Oxaphosphacyclophanes Constructed from a Bis(triphenylphosphine oxide) Moiety Linked by Dioxyalkyl Chains: Synthesis and Crystal Structures.
Katagiri, Kosuke; Ohara, Masahiro; Ikehara, Masahiro; Higashimura, Ikkei; Isono, Koshiro; ACS omega 5 (2020) 23621–23630; doi:10.1021/acsomega.0c02177

data_4518027
_publ_section_title
;
 Oxaphosphacyclophanes Constructed from a Bis(triphenylphosphine oxide)
 Moiety Linked by Dioxyalkyl Chains: Synthesis and Crystal Structures.
;
_journal_issue                   37
_journal_name_full               'ACS omega'
_journal_page_first              23621
_journal_page_last               23630
_journal_paper_doi               10.1021/acsomega.0c02177
_journal_volume                  5
_journal_year                    2020
_chemical_formula_moiety         '0.5(C42 H38 O6 P2), C H Cl3'
_chemical_formula_sum            'C22 H20 Cl3 O3 P'
_chemical_formula_weight         469.70
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-05-10
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                76.4018(17)
_cell_angle_beta                 81.4278(17)
_cell_angle_gamma                80.7315(19)
_cell_formula_units_Z            8
_cell_length_a                   11.0373(3)
_cell_length_b                   20.9634(4)
_cell_length_c                   24.3544(5)
_cell_measurement_reflns_used    12631
_cell_measurement_temperature    173
_cell_measurement_theta_max      76.6910
_cell_measurement_theta_min      3.7550
_cell_volume                     5369.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.963
_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    -40.00   4.00   0.50    1.50    --    0.00 -19.00 -90.00   88
  2  \w    -57.00 -10.00   0.50    1.50    --    0.00 -37.00   0.00   94
  3  \w    -16.00  10.00   0.50    1.50    --    0.00  37.00-120.00   52
  4  \w    -66.00  22.00   0.50    1.50    --    0.00 -57.00-120.00  176
  5  \w    -21.00  85.00   0.50    1.50    --    0.00  57.00-120.00  212
  6  \w    -17.00  52.00   0.50    1.50    --    0.00  37.00 120.00  138
  7  \w     94.00 119.00   0.50    1.50    --  101.00 -82.00 120.00   50
  8  \w     12.00 116.00   0.50    1.50    --  101.00 -30.00 -30.00  208
  9  \w     25.00 127.00   0.50    1.50    --  101.00 -82.00-150.00  204
 10  \w     48.00 132.00   0.50    1.50    --  101.00 -82.00  60.00  168
 11  \w     18.00 105.00   0.50    1.50    --  101.00 -61.00-150.00  174
 12  \w     32.00 122.00   0.50    1.50    --  101.00 -61.00  60.00  180
 13  \w     13.00 114.00   0.50    1.50    --  101.00 -30.00-120.00  202
 14  \w     23.00  76.00   0.50    1.50    --  101.00 -82.00   0.00  106
 15  \w     91.00 183.00   0.50    1.50    --  101.00  15.00 -30.00  184
 16  \w     12.00 131.00   0.50    1.50    --  101.00 -82.00 -90.00  238
 17  \w     86.00 111.00   0.50    1.50    --  101.00 -82.00   0.00   50
 18  \w    151.00 177.00   0.50    1.50    --  101.00  30.00-150.00   52
 19  \w     18.00 124.00   0.50    1.50    --  101.00 -15.00  60.00  212
 20  \w     92.00 180.00   0.50    1.50    --  101.00  15.00  60.00  176
 21  \w     61.00 108.00   0.50    1.50    --  101.00 -82.00 150.00   94
 22  \w     77.00 102.00   0.50    1.50    --  101.00 -82.00-120.00   50
 23  \w     93.00 119.00   0.50    1.50    --  101.00 -82.00 -38.96   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0295845000
_diffrn_orient_matrix_UB_12      0.0480055000
_diffrn_orient_matrix_UB_13      -0.0562157000
_diffrn_orient_matrix_UB_21      -0.1267484000
_diffrn_orient_matrix_UB_22      0.0246009000
_diffrn_orient_matrix_UB_23      0.0292441000
_diffrn_orient_matrix_UB_31      0.0577523000
_diffrn_orient_matrix_UB_32      0.0539155000
_diffrn_orient_matrix_UB_33      0.0166563000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            64652
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.374
_diffrn_reflns_theta_min         3.760
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.800
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_description       prism
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1153
_refine_ls_number_reflns         21950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0657
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1230P)^2^+0.8356P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2273
_refine_ls_wR_factor_ref         0.2632
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9123
_reflns_number_total             21950
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c02177_si_001.cif
_cod_data_source_block           exp_375
_cod_depositor_comments
'Adding full bibliography for 4518025--4518030.cif.'
_cod_database_code               4518027
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C42H38O6P2
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: Cl2(0.7) Cl5(0.7) Cl2A(0.7) Cl7(0.7) Cl6(0.7) Cl11(0.7) Cl8(0.7)
 Cl4(0.7) Cl10(0.7) Cl3(0.7) Cl9(0.7) H85(0.7) H85A(0.3) H86(0.7) H86A(0.3)
 H88(0.7) H88A(0.3) H87(0.7) H87A(0.3) Cl12(0.7) Cl19(0.3) Cl14(0.3) Cl18(0.3)
 Cl24(0.3) Cl21(0.3) Cl13(0.3) Cl23(0.3) Cl17(0.3) Cl15(0.3) Cl20(0.3)
 Cl22(0.3) Cl16(0.3)
3.a Ternary CH refined with riding coordinates:
 C85(H85), C85(H85A), C86(H86), C86(H86A), C88(H88), C88(H88A), C87(H87),
 C87(H87A)
3.b Secondary CH2 refined with riding coordinates:
 C82(H82A,H82B), C37(H37A,H37B), C79(H79A,H79B), C41(H41A,H41B), C83(H83A,
 H83B), C81(H81A,H81B), C84(H84A,H84B), C39(H39A,H39B), C40(H40A,H40B),
 C80(H80A,H80B), C38(H38A,H38B), C42(H42A,H42B)
3.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C74(H74), C33(H33), C57(H57), C15(H15), C75(H75), C35(H35),
 C36(H36), C59(H59), C60(H60), C78(H78), C44(H44), C17(H17), C2(H2), C18(H18),
 C77(H77), C62(H62), C32(H32), C20(H20), C56(H56), C8(H8), C51(H51), C68(H68),
 C26(H26), C50(H50), C12(H12), C69(H69), C72(H72), C9(H9), C27(H27), C30(H30),
 C11(H11), C29(H29), C71(H71), C54(H54), C66(H66), C6(H6), C53(H53), C45(H45),
 C48(H48), C63(H63), C3(H3), C24(H24), C21(H21), C46(H46), C5(H5), C4(H4),
 C64(H64), C47(H47), C65(H65), C22(H22), C23(H23)
;
_olex2_exptl_crystal_mounting_method loop
_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 2.356
_oxdiff_exptl_absorpt_empirical_full_min 0.642