#------------------------------------------------------------------------------
#$Date: 2020-04-04 02:29:42 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250020 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/81/4038180.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_4038180
loop_
_publ_author_name
'Chao, Tung'
'Su, Zhe-Hong'
'Yen, Ko-Wang'
'Wu, Ming-Jung'
'Chu, Jean-Ho'
_publ_section_title
;
 Synthesis of Dibenzosuberones Bearing an Isoxazole Group via
 Palladium-Catalyzed Intramolecular C-H/C-Br Bond Cross-Coupling of
 Ortho-Aroylated 3,5-Diarylisoxazoles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00346
_journal_year                    2020
_chemical_formula_moiety         'C22 H14 Br N O2'
_chemical_formula_sum            'C22 H14 Br N O2'
_chemical_formula_weight         404.25
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 105.042(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1968(8)
_cell_length_b                   13.1506(9)
_cell_length_c                   13.4564(11)
_cell_measurement_reflns_used    3197
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.20
_cell_measurement_theta_min      2.58
_cell_volume                     1742.6(2)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX2'
_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  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11609
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    2.375
_exptl_absorpt_correction_T_max  0.9540
_exptl_absorpt_correction_T_min  0.5772
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0671P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1101
_reflns_number_gt                2114
_reflns_number_total             3090
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00346_si_002.cif
_cod_data_source_block           ch19204
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038180
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5089(3) 0.67982(19) 0.7030(2) 0.0341(7) Uani 1 1 d . . .
C2 C 0.4230(3) 0.6037(2) 0.6615(2) 0.0332(7) Uani 1 1 d . . .
C3 C 0.4362(3) 0.49632(19) 0.6370(2) 0.0327(7) Uani 1 1 d . . .
C4 C 0.5538(3) 0.4588(2) 0.6160(3) 0.0411(8) Uani 1 1 d . . .
H4 H 0.6283 0.5014 0.6220 0.049 Uiso 1 1 calc R . .
C5 C 0.5609(4) 0.3591(2) 0.5863(3) 0.0487(9) Uani 1 1 d . . .
H5 H 0.6398 0.3346 0.5723 0.058 Uiso 1 1 calc R . .
C6 C 0.4507(4) 0.2956(2) 0.5774(3) 0.0531(10) Uani 1 1 d . . .
H6 H 0.4547 0.2288 0.5558 0.064 Uiso 1 1 calc R . .
C7 C 0.3356(4) 0.3305(2) 0.6002(3) 0.0564(11) Uani 1 1 d . . .
H7 H 0.2625 0.2868 0.5957 0.068 Uiso 1 1 calc R . .
C8 C 0.3271(3) 0.4303(2) 0.6298(3) 0.0418(8) Uani 1 1 d . . .
H8 H 0.2484 0.4535 0.6450 0.050 Uiso 1 1 calc R . .
C9 C 0.4263(3) 0.76598(19) 0.7041(2) 0.0361(8) Uani 1 1 d . . .
C10 C 0.4672(3) 0.8685(2) 0.7480(3) 0.0348(8) Uani 1 1 d . . .
C11 C 0.5386(3) 0.8746(2) 0.8498(3) 0.0443(9) Uani 1 1 d . . .
H11 H 0.5630 0.8152 0.8875 0.053 Uiso 1 1 calc R . .
C12 C 0.5747(3) 0.9677(2) 0.8970(3) 0.0485(9) Uani 1 1 d . . .
H12 H 0.6246 0.9707 0.9655 0.058 Uiso 1 1 calc R . .
C13 C 0.5363(4) 1.0558(2) 0.8421(3) 0.0482(9) Uani 1 1 d . . .
H13 H 0.5593 1.1186 0.8736 0.058 Uiso 1 1 calc R . .
C14 C 0.4639(3) 1.0510(2) 0.7407(3) 0.0430(9) Uani 1 1 d . . .
H14 H 0.4368 1.1111 0.7048 0.052 Uiso 1 1 calc R . .
C15 C 0.4302(3) 0.95825(19) 0.6906(3) 0.0355(8) Uani 1 1 d . . .
C16 C 0.3678(3) 0.9571(2) 0.5773(3) 0.0393(8) Uani 1 1 d . . .
