#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:09:59 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178423 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/44/4024458.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_4024458
loop_
_publ_author_name
'Syed Masood Husain'
'Roland Fröhlich'
'Dirk Schepmann'
'Bernhard Wünsch'
_publ_section_title
;
Asymmetric Synthesis of Enantiomerically Pure 2-Substituted
Tetrahydro-3-benzazepines and Their Affinity to σ1 Receptors
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2788
_journal_page_last               2793
_journal_paper_doi               10.1021/jo900087e
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H21 N O2'
_chemical_formula_weight         355.42
_chemical_name_systematic
; 
 ? 
;
_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   'at N17 from difmap, other geom'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.127(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            6
_cell_length_a                   10.7594(3)
_cell_length_b                   24.0248(7)
_cell_length_c                   11.8032(4)
_cell_measurement_reflns_used    6795
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      0.88
_cell_volume                     2864.72(15)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect /Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25641
_diffrn_reflns_theta_full        68.10
_diffrn_reflns_theta_max         68.10
_diffrn_reflns_theta_min         4.80
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  0.8863
_exptl_absorpt_correction_T_min  0.7900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.023
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.15(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     745
_refine_ls_number_reflns         8522
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0344
_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)+(0.0211P)²+0.4809P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0792
_reflns_number_gt                8087
_reflns_number_total             8522
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900087e_si_002.cif
_cod_data_source_block           fro4147
_cod_original_sg_symbol_H-M      P21
_cod_database_code               4024458
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
C1A C 0.10720(17) 0.73259(9) 0.97357(16) 0.0462(4) Uani 1 1 d . . .
C2A C 0.0720(2) 0.67477(9) 0.95282(17) 0.0516(5) Uani 1 1 d . . .
O2A O -0.03197(15) 0.65554(6) 0.87998(13) 0.0623(4) Uani 1 1 d . . .
C3A C 0.1821(2) 0.63933(10) 1.0365(2) 0.0614(5) Uani 1 1 d . . .
H3AA H 0.1487 0.6149 1.0860 0.074 Uiso 1 1 calc R . .
H3AB H 0.2242 0.6166 0.9909 0.074 Uiso 1 1 calc R . .
C4A C 0.27671(19) 0.68168(10) 1.11287(18) 0.0553(5) Uani 1 1 d . . .
C5A C 0.3882(2) 0.67213(13) 1.2128(2) 0.0687(7) Uani 1 1 d . . .
H5A H 0.4162 0.6356 1.2367 0.082 Uiso 1 1 calc R . .
C6A C 0.4576(2) 0.71659(14) 1.2767(2) 0.0762(8) Uani 1 1 d . . .
H6A H 0.5324 0.7105 1.3460 0.091 Uiso 1 1 calc R . .
C7A C 0.4184(2) 0.76989(13) 1.2399(2) 0.0723(7) Uani 1 1 d . . .
H7A H 0.4678 0.7999 1.2839 0.087 Uiso 1 1 calc R . .
C8A C 0.30710(19) 0.78049(11) 1.13914(19) 0.0596(5) Uani 1 1 d . . .
H8A H 0.2817 0.8172 1.1146 0.072 Uiso 1 1 calc R . .
C9A C 0.23409(17) 0.73569(10) 1.07526(17) 0.0502(5) Uani 1 1 d . . .
C10A C 0.02445(17) 0.77474(8) 0.90946(16) 0.0448(4) Uani 1 1 d . . .
C11A C 0.05814(17) 0.83501(8) 0.93676(15) 0.0448(4) Uani 1 1 d . . .
C12A C 0.00845(19) 0.86421(9) 1.01267(17) 0.0503(4) Uani 1 1 d . . .
H12A H -0.0484 0.8463 1.0463 0.060 Uiso 1 1 calc R . .
C13A C 0.0415(2) 0.91932(9) 1.03952(19) 0.0579(5) Uani 1 1 d . . .
H13A H 0.0074 0.9385 1.0917 0.069 Uiso 1 1 calc R . .
C14A C 0.1235(2) 0.94644(10) 0.9912(2) 0.0632(6) Uani 1 1 d . . .
H14A H 0.1441 0.9842 1.0082 0.076 Uiso 1 1 calc R . .
C15A C 0.1753(3) 0.91736(12) 0.9171(2) 0.0771(7) Uani 1 1 d . . .
H15A H 0.2325 0.9354 0.8840 0.093 Uiso 1 1 calc R . .
C16A C 0.1441(2) 0.86190(11) 0.8908(2) 0.0673(6) Uani 1 1 d . . .
H16A H 0.1815 0.8424 0.8414 0.081 Uiso 1 1 calc R . .
N17A N -0.08916(15) 0.76242(8) 0.82286(15) 0.0524(4) Uani 1 1 d . . .
H17A H -0.108(2) 0.7253(12) 0.815(2) 0.063(7) Uiso 1 1 d . . .
