# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_d
_database_code_depnum_ccdc_archive 'CCDC 1975385'
loop_
_audit_author_name
_audit_author_address
'Xueliang Huang'
;Fujian Institute of Research on the Structure of Matter,  Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-01-04 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 O2'
_chemical_formula_weight         314.36

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.536(2)
_cell_length_b                   8.2902(17)
_cell_length_c                   18.320(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.28(3)
_cell_angle_gamma                90.00
_cell_volume                     1663.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    4150
_cell_measurement_theta_min      2.7175
_cell_measurement_theta_max      27.4700

_exptl_crystal_description       Prism
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10501
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2895
_reflns_number_gt                2214
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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     
'calc w=1/[σ²(Fo²)+(0.0736P)²+0.0067P] 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_number_reflns         2895
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.1149
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.004

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7878(2) 0.2825(3) 0.35521(12) 0.0792(6) Uani 1 1 d . . .
H1A H 0.7964 0.3924 0.3411 0.119 Uiso 1 1 calc R . .
H1B H 0.8014 0.2763 0.4096 0.119 Uiso 1 1 calc R . .
H1C H 0.7070 0.2451 0.3282 0.119 Uiso 1 1 calc R . .
O1 O 0.87512(13) 0.18431(16) 0.33550(7) 0.0676(4) Uani 1 1 d . . .
C2 C 0.87247(16) 0.1858(2) 0.26015(10) 0.0523(5) Uani 1 1 d . . .
O2 O 0.89724(9) 0.16957(13) 0.03946(6) 0.0467(3) Uani 1 1 d . . .
C3 C 0.79085(15) 0.27426(19) 0.20231(10) 0.0490(4) Uani 1 1 d . . .
H3 H 0.7328 0.3390 0.2136 0.059 Uiso 1 1 calc R . .
C4 C 0.79569(14) 0.26636(18) 0.12718(10) 0.0426(4) Uani 1 1 d . . .
C5 C 0.88335(14) 0.17022(18) 0.11131(9) 0.0420(4) Uani 1 1 d . . .
C6 C 0.96488(15) 0.0825(2) 0.16869(10) 0.0540(5) Uani 1 1 d . . .
H6 H 1.0231 0.0178 0.1576 0.065 Uiso 1 1 calc R . .
C7 C 0.95927(16) 0.0916(2) 0.24267(10) 0.0583(5) Uani 1 1 d . . .
H7 H 1.0149 0.0334 0.2816 0.070 Uiso 1 1 calc R . .
C8 C 0.71356(15) 0.35611(18) 0.06340(10) 0.0456(4) Uani 1 1 d . . .
H8 H 0.6640 0.4366 0.0730 0.055 Uiso 1 1 calc R . .
C9 C 0.70927(14) 0.32350(17) -0.00781(10) 0.0437(4) Uani 1 1 d . . .
H9 H 0.6561 0.3815 -0.0479 0.052 Uiso 1 1 calc R . .
C10 C 0.78843(14) 0.19441(18) -0.02615(9) 0.0412(4) Uani 1 1 d . . .
C11 C 0.83428(14) 0.25299(18) -0.09080(10) 0.0443(4) Uani 1 1 d . . .
C12 C 0.94172(17) 0.3387(2) -0.07545(12) 0.0578(5) Uani 1 1 d . . .
H12 H 0.9895 0.3550 -0.0247 0.069 Uiso 1 1 calc R . .
C13 C 0.9795(2) 0.4006(3) -0.13417(15) 0.0759(6) Uani 1 1 d . . .
H13 H 1.0521 0.4585 -0.1227 0.091 Uiso 1 1 calc R . .
C17 C 0.72213(14) 0.03214(17) -0.04579(9) 0.0409(4) Uani 1 1 d . . .
C18 C 0.59704(15) 0.0207(2) -0.06462(10) 0.0532(5) Uani 1 1 d . . .
H18 H 0.5512 0.1128 -0.0642 0.064 Uiso 1 1 calc R . .
C19 C 0.53885(17) -0.1265(2) -0.08414(11) 0.0619(5) Uani 1 1 d . . .
H19 H 0.4543 -0.1329 -0.0970 0.074 Uiso 1 1 calc R . .
C20 C 0.60585(19) -0.2628(2) -0.08444(12) 0.0620(5) Uani 1 1 d . . .
H20 H 0.5669 -0.3618 -0.0972 0.074 Uiso 1 1 calc R . .
C21 C 0.73021(19) -0.2529(2) -0.06594(12) 0.0612(5) Uani 1 1 d . . .
H21 H 0.7756 -0.3454 -0.0663 0.073 Uiso 1 1 calc R . .
C22 C 0.78849(16) -0.10615(19) -0.04677(10) 0.0521(5) Uani 1 1 d . . .
H22 H 0.8730 -0.1004 -0.0344 0.063 Uiso 1 1 calc R . .
C16 C 0.76609(19) 0.2307(3) -0.16660(11) 0.0665(6) Uani 1 1 d . . .
H16 H 0.6930 0.1740 -0.1784 0.080 Uiso 1 1 calc R . .
C15 C 0.8044(2) 0.2912(3) -0.22538(13) 0.0859(7) Uani 1 1 d . . .
H15 H 0.7579 0.2735 -0.2763 0.103 Uiso 1 1 calc R . .
C14 C 0.9108(2) 0.3772(3) -0.20885(15) 0.0838(7) Uani 1 1 d . . .
H14 H 0.9361 0.4195 -0.2484 0.101 Uiso 1 1 calc R . .


