#------------------------------------------------------------------------------
#$Date: 2017-01-08 20:06:26 +0200 (Sun, 08 Jan 2017) $
#$Revision: 190050 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/93/7119373.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_7119373
loop_
_publ_author_name
Celia
Ruiz-Palomero
Stuart
R.
Kennedy
M.
Laura
Soriano
Christopher
D.
Jones
Miguel
Valcarcel
Jonathan
W.
Steed
_publ_section_title
;
 Pharmaceutical crystallization with nanocellulose organogels
;
_journal_name_full               Chem.Commun.
_journal_page_first              7782
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C13 H17 N3 O3 S2'
_chemical_formula_weight         327.42
_chemical_name_common            'Sulfapyridine DMSO solvate'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-04-11 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.4816(5)
_cell_length_b                   12.7531(5)
_cell_length_c                   22.3603(10)
_cell_measurement_reflns_used    129
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      21.92
_cell_measurement_theta_min      3.73
_cell_volume                     2989.0(2)
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8Venture'
_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  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            43314
_diffrn_reflns_theta_full        28.99
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.369
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_recrystallization_method gel
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.239
_exptl_crystal_size_min          0.212
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0374
_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)+(0.0502P)²+1.6936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0968
_reflns_number_gt                3121
_reflns_number_total             3971
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc03088b2.cif
_cod_data_source_block           Sulfapyridine
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7119373
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
S1 S 0.03823(4) 0.97415(3) 0.140192(16) 0.01266(10) Uani 1 1 d . . .
O1 O -0.03740(11) 0.87900(9) 0.13819(5) 0.0182(3) Uani 1 1 d . . .
N1 N -0.26901(14) 1.32481(12) 0.23489(7) 0.0205(3) Uani 1 1 d . . .
S2 S 0.03270(4) 0.47767(3) 0.086499(19) 0.01678(11) Uani 1 1 d . . .
O2 O 0.15497(11) 0.96756(9) 0.17445(5) 0.0188(3) Uani 1 1 d . . .
C2 C -0.19865(14) 1.24206(12) 0.21461(7) 0.0141(3) Uani 1 1 d . . .
O3 O -0.03962(12) 0.57567(10) 0.07227(6) 0.0275(3) Uani 1 1 d . . .
C3 C -0.24770(15) 1.17532(13) 0.17002(7) 0.0140(3) Uani 1 1 d . . .
H3 H -0.3309(19) 1.1864(15) 0.1555(8) 0.017(5) Uiso 1 1 d . . .
C4 C -0.17581(15) 1.09351(12) 0.14844(7) 0.0140(3) Uani 1 1 d . . .
H4 H -0.2090(19) 1.0508(16) 0.1173(9) 0.021(5) Uiso 1 1 d . . .
C5 C -0.05393(14) 1.07481(12) 0.17130(7) 0.0132(3) Uani 1 1 d . . .
C6 C -0.00589(15) 1.13826(13) 0.21636(7) 0.0146(3) Uani 1 1 d . . .
H6 H 0.0765(19) 1.1290(14) 0.2309(8) 0.019(5) Uiso 1 1 d . . .
C7 C -0.07806(15) 1.22014(13) 0.23844(7) 0.0164(3) Uani 1 1 d . . .
H7 H -0.0455(18) 1.2628(15) 0.2693(9) 0.022(5) Uiso 1 1 d . . .
N8 N 0.05961(13) 1.00467(10) 0.07155(6) 0.0137(3) Uani 1 1 d . . .
C9 C 0.11999(14) 1.09557(12) 0.05814(7) 0.0129(3) Uani 1 1 d . . .
N10 N 0.09683(13) 1.13174(10) 0.00210(6) 0.0140(3) Uani 1 1 d . . .
H10 H 0.047(2) 1.0939(17) -0.0206(9) 0.026(6) Uiso 1 1 d . . .
C11 C 0.14350(16) 1.22311(12) -0.01964(7) 0.0173(3) Uani 1 1 d . . .
