# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1b
_database_code_depnum_ccdc_archive 'CCDC 2060473'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-02-02 deposited with the CCDC.	2022-02-02 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT094_1b                  
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       2.70 Report
RESPONSE: All highest peaks of the residual electron density
 (0.46-0.31 e/A3) are all located on bonds.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H31 F O2'
_chemical_formula_sum            'C28 H31 F O2'
_chemical_formula_weight         418.53

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   8.14440(10)
_cell_length_b                   14.7371(2)
_cell_length_c                   18.1313(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2176.21(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9173
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      42.91

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7179
_exptl_absorpt_correction_T_max  0.7485
_exptl_absorpt_process_details   
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-Ray tube'
_diffrn_source_power             50
_diffrn_source_current           30
_diffrn_source_size              '0.6 mm, fine-focus'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_reflns_number            155843
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.638
_diffrn_reflns_theta_max         42.104
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             15304
_reflns_number_gt                14387
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    
'SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0553P)²+0.0984P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 6230 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack, Wagner, Acta Cryst., 2013, B69, 249-259).
;
_refine_ls_abs_structure_Flack   0.13(7)
_chemical_absolute_configuration synad
_refine_ls_number_reflns         15304
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0918
_refine_ls_wR_factor_gt          0.0882
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.76278(8) 0.00988(4) 0.68932(4) 0.01561(10) Uani 1 1 d . . . . .
H1A H 0.6624(11) 0.01640(8) 0.7187(3) 0.019 Uiso 1 1 calc R U . . .
H1B H 0.7300(4) 0.00203(9) 0.6377(5) 0.019 Uiso 1 1 calc R U . . .
C2 C 0.85374(9) -0.07541(5) 0.71463(4) 0.01801(11) Uani 1 1 d . . . . .
H2A H 0.8721(2) -0.07225(6) 0.7665(6) 0.022 Uiso 1 1 calc R U . . .
H2B H 0.7876(7) -0.1274(6) 0.70497(11) 0.022 Uiso 1 1 calc R U . . .
C3 C 1.01599(9) -0.08525(5) 0.67550(4) 0.01735(10) Uani 1 1 d . . . . .
O1 O 1.07718(8) -0.15958(4) 0.66189(4) 0.02443(12) Uani 1 1 d . . . . .
C4 C 1.10151(9) -0.00118(5) 0.65699(4) 0.01765(10) Uani 1 1 d . . . . .
H4 H 1.2137(17) -0.00575(8) 0.6353(3) 0.021 Uiso 1 1 calc R U . . .
C5 C 1.03769(8) 0.08229(4) 0.66750(4) 0.01540(9) Uani 1 1 d . . . . .
C6 C 1.14168(8) 0.16462(5) 0.65340(5) 0.02107(13) Uani 1 1 d . . . . .
H6B H 1.2456(12) 0.1456(2) 0.6284(3) 0.025 Uiso 1 1 calc R U . . .
H6A H 1.1716(3) 0.1931(3) 0.7016(5) 0.025 Uiso 1 1 calc R U . . .
C7 C 1.05329(8) 0.23471(5) 0.60533(5) 0.01869(11) Uani 1 1 d . . . . .
H7A H 1.1209(7) 0.2889(6) 0.60088(7) 0.022 Uiso 1 1 calc R U . . .
H7B H 1.0365(2) 0.2100(3) 0.5561(5) 0.022 Uiso 1 1 calc R U . . .
C8 C 0.88774(7) 0.25973(4) 0.63916(4) 0.01360(9) Uani 1 1 d . . . . .
H8 H 0.9054(3) 0.2874(4) 0.6874(7) 0.016 Uiso 1 1 calc R U . . .
C9 C 0.78114(7) 0.17336(4) 0.64819(3) 0.01291(8) Uani 1 1 d . . . . .
H9 H 0.76894(18) 0.1472(3) 0.5978(7) 0.015 Uiso 1 1 calc R U . . .
C10 C 0.86437(8) 0.09787(4) 0.69612(4) 0.01309(8) Uani 1 1 d . . . . .
C11 C 0.60607(8) 0.19598(5) 0.67464(4) 0.01700(10) Uani 1 1 d . . . . .
H11A H 0.61157(10) 0.2153(2) 0.7275(5) 0.020 Uiso 1 1 calc R U . . .
H11B H 0.5381(7) 0.1394(6) 0.67233(5) 0.020 Uiso 1 1 calc R U . . .
C12 C 0.51840(8) 0.27089(5) 0.63014(4) 0.01672(10) Uani 1 1 d . . . . .
H12B H 0.4932(3) 0.2482(2) 0.5798(5) 0.020 Uiso 1 1 calc R U . . .
H12A H 0.4131(11) 0.28679(17) 0.6546(3) 0.020 Uiso 1 1 calc R U . . .
C13 C 0.62698(7) 0.35531(4) 0.62485(4) 0.01348(9) Uani 1 1 d . . . . .
C14 C 0.79175(7) 0.32515(4) 0.59037(4) 0.01351(9) Uani 1 1 d . . . . .
H14 H 0.7614(4) 0.2893(5) 0.5450(6) 0.016 Uiso 1 1 calc R U . . .
C15 C 0.86843(8) 0.41362(5) 0.56164(5) 0.01815(11) Uani 1 1 d . . . . .
H15A H 0.9311(7) 0.4456(3) 0.6009(4) 0.022 Uiso 1 1 calc R U . . .
H15B H 0.9414(8) 0.40247(13) 0.5186(5) 0.022 Uiso 1 1 calc R U . . .
C16 C 0.71603(9) 0.46561(5) 0.53976(4) 0.01677(10) Uani 1 1 d . . . . .
H16 H 0.71615(9) 0.5175(8) 0.5064(5) 0.020 Uiso 1 1 calc R U . . .
C17 C 0.57972(8) 0.43167(4) 0.57193(4) 0.01443(9) Uani 1 1 d . . . . .
C18 C 0.87801(10) 0.12476(5) 0.77836(4) 0.01834(11) Uani 1 1 d . . . . .
H18A H 0.9296(11) 0.1820(6) 0.78230(6) 0.028 Uiso 1 1 calc R U . . .
H18B H 0.9410(11) 0.0808(6) 0.8038(3) 0.028 Uiso 1 1 calc R U . . .
H18C H 0.7718(11) 0.1279(6) 0.7993(2) 0.028 Uiso 1 1 calc R U . . .
C19 C 0.64580(10) 0.40013(5) 0.70129(4) 0.01973(11) Uani 1 1 d . . . . .
H19A H 0.5413(11) 0.4243(6) 0.7169(3) 0.030 Uiso 1 1 calc R U . . .
H19B H 0.7251(12) 0.4487(7) 0.69831(13) 0.030 Uiso 1 1 calc R U . . .
H19C H 0.6828(12) 0.3555(5) 0.7365(4) 0.030 Uiso 1 1 calc R U . . .
C20 C 0.41213(8) 0.46978(4) 0.56699(4) 0.01615(10) Uani 1 1 d . . . . .
O2 O 0.29915(7) 0.43664(4) 0.60303(4) 0.02450(12) Uani 1 1 d . . . . .
C21 C 0.38366(9) 0.54931(5) 0.51797(4) 0.01658(10) Uani 1 1 d . . . . .
H21 H 0.4764(15) 0.5803(5) 0.4957(4) 0.020 Uiso 1 1 calc R U . . .
C22 C 0.23045(9) 0.57839(5) 0.50443(4) 0.01708(10) Uani 1 1 d . . . . .
H22 H 0.1429(14) 0.5456(5) 0.5270(4) 0.020 Uiso 1 1 calc R U . . .
C23 C 0.18554(8) 0.65596(4) 0.45814(4) 0.01518(9) Uani 1 1 d . . . . .
C24 C 0.02575(8) 0.66152(5) 0.42937(4) 0.01746(10) Uani 1 1 d . . . . .
H24 H -0.0530(12) 0.6137(7) 0.44074(18) 0.021 Uiso 1 1 calc R U . . .
C25 C -0.02275(9) 0.73390(5) 0.38493(4) 0.01889(11) Uani 1 1 d . . . . .
H25 H -0.1326(18) 0.73719(7) 0.3650(3) 0.023 Uiso 1 1 calc R U . . .
C26 C 0.09176(10) 0.80082(5) 0.37036(4) 0.01811(11) Uani 1 1 d . . . . .
F1 F 0.04762(8) 0.87314(4) 0.32875(3) 0.02526(10) Uani 1 1 d . . . . .
C27 C 0.25099(10) 0.79806(5) 0.39714(4) 0.01866(11) Uani 1 1 d . . . . .
H27 H 0.3285(12) 0.8461(8) 0.38552(19) 0.022 Uiso 1 1 calc R U . . .
C28 C 0.29737(9) 0.72510(5) 0.44098(4) 0.01720(10) Uani 1 1 d . . . . .
H28 H 0.4054(18) 0.72207(7) 0.4594(3) 0.021 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C2 1.5295(9) . ?
C1 C10 1.5431(9) . ?
C1 H1A 0.980(10) . ?
C1 H1B 0.980(10) . ?
C2 C3 1.5068(11) . ?
C2 H2A 0.953(10) . ?
C2 H2B 0.953(11) . ?
C3 O1 1.2285(9) . ?
C3 C4 1.4604(10) . ?
C4 C5 1.3489(9) . ?
C4 H4 0.997(15) . ?
C5 C6 1.5016(9) . ?
C5 C10 1.5213(9) . ?
C6 C7 1.5313(10) . ?
C6 H6B 1.000(11) . ?
C6 H6A 1.000(11) . ?
C7 C8 1.5265(9) . ?
C7 H7A 0.974(11) . ?
C7 H7B 0.974(11) . ?
C8 C14 1.5242(9) . ?
C8 C9 1.5494(8) . ?
C8 H8 0.977(14) . ?
C9 C11 1.5408(9) . ?
C9 C10 1.5661(8) . ?
C9 H9 0.997(13) . ?
C10 C18 1.5470(10) . ?
C11 C12 1.5425(9) . ?
C11 H11A 1.002(10) . ?
C11 H11B 1.002(10) . ?
C12 C13 1.5294(9) . ?
C12 H12B 0.993(10) . ?
C12 H12A 0.993(10) . ?
C13 C17 1.5282(8) . ?
C13 C19 1.5429(10) . ?
C13 C14 1.5457(9) . ?
C14 C15 1.5367(9) . ?
C14 H14 1.008(14) . ?
C15 C16 1.5116(10) . ?
C15 H15A 0.995(11) . ?
C15 H15B 0.995(11) . ?
C16 C17 1.3501(9) . ?
C16 H16 0.976(15) . ?
C17 C20 1.4787(9) . ?
C18 H18A 0.946(10) . ?
C18 H18B 0.946(9) . ?
C18 H18C 0.946(9) . ?
C19 H19A 0.965(10) . ?
C19 H19B 0.965(10) . ?
C19 H19C 0.965(10) . ?
C20 O2 1.2296(9) . ?
C20 C21 1.4891(9) . ?
C21 C22 1.3420(10) . ?
C21 H21 0.971(15) . ?
C22 C23 1.4646(9) . ?
C22 H22 0.954(15) . ?
C23 C28 1.4017(10) . ?
C23 C24 1.4044(9) . ?
C24 C25 1.3938(10) . ?
C24 H24 0.975(15) . ?
C25 C26 1.3828(11) . ?
C25 H25 0.966(16) . ?
C26 F1 1.3544(8) . ?
C26 C27 1.3853(11) . ?
C27 C28 1.3894(10) . ?
C27 H27 0.971(16) . ?
C28 H28 0.942(16) . ?

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
C2 C1 C10 114.01(5) . . ?
C2 C1 H1A 108.8 . . ?
C10 C1 H1A 108.8 . . ?
C2 C1 H1B 108.8 . . ?
C10 C1 H1B 108.8 . . ?
H1A C1 H1B 107.6 . . ?
C3 C2 C1 111.26(6) . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
O1 C3 C4 121.12(7) . . ?
O1 C3 C2 122.43(7) . . ?
C4 C3 C2 116.41(6) . . ?
C5 C4 C3 123.88(6) . . ?
C5 C4 H4 118.1 . . ?
C3 C4 H4 118.1 . . ?
C4 C5 C6 119.70(6) . . ?
C4 C5 C10 122.91(6) . . ?
C6 C5 C10 117.35(5) . . ?
C5 C6 C7 112.14(6) . . ?
C5 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
H6B C6 H6A 107.9 . . ?
C8 C7 C6 110.45(6) . . ?
C8 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C14 C8 C7 111.88(5) . . ?
C14 C8 C9 107.07(5) . . ?
C7 C8 C9 109.82(5) . . ?
C14 C8 H8 109.3 . . ?
C7 C8 H8 109.3 . . ?
C9 C8 H8 109.3 . . ?
C11 C9 C8 111.94(5) . . ?
C11 C9 C10 112.43(5) . . ?
C8 C9 C10 113.56(5) . . ?
C11 C9 H9 106.1 . . ?
C8 C9 H9 106.1 . . ?
C10 C9 H9 106.1 . . ?
C5 C10 C1 110.09(5) . . ?
C5 C10 C18 107.51(5) . . ?
C1 C10 C18 109.32(5) . . ?
C5 C10 C9 108.64(5) . . ?
C1 C10 C9 108.70(5) . . ?
C18 C10 C9 112.58(5) . . ?
C9 C11 C12 114.86(5) . . ?
C9 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
C9 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.5 . . ?
C13 C12 C11 110.32(5) . . ?
C13 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
H12B C12 H12A 108.1 . . ?
C17 C13 C12 119.52(5) . . ?
C17 C13 C19 105.89(5) . . ?
C12 C13 C19 110.45(6) . . ?
C17 C13 C14 100.16(5) . . ?
C12 C13 C14 107.06(5) . . ?
C19 C13 C14 113.59(5) . . ?
C8 C14 C15 121.67(5) . . ?
C8 C14 C13 113.11(5) . . ?
C15 C14 C13 104.24(5) . . ?
C8 C14 H14 105.5 . . ?
C15 C14 H14 105.5 . . ?
C13 C14 H14 105.5 . . ?
C16 C15 C14 100.68(5) . . ?
C16 C15 H15A 111.6 . . ?
C14 C15 H15A 111.6 . . ?
C16 C15 H15B 111.6 . . ?
C14 C15 H15B 111.6 . . ?
H15A C15 H15B 109.4 . . ?
C17 C16 C15 111.97(6) . . ?
C17 C16 H16 124.0 . . ?
C15 C16 H16 124.0 . . ?
C16 C17 C20 126.31(6) . . ?
C16 C17 C13 109.69(5) . . ?
C20 C17 C13 123.38(6) . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 C17 120.51(6) . . ?
O2 C20 C21 120.88(6) . . ?
C17 C20 C21 118.61(6) . . ?
C22 C21 C20 120.36(6) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 125.90(6) . . ?
C21 C22 H22 117.1 . . ?
C23 C22 H22 117.1 . . ?
C28 C23 C24 118.51(6) . . ?
C28 C23 C22 122.16(6) . . ?
C24 C23 C22 119.33(6) . . ?
C25 C24 C23 121.47(6) . . ?
C25 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
C26 C25 C24 117.71(6) . . ?
C26 C25 H25 121.1 . . ?
C24 C25 H25 121.1 . . ?
F1 C26 C25 119.25(7) . . ?
F1 C26 C27 117.83(7) . . ?
C25 C26 C27 122.92(6) . . ?
C26 C27 C28 118.54(7) . . ?
C26 C27 H27 120.7 . . ?
C28 C27 H27 120.7 . . ?
C27 C28 C23 120.85(6) . . ?
C27 C28 H28 119.6 . . ?
C23 C28 H28 119.6 . . ?

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
C10 C1 C2 C3 -54.10(8) . . . . ?
C1 C2 C3 O1 -149.04(7) . . . . ?
C1 C2 C3 C4 33.46(9) . . . . ?
O1 C3 C4 C5 176.91(8) . . . . ?
C2 C3 C4 C5 -5.56(11) . . . . ?
C3 C4 C5 C6 174.17(7) . . . . ?
C3 C4 C5 C10 -3.49(11) . . . . ?
C4 C5 C6 C7 131.13(7) . . . . ?
C10 C5 C6 C7 -51.07(9) . . . . ?
C5 C6 C7 C8 54.57(9) . . . . ?
C6 C7 C8 C14 -176.57(6) . . . . ?
C6 C7 C8 C9 -57.83(8) . . . . ?
C14 C8 C9 C11 -52.44(7) . . . . ?
C7 C8 C9 C11 -174.11(6) . . . . ?
C14 C8 C9 C10 178.92(5) . . . . ?
C7 C8 C9 C10 57.26(7) . . . . ?
C4 C5 C10 C1 -16.10(9) . . . . ?
C6 C5 C10 C1 166.18(6) . . . . ?
C4 C5 C10 C18 102.89(8) . . . . ?
C6 C5 C10 C18 -74.83(7) . . . . ?
C4 C5 C10 C9 -135.02(7) . . . . ?
C6 C5 C10 C9 47.27(8) . . . . ?
C2 C1 C10 C5 44.61(8) . . . . ?
C2 C1 C10 C18 -73.28(7) . . . . ?
C2 C1 C10 C9 163.48(6) . . . . ?
C11 C9 C10 C5 -178.27(5) . . . . ?
C8 C9 C10 C5 -49.88(7) . . . . ?
C11 C9 C10 C1 61.94(7) . . . . ?
C8 C9 C10 C1 -169.67(5) . . . . ?
C11 C9 C10 C18 -59.32(7) . . . . ?
C8 C9 C10 C18 69.07(7) . . . . ?
C8 C9 C11 C12 50.01(8) . . . . ?
C10 C9 C11 C12 179.24(6) . . . . ?
C9 C11 C12 C13 -51.94(8) . . . . ?
C11 C12 C13 C17 168.95(6) . . . . ?
C11 C12 C13 C19 -67.89(7) . . . . ?
C11 C12 C13 C14 56.25(7) . . . . ?
C7 C8 C14 C15 -52.03(8) . . . . ?
C9 C8 C14 C15 -172.39(6) . . . . ?
C7 C8 C14 C13 -177.30(5) . . . . ?
C9 C8 C14 C13 62.34(7) . . . . ?
C17 C13 C14 C8 169.49(5) . . . . ?
C12 C13 C14 C8 -65.15(7) . . . . ?
C19 C13 C14 C8 57.04(7) . . . . ?
C17 C13 C14 C15 35.29(6) . . . . ?
C12 C13 C14 C15 160.65(6) . . . . ?
C19 C13 C14 C15 -77.16(7) . . . . ?
C8 C14 C15 C16 -162.31(6) . . . . ?
C13 C14 C15 C16 -33.09(7) . . . . ?
C14 C15 C16 C17 18.50(8) . . . . ?
C15 C16 C17 C20 175.34(7) . . . . ?
C15 C16 C17 C13 4.15(8) . . . . ?
C12 C13 C17 C16 -141.12(7) . . . . ?
C19 C13 C17 C16 93.52(7) . . . . ?
C14 C13 C17 C16 -24.76(7) . . . . ?
C12 C13 C17 C20 47.37(9) . . . . ?
C19 C13 C17 C20 -77.98(8) . . . . ?
C14 C13 C17 C20 163.74(6) . . . . ?
C16 C17 C20 O2 -174.76(8) . . . . ?
C13 C17 C20 O2 -4.70(11) . . . . ?
C16 C17 C20 C21 4.83(11) . . . . ?
C13 C17 C20 C21 174.88(6) . . . . ?
O2 C20 C21 C22 -9.20(11) . . . . ?
C17 C20 C21 C22 171.22(7) . . . . ?
C20 C21 C22 C23 179.32(7) . . . . ?
C21 C22 C23 C28 -20.22(12) . . . . ?
C21 C22 C23 C24 159.38(7) . . . . ?
C28 C23 C24 C25 -0.27(11) . . . . ?
C22 C23 C24 C25 -179.88(7) . . . . ?
C23 C24 C25 C26 -0.44(11) . . . . ?
C24 C25 C26 F1 -178.52(7) . . . . ?
C24 C25 C26 C27 0.80(11) . . . . ?
F1 C26 C27 C28 178.90(7) . . . . ?
C25 C26 C27 C28 -0.43(11) . . . . ?
C26 C27 C28 C23 -0.32(11) . . . . ?
C24 C23 C28 C27 0.66(11) . . . . ?
C22 C23 C28 C27 -179.74(7) . . . . ?

