#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:03:07 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180370 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/39/7203902.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_7203902
loop_
_publ_author_name
'von Hirschheydt, Thomas'
'Wolfart, Volker'
'Gleiter, Rolf'
'Irngartinger, Hermann'
'Oeser, Thomas'
'Rominger, Frank'
'Eisenträger, Frank'
_publ_section_title
;
 A short survey of bicyclic diamines -- syntheses and
 properties of N,N'-bridged-1,10-diazabicyclooctadeca-5,14-diynes
;
_journal_issue                   2
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              175
_journal_paper_doi               10.1039/a907609c
_journal_year                    2000
_chemical_formula_sum            'C20 H40 N2 O5'
_chemical_formula_weight         388.54
_chemical_name_systematic
;
 1,10-Diaza-21-oxabicyclo[8.8.5]tricosa-5,14-diyne (43)
;
_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           SHELXL-97
_cell_angle_alpha                104.35(3)
_cell_angle_beta                 94.56(3)
_cell_angle_gamma                99.02(3)
_cell_formula_units_Z            4
_cell_length_a                   8.899(3)
_cell_length_b                   12.364(4)
_cell_length_c                   20.155(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      17.07
_cell_measurement_theta_min      10.05
_cell_volume                     2105.5(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  NONIUS_CAD4
_diffrn_measurement_method       ω2θ
_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  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0487
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10779
_diffrn_reflns_theta_full        27.98
_diffrn_reflns_theta_max         27.98
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        4
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9744
_exptl_absorpt_correction_T_min  0.9661
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    ride
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         10134
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1190
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.109
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1142P)²+0.1755P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1590
_refine_ls_wR_factor_ref         0.1878
_reflns_number_gt                6036
_reflns_number_total             10134
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            a907609c.txt
_cod_data_source_block           744hbo
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1142P)^2^+0.1755P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1142P)^2^+0.1755P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               7203902
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.09502(16) 0.22851(12) 0.32761(7) 0.0288(3) Uani 1 d . . .
N1A N 0.14614(19) 0.13332(13) 0.87310(9) 0.0402(4) Uani 1 d . . .
N10 N 0.06922(18) 0.32425(12) 0.59220(8) 0.0342(3) Uani 1 d . . .
N10A N 0.2313(2) 0.54645(14) 0.84202(10) 0.0459(4) Uani 1 d . . .
O21 O 0.17445(14) 0.39792(10) 0.46597(6) 0.0346(3) Uani 1 d . . .
O21A O 0.0165(2) 0.32876(17) 0.83727(12) 0.0385(4) Uani 0.75 d P A 3
O21B O 0.0337(10) 0.3091(7) 0.8084(4) 0.053(2) Uiso 0.25 d P A 4
C2 C 0.1155(2) 0.13546(15) 0.35902(9) 0.0306(4) Uani 1 d . . .
H2A H 0.0240 0.0757 0.3444 0.037 Uiso 1 calc R . .
H2B H 0.1243 0.1642 0.4093 0.037 Uiso 1 calc R . .
C2A C 0.2122(3) 0.22331(18) 0.93557(11) 0.0456(5) Uani 1 d . . .
H2C H 0.2019 0.2967 0.9272 0.055 Uiso 1 calc R . .
H2D H 0.3220 0.2226 0.9439 0.055 Uiso 1 calc R . .
C3 C 0.2554(2) 0.08400(16) 0.34021(10) 0.0348(4) Uani 1 d . . .
H3A H 0.3478 0.1424 0.3569 0.042 Uiso 1 calc R . .
H3B H 0.2493 0.0577 0.2899 0.042 Uiso 1 calc R . .
C3A C 0.1411(4) 0.2142(2) 0.99972(14) 0.0713(8) Uani 1 d . . .
H3C H 0.1368 0.1370 1.0048 0.086 Uiso 1 calc R . .
H3D H 0.0358 0.2280 0.9950 0.086 Uiso 1 calc R . .
C4 C 0.2681(2) -0.01568(16) 0.37133(10) 0.0393(4) Uani 1 d . . .
H4A H 0.1790 -0.0761 0.3520 0.047 Uiso 1 calc R . .
H4B H 0.3600 -0.0459 0.3580 0.047 Uiso 1 calc R . .
C4A C 0.2315(4) 0.2991(2) 1.06433(13) 0.0742(9) Uani 1 d . . .
H4C H 0.1786 0.2927 1.1044 0.089 Uiso 1 calc R . .
H4D H 0.3331 0.2798 1.0718 0.089 Uiso 1 calc R . .
C5 C 0.2764(2) 0.01542(15) 0.44657(10) 0.0355(4) Uani 1 d . . .
