#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/95/1559518.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_1559518
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 H19 N4 O3, C8 H5 N4 O5, H2 O'
_chemical_formula_sum            'C22 H26 N8 O9'
_chemical_formula_weight         546.51
_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                91.563(6)
_cell_angle_beta                 100.298(7)
_cell_angle_gamma                107.290(8)
_cell_formula_units_Z            2
_cell_length_a                   8.7029(12)
_cell_length_b                   9.3460(13)
_cell_length_c                   15.910(2)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     1211.2(3)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12781
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.472
_diffrn_reflns_theta_min         2.987
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.119
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       Block
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.472
_exptl_crystal_size_mid          0.365
_exptl_crystal_size_min          0.242
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         5536
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0464
_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)+(0.0499P)²+0.5684P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1153
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4514
_reflns_number_total             5536
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            mp0c00090_si_002.cif
_cod_data_source_block           DM1
_cod_database_code               1559518
_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   0.8653
_shelx_estimated_absorpt_t_max   0.9687
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
O1W O 0.42474(19) 0.0085(2) -0.28196(11) 0.0443(4) Uani 1 1 d . . . . .
C7 C 0.04399(19) 0.29506(18) -0.07683(10) 0.0196(3) Uani 1 1 d . . . . .
H7 H 0.107011 0.365549 -0.107163 0.023 Uiso 1 1 calc R U . . .
O2 O 0.02862(13) 0.20598(12) 0.14643(7) 0.0198(2) Uani 1 1 d . . . . .
N1 N 0.10070(17) 0.41856(16) -0.35884(9) 0.0201(3) Uani 1 1 d . . . . .
N2 N 0.21281(16) 0.21916(15) -0.33907(8) 0.0191(3) Uani 1 1 d . . . . .
O3 O 0.20914(14) 0.41551(13) 0.06268(7) 0.0251(3) Uani 1 1 d . . . . .
N3 N 0.30531(17) 0.39842(16) -0.42928(8) 0.0217(3) Uani 1 1 d . . . . .
H3A H 0.372159 0.352325 -0.440711 0.026 Uiso 1 1 calc R U . . .
H3B H 0.302284 0.479441 -0.452936 0.026 Uiso 1 1 calc R U . . .
O1 O -0.23279(15) -0.00771(13) 0.06524(7) 0.0277(3) Uani 1 1 d . . . . .
C11 C -0.18528(19) 0.07316(18) -0.07528(10) 0.0197(3) Uani 1 1 d . . . . .
H11 H -0.274749 -0.004263 -0.104655 0.024 Uiso 1 1 calc R U . . .
C3 C 0.20616(19) 0.34415(17) -0.37480(9) 0.0178(3) Uani 1 1 d . . . . .
C4 C -0.00867(19) 0.35897(18) -0.30815(10) 0.0200(3) Uani 1 1 d . . . . .
H4 H -0.085154 0.407158 -0.300506 0.024 Uiso 1 1 calc R U . . .
C2 C 0.11222(19) 0.16555(18) -0.28409(10) 0.0194(3) Uani 1 1 d . . . . .
C10 C -0.14706(19) 0.08542(17) 0.01380(10) 0.0191(3) Uani 1 1 d . . . . .
C5 C -0.1396(2) 0.1623(2) -0.21753(10) 0.0223(3) Uani 1 1 d . . . . .
H5A H -0.183563 0.055875 -0.236195 0.027 Uiso 1 1 calc R U . . .
H5B H -0.228532 0.205359 -0.232318 0.027 Uiso 1 1 calc R U . . .
C9 C -0.01206(19) 0.19991(17) 0.05783(9) 0.0173(3) Uani 1 1 d . . . . .
C8 C 0.08198(19) 0.30632(17) 0.01304(10) 0.0182(3) Uani 1 1 d . . . . .
C6 C -0.08845(19) 0.17783(18) -0.12018(10) 0.0182(3) Uani 1 1 d . . . . .
N4 N 0.12894(19) 0.04490(16) -0.24716(9) 0.0271(3) Uani 1 1 d . . . . .
H4A H 0.200888 0.005134 -0.258703 0.033 Uiso 1 1 calc R U . . .
H4B H 0.067892 0.006022 -0.211537 0.033 Uiso 1 1 calc R U . . .
C1 C -0.01074(19) 0.23258(18) -0.26844(10) 0.0192(3) Uani 1 1 d . . . . .
