#------------------------------------------------------------------------------
#$Date: 2021-09-06 12:08:28 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268525 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/86/7128635.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_7128635
loop_
_publ_author_name
'Ghosh, Arghya'
'Barik, Shilpa'
'Shee, Sayan'
'Biju, Akkattu T.'
_publ_section_title
;
 Enantioselective synthesis of tetra-substituted tetralines and
 tetrahydro-indolizines by NHC-catalyzed azolium-enolate cascade.
;
_journal_issue                   63
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7794
_journal_page_last               7797
_journal_paper_doi               10.1039/d1cc03165a
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H21 Cl O3'
_chemical_formula_weight         428.89
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-05-13 deposited with the CCDC.	2021-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                107.789(2)
_cell_angle_beta                 95.854(2)
_cell_angle_gamma                110.117(2)
_cell_formula_units_Z            2
_cell_length_a                   8.8163(3)
_cell_length_b                   11.2961(4)
_cell_length_c                   12.0369(4)
_cell_measurement_reflns_used    8430
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.40
_cell_measurement_theta_min      1.926
_cell_volume                     1042.66(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker SMART APEX-II Ultra'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0915
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            36013
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.719
_diffrn_reflns_theta_min         1.826
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.754
_exptl_absorpt_correction_T_min  0.696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       needlelike
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 2839 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     561
_refine_ls_number_reflns         12384
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0572
_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)+(0.0618P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1353
_reflns_Friedel_coverage         0.945
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.926
_reflns_number_gt                8107
_reflns_number_total             12384
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc03165a2.cif
_cod_data_source_block           SB_SC_153
_cod_depositor_comments          'Adding full bibliography for 7128635.cif.'
_cod_original_cell_volume        1042.66(6)
_cod_database_code               7128635
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_xyz
'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 0.78982(13) 0.08361(10) 0.20909(9) 0.0287(3) Uani 1 1 d . . . . .
Cl2 Cl 0.73396(14) 0.54254(11) 0.18777(9) 0.0331(3) Uani 1 1 d . . . . .
O1 O 0.4252(3) 0.4405(3) 0.4330(2) 0.0258(6) Uani 1 1 d . . . . .
O2 O 0.7432(3) 0.3338(3) 0.8704(2) 0.0282(6) Uani 1 1 d . . . . .
O3 O 0.8189(3) 0.4834(3) 0.7841(2) 0.0279(6) Uani 1 1 d . . . . .
O4 O 0.7311(3) 0.8328(3) 0.8627(2) 0.0284(7) Uani 1 1 d . . . . .
O5 O 0.8135(3) 0.9803(3) 0.7756(2) 0.0287(7) Uani 1 1 d . . . . .
O6 O 0.4394(3) 0.9541(3) 0.4323(2) 0.0243(6) Uani 1 1 d . . . . .
C1 C 0.6825(6) 0.1849(4) 0.9776(4) 0.0327(10) Uani 1 1 d . . . . .
H1A H 0.598661 0.105008 0.979930 0.049 Uiso 1 1 calc R U . . .
H1B H 0.701654 0.260473 1.049177 0.049 Uiso 1 1 calc R U . . .
H1C H 0.783619 0.171250 0.972554 0.049 Uiso 1 1 calc R U . . .
C2 C 0.6263(5) 0.2124(4) 0.8715(3) 0.0254(9) Uani 1 1 d . . . . .
C3 C 0.4889(5) 0.1384(4) 0.7867(3) 0.0251(9) Uani 1 1 d . . . . .
H3 H 0.412873 0.061880 0.794136 0.030 Uiso 1 1 calc R U . . .
C4 C 0.4496(4) 0.1719(4) 0.6794(3) 0.0213(8) Uani 1 1 d . . . . .
H4 H 0.406710 0.086255 0.610536 0.026 Uiso 1 1 calc R U . . .
C5 C 0.6120(4) 0.2636(4) 0.6579(3) 0.0213(8) Uani 1 1 d . . . . .
H5 H 0.668437 0.204791 0.623613 0.026 Uiso 1 1 calc R U . . .
C6 C 0.5831(4) 0.3286(4) 0.5665(3) 0.0212(8) Uani 1 1 d . . . . .
H6 H 0.599692 0.421885 0.612594 0.025 Uiso 1 1 calc R U . . .
C7 C 0.4002(4) 0.2550(4) 0.4928(3) 0.0186(8) Uani 1 1 d . . . . .
