#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/74/4507414.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_4507414
loop_
_publ_author_name
'Elacqua, Elizabeth'
'Bučar, Dejan-Krešimir'
'Henry, Rodger F.'
'Zhang, Geoff G. Z.'
'MacGillivray, Leonard R.'
_publ_contact_author             'Leonard R. MacGillivray'
_publ_section_title
;
 Supramolecular Complexes of Sulfadiazine and Pyridines: Reconfigurable
 Exteriors and Chameleon-like Behavior of Tautomers at the
 Co-Crystal--Salt Boundary
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              393
_journal_paper_doi               10.1021/cg301745x
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C10 H10 S1 O2 N4, (C12 H10 N2)0.5'
_chemical_formula_sum            'C16 H15 N5 O2 S'
_chemical_formula_weight         341.39
_chemical_name_common            'sulfadiazine (E)-1,2-bis(4-pyridyl)ethylene'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.292(4)
_cell_angle_beta                 98.831(3)
_cell_angle_gamma                102.779(3)
_cell_formula_units_Z            2
_cell_length_a                   5.7617(12)
_cell_length_b                   7.9548(17)
_cell_length_c                   18.104(4)
_cell_measurement_reflns_used    970
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.428
_cell_measurement_theta_min      2.6715
_cell_volume                     785.8(3)
_computing_cell_refinement       'Bruker saintplus (Bruker 1999)'
_computing_data_collection       'Bruker SMART (Bruker 2001)'
_computing_data_reduction        'Bruker saintplus (Bruker 1999)'
_computing_molecular_graphics    'ORTEP-3 for Windows v2.01'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega 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  0.0717
_diffrn_reflns_av_sigmaI/netI    0.0565
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9435
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.16
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelapiped
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0472
_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)+(0.0756P)²+0.1470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1410
_reflns_number_gt                3057
_reflns_number_total             3726
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg301745x_si_005.cif
_cod_data_source_block           (SDZ)(bpe)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4507414
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.92760(8) 1.00964(6) 0.18337(2) 0.03007(16) Uani 1 1 d .
O1 O 1.1571(2) 1.13779(18) 0.20362(7) 0.0345(3) Uani 1 1 d .
O2 O 0.7179(2) 1.05770(19) 0.20368(8) 0.0371(3) Uani 1 1 d .
N1 N 1.0754(3) 0.4130(2) 0.32610(11) 0.0369(4) Uani 1 1 d .
H1NA H 1.153(5) 0.345(3) 0.3088(15) 0.049(7) Uiso 1 1 d .
H1NB H 0.975(4) 0.371(3) 0.3515(14) 0.046(7) Uiso 1 1 d .
N2 N 0.8958(3) 0.9583(2) 0.09059(8) 0.0332(4) Uani 1 1 d .
H2N H 1.0166 1.0031 0.0710 0.040 Uiso 1 1 calc R
N3 N 0.7070(3) 0.8451(2) -0.03278(9) 0.0316(4) Uani 1 1 d .
N4 N 0.5150(3) 0.7633(2) 0.06928(9) 0.0397(4) Uani 1 1 d .
C1 C 1.0283(3) 0.5405(2) 0.28769(10) 0.0299(4) Uani 1 1 d .
C2 C 1.1781(3) 0.6056(3) 0.23829(11) 0.0330(4) Uani 1 1 d .
H2 H 1.3007 0.5524 0.2277 0.040 Uiso 1 1 calc R
C3 C 1.1462(3) 0.7463(3) 0.20549(10) 0.0326(4) Uani 1 1 d .
H3 H 1.2504 0.7907 0.1746 0.039 Uiso 1 1 calc R
C4 C 0.9569(3) 0.8221(2) 0.21874(10) 0.0286(4) Uani 1 1 d .
C5 C 0.8003(3) 0.7557(3) 0.26502(10) 0.0317(4) Uani 1 1 d .
H5 H 0.6719 0.8050 0.2729 0.038 Uiso 1 1 calc R
C6 C 0.8358(3) 0.6174(3) 0.29897(11) 0.0332(4) Uani 1 1 d .
