#------------------------------------------------------------------------------
#$Date: 2022-11-10 04:41:11 +0200 (Thu, 10 Nov 2022) $
#$Revision: 279169 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/90/2109091.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_2109091
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_coeditor_code           AW5075
_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 H4 N1 O4  Cl1'
_chemical_formula_sum            'C19 H21 Cl N4 O6'
_chemical_formula_weight         436.85
_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             2021-11-17T09:57:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                103.2150(10)
_cell_angle_beta                 97.7970(10)
_cell_angle_gamma                93.4970(10)
_cell_formula_units_Z            2
_cell_length_a                   7.03810(10)
_cell_length_b                   12.2643(2)
_cell_length_c                   12.4636(2)
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.21
_cell_measurement_theta_min      2.69
_cell_measurement_wavelength     0.71073
_cell_volume                     1032.92(3)
_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 1
_diffrn_measured_fraction_theta_max 0.996
_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  0.0391
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            49833
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.347
_diffrn_reflns_theta_min         1.699
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.516
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.214
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     286
_refine_ls_number_reflns         7362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0518P)²+0.1163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1167
_reflns_Friedel_coverage         0
_reflns_number_gt                4908
_reflns_number_total             7362
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            aw5075sup1.cif
_cod_data_source_block           iz4h4m2p2c4n
_cod_database_code               2109091
_shelx_estimated_absorpt_t_min   0.891
_shelx_estimated_absorpt_t_max   0.953
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 1.03126(19) 0.37903(11) 0.37027(11) 0.0300(3) Uani 1 1 d . . . . .
H1 H 1.107444 0.322189 0.387511 0.036 Uiso 1 1 calc R U . . .
C2 C 1.10327(18) 0.45202(10) 0.31219(10) 0.0274(3) Uani 1 1 d . . . . .
H2 H 1.227246 0.445601 0.290577 0.033 Uiso 1 1 calc R U . . .
C3 C 0.99150(16) 0.53473(9) 0.28602(9) 0.0221(2) Uani 1 1 d . . . . .
C4 C 0.81231(17) 0.54285(10) 0.32108(9) 0.0243(2) Uani 1 1 d . . . . .
H4 H 0.733295 0.59914 0.305471 0.029 Uiso 1 1 calc R U . . .
C5 C 0.75182(17) 0.46681(10) 0.37936(10) 0.0260(2) Uani 1 1 d . . . . .
H5 H 0.629738 0.472445 0.40361 0.031 Uiso 1 1 calc R U . . .
C6 C 1.07473(17) 0.61287(10) 0.22319(9) 0.0242(2) Uani 1 1 d . . . . .
C7 C 0.89322(18) 0.75741(11) 0.03021(11) 0.0323(3) Uani 1 1 d . . . . .
C8 C 0.9548(2) 0.85086(15) -0.02108(17) 0.0562(5) Uani 1 1 d . . . . .
H8A H 1.068284 0.895851 0.026304 0.084 Uiso 1 1 calc R U . . .
H8B H 0.849578 0.898848 -0.027719 0.084 Uiso 1 1 calc R U . . .
H8C H 0.986674 0.818816 -0.095252 0.084 Uiso 1 1 calc R U . . .
C9 C 0.71353(18) 0.68304(10) -0.02818(10) 0.0278(3) Uani 1 1 d . . . . .
H9A H 0.738997 0.603964 -0.031245 0.033 Uiso 1 1 calc R U . . .
H9B H 0.689112 0.69101 -0.106 0.033 Uiso 1 1 calc R U . . .
C10 C 0.52834(17) 0.70466(10) 0.02324(10) 0.0261(2) Uani 1 1 d . . . . .
C11 C 0.3583(2) 0.63429(12) -0.05535(11) 0.0361(3) Uani 1 1 d . . . . .
H11A H 0.386624 0.555551 -0.074828 0.054 Uiso 1 1 calc R U . . .
H11B H 0.335257 0.662082 -0.123259 0.054 Uiso 1 1 calc R U . . .
H11C H 0.243427 0.639809 -0.018681 0.054 Uiso 1 1 calc R U . . .
C12 C 0.4944(2) 0.82883(11) 0.04973(11) 0.0352(3) Uani 1 1 d . . . . .
H12A H 0.379029 0.839181 0.085582 0.053 Uiso 1 1 calc R U . . .
H12B H 0.476347 0.854608 -0.019499 0.053 Uiso 1 1 calc R U . . .
H12C H 0.606045 0.872579 0.100137 0.053 Uiso 1 1 calc R U . . .
C13 C 0.52507(16) 0.15155(9) 0.59221(9) 0.0214(2) Uani 1 1 d . . . . .
