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_2017814
_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          'C16 H18 N4 O2'
_chemical_formula_moiety         'C16 H18 N4 O2'
_chemical_formula_sum            'C16 H18 N4 O2'
_chemical_formula_weight         298.34
_chemical_name_systematic
;
<i>N</i>,<i>N</i>'-(butane-1,4-diyl)bis(pyridine-2-carboxamide)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                83.509(4)
_cell_angle_beta                 77.256(4)
_cell_angle_gamma                81.005(4)
_cell_formula_units_Z            1
_cell_length_a                   5.3215(2)
_cell_length_b                   7.2734(4)
_cell_length_c                   9.7993(5)
_cell_measurement_reflns_used    2485
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      32.0597
_cell_measurement_theta_min      2.8391
_cell_volume                     364.18(3)
_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 0.880
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur 2 CCD'
_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  0.0149
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3732
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.11
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58394
_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    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             158
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.275
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         2246
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0850P)^2^+0.0083P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1360
_reflns_number_gt                1810
_reflns_number_total             2246
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fg3197.cif
_cod_data_source_block           II
_cod_database_code               2017814
_cod_database_fobs_code          2017814