Synthesis of free and ligated 1,2-thiaphosphetanes – expanding the pool of strained P-ligands
Kyri, Andreas Wolfgang; Gleim, Florian; Becker, David; Schnakenburg, Gregor; Espinosa Ferao, Arturo; Streubel, Rainer; Chemical Communications  (2019) –; doi:10.1039/C8CC09892A

data_7122873
_publ_section_title
;
 Synthesis of free and ligated 1,2-thiaphosphetanes -- expanding the pool
 of strained P-ligands
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC09892A
_journal_year                    2019
_chemical_formula_moiety         'C22 H21 P S'
_chemical_formula_sum            'C22 H21 P S'
_chemical_formula_weight         348.42
_chemical_name_systematic        FLG-Thia
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2018-12-06 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9436(2)
_cell_length_b                   19.1201(5)
_cell_length_c                   10.6304(2)
_cell_measurement_reflns_used    9193
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.35
_cell_measurement_theta_min      4.63
_cell_volume                     1817.83(7)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon100 detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8-Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0743
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            28097
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.475
_diffrn_reflns_theta_max         67.475
_diffrn_reflns_theta_min         4.625
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.386
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.2059
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1804 before and 0.1170 after correction.
The Ratio of minimum to maximum transmission is 0.2732.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       plank
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.564
_refine_diff_density_min         -1.121
_refine_diff_density_rms         0.120
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.20(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3207
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0656
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1099P)^2^+1.5988P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1660
_refine_ls_wR_factor_ref         0.1670
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3158
_reflns_number_total             3207
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc09892a2.cif
_cod_data_source_block           cu_5486g
_cod_database_code               7122873
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.814
_shelx_estimated_absorpt_t_min   0.587
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.80(5)
 0.20(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
3. Uiso/Uaniso restraints and constraints
C2 \\sim C2S: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Sof(H1BC)=Sof(H1BD)=Sof(C2S)=Sof(H2S)=Sof(H3BD)=Sof(H3BE)=Sof(H3BF)=1-FVAR(1)
 Sof(H1AA)=Sof(H1AB)=Sof(C2)=Sof(H2)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C2(H2), C2S(H2S)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1AA,H1AB), C1(H1BC,H1BD)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
5.d Idealised Me refined as rotating group:
 C3(H3AA,H3AB,H3AC), C3(H3BD,H3BE,H3BF)
;
_shelx_res_checksum              12421
_olex2_submission_special_instructions 'No special instructions were received'