#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/02/7200293.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_7200293
loop_
_publ_author_name
'Karki, Shyam'
'Friščić, Tomislav'
'Jones, William'
_publ_section_title
;
 Control and interconversion of cocrystal stoichiometry in grinding:
 stepwise mechanism for the formation of a hydrogen-bonded cocrystal
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              470
_journal_paper_doi               10.1039/b812531g
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C6 H6 N2 O, C8 H14 O4'
_chemical_formula_sum            'C14 H20 N2 O5'
_chemical_formula_weight         296.32
_chemical_name_common            'nicotinamide:suberic acid 1:1'
_chemical_name_systematic
;
nicotinamide:suberic acid 1:1
;
_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                 94.8320(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.95370(10)
_cell_length_b                   35.2893(6)
_cell_length_c                   8.7180(2)
_cell_measurement_reflns_used    16782
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      17.68
_cell_measurement_theta_min      1.02
_cell_volume                     1518.60(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4592
_diffrn_reflns_theta_full        17.68
_diffrn_reflns_theta_max         17.68
_diffrn_reflns_theta_min         3.72
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.026
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0290
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0446P)²+0.3752P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0734
_reflns_number_gt                898
_reflns_number_total             982
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b812531g.txt
_cod_data_source_block           (na).(sub)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7200293
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8745(4) 0.30154(4) 0.5036(2) 0.0333(5) Uani 1 1 d . . .
O2 O 1.1089(3) 0.33107(6) 0.8417(2) 0.0383(6) Uani 1 1 d . . .
O3 O 0.8785(4) 0.36826(5) 0.9903(2) 0.0427(6) Uani 1 1 d . . .
H3A H 0.796(5) 0.3439(8) 1.024(3) 0.051 Uiso 1 1 d . . .
O4 O 0.9483(4) 0.63639(7) 0.6097(2) 0.0468(6) Uani 1 1 d . . .
H4A H 1.019(5) 0.6576(8) 0.563(3) 0.056 Uiso 1 1 d . . .
O5 O 1.2895(4) 0.60294(5) 0.5314(2) 0.0541(7) Uani 1 1 d . . .
N1 N 0.6526(5) 0.19219(8) 0.5935(3) 0.0291(6) Uani 1 1 d . . .
N2 N 0.5293(4) 0.32696(7) 0.6187(2) 0.0344(6) Uani 1 1 d . . .
H2A H 0.5740 0.3500 0.5915 0.041 Uiso 1 1 calc R . .
H2B H 0.3884 0.3235 0.6722 0.041 Uiso 1 1 calc R . .
C1 C 0.4559(7) 0.18632(8) 0.6866(4) 0.0309(8) Uani 1 1 d . . .
H1 H 0.4096 0.1609 0.7095 0.037 Uiso 1 1 calc R . .
C2 C 0.3175(5) 0.21516(11) 0.7510(3) 0.0291(7) Uani 1 1 d . . .
H2 H 0.1782 0.2098 0.8162 0.035 Uiso 1 1 calc R . .
C3 C 0.3840(6) 0.25192(10) 0.7193(3) 0.0272(7) Uani 1 1 d . . .
H3 H 0.2906 0.2723 0.7623 0.033 Uiso 1 1 calc R . .
C4 C 0.5887(6) 0.25907(9) 0.6239(3) 0.0220(7) Uani 1 1 d . . .
C5 C 0.7155(5) 0.22805(12) 0.5635(3) 0.0274(7) Uani 1 1 d . . .
H5 H 0.8547 0.2326 0.4972 0.033 Uiso 1 1 calc R . .
C6 C 0.6733(6) 0.29770(9) 0.5794(3) 0.0255(7) Uani 1 1 d . . .
C7 C 1.0551(6) 0.36262(10) 0.8883(4) 0.0311(8) Uani 1 1 d . . .
C8 C 1.1882(5) 0.39811(8) 0.8376(3) 0.0415(8) Uani 1 1 d . . .
H8A H 1.2537 0.3934 0.7351 0.050 Uiso 1 1 calc R . .
H8B H 1.3491 0.4031 0.9100 0.050 Uiso 1 1 calc R . .
C9 C 1.0147(5) 0.43351(7) 0.8273(3) 0.0371(8) Uani 1 1 d . . .
H9A H 0.9519 0.4389 0.9299 0.044 Uiso 1 1 calc R . .
H9B H 0.8526 0.4288 0.7554 0.044 Uiso 1 1 calc R . .
