#------------------------------------------------------------------------------
#$Date: 2022-10-07 04:14:12 +0300 (Fri, 07 Oct 2022) $
#$Revision: 278465 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/17/7061759.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_7061759
loop_
_publ_author_name
'Wang, Jing'
'Li, Zenghui'
'You, Gaoqiang'
'Xu, Liang'
'Gao, Pin'
'Rao, Bin'
_publ_section_title
;
 Regioselective transformation of 3-phosphoryl benzyne intermediates to
 diverse phosphorus-substituted arenes
;
_journal_issue                   35
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              17049
_journal_page_last               17054
_journal_paper_doi               10.1039/D2NJ03638J
_journal_volume                  46
_journal_year                    2022
_chemical_formula_sum            'C22 H22 F3 O4 P S Si'
_chemical_formula_weight         498.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-03-02 deposited with the CCDC.	2022-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.9660(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4427(3)
_cell_length_b                   11.9566(2)
_cell_length_c                   17.3148(4)
_cell_measurement_reflns_used    9945
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.44
_cell_volume                     2421.14(9)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            47013
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.380
_diffrn_reflns_theta_min         2.114
_exptl_absorpt_coefficient_mu    0.298
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4954
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0412
_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)+(0.0594P)²+0.7517P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1169
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4026
_reflns_number_total             4954
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj03638j2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7061758--7061760.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7061759
_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.
;
_shelx_estimated_absorpt_t_min   0.974
_shelx_estimated_absorpt_t_max   0.979
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.16796(4) 0.64048(4) 0.72376(3) 0.04263(14) Uani 1 1 d . . . . .
S1 S 0.32585(5) 0.64551(5) 0.56974(3) 0.05441(16) Uani 1 1 d . . . . .
Si1 Si 0.63860(5) 0.62035(6) 0.73657(4) 0.05943(18) Uani 1 1 d . . . . .
O2 O 0.36472(10) 0.58849(10) 0.65638(7) 0.0443(3) Uani 1 1 d . . . . .
O1 O 0.15641(12) 0.53177(12) 0.68141(10) 0.0596(4) Uani 1 1 d . . . . .
F2 F 0.2214(3) 0.5410(3) 0.43406(12) 0.0805(7) Uani 0.807(6) 1 d . . P A 1
O4 O 0.24458(19) 0.73047(15) 0.56256(11) 0.0907(6) Uani 1 1 d . . . . .
C1 C 0.31479(14) 0.69278(14) 0.75990(11) 0.0412(4) Uani 1 1 d . . . . .
C2 C 0.39888(15) 0.65847(14) 0.72838(11) 0.0403(4) Uani 1 1 d . . . . .
C10 C 0.13026(15) 0.62911(15) 0.81569(12) 0.0450(4) Uani 1 1 d . . . . .
C16 C 0.07860(15) 0.74953(16) 0.66318(11) 0.0442(4) Uani 1 1 d . . . . .
C3 C 0.51444(16) 0.68131(17) 0.76381(12) 0.0485(4) Uani 1 1 d . . . . .
O3 O 0.41884(18) 0.6649(2) 0.54373(12) 0.1076(8) Uani 1 1 d . . . . .
C6 C 0.35051(17) 0.76247(17) 0.82819(13) 0.0542(5) Uani 1 1 d . . . . .
H6 H 0.2962 0.7886 0.8515 0.065 Uiso 1 1 calc R U . . .
C15 C 0.08851(17) 0.71767(18) 0.84892(13) 0.0531(5) Uani 1 1 d . . . . .
H15 H 0.0771 0.7886 0.8227 0.064 Uiso 1 1 calc R U . . .
C21 C 0.10689(18) 0.86248(17) 0.67051(13) 0.0540(5) Uani 1 1 d . . . . .
H21 H 0.1768 0.8864 0.7102 0.065 Uiso 1 1 calc R U . . .
C14 C 0.06353(19) 0.7029(2) 0.92001(14) 0.0607(5) Uani 1 1 d . . . . .
H14 H 0.0346 0.7637 0.9423 0.073 Uiso 1 1 calc R U . . .
C11 C 0.14411(19) 0.52608(19) 0.85474(15) 0.0621(6) Uani 1 1 d . . . . .
H11 H 0.1707 0.4641 0.8320 0.075 Uiso 1 1 calc R U . . .