_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 O1 1.427(2) . ?
O1 C2 1.371(2) . ?
C2 C7 1.384(3) . ?
C2 C3 1.386(3) . ?
O2 C5 1.3749(19) . ?
O2 C10 1.4549(19) . ?
C3 C4 1.396(2) . ?
C4 C5 1.388(2) . ?
C4 C8 1.457(2) . ?
C5 C6 1.378(2) . ?
C6 C7 1.379(2) . ?
C8 C9 1.318(2) . ?
C9 C10 1.512(2) . ?
C10 C11 1.520(2) . ?
C10 C17 1.534(2) . ?
C11 C16 1.377(3) . ?
C11 C12 1.379(2) . ?
C12 C13 1.380(3) . ?
C13 C14 1.363(3) . ?
C17 C18 1.378(2) . ?
C17 C22 1.382(2) . ?
C18 C19 1.385(2) . ?
C19 C20 1.370(3) . ?
C20 C21 1.369(3) . ?
C21 C22 1.381(2) . ?
C16 C15 1.380(3) . ?
C15 C14 1.369(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 O1 C1 117.07(16) . . ?
O1 C2 C7 116.01(16) . . ?
O1 C2 C3 124.72(17) . . ?
C7 C2 C3 119.27(17) . . ?
C5 O2 C10 117.46(12) . . ?
C2 C3 C4 120.07(16) . . ?
C5 C4 C3 119.37(15) . . ?
C5 C4 C8 117.28(15) . . ?
C3 C4 C8 123.34(15) . . ?
O2 C5 C6 118.15(14) . . ?
O2 C5 C4 120.94(14) . . ?
C6 C5 C4 120.72(16) . . ?
C5 C6 C7 119.33(17) . . ?
C6 C7 C2 121.23(16) . . ?
C9 C8 C4 120.15(15) . . ?
C8 C9 C10 121.84(14) . . ?
O2 C10 C9 109.96(13) . . ?
O2 C10 C11 105.55(12) . . ?
C9 C10 C11 109.22(12) . . ?
O2 C10 C17 107.90(12) . . ?
C9 C10 C17 112.44(13) . . ?
C11 C10 C17 111.55(13) . . ?
C16 C11 C12 117.87(17) . . ?
C16 C11 C10 120.96(15) . . ?
C12 C11 C10 121.05(16) . . ?
C11 C12 C13 121.07(19) . . ?
C14 C13 C12 120.2(2) . . ?
C18 C17 C22 118.73(15) . . ?
C18 C17 C10 121.69(14) . . ?
C22 C17 C10 119.56(14) . . ?
C17 C18 C19 120.68(16) . . ?
C20 C19 C18 119.96(17) . . ?
C21 C20 C19 119.91(16) . . ?
C20 C21 C22 120.27(17) . . ?
C21 C22 C17 120.44(16) . . ?
C11 C16 C15 121.1(2) . . ?
C14 C15 C16 120.1(2) . . ?
C13 C14 C15 119.7(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
C1 O1 C2 C7 178.98(17) . . . . ?
C1 O1 C2 C3 -0.6(3) . . . . ?
O1 C2 C3 C4 -179.65(14) . . . . ?
C7 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C2 C3 C4 C8 -179.73(14) . . . . ?
C10 O2 C5 C6 152.38(14) . . . . ?
C10 O2 C5 C4 -32.54(19) . . . . ?
C3 C4 C5 O2 -174.69(13) . . . . ?
C8 C4 C5 O2 4.6(2) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C8 C4 C5 C6 179.56(14) . . . . ?
O2 C5 C6 C7 174.71(15) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C5 C6 C7 C2 0.7(3) . . . . ?
O1 C2 C7 C6 179.48(16) . . . . ?
C3 C2 C7 C6 -0.9(3) . . . . ?
C5 C4 C8 C9 12.0(2) . . . . ?
C3 C4 C8 C9 -168.76(15) . . . . ?
C4 C8 C9 C10 -0.3(2) . . . . ?
C5 O2 C10 C9 40.64(17) . . . . ?
C5 O2 C10 C11 158.32(12) . . . . ?
C5 O2 C10 C17 -82.31(15) . . . . ?
C8 C9 C10 O2 -25.0(2) . . . . ?
C8 C9 C10 C11 -140.36(15) . . . . ?
C8 C9 C10 C17 95.26(18) . . . . ?
O2 C10 C11 C16 154.95(16) . . . . ?
C9 C10 C11 C16 -86.88(19) . . . . ?
C17 C10 C11 C16 38.0(2) . . . . ?
O2 C10 C11 C12 -29.1(2) . . . . ?
C9 C10 C11 C12 89.09(18) . . . . ?
C17 C10 C11 C12 -146.01(15) . . . . ?
C16 C11 C12 C13 0.2(3) . . . . ?
C10 C11 C12 C13 -175.89(17) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
O2 C10 C17 C18 137.83(15) . . . . ?
C9 C10 C17 C18 16.4(2) . . . . ?
C11 C10 C17 C18 -106.68(18) . . . . ?
O2 C10 C17 C22 -43.91(19) . . . . ?
C9 C10 C17 C22 -165.34(15) . . . . ?
C11 C10 C17 C22 71.58(18) . . . . ?
C22 C17 C18 C19 0.0(3) . . . . ?
C10 C17 C18 C19 178.27(16) . . . . ?
C17 C18 C19 C20 0.4(3) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C19 C20 C21 C22 0.2(3) . . . . ?
C20 C21 C22 C17 0.2(3) . . . . ?
C18 C17 C22 C21 -0.3(3) . . . . ?
C10 C17 C22 C21 -178.59(16) . . . . ?
C12 C11 C16 C15 0.5(3) . . . . ?
C10 C11 C16 C15 176.54(19) . . . . ?
C11 C16 C15 C14 -1.1(4) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C16 C15 C14 C13 1.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1978345'
loop_
_audit_author_name
_audit_author_address
'Xueliang Huang'
;Fujian Institute of Research on the Structure of Matter,  Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-01-17 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16.50 Br2 O2.25'
_chemical_formula_weight         464.66

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      tetragonal
_space_group_IT_number           85
_space_group_name_H-M_alt        'P 4/n'
_space_group_name_Hall           '-P 4a'

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

_cell_length_a                   20.474(5)
_cell_length_b                   20.474(5)
_cell_length_c                   9.720(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4074(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11021
_cell_measurement_theta_min      2.8141
_cell_measurement_theta_max      27.4006