C17 C 0.2546(3) 1.02909(18) 0.5334(3) 0.0347(8) Uani 1 1 d . . .
C18 C 0.1644(3) 1.0595(2) 0.5889(3) 0.0399(8) Uani 1 1 d . . .
H18 H 0.1787 1.0393 0.6571 0.048 Uiso 1 1 calc R . .
C19 C 0.0537(3) 1.1195(2) 0.5441(3) 0.0471(9) Uani 1 1 d . . .
H19 H -0.0076 1.1377 0.5815 0.056 Uiso 1 1 calc R . .
C20 C 0.0342(4) 1.1520(2) 0.4449(3) 0.0509(10) Uani 1 1 d . . .
H20 H -0.0403 1.1927 0.4150 0.061 Uiso 1 1 calc R . .
C21 C 0.1242(4) 1.1249(3) 0.3891(3) 0.0538(10) Uani 1 1 d . . .
H21 H 0.1116 1.1484 0.3220 0.065 Uiso 1 1 calc R . .
C22 C 0.2337(4) 1.0627(2) 0.4325(3) 0.0474(9) Uani 1 1 d . . .
H22 H 0.2933 1.0433 0.3941 0.057 Uiso 1 1 calc R . .
N1 N 0.2984(3) 0.74492(17) 0.6650(2) 0.0489(8) Uani 1 1 d . . .
O1 O 0.2947(2) 0.64130(14) 0.63663(18) 0.0444(6) Uani 1 1 d . . .
O2 O 0.4110(3) 0.89998(17) 0.52236(19) 0.0600(7) Uani 1 1 d . . .
Br1 Br 0.69601(3) 0.67443(3) 0.75383(4) 0.0668(2) Uani 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9 105.9(3) . . ?
C2 C1 Br1 128.2(2) . . ?
C9 C1 Br1 125.8(2) . . ?
C1 C2 O1 108.2(2) . . ?
C1 C2 C3 136.0(3) . . ?
O1 C2 C3 115.8(2) . . ?
C4 C3 C8 118.6(3) . . ?
C4 C3 C2 121.5(3) . . ?
C8 C3 C2 119.8(3) . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.9(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 120.3(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.4(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C3 120.2(3) . . ?
C7 C8 H8 119.9 . . ?
C3 C8 H8 119.9 . . ?
N1 C9 C1 111.2(2) . . ?
N1 C9 C10 120.1(3) . . ?
C1 C9 C10 128.6(3) . . ?
C11 C10 C15 119.6(3) . . ?
C11 C10 C9 118.0(3) . . ?
C15 C10 C9 122.4(3) . . ?
C10 C11 C12 121.2(3) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 121.5(3) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C10 118.2(3) . . ?
C14 C15 C16 119.3(3) . . ?
C10 C15 C16 122.3(2) . . ?
O2 C16 C17 121.2(3) . . ?
O2 C16 C15 120.2(3) . . ?
C17 C16 C15 118.6(3) . . ?
C18 C17 C22 118.7(3) . . ?
C18 C17 C16 121.6(3) . . ?
C22 C17 C16 119.7(3) . . ?
C19 C18 C17 120.8(3) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C18 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.2(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C22 120.1(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 120.1(3) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?
C9 N1 O1 105.5(2) . . ?
C2 O1 N1 109.2(2) . . ?
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
C1 C2 1.352(4) . ?
C1 C9 1.414(4) . ?
C1 Br1 1.854(3) . ?
C2 O1 1.356(3) . ?
C2 C3 1.465(4) . ?
C3 C4 1.392(4) . ?
C3 C8 1.395(4) . ?
C4 C5 1.378(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.368(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 N1 1.303(4) . ?
C9 C10 1.487(4) . ?
C10 C11 1.377(4) . ?
C10 C15 1.407(4) . ?
C11 C12 1.384(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.393(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.493(5) . ?
C16 O2 1.214(4) . ?
C16 C17 1.491(4) . ?
C17 C18 1.385(4) . ?
C17 C22 1.391(4) . ?
C18 C19 1.380(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.367(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.376(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(5) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
N1 O1 1.413(3) . ?
