#------------------------------------------------------------------------------
#$Date: 2024-07-05 18:08:08 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292926 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/16/1571665.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_1571665
loop_
_publ_author_name
'Song, Yongxiang'
'Wang, Wengui'
'Yang, Jiafan'
'Gao, Dewei'
'Billingsley, John M.'
'Wang, Songtao'
'Zhu, Yiguang'
'Wang, Junfeng'
'Ju, Jianhua'
'Yan, Yan'
'Tang, Yi'
_publ_section_title
;
 β-Terrecyclene synthase constructs the quadrane backbone in
 terrecyclic acid biosynthesis.
;
_journal_issue                   23
_journal_name_full               'Chemical science'
_journal_page_first              8750
_journal_page_last               8755
_journal_paper_doi               10.1039/d4sc01208a
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H22 O3'
_chemical_formula_sum            'C15 H22 O3'
_chemical_formula_weight         250.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2g7x2q
_audit_creation_date             2020-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-06-22 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.989(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.36910(10)
_cell_length_b                   12.0175(2)
_cell_length_c                   9.0830(2)
_cell_measurement_reflns_used    5095
_cell_measurement_temperature    106(2)
_cell_measurement_theta_max      73.8160
_cell_measurement_theta_min      5.1570
_cell_volume                     657.39(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      106(2)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  26.00   0.50    0.50    --    0.00 -82.00  60.00   78
  2  ω    -32.00  27.00   0.50    0.50    --    0.00 -82.00   0.00  118
  3  ω    -13.00  25.00   0.50    0.50    --    0.00 -77.00 120.00   76
  4  ω    -42.00 -15.00   0.50    0.50    --    0.00 -77.00 120.00   54
  5  ω     21.00  55.00   0.50    0.50    --   40.00  65.00 -30.02   68
  6  ω     32.00  69.00   0.50    0.50    --   52.00  75.00  11.86   74
  7  ω     41.00  72.00   0.50    0.50    --   68.00  74.00 -49.07   62
  8  ω    121.00 157.00   0.50    0.50    --   68.00  74.00 -49.07   72
  9  ω     54.00  79.00   0.50    0.50    --   80.00  71.00 -61.26   50
 10  ω     78.00 179.00   0.50    0.50    --   95.80  45.00  60.00  202
 11  ω     77.00 177.00   0.50    0.50    --   95.80  45.00  30.00  200
 12  ω     42.00 125.00   0.50    0.50    --   95.80 -82.00-150.00  166
 13  ω     74.00 117.00   0.50    0.50    --   95.80  54.00  -6.05   86
 14  ω      7.00  39.00   0.50    0.50    --   95.80 -82.00-150.00   64
 15  ω     73.00 132.00   0.50    0.50    --   95.80  61.00 -30.00  118
 16  ω     71.00 161.00   0.50    0.50    --   95.80  68.00 -60.60  180
 17  ω     46.00  86.00   0.50    0.50    --   95.80 -30.00-150.00   80
 18  ω    106.00 184.00   0.50    0.50    --   95.80  30.00 -90.00  156
 19  ω     72.00  97.00   0.50    0.50    --   95.80  61.00 -90.00   50
 20  ω     74.00 180.00   0.50    0.50    --   95.80  61.00 120.00  212
 21  ω     83.00 110.00   0.50    0.50    --   95.80  52.00 -62.70   54
 22  ω    103.00 171.00   0.50    0.50    --   95.80  82.00  90.00  136
 23  ω    121.00 173.00   0.50    0.50    --   95.80  54.00  -6.05  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0312757000
_diffrn_orient_matrix_UB_12      -0.0324910000
_diffrn_orient_matrix_UB_13      0.1699190000
_diffrn_orient_matrix_UB_21      -0.2295963000
_diffrn_orient_matrix_UB_22      0.0491880000
_diffrn_orient_matrix_UB_23      -0.0156952000
_diffrn_orient_matrix_UB_31      -0.1083096000
_diffrn_orient_matrix_UB_32      -0.1138032000
_diffrn_orient_matrix_UB_33      -0.0553840000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6277
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.370
_diffrn_reflns_theta_min         5.150
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       plate
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1132 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2560
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0277
_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)+(0.0422P)²+0.0844P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0737
_reflns_Friedel_coverage         0.858
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                2496
_reflns_number_total             2560
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc01208a2.cif
_cod_data_source_block           songyongxiang_sx-terb2_collect
_cod_depositor_comments
'Adding full bibliography for 1571665--1571666.cif.'