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_F_000             1844
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    3.991
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6563
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            32853
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.814
_diffrn_reflns_theta_max         27.399
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4639
_reflns_number_gt                3525
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1169P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4639
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0651
_refine_ls_wR_factor_ref         0.2140
_refine_ls_wR_factor_gt          0.1948
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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
Br1 Br 0.41447(2) 0.16080(2) 0.59933(6) 0.0734(2) Uani 1 1 d . . . . .
Br2 Br 0.39251(5) 0.44949(5) 0.00840(9) 0.1316(4) Uani 1 1 d . . . . .
O1 O 0.50892(13) 0.33851(12) 0.5286(3) 0.0557(6) Uani 1 1 d . . . . .
O2 O 0.34254(13) 0.25890(14) 0.3768(4) 0.0706(9) Uani 1 1 d . . . . .
H1 H 0.325979 0.219942 0.399598 0.085 Uiso 1 1 d R U . . .
O3 O 0.250000 0.250000 0.0422(15) 0.112(6) Uani 0.5 4 d S T P . .
O4 O 0.250000 0.250000 -0.2622(19) 0.129(7) Uani 0.5 4 d S T P . .
C1 C 0.50827(18) 0.26783(18) 0.5506(4) 0.0513(8) Uani 1 1 d . . . . .
C2 C 0.43608(18) 0.24915(19) 0.5319(4) 0.0535(9) Uani 1 1 d . . . . .
H2 H 0.410891 0.279707 0.588499 0.064 Uiso 1 1 calc R U . . .
C3 C 0.41229(18) 0.25819(19) 0.3854(5) 0.0555(9) Uani 1 1 d . . . . .
H3 H 0.429925 0.223546 0.326593 0.067 Uiso 1 1 calc R U . . .
C4 C 0.43592(18) 0.32451(19) 0.3351(4) 0.0546(9) Uani 1 1 d . . . . .
C5 C 0.4093(2) 0.3512(2) 0.2136(5) 0.0683(11) Uani 1 1 d . . . . .
H5 H 0.378456 0.328098 0.162902 0.082 Uiso 1 1 calc R U . . .
C6 C 0.4300(3) 0.4133(3) 0.1704(6) 0.0818(14) Uani 1 1 d . . . . .
C7 C 0.4762(3) 0.4478(2) 0.2422(7) 0.0835(15) Uani 1 1 d . . . . .
H7 H 0.489500 0.488687 0.211361 0.100 Uiso 1 1 calc R U . . .
C8 C 0.5029(2) 0.4216(2) 0.3601(6) 0.0672(11) Uani 1 1 d . . . . .
H8 H 0.534216 0.444712 0.409531 0.081 Uiso 1 1 calc R U . . .
C9 C 0.48249(18) 0.35973(19) 0.4049(4) 0.0535(9) Uani 1 1 d . . . . .
C10 C 0.55675(18) 0.23702(19) 0.4500(4) 0.0530(8) Uani 1 1 d . . . . .
C11 C 0.5489(2) 0.1764(2) 0.3903(5) 0.0615(10) Uani 1 1 d . . . . .
H11 H 0.511667 0.151947 0.408579 0.074 Uiso 1 1 calc R U . . .
C12 C 0.5977(3) 0.1515(2) 0.3010(6) 0.0762(13) Uani 1 1 d . . . . .
H12 H 0.592225 0.110456 0.261524 0.091 Uiso 1 1 calc R U . . .
C13 C 0.6516(2) 0.1862(3) 0.2728(5) 0.0782(14) Uani 1 1 d . . . . .
H13 H 0.683472 0.168872 0.215297 0.094 Uiso 1 1 calc R U . . .
C14 C 0.6597(2) 0.2473(3) 0.3287(5) 0.0756(13) Uani 1 1 d . . . . .
H14 H 0.696382 0.271971 0.306764 0.091 Uiso 1 1 calc R U . . .
C15 C 0.6126(2) 0.2723(2) 0.4187(5) 0.0630(10) Uani 1 1 d . . . . .
H15 H 0.618833 0.313255 0.458027 0.076 Uiso 1 1 calc R U . . .
C16 C 0.52936(19) 0.2607(2) 0.7023(4) 0.0577(9) Uani 1 1 d . . . . .
C17 C 0.5080(2) 0.3054(3) 0.7989(5) 0.0734(12) Uani 1 1 d . . . . .
H17 H 0.481171 0.339619 0.771068 0.088 Uiso 1 1 calc R U . . .
C18 C 0.5254(3) 0.3007(4) 0.9345(6) 0.0985(18) Uani 1 1 d . . . . .
H18 H 0.510788 0.331726 0.997209 0.118 Uiso 1 1 calc R U . . .
C19 C 0.5647(4) 0.2500(4) 0.9783(7) 0.105(2) Uani 1 1 d . . . . .
H19 H 0.576955 0.246850 1.070130 0.126 Uiso 1 1 calc R U . . .
C20 C 0.5857(3) 0.2036(4) 0.8829(7) 0.0968(19) Uani 1 1 d . . . . .
H20 H 0.611471 0.168798 0.911961 0.116 Uiso 1 1 calc R U . . .
C21 C 0.5685(2) 0.2088(2) 0.7437(5) 0.0717(12) Uani 1 1 d . . . . .
H21 H 0.583001 0.178112 0.680186 0.086 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 C2 1.974(4) . ?
Br2 C6 1.902(5) . ?
O1 C9 1.388(5) . ?
O1 C1 1.463(4) . ?
O2 C3 1.431(4) . ?
C1 C10 1.530(6) . ?
C1 C2 1.537(5) . ?
C1 C16 1.543(6) . ?
C2 C3 1.516(6) . ?
C3 C4 1.522(6) . ?
C4 C9 1.374(6) . ?
C4 C5 1.411(6) . ?
C5 C6 1.403(7) . ?
C6 C7 1.371(8) . ?
C7 C8 1.379(7) . ?
C8 C9 1.403(6) . ?
C10 C11 1.379(6) . ?
C10 C15 1.387(6) . ?
C11 C12 1.418(6) . ?
C12 C13 1.340(7) . ?
C13 C14 1.375(8) . ?
C14 C15 1.399(6) . ?
C16 C17 1.384(6) . ?
C16 C21 1.389(6) . ?
C17 C18 1.368(7) . ?
C18 C19 1.380(11) . ?
C19 C20 1.396(10) . ?
C20 C21 1.402(8) . ?

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
C9 O1 C1 115.7(3) . . ?
O1 C1 C10 107.9(3) . . ?
O1 C1 C2 103.7(3) . . ?
C10 C1 C2 116.4(3) . . ?
O1 C1 C16 103.4(3) . . ?
C10 C1 C16 113.0(3) . . ?
C2 C1 C16 111.0(3) . . ?
C3 C2 C1 113.0(3) . . ?
C3 C2 Br1 110.6(3) . . ?
C1 C2 Br1 113.8(3) . . ?
O2 C3 C2 112.2(4) . . ?
O2 C3 C4 106.8(3) . . ?
C2 C3 C4 108.0(3) . . ?
C9 C4 C5 118.5(4) . . ?
C9 C4 C3 122.0(4) . . ?
C5 C4 C3 119.5(4) . . ?
C6 C5 C4 119.0(5) . . ?
C7 C6 C5 121.5(5) . . ?
C7 C6 Br2 119.9(4) . . ?
C5 C6 Br2 118.6(4) . . ?
C6 C7 C8 119.8(5) . . ?
C7 C8 C9 119.4(5) . . ?
C4 C9 O1 122.3(3) . . ?
C4 C9 C8 121.8(4) . . ?
O1 C9 C8 115.8(4) . . ?
C11 C10 C15 118.2(4) . . ?
C11 C10 C1 124.4(4) . . ?
C15 C10 C1 117.4(4) . . ?
C10 C11 C12 120.0(4) . . ?
C13 C12 C11 120.9(5) . . ?
C12 C13 C14 120.1(4) . . ?
C13 C14 C15 119.8(5) . . ?
C10 C15 C14 121.0(5) . . ?
C17 C16 C21 119.4(4) . . ?
C17 C16 C1 119.8(4) . . ?
C21 C16 C1 120.7(4) . . ?
C18 C17 C16 121.6(6) . . ?
C17 C18 C19 120.1(7) . . ?
C18 C19 C20 119.2(6) . . ?
C19 C20 C21 120.7(6) . . ?
C16 C21 C20 118.9(6) . . ?

