#------------------------------------------------------------------------------
#$Date: 2020-08-14 07:43:26 +0300 (Fri, 14 Aug 2020) $
#$Revision: 255313 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/22/2022226.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_2022226
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_coeditor_code           SK3755
_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_iupac          'C20 H16 Br N O'
_chemical_formula_moiety         'C20 H16 Br N O'
_chemical_formula_sum            'C20 H16 Br N O'
_chemical_formula_weight         366.24
_chemical_name_common
;
(E)-3-Acetyl-4-(4-bromostyryl)-2-methylquinoline
;
_chemical_name_systematic
;
(E)-3-Acetyl-4-[2-(4-bromophenyl)ethenyl]-2-methylquinoline
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 95.0050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0849(3)
_cell_length_b                   6.6692(2)
_cell_length_c                   31.1063(10)
_cell_measurement_reflns_used    3839
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.526
_cell_measurement_theta_min      2.529
_cell_volume                     1670.85(10)
_computing_cell_refinement
;
SAINT (Bruker, 2017)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2017)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_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  0.0335
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            38342
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_min         2.529
_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    2.464
_exptl_absorpt_correction_T_max  0.906
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.764
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3839
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0294P)²+1.5332P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0734
_reflns_number_gt                3434
_reflns_number_total             3839
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sk3755sup1.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2022226
_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   0.679
_shelx_estimated_absorpt_t_max   0.908
_shelxl_version_number           2.014
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.22878(18) 0.4980(2) 0.46764(5) 0.0216(3) Uani d 1 . .
C C2 0.3566(2) 0.4009(2) 0.45402(5) 0.0214(3) Uani d 1 . .
C C3 0.4453(2) 0.4719(2) 0.41918(5) 0.0198(3) Uani d 1 . .
C C4 0.3970(2) 0.6464(2) 0.39805(5) 0.0198(3) Uani d 1 . .
C C4A 0.2553(2) 0.7499(2) 0.41163(5) 0.0211(3) Uani d 1 . .
C C5 0.1897(2) 0.9251(3) 0.39104(6) 0.0314(4) Uani d 1 . .
H H5 0.2403 0.9788 0.3671 0.038 Uiso calc 1 . .
C C6 0.0535(3) 1.0184(3) 0.40534(7) 0.0358(5) Uani d 1 . .
H H6 0.0093 1.1347 0.3909 0.043 Uiso calc 1 . .
C C7 -0.0209(2) 0.9429(3) 0.44112(6) 0.0302(4) Uani d 1 . .
H H7 -0.1138 1.0101 0.4511 0.036 Uiso calc 1 . .
C C8 0.0395(2) 0.7731(3) 0.46174(6) 0.0249(3) Uani d 1 . .
H H8 -0.0110 0.7237 0.4861 0.030 Uiso calc 1 . .
C C8A 0.1770(2) 0.6713(2) 0.44684(5) 0.0203(3) Uani d 1 . .
C C21 0.4107(2) 0.2140(3) 0.47846(6) 0.0290(4) Uani d 1 . .
H H21A 0.3457 0.1989 0.5034 0.043 Uiso calc 1 . .
H H21B 0.5288 0.2242 0.4884 0.043 Uiso calc 1 . .
H H21C 0.3927 0.0972 0.4595 0.043 Uiso calc 1 . .
C C31 0.5978(2) 0.3597(3) 0.40803(6) 0.0248(3) Uani d 1 . .
O O31 0.58723(19) 0.1923(2) 0.39267(5) 0.0402(3) Uani d 1 . .
C C32 0.7612(2) 0.4597(3) 0.41940(7) 0.0315(4) Uani d 1 . .
H H32A 0.7915 0.4466 0.4505 0.047 Uiso calc 1 . .
H H32B 0.7527 0.6021 0.4117 0.047 Uiso calc 1 . .
H H32C 0.8465 0.3961 0.4035 0.047 Uiso calc 1 . .
C C41 0.4876(2) 0.7319(3) 0.36336(5) 0.0221(3) Uani d 1 . .
H H41 0.5115 0.8713 0.3646 0.026 Uiso calc 1 . .
C C42 0.5388(2) 0.6286(3) 0.33029(5) 0.0218(3) Uani d 1 . .
H H42 0.5101 0.4906 0.3282 0.026 Uiso calc 1 . .
C C421 0.63654(19) 0.7121(3) 0.29676(5) 0.0223(3) Uani d 1 . .