H7 H 0.376485 0.159009 0.451223 0.022 Uiso 1 1 calc R U . . .
C8 C 0.3764(4) 0.3175(4) 0.4008(3) 0.0201(8) Uani 1 1 d . . . . .
C9 C 0.2911(4) 0.2328(4) 0.2729(3) 0.0223(8) Uani 1 1 d . . . . .
C10 C 0.2310(5) 0.0922(4) 0.2266(4) 0.0265(9) Uani 1 1 d . . . . .
H10 H 0.245767 0.046122 0.276197 0.032 Uiso 1 1 calc R U . . .
C11 C 0.1494(5) 0.0200(4) 0.1070(4) 0.0337(10) Uani 1 1 d . . . . .
H11 H 0.109614 -0.074021 0.076966 0.040 Uiso 1 1 calc R U . . .
C12 C 0.1269(5) 0.0874(5) 0.0322(4) 0.0352(11) Uani 1 1 d . . . . .
H12 H 0.070541 0.038755 -0.047707 0.042 Uiso 1 1 calc R U . . .
C13 C 0.7035(4) 0.3357(4) 0.4855(3) 0.0212(8) Uani 1 1 d . . . . .
C14 C 0.8203(4) 0.4604(4) 0.4948(3) 0.0244(9) Uani 1 1 d . . . . .
H14 H 0.828636 0.539098 0.554424 0.029 Uiso 1 1 calc R U . . .
C15 C 0.9239(5) 0.4682(4) 0.4164(4) 0.0289(10) Uani 1 1 d . . . . .
H15 H 1.000329 0.552348 0.423282 0.035 Uiso 1 1 calc R U . . .
C16 C 0.9158(5) 0.3528(4) 0.3277(3) 0.0250(9) Uani 1 1 d . . . . .
H16 H 0.985688 0.358053 0.274915 0.030 Uiso 1 1 calc R U . . .
C17 C 0.8010(4) 0.2298(4) 0.3199(3) 0.0218(8) Uani 1 1 d . . . . .
C18 C 0.6966(4) 0.2188(4) 0.3975(3) 0.0211(8) Uani 1 1 d . . . . .
H18 H 0.622225 0.134119 0.391200 0.025 Uiso 1 1 calc R U . . .
C19 C 0.7293(4) 0.3702(4) 0.7735(3) 0.0224(8) Uani 1 1 d . . . . .
C20 C 0.3189(4) 0.2284(4) 0.6774(3) 0.0202(8) Uani 1 1 d . . . . .
C21 C 0.2876(4) 0.2675(4) 0.5798(3) 0.0210(8) Uani 1 1 d . . . . .
C22 C 0.1669(4) 0.3179(4) 0.5716(3) 0.0249(9) Uani 1 1 d . . . . .
H22 H 0.146382 0.343559 0.507048 0.030 Uiso 1 1 calc R U . . .
C23 C 0.0755(5) 0.3307(4) 0.6583(4) 0.0279(9) Uani 1 1 d . . . . .
H23 H -0.004645 0.366007 0.652604 0.034 Uiso 1 1 calc R U . . .
C24 C 0.1041(5) 0.2905(4) 0.7539(4) 0.0291(9) Uani 1 1 d . . . . .
H24 H 0.041682 0.297220 0.811539 0.035 Uiso 1 1 calc R U . . .
C25 C 0.2261(5) 0.2405(4) 0.7629(3) 0.0258(9) Uani 1 1 d . . . . .
H25 H 0.245818 0.214651 0.827402 0.031 Uiso 1 1 calc R U . . .
C26 C 0.2719(6) 0.3006(5) 0.1959(4) 0.0298(10) Uani 1 1 d . . . . .
H26 H 0.315047 0.394768 0.224860 0.036 Uiso 1 1 calc R U . . .
C27 C 0.1889(5) 0.2278(5) 0.0768(4) 0.0342(10) Uani 1 1 d . . . . .
H27 H 0.174609 0.273188 0.026508 0.041 Uiso 1 1 calc R U . . .
C28 C 0.1735(6) 0.6147(5) 0.0237(4) 0.0376(11) Uani 1 1 d . . . . .
H28 H 0.124858 0.569715 -0.057882 0.045 Uiso 1 1 calc R U . . .
