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_4036801
_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         'C19 H14 N O2, Cl'
_chemical_formula_sum            'C19 H14 Cl N O2'
_chemical_formula_weight         323.76
_chemical_name_systematic
;
 3-(3-hydroxy-1-oxo-1H-inden-2-yl)-1-methylquinolin-1-ium chloride
;
_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   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 102.474(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2551(4)
_cell_length_b                   6.3701(2)
_cell_length_c                   22.6746(8)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      72.1
_cell_measurement_theta_min      4.0
_cell_volume                     1446.28(9)
_computing_cell_refinement       SAINT
_computing_data_collection       APEX2
_computing_data_reduction        SAINT
_computing_molecular_graphics    Shelxtl
_computing_publication_material  publCIF
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SHELXD
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture with Photon100 detector'
_diffrn_measurement_method       'rotation in \f and \w, 1\%, shutterless'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            19704
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.141
_diffrn_reflns_theta_min         3.993
_diffrn_source                   'I\mS microfocus'
_exptl_absorpt_coefficient_mu    2.417
_exptl_absorpt_correction_T_max  0.9582
_exptl_absorpt_correction_T_min  0.7508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2015)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       plates
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2814
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0489
_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^)+(0.0850P)^2^+1.7500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1449
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2600
_reflns_number_total             2814
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00561_si_001.cif
_cod_data_source_block           schm84
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4036801
_shelx_estimated_absorpt_t_min   0.477
_shelx_estimated_absorpt_t_max   0.953
_shelxl_version_number           2014-3
_shelx_res_checksum              83517
_shelx_hkl_checksum              61500