#------------------------------------------------------------------------------
#$Date: 2025-08-19 11:35:14 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301801 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/14/2021458.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_2021458
loop_
_publ_author_name
'Madeley, Lee G.'
'Levendis, Demetrius C.'
'Lemmerer, Andreas'
_publ_section_title
;
 Covalent-assisted supramolecular synthesis: the effect of hydrogen
 bonding in cocrystals of 4-tert-butylbenzoic acid with isoniazid
 and its derivatized forms
;
_journal_coeditor_code           FA3397
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205322961900055X
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C6 H7 N3 O, C11 H14 O2'
_chemical_formula_moiety         'C6 H7 N3 O, C11 H14 O2'
_chemical_formula_sum            'C17 H21 N3 O3'
_chemical_formula_weight         315.37
_chemical_name_common
;
4-tert-Butylbenzoic acid--isoniazid
;
_chemical_name_systematic
;
4-tert-Butylbenzoic acid--pyridine-4-carbohydrazide (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   mixed
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                94.565(2)
_cell_angle_beta                 93.480(2)
_cell_angle_gamma                94.758(2)
_cell_formula_units_Z            2
_cell_length_a                   6.6076(2)
_cell_length_b                   7.6668(2)
_cell_length_c                   16.5297(5)
_cell_measurement_reflns_used    5430
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.06
_cell_measurement_theta_min      2.48
_cell_volume                     829.94(4)
_computing_cell_refinement
;
SAINT-Plus (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT-Plus and XPREP (Bruker, 2016)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012),
Mercury (Macrae et al.,  2008) and
DIAMOND (Brandenburg, 2006)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13895
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_min         2.478
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.9
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.846
_exptl_crystal_size_mid          0.471
_exptl_crystal_size_min          0.272
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.2
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3992
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0631P)²+0.1039P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1246
_reflns_number_gt                3176
_reflns_number_total             3992
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            fa3397sup1.cif
_cod_data_source_block           I
_cod_database_code               2021458
_cod_database_fobs_code          2021458
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.62281(15) 1.05882(14) 0.41195(7) 0.0344(2) Uani d 1 . .
C C2 0.41780(16) 1.05522(15) 0.38634(8) 0.0407(3) Uani d 1 . .
H H2A 0.34625 1.157015 0.394349 0.049 Uiso calc 1 . .
C C3 0.32042(18) 0.90041(16) 0.34900(8) 0.0452(3) Uani d 1 . .
H H3 0.180262 0.898008 0.331897 0.054 Uiso calc 1 . .
C C4 0.61142(19) 0.75840(15) 0.36048(8) 0.0454(3) Uani d 1 . .
H H4 0.679611 0.655097 0.351111 0.054 Uiso calc 1 . .
C C5 0.71985(17) 0.90663(15) 0.39891(8) 0.0395(3) Uani d 1 . .
H H5 0.859292 0.904382 0.416219 0.047 Uiso calc 1 . .
C C6 0.74764(15) 1.21634(14) 0.45485(7) 0.0354(2) Uani d 1 . .
N N1 0.64879(14) 1.35761(12) 0.47241(7) 0.0396(2) Uani d 1 . .
N N2 0.41444(16) 0.75400(13) 0.33587(7) 0.0460(3) Uani d 1 . .
N N3 0.74431(14) 1.50755(13) 0.51959(8) 0.0434(3) Uani d 1 . .
O O1 0.92956(11) 1.21112(10) 0.47285(6) 0.0478(2) Uani d 1 . .
H H1 0.522(2) 1.3601(19) 0.4640(9) 0.056(4) Uiso d 1 . .
H H3A 0.832(2) 1.5626(19) 0.4890(9) 0.053(4) Uiso d 1 . .
H H3B 0.818(3) 1.469(2) 0.5638(10) 0.064(5) Uiso d 1 . .
C C7 -0.01943(19) 0.24213(15) 0.22933(8) 0.0435(3) Uani d 1 . .
C C8 0.1039(2) 0.13611(19) 0.18693(10) 0.0599(4) Uani d 1 . .
