#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/24/8102416.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8102416
loop_
_publ_author_name
'Bernard Tinant'
'Allan Urbach'
'Jacqueline Marchand-Brynaert'
_publ_section_title
;
 Crystal structure of
 (10R,11S,13R)-10-(methyl)-8,12-dioxo-13-(propyl)-9-oxa-1-aza-bicyclo[9.1.1]-tridecane,
 C15H25NO3
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              137
_journal_volume                  224
_journal_year                    2009
_chemical_formula_sum            'C15 H25 N O3'
_chemical_formula_weight         267.36
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.62(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.859(3)
_cell_length_b                   14.070(5)
_cell_length_c                   12.344(4)
_cell_measurement_reflns_used    all
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      24.4
_cell_measurement_theta_min      3.
_cell_volume                     1495.4(9)
_computing_cell_refinement       MAR
_computing_data_collection       MAR
_computing_data_reduction        MARHKL
_computing_molecular_graphics    'PLUTON [8]'
_computing_structure_refinement  'SHELXL-97 [7]'
_computing_structure_solution    'SHELXS-97 [7]'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 6.66
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '165 images, ΔΦ 3°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'RU200 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.053
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24648
_diffrn_reflns_theta_full        24.40
_diffrn_reflns_theta_max         24.40
_diffrn_reflns_theta_min         2.77
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelipiped
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(8)
_refine_ls_extinction_coef       0.057(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4918
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0339
_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)+(0.0327P)²+0.4442P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0873
_reflns_number_gt                4751
_reflns_number_total             4918
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2525.cff
_cod_data_source_block           au084
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 
;
_cod_original_sg_symbol_H-M      ' P 21 '
_cod_database_code               8102416
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.64149(19) 0.73371(11) 0.04399(12) 0.0324(4) Uani 1 1 d . . .
C2 C 0.5355(2) 0.66165(16) -0.01295(17) 0.0430(5) Uani 1 1 d . . .
H2A H 0.5128 0.6744 -0.0941 0.0456(9) Uiso 1 1 calc R . .
H2B H 0.4367 0.6672 0.0108 0.0456(9) Uiso 1 1 calc R . .
C3 C 0.5949(2) 0.55977(15) 0.00770(19) 0.0450(5) Uani 1 1 d . . .
H3A H 0.5042 0.5166 -0.0054 0.0456(9) Uiso 1 1 calc R . .
H3B H 0.6497 0.5538 0.0871 0.0456(9) Uiso 1 1 calc R . .
C4 C 0.7041(3) 0.52600(16) -0.06365(19) 0.0468(5) Uani 1 1 d . . .
H4A H 0.7216 0.4570 -0.0510 0.0456(9) Uiso 1 1 calc R . .
H4B H 0.6505 0.5346 -0.1430 0.0456(9) Uiso 1 1 calc R . .
C5 C 0.8619(2) 0.57451(14) -0.04405(15) 0.0372(4) Uani 1 1 d . . .
H5A H 0.9144 0.5533 -0.1024 0.0456(9) Uiso 1 1 calc R . .
H5B H 0.8456 0.6440 -0.0525 0.0456(9) Uiso 1 1 calc R . .
C6 C 0.9684(2) 0.55494(13) 0.06943(16) 0.0352(4) Uani 1 1 d . . .
H6A H 0.9930 0.4862 0.0757 0.0456(9) Uiso 1 1 calc R . .
H6B H 0.9134 0.5712 0.1280 0.0456(9) Uiso 1 1 calc R . .
C7 C 1.1200(2) 0.61138(16) 0.08948(19) 0.0424(5) Uani 1 1 d . . .
H7A H 1.1885 0.5907 0.1610 0.0456(9) Uiso 1 1 calc R . .
H7B H 1.1733 0.5962 0.0295 0.0456(9) Uiso 1 1 calc R . .
C8 C 1.0980(2) 0.71738(14) 0.09290(16) 0.0339(4) Uani 1 1 d . . .
O9 O 1.00419(16) 0.73988(9) 0.16082(12) 0.0392(3) Uani 1 1 d . . .
C10 C 0.9587(2) 0.83888(13) 0.16919(18) 0.0372(5) Uani 1 1 d . . .
