13261 (12) | −0.35087 (10) | 0.0226 (3) | |
H24C | −0.0104 | −0.0815 | −0.3712 | 0.027* | |
H24D | −0.0095 | −0.1652 | −0.3095 | 0.027* | |
C25B | 0.05476 (14) | −0.20895 (12) | −0.43018 (11) | 0.0254 (3) | |
H25C | 0.0915 | −0.2637 | −0.4091 | 0.030* | |
H25D | −0.0161 | −0.2369 | −0.4622 | 0.030* | |
C26B | 0.22365 (14) | −0.12744 (12) | −0.44363 (10) | 0.0247 (3) | |
H26C | 0.2709 | −0.0998 | −0.4852 | 0.030* | |
H26D | 0.2613 | −0.1810 | −0.4212 | 0.030* | |
C27B | 0.20697 (14) | −0.04717 (12) | −0.36697 (10) | 0.0236 (3) | |
H27C | 0.2789 | −0.0211 | −0.3358 | 0.028* | |
H27D | 0.1731 | 0.0081 | −0.3898 | 0.028* | |
O1WA | 0.34451 (10) | 1.00467 (10) | 0.12704 (10) | 0.0318 (3) | |
O1WB | 0.83897 (11) | 0.50664 (10) | 0.14244 (12) | 0.0425 (4) | |
H1WA | 0.303 (2) | 0.955 (2) | 0.1401 (16) | 0.052 (7)* | |
H2WA | 0.295 (2) | 1.048 (2) | 0.1147 (17) | 0.061 (8)* | |
H1WB | 0.790 (2) | 0.5461 (19) | 0.1295 (16) | 0.052 (7)* | |
H2WB | 0.808 (2) | 0.450 (2) | 0.1384 (17) | 0.054 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0249 (5) | 0.0226 (5) | 0.0130 (5) | 0.0054 (4) | 0.0001 (4) | −0.0023 (4) |
O2A | 0.0218 (5) | 0.0278 (6) | 0.0175 (5) | 0.0051 (4) | −0.0023 (4) | −0.0006 (4) |
O3A | 0.0185 (5) | 0.0212 (5) | 0.0304 (6) | −0.0006 (4) | 0.0018 (4) | 0.0040 (5) |
O4A | 0.0298 (7) | 0.0514 (8) | 0.0284 (7) | 0.0123 (6) | −0.0044 (5) | −0.0222 (6) |
N1A | 0.0156 (5) | 0.0144 (5) | 0.0133 (5) | 0.0020 (4) | 0.0000 (4) | 0.0005 (4) |
N2A | 0.0155 (5) | 0.0162 (5) | 0.0127 (5) | 0.0034 (4) | −0.0012 (4) | 0.0005 (4) |
N3A | 0.0197 (6) | 0.0190 (6) | 0.0154 (6) | −0.0020 (5) | −0.0026 (5) | 0.0025 (5) |
N4A | 0.0200 (6) | 0.0367 (8) | 0.0131 (6) | 0.0121 (6) | −0.0037 (5) | −0.0044 (5) |
C1A | 0.0136 (6) | 0.0132 (6) | 0.0140 (6) | 0.0018 (5) | 0.0004 (5) | 0.0006 (5) |
C2A | 0.0134 (6) | 0.0169 (6) | 0.0151 (7) | 0.0018 (5) | −0.0004 (5) | 0.0021 (5) |
C3A | 0.0157 (6) | 0.0166 (6) | 0.0136 (6) | −0.0002 (5) | 0.0000 (5) | 0.0004 (5) |
C4A | 0.0180 (7) | 0.0186 (7) | 0.0160 (7) | 0.0039 (5) | 0.0018 (5) | −0.0010 (5) |
C5A | 0.0154 (6) | 0.0200 (7) | 0.0184 (7) | 0.0056 (5) | −0.0007 (5) | 0.0001 (5) |
C6A | 0.0142 (6) | 0.0153 (6) | 0.0156 (7) | 0.0010 (5) | −0.0004 (5) | 0.0018 (5) |
C7A | 0.0145 (6) | 0.0124 (6) | 0.0153 (6) | 0.0006 (5) | −0.0001 (5) | 0.0017 (5) |
C8A | 0.0166 (6) | 0.0124 (6) | 0.0131 (6) | 0.0019 (5) | 0.0000 (5) | 0.0020 (5) |
C9A | 0.0158 (6) | 0.0184 (7) | 0.0150 (7) | 0.0002 (5) | 0.0010 (5) | 0.0027 (5) |
C10A | 0.0163 (6) | 0.0196 (7) | 0.0147 (7) | 0.0000 (5) | −0.0019 (5) | 0.0011 (5) |
C11A | 0.0184 (6) | 0.0185 (7) | 0.0119 (6) | 0.0048 (5) | −0.0003 (5) | 0.0034 (5) |
C12A | 0.0152 (6) | 0.0213 (7) | 0.0159 (7) | 0.0040 (5) | 0.0018 (5) | 0.0035 (5) |
C13A | 0.0141 (6) | 0.0177 (6) | 0.0169 (7) | 0.0023 (5) | −0.0006 (5) | 0.0023 (5) |
C14A | 0.0184 (6) | 0.0167 (6) | 0.0146 (7) | 0.0002 (5) | 0.0016 (5) | 0.0005 (5) |
C15A | 0.0358 (9) | 0.0258 (8) | 0.0131 (7) | 0.0072 (7) | −0.0028 (6) | −0.0033 (6) |
C16A | 0.0399 (10) | 0.0419 (11) | 0.0213 (8) | 0.0027 (8) | 0.0081 (7) | −0.0047 (7) |
C17A | 0.0135 (6) | 0.0189 (7) | 0.0152 (7) | 0.0038 (5) | −0.0027 (5) | 0.0024 (5) |
C18A | 0.0201 (7) | 0.0163 (6) | 0.0181 (7) | −0.0003 (5) | −0.0049 (5) | 0.0013 (5) |
C19A | 0.0254 (7) | 0.0141 (6) | 0.0203 (7) | 0.0020 (6) | −0.0060 (6) | 0.0012 (5) |
C20A | 0.0312 (9) | 0.0318 (9) | 0.0245 (8) | −0.0057 (7) | 0.0041 (7) | 0.0061 (7) |
C21A | 0.0381 (10) | 0.0381 (10) | 0.0214 (8) | 0.0013 (8) | 0.0082 (7) | 0.0010 (7) |
