#------------------------------------------------------------------------------
#$Date: 2020-04-04 02:29:21 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250019 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/81/4038179.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_4038179
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         'C23 H15 N O3'
_chemical_formula_sum            'C23 H15 N O3'
_chemical_formula_weight         353.36
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                112.013(3)
_cell_angle_beta                 90.901(3)
_cell_angle_gamma                96.228(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9312(5)
_cell_length_b                   9.4412(5)
_cell_length_c                   10.9587(6)
_cell_measurement_reflns_used    3956
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.15
_cell_measurement_theta_min      2.44
_cell_volume                     850.04(8)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2005)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6761
_diffrn_reflns_theta_full        25.27
_diffrn_reflns_theta_max         25.27
_diffrn_reflns_theta_min         2.96
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9854
_exptl_absorpt_correction_T_min  0.9350
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.74
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0782P)²+0.1318P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1259
_reflns_number_gt                2621
_reflns_number_total             3077
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00346_si_006.cif
_cod_data_source_block           ch19997
_cod_original_cell_volume        850.03(8)
_cod_database_code               4038179
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.48819(15) 0.70245(16) 0.46548(14) 0.0424(3) Uani 1 1 d . . .
C2 C 0.36918(15) 0.79808(16) 0.52345(14) 0.0413(3) Uani 1 1 d . . .
C3 C 0.40656(17) 0.95044(17) 0.61081(14) 0.0449(4) Uani 1 1 d . . .
H3 H 0.5073 0.9925 0.6291 0.054 Uiso 1 1 calc R . .
C4 C 0.29584(18) 1.03878(17) 0.66991(15) 0.0494(4) Uani 1 1 d . . .
H4 H 0.3219 1.1410 0.7258 0.059 Uiso 1 1 calc R . .
C5 C 0.14529(17) 0.97627(17) 0.64666(15) 0.0471(4) Uani 1 1 d . . .
C6 C -0.10958(19) 1.0089(2) 0.7040(2) 0.0703(5) Uani 1 1 d . . .
H6A H -0.1672 1.0871 0.7576 0.105 Uiso 1 1 calc R . .
H6B H -0.1190 0.9242 0.7328 0.105 Uiso 1 1 calc R . .
H6C H -0.1467 0.9736 0.6136 0.105 Uiso 1 1 calc R . .
C7 C 0.10604(17) 0.82566(18) 0.55961(16) 0.0503(4) Uani 1 1 d . . .
H7 H 0.0052 0.7838 0.5420 0.060 Uiso 1 1 calc R . .
C8 C 0.21801(16) 0.73817(17) 0.49912(15) 0.0475(4) Uani 1 1 d . . .
H8 H 0.1914 0.6370 0.4409 0.057 Uiso 1 1 calc R . .
C9 C 0.50720(15) 0.58640(15) 0.34861(14) 0.0398(3) Uani 1 1 d . . .
C10 C 0.41179(15) 0.52294(16) 0.22466(14) 0.0400(3) Uani 1 1 d . . .
C11 C 0.32568(17) 0.61738(18) 0.18841(16) 0.0500(4) Uani 1 1 d . . .
H11 H 0.3286 0.7204 0.2434 0.060 Uiso 1 1 calc R . .
C12 C 0.2362(2) 0.5606(2) 0.07238(17) 0.0592(4) Uani 1 1 d . . .
H12 H 0.1807 0.6257 0.0496 0.071 Uiso 1 1 calc R . .
C13 C 0.2288(2) 0.4075(2) -0.00997(17) 0.0602(4) Uani 1 1 d . . .
H13 H 0.1683 0.3692 -0.0880 0.072 Uiso 1 1 calc R . .
C14 C 0.31159(18) 0.31293(18) 0.02456(15) 0.0518(4) Uani 1 1 d . . .
H14 H 0.3055 0.2095 -0.0302 0.062 Uiso 1 1 calc R . .
C15 C 0.40479(15) 0.36840(16) 0.13995(14) 0.0417(3) Uani 1 1 d . . .
C16 C 0.49492(17) 0.25304(16) 0.16108(14) 0.0440(4) Uani 1 1 d . . .
C17 C 0.66225(16) 0.29031(16) 0.18489(14) 0.0430(3) Uani 1 1 d . . .
C18 C 0.74866(19) 0.17815(17) 0.10802(16) 0.0531(4) Uani 1 1 d . . .
H18 H 0.7007 0.0844 0.0490 0.064 Uiso 1 1 calc R . .