C18A C -0.18604(18) 0.80099(9) 0.74467(17) 0.0506(5) Uani 1 1 d . . .
H18A H -0.1373 0.8341 0.7326 0.061 Uiso 1 1 calc R . .
C19A C -0.28417(18) 0.82046(8) 0.80235(16) 0.0475(4) Uani 1 1 d . . .
C20A C -0.36121(19) 0.78347(9) 0.83995(18) 0.0534(5) Uani 1 1 d . . .
H20A H -0.3560 0.7451 0.8265 0.064 Uiso 1 1 calc R . .
C21A C -0.4456(2) 0.80273(12) 0.8971(2) 0.0650(6) Uani 1 1 d . . .
H21A H -0.4966 0.7771 0.9225 0.078 Uiso 1 1 calc R . .
C22A C -0.4562(2) 0.85812(13) 0.9173(2) 0.0755(7) Uani 1 1 d . . .
H22A H -0.5138 0.8705 0.9565 0.091 Uiso 1 1 calc R . .
C23A C -0.3816(3) 0.89586(12) 0.8796(3) 0.0787(8) Uani 1 1 d . . .
H23A H -0.3880 0.9342 0.8929 0.094 Uiso 1 1 calc R . .
C24A C -0.2970(2) 0.87663(9) 0.8218(2) 0.0630(6) Uani 1 1 d . . .
H24A H -0.2472 0.9024 0.7954 0.076 Uiso 1 1 calc R . .
C25A C -0.2479(2) 0.77224(11) 0.6215(2) 0.0648(6) Uani 1 1 d . . .
H25A H -0.3285 0.7922 0.5744 0.078 Uiso 1 1 calc R . .
H25B H -0.1857 0.7743 0.5774 0.078 Uiso 1 1 calc R . .
O26A O -0.27935(14) 0.71614(7) 0.63241(16) 0.0742(5) Uani 1 1 d . . .
H26A H -0.3610 0.7125 0.6098 0.111 Uiso 1 1 calc R . .
C1B C 0.23770(17) 0.66734(8) 0.44072(16) 0.0422(4) Uani 1 1 d . . .
C2B C 0.37503(18) 0.66068(9) 0.50707(16) 0.0458(4) Uani 1 1 d . . .
O2B O 0.45134(12) 0.69654(6) 0.57176(12) 0.0546(3) Uani 1 1 d . . .
C3B C 0.4170(2) 0.60242(9) 0.4873(2) 0.0568(5) Uani 1 1 d . . .
H3BA H 0.4872 0.6034 0.4520 0.068 Uiso 1 1 calc R . .
H3BB H 0.4487 0.5816 0.5633 0.068 Uiso 1 1 calc R . .
C4B C 0.2935(2) 0.57694(9) 0.40165(19) 0.0538(5) Uani 1 1 d . . .
C5B C 0.2730(3) 0.52508(10) 0.3466(2) 0.0721(7) Uani 1 1 d . . .
H5B H 0.3441 0.5002 0.3603 0.087 Uiso 1 1 calc R . .
C6B C 0.1478(3) 0.51006(11) 0.2715(3) 0.0796(7) Uani 1 1 d . . .
H6B H 0.1342 0.4751 0.2334 0.096 Uiso 1 1 calc R . .
C7B C 0.0434(3) 0.54579(10) 0.2524(2) 0.0713(6) Uani 1 1 d . . .
H7B H -0.0418 0.5346 0.2032 0.086 Uiso 1 1 calc R . .
C8B C 0.0617(2) 0.59842(8) 0.30491(19) 0.0541(5) Uani 1 1 d . . .
H8B H -0.0104 0.6228 0.2910 0.065 Uiso 1 1 calc R . .
C9B C 0.18750(19) 0.61451(8) 0.37785(17) 0.0458(4) Uani 1 1 d . . .
C10B C 0.17269(16) 0.71792(7) 0.43233(15) 0.0384(4) Uani 1 1 d . . .
C11B C 0.03321(16) 0.72650(7) 0.35046(15) 0.0372(3) Uani 1 1 d . . .
C12B C -0.07027(17) 0.72651(8) 0.39537(16) 0.0435(4) Uani 1 1 d . . .
H12B H -0.0534 0.7211 0.4782 0.052 Uiso 1 1 calc R . .
C13B C -0.19793(18) 0.73453(9) 0.31769(19) 0.0522(5) Uani 1 1 d . . .
H13B H -0.2677 0.7353 0.3485 0.063 Uiso 1 1 calc R . .
C14B C -0.22484(19) 0.74142(9) 0.19687(19) 0.0559(5) Uani 1 1 d . . .
H14B H -0.3125 0.7463 0.1446 0.067 Uiso 1 1 calc R . .
C15B C -0.1222(2) 0.74115(11) 0.15218(19) 0.0617(6) Uani 1 1 d . . .
H15B H -0.1400 0.7460 0.0690 0.074 Uiso 1 1 calc R . .