H10 H 1.0102 0.8795 0.1220 0.0456(9) Uiso 1 1 calc R . .
C11 C 0.7838(2) 0.84311(13) 0.12430(15) 0.0309(4) Uani 1 1 d . . .
H11 H 0.7420 0.9081 0.1323 0.0456(9) Uiso 1 1 calc R . .
C12 C 0.7214(2) 0.80315(13) 0.00726(16) 0.0363(5) Uani 1 1 d . . .
C13 C 0.6834(2) 0.76443(12) 0.16164(13) 0.0260(4) Uani 1 1 d . . .
H13 H 0.7486 0.7161 0.2109 0.0456(9) Uiso 1 1 calc R . .
O14 O 1.15785(17) 0.77481(12) 0.04484(12) 0.0469(4) Uani 1 1 d . . .
C15 C 0.5482(2) 0.79717(14) 0.20765(16) 0.0333(4) Uani 1 1 d . . .
H15A H 0.4807 0.7420 0.2124 0.0456(9) Uiso 1 1 calc R . .
H15B H 0.4860 0.8438 0.1556 0.0456(9) Uiso 1 1 calc R . .
C16 C 0.5999(2) 0.84252(15) 0.32254(16) 0.0375(5) Uani 1 1 d . . .
H16A H 0.6567 0.7947 0.3756 0.0456(9) Uiso 1 1 calc R . .
H16B H 0.6726 0.8952 0.3187 0.0456(9) Uiso 1 1 calc R . .
C17 C 0.4659(3) 0.88064(16) 0.36604(19) 0.0449(5) Uani 1 1 d . . .
H17A H 0.5056 0.9089 0.4398 0.0456(9) Uiso 1 1 calc R . .
H17B H 0.3946 0.8286 0.3717 0.0456(9) Uiso 1 1 calc R . .
H17C H 0.4105 0.9292 0.3148 0.0456(9) Uiso 1 1 calc R . .
O18 O 0.7363(2) 0.82291(12) -0.08589(13) 0.0547(4) Uani 1 1 d . . .
C19 C 1.0111(2) 0.86941(16) 0.2887(2) 0.0487(6) Uani 1 1 d . . .
H19A H 1.1244 0.8646 0.3125 0.0456(9) Uiso 1 1 calc R . .
H19B H 0.9637 0.8282 0.3355 0.0456(9) Uiso 1 1 calc R . .
H19C H 0.9793 0.9353 0.2961 0.0456(9) Uiso 1 1 calc R . .
N101 N 1.29863(16) 0.69348(10) 0.70819(11) 0.0244(3) Uani 1 1 d . . .
C102 C 1.4191(2) 0.65053(13) 0.66272(15) 0.0299(4) Uani 1 1 d . . .
H10A H 1.4263 0.5822 0.6825 0.0456(9) Uiso 1 1 calc R . .
H10B H 1.5198 0.6803 0.6984 0.0456(9) Uiso 1 1 calc R . .
C103 C 1.3935(2) 0.65982(15) 0.53618(16) 0.0367(4) Uani 1 1 d . . .
H10C H 1.4226 0.7251 0.5189 0.0456(9) Uiso 1 1 calc R . .
H10D H 1.4648 0.6154 0.5109 0.0456(9) Uiso 1 1 calc R . .
C104 C 1.2292(2) 0.64031(14) 0.46916(16) 0.0382(5) Uani 1 1 d . . .
H10E H 1.2289 0.6410 0.3889 0.0456(9) Uiso 1 1 calc R . .
H10F H 1.1609 0.6925 0.4826 0.0456(9) Uiso 1 1 calc R . .
C105 C 1.1612(2) 0.54611(14) 0.49623(16) 0.0381(5) Uani 1 1 d . . .
H10G H 1.1571 0.5464 0.5757 0.0456(9) Uiso 1 1 calc R . .
H10H H 1.2315 0.4940 0.4858 0.0456(9) Uiso 1 1 calc R . .
C106 C 0.9984(3) 0.52568(16) 0.42476(19) 0.0489(6) Uani 1 1 d . . .
H10I H 1.0059 0.5169 0.3466 0.0456(9) Uiso 1 1 calc R . .
H10J H 0.9618 0.4649 0.4499 0.0456(9) Uiso 1 1 calc R . .