C14 C 0.33681(17) 0.11071(10) 0.59639(10) 0.0247(2) Uani 1 1 d . . . . .
C15 C 0.30182(19) 0.02325(10) 0.64708(10) 0.0291(3) Uani 1 1 d . . . . .
H15 H 0.173736 -0.003826 0.650071 0.035 Uiso 1 1 calc R U . . .
C16 C 0.4562(2) -0.02327(10) 0.69279(10) 0.0291(3) Uani 1 1 d . . . . .
C17 C 0.6448(2) 0.01397(11) 0.69107(10) 0.0307(3) Uani 1 1 d . . . . .
H17 H 0.74916 -0.019682 0.723169 0.037 Uiso 1 1 calc R U . . .
C18 C 0.67693(18) 0.10197(10) 0.64105(10) 0.0258(2) Uani 1 1 d . . . . .
H18 H 0.805669 0.129344 0.639906 0.031 Uiso 1 1 calc R U . . .
C19 C 0.57215(16) 0.24531(9) 0.53680(10) 0.0229(2) Uani 1 1 d . . . . .
N1 N 0.85735(15) 0.38605(8) 0.40294(8) 0.0267(2) Uani 1 1 d . . . . .
N2 N 0.94383(16) 0.66115(9) 0.16497(9) 0.0284(2) Uani 1 1 d . . . . .
N3 N 1.00631(15) 0.74647(9) 0.11621(10) 0.0339(3) Uani 1 1 d . . . . .
N4 N 0.4174(2) -0.11651(10) 0.74559(9) 0.0423(3) Uani 1 1 d . . . . .
O1 O 1.24980(12) 0.62644(8) 0.22519(8) 0.0334(2) Uani 1 1 d . . . . .
O2 O 0.55739(14) 0.66816(9) 0.12589(8) 0.0353(2) Uani 1 1 d . . . . .
O3 O 0.74190(12) 0.23927(7) 0.50456(8) 0.0301(2) Uani 1 1 d . . . . .
O4 O 0.46521(13) 0.31639(8) 0.52352(9) 0.0374(2) Uani 1 1 d . . . . .
O5 O 0.5497(2) -0.17307(10) 0.76468(11) 0.0630(3) Uani 1 1 d . . . . .
O6 O 0.25526(19) -0.13293(10) 0.76753(10) 0.0582(3) Uani 1 1 d . . . . .
Cl1 Cl 0.13536(4) 0.16095(3) 0.53595(3) 0.03766(10) Uani 1 1 d . . . . .
H2A H 0.819(2) 0.6508(13) 0.1620(13) 0.042(4) Uiso 1 1 d . . . . .
H2B H 0.459(3) 0.6614(15) 0.1488(15) 0.056(5) Uiso 1 1 d . . . . .
H3A H 0.774(3) 0.2990(19) 0.4693(18) 0.086(7) 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'
Cl Cl 0.1484 0.1585 '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 122.16(11) . . ?
C1 C2 C3 119.07(11) . . ?
C2 C3 C4 118.74(10) . . ?
C2 C3 C6 117.62(10) . . ?
C4 C3 C6 123.62(10) . . ?
C5 C4 C3 118.41(11) . . ?
N1 C5 C4 122.99(11) . . ?
O1 C6 N2 124.72(11) . . ?
O1 C6 C3 120.36(11) . . ?
N2 C6 C3 114.90(10) . . ?
N3 C7 C8 115.82(12) . . ?
N3 C7 C9 127.13(11) . . ?
C8 C7 C9 116.93(12) . . ?
C7 C9 C10 116.85(10) . . ?
O2 C10 C11 109.93(10) . . ?
O2 C10 C12 108.93(10) . . ?
C11 C10 C12 110.91(11) . . ?
O2 C10 C9 105.46(10) . . ?
C11 C10 C9 109.24(10) . . ?
C12 C10 C9 112.23(10) . . ?
C18 C13 C14 117.97(10) . . ?
C18 C13 C19 118.57(10) . . ?
C14 C13 C19 123.46(10) . . ?
C15 C14 C13 121.04(11) . . ?
C15 C14 Cl1 115.90(9) . . ?
C13 C14 Cl1 123.03(9) . . ?
C16 C15 C14 118.65(11) . . ?
C15 C16 C17 122.63(11) . . ?
C15 C16 N4 118.22(12) . . ?
C17 C16 N4 119.15(12) . . ?
C16 C17 C18 117.89(12) . . ?
C17 C18 C13 121.81(11) . . ?
O4 C19 O3 124.55(11) . . ?
O4 C19 C13 123.87(10) . . ?
O3 C19 C13 111.58(9) . . ?
