#------------------------------------------------------------------------------
#$Date: 2017-12-05 15:22:38 +0200 (Tue, 05 Dec 2017) $
#$Revision: 203995 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/75/1547504.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_1547504
loop_
_publ_author_name
'Danjo, Hiroshi'
'Hamaguchi, Masahiro'
'Asai, Kohei'
'Nakatani, Mizuki'
'Kawanishi, Hiroko'
'Kawahata, Masatoshi'
'Yamaguchi, Kentaro'
_publ_section_title
;
 Proton-Induced Assembly--Disassembly Modulation of Spiroborate Twin-Bowl
 Polymers Bearing Pyridyl Groups
;
_journal_issue                   20
_journal_name_full               Macromolecules
_journal_page_first              8028
_journal_paper_doi               10.1021/acs.macromol.7b01924
_journal_volume                  50
_journal_year                    2017
_chemical_formula_sum            'C114.47 H115.78 B3 N12.82 O14.82'
_chemical_formula_weight         1940.85
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.92(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.269(5)
_cell_length_b                   18.286(4)
_cell_length_c                   33.209(7)
_cell_measurement_reflns_used    21739
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      32.071
_cell_measurement_theta_min      1.595
_cell_volume                     14112(5)
_computing_cell_refinement       HKL2000
_computing_data_collection       HKL2000
_computing_data_reduction        HKL2000
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.878
_diffrn_measured_fraction_theta_max 0.686
_diffrn_measurement_device_type  MX225HE
_diffrn_measurement_method       'phi scans'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.800
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0866
_diffrn_reflns_Laue_measured_fraction_full 0.878
_diffrn_reflns_Laue_measured_fraction_max 0.686
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            21739
_diffrn_reflns_point_group_measured_fraction_full 0.878
_diffrn_reflns_point_group_measured_fraction_max 0.686
_diffrn_reflns_theta_full        28.685
_diffrn_reflns_theta_max         32.071
_diffrn_reflns_theta_min         1.595
_diffrn_source                   'SPring-8 BL38B1'
_exptl_absorpt_coefficient_mu    0.078
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    0.914
_exptl_crystal_description       plate
_exptl_crystal_F_000             4104
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.601
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.286
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     689
_refine_ls_number_reflns         11877
_refine_ls_number_restraints     86
_refine_ls_restrained_S_all      1.290
_refine_ls_R_factor_all          0.1877
_refine_ls_R_factor_gt           0.1230
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3404
_refine_ls_wR_factor_ref         0.3887
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6174
_reflns_number_total             11877
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ma7b01924_si_002.cif
_cod_data_source_block           16A02asi_07_sq
_cod_depositor_comments          'Adding full bibliography for 1547504.cif.'
_cod_database_code               1547504
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.996
_shelx_estimated_absorpt_t_max   0.998
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C 0.45247(15) 0.2040(2) 0.36419(13) 0.0634(11) Uani 1 1 d . . .
C2 C 0.45484(15) 0.2784(2) 0.35821(13) 0.0597(10) Uani 1 1 d . . .
C3 C 0.48091(16) 0.3265(2) 0.38617(14) 0.0652(11) Uani 1 1 d . . .
C4 C 0.50814(18) 0.3032(2) 0.42089(14) 0.0716(12) Uani 1 1 d . . .
H4 H 0.5252 0.3359 0.4393 0.086 Uiso 1 1 calc R U .
C5 C 0.50949(17) 0.2252(2) 0.42790(14) 0.0711(12) Uani 1 1 d . . .
C6 C 0.5394(2) 0.1962(3) 0.46259(15) 0.0847(14) Uani 1 1 d . . .
H6 H 0.5586 0.2280 0.4804 0.102 Uiso 1 1 calc R U .
C7 C 0.5408(2) 0.1221(3) 0.47071(16) 0.0836(14) Uani 1 1 d . . .
C8 C 0.5125(2) 0.0757(3) 0.44343(17) 0.0896(15) Uani 1 1 d . . .
H8 H 0.5132 0.0257 0.4486 0.108 Uiso 1 1 calc R U .
C9 C 0.48334(19) 0.1006(2) 0.40871(16) 0.0789(13) Uani 1 1 d . . .
H9 H 0.4650 0.0677 0.3910 0.095 Uiso 1 1 calc R U .
C10 C 0.48150(16) 0.1771(2) 0.40018(13) 0.0640(11) Uani 1 1 d . . .
C11 C 0.5721(2) 0.0930(4) 0.5066(2) 0.0996(17) Uani 1 1 d . . .
C12 C 0.5691(4) 0.1256(4) 0.5425(3) 0.142(3) Uani 1 1 d . . .
H12 H 0.5467 0.1676 0.5443 0.171 Uiso 1 1 calc R U .
C13 C 0.6291(4) 0.0397(7) 0.5720(4) 0.160(4) Uani 1 1 d . . .
H13 H 0.6517 0.0234 0.5941 0.192 Uiso 1 1 calc R U .
C14 C 0.6319(3) 0.0014(5) 0.5396(3) 0.133(3) Uani 1 1 d . . .
H14 H 0.6525 -0.0423 0.5395 0.159 Uiso 1 1 calc R U .
C15 C 0.6035(3) 0.0273(4) 0.5052(2) 0.123(2) Uani 1 1 d . . .
H15 H 0.6050 0.0015 0.4812 0.148 Uiso 1 1 calc R U .
