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_1568642
_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         'C13 H19 P S'
_chemical_formula_sum            'C13 H19 P S'
_chemical_formula_weight         238.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-21
_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                 94.2160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.92590(10)
_cell_length_b                   9.99760(10)
_cell_length_c                   19.73260(10)
_cell_measurement_reflns_used    36019
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      74.4740
_cell_measurement_theta_min      3.3710
_cell_volume                     2543.10(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(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 0.994
_diffrn_measured_fraction_theta_max 0.983
_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     48.00 120.00   0.50    0.45    --   76.70  15.00 150.00  144
  2  \w     73.00 116.00   0.50    0.45    --   76.70  15.00  60.00   86
  3  \w     63.00 120.00   0.50    0.45    --   77.25  21.00   3.44  114
  4  \w     48.00  73.00   0.50    0.45    --   76.70  15.00 -60.00   50
  5  \w     53.00 119.00   0.50    0.45    --   77.25  17.00-157.77  132
  6  \w     37.00  95.00   0.50    0.45    --   64.79  15.00-180.00  116
  7  \w     47.00  76.00   0.50    0.45    --   76.70   0.00 -60.00   58
  8  \w     77.00 111.00   0.50    0.45    --   76.70   0.00  90.00   68
  9  \w     43.00  72.00   0.50    0.45    --   76.70   0.00  90.00   58
 10  \w    -93.00 -49.00   0.50    0.45    --  -67.57 125.00 -60.00   88
 11  \w    -86.00 -61.00   0.50    0.45    --  -66.86 135.00  -5.00   50
 12  \w    -87.00 -62.00   0.50    0.45    --  -67.57 135.00  -5.00   50
 13  \w    -94.00 -32.00   0.50    0.45    --  -67.57 125.00  30.00  124
 14  \w    -93.00 -29.00   0.50    0.45    --  -66.86 125.00  60.00  128
 15  \w    -76.00 -50.00   0.50    0.45    --  -67.57 135.00 174.00   52
 16  \w    -96.00 -70.00   0.50    0.45    --  -66.86 135.00 174.00   52
 17  \w    -92.00 -29.00   0.50    0.45    --  -66.86 125.00 120.00  126
 18  \w    -94.00 -68.00   0.50    0.45    --  -67.57 125.00 -30.00   52
 19  \w    -63.00 -38.00   0.50    0.45    --  -67.57 125.00 -30.00   50
 20  \w    -93.00 -34.00   0.50    0.45    --  -67.57 125.00-120.00  118
 21  \w    -61.00 -36.00   0.50    0.45    --  -73.25  59.00 -12.37   50
 22  \w    -58.00 -33.00   0.50    0.45    --  -73.25  53.00  27.55   50
 23  \w   -100.00 -35.00   0.50    0.45    --  -66.86   0.00   0.00  130
 24  \w   -101.00 -35.00   0.50    0.45    --  -67.57   0.00-180.00  132
 25  \w    -96.00 -34.00   0.50    0.45    --  -66.86   0.00 -90.00  124
 26  \w   -109.00 -78.00   0.50    0.45    --  -67.57 -15.00 -90.00   62
 27  \w   -118.00 -93.00   0.50    0.45    --  -73.25 -32.00 126.19   50
 28  \w     36.00  61.00   0.50    0.45    --   64.79-135.00 108.00   50
 29  \w     77.00 103.00   0.50    0.45    --   72.89-135.00 108.00   52
 30  \w     65.00  91.00   0.50    0.45    --   76.70-135.00 108.00   52
 31  \w     74.00  99.00   0.50    0.45    --   72.89-125.00  30.00   50
 32  \w     36.00  61.00   0.50    0.45    --   64.79-135.00 -71.00   50
 33  \w     28.00  54.00   0.50    0.45    --   64.79-125.00 -60.00   52
 34  \w     31.00  57.00   0.50    0.45    --   72.89-125.00 -30.00   52
 35  \w     32.00  58.00   0.50    0.45    --   72.89-125.00  30.00   52
 36  \w     73.00  99.00   0.50    0.45    --   72.89-125.00 -30.00   52
 37  \w     78.00 103.00   0.50    0.45    --   76.70-125.00 -30.00   50
 38  \w     60.00  85.00   0.50    0.45    --   76.70-135.00 -71.00   50
 39  \w     74.00  99.00   0.50    0.45    --   72.89-125.00-180.00   50
 40  \w     41.00 104.00   0.50    0.45    --   72.89-135.00 -71.00  126
