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_2108386
_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), C4 H8 O2'
_chemical_formula_sum            'C30 H34 N4 O6'
_chemical_formula_weight         546.61
_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
_audit_creation_date             2018-11-06
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 118.613(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.9673(11)
_cell_length_b                   8.8676(4)
_cell_length_c                   16.7749(8)
_cell_measurement_reflns_used    9833
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.275
_cell_measurement_theta_min      3.091
_cell_volume                     2999.2(3)
_computing_cell_refinement       '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)'
_diffrn_ambient_temperature      273.0
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25955
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         28.333
_diffrn_reflns_theta_min         3.090
_exptl_absorpt_coefficient_mu    0.085
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_description       needle
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 2721 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.27(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         7385
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0516
_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^)+(0.0861P)^2^+0.8946P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1426
_refine_ls_wR_factor_ref         0.1518
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                6427
_reflns_number_total             7385
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            aw5017sup1.cif
_cod_data_source_block           DPEN1-NA2-EA1
_cod_original_cell_volume        2999.2(2)
_cod_database_code               2108386
_cod_database_fobs_code          2108386
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.981
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C5(H5), C19(H19), C15(H15), C12(H12), C17(H17), C1(H1), C23(H23),
 C4(H4), C21(H21), C8(H8), C11(H11), C16(H16), C22(H22), C3(H3), C10(H10),
 C2(H2), C9(H9)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              4507
_shelx_hkl_checksum              27368
_olex2_submission_special_instructions 'No special instructions were received'