#------------------------------------------------------------------------------
#$Date: 2019-11-23 21:33:32 +0200 (Sat, 23 Nov 2019) $
#$Revision: 235117 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/67/4036712.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_4036712
loop_
_publ_author_name
'Liu, Le'
'Zhang, Tonghuan'
'Yang, Yun-Fang'
'Zhang-Negrerie, Daisy'
'Zhang, Xinhao'
'Du, Yunfei'
'Wu, Yun-Dong'
'Zhao, Kang'
_publ_section_title
;
 Metal-Free Synthesis of 3-Arylquinolin-2-ones from Acrylic Amides via a
 Highly Regioselective 1,2-Aryl Migration: An Experimental and
 Computational Study.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4058
_journal_page_last               4065
_journal_paper_doi               10.1021/acs.joc.6b00345
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C22 H18 Cl N O'
_chemical_formula_weight         347.82
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.855(8)
_cell_length_b                   14.726(8)
_cell_length_c                   16.022(9)
_cell_measurement_reflns_used    9727
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      1.9
_cell_volume                     3505(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.22
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            34433
_diffrn_reflns_theta_full        27.84
_diffrn_reflns_theta_max         27.84
_diffrn_reflns_theta_min         2.33
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.9733
_exptl_absorpt_correction_T_min  0.9560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4156
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0611P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1126
_reflns_number_gt                3306
_reflns_number_total             4156
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00345_si_001.cif
_cod_data_source_block           m130224f1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4036712
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 1.05571(3) 0.77050(3) 0.18704(2) 0.03425(14) Uani 1 1 d .
O1 O 0.55947(6) 1.05245(7) 0.37901(7) 0.0302(3) Uani 1 1 d .
N1 N 0.65905(7) 1.10450(8) 0.47364(7) 0.0222(3) Uani 1 1 d .
C1 C 0.84904(9) 0.80062(10) 0.34315(9) 0.0239(3) Uani 1 1 d .
H1 H 0.8141 0.7631 0.3789 0.029 Uiso 1 1 calc R
C2 C 0.91682(10) 0.76210(10) 0.29551(9) 0.0258(3) Uani 1 1 d .
H2 H 0.9283 0.6987 0.2980 0.031 Uiso 1 1 calc R
C3 C 0.96733(9) 0.81770(10) 0.24421(9) 0.0250(3) Uani 1 1 d .
C4 C 0.95196(9) 0.91012(10) 0.23882(9) 0.0251(3) Uani 1 1 d .
H4 H 0.9875 0.9473 0.2033 0.030 Uiso 1 1 calc R
C5 C 0.88348(9) 0.94707(10) 0.28653(9) 0.0240(3) Uani 1 1 d .
H5 H 0.8719 1.0104 0.2831 0.029 Uiso 1 1 calc R
C6 C 0.83118(9) 0.89359(9) 0.33943(8) 0.0216(3) Uani 1 1 d .
C7 C 0.75986(9) 0.93515(10) 0.39231(9) 0.0211(3) Uani 1 1 d .
C8 C 0.75195(9) 0.90270(9) 0.47988(9) 0.0216(3) Uani 1 1 d .
C9 C 0.66836(10) 0.88717(10) 0.51642(10) 0.0268(3) Uani 1 1 d .
H9 H 0.6152 0.8959 0.4845 0.032 Uiso 1 1 calc R
C10 C 0.66161(11) 0.85901(11) 0.59890(10) 0.0325(4) Uani 1 1 d .
H10 H 0.6041 0.8489 0.6232 0.039 Uiso 1 1 calc R
C11 C 0.73882(11) 0.84574(10) 0.64556(10) 0.0326(4) Uani 1 1 d .
H11 H 0.7344 0.8260 0.7019 0.039 Uiso 1 1 calc R
C12 C 0.82271(11) 0.86114(10) 0.61032(10) 0.0305(4) Uani 1 1 d .
H12 H 0.8757 0.8528 0.6426 0.037 Uiso 1 1 calc R
C13 C 0.82906(10) 0.88872(10) 0.52798(9) 0.0254(3) Uani 1 1 d .
