#------------------------------------------------------------------------------
#$Date: 2020-07-04 04:55:26 +0300 (Sat, 04 Jul 2020) $
#$Revision: 253737 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/85/4038500.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_4038500
loop_
_publ_author_name
'Tong, Zhou'
'Tang, Zhi'
'Au, Chak-Tong'
'Qiu, Renhua'
_publ_section_title
;
 Nickel-Catalyzed Decarbonyloxidation of 3-Aryl
 Benzofuran-2(3H)-ones to 2-Hydroxybenzophenones.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8533
_journal_page_last               8543
_journal_paper_doi               10.1021/acs.joc.0c00858
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C13 H9 Cl O2'
_chemical_formula_sum            'C13 H9 Cl O2'
_chemical_formula_weight         232.65
_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     dual
_audit_creation_date             2018-05-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.921(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3318(8)
_cell_length_b                   5.8627(3)
_cell_length_c                   11.9302(7)
_cell_measurement_reflns_used    2193
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.0890
_cell_measurement_theta_min      3.4440
_cell_volume                     1036.20(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -35.00  51.00   1.00    1.20    --  -11.59  37.00 120.00   86
  2  ω     -9.00  23.00   1.00    1.20    --  -11.59 -99.00-150.00   32
  3  ω     -1.00  72.00   1.00    1.20    --   11.74  37.00-120.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0061230000
_diffrn_orient_matrix_UB_12      -0.1192966000
_diffrn_orient_matrix_UB_13      -0.0083318000
_diffrn_orient_matrix_UB_21      -0.0473601000
_diffrn_orient_matrix_UB_22      0.0161595000
_diffrn_orient_matrix_UB_23      -0.0188384000
_diffrn_orient_matrix_UB_31      0.0032093000
_diffrn_orient_matrix_UB_32      0.0119333000
_diffrn_orient_matrix_UB_33      -0.0579964000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4160
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.750
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1814
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0343
_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)+(0.0393P)²+0.2233P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0871
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1575
_reflns_number_total             1814
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00858_si_002.cif
_cod_data_source_block           exp_1468
_cod_depositor_comments          'Adding full bibliography for 4038500.cif.'
_cod_original_cell_volume        1036.19(10)
_cod_database_code               4038500
_shelx_shelxl_version_number     2018/3
_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.
;
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C2(H2), C3(H3), C13(H13), C10(H10), C11(H11), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_date_sample_data_collection 2018-05-16
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.502
_oxdiff_exptl_absorpt_empirical_full_min 0.705
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.92391(3) 0.22080(8) 0.50383(4) 0.02436(17) Uani 1 1 d . . . . .
O1 O 0.79061(9) 1.0181(2) 0.70494(10) 0.0226(3) Uani 1 1 d . . . . .
H1 H 0.757451 1.096081 0.654484 0.034 Uiso 1 1 calc GR . . . .
O2 O 0.69575(8) 1.1169(2) 0.49978(10) 0.0225(3) Uani 1 1 d . . . . .
C6 C 0.81467(11) 0.5859(3) 0.49206(14) 0.0166(4) Uani 1 1 d . . . . .
H6 H 0.794030 0.551263 0.413602 0.020 Uiso 1 1 calc R . . . .
C5 C 0.78041(11) 0.7763(3) 0.53740(14) 0.0155(4) Uani 1 1 d . . . . .
C8 C 0.66383(11) 0.8587(3) 0.34407(14) 0.0162(4) Uani 1 1 d . . . . .
C4 C 0.81526(12) 0.8286(3) 0.65644(15) 0.0175(4) Uani 1 1 d . . . . .
C7 C 0.71319(11) 0.9288(3) 0.46416(15) 0.0173(4) Uani 1 1 d . . . . .
C9 C 0.62083(11) 0.6488(3) 0.32143(15) 0.0176(4) Uani 1 1 d . . . . .
H9 H 0.626482 0.541878 0.380467 0.021 Uiso 1 1 calc R . . . .
C2 C 0.90871(12) 0.4944(3) 0.68160(15) 0.0210(4) Uani 1 1 d . . . . .
H2 H 0.950064 0.397289 0.729412 0.025 Uiso 1 1 calc R . . . .
C1 C 0.87861(12) 0.4501(3) 0.56305(15) 0.0189(4) Uani 1 1 d . . . . .
C3 C 0.87677(12) 0.6827(3) 0.72734(15) 0.0210(4) Uani 1 1 d . . . . .
H3 H 0.896584 0.712467 0.806412 0.025 Uiso 1 1 calc R . . . .
C13 C 0.65621(11) 1.0170(3) 0.25475(14) 0.0184(4) Uani 1 1 d . . . . .
H13 H 0.683963 1.158700 0.270123 0.022 Uiso 1 1 calc R . . . .
C10 C 0.56928(11) 0.5993(3) 0.21000(15) 0.0191(4) Uani 1 1 d . . . . .
H10 H 0.538803 0.460987 0.194831 0.023 Uiso 1 1 calc R . . . .
C11 C 0.56343(12) 0.7566(3) 0.12162(15) 0.0213(5) Uani 1 1 d . . . . .
H11 H 0.529561 0.722752 0.046923 0.026 Uiso 1 1 calc R . . . .
C12 C 0.60768(12) 0.9636(3) 0.14394(15) 0.0207(4) Uani 1 1 d . . . . .
H12 H 0.604635 1.066952 0.083932 0.025 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'
Cl Cl 0.1484 0.1585 '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
C1 C6 C5 120.21(16) . . ?
C6 C5 C4 118.55(16) . . ?
C6 C5 C7 122.04(15) . . ?
C4 C5 C7 119.33(17) . . ?
C9 C8 C7 121.84(16) . . ?
C9 C8 C13 119.89(17) . . ?
C13 C8 C7 118.12(17) . . ?
O1 C4 C5 122.20(16) . . ?
O1 C4 C3 117.84(15) . . ?
C3 C4 C5 119.96(17) . . ?
O2 C7 C5 121.27(16) . . ?
O2 C7 C8 118.28(16) . . ?
C5 C7 C8 120.44(17) . . ?
C8 C9 C10 119.67(17) . . ?
C3 C2 C1 119.51(17) . . ?
C6 C1 Cl1 119.51(14) . . ?
C6 C1 C2 121.02(17) . . ?
C2 C1 Cl1 119.46(14) . . ?
C2 C3 C4 120.54(16) . . ?
C12 C13 C8 120.06(18) . . ?
C11 C10 C9 119.84(18) . . ?
C12 C11 C10 120.34(17) . . ?
C13 C12 C11 120.14(17) . . ?
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
Cl1 C1 1.7441(19) . ?
O1 C4 1.350(2) . ?
O2 C7 1.236(2) . ?
C6 C5 1.400(3) . ?
C6 C1 1.373(3) . ?
C5 C4 1.416(2) . ?
C5 C7 1.470(3) . ?
C8 C7 1.495(2) . ?
C8 C9 1.390(3) . ?
C8 C13 1.395(2) . ?
C4 C3 1.388(3) . ?
C9 C10 1.391(2) . ?
C2 C1 1.394(2) . ?
C2 C3 1.377(3) . ?
C13 C12 1.376(2) . ?
C10 C11 1.386(3) . ?
C11 C12 1.382(3) . ?