C16 C 0.42006(16) 0.1530(2) 0.33592(13) 0.0597(10) Uani 1 1 d . . .
C17 C 0.44173(17) 0.1274(2) 0.30201(14) 0.0673(11) Uani 1 1 d . . .
C18 C 0.4143(2) 0.0751(2) 0.27722(16) 0.0775(13) Uani 1 1 d . . .
C19 C 0.36099(19) 0.0486(2) 0.28430(15) 0.0755(12) Uani 1 1 d . . .
H19 H 0.3423 0.0155 0.2669 0.091 Uiso 1 1 calc R U .
C20 C 0.33522(17) 0.0743(2) 0.32002(15) 0.0706(12) Uani 1 1 d . . .
C21 C 0.28054(18) 0.0487(2) 0.33034(16) 0.0755(13) Uani 1 1 d . . .
H21 H 0.2608 0.0163 0.3131 0.091 Uiso 1 1 calc R U .
C22 C 0.25596(17) 0.0702(2) 0.36485(16) 0.0736(12) Uani 1 1 d . . .
C23 C 0.28474(17) 0.1216(3) 0.39002(15) 0.0736(12) Uani 1 1 d . . .
H23 H 0.2678 0.1377 0.4132 0.088 Uiso 1 1 calc R U .
C24 C 0.33759(17) 0.1482(2) 0.38080(14) 0.0674(11) Uani 1 1 d . . .
H24 H 0.3562 0.1817 0.3980 0.081 Uiso 1 1 calc R U .
C25 C 0.36439(16) 0.1254(2) 0.34534(13) 0.0609(10) Uani 1 1 d . . .
C26 C 0.19865(19) 0.0416(3) 0.37584(17) 0.0825(14) Uani 1 1 d . . .
C27 C 0.1888(3) 0.0242(4) 0.4148(2) 0.132(3) Uani 1 1 d . . .
H27 H 0.2182 0.0340 0.4341 0.158 Uiso 1 1 calc R U .
C28 C 0.0975(3) -0.0167(4) 0.3975(3) 0.136(3) Uani 1 1 d . . .
H28 H 0.0634 -0.0388 0.4044 0.163 Uiso 1 1 calc R U .
C29 C 0.1023(2) 0.0023(3) 0.3601(2) 0.1075(19) Uani 1 1 d . . .
H29 H 0.0716 -0.0039 0.3414 0.129 Uiso 1 1 calc R U .
C30 C 0.1533(2) 0.0317(3) 0.34835(19) 0.0954(16) Uani 1 1 d . . .
H30 H 0.1570 0.0450 0.3216 0.114 Uiso 1 1 calc R U .
C31 C 0.46978(13) 0.53216(19) 0.25698(12) 0.0533(9) Uani 1 1 d . . .
C32 C 0.45204(14) 0.4835(2) 0.28521(13) 0.0570(10) Uani 1 1 d . . .
C33 C 0.39682(15) 0.4889(2) 0.30133(13) 0.0588(10) Uani 1 1 d . . .
C34 C 0.35833(15) 0.5408(2) 0.28894(14) 0.0656(11) Uani 1 1 d . . .
H34 H 0.3223 0.5431 0.2998 0.079 Uiso 1 1 calc R U .
C35 C 0.37370(15) 0.5907(2) 0.25947(14) 0.0645(11) Uani 1 1 d . . .
C36 C 0.33617(16) 0.6477(2) 0.24543(15) 0.0708(12) Uani 1 1 d . . .
H36 H 0.2995 0.6502 0.2553 0.085 Uiso 1 1 calc R U .
C37 C 0.35160(17) 0.6985(2) 0.21825(16) 0.0761(13) Uani 1 1 d . . .
C38 C 0.40672(17) 0.6939(2) 0.20295(16) 0.0785(13) Uani 1 1 d . . .
H38 H 0.4178 0.7284 0.1842 0.094 Uiso 1 1 calc R U .
C39 C 0.44389(16) 0.6408(2) 0.21478(15) 0.0710(12) Uani 1 1 d . . .
H39 H 0.4797 0.6391 0.2036 0.085 Uiso 1 1 calc R U .
C40 C 0.43034(14) 0.5875(2) 0.24351(13) 0.0586(10) Uani 1 1 d . . .
C41 C 0.31217(18) 0.7589(3) 0.20490(17) 0.0857(15) Uani 1 1 d . . .
C42 C 0.3315(2) 0.8301(3) 0.2034(3) 0.135(3) Uani 1 1 d . . .
H42 H 0.3700 0.8393 0.2104 0.162 Uiso 1 1 calc R U .
C43 C 0.2433(3) 0.8741(4) 0.1844(3) 0.135(3) Uani 1 1 d . . .
H43 H 0.2191 0.9136 0.1785 0.161 Uiso 1 1 calc R U .
C44 C 0.2199(2) 0.8059(3) 0.18399(19) 0.0994(17) Uani 1 1 d . . .
H44 H 0.1814 0.7988 0.1762 0.119 Uiso 1 1 calc R U .
C45 C 0.25441(19) 0.7480(3) 0.19525(17) 0.0878(15) Uani 1 1 d . . .
H45 H 0.2389 0.7012 0.1964 0.105 Uiso 1 1 calc R U .
B1 B 0.44458(19) 0.3938(3) 0.33335(16) 0.0643(12) Uani 1 1 d . . .
