#------------------------------------------------------------------------------
#$Date: 2022-11-10 04:41:11 +0200 (Thu, 10 Nov 2022) $
#$Revision: 279169 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/90/2109096.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2109096
loop_
_publ_author_name
'Scheepers, Matthew Clarke'
'Lemmerer, Andreas'
_publ_section_title
;
 Design of a series of cocrystals featuring isoniazid modified with
 diacetone alcohol
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520622009532
_journal_volume                  78
_journal_year                    2022
_chemical_formula_moiety         'C12  H17  N3  O2, C7 H5 N O4'
_chemical_formula_sum            'C19 H22 N4 O6'
_chemical_formula_weight         402.4
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_date             2022-01-06T09:49:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                101.130(2)
_cell_angle_beta                 92.818(2)
_cell_angle_gamma                105.005(2)
_cell_formula_units_Z            2
_cell_length_a                   6.8701(3)
_cell_length_b                   12.1647(6)
_cell_length_c                   12.1779(6)
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.38
_cell_measurement_theta_min      2.72
_cell_measurement_wavelength     0.71073
_cell_volume                     959.26(8)
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            42678
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.528
_diffrn_reflns_theta_min         1.714
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.572
_exptl_crystal_size_mid          0.421
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.052
_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_constraints    0
_refine_ls_number_parameters     277
_refine_ls_number_reflns         5857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.045
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0594P)²+0.2865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.12
_refine_ls_wR_factor_ref         0.1357
_reflns_Friedel_coverage         0
_reflns_number_gt                4742
_reflns_number_total             5857
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            aw5075sup1.cif
_cod_data_source_block           iz4h4m2p4nba
_cod_database_code               2109096
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.989
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1541(2) 0.38928(12) 0.39749(11) 0.0352(3) Uani 1 1 d . . . . .
H1 H -0.258859 0.350927 0.436237 0.042 Uiso 1 1 calc R U . . .
C2 C -0.18684(19) 0.47540(12) 0.34533(11) 0.0330(3) Uani 1 1 d . . . . .
H2 H -0.310744 0.496247 0.34955 0.04 Uiso 1 1 calc R U . . .
C3 C -0.03734(17) 0.53074(11) 0.28704(9) 0.0282(2) Uani 1 1 d . . . . .
C4 C 0.1434(2) 0.49881(13) 0.28520(12) 0.0358(3) Uani 1 1 d . . . . .
H4 H 0.2504 0.535459 0.246799 0.043 Uiso 1 1 calc R U . . .
C5 C 0.1635(2) 0.41250(14) 0.34057(13) 0.0397(3) Uani 1 1 d . . . . .
H5 H 0.286955 0.391043 0.339298 0.048 Uiso 1 1 calc R U . . .
C6 C -0.08285(18) 0.62108(11) 0.22847(10) 0.0284(2) Uani 1 1 d . . . . .
C7 C 0.12358(18) 0.76898(11) 0.02733(11) 0.0311(2) Uani 1 1 d . . . . .
C8 C 0.1066(2) 0.87056(14) -0.02139(16) 0.0459(4) Uani 1 1 d . . . . .
H8A H 0.017029 0.842469 -0.091994 0.069 Uiso 1 1 calc R U . . .
H8B H 0.241178 0.913328 -0.036073 0.069 Uiso 1 1 calc R U . . .
H8C H 0.050525 0.922347 0.032008 0.069 Uiso 1 1 calc R U . . .
C9 C 0.23639(18) 0.68911(10) -0.03456(10) 0.0294(2) Uani 1 1 d . . . . .
H9A H 0.240627 0.700134 -0.112945 0.035 Uiso 1 1 calc R U . . .
H9B H 0.158325 0.60762 -0.03764 0.035 Uiso 1 1 calc R U . . .
C10 C 0.45432(17) 0.70603(10) 0.01601(10) 0.0275(2) Uani 1 1 d . . . . .
C11 C 0.57501(19) 0.83345(11) 0.04678(12) 0.0343(3) Uani 1 1 d . . . . .
H11A H 0.503002 0.877538 0.098032 0.051 Uiso 1 1 calc R U . . .
H11B H 0.591037 0.864717 -0.02162 0.051 Uiso 1 1 calc R U . . .
H11C H 0.708818 0.840248 0.083784 0.051 Uiso 1 1 calc R U . . .
C12 C 0.5590(2) 0.63557(11) -0.06631(11) 0.0351(3) Uani 1 1 d . . . . .
H12A H 0.692034 0.638627 -0.030878 0.053 Uiso 1 1 calc R U . . .
H12B H 0.576211 0.668254 -0.133871 0.053 Uiso 1 1 calc R U . . .
H12C H 0.476164 0.554451 -0.087218 0.053 Uiso 1 1 calc R U . . .
