An X-ray crystallographic and density functional theory study of (3<i>Z</i>)-4-(5-ethylsulfonyl-2-hydroxyanilino)pent-3-en-2-one and (3<i>Z</i>)-4-(5-<i>tert</i>-butyl-2-hydroxyanilino)pent-3-en-2-one
Akerman, Kate J.; Munro, Orde Q.; Acta Crystallographica Section C 69 (2013) 258–262; doi:10.1107/S0108270113002369

data_2018850
_publ_section_title
;
 An X-ray crystallographic and density functional theory study of
 (3<i>Z</i>)-4-(5-ethylsulfonyl-2-hydroxyanilino)pent-3-en-2-one and
 (3<i>Z</i>)-4-(5-<i>tert</i>-butyl-2-hydroxyanilino)pent-3-en-2-one
;
_journal_coeditor_code           YP3023
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              258
_journal_page_last               262
_journal_paper_doi               10.1107/S0108270113002369
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C13 H17 N O4 S'
_chemical_formula_moiety         'C13 H17 N O4 S'
_chemical_formula_sum            'C13 H17 N O4 S'
_chemical_formula_weight         283.34
_chemical_name_systematic
;
(3<i>Z</i>)-4-(5-Ethylsulfonyl-2-hydroxyanilino)pent-3-en-2-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2335(6)
_cell_length_b                   8.9651(8)
_cell_length_c                   24.747(2)
_cell_measurement_reflns_used    2673
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      1.6
_cell_volume                     1383.0(2)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics    'WinGX (Farrugia, 2012)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX DUO'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Incoatec Microsource'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0142
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6386
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.65
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.9089
_exptl_absorpt_correction_T_min  0.8983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2010)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.274
_refine_ls_abs_structure_details 'Flack (1983), with 1051 Friedel pairs'
_refine_ls_abs_structure_Flack   0.13(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2703
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0229
_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/[\s^2^(Fo^2^)+(0.0281P)^2^+0.3817P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0592
_refine_ls_wR_factor_ref         0.0598
_reflns_number_gt                2673
_reflns_number_total             2703
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            yp3023.cif
_cod_data_source_block           I
_cod_database_code               2018850
_cod_database_fobs_code          2018850