#------------------------------------------------------------------------------
#$Date: 2020-11-17 02:44:44 +0200 (Tue, 17 Nov 2020) $
#$Revision: 259155 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/95/1559522.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_1559522
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, C2 H6 O S'
_chemical_formula_sum            'C24 H30 N8 O9 S'
_chemical_formula_weight         606.62
_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                99.371(7)
_cell_angle_beta                 94.665(7)
_cell_angle_gamma                110.431(8)
_cell_formula_units_Z            2
_cell_length_a                   8.792(2)
_cell_length_b                   11.802(3)
_cell_length_c                   15.632(4)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      3.0
_cell_volume                     1482.9(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  0.0382
_diffrn_reflns_av_unetI/netI     0.0455
_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            12245
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.006
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.172
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       Block
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.468
_exptl_crystal_size_mid          0.349
_exptl_crystal_size_min          0.256
_refine_diff_density_max         1.100
_refine_diff_density_min         -0.816
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         5212
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0828
_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)+(0.1175P)²+1.7692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2205
_refine_ls_wR_factor_ref         0.2444
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3610
_reflns_number_total             5212
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            mp0c00090_si_002.cif
_cod_data_source_block           DM5
_cod_original_cell_volume        1482.8(7)
_cod_database_code               1559522
_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   0.9025
_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
O2 O 0.8870(3) 1.2107(2) 0.51716(16) 0.0509(7) Uani 1 1 d . . . . .
O4 O 0.3724(4) 0.1383(3) 0.19775(18) 0.0699(9) Uani 1 1 d . . . . .
N5 N 0.3038(4) 0.0172(3) 0.0592(2) 0.0467(8) Uani 1 1 d D . . . .
N6 N 0.1824(4) 0.1183(3) -0.01101(19) 0.0472(8) Uani 1 1 d . . . . .
N1 N 0.4147(4) 0.8322(3) 0.07905(19) 0.0434(7) Uani 1 1 d . . . . .
N2 N 0.4455(4) 0.6407(3) 0.0297(2) 0.0468(8) Uani 1 1 d . . . . .
N7 N 0.0942(4) 0.1369(3) -0.0793(2) 0.0476(8) Uani 1 1 d . . . . .
O3 O 0.6758(4) 1.0103(3) 0.55704(17) 0.0608(8) Uani 1 1 d . . . . .
O6 O -0.0506(4) 0.3664(2) -0.12796(18) 0.0529(7) Uani 1 1 d . . . . .
O5 O 0.1855(4) -0.0678(3) -0.08518(18) 0.0587(8) Uani 1 1 d . . . . .
N4 N 0.5825(5) 0.5612(3) 0.1183(2) 0.0569(9) Uani 1 1 d . . . . .
H4A H 0.562721 0.499845 0.075388 0.068 Uiso 1 1 calc R U . . .
H4B H 0.636701 0.564150 0.167485 0.068 Uiso 1 1 calc R U . . .
N3 N 0.3057(5) 0.7199(4) -0.0599(2) 0.0682(11) Uani 1 1 d . . . . .
H3A H 0.270271 0.776699 -0.069317 0.082 Uiso 1 1 calc R U . . .
H3B H 0.287194 0.656143 -0.100612 0.082 Uiso 1 1 calc R U . . .
O7 O -0.2562(5) 0.4685(4) -0.2769(3) 0.0981(13) Uani 1 1 d . . . . .
N8 N -0.1756(6) 0.4704(4) -0.2085(3) 0.0741(11) Uani 1 1 d . . . . .
O8 O -0.1273(6) 0.5576(4) -0.1461(3) 0.1042(14) Uani 1 1 d . . . . .
O1 O 0.9947(4) 1.2054(3) 0.36259(18) 0.0612(8) Uani 1 1 d . . . . .
S1 S 0.2625(3) 0.6051(2) -0.30190(15) 0.1386(9) Uani 1 1 d . . . . .
O9A O 0.2121(12) 0.5125(9) -0.2466(8) 0.068(3) Uani 0.5 1 d . . P . .
C23 C 0.4368(12) 0.5881(9) -0.3458(7) 0.161(4) Uani 1 1 d . . . . .
H23A H 0.525827 0.609387 -0.298930 0.242 Uiso 1 1 calc R U . . .
H23B H 0.469199 0.641720 -0.386464 0.242 Uiso 1 1 calc R U . . .
H23C H 0.408810 0.503991 -0.375425 0.242 Uiso 1 1 calc R U . . .
C24 C 0.1224(18) 0.5589(11) -0.3961(7) 0.210(6) Uani 1 1 d . . . . .
H24A H 0.130488 0.487614 -0.432003 0.315 Uiso 1 1 calc R U . . .
H24B H 0.144995 0.624679 -0.427839 0.315 Uiso 1 1 calc R U . . .
H24C H 0.013666 0.538602 -0.381145 0.315 Uiso 1 1 calc R U . . .
