# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_tx7035a
_database_code_depnum_ccdc_archive 'CCDC 2131745'
loop_
_audit_author_name
_audit_author_address
'Huixin Qiu'
;Qingdao University of Science and Technology
China
;
_audit_update_record             
;
2021-12-30 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
_audit_creation_date             2021-08-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C13 H15 Br O3)'
_chemical_formula_sum            'C26 H30 Br2 O6'
_chemical_formula_weight         598.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHOBr
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.17910(10)
_cell_length_b                   15.1836(2)
_cell_length_c                   14.4771(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.5570(10)
_cell_angle_gamma                90
_cell_volume                     1351.87(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12167
_cell_measurement_temperature    170.01(10)
_cell_measurement_theta_max      75.1580
_cell_measurement_theta_min      3.0300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16499
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.203
_diffrn_reflns_theta_min         3.067
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.01(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 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -100.00 -66.00   0.50    0.05    --  -47.45 -80.00  25.00   68
  2  ω    -71.00  20.00   0.50    0.05    --  -47.45  80.00 149.00  182
  3  ω    -21.00  38.00   0.50    0.05    --   47.45 -80.00  25.00  118
  4  ω     41.00  71.00   0.50    0.05    --   47.45 -80.00  25.00   60
  5  ω   -133.00-107.00   0.50    0.05    --  -99.00 -80.00  25.00   52
  6  ω    108.00 135.00   0.50    0.05    --  103.25  80.00 149.00   54
  7  ω     33.00  79.00   0.50    0.05    --  103.25 -80.00  25.00   92
  8  ω   -113.00 -75.00   0.50    0.05    --  -47.45-125.00-180.00   76
  9  ω    -18.00   8.00   0.50    0.05    --  -47.45  19.00 120.00   52
 10  ω    -26.00   0.00   0.50    0.05    --  -47.45  38.00 -90.00   52
 11  ω   -120.00 -95.00   0.50    0.05    --  -47.45-125.00  30.00   50
 12  ω    -20.00  22.00   0.50    0.05    --  -47.45  19.00  90.00   84
 13  ω    -20.00  27.00   0.50    0.05    --  -47.45  19.00  30.00   94
 14  ω    -22.00  25.00   0.50    0.05    --  -47.45  19.00 150.00   94
 15  ω   -168.00 -97.00   0.50    0.05    --  -99.00 -30.00 120.00  142
 16  ω    -67.00 -30.00   0.50    0.05    --  -99.00  61.00  60.00   74
 17  ω   -166.00 -83.00   0.50    0.05    --  -99.00 -61.00  60.00  166
 18  ω   -140.00 -94.00   0.50    0.05    --  -99.00 -30.00 -90.00   92
 19  ω   -120.00 -94.00   0.50    0.05    --  -99.00 -77.00-120.00   52
 20  ω    -68.00 -43.00   0.50    0.05    --  -99.00  61.00 150.00   50
 21  ω    -99.00 -74.00   0.50    0.05    --  -99.00  80.00 149.00   50
 22  ω    -59.00 -34.00   0.50    0.05    --  -99.00  61.00 120.00   50
 23  ω   -168.00 -87.00   0.50    0.05    --  -99.00 -45.00  90.00  162
 24  ω   -168.00-122.00   0.50    0.05    --  -99.00 -77.00-120.00   92
 25  ω    100.00 167.00   0.50    0.05    --  103.25  30.00-180.00  134
 26  ω     32.00  71.00   0.50    0.05    --  103.25-125.00  90.00   78
 27  ω     70.00 108.00   0.50    0.05    --  103.25-125.00 120.00   76
 28  ω     33.00  63.00   0.50    0.05    --  103.25-125.00 120.00   60
 29  ω     35.00 108.00   0.50    0.05    --  103.25-125.00-180.00  146
