#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/78/2017813.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2017813
loop_
_publ_author_name
'Munro, Orde Q.'
'Wilson, Colin'
_publ_section_title
;
 Amide hydrogen bonding: control of the molecular and extended structures
 of two symmetrical pyridine-2-carboxamide derivatives
;
_journal_coeditor_code           FG3197
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o535
_journal_page_last               o539
_journal_paper_doi               10.1107/S0108270110039983
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H16 N4 O2'
_chemical_formula_moiety         'C15 H16 N4 O2'
_chemical_formula_sum            'C15 H16 N4 O2'
_chemical_formula_weight         284.32
_chemical_name_systematic
;
N,N'-(propane-1,3-diyl)bis(pyridine-2-carboxamide)
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.140(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.7558(15)
_cell_length_b                   9.9188(7)
_cell_length_c                   9.7665(6)
_cell_measurement_reflns_used    3923
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.9627
_cell_measurement_theta_min      2.7650
_cell_volume                     1523.9(2)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_molecular_graphics
'Mercury (CSD 2.0 Version; Macrae et al., 2008)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.4190
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device_type  'Oxford Xcalibur 2 CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7542
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.01
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.9465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[CrysAlis RED (Oxford Diffraction, 2008); empirical absorption
correction
using spherical harmonics, implemented in the SCALE3 ABSPACK scaling algorithm]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.112
_refine_diff_density_min         -0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2452
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0661P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1014
_reflns_number_gt                1882
_reflns_number_total             2452
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg3197.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2017813
_cod_database_fobs_code          2017813
loop_
_symmetry_equiv_pos_as_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'
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 -0.17348(17) 0.7986(3) -0.0231(3) 0.0741(6) Uani d . 1 . .
H H1 -0.1954 0.7927 0.0521 0.089 Uiso calc R 1 . .
C C2 -0.17990(18) 0.9194(3) -0.0950(3) 0.0804(7) Uani d . 1 . .
H H2A -0.2047 0.9938 -0.0677 0.097 Uiso calc R 1 . .
C C3 -0.14934(19) 0.9282(3) -0.2066(3) 0.0776(7) Uani d . 1 . .
H H3A -0.1528 1.0091 -0.2565 0.093 Uiso calc R 1 . .
C C4 -0.11290(13) 0.8155(2) -0.2457(2) 0.0622(5) Uani d . 1 . .
H H4 -0.0924 0.8186 -0.3229 0.075 Uiso calc R 1 . .
C C5 -0.10814(10) 0.69896(18) -0.16657(16) 0.0462(3) Uani d . 1 . .
C C6 -0.06680(9) 0.57519(18) -0.20077(15) 0.0421(3) Uani d . 1 . .
C C7 -0.01312(14) 0.34915(19) -0.1169(2) 0.0574(4) Uani d . 1 . .
H H7A -0.0361 0.3169 -0.2166 0.069 Uiso calc R 1 . .
H H7B -0.0260 0.2824 -0.0550 0.069 Uiso calc R 1 . .
C C8 0.08334(13) 0.3623(2) -0.0731(2) 0.0608(5) Uani d . 1 . .
H H8A 0.1072 0.2732 -0.0730 0.073 Uiso calc R 1 . .
H H8B 0.0960 0.4156 -0.1463 0.073 Uiso calc R 1 . .
C C9 0.12664(12) 0.4264(2) 0.0747(2) 0.0560(4) Uani d . 1 . .
H H9A 0.1858 0.4425 0.0872 0.067 Uiso calc R 1 . .
H H9B 0.1004 0.5131 0.0771 0.067 Uiso calc R 1 . .
C C10 0.18819(10) 0.27292(16) 0.28139(17) 0.0452(3) Uani d . 1 . .
C C11 0.17313(10) 0.20021(17) 0.40577(17) 0.0460(3) Uani d . 1 . .
C C12 0.23058(12) 0.1048(2) 0.4837(2) 0.0583(4) Uani d . 1 . .