C16B C 0.00626(19) 0.73389(10) 0.22849(17) 0.0541(5) Uani 1 1 d . . .
H16B H 0.0758 0.7340 0.1974 0.065 Uiso 1 1 calc R . .
N17B N 0.23668(15) 0.76116(6) 0.49747(14) 0.0431(3) Uani 1 1 d . . .
H17B H 0.322(2) 0.7535(9) 0.5406(18) 0.049(5) Uiso 1 1 d . . .
C18B C 0.19113(17) 0.81859(7) 0.49124(16) 0.0424(4) Uani 1 1 d . . .
H18B H 0.1030 0.8211 0.4273 0.051 Uiso 1 1 calc R . .
C19B C 0.28511(18) 0.85660(7) 0.45729(15) 0.0429(4) Uani 1 1 d . . .
C20B C 0.2408(2) 0.88667(9) 0.35066(18) 0.0559(5) Uani 1 1 d . . .
H20B H 0.1521 0.8835 0.2997 0.067 Uiso 1 1 calc R . .
C21B C 0.3254(3) 0.92127(11) 0.3184(2) 0.0699(7) Uani 1 1 d . . .
H21B H 0.2938 0.9418 0.2463 0.084 Uiso 1 1 calc R . .
C22B C 0.4559(2) 0.92588(10) 0.3912(2) 0.0677(6) Uani 1 1 d . . .
H22B H 0.5139 0.9489 0.3685 0.081 Uiso 1 1 calc R . .
C23B C 0.5008(2) 0.89643(9) 0.4977(2) 0.0581(5) Uani 1 1 d . . .
H23B H 0.5896 0.8998 0.5482 0.070 Uiso 1 1 calc R . .
C24B C 0.41676(19) 0.86200(8) 0.53069(17) 0.0484(4) Uani 1 1 d . . .
H24B H 0.4487 0.8420 0.6035 0.058 Uiso 1 1 calc R . .
C25B C 0.1763(2) 0.83459(9) 0.61044(18) 0.0513(4) Uani 1 1 d . . .
H25C H 0.2605 0.8281 0.6759 0.062 Uiso 1 1 calc R . .
H25D H 0.1563 0.8744 0.6092 0.062 Uiso 1 1 calc R . .
O26B O 0.07560(14) 0.80429(6) 0.63413(13) 0.0559(3) Uani 1 1 d . . .
H26B H 0.1010 0.7719 0.6530 0.084 Uiso 1 1 calc R . .
C1C C 0.21586(17) 0.59998(8) 0.72517(16) 0.0422(4) Uani 1 1 d . . .
C2C C 0.19865(17) 0.65917(8) 0.72898(15) 0.0417(4) Uani 1 1 d . . .
O2C O 0.09564(12) 0.68647(5) 0.68009(12) 0.0481(3) Uani 1 1 d . . .
C3C C 0.32889(18) 0.68519(8) 0.80400(18) 0.0481(4) Uani 1 1 d . . .
H3CA H 0.3575 0.7129 0.7571 0.058 Uiso 1 1 calc R . .
H3CB H 0.3219 0.7031 0.8762 0.058 Uiso 1 1 calc R . .
C4C C 0.42302(18) 0.63703(9) 0.83735(16) 0.0466(4) Uani 1 1 d . . .
C5C C 0.5567(2) 0.63697(10) 0.90387(19) 0.0593(5) Uani 1 1 d . . .
H5C H 0.5993 0.6701 0.9389 0.071 Uiso 1 1 calc R . .
C6C C 0.6277(2) 0.58777(12) 0.9186(2) 0.0665(6) Uani 1 1 d . . .
H6C H 0.7188 0.5874 0.9634 0.080 Uiso 1 1 calc R . .
C7C C 0.5645(2) 0.53938(11) 0.8673(2) 0.0643(6) Uani 1 1 d . . .
H7C H 0.6135 0.5062 0.8770 0.077 Uiso 1 1 calc R . .
C8C C 0.4304(2) 0.53861(10) 0.80176(19) 0.0549(5) Uani 1 1 d . . .
H8C H 0.3889 0.5052 0.7672 0.066 Uiso 1 1 calc R . .
C9C C 0.35728(17) 0.58756(8) 0.78719(15) 0.0434(4) Uani 1 1 d . . .
C10C C 0.11023(17) 0.56348(8) 0.67569(16) 0.0425(4) Uani 1 1 d . . .
C11C C 0.13063(17) 0.50224(8) 0.67158(18) 0.0480(4) Uani 1 1 d . . .
C12C C 0.1179(2) 0.47758(10) 0.5624(2) 0.0629(5) Uani 1 1 d . . .
H12C H 0.0965 0.4993 0.4920 0.075 Uiso 1 1 calc R . .
C13C C 0.1368(3) 0.42087(12) 0.5568(3) 0.0863(8) Uani 1 1 d . . .