B2 B 0.5000 0.1005(5) 0.2500 0.089(2) Uani 1 2 d S T P
N1 N 0.5986(4) 0.0987(5) 0.5780(2) 0.178(3) Uani 1 1 d . . .
N2 N 0.1399(2) -0.0062(4) 0.4279(2) 0.161(3) Uani 1 1 d . . .
N3 N 0.2975(2) 0.8871(3) 0.1924(3) 0.168(3) Uani 1 1 d . . .
O1 O 0.43237(11) 0.31568(14) 0.32580(9) 0.0685(8) Uani 1 1 d . . .
O2 O 0.47463(12) 0.39691(15) 0.37321(9) 0.0732(8) Uani 1 1 d . . .
O3 O 0.49377(12) 0.14588(18) 0.28667(10) 0.0841(10) Uani 1 1 d . . .
O4 O 0.44662(14) 0.05699(19) 0.24592(11) 0.0921(10) Uani 1 1 d . . .
O5 O 0.48142(10) 0.42743(13) 0.30261(9) 0.0636(8) Uani 1 1 d . . .
O6 O 0.39080(11) 0.43772(15) 0.33020(9) 0.0714(8) Uani 1 1 d . . .
C1A C 0.5672(4) 0.3004(5) 0.2739(3) 0.172(3) Uani 1 1 d D . .
H1AA H 0.5709 0.3053 0.2454 0.258 Uiso 1 1 calc R U .
H1AB H 0.5483 0.3428 0.2839 0.258 Uiso 1 1 calc R U .
H1AC H 0.5449 0.2576 0.2792 0.258 Uiso 1 1 calc R U .
C2A C 0.6494(5) 0.2275(6) 0.2811(4) 0.217(5) Uani 1 1 d D . .
H2AA H 0.6238 0.1876 0.2857 0.325 Uiso 1 1 calc R U .
H2AB H 0.6854 0.2194 0.2958 0.325 Uiso 1 1 calc R U .
H2AC H 0.6559 0.2306 0.2528 0.325 Uiso 1 1 calc R U .
C3A C 0.6559(7) 0.3567(7) 0.2808(4) 0.273(8) Uani 1 1 d D . .
H3AA H 0.6637 0.3512 0.2529 0.410 Uiso 1 1 calc R U .
H3AB H 0.6915 0.3611 0.2965 0.410 Uiso 1 1 calc R U .
H3AC H 0.6331 0.3999 0.2842 0.410 Uiso 1 1 calc R U .
C4A C 0.6147(5) 0.2868(8) 0.3375(3) 0.217(5) Uani 1 1 d D . .
H4AA H 0.5870 0.2489 0.3415 0.326 Uiso 1 1 calc R U .
H4AB H 0.6004 0.3323 0.3473 0.326 Uiso 1 1 calc R U .
H4AC H 0.6503 0.2748 0.3519 0.326 Uiso 1 1 calc R U .
N1A N 0.6247(2) 0.2935(3) 0.29407(16) 0.1021(14) Uani 1 1 d D . .
C1B C 0.3672(12) 0.8579(13) 0.3182(6) 0.523(19) Uani 1 1 d D U .
H1BA H 0.3575 0.8621 0.3458 0.785 Uiso 1 1 calc R U .
H1BB H 0.3617 0.9042 0.3049 0.785 Uiso 1 1 calc R U .
H1BC H 0.3429 0.8218 0.3049 0.785 Uiso 1 1 calc R U .
C2B C 0.4492(17) 0.827(2) 0.2789(8) 0.65(2) Uani 1 1 d D U .
H2BA H 0.4888 0.8121 0.2819 0.982 Uiso 1 1 calc R U .
H2BB H 0.4275 0.7896 0.2643 0.982 Uiso 1 1 calc R U .
H2BC H 0.4463 0.8720 0.2644 0.982 Uiso 1 1 calc R U .
C3B C 0.4638(15) 0.8932(15) 0.3351(10) 0.563(18) Uani 1 1 d D U .
H3BA H 0.4515 0.9030 0.3618 0.844 Uiso 1 1 calc R U .
H3BB H 0.5032 0.8774 0.3367 0.844 Uiso 1 1 calc R U .
H3BC H 0.4603 0.9368 0.3191 0.844 Uiso 1 1 calc R U .
C4B C 0.4327(13) 0.7586(12) 0.3328(8) 0.537(19) Uani 1 1 d D U .
H4BA H 0.4187 0.7573 0.3595 0.805 Uiso 1 1 calc R U .
H4BB H 0.4103 0.7260 0.3157 0.805 Uiso 1 1 calc R U .
H4BC H 0.4723 0.7437 0.3338 0.805 Uiso 1 1 calc R U .
N1B N 0.4276(12) 0.8355(13) 0.3164(6) 0.552(19) Uani 1 1 d D U .
