#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/75/2017516.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_2017516
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          'C14 H15 N O'
_chemical_formula_moiety         'C14 H15 N O'
_chemical_formula_sum            'C14 H15 N O'
_chemical_formula_weight         213.27
_chemical_name_systematic
;
3-cyclohexylidene-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                95.3890(10)
_cell_angle_beta                 98.498(2)
_cell_angle_gamma                101.201(2)
_cell_formula_units_Z            4
_cell_length_a                   5.37320(10)
_cell_length_b                   13.4962(4)
_cell_length_c                   15.8088(5)
_cell_measurement_reflns_used    12338
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1103.32(5)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18503
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_correction_T_min  0.9346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.85
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.235
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4997
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0660
_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)+(0.0002P)²+1.4948P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1347
_reflns_number_gt                3778
_reflns_number_total             4997
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg3207.cif
_cod_data_source_block           4c
_cod_database_code               2017516
_cod_database_fobs_code          2017516
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 1.2267(4) 0.49598(18) 0.07719(13) 0.0215(5) Uani d . 1 . .
C C2 1.0170(4) 0.46698(17) 0.12946(13) 0.0197(4) Uani d . 1 . .
C C3 0.9590(4) 0.35410(17) 0.11870(14) 0.0215(5) Uani d . 1 . .
C C4 1.1289(4) 0.32256(17) 0.06723(14) 0.0219(5) Uani d . 1 . .
C C5 1.1335(5) 0.22196(18) 0.04454(15) 0.0265(5) Uani d . 1 . .
H H5 1.2530 0.2034 0.0105 0.032 Uiso calc R 1 . .
C C6 0.9566(5) 0.14822(18) 0.07327(15) 0.0273(5) Uani d . 1 . .
H H6 0.9559 0.0782 0.0592 0.033 Uiso calc R 1 . .
C C7 0.7826(5) 0.17608(18) 0.12201(15) 0.0274(5) Uani d . 1 . .
H H7 0.6623 0.1249 0.1407 0.033 Uiso calc R 1 . .
C C8 0.7811(4) 0.27834(18) 0.14421(15) 0.0256(5) Uani d . 1 . .
H H8 0.6581 0.2964 0.1769 0.031 Uiso calc R 1 . .
C C9 0.9254(4) 0.53507(17) 0.17809(14) 0.0218(5) Uani d . 1 . .
C C10 0.7413(5) 0.50503(19) 0.23890(16) 0.0296(5) Uani d . 1 . .
H H10A 0.6947 0.4299 0.2350 0.035 Uiso calc R 1 . .
H H10B 0.5817 0.5301 0.2224 0.035 Uiso calc R 1 . .
C C11 0.8652(5) 0.55019(18) 0.33175(15) 0.0264(5) Uani d . 1 . .
H H11A 0.7406 0.5318 0.3709 0.032 Uiso calc R 1 . .
H H11B 1.0173 0.5210 0.3496 0.032 Uiso calc R 1 . .
C C12 0.9474(4) 0.66549(17) 0.33919(15) 0.0242(5) Uani d . 1 . .
H H12A 1.0360 0.6926 0.3987 0.029 Uiso calc R 1 . .
H H12B 0.7933 0.6953 0.3272 0.029 Uiso calc R 1 . .
C C13 1.1275(4) 0.69620(17) 0.27574(15) 0.0243(5) Uani d . 1 . .
H H13A 1.2907 0.6738 0.2924 0.029 Uiso calc R 1 . .
H H13B 1.1681 0.7713 0.2785 0.029 Uiso calc R 1 . .
C C14 1.0064(4) 0.64885(17) 0.18258(15) 0.0241(5) Uani d . 1 . .
H H14A 0.8548 0.6776 0.1631 0.029 Uiso calc R 1 . .
H H14B 1.1329 0.6658 0.1438 0.029 Uiso calc R 1 . .
N N1 1.2855(4) 0.40804(14) 0.04460(12) 0.0234(4) Uani d . 1 . .