_cod_database_code               1571665
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C28 H44 N2 O6 '
_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_max   0.986
_shelx_estimated_absorpt_t_min   0.903
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C11(H11), C4(H4), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C9(H9A,H9B), C10(H10A,H10B), C3(H3A,H3B)
2.c X=CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
2.e Idealised tetrahedral OH refined as rotating group:
 O17(H17), O13(H13)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.123
_oxdiff_exptl_absorpt_empirical_full_min 0.907
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O17 O 0.9841(2) 0.59979(11) 0.56347(15) 0.0246(3) Uani 1 1 d . . . . .
H17 H 0.9816 0.5385 0.5233 0.037 Uiso 1 1 calc GR . . . .
O14 O 0.8824(2) 0.38781(11) 0.40986(17) 0.0279(3) Uani 1 1 d . . . . .
O13 O 0.6710(2) 0.23725(11) 0.32704(18) 0.0315(3) Uani 1 1 d . . . . .
H13 H 0.7880 0.2047 0.3704 0.047 Uiso 1 1 calc GR . . . .
C1 C 0.4840(3) 0.52881(13) 0.33102(19) 0.0179(4) Uani 1 1 d . . . . .
C5 C 0.5917(3) 0.55293(14) 0.5023(2) 0.0212(4) Uani 1 1 d . . . . .
C7 C 0.7014(3) 0.34616(15) 0.3484(2) 0.0219(4) Uani 1 1 d . . . . .
C2 C 0.6145(3) 0.59745(15) 0.24670(19) 0.0190(3) Uani 1 1 d . . . . .
H2 H 0.7437 0.5544 0.2438 0.023 Uiso 1 1 calc R . . . .
C11 C 0.4463(3) 0.60343(15) 0.0816(2) 0.0216(4) Uani 1 1 d . . . . .
H11 H 0.4902 0.6593 0.0186 0.026 Uiso 1 1 calc R . . . .
C12 C 0.2453(3) 0.58044(14) 0.2650(2) 0.0197(4) Uani 1 1 d . . . . .
H12A H 0.1338 0.5230 0.2525 0.024 Uiso 1 1 calc R . . . .
H12B H 0.2244 0.6363 0.3361 0.024 Uiso 1 1 calc R . . . .
C4 C 0.7623(3) 0.64448(15) 0.5185(2) 0.0236(4) Uani 1 1 d . . . . .
H4 H 0.7511 0.6994 0.5953 0.028 Uiso 1 1 calc R . . . .
C13 C 0.2221(3) 0.63445(15) 0.1041(2) 0.0215(4) Uani 1 1 d . . . . .
C6 C 0.5411(3) 0.50633(17) 0.6185(2) 0.0278(4) Uani 1 1 d . . . . .
H6A H 0.4293 0.4531 0.5979 0.033 Uiso 1 1 calc R . . . .
H6B H 0.6174 0.5268 0.7207 0.033 Uiso 1 1 calc R . . . .
C9 C 0.3771(3) 0.39360(15) 0.1068(2) 0.0244(4) Uani 1 1 d . . . . .
H9A H 0.4217 0.3223 0.0765 0.029 Uiso 1 1 calc R . . . .
H9B H 0.2166 0.3932 0.0787 0.029 Uiso 1 1 calc R . . . .
C8 C 0.4785(3) 0.40546(14) 0.2861(2) 0.0201(4) Uani 1 1 d . . . . .
H8 H 0.3770 0.3681 0.3313 0.024 Uiso 1 1 calc R . . . .
C14 C 0.0165(3) 0.59411(18) -0.0273(2) 0.0266(4) Uani 1 1 d . . . . .
H14A H 0.0205 0.6227 -0.1250 0.040 Uiso 1 1 calc GR . . . .
