# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_zhungzhy_0730_auto
_database_code_depnum_ccdc_archive 'CCDC 2431081'
loop_
_audit_author_name
_audit_author_address
'xiao jian'
;south west jiaotong university
China
;
_audit_update_record             
;
2025-03-13 deposited with the CCDC.	2025-05-07 downloaded from the CCDC.
;
_audit_creation_date             2021-07-30
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H22 O3'
_chemical_formula_sum            'C16 H22 O3'
_chemical_formula_weight         262.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_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'
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                   15.7570(2)
_cell_length_b                   10.12180(10)
_cell_length_c                   18.1651(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2897.14(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8658
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      76.9870
_cell_measurement_theta_min      2.8230
_shelx_estimated_absorpt_T_max   0.914
_shelx_estimated_absorpt_T_min   0.870
_exptl_absorpt_coefficient_mu    0.653
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11033
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.413
_diffrn_reflns_theta_min         5.615
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     12.00  84.00   0.50    0.05    --   47.57-116.00 174.00  144
  2  ω     37.00  75.00   0.50    0.05    --  107.75-116.00 174.00   76
  3  ω     35.00  60.00   0.50    0.05    --  107.75 -57.00  60.00   50
  4  ω     58.00  92.00   0.50    0.05    --  107.75 -74.00  58.00   68
  5  ω     36.00  61.00   0.50    0.05    --  107.75 -57.00-120.00   50
  6  ω     49.00  87.00   0.50    0.05    --   47.57 165.00  50.00   76
  7  ω    -29.00  23.00   0.50    0.05    --  -47.57  19.00 -60.00  104
  8  ω    -57.00 -31.00   0.50    0.05    -- -100.00  48.00  35.00   52
  9  ω   -112.00 -63.00   0.50    0.05    -- -100.00 125.00 -30.00   98
 10  ω    -59.00 -31.00   0.50    0.05    -- -100.00 125.00 -30.00   56
 11  ω   -108.00 -39.00   0.50    0.05    -- -100.00 116.00 -96.00  138
 12  ω   -164.00-117.00   0.50    0.05    -- -100.00 -74.00  58.00   94
 13  ω   -112.00 -78.00   0.50    0.05    -- -100.00 -74.00  58.00   68
 14  ω   -152.00-100.00   0.50    0.05    -- -100.00 -99.00-150.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0453242000
_diffrn_orient_matrix_UB_12      0.1170767000
_diffrn_orient_matrix_UB_13      -0.0373513000
_diffrn_orient_matrix_UB_21      0.0363035000
_diffrn_orient_matrix_UB_22      0.0943014000
_diffrn_orient_matrix_UB_23      0.0586756000
_diffrn_orient_matrix_UB_31      0.0785952000
_diffrn_orient_matrix_UB_32      0.0238553000
_diffrn_orient_matrix_UB_33      -0.0485884000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2668
_reflns_number_total             2869
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2869
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0552P)²+1.0798P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1143
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.67370(6) 0.62740(9) 0.41624(5) 0.0342(2) Uani 1 1 d . . . . .
O2 O 0.60140(6) 0.19929(9) 0.50252(5) 0.0345(2) Uani 1 1 d . . . . .
O3 O 0.83903(8) 0.42743(12) 0.65289(7) 0.0546(3) Uani 1 1 d . . . . .
C1 C 0.63543(7) 0.41691(13) 0.46045(7) 0.0262(3) Uani 1 1 d . . . . .
C2 C 0.64165(8) 0.50431(13) 0.40062(7) 0.0272(3) Uani 1 1 d . . . . .
C3 C 0.61644(8) 0.46623(13) 0.33037(7) 0.0287(3) Uani 1 1 d . . . . .
H3 H 0.618553 0.528210 0.291142 0.034 Uiso 1 1 calc R . . . .
C4 C 0.58810(8) 0.33802(13) 0.31697(7) 0.0288(3) Uani 1 1 d . . . . .
C5 C 0.58454(8) 0.24666(13) 0.37435(7) 0.0293(3) Uani 1 1 d . . . . .
C6 C 0.60626(8) 0.28965(13) 0.44492(7) 0.0274(3) Uani 1 1 d . . . . .
C7 C 0.66184(8) 0.45138(13) 0.53843(7) 0.0285(3) Uani 1 1 d . . . . .
H7 H 0.646366 0.373431 0.569482 0.034 Uiso 1 1 calc R . . . .
C8 C 0.75876(8) 0.46577(14) 0.54422(7) 0.0323(3) Uani 1 1 d . . . . .
H8A H 0.786340 0.383793 0.526569 0.039 Uiso 1 1 calc R . . . .
H8B H 0.777908 0.539580 0.512554 0.039 Uiso 1 1 calc R . . . .
C9 C 0.78469(9) 0.49185(14) 0.62250(8) 0.0350(3) Uani 1 1 d . . . . .
C10 C 0.73826(10) 0.60310(15) 0.66026(8) 0.0404(4) Uani 1 1 d . . . . .
H10A H 0.756230 0.688360 0.638578 0.048 Uiso 1 1 calc R . . . .
H10B H 0.753431 0.604020 0.713144 0.048 Uiso 1 1 calc R . . . .
C11 C 0.64201(9) 0.58832(15) 0.65235(7) 0.0360(3) Uani 1 1 d . . . . .
H11A H 0.622733 0.511199 0.681403 0.043 Uiso 1 1 calc R . . . .
H11B H 0.613787 0.667979 0.672365 0.043 Uiso 1 1 calc R . . . .
C12 C 0.61622(8) 0.56987(15) 0.57221(8) 0.0335(3) Uani 1 1 d . . . . .
H12A H 0.630418 0.650570 0.543986 0.040 Uiso 1 1 calc R . . . .
H12B H 0.554104 0.556213 0.569208 0.040 Uiso 1 1 calc R . . . .