C14 C 0.2839(2) 0.54620(19) 0.02272(11) 0.0267(4) Uani 1 1 d . . . . .
H14A H 0.371166 0.614317 0.063823 0.040 Uiso 1 1 calc R U . . .
H14B H 0.327477 0.517470 -0.024119 0.040 Uiso 1 1 calc R U . . .
H14C H 0.203498 0.594718 0.001599 0.040 Uiso 1 1 calc R U . . .
C12 C -0.3684(2) -0.1335(2) 0.02606(12) 0.0307(4) Uani 1 1 d . . . . .
H12A H -0.416870 -0.188736 0.069698 0.046 Uiso 1 1 calc R U . . .
H12B H -0.448573 -0.098657 -0.009840 0.046 Uiso 1 1 calc R U . . .
H12C H -0.330982 -0.197636 -0.008049 0.046 Uiso 1 1 calc R U . . .
C13 C -0.0498(2) 0.2960(2) 0.18647(11) 0.0301(4) Uani 1 1 d . . . . .
H13A H -0.019310 0.298028 0.247639 0.045 Uiso 1 1 calc R U . . .
H13B H -0.016030 0.396584 0.169419 0.045 Uiso 1 1 calc R U . . .
H13C H -0.166709 0.253850 0.169217 0.045 Uiso 1 1 calc R U . . .
O6 O 0.40701(14) 0.24526(12) 0.29227(7) 0.0208(2) Uani 1 1 d . . . . .
O5 O 0.45161(14) -0.21987(13) 0.41181(7) 0.0235(3) Uani 1 1 d . . . . .
N6 N 0.29413(16) -0.08207(15) 0.45572(8) 0.0190(3) Uani 1 1 d . . . . .
O4 O 0.07867(16) -0.31853(14) 0.58731(8) 0.0301(3) Uani 1 1 d . . . . .
N7 N 0.33673(16) 0.02838(14) 0.40364(8) 0.0183(3) Uani 1 1 d . . . . .
N5 N 0.27794(17) -0.30934(15) 0.50721(9) 0.0209(3) Uani 1 1 d . . . . .
O8 O 0.58201(17) 0.52119(15) 0.16796(8) 0.0356(3) Uani 1 1 d . . . . .
O7 O 0.55925(17) 0.28196(16) 0.16359(9) 0.0372(3) Uani 1 1 d . . . . .
N8 N 0.53165(17) 0.39387(17) 0.19176(9) 0.0255(3) Uani 1 1 d . . . . .
C19 C 0.31750(19) 0.25913(18) 0.35353(10) 0.0195(3) Uani 1 1 d . . . . .
C18 C 0.2740(2) 0.13667(18) 0.40650(10) 0.0194(3) Uani 1 1 d . . . . .
C15 C 0.17370(19) -0.10169(17) 0.50979(10) 0.0193(3) Uani 1 1 d . . . . .
H15A H 0.067445 -0.102981 0.477635 0.023 Uiso 1 1 calc R U . . .
H15B H 0.208726 -0.024569 0.557290 0.023 Uiso 1 1 calc R U . . .
C16 C 0.1718(2) -0.25505(18) 0.53976(10) 0.0211(3) Uani 1 1 d . . . . .
C17 C 0.35167(19) -0.20718(17) 0.45478(10) 0.0187(3) Uani 1 1 d . . . . .
C20 C 0.2914(2) 0.39526(19) 0.35329(10) 0.0225(3) Uani 1 1 d . . . . .
H20 H 0.232753 0.430461 0.388025 0.027 Uiso 1 1 calc R U . . .
C22 C 0.43576(19) 0.37817(18) 0.25610(10) 0.0205(3) Uani 1 1 d . . . . .
C21 C 0.3702(2) 0.47342(19) 0.29023(10) 0.0233(3) Uani 1 1 d . . . . .
H21 H 0.375532 0.570176 0.275559 0.028 Uiso 1 1 calc R U . . .
H18 H 0.202(2) 0.144(2) 0.4447(12) 0.020(4) Uiso 1 1 d . . . . .
H1WA H 0.468(4) -0.064(4) -0.2831(19) 0.078(10) Uiso 1 1 d . . . . .
H1WB H 0.461(4) 0.066(4) -0.320(2) 0.096(12) Uiso 1 1 d . . . . .
H1C H 0.098(3) 0.510(2) -0.3810(13) 0.036(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 0.0000 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
C6 C7 C8 119.49(14) . . ?