_refine_diff_density_max         0.955
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1978346'
loop_
_audit_author_name
_audit_author_address
'Xueliang Huang'
;Fujian Institute of Research on the Structure of Matter,  Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-01-17 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H24 O2 S'
_chemical_formula_weight         424.53

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   9.990(4)
_cell_length_b                   10.558(4)
_cell_length_c                   21.868(9)
_cell_angle_alpha                78.978(12)
_cell_angle_beta                 77.060(10)
_cell_angle_gamma                85.471(13)
_cell_volume                     2205.0(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6350
_cell_measurement_theta_min      2.9350
_cell_measurement_theta_max      27.5126

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.169
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9235
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            29070
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.914
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             10051
_reflns_number_gt                8456
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0501P)²+0.3846P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10051
_refine_ls_number_parameters     561
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1295
_refine_ls_wR_factor_gt          0.1213
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

_vrf_PLAT420_6                   
;
PROBLEM: D-H Without Acceptor       O4       --H4       .     Please Check 
RESPONSE: We have carefully checked the crystal structure. There is no suitable 
acceptor close to the OH hydrogen atoms.
;

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
S1 S 0.52422(5) 0.18762(5) 0.74261(2) 0.04652(13) Uani 1 1 d . . . . .
S2 S 0.82564(5) 0.95476(5) 0.88299(2) 0.04844(14) Uani 1 1 d . . . . .
O1 O 0.42683(12) 0.33846(11) 0.57148(5) 0.0395(3) Uani 1 1 d . . . . .
O2 O 0.37117(16) -0.00805(13) 0.69417(6) 0.0587(4) Uani 1 1 d . . . . .
H1 H 0.397833 -0.016452 0.729058 0.070 Uiso 1 1 d R U . . .
O3 O 0.53673(12) 0.80976(12) 0.81340(5) 0.0396(3) Uani 1 1 d . . . . .
O4 O 0.51986(14) 1.07476(13) 0.92486(6) 0.0522(3) Uani 1 1 d . . . . .
H4 H 0.479212 1.109164 0.895184 0.063 Uiso 1 1 d R U . . .
C1 C 0.52088(17) 0.31674(16) 0.61472(7) 0.0347(4) Uani 1 1 d . . . . .
C2 C 0.45525(18) 0.21046(16) 0.67025(7) 0.0364(4) Uani 1 1 d . . . . .
H2 H 0.358610 0.238128 0.682813 0.044 Uiso 1 1 calc R U . . .
C3 C 0.45410(19) 0.08275(17) 0.64745(8) 0.0417(4) Uani 1 1 d . . . . .
H3 H 0.548347 0.046770 0.637856 0.050 Uiso 1 1 calc R U . . .
C4 C 0.39723(18) 0.10687(17) 0.58777(8) 0.0405(4) Uani 1 1 d . . . . .
C5 C 0.3518(2) 0.0060(2) 0.56586(10) 0.0526(5) Uani 1 1 d . . . . .
H5 H 0.355123 -0.077561 0.588854 0.063 Uiso 1 1 calc R U . . .
C6 C 0.3022(2) 0.0277(2) 0.51085(11) 0.0604(6) Uani 1 1 d . . . . .
H6 H 0.271532 -0.040627 0.497033 0.072 Uiso 1 1 calc R U . . .
C7 C 0.2982(2) 0.1507(2) 0.47635(10) 0.0583(5) Uani 1 1 d . . . . .
H7 H 0.266032 0.165072 0.438769 0.070 Uiso 1 1 calc R U . . .
C8 C 0.3415(2) 0.2531(2) 0.49685(9) 0.0495(5) Uani 1 1 d . . . . .
H8 H 0.338102 0.336299 0.473506 0.059 Uiso 1 1 calc R U . . .
C9 C 0.39019(18) 0.23028(17) 0.55285(8) 0.0388(4) Uani 1 1 d . . . . .
C10 C 0.66377(18) 0.28560(16) 0.57675(8) 0.0383(4) Uani 1 1 d . . . . .
C11 C 0.7001(2) 0.3464(2) 0.51358(9) 0.0515(5) Uani 1 1 d . . . . .
H11 H 0.634787 0.397524 0.494868 0.062 Uiso 1 1 calc R U . . .
C12 C 0.8310(2) 0.3324(2) 0.47808(11) 0.0667(6) Uani 1 1 d . . . . .
H12 H 0.853076 0.373295 0.435692 0.080 Uiso 1 1 calc R U . . .
C13 C 0.9292(2) 0.2581(3) 0.50508(12) 0.0689(6) Uani 1 1 d . . . . .
H13 H 1.017828 0.249036 0.481200 0.083 Uiso 1 1 calc R U . . .
C14 C 0.8956(2) 0.1974(2) 0.56743(11) 0.0593(5) Uani 1 1 d . . . . .
H14 H 0.961818 0.146764 0.585797 0.071 Uiso 1 1 calc R U . . .
C15 C 0.76407(19) 0.21076(19) 0.60327(9) 0.0477(4) Uani 1 1 d . . . . .
H15 H 0.742635 0.169182 0.645566 0.057 Uiso 1 1 calc R U . . .
C16 C 0.52015(17) 0.44511(16) 0.63745(7) 0.0358(4) Uani 1 1 d . . . . .
C17 C 0.63429(19) 0.48069(18) 0.65565(9) 0.0448(4) Uani 1 1 d . . . . .
H17 H 0.713054 0.427051 0.652817 0.054 Uiso 1 1 calc R U . . .
C18 C 0.6320(2) 0.5952(2) 0.67796(10) 0.0524(5) Uani 1 1 d . . . . .
H18 H 0.708921 0.617514 0.690352 0.063 Uiso 1 1 calc R U . . .
C19 C 0.5174(2) 0.6758(2) 0.68189(10) 0.0541(5) Uani 1 1 d . . . . .
