#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/43/7214363.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_7214363
loop_
_publ_author_name
'Chan, H. C. Stephen'
'Woollam, Grahame R.'
'Wagner, Trixie'
'Schmidt, Martin U.'
'Lewis, Richard A.'
_publ_section_title
;
 Can picolinamide be a promising cocrystal former?
;
_journal_issue                   21
_journal_name_full               CrystEngComm
_journal_page_first              4365
_journal_paper_doi               10.1039/c4ce00265b
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C6 H6 N2 O'
_chemical_formula_weight         122.13
_chemical_name_common            'pico form I'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 96.704(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   5.2870(10)
_cell_length_b                   11.163(2)
_cell_length_c                   19.899(4)
_cell_measurement_reflns_used    5038
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      4.47
_cell_volume                     1166.4(4)
_computing_cell_refinement       'Saint V7.36A (Bruker AXS, 2006)'
_computing_data_collection       'SMART V5.632 (Bruker AXS, 2003)'
_computing_data_reduction        'Saint V7.36A (Bruker AXS, 2006)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'three-circle goniometer'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_source         microsource
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11388
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_min         4.47
_exptl_absorpt_coefficient_mu    0.818
_exptl_absorpt_correction_T_max  0.9374
_exptl_absorpt_correction_T_min  0.8871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2055
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0462P)²+0.5543P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1031
_reflns_number_gt                1783
_reflns_number_total             2055
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00265b2.cif
_cod_data_source_block           STC27a
_cod_depositor_comments
'Adding full bibliography for 7214357--7214365.cif.'
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7214363
#BEGIN Tags that were not found in dictionaries:
_chemical_source_common          EE/isohex
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_refinement_flags
N1 N 0.5841(3) 0.13245(12) 0.25999(7) 0.0263(3) Uani 1 1 d .
C2 C 0.5699(3) 0.20089(14) 0.31520(8) 0.0257(4) Uani 1 1 d .
H2 H 0.7044 0.1969 0.3512 0.031 Uiso 1 1 calc R
C3 C 0.3665(3) 0.27690(14) 0.32148(8) 0.0265(4) Uani 1 1 d .
H3 H 0.3618 0.3239 0.3611 0.032 Uiso 1 1 calc R
C4 C 0.1705(3) 0.28316(15) 0.26903(8) 0.0270(4) Uani 1 1 d .
H4 H 0.0296 0.3348 0.2723 0.032 Uiso 1 1 calc R
C5 C 0.1813(3) 0.21356(14) 0.21173(8) 0.0237(3) Uani 1 1 d .
H5 H 0.0484 0.2166 0.1752 0.028 Uiso 1 1 calc R
C6 C 0.3901(3) 0.13955(13) 0.20887(7) 0.0202(3) Uani 1 1 d .
C7 C 0.4076(3) 0.06266(13) 0.14764(7) 0.0209(3) Uani 1 1 d .
O8 O 0.2302(2) 0.05656(10) 0.10147(5) 0.0253(3) Uani 1 1 d .
N9 N 0.6228(2) 0.00228(11) 0.14786(6) 0.0218(3) Uani 1 1 d .
H9A H 0.6454 -0.0454 0.1139 0.026 Uiso 1 1 calc R
H9B H 0.7434 0.0098 0.1820 0.026 Uiso 1 1 calc R
N11 N 0.3167(2) -0.31272(12) -0.09306(7) 0.0255(3) Uani 1 1 d .
C12 C 0.3446(3) -0.40354(15) -0.13535(8) 0.0292(4) Uani 1 1 d .
H12 H 0.2122 -0.4179 -0.1710 0.035 Uiso 1 1 calc R
C13 C 0.5557(3) -0.47787(15) -0.13016(8) 0.0283(4) Uani 1 1 d .
H13 H 0.5666 -0.5419 -0.1612 0.034 Uiso 1 1 calc R
C14 C 0.7493(3) -0.45679(15) -0.07901(9) 0.0304(4) Uani 1 1 d .
H14 H 0.8969 -0.5060 -0.0742 0.036 Uiso 1 1 calc R
C15 C 0.7258(3) -0.36254(15) -0.03465(8) 0.0283(4) Uani 1 1 d .
H15 H 0.8571 -0.3455 0.0008 0.034 Uiso 1 1 calc R
C16 C 0.5058(3) -0.29387(13) -0.04344(7) 0.0215(3) Uani 1 1 d .