 41  \w     43.00 103.00   0.50    0.45    --   76.70-125.00 -60.00  120
 42  \w     35.00  72.00   0.50    0.45    --   76.70-125.00 -30.00   74
 43  \w     70.00 102.00   0.50    0.45    --   76.70-125.00 -90.00   64
 44  \w     35.00 103.00   0.50    0.45    --   76.70-125.00  30.00  136
 45  \w     36.00 103.00   0.50    0.45    --   76.70-125.00  90.00  134
 46  \w     43.00 103.00   0.50    0.45    --   76.70-125.00 150.00  120
 47  \w     36.00 100.00   0.50    0.45    --   76.70-125.00 120.00  128
 48  \w     58.00  99.00   0.50    0.45    --   76.70-125.00  60.00   82
 49  \w     37.00 103.00   0.50    0.45    --   76.70-125.00   0.00  132
 50  \w     38.00 102.00   0.50    0.45    --   76.70-125.00-120.00  128
 51  \w     50.00  87.00   0.50    0.45    --   77.25-107.00-177.85   74
 52  \w     45.00 103.00   0.50    0.45    --   76.70-125.00-180.00  116
 53  \w     56.00 102.00   0.50    0.45    --   76.70-125.00-150.00   92
 54  \w     42.00  70.00   0.50    0.45    --   77.25 -94.00 -74.68   56
 55  \w     75.00 102.00   0.50    0.45    --   76.70 135.00  -5.00   54
 56  \w     81.00 112.00   0.50    0.45    --   77.25  91.00-139.41   62
 57  \w     69.00 104.00   0.50    0.45    --   76.70 135.00 174.00   70
;
_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      0.0645739000
_diffrn_orient_matrix_UB_12      -0.1205624000
_diffrn_orient_matrix_UB_13      0.0272638000
_diffrn_orient_matrix_UB_21      0.0794505000
_diffrn_orient_matrix_UB_22      0.0958799000
_diffrn_orient_matrix_UB_23      0.0360684000
_diffrn_orient_matrix_UB_31      -0.0616188000
_diffrn_orient_matrix_UB_32      -0.0027464000
_diffrn_orient_matrix_UB_33      0.0639344000
_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  0.0377
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            54571
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.952
_diffrn_reflns_theta_min         2.245
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.156
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.452
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
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    1.245
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.171(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         10219
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0817P)^2^+0.3194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1018
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                9952
_reflns_number_total             10219
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00580a2.cif
_cod_data_source_block           rea914_mp_abs_
_cod_depositor_comments
'Adding full bibliography for 1568634--1568643.cif.'
_cod_database_code               1568642
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C13H19PS
_shelx_estimated_absorpt_t_max   0.858
_shelx_estimated_absorpt_t_min   0.413
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.829(15)
 0.171(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C41(H41A,H41B), C47(H47A,H47B), C14(H14A,H14B), C16(H16A,H16B), C42(H42A,
 H42B), C27(H27A,H27B), C7(H7A,H7B), C20(H20A,H20B), C15(H15A,H15B), C1(H1A,
 H1B), C45(H45A,H45B), C6(H6A,H6B), C31(H31A,H31B), C34(H34A,H34B), C17(H17A,
 H17B), C33(H33A,H33B), C29(H29A,H29B), C19(H19A,H19B), C5(H5A,H5B), C32(H32A,
 H32B), C30(H30A,H30B), C43(H43A,H43B), C46(H46A,H46B), C44(H44A,H44B), C4(H4A,
 H4B), C18(H18A,H18B), C2(H2A,H2B), C3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 C26(H26), C49(H49), C25(H25), C22(H22), C36(H36), C13(H13), C50(H50), C9(H9),
 C24(H24), C53(H53), C23(H23), C40(H40), C10(H10), C51(H51), C12(H12), C38(H38),
  C52(H52), C11(H11), C37(H37), C39(H39)
;
_shelx_res_checksum              56379
_shelx_hkl_checksum              39956
_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 1.598
_oxdiff_exptl_absorpt_empirical_full_min 0.739