C17 C -0.02526(18) 0.7173(2) 0.60626(14) 0.0643(6) Uani 1 1 d . . . . .
H17 H -0.0461 0.6405 0.6010 0.077 Uiso 1 1 calc R U . . .
C13 C 0.0801(2) 0.6013(2) 0.95867(15) 0.0666(6) Uani 1 1 d . . . . .
H13 H 0.0642 0.5922 1.0082 0.080 Uiso 1 1 calc R U . . .
F3 F 0.1426(3) 0.5214(3) 0.51829(15) 0.1274(16) Uani 0.807(6) 1 d . . P A 1
C4 C 0.54299(18) 0.7518(2) 0.83276(15) 0.0642(6) Uani 1 1 d . . . . .
H4 H 0.6210 0.7708 0.8597 0.077 Uiso 1 1 calc R U . . .
C19 C -0.0689(2) 0.9061(2) 0.56351(14) 0.0707(7) Uani 1 1 d . . . . .
H19 H -0.1191 0.9595 0.5288 0.085 Uiso 1 1 calc R U . . .
C20 C 0.0336(2) 0.9401(2) 0.62015(14) 0.0643(6) Uani 1 1 d . . . . .
H20 H 0.0539 1.0170 0.6246 0.077 Uiso 1 1 calc R U . . .
F1 F 0.2951(4) 0.43435(19) 0.53484(19) 0.158(3) Uani 0.807(6) 1 d . . P A 1
C5 C 0.46281(19) 0.7942(2) 0.86261(15) 0.0678(6) Uani 1 1 d . . . . .
H5 H 0.4849 0.8456 0.9071 0.081 Uiso 1 1 calc R U . . .
C12 C 0.1198(2) 0.5126(2) 0.92576(17) 0.0726(7) Uani 1 1 d . . . . .
H12 H 0.1305 0.4417 0.9522 0.087 Uiso 1 1 calc R U . . .
C18 C -0.0984(2) 0.7955(3) 0.55735(16) 0.0786(7) Uani 1 1 d . . . . .
H18 H -0.1699 0.7725 0.5191 0.094 Uiso 1 1 calc R U . . .
C22 C 0.2486(3) 0.5256(2) 0.51132(15) 0.0825(8) Uani 1 1 d . . . . .
C9 C 0.6048(2) 0.4791(2) 0.6901(2) 0.0867(8) Uani 1 1 d . . . . .
H9A H 0.6755 0.4423 0.6908 0.130 Uiso 1 1 calc R U . . .
H9B H 0.5527 0.4860 0.6332 0.130 Uiso 1 1 calc R U . . .
H9C H 0.5682 0.4345 0.7216 0.130 Uiso 1 1 calc R U . . .
C7 C 0.7588(2) 0.6043(4) 0.8357(2) 0.1067(11) Uani 1 1 d . . . . .
H7A H 0.7347 0.5562 0.8727 0.160 Uiso 1 1 calc R U . . .
H7B H 0.7807 0.6779 0.8611 0.160 Uiso 1 1 calc R U . . .
H7C H 0.8244 0.5702 0.8256 0.160 Uiso 1 1 calc R U . . .
C8 C 0.6818(3) 0.7192(3) 0.6704(2) 0.1020(10) Uani 1 1 d . . . . .
H8A H 0.6898 0.7943 0.6943 0.153 Uiso 1 1 calc R U . . .
H8B H 0.6235 0.7202 0.6155 0.153 Uiso 1 1 calc R U . . .
H8C H 0.7551 0.6954 0.6664 0.153 Uiso 1 1 calc R U . . .
F3B F 0.2141(8) 0.4599(8) 0.5397(5) 0.064(3) Uiso 0.193(6) 1 d . . P A 2
F1B F 0.3670(8) 0.4659(9) 0.5127(6) 0.085(3) Uiso 0.193(6) 1 d . . P A 2
F2B F 0.2564(12) 0.5738(12) 0.4337(9) 0.096(5) Uiso 0.193(6) 1 d . . P A 2
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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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 P1 C16 114.37(9) . . ?
O1 P1 C10 111.11(9) . . ?
C16 P1 C10 105.81(9) . . ?
O1 P1 C1 112.84(8) . . ?
C16 P1 C1 107.34(8) . . ?
C10 P1 C1 104.68(9) . . ?
O3 S1 O4 120.04(15) . . ?
O3 S1 O2 111.24(11) . . ?
