#------------------------------------------------------------------------------
#$Date: 2021-11-03 22:26:56 +0200 (Wed, 03 Nov 2021) $
#$Revision: 270233 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/90/4519094.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_4519094
loop_
_publ_author_name
'Song, Shu-Yong'
'Li, Yinwu'
'Ke, Zhuofeng'
'Xu, Senmiao'
_publ_section_title
;
 Iridium-Catalyzed Enantioselective C--H Borylation of Diarylphosphinates
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              13445
_journal_page_last               13451
_journal_paper_doi               10.1021/acscatal.1c03888
_journal_year                    2021
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C14 H12 N O2 P'
_chemical_formula_sum            'C14 H12 N O2 P'
_chemical_formula_weight         257.22
_chemical_name_systematic        C14H12NO2P
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-07-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4626(2)
_cell_length_b                   8.0078(2)
_cell_length_c                   21.1650(6)
_cell_measurement_reflns_used    7791
_cell_measurement_temperature    120.04
_cell_measurement_theta_max      68.24
_cell_measurement_theta_min      4.18
_cell_volume                     1264.80(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120.04
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0680
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7852
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.234
_diffrn_reflns_theta_min         4.177
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.875
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1141 before and 0.0904 after correction.
The Ratio of minimum to maximum transmission is 0.7672.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 902 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.118(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2272
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0371
_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)+(0.0566P)²+0.2545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.0980
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                2236
_reflns_number_total             2272
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c03888_si_002.cif
_cod_data_source_block           cu_b210717a_0m_a
_cod_database_code               4519094
_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.
;
_shelx_estimated_absorpt_t_max   0.865
_shelx_estimated_absorpt_t_min   0.766
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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'
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 0.43229(8) 0.26683(8) 0.65094(3) 0.0203(2) Uani 1 1 d . . . . .
O1 O 0.6178(2) 0.3408(2) 0.67384(9) 0.0259(4) Uani 1 1 d . . . . .
O2 O 0.4394(3) 0.1045(2) 0.61809(9) 0.0267(4) Uani 1 1 d . . . . .
N1 N 0.0897(4) 0.0928(3) 0.53060(13) 0.0365(6) Uani 1 1 d . . . . .
C1 C 0.3353(4) 0.4265(3) 0.60146(11) 0.0190(5) Uani 1 1 d . . . . .
C2 C 0.3814(4) 0.5944(3) 0.61128(12) 0.0235(6) Uani 1 1 d . . . . .
H2 H 0.463184 0.622460 0.644006 0.028 Uiso 1 1 calc R U . . .
C3 C 0.3096(4) 0.7199(3) 0.57406(13) 0.0258(6) Uani 1 1 d . . . . .
H3 H 0.342319 0.832916 0.581408 0.031 Uiso 1 1 calc R U . . .
C4 C 0.1901(4) 0.6812(3) 0.52611(12) 0.0261(6) Uani 1 1 d . . . . .
H4 H 0.142650 0.767565 0.500287 0.031 Uiso 1 1 calc R U . . .
C5 C 0.1395(4) 0.5166(3) 0.51570(12) 0.0252(6) Uani 1 1 d . . . . .
H5 H 0.056789 0.490393 0.483068 0.030 Uiso 1 1 calc R U . . .
C6 C 0.2110(3) 0.3896(3) 0.55350(12) 0.0208(5) Uani 1 1 d . . . . .
C7 C 0.1491(4) 0.2221(3) 0.54147(12) 0.0250(6) Uani 1 1 d . . . . .
C8 C 0.3050(3) 0.2673(3) 0.72253(12) 0.0214(5) Uani 1 1 d . . . . .
C9 C 0.1463(4) 0.1750(4) 0.72327(14) 0.0295(6) Uani 1 1 d . . . . .
H9 H 0.114145 0.108625 0.687825 0.035 Uiso 1 1 calc R U . . .
C10 C 0.0356(4) 0.1804(4) 0.77591(15) 0.0377(7) Uani 1 1 d . . . . .
H10 H -0.073018 0.118479 0.776411 0.045 Uiso 1 1 calc R U . . .
C11 C 0.0835(4) 0.2764(4) 0.82783(15) 0.0350(7) Uani 1 1 d . . . . .
