Positively and negatively charged NHN hydrogen bonds in one molecule: synergistic strengthening effect, superbasicity and acetonitrile capture
Vlasenko, Marina P.; Ozeryanskii, Valery A.; Pozharskii, Alexander F.; Khoroshilova, Olesya V.; New Journal of Chemistry 43 (2019) 7557–; doi:10.1039/C9NJ00965E

data_7058323
_publ_section_title
;
 Positively and negatively charged NHN hydrogen bonds in one molecule:
 synergistic strengthening effect, superbasicity and acetonitrile capture
;
_journal_issue                   20
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7557
_journal_paper_doi               10.1039/C9NJ00965E
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C28 H32 N4 O4 S2, C2 H3 N'
_chemical_formula_sum            'C30 H35 N5 O4 S2'
_chemical_formula_weight         593.75
_chemical_melting_point          492.6(5)
_chemical_name_common
'4,5-Bis(dimethylamino)-1,8-bis(p-toluenesulfonamido)naphthalene, zwitterion'
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2019-02-21 deposited with the CCDC.    2019-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.406(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6465(18)
_cell_length_b                   16.788(3)
_cell_length_c                   18.275(4)
_cell_measurement_reflns_used    9902
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.83
_cell_measurement_theta_min      2.23
_cell_volume                     2958.7(10)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0347
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            68326
_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         28.873
_diffrn_reflns_theta_min         1.647
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       prizm
_exptl_crystal_F_000             1256
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         7756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0540P)^2^+1.8166P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6586
_reflns_number_total             7756
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj00965e2.cif
_cod_data_source_block           s51
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '219-220 deg.C' was changed to
'492.6(5)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7058322--7058323.cif.
;
_cod_original_cell_volume        2958.8(10)
_cod_database_code               7058323
_shelxl_version_number           2014/6
_shelx_res_checksum              39256