H19 H 0.516154 0.752953 0.696673 0.065 Uiso 1 1 calc R U . . .
C20 C 0.4043(2) 0.64173(19) 0.66381(10) 0.0533(5) Uani 1 1 d . . . . .
H20 H 0.326336 0.696420 0.666204 0.064 Uiso 1 1 calc R U . . .
C21 C 0.40479(19) 0.52691(18) 0.64203(9) 0.0439(4) Uani 1 1 d . . . . .
H21 H 0.326939 0.504670 0.630406 0.053 Uiso 1 1 calc R U . . .
C22 C 0.38358(19) 0.25066(18) 0.79548(8) 0.0421(4) Uani 1 1 d . . . . .
C23 C 0.3835(3) 0.3750(2) 0.80576(10) 0.0671(7) Uani 1 1 d . . . . .
H23 H 0.458519 0.425730 0.786012 0.081 Uiso 1 1 calc R U . . .
C24 C 0.2725(3) 0.4252(2) 0.84529(11) 0.0772(8) Uani 1 1 d . . . . .
H24 H 0.274025 0.509707 0.851504 0.093 Uiso 1 1 calc R U . . .
C25 C 0.1600(2) 0.3535(2) 0.87560(10) 0.0585(5) Uani 1 1 d . . . . .
C26 C 0.1620(2) 0.2282(2) 0.86599(10) 0.0577(5) Uani 1 1 d . . . . .
H26 H 0.087815 0.177098 0.886672 0.069 Uiso 1 1 calc R U . . .
C27 C 0.2716(2) 0.17672(19) 0.82632(9) 0.0501(5) Uani 1 1 d . . . . .
H27 H 0.270052 0.092032 0.820320 0.060 Uiso 1 1 calc R U . . .
C28 C 0.0366(3) 0.4098(3) 0.91734(14) 0.0929(9) Uani 1 1 d . . . . .
H28A H 0.050071 0.499247 0.916311 0.139 Uiso 1 1 calc R U . . .
H28B H 0.025796 0.363724 0.960373 0.139 Uiso 1 1 calc R U . . .
H28C H -0.044446 0.402057 0.901780 0.139 Uiso 1 1 calc R U . . .
C29 C 0.66113(17) 0.79821(17) 0.83893(8) 0.0368(4) Uani 1 1 d . . . . .
C30 C 0.66321(16) 0.92558(17) 0.86375(8) 0.0361(4) Uani 1 1 d . . . . .
H30 H 0.651159 0.994928 0.828372 0.043 Uiso 1 1 calc R U . . .
C31 C 0.54076(18) 0.94159(18) 0.91851(8) 0.0405(4) Uani 1 1 d . . . . .
H31 H 0.561925 0.892087 0.958143 0.049 Uiso 1 1 calc R U . . .
C32 C 0.41277(17) 0.88945(17) 0.90803(8) 0.0388(4) Uani 1 1 d . . . . .
C33 C 0.2862(2) 0.9054(2) 0.94883(9) 0.0511(5) Uani 1 1 d . . . . .
H33 H 0.281946 0.942892 0.984430 0.061 Uiso 1 1 calc R U . . .
C34 C 0.1669(2) 0.8663(2) 0.93720(11) 0.0584(6) Uani 1 1 d . . . . .
H34 H 0.083050 0.877481 0.964810 0.070 Uiso 1 1 calc R U . . .
C35 C 0.1726(2) 0.8107(2) 0.88446(12) 0.0589(6) Uani 1 1 d . . . . .
H35 H 0.092159 0.785831 0.876126 0.071 Uiso 1 1 calc R U . . .
C36 C 0.29739(19) 0.79165(19) 0.84387(10) 0.0496(5) Uani 1 1 d . . . . .
H36 H 0.301322 0.753175 0.808603 0.060 Uiso 1 1 calc R U . . .
C37 C 0.41632(17) 0.83046(16) 0.85628(8) 0.0383(4) Uani 1 1 d . . . . .
C38 C 0.65602(18) 0.67353(18) 0.88798(9) 0.0442(4) Uani 1 1 d . . . . .
C39 C 0.7034(2) 0.6613(2) 0.94390(9) 0.0576(5) Uani 1 1 d . . . . .
H39 H 0.735127 0.732874 0.954603 0.069 Uiso 1 1 calc R U . . .
C40 C 0.7035(2) 0.5423(3) 0.98376(12) 0.0771(8) Uani 1 1 d . . . . .
H40 H 0.735474 0.534604 1.021165 0.093 Uiso 1 1 calc R U . . .
C41 C 0.6573(3) 0.4361(3) 0.96880(15) 0.0854(10) Uani 1 1 d . . . . .
H41 H 0.658130 0.356643 0.995855 0.102 Uiso 1 1 calc R U . . .
C42 C 0.6098(3) 0.4468(2) 0.91405(14) 0.0756(8) Uani 1 1 d . . . . .
H42 H 0.577395 0.374714 0.904069 0.091 Uiso 1 1 calc R U . . .
C43 C 0.6098(2) 0.5649(2) 0.87329(11) 0.0582(5) Uani 1 1 d . . . . .
H43 H 0.578625 0.571234 0.835778 0.070 Uiso 1 1 calc R U . . .
C44 C 0.77879(17) 0.79192(17) 0.78122(8) 0.0381(4) Uani 1 1 d . . . . .
C45 C 0.8951(2) 0.7130(2) 0.78631(10) 0.0532(5) Uani 1 1 d . . . . .
H45 H 0.899956 0.659366 0.824859 0.064 Uiso 1 1 calc R U . . .
C46 C 1.0041(2) 0.7135(2) 0.73431(11) 0.0664(6) Uani 1 1 d . . . . .
H46 H 1.081998 0.661032 0.738408 0.080 Uiso 1 1 calc R U . . .
C47 C 0.9980(2) 0.7906(2) 0.67700(11) 0.0644(6) Uani 1 1 d . . . . .
H47 H 1.071551 0.790759 0.642323 0.077 Uiso 1 1 calc R U . . .
C48 C 0.8827(2) 0.8678(2) 0.67099(9) 0.0559(5) Uani 1 1 d . . . . .
H48 H 0.877569 0.919313 0.631948 0.067 Uiso 1 1 calc R U . . .
C49 C 0.7739(2) 0.86920(18) 0.72301(8) 0.0451(4) Uani 1 1 d . . . . .
H49 H 0.696741 0.922674 0.718671 0.054 Uiso 1 1 calc R U . . .
C50 C 0.88723(18) 1.0825(2) 0.81967(9) 0.0467(4) Uani 1 1 d . . . . .
C51 C 0.9923(2) 1.0600(2) 0.76927(10) 0.0524(5) Uani 1 1 d . . . . .
H51 H 1.031425 0.977266 0.768397 0.063 Uiso 1 1 calc R U . . .
C52 C 1.0390(2) 1.1602(2) 0.72030(11) 0.0608(6) Uani 1 1 d . . . . .
H52 H 1.109743 1.143629 0.686767 0.073 Uiso 1 1 calc R U . . .
C53 C 0.9838(2) 1.2841(2) 0.71974(12) 0.0652(6) Uani 1 1 d . . . . .
C54 C 0.8797(2) 1.3060(2) 0.77039(14) 0.0715(7) Uani 1 1 d . . . . .
H54 H 0.841222 1.388921 0.771152 0.086 Uiso 1 1 calc R U . . .
C55 C 0.8317(2) 1.2072(2) 0.81997(12) 0.0620(6) Uani 1 1 d . . . . .
H55 H 0.761841 1.224287 0.853715 0.074 Uiso 1 1 calc R U . . .
C56 C 1.0355(3) 1.3921(3) 0.66551(16) 0.0960(10) Uani 1 1 d . . . . .