C13 C 0.36829(19) 0.14586(11) 0.58877(10) 0.0310(2) Uani 1 1 d . . . . .
C14 C 0.5757(2) 0.16108(12) 0.60918(11) 0.0353(3) Uani 1 1 d . . . . .
H14 H 0.668564 0.225786 0.590452 0.042 Uiso 1 1 calc R U . . .
C15 C 0.6475(2) 0.08268(13) 0.65652(12) 0.0373(3) Uani 1 1 d . . . . .
H15 H 0.788872 0.092412 0.67056 0.045 Uiso 1 1 calc R U . . .
C16 C 0.5082(2) -0.00987(12) 0.68269(11) 0.0351(3) Uani 1 1 d . . . . .
C17 C 0.3013(2) -0.02690(12) 0.66533(11) 0.0370(3) Uani 1 1 d . . . . .
H17 H 0.209226 -0.091023 0.685514 0.044 Uiso 1 1 calc R U . . .
C18 C 0.2320(2) 0.05244(12) 0.61755(11) 0.0351(3) Uani 1 1 d . . . . .
H18 H 0.090472 0.04278 0.604448 0.042 Uiso 1 1 calc R U . . .
C19 C 0.3010(2) 0.23056(12) 0.53185(11) 0.0336(3) Uani 1 1 d . . . . .
N1 N 0.01815(17) 0.35778(10) 0.39572(10) 0.0360(2) Uani 1 1 d . . . . .
N2 N 0.05309(16) 0.66254(9) 0.16110(9) 0.0297(2) Uani 1 1 d . . . . .
N3 N 0.03172(16) 0.75593(9) 0.11481(10) 0.0326(2) Uani 1 1 d . . . . .
N4 N 0.5837(2) -0.09489(12) 0.73115(11) 0.0451(3) Uani 1 1 d . . . . .
O1 O -0.24155(14) 0.64889(9) 0.24079(8) 0.0372(2) Uani 1 1 d . . . . .
O2 O 0.43284(14) 0.66011(9) 0.11625(8) 0.0346(2) Uani 1 1 d . . . . .
O3 O 0.10264(14) 0.20816(9) 0.51162(9) 0.0385(2) Uani 1 1 d . . . . .
O4 O 0.42121(16) 0.31012(10) 0.50445(10) 0.0479(3) Uani 1 1 d . . . . .
O5 O 0.4607(2) -0.17109(12) 0.76304(12) 0.0632(4) Uani 1 1 d . . . . .
O6 O 0.7659(2) -0.08548(13) 0.73687(14) 0.0671(4) Uani 1 1 d . . . . .
H2A H 0.170(3) 0.6461(14) 0.1561(14) 0.037(4) Uiso 1 1 d . . . . .
H2B H 0.549(3) 0.6666(17) 0.1477(16) 0.052(5) Uiso 1 1 d . . . . .
H3A H 0.079(4) 0.264(2) 0.4718(19) 0.071(6) Uiso 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 0 '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 0.006 '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
N1 C1 C2 122.87(12) . . ?
C3 C2 C1 119.30(12) . . ?
C2 C3 C4 118.22(11) . . ?
C2 C3 C6 117.30(11) . . ?
C4 C3 C6 124.48(11) . . ?
C5 C4 C3 118.50(12) . . ?
N1 C5 C4 123.40(12) . . ?
O1 C6 N2 124.07(11) . . ?
O1 C6 C3 119.82(11) . . ?
N2 C6 C3 116.05(10) . . ?
N3 C7 C8 116.07(12) . . ?
N3 C7 C9 126.61(11) . . ?
C8 C7 C9 117.23(12) . . ?
C7 C9 C10 115.77(10) . . ?
O2 C10 C11 109.36(10) . . ?
O2 C10 C12 109.70(9) . . ?
C11 C10 C12 110.84(10) . . ?
O2 C10 C9 105.04(9) . . ?
C11 C10 C9 112.50(10) . . ?
C12 C10 C9 109.23(10) . . ?
C18 C13 C14 119.96(12) . . ?
C18 C13 C19 122.35(11) . . ?
C14 C13 C19 117.66(12) . . ?
C15 C14 C13 120.50(13) . . ?
C16 C15 C14 118.05(12) . . ?
C15 C16 C17 123.14(12) . . ?
C15 C16 N4 118.32(13) . . ?
C17 C16 N4 118.54(13) . . ?
C16 C17 C18 118.00(13) . . ?
C17 C18 C13 120.34(12) . . ?
O4 C19 O3 123.87(12) . . ?
O4 C19 C13 121.89(12) . . ?
O3 C19 C13 114.21(11) . . ?
C1 N1 C5 117.70(11) . . ?