H H8 0.245581 0.169776 0.186951 0.072 Uiso calc 1 . .
C C9 0.0218(2) -0.01964(19) 0.14422(10) 0.0630(4) Uani d 1 . .
H H9 0.109123 -0.091708 0.115837 0.076 Uiso calc 1 . .
C C10 -0.1842(2) -0.07236(16) 0.14201(8) 0.0468(3) Uani d 1 . .
C C11 -0.3059(2) 0.03606(17) 0.18471(8) 0.0497(3) Uani d 1 . .
H H11 -0.447876 0.003577 0.184148 0.06 Uiso calc 1 . .
C C12 -0.2251(2) 0.19077(16) 0.22821(8) 0.0468(3) Uani d 1 . .
H H12 -0.311667 0.261965 0.257455 0.056 Uiso calc 1 . .
C C13 0.06626(19) 0.40888(16) 0.27600(8) 0.0454(3) Uani d 1 . .
C C14 -0.2730(2) -0.24347(17) 0.09333(8) 0.0508(3) Uani d 1 . .
C C15A -0.1006(5) -0.3523(4) 0.0598(3) 0.0816(12) Uani d 0.512(3) A 1
H H15A -0.011286 -0.381706 0.105315 0.122 Uiso calc 0.512(3) A 1
H H15B -0.161859 -0.460726 0.029345 0.122 Uiso calc 0.512(3) A 1
H H15C -0.020901 -0.282587 0.023727 0.122 Uiso calc 0.512(3) A 1
C C16A -0.3861(6) -0.3610(4) 0.15009(18) 0.0671(10) Uani d 0.512(3) A 1
H H16A -0.29118 -0.387776 0.194336 0.101 Uiso calc 0.512(3) A 1
H H16B -0.496856 -0.299671 0.172867 0.101 Uiso calc 0.512(3) A 1
H H16C -0.442549 -0.470515 0.119273 0.101 Uiso calc 0.512(3) A 1
C C17A -0.4086(6) -0.1984(4) 0.02516(18) 0.0691(10) Uani d 0.512(3) A 1
H H17A -0.466598 -0.306415 -0.006533 0.104 Uiso calc 0.512(3) A 1
H H17B -0.518719 -0.134268 0.04666 0.104 Uiso calc 0.512(3) A 1
H H17C -0.330555 -0.124771 -0.009868 0.104 Uiso calc 0.512(3) A 1
C C15B -0.5132(4) -0.2689(4) 0.0931(2) 0.0628(9) Uani d 0.488(3) A 2
H H15D -0.571654 -0.169519 0.069453 0.094 Uiso calc 0.488(3) A 2
H H15E -0.56346 -0.378158 0.060649 0.094 Uiso calc 0.488(3) A 2
H H15F -0.553085 -0.274749 0.149011 0.094 Uiso calc 0.488(3) A 2
C C16B -0.2278(6) -0.2352(4) 0.00347(17) 0.0638(9) Uani d 0.488(3) A 2
H H16D -0.285525 -0.132756 -0.01759 0.096 Uiso calc 0.488(3) A 2
H H16E -0.080273 -0.225248 -0.001203 0.096 Uiso calc 0.488(3) A 2
H H16F -0.288967 -0.342319 -0.028049 0.096 Uiso calc 0.488(3) A 2
C C17B -0.1904(6) -0.3950(4) 0.1292(2) 0.0640(10) Uani d 0.488(3) A 2
H H17D -0.247378 -0.50385 0.097985 0.096 Uiso calc 0.488(3) A 2
H H17E -0.041834 -0.384827 0.127741 0.096 Uiso calc 0.488(3) A 2
H H17F -0.226979 -0.396977 0.18571 0.096 Uiso calc 0.488(3) A 2
O O2 0.25825(15) 0.45139(13) 0.26351(7) 0.0629(3) Uani d 1 . .
O O3 -0.03104(14) 0.49683(12) 0.32126(6) 0.0536(3) Uani d 1 . .
