#------------------------------------------------------------------------------
#$Date: 2019-11-08 04:03:03 +0200 (Fri, 08 Nov 2019) $
#$Revision: 225276 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/70/7157035.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_7157035
loop_
_publ_author_name
'Hou, Hong'
'Xu, Yue'
'Yang, Haibo'
'Yan, Chaoguo'
'Shi, Yaocheng'
'Zhu, Shaoqun'
_publ_section_title
;
 Regioselective radical arylation: silver-mediated synthesis of
 3-phosphorylated coumarins, quinolin-2(1H)-one and benzophosphole oxides.
;
_journal_issue                   35
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8175
_journal_page_last               8184
_journal_paper_doi               10.1039/c9ob01585j
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C31 H27 O3 P'
_chemical_formula_sum            'C31 H27 O3 P'
_chemical_formula_weight         478.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_date             2019-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-06-05 deposited with the CCDC.    2019-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.030(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.0617(8)
_cell_length_b                   13.6110(6)
_cell_length_c                   11.3034(6)
_cell_measurement_reflns_used    9136
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      2.40
_cell_volume                     2522.9(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.9960
_diffrn_measured_fraction_theta_max 0.9960
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25855
_diffrn_reflns_theta_full        27.5349
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0988 before and 0.0584 after correction.
The Ratio of minimum to maximum transmission is 0.8971.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.2598
_exptl_crystal_description       block
_exptl_crystal_F_000             1008.8721
_refine_diff_density_max         0.6012
_refine_diff_density_min         -0.4045
_refine_diff_density_rms         0.0844
_refine_ls_d_res_high            0.7687
_refine_ls_d_res_low             8.4908
_refine_ls_goodness_of_fit_ref   1.0516
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0516
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0565
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0750P)²+0.8790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1418
_refine_ls_wR_factor_ref         0.1596
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              21
_reflns_limit_h_min              -22
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3909
_reflns_number_total             5795
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9ob01585j2.cif
_cod_data_source_block           XY051302_sx
_cod_depositor_comments
'Adding full bibliography for 7157033--7157035.cif.'
_cod_database_code               7157035
_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:
 C6(H6), C19(H19), C16(H16), C9(H9), C8(H8), C15(H15), C21(H21), C28(H28),
 C25(H25), C27(H27), C18(H18), C24(H24), C30(H30), C29(H29), C23(H23), C22(H22),
  C17(H17), C31(H31)
2.b Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C11(H11a,H11b,H11c), C13(H13a,H13b,H13c)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 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_refinement_flags_posn
C5 C 0.63433(13) 0.56811(15) 0.4054(2) 0.0356(5) Uani 1.000000 .
C4 C 0.71355(12) 0.60338(15) 0.43088(19) 0.0339(5) Uani 1.000000 .
C3 C 0.77510(12) 0.56560(14) 0.53686(19) 0.0334(5) Uani 1.000000 .
C2 C 0.75225(12) 0.50022(15) 0.61324(19) 0.0332(5) Uani 1.000000 .
C6 C 0.57304(14) 0.59531(17) 0.3031(2) 0.0418(5) Uani 1.000000 .
H6 H 0.52115(14) 0.56860(17) 0.2898(2) 0.0502(6) Uiso 1.000000 R
C20 C 0.82836(14) 0.49125(17) 0.8784(2) 0.0431(5) Uani 1.000000 .
C19 C 0.90269(14) 0.58537(18) 0.4713(2) 0.0489(6) Uani 1.000000 .
H19 H 0.87907(14) 0.54821(18) 0.4015(2) 0.0586(7) Uiso 1.000000 R
C7 C 0.58856(14) 0.66230(17) 0.2202(2) 0.0420(5) Uani 1.000000 .
C16 C 0.97352(18) 0.6965(2) 0.6771(3) 0.0755(9) Uani 1.000000 .
H16 H 0.99753(18) 0.7343(2) 0.7461(3) 0.0906(11) Uiso 1.000000 R
C14 C 0.86016(13) 0.60254(16) 0.5581(2) 0.0383(5) Uani 1.000000 .
C9 C 0.72810(14) 0.67286(16) 0.3471(2) 0.0420(5) Uani 1.000000 .
H9 H 0.77978(14) 0.70026(16) 0.3609(2) 0.0504(6) Uiso 1.000000 R
C8 C 0.66752(14) 0.70074(17) 0.2457(2) 0.0464(6) Uani 1.000000 .
H8 H 0.67919(14) 0.74668(17) 0.1921(2) 0.0557(7) Uiso 1.000000 R
C15 C 0.89585(15) 0.65767(18) 0.6613(3) 0.0540(6) Uani 1.000000 .
