#------------------------------------------------------------------------------
#$Date: 2019-03-21 05:32:57 +0200 (Thu, 21 Mar 2019) $
#$Revision: 214247 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/83/2108388.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2108388
loop_
_publ_author_name
'Han, Yang'
'Fu, Qiang'
'Zhang, Peng'
'Guan, Hongyu'
'Guo, Fang'
_publ_section_title
;
 Acid--ammonium heterodimer and
 N(ammonium)--H···N(pyridine) synthon preference
 in three salts of nicotinic acid with
 (1R,2R)-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         'C14 H18 N2, 2(C6 H4 N O2)'
_chemical_formula_sum            'C26 H26 N4 O4'
_chemical_formula_weight         458.51
_space_group_crystal_system      hexagonal
_space_group_IT_number           179
_space_group_name_Hall           'P 65 2 (0 0 1)'
_space_group_name_H-M_alt        'P 65 2 2'
_symmetry_space_group_name_Hall  'P 65 2 (0 0 1)'
_symmetry_space_group_name_H-M   'P 65 2 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   13.854(3)
_cell_length_b                   13.854(3)
_cell_length_c                   27.167(8)
_cell_measurement_reflns_used    2017
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      2
_cell_volume                     4515.7(19)
_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    'SIR2004 (Burla et al.,  2007)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            34749
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.025
_diffrn_reflns_theta_min         6.122
_exptl_absorpt_coefficient_mu    0.566
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.012
_exptl_crystal_description       block
_exptl_crystal_F_000             1452
_refine_diff_density_max         0.095
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
;
 Flack x determined using 605 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.45(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2862
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0421
_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/[σ²(Fo²)+(0.0573P)²+0.2696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1133
_reflns_Friedel_coverage         0.637
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1940
_reflns_number_total             2862
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            aw5017sup1.cif
_cod_data_source_block           DPEN1-INA2
_cod_original_cell_volume        4516(2)
_cod_database_code               2108388
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C7(H7), C8(H8), C9(H9), C10(H10), C2(H2), C1(H1), C5(H5), C4(H4)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+5/6'
'-y, x-y, z+2/3'
'-x, -y, z+1/2'
'-x+y, -x, z+1/3'
'y, -x+y, z+1/6'
'-y, -x, -z+1/6'
'x-y, -y, -z'
'x, x-y, -z+5/6'
'y, x, -z+2/3'
'-x+y, y, -z+1/2'
'-x, -x+y, -z+1/3'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
N2 N 0.45838(18) 0.1044(2) 0.52518(7) 0.0460(5) Uani 1 1 d .
C13 C 0.3352(2) 0.0398(2) 0.52234(7) 0.0441(6) Uani 1 1 d .
H13 H 0.3082 -0.0063 0.5521 0.053 Uiso 1 1 calc R
C11 C 0.2865(2) 0.1146(2) 0.52192(8) 0.0503(7) Uani 1 1 d .
C12 C 0.3315(3) 0.2090(2) 0.49233(8) 0.0593(8) Uani 1 1 d .
H12 H 0.3909 0.2245 0.4716 0.071 Uiso 1 1 calc R
C7 C 0.2894(3) 0.2788(3) 0.49357(10) 0.0777(11) Uani 1 1 d .
H7 H 0.3220 0.3433 0.4746 0.093 Uiso 1 1 calc R
C8 C 0.2002(4) 0.2549(4) 0.52221(13) 0.0948(12) Uani 1 1 d .
H8 H 0.1710 0.3025 0.5225 0.114 Uiso 1 1 calc R
C9 C 0.1531(4) 0.1611(4) 0.55075(16) 0.1033(13) Uani 1 1 d .
H9 H 0.0908 0.1440 0.5698 0.124 Uiso 1 1 calc R
C10 C 0.1977(3) 0.0922(3) 0.55126(11) 0.0747(9) Uani 1 1 d .
H10 H 0.1674 0.0300 0.5717 0.090 Uiso 1 1 calc R
O1 O 0.5498(2) 0.3887(2) 0.39974(7) 0.0906(8) Uani 1 1 d .
O2 O 0.5103(2) 0.5136(3) 0.42527(8) 0.1048(10) Uani 1 1 d .
N1 N 0.7383(2) 0.5002(2) 0.56347(8) 0.0651(7) Uani 1 1 d .
C6 C 0.5553(3) 0.4562(3) 0.42988(9) 0.0614(8) Uani 1 1 d .
C3 C 0.6193(2) 0.4708(2) 0.47701(8) 0.0539(7) Uani 1 1 d .
C2 C 0.6211(3) 0.5390(3) 0.51406(10) 0.0738(10) Uani 1 1 d .
H2 H 0.5821 0.5772 0.5108 0.089 Uiso 1 1 calc R
C1 C 0.6816(3) 0.5503(3) 0.55635(10) 0.0765(10) Uani 1 1 d .
H1 H 0.6817 0.5966 0.5811 0.092 Uiso 1 1 calc R
C5 C 0.7351(3) 0.4335(3) 0.52789(10) 0.0710(9) Uani 1 1 d .