C5A C 0.2497(3) 0.4167(2) 1.05933(11) 0.0526(6) Uani 1 d . . .
C6 C 0.2796(2) 0.04004(15) 0.50758(10) 0.0354(4) Uani 1 d . . .
C6A C 0.2652(3) 0.5094(2) 1.05318(12) 0.0568(6) Uani 1 d . . .
C7 C 0.2783(2) 0.07246(16) 0.58261(10) 0.0385(4) Uani 1 d . . .
H7A H 0.3793 0.1158 0.6048 0.046 Uiso 1 calc R . .
H7B H 0.2591 0.0037 0.5988 0.046 Uiso 1 calc R . .
C7A C 0.2801(4) 0.6218(2) 1.04021(15) 0.0827(10) Uani 1 d . . .
H7C H 0.3888 0.6568 1.0473 0.099 Uiso 1 calc R B 1
H7D H 0.2278 0.6700 1.0735 0.099 Uiso 1 calc R B 1
C8 C 0.1553(2) 0.14430(16) 0.60413(10) 0.0384(4) Uani 1 d . . .
H8A H 0.0541 0.1018 0.5818 0.046 Uiso 1 calc R . .
H8B H 0.1545 0.1608 0.6542 0.046 Uiso 1 calc R . .
C9 C 0.1888(2) 0.25481(15) 0.58319(9) 0.0333(4) Uani 1 d . . .
H9A H 0.2844 0.3002 0.6102 0.040 Uiso 1 calc R . .
H9B H 0.2058 0.2369 0.5345 0.040 Uiso 1 calc R . .
C8A C 0.2097(9) 0.6160(5) 0.9644(3) 0.0544(13) Uani 0.50 d P C 1
H8C H 0.0994 0.5861 0.9585 0.065 Uiso 0.50 calc PR C 1
H8D H 0.2234 0.6929 0.9581 0.065 Uiso 0.50 calc PR C 1
C9A C 0.2868(5) 0.5384(4) 0.9073(2) 0.0337(8) Uani 0.50 d P C 1
H9C H 0.3984 0.5630 0.9155 0.040 Uiso 0.50 calc PR C 1
H9D H 0.2631 0.4594 0.9095 0.040 Uiso 0.50 calc PR C 1
C8B C 0.3042(8) 0.6245(5) 0.9750(3) 0.0585(15) Uani 0.50 d P C 2
H8E H 0.4067 0.6075 0.9681 0.070 Uiso 0.50 calc PR C 2
H8F H 0.3059 0.7025 0.9718 0.070 Uiso 0.50 calc PR C 2
C9B C 0.1987(9) 0.5505(5) 0.9188(3) 0.0670(15) Uani 0.50 d P C 2
H9E H 0.0976 0.5713 0.9240 0.080 Uiso 0.50 calc PR C 2
H9F H 0.1912 0.4732 0.9241 0.080 Uiso 0.50 calc PR C 2
C11 C -0.0726(2) 0.27066(15) 0.54550(9) 0.0346(4) Uani 1 d . . .
H11A H -0.0901 0.1886 0.5406 0.041 Uiso 1 calc R . .
H11B H -0.0604 0.2827 0.4998 0.041 Uiso 1 calc R . .
C12 C -0.2117(2) 0.31717(18) 0.57096(10) 0.0406(4) Uani 1 d . . .
H12A H -0.2003 0.3969 0.5701 0.049 Uiso 1 calc R . .
H12B H -0.2163 0.3142 0.6189 0.049 Uiso 1 calc R . .
C11A C 0.3080(4) 0.4760(3) 0.7854(2) 0.0287(7) Uani 0.50 d P C 1
H11C H 0.2604 0.4782 0.7404 0.034 Uiso 0.50 calc PR C 1
H11D H 0.2890 0.3968 0.7876 0.034 Uiso 0.50 calc PR C 1
C12A C 0.4827(6) 0.5173(5) 0.7910(3) 0.0394(13) Uani 0.50 d P C 1
H12C H 0.5022 0.5914 0.7808 0.047 Uiso 0.50 calc PR C 1
H12D H 0.5292 0.5267 0.8383 0.047 Uiso 0.50 calc PR C 1
C11B C 0.3495(6) 0.4806(4) 0.8304(3) 0.0592(12) Uani 0.50 d P C 2
H11E H 0.3067 0.4006 0.8252 0.071 Uiso 0.50 calc PR C 2
H11F H 0.4290 0.5058 0.8703 0.071 Uiso 0.50 calc PR C 2
C12B C 0.4178(12) 0.4929(6) 0.7679(4) 0.071(2) Uani 0.50 d P C 2
H12E H 0.4500 0.5745 0.7737 0.086 Uiso 0.50 calc PR C 2
H12F H 0.3345 0.4665 0.7297 0.086 Uiso 0.50 calc PR C 2
C13 C -0.3622(2) 0.25096(18) 0.52727(11) 0.0406(4) Uani 1 d . . .