C107 C 0.8759(3) 0.60191(16) 0.42685(19) 0.0522(6) Uani 1 1 d . . .
H10K H 0.9067 0.6618 0.3958 0.0456(9) Uiso 1 1 calc R . .
H10L H 0.7753 0.5815 0.3788 0.0456(9) Uiso 1 1 calc R . .
C108 C 0.8561(2) 0.62009(15) 0.5422(2) 0.0438(5) Uani 1 1 d . . .
O109 O 0.94313(16) 0.69419(10) 0.58868(11) 0.0394(3) Uani 1 1 d . . .
C110 C 0.9385(2) 0.72673(15) 0.69994(16) 0.0357(4) Uani 1 1 d . . .
H110 H 0.8886 0.6772 0.7380 0.0456(9) Uiso 1 1 calc R . .
C111 C 1.1057(2) 0.74086(12) 0.76295(14) 0.0278(4) Uani 1 1 d . . .
H111 H 1.1149 0.7697 0.8383 0.0456(9) Uiso 1 1 calc R . .
C112 C 1.2050(2) 0.65198(12) 0.76639(14) 0.0268(4) Uani 1 1 d . . .
C113 C 1.21851(19) 0.78715(12) 0.69796(14) 0.0242(4) Uani 1 1 d . . .
H113 H 1.1644 0.8010 0.6189 0.0456(9) Uiso 1 1 calc R . .
O114 O 0.7741(2) 0.57542(13) 0.58898(18) 0.0684(5) Uani 1 1 d . . .
C115 C 1.3172(2) 0.87020(12) 0.75057(15) 0.0275(4) Uani 1 1 d . . .
H11A H 1.3789 0.8512 0.8251 0.0456(9) Uiso 1 1 calc R . .
H11B H 1.2485 0.9232 0.7609 0.0456(9) Uiso 1 1 calc R . .
C116 C 1.4271(2) 0.90468(13) 0.68030(17) 0.0323(4) Uani 1 1 d . . .
H11C H 1.4933 0.8508 0.6685 0.0456(9) Uiso 1 1 calc R . .
H11D H 1.3645 0.9245 0.6063 0.0456(9) Uiso 1 1 calc R . .
C117 C 1.5311(2) 0.98658(14) 0.73064(18) 0.0383(5) Uani 1 1 d . . .
H11E H 1.5978 1.0042 0.6808 0.0456(9) Uiso 1 1 calc R . .
H11F H 1.5958 0.9674 0.8031 0.0456(9) Uiso 1 1 calc R . .
H11G H 1.4670 1.0412 0.7406 0.0456(9) Uiso 1 1 calc R . .
O118 O 1.20274(16) 0.57134(9) 0.80275(11) 0.0354(3) Uani 1 1 d . . .
C119 C 0.8419(3) 0.81626(19) 0.6853(2) 0.0544(6) Uani 1 1 d . . .
H11H H 0.7356 0.8015 0.6444 0.0456(9) Uiso 1 1 calc R . .
H11I H 0.8871 0.8631 0.6433 0.0456(9) Uiso 1 1 calc R . .
H11J H 0.8402 0.8424 0.7586 0.0456(9) Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 C2 132.65(17) . . ?
C12 N1 C13 95.07(15) . . ?
C2 N1 C13 131.86(16) . . ?
N1 C2 C3 114.71(16) . . ?
N1 C2 H2A 108.6 . . ?
C3 C2 H2A 108.6 . . ?
N1 C2 H2B 108.6 . . ?
C3 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
C2 C3 C4 115.79(19) . . ?
C2 C3 H3A 108.3 . . ?
C4 C3 H3A 108.3 . . ?
C2 C3 H3B 108.3 . . ?
C4 C3 H3B 108.3 . . ?
H3A C3 H3B 107.4 . . ?
C5 C4 C3 116.80(17) . . ?
C5 C4 H4A 108.1 . . ?
C3 C4 H4A 108.1 . . ?
C5 C4 H4B 108.1 . . ?
C3 C4 H4B 108.1 . . ?
H4A C4 H4B 107.3 . . ?
C6 C5 C4 114.39(17) . . ?
C6 C5 H5A 108.7 . . ?
