#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/45/7204596.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_7204596
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_moiety         (C14H19N4O3+),(C6H5SO3-).H20
_chemical_formula_sum            'C20 H26 N4 O7 S'
_chemical_formula_weight         466.51
_chemical_name_common
;
(2,4-diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidinium)
benzenesulfonate, monohydrate.
;
_chemical_name_systematic
;
[2,4-diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidinium] benzenesulfonate,
monohydrate.
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 107.80(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.507(2)
_cell_length_b                   6.323(3)
_cell_length_c                   21.350(2)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    293(2)
_cell_volume                     2250.2(11)
_computing_cell_refinement       'Bruker AXS Smart Single Crystal with CCD'
_computing_data_collection       'Bruker AXS Smart Single Crystal with CCD'
_computing_data_reduction        'Bruker AXS Smart Single Crystal with CCD'
_computing_molecular_graphics    'PLATON (Spek, 1997)'
_computing_publication_material  'PLATON (Spek, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.876
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_device_type  'Bruker AXS Smart diffractometer'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_sigmaI/netI    0.1294
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17125
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.22
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  60
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Plate shaped crystal'
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.714
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         4924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.714
_refine_ls_R_factor_all          0.1560
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0382P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0930
_reflns_number_gt                2022
_reflns_number_total             4924
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b300126a.txt
_cod_data_source_block           for_compound_1
_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/c
_cod_database_code               7204596
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S S 0.62089(4) 0.11062(11) 0.33943(3) 0.0472(2) Uani 1 1 d . . .
N3 N 0.56671(11) 0.3887(3) 0.08150(9) 0.0391(5) Uani 1 1 d . . .
O5 O 0.60077(10) 0.0561(3) 0.39828(8) 0.0565(5) Uani 1 1 d . . .
O2 O 0.98582(10) 0.8850(3) 0.10033(10) 0.0625(5) Uani 1 1 d . . .
N4 N 0.61688(15) 0.6429(4) 0.02933(12) 0.0507(7) Uani 1 1 d . . .
N1 N 0.58715(13) 0.4145(4) 0.19483(12) 0.0467(6) Uani 1 1 d . . .
C5 C 0.64064(14) 0.6865(4) 0.14507(12) 0.0380(6) Uani 1 1 d . . .
O1W O 0.41702(14) 0.9015(4) 0.02286(12) 0.0664(6) Uani 1 1 d . . .
C4 C 0.60749(13) 0.5715(4) 0.08495(12) 0.0367(6) Uani 1 1 d . . .
O1 O 0.95265(10) 0.5796(3) 0.17405(9) 0.0612(5) Uani 1 1 d . . .
O4 O 0.56722(10) 0.0179(3) 0.27973(8) 0.0606(5) Uani 1 1 d . . .
C2 C 0.55547(15) 0.3162(4) 0.13697(14) 0.0401(6) Uani 1 1 d . . .
N2 N 0.51327(15) 0.1407(4) 0.13538(15) 0.0521(7) Uani 1 1 d . . .
C6 C 0.62855(16) 0.5994(5) 0.19876(14) 0.0474(7) Uani 1 1 d . . .
O6 O 0.63000(12) 0.3379(3) 0.33314(9) 0.0639(6) Uani 1 1 d . . .
C7 C 0.68428(17) 0.8931(5) 0.14803(16) 0.0468(7) Uani 1 1 d . . .
C8 C 0.76406(14) 0.8818(4) 0.13406(12) 0.0407(6) Uani 1 1 d . . .
C11 C 0.91085(15) 0.8804(4) 0.10942(13) 0.0462(7) Uani 1 1 d . . .
C12 C 0.85442(16) 1.0327(4) 0.08104(13) 0.0475(7) Uani 1 1 d . . .
C13 C 0.78068(16) 1.0326(4) 0.09302(14) 0.0456(7) Uani 1 1 d . . .
C10 C 0.89373(15) 0.7256(4) 0.14927(13) 0.0453(7) Uani 1 1 d . . .
