# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_xb9728_0m
_database_code_depnum_ccdc_archive 'CCDC 2010458'
loop_
_audit_author_name
_audit_author_address
'BoJun Tan'
;NWU
China
;
_audit_update_record             
;
2020-06-17 deposited with the CCDC.	2020-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 O'
_chemical_formula_weight         322.38

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   29.083(12)
_cell_length_b                   9.001(4)
_cell_length_c                   13.882(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.729(8)
_cell_angle_gamma                90
_cell_volume                     3530(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1640
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      22.40

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.285
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8583
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.442
_diffrn_reflns_theta_max         25.096
_diffrn_reflns_theta_full        25.096
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3130
_reflns_number_gt                2136
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0676P)²+1.0715P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3130
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1405
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
O1 O 0.10536(7) 0.39178(18) 0.76160(13) 0.0698(5) Uani 1 1 d . . . . .
C1 C 0.10160(7) 0.2581(2) 0.74665(16) 0.0470(5) Uani 1 1 d . . . . .
C2 C 0.08588(10) 0.1587(3) 0.81531(19) 0.0682(7) Uani 1 1 d . . . . .
H2 H 0.0730 0.1990 0.8647 0.082 Uiso 1 1 calc R U . . .
C3 C 0.08956(10) 0.0108(3) 0.80920(18) 0.0685(7) Uani 1 1 d . . . . .
H3 H 0.0792 -0.0477 0.8551 0.082 Uiso 1 1 calc R U . . .
C4 C 0.10896(8) -0.0626(2) 0.73445(16) 0.0482(6) Uani 1 1 d . . . . .
C5 C 0.11781(9) -0.2173(3) 0.73772(19) 0.0613(7) Uani 1 1 d . . . . .
H5 H 0.1106 -0.2736 0.7884 0.074 Uiso 1 1 calc R U . . .
C6 C 0.13678(8) -0.2863(3) 0.6676(2) 0.0615(7) Uani 1 1 d . . . . .
H6 H 0.1425 -0.3880 0.6710 0.074 Uiso 1 1 calc R U . . .
C7 C 0.14721(8) -0.2035(2) 0.5927(2) 0.0563(6) Uani 1 1 d . . . . .
H7 H 0.1600 -0.2495 0.5450 0.068 Uiso 1 1 calc R U . . .
C8 C 0.13881(7) -0.0507(2) 0.58758(17) 0.0454(5) Uani 1 1 d . . . . .
H8 H 0.1458 0.0037 0.5359 0.055 Uiso 1 1 calc R U . . .
C9 C 0.12031(6) 0.0215(2) 0.65825(14) 0.0371(5) Uani 1 1 d . . . . .
C10 C 0.11189(7) 0.1898(2) 0.65193(14) 0.0361(5) Uani 1 1 d . . . . .
C11 C 0.06894(7) 0.2300(2) 0.56720(14) 0.0369(5) Uani 1 1 d . . . . .
C12 C 0.02244(7) 0.1843(2) 0.55284(17) 0.0499(6) Uani 1 1 d . . . . .
H12 H 0.0137 0.1175 0.5964 0.060 Uiso 1 1 calc R U . . .
C13 C -0.01105(8) 0.2399(3) 0.47221(19) 0.0615(7) Uani 1 1 d . . . . .
H13 H -0.0424 0.2098 0.4617 0.074 Uiso 1 1 calc R U . . .
C14 C 0.00195(9) 0.3401(3) 0.40725(19) 0.0622(7) Uani 1 1 d . . . . .
H14 H -0.0210 0.3777 0.3544 0.075 Uiso 1 1 calc R U . . .
C15 C 0.04871(8) 0.3846(2) 0.42019(16) 0.0508(6) Uani 1 1 d . . . . .
H15 H 0.0573 0.4506 0.3760 0.061 Uiso 1 1 calc R U . . .
C16 C 0.08245(7) 0.3289(2) 0.50038(15) 0.0379(5) Uani 1 1 d . . . . .
C17 C 0.13391(7) 0.3520(2) 0.53145(15) 0.0375(5) Uani 1 1 d . . . . .
C18 C 0.15164(7) 0.2735(2) 0.61966(14) 0.0365(5) Uani 1 1 d . . . . .
C19 C 0.19967(7) 0.2746(2) 0.66556(16) 0.0453(5) Uani 1 1 d . . . . .
C20 C 0.22937(8) 0.3542(2) 0.61801(19) 0.0533(6) Uani 1 1 d . . . . .