H6 H 0.7310 0.5739 0.3299 0.040 Uiso 1 1 calc R
C7 C 0.6950(3) 0.8508(2) 0.04098(10) 0.0295(4) Uani 1 1 d .
C8 C 0.5151(4) 0.7431(3) -0.08252(11) 0.0374(4) Uani 1 1 d .
H8 H 0.5156 0.7355 -0.1342 0.045 Uiso 1 1 calc R
C9 C 0.3154(4) 0.6484(3) -0.05986(13) 0.0470(5) Uani 1 1 d .
H9 H 0.1813 0.5784 -0.0948 0.056 Uiso 1 1 calc R
C10 C 0.3265(4) 0.6636(3) 0.01722(13) 0.0477(6) Uani 1 1 d .
H10 H 0.1952 0.6009 0.0342 0.057 Uiso 1 1 calc R
N5 N 0.6910(3) 0.2859(2) 0.41516(10) 0.0395(4) Uani 1 1 d .
C11 C 0.5030(4) 0.1592(3) 0.37498(12) 0.0398(5) Uani 1 1 d .
H11 H 0.5035 0.1211 0.3240 0.048 Uiso 1 1 calc R
C12 C 0.3079(4) 0.0811(3) 0.40452(11) 0.0384(5) Uani 1 1 d .
H12 H 0.1827 -0.0073 0.3737 0.046 Uiso 1 1 calc R
C13 C 0.2991(3) 0.1348(2) 0.48033(11) 0.0316(4) Uani 1 1 d .
C14 C 0.4957(4) 0.2658(3) 0.52248(12) 0.0392(5) Uani 1 1 d .
H14 H 0.5007 0.3059 0.5737 0.047 Uiso 1 1 calc R
C15 C 0.6830(4) 0.3363(3) 0.48833(13) 0.0423(5) Uani 1 1 d .
H15 H 0.8116 0.4241 0.5179 0.051 Uiso 1 1 calc R
C16 C 0.1001(3) 0.0602(3) 0.51676(11) 0.0347(4) Uani 1 1 d .
H16 H 0.1164 0.1015 0.5685 0.042 Uiso 1 1 calc R
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
O2 S1 O1 118.90(9) .
O2 S1 N2 110.79(8) .
O1 S1 N2 102.07(8) .
O2 S1 C4 108.78(8) .
O1 S1 C4 109.14(8) .
N2 S1 C4 106.39(9) .
C1 N1 H1NA 119.6(18) .
C1 N1 H1NB 118.4(17) .
H1NA N1 H1NB 115(2) .
C7 N2 S1 126.55(13) .
C7 N2 H2N 116.7 .
S1 N2 H2N 116.7 .
C8 N3 C7 116.02(16) .
C7 N4 C10 114.80(17) .
N1 C1 C6 121.00(18) .
N1 C1 C2 121.00(18) .
C6 C1 C2 117.93(17) .
C3 C2 C1 121.13(17) .
C3 C2 H2 119.4 .
C1 C2 H2 119.4 .
C2 C3 C4 119.70(17) .
C2 C3 H3 120.2 .
C4 C3 H3 120.2 .
C3 C4 C5 120.25(18) .
C3 C4 S1 120.17(14) .
C5 C4 S1 119.42(14) .
C6 C5 C4 119.88(17) .
C6 C5 H5 120.1 .
C4 C5 H5 120.1 .
C5 C6 C1 121.02(17) .
C5 C6 H6 119.5 .
C1 C6 H6 119.5 .
N4 C7 N3 126.92(17) .
N4 C7 N2 118.76(16) .
N3 C7 N2 114.31(15) .
N3 C8 C9 122.26(18) .
N3 C8 H8 118.9 .
C9 C8 H8 118.9 .
C10 C9 C8 116.12(19) .
C10 C9 H9 121.9 .
C8 C9 H9 121.9 .
N4 C10 C9 123.87(19) .
N4 C10 H10 118.1 .
C9 C10 H10 118.1 .
C11 N5 C15 115.97(17) .
N5 C11 C12 124.01(19) .
N5 C11 H11 118.0 .
C12 C11 H11 118.0 .
C11 C12 C13 119.90(19) .
C11 C12 H12 120.1 .
C13 C12 H12 120.1 .
