#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/30/1503057.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_1503057
loop_
_publ_author_name
'Zhang, Dong'
'Celaje, Jeff A.'
'Agua, Alon'
'Doan, Chad'
'Stewart, Timothy'
'Bau, Robert'
'Selke, Matthias'
_publ_section_title
;
 Photooxidation of mixed aryl and biarylphosphines.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3100
_journal_page_last               3103
_journal_paper_doi               10.1021/ol101122u
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C20 H19 O3 P'
_chemical_formula_weight         338.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.625(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.336(2)
_cell_length_b                   12.036(3)
_cell_length_c                   15.354(4)
_cell_measurement_reflns_used    4710
_cell_measurement_temperature    155(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.17
_cell_volume                     1689.9(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      155(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9821
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  0.9629
_exptl_absorpt_correction_T_min  0.9413
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Blessing,R.H.,Acta Crystallogr.1995,A51,33'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rombahedral
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0463
_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)+(0.0666P)²+0.3636P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1293
_reflns_number_gt                2918
_reflns_number_total             3803
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101122u_si_003.cif
_cod_data_source_block           po3m
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1503057
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P 0.79813(5) 0.78240(4) 0.06506(3) 0.03476(15) Uani 1 1 d .
O1 O 0.77731(16) 0.88380(11) 0.11644(8) 0.0495(4) Uani 1 1 d .
O2 O 0.78226(15) 0.63543(11) -0.09952(8) 0.0436(3) Uani 1 1 d .
O3 O 0.97103(15) 0.68994(13) 0.22729(8) 0.0505(4) Uani 1 1 d .
C1 C 0.67687(19) 0.78888(15) -0.04310(11) 0.0339(4) Uani 1 1 d .
C2 C 0.6843(2) 0.72057(14) -0.11589(11) 0.0360(4) Uani 1 1 d .
C3 C 0.5934(2) 0.74001(17) -0.19797(12) 0.0435(5) Uani 1 1 d .
H3 H 0.6007 0.6949 -0.2476 0.052 Uiso 1 1 calc R
C4 C 0.4927(2) 0.82491(19) -0.20701(13) 0.0504(5) Uani 1 1 d .
H4 H 0.4303 0.8373 -0.2632 0.060 Uiso 1 1 calc R
C5 C 0.4805(2) 0.89234(18) -0.13617(14) 0.0474(5) Uani 1 1 d .
H5 H 0.4096 0.9500 -0.1429 0.057 Uiso 1 1 calc R
C6 C 0.5734(2) 0.87437(16) -0.05515(13) 0.0398(4) Uani 1 1 d .
H6 H 0.5668 0.9214 -0.0064 0.048 Uiso 1 1 calc R
C7 C 0.8117(3) 0.57484(18) -0.17393(13) 0.0548(6) Uani 1 1 d .
H7A H 0.7261 0.5300 -0.1999 0.082 Uiso 1 1 calc R
H7B H 0.8960 0.5260 -0.1544 0.082 Uiso 1 1 calc R
H7C H 0.8333 0.6269 -0.2186 0.082 Uiso 1 1 calc R
C8 C 0.76149(19) 0.65501(15) 0.11791(11) 0.0364(4) Uani 1 1 d .
C9 C 0.8553(2) 0.62235(17) 0.19791(12) 0.0425(5) Uani 1 1 d .
C10 C 0.8272(3) 0.52589(19) 0.24090(14) 0.0529(5) Uani 1 1 d .
H10 H 0.8925 0.5020 0.2933 0.064 Uiso 1 1 calc R
C11 C 0.7028(3) 0.46461(19) 0.20671(15) 0.0581(6) Uani 1 1 d .
H11 H 0.6832 0.3987 0.2363 0.070 Uiso 1 1 calc R
C12 C 0.6073(2) 0.49731(19) 0.13074(14) 0.0534(5) Uani 1 1 d .
H12 H 0.5210 0.4557 0.1089 0.064 Uiso 1 1 calc R
C13 C 0.6386(2) 0.59176(17) 0.08642(12) 0.0442(5) Uani 1 1 d .
