#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/43/7214361.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_7214361
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            'C12 H16 N2 O5'
_chemical_formula_weight         268.27
_chemical_name_common            '1:1 pico:adi'
_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                 106.06(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.006(2)
_cell_length_b                   20.510(6)
_cell_length_c                   9.125(3)
_cell_measurement_reflns_used    2578
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      4.27
_cell_volume                     1260.0(7)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9341
_diffrn_reflns_theta_full        66.58
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_min         4.31
_exptl_absorpt_coefficient_mu    0.938
_exptl_absorpt_correction_T_max  0.9634
_exptl_absorpt_correction_T_min  0.8721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.498
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.498
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1309P)²+3.3520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.1083
_reflns_number_gt                1894
_reflns_number_total             2213
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00265b2.cif
_cod_data_source_block           STC25a
_cod_depositor_comments
'Adding full bibliography for 7214357--7214365.cif.'
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7214361
#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+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
_atom_site_refinement_flags
N1 N 1.10590(19) -0.29575(6) -0.12737(14) 0.0157(3) Uani 1 1 d .
C2 C 1.2227(2) -0.33353(8) -0.18579(17) 0.0175(3) Uani 1 1 d .
H2 H 1.2082 -0.3795 -0.1809 0.021 Uiso 1 1 calc R
C3 C 1.3633(2) -0.30961(8) -0.25286(18) 0.0186(4) Uani 1 1 d .
H3 H 1.4424 -0.3385 -0.2927 0.022 Uiso 1 1 calc R
C4 C 1.3860(2) -0.24267(8) -0.26061(18) 0.0189(4) Uani 1 1 d .
H4 H 1.4814 -0.2246 -0.3053 0.023 Uiso 1 1 calc R
C5 C 1.2654(2) -0.20278(8) -0.20112(18) 0.0182(3) Uani 1 1 d .
H5 H 1.2767 -0.1567 -0.2049 0.022 Uiso 1 1 calc R
C6 C 1.1285(2) -0.23096(7) -0.13619(16) 0.0150(3) Uani 1 1 d .
C7 C 1.0006(2) -0.18632(7) -0.07224(17) 0.0154(3) Uani 1 1 d .
O8 O 1.03183(17) -0.12658(5) -0.07260(12) 0.0191(3) Uani 1 1 d .
N9 N 0.86075(19) -0.21219(6) -0.01800(15) 0.0181(3) Uani 1 1 d .
H9A H 0.7849 -0.1869 0.0200 0.022 Uiso 1 1 calc R
H9B H 0.8437 -0.2547 -0.0200 0.022 Uiso 1 1 calc R
O11 O 0.26170(17) 0.16249(5) 0.43110(14) 0.0226(3) Uani 1 1 d .
C12 C 0.1828(2) 0.10997(8) 0.43201(17) 0.0162(3) Uani 1 1 d .
C13 C 0.2380(2) 0.04896(7) 0.36278(17) 0.0161(4) Uani 1 1 d .
H13A H 0.1267 0.0364 0.2742 0.019 Uiso 1 1 calc R
H13B H 0.2580 0.0133 0.4386 0.019 Uiso 1 1 calc R
C14 C 0.4251(2) 0.05650(7) 0.31098(18) 0.0165(3) Uani 1 1 d .
H14A H 0.5355 0.0705 0.3988 0.020 Uiso 1 1 calc R
H14B H 0.4036 0.0912 0.2327 0.020 Uiso 1 1 calc R
C15 C 0.4845(2) -0.00644(7) 0.24499(18) 0.0162(3) Uani 1 1 d .
H15A H 0.5016 -0.0418 0.3214 0.019 Uiso 1 1 calc R
H15B H 0.3777 -0.0195 0.1537 0.019 Uiso 1 1 calc R
C16 C 0.6774(2) 0.00309(7) 0.20143(18) 0.0176(4) Uani 1 1 d .
H16A H 0.6614 0.0411 0.1321 0.021 Uiso 1 1 calc R
H16B H 0.7839 0.0139 0.2948 0.021 Uiso 1 1 calc R
C17 C 0.7442(2) -0.05419(7) 0.12557(17) 0.0153(3) Uani 1 1 d .
O18 O 0.65120(18) -0.10458(5) 0.09143(14) 0.0227(3) Uani 1 1 d .
O19 O 0.91533(17) -0.04254(5) 0.09649(13) 0.0206(3) Uani 1 1 d .