_refine_diff_density_max         0.464
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.049


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3g
_database_code_depnum_ccdc_archive 'CCDC 2060484'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-04-27 deposited with the CCDC.	2022-02-02 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT431_3g                  
;
PROBLEM: Short Inter HL..A Contact Br1 .. O2 .. 3.25 Ang.
RESPONSE: This is an intrinsic crystal packing effect.
;
_vrf_PLAT933_3g                  
;
PROBLEM: Number of OMIT Records in Embedded .res File ...          1 Note 
RESPONSE: Reflection 1 0 1 was affected by the beamstop and, therefore,
removed from the refinement. 
;
_vrf_PLAT910_3g                  
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).          3 Note 
RESPONSE: Reflections 0 1 1, 0 0 2, 0 1 4 were behind the beamstop. 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H33 Br O2'
_chemical_formula_sum            'C28 H33 Br O2'
_chemical_formula_weight         481.45

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.6737(2)
_cell_length_b                   13.7426(3)
_cell_length_c                   17.4902(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2325.18(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9968
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      32.09

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.31
_exptl_absorpt_coefficient_mu    1.790
_shelx_estimated_absorpt_T_min   0.527
_shelx_estimated_absorpt_T_max   0.607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4910
_exptl_absorpt_correction_T_max  0.5979
_exptl_absorpt_process_details   
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-Ray tube'
_diffrn_source_power             50
_diffrn_source_current           30
_diffrn_source_size              '0.6 mm, fine-focus'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            76577
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.575
_diffrn_reflns_theta_max         33.749
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9291
_reflns_number_gt                8270
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    
'SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²+0.3819P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3333 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         9291
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0781
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
Br1 Br 1.09393(2) 1.01195(2) 0.67803(2) 0.02980(6) Uani 1 1 d . . . . .
O1 O -0.2269(2) 0.24178(14) 0.65059(14) 0.0476(5) Uani 1 1 d . . . . .
O2 O 0.62301(16) 0.55779(11) 0.72882(10) 0.0292(3) Uani 1 1 d . . . . .
C1 C 0.0938(2) 0.31688(13) 0.56769(11) 0.0232(3) Uani 1 1 d . . . . .
H1A H 0.1579(13) 0.2928(5) 0.5307(7) 0.028 Uiso 1 1 calc R U . . .
H1B H 0.1339(8) 0.3078(2) 0.6171(10) 0.028 Uiso 1 1 calc R U . . .
C2 C -0.0394(2) 0.25756(14) 0.56270(13) 0.0275(4) Uani 1 1 d . . . . .
H2A H -0.0757(8) 0.26047(15) 0.5102(11) 0.033 Uiso 1 1 calc R U . . .
H2B H -0.0194(5) 0.1890(15) 0.5748(3) 0.033 Uiso 1 1 calc R U . . .
C3 C -0.1463(2) 0.29564(15) 0.61720(14) 0.0291(4) Uani 1 1 d . . . . .
C4 C -0.1507(2) 0.40131(15) 0.62679(13) 0.0255(4) Uani 1 1 d . . . . .
H4 H -0.223(2) 0.4286(9) 0.6561(9) 0.031 Uiso 1 1 calc R U . . .
C5 C -0.0569(2) 0.46132(14) 0.59594(11) 0.0212(3) Uani 1 1 d . . . . .
C6 C -0.0765(2) 0.57010(14) 0.60055(12) 0.0246(4) Uani 1 1 d . . . . .
H6B H -0.1589(16) 0.5850(3) 0.6365(7) 0.030 Uiso 1 1 calc R U . . .
H6A H -0.1012(5) 0.5964(5) 0.5468(10) 0.030 Uiso 1 1 calc R U . . .
C7 C 0.0516(2) 0.62310(13) 0.62988(11) 0.0208(3) Uani 1 1 d . . . . .
H7A H 0.0372(3) 0.6930(14) 0.62532(14) 0.025 Uiso 1 1 calc R U . . .
H7B H 0.0643(3) 0.6081(3) 0.6839(10) 0.025 Uiso 1 1 calc R U . . .
C8 C 0.1818(2) 0.59504(13) 0.58634(11) 0.0198(3) Uani 1 1 d . . . . .
H8 H 0.1739(3) 0.6200(7) 0.5301(15) 0.024 Uiso 1 1 calc R U . . .
C9 C 0.19922(19) 0.48271(14) 0.58579(10) 0.0203(3) Uani 1 1 d . . . . .
H9 H 0.2074(3) 0.4639(5) 0.6381(15) 0.024 Uiso 1 1 calc R U . . .
C10 C 0.0715(2) 0.42661(13) 0.55404(10) 0.0212(3) Uani 1 1 d . . . . .
C11 C 0.3349(2) 0.45193(16) 0.54753(13) 0.0267(4) Uani 1 1 d . . . . .
H11A H 0.3304(2) 0.4677(4) 0.4936(11) 0.032 Uiso 1 1 calc R U . . .
H11B H 0.3451(3) 0.3820(15) 0.55206(15) 0.032 Uiso 1 1 calc R U . . .
C12 C 0.4625(2) 0.50146(14) 0.58252(13) 0.0270(4) Uani 1 1 d . . . . .
H12B H 0.4753(3) 0.4785(5) 0.6355(11) 0.032 Uiso 1 1 calc R U . . .
H12A H 0.5454(17) 0.4834(4) 0.5530(6) 0.032 Uiso 1 1 calc R U . . .
C13 C 0.4460(2) 0.61220(14) 0.58227(12) 0.0222(3) Uani 1 1 d . . . . .
C14 C 0.3101(2) 0.63893(13) 0.62323(11) 0.0194(3) Uani 1 1 d . . . . .
H14 H 0.3163(3) 0.6096(8) 0.6750(14) 0.023 Uiso 1 1 calc R U . . .
C15 C 0.3197(2) 0.75002(14) 0.63521(12) 0.0222(3) Uani 1 1 d . . . . .
H15B H 0.2699(10) 0.7701(4) 0.6836(9) 0.027 Uiso 1 1 calc R U . . .
H15A H 0.2775(8) 0.7860(7) 0.5904(9) 0.027 Uiso 1 1 calc R U . . .
C16 C 0.4782(2) 0.77200(14) 0.64147(12) 0.0214(3) Uani 1 1 d . . . . .
H16 H 0.5072(8) 0.8189(13) 0.6009(11) 0.026 Uiso 1 1 calc R U . . .
C17 C 0.5496(2) 0.67243(14) 0.62955(12) 0.0219(3) Uani 1 1 d . . . . .
H17 H 0.639040 0.680237 0.601541 0.026 Uiso 1 1 calc R U . . .
C18 C 0.5743(2) 0.63564(14) 0.71167(12) 0.0233(3) Uani 1 1 d . . . . .
C19 C 0.5293(2) 0.71313(15) 0.76794(12) 0.0249(4) Uani 1 1 d . . . . .
H19A H 0.5961(13) 0.71787(18) 0.8114(9) 0.030 Uiso 1 1 calc R U . . .
H19B H 0.4354(19) 0.6983(3) 0.7888(4) 0.030 Uiso 1 1 calc R U . . .
C20 C 0.5273(2) 0.80768(14) 0.72171(11) 0.0219(3) Uani 1 1 d . . . . .
H20 H 0.459(2) 0.8541(14) 0.7438(7) 0.026 Uiso 1 1 calc R U . . .
C21 C 0.0500(3) 0.44481(16) 0.46751(12) 0.0292(4) Uani 1 1 d . . . . .
H21A H 0.050(2) 0.5207(13) 0.4567(3) 0.044 Uiso 1 1 calc R U . . .
H21B H -0.0459(19) 0.4147(14) 0.4502(4) 0.044 Uiso 1 1 calc R U . . .
H21C H 0.1311(19) 0.4115(14) 0.4364(6) 0.044 Uiso 1 1 calc R U . . .
C22 C 0.4515(3) 0.65077(17) 0.49933(13) 0.0298(4) Uani 1 1 d . . . . .
H22A H 0.435(2) 0.7228(14) 0.49929(17) 0.045 Uiso 1 1 calc R U . . .
H22B H 0.379(2) 0.6176(13) 0.4679(7) 0.045 Uiso 1 1 calc R U . . .
H22C H 0.5450(19) 0.6370(14) 0.4769(6) 0.045 Uiso 1 1 calc R U . . .
C23 C 0.6680(2) 0.85604(14) 0.71522(11) 0.0208(3) Uani 1 1 d . . . . .
C24 C 0.7930(2) 0.80623(14) 0.72387(12) 0.0236(4) Uani 1 1 d . . . . .
H24 H 0.7915(2) 0.739(2) 0.7371(4) 0.028 Uiso 1 1 calc R U . . .
C25 C 0.9197(2) 0.85256(14) 0.71362(11) 0.0244(4) Uani 1 1 d . . . . .
H25 H 1.006(3) 0.8169(11) 0.7205(2) 0.029 Uiso 1 1 calc R U . . .
C26 C 0.9211(2) 0.95007(15) 0.69349(10) 0.0231(3) Uani 1 1 d . . . . .
C27 C 0.7992(2) 1.00231(14) 0.68526(10) 0.0230(3) Uani 1 1 d . . . . .
H27 H 0.8014(2) 1.076(2) 0.6709(4) 0.028 Uiso 1 1 calc R U . . .
C28 C 0.6741(2) 0.95477(14) 0.69645(11) 0.0212(3) Uani 1 1 d . . . . .
H28 H 0.592(2) 0.9895(10) 0.69132(18) 0.025 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Br1 C26 1.895(2) . ?
O1 C3 1.223(3) . ?
O2 C18 1.207(2) . ?
C1 C2 1.527(3) . ?
C1 C10 1.542(3) . ?
C1 H1A 0.955(19) . ?
C1 H1B 0.955(19) . ?
C2 C3 1.501(3) . ?
C2 H2A 0.98(2) . ?
C2 H2B 0.98(2) . ?
C3 C4 1.462(3) . ?
C4 C5 1.340(3) . ?
C4 H4 0.95(3) . ?
C5 C6 1.509(3) . ?
C5 C10 1.519(3) . ?
C6 C7 1.526(3) . ?
C6 H6B 1.04(2) . ?
C6 H6A 1.04(2) . ?
C7 C8 1.521(3) . ?
C7 H7A 0.975(19) . ?
C7 H7B 0.975(19) . ?
C8 C14 1.524(3) . ?
C8 C9 1.553(3) . ?
C8 H8 1.04(3) . ?
C9 C11 1.533(3) . ?
C9 C10 1.559(3) . ?
C9 H9 0.95(3) . ?
C10 C21 1.548(3) . ?
C11 C12 1.537(3) . ?
C11 H11A 0.97(2) . ?
C11 H11B 0.97(2) . ?
C12 C13 1.530(3) . ?
C12 H12B 0.99(2) . ?
C12 H12A 0.99(2) . ?
C13 C17 1.541(3) . ?
C13 C14 1.542(3) . ?
C13 C22 1.545(3) . ?
C14 C15 1.544(3) . ?
C14 H14 0.99(3) . ?
C15 C16 1.566(3) . ?
C15 H15B 1.013(19) . ?
C15 H15A 1.013(19) . ?
C16 C17 1.547(3) . ?
C16 C20 1.561(3) . ?
C16 H16 1.00(3) . ?
C17 C18 1.541(3) . ?
C17 H17 1.0000 . ?
C18 C19 1.514(3) . ?
C19 C20 1.530(3) . ?
C19 H19A 1.00(2) . ?
C19 H19B 1.00(2) . ?
C20 C23 1.518(3) . ?
C20 H20 1.00(3) . ?
C21 H21A 1.059(18) . ?
C21 H21B 1.059(19) . ?
C21 H21C 1.059(18) . ?
C22 H22A 1.003(19) . ?
C22 H22B 1.003(19) . ?
C22 H22C 1.003(19) . ?
C23 C28 1.397(3) . ?
C23 C24 1.398(3) . ?
C24 C25 1.393(3) . ?
C24 H24 0.95(3) . ?
C25 C26 1.386(3) . ?
C25 H25 0.98(3) . ?
C26 C27 1.388(3) . ?
C27 C28 1.389(3) . ?
C27 H27 1.05(3) . ?
C28 H28 0.93(3) . ?

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
C2 C1 C10 113.27(18) . . ?
C2 C1 H1A 108.9 . . ?
C10 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
C10 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C3 C2 C1 111.05(17) . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
O1 C3 C4 121.9(2) . . ?
O1 C3 C2 122.1(2) . . ?
C4 C3 C2 116.04(18) . . ?
C5 C4 C3 123.0(2) . . ?
C5 C4 H4 118.5 . . ?
C3 C4 H4 118.5 . . ?
C4 C5 C6 120.18(19) . . ?
C4 C5 C10 123.71(18) . . ?
C6 C5 C10 116.10(17) . . ?
C5 C6 C7 112.85(17) . . ?
C5 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
H6B C6 H6A 107.8 . . ?
C8 C7 C6 112.51(16) . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 C14 111.23(15) . . ?
C7 C8 C9 110.19(15) . . ?
C14 C8 C9 107.90(15) . . ?
C7 C8 H8 109.2 . . ?
C14 C8 H8 109.2 . . ?
C9 C8 H8 109.2 . . ?
C11 C9 C8 111.73(16) . . ?
C11 C9 C10 112.76(15) . . ?
C8 C9 C10 114.05(16) . . ?
C11 C9 H9 105.8 . . ?
C8 C9 H9 105.8 . . ?
C10 C9 H9 105.8 . . ?
C5 C10 C1 110.30(16) . . ?
C5 C10 C21 108.13(17) . . ?
C1 C10 C21 109.17(15) . . ?
C5 C10 C9 108.72(15) . . ?
C1 C10 C9 108.51(17) . . ?
C21 C10 C9 112.02(16) . . ?
C9 C11 C12 113.06(16) . . ?
C9 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
C9 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 110.83(18) . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
H12B C12 H12A 108.1 . . ?
C12 C13 C17 117.71(18) . . ?
C12 C13 C14 108.94(16) . . ?
C17 C13 C14 100.22(15) . . ?
C12 C13 C22 109.88(17) . . ?
C17 C13 C22 107.28(16) . . ?
C14 C13 C22 112.58(18) . . ?
C8 C14 C13 113.81(15) . . ?
C8 C14 C15 119.86(16) . . ?
C13 C14 C15 104.32(15) . . ?
C8 C14 H14 105.9 . . ?
C13 C14 H14 105.9 . . ?
C15 C14 H14 105.9 . . ?
C14 C15 C16 105.01(16) . . ?
C14 C15 H15B 110.7 . . ?
C16 C15 H15B 110.7 . . ?
C14 C15 H15A 110.7 . . ?
C16 C15 H15A 110.7 . . ?
H15B C15 H15A 108.8 . . ?
C17 C16 C20 105.25(16) . . ?
C17 C16 C15 104.91(15) . . ?
C20 C16 C15 114.93(17) . . ?
C17 C16 H16 110.5 . . ?
C20 C16 H16 110.5 . . ?
C15 C16 H16 110.5 . . ?
C13 C17 C18 115.13(16) . . ?
C13 C17 C16 104.89(16) . . ?
C18 C17 C16 103.52(15) . . ?
C13 C17 H17 111.0 . . ?
C18 C17 H17 111.0 . . ?
C16 C17 H17 111.0 . . ?
O2 C18 C19 125.04(19) . . ?
O2 C18 C17 125.66(19) . . ?
C19 C18 C17 109.30(15) . . ?
C18 C19 C20 104.91(16) . . ?
C18 C19 H19A 110.8 . . ?
C20 C19 H19A 110.8 . . ?
C18 C19 H19B 110.8 . . ?
C20 C19 H19B 110.8 . . ?
H19A C19 H19B 108.8 . . ?
C23 C20 C19 113.57(17) . . ?
C23 C20 C16 110.07(16) . . ?
C19 C20 C16 102.25(15) . . ?
C23 C20 H20 110.2 . . ?
C19 C20 H20 110.2 . . ?
C16 C20 H20 110.2 . . ?
C10 C21 H21A 109.5 . . ?
C10 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C10 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C13 C22 H22A 109.5 . . ?
C13 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C13 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C28 C23 C24 117.65(18) . . ?
C28 C23 C20 118.74(17) . . ?
C24 C23 C20 123.55(17) . . ?
C25 C24 C23 121.57(18) . . ?
C25 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C26 C25 C24 118.92(19) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C25 C26 C27 121.20(19) . . ?
C25 C26 Br1 118.62(16) . . ?
C27 C26 Br1 120.18(15) . . ?
C26 C27 C28 118.82(18) . . ?
C26 C27 H27 120.6 . . ?
C28 C27 H27 120.6 . . ?
C27 C28 C23 121.82(18) . . ?
C27 C28 H28 119.1 . . ?
C23 C28 H28 119.1 . . ?

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
C10 C1 C2 C3 -55.9(2) . . . . ?
C1 C2 C3 O1 -144.3(2) . . . . ?
C1 C2 C3 C4 37.0(3) . . . . ?
O1 C3 C4 C5 174.4(2) . . . . ?
C2 C3 C4 C5 -7.0(3) . . . . ?
C3 C4 C5 C6 173.0(2) . . . . ?
C3 C4 C5 C10 -5.9(3) . . . . ?
C4 C5 C6 C7 130.1(2) . . . . ?
C10 C5 C6 C7 -50.8(2) . . . . ?
C5 C6 C7 C8 51.4(2) . . . . ?
C6 C7 C8 C14 -172.76(15) . . . . ?
C6 C7 C8 C9 -53.1(2) . . . . ?
C7 C8 C9 C11 -175.79(16) . . . . ?
C14 C8 C9 C11 -54.2(2) . . . . ?
C7 C8 C9 C10 54.9(2) . . . . ?
C14 C8 C9 C10 176.49(15) . . . . ?
C4 C5 C10 C1 -12.4(3) . . . . ?
C6 C5 C10 C1 168.55(17) . . . . ?
C4 C5 C10 C21 106.9(2) . . . . ?
C6 C5 C10 C21 -72.1(2) . . . . ?
C4 C5 C10 C9 -131.3(2) . . . . ?
C6 C5 C10 C9 49.7(2) . . . . ?
C2 C1 C10 C5 42.9(2) . . . . ?
C2 C1 C10 C21 -75.8(2) . . . . ?
C2 C1 C10 C9 161.85(16) . . . . ?
C11 C9 C10 C5 179.39(17) . . . . ?
C8 C9 C10 C5 -51.8(2) . . . . ?
C11 C9 C10 C1 59.4(2) . . . . ?
C8 C9 C10 C1 -171.77(15) . . . . ?
C11 C9 C10 C21 -61.2(2) . . . . ?
C8 C9 C10 C21 67.6(2) . . . . ?
C8 C9 C11 C12 54.2(2) . . . . ?
C10 C9 C11 C12 -175.82(17) . . . . ?
C9 C11 C12 C13 -54.3(2) . . . . ?
C11 C12 C13 C17 167.86(17) . . . . ?
C11 C12 C13 C14 54.8(2) . . . . ?
C11 C12 C13 C22 -69.0(2) . . . . ?
C7 C8 C14 C13 179.33(16) . . . . ?
C9 C8 C14 C13 58.4(2) . . . . ?
C7 C8 C14 C15 -56.3(2) . . . . ?
C9 C8 C14 C15 -177.22(16) . . . . ?
C12 C13 C14 C8 -59.5(2) . . . . ?
C17 C13 C14 C8 176.30(15) . . . . ?
C22 C13 C14 C8 62.6(2) . . . . ?
C12 C13 C14 C15 168.05(17) . . . . ?
C17 C13 C14 C15 43.89(19) . . . . ?
C22 C13 C14 C15 -69.8(2) . . . . ?
C8 C14 C15 C16 -157.61(17) . . . . ?
C13 C14 C15 C16 -28.8(2) . . . . ?
C14 C15 C16 C17 2.1(2) . . . . ?
C14 C15 C16 C20 -112.97(17) . . . . ?
C12 C13 C17 C18 -47.4(2) . . . . ?
C14 C13 C17 C18 70.45(19) . . . . ?
C22 C13 C17 C18 -171.86(17) . . . . ?
C12 C13 C17 C16 -160.47(17) . . . . ?
C14 C13 C17 C16 -42.62(19) . . . . ?
C22 C13 C17 C16 75.07(19) . . . . ?
C20 C16 C17 C13 147.00(16) . . . . ?
C15 C16 C17 C13 25.3(2) . . . . ?
C20 C16 C17 C18 25.95(19) . . . . ?
C15 C16 C17 C18 -95.70(18) . . . . ?
C13 C17 C18 O2 62.8(3) . . . . ?
C16 C17 C18 O2 176.66(19) . . . . ?
C13 C17 C18 C19 -117.88(18) . . . . ?
C16 C17 C18 C19 -4.0(2) . . . . ?
O2 C18 C19 C20 159.5(2) . . . . ?
C17 C18 C19 C20 -19.8(2) . . . . ?
C18 C19 C20 C23 -83.45(19) . . . . ?
C18 C19 C20 C16 35.1(2) . . . . ?
C17 C16 C20 C23 82.81(18) . . . . ?
C15 C16 C20 C23 -162.30(16) . . . . ?
C17 C16 C20 C19 -38.2(2) . . . . ?
C15 C16 C20 C19 76.7(2) . . . . ?
C19 C20 C23 C28 -160.11(18) . . . . ?
C16 C20 C23 C28 85.9(2) . . . . ?
C19 C20 C23 C24 22.7(3) . . . . ?
C16 C20 C23 C24 -91.3(2) . . . . ?
C28 C23 C24 C25 -0.5(3) . . . . ?
C20 C23 C24 C25 176.71(18) . . . . ?
C23 C24 C25 C26 -0.8(3) . . . . ?
C24 C25 C26 C27 1.5(3) . . . . ?
C24 C25 C26 Br1 -178.98(15) . . . . ?
C25 C26 C27 C28 -1.0(3) . . . . ?
Br1 C26 C27 C28 179.56(14) . . . . ?
C26 C27 C28 C23 -0.4(3) . . . . ?
C24 C23 C28 C27 1.1(3) . . . . ?
C20 C23 C28 C27 -176.25(17) . . . . ?

