#------------------------------------------------------------------------------
#$Date: 2024-07-05 16:22:54 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292796 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/29/7132969.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_7132969
loop_
_publ_author_name
'Kelsey, Shaun R.'
'Griaznov, Georgii'
'Spaeth, Andrew D.'
'Janzen, Daron E.'
'Douglas, Justin T.'
'Thompson, Ward H.'
'Barybin, Mikhail V.'
_publ_section_title
;
 Tuning the redox profile of the 6,6'-biazulenic platform through
 functionalization along its molecular axis.
;
_journal_issue                   39
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5213
_journal_page_last               5216
_journal_paper_doi               10.1039/d4cc00656a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C32 H28 Cl2 O8'
_chemical_formula_sum            'C32 H28 Cl2 O8'
_chemical_formula_weight         611.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-10-12 deposited with the CCDC.	2024-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                96.395(7)
_cell_angle_beta                 99.389(7)
_cell_angle_gamma                117.914(8)
_cell_formula_units_Z            2
_cell_length_a                   9.9510(8)
_cell_length_b                   10.5842(9)
_cell_length_c                   14.9945(12)
_cell_measurement_reflns_used    5126
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      32.4000
_cell_measurement_theta_min      2.2320
_cell_volume                     1344.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00    7.00    --   30.00  54.00 120.00  193
  2  ω    -74.00 119.00   1.00    7.00    --   30.00  54.00-120.00  193
  3  ω    -74.00 112.00   1.00    7.00    --   30.00  54.00 -30.00  186
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0726122000
_diffrn_orient_matrix_UB_12      0.0360223000
_diffrn_orient_matrix_UB_13      -0.0123410000
_diffrn_orient_matrix_UB_21      -0.0186220000
_diffrn_orient_matrix_UB_22      0.0531216000
_diffrn_orient_matrix_UB_23      -0.0136413000
_diffrn_orient_matrix_UB_31      0.0361045000
_diffrn_orient_matrix_UB_32      0.0437229000
_diffrn_orient_matrix_UB_33      0.0455220000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18156
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_min         2.230
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.64a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: pentane'
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         8070
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0731P)²+0.5097P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1598
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5915
_reflns_number_total             8070
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc00656a2.cif
_cod_data_source_block           3a
_cod_depositor_comments          'Adding full bibliography for 7132969.cif.'
_cod_database_code               7132969
_publ_section.title
;Tuning the redox profile of the 6,6'-biazulenic platform
 through functionalization along its molecular axis and 
the surprising structural influence of dichloro substitution
;
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C32H28Cl2O8
_chemical_oxdiff_usercomment     'Misha UK sample SK-3-178'
_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.
;
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C12(H12A,H12B), C21(H21A,H21B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C5(H5), C8'(H8'), C7'(H7'), C7(H7), C4'(H4'), C5'(H5')
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C19(H19A,H19B,H19C), C22(H22A,H22B,H22C), C16(H16A,H16B,
 H16C)
;
_olex2_exptl_crystal_mounting_method 'Mitigen micromount'
_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 1.334
_oxdiff_exptl_absorpt_empirical_full_min 0.787
loop_
_space_group_symop_operation_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_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
Cl1 Cl 1.41477(5) 0.50329(5) 1.09520(3) 0.03169(13) Uani 1 1 d . . . . .
Cl2 Cl -0.02567(7) 0.15538(6) 0.36584(4) 0.04564(16) Uani 1 1 d . . . . .
O6 O 0.00224(16) -0.09833(15) 0.35530(10) 0.0348(3) Uani 1 1 d . . . . .
O4 O 1.16324(16) 0.23242(16) 1.10608(10) 0.0355(3) Uani 1 1 d . . . . .
O2 O 1.47580(16) 0.77617(15) 1.03834(9) 0.0352(3) Uani 1 1 d . . . . .
O1 O 1.41898(17) 0.74217(17) 0.88558(10) 0.0387(4) Uani 1 1 d . . . . .
O8 O 0.29264(18) 0.56988(16) 0.57050(10) 0.0364(3) Uani 1 1 d . . . . .