C12 C13 C14 116.20(17) .
C12 C13 C16 123.91(18) .
C14 C13 C16 119.89(17) .
C15 C14 C13 120.00(19) .
C15 C14 H14 120.0 .
C13 C14 H14 120.0 .
N5 C15 C14 123.9(2) .
N5 C15 H15 118.0 .
C14 C15 H15 118.0 .
C16 C16 C13 126.3(2) 2_556
C16 C16 H16 116.8 2_556
C13 C16 H16 116.8 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.4289(14) .
S1 O1 1.4383(14) .
S1 N2 1.6421(16) .
S1 C4 1.7372(19) .
N1 C1 1.361(3) .
N1 H1NA 0.84(3) .
N1 H1NB 0.83(3) .
N2 C7 1.378(2) .
N2 H2N 0.8600 .
N3 C8 1.333(2) .
N3 C7 1.342(2) .
N4 C7 1.330(2) .
N4 C10 1.336(3) .
C1 C6 1.407(3) .
C1 C2 1.409(3) .
C2 C3 1.374(3) .
C2 H2 0.9300 .
C3 C4 1.393(3) .
C3 H3 0.9300 .
C4 C5 1.395(2) .
C5 C6 1.373(3) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C8 C9 1.382(3) .
C8 H8 0.9300 .
C9 C10 1.374(3) .
C9 H9 0.9300 .
C10 H10 0.9300 .
N5 C11 1.335(3) .
N5 C15 1.338(3) .
C11 C12 1.381(3) .
C11 H11 0.9300 .
C12 C13 1.389(3) .
C12 H12 0.9300 .
C13 C14 1.391(3) .
C13 C16 1.465(3) .
C14 C15 1.378(3) .
C14 H14 0.9300 .
C15 H15 0.9300 .
C16 C16 1.321(4) 2_556
C16 H16 0.9300 .
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
N1 H1NA O1 0.84(3) 2.34(3) 3.051(2) 144(2) 1_545
N1 H1NB N5 0.83(3) 2.19(3) 3.017(3) 173(2) .
N2 H2N N3 0.86 2.05 2.899(2) 169.0 2_775
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_4
O2 S1 N2 C7 -46.42(19) .
O1 S1 N2 C7 -174.00(16) .
C4 S1 N2 C7 71.65(18) .
N1 C1 C2 C3 -173.27(18) .
C6 C1 C2 C3 3.6(3) .
C1 C2 C3 C4 -2.5(3) .
C2 C3 C4 C5 0.0(3) .
C2 C3 C4 S1 175.31(14) .
O2 S1 C4 C3 178.93(14) .
O1 S1 C4 C3 -49.90(17) .
N2 S1 C4 C3 59.54(16) .
O2 S1 C4 C5 -5.69(17) .
O1 S1 C4 C5 125.48(15) .
N2 S1 C4 C5 -125.08(15) .
C3 C4 C5 C6 1.4(3) .
S1 C4 C5 C6 -173.99(14) .
C4 C5 C6 C1 -0.2(3) .
N1 C1 C6 C5 174.64(18) .
C2 C1 C6 C5 -2.3(3) .
C10 N4 C7 N3 -1.6(3) .
C10 N4 C7 N2 179.36(19) .
C8 N3 C7 N4 1.4(3) .
C8 N3 C7 N2 -179.59(17) .
S1 N2 C7 N4 -7.4(3) .
S1 N2 C7 N3 173.48(14) .
C7 N3 C8 C9 -0.1(3) .
N3 C8 C9 C10 -0.7(4) .
C7 N4 C10 C9 0.7(4) .
C8 C9 C10 N4 0.4(4) .
C15 N5 C11 C12 0.1(3) .
N5 C11 C12 C13 0.5(3) .
C11 C12 C13 C14 -0.9(3) .
C11 C12 C13 C16 179.95(19) .
C12 C13 C14 C15 0.8(3) .
C16 C13 C14 C15 -180.0(2) .
C11 N5 C15 C14 -0.2(3) .
C13 C14 C15 N5 -0.3(3) .
C12 C13 C16 C16 -3.2(4) 2_556
C14 C13 C16 C16 177.7(3) 2_556
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146402
