#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:11:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178424 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/45/4024552.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_4024552
loop_
_publ_author_name
'Nicoleta Toşa'
'Attila Bende'
'Richard Attila Varga'
'Anamaria Terec'
'Ioan Bratu'
'Ion Grosu'
_publ_section_title
;
H-Bond-Driven Supramolecular Architectures of the Syn and Anti Isomers of the
Dioxime of Bicyclo[3.3.1]nonane-3,7-dione
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3944
_journal_page_last               3947
_journal_paper_doi               10.1021/jo900484v
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C9 H14 N2 O2'
_chemical_formula_weight         182.22
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 107.626(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   12.7815(15)
_cell_length_b                   11.2772(13)
_cell_length_c                   20.068(2)
_cell_measurement_reflns_used    3133
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      22.99
_cell_measurement_theta_min      2.46
_cell_volume                     2756.8(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0453
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25920
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9814
_exptl_absorpt_correction_T_min  0.9759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker, 2001.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         2.127
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.206
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.735
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4859
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.735
_refine_ls_R_factor_all          0.1869
_refine_ls_R_factor_gt           0.1720
_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/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4249
_refine_ls_wR_factor_ref         0.4340
_reflns_number_gt                4031
_reflns_number_total             4859
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900484v_si_004.cif
_cod_data_source_block           369rich
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               4024552
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
N3 N 0.8958(4) 0.8461(4) 0.0111(2) 0.0310(11) Uani 1 1 d . . .
N6 N 0.8402(4) 0.5964(4) 0.9026(2) 0.0331(12) Uani 1 1 d . . .
C1 C 0.9312(4) 0.5146(5) 0.1473(3) 0.0272(12) Uani 1 1 d . . .
C2 C 0.9446(5) 0.5928(5) 0.2093(3) 0.0389(15) Uani 1 1 d . . .
H2C H 0.9350 0.6749 0.1942 0.047 Uiso 1 1 calc R . .
H2D H 1.0183 0.5840 0.2411 0.047 Uiso 1 1 calc R . .
C3 C 0.8604(5) 0.5619(5) 0.2481(3) 0.0320(14) Uani 1 1 d . . .
H3A H 0.8795 0.6059 0.2922 0.038 Uiso 1 1 calc R . .
C4 C 0.7436(5) 0.5938(5) 0.2058(3) 0.0404(15) Uani 1 1 d . . .
H4A H 0.6959 0.5855 0.2350 0.048 Uiso 1 1 calc R . .
H4B H 0.7412 0.6760 0.1912 0.048 Uiso 1 1 calc R . .
C5 C 0.7016(4) 0.5154(4) 0.1416(3) 0.0253(12) Uani 1 1 d . . .
C6 C 0.7214(4) 0.3851(4) 0.1526(3) 0.0249(12) Uani 1 1 d . . .
H6A H 0.7080 0.3464 0.1076 0.030 Uiso 1 1 calc R . .
H6B H 0.6702 0.3527 0.1750 0.030 Uiso 1 1 calc R . .
C7 C 0.8402(4) 0.3590(4) 0.1984(2) 0.0175(11) Uani 1 1 d . . .
H7 H 0.8453 0.2746 0.2106 0.021 Uiso 1 1 calc R . .
C8 C 0.9213(4) 0.3847(4) 0.1584(3) 0.0264(12) Uani 1 1 d . . .
H8A H 0.9927 0.3532 0.1842 0.032 Uiso 1 1 calc R . .
H8B H 0.8974 0.3451 0.1134 0.032 Uiso 1 1 calc R . .
C9 C 0.8665(5) 0.4296(5) 0.2645(3) 0.0326(14) Uani 1 1 d . . .
H9A H 0.9397 0.4097 0.2941 0.039 Uiso 1 1 calc R . .
H9B H 0.8149 0.4102 0.2897 0.039 Uiso 1 1 calc R . .
C10 C 0.8703(4) 0.9549(5) 0.0082(3) 0.0271(12) Uani 1 1 d . . .
C11 C 0.8810(4) 1.0334(5) 0.0703(3) 0.0321(13) Uani 1 1 d . . .
H11A H 0.9426 1.0867 0.0759 0.038 Uiso 1 1 calc R . .
H11B H 0.8962 0.9848 0.1121 0.038 Uiso 1 1 calc R . .