H19 H 0.9427 -0.0735 0.0456 0.031 Uiso 1 1 calc R
O20 O 0.03526(18) 0.10095(5) 0.49565(14) 0.0234(3) Uani 1 1 d .
H20 H 0.0076 0.1365 0.5306 0.035 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 116.96(13)
N1 C2 C3 123.92(15)
N1 C2 H2 118.0
C3 C2 H2 118.0
C2 C3 C4 118.63(14)
C2 C3 H3 120.7
C4 C3 H3 120.7
C3 C4 C5 118.16(15)
C3 C4 H4 120.9
C5 C4 H4 120.9
C6 C5 C4 119.29(15)
C6 C5 H5 120.4
C4 C5 H5 120.4
N1 C6 C5 123.03(14)
N1 C6 C7 119.05(13)
C5 C6 C7 117.92(14)
O8 C7 N9 122.96(14)
O8 C7 C6 118.25(13)
N9 C7 C6 118.79(14)
C7 N9 H9A 120.0
C7 N9 H9B 120.0
H9A N9 H9B 120.0
O11 C12 O20 122.49(14)
O11 C12 C13 124.58(14)
O20 C12 C13 112.93(13)
C12 C13 C14 113.03(13)
C12 C13 H13A 109.0
C14 C13 H13A 109.0
C12 C13 H13B 109.0
C14 C13 H13B 109.0
H13A C13 H13B 107.8
C13 C14 C15 112.87(13)
C13 C14 H14A 109.0
C15 C14 H14A 109.0
C13 C14 H14B 109.0
C15 C14 H14B 109.0
H14A C14 H14B 107.8
C16 C15 C14 110.62(13)
C16 C15 H15A 109.5
C14 C15 H15A 109.5
C16 C15 H15B 109.5
C14 C15 H15B 109.5
H15A C15 H15B 108.1
C17 C16 C15 115.57(13)
C17 C16 H16A 108.4
C15 C16 H16A 108.4
C17 C16 H16B 108.4
C15 C16 H16B 108.4
H16A C16 H16B 107.4
O18 C17 O19 123.69(14)
O18 C17 C16 124.75(14)
O19 C17 C16 111.53(13)
C17 O19 H19 109.5
C12 O20 H20 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.340(2)
N1 C6 1.343(2)
C2 C3 1.385(2)
C2 H2 0.9500
C3 C4 1.386(2)
C3 H3 0.9500
C4 C5 1.390(2)
C4 H4 0.9500
C5 C6 1.385(2)
C5 H5 0.9500
C6 C7 1.507(2)
C7 O8 1.245(2)
C7 N9 1.325(2)
N9 H9A 0.8800
N9 H9B 0.8800
O11 C12 1.212(2)
C12 O20 1.3312(19)
C12 C13 1.500(2)
C13 C14 1.519(2)
C13 H13A 0.9900
C13 H13B 0.9900
C14 C15 1.530(2)
C14 H14A 0.9900
C14 H14B 0.9900
C15 C16 1.523(2)
C15 H15A 0.9900
C15 H15B 0.9900
C16 C17 1.502(2)
C16 H16A 0.9900
C16 H16B 0.9900
C17 O18 1.215(2)
C17 O19 1.3196(19)
O19 H19 0.8400
O20 H20 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 O18 0.88 2.12 2.9724(18) 163.4 .
N9 H9B O11 0.88 2.10 2.8891(19) 148.6 2_645
O19 H19 O8 0.84 1.76 2.5912(15) 168.1 .
O20 H20 N1 0.84 1.93 2.7512(17) 164.9 2_655
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 0.3(2)
N1 C2 C3 C4 0.1(2)
C2 C3 C4 C5 -0.3(2)
C3 C4 C5 C6 0.3(2)
C2 N1 C6 C5 -0.4(2)
C2 N1 C6 C7 179.97(13)
C4 C5 C6 N1 0.1(2)
C4 C5 C6 C7 179.77(14)
N1 C6 C7 O8 175.54(14)
C5 C6 C7 O8 -4.2(2)
N1 C6 C7 N9 -4.3(2)
C5 C6 C7 N9 176.00(14)
O11 C12 C13 C14 8.7(2)
O20 C12 C13 C14 -171.53(13)
C12 C13 C14 C15 178.21(13)
C13 C14 C15 C16 -177.53(13)
C14 C15 C16 C17 -176.14(13)
C15 C16 C17 O18 3.8(2)
C15 C16 C17 O19 -177.89(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139198135