H15 H 0.86809(15) 0.66885(18) 0.7202(3) 0.0647(8) Uiso 1.000000 R
C21 C 0.7690(2) 0.5505(2) 0.8987(3) 0.0708(9) Uani 1.000000 .
H21 H 0.7210(2) 0.5597(2) 0.8363(3) 0.0850(11) Uiso 1.000000 R
C28 C 0.7692(2) 0.1491(2) 0.6502(3) 0.0754(9) Uani 1.000000 .
H28 H 0.7765(2) 0.1054(2) 0.5907(3) 0.0905(11) Uiso 1.000000 R
C25 C 0.89796(17) 0.4722(3) 0.9762(3) 0.0793(10) Uani 1.000000 .
H25 H 0.93698(17) 0.4277(3) 0.9663(3) 0.0951(12) Uiso 1.000000 R
C27 C 0.79666(18) 0.24460(19) 0.6507(2) 0.0579(7) Uani 1.000000 .
H27 H 0.82371(18) 0.26416(19) 0.5936(2) 0.0694(8) Uiso 1.000000 R
C18 C 0.98044(16) 0.6238(2) 0.4891(3) 0.0660(8) Uani 1.000000 .
H18 H 1.00905(16) 0.6117(2) 0.4315(3) 0.0792(10) Uiso 1.000000 R
C10 C 0.52250(16) 0.6965(2) 0.1065(2) 0.0580(7) Uani 1.000000 .
C24 C 0.9082(2) 0.5205(4) 1.0883(3) 0.1006(13) Uani 1.000000 .
H24 H 0.9548(2) 0.5099(4) 1.1528(3) 0.1207(16) Uiso 1.000000 R
C30 C 0.71969(19) 0.1826(2) 0.8195(3) 0.0680(8) Uani 1.000000 .
H30 H 0.69371(19) 0.1619(2) 0.8775(3) 0.0816(10) Uiso 1.000000 R
C29 C 0.7321(2) 0.1180(2) 0.7347(3) 0.0667(8) Uani 1.000000 .
H29 H 0.7151(2) 0.0530(2) 0.7349(3) 0.0801(10) Uiso 1.000000 R
C23 C 0.8482(3) 0.5844(3) 1.1028(3) 0.0821(11) Uani 1.000000 .
H23 H 0.8557(3) 0.6187(3) 1.1763(3) 0.0985(13) Uiso 1.000000 R
C22 C 0.7791(3) 0.5972(2) 1.0110(3) 0.0859(11) Uani 1.000000 .
H22 H 0.7381(3) 0.6376(2) 1.0230(3) 0.1030(13) Uiso 1.000000 R
C12 C 0.5508(2) 0.6819(4) -0.0082(3) 0.1048(14) Uani 1.000000 .
H12a H 0.6006(11) 0.7175(19) 0.0000(13) 0.157(2) Uiso 1.000000 GR
H12b H 0.5600(18) 0.6132(4) -0.0185(16) 0.157(2) Uiso 1.000000 GR
H12c H 0.5097(9) 0.706(2) -0.0786(5) 0.157(2) Uiso 1.000000 GR
C1 C 0.66609(13) 0.47768(16) 0.5948(2) 0.0393(5) Uani 1.000000 .
O2 O 0.63766(10) 0.43647(14) 0.66734(17) 0.0579(5) Uani 1.000000 .
C26 C 0.78399(12) 0.31103(15) 0.73568(19) 0.0360(5) Uani 1.000000 .
C17 C 1.01489(18) 0.6789(2) 0.5900(4) 0.0759(9) Uani 1.000000 .
H17 H 1.06676(18) 0.7050(2) 0.6007(4) 0.0911(11) Uiso 1.000000 R
C31 C 0.74546(16) 0.27888(18) 0.8202(2) 0.0520(6) Uani 1.000000 .
H31 H 0.73661(16) 0.32240(18) 0.8786(2) 0.0623(7) Uiso 1.000000 R
O1 O 0.61223(9) 0.50485(11) 0.48576(14) 0.0436(4) Uani 1.000000 .
P1 P 0.82557(3) 0.43283(4) 0.73397(5) 0.03434(17) Uani 1.000000 .
O3 O 0.90644(9) 0.42708(12) 0.71123(15) 0.0463(4) Uani 1.000000 .
C11 C 0.44299(19) 0.6440(4) 0.0920(3) 0.1152(17) Uani 1.000000 .
