Cationic 5-phosphonio-substituted N-heterocyclic carbenes.
Schwedtmann, Kai; Schoemaker, Robin; Hennersdorf, Felix; Bauzá, Antonio; Frontera, Antonio; Weiss, Robert; Weigand, Jan J.; Dalton transactions (Cambridge, England : 2003) 45 (2016) 11384–11396; doi:10.1039/c6dt01871h

data_7039673
_publ_section_title
;
 Cationic 5-phosphonio-substituted N-heterocyclic carbenes.
;
_journal_issue                   28
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11384
_journal_page_last               11396
_journal_paper_doi               10.1039/c6dt01871h
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C39 H44 Cl2 N2 P, C F3 O3 S, C6 H4 F2'
_chemical_formula_sum            'C46 H48 Cl2 F5 N2 O3 P S'
_chemical_formula_weight         905.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-06-02 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.813(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.2304(11)
_cell_length_b                   18.8946(12)
_cell_length_c                   29.2339(18)
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      2.50
_cell_volume                     8933.5(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            188008
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.807
_diffrn_reflns_theta_min         1.285
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/3 (Bruker,2014) was used for absorption correction. wR2(int) was 0.0756 before and 0.0601 after correction. The Ratio of minimum to maximum transmission is 0.9136. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             3776
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1164
_refine_ls_number_reflns         19058
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0689
_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^)+41.1324P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1567
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15029
_reflns_number_total             19058
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6dt01871h2.cif
_cod_data_source_block           10OTf
_cod_depositor_comments
'Adding full bibliography for 7039669--7039682.cif.'
_cod_database_code               7039673
_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. Restrained distances
 F1B-C79B \\sim F2B-C79B \\sim F3B-C79B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F45) = Uanis(F2B)
Uanis(C79A) = Uanis(C79B)
Uanis(O4A) = Uanis(O4B)
Uanis(O5A) = Uanis(O5B)
Uanis(F39) = Uanis(O6B)
Uanis(F34) = Uanis(F4B)
Uanis(F6B) = Uanis(O6A)
Uanis(C80B) = Uanis(C80A)
Uanis(F27A) = Uanis(F1B)
Uanis(O3A) = Uanis(F3B)
4. Others
 Sof(O4B)=Sof(F1B)=Sof(S2B)=Sof(F6B)=Sof(F5B)=Sof(C80B)=Sof(O5B)=Sof(F4B)=
 Sof(O6B)=Sof(S1B)=Sof(O3B)=Sof(F2B)=Sof(C79B)=Sof(F3B)=1-FVAR(1)
 Sof(S1A)=Sof(S2A)=Sof(F32)=Sof(F34)=Sof(F39)=Sof(F44)=Sof(F45)=Sof(O6A)=
 Sof(O5A)=Sof(O3A)=Sof(C79A)=Sof(C80A)=Sof(O4A)=Sof(F27A)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C64(H64), C25(H25), C61(H61), C52(H52), C13(H13), C22(H22), C10(H10), C49(H49)
5.b Aromatic/amide H refined with riding coordinates:
 C75(H75), C89(H89), C83(H83), C90(H90), C74(H74), C84(H84), C69(H69),
 C86(H86), C36(H36), C71(H71), C37(H37), C85(H85), C91(H91), C18(H18), C32(H32),
  C38(H38), C30(H30), C92(H92), C70(H70), C20(H20), C68(H68), C35(H35),
 C29(H29), C39(H39), C19(H19), C33(H33), C57(H57), C72(H72), C59(H59), C58(H58),
  C76(H76), C78(H78), C31(H31), C7(H7), C6(H6), C47(H47), C46(H46), C77(H77),
 C8(H8), C45(H45)
5.c Idealised Me refined as rotating group:
 C51(H51A,H51B,H51C), C14(H14A,H14B,H14C), C65(H65A,H65B,H65C), C26(H26A,H26B,
 H26C), C53(H53A,H53B,H53C), C12(H12A,H12B,H12C), C66(H66A,H66B,H66C), C23(H23A,
 H23B,H23C), C27(H27A,H27B,H27C), C11(H11A,H11B,H11C), C24(H24A,H24B,H24C),
 C63(H63A,H63B,H63C), C62(H62A,H62B,H62C), C54(H54A,H54B,H54C), C50(H50A,H50B,
 H50C), C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'