#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/75/2017514.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_2017514
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          'C11 H11 N O'
_chemical_formula_moiety         'C11 H11 N O'
_chemical_formula_sum            'C11 H11 N O'
_chemical_formula_weight         173.21
_chemical_name_systematic
;
3-(1-methylethylidene)-1H-indol-2(3H)-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                95.766(2)
_cell_angle_beta                 107.842(2)
_cell_angle_gamma                96.617(2)
_cell_formula_units_Z            6
_cell_length_a                   9.7504(3)
_cell_length_b                   10.2281(3)
_cell_length_c                   14.0530(5)
_cell_measurement_reflns_used    16164
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1311.46(8)
_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 '4096x4096pixels / 62x62mm'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
'Bruker Nonius APEXII CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ and ω 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  0.0592
_diffrn_reflns_av_sigmaI/netI    0.0674
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21390
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9966
_exptl_absorpt_correction_T_min  0.9750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            'light orange'
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.312
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         5972
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0788
_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)+(0.0214P)²+2.3372P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.1681
_reflns_number_gt                4122
_reflns_number_total             5972
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg3207.cif
_cod_data_source_block           4a
_cod_original_cell_volume        1311.45(7)
_cod_database_code               2017514
_cod_database_fobs_code          2017514
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.9147(3) 0.0015(2) 0.3484(2) 0.0191(5) Uani d . 1 . .
C C2 0.8145(3) 0.0030(2) 0.24248(19) 0.0185(5) Uani d . 1 . .
C C3 0.6692(3) 0.0080(2) 0.25253(19) 0.0185(5) Uani d . 1 . .
C C4 0.6851(3) 0.0091(2) 0.3554(2) 0.0198(6) Uani d . 1 . .
C C5 0.5695(3) 0.0098(3) 0.3926(2) 0.0250(6) Uani d . 1 . .
H H5 0.5836 0.0113 0.4626 0.030 Uiso calc R 1 . .
C C6 0.4314(3) 0.0084(3) 0.3239(2) 0.0277(6) Uani d . 1 . .
H H6 0.3497 0.0088 0.3471 0.033 Uiso calc R 1 . .
C C7 0.4125(3) 0.0065(3) 0.2220(2) 0.0266(6) Uani d . 1 . .
H H7 0.3175 0.0049 0.1762 0.032 Uiso calc R 1 . .
C C8 0.5304(3) 0.0068(3) 0.1855(2) 0.0240(6) Uani d . 1 . .
H H8 0.5159 0.0062 0.1154 0.029 Uiso calc R 1 . .
C C9 0.8559(3) 0.0002(2) 0.1591(2) 0.0214(6) Uani d . 1 . .
C C10 0.7509(3) 0.0086(3) 0.0571(2) 0.0263(6) Uani d . 1 . .
H H10A 0.6692 -0.0646 0.0396 0.040 Uiso calc R 1 . .
H H10B 0.8008 0.0021 0.0064 0.040 Uiso calc R 1 . .
H H10C 0.7140 0.0936 0.0587 0.040 Uiso calc R 1 . .
C C11 1.0083(3) -0.0114(3) 0.1595(2) 0.0293(7) Uani d . 1 . .
H H11A 1.0706 -0.0132 0.2288 0.044 Uiso calc R 1 . .
H H11B 1.0465 0.0650 0.1333 0.044 Uiso calc R 1 . .
H H11C 1.0072 -0.0937 0.1168 0.044 Uiso calc R 1 . .
N N1 0.8302(2) 0.0067(2) 0.40969(17) 0.0210(5) Uani d . 1 . .
H H1 0.8635 0.0083 0.4756 0.025 Uiso calc R 1 . .
O O1 1.0469(2) -0.00082(18) 0.37839(14) 0.0229(4) Uani d . 1 . .
C C101 1.1804(3) 0.3134(2) 0.67501(19) 0.0190(5) Uani d . 1 . .
C C102 1.0822(3) 0.3172(2) 0.5693(2) 0.0193(5) Uani d . 1 . .
C C103 0.9363(3) 0.3213(2) 0.57864(19) 0.0192(6) Uani d . 1 . .
C C104 0.9502(3) 0.3190(2) 0.6811(2) 0.0212(6) Uani d . 1 . .
C C105 0.8340(3) 0.3202(3) 0.7174(2) 0.0257(6) Uani d . 1 . .
H H105 0.8472 0.3190 0.7871 0.031 Uiso calc R 1 . .
C C106 0.6973(3) 0.3231(3) 0.6493(2) 0.0280(6) Uani d . 1 . .
