Silver-mediated direct phosphorylation of benzothiazoles and thiazoles with diarylphosphine oxides.
Zhang, Hui-Jun; Lin, Weidong; Wu, Zhengjian; Ruan, Wenqing; Wen, Ting-Bin; Chemical communications (Cambridge, England) 51 (2015) 3450–3453; doi:10.1039/c4cc10017d

data_7116689
_publ_section_title
;
 Silver-mediated direct phosphorylation of benzothiazoles and thiazoles
 with diarylphosphine oxides.
;
_journal_issue                   16
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3450
_journal_page_last               3453
_journal_paper_doi               10.1039/c4cc10017d
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C15 H12 N O P S'
_chemical_formula_sum            'C15 H12 N O P S'
_chemical_formula_weight         285.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-10-06
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2014-12-16 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.816(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.4363(4)
_cell_length_b                   13.1058(5)
_cell_length_c                   20.7087(8)
_cell_measurement_reflns_used    2719
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      27.1290
_cell_measurement_theta_min      3.6790
_cell_volume                     2812.44(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector_area_resol_mean 16.1903
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -39.00   50.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6309   57.0000  -30.0000 89

  2 omega  -42.00   49.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6309   57.0000   90.0000 91

  3 omega  -36.00   50.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6309   57.0000 -150.0000 86

  4 omega  -23.00   11.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6309  -77.0000   90.0000 34

  5 omega   54.00  104.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0372 -178.0000  120.0000 50

  6 omega   33.00   58.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0372   57.0000 -150.0000 25

  7 omega  -15.00   34.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0372   85.0000  -68.0000 49

  8 omega   11.00   37.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0372  -57.0000  -30.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0517973000
_diffrn_orient_matrix_UB_12      -0.0079838000
_diffrn_orient_matrix_UB_13      0.0187143000
_diffrn_orient_matrix_UB_21      -0.0294568000
_diffrn_orient_matrix_UB_22      -0.0336297000
_diffrn_orient_matrix_UB_23      -0.0241944000
_diffrn_orient_matrix_UB_31      0.0337048000
_diffrn_orient_matrix_UB_32      -0.0416392000
_diffrn_orient_matrix_UB_33      0.0159450000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10142
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.26
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
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    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+2.3050P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1026
_reflns_number_gt                2438
_reflns_number_total             2761
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc10017d2.cif
_cod_data_source_block           lwd2014100101
_cod_original_cell_volume        2812.44(18)
_cod_database_code               7116689
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C14(H14), C13(H13), C7(H7), C11(H11), C2(H2), C6(H6), C3(H3),
 C12(H12), C8(H8), C5(H5), C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'