#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/70/7237094.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_7237094
loop_
_publ_author_name
'Shen, Ruwei'
'Zhang, Ming'
'Xiao, Jing'
'Dong, Chao'
'Han, Li-Biao'
_publ_section_title
;
 Ph3P-mediated highly selective C(α)--P coupling of quinone monoacetals
 with R2P(O)H: convenient and practical synthesis of ortho-phosphinyl
 phenols
;
_journal_issue                   22
_journal_name_full               'Green Chemistry'
_journal_page_first              5111
_journal_paper_doi               10.1039/C8GC02918K
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C20 H19 O3 P'
_chemical_formula_sum            'C20 H19 O3 P'
_chemical_formula_weight         338.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-04-28 deposited with the CCDC.
2018-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.109(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.086(10)
_cell_length_b                   11.245(6)
_cell_length_c                   17.491(10)
_cell_measurement_reflns_used    2625
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.004
_cell_measurement_theta_min      2.14
_cell_volume                     3522(3)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Apex2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12250
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.004
_diffrn_reflns_theta_max         25.004
_diffrn_reflns_theta_min         2.139
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'multi-scan '
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0619P)²+0.5568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1287
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2121
_reflns_number_total             3108
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8gc02918k2.cif
_cod_data_source_block           1_CCDC3
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'multi-scan ' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/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      'C 2/c'
_cod_database_code               7237094
_shelx_shelxl_version_number     2014/7
_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.
;
_exptl_absorpt_special_details   '(SADABS; Sheldrick, 2003)'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.25152(16) 0.5937(2) 0.35863(15) 0.0554(7) Uani 1 1 d . .
H1A H 0.2949 0.6012 0.3360 0.066 Uiso 1 1 calc R U
C2 C 0.25305(19) 0.6183(3) 0.43695(16) 0.0668(9) Uani 1 1 d . .
H2A H 0.2975 0.6416 0.4666 0.080 Uiso 1 1 calc R U
C3 C 0.1897(2) 0.6081(3) 0.47012(17) 0.0734(9) Uani 1 1 d . .
H3A H 0.1910 0.6239 0.5225 0.088 Uiso 1 1 calc R U
C4 C 0.1242(2) 0.5748(3) 0.42680(17) 0.0779(10) Uani 1 1 d . .
H4A H 0.0808 0.5691 0.4495 0.093 Uiso 1 1 calc R U
C5 C 0.12221(17) 0.5495(3) 0.34949(16) 0.0644(8) Uani 1 1 d . .
H5A H 0.0775 0.5263 0.3205 0.077 Uiso 1 1 calc R U
C6 C 0.18586(15) 0.5584(2) 0.31453(13) 0.0435(6) Uani 1 1 d . .
C7 C 0.11846(13) 0.4143(2) 0.18619(14) 0.0431(6) Uani 1 1 d . .
C8 C 0.12168(16) 0.3085(2) 0.22761(18) 0.0629(8) Uani 1 1 d . .
H8A H 0.1547 0.3009 0.2732 0.075 Uiso 1 1 calc R U
C9 C 0.07594(18) 0.2147(3) 0.2012(2) 0.0775(10) Uani 1 1 d . .
H9A H 0.0787 0.1435 0.2285 0.093 Uiso 1 1 calc R U
C10 C 0.02612(18) 0.2266(3) 0.1345(2) 0.0771(10) Uani 1 1 d . .
H10A H -0.0047 0.1632 0.1167 0.093 Uiso 1 1 calc R U
C11 C 0.02177(18) 0.3303(3) 0.09439(19) 0.0750(9) Uani 1 1 d . .
H11A H -0.0122 0.3376 0.0495 0.090 Uiso 1 1 calc R U
C12 C 0.06732(15) 0.4251(3) 0.11975(15) 0.0566(7) Uani 1 1 d . .
H12A H 0.0636 0.4961 0.0922 0.068 Uiso 1 1 calc R U
C13 C 0.26997(13) 0.4988(2) 0.18784(13) 0.0394(6) Uani 1 1 d . .
C14 C 0.29434(14) 0.5561(2) 0.12470(13) 0.0429(6) Uani 1 1 d . .