H H106 0.6155 0.3240 0.6724 0.034 Uiso calc R 1 . .
C C107 0.6796(3) 0.3249(3) 0.5477(2) 0.0291(6) Uani d . 1 . .
H H107 0.5854 0.3269 0.5019 0.035 Uiso calc R 1 . .
C C108 0.7983(3) 0.3238(3) 0.5115(2) 0.0268(6) Uani d . 1 . .
H H108 0.7848 0.3247 0.4417 0.032 Uiso calc R 1 . .
C C109 1.1276(3) 0.3190(2) 0.4874(2) 0.0213(6) Uani d . 1 . .
C C110 1.0276(3) 0.3347(3) 0.3856(2) 0.0314(7) Uani d . 1 . .
H H11D 0.9703 0.2482 0.3516 0.047 Uiso calc R 1 . .
H H11E 1.0855 0.3687 0.3448 0.047 Uiso calc R 1 . .
H H11F 0.9618 0.3973 0.3937 0.047 Uiso calc R 1 . .
C C111 1.2798(3) 0.3054(3) 0.4896(2) 0.0290(7) Uani d . 1 . .
H H11G 1.3339 0.2812 0.5549 0.043 Uiso calc R 1 . .
H H11H 1.3284 0.3901 0.4802 0.043 Uiso calc R 1 . .
H H11I 1.2766 0.2360 0.4353 0.043 Uiso calc R 1 . .
N N101 1.0952(2) 0.3153(2) 0.73532(17) 0.0216(5) Uani d . 1 . .
H H101 1.1277 0.3143 0.8009 0.026 Uiso calc R 1 . .
O O101 1.3130(2) 0.31170(18) 0.70609(14) 0.0242(4) Uani d . 1 . .
C C201 1.3470(3) 0.3250(2) 0.9789(2) 0.0202(6) Uani d . 1 . .
C C202 1.4479(3) 0.3417(2) 1.0863(2) 0.0194(5) Uani d . 1 . .
C C203 1.5959(3) 0.3479(2) 1.0787(2) 0.0200(6) Uani d . 1 . .
C C204 1.5804(3) 0.3330(2) 0.9751(2) 0.0202(6) Uani d . 1 . .
C C205 1.6974(3) 0.3345(3) 0.9397(2) 0.0243(6) Uani d . 1 . .
H H205 1.6835 0.3230 0.8693 0.029 Uiso calc R 1 . .
C C206 1.8367(3) 0.3533(3) 1.0099(2) 0.0258(6) Uani d . 1 . .
H H206 1.9194 0.3558 0.9875 0.031 Uiso calc R 1 . .
C C207 1.8552(3) 0.3686(3) 1.1127(2) 0.0279(6) Uani d . 1 . .
H H207 1.9509 0.3813 1.1598 0.033 Uiso calc R 1 . .
C C208 1.7363(3) 0.3658(3) 1.1479(2) 0.0246(6) Uani d . 1 . .
H H208 1.7506 0.3759 1.2183 0.030 Uiso calc R 1 . .
C C209 1.4052(3) 0.3485(2) 1.1693(2) 0.0204(6) Uani d . 1 . .
C C210 1.5128(3) 0.3655(3) 1.2744(2) 0.0283(6) Uani d . 1 . .
H H21A 1.5684 0.2911 1.2811 0.043 Uiso calc R 1 . .
H H21B 1.4603 0.3674 1.3237 0.043 Uiso calc R 1 . .
H H21C 1.5797 0.4492 1.2867 0.043 Uiso calc R 1 . .
C C211 1.2486(3) 0.3408(3) 1.1650(2) 0.0288(6) Uani d . 1 . .
H H21D 1.1857 0.3261 1.0944 0.043 Uiso calc R 1 . .
H H21E 1.2346 0.4243 1.1990 0.043 Uiso calc R 1 . .
H H21F 1.2232 0.2670 1.1990 0.043 Uiso calc R 1 . .
N N201 1.4328(2) 0.3184(2) 0.91886(17) 0.0212(5) Uani d . 1 . .
H H201 1.3992 0.3063 0.8524 0.025 Uiso calc R 1 . .
O O201 1.2127(2) 0.31515(18) 0.94666(14) 0.0236(4) Uani 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 . . 124.2(2) ?
O1 C1 C2 . . 129.4(2) ?
N1 C1 C2 . . 106.4(2) ?
C9 C2 C3 . . 129.6(2) ?
C9 C2 C1 . . 125.2(2) ?
C3 C2 C1 . . 105.3(2) ?
C8 C3 C4 . . 118.2(2) ?
