#------------------------------------------------------------------------------
#$Date: 2017-05-05 04:14:37 +0300 (Fri, 05 May 2017) $
#$Revision: 196205 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/00/7120074.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_7120074
loop_
_publ_author_name
'Chen, Yuan-Hui'
'Xu, Xu-Long'
'Han, Fu-She'
_publ_section_title
;
 Efficient Synthesis of Cyclic P-Stereogenic Phosphinamides from Acyclic
 Chiral Precursors via Radical Oxidative Intramolecular Aryl C--H
 Phosphinamidation
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC02263H
_journal_year                    2017
_chemical_formula_sum            'C27 H19 F5 N O4 P'
_chemical_formula_weight         547.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-03-20 deposited with the CCDC.
2017-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                103.6640(10)
_cell_angle_beta                 110.7240(10)
_cell_angle_gamma                101.7210(10)
_cell_formula_units_Z            2
_cell_length_a                   9.8498(6)
_cell_length_b                   10.4837(7)
_cell_length_c                   13.4890(9)
_cell_measurement_reflns_used    2932
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      2.23
_cell_volume                     1201.25(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7554
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.080
_diffrn_reflns_theta_min         1.714
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         2.808
_refine_diff_density_min         -0.736
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4723
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1240
_refine_ls_R_factor_gt           0.1003
_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)+(0.2000P)²+1.9800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2948
_refine_ls_wR_factor_ref         0.3219
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3347
_reflns_number_total             4723
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7cc02263h2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'MULTI_SCAN' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7120074
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
C1 C 1.1704(8) 0.3169(7) 0.0673(7) 0.079(2) Uani 1 1 d . .
H1A H 1.1385 0.3979 0.0733 0.118 Uiso 1 1 calc R U
H1B H 1.2008 0.2998 0.0064 0.118 Uiso 1 1 calc R U
H1C H 1.2553 0.3310 0.1363 0.118 Uiso 1 1 calc R U
C2 C 0.9851(6) 0.2080(6) 0.1243(5) 0.0507(12) Uani 1 1 d . .
C3 C 1.0375(6) 0.3152(6) 0.2231(5) 0.0561(13) Uani 1 1 d . .
H3 H 1.1178 0.3931 0.2404 0.067 Uiso 1 1 calc R U
C4 C 0.9713(6) 0.3077(5) 0.2969(4) 0.0523(13) Uani 1 1 d . .
H4 H 1.0104 0.3808 0.3643 0.063 Uiso 1 1 calc R U
C5 C 0.8478(5) 0.1952(5) 0.2752(4) 0.0428(11) Uani 1 1 d . .
C6 C 0.7939(5) 0.0885(5) 0.1715(4) 0.0391(10) Uani 1 1 d . .
C7 C 0.8628(6) 0.0925(5) 0.0985(4) 0.0460(11) Uani 1 1 d . .
H7 H 0.8278 0.0185 0.0323 0.055 Uiso 1 1 calc R U
C8 C 0.7803(5) 0.1971(5) 0.3576(4) 0.0427(11) Uani 1 1 d . .
C9 C 0.7636(7) 0.3220(6) 0.4090(5) 0.0569(14) Uani 1 1 d . .
H9 H 0.7962 0.3989 0.3902 0.068 Uiso 1 1 calc R U
C10 C 0.7015(7) 0.3364(7) 0.4858(5) 0.0663(16) Uani 1 1 d . .
H10 H 0.6940 0.4216 0.5190 0.100 Uiso 1 1 calc DR U
C11 C 0.6497(7) 0.2217(7) 0.5137(4) 0.0614(15) Uani 1 1 d . U
C12 C 0.6692(6) 0.0995(6) 0.4666(4) 0.0533(13) Uani 1 1 d . .
H12 H 0.6379 0.0243 0.4876 0.064 Uiso 1 1 calc R U
C13 C 0.7333(5) 0.0817(5) 0.3892(4) 0.0439(11) Uani 1 1 d . .
