#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/26/2222689.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222689
loop_
_publ_author_name
'Alhassan, Abdul-Basit'
'Norris, Peter'
'Zeller, Matthias'
_publ_section_title
4-Butyl-1-(2,3,4-tri-O-acetyl-β-<small>L</small>-fucopyranosyl)-1H-1,2,3-triazole
_journal_coeditor_code           FL2257
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1992
_journal_page_last               o1993
_journal_paper_doi               10.1107/S1600536809028700
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H27 N3 O7'
_chemical_formula_moiety         'C18 H27 N3 O7'
_chemical_formula_sum            'C18 H27 N3 O7'
_chemical_formula_weight         397.43
_chemical_name_systematic
4-Butyl-1-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-1H-1,2,3-triazole
_space_group_IT_number           1
_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                94.5070(10)
_cell_angle_beta                 96.1510(10)
_cell_angle_gamma                91.2270(10)
_cell_formula_units_Z            2
_cell_length_a                   5.5173(3)
_cell_length_b                   7.7442(4)
_cell_length_c                   24.1013(13)
_cell_measurement_reflns_used    9354
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      2.56
_cell_volume                     1020.22(9)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008); publCIF (Westrip, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution
;
SHELXTL (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ω
_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  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            10512
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         0.85
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS in SAINT-Plus; Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.212
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     515
_refine_ls_number_reflns         5041
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0456
_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)+(0.0771P)²+0.17P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1197
_reflns_number_gt                4839
_reflns_number_total             5041
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2257.cif
_cod_data_source_block           I
_cod_database_code               2222689
_cod_database_fobs_code          2222689
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1A 0.1284(4) 0.5904(3) 0.25737(10) 0.0160(4) Uani d . 1 . .
H H1A 0.2899 0.5447 0.2490 0.019 Uiso calc R 1 . .
C C2A 0.0093(4) 0.4715(3) 0.29447(10) 0.0160(4) Uani d . 1 . .
H H2A -0.1530 0.5159 0.3027 0.019 Uiso calc R 1 . .
C C3A 0.1762(4) 0.4617(3) 0.34855(10) 0.0172(4) Uani d . 1 . .
H H3A 0.3249 0.3967 0.3405 0.021 Uiso calc R 1 . .
C C4A 0.2522(4) 0.6418(3) 0.37653(10) 0.0178(5) Uani d . 1 . .
H H4A 0.3898 0.6301 0.4064 0.021 Uiso calc R 1 . .
C C5A 0.3353(5) 0.7604(3) 0.33445(11) 0.0201(5) Uani d . 1 . .
H H5A 0.4950 0.7206 0.3229 0.024 Uiso calc R 1 . .
C C6A 0.3639(6) 0.9487(4) 0.35723(13) 0.0282(6) Uani d . 1 . .
H H6A1 0.4299 1.0173 0.3295 0.042 Uiso calc R 1 . .
H H6A2 0.4757 0.9583 0.3919 0.042 Uiso calc R 1 . .
H H6A3 0.2045 0.9923 0.3650 0.042 Uiso calc R 1 . .
C C7A 0.0505(5) 0.6379(3) 0.15536(11) 0.0186(5) Uani d . 1 . .
H H7A 0.2127 0.6396 0.1455 0.022 Uiso calc R 1 . .
C C8A -0.1595(4) 0.6638(3) 0.12178(11) 0.0189(5) Uani d . 1 . .
C C9A -0.1947(5) 0.7003(4) 0.06140(12) 0.0238(5) Uani d . 1 . .
H H9A1 -0.2156 0.8262 0.0590 0.029 Uiso calc R 1 . .
H H9A2 -0.3463 0.6399 0.0434 0.029 Uiso calc R 1 . .
C C10A 0.0155(5) 0.6439(4) 0.02915(11) 0.0226(5) Uani d . 1 . .
H H10A 0.0396 0.5186 0.0323 0.027 Uiso calc R 1 . .
H H10B 0.1665 0.7070 0.0463 0.027 Uiso calc R 1 . .
C C11A -0.0269(5) 0.6775(5) -0.03262(12) 0.0307(6) Uani d . 1 . .
H H11A -0.1812 0.6180 -0.0494 0.037 Uiso calc R 1 . .
