#------------------------------------------------------------------------------
#$Date: 2024-01-06 09:39:11 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288769 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/02/1570216.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_1570216
loop_
_publ_author_name
'Urvashi, ?'
'Mishra, Sampoorna'
'Patil, Nitin T.'
_publ_section_title
;
 Gold-catalyzed alkenylation and arylation of phosphorothioates.
;
_journal_issue                   45
_journal_name_full               'Chemical science'
_journal_page_first              13134
_journal_page_last               13139
_journal_paper_doi               10.1039/d3sc04888h
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C20 H16 Br O3 P S'
_chemical_formula_sum            'C20 H16 Br O3 P S'
_chemical_formula_weight         447.26
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-25
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-08-25 deposited with the CCDC.	2023-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.6150(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1164(2)
_cell_length_b                   8.8641(3)
_cell_length_c                   34.4839(11)
_cell_measurement_reflns_used    712
_cell_measurement_temperature    140.00
_cell_measurement_theta_max      78.29
_cell_measurement_theta_min      5.13
_cell_volume                     1869.48(11)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      140.00
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            11055
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        66.571
_diffrn_reflns_theta_max         66.571
_diffrn_reflns_theta_min         5.131
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.000
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_description       cubic
_exptl_crystal_F_000             904.0
_refine_diff_density_max         1.680
_refine_diff_density_min         -1.475
_refine_diff_density_rms         0.436
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.873
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.873
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0379
_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)+(0.1546P)²+11.0305P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1944
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2973
_reflns_number_total             3301
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc04888h2.cif
_cod_data_source_block           f1_a_CCDC1
_cod_depositor_comments
'Adding full bibliography for 1570215--1570216.cif.'
_cod_original_cell_volume        1869.49(11)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1570216
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Br01 Br 1.34461(8) 0.05859(6) 0.55750(2) 0.0322(3) Uani 1 1 d . . . . .
P002 P 0.36693(17) 0.39901(13) 0.35887(3) 0.0165(3) Uani 1 1 d . . . . .
S003 S 0.5047(2) 0.55861(12) 0.39493(3) 0.0240(3) Uani 1 1 d . . . . .
O004 O 0.1431(5) 0.4399(4) 0.34819(10) 0.0255(8) Uani 1 1 d . . . . .
O005 O 0.3985(5) 0.2455(3) 0.38153(8) 0.0197(7) Uani 1 1 d . . . . .
O006 O 0.5242(5) 0.3716(3) 0.32312(8) 0.0186(7) Uani 1 1 d . . . . .
C007 C 0.3708(7) 0.5027(5) 0.26752(12) 0.0182(9) Uani 1 1 d . . . . .
H007 H 0.236246 0.450591 0.270486 0.022 Uiso 1 1 calc R U . . .
C008 C 0.4013(8) 0.6045(5) 0.23692(13) 0.0219(9) Uani 1 1 d . . . . .
H008 H 0.285743 0.622840 0.218904 0.026 Uiso 1 1 calc R U . . .
C009 C 0.3364(7) 0.1066(5) 0.36458(12) 0.0183(9) Uani 1 1 d . . . . .
C00A C 1.1526(7) 0.1694(5) 0.52477(13) 0.0227(9) Uani 1 1 d . . . . .
C00B C 0.5424(7) 0.4805(5) 0.29316(11) 0.0162(8) Uani 1 1 d . . . . .
C00C C 1.2177(8) 0.2101(6) 0.48753(14) 0.0275(10) Uani 1 1 d . . . . .
H00C H 1.357017 0.180814 0.478240 0.033 Uiso 1 1 calc R U . . .
C00D C 0.8709(8) 0.3364(5) 0.47734(13) 0.0222(9) Uani 1 1 d . . . . .
C00E C 1.0779(8) 0.2932(6) 0.46440(13) 0.0261(10) Uani 1 1 d . . . . .
H00E H 1.122773 0.321816 0.439159 0.031 Uiso 1 1 calc R U . . .
C00F C 0.7420(8) 0.5548(5) 0.29008(14) 0.0212(10) Uani 1 1 d . . . . .
H00F H 0.856434 0.538447 0.308447 0.025 Uiso 1 1 calc R U . . .
C00G C 0.7680(8) 0.6535(5) 0.25932(14) 0.0242(10) Uani 1 1 d . . . . .
H00G H 0.903271 0.704594 0.256301 0.029 Uiso 1 1 calc R U . . .
C00H C 0.7240(8) 0.4556(5) 0.41639(14) 0.0230(10) Uani 1 1 d . . . . .
H00H H 0.847233 0.427344 0.401508 0.028 Uiso 1 1 calc R U . . .
C00I C 0.4870(8) 0.0276(6) 0.34328(14) 0.0240(10) Uani 1 1 d . . . . .
H00I H 0.628682 0.067447 0.338838 0.029 Uiso 1 1 calc R U . . .
