Novel synthetic route for (parent) phosphetanes, phospholanes, phosphinanes and phosphepanes.
Reichl, Stephan; Balázs, Gábor; Scheer, Manfred; Chemical science 14 (2023) 3834–3838; doi:10.1039/d3sc00580a

data_1568641
_publ_section_title
;
 Novel synthetic route for (parent) phosphetanes, phospholanes,
 phosphinanes and phosphepanes.
;
_journal_issue                   14
_journal_name_full               'Chemical science'
_journal_page_first              3834
_journal_page_last               3838
_journal_paper_doi               10.1039/d3sc00580a
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H15 P S'
_chemical_formula_sum            'C11 H15 P S'
_chemical_formula_weight         210.26
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-20
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-12-23 deposited with the CCDC.	2023-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0552(8)
_cell_length_b                   10.9392(5)
_cell_length_c                   6.2040(3)
_cell_measurement_reflns_used    4491
_cell_measurement_temperature    122.98(10)
_cell_measurement_theta_max      74.3450
_cell_measurement_theta_min      4.8380
_cell_volume                     1089.61(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.83a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.83a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.83a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      122.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     54.00 105.00   0.25    2.50    --   64.62-160.00  35.00  204
  2  \w     53.00  89.00   0.25    2.50    --   64.62 160.00  67.00  144
  3  \w    -97.00 -72.00   0.25    2.50    --  -66.78 160.00  67.00  100
  4  \w    -98.00 -73.00   0.25    2.50    --  -66.78-160.00  35.00  100
  5  \w    -90.00 -58.00   0.25    2.50    --  -67.46 118.00 -85.00  128
  6  \w     55.00  80.00   0.25    2.50    --   73.00-160.00  35.00  100
  7  \w     59.00  86.00   0.25    2.50    --   76.41-118.00-171.00  108
  8  \w     56.00  81.00   0.25    2.50    --   76.41 160.00  67.00  100
  9  \w    -86.00 -25.00   0.25    2.50    --  -66.78 125.00-180.00  244
 10  \w   -110.00 -40.00   0.25    2.50    --  -66.78 -15.00-150.00  280
 11  \w   -110.00 -49.00   0.25    2.50    --  -67.46 -15.00 150.00  244
 12  \w     41.00 103.00   0.25    2.50    --   76.41-125.00 -60.00  248
 13  \w     67.00  94.00   0.25    2.50    --   76.41-125.00  60.00  108
 14  \w     48.00 107.00   0.25    2.50    --   76.41  15.00   0.00  236
 15  \w     57.00 101.00   0.25    2.50    --   76.41-125.00 -90.00  176
 16  \w     53.00  86.00   0.25    2.50    --   76.41-125.00-150.00  132
 17  \w     42.00 102.00   0.25    2.50    --   76.41-125.00 -30.00  240
 18  \w     36.00  61.00   0.25    2.50    --   76.41-125.00  60.00  100
 19  \w     57.00 103.00   0.25    2.50    --   76.41-125.00-120.00  184
 20  \w     61.00  86.00   0.25    2.50    --   76.41  15.00-120.00  100
 21  \w     87.00 114.00   0.25    2.50    --   76.41  15.00-120.00  108
 22  \w     49.00 117.00   0.25    2.50    --   76.41  15.00  90.00  272
 23  \w     45.00  88.00   0.25    2.50    --   76.41-125.00  90.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0586998000
_diffrn_orient_matrix_UB_12      0.1111366000
_diffrn_orient_matrix_UB_13      -0.0146290000
_diffrn_orient_matrix_UB_21      -0.0750341000
_diffrn_orient_matrix_UB_22      -0.0864175000
_diffrn_orient_matrix_UB_23      -0.0273567000
_diffrn_orient_matrix_UB_31      -0.0118166000
_diffrn_orient_matrix_UB_32      -0.0029056000
_diffrn_orient_matrix_UB_33      0.2462906000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            8454
_diffrn_reflns_point_group_measured_fraction_full 0.835
_diffrn_reflns_point_group_measured_fraction_max 0.812
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.471
_diffrn_reflns_theta_min         4.892
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.615
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.671
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.83a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.282
_exptl_crystal_description       needle
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1811
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0514
_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^)+(0.1016P)^2^+0.3581P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1467
_reflns_Friedel_coverage         0.489
_reflns_Friedel_fraction_full    0.636
_reflns_Friedel_fraction_max     0.591
_reflns_number_gt                1706
_reflns_number_total             1811
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00580a2.cif
_cod_data_source_block           913_abs_gaus_nichtzentro
_cod_depositor_comments
'Adding full bibliography for 1568634--1568643.cif.'
_cod_database_code               1568641
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C11H15PS
_shelx_estimated_absorpt_t_max   0.899
_shelx_estimated_absorpt_t_min   0.503
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C1(H1A,H1B), C10(H10A,H10B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C6(H6), C5(H5)
;
_shelx_res_checksum              72573
_shelx_hkl_checksum              53722
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.170
_oxdiff_exptl_absorpt_empirical_full_min 0.539