H H11B -0.0451 0.8034 -0.0357 0.037 Uiso calc R 1 . .
C C12A 0.1782(6) 0.6156(5) -0.06548(13) 0.0351(7) Uani d . 1 . .
H H12A 0.3314 0.6749 -0.0494 0.053 Uiso calc R 1 . .
H H12B 0.1425 0.6416 -0.1046 0.053 Uiso calc R 1 . .
H H12C 0.1936 0.4903 -0.0637 0.053 Uiso calc R 1 . .
C C13A -0.2440(4) 0.2243(3) 0.26034(11) 0.0192(5) Uani d . 1 . .
C C14A -0.2384(5) 0.0438(3) 0.23312(12) 0.0248(5) Uani d . 1 . .
H H14A -0.1490 -0.0299 0.2590 0.037 Uiso calc R 1 . .
H H14B -0.1569 0.0458 0.1990 0.037 Uiso calc R 1 . .
H H14C -0.4056 -0.0026 0.2235 0.037 Uiso calc R 1 . .
C C15A 0.1526(5) 0.3080(3) 0.43018(12) 0.0234(5) Uani d . 1 . .
C C16A -0.0247(6) 0.2183(5) 0.46177(14) 0.0367(7) Uani d . 1 . .
H H16A 0.0645 0.1544 0.4906 0.055 Uiso calc R 1 . .
H H16B -0.1292 0.1373 0.4359 0.055 Uiso calc R 1 . .
H H16C -0.1257 0.3043 0.4795 0.055 Uiso calc R 1 . .
C C17A 0.0802(5) 0.7476(3) 0.45847(11) 0.0207(5) Uani d . 1 . .
C C18A -0.1564(5) 0.7616(4) 0.48340(13) 0.0286(6) Uani d . 1 . .
H H18A -0.1241 0.7955 0.5236 0.043 Uiso calc R 1 . .
H H18B -0.2447 0.6494 0.4777 0.043 Uiso calc R 1 . .
H H18C -0.2553 0.8492 0.4653 0.043 Uiso calc R 1 . .
N N1A -0.0240(4) 0.6093(3) 0.20568(9) 0.0166(4) Uani d . 1 . .
N N2A -0.2688(4) 0.6186(3) 0.20427(10) 0.0204(4) Uani d . 1 . .
N N3A -0.3509(4) 0.6499(3) 0.15312(10) 0.0203(4) Uani d . 1 . .
O O1A 0.1606(3) 0.7576(2) 0.28548(8) 0.0195(4) Uani d . 1 . .
O O2A -0.0188(3) 0.3011(2) 0.26588(8) 0.0181(3) Uani d . 1 . .
O O3A -0.4211(3) 0.2926(3) 0.27577(9) 0.0262(4) Uani d . 1 . .
O O4A 0.0358(3) 0.3647(2) 0.38316(8) 0.0216(4) Uani d . 1 . .
O O5A 0.3664(4) 0.3301(3) 0.44336(9) 0.0329(5) Uani d . 1 . .
O O6A 0.0444(3) 0.7086(2) 0.40218(8) 0.0205(4) Uani d . 1 . .
O O7A 0.2785(4) 0.7661(4) 0.48414(9) 0.0385(6) Uani d . 1 . .
C C1B 0.2703(4) 0.9784(3) 0.80834(10) 0.0174(5) Uani d . 1 . .
H H1B 0.1076 0.9344 0.8168 0.021 Uiso calc R 1 . .
C C2B 0.3807(4) 0.8444(3) 0.76952(11) 0.0166(4) Uani d . 1 . .
H H2B 0.5439 0.8862 0.7608 0.020 Uiso calc R 1 . .
C C3B 0.2060(4) 0.8121(3) 0.71631(10) 0.0186(5) Uani d . 1 . .
H H3B 0.0553 0.7500 0.7248 0.022 Uiso calc R 1 . .
C C4B 0.1364(4) 0.9804(3) 0.69039(11) 0.0193(5) Uani d . 1 . .
H H4B -0.0028 0.9557 0.6605 0.023 Uiso calc R 1 . .
C C5B 0.0619(5) 1.1164(4) 0.73393(11) 0.0212(5) Uani d . 1 . .