H13C H 0.1276 0.4041 0.4824 0.104 Uiso 1 1 calc R . .
C14C C 0.1688(3) 0.38908(12) 0.6587(4) 0.0962(10) Uani 1 1 d . . .
H14C H 0.1821 0.3506 0.6543 0.115 Uiso 1 1 calc R . .
C15C C 0.1813(3) 0.41297(12) 0.7665(3) 0.0852(8) Uani 1 1 d . . .
H15C H 0.2032 0.3908 0.8363 0.102 Uiso 1 1 calc R . .
C16C C 0.1620(2) 0.46989(10) 0.7746(2) 0.0641(6) Uani 1 1 d . . .
H16C H 0.1701 0.4862 0.8492 0.077 Uiso 1 1 calc R . .
N17C N -0.01377(15) 0.58200(7) 0.62687(15) 0.0489(4) Uani 1 1 d . . .
H17C H -0.020(2) 0.6173(12) 0.631(2) 0.071(8) Uiso 1 1 d . . .
C18C C -0.13257(17) 0.54765(8) 0.60023(17) 0.0463(4) Uani 1 1 d . . .
H18C H -0.1026 0.5088 0.6215 0.056 Uiso 1 1 calc R . .
C19C C -0.21724(17) 0.54785(8) 0.46815(17) 0.0467(4) Uani 1 1 d . . .
C20C C -0.2347(2) 0.59389(10) 0.3954(2) 0.0671(6) Uani 1 1 d . . .
H20C H -0.1924 0.6274 0.4279 0.081 Uiso 1 1 calc R . .
C21C C -0.3129(2) 0.59163(11) 0.2757(2) 0.0729(7) Uani 1 1 d . . .
H21C H -0.3231 0.6236 0.2276 0.087 Uiso 1 1 calc R . .
C22C C -0.3759(2) 0.54387(12) 0.2259(2) 0.0712(6) Uani 1 1 d . . .
H22C H -0.4293 0.5426 0.1440 0.085 Uiso 1 1 calc R . .
C23C C -0.3600(3) 0.49805(12) 0.2970(2) 0.0891(9) Uani 1 1 d . . .
H23C H -0.4026 0.4647 0.2638 0.107 Uiso 1 1 calc R . .
C24C C -0.2820(3) 0.49999(10) 0.4172(2) 0.0759(7) Uani 1 1 d . . .
H24C H -0.2730 0.4680 0.4651 0.091 Uiso 1 1 calc R . .
C25C C -0.2078(2) 0.56490(9) 0.68286(19) 0.0534(5) Uani 1 1 d . . .
H25E H -0.2255 0.6050 0.6748 0.064 Uiso 1 1 calc R . .
H25F H -0.2929 0.5454 0.6588 0.064 Uiso 1 1 calc R . .
O26C O -0.13371(15) 0.55216(6) 0.80441(13) 0.0627(4) Uani 1 1 d . . .
H26C H -0.0891 0.5797 0.8371 0.094 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C10A C1A C2A 121.97(17) . . ?
C10A C1A C9A 130.26(18) . . ?
C2A C1A C9A 107.62(17) . . ?
O2A C2A C1A 126.81(19) . . ?
O2A C2A C3A 123.9(2) . . ?
C1A C2A C3A 109.28(17) . . ?
C4A C3A C2A 103.13(19) . . ?
C5A C4A C9A 121.3(2) . . ?
C5A C4A C3A 127.6(2) . . ?
C9A C4A C3A 110.98(17) . . ?
C6A C5A C4A 119.3(3) . . ?
C7A C6A C5A 120.2(2) . . ?
C6A C7A C8A 121.5(2) . . ?
C7A C8A C9A 118.8(2) . . ?
C8A C9A C4A 118.94(18) . . ?
C8A C9A C1A 132.1(2) . . ?
C4A C9A C1A 108.79(18) . . ?
N17A C10A C1A 120.28(19) . . ?
N17A C10A C11A 118.06(17) . . ?
C1A C10A C11A 121.64(15) . . ?
C16A C11A C12A 118.50(19) . . ?
C16A C11A C10A 120.76(18) . . ?
C12A C11A C10A 120.68(17) . . ?
C13A C12A C11A 120.6(2) . . ?
C14A C13A C12A 120.9(2) . . ?
C13A C14A C15A 118.9(2) . . ?
C14A C15A C16A 120.7(2) . . ?
C11A C16A C15A 120.4(2) . . ?
C10A N17A C18A 127.72(19) . . ?
N17A C18A C19A 111.61(16) . . ?
N17A C18A C25A 107.12(18) . . ?
C19A C18A C25A 114.95(16) . . ?
C24A C19A C20A 117.8(2) . . ?
C24A C19A C18A 120.05(19) . . ?
C20A C19A C18A 122.12(18) . . ?
C21A C20A C19A 120.4(2) . . ?
C22A C21A C20A 121.3(2) . . ?