C4 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C5 C6 C7 112.73(17) . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C6 113.82(16) . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
O14 C8 O9 123.96(19) . . ?
O14 C8 C7 125.37(18) . . ?
O9 C8 C7 110.65(17) . . ?
C8 O9 C10 119.23(15) . . ?
O9 C10 C19 108.40(17) . . ?
O9 C10 C11 106.65(15) . . ?
C19 C10 C11 113.59(17) . . ?
O9 C10 H10 109.4 . . ?
C19 C10 H10 109.4 . . ?
C11 C10 H10 109.4 . . ?
C10 C11 C12 116.22(16) . . ?
C10 C11 C13 117.99(15) . . ?
C12 C11 C13 85.03(14) . . ?
C10 C11 H11 111.7 . . ?
C12 C11 H11 111.7 . . ?
C13 C11 H11 111.7 . . ?
O18 C12 N1 131.7(2) . . ?
O18 C12 C11 135.4(2) . . ?
N1 C12 C11 92.90(14) . . ?
N1 C13 C15 114.87(15) . . ?
N1 C13 C11 86.90(13) . . ?
C15 C13 C11 116.93(15) . . ?
N1 C13 H13 112.0 . . ?
C15 C13 H13 112.0 . . ?
C11 C13 H13 112.0 . . ?
C13 C15 C16 112.69(15) . . ?
C13 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
C13 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C15 112.94(17) . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C112 N101 C102 128.75(15) . . ?
C112 N101 C113 95.03(13) . . ?
C102 N101 C113 135.74(14) . . ?
N101 C102 C103 114.45(15) . . ?
N101 C102 H10A 108.6 . . ?
C103 C102 H10A 108.6 . . ?
N101 C102 H10B 108.6 . . ?
C103 C102 H10B 108.6 . . ?
H10A C102 H10B 107.6 . . ?
C104 C103 C102 115.65(16) . . ?
C104 C103 H10C 108.4 . . ?
C102 C103 H10C 108.4 . . ?
C104 C103 H10D 108.4 . . ?
C102 C103 H10D 108.4 . . ?
H10C C103 H10D 107.4 . . ?
C103 C104 C105 114.50(16) . . ?
C103 C104 H10E 108.6 . . ?
C105 C104 H10E 108.6 . . ?
C103 C104 H10F 108.6 . . ?
C105 C104 H10F 108.6 . . ?
H10E C104 H10F 107.6 . . ?
C104 C105 C106 113.84(17) . . ?
C104 C105 H10G 108.8 . . ?
C106 C105 H10G 108.8 . . ?
C104 C105 H10H 108.8 . . ?
C106 C105 H10H 108.8 . . ?
H10G C105 H10H 107.7 . . ?
C107 C106 C105 115.74(17) . . ?
C107 C106 H10I 108.3 . . ?
C105 C106 H10I 108.3 . . ?
C107 C106 H10J 108.3 . . ?
C105 C106 H10J 108.3 . . ?
H10I C106 H10J 107.4 . . ?
C108 C107 C106 112.22(18) . . ?
C108 C107 H10K 109.2 . . ?
C106 C107 H10K 109.2 . . ?
C108 C107 H10L 109.2 . . ?
C106 C107 H10L 109.2 . . ?
H10K C107 H10L 107.9 . . ?
O114 C108 O109 123.4(2) . . ?
O114 C108 C107 125.8(2) . . ?
O109 C108 C107 110.76(18) . . ?
C108 O109 C110 120.36(16) . . ?
O109 C110 C119 106.87(17) . . ?
O109 C110 C111 106.48(14) . . ?
C119 C110 C111 114.20(18) . . ?
O109 C110 H110 109.7 . . ?
C119 C110 H110 109.7 . . ?
C111 C110 H110 109.7 . . ?
C110 C111 C112 113.25(15) . . ?
C110 C111 C113 117.20(14) . . ?
C112 C111 C113 85.50(13) . . ?
C110 C111 H111 112.7 . . ?
C112 C111 H111 112.7 . . ?
C113 C111 H111 112.7 . . ?
O118 C112 N101 131.43(17) . . ?
O118 C112 C111 135.47(16) . . ?
N101 C112 C111 93.05(13) . . ?
