The imide tautomer of sulfasalazine
Blake, Alexander J.; Lin, Xiang; Schröder, Martin; Wilson, Claire; Yuan, Rong-Xin; Acta Crystallographica Section C 60 (2004) o226–o228; doi:10.1107/S0108270104003026

data_2014052
_publ_section_title
;
 The imide tautomer of sulfasalazine
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o226
_journal_page_last               o228
_journal_paper_doi               10.1107/S0108270104003026
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C18 H14 N4 O5 S'
_chemical_formula_moiety         'C18 H14 N4 O5 S'
_chemical_formula_sum            'C18 H14 N4 O5 S'
_chemical_formula_weight         398.39
_chemical_name_systematic
;
5-{4-[(2-pyridylideneamino)sulfonyl]phenyldiazenyl}salicylic acid
;
_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   'see text'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'enCIFer editing of SHELXL97 output'
_cell_angle_alpha                90.00
_cell_angle_beta                 113.405(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.308(3)
_cell_length_b                   6.0911(11)
_cell_length_c                   16.109(3)
_cell_measurement_reflns_used    2040
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.5
_cell_volume                     1738.6(5)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT and SHELXTL (Bruker, 2001)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'enCIFer (CCDC, 2003) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_av_sigmaI/netI    0.050
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10720
_diffrn_reflns_theta_full        27.40
_diffrn_reflns_theta_max         27.40
_diffrn_reflns_theta_min         2.53
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.02
_refine_diff_density_min         -0.44
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3950
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.104
_refine_ls_R_factor_gt           0.0665
_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/[\s^2^(Fo^2^)+(0.109P)^2^+1.095P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.166
_refine_ls_wR_factor_ref         0.195
_reflns_number_gt                2603
_reflns_number_total             3950
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sk1702.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (8 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (8
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (10
times).

'_geom_torsion_publ_flag' value 'Yes' changed to 'yes'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (11
times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' 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_cell_volume        1738.7(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2014052
_cod_database_fobs_code          2014052