C9 O2 C13 111.45(12) . . ?
C4 N1 C3 119.16(14) . . ?
C3 N2 C2 118.47(14) . . ?
C8 O3 C14 117.22(12) . . ?
C10 O1 C12 118.53(13) . . ?
C10 C11 C6 119.45(14) . . ?
N2 C3 N3 119.02(14) . . ?
N2 C3 N1 122.40(14) . . ?
N3 C3 N1 118.58(14) . . ?
C1 C4 N1 122.69(15) . . ?
N4 C2 N2 116.14(14) . . ?
N4 C2 C1 121.59(15) . . ?
N2 C2 C1 122.24(14) . . ?
O1 C10 C9 114.29(14) . . ?
O1 C10 C11 125.34(14) . . ?
C9 C10 C11 120.38(14) . . ?
C1 C5 C6 117.71(13) . . ?
O2 C9 C8 120.43(14) . . ?
O2 C9 C10 119.50(13) . . ?
C8 C9 C10 120.07(14) . . ?
O3 C8 C9 115.17(13) . . ?
O3 C8 C7 124.94(14) . . ?
C9 C8 C7 119.89(14) . . ?
C7 C6 C11 120.68(14) . . ?
C7 C6 C5 122.05(14) . . ?
C11 C6 C5 117.19(14) . . ?
C4 C1 C2 114.74(14) . . ?
C4 C1 C5 122.00(15) . . ?
C2 C1 C5 123.11(14) . . ?
C22 O6 C19 104.60(12) . . ?
N7 N6 C17 121.36(13) . . ?
N7 N6 C15 127.61(13) . . ?
C17 N6 C15 110.58(12) . . ?
C18 N7 N6 117.35(13) . . ?
C16 N5 C17 108.06(13) . . ?
O7 N8 O8 124.61(15) . . ?
O7 N8 C22 118.74(14) . . ?
O8 N8 C22 116.66(15) . . ?
C20 C19 O6 110.23(14) . . ?
C20 C19 C18 131.82(15) . . ?
O6 C19 C18 117.91(14) . . ?
N7 C18 C19 119.80(15) . . ?
N6 C15 C16 99.72(12) . . ?
O4 C16 N5 126.62(15) . . ?
O4 C16 C15 121.50(14) . . ?
N5 C16 C15 111.87(14) . . ?
O5 C17 N5 126.94(15) . . ?
O5 C17 N6 123.31(14) . . ?
N5 C17 N6 109.75(13) . . ?
C19 C20 C21 107.03(14) . . ?
C21 C22 O6 112.87(14) . . ?
C21 C22 N8 131.54(15) . . ?
O6 C22 N8 115.56(14) . . ?
C22 C21 C20 105.25(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
C7 C6 1.389(2) . ?
C7 C8 1.402(2) . ?
O2 C9 1.3859(18) . ?
O2 C13 1.431(2) . ?
N1 C4 1.360(2) . ?
N1 C3 1.358(2) . ?
N2 C3 1.325(2) . ?
N2 C2 1.349(2) . ?
O3 C8 1.3646(19) . ?
O3 C14 1.4274(19) . ?
N3 C3 1.336(2) . ?
O1 C10 1.3621(18) . ?
O1 C12 1.427(2) . ?
C11 C10 1.390(2) . ?
C11 C6 1.393(2) . ?
C4 C1 1.352(2) . ?
C2 N4 1.319(2) . ?
C2 C1 1.444(2) . ?
C10 C9 1.391(2) . ?
C5 C1 1.504(2) . ?
C5 C6 1.524(2) . ?
C9 C8 1.389(2) . ?
O6 C22 1.3575(19) . ?
O6 C19 1.3778(19) . ?
O5 C17 1.2278(19) . ?
N6 N7 1.3486(18) . ?
N6 C17 1.403(2) . ?
N6 C15 1.445(2) . ?
O4 C16 1.241(2) . ?
N7 C18 1.288(2) . ?
N5 C16 1.347(2) . ?
N5 C17 1.375(2) . ?
O8 N8 1.2351(19) . ?
O7 N8 1.2307(19) . ?
N8 C22 1.417(2) . ?
C19 C20 1.357(2) . ?
C19 C18 1.440(2) . ?
C15 C16 1.519(2) . ?
C20 C21 1.414(2) . ?
C22 C21 1.341(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306900
