#------------------------------------------------------------------------------
#$Date: 2020-08-14 07:44:27 +0300 (Fri, 14 Aug 2020) $
#$Revision: 255314 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/22/2022231.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022231
loop_
_publ_author_name
'Rodríguez, Diego'
'Guerrero, Sergio Andrés'
'Palma, Alirio'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 4-Styrylquinolines from cyclocondensation reactions between
 (2-aminophenyl)chalcones and 1,3-diketones: crystal structures and
 regiochemistry
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229620010803
_journal_volume                  76
_journal_year                    2020
_chemical_formula_moiety         'C26 H21 N O'
_chemical_formula_sum            'C26 H21 N O'
_chemical_formula_weight         363.44
_chemical_name_systematic
;
(E)-3-benzoyl-2-methyl-4-(3-methylstyryl)quinoline
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.2730(16)
_cell_length_b                   14.8012(16)
_cell_length_c                   20.137(2)
_cell_measurement_reflns_used    4914
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.328
_cell_measurement_theta_min      2.296
_cell_volume                     3956.0(8)
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2016.7-2 (Bruker, 2018)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2020)'
_computing_publication_material
'SHELXL-2014 (Sheldrick, 2015b) and PLATON (Spek, 2020)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1421
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            58957
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.328
_diffrn_reflns_theta_min         2.296
_diffrn_source
'INCOATEC high brilliance microfocus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2 (Bruker, 2016)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       plate
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.303
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.303
_refine_ls_R_factor_all          0.1440
_refine_ls_R_factor_gt           0.1172
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0269P)²+9.6832P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1909
_refine_ls_wR_factor_ref         0.2005
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3892
_reflns_number_total             4914
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sk3755sup14.cif
_cod_data_source_block           VII
_cod_original_cell_volume        3956.1(8)
_cod_database_code               2022231
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.992
_shelx_estimated_absorpt_t_max   0.997
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7612(2) 0.3408(2) 0.42050(14) 0.0203(6) Uani 1 1 d . . . . .
C2 C 0.7855(3) 0.3422(2) 0.35715(16) 0.0197(7) Uani 1 1 d . . . . .
C3 C 0.7200(2) 0.3067(2) 0.30658(15) 0.0168(7) Uani 1 1 d . . . . .
C4 C 0.6288(2) 0.2686(2) 0.32371(15) 0.0155(6) Uani 1 1 d . . . . .
C4A C 0.5997(2) 0.2696(2) 0.39225(15) 0.0167(7) Uani 1 1 d . . . . .
C5 C 0.5065(3) 0.2356(2) 0.41546(17) 0.0219(7) Uani 1 1 d . . . . .
H5 H 0.4591 0.2118 0.3848 0.026 Uiso 1 1 calc R U . . .
C6 C 0.4838(3) 0.2369(3) 0.48224(17) 0.0253(8) Uani 1 1 d . . . . .
H6 H 0.4211 0.2141 0.4975 0.030 Uiso 1 1 calc R U . . .
C7 C 0.5542(3) 0.2721(3) 0.52767(17) 0.0273(8) Uani 1 1 d . . . . .
H7 H 0.5385 0.2725 0.5737 0.033 Uiso 1 1 calc R U . . .
C8 C 0.6444(3) 0.3055(2) 0.50684(16) 0.0238(8) Uani 1 1 d . . . . .
H8 H 0.6907 0.3291 0.5384 0.029 Uiso 1 1 calc R U . . .
C8A C 0.6698(3) 0.3053(2) 0.43836(16) 0.0205(7) Uani 1 1 d . . . . .
C21 C 0.8845(3) 0.3843(3) 0.33903(18) 0.0281(8) Uani 1 1 d . . . . .
H21A H 0.9301 0.3376 0.3221 0.042 Uiso 1 1 calc R U . . .
H21B H 0.9142 0.4126 0.3784 0.042 Uiso 1 1 calc R U . . .
H21C H 0.8738 0.4302 0.3047 0.042 Uiso 1 1 calc R U . . .
C31 C 0.7529(3) 0.3111(2) 0.23478(15) 0.0179(7) Uani 1 1 d . . . . .
O31 O 0.82027(18) 0.26244(17) 0.21495(11) 0.0234(6) Uani 1 1 d . . . . .
