Amide hydrogen bonding: control of the molecular and extended structures of two symmetrical pyridine-2-carboxamide derivatives
Munro, Orde Q.; Wilson, Colin; Acta Crystallographica Section C 66 (2010) o535–o539; doi:10.1107/S0108270110039983

data_2017813
_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
;
<i>N</i>,<i>N</i>'-(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 <i>et al.</i>, 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       \w
_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/[\s^2^(Fo^2^)+(0.0661P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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>2\s(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