C13 C 0.68733(10) 0.71540(15) 0.35625(8) 0.0397(3) Uani 1 1 d . . . . .
H13A H 0.723521 0.672573 0.319437 0.060 Uiso 1 1 calc GR . . . .
H13B H 0.715156 0.795817 0.374144 0.060 Uiso 1 1 calc GR . . . .
H13C H 0.632691 0.738392 0.333886 0.060 Uiso 1 1 calc GR . . . .
C14 C 0.56205(10) 0.29964(16) 0.24003(8) 0.0390(3) Uani 1 1 d . . . . .
H14A H 0.560762 0.378493 0.208749 0.059 Uiso 1 1 calc GR . . . .
H14B H 0.505510 0.259361 0.241275 0.059 Uiso 1 1 calc GR . . . .
H14C H 0.602946 0.236108 0.220059 0.059 Uiso 1 1 calc GR . . . .
C15 C 0.55981(11) 0.10458(15) 0.36085(9) 0.0426(4) Uani 1 1 d . . . . .
H15A H 0.498090 0.098481 0.355123 0.064 Uiso 1 1 calc GR . . . .
H15B H 0.577748 0.050316 0.402732 0.064 Uiso 1 1 calc GR . . . .
H15C H 0.587537 0.072738 0.315937 0.064 Uiso 1 1 calc GR . . . .
C16 C 0.51908(10) 0.19428(16) 0.53499(8) 0.0429(4) Uani 1 1 d . . . . .
H16A H 0.477435 0.167777 0.497744 0.064 Uiso 1 1 calc GR . . . .
H16B H 0.504194 0.281706 0.554248 0.064 Uiso 1 1 calc GR . . . .
H16C H 0.519038 0.129926 0.575296 0.064 Uiso 1 1 calc GR . . . .


_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 C2 1.3740(15) . ?
O1 C13 1.4237(16) . ?
O2 C6 1.3918(15) . ?
O2 C16 1.4259(18) . ?
O3 C9 1.2096(17) . ?
C1 C2 1.4047(17) . ?
C1 C6 1.3965(18) . ?
C1 C7 1.5171(17) . ?
C2 C3 1.3910(18) . ?
C3 C4 1.3938(19) . ?
C4 C5 1.3944(19) . ?
C4 C14 1.5076(18) . ?
C5 C6 1.3964(18) . ?
C5 C15 1.5100(19) . ?
C7 C8 1.5378(17) . ?
C7 C12 1.5270(19) . ?
C8 C9 1.5029(18) . ?
C9 C10 1.508(2) . ?
C10 C11 1.531(2) . ?
C11 C12 1.5229(18) . ?

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 C13 117.70(10) . . ?
C6 O2 C16 112.60(10) . . ?
C2 C1 C7 123.95(11) . . ?
C6 C1 C2 116.59(11) . . ?
C6 C1 C7 119.41(11) . . ?
O1 C2 C1 115.91(11) . . ?
O1 C2 C3 123.07(11) . . ?
C3 C2 C1 121.02(12) . . ?
C2 C3 C4 120.64(12) . . ?
C3 C4 C5 119.99(12) . . ?
C3 C4 C14 119.28(12) . . ?
C5 C4 C14 120.73(12) . . ?
C4 C5 C6 118.01(12) . . ?
C4 C5 C15 121.37(12) . . ?
C6 C5 C15 120.60(12) . . ?
O2 C6 C1 118.19(11) . . ?
O2 C6 C5 118.16(11) . . ?
C5 C6 C1 123.61(12) . . ?
C1 C7 C8 110.98(10) . . ?
C1 C7 C12 115.26(11) . . ?
C12 C7 C8 111.45(11) . . ?
C9 C8 C7 110.57(11) . . ?
O3 C9 C8 121.98(13) . . ?
O3 C9 C10 122.58(13) . . ?
C8 C9 C10 115.45(12) . . ?
C9 C10 C11 111.41(12) . . ?
C12 C11 C10 111.47(12) . . ?
C11 C12 C7 110.78(11) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.513
_oxdiff_exptl_absorpt_empirical_full_min 0.510
####################################################################### 
# 
# 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_220521_s1_lgg
_database_code_depnum_ccdc_archive 'CCDC 2431082'
loop_
_audit_author_name
_audit_author_address
'xiao jian'
;south west jiaotong university
China
;
_audit_update_record             
;
2025-03-13 deposited with the CCDC.	2025-05-07 downloaded from the CCDC.
;
_audit_creation_date             2022-05-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H19 Br O3'
_chemical_formula_sum            'C15 H19 Br O3'
_chemical_formula_weight         327.21
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C190
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   21.8523(12)
_cell_length_b                   5.1108(4)
_cell_length_c                   25.9585(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2899.1(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2528
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.7340
_cell_measurement_theta_min      4.0600
_shelx_estimated_absorpt_T_max   0.537
_shelx_estimated_absorpt_T_min   0.437
_exptl_absorpt_coefficient_mu    2.837
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            14892
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.139
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00 -39.00   0.40   12.50    --  -15.63 139.00  25.00   65
  2  ω     44.00  73.20   0.40   12.50    --   17.66-139.00 -34.00   73
  3  ω    -78.00 -36.00   0.40   12.50    --  -15.63 -57.00-120.00  105
  4  ω    -19.00   8.20   0.40   12.50    --  -15.63 -77.00  60.00   68
  5  ω    -82.00 -38.00   0.40   12.50    --  -15.63 -77.00  60.00  110
  6  ω     35.00  60.20   0.40   12.50    --   17.66 178.00 120.00   63
  7  ω      2.00  75.20   0.40   12.50    --   17.66  57.00  60.00  183
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0024191000
_diffrn_orient_matrix_UB_12      -0.0043941000
_diffrn_orient_matrix_UB_13      -0.0272004000
_diffrn_orient_matrix_UB_21      -0.0323756000
_diffrn_orient_matrix_UB_22      -0.0006070000
_diffrn_orient_matrix_UB_23      0.0020215000
_diffrn_orient_matrix_UB_31      -0.0002330000
_diffrn_orient_matrix_UB_32      0.1388535000
_diffrn_orient_matrix_UB_33      -0.0008380000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    0.874
_reflns_Friedel_fraction_max     0.857
_reflns_number_gt                3989
_reflns_number_total             5527
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 1339 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         5527
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0521
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0211P)²+1.4692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0909
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H14A-H13A
 2.345 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C19(HA), C23(HH), C24(HI), C4(H4), C8(H8), C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C20(HB,HC), C21(HD,HE), C22(HF,HG), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
3.c Idealised Me refined as rotating group:
 C28(HJ,HK,HL), C29(HM,HN,HO), C30(HP,HQ,HR), C13(H13A,H13B,H13C), C14(H14A,
 H14B,H14C), C15(H15A,H15B,H15C)
3.d Idealised tetrahedral OH refined as rotating group:
 O6(H), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br2 Br 0.97135(4) 0.09838(18) 0.68431(3) 0.0664(3) Uani 1 1 d . . . . .
