#------------------------------------------------------------------------------
#$Date: 2019-11-17 08:02:34 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228784 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/87/1548722.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_1548722
loop_
_publ_author_name
'Zhang, Kui'
'Cai, Lingchao'
'Yang, Zhongyue'
'Houk, K. N.'
'Kwon, Ohyun'
_publ_section_title
;
 Bridged [2.2.1] bicyclic phosphine oxide facilitates catalytic
 γ-umpolung addition-Wittig olefination.
;
_journal_issue                   7
_journal_name_full               'Chemical science'
_journal_page_first              1867
_journal_page_last               1872
_journal_paper_doi               10.1039/c7sc04381c
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C12 H15 O P'
_chemical_formula_sum            'C12 H15 O P'
_chemical_formula_weight         206.21
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2016-07-01 deposited with the CCDC.
2018-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6681(6)
_cell_length_b                   10.3977(7)
_cell_length_c                   11.4123(8)
_cell_measurement_reflns_used    9531
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.13
_cell_measurement_theta_min      3.87
_cell_volume                     1028.57(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.977
_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  0.0283
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9605
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.126
_diffrn_reflns_theta_min         5.756
_diffrn_source                   'I\mS micro--focus source'
_exptl_absorpt_coefficient_mu    2.050
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.53
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       rod
_exptl_crystal_F_000             440
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .4
_exptl_crystal_size_min          .2
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
; 
 Flack x determined using 787 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.032(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0252
_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)+(0.0331P)²+0.1696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0609
_refine_ls_wR_factor_ref         0.0612
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.964
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                1939
_reflns_number_total             1950
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7sc04381c2.cif
_cod_data_source_block           cu_kwon1503s_a
_cod_depositor_comments          'Adding full bibliography for 1548722.cif.'
_cod_database_code               1548722
_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. 
;
_shelxl_version_number           2014/6
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
P1 P 0.19864(5) 0.73343(4) 0.63559(3) 0.01211(14) Uani 1 1 d . .
O1 O 0.03490(14) 0.74523(13) 0.67535(11) 0.0183(3) Uani 1 1 d . .
C1 C 0.3460(2) 0.77732(18) 0.74278(16) 0.0163(4) Uani 1 1 d . .
H1 H 0.3742 0.7082 0.7999 0.020 Uiso 1 1 calc R U
C2 C 0.2932(2) 0.90554(18) 0.79784(16) 0.0201(4) Uani 1 1 d . .
H2A H 0.3572 0.9275 0.8668 0.024 Uiso 1 1 calc R U
H2B H 0.1837 0.9009 0.8222 0.024 Uiso 1 1 calc R U
C3 C 0.3154(3) 1.00591(17) 0.69813(18) 0.0218(4) Uani 1 1 d . .
H3A H 0.2152 1.0432 0.6741 0.026 Uiso 1 1 calc R U
H3B H 0.3847 1.0763 0.7236 0.026 Uiso 1 1 calc R U
C4 C 0.3887(2) 0.92819(18) 0.59659(18) 0.0200(4) Uani 1 1 d . .
H4 H 0.4557 0.9818 0.5446 0.024 Uiso 1 1 calc R U
C5 C 0.2639(2) 0.85308(18) 0.52859(17) 0.0177(4) Uani 1 1 d . .
H5A H 0.3079 0.8112 0.4582 0.021 Uiso 1 1 calc R U
H5B H 0.1783 0.9103 0.5045 0.021 Uiso 1 1 calc R U
C6 C 0.4785(2) 0.82323(19) 0.66221(17) 0.0193(4) Uani 1 1 d . .
H6A H 0.5664 0.8587 0.7072 0.023 Uiso 1 1 calc R U
H6B H 0.5151 0.7544 0.6092 0.023 Uiso 1 1 calc R U
C7 C 0.2404(2) 0.57121(17) 0.58684(16) 0.0138(4) Uani 1 1 d . .
