Acid‒ammonium heterodimer and N~(ammonium)~‒H···N~(pyridine)~ synthon preference in three salts of nicotinic acid with (1<i>R</i>,2<i>R</i>)-1,2-diphenylethylenediamine
Han, Yang; Fu, Qiang; Zhang, Peng; Guan, Hongyu; Guo, Fang; Acta Crystallographica Section B 75 (2019) –; doi:10.1107/S2052520619000477

data_2108385
_publ_section_title
;
 Acid--ammonium heterodimer and
 N~(ammonium)~--H&#x00B7;&#x00B7;&#x00B7;N~(pyridine)~ synthon preference
 in three salts of nicotinic acid with
 (1<i>R</i>,2<i>R</i>)-1,2-diphenylethylenediamine
;
_journal_coeditor_code           AW5017SUP1
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520619000477
_journal_volume                  75
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C6 H4 N O2), 2(C7 H9 N)'
_chemical_formula_sum            'C26 H26 N4 O4'
_chemical_formula_weight         458.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 129.963(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.479(6)
_cell_length_b                   8.602(2)
_cell_length_c                   16.899(4)
_cell_measurement_reflns_used    4568
_cell_measurement_temperature    273
_cell_measurement_theta_max      28.000
_cell_measurement_theta_min      3.413
_cell_volume                     2615.9(11)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11704
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         28.358
_diffrn_reflns_theta_min         3.414
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_description       plate
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1504 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         6271
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0596
_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^)+(0.0962P)^2^+0.3861P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.1742
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.913
_reflns_number_gt                4303
_reflns_number_total             6271
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            aw5017sup1.cif
_cod_data_source_block           DPEN1-NA2
_cod_original_cell_volume        2616.1(11)
_cod_database_code               2108385
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C16A)
\\sim Ueq, Uanis(C15A) \\sim Ueq, Uanis(C17A) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C19B) = Uanis(C19)
Uanis(C18) = Uanis(C18A)
Uanis(C16A) = Uanis(C16)
3. Others
 Sof(C19B)=Sof(H19B)=Sof(N4A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=
 Sof(C18A)=Sof(C15A)=Sof(H15A)=1-FVAR(1)
 Sof(N4)=Sof(C18)=Sof(C17)=Sof(H17)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=
 Sof(C19)=Sof(H19)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C1(H1), C8(H8)
4.b Aromatic/amide H refined with riding coordinates:
 C25(H25), C23(H23), C19B(H19B), C21(H21), C22(H22), C10(H10), C7(H7), C5(H5),
 C14(H14), C13(H13), C12(H12), C3(H3), C11(H11), C4(H4), C6(H6), C17(H17),
 C15(H15), C16(H16), C16A(H16A), C17A(H17A), C15A(H15A), C19(H19)
;
_shelx_res_checksum              48587
_shelx_hkl_checksum              16276
_olex2_submission_special_instructions 'No special instructions were received'
_cod_database_fobs_code 2108385