H14B H -0.1152 0.6202 -0.0087 0.040 Uiso 1 1 calc GR . . . .
H14C H 0.0156 0.5143 -0.0303 0.040 Uiso 1 1 calc GR . . . .
C10 C 0.4447(3) 0.48549(16) 0.0138(2) 0.0254(4) Uani 1 1 d . . . . .
H10A H 0.3428 0.4846 -0.0922 0.030 Uiso 1 1 calc R . . . .
H10B H 0.5918 0.4690 0.0097 0.030 Uiso 1 1 calc R . . . .
C3 C 0.6951(3) 0.69757(15) 0.3565(2) 0.0247(4) Uani 1 1 d . . . . .
H3A H 0.8207 0.7338 0.3385 0.030 Uiso 1 1 calc R . . . .
H3B H 0.5771 0.7516 0.3432 0.030 Uiso 1 1 calc R . . . .
C15 C 0.1940(3) 0.76213(16) 0.1056(2) 0.0286(4) Uani 1 1 d . . . . .
H15A H 0.3279 0.7950 0.1734 0.043 Uiso 1 1 calc GR . . . .
H15B H 0.0726 0.7800 0.1422 0.043 Uiso 1 1 calc GR . . . .
H15C H 0.1640 0.7907 0.0021 0.043 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D4SC01208A 2024
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
C4 O17 H17 109.5 . . ?
C7 O13 H13 109.5 . . ?
C5 C1 C2 105.79(14) . . ?
C5 C1 C12 112.12(14) . . ?
C5 C1 C8 115.01(14) . . ?
C2 C1 C12 102.15(13) . . ?
C8 C1 C2 110.78(14) . . ?
C8 C1 C12 110.14(13) . . ?
C1 C5 C4 108.00(15) . . ?
C6 C5 C1 126.39(17) . . ?
C6 C5 C4 125.55(17) . . ?
O14 C7 O13 123.05(17) . . ?
O14 C7 C8 127.52(16) . . ?
O13 C7 C8 109.43(15) . . ?
C1 C2 H2 108.9 . . ?
C1 C2 C3 102.51(14) . . ?
C11 C2 C1 101.13(13) . . ?
C11 C2 H2 108.9 . . ?
C11 C2 C3 125.14(15) . . ?
C3 C2 H2 108.9 . . ?
C2 C11 H11 111.2 . . ?
C2 C11 C13 105.21(14) . . ?
C2 C11 C10 105.01(14) . . ?
C13 C11 H11 111.2 . . ?
C10 C11 H11 111.2 . . ?
C10 C11 C13 112.70(15) . . ?
C1 C12 H12A 110.1 . . ?
C1 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
C13 C12 C1 107.87(14) . . ?
C13 C12 H12A 110.1 . . ?
C13 C12 H12B 110.1 . . ?
O17 C4 C5 111.21(14) . . ?
O17 C4 H4 109.9 . . ?
O17 C4 C3 111.68(16) . . ?
C5 C4 H4 109.9 . . ?
C5 C4 C3 103.98(14) . . ?
C3 C4 H4 109.9 . . ?
C11 C13 C12 102.25(13) . . ?
C14 C13 C11 114.24(15) . . ?
C14 C13 C12 113.16(15) . . ?
C14 C13 C15 104.38(15) . . ?
C15 C13 C11 110.71(15) . . ?
C15 C13 C12 112.37(16) . . ?
C5 C6 H6A 120.0 . . ?
C5 C6 H6B 120.0 . . ?
H6A C6 H6B 120.0 . . ?
H9A C9 H9B 107.6 . . ?
C8 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C10 C9 C8 114.63(15) . . ?
C1 C8 C9 109.49(14) . . ?
C1 C8 H8 107.0 . . ?
C7 C8 C1 114.51(14) . . ?
C7 C8 C9 111.45(14) . . ?
C7 C8 H8 107.0 . . ?
C9 C8 H8 107.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 C11 114.03(15) . . ?
C9 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C2 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
C4 C3 C2 103.10(14) . . ?
C4 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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
O17 H17 0.8200 . ?
O17 C4 1.441(2) . ?
O14 C7 1.214(2) . ?
O13 H13 0.8200 . ?