H20 H 0.2617 0.3552 0.6466 0.064 Uiso 1 1 calc R U . . .
C21 C 0.21263(8) 0.4320(2) 0.52985(19) 0.0507(6) Uani 1 1 d . . . . .
C22 C 0.16453(8) 0.4313(2) 0.48634(17) 0.0469(6) Uani 1 1 d . . . . .
H22 H 0.1527 0.4831 0.4277 0.056 Uiso 1 1 calc R U . . .
C23 C 0.24670(10) 0.5142(3) 0.4813(2) 0.0797(9) Uani 1 1 d . . . . .
H23A H 0.2375 0.4999 0.4108 0.120 Uiso 1 1 calc R U . . .
H23B H 0.2781 0.4764 0.5064 0.120 Uiso 1 1 calc R U . . .
H23C H 0.2461 0.6182 0.4961 0.120 Uiso 1 1 calc R U . . .
C24 C 0.21937(9) 0.1918(3) 0.7609(2) 0.0700(8) Uani 1 1 d . . . . .
H24A H 0.2006 0.2135 0.8076 0.105 Uiso 1 1 calc R U . . .
H24B H 0.2515 0.2222 0.7879 0.105 Uiso 1 1 calc R U . . .
H24C H 0.2185 0.0869 0.7479 0.105 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
O1 C1 1.222(3) . ?
C1 C2 1.458(3) . ?
C1 C10 1.544(3) . ?
C2 C3 1.340(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.452(3) . ?
C3 H3 0.9300 . ?
C4 C9 1.403(3) . ?
C4 C5 1.414(3) . ?
C5 C6 1.375(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.370(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.396(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.534(3) . ?
C10 C18 1.533(3) . ?
C10 C11 1.542(3) . ?
C11 C12 1.382(3) . ?
C11 C16 1.407(3) . ?
C12 C13 1.391(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.388(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.471(3) . ?
C17 C22 1.400(3) . ?
C17 C18 1.402(3) . ?
C18 C19 1.391(3) . ?
C19 C20 1.402(3) . ?
C19 C24 1.509(3) . ?
C20 C21 1.393(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.386(3) . ?
C21 C23 1.517(3) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
O1 C1 C2 121.5(2) . . ?
O1 C1 C10 120.60(19) . . ?
C2 C1 C10 117.85(19) . . ?
C3 C2 C1 121.8(2) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 123.2(2) . . ?
C2 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
C9 C4 C5 118.8(2) . . ?
C9 C4 C3 119.6(2) . . ?
C5 C4 C3 121.6(2) . . ?
C6 C5 C4 121.5(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C7 C6 C5 119.3(2) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C8 120.5(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 121.2(2) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C4 118.74(19) . . ?
C8 C9 C10 120.37(17) . . ?
C4 C9 C10 120.88(18) . . ?
C18 C10 C9 112.36(15) . . ?
C18 C10 C11 101.10(15) . . ?
C9 C10 C11 111.38(15) . . ?
C18 C10 C1 111.46(15) . . ?
C9 C10 C1 113.88(16) . . ?
C11 C10 C1 105.71(16) . . ?
C12 C11 C16 120.65(19) . . ?
C12 C11 C10 128.91(18) . . ?
C16 C11 C10 110.42(16) . . ?
C11 C12 C13 118.9(2) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 120.8(2) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 118.9(2) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C15 C16 C11 120.10(19) . . ?
C15 C16 C17 131.23(19) . . ?
C11 C16 C17 108.67(17) . . ?
C22 C17 C18 120.45(19) . . ?
C22 C17 C16 130.70(19) . . ?
C18 C17 C16 108.81(16) . . ?
C19 C18 C17 121.17(18) . . ?
C19 C18 C10 127.94(18) . . ?
C17 C18 C10 110.88(17) . . ?
C18 C19 C20 116.9(2) . . ?
C18 C19 C24 122.0(2) . . ?
C20 C19 C24 121.2(2) . . ?
C21 C20 C19 123.0(2) . . ?
C21 C20 H20 118.5 . . ?
C19 C20 H20 118.5 . . ?
C22 C21 C20 119.1(2) . . ?
C22 C21 C23 120.5(2) . . ?
C20 C21 C23 120.4(2) . . ?
C21 C22 C17 119.4(2) . . ?
C21 C22 H22 120.3 . . ?
C17 C22 H22 120.3 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
O1 C1 C2 C3 -168.0(3) . . . . ?