C21A C22A C23A 119.4(2) . . ?
C22A C23A C24A 119.4(2) . . ?
C19A C24A C23A 121.6(2) . . ?
O26A C25A C18A 112.56(19) . . ?
C10B C1B C2B 122.66(17) . . ?
C10B C1B C9B 128.95(15) . . ?
C2B C1B C9B 108.12(16) . . ?
O2B C2B C1B 126.64(18) . . ?
O2B C2B C3B 124.23(17) . . ?
C1B C2B C3B 109.13(17) . . ?
C4B C3B C2B 103.86(16) . . ?
C5B C4B C9B 119.7(2) . . ?
C5B C4B C3B 130.18(19) . . ?
C9B C4B C3B 110.10(18) . . ?
C6B C5B C4B 119.9(2) . . ?
C7B C6B C5B 120.4(2) . . ?
C6B C7B C8B 120.9(2) . . ?
C9B C8B C7B 119.21(19) . . ?
C8B C9B C4B 119.82(18) . . ?
C8B C9B C1B 131.49(17) . . ?
C4B C9B C1B 108.69(16) . . ?
N17B C10B C1B 119.54(15) . . ?
N17B C10B C11B 118.02(15) . . ?
C1B C10B C11B 122.43(15) . . ?
C16B C11B C12B 119.38(16) . . ?
C16B C11B C10B 119.79(15) . . ?
C12B C11B C10B 120.82(15) . . ?
C13B C12B C11B 119.53(17) . . ?
C14B C13B C12B 121.15(18) . . ?
C13B C14B C15B 119.33(17) . . ?
C16B C15B C14B 120.44(19) . . ?
C15B C16B C11B 120.17(18) . . ?
C10B N17B C18B 127.59(15) . . ?
N17B C18B C19B 109.90(15) . . ?
N17B C18B C25B 109.48(15) . . ?
C19B C18B C25B 112.63(14) . . ?
C20B C19B C24B 118.43(18) . . ?
C20B C19B C18B 120.14(16) . . ?
C24B C19B C18B 121.43(16) . . ?
C21B C20B C19B 120.74(19) . . ?
C22B C21B C20B 120.3(2) . . ?
C21B C22B C23B 119.4(2) . . ?
C22B C23B C24B 120.6(2) . . ?
C23B C24B C19B 120.50(18) . . ?
O26B C25B C18B 112.68(15) . . ?
C10C C1C C2C 122.70(16) . . ?
C10C C1C C9C 129.33(17) . . ?
C2C C1C C9C 107.87(15) . . ?
O2C C2C C1C 127.61(17) . . ?
O2C C2C C3C 123.47(17) . . ?
C1C C2C C3C 108.92(15) . . ?
C4C C3C C2C 103.95(16) . . ?
C5C C4C C9C 120.88(19) . . ?
C5C C4C C3C 128.88(19) . . ?
C9C C4C C3C 110.22(15) . . ?
C4C C5C C6C 119.6(2) . . ?
C7C C6C C5C 119.83(19) . . ?
C6C C7C C8C 121.3(2) . . ?
C7C C8C C9C 119.6(2) . . ?
C8C C9C C4C 118.75(17) . . ?
C8C C9C C1C 132.47(18) . . ?
C4C C9C C1C 108.78(17) . . ?
N17C C10C C1C 121.38(17) . . ?
N17C C10C C11C 116.84(16) . . ?
C1C C10C C11C 121.75(16) . . ?
C12C C11C C16C 119.7(2) . . ?
C12C C11C C10C 119.01(18) . . ?
C16C C11C C10C 121.33(19) . . ?
C11C C12C C13C 119.8(2) . . ?
C14C C13C C12C 120.4(3) . . ?
C15C C14C C13C 120.2(3) . . ?
C14C C15C C16C 120.6(3) . . ?
C11C C16C C15C 119.3(3) . . ?
C10C N17C C18C 125.08(17) . . ?
N17C C18C C19C 113.09(16) . . ?
N17C C18C C25C 109.05(15) . . ?
C19C C18C C25C 113.28(15) . . ?
C24C C19C C20C 117.51(19) . . ?
C24C C19C C18C 118.97(18) . . ?
C20C C19C C18C 123.51(18) . . ?
C19C C20C C21C 121.0(2) . . ?
C22C C21C C20C 121.0(2) . . ?
C23C C22C C21C 118.6(2) . . ?
C22C C23C C24C 120.7(2) . . ?
C19C C24C C23C 121.1(2) . . ?
O26C C25C C18C 110.64(16) . . ?
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
C1A C10A 1.388(3) . ?
C1A C2A 1.439(3) . ?
C1A C9A 1.477(3) . ?
C2A O2A 1.242(2) . ?
C2A C3A 1.516(3) . ?
C3A C4A 1.501(3) . ?
C4A C5A 1.382(3) . ?
C4A C9A 1.397(3) . ?