C1C C 0.1950(7) 0.5626(8) 0.3341(5) 0.168(6) Uani 0.644(9) 1 d D . P
H1C H 0.1912 0.5296 0.3128 0.201 Uiso 0.644(9) 1 calc R U P
C2C C 0.1554(7) 0.6215(10) 0.3920(5) 0.197(7) Uani 0.644(9) 1 d D . P
H2CA H 0.1874 0.6537 0.3887 0.296 Uiso 0.644(9) 1 calc R U P
H2CB H 0.1596 0.5977 0.4177 0.296 Uiso 0.644(9) 1 calc R U P
H2CC H 0.1203 0.6492 0.3904 0.296 Uiso 0.644(9) 1 calc R U P
C3C C 0.1031(5) 0.5233(10) 0.3516(4) 0.171(6) Uani 0.644(9) 1 d D . P
H3CA H 0.1066 0.4975 0.3266 0.257 Uiso 0.644(9) 1 calc R U P
H3CB H 0.0700 0.5547 0.3495 0.257 Uiso 0.644(9) 1 calc R U P
H3CC H 0.0988 0.4888 0.3730 0.257 Uiso 0.644(9) 1 calc R U P
N1C N 0.1538(4) 0.5664(5) 0.3600(3) 0.132(3) Uani 0.644(9) 1 d D . P
O1C O 0.2377(6) 0.6008(9) 0.3371(5) 0.255(8) Uani 0.644(9) 1 d D . P
C1D C 0.2379(14) 0.6433(14) 0.5262(11) 0.47(2) Uani 0.692(17) 1 d D U P
H1D H 0.2000 0.6339 0.5321 0.563 Uiso 0.692(17) 1 calc R U P
C2D C 0.3303(10) 0.6868(14) 0.5484(11) 0.392(19) Uani 0.692(17) 1 d D U P
H2DA H 0.3489 0.7084 0.5720 0.588 Uiso 0.692(17) 1 calc R U P
H2DB H 0.3490 0.6415 0.5425 0.588 Uiso 0.692(17) 1 calc R U P
H2DC H 0.3329 0.7196 0.5260 0.588 Uiso 0.692(17) 1 calc R U P
C3D C 0.2498(16) 0.688(2) 0.5945(11) 0.47(2) Uani 0.692(17) 1 d D U P
H3DA H 0.2803 0.7094 0.6109 0.712 Uiso 0.692(17) 1 calc R U P
H3DB H 0.2179 0.7211 0.5921 0.712 Uiso 0.692(17) 1 calc R U P
H3DC H 0.2377 0.6432 0.6066 0.712 Uiso 0.692(17) 1 calc R U P
N1D N 0.2695(10) 0.6729(11) 0.5557(10) 0.404(18) Uani 0.692(17) 1 d D U P
O1D O 0.2503(19) 0.6259(17) 0.4920(11) 0.57(3) Uani 0.692(17) 1 d D U P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0047 0.0022 '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'
B B 0.0021 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0089 0.0045 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0150 0.0081 '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
C2 C1 C10 116.1(4) . .
C2 C1 C16 123.2(4) . .
C10 C1 C16 120.7(3) . .
O1 C2 C1 126.5(4) . .
O1 C2 C3 110.5(3) . .
C1 C2 C3 123.1(4) . .
C4 C3 O2 127.1(4) . .
C4 C3 C2 122.5(4) . .
O2 C3 C2 110.4(4) . .
C3 C4 C5 116.9(4) . .
C3 C4 H4 121.6 . .
C5 C4 H4 121.6 . .
C10 C5 C6 119.3(4) . .
C10 C5 C4 120.3(4) . .
C6 C5 C4 120.4(4) . .
C7 C6 C5 122.1(5) . .
C7 C6 H6 119.0 . .
C5 C6 H6 119.0 . .
C6 C7 C8 117.9(4) . .
C6 C7 C11 121.4(5) . .
C8 C7 C11 120.7(5) . .
C7 C8 C9 122.6(4) . .
C7 C8 H8 118.7 . .
C9 C8 H8 118.7 . .
C8 C9 C10 119.8(4) . .
C8 C9 H9 120.1 . .
C10 C9 H9 120.1 . .
C5 C10 C9 118.3(4) . .
C5 C10 C1 120.9(4) . .
C9 C10 C1 120.8(4) . .
C12 C11 C15 117.4(6) . .
C12 C11 C7 121.0(6) . .
C15 C11 C7 121.5(7) . .
C11 C12 N1 122.6(8) . .
C11 C12 H12 118.7 . .
N1 C12 H12 118.7 . .
C14 C13 N1 128.7(9) . .
C14 C13 H13 115.6 . .
N1 C13 H13 115.6 . .
C13 C14 C15 117.6(9) . .
C13 C14 H14 121.2 . .
C15 C14 H14 121.2 . .
C14 C15 C11 119.8(8) . .
C14 C15 H15 120.1 . .
C11 C15 H15 120.1 . .
C17 C16 C25 116.2(4) . .
C17 C16 C1 123.0(3) . .
C25 C16 C1 120.8(4) . .
C16 C17 O3 126.8(4) . .
C16 C17 C18 123.7(4) . .
O3 C17 C18 109.4(4) . .
O4 C18 C19 126.2(4) . .
O4 C18 C17 111.5(4) . .
C19 C18 C17 122.3(4) . .
C18 C19 C20 116.6(4) . .
C18 C19 H19 121.7 . .
C20 C19 H19 121.7 . .
C25 C20 C21 119.1(4) . .
C25 C20 C19 120.1(4) . .
C21 C20 C19 120.7(4) . .
C22 C21 C20 121.9(4) . .
C22 C21 H21 119.0 . .
C20 C21 H21 119.0 . .
C21 C22 C23 119.0(4) . .
C21 C22 C26 121.4(4) . .
C23 C22 C26 119.5(5) . .
C24 C23 C22 120.7(4) . .
C24 C23 H23 119.7 . .
C22 C23 H23 119.7 . .
C23 C24 C25 121.1(4) . .
C23 C24 H24 119.4 . .
C25 C24 H24 119.4 . .
