#------------------------------------------------------------------------------
#$Date: 2022-09-20 11:32:02 +0300 (Tue, 20 Sep 2022) $
#$Revision: 277994 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/56/1555698.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_1555698
loop_
_publ_author_name
'Xiang, Jia-Chen'
'Cheng, Yan'
'Wang, Miao'
'Wu, Yan-Dong'
'Wu, An-Xin'
_publ_section_title
;
 Direct Construction of 4-Hydroxybenzils via Para-Selective C-C Bond
 Coupling of Phenols and Aryl Methyl Ketones.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4360
_journal_page_last               4363
_journal_paper_doi               10.1021/acs.orglett.6b02118
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C15 H12 O3'
_chemical_formula_weight         240.24
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 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                 100.249(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.771(5)
_cell_length_b                   8.568(3)
_cell_length_c                   20.892(8)
_cell_measurement_reflns_used    1932
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.81
_cell_volume                     2425.7(15)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6799
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.98
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9819
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.807
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2347
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0618
_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)+(0.0890P)²+4.4576P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1716
_refine_ls_wR_factor_ref         0.1859
_reflns_number_gt                1759
_reflns_number_total             2347
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b02118_si_002.cif
_cod_data_source_block           mo_150416b_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' 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 

2022-09-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C30 H24 O6'
_cod_original_formula_weight         480.49
_cod_original_formula_units_Z            4
_cod_original_cell_volume        2425.7(16)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1555698
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C1 C 0.4016(2) 0.4694(3) 0.58925(13) 0.0237(6) Uani 1 1 d .
C2 C 0.3697(2) 0.4003(3) 0.52814(13) 0.0247(6) Uani 1 1 d .
H2 H 0.3049 0.4212 0.5054 0.030 Uiso 1 1 calc R
C3 C 0.4300(2) 0.3031(3) 0.50041(13) 0.0243(6) Uani 1 1 d .
C4 C 0.5263(2) 0.2757(3) 0.53434(13) 0.0239(6) Uani 1 1 d .
C5 C 0.5594(2) 0.3436(3) 0.59487(13) 0.0251(6) Uani 1 1 d .
H5 H 0.6247 0.3243 0.6171 0.030 Uiso 1 1 calc R
C6 C 0.4975(2) 0.4390(3) 0.62257(13) 0.0248(6) Uani 1 1 d .
H6 H 0.5197 0.4839 0.6642 0.030 Uiso 1 1 calc R
C7 C 0.3945(2) 0.2225(3) 0.43430(13) 0.0277(6) Uani 1 1 d .
H7A H 0.3282 0.2598 0.4157 0.042 Uiso 1 1 calc R
H7B H 0.3929 0.1093 0.4406 0.042 Uiso 1 1 calc R
H7C H 0.4400 0.2473 0.4046 0.042 Uiso 1 1 calc R
C8 C 0.3357(2) 0.5754(3) 0.61611(14) 0.0269(6) Uani 1 1 d .
C9 C 0.3643(2) 0.6382(3) 0.68530(14) 0.0271(6) Uani 1 1 d .
C10 C 0.3639(2) 0.8092(3) 0.69546(14) 0.0268(6) Uani 1 1 d .
C11 C 0.3649(2) 0.9130(3) 0.64414(14) 0.0295(7) Uani 1 1 d .
H11 H 0.3634 0.8745 0.6013 0.035 Uiso 1 1 calc R
C12 C 0.3681(2) 1.0724(3) 0.65564(16) 0.0366(7) Uani 1 1 d .
H12 H 0.3695 1.1432 0.6208 0.044 Uiso 1 1 calc R
C13 C 0.3694(3) 1.1283(4) 0.71801(17) 0.0413(8) Uani 1 1 d .
H13 H 0.3712 1.2376 0.7259 0.050 Uiso 1 1 calc R
C14 C 0.3681(3) 1.0252(4) 0.76891(17) 0.0403(8) Uani 1 1 d .
H14 H 0.3687 1.0639 0.8116 0.048 Uiso 1 1 calc R
C15 C 0.3661(2) 0.8666(4) 0.75779(15) 0.0331(7) Uani 1 1 d .
H15 H 0.3662 0.7962 0.7930 0.040 Uiso 1 1 calc R
O1 O 0.58426(15) 0.1824(2) 0.50555(10) 0.0305(5) Uani 1 1 d D
H1 H 0.6395(13) 0.174(4) 0.5282(15) 0.046 Uiso 1 1 d D
O2 O 0.25348(15) 0.6127(2) 0.58706(10) 0.0361(6) Uani 1 1 d .