N101 C113 C115 115.61(14) . . ?
N101 C113 C111 86.40(12) . . ?
C115 C113 C111 118.46(14) . . ?
N101 C113 H113 111.4 . . ?
C115 C113 H113 111.4 . . ?
C111 C113 H113 111.4 . . ?
C113 C115 C116 112.53(15) . . ?
C113 C115 H11A 109.1 . . ?
C116 C115 H11A 109.1 . . ?
C113 C115 H11B 109.1 . . ?
C116 C115 H11B 109.1 . . ?
H11A C115 H11B 107.8 . . ?
C117 C116 C115 114.60(17) . . ?
C117 C116 H11C 108.6 . . ?
C115 C116 H11C 108.6 . . ?
C117 C116 H11D 108.6 . . ?
C115 C116 H11D 108.6 . . ?
H11C C116 H11D 107.6 . . ?
C116 C117 H11E 109.5 . . ?
C116 C117 H11F 109.5 . . ?
H11E C117 H11F 109.5 . . ?
C116 C117 H11G 109.5 . . ?
H11E C117 H11G 109.5 . . ?
H11F C117 H11G 109.5 . . ?
C110 C119 H11H 109.5 . . ?
C110 C119 H11I 109.5 . . ?
H11H C119 H11I 109.5 . . ?
C110 C119 H11J 109.5 . . ?
H11H C119 H11J 109.5 . . ?
H11I C119 H11J 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C12 1.346(3) . ?
N1 C2 1.446(3) . ?
N1 C13 1.476(2) . ?
C2 C3 1.528(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.529(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.523(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.518(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.529(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.506(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O14 1.198(2) . ?
C8 O9 1.350(2) . ?
O9 C10 1.460(2) . ?
C10 C19 1.501(3) . ?
C10 C11 1.518(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.527(3) . ?
C11 C13 1.557(3) . ?
C11 H11 1.0000 . ?
C12 O18 1.220(2) . ?
C13 C15 1.513(2) . ?
C13 H13 1.0000 . ?
C15 C16 1.524(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.512(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
N101 C112 1.351(2) . ?
N101 C102 1.450(2) . ?
N101 C113 1.488(2) . ?
C102 C103 1.530(3) . ?
C102 H10A 0.9900 . ?
C102 H10B 0.9900 . ?
C103 C104 1.520(3) . ?
C103 H10C 0.9900 . ?
C103 H10D 0.9900 . ?
C104 C105 1.525(3) . ?
C104 H10E 0.9900 . ?
C104 H10F 0.9900 . ?
C105 C106 1.531(3) . ?
C105 H10G 0.9900 . ?
C105 H10H 0.9900 . ?
C106 C107 1.530(3) . ?
C106 H10I 0.9900 . ?
C106 H10J 0.9900 . ?
C107 C108 1.498(4) . ?
C107 H10K 0.9900 . ?
C107 H10L 0.9900 . ?
C108 O114 1.205(3) . ?
C108 O109 1.342(3) . ?
O109 C110 1.457(3) . ?
C110 C119 1.510(3) . ?
C110 C111 1.516(3) . ?
C110 H110 1.0000 . ?
C111 C112 1.524(3) . ?
C111 C113 1.563(2) . ?
C111 H111 1.0000 . ?
C112 O118 1.222(2) . ?
C113 C115 1.511(2) . ?
C113 H113 1.0000 . ?
C115 C116 1.528(3) . ?
C115 H11A 0.9900 . ?
C115 H11B 0.9900 . ?
C116 C117 1.514(3) . ?
C116 H11C 0.9900 . ?
C116 H11D 0.9900 . ?
C117 H11E 0.9800 . ?
C117 H11F 0.9800 . ?
C117 H11G 0.9800 . ?
C119 H11H 0.9800 . ?
C119 H11I 0.9800 . ?
C119 H11J 0.9800 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 C2 C3 113.5(2) . . . . ?
C13 N1 C2 C3 -75.9(3) . . . . ?
N1 C2 C3 C4 -82.2(2) . . . . ?
C2 C3 C4 C5 66.3(2) . . . . ?
C3 C4 C5 C6 66.7(2) . . . . ?
C4 C5 C6 C7 -175.21(16) . . . . ?
