#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/05/7150578.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_7150578
loop_
_publ_author_name
'Klein, Johannes E. M. N.'
'Müller-Bunz, Helge'
'Evans, Paul'
_publ_section_title
;
 Studies concerning the electrophilic amino-alkene cyclisation for the
 synthesis of bicyclic amines
;
_journal_issue                   5
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              986
_journal_page_last               995
_journal_paper_doi               10.1039/b819610a
_journal_volume                  7
_journal_year                    2009
_chemical_formula_moiety         'C9 H14 O2'
_chemical_formula_sum            'C9 H14 O2'
_chemical_formula_weight         154.20
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.092(2)
_cell_angle_beta                 93.820(2)
_cell_angle_gamma                100.303(2)
_cell_formula_units_Z            6
_cell_length_a                   7.3608(7)
_cell_length_b                   12.1760(11)
_cell_length_c                   15.1409(14)
_cell_measurement_reflns_used    4395
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     1292.3(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19207
_diffrn_reflns_theta_full        24.17
_diffrn_reflns_theta_max         24.17
_diffrn_reflns_theta_min         1.39
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9975
_exptl_absorpt_correction_T_min  0.8929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) for selected reflections was 0.130 before and 0.029 after
correction. The Ratio of minimum to maximum transmission is 0.895089.
The λ/2 correction factor is 0.0015
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4122
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0354P)²+0.3387P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0850
_reflns_number_gt                3522
_reflns_number_total             4122
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b819610a.txt
_cod_data_source_block           eva40
_cod_database_code               7150578
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.41074(12) -0.00126(8) 0.89724(6) 0.0223(2) Uani 1 1 d . . .
O2 O 1.29024(14) 0.05471(8) 1.02761(6) 0.0246(2) Uani 1 1 d . . .
H1O2 H 1.400(3) 0.0375(16) 1.0515(13) 0.061(6) Uiso 1 1 d . . .
C1 C 1.28615(19) 0.03351(11) 0.93757(9) 0.0196(3) Uani 1 1 d . . .
C2 C 1.11518(18) 0.05550(12) 0.89161(9) 0.0208(3) Uani 1 1 d . . .
H2A H 1.0954 0.1326 0.9224 0.025 Uiso 1 1 calc R . .
H2B H 1.0069 -0.0019 0.8985 0.025 Uiso 1 1 calc R . .
C3 C 1.12487(19) 0.04962(13) 0.79085(9) 0.0241(3) Uani 1 1 d . . .
H3A H 1.2250 0.1129 0.7852 0.029 Uiso 1 1 calc R . .
H3B H 1.1612 -0.0237 0.7624 0.029 Uiso 1 1 calc R . .
C4 C 0.95015(18) 0.05732(11) 0.73709(9) 0.0203(3) Uani 1 1 d . A .
C5 C 0.79474(18) 0.07497(11) 0.77179(9) 0.0215(3) Uani 1 1 d . A .
H5 H 0.7941 0.0866 0.8360 0.026 Uiso 1 1 calc R . .
C6 C 0.61939(19) 0.07782(13) 0.71673(9) 0.0260(3) Uani 1 1 d D . .
H6A H 0.6022 0.1584 0.7270 0.031 Uiso 0.887(6) 1 calc PR A 1
H6B H 0.5125 0.0331 0.7381 0.031 Uiso 0.887(6) 1 calc PR A 1
H6C H 0.5648 0.1425 0.7485 0.031 Uiso 0.113(6) 1 d PR A 2
H6D H 0.5284 0.0055 0.7113 0.031 Uiso 0.113(6) 1 d PR A 2
C7A C 0.6213(3) 0.0290(2) 0.61567(12) 0.0256(5) Uani 0.887(6) 1 d PD A 1
H7A1 H 0.5193 0.0499 0.5810 0.031 Uiso 0.887(6) 1 calc PR A 1
H7A2 H 0.6008 -0.0560 0.6026 0.031 Uiso 0.887(6) 1 calc PR A 1
C8A C 0.8062(3) 0.0758(2) 0.58558(15) 0.0266(6) Uani 0.887(6) 1 d PD A 1
H8A1 H 0.8262 0.1607 0.5983 0.032 Uiso 0.887(6) 1 calc PR A 1
H8A2 H 0.8043 0.0453 0.5190 0.032 Uiso 0.887(6) 1 calc PR A 1
C7B C 0.657(2) 0.0926(18) 0.6186(9) 0.028(4) Uani 0.113(6) 1 d PD A 2
H7B1 H 0.5377 0.0763 0.5795 0.034 Uiso 0.113(6) 1 calc PR A 2
H7B2 H 0.7188 0.1731 0.6227 0.034 Uiso 0.113(6) 1 calc PR A 2
C8B C 0.778(2) 0.0132(19) 0.5761(12) 0.043(6) Uani 0.113(6) 1 d PD A 2
H8B1 H 0.7987 0.0231 0.5142 0.052 Uiso 0.113(6) 1 calc PR A 2
H8B2 H 0.7165 -0.0676 0.5707 0.052 Uiso 0.113(6) 1 calc PR A 2
C9 C 0.9646(2) 0.04104(14) 0.63609(9) 0.0276(3) Uani 1 1 d D . .