H H5B -0.0975 1.0789 0.7460 0.025 Uiso calc R 1 . .
C C6B 0.0375(6) 1.2960(4) 0.71358(12) 0.0275(6) Uani d . 1 . .
H H6B1 -0.0147 1.3756 0.7434 0.041 Uiso calc R 1 . .
H H6B2 -0.0838 1.2920 0.6806 0.041 Uiso calc R 1 . .
H H6B3 0.1953 1.3367 0.7036 0.041 Uiso calc R 1 . .
C C7B 0.3525(5) 1.0728(3) 0.91047(11) 0.0195(5) Uani d . 1 . .
H H7B 0.1904 1.0772 0.9203 0.023 Uiso calc R 1 . .
C C8B 0.5642(4) 1.1177(3) 0.94397(11) 0.0187(5) Uani d . 1 . .
C C9B 0.6021(5) 1.1841(4) 1.00422(12) 0.0244(5) Uani d . 1 . .
H H9B1 0.6318 1.3111 1.0067 0.029 Uiso calc R 1 . .
H H9B2 0.7496 1.1320 1.0222 0.029 Uiso calc R 1 . .
C C10B 0.3876(5) 1.1448(4) 1.03638(11) 0.0232(5) Uani d . 1 . .
H H10C 0.2409 1.1995 1.0190 0.028 Uiso calc R 1 . .
H H10D 0.3552 1.0180 1.0332 0.028 Uiso calc R 1 . .
C C11B 0.4303(6) 1.2089(5) 1.09785(12) 0.0309(6) Uani d . 1 . .
H H11C 0.4583 1.3361 1.1010 0.037 Uiso calc R 1 . .
H H11D 0.5800 1.1568 1.1149 0.037 Uiso calc R 1 . .
C C12B 0.2200(6) 1.1658(5) 1.13071(13) 0.0351(7) Uani d . 1 . .
H H12D 0.0720 1.2198 1.1149 0.053 Uiso calc R 1 . .
H H12E 0.2593 1.2100 1.1699 0.053 Uiso calc R 1 . .
H H12F 0.1931 1.0399 1.1285 0.053 Uiso calc R 1 . .
C C13B 0.6276(5) 0.6187(3) 0.80445(11) 0.0192(5) Uani d . 1 . .
C C14B 0.6181(5) 0.4532(4) 0.83252(13) 0.0264(6) Uani d . 1 . .
H H14D 0.5291 0.3635 0.8068 0.040 Uiso calc R 1 . .
H H14E 0.5345 0.4719 0.8663 0.040 Uiso calc R 1 . .
H H14F 0.7844 0.4160 0.8428 0.040 Uiso calc R 1 . .
C C15B 0.1945(6) 0.6211(4) 0.63345(12) 0.0272(6) Uani d . 1 . .
C C16B 0.3516(7) 0.5229(5) 0.59592(14) 0.0402(8) Uani d . 1 . .
H H16D 0.2618 0.4193 0.5779 0.060 Uiso calc R 1 . .
H H16E 0.4996 0.4886 0.6181 0.060 Uiso calc R 1 . .
H H16F 0.3965 0.5967 0.5672 0.060 Uiso calc R 1 . .
C C17B 0.3086(5) 1.0620(4) 0.60971(11) 0.0218(5) Uani d . 1 . .
C C18B 0.5441(5) 1.0822(5) 0.58499(13) 0.0306(6) Uani d . 1 . .
H H18D 0.5115 1.1205 0.5472 0.046 Uiso calc R 1 . .
H H18E 0.6251 0.9709 0.5832 0.046 Uiso calc R 1 . .
H H18F 0.6498 1.1686 0.6084 0.046 Uiso calc R 1 . .
N N1B 0.4259(4) 1.0209(3) 0.86032(9) 0.0166(4) Uani d . 1 . .
N N2B 0.6712(4) 1.0341(3) 0.86152(10) 0.0202(4) Uani d . 1 . .
N N3B 0.7542(4) 1.0919(3) 0.91256(9) 0.0201(4) Uani d . 1 . .
O O1B 0.2423(3) 1.1344(2) 0.78221(8) 0.0195(4) Uani d . 1 . .