O7 O 0.11934(18) 0.46557(17) 0.43625(10) 0.0368(3) Uani 1 1 d . . . . .
O3 O 0.91946(18) 0.1439(2) 1.03390(14) 0.0602(6) Uani 1 1 d . . . . .
O5 O 0.2094(2) -0.1051(2) 0.42195(14) 0.0630(6) Uani 1 1 d . . . . .
C3 C 1.1072(2) 0.35434(19) 1.00076(12) 0.0233(3) Uani 1 1 d . . . . .
C10 C 1.0120(2) 0.37032(19) 0.92831(11) 0.0222(3) Uani 1 1 d . . . . .
C9' C 0.3655(2) 0.3383(2) 0.55325(12) 0.0240(3) Uani 1 1 d . . . . .
C9 C 1.1093(2) 0.50163(19) 0.89956(11) 0.0225(3) Uani 1 1 d . . . . .
C1' C 0.2403(2) 0.3420(2) 0.49807(12) 0.0255(4) Uani 1 1 d . . . . .
C10' C 0.3414(2) 0.1928(2) 0.52725(12) 0.0254(3) Uani 1 1 d . . . . .
C4 C 0.8553(2) 0.2774(2) 0.89149(12) 0.0256(3) Uani 1 1 d . . . . .
H4 H 0.808372 0.197173 0.920309 0.031 Uiso 1 1 calc R U . . .
C1 C 1.2592(2) 0.56374(19) 0.95704(12) 0.0235(3) Uani 1 1 d . . . . .
C20 C 0.2096(2) 0.4623(2) 0.49671(12) 0.0269(4) Uani 1 1 d . . . . .
C6 C 0.7833(2) 0.3816(2) 0.76311(12) 0.0244(3) Uani 1 1 d . . . . .
C2 C 1.2565(2) 0.47341(19) 1.01707(11) 0.0225(3) Uani 1 1 d . . . . .
C8 C 1.0653(2) 0.5578(2) 0.82953(12) 0.0252(3) Uani 1 1 d . . . . .
H8 H 1.146552 0.647039 0.821523 0.030 Uiso 1 1 calc R U . . .
C11 C 1.3916(2) 0.7010(2) 0.95417(13) 0.0266(4) Uani 1 1 d . . . . .
C6' C 0.6468(2) 0.3468(2) 0.68830(12) 0.0258(4) Uani 1 1 d . . . . .
C14 C 1.0524(2) 0.2340(2) 1.04673(13) 0.0288(4) Uani 1 1 d . . . . .
C5 C 0.7563(2) 0.2829(2) 0.81940(13) 0.0278(4) Uani 1 1 d . . . . .
H5 H 0.650864 0.205313 0.805923 0.033 Uiso 1 1 calc R U . . .
C8' C 0.4906(2) 0.4528(2) 0.61820(12) 0.0268(4) Uani 1 1 d . . . . .
H8' H 0.491746 0.543567 0.622619 0.032 Uiso 1 1 calc R U . . .
C7' C 0.6130(2) 0.4569(2) 0.67724(13) 0.0279(4) Uani 1 1 d . . . . .
H7' H 0.685868 0.549667 0.716578 0.034 Uiso 1 1 calc R U . . .
C7 C 0.9225(2) 0.5054(2) 0.76942(12) 0.0268(4) Uani 1 1 d . . . . .
H7 H 0.919517 0.563157 0.725796 0.032 Uiso 1 1 calc R U . . .
C2' C 0.1436(2) 0.2036(2) 0.44150(12) 0.0266(4) Uani 1 1 d . . . . .
C3' C 0.2027(2) 0.1109(2) 0.45689(12) 0.0273(4) Uani 1 1 d . . . . .
C4' C 0.4332(2) 0.1393(2) 0.56561(13) 0.0298(4) Uani 1 1 d . . . . .
H4' H 0.400440 0.040704 0.538754 0.036 Uiso 1 1 calc R U . . .
C17 C 0.1410(2) -0.0393(2) 0.41174(13) 0.0317(4) Uani 1 1 d . . . . .