C14 C 0.5506(14) 0.3638(12) 0.6243(10) 0.136(4) Uani 1 1 d . U
H14A H 0.4919 0.3866 0.5611 0.203 Uiso 1 1 calc DR U
H14B H 0.6441 0.4384 0.6711 0.203 Uiso 1 1 calc DR U
H14C H 0.4926 0.3490 0.6670 0.203 Uiso 1 1 calc R U
C15 C 0.7473(5) -0.0571(5) 0.3482(4) 0.0404(10) Uani 1 1 d . .
C16 C 0.8147(6) -0.1173(5) 0.4273(4) 0.0483(12) Uani 1 1 d . .
H16 H 0.8571 -0.0661 0.5035 0.058 Uiso 1 1 calc R U
C17 C 0.8196(7) -0.2503(5) 0.3947(5) 0.0561(14) Uani 1 1 d . .
H17 H 0.8659 -0.2871 0.4492 0.067 Uiso 1 1 calc R U
C18 C 0.7563(6) -0.3306(5) 0.2814(5) 0.0524(13) Uani 1 1 d . .
C19 C 0.6928(5) -0.2728(5) 0.2004(4) 0.0432(11) Uani 1 1 d . .
H19 H 0.6532 -0.3239 0.1243 0.052 Uiso 1 1 calc R U
C20 C 0.6890(5) -0.1364(5) 0.2345(4) 0.0379(10) Uani 1 1 d . .
C21 C 0.6955(9) -0.5498(8) 0.1439(6) 0.086(2) Uani 1 1 d . U
H21A H 0.5868 -0.5678 0.1136 0.128 Uiso 1 1 calc R U
H21B H 0.7177 -0.6354 0.1399 0.128 Uiso 1 1 calc R U
H21C H 0.7363 -0.5058 0.1011 0.128 Uiso 1 1 calc R U
C22 C 0.3847(5) -0.0402(5) 0.1732(4) 0.0421(11) Uani 1 1 d . .
C23 C 0.3389(6) 0.0558(6) 0.2310(4) 0.0515(13) Uani 1 1 d . .
C24 C 0.2285(7) 0.0186(8) 0.2688(5) 0.0649(17) Uani 1 1 d . .
C25 C 0.1590(7) -0.1165(8) 0.2490(5) 0.0688(18) Uani 1 1 d . .
C26 C 0.2010(6) -0.2148(7) 0.1917(5) 0.0631(15) Uani 1 1 d . .
C27 C 0.3115(6) -0.1785(6) 0.1525(4) 0.0499(12) Uani 1 1 d . .
F1 F 0.4037(4) 0.1918(4) 0.2523(3) 0.0671(9) Uani 1 1 d . .
F2 F 0.1920(5) 0.1187(5) 0.3286(4) 0.0930(14) Uani 1 1 d . .
F3 F 0.0525(5) -0.1515(6) 0.2852(4) 0.1040(16) Uani 1 1 d . .
F4 F 0.1310(5) -0.3477(5) 0.1683(5) 0.1025(15) Uani 1 1 d . .
F5 F 0.3445(4) -0.2783(3) 0.0928(3) 0.0682(10) Uani 1 1 d . .
N1 N 0.4954(4) 0.0031(4) 0.1363(3) 0.0420(9) Uani 1 1 d . .
H1 H 0.4928 0.0745 0.1156 0.050 Uiso 1 1 calc R U
O1 O 0.5945(4) -0.1579(3) 0.0137(3) 0.0434(8) Uani 1 1 d . .
O2 O 1.0457(5) 0.2000(4) 0.0462(4) 0.0697(12) Uani 1 1 d . .