C22A | 0.0326 (9) | 0.0273 (8) | 0.0178 (7) | −0.0010 (7) | −0.0050 (6) | −0.0015 (6) |
C23A | 0.0162 (6) | 0.0180 (7) | 0.0204 (7) | 0.0008 (5) | −0.0052 (5) | 0.0036 (5) |
C24A | 0.0185 (7) | 0.0396 (10) | 0.0218 (8) | 0.0042 (7) | −0.0040 (6) | −0.0094 (7) |
C25A | 0.0316 (9) | 0.0608 (13) | 0.0186 (8) | 0.0215 (9) | −0.0048 (7) | −0.0074 (8) |
C26A | 0.0340 (9) | 0.0451 (11) | 0.0210 (8) | 0.0200 (8) | −0.0024 (7) | −0.0054 (7) |
C27A | 0.0281 (8) | 0.0307 (9) | 0.0233 (8) | 0.0136 (7) | −0.0038 (6) | −0.0065 (7) |
O1B | 0.0226 (5) | 0.0223 (5) | 0.0136 (5) | 0.0063 (4) | −0.0013 (4) | −0.0044 (4) |
O2B | 0.0198 (5) | 0.0301 (6) | 0.0170 (5) | 0.0051 (4) | −0.0046 (4) | −0.0032 (4) |
O3B | 0.0177 (5) | 0.0255 (6) | 0.0272 (6) | −0.0001 (4) | 0.0021 (4) | 0.0081 (5) |
O4B | 0.0312 (6) | 0.0290 (6) | 0.0141 (5) | 0.0029 (5) | 0.0024 (4) | −0.0023 (4) |
N1B | 0.0174 (5) | 0.0146 (5) | 0.0112 (5) | 0.0029 (4) | −0.0010 (4) | −0.0001 (4) |
N2B | 0.0140 (5) | 0.0163 (5) | 0.0117 (5) | 0.0021 (4) | −0.0019 (4) | −0.0001 (4) |
N3B | 0.0165 (6) | 0.0202 (6) | 0.0149 (6) | 0.0002 (5) | −0.0010 (4) | 0.0037 (5) |
N4B | 0.0205 (6) | 0.0201 (6) | 0.0107 (5) | −0.0014 (5) | 0.0011 (4) | −0.0017 (4) |
C1B | 0.0144 (6) | 0.0131 (6) | 0.0117 (6) | 0.0016 (5) | −0.0003 (5) | −0.0003 (5) |
C2B | 0.0148 (6) | 0.0165 (6) | 0.0131 (6) | 0.0027 (5) | −0.0016 (5) | 0.0007 (5) |
C3B | 0.0158 (6) | 0.0174 (6) | 0.0128 (6) | 0.0018 (5) | −0.0008 (5) | −0.0001 (5) |
C4B | 0.0167 (6) | 0.0199 (7) | 0.0147 (7) | 0.0051 (5) | 0.0008 (5) | −0.0018 (5) |
C5B | 0.0152 (6) | 0.0210 (7) | 0.0160 (7) | 0.0055 (5) | −0.0004 (5) | 0.0003 (5) |
C6B | 0.0143 (6) | 0.0160 (6) | 0.0124 (6) | 0.0010 (5) | −0.0018 (5) | 0.0008 (5) |
C7B | 0.0153 (6) | 0.0122 (6) | 0.0133 (6) | 0.0001 (5) | −0.0006 (5) | 0.0014 (5) |
C8B | 0.0172 (6) | 0.0134 (6) | 0.0109 (6) | 0.0015 (5) | −0.0011 (5) | 0.0009 (5) |
C9B | 0.0178 (6) | 0.0168 (6) | 0.0119 (6) | −0.0010 (5) | 0.0016 (5) | 0.0024 (5) |
C10B | 0.0184 (6) | 0.0172 (6) | 0.0128 (6) | −0.0026 (5) | −0.0009 (5) | 0.0009 (5) |
C11B | 0.0206 (7) | 0.0153 (6) | 0.0096 (6) | 0.0016 (5) | −0.0013 (5) | 0.0015 (5) |
C12B | 0.0158 (6) | 0.0211 (7) | 0.0148 (7) | 0.0018 (5) | 0.0008 (5) | 0.0008 (5) |
C13B | 0.0153 (6) | 0.0170 (6) | 0.0155 (7) | 0.0002 (5) | −0.0014 (5) | 0.0008 (5) |
C14B | 0.0189 (7) | 0.0176 (6) | 0.0136 (6) | 0.0017 (5) | 0.0001 (5) | −0.0017 (5) |
C15B | 0.0289 (8) | 0.0231 (7) | 0.0121 (7) | 0.0029 (6) | −0.0027 (6) | −0.0045 (5) |
C16B | 0.0360 (10) | 0.0642 (14) | 0.0193 (9) | 0.0046 (9) | 0.0058 (7) | −0.0061 (8) |
C17B | 0.0132 (6) | 0.0197 (7) | 0.0142 (6) | 0.0026 (5) | −0.0032 (5) | 0.0031 (5) |
C18B | 0.0235 (7) | 0.0165 (7) | 0.0173 (7) | 0.0023 (5) | −0.0059 (6) | 0.0014 (5) |
C19B | 0.0247 (7) | 0.0190 (7) | 0.0178 (7) | 0.0058 (6) | −0.0039 (6) | 0.0025 (5) |
C20B | 0.0234 (8) | 0.0283 (8) | 0.0242 (8) | −0.0039 (6) | 0.0050 (6) | 0.0051 (6) |
C21B | 0.0246 (8) | 0.0320 (9) | 0.0200 (8) | 0.0021 (7) | 0.0062 (6) | 0.0021 (6) |
C22B | 0.0247 (7) | 0.0249 (8) | 0.0147 (7) | 0.0007 (6) | −0.0020 (6) | 0.0026 (6) |
C23B | 0.0148 (6) | 0.0209 (7) | 0.0160 (7) | 0.0016 (5) | −0.0042 (5) | 0.0062 (5) |
C24B | 0.0218 (7) | 0.0264 (8) | 0.0164 (7) | −0.0013 (6) | −0.0006 (6) | −0.0039 (6) |
C25B | 0.0272 (8) | 0.0260 (8) | 0.0196 (8) | −0.0015 (6) | 0.0000 (6) | −0.0044 (6) |
C26B | 0.0288 (8) | 0.0247 (8) | 0.0188 (7) | 0.0007 (6) | 0.0060 (6) | −0.0023 (6) |
