Concise Synthesis of Phospholene and Its P-Stereogenic Derivatives.
Hu, Wei; Li, Er-Qing; Duan, Zheng; Mathey, François; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00545

data_4038399
_publ_section_title
;
 Concise Synthesis of Phospholene and Its P-Stereogenic Derivatives.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00545
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H19 O2 P, 0.5(H2 O)'
_chemical_formula_sum            'C22 H20 O2.5 P'
_chemical_formula_weight         355.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-01-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.734(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.6268(12)
_cell_length_b                   8.2898(9)
_cell_length_c                   11.4377(6)
_cell_measurement_reflns_used    1233
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.8310
_cell_measurement_theta_min      3.9430
_cell_volume                     1914.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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   -104.00 -11.00   1.00    1.25    --  -33.50 -37.00  90.00   93
  2  \w   -102.00 -15.00   1.00    1.25    --  -33.50 -57.00-150.00   87
  3  \w     14.00 107.00   1.00    1.25    --   36.47  37.00 -90.00   93
  4  \w    -33.00  65.00   1.00    1.25    --   36.47 -77.00 -60.00   98
  5  \w    -32.00  55.00   1.00    1.25    --   36.47 -57.00 -60.00   87
  6  \w     46.00  99.00   1.00    4.00    --  108.00 -94.00   0.00   53
  7  \w     87.00 178.00   1.00    4.00    --  108.00  30.00 -60.00   91
  8  \w     94.00 120.00   1.00    4.00    --  108.00  61.00 120.00   26
  9  \w     40.00  81.00   1.00    4.00    --  108.00 -94.00  60.00   41
 10  \w    141.00 176.00   1.00    4.00    --  108.00  61.00 120.00   35
 11  \w    102.00 128.00   1.00    4.00    --  108.00 -45.00 120.00   26
 12  \w     89.00 166.00   1.00    4.00    --  108.00  45.00-120.00   77
 13  \w     44.00  96.00   1.00    4.00    --  108.00 -45.00 120.00   52
 14  \w     88.00 118.00   1.00    4.00    --  108.00 -45.00 -90.00   30
 15  \w     38.00  68.00   1.00    4.00    --  108.00 -45.00 -90.00   30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0224212000
_diffrn_orient_matrix_UB_12      0.0657698000
_diffrn_orient_matrix_UB_13      0.1277945000
_diffrn_orient_matrix_UB_21      0.0726368000
_diffrn_orient_matrix_UB_22      -0.0345235000
_diffrn_orient_matrix_UB_23      -0.0058419000
_diffrn_orient_matrix_UB_31      0.0059524000
_diffrn_orient_matrix_UB_32      0.1704578000
_diffrn_orient_matrix_UB_33      -0.0505812000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3674
_diffrn_reflns_point_group_measured_fraction_full 0.735
_diffrn_reflns_point_group_measured_fraction_max 0.735
_diffrn_reflns_theta_full        67.064
_diffrn_reflns_theta_max         67.064
_diffrn_reflns_theta_min         3.947
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.385
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.233
_exptl_crystal_description       block
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 582 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2526
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0721P)^2^+0.2586P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1291
_reflns_Friedel_coverage         0.373
_reflns_Friedel_fraction_full    0.432
_reflns_Friedel_fraction_max     0.432
_reflns_number_gt                2287
_reflns_number_total             2526
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00545_si_002.cif
_cod_data_source_block           201912346
_cod_depositor_comments
;

2025-09-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C44 H40 O5 P2'
_cod_original_formula_weight         710.70
_cod_original_formula_moiety         '2(C22 H19 O2 P), H2 O'
_cod_original_formula_units_Z            2
_cod_database_code               4038399
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C40H40O2N1P1
_shelx_estimated_absorpt_t_max   0.874
_shelx_estimated_absorpt_t_min   0.799
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 O3(H3A)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10),
 C15(H15), C17(H17), C18(H18), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              80991
_shelx_hkl_checksum              55373
_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 1.288
_oxdiff_exptl_absorpt_empirical_full_min 0.824