Electrophilic phosphonium cations catalyze hydroarylation and hydrothiolation of olefins
Pérez, Manuel; Mahdi, Tayseer; Hounjet, Lindsay J.; Stephan, Douglas W.; Chemical Communications (Cambridge, United Kingdom) 51 (2015) 11301–11304; doi:10.1039/c5cc03572d

data_7117430
_publ_section_title
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 Electrophilic phosphonium cations catalyze hydroarylation and
 hydrothiolation of olefins
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   56
_journal_name_full
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 Chemical Communications (Cambridge, United Kingdom)
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_journal_page_first              11301
_journal_page_last               11304
_journal_paper_doi               10.1039/c5cc03572d
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C20 H18 O'
_chemical_formula_sum            'C20 H18 O'
_chemical_formula_weight         274.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             2015-02-01
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-02-01 deposited with the CCDC.
2015-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                64.69(2)
_cell_angle_beta                 79.19(2)
_cell_angle_gamma                85.90(3)
_cell_formula_units_Z            6
_cell_length_a                   9.390(6)
_cell_length_b                   15.536(11)
_cell_length_c                   17.758(11)
_cell_measurement_reflns_used    4167
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.85
_cell_measurement_theta_min      2.36
_cell_volume                     2300(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      149.71
_diffrn_measured_fraction_theta_full 0.9781
_diffrn_measured_fraction_theta_max 0.9781
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1840
_diffrn_reflns_av_unetI/netI     0.3234
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            37768
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1005 before and 0.0663 after correction.
The Ratio of minimum to maximum transmission is 0.8990.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.1867
_exptl_crystal_description       cubic
_exptl_crystal_F_000             874.3809
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.1602
_refine_diff_density_min         -0.6808
_refine_diff_density_rms         0.1517
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             13.7825
_refine_ls_goodness_of_fit_ref   0.9108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    94
_refine_ls_number_parameters     567
_refine_ls_number_reflns         7919
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9108
_refine_ls_R_factor_all          0.2263
_refine_ls_R_factor_gt           0.0958
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1970P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2355
_refine_ls_wR_factor_ref         0.3466
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -10
_reflns_limit_k_max              18
_reflns_limit_k_min              -16
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                2841
_reflns_number_total             7919
_reflns_threshold_expression     I>=2u(I)
_cod_duplicate_entry             7117402
_cod_data_source_file            c5cc03572d2.cif
_cod_data_source_block           MP005a_0m
_cod_depositor_comments
;

2017-03-09
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C20 H18 O), C20 H17 O'
_cod_original_formula_sum        'C60 H53 O3'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     822.09
_cod_database_code               7117430
_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. Others
 Fixed Uiso: H(0.05) H3(0.05) H2(0.05) H1(0.05)
 Fixed X: H(0.80644) H3(0.70401) H2(0.46759) H1(-0.25849)
 Fixed Y: H(0.52818) H3(0.57334) H2(0.62593) H1(0.41874)
 Fixed Z: H(0.46572) H3(0.40479) H2(0.38397) H1(0.53263)
3.a Me refined with riding coordinates:
 C62(H62a,H62b,H62c), C42(H42a,H42b,H42c), C20(H20a,H20b,H20c)
3.b Aromatic/amide H refined with riding coordinates:
 C44(H44), C45(H45), C47(H47), C48(H48), C51(H51), C52(H52), C53(H53),
 C54(H54), C55(H55), C57(H57), C58(H58), C59(H59), C60(H60), C61(H61), C24(H24),
  C25(H25), C27(H27), C28(H28), C31(H31), C32(H32), C33(H33), C34(H34),
 C35(H35), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41), C2(H2a), C5(H5),
 C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19)
;
_olex2_submission_special_instructions 'No special instructions were received'