C27B | 0.0296 (8) | 0.0220 (7) | 0.0176 (7) | −0.0023 (6) | 0.0070 (6) | −0.0012 (6) |
O1WA | 0.0230 (6) | 0.0226 (6) | 0.0512 (8) | 0.0041 (5) | −0.0005 (6) | 0.0104 (6) |
O1WB | 0.0237 (6) | 0.0195 (6) | 0.0827 (12) | 0.0014 (5) | −0.0133 (7) | 0.0104 (7) |
O1A—C14A | 1.3455 (17) | O2B—C14B | 1.2070 (17) |
O1A—C15A | 1.4515 (18) | O3B—C23B | 1.2377 (18) |
O2A—C14A | 1.2149 (18) | O4B—C25B | 1.420 (2) |
O3A—C23A | 1.2344 (19) | O4B—C26B | 1.4235 (19) |
O4A—C25A | 1.392 (2) | N1B—C7B | 1.3247 (17) |
O4A—C26A | 1.396 (2) | N1B—C1B | 1.3869 (17) |
N1A—C7A | 1.3264 (17) | N2B—C6B | 1.3773 (17) |
N1A—C1A | 1.3864 (17) | N2B—C7B | 1.3830 (18) |
N2A—C6A | 1.3808 (17) | N2B—C17B | 1.4642 (17) |
N2A—C7A | 1.3824 (17) | N3B—C23B | 1.3456 (18) |
N2A—C17A | 1.4669 (17) | N3B—C19B | 1.4558 (19) |
N3A—C23A | 1.3427 (18) | N3B—C20B | 1.462 (2) |
N3A—C19A | 1.4546 (19) | N4B—C11B | 1.4080 (17) |
N3A—C20A | 1.456 (2) | N4B—C24B | 1.4591 (18) |
N4A—C11A | 1.4001 (18) | N4B—C27B | 1.468 (2) |
N4A—C24A | 1.4330 (19) | C1B—C2B | 1.3953 (18) |
N4A—C27A | 1.445 (2) | C1B—C6B | 1.4089 (18) |
C1A—C2A | 1.3959 (18) | C2B—C3B | 1.3906 (19) |
C1A—C6A | 1.4053 (18) | C2B—H2BA | 0.9500 |
C2A—C3A | 1.3877 (19) | C3B—C4B | 1.4124 (19) |
C2A—H2AA | 0.9500 | C3B—C14B | 1.4865 (19) |
C3A—C4A | 1.4138 (19) | C4B—C5B | 1.3824 (19) |
C3A—C14A | 1.4857 (19) | C4B—H4BA | 0.9500 |
C4A—C5A | 1.3852 (19) | C5B—C6B | 1.3947 (19) |
C4A—H4AA | 0.9500 | C5B—H5BA | 0.9500 |
C5A—C6A | 1.3993 (19) | C7B—C8B | 1.4707 (18) |
C5A—H5AA | 0.9500 | C8B—C9B | 1.3957 (18) |
C7A—C8A | 1.4694 (19) | C8B—C13B | 1.400 (2) |
C8A—C9A | 1.3961 (18) | C9B—C10B | 1.3867 (19) |
C8A—C13A | 1.3992 (19) | C9B—H9BA | 0.9500 |
C9A—C10A | 1.387 (2) | C10B—C11B | 1.404 (2) |
C9A—H9AA | 0.9500 | C10B—H10B | 0.9500 |
C10A—C11A | 1.403 (2) | C11B—C12B | 1.4115 (19) |
C10A—H10A | 0.9500 | C12B—C13B | 1.3835 (19) |
C11A—C12A | 1.4029 (19) | C12B—H12B | 0.9500 |
C12A—C13A | 1.378 (2) | C13B—H13B | 0.9500 |
C12A—H12A | 0.9500 | C15B—C16B | 1.492 (2) |
C13A—H13A | 0.9500 | C15B—H15C | 0.9900 |
C15A—C16A | 1.496 (2) | C15B—H15D | 0.9900 |
C15A—H15A | 0.9900 | C16B—H16D | 0.9800 |
C15A—H15B | 0.9900 | C16B—H16E | 0.9800 |
C16A—H16A | 0.9800 | C16B—H16F | 0.9800 |
C16A—H16B | 0.9800 | C17B—C18B | 1.522 (2) |
C16A—H16C | 0.9800 | C17B—H17C | 0.9900 |
C17A—C18A | 1.523 (2) | C17B—H17D | 0.9900 |
C17A—H17A | 0.9900 | C18B—C19B | 1.5281 (19) |
C17A—H17B | 0.9900 | C18B—H18C | 0.9900 |
C18A—C19A | 1.5271 (19) | C18B—H18D | 0.9900 |
C18A—H18A | 0.9900 | C19B—H19C | 0.9900 |
C18A—H18B | 0.9900 | C19B—H19D | 0.9900 |
C19A—H19A | 0.9900 | C20B—C21B | 1.533 (2) |
C19A—H19B | 0.9900 | C20B—H20C | 0.9900 |
C20A—C21A | 1.536 (2) | C20B—H20D | 0.9900 |
C20A—H20A | 0.9900 | C21B—C22B | 1.527 (2) |
C20A—H20B | 0.9900 | C21B—H21C | 0.9900 |
C21A—C22A | 1.528 (3) | C21B—H21D | 0.9900 |
C21A—H21A | 0.9900 | C22B—C23B | 1.509 (2) |
C21A—H21B | 0.9900 | C22B—H22C | 0.9900 |
C22A—C23A | 1.506 (2) | C22B—H22D | 0.9900 |
C22A—H22A | 0.9900 | C24B—C25B | 1.519 (2) |
C22A—H22B | 0.9900 | C24B—H24C | 0.9900 |
C24A—C25A | 1.488 (2) | C24B—H24D | 0.9900 |
C24A—H24A | 0.9900 | C25B—H25C | 0.9900 |
C24A—H24B | 0.9900 | C25B—H25D | 0.9900 |
C25A—H25A | 0.9900 | C26B—C27B | 1.509 (2) |
C25A—H25B | 0.9900 | C26B—H26C | 0.9900 |
C26A—C27A | 1.483 (2) | C26B—H26D | 0.9900 |
C26A—H26A | 0.9900 | C27B—H27C | 0.9900 |
C26A—H26B | 0.9900 | C27B—H27D | 0.9900 |
C27A—H27A | 0.9900 | O1WA—H1WA | 0.88 (3) |
C27A—H27B | 0.9900 | O1WA—H2WA | 0.91 (3) |
O1B—C14B | 1.3482 (17) | O1WB—H1WB | 0.87 (3) |
