# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_mo_d8v18746_0m
_database_code_depnum_ccdc_archive 'CCDC 1868700'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2018-09-20 deposited with the CCDC.	2019-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 O'
_chemical_formula_weight         288.37

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   10.069(3)
_cell_length_b                   5.4426(14)
_cell_length_c                   14.511(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.633(8)
_cell_angle_gamma                90
_cell_volume                     788.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1543
_cell_measurement_theta_min      5.268
_cell_measurement_theta_max      52.877

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_F_000             308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5460
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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            3568
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.324
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_point_group_measured_fraction_full 0.832
_reflns_number_total             2370
_reflns_number_gt                1826
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.535
_reflns_Friedel_fraction_max     0.668
_reflns_Friedel_fraction_full    0.656

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0685P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.025(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 561 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -2.4(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2370
_refine_ls_number_parameters     209
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1389
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.3620(2) 0.7602(5) 0.30247(16) 0.0518(7) Uani 1 1 d . . . . .
C1 C 0.2680(4) 0.7444(9) 0.2255(2) 0.0537(10) Uani 1 1 d . . . . .
H1 H 0.1925 0.8497 0.2130 0.064 Uiso 1 1 calc R U . . .
C2 C 0.2965(3) 0.5614(8) 0.1702(2) 0.0459(9) Uani 1 1 d . . . . .
C3 C 0.4169(3) 0.4499(7) 0.2148(2) 0.0437(9) Uani 1 1 d . . . . .
C4 C 0.4540(3) 0.5781(7) 0.2944(2) 0.0432(9) Uani 1 1 d . . . . .
C5 C 0.5653(3) 0.5709(7) 0.3704(2) 0.0425(9) Uani 1 1 d . . . . .
C6 C 0.6628(4) 0.3909(9) 0.3775(3) 0.0608(12) Uani 1 1 d . . . . .
H6 H 0.6594 0.2677 0.3308 0.073 Uiso 1 1 calc R U . . .
C7 C 0.7653(4) 0.3863(8) 0.4510(3) 0.0595(12) Uani 1 1 d . . . . .
H7 H 0.8297 0.2581 0.4540 0.071 Uiso 1 1 calc R U . . .
C8 C 0.7770(3) 0.5619(7) 0.5203(2) 0.0397(8) Uani 1 1 d . . . . .
C9 C 0.6803(4) 0.7443(9) 0.5111(3) 0.0554(11) Uani 1 1 d . . . . .
H9 H 0.6852 0.8714 0.5563 0.066 Uiso 1 1 calc R U . . .
C10 C 0.5776(4) 0.7476(9) 0.4389(3) 0.0564(10) Uani 1 1 d . . . . .
H10 H 0.5131 0.8756 0.4361 0.068 Uiso 1 1 calc R U . . .
C11 C 0.8868(3) 0.5553(7) 0.5993(2) 0.0398(8) Uani 1 1 d . . . . .
C12 C 0.9802(4) 0.3689(8) 0.6095(3) 0.0541(11) Uani 1 1 d . . . . .
H12 H 0.9747 0.2409 0.5646 0.065 Uiso 1 1 calc R U . . .
C13 C 1.0823(4) 0.3641(9) 0.6838(3) 0.0607(12) Uani 1 1 d . . . . .
H13 H 1.1458 0.2340 0.6886 0.073 Uiso 1 1 calc R U . . .
C14 C 1.0928(4) 0.5439(9) 0.7501(3) 0.0552(11) Uani 1 1 d . . . . .
H14 H 1.1618 0.5381 0.8015 0.066 Uiso 1 1 calc R U . . .
C15 C 1.0020(4) 0.7326(9) 0.7410(3) 0.0613(11) Uani 1 1 d . . . . .
H15 H 1.0086 0.8606 0.7859 0.074 Uiso 1 1 calc R U . . .
C16 C 0.9010(4) 0.7370(8) 0.6669(3) 0.0561(10) Uani 1 1 d . . . . .
H16 H 0.8389 0.8693 0.6620 0.067 Uiso 1 1 calc R U . . .
C17 C 0.2182(4) 0.4850(8) 0.0797(2) 0.0542(11) Uani 1 1 d . . . . .
H17A H 0.1752 0.3245 0.0882 0.065 Uiso 1 1 calc R U . . .
H17B H 0.2807 0.4627 0.0332 0.065 Uiso 1 1 calc R U . . .
C18 C 0.1114(4) 0.6676(9) 0.0424(3) 0.0649(13) Uani 1 1 d . . . . .
H18A H 0.0691 0.6141 -0.0191 0.097 Uiso 1 1 calc R U . . .
H18B H 0.1523 0.8296 0.0372 0.097 Uiso 1 1 calc R U . . .
H18C H 0.0436 0.6776 0.0848 0.097 Uiso 1 1 calc R U . . .
C19 C 0.4863(4) 0.2418(8) 0.1737(3) 0.0540(10) Uani 1 1 d . . . . .
H19A H 0.5277 0.1345 0.2246 0.065 Uiso 1 1 calc R U . . .
H19B H 0.4187 0.1430 0.1339 0.065 Uiso 1 1 calc R U . . .
C20 C 0.5920(5) 0.3212(11) 0.1170(3) 0.0706(14) Uani 1 1 d . . . . .
H20 H 0.6282 0.1968 0.0818 0.085 Uiso 1 1 calc R U . . .
C21 C 0.6392(6) 0.5362(15) 0.1106(4) 0.094(2) Uani 1 1 d . . . . .
H21A H 0.710(5) 0.561(12) 0.074(4) 0.13(2) Uiso 1 1 d . . . . .
H21B H 0.606(5) 0.701(12) 0.154(4) 0.123(19) Uiso 1 1 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
O1 C1 1.368(4) . ?
O1 C4 1.373(4) . ?
C1 C2 1.334(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.431(5) . ?
C2 C17 1.499(5) . ?
C3 C4 1.359(5) . ?
C3 C19 1.496(5) . ?
C4 C5 1.465(5) . ?
C5 C10 1.377(5) . ?
C5 C6 1.381(5) . ?
C6 C7 1.383(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(5) . ?
C8 C11 1.483(5) . ?
C9 C10 1.370(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.379(5) . ?
C11 C16 1.387(5) . ?
C12 C13 1.387(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.366(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.370(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.510(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.492(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.271(8) . ?
C20 H20 0.9500 . ?
C21 H21A 0.95(5) . ?
C21 H21B 1.17(6) . ?