O O2B 0.4016(3) 0.6857(2) 0.79666(8) 0.0187(3) Uani d . 1 . .
O O3B 0.8064(3) 0.6837(3) 0.78989(10) 0.0285(4) Uani d . 1 . .
O O4B 0.3322(4) 0.7019(2) 0.67849(8) 0.0228(4) Uani d . 1 . .
O O5B -0.0221(4) 0.6326(3) 0.62559(10) 0.0363(5) Uani d . 1 . .
O O6B 0.3468(3) 1.0408(2) 0.66523(8) 0.0209(4) Uani d . 1 . .
O O7B 0.1098(4) 1.0641(4) 0.58456(9) 0.0352(5) Uani d . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1A C1A N1A . . 106.41(19) ?
O1A C1A C2A . . 108.84(19) ?
N1A C1A C2A . . 111.89(19) ?
O1A C1A H1A . . 109.9 ?
N1A C1A H1A . . 109.9 ?
C2A C1A H1A . . 109.9 ?
O2A C2A C1A . . 108.36(19) ?
O2A C2A C3A . . 108.51(19) ?
C1A C2A C3A . . 108.96(19) ?
O2A C2A H2A . . 110.3 ?
C1A C2A H2A . . 110.3 ?
C3A C2A H2A . . 110.3 ?
O4A C3A C2A . . 104.62(19) ?
O4A C3A C4A . . 111.7(2) ?
C2A C3A C4A . . 111.91(19) ?
O4A C3A H3A . . 109.5 ?
C2A C3A H3A . . 109.5 ?
C4A C3A H3A . . 109.5 ?
O6A C4A C5A . . 111.8(2) ?
O6A C4A C3A . . 107.00(19) ?
C5A C4A C3A . . 111.2(2) ?
O6A C4A H4A . . 108.9 ?
C5A C4A H4A . . 108.9 ?
C3A C4A H4A . . 108.9 ?
O1A C5A C6A . . 105.6(2) ?
O1A C5A C4A . . 111.2(2) ?
C6A C5A C4A . . 113.1(2) ?
O1A C5A H5A . . 108.9 ?
C6A C5A H5A . . 108.9 ?
C4A C5A H5A . . 108.9 ?
C5A C6A H6A1 . . 109.5 ?
C5A C6A H6A2 . . 109.5 ?
H6A1 C6A H6A2 . . 109.5 ?
C5A C6A H6A3 . . 109.5 ?
H6A1 C6A H6A3 . . 109.5 ?
H6A2 C6A H6A3 . . 109.5 ?
N1A C7A C8A . . 104.7(2) ?
N1A C7A H7A . . 127.6 ?
C8A C7A H7A . . 127.6 ?
C7A C8A N3A . . 107.9(2) ?
C7A C8A C9A . . 129.8(2) ?
N3A C8A C9A . . 122.3(2) ?
C8A C9A C10A . . 113.5(2) ?
C8A C9A H9A1 . . 108.9 ?
C10A C9A H9A1 . . 108.9 ?
C8A C9A H9A2 . . 108.9 ?
C10A C9A H9A2 . . 108.9 ?
H9A1 C9A H9A2 . . 107.7 ?
C9A C10A C11A . . 112.7(2) ?
C9A C10A H10A . . 109.0 ?
C11A C10A H10A . . 109.0 ?
C9A C10A H10B . . 109.0 ?
C11A C10A H10B . . 109.0 ?
H10A C10A H10B . . 107.8 ?
C12A C11A C10A . . 113.0(2) ?
C12A C11A H11A . . 109.0 ?
C10A C11A H11A . . 109.0 ?
C12A C11A H11B . . 109.0 ?
C10A C11A H11B . . 109.0 ?
H11A C11A H11B . . 107.8 ?
C11A C12A H12A . . 109.5 ?
C11A C12A H12B . . 109.5 ?
H12A C12A H12B . . 109.5 ?
C11A C12A H12C . . 109.5 ?
H12A C12A H12C . . 109.5 ?
H12B C12A H12C . . 109.5 ?
O3A C13A O2A . . 124.0(2) ?
O3A C13A C14A . . 125.5(2) ?
O2A C13A C14A . . 110.5(2) ?