O1B—C15B | 1.4514 (17) | O1WB—H2WB | 0.84 (3) |
C14A—O1A—C15A | 115.63 (12) | C25B—O4B—C26B | 109.43 (12) |
C25A—O4A—C26A | 113.58 (13) | C7B—N1B—C1B | 105.19 (11) |
C7A—N1A—C1A | 105.09 (11) | C6B—N2B—C7B | 106.63 (11) |
C6A—N2A—C7A | 106.39 (11) | C6B—N2B—C17B | 124.46 (11) |
C6A—N2A—C17A | 124.43 (11) | C7B—N2B—C17B | 128.17 (11) |
C7A—N2A—C17A | 128.26 (12) | C23B—N3B—C19B | 124.77 (13) |
C23A—N3A—C19A | 124.63 (13) | C23B—N3B—C20B | 113.41 (12) |
C23A—N3A—C20A | 113.69 (13) | C19B—N3B—C20B | 121.79 (12) |
C19A—N3A—C20A | 121.42 (13) | C11B—N4B—C24B | 117.25 (12) |
C11A—N4A—C24A | 118.85 (13) | C11B—N4B—C27B | 116.73 (12) |
C11A—N4A—C27A | 117.46 (12) | C24B—N4B—C27B | 110.38 (12) |
C24A—N4A—C27A | 113.95 (13) | N1B—C1B—C2B | 130.21 (12) |
N1A—C1A—C2A | 129.91 (12) | N1B—C1B—C6B | 109.88 (11) |
N1A—C1A—C6A | 109.98 (12) | C2B—C1B—C6B | 119.91 (12) |
C2A—C1A—C6A | 120.11 (12) | C3B—C2B—C1B | 117.82 (12) |
C3A—C2A—C1A | 117.90 (12) | C3B—C2B—H2BA | 121.1 |
C3A—C2A—H2AA | 121.0 | C1B—C2B—H2BA | 121.1 |
C1A—C2A—H2AA | 121.0 | C2B—C3B—C4B | 121.27 (12) |
C2A—C3A—C4A | 121.23 (13) | C2B—C3B—C14B | 117.65 (12) |
C2A—C3A—C14A | 117.83 (12) | C4B—C3B—C14B | 121.07 (12) |
C4A—C3A—C14A | 120.93 (12) | C5B—C4B—C3B | 121.69 (13) |
C5A—C4A—C3A | 121.70 (13) | C5B—C4B—H4BA | 119.2 |
C5A—C4A—H4AA | 119.1 | C3B—C4B—H4BA | 119.2 |
C3A—C4A—H4AA | 119.1 | C4B—C5B—C6B | 116.50 (13) |
C4A—C5A—C6A | 116.38 (13) | C4B—C5B—H5BA | 121.8 |
C4A—C5A—H5AA | 121.8 | C6B—C5B—H5BA | 121.8 |
C6A—C5A—H5AA | 121.8 | N2B—C6B—C5B | 131.51 (13) |
N2A—C6A—C5A | 131.51 (13) | N2B—C6B—C1B | 105.69 (12) |
N2A—C6A—C1A | 105.81 (12) | C5B—C6B—C1B | 122.80 (12) |
C5A—C6A—C1A | 122.68 (13) | N1B—C7B—N2B | 112.61 (12) |
N1A—C7A—N2A | 112.72 (12) | N1B—C7B—C8B | 123.05 (12) |
N1A—C7A—C8A | 122.28 (12) | N2B—C7B—C8B | 124.34 (12) |
N2A—C7A—C8A | 124.98 (12) | C9B—C8B—C13B | 117.60 (12) |
C9A—C8A—C13A | 117.83 (12) | C9B—C8B—C7B | 123.58 (13) |
C9A—C8A—C7A | 124.42 (13) | C13B—C8B—C7B | 118.75 (12) |
C13A—C8A—C7A | 117.68 (12) | C10B—C9B—C8B | 121.37 (13) |
C10A—C9A—C8A | 121.15 (13) | C10B—C9B—H9BA | 119.3 |
C10A—C9A—H9AA | 119.4 | C8B—C9B—H9BA | 119.3 |
C8A—C9A—H9AA | 119.4 | C9B—C10B—C11B | 121.43 (13) |
C9A—C10A—C11A | 120.90 (13) | C9B—C10B—H10B | 119.3 |
C9A—C10A—H10A | 119.5 | C11B—C10B—H10B | 119.3 |
C11A—C10A—H10A | 119.5 | C10B—C11B—N4B | 121.98 (12) |
N4A—C11A—C12A | 119.47 (13) | C10B—C11B—C12B | 116.94 (12) |
N4A—C11A—C10A | 122.80 (13) | N4B—C11B—C12B | 121.06 (13) |
C12A—C11A—C10A | 117.70 (13) | C13B—C12B—C11B | 121.28 (13) |
C13A—C12A—C11A | 121.08 (13) | C13B—C12B—H12B | 119.4 |
C13A—C12A—H12A | 119.5 | C11B—C12B—H12B | 119.4 |
C11A—C12A—H12A | 119.5 | C12B—C13B—C8B | 121.37 (13) |
C12A—C13A—C8A | 121.31 (13) | C12B—C13B—H13B | 119.3 |
C12A—C13A—H13A | 119.3 | C8B—C13B—H13B | 119.3 |
C8A—C13A—H13A | 119.3 | O2B—C14B—O1B | 123.61 (13) |
O2A—C14A—O1A | 123.10 (13) | O2B—C14B—C3B | 124.76 (13) |
O2A—C14A—C3A | 124.59 (13) | O1B—C14B—C3B | 111.62 (12) |
O1A—C14A—C3A | 112.30 (12) | O1B—C15B—C16B | 106.61 (13) |
O1A—C15A—C16A | 106.53 (14) | O1B—C15B—H15C | 110.4 |
O1A—C15A—H15A | 110.4 | C16B—C15B—H15C | 110.4 |
C16A—C15A—H15A | 110.4 | O1B—C15B—H15D | 110.4 |
O1A—C15A—H15B | 110.4 | C16B—C15B—H15D | 110.4 |
C16A—C15A—H15B | 110.4 | H15C—C15B—H15D | 108.6 |
H15A—C15A—H15B | 108.6 | C15B—C16B—H16D | 109.5 |
C15A—C16A—H16A | 109.5 | C15B—C16B—H16E | 109.5 |
C15A—C16A—H16B | 109.5 | H16D—C16B—H16E | 109.5 |
H16A—C16A—H16B | 109.5 | C15B—C16B—H16F | 109.5 |