C5 N1 C1 118.60(10) . . ?
C6 N2 N3 119.27(10) . . ?
C7 N3 N2 115.07(10) . . ?
O5 N4 O6 123.97(13) . . ?
O5 N4 C16 117.84(13) . . ?
O6 N4 C16 118.18(13) . . ?
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 1.3429(16) . ?
C1 C2 1.3866(16) . ?
C2 C3 1.3904(16) . ?
C3 C4 1.3916(16) . ?
C3 C6 1.5080(15) . ?
C4 C5 1.3871(16) . ?
C5 N1 1.3352(16) . ?
C6 O1 1.2294(14) . ?
C6 N2 1.3444(16) . ?
C7 N3 1.2836(17) . ?
C7 C8 1.5033(18) . ?
C7 C9 1.5057(19) . ?
C9 C10 1.5398(17) . ?
C10 O2 1.4425(14) . ?
C10 C11 1.5183(18) . ?
C10 C12 1.5235(17) . ?
C13 C18 1.3981(16) . ?
C13 C14 1.3996(16) . ?
C13 C19 1.5125(15) . ?
C14 C15 1.3894(17) . ?
C14 Cl1 1.7281(12) . ?
C15 C16 1.3734(19) . ?
C16 C17 1.3821(18) . ?
C16 N4 1.4729(16) . ?
C17 C18 1.3859(17) . ?
C19 O4 1.2108(14) . ?
C19 O3 1.3121(14) . ?
N2 N3 1.4017(13) . ?
N4 O5 1.2239(18) . ?
N4 O6 1.2249(17) . ?
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
N2 H2A O2 0.874(17) 1.873(17) 2.7074(14) 159.2(15) . yes
O2 H2B O1 0.792(19) 1.935(19) 2.7133(12) 167.3(19) 1_455 yes
O3 H3A N1 0.97(2) 1.62(2) 2.5784(12) 170(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 -0.52(19) . . . . ?
C1 C2 C3 C4 1.28(18) . . . . ?
C1 C2 C3 C6 179.77(11) . . . . ?
C2 C3 C4 C5 -0.91(17) . . . . ?
C6 C3 C4 C5 -179.32(11) . . . . ?
C3 C4 C5 N1 -0.25(18) . . . . ?
C2 C3 C6 O1 -21.78(17) . . . . ?
C4 C3 C6 O1 156.64(12) . . . . ?
C2 C3 C6 N2 156.41(11) . . . . ?
C4 C3 C6 N2 -25.17(16) . . . . ?
N3 C7 C9 C10 81.65(17) . . . . ?
C8 C7 C9 C10 -102.32(14) . . . . ?
C7 C9 C10 O2 -70.15(13) . . . . ?
C7 C9 C10 C11 171.75(11) . . . . ?
C7 C9 C10 C12 48.32(14) . . . . ?
C18 C13 C14 C15 -0.27(17) . . . . ?
C19 C13 C14 C15 179.09(11) . . . . ?
C18 C13 C14 Cl1 -177.98(9) . . . . ?
C19 C13 C14 Cl1 1.38(16) . . . . ?
C13 C14 C15 C16 -0.38(18) . . . . ?
Cl1 C14 C15 C16 177.48(9) . . . . ?
C14 C15 C16 C17 0.48(19) . . . . ?
C14 C15 C16 N4 -179.55(11) . . . . ?
C15 C16 C17 C18 0.10(19) . . . . ?
N4 C16 C17 C18 -179.87(11) . . . . ?
C16 C17 C18 C13 -0.80(18) . . . . ?
C14 C13 C18 C17 0.88(17) . . . . ?
C19 C13 C18 C17 -178.51(11) . . . . ?
C18 C13 C19 O4 -155.92(12) . . . . ?
C14 C13 C19 O4 24.72(18) . . . . ?
C18 C13 C19 O3 24.50(15) . . . . ?
C14 C13 C19 O3 -154.86(11) . . . . ?
C4 C5 N1 C1 1.02(18) . . . . ?
C2 C1 N1 C5 -0.63(18) . . . . ?
O1 C6 N2 N3 -10.50(19) . . . . ?
C3 C6 N2 N3 171.40(10) . . . . ?
C8 C7 N3 N2 178.16(13) . . . . ?
C9 C7 N3 N2 -5.8(2) . . . . ?
C6 N2 N3 C7 153.87(12) . . . . ?
C15 C16 N4 O5 164.78(13) . . . . ?
C17 C16 N4 O5 -15.26(18) . . . . ?
C15 C16 N4 O6 -15.09(17) . . . . ?
C17 C16 N4 O6 164.88(12) . . . . ?

_cod_database_fobs_code 2109091
