#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/43/7214358.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_7214358
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            'C16 H18 N4 O6'
_chemical_formula_weight         362.34
_chemical_name_common            '2:1 pico:succ'
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 105.811(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   32.561(10)
_cell_length_b                   5.078(2)
_cell_length_c                   20.831(6)
_cell_measurement_reflns_used    7099
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.98
_cell_measurement_theta_min      4.54
_cell_volume                     3314.0(19)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'three-circle goniometer'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_source         'microfocus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16646
_diffrn_reflns_theta_full        66.53
_diffrn_reflns_theta_max         66.53
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    0.957
_exptl_absorpt_correction_T_max  0.9718
_exptl_absorpt_correction_T_min  0.8938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       0.0050(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.920
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0642P)²+3.9088P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1006
_reflns_number_gt                2566
_reflns_number_total             2896
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00265b2.cif
_cod_data_source_block           STC22a
_cod_depositor_comments
'Adding full bibliography for 7214357--7214365.cif.'
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7214358
#BEGIN Tags that were not found in dictionaries:
_chemical_source_common          EtOH
#END Tags that were not found in dictionaries
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'
'-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_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 0.17813(4) -0.0162(2) 1.30778(6) 0.0213(3) Uani 1 1 d .
C2 C 0.20422(5) 0.1864(3) 1.30718(7) 0.0228(3) Uani 1 1 d .
H2 H 0.2197 0.2600 1.3486 0.027 Uiso 1 1 calc R
C3 C 0.20982(4) 0.2944(3) 1.24900(7) 0.0208(3) Uani 1 1 d .
H3 H 0.2285 0.4396 1.2508 0.025 Uiso 1 1 calc R
C4 C 0.18789(4) 0.1882(3) 1.18844(7) 0.0211(3) Uani 1 1 d .
H4 H 0.1913 0.2581 1.1479 0.025 Uiso 1 1 calc R
C5 C 0.16066(4) -0.0230(3) 1.18780(7) 0.0200(3) Uani 1 1 d .
H5 H 0.1452 -0.1015 1.1470 0.024 Uiso 1 1 calc R
C6 C 0.15666(4) -0.1161(3) 1.24837(7) 0.0171(3) Uani 1 1 d .
C7 C 0.12640(4) -0.3372(3) 1.25013(7) 0.0171(3) Uani 1 1 d .
O8 O 0.10456(3) -0.4368(2) 1.19714(5) 0.0212(3) Uani 1 1 d .
N9 N 0.12419(4) -0.4110(3) 1.30991(6) 0.0224(3) Uani 1 1 d .
H9A H 0.1065 -0.5373 1.3139 0.027 Uiso 1 1 calc R
H9B H 0.1404 -0.3338 1.3458 0.027 Uiso 1 1 calc R
C11 C 0.01305(5) -1.1463(3) 1.22469(7) 0.0217(3) Uani 1 1 d .
H11A H 0.0290 -1.3139 1.2282 0.026 Uiso 1 1 calc R
H11B H -0.0065 -1.1352 1.1791 0.026 Uiso 1 1 calc R
C12 C 0.04398(4) -0.9197(3) 1.23550(7) 0.0193(3) Uani 1 1 d .
O13 O 0.05812(4) -0.8145(2) 1.28967(5) 0.0286(3) Uani 1 1 d .
O14 O 0.05450(3) -0.8467(2) 1.18139(5) 0.0233(3) Uani 1 1 d .
H14 H 0.0720 -0.7215 1.1907 0.035 Uiso 1 1 calc R
N21 N 0.06409(4) 0.3617(2) 0.92152(6) 0.0198(3) Uani 1 1 d .
C22 C 0.03582(5) 0.5533(3) 0.91979(7) 0.0218(3) Uani 1 1 d .
H22 H 0.0154 0.5892 0.8785 0.026 Uiso 1 1 calc R
C23 C 0.03452(5) 0.7032(3) 0.97489(7) 0.0224(3) Uani 1 1 d .
H23 H 0.0139 0.8388 0.9710 0.027 Uiso 1 1 calc R
C24 C 0.06380(5) 0.6521(3) 1.03559(7) 0.0221(3) Uani 1 1 d .
