#------------------------------------------------------------------------------
#$Date: 2016-08-27 04:50:40 +0300 (Sat, 27 Aug 2016) $
#$Revision: 186046 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/39/1543980.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_1543980
loop_
_publ_author_name
'Dziuk, Błażej'
'Ośmiałowski, Borys'
'Ejsmont, Krzysztof'
'Zarychta, Bartosz'
_publ_section_title
;
 N,N'-Bis(pyridin-2-yl)octanediamide
;
_journal_coeditor_code           HB4070
_journal_issue                   8
_journal_name_full               IUCrData
_journal_page_first              x161309
_journal_paper_doi               10.1107/S2414314616013092
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C18 H22 N4 O2'
_chemical_formula_moiety         'C18 H22 N4 O2'
_chemical_formula_sum            'C18 H22 N4 O2'
_chemical_formula_weight         326.39
_chemical_name_systematic
;
N,N'-Bis(pyridin-2-yl)octanediamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 111.497(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9289(7)
_cell_length_b                   13.2908(6)
_cell_length_c                   11.5000(6)
_cell_measurement_reflns_used    5224
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      25.242
_cell_measurement_theta_min      3.450
_cell_volume                     1696.43(17)
_computing_cell_refinement
;
CrysAlisRED (Oxford Diffraction, 2008)
;
_computing_data_collection
;
CrysAlisCCD (Oxford Diffraction, 2008)
;
_computing_data_reduction
;
CrysAlisRED (Oxford Diffraction, 2008)
;
_computing_molecular_graphics
;
SHELXL2013 (Sheldrick, 2015)
;
_computing_publication_material
;
SHELXL2013 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2013 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean '1024 x 1024 with blocks 2 x 2'
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5224
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         3.450
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       irregular
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.152
_refine_ls_extinction_coef       0.0012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2013 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.946
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0315
_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)+(0.0429P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0729
_reflns_number_gt                1125
_reflns_number_total             1494
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb4070sup1.cif
_cod_data_source_block           I
_cod_database_code               1543980
_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.
;
_shelxl_version_number           .2013
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
O O1 0.15817(8) 0.27316(7) 0.84143(8) 0.0259(3) Uani d 1
N N1 0.10057(9) 0.57410(8) 0.92312(10) 0.0228(3) Uani d 1
N N2 0.08189(9) 0.40263(7) 0.92055(10) 0.0189(3) Uani d 1
H H2A 0.0393 0.4149 0.9652 0.023 Uiso calc 1
C C1 0.12421(10) 0.48726(9) 0.87675(11) 0.0177(3) Uani d 1
C C2 0.18323(11) 0.48219(10) 0.79260(12) 0.0213(3) Uani d 1
H H2 0.1975 0.4206 0.7621 0.026 Uiso calc 1
C C3 0.21992(11) 0.57095(10) 0.75567(13) 0.0238(3) Uani d 1
H H3 0.2594 0.5699 0.6994 0.029 Uiso calc 1
C C4 0.19788(11) 0.66159(10) 0.80261(12) 0.0235(3) Uani d 1
H H4 0.2225 0.7223 0.7795 0.028 Uiso calc 1
C C5 0.13834(11) 0.65855(9) 0.88437(13) 0.0253(3) Uani d 1
H H5 0.1229 0.7195 0.9154 0.030 Uiso calc 1
C C6 0.09926(11) 0.30281(9) 0.90189(11) 0.0184(3) Uani d 1
C C7 0.03884(11) 0.23330(9) 0.96366(11) 0.0196(3) Uani d 1
H H7A -0.0464 0.2492 0.9333 0.023 Uiso calc 1
H H7B 0.0713 0.2462 1.0529 0.023 Uiso calc 1
C C8 0.05278(11) 0.12258(9) 0.94244(12) 0.0203(3) Uani d 1
H H8A 0.1378 0.1071 0.9668 0.024 Uiso calc 1
H H8B 0.0141 0.1080 0.8540 0.024 Uiso calc 1
C C9 -0.00115(12) 0.05536(9) 1.01516(12) 0.0196(3) Uani d 1
H H9A 0.0430 0.0652 1.1038 0.023 Uiso calc 1
H H9B -0.0839 0.0756 0.9973 0.023 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle
C1 N1 C5 . 116.16(11)
C6 N2 C1 . 128.73(11)
C6 N2 H2A . 115.6
C1 N2 H2A . 115.6
N1 C1 C2 . 123.42(11)
N1 C1 N2 . 113.04(11)
C2 C1 N2 . 123.53(12)
C3 C2 C1 . 118.14(12)
C3 C2 H2 . 120.9
C1 C2 H2 . 120.9
C2 C3 C4 . 119.85(13)
C2 C3 H3 . 120.1
C4 C3 H3 . 120.1
C5 C4 C3 . 117.52(12)
C5 C4 H4 . 121.2
C3 C4 H4 . 121.2
N1 C5 C4 . 124.92(12)
N1 C5 H5 . 117.5
C4 C5 H5 . 117.5
O1 C6 N2 . 123.56(12)
O1 C6 C7 . 123.17(11)
N2 C6 C7 . 113.27(10)
C6 C7 C8 . 115.01(10)
C6 C7 H7A . 108.5
C8 C7 H7A . 108.5
C6 C7 H7B . 108.5
C8 C7 H7B . 108.5
H7A C7 H7B . 107.5
C7 C8 C9 . 112.96(10)
C7 C8 H8A . 109.0
C9 C8 H8A . 109.0
C7 C8 H8B . 109.0
C9 C8 H8B . 109.0
H8A C8 H8B . 107.8
C9 C9 C8 5_557 113.43(13)
C9 C9 H9A 5_557 108.9
C8 C9 H9A . 108.9
C9 C9 H9B 5_557 108.9
C8 C9 H9B . 108.9
H9A C9 H9B . 107.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C6 . 1.2209(14)
N1 C1 . 1.3440(16)
N1 C5 . 1.3448(16)
N2 C6 . 1.3717(16)
N2 C1 . 1.4000(16)
N2 H2A . 0.8600
C1 C2 . 1.3914(18)
C2 C3 . 1.3783(17)
C2 H2 . 0.9300
C3 C4 . 1.3840(18)
C3 H3 . 0.9300
C4 C5 . 1.3711(19)
C4 H4 . 0.9300
C5 H5 . 0.9300
C6 C7 . 1.5010(17)
C7 C8 . 1.5108(17)
C7 H7A . 0.9700
C7 H7B . 0.9700
C8 C9 . 1.5185(18)
C8 H8A . 0.9700
C8 H8B . 0.9700
C9 C9 5_557 1.515(2)
C9 H9A . 0.9700
C9 H9B . 0.9700
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2A N1 5_567 0.86 2.45 3.3065(15) 171
C2 H2 O1 . 0.93 2.28 2.8716(15) 121
C4 H4 O1 4_556 0.93 2.42 3.1585(15) 136

_cod_database_fobs_code 1543980
