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#$Date: 2019-11-11 20:00:32 +0200 (Mon, 11 Nov 2019) $
#$Revision: 227186 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/57/4035738.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_4035738
loop_
_publ_author_name
'Mamedov, Vakhid A.'
'Mamedova, Vera L.'
'Kadyrova, Saniya F.'
'Galimullina, Venera R.'
'Khikmatova, Gul'naz Z.'
'Korshin, Dmitry E.'
'Gubaidullin, Aidar T.'
'Krivolapov, Dmitry B.'
'Rizvanov, Il'dar Kh'
'Bazanova, Olga B.'
'Sinyashin, Oleg G.'
'Latypov, Shamil K.'
_publ_section_title
;
 Synthesis of 3-Hydroxy-4-arylquinolin-2-ones Including Viridicatol via a
 Darzens Condensation/Friedel-Crafts Alkylation Strategy.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13132
_journal_page_last               13145
_journal_paper_doi               10.1021/acs.joc.8b01871
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C16 H13 Br Cl N O2'
_chemical_formula_sum            'C16 H13 Br Cl N O2'
_chemical_formula_weight         366.63
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.045(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7083(11)
_cell_length_b                   12.3985(9)
_cell_length_c                   9.9543(9)
_cell_measurement_reflns_used    2010
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.48
_cell_measurement_theta_min      2.79
_cell_volume                     1625.9(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1073
_diffrn_reflns_av_unetI/netI     0.1827
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20243
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.764
_diffrn_reflns_theta_min         3.093
_exptl_absorpt_coefficient_mu    2.695
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.4824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 G.M. Sheldrick (1998a). SADABS v.2.01, Bruker.
 Siemens Area Detector Absorption Correction Program.
 Bruker AXS. Madison. Wisconsin. USA
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.824
_exptl_crystal_size_mid          0.723
_exptl_crystal_size_min          0.194
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.888
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         6348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.888
_refine_ls_R_factor_all          0.2673
_refine_ls_R_factor_gt           0.0573
_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)+(0.0734P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1860
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1743
_reflns_number_total             6348
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b01871_si_008.cif
_cod_data_source_block           vakh_viri8
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035738
_shelx_shelxl_version_number     2014/7
_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   0.215
_shelx_estimated_absorpt_t_max   0.623
_exptl_absorpt_special_details
;
 Additional spherical absorption correction applied with mu*r =  0.2000
 Lambda/2 correction factor = 0.0015
;
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_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
Br1 Br 0.50736(4) 0.86058(5) 1.21320(7) 0.0960(3) Uani 1 1 d . .
Cl1 Cl 0.23086(9) 0.37871(8) 1.05373(11) 0.0681(3) Uani 1 1 d . .
N1 N 0.0667(2) 0.3654(2) 0.6793(3) 0.0466(8) Uani 1 1 d . .
C5 C 0.2624(3) 0.5965(3) 1.0535(3) 0.0400(8) Uani 1 1 d . .
O2 O -0.0054(2) 0.4012(2) 0.8530(3) 0.0583(7) Uani 1 1 d . .
C2 C 0.0601(3) 0.4180(3) 0.7929(4) 0.0400(8) Uani 1 1 d . .
C12 C 0.1448(3) 0.3878(3) 0.6126(4) 0.0493(10) Uani 1 1 d . .
O3 O 0.13767(19) 0.5873(2) 0.7756(3) 0.0487(6) Uani 1 1 d . .
C4 C 0.1818(3) 0.5127(3) 1.0060(4) 0.0427(9) Uani 1 1 d . .
C17 C 0.2451(3) 0.3741(3) 0.6814(5) 0.0583(11) Uani 1 1 d . .
H17 H 0.2647 0.3485 0.7728 0.070 Uiso 1 1 calc R U
C7 C 0.3160(3) 0.7609(3) 1.1760(5) 0.0665(12) Uani 1 1 d . .
H7 H 0.3030 0.8185 1.2284 0.080 Uiso 1 1 calc R U
C10 C 0.3534(3) 0.5915(3) 1.0227(4) 0.0587(11) Uani 1 1 d . .
H10 H 0.3669 0.5337 0.9710 0.070 Uiso 1 1 calc R U
C6 C 0.2440(3) 0.6822(3) 1.1306(4) 0.0527(10) Uani 1 1 d . .
H6 H 0.1824 0.6868 1.1523 0.063 Uiso 1 1 calc R U
C11 C -0.0112(4) 0.2846(4) 0.6170(6) 0.0893(16) Uani 1 1 d . .
H111 H 0.0032 0.2534 0.5364 0.134 Uiso 1 1 calc R U
H113 H -0.0111 0.2291 0.6843 0.134 Uiso 1 1 calc R U
H112 H -0.0767 0.3186 0.5898 0.134 Uiso 1 1 calc R U
C8 C 0.4059(3) 0.7548(3) 1.1445(4) 0.0559(10) Uani 1 1 d . .
C9 C 0.4254(3) 0.6705(4) 1.0668(5) 0.0646(12) Uani 1 1 d . .
H9 H 0.4867 0.6668 1.0442 0.078 Uiso 1 1 calc R U
C16 C 0.3170(4) 0.3991(4) 0.6116(6) 0.0821(15) Uani 1 1 d . .
H16 H 0.3856 0.3901 0.6568 0.098 Uiso 1 1 calc R U
C15 C 0.2888(6) 0.4358(5) 0.4804(8) 0.113(2) Uani 1 1 d . .
H15 H 0.3380 0.4555 0.4368 0.136 Uiso 1 1 calc R U
C13 C 0.1169(4) 0.4205(4) 0.4753(5) 0.0811(15) Uani 1 1 d . .