C5 C6 C7 C8 64.3(2) . . . . ?
C6 C7 C8 O14 -133.2(2) . . . . ?
C6 C7 C8 O9 48.6(2) . . . . ?
O14 C8 O9 C10 6.4(3) . . . . ?
C7 C8 O9 C10 -175.45(17) . . . . ?
C8 O9 C10 C19 -121.30(19) . . . . ?
C8 O9 C10 C11 116.03(18) . . . . ?
O9 C10 C11 C12 -54.4(2) . . . . ?
C19 C10 C11 C12 -173.78(16) . . . . ?
O9 C10 C11 C13 44.3(2) . . . . ?
C19 C10 C11 C13 -75.0(2) . . . . ?
C2 N1 C12 O18 -5.3(4) . . . . ?
C13 N1 C12 O18 -178.3(2) . . . . ?
C2 N1 C12 C11 175.6(2) . . . . ?
C13 N1 C12 C11 2.57(14) . . . . ?
C10 C11 C12 O18 -62.6(3) . . . . ?
C13 C11 C12 O18 178.5(2) . . . . ?
C10 C11 C12 N1 116.40(17) . . . . ?
C13 C11 C12 N1 -2.43(14) . . . . ?
C12 N1 C13 C15 115.83(16) . . . . ?
C2 N1 C13 C15 -57.3(3) . . . . ?
C12 N1 C13 C11 -2.52(14) . . . . ?
C2 N1 C13 C11 -175.62(19) . . . . ?
C10 C11 C13 N1 -114.91(17) . . . . ?
C12 C11 C13 N1 2.22(12) . . . . ?
C10 C11 C13 C15 128.67(18) . . . . ?
C12 C11 C13 C15 -114.20(16) . . . . ?
N1 C13 C15 C16 -170.94(16) . . . . ?
C11 C13 C15 C16 -71.2(2) . . . . ?
C13 C15 C16 C17 176.59(17) . . . . ?
C112 N101 C102 C103 120.34(19) . . . . ?
C113 N101 C102 C103 -49.6(3) . . . . ?
N101 C102 C103 C104 -43.9(2) . . . . ?
C102 C103 C104 C105 -51.9(2) . . . . ?
C103 C104 C105 C106 -177.65(17) . . . . ?
C104 C105 C106 C107 -55.8(3) . . . . ?
C105 C106 C107 C108 -58.3(3) . . . . ?
C106 C107 C108 O114 -84.7(3) . . . . ?
C106 C107 C108 O109 95.2(2) . . . . ?
O114 C108 O109 C110 -2.0(3) . . . . ?
C107 C108 O109 C110 178.07(16) . . . . ?
C108 O109 C110 C119 -103.9(2) . . . . ?
C108 O109 C110 C111 133.70(16) . . . . ?
O109 C110 C111 C112 -56.39(18) . . . . ?
C119 C110 C111 C112 -174.08(16) . . . . ?
O109 C110 C111 C113 40.8(2) . . . . ?
C119 C110 C111 C113 -76.9(2) . . . . ?
C102 N101 C112 O118 5.9(3) . . . . ?
C113 N101 C112 O118 178.83(19) . . . . ?
C102 N101 C112 C111 -171.79(16) . . . . ?
C113 N101 C112 C111 1.16(14) . . . . ?
C110 C111 C112 O118 -60.9(3) . . . . ?
C113 C111 C112 O118 -178.6(2) . . . . ?
C110 C111 C112 N101 116.62(15) . . . . ?
C113 C111 C112 N101 -1.11(13) . . . . ?
C112 N101 C113 C115 118.83(15) . . . . ?
C102 N101 C113 C115 -69.1(2) . . . . ?
C112 N101 C113 C111 -1.13(13) . . . . ?
C102 N101 C113 C111 170.99(18) . . . . ?
C110 C111 C113 N101 -112.88(16) . . . . ?
C112 C111 C113 N101 1.00(12) . . . . ?
C110 C111 C113 C115 129.83(17) . . . . ?
C112 C111 C113 C115 -116.29(16) . . . . ?
N101 C113 C115 C116 76.73(19) . . . . ?
C111 C113 C115 C116 177.14(15) . . . . ?
C113 C115 C116 C117 -178.76(16) . . . . ?