C311 C 0.7029(2) 0.3778(2) 0.19032(15) 0.0168(7) Uani 1 1 d . . . . .
C312 C 0.6452(3) 0.4490(2) 0.21499(16) 0.0199(7) Uani 1 1 d . . . . .
H312 H 0.6332 0.4538 0.2614 0.024 Uiso 1 1 calc R U . . .
C313 C 0.6056(3) 0.5125(3) 0.17198(17) 0.0231(8) Uani 1 1 d . . . . .
H313 H 0.5680 0.5619 0.1890 0.028 Uiso 1 1 calc R U . . .
C314 C 0.6204(3) 0.5044(3) 0.10399(18) 0.0273(8) Uani 1 1 d . . . . .
H314 H 0.5927 0.5480 0.0745 0.033 Uiso 1 1 calc R U . . .
C315 C 0.6759(3) 0.4323(3) 0.07942(17) 0.0267(8) Uani 1 1 d . . . . .
H315 H 0.6850 0.4259 0.0329 0.032 Uiso 1 1 calc R U . . .
C316 C 0.7179(3) 0.3701(2) 0.12185(16) 0.0221(7) Uani 1 1 d . . . . .
H316 H 0.7572 0.3218 0.1046 0.026 Uiso 1 1 calc R U . . .
C41 C 0.5644(3) 0.2231(2) 0.27401(14) 0.0164(6) Uani 1 1 d . . . . .
H41 H 0.4954 0.2398 0.2709 0.020 Uiso 1 1 calc R U . . .
C42 C 0.6000(3) 0.1596(2) 0.23349(15) 0.0176(7) Uani 1 1 d . . . . .
H42 H 0.6699 0.1466 0.2371 0.021 Uiso 1 1 calc R U . . .
C421 C 0.5434(3) 0.1070(2) 0.18365(14) 0.0166(7) Uani 1 1 d . . . . .
C422 C 0.4415(3) 0.1201(2) 0.17108(15) 0.0179(7) Uani 1 1 d . . . . .
H422 H 0.4051 0.1631 0.1965 0.021 Uiso 1 1 calc R U . . .
C423 C 0.3916(3) 0.0712(2) 0.12191(16) 0.0197(7) Uani 1 1 d . . . . .
C424 C 0.4460(3) 0.0072(2) 0.08595(17) 0.0243(8) Uani 1 1 d . . . . .
H424 H 0.4134 -0.0264 0.0520 0.029 Uiso 1 1 calc R U . . .
C425 C 0.5466(3) -0.0080(2) 0.09912(17) 0.0260(8) Uani 1 1 d . . . . .
H425 H 0.5823 -0.0527 0.0748 0.031 Uiso 1 1 calc R U . . .
C426 C 0.5959(3) 0.0415(2) 0.14752(17) 0.0228(7) Uani 1 1 d . . . . .
H426 H 0.6653 0.0310 0.1562 0.027 Uiso 1 1 calc R U . . .
C427 C 0.2819(3) 0.0870(3) 0.10719(19) 0.0293(9) Uani 1 1 d . . . . .
H42A H 0.2537 0.0337 0.0852 0.044 Uiso 1 1 calc R U . . .
H42B H 0.2749 0.1396 0.0780 0.044 Uiso 1 1 calc R U . . .
H42C H 0.2456 0.0980 0.1488 0.044 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C8A 118.5(3) . . ?
N1 C2 C3 122.2(3) . . ?
N1 C2 C21 117.2(3) . . ?
C3 C2 C21 120.6(3) . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 C31 120.7(3) . . ?
C2 C3 C31 119.2(3) . . ?
C3 C4 C4A 118.2(3) . . ?
C3 C4 C41 121.6(3) . . ?
C4A C4 C41 120.0(3) . . ?
C5 C4A C8A 119.4(3) . . ?
C5 C4A C4 123.4(3) . . ?
C8A C4A C4 117.2(3) . . ?
C6 C5 C4A 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C4A C5 H5 119.7 . . ?
C5 C6 C7 119.6(3) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 121.2(3) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C8A 120.5(3) . . ?
C7 C8 H8 119.8 . . ?
C8A C8 H8 119.8 . . ?
