#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:32:27 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180477 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/46/7214683.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_7214683
loop_
_publ_author_name
'Évora, António O. L.'
'Castro, Ricardo A. E.'
'Maria, Teresa M. R.'
'Rosado, Mário T. S.'
'Silva, M. Ramos'
'Canotilho, João'
'Eusébio, M. Ermelinda S.'
_publ_section_title
;
 Resolved structures of two picolinamide polymorphs. Investigation of the
 dimorphic system behaviour under conditions relevant to co-crystal
 synthesis
;
_journal_issue                   24
_journal_name_full               CrystEngComm
_journal_page_first              8649
_journal_paper_doi               10.1039/c2ce26244d
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C6 H6 N2 O'
_chemical_formula_sum            'C6 H6 N2 O'
_chemical_formula_weight         122.13
_chemical_name_systematic
;
α - picolinamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.728(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1578(4)
_cell_length_b                   7.0249(5)
_cell_length_c                   16.2192(11)
_cell_measurement_reflns_used    1039
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.68
_cell_measurement_theta_min      2.56
_cell_volume                     577.40(7)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'APEX2 (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3319
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.74
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0384
_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)+(0.0461P)²+0.1319P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0985
_reflns_number_gt                848
_reflns_number_total             1083
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c2ce26244d.txt
_cod_data_source_block           picolow2
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7214683
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
O1 O 0.1999(2) -0.18310(17) -0.04244(8) 0.0368(4) Uani 1 1 d
N1 N -0.2883(3) -0.4612(2) -0.16831(8) 0.0296(4) Uani 1 1 d
N2 N -0.2430(3) -0.1461(2) -0.06844(9) 0.0290(4) Uani 1 1 d
H2A H -0.232(3) -0.036(3) -0.0386(11) 0.035 Uiso 1 1 d
H2B H -0.404(4) -0.202(3) -0.0870(11) 0.035 Uiso 1 1 d
C1 C -0.0570(3) -0.4301(2) -0.11668(9) 0.0244(4) Uani 1 1 d
C2 C 0.1465(3) -0.5605(2) -0.10318(10) 0.0289(4) Uani 1 1 d
H2 H 0.309(4) -0.527(3) -0.0639(11) 0.035 Uiso 1 1 d
C3 C 0.1098(4) -0.7337(3) -0.14425(11) 0.0348(5) Uani 1 1 d
H3 H 0.239(4) -0.824(3) -0.1373(12) 0.042 Uiso 1 1 d
C4 C -0.1241(4) -0.7665(3) -0.19860(11) 0.0354(5) Uani 1 1 d
H4 H -0.157(4) -0.888(3) -0.2289(12) 0.042 Uiso 1 1 d
C5 C -0.3153(4) -0.6276(3) -0.20883(11) 0.0341(4) Uani 1 1 d
H5 H -0.485(4) -0.646(3) -0.2456(12) 0.041 Uiso 1 1 d
C6 C -0.0244(3) -0.2411(2) -0.07281(10) 0.0261(4) Uani 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0239(6) 0.0371(7) 0.0501(8) -0.0154(6) 0.0086(5) -0.0062(5)
N1 0.0280(8) 0.0327(8) 0.0284(7) -0.0042(6) 0.0060(6) -0.0042(6)
N2 0.0251(7) 0.0264(8) 0.0355(8) -0.0061(6) 0.0054(6) -0.0020(6)
C1 0.0260(8) 0.0268(9) 0.0220(8) 0.0014(7) 0.0083(6) -0.0035(7)
C2 0.0298(9) 0.0314(9) 0.0268(9) 0.0019(7) 0.0085(7) -0.0006(7)
C3 0.0435(11) 0.0281(10) 0.0367(10) 0.0029(8) 0.0173(9) 0.0038(8)
C4 0.0461(11) 0.0313(10) 0.0325(10) -0.0088(8) 0.0172(9) -0.0100(8)
C5 0.0343(10) 0.0377(10) 0.0310(10) -0.0087(8) 0.0079(8) -0.0088(8)
C6 0.0260(9) 0.0275(9) 0.0254(9) -0.0009(7) 0.0067(7) -0.0037(7)
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
C5 N1 C1 116.66(15)
C6 N2 H2A 119.1(11)
C6 N2 H2B 119.8(11)
H2A N2 H2B 120.2(16)
N1 C1 C2 123.54(15)
N1 C1 C6 116.62(14)
C2 C1 C6 119.84(14)
C1 C2 C3 118.42(16)
C1 C2 H2 118.6(11)
C3 C2 H2 123.0(11)
C4 C3 C2 118.78(17)
C4 C3 H3 119.8(12)
C2 C3 H3 121.4(12)
C3 C4 C5 118.84(17)
C3 C4 H4 121.0(11)
C5 C4 H4 120.1(11)
N1 C5 C4 123.71(17)
N1 C5 H5 114.8(11)
C4 C5 H5 121.5(11)
O1 C6 N2 123.70(15)
O1 C6 C1 119.55(14)
N2 C6 C1 116.75(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C6 1.2390(18)
N1 C5 1.335(2)
N1 C1 1.342(2)
N2 C6 1.323(2)
N2 H2A 0.91(2)
N2 H2B 0.917(19)
C1 C2 1.380(2)
C1 C6 1.501(2)
C2 C3 1.383(2)
C2 H2 0.983(18)
C3 C4 1.375(3)
C3 H3 0.91(2)
C4 C5 1.375(3)
C4 H4 0.98(2)
C5 H5 0.971(18)
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
C5 N1 C1 C2 -1.1(2)
C5 N1 C1 C6 178.54(14)
N1 C1 C2 C3 -0.7(2)
C6 C1 C2 C3 179.70(13)
C1 C2 C3 C4 1.9(2)
C2 C3 C4 C5 -1.4(3)
C1 N1 C5 C4 1.7(2)
C3 C4 C5 N1 -0.5(3)
N1 C1 C6 O1 -161.32(15)
C2 C1 C6 O1 18.3(2)
N1 C1 C6 N2 19.3(2)
C2 C1 C6 N2 -161.12(14)