C15A—C16A—H16C | 109.5 | H16D—C16B—H16F | 109.5 |
H16A—C16A—H16C | 109.5 | H16E—C16B—H16F | 109.5 |
H16B—C16A—H16C | 109.5 | N2B—C17B—C18B | 112.14 (11) |
N2A—C17A—C18A | 112.28 (11) | N2B—C17B—H17C | 109.2 |
N2A—C17A—H17A | 109.1 | C18B—C17B—H17C | 109.2 |
C18A—C17A—H17A | 109.1 | N2B—C17B—H17D | 109.2 |
N2A—C17A—H17B | 109.1 | C18B—C17B—H17D | 109.2 |
C18A—C17A—H17B | 109.1 | H17C—C17B—H17D | 107.9 |
H17A—C17A—H17B | 107.9 | C17B—C18B—C19B | 110.76 (12) |
C17A—C18A—C19A | 111.11 (12) | C17B—C18B—H18C | 109.5 |
C17A—C18A—H18A | 109.4 | C19B—C18B—H18C | 109.5 |
C19A—C18A—H18A | 109.4 | C17B—C18B—H18D | 109.5 |
C17A—C18A—H18B | 109.4 | C19B—C18B—H18D | 109.5 |
C19A—C18A—H18B | 109.4 | H18C—C18B—H18D | 108.1 |
H18A—C18A—H18B | 108.0 | N3B—C19B—C18B | 111.28 (12) |
N3A—C19A—C18A | 112.24 (12) | N3B—C19B—H19C | 109.4 |
N3A—C19A—H19A | 109.2 | C18B—C19B—H19C | 109.4 |
C18A—C19A—H19A | 109.2 | N3B—C19B—H19D | 109.4 |
N3A—C19A—H19B | 109.2 | C18B—C19B—H19D | 109.4 |
C18A—C19A—H19B | 109.2 | H19C—C19B—H19D | 108.0 |
H19A—C19A—H19B | 107.9 | N3B—C20B—C21B | 103.47 (13) |
N3A—C20A—C21A | 103.17 (13) | N3B—C20B—H20C | 111.1 |
N3A—C20A—H20A | 111.1 | C21B—C20B—H20C | 111.1 |
C21A—C20A—H20A | 111.1 | N3B—C20B—H20D | 111.1 |
N3A—C20A—H20B | 111.1 | C21B—C20B—H20D | 111.1 |
C21A—C20A—H20B | 111.1 | H20C—C20B—H20D | 109.0 |
H20A—C20A—H20B | 109.1 | C22B—C21B—C20B | 103.60 (13) |
C22A—C21A—C20A | 103.56 (14) | C22B—C21B—H21C | 111.0 |
C22A—C21A—H21A | 111.0 | C20B—C21B—H21C | 111.0 |
C20A—C21A—H21A | 111.0 | C22B—C21B—H21D | 111.0 |
C22A—C21A—H21B | 111.0 | C20B—C21B—H21D | 111.0 |
C20A—C21A—H21B | 111.0 | H21C—C21B—H21D | 109.0 |
H21A—C21A—H21B | 109.0 | C23B—C22B—C21B | 104.39 (12) |
C23A—C22A—C21A | 104.34 (12) | C23B—C22B—H22C | 110.9 |
C23A—C22A—H22A | 110.9 | C21B—C22B—H22C | 110.9 |
C21A—C22A—H22A | 110.9 | C23B—C22B—H22D | 110.9 |
C23A—C22A—H22B | 110.9 | C21B—C22B—H22D | 110.9 |
C21A—C22A—H22B | 110.9 | H22C—C22B—H22D | 108.9 |
H22A—C22A—H22B | 108.9 | O3B—C23B—N3B | 124.75 (14) |
O3A—C23A—N3A | 125.12 (14) | O3B—C23B—C22B | 126.85 (13) |
O3A—C23A—C22A | 126.42 (13) | N3B—C23B—C22B | 108.40 (13) |
N3A—C23A—C22A | 108.45 (13) | N4B—C24B—C25B | 111.00 (13) |
N4A—C24A—C25A | 112.80 (14) | N4B—C24B—H24C | 109.4 |
N4A—C24A—H24A | 109.0 | C25B—C24B—H24C | 109.4 |
C25A—C24A—H24A | 109.0 | N4B—C24B—H24D | 109.4 |
N4A—C24A—H24B | 109.0 | C25B—C24B—H24D | 109.4 |
C25A—C24A—H24B | 109.0 | H24C—C24B—H24D | 108.0 |
H24A—C24A—H24B | 107.8 | O4B—C25B—C24B | 111.78 (13) |
O4A—C25A—C24A | 116.21 (15) | O4B—C25B—H25C | 109.3 |
O4A—C25A—H25A | 108.2 | C24B—C25B—H25C | 109.3 |
C24A—C25A—H25A | 108.2 | O4B—C25B—H25D | 109.3 |
O4A—C25A—H25B | 108.2 | C24B—C25B—H25D | 109.3 |
C24A—C25A—H25B | 108.2 | H25C—C25B—H25D | 107.9 |
H25A—C25A—H25B | 107.4 | O4B—C26B—C27B | 110.79 (13) |
O4A—C26A—C27A | 115.26 (15) | O4B—C26B—H26C | 109.5 |
O4A—C26A—H26A | 108.5 | C27B—C26B—H26C | 109.5 |
C27A—C26A—H26A | 108.5 | O4B—C26B—H26D | 109.5 |
O4A—C26A—H26B | 108.5 | C27B—C26B—H26D | 109.5 |
C27A—C26A—H26B | 108.5 | H26C—C26B—H26D | 108.1 |
H26A—C26A—H26B | 107.5 | N4B—C27B—C26B | 110.81 (13) |
N4A—C27A—C26A | 113.01 (14) | N4B—C27B—H27C | 109.5 |
N4A—C27A—H27A | 109.0 | C26B—C27B—H27C | 109.5 |
C26A—C27A—H27A | 109.0 | N4B—C27B—H27D | 109.5 |
N4A—C27A—H27B | 109.0 | C26B—C27B—H27D | 109.5 |
C26A—C27A—H27B | 109.0 | H27C—C27B—H27D | 108.1 |
H27A—C27A—H27B | 107.8 | H1WA—O1WA—H2WA | 103 (2) |
C14B—O1B—C15B | 116.99 (11) | H1WB—O1WB—H2WB | 108 (2) |