H H1 1.4069 0.4053 0.0132 0.028 Uiso calc R 1 . .
O O1 1.3379(3) 0.58122(12) 0.06518(10) 0.0255(4) Uani d . 1 . .
C C101 0.7052(4) 0.05891(16) 0.44320(15) 0.0208(5) Uani d . 1 . .
C C102 0.4930(4) 0.08886(16) 0.38401(14) 0.0202(5) Uani d . 1 . .
C C103 0.4658(4) 0.02215(16) 0.30140(14) 0.0211(5) Uani d . 1 . .
C C104 0.6567(4) -0.03585(16) 0.31196(15) 0.0220(5) Uani d . 1 . .
C C105 0.6866(5) -0.10715(18) 0.24781(16) 0.0271(5) Uani d . 1 . .
H H105 0.8198 -0.1441 0.2564 0.033 Uiso calc R 1 . .
C C106 0.5157(5) -0.12313(18) 0.17030(16) 0.0295(5) Uani d . 1 . .
H H106 0.5331 -0.1710 0.1247 0.035 Uiso calc R 1 . .
C C107 0.3196(5) -0.06953(18) 0.15912(15) 0.0281(5) Uani d . 1 . .
H H107 0.2018 -0.0823 0.1063 0.034 Uiso calc R 1 . .
C C108 0.2931(4) 0.00282(17) 0.22444(15) 0.0246(5) Uani d . 1 . .
H H108 0.1575 0.0386 0.2162 0.030 Uiso calc R 1 . .
C C109 0.3749(4) 0.16534(16) 0.40503(14) 0.0211(5) Uani d . 1 . .
C C110 0.1966(5) 0.20541(17) 0.33968(15) 0.0269(5) Uani d . 1 . .
H H11C 0.0179 0.1862 0.3507 0.032 Uiso calc R 1 . .
H H11D 0.2016 0.1738 0.2810 0.032 Uiso calc R 1 . .
C C111 0.2739(5) 0.32120(17) 0.34438(15) 0.0269(5) Uani d . 1 . .
H H11E 0.4421 0.3396 0.3250 0.032 Uiso calc R 1 . .
H H11F 0.1448 0.3456 0.3048 0.032 Uiso calc R 1 . .
C C112 0.2938(5) 0.37387(17) 0.43536(15) 0.0263(5) Uani d . 1 . .
H H11G 0.1226 0.3604 0.4532 0.032 Uiso calc R 1 . .
H H11H 0.3508 0.4484 0.4365 0.032 Uiso calc R 1 . .
C C113 0.4856(4) 0.33473(17) 0.49802(15) 0.0239(5) Uani d . 1 . .
H H11I 0.4918 0.3673 0.5573 0.029 Uiso calc R 1 . .
H H11J 0.6596 0.3534 0.4829 0.029 Uiso calc R 1 . .
C C114 0.4086(4) 0.21904(17) 0.49482(14) 0.0225(5) Uani d . 1 . .
H H11K 0.5428 0.1951 0.5326 0.027 Uiso calc R 1 . .
H H11L 0.2454 0.2014 0.5174 0.027 Uiso calc R 1 . .
N N101 0.7970(3) -0.01058(14) 0.39543(12) 0.0236(4) Uani d . 1 . .
H H101 0.9293 -0.0365 0.4148 0.028 Uiso calc R 1 . .
O O101 0.7941(3) 0.09076(12) 0.51969(10) 0.0255(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 . . 123.3(2) ?
O1 C1 C2 . . 129.5(2) ?
N1 C1 C2 . . 107.13(18) ?
C9 C2 C3 . . 131.1(2) ?
C9 C2 C1 . . 124.0(2) ?
C3 C2 C1 . . 104.83(18) ?
C8 C3 C4 . . 117.2(2) ?
C8 C3 C2 . . 135.8(2) ?
C4 C3 C2 . . 106.95(19) ?
C5 C4 N1 . . 127.1(2) ?
C5 C4 C3 . . 123.4(2) ?
N1 C4 C3 . . 109.48(19) ?