H13 H 0.8867 0.8983 0.5038 0.030 Uiso 1 1 calc R
C14 C 0.70832(9) 1.00149(9) 0.36126(9) 0.0234(3) Uani 1 1 d .
H14 H 0.7181 1.0170 0.3044 0.028 Uiso 1 1 calc R
C15 C 0.63744(9) 1.05370(9) 0.40569(9) 0.0229(3) Uani 1 1 d .
C16 C 0.58383(10) 1.14482(11) 0.51980(10) 0.0284(3) Uani 1 1 d .
H16A H 0.5439 1.1766 0.4808 0.043 Uiso 1 1 calc R
H16B H 0.6072 1.1880 0.5610 0.043 Uiso 1 1 calc R
H16C H 0.5502 1.0968 0.5484 0.043 Uiso 1 1 calc R
C17 C 0.74777(9) 1.11173(9) 0.50786(9) 0.0211(3) Uani 1 1 d .
C18 C 0.76100(10) 1.09711(10) 0.59279(9) 0.0257(3) Uani 1 1 d .
H18 H 0.7112 1.0837 0.6279 0.031 Uiso 1 1 calc R
C19 C 0.84665(10) 1.10222(10) 0.62578(10) 0.0287(3) Uani 1 1 d .
H19 H 0.8554 1.0934 0.6840 0.034 Uiso 1 1 calc R
C20 C 0.91966(10) 1.12002(10) 0.57522(9) 0.0284(3) Uani 1 1 d .
H20 H 0.9787 1.1213 0.5980 0.034 Uiso 1 1 calc R
C21 C 0.90623(10) 1.13611(10) 0.49085(10) 0.0267(3) Uani 1 1 d .
H21 H 0.9562 1.1491 0.4558 0.032 Uiso 1 1 calc R
C22 C 0.82045(10) 1.13335(9) 0.45755(9) 0.0236(3) Uani 1 1 d .
H22 H 0.8114 1.1463 0.4001 0.028 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C15 N1 C17 124.41(11)
C15 N1 C16 116.56(12)
C17 N1 C16 118.59(12)
C2 C1 C6 121.09(14)
C2 C1 H1 119.5
C6 C1 H1 119.5
C3 C2 C1 118.68(14)
C3 C2 H2 120.7
C1 C2 H2 120.7
C2 C3 C4 122.06(13)
C2 C3 Cl1 119.00(12)
C4 C3 Cl1 118.91(11)
C3 C4 C5 118.28(13)
C3 C4 H4 120.9
C5 C4 H4 120.9
C4 C5 C6 121.57(14)
C4 C5 H5 119.2
C6 C5 H5 119.2
C5 C6 C1 118.31(13)
C5 C6 C7 120.71(13)
C1 C6 C7 120.96(13)
C14 C7 C8 122.72(13)
C14 C7 C6 119.76(13)
C8 C7 C6 117.47(12)
C9 C8 C13 118.40(14)
C9 C8 C7 121.35(13)
C13 C8 C7 120.23(13)
C10 C9 C8 120.92(14)
C10 C9 H9 119.5
C8 C9 H9 119.5
C11 C10 C9 119.79(14)
C11 C10 H10 120.1
C9 C10 H10 120.1
C10 C11 C12 120.13(15)
C10 C11 H11 119.9
C12 C11 H11 119.9
C13 C12 C11 119.83(14)
C13 C12 H12 120.1
C11 C12 H12 120.1
C12 C13 C8 120.92(14)
C12 C13 H13 119.5
C8 C13 H13 119.5
C7 C14 C15 127.28(14)
C7 C14 H14 116.4
C15 C14 H14 116.4
O1 C15 N1 120.46(13)
O1 C15 C14 119.43(13)
N1 C15 C14 120.09(12)
N1 C16 H16A 109.5
N1 C16 H16B 109.5
H16A C16 H16B 109.5
N1 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C22 C17 C18 119.65(13)
C22 C17 N1 120.81(13)