H13A H -0.3822 0.1749 0.5347 0.049 Uiso 1 calc R . .
H13B H -0.4463 0.2893 0.5431 0.049 Uiso 1 calc R . .
C13A C 0.5532(3) 0.4367(2) 0.74303(15) 0.0617(7) Uani 1 d . . .
H13C H 0.6634 0.4670 0.7485 0.074 Uiso 1 calc R D 1
H13D H 0.5119 0.4342 0.6960 0.074 Uiso 1 calc R D 1
C14 C -0.3616(2) 0.24001(15) 0.45281(10) 0.0344(4) Uani 1 d . . .
C14A C 0.5342(2) 0.31936(19) 0.74906(12) 0.0464(5) Uani 1 d . . .
C15 C -0.3561(2) 0.23220(15) 0.39330(10) 0.0342(4) Uani 1 d . . .
C15A C 0.5150(2) 0.22602(18) 0.75575(11) 0.0426(5) Uani 1 d . . .
C16 C -0.3394(2) 0.22104(17) 0.32015(10) 0.0381(4) Uani 1 d . . .
H16A H -0.3391 0.2948 0.3102 0.046 Uiso 1 calc R . .
H16B H -0.4271 0.1672 0.2915 0.046 Uiso 1 calc R . .
C16A C 0.4855(2) 0.11121(17) 0.76636(11) 0.0435(5) Uani 1 d . . .
H16C H 0.5838 0.0875 0.7747 0.052 Uiso 1 calc R . .
H16D H 0.4288 0.0581 0.7241 0.052 Uiso 1 calc R . .
C17 C -0.1912(2) 0.17973(16) 0.30161(10) 0.0365(4) Uani 1 d . . .
H17A H -0.1896 0.1074 0.3131 0.044 Uiso 1 calc R . .
H17B H -0.1876 0.1668 0.2518 0.044 Uiso 1 calc R . .
C17A C 0.3947(2) 0.10434(18) 0.82651(11) 0.0427(5) Uani 1 d . . .
H17C H 0.3818 0.0269 0.8319 0.051 Uiso 1 calc R . .
H17D H 0.4524 0.1557 0.8691 0.051 Uiso 1 calc R . .
C18 C -0.0524(2) 0.26573(15) 0.34023(9) 0.0313(4) Uani 1 d . . .
H18A H -0.0528 0.3366 0.3268 0.038 Uiso 1 calc R . .
H18B H -0.0606 0.2818 0.3898 0.038 Uiso 1 calc R . .
C18A C 0.2387(2) 0.13577(17) 0.81576(10) 0.0400(4) Uani 1 d . . .
H18C H 0.2527 0.2123 0.8089 0.048 Uiso 1 calc R . .
H18D H 0.1815 0.0833 0.7735 0.048 Uiso 1 calc R . .
C19 C 0.2247(2) 0.32498(16) 0.34805(10) 0.0367(4) Uani 1 d . . .
H19A H 0.1925 0.3884 0.3331 0.044 Uiso 1 calc R . .
H19B H 0.3085 0.3032 0.3219 0.044 Uiso 1 calc R . .
C19A C -0.0157(2) 0.13543(19) 0.85086(14) 0.0550(6) Uani 1 d . . .
H19C H -0.0661 0.1562 0.8925 0.066 Uiso 1 calc R E 3
H19D H -0.0648 0.0578 0.8258 0.066 Uiso 1 calc R E 3
C20 C 0.2892(2) 0.36868(17) 0.42310(11) 0.0396(4) Uani 1 d . . .
H20A H 0.3365 0.3103 0.4374 0.048 Uiso 1 calc R . .
H20B H 0.3692 0.4357 0.4291 0.048 Uiso 1 calc R . .
C20A C -0.0491(3) 0.2124(2) 0.80651(18) 0.0447(7) Uani 0.75 d P A 3
H20C H -0.0095 0.1875 0.7623 0.054 Uiso 0.75 calc PR A 3
H20D H -0.1604 0.2053 0.7970 0.054 Uiso 0.75 calc PR A 3
C20B C -0.0598(15) 0.2417(12) 0.8412(7) 0.068(3) Uiso 0.25 d P A 4
H20E H -0.1623 0.2215 0.8150 0.082 Uiso 0.25 calc PR A 4
H20F H -0.0690 0.2893 0.8869 0.082 Uiso 0.25 calc PR A 4
C22 C 0.2397(2) 0.45282(15) 0.53523(10) 0.0393(4) Uani 1 d . . .