H11 H 0.1164(19) 1.2399(16) -0.0577(9) 0.025(5) Uiso 1 1 d . . .
C12 C 0.22124(17) 1.28376(13) 0.01484(8) 0.0202(3) Uani 1 1 d . . .
H12 H 0.2509(18) 1.3460(16) -0.0004(8) 0.021(5) Uiso 1 1 d . . .
C13 C 0.25132(16) 1.24866(13) 0.07215(8) 0.0204(4) Uani 1 1 d . . .
H13 H 0.306(2) 1.2905(16) 0.0976(9) 0.027(5) Uiso 1 1 d . . .
C14 C 0.20219(16) 1.15678(13) 0.09402(8) 0.0176(3) Uani 1 1 d . . .
H14 H 0.2208(17) 1.1338(15) 0.1330(8) 0.015(5) Uiso 1 1 d . . .
C15 C 0.02898(19) 0.46303(17) 0.16602(8) 0.0248(4) Uani 1 1 d . . .
C16 C -0.07237(19) 0.37147(16) 0.06944(9) 0.0253(4) Uani 1 1 d . . .
H1A H -0.233(2) 1.3656(17) 0.2588(10) 0.029(6) Uiso 1 1 d . . .
H15A H -0.058(2) 0.4708(16) 0.1791(10) 0.031(6) Uiso 1 1 d . . .
H16A H -0.151(2) 0.3870(17) 0.0892(10) 0.035(6) Uiso 1 1 d . . .
H1B H -0.331(2) 1.3460(17) 0.2112(10) 0.032(6) Uiso 1 1 d . . .
H15B H 0.075(2) 0.5165(17) 0.1827(10) 0.032(6) Uiso 1 1 d . . .
H16B H -0.082(2) 0.3661(18) 0.0269(11) 0.041(6) Uiso 1 1 d . . .
H15C H 0.066(2) 0.4008(18) 0.1764(10) 0.033(6) Uiso 1 1 d . . .
H16C H -0.036(2) 0.3066(18) 0.0835(10) 0.032(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 O1 115.48(7) . .
O2 S1 N8 113.83(7) . .
O1 S1 N8 104.52(7) . .
O2 S1 C5 107.40(7) . .
O1 S1 C5 108.92(7) . .
N8 S1 C5 106.27(7) . .
O3 S2 C16 106.00(9) . .
O3 S2 C15 106.72(9) . .
C16 S2 C15 96.88(10) . .
N1 C2 C7 121.05(15) . .
N1 C2 C3 120.35(15) . .
C7 C2 C3 118.58(14) . .
C4 C3 C2 120.48(15) . .
C3 C4 C5 120.18(15) . .
C6 C5 C4 119.89(14) . .
C6 C5 S1 121.08(12) . .
C4 C5 S1 118.98(12) . .
C7 C6 C5 120.14(15) . .
C6 C7 C2 120.64(15) . .
C9 N8 S1 119.09(11) . .
N8 C9 N10 114.31(14) . .
N8 C9 C14 129.22(15) . .
N10 C9 C14 116.47(14) . .
C11 N10 C9 124.01(14) . .
N10 C11 C12 120.10(16) . .
C11 C12 C13 118.24(16) . .
C14 C13 C12 121.19(16) . .
C13 C14 C9 119.94(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.4461(12) .
S1 O1 1.4502(12) .
S1 N8 1.5993(14) .
S1 C5 1.7507(16) .
N1 C2 1.365(2) .
S2 O3 1.4959(13) .
S2 C16 1.7869(19) .
S2 C15 1.7882(19) .
C2 C7 1.400(2) .
C2 C3 1.408(2) .
C3 C4 1.374(2) .
C4 C5 1.397(2) .
C5 C6 1.387(2) .
C6 C7 1.381(2) .
N8 C9 1.3544(19) .
C9 N10 1.357(2) .
C9 C14 1.413(2) .
N10 C11 1.354(2) .
C11 C12 1.362(2) .
C12 C13 1.394(2) .
C13 C14 1.370(2) .