C5A C6A 1.371(4) . ?
C6A C7A 1.371(4) . ?
C7A C8A 1.390(3) . ?
C8A C9A 1.392(3) . ?
C10A N17A 1.329(2) . ?
C10A C11A 1.500(3) . ?
C11A C16A 1.383(3) . ?
C11A C12A 1.382(3) . ?
C12A C13A 1.379(3) . ?
C13A C14A 1.369(3) . ?
C14A C15A 1.378(4) . ?
C15A C16A 1.383(4) . ?
N17A C18A 1.461(3) . ?
C18A C19A 1.514(3) . ?
C18A C25A 1.538(3) . ?
C19A C24A 1.384(3) . ?
C19A C20A 1.388(3) . ?
C20A C21A 1.384(3) . ?
C21A C22A 1.364(4) . ?
C22A C23A 1.382(4) . ?
C23A C24A 1.391(4) . ?
C25A O26A 1.406(3) . ?
C1B C10B 1.389(2) . ?
C1B C2B 1.423(3) . ?
C1B C9B 1.476(3) . ?
C2B O2B 1.252(2) . ?
C2B C3B 1.514(3) . ?
C3B C4B 1.496(3) . ?
C4B C5B 1.388(3) . ?
C4B C9B 1.405(3) . ?
C5B C6B 1.381(4) . ?
C6B C7B 1.369(4) . ?
C7B C8B 1.392(3) . ?
C8B C9B 1.386(3) . ?
C10B N17B 1.334(2) . ?
C10B C11B 1.493(2) . ?
C11B C16B 1.379(3) . ?
C11B C12B 1.388(2) . ?
C12B C13B 1.378(3) . ?
C13B C14B 1.364(3) . ?
C14B C15B 1.378(3) . ?
C15B C16B 1.377(3) . ?
N17B C18B 1.457(2) . ?
C18B C19B 1.515(3) . ?
C18B C25B 1.519(3) . ?
C19B C20B 1.386(3) . ?
C19B C24B 1.389(3) . ?
C20B C21B 1.380(3) . ?
C21B C22B 1.375(3) . ?
C22B C23B 1.376(3) . ?
C23B C24B 1.378(3) . ?
C25B O26B 1.411(2) . ?
C1C C10C 1.395(3) . ?
C1C C2C 1.437(3) . ?
C1C C9C 1.474(3) . ?
C2C O2C 1.246(2) . ?
C2C C3C 1.512(3) . ?
C3C C4C 1.498(3) . ?
C4C C5C 1.382(3) . ?
C4C C9C 1.405(3) . ?
C5C C6C 1.385(4) . ?
C6C C7C 1.378(4) . ?
C7C C8C 1.383(3) . ?
C8C C9C 1.392(3) . ?
C10C N17C 1.335(2) . ?
C10C C11C 1.491(3) . ?
C11C C12C 1.382(3) . ?
C11C C16C 1.383(3) . ?
C12C C13C 1.383(4) . ?
C13C C14C 1.365(5) . ?
C14C C15C 1.360(5) . ?
C15C C16C 1.392(4) . ?
N17C C18C 1.462(2) . ?
C18C C19C 1.511(3) . ?
C18C C25C 1.523(3) . ?
C19C C24C 1.371(3) . ?
C19C C20C 1.373(3) . ?
C20C C21C 1.374(3) . ?
C21C C22C 1.359(4) . ?
C22C C23C 1.358(4) . ?
C23C C24C 1.379(4) . ?
C25C O26C 1.414(2) . ?
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
C10A C1A C2A O2A -0.9(3) . . . . ?
C9A C1A C2A O2A 175.13(19) . . . . ?
C10A C1A C2A C3A -179.96(17) . . . . ?
C9A C1A C2A C3A -3.9(2) . . . . ?
O2A C2A C3A C4A -174.59(19) . . . . ?
C1A C2A C3A C4A 4.5(2) . . . . ?
C2A C3A C4A C5A 172.6(2) . . . . ?
C2A C3A C4A C9A -3.5(2) . . . . ?
C9A C4A C5A C6A 0.5(3) . . . . ?
C3A C4A C5A C6A -175.3(2) . . . . ?
C4A C5A C6A C7A -1.5(3) . . . . ?
C5A C6A C7A C8A 1.1(4) . . . . ?
C6A C7A C8A C9A 0.4(3) . . . . ?
C7A C8A C9A C4A -1.4(3) . . . . ?
C7A C8A C9A C1A 173.6(2) . . . . ?
C5A C4A C9A C8A 1.0(3) . . . . ?
C3A C4A C9A C8A 177.40(18) . . . . ?
C5A C4A C9A C1A -175.12(18) . . . . ?
C3A C4A C9A C1A 1.3(2) . . . . ?
C10A C1A C9A C8A 1.8(3) . . . . ?
C2A C1A C9A C8A -173.7(2) . . . . ?
