#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/75/2227546.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227546
loop_
_publ_author_name
'Prasath, R.'
'Sarveswari, S.'
'Vijayakumar, V.'
'Ng, Seik Weng'
'Tiekink, Edward R. T.'
_publ_section_title
;
 (2E)-3-(4-Methylphenyl)-1-(2-methyl-4-phenylquinolin-3-yl)prop-2-en-1-one
 monohydrate
;
_journal_coeditor_code           HB5655
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2710
_journal_page_last               o2711
_journal_paper_doi               10.1107/S1600536810038791
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C26 H21 N O, H2 O'
_chemical_formula_moiety         'C26 H21 N O, H2 O'
_chemical_formula_sum            'C26 H23 N O2'
_chemical_formula_weight         381.45
_chemical_name_systematic
;
(2E)-3-(4-Methylphenyl)-1-(2-methyl-4-phenylquinolin-3-yl)prop-2-en-1-one
monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.1370(10)
_cell_angle_beta                 101.5370(10)
_cell_angle_gamma                100.8200(10)
_cell_formula_units_Z            2
_cell_length_a                   8.2634(7)
_cell_length_b                   9.0785(7)
_cell_length_c                   14.1176(12)
_cell_measurement_reflns_used    4003
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.3
_cell_volume                     1017.43(15)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_av_sigmaI/netI    0.034
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9738
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.3
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.01
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4647
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.01
_refine_ls_R_factor_all          0.057
_refine_ls_R_factor_gt           0.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1041P)²+0.3702P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.141
_refine_ls_wR_factor_ref         0.165
_reflns_number_gt                3790
_reflns_number_total             4647
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5655.cif
_cod_data_source_block           I
_cod_database_code               2227546
_cod_database_fobs_code          2227546
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.94050(14) 0.59600(13) 0.73474(8) 0.0254(3) Uani d . 1 . .
O O1W 1.28132(15) 0.67478(13) 0.84124(8) 0.0250(3) Uani d D 1 . .
H H1W 1.1758(13) 0.660(2) 0.8172(15) 0.037 Uiso d D 1 . .
H H2W 1.280(3) 0.623(2) 0.8910(11) 0.037 Uiso d D 1 . .
N N1 0.74421(16) 0.53267(14) 1.00612(9) 0.0196(3) Uani d . 1 . .
C C1 0.71971(18) 0.67293(16) 1.03036(10) 0.0177(3) Uani d . 1 . .
C C2 0.6977(2) 0.70135(18) 1.12519(11) 0.0224(3) Uani d . 1 . .
H H2 0.6987 0.6239 1.1695 0.027 Uiso calc R 1 . .
C C3 0.6751(2) 0.83978(18) 1.15372(11) 0.0232(3) Uani d . 1 . .
H H3 0.6601 0.8577 1.2176 0.028 Uiso calc R 1 . .
C C4 0.67398(19) 0.95613(17) 1.08882(11) 0.0227(3) Uani d . 1 . .
H H4 0.6585 1.0519 1.1092 0.027 Uiso calc R 1 . .
C C5 0.69517(19) 0.93110(17) 0.99649(11) 0.0196(3) Uani d . 1 . .
H H5 0.6947 1.0101 0.9533 0.024 Uiso calc R 1 . .
C C6 0.71780(17) 0.78851(16) 0.96457(10) 0.0169(3) Uani d . 1 . .
C C7 0.73952(17) 0.75512(16) 0.86916(10) 0.0166(3) Uani d . 1 . .
C C8 0.76569(18) 0.61495(16) 0.84716(10) 0.0169(3) Uani d . 1 . .
C C9 0.76789(18) 0.50488(17) 0.91867(11) 0.0190(3) Uani d . 1 . .
C C10 0.8000(2) 0.35126(17) 0.89604(12) 0.0245(3) Uani d . 1 . .
H H10A 0.8047 0.2937 0.9542 0.037 Uiso calc R 1 . .
H H10B 0.9073 0.3616 0.8749 0.037 Uiso calc R 1 . .
H H10C 0.7087 0.2987 0.8443 0.037 Uiso calc R 1 . .