C29 C 0.2994(7) 0.7429(5) 0.0641(4) 0.0465(14) Uani 1 1 d . . . . .
H29 H 0.338085 0.782855 0.009920 0.056 Uiso 1 1 calc R U . . .
C30 C 0.3669(5) 0.8110(4) 0.1860(3) 0.0333(10) Uani 1 1 d . . . . .
H30 H 0.448410 0.898419 0.213700 0.040 Uiso 1 1 calc R U . . .
C31 C 0.3149(4) 0.7507(4) 0.2666(3) 0.0200(8) Uani 1 1 d . . . . .
C32 C 0.3862(4) 0.8305(4) 0.3964(3) 0.0198(8) Uani 1 1 d . . . . .
C33 C 0.3997(4) 0.7623(4) 0.4860(3) 0.0194(8) Uani 1 1 d . . . . .
H33 H 0.368443 0.665522 0.442140 0.023 Uiso 1 1 calc R U . . .
C34 C 0.5836(4) 0.8262(4) 0.5563(3) 0.0208(8) Uani 1 1 d . . . . .
H34 H 0.610272 0.921989 0.601341 0.025 Uiso 1 1 calc R U . . .
C35 C 0.6063(4) 0.7608(4) 0.6487(3) 0.0211(8) Uani 1 1 d . . . . .
H35 H 0.662438 0.700973 0.616469 0.025 Uiso 1 1 calc R U . . .
C36 C 0.7225(4) 0.8684(4) 0.7652(3) 0.0239(8) Uani 1 1 d . . . . .
C37 C 0.6147(5) 0.7107(4) 0.8626(3) 0.0263(9) Uani 1 1 d . . . . .
C38 C 0.6695(6) 0.6838(5) 0.9697(4) 0.0359(11) Uani 1 1 d . . . . .
H38A H 0.585311 0.604059 0.971858 0.054 Uiso 1 1 calc R U . . .
H38B H 0.687848 0.759643 1.040802 0.054 Uiso 1 1 calc R U . . .
H38C H 0.770818 0.670276 0.965639 0.054 Uiso 1 1 calc R U . . .
C39 C 0.6987(4) 0.8206(4) 0.4708(3) 0.0209(8) Uani 1 1 d . . . . .
C40 C 0.6760(5) 0.6983(4) 0.3838(3) 0.0228(8) Uani 1 1 d . . . . .
H40 H 0.596438 0.617855 0.381932 0.027 Uiso 1 1 calc R U . . .
C41 C 0.7722(5) 0.6965(4) 0.2997(3) 0.0238(8) Uani 1 1 d . . . . .
C42 C 0.8949(5) 0.8135(4) 0.3024(4) 0.0276(9) Uani 1 1 d . . . . .
H42 H 0.959498 0.810799 0.245966 0.033 Uiso 1 1 calc R U . . .
C43 C 0.9200(5) 0.9349(4) 0.3905(4) 0.0271(9) Uani 1 1 d . . . . .
H43 H 1.003173 1.014488 0.393995 0.033 Uiso 1 1 calc R U . . .
C44 C 0.8228(4) 0.9394(4) 0.4736(4) 0.0241(9) Uani 1 1 d . . . . .
H44 H 0.840113 1.021930 0.531793 0.029 Uiso 1 1 calc R U . . .
C45 C 0.2912(4) 0.7792(4) 0.5750(3) 0.0202(8) Uani 1 1 d . . . . .
C46 C 0.3145(4) 0.7325(4) 0.6689(3) 0.0197(8) Uani 1 1 d . . . . .
C47 C 0.2159(5) 0.7403(4) 0.7512(3) 0.0256(9) Uani 1 1 d . . . . .
H47 H 0.228049 0.707187 0.812019 0.031 Uiso 1 1 calc R U . . .
C48 C 0.1006(5) 0.7959(4) 0.7448(4) 0.0273(9) Uani 1 1 d . . . . .
H48 H 0.036003 0.800861 0.801143 0.033 Uiso 1 1 calc R U . . .
C49 C 0.0811(5) 0.8445(4) 0.6544(4) 0.0265(9) Uani 1 1 d . . . . .
H49 H 0.004697 0.883893 0.650627 0.032 Uiso 1 1 calc R U . . .
C50 C 0.1753(4) 0.8346(4) 0.5693(3) 0.0213(8) Uani 1 1 d . . . . .
H50 H 0.159954 0.865767 0.507677 0.026 Uiso 1 1 calc R U . . .
