#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:38:02 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179539 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/08/4500819.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_4500819
loop_
_publ_author_name
'Ghosh, Soumyajit'
'Bag, Partha Pratim'
'Reddy, C. Malla'
_publ_section_title
;
 Co-Crystals of Sulfamethazine with Some Carboxylic Acids and Amides:
 Co-Former Assisted Tautomerism in an Active Pharmaceutical Ingredient and
 Hydrogen Bond Competition Study
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3489
_journal_paper_doi               10.1021/cg200334m
_journal_volume                  11
_journal_year                    2011
_chemical_formula_moiety         '2(C12 H14 N4 O2 S), C4 H4 O4, C2 H3 N'
_chemical_formula_sum            'C30 H35 N9 O8 S2'
_chemical_formula_weight         713.79
_chemical_melting_point          472
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4148(7)
_cell_length_b                   20.1672(12)
_cell_length_c                   14.8653(9)
_cell_measurement_reflns_used    9685
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.03
_cell_measurement_theta_min      2.47
_cell_volume                     3422.1(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15901
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'multi-scan absorption correction'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.812
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3730
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.812
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0349
_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)+(0.0809P)²+3.3723P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1091
_reflns_number_gt                3286
_reflns_number_total             3730
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200334m_si_002.cif
_cod_data_source_block           cmr_sg_61a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'Pbcn '
_cod_database_code               4500819
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'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
S1 S 0.23295(3) 0.130473(17) 0.32020(2) 0.01801(12) Uani 1 1 d .
N3 N 0.28826(11) 0.05667(6) 0.30378(8) 0.0182(3) Uani 1 1 d .
O2 O 0.10898(10) 0.12469(5) 0.33370(7) 0.0252(2) Uani 1 1 d .
O3 O 0.27475(10) 0.16666(5) 0.24339(7) 0.0254(3) Uani 1 1 d .
O4 O 0.42576(10) 1.03954(5) 0.15064(7) 0.0268(3) Uani 1 1 d .
N1 N 0.30823(11) -0.05543(6) 0.32048(8) 0.0183(3) Uani 1 1 d .
N2 N 0.21120(10) 0.00877(6) 0.43339(8) 0.0201(3) Uani 1 1 d .
O5 O 0.39843(10) 0.92964(5) 0.15434(7) 0.0256(2) Uani 1 1 d .
C15 C 0.47925(12) 0.97487(7) 0.02341(9) 0.0201(3) Uani 1 1 d .
C1 C 0.33745(18) -0.17394(8) 0.33056(13) 0.0353(4) Uani 1 1 d .
H1A H 0.3045 -0.1803 0.2718 0.053 Uiso 1 1 calc R
H1B H 0.3159 -0.2104 0.3687 0.053 Uiso 1 1 calc R
H1C H 0.4212 -0.1717 0.3261 0.053 Uiso 1 1 calc R
C2 C 0.29193(14) -0.11082(7) 0.36975(11) 0.0240(3) Uani 1 1 d .
C3 C 0.26715(11) 0.00129(7) 0.35585(9) 0.0166(3) Uani 1 1 d .
C4 C 0.29461(13) 0.16490(6) 0.41636(9) 0.0176(3) Uani 1 1 d .
C5 C 0.22720(12) 0.17161(7) 0.49384(9) 0.0185(3) Uani 1 1 d .
H5 H 0.1539 0.1516 0.4973 0.022 Uiso 1 1 calc R
C6 C 0.26923(12) 0.20790(7) 0.56548(9) 0.0193(3) Uani 1 1 d .
H6 H 0.2235 0.2129 0.6168 0.023 Uiso 1 1 calc R
C7 C 0.38043(13) 0.23743(7) 0.56167(9) 0.0193(3) Uani 1 1 d .
N4 N 0.41985(12) 0.27465(7) 0.63189(9) 0.0254(3) Uani 1 1 d .
C9 C 0.23601(14) -0.10769(8) 0.45198(12) 0.0281(3) Uani 1 1 d .
H9 H 0.2258 -0.1457 0.4866 0.034 Uiso 1 1 calc R
C10 C 0.19539(13) -0.04679(8) 0.48179(10) 0.0243(3) Uani 1 1 d .
C11 C 0.40667(13) 0.19216(7) 0.41206(10) 0.0219(3) Uani 1 1 d .
H11 H 0.4522 0.1867 0.3607 0.026 Uiso 1 1 calc R
C12 C 0.44936(13) 0.22724(7) 0.48453(10) 0.0233(3) Uani 1 1 d .
H12 H 0.5249 0.2444 0.4824 0.028 Uiso 1 1 calc R
C13 C 0.13202(16) -0.03946(10) 0.56930(11) 0.0351(4) Uani 1 1 d .
H13A H 0.1454 0.0042 0.5930 0.053 Uiso 1 1 calc R
H13B H 0.1604 -0.0719 0.6112 0.053 Uiso 1 1 calc R
H13C H 0.0496 -0.0459 0.5599 0.053 Uiso 1 1 calc R
C14 C 0.43189(12) 0.98497(7) 0.11575(9) 0.0194(3) Uani 1 1 d .
