#------------------------------------------------------------------------------
#$Date: 2023-03-04 19:09:31 +0100 (Sat 04 de Mar de 2023) $
#$Revision: 281412 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/61/7246192.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_7246192
loop_
_publ_author_name
'Surampudi, Anuja Venkata Sai Durga'
'Ramakrishna, Sistla'
'Pallavi, Alegete'
'Balasubramanian, Sridhar'
_publ_section_title
;
 Novel salts and cocrystals of the antifolate drug trimethoprim and their
 role in the enhancement of solubility and dissolution
;
_journal_issue                   8
_journal_name_full               CrystEngComm
_journal_page_first              1220
_journal_page_last               1231
_journal_paper_doi               10.1039/D2CE01436J
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C20 H24 N4 O5'
_chemical_formula_sum            'C20 H24 N4 O5'
_chemical_formula_weight         400.43
_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-2018/3
_audit_update_record
;
2022-06-20 deposited with the CCDC.	2023-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                108.0068(18)
_cell_angle_beta                 111.5684(18)
_cell_angle_gamma                99.678(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0355(6)
_cell_length_b                   10.9956(7)
_cell_length_c                   11.9267(7)
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      30.0615
_cell_measurement_theta_min      2.4445
_cell_volume                     993.38(11)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            32063
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.569
_diffrn_reflns_theta_min         2.444
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            BROWN
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.039
_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     289
_refine_ls_number_reflns         6041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0492
_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)+(0.0551P)²+0.2680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1476
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3997
_reflns_number_total             6041
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01436j2.cif
_cod_data_source_block           KA111_0m
_cod_depositor_comments
'Adding full bibliography for 7246190--7246193.cif.'
_cod_database_code               7246192
_shelx_shelxl_version_number     2018/3
_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   0.974
_shelx_estimated_absorpt_t_max   0.985
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
C1 C 0.54500(16) 0.40324(12) 0.82941(12) 0.0347(3) Uani 1 1 d . . . . .
C2 C 0.72241(17) 0.44236(13) 0.89405(12) 0.0355(3) Uani 1 1 d . . . . .
C3 C 0.73629(17) 0.66279(12) 0.99032(13) 0.0355(3) Uani 1 1 d . . . . .
C4 C 0.48003(17) 0.50657(14) 0.85148(13) 0.0406(3) Uani 1 1 d . . . . .
H4 H 0.363864 0.485007 0.809851 0.049 Uiso 1 1 calc R U . . .
C5 C 0.43561(18) 0.25859(13) 0.75346(13) 0.0416(3) Uani 1 1 d . . . . .
H5A H 0.326883 0.253688 0.752406 0.050 Uiso 1 1 calc R U . . .
H5B H 0.484055 0.207498 0.802076 0.050 Uiso 1 1 calc R U . . .
C6 C 0.40642(16) 0.18795(12) 0.61239(12) 0.0353(3) Uani 1 1 d . . . . .
C7 C 0.48530(18) 0.24734(14) 0.55381(13) 0.0405(3) Uani 1 1 d . . . . .
H7 H 0.557947 0.335546 0.600542 0.049 Uiso 1 1 calc R U . . .
C8 C 0.45579(18) 0.17465(14) 0.42408(14) 0.0419(3) Uani 1 1 d . . . . .
C9 C 0.34382(19) 0.04438(14) 0.35282(13) 0.0426(3) Uani 1 1 d . . . . .
C10 C 0.26330(17) -0.01376(13) 0.41194(13) 0.0401(3) Uani 1 1 d . . . . .
C11 C 0.29556(17) 0.05634(13) 0.54138(13) 0.0390(3) Uani 1 1 d . . . . .
H11 H 0.243409 0.015737 0.580829 0.047 Uiso 1 1 calc R U . . .
C12 C 0.6145(3) 0.3605(2) 0.4098(2) 0.0778(6) Uani 1 1 d . . . . .
H12A H 0.659374 0.378645 0.352952 0.117 Uiso 1 1 calc R U . . .
H12B H 0.704039 0.390592 0.496808 0.117 Uiso 1 1 calc R U . . .