C C422 0.7176(2) 0.8969(3) 0.30115(6) 0.0263(4) Uani d 1 . .
H H422 0.7123 0.9718 0.3270 0.032 Uiso calc 1 . .
C C423 0.8056(2) 0.9731(3) 0.26847(6) 0.0298(4) Uani d 1 . .
H H423 0.8603 1.0989 0.2717 0.036 Uiso calc 1 . .
C C424 0.8123(2) 0.8621(3) 0.23090(6) 0.0303(4) Uani d 1 . .
Br Br42 0.93043(2) 0.96822(4) 0.18577(2) 0.04244(9) Uani d 1 . .
C C425 0.7361(2) 0.6784(4) 0.22581(6) 0.0368(5) Uani d 1 . .
H H425 0.7429 0.6037 0.2000 0.044 Uiso calc 1 . .
C C426 0.6488(2) 0.6033(3) 0.25888(6) 0.0304(4) Uani d 1 . .
H H426 0.5967 0.4758 0.2556 0.037 Uiso calc 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'
Br Br -0.2901 2.4595 '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
C2 N1 C8A . . 118.51(14) ?
N1 C2 C3 . . 122.57(15) ?
N1 C2 C21 . . 116.44(15) ?
C3 C2 C21 . . 120.94(15) ?
C4 C3 C2 . . 120.10(15) ?
C4 C3 C31 . . 120.88(15) ?
C2 C3 C31 . . 118.92(14) ?
C3 C4 C4A . . 117.88(15) ?
C3 C4 C41 . . 122.63(14) ?
C4A C4 C41 . . 119.47(14) ?
C8A C4A C5 . . 118.84(15) ?
C8A C4A C4 . . 118.27(15) ?
C5 C4A C4 . . 122.89(15) ?
C6 C5 C4A . . 120.53(17) ?
C6 C5 H5 . . 119.7 ?
C4A C5 H5 . . 119.7 ?
C5 C6 C7 . . 120.41(17) ?
C5 C6 H6 . . 119.8 ?
C7 C6 H6 . . 119.8 ?
C8 C7 C6 . . 120.49(16) ?
C8 C7 H7 . . 119.8 ?
C6 C7 H7 . . 119.8 ?
C7 C8 C8A . . 120.09(16) ?
C7 C8 H8 . . 120.0 ?
C8A C8 H8 . . 120.0 ?
N1 C8A C4A . . 122.63(15) ?
N1 C8A C8 . . 117.77(15) ?
C4A C8A C8 . . 119.59(15) ?
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 C32 . . 122.29(16) ?
O31 C31 C3 . . 121.02(17) ?
C32 C31 C3 . . 116.59(15) ?
C31 C32 H32A . . 109.5 ?
C31 C32 H32B . . 109.5 ?
H32A C32 H32B . . 109.5 ?
C31 C32 H32C . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
C42 C41 C4 . . 125.02(16) ?
C42 C41 H41 . . 117.5 ?
C4 C41 H41 . . 117.5 ?
C41 C42 C421 . . 124.98(16) ?
C41 C42 H42 . . 117.5 ?
C421 C42 H42 . . 117.5 ?
C426 C421 C422 . . 118.32(16) ?
C426 C421 C42 . . 118.94(16) ?
C422 C421 C42 . . 122.74(15) ?
C423 C422 C421 . . 121.18(17) ?
C423 C422 H422 . . 119.4 ?
C421 C422 H422 . . 119.4 ?
C422 C423 C424 . . 118.80(18) ?
C422 C423 H423 . . 120.6 ?
C424 C423 H423 . . 120.6 ?
C425 C424 C423 . . 121.48(17) ?
C425 C424 Br42 . . 119.71(14) ?
C423 C424 Br42 . . 118.81(15) ?
C424 C425 C426 . . 119.16(17) ?
C424 C425 H425 . . 120.4 ?
C426 C425 H425 . . 120.4 ?
C425 C426 C421 . . 121.04(18) ?
C425 C426 H426 . . 119.5 ?
C421 C426 H426 . . 119.5 ?
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
N1 C2 . 1.321(2) ?
N1 C8A . 1.372(2) ?
C2 C3 . 1.431(2) ?
C2 C21 . 1.505(2) ?
C3 C4 . 1.377(2) ?
C3 C31 . 1.509(2) ?
C4 C4A . 1.432(2) ?
