Seven 3-methylidene-1<i>H</i>-indol-2(3<i>H</i>)-ones related to the multiple-receptor tyrosine kinase inhibitor sunitinib
Spencer, John; Chowdhry, Babur Z.; Hamid, Samiyah; Mendham, Andrew P.; Male, Louise; Coles, Simon J.; Hursthouse, Michael B.; Acta Crystallographica Section C 66 (2010) o71–o78; doi:10.1107/S0108270109054134

data_2017512
_publ_section_title
;
 Seven 3-methylidene-1<i>H</i>-indol-2(3<i>H</i>)-ones related to the
 multiple-receptor tyrosine kinase inhibitor sunitinib
;
_journal_coeditor_code           GG3207
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o71
_journal_page_last               o78
_journal_paper_doi               10.1107/S0108270109054134
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H9 N O S'
_chemical_formula_moiety         'C13 H9 N O S'
_chemical_formula_sum            'C13 H9 N O S'
_chemical_formula_weight         227.27
_chemical_name_systematic
;
(3<i>Z</i>)-3-(2-thienylmethylidene)-1<i>H</i>-indol-2(3<i>H</i>)-one
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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            8
_cell_length_a                   11.9297(5)
_cell_length_b                   10.8294(6)
_cell_length_c                   16.6986(9)
_cell_measurement_reflns_used    46939
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     2157.32(19)
_computing_cell_refinement
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998)
;
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Version 2.01; Farrugia, 1997) and
Mercury (Version 1.4.2; Macrae <i>et al.</i>, 2006)
;
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla <i>et al.</i>, 2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Bruker Nonius APEXII CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18202
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.9575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.420
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0321P)^2^+3.5864P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1245
_reflns_number_gt                2024
_reflns_number_total             2463
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gg3207.cif
_cod_data_source_block           2b
_cod_original_sg_symbol_Hall     '-P 2n (2a)b'
_cod_original_sg_symbol_H-M      'P bcn'
_cod_database_code               2017512
_cod_database_fobs_code          2017512