Regioselective Phosphinylation of Coumarins under Green LED Irradiation and Mechanism Study
Li, Qingrui; Zhao, Xiuli; Li, Yabo; Huang, Mengmeng; Kim, Jung Keun; Wu, Yangjie; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB02478A

data_7155955
_publ_section_title
;
 Regioselective Phosphinylation of Coumarins under Green LED Irradiation
 and Mechanism Study
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB02478A
_journal_year                    2017
_chemical_formula_moiety         'C22 H17 O3 P'
_chemical_formula_sum            'C22 H17 O3 P'
_chemical_formula_weight         360.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-10-20
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2016-12-15 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.450(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6045(3)
_cell_length_b                   21.7424(7)
_cell_length_c                   10.3736(4)
_cell_measurement_reflns_used    2612
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4090
_cell_measurement_theta_min      4.9430
_cell_volume                     1829.97(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
  1 omega  -76.00  -47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   90.0000 29

  2 omega  -45.00  -19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -30.0000 26

  3 omega  -15.00   13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -30.0000 28

  4 omega -101.00  -64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  -30.0000 37

  5 omega    7.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  150.0000 48

  6 omega   59.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 33

  7 omega   61.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734 -160.0000  136.0000 51

  8 omega   34.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -150.0000 30

  9 omega  -32.00   16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -150.0000 48

 10 omega    9.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000    0.0000 93

 11 omega   45.00  100.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 55

 12 omega   44.00   70.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 26

 13 omega   79.00  173.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 94

 14 omega  100.00  174.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   90.0000 74

 15 omega  104.00  157.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 53

 16 omega   59.00   91.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 32

 17 omega   97.00  136.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 39

 18 omega   43.00   73.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 30

 19 omega   67.00  103.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 36

 20 omega  128.00  153.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0693635000
_diffrn_orient_matrix_UB_12      0.0623674000
_diffrn_orient_matrix_UB_13      -0.0640619000
_diffrn_orient_matrix_UB_21      -0.0877432000
_diffrn_orient_matrix_UB_22      -0.0320701000
_diffrn_orient_matrix_UB_23      -0.1375176000
_diffrn_orient_matrix_UB_31      -0.1534458000
_diffrn_orient_matrix_UB_32      -0.0098435000
_diffrn_orient_matrix_UB_33      0.0426333000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6869
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.798
_diffrn_reflns_theta_min         4.066
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.482
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3406
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0432
_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/[\s^2^(Fo^2^)+(0.0614P)^2^+0.3261P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1228
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2803
_reflns_number_total             3406
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02478a2.cif
_cod_data_source_block           201610158
_cod_original_cell_volume        1829.96(12)
_cod_database_code               7155955
_chemical_oxdiff_formula         C37H42N4O4
_reflns_odcompleteness_completeness 98.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
 C15-C14
 1.4 with sigma of 0.02
 C15A-C14A
 1.4 with sigma of 0.02
 C14A-C13A
 1.4 with sigma of 0.02
 C13-C14
 1.4 with sigma of 0.02
 C11-C16A
 1.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C16) = Uanis(C16A)
Uanis(C15) = Uanis(C15A)
Uanis(C12) = Uanis(C12A)
Uanis(C13) = Uanis(C13A)
Uanis(C14) = Uanis(C14A)
4. Others
 Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=
 Sof(H15A)=Sof(C16A)=Sof(H16A)=1-FVAR(1)
 Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=
 Sof(C16)=Sof(H16)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C9(H9), C12(H12), C12A(H12A), C13(H13), C13A(H13A),
 C14(H14), C14A(H14A), C15(H15), C15A(H15A), C16(H16), C16A(H16A), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22)
5.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              49059
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'