C12 C 0.7789(4) 1.1052(4) 0.0630(3) 0.0275(13) Uani 1 1 d . . .
H12 H 0.7957 1.1627 0.1015 0.033 Uiso 1 1 calc R . .
C13 C 0.6824(5) 1.0302(5) 0.0682(3) 0.0319(13) Uani 1 1 d . . .
H13A H 0.7062 0.9795 0.1091 0.038 Uiso 1 1 calc R . .
H13B H 0.6250 1.0818 0.0740 0.038 Uiso 1 1 calc R . .
C14 C 0.6370(4) 0.9547(5) 0.0041(3) 0.0247(12) Uani 1 1 d . . .
C15 C 0.6224(5) 1.0112(5) -0.0658(3) 0.0345(14) Uani 1 1 d . . .
H15A H 0.5572 1.0606 -0.0778 0.041 Uiso 1 1 calc R . .
H15B H 0.6117 0.9498 -0.1011 0.041 Uiso 1 1 calc R . .
C16 C 0.7222(4) 1.0870(5) -0.0658(3) 0.0284(13) Uani 1 1 d . . .
H16 H 0.7034 1.1322 -0.1096 0.034 Uiso 1 1 calc R . .
C17 C 0.8229(5) 1.0117(5) -0.0618(3) 0.0330(13) Uani 1 1 d . . .
H17A H 0.8028 0.9504 -0.0974 0.040 Uiso 1 1 calc R . .
H17B H 0.8784 1.0612 -0.0718 0.040 Uiso 1 1 calc R . .
C18 C 0.7481(5) 1.1749(5) -0.0054(3) 0.0386(16) Uani 1 1 d . . .
H18A H 0.6846 1.2243 -0.0088 0.046 Uiso 1 1 calc R . .
H18B H 0.8085 1.2258 -0.0069 0.046 Uiso 1 1 calc R . .
C19 C 0.5631(4) 0.5364(5) 0.8416(3) 0.0275(13) Uani 1 1 d . . .
C20 C 0.5465(5) 0.5886(5) 0.7716(3) 0.0374(15) Uani 1 1 d . . .
H20A H 0.5496 0.6743 0.7757 0.045 Uiso 1 1 calc R . .
H20B H 0.4740 0.5673 0.7417 0.045 Uiso 1 1 calc R . .
C21 C 0.6320(5) 0.5472(4) 0.7377(3) 0.0302(13) Uani 1 1 d . . .
H21 H 0.6107 0.5756 0.6893 0.036 Uiso 1 1 calc R . .
C22 C 0.7450(5) 0.5948(5) 0.7759(3) 0.0369(14) Uani 1 1 d . . .
H22A H 0.7936 0.5797 0.7479 0.044 Uiso 1 1 calc R . .
H22B H 0.7404 0.6800 0.7810 0.044 Uiso 1 1 calc R . .
C23 C 0.7935(4) 0.5402(5) 0.8470(3) 0.0296(13) Uani 1 1 d . . .
C24 C 0.7806(4) 0.4061(5) 0.8518(3) 0.0303(13) Uani 1 1 d . . .
H24A H 0.8334 0.3666 0.8335 0.036 Uiso 1 1 calc R . .
H24B H 0.7962 0.3836 0.9005 0.036 Uiso 1 1 calc R . .
C25 C 0.6652(4) 0.3654(4) 0.8112(3) 0.0250(12) Uani 1 1 d . . .
H25 H 0.6650 0.2785 0.8092 0.030 Uiso 1 1 calc R . .
C26 C 0.5813(4) 0.4043(5) 0.8469(3) 0.0324(14) Uani 1 1 d . . .
H26A H 0.5123 0.3640 0.8254 0.039 Uiso 1 1 calc R . .
H26B H 0.6069 0.3816 0.8958 0.039 Uiso 1 1 calc R . .
C27 C 0.6333(5) 0.4122(4) 0.7373(3) 0.0301(13) Uani 1 1 d . . .
H27A H 0.5611 0.3827 0.7114 0.036 Uiso 1 1 calc R . .
H27B H 0.6853 0.3844 0.7142 0.036 Uiso 1 1 calc R . .
N1 N 0.9232(3) 0.5642(4) 0.0879(2) 0.0301(11) Uani 1 1 d . . .
