#------------------------------------------------------------------------------
#$Date: 2019-11-08 04:03:03 +0200 (Fri, 08 Nov 2019) $
#$Revision: 225276 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/70/7157034.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_7157034
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 H28 N O2 P'
_chemical_formula_sum            'C31 H28 N O2 P'
_chemical_formula_weight         477.55
_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_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             2019-06-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-06-10 deposited with the CCDC.    2019-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                89.785(5)
_cell_angle_beta                 77.673(5)
_cell_angle_gamma                69.240(4)
_cell_formula_units_Z            2
_cell_length_a                   10.4035(16)
_cell_length_b                   10.5900(16)
_cell_length_c                   13.0053(19)
_cell_measurement_reflns_used    4163
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      24.71
_cell_measurement_theta_min      2.37
_cell_volume                     1304.9(3)
_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 0.9906
_diffrn_measured_fraction_theta_max 0.9906
_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  0.0824
_diffrn_reflns_av_unetI/netI     0.1265
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20113
_diffrn_reflns_theta_full        27.5822
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1283 before and 0.0570 after correction.
The Ratio of minimum to maximum transmission is 0.9195.
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    1.2153
_exptl_crystal_description       block
_exptl_crystal_F_000             504.4163
_refine_diff_density_max         0.7975
_refine_diff_density_min         -0.6594
_refine_diff_density_rms         0.1590
_refine_ls_d_res_high            0.7675
_refine_ls_d_res_low             9.8717
_refine_ls_goodness_of_fit_ref   1.0676
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5999
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0676
_refine_ls_R_factor_all          0.1853
_refine_ls_R_factor_gt           0.0768
_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)+(0.0737P)²+0.0644P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1745
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2931
_reflns_number_total             5999
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9ob01585j2.cif
_cod_data_source_block           XY20190603111_sx
_cod_depositor_comments
'Adding full bibliography for 7157033--7157035.cif.'
_cod_database_code               7157034
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C25(H25), C27(H27), C29(H29), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C23(H23), C22(H22), C21(H21), C20(H20), C19(H19), N1(H1)
2.b Idealised Me refined as rotating group:
 C31(H31a,H31b,H31c), C11(H11a,H11b,H11c), C30(H30a,H30b,H30c), C10(H10a,H10b,
 H10c)
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -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_refinement_flags_posn
P1 P 0.37491(8) 0.33381(7) 0.74570(6) 0.0414(2) Uani 1.000000 .
O1 O 0.3023(2) 0.46662(18) 0.70754(15) 0.0570(6) Uani 1.000000 .
C4 C 0.4020(3) 0.2681(3) 0.9373(2) 0.0420(7) Uani 1.000000 .
N1 N 0.0802(2) 0.3423(2) 0.72089(18) 0.0507(6) Uani 1.000000 .
C5 C 0.4627(3) 0.3251(2) 0.8513(2) 0.0396(7) Uani 1.000000 .
C24 C 0.4955(3) 0.2137(3) 0.6401(2) 0.0399(7) Uani 1.000000 .
C3 C 0.2784(3) 0.2381(2) 0.9180(2) 0.0408(7) Uani 1.000000 .
C18 C -0.0258(3) 0.3541(3) 0.6654(2) 0.0513(8) Uani 1.000000 .
C2 C 0.2564(3) 0.2602(3) 0.8204(2) 0.0410(7) Uani 1.000000 .
C12 C 0.1816(3) 0.1994(3) 1.0031(2) 0.0423(7) Uani 1.000000 .
O2 O 0.1089(2) 0.1413(2) 0.79284(16) 0.0660(6) Uani 1.000000 .
C29 C 0.5029(3) 0.2507(3) 0.5380(2) 0.0526(8) Uani 1.000000 .
C17 C 0.0808(3) 0.2971(3) 1.0760(2) 0.0562(8) Uani 1.000000 .
C7 C 0.6356(3) 0.3431(3) 0.9402(2) 0.0496(8) Uani 1.000000 .
C27 C 0.6786(4) 0.0352(4) 0.4755(3) 0.0687(10) Uani 1.000000 .
C6 C 0.5782(3) 0.3612(3) 0.8520(2) 0.0471(7) Uani 1.000000 .
C28 C 0.5955(3) 0.1609(4) 0.4531(2) 0.0651(10) Uani 1.000000 .
C19 C -0.0677(3) 0.2489(3) 0.6446(2) 0.0597(9) Uani 1.000000 .
