#------------------------------------------------------------------------------
#$Date: 2019-11-24 06:42:13 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236992 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/77/4087762.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_4087762
loop_
_publ_author_name
'Worch, Joshua C.'
'Hellemann, Erich'
'Pros, Gabrielle'
'Gayathri, Chakicherla'
'Pintauer, Tomislav'
'Gil, Roberto R.'
'Noonan, Kevin J. T.'
_publ_section_title
;
 Stability and Reactivity of 1,3-Benzothiaphosphole: Metalation and
 Diels--Alder Chemistry
;
_journal_issue                   22
_journal_name_full               Organometallics
_journal_page_first              5366
_journal_paper_doi               10.1021/acs.organomet.5b00583
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C13 H15 P S2'
_chemical_formula_sum            'C13 H15 P S2'
_chemical_formula_weight         266.34
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 110.551(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7462(18)
_cell_length_b                   14.667(3)
_cell_length_c                   10.868(2)
_cell_measurement_reflns_used    9973
_cell_measurement_temperature    149(2)
_cell_measurement_theta_max      33.198
_cell_measurement_theta_min      2.436
_cell_volume                     1305.4(4)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2000)'
_computing_publication_material  'ORTEP-3 for Windows (Faruggia, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      149(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type  'Bruker Smart ApexII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17121
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.227
_diffrn_reflns_theta_min         2.436
_exptl_absorpt_coefficient_mu    0.500
_exptl_absorpt_correction_T_max  0.861
_exptl_absorpt_correction_T_min  0.502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rhomboid
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.475
_exptl_crystal_size_mid          0.302
_exptl_crystal_size_min          0.151
_exptl_transmission_factor_max   0.927
_exptl_transmission_factor_min   0.834
_refine_diff_density_max         0.705
_refine_diff_density_min         -0.922
_refine_diff_density_rms         0.231
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         4709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.1000P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1409
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4218
_reflns_number_total             4709
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om5b00583_si_002.cif
_cod_data_source_block           GP_KN_JLW1190_150K_0m
_cod_original_cell_volume        1305.5(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4087762
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.484
_shelx_estimated_absorpt_t_max   0.864
_shelxl_version_number           2013-2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
P1 P 0.05212(3) 0.11769(2) 0.18066(2) 0.01892(10) Uani 1 1 d . .
S2 S -0.11794(3) 0.15080(2) 0.01398(3) 0.02617(10) Uani 1 1 d . .
S1 S 0.24622(4) 0.26067(2) 0.36174(3) 0.03462(11) Uani 1 1 d . .
C6 C 0.25803(12) 0.13087(7) 0.18641(10) 0.01994(18) Uani 1 1 d . .
C1 C 0.34363(13) 0.20095(7) 0.26931(10) 0.0248(2) Uani 1 1 d . .
C5 C 0.33170(13) 0.08083(7) 0.11295(10) 0.0242(2) Uani 1 1 d . .
H5 H 0.2746 0.0322 0.0584 0.029 Uiso 1 1 calc R U
C4 C 0.48914(14) 0.10283(9) 0.12046(13) 0.0314(2) Uani 1 1 d . .
H4 H 0.5403 0.0695 0.0706 0.038 Uiso 1 1 calc R U
C2 C 0.50175(15) 0.22280(9) 0.27688(13) 0.0348(3) Uani 1 1 d . .
H2 H 0.5602 0.2704 0.3330 0.042 Uiso 1 1 calc R U
C3 C 0.57206(14) 0.17450(10) 0.20211(15) 0.0368(3) Uani 1 1 d . .
H3 H 0.6791 0.1900 0.2058 0.044 Uiso 1 1 calc R U
C11 C 0.03334(13) 0.00416(7) 0.24043(11) 0.0247(2) Uani 1 1 d . .
H11A H -0.0761 -0.0033 0.2470 0.030 Uiso 1 1 calc R U
H11B H 0.0455 -0.0420 0.1781 0.030 Uiso 1 1 calc R U
C10 C 0.16402(14) -0.00997(7) 0.37436(10) 0.0245(2) Uani 1 1 d . .
C7 C 0.06379(14) 0.19053(7) 0.32185(11) 0.0251(2) Uani 1 1 d . .
H7 H -0.0337 0.2315 0.2954 0.030 Uiso 1 1 calc R U
C9 C 0.17989(15) 0.05274(8) 0.46866(11) 0.0269(2) Uani 1 1 d . .
C8 C 0.06185(17) 0.13206(8) 0.43932(12) 0.0296(2) Uani 1 1 d . .
H8A H 0.0894 0.1713 0.5183 0.035 Uiso 1 1 calc R U
H8B H -0.0500 0.1083 0.4207 0.035 Uiso 1 1 calc R U
C13 C 0.26708(18) -0.09369(9) 0.38717(14) 0.0363(3) Uani 1 1 d . .
H13A H 0.3631 -0.0898 0.4679 0.054 Uiso 1 1 calc R U
H13B H 0.3024 -0.0982 0.3112 0.054 Uiso 1 1 calc R U
H13C H 0.2031 -0.1478 0.3908 0.054 Uiso 1 1 calc R U
C12 C 0.30704(18) 0.05146(11) 0.60388(12) 0.0393(3) Uani 1 1 d . .
H12A H 0.3715 -0.0046 0.6157 0.059 Uiso 1 1 calc R U
H12B H 0.2537 0.0538 0.6694 0.059 Uiso 1 1 calc R U
H12C H 0.3790 0.1044 0.6149 0.059 Uiso 1 1 calc R U
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'
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
C6 P1 C11 107.62(5)
C6 P1 C7 98.47(5)
C11 P1 C7 102.66(5)
C6 P1 S2 115.68(4)
C11 P1 S2 115.05(4)
C7 P1 S2 115.37(4)
C1 S1 C7 98.18(5)
C5 C6 C1 120.28(10)
C5 C6 P1 125.68(8)
C1 C6 P1 113.98(8)
C2 C1 C6 120.19(11)
C2 C1 S1 121.37(9)
C6 C1 S1 118.44(8)
C4 C5 C6 119.41(11)
C5 C4 C3 119.56(12)
C3 C2 C1 119.14(12)
C2 C3 C4 121.39(11)
C10 C11 P1 109.65(7)
C9 C10 C13 126.15(12)
C9 C10 C11 118.58(10)
C13 C10 C11 115.25(10)
C8 C7 S1 112.38(8)
C8 C7 P1 110.69(7)
S1 C7 P1 108.30(6)
C10 C9 C12 125.44(12)
C10 C9 C8 118.95(11)
C12 C9 C8 115.62(10)
C9 C8 C7 113.38(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C6 1.7905(11)
P1 C11 1.8156(11)
P1 C7 1.8430(11)
P1 S2 1.9590(5)
S1 C1 1.7616(12)
S1 C7 1.8183(12)
C6 C5 1.3973(15)
C6 C1 1.3982(14)
C1 C2 1.3936(16)
C5 C4 1.3885(15)
C4 C3 1.402(2)
C2 C3 1.375(2)
C11 C10 1.5167(16)
C10 C9 1.3474(15)
C10 C13 1.5006(16)
C7 C8 1.5429(16)
C9 C12 1.4998(17)
C9 C8 1.5133(17)