C4 C41 . 1.471(2) ?
C4A C8A . 1.413(2) ?
C4A C5 . 1.413(2) ?
C5 C6 . 1.372(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.404(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.371(3) ?
C7 H7 . 0.9500 ?
C8 C8A . 1.415(2) ?
C8 H8 . 0.9500 ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
C31 O31 . 1.214(2) ?
C31 C32 . 1.495(3) ?
C32 H32A . 0.9800 ?
C32 H32B . 0.9800 ?
C32 H32C . 0.9800 ?
C41 C42 . 1.334(2) ?
C41 H41 . 0.9500 ?
C42 C421 . 1.472(2) ?
C42 H42 . 0.9500 ?
C421 C426 . 1.395(2) ?
C421 C422 . 1.397(3) ?
C422 C423 . 1.387(3) ?
C422 H422 . 0.9500 ?
C423 C424 . 1.388(3) ?
C423 H423 . 0.9500 ?
C424 C425 . 1.375(3) ?
C424 Br42 . 1.9018(17) ?
C425 C426 . 1.390(3) ?
C425 H425 . 0.9500 ?
C426 H426 . 0.9500 ?
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
_geom_hbond_publ_flag
C41 H41 O31 1_565 0.95 2.37 3.283(2) 161 no
C426 H426 Cg3 2_645 0.95 2.91 3.7071(19) 142 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8A N1 C2 C3 . . . . 1.5(2) ?
C8A N1 C2 C21 . . . . 178.81(15) ?
N1 C2 C3 C4 . . . . -0.9(3) ?
C21 C2 C3 C4 . . . . -178.04(16) ?
N1 C2 C3 C31 . . . . 175.33(15) ?
C21 C2 C3 C31 . . . . -1.8(2) ?
C2 C3 C4 C4A . . . . -1.1(2) ?
C31 C3 C4 C4A . . . . -177.20(15) ?
C2 C3 C4 C41 . . . . 177.13(15) ?
C31 C3 C4 C41 . . . . 1.0(2) ?
C3 C4 C4A C8A . . . . 2.2(2) ?
C41 C4 C4A C8A . . . . -176.01(15) ?
C3 C4 C4A C5 . . . . -176.96(17) ?
C41 C4 C4A C5 . . . . 4.8(3) ?
C8A C4A C5 C6 . . . . 0.7(3) ?
C4 C4A C5 C6 . . . . 179.93(19) ?
C4A C5 C6 C7 . . . . 1.1(3) ?
C5 C6 C7 C8 . . . . -1.2(3) ?
C6 C7 C8 C8A . . . . -0.5(3) ?
C2 N1 C8A C4A . . . . -0.2(2) ?
C2 N1 C8A C8 . . . . 179.77(15) ?
C5 C4A C8A N1 . . . . 177.56(16) ?
C4 C4A C8A N1 . . . . -1.7(2) ?
C5 C4A C8A C8 . . . . -2.4(2) ?
C4 C4A C8A C8 . . . . 178.33(15) ?
C7 C8 C8A N1 . . . . -177.65(16) ?
C7 C8 C8A C4A . . . . 2.3(3) ?
C4 C3 C31 O31 . . . . -115.6(2) ?
C2 C3 C31 O31 . . . . 68.2(2) ?
C4 C3 C31 C32 . . . . 68.1(2) ?
C2 C3 C31 C32 . . . . -108.09(18) ?
C3 C4 C41 C42 . . . . 46.8(3) ?
C4A C4 C41 C42 . . . . -135.02(18) ?
C4 C41 C42 C421 . . . . -176.86(15) ?
C41 C42 C421 C426 . . . . -165.04(17) ?
C41 C42 C421 C422 . . . . 14.8(3) ?
C426 C421 C422 C423 . . . . 1.2(3) ?
C42 C421 C422 C423 . . . . -178.57(16) ?
C421 C422 C423 C424 . . . . 0.0(3) ?
C422 C423 C424 C425 . . . . -1.0(3) ?
C422 C423 C424 Br42 . . . . 179.13(14) ?
C423 C424 C425 C426 . . . . 0.7(3) ?
Br42 C424 C425 C426 . . . . -179.40(15) ?
C424 C425 C426 C421 . . . . 0.6(3) ?
C422 C421 C426 C425 . . . . -1.5(3) ?
C42 C421 C426 C425 . . . . 178.30(17) ?

_cod_database_fobs_code 2022226