C C11 0.73297(18) 0.87247(16) 0.79625(10) 0.0173(3) Uani d . 1 . .
C C12 0.88036(19) 0.96807(17) 0.78550(11) 0.0214(3) Uani d . 1 . .
H H12 0.9857 0.9572 0.8235 0.026 Uiso calc R 1 . .
C C13 0.8738(2) 1.07962(17) 0.71923(12) 0.0232(3) Uani d . 1 . .
H H13 0.9745 1.1449 0.7123 0.028 Uiso calc R 1 . .
C C14 0.7202(2) 1.09540(17) 0.66338(11) 0.0218(3) Uani d . 1 . .
H H14 0.7157 1.1709 0.6178 0.026 Uiso calc R 1 . .
C C15 0.5731(2) 1.00064(17) 0.67422(11) 0.0225(3) Uani d . 1 . .
H H15 0.4680 1.0117 0.6360 0.027 Uiso calc R 1 . .
C C16 0.57866(19) 0.88978(17) 0.74058(11) 0.0197(3) Uani d . 1 . .
H H16 0.4775 0.8258 0.7481 0.024 Uiso calc R 1 . .
C C17 0.79675(18) 0.57226(16) 0.74902(11) 0.0179(3) Uani d . 1 . .
C C18 0.65484(19) 0.49748(16) 0.67431(10) 0.0189(3) Uani d . 1 . .
H H18 0.6776 0.4576 0.6167 0.023 Uiso calc R 1 . .
C C19 0.49390(19) 0.48223(16) 0.68281(10) 0.0181(3) Uani d . 1 . .
H H19 0.4744 0.5264 0.7400 0.022 Uiso calc R 1 . .
C C20 0.34572(18) 0.40472(16) 0.61317(10) 0.0177(3) Uani d . 1 . .
C C21 0.18670(19) 0.42552(17) 0.62322(11) 0.0203(3) Uani d . 1 . .
H H21 0.1774 0.4912 0.6742 0.024 Uiso calc R 1 . .
C C22 0.04245(19) 0.35188(17) 0.56003(11) 0.0215(3) Uani d . 1 . .
H H22 -0.0642 0.3687 0.5680 0.026 Uiso calc R 1 . .
C C23 0.0509(2) 0.25349(17) 0.48501(11) 0.0221(3) Uani d . 1 . .
C C24 0.2101(2) 0.23307(18) 0.47450(11) 0.0227(3) Uani d . 1 . .
H H24 0.2189 0.1672 0.4235 0.027 Uiso calc R 1 . .
C C25 0.3546(2) 0.30677(17) 0.53679(11) 0.0216(3) Uani d . 1 . .
H H25 0.4613 0.2912 0.5280 0.026 Uiso calc R 1 . .
C C26 -0.1064(2) 0.1710(2) 0.41757(12) 0.0291(4) Uani d . 1 . .
H H26A -0.2011 0.2191 0.4232 0.044 Uiso calc R 1 . .
H H26B -0.1308 0.0663 0.4348 0.044 Uiso calc R 1 . .
H H26C -0.0898 0.1740 0.3508 0.044 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
H1W O1W H2W . . 100(2) ?
C9 N1 C1 . . 118.81(13) ?
N1 C1 C2 . . 117.92(13) ?
N1 C1 C6 . . 122.51(13) ?
C2 C1 C6 . . 119.57(13) ?
C3 C2 C1 . . 120.42(15) ?
C3 C2 H2 . . 119.8 ?
C1 C2 H2 . . 119.8 ?
C2 C3 C4 . . 120.46(14) ?
C2 C3 H3 . . 119.8 ?
C4 C3 H3 . . 119.8 ?
C5 C4 C3 . . 120.12(14) ?
C5 C4 H4 . . 119.9 ?
C3 C4 H4 . . 119.9 ?
C4 C5 C6 . . 120.74(14) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C1 C6 C5 . . 118.69(13) ?
C1 C6 C7 . . 117.89(13) ?
C5 C6 C7 . . 123.41(13) ?
C8 C7 C6 . . 118.43(13) ?
C8 C7 C11 . . 121.85(13) ?