H5 H 0.7743 0.3959 0.5324 0.085 Uiso 1 1 calc R
C4 C 0.6770(3) 0.4163(3) 0.48445(9) 0.0650(8) Uani 1 1 d .
H4 H 0.6773 0.3683 0.4606 0.078 Uiso 1 1 calc R
H2A H 0.478(2) 0.169(3) 0.5465(10) 0.066(8) Uiso 1 1 d .
H2B H 0.488(2) 0.060(2) 0.5450(11) 0.074(9) Uiso 1 1 d .
H2C H 0.494(3) 0.123(3) 0.4931(12) 0.084(10) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C13 N2 H2A 106.6(17) . .
C13 N2 H2B 110.1(16) . .
C13 N2 H2C 113.0(19) . .
H2A N2 H2B 103(2) . .
H2A N2 H2C 114(2) . .
H2B N2 H2C 109(2) . .
N2 C13 C13 111.41(14) . 8_556
N2 C13 H13 107.5 . .
N2 C13 C11 111.4(2) . .
C13 C13 H13 107.5 8_556 .
C11 C13 C13 111.45(15) . 8_556
C11 C13 H13 107.5 . .
C12 C11 C13 120.8(2) . .
C10 C11 C13 120.4(3) . .
C10 C11 C12 118.8(3) . .
C11 C12 H12 119.8 . .
C7 C12 C11 120.4(3) . .
C7 C12 H12 119.8 . .
C12 C7 H7 119.8 . .
C8 C7 C12 120.4(3) . .
C8 C7 H7 119.8 . .
C7 C8 H8 119.9 . .
C7 C8 C9 120.1(4) . .
C9 C8 H8 119.9 . .
C8 C9 H9 120.0 . .
C8 C9 C10 120.0(4) . .
C10 C9 H9 120.0 . .
C11 C10 C9 120.2(3) . .
C11 C10 H10 119.9 . .
C9 C10 H10 119.9 . .
C1 N1 C5 116.6(2) . .
O1 C6 O2 124.6(3) . .
O1 C6 C3 118.6(3) . .
O2 C6 C3 116.7(3) . .
C2 C3 C6 121.3(3) . .
C4 C3 C6 121.3(3) . .
C4 C3 C2 117.4(2) . .
C3 C2 H2 120.4 . .
C3 C2 C1 119.1(3) . .
C1 C2 H2 120.4 . .
N1 C1 C2 124.0(3) . .
N1 C1 H1 118.0 . .
C2 C1 H1 118.0 . .
N1 C5 H5 118.0 . .
N1 C5 C4 123.9(3) . .
C4 C5 H5 118.0 . .
C3 C4 C5 119.0(3) . .
C3 C4 H4 120.5 . .
C5 C4 H4 120.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N2 C13 1.481(3) .
N2 H2A 0.99(3) .
N2 H2B 1.05(3) .
N2 H2C 0.97(3) .
C13 C13 1.544(4) 8_556
C13 H13 0.9800 .
C13 C11 1.494(4) .
C11 C12 1.389(4) .
C11 C10 1.364(4) .
C12 H12 0.9300 .
C12 C7 1.356(4) .
C7 H7 0.9300 .
C7 C8 1.354(5) .
C8 H8 0.9300 .
C8 C9 1.367(6) .
C9 H9 0.9300 .
C9 C10 1.373(5) .
C10 H10 0.9300 .
O1 C6 1.217(3) .
O2 C6 1.236(3) .
N1 C1 1.295(4) .
N1 C5 1.323(4) .
C6 C3 1.512(3) .
C3 C2 1.373(4) .
C3 C4 1.362(4) .
C2 H2 0.9300 .
C2 C1 1.385(4) .
C1 H1 0.9300 .
C5 H5 0.9300 .
C5 C4 1.380(4) .
C4 H4 0.9300 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
N2 C13 C11 C12 45.0(3) .
N2 C13 C11 C10 -134.0(2) .
C13 C13 C11 C12 -80.1(3) 8_556
C13 C13 C11 C10 101.0(3) 8_556
C13 C11 C12 C7 -177.5(2) .
C13 C11 C10 C9 -179.9(3) .
C11 C12 C7 C8 -2.6(5) .
C12 C11 C10 C9 1.1(5) .
C12 C7 C8 C9 1.1(5) .
C7 C8 C9 C10 1.5(6) .
C8 C9 C10 C11 -2.5(6) .
C10 C11 C12 C7 1.5(4) .
O1 C6 C3 C2 -174.8(3) .
O1 C6 C3 C4 4.9(4) .
O2 C6 C3 C2 4.1(5) .
O2 C6 C3 C4 -176.2(3) .
N1 C5 C4 C3 0.2(5) .
C6 C3 C2 C1 -179.5(3) .
C6 C3 C4 C5 179.3(3) .
C3 C2 C1 N1 0.3(6) .
C2 C3 C4 C5 -1.0(4) .
C1 N1 C5 C4 0.9(5) .
C5 N1 C1 C2 -1.1(5) .
C4 C3 C2 C1 0.8(5) .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.025 0.898 0.095 1390 255 ' '

_cod_database_fobs_code 2108388