C20 C25 C24 118.0(3) . .
C20 C25 C16 121.0(4) . .
C24 C25 C16 121.0(4) . .
C27 C26 C30 116.1(5) . .
C27 C26 C22 120.6(5) . .
C30 C26 C22 123.3(5) . .
N2 C27 C26 125.7(6) . .
N2 C27 H27 117.2 . .
C26 C27 H27 117.2 . .
C29 C28 N2 124.4(6) . .
C29 C28 H28 117.8 . .
N2 C28 H28 117.8 . .
C28 C29 C30 119.4(6) . .
C28 C29 H29 120.3 . .
C30 C29 H29 120.3 . .
C26 C30 C29 120.6(6) . .
C26 C30 H30 119.7 . .
C29 C30 H30 119.7 . .
C32 C31 C40 117.7(3) . .
C32 C31 C31 122.0(3) . 2_655
C40 C31 C31 120.1(3) . 2_655
O5 C32 C31 128.6(3) . .
O5 C32 C33 109.9(3) . .
C31 C32 C33 121.5(3) . .
O6 C33 C34 127.6(3) . .
O6 C33 C32 110.3(3) . .
C34 C33 C32 122.1(4) . .
C33 C34 C35 118.8(3) . .
C33 C34 H34 120.6 . .
C35 C34 H34 120.6 . .
C34 C35 C36 122.2(3) . .
C34 C35 C40 120.0(3) . .
C36 C35 C40 117.7(4) . .
C37 C36 C35 122.7(4) . .
C37 C36 H36 118.6 . .
C35 C36 H36 118.6 . .
C36 C37 C38 118.5(4) . .
C36 C37 C41 121.7(4) . .
C38 C37 C41 119.8(4) . .
C39 C38 C37 121.5(4) . .
C39 C38 H38 119.3 . .
C37 C38 H38 119.3 . .
C38 C39 C40 122.2(4) . .
C38 C39 H39 118.9 . .
C40 C39 H39 118.9 . .
C39 C40 C31 122.8(3) . .
C39 C40 C35 117.3(3) . .
C31 C40 C35 119.9(4) . .
C42 C41 C45 116.4(4) . .
C42 C41 C37 120.9(4) . .
C45 C41 C37 122.7(4) . .
N3 C42 C41 123.4(5) . .
N3 C42 H42 118.3 . .
C41 C42 H42 118.3 . .
N3 C43 C44 123.6(5) . .
N3 C43 H43 118.2 . .
C44 C43 H43 118.2 . .
C43 C44 C45 118.6(5) . .
C43 C44 H44 120.7 . .
C45 C44 H44 120.7 . .
C44 C45 C41 120.1(5) . .
C44 C45 H45 120.0 . .
C41 C45 H45 120.0 . .
O2 B1 O1 105.6(3) . .
O2 B1 O6 113.8(4) . .
O1 B1 O6 110.9(3) . .
O2 B1 O5 109.6(3) . .
O1 B1 O5 113.2(4) . .
O6 B1 O5 103.9(3) . .
O4 B2 O4 114.7(7) . 2_655
O4 B2 O3 105.04(17) . .
O4 B2 O3 110.0(2) 2_655 .
O4 B2 O3 110.0(2) . 2_655
O4 B2 O3 105.03(17) 2_655 2_655
O3 B2 O3 112.2(7) . 2_655
C13 N1 C12 113.7(8) . .
C27 N2 C28 113.6(6) . .
C43 N3 C42 117.8(5) . .
C2 O1 B1 106.8(3) . .
C3 O2 B1 106.7(3) . .
C17 O3 B2 106.9(3) . .
C18 O4 B2 107.1(3) . .
C32 O5 B1 108.0(3) . .
C33 O6 B1 107.9(3) . .
N1A C1A H1AA 109.5 . .
N1A C1A H1AB 109.5 . .
H1AA C1A H1AB 109.5 . .
N1A C1A H1AC 109.5 . .
H1AA C1A H1AC 109.5 . .
H1AB C1A H1AC 109.5 . .
N1A C2A H2AA 109.5 . .
N1A C2A H2AB 109.5 . .
H2AA C2A H2AB 109.5 . .
N1A C2A H2AC 109.5 . .
H2AA C2A H2AC 109.5 . .
H2AB C2A H2AC 109.5 . .
N1A C3A H3AA 109.5 . .
N1A C3A H3AB 109.5 . .
H3AA C3A H3AB 109.5 . .
N1A C3A H3AC 109.5 . .
H3AA C3A H3AC 109.5 . .
H3AB C3A H3AC 109.5 . .
N1A C4A H4AA 109.5 . .
N1A C4A H4AB 109.5 . .
H4AA C4A H4AB 109.5 . .
N1A C4A H4AC 109.5 . .
H4AA C4A H4AC 109.5 . .
H4AB C4A H4AC 109.5 . .
C2A N1A C3A 111.8(8) . .
C2A N1A C1A 108.0(8) . .
C3A N1A C1A 104.6(9) . .
C2A N1A C4A 108.2(8) . .
C3A N1A C4A 118.1(8) . .
C1A N1A C4A 105.6(7) . .
N1B C1B H1BA 109.5 . .
N1B C1B H1BB 109.5 . .
H1BA C1B H1BB 109.5 . .
N1B C1B H1BC 109.5 . .
H1BA C1B H1BC 109.5 . .
H1BB C1B H1BC 109.5 . .
N1B C2B H2BA 109.5 . .
