#------------------------------------------------------------------------------
#$Date: 2020-03-05 01:48:38 +0200 (Thu, 05 Mar 2020) $
#$Revision: 248867 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/27/1552772.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_1552772
loop_
_publ_author_name
'Zhu, Ren-Yi'
'Chen, Long'
'Hu, Xiao-Si'
'Zhou, Feng'
'Zhou, Jian'
_publ_section_title
;
 Enantioselective synthesis of P-chiral tertiary phosphine oxides
 with an ethynyl group via Cu(i)-catalyzed azide-alkyne
 cycloaddition.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              97
_journal_page_last               106
_journal_paper_doi               10.1039/c9sc04938j
_journal_volume                  11
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H13 O P'
_chemical_formula_weight         240.22
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-05-05 deposited with the CCDC.	2019-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6851(3)
_cell_length_b                   12.5057(5)
_cell_length_c                   13.9472(5)
_cell_measurement_reflns_used    7724
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.04
_cell_measurement_theta_min      2.19
_cell_volume                     1340.43(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15650
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.9532
_exptl_absorpt_correction_T_min  0.9128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.08(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0687P)²+0.0978P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0925
_reflns_number_gt                2246
_reflns_number_total             2362
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9sc04938j3.cif
_cod_data_source_block           z_CCDC2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 

 Adding full bibliography for 1552766--1552772.cif.

 Adding full bibliography for 1552766--1552772.cif.
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1552772
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P 0.16520(6) 0.94029(3) 0.40643(3) 0.04540(15) Uani 1 1 d .
O1 O 0.32355(18) 0.89755(12) 0.36009(10) 0.0664(4) Uani 1 1 d .
C1 C -0.0013(2) 0.98457(13) 0.32538(11) 0.0465(4) Uani 1 1 d .
C2 C 0.0365(3) 1.06207(15) 0.25589(13) 0.0538(4) Uani 1 1 d .
C3 C -0.0965(3) 1.09130(19) 0.19440(15) 0.0722(6) Uani 1 1 d .
H3A H -0.0741 1.1417 0.1469 0.087 Uiso 1 1 calc R
C4 C -0.2606(3) 1.0483(3) 0.20113(19) 0.0863(8) Uani 1 1 d .
H4A H -0.3470 1.0705 0.1589 0.104 Uiso 1 1 calc R
C5 C -0.2981(3) 0.9731(2) 0.26959(18) 0.0881(8) Uani 1 1 d .
H5A H -0.4091 0.9439 0.2741 0.106 Uiso 1 1 calc R
C6 C -0.1689(3) 0.94170(19) 0.33121(15) 0.0649(5) Uani 1 1 d .
H6A H -0.1932 0.8908 0.3779 0.078 Uiso 1 1 calc R
C7 C 0.2086(3) 1.04752(16) 0.48852(13) 0.0657(6) Uani 1 1 d .
C8 C 0.0771(5) 1.1033(2) 0.5302(2) 0.1009(10) Uani 1 1 d .
H8A H -0.0379 1.0892 0.5137 0.121 Uiso 1 1 calc R
C9 C 0.1154(9) 1.1815(3) 0.5977(3) 0.1507(19) Uani 1 1 d .
H9A H 0.0262 1.2204 0.6263 0.181 Uiso 1 1 calc R
C10 C 0.2826(10) 1.2008(3) 0.6216(3) 0.167(3) Uani 1 1 d .
H10A H 0.3074 1.2522 0.6679 0.200 Uiso 1 1 calc R
C11 C 0.4155(8) 1.1467(4) 0.5795(3) 0.156(2) Uani 1 1 d .
H11A H 0.5299 1.1629 0.5956 0.187 Uiso 1 1 calc R
C12 C 0.3815(5) 1.0678(3) 0.5127(2) 0.1052(11) Uani 1 1 d .
H12A H 0.4716 1.0292 0.4847 0.126 Uiso 1 1 calc R
C13 C 0.2136(3) 1.1102(2) 0.24516(17) 0.0792(7) Uani 1 1 d .
H13A H 0.2126 1.1609 0.1935 0.119 Uiso 1 1 calc R
H13B H 0.2965 1.0548 0.2315 0.119 Uiso 1 1 calc R
H13C H 0.2455 1.1457 0.3036 0.119 Uiso 1 1 calc R
C14 C 0.0645(3) 0.84348(14) 0.47946(13) 0.0500(4) Uani 1 1 d .
