#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/02/7200295.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_7200295
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_absolute_configuration
;
1133 Friedel pairs were averaged for the refinement.
;
_chemical_formula_moiety         'C6 H6 N2 O, C9 H16 O4'
_chemical_formula_sum            'C15 H22 N2 O5'
_chemical_formula_weight         310.35
_chemical_name_common            'nicotinamide:azelaic acid 2:1'
_chemical_name_systematic
;
nicotinamide:azelaic acid 2:1
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.64550(10)
_cell_length_b                   36.5695(6)
_cell_length_c                   5.20210(10)
_cell_measurement_reflns_used    23872
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1644.70(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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            10952
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.65
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.937
_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    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2082
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0408
_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)+(0.0489P)²+0.3144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1065
_reflns_number_gt                1620
_reflns_number_total             2082
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b812531g.txt
_cod_data_source_block           (na).(aze)
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               7200295
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
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 0.5529(2) 0.29892(4) 1.7504(4) 0.0482(5) Uani 1 1 d . . .
O2 O 0.8911(2) 0.32755(5) 0.9865(4) 0.0569(5) Uani 1 1 d . . .
O3 O 1.0730(2) 0.36331(5) 0.8246(4) 0.0591(6) Uani 1 1 d . . .
H3A H 1.099(3) 0.3397(8) 0.699(8) 0.071 Uiso 1 1 d . . .
O4 O 0.5358(2) 0.63839(5) 1.4411(4) 0.0567(6) Uani 1 1 d . . .
H4A H 0.501(3) 0.6583(8) 1.365(7) 0.068 Uiso 1 1 d . . .
O5 O 0.4916(3) 0.61078(5) 1.0708(5) 0.0814(8) Uani 1 1 d . . .
N1 N 0.6523(2) 0.19274(5) 1.5445(4) 0.0427(5) Uani 1 1 d . . .
N2 N 0.6582(3) 0.32234(6) 1.3924(5) 0.0508(6) Uani 1 1 d . . .
H2A H 0.6297 0.3446 1.4347 0.061 Uiso 1 1 calc R . .
H2B H 0.7091 0.3185 1.2484 0.061 Uiso 1 1 calc R . .
C1 C 0.6173(3) 0.22752(6) 1.6029(5) 0.0402(6) Uani 1 1 d . . .
H1 H 0.5520 0.2320 1.7463 0.048 Uiso 1 1 calc R . .
C2 C 0.6717(2) 0.25702(6) 1.4645(5) 0.0354(5) Uani 1 1 d . . .
C3 C 0.7644(3) 0.25031(7) 1.2537(6) 0.0427(6) Uani 1 1 d . . .
H3 H 0.8025 0.2700 1.1524 0.051 Uiso 1 1 calc R . .
C4 C 0.8013(3) 0.21440(7) 1.1918(6) 0.0471(7) Uani 1 1 d . . .
H4 H 0.8653 0.2091 1.0482 0.057 Uiso 1 1 calc R . .
C5 C 0.7436(3) 0.18687(7) 1.3421(5) 0.0446(6) Uani 1 1 d . . .
H5 H 0.7699 0.1624 1.3001 0.053 Uiso 1 1 calc R . .
C6 C 0.6248(3) 0.29467(6) 1.5448(5) 0.0397(6) Uani 1 1 d . . .
C7 C 0.9621(3) 0.35611(7) 0.9877(6) 0.0484(7) Uani 1 1 d . . .
C8 C 0.9335(4) 0.38615(7) 1.1786(7) 0.0622(9) Uani 1 1 d . . .
H8A H 1.0316 0.3919 1.2681 0.075 Uiso 1 1 calc R . .
H8B H 0.8588 0.3774 1.3091 0.075 Uiso 1 1 calc R . .
C9 C 0.8717(3) 0.42045(7) 1.0568(7) 0.0595(8) Uani 1 1 d . . .
H9A H 0.7771 0.4145 0.9584 0.071 Uiso 1 1 calc R . .
H9B H 0.9493 0.4301 0.9345 0.071 Uiso 1 1 calc R . .
C10 C 0.8338(3) 0.44995(7) 1.2552(7) 0.0571(8) Uani 1 1 d . . .
H10A H 0.7563 0.4402 1.3773 0.068 Uiso 1 1 calc R . .
H10B H 0.9285 0.4557 1.3540 0.068 Uiso 1 1 calc R . .
