Direct C4-H phosphonation of 8-hydroxyquinoline derivatives employing photoredox catalysis and silver catalysis.
Su, Xiaoxue; Yang, Fan; Wu, Yusheng; Wu, Yangjie; Organic & biomolecular chemistry 16 (2018) 2753–2756; doi:10.1039/c8ob00370j

data_7156177
_publ_section_title
;
 Direct C4-H phosphonation of 8-hydroxyquinoline derivatives employing
 photoredox catalysis and silver catalysis.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2753
_journal_page_last               2756
_journal_paper_doi               10.1039/c8ob00370j
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C28 H20 N O3 P, H2 O'
_chemical_formula_sum            'C28 H22 N O4 P'
_chemical_formula_weight         467.43
_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_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-26
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
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_audit_update_record
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2017-10-17 deposited with the CCDC.
2018-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.630(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3199(11)
_cell_length_b                   22.2918(14)
_cell_length_c                   9.1023(9)
_cell_measurement_reflns_used    2435
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.6150
_cell_measurement_theta_min      3.6040
_cell_volume                     2368.8(4)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_data_reduction
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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)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
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_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -44.00   -5.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.3317  -37.0000  -30.0000 39

  2 omega   -9.00   24.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.3317  -99.0000   90.0000 33

  3 omega  -22.00   53.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -99.0000  -90.0000 75

  4 omega    3.00   85.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661   57.0000    0.0000 82
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      0.0121020000
_diffrn_orient_matrix_UB_12      0.0151578000
_diffrn_orient_matrix_UB_13      -0.0615003000
_diffrn_orient_matrix_UB_21      0.0025759000
_diffrn_orient_matrix_UB_22      -0.0279021000
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_diffrn_orient_matrix_UB_31      -0.0594986000
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_diffrn_orient_matrix_UB_33      -0.0409534000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            10630
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         3.478
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95274
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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    1.311
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0532P)^2^+0.4939P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1371
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3181
_reflns_number_total             4823
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00370j3.cif
_cod_data_source_block           20170595
_cod_depositor_comments          'Adding full bibliography for 7156177.cif.'
_cod_database_code               7156177
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C38H70N2O2P1
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Riding coordinates:
 O4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C13(H13), C14(H14), C19(H19), C20(H20), C21(H21), C24(H24), C25(H25),
  C26(H26), C27(H27), C28(H28)
;
_olex2_submission_special_instructions 'No special instructions were received'