C10 C1 C2 C3 13.9(4) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 C9 -6.6(4) . . . . ?
C2 C3 C4 C5 171.9(3) . . . . ?
C9 C4 C5 C6 -0.6(3) . . . . ?
C3 C4 C5 C6 -179.1(2) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C6 C7 C8 C9 0.7(3) . . . . ?
C7 C8 C9 C4 -1.5(3) . . . . ?
C7 C8 C9 C10 179.27(19) . . . . ?
C5 C4 C9 C8 1.4(3) . . . . ?
C3 C4 C9 C8 180.0(2) . . . . ?
C5 C4 C9 C10 -179.37(19) . . . . ?
C3 C4 C9 C10 -0.8(3) . . . . ?
C8 C9 C10 C18 -39.6(2) . . . . ?
C4 C9 C10 C18 141.26(19) . . . . ?
C8 C9 C10 C11 73.1(2) . . . . ?
C4 C9 C10 C11 -106.1(2) . . . . ?
C8 C9 C10 C1 -167.50(17) . . . . ?
C4 C9 C10 C1 13.3(3) . . . . ?
O1 C1 C10 C18 34.1(3) . . . . ?
C2 C1 C10 C18 -147.9(2) . . . . ?
O1 C1 C10 C9 162.5(2) . . . . ?
C2 C1 C10 C9 -19.5(3) . . . . ?
O1 C1 C10 C11 -74.9(2) . . . . ?
C2 C1 C10 C11 103.1(2) . . . . ?
C18 C10 C11 C12 178.17(19) . . . . ?
C9 C10 C11 C12 58.6(3) . . . . ?
C1 C10 C11 C12 -65.6(2) . . . . ?
C18 C10 C11 C16 -2.99(19) . . . . ?
C9 C10 C11 C16 -122.54(17) . . . . ?
C1 C10 C11 C16 113.28(18) . . . . ?
C16 C11 C12 C13 -1.2(3) . . . . ?
C10 C11 C12 C13 177.5(2) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C12 C13 C14 C15 1.3(4) . . . . ?
C13 C14 C15 C16 -0.9(4) . . . . ?
C14 C15 C16 C11 -0.5(3) . . . . ?
C14 C15 C16 C17 178.2(2) . . . . ?
C12 C11 C16 C15 1.6(3) . . . . ?
C10 C11 C16 C15 -177.36(18) . . . . ?
C12 C11 C16 C17 -177.38(17) . . . . ?
C10 C11 C16 C17 3.7(2) . . . . ?
C15 C16 C17 C22 -3.8(4) . . . . ?
C11 C16 C17 C22 175.06(19) . . . . ?
C15 C16 C17 C18 178.4(2) . . . . ?
C11 C16 C17 C18 -2.8(2) . . . . ?
C22 C17 C18 C19 1.3(3) . . . . ?
C16 C17 C18 C19 179.45(17) . . . . ?
C22 C17 C18 C10 -177.29(17) . . . . ?
C16 C17 C18 C10 0.8(2) . . . . ?
C9 C10 C18 C19 -58.4(3) . . . . ?
C11 C10 C18 C19 -177.26(19) . . . . ?
C1 C10 C18 C19 70.8(2) . . . . ?
C9 C10 C18 C17 120.08(18) . . . . ?
C11 C10 C18 C17 1.23(19) . . . . ?
C1 C10 C18 C17 -110.71(19) . . . . ?
C17 C18 C19 C20 -1.7(3) . . . . ?
C10 C18 C19 C20 176.62(18) . . . . ?
C17 C18 C19 C24 179.5(2) . . . . ?
C10 C18 C19 C24 -2.2(3) . . . . ?
C18 C19 C20 C21 1.1(3) . . . . ?
C24 C19 C20 C21 179.9(2) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C19 C20 C21 C23 -179.1(2) . . . . ?
C20 C21 C22 C17 -0.4(3) . . . . ?
C23 C21 C22 C17 178.65(19) . . . . ?
C18 C17 C22 C21 -0.2(3) . . . . ?
C16 C17 C22 C21 -177.87(19) . . . . ?