C5' C 0.5648(2) 0.2064(2) 0.63661(13) 0.0308(4) Uani 1 1 d . . . . .
H5' H 0.606713 0.145561 0.653002 0.037 Uiso 1 1 calc R U . . .
C18 C -0.0632(2) -0.2462(2) 0.30735(14) 0.0351(4) Uani 1 1 d . . . . .
H18A H -0.086564 -0.312187 0.351465 0.042 Uiso 1 1 calc R U . . .
H18B H 0.011859 -0.256520 0.275378 0.042 Uiso 1 1 calc R U . . .
C12 C 1.6192(2) 0.9076(2) 1.04767(15) 0.0377(5) Uani 1 1 d . . . . .
H12A H 1.604511 0.966568 1.004201 0.045 Uiso 1 1 calc R U . . .
H12B H 1.700956 0.885214 1.034532 0.045 Uiso 1 1 calc R U . . .
C21 C 0.2634(3) 0.6901(2) 0.57379(16) 0.0378(5) Uani 1 1 d . . . . .
H21A H 0.156286 0.659325 0.581674 0.045 Uiso 1 1 calc R U . . .
H21B H 0.272821 0.726233 0.515747 0.045 Uiso 1 1 calc R U . . .
C15 C 1.1162(3) 0.1115(2) 1.15007(16) 0.0403(5) Uani 1 1 d . . . . .
H15A H 1.061606 0.018521 1.103085 0.048 Uiso 1 1 calc R U . . .
H15B H 1.043497 0.111352 1.187994 0.048 Uiso 1 1 calc R U . . .
C13 C 1.6648(3) 0.9880(2) 1.14438(16) 0.0417(5) Uani 1 1 d . . . . .
H13A H 1.587031 1.016298 1.154797 0.062 Uiso 1 1 calc R U . . .
H13B H 1.767904 1.075915 1.156044 0.062 Uiso 1 1 calc R U . . .
H13C H 1.669887 0.924954 1.186478 0.062 Uiso 1 1 calc R U . . .
C19 C -0.2086(3) -0.2842(3) 0.23944(16) 0.0448(6) Uani 1 1 d . . . . .
H19A H -0.182747 -0.225342 0.192349 0.067 Uiso 1 1 calc R U . . .
H19B H -0.277527 -0.264244 0.271089 0.067 Uiso 1 1 calc R U . . .
H19C H -0.262116 -0.388377 0.209753 0.067 Uiso 1 1 calc R U . . .
C22 C 0.3811(3) 0.8054(3) 0.65314(16) 0.0448(5) Uani 1 1 d . . . . .
H22A H 0.485670 0.841718 0.641596 0.067 Uiso 1 1 calc R U . . .
H22B H 0.377434 0.765363 0.709111 0.067 Uiso 1 1 calc R U . . .
H22C H 0.358538 0.886145 0.661612 0.067 Uiso 1 1 calc R U . . .
C16 C 1.2575(3) 0.1258(3) 1.20889(18) 0.0454(5) Uani 1 1 d . . . . .
H16A H 1.331024 0.131152 1.171230 0.068 Uiso 1 1 calc R U . . .
H16B H 1.228961 0.040656 1.237348 0.068 Uiso 1 1 calc R U . . .
H16C H 1.307083 0.215139 1.257448 0.068 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.1484 0.1585 '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
C17 O6 C18 116.59(16) . . ?
C14 O4 C15 116.42(16) . . ?
C11 O2 C12 118.03(16) . . ?
C20 O8 C21 115.34(15) . . ?
C10 C3 C14 124.08(16) . . ?
C2 C3 C10 107.09(16) . . ?
C2 C3 C14 128.83(16) . . ?
C3 C10 C9 107.57(15) . . ?
C4 C10 C3 126.11(17) . . ?
C4 C10 C9 126.31(16) . . ?
C1' C9' C10' 106.88(15) . . ?
C8' C9' C1' 126.74(17) . . ?
C8' C9' C10' 126.36(16) . . ?