C18 C 0.77213(19) 0.0997(6) 0.32611(15) 0.0615(8) Uani 1 1 d . . .
O3 O 0.87589(11) 1.1777(3) 0.04177(10) 0.0662(6) Uani 1 1 d . . .
C17 C 0.71596(15) -0.0050(4) 0.34812(13) 0.0455(7) Uani 1 1 d . . .
C9 C 0.81999(16) 0.7275(5) 0.16191(13) 0.0461(7) Uani 1 1 d . . .
C22 C 0.7323(2) -0.2056(5) 0.37479(16) 0.0650(9) Uani 1 1 d . . .
C20 C 0.8616(3) -0.1937(9) 0.3584(2) 0.0972(15) Uani 1 1 d . . .
C16 C 0.8178(3) 1.3305(7) 0.0091(2) 0.0750(11) Uani 1 1 d . . .
C15 C 0.9908(3) 0.7548(8) 0.0471(2) 0.0843(12) Uani 1 1 d . . .
C14 C 0.9378(3) 0.4144(7) 0.2143(2) 0.0753(11) Uani 1 1 d . . .
C19 C 0.8447(2) 0.0033(9) 0.3315(2) 0.0866(13) Uani 1 1 d . . .
C21 C 0.8053(3) -0.2992(7) 0.3795(2) 0.0881(12) Uani 1 1 d . . .
H9 H 0.8100(13) 0.621(3) 0.1875(11) 0.043(7) Uiso 1 1 d . . .
H7B H 0.6914(12) 0.945(3) 0.1910(11) 0.038(7) Uiso 1 1 d . . .
H13 H 0.7430(12) 1.137(3) 0.0761(10) 0.029(6) Uiso 1 1 d . . .
H7A H 0.6502(14) 0.987(4) 0.1161(12) 0.055(8) Uiso 1 1 d . . .
H2A H 0.5090(18) 0.099(5) 0.1740(15) 0.097(12) Uiso 1 1 d . . .
H16B H 0.7682(19) 1.251(5) -0.0197(15) 0.102(13) Uiso 1 1 d . . .
H4A H 0.5972(17) 0.570(5) -0.0089(14) 0.083(11) Uiso 1 1 d . . .
H14C H 0.9839(17) 0.331(4) 0.2234(13) 0.079(11) Uiso 1 1 d . . .
H4B H 0.6377(14) 0.765(4) 0.0280(11) 0.044(8) Uiso 1 1 d . . .
H16A H 0.8428(17) 1.409(4) -0.0179(15) 0.091(11) Uiso 1 1 d . . .
H18 H 0.7587(14) 0.246(4) 0.3093(12) 0.060(9) Uiso 1 1 d . . .
H2W H 0.4054(19) 0.805(5) 0.0532(18) 0.121(14) Uiso 1 1 d . . .
H14B H 0.927(2) 0.477(5) 0.2526(17) 0.114(15) Uiso 1 1 d . . .
H1 H 0.5828(15) 0.370(4) 0.2330(13) 0.073(10) Uiso 1 1 d . . .
H2B H 0.4890(15) 0.070(4) 0.0970(13) 0.061(10) Uiso 1 1 d . . .
H14A H 0.889(2) 0.333(5) 0.1919(17) 0.118(14) Uiso 1 1 d . . .
H16C H 0.8037(16) 1.412(4) 0.0402(14) 0.074(11) Uiso 1 1 d . . .
H22 H 0.6942(17) -0.272(5) 0.3910(14) 0.082(11) Uiso 1 1 d . . .
H15A H 1.042(2) 0.790(5) 0.0445(15) 0.099(12) Uiso 1 1 d . . .
H21 H 0.8157(19) -0.445(5) 0.3986(16) 0.107(13) Uiso 1 1 d . . .
H15C H 0.984(2) 0.587(6) 0.0588(18) 0.129(15) Uiso 1 1 d . . .