C51 C 0.4415(4) 0.6712(4) 0.6689(3) 0.0212(8) Uani 1 1 d . . . . .
H51 H 0.396430 0.585729 0.599701 0.025 Uiso 1 1 calc R U . . .
C52 C 0.4785(5) 0.6370(4) 0.7765(3) 0.0256(9) Uani 1 1 d . . . . .
H52 H 0.401890 0.560133 0.782954 0.031 Uiso 1 1 calc R U . . .
C53 C 0.1203(5) 0.5536(4) 0.1029(4) 0.0315(10) Uani 1 1 d . . . . .
H53 H 0.035487 0.467655 0.075144 0.038 Uiso 1 1 calc R U . . .
C54 C 0.1926(5) 0.6197(4) 0.2242(3) 0.0279(9) Uani 1 1 d . . . . .
H54 H 0.159656 0.576620 0.277514 0.033 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
C19 O2 C2 120.7(3) . . ?
C36 O4 C37 121.2(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 O2 122.0(3) . . ?
C3 C2 C1 127.6(4) . . ?
O2 C2 C1 110.4(3) . . ?
C2 C3 C4 123.0(3) . . ?
C2 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
C3 C4 C20 116.5(3) . . ?
C3 C4 C5 109.8(3) . . ?
C20 C4 C5 111.6(3) . . ?
C3 C4 H4 106.1 . . ?
C20 C4 H4 106.1 . . ?
C5 C4 H4 106.1 . . ?
C19 C5 C6 110.6(3) . . ?
C19 C5 C4 112.2(3) . . ?
C6 C5 C4 113.9(3) . . ?
C19 C5 H5 106.5 . . ?
C6 C5 H5 106.5 . . ?
C4 C5 H5 106.5 . . ?
C13 C6 C5 113.8(3) . . ?
C13 C6 C7 111.4(3) . . ?
C5 C6 C7 110.2(3) . . ?
C13 C6 H6 107.1 . . ?
C5 C6 H6 107.1 . . ?
C7 C6 H6 107.1 . . ?
C8 C7 C21 112.0(3) . . ?
C8 C7 C6 109.2(3) . . ?
C21 C7 C6 108.1(3) . . ?
C8 C7 H7 109.2 . . ?
C21 C7 H7 109.2 . . ?
C6 C7 H7 109.2 . . ?
O1 C8 C9 119.2(3) . . ?
O1 C8 C7 119.1(3) . . ?
C9 C8 C7 121.7(3) . . ?
C10 C9 C26 118.9(4) . . ?
C10 C9 C8 124.0(3) . . ?
C26 C9 C8 117.2(4) . . ?
C11 C10 C9 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 120.2(4) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C27 119.7(4) . . ?
C11 C12 H12 120.2 . . ?
C27 C12 H12 120.2 . . ?
C14 C13 C18 118.6(4) . . ?
C14 C13 C6 120.3(4) . . ?
C18 C13 C6 121.0(3) . . ?
C15 C14 C13 120.6(4) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 121.1(4) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 118.0(4) . . ?
C17 C16 H16 121.0 . . ?
C15 C16 H16 121.0 . . ?
C16 C17 C18 122.3(4) . . ?
C16 C17 Cl1 118.5(3) . . ?
C18 C17 Cl1 119.2(3) . . ?
C17 C18 C13 119.5(3) . . ?
C17 C18 H18 120.3 . . ?
C13 C18 H18 120.3 . . ?
O3 C19 O2 117.5(3) . . ?
O3 C19 C5 124.6(3) . . ?
O2 C19 C5 117.8(3) . . ?
C25 C20 C21 119.0(4) . . ?
C25 C20 C4 124.0(3) . . ?
C21 C20 C4 116.9(3) . . ?
C22 C21 C20 119.8(4) . . ?
C22 C21 C7 125.1(3) . . ?
C20 C21 C7 115.1(3) . . ?
C21 C22 C23 120.7(4) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C22 C23 C24 119.8(4) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C25 C24 C23 119.7(4) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C20 C25 C24 121.0(4) . . ?
C20 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C27 C26 C9 120.1(4) . . ?
C27 C26 H26 119.9 . . ?
C9 C26 H26 119.9 . . ?
C26 C27 C12 120.4(4) . . ?
C26 C27 H27 119.8 . . ?