O4 O 0.7391(2) 0.0832(9) 0.56288(18) 0.0428(12) Uani 1 1 d . . . . .
O5 O 0.8546(3) 0.3530(12) 0.7077(2) 0.0713(19) Uani 1 1 d . . . . .
O6 O 0.6236(3) 0.2097(10) 0.5271(2) 0.0600(15) Uani 1 1 d . . . . .
H H 0.632699 0.333576 0.508566 0.090 Uiso 1 1 calc GR . . . .
C16 C 0.8989(3) 0.0852(14) 0.6436(3) 0.0413(17) Uani 1 1 d . . . . .
C17 C 0.8490(4) 0.2303(14) 0.6611(3) 0.0423(19) Uani 1 1 d . . . . .
C18 C 0.7960(3) 0.2246(13) 0.6318(3) 0.0384(17) Uani 1 1 d . . . . .
C19 C 0.7304(3) 0.3146(14) 0.6416(3) 0.0431(19) Uani 1 1 d . . . . .
HA H 0.728825 0.492511 0.655635 0.052 Uiso 1 1 calc R . . . .
C20 C 0.6981(3) 0.1168(16) 0.6769(3) 0.058(2) Uani 1 1 d . . . . .
HB H 0.713011 -0.057806 0.669266 0.069 Uiso 1 1 calc R . . . .
HC H 0.708174 0.155679 0.712501 0.069 Uiso 1 1 calc R . . . .
C21 C 0.6287(4) 0.124(2) 0.6701(3) 0.075(3) Uani 1 1 d . . . . .
HD H 0.609834 -0.005147 0.692517 0.089 Uiso 1 1 calc R . . . .
HE H 0.613232 0.294852 0.679583 0.089 Uiso 1 1 calc R . . . .
C22 C 0.6124(4) 0.0652(16) 0.6146(3) 0.064(2) Uani 1 1 d . . . . .
HF H 0.628414 -0.104891 0.605063 0.076 Uiso 1 1 calc R . . . .
HG H 0.568200 0.060249 0.610897 0.076 Uiso 1 1 calc R . . . .
C23 C 0.6385(3) 0.2713(15) 0.5795(3) 0.050(2) Uani 1 1 d . . . . .
HH H 0.618959 0.438387 0.588043 0.060 Uiso 1 1 calc R . . . .
C24 C 0.7075(3) 0.3039(13) 0.5863(3) 0.0399(17) Uani 1 1 d . . . . .
HI H 0.720197 0.464366 0.568645 0.048 Uiso 1 1 calc R . . . .
C25 C 0.7953(3) 0.0736(13) 0.5875(3) 0.0370(17) Uani 1 1 d . . . . .
C26 C 0.8431(3) -0.0737(14) 0.5694(3) 0.0401(18) Uani 1 1 d . . . . .
C27 C 0.8974(3) -0.0683(14) 0.5992(3) 0.0438(18) Uani 1 1 d . . . . .
C28 C 0.8363(3) -0.2410(16) 0.5220(3) 0.055(2) Uani 1 1 d . . . . .
HJ H 0.866079 -0.189066 0.496792 0.083 Uiso 1 1 calc GR . . . .
HK H 0.795953 -0.219230 0.508058 0.083 Uiso 1 1 calc GR . . . .
HL H 0.842590 -0.421244 0.530947 0.083 Uiso 1 1 calc GR . . . .
C29 C 0.9516(4) -0.2296(17) 0.5832(3) 0.065(2) Uani 1 1 d . . . . .
HM H 0.960654 -0.355486 0.609606 0.098 Uiso 1 1 calc GR . . . .
HN H 0.986389 -0.117420 0.578288 0.098 Uiso 1 1 calc GR . . . .
HO H 0.942538 -0.318875 0.551618 0.098 Uiso 1 1 calc GR . . . .
C30 C 0.8277(4) 0.5929(16) 0.7162(3) 0.069(3) Uani 1 1 d . . . . .
HP H 0.823222 0.683735 0.684062 0.103 Uiso 1 1 calc GR . . . .
HQ H 0.852854 0.694158 0.739023 0.103 Uiso 1 1 calc GR . . . .
HR H 0.788091 0.567837 0.731516 0.103 Uiso 1 1 calc GR . . . .
Br1 Br 0.33811(4) 0.5598(2) 0.30625(4) 0.0800(3) Uani 1 1 d . . . . .
O1 O 0.5598(2) 0.5615(9) 0.44105(19) 0.0430(12) Uani 1 1 d . . . . .
C1 C 0.4075(3) 0.5535(14) 0.3513(3) 0.0433(19) Uani 1 1 d . . . . .
O2 O 0.4523(2) 0.8409(10) 0.29153(19) 0.0585(15) Uani 1 1 d . . . . .