C7A—N1A—C1A—C2A | 179.95 (15) | C7B—N1B—C1B—C2B | −179.34 (15) |
C7A—N1A—C1A—C6A | −0.31 (15) | C7B—N1B—C1B—C6B | 0.25 (16) |
N1A—C1A—C2A—C3A | 179.21 (14) | N1B—C1B—C2B—C3B | 179.76 (14) |
C6A—C1A—C2A—C3A | −0.5 (2) | C6B—C1B—C2B—C3B | 0.2 (2) |
C1A—C2A—C3A—C4A | 0.2 (2) | C1B—C2B—C3B—C4B | −0.7 (2) |
C1A—C2A—C3A—C14A | −178.72 (13) | C1B—C2B—C3B—C14B | 179.18 (13) |
C2A—C3A—C4A—C5A | −0.1 (2) | C2B—C3B—C4B—C5B | 0.5 (2) |
C14A—C3A—C4A—C5A | 178.81 (14) | C14B—C3B—C4B—C5B | −179.44 (14) |
C3A—C4A—C5A—C6A | 0.2 (2) | C3B—C4B—C5B—C6B | 0.3 (2) |
C7A—N2A—C6A—C5A | 179.00 (15) | C7B—N2B—C6B—C5B | 178.63 (15) |
C17A—N2A—C6A—C5A | 9.2 (2) | C17B—N2B—C6B—C5B | 7.7 (2) |
C7A—N2A—C6A—C1A | −0.55 (15) | C7B—N2B—C6B—C1B | −0.42 (15) |
C17A—N2A—C6A—C1A | −170.37 (13) | C17B—N2B—C6B—C1B | −171.32 (12) |
C4A—C5A—C6A—N2A | 179.96 (15) | C4B—C5B—C6B—N2B | −179.76 (15) |
C4A—C5A—C6A—C1A | −0.6 (2) | C4B—C5B—C6B—C1B | −0.9 (2) |
N1A—C1A—C6A—N2A | 0.54 (16) | N1B—C1B—C6B—N2B | 0.12 (16) |
C2A—C1A—C6A—N2A | −179.68 (13) | C2B—C1B—C6B—N2B | 179.75 (13) |
N1A—C1A—C6A—C5A | −179.05 (13) | N1B—C1B—C6B—C5B | −179.03 (13) |
C2A—C1A—C6A—C5A | 0.7 (2) | C2B—C1B—C6B—C5B | 0.6 (2) |
C1A—N1A—C7A—N2A | −0.05 (16) | C1B—N1B—C7B—N2B | −0.53 (16) |
C1A—N1A—C7A—C8A | 178.61 (12) | C1B—N1B—C7B—C8B | 179.32 (13) |
C6A—N2A—C7A—N1A | 0.39 (16) | C6B—N2B—C7B—N1B | 0.62 (16) |
C17A—N2A—C7A—N1A | 169.69 (13) | C17B—N2B—C7B—N1B | 171.07 (13) |
C6A—N2A—C7A—C8A | −178.23 (13) | C6B—N2B—C7B—C8B | −179.23 (13) |
C17A—N2A—C7A—C8A | −8.9 (2) | C17B—N2B—C7B—C8B | −8.8 (2) |
N1A—C7A—C8A—C9A | 141.68 (15) | N1B—C7B—C8B—C9B | 133.39 (15) |
N2A—C7A—C8A—C9A | −39.8 (2) | N2B—C7B—C8B—C9B | −46.8 (2) |
N1A—C7A—C8A—C13A | −35.0 (2) | N1B—C7B—C8B—C13B | −43.5 (2) |
N2A—C7A—C8A—C13A | 143.50 (14) | N2B—C7B—C8B—C13B | 136.29 (14) |
C13A—C8A—C9A—C10A | −1.5 (2) | C13B—C8B—C9B—C10B | 0.3 (2) |
C7A—C8A—C9A—C10A | −178.16 (13) | C7B—C8B—C9B—C10B | −176.69 (13) |
C8A—C9A—C10A—C11A | 0.1 (2) | C8B—C9B—C10B—C11B | −1.0 (2) |
C24A—N4A—C11A—C12A | −170.35 (15) | C9B—C10B—C11B—N4B | 178.81 (13) |
C27A—N4A—C11A—C12A | 45.7 (2) | C9B—C10B—C11B—C12B | 0.7 (2) |
C24A—N4A—C11A—C10A | 7.4 (2) | C24B—N4B—C11B—C10B | 11.1 (2) |
C27A—N4A—C11A—C10A | −136.52 (16) | C27B—N4B—C11B—C10B | 145.42 (14) |
C9A—C10A—C11A—N4A | −176.83 (14) | C24B—N4B—C11B—C12B | −170.82 (14) |
C9A—C10A—C11A—C12A | 1.0 (2) | C27B—N4B—C11B—C12B | −36.54 (19) |
N4A—C11A—C12A—C13A | 177.14 (14) | C10B—C11B—C12B—C13B | 0.2 (2) |
C10A—C11A—C12A—C13A | −0.8 (2) | N4B—C11B—C12B—C13B | −177.93 (13) |
C11A—C12A—C13A—C8A | −0.6 (2) | C11B—C12B—C13B—C8B | −0.9 (2) |
C9A—C8A—C13A—C12A | 1.7 (2) | C9B—C8B—C13B—C12B | 0.6 (2) |
C7A—C8A—C13A—C12A | 178.62 (13) | C7B—C8B—C13B—C12B | 177.74 (13) |
C15A—O1A—C14A—O2A | −1.4 (2) | C15B—O1B—C14B—O2B | −1.9 (2) |
C15A—O1A—C14A—C3A | 179.14 (13) | C15B—O1B—C14B—C3B | 176.96 (12) |
C2A—C3A—C14A—O2A | 3.4 (2) | C2B—C3B—C14B—O2B | 8.8 (2) |
C4A—C3A—C14A—O2A | −175.51 (15) | C4B—C3B—C14B—O2B | −171.27 (15) |
C2A—C3A—C14A—O1A | −177.09 (12) | C2B—C3B—C14B—O1B | −170.03 (13) |
C4A—C3A—C14A—O1A | 4.0 (2) | C4B—C3B—C14B—O1B | 9.9 (2) |
C14A—O1A—C15A—C16A | −172.75 (14) | C14B—O1B—C15B—C16B | −162.12 (15) |
C6A—N2A—C17A—C18A | 85.14 (17) | C6B—N2B—C17B—C18B | 74.78 (17) |
C7A—N2A—C17A—C18A | −82.40 (17) | C7B—N2B—C17B—C18B | −94.10 (17) |
N2A—C17A—C18A—C19A | 168.93 (12) | N2B—C17B—C18B—C19B | 163.07 (12) |
C23A—N3A—C19A—C18A | 94.52 (17) | C23B—N3B—C19B—C18B | 100.16 (16) |
C20A—N3A—C19A—C18A | −91.63 (17) | C20B—N3B—C19B—C18B | −81.86 (17) |