H22A H 0.2738 0.5339 0.5396 0.047 Uiso 1 calc R . .
H22B H 0.3298 0.4210 0.5462 0.047 Uiso 1 calc R . .
C22A C -0.0093(3) 0.3961(2) 0.79159(15) 0.0702(8) Uani 1 d . . .
H22C H -0.1194 0.3967 0.7852 0.084 Uiso 1 calc R F 3
H22D H 0.0191 0.3591 0.7466 0.084 Uiso 1 calc R F 3
C23 C 0.1272(2) 0.43913(15) 0.58635(10) 0.0397(4) Uani 1 d . . .
H23A H 0.1761 0.4851 0.6321 0.048 Uiso 1 calc R . .
H23B H 0.0386 0.4719 0.5746 0.048 Uiso 1 calc R . .
C23A C 0.0720(3) 0.5130(2) 0.81220(17) 0.0733(8) Uani 1 d . . .
H23C H 0.0636 0.5418 0.7712 0.088 Uiso 1 calc R . .
H23D H 0.0134 0.5555 0.8453 0.088 Uiso 1 calc R . .
O1 O 0.1471(2) -0.07908(13) 0.90007(9) 0.0519(4) Uani 1 d . . .
H1A H 0.150(3) -0.006(2) 0.8940(13) 0.062 Uiso 1 d . . .
H1B H 0.188(3) -0.061(2) 0.9405(15) 0.062 Uiso 1 d . . .
O2 O 0.1155(2) 0.18828(16) 0.18603(8) 0.0586(5) Uani 1 d . . .
H2E H 0.105(3) 0.192(2) 0.2249(16) 0.070 Uiso 1 d . . .
H2F H -0.021(3) 0.133(2) 0.1381(14) 0.070 Uiso 1 d . . .
O3 O 0.3535(2) 0.77534(16) 0.85009(11) 0.0650(5) Uani 1 d . . .
H3E H 0.299(3) 0.701(3) 0.8375(15) 0.078 Uiso 1 d . . .
H3F H 0.280(4) 0.812(3) 0.8596(16) 0.078 Uiso 1 d . . .
O4 O 0.3688(2) 0.09316(18) 0.15894(11) 0.0658(5) Uani 1 d . . .
H4E H 0.351(4) 0.059(3) 0.1174(17) 0.079 Uiso 1 d . . .
H4F H 0.446(4) 0.139(3) 0.1566(16) 0.079 Uiso 1 d . . .
O5 O 0.3593(8) -0.0538(8) 0.0200(4) 0.085(2) Uani 0.50 d P . .
O5A O 0.2910(8) -0.0512(8) 0.0316(4) 0.093(2) Uani 0.50 d P . .
O6 O 0.5065(8) -0.1494(5) -0.0125(3) 0.0544(15) Uiso 0.25 d P . .
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'
O O 0.0106 0.0060 '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'
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
C2 N1 C19 113.37(14) . . ?
C2 N1 C18 111.44(13) . . ?
C19 N1 C18 111.58(14) . . ?
C2A N1A C18A 111.79(16) . . ?
C2A N1A C19A 113.11(17) . . ?
C18A N1A C19A 110.27(17) . . ?
C9 N10 C11 112.76(14) . . ?
C9 N10 C23 110.69(15) . . ?
C11 N10 C23 111.97(15) . . ?
C9A N10A C11B 74.6(3) . . ?
C9A N10A C23A 124.4(3) . . ?
C11B N10A C23A 127.1(3) . . ?
C9A N10A C11A 111.0(3) . . ?
C11B N10A C11A 36.7(3) . . ?
C23A N10A C11A 100.8(2) . . ?
C9A N10A C9B 32.7(3) . . ?
C11B N10A C9B 104.7(4) . . ?
C23A N10A C9B 95.5(3) . . ?
C11A N10A C9B 138.3(3) . . ?
C20 O21 C22 111.40(14) . . ?
C22A O21A C20A 111.0(2) . . ?
C22A O21B C20B 121.6(8) . . ?
N1 C2 C3 113.66(14) . . ?
N1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
N1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
N1A C2A C3A 115.02(19) . . ?
N1A C2A H2C 108.5 . . ?
C3A C2A H2C 108.5 . . ?
N1A C2A H2D 108.5 . . ?
C3A C2A H2D 108.5 . . ?
H2C C2A H2D 107.5 . . ?
C2 C3 C4 111.84(15) . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C2A C3A C4A 111.9(2) . . ?
C2A C3A H3C 109.2 . . ?
C4A C3A H3C 109.2 . . ?
C2A C3A H3D 109.2 . . ?
C4A C3A H3D 109.2 . . ?
H3C C3A H3D 107.9 . . ?