C2 C 0.4568(3) 0.7108(14) 0.3372(3) 0.0387(17) Uani 1 1 d . . . . .
O3 O 0.6689(3) 0.7097(10) 0.48638(19) 0.0582(15) Uani 1 1 d . . . . .
H3 H 0.658026 0.830636 0.504991 0.087 Uiso 1 1 calc GR . . . .
C3 C 0.5076(3) 0.7061(13) 0.3693(3) 0.0346(16) Uani 1 1 d . . . . .
C4 C 0.5729(3) 0.8106(13) 0.3654(3) 0.0360(16) Uani 1 1 d . . . . .
H4 H 0.573758 0.991272 0.352835 0.043 Uiso 1 1 calc R . . . .
C5 C 0.6118(3) 0.6290(15) 0.3318(3) 0.051(2) Uani 1 1 d . . . . .
H5A H 0.599119 0.449431 0.337413 0.061 Uiso 1 1 calc R . . . .
H5B H 0.604719 0.670568 0.295796 0.061 Uiso 1 1 calc R . . . .
C6 C 0.6795(3) 0.6538(17) 0.3433(3) 0.060(2) Uani 1 1 d . . . . .
H6A H 0.692913 0.831104 0.336227 0.072 Uiso 1 1 calc R . . . .
H6B H 0.702420 0.536209 0.321202 0.072 Uiso 1 1 calc R . . . .
C7 C 0.6922(3) 0.5877(16) 0.3993(3) 0.058(2) Uani 1 1 d . . . . .
H7A H 0.678617 0.410691 0.406523 0.070 Uiso 1 1 calc R . . . .
H7B H 0.735806 0.597080 0.405901 0.070 Uiso 1 1 calc R . . . .
C8 C 0.6588(3) 0.7780(15) 0.4339(3) 0.049(2) Uani 1 1 d . . . . .
H8 H 0.676327 0.952095 0.428258 0.059 Uiso 1 1 calc R . . . .
C9 C 0.5909(3) 0.7941(13) 0.4227(3) 0.0393(17) Uani 1 1 d . . . . .
H9 H 0.574048 0.946610 0.440625 0.047 Uiso 1 1 calc R . . . .
C10 C 0.5052(3) 0.5495(13) 0.4130(3) 0.0381(18) Uani 1 1 d . . . . .
C11 C 0.4570(3) 0.3914(13) 0.4270(3) 0.0380(19) Uani 1 1 d . . . . .
C12 C 0.4056(3) 0.3932(14) 0.3944(3) 0.0428(18) Uani 1 1 d . . . . .
C13 C 0.4601(3) 0.2250(16) 0.4750(3) 0.054(2) Uani 1 1 d . . . . .
H13A H 0.455234 0.044211 0.465856 0.080 Uiso 1 1 calc DGR . . . .
H13B H 0.428030 0.275644 0.498206 0.080 Uiso 1 1 calc GR . . . .
H13C H 0.499051 0.249504 0.491407 0.080 Uiso 1 1 calc GR . . . .
C14 C 0.3513(3) 0.2254(18) 0.4076(3) 0.066(2) Uani 1 1 d . . . . .
H14A H 0.365080 0.053484 0.416995 0.099 Uiso 1 1 calc DGR . . . .
H14B H 0.324691 0.213737 0.378322 0.099 Uiso 1 1 calc GR . . . .
H14C H 0.329598 0.301963 0.436013 0.099 Uiso 1 1 calc GR . . . .
C15 C 0.4864(4) 1.0712(15) 0.2836(3) 0.061(2) Uani 1 1 d . . . . .
H15A H 0.469389 1.166775 0.255141 0.091 Uiso 1 1 calc GR . . . .
H15B H 0.528126 1.026525 0.276112 0.091 Uiso 1 1 calc GR . . . .
H15C H 0.484886 1.177313 0.314070 0.091 Uiso 1 1 calc GR . . . .


_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
Br2 C16 1.905(7) . ?
O4 C24 1.456(8) . ?
O4 C25 1.385(8) . ?
O5 C17 1.367(8) . ?
O5 C30 1.378(9) . ?
O6 H 0.8200 . ?
O6 C23 1.432(9) . ?
C16 C17 1.395(10) . ?
C16 C27 1.395(10) . ?
C17 C18 1.385(10) . ?
C18 C19 1.528(9) . ?
C18 C25 1.386(9) . ?
C19 HA 0.9800 . ?
C19 C20 1.536(11) . ?
C19 C24 1.521(9) . ?
C20 HB 0.9700 . ?
C20 HC 0.9700 . ?
C20 C21 1.528(11) . ?
C21 HD 0.9700 . ?
C21 HE 0.9700 . ?
C21 C22 1.513(11) . ?
C22 HF 0.9700 . ?
C22 HG 0.9700 . ?
C22 C23 1.505(11) . ?
C23 HH 0.9800 . ?
C23 C24 1.527(10) . ?
C24 HI 0.9800 . ?
C25 C26 1.371(9) . ?
C26 C27 1.416(10) . ?
C26 C28 1.506(10) . ?
C27 C29 1.501(10) . ?
C28 HJ 0.9600 . ?
C28 HK 0.9600 . ?
C28 HL 0.9600 . ?
C29 HM 0.9600 . ?
C29 HN 0.9600 . ?
C29 HO 0.9600 . ?
C30 HP 0.9600 . ?
C30 HQ 0.9600 . ?
C30 HR 0.9600 . ?
Br1 C1 1.914(7) . ?
O1 C9 1.450(7) . ?
O1 C10 1.398(8) . ?
C1 C2 1.394(9) . ?
C1 C12 1.389(10) . ?
O2 C2 1.364(8) . ?
O2 C15 1.408(9) . ?
C2 C3 1.386(9) . ?
O3 H3 0.8200 . ?