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
C1 O1 C4 106.6(3) . . ?
C2 C1 O1 110.9(3) . . ?
C2 C1 H1 124.5 . . ?
O1 C1 H1 124.5 . . ?
C1 C2 C3 106.4(3) . . ?
C1 C2 C17 127.2(3) . . ?
C3 C2 C17 126.4(3) . . ?
C4 C3 C2 106.7(3) . . ?
C4 C3 C19 129.6(3) . . ?
C2 C3 C19 123.6(3) . . ?
C3 C4 O1 109.3(3) . . ?
C3 C4 C5 136.3(3) . . ?
O1 C4 C5 114.4(3) . . ?
C10 C5 C6 116.5(3) . . ?
C10 C5 C4 120.8(3) . . ?
C6 C5 C4 122.7(3) . . ?
C7 C6 C5 121.4(4) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C8 C7 C6 122.2(4) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C9 115.8(4) . . ?
C7 C8 C11 121.9(3) . . ?
C9 C8 C11 122.3(3) . . ?
C10 C9 C8 122.2(4) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C9 C10 C5 122.0(4) . . ?
C9 C10 H10 119.0 . . ?
C5 C10 H10 119.0 . . ?
C12 C11 C16 116.4(3) . . ?
C12 C11 C8 121.9(3) . . ?
C16 C11 C8 121.7(3) . . ?
C11 C12 C13 121.5(4) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 120.9(4) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 118.7(4) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C14 C15 C16 120.1(4) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 122.4(4) . . ?
C15 C16 H16 118.8 . . ?
C11 C16 H16 118.8 . . ?
C2 C17 C18 113.5(3) . . ?
C2 C17 H17A 108.9 . . ?
C18 C17 H17A 108.9 . . ?
C2 C17 H17B 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C3 113.9(4) . . ?
C20 C19 H19A 108.8 . . ?
C3 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
C3 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C21 C20 C19 127.4(5) . . ?
C21 C20 H20 116.3 . . ?
C19 C20 H20 116.3 . . ?
C20 C21 H21A 119(4) . . ?
C20 C21 H21B 122(3) . . ?
H21A C21 H21B 119(5) . . ?

