Dipolar Bent and Linear Acetylenes Substituted by Cationic Quinolinium and Anionic Benzoates. Formation of Mesomeric Betaines.
Schmidt, Andreas; Batsyts, Sviatoslav; Smeyanov, Alexey; Freese, Tyll; Hübner, Eike G; Nieger, Martin; The Journal of organic chemistry 81 (2016) 4202–4209; doi:10.1021/acs.joc.6b00561

data_4036799
_publ_section_title
;
 Dipolar Bent and Linear Acetylenes Substituted by Cationic Quinolinium
 and Anionic Benzoates. Formation of Mesomeric Betaines.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4202
_journal_page_last               4209
_journal_paper_doi               10.1021/acs.joc.6b00561
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C20 H16 N O2, F6 P'
_chemical_formula_sum            'C20 H16 F6 N O2 P'
_chemical_formula_weight         447.31
_chemical_name_systematic
;
3-((2-(methoxycarbonyl)phenyl)ethynyl)-1-methylquinolin-1-ium 
hexafluorophosphate(V)
;
_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'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.117(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8445(5)
_cell_length_b                   8.2667(3)
_cell_length_c                   17.2086(6)
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      72.10
_cell_measurement_theta_min      3.64
_cell_volume                     1892.09(12)
_computing_cell_refinement       'APEX3 v2015.9-RC2 (Bruker AXS)'
_computing_data_collection       'APEX3 v2015.9-RC2 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    Shelxtl
_computing_publication_material  publCIF
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 VENTURE with Photon100 detector'
_diffrn_measurement_method       'rotation in \f and \w, 0.5\%, shutterless'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28286
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.136
_diffrn_reflns_theta_min         3.641
_diffrn_source                   'INCOATEC microfocus sealed tube'
_exptl_absorpt_coefficient_mu    1.999
_exptl_absorpt_correction_T_max  0.9424
_exptl_absorpt_correction_T_min  0.8063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_description       plates
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0454P)^2^+0.8220P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0887
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3370
_reflns_number_total             3717
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00561_si_001.cif
_cod_data_source_block           schm87
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4036799
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.691
_shelx_estimated_absorpt_t_max   0.942
_shelx_res_checksum              124
_shelx_hkl_checksum              49790