#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:48:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201957 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/75/2017513.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_2017513
loop_
_publ_author_name
'Spencer, John'
'Chowdhry, Babur Z.'
'Hamid, Samiyah'
'Mendham, Andrew P.'
'Male, Louise'
'Coles, Simon J.'
'Hursthouse, Michael B.'
_publ_section_title
;
 Seven 3-methylidene-1H-indol-2(3H)-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 O2 , H2 O'
_chemical_formula_moiety         'C13 H9 N O2 , H2 O'
_chemical_formula_sum            'C13 H11 N O3'
_chemical_formula_weight         229.23
_chemical_name_systematic
;
(3E)-3-(2-furylmethylidene)-1H-indol-2(3H)-one
monohydrate
;
_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                   19.2250(7)
_cell_length_b                   5.0503(3)
_cell_length_c                   22.1886(14)
_cell_measurement_reflns_used    8716
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     2154.3(2)
_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 et al., 2006)
;
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0852
_diffrn_reflns_av_sigmaI/netI    0.0636
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13065
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.67
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9959
_exptl_absorpt_correction_T_min  0.9702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.248
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         1881
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0518
_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/[σ²(Fo²)+(0.0432P)²+1.1222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1175
_reflns_number_gt                1355
_reflns_number_total             1881
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg3207.cif
_cod_data_source_block           3a
_cod_original_sg_symbol_Hall     '-P 2n (2a)b'
_cod_original_sg_symbol_H-M      'P bcn'
_cod_database_code               2017513
_cod_database_fobs_code          2017513
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, 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_disorder_assembly
_atom_site_disorder_group
C C1 0.47350(11) -0.1896(5) 0.05249(11) 0.0217(6) Uani d . 1 . .
C C2 0.47019(11) 0.0306(4) 0.09706(11) 0.0204(6) Uani d . 1 . .
C C3 0.53956(11) 0.0371(5) 0.12558(11) 0.0218(6) Uani d . 1 . .
C C4 0.57891(11) -0.1658(5) 0.09850(11) 0.0208(6) Uani d . 1 . .
C C5 0.64777(11) -0.2112(5) 0.11202(11) 0.0237(6) Uani d . 1 . .
H H5 0.6732 -0.3485 0.0928 0.028 Uiso calc R 1 . .
C C6 0.67857(11) -0.0483(5) 0.15485(12) 0.0247(6) Uani d . 1 . .
H H6 0.7261 -0.0738 0.1650 0.030 Uiso calc R 1 . .
C C7 0.64096(12) 0.1510(5) 0.18295(11) 0.0233(6) Uani d . 1 . .
H H7 0.6629 0.2589 0.2124 0.028 Uiso calc R 1 . .
C C8 0.57162(11) 0.1945(5) 0.16843(11) 0.0221(6) Uani d . 1 . .
H H8 0.5463 0.3318 0.1878 0.027 Uiso calc R 1 . .
C C9 0.41034(11) 0.1692(5) 0.10262(11) 0.0226(6) Uani d . 1 . .
H H9 0.3754 0.1164 0.0748 0.027 Uiso calc R 1 . .
C C10 0.38905(11) 0.3767(5) 0.14126(11) 0.0221(6) Uani d . 1 . .
C C11 0.32701(11) 0.5065(5) 0.14502(11) 0.0241(6) Uani d . 1 . .
H H11 0.2874 0.4777 0.1203 0.029 Uiso calc R 1 . .
C C12 0.33264(12) 0.6919(5) 0.19250(12) 0.0262(6) Uani d . 1 . .
H H12 0.2975 0.8103 0.2060 0.031 Uiso calc R 1 . .
C C13 0.39748(12) 0.6683(5) 0.21495(12) 0.0266(6) Uani d . 1 . .
H H13 0.4156 0.7707 0.2473 0.032 Uiso calc R 1 . .
N N1 0.53748(9) -0.2997(4) 0.05613(9) 0.0235(5) Uani d . 1 . .
H H1 0.5513 -0.4368 0.0348 0.028 Uiso calc R 1 . .
O O1 0.42676(8) -0.2639(3) 0.01749(7) 0.0254(4) Uani d . 1 . .
O O2 0.43349(8) 0.4766(3) 0.18474(7) 0.0260(4) Uani d . 1 . .
O O101 0.27917(10) -0.2601(4) 0.00470(12) 0.0518(6) Uani d D 1 . .
H H1W 0.2631(15) -0.100(4) 0.0018(16) 0.078 Uiso d D 1 . .
H H2W 0.3234(9) -0.246(6) 0.0087(16) 0.078 Uiso d D 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 N1 . . 124.7(2) ?
O1 C1 C2 . . 127.4(2) ?
N1 C1 C2 . . 107.8(2) ?
C9 C2 C3 . . 135.9(2) ?
C9 C2 C1 . . 118.9(2) ?
C3 C2 C1 . . 105.23(19) ?
C8 C3 C4 . . 118.2(2) ?
C8 C3 C2 . . 135.2(2) ?
C4 C3 C2 . . 106.6(2) ?
C5 C4 N1 . . 127.6(2) ?