O9B O 0.242(3) 0.5232(19) -0.2431(11) 0.176(9) Uani 0.5 1 d . . P . .
C8 C 0.5601(4) 0.7553(3) 0.1776(2) 0.0381(8) Uani 1 1 d . . . . .
C3 C 0.8802(5) 1.0975(3) 0.3733(2) 0.0431(9) Uani 1 1 d . . . . .
C9 C 0.4993(5) 0.8405(3) 0.1577(2) 0.0422(8) Uani 1 1 d . . . . .
H9 H 0.517169 0.909591 0.201173 0.051 Uiso 1 1 calc R U . . .
C4 C 0.8271(5) 1.1019(3) 0.4549(2) 0.0403(8) Uani 1 1 d . . . . .
C11 C 0.5291(5) 0.6522(3) 0.1085(2) 0.0406(8) Uani 1 1 d . . . . .
C7 C 0.6516(5) 0.7613(4) 0.2649(2) 0.0497(10) Uani 1 1 d . . . . .
H7A H 0.748409 0.742519 0.254628 0.060 Uiso 1 1 calc R U . . .
H7B H 0.582376 0.697082 0.291617 0.060 Uiso 1 1 calc R U . . .
C5 C 0.7159(5) 0.9968(4) 0.4737(2) 0.0435(9) Uani 1 1 d . . . . .
C1 C 0.7052(5) 0.8831(3) 0.3298(2) 0.0437(9) Uani 1 1 d . . . . .
C2 C 0.8189(5) 0.9882(4) 0.3109(2) 0.0465(9) Uani 1 1 d . . . . .
H2 H 0.854025 0.985453 0.256314 0.056 Uiso 1 1 calc R U . . .
C6 C 0.6524(5) 0.8878(4) 0.4111(2) 0.0450(9) Uani 1 1 d . . . . .
H6 H 0.574656 0.818072 0.423579 0.054 Uiso 1 1 calc R U . . .
C10 C 0.3900(5) 0.7307(3) 0.0185(2) 0.0433(9) Uani 1 1 d . . . . .
C22 C 0.5887(7) 0.9019(5) 0.5862(3) 0.0735(14) Uani 1 1 d . . . . .
H22A H 0.568296 0.923593 0.644914 0.110 Uiso 1 1 calc R U . . .
H22B H 0.486072 0.857975 0.548208 0.110 Uiso 1 1 calc R U . . .
H22C H 0.652461 0.850309 0.585410 0.110 Uiso 1 1 calc R U . . .
C20 C 1.0575(8) 1.2044(5) 0.2808(3) 0.0916(19) Uani 1 1 d . . . . .
H20A H 1.136461 1.284825 0.280999 0.137 Uiso 1 1 calc R U . . .
H20B H 1.109151 1.144732 0.273001 0.137 Uiso 1 1 calc R U . . .
H20C H 0.968933 1.183027 0.233706 0.137 Uiso 1 1 calc R U . . .
C21 C 1.0379(6) 1.2261(5) 0.5668(3) 0.0741(14) Uani 1 1 d . . . . .
H21A H 1.075659 1.302453 0.609212 0.111 Uiso 1 1 calc R U . . .
H21B H 1.022152 1.158681 0.596476 0.111 Uiso 1 1 calc R U . . .
H21C H 1.118089 1.227717 0.528366 0.111 Uiso 1 1 calc R U . . .
C14 C 0.2211(5) 0.0135(4) -0.0201(2) 0.0449(9) Uani 1 1 d . . . . .
C15 C 0.0625(5) 0.2357(4) -0.0678(3) 0.0491(9) Uani 1 1 d . . . . .
C19 C -0.1386(5) 0.3642(4) -0.2037(3) 0.0522(10) Uani 1 1 d . . . . .
C16 C -0.0302(5) 0.2555(4) -0.1404(3) 0.0482(9) Uani 1 1 d . . . . .
C13 C 0.3141(5) 0.1159(4) 0.1216(3) 0.0472(9) Uani 1 1 d . . . . .
C18 C -0.1747(5) 0.2582(4) -0.2625(3) 0.0586(11) Uani 1 1 d . . . . .
H18 H -0.233542 0.236774 -0.318641 0.070 Uiso 1 1 calc R U . . .
C12 C 0.2369(5) 0.1914(4) 0.0774(2) 0.0490(9) Uani 1 1 d . . . . .
H12A H 0.145327 0.199528 0.105008 0.059 Uiso 1 1 calc R U . . .
H12B H 0.316345 0.272944 0.078046 0.059 Uiso 1 1 calc R U . . .
C17 C -0.1054(5) 0.1869(4) -0.2214(3) 0.0550(10) Uani 1 1 d . . . . .
H17 H -0.109849 0.107981 -0.244929 0.066 Uiso 1 1 calc R U . . .
H15 H 0.095(5) 0.296(4) -0.014(3) 0.045(10) Uiso 1 1 d . . . . .