C8 C 0.3391(2) 0.54053(19) 0.49456(16) 0.0163(4) Uani 1 1 d . .
H8 H 0.3864 0.6070 0.4502 0.020 Uiso 1 1 calc R U
C9 C 0.3682(2) 0.41193(19) 0.46759(17) 0.0199(4) Uani 1 1 d . .
H9 H 0.4359 0.3909 0.4050 0.024 Uiso 1 1 calc R U
C10 C 0.2985(3) 0.31436(18) 0.53210(16) 0.0202(4) Uani 1 1 d . .
H10 H 0.3201 0.2270 0.5142 0.024 Uiso 1 1 calc R U
C11 C 0.1976(2) 0.34431(17) 0.62252(15) 0.0189(4) Uani 1 1 d . .
H11 H 0.1488 0.2776 0.6657 0.023 Uiso 1 1 calc R U
C12 C 0.1683(2) 0.47249(18) 0.64958(16) 0.0158(4) Uani 1 1 d . .
H12 H 0.0989 0.4931 0.7111 0.019 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'
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
O1 P1 C7 111.05(8)
O1 P1 C1 116.11(8)
C7 P1 C1 107.35(8)
O1 P1 C5 116.09(8)
C7 P1 C5 111.44(9)
C1 P1 C5 93.48(9)
C2 C1 C6 101.29(15)
C2 C1 P1 106.32(12)
C6 C1 P1 101.44(12)
C2 C1 H1 115.3
C6 C1 H1 115.3
P1 C1 H1 115.3
C1 C2 C3 104.18(15)
C1 C2 H2A 110.9
C3 C2 H2A 110.9
C1 C2 H2B 110.9
C3 C2 H2B 110.9
H2A C2 H2B 108.9
C4 C3 C2 104.36(15)
C4 C3 H3A 110.9
C2 C3 H3A 110.9
C4 C3 H3B 110.9
C2 C3 H3B 110.9
H3A C3 H3B 108.9
C6 C4 C5 103.94(15)
C6 C4 C3 102.35(16)
C5 C4 C3 110.66(16)
C6 C4 H4 113.0
C5 C4 H4 113.0
C3 C4 H4 113.0
C4 C5 P1 103.00(13)
C4 C5 H5A 111.2
P1 C5 H5A 111.2
C4 C5 H5B 111.2
P1 C5 H5B 111.2
H5A C5 H5B 109.1
C4 C6 C1 97.63(14)
C4 C6 H6A 112.2
C1 C6 H6A 112.2
C4 C6 H6B 112.2
C1 C6 H6B 112.2
H6A C6 H6B 109.8
C8 C7 C12 119.54(17)
C8 C7 P1 124.57(15)
C12 C7 P1 115.88(14)
C7 C8 C9 119.81(18)
C7 C8 H8 120.1
C9 C8 H8 120.1
C10 C9 C8 120.23(18)
C10 C9 H9 119.9
C8 C9 H9 119.9
C11 C10 C9 120.22(17)
C11 C10 H10 119.9
C9 C10 H10 119.9
C10 C11 C12 119.66(17)
C10 C11 H11 120.2
C12 C11 H11 120.2
C11 C12 C7 120.52(18)
C11 C12 H12 119.7
C7 C12 H12 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O1 1.4951(13)
P1 C7 1.8127(19)
P1 C1 1.8266(18)
P1 C5 1.8328(19)
C1 C2 1.543(2)
C1 C6 1.547(3)
C1 H1 1.0000
C2 C3 1.556(3)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.549(3)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C6 1.535(3)
C4 C5 1.543(3)
C4 H4 1.0000
C5 H5A 0.9900
C5 H5B 0.9900
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.394(3)
C7 C12 1.399(3)
C8 C9 1.395(3)
C8 H8 0.9500
C9 C10 1.392(3)
C9 H9 0.9500
C10 C11 1.388(3)
C10 H10 0.9500
C11 C12 1.391(3)
C11 H11 0.9500
C12 H12 0.9500