N2 N 0.6564(3) 0.5621(4) 0.0830(2) 0.0282(11) Uani 1 1 d . . .
N4 N 0.6118(4) 0.8447(4) 0.0055(2) 0.0328(11) Uani 1 1 d . . .
N5 N 0.5677(4) 0.5939(4) 0.8980(2) 0.0316(11) Uani 1 1 d . . .
O1 O 0.9061(3) 0.4818(4) 0.0315(2) 0.0440(12) Uani 1 1 d . . .
O2 O 0.6218(3) 0.4780(3) 0.0262(2) 0.0414(11) Uani 1 1 d . . .
O3 O 0.9424(4) 0.8048(4) 0.0816(2) 0.0531(13) Uani 1 1 d . . .
O4 O 0.6255(4) 0.8025(3) 0.0755(2) 0.0480(12) Uani 1 1 d . . .
O5 O 0.5473(3) 0.7181(4) 0.8848(2) 0.0465(12) Uani 1 1 d . . .
O6 O 0.8493(4) 0.7200(4) 0.8890(2) 0.0475(12) Uani 1 1 d . . .
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
C10 N3 O3 112.6(4) . . ?
C23 N6 O6 111.3(5) . . ?
N1 C1 C2 118.1(5) . . ?
N1 C1 C8 125.1(5) . . ?
C2 C1 C8 116.7(5) . . ?
C1 C2 C3 111.4(4) . . ?
C1 C2 H2C 109.4 . . ?
C3 C2 H2C 109.4 . . ?
C1 C2 H2D 109.4 . . ?
C3 C2 H2D 109.4 . . ?
H2C C2 H2D 108.0 . . ?
C4 C3 C9 109.3(4) . . ?
C4 C3 C2 112.4(5) . . ?
C9 C3 C2 109.3(5) . . ?
C4 C3 H3A 108.6 . . ?
C9 C3 H3A 108.6 . . ?
C2 C3 H3A 108.6 . . ?
C5 C4 C3 111.7(4) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
N2 C5 C6 123.9(5) . . ?
N2 C5 C4 119.5(5) . . ?
C6 C5 C4 116.5(4) . . ?
C5 C6 C7 111.5(4) . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C9 C7 C8 111.1(4) . . ?
C9 C7 C6 110.0(4) . . ?
C8 C7 C6 110.8(4) . . ?
C9 C7 H7 108.3 . . ?
C8 C7 H7 108.3 . . ?
C6 C7 H7 108.3 . . ?
C1 C8 C7 111.6(4) . . ?
C1 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C1 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C7 C9 C3 110.3(4) . . ?
C7 C9 H9A 109.6 . . ?
C3 C9 H9A 109.6 . . ?
C7 C9 H9B 109.6 . . ?
C3 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
N3 C10 C17 118.9(5) . . ?
N3 C10 C11 125.2(5) . . ?
C17 C10 C11 115.9(5) . . ?
C10 C11 C12 112.2(4) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13 113.0(5) . . ?
C11 C12 C18 110.1(5) . . ?
C13 C12 C18 110.7(4) . . ?
C11 C12 H12 107.6 . . ?
C13 C12 H12 107.6 . . ?
C18 C12 H12 107.6 . . ?
C14 C13 C12 111.4(4) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
N4 C14 C15 118.0(5) . . ?
N4 C14 C13 124.2(5) . . ?
C15 C14 C13 117.8(5) . . ?
C14 C15 C16 111.6(4) . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C17 C16 C18 110.2(4) . . ?
C17 C16 C15 112.2(5) . . ?
C18 C16 C15 110.0(4) . . ?
C17 C16 H16 108.1 . . ?
C18 C16 H16 108.1 . . ?
C15 C16 H16 108.1 . . ?
C10 C17 C16 112.5(4) . . ?
C10 C17 H17A 109.1 . . ?
C16 C17 H17A 109.1 . . ?
C10 C17 H17B 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C16 C18 C12 108.4(4) . . ?
C16 C18 H18A 110.0 . . ?
C12 C18 H18A 110.0 . . ?
C16 C18 H18B 110.0 . . ?
C12 C18 H18B 110.0 . . ?
H18A C18 H18B 108.4 . . ?
N5 C19 C20 126.1(5) . . ?