C12 C27 H27 119.8 . . ?
C53 C28 C29 120.5(4) . . ?
C53 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C30 C29 C28 119.3(4) . . ?
C30 C29 H29 120.3 . . ?
C28 C29 H29 120.3 . . ?
C31 C30 C29 120.8(4) . . ?
C31 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C30 C31 C54 119.2(3) . . ?
C30 C31 C32 118.5(3) . . ?
C54 C31 C32 122.3(3) . . ?
O6 C32 C31 119.5(3) . . ?
O6 C32 C33 119.0(3) . . ?
C31 C32 C33 121.5(3) . . ?
C45 C33 C32 113.3(3) . . ?
C45 C33 C34 108.7(3) . . ?
C32 C33 C34 107.9(3) . . ?
C45 C33 H33 109.0 . . ?
C32 C33 H33 109.0 . . ?
C34 C33 H33 109.0 . . ?
C39 C34 C35 113.5(3) . . ?
C39 C34 C33 110.8(3) . . ?
C35 C34 C33 110.6(3) . . ?
C39 C34 H34 107.2 . . ?
C35 C34 H34 107.2 . . ?
C33 C34 H34 107.2 . . ?
C36 C35 C34 110.0(3) . . ?
C36 C35 C51 112.2(3) . . ?
C34 C35 C51 114.3(3) . . ?
C36 C35 H35 106.6 . . ?
C34 C35 H35 106.6 . . ?
C51 C35 H35 106.6 . . ?
O5 C36 O4 117.8(3) . . ?
O5 C36 C35 124.7(3) . . ?
O4 C36 C35 117.4(3) . . ?
C52 C37 O4 121.6(3) . . ?
C52 C37 C38 128.2(4) . . ?
O4 C37 C38 110.2(3) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C40 C39 C44 118.8(4) . . ?
C40 C39 C34 120.6(3) . . ?
C44 C39 C34 120.5(4) . . ?
C41 C40 C39 119.8(3) . . ?
C41 C40 H40 120.1 . . ?
C39 C40 H40 120.1 . . ?
C42 C41 C40 121.5(4) . . ?
C42 C41 Cl2 119.9(3) . . ?
C40 C41 Cl2 118.6(3) . . ?
C41 C42 C43 118.7(4) . . ?
C41 C42 H42 120.6 . . ?
C43 C42 H42 120.6 . . ?
C42 C43 C44 120.7(4) . . ?
C42 C43 H43 119.6 . . ?
C44 C43 H43 119.6 . . ?
C43 C44 C39 120.4(4) . . ?
C43 C44 H44 119.8 . . ?
C39 C44 H44 119.8 . . ?
C50 C45 C46 119.4(3) . . ?
C50 C45 C33 125.1(3) . . ?
C46 C45 C33 115.5(3) . . ?
C47 C46 C45 118.7(4) . . ?
C47 C46 C51 124.4(3) . . ?
C45 C46 C51 116.8(3) . . ?
C48 C47 C46 121.3(4) . . ?
C48 C47 H47 119.4 . . ?
C46 C47 H47 119.4 . . ?
C47 C48 C49 119.7(4) . . ?
C47 C48 H48 120.1 . . ?
C49 C48 H48 120.1 . . ?
C48 C49 C50 119.9(4) . . ?
C48 C49 H49 120.0 . . ?
C50 C49 H49 120.0 . . ?
C45 C50 C49 120.8(3) . . ?
C45 C50 H50 119.6 . . ?
C49 C50 H50 119.6 . . ?
C52 C51 C46 115.9(3) . . ?
C52 C51 C35 109.2(3) . . ?
C46 C51 C35 111.6(3) . . ?
C52 C51 H51 106.5 . . ?
C46 C51 H51 106.5 . . ?
C35 C51 H51 106.5 . . ?
C37 C52 C51 123.1(3) . . ?
C37 C52 H52 118.4 . . ?
C51 C52 H52 118.4 . . ?
C28 C53 C54 120.0(4) . . ?
C28 C53 H53 120.0 . . ?
C54 C53 H53 120.0 . . ?
C53 C54 C31 120.1(3) . . ?
C53 C54 H54 119.9 . . ?
C31 C54 H54 119.9 . . ?
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 C17 1.742(4) . ?
Cl2 C41 1.739(4) . ?
O1 C8 1.221(4) . ?
O2 C19 1.358(4) . ?
