#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/45/7204594.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_7204594
loop_
_publ_author_name
'Baskar Raj, S.'
'Sethuraman, V.'
'Francis, S.'
'Hemamalini, M.'
'Muthiah, P. Thomas'
'Bocelli, G.'
'Cantoni, A.'
'Rychlewska, U.'
'Warzajtis, B.'
_publ_section_title
;
 Supramolecular organisation via hydrogen bonding in trimethoprim
 sulfonate salts
;
_journal_issue                   15
_journal_name_full               CrystEngComm
_journal_page_first              70
_journal_paper_doi               10.1039/b300126a
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C21 H26 N4 O6 S'
_chemical_formula_weight         462.52
_chemical_name_common            'Trimethoprim p-toluenesulfonate'
_chemical_name_systematic
;
[2,4-diamino-5-(3',4',5'-trimethoxybenzyl pyrimidinium)]
4-methylbenzene sulfonate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.60(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.407(3)
_cell_length_b                   10.039(3)
_cell_length_c                   17.115(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_volume                     2303.4(13)
_computing_cell_refinement       'CAD4 Enraf-Nonius'
_computing_data_collection       'CAD4 Enraf-Nonius'
_computing_data_reduction        'CAD4 Enraf-Nonius'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CAD-4 Enraf Nonius'
_diffrn_measurement_method       'ω-2 scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4216
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.35
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0171(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0564P)²+0.8259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1158
_reflns_number_gt                2868
_reflns_number_total             4031
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b300126a.txt
_cod_data_source_block           for_compound_3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7204594
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, -z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.61380(15) 0.5647(2) 0.34279(11) 0.0397(5) Uani 1 1 d . . .
C4 C 0.50119(15) 0.6756(2) 0.41966(11) 0.0403(5) Uani 1 1 d . . .
C5 C 0.49299(15) 0.7835(2) 0.36473(11) 0.0386(5) Uani 1 1 d . . .
C6 C 0.55281(16) 0.7728(2) 0.30261(12) 0.0412(5) Uani 1 1 d . . .
C7 C 0.4228(2) 0.9003(3) 0.37712(14) 0.0541(6) Uani 1 1 d . . .
C8 C 0.38962(18) 0.9670(2) 0.30153(13) 0.0498(6) Uani 1 1 d . . .
C9 C 0.4538(2) 1.0514(2) 0.26208(14) 0.0526(6) Uani 1 1 d . . .
C10 C 0.42418(18) 1.1065(2) 0.19078(14) 0.0534(6) Uani 1 1 d . . .
C11 C 0.33042(19) 1.0804(2) 0.16074(15) 0.0592(6) Uani 1 1 d . . .
C12 C 0.26628(19) 0.9966(3) 0.20086(16) 0.0633(7) Uani 1 1 d . . .
C13 C 0.2966(2) 0.9401(3) 0.27124(16) 0.0592(7) Uani 1 1 d . . .
C14 C 0.5830(2) 1.2047(4) 0.1683(2) 0.0993(11) Uani 1 1 d . . .
H14A H 0.6145 1.2653 0.1329 0.149 Uiso 1 1 calc R . .
H14B H 0.6158 1.1197 0.1660 0.149 Uiso 1 1 calc R . .
H14C H 0.5879 1.2392 0.2205 0.149 Uiso 1 1 calc R . .
C15 C 0.3152(4) 1.0651(4) 0.0249(2) 0.1258(16) Uani 1 1 d . . .
H15A H 0.2794 0.9826 0.0288 0.189 Uiso 1 1 calc R . .
H15B H 0.3852 1.0471 0.0198 0.189 Uiso 1 1 calc R . .
H15C H 0.2919 1.1136 -0.0201 0.189 Uiso 1 1 calc R . .
C16 C 0.1160(2) 0.8697(4) 0.1946(2) 0.1027(12) Uani 1 1 d . . .
H16A H 0.0548 0.8646 0.1652 0.154 Uiso 1 1 calc R . .