C10A C1A C9A C4A 177.25(19) . . . . ?
C2A C1A C9A C4A 1.7(2) . . . . ?
C2A C1A C10A N17A -2.5(3) . . . . ?
C9A C1A C10A N17A -177.48(18) . . . . ?
C2A C1A C10A C11A 176.25(17) . . . . ?
C9A C1A C10A C11A 1.2(3) . . . . ?
N17A C10A C11A C16A -99.4(2) . . . . ?
C1A C10A C11A C16A 81.9(2) . . . . ?
N17A C10A C11A C12A 83.4(2) . . . . ?
C1A C10A C11A C12A -95.3(2) . . . . ?
C16A C11A C12A C13A 1.5(3) . . . . ?
C10A C11A C12A C13A 178.75(17) . . . . ?
C11A C12A C13A C14A 0.4(3) . . . . ?
C12A C13A C14A C15A -1.5(3) . . . . ?
C13A C14A C15A C16A 0.7(4) . . . . ?
C12A C11A C16A C15A -2.3(3) . . . . ?
C10A C11A C16A C15A -179.6(2) . . . . ?
C14A C15A C16A C11A 1.3(4) . . . . ?
C1A C10A N17A C18A -178.27(19) . . . . ?
C11A C10A N17A C18A 3.0(3) . . . . ?
C10A N17A C18A C19A -86.8(2) . . . . ?
C10A N17A C18A C25A 146.5(2) . . . . ?
N17A C18A C19A C24A 121.4(2) . . . . ?
C25A C18A C19A C24A -116.3(2) . . . . ?
N17A C18A C19A C20A -57.0(2) . . . . ?
C25A C18A C19A C20A 65.3(2) . . . . ?
C24A C19A C20A C21A -1.3(3) . . . . ?
C18A C19A C20A C21A 177.15(18) . . . . ?
C19A C20A C21A C22A 0.5(3) . . . . ?
C20A C21A C22A C23A 0.2(3) . . . . ?
C21A C22A C23A C24A -0.1(3) . . . . ?
C20A C19A C24A C23A 1.5(3) . . . . ?
C18A C19A C24A C23A -177.00(19) . . . . ?
C22A C23A C24A C19A -0.8(3) . . . . ?
N17A C18A C25A O26A 43.8(2) . . . . ?
C19A C18A C25A O26A -80.8(2) . . . . ?
C10B C1B C2B O2B 5.5(3) . . . . ?
C9B C1B C2B O2B -179.89(18) . . . . ?
C10B C1B C2B C3B -174.24(17) . . . . ?
C9B C1B C2B C3B 0.3(2) . . . . ?
O2B C2B C3B C4B -178.26(18) . . . . ?
C1B C2B C3B C4B 1.5(2) . . . . ?
C2B C3B C4B C5B 176.5(2) . . . . ?
C2B C3B C4B C9B -2.9(2) . . . . ?
C9B C4B C5B C6B -1.9(4) . . . . ?
C3B C4B C5B C6B 178.7(2) . . . . ?
C4B C5B C6B C7B -0.9(4) . . . . ?
C5B C6B C7B C8B 2.0(4) . . . . ?
C6B C7B C8B C9B -0.3(4) . . . . ?
C7B C8B C9B C4B -2.5(3) . . . . ?
C7B C8B C9B C1B 177.3(2) . . . . ?
C5B C4B C9B C8B 3.6(3) . . . . ?
C3B C4B C9B C8B -176.94(19) . . . . ?
C5B C4B C9B C1B -176.2(2) . . . . ?
C3B C4B C9B C1B 3.2(2) . . . . ?
C10B C1B C9B C8B -7.9(3) . . . . ?
C2B C1B C9B C8B 178.0(2) . . . . ?
C10B C1B C9B C4B 171.91(18) . . . . ?
C2B C1B C9B C4B -2.2(2) . . . . ?
C2B C1B C10B N17B -6.5(3) . . . . ?
C9B C1B C10B N17B -179.89(18) . . . . ?
C2B C1B C10B C11B 172.14(17) . . . . ?
C9B C1B C10B C11B -1.2(3) . . . . ?
N17B C10B C11B C16B 101.2(2) . . . . ?
C1B C10B C11B C16B -77.4(2) . . . . ?
N17B C10B C11B C12B -79.5(2) . . . . ?
C1B C10B C11B C12B 101.8(2) . . . . ?
C16B C11B C12B C13B -0.7(3) . . . . ?
C10B C11B C12B C13B 180.00(17) . . . . ?
C11B C12B C13B C14B 1.3(3) . . . . ?
C12B C13B C14B C15B -1.0(3) . . . . ?
C13B C14B C15B C16B 0.1(4) . . . . ?
C14B C15B C16B C11B 0.4(4) . . . . ?
C12B C11B C16B C15B -0.1(3) . . . . ?
C10B C11B C16B C15B 179.2(2) . . . . ?