H56A H 1.117445 1.362882 0.638775 0.144 Uiso 1 1 calc R U . . .
H56B H 1.055668 1.464299 0.682344 0.144 Uiso 1 1 calc R U . . .
H56C H 0.966387 1.417912 0.640899 0.144 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
S1 C22 1.7812(19) . ?
S1 C2 1.8311(18) . ?
S2 C50 1.775(2) . ?
S2 C30 1.8274(18) . ?
O1 C9 1.384(2) . ?
O1 C1 1.4527(19) . ?
O2 C3 1.422(2) . ?
O3 C37 1.381(2) . ?
O3 C29 1.460(2) . ?
O4 C31 1.434(2) . ?
C1 C10 1.528(2) . ?
C1 C16 1.529(2) . ?
C1 C2 1.550(2) . ?
C2 C3 1.526(2) . ?
C3 C4 1.508(3) . ?
C4 C9 1.384(3) . ?
C4 C5 1.393(3) . ?
C5 C6 1.374(3) . ?
C6 C7 1.375(3) . ?
C7 C8 1.379(3) . ?
C8 C9 1.389(2) . ?
C10 C11 1.388(2) . ?
C10 C15 1.387(3) . ?
C11 C12 1.376(3) . ?
C12 C13 1.373(3) . ?
C13 C14 1.370(3) . ?
C14 C15 1.383(3) . ?
C16 C21 1.382(2) . ?
C16 C17 1.388(2) . ?
C17 C18 1.385(3) . ?
C18 C19 1.369(3) . ?
C19 C20 1.372(3) . ?
C20 C21 1.384(3) . ?
C22 C23 1.374(3) . ?
C22 C27 1.384(3) . ?
C23 C24 1.382(3) . ?
C24 C25 1.372(3) . ?
C25 C26 1.376(3) . ?
C25 C28 1.515(3) . ?
C26 C27 1.381(3) . ?
C29 C38 1.527(2) . ?
C29 C44 1.528(2) . ?
C29 C30 1.547(2) . ?
C30 C31 1.532(2) . ?
C31 C32 1.510(3) . ?
C32 C37 1.385(3) . ?
C32 C33 1.394(2) . ?
C33 C34 1.382(3) . ?
C34 C35 1.379(3) . ?
C35 C36 1.384(3) . ?
C36 C37 1.385(3) . ?
C38 C43 1.387(3) . ?
C38 C39 1.388(3) . ?
C39 C40 1.385(3) . ?
C40 C41 1.367(4) . ?
C41 C42 1.366(4) . ?
C42 C43 1.387(3) . ?
C44 C49 1.383(2) . ?
C44 C45 1.388(3) . ?
C45 C46 1.387(3) . ?
C46 C47 1.369(3) . ?
C47 C48 1.374(3) . ?
C48 C49 1.388(3) . ?
C50 C51 1.384(3) . ?
C50 C55 1.388(3) . ?
C51 C52 1.380(3) . ?
C52 C53 1.378(3) . ?
C53 C54 1.380(3) . ?
C53 C56 1.509(3) . ?
C54 C55 1.381(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
C22 S1 C2 100.47(9) . . ?
C50 S2 C30 100.68(8) . . ?
C9 O1 C1 116.50(13) . . ?
C37 O3 C29 115.03(13) . . ?
O1 C1 C10 108.00(13) . . ?
O1 C1 C16 105.12(13) . . ?
C10 C1 C16 110.07(14) . . ?
O1 C1 C2 104.90(13) . . ?
C10 C1 C2 116.94(14) . . ?
C16 C1 C2 110.99(13) . . ?
C3 C2 C1 111.06(13) . . ?
C3 C2 S1 111.21(12) . . ?
C1 C2 S1 116.16(12) . . ?
O2 C3 C4 108.48(15) . . ?
O2 C3 C2 111.63(14) . . ?
C4 C3 C2 109.10(14) . . ?
C9 C4 C5 118.17(17) . . ?
C9 C4 C3 120.66(16) . . ?
C5 C4 C3 121.16(17) . . ?
C6 C5 C4 121.2(2) . . ?
C5 C6 C7 119.7(2) . . ?
C6 C7 C8 120.7(2) . . ?
C7 C8 C9 119.1(2) . . ?
O1 C9 C4 123.19(15) . . ?
O1 C9 C8 115.64(16) . . ?
C4 C9 C8 121.15(17) . . ?
C11 C10 C15 117.84(17) . . ?
C11 C10 C1 117.94(16) . . ?
C15 C10 C1 123.88(15) . . ?
C12 C11 C10 121.27(19) . . ?
C13 C12 C11 120.2(2) . . ?
C14 C13 C12 119.6(2) . . ?
C13 C14 C15 120.5(2) . . ?
C14 C15 C10 120.66(18) . . ?
C21 C16 C17 118.34(17) . . ?
C21 C16 C1 120.89(16) . . ?
C17 C16 C1 120.75(15) . . ?
C18 C17 C16 120.67(18) . . ?
C19 C18 C17 120.42(19) . . ?
C18 C19 C20 119.33(19) . . ?
C19 C20 C21 120.79(19) . . ?
C16 C21 C20 120.45(18) . . ?
C23 C22 C27 118.57(19) . . ?
C23 C22 S1 120.37(15) . . ?
C27 C22 S1 121.06(15) . . ?
C22 C23 C24 120.3(2) . . ?
C25 C24 C23 121.7(2) . . ?
C24 C25 C26 117.6(2) . . ?
C24 C25 C28 121.7(2) . . ?
C26 C25 C28 120.7(2) . . ?
C25 C26 C27 121.5(2) . . ?
C26 C27 C22 120.25(19) . . ?
O3 C29 C38 108.13(14) . . ?
O3 C29 C44 104.65(13) . . ?
C38 C29 C44 111.30(14) . . ?
O3 C29 C30 104.92(13) . . ?
C38 C29 C30 116.63(14) . . ?
C44 C29 C30 110.30(14) . . ?
C31 C30 C29 112.44(14) . . ?
C31 C30 S2 111.66(12) . . ?
C29 C30 S2 114.87(11) . . ?
O4 C31 C32 111.03(14) . . ?
O4 C31 C30 110.05(14) . . ?
C32 C31 C30 110.73(14) . . ?
C37 C32 C33 118.19(17) . . ?
C37 C32 C31 121.31(15) . . ?
C33 C32 C31 120.42(17) . . ?
C34 C33 C32 121.0(2) . . ?
C35 C34 C33 119.73(19) . . ?
C34 C35 C36 120.4(2) . . ?
C35 C36 C37 119.3(2) . . ?
O3 C37 C36 116.14(16) . . ?
O3 C37 C32 122.49(15) . . ?
C36 C37 C32 121.35(17) . . ?
C43 C38 C39 118.63(19) . . ?
C43 C38 C29 117.57(18) . . ?
C39 C38 C29 123.65(19) . . ?
C40 C39 C38 119.9(2) . . ?
C41 C40 C39 120.8(3) . . ?
C42 C41 C40 119.9(2) . . ?
C41 C42 C43 120.1(3) . . ?
C38 C43 C42 120.6(2) . . ?
C49 C44 C45 118.40(17) . . ?
C49 C44 C29 120.38(16) . . ?
C45 C44 C29 121.17(16) . . ?
C46 C45 C44 120.4(2) . . ?
C47 C46 C45 120.6(2) . . ?
C46 C47 C48 119.63(19) . . ?
C47 C48 C49 120.2(2) . . ?
C44 C49 C48 120.74(19) . . ?
C51 C50 C55 118.7(2) . . ?
C51 C50 S2 120.64(16) . . ?
C55 C50 S2 120.66(16) . . ?
C52 C51 C50 120.0(2) . . ?
C53 C52 C51 121.8(2) . . ?
C52 C53 C54 117.8(2) . . ?
C52 C53 C56 121.0(2) . . ?
C54 C53 C56 121.2(2) . . ?
C53 C54 C55 121.3(2) . . ?
C54 C55 C50 120.3(2) . . ?