C20 C -0.1661(3) 0.2682(4) 0.5844(3) 0.0698(9) Uani 1.000000 .
C15 C 0.0016(4) 0.1308(4) 1.1636(3) 0.0806(11) Uani 1.000000 .
C16 C -0.0098(4) 0.2628(4) 1.1559(3) 0.0720(10) Uani 1.000000 .
C13 C 0.1870(4) 0.0684(3) 1.0104(3) 0.0795(11) Uani 1.000000 .
C21 C -0.2212(4) 0.3859(5) 0.5438(3) 0.0980(13) Uani 1.000000 .
C23 C -0.0851(4) 0.4754(4) 0.6271(4) 0.1054(15) Uani 1.000000 .
C31 C 0.6068(4) 0.2044(5) 0.3418(2) 0.1133(16) Uani 1.000000 .
C11 C 0.7607(3) 0.3819(3) 0.9439(3) 0.0714(10) Uani 1.000000 .
C14 C 0.0986(4) 0.0348(4) 1.0896(3) 0.0945(13) Uani 1.000000 .
C22 C -0.1840(6) 0.4920(5) 0.5675(4) 0.140(2) Uani 1.000000 .
C8 C 0.5759(3) 0.2865(3) 1.0240(2) 0.0563(8) Uani 1.000000 .
C9 C 0.4613(3) 0.2465(3) 1.0257(2) 0.0541(8) Uani 1.000000 .
C26 C 0.6754(4) -0.0056(3) 0.5769(3) 0.0636(9) Uani 1.000000 .
C30 C 0.7712(5) -0.1417(3) 0.5970(3) 0.1170(17) Uani 1.000000 .
C10 C 0.4116(4) 0.1800(4) 1.1212(3) 0.0958(13) Uani 1.000000 .
C25 C 0.5816(3) 0.0865(3) 0.6589(2) 0.0542(8) Uani 1.000000 .
C1 C 0.1415(3) 0.2408(3) 0.7786(2) 0.0433(7) Uani 1.000000 .
H6 H 0.6169(3) 0.3974(3) 0.7935(2) 0.0565(9) Uiso 1.000000 R
H8 H 0.6145(3) 0.2742(3) 1.0832(2) 0.0675(10) Uiso 1.000000 R
H25 H 0.5765(3) 0.0620(3) 0.7280(2) 0.0650(10) Uiso 1.000000 R
H27 H 0.7402(4) -0.0255(4) 0.4196(3) 0.0825(12) Uiso 1.000000 R
H29 H 0.4457(3) 0.3366(3) 0.5254(2) 0.0631(10) Uiso 1.000000 R
H13 H 0.2523(4) 0.0012(3) 0.9603(3) 0.0954(14) Uiso 1.000000 R
H14 H 0.1048(4) -0.0548(4) 1.0930(3) 0.1134(16) Uiso 1.000000 R
H15 H -0.0564(4) 0.1070(4) 1.2189(3) 0.0967(13) Uiso 1.000000 R
H16 H -0.0785(4) 0.3299(4) 1.2044(3) 0.0864(12) Uiso 1.000000 R
H17 H 0.0732(3) 0.3871(3) 1.0718(2) 0.0674(10) Uiso 1.000000 R
H23 H -0.0588(4) 0.5477(4) 0.6411(4) 0.1265(18) Uiso 1.000000 R
H22 H -0.2258(6) 0.5762(5) 0.5433(4) 0.168(3) Uiso 1.000000 R
H21 H -0.2837(4) 0.3956(5) 0.5002(3) 0.1176(16) Uiso 1.000000 R
H20 H -0.1950(3) 0.1972(4) 0.5716(3) 0.0837(11) Uiso 1.000000 R
H19 H -0.0297(3) 0.1654(3) 0.6710(2) 0.0717(10) Uiso 1.000000 R
H1 H 0.1100(2) 0.4086(2) 0.71763(18) 0.0609(8) Uiso 1.000000 R
H31a H 0.5139(4) 0.250(3) 0.3301(8) 0.170(2) Uiso 1.000000 GR
H31b H 0.658(3) 0.265(2) 0.3319(8) 0.170(2) Uiso 1.000000 GR
H31c H 0.655(3) 0.1261(6) 0.2925(2) 0.170(2) Uiso 1.000000 GR
H11a H 0.8462(3) 0.3061(7) 0.9169(15) 0.1071(15) Uiso 1.000000 GR
H11b H 0.7588(12) 0.4567(14) 0.9015(13) 0.1071(15) Uiso 1.000000 GR