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_xb9862_0m
_database_code_depnum_ccdc_archive 'CCDC 2010459'
loop_
_audit_author_name
_audit_author_address
'BoJun Tan'
;NWU
China
;
_audit_update_record             
;
2020-06-17 deposited with the CCDC.	2020-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H15 Br O2'
_chemical_formula_weight         403.26

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)/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                   8.218(5)
_cell_length_b                   12.135(7)
_cell_length_c                   18.051(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.865(10)
_cell_angle_gamma                90.00
_cell_volume                     1778.8(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    805
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      18.60

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    2.325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4933
_exptl_absorpt_correction_T_max  0.7489
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8569
_diffrn_reflns_av_R_equivalents  0.1151
_diffrn_reflns_av_sigmaI/netI    0.1546
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         25.10
_reflns_number_total             3173
_reflns_number_gt                1290
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0914P)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         3173
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1824
_refine_ls_R_factor_gt           0.0661
_refine_ls_wR_factor_ref         0.2130
_refine_ls_wR_factor_gt          0.1505
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_restrained_S_all      0.955
_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 0.17752(13) -0.12806(9) 1.06651(6) 0.0891(5) Uani 1 1 d . . .
O1 O -0.2169(8) 0.1559(5) 0.5728(3) 0.0694(16) Uani 1 1 d . . .
O2 O 0.5123(7) 0.2527(4) 0.7493(3) 0.0741(18) Uani 1 1 d . . .
C1 C 0.2851(10) 0.0466(7) 0.9835(4) 0.065(2) Uani 1 1 d . . .
H1 H 0.2829 0.0869 1.0272 0.077 Uiso 1 1 calc R . .
C2 C 0.2441(10) -0.0638(7) 0.9807(5) 0.060(2) Uani 1 1 d . . .
C3 C 0.2442(11) -0.1237(6) 0.9169(5) 0.065(2) Uani 1 1 d . . .
H3 H 0.2143 -0.1977 0.9151 0.078 Uiso 1 1 calc R . .
C4 C 0.2895(10) -0.0724(6) 0.8551(5) 0.066(2) Uani 1 1 d . . .
H4 H 0.2913 -0.1133 0.8116 0.079 Uiso 1 1 calc R . .
C5 C 0.3323(9) 0.0377(6) 0.8557(4) 0.0465(19) Uani 1 1 d . . .
C6 C 0.3294(9) 0.0967(6) 0.9208(5) 0.055(2) Uani 1 1 d . . .
C7 C 0.3718(12) 0.2128(7) 0.9231(5) 0.075(3) Uani 1 1 d . . .
H7 H 0.3597 0.2528 0.9659 0.091 Uiso 1 1 calc R . .
C8 C 0.4278(11) 0.2654(7) 0.8662(5) 0.066(2) Uani 1 1 d . . .
H8 H 0.4579 0.3391 0.8725 0.080 Uiso 1 1 calc R . .
C9 C 0.4429(10) 0.2126(6) 0.7965(5) 0.054(2) Uani 1 1 d . . .
C10 C 0.3579(10) 0.0974(6) 0.7831(4) 0.053(2) Uani 1 1 d . . .
C11 C 0.4461(10) 0.0288(6) 0.7306(4) 0.049(2) Uani 1 1 d . . .
C12 C 0.5985(10) -0.0172(6) 0.7419(5) 0.058(2) Uani 1 1 d . . .
H12 H 0.6652 -0.0121 0.7883 0.070 Uiso 1 1 calc R . .
C13 C 0.6525(13) -0.0715(7) 0.6834(6) 0.073(3) Uani 1 1 d . . .
H13 H 0.7556 -0.1048 0.6912 0.087 Uiso 1 1 calc R . .
C14 C 0.5593(12) -0.0779(7) 0.6141(6) 0.067(3) Uani 1 1 d . . .
H14 H 0.6016 -0.1118 0.5750 0.080 Uiso 1 1 calc R . .
C15 C 0.4064(12) -0.0352(6) 0.6023(4) 0.063(2) Uani 1 1 d . . .
H15 H 0.3404 -0.0430 0.5559 0.075 Uiso 1 1 calc R . .
C16 C 0.3475(10) 0.0214(5) 0.6607(5) 0.051(2) Uani 1 1 d . . .
C17 C 0.1858(10) 0.0775(6) 0.6633(4) 0.049(2) Uani 1 1 d . . .
C18 C 0.0478(11) 0.0908(6) 0.6102(4) 0.058(2) Uani 1 1 d . . .
H18 H 0.0453 0.0630 0.5620 0.069 Uiso 1 1 calc R . .
C19 C -0.0886(10) 0.1465(6) 0.6295(5) 0.053(2) Uani 1 1 d . . .
C20 C -0.0876(10) 0.1869(6) 0.7009(5) 0.057(2) Uani 1 1 d . . .