H11a H 0.4493(6) 0.5758(7) 0.075(3) 0.173(3) Uiso 1.000000 GR
H11b H 0.4269(11) 0.650(2) 0.1666(12) 0.173(3) Uiso 1.000000 GR
H11c H 0.4019(5) 0.6727(18) 0.025(2) 0.173(3) Uiso 1.000000 GR
C13 C 0.5101(3) 0.8071(3) 0.1179(4) 0.1140(15) Uani 1.000000 .
H13a H 0.4844(18) 0.8190(3) 0.182(2) 0.171(2) Uiso 1.000000 GR
H13b H 0.5620(3) 0.8396(4) 0.137(3) 0.171(2) Uiso 1.000000 GR
H13c H 0.4762(16) 0.8319(5) 0.0414(10) 0.171(2) Uiso 1.000000 GR
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
P 0.10434 0.09671 6.43450 4.17910 1.78000 1.49080 1.90670 27.15700 0.52600
68.16450 1.11489999294
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C5 C4 123.43(19)
O1 C5 C4 120.53(18)
O1 C5 C6 116.01(18)
C3 C4 C5 119.33(18)
C9 C4 C5 115.81(19)
C9 C4 C3 124.83(19)
C2 C3 C4 118.91(18)
C14 C3 C4 117.61(18)
C14 C3 C2 123.46(19)
C1 C2 C3 119.83(18)
P1 C2 C3 122.87(15)
P1 C2 C1 117.19(15)
C7 C6 C5 120.1(2)
C25 C20 C21 118.9(2)
P1 C20 C21 125.3(2)
P1 C20 C25 115.8(2)
C18 C19 C14 119.9(3)
C8 C7 C6 117.4(2)
C10 C7 C6 122.3(2)
C10 C7 C8 120.2(2)
C17 C16 C15 119.9(3)
C19 C14 C3 120.2(2)
C15 C14 C3 120.1(2)
C15 C14 C19 119.5(2)
C8 C9 C4 121.1(2)
C9 C8 C7 122.0(2)
C14 C15 C16 119.8(3)
C22 C21 C20 121.0(3)
C29 C28 C27 121.1(3)
C24 C25 C20 119.6(3)
C26 C27 C28 120.1(3)
C17 C18 C19 120.3(3)
C12 C10 C7 110.1(2)
C11 C10 C7 112.4(2)
C11 C10 C12 109.7(3)
C13 C10 C7 108.4(3)
C13 C10 C12 106.6(3)
C13 C10 C11 109.6(3)
C23 C24 C25 119.4(3)
C31 C30 C29 120.4(3)
C30 C29 C28 119.3(3)
C22 C23 C24 120.4(3)
C23 C22 C21 120.4(3)
O2 C1 C2 125.6(2)
O1 C1 C2 118.11(18)
O1 C1 O2 116.33(19)
C31 C26 C27 118.2(2)
P1 C26 C27 117.19(18)
P1 C26 C31 124.43(17)
C18 C17 C16 120.5(3)
C26 C31 C30 120.8(2)
C1 O1 C5 121.62(16)
C20 P1 C2 107.26(10)
C26 P1 C2 106.23(9)
C26 P1 C20 107.88(10)
O3 P1 C2 112.21(9)
O3 P1 C20 112.90(10)
O3 P1 C26 110.04(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C5 C4 1.388(3)
C5 C6 1.378(3)
C5 O1 1.377(2)
C4 C3 1.452(3)
C4 C9 1.408(3)
C3 C2 1.369(3)
C3 C14 1.491(3)
C2 C1 1.459(3)
C2 P1 1.824(2)
C6 C7 1.385(3)
C20 C21 1.362(4)
C20 C25 1.405(4)
C20 P1 1.805(2)
C19 C14 1.391(3)
C19 C18 1.388(4)
C7 C8 1.399(3)
C7 C10 1.530(3)
C16 C15 1.392(4)
C16 C17 1.381(5)
C14 C15 1.379(3)
C9 C8 1.368(3)
C21 C22 1.387(4)
C28 C27 1.381(4)
C28 C29 1.353(4)
C25 C24 1.395(5)
C27 C26 1.379(3)
C18 C17 1.356(5)
C10 C12 1.515(4)
C10 C11 1.501(4)
C10 C13 1.531(5)
C24 C23 1.387(6)
C30 C29 1.360(4)
C30 C31 1.381(4)
C23 C22 1.350(5)
C1 O2 1.201(3)
C1 O1 1.369(3)
C26 C31 1.373(3)
C26 P1 1.805(2)
P1 O3 1.4738(15)
