#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:54:05 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180280 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/66/7116689.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_7116689
loop_
_publ_author_name
'Zhang, Hui-Jun'
'Lin, Weidong'
'Wu, Zhengjian'
'Ruan, Wenqing'
'Wen, Ting-Bin'
_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
_chemical_name_systematic
;
 ? 
;
_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       'ω 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/[σ²(Fo²)+(0.0500P)²+2.3050P] where P=(Fo²+2Fc²)/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
#BEGIN Tags that were not found in dictionaries:
_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'
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -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_calc_flag
_atom_site_refinement_flags_posn
P1 P 0.83703(5) 0.55109(3) 0.37910(2) 0.02511(15) Uani 1 d .
S1 S 0.65026(6) 0.56961(4) 0.48010(3) 0.04223(18) Uani 1 d .
O1 O 0.86829(14) 0.45661(10) 0.41705(7) 0.0383(4) Uani 1 d .
N1 N 0.67179(17) 0.71345(12) 0.39881(8) 0.0364(4) Uani 1 d .
C9 C 0.8221(3) 0.44419(19) 0.26564(13) 0.0613(7) Uani 1 d .
H9 H 0.8824 0.4017 0.2888 0.074 Uiso 1 calc R
C14 C 1.1833(2) 0.67908(17) 0.43100(11) 0.0445(5) Uani 1 d .
H14 H 1.2537 0.6660 0.4618 0.053 Uiso 1 calc R
C13 C 1.1859(2) 0.76153(17) 0.39008(11) 0.0455(6) Uani 1 d .
H13 H 1.2579 0.8038 0.3932 0.055 Uiso 1 calc R
C7 C 0.6908(4) 0.4843(4) 0.16778(15) 0.0928(14) Uani 1 d .
H7 H 0.6617 0.4688 0.1247 0.111 Uiso 1 calc R
C11 C 0.9749(2) 0.71846(15) 0.33910(10) 0.0369(5) Uani 1 d .
H11 H 0.9051 0.7316 0.3080 0.044 Uiso 1 calc R
C2 C 0.5607(2) 0.67675(17) 0.48568(10) 0.0423(5) Uani 1 d .
H2 H 0.5036 0.6873 0.5163 0.051 Uiso 1 calc R
C6 C 0.6441(3) 0.5677(3) 0.19557(14) 0.0940(13) Uani 1 d .
H6 H 0.5837 0.6092 0.1717 0.113 Uiso 1 calc R
C3 C 0.5839(2) 0.74409(16) 0.43968(10) 0.0401(5) Uani 1 d .
H3 H 0.5434 0.8074 0.4356 0.048 Uiso 1 calc R
C10 C 0.97261(17) 0.63541(13) 0.38041(8) 0.0250(4) Uani 1 d .
C1 C 0.71457(17) 0.62222(13) 0.41495(8) 0.0252(4) Uani 1 d .
C4 C 0.77529(19) 0.52873(15) 0.29543(9) 0.0334(4) Uani 1 d .
C12 C 1.0819(2) 0.78163(16) 0.34449(11) 0.0447(5) Uani 1 d .
H12 H 1.0836 0.8378 0.3172 0.054 Uiso 1 calc R
C8 C 0.7789(5) 0.4231(3) 0.20152(18) 0.0914(13) Uani 1 d .
H8 H 0.8106 0.3666 0.1814 0.110 Uiso 1 calc R
C5 C 0.6869(3) 0.5909(3) 0.26011(12) 0.0651(8) Uani 1 d .
H5 H 0.6557 0.6484 0.2793 0.078 Uiso 1 calc R
C15 C 1.07743(19) 0.61569(15) 0.42668(10) 0.0340(4) Uani 1 d .
H15 H 1.0760 0.5601 0.4545 0.041 Uiso 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 P1 C10 112.54(8)
O1 P1 C1 109.54(8)
O1 P1 C4 113.93(9)
C10 P1 C1 105.70(8)
C10 P1 C4 107.86(8)
C4 P1 C1 106.80(9)
C2 S1 C1 89.49(10)
C1 N1 C3 109.97(17)
C8 C9 C4 119.8(3)
C13 C14 C15 120.5(2)
C14 C13 C12 120.11(19)
C8 C7 C6 121.1(3)
C12 C11 C10 119.53(19)
C3 C2 S1 110.37(16)
C7 C6 C5 119.6(4)
C2 C3 N1 115.69(19)
C11 C10 P1 123.10(14)
C11 C10 C15 120.09(17)
C15 C10 P1 116.80(14)
S1 C1 P1 118.36(10)
N1 C1 P1 127.09(14)
N1 C1 S1 114.47(14)
C9 C4 P1 117.03(19)
C5 C4 P1 123.85(17)
C5 C4 C9 119.1(2)
C13 C12 C11 120.2(2)
C7 C8 C9 120.3(3)
C4 C5 C6 120.0(3)
C14 C15 C10 119.49(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O1 1.4820(14)
P1 C10 1.7930(17)
P1 C1 1.8107(19)
P1 C4 1.7995(19)
S1 C2 1.698(2)
S1 C1 1.7208(18)
N1 C3 1.379(3)
N1 C1 1.306(2)
C9 C4 1.385(3)
C9 C8 1.379(5)
C14 C13 1.375(3)
C14 C15 1.377(3)
C13 C12 1.376(3)
C7 C6 1.352(5)
C7 C8 1.351(6)
C11 C10 1.386(3)
C11 C12 1.384(3)
C2 C3 1.342(3)
C6 C5 1.392(4)
C10 C15 1.390(3)
C4 C5 1.374(3)