N5 C19 C26 118.0(5) . . ?
C20 C19 C26 115.8(5) . . ?
C19 C20 C21 112.7(4) . . ?
C19 C20 H20A 109.0 . . ?
C21 C20 H20A 109.0 . . ?
C19 C20 H20B 109.0 . . ?
C21 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C22 C21 C27 110.3(4) . . ?
C22 C21 C20 111.6(5) . . ?
C27 C21 C20 108.6(5) . . ?
C22 C21 H21 108.8 . . ?
C27 C21 H21 108.8 . . ?
C20 C21 H21 108.8 . . ?
C23 C22 C21 113.0(4) . . ?
C23 C22 H22A 109.0 . . ?
C21 C22 H22A 109.0 . . ?
C23 C22 H22B 109.0 . . ?
C21 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
N6 C23 C22 125.5(5) . . ?
N6 C23 C24 118.1(5) . . ?
C22 C23 C24 116.4(4) . . ?
C25 C24 C23 111.7(4) . . ?
C25 C24 H24A 109.3 . . ?
C23 C24 H24A 109.3 . . ?
C25 C24 H24B 109.3 . . ?
C23 C24 H24B 109.3 . . ?
H24A C24 H24B 107.9 . . ?
C27 C25 C26 110.0(4) . . ?
C27 C25 C24 110.4(4) . . ?
C26 C25 C24 111.5(4) . . ?
C27 C25 H25 108.3 . . ?
C26 C25 H25 108.3 . . ?
C24 C25 H25 108.3 . . ?
C19 C26 C25 111.6(4) . . ?
C19 C26 H26A 109.3 . . ?
C25 C26 H26A 109.3 . . ?
C19 C26 H26B 109.3 . . ?
C25 C26 H26B 109.3 . . ?
H26A C26 H26B 108.0 . . ?
C25 C27 C21 110.2(4) . . ?
C25 C27 H27A 109.6 . . ?
C21 C27 H27A 109.6 . . ?
C25 C27 H27B 109.6 . . ?
C21 C27 H27B 109.6 . . ?
H27A C27 H27B 108.1 . . ?
C1 N1 O1 113.6(4) . . ?
C5 N2 O2 114.0(4) . . ?
C14 N4 O4 112.5(4) . . ?
C19 N5 O5 111.8(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
N3 C10 1.266(7) . ?
N3 O3 1.435(6) . ?
N6 C23 1.266(7) . ?
N6 O6 1.432(6) . ?
C1 N1 1.293(7) . ?
C1 C2 1.492(7) . ?
C1 C8 1.493(7) . ?
C2 C3 1.546(8) . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C3 C4 1.521(8) . ?
C3 C9 1.524(7) . ?
C3 H3A 0.9800 . ?
C4 C5 1.520(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N2 1.259(6) . ?
C5 C6 1.495(7) . ?
C6 C7 1.547(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C9 1.497(6) . ?
C7 C8 1.519(6) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C17 1.497(7) . ?
C10 C11 1.500(7) . ?
C11 C12 1.505(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.524(8) . ?
C12 C18 1.527(7) . ?
C12 H12 0.9800 . ?
C13 C14 1.506(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N4 1.284(7) . ?
C14 C15 1.499(7) . ?
C15 C16 1.537(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.523(8) . ?
C16 C18 1.523(7) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 N5 1.290(7) . ?
C19 C20 1.477(7) . ?
C19 C26 1.507(8) . ?
C20 C21 1.525(8) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.514(8) . ?
C21 C27 1.522(7) . ?
C21 H21 0.9800 . ?
C22 C23 1.504(7) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.526(7) . ?
C24 C25 1.525(7) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C27 1.510(7) . ?
C25 C26 1.523(7) . ?
C25 H25 0.9800 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
N1 O1 1.430(6) . ?
N2 O2 1.445(6) . ?
N4 O4 1.443(6) . ?
N5 O5 1.434(6) . ?
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
N1 C1 C2 C3 129.0(5) . . . . ?
C8 C1 C2 C3 -47.4(7) . . . . ?
C1 C2 C3 C4 -68.9(6) . . . . ?
C1 C2 C3 C9 52.6(6) . . . . ?
C9 C3 C4 C5 -53.1(6) . . . . ?