H12C H 0.534819 0.407594 0.413191 0.117 Uiso 1 1 calc R U . . .
C13 C 0.2317(2) 0.0136(2) 0.12826(16) 0.0606(5) Uani 1 1 d . . . . .
H13A H 0.180871 -0.059505 0.042755 0.091 Uiso 1 1 calc R U . . .
H13B H 0.312058 0.085189 0.131054 0.091 Uiso 1 1 calc R U . . .
H13C H 0.146676 0.046229 0.145094 0.091 Uiso 1 1 calc R U . . .
C14 C 0.0733(3) -0.20820(18) 0.3904(2) 0.0669(5) Uani 1 1 d . . . . .
H14A H 0.008028 -0.299321 0.328288 0.100 Uiso 1 1 calc R U . . .
H14B H 0.001070 -0.161404 0.413124 0.100 Uiso 1 1 calc R U . . .
H14C H 0.156634 -0.208742 0.468330 0.100 Uiso 1 1 calc R U . . .
N1 N 0.81637(14) 0.57100(11) 0.97636(11) 0.0389(3) Uani 1 1 d . . . . .
N2 N 0.57039(15) 0.63766(11) 0.92879(12) 0.0407(3) Uani 1 1 d . . . . .
N3 N 0.80434(18) 0.35301(13) 0.87731(14) 0.0521(4) Uani 1 1 d . . . . .
H1N H 0.916(3) 0.3801(19) 0.9255(19) 0.057(5) Uiso 1 1 d . . . . .
H2N H 0.747(2) 0.267(2) 0.8267(19) 0.062(5) Uiso 1 1 d . . . . .
N4 N 0.83243(19) 0.79138(12) 1.07332(14) 0.0513(3) Uani 1 1 d . . . . .
H3N H 0.943(3) 0.8093(19) 1.1258(19) 0.060(5) Uiso 1 1 d . . . . .
H4N H 0.786(2) 0.8526(19) 1.0948(18) 0.056(5) Uiso 1 1 d . . . . .
O1 O 0.53504(17) 0.22219(12) 0.36095(12) 0.0626(3) Uani 1 1 d . . . . .
O2 O 0.31452(17) -0.03280(12) 0.22631(10) 0.0599(3) Uani 1 1 d . . . . .
O3 O 0.15339(14) -0.14199(10) 0.33334(11) 0.0549(3) Uani 1 1 d . . . . .
C15 C 0.25801(18) 0.78267(14) 0.85046(14) 0.0412(3) Uani 1 1 d . . . . .
C16 C 0.1947(2) 0.86301(15) 0.78737(15) 0.0450(3) Uani 1 1 d . . . . .
C17 C 0.0270(2) 0.82156(19) 0.70112(19) 0.0641(5) Uani 1 1 d . . . . .
H17 H -0.014856 0.875015 0.658504 0.077 Uiso 1 1 calc R U . . .
C18 C -0.0791(3) 0.7010(2) 0.6777(3) 0.0869(7) Uani 1 1 d . . . . .
H18 H -0.192205 0.672823 0.618721 0.104 Uiso 1 1 calc R U . . .
C19 C -0.0176(3) 0.6226(2) 0.7415(3) 0.0803(7) Uani 1 1 d . . . . .
H19 H -0.089583 0.542056 0.726878 0.096 Uiso 1 1 calc R U . . .
C20 C 0.1507(2) 0.66310(17) 0.82740(18) 0.0544(4) Uani 1 1 d . . . . .
H20 H 0.191799 0.609352 0.869900 0.065 Uiso 1 1 calc R U . . .
O4 O 0.42420(14) 0.83140(11) 0.93637(12) 0.0575(3) Uani 1 1 d . . . . .
H4O H 0.471(3) 0.760(2) 0.938(2) 0.082(7) Uiso 1 1 d . . . . .
O5 O 0.29666(18) 0.98442(12) 0.81252(15) 0.0635(4) Uani 1 1 d . . . . .
H5O H 0.400(4) 0.997(3) 0.873(3) 0.111(10) 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
C4 C1 C2 114.74(12) . . ?
