Zwitterion formation and subsequent carboxylate–pyridinium NH synthon generation through isomerization of 2-anilinonicotinic acid
Yue, Pengyun; Dong, Caiqiao; Zhang, Mingtao; Xu, Danrui; Parkin, Sean; Li, Tonglei; Li, Conggang; Yu, Faquan; Long, Sihui; CrystEngComm 20 (2018) 6126–; doi:10.1039/C8CE01255E

data_7231522
_publ_section_title
;
 Zwitterion formation and subsequent carboxylate--pyridinium NH synthon
 generation through isomerization of 2-anilinonicotinic acid
;
_journal_issue                   40
_journal_name_full               CrystEngComm
_journal_page_first              6126
_journal_paper_doi               10.1039/C8CE01255E
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C12 H10 N2 O2'
_chemical_formula_sum            'C12 H10 N2 O2'
_chemical_formula_weight         214.22
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2018-08-28 deposited with the CCDC.
2018-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.685(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8415(2)
_cell_length_b                   13.7771(4)
_cell_length_c                   6.9369(2)
_cell_measurement_reflns_used    4588
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1010.84(5)
_computing_cell_refinement       '<i>SCALEPACK</i> (Otwinowski & Minor, 2006)'
_computing_data_collection       '<i>COLLECT</i> (Nonius, 1998)'
_computing_data_reduction        '<i>DENZO-SMN</i> (Otwinowski & Minor, 2006)'
_computing_molecular_graphics    '<i>XP in SHELXTL</i> (Sheldrick, 2008)'
_computing_publication_material
'<i>SHELX</i> (Sheldrick, 2008) and <i>CIFFIX</i> (Parkin, 2013)'
_computing_structure_refinement  '<i>SHELXL-2018/1</i> (Sheldrick, 2015b)'
_computing_structure_solution    '<i>SHELXT</i> (Sheldrick, 2015a)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 9.1
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       '\f and \w scans at fixed \c = 55\%'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8954
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_min         1.925
_diffrn_source                   'fine-focus sealed-tube'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '<i>Scalepack</i> (Otwinowski & Minor, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2310
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0488
_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^)+(0.0841P)^2^+0.0085P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1421
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1596
_reflns_number_total             2310
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce01255e2.cif
_cod_data_source_block           k07235
_cod_depositor_comments
'Adding full bibliography for 7231522--7231525.cif.'
_cod_database_code               7231522
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.990
_exptl_absorpt_special_details
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the x-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;
_shelx_res_checksum              31888