H13 H 0.0485 0.4260 0.4271 0.097 Uiso 1 1 calc R U
C14 C 0.1885(5) 0.4448(5) 0.4097(6) 0.113(2) Uani 1 1 d . .
H14 H 0.1694 0.4674 0.3170 0.136 Uiso 1 1 calc R U
C3 C 0.1323(2) 0.5123(3) 0.8479(4) 0.0364(8) Uani 1 1 d . .
H4 H 0.122(3) 0.525(3) 1.042(4) 0.053(10) Uiso 1 1 d . .
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'
Cl Cl 0.1484 0.1585 '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
C2 N1 C12 122.3(3)
C2 N1 C11 118.7(3)
C12 N1 C11 119.0(3)
C10 C5 C6 118.7(3)
C10 C5 C4 122.6(3)
C6 C5 C4 118.7(3)
O2 C2 N1 124.2(3)
O2 C2 C3 116.3(3)
N1 C2 C3 119.3(3)
C17 C12 C13 120.0(4)
C17 C12 N1 121.3(4)
C13 C12 N1 118.7(4)
C5 C4 C3 113.9(3)
C5 C4 Cl1 111.5(2)
C3 C4 Cl1 107.1(2)
C5 C4 H4 113.1(19)
C3 C4 H4 101(2)
Cl1 C4 H4 109(2)
C12 C17 C16 118.5(4)
C12 C17 H17 120.8
C16 C17 H17 120.8
C8 C7 C6 120.1(4)
C8 C7 H7 120.0
C6 C7 H7 120.0
C5 C10 C9 121.1(4)
C5 C10 H10 119.5
C9 C10 H10 119.5
C7 C6 C5 120.5(3)
C7 C6 H6 119.8
C5 C6 H6 119.8
N1 C11 H111 109.5
N1 C11 H113 109.5
H111 C11 H113 109.5
N1 C11 H112 109.5
H111 C11 H112 109.5
H113 C11 H112 109.5
C7 C8 C9 120.3(4)
C7 C8 Br1 120.1(3)
C9 C8 Br1 119.5(3)
C8 C9 C10 119.3(4)
C8 C9 H9 120.3
C10 C9 H9 120.3
C15 C16 C17 120.8(5)
C15 C16 H16 119.6
C17 C16 H16 119.6
C16 C15 C14 120.7(5)
C16 C15 H15 119.7
C14 C15 H15 119.7
C14 C13 C12 120.4(5)
C14 C13 H13 119.8
C12 C13 H13 119.8
C13 C14 C15 119.6(5)
C13 C14 H14 120.2
C15 C14 H14 120.2
O3 C3 C4 122.3(3)
O3 C3 C2 121.4(3)
C4 C3 C2 115.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C8 1.897(4)
Cl1 C4 1.805(4)
N1 C2 1.330(4)
N1 C12 1.434(5)
N1 C11 1.471(5)
C5 C10 1.365(5)
C5 C6 1.375(5)
C5 C4 1.495(5)
O2 C2 1.226(4)
C2 C3 1.532(5)
C12 C17 1.366(6)
C12 C13 1.375(6)
O3 C3 1.191(4)
C4 C3 1.532(5)
C4 H4 0.99(4)
C17 C16 1.389(7)
C17 H17 0.9300
C7 C8 1.355(5)
C7 C6 1.372(5)
C7 H7 0.9300
C10 C9 1.374(6)
C10 H10 0.9300
C6 H6 0.9300
C11 H111 0.9600
C11 H113 0.9600
C11 H112 0.9600
C8 C9 1.370(6)
C9 H9 0.9300
C16 C15 1.336(8)
C16 H16 0.9300
C15 C14 1.365(8)
C15 H15 0.9300
C13 C14 1.354(7)
C13 H13 0.9300
C14 H14 0.9300
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
C12 N1 C2 O2 -179.9(3)
C11 N1 C2 O2 2.7(6)
C12 N1 C2 C3 5.3(5)
C11 N1 C2 C3 -172.2(4)
C2 N1 C12 C17 61.4(5)
C11 N1 C12 C17 -121.2(4)
C2 N1 C12 C13 -120.7(4)
C11 N1 C12 C13 56.8(5)
C10 C5 C4 C3 -68.9(5)
C6 C5 C4 C3 110.8(4)
C10 C5 C4 Cl1 52.5(4)
C6 C5 C4 Cl1 -127.8(3)
C13 C12 C17 C16 3.2(6)
N1 C12 C17 C16 -178.9(4)
C6 C5 C10 C9 -0.4(6)
C4 C5 C10 C9 179.3(4)
C8 C7 C6 C5 0.2(7)
C10 C5 C6 C7 -0.2(6)
C4 C5 C6 C7 -179.9(4)
C6 C7 C8 C9 0.3(7)
C6 C7 C8 Br1 -177.6(3)
C7 C8 C9 C10 -0.8(7)
Br1 C8 C9 C10 177.1(3)
C5 C10 C9 C8 0.9(7)
C12 C17 C16 C15 0.1(7)
C17 C16 C15 C14 -3.1(10)
C17 C12 C13 C14 -3.5(7)
N1 C12 C13 C14 178.5(5)
C12 C13 C14 C15 0.5(9)
C16 C15 C14 C13 2.9(11)
C5 C4 C3 O3 -18.5(5)
Cl1 C4 C3 O3 -142.4(3)
C5 C4 C3 C2 171.9(3)
Cl1 C4 C3 C2 48.1(3)
O2 C2 C3 O3 -119.2(4)
N1 C2 C3 O3 56.1(5)
O2 C2 C3 C4 50.5(4)
N1 C2 C3 C4 -134.3(3)