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1975387'
loop_
_audit_author_name
_audit_author_address
'Xueliang Huang'
;Fujian Institute of Research on the Structure of Matter,  Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-01-04 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H17 Br O'
_chemical_formula_weight         413.30

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.940(3)
_cell_length_b                   10.721(2)
_cell_length_c                   10.610(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.81(3)
_cell_angle_gamma                90.00
_cell_volume                     1886.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    5135
_cell_measurement_theta_min      3.1009
_cell_measurement_theta_max      27.4662

_exptl_crystal_description       Prism
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    2.191
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15300
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4305
_reflns_number_gt                2699
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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     
'calc w=1/[σ²(Fo²)+(0.0457P)²+0.0000P] 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_number_reflns         4305
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0952
_refine_ls_wR_factor_gt          0.0855
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_restrained_S_all      0.933
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.008963(17) 0.99444(2) 0.32273(2) 0.07234(13) Uani 1 1 d . . .
O1 O 0.17611(9) 0.65150(13) 0.14106(12) 0.0507(4) Uani 1 1 d . . .
C2 C 0.36555(16) 0.3223(3) 0.3234(2) 0.0751(7) Uani 1 1 d . . .
H2 H 0.3707 0.2373 0.3404 0.090 Uiso 1 1 calc R . .
C3 C 0.39812(15) 0.4054(3) 0.4164(2) 0.0702(7) Uani 1 1 d . . .
H3 H 0.4252 0.3775 0.4966 0.084 Uiso 1 1 calc R . .
C4 C 0.39074(16) 0.5306(3) 0.3911(2) 0.0620(7) Uani 1 1 d . . .
H4 H 0.4130 0.5877 0.4545 0.074 Uiso 1 1 calc R . .
C5 C 0.35038(13) 0.5730(2) 0.27204(19) 0.0531(5) Uani 1 1 d . . .
H5 H 0.3462 0.6582 0.2559 0.064 Uiso 1 1 calc R . .
C6 C 0.31603(14) 0.48912(19) 0.1763(2) 0.0456(5) Uani 1 1 d . . .
C7 C 0.27158(14) 0.5342(2) 0.04426(19) 0.0488(5) Uani 1 1 d . . .
H7 H 0.2317 0.4702 0.0097 0.059 Uiso 1 1 calc R . .
C8 C 0.32652(14) 0.5493(2) -0.05127(18) 0.0488(5) Uani 1 1 d . . .
C9 C 0.30066(17) 0.5117(2) -0.1781(2) 0.0607(7) Uani 1 1 d . . .
H9 H 0.2499 0.4759 -0.2036 0.073 Uiso 1 1 calc R . .
C10 C 0.3490(2) 0.5266(3) -0.2670(2) 0.0749(8) Uani 1 1 d . . .
H10 H 0.3304 0.5013 -0.3517 0.090 Uiso 1 1 calc R . .
C11 C 0.42408(19) 0.5784(3) -0.2318(2) 0.0763(8) Uani 1 1 d . . .
H11 H 0.4569 0.5869 -0.2917 0.092 Uiso 1 1 calc R . .
C12 C 0.45083(16) 0.6181(3) -0.1060(2) 0.0729(7) Uani 1 1 d . . .
H12 H 0.5015 0.6545 -0.0812 0.087 Uiso 1 1 calc R . .
C13 C 0.40197(15) 0.6035(2) -0.0178(2) 0.0641(7) Uani 1 1 d . . .
H13 H 0.4203 0.6307 0.0664 0.077 Uiso 1 1 calc R . .
C14 C 0.22648(12) 0.6527(2) 0.05260(17) 0.0474(5) Uani 1 1 d . . .
C15 C 0.22461(13) 0.7645(2) -0.00529(17) 0.0491(5) Uani 1 1 d . . .
H15 H 0.2529 0.7871 -0.0682 0.059 Uiso 1 1 calc R . .
C25 C 0.14723(13) 0.9700(2) 0.03459(19) 0.0492(5) Uani 1 1 d . . .
C16 C 0.17075(12) 0.8429(2) 0.04820(17) 0.0462(5) Uani 1 1 d . . .
C24 C 0.17297(15) 1.0512(2) -0.0533(2) 0.0595(6) Uani 1 1 d . . .
H24 H 0.2046 1.0207 -0.1084 0.071 Uiso 1 1 calc R . .
C17 C 0.14362(12) 0.7694(2) 0.13666(18) 0.0463(5) Uani 1 1 d . . .
C23 C 0.15188(15) 1.1747(3) -0.0585(2) 0.0711(7) Uani 1 1 d . . .
H23 H 0.1695 1.2274 -0.1168 0.085 Uiso 1 1 calc R . .
C18 C 0.09454(12) 0.8120(2) 0.21844(19) 0.0507(5) Uani 1 1 d . . .
H18 H 0.0776 0.7594 0.2774 0.061 Uiso 1 1 calc R . .
C22 C 0.10406(16) 1.2222(2) 0.0232(2) 0.0733(7) Uani 1 1 d . . .
H22 H 0.0902 1.3062 0.0192 0.088 Uiso 1 1 calc R . .
C19 C 0.07286(13) 0.9340(2) 0.20762(19) 0.0505(5) Uani 1 1 d . . .
C21 C 0.07751(14) 1.1456(2) 0.1090(2) 0.0632(6) Uani 1 1 d . . .
H21 H 0.0456 1.1785 0.1626 0.076 Uiso 1 1 calc R . .
C20 C 0.09752(13) 1.0177(2) 0.11780(19) 0.0483(5) Uani 1 1 d . . .
C1 C 0.32462(15) 0.3629(2) 0.2032(2) 0.0634(6) Uani 1 1 d . . .
H1 H 0.3029 0.3049 0.1405 0.076 Uiso 1 1 calc R . .