C13A C14A H14A . . 109.5 ?
C13A C14A H14B . . 109.5 ?
H14A C14A H14B . . 109.5 ?
C13A C14A H14C . . 109.5 ?
H14A C14A H14C . . 109.5 ?
H14B C14A H14C . . 109.5 ?
O5A C15A O4A . . 123.3(3) ?
O5A C15A C16A . . 126.7(3) ?
O4A C15A C16A . . 110.0(2) ?
C15A C16A H16A . . 109.5 ?
C15A C16A H16B . . 109.5 ?
H16A C16A H16B . . 109.5 ?
C15A C16A H16C . . 109.5 ?
H16A C16A H16C . . 109.5 ?
H16B C16A H16C . . 109.5 ?
O7A C17A O6A . . 123.1(2) ?
O7A C17A C18A . . 125.3(3) ?
O6A C17A C18A . . 111.6(2) ?
C17A C18A H18A . . 109.5 ?
C17A C18A H18B . . 109.5 ?
H18A C18A H18B . . 109.5 ?
C17A C18A H18C . . 109.5 ?
H18A C18A H18C . . 109.5 ?
H18B C18A H18C . . 109.5 ?
N2A N1A C7A . . 111.1(2) ?
N2A N1A C1A . . 121.4(2) ?
C7A N1A C1A . . 127.1(2) ?
N3A N2A N1A . . 106.6(2) ?
N2A N3A C8A . . 109.6(2) ?
C1A O1A C5A . . 111.88(18) ?
C13A O2A C2A . . 117.27(19) ?
C15A O4A C3A . . 117.9(2) ?
C17A O6A C4A . . 115.87(19) ?
O1B C1B N1B . . 106.14(19) ?
O1B C1B C2B . . 109.43(19) ?
N1B C1B C2B . . 112.5(2) ?
O1B C1B H1B . . 109.6 ?
N1B C1B H1B . . 109.6 ?
C2B C1B H1B . . 109.6 ?
O2B C2B C3B . . 108.53(19) ?
O2B C2B C1B . . 108.20(19) ?
C3B C2B C1B . . 108.09(19) ?
O2B C2B H2B . . 110.6 ?
C3B C2B H2B . . 110.6 ?
C1B C2B H2B . . 110.6 ?
O4B C3B C2B . . 105.76(19) ?
O4B C3B C4B . . 110.6(2) ?
C2B C3B C4B . . 112.0(2) ?
O4B C3B H3B . . 109.5 ?
C2B C3B H3B . . 109.5 ?
C4B C3B H3B . . 109.5 ?
O6B C4B C5B . . 110.9(2) ?
O6B C4B C3B . . 107.1(2) ?
C5B C4B C3B . . 111.6(2) ?
O6B C4B H4B . . 109.1 ?
C5B C4B H4B . . 109.1 ?
C3B C4B H4B . . 109.1 ?
O1B C5B C6B . . 105.7(2) ?
O1B C5B C4B . . 110.5(2) ?
C6B C5B C4B . . 114.1(2) ?
O1B C5B H5B . . 108.8 ?
C6B C5B H5B . . 108.8 ?
C4B C5B H5B . . 108.8 ?
C5B C6B H6B1 . . 109.5 ?
C5B C6B H6B2 . . 109.5 ?
H6B1 C6B H6B2 . . 109.5 ?
C5B C6B H6B3 . . 109.5 ?
H6B1 C6B H6B3 . . 109.5 ?
H6B2 C6B H6B3 . . 109.5 ?
N1B C7B C8B . . 104.4(2) ?
N1B C7B H7B . . 127.8 ?
C8B C7B H7B . . 127.8 ?
N3B C8B C7B . . 108.0(2) ?
N3B C8B C9B . . 122.2(2) ?
C7B C8B C9B . . 129.8(2) ?
C8B C9B C10B . . 113.5(2) ?
C8B C9B H9B1 . . 108.9 ?
C10B C9B H9B1 . . 108.9 ?
C8B C9B H9B2 . . 108.9 ?
C10B C9B H9B2 . . 108.9 ?
H9B1 C9B H9B2 . . 107.7 ?
C11B C10B C9B . . 113.1(2) ?
C11B C10B H10C . . 108.9 ?