C5 C4 C3 113.15(15) . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.8 . . ?
C5A C4A C3A 112.6(2) . . ?
C5A C4A H4C 109.1 . . ?
C3A C4A H4C 109.1 . . ?
C5A C4A H4D 109.1 . . ?
C3A C4A H4D 109.1 . . ?
H4C C4A H4D 107.8 . . ?
C6 C5 C4 178.5(2) . . ?
C6A C5A C4A 177.8(2) . . ?
C5 C6 C7 177.8(2) . . ?
C5A C6A C7A 175.8(3) . . ?
C6 C7 C8 112.17(15) . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C8B C7A C6A 115.1(3) . . ?
C8B C7A C8A 31.8(3) . . ?
C6A C7A C8A 112.2(3) . . ?
C8B C7A H7C 79.0 . . ?
C6A C7A H7C 109.2 . . ?
C8A C7A H7C 109.2 . . ?
C8B C7A H7D 129.8 . . ?
C6A C7A H7D 109.2 . . ?
C8A C7A H7D 109.2 . . ?
H7C C7A H7D 107.9 . . ?
C9 C8 C7 109.92(16) . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N10 C9 C8 115.43(16) . . ?
N10 C9 H9A 108.4 . . ?
C8 C9 H9A 108.4 . . ?
N10 C9 H9B 108.4 . . ?
C8 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
C9A C8A C7A 112.4(4) . . ?
C9A C8A H8C 109.1 . . ?
C7A C8A H8C 109.1 . . ?
C9A C8A H8D 109.1 . . ?
C7A C8A H8D 109.1 . . ?
H8C C8A H8D 107.9 . . ?
N10A C9A C8A 109.5(4) . . ?
N10A C9A H9C 109.8 . . ?
C8A C9A H9C 109.8 . . ?
N10A C9A H9D 109.8 . . ?
C8A C9A H9D 109.8 . . ?
H9C C9A H9D 108.2 . . ?
C7A C8B C9B 118.5(6) . . ?
C7A C8B H8E 107.7 . . ?
C9B C8B H8E 107.7 . . ?
C7A C8B H8F 107.7 . . ?
C9B C8B H8F 107.7 . . ?
H8E C8B H8F 107.1 . . ?
C8B C9B N10A 119.1(5) . . ?
C8B C9B H9E 107.5 . . ?
N10A C9B H9E 107.5 . . ?
C8B C9B H9F 107.5 . . ?
N10A C9B H9F 107.5 . . ?
H9E C9B H9F 107.0 . . ?
N10 C11 C12 112.71(15) . . ?
N10 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
N10 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C13 112.60(16) . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
N10A C11A C12A 113.7(3) . . ?
N10A C11A H11C 108.8 . . ?
C12A C11A H11C 108.8 . . ?
N10A C11A H11D 108.8 . . ?
C12A C11A H11D 108.8 . . ?
H11C C11A H11D 107.7 . . ?
C13A C12A C11A 111.1(4) . . ?
C13A C12A H12C 109.4 . . ?
C11A C12A H12C 109.4 . . ?
C13A C12A H12D 109.4 . . ?
C11A C12A H12D 109.4 . . ?
H12C C12A H12D 108.0 . . ?
N10A C11B C12B 110.5(5) . . ?
N10A C11B H11E 109.5 . . ?
C12B C11B H11E 109.5 . . ?
N10A C11B H11F 109.5 . . ?
C12B C11B H11F 109.5 . . ?
H11E C11B H11F 108.1 . . ?
C11B C12B C13A 123.3(5) . . ?
C11B C12B H12E 106.5 . . ?
C13A C12B H12E 106.5 . . ?
C11B C12B H12F 106.5 . . ?
C13A C12B H12F 106.5 . . ?
H12E C12B H12F 106.5 . . ?
C14 C13 C12 113.59(17) . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C12A C13A C14A 117.8(3) . . ?
C12A C13A C12B 26.3(3) . . ?
C14A C13A C12B 111.2(4) . . ?
C12A C13A H13C 107.9 . . ?
C14A C13A H13C 107.9 . . ?
C12B C13A H13C 131.3 . . ?
C12A C13A H13D 107.9 . . ?
C14A C13A H13D 107.9 . . ?
C12B C13A H13D 87.3 . . ?
H13C C13A H13D 107.2 . . ?
C15 C14 C13 177.88(19) . . ?
C15A C14A C13A 177.4(2) . . ?
C14 C15 C16 176.35(19) . . ?
C14A C15A C16A 177.3(2) . . ?
C15 C16 C17 111.38(15) . . ?
C15 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C15A C16A C17A 113.06(17) . . ?
C15A C16A H16C 109.0 . . ?