C1 C9 C10 107.00(15) . . ?
C8 C9 C10 127.37(16) . . ?
C8 C9 C1 125.63(17) . . ?
C9' C1' C20 128.93(16) . . ?
C2' C1' C9' 107.15(16) . . ?
C2' C1' C20 123.92(16) . . ?
C3' C10' C9' 108.38(15) . . ?
C4' C10' C9' 126.73(16) . . ?
C4' C10' C3' 124.85(17) . . ?
C10 C4 H4 115.2 . . ?
C5 C4 C10 129.54(18) . . ?
C5 C4 H4 115.2 . . ?
C9 C1 C11 124.96(16) . . ?
C2 C1 C9 108.03(16) . . ?
C2 C1 C11 126.99(16) . . ?
O8 C20 C1' 113.10(15) . . ?
O7 C20 O8 122.79(17) . . ?
O7 C20 C1' 124.11(17) . . ?
C5 C6 C6' 115.26(16) . . ?
C7 C6 C6' 118.21(16) . . ?
C7 C6 C5 126.53(16) . . ?
C3 C2 Cl1 125.84(14) . . ?
C1 C2 Cl1 123.86(14) . . ?
C1 C2 C3 110.27(15) . . ?
C9 C8 H8 115.0 . . ?
C7 C8 C9 130.09(18) . . ?
C7 C8 H8 115.0 . . ?
O2 C11 C1 110.89(16) . . ?
O1 C11 O2 124.41(18) . . ?
O1 C11 C1 124.67(17) . . ?
C7' C6' C6 117.49(16) . . ?
C5' C6' C6 116.41(16) . . ?
C5' C6' C7' 126.10(17) . . ?
O4 C14 C3 114.20(16) . . ?
O3 C14 O4 121.71(18) . . ?
O3 C14 C3 124.09(18) . . ?
C4 C5 C6 130.83(18) . . ?
C4 C5 H5 114.6 . . ?
C6 C5 H5 114.6 . . ?
C9' C8' H8' 114.8 . . ?
C7' C8' C9' 130.40(18) . . ?
C7' C8' H8' 114.8 . . ?
C6' C7' H7' 115.2 . . ?
C8' C7' C6' 129.63(18) . . ?
C8' C7' H7' 115.2 . . ?
C6 C7 H7 115.4 . . ?
C8 C7 C6 129.28(17) . . ?
C8 C7 H7 115.4 . . ?
C1' C2' Cl2 123.85(14) . . ?
C3' C2' Cl2 124.74(14) . . ?
C3' C2' C1' 111.39(15) . . ?
C10' C3' C17 124.78(17) . . ?
C2' C3' C10' 106.19(16) . . ?
C2' C3' C17 129.02(16) . . ?
C10' C4' H4' 115.2 . . ?
C5' C4' C10' 129.66(18) . . ?
C5' C4' H4' 115.2 . . ?
O6 C17 C3' 114.29(16) . . ?
O5 C17 O6 121.62(19) . . ?
O5 C17 C3' 124.07(18) . . ?
C6' C5' H5' 114.6 . . ?
C4' C5' C6' 130.86(18) . . ?
C4' C5' H5' 114.6 . . ?
O6 C18 H18A 110.2 . . ?
O6 C18 H18B 110.2 . . ?
O6 C18 C19 107.51(18) . . ?
H18A C18 H18B 108.5 . . ?
C19 C18 H18A 110.2 . . ?
C19 C18 H18B 110.2 . . ?
O2 C12 H12A 110.5 . . ?
O2 C12 H12B 110.5 . . ?
O2 C12 C13 106.15(18) . . ?
H12A C12 H12B 108.7 . . ?
C13 C12 H12A 110.5 . . ?
C13 C12 H12B 110.5 . . ?
O8 C21 H21A 110.3 . . ?
O8 C21 H21B 110.3 . . ?
O8 C21 C22 106.92(17) . . ?
H21A C21 H21B 108.6 . . ?
C22 C21 H21A 110.3 . . ?
C22 C21 H21B 110.3 . . ?