H13 H 0.5740 0.6135 0.0331 0.053 Uiso 1 1 calc R
C14 C 1.0628(3) 0.6666(2) 0.31193(13) 0.0588(6) Uani 1 1 d .
H14A H 1.0033 0.6645 0.3577 0.088 Uiso 1 1 calc R
H14B H 1.1372 0.7249 0.3265 0.088 Uiso 1 1 calc R
H14C H 1.1108 0.5946 0.3095 0.088 Uiso 1 1 calc R
C15 C 0.9838(2) 0.77127(15) 0.04836(11) 0.0354(4) Uani 1 1 d .
C16 C 1.0652(2) 0.86689(18) 0.05212(13) 0.0471(5) Uani 1 1 d .
H16 H 1.0222 0.9365 0.0608 0.057 Uiso 1 1 calc R
C17 C 1.2101(3) 0.8622(2) 0.04325(16) 0.0652(7) Uani 1 1 d .
H17 H 1.2655 0.9287 0.0452 0.078 Uiso 1 1 calc R
C18 C 1.2734(3) 0.7627(2) 0.03178(19) 0.0686(7) Uani 1 1 d .
H18 H 1.3732 0.7601 0.0270 0.082 Uiso 1 1 calc R
C19 C 1.1938(2) 0.6660(2) 0.02708(15) 0.0578(6) Uani 1 1 d .
H19 H 1.2379 0.5969 0.0182 0.069 Uiso 1 1 calc R
C20 C 1.0499(2) 0.66983(17) 0.03529(13) 0.0432(5) Uani 1 1 d .
H20 H 0.9948 0.6031 0.0321 0.052 Uiso 1 1 calc 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 C8 113.77(8)
O1 P1 C15 111.57(9)
C8 P1 C15 106.00(8)
O1 P1 C1 109.04(8)
C8 P1 C1 108.02(8)
C15 P1 C1 108.23(8)
C2 O2 C7 117.82(14)
C9 O3 C14 118.39(16)
C6 C1 C2 118.07(16)
C6 C1 P1 116.11(14)
C2 C1 P1 125.70(14)
O2 C2 C3 123.93(16)
O2 C2 C1 115.70(15)
C3 C2 C1 120.36(17)
C4 C3 C2 119.76(19)
C3 C4 C5 121.35(18)
C4 C5 C6 118.70(19)
C5 C6 C1 121.73(18)
C13 C8 C9 118.49(17)
C13 C8 P1 122.14(14)
C9 C8 P1 119.21(14)
O3 C9 C10 124.00(18)
O3 C9 C8 115.81(17)
C10 C9 C8 120.18(19)
C9 C10 C11 119.3(2)
C12 C11 C10 121.3(2)
C11 C12 C13 119.1(2)
C8 C13 C12 121.53(19)
C16 C15 C20 118.73(18)
C16 C15 P1 118.03(15)
C20 C15 P1 123.19(14)
C15 C16 C17 120.2(2)
C18 C17 C16 120.3(2)
C17 C18 C19 120.5(2)
C18 C19 C20 119.7(2)
C19 C20 C15 120.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O1 1.4871(14)
P1 C8 1.7996(18)
P1 C15 1.808(2)
P1 C1 1.8132(18)
O2 C2 1.363(2)
O2 C7 1.428(2)
O3 C9 1.355(2)
O3 C14 1.433(2)
C1 C6 1.398(3)
C1 C2 1.400(2)
C2 C3 1.390(3)
C3 C4 1.376(3)
C4 C5 1.380(3)
C5 C6 1.383(3)
C8 C13 1.380(3)
C8 C9 1.413(3)
C9 C10 1.387(3)
C10 C11 1.386(3)
C11 C12 1.375(3)
C12 C13 1.386(3)
C15 C16 1.374(3)
C15 C20 1.400(3)
C16 C17 1.388(3)
C17 C18 1.362(4)
C18 C19 1.374(4)
C19 C20 1.375(3)