N1B C2B H2BB 109.5 . .
H2BA C2B H2BB 109.5 . .
N1B C2B H2BC 109.5 . .
H2BA C2B H2BC 109.5 . .
H2BB C2B H2BC 109.5 . .
N1B C3B H3BA 109.5 . .
N1B C3B H3BB 109.5 . .
H3BA C3B H3BB 109.5 . .
N1B C3B H3BC 109.5 . .
H3BA C3B H3BC 109.5 . .
H3BB C3B H3BC 109.5 . .
N1B C4B H4BA 109.5 . .
N1B C4B H4BB 109.5 . .
H4BA C4B H4BB 109.5 . .
N1B C4B H4BC 109.5 . .
H4BA C4B H4BC 109.5 . .
H4BB C4B H4BC 109.5 . .
C2B N1B C1B 118(2) . .
C2B N1B C3B 104(2) . .
C1B N1B C3B 108.3(19) . .
C2B N1B C4B 101(2) . .
C1B N1B C4B 107.6(19) . .
C3B N1B C4B 119(2) . .
O1C C1C N1C 122.3(17) . .
O1C C1C H1C 118.8 . .
N1C C1C H1C 118.8 . .
N1C C2C H2CA 109.5 . .
N1C C2C H2CB 109.5 . .
H2CA C2C H2CB 109.5 . .
N1C C2C H2CC 109.5 . .
H2CA C2C H2CC 109.5 . .
H2CB C2C H2CC 109.5 . .
N1C C3C H3CA 109.5 . .
N1C C3C H3CB 109.5 . .
H3CA C3C H3CB 109.5 . .
N1C C3C H3CC 109.5 . .
H3CA C3C H3CC 109.5 . .
H3CB C3C H3CC 109.5 . .
C1C N1C C3C 117.5(13) . .
C1C N1C C2C 121.0(13) . .
C3C N1C C2C 120.7(10) . .
O1D C1D N1D 130(4) . .
O1D C1D H1D 114.8 . .
N1D C1D H1D 114.8 . .
N1D C2D H2DA 109.5 . .
N1D C2D H2DB 109.5 . .
H2DA C2D H2DB 109.5 . .
N1D C2D H2DC 109.5 . .
H2DA C2D H2DC 109.5 . .
H2DB C2D H2DC 109.5 . .
N1D C3D H3DA 109.5 . .
N1D C3D H3DB 109.5 . .
H3DA C3D H3DB 109.5 . .
N1D C3D H3DC 109.5 . .
H3DA C3D H3DC 109.5 . .
H3DB C3D H3DC 109.5 . .
C1D N1D C3D 124(3) . .
C1D N1D C2D 117(2) . .
C3D N1D C2D 118(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.376(6) .
C1 C10 1.430(6) .
C1 C16 1.499(6) .
C2 O1 1.356(5) .
C2 C3 1.394(6) .
C3 C4 1.356(6) .
C3 O2 1.364(5) .
C4 C5 1.446(6) .
C4 H4 0.9300 .
C5 C10 1.408(6) .
C5 C6 1.418(6) .
C6 C7 1.381(7) .
C6 H6 0.9300 .
C7 C8 1.383(7) .
C7 C11 1.466(7) .
C8 C9 1.386(7) .
C8 H8 0.9300 .
C9 C10 1.426(6) .
C9 H9 0.9300 .
C11 C12 1.339(10) .
C11 C15 1.408(9) .
C12 N1 1.421(10) .
C12 H12 0.9300 .
C13 C14 1.289(12) .
C13 N1 1.312(12) .
C13 H13 0.9300 .
C14 C15 1.374(10) .
C14 H14 0.9300 .
C15 H15 0.9300 .
C16 C17 1.341(6) .
C16 C25 1.439(5) .
C17 O3 1.379(5) .
C17 C18 1.395(7) .
C18 O4 1.354(6) .
C18 C19 1.365(6) .
C19 C20 1.435(7) .
C19 H19 0.9300 .
C20 C25 1.408(6) .
C20 C21 1.414(6) .
C21 C22 1.364(7) .
C21 H21 0.9300 .
C22 C23 1.405(6) .
C22 C26 1.495(6) .
C23 C24 1.371(5) .
C23 H23 0.9300 .
C24 C25 1.422(6) .
C24 H24 0.9300 .
C26 C27 1.363(8) .
C26 C30 1.372(7) .
C27 N2 1.358(7) .
C27 H27 0.9300 .
C28 C29 1.302(9) .
C28 N2 1.387(10) .
C28 H28 0.9300 .
C29 C30 1.376(7) .
C29 H29 0.9300 .
C30 H30 0.9300 .
C31 C32 1.371(5) .
C31 C40 1.423(5) .
C31 C31 1.503(6) 2_655
C32 O5 1.347(4) .
C32 C33 1.420(5) .
C33 O6 1.352(5) .
C33 C34 1.354(5) .
C34 C35 1.398(6) .
C34 H34 0.9300 .
C35 C36 1.423(6) .
C35 C40 1.447(5) .
C36 C37 1.356(6) .
C36 H36 0.9300 .
C37 C38 1.406(6) .
C37 C41 1.489(6) .
C38 C39 1.346(6) .
C38 H38 0.9300 .
C39 C40 1.410(6) .
C39 H39 0.9300 .
C41 C42 1.380(7) .
C41 C45 1.380(6) .
C42 N3 1.348(7) .
C42 H42 0.9300 .