O3 C8 1.423(9) . ?
C3 C4 1.527(9) . ?
C3 C10 1.391(9) . ?
C4 H4 0.9800 . ?
C4 C5 1.533(9) . ?
C4 C9 1.539(9) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.515(10) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.517(11) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.513(10) . ?
C8 H8 0.9800 . ?
C8 C9 1.514(9) . ?
C9 H9 0.9800 . ?
C10 C11 1.376(9) . ?
C11 C12 1.405(10) . ?
C11 C13 1.510(10) . ?
C12 C14 1.503(9) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C25 O4 C24 104.8(5) . . ?
C17 O5 C30 120.8(6) . . ?
C23 O6 H 109.5 . . ?
C17 C16 Br2 116.7(6) . . ?
C27 C16 Br2 119.9(5) . . ?
C27 C16 C17 123.4(7) . . ?
O5 C17 C16 117.5(7) . . ?
O5 C17 C18 124.8(7) . . ?
C18 C17 C16 117.6(7) . . ?
C17 C18 C19 133.4(7) . . ?
C17 C18 C25 118.5(6) . . ?
C25 C18 C19 107.1(6) . . ?
C18 C19 HA 111.9 . . ?
C18 C19 C20 109.3(6) . . ?
C20 C19 HA 111.9 . . ?
C24 C19 C18 98.2(5) . . ?
C24 C19 HA 111.9 . . ?
C24 C19 C20 112.9(7) . . ?
C19 C20 HB 109.3 . . ?
C19 C20 HC 109.3 . . ?
HB C20 HC 107.9 . . ?
C21 C20 C19 111.8(7) . . ?
C21 C20 HB 109.3 . . ?
C21 C20 HC 109.3 . . ?
C20 C21 HD 109.7 . . ?
C20 C21 HE 109.7 . . ?
HD C21 HE 108.2 . . ?
C22 C21 C20 109.9(7) . . ?
C22 C21 HD 109.7 . . ?
C22 C21 HE 109.7 . . ?
C21 C22 HF 109.6 . . ?
C21 C22 HG 109.6 . . ?
HF C22 HG 108.1 . . ?
C23 C22 C21 110.5(7) . . ?
C23 C22 HF 109.6 . . ?
C23 C22 HG 109.6 . . ?
O6 C23 C22 109.6(6) . . ?
O6 C23 HH 107.9 . . ?
O6 C23 C24 111.0(6) . . ?
C22 C23 HH 107.9 . . ?
C22 C23 C24 112.4(6) . . ?
C24 C23 HH 107.9 . . ?
O4 C24 C19 105.4(5) . . ?
O4 C24 C23 109.6(5) . . ?
O4 C24 HI 108.5 . . ?
C19 C24 C23 116.0(6) . . ?
C19 C24 HI 108.5 . . ?
C23 C24 HI 108.5 . . ?
O4 C25 C18 112.0(6) . . ?
C26 C25 O4 122.5(6) . . ?
C26 C25 C18 125.6(7) . . ?
C25 C26 C27 116.1(6) . . ?
C25 C26 C28 121.1(6) . . ?
C27 C26 C28 122.7(6) . . ?
C16 C27 C26 118.8(6) . . ?
C16 C27 C29 121.2(7) . . ?
C26 C27 C29 120.0(7) . . ?
C26 C28 HJ 109.5 . . ?
C26 C28 HK 109.5 . . ?
C26 C28 HL 109.5 . . ?
HJ C28 HK 109.5 . . ?
HJ C28 HL 109.5 . . ?
HK C28 HL 109.5 . . ?
C27 C29 HM 109.5 . . ?
C27 C29 HN 109.5 . . ?
C27 C29 HO 109.5 . . ?
HM C29 HN 109.5 . . ?
HM C29 HO 109.5 . . ?
HN C29 HO 109.5 . . ?
O5 C30 HP 109.5 . . ?
O5 C30 HQ 109.5 . . ?
O5 C30 HR 109.5 . . ?
HP C30 HQ 109.5 . . ?
HP C30 HR 109.5 . . ?
HQ C30 HR 109.5 . . ?
C10 O1 C9 105.4(5) . . ?
C2 C1 Br1 116.3(5) . . ?
C12 C1 Br1 118.6(5) . . ?
C12 C1 C2 125.0(7) . . ?
C2 O2 C15 119.8(6) . . ?
O2 C2 C1 116.9(6) . . ?
O2 C2 C3 126.0(6) . . ?
C3 C2 C1 116.9(6) . . ?
C8 O3 H3 109.5 . . ?
C2 C3 C4 134.7(6) . . ?
C2 C3 C10 118.0(6) . . ?
C10 C3 C4 106.8(6) . . ?
C3 C4 H4 111.7 . . ?
C3 C4 C5 110.1(6) . . ?
C3 C4 C9 99.1(5) . . ?
C5 C4 H4 111.7 . . ?
C5 C4 C9 112.1(6) . . ?
C9 C4 H4 111.7 . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 C4 112.2(6) . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C5 C6 C7 110.4(6) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C6 C7 H7A 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 C6 109.8(6) . . ?
C8 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
O3 C8 C7 109.6(6) . . ?
O3 C8 H8 107.8 . . ?
O3 C8 C9 110.6(6) . . ?
C7 C8 H8 107.8 . . ?
C7 C8 C9 113.1(6) . . ?
C9 C8 H8 107.8 . . ?
O1 C9 C4 104.0(5) . . ?
O1 C9 C8 110.6(5) . . ?
O1 C9 H9 108.6 . . ?
C4 C9 H9 108.6 . . ?
C8 C9 C4 116.1(6) . . ?
C8 C9 H9 108.6 . . ?
C3 C10 O1 111.6(6) . . ?
C11 C10 O1 122.8(6) . . ?
C11 C10 C3 125.5(7) . . ?
C10 C11 C12 116.7(6) . . ?