_refine_diff_density_max         0.671
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.058



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2g
_database_code_depnum_ccdc_archive 'CCDC 2060479'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-04-16 deposited with the CCDC.	2022-02-02 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT910_2g                  
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).          6 Note  
RESPONSE: Six reflections 0 2 0, 0 2 1, 0 2 2, 0 1 1, 0 1 2 and 0 0 2
were behind the beamstop. 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H32 Br Cl O2'
_chemical_formula_sum            'C28 H32 Br Cl O2'
_chemical_formula_weight         515.89

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.4163(2)
_cell_length_b                   24.3559(6)
_cell_length_c                   26.0244(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4700.8(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9819
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      28.06

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_F_000             2144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    1.886
_shelx_estimated_absorpt_T_min   0.575
_shelx_estimated_absorpt_T_max   0.728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0704
_exptl_absorpt_correction_T_max  0.1094
_exptl_absorpt_process_details   
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-Ray tube'
_diffrn_source_power             50
_diffrn_source_current           30
_diffrn_source_size              '0.6 mm, fine-focus'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            95224
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_av_R_equivalents  0.0852
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.492
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             12469
_reflns_number_gt                10288
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.794
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    
'SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0217P)²+1.9705P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3865 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         12469
_refine_ls_number_parameters     621
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0754
_refine_ls_wR_factor_gt          0.0670
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Br1A Br 0.99277(6) 0.08821(2) 0.98507(2) 0.03006(10) Uani 1 1 d . . . . .
Cl1A Cl 0.56159(14) 0.14268(5) 0.78799(4) 0.0361(3) Uani 1 1 d . . . . .
O1A O 0.4965(5) 0.22058(11) 0.36753(10) 0.0377(7) Uani 1 1 d . . . . .
O2A O 0.6131(5) 0.26090(14) 0.74510(12) 0.0491(10) Uani 1 1 d . . . . .
C1A C 0.3494(5) 0.18496(18) 0.49420(14) 0.0236(9) Uani 1 1 d . . . . .
H1A H 0.235(3) 0.1734(3) 0.5112(5) 0.028 Uiso 1 1 calc R U . . .
H1B H 0.3728(8) 0.2240(11) 0.5038(3) 0.028 Uiso 1 1 calc R U . . .
C2A C 0.3263(6) 0.1811(2) 0.43605(15) 0.0267(10) Uani 1 1 d . . . . .
H2A H 0.2962(11) 0.1451(11) 0.4269(3) 0.032 Uiso 1 1 calc R U . . .
H2B H 0.232(3) 0.2042(7) 0.4256(4) 0.032 Uiso 1 1 calc R U . . .
C3A C 0.4970(7) 0.19758(14) 0.40952(13) 0.0263(8) Uani 1 1 d . . . . .
C4A C 0.6640(6) 0.18143(17) 0.43475(15) 0.0225(9) Uani 1 1 d . . . . .
H4A H 0.772(5) 0.1888(4) 0.4182(8) 0.027 Uiso 1 1 calc R U . . .
C5A C 0.6698(5) 0.15641(15) 0.48060(14) 0.0182(8) Uani 1 1 d . . . . .
C6A C 0.8433(5) 0.13331(18) 0.50074(14) 0.0246(9) Uani 1 1 d . . . . .
H6B H 0.943(3) 0.1445(3) 0.4779(7) 0.030 Uiso 1 1 calc R U . . .
H6A H 0.8366(5) 0.0929(12) 0.50026(14) 0.030 Uiso 1 1 calc R U . . .
C7A C 0.8848(5) 0.15241(17) 0.55526(14) 0.0213(8) Uani 1 1 d . . . . .
H7A H 0.987(3) 0.1342(5) 0.5674(4) 0.026 Uiso 1 1 calc R U . . .
H7B H 0.9088(9) 0.1901(11) 0.55513(14) 0.026 Uiso 1 1 calc R U . . .
C8A C 0.7260(5) 0.14061(17) 0.59065(14) 0.0180(8) Uani 1 1 d . . . . .
H8A H 0.7068(10) 0.1023(17) 0.59155(14) 0.022 Uiso 1 1 calc R U . . .
C9A C 0.5541(5) 0.16840(17) 0.56996(13) 0.0195(8) Uani 1 1 d . . . . .
H9A H 0.5839(13) 0.2076(16) 0.56692(18) 0.023 Uiso 1 1 calc R U . . .
C10A C 0.5041(5) 0.14915(14) 0.51422(12) 0.0190(7) Uani 1 1 d . . . . .
C11A C 0.3940(5) 0.1655(2) 0.60735(15) 0.0335(11) Uani 1 1 d . . . . .
H11A H 0.3473(17) 0.1292(12) 0.60724(15) 0.040 Uiso 1 1 calc R U . . .
H11B H 0.301(3) 0.1893(8) 0.5954(4) 0.040 Uiso 1 1 calc R U . . .
C12A C 0.4425(5) 0.1815(2) 0.66301(15) 0.0369(12) Uani 1 1 d . . . . .
H12B H 0.4689(10) 0.2181(13) 0.66450(16) 0.044 Uiso 1 1 calc R U . . .
H12A H 0.346(3) 0.1749(3) 0.6840(7) 0.044 Uiso 1 1 calc R U . . .
C13A C 0.6043(5) 0.14828(17) 0.68139(14) 0.0225(8) Uani 1 1 d . . . . .
C14A C 0.7616(5) 0.16051(16) 0.64506(14) 0.0169(8) Uani 1 1 d . . . . .
H14A H 0.7732(7) 0.1988(17) 0.64344(15) 0.020 Uiso 1 1 calc R U . . .
C15A C 0.9299(5) 0.13862(16) 0.67294(13) 0.0213(8) Uani 1 1 d . . . . .
H15B H 1.033(3) 0.1618(6) 0.6659(2) 0.026 Uiso 1 1 calc R U . . .
H15A H 0.9572(10) 0.1016(10) 0.6618(3) 0.026 Uiso 1 1 calc R U . . .
C16A C 0.8828(5) 0.13961(16) 0.73130(13) 0.0185(8) Uani 1 1 d . . . . .
H16A H 0.8830(5) 0.1032(15) 0.7454(6) 0.022 Uiso 1 1 calc R U . . .
C17A C 0.6924(5) 0.16467(17) 0.73290(14) 0.0204(8) Uani 1 1 d . . . . .
C18A C 0.7265(6) 0.22602(17) 0.74323(15) 0.0282(10) Uani 1 1 d . . . . .
C19A C 0.9265(6) 0.23479(16) 0.75147(15) 0.0267(9) Uani 1 1 d . . . . .
H19A H 0.9463(8) 0.2587(7) 0.7789(8) 0.032 Uiso 1 1 calc R U . . .
H19B H 0.9794(16) 0.2496(5) 0.7220(8) 0.032 Uiso 1 1 calc R U . . .
C20A C 1.0053(6) 0.17841(14) 0.76312(13) 0.0212(7) Uani 1 1 d . . . . .
H20A H 1.119(5) 0.17682(16) 0.7502(6) 0.025 Uiso 1 1 calc R U . . .
C21A C 0.4470(5) 0.08809(16) 0.51294(14) 0.0266(9) Uani 1 1 d . . . . .
H21A H 0.541(3) 0.0663(6) 0.5262(10) 0.040 Uiso 1 1 calc R U . . .
H21B H 0.423(4) 0.0776(4) 0.4789(8) 0.040 Uiso 1 1 calc R U . . .
H21C H 0.343(3) 0.0833(3) 0.5330(10) 0.040 Uiso 1 1 calc R U . . .
C22A C 0.5590(6) 0.08685(19) 0.68358(16) 0.0395(12) Uani 1 1 d . . . . .
H22A H 0.665(3) 0.0664(6) 0.6934(12) 0.059 Uiso 1 1 calc R U . . .
H22B H 0.519(4) 0.0747(5) 0.6502(9) 0.059 Uiso 1 1 calc R U . . .
H22C H 0.465(4) 0.0807(3) 0.7085(11) 0.059 Uiso 1 1 calc R U . . .
C23A C 1.0098(5) 0.16126(14) 0.81901(12) 0.0194(7) Uani 1 1 d . . . . .
C24A C 0.9112(5) 0.18691(17) 0.85765(14) 0.0214(8) Uani 1 1 d . . . . .
H24A H 0.850(3) 0.2174(15) 0.8505(4) 0.026 Uiso 1 1 calc R U . . .
C25A C 0.9064(5) 0.16573(17) 0.90732(14) 0.0226(8) Uani 1 1 d . . . . .
H25A H 0.838(3) 0.1844(8) 0.9343(12) 0.027 Uiso 1 1 calc R U . . .
C26A C 0.9994(5) 0.11813(15) 0.91780(12) 0.0216(7) Uani 1 1 d . . . . .
C27A C 1.1020(5) 0.09202(16) 0.88054(14) 0.0216(8) Uani 1 1 d . . . . .
H27A H 1.165(3) 0.0604(14) 0.8882(4) 0.026 Uiso 1 1 calc R U . . .
C28A C 1.1071(5) 0.11428(16) 0.83172(14) 0.0202(8) Uani 1 1 d . . . . .
H28A H 1.177(3) 0.0976(8) 0.8070(11) 0.024 Uiso 1 1 calc R U . . .
Br1B Br -0.02577(5) 0.20887(2) 1.11559(2) 0.02671(9) Uani 1 1 d . . . . .
Cl1B Cl -0.38653(15) 0.46363(5) 0.90344(4) 0.0327(2) Uani 1 1 d . . . . .
O1B O 0.6604(4) 0.46174(14) 0.59193(12) 0.0391(8) Uani 1 1 d . . . . .
O2B O -0.0036(6) 0.52732(11) 0.90920(10) 0.0449(9) Uani 1 1 d . . . . .
C1B C 0.2795(6) 0.50165(17) 0.67073(16) 0.0277(9) Uani 1 1 d . . . . .
H1C H 0.179(3) 0.5288(8) 0.66819(17) 0.033 Uiso 1 1 calc R U . . .
H1D H 0.362(2) 0.5139(4) 0.6987(8) 0.033 Uiso 1 1 calc R U . . .
C2B C 0.3830(6) 0.50082(18) 0.62005(17) 0.0320(10) Uani 1 1 d . . . . .
H2C H 0.301(3) 0.4940(3) 0.5927(9) 0.038 Uiso 1 1 calc R U . . .
H2D H 0.4360(17) 0.5358(11) 0.6145(3) 0.038 Uiso 1 1 calc R U . . .
C3B C 0.5276(5) 0.45791(17) 0.61944(15) 0.0300(9) Uani 1 1 d . . . . .
C4B C 0.4964(6) 0.40999(17) 0.65237(13) 0.0261(8) Uani 1 1 d . . . . .
H4B H 0.587(4) 0.3827(13) 0.65342(14) 0.031 Uiso 1 1 calc R U . . .
C5B C 0.3484(5) 0.40226(17) 0.68110(14) 0.0229(8) Uani 1 1 d . . . . .
C6B C 0.3165(5) 0.34893(16) 0.70810(15) 0.0237(9) Uani 1 1 d . . . . .
H6D H 0.426(3) 0.3279(7) 0.70766(15) 0.028 Uiso 1 1 calc R U . . .
H6C H 0.227(3) 0.3286(6) 0.6897(6) 0.028 Uiso 1 1 calc R U . . .
C7B C 0.2550(5) 0.35608(16) 0.76371(15) 0.0212(8) Uani 1 1 d . . . . .
H7C H 0.2276(9) 0.3207(10) 0.7783(5) 0.025 Uiso 1 1 calc R U . . .
H7D H 0.351(3) 0.3723(5) 0.7836(6) 0.025 Uiso 1 1 calc R U . . .
C8B C 0.0886(5) 0.39265(15) 0.76653(14) 0.0182(8) Uani 1 1 d . . . . .
H8B H -0.011(4) 0.3745(8) 0.7475(8) 0.022 Uiso 1 1 calc R U . . .
C9B C 0.1279(5) 0.44837(15) 0.74107(14) 0.0193(8) Uani 1 1 d . . . . .
H9B H 0.228(4) 0.4659(7) 0.7623(9) 0.023 Uiso 1 1 calc R U . . .
C10B C 0.2006(5) 0.44519(16) 0.68491(15) 0.0208(8) Uani 1 1 d . . . . .
C11B C -0.0344(5) 0.48738(15) 0.74521(13) 0.0212(8) Uani 1 1 d . . . . .
H11D H -0.0046(9) 0.5216(9) 0.7299(4) 0.025 Uiso 1 1 calc R U . . .
H11C H -0.133(3) 0.4723(4) 0.7269(5) 0.025 Uiso 1 1 calc R U . . .
C12B C -0.0887(5) 0.49653(16) 0.80115(14) 0.0220(8) Uani 1 1 d . . . . .
H12D H 0.008(3) 0.5133(5) 0.8191(6) 0.026 Uiso 1 1 calc R U . . .
H12C H -0.189(3) 0.5203(7) 0.80261(15) 0.026 Uiso 1 1 calc R U . . .
C13B C -0.1359(5) 0.44200(16) 0.82645(14) 0.0202(8) Uani 1 1 d . . . . .
C14B C 0.0272(5) 0.40292(13) 0.82200(12) 0.0166(7) Uani 1 1 d . . . . .
H14B H 0.134(4) 0.4221(8) 0.8405(7) 0.020 Uiso 1 1 calc R U . . .
C15B C -0.0290(5) 0.35441(14) 0.85622(13) 0.0206(8) Uani 1 1 d . . . . .
H15D H 0.068(3) 0.3336(7) 0.8650(3) 0.025 Uiso 1 1 calc R U . . .
H15C H -0.112(2) 0.3329(7) 0.8402(5) 0.025 Uiso 1 1 calc R U . . .
C16B C -0.1115(5) 0.38296(16) 0.90384(14) 0.0200(8) Uani 1 1 d . . . . .
H16B H -0.218(5) 0.3637(9) 0.9154(5) 0.024 Uiso 1 1 calc R U . . .
C17B C -0.1608(5) 0.44194(15) 0.88512(15) 0.0211(8) Uani 1 1 d . . . . .
C18B C -0.0437(6) 0.48064(16) 0.91892(15) 0.0273(9) Uani 1 1 d . . . . .
C19B C 0.0038(6) 0.44952(14) 0.96688(13) 0.0254(8) Uani 1 1 d . . . . .
H19C H -0.091(3) 0.45233(16) 0.9921(7) 0.031 Uiso 1 1 calc R U . . .
H19D H 0.114(3) 0.4633(4) 0.9817(4) 0.031 Uiso 1 1 calc R U . . .
C20B C 0.0267(5) 0.38998(14) 0.94876(13) 0.0198(8) Uani 1 1 d . . . . .
H20B H 0.150(5) 0.38687(19) 0.9335(6) 0.024 Uiso 1 1 calc R U . . .
C21B C 0.0492(5) 0.42956(17) 0.64728(14) 0.0259(9) Uani 1 1 d . . . . .
H21D H -0.014(3) 0.3969(10) 0.6601(6) 0.039 Uiso 1 1 calc R U . . .
H21E H 0.1012(13) 0.4216(11) 0.6134(8) 0.039 Uiso 1 1 calc R U . . .
H21F H -0.036(3) 0.4602(8) 0.6443(8) 0.039 Uiso 1 1 calc R U . . .
C22B C -0.3040(5) 0.41744(17) 0.80100(15) 0.0239(9) Uani 1 1 d . . . . .
H22D H -0.347(2) 0.3879(10) 0.8211(7) 0.036 Uiso 1 1 calc R U . . .
H22E H -0.2742(12) 0.4046(11) 0.7678(9) 0.036 Uiso 1 1 calc R U . . .
H22F H -0.394(3) 0.4446(7) 0.7984(9) 0.036 Uiso 1 1 calc R U . . .
C23B C 0.0116(5) 0.34624(14) 0.98989(13) 0.0207(7) Uani 1 1 d . . . . .
C24B C -0.0578(5) 0.35675(17) 1.03851(14) 0.0227(8) Uani 1 1 d . . . . .
H24B H -0.0976(18) 0.3936(16) 1.0469(4) 0.027 Uiso 1 1 calc R U . . .
C25B C -0.0715(5) 0.31586(17) 1.07532(15) 0.0234(9) Uani 1 1 d . . . . .
H25B H -0.119(2) 0.3232(4) 1.1063(15) 0.028 Uiso 1 1 calc R U . . .