H9A H 0.9656 -0.0408 0.6090 0.033 Uiso 0.887(6) 1 calc PR A 1
H9B H 1.0840 0.0873 0.6273 0.033 Uiso 0.887(6) 1 calc PR A 1
H9C H 1.0321 -0.0221 0.6162 0.033 Uiso 0.113(6) 1 d PR A 2
H9D H 1.0403 0.1121 0.6261 0.033 Uiso 0.113(6) 1 d PR A 2
O3 O 0.98520(13) 0.75467(8) 0.84782(6) 0.0268(2) Uani 1 1 d . . .
O4 O 0.80338(14) 0.66424(8) 0.93265(6) 0.0255(2) Uani 1 1 d . . .
H1O4 H 0.920(3) 0.6683(16) 0.9661(13) 0.060(6) Uiso 1 1 d . . .
C10 C 0.83142(19) 0.70753(11) 0.86092(9) 0.0221(3) Uani 1 1 d . . .
C11 C 0.65756(19) 0.69086(12) 0.79912(9) 0.0243(3) Uani 1 1 d . . .
H11A H 0.5685 0.7305 0.8336 0.029 Uiso 1 1 calc R . .
H11B H 0.6017 0.6077 0.7808 0.029 Uiso 1 1 calc R . .
C12 C 0.68281(19) 0.73472(13) 0.71333(10) 0.0266(3) Uani 1 1 d . . .
H12A H 0.7344 0.8185 0.7311 0.032 Uiso 1 1 calc R . .
H12B H 0.7737 0.6966 0.6791 0.032 Uiso 1 1 calc R . .
C13 C 0.50415(19) 0.71284(12) 0.65216(9) 0.0239(3) Uani 1 1 d . . .
C14 C 0.4866(2) 0.65827(14) 0.56472(10) 0.0341(4) Uani 1 1 d . . .
H14 H 0.5918 0.6320 0.5412 0.041 Uiso 1 1 calc R . .
C15 C 0.3118(2) 0.63487(16) 0.50004(11) 0.0441(5) Uani 1 1 d . . .
H15A H 0.2886 0.5541 0.4637 0.053 Uiso 1 1 calc R . .
H15B H 0.3291 0.6856 0.4573 0.053 Uiso 1 1 calc R . .
C16 C 0.1445(2) 0.65503(14) 0.54995(11) 0.0373(4) Uani 1 1 d . . .
H16A H 0.1023 0.5898 0.5775 0.045 Uiso 1 1 calc R . .
H16B H 0.0414 0.6595 0.5063 0.045 Uiso 1 1 calc R . .
C17 C 0.1941(2) 0.76611(13) 0.62414(10) 0.0281(3) Uani 1 1 d . . .
H17A H 0.0823 0.7808 0.6540 0.034 Uiso 1 1 calc R . .
H17B H 0.2382 0.8311 0.5966 0.034 Uiso 1 1 calc R . .
C18 C 0.34474(19) 0.75849(13) 0.69477(9) 0.0261(3) Uani 1 1 d . . .
H18A H 0.3925 0.8359 0.7353 0.031 Uiso 1 1 calc R . .
H18B H 0.2901 0.7076 0.7328 0.031 Uiso 1 1 calc R . .
O5 O 0.11047(13) 0.66613(9) 0.02970(7) 0.0284(2) Uani 1 1 d . . .
O6 O 0.29850(14) 0.76291(8) -0.04870(7) 0.0279(3) Uani 1 1 d . . .
H1O6 H 0.184(3) 0.7621(18) -0.0816(14) 0.075(7) Uiso 1 1 d . . .
C19 C 0.26641(19) 0.70861(11) 0.01683(9) 0.0211(3) Uani 1 1 d . . .
C20 C 0.43746(19) 0.70517(12) 0.07365(9) 0.0223(3) Uani 1 1 d . . .
H20A H 0.4910 0.7837 0.1109 0.027 Uiso 1 1 calc R . .