C17A C16A H16C 109.0 . . ?
C15A C16A H16D 109.0 . . ?
C17A C16A H16D 109.0 . . ?
H16C C16A H16D 107.8 . . ?
C18 C17 C16 110.95(15) . . ?
C18 C17 H17A 109.4 . . ?
C16 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C18A C17A C16A 111.81(18) . . ?
C18A C17A H17C 109.3 . . ?
C16A C17A H17C 109.3 . . ?
C18A C17A H17D 109.3 . . ?
C16A C17A H17D 109.3 . . ?
H17C C17A H17D 107.9 . . ?
N1 C18 C17 113.85(15) . . ?
N1 C18 H18A 108.8 . . ?
C17 C18 H18A 108.8 . . ?
N1 C18 H18B 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
N1A C18A C17A 114.51(17) . . ?
N1A C18A H18C 108.6 . . ?
C17A C18A H18C 108.6 . . ?
N1A C18A H18D 108.6 . . ?
C17A C18A H18D 108.6 . . ?
H18C C18A H18D 107.6 . . ?
N1 C19 C20 118.65(16) . . ?
N1 C19 H19A 107.7 . . ?
C20 C19 H19A 107.7 . . ?
N1 C19 H19B 107.7 . . ?
C20 C19 H19B 107.7 . . ?
H19A C19 H19B 107.1 . . ?
N1A C19A C20B 120.0(6) . . ?
N1A C19A C20A 118.7(2) . . ?
C20B C19A C20A 28.1(5) . . ?
N1A C19A H19C 107.6 . . ?
C20B C19A H19C 81.4 . . ?
C20A C19A H19C 107.6 . . ?
N1A C19A H19D 107.6 . . ?
C20B C19A H19D 126.5 . . ?
C20A C19A H19D 107.6 . . ?
H19C C19A H19D 107.1 . . ?
O21 C20 C19 112.03(15) . . ?
O21 C20 H20A 109.2 . . ?
C19 C20 H20A 109.2 . . ?
O21 C20 H20B 109.2 . . ?
C19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
O21A C20A C19A 113.4(2) . . ?
O21A C20A H20C 108.9 . . ?
C19A C20A H20C 108.9 . . ?
O21A C20A H20D 108.9 . . ?
C19A C20A H20D 108.9 . . ?
H20C C20A H20D 107.7 . . ?
O21B C20B C19A 119.6(10) . . ?
O21B C20B H20E 107.4 . . ?
C19A C20B H20E 107.4 . . ?
O21B C20B H20F 107.4 . . ?
C19A C20B H20F 107.4 . . ?
H20E C20B H20F 107.0 . . ?
O21 C22 C23 112.21(15) . . ?
O21 C22 H22A 109.2 . . ?
C23 C22 H22A 109.2 . . ?
O21 C22 H22B 109.2 . . ?
C23 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
O21B C22A O21A 25.7(3) . . ?
O21B C22A C23A 127.1(4) . . ?
O21A C22A C23A 116.5(2) . . ?
O21B C22A H22C 117.8 . . ?
O21A C22A H22C 108.2 . . ?
C23A C22A H22C 108.2 . . ?
O21B C22A H22D 82.5 . . ?
O21A C22A H22D 108.2 . . ?
C23A C22A H22D 108.2 . . ?
H22C C22A H22D 107.3 . . ?
N10 C23 C22 118.49(15) . . ?
N10 C23 H23A 107.7 . . ?
C22 C23 H23A 107.7 . . ?
N10 C23 H23B 107.7 . . ?
C22 C23 H23B 107.7 . . ?
H23A C23 H23B 107.1 . . ?
N10A C23A C22A 123.6(2) . . ?
N10A C23A H23C 106.4 . . ?
C22A C23A H23C 106.4 . . ?
N10A C23A H23D 106.4 . . ?
C22A C23A H23D 106.4 . . ?
H23C C23A H23D 106.5 . . ?
H1A O1 H1B 99(2) . . ?
H2E O2 H2F 114(2) . . ?
H3E O3 H3F 100(3) . . ?
H4E O4 H4F 97(3) . . ?
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 C2 1.472(2) . ?
N1 C19 1.474(2) . ?
N1 C18 1.477(2) . ?
N1A C2A 1.467(3) . ?
N1A C18A 1.475(3) . ?
N1A C19A 1.480(3) . ?
N10 C9 1.464(2) . ?
N10 C11 1.469(2) . ?
N10 C23 1.470(2) . ?
N10A C9A 1.400(4) . ?
N10A C11B 1.426(5) . ?
N10A C23A 1.449(3) . ?
N10A C11A 1.531(4) . ?
N10A C9B 1.587(7) . ?
O21 C20 1.421(2) . ?
