#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/02/7200292.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_7200292
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         'C7 H12 O4, C6 H6 N2 O'
_chemical_formula_sum            'C13 H18 N2 O5'
_chemical_formula_weight         282.29
_chemical_name_common            'nicotinamide:pimelic acid 1:1'
_chemical_name_systematic
;
nicotinamide:pimelic acid 1:1
;
_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                99.568(2)
_cell_angle_beta                 94.075(2)
_cell_angle_gamma                104.177(2)
_cell_formula_units_Z            2
_cell_length_a                   5.4425(1)
_cell_length_b                   7.3981(2)
_cell_length_c                   17.9304(6)
_cell_measurement_reflns_used    4820
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      1.00
_cell_volume                     685.49(3)
_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 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6741
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         4.04
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.931
_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    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2390
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0346
_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)+(0.0494P)²+0.1547P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0961
_reflns_number_gt                2156
_reflns_number_total             2390
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b812531g.txt
_cod_data_source_block           (na).(pim)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7200292
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 0.84889(17) 0.67931(13) -0.01703(5) 0.0352(2) Uani 1 1 d . . .
O2 O 0.12418(17) 0.24623(13) 0.15366(5) 0.0347(2) Uani 1 1 d . . .
H21 H 0.116(3) 0.257(2) 0.1048(10) 0.042 Uiso 1 1 d . . .
O3 O -0.27450(17) 0.06694(13) 0.12325(5) 0.0356(2) Uani 1 1 d . . .
O4 O 0.76909(17) 0.31321(15) 0.56772(5) 0.0405(3) Uani 1 1 d . . .
O5 O 0.47908(19) 0.21731(15) 0.64443(5) 0.0398(3) Uani 1 1 d . . .
H51 H 0.616(3) 0.243(2) 0.6788(11) 0.048 Uiso 1 1 d . . .
N1 N 1.1312(2) 0.70168(15) 0.24309(6) 0.0289(3) Uani 1 1 d . . .
N2 N 1.2447(2) 0.85115(19) 0.02929(7) 0.0474(4) Uani 1 1 d . . .
H2A H 1.2737 0.8840 -0.0149 0.057 Uiso 1 1 calc R . .
H2B H 1.3643 0.8924 0.0683 0.057 Uiso 1 1 calc R . .
C1 C 0.8990(2) 0.60365(17) 0.25303(7) 0.0295(3) Uani 1 1 d . . .
H1 H 0.8700 0.5759 0.3020 0.035 Uiso 1 1 calc R . .
C2 C 0.6984(2) 0.54065(18) 0.19505(7) 0.0311(3) Uani 1 1 d . . .
H2 H 0.5361 0.4697 0.2040 0.037 Uiso 1 1 calc R . .
C3 C 0.7390(2) 0.58307(17) 0.12385(7) 0.0290(3) Uani 1 1 d . . .
H3 H 0.6051 0.5406 0.0830 0.035 Uiso 1 1 calc R . .
C4 C 0.9784(2) 0.68865(16) 0.11294(7) 0.0252(3) Uani 1 1 d . . .
C5 C 1.1685(2) 0.74357(17) 0.17427(7) 0.0274(3) Uani 1 1 d . . .
H5 H 1.3331 0.8143 0.1670 0.033 Uiso 1 1 calc R . .
C6 C 1.0223(2) 0.74026(17) 0.03694(7) 0.0275(3) Uani 1 1 d . . .
C7 C -0.0893(2) 0.14259(16) 0.17048(7) 0.0257(3) Uani 1 1 d . . .
C8 C -0.0899(2) 0.12502(17) 0.25275(7) 0.0278(3) Uani 1 1 d . . .
H8A H -0.1562 -0.0110 0.2548 0.033 Uiso 1 1 calc R . .
H8B H -0.2119 0.1923 0.2749 0.033 Uiso 1 1 calc R . .
C9 C 0.1639(2) 0.20010(17) 0.30329(7) 0.0281(3) Uani 1 1 d . . .
H9A H 0.2301 0.3376 0.3040 0.034 Uiso 1 1 calc R . .
H9B H 0.2893 0.1348 0.2821 0.034 Uiso 1 1 calc R . .
C10 C 0.1331(2) 0.16784(19) 0.38427(7) 0.0313(3) Uani 1 1 d . . .
H10A H 0.0109 0.2366 0.4052 0.038 Uiso 1 1 calc R . .