_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 C19 1.904(2) . ?
O1 C17 1.376(2) . ?
O1 C14 1.392(2) . ?
C2 C3 1.360(4) . ?
C2 C1 1.391(3) . ?
C3 C4 1.369(3) . ?
C4 C5 1.384(3) . ?
C5 C6 1.392(3) . ?
C6 C1 1.384(3) . ?
C6 C7 1.527(3) . ?
C7 C14 1.495(3) . ?
C7 C8 1.519(3) . ?
C8 C13 1.382(3) . ?
C8 C9 1.387(3) . ?
C9 C10 1.379(4) . ?
C10 C11 1.368(4) . ?
C11 C12 1.386(4) . ?
C12 C13 1.380(3) . ?
C14 C15 1.344(3) . ?
C15 C16 1.439(3) . ?
C25 C24 1.409(3) . ?
C25 C16 1.419(3) . ?
C25 C20 1.433(3) . ?
C16 C17 1.374(3) . ?
C24 C23 1.370(3) . ?
C17 C18 1.396(3) . ?
C23 C22 1.398(3) . ?
C18 C19 1.357(3) . ?
C22 C21 1.369(3) . ?
C19 C20 1.432(3) . ?
C21 C20 1.411(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
C17 O1 C14 105.35(15) . . ?
C3 C2 C1 120.8(2) . . ?
C2 C3 C4 119.5(2) . . ?
C3 C4 C5 120.6(2) . . ?
C4 C5 C6 120.6(2) . . ?
C1 C6 C5 118.1(2) . . ?
C1 C6 C7 120.63(19) . . ?
C5 C6 C7 121.28(19) . . ?
C14 C7 C8 109.83(17) . . ?
C14 C7 C6 112.13(17) . . ?
C8 C7 C6 113.05(18) . . ?
C13 C8 C9 117.6(2) . . ?
C13 C8 C7 122.27(18) . . ?
C9 C8 C7 120.1(2) . . ?
C10 C9 C8 121.1(3) . . ?
C11 C10 C9 120.6(2) . . ?
C10 C11 C12 119.4(2) . . ?
C13 C12 C11 119.7(3) . . ?
C12 C13 C8 121.6(2) . . ?
C15 C14 O1 110.87(17) . . ?
C15 C14 C7 134.07(19) . . ?
O1 C14 C7 115.04(17) . . ?
C14 C15 C16 107.32(18) . . ?
C24 C25 C16 122.9(2) . . ?
C24 C25 C20 119.2(2) . . ?
C16 C25 C20 117.92(19) . . ?
C17 C16 C25 119.58(19) . . ?
C17 C16 C15 105.21(19) . . ?
C25 C16 C15 135.05(19) . . ?
C23 C24 C25 120.7(2) . . ?
C16 C17 O1 111.24(18) . . ?
C16 C17 C18 124.2(2) . . ?
O1 C17 C18 124.38(18) . . ?
C24 C23 C22 120.4(2) . . ?
C19 C18 C17 116.63(19) . . ?
C21 C22 C23 120.3(2) . . ?
C18 C19 C20 123.3(2) . . ?
C18 C19 Br1 116.97(16) . . ?
C20 C19 Br1 119.67(17) . . ?
C22 C21 C20 121.3(2) . . ?
C21 C20 C19 123.7(2) . . ?
C21 C20 C25 118.0(2) . . ?
C19 C20 C25 118.3(2) . . ?
C6 C1 C2 120.4(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
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C4 C5 C6 C7 -179.8(2) . . . . ?
C1 C6 C7 C14 145.9(2) . . . . ?
C5 C6 C7 C14 -35.3(3) . . . . ?
C1 C6 C7 C8 -89.2(2) . . . . ?
C5 C6 C7 C8 89.5(2) . . . . ?
C14 C7 C8 C13 83.0(3) . . . . ?
C6 C7 C8 C13 -43.0(3) . . . . ?
C14 C7 C8 C9 -95.0(2) . . . . ?
C6 C7 C8 C9 139.0(2) . . . . ?
C13 C8 C9 C10 0.7(3) . . . . ?
C7 C8 C9 C10 178.8(2) . . . . ?
C8 C9 C10 C11 0.4(4) . . . . ?
C9 C10 C11 C12 -1.2(4) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C11 C12 C13 C8 0.3(4) . . . . ?
C9 C8 C13 C12 -1.1(4) . . . . ?
C7 C8 C13 C12 -179.1(2) . . . . ?
C17 O1 C14 C15 -0.9(2) . . . . ?
C17 O1 C14 C7 177.70(17) . . . . ?
C8 C7 C14 C15 0.4(3) . . . . ?
C6 C7 C14 C15 127.0(3) . . . . ?
C8 C7 C14 O1 -177.79(16) . . . . ?
C6 C7 C14 O1 -51.2(2) . . . . ?
O1 C14 C15 C16 0.6(2) . . . . ?
C7 C14 C15 C16 -177.6(2) . . . . ?
C24 C25 C16 C17 179.6(2) . . . . ?
C20 C25 C16 C17 1.9(3) . . . . ?
C24 C25 C16 C15 4.8(4) . . . . ?
C20 C25 C16 C15 -172.9(2) . . . . ?
C14 C15 C16 C17 -0.1(2) . . . . ?
C14 C15 C16 C25 175.2(2) . . . . ?
C16 C25 C24 C23 -176.8(2) . . . . ?
C20 C25 C24 C23 0.9(3) . . . . ?
C25 C16 C17 O1 -176.68(17) . . . . ?
C15 C16 C17 O1 -0.5(2) . . . . ?
C25 C16 C17 C18 -1.4(3) . . . . ?
C15 C16 C17 C18 174.82(18) . . . . ?
C14 O1 C17 C16 0.9(2) . . . . ?
C14 O1 C17 C18 -174.45(18) . . . . ?
C25 C24 C23 C22 -0.3(4) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
O1 C17 C18 C19 174.95(19) . . . . ?
C24 C23 C22 C21 -0.2(4) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C17 C18 C19 Br1 -177.92(14) . . . . ?
C23 C22 C21 C20 0.1(4) . . . . ?
C22 C21 C20 C19 178.6(2) . . . . ?
C22 C21 C20 C25 0.5(3) . . . . ?
C18 C19 C20 C21 -177.8(2) . . . . ?
Br1 C19 C20 C21 0.4(3) . . . . ?
C18 C19 C20 C25 0.4(3) . . . . ?
Br1 C19 C20 C25 178.51(15) . . . . ?
C24 C25 C20 C21 -0.9(3) . . . . ?
C16 C25 C20 C21 176.8(2) . . . . ?
C24 C25 C20 C19 -179.2(2) . . . . ?
C16 C25 C20 C19 -1.5(3) . . . . ?
C5 C6 C1 C2 0.9(3) . . . . ?
C7 C6 C1 C2 179.6(2) . . . . ?
C3 C2 C1 C6 -0.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.048