C26B C -0.0121(5) 0.26406(15) 1.06386(13) 0.0213(7) Uani 1 1 d . . . . .
C27B C 0.0592(5) 0.25158(16) 1.01597(15) 0.0229(8) Uani 1 1 d . . . . .
H27B H 0.1010(18) 0.2143(16) 1.0081(4) 0.027 Uiso 1 1 calc R U . . .
C28B C 0.0701(5) 0.29297(16) 0.97958(14) 0.0220(8) Uani 1 1 d . . . . .
H28B H 0.118(2) 0.2850(4) 0.9475(14) 0.026 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Br1A C26A 1.897(3) . ?
Cl1A C17A 1.812(4) . ?
O1A C3A 1.228(4) . ?
O2A C18A 1.196(5) . ?
C1A C2A 1.526(5) . ?
C1A C10A 1.533(5) . ?
C1A H1A 1.00(3) . ?
C1A H1B 1.00(3) . ?
C2A C3A 1.497(6) . ?
C2A H2A 0.94(3) . ?
C2A H2B 0.94(3) . ?
C3A C4A 1.456(6) . ?
C4A C5A 1.341(5) . ?
C4A H4A 0.93(4) . ?
C5A C6A 1.499(5) . ?
C5A C10A 1.518(5) . ?
C6A C7A 1.524(5) . ?
C6A H6B 0.99(3) . ?
C6A H6A 0.99(3) . ?
C7A C8A 1.522(5) . ?
C7A H7A 0.94(3) . ?
C7A H7B 0.94(3) . ?
C8A C14A 1.520(5) . ?
C8A C9A 1.540(5) . ?
C8A H8A 0.94(4) . ?
C9A C11A 1.537(5) . ?
C9A C10A 1.569(5) . ?
C9A H9A 0.98(4) . ?
C10A C21A 1.547(5) . ?
C11A C12A 1.542(5) . ?
C11A H11A 0.95(3) . ?
C11A H11B 0.95(3) . ?
C12A C13A 1.524(5) . ?
C12A H12B 0.91(3) . ?
C12A H12A 0.91(3) . ?
C13A C14A 1.531(5) . ?
C13A C22A 1.534(6) . ?
C13A C17A 1.544(5) . ?
C14A C15A 1.539(5) . ?
C14A H14A 0.94(4) . ?
C15A C16A 1.559(5) . ?
C15A H15B 0.97(3) . ?
C15A H15A 0.97(3) . ?
C16A C17A 1.539(5) . ?
C16A C20A 1.550(5) . ?
C16A H16A 0.96(4) . ?
C17A C18A 1.539(6) . ?
C18A C19A 1.514(6) . ?
C19A C20A 1.523(5) . ?
C19A H19A 0.93(3) . ?
C19A H19B 0.93(3) . ?
C20A C23A 1.514(4) . ?
C20A H20A 0.91(4) . ?
C21A H21A 0.94(2) . ?
C21A H21B 0.94(2) . ?
C21A H21C 0.94(2) . ?
C22A H22A 0.97(2) . ?
C22A H22B 0.97(2) . ?
C22A H22C 0.97(2) . ?
C23A C24A 1.391(5) . ?
C23A C28A 1.393(5) . ?
C24A C25A 1.392(5) . ?
C24A H24A 0.89(4) . ?
C25A C26A 1.376(5) . ?
C25A H25A 0.98(4) . ?
C26A C27A 1.387(5) . ?
C27A C28A 1.382(5) . ?
C27A H27A 0.92(4) . ?
C28A H28A 0.92(4) . ?
Br1B C26B 1.905(3) . ?
Cl1B C17B 1.819(4) . ?
O1B C3B 1.221(5) . ?
O2B C18B 1.202(5) . ?
C1B C2B 1.526(5) . ?
C1B C10B 1.539(6) . ?
C1B H1C 1.00(3) . ?
C1B H1D 1.00(3) . ?
C2B C3B 1.497(6) . ?
C2B H2C 0.95(3) . ?
C2B H2D 0.95(3) . ?
C3B C4B 1.466(5) . ?
C4B C5B 1.341(5) . ?
C4B H4B 0.95(4) . ?
C5B C6B 1.496(6) . ?
C5B C10B 1.518(5) . ?
C6B C7B 1.527(5) . ?
C6B H6D 0.96(3) . ?
C6B H6C 0.96(3) . ?
C7B C8B 1.523(5) . ?
C7B H7C 0.96(3) . ?
C7B H7D 0.96(3) . ?
C8B C14B 1.534(5) . ?
C8B C9B 1.538(5) . ?
C8B H8B 1.00(4) . ?
C9B C11B 1.537(5) . ?
C9B C10B 1.560(5) . ?
C9B H9B 1.02(4) . ?
C10B C21B 1.538(5) . ?
C11B C12B 1.527(5) . ?
C11B H11D 0.95(3) . ?
C11B H11C 0.95(3) . ?
C12B C13B 1.523(5) . ?
C12B H12D 0.95(3) . ?
C12B H12C 0.95(3) . ?
C13B C22B 1.533(5) . ?
C13B C17B 1.538(5) . ?
C13B C14B 1.544(5) . ?
C14B C15B 1.537(5) . ?
C14B H14B 1.04(4) . ?
C15B C16B 1.547(5) . ?
C15B H15D 0.91(3) . ?
C15B H15C 0.91(3) . ?
C16B C17B 1.560(5) . ?
C16B C20B 1.564(5) . ?
C16B H16B 0.97(4) . ?
C17B C18B 1.554(6) . ?
C18B C19B 1.502(5) . ?
C19B C20B 1.534(5) . ?
C19B H19C 0.97(3) . ?
C19B H19D 0.97(3) . ?
C20B C23B 1.514(5) . ?
C20B H20B 1.00(4) . ?
C21B H21D 0.98(2) . ?
C21B H21E 0.98(2) . ?
C21B H21F 0.98(2) . ?
C22B H22D 0.94(2) . ?
C22B H22E 0.94(2) . ?
C22B H22F 0.94(2) . ?
C23B C24B 1.390(5) . ?
C23B C28B 1.394(5) . ?
C24B C25B 1.386(5) . ?
C24B H24B 0.97(4) . ?
C25B C26B 1.369(5) . ?
C25B H25B 0.90(4) . ?
C26B C27B 1.387(5) . ?
C27B C28B 1.386(5) . ?
C27B H27B 0.98(4) . ?
C28B H28B 0.93(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
C2A C1A C10A 112.7(3) . . ?
C2A C1A H1A 109.0 . . ?
C10A C1A H1A 109.0 . . ?
C2A C1A H1B 109.0 . . ?
C10A C1A H1B 109.0 . . ?
H1A C1A H1B 107.8 . . ?
C3A C2A C1A 110.2(3) . . ?
C3A C2A H2A 109.6 . . ?
C1A C2A H2A 109.6 . . ?
C3A C2A H2B 109.6 . . ?
C1A C2A H2B 109.6 . . ?
H2A C2A H2B 108.1 . . ?
O1A C3A C4A 121.8(4) . . ?
O1A C3A C2A 122.0(4) . . ?
C4A C3A C2A 116.1(3) . . ?
C5A C4A C3A 123.4(4) . . ?
C5A C4A H4A 118.3 . . ?
C3A C4A H4A 118.3 . . ?
C4A C5A C6A 120.6(4) . . ?
C4A C5A C10A 122.7(3) . . ?
C6A C5A C10A 116.7(3) . . ?
C5A C6A C7A 112.6(3) . . ?
C5A C6A H6B 109.1 . . ?
C7A C6A H6B 109.1 . . ?
C5A C6A H6A 109.1 . . ?
C7A C6A H6A 109.1 . . ?
H6B C6A H6A 107.8 . . ?
C8A C7A C6A 110.4(3) . . ?
C8A C7A H7A 109.6 . . ?
C6A C7A H7A 109.6 . . ?
C8A C7A H7B 109.6 . . ?
C6A C7A H7B 109.6 . . ?
H7A C7A H7B 108.1 . . ?
C14A C8A C7A 111.7(3) . . ?
C14A C8A C9A 109.2(3) . . ?
C7A C8A C9A 110.2(3) . . ?
C14A C8A H8A 108.6 . . ?
C7A C8A H8A 108.6 . . ?
C9A C8A H8A 108.6 . . ?
C11A C9A C8A 113.4(3) . . ?
C11A C9A C10A 112.9(3) . . ?
C8A C9A C10A 112.8(3) . . ?
C11A C9A H9A 105.6 . . ?
C8A C9A H9A 105.6 . . ?
C10A C9A H9A 105.6 . . ?
C5A C10A C1A 110.1(3) . . ?
C5A C10A C21A 108.7(3) . . ?
C1A C10A C21A 109.6(3) . . ?
C5A C10A C9A 107.9(3) . . ?
C1A C10A C9A 108.7(3) . . ?
C21A C10A C9A 111.8(3) . . ?
C9A C11A C12A 113.8(3) . . ?
C9A C11A H11A 108.8 . . ?
C12A C11A H11A 108.8 . . ?
C9A C11A H11B 108.8 . . ?
C12A C11A H11B 108.8 . . ?
H11A C11A H11B 107.7 . . ?
C13A C12A C11A 110.2(4) . . ?
C13A C12A H12B 109.6 . . ?
C11A C12A H12B 109.6 . . ?
C13A C12A H12A 109.6 . . ?
C11A C12A H12A 109.6 . . ?
H12B C12A H12A 108.1 . . ?
C12A C13A C14A 107.6(3) . . ?
C12A C13A C22A 110.9(4) . . ?
C14A C13A C22A 112.3(3) . . ?
C12A C13A C17A 118.0(3) . . ?
C14A C13A C17A 99.4(3) . . ?
C22A C13A C17A 108.2(3) . . ?
C8A C14A C13A 112.4(3) . . ?
C8A C14A C15A 118.0(3) . . ?
C13A C14A C15A 105.0(3) . . ?
C8A C14A H14A 106.9 . . ?
C13A C14A H14A 106.9 . . ?
C15A C14A H14A 106.9 . . ?
C14A C15A C16A 105.8(3) . . ?
C14A C15A H15B 110.6 . . ?
C16A C15A H15B 110.6 . . ?
C14A C15A H15A 110.6 . . ?
C16A C15A H15A 110.6 . . ?
H15B C15A H15A 108.7 . . ?
C17A C16A C20A 106.3(3) . . ?
C17A C16A C15A 103.8(3) . . ?
C20A C16A C15A 113.5(3) . . ?
C17A C16A H16A 111.0 . . ?
C20A C16A H16A 111.0 . . ?
C15A C16A H16A 111.0 . . ?
C16A C17A C18A 103.8(3) . . ?
C16A C17A C13A 105.2(3) . . ?
C18A C17A C13A 118.2(3) . . ?
C16A C17A Cl1A 113.3(3) . . ?
C18A C17A Cl1A 103.7(3) . . ?
C13A C17A Cl1A 112.6(3) . . ?
O2A C18A C19A 125.6(4) . . ?
O2A C18A C17A 125.5(4) . . ?
C19A C18A C17A 108.8(3) . . ?
C18A C19A C20A 106.1(3) . . ?
C18A C19A H19A 110.5 . . ?
C20A C19A H19A 110.5 . . ?
C18A C19A H19B 110.5 . . ?
C20A C19A H19B 110.5 . . ?
H19A C19A H19B 108.7 . . ?
C23A C20A C19A 116.7(3) . . ?
C23A C20A C16A 111.0(3) . . ?
C19A C20A C16A 102.6(3) . . ?
C23A C20A H20A 108.8 . . ?
C19A C20A H20A 108.8 . . ?
C16A C20A H20A 108.8 . . ?
C10A C21A H21A 109.5 . . ?
C10A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
C10A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C13A C22A H22A 109.5 . . ?
C13A C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C13A C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
C24A C23A C28A 118.0(3) . . ?
C24A C23A C20A 124.0(3) . . ?
C28A C23A C20A 117.8(3) . . ?
C23A C24A C25A 121.2(4) . . ?
C23A C24A H24A 119.4 . . ?
C25A C24A H24A 119.4 . . ?
C26A C25A C24A 118.9(4) . . ?
C26A C25A H25A 120.6 . . ?
C24A C25A H25A 120.6 . . ?
C25A C26A C27A 121.5(3) . . ?
C25A C26A Br1A 119.6(3) . . ?
C27A C26A Br1A 118.9(3) . . ?
C28A C27A C26A 118.6(4) . . ?
C28A C27A H27A 120.7 . . ?
C26A C27A H27A 120.7 . . ?
C27A C28A C23A 121.8(4) . . ?
C27A C28A H28A 119.1 . . ?
C23A C28A H28A 119.1 . . ?
C2B C1B C10B 112.7(3) . . ?
C2B C1B H1C 109.0 . . ?
C10B C1B H1C 109.0 . . ?
C2B C1B H1D 109.0 . . ?
C10B C1B H1D 109.0 . . ?
H1C C1B H1D 107.8 . . ?
C3B C2B C1B 112.2(4) . . ?
C3B C2B H2C 109.2 . . ?
C1B C2B H2C 109.2 . . ?
C3B C2B H2D 109.2 . . ?
C1B C2B H2D 109.2 . . ?
H2C C2B H2D 107.9 . . ?
O1B C3B C4B 122.1(4) . . ?
O1B C3B C2B 122.0(4) . . ?
C4B C3B C2B 115.9(3) . . ?
C5B C4B C3B 124.5(4) . . ?
C5B C4B H4B 117.7 . . ?
C3B C4B H4B 117.7 . . ?
C4B C5B C6B 120.9(4) . . ?
C4B C5B C10B 122.0(4) . . ?
C6B C5B C10B 116.9(3) . . ?
C5B C6B C7B 113.2(3) . . ?
C5B C6B H6D 108.9 . . ?
C7B C6B H6D 108.9 . . ?
C5B C6B H6C 108.9 . . ?
C7B C6B H6C 108.9 . . ?
H6D C6B H6C 107.8 . . ?
C8B C7B C6B 110.7(3) . . ?
C8B C7B H7C 109.5 . . ?
C6B C7B H7C 109.5 . . ?
C8B C7B H7D 109.5 . . ?
C6B C7B H7D 109.5 . . ?
H7C C7B H7D 108.1 . . ?
C7B C8B C14B 112.4(3) . . ?
C7B C8B C9B 110.0(3) . . ?
C14B C8B C9B 108.5(3) . . ?
C7B C8B H8B 108.6 . . ?
C14B C8B H8B 108.6 . . ?
C9B C8B H8B 108.6 . . ?
C11B C9B C8B 111.6(3) . . ?
C11B C9B C10B 111.5(3) . . ?
C8B C9B C10B 115.2(3) . . ?
C11B C9B H9B 105.9 . . ?
C8B C9B H9B 105.9 . . ?
C10B C9B H9B 105.9 . . ?
C5B C10B C21B 108.4(3) . . ?
C5B C10B C1B 109.0(3) . . ?
C21B C10B C1B 110.2(3) . . ?
C5B C10B C9B 110.2(3) . . ?
C21B C10B C9B 110.9(3) . . ?
C1B C10B C9B 108.2(3) . . ?
C12B C11B C9B 111.3(3) . . ?
C12B C11B H11D 109.4 . . ?
C9B C11B H11D 109.4 . . ?
C12B C11B H11C 109.4 . . ?
C9B C11B H11C 109.4 . . ?
H11D C11B H11C 108.0 . . ?
C13B C12B C11B 110.2(3) . . ?
C13B C12B H12D 109.6 . . ?
C11B C12B H12D 109.6 . . ?
C13B C12B H12C 109.6 . . ?
C11B C12B H12C 109.6 . . ?
H12D C12B H12C 108.1 . . ?
C12B C13B C22B 109.9(3) . . ?
C12B C13B C17B 117.2(3) . . ?
C22B C13B C17B 109.3(3) . . ?
C12B C13B C14B 109.0(3) . . ?
C22B C13B C14B 111.4(3) . . ?
C17B C13B C14B 99.7(3) . . ?
C8B C14B C15B 120.0(3) . . ?
C8B C14B C13B 113.8(3) . . ?
C15B C14B C13B 102.6(3) . . ?
C8B C14B H14B 106.5 . . ?
C15B C14B H14B 106.5 . . ?
C13B C14B H14B 106.5 . . ?
C14B C15B C16B 103.1(3) . . ?
C14B C15B H15D 111.2 . . ?
C16B C15B H15D 111.2 . . ?
C14B C15B H15C 111.2 . . ?
C16B C15B H15C 111.2 . . ?
H15D C15B H15C 109.1 . . ?
C15B C16B C17B 104.8(3) . . ?
C15B C16B C20B 112.9(3) . . ?
C17B C16B C20B 106.6(3) . . ?
C15B C16B H16B 110.8 . . ?
C17B C16B H16B 110.8 . . ?
C20B C16B H16B 110.8 . . ?
C13B C17B C18B 119.6(3) . . ?
C13B C17B C16B 106.4(3) . . ?
C18B C17B C16B 104.5(3) . . ?
C13B C17B Cl1B 111.7(3) . . ?
C18B C17B Cl1B 100.9(3) . . ?
C16B C17B Cl1B 113.7(3) . . ?
O2B C18B C19B 126.4(4) . . ?
O2B C18B C17B 126.3(4) . . ?
C19B C18B C17B 107.2(3) . . ?
C18B C19B C20B 104.3(3) . . ?
C18B C19B H19C 110.9 . . ?
C20B C19B H19C 110.9 . . ?
C18B C19B H19D 110.9 . . ?
C20B C19B H19D 110.9 . . ?
H19C C19B H19D 108.9 . . ?
C23B C20B C19B 116.1(3) . . ?
C23B C20B C16B 113.7(3) . . ?
C19B C20B C16B 105.1(3) . . ?
C23B C20B H20B 107.1 . . ?
C19B C20B H20B 107.1 . . ?
C16B C20B H20B 107.1 . . ?
C10B C21B H21D 109.5 . . ?
C10B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
C10B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
C13B C22B H22D 109.5 . . ?
C13B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C13B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
C24B C23B C28B 117.5(3) . . ?
C24B C23B C20B 122.8(3) . . ?
C28B C23B C20B 119.7(3) . . ?
C25B C24B C23B 121.6(4) . . ?
C25B C24B H24B 119.2 . . ?
C23B C24B H24B 119.2 . . ?
C26B C25B C24B 119.2(4) . . ?
C26B C25B H25B 120.4 . . ?
C24B C25B H25B 120.4 . . ?
C25B C26B C27B 121.3(3) . . ?
C25B C26B Br1B 118.6(3) . . ?
C27B C26B Br1B 120.0(3) . . ?
C28B C27B C26B 118.5(4) . . ?
C28B C27B H27B 120.8 . . ?
C26B C27B H27B 120.8 . . ?
C27B C28B C23B 121.8(3) . . ?
C27B C28B H28B 119.1 . . ?
C23B C28B H28B 119.1 . . ?

