Copper-catalyzed arylation of polycyclic aromatic hydrocarbons by the P[double bond, length as m-dash]O group.
Niu, Yuan; Qi, Zhichao; Lou, Qinxin; Bai, Pengbo; Yang, Shangdong; Chemical communications (Cambridge, England) 56 (2020) 14721–14724; doi:10.1039/d0cc06639g

data_7127718
_publ_section_title
;
 Copper-catalyzed arylation of polycyclic aromatic hydrocarbons by the
 P[double bond, length as m-dash]O group.
;
_journal_issue                   93
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14721
_journal_page_last               14724
_journal_paper_doi               10.1039/d0cc06639g
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C24 H28 Cl O P'
_chemical_formula_sum            'C24 H28 Cl O P'
_chemical_formula_weight         398.88
_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     direct
_audit_creation_date             2020-04-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-07-08 deposited with the CCDC.	2020-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.370(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7689(4)
_cell_length_b                   15.1355(6)
_cell_length_c                   13.0960(5)
_cell_measurement_reflns_used    2982
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.8750
_cell_measurement_theta_min      9.1500
_cell_volume                     2172.38(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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     42.00  69.00   1.00    1.00    --    0.00  57.00  90.00   27
  2  \w      6.00  36.00   1.00    1.00    --    0.00  57.00  90.00   30
  3  \w     -3.00  26.00   1.00    2.00    --   54.00 -38.00  60.00   29
  4  \w     43.00  74.00   1.00    2.00    --   54.00 -38.00  60.00   31
  5  \w     94.00 134.00   1.00    3.00    --  108.00 -38.00   0.00   40
  6  \w     80.00 141.00   1.00    3.00    --  108.00 -25.00  90.00   61
  7  \w     86.00 158.00   1.00    3.00    --  108.00  38.00  90.00   72
  8  \w    107.00 135.00   1.00    3.00    --  108.00 111.00  30.00   28
  9  \w    100.00 177.00   1.00    3.00    --  108.00 111.00  90.00   77
 10  \w     69.00 114.00   1.00    2.00    --   54.00  57.00 -60.00   45
 11  \w     39.00 123.00   1.00    2.00    --   54.00  57.00-150.00   84
 12  \w     39.00 142.00   1.00    3.00    --  108.00 -91.00   0.00  103
 13  \w     79.00 113.00   1.00    3.00    --  108.00-111.00 -60.00   34
 14  \w     51.00  86.00   1.00    2.00    --   54.00-125.00-120.00   35
 15  \w     46.00 111.00   1.00    3.00    --  108.00-111.00-180.00   65
 16  \w    -14.00  54.00   1.00    2.00    --   54.00 -57.00-120.00   68
 17  \w    -45.00   1.00   1.00    1.00    --    0.00 -57.00 -90.00   46
 18  \w     39.00  65.00   1.00    3.00    --  108.00 -25.00  90.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1173685000
_diffrn_orient_matrix_UB_12      0.0513155000
_diffrn_orient_matrix_UB_13      0.0125321000
_diffrn_orient_matrix_UB_21      -0.0759276000
_diffrn_orient_matrix_UB_22      0.0842616000
_diffrn_orient_matrix_UB_23      -0.0429256000
_diffrn_orient_matrix_UB_31      0.0147394000
_diffrn_orient_matrix_UB_32      0.0251833000
_diffrn_orient_matrix_UB_33      0.1181045000
_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  0.0289
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7989
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         4.034
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.320
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3830
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0477
_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^)+(0.0525P)^2^+0.7091P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1267
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2953
_reflns_number_total             3830
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc06639g2.cif
_cod_data_source_block           niuyuan_0419
_cod_original_cell_volume        2172.39(15)
_cod_database_code               7127718
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C9(H9), C10(H10), C11(H11), C13(H13), C15(H15), C17(H17), C18(H18),
 C20(H20), C23(H23)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              17920
_shelx_hkl_checksum              83726
_olex2_date_sample_data_collection 2020-04-20
_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 1.864
_oxdiff_exptl_absorpt_empirical_full_min 0.622