C4 C1 C5 122.08(13) . . ?
C2 C1 C5 122.91(12) . . ?
N3 C2 N1 116.87(12) . . ?
N3 C2 C1 121.56(12) . . ?
N1 C2 C1 121.57(11) . . ?
N2 C3 N1 125.58(12) . . ?
N2 C3 N4 117.63(12) . . ?
N1 C3 N4 116.78(12) . . ?
N2 C4 C1 125.40(13) . . ?
N2 C4 H4 117.3 . . ?
C1 C4 H4 117.3 . . ?
C1 C5 C6 118.25(12) . . ?
C1 C5 H5A 107.7 . . ?
C6 C5 H5A 107.7 . . ?
C1 C5 H5B 107.7 . . ?
C6 C5 H5B 107.7 . . ?
H5A C5 H5B 107.1 . . ?
C7 C6 C11 119.86(12) . . ?
C7 C6 C5 123.14(11) . . ?
C11 C6 C5 116.99(13) . . ?
C6 C7 C8 120.04(13) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
O1 C8 C9 115.78(12) . . ?
O1 C8 C7 124.09(13) . . ?
C9 C8 C7 120.11(14) . . ?
O2 C9 C8 122.26(15) . . ?
O2 C9 C10 118.26(13) . . ?
C8 C9 C10 119.41(12) . . ?
O3 C10 C11 124.11(14) . . ?
O3 C10 C9 115.21(12) . . ?
C11 C10 C9 120.69(12) . . ?
C10 C11 C6 119.86(14) . . ?
C10 C11 H11 120.1 . . ?
C6 C11 H11 120.1 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 N1 C2 117.54(11) . . ?
C3 N2 C4 115.01(11) . . ?
C2 N3 H1N 119.0(12) . . ?
C2 N3 H2N 119.9(13) . . ?
H1N N3 H2N 120.7(18) . . ?
C3 N4 H3N 119.3(12) . . ?
C3 N4 H4N 120.2(12) . . ?
H3N N4 H4N 117.9(17) . . ?
C8 O1 C12 119.20(13) . . ?
C9 O2 C13 115.47(12) . . ?
C10 O3 C14 117.56(12) . . ?
O4 C15 C20 123.88(14) . . ?
O4 C15 C16 116.76(14) . . ?
C20 C15 C16 119.31(14) . . ?
O5 C16 C17 119.39(14) . . ?
O5 C16 C15 120.55(14) . . ?
C17 C16 C15 120.04(16) . . ?
C16 C17 C18 120.20(17) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 119.91(19) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.17(19) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 120.35(17) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C15 O4 H4O 111.1(14) . . ?
C16 O5 H5O 107.5(18) . . ?
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 C4 1.3630(18) . ?
C1 C2 1.4154(18) . ?
C1 C5 1.4999(17) . ?
C2 N3 1.3361(17) . ?
C2 N1 1.3454(16) . ?
C3 N2 1.3373(17) . ?
C3 N1 1.3417(16) . ?
C3 N4 1.3503(17) . ?
C4 N2 1.3504(17) . ?
C4 H4 0.9300 . ?
C5 C6 1.5168(18) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.384(2) . ?
C6 C11 1.3950(18) . ?
C7 C8 1.4016(19) . ?
C7 H7 0.9300 . ?
C8 O1 1.3663(19) . ?
C8 C9 1.388(2) . ?
C9 O2 1.3806(16) . ?
C9 C10 1.391(2) . ?
C10 O3 1.3713(16) . ?
C10 C11 1.3857(19) . ?
C11 H11 0.9300 . ?
C12 O1 1.395(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O2 1.429(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O3 1.417(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N3 H1N 0.90(2) . ?
N3 H2N 0.89(2) . ?
N4 H3N 0.91(2) . ?
N4 H4N 0.87(2) . ?
C15 O4 1.3604(18) . ?
C15 C20 1.377(2) . ?
C15 C16 1.392(2) . ?
C16 O5 1.363(2) . ?
C16 C17 1.376(2) . ?
C17 C18 1.379(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.380(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
O4 H4O 0.95(2) . ?