O2 C2 1.409(4) . ?
O3 C19 1.208(4) . ?
O4 C36 1.355(4) . ?
O4 C37 1.407(4) . ?
O5 C36 1.201(4) . ?
O6 C32 1.223(4) . ?
C1 C2 1.481(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.318(5) . ?
C3 C4 1.493(5) . ?
C3 H3 0.9300 . ?
C4 C20 1.498(5) . ?
C4 C5 1.552(5) . ?
C4 H4 0.9800 . ?
C5 C19 1.511(5) . ?
C5 C6 1.542(5) . ?
C5 H5 0.9800 . ?
C6 C13 1.511(5) . ?
C6 C7 1.554(5) . ?
C6 H6 0.9800 . ?
C7 C8 1.518(5) . ?
C7 C21 1.523(5) . ?
C7 H7 0.9800 . ?
C8 C9 1.490(5) . ?
C9 C10 1.391(6) . ?
C9 C26 1.403(6) . ?
C10 C11 1.386(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(6) . ?
C11 H11 0.9300 . ?
C12 C27 1.388(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.393(5) . ?
C13 C18 1.395(5) . ?
C14 C15 1.380(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(5) . ?
C18 H18 0.9300 . ?
C20 C25 1.382(5) . ?
C20 C21 1.410(5) . ?
C21 C22 1.377(6) . ?
C22 C23 1.385(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.389(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.385(6) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C27 1.385(6) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C53 1.370(6) . ?
C28 C29 1.386(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.384(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.377(5) . ?
C30 H30 0.9300 . ?
C31 C54 1.394(5) . ?
C31 C32 1.482(5) . ?
C32 C33 1.521(5) . ?
C33 C45 1.519(5) . ?
C33 C34 1.552(5) . ?
C33 H33 0.9800 . ?
C34 C39 1.521(5) . ?
C34 C35 1.544(5) . ?
C34 H34 0.9800 . ?
C35 C36 1.518(5) . ?
C35 C51 1.551(5) . ?
C35 H35 0.9800 . ?
C37 C52 1.319(5) . ?
C37 C38 1.483(5) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 C40 1.388(5) . ?
C39 C44 1.397(5) . ?
C40 C41 1.385(5) . ?
C40 H40 0.9300 . ?
C41 C42 1.379(5) . ?
C42 C43 1.382(6) . ?
C42 H42 0.9300 . ?
C43 C44 1.382(6) . ?
C43 H43 0.9300 . ?
C44 H44 0.9300 . ?
C45 C50 1.376(5) . ?
C45 C46 1.411(5) . ?
C46 C47 1.386(5) . ?
C46 C51 1.505(5) . ?
C47 C48 1.374(6) . ?
C47 H47 0.9300 . ?
C48 C49 1.381(5) . ?
C48 H48 0.9300 . ?
C49 C50 1.385(6) . ?
C49 H49 0.9300 . ?
C50 H50 0.9300 . ?
C51 C52 1.496(5) . ?
C51 H51 0.9800 . ?
C52 H52 0.9300 . ?
C53 C54 1.382(5) . ?
C53 H53 0.9300 . ?
C54 H54 0.9300 . ?
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
_geom_hbond_publ_flag
C7 H7 O6 0.98 2.51 3.398(5) 150.5 1_545 yes
C18 H18 O6 0.93 2.35 3.248(4) 163.7 1_545 yes
C40 H40 O1 0.93 2.35 3.258(4) 164.6 . yes
C7 H7 O6 0.98 2.51 3.398(5) 150.5 1_545 yes
C18 H18 O6 0.93 2.35 3.248(4) 163.7 1_545 yes
C40 H40 O1 0.93 2.35 3.258(4) 164.6 . yes
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
C19 O2 C2 C3 -8.9(6) . . . . ?
C19 O2 C2 C1 171.0(4) . . . . ?
O2 C2 C3 C4 3.7(7) . . . . ?
C1 C2 C3 C4 -176.2(4) . . . . ?
C2 C3 C4 C20 -106.1(5) . . . . ?
C2 C3 C4 C5 22.0(6) . . . . ?
C3 C4 C5 C19 -41.1(4) . . . . ?
C20 C4 C5 C19 89.7(4) . . . . ?
C3 C4 C5 C6 -167.7(3) . . . . ?
C20 C4 C5 C6 -37.0(4) . . . . ?
