#------------------------------------------------------------------------------
#$Date: 2019-12-26 21:58:51 +0200 (Thu, 26 Dec 2019) $
#$Revision: 246129 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/18/2311832.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2311832
loop_
_publ_author_name
'Buist, Amanda R.'
'Dennany, Lynn'
'Kennedy, Alan R.'
'Manzie, Craig'
'McPhie, Katherine'
'Walker, Brandon'
_publ_section_title
;
 Eight salt forms of sulfadiazine.
;
_journal_coeditor_code           LG3144
_journal_issue                   'Pt 9'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              900
_journal_page_last               907
_journal_paper_doi               10.1107/S2053229614018725
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C10 H11 N4 O2 S +, B F4 -, H2 O'
_chemical_formula_moiety         'C10 H11 N4 O2 S +, B F4 -, H2 O'
_chemical_formula_sum            'C10 H13 B F4 N4 O3 S'
_chemical_formula_weight         356.11
_chemical_name_systematic
;
2-{[(4-Azaniumylphenyl)sulfonyl]azanidyl}pyrimidin-1-ium tetrafluoroborate
monohydrate
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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                 90.982(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.85390(10)
_cell_length_b                   11.3629(3)
_cell_length_c                   21.2080(6)
_cell_measurement_reflns_used    4378
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.8198
_cell_measurement_theta_min      3.3876
_cell_volume                     1410.49(6)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur E'
_diffrn_measurement_method       'omega scans'
_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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8710
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         3.39
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2010)
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.460
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3549
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0362P)²+0.6973P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0888
_reflns_number_gt                2955
_reflns_number_total             3549
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lg3144sup1.cif
_cod_data_source_block           V
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2311832
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 0.21736(6) 0.24493(3) 1.039691(17) 0.01188(10) Uani d . 1 1
F F1 -0.15946(17) 0.20817(10) 0.74824(5) 0.0301(3) Uani d . 1 1
F F2 0.09745(19) 0.18041(11) 0.82770(5) 0.0312(3) Uani d . 1 1
F F3 0.2036(2) 0.15335(12) 0.72644(6) 0.0434(3) Uani d . 1 1
F F4 0.13039(17) 0.33817(10) 0.76257(5) 0.0273(3) Uani d . 1 1
O O1 0.44811(18) 0.27762(10) 1.05680(5) 0.0175(2) Uani d . 1 1
O O2 0.05509(19) 0.25011(10) 1.09069(5) 0.0164(2) Uani d . 1 1
O O1W -0.4027(2) 0.41744(12) 0.76066(6) 0.0245(3) Uani d D 1 1
N N1 -0.0902(2) 0.55457(13) 0.82772(7) 0.0143(3) Uani d . 1 1
N N2 0.1822(2) 0.11597(11) 1.01075(6) 0.0120(3) Uani d . 1 1
N N3 0.2260(2) -0.01928(12) 0.93253(6) 0.0126(3) Uani d . 1 1
N N4 0.4790(2) 0.14123(12) 0.93657(6) 0.0156(3) Uani d . 1 1
C C1 -0.0140(2) 0.47962(14) 0.88004(7) 0.0117(3) Uani d . 1 1
C C2 0.2045(3) 0.49308(14) 0.90438(8) 0.0157(3) Uani d . 1 1
H H2 0.3052 0.5501 0.8875 0.019 Uiso calc R 1 1
C C3 0.2735(2) 0.42144(14) 0.95408(7) 0.0145(3) Uani d . 1 1
H H3 0.4245 0.4276 0.9709 0.017 Uiso calc R 1 1
C C4 0.1225(2) 0.34096(13) 0.97914(7) 0.0115(3) Uani d . 1 1
C C5 -0.0992(2) 0.33031(14) 0.95543(7) 0.0143(3) Uani d . 1 1
H H5 -0.2030 0.2765 0.9737 0.017 Uiso calc R 1 1
C C6 -0.1662(2) 0.39939(14) 0.90476(7) 0.0143(3) Uani d . 1 1
H H6 -0.3157 0.3919 0.8870 0.017 Uiso calc R 1 1
