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_1568639
_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_formula_moiety         'C10 H13 P S'
_chemical_formula_sum            'C10 H13 P S'
_chemical_formula_weight         196.23
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-03
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2021.12.02 svn.rb8f36f48 for OlexSys, GUI svn.r6436)
;
_audit_update_record
;
2022-12-23 deposited with the CCDC.	2023-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.7780(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.77790(10)
_cell_length_b                   10.42680(10)
_cell_length_c                   11.69300(10)
_cell_measurement_reflns_used    26626
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      74.3240
_cell_measurement_theta_min      2.6770
_cell_volume                     2002.50(3)
_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      123.00(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 1.000
_diffrn_measured_fraction_theta_max 0.995
_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     67.00 111.00   0.50    0.10    --   77.75  20.00  27.23   88
  2  \w     93.00 118.00   0.50    0.10    --   77.75  36.00 108.98   50
  3  \w     86.00 114.00   0.50    0.10    --   77.75  20.00 156.30   56
  4  \w     92.00 117.00   0.50    0.10    --   77.75  23.00  52.65   50
  5  \w     59.00 100.00   0.50    0.10    --   62.55  15.00  60.00   82
  6  \w     54.00 104.00   0.50    0.10    --   77.75  17.00  -7.43  100
  7  \w     41.00  86.00   0.50    0.10    --   62.55  15.00  30.00   90
  8  \w     71.00  97.00   0.50    0.10    --   62.55  15.00 -30.00   52
  9  \w     61.00 106.00   0.50    0.10    --   77.75  17.00 -54.59   90
 10  \w     53.00 106.00   0.50    0.10    --   77.75  17.00-129.00  106
 11  \w     50.00  99.00   0.50    0.10    --   62.55  15.00-180.00   98
 12  \w     50.00 102.00   0.50    0.10    --   62.55  15.00 -60.00  104
 13  \w     50.00 113.00   0.50    0.10    --   77.75   5.00 -95.42  126
 14  \w     52.00  77.00   0.50    0.10    --   77.75   6.00  22.17   50
 15  \w     80.00 114.00   0.50    0.10    --   77.75   5.00 -63.14   68
 16  \w     81.00 115.00   0.50    0.10    --   77.75   6.00  22.17   68
 17  \w     61.00 114.00   0.50    0.10    --   77.75  13.00 148.39  106
 18  \w     72.00 116.00   0.50    0.10    --   77.75   9.00 112.42   88
 19  \w     78.00 106.00   0.50    0.10    --   77.75   4.00  89.37   56
 20  \w    -58.00 -27.00   0.50    0.10    --  -64.12 125.00  30.00   62
 21  \w    -61.00 -35.00   0.50    0.10    --  -74.00 117.00-170.08   52
 22  \w    -90.00 -42.00   0.50    0.10    --  -74.00 119.00 102.35   96
 23  \w     47.00  72.00   0.50    0.10    --   77.75 -82.00   7.83   50
 24  \w     39.00  65.00   0.50    0.10    --   77.75-130.00 135.71   52
 25  \w     60.00  97.00   0.50    0.10    --   77.75-162.00 128.33   74
 26  \w     77.00 104.00   0.50    0.10    --   77.75-130.00 135.71   54
 27  \w     46.00 108.00   0.50    0.10    --   77.75-140.00 -46.92  124
 28  \w     44.00 113.00   0.50    0.10    --   77.75-148.00 -77.92  138
 29  \w     44.00 111.00   0.50    0.10    --   77.75-141.00-173.78  134
 30  \w     42.00  68.00   0.50    0.10    --   75.18-125.00 -30.00   52
 31  \w     38.00  64.00   0.50    0.10    --   75.18-125.00   0.00   52
 32  \w     24.00  64.00   0.50    0.10    --   62.55-125.00 -60.00   80
 33  \w     37.00  63.00   0.50    0.10    --   75.18-125.00  30.00   52
 34  \w     45.00  97.00   0.50    0.10    --   75.18-125.00  90.00  104
 35  \w     40.00  78.00   0.50    0.10    --   75.18-125.00 120.00   76
 36  \w     25.00  63.00   0.50    0.10    --   62.55-125.00  90.00   76
 37  \w     38.00  73.00   0.50    0.10    --   75.18-125.00 150.00   70
 38  \w     60.00  97.00   0.50    0.10    --   75.18-125.00  60.00   74
 39  \w     73.00  98.00   0.50    0.10    --   77.75-117.00 -28.46   50
 40  \w     47.00  87.00   0.50    0.10    --   75.18-125.00 -90.00   80
 41  \w     24.00  83.00   0.50    0.10    --   62.55-125.00-180.00  118
 42  \w     38.00  92.00   0.50    0.10    --   75.18-125.00-150.00  108
 43  \w     50.00  75.00   0.50    0.10    --   77.75 -92.00  38.02   50
 44  \w     49.00  74.00   0.50    0.10    --   77.75 -84.00  45.09   50
 45  \w   -109.00 -63.00   0.50    0.10    --  -68.39 -15.00 120.00   92
 46  \w   -114.00 -88.00   0.50    0.10    --  -74.00 -33.00  67.96   52
 47  \w   -116.00 -91.00   0.50    0.10    --  -74.00 -34.00  51.41   50
 48  \w   -108.00 -56.00   0.50    0.10    --  -68.39 -15.00   0.00  104
 49  \w   -112.00 -86.00   0.50    0.10    --  -74.00 -31.00 -32.16   52
 50  \w   -114.00 -88.00   0.50    0.10    --  -74.00 -34.00-109.84   52
 51  \w   -113.00 -77.00   0.50    0.10    --  -74.00-126.00  -2.98   72
 52  \w   -112.00 -87.00   0.50    0.10    --  -74.00-112.00 140.81   50
 53  \w   -106.00 -81.00   0.50    0.10    --  -74.00 -91.00 138.96   50
;
_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      0.0923779000
_diffrn_orient_matrix_UB_12      -0.0091932000
_diffrn_orient_matrix_UB_13      0.0482257000
_diffrn_orient_matrix_UB_21      -0.0032975000
_diffrn_orient_matrix_UB_22      0.1242067000
_diffrn_orient_matrix_UB_23      0.0702508000
_diffrn_orient_matrix_UB_31      -0.0158195000
_diffrn_orient_matrix_UB_32      -0.0795527000
_diffrn_orient_matrix_UB_33      0.1041586000
_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  0.0226
_diffrn_reflns_av_unetI/netI     0.0094
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            34643
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.370
_diffrn_reflns_theta_min         2.690
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.898
_exptl_absorpt_correction_T_max  0.670
_exptl_absorpt_correction_T_min  0.170
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.83a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.302
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0272
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0414P)^2^+0.9270P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0751
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3934
_reflns_number_total             4062
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00580a2.cif
_cod_data_source_block           abs_ana_det_errooff
_cod_depositor_comments
'Adding full bibliography for 1568634--1568643.cif.'
_cod_database_code               1568639
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C10H13PS
_shelx_estimated_absorpt_t_max   0.860
_shelx_estimated_absorpt_t_min   0.442
_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:
 C11(H11A,H11B), C1(H1A,H1B), C20(H20A,H20B), C10(H10A,H10B), C18(H18A,H18B),
 C19(H19A,H19B), C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C13(H13), C3(H3), C14(H14), C17(H17), C16(H16), C15(H15), C5(H5),
 C6(H6), C4(H4)
;
_shelx_res_checksum              53623
_shelx_hkl_checksum              73554
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.565
_oxdiff_exptl_absorpt_empirical_full_min 0.463