C8 C3 C2 . . 134.9(2) ?
C4 C3 C2 . . 106.8(2) ?
C5 C4 N1 . . 127.3(2) ?
C5 C4 C3 . . 123.0(3) ?
N1 C4 C3 . . 109.8(2) ?
C4 C5 C6 . . 117.7(3) ?
C4 C5 H5 . . 121.1 ?
C6 C5 H5 . . 121.1 ?
C7 C6 C5 . . 120.5(3) ?
C7 C6 H6 . . 119.8 ?
C5 C6 H6 . . 119.8 ?
C6 C7 C8 . . 121.2(3) ?
C6 C7 H7 . . 119.4 ?
C8 C7 H7 . . 119.4 ?
C3 C8 C7 . . 119.4(3) ?
C3 C8 H8 . . 120.3 ?
C7 C8 H8 . . 120.3 ?
C2 C9 C11 . . 123.7(3) ?
C2 C9 C10 . . 121.9(3) ?
C11 C9 C10 . . 114.4(2) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C9 C11 H11A . . 109.5 ?
C9 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C9 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C1 N1 C4 . . 111.7(2) ?
C1 N1 H1 . . 124.1 ?
C4 N1 H1 . . 124.1 ?
O101 C101 N101 . . 123.8(2) ?
O101 C101 C102 . . 129.5(2) ?
N101 C101 C102 . . 106.7(2) ?
C109 C102 C103 . . 130.4(3) ?
C109 C102 C101 . . 124.5(2) ?
C103 C102 C101 . . 105.1(2) ?
C108 C103 C104 . . 118.0(2) ?
C108 C103 C102 . . 135.0(2) ?
C104 C103 C102 . . 107.0(2) ?
C105 C104 N101 . . 127.7(3) ?
C105 C104 C103 . . 123.0(3) ?
N101 C104 C103 . . 109.3(2) ?
C104 C105 C106 . . 118.2(3) ?
C104 C105 H105 . . 120.9 ?
C106 C105 H105 . . 120.9 ?
C107 C106 C105 . . 120.4(3) ?
C107 C106 H106 . . 119.8 ?
C105 C106 H106 . . 119.8 ?
C106 C107 C108 . . 121.0(3) ?
C106 C107 H107 . . 119.5 ?
C108 C107 H107 . . 119.5 ?
C103 C108 C107 . . 119.4(3) ?
C103 C108 H108 . . 120.3 ?
C107 C108 H108 . . 120.3 ?
C102 C109 C111 . . 123.7(3) ?
C102 C109 C110 . . 122.2(3) ?
C111 C109 C110 . . 114.1(2) ?
C109 C110 H11D . . 109.5 ?
C109 C110 H11E . . 109.5 ?
H11D C110 H11E . . 109.5 ?
C109 C110 H11F . . 109.5 ?
H11D C110 H11F . . 109.5 ?
H11E C110 H11F . . 109.5 ?
C109 C111 H11G . . 109.5 ?
C109 C111 H11H . . 109.5 ?
H11G C111 H11H . . 109.5 ?
C109 C111 H11I . . 109.5 ?
H11G C111 H11I . . 109.5 ?
H11H C111 H11I . . 109.5 ?
C101 N101 C104 . . 112.0(2) ?
C101 N101 H101 . . 124.0 ?
C104 N101 H101 . . 124.0 ?
O201 C201 N201 . . 124.0(2) ?
O201 C201 C202 . . 129.6(2) ?
N201 C201 C202 . . 106.4(2) ?
C209 C202 C203 . . 129.5(3) ?
C209 C202 C201 . . 125.1(2) ?
C203 C202 C201 . . 105.4(2) ?
C208 C203 C204 . . 118.2(2) ?
C208 C203 C202 . . 135.0(2) ?
C204 C203 C202 . . 106.8(2) ?
C205 C204 N201 . . 127.9(2) ?
C205 C204 C203 . . 122.8(3) ?
N201 C204 C203 . . 109.3(2) ?
C204 C205 C206 . . 118.2(3) ?
C204 C205 H205 . . 120.9 ?
C206 C205 H205 . . 120.9 ?
C207 C206 C205 . . 120.2(3) ?
C207 C206 H206 . . 119.9 ?
C205 C206 H206 . . 119.9 ?
C206 C207 C208 . . 121.3(3) ?
C206 C207 H207 . . 119.4 ?
C208 C207 H207 . . 119.4 ?
C207 C208 C203 . . 119.4(3) ?
C207 C208 H208 . . 120.3 ?
C203 C208 H208 . . 120.3 ?
