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#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/95/1559520.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_1559520
loop_
_publ_author_name
'Maity, Dilip Kumar'
'Paul, Rakesh Kumar'
'Desiraju, Gautam R.'
_publ_section_title
;
 Drug-Drug Binary Solids of Nitrofurantoin and Trimethoprim: Crystal
 Engineering and Pharmaceutical Properties.
;
_journal_name_full               'Molecular pharmaceutics'
_journal_paper_doi               10.1021/acs.molpharmaceut.0c00090
_journal_year                    2020
_chemical_formula_moiety         'C14 H18 N4 O3, C8 H6 N4 O5, C3 H7 N O'
_chemical_formula_sum            'C25 H31 N9 O9'
_chemical_formula_weight         601.59
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                101.872(7)
_cell_angle_beta                 94.843(7)
_cell_angle_gamma                110.113(8)
_cell_formula_units_Z            2
_cell_length_a                   8.4865(18)
_cell_length_b                   11.949(3)
_cell_length_c                   15.840(3)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      3.1
_cell_volume                     1454.8(6)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1280
_diffrn_reflns_av_unetI/netI     0.1605
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12662
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.110
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.107
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       Block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.459
_exptl_crystal_size_mid          0.364
_exptl_crystal_size_min          0.264
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         5111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.2297
_refine_ls_R_factor_gt           0.0841
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0837P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1649
_refine_ls_wR_factor_ref         0.2207
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2015
_reflns_number_total             5111
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            mp0c00090_si_002.cif
_cod_data_source_block           DM3
_cod_original_cell_volume        1454.9(5)
_cod_database_code               1559520
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.9109
_shelx_estimated_absorpt_t_max   0.9895
loop_
_space_group_symop_operation_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
O9 O -0.2517(9) 1.5300(6) -0.2365(4) 0.112(2) Uani 1 1 d . . . . .
N9 N -0.1777(12) 1.5758(7) -0.3623(5) 0.111(2) Uani 1 1 d . . . . .
C23 C -0.2648(17) 1.5672(9) -0.2985(9) 0.150(4) Uani 1 1 d . . . . .
H23 H -0.353453 1.595733 -0.303007 0.179 Uiso 1 1 calc R U . . .
C25 C -0.0261(16) 1.5609(11) -0.3517(10) 0.291(11) Uani 1 1 d . . . . .
H25A H 0.063601 1.634193 -0.355575 0.437 Uiso 1 1 calc R U . . .
H25B H -0.029034 1.492346 -0.396643 0.437 Uiso 1 1 calc R U . . .
H25C H -0.005773 1.545627 -0.295372 0.437 Uiso 1 1 calc R U . . .
C24 C -0.2342(18) 1.6030(13) -0.4364(11) 0.293(9) Uani 1 1 d . . . . .
H24A H -0.138556 1.652310 -0.457868 0.439 Uiso 1 1 calc R U . . .
H24B H -0.307513 1.647643 -0.422904 0.439 Uiso 1 1 calc R U . . .
H24C H -0.296095 1.527964 -0.480367 0.439 Uiso 1 1 calc R U . . .
O6 O 0.5449(4) 0.6345(3) 0.1241(2) 0.0478(10) Uani 1 1 d . . . . .
N1 N 0.0869(5) 1.1639(4) -0.0811(3) 0.0426(12) Uani 1 1 d . . . . .
N2 N 0.0511(6) 1.3543(4) -0.0291(3) 0.0473(12) Uani 1 1 d . . . . .
C8 C -0.0581(6) 1.2404(4) -0.1786(3) 0.0383(13) Uani 1 1 d . . . . .
N5 N 0.1930(6) 0.9761(4) -0.0645(3) 0.0475(13) Uani 1 1 d . . . . .
O2 O -0.3923(5) 0.7745(3) -0.5201(2) 0.0545(11) Uani 1 1 d . . . . .
O1 O -0.1964(5) 0.9744(4) -0.5618(2) 0.0644(12) Uani 1 1 d . . . . .
O3 O -0.4839(5) 0.7838(3) -0.3628(2) 0.0618(12) Uani 1 1 d . . . . .
O5 O 0.3126(5) 1.0643(3) 0.0802(2) 0.0563(11) Uani 1 1 d . . . . .
N6 N 0.3147(5) 0.8780(4) 0.0050(3) 0.0459(12) Uani 1 1 d . . . . .
C11 C -0.0296(6) 1.3425(5) -0.1085(3) 0.0405(14) Uani 1 1 d . . . . .
N7 N 0.4010(5) 0.8598(4) 0.0738(3) 0.0454(12) Uani 1 1 d . . . . .
O4 O 0.1188(5) 0.8504(4) -0.2036(2) 0.0682(13) Uani 1 1 d . . . . .
O8 O 0.7405(6) 0.5385(4) 0.2798(3) 0.0915(16) Uani 1 1 d . . . . .
C17 C 0.2745(7) 0.9817(5) 0.0148(4) 0.0440(14) Uani 1 1 d . . . . .
N4 N 0.1896(6) 1.2752(4) 0.0616(3) 0.0621(14) Uani 1 1 d . . . . .