O13 C7 1.328(2) . ?
C1 C5 1.510(2) . ?
C1 C2 1.540(2) . ?
C1 C12 1.570(2) . ?
C1 C8 1.535(2) . ?
C5 C4 1.519(3) . ?
C5 C6 1.324(3) . ?
C7 C8 1.524(2) . ?
C2 H2 0.9800 . ?
C2 C11 1.535(2) . ?
C2 C3 1.540(3) . ?
C11 H11 0.9800 . ?
C11 C13 1.553(2) . ?
C11 C10 1.544(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.561(2) . ?
C4 H4 0.9800 . ?
C4 C3 1.532(3) . ?
C13 C14 1.535(2) . ?
C13 C15 1.545(2) . ?
C6 H6A 0.9300 . ?
C6 H6B 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.551(3) . ?
C9 C10 1.535(3) . ?
C8 H8 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O17 C4 C3 C2 83.54(17) . . . . ?
O14 C7 C8 C1 -10.4(3) . . . . ?
O14 C7 C8 C9 114.6(2) . . . . ?
O13 C7 C8 C1 168.99(15) . . . . ?
O13 C7 C8 C9 -66.04(19) . . . . ?
C1 C5 C4 O17 -101.94(16) . . . . ?
C1 C5 C4 C3 18.39(18) . . . . ?
C1 C2 C11 C13 46.18(17) . . . . ?
C1 C2 C11 C10 -72.96(16) . . . . ?
C1 C2 C3 C4 40.52(17) . . . . ?
C1 C12 C13 C11 3.66(18) . . . . ?
C1 C12 C13 C14 127.02(16) . . . . ?
C1 C12 C13 C15 -115.07(16) . . . . ?
C5 C1 C2 C11 -159.36(14) . . . . ?
C5 C1 C2 C3 -29.24(17) . . . . ?
C5 C1 C12 C13 136.71(15) . . . . ?
C5 C1 C8 C7 -50.6(2) . . . . ?
C5 C1 C8 C9 -176.56(15) . . . . ?
C5 C4 C3 C2 -36.47(17) . . . . ?
C2 C1 C5 C4 6.92(18) . . . . ?
C2 C1 C5 C6 -175.68(18) . . . . ?
C2 C1 C12 C13 23.89(17) . . . . ?
C2 C1 C8 C7 69.32(18) . . . . ?
C2 C1 C8 C9 -56.69(17) . . . . ?
C2 C11 C13 C12 -30.46(17) . . . . ?
C2 C11 C13 C14 -153.08(15) . . . . ?
C2 C11 C13 C15 89.44(18) . . . . ?
C2 C11 C10 C9 59.67(19) . . . . ?
C11 C2 C3 C4 153.97(16) . . . . ?
C12 C1 C5 C4 -103.63(16) . . . . ?
C12 C1 C5 C6 73.8(2) . . . . ?
C12 C1 C2 C11 -41.90(16) . . . . ?
C12 C1 C2 C3 88.22(15) . . . . ?
C12 C1 C8 C7 -178.41(14) . . . . ?
C12 C1 C8 C9 55.59(18) . . . . ?
C13 C11 C10 C9 -54.3(2) . . . . ?
C6 C5 C4 O17 80.6(2) . . . . ?
C6 C5 C4 C3 -159.04(18) . . . . ?
C8 C1 C5 C4 129.52(15) . . . . ?
C8 C1 C5 C6 -53.1(2) . . . . ?
C8 C1 C2 C11 75.39(16) . . . . ?
C8 C1 C2 C3 -154.49(14) . . . . ?
C8 C1 C12 C13 -93.86(16) . . . . ?
C8 C9 C10 C11 -41.7(2) . . . . ?
C10 C11 C13 C12 83.41(17) . . . . ?
C10 C11 C13 C14 -39.2(2) . . . . ?
C10 C11 C13 C15 -156.69(15) . . . . ?
C10 C9 C8 C1 38.1(2) . . . . ?
C10 C9 C8 C7 -89.60(18) . . . . ?
C3 C2 C11 C13 -67.9(2) . . . . ?
C3 C2 C11 C10 172.94(17) . . . . ?