H20 H -0.1797 0.2221 0.7139 0.068 Uiso 1 1 calc R . .
C21 C 0.0515(11) 0.1743(6) 0.7521(5) 0.056(2) Uani 1 1 d . . .
H21 H 0.0532 0.2025 0.8001 0.067 Uiso 1 1 calc R . .
C22 C 0.1896(9) 0.1212(5) 0.7353(4) 0.0452(19) Uani 1 1 d . . .
C23 C -0.3611(11) 0.2111(8) 0.5901(5) 0.079(3) Uani 1 1 d . . .
H23A H -0.4000 0.1742 0.6310 0.118 Uiso 1 1 calc R . .
H23B H -0.4455 0.2099 0.5469 0.118 Uiso 1 1 calc R . .
H23C H -0.3342 0.2861 0.6038 0.118 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 C2 1.890(7) . ?
O1 C19 1.357(10) . ?
O1 C23 1.437(9) . ?
O2 C9 1.200(8) . ?
C1 C2 1.380(11) . ?
C1 C6 1.383(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.361(11) . ?
C3 C4 1.377(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(10) . ?
C5 C10 1.540(10) . ?
C6 C7 1.450(11) . ?
C7 C8 1.349(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.434(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.565(10) . ?
C10 C11 1.525(9) . ?
C10 C22 1.540(11) . ?
C11 C12 1.358(10) . ?
C11 C16 1.393(11) . ?
C12 C13 1.375(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.364(12) . ?
C13 H13 0.9300 . ?
C14 C15 1.345(11) . ?
C14 H14 0.9300 . ?
C15 C16 1.406(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.500(10) . ?
C17 C18 1.378(11) . ?
C17 C22 1.400(9) . ?
C18 C19 1.399(10) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(10) . ?
C20 C21 1.363(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.379(10) . ?
C21 H21 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O1 C23 116.5(6) . . ?
C2 C1 C6 119.3(7) . . ?
C2 C1 H1 120.3 . . ?
C6 C1 H1 120.3 . . ?
C3 C2 C1 121.2(7) . . ?
C3 C2 Br1 120.7(7) . . ?
C1 C2 Br1 118.0(7) . . ?
C2 C3 C4 118.6(8) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C3 C4 C5 122.1(8) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 118.1(7) . . ?
C6 C5 C10 120.3(6) . . ?
C4 C5 C10 121.1(7) . . ?
C5 C6 C1 120.7(7) . . ?
C5 C6 C7 119.6(7) . . ?
C1 C6 C7 119.7(7) . . ?
C8 C7 C6 123.1(8) . . ?
C8 C7 H7 118.4 . . ?
C6 C7 H7 118.4 . . ?
C7 C8 C9 122.8(8) . . ?
C7 C8 H8 118.6 . . ?
C9 C8 H8 118.6 . . ?
O2 C9 C8 123.9(8) . . ?
O2 C9 C10 120.1(7) . . ?
C8 C9 C10 116.0(7) . . ?
C11 C10 C22 103.2(6) . . ?
C11 C10 C5 114.3(6) . . ?
C22 C10 C5 109.6(6) . . ?
C11 C10 C9 109.9(6) . . ?
C22 C10 C9 105.1(6) . . ?
C5 C10 C9 113.8(6) . . ?
C12 C11 C16 120.2(7) . . ?
C12 C11 C10 130.4(8) . . ?
C16 C11 C10 109.3(7) . . ?
C11 C12 C13 118.8(8) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C14 C13 C12 121.9(9) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C15 C14 C13 120.2(8) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 119.4(8) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C11 C16 C15 119.4(8) . . ?
C11 C16 C17 109.7(6) . . ?
C15 C16 C17 130.9(8) . . ?
C18 C17 C22 120.0(7) . . ?
C18 C17 C16 132.0(7) . . ?
C22 C17 C16 107.9(7) . . ?
C17 C18 C19 119.2(7) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
O1 C19 C20 124.6(7) . . ?
O1 C19 C18 114.3(7) . . ?
C20 C19 C18 121.1(8) . . ?
C21 C20 C19 118.5(8) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C20 C21 C22 122.4(8) . . ?
C20 C21 H21 118.8 . . ?
C22 C21 H21 118.8 . . ?
C21 C22 C17 118.7(7) . . ?
C21 C22 C10 131.6(7) . . ?
C17 C22 C10 109.7(6) . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
C6 C1 C2 C3 -1.0(13) . . . . ?
C6 C1 C2 Br1 -178.0(6) . . . . ?