C C7 0.2996(2) 0.08243(14) 0.95992(7) 0.0114(3) Uani d . 1 1
C C8 0.3297(3) -0.06628(15) 0.88228(7) 0.0153(3) Uani d . 1 1
H H8 0.2755 -0.1376 0.8641 0.018 Uiso calc R 1 1
C C9 0.5143(3) -0.00977(15) 0.85782(8) 0.0177(3) Uani d . 1 1
H H9 0.5934 -0.0405 0.8227 0.021 Uiso calc R 1 1
C C10 0.5806(3) 0.09446(16) 0.88665(8) 0.0184(3) Uani d . 1 1
H H10 0.7071 0.1354 0.8697 0.022 Uiso calc R 1 1
B B1 0.0703(3) 0.21971(18) 0.76723(9) 0.0183(4) Uani d . 1 1
H H1N 0.030(4) 0.5713(19) 0.8011(10) 0.029(6) Uiso d . 1 1
H H2N -0.133(3) 0.623(2) 0.8436(9) 0.025(5) Uiso d . 1 1
H H3N -0.206(4) 0.520(2) 0.8040(11) 0.040(6) Uiso d . 1 1
H H4N 0.103(3) -0.0515(17) 0.9493(9) 0.023(5) Uiso d . 1 1
H H1W -0.5492(16) 0.407(2) 0.7599(12) 0.060(8) Uiso d D 1 1
H H2W -0.355(4) 0.3449(11) 0.7561(12) 0.053(8) Uiso d D 1 1
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'
F F 0.0171 0.0103 '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'
B B 0.0013 0.0007 '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
O1 S1 O2 115.10(7)
O1 S1 N2 116.50(7)
O2 S1 N2 103.96(7)
O1 S1 C4 107.78(7)
O2 S1 C4 108.33(7)
N2 S1 C4 104.47(7)
H1W O1W H2W 100.6(17)
C1 N1 H1N 110.8(13)
C1 N1 H2N 107.8(13)
H1N N1 H2N 106.0(18)
C1 N1 H3N 112.4(15)
H1N N1 H3N 108.2(19)
H2N N1 H3N 111.5(19)
C7 N2 S1 120.22(11)
C8 N3 C7 122.10(13)
C8 N3 H4N 122.3(13)
C7 N3 H4N 115.6(13)
C10 N4 C7 117.11(14)
C2 C1 C6 122.02(14)
C2 C1 N1 119.22(14)
C6 C1 N1 118.73(13)
C1 C2 C3 118.40(14)
C1 C2 H2 120.8
C3 C2 H2 120.8
C4 C3 C2 120.00(14)
C4 C3 H3 120.0
C2 C3 H3 120.0
C3 C4 C5 121.16(14)
C3 C4 S1 119.46(11)
C5 C4 S1 119.30(12)
C6 C5 C4 118.88(14)
C6 C5 H5 120.6
C4 C5 H5 120.6
C5 C6 C1 119.49(14)
C5 C6 H6 120.3
C1 C6 H6 120.3
N2 C7 N4 124.56(14)
N2 C7 N3 114.91(13)
N4 C7 N3 120.52(13)
N3 C8 C9 118.98(15)
N3 C8 H8 120.5
C9 C8 H8 120.5
C8 C9 C10 116.84(15)
C8 C9 H9 121.6
C10 C9 H9 121.6
N4 C10 C9 124.44(15)
N4 C10 H10 117.8
C9 C10 H10 117.8
F2 B1 F4 110.92(15)
F2 B1 F3 110.39(15)
F4 B1 F3 109.46(15)
F2 B1 F1 109.54(14)
F4 B1 F1 108.13(14)
F3 B1 F1 108.33(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4413(11)
S1 O2 1.4528(11)
S1 N2 1.6006(13)
S1 C4 1.7675(16)
F1 B1 1.404(2)
F2 B1 1.365(2)
F3 B1 1.396(2)
F4 B1 1.395(2)
O1W H1W 0.867(10)
O1W H2W 0.877(9)
N1 C1 1.463(2)
N1 H1N 0.93(2)
N1 H2N 0.88(2)
N1 H3N 0.92(2)
N2 C7 1.3433(18)
N3 C8 1.3460(19)
N3 C7 1.360(2)
N3 H4N 0.89(2)
N4 C10 1.334(2)
N4 C7 1.3463(19)
C1 C2 1.379(2)
C1 C6 1.384(2)
C2 C3 1.386(2)
C2 H2 0.9500
C3 C4 1.384(2)
C3 H3 0.9500
C4 C5 1.389(2)
C5 C6 1.382(2)
C5 H5 0.9500
C6 H6 0.9500
C8 C9 1.367(2)
C8 H8 0.9500
C9 C10 1.385(2)
C9 H9 0.9500
C10 H10 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1N F3 2_556 0.93(2) 1.92(2) 2.7912(17) 156.0(19)
N1 H2N O2 3_567 0.88(2) 2.05(2) 2.8196(19) 144.7(18)
N1 H3N O1W . 0.92(2) 1.87(3) 2.7762(19) 166(2)
N3 H4N N2 3_557 0.89(2) 2.02(2) 2.9092(17) 176.8(19)
N3 H4N O2 3_557 0.89(2) 2.58(2) 3.1307(17) 121.2(15)
O1W H1W F4 1_455 0.867(10) 2.032(12) 2.8790(15) 165(2)
O1W H2W F1 . 0.877(9) 1.937(11) 2.7863(17) 163(2)
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
O1 S1 N2 C7 -55.37(14)
O2 S1 N2 C7 176.88(12)
C4 S1 N2 C7 63.38(13)
C6 C1 C2 C3 1.7(2)
N1 C1 C2 C3 179.84(14)
C1 C2 C3 C4 -1.7(2)
C2 C3 C4 C5 -0.1(2)
C2 C3 C4 S1 176.70(12)
O1 S1 C4 C3 5.16(15)
O2 S1 C4 C3 130.29(13)
N2 S1 C4 C3 -119.36(13)
O1 S1 C4 C5 -178.00(12)
O2 S1 C4 C5 -52.87(14)
N2 S1 C4 C5 57.48(14)
C3 C4 C5 C6 1.9(2)
S1 C4 C5 C6 -174.93(12)
C4 C5 C6 C1 -1.8(2)
C2 C1 C6 C5 0.1(2)
N1 C1 C6 C5 -178.09(14)
S1 N2 C7 N4 12.5(2)
S1 N2 C7 N3 -168.26(11)
C10 N4 C7 N2 178.32(15)
C10 N4 C7 N3 -0.9(2)
C8 N3 C7 N2 -178.12(13)
C8 N3 C7 N4 1.2(2)
C7 N3 C8 C9 -0.3(2)
N3 C8 C9 C10 -0.8(2)
C7 N4 C10 C9 -0.2(2)
C8 C9 C10 N4 1.1(3)
