#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/70/7237093.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_7237093
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         'C19 H16 Br O3 P'
_chemical_formula_sum            'C19 H16 Br O3 P'
_chemical_formula_weight         403.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.472(9)
_cell_length_b                   17.116(13)
_cell_length_c                   18.240(14)
_cell_measurement_reflns_used    2625
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.004
_cell_measurement_theta_min      2.34
_cell_volume                     3582(5)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.1182
_diffrn_reflns_av_unetI/netI     0.0780
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23501
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.004
_diffrn_reflns_theta_max         25.004
_diffrn_reflns_theta_min         2.233
_exptl_absorpt_coefficient_mu    2.398
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'multi-scan '
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.850
_refine_diff_density_min         -0.807
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3164
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1216
_refine_ls_R_factor_gt           0.0705
_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)+(0.0947P)²+0.9558P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1681
_refine_ls_wR_factor_ref         0.1873
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1934
_reflns_number_total             3164
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8gc02918k2.cif
_cod_data_source_block           1_CCDC2
_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_database_code               7237093
_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Br1 Br 0.14024(8) 0.05112(5) 0.27135(4) 0.0773(4) Uani 1 1 d . .
C1 C 0.0850(5) 0.2565(4) 0.6328(3) 0.0603(17) Uani 1 1 d . .
H1B H 0.0732 0.2967 0.5993 0.072 Uiso 1 1 calc R U
C2 C 0.0031(6) 0.2407(5) 0.6856(4) 0.078(2) Uani 1 1 d . .
H2A H -0.0653 0.2698 0.6873 0.094 Uiso 1 1 calc R U
C3 C 0.0212(8) 0.1831(5) 0.7352(4) 0.086(2) Uani 1 1 d . .
H3A H -0.0344 0.1738 0.7713 0.103 Uiso 1 1 calc R U
C4 C 0.1195(8) 0.1386(5) 0.7333(4) 0.084(3) Uani 1 1 d . .
H4A H 0.1308 0.0991 0.7675 0.101 Uiso 1 1 calc R U
C5 C 0.2015(6) 0.1526(4) 0.6804(3) 0.0576(16) Uani 1 1 d . .
H5A H 0.2684 0.1221 0.6785 0.069 Uiso 1 1 calc R U
C6 C 0.1856(5) 0.2116(3) 0.6301(3) 0.0404(13) Uani 1 1 d . .
C7 C 0.3192(4) 0.3290(3) 0.5517(3) 0.0425(14) Uani 1 1 d . .
C8 C 0.3190(6) 0.3764(4) 0.6126(4) 0.0638(18) Uani 1 1 d . .
H8A H 0.3049 0.3556 0.6589 0.077 Uiso 1 1 calc R U
C9 C 0.3398(7) 0.4550(4) 0.6042(6) 0.088(3) Uani 1 1 d . .
H9A H 0.3388 0.4875 0.6450 0.106 Uiso 1 1 calc R U
C10 C 0.3618(6) 0.4859(5) 0.5366(7) 0.091(3) Uani 1 1 d . .
H10A H 0.3755 0.5392 0.5313 0.109 Uiso 1 1 calc R U
C11 C 0.3638(6) 0.4382(4) 0.4771(5) 0.082(3) Uani 1 1 d . .
H11A H 0.3798 0.4591 0.4311 0.099 Uiso 1 1 calc R U
C12 C 0.3423(5) 0.3593(4) 0.4839(4) 0.0573(17) Uani 1 1 d . .
H12A H 0.3434 0.3271 0.4429 0.069 Uiso 1 1 calc R U
C13 C 0.2592(4) 0.1837(3) 0.4793(3) 0.0361(12) Uani 1 1 d . .
C14 C 0.3236(5) 0.1212(3) 0.4525(3) 0.0433(14) Uani 1 1 d . .