C11 C 0.7717(4) 0.48484(7) 1.1384(7) 0.0646(9) Uani 1 1 d . . .
H11A H 0.6792 0.4789 1.0345 0.078 Uiso 1 1 calc R . .
H11B H 0.8507 0.4950 1.0206 0.078 Uiso 1 1 calc R . .
C12 C 0.7284(3) 0.51397(6) 1.3327(7) 0.0528(7) Uani 1 1 d . . .
H12A H 0.6533 0.5035 1.4561 0.063 Uiso 1 1 calc R . .
H12B H 0.8221 0.5210 1.4305 0.063 Uiso 1 1 calc R . .
C13 C 0.6590(4) 0.54794(7) 1.2139(7) 0.0567(8) Uani 1 1 d . . .
H13A H 0.7332 0.5580 1.0871 0.068 Uiso 1 1 calc R . .
H13B H 0.5641 0.5410 1.1196 0.068 Uiso 1 1 calc R . .
C14 C 0.6189(3) 0.57764(6) 1.4039(6) 0.0474(7) Uani 1 1 d . . .
H14A H 0.5490 0.5673 1.5361 0.057 Uiso 1 1 calc R . .
H14B H 0.7147 0.5856 1.4916 0.057 Uiso 1 1 calc R . .
C15 C 0.5428(3) 0.61031(6) 1.2854(6) 0.0449(6) 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O3 H3A 112.0(16) . . ?
C15 O4 H4A 113(2) . . ?
C5 N1 C1 117.7(2) . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C1 C2 123.1(2) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 118.3(2) . . ?
C1 C2 C6 118.8(2) . . ?
C3 C2 C6 122.9(2) . . ?
C2 C3 C4 119.0(2) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C4 123.3(2) . . ?
N1 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
O1 C6 N2 122.0(2) . . ?
O1 C6 C2 119.3(2) . . ?
N2 C6 C2 118.7(2) . . ?
O2 C7 O3 122.8(3) . . ?
O2 C7 C8 123.4(3) . . ?
O3 C7 C8 113.7(2) . . ?
C7 C8 C9 113.0(3) . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 C10 112.4(3) . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 113.6(3) . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 C12 114.4(3) . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C11 113.8(3) . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 114.5(3) . . ?
C14 C13 H13A 108.6 . . ?
C12 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C13 113.9(3) . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
O5 C15 O4 123.1(2) . . ?
O5 C15 C14 123.8(2) . . ?
O4 C15 C14 113.1(2) . . ?
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 1.246(3) . ?
O2 C7 1.211(3) . ?
O3 C7 1.307(3) . ?
O3 H3A 1.11(3) . ?
O4 C15 1.309(3) . ?
O4 H4A 0.88(3) . ?
O5 C15 1.201(4) . ?
N1 C5 1.334(3) . ?
N1 C1 1.342(3) . ?
N2 C6 1.317(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C1 C2 1.380(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.380(4) . ?
C2 C6 1.495(3) . ?
C3 C4 1.389(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.369(4) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C7 C8 1.501(4) . ?
C8 C9 1.503(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.529(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.512(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.515(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.512(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.509(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.496(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 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(4) . . . . ?
N1 C1 C2 C3 1.1(4) . . . . ?
N1 C1 C2 C6 179.6(2) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C6 C2 C3 C4 -179.5(3) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C1 N1 C5 C4 -0.6(4) . . . . ?
C3 C4 C5 N1 0.6(4) . . . . ?
C1 C2 C6 O1 8.2(4) . . . . ?
C3 C2 C6 O1 -173.4(2) . . . . ?
C1 C2 C6 N2 -170.5(2) . . . . ?
C3 C2 C6 N2 8.0(4) . . . . ?
O2 C7 C8 C9 -114.7(3) . . . . ?
O3 C7 C8 C9 66.3(4) . . . . ?
C7 C8 C9 C10 176.4(2) . . . . ?
C8 C9 C10 C11 179.8(3) . . . . ?
C9 C10 C11 C12 178.1(3) . . . . ?
C10 C11 C12 C13 -177.1(3) . . . . ?
C11 C12 C13 C14 -178.6(3) . . . . ?
C12 C13 C14 C15 -177.0(2) . . . . ?
C13 C14 C15 O5 13.2(4) . . . . ?
C13 C14 C15 O4 -167.6(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653542