C10 C11 C13 120.9(7) . . ?
C12 C11 C13 122.4(6) . . ?
C1 C12 C11 117.7(6) . . ?
C1 C12 C14 123.0(7) . . ?
C11 C12 C14 119.3(7) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
Br2 C16 C17 O5 -4.7(9) . . . . ?
Br2 C16 C17 C18 179.6(5) . . . . ?
Br2 C16 C27 C26 -179.7(5) . . . . ?
Br2 C16 C27 C29 1.4(10) . . . . ?
O4 C25 C26 C27 -178.8(6) . . . . ?
O4 C25 C26 C28 -1.8(11) . . . . ?
O5 C17 C18 C19 -7.2(13) . . . . ?
O5 C17 C18 C25 -174.5(7) . . . . ?
O6 C23 C24 O4 -48.8(8) . . . . ?
O6 C23 C24 C19 -168.0(6) . . . . ?
C16 C17 C18 C19 168.1(7) . . . . ?
C16 C17 C18 C25 0.9(10) . . . . ?
C17 C16 C27 C26 1.6(11) . . . . ?
C17 C16 C27 C29 -177.4(7) . . . . ?
C17 C18 C19 C20 -76.6(10) . . . . ?
C17 C18 C19 C24 165.6(8) . . . . ?
C17 C18 C25 O4 178.8(6) . . . . ?
C17 C18 C25 C26 -0.1(11) . . . . ?
C18 C19 C20 C21 -155.5(6) . . . . ?
C18 C19 C24 O4 34.5(7) . . . . ?
C18 C19 C24 C23 156.0(6) . . . . ?
C18 C25 C26 C27 0.1(11) . . . . ?
C18 C25 C26 C28 177.1(7) . . . . ?
C19 C18 C25 O4 8.5(8) . . . . ?
C19 C18 C25 C26 -170.5(7) . . . . ?
C19 C20 C21 C22 58.5(10) . . . . ?
C20 C19 C24 O4 -80.5(7) . . . . ?
C20 C19 C24 C23 40.9(9) . . . . ?
C20 C21 C22 C23 -62.3(9) . . . . ?
C21 C22 C23 O6 178.8(6) . . . . ?
C21 C22 C23 C24 55.0(9) . . . . ?
C22 C23 C24 O4 74.3(8) . . . . ?
C22 C23 C24 C19 -44.9(9) . . . . ?
C24 O4 C25 C18 14.4(7) . . . . ?
C24 O4 C25 C26 -166.6(7) . . . . ?
C24 C19 C20 C21 -47.4(9) . . . . ?
C25 O4 C24 C19 -31.6(7) . . . . ?
C25 O4 C24 C23 -157.1(6) . . . . ?
C25 C18 C19 C20 91.7(7) . . . . ?
C25 C18 C19 C24 -26.1(7) . . . . ?
C25 C26 C27 C16 -0.7(10) . . . . ?
C25 C26 C27 C29 178.2(7) . . . . ?
C27 C16 C17 O5 174.1(7) . . . . ?
C27 C16 C17 C18 -1.7(11) . . . . ?
C28 C26 C27 C16 -177.7(7) . . . . ?
C28 C26 C27 C29 1.3(11) . . . . ?
C30 O5 C17 C16 144.9(8) . . . . ?
C30 O5 C17 C18 -39.8(12) . . . . ?
Br1 C1 C2 O2 -3.7(9) . . . . ?
Br1 C1 C2 C3 -179.4(5) . . . . ?
Br1 C1 C12 C11 180.0(5) . . . . ?
Br1 C1 C12 C14 -0.5(10) . . . . ?
O1 C10 C11 C12 -178.2(6) . . . . ?
O1 C10 C11 C13 1.7(11) . . . . ?
C1 C2 C3 C4 169.6(7) . . . . ?
C1 C2 C3 C10 -0.9(10) . . . . ?
O2 C2 C3 C4 -5.7(13) . . . . ?
O2 C2 C3 C10 -176.2(7) . . . . ?
C2 C1 C12 C11 1.0(12) . . . . ?
C2 C1 C12 C14 -179.5(7) . . . . ?
C2 C3 C4 C5 -78.8(10) . . . . ?
C2 C3 C4 C9 163.6(8) . . . . ?
C2 C3 C10 O1 179.1(6) . . . . ?
C2 C3 C10 C11 1.8(11) . . . . ?
O3 C8 C9 O1 -49.8(8) . . . . ?
O3 C8 C9 C4 -168.0(6) . . . . ?
C3 C4 C5 C6 -156.8(6) . . . . ?
C3 C4 C9 O1 35.1(6) . . . . ?
C3 C4 C9 C8 156.8(6) . . . . ?
C3 C10 C11 C12 -1.1(11) . . . . ?
C3 C10 C11 C13 178.7(7) . . . . ?
C4 C3 C10 O1 6.1(8) . . . . ?
C4 C3 C10 C11 -171.2(7) . . . . ?
C4 C5 C6 C7 59.3(9) . . . . ?
C5 C4 C9 O1 -81.1(6) . . . . ?
C5 C4 C9 C8 40.6(8) . . . . ?
C5 C6 C7 C8 -61.7(9) . . . . ?
C6 C7 C8 O3 177.9(6) . . . . ?
C6 C7 C8 C9 54.0(9) . . . . ?
C7 C8 C9 O1 73.6(8) . . . . ?
C7 C8 C9 C4 -44.6(9) . . . . ?
C9 O1 C10 C3 17.5(7) . . . . ?
C9 O1 C10 C11 -165.1(7) . . . . ?
C9 C4 C5 C6 -47.6(8) . . . . ?
C10 O1 C9 C4 -33.3(6) . . . . ?
C10 O1 C9 C8 -158.6(6) . . . . ?
C10 C3 C4 C5 92.5(7) . . . . ?
C10 C3 C4 C9 -25.1(7) . . . . ?