C9B C10B H10C . . 108.9 ?
C11B C10B H10D . . 108.9 ?
C9B C10B H10D . . 108.9 ?
H10C C10B H10D . . 107.8 ?
C10B C11B C12B . . 113.6(3) ?
C10B C11B H11C . . 108.9 ?
C12B C11B H11C . . 108.9 ?
C10B C11B H11D . . 108.9 ?
C12B C11B H11D . . 108.9 ?
H11C C11B H11D . . 107.7 ?
C11B C12B H12D . . 109.5 ?
C11B C12B H12E . . 109.5 ?
H12D C12B H12E . . 109.5 ?
C11B C12B H12F . . 109.5 ?
H12D C12B H12F . . 109.5 ?
H12E C12B H12F . . 109.5 ?
O3B C13B O2B . . 123.8(2) ?
O3B C13B C14B . . 125.6(2) ?
O2B C13B C14B . . 110.6(2) ?
C13B C14B H14D . . 109.5 ?
C13B C14B H14E . . 109.5 ?
H14D C14B H14E . . 109.5 ?
C13B C14B H14F . . 109.5 ?
H14D C14B H14F . . 109.5 ?
H14E C14B H14F . . 109.5 ?
O5B C15B O4B . . 123.1(3) ?
O5B C15B C16B . . 126.2(3) ?
O4B C15B C16B . . 110.7(3) ?
C15B C16B H16D . . 109.5 ?
C15B C16B H16E . . 109.5 ?
H16D C16B H16E . . 109.5 ?
C15B C16B H16F . . 109.5 ?
H16D C16B H16F . . 109.5 ?
H16E C16B H16F . . 109.5 ?
O7B C17B O6B . . 123.2(2) ?
O7B C17B C18B . . 125.3(3) ?
O6B C17B C18B . . 111.5(2) ?
C17B C18B H18D . . 109.5 ?
C17B C18B H18E . . 109.5 ?
H18D C18B H18E . . 109.5 ?
C17B C18B H18F . . 109.5 ?
H18D C18B H18F . . 109.5 ?
H18E C18B H18F . . 109.5 ?
C7B N1B N2B . . 111.4(2) ?
C7B N1B C1B . . 126.5(2) ?
N2B N1B C1B . . 121.5(2) ?
N3B N2B N1B . . 106.3(2) ?
N2B N3B C8B . . 109.8(2) ?
C1B O1B C5B . . 111.96(19) ?
C13B O2B C2B . . 117.18(19) ?
C15B O4B C3B . . 116.7(2) ?
C17B O6B C4B . . 115.64(19) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1A O1A . 1.412(3) ?
C1A N1A . 1.446(3) ?
C1A C2A . 1.519(3) ?
C1A H1A . 1.0000 ?
C2A O2A . 1.437(3) ?
C2A C3A . 1.521(3) ?
C2A H2A . 1.0000 ?
C3A O4A . 1.440(3) ?
C3A C4A . 1.530(3) ?
C3A H3A . 1.0000 ?
C4A O6A . 1.446(3) ?
C4A C5A . 1.520(4) ?
C4A H4A . 1.0000 ?
C5A O1A . 1.440(3) ?
C5A C6A . 1.516(4) ?
C5A H5A . 1.0000 ?
C6A H6A1 . 0.9800 ?
C6A H6A2 . 0.9800 ?
C6A H6A3 . 0.9800 ?
C7A N1A . 1.354(3) ?
C7A C8A . 1.369(3) ?
C7A H7A . 0.9500 ?
C8A N3A . 1.369(3) ?
C8A C9A . 1.497(4) ?
C9A C10A . 1.517(4) ?
C9A H9A1 . 0.9900 ?
C9A H9A2 . 0.9900 ?
C10A C11A . 1.526(4) ?
C10A H10A . 0.9900 ?
C10A H10B . 0.9900 ?
C11A C12A . 1.514(4) ?
C11A H11A . 0.9900 ?
C11A H11B . 0.9900 ?
C12A H12A . 0.9800 ?
C12A H12B . 0.9800 ?
C12A H12C . 0.9800 ?
C13A O3A . 1.200(3) ?
C13A O2A . 1.355(3) ?