O21 C22 1.423(2) . ?
O21A C22A 1.414(3) . ?
O21A C20A 1.425(4) . ?
O21B C22A 1.307(8) . ?
O21B C20B 1.401(15) . ?
C2 C3 1.517(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2A C3A 1.505(3) . ?
C2A H2C 0.9800 . ?
C2A H2D 0.9800 . ?
C3 C4 1.530(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3A C4A 1.528(4) . ?
C3A H3C 0.9800 . ?
C3A H3D 0.9800 . ?
C4 C5 1.462(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4A C5A 1.468(3) . ?
C4A H4C 0.9800 . ?
C4A H4D 0.9800 . ?
C5 C6 1.188(3) . ?
C5A C6A 1.171(3) . ?
C6 C7 1.467(3) . ?
C6A C7A 1.465(4) . ?
C7 C8 1.537(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7A C8B 1.356(7) . ?
C7A C8A 1.585(7) . ?
C7A H7C 0.9800 . ?
C7A H7D 0.9800 . ?
C8 C9 1.521(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C8A C9A 1.581(7) . ?
C8A H8C 0.9800 . ?
C8A H8D 0.9800 . ?
C9A H9C 0.9800 . ?
C9A H9D 0.9800 . ?
C8B C9B 1.432(9) . ?
C8B H8E 0.9800 . ?
C8B H8F 0.9800 . ?
C9B H9E 0.9800 . ?
C9B H9F 0.9800 . ?
C11 C12 1.518(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 C13 1.533(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C11A C12A 1.545(6) . ?
C11A H11C 0.9800 . ?
C11A H11D 0.9800 . ?
C12A C13A 1.461(7) . ?
C12A H12C 0.9800 . ?
C12A H12D 0.9800 . ?
C11B C12B 1.472(9) . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B C13A 1.539(9) . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
C13 C14 1.474(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13A C14A 1.471(3) . ?
C13A H13C 0.9800 . ?
C13A H13D 0.9800 . ?
C14 C15 1.185(3) . ?
C14A C15A 1.182(3) . ?
C15 C16 1.468(3) . ?
C15A C16A 1.474(3) . ?
C16 C17 1.527(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16A C17A 1.521(3) . ?
C16A H16C 0.9800 . ?
C16A H16D 0.9800 . ?
C17 C18 1.512(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17A C18A 1.513(3) . ?
C17A H17C 0.9800 . ?
C17A H17D 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C18A H18D 0.9800 . ?
C19 C20 1.506(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19A C20B 1.481(13) . ?
C19A C20A 1.504(4) . ?
C19A H19C 0.9800 . ?
C19A H19D 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20A H20C 0.9800 . ?
C20A H20D 0.9800 . ?
C20B H20E 0.9800 . ?
C20B H20F 0.9800 . ?
C22 C23 1.513(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22A C23A 1.454(4) . ?
C22A H22C 0.9800 . ?
C22A H22D 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23A H23C 0.9800 . ?
C23A H23D 0.9800 . ?
O1 H1A 0.94(3) . ?
O1 H1B 0.83(3) . ?
O2 H2E 0.79(3) . ?
O2 H2F 1.45(3) . ?
O3 H3E 0.94(3) . ?
O3 H3F 0.86(3) . ?
O4 H4E 0.83(3) . ?
O4 H4F 0.83(3) . ?
O5 O5A 0.671(7) . ?
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
C19 N1 C2 C3 -60.3(2) . . . . ?
C18 N1 C2 C3 172.79(14) . . . . ?
C18A N1A C2A C3A -169.7(2) . . . . ?
C19A N1A C2A C3A 65.2(3) . . . . ?
N1 C2 C3 C4 -177.45(15) . . . . ?
N1A C2A C3A C4A 171.0(2) . . . . ?
C2 C3 C4 C5 -58.4(2) . . . . ?
C2A C3A C4A C5A 56.1(3) . . . . ?
C3 C4 C5 C6 91(7) . . . . ?
C3A C4A C5A C6A -43(8) . . . . ?
C4 C5 C6 C7 -41(11) . . . . ?
C4A C5A C6A C7A 33(11) . . . . ?
C5 C6 C7 C8 -5(5) . . . . ?
C5A C6A C7A C8B -30(4) . . . . ?
C5A C6A C7A C8A 5(4) . . . . ?
C6 C7 C8 C9 -62.3(2) . . . . ?
C11 N10 C9 C8 -67.1(2) . . . . ?
C23 N10 C9 C8 166.61(15) . . . . ?
C7 C8 C9 N10 172.02(15) . . . . ?
C8B C7A C8A C9A 44.0(6) . . . . ?
C6A C7A C8A C9A -58.2(6) . . . . ?