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
C10A C1A C2A C3A -58.0(5) . . . . ?
C1A C2A C3A O1A -147.6(4) . . . . ?
C1A C2A C3A C4A 36.4(4) . . . . ?
O1A C3A C4A C5A 179.8(4) . . . . ?
C2A C3A C4A C5A -4.2(5) . . . . ?
C3A C4A C5A C6A 170.7(4) . . . . ?
C3A C4A C5A C10A -8.4(6) . . . . ?
C4A C5A C6A C7A 129.0(4) . . . . ?
C10A C5A C6A C7A -51.8(5) . . . . ?
C5A C6A C7A C8A 53.4(5) . . . . ?
C6A C7A C8A C14A -178.6(3) . . . . ?
C6A C7A C8A C9A -57.0(4) . . . . ?
C14A C8A C9A C11A -48.7(4) . . . . ?
C7A C8A C9A C11A -171.7(3) . . . . ?
C14A C8A C9A C10A -178.6(3) . . . . ?
C7A C8A C9A C10A 58.3(4) . . . . ?
C4A C5A C10A C1A -12.8(5) . . . . ?
C6A C5A C10A C1A 168.0(3) . . . . ?
C4A C5A C10A C21A 107.2(4) . . . . ?
C6A C5A C10A C21A -71.9(4) . . . . ?
C4A C5A C10A C9A -131.3(4) . . . . ?
C6A C5A C10A C9A 49.5(4) . . . . ?
C2A C1A C10A C5A 45.6(5) . . . . ?
C2A C1A C10A C21A -74.0(4) . . . . ?
C2A C1A C10A C9A 163.6(3) . . . . ?
C11A C9A C10A C5A 177.4(3) . . . . ?
C8A C9A C10A C5A -52.4(4) . . . . ?
C11A C9A C10A C1A 58.0(4) . . . . ?
C8A C9A C10A C1A -171.7(3) . . . . ?
C11A C9A C10A C21A -63.1(4) . . . . ?
C8A C9A C10A C21A 67.1(4) . . . . ?
C8A C9A C11A C12A 47.2(5) . . . . ?
C10A C9A C11A C12A 177.1(4) . . . . ?
C9A C11A C12A C13A -52.4(5) . . . . ?
C11A C12A C13A C14A 59.2(5) . . . . ?
C11A C12A C13A C22A -64.0(4) . . . . ?
C11A C12A C13A C17A 170.5(4) . . . . ?
C7A C8A C14A C13A -179.2(3) . . . . ?
C9A C8A C14A C13A 58.6(4) . . . . ?
C7A C8A C14A C15A -56.7(5) . . . . ?
C9A C8A C14A C15A -178.9(3) . . . . ?
C12A C13A C14A C8A -64.8(4) . . . . ?
C22A C13A C14A C8A 57.6(4) . . . . ?
C17A C13A C14A C8A 171.8(3) . . . . ?
C12A C13A C14A C15A 165.7(3) . . . . ?
C22A C13A C14A C15A -72.0(4) . . . . ?
C17A C13A C14A C15A 42.2(4) . . . . ?
C8A C14A C15A C16A -151.4(3) . . . . ?
C13A C14A C15A C16A -25.3(4) . . . . ?
C14A C15A C16A C17A -2.5(4) . . . . ?
C14A C15A C16A C20A -117.5(3) . . . . ?
C20A C16A C17A C18A 24.4(4) . . . . ?
C15A C16A C17A C18A -95.6(3) . . . . ?
C20A C16A C17A C13A 149.2(3) . . . . ?
C15A C16A C17A C13A 29.3(4) . . . . ?
C20A C16A C17A Cl1A -87.4(3) . . . . ?
C15A C16A C17A Cl1A 152.6(3) . . . . ?
C12A C13A C17A C16A -160.1(3) . . . . ?
C14A C13A C17A C16A -44.3(4) . . . . ?
C22A C13A C17A C16A 73.1(4) . . . . ?
C12A C13A C17A C18A -44.8(5) . . . . ?
C14A C13A C17A C18A 71.0(4) . . . . ?
C22A C13A C17A C18A -171.7(4) . . . . ?
C12A C13A C17A Cl1A 76.1(4) . . . . ?
C14A C13A C17A Cl1A -168.1(3) . . . . ?
C22A C13A C17A Cl1A -50.8(4) . . . . ?
C16A C17A C18A O2A 176.5(4) . . . . ?
C13A C17A C18A O2A 60.5(6) . . . . ?
Cl1A C17A C18A O2A -64.8(5) . . . . ?
C16A C17A C18A C19A -4.4(4) . . . . ?
C13A C17A C18A C19A -120.4(4) . . . . ?
Cl1A C17A C18A C19A 114.2(3) . . . . ?
O2A C18A C19A C20A 161.5(4) . . . . ?
C17A C18A C19A C20A -17.6(4) . . . . ?
C18A C19A C20A C23A -89.6(4) . . . . ?
C18A C19A C20A C16A 31.9(4) . . . . ?
C17A C16A C20A C23A 90.2(4) . . . . ?
C15A C16A C20A C23A -156.4(3) . . . . ?
C17A C16A C20A C19A -35.1(4) . . . . ?
C15A C16A C20A C19A 78.3(4) . . . . ?
C19A C20A C23A C24A 15.7(6) . . . . ?
C16A C20A C23A C24A -101.3(4) . . . . ?
C19A C20A C23A C28A -169.7(3) . . . . ?
C16A C20A C23A C28A 73.3(4) . . . . ?
C28A C23A C24A C25A -1.4(6) . . . . ?
C20A C23A C24A C25A 173.2(4) . . . . ?
C23A C24A C25A C26A -0.8(6) . . . . ?
C24A C25A C26A C27A 2.1(6) . . . . ?
C24A C25A C26A Br1A -179.4(3) . . . . ?
C25A C26A C27A C28A -1.1(6) . . . . ?
Br1A C26A C27A C28A -179.6(3) . . . . ?
C26A C27A C28A C23A -1.2(6) . . . . ?
C24A C23A C28A C27A 2.5(6) . . . . ?
C20A C23A C28A C27A -172.5(3) . . . . ?
C10B C1B C2B C3B -54.5(5) . . . . ?
C1B C2B C3B O1B -154.9(4) . . . . ?
C1B C2B C3B C4B 27.4(5) . . . . ?
O1B C3B C4B C5B -176.1(4) . . . . ?
C2B C3B C4B C5B 1.5(6) . . . . ?
C3B C4B C5B C6B 171.8(4) . . . . ?
C3B C4B C5B C10B -4.0(6) . . . . ?
C4B C5B C6B C7B 134.7(4) . . . . ?
C10B C5B C6B C7B -49.3(5) . . . . ?
C5B C6B C7B C8B 54.8(4) . . . . ?
C6B C7B C8B C14B -177.5(3) . . . . ?
C6B C7B C8B C9B -56.5(4) . . . . ?
C7B C8B C9B C11B -177.6(3) . . . . ?
C14B C8B C9B C11B -54.2(4) . . . . ?
C7B C8B C9B C10B 54.0(4) . . . . ?
C14B C8B C9B C10B 177.3(3) . . . . ?
C4B C5B C10B C21B 97.9(4) . . . . ?
C6B C5B C10B C21B -78.1(4) . . . . ?
C4B C5B C10B C1B -22.1(5) . . . . ?
C6B C5B C10B C1B 161.9(3) . . . . ?
C4B C5B C10B C9B -140.7(4) . . . . ?
C6B C5B C10B C9B 43.4(4) . . . . ?
C2B C1B C10B C5B 50.5(5) . . . . ?
C2B C1B C10B C21B -68.3(4) . . . . ?
C2B C1B C10B C9B 170.3(3) . . . . ?
C11B C9B C10B C5B -174.5(3) . . . . ?
C8B C9B C10B C5B -46.0(4) . . . . ?
C11B C9B C10B C21B -54.5(4) . . . . ?
C8B C9B C10B C21B 74.0(4) . . . . ?
C11B C9B C10B C1B 66.5(4) . . . . ?
C8B C9B C10B C1B -165.1(3) . . . . ?
C8B C9B C11B C12B 57.5(4) . . . . ?
C10B C9B C11B C12B -172.1(3) . . . . ?
C9B C11B C12B C13B -58.7(4) . . . . ?
C11B C12B C13B C22B -65.0(4) . . . . ?
C11B C12B C13B C17B 169.3(3) . . . . ?
C11B C12B C13B C14B 57.2(4) . . . . ?
C7B C8B C14B C15B -60.7(4) . . . . ?
C9B C8B C14B C15B 177.5(3) . . . . ?
C7B C8B C14B C13B 177.3(3) . . . . ?
C9B C8B C14B C13B 55.5(4) . . . . ?
C12B C13B C14B C8B -57.6(4) . . . . ?
C22B C13B C14B C8B 63.8(4) . . . . ?
C17B C13B C14B C8B 179.1(3) . . . . ?
C12B C13B C14B C15B 171.2(3) . . . . ?
C22B C13B C14B C15B -67.4(4) . . . . ?
C17B C13B C14B C15B 47.9(3) . . . . ?
C8B C14B C15B C16B -170.3(3) . . . . ?
C13B C14B C15B C16B -42.9(3) . . . . ?
C14B C15B C16B C17B 20.4(4) . . . . ?
C14B C15B C16B C20B -95.3(3) . . . . ?
C12B C13B C17B C18B -34.3(5) . . . . ?
C22B C13B C17B C18B -160.2(3) . . . . ?
C14B C13B C17B C18B 83.0(4) . . . . ?
C12B C13B C17B C16B -152.2(3) . . . . ?
C22B C13B C17B C16B 81.9(4) . . . . ?
C14B C13B C17B C16B -34.9(4) . . . . ?
C12B C13B C17B Cl1B 83.2(4) . . . . ?
C22B C13B C17B Cl1B -42.7(4) . . . . ?
C14B C13B C17B Cl1B -159.5(2) . . . . ?
C15B C16B C17B C13B 9.4(4) . . . . ?
C20B C16B C17B C13B 129.3(3) . . . . ?
C15B C16B C17B C18B -118.1(3) . . . . ?
C20B C16B C17B C18B 1.8(4) . . . . ?
C15B C16B C17B Cl1B 132.8(3) . . . . ?
C20B C16B C17B Cl1B -107.3(3) . . . . ?
C13B C17B C18B O2B 40.5(6) . . . . ?
C16B C17B C18B O2B 159.4(4) . . . . ?
Cl1B C17B C18B O2B -82.4(5) . . . . ?
C13B C17B C18B C19B -141.6(4) . . . . ?
C16B C17B C18B C19B -22.7(4) . . . . ?
Cl1B C17B C18B C19B 95.4(3) . . . . ?
O2B C18B C19B C20B -147.2(5) . . . . ?
C17B C18B C19B C20B 35.0(4) . . . . ?
C18B C19B C20B C23B -159.7(3) . . . . ?
C18B C19B C20B C16B -33.0(4) . . . . ?
C15B C16B C20B C23B -98.4(4) . . . . ?
C17B C16B C20B C23B 147.0(3) . . . . ?
C15B C16B C20B C19B 133.6(3) . . . . ?
C17B C16B C20B C19B 19.0(4) . . . . ?
C19B C20B C23B C24B 14.0(6) . . . . ?
C16B C20B C23B C24B -108.2(4) . . . . ?
C19B C20B C23B C28B -165.5(4) . . . . ?
C16B C20B C23B C28B 72.3(5) . . . . ?
C28B C23B C24B C25B -1.0(6) . . . . ?
C20B C23B C24B C25B 179.5(4) . . . . ?
C23B C24B C25B C26B 1.2(6) . . . . ?
C24B C25B C26B C27B -0.8(6) . . . . ?
C24B C25B C26B Br1B 178.3(3) . . . . ?
C25B C26B C27B C28B 0.3(6) . . . . ?
Br1B C26B C27B C28B -178.8(3) . . . . ?
C26B C27B C28B C23B 0.0(6) . . . . ?
C24B C23B C28B C27B 0.4(6) . . . . ?
C20B C23B C28B C27B 179.9(4) . . . . ?

_refine_diff_density_max         0.360
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.071



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3e
_database_code_depnum_ccdc_archive 'CCDC 2060482'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-04-27 deposited with the CCDC.	2022-02-02 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT911_3e                  
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report  
RESPONSE: Six reflections 2 0 0, 1 2 0, 1 3 0, 1 2 1, 0 0 2 and 1 0 7
were behind the beamstop. 
;
_vrf_PLAT910_3e                  
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).          1 Note 
RESPONSE: Reflections 0 1 1 was behind the beamstop. 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H32 Cl F O2'
_chemical_formula_sum            'C28 H32 Cl F O2'
_chemical_formula_weight         454.98

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.6037(2)
_cell_length_b                   14.6224(4)
_cell_length_c                   16.3071(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2289.99(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9858
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      36.10

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.34
_exptl_absorpt_coefficient_mu    0.199
_shelx_estimated_absorpt_T_min   0.899
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7143
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10).'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-Ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            103490
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.461
_diffrn_reflns_theta_max         36.365
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             11117
_reflns_number_gt                10073
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    
;
SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)
;
_computing_structure_refinement  
;
SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)
;
_computing_molecular_graphics    
;
SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)
;
_computing_publication_material  
;
SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0617P)²+0.1438P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 4150 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.042(18)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         11117
_refine_ls_number_parameters     318
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1084
_refine_ls_wR_factor_gt          0.1030
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Cl1A Cl 0.78569(7) 0.56268(5) 0.83220(4) 0.03820(16) Uani 0.7248(19) 1 d D . P
A 1
F1A F 0.4255(2) 0.68811(14) 1.03041(13) 0.0345(3) Uani 0.7248(19) 1 d D . P A 1
Cl1B Cl 0.4042(2) 0.71248(14) 1.04062(13) 0.0345(3) Uani 0.2752(19) 1 d D . P A
2
F1B F 0.7718(5) 0.5606(4) 0.8572(2) 0.03820(16) Uani 0.2752(19) 1 d D . P A 2
O1 O 0.36585(15) 0.61779(9) 0.23147(7) 0.0411(3) Uani 1 1 d . . . . .
O2 O 0.41492(12) 0.89472(6) 0.78750(7) 0.0304(2) Uani 1 1 d . . . . .
C1 C 0.22244(14) 0.73099(9) 0.41055(8) 0.0260(2) Uani 1 1 d . . . . .
H1A H 0.1443(12) 0.7726(7) 0.42157(19) 0.031 Uiso 1 1 calc R U . . .
H1B H 0.3091(14) 0.7653(5) 0.41932(16) 0.031 Uiso 1 1 calc R U . . .
C2 C 0.21582(17) 0.70051(10) 0.32126(9) 0.0320(3) Uani 1 1 d . . . . .
H2A H 0.1266(15) 0.6763(4) 0.3103(2) 0.038 Uiso 1 1 calc R U . . .
H2B H 0.2289(3) 0.7518(9) 0.2870(6) 0.038 Uiso 1 1 calc R U . . .
C3 C 0.32378(16) 0.62970(10) 0.30133(8) 0.0297(3) Uani 1 1 d . . . . .
C4 C 0.36970(14) 0.57081(9) 0.36880(8) 0.0259(2) Uani 1 1 d . . . . .
H4 H 0.4427(17) 0.5255(10) 0.3578(3) 0.031 Uiso 1 1 calc R U . . .
C5 C 0.31650(12) 0.57577(8) 0.44532(7) 0.02132(19) Uani 1 1 d . . . . .
C6 C 0.34972(13) 0.50284(8) 0.50733(8) 0.0234(2) Uani 1 1 d . . . . .
H6B H 0.4257(11) 0.4620(6) 0.4850(3) 0.028 Uiso 1 1 calc R U . . .
H6A H 0.2643(13) 0.4638(6) 0.51669(16) 0.028 Uiso 1 1 calc R U . . .
C7 C 0.39703(13) 0.54355(8) 0.58904(7) 0.02183(19) Uani 1 1 d . . . . .
H7A H 0.4106(2) 0.4957(7) 0.6279(6) 0.026 Uiso 1 1 calc R U . . .
H7B H 0.4837(13) 0.5743(4) 0.58171(13) 0.026 Uiso 1 1 calc R U . . .
C8 C 0.28892(11) 0.61072(7) 0.62175(7) 0.01904(17) Uani 1 1 d . . . . .
H8 H 0.2030(18) 0.5784(7) 0.6315(2) 0.023 Uiso 1 1 calc R U . . .
C9 C 0.26239(11) 0.68710(7) 0.55809(7) 0.01960(17) Uani 1 1 d . . . . .
H9 H 0.3515(18) 0.7166(6) 0.54969(18) 0.024 Uiso 1 1 calc R U . . .
C10 C 0.21673(12) 0.65095(8) 0.47189(7) 0.02116(18) Uani 1 1 d . . . . .
C11 C 0.16499(14) 0.76188(9) 0.59170(9) 0.0264(2) Uani 1 1 d . . . . .
H11B H 0.15830(18) 0.8116(8) 0.5513(6) 0.032 Uiso 1 1 calc R U . . .
H11A H 0.0714(14) 0.7361(4) 0.59905(14) 0.032 Uiso 1 1 calc R U . . .
C12 C 0.21546(13) 0.80132(8) 0.67381(8) 0.0243(2) Uani 1 1 d . . . . .
H12B H 0.3009(13) 0.8318(5) 0.66602(14) 0.029 Uiso 1 1 calc R U . . .
H12A H 0.1501(10) 0.8441(7) 0.6934(3) 0.029 Uiso 1 1 calc R U . . .
C13 C 0.23408(12) 0.72491(8) 0.73693(7) 0.02140(19) Uani 1 1 d . . . . .
C14 C 0.33735(11) 0.65423(7) 0.70177(7) 0.01857(17) Uani 1 1 d . . . . .
H14 H 0.4263(17) 0.6883(7) 0.6891(3) 0.022 Uiso 1 1 calc R U . . .
C15 C 0.36865(13) 0.59128(7) 0.77446(7) 0.02089(18) Uani 1 1 d . . . . .
H15B H 0.4558(13) 0.5591(5) 0.76666(13) 0.025 Uiso 1 1 calc R U . . .
H15A H 0.2948(11) 0.5471(6) 0.78234(13) 0.025 Uiso 1 1 calc R U . . .
C16 C 0.37768(13) 0.65816(8) 0.84783(7) 0.02116(18) Uani 1 1 d . . . . .
H16 H 0.3294(9) 0.6316(5) 0.8978(10) 0.025 Uiso 1 1 calc R U . . .
C17 C 0.30482(13) 0.74831(8) 0.81966(8) 0.02228(19) Uani 1 1 d . . . . .
H17 H 0.2308(15) 0.7643(3) 0.8605(8) 0.027 Uiso 1 1 calc R U . . .
C18 C 0.41752(14) 0.82157(8) 0.82242(8) 0.0238(2) Uani 1 1 d . . . . .
C19 C 0.53302(16) 0.78966(9) 0.87845(9) 0.0286(2) Uani 1 1 d . . . . .
H19A H 0.5149(3) 0.8069(3) 0.9342(9) 0.034 Uiso 1 1 calc R U . . .
H19B H 0.6211(14) 0.8146(4) 0.8619(3) 0.034 Uiso 1 1 calc R U . . .
C20 C 0.53109(13) 0.68512(8) 0.86846(7) 0.02237(19) Uani 1 1 d . . . . .
H20 H 0.5867(12) 0.6710(3) 0.8203(10) 0.027 Uiso 1 1 calc R U . . .
C21 C 0.06850(13) 0.60982(9) 0.47352(9) 0.0274(2) Uani 1 1 d . . . . .
H21A H 0.0632(4) 0.5622(10) 0.5166(8) 0.041 Uiso 1 1 calc R U . . .
H21B H 0.0472(6) 0.5822(9) 0.4195(8) 0.041 Uiso 1 1 calc R U . . .
H21C H 0.0001(10) 0.6587(7) 0.4855(9) 0.041 Uiso 1 1 calc R U . . .
C22 C 0.09159(14) 0.68258(10) 0.75875(10) 0.0301(3) Uani 1 1 d . . . . .
H22A H 0.1037(3) 0.6375(10) 0.8017(9) 0.045 Uiso 1 1 calc R U . . .
H22B H 0.0525(9) 0.6535(9) 0.7106(7) 0.045 Uiso 1 1 calc R U . . .
H22C H 0.0292(10) 0.7302(7) 0.7776(9) 0.045 Uiso 1 1 calc R U . . .
C23 C 0.59216(13) 0.63158(8) 0.93865(8) 0.0236(2) Uani 1 1 d . . . . .
C24 C 0.53780(15) 0.63480(9) 1.01783(8) 0.0280(2) Uani 1 1 d D . . . .
C25 C 0.5885(2) 0.58465(11) 1.08347(9) 0.0365(3) Uani 1 1 d . . . . .
H25 H 0.5465(11) 0.58960(17) 1.1372(14) 0.044 Uiso 1 1 calc R U . . .
C26 C 0.7014(2) 0.52698(11) 1.06993(11) 0.0405(4) Uani 1 1 d . . . . .
H26 H 0.7390(10) 0.4911(10) 1.1148(12) 0.049 Uiso 1 1 calc R U . . .
C27 C 0.76013(17) 0.52069(11) 0.99286(12) 0.0385(3) Uani 1 1 d . . . . .
H27 H 0.839(2) 0.4804(11) 0.9834(3) 0.046 Uiso 1 1 calc R U . . .
C28 C 0.70583(14) 0.57250(9) 0.92899(9) 0.0290(2) Uani 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Cl1A C28 1.7607(14) . ?
F1A C24 1.347(2) . ?
Cl1B C24 1.753(2) . ?
F1B C28 1.342(3) . ?
O1 C3 1.2213(19) . ?
O2 C18 1.2120(15) . ?
C1 C2 1.524(2) . ?
C1 C10 1.5406(16) . ?
C1 H1A 0.983(15) . ?
C1 H1B 0.983(15) . ?
C2 C3 1.501(2) . ?
C2 H2A 0.944(16) . ?
C2 H2B 0.944(16) . ?
C3 C4 1.4651(19) . ?
C4 C5 1.3504(17) . ?
C4 H4 0.98(2) . ?
C5 C6 1.5040(16) . ?
C5 C10 1.5213(17) . ?
C6 C7 1.5285(16) . ?
C6 H6B 1.011(15) . ?
C6 H6A 1.011(15) . ?
C7 C8 1.5255(16) . ?
C7 H7A 0.953(14) . ?
C7 H7B 0.953(14) . ?
C8 C14 1.5244(15) . ?
C8 C9 1.5459(15) . ?
C8 H8 0.96(2) . ?
C9 C11 1.5398(17) . ?
C9 C10 1.5644(16) . ?
C9 H9 0.97(2) . ?
C10 C21 1.5456(17) . ?
C11 C12 1.5364(19) . ?
C11 H11B 0.982(15) . ?
C11 H11A 0.982(15) . ?
C12 C13 1.5297(17) . ?
C12 H12B 0.942(15) . ?
C12 H12A 0.942(14) . ?
C13 C14 1.5428(15) . ?
C13 C22 1.5436(17) . ?
C13 C17 1.5487(18) . ?
C14 C15 1.5306(15) . ?
C14 H14 1.010(19) . ?
C15 C16 1.5477(16) . ?
C15 H15B 0.968(14) . ?
C15 H15A 0.968(14) . ?
C16 C17 1.5614(16) . ?
C16 C20 1.5618(17) . ?
C16 H16 1.02(2) . ?
C17 C18 1.5236(17) . ?
C17 H17 1.00(2) . ?
C18 C19 1.511(2) . ?
C19 C20 1.5375(18) . ?
C19 H19A 0.960(16) . ?
C19 H19B 0.960(16) . ?
C20 C23 1.5057(18) . ?
C20 H20 0.97(2) . ?
C21 H21A 0.991(14) . ?
C21 H21B 0.991(14) . ?
C21 H21C 0.991(14) . ?
C22 H22A 0.968(14) . ?
C22 H22B 0.968(14) . ?
C22 H22C 0.968(14) . ?
C23 C24 1.3935(18) . ?
C23 C28 1.4010(18) . ?
C24 C25 1.386(2) . ?
C25 C26 1.392(3) . ?
C25 H25 0.97(3) . ?
C26 C27 1.381(3) . ?
C26 H26 0.97(3) . ?
C27 C28 1.390(2) . ?
C27 H27 0.97(3) . ?