H15 H 0.4784(16) 0.9308(10) 0.0027(12) 0.027(5) Uiso 1 1 d .
H4A H 0.3682(19) 0.2881(10) 0.6739(14) 0.035(5) Uiso 1 1 d .
H4B H 0.4822(18) 0.2980(10) 0.6274(12) 0.026(5) Uiso 1 1 d .
C18 C 0.0000 0.0456(3) 0.7500 0.1075(19) Uani 1 2 d S
C17 C 0.0171(4) 0.1052(4) 0.7137(3) 0.086(2) Uani 0.50 1 d P
N5 N 0.0406(5) 0.1498(4) 0.6721(5) 0.128(3) Uani 0.50 1 d P
H3 H 0.3362(16) 0.0532(9) 0.2577(14) 0.026(5) Uiso 1 1 d .
H5A H 0.3680(19) 0.9391(11) 0.2100(15) 0.040(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'
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
O2 S1 O3 118.70(7) . .
O2 S1 N3 109.14(7) . .
O3 S1 N3 102.45(6) . .
O2 S1 C4 108.48(7) . .
O3 S1 C4 108.44(7) . .
N3 S1 C4 109.27(6) . .
C3 N3 S1 125.85(10) . .
C3 N3 H3 118.8(12) . .
S1 N3 H3 115.4(12) . .
C3 N1 C2 116.39(13) . .
C3 N2 C10 115.79(13) . .
C14 O5 H5A 109.1(13) . .
C15 C15 C14 120.80(16) 5_675 .
C15 C15 H15 123.9(11) 5_675 .
C14 C15 H15 115.3(11) . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
N1 C2 C9 120.45(14) . .
N1 C2 C1 116.50(14) . .
C9 C2 C1 123.04(15) . .
N2 C3 N1 127.23(13) . .
N2 C3 N3 118.65(13) . .
N1 C3 N3 114.12(12) . .
C5 C4 C11 120.47(13) . .
C5 C4 S1 119.71(11) . .
C11 C4 S1 119.44(11) . .
C6 C5 C4 119.91(13) . .
C6 C5 H5 120.0 . .
C4 C5 H5 120.0 . .
C5 C6 C7 120.59(13) . .
C5 C6 H6 119.7 . .
C7 C6 H6 119.7 . .
N4 C7 C6 120.11(13) . .
N4 C7 C12 121.39(14) . .
C6 C7 C12 118.50(13) . .
C7 N4 H4A 118.8(13) . .
C7 N4 H4B 121.2(13) . .
H4A N4 H4B 115.6(18) . .
C2 C9 C10 118.58(14) . .
C2 C9 H9 120.7 . .
C10 C9 H9 120.7 . .
N2 C10 C9 121.53(14) . .
N2 C10 C13 116.62(14) . .
C9 C10 C13 121.85(15) . .
C12 C11 C4 119.42(13) . .
C12 C11 H11 120.3 . .
C4 C11 H11 120.3 . .
C11 C12 C7 120.99(14) . .
C11 C12 H12 119.5 . .
C7 C12 H12 119.5 . .
C10 C13 H13A 109.5 . .
C10 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C10 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
O4 C14 O5 124.43(13) . .
O4 C14 C15 122.46(13) . .
O5 C14 C15 113.11(12) . .
C17 C18 C17 51.1(6) . 3_556
N5 C17 C17 126.7(6) . 3_556
N5 C17 C18 168.6(8) . .
C17 C17 C18 64.5(3) 3_556 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.4341(12) .
S1 O3 1.4367(11) .
S1 N3 1.6352(12) .
S1 C4 1.7380(14) .
N3 C3 1.3800(18) .
N3 H3 0.88(2) .
O4 C14 1.2186(17) .
N1 C3 1.3434(18) .
N1 C2 1.3487(19) .
N2 C3 1.3264(18) .
N2 C10 1.3438(19) .
O5 C14 1.3116(18) .
O5 H5A 0.92(2) .
C15 C15 1.318(3) 5_675
C15 C14 1.4893(19) .
C15 H15 0.940(19) .
C1 C2 1.493(2) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C9 1.380(2) .
C4 C5 1.3917(19) .
C4 C11 1.394(2) .
C5 C6 1.379(2) .
C5 H5 0.9300 .
C6 C7 1.403(2) .
C6 H6 0.9300 .
C7 N4 1.3622(18) .
C7 C12 1.406(2) .
N4 H4A 0.90(2) .
N4 H4B 0.86(2) .
C9 C10 1.386(2) .
C9 H9 0.9300 .
C10 C13 1.496(2) .
C11 C12 1.378(2) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C18 C17 1.330(8) .
C18 C17 1.330(8) 3_556
C17 N5 1.125(8) .
C17 C17 1.147(10) 3_556