O5 H5O 0.90(3) . ?
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
N3 H1N N1 0.90(2) 2.14(2) 3.0376(18) 174.1(17) 2_767 yes
N3 H2N O2 0.89(2) 2.36(2) 3.1843(18) 154.7(17) 2_656 yes
N3 H2N O3 0.89(2) 2.526(19) 3.0398(17) 117.6(15) 2_656 yes
N4 H3N O3 0.91(2) 2.32(2) 3.1357(19) 148.2(16) 1_666 yes
N4 H4N O5 0.87(2) 2.19(2) 3.0579(19) 169.0(17) 2_677 yes
O4 H4O N2 0.95(2) 1.74(2) 2.6844(15) 172(2) . yes
O5 H5O O4 0.90(3) 2.19(3) 2.6977(17) 115(2) . yes
O5 H5O O4 0.90(3) 2.22(3) 2.9002(19) 132(2) 2_677 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
C4 C1 C2 N3 -177.12(14) . . . . ?
C5 C1 C2 N3 8.7(2) . . . . ?
C4 C1 C2 N1 3.6(2) . . . . ?
C5 C1 C2 N1 -170.58(13) . . . . ?
C2 C1 C4 N2 -0.7(2) . . . . ?
C5 C1 C4 N2 173.53(13) . . . . ?
C4 C1 C5 C6 103.51(16) . . . . ?
C2 C1 C5 C6 -82.71(17) . . . . ?
C1 C5 C6 C7 4.8(2) . . . . ?
C1 C5 C6 C11 -175.95(12) . . . . ?
C11 C6 C7 C8 -1.0(2) . . . . ?
C5 C6 C7 C8 178.24(13) . . . . ?
C6 C7 C8 O1 -176.16(14) . . . . ?
C6 C7 C8 C9 1.8(2) . . . . ?
O1 C8 C9 O2 0.2(2) . . . . ?
C7 C8 C9 O2 -177.91(13) . . . . ?
O1 C8 C9 C10 177.25(13) . . . . ?
C7 C8 C9 C10 -0.9(2) . . . . ?
O2 C9 C10 O3 -3.70(19) . . . . ?
C8 C9 C10 O3 179.18(12) . . . . ?
O2 C9 C10 C11 176.25(12) . . . . ?
C8 C9 C10 C11 -0.9(2) . . . . ?
O3 C10 C11 C6 -178.32(12) . . . . ?
C9 C10 C11 C6 1.7(2) . . . . ?
C7 C6 C11 C10 -0.8(2) . . . . ?
C5 C6 C11 C10 179.94(12) . . . . ?
N2 C3 N1 C2 -0.3(2) . . . . ?
N4 C3 N1 C2 179.98(13) . . . . ?
N3 C2 N1 C3 177.54(14) . . . . ?
C1 C2 N1 C3 -3.2(2) . . . . ?
N1 C3 N2 C4 3.0(2) . . . . ?
N4 C3 N2 C4 -177.28(14) . . . . ?
C1 C4 N2 C3 -2.4(2) . . . . ?
C9 C8 O1 C12 163.56(17) . . . . ?
C7 C8 O1 C12 -18.4(2) . . . . ?
C8 C9 O2 C13 -67.4(2) . . . . ?
C10 C9 O2 C13 115.53(16) . . . . ?
C11 C10 O3 C14 -2.6(2) . . . . ?
C9 C10 O3 C14 177.35(14) . . . . ?
O4 C15 C16 O5 -0.2(2) . . . . ?
C20 C15 C16 O5 177.28(15) . . . . ?
O4 C15 C16 C17 -178.71(15) . . . . ?
C20 C15 C16 C17 -1.2(2) . . . . ?
O5 C16 C17 C18 -177.94(19) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C16 C17 C18 C19 0.6(4) . . . . ?
C17 C18 C19 C20 -1.1(4) . . . . ?
O4 C15 C20 C19 178.02(17) . . . . ?
C16 C15 C20 C19 0.7(3) . . . . ?
C18 C19 C20 C15 0.4(3) . . . . ?