C11B N10A C9A C8A 173.5(4) . . . . ?
C23A N10A C9A C8A -61.8(4) . . . . ?
C11A N10A C9A C8A 177.8(4) . . . . ?
C9B N10A C9A C8A -30.4(5) . . . . ?
C7A C8A C9A N10A -173.8(4) . . . . ?
C6A C7A C8B C9B 54.2(8) . . . . ?
C8A C7A C8B C9B -37.9(6) . . . . ?
C7A C8B C9B N10A -175.9(4) . . . . ?
C9A N10A C9B C8B 52.7(6) . . . . ?
C11B N10A C9B C8B 76.5(6) . . . . ?
C23A N10A C9B C8B -152.8(6) . . . . ?
C11A N10A C9B C8B 94.3(6) . . . . ?
C9 N10 C11 C12 158.71(16) . . . . ?
C23 N10 C11 C12 -75.7(2) . . . . ?
N10 C11 C12 C13 -172.66(16) . . . . ?
C9A N10A C11A C12A -63.4(4) . . . . ?
C11B N10A C11A C12A -56.3(5) . . . . ?
C23A N10A C11A C12A 163.0(3) . . . . ?
C9B N10A C11A C12A -85.9(6) . . . . ?
N10A C11A C12A C13A 170.7(3) . . . . ?
C9A N10A C11B C12B -153.1(6) . . . . ?
C23A N10A C11B C12B 85.1(6) . . . . ?
C11A N10A C11B C12B 33.8(5) . . . . ?
C9B N10A C11B C12B -166.1(5) . . . . ?
N10A C11B C12B C13A 177.2(6) . . . . ?
C11 C12 C13 C14 -52.9(2) . . . . ?
C11A C12A C13A C14A -57.9(5) . . . . ?
C11A C12A C13A C12B 23.9(7) . . . . ?
C11B C12B C13A C12A -67.6(10) . . . . ?
C11B C12B C13A C14A 42.5(9) . . . . ?
C12 C13 C14 C15 16(5) . . . . ?
C12A C13A C14A C15A 8(6) . . . . ?
C12B C13A C14A C15A -20(6) . . . . ?
C13 C14 C15 C16 27(8) . . . . ?
C13A C14A C15A C16A 2(10) . . . . ?
C14 C15 C16 C17 7(3) . . . . ?
C14A C15A C16A C17A -12(5) . . . . ?
C15 C16 C17 C18 -64.0(2) . . . . ?
C15A C16A C17A C18A 60.8(2) . . . . ?
C2 N1 C18 C17 -69.61(19) . . . . ?
C19 N1 C18 C17 162.54(15) . . . . ?
C16 C17 C18 N1 176.88(15) . . . . ?
C2A N1A C18A C17A 68.0(2) . . . . ?
C19A N1A C18A C17A -165.31(17) . . . . ?
C16A C17A C18A N1A -178.68(16) . . . . ?
C2 N1 C19 C20 -45.8(2) . . . . ?
C18 N1 C19 C20 81.0(2) . . . . ?
C2A N1A C19A C20B 52.6(7) . . . . ?
C18A N1A C19A C20B -73.4(7) . . . . ?
C2A N1A C19A C20A 84.9(3) . . . . ?
C18A N1A C19A C20A -41.1(3) . . . . ?
C22 O21 C20 C19 -172.29(15) . . . . ?
N1 C19 C20 O21 -54.9(2) . . . . ?
C22A O21A C20A C19A 175.9(2) . . . . ?
N1A C19A C20A O21A -57.5(3) . . . . ?
C20B C19A C20A O21A 43.1(11) . . . . ?
C22A O21B C20B C19A 171.9(8) . . . . ?
N1A C19A C20B O21B 42.3(14) . . . . ?
C20A C19A C20B O21B -53.2(10) . . . . ?
C20 O21 C22 C23 -154.99(15) . . . . ?
C20B O21B C22A O21A 49.9(10) . . . . ?
C20B O21B C22A C23A 123.6(9) . . . . ?
C20A O21A C22A O21B -49.4(9) . . . . ?
C20A O21A C22A C23A -170.6(3) . . . . ?
C9 N10 C23 C22 35.8(2) . . . . ?
C11 N10 C23 C22 -90.9(2) . . . . ?
O21 C22 C23 N10 63.2(2) . . . . ?
C9A N10A C23A C22A -67.7(4) . . . . ?
C11B N10A C23A C22A 28.9(5) . . . . ?
C11A N10A C23A C22A 57.3(4) . . . . ?
C9B N10A C23A C22A -84.1(4) . . . . ?
O21B C22A C23A N10A 14.9(7) . . . . ?
O21A C22A C23A N10A 42.5(5) . . . . ?