H H12 0.2791 0.0858 0.4614 0.070 Uiso calc R 1 . .
C C13 0.21475(15) 0.0381(3) 0.5956(3) 0.0734(6) Uani d . 1 . .
H H13 0.2519 -0.0278 0.6494 0.088 Uiso calc R 1 . .
C C14 0.14317(18) 0.0709(3) 0.6257(3) 0.0880(8) Uani d . 1 . .
H H14 0.1310 0.0276 0.7006 0.106 Uiso calc R 1 . .
C C15 0.08952(19) 0.1686(4) 0.5439(3) 0.0966(10) Uani d . 1 . .
H H15 0.0417 0.1911 0.5667 0.116 Uiso calc R 1 . .
N N1 -0.13726(10) 0.68912(17) -0.05605(16) 0.0566(4) Uani d . 1 . .
N N2 -0.05466(9) 0.47532(15) -0.10567(15) 0.0466(3) Uani d . 1 . .
N N3 0.12243(10) 0.34503(16) 0.19586(16) 0.0522(3) Uani d . 1 . .
N N4 0.10263(12) 0.2327(2) 0.4338(2) 0.0716(5) Uani d . 1 . .
O O1 -0.04648(8) 0.57020(14) -0.31106(12) 0.0532(3) Uani d . 1 . .
O O2 0.25671(8) 0.26360(15) 0.26290(16) 0.0624(3) Uani d . 1 . .
H H2 -0.0697(15) 0.490(2) -0.025(3) 0.060(6) Uiso d . 1 . .
H H3 0.0807(17) 0.350(2) 0.226(3) 0.059(6) Uiso d . 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 123.2(2) ?
N1 C1 H1 . . 118.4 ?
C2 C1 H1 . . 118.4 ?
C3 C2 C1 . . 118.8(2) ?
C3 C2 H2A . . 120.6 ?
C1 C2 H2A . . 120.6 ?
C2 C3 C4 . . 119.5(2) ?
C2 C3 H3A . . 120.3 ?
C4 C3 H3A . . 120.3 ?
C5 C4 C3 . . 117.83(18) ?
C5 C4 H4 . . 121.1 ?
C3 C4 H4 . . 121.1 ?
N1 C5 C4 . . 123.34(16) ?
N1 C5 C6 . . 116.47(15) ?
C4 C5 C6 . . 120.18(14) ?
O1 C6 N2 . . 123.95(16) ?
O1 C6 C5 . . 120.82(15) ?
N2 C6 C5 . . 115.24(12) ?
N2 C7 C8 . . 113.13(16) ?
N2 C7 H7A . . 109.0 ?
C8 C7 H7A . . 109.0 ?
N2 C7 H7B . . 109.0 ?
C8 C7 H7B . . 109.0 ?
H7A C7 H7B . . 107.8 ?
C9 C8 C7 . . 114.58(15) ?
C9 C8 H8A . . 108.6 ?
C7 C8 H8A . . 108.6 ?
C9 C8 H8B . . 108.6 ?
C7 C8 H8B . . 108.6 ?
H8A C8 H8B . . 107.6 ?
N3 C9 C8 . . 113.67(17) ?
N3 C9 H9A . . 108.8 ?
C8 C9 H9A . . 108.8 ?
N3 C9 H9B . . 108.8 ?
C8 C9 H9B . . 108.8 ?
H9A C9 H9B . . 107.7 ?
O2 C10 N3 . . 124.08(16) ?
O2 C10 C11 . . 120.53(15) ?
N3 C10 C11 . . 115.39(14) ?
N4 C11 C12 . . 123.37(17) ?
N4 C11 C10 . . 116.94(14) ?
C12 C11 C10 . . 119.69(16) ?
C11 C12 C13 . . 118.64(19) ?
C11 C12 H12 . . 120.7 ?
C13 C12 H12 . . 120.7 ?
C14 C13 C12 . . 118.53(19) ?
C14 C13 H13 . . 120.7 ?
C12 C13 H13 . . 120.7 ?
C13 C14 C15 . . 119.3(2) ?