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
C2 C1 C10 113.38(11) . . ?
C2 C1 H1A 108.9 . . ?
C10 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
C10 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C3 C2 C1 112.32(11) . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
O1 C3 C4 121.13(15) . . ?
O1 C3 C2 121.94(14) . . ?
C4 C3 C2 116.80(12) . . ?
C5 C4 C3 123.26(13) . . ?
C5 C4 H4 118.4 . . ?
C3 C4 H4 118.4 . . ?
C4 C5 C6 120.20(11) . . ?
C4 C5 C10 122.71(11) . . ?
C6 C5 C10 117.03(10) . . ?
C5 C6 C7 111.90(9) . . ?
C5 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
H6B C6 H6A 107.9 . . ?
C8 C7 C6 110.69(9) . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C14 C8 C7 111.12(9) . . ?
C14 C8 C9 108.88(8) . . ?
C7 C8 C9 110.03(9) . . ?
C14 C8 H8 108.9 . . ?
C7 C8 H8 108.9 . . ?
C9 C8 H8 108.9 . . ?
C11 C9 C8 111.97(10) . . ?
C11 C9 C10 112.92(9) . . ?
C8 C9 C10 113.92(9) . . ?
C11 C9 H9 105.7 . . ?
C8 C9 H9 105.7 . . ?
C10 C9 H9 105.7 . . ?
C5 C10 C1 109.97(10) . . ?
C5 C10 C21 107.68(9) . . ?
C1 C10 C21 109.85(10) . . ?
C5 C10 C9 108.88(9) . . ?
C1 C10 C9 108.47(9) . . ?
C21 C10 C9 111.98(10) . . ?
C12 C11 C9 112.65(10) . . ?
C12 C11 H11B 109.1 . . ?
C9 C11 H11B 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C9 C11 H11A 109.1 . . ?
H11B C11 H11A 107.8 . . ?
C13 C12 C11 110.44(10) . . ?
C13 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
H12B C12 H12A 108.1 . . ?
C12 C13 C14 108.32(9) . . ?
C12 C13 C22 110.14(10) . . ?
C14 C13 C22 112.76(10) . . ?
C12 C13 C17 118.44(10) . . ?
C14 C13 C17 100.94(9) . . ?
C22 C13 C17 106.06(10) . . ?
C8 C14 C15 118.15(9) . . ?
C8 C14 C13 113.68(9) . . ?
C15 C14 C13 103.96(9) . . ?
C8 C14 H14 106.8 . . ?
C15 C14 H14 106.8 . . ?
C13 C14 H14 106.8 . . ?
C14 C15 C16 103.28(9) . . ?
C14 C15 H15B 111.1 . . ?
C16 C15 H15B 111.1 . . ?
C14 C15 H15A 111.1 . . ?
C16 C15 H15A 111.1 . . ?
H15B C15 H15A 109.1 . . ?
C15 C16 C17 106.32(9) . . ?
C15 C16 C20 112.26(9) . . ?
C17 C16 C20 105.84(9) . . ?
C15 C16 H16 110.7 . . ?
C17 C16 H16 110.7 . . ?
C20 C16 H16 110.7 . . ?
C18 C17 C13 119.51(10) . . ?
C18 C17 C16 105.46(10) . . ?
C13 C17 C16 105.45(9) . . ?
C18 C17 H17 108.6 . . ?
C13 C17 H17 108.6 . . ?
C16 C17 H17 108.6 . . ?
O2 C18 C19 124.87(12) . . ?
O2 C18 C17 126.31(12) . . ?
C19 C18 C17 108.80(10) . . ?
C18 C19 C20 103.54(10) . . ?
C18 C19 H19A 111.1 . . ?
C20 C19 H19A 111.1 . . ?
C18 C19 H19B 111.1 . . ?
C20 C19 H19B 111.1 . . ?
H19A C19 H19B 109.0 . . ?
C23 C20 C19 115.58(10) . . ?
C23 C20 C16 113.58(10) . . ?
C19 C20 C16 106.57(10) . . ?
C23 C20 H20 106.9 . . ?
C19 C20 H20 106.9 . . ?
C16 C20 H20 106.9 . . ?
C10 C21 H21A 109.5 . . ?
C10 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C10 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C13 C22 H22A 109.5 . . ?
C13 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C13 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C28 114.65(12) . . ?
C24 C23 C20 122.74(11) . . ?
C28 C23 C20 122.58(12) . . ?
F1A C24 C25 118.04(16) . . ?
F1A C24 C23 117.44(15) . . ?
C25 C24 C23 124.49(14) . . ?
C25 C24 Cl1B 115.85(14) . . ?
C23 C24 Cl1B 119.50(13) . . ?
C24 C25 C26 118.16(15) . . ?
C24 C25 H25 120.9 . . ?
C26 C25 H25 120.9 . . ?
C27 C26 C25 120.21(14) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C28 119.52(15) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
F1B C28 C27 113.9(3) . . ?
F1B C28 C23 123.1(3) . . ?
C27 C28 C23 122.98(14) . . ?
C27 C28 Cl1A 117.64(12) . . ?
C23 C28 Cl1A 119.38(11) . . ?

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
C10 C1 C2 C3 -53.12(16) . . . . ?
C1 C2 C3 O1 -156.19(14) . . . . ?
C1 C2 C3 C4 27.96(17) . . . . ?
O1 C3 C4 C5 -173.62(13) . . . . ?
C2 C3 C4 C5 2.26(19) . . . . ?
C3 C4 C5 C6 169.14(11) . . . . ?
C3 C4 C5 C10 -7.97(18) . . . . ?
C4 C5 C6 C7 131.03(12) . . . . ?
C10 C5 C6 C7 -51.70(14) . . . . ?
C5 C6 C7 C8 55.02(13) . . . . ?
C6 C7 C8 C14 -178.03(9) . . . . ?
C6 C7 C8 C9 -57.36(12) . . . . ?
C14 C8 C9 C11 -52.29(12) . . . . ?
C7 C8 C9 C11 -174.30(9) . . . . ?
C14 C8 C9 C10 178.04(9) . . . . ?
C7 C8 C9 C10 56.03(12) . . . . ?
C4 C5 C10 C1 -16.74(15) . . . . ?
C6 C5 C10 C1 166.06(10) . . . . ?
C4 C5 C10 C21 102.92(13) . . . . ?
C6 C5 C10 C21 -74.27(12) . . . . ?
C4 C5 C10 C9 -135.47(11) . . . . ?
C6 C5 C10 C9 47.34(13) . . . . ?
C2 C1 C10 C5 46.60(14) . . . . ?
C2 C1 C10 C21 -71.74(14) . . . . ?
C2 C1 C10 C9 165.58(11) . . . . ?
C11 C9 C10 C5 -178.34(10) . . . . ?
C8 C9 C10 C5 -49.15(12) . . . . ?
C11 C9 C10 C1 62.00(13) . . . . ?
C8 C9 C10 C1 -168.80(10) . . . . ?
C11 C9 C10 C21 -59.38(13) . . . . ?
C8 C9 C10 C21 69.81(12) . . . . ?
C8 C9 C11 C12 53.41(13) . . . . ?
C10 C9 C11 C12 -176.40(10) . . . . ?
C9 C11 C12 C13 -55.91(14) . . . . ?
C11 C12 C13 C14 57.17(13) . . . . ?
C11 C12 C13 C22 -66.58(13) . . . . ?
C11 C12 C13 C17 171.16(10) . . . . ?
C7 C8 C14 C15 -59.28(13) . . . . ?
C9 C8 C14 C15 179.38(10) . . . . ?
C7 C8 C14 C13 178.48(9) . . . . ?
C9 C8 C14 C13 57.14(12) . . . . ?
C12 C13 C14 C8 -60.12(12) . . . . ?
C22 C13 C14 C8 62.04(13) . . . . ?
C17 C13 C14 C8 174.79(9) . . . . ?
C12 C13 C14 C15 170.09(9) . . . . ?
C22 C13 C14 C15 -67.75(13) . . . . ?
C17 C13 C14 C15 45.00(10) . . . . ?
C8 C14 C15 C16 -166.43(9) . . . . ?
C13 C14 C15 C16 -39.39(11) . . . . ?
C14 C15 C16 C17 18.06(12) . . . . ?
C14 C15 C16 C20 -97.23(11) . . . . ?
C12 C13 C17 C18 -32.52(15) . . . . ?
C14 C13 C17 C18 85.43(12) . . . . ?
C22 C13 C17 C18 -156.82(11) . . . . ?
C12 C13 C17 C16 -150.83(10) . . . . ?
C14 C13 C17 C16 -32.88(11) . . . . ?
C22 C13 C17 C16 84.87(11) . . . . ?
C15 C16 C17 C18 -117.84(10) . . . . ?
C20 C16 C17 C18 1.72(12) . . . . ?
C15 C16 C17 C13 9.51(11) . . . . ?
C20 C16 C17 C13 129.07(9) . . . . ?
C13 C17 C18 O2 42.75(17) . . . . ?
C16 C17 C18 O2 161.05(12) . . . . ?
C13 C17 C18 C19 -139.01(11) . . . . ?
C16 C17 C18 C19 -20.71(13) . . . . ?
O2 C18 C19 C20 -150.42(13) . . . . ?
C17 C18 C19 C20 31.31(13) . . . . ?
C18 C19 C20 C23 -156.66(11) . . . . ?
C18 C19 C20 C16 -29.43(13) . . . . ?
C15 C16 C20 C23 -98.78(11) . . . . ?
C17 C16 C20 C23 145.64(10) . . . . ?
C15 C16 C20 C19 132.81(10) . . . . ?
C17 C16 C20 C19 17.23(12) . . . . ?
C19 C20 C23 C24 61.61(16) . . . . ?
C16 C20 C23 C24 -62.03(15) . . . . ?
C19 C20 C23 C28 -120.26(13) . . . . ?
C16 C20 C23 C28 116.10(13) . . . . ?
C28 C23 C24 F1A -177.87(15) . . . . ?
C20 C23 C24 F1A 0.4(2) . . . . ?
C28 C23 C24 C25 -0.2(2) . . . . ?
C20 C23 C24 C25 178.08(13) . . . . ?
C28 C23 C24 Cl1B 175.03(13) . . . . ?
C20 C23 C24 Cl1B -6.7(2) . . . . ?
F1A C24 C25 C26 177.71(16) . . . . ?
C23 C24 C25 C26 0.0(2) . . . . ?
Cl1B C24 C25 C26 -175.34(14) . . . . ?
C24 C25 C26 C27 0.0(2) . . . . ?
C25 C26 C27 C28 0.1(2) . . . . ?
C26 C27 C28 F1B 179.9(3) . . . . ?
C26 C27 C28 C23 -0.3(2) . . . . ?
C26 C27 C28 Cl1A 179.41(12) . . . . ?
C24 C23 C28 F1B -179.9(3) . . . . ?
C20 C23 C28 F1B 1.8(4) . . . . ?
C24 C23 C28 C27 0.32(19) . . . . ?
C20 C23 C28 C27 -177.95(13) . . . . ?
C24 C23 C28 Cl1A -179.40(10) . . . . ?
C20 C23 C28 Cl1A 2.33(17) . . . . ?

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.043



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2b
_database_code_depnum_ccdc_archive 'CCDC 2060477'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-02-02 deposited with the CCDC.	2022-02-02 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_DIFMX02_2b                  
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*0.75
RESPONSE: This is due to the presence of unresolved minor twinning components.
;
_vrf_PLAT094_2b                  
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       3.11 Report
RESPONSE: This is due to the presence of unresolved minor twinning components.
;
_vrf_PLAT097_2b                  
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.40 eA-3
RESPONSE: Four highest peaks of residual electron density (1.40-0.99 eA-3)
are likely due to the presence of unresolved minor twinning components. 
Most other peaks (0.54 eA-3 and below) are located on / near bonds.
;
_vrf_PLAT340_2b                  
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00448 Ang.
RESPONSE: The selected crystal was a weakly diffracting very thin plate.
;
_vrf_PLAT911_2b                  
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
RESPONSE: Reflections 0 1 2 and 0 1 3 were hidden behind the beamstop.
;
_vrf_PLAT910_2b                  
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).          6 Note  
RESPONSE: Five reflections were hidden behind the beamstop. 
Reflection  0 0 2 was omitted as I(obs) was much smaller than I(calc).
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H32 Cl F O2'
_chemical_formula_sum            'C28 H32 Cl F O2'
_chemical_formula_weight         454.98

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.3425(4)
_cell_length_b                   19.7162(12)
_cell_length_c                   31.4052(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4546.4(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9717
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      31.86