H4A H 0.203541 1.337179 0.104281 0.075 Uiso 1 1 calc R U . . .
H4B H 0.227162 1.219315 0.069728 0.075 Uiso 1 1 calc R U . . .
C7 C -0.1482(7) 1.2312(5) -0.2666(3) 0.0529(16) Uani 1 1 d . . . . .
H7A H -0.072335 1.291900 -0.291794 0.063 Uiso 1 1 calc R U . . .
H7B H -0.246151 1.253747 -0.258080 0.063 Uiso 1 1 calc R U . . .
C22 C 0.6273(7) 0.6380(5) 0.2014(4) 0.0473(14) Uani 1 1 d . . . . .
C4 C -0.3343(7) 0.8852(5) -0.4583(3) 0.0409(14) Uani 1 1 d . . . . .
C9 C 0.0045(6) 1.1561(5) -0.1592(3) 0.0437(14) Uani 1 1 d . . . . .
H9 H -0.011450 1.087313 -0.203981 0.052 Uiso 1 1 calc R U . . .
C2 C -0.1645(7) 1.1004(5) -0.4150(3) 0.0483(15) Uani 1 1 d . . . . .
H2 H -0.089905 1.169899 -0.428126 0.058 Uiso 1 1 calc R U . . .
C3 C -0.2314(7) 0.9893(5) -0.4781(3) 0.0466(15) Uani 1 1 d . . . . .
O7 O 0.6266(6) 0.4477(4) 0.1443(3) 0.0909(16) Uani 1 1 d . . . . .
N3 N -0.0830(6) 1.4331(4) -0.1171(3) 0.0568(13) Uani 1 1 d . . . . .
H3A H -0.064625 1.494289 -0.073000 0.068 Uiso 1 1 calc R U . . .
H3B H -0.135733 1.430364 -0.166771 0.068 Uiso 1 1 calc R U . . .
C5 C -0.3788(7) 0.8931(5) -0.3754(3) 0.0433(14) Uani 1 1 d . . . . .
C1 C -0.2089(7) 1.1078(5) -0.3328(3) 0.0430(14) Uani 1 1 d . . . . .
C19 C 0.5254(7) 0.7436(5) 0.1357(3) 0.0435(14) Uani 1 1 d . . . . .
N8 N 0.6664(7) 0.5337(5) 0.2086(4) 0.0638(15) Uani 1 1 d . . . . .
C10 C 0.1089(7) 1.2657(5) -0.0179(3) 0.0414(13) Uani 1 1 d . . . . .
C18 C 0.4339(7) 0.7617(6) 0.0624(4) 0.0434(14) Uani 1 1 d . . . . .
C6 C -0.3157(7) 1.0039(5) -0.3124(3) 0.0478(15) Uani 1 1 d . . . . .
H6 H -0.344877 1.008454 -0.256882 0.057 Uiso 1 1 calc R U . . .
C16 C 0.1788(7) 0.8750(5) -0.1275(4) 0.0461(15) Uani 1 1 d . . . . .
C21 C 0.6604(7) 0.7429(5) 0.2613(4) 0.0542(16) Uani 1 1 d . . . . .
H21 H 0.717011 0.765289 0.318573 0.065 Uiso 1 1 calc R U . . .
C20 C 0.5918(7) 0.8123(5) 0.2196(4) 0.0558(16) Uani 1 1 d . . . . .
H20 H 0.591523 0.889885 0.244230 0.067 Uiso 1 1 calc R U . . .
C15 C 0.2585(7) 0.8010(5) -0.0838(3) 0.0442(14) Uani 1 1 d . . . . .
H15A H 0.175668 0.720342 -0.085843 0.053 Uiso 1 1 calc R U . . .
H15B H 0.353410 0.791517 -0.110504 0.053 Uiso 1 1 calc R U . . .
C12 C -0.1172(8) 1.0810(5) -0.5902(4) 0.0718(19) Uani 1 1 d . . . . .
H12A H -0.099928 1.058092 -0.649433 0.108 Uiso 1 1 calc R U . . .
H12B H -0.188137 1.128803 -0.587395 0.108 Uiso 1 1 calc R U . . .
H12C H -0.009226 1.128987 -0.553160 0.108 Uiso 1 1 calc R U . . .
C14 C -0.5317(9) 0.7843(6) -0.2782(4) 0.087(2) Uani 1 1 d . . . . .
H14A H -0.604954 0.702768 -0.277862 0.131 Uiso 1 1 calc R U . . .
H14B H -0.431541 0.810755 -0.234890 0.131 Uiso 1 1 calc R U . . .
H14C H -0.590809 0.839695 -0.265231 0.131 Uiso 1 1 calc R U . . .
C13 C -0.5576(9) 0.7427(7) -0.5643(4) 0.100(3) Uani 1 1 d . . . . .
H13A H -0.590873 0.664892 -0.606348 0.150 Uiso 1 1 calc R U . . .
H13B H -0.634752 0.736753 -0.522946 0.150 Uiso 1 1 calc R U . . .