C13 C14 H14 . . 120.4 ?
C15 C14 H14 . . 120.4 ?
N4 C15 C14 . . 123.3(2) ?
N4 C15 H15 . . 118.3 ?
C14 C15 H15 . . 118.3 ?
C5 N1 C1 . . 117.31(18) ?
C6 N2 C7 . . 123.53(14) ?
C6 N2 H2 . . 117.7(15) ?
C7 N2 H2 . . 118.6(15) ?
C10 N3 C9 . . 123.00(15) ?
C10 N3 H3 . . 114.2(16) ?
C9 N3 H3 . . 122.1(16) ?
C15 N4 C11 . . 116.87(19) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.336(3) ?
C1 C2 . 1.374(4) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.357(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.389(3) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.377(3) ?
C4 H4 . 0.9300 ?
C5 N1 . 1.3325(19) ?
C5 C6 . 1.503(2) ?
C6 O1 . 1.2374(17) ?
C6 N2 . 1.325(2) ?
C7 N2 . 1.454(2) ?
C7 C8 . 1.528(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.514(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 N3 . 1.454(2) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 O2 . 1.226(2) ?
C10 N3 . 1.338(2) ?
C10 C11 . 1.507(2) ?
C11 N4 . 1.340(2) ?
C11 C12 . 1.377(2) ?
C12 C13 . 1.379(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.369(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.375(4) ?
C14 H14 . 0.9300 ?
C15 N4 . 1.332(3) ?
C15 H15 . 0.9300 ?
N2 H2 . 0.92(3) ?
N3 H3 . 0.85(3) ?
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 H2 O1 2_565 0.92(3) 2.08(3) 2.8688(18) 144(2)
N3 H3 O1 2_565 0.85(3) 2.18(3) 2.931(2) 147(2)
C1 H1 O2 3_455 0.93 2.47 3.397(3) 175
C13 H13 O2 2_555 0.93 2.58 3.366(3) 143
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . 1.1(5) ?
C1 C2 C3 C4 . . . . 0.3(4) ?
C2 C3 C4 C5 . . . . -1.1(4) ?
C3 C4 C5 N1 . . . . 0.6(3) ?
C3 C4 C5 C6 . . . . -178.0(2) ?
N1 C5 C6 O1 . . . . 171.93(16) ?
C4 C5 C6 O1 . . . . -9.4(2) ?
N1 C5 C6 N2 . . . . -8.0(2) ?
C4 C5 C6 N2 . . . . 170.74(17) ?
N2 C7 C8 C9 . . . . 52.3(2) ?
C7 C8 C9 N3 . . . . 66.7(2) ?
O2 C10 C11 N4 . . . . 169.13(19) ?
N3 C10 C11 N4 . . . . -11.2(2) ?
O2 C10 C11 C12 . . . . -11.2(2) ?
N3 C10 C11 C12 . . . . 168.40(16) ?
N4 C11 C12 C13 . . . . 0.6(3) ?
C10 C11 C12 C13 . . . . -178.99(18) ?
C11 C12 C13 C14 . . . . -0.9(3) ?
C12 C13 C14 C15 . . . . 0.1(4) ?
C13 C14 C15 N4 . . . . 1.1(6) ?
C4 C5 N1 C1 . . . . 0.7(3) ?
C6 C5 N1 C1 . . . . 179.36(18) ?
C2 C1 N1 C5 . . . . -1.6(4) ?
O1 C6 N2 C7 . . . . 2.2(3) ?
C5 C6 N2 C7 . . . . -177.88(15) ?
C8 C7 N2 C6 . . . . 75.5(2) ?
O2 C10 N3 C9 . . . . -3.2(3) ?
C11 C10 N3 C9 . . . . 177.22(15) ?
C8 C9 N3 C10 . . . . 103.1(2) ?
C14 C15 N4 C11 . . . . -1.4(5) ?
C12 C11 N4 C15 . . . . 0.5(4) ?
C10 C11 N4 C15 . . . . -179.8(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 562074