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             1936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.200
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6097
_exptl_absorpt_correction_T_max  0.7470
_exptl_absorpt_process_details   
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-Ray tube'
_diffrn_source_power             50
_diffrn_source_current           30
_diffrn_source_size              '0.6 mm, fine-focus'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            126091
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_theta_min         2.439
_diffrn_reflns_theta_max         34.347
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             19060
_reflns_number_gt                14999
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    
'SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0709P)²+4.1754P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 5401 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack, Wagner, Acta Cryst., 2013, B69, 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_chemical_absolute_configuration synad
_refine_ls_number_reflns         19060
_refine_ls_number_parameters     621
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1694
_refine_ls_wR_factor_gt          0.1540
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cl1A Cl 0.69763(11) 0.46687(4) 0.49761(3) 0.02528(15) Uani 1 1 d . . . . .
F1A F 0.2183(4) 0.71783(13) 0.45920(9) 0.0436(6) Uani 1 1 d . . . . .
O1A O 0.7412(4) -0.00638(17) 0.69660(11) 0.0418(7) Uani 1 1 d . . . . .
O2A O 0.8258(3) 0.48645(14) 0.59079(9) 0.0285(5) Uani 1 1 d . . . . .
C1A C 0.8733(4) 0.12608(18) 0.62279(14) 0.0297(7) Uani 1 1 d . . . . .
H1A H 0.958(3) 0.1312(3) 0.6016(8) 0.036 Uiso 1 1 calc R U . . .
H1B H 0.9074(14) 0.1532(10) 0.6451(8) 0.036 Uiso 1 1 calc R U . . .
C2A C 0.8742(5) 0.0523(2) 0.63757(15) 0.0343(8) Uani 1 1 d . . . . .
H2A H 0.8570(8) 0.0225(11) 0.6128(9) 0.041 Uiso 1 1 calc R U . . .
H2B H 0.993(4) 0.0417(4) 0.6502(5) 0.041 Uiso 1 1 calc R U . . .
C3A C 0.7271(5) 0.0382(2) 0.66971(13) 0.0294(7) Uani 1 1 d . . . . .
C4A C 0.5626(5) 0.0791(2) 0.66583(12) 0.0279(7) Uani 1 1 d . . . . .
H4A H 0.468(5) 0.0706(5) 0.6849(10) 0.033 Uiso 1 1 calc R U . . .
C5A C 0.5382(4) 0.12811(18) 0.63688(11) 0.0237(6) Uani 1 1 d . . . . .
C6A C 0.3541(5) 0.1610(2) 0.63214(13) 0.0301(7) Uani 1 1 d . . . . .
H6B H 0.278(3) 0.1498(4) 0.6578(9) 0.036 Uiso 1 1 calc R U . . .
H6A H 0.292(2) 0.1415(7) 0.6065(9) 0.036 Uiso 1 1 calc R U . . .
C7A C 0.3641(4) 0.23825(18) 0.62732(12) 0.0275(7) Uani 1 1 d . . . . .
H7A H 0.4056(15) 0.2591(7) 0.6549(10) 0.033 Uiso 1 1 calc R U . . .
H7B H 0.240(4) 0.2566(7) 0.6205(3) 0.033 Uiso 1 1 calc R U . . .
C8A C 0.4972(4) 0.25737(17) 0.59168(11) 0.0218(6) Uani 1 1 d . . . . .
H8A H 0.456(2) 0.2357(10) 0.5652(12) 0.026 Uiso 1 1 calc R U . . .
C9A C 0.6877(4) 0.22885(16) 0.60303(10) 0.0191(5) Uani 1 1 d . . . . .
H9A H 0.7157(13) 0.2456(8) 0.6319(13) 0.023 Uiso 1 1 calc R U . . .
C10A C 0.6870(4) 0.15013(16) 0.60610(10) 0.0208(5) Uani 1 1 d . . . . .
C11A C 0.8404(4) 0.25600(17) 0.57394(12) 0.0245(6) Uani 1 1 d . . . . .
H11B H 0.962(4) 0.2436(4) 0.5869(4) 0.029 Uiso 1 1 calc R U . . .
H11A H 0.8316(5) 0.2324(8) 0.5453(9) 0.029 Uiso 1 1 calc R U . . .
C12A C 0.8357(4) 0.33303(17) 0.56657(11) 0.0239(6) Uani 1 1 d . . . . .
H12B H 0.8622(9) 0.3576(8) 0.5943(9) 0.029 Uiso 1 1 calc R U . . .
H12A H 0.932(3) 0.3463(5) 0.5451(7) 0.029 Uiso 1 1 calc R U . . .
C13A C 0.6471(4) 0.35344(16) 0.55001(10) 0.0196(5) Uani 1 1 d . . . . .
C14A C 0.5066(4) 0.33347(17) 0.58427(10) 0.0211(6) Uani 1 1 d . . . . .
H14A H 0.5452(17) 0.3551(10) 0.6117(12) 0.025 Uiso 1 1 calc R U . . .
C15A C 0.3302(4) 0.36854(18) 0.56975(12) 0.0264(6) Uani 1 1 d . . . . .
H15B H 0.257(3) 0.3786(4) 0.5930(8) 0.032 Uiso 1 1 calc R U . . .
H15A H 0.266(2) 0.3408(10) 0.5512(7) 0.032 Uiso 1 1 calc R U . . .
C16A C 0.3914(4) 0.43462(17) 0.54690(11) 0.0214(5) Uani 1 1 d . . . . .
H16A H 0.342(2) 0.43647(19) 0.5188(13) 0.026 Uiso 1 1 calc R U . . .
C17A C 0.6029(4) 0.42959(16) 0.54512(10) 0.0201(5) Uani 1 1 d . . . . .
C18A C 0.6687(4) 0.47622(17) 0.58196(10) 0.0223(6) Uani 1 1 d . . . . .
C19A C 0.5040(5) 0.5074(2) 0.60333(11) 0.0276(7) Uani 1 1 d . . . . .
H19A H 0.5269(9) 0.5558(16) 0.6100(3) 0.033 Uiso 1 1 calc R U . . .
H19B H 0.4756(11) 0.4832(8) 0.6302(9) 0.033 Uiso 1 1 calc R U . . .
C20A C 0.3459(4) 0.50060(17) 0.57164(11) 0.0235(6) Uani 1 1 d . . . . .
H20A H 0.238(6) 0.4939(4) 0.5869(8) 0.028 Uiso 1 1 calc R U . . .
C21A C 0.6456(6) 0.1163(2) 0.56261(12) 0.0318(7) Uani 1 1 d . . . . .
H21A H 0.531(4) 0.1309(15) 0.5527(6) 0.048 Uiso 1 1 calc R U . . .
H21B H 0.645(5) 0.0688(15) 0.5659(3) 0.048 Uiso 1 1 calc R U . . .
H21C H 0.736(4) 0.1285(16) 0.5428(7) 0.048 Uiso 1 1 calc R U . . .
C22A C 0.6111(5) 0.31891(18) 0.50689(11) 0.0266(6) Uani 1 1 d . . . . .
H22A H 0.500(4) 0.3365(13) 0.4947(6) 0.040 Uiso 1 1 calc R U . . .
H22B H 0.600(5) 0.2705(14) 0.5110(2) 0.040 Uiso 1 1 calc R U . . .
H22C H 0.711(4) 0.3280(14) 0.4878(7) 0.040 Uiso 1 1 calc R U . . .
C23A C 0.3205(4) 0.56024(17) 0.54186(10) 0.0219(5) Uani 1 1 d . . . . .
C24A C 0.4419(5) 0.61417(19) 0.53823(12) 0.0288(7) Uani 1 1 d . . . . .
H24A H 0.543(6) 0.61458(19) 0.5541(9) 0.035 Uiso 1 1 calc R U . . .
C25A C 0.4077(6) 0.6675(2) 0.51025(14) 0.0341(8) Uani 1 1 d . . . . .
H25A H 0.500(5) 0.708(2) 0.5075(2) 0.041 Uiso 1 1 calc R U . . .
C26A C 0.2513(6) 0.6654(2) 0.48628(13) 0.0318(7) Uani 1 1 d . . . . .
C27A C 0.1267(5) 0.6135(2) 0.48882(12) 0.0296(7) Uani 1 1 d . . . . .
H27A H 0.015(6) 0.6138(2) 0.4712(9) 0.036 Uiso 1 1 calc R U . . .
C28A C 0.1623(5) 0.56094(18) 0.51676(11) 0.0253(6) Uani 1 1 d . . . . .
H28A H 0.075(4) 0.5233(19) 0.51907(16) 0.030 Uiso 1 1 calc R U . . .
Cl1B Cl 0.35797(10) 0.72323(4) 0.31097(3) 0.02160(14) Uani 1 1 d . . . . .
F1B F 0.8535(5) 0.51551(11) 0.40285(9) 0.0455(6) Uani 1 1 d . . . . .
O1B O 0.1368(4) 1.28393(12) 0.27869(9) 0.0311(5) Uani 1 1 d . . . . .
O2B O 0.2118(3) 0.81819(12) 0.38417(8) 0.0249(5) Uani 1 1 d . . . . .
C1B C 0.0685(4) 1.10226(16) 0.26738(11) 0.0207(5) Uani 1 1 d . . . . .
H1C H -0.006(3) 1.0747(9) 0.2519(5) 0.025 Uiso 1 1 calc R U . . .
H1D H 0.0350(12) 1.0989(2) 0.2952(9) 0.025 Uiso 1 1 calc R U . . .
C2B C 0.0421(4) 1.17551(16) 0.25263(11) 0.0222(6) Uani 1 1 d . . . . .
H2C H 0.0611(7) 1.17798(18) 0.2222(10) 0.027 Uiso 1 1 calc R U . . .
H2D H -0.082(4) 1.1894(5) 0.2584(2) 0.027 Uiso 1 1 calc R U . . .
C3B C 0.1710(4) 1.22353(16) 0.27451(10) 0.0210(5) Uani 1 1 d . . . . .
C4B C 0.3451(4) 1.19479(15) 0.28851(10) 0.0201(5) Uani 1 1 d . . . . .
H4B H 0.429(4) 1.2241(14) 0.3042(7) 0.024 Uiso 1 1 calc R U . . .
C5B C 0.3959(4) 1.13025(15) 0.28100(10) 0.0177(5) Uani 1 1 d . . . . .
C6B C 0.5899(4) 1.10892(16) 0.28777(11) 0.0209(6) Uani 1 1 d . . . . .
H6D H 0.653(2) 1.1439(11) 0.3040(5) 0.025 Uiso 1 1 calc R U . . .
H6C H 0.6501(19) 1.1049(2) 0.2602(9) 0.025 Uiso 1 1 calc R U . . .
C7B C 0.6054(4) 1.04131(15) 0.31150(11) 0.0198(5) Uani 1 1 d . . . . .
H7C H 0.735(4) 1.0267(5) 0.31212(11) 0.024 Uiso 1 1 calc R U . . .
H7D H 0.5639(13) 1.0474(2) 0.3414(9) 0.024 Uiso 1 1 calc R U . . .
C8B C 0.4907(4) 0.98672(15) 0.29009(10) 0.0167(5) Uani 1 1 d . . . . .
H8B H 0.5344(19) 0.9797(3) 0.2617(12) 0.020 Uiso 1 1 calc R U . . .
C9B C 0.2898(4) 1.01036(14) 0.28820(10) 0.0163(5) Uani 1 1 d . . . . .
H9B H 0.2557(16) 1.0199(5) 0.3159(13) 0.020 Uiso 1 1 calc R U . . .
C10B C 0.2667(4) 1.07772(15) 0.26257(10) 0.0174(5) Uani 1 1 d . . . . .
C11B C 0.1613(4) 0.95402(15) 0.27245(11) 0.0204(5) Uani 1 1 d . . . . .
H11D H 0.033(4) 0.9701(5) 0.27507(13) 0.024 Uiso 1 1 calc R U . . .
H11C H 0.1859(8) 0.9454(3) 0.2416(10) 0.024 Uiso 1 1 calc R U . . .
C12B C 0.1817(4) 0.88712(15) 0.29704(10) 0.0194(5) Uani 1 1 d . . . . .
H12D H 0.1424(13) 0.8936(2) 0.3264(9) 0.023 Uiso 1 1 calc R U . . .
H12C H 0.104(2) 0.8525(11) 0.2842(4) 0.023 Uiso 1 1 calc R U . . .
C13B C 0.3795(4) 0.86346(14) 0.29635(9) 0.0167(5) Uani 1 1 d . . . . .
C14B C 0.5009(4) 0.92010(14) 0.31460(10) 0.0163(5) Uani 1 1 d . . . . .
H14B H 0.4580(19) 0.9292(4) 0.3426(12) 0.020 Uiso 1 1 calc R U . . .
C15B C 0.6882(4) 0.88625(15) 0.31925(11) 0.0200(5) Uani 1 1 d . . . . .
H15D H 0.756(2) 0.9071(7) 0.3410(7) 0.024 Uiso 1 1 calc R U . . .
H15C H 0.754(2) 0.88917(18) 0.2936(8) 0.024 Uiso 1 1 calc R U . . .
C16B C 0.6467(4) 0.81065(14) 0.33060(10) 0.0182(5) Uani 1 1 d . . . . .
H16B H 0.704(3) 0.7809(14) 0.3114(9) 0.022 Uiso 1 1 calc R U . . .
C17B C 0.4368(4) 0.80586(14) 0.32693(10) 0.0164(5) Uani 1 1 d . . . . .
C18B C 0.3692(4) 0.81512(14) 0.37349(10) 0.0193(5) Uani 1 1 d . . . . .
C19B C 0.5330(4) 0.82101(16) 0.40245(10) 0.0216(6) Uani 1 1 d . . . . .
H19C H 0.5136(8) 0.7951(9) 0.4285(9) 0.026 Uiso 1 1 calc R U . . .
H19D H 0.5544(8) 0.8683(15) 0.4100(3) 0.026 Uiso 1 1 calc R U . . .
C20B C 0.6955(4) 0.79256(15) 0.37763(10) 0.0196(5) Uani 1 1 d . . . . .
H20B H 0.804(5) 0.8176(12) 0.3857(4) 0.024 Uiso 1 1 calc R U . . .
C21B C 0.3123(5) 1.06871(16) 0.21487(10) 0.0217(5) Uani 1 1 d . . . . .
H21D H 0.437(4) 1.0509(15) 0.21193(13) 0.033 Uiso 1 1 calc R U . . .
H21E H 0.303(4) 1.1127(12) 0.2004(5) 0.033 Uiso 1 1 calc R U . . .
H21F H 0.226(3) 1.0367(15) 0.2020(4) 0.033 Uiso 1 1 calc R U . . .
C22B C 0.4333(5) 0.84408(17) 0.25041(10) 0.0218(6) Uani 1 1 d . . . . .
H22D H 0.559(4) 0.8285(15) 0.25000(19) 0.033 Uiso 1 1 calc R U . . .
H22E H 0.421(4) 0.8834(12) 0.2321(6) 0.033 Uiso 1 1 calc R U . . .
H22F H 0.354(3) 0.8081(14) 0.2403(5) 0.033 Uiso 1 1 calc R U . . .
C23B C 0.7308(4) 0.71777(16) 0.38436(10) 0.0201(5) Uani 1 1 d . . . . .
C24B C 0.6038(5) 0.67392(17) 0.40223(12) 0.0258(6) Uani 1 1 d . . . . .
H24B H 0.489(6) 0.6906(9) 0.4102(4) 0.031 Uiso 1 1 calc R U . . .
C25B C 0.6441(6) 0.60501(17) 0.40861(12) 0.0307(7) Uani 1 1 d . . . . .
H25B H 0.557(5) 0.5752(17) 0.4210(7) 0.037 Uiso 1 1 calc R U . . .
C26B C 0.8121(6) 0.58226(18) 0.39648(12) 0.0305(7) Uani 1 1 d . . . . .
C27B C 0.9433(5) 0.62331(19) 0.37839(12) 0.0297(7) Uani 1 1 d . . . . .
H27B H 1.069(6) 0.6040(10) 0.3692(5) 0.036 Uiso 1 1 calc R U . . .
C28B C 0.9007(4) 0.69176(18) 0.37290(11) 0.0238(6) Uani 1 1 d . . . . .
H28B H 0.987(5) 0.7206(15) 0.3614(6) 0.029 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Cl1A C17A 1.803(3) . ?
F1A C26A 1.360(5) . ?
O1A C3A 1.223(5) . ?
O2A C18A 1.204(4) . ?
C1A C2A 1.526(5) . ?
C1A C10A 1.540(5) . ?
C1A H1A 0.92(3) . ?
C1A H1B 0.92(3) . ?
C2A C3A 1.504(5) . ?
C2A H2A 0.98(4) . ?
C2A H2B 0.98(4) . ?
C3A C4A 1.457(5) . ?
C4A C5A 1.338(5) . ?
C4A H4A 0.94(5) . ?
C5A C6A 1.506(5) . ?
C5A C10A 1.522(4) . ?
C6A C7A 1.532(5) . ?
C6A H6B 1.00(3) . ?
C6A H6A 1.00(3) . ?
C7A C8A 1.533(5) . ?
C7A H7A 1.01(3) . ?
C7A H7B 1.01(3) . ?
C8A C14A 1.520(5) . ?
C8A C9A 1.549(4) . ?
C8A H8A 0.98(5) . ?
C9A C11A 1.542(4) . ?
C9A C10A 1.555(4) . ?
C9A H9A 0.99(4) . ?
C10A C21A 1.550(5) . ?
C11A C12A 1.537(5) . ?
C11A H11B 1.01(3) . ?
C11A H11A 1.01(3) . ?
C12A C13A 1.533(4) . ?
C12A H12B 1.01(3) . ?
C12A H12A 1.01(3) . ?
C13A C22A 1.538(4) . ?
C13A C14A 1.541(4) . ?
C13A C17A 1.544(5) . ?
C14A C15A 1.537(4) . ?
C14A H14A 1.00(4) . ?
C15A C16A 1.554(5) . ?
C15A H15B 0.93(3) . ?
C15A H15A 0.93(3) . ?
C16A C20A 1.552(5) . ?
C16A C17A 1.557(4) . ?
C16A H16A 0.96(4) . ?
C17A C18A 1.555(4) . ?
C18A C19A 1.514(5) . ?
C19A C20A 1.535(5) . ?
C19A H19A 0.99(3) . ?
C19A H19B 0.99(3) . ?
C20A C23A 1.514(5) . ?
C20A H20A 0.94(5) . ?
C21A H21A 0.94(3) . ?
C21A H21B 0.94(3) . ?
C21A H21C 0.94(3) . ?
C22A H22A 0.97(3) . ?
C22A H22B 0.97(3) . ?
C22A H22C 0.97(3) . ?
C23A C24A 1.392(5) . ?
C23A C28A 1.404(4) . ?
C24A C25A 1.393(6) . ?
C24A H24A 0.89(5) . ?
C25A C26A 1.374(6) . ?
C25A H25A 1.06(5) . ?
C26A C27A 1.374(6) . ?
C27A C28A 1.384(5) . ?
C27A H27A 0.99(5) . ?
C28A H28A 0.98(5) . ?
Cl1B C17B 1.800(3) . ?
F1B C26B 1.365(4) . ?
O1B C3B 1.224(4) . ?
O2B C18B 1.205(4) . ?
C1B C2B 1.529(4) . ?
C1B C10B 1.541(4) . ?
C1B H1C 0.91(3) . ?
C1B H1D 0.91(3) . ?
C2B C3B 1.505(5) . ?
C2B H2C 0.97(3) . ?
C2B H2D 0.97(3) . ?
C3B C4B 1.466(4) . ?
C4B C5B 1.347(4) . ?
C4B H4B 0.98(5) . ?
C5B C6B 1.501(4) . ?
C5B C10B 1.519(4) . ?
C6B C7B 1.531(4) . ?
C6B H6D 0.97(3) . ?
C6B H6C 0.97(3) . ?
C7B C8B 1.523(4) . ?
C7B H7C 0.99(3) . ?
C7B H7D 0.99(3) . ?
C8B C14B 1.524(4) . ?
C8B C9B 1.548(4) . ?
C8B H8B 0.96(4) . ?
C9B C11B 1.539(4) . ?
C9B C10B 1.562(4) . ?
C9B H9B 0.93(4) . ?
C10B C21B 1.545(4) . ?
C11B C12B 1.536(4) . ?
C11B H11D 1.00(3) . ?
C11B H11C 1.00(3) . ?
C12B C13B 1.526(4) . ?
C12B H12D 0.98(3) . ?
C12B H12C 0.98(3) . ?
C13B C14B 1.539(4) . ?
C13B C22B 1.544(4) . ?
C13B C17B 1.546(4) . ?
C14B C15B 1.536(4) . ?
C14B H14B 0.95(4) . ?
C15B C16B 1.563(4) . ?
C15B H15D 0.94(3) . ?
C15B H15C 0.94(3) . ?
C16B C17B 1.549(4) . ?
C16B C20B 1.561(4) . ?
C16B H16B 0.94(4) . ?
C17B C18B 1.555(4) . ?
C18B C19B 1.512(5) . ?
C19B C20B 1.532(5) . ?
C19B H19C 0.98(3) . ?
C19B H19D 0.98(3) . ?
C20B C23B 1.512(4) . ?
C20B H20B 0.97(5) . ?
C21B H21D 0.98(3) . ?
C21B H21E 0.98(3) . ?
C21B H21F 0.98(3) . ?
C22B H22D 0.97(3) . ?
C22B H22E 0.97(3) . ?
C22B H22F 0.97(3) . ?
C23B C24B 1.390(5) . ?
C23B C28B 1.396(4) . ?
C24B C25B 1.405(5) . ?
C24B H24B 0.94(5) . ?
C25B C26B 1.367(6) . ?
C25B H25B 0.95(5) . ?
C26B C27B 1.381(6) . ?
C27B C28B 1.396(5) . ?
C27B H27B 1.04(5) . ?
C28B H28B 0.93(5) . ?