H14A H 0.3893 0.1051 0.4783 0.052 Uiso 1 1 calc R U
C15 C 0.2941(5) 0.0825(3) 0.3900(3) 0.0461(14) Uani 1 1 d . .
C16 C 0.1929(6) 0.1065(3) 0.3531(3) 0.0469(15) Uani 1 1 d . .
C17 C 0.1303(5) 0.1696(3) 0.3768(3) 0.0497(15) Uani 1 1 d . .
H17A H 0.0659 0.1863 0.3500 0.060 Uiso 1 1 calc R U
C18 C 0.1614(5) 0.2088(3) 0.4398(3) 0.0400(13) Uani 1 1 d . .
C19 C 0.4455(7) -0.0096(4) 0.4017(4) 0.093(3) Uani 1 1 d . .
H19A H 0.4794 -0.0529 0.3758 0.140 Uiso 1 1 calc R U
H19B H 0.5032 0.0303 0.4085 0.140 Uiso 1 1 calc R U
H19C H 0.4178 -0.0270 0.4486 0.140 Uiso 1 1 calc R U
O1 O 0.4096(3) 0.18821(19) 0.59201(18) 0.0389(9) Uani 1 1 d . .
O2 O 0.1040(3) 0.2716(2) 0.4660(2) 0.0543(11) Uani 1 1 d . .
H2B H 0.0484 0.2815 0.4393 0.081 Uiso 1 1 calc R U
O3 O 0.3517(4) 0.0207(3) 0.3608(2) 0.0729(14) Uani 1 1 d . .
P1 P 0.30020(12) 0.22613(8) 0.56447(7) 0.0355(4) 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'
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
C2 C1 C6 119.0(6)
C3 C2 C1 120.5(7)
C2 C3 C4 121.1(7)
C3 C4 C5 119.3(7)
C4 C5 C6 120.5(7)
C5 C6 C1 119.5(5)
C5 C6 P1 116.7(4)
C1 C6 P1 123.8(4)
C12 C7 C8 120.5(6)
C12 C7 P1 121.0(5)
C8 C7 P1 118.3(5)
C9 C8 C7 119.1(8)
C10 C9 C8 120.8(8)
C11 C10 C9 119.5(7)
C10 C11 C12 120.9(8)
C7 C12 C11 119.2(7)
C14 C13 C18 118.8(5)
C14 C13 P1 118.7(4)
C18 C13 P1 122.4(4)
C15 C14 C13 122.4(5)
O3 C15 C14 126.0(5)
O3 C15 C16 116.2(5)
C14 C15 C16 117.8(5)
C17 C16 C15 120.9(5)
C17 C16 Br1 118.9(5)
C15 C16 Br1 120.2(4)
C16 C17 C18 120.8(5)
O2 C18 C17 123.8(5)
O2 C18 C13 117.0(5)
C17 C18 C13 119.2(5)
C15 O3 C19 116.8(5)
O1 P1 C13 109.7(2)
O1 P1 C7 111.6(2)
C13 P1 C7 108.7(3)
O1 P1 C6 109.3(2)
C13 P1 C6 109.4(2)
C7 P1 C6 108.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C16 1.867(5)
C1 C2 1.372(9)
C1 C6 1.387(8)
C2 C3 1.355(10)
C3 C4 1.361(11)
C4 C5 1.368(9)
C5 C6 1.376(8)
C6 P1 1.795(5)
C7 C12 1.366(8)
C7 C8 1.376(8)
C7 P1 1.790(6)
C8 C9 1.374(9)
C9 C10 1.366(13)
C10 C11 1.358(13)
C11 C12 1.379(9)
C13 C14 1.389(7)
C13 C18 1.401(7)
C13 P1 1.779(5)
C14 C15 1.361(8)
C15 O3 1.357(7)
C15 C16 1.403(8)
C16 C17 1.368(8)
C17 C18 1.377(8)
C18 O2 1.349(6)
C19 O3 1.409(8)
O1 P1 1.499(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339922