C00J C 0.2193(9) -0.1708(5) 0.33508(15) 0.0310(11) Uani 1 1 d . . . . .
H00J H 0.178772 -0.266559 0.324925 0.037 Uiso 1 1 calc R U . . .
C00K C 0.7119(8) 0.4187(5) 0.45378(14) 0.0235(10) Uani 1 1 d . . . . .
H00K H 0.583251 0.449995 0.466700 0.028 Uiso 1 1 calc R U . . .
C00L C 0.5997(8) 0.6788(5) 0.23285(13) 0.0239(10) Uani 1 1 d . . . . .
H00L H 0.620143 0.746890 0.211932 0.029 Uiso 1 1 calc R U . . .
C00M C 0.8122(8) 0.2947(6) 0.51495(14) 0.0275(10) Uani 1 1 d . . . . .
H00M H 0.673486 0.324749 0.524399 0.033 Uiso 1 1 calc R U . . .
C00N C 0.9481(8) 0.2118(6) 0.53867(14) 0.0289(11) Uani 1 1 d . . . . .
H00N H 0.903953 0.183956 0.564012 0.035 Uiso 1 1 calc R U . . .
C00O C 0.1284(8) 0.0514(5) 0.37158(14) 0.0236(10) Uani 1 1 d . . . . .
H00O H 0.026588 0.108023 0.386248 0.028 Uiso 1 1 calc R U . . .
C00P C 0.4256(9) -0.1135(6) 0.32832(15) 0.0299(11) Uani 1 1 d . . . . .
H00P H 0.526502 -0.170002 0.313433 0.036 Uiso 1 1 calc R U . . .
C00Q C 0.0732(9) -0.0889(6) 0.35654(15) 0.0284(11) Uani 1 1 d . . . . .
H00Q H -0.068162 -0.129039 0.361165 0.034 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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
O004 P002 S003 111.02(16) . . ?
O004 P002 O005 116.62(19) . . ?
O004 P002 O006 114.57(18) . . ?
O005 P002 S003 104.24(12) . . ?
O005 P002 O006 100.37(16) . . ?
O006 P002 S003 109.04(13) . . ?
C00H S003 P002 101.56(16) . . ?
C009 O005 P002 121.0(3) . . ?
C00B O006 P002 120.9(3) . . ?
C008 C007 H007 121.1 . . ?
C00B C007 H007 121.1 . . ?
C00B C007 C008 117.9(4) . . ?
C007 C008 H008 119.9 . . ?
C00L C008 C007 120.3(4) . . ?
C00L C008 H008 119.9 . . ?
C00I C009 O005 119.1(4) . . ?
C00I C009 C00O 122.3(4) . . ?
C00O C009 O005 118.6(4) . . ?
C00C C00A Br01 120.1(4) . . ?
C00N C00A Br01 119.1(4) . . ?
C00N C00A C00C 120.8(4) . . ?
C007 C00B O006 119.9(4) . . ?
C007 C00B C00F 123.1(4) . . ?
C00F C00B O006 116.9(4) . . ?
C00A C00C H00C 120.3 . . ?
C00E C00C C00A 119.3(4) . . ?
C00E C00C H00C 120.3 . . ?
C00E C00D C00K 124.0(4) . . ?
C00M C00D C00E 117.7(4) . . ?
C00M C00D C00K 118.2(4) . . ?
C00C C00E C00D 121.3(4) . . ?
C00C C00E H00E 119.3 . . ?
C00D C00E H00E 119.3 . . ?
C00B C00F H00F 121.1 . . ?
C00G C00F C00B 117.7(4) . . ?
C00G C00F H00F 121.1 . . ?
C00F C00G H00G 119.5 . . ?
C00F C00G C00L 121.0(4) . . ?
C00L C00G H00G 119.5 . . ?
S003 C00H H00H 120.7 . . ?
C00K C00H S003 118.7(4) . . ?
C00K C00H H00H 120.7 . . ?
C009 C00I H00I 120.9 . . ?
C009 C00I C00P 118.2(5) . . ?
C00P C00I H00I 120.9 . . ?
C00P C00J H00J 120.1 . . ?
C00Q C00J H00J 120.1 . . ?
C00Q C00J C00P 119.8(5) . . ?
C00D C00K H00K 115.9 . . ?
C00H C00K C00D 128.2(5) . . ?
C00H C00K H00K 115.9 . . ?
C008 C00L H00L 120.0 . . ?
C00G C00L C008 120.0(4) . . ?
C00G C00L H00L 120.0 . . ?
C00D C00M H00M 118.9 . . ?
C00N C00M C00D 122.3(4) . . ?
C00N C00M H00M 118.9 . . ?
C00A C00N H00N 120.7 . . ?
C00M C00N C00A 118.6(4) . . ?
C00M C00N H00N 120.7 . . ?
C009 C00O H00O 120.9 . . ?