C19 C5 C6 C13 90.8(4) . . . . ?
C4 C5 C6 C13 -141.7(3) . . . . ?
C19 C5 C6 C7 -143.3(3) . . . . ?
C4 C5 C6 C7 -15.8(4) . . . . ?
C13 C6 C7 C8 -50.9(4) . . . . ?
C5 C6 C7 C8 -178.1(3) . . . . ?
C13 C6 C7 C21 -173.0(3) . . . . ?
C5 C6 C7 C21 59.8(4) . . . . ?
C21 C7 C8 O1 70.6(4) . . . . ?
C6 C7 C8 O1 -49.1(5) . . . . ?
C21 C7 C8 C9 -107.8(4) . . . . ?
C6 C7 C8 C9 132.5(4) . . . . ?
O1 C8 C9 C10 179.8(4) . . . . ?
C7 C8 C9 C10 -1.8(6) . . . . ?
O1 C8 C9 C26 0.1(5) . . . . ?
C7 C8 C9 C26 178.5(4) . . . . ?
C26 C9 C10 C11 -1.8(6) . . . . ?
C8 C9 C10 C11 178.5(4) . . . . ?
C9 C10 C11 C12 0.1(7) . . . . ?
C10 C11 C12 C27 1.1(7) . . . . ?
C5 C6 C13 C14 -112.2(4) . . . . ?
C7 C6 C13 C14 122.5(4) . . . . ?
C5 C6 C13 C18 70.0(4) . . . . ?
C7 C6 C13 C18 -55.2(5) . . . . ?
C18 C13 C14 C15 1.8(5) . . . . ?
C6 C13 C14 C15 -176.1(3) . . . . ?
C13 C14 C15 C16 -0.7(6) . . . . ?
C14 C15 C16 C17 0.1(6) . . . . ?
C15 C16 C17 C18 -0.5(5) . . . . ?
C15 C16 C17 Cl1 -179.8(3) . . . . ?
C16 C17 C18 C13 1.6(5) . . . . ?
Cl1 C17 C18 C13 -179.2(3) . . . . ?
C14 C13 C18 C17 -2.1(5) . . . . ?
C6 C13 C18 C17 175.7(3) . . . . ?
C2 O2 C19 O3 169.9(4) . . . . ?
C2 O2 C19 C5 -14.2(5) . . . . ?
C6 C5 C19 O3 -16.6(5) . . . . ?
C4 C5 C19 O3 -145.0(4) . . . . ?
C6 C5 C19 O2 167.8(3) . . . . ?
C4 C5 C19 O2 39.4(5) . . . . ?
C3 C4 C20 C25 -5.3(5) . . . . ?
C5 C4 C20 C25 -132.5(4) . . . . ?
C3 C4 C20 C21 176.5(3) . . . . ?
C5 C4 C20 C21 49.3(4) . . . . ?
C25 C20 C21 C22 0.5(5) . . . . ?
C4 C20 C21 C22 178.8(3) . . . . ?
C25 C20 C21 C7 178.0(3) . . . . ?
C4 C20 C21 C7 -3.7(4) . . . . ?
C8 C7 C21 C22 5.6(5) . . . . ?
C6 C7 C21 C22 125.9(4) . . . . ?
C8 C7 C21 C20 -171.7(3) . . . . ?
C6 C7 C21 C20 -51.3(4) . . . . ?
C20 C21 C22 C23 0.0(5) . . . . ?
C7 C21 C22 C23 -177.1(3) . . . . ?
C21 C22 C23 C24 -0.9(6) . . . . ?
C22 C23 C24 C25 1.3(6) . . . . ?
C21 C20 C25 C24 -0.2(5) . . . . ?
C4 C20 C25 C24 -178.3(3) . . . . ?
C23 C24 C25 C20 -0.7(6) . . . . ?
C10 C9 C26 C27 2.4(7) . . . . ?
C8 C9 C26 C27 -177.9(4) . . . . ?
C9 C26 C27 C12 -1.3(7) . . . . ?
C11 C12 C27 C26 -0.5(7) . . . . ?
C53 C28 C29 C30 -2.3(8) . . . . ?
C28 C29 C30 C31 2.5(8) . . . . ?
C29 C30 C31 C54 -0.1(7) . . . . ?
C29 C30 C31 C32 -177.4(4) . . . . ?
C30 C31 C32 O6 25.6(6) . . . . ?