H24 H 0.0634 0.7496 1.0743 0.027 Uiso 1 1 calc R
C25 C 0.09377(4) 0.4542(3) 1.03834(7) 0.0199(3) Uani 1 1 d .
H25 H 0.1145 0.4147 1.0790 0.024 Uiso 1 1 calc R
C26 C 0.09272(4) 0.3160(3) 0.98064(7) 0.0171(3) Uani 1 1 d .
C27 C 0.12466(4) 0.1018(3) 0.98138(7) 0.0169(3) Uani 1 1 d .
O28 O 0.15353(3) 0.0590(2) 1.03351(5) 0.0205(3) Uani 1 1 d .
N29 N 0.12025(4) -0.0322(2) 0.92546(6) 0.0198(3) Uani 1 1 d .
H29A H 0.1383 -0.1594 0.9237 0.024 Uiso 1 1 calc R
H29B H 0.0993 0.0058 0.8900 0.024 Uiso 1 1 calc R
C31 C 0.24720(4) -0.6687(3) 1.02901(7) 0.0203(3) Uani 1 1 d .
H31A H 0.2418 -0.7883 1.0633 0.024 Uiso 1 1 calc R
H31B H 0.2740 -0.5722 1.0493 0.024 Uiso 1 1 calc R
C32 C 0.21107(4) -0.4740(3) 1.00883(7) 0.0187(3) Uani 1 1 d .
O33 O 0.18771(3) -0.4512(2) 0.95256(5) 0.0228(3) Uani 1 1 d .
O34 O 0.20775(3) -0.3274(2) 1.05966(5) 0.0245(3) Uani 1 1 d .
H34 H 0.1882 -0.2163 1.0463 0.029 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 N1 C6 117.01(12) . .
N1 C2 C3 123.24(13) . .
N1 C2 H2 118.4 . .
C3 C2 H2 118.4 . .
C4 C3 C2 119.07(14) . .
C4 C3 H3 120.5 . .
C2 C3 H3 120.5 . .
C3 C4 C5 118.75(13) . .
C3 C4 H4 120.6 . .
C5 C4 H4 120.6 . .
C6 C5 C4 118.18(13) . .
C6 C5 H5 120.9 . .
C4 C5 H5 120.9 . .
N1 C6 C5 123.74(13) . .
N1 C6 C7 116.10(12) . .
C5 C6 C7 120.15(12) . .
O8 C7 N9 123.73(13) . .
O8 C7 C6 120.15(12) . .
N9 C7 C6 116.10(12) . .
C7 N9 H9A 120.0 . .
C7 N9 H9B 120.0 . .
H9A N9 H9B 120.0 . .
C12 C11 C11 111.91(11) . 2_557
C12 C11 H11A 109.2 . .
C11 C11 H11A 109.2 2_557 .
C12 C11 H11B 109.2 . .
C11 C11 H11B 109.2 2_557 .
H11A C11 H11B 107.9 . .
O13 C12 O14 123.22(14) . .
O13 C12 C11 122.80(13) . .
O14 C12 C11 113.98(12) . .
C12 O14 H14 109.5 . .
C22 N21 C26 116.82(12) . .
N21 C22 C23 123.68(13) . .
N21 C22 H22 118.2 . .
C23 C22 H22 118.2 . .
C24 C23 C22 118.93(13) . .
C24 C23 H23 120.5 . .
C22 C23 H23 120.5 . .
C23 C24 C25 118.27(13) . .
C23 C24 H24 120.9 . .
C25 C24 H24 120.9 . .
C26 C25 C24 118.65(13) . .
C26 C25 H25 120.7 . .
C24 C25 H25 120.7 . .
N21 C26 C25 123.63(13) . .
N21 C26 C27 116.04(12) . .
C25 C26 C27 120.33(12) . .
O28 C27 N29 123.56(13) . .
O28 C27 C26 119.39(12) . .
N29 C27 C26 117.05(12) . .
C27 N29 H29A 120.0 . .