O4 C15 H15A 110.1 . . ?
O4 C15 H15B 110.1 . . ?
O4 C15 C16 107.80(18) . . ?
H15A C15 H15B 108.5 . . ?
C16 C15 H15A 110.1 . . ?
C16 C15 H15B 110.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
Cl1 C2 1.6738(17) . ?
Cl2 C2' 1.6817(18) . ?
O6 C17 1.306(2) . ?
O6 C18 1.426(2) . ?
O4 C14 1.308(2) . ?
O4 C15 1.421(2) . ?
O2 C11 1.317(2) . ?
O2 C12 1.423(2) . ?
O1 C11 1.184(2) . ?
O8 C20 1.320(2) . ?
O8 C21 1.429(2) . ?
O7 C20 1.183(2) . ?
O3 C14 1.180(2) . ?
O5 C17 1.186(2) . ?
C3 C10 1.400(2) . ?
C3 C2 1.384(2) . ?
C3 C14 1.436(3) . ?
C10 C9 1.437(2) . ?
C10 C4 1.366(2) . ?
C9' C1' 1.398(2) . ?
C9' C10' 1.440(3) . ?
C9' C8' 1.376(2) . ?
C9 C1 1.391(2) . ?
C9 C8 1.372(2) . ?
C1' C20 1.443(3) . ?
C1' C2' 1.389(2) . ?
C10' C3' 1.403(2) . ?
C10' C4' 1.368(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.365(2) . ?
C1 C2 1.379(2) . ?
C1 C11 1.445(3) . ?
C6 C6' 1.478(2) . ?
C6 C5 1.372(3) . ?
C6 C7 1.369(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.368(2) . ?
C6' C7' 1.374(3) . ?
C6' C5' 1.370(3) . ?
C5 H5 0.9500 . ?
C8' H8' 0.9500 . ?
C8' C7' 1.364(2) . ?
C7' H7' 0.9500 . ?
C7 H7 0.9500 . ?
C2' C3' 1.381(2) . ?
C3' C17 1.440(3) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.363(2) . ?
C5' H5' 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.475(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.477(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.470(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.464(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
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
Cl2 C2' C3' C10' -177.69(15) . . . . ?
Cl2 C2' C3' C17 2.8(3) . . . . ?
C3 C10 C9 C1 -1.75(19) . . . . ?
C3 C10 C9 C8 178.71(17) . . . . ?
C3 C10 C4 C5 -177.65(19) . . . . ?
C10 C3 C2 Cl1 -178.22(13) . . . . ?
C10 C3 C2 C1 -0.3(2) . . . . ?
C10 C3 C14 O4 173.50(17) . . . . ?
C10 C3 C14 O3 -7.2(3) . . . . ?
C10 C9 C1 C2 1.56(19) . . . . ?
C10 C9 C1 C11 -177.14(16) . . . . ?
C10 C9 C8 C7 -0.8(3) . . . . ?
C10 C4 C5 C6 -0.1(4) . . . . ?
C9' C1' C20 O8 -15.9(3) . . . . ?
C9' C1' C20 O7 164.2(2) . . . . ?
C9' C1' C2' Cl2 177.79(14) . . . . ?
C9' C1' C2' C3' -0.9(2) . . . . ?
C9' C10' C3' C2' -0.7(2) . . . . ?
C9' C10' C3' C17 178.83(18) . . . . ?
C9' C10' C4' C5' 1.2(4) . . . . ?
C9' C8' C7' C6' 0.3(4) . . . . ?
C9 C10 C4 C5 2.0(3) . . . . ?
C9 C1 C2 Cl1 177.16(13) . . . . ?
C9 C1 C2 C3 -0.8(2) . . . . ?
C9 C1 C11 O2 140.24(18) . . . . ?
C9 C1 C11 O1 -38.1(3) . . . . ?
C9 C8 C7 C6 0.3(3) . . . . ?
C1' C9' C10' C3' 0.2(2) . . . . ?
C1' C9' C10' C4' -177.86(19) . . . . ?
C1' C9' C8' C7' 176.8(2) . . . . ?