C17A—C18A—C19A—N3A | −76.53 (16) | C17B—C18B—C19B—N3B | −66.92 (17) |
C23A—N3A—C20A—C21A | −17.48 (18) | C23B—N3B—C20B—C21B | −16.40 (17) |
C19A—N3A—C20A—C21A | 168.04 (14) | C19B—N3B—C20B—C21B | 165.41 (13) |
N3A—C20A—C21A—C22A | 24.94 (18) | N3B—C20B—C21B—C22B | 24.60 (16) |
C20A—C21A—C22A—C23A | −24.16 (18) | C20B—C21B—C22B—C23B | −24.49 (16) |
C19A—N3A—C23A—O3A | −3.0 (2) | C19B—N3B—C23B—O3B | −0.6 (2) |
C20A—N3A—C23A—O3A | −177.29 (15) | C20B—N3B—C23B—O3B | −178.71 (14) |
C19A—N3A—C23A—C22A | 176.23 (13) | C19B—N3B—C23B—C22B | 178.76 (12) |
C20A—N3A—C23A—C22A | 1.95 (18) | C20B—N3B—C23B—C22B | 0.63 (17) |
C21A—C22A—C23A—O3A | −166.17 (15) | C21B—C22B—C23B—O3B | −165.12 (14) |
C21A—C22A—C23A—N3A | 14.59 (17) | C21B—C22B—C23B—N3B | 15.55 (16) |
C11A—N4A—C24A—C25A | 170.14 (16) | C11B—N4B—C24B—C25B | −170.75 (13) |
C27A—N4A—C24A—C25A | −44.7 (2) | C27B—N4B—C24B—C25B | 52.27 (17) |
C26A—O4A—C25A—C24A | −46.8 (3) | C26B—O4B—C25B—C24B | 59.34 (17) |
N4A—C24A—C25A—O4A | 45.7 (3) | N4B—C24B—C25B—O4B | −55.84 (18) |
C25A—O4A—C26A—C27A | 47.3 (2) | C25B—O4B—C26B—C27B | −60.60 (17) |
C11A—N4A—C27A—C26A | −168.58 (15) | C11B—N4B—C27B—C26B | 168.84 (13) |
C24A—N4A—C27A—C26A | 45.7 (2) | C24B—N4B—C27B—C26B | −53.93 (17) |
O4A—C26A—C27A—N4A | −47.1 (2) | O4B—C26B—C27B—N4B | 58.54 (18) |
Cg1, Cg2, Cg3 and Cg4 are the centroids of the N1A/N2A/C1A/C6A/C7A, C21B–C26B, C21A–C26A and C21B–C26B rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C17A—H17B···O3A | 0.99 | 2.50 | 3.2624 (18) | 133 |
O1WA—H1WA···O3Bi | 0.88 (3) | 2.00 (3) | 2.8652 (18) | 168 (2) |
O1WA—H2WA···N1Bii | 0.91 (3) | 2.01 (3) | 2.9142 (18) | 172 (2) |
O1WB—H1WB···N1A | 0.87 (3) | 2.05 (3) | 2.9142 (19) | 172 (2) |
O1WB—H2WB···O3Aiii | 0.83 (3) | 1.99 (3) | 2.8218 (18) | 174 (2) |
C15A—H15B···O2Biv | 0.99 | 2.59 | 3.412 (2) | 141 |
C15B—H15D···O2Aiv | 0.99 | 2.50 | 3.227 (2) | 130 |
C17A—H17A···O3Bi | 0.99 | 2.44 | 3.4334 (18) | 178 |
C17B—H17C···O3Ai | 0.99 | 2.36 | 3.3274 (18) | 166 |
C25A—H25A···O2Bv | 0.99 | 2.37 | 3.309 (2) | 159 |
C26A—H26B···O4Bvi | 0.99 | 2.54 | 3.425 (2) | 148 |
C13B—H13B···Cg1iii | 0.95 | 2.87 | 3.5419 (15) | 129 |
C21B—H21D···Cg2 | 0.99 | 2.96 | 3.8494 (18) | 150 |
C24A—H24B···Cg3iii | 0.99 | 2.79 | 3.7712 (19) | 172 |
C24B—H24D···Cg4vii | 0.99 | 2.67 | 3.6357 (17) | 165 |
Symmetry codes: (i) −x, −y+1, −z; (ii) x, y+1, z; (iii) −x+1, −y+1, −z; (iv) −x+1, −y+1, −z+1; (v) x, y, z−1; (vi) −x+1, −y, −z−1; (vii) −x, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C27H32N4O4·H2O |
Mr | 494.58 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 12.2602 (3), 13.7267 (4), 15.3163 (4) |
α, β, γ (°) | 99.357 (1), 93.700 (1), 94.003 (1) |
V (Å3) | 2529.56 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.67 × 0.40 × 0.11 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.942, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 61724, 14611, 10995 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.152, 1.03 |
No. of reflections | 14611 |
No. of parameters | 667 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.58, −0.37 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
Cg1, Cg2, Cg3 and Cg4 are the centroids of the N1A/N2A/C1A/C6A/C7A, C21B–C26B, C21A–C26A and C21B–C26B rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C17A—H17B···O3A | 0.99 | 2.50 | 3.2624 (18) | 133 |
O1WA—H1WA···O3Bi | 0.88 (3) | 2.00 (3) | 2.8652 (18) | 168 (2) |
O1WA—H2WA···N1Bii | 0.91 (3) | 2.01 (3) | 2.9142 (18) | 172 (2) |