H20B H 0.5301 0.6806 0.0329 0.027 Uiso 1 1 calc R . .
C21 C 0.40240(19) 0.62393(12) 0.13684(10) 0.0246(3) Uani 1 1 d . . .
H21A H 0.3146 0.6509 0.1796 0.029 Uiso 1 1 calc R . .
H21B H 0.3428 0.5462 0.0998 0.029 Uiso 1 1 calc R . .
C22 C 0.57627(19) 0.61567(11) 0.19100(9) 0.0223(3) Uani 1 1 d . . .
C23 C 0.5951(2) 0.63832(12) 0.28135(10) 0.0279(3) Uani 1 1 d . . .
H23 H 0.4952 0.6626 0.3119 0.034 Uiso 1 1 calc R . .
C24 C 0.7627(2) 0.62847(14) 0.33899(10) 0.0337(4) Uani 1 1 d . . .
H24A H 0.7309 0.5611 0.3654 0.040 Uiso 1 1 calc R . .
H24B H 0.7982 0.6980 0.3900 0.040 Uiso 1 1 calc R . .
C25 C 0.9274(2) 0.61523(13) 0.28433(10) 0.0316(4) Uani 1 1 d . . .
H25A H 0.9860 0.6910 0.2752 0.038 Uiso 1 1 calc R . .
H25B H 1.0211 0.5873 0.3188 0.038 Uiso 1 1 calc R . .
C26 C 0.8648(2) 0.53096(13) 0.19235(10) 0.0284(3) Uani 1 1 d . . .
H26A H 0.8053 0.4553 0.2013 0.034 Uiso 1 1 calc R . .
H26B H 0.9738 0.5206 0.1587 0.034 Uiso 1 1 calc R . .
C27 C 0.7275(2) 0.57621(13) 0.13727(9) 0.0275(3) Uani 1 1 d . . .
H27A H 0.7955 0.6414 0.1160 0.033 Uiso 1 1 calc R . .
H27B H 0.6703 0.5147 0.0827 0.033 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 0.0033 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'
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
C1 O2 H1O2 108.5(11) . . ?
O1 C1 O2 122.51(12) . . ?
O1 C1 C2 124.05(12) . . ?
O2 C1 C2 113.43(12) . . ?
C1 C2 C3 113.13(11) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C2 116.48(11) . . ?
C4 C3 H3A 108.2 . . ?
C2 C3 H3A 108.2 . . ?
C4 C3 H3B 108.2 . . ?
C2 C3 H3B 108.2 . . ?
H3A C3 H3B 107.3 . . ?
C5 C4 C3 125.10(12) . . ?
C5 C4 C9 121.21(12) . . ?
C3 C4 C9 113.69(11) . . ?
C4 C5 C6 124.43(12) . . ?
C4 C5 H5 117.8 . . ?
C6 C5 H5 117.8 . . ?
C5 C6 C7A 112.52(13) . . ?
C5 C6 C7B 111.3(6) . . ?
C7A C6 C7B 28.5(7) . . ?
C5 C6 H6A 109.1 . . ?
C7A C6 H6A 109.1 . . ?
C7B C6 H6A 83.6 . . ?
C5 C6 H6B 109.1 . . ?
C7A C6 H6B 109.1 . . ?
C7B C6 H6B 131.2 . . ?
H6A C6 H6B 107.8 . . ?
C5 C6 H6C 109.4 . . ?
C7A C6 H6C 129.8 . . ?
C7B C6 H6C 109.4 . . ?
H6A C6 H6C 28.7 . . ?
H6B C6 H6C 81.1 . . ?
C5 C6 H6D 109.4 . . ?
C7A C6 H6D 82.9 . . ?
C7B C6 H6D 109.3 . . ?
H6A C6 H6D 130.7 . . ?
H6B C6 H6D 29.3 . . ?
H6C C6 H6D 108.0 . . ?
C6 C7A C8A 110.28(19) . . ?
C6 C7A H7A1 109.6 . . ?
C8A C7A H7A1 109.6 . . ?
C6 C7A H7A2 109.6 . . ?
C8A C7A H7A2 109.6 . . ?
H7A1 C7A H7A2 108.1 . . ?
C7A C8A C9 110.36(18) . . ?
C7A C8A H8A1 109.6 . . ?
C9 C8A H8A1 109.6 . . ?
C7A C8A H8A2 109.6 . . ?
C9 C8A H8A2 109.6 . . ?
H8A1 C8A H8A2 108.1 . . ?
C8B C7B C6 111.2(13) . . ?
