Stability and Reactivity of 1,3-Benzothiaphosphole: Metalation and Diels–Alder Chemistry
Worch, Joshua C.; Hellemann, Erich; Pros, Gabrielle; Gayathri, Chakicherla; Pintauer, Tomislav; Gil, Roberto R.; Noonan, Kevin J. T.; Organometallics 34 (2015) 5366–; doi:10.1021/acs.organomet.5b00583

data_4087762
_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       '\f and \w 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/[\s^2^(Fo^2^)+(0.1000P)^2^]
 where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_estimated_absorpt_t_min   0.484
_shelx_estimated_absorpt_t_max   0.864
_shelxl_version_number           2013-2
_shelx_res_checksum              92670
_shelx_hkl_checksum              48738