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#$Date: 2016-03-26 16:19:56 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180333 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/02/7200294.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_7200294
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         'C8 H14 O4, 2(C6 H6 N2 O)'
_chemical_formula_sum            'C20 H26 N4 O6'
_chemical_formula_weight         418.45
_chemical_name_common            'nicotinamide:suberic acid 2:1'
_chemical_name_systematic
;
nicotinamide:suberic 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                93.062(3)
_cell_angle_beta                 94.810(3)
_cell_angle_gamma                90.740(2)
_cell_formula_units_Z            1
_cell_length_a                   5.0288(3)
_cell_length_b                   5.4403(3)
_cell_length_c                   18.7537(11)
_cell_measurement_reflns_used    7216
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      1.02
_cell_volume                     510.45(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 0.965
_diffrn_measured_fraction_theta_max 0.965
_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  0.0574
_diffrn_reflns_av_sigmaI/netI    0.1063
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_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            6237
_diffrn_reflns_theta_full        29.90
_diffrn_reflns_theta_max         29.90
_diffrn_reflns_theta_min         3.75
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.000
_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    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             222
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1719
_refine_ls_R_factor_gt           0.0800
_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)+(0.0390P)²+0.4980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1764
_reflns_number_gt                1495
_reflns_number_total             2848
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b812531g.txt
_cod_data_source_block           (na)2.(sub)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7200294
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 0.3238(4) 0.8094(4) 0.06122(10) 0.0346(5) Uani 1 1 d . . .
N1 N 0.4762(5) 0.3822(4) 0.23700(12) 0.0338(6) Uani 1 1 d . . .
C1 C 0.6664(6) 0.2140(5) 0.23297(15) 0.0339(7) Uani 1 1 d . . .
H1 H 0.6875 0.0996 0.2695 0.041 Uiso 1 1 calc R . .
O2 O 0.1720(4) 0.4321(4) 0.34786(11) 0.0402(6) Uani 1 1 d . . .
H2C H 0.268(7) 0.414(6) 0.3054(18) 0.048 Uiso 1 1 d . . .
N2 N 0.7489(4) 0.7813(4) 0.03355(12) 0.0319(6) Uani 1 1 d . . .
H2A H 0.7240 0.8878 0.0000 0.038 Uiso 1 1 calc R . .
H2B H 0.9065 0.7152 0.0420 0.038 Uiso 1 1 calc R . .
C2 C 0.8330(6) 0.1991(5) 0.17841(15) 0.0320(7) Uani 1 1 d . . .
H2 H 0.9673 0.0780 0.1776 0.038 Uiso 1 1 calc R . .
O3 O 0.0027(4) 0.7642(4) 0.29671(11) 0.0427(6) Uani 1 1 d . . .
C3 C 0.8015(5) 0.3630(5) 0.12484(14) 0.0288(6) Uani 1 1 d . . .
H3 H 0.9141 0.3560 0.0866 0.035 Uiso 1 1 calc R . .
C4 C 0.6037(5) 0.5382(5) 0.12731(14) 0.0252(6) Uani 1 1 d . . .
C5 C 0.4468(5) 0.5417(5) 0.18487(14) 0.0303(6) Uani 1 1 d . . .
H5 H 0.3127 0.6625 0.1875 0.036 Uiso 1 1 calc R . .
C6 C 0.5484(5) 0.7202(5) 0.07154(14) 0.0277(6) Uani 1 1 d . . .
C7 C 0.0131(6) 0.6239(5) 0.34517(15) 0.0323(7) Uani 1 1 d . . .
C8 C -0.1492(6) 0.6428(6) 0.40875(16) 0.0381(7) Uani 1 1 d . . .
H8A H -0.0287 0.6184 0.4522 0.046 Uiso 1 1 calc R . .
H8B H -0.2815 0.5053 0.4039 0.046 Uiso 1 1 calc R . .
C9 C -0.2966(6) 0.8793(5) 0.42075(15) 0.0345(7) Uani 1 1 d . . .
H9A H -0.4348 0.8969 0.3806 0.041 Uiso 1 1 calc R . .
H9B H -0.1702 1.0207 0.4218 0.041 Uiso 1 1 calc R . .
C10 C -0.4284(6) 0.8815(5) 0.49129(16) 0.0361(7) Uani 1 1 d . . .
H10A H -0.5583 0.7424 0.4891 0.043 Uiso 1 1 calc R . .
H10B H -0.2899 0.8548 0.5307 0.043 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'
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
C1 N1 C5 118.0(2) . . ?
N1 C1 C2 123.0(3) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C7 O2 H2C 111.3(19) . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C1 C2 C3 118.8(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 119.4(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 117.8(2) . . ?
C3 C4 C6 123.9(2) . . ?
C5 C4 C6 118.3(2) . . ?
N1 C5 C4 122.9(3) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
O1 C6 N2 121.8(2) . . ?
O1 C6 C4 120.8(2) . . ?
N2 C6 C4 117.3(2) . . ?
O3 C7 O2 123.4(3) . . ?
O3 C7 C8 125.3(3) . . ?
O2 C7 C8 111.3(2) . . ?
C7 C8 C9 117.0(2) . . ?
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 110.8(2) . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C10 C10 C9 114.0(3) 2_476 . ?
C10 C10 H10A 108.8 2_476 . ?
C9 C10 H10A 108.8 . . ?
C10 C10 H10B 108.8 2_476 . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 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 1.239(3) . ?
N1 C1 1.336(4) . ?
N1 C5 1.342(3) . ?
C1 C2 1.375(4) . ?
C1 H1 0.9500 . ?
O2 C7 1.323(3) . ?
O2 H2C 0.97(3) . ?
N2 C6 1.331(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C2 C3 1.379(4) . ?
C2 H2 0.9500 . ?
O3 C7 1.216(3) . ?
C3 C4 1.389(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(4) . ?
C4 C6 1.490(4) . ?
C5 H5 0.9500 . ?
C7 C8 1.500(4) . ?
C8 C9 1.509(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.528(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C10 1.518(6) 2_476 ?
C10 H10A 0.9900 . ?
C10 H10B 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 0.5(4) . . . . ?
N1 C1 C2 C3 -0.7(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C2 C3 C4 C6 -178.6(3) . . . . ?
C1 N1 C5 C4 0.3(4) . . . . ?
C3 C4 C5 N1 -0.9(4) . . . . ?
C6 C4 C5 N1 178.4(2) . . . . ?
C3 C4 C6 O1 154.0(3) . . . . ?
C5 C4 C6 O1 -25.3(4) . . . . ?
C3 C4 C6 N2 -25.8(4) . . . . ?
C5 C4 C6 N2 154.9(3) . . . . ?
O3 C7 C8 C9 -12.3(5) . . . . ?
O2 C7 C8 C9 167.9(3) . . . . ?
C7 C8 C9 C10 -174.1(3) . . . . ?
C8 C9 C10 C10 177.6(3) . . . 2_476 ?