 30  ω    114.00 152.00   0.50    0.05    --  103.25  45.00  60.00   76
 31  ω     31.00  57.00   0.50    0.05    --  103.25 -61.00-150.00   52
 32  ω     93.00 145.00   0.50    0.05    --  103.25  15.00 -90.00  104
 33  ω     33.00  96.00   0.50    0.05    --  103.25 -77.00  60.00  126
 34  ω     36.00  61.00   0.50    0.05    --  103.25 -61.00 -60.00   50
 35  ω     88.00 167.00   0.50    0.05    --  103.25  61.00 -90.00  158
 36  ω     81.00 108.00   0.50    0.05    --  103.25-125.00  90.00   54
 37  ω     92.00 168.00   0.50    0.05    --  103.25  45.00-150.00  152
 38  ω     38.00  73.00   0.50    0.05    --  103.25 -61.00-120.00   70
 39  ω     38.00  67.00   0.50    0.05    --  103.25-125.00 150.00   58
 40  ω    102.00 168.00   0.50    0.05    --  103.25  15.00 150.00  132
 41  ω     31.00  73.00   0.50    0.05    --  103.25 -61.00-180.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0025118000
_diffrn_orient_matrix_UB_12      0.0039977000
_diffrn_orient_matrix_UB_13      -0.1062323000
_diffrn_orient_matrix_UB_21      0.1285254000
_diffrn_orient_matrix_UB_22      0.0870717000
_diffrn_orient_matrix_UB_23      0.0094647000
_diffrn_orient_matrix_UB_31      0.2149410000
_diffrn_orient_matrix_UB_32      -0.0519516000
_diffrn_orient_matrix_UB_33      0.0076339000
_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              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.886
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.936
_reflns_number_gt                5186
_reflns_number_total             5343
_reflns_odcompleteness_completeness 99.96
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 2353 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(8)
_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     334
_refine_ls_number_reflns         5343
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0304
_refine_ls_restrained_S_all      1.099
_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)+(0.0530P)²+0.2498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0872
_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. Others
 Sof(H11B)=Sof(C12B)=Sof(H12D)=Sof(H12E)=Sof(H12F)=Sof(C13B)=Sof(H13D)=
 Sof(H13E)=Sof(H13F)=1-FVAR(1)
 Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(H12B)=Sof(H12C)=Sof(C13A)=Sof(H13A)=
 Sof(H13B)=Sof(H13C)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11), C9A(H9A), C11A(H11A), C11A(H11B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C2A(H2A), C3A(H3A), C5A(H5A),
 C6A(H6A), C7A(H7A), C8A(H8A)
3.c Idealised Me refined as rotating group:
 C12(H12G,H12H,H12I), C13(H13G,H13H,H13I), C12A(H12A,H12B,H12C), C13A(H13A,
 H13B,H13C), C12B(H12D,H12E,H12F), C13B(H13D,H13E,H13F)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1A(H1A)
;
_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 -0.58337(8) 0.64697(4) -0.01406(3) 0.06411(16) Uani 1 1 d . . . . .
O1 O 0.3619(4) 0.67375(14) 0.49855(19) 0.0373(5) Uani 1 1 d . . . . .
H1 H 0.381816 0.621387 0.488379 0.056 Uiso 1 1 calc R U . . .
O2 O 0.1359(6) 0.55176(18) 0.5990(2) 0.0567(8) Uani 1 1 d . . . . .
O3 O -0.0615(4) 0.66643(14) 0.64049(17) 0.0354(5) Uani 1 1 d . . . . .
C1 C -0.1130(5) 0.6528(2) 0.2599(2) 0.0307(6) Uani 1 1 d . . . . .
C2 C -0.3243(6) 0.6861(2) 0.2566(2) 0.0347(7) Uani 1 1 d . . . . .
H2 H -0.372653 0.710059 0.309997 0.042 Uiso 1 1 calc R U . . .
C3 C -0.4636(6) 0.6842(2) 0.1757(3) 0.0384(7) Uani 1 1 d . . . . .
H3 H -0.603987 0.706484 0.174858 0.046 Uiso 1 1 calc R U . . .