H10B H 0.0580 0.0308 0.3824 0.038 Uiso 1 1 calc R . .
C11 C 0.3788(2) 0.23131(18) 0.43826(7) 0.0285(3) Uani 1 1 d . . .
H11A H 0.4566 0.3683 0.4408 0.034 Uiso 1 1 calc R . .
H11B H 0.5013 0.1605 0.4191 0.034 Uiso 1 1 calc R . .
C12 C 0.3244(2) 0.19551(19) 0.51739(7) 0.0306(3) Uani 1 1 d . . .
H12A H 0.2000 0.2661 0.5350 0.037 Uiso 1 1 calc R . .
H12B H 0.2419 0.0586 0.5132 0.037 Uiso 1 1 calc R . .
C13 C 0.5502(2) 0.24979(17) 0.57715(7) 0.0267(3) 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 O2 H21 112.6(10) . . ?
C13 O5 H51 110.2(11) . . ?
C1 N1 C5 118.08(11) . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C1 C2 122.86(11) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C3 C2 C1 118.73(12) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 119.13(11) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 117.97(11) . . ?
C5 C4 C6 122.43(11) . . ?
C3 C4 C6 119.60(11) . . ?
N1 C5 C4 123.21(11) . . ?
N1 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
O1 C6 N2 121.72(11) . . ?
O1 C6 C4 119.66(11) . . ?
N2 C6 C4 118.62(11) . . ?
O3 C7 O2 122.83(11) . . ?
O3 C7 C8 122.32(11) . . ?
O2 C7 C8 114.85(10) . . ?
C7 C8 C9 117.13(10) . . ?
C7 C8 H8A 108.0 . . ?
C9 C8 H8A 108.0 . . ?
C7 C8 H8B 108.0 . . ?
C9 C8 H8B 108.0 . . ?
H8A C8 H8B 107.3 . . ?
C8 C9 C10 110.84(10) . . ?
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 . . ?
C11 C10 C9 114.67(10) . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 C12 110.04(10) . . ?
C10 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
C10 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C13 C12 C11 116.28(11) . . ?
C13 C12 H12A 108.2 . . ?
C11 C12 H12A 108.2 . . ?
C13 C12 H12B 108.2 . . ?
C11 C12 H12B 108.2 . . ?
H12A C12 H12B 107.4 . . ?
O4 C13 O5 122.82(12) . . ?
O4 C13 C12 126.14(11) . . ?
O5 C13 C12 111.03(11) . . ?
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 1.2438(15) . ?
O2 C7 1.3110(15) . ?
O2 H21 0.893(18) . ?
O3 C7 1.2213(15) . ?
O4 C13 1.2040(15) . ?
O5 C13 1.3341(15) . ?
O5 H51 0.891(19) . ?
N1 C1 1.3347(16) . ?
N1 C5 1.3385(16) . ?
N2 C6 1.3157(17) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C1 C2 1.3849(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.3844(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3910(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3888(17) . ?
C4 C6 1.4948(17) . ?
C5 H5 0.9500 . ?
C7 C8 1.5023(16) . ?
C8 C9 1.5222(17) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5244(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5176(17) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5222(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.4989(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 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 1.42(18) . . . . ?
N1 C1 C2 C3 -0.87(19) . . . . ?
C1 C2 C3 C4 -0.54(18) . . . . ?
C2 C3 C4 C5 1.31(17) . . . . ?
C2 C3 C4 C6 -178.18(11) . . . . ?
C1 N1 C5 C4 -0.57(18) . . . . ?
C3 C4 C5 N1 -0.79(18) . . . . ?
C6 C4 C5 N1 178.69(11) . . . . ?
C5 C4 C6 O1 176.45(11) . . . . ?
C3 C4 C6 O1 -4.09(18) . . . . ?
C5 C4 C6 N2 -4.11(18) . . . . ?
C3 C4 C6 N2 175.36(12) . . . . ?
O3 C7 C8 C9 170.95(11) . . . . ?
O2 C7 C8 C9 -9.54(16) . . . . ?
C7 C8 C9 C10 -178.65(10) . . . . ?
C8 C9 C10 C11 177.71(10) . . . . ?
C9 C10 C11 C12 179.02(10) . . . . ?
C10 C11 C12 C13 179.52(10) . . . . ?
C11 C12 C13 O4 -2.34(19) . . . . ?
C11 C12 C13 O5 178.20(10) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653540