C43 N3 1.296(8) .
C43 C44 1.360(8) .
C43 H43 0.9300 .
C44 C45 1.370(7) .
C44 H44 0.9300 .
C45 H45 0.9300 .
B1 O2 1.466(6) .
B1 O1 1.476(5) .
B1 O6 1.486(5) .
B1 O5 1.498(5) .
B2 O4 1.476(6) .
B2 O4 1.476(6) 2_655
B2 O3 1.486(6) .
B2 O3 1.486(6) 2_655
C1A N1A 1.470(10) .
C1A H1AA 0.9600 .
C1A H1AB 0.9600 .
C1A H1AC 0.9600 .
C2A N1A 1.416(10) .
C2A H2AA 0.9600 .
C2A H2AB 0.9600 .
C2A H2AC 0.9600 .
C3A N1A 1.445(10) .
C3A H3AA 0.9600 .
C3A H3AB 0.9600 .
C3A H3AC 0.9600 .
C4A N1A 1.478(9) .
C4A H4AA 0.9600 .
C4A H4AB 0.9600 .
C4A H4AC 0.9600 .
C1B N1B 1.467(19) .
C1B H1BA 0.9600 .
C1B H1BB 0.9600 .
C1B H1BC 0.9600 .
C2B N1B 1.375(19) .
C2B H2BA 0.9600 .
C2B H2BB 0.9600 .
C2B H2BC 0.9600 .
C3B N1B 1.47(2) .
C3B H3BA 0.9600 .
C3B H3BB 0.9600 .
C3B H3BC 0.9600 .
C4B N1B 1.511(19) .
C4B H4BA 0.9600 .
C4B H4BB 0.9600 .
C4B H4BC 0.9600 .
C1C O1C 1.215(19) .
C1C N1C 1.322(15) .
C1C H1C 0.9300 .
C2C N1C 1.463(16) .
C2C H2CA 0.9600 .
C2C H2CB 0.9600 .
C2C H2CC 0.9600 .
C3C N1C 1.434(16) .
C3C H3CA 0.9600 .
C3C H3CB 0.9600 .
C3C H3CC 0.9600 .
C1D O1D 1.23(3) .
C1D N1D 1.31(2) .
C1D H1D 0.9300 .
C2D N1D 1.47(2) .
C2D H2DA 0.9600 .
C2D H2DB 0.9600 .
C2D H2DC 0.9600 .
C3D N1D 1.42(2) .
C3D H3DA 0.9600 .
C3D H3DB 0.9600 .
C3D H3DC 0.9600 .
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
C10 C1 C2 O1 177.5(4) .
C16 C1 C2 O1 -4.5(6) .
C10 C1 C2 C3 -3.5(6) .
C16 C1 C2 C3 174.5(4) .
O1 C2 C3 C4 -178.2(4) .
C1 C2 C3 C4 2.7(6) .
O1 C2 C3 O2 1.8(5) .
C1 C2 C3 O2 -177.3(4) .
O2 C3 C4 C5 -179.6(4) .
C2 C3 C4 C5 0.4(6) .
C3 C4 C5 C10 -2.4(6) .
C3 C4 C5 C6 177.1(4) .
C10 C5 C6 C7 -1.7(7) .
C4 C5 C6 C7 178.8(4) .
C5 C6 C7 C8 0.9(8) .
C5 C6 C7 C11 179.6(5) .
C6 C7 C8 C9 0.0(8) .
C11 C7 C8 C9 -178.7(5) .
C7 C8 C9 C10 -0.3(8) .
C6 C5 C10 C9 1.4(6) .
C4 C5 C10 C9 -179.1(4) .
C6 C5 C10 C1 -178.0(4) .
C4 C5 C10 C1 1.5(6) .
C8 C9 C10 C5 -0.4(7) .
C8 C9 C10 C1 178.9(4) .
C2 C1 C10 C5 1.4(6) .
C16 C1 C10 C5 -176.7(4) .
C2 C1 C10 C9 -178.0(4) .
C16 C1 C10 C9 4.0(6) .
C6 C7 C11 C12 43.2(8) .
C8 C7 C11 C12 -138.2(7) .
C6 C7 C11 C15 -141.0(6) .
C8 C7 C11 C15 37.6(8) .
C15 C11 C12 N1 3.6(11) .
C7 C11 C12 N1 179.6(6) .
N1 C13 C14 C15 6.0(16) .
C13 C14 C15 C11 -0.9(12) .
C12 C11 C15 C14 -3.4(10) .
C7 C11 C15 C14 -179.4(6) .
C2 C1 C16 C17 82.3(5) .
C10 C1 C16 C17 -99.8(5) .
C2 C1 C16 C25 -101.3(5) .
C10 C1 C16 C25 76.6(5) .
C25 C16 C17 O3 179.6(4) .
C1 C16 C17 O3 -3.8(7) .
C25 C16 C17 C18 -2.4(6) .
C1 C16 C17 C18 174.2(4) .
C16 C17 C18 O4 -177.5(4) .
O3 C17 C18 O4 0.8(5) .
C16 C17 C18 C19 4.1(7) .
O3 C17 C18 C19 -177.6(4) .
O4 C18 C19 C20 178.6(4) .
C17 C18 C19 C20 -3.2(7) .
C18 C19 C20 C25 1.2(6) .
C18 C19 C20 C21 -178.6(4) .
C25 C20 C21 C22 -2.2(7) .