C13A C14A . 1.500(4) ?
C14A H14A . 0.9800 ?
C14A H14B . 0.9800 ?
C14A H14C . 0.9800 ?
C15A O5A . 1.193(4) ?
C15A O4A . 1.351(3) ?
C15A C16A . 1.495(4) ?
C16A H16A . 0.9800 ?
C16A H16B . 0.9800 ?
C16A H16C . 0.9800 ?
C17A O7A . 1.198(3) ?
C17A O6A . 1.359(3) ?
C17A C18A . 1.497(4) ?
C18A H18A . 0.9800 ?
C18A H18B . 0.9800 ?
C18A H18C . 0.9800 ?
N1A N2A . 1.351(3) ?
N2A N3A . 1.310(3) ?
C1B O1B . 1.409(3) ?
C1B N1B . 1.452(3) ?
C1B C2B . 1.523(3) ?
C1B H1B . 1.0000 ?
C2B O2B . 1.438(3) ?
C2B C3B . 1.520(3) ?
C2B H2B . 1.0000 ?
C3B O4B . 1.443(3) ?
C3B C4B . 1.528(3) ?
C3B H3B . 1.0000 ?
C4B O6B . 1.451(3) ?
C4B C5B . 1.522(4) ?
C4B H4B . 1.0000 ?
C5B O1B . 1.444(3) ?
C5B C6B . 1.515(4) ?
C5B H5B . 1.0000 ?
C6B H6B1 . 0.9800 ?
C6B H6B2 . 0.9800 ?
C6B H6B3 . 0.9800 ?
C7B N1B . 1.350(3) ?
C7B C8B . 1.369(3) ?
C7B H7B . 0.9500 ?
C8B N3B . 1.367(3) ?
C8B C9B . 1.493(4) ?
C9B C10B . 1.520(4) ?
C9B H9B1 . 0.9900 ?
C9B H9B2 . 0.9900 ?
C10B C11B . 1.517(4) ?
C10B H10C . 0.9900 ?
C10B H10D . 0.9900 ?
C11B C12B . 1.519(4) ?
C11B H11C . 0.9900 ?
C11B H11D . 0.9900 ?
C12B H12D . 0.9800 ?
C12B H12E . 0.9800 ?
C12B H12F . 0.9800 ?
C13B O3B . 1.196(3) ?
C13B O2B . 1.361(3) ?
C13B C14B . 1.498(4) ?
C14B H14D . 0.9800 ?
C14B H14E . 0.9800 ?
C14B H14F . 0.9800 ?
C15B O5B . 1.196(4) ?
C15B O4B . 1.358(3) ?
C15B C16B . 1.495(5) ?
C16B H16D . 0.9800 ?
C16B H16E . 0.9800 ?
C16B H16F . 0.9800 ?
C17B O7B . 1.196(3) ?
C17B O6B . 1.355(3) ?
C17B C18B . 1.496(4) ?
C18B H18D . 0.9800 ?
C18B H18E . 0.9800 ?
C18B H18F . 0.9800 ?
N1B N2B . 1.352(3) ?
N2B N3B . 1.307(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C1B H1B O3B 1_455 1.00 2.53 3.362(3) 141
C2A H2A O3A . 1.00 2.26 2.701(3) 105
C2B H2B O3B . 1.00 2.26 2.698(3) 105
C3A H3A O3A 1_655 1.00 2.32 3.214(3) 149
C3B H3B O3B 1_455 1.00 2.27 3.165(3) 148
C4A H4A O5A . 1.00 2.56 3.046(3) 110
C4A H4A O7A . 1.00 2.23 2.682(3) 106
C4B H4B O5B . 1.00 2.57 3.067(3) 110
C4B H4B O7B . 1.00 2.21 2.670(3) 106
C7A H7A N3A 1_655 0.95 2.39 3.308(4) 161
C7B H7B N3B 1_455 0.95 2.40 3.313(4) 161
C14A H14A O1A 1_545 0.98 2.47 3.377(3) 154
C14B H14D O1B 1_545 0.98 2.35 3.261(3) 155
C16A H16A O7B 1_545 0.98 2.41 3.295(4) 150
C16B H16F O7A . 0.98 2.51 3.401(4) 150