C202 C209 C211 . . 123.4(3) ?
C202 C209 C210 . . 122.0(3) ?
C211 C209 C210 . . 114.6(2) ?
C209 C210 H21A . . 109.5 ?
C209 C210 H21B . . 109.5 ?
H21A C210 H21B . . 109.5 ?
C209 C210 H21C . . 109.5 ?
H21A C210 H21C . . 109.5 ?
H21B C210 H21C . . 109.5 ?
C209 C211 H21D . . 109.5 ?
C209 C211 H21E . . 109.5 ?
H21D C211 H21E . . 109.5 ?
C209 C211 H21F . . 109.5 ?
H21D C211 H21F . . 109.5 ?
H21E C211 H21F . . 109.5 ?
C201 N201 C204 . . 112.0(2) ?
C201 N201 H201 . . 124.0 ?
C204 N201 H201 . . 124.0 ?
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 . 1.232(3) ?
C1 N1 . 1.363(3) ?
C1 C2 . 1.512(4) ?
C2 C9 . 1.351(4) ?
C2 C3 . 1.472(4) ?
C3 C8 . 1.390(4) ?
C3 C4 . 1.404(3) ?
C4 C5 . 1.381(4) ?
C4 N1 . 1.391(3) ?
C5 C6 . 1.393(4) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.384(4) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.395(4) ?
C7 H7 . 0.9500 ?
C8 H8 . 0.9500 ?
C9 C11 . 1.502(4) ?
C9 C10 . 1.502(4) ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
N1 H1 . 0.8800 ?
C101 O101 . 1.234(3) ?
C101 N101 . 1.357(3) ?
C101 C102 . 1.508(4) ?
C102 C109 . 1.355(4) ?
C102 C103 . 1.473(4) ?
C103 C108 . 1.391(4) ?
C103 C104 . 1.407(4) ?
C104 C105 . 1.378(4) ?
C104 N101 . 1.393(3) ?
C105 C106 . 1.388(4) ?
C105 H105 . 0.9500 ?
C106 C107 . 1.386(4) ?
C106 H106 . 0.9500 ?
C107 C108 . 1.401(4) ?
C107 H107 . 0.9500 ?
C108 H108 . 0.9500 ?
C109 C111 . 1.497(4) ?
C109 C110 . 1.500(4) ?
C110 H11D . 0.9800 ?
C110 H11E . 0.9800 ?
C110 H11F . 0.9800 ?
C111 H11G . 0.9800 ?
C111 H11H . 0.9800 ?
C111 H11I . 0.9800 ?
N101 H101 . 0.8800 ?
C201 O201 . 1.235(3) ?
C201 N201 . 1.360(3) ?
C201 C202 . 1.509(4) ?
C202 C209 . 1.351(4) ?
C202 C203 . 1.474(4) ?
C203 C208 . 1.394(4) ?
C203 C204 . 1.408(4) ?
C204 C205 . 1.376(4) ?
C204 N201 . 1.396(3) ?
C205 C206 . 1.390(4) ?
C205 H205 . 0.9500 ?
C206 C207 . 1.390(4) ?
C206 H206 . 0.9500 ?
C207 C208 . 1.391(4) ?
C207 H207 . 0.9500 ?
C208 H208 . 0.9500 ?
C209 C211 . 1.502(4) ?
C209 C210 . 1.507(4) ?
C210 H21A . 0.9800 ?
C210 H21B . 0.9800 ?
C210 H21C . 0.9800 ?
C211 H21D . 0.9800 ?
C211 H21E . 0.9800 ?
C211 H21F . 0.9800 ?
N201 H201 . 0.8800 ?
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 2_756 0.88 1.98 2.859(3) 174.2 no
N101 H101 O201 . 0.88 1.96 2.837(3) 176.3 no
N201 H201 O101 . 0.88 1.98 2.848(3) 169.5 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 . . . . 0.9(4) ?
N1 C1 C2 C9 . . . . 179.4(2) ?
O1 C1 C2 C3 . . . . -179.1(2) ?
N1 C1 C2 C3 . . . . -0.6(3) ?
C9 C2 C3 C8 . . . . 2.8(5) ?
C1 C2 C3 C8 . . . . -177.3(3) ?
C9 C2 C3 C4 . . . . 180.0(3) ?
C1 C2 C3 C4 . . . . -0.1(3) ?
C8 C3 C4 C5 . . . . -0.5(4) ?
C2 C3 C4 C5 . . . . -178.2(2) ?
C8 C3 C4 N1 . . . . 178.4(2) ?