_refine_diff_density_max         0.134
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.034

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_d8v18842_0m
_database_code_depnum_ccdc_archive 'CCDC 1874229'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2018-10-19 deposited with the CCDC.	2019-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 I2 O'
_chemical_formula_weight         464.06

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'
I I -0.4742 1.8119 '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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   5.7795(15)
_cell_length_b                   7.8483(18)
_cell_length_c                   34.692(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.786(10)
_cell_angle_gamma                90
_cell_volume                     1572.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3182
_cell_measurement_theta_min      4.699
_cell_measurement_theta_max      54.331

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.960
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    3.986
_shelx_estimated_absorpt_T_min   0.551
_shelx_estimated_absorpt_T_max   0.646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4012
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_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            6685
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.661
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2884
_reflns_number_gt                2026
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0808P)²+9.2098P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0033(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2884
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0650
_refine_ls_wR_factor_ref         0.1865
_refine_ls_wR_factor_gt          0.1667
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.003
_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
I1 I 0.58746(18) 0.90508(9) 0.43761(2) 0.0913(5) Uani 1 1 d . . . . .
I2 I 0.95305(14) 0.25412(10) 0.47994(3) 0.0856(4) Uani 1 1 d . . . . .
O1 O 0.2859(12) 0.7641(8) 0.37545(19) 0.0579(16) Uani 1 1 d . . . . .
C1 C -0.1339(19) 0.7502(14) 0.3267(3) 0.069(3) Uani 1 1 d . . . . .
H1 H -0.1438 0.8219 0.3479 0.083 Uiso 1 1 calc R U . . .
C2 C -0.300(2) 0.7628(17) 0.2975(4) 0.085(4) Uani 1 1 d . . . . .
H2 H -0.4197 0.8410 0.2992 0.102 Uiso 1 1 calc R U . . .
C3 C -0.286(2) 0.6588(18) 0.2658(4) 0.083(4) Uani 1 1 d . . . . .
H3 H -0.3989 0.6655 0.2461 0.100 Uiso 1 1 calc R U . . .
C4 C -0.109(2) 0.5467(18) 0.2629(3) 0.080(4) Uani 1 1 d . . . . .
H4 H -0.0984 0.4795 0.2409 0.096 Uiso 1 1 calc R U . . .
C5 C 0.0578(16) 0.5313(14) 0.2927(3) 0.060(2) Uani 1 1 d . . . . .
H5 H 0.1766 0.4522 0.2908 0.072 Uiso 1 1 calc R U . . .
C6 C 0.0468(15) 0.6349(12) 0.3257(3) 0.050(2) Uani 1 1 d . . . . .
C7 C 0.2145(15) 0.6147(12) 0.3579(3) 0.050(2) Uani 1 1 d . . . . .
C8 C 0.3033(16) 0.4777(12) 0.3765(3) 0.055(2) Uani 1 1 d . . . . .
C9 C 0.442(2) 0.5452(13) 0.4090(3) 0.070(3) Uani 1 1 d . . . . .
C10 C 0.428(2) 0.7112(13) 0.4057(3) 0.067(3) Uani 1 1 d . . . . .
C11 C 0.5614(19) 0.4457(17) 0.4431(3) 0.078(3) Uani 1 1 d . . . . .
H11A H 0.5671 0.5150 0.4663 0.094 Uiso 1 1 calc R U . . .
H11B H 0.4772 0.3418 0.4483 0.094 Uiso 1 1 calc R U . . .
C12 C 0.786(2) 0.4079(17) 0.4314(3) 0.080(3) Uani 1 1 d . . . . .
H12A H 0.8728 0.5118 0.4271 0.096 Uiso 1 1 calc R U . . .
H12B H 0.7808 0.3424 0.4076 0.096 Uiso 1 1 calc R U . . .
C13 C 0.2565(19) 0.2941(13) 0.3684(3) 0.067(3) Uani 1 1 d . . . . .
H13A H 0.2398 0.2361 0.3929 0.080 Uiso 1 1 calc R U . . .
H13B H 0.1090 0.2859 0.3544 0.080 Uiso 1 1 calc R U . . .
C14 C 0.429(2) 0.2017(14) 0.3465(3) 0.070(3) Uani 1 1 d . . . . .
H14 H 0.4083 0.0847 0.3441 0.084 Uiso 1 1 calc R U . . .
C15 C 0.605(2) 0.2637(19) 0.3304(4) 0.073(3) Uani 1 1 d . . . . .
H15A H 0.68(2) 0.363(17) 0.330(4) 0.08(4) Uiso 1 1 d . . . . .
H15B H 0.693(18) 0.172(16) 0.320(3) 0.07(3) Uiso 1 1 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
I1 C10 2.079(10) . ?
I2 C12 2.264(12) . ?
O1 C10 1.378(12) . ?
O1 C7 1.378(11) . ?
C1 C2 1.376(17) . ?
C1 C6 1.383(14) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.355(18) . ?
C3 H3 0.9300 . ?
C4 C5 1.398(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.407(13) . ?
C5 H5 0.9300 . ?
C6 C7 1.462(12) . ?
C7 C8 1.349(13) . ?
C8 C9 1.463(13) . ?
C8 C13 1.492(14) . ?
C9 C10 1.310(14) . ?
C9 C11 1.559(15) . ?
C11 C12 1.406(15) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.467(17) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.269(17) . ?
C14 H14 0.9300 . ?
C15 H15A 0.90(13) . ?
C15 H15B 0.96(12) . ?