C009 C00O C00Q 118.1(5) . . ?
C00Q C00O H00O 120.9 . . ?
C00I C00P H00P 119.8 . . ?
C00J C00P C00I 120.5(5) . . ?
C00J C00P H00P 119.8 . . ?
C00J C00Q C00O 121.2(5) . . ?
C00J C00Q H00Q 119.4 . . ?
C00O C00Q H00Q 119.4 . . ?
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
Br01 C00A 1.895(5) . ?
P002 S003 2.0581(16) . ?
P002 O004 1.459(3) . ?
P002 O005 1.580(3) . ?
P002 O006 1.590(3) . ?
S003 C00H 1.777(5) . ?
O005 C009 1.413(5) . ?
O006 C00B 1.419(5) . ?
C007 H007 0.9500 . ?
C007 C008 1.403(6) . ?
C007 C00B 1.379(6) . ?
C008 H008 0.9500 . ?
C008 C00L 1.389(7) . ?
C009 C00I 1.376(7) . ?
C009 C00O 1.387(7) . ?
C00A C00C 1.396(7) . ?
C00A C00N 1.396(7) . ?
C00B C00F 1.392(7) . ?
C00C H00C 0.9500 . ?
C00C C00E 1.376(7) . ?
C00D C00E 1.400(7) . ?
C00D C00K 1.456(7) . ?
C00D C00M 1.399(6) . ?
C00E H00E 0.9500 . ?
C00F H00F 0.9500 . ?
C00F C00G 1.385(7) . ?
C00G H00G 0.9500 . ?
C00G C00L 1.386(7) . ?
C00H H00H 0.9500 . ?
C00H C00K 1.333(7) . ?
C00I H00I 0.9500 . ?
C00I C00P 1.402(8) . ?
C00J H00J 0.9500 . ?
C00J C00P 1.382(8) . ?
C00J C00Q 1.374(8) . ?
C00K H00K 0.9500 . ?
C00L H00L 0.9500 . ?
C00M H00M 0.9500 . ?
C00M C00N 1.373(7) . ?
C00N H00N 0.9500 . ?
C00O H00O 0.9500 . ?
C00O C00Q 1.388(7) . ?
C00P H00P 0.9500 . ?
C00Q H00Q 0.9500 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br01 C00A C00C C00E -178.7(4) . . . . ?
Br01 C00A C00N C00M 178.7(4) . . . . ?
P002 S003 C00H C00K -109.9(4) . . . . ?
P002 O005 C009 C00I 90.2(4) . . . . ?
P002 O005 C009 C00O -92.8(4) . . . . ?
P002 O006 C00B C007 -71.0(5) . . . . ?
P002 O006 C00B C00F 112.5(4) . . . . ?
S003 P002 O005 C009 -175.7(3) . . . . ?
S003 P002 O006 C00B -73.5(3) . . . . ?
S003 C00H C00K C00D -179.5(4) . . . . ?
O004 P002 O005 C009 61.5(4) . . . . ?
O004 P002 O006 C00B 51.6(4) . . . . ?
O005 P002 O006 C00B 177.3(3) . . . . ?
O005 C009 C00I C00P 176.9(4) . . . . ?
O005 C009 C00O C00Q -176.6(4) . . . . ?
O006 P002 O005 C009 -62.9(3) . . . . ?
O006 C00B C00F C00G 175.4(4) . . . . ?
C007 C008 C00L C00G -0.6(7) . . . . ?
C007 C00B C00F C00G -1.0(7) . . . . ?
C008 C007 C00B O006 -176.0(4) . . . . ?
C008 C007 C00B C00F 0.3(7) . . . . ?
C009 C00I C00P C00J -0.3(7) . . . . ?
C009 C00O C00Q C00J -0.4(7) . . . . ?
C00A C00C C00E C00D -0.6(8) . . . . ?
C00B C007 C008 C00L 0.5(7) . . . . ?
C00B C00F C00G C00L 0.9(7) . . . . ?
C00C C00A C00N C00M -0.1(8) . . . . ?
C00D C00M C00N C00A 0.7(8) . . . . ?
C00E C00D C00K C00H 6.0(8) . . . . ?
C00E C00D C00M C00N -1.2(8) . . . . ?
C00F C00G C00L C008 -0.1(7) . . . . ?
C00I C009 C00O C00Q 0.3(7) . . . . ?
C00K C00D C00E C00C -177.3(5) . . . . ?
C00K C00D C00M C00N 177.4(5) . . . . ?
C00M C00D C00E C00C 1.2(7) . . . . ?
C00M C00D C00K C00H -172.5(5) . . . . ?
C00N C00A C00C C00E 0.0(8) . . . . ?
C00O C009 C00I C00P 0.0(7) . . . . ?
C00P C00J C00Q C00O 0.2(8) . . . . ?
C00Q C00J C00P C00I 0.2(7) . . . . ?