C54 C31 C32 O6 -151.6(4) . . . . ?
C30 C31 C32 C33 -152.5(4) . . . . ?
C54 C31 C32 C33 30.3(5) . . . . ?
O6 C32 C33 C45 67.4(4) . . . . ?
C31 C32 C33 C45 -114.5(4) . . . . ?
O6 C32 C33 C34 -52.9(4) . . . . ?
C31 C32 C33 C34 125.2(4) . . . . ?
C45 C33 C34 C39 -176.1(3) . . . . ?
C32 C33 C34 C39 -52.9(4) . . . . ?
C45 C33 C34 C35 57.1(4) . . . . ?
C32 C33 C34 C35 -179.7(3) . . . . ?
C39 C34 C35 C36 95.7(4) . . . . ?
C33 C34 C35 C36 -139.1(3) . . . . ?
C39 C34 C35 C51 -137.1(3) . . . . ?
C33 C34 C35 C51 -11.9(4) . . . . ?
C37 O4 C36 O5 171.7(4) . . . . ?
C37 O4 C36 C35 -12.1(6) . . . . ?
C34 C35 C36 O5 -16.4(6) . . . . ?
C51 C35 C36 O5 -144.9(4) . . . . ?
C34 C35 C36 O4 167.7(3) . . . . ?
C51 C35 C36 O4 39.2(5) . . . . ?
C36 O4 C37 C52 -11.1(6) . . . . ?
C36 O4 C37 C38 169.4(4) . . . . ?
C35 C34 C39 C40 70.2(4) . . . . ?
C33 C34 C39 C40 -54.9(4) . . . . ?
C35 C34 C39 C44 -113.7(4) . . . . ?
C33 C34 C39 C44 121.2(4) . . . . ?
C44 C39 C40 C41 -2.0(5) . . . . ?
C34 C39 C40 C41 174.1(3) . . . . ?
C39 C40 C41 C42 2.1(5) . . . . ?
C39 C40 C41 Cl2 -177.1(3) . . . . ?
C40 C41 C42 C43 -0.7(6) . . . . ?
Cl2 C41 C42 C43 178.4(3) . . . . ?
C41 C42 C43 C44 -0.8(6) . . . . ?
C42 C43 C44 C39 0.9(6) . . . . ?
C40 C39 C44 C43 0.5(5) . . . . ?
C34 C39 C44 C43 -175.6(3) . . . . ?
C32 C33 C45 C50 7.9(5) . . . . ?
C34 C33 C45 C50 127.7(3) . . . . ?
C32 C33 C45 C46 -172.5(3) . . . . ?
C34 C33 C45 C46 -52.6(4) . . . . ?
C50 C45 C46 C47 1.8(5) . . . . ?
C33 C45 C46 C47 -177.8(3) . . . . ?
C50 C45 C46 C51 179.1(3) . . . . ?
C33 C45 C46 C51 -0.5(4) . . . . ?
C45 C46 C47 C48 -2.0(5) . . . . ?
C51 C46 C47 C48 -179.0(3) . . . . ?
C46 C47 C48 C49 0.4(6) . . . . ?
C47 C48 C49 C50 1.3(5) . . . . ?
C46 C45 C50 C49 -0.2(5) . . . . ?
C33 C45 C50 C49 179.4(3) . . . . ?
C48 C49 C50 C45 -1.3(5) . . . . ?
C47 C46 C51 C52 -9.7(5) . . . . ?
C45 C46 C51 C52 173.2(3) . . . . ?
C47 C46 C51 C35 -135.6(3) . . . . ?
C45 C46 C51 C35 47.3(4) . . . . ?
C36 C35 C51 C52 -42.4(4) . . . . ?
C34 C35 C51 C52 -168.6(3) . . . . ?
C36 C35 C51 C46 87.1(4) . . . . ?
C34 C35 C51 C46 -39.1(4) . . . . ?
O4 C37 C52 C51 4.1(7) . . . . ?
C38 C37 C52 C51 -176.5(4) . . . . ?
C46 C51 C52 C37 -103.9(5) . . . . ?
C35 C51 C52 C37 23.2(6) . . . . ?
C29 C28 C53 C54 -0.3(8) . . . . ?
C28 C53 C54 C31 2.7(7) . . . . ?
C30 C31 C54 C53 -2.5(6) . . . . ?
C32 C31 C54 C53 174.7(4) . . . . ?