H15B H 0.948(2) 0.794(5) 0.0069(18) 0.115(15) Uiso 1 1 d . . .
H20 H 0.914(2) -0.261(5) 0.3638(16) 0.115(13) Uiso 1 1 d . . .
H19 H 0.878(2) 0.081(5) 0.3182(18) 0.116(16) Uiso 1 1 d . . .
H1W H 0.4310(19) 0.837(5) -0.0051(16) 0.097(15) Uiso 1 1 d . . .
H6 H 0.6497(14) 0.661(4) 0.2427(12) 0.060(8) 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
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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
O5 S O4 113.66(11) . . ?
O5 S O6 112.18(11) . . ?
O4 S O6 112.11(12) . . ?
O5 S C17 106.30(12) . . ?
O4 S C17 105.02(12) . . ?
O6 S C17 106.88(13) . . ?
C2 N3 C4 117.6(2) . . ?
C11 O2 C15 113.0(2) . . ?
C2 N1 C6 121.1(2) . . ?
C6 C5 C4 115.4(2) . . ?
C6 C5 C7 122.0(3) . . ?
C4 C5 C7 122.6(2) . . ?
N4 C4 N3 116.8(2) . . ?
N4 C4 C5 120.1(2) . . ?
N3 C4 C5 123.1(2) . . ?
C10 O1 C14 118.3(2) . . ?
N2 C2 N3 119.6(3) . . ?
N2 C2 N1 118.7(3) . . ?
N3 C2 N1 121.6(3) . . ?
C5 C6 N1 121.1(3) . . ?
C5 C7 C8 115.9(2) . . ?
C9 C8 C13 120.0(2) . . ?
C9 C8 C7 121.5(3) . . ?
C13 C8 C7 118.4(3) . . ?
C12 C11 O2 120.4(2) . . ?
C12 C11 C10 120.1(2) . . ?
O2 C11 C10 119.5(2) . . ?
O3 C12 C11 116.2(2) . . ?
O3 C12 C13 123.8(3) . . ?
C11 C12 C13 119.9(3) . . ?
C8 C13 C12 120.2(3) . . ?
O1 C10 C11 115.8(2) . . ?
O1 C10 C9 124.4(3) . . ?
C11 C10 C9 119.8(3) . . ?
C17 C18 C19 119.5(4) . . ?
C12 O3 C16 117.8(2) . . ?
C18 C17 C22 120.0(3) . . ?
C18 C17 S 120.6(2) . . ?
C22 C17 S 119.3(2) . . ?
C8 C9 C10 119.9(3) . . ?
C21 C22 C17 119.5(4) . . ?
C19 C20 C21 119.7(4) . . ?
C20 C19 C18 120.8(4) . . ?
C20 C21 C22 120.5(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
S O5 1.4465(16) . ?
S O4 1.4557(17) . ?
S O6 1.4564(18) . ?
S C17 1.775(3) . ?
N3 C2 1.339(3) . ?
N3 C4 1.348(3) . ?
O2 C11 1.385(3) . ?
O2 C15 1.427(4) . ?
N4 C4 1.327(3) . ?
N1 C2 1.342(3) . ?
N1 C6 1.365(3) . ?
C5 C6 1.345(3) . ?
C5 C4 1.435(3) . ?
C5 C7 1.505(3) . ?
O1 C10 1.365(3) . ?
O1 C14 1.426(4) . ?
C2 N2 1.327(3) . ?
C7 C8 1.517(3) . ?
C8 C9 1.381(3) . ?
C8 C13 1.384(3) . ?
C11 C12 1.380(3) . ?
C11 C10 1.388(3) . ?
C12 O3 1.370(3) . ?
C12 C13 1.391(3) . ?
C10 C9 1.397(3) . ?
C18 C17 1.382(4) . ?
C18 C19 1.382(5) . ?
O3 C16 1.421(4) . ?
C17 C22 1.384(4) . ?
C22 C21 1.384(5) . ?
C20 C19 1.366(6) . ?
C20 C21 1.375(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21149571