C5 C4 C3 . . 123.0(2) ?
N1 C4 C3 . . 109.33(19) ?
C4 C5 C6 . . 117.4(2) ?
C4 C5 H5 . . 121.3 ?
C6 C5 H5 . . 121.3 ?
C7 C6 C5 . . 121.0(2) ?
C7 C6 H6 . . 119.5 ?
C5 C6 H6 . . 119.5 ?
C6 C7 C8 . . 120.7(2) ?
C6 C7 H7 . . 119.6 ?
C8 C7 H7 . . 119.6 ?
C3 C8 C7 . . 119.7(2) ?
C3 C8 H8 . . 120.1 ?
C7 C8 H8 . . 120.1 ?
C2 C9 C10 . . 133.2(2) ?
C2 C9 H9 . . 113.4 ?
C10 C9 H9 . . 113.4 ?
C11 C10 O2 . . 108.8(2) ?
C11 C10 C9 . . 130.3(2) ?
O2 C10 C9 . . 120.9(2) ?
C10 C11 C12 . . 107.3(2) ?
C10 C11 H11 . . 126.4 ?
C12 C11 H11 . . 126.4 ?
C13 C12 C11 . . 106.7(2) ?
C13 C12 H12 . . 126.6 ?
C11 C12 H12 . . 126.6 ?
C12 C13 O2 . . 110.5(2) ?
C12 C13 H13 . . 124.8 ?
O2 C13 H13 . . 124.8 ?
C1 N1 C4 . . 111.0(2) ?
C1 N1 H1 . . 124.5 ?
C4 N1 H1 . . 124.5 ?
C13 O2 C10 . . 106.72(17) ?
H1W O101 H2W . . 106(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.246(3) ?
C1 N1 . 1.352(3) ?
C1 C2 . 1.489(3) ?
C2 C9 . 1.353(3) ?
C2 C3 . 1.477(3) ?
C3 C8 . 1.384(3) ?
C3 C4 . 1.408(3) ?
C4 C5 . 1.377(3) ?
C4 N1 . 1.406(3) ?
C5 C6 . 1.389(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.387(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.389(3) ?
C7 H7 . 0.9500 ?
C8 H8 . 0.9500 ?
C9 C10 . 1.414(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.364(3) ?
C10 O2 . 1.384(3) ?
C11 C12 . 1.414(4) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.348(3) ?
C12 H12 . 0.9500 ?
C13 O2 . 1.366(3) ?
C13 H13 . 0.9500 ?
N1 H1 . 0.8800 ?
O101 H1W . 0.870(18) ?
O101 H2W . 0.858(17) ?
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
_geom_hbond_publ_flag
N1 H1 O1 5_645 0.88 1.95 2.828(3) 174.0 no
O101 H1W O101 7_665 0.870(18) 1.899(18) 2.7630(15) 172(3) no
O101 H2W O1 . 0.858(17) 1.999(17) 2.852(2) 173(3) no
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C9 . . . . 1.2(4) ?
N1 C1 C2 C9 . . . . -178.9(2) ?
O1 C1 C2 C3 . . . . -178.9(2) ?
N1 C1 C2 C3 . . . . 1.1(2) ?
C9 C2 C3 C8 . . . . -2.4(5) ?
C1 C2 C3 C8 . . . . 177.7(3) ?
C9 C2 C3 C4 . . . . -179.9(3) ?
C1 C2 C3 C4 . . . . 0.1(2) ?
C8 C3 C4 C5 . . . . -1.1(4) ?
C2 C3 C4 C5 . . . . 177.0(2) ?
C8 C3 C4 N1 . . . . -179.3(2) ?
C2 C3 C4 N1 . . . . -1.3(3) ?
N1 C4 C5 C6 . . . . 178.5(2) ?
C3 C4 C5 C6 . . . . 0.6(4) ?
C4 C5 C6 C7 . . . . 0.3(4) ?
C5 C6 C7 C8 . . . . -0.7(4) ?
C4 C3 C8 C7 . . . . 0.7(3) ?
C2 C3 C8 C7 . . . . -176.7(2) ?
C6 C7 C8 C3 . . . . 0.2(3) ?
C3 C2 C9 C10 . . . . -3.1(5) ?
C1 C2 C9 C10 . . . . 176.8(2) ?
C2 C9 C10 C11 . . . . -179.0(3) ?
C2 C9 C10 O2 . . . . -0.4(4) ?
O2 C10 C11 C12 . . . . -0.4(3) ?
C9 C10 C11 C12 . . . . 178.4(2) ?
C10 C11 C12 C13 . . . . 0.5(3) ?
C11 C12 C13 O2 . . . . -0.4(3) ?
O1 C1 N1 C4 . . . . 178.1(2) ?
C2 C1 N1 C4 . . . . -1.9(3) ?
C5 C4 N1 C1 . . . . -176.1(2) ?
C3 C4 N1 C1 . . . . 2.0(3) ?
C12 C13 O2 C10 . . . . 0.2(3) ?
C11 C10 O2 C13 . . . . 0.1(3) ?
C9 C10 O2 C13 . . . . -178.8(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654215