H13C H -0.560529 0.804762 -0.593756 0.150 Uiso 1 1 calc R U . . .
H18 H 0.411(5) 0.705(4) 0.010(3) 0.028(13) Uiso 1 1 d . . . . .
H5 H 0.156(6) 1.031(5) -0.077(3) 0.052(18) 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 0.0000 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
C23 N9 C25 117.6(12) . . ?
C23 N9 C24 121.2(12) . . ?
C25 N9 C24 121.2(13) . . ?
O9 C23 N9 131.6(14) . . ?
C22 O6 C19 105.1(4) . . ?
C9 N1 C10 115.4(4) . . ?
C11 N2 C10 118.0(4) . . ?
C9 C8 C11 114.7(5) . . ?
C9 C8 C7 125.0(4) . . ?
C11 C8 C7 120.3(5) . . ?
C17 N5 C16 113.3(5) . . ?
C4 O2 C13 113.3(4) . . ?
C3 O1 C12 117.7(4) . . ?
C5 O3 C14 117.5(4) . . ?
N7 N6 C17 120.1(4) . . ?
N7 N6 C15 127.9(4) . . ?
C17 N6 C15 112.0(4) . . ?
N3 C11 N2 116.0(4) . . ?
N3 C11 C8 122.0(5) . . ?
N2 C11 C8 122.0(5) . . ?
C18 N7 N6 118.2(4) . . ?
O5 C17 N5 126.9(5) . . ?
O5 C17 N6 126.2(5) . . ?
N5 C17 N6 106.8(5) . . ?
C8 C7 C1 117.2(4) . . ?
C21 C22 O6 112.9(5) . . ?
C21 C22 N8 129.4(6) . . ?
O6 C22 N8 117.7(5) . . ?
C3 C4 O2 120.0(5) . . ?
C3 C4 C5 119.2(5) . . ?
O2 C4 C5 120.8(5) . . ?
N1 C9 C8 125.6(5) . . ?
C1 C2 C3 119.9(5) . . ?
C4 C3 O1 115.7(5) . . ?
C4 C3 C2 120.6(5) . . ?
O1 C3 C2 123.7(5) . . ?
O3 C5 C6 124.9(5) . . ?
O3 C5 C4 114.4(5) . . ?
C6 C5 C4 120.7(5) . . ?
C2 C1 C6 120.1(5) . . ?
C2 C1 C7 119.8(5) . . ?
C6 C1 C7 120.0(5) . . ?
O6 C19 C20 110.2(5) . . ?
O6 C19 C18 116.3(5) . . ?
C20 C19 C18 133.4(5) . . ?
O7 N8 O8 125.1(5) . . ?
O7 N8 C22 118.3(6) . . ?
O8 N8 C22 116.6(6) . . ?
N4 C10 N2 119.0(5) . . ?
N4 C10 N1 116.7(5) . . ?
N2 C10 N1 124.3(5) . . ?
N7 C18 C19 117.7(5) . . ?
C1 C6 C5 119.4(5) . . ?
O4 C16 N5 126.9(5) . . ?
O4 C16 C15 126.4(5) . . ?
N5 C16 C15 106.7(5) . . ?
C22 C21 C20 105.3(5) . . ?
C19 C20 C21 106.5(5) . . ?
N6 C15 C16 101.2(4) . . ?
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
O9 C23 1.170(13) . ?
N9 C23 1.302(12) . ?
N9 C25 1.360(11) . ?
N9 C24 1.372(12) . ?
O6 C22 1.344(6) . ?
O6 C19 1.348(5) . ?
N1 C9 1.337(6) . ?
N1 C10 1.353(6) . ?
N2 C11 1.337(6) . ?
N2 C10 1.346(6) . ?
C8 C9 1.364(6) . ?
C8 C11 1.406(6) . ?
C8 C7 1.496(6) . ?
N5 C17 1.359(6) . ?
N5 C16 1.361(6) . ?
O2 C4 1.374(5) . ?
O2 C13 1.400(6) . ?
O1 C3 1.374(6) . ?
O1 C12 1.405(6) . ?
O3 C5 1.370(6) . ?
O3 C14 1.432(6) . ?
O5 C17 1.206(6) . ?
N6 N7 1.357(5) . ?
N6 C17 1.376(6) . ?
N6 C15 1.452(6) . ?
C11 N3 1.335(6) . ?
N7 C18 1.277(6) . ?
O4 C16 1.202(6) . ?
O8 N8 1.223(6) . ?
N4 C10 1.345(6) . ?
C7 C1 1.513(6) . ?
C22 C21 1.331(7) . ?
C22 N8 1.420(7) . ?
C4 C3 1.366(7) . ?
C4 C5 1.392(7) . ?
C2 C1 1.380(7) . ?
C2 C3 1.387(7) . ?
O7 N8 1.216(6) . ?
C5 C6 1.383(6) . ?
C1 C6 1.381(7) . ?
C19 C20 1.366(7) . ?
C19 C18 1.436(7) . ?
C16 C15 1.518(7) . ?
C21 C20 1.397(7) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306902