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
C10 O1 C7 104.2(7) . . ?
C2 C1 C6 122.5(11) . . ?
C2 C1 H1 118.7 . . ?
C6 C1 H1 118.7 . . ?
C1 C2 C3 119.5(11) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 120.4(10) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.4(11) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.4(10) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 116.8(9) . . ?
C1 C6 C7 122.4(9) . . ?
C5 C6 C7 120.8(8) . . ?
C8 C7 O1 111.2(7) . . ?
C8 C7 C6 133.3(9) . . ?
O1 C7 C6 115.3(8) . . ?
C7 C8 C9 105.9(8) . . ?
C7 C8 C13 128.0(8) . . ?
C9 C8 C13 126.0(9) . . ?
C10 C9 C8 105.2(9) . . ?
C10 C9 C11 126.1(10) . . ?
C8 C9 C11 128.5(10) . . ?
C9 C10 O1 113.6(9) . . ?
C9 C10 I1 131.0(8) . . ?
O1 C10 I1 115.4(7) . . ?
C12 C11 C9 106.0(10) . . ?
C12 C11 H11A 110.5 . . ?
C9 C11 H11A 110.5 . . ?
C12 C11 H11B 110.5 . . ?
C9 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
C11 C12 I2 105.8(8) . . ?
C11 C12 H12A 110.6 . . ?
I2 C12 H12A 110.6 . . ?
C11 C12 H12B 110.6 . . ?
I2 C12 H12B 110.6 . . ?
H12A C12 H12B 108.7 . . ?
C14 C13 C8 116.9(10) . . ?
C14 C13 H13A 108.1 . . ?
C8 C13 H13A 108.1 . . ?
C14 C13 H13B 108.1 . . ?
C8 C13 H13B 108.1 . . ?
H13A C13 H13B 107.3 . . ?
C15 C14 C13 127.2(12) . . ?
C15 C14 H14 116.4 . . ?
C13 C14 H14 116.4 . . ?
C14 C15 H15A 138(8) . . ?
C14 C15 H15B 108(7) . . ?
H15A C15 H15B 112(10) . . ?