C18 C17 N1 119.54(12)
C19 C18 C17 119.76(13)
C19 C18 H18 120.1
C17 C18 H18 120.1
C20 C19 C18 120.70(15)
C20 C19 H19 119.6
C18 C19 H19 119.6
C19 C20 C21 119.47(14)
C19 C20 H20 120.3
C21 C20 H20 120.3
C22 C21 C20 120.26(14)
C22 C21 H21 119.9
C20 C21 H21 119.9
C21 C22 C17 120.07(14)
C21 C22 H22 120.0
C17 C22 H22 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C3 1.7451(16)
O1 C15 1.2349(17)
N1 C15 1.3594(18)
N1 C17 1.4314(18)
N1 C16 1.4655(18)
C1 C2 1.385(2)
C1 C6 1.396(2)
C1 H1 0.9500
C2 C3 1.382(2)
C2 H2 0.9500
C3 C4 1.383(2)
C4 C5 1.384(2)
C4 H4 0.9500
C5 C6 1.394(2)
C5 H5 0.9500
C6 C7 1.488(2)
C7 C14 1.337(2)
C7 C8 1.487(2)
C8 C9 1.392(2)
C8 C13 1.396(2)
C9 C10 1.389(2)
C9 H9 0.9500
C10 C11 1.383(2)
C10 H10 0.9500
C11 C12 1.387(2)
C11 H11 0.9500
C12 C13 1.384(2)
C12 H12 0.9500
C13 H13 0.9500
C14 C15 1.485(2)
C14 H14 0.9500
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
C17 C22 1.385(2)
C17 C18 1.392(2)
C18 C19 1.380(2)
C18 H18 0.9500
C19 C20 1.379(2)
C19 H19 0.9500
C20 C21 1.387(2)
C20 H20 0.9500
C21 C22 1.382(2)
C21 H21 0.9500
C22 H22 0.9500
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
C6 C1 C2 C3 0.4(2)
C1 C2 C3 C4 -0.3(2)
C1 C2 C3 Cl1 177.53(11)
C2 C3 C4 C5 -0.1(2)
Cl1 C3 C4 C5 -177.98(11)
C3 C4 C5 C6 0.5(2)
C4 C5 C6 C1 -0.4(2)
C4 C5 C6 C7 177.96(12)
C2 C1 C6 C5 -0.1(2)
C2 C1 C6 C7 -178.42(13)
C5 C6 C7 C14 39.8(2)
C1 C6 C7 C14 -141.91(14)
C5 C6 C7 C8 -137.68(14)
C1 C6 C7 C8 40.59(19)
C14 C7 C8 C9 44.1(2)
C6 C7 C8 C9 -138.45(14)
C14 C7 C8 C13 -134.65(15)
C6 C7 C8 C13 42.77(19)
C13 C8 C9 C10 0.4(2)
C7 C8 C9 C10 -178.39(13)
C8 C9 C10 C11 -0.3(2)
C9 C10 C11 C12 0.5(2)
C10 C11 C12 C13 -0.8(2)
C11 C12 C13 C8 1.0(2)
C9 C8 C13 C12 -0.8(2)
C7 C8 C13 C12 178.06(13)
C8 C7 C14 C15 0.6(2)
C6 C7 C14 C15 -176.77(13)
C17 N1 C15 O1 -178.56(13)
C16 N1 C15 O1 9.2(2)
C17 N1 C15 C14 -0.5(2)
C16 N1 C15 C14 -172.75(13)
C7 C14 C15 O1 -121.05(16)
C7 C14 C15 N1 60.9(2)
C15 N1 C17 C22 51.1(2)
C16 N1 C17 C22 -136.84(15)
C15 N1 C17 C18 -129.11(15)
C16 N1 C17 C18 42.96(19)
C22 C17 C18 C19 -1.5(2)
N1 C17 C18 C19 178.71(13)
C17 C18 C19 C20 -1.2(2)
C18 C19 C20 C21 2.3(2)
C19 C20 C21 C22 -0.7(2)
C20 C21 C22 C17 -2.0(2)
C18 C17 C22 C21 3.1(2)
N1 C17 C22 C21 -177.13(13)
