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_4036800
_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 H13 D3 N O2, F6 P'
_chemical_formula_sum            'C20 H13 D3 F6 N O2 P'
_chemical_formula_weight         450.33
_chemical_name_systematic
;
 3-((2-((methoxy-d3)carbonyl)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                 106.370(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8271(8)
_cell_length_b                   8.2406(5)
_cell_length_c                   17.2704(9)
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.5
_cell_volume                     1888.08(19)
_computing_cell_refinement       APEX3
_computing_data_collection       APEX3
_computing_data_reduction        SAINT
_computing_molecular_graphics    Shelxtl
_computing_publication_material  publCIF
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE with Photon100 detector'
_diffrn_measurement_method       'rotation in \f and \w, 1\%, shutterless'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            29589
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.524
_diffrn_reflns_theta_min         2.221
_diffrn_source                   'INCOATEC microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.9866
_exptl_absorpt_correction_T_min  0.9238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_description       plates
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0044(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0339P)^2^+1.2976P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0878
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3479
_reflns_number_total             4338
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00561_si_001.cif
_cod_data_source_block           schm94
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4036800
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.925
_shelx_estimated_absorpt_t_max   0.983
_shelx_res_checksum              86718
_shelx_hkl_checksum              94369