N1 C8A C4A 123.6(3) . . ?
N1 C8A C8 117.7(3) . . ?
C4A C8A C8 118.8(3) . . ?
C2 C21 H21A 109.5 . . ?
C2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O31 C31 C311 121.5(3) . . ?
O31 C31 C3 120.1(3) . . ?
C311 C31 C3 118.4(3) . . ?
C312 C311 C316 119.5(3) . . ?
C312 C311 C31 122.1(3) . . ?
C316 C311 C31 118.4(3) . . ?
C313 C312 C311 120.0(3) . . ?
C313 C312 H312 120.0 . . ?
C311 C312 H312 120.0 . . ?
C312 C313 C314 120.4(3) . . ?
C312 C313 H313 119.8 . . ?
C314 C313 H313 119.8 . . ?
C313 C314 C315 119.5(3) . . ?
C313 C314 H314 120.2 . . ?
C315 C314 H314 120.2 . . ?
C316 C315 C314 120.6(3) . . ?
C316 C315 H315 119.7 . . ?
C314 C315 H315 119.7 . . ?
C315 C316 C311 120.0(3) . . ?
C315 C316 H316 120.0 . . ?
C311 C316 H316 120.0 . . ?
C42 C41 C4 122.0(3) . . ?
C42 C41 H41 119.0 . . ?
C4 C41 H41 119.0 . . ?
C41 C42 C421 127.5(3) . . ?
C41 C42 H42 116.3 . . ?
C421 C42 H42 116.3 . . ?
C422 C421 C426 119.1(3) . . ?
C422 C421 C42 123.1(3) . . ?
C426 C421 C42 117.8(3) . . ?
C421 C422 C423 121.3(3) . . ?
C421 C422 H422 119.3 . . ?
C423 C422 H422 119.3 . . ?
C422 C423 C424 118.4(3) . . ?
C422 C423 C427 121.3(3) . . ?
C424 C423 C427 120.3(3) . . ?
C425 C424 C423 120.8(3) . . ?
C425 C424 H424 119.6 . . ?
C423 C424 H424 119.6 . . ?
C424 C425 C426 120.5(3) . . ?
C424 C425 H425 119.8 . . ?
C426 C425 H425 119.8 . . ?
C425 C426 C421 119.9(3) . . ?
C425 C426 H426 120.1 . . ?
C421 C426 H426 120.1 . . ?
C423 C427 H42A 109.5 . . ?
C423 C427 H42B 109.5 . . ?
H42A C427 H42B 109.5 . . ?
C423 C427 H42C 109.5 . . ?
H42A C427 H42C 109.5 . . ?
H42B C427 H42C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.316(4) . ?
N1 C8A 1.370(5) . ?
C2 C3 1.438(4) . ?
C2 C21 1.499(5) . ?
C3 C4 1.380(5) . ?
C3 C31 1.512(4) . ?
C4 C4A 1.434(4) . ?
C4 C41 1.478(4) . ?
C4A C5 1.414(5) . ?
C4A C8A 1.417(5) . ?
C5 C6 1.378(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.407(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.362(5) . ?
C7 H7 0.9500 . ?
C8 C8A 1.420(5) . ?
C8 H8 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C31 O31 1.216(4) . ?
C31 C311 1.489(5) . ?
C311 C312 1.393(5) . ?
C311 C316 1.398(4) . ?
C312 C313 1.383(5) . ?
C312 H312 0.9500 . ?
C313 C314 1.388(5) . ?
C313 H313 0.9500 . ?
C314 C315 1.389(5) . ?
C314 H314 0.9500 . ?
C315 C316 1.375(5) . ?
C315 H315 0.9500 . ?
C316 H316 0.9500 . ?
C41 C42 1.332(4) . ?
C41 H41 0.9500 . ?
C42 C421 1.475(4) . ?
C42 H42 0.9500 . ?
C421 C422 1.390(5) . ?
C421 C426 1.398(5) . ?
C422 C423 1.394(5) . ?
C422 H422 0.9500 . ?
C423 C424 1.394(5) . ?
C423 C427 1.504(5) . ?
C424 C425 1.381(5) . ?
C424 H424 0.9500 . ?
C425 C426 1.384(5) . ?