C1 C2 C3 C4 1.3(13) . . . . ?
Br1 C2 C3 C4 178.2(6) . . . . ?
C2 C3 C4 C5 -0.9(13) . . . . ?
C3 C4 C5 C6 0.2(12) . . . . ?
C3 C4 C5 C10 -171.0(8) . . . . ?
C4 C5 C6 C1 0.1(11) . . . . ?
C10 C5 C6 C1 171.4(7) . . . . ?
C4 C5 C6 C7 -179.3(8) . . . . ?
C10 C5 C6 C7 -8.0(11) . . . . ?
C2 C1 C6 C5 0.3(12) . . . . ?
C2 C1 C6 C7 179.7(8) . . . . ?
C5 C6 C7 C8 -5.6(13) . . . . ?
C1 C6 C7 C8 175.0(9) . . . . ?
C6 C7 C8 C9 3.2(15) . . . . ?
C7 C8 C9 O2 -169.7(9) . . . . ?
C7 C8 C9 C10 12.0(12) . . . . ?
C6 C5 C10 C11 149.3(7) . . . . ?
C4 C5 C10 C11 -39.7(10) . . . . ?
C6 C5 C10 C22 -95.5(8) . . . . ?
C4 C5 C10 C22 75.5(8) . . . . ?
C6 C5 C10 C9 21.9(10) . . . . ?
C4 C5 C10 C9 -167.1(7) . . . . ?
O2 C9 C10 C11 28.7(10) . . . . ?
C8 C9 C10 C11 -152.9(7) . . . . ?
O2 C9 C10 C22 -81.7(8) . . . . ?
C8 C9 C10 C22 96.7(8) . . . . ?
O2 C9 C10 C5 158.3(7) . . . . ?
C8 C9 C10 C5 -23.3(10) . . . . ?
C22 C10 C11 C12 -179.3(7) . . . . ?
C5 C10 C11 C12 -60.4(10) . . . . ?
C9 C10 C11 C12 69.0(10) . . . . ?
C22 C10 C11 C16 4.0(7) . . . . ?
C5 C10 C11 C16 123.0(7) . . . . ?
C9 C10 C11 C16 -107.6(7) . . . . ?
C16 C11 C12 C13 -0.5(11) . . . . ?
C10 C11 C12 C13 -176.8(7) . . . . ?
C11 C12 C13 C14 1.7(12) . . . . ?
C12 C13 C14 C15 -3.4(13) . . . . ?
C13 C14 C15 C16 3.6(12) . . . . ?
C12 C11 C16 C15 0.8(11) . . . . ?
C10 C11 C16 C15 177.9(6) . . . . ?
C12 C11 C16 C17 179.4(6) . . . . ?
C10 C11 C16 C17 -3.5(8) . . . . ?
C14 C15 C16 C11 -2.4(11) . . . . ?
C14 C15 C16 C17 179.3(7) . . . . ?
C11 C16 C17 C18 -178.6(8) . . . . ?
C15 C16 C17 C18 -0.2(13) . . . . ?
C11 C16 C17 C22 1.4(8) . . . . ?
C15 C16 C17 C22 179.9(7) . . . . ?
C22 C17 C18 C19 -1.1(11) . . . . ?
C16 C17 C18 C19 178.9(7) . . . . ?
C23 O1 C19 C20 -0.7(11) . . . . ?
C23 O1 C19 C18 179.1(6) . . . . ?
C17 C18 C19 O1 179.4(6) . . . . ?
C17 C18 C19 C20 -0.8(11) . . . . ?
O1 C19 C20 C21 -178.3(7) . . . . ?
C18 C19 C20 C21 1.9(11) . . . . ?
C19 C20 C21 C22 -1.0(11) . . . . ?
C20 C21 C22 C17 -0.9(11) . . . . ?
C20 C21 C22 C10 180.0(7) . . . . ?
C18 C17 C22 C21 1.9(10) . . . . ?
C16 C17 C22 C21 -178.1(6) . . . . ?
C18 C17 C22 C10 -178.7(6) . . . . ?
C16 C17 C22 C10 1.2(7) . . . . ?
C11 C10 C22 C21 176.0(7) . . . . ?
C5 C10 C22 C21 53.9(9) . . . . ?
C9 C10 C22 C21 -68.8(9) . . . . ?
C11 C10 C22 C17 -3.2(7) . . . . ?
C5 C10 C22 C17 -125.3(6) . . . . ?
C9 C10 C22 C17 112.0(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.081