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 -0.7(19) . . . . ?
C1 C2 C3 C4 -1(2) . . . . ?
C2 C3 C4 C5 2.1(19) . . . . ?
C3 C4 C5 C6 -1.5(17) . . . . ?
C2 C1 C6 C5 1.3(16) . . . . ?
C2 C1 C6 C7 -176.2(10) . . . . ?
C4 C5 C6 C1 -0.2(15) . . . . ?
C4 C5 C6 C7 177.3(9) . . . . ?
C10 O1 C7 C8 1.2(11) . . . . ?
C10 O1 C7 C6 176.2(8) . . . . ?
C1 C6 C7 C8 133.0(12) . . . . ?
C5 C6 C7 C8 -44.4(16) . . . . ?
C1 C6 C7 O1 -40.6(13) . . . . ?
C5 C6 C7 O1 142.0(9) . . . . ?
O1 C7 C8 C9 0.4(11) . . . . ?
C6 C7 C8 C9 -173.4(10) . . . . ?
O1 C7 C8 C13 175.7(10) . . . . ?
C6 C7 C8 C13 1.9(19) . . . . ?
C7 C8 C9 C10 -1.9(13) . . . . ?
C13 C8 C9 C10 -177.3(11) . . . . ?
C7 C8 C9 C11 172.1(11) . . . . ?
C13 C8 C9 C11 -3.3(19) . . . . ?
C8 C9 C10 O1 2.8(14) . . . . ?
C11 C9 C10 O1 -171.4(10) . . . . ?
C8 C9 C10 I1 -176.0(9) . . . . ?
C11 C9 C10 I1 10(2) . . . . ?
C7 O1 C10 C9 -2.6(13) . . . . ?
C7 O1 C10 I1 176.4(7) . . . . ?
C10 C9 C11 C12 -95.7(16) . . . . ?
C8 C9 C11 C12 91.4(14) . . . . ?
C9 C11 C12 I2 -177.7(8) . . . . ?
C7 C8 C13 C14 99.9(13) . . . . ?
C9 C8 C13 C14 -85.7(14) . . . . ?
C8 C13 C14 C15 -7.2(16) . . . . ?

_refine_diff_density_max         1.694
_refine_diff_density_min         -1.261
_refine_diff_density_rms         0.151

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v181055
_database_code_depnum_ccdc_archive 'CCDC 1885449'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2018-12-17 deposited with the CCDC.	2019-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 Br O'
_chemical_formula_weight         305.20

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'
Br Br -0.2901 2.4595 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.1989(4)
_cell_length_b                   7.7847(3)
_cell_length_c                   31.7495(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2767.92(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    4868
_cell_measurement_theta_min      4.451
_cell_measurement_theta_max      54.760