C2 C3 C4 C5 68.5(6) . . . . ?
C3 C4 C5 N2 -131.3(5) . . . . ?
C3 C4 C5 C6 46.3(7) . . . . ?
N2 C5 C6 C7 132.3(5) . . . . ?
C4 C5 C6 C7 -45.2(6) . . . . ?
C5 C6 C7 C9 52.3(5) . . . . ?
C5 C6 C7 C8 -71.0(5) . . . . ?
N1 C1 C8 C7 -129.4(5) . . . . ?
C2 C1 C8 C7 46.8(6) . . . . ?
C9 C7 C8 C1 -52.3(6) . . . . ?
C6 C7 C8 C1 70.3(5) . . . . ?
C8 C7 C9 C3 60.8(6) . . . . ?
C6 C7 C9 C3 -62.3(6) . . . . ?
C4 C3 C9 C7 63.0(6) . . . . ?
C2 C3 C9 C7 -60.5(6) . . . . ?
O3 N3 C10 C17 178.7(4) . . . . ?
O3 N3 C10 C11 -2.9(7) . . . . ?
N3 C10 C11 C12 -132.5(6) . . . . ?
C17 C10 C11 C12 45.9(6) . . . . ?
C10 C11 C12 C13 70.1(6) . . . . ?
C10 C11 C12 C18 -54.3(6) . . . . ?
C11 C12 C13 C14 -72.0(6) . . . . ?
C18 C12 C13 C14 52.1(6) . . . . ?
C12 C13 C14 N4 135.1(5) . . . . ?
C12 C13 C14 C15 -43.6(6) . . . . ?
N4 C14 C15 C16 -134.8(5) . . . . ?
C13 C14 C15 C16 44.0(7) . . . . ?
C14 C15 C16 C17 70.4(6) . . . . ?
C14 C15 C16 C18 -52.6(6) . . . . ?
N3 C10 C17 C16 133.7(5) . . . . ?
C11 C10 C17 C16 -44.8(6) . . . . ?
C18 C16 C17 C10 52.3(6) . . . . ?
C15 C16 C17 C10 -70.6(6) . . . . ?
C17 C16 C18 C12 -61.4(5) . . . . ?
C15 C16 C18 C12 62.8(5) . . . . ?
C11 C12 C18 C16 62.7(5) . . . . ?
C13 C12 C18 C16 -63.0(5) . . . . ?
N5 C19 C20 C21 129.0(6) . . . . ?
C26 C19 C20 C21 -47.9(7) . . . . ?
C19 C20 C21 C22 -67.9(6) . . . . ?
C19 C20 C21 C27 53.9(6) . . . . ?
C27 C21 C22 C23 -51.1(6) . . . . ?
C20 C21 C22 C23 69.7(6) . . . . ?
O6 N6 C23 C22 -4.6(7) . . . . ?
O6 N6 C23 C24 178.0(4) . . . . ?
C21 C22 C23 N6 -133.9(6) . . . . ?
C21 C22 C23 C24 43.6(7) . . . . ?
N6 C23 C24 C25 134.0(5) . . . . ?
C22 C23 C24 C25 -43.7(7) . . . . ?
C23 C24 C25 C27 52.0(6) . . . . ?
C23 C24 C25 C26 -70.7(6) . . . . ?
N5 C19 C26 C25 -130.4(5) . . . . ?
C20 C19 C26 C25 46.7(6) . . . . ?
C27 C25 C26 C19 -52.5(6) . . . . ?
C24 C25 C26 C19 70.4(5) . . . . ?
C26 C25 C27 C21 61.6(6) . . . . ?
C24 C25 C27 C21 -61.9(6) . . . . ?
C22 C21 C27 C25 61.1(6) . . . . ?
C20 C21 C27 C25 -61.5(6) . . . . ?
C2 C1 N1 O1 -177.6(4) . . . . ?
C8 C1 N1 O1 -1.5(7) . . . . ?
C6 C5 N2 O2 1.6(7) . . . . ?
C4 C5 N2 O2 179.0(4) . . . . ?
C15 C14 N4 O4 -177.7(4) . . . . ?
C13 C14 N4 O4 3.6(7) . . . . ?
C20 C19 N5 O5 3.9(7) . . . . ?
C26 C19 N5 O5 -179.2(4) . . . . ?