C19 C 0.90329(19) 0.2046(2) 0.11861(18) 0.0596(5) Uani 1 1 d . . .
H19 H 0.9592 0.1296 0.0656 0.071 Uiso 1 1 calc R . .
C20 C 0.97631(18) 0.3417(2) 0.20734(19) 0.0603(5) Uani 1 1 d . . .
H20 H 1.0812 0.3589 0.2149 0.072 Uiso 1 1 calc R . .
C21 C 0.89347(17) 0.45278(19) 0.28449(17) 0.0544(4) Uani 1 1 d . . .
H21 H 0.9432 0.5452 0.3441 0.065 Uiso 1 1 calc R . .
C22 C 0.73621(16) 0.42950(16) 0.27518(15) 0.0432(3) Uani 1 1 d . . .
C23 C 0.65323(15) 0.54688(16) 0.36709(14) 0.0431(3) Uani 1 1 d . . .
N1 N 0.71748(13) 0.63189(15) 0.48396(14) 0.0541(4) Uani 1 1 d . . .
O1 O 0.61276(11) 0.73150(12) 0.54749(10) 0.0527(3) Uani 1 1 d . . .
O2 O 0.04489(13) 1.07097(13) 0.71591(13) 0.0663(4) Uani 1 1 d . . .
O3 O 0.43487(13) 0.12390(12) 0.14133(12) 0.0593(3) 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'
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
O1 C1 C9 109.39(12) . . ?
O1 C1 C2 113.95(12) . . ?
C9 C1 C2 136.64(13) . . ?
C8 C2 C3 118.35(13) . . ?
C8 C2 C1 121.29(12) . . ?
C3 C2 C1 120.26(12) . . ?
C4 C3 C2 120.61(13) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.36(13) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
O2 C5 C7 124.45(14) . . ?
O2 C5 C4 115.74(13) . . ?
C7 C5 C4 119.80(14) . . ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C5 119.46(14) . . ?
C8 C7 H7 120.3 . . ?
C5 C7 H7 120.3 . . ?
C7 C8 C2 121.39(13) . . ?
C7 C8 H8 119.3 . . ?
C2 C8 H8 119.3 . . ?
C1 C9 C23 103.74(13) . . ?
C1 C9 C10 130.31(13) . . ?
C23 C9 C10 125.68(12) . . ?
C11 C10 C15 118.04(14) . . ?
C11 C10 C9 120.23(13) . . ?
C15 C10 C9 121.72(13) . . ?
C12 C11 C10 121.20(15) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C11 120.36(15) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 119.23(16) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 121.39(15) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C10 119.75(14) . . ?
C14 C15 C16 115.34(13) . . ?
C10 C15 C16 124.89(13) . . ?
O3 C16 C17 120.22(14) . . ?
O3 C16 C15 119.90(13) . . ?
C17 C16 C15 119.14(12) . . ?
C18 C17 C22 118.87(14) . . ?
C18 C17 C16 116.58(13) . . ?
C22 C17 C16 124.52(13) . . ?
C19 C18 C17 120.84(15) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 120.36(15) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C21 C20 C19 119.68(15) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 121.21(15) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C21 C22 C17 119.04(14) . . ?
C21 C22 C23 118.99(13) . . ?
C17 C22 C23 121.82(13) . . ?
N1 C23 C9 112.23(13) . . ?
N1 C23 C22 118.55(13) . . ?
C9 C23 C22 129.21(13) . . ?
C23 N1 O1 105.28(11) . . ?
C1 O1 N1 109.36(11) . . ?
C5 O2 C6 118.11(13) . . ?
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 O1 1.3558(17) . ?
C1 C9 1.366(2) . ?
C1 C2 1.4655(19) . ?
C2 C8 1.3871(19) . ?
C2 C3 1.3967(19) . ?
C3 C4 1.374(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(2) . ?
C4 H4 0.9300 . ?
C5 O2 1.3660(18) . ?
C5 C7 1.385(2) . ?
C6 O2 1.423(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.382(2) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C23 1.4266(19) . ?
C9 C10 1.474(2) . ?
C10 C11 1.396(2) . ?
C10 C15 1.399(2) . ?
C11 C12 1.381(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.394(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.504(2) . ?
C16 O3 1.2156(17) . ?
C16 C17 1.493(2) . ?
C17 C18 1.398(2) . ?
C17 C22 1.400(2) . ?
C18 C19 1.372(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.373(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.394(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.4686(19) . ?
C23 N1 1.3115(19) . ?
N1 O1 1.4016(16) . ?