O1WB—H1WB···N1A | 0.87 (3) | 2.05 (3) | 2.9142 (19) | 172 (2) |
O1WB—H2WB···O3Aiii | 0.83 (3) | 1.99 (3) | 2.8218 (18) | 174 (2) |
C15A—H15B···O2Biv | 0.99 | 2.59 | 3.412 (2) | 141 |
C15B—H15D···O2Aiv | 0.99 | 2.50 | 3.227 (2) | 130 |
C17A—H17A···O3Bi | 0.99 | 2.44 | 3.4334 (18) | 178 |
C17B—H17C···O3Ai | 0.99 | 2.36 | 3.3274 (18) | 166 |
C25A—H25A···O2Bv | 0.99 | 2.37 | 3.309 (2) | 159 |
C26A—H26B···O4Bvi | 0.99 | 2.54 | 3.425 (2) | 148 |
C13B—H13B···Cg1iii | 0.95 | 2.87 | 3.5419 (15) | 129 |
C21B—H21D···Cg2 | 0.99 | 2.96 | 3.8494 (18) | 150 |
C24A—H24B···Cg3iii | 0.99 | 2.79 | 3.7712 (19) | 172 |
C24B—H24D···Cg4vii | 0.99 | 2.67 | 3.6357 (17) | 165 |
Symmetry codes: (i) −x, −y+1, −z; (ii) x, y+1, z; (iii) −x+1, −y+1, −z; (iv) −x+1, −y+1, −z+1; (v) x, y, z−1; (vi) −x+1, −y, −z−1; (vii) −x, −y, −z. |
Acknowledgements
The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research University grants (Nos. 1001/PFIZIK/811151 and 1001/PSK/8620012) and HiCoE research grant (No. 311.CIPPM.4401005). They also wish to express their thanks to the Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Molecular Medicine, Universiti Sains Malaysia for supporting this work. SA thanks the Malaysian Government and USM for an Academic Staff Training Scheme (ASTS) fellowship.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Benzimidazoles belong to one of the well known and most extensively studied class of compounds due to their biological activities such as anti-cancer (Townsend & Revankar, 1970) and anthelmintics (Dubey & Sanyal, 2010). As part of our ongoing structural studies of benzimidazole derivatives (Yoon, Ali, Wei et al. 2011), we report herein the crystal structure of the title compound.
The asymmetric unit of the title compound, (Fig. 1), consists of two crystallographically independent (A and B) Ethyl 2-(4-morpholinophenyl)-1-(3-oxopyrolidin-1-yl) propyl)-1H-benzo [d]imidazole-5-carboxylate and two water molecules. In both molecules, the pyrrolidine rings (N3A/C20A–C23A & N3B/C20B–C23B) are in envelope conformations (Cremer & Pople, 1975) with puckering parameters, Q= 0.2575 (19) Å and φ= 69.4 (4)° in which C21A is the flap and Q= 0.2563 (17) Å and φ= 71.7 (4)° in which C21B is the flap. The morpholine rings, O4A/N4A/C24A–C27A [puckering paramaters; Q = 0.4341 (18) Å, Θ= 1.1 (3)° and φ= 256 (10)°] and O4B/N4B/C24B–C27B [puckering paramaters; Q = 0.5605 (16) Å, Θ= 176.18 (16)° and φ= 153 (3)°] adopt chair conformations. The benzimidazole rings (N1A/N2A/C1A–C7A and N1B/N2B/C1B–C7B) are essentially planar with maximum deviation of 0.008 (1) Å at atom N2A, C6B and C7B. In molecule A, the benzimidazole ring, N1A/N2A/C1A–C7A, forms a dihedral of 37.65 (6)° with the benzene (C8A–C13A) ring. The corresponding dihedral angle in molecule B is 45.44 (6)°. In molecule B, an intramolecular C17A—H17B···O3A hydrogen bond (Table 1) forms S(7) ring motif (Bernstein et al., 1995). The bond lengths and angles are within normal ranges and comparable to the related structures (Yoon, Ali, Wei et al., 2011; Yoon et al., 2012; Yoon, Ali, Choon et al., 2011).
In the crystal packing (Fig. 2), intermolecular O—H···O, C—H···N and C—H···O hydrogen bonds (Table 1) link the molecules into a three-dimensional network. The intermolecular C13B—H13B···Cg1iii, C21B—H21D···Cg2, C24A—H24B···Cg3iii and C24B—H24D···Cg4vii (Table 1) interactions further stabilize the crystal structure (Cg1, Cg2, Cg3 and Cg4 are the centroids of N1A/N2A/C1A/C6A/C7A, C21B–C26B, C21A–C26A and C21B–C26B rings, respectively).