C1B C10B N17B C18B 172.62(16) . . . . ?
C11B C10B N17B C18B -6.1(3) . . . . ?
C10B N17B C18B C19B -119.61(18) . . . . ?
C10B N17B C18B C25B 116.18(19) . . . . ?
N17B C18B C19B C20B 117.31(19) . . . . ?
C25B C18B C19B C20B -120.3(2) . . . . ?
N17B C18B C19B C24B -62.2(2) . . . . ?
C25B C18B C19B C24B 60.1(2) . . . . ?
C24B C19B C20B C21B -0.2(3) . . . . ?
C18B C19B C20B C21B -179.8(2) . . . . ?
C19B C20B C21B C22B 0.8(4) . . . . ?
C20B C21B C22B C23B -1.1(4) . . . . ?
C21B C22B C23B C24B 0.8(4) . . . . ?
C22B C23B C24B C19B -0.2(3) . . . . ?
C20B C19B C24B C23B -0.1(3) . . . . ?
C18B C19B C24B C23B 179.45(19) . . . . ?
N17B C18B C25B O26B -65.6(2) . . . . ?
C19B C18B C25B O26B 171.79(16) . . . . ?
C10C C1C C2C O2C -8.2(3) . . . . ?
C9C C1C C2C O2C 175.08(17) . . . . ?
C10C C1C C2C C3C 171.78(17) . . . . ?
C9C C1C C2C C3C -4.9(2) . . . . ?
O2C C2C C3C C4C -177.19(16) . . . . ?
C1C C2C C3C C4C 2.78(19) . . . . ?
C2C C3C C4C C5C 178.70(19) . . . . ?
C2C C3C C4C C9C 0.5(2) . . . . ?
C9C C4C C5C C6C 1.8(3) . . . . ?
C3C C4C C5C C6C -176.3(2) . . . . ?
C4C C5C C6C C7C -0.3(3) . . . . ?
C5C C6C C7C C8C -0.6(4) . . . . ?
C6C C7C C8C C9C -0.1(3) . . . . ?
C7C C8C C9C C4C 1.6(3) . . . . ?
C7C C8C C9C C1C -179.2(2) . . . . ?
C5C C4C C9C C8C -2.4(3) . . . . ?
C3C C4C C9C C8C 175.94(17) . . . . ?
C5C C4C C9C C1C 178.14(18) . . . . ?
C3C C4C C9C C1C -3.5(2) . . . . ?
C10C C1C C9C C8C 9.5(3) . . . . ?
C2C C1C C9C C8C -174.1(2) . . . . ?
C10C C1C C9C C4C -171.16(18) . . . . ?
C2C C1C C9C C4C 5.2(2) . . . . ?
C2C C1C C10C N17C 1.1(3) . . . . ?
C9C C1C C10C N17C 177.05(18) . . . . ?
C2C C1C C10C C11C 179.36(17) . . . . ?
C9C C1C C10C C11C -4.7(3) . . . . ?
N17C C10C C11C C12C 71.9(2) . . . . ?
C1C C10C C11C C12C -106.4(2) . . . . ?
N17C C10C C11C C16C -108.1(2) . . . . ?
C1C C10C C11C C16C 73.6(3) . . . . ?
C16C C11C C12C C13C -0.1(3) . . . . ?
C10C C11C C12C C13C 179.8(2) . . . . ?
C11C C12C C13C C14C -0.4(4) . . . . ?
C12C C13C C14C C15C 0.5(5) . . . . ?
C13C C14C C15C C16C -0.1(4) . . . . ?
C12C C11C C16C C15C 0.5(3) . . . . ?
C10C C11C C16C C15C -179.4(2) . . . . ?
C14C C15C C16C C11C -0.4(4) . . . . ?
C1C C10C N17C C18C -164.13(18) . . . . ?
C11C C10C N17C C18C 17.6(3) . . . . ?
C10C N17C C18C C19C -120.3(2) . . . . ?
C10C N17C C18C C25C 112.7(2) . . . . ?
N17C C18C C19C C24C 144.2(2) . . . . ?
C25C C18C C19C C24C -91.1(2) . . . . ?
N17C C18C C19C C20C -36.6(3) . . . . ?
C25C C18C C19C C20C 88.1(2) . . . . ?
C24C C19C C20C C21C -0.7(4) . . . . ?
C18C C19C C20C C21C -180.0(2) . . . . ?
C19C C20C C21C C22C 0.3(4) . . . . ?
C20C C21C C22C C23C 0.0(4) . . . . ?
C21C C22C C23C C24C 0.2(5) . . . . ?
C20C C19C C24C C23C 1.0(4) . . . . ?
C18C C19C C24C C23C -179.7(3) . . . . ?
C22C C23C C24C C19C -0.7(5) . . . . ?
N17C C18C C25C O26C -66.2(2) . . . . ?
C19C C18C C25C O26C 166.90(16) . . . . ?