O4 S1 O2 112.08(9) . . ?
O3 S1 C22 106.79(16) . . ?
O4 S1 C22 106.91(15) . . ?
O2 S1 C22 96.94(10) . . ?
C8 Si1 C9 112.56(16) . . ?
C8 Si1 C7 108.97(16) . . ?
C9 Si1 C7 107.32(16) . . ?
C8 Si1 C3 109.91(13) . . ?
C9 Si1 C3 111.83(10) . . ?
C7 Si1 C3 105.96(12) . . ?
C2 O2 S1 118.66(11) . . ?
C6 C1 C2 116.36(16) . . ?
C6 C1 P1 119.24(14) . . ?
C2 C1 P1 124.08(13) . . ?
C3 C2 C1 124.91(17) . . ?
C3 C2 O2 116.95(15) . . ?
C1 C2 O2 118.03(15) . . ?
C11 C10 C15 118.50(19) . . ?
C11 C10 P1 117.93(15) . . ?
C15 C10 P1 123.57(15) . . ?
C17 C16 C21 118.75(19) . . ?
C17 C16 P1 116.95(16) . . ?
C21 C16 P1 124.31(14) . . ?
C2 C3 C4 114.71(18) . . ?
C2 C3 Si1 128.43(15) . . ?
C4 C3 Si1 116.64(14) . . ?
C5 C6 C1 121.18(19) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C14 C15 C10 120.1(2) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
C20 C21 C16 120.2(2) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C12 C11 C10 120.8(2) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C18 C17 C16 120.6(2) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C14 C13 C12 119.9(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C5 C4 C3 122.56(19) . . ?
C5 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
C18 C19 C20 120.0(2) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C21 120.1(2) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C11 C12 C13 120.1(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
F1 C22 F2 113.5(3) . . ?
F1 C22 F3 107.2(4) . . ?
F2 C22 F3 100.3(3) . . ?
F3B C22 F2B 147.1(8) . . ?
F3B C22 F1B 99.8(7) . . ?
F2B C22 F1B 81.2(7) . . ?
F3B C22 S1 122.0(5) . . ?
F1 C22 S1 114.3(2) . . ?
F2 C22 S1 111.6(3) . . ?
F3 C22 S1 108.7(2) . . ?
F2B C22 S1 90.7(6) . . ?
F1B C22 S1 92.0(4) . . ?
Si1 C9 H9A 109.5 . . ?
Si1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Si1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Si1 C8 H8A 109.5 . . ?
Si1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
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
P1 O1 1.4750(14) . ?
P1 C16 1.800(2) . ?
P1 C10 1.812(2) . ?
P1 C1 1.8274(18) . ?
S1 O3 1.3969(19) . ?
S1 O4 1.4086(18) . ?
S1 O2 1.5664(13) . ?
S1 C22 1.827(3) . ?
Si1 C8 1.849(3) . ?
Si1 C9 1.856(3) . ?
Si1 C7 1.863(3) . ?
Si1 C3 1.907(2) . ?
O2 C2 1.440(2) . ?
F2 C22 1.276(3) . ?
C1 C6 1.390(3) . ?
C1 C2 1.397(2) . ?
C2 C3 1.384(2) . ?
C10 C11 1.387(3) . ?
C10 C15 1.388(3) . ?
C16 C17 1.386(3) . ?
C16 C21 1.390(3) . ?
C3 C4 1.404(3) . ?
C6 C5 1.372(3) . ?
C6 H6 0.9500 . ?
C15 C14 1.380(3) . ?
C15 H15 0.9500 . ?
C21 C20 1.382(3) . ?
C21 H21 0.9500 . ?
C14 C13 1.368(3) . ?
C14 H14 0.9500 . ?
C11 C12 1.372(3) . ?
C11 H11 0.9500 . ?
C17 C18 1.376(4) . ?
C17 H17 0.9500 . ?
C13 C12 1.374(4) . ?
C13 H13 0.9500 . ?
F3 C22 1.366(4) . ?
C4 C5 1.368(3) . ?
C4 H4 0.9500 . ?
C19 C18 1.367(4) . ?
C19 C20 1.378(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
F1 C22 1.237(3) . ?
C5 H5 0.9500 . ?
C12 H12 0.9500 . ?
C18 H18 0.9500 . ?
C22 F3B 1.090(9) . ?
C22 F2B 1.495(15) . ?
C22 F1B 1.630(10) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