H H2 0.305(3) 0.566(3) 0.2930(13) 0.105(7) Uiso d 1 . .
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -2 0.347
0 0 -1 0.136
0 0 1 0.027
1 -2 1 0.154
-1 2 -1 0.228
2 0 -1 0.267
-2 0 1 0.273
1 -1 0 0.127
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 C1 C2 118.35(10)
C5 C1 C6 117.00(9)
C2 C1 C6 124.63(9)
C3 C2 C1 118.63(10)
C3 C2 H2A 120.7
C1 C2 H2A 120.7
N2 C3 C2 123.01(11)
N2 C3 H3 118.5
C2 C3 H3 118.5
N2 C4 C5 122.77(11)
N2 C4 H4 118.6
C5 C4 H4 118.6
C4 C5 C1 119.16(10)
C4 C5 H5 120.4
C1 C5 H5 120.4
O1 C6 N1 122.89(10)
O1 C6 C1 120.74(9)
N1 C6 C1 116.36(9)
C6 N1 N3 121.69(9)
C6 N1 H1 123.8(10)
N3 N1 H1 113.7(10)
C3 N2 C4 118.07(10)
N1 N3 H3A 108.0(9)
N1 N3 H3B 108.0(10)
H3A N3 H3B 108.4(14)
C8 C7 C12 118.83(11)
C8 C7 C13 121.01(11)
C12 C7 C13 120.16(11)
C7 C8 C9 120.28(13)
C7 C8 H8 119.9
C9 C8 H8 119.9
C10 C9 C8 121.59(13)
C10 C9 H9 119.2
C8 C9 H9 119.2
C9 C10 C11 117.33(11)
C9 C10 C14 120.93(12)
C11 C10 C14 121.75(12)
C12 C11 C10 121.51(12)
C12 C11 H11 119.2
C10 C11 H11 119.2
C7 C12 C11 120.45(12)
C7 C12 H12 119.8
C11 C12 H12 119.8
O3 C13 O2 123.28(11)
O3 C13 C7 123.46(11)
O2 C13 C7 113.27(11)
C17B C14 C10 109.72(16)
C17A C14 C10 108.49(15)
C17A C14 C16A 112.0(2)
C10 C14 C16A 109.24(14)
C17B C14 C16B 112.5(2)
C10 C14 C16B 109.36(15)
C17A C14 C15A 109.9(2)
C10 C14 C15A 111.41(15)
C16A C14 C15A 105.7(2)
C17B C14 C15B 108.0(2)
C10 C14 C15B 112.18(14)
C16B C14 C15B 105.1(2)
C14 C15A H15A 109.5
C14 C15A H15B 109.5
H15A C15A H15B 109.5
C14 C15A H15C 109.5
H15A C15A H15C 109.5
H15B C15A H15C 109.5
C14 C16A H16A 109.5
C14 C16A H16B 109.5
H16A C16A H16B 109.5
C14 C16A H16C 109.5
H16A C16A H16C 109.5
H16B C16A H16C 109.5
C14 C17A H17A 109.5
C14 C17A H17B 109.5
H17A C17A H17B 109.5
C14 C17A H17C 109.5
H17A C17A H17C 109.5
H17B C17A H17C 109.5
C14 C15B H15D 109.5
C14 C15B H15E 109.5
H15D C15B H15E 109.5
C14 C15B H15F 109.5
H15D C15B H15F 109.5
H15E C15B H15F 109.5
C14 C16B H16D 109.5
C14 C16B H16E 109.5
H16D C16B H16E 109.5
C14 C16B H16F 109.5
H16D C16B H16F 109.5
H16E C16B H16F 109.5
C14 C17B H17D 109.5
C14 C17B H17E 109.5
H17D C17B H17E 109.5
C14 C17B H17F 109.5
H17D C17B H17F 109.5
H17E C17B H17F 109.5
C13 O2 H2 110.1(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C5 1.3857(15)