C6 C7 C11 . . 119.71(12) ?
C7 C8 C9 . . 120.04(13) ?
C7 C8 C17 . . 121.83(13) ?
C9 C8 C17 . . 118.12(12) ?
N1 C9 C8 . . 122.29(13) ?
N1 C9 C10 . . 117.14(13) ?
C8 C9 C10 . . 120.57(13) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C12 C11 C16 . . 119.54(14) ?
C12 C11 C7 . . 120.23(13) ?
C16 C11 C7 . . 120.21(13) ?
C11 C12 C13 . . 120.23(14) ?
C11 C12 H12 . . 119.9 ?
C13 C12 H12 . . 119.9 ?
C14 C13 C12 . . 120.00(14) ?
C14 C13 H13 . . 120.0 ?
C12 C13 H13 . . 120.0 ?
C13 C14 C15 . . 119.89(14) ?
C13 C14 H14 . . 120.1 ?
C15 C14 H14 . . 120.1 ?
C14 C15 C16 . . 120.39(14) ?
C14 C15 H15 . . 119.8 ?
C16 C15 H15 . . 119.8 ?
C15 C16 C11 . . 119.95(14) ?
C15 C16 H16 . . 120.0 ?
C11 C16 H16 . . 120.0 ?
O1 C17 C18 . . 121.12(13) ?
O1 C17 C8 . . 119.76(13) ?
C18 C17 C8 . . 119.07(12) ?
C19 C18 C17 . . 123.29(13) ?
C19 C18 H18 . . 118.4 ?
C17 C18 H18 . . 118.4 ?
C18 C19 C20 . . 126.63(13) ?
C18 C19 H19 . . 116.7 ?
C20 C19 H19 . . 116.7 ?
C21 C20 C25 . . 117.89(14) ?
C21 C20 C19 . . 119.03(13) ?
C25 C20 C19 . . 123.06(13) ?
C22 C21 C20 . . 121.01(13) ?
C22 C21 H21 . . 119.5 ?
C20 C21 H21 . . 119.5 ?
C21 C22 C23 . . 121.16(14) ?
C21 C22 H22 . . 119.4 ?
C23 C22 H22 . . 119.4 ?
C22 C23 C24 . . 117.93(14) ?
C22 C23 C26 . . 121.08(14) ?
C24 C23 C26 . . 120.99(14) ?
C25 C24 C23 . . 121.28(14) ?
C25 C24 H24 . . 119.4 ?
C23 C24 H24 . . 119.4 ?
C24 C25 C20 . . 120.72(14) ?
C24 C25 H25 . . 119.6 ?
C20 C25 H25 . . 119.6 ?
C23 C26 H26A . . 109.5 ?
C23 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C23 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C17 . 1.2245(18) ?
O1W H1W . 0.854(10) ?
O1W H2W . 0.852(9) ?
N1 C9 . 1.3149(19) ?
N1 C1 . 1.3736(18) ?
C1 C2 . 1.412(2) ?
C1 C6 . 1.415(2) ?
C2 C3 . 1.369(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.412(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.370(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.4196(19) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.428(2) ?
C7 C8 . 1.370(2) ?
C7 C11 . 1.497(2) ?
C8 C9 . 1.434(2) ?
C8 C17 . 1.5146(19) ?
C9 C10 . 1.507(2) ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 C12 . 1.394(2) ?
C11 C16 . 1.396(2) ?
C12 C13 . 1.394(2) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.388(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.389(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.389(2) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C17 C18 . 1.458(2) ?
C18 C19 . 1.341(2) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.459(2) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.396(2) ?
C20 C25 . 1.406(2) ?
C21 C22 . 1.384(2) ?
C21 H21 . 0.9500 ?
C22 C23 . 1.393(2) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.398(2) ?
C23 C26 . 1.506(2) ?
C24 C25 . 1.380(2) ?
C24 H24 . 0.9500 ?
C25 H25 . 0.9500 ?
C26 H26A . 0.9800 ?
C26 H26B . 0.9800 ?