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    2.956
_shelx_estimated_absorpt_T_min   0.589
_shelx_estimated_absorpt_T_max   0.737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4528
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(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            12584
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.566
_diffrn_reflns_theta_max         25.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2711
_reflns_number_gt                2095
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0328P)²+2.3673P] 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     SHELXL
_refine_ls_extinction_coef       0.0022(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2711
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
Br1 Br 0.35588(3) 0.42312(4) 0.17785(2) 0.04888(16) Uani 1 1 d . . . . .
O1 O 0.6002(2) 0.1403(3) 0.45768(7) 0.0596(7) Uani 1 1 d . . . . .
C1 C 0.3893(2) 0.2148(3) 0.36403(8) 0.0272(6) Uani 1 1 d . . . . .
C2 C 0.3349(3) 0.0590(4) 0.38606(8) 0.0384(7) Uani 1 1 d . . . . .
H2A H 0.3628 -0.0530 0.3751 0.046 Uiso 1 1 calc R U . . .
H2B H 0.2468 0.0625 0.3886 0.046 Uiso 1 1 calc R U . . .
C3 C 0.4032(3) 0.1228(3) 0.42613(8) 0.0317(6) Uani 1 1 d . . . . .
C4 C 0.4449(2) 0.2702(3) 0.39916(8) 0.0263(6) Uani 1 1 d . . . . .
C5 C 0.5387(3) 0.3846(4) 0.41439(9) 0.0335(6) Uani 1 1 d . . . . .
C6 C 0.5662(4) 0.5567(4) 0.39678(11) 0.0580(10) Uani 1 1 d . . . . .
H6A H 0.5147 0.6002 0.3738 0.070 Uiso 1 1 calc R U . . .
H6B H 0.6511 0.5909 0.3948 0.070 Uiso 1 1 calc R U . . .
C7 C 0.5119(4) 0.5413(4) 0.44016(11) 0.0559(9) Uani 1 1 d . . . . .
H7A H 0.5637 0.5655 0.4647 0.067 Uiso 1 1 calc R U . . .
H7B H 0.4272 0.5748 0.4437 0.067 Uiso 1 1 calc R U . . .
C8 C 0.6404(3) 0.2710(5) 0.42874(11) 0.0574(10) Uani 1 1 d . . . . .
H8A H 0.6774 0.2156 0.4039 0.069 Uiso 1 1 calc R U . . .
H8B H 0.7020 0.3425 0.4426 0.069 Uiso 1 1 calc R U . . .
C9 C 0.5141(4) 0.0228(4) 0.43873(10) 0.0513(9) Uani 1 1 d . . . . .
H9A H 0.4925 -0.0682 0.4592 0.062 Uiso 1 1 calc R U . . .
H9B H 0.5496 -0.0326 0.4136 0.062 Uiso 1 1 calc R U . . .
C10 C 0.3267(3) 0.1691(4) 0.46396(9) 0.0439(8) Uani 1 1 d . . . . .
H10A H 0.3745 0.2348 0.4842 0.066 Uiso 1 1 calc R U . . .
H10B H 0.2976 0.0637 0.4774 0.066 Uiso 1 1 calc R U . . .
H10C H 0.2586 0.2385 0.4547 0.066 Uiso 1 1 calc R U . . .
C11 C 0.3829(2) 0.2672(3) 0.31967(7) 0.0264(6) Uani 1 1 d . . . . .
C12 C 0.2875(2) 0.2128(3) 0.29493(8) 0.0293(6) Uani 1 1 d . . . . .
H12 H 0.2270 0.1428 0.3070 0.035 Uiso 1 1 calc R U . . .
C13 C 0.2794(3) 0.2594(3) 0.25295(8) 0.0319(6) Uani 1 1 d . . . . .
H13 H 0.2136 0.2225 0.2364 0.038 Uiso 1 1 calc R U . . .
C14 C 0.3673(2) 0.3594(3) 0.23557(8) 0.0288(6) Uani 1 1 d . . . . .
C15 C 0.4642(3) 0.4149(4) 0.25878(9) 0.0339(6) Uani 1 1 d . . . . .
H15 H 0.5246 0.4838 0.2463 0.041 Uiso 1 1 calc R U . . .
C16 C 0.4712(2) 0.3674(4) 0.30105(9) 0.0314(6) Uani 1 1 d . . . . .
H16 H 0.5374 0.4041 0.3174 0.038 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 C14 1.903(2) . ?
O1 C8 1.443(4) . ?
O1 C9 1.459(4) . ?
C1 C4 1.348(4) . ?
C1 C11 1.468(3) . ?
C1 C2 1.527(4) . ?
C2 C3 1.565(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.506(4) . ?
C3 C10 1.519(4) . ?
C3 C9 1.519(5) . ?
C4 C5 1.459(4) . ?
C5 C6 1.484(4) . ?
C5 C7 1.499(4) . ?
C5 C8 1.512(4) . ?
C6 C7 1.510(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.391(4) . ?
C11 C12 1.393(4) . ?
C12 C13 1.384(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.371(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(4) . ?
C15 C16 1.394(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