O3 O 0.37839(16) 0.5436(2) 0.72966(10) 0.0368(6) 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'
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
C6 C1 C2 119.1(2)
C6 C1 C8 121.2(2)
C2 C1 C8 119.7(2)
C3 C2 C1 121.6(2)
C3 C2 H2 119.2
C1 C2 H2 119.2
C2 C3 C4 118.3(2)
C2 C3 C7 121.9(2)
C4 C3 C7 119.7(2)
O1 C4 C5 122.0(2)
O1 C4 C3 117.1(2)
C5 C4 C3 121.0(3)
C6 C5 C4 120.1(3)
C6 C5 H5 120.0
C4 C5 H5 120.0
C5 C6 C1 119.9(3)
C5 C6 H6 120.0
C1 C6 H6 120.0
C3 C7 H7A 109.5
C3 C7 H7B 109.5
H7A C7 H7B 109.5
C3 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
O2 C8 C1 123.5(3)
O2 C8 C9 115.9(3)
C1 C8 C9 120.5(2)
O3 C9 C10 123.5(3)
O3 C9 C8 117.7(3)
C10 C9 C8 118.5(2)
C15 C10 C11 119.6(3)
C15 C10 C9 119.0(3)
C11 C10 C9 121.3(3)
C12 C11 C10 120.0(3)
C12 C11 H11 120.0
C10 C11 H11 120.0
C13 C12 C11 119.9(3)
C13 C12 H12 120.1
C11 C12 H12 120.1
C14 C13 C12 120.1(3)
C14 C13 H13 119.9
C12 C13 H13 119.9
C15 C14 C13 120.1(3)
C15 C14 H14 119.9
C13 C14 H14 119.9
C14 C15 C10 120.3(3)
C14 C15 H15 119.9
C10 C15 H15 119.9
C4 O1 H1 111(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.404(4)
C1 C2 1.405(4)
C1 C8 1.464(4)
C2 C3 1.375(4)
C2 H2 0.9500
C3 C4 1.407(4)
C3 C7 1.544(4)
C4 O1 1.345(3)
C4 C5 1.393(4)
C5 C6 1.380(4)
C5 H5 0.9500
C6 H6 0.9500
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 O2 1.228(3)
C8 C9 1.527(4)
C9 O3 1.220(3)
C9 C10 1.481(4)
C10 C15 1.387(4)
C10 C11 1.395(4)
C11 C12 1.386(4)
C11 H11 0.9500
C12 C13 1.385(5)
C12 H12 0.9500
C13 C14 1.385(5)
C13 H13 0.9500
C14 C15 1.378(5)
C14 H14 0.9500
C15 H15 0.9500
O1 H1 0.824(10)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.824(10) 1.889(14) 2.697(3) 167(4) 3_545
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 0.3(4)
C8 C1 C2 C3 178.4(2)
C1 C2 C3 C4 -1.0(4)
C1 C2 C3 C7 178.0(2)
C2 C3 C4 O1 -178.8(2)
C7 C3 C4 O1 2.1(4)
C2 C3 C4 C5 0.7(4)
C7 C3 C4 C5 -178.3(2)
O1 C4 C5 C6 179.8(2)
C3 C4 C5 C6 0.3(4)
C4 C5 C6 C1 -1.0(4)
C2 C1 C6 C5 0.7(4)
C8 C1 C6 C5 -177.3(3)
C6 C1 C8 O2 175.5(3)
C2 C1 C8 O2 -2.5(4)
C6 C1 C8 C9 -8.5(4)
C2 C1 C8 C9 173.5(2)
O2 C8 C9 O3 116.4(3)
C1 C8 C9 O3 -59.9(4)
O2 C8 C9 C10 -57.7(4)
C1 C8 C9 C10 126.0(3)
O3 C9 C10 C15 -9.1(4)
C8 C9 C10 C15 164.6(3)
O3 C9 C10 C11 168.5(3)
C8 C9 C10 C11 -17.8(4)
C15 C10 C11 C12 0.0(4)
C9 C10 C11 C12 -177.6(3)
C10 C11 C12 C13 -0.6(5)
C11 C12 C13 C14 0.4(5)
C12 C13 C14 C15 0.3(5)
C13 C14 C15 C10 -0.9(5)
C11 C10 C15 C14 0.8(5)
C9 C10 C15 C14 178.4(3)