C15 C 0.0092(3) 0.77689(15) 0.53030(13) 0.0591(5) Uani 1 1 d .
H15A H -0.0363 0.7195 0.5685 0.089 Uiso 1 1 d R
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
O1 P1 C14 111.47(8)
O1 P1 C7 113.35(11)
C14 P1 C7 103.09(9)
O1 P1 C1 115.03(8)
C14 P1 C1 105.25(9)
C7 P1 C1 107.68(9)
C6 C1 C2 119.79(17)
C6 C1 P1 120.13(14)
C2 C1 P1 120.08(15)
C3 C2 C1 117.28(19)
C3 C2 C13 120.28(18)
C1 C2 C13 122.42(17)
C4 C3 C2 122.2(2)
C4 C3 H3A 118.9
C2 C3 H3A 118.9
C5 C4 C3 120.6(2)
C5 C4 H4A 119.7
C3 C4 H4A 119.7
C4 C5 C6 118.7(2)
C4 C5 H5A 120.6
C6 C5 H5A 120.6
C5 C6 C1 121.4(2)
C5 C6 H6A 119.3
C1 C6 H6A 119.3
C8 C7 C12 120.8(3)
C8 C7 P1 121.2(2)
C12 C7 P1 117.9(2)
C7 C8 C9 119.6(4)
C7 C8 H8A 120.2
C9 C8 H8A 120.2
C10 C9 C8 119.7(5)
C10 C9 H9A 120.1
C8 C9 H9A 120.1
C9 C10 C11 121.3(4)
C9 C10 H10A 119.4
C11 C10 H10A 119.4
C10 C11 C12 120.4(5)
C10 C11 H11A 119.8
C12 C11 H11A 119.8
C7 C12 C11 118.2(4)
C7 C12 H12A 120.9
C11 C12 H12A 120.9
C2 C13 H13A 109.5
C2 C13 H13B 109.5
H13A C13 H13B 109.5
C2 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C15 C14 P1 175.16(19)
C14 C15 H15A 176.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O1 1.4780(15)
P1 C14 1.7613(18)
P1 C7 1.794(2)
P1 C1 1.7950(18)
C1 C6 1.397(3)
C1 C2 1.401(2)
C2 C3 1.384(3)
C2 C13 1.496(3)
C3 C4 1.374(4)
C3 H3A 0.9300
C4 C5 1.372(4)
C4 H4A 0.9300
C5 C6 1.371(3)
C5 H5A 0.9300
C6 H6A 0.9300
C7 C8 1.359(4)
C7 C12 1.394(4)
C8 C9 1.389(5)
C8 H8A 0.9300
C9 C10 1.350(8)
C9 H9A 0.9300
C10 C11 1.359(8)
C10 H10A 0.9300
C11 C12 1.382(5)
C11 H11A 0.9300
C12 H12A 0.9300
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 C15 1.173(3)
C15 H15A 0.9600
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
O1 P1 C1 C6 123.55(17)
C14 P1 C1 C6 0.46(18)
C7 P1 C1 C6 -109.01(17)
O1 P1 C1 C2 -56.29(17)
C14 P1 C1 C2 -179.39(14)
C7 P1 C1 C2 71.15(17)
C6 C1 C2 C3 -1.1(3)
P1 C1 C2 C3 178.78(15)
C6 C1 C2 C13 -179.3(2)
P1 C1 C2 C13 0.6(3)
C1 C2 C3 C4 1.1(3)
C13 C2 C3 C4 179.4(3)
C2 C3 C4 C5 -0.6(4)
C3 C4 C5 C6 0.1(4)
C4 C5 C6 C1 -0.1(4)
C2 C1 C6 C5 0.6(3)
P1 C1 C6 C5 -179.25(19)
O1 P1 C7 C8 173.36(19)
C14 P1 C7 C8 -66.0(2)
C1 P1 C7 C8 45.0(2)
O1 P1 C7 C12 -10.4(2)
C14 P1 C7 C12 110.22(19)
C1 P1 C7 C12 -138.83(19)
C12 C7 C8 C9 0.1(4)
P1 C7 C8 C9 176.2(2)
C7 C8 C9 C10 -0.4(6)
C8 C9 C10 C11 1.4(7)
C9 C10 C11 C12 -2.0(7)
C8 C7 C12 C11 -0.7(4)
P1 C7 C12 C11 -176.9(2)
C10 C11 C12 C7 1.6(6)
O1 P1 C14 C15 41(2)
C7 P1 C14 C15 -81(2)
C1 P1 C14 C15 167(2)