H16B H 0.1016 0.8858 0.2486 0.154 Uiso 1 1 calc R . .
H16C H 0.1516 0.7872 0.1898 0.154 Uiso 1 1 calc R . .
C17 C 0.72178(16) 0.5178(2) 0.04547(12) 0.0438(5) Uani 1 1 d . . .
C18 C 0.6452(2) 0.5745(3) 0.00409(16) 0.0669(7) Uani 1 1 d . . .
C19 C 0.6051(3) 0.5087(3) -0.06023(19) 0.0802(9) Uani 1 1 d . . .
C20 C 0.6400(2) 0.3863(3) -0.08243(16) 0.0690(7) Uani 1 1 d . . .
C21 C 0.7179(3) 0.3327(3) -0.04154(18) 0.0757(8) Uani 1 1 d . . .
C22 C 0.7597(2) 0.3970(3) 0.02226(16) 0.0646(7) Uani 1 1 d . . .
C23 C 0.5926(3) 0.3147(4) -0.1514(2) 0.1095(12) Uani 1 1 d . . .
H23A H 0.5391 0.3678 -0.1724 0.164 Uiso 1 1 calc R . .
H23B H 0.5669 0.2303 -0.1345 0.164 Uiso 1 1 calc R . .
H23C H 0.6418 0.3006 -0.1909 0.164 Uiso 1 1 calc R . .
N1 N 0.61384(13) 0.66705(17) 0.29197(10) 0.0414(4) Uani 1 1 d . . .
N2 N 0.67049(18) 0.4602(2) 0.32754(13) 0.0585(6) Uani 1 1 d . . .
N3 N 0.55833(13) 0.56767(17) 0.40670(9) 0.0435(4) Uani 1 1 d . . .
N4 N 0.45282(17) 0.6777(2) 0.48664(11) 0.0562(6) Uani 1 1 d . . .
O1 O 0.48226(14) 1.18971(18) 0.14721(11) 0.0730(6) Uani 1 1 d . . .
O2 O 0.29946(15) 1.1411(2) 0.09223(12) 0.0812(6) Uani 1 1 d . . .
O3 O 0.17536(15) 0.9753(2) 0.16529(14) 0.0955(8) Uani 1 1 d . . .
O4 O 0.86736(13) 0.6584(2) 0.10124(9) 0.0707(5) Uani 1 1 d . . .
O5 O 0.78838(12) 0.50000(17) 0.18758(8) 0.0569(4) Uani 1 1 d . . .
O6 O 0.70392(13) 0.70273(16) 0.15011(9) 0.0606(5) Uani 1 1 d . . .
S1 S 0.77460(4) 0.60019(6) 0.12691(3) 0.04697(19) Uani 1 1 d . . .
H1 H 0.6496(18) 0.667(3) 0.2496(16) 0.064(7) Uiso 1 1 d . . .
H2A H 0.705(2) 0.461(3) 0.2908(17) 0.067(9) Uiso 1 1 d . . .
H2B H 0.663(2) 0.388(3) 0.3546(17) 0.078(9) Uiso 1 1 d . . .
H4A H 0.4529(19) 0.605(3) 0.5165(16) 0.069(8) Uiso 1 1 d . . .
H4B H 0.4139(19) 0.743(3) 0.4991(15) 0.065(8) Uiso 1 1 d . . .
H6 H 0.5575(14) 0.836(2) 0.2645(12) 0.035(5) Uiso 1 1 d . . .
H7A H 0.4534(18) 0.962(3) 0.4090(15) 0.061(8) Uiso 1 1 d . . .
H7B H 0.362(2) 0.869(3) 0.4058(16) 0.077(8) Uiso 1 1 d . . .
H9 H 0.5155(18) 1.067(2) 0.2827(13) 0.053(7) Uiso 1 1 d . . .
H13 H 0.2548(18) 0.882(3) 0.2962(14) 0.061(7) Uiso 1 1 d . . .
H18 H 0.6192(19) 0.656(3) 0.0175(15) 0.073(8) Uiso 1 1 d . . .