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
C8 O1 C9 112.7(2) . . ?
C4 C1 C11 136.6(2) . . ?
C4 C1 C2 93.4(2) . . ?
C11 C1 C2 129.9(2) . . ?
C1 C2 C3 85.7(2) . . ?
C1 C2 H2A 114.4 . . ?
C3 C2 H2A 114.4 . . ?
C1 C2 H2B 114.4 . . ?
C3 C2 H2B 114.4 . . ?
H2A C2 H2B 111.5 . . ?
C4 C3 C10 116.4(2) . . ?
C4 C3 C9 106.7(3) . . ?
C10 C3 C9 112.0(2) . . ?
C4 C3 C2 86.06(19) . . ?
C10 C3 C2 116.3(3) . . ?
C9 C3 C2 116.8(2) . . ?
C1 C4 C5 143.3(3) . . ?
C1 C4 C3 94.8(2) . . ?
C5 C4 C3 120.0(2) . . ?
C4 C5 C6 125.1(3) . . ?
C4 C5 C7 122.3(3) . . ?
C6 C5 C7 60.8(2) . . ?
C4 C5 C8 106.6(2) . . ?
C6 C5 C8 119.0(3) . . ?
C7 C5 C8 117.5(3) . . ?
C5 C6 C7 60.1(2) . . ?
C5 C6 H6A 117.8 . . ?
C7 C6 H6A 117.8 . . ?
C5 C6 H6B 117.8 . . ?
C7 C6 H6B 117.8 . . ?
H6A C6 H6B 114.9 . . ?
C5 C7 C6 59.1(2) . . ?
C5 C7 H7A 117.9 . . ?
C6 C7 H7A 117.9 . . ?
C5 C7 H7B 117.9 . . ?
C6 C7 H7B 117.9 . . ?
H7A C7 H7B 115.0 . . ?
O1 C8 C5 111.7(3) . . ?
O1 C8 H8A 109.3 . . ?
C5 C8 H8A 109.3 . . ?
O1 C8 H8B 109.3 . . ?
C5 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
O1 C9 C3 109.1(2) . . ?
O1 C9 H9A 109.9 . . ?
C3 C9 H9A 109.9 . . ?
O1 C9 H9B 109.9 . . ?
C3 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 118.4(2) . . ?
C16 C11 C1 122.0(2) . . ?
C12 C11 C1 119.6(2) . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 119.3(3) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 121.8(2) . . ?
C13 C14 Br1 119.2(2) . . ?
C15 C14 Br1 119.0(2) . . ?
C14 C15 C16 118.3(3) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C11 C16 C15 121.2(3) . . ?
C11 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?

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
C4 C1 C2 C3 -1.5(2) . . . . ?
C11 C1 C2 C3 175.4(3) . . . . ?
C1 C2 C3 C4 1.3(2) . . . . ?
C1 C2 C3 C10 118.9(3) . . . . ?
C1 C2 C3 C9 -105.4(3) . . . . ?
C11 C1 C4 C5 -13.0(7) . . . . ?
C2 C1 C4 C5 163.6(4) . . . . ?
C11 C1 C4 C3 -175.0(3) . . . . ?
C2 C1 C4 C3 1.5(2) . . . . ?
C10 C3 C4 C1 -118.9(3) . . . . ?
C9 C3 C4 C1 115.3(2) . . . . ?
C2 C3 C4 C1 -1.5(2) . . . . ?
C10 C3 C4 C5 73.3(3) . . . . ?
C9 C3 C4 C5 -52.4(3) . . . . ?
C2 C3 C4 C5 -169.2(3) . . . . ?
C1 C4 C5 C6 37.4(6) . . . . ?
C3 C4 C5 C6 -163.4(3) . . . . ?
C1 C4 C5 C7 112.2(4) . . . . ?
C3 C4 C5 C7 -88.5(4) . . . . ?
C1 C4 C5 C8 -108.5(4) . . . . ?
C3 C4 C5 C8 50.7(3) . . . . ?
C4 C5 C6 C7 110.7(3) . . . . ?
C8 C5 C6 C7 -107.2(3) . . . . ?
C4 C5 C7 C6 -115.3(3) . . . . ?
C8 C5 C7 C6 109.6(3) . . . . ?
C9 O1 C8 C5 62.3(4) . . . . ?
C4 C5 C8 O1 -52.0(3) . . . . ?
C6 C5 C8 O1 159.7(3) . . . . ?
C7 C5 C8 O1 89.6(3) . . . . ?
C8 O1 C9 C3 -62.7(3) . . . . ?
C4 C3 C9 O1 53.2(3) . . . . ?
C10 C3 C9 O1 -75.2(3) . . . . ?
C2 C3 C9 O1 147.3(2) . . . . ?
C4 C1 C11 C16 21.7(5) . . . . ?
C2 C1 C11 C16 -153.8(3) . . . . ?
C4 C1 C11 C12 -159.6(3) . . . . ?
C2 C1 C11 C12 24.9(4) . . . . ?
C16 C11 C12 C13 -1.0(4) . . . . ?
C1 C11 C12 C13 -179.7(2) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
C12 C13 C14 Br1 180.0(2) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
Br1 C14 C15 C16 179.9(2) . . . . ?
C12 C11 C16 C15 0.9(4) . . . . ?
C1 C11 C16 C15 179.5(3) . . . . ?
C14 C15 C16 C11 -0.3(4) . . . . ?

_refine_diff_density_max         0.792
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.059

_shelxl_version_number           2013-4