C425 H425 0.9500 . ?
C426 H426 0.9500 . ?
C427 H42A 0.9800 . ?
C427 H42B 0.9800 . ?
C427 H42C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C41 H41 O31 0.95 2.37 3.300(5) 167 8_556 no
C422 H422 O31 0.95 2.57 3.506(4) 169 8_556 no
C426 H426 Cg4 0.95 2.67 3.549(4) 155 6_755 no
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8A N1 C2 C3 -0.8(5) . . . . ?
C8A N1 C2 C21 178.0(3) . . . . ?
N1 C2 C3 C4 -0.8(5) . . . . ?
C21 C2 C3 C4 -179.6(3) . . . . ?
N1 C2 C3 C31 179.7(3) . . . . ?
C21 C2 C3 C31 0.9(5) . . . . ?
C2 C3 C4 C4A 3.0(5) . . . . ?
C31 C3 C4 C4A -177.5(3) . . . . ?
C2 C3 C4 C41 -173.7(3) . . . . ?
C31 C3 C4 C41 5.9(5) . . . . ?
C3 C4 C4A C5 177.6(3) . . . . ?
C41 C4 C4A C5 -5.7(5) . . . . ?
C3 C4 C4A C8A -3.5(5) . . . . ?
C41 C4 C4A C8A 173.2(3) . . . . ?
C8A C4A C5 C6 -0.2(5) . . . . ?
C4 C4A C5 C6 178.7(3) . . . . ?
C4A C5 C6 C7 -0.2(5) . . . . ?
C5 C6 C7 C8 0.4(6) . . . . ?
C6 C7 C8 C8A -0.2(5) . . . . ?
C2 N1 C8A C4A 0.2(5) . . . . ?
C2 N1 C8A C8 -179.2(3) . . . . ?
C5 C4A C8A N1 -179.0(3) . . . . ?
C4 C4A C8A N1 2.0(5) . . . . ?
C5 C4A C8A C8 0.3(5) . . . . ?
C4 C4A C8A C8 -178.6(3) . . . . ?
C7 C8 C8A N1 179.3(3) . . . . ?
C7 C8 C8A C4A -0.1(5) . . . . ?
C4 C3 C31 O31 -108.0(4) . . . . ?
C2 C3 C31 O31 71.5(4) . . . . ?
C4 C3 C31 C311 73.7(4) . . . . ?
C2 C3 C31 C311 -106.7(4) . . . . ?
O31 C31 C311 C312 -163.1(3) . . . . ?
C3 C31 C311 C312 15.1(5) . . . . ?
O31 C31 C311 C316 14.5(5) . . . . ?
C3 C31 C311 C316 -167.3(3) . . . . ?
C316 C311 C312 C313 -1.7(5) . . . . ?
C31 C311 C312 C313 175.9(3) . . . . ?
C311 C312 C313 C314 1.9(5) . . . . ?
C312 C313 C314 C315 -0.4(6) . . . . ?
C313 C314 C315 C316 -1.3(6) . . . . ?
C314 C315 C316 C311 1.6(6) . . . . ?
C312 C311 C316 C315 -0.1(5) . . . . ?
C31 C311 C316 C315 -177.7(3) . . . . ?
C3 C4 C41 C42 51.0(5) . . . . ?
C4A C4 C41 C42 -125.6(3) . . . . ?
C4 C41 C42 C421 177.7(3) . . . . ?
C41 C42 C421 C422 2.0(5) . . . . ?
C41 C42 C421 C426 -178.3(3) . . . . ?
C426 C421 C422 C423 -2.0(5) . . . . ?
C42 C421 C422 C423 177.7(3) . . . . ?
C421 C422 C423 C424 1.1(5) . . . . ?
C421 C422 C423 C427 -178.4(3) . . . . ?
C422 C423 C424 C425 0.5(5) . . . . ?
C427 C423 C424 C425 -179.9(3) . . . . ?
C423 C424 C425 C426 -1.3(5) . . . . ?
C424 C425 C426 C421 0.3(5) . . . . ?
C422 C421 C426 C425 1.3(5) . . . . ?
C42 C421 C426 C425 -178.5(3) . . . . ?
C42 C421 C426 C425 -178.5(3) . . . . ?