C19 C20 C21 C22 177.6(4) .
C20 C21 C22 C23 2.7(7) .
C20 C21 C22 C26 -178.8(4) .
C21 C22 C23 C24 -2.0(7) .
C26 C22 C23 C24 179.4(4) .
C22 C23 C24 C25 0.9(7) .
C21 C20 C25 C24 1.0(6) .
C19 C20 C25 C24 -178.8(4) .
C21 C20 C25 C16 -179.9(4) .
C19 C20 C25 C16 0.3(6) .
C23 C24 C25 C20 -0.4(6) .
C23 C24 C25 C16 -179.5(4) .
C17 C16 C25 C20 0.2(6) .
C1 C16 C25 C20 -176.4(4) .
C17 C16 C25 C24 179.3(4) .
C1 C16 C25 C24 2.7(6) .
C21 C22 C26 C27 140.0(6) .
C23 C22 C26 C27 -41.5(8) .
C21 C22 C26 C30 -40.5(7) .
C23 C22 C26 C30 138.0(5) .
C30 C26 C27 N2 4.6(11) .
C22 C26 C27 N2 -175.8(7) .
N2 C28 C29 C30 3.3(13) .
C27 C26 C30 C29 -3.2(9) .
C22 C26 C30 C29 177.3(5) .
C28 C29 C30 C26 -0.5(10) .
C40 C31 C32 O5 -179.4(4) .
C31 C31 C32 O5 -4.7(7) 2_655
C40 C31 C32 C33 -1.5(6) .
C31 C31 C32 C33 173.2(4) 2_655
O5 C32 C33 O6 1.9(5) .
C31 C32 C33 O6 -176.4(3) .
O5 C32 C33 C34 -179.8(4) .
C31 C32 C33 C34 1.9(6) .
O6 C33 C34 C35 177.6(4) .
C32 C33 C34 C35 -0.3(6) .
C33 C34 C35 C36 -178.7(4) .
C33 C34 C35 C40 -1.5(6) .
C34 C35 C36 C37 176.8(4) .
C40 C35 C36 C37 -0.4(7) .
C35 C36 C37 C38 0.9(7) .
C35 C36 C37 C41 -178.2(4) .
C36 C37 C38 C39 -0.2(8) .
C41 C37 C38 C39 179.0(5) .
C37 C38 C39 C40 -1.1(8) .
C38 C39 C40 C31 -178.4(4) .
C38 C39 C40 C35 1.5(7) .
C32 C31 C40 C39 179.6(4) .
C31 C31 C40 C39 4.8(6) 2_655
C32 C31 C40 C35 -0.3(6) .
C31 C31 C40 C35 -175.1(4) 2_655
C34 C35 C40 C39 -178.1(4) .
C36 C35 C40 C39 -0.7(6) .
C34 C35 C40 C31 1.8(6) .
C36 C35 C40 C31 179.2(4) .
C36 C37 C41 C42 133.0(7) .
C38 C37 C41 C42 -46.1(8) .
C36 C37 C41 C45 -43.8(8) .
C38 C37 C41 C45 137.0(6) .
C45 C41 C42 N3 -1.5(12) .
C37 C41 C42 N3 -178.5(8) .
N3 C43 C44 C45 4.4(13) .
C43 C44 C45 C41 -3.0(10) .
C42 C41 C45 C44 1.6(9) .
C37 C41 C45 C44 178.6(5) .
C14 C13 N1 C12 -5.6(16) .
C11 C12 N1 C13 0.4(13) .
C26 C27 N2 C28 -2.2(13) .
C29 C28 N2 C27 -2.0(13) .
C44 C43 N3 C42 -4.2(14) .
C41 C42 N3 C43 2.8(14) .
C1 C2 O1 B1 178.8(4) .
C3 C2 O1 B1 -0.2(4) .
O2 B1 O1 C2 -1.3(4) .
O6 B1 O1 C2 -125.0(4) .
O5 B1 O1 C2 118.7(4) .
C4 C3 O2 B1 177.4(4) .
C2 C3 O2 B1 -2.5(4) .
O1 B1 O2 C3 2.3(4) .
O6 B1 O2 C3 124.2(3) .
O5 B1 O2 C3 -119.9(3) .
C16 C17 O3 B2 177.0(5) .
C18 C17 O3 B2 -1.3(5) .
O4 B2 O3 C17 1.2(5) .
O4 B2 O3 C17 -122.7(4) 2_655
O3 B2 O3 C17 120.8(3) 2_655
C19 C18 O4 B2 178.4(5) .
C17 C18 O4 B2 0.1(6) .
O4 B2 O4 C18 120.1(4) 2_655
O3 B2 O4 C18 -0.8(5) .
O3 B2 O4 C18 -121.8(4) 2_655
C31 C32 O5 B1 176.4(4) .
C33 C32 O5 B1 -1.7(4) .
O2 B1 O5 C32 -121.1(3) .
O1 B1 O5 C32 121.3(4) .
O6 B1 O5 C32 0.9(4) .
C34 C33 O6 B1 -179.4(4) .
C32 C33 O6 B1 -1.2(4) .
O2 B1 O6 C33 119.4(4) .
O1 B1 O6 C33 -121.6(4) .
O5 B1 O6 C33 0.2(4) .
O1C C1C N1C C3C 174.9(16) .
O1C C1C N1C C2C 5(2) .
O1D C1D N1D C3D -177.7(15) .
O1D C1D N1D C2D -2(2) .