C1 C2 1.3918(15)
C1 C6 1.5063(15)
C2 C3 1.3828(16)
C2 H2A 0.95
C3 N2 1.3365(16)
C3 H3 0.95
C4 N2 1.3367(16)
C4 C5 1.3795(16)
C4 H4 0.95
C5 H5 0.95
C6 O1 1.2254(12)
C6 N1 1.3321(14)
N1 N3 1.4161(13)
N1 H1 0.844(16)
N3 H3A 0.892(16)
N3 H3B 0.934(17)
C7 C8 1.3802(18)
C7 C12 1.3815(17)
C7 C13 1.4900(16)
C8 C9 1.3895(19)
C8 H8 0.95
C9 C10 1.385(2)
C9 H9 0.95
C10 C11 1.3864(18)
C10 C14 1.5363(17)
C11 C12 1.3862(17)
C11 H11 0.95
C12 H12 0.95
C13 O3 1.2157(15)
C13 O2 1.3161(16)
C14 C17B 1.475(3)
C14 C17A 1.477(3)
C14 C16A 1.536(3)
C14 C16B 1.538(3)
C14 C15A 1.569(3)
C14 C15B 1.582(3)
C15A H15A 0.98
C15A H15B 0.98
C15A H15C 0.98
C16A H16A 0.98
C16A H16B 0.98
C16A H16C 0.98
C17A H17A 0.98
C17A H17B 0.98
C17A H17C 0.98
C15B H15D 0.98
C15B H15E 0.98
C15B H15F 0.98
C16B H16D 0.98
C16B H16E 0.98
C16B H16F 0.98
C17B H17D 0.98
C17B H17E 0.98
C17B H17F 0.98
O2 H2 0.98(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 N3 2_686 0.844(16) 2.122(15) 2.8807(13) 149.0(10) yes
N3 H3A O1 2_786 0.892(16) 2.269(16) 2.9095(13) 129.0(10) yes
N3 H3B O3 2_676 0.934(17) 2.279(17) 3.1513(15) 155.0(10) yes
O2 H2 N2 . 0.98(2) 1.65(2) 2.6248(13) 172(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
C5 C1 C2 C3 -0.10(18)
C6 C1 C2 C3 -178.74(11)
C1 C2 C3 N2 -0.4(2)
N2 C4 C5 C1 -0.9(2)
C2 C1 C5 C4 0.71(18)
C6 C1 C5 C4 179.45(11)
C5 C1 C6 O1 4.05(17)
C2 C1 C6 O1 -177.29(12)
C5 C1 C6 N1 -175.15(11)
C2 C1 C6 N1 3.51(17)
O1 C6 N1 N3 -5.51(18)
C1 C6 N1 N3 173.67(10)
C2 C3 N2 C4 0.30(19)
C5 C4 N2 C3 0.3(2)
C12 C7 C8 C9 -0.2(2)
C13 C7 C8 C9 179.51(14)
C7 C8 C9 C10 0.7(3)
C8 C9 C10 C11 -0.4(2)
C8 C9 C10 C14 178.98(14)
C9 C10 C11 C12 -0.3(2)
C14 C10 C11 C12 -179.67(12)
C8 C7 C12 C11 -0.5(2)
C13 C7 C12 C11 179.80(12)
C10 C11 C12 C7 0.7(2)
C8 C7 C13 O3 -171.73(14)
C12 C7 C13 O3 8.0(2)
C8 C7 C13 O2 8.11(19)
C12 C7 C13 O2 -172.18(12)
C9 C10 C14 C17B 65.0(2)
C11 C10 C14 C17B -115.6(2)
C9 C10 C14 C17A -113.6(2)
C11 C10 C14 C17A 65.8(2)
C9 C10 C14 C16A 124.0(2)
C11 C10 C14 C16A -56.6(2)
C9 C10 C14 C16B -58.8(2)
C11 C10 C14 C16B 120.6(2)
C9 C10 C14 C15A 7.6(3)
C11 C10 C14 C15A -173.0(2)
C9 C10 C14 C15B -174.96(18)
C11 C10 C14 C15B 4.4(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139062877