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
C2A C1A C10A 113.6(3) . . ?
C2A C1A H1A 108.8 . . ?
C10A C1A H1A 108.8 . . ?
C2A C1A H1B 108.8 . . ?
C10A C1A H1B 108.8 . . ?
H1A C1A H1B 107.7 . . ?
C3A C2A C1A 112.2(3) . . ?
C3A C2A H2A 109.2 . . ?
C1A C2A H2A 109.2 . . ?
C3A C2A H2B 109.2 . . ?
C1A C2A H2B 109.2 . . ?
H2A C2A H2B 107.9 . . ?
O1A C3A C4A 121.7(4) . . ?
O1A C3A C2A 122.4(4) . . ?
C4A C3A C2A 115.9(3) . . ?
C5A C4A C3A 124.6(3) . . ?
C5A C4A H4A 117.7 . . ?
C3A C4A H4A 117.7 . . ?
C4A C5A C6A 119.9(3) . . ?
C4A C5A C10A 122.7(3) . . ?
C6A C5A C10A 117.3(3) . . ?
C5A C6A C7A 113.3(3) . . ?
C5A C6A H6B 108.9 . . ?
C7A C6A H6B 108.9 . . ?
C5A C6A H6A 108.9 . . ?
C7A C6A H6A 108.9 . . ?
H6B C6A H6A 107.7 . . ?
C6A C7A C8A 110.3(3) . . ?
C6A C7A H7A 109.6 . . ?
C8A C7A H7A 109.6 . . ?
C6A C7A H7B 109.6 . . ?
C8A C7A H7B 109.6 . . ?
H7A C7A H7B 108.1 . . ?
C14A C8A C7A 112.6(3) . . ?
C14A C8A C9A 110.6(2) . . ?
C7A C8A C9A 108.6(3) . . ?
C14A C8A H8A 108.3 . . ?
C7A C8A H8A 108.3 . . ?
C9A C8A H8A 108.3 . . ?
C11A C9A C8A 113.2(3) . . ?
C11A C9A C10A 112.7(2) . . ?
C8A C9A C10A 111.9(2) . . ?
C11A C9A H9A 106.1 . . ?
C8A C9A H9A 106.1 . . ?
C10A C9A H9A 106.1 . . ?
C5A C10A C1A 109.5(3) . . ?
C5A C10A C21A 107.2(3) . . ?
C1A C10A C21A 110.0(3) . . ?
C5A C10A C9A 109.1(3) . . ?
C1A C10A C9A 109.0(2) . . ?
C21A C10A C9A 112.1(3) . . ?
C12A C11A C9A 114.6(3) . . ?
C12A C11A H11B 108.6 . . ?
C9A C11A H11B 108.6 . . ?
C12A C11A H11A 108.6 . . ?
C9A C11A H11A 108.6 . . ?
H11B C11A H11A 107.6 . . ?
C13A C12A C11A 109.3(3) . . ?
C13A C12A H12B 109.8 . . ?
C11A C12A H12B 109.8 . . ?
C13A C12A H12A 109.8 . . ?
C11A C12A H12A 109.8 . . ?
H12B C12A H12A 108.3 . . ?
C12A C13A C22A 109.7(3) . . ?
C12A C13A C14A 107.5(3) . . ?
C22A C13A C14A 112.7(3) . . ?
C12A C13A C17A 118.6(2) . . ?
C22A C13A C17A 107.9(3) . . ?
C14A C13A C17A 100.2(2) . . ?
C8A C14A C15A 116.8(3) . . ?
C8A C14A C13A 112.9(3) . . ?
C15A C14A C13A 104.0(3) . . ?
C8A C14A H14A 107.6 . . ?
C15A C14A H14A 107.6 . . ?
C13A C14A H14A 107.6 . . ?
C14A C15A C16A 105.7(2) . . ?
C14A C15A H15B 110.6 . . ?
C16A C15A H15B 110.6 . . ?
C14A C15A H15A 110.6 . . ?
C16A C15A H15A 110.6 . . ?
H15B C15A H15A 108.7 . . ?
C20A C16A C15A 114.2(3) . . ?
C20A C16A C17A 106.6(2) . . ?
C15A C16A C17A 104.6(3) . . ?
C20A C16A H16A 110.4 . . ?
C15A C16A H16A 110.4 . . ?
C17A C16A H16A 110.4 . . ?
C13A C17A C18A 115.8(3) . . ?
C13A C17A C16A 105.6(2) . . ?
C18A C17A C16A 104.2(2) . . ?
C13A C17A Cl1A 113.4(2) . . ?
C18A C17A Cl1A 104.8(2) . . ?
C16A C17A Cl1A 112.9(2) . . ?
O2A C18A C19A 126.5(3) . . ?
O2A C18A C17A 124.7(3) . . ?
C19A C18A C17A 108.8(3) . . ?
C18A C19A C20A 106.3(3) . . ?
C18A C19A H19A 110.5 . . ?
C20A C19A H19A 110.5 . . ?
C18A C19A H19B 110.5 . . ?
C20A C19A H19B 110.5 . . ?
H19A C19A H19B 108.7 . . ?
C23A C20A C19A 115.2(3) . . ?
C23A C20A C16A 111.6(3) . . ?
C19A C20A C16A 103.6(3) . . ?
C23A C20A H20A 108.7 . . ?
C19A C20A H20A 108.7 . . ?
C16A C20A H20A 108.7 . . ?
C10A C21A H21A 109.5 . . ?
C10A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
C10A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C13A C22A H22A 109.5 . . ?
C13A C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C13A C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
C24A C23A C28A 118.4(3) . . ?
C24A C23A C20A 124.4(3) . . ?
C28A C23A C20A 117.2(3) . . ?
C23A C24A C25A 120.8(3) . . ?
C23A C24A H24A 119.6 . . ?
C25A C24A H24A 119.6 . . ?
C26A C25A C24A 118.3(4) . . ?
C26A C25A H25A 120.9 . . ?
C24A C25A H25A 120.9 . . ?
F1A C26A C25A 118.0(4) . . ?
F1A C26A C27A 118.9(4) . . ?
C25A C26A C27A 123.1(4) . . ?
C26A C27A C28A 117.9(4) . . ?
C26A C27A H27A 121.0 . . ?
C28A C27A H27A 121.0 . . ?
C27A C28A C23A 121.3(3) . . ?
C27A C28A H28A 119.3 . . ?
C23A C28A H28A 119.3 . . ?
C2B C1B C10B 112.7(2) . . ?
C2B C1B H1C 109.0 . . ?
C10B C1B H1C 109.0 . . ?
C2B C1B H1D 109.0 . . ?
C10B C1B H1D 109.0 . . ?
H1C C1B H1D 107.8 . . ?
C3B C2B C1B 112.1(3) . . ?
C3B C2B H2C 109.2 . . ?
C1B C2B H2C 109.2 . . ?
C3B C2B H2D 109.2 . . ?
C1B C2B H2D 109.2 . . ?
H2C C2B H2D 107.9 . . ?
O1B C3B C4B 121.5(3) . . ?
O1B C3B C2B 122.1(3) . . ?
C4B C3B C2B 116.3(3) . . ?
C5B C4B C3B 123.6(3) . . ?
C5B C4B H4B 118.2 . . ?
C3B C4B H4B 118.2 . . ?
C4B C5B C6B 120.2(3) . . ?
C4B C5B C10B 122.6(3) . . ?
C6B C5B C10B 117.1(3) . . ?
C5B C6B C7B 112.5(2) . . ?
C5B C6B H6D 109.1 . . ?
C7B C6B H6D 109.1 . . ?
C5B C6B H6C 109.1 . . ?
C7B C6B H6C 109.1 . . ?
H6D C6B H6C 107.8 . . ?
C8B C7B C6B 111.1(2) . . ?
C8B C7B H7C 109.4 . . ?
C6B C7B H7C 109.4 . . ?
C8B C7B H7D 109.4 . . ?
C6B C7B H7D 109.4 . . ?
H7C C7B H7D 108.0 . . ?
C7B C8B C14B 111.0(2) . . ?
C7B C8B C9B 109.3(2) . . ?
C14B C8B C9B 109.0(2) . . ?
C7B C8B H8B 109.2 . . ?
C14B C8B H8B 109.2 . . ?
C9B C8B H8B 109.2 . . ?
C11B C9B C8B 112.3(2) . . ?
C11B C9B C10B 112.4(2) . . ?
C8B C9B C10B 112.3(2) . . ?
C11B C9B H9B 106.4 . . ?
C8B C9B H9B 106.4 . . ?
C10B C9B H9B 106.4 . . ?
C5B C10B C1B 109.8(2) . . ?
C5B C10B C21B 108.2(2) . . ?
C1B C10B C21B 109.6(2) . . ?
C5B C10B C9B 108.4(2) . . ?
C1B C10B C9B 108.6(2) . . ?
C21B C10B C9B 112.2(2) . . ?
C12B C11B C9B 113.5(2) . . ?
C12B C11B H11D 108.9 . . ?
C9B C11B H11D 108.9 . . ?
C12B C11B H11C 108.9 . . ?
C9B C11B H11C 108.9 . . ?
H11D C11B H11C 107.7 . . ?
C13B C12B C11B 110.4(2) . . ?
C13B C12B H12D 109.6 . . ?
C11B C12B H12D 109.6 . . ?
C13B C12B H12C 109.6 . . ?
C11B C12B H12C 109.6 . . ?
H12D C12B H12C 108.1 . . ?
C12B C13B C14B 108.9(2) . . ?
C12B C13B C22B 109.4(2) . . ?
C14B C13B C22B 112.3(2) . . ?
C12B C13B C17B 118.3(2) . . ?
C14B C13B C17B 98.3(2) . . ?
C22B C13B C17B 109.2(2) . . ?
C8B C14B C15B 117.8(2) . . ?
C8B C14B C13B 114.1(2) . . ?
C15B C14B C13B 103.8(2) . . ?
C8B C14B H14B 106.8 . . ?
C15B C14B H14B 106.8 . . ?
C13B C14B H14B 106.8 . . ?
C14B C15B C16B 105.2(2) . . ?
C14B C15B H15D 110.7 . . ?
C16B C15B H15D 110.7 . . ?
C14B C15B H15C 110.7 . . ?
C16B C15B H15C 110.7 . . ?
H15D C15B H15C 108.8 . . ?
C17B C16B C20B 106.5(2) . . ?
C17B C16B C15B 103.6(2) . . ?
C20B C16B C15B 112.9(2) . . ?
C17B C16B H16B 111.2 . . ?
C20B C16B H16B 111.2 . . ?
C15B C16B H16B 111.2 . . ?
C13B C17B C16B 105.8(2) . . ?
C13B C17B C18B 114.3(2) . . ?
C16B C17B C18B 103.9(2) . . ?
C13B C17B Cl1B 113.9(2) . . ?
C16B C17B Cl1B 113.3(2) . . ?
C18B C17B Cl1B 105.40(19) . . ?
O2B C18B C19B 126.3(3) . . ?
O2B C18B C17B 125.0(3) . . ?
C19B C18B C17B 108.7(3) . . ?
C18B C19B C20B 106.6(3) . . ?
C18B C19B H19C 110.4 . . ?
C20B C19B H19C 110.4 . . ?
C18B C19B H19D 110.4 . . ?
C20B C19B H19D 110.4 . . ?
H19C C19B H19D 108.6 . . ?
C23B C20B C19B 114.8(3) . . ?
C23B C20B C16B 113.2(2) . . ?
C19B C20B C16B 102.7(2) . . ?
C23B C20B H20B 108.6 . . ?
C19B C20B H20B 108.6 . . ?
C16B C20B H20B 108.6 . . ?
C10B C21B H21D 109.5 . . ?
C10B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
C10B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
C13B C22B H22D 109.5 . . ?
C13B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C13B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
C24B C23B C28B 118.4(3) . . ?
C24B C23B C20B 123.2(3) . . ?
C28B C23B C20B 118.4(3) . . ?
C23B C24B C25B 121.2(3) . . ?
C23B C24B H24B 119.4 . . ?
C25B C24B H24B 119.4 . . ?
C26B C25B C24B 117.9(3) . . ?
C26B C25B H25B 121.1 . . ?
C24B C25B H25B 121.1 . . ?
F1B C26B C25B 118.5(4) . . ?
F1B C26B C27B 118.0(4) . . ?
C25B C26B C27B 123.5(3) . . ?
C26B C27B C28B 117.5(3) . . ?
C26B C27B H27B 121.3 . . ?
C28B C27B H27B 121.3 . . ?
C27B C28B C23B 121.6(3) . . ?
C27B C28B H28B 119.2 . . ?
C23B C28B H28B 119.2 . . ?

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
C10A C1A C2A C3A -53.6(5) . . . . ?
C1A C2A C3A O1A -152.3(4) . . . . ?
C1A C2A C3A C4A 30.1(5) . . . . ?
O1A C3A C4A C5A -179.3(4) . . . . ?
C2A C3A C4A C5A -1.7(6) . . . . ?
C3A C4A C5A C6A 172.1(4) . . . . ?
C3A C4A C5A C10A -4.3(6) . . . . ?
C4A C5A C6A C7A 136.8(4) . . . . ?
C10A C5A C6A C7A -46.5(4) . . . . ?
C5A C6A C7A C8A 52.0(4) . . . . ?
C6A C7A C8A C14A 177.7(3) . . . . ?
C6A C7A C8A C9A -59.5(4) . . . . ?
C14A C8A C9A C11A -45.3(4) . . . . ?
C7A C8A C9A C11A -169.2(3) . . . . ?
C14A C8A C9A C10A -173.9(3) . . . . ?
C7A C8A C9A C10A 62.1(3) . . . . ?
C4A C5A C10A C1A -18.2(5) . . . . ?
C6A C5A C10A C1A 165.3(3) . . . . ?
C4A C5A C10A C21A 101.1(4) . . . . ?
C6A C5A C10A C21A -75.5(4) . . . . ?
C4A C5A C10A C9A -137.4(3) . . . . ?
C6A C5A C10A C9A 46.1(4) . . . . ?
C2A C1A C10A C5A 46.4(4) . . . . ?
C2A C1A C10A C21A -71.1(4) . . . . ?
C2A C1A C10A C9A 165.6(3) . . . . ?
C11A C9A C10A C5A 177.5(3) . . . . ?
C8A C9A C10A C5A -53.6(3) . . . . ?
C11A C9A C10A C1A 58.0(4) . . . . ?
C8A C9A C10A C1A -173.1(3) . . . . ?
C11A C9A C10A C21A -64.0(3) . . . . ?
C8A C9A C10A C21A 65.0(3) . . . . ?
C8A C9A C11A C12A 46.3(4) . . . . ?
C10A C9A C11A C12A 174.6(3) . . . . ?
C9A C11A C12A C13A -54.2(4) . . . . ?
C11A C12A C13A C22A -62.3(3) . . . . ?
C11A C12A C13A C14A 60.6(3) . . . . ?
C11A C12A C13A C17A 173.1(3) . . . . ?
C7A C8A C14A C15A -62.3(4) . . . . ?
C9A C8A C14A C15A 176.0(3) . . . . ?
C7A C8A C14A C13A 177.2(3) . . . . ?
C9A C8A C14A C13A 55.5(3) . . . . ?
C12A C13A C14A C8A -63.9(3) . . . . ?
C22A C13A C14A C8A 57.2(4) . . . . ?
C17A C13A C14A C8A 171.6(3) . . . . ?
C12A C13A C14A C15A 168.6(3) . . . . ?
C22A C13A C14A C15A -70.4(3) . . . . ?
C17A C13A C14A C15A 44.0(3) . . . . ?
C8A C14A C15A C16A -156.8(3) . . . . ?
C13A C14A C15A C16A -31.7(3) . . . . ?
C14A C15A C16A C20A -109.9(3) . . . . ?
C14A C15A C16A C17A 6.2(3) . . . . ?
C12A C13A C17A C18A -42.0(4) . . . . ?
C22A C13A C17A C18A -167.5(3) . . . . ?
C14A C13A C17A C18A 74.4(3) . . . . ?
C12A C13A C17A C16A -156.7(3) . . . . ?
C22A C13A C17A C16A 77.8(3) . . . . ?
C14A C13A C17A C16A -40.3(3) . . . . ?
C12A C13A C17A Cl1A 79.2(3) . . . . ?
C22A C13A C17A Cl1A -46.3(3) . . . . ?
C14A C13A C17A Cl1A -164.3(2) . . . . ?
C20A C16A C17A C13A 142.7(3) . . . . ?
C15A C16A C17A C13A 21.4(3) . . . . ?
C20A C16A C17A C18A 20.2(3) . . . . ?
C15A C16A C17A C18A -101.1(3) . . . . ?
C20A C16A C17A Cl1A -92.9(3) . . . . ?
C15A C16A C17A Cl1A 145.8(2) . . . . ?
C13A C17A C18A O2A 65.3(4) . . . . ?
C16A C17A C18A O2A -179.2(3) . . . . ?
Cl1A C17A C18A O2A -60.5(4) . . . . ?
C13A C17A C18A C19A -116.4(3) . . . . ?
C16A C17A C18A C19A -0.9(4) . . . . ?
Cl1A C17A C18A C19A 117.8(3) . . . . ?
O2A C18A C19A C20A 159.4(4) . . . . ?
C17A C18A C19A C20A -18.8(4) . . . . ?
C18A C19A C20A C23A -91.4(3) . . . . ?
C18A C19A C20A C16A 30.8(4) . . . . ?
C15A C16A C20A C23A -152.2(3) . . . . ?
C17A C16A C20A C23A 92.9(3) . . . . ?
C15A C16A C20A C19A 83.3(3) . . . . ?
C17A C16A C20A C19A -31.7(3) . . . . ?
C19A C20A C23A C24A 8.5(5) . . . . ?
C16A C20A C23A C24A -109.3(4) . . . . ?
C19A C20A C23A C28A -170.8(3) . . . . ?
C16A C20A C23A C28A 71.5(4) . . . . ?
C28A C23A C24A C25A -0.2(5) . . . . ?
C20A C23A C24A C25A -179.5(3) . . . . ?
C23A C24A C25A C26A -0.1(6) . . . . ?
C24A C25A C26A F1A 179.6(3) . . . . ?
C24A C25A C26A C27A 0.4(6) . . . . ?
F1A C26A C27A C28A -179.6(3) . . . . ?
C25A C26A C27A C28A -0.4(6) . . . . ?
C26A C27A C28A C23A 0.0(5) . . . . ?
C24A C23A C28A C27A 0.3(5) . . . . ?
C20A C23A C28A C27A 179.6(3) . . . . ?
C10B C1B C2B C3B -54.4(4) . . . . ?
C1B C2B C3B O1B -155.2(3) . . . . ?
C1B C2B C3B C4B 28.1(4) . . . . ?
O1B C3B C4B C5B -173.5(3) . . . . ?
C2B C3B C4B C5B 3.2(5) . . . . ?
C3B C4B C5B C6B 166.7(3) . . . . ?
C3B C4B C5B C10B -8.8(5) . . . . ?
C4B C5B C6B C7B 135.0(3) . . . . ?
C10B C5B C6B C7B -49.3(4) . . . . ?
C5B C6B C7B C8B 52.3(4) . . . . ?
C6B C7B C8B C14B -178.0(2) . . . . ?
C6B C7B C8B C9B -57.7(3) . . . . ?
C7B C8B C9B C11B -172.3(3) . . . . ?
C14B C8B C9B C11B -50.8(3) . . . . ?
C7B C8B C9B C10B 59.8(3) . . . . ?
C14B C8B C9B C10B -178.6(2) . . . . ?
C4B C5B C10B C1B -17.3(4) . . . . ?
C6B C5B C10B C1B 167.1(3) . . . . ?
C4B C5B C10B C21B 102.3(3) . . . . ?
C6B C5B C10B C21B -73.3(3) . . . . ?
C4B C5B C10B C9B -135.8(3) . . . . ?
C6B C5B C10B C9B 48.6(3) . . . . ?
C2B C1B C10B C5B 48.0(4) . . . . ?
C2B C1B C10B C21B -70.7(3) . . . . ?
C2B C1B C10B C9B 166.4(3) . . . . ?
C11B C9B C10B C5B 178.9(2) . . . . ?
C8B C9B C10B C5B -53.4(3) . . . . ?
C11B C9B C10B C1B 59.7(3) . . . . ?
C8B C9B C10B C1B -172.6(2) . . . . ?
C11B C9B C10B C21B -61.7(3) . . . . ?
C8B C9B C10B C21B 66.1(3) . . . . ?
C8B C9B C11B C12B 52.1(3) . . . . ?
C10B C9B C11B C12B 179.8(2) . . . . ?
C9B C11B C12B C13B -54.7(3) . . . . ?
C11B C12B C13B C14B 56.3(3) . . . . ?
C11B C12B C13B C22B -66.8(3) . . . . ?
C11B C12B C13B C17B 167.3(2) . . . . ?
C7B C8B C14B C15B -61.2(3) . . . . ?
C9B C8B C14B C15B 178.3(3) . . . . ?
C7B C8B C14B C13B 176.7(2) . . . . ?
C9B C8B C14B C13B 56.2(3) . . . . ?
C12B C13B C14B C8B -59.7(3) . . . . ?
C22B C13B C14B C8B 61.6(3) . . . . ?
C17B C13B C14B C8B 176.4(2) . . . . ?
C12B C13B C14B C15B 170.8(2) . . . . ?
C22B C13B C14B C15B -67.9(3) . . . . ?
C17B C13B C14B C15B 46.9(3) . . . . ?
C8B C14B C15B C16B -160.7(3) . . . . ?
C13B C14B C15B C16B -33.4(3) . . . . ?
C14B C15B C16B C17B 5.6(3) . . . . ?
C14B C15B C16B C20B -109.2(3) . . . . ?
C12B C13B C17B C16B -160.6(2) . . . . ?
C14B C13B C17B C16B -43.8(3) . . . . ?
C22B C13B C17B C16B 73.4(3) . . . . ?
C12B C13B C17B C18B -46.9(3) . . . . ?
C14B C13B C17B C18B 69.9(3) . . . . ?
C22B C13B C17B C18B -172.9(2) . . . . ?
C12B C13B C17B Cl1B 74.3(3) . . . . ?
C14B C13B C17B Cl1B -168.89(19) . . . . ?
C22B C13B C17B Cl1B -51.7(3) . . . . ?
C20B C16B C17B C13B 143.4(2) . . . . ?
C15B C16B C17B C13B 24.1(3) . . . . ?
C20B C16B C17B C18B 22.7(3) . . . . ?
C15B C16B C17B C18B -96.6(3) . . . . ?
C20B C16B C17B Cl1B -91.2(3) . . . . ?
C15B C16B C17B Cl1B 149.5(2) . . . . ?
C13B C17B C18B O2B 61.1(4) . . . . ?
C16B C17B C18B O2B 175.9(3) . . . . ?
Cl1B C17B C18B O2B -64.7(3) . . . . ?
C13B C17B C18B C19B -117.7(3) . . . . ?
C16B C17B C18B C19B -2.9(3) . . . . ?
Cl1B C17B C18B C19B 116.5(2) . . . . ?
O2B C18B C19B C20B 162.9(3) . . . . ?
C17B C18B C19B C20B -18.3(3) . . . . ?
C18B C19B C20B C23B -91.7(3) . . . . ?
C18B C19B C20B C16B 31.6(3) . . . . ?
C17B C16B C20B C23B 90.6(3) . . . . ?
C15B C16B C20B C23B -156.3(2) . . . . ?
C17B C16B C20B C19B -33.8(3) . . . . ?
C15B C16B C20B C19B 79.3(3) . . . . ?
C19B C20B C23B C24B 15.9(4) . . . . ?
C16B C20B C23B C24B -101.5(4) . . . . ?
C19B C20B C23B C28B -162.7(3) . . . . ?
C16B C20B C23B C28B 79.8(3) . . . . ?
C28B C23B C24B C25B -0.1(5) . . . . ?
C20B C23B C24B C25B -178.8(3) . . . . ?
C23B C24B C25B C26B -0.3(6) . . . . ?
C24B C25B C26B F1B 179.4(3) . . . . ?
C24B C25B C26B C27B 0.0(6) . . . . ?
F1B C26B C27B C28B -178.6(3) . . . . ?
C25B C26B C27B C28B 0.8(6) . . . . ?
C26B C27B C28B C23B -1.3(5) . . . . ?
C24B C23B C28B C27B 1.0(5) . . . . ?
C20B C23B C28B C27B 179.7(3) . . . . ?

_refine_diff_density_max         1.402
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.080