C10 C11 C12 C1 -0.2(10) . . . . ?
C10 C11 C12 C14 -179.8(7) . . . . ?
C12 C1 C2 O2 175.3(7) . . . . ?
C12 C1 C2 C3 -0.4(12) . . . . ?
C13 C11 C12 C1 180.0(7) . . . . ?
C13 C11 C12 C14 0.4(11) . . . . ?
C15 O2 C2 C1 155.6(7) . . . . ?
C15 O2 C2 C3 -29.1(11) . . . . ?

_olex2_date_sample_data_collection 2022-05-21
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.584
_oxdiff_exptl_absorpt_empirical_full_min 0.691
####################################################################### 
# 
# 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_zhuangzhy_1216-2_auto
_database_code_depnum_ccdc_archive 'CCDC 2431083'
loop_
_audit_author_name
_audit_author_address
'xiao jian'
;south west jiaotong university
China
;
_audit_update_record             
;
2025-03-13 deposited with the CCDC.	2025-05-07 downloaded from the CCDC.
;
_audit_creation_date             2021-12-16
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H17 Br O3'
_chemical_formula_sum            'C15 H17 Br O3'
_chemical_formula_weight         325.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   9.81899(16)
_cell_length_b                   9.17658(16)
_cell_length_c                   15.2660(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.9390(17)
_cell_angle_gamma                90
_cell_volume                     1345.78(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7196
_cell_measurement_temperature    149.97(10)
_cell_measurement_theta_max      76.9140
_cell_measurement_theta_min      4.6020
_shelx_estimated_absorpt_T_max   0.634
_shelx_estimated_absorpt_T_min   0.592
_exptl_absorpt_coefficient_mu    4.182
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull light colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8763
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.451
_diffrn_reflns_theta_min         4.932
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.97(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     87.00 112.00   0.50    0.11    --  107.75  77.00   0.00   50
  2  ω    104.00 130.00   0.50    0.11    --  107.75 111.00  28.00   52
  3  ω    123.00 174.00   0.50    0.11    --  107.75  77.00   0.00  102
  4  ω    104.00 169.00   0.50    0.11    --  107.75  37.00   0.00  130
  5  ω    -22.00  38.00   0.50    0.05    --   47.57 -37.00-180.00  120
  6  ω      7.00  38.00   0.50    0.05    --   47.57-111.00 -64.00   62
  7  ω     45.00  82.00   0.50    0.05    --   47.57-111.00 -64.00   74
  8  ω    -26.00  21.00   0.50    0.05    --   47.57 -19.00  30.00   94
  9  ω    -27.00  -2.00   0.50    0.05    --   47.57 -19.00 120.00   50
 10  ω     35.00 108.00   0.50    0.11    --  107.75-111.00 -64.00  146
 11  ω     70.00 102.00   0.50    0.11    --  107.75 -77.00 -60.00   64
 12  ω     38.00  66.00   0.50    0.11    --  107.75 -77.00 -60.00   56
 13  ω     35.00  60.00   0.50    0.11    --  107.75 -57.00 -90.00   50
 14  ω     37.00  62.00   0.50    0.11    --  107.75 -57.00 -60.00   50
 15  ω     38.00  63.00   0.50    0.11    --  107.75 -57.00   0.00   50
 16  ω     35.00  60.00   0.50    0.11    --  107.75 -57.00 120.00   50
 17  ω    -20.00  27.00   0.50    0.05    --  -47.57  19.00   0.00   94
 18  ω    -43.00  23.00   0.50    0.05    --  -47.57  37.00-120.00  132
 19  ω    -57.00 -28.00   0.50    0.11    -- -100.00  57.00-150.00   58
 20  ω    -66.00 -27.00   0.50    0.11    -- -100.00  57.00-120.00   78
 21  ω    -69.00 -29.00   0.50    0.11    -- -100.00  57.00   0.00   80
 22  ω    -53.00 -27.00   0.50    0.11    -- -100.00  57.00  60.00   52
 23  ω    -51.00 -26.00   0.50    0.05    --  -47.57 111.00  28.00   50
 24  ω   -106.00 -52.00   0.50    0.11    -- -100.00 111.00  28.00  108
 25  ω   -125.00 -94.00   0.50    0.11    -- -100.00 -57.00 150.00   62
 26  ω   -146.00 -90.00   0.50    0.11    -- -100.00-111.00 -64.00  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0415621000
_diffrn_orient_matrix_UB_12      0.1564354000
_diffrn_orient_matrix_UB_13      0.0313147000
_diffrn_orient_matrix_UB_21      0.0275410000
_diffrn_orient_matrix_UB_22      -0.0510777000
_diffrn_orient_matrix_UB_23      0.0981723000
_diffrn_orient_matrix_UB_31      0.1524132000
_diffrn_orient_matrix_UB_32      -0.0333619000
_diffrn_orient_matrix_UB_33      -0.0038866000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2555
_reflns_number_total             2711
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.892
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2711
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0509P)²+2.5401P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1189
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C12(H12A,H12B), C14(H14A,H14B)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.80895(4) 0.08097(4) 0.51066(3) 0.04470(17) Uani 1 1 d . . . . .
O1 O 0.5922(2) 0.1929(2) 0.35838(15) 0.0306(5) Uani 1 1 d . . . . .
O2 O 0.6570(3) 0.7072(2) 0.41936(15) 0.0328(5) Uani 1 1 d . . . . .
O3 O 0.3528(3) 0.8325(3) 0.29400(19) 0.0431(6) Uani 1 1 d . . . . .
C1 C 0.8332(3) 0.3924(4) 0.5360(2) 0.0304(7) Uani 1 1 d . . . . .
C2 C 0.6601(3) 0.3071(3) 0.4077(2) 0.0254(6) Uani 1 1 d . . . . .