C2 C3 C4 N1 . . . . 0.7(3) ?
N1 C4 C5 C6 . . . . -178.2(3) ?
C3 C4 C5 C6 . . . . 0.5(4) ?
C4 C5 C6 C7 . . . . -0.1(4) ?
C5 C6 C7 C8 . . . . -0.4(4) ?
C4 C3 C8 C7 . . . . -0.1(4) ?
C2 C3 C8 C7 . . . . 176.8(3) ?
C6 C7 C8 C3 . . . . 0.5(4) ?
C3 C2 C9 C11 . . . . -177.0(3) ?
C1 C2 C9 C11 . . . . 3.1(4) ?
C3 C2 C9 C10 . . . . 2.9(4) ?
C1 C2 C9 C10 . . . . -177.0(2) ?
O1 C1 N1 C4 . . . . 179.7(2) ?
C2 C1 N1 C4 . . . . 1.0(3) ?
C5 C4 N1 C1 . . . . 177.7(3) ?
C3 C4 N1 C1 . . . . -1.2(3) ?
O101 C101 C102 C109 . . . . 0.3(4) ?
N101 C101 C102 C109 . . . . 178.8(2) ?
O101 C101 C102 C103 . . . . -178.5(2) ?
N101 C101 C102 C103 . . . . 0.0(3) ?
C109 C102 C103 C108 . . . . 2.5(5) ?
C101 C102 C103 C108 . . . . -178.8(3) ?
C109 C102 C103 C104 . . . . -179.1(3) ?
C101 C102 C103 C104 . . . . -0.4(3) ?
C108 C103 C104 C105 . . . . -0.5(4) ?
C102 C103 C104 C105 . . . . -179.2(2) ?
C108 C103 C104 N101 . . . . 179.3(2) ?
C102 C103 C104 N101 . . . . 0.6(3) ?
N101 C104 C105 C106 . . . . -179.6(3) ?
C103 C104 C105 C106 . . . . 0.3(4) ?
C104 C105 C106 C107 . . . . 0.0(4) ?
C105 C106 C107 C108 . . . . 0.0(4) ?
C104 C103 C108 C107 . . . . 0.5(4) ?
C102 C103 C108 C107 . . . . 178.7(3) ?
C106 C107 C108 C103 . . . . -0.2(4) ?
C103 C102 C109 C111 . . . . -175.9(3) ?
C101 C102 C109 C111 . . . . 5.6(4) ?
C103 C102 C109 C110 . . . . 3.9(4) ?
C101 C102 C109 C110 . . . . -174.6(2) ?
O101 C101 N101 C104 . . . . 179.1(2) ?
C102 C101 N101 C104 . . . . 0.4(3) ?
C105 C104 N101 C101 . . . . 179.2(3) ?
C103 C104 N101 C101 . . . . -0.7(3) ?
O201 C201 C202 C209 . . . . 0.2(4) ?
N201 C201 C202 C209 . . . . -178.0(2) ?
O201 C201 C202 C203 . . . . -179.9(3) ?
N201 C201 C202 C203 . . . . 1.9(3) ?
C209 C202 C203 C208 . . . . -2.2(5) ?
C201 C202 C203 C208 . . . . 177.9(3) ?
C209 C202 C203 C204 . . . . 178.6(3) ?
C201 C202 C203 C204 . . . . -1.2(3) ?
C208 C203 C204 C205 . . . . 0.4(4) ?
C202 C203 C204 C205 . . . . 179.7(2) ?
C208 C203 C204 N201 . . . . -179.2(2) ?
C202 C203 C204 N201 . . . . 0.2(3) ?
N201 C204 C205 C206 . . . . 178.6(2) ?
C203 C204 C205 C206 . . . . -0.8(4) ?
C204 C205 C206 C207 . . . . 0.7(4) ?
C205 C206 C207 C208 . . . . -0.1(4) ?
C206 C207 C208 C203 . . . . -0.3(4) ?
C204 C203 C208 C207 . . . . 0.2(4) ?
C202 C203 C208 C207 . . . . -178.9(3) ?
C203 C202 C209 C211 . . . . 179.9(2) ?
C201 C202 C209 C211 . . . . -0.3(4) ?
C203 C202 C209 C210 . . . . 0.3(4) ?
C201 C202 C209 C210 . . . . -179.8(2) ?
O201 C201 N201 C204 . . . . 179.8(2) ?
C202 C201 N201 C204 . . . . -1.9(3) ?
C205 C204 N201 C201 . . . . -178.4(3) ?
C203 C204 N201 C201 . . . . 1.1(3) ?