H14A H 0.2666 0.6190 0.1010 0.051 Uiso 1 1 calc R U
C15 C 0.35858(14) 0.5210(2) 0.09732(14) 0.0447(6) Uani 1 1 d . .
C16 C 0.40188(14) 0.4287(2) 0.13239(15) 0.0476(6) Uani 1 1 d . .
C17 C 0.37899(14) 0.3738(2) 0.19618(14) 0.0478(7) Uani 1 1 d . .
H17A H 0.4082 0.3134 0.2210 0.057 Uiso 1 1 calc R U
C18 C 0.31370(14) 0.4067(2) 0.22392(13) 0.0426(6) Uani 1 1 d . .
C19 C 0.34353(18) 0.6671(3) -0.00408(17) 0.0732(9) Uani 1 1 d . .
H19A H 0.3676 0.6938 -0.0465 0.110 Uiso 1 1 calc R U
H19B H 0.2939 0.6406 -0.0231 0.110 Uiso 1 1 calc R U
H19C H 0.3411 0.7314 0.0316 0.110 Uiso 1 1 calc R U
C20 C 0.47168(17) 0.3871(3) 0.10161(18) 0.0712(9) Uani 1 1 d . .
H20A H 0.4793 0.4344 0.0577 0.107 Uiso 1 1 calc R U
H20B H 0.5140 0.3953 0.1411 0.107 Uiso 1 1 calc R U
H20C H 0.4661 0.3051 0.0865 0.107 Uiso 1 1 calc R U
O1 O 0.15028(9) 0.64735(14) 0.16846(9) 0.0465(4) Uani 1 1 d . .
O2 O 0.38498(10) 0.57150(18) 0.03415(10) 0.0596(5) Uani 1 1 d . .
O3 O 0.28992(10) 0.35240(15) 0.28583(9) 0.0547(5) Uani 1 1 d . .
H3B H 0.3123 0.2894 0.2947 0.082 Uiso 1 1 calc R U
P1 P 0.17996(4) 0.53838(6) 0.21210(3) 0.0403(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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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 120.2(3)
C3 C2 C1 120.1(3)
C2 C3 C4 120.2(3)
C3 C4 C5 120.1(3)
C4 C5 C6 120.8(3)
C1 C6 C5 118.6(2)
C1 C6 P1 121.3(2)
C5 C6 P1 119.8(2)
C12 C7 C8 119.1(2)
C12 C7 P1 117.3(2)
C8 C7 P1 123.6(2)
C9 C8 C7 120.1(3)
C10 C9 C8 120.0(3)
C11 C10 C9 120.3(3)
C10 C11 C12 120.6(3)
C11 C12 C7 119.9(3)
C18 C13 C14 118.4(2)
C18 C13 P1 123.42(18)
C14 C13 P1 117.92(19)
C15 C14 C13 121.1(2)
C14 C15 O2 124.2(2)
C14 C15 C16 120.8(2)
O2 C15 C16 115.0(2)
C17 C16 C15 118.2(2)
C17 C16 C20 120.4(2)
C15 C16 C20 121.3(2)
C18 C17 C16 121.8(2)
O3 C18 C17 122.5(2)
O3 C18 C13 117.9(2)
C17 C18 C13 119.6(2)
C15 O2 C19 117.8(2)
O1 P1 C6 111.83(11)
O1 P1 C13 110.67(11)
C6 P1 C13 109.82(11)
O1 P1 C7 109.90(11)
C6 P1 C7 107.21(12)
C13 P1 C7 107.25(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.380(4)
C1 C2 1.394(4)
C2 C3 1.360(4)
C3 C4 1.366(4)
C4 C5 1.377(4)
C5 C6 1.381(4)
C6 P1 1.794(3)
C7 C12 1.385(3)
C7 C8 1.390(4)
C7 P1 1.802(3)
C8 C9 1.379(4)
C9 C10 1.377(4)
C10 C11 1.358(4)
C11 C12 1.382(4)
C13 C18 1.399(3)
C13 C14 1.402(3)
C13 P1 1.795(3)
C14 C15 1.376(3)
C15 O2 1.386(3)
C15 C16 1.389(4)
C16 C17 1.389(3)
C16 C20 1.515(4)
C17 C18 1.388(3)
C18 O3 1.364(3)
C19 O2 1.422(3)
O1 P1 1.5023(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339923