H11 H 0.007057 0.280532 0.863677 0.042 Uiso 1 1 calc R U . . .
C12 C 0.2422(4) 0.3662(4) 0.82774(13) 0.0294(6) Uani 1 1 d . . . . .
H12 H 0.275244 0.430132 0.863714 0.035 Uiso 1 1 calc R U . . .
C13 C 0.3532(4) 0.3626(3) 0.77498(12) 0.0241(5) Uani 1 1 d . . . . .
H13 H 0.461477 0.424976 0.774670 0.029 Uiso 1 1 calc R U . . .
C14 C 0.7645(4) 0.3514(4) 0.62889(14) 0.0329(7) Uani 1 1 d . . . . .
H14A H 0.736945 0.436261 0.596986 0.049 Uiso 1 1 calc R U . . .
H14B H 0.780697 0.242889 0.608233 0.049 Uiso 1 1 calc R U . . .
H14C H 0.874871 0.382094 0.651136 0.049 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'
N N 0.0311 0.0180 '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'
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
O1 P1 C1 105.28(12) . . ?
O1 P1 C8 101.80(11) . . ?
O2 P1 O1 116.30(11) . . ?
O2 P1 C1 111.41(11) . . ?
O2 P1 C8 114.86(12) . . ?
C8 P1 C1 106.10(11) . . ?
C14 O1 P1 118.73(17) . . ?
C2 C1 P1 119.6(2) . . ?
C2 C1 C6 118.0(2) . . ?
C6 C1 P1 122.32(19) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.1(3) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.7(3) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C7 122.3(2) . . ?
C5 C6 C1 120.7(2) . . ?
C5 C6 C7 117.0(2) . . ?
N1 C7 C6 175.7(3) . . ?
C9 C8 P1 117.32(19) . . ?
C13 C8 P1 122.6(2) . . ?
C13 C8 C9 120.0(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C8 C13 H13 120.1 . . ?
C12 C13 C8 119.8(2) . . ?
C12 C13 H13 120.1 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 1.5818(19) . ?
P1 O2 1.4751(18) . ?
P1 C1 1.804(2) . ?
P1 C8 1.788(3) . ?
O1 C14 1.453(3) . ?
N1 C7 1.149(4) . ?
C1 C2 1.404(3) . ?
C1 C6 1.407(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.400(4) . ?
C6 C7 1.441(4) . ?
C8 C9 1.397(4) . ?
C8 C13 1.394(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(4) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
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
P1 C1 C2 C3 179.9(2) . . . . ?
P1 C1 C6 C5 -179.5(2) . . . . ?
P1 C1 C6 C7 1.5(4) . . . . ?
P1 C8 C9 C10 -175.4(2) . . . . ?
P1 C8 C13 C12 175.7(2) . . . . ?
O1 P1 C1 C2 -26.7(2) . . . . ?
O1 P1 C1 C6 154.6(2) . . . . ?
O1 P1 C8 C9 -165.9(2) . . . . ?
O1 P1 C8 C13 17.9(2) . . . . ?
O2 P1 O1 C14 50.8(2) . . . . ?
O2 P1 C1 C2 -153.6(2) . . . . ?
O2 P1 C1 C6 27.7(3) . . . . ?
O2 P1 C8 C9 -39.3(2) . . . . ?
O2 P1 C8 C13 144.5(2) . . . . ?
C1 P1 O1 C14 -73.1(2) . . . . ?
C1 P1 C8 C9 84.2(2) . . . . ?
C1 P1 C8 C13 -92.0(2) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C1 C6 C5 1.7(4) . . . . ?
C2 C1 C6 C7 -177.3(2) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
C4 C5 C6 C7 178.3(3) . . . . ?
C6 C1 C2 C3 -1.3(4) . . . . ?
C8 P1 O1 C14 176.37(19) . . . . ?
C8 P1 C1 C2 80.7(2) . . . . ?
C8 P1 C1 C6 -98.0(2) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C9 C8 C13 C12 -0.4(4) . . . . ?
C9 C10 C11 C12 -0.5(5) . . . . ?
C10 C11 C12 C13 1.0(4) . . . . ?
C11 C12 C13 C8 -0.6(4) . . . . ?
C13 C8 C9 C10 1.0(4) . . . . ?