C27 N29 H29B 120.0 . .
H29A N29 H29B 120.0 . .
C32 C31 C31 112.94(15) . 7_537
C32 C31 H31A 109.0 . .
C31 C31 H31A 109.0 7_537 .
C32 C31 H31B 109.0 . .
C31 C31 H31B 109.0 7_537 .
H31A C31 H31B 107.8 . .
O33 C32 O34 123.49(13) . .
O33 C32 C31 124.55(13) . .
O34 C32 C31 111.96(11) . .
C32 O34 H34 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.336(2) .
N1 C6 1.3439(19) .
C2 C3 1.387(2) .
C2 H2 0.9500 .
C3 C4 1.379(2) .
C3 H3 0.9500 .
C4 C5 1.389(2) .
C4 H4 0.9500 .
C5 C6 1.386(2) .
C5 H5 0.9500 .
C6 C7 1.501(2) .
C7 O8 1.2459(17) .
C7 N9 1.3212(19) .
N9 H9A 0.8800 .
N9 H9B 0.8800 .
C11 C12 1.505(2) .
C11 C11 1.524(3) 2_557
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 O13 1.2196(18) .
C12 O14 1.3174(18) .
O14 H14 0.8400 .
N21 C22 1.3329(19) .
N21 C26 1.3470(18) .
C22 C23 1.387(2) .
C22 H22 0.9500 .
C23 C24 1.385(2) .
C23 H23 0.9500 .
C24 C25 1.391(2) .
C24 H24 0.9500 .
C25 C26 1.384(2) .
C25 H25 0.9500 .
C26 C27 1.502(2) .
C27 O28 1.2466(17) .
C27 N29 1.3226(18) .
N29 H29A 0.8800 .
N29 H29B 0.8800 .
C31 C32 1.506(2) .
C31 C31 1.515(3) 7_537
C31 H31A 0.9900 .
C31 H31B 0.9900 .
C32 O33 1.2164(17) .
C32 O34 1.3226(17) .
O34 H34 0.8400 .
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 O13 0.88 2.07 2.9172(18) 161.1 .
N9 H9B O33 0.88 2.58 3.2014(18) 128.5 6_546
N9 H9B N29 0.88 2.69 3.3231(19) 129.9 6_556
O14 H14 O8 0.84 1.78 2.6087(16) 170.6 .
N29 H29A O33 0.88 2.15 2.9991(17) 162.1 .
N29 H29B O13 0.88 2.36 3.0955(18) 140.9 6_545
O34 H34 O28 0.84 1.77 2.5959(15) 167.2 .
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
_geom_torsion_site_symmetry_1
C6 N1 C2 C3 0.0(2) .
N1 C2 C3 C4 -0.6(2) .
C2 C3 C4 C5 0.4(2) .
C3 C4 C5 C6 0.4(2) .
C2 N1 C6 C5 0.9(2) .
C2 N1 C6 C7 -177.92(12) .
C4 C5 C6 N1 -1.1(2) .
C4 C5 C6 C7 177.71(12) .
N1 C6 C7 O8 178.41(12) .
C5 C6 C7 O8 -0.4(2) .
N1 C6 C7 N9 -0.24(18) .
C5 C6 C7 N9 -179.09(13) .
C11 C11 C12 O13 25.9(2) 2_557
C11 C11 C12 O14 -154.38(13) 2_557
C26 N21 C22 C23 -0.3(2) .
N21 C22 C23 C24 -0.6(2) .
C22 C23 C24 C25 1.0(2) .
C23 C24 C25 C26 -0.6(2) .
C22 N21 C26 C25 0.6(2) .
C22 N21 C26 C27 -179.25(12) .
C24 C25 C26 N21 -0.2(2) .
C24 C25 C26 C27 179.69(13) .
N21 C26 C27 O28 176.05(12) .
C25 C26 C27 O28 -3.8(2) .
N21 C26 C27 N29 -3.93(18) .
C25 C26 C27 N29 176.18(13) .
C31 C31 C32 O33 1.9(2) 7_537
C31 C31 C32 O34 -177.61(15) 7_537
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139198132