O3 O 0.5868(9) 0.2342(8) 0.5831(6) 0.123(2) Uani 1 1 d . U
O4 O 0.7635(6) -0.4614(4) 0.2581(3) 0.0730(13) Uani 1 1 d . U
P1 P 0.63192(13) -0.06252(12) 0.12614(9) 0.0357(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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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
C3 C2 O2 125.7(5)
C3 C2 C7 119.5(5)
O2 C2 C7 114.8(5)
C2 C3 C4 120.0(5)
C3 C4 C5 123.0(5)
C4 C5 C6 115.5(4)
C4 C5 C8 119.6(4)
C6 C5 C8 124.8(4)
C7 C6 C5 122.0(4)
C7 C6 P1 115.8(4)
C5 C6 P1 122.2(4)
C6 C7 C2 119.9(5)
C9 C8 C13 117.7(5)
C9 C8 C5 117.7(5)
C13 C8 C5 124.6(4)
C10 C9 C8 123.1(6)
C9 C10 C11 119.3(5)
O3 C11 C12 122.4(7)
O3 C11 C10 119.2(6)
C12 C11 C10 118.4(5)
C11 C12 C13 123.7(5)
C12 C13 C8 117.7(5)
C12 C13 C15 116.4(5)
C8 C13 C15 125.9(4)
C20 C15 C16 117.2(4)
C20 C15 C13 124.0(4)
C16 C15 C13 118.6(4)
C17 C16 C15 121.5(5)
C16 C17 C18 120.9(5)
O4 C18 C19 124.4(5)
O4 C18 C17 116.4(4)
C19 C18 C17 119.1(5)
C18 C19 C20 119.5(4)
C15 C20 C19 121.6(4)
C15 C20 P1 121.6(4)
C19 C20 P1 116.1(3)
C23 C22 N1 119.8(5)
C23 C22 C27 116.4(5)
N1 C22 C27 123.8(4)
F1 C23 C22 119.4(5)
F1 C23 C24 118.4(5)
C22 C23 C24 122.3(6)
F2 C24 C25 119.8(6)
F2 C24 C23 119.4(6)
C25 C24 C23 120.8(6)
F3 C25 C24 120.4(7)
F3 C25 C26 120.9(7)
C24 C25 C26 118.7(5)
F4 C26 C25 119.7(6)
F4 C26 C27 119.2(6)
C25 C26 C27 121.0(6)
F5 C27 C22 120.1(5)
F5 C27 C26 119.0(5)
C22 C27 C26 120.8(5)
C22 N1 P1 129.6(3)
C2 O2 C1 117.4(5)
C11 O3 C14 121.9(7)
C18 O4 C21 118.9(5)
O1 P1 N1 115.3(2)
O1 P1 C20 113.1(2)
N1 P1 C20 108.1(2)
O1 P1 C6 112.3(2)
N1 P1 C6 103.5(2)
C20 P1 C6 103.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.437(7)
C2 C3 1.369(8)
C2 O2 1.379(6)
C2 C7 1.395(7)
C3 C4 1.377(8)
C4 C5 1.399(7)
C5 C6 1.408(7)
C5 C8 1.482(7)
C6 C7 1.384(7)
C6 P1 1.803(5)
C8 C9 1.402(7)
C8 C13 1.419(7)
C9 C10 1.372(8)
C10 C11 1.395(10)
C11 O3 1.290(8)
C11 C12 1.372(8)
C12 C13 1.396(7)
C13 C15 1.482(7)
C14 O3 1.504(12)
C15 C20 1.397(6)
C15 C16 1.401(6)
C16 C17 1.376(7)
C17 C18 1.392(8)
C18 O4 1.355(6)
C18 C19 1.391(7)
C19 C20 1.408(7)
C20 P1 1.784(4)
C21 O4 1.422(8)
C22 C23 1.374(7)
C22 N1 1.390(6)
C22 C27 1.394(7)
C23 F1 1.352(7)
C23 C24 1.382(8)
C24 F2 1.356(7)
C24 C25 1.359(10)
C25 F3 1.328(7)
C25 C26 1.361(9)
C26 F4 1.328(7)
C26 C27 1.394(8)
C27 F5 1.332(6)
N1 P1 1.662(4)
O1 P1 1.475(3)