C8B C7B H7B1 109.4 . . ?
C6 C7B H7B1 109.4 . . ?
C8B C7B H7B2 109.4 . . ?
C6 C7B H7B2 109.4 . . ?
H7B1 C7B H7B2 108.0 . . ?
C7B C8B C9 108.9(14) . . ?
C7B C8B H8B1 109.9 . . ?
C9 C8B H8B1 109.9 . . ?
C7B C8B H8B2 109.9 . . ?
C9 C8B H8B2 109.9 . . ?
H8B1 C8B H8B2 108.3 . . ?
C4 C9 C8A 113.30(13) . . ?
C4 C9 C8B 114.9(7) . . ?
C8A C9 C8B 27.6(8) . . ?
C4 C9 H9A 108.9 . . ?
C8A C9 H9A 108.9 . . ?
C8B C9 H9A 83.1 . . ?
C4 C9 H9B 108.9 . . ?
C8A C9 H9B 108.9 . . ?
C8B C9 H9B 128.2 . . ?
H9A C9 H9B 107.7 . . ?
C4 C9 H9C 108.4 . . ?
C8A C9 H9C 130.2 . . ?
C8B C9 H9C 108.6 . . ?
H9A C9 H9C 29.0 . . ?
H9B C9 H9C 81.1 . . ?
C4 C9 H9D 108.4 . . ?
C8A C9 H9D 84.3 . . ?
C8B C9 H9D 108.8 . . ?
H9A C9 H9D 130.5 . . ?
H9B C9 H9D 28.1 . . ?
H9C C9 H9D 107.5 . . ?
C10 O4 H1O4 109.5(11) . . ?
O3 C10 O4 122.62(13) . . ?
O3 C10 C11 124.83(12) . . ?
O4 C10 C11 112.55(12) . . ?
C10 C11 C12 114.85(12) . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.5 . . ?
C13 C12 C11 112.68(12) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 122.38(13) . . ?
C14 C13 C18 121.09(13) . . ?
C12 C13 C18 116.52(12) . . ?
C13 C14 C15 124.70(14) . . ?
C13 C14 H14 117.6 . . ?
C15 C14 H14 117.6 . . ?
C14 C15 C16 112.03(13) . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 C17 110.15(13) . . ?
C15 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C16 C17 C18 110.46(12) . . ?
C16 C17 H17A 109.6 . . ?
C18 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
C18 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C13 C18 C17 112.54(12) . . ?
C13 C18 H18A 109.1 . . ?
C17 C18 H18A 109.1 . . ?
C13 C18 H18B 109.1 . . ?
C17 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C19 O6 H1O6 109.2(13) . . ?
O5 C19 O6 122.78(12) . . ?
O5 C19 C20 123.27(12) . . ?
O6 C19 C20 113.94(12) . . ?
C19 C20 C21 113.23(11) . . ?
C19 C20 H20A 108.9 . . ?
C21 C20 H20A 108.9 . . ?
C19 C20 H20B 108.9 . . ?
C21 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C22 C21 C20 113.43(11) . . ?
C22 C21 H21A 108.9 . . ?
C20 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
C20 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C23 C22 C21 122.32(13) . . ?
C23 C22 C27 121.03(13) . . ?
C21 C22 C27 116.62(12) . . ?
C22 C23 C24 124.80(14) . . ?
C22 C23 H23 117.6 . . ?
C24 C23 H23 117.6 . . ?
C23 C24 C25 112.10(12) . . ?
C23 C24 H24A 109.2 . . ?
C25 C24 H24A 109.2 . . ?
C23 C24 H24B 109.2 . . ?
C25 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
C26 C25 C24 110.58(12) . . ?
C26 C25 H25A 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 108.1 . . ?
C25 C26 C27 109.79(12) . . ?
C25 C26 H26A 109.7 . . ?
C27 C26 H26A 109.7 . . ?
C25 C26 H26B 109.7 . . ?
C27 C26 H26B 109.7 . . ?
H26A C26 H26B 108.2 . . ?
C22 C27 C26 112.86(12) . . ?
C22 C27 H27A 109.0 . . ?
C26 C27 H27A 109.0 . . ?
C22 C27 H27B 109.0 . . ?
C26 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
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
O1 C1 1.2205(16) . ?
O2 C1 1.3261(16) . ?
O2 H1O2 0.94(2) . ?
C1 C2 1.4926(19) . ?
C2 C3 1.5180(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5045(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.3220(19) . ?
C4 C9 1.5102(19) . ?
C5 C6 1.4993(19) . ?
C5 H5 0.9500 . ?
C6 C7A 1.513(2) . ?