C26 H26C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1w H1w O1 . 0.854(10) 2.029(11) 2.8654(17) 166(2)
O1w H2w N1 2_767 0.852(9) 2.061(10) 2.9032(17) 170(2)
C4 H4 O1w 2_777 0.95 2.49 3.4055(19) 161
C16 H16 O1w 1_455 0.95 2.52 3.402(2) 155
C24 H24 Cg1 2_666 0.95 2.70 3.6414(17) 171
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N1 C1 C2 . . . . -178.81(14) ?
C9 N1 C1 C6 . . . . 0.4(2) ?
N1 C1 C2 C3 . . . . 179.12(14) ?
C6 C1 C2 C3 . . . . -0.2(2) ?
C1 C2 C3 C4 . . . . -0.2(2) ?
C2 C3 C4 C5 . . . . 0.2(2) ?
C3 C4 C5 C6 . . . . 0.3(2) ?
N1 C1 C6 C5 . . . . -178.69(13) ?
C2 C1 C6 C5 . . . . 0.6(2) ?
N1 C1 C6 C7 . . . . 1.1(2) ?
C2 C1 C6 C7 . . . . -179.66(13) ?
C4 C5 C6 C1 . . . . -0.6(2) ?
C4 C5 C6 C7 . . . . 179.62(14) ?
C1 C6 C7 C8 . . . . -1.8(2) ?
C5 C6 C7 C8 . . . . 177.97(13) ?
C1 C6 C7 C11 . . . . 178.09(13) ?
C5 C6 C7 C11 . . . . -2.1(2) ?
C6 C7 C8 C9 . . . . 1.1(2) ?
C11 C7 C8 C9 . . . . -178.82(13) ?
C6 C7 C8 C17 . . . . -177.54(13) ?
C11 C7 C8 C17 . . . . 2.6(2) ?
C1 N1 C9 C8 . . . . -1.3(2) ?
C1 N1 C9 C10 . . . . 178.05(13) ?
C7 C8 C9 N1 . . . . 0.5(2) ?
C17 C8 C9 N1 . . . . 179.17(13) ?
C7 C8 C9 C10 . . . . -178.78(14) ?
C17 C8 C9 C10 . . . . -0.1(2) ?
C8 C7 C11 C12 . . . . -87.84(18) ?
C6 C7 C11 C12 . . . . 92.27(17) ?
C8 C7 C11 C16 . . . . 94.05(17) ?
C6 C7 C11 C16 . . . . -85.84(17) ?
C16 C11 C12 C13 . . . . -0.4(2) ?
C7 C11 C12 C13 . . . . -178.49(13) ?
C11 C12 C13 C14 . . . . -0.3(2) ?
C12 C13 C14 C15 . . . . 0.5(2) ?
C13 C14 C15 C16 . . . . -0.1(2) ?
C14 C15 C16 C11 . . . . -0.5(2) ?
C12 C11 C16 C15 . . . . 0.7(2) ?
C7 C11 C16 C15 . . . . 178.87(13) ?
C7 C8 C17 O1 . . . . 88.14(18) ?
C9 C8 C17 O1 . . . . -90.49(17) ?
C7 C8 C17 C18 . . . . -94.46(17) ?
C9 C8 C17 C18 . . . . 86.91(17) ?
O1 C17 C18 C19 . . . . -173.19(14) ?
C8 C17 C18 C19 . . . . 9.4(2) ?
C17 C18 C19 C20 . . . . -177.71(13) ?
C18 C19 C20 C21 . . . . -166.79(15) ?
C18 C19 C20 C25 . . . . 14.5(2) ?
C25 C20 C21 C22 . . . . 0.1(2) ?
C19 C20 C21 C22 . . . . -178.68(13) ?
C20 C21 C22 C23 . . . . 0.7(2) ?
C21 C22 C23 C24 . . . . -1.0(2) ?
C21 C22 C23 C26 . . . . 178.73(14) ?
C22 C23 C24 C25 . . . . 0.6(2) ?
C26 C23 C24 C25 . . . . -179.16(15) ?
C23 C24 C25 C20 . . . . 0.2(2) ?
C21 C20 C25 C24 . . . . -0.5(2) ?
C19 C20 C25 C24 . . . . 178.20(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656238