C6 N2 N3 118.66(10) . . ?
C7 N3 N2 115.47(10) . . ?
O5 N4 O6 123.67(14) . . ?
O5 N4 C16 118.05(14) . . ?
O6 N4 C16 118.28(14) . . ?
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
C1 N1 1.3352(17) . ?
C1 C2 1.3843(18) . ?
C2 C3 1.3821(18) . ?
C3 C4 1.3937(16) . ?
C3 C6 1.5076(16) . ?
C4 C5 1.3839(18) . ?
C5 N1 1.3361(18) . ?
C6 O1 1.2300(14) . ?
C6 N2 1.3383(16) . ?
C7 N3 1.2798(17) . ?
C7 C8 1.4978(17) . ?
C7 C9 1.5091(17) . ?
C9 C10 1.5376(16) . ?
C10 O2 1.4360(14) . ?
C10 C11 1.5200(17) . ?
C10 C12 1.5216(17) . ?
C13 C18 1.3879(19) . ?
C13 C14 1.3916(18) . ?
C13 C19 1.4987(18) . ?
C14 C15 1.3834(19) . ?
C15 C16 1.377(2) . ?
C16 C17 1.382(2) . ?
C16 N4 1.4734(18) . ?
C17 C18 1.3872(19) . ?
C19 O4 1.2115(17) . ?
C19 O3 1.3197(16) . ?
N2 N3 1.3983(14) . ?
N4 O5 1.2204(19) . ?
N4 O6 1.2244(19) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 O4 0.95 2.35 3.2462(17) 156.3 1_455 yes
C4 H4 O2 0.95 2.56 3.4609(16) 159 . yes
C5 H5 O4 0.95 2.63 3.2285(17) 121.4 . yes
C9 H9A O5 0.99 2.63 3.4608(18) 141.2 1_564 yes
C11 H11B O5 0.98 2.64 3.492(2) 144.9 1_564 yes
N2 H2A O2 0.876(17) 1.869(17) 2.6981(14) 157.2(16) . yes
O2 H2B O1 0.84(2) 1.87(2) 2.6884(12) 162.6(19) 1_655 yes
O3 H3A N1 0.94(2) 1.72(2) 2.6646(15) 176(2) . yes
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
N1 C1 C2 C3 1.1(2) . . . . ?
C1 C2 C3 C4 -1.30(19) . . . . ?
C1 C2 C3 C6 178.02(11) . . . . ?
C2 C3 C4 C5 0.7(2) . . . . ?
C6 C3 C4 C5 -178.53(13) . . . . ?
C3 C4 C5 N1 0.1(2) . . . . ?
C2 C3 C6 O1 5.39(17) . . . . ?
C4 C3 C6 O1 -175.34(13) . . . . ?
C2 C3 C6 N2 -171.79(11) . . . . ?
C4 C3 C6 N2 7.49(18) . . . . ?
N3 C7 C9 C10 -81.86(16) . . . . ?
C8 C7 C9 C10 101.78(14) . . . . ?
C7 C9 C10 O2 72.54(12) . . . . ?
C7 C9 C10 C11 -46.33(14) . . . . ?
C7 C9 C10 C12 -169.86(10) . . . . ?
C18 C13 C14 C15 1.0(2) . . . . ?
C19 C13 C14 C15 -176.89(12) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C14 C15 C16 C17 -0.9(2) . . . . ?
C14 C15 C16 N4 178.87(12) . . . . ?
C15 C16 C17 C18 1.1(2) . . . . ?
N4 C16 C17 C18 -178.72(12) . . . . ?
C16 C17 C18 C13 -0.2(2) . . . . ?
C14 C13 C18 C17 -0.8(2) . . . . ?
C19 C13 C18 C17 176.94(12) . . . . ?
C18 C13 C19 O4 -178.07(13) . . . . ?
C14 C13 C19 O4 -0.26(19) . . . . ?
C18 C13 C19 O3 -0.16(18) . . . . ?
C14 C13 C19 O3 177.65(12) . . . . ?
C2 C1 N1 C5 -0.2(2) . . . . ?
C4 C5 N1 C1 -0.4(2) . . . . ?
O1 C6 N2 N3 10.29(18) . . . . ?
C3 C6 N2 N3 -172.67(10) . . . . ?
C8 C7 N3 N2 -178.43(11) . . . . ?
C9 C7 N3 N2 5.17(18) . . . . ?
C6 N2 N3 C7 -159.73(11) . . . . ?
C15 C16 N4 O5 173.89(14) . . . . ?
C17 C16 N4 O5 -6.31(19) . . . . ?
C15 C16 N4 O6 -6.4(2) . . . . ?
C17 C16 N4 O6 173.45(14) . . . . ?

_cod_database_fobs_code 2109096