H19 H 0.548(2) 0.545(3) -0.0885(18) 0.102(11) Uiso 1 1 d . . .
H21 H 0.744(2) 0.247(3) -0.0540(19) 0.101(11) Uiso 1 1 d . . .
H22 H 0.811(2) 0.357(3) 0.0482(18) 0.087(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'
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
N2 C2 N3 120.51(19) . . ?
N2 C2 N1 118.27(19) . . ?
N3 C2 N1 121.23(18) . . ?
N4 C4 N3 116.12(19) . . ?
N4 C4 C5 121.3(2) . . ?
N3 C4 C5 122.58(17) . . ?
C6 C5 C4 114.51(19) . . ?
C6 C5 C7 123.25(19) . . ?
C4 C5 C7 122.23(18) . . ?
C5 C6 N1 122.4(2) . . ?
C8 C7 C5 113.42(18) . . ?
C13 C8 C9 120.1(2) . . ?
C13 C8 C7 119.4(2) . . ?
C9 C8 C7 120.4(2) . . ?
C8 C9 C10 119.7(2) . . ?
O1 C10 C11 115.8(2) . . ?
O1 C10 C9 124.1(2) . . ?
C11 C10 C9 120.1(2) . . ?
C10 C11 O2 119.9(2) . . ?
C10 C11 C12 119.8(2) . . ?
O2 C11 C12 120.3(2) . . ?
O3 C12 C13 124.8(2) . . ?
O3 C12 C11 115.2(2) . . ?
C13 C12 C11 119.9(2) . . ?
C8 C13 C12 120.2(2) . . ?
C18 C17 C22 119.8(2) . . ?
C18 C17 S1 120.50(19) . . ?
C22 C17 S1 119.72(19) . . ?
C17 C18 C19 119.7(3) . . ?
C20 C19 C18 121.1(3) . . ?
C21 C20 C19 118.3(3) . . ?
C21 C20 C23 121.7(3) . . ?
C19 C20 C23 120.0(3) . . ?
C20 C21 C22 121.5(3) . . ?
C17 C22 C21 119.5(3) . . ?
C2 N1 C6 120.48(18) . . ?
C2 N3 C4 118.53(17) . . ?
C10 O1 C14 118.5(2) . . ?
C11 O2 C15 114.3(2) . . ?
C12 O3 C16 117.2(2) . . ?
O4 S1 O5 113.11(11) . . ?
O4 S1 O6 111.17(11) . . ?
O5 S1 O6 111.82(10) . . ?
O4 S1 C17 106.79(10) . . ?
O5 S1 C17 106.65(10) . . ?
O6 S1 C17 106.86(10) . . ?
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
C2 N2 1.323(3) . ?
C2 N3 1.330(3) . ?
C2 N1 1.346(3) . ?
C4 N4 1.323(3) . ?
C4 N3 1.347(3) . ?
C4 C5 1.438(3) . ?
C5 C6 1.343(3) . ?
C5 C7 1.519(3) . ?
C6 N1 1.354(3) . ?
C7 C8 1.519(3) . ?
C8 C13 1.373(4) . ?
C8 C9 1.388(3) . ?
C9 C10 1.394(3) . ?
C10 O1 1.369(3) . ?
C10 C11 1.378(3) . ?
C11 O2 1.381(3) . ?
C11 C12 1.390(3) . ?
C12 O3 1.373(3) . ?
C12 C13 1.388(4) . ?
C14 O1 1.403(3) . ?
C15 O2 1.399(4) . ?
C16 O3 1.420(3) . ?
C17 C18 1.366(3) . ?
C17 C22 1.374(3) . ?
C17 S1 1.763(2) . ?
C18 C19 1.387(4) . ?
C19 C20 1.370(4) . ?
C20 C21 1.362(4) . ?
C20 C23 1.516(4) . ?
C21 C22 1.382(4) . ?
O4 S1 1.4465(16) . ?
O5 S1 1.4561(16) . ?
O6 S1 1.4571(17) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21149569