H11c H 0.7567(12) 0.408(2) 1.0155(3) 0.1071(15) Uiso 1.000000 GR
H30a H 0.798(3) -0.2027(10) 0.5351(10) 0.175(2) Uiso 1.000000 GR
H30b H 0.8539(16) -0.1340(7) 0.613(2) 0.175(2) Uiso 1.000000 GR
H30c H 0.7230(12) -0.1759(15) 0.6552(17) 0.175(2) Uiso 1.000000 GR
H10a H 0.3283(17) 0.2445(8) 1.1656(11) 0.144(2) Uiso 1.000000 GR
H10b H 0.390(3) 0.1048(17) 1.0987(3) 0.144(2) Uiso 1.000000 GR
H10c H 0.4844(12) 0.148(2) 1.1599(12) 0.144(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'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'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
C5 P1 O1 120.14(12)
C24 P1 O1 112.19(12)
C24 P1 C5 107.79(12)
C2 P1 O1 113.73(12)
C2 P1 C5 91.93(12)
C2 P1 C24 109.14(12)
C3 C4 C5 112.2(2)
C9 C4 C5 118.6(3)
C9 C4 C3 129.2(3)
C1 N1 C18 128.9(2)
C4 C5 P1 110.2(2)
C6 C5 P1 127.7(2)
C6 C5 C4 122.1(3)
C29 C24 P1 118.7(2)
C25 C24 P1 121.7(2)
C25 C24 C29 119.6(3)
C2 C3 C4 114.0(2)
C12 C3 C4 122.4(2)
C12 C3 C2 123.3(3)
C19 C18 N1 123.9(3)
C23 C18 N1 117.3(3)
C23 C18 C19 118.7(3)
C3 C2 P1 111.4(2)
C1 C2 P1 122.0(2)
C1 C2 C3 126.3(3)
C17 C12 C3 119.8(3)
C13 C12 C3 122.2(3)
C13 C12 C17 117.9(3)
C28 C29 C24 120.8(3)
C16 C17 C12 120.5(3)
C11 C7 C6 121.1(3)
C8 C7 C6 117.9(3)
C8 C7 C11 121.0(3)
C26 C27 C28 123.4(3)
C7 C6 C5 119.7(3)
C27 C28 C29 117.6(3)
C31 C28 C29 120.4(4)
C31 C28 C27 122.0(3)
C20 C19 C18 119.6(3)
C21 C20 C19 121.8(3)
C14 C15 C16 119.2(3)
C15 C16 C17 120.2(3)
C14 C13 C12 121.4(3)
C22 C21 C20 118.8(3)
C22 C23 C18 120.4(3)
C13 C14 C15 120.7(3)
C23 C22 C21 120.6(4)
C9 C8 C7 124.2(3)
C8 C9 C4 117.5(3)
C10 C9 C4 124.3(3)
C10 C9 C8 118.2(3)
C30 C26 C27 121.2(3)
C25 C26 C27 117.1(3)
C25 C26 C30 121.7(3)
C26 C25 C24 121.4(3)
C2 C1 N1 113.5(2)
O2 C1 N1 123.6(3)
O2 C1 C2 122.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O1 1.4821(19)
P1 C5 1.790(3)
P1 C24 1.796(3)
P1 C2 1.798(3)
C4 C5 1.406(4)
C4 C3 1.499(4)
C4 C9 1.398(4)
N1 C18 1.412(3)
N1 C1 1.355(3)
C5 C6 1.385(4)
C24 C29 1.377(3)
C24 C25 1.383(4)
C3 C2 1.343(4)
C3 C12 1.490(4)
C18 C19 1.378(4)
C18 C23 1.358(4)
C2 C1 1.490(4)
C12 C17 1.372(4)
C12 C13 1.372(4)
O2 C1 1.219(3)
C29 C28 1.399(4)
C17 C16 1.386(4)
C7 C6 1.385(4)
C7 C11 1.507(4)
C7 C8 1.379(4)
C27 C28 1.376(4)
C27 C26 1.383(4)
C28 C31 1.511(4)
C19 C20 1.377(4)
C20 C21 1.333(4)
C15 C16 1.365(4)
C15 C14 1.358(5)
C13 C14 1.363(4)
C21 C22 1.367(5)
C23 C22 1.378(5)
C8 C9 1.395(4)
C9 C10 1.511(4)
C26 C30 1.493(4)
C26 C25 1.389(4)