C3 C 0.6242(3) 0.4497(3) 0.38136(19) 0.0243(6) Uani 1 1 d . . . . .
C4 C 0.7632(3) 0.2795(4) 0.4831(2) 0.0286(6) Uani 1 1 d . . . . .
C5 C 0.6926(3) 0.5626(3) 0.43492(19) 0.0246(6) Uani 1 1 d . . . . .
C6 C 0.5931(3) 0.7615(4) 0.3318(2) 0.0304(7) Uani 1 1 d . . . . .
H6 H 0.609167 0.868991 0.330711 0.036 Uiso 1 1 calc R . . . .
C7 C 0.5156(3) 0.4784(4) 0.2967(2) 0.0300(7) Uani 1 1 d . . . . .
H7 H 0.474373 0.382847 0.273479 0.036 Uiso 1 1 calc R . . . .
C8 C 0.3980(3) 0.5764(4) 0.3136(2) 0.0328(7) Uani 1 1 d . . . . .
H8A H 0.313687 0.558784 0.266630 0.039 Uiso 1 1 calc R . . . .
H8B H 0.375881 0.551353 0.372130 0.039 Uiso 1 1 calc R . . . .
C9 C 0.7959(3) 0.5361(4) 0.5111(2) 0.0289(7) Uani 1 1 d . . . . .
C10 C 0.4367(3) 0.7341(4) 0.3133(2) 0.0310(7) Uani 1 1 d . . . . .
C11 C 0.8661(4) 0.6635(4) 0.5653(2) 0.0364(8) Uani 1 1 d . . . . .
H11A H 0.842833 0.662781 0.624667 0.055 Uiso 1 1 calc GR . . . .
H11B H 0.833824 0.754771 0.534589 0.055 Uiso 1 1 calc GR . . . .
H11C H 0.967206 0.655338 0.571618 0.055 Uiso 1 1 calc GR . . . .
C12 C 0.6531(3) 0.6915(4) 0.2574(2) 0.0371(8) Uani 1 1 d . . . . .
H12A H 0.753731 0.673697 0.279643 0.045 Uiso 1 1 calc R . . . .
H12B H 0.642897 0.760127 0.206425 0.045 Uiso 1 1 calc R . . . .
C13 C 0.4685(4) 0.1515(4) 0.3892(3) 0.0420(8) Uani 1 1 d . . . . .
H13A H 0.423820 0.069088 0.353619 0.063 Uiso 1 1 calc GR . . . .
H13B H 0.403935 0.234056 0.382585 0.063 Uiso 1 1 calc GR . . . .
H13C H 0.493692 0.123054 0.452380 0.063 Uiso 1 1 calc GR . . . .
C14 C 0.5820(4) 0.5478(4) 0.2245(2) 0.0371(8) Uani 1 1 d . . . . .
H14A H 0.651399 0.479986 0.208542 0.044 Uiso 1 1 calc R . . . .
H14B H 0.509443 0.565720 0.170121 0.044 Uiso 1 1 calc R . . . .
C15 C 0.9428(4) 0.3604(5) 0.6183(2) 0.0426(9) Uani 1 1 d . . . . .
H15A H 0.903277 0.298097 0.658855 0.064 Uiso 1 1 calc GR . . . .
H15B H 0.975136 0.451944 0.648614 0.064 Uiso 1 1 calc GR . . . .
H15C H 1.021322 0.310295 0.600958 0.064 Uiso 1 1 calc GR . . . .


_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 C4 1.902(3) . ?
O1 C2 1.379(4) . ?
O1 C13 1.441(4) . ?
O2 C5 1.380(4) . ?
O2 C6 1.442(4) . ?
O3 C10 1.217(4) . ?
C1 C4 1.402(5) . ?
C1 C9 1.400(5) . ?
C1 C15 1.504(4) . ?
C2 C3 1.393(4) . ?
C2 C4 1.390(4) . ?
C3 C5 1.402(4) . ?
C3 C7 1.518(4) . ?
C5 C9 1.397(4) . ?
C6 C10 1.524(4) . ?
C6 C12 1.525(5) . ?
C7 C8 1.527(5) . ?
C7 C14 1.530(5) . ?
C8 C10 1.496(5) . ?
C9 C11 1.513(5) . ?
C12 C14 1.527(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
C2 O1 C13 111.5(2) . . ?
C5 O2 C6 122.5(2) . . ?
C4 C1 C15 121.1(3) . . ?
C9 C1 C4 118.1(3) . . ?
C9 C1 C15 120.8(3) . . ?
O1 C2 C3 119.4(3) . . ?
O1 C2 C4 120.1(3) . . ?
C4 C2 C3 120.5(3) . . ?
C2 C3 C5 117.6(3) . . ?
C2 C3 C7 120.0(3) . . ?
C5 C3 C7 122.4(3) . . ?
C1 C4 Br1 121.0(2) . . ?
C2 C4 Br1 117.1(3) . . ?
C2 C4 C1 121.9(3) . . ?
O2 C5 C3 122.4(3) . . ?
O2 C5 C9 115.2(3) . . ?
C9 C5 C3 122.3(3) . . ?
O2 C6 C10 110.1(3) . . ?
O2 C6 C12 112.6(3) . . ?
C10 C6 C12 108.8(3) . . ?
C3 C7 C8 112.4(3) . . ?
C3 C7 C14 110.9(3) . . ?
C8 C7 C14 109.0(3) . . ?
C10 C8 C7 111.6(3) . . ?
C1 C9 C11 121.0(3) . . ?
C5 C9 C1 119.6(3) . . ?
C5 C9 C11 119.4(3) . . ?
O3 C10 C6 121.9(3) . . ?
O3 C10 C8 124.0(3) . . ?
C8 C10 C6 113.9(3) . . ?
C6 C12 C14 112.8(3) . . ?
C12 C14 C7 110.9(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.470
_oxdiff_exptl_absorpt_empirical_full_min 0.370
