#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:19:56 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180333 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/02/7200296.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_7200296
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         'C10 H18 O4, 2(C6 H6 O2 N)'
_chemical_formula_sum            'C22 H30 N4 O6'
_chemical_formula_weight         446.50
_chemical_name_common            'nicotinamide:sebacic acid 2:1'
_chemical_name_systematic
;
nicotinamide:sebacic acid 2:1
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                89.354(2)
_cell_angle_beta                 84.241(2)
_cell_angle_gamma                89.872(2)
_cell_formula_units_Z            1
_cell_length_a                   5.0365(2)
_cell_length_b                   5.4470(2)
_cell_length_c                   20.5004(9)
_cell_measurement_reflns_used    7012
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     559.53(4)
_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 0.979
_diffrn_measured_fraction_theta_max 0.979
_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  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5593
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         3.74
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.018
_exptl_absorpt_correction_T_min  0.909
_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    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             238
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0427P)²+0.2549P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1267
_reflns_number_gt                1906
_reflns_number_total             2529
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b812531g.txt
_cod_data_source_block           (na)2.(seb)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7200296
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.7843(2) 0.7969(2) 0.05643(6) 0.0391(3) Uani 1 1 d . . .
O2 O 0.4426(3) 0.3510(3) 0.31871(6) 0.0462(4) Uani 1 1 d . . .
H2C H 0.577(5) 0.351(4) 0.2820(11) 0.055 Uiso 1 1 d . . .
O3 O 0.3062(3) 0.6954(3) 0.27232(6) 0.0488(4) Uani 1 1 d . . .
N1 N 0.8225(3) 0.3287(3) 0.21691(7) 0.0382(4) Uani 1 1 d . . .
N2 N 1.2293(3) 0.7742(3) 0.03105(7) 0.0345(3) Uani 1 1 d . . .
H2A H 1.2262 0.8880 0.0003 0.041 Uiso 1 1 calc R . .
H2B H 1.3816 0.7058 0.0388 0.041 Uiso 1 1 calc R . .
C1 C 1.0181(4) 0.1607(3) 0.21321(9) 0.0375(4) Uani 1 1 d . . .
H1 H 1.0160 0.0379 0.2465 0.045 Uiso 1 1 calc R . .
C2 C 1.2221(4) 0.1587(3) 0.16308(9) 0.0371(4) Uani 1 1 d . . .
H2 H 1.3585 0.0377 0.1622 0.044 Uiso 1 1 calc R . .
C3 C 1.2252(3) 0.3359(3) 0.11405(8) 0.0338(4) Uani 1 1 d . . .
H3 H 1.3640 0.3386 0.0791 0.041 Uiso 1 1 calc R . .
C4 C 1.0220(3) 0.5099(3) 0.11678(8) 0.0290(4) Uani 1 1 d . . .
C5 C 0.8266(3) 0.4988(3) 0.16937(8) 0.0341(4) Uani 1 1 d . . .
H5 H 0.6884 0.6183 0.1717 0.041 Uiso 1 1 calc R . .
C6 C 1.0031(3) 0.7052(3) 0.06582(8) 0.0296(4) Uani 1 1 d . . .
C7 C 0.2848(4) 0.5456(3) 0.31641(8) 0.0350(4) Uani 1 1 d . . .
C8 C 0.0770(4) 0.5505(3) 0.37427(9) 0.0416(5) Uani 1 1 d . . .
H8A H 0.1656 0.5125 0.4142 0.050 Uiso 1 1 calc R . .
H8B H -0.0523 0.4172 0.3691 0.050 Uiso 1 1 calc R . .
C9 C -0.0776(4) 0.7878(3) 0.38554(9) 0.0376(4) Uani 1 1 d . . .
H9A H -0.1879 0.8172 0.3489 0.045 Uiso 1 1 calc R . .
H9B H 0.0489 0.9263 0.3865 0.045 Uiso 1 1 calc R . .
C10 C -0.2569(4) 0.7774(3) 0.44985(9) 0.0409(4) Uani 1 1 d . . .
H10A H -0.3855 0.6413 0.4476 0.049 Uiso 1 1 calc R . .
H10B H -0.1451 0.7373 0.4856 0.049 Uiso 1 1 calc R . .
C11 C -0.4120(4) 1.0098(3) 0.46770(8) 0.0396(4) Uani 1 1 d . . .
H11A H -0.5253 1.0505 0.4323 0.047 Uiso 1 1 calc R . .
H11B H -0.2845 1.1466 0.4704 0.047 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 0.0033 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 O2 H2C 110.9(13) . . ?
C5 N1 C1 117.95(15) . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C1 C2 122.75(15) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C1 C2 C3 118.96(16) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 119.00(15) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 117.95(15) . . ?
C5 C4 C6 118.69(14) . . ?
C3 C4 C6 123.35(14) . . ?
N1 C5 C4 123.38(15) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
O1 C6 N2 122.06(15) . . ?
O1 C6 C4 120.65(14) . . ?
N2 C6 C4 117.29(14) . . ?
O3 C7 O2 123.37(16) . . ?
O3 C7 C8 125.24(16) . . ?
O2 C7 C8 111.37(14) . . ?
C7 C8 C9 116.66(15) . . ?
C7 C8 H8A 108.1 . . ?
C9 C8 H8A 108.1 . . ?
C7 C8 H8B 108.1 . . ?
C9 C8 H8B 108.1 . . ?
H8A C8 H8B 107.3 . . ?
C8 C9 C10 111.00(14) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 115.57(15) . . ?
C11 C10 H10A 108.4 . . ?
C9 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.4 . . ?
C10 C11 C11 113.56(18) . 2_476 ?
C10 C11 H11A 108.9 . . ?
C11 C11 H11A 108.9 2_476 . ?
C10 C11 H11B 108.9 . . ?
C11 C11 H11B 108.9 2_476 . ?
H11A C11 H11B 107.7 . . ?
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 1.2406(19) . ?
O2 C7 1.327(2) . ?
O2 H2C 0.96(2) . ?
O3 C7 1.208(2) . ?
N1 C5 1.336(2) . ?
N1 C1 1.340(2) . ?
N2 C6 1.334(2) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C1 C2 1.379(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.385(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 C6 1.492(2) . ?
C5 H5 0.9500 . ?
C7 C8 1.502(2) . ?
C8 C9 1.515(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.522(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.515(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C11 1.520(3) 2_476 ?
C11 H11A 0.9900 . ?
C11 H11B 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 0.7(3) . . . . ?
N1 C1 C2 C3 -0.6(3) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C2 C3 C4 C6 -178.66(16) . . . . ?
C1 N1 C5 C4 0.0(3) . . . . ?
C3 C4 C5 N1 -0.7(3) . . . . ?
C6 C4 C5 N1 178.77(17) . . . . ?
C5 C4 C6 O1 -25.3(2) . . . . ?
C3 C4 C6 O1 154.08(18) . . . . ?
C5 C4 C6 N2 155.14(16) . . . . ?
C3 C4 C6 N2 -25.5(2) . . . . ?
O3 C7 C8 C9 -13.9(3) . . . . ?
O2 C7 C8 C9 167.34(17) . . . . ?
C7 C8 C9 C10 -173.31(17) . . . . ?
C8 C9 C10 C11 177.35(18) . . . . ?
C9 C10 C11 C11 180.0(2) . . . 2_476 ?