H H 0.342(6) -0.047(4) 0.065(4) 0.097(18) Uiso 1 1 d 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'
S S 0.1246 0.1234 '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
C4 O2 C21 111.9(3) . . ?
C13 N5 C14 112.7(3) . . ?
N7 N6 C14 119.8(3) . . ?
N7 N6 C12 128.7(3) . . ?
C14 N6 C12 111.4(3) . . ?
C10 N1 C9 115.8(3) . . ?
C10 N2 C11 117.4(3) . . ?
C15 N7 N6 117.4(3) . . ?
C5 O3 C22 117.6(3) . . ?
C19 O6 C16 104.9(3) . . ?
O8 N8 O7 123.8(4) . . ?
O8 N8 C19 119.6(4) . . ?
O7 N8 C19 116.6(5) . . ?
C3 O1 C20 117.1(3) . . ?
O9B S1 O9A 9.6(11) . . ?
O9B S1 C24 117.8(9) . . ?
O9A S1 C24 109.3(6) . . ?
O9B S1 C23 99.2(9) . . ?
O9A S1 C23 106.0(6) . . ?
C24 S1 C23 100.4(6) . . ?
C9 C8 C11 114.9(3) . . ?
C9 C8 C7 125.7(3) . . ?
C11 C8 C7 119.3(3) . . ?
O1 C3 C2 125.0(3) . . ?
O1 C3 C4 115.0(3) . . ?
C2 C3 C4 120.0(3) . . ?
N1 C9 C8 124.8(3) . . ?
C5 C4 O2 120.1(3) . . ?
C5 C4 C3 119.6(3) . . ?
O2 C4 C3 120.2(3) . . ?
N4 C11 N2 116.3(3) . . ?
N4 C11 C8 121.7(3) . . ?
N2 C11 C8 122.0(3) . . ?
C8 C7 C1 116.0(3) . . ?
O3 C5 C4 114.9(3) . . ?
O3 C5 C6 124.5(4) . . ?
C4 C5 C6 120.5(3) . . ?
C6 C1 C2 119.8(3) . . ?
C6 C1 C7 120.2(4) . . ?
C2 C1 C7 119.8(3) . . ?
C3 C2 C1 120.1(3) . . ?
C5 C6 C1 119.9(4) . . ?
N1 C10 N3 117.0(3) . . ?
N1 C10 N2 125.1(3) . . ?
N3 C10 N2 117.9(3) . . ?
O5 C14 N5 126.4(4) . . ?
O5 C14 N6 126.6(4) . . ?
N5 C14 N6 106.9(3) . . ?
N7 C15 C16 117.3(4) . . ?
C18 C19 O6 112.3(3) . . ?
C18 C19 N8 131.3(4) . . ?
O6 C19 N8 116.4(4) . . ?
C17 C16 O6 110.4(3) . . ?
C17 C16 C15 134.1(4) . . ?
O6 C16 C15 115.6(4) . . ?
O4 C13 N5 126.7(4) . . ?
O4 C13 C12 126.4(4) . . ?
N5 C13 C12 106.9(3) . . ?
C19 C18 C17 105.7(4) . . ?
N6 C12 C13 102.0(3) . . ?
C16 C17 C18 106.7(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
O2 C4 1.382(4) . ?
O2 C21 1.419(5) . ?
O4 C13 1.206(5) . ?
N5 C13 1.363(5) . ?
N5 C14 1.371(5) . ?
N6 N7 1.359(4) . ?
N6 C14 1.382(5) . ?
N6 C12 1.448(5) . ?
N1 C10 1.339(5) . ?
N1 C9 1.355(5) . ?
N2 C10 1.343(5) . ?
N2 C11 1.343(5) . ?
N7 C15 1.280(5) . ?
O3 C5 1.376(4) . ?
O3 C22 1.412(5) . ?
O6 C19 1.352(5) . ?
O6 C16 1.367(5) . ?
O5 C14 1.214(5) . ?
N4 C11 1.338(5) . ?
N3 C10 1.342(5) . ?
O7 N8 1.226(6) . ?
N8 O8 1.221(6) . ?
N8 C19 1.411(6) . ?
O1 C3 1.366(5) . ?
O1 C20 1.433(5) . ?
S1 O9B 1.416(17) . ?
S1 O9A 1.473(9) . ?
S1 C24 1.720(10) . ?
S1 C23 1.789(9) . ?
C8 C9 1.357(5) . ?
C8 C11 1.419(5) . ?
C8 C7 1.506(5) . ?
C3 C2 1.387(5) . ?
C3 C4 1.393(5) . ?
C4 C5 1.379(5) . ?
C7 C1 1.514(5) . ?
C5 C6 1.387(5) . ?
C1 C6 1.387(5) . ?
C1 C2 1.389(5) . ?
C15 C16 1.440(6) . ?
C19 C18 1.346(6) . ?
C16 C17 1.361(6) . ?
C13 C12 1.509(6) . ?
C18 C17 1.401(6) . ?