C10 C 1.1632(5) 0.46801(8) 0.7729(3) 0.0428(8) Uani 1 1 d . . .
H10A H 1.3207 0.4733 0.8475 0.051 Uiso 1 1 calc R . .
H10B H 1.2335 0.4621 0.6727 0.051 Uiso 1 1 calc R . .
C11 C 0.9904(5) 0.50336(7) 0.7549(3) 0.0401(8) Uani 1 1 d . . .
H11A H 0.9286 0.5102 0.8564 0.048 Uiso 1 1 calc R . .
H11B H 0.8277 0.4977 0.6848 0.048 Uiso 1 1 calc R . .
C12 C 1.1358(5) 0.53713(7) 0.6923(3) 0.0407(8) Uani 1 1 d . . .
H12A H 1.3002 0.5426 0.7613 0.049 Uiso 1 1 calc R . .
H12B H 1.1945 0.5306 0.5898 0.049 Uiso 1 1 calc R . .
C13 C 0.9616(5) 0.57240(8) 0.6776(3) 0.0381(8) Uani 1 1 d . . .
H13A H 0.7877 0.5660 0.6191 0.046 Uiso 1 1 calc R . .
H13B H 0.9205 0.5805 0.7819 0.046 Uiso 1 1 calc R . .
C14 C 1.0868(8) 0.60482(9) 0.6002(3) 0.0331(8) Uani 1 1 d . . .
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'
O O 0.0106 0.0060 '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'
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
_geom_angle_publ_flag
C7 O3 H3A 112.2(14) . . ?
C14 O4 H4A 115.7(17) . . ?
C5 N1 C1 117.4(2) . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C1 C2 123.2(2) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C3 C2 C1 118.8(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 117.5(2) . . ?
C3 C4 C6 124.0(3) . . ?
C5 C4 C6 118.5(3) . . ?
N1 C5 C4 123.6(2) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
O1 C6 N2 121.8(3) . . ?
O1 C6 C4 119.5(3) . . ?
N2 C6 C4 118.7(3) . . ?
O2 C7 O3 122.6(3) . . ?
O2 C7 C8 123.3(3) . . ?
O3 C7 C8 114.0(3) . . ?
C7 C8 C9 116.4(2) . . ?
C7 C8 H8A 108.2 . . ?
C9 C8 H8A 108.2 . . ?
C7 C8 H8B 108.2 . . ?
C9 C8 H8B 108.2 . . ?
H8A C8 H8B 107.3 . . ?
C8 C9 C10 113.1(2) . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 114.1(2) . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 C12 113.8(2) . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 113.0(2) . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 114.4(2) . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
O5 C14 O4 122.4(3) . . ?
O5 C14 C13 125.1(3) . . ?
O4 C14 C13 112.5(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.249(3) . ?
O2 C7 1.222(3) . ?
O3 C7 1.314(3) . ?
O3 H3A 1.01(3) . ?
O4 C14 1.315(3) . ?
O4 H4A 0.93(3) . ?
O5 C14 1.214(3) . ?
N1 C5 1.334(3) . ?
N1 C1 1.336(3) . ?
N2 C6 1.317(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C1 C2 1.373(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.372(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(3) . ?
C4 C6 1.487(4) . ?
C5 H5 0.9500 . ?
C7 C8 1.499(4) . ?
C8 C9 1.515(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.519(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.513(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.518(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.514(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.490(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.3(3) . . . . ?
N1 C1 C2 C3 -0.3(3) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C2 C3 C4 C6 178.7(2) . . . . ?
C1 N1 C5 C4 0.2(3) . . . . ?
C3 C4 C5 N1 -0.7(3) . . . . ?
C6 C4 C5 N1 -178.8(2) . . . . ?
C3 C4 C6 O1 174.0(2) . . . . ?
C5 C4 C6 O1 -7.9(3) . . . . ?
C3 C4 C6 N2 -7.4(3) . . . . ?
C5 C4 C6 N2 170.7(2) . . . . ?
O2 C7 C8 C9 146.7(2) . . . . ?
O3 C7 C8 C9 -34.6(3) . . . . ?
C7 C8 C9 C10 -179.1(2) . . . . ?
C8 C9 C10 C11 177.4(2) . . . . ?
C9 C10 C11 C12 -176.9(2) . . . . ?
C10 C11 C12 C13 -179.0(2) . . . . ?
C11 C12 C13 C14 -173.4(2) . . . . ?
C12 C13 C14 O5 11.3(4) . . . . ?
C12 C13 C14 O4 -170.6(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653541