C1' C2' C3' C10' 1.0(2) . . . . ?
C1' C2' C3' C17 -178.5(2) . . . . ?
C10' C9' C1' C20 -179.78(18) . . . . ?
C10' C9' C1' C2' 0.5(2) . . . . ?
C10' C9' C8' C7' -5.1(3) . . . . ?
C10' C3' C17 O6 173.09(18) . . . . ?
C10' C3' C17 O5 -8.7(4) . . . . ?
C10' C4' C5' C6' -2.4(4) . . . . ?
C4 C10 C9 C1 178.51(17) . . . . ?
C4 C10 C9 C8 -1.0(3) . . . . ?
C1 C9 C8 C7 179.71(18) . . . . ?
C20 O8 C21 C22 -172.2(2) . . . . ?
C20 C1' C2' Cl2 -2.0(3) . . . . ?
C20 C1' C2' C3' 179.28(17) . . . . ?
C6 C6' C7' C8' -175.81(19) . . . . ?
C6 C6' C5' C4' 178.0(2) . . . . ?
C2 C3 C10 C9 1.27(19) . . . . ?
C2 C3 C10 C4 -179.00(17) . . . . ?
C2 C3 C14 O4 -6.6(3) . . . . ?
C2 C3 C14 O3 172.8(2) . . . . ?
C2 C1 C11 O2 -38.2(3) . . . . ?
C2 C1 C11 O1 143.4(2) . . . . ?
C8 C9 C1 C2 -178.90(17) . . . . ?
C8 C9 C1 C11 2.4(3) . . . . ?
C11 O2 C12 C13 164.69(18) . . . . ?
C11 C1 C2 Cl1 -4.2(3) . . . . ?
C11 C1 C2 C3 177.86(17) . . . . ?
C6' C6 C5 C4 176.97(19) . . . . ?
C6' C6 C7 C8 -177.36(18) . . . . ?
C14 O4 C15 C16 176.6(2) . . . . ?
C14 C3 C10 C9 -178.81(16) . . . . ?
C14 C3 C10 C4 0.9(3) . . . . ?
C14 C3 C2 Cl1 1.9(3) . . . . ?
C14 C3 C2 C1 179.77(18) . . . . ?
C5 C6 C6' C7' 131.49(19) . . . . ?
C5 C6 C6' C5' -48.1(2) . . . . ?
C5 C6 C7 C8 1.9(3) . . . . ?
C8' C9' C1' C20 -1.5(3) . . . . ?
C8' C9' C1' C2' 178.79(18) . . . . ?
C8' C9' C10' C3' -178.18(18) . . . . ?
C8' C9' C10' C4' 3.8(3) . . . . ?
C7' C6' C5' C4' -1.6(4) . . . . ?
C7 C6 C6' C7' -49.2(2) . . . . ?
C7 C6 C6' C5' 131.22(19) . . . . ?
C7 C6 C5 C4 -2.3(3) . . . . ?
C2' C1' C20 O8 163.84(18) . . . . ?
C2' C1' C20 O7 -16.0(3) . . . . ?
C2' C3' C17 O6 -7.5(3) . . . . ?
C2' C3' C17 O5 170.7(2) . . . . ?
C3' C10' C4' C5' -176.5(2) . . . . ?
C4' C10' C3' C2' 177.35(19) . . . . ?
C4' C10' C3' C17 -3.1(3) . . . . ?
C17 O6 C18 C19 -172.87(19) . . . . ?
C5' C6' C7' C8' 3.8(3) . . . . ?
C18 O6 C17 O5 0.6(3) . . . . ?
C18 O6 C17 C3' 178.81(18) . . . . ?
C12 O2 C11 O1 -7.7(3) . . . . ?
C12 O2 C11 C1 173.93(17) . . . . ?
C21 O8 C20 O7 1.5(3) . . . . ?
C21 O8 C20 C1' -178.34(17) . . . . ?
C15 O4 C14 O3 3.7(3) . . . . ?
C15 O4 C14 C3 -176.95(18) . . . . ?