C4 C5 C6 . . 117.6(2) ?
C4 C5 H5 . . 121.2 ?
C6 C5 H5 . . 121.2 ?
C7 C6 C5 . . 120.6(2) ?
C7 C6 H6 . . 119.7 ?
C5 C6 H6 . . 119.7 ?
C6 C7 C8 . . 120.8(2) ?
C6 C7 H7 . . 119.6 ?
C8 C7 H7 . . 119.6 ?
C3 C8 C7 . . 120.3(2) ?
C3 C8 H8 . . 119.9 ?
C7 C8 H8 . . 119.9 ?
C2 C9 C14 . . 124.7(2) ?
C2 C9 C10 . . 123.3(2) ?
C14 C9 C10 . . 111.85(19) ?
C9 C10 C11 . . 110.14(19) ?
C9 C10 H10A . . 109.6 ?
C11 C10 H10A . . 109.6 ?
C9 C10 H10B . . 109.6 ?
C11 C10 H10B . . 109.6 ?
H10A C10 H10B . . 108.1 ?
C12 C11 C10 . . 110.90(19) ?
C12 C11 H11A . . 109.5 ?
C10 C11 H11A . . 109.5 ?
C12 C11 H11B . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 108.0 ?
C11 C12 C13 . . 110.63(19) ?
C11 C12 H12A . . 109.5 ?
C13 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
C13 C12 H12B . . 109.5 ?
H12A C12 H12B . . 108.1 ?
C12 C13 C14 . . 111.61(19) ?
C12 C13 H13A . . 109.3 ?
C14 C13 H13A . . 109.3 ?
C12 C13 H13B . . 109.3 ?
C14 C13 H13B . . 109.3 ?
H13A C13 H13B . . 108.0 ?
C9 C14 C13 . . 110.24(18) ?
C9 C14 H14A . . 109.6 ?
C13 C14 H14A . . 109.6 ?
C9 C14 H14B . . 109.6 ?
C13 C14 H14B . . 109.6 ?
H14A C14 H14B . . 108.1 ?
C1 N1 C4 . . 111.54(18) ?
C1 N1 H1 . . 124.2 ?
C4 N1 H1 . . 124.2 ?
O101 C101 N101 . . 123.7(2) ?
O101 C101 C102 . . 129.4(2) ?
N101 C101 C102 . . 106.85(19) ?
C109 C102 C103 . . 130.7(2) ?
C109 C102 C101 . . 124.5(2) ?
C103 C102 C101 . . 104.66(18) ?
C108 C103 C104 . . 118.1(2) ?
C108 C103 C102 . . 134.7(2) ?
C104 C103 C102 . . 107.06(19) ?
C105 C104 N101 . . 127.8(2) ?
C105 C104 C103 . . 122.9(2) ?
N101 C104 C103 . . 109.2(2) ?
C104 C105 C106 . . 117.9(2) ?
C104 C105 H105 . . 121.1 ?
C106 C105 H105 . . 121.1 ?
C107 C106 C105 . . 120.4(2) ?
C107 C106 H106 . . 119.8 ?
C105 C106 H106 . . 119.8 ?
C106 C107 C108 . . 120.9(2) ?
C106 C107 H107 . . 119.5 ?
C108 C107 H107 . . 119.5 ?
C103 C108 C107 . . 119.7(2) ?
C103 C108 H108 . . 120.2 ?
C107 C108 H108 . . 120.2 ?
C102 C109 C114 . . 123.5(2) ?
C102 C109 C110 . . 123.0(2) ?
C114 C109 C110 . . 113.48(19) ?
C109 C110 C111 . . 111.26(19) ?
C109 C110 H11C . . 109.4 ?
C111 C110 H11C . . 109.4 ?
C109 C110 H11D . . 109.4 ?
C111 C110 H11D . . 109.4 ?
H11C C110 H11D . . 108.0 ?
C112 C111 C110 . . 111.86(19) ?
C112 C111 H11E . . 109.2 ?