C6 C7B 1.574(13) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 H6C 0.9900 . ?
C6 H6D 0.9900 . ?
C7A C8A 1.519(3) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8A C9 1.526(2) . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C7B C8B 1.496(17) . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?
C8B C9 1.534(15) . ?
C8B H8B1 0.9900 . ?
C8B H8B2 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 H9C 0.9900 . ?
C9 H9D 0.9900 . ?
O3 C10 1.2244(16) . ?
O4 C10 1.3231(16) . ?
O4 H1O4 0.96(2) . ?
C10 C11 1.4886(19) . ?
C11 C12 1.5225(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5029(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.326(2) . ?
C13 C18 1.508(2) . ?
C14 C15 1.507(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.515(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.518(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.518(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
O5 C19 1.2191(16) . ?
O6 C19 1.3229(16) . ?
O6 H1O6 0.95(2) . ?
C19 C20 1.4893(19) . ?
C20 C21 1.5266(18) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.5047(19) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.3253(19) . ?
C22 C27 1.506(2) . ?
C23 C24 1.502(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.524(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.517(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.522(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H1O2 O1 0.94(2) 1.72(2) 2.6602(13) 174.6(18) 2_857
O4 H1O4 O5 0.96(2) 1.65(2) 2.6062(14) 174.0(18) 1_656
O6 H1O6 O3 0.95(2) 1.73(2) 2.6735(14) 173.8(19) 1_454
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
O1 C1 C2 C3 -9.63(19) . . . . ?
O2 C1 C2 C3 170.81(11) . . . . ?
C1 C2 C3 C4 173.24(11) . . . . ?
C2 C3 C4 C5 3.9(2) . . . . ?
C2 C3 C4 C9 -175.20(12) . . . . ?
C3 C4 C5 C6 -177.49(13) . . . . ?
C9 C4 C5 C6 1.6(2) . . . . ?
C4 C5 C6 C7A 14.6(2) . . . . ?
C4 C5 C6 C7B -16.2(8) . . . . ?
C5 C6 C7A C8A -45.3(3) . . . . ?
C7B C6 C7A C8A 48.2(12) . . . . ?
C6 C7A C8A C9 61.1(3) . . . . ?
C5 C6 C7B C8B 46.1(18) . . . . ?
C7A C6 C7B C8B -52.1(14) . . . . ?
C6 C7B C8B C9 -60(2) . . . . ?
C5 C4 C9 C8A 14.0(2) . . . . ?
C3 C4 C9 C8A -166.79(15) . . . . ?
C5 C4 C9 C8B -16.2(9) . . . . ?
C3 C4 C9 C8B 162.9(9) . . . . ?
C7A C8A C9 C4 -44.9(3) . . . . ?
C7A C8A C9 C8B 54.7(15) . . . . ?
C7B C8B C9 C4 45(2) . . . . ?
C7B C8B C9 C8A -47.6(13) . . . . ?
O3 C10 C11 C12 1.6(2) . . . . ?
O4 C10 C11 C12 -177.63(12) . . . . ?
C10 C11 C12 C13 178.41(12) . . . . ?
C11 C12 C13 C14 -126.15(15) . . . . ?
C11 C12 C13 C18 55.08(17) . . . . ?
C12 C13 C14 C15 -179.42(15) . . . . ?
C18 C13 C14 C15 -0.7(2) . . . . ?
C13 C14 C15 C16 -13.6(2) . . . . ?
C14 C15 C16 C17 44.15(19) . . . . ?
C15 C16 C17 C18 -62.38(16) . . . . ?
C14 C13 C18 C17 -16.63(19) . . . . ?
C12 C13 C18 C17 162.15(12) . . . . ?
C16 C17 C18 C13 47.63(17) . . . . ?
O5 C19 C20 C21 11.29(19) . . . . ?
O6 C19 C20 C21 -169.25(12) . . . . ?
C19 C20 C21 C22 177.14(11) . . . . ?
C20 C21 C22 C23 123.62(15) . . . . ?
C20 C21 C22 C27 -58.38(16) . . . . ?
C21 C22 C23 C24 178.22(13) . . . . ?
C27 C22 C23 C24 0.3(2) . . . . ?
C22 C23 C24 C25 12.7(2) . . . . ?
C23 C24 C25 C26 -43.29(17) . . . . ?
C24 C25 C26 C27 61.84(16) . . . . ?
C23 C22 C27 C26 17.93(19) . . . . ?
C21 C22 C27 C26 -160.10(12) . . . . ?
C25 C26 C27 C22 -48.34(17) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190132