C17 C 0.4764(3) -0.19162(14) 0.00432(8) 0.0237(3) Uani 1 1 d .
O18 O 0.6483(2) -0.17193(11) 0.05105(5) 0.0325(3) Uani 1 1 d .
N19 N 0.2624(3) -0.12900(12) -0.00600(7) 0.0258(3) Uani 1 1 d .
H19A H 0.2356 -0.0693 0.0212 0.031 Uiso 1 1 calc R
H19B H 0.1472 -0.1471 -0.0400 0.031 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 N1 C6 117.90(13)
N1 C2 C3 122.55(14)
N1 C2 H2 118.7
C3 C2 H2 118.7
C4 C3 C2 118.89(14)
C4 C3 H3 120.6
C2 C3 H3 120.6
C3 C4 C5 119.53(15)
C3 C4 H4 120.2
C5 C4 H4 120.2
C6 C5 C4 118.51(15)
C6 C5 H5 120.7
C4 C5 H5 120.7
N1 C6 C5 122.62(14)
N1 C6 C7 117.46(13)
C5 C6 C7 119.92(13)
O8 C7 N9 123.55(14)
O8 C7 C6 121.43(13)
N9 C7 C6 115.02(13)
C7 N9 H9A 120.0
C7 N9 H9B 120.0
H9A N9 H9B 120.0
C12 N11 C16 117.15(14)
N11 C12 C13 123.70(15)
N11 C12 H12 118.2
C13 C12 H12 118.2
C14 C13 C12 118.41(15)
C14 C13 H13 120.8
C12 C13 H13 120.8
C13 C14 C15 119.05(15)
C13 C14 H14 120.5
C15 C14 H14 120.5
C16 C15 C14 118.33(15)
C16 C15 H15 120.8
C14 C15 H15 120.8
N11 C16 C15 123.36(14)
N11 C16 C17 117.54(13)
C15 C16 C17 119.10(14)
O18 C17 N19 124.03(15)
O18 C17 C16 119.13(14)
N19 C17 C16 116.83(14)
C17 N19 H19A 120.0
C17 N19 H19B 120.0
H19A N19 H19B 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.348(2)
N1 C6 1.360(2)
C2 C3 1.387(2)
C2 H2 0.9500
C3 C4 1.384(2)
C3 H3 0.9500
C4 C5 1.386(2)
C4 H4 0.9500
C5 C6 1.386(2)
C5 H5 0.9500
C6 C7 1.502(2)
C7 O8 1.2357(18)
C7 N9 1.3220(19)
N9 H9A 0.8800
N9 H9B 0.8800
N11 C12 1.337(2)
N11 C16 1.337(2)
C12 C13 1.385(2)
C12 H12 0.9500
C13 C14 1.377(2)
C13 H13 0.9500
C14 C15 1.388(2)
C14 H14 0.9500
C15 C16 1.387(2)
C15 H15 0.9500
C16 C17 1.505(2)
C17 O18 1.2415(19)
C17 N19 1.325(2)
N19 H19A 0.8800
N19 H19B 0.8800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N9 H9A O18 0.88 1.89 2.7518(17) 167.0 .
N19 H19A O8 0.88 2.13 2.9965(17) 167.8 .
N19 H19B O8 0.88 2.43 3.1450(18) 138.1 3
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
C6 N1 C2 C3 0.2(2)
N1 C2 C3 C4 -0.2(2)
C2 C3 C4 C5 0.1(2)
C3 C4 C5 C6 -0.1(2)
C2 N1 C6 C5 -0.1(2)
C2 N1 C6 C7 -179.85(13)
C4 C5 C6 N1 0.1(2)
C4 C5 C6 C7 179.81(14)
N1 C6 C7 O8 174.07(13)
C5 C6 C7 O8 -5.7(2)
N1 C6 C7 N9 -5.09(19)
C5 C6 C7 N9 175.18(13)
C16 N11 C12 C13 0.2(2)
N11 C12 C13 C14 -0.6(3)
C12 C13 C14 C15 0.2(2)
C13 C14 C15 C16 0.6(2)
C12 N11 C16 C15 0.6(2)
C12 N11 C16 C17 179.85(14)
C14 C15 C16 N11 -1.0(2)
C14 C15 C16 C17 179.75(15)
N11 C16 C17 O18 179.82(14)
C15 C16 C17 O18 -0.9(2)
N11 C16 C17 N19 1.0(2)
C15 C16 C17 N19 -179.75(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 69239512