C110 C111 H11E . . 109.2 ?
C112 C111 H11F . . 109.2 ?
C110 C111 H11F . . 109.2 ?
H11E C111 H11F . . 107.9 ?
C111 C112 C113 . . 110.08(19) ?
C111 C112 H11G . . 109.6 ?
C113 C112 H11G . . 109.6 ?
C111 C112 H11H . . 109.6 ?
C113 C112 H11H . . 109.6 ?
H11G C112 H11H . . 108.2 ?
C112 C113 C114 . . 110.81(19) ?
C112 C113 H11I . . 109.5 ?
C114 C113 H11I . . 109.5 ?
C112 C113 H11J . . 109.5 ?
C114 C113 H11J . . 109.5 ?
H11I C113 H11J . . 108.1 ?
C109 C114 C113 . . 112.15(18) ?
C109 C114 H11K . . 109.2 ?
C113 C114 H11K . . 109.2 ?
C109 C114 H11L . . 109.2 ?
C113 C114 H11L . . 109.2 ?
H11K C114 H11L . . 107.9 ?
C101 N101 C104 . . 111.99(18) ?
C101 N101 H101 . . 124.0 ?
C104 N101 H101 . . 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 . 1.234(3) ?
C1 N1 . 1.361(3) ?
C1 C2 . 1.507(3) ?
C2 C9 . 1.354(3) ?
C2 C3 . 1.483(3) ?
C3 C8 . 1.390(3) ?
C3 C4 . 1.408(3) ?
C4 C5 . 1.377(3) ?
C4 N1 . 1.399(3) ?
C5 C6 . 1.395(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.380(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.393(3) ?
C7 H7 . 0.9500 ?
C8 H8 . 0.9500 ?
C9 C14 . 1.504(3) ?
C9 C10 . 1.505(3) ?
C10 C11 . 1.535(3) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.521(3) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.524(3) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C14 . 1.543(3) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
N1 H1 . 0.8800 ?
C101 O101 . 1.236(3) ?
C101 N101 . 1.360(3) ?
C101 C102 . 1.508(3) ?
C102 C109 . 1.353(3) ?
C102 C103 . 1.486(3) ?
C103 C108 . 1.386(3) ?
C103 C104 . 1.407(3) ?
C104 C105 . 1.381(3) ?
C104 N101 . 1.396(3) ?
C105 C106 . 1.390(3) ?
C105 H105 . 0.9500 ?
C106 C107 . 1.389(3) ?
C106 H106 . 0.9500 ?
C107 C108 . 1.396(3) ?
C107 H107 . 0.9500 ?
C108 H108 . 0.9500 ?
C109 C114 . 1.501(3) ?
C109 C110 . 1.514(3) ?
C110 C111 . 1.529(3) ?
C110 H11C . 0.9900 ?
C110 H11D . 0.9900 ?
C111 C112 . 1.523(3) ?
C111 H11E . 0.9900 ?
C111 H11F . 0.9900 ?
C112 C113 . 1.527(3) ?
C112 H11G . 0.9900 ?
C112 H11H . 0.9900 ?
C113 C114 . 1.530(3) ?
C113 H11I . 0.9900 ?
C113 H11J . 0.9900 ?
C114 H11K . 0.9900 ?
C114 H11L . 0.9900 ?
N101 H101 . 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_865 0.88 1.97 2.846(2) 170.5 no
N101 H101 O101 2_756 0.88 1.98 2.850(2) 169.0 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 . . . . -4.4(4) ?
N1 C1 C2 C9 . . . . 173.8(2) ?
O1 C1 C2 C3 . . . . 179.2(2) ?
N1 C1 C2 C3 . . . . -2.6(2) ?
C9 C2 C3 C8 . . . . 8.3(4) ?
C1 C2 C3 C8 . . . . -175.7(2) ?
C9 C2 C3 C4 . . . . -174.0(2) ?
C1 C2 C3 C4 . . . . 2.0(2) ?
C8 C3 C4 C5 . . . . -2.7(3) ?
C2 C3 C4 C5 . . . . 179.1(2) ?
C8 C3 C4 N1 . . . . 177.43(19) ?
C2 C3 C4 N1 . . . . -0.7(2) ?
N1 C4 C5 C6 . . . . -179.1(2) ?
C3 C4 C5 C6 . . . . 1.1(3) ?
C4 C5 C6 C7 . . . . 0.6(3) ?
C5 C6 C7 C8 . . . . -0.6(4) ?
C4 C3 C8 C7 . . . . 2.7(3) ?
C2 C3 C8 C7 . . . . -179.8(2) ?
C6 C7 C8 C3 . . . . -1.1(4) ?
C3 C2 C9 C14 . . . . 179.5(2) ?
C1 C2 C9 C14 . . . . 4.1(3) ?
C3 C2 C9 C10 . . . . 3.6(4) ?
C1 C2 C9 C10 . . . . -171.7(2) ?
C2 C9 C10 C11 . . . . 118.1(2) ?
C14 C9 C10 C11 . . . . -58.3(3) ?
C9 C10 C11 C12 . . . . 57.3(3) ?
C10 C11 C12 C13 . . . . -55.9(2) ?
C11 C12 C13 C14 . . . . 54.8(2) ?
C2 C9 C14 C13 . . . . -119.5(2) ?
C10 C9 C14 C13 . . . . 56.8(2) ?
C12 C13 C14 C9 . . . . -54.9(2) ?
O1 C1 N1 C4 . . . . -179.4(2) ?
C2 C1 N1 C4 . . . . 2.2(2) ?
C5 C4 N1 C1 . . . . 179.2(2) ?
C3 C4 N1 C1 . . . . -1.0(2) ?
O101 C101 C102 C109 . . . . 5.8(4) ?
N101 C101 C102 C109 . . . . -171.8(2) ?
O101 C101 C102 C103 . . . . -178.0(2) ?
N101 C101 C102 C103 . . . . 4.5(2) ?
C109 C102 C103 C108 . . . . -12.0(4) ?
C101 C102 C103 C108 . . . . 172.1(2) ?
C109 C102 C103 C104 . . . . 172.8(2) ?
C101 C102 C103 C104 . . . . -3.1(2) ?
C108 C103 C104 C105 . . . . 3.2(3) ?
C102 C103 C104 C105 . . . . 179.4(2) ?
C108 C103 C104 N101 . . . . -175.44(19) ?
C102 C103 C104 N101 . . . . 0.8(2) ?
N101 C104 C105 C106 . . . . 177.0(2) ?
C103 C104 C105 C106 . . . . -1.4(3) ?
C104 C105 C106 C107 . . . . -0.9(3) ?
C105 C106 C107 C108 . . . . 1.4(4) ?
C104 C103 C108 C107 . . . . -2.7(3) ?
C102 C103 C108 C107 . . . . -177.6(2) ?
C106 C107 C108 C103 . . . . 0.5(3) ?
C103 C102 C109 C114 . . . . 174.2(2) ?
C101 C102 C109 C114 . . . . -10.6(3) ?
C103 C102 C109 C110 . . . . -6.2(4) ?
C101 C102 C109 C110 . . . . 169.0(2) ?
C102 C109 C110 C111 . . . . -128.4(2) ?
C114 C109 C110 C111 . . . . 51.2(3) ?
C109 C110 C111 C112 . . . . -53.8(3) ?
C110 C111 C112 C113 . . . . 57.1(3) ?
C111 C112 C113 C114 . . . . -56.8(2) ?
C102 C109 C114 C113 . . . . 127.6(2) ?
C110 C109 C114 C113 . . . . -52.0(2) ?
C112 C113 C114 C109 . . . . 54.5(2) ?
O101 C101 N101 C104 . . . . 178.0(2) ?
C102 C101 N101 C104 . . . . -4.3(2) ?
C105 C104 N101 C101 . . . . -176.3(2) ?
C103 C104 N101 C101 . . . . 2.3(2) ?