C4 C -0.3906(6) 0.6487(3) 0.0960(2) 0.0409(7) Uani 1 1 d . . . . .
C5 C -0.1828(6) 0.6155(3) 0.0964(3) 0.0411(8) Uani 1 1 d . . . . .
H5 H -0.135542 0.591981 0.042526 0.049 Uiso 1 1 calc R U . . .
C6 C -0.0450(6) 0.6176(2) 0.1779(3) 0.0355(7) Uani 1 1 d . . . . .
H6 H 0.095104 0.595134 0.178163 0.043 Uiso 1 1 calc R U . . .
C7 C 0.0384(5) 0.6565(2) 0.3440(2) 0.0306(6) Uani 1 1 d . . . . .
H7 H 0.183141 0.642904 0.338172 0.037 Uiso 1 1 calc R U . . .
C8 C -0.0135(6) 0.6776(2) 0.4274(2) 0.0352(7) Uani 1 1 d . . . . .
H8 H -0.159900 0.687294 0.433852 0.042 Uiso 1 1 calc R U . . .
C9 C 0.1425(6) 0.6875(2) 0.5129(2) 0.0333(7) Uani 1 1 d . . . . .
H9 H 0.129581 0.748031 0.535124 0.040 Uiso 1 1 calc R U . . .
C10 C 0.0760(6) 0.6263(2) 0.5888(2) 0.0343(7) Uani 1 1 d . . . . .
C11 C -0.1496(6) 0.6145(2) 0.7132(2) 0.0380(7) Uani 1 1 d . . . . .
H11 H -0.180622 0.554566 0.690660 0.046 Uiso 1 1 calc R U . . .
C12 C -0.3575(7) 0.6592(4) 0.7314(3) 0.0612(12) Uani 1 1 d . . . . .
H12G H -0.326801 0.717840 0.753588 0.092 Uiso 1 1 calc R U . . .
H12H H -0.426351 0.626561 0.777268 0.092 Uiso 1 1 calc R U . . .
H12I H -0.452682 0.661643 0.674952 0.092 Uiso 1 1 calc R U . . .
C13 C 0.0129(7) 0.6115(3) 0.7976(3) 0.0502(9) Uani 1 1 d . . . . .
H13G H 0.144470 0.584192 0.781780 0.075 Uiso 1 1 calc R U . . .
H13H H -0.046057 0.577986 0.845547 0.075 Uiso 1 1 calc R U . . .
H13I H 0.043803 0.670300 0.819347 0.075 Uiso 1 1 calc R U . . .
Br1A Br 1.12067(10) 0.36264(5) 1.05269(3) 0.0767(2) Uani 1 1 d . . . . .
O1A O 0.3320(4) 0.31145(15) 0.48552(19) 0.0393(5) Uani 1 1 d . . . . .
H1A H 0.429864 0.275384 0.482700 0.059 Uiso 1 1 calc R U . . .
O2A O 0.5188(6) 0.52082(17) 0.4340(3) 0.0586(8) Uani 1 1 d . . . . .
O3A O 0.6361(5) 0.38942(14) 0.39183(18) 0.0390(5) Uani 1 1 d . . . . .
C1A C 0.6835(6) 0.3993(2) 0.7730(2) 0.0326(6) Uani 1 1 d . . . . .
C2A C 0.8936(6) 0.3643(2) 0.7752(2) 0.0367(7) Uani 1 1 d . . . . .
H2A H 0.947670 0.348356 0.719808 0.044 Uiso 1 1 calc R U . . .
C3A C 1.0220(6) 0.3531(2) 0.8577(3) 0.0408(7) Uani 1 1 d . . . . .
H3A H 1.160968 0.329419 0.858073 0.049 Uiso 1 1 calc R U . . .
C4A C 0.9407(7) 0.3776(3) 0.9404(3) 0.0448(8) Uani 1 1 d . . . . .
C5A C 0.7328(7) 0.4126(3) 0.9404(3) 0.0442(8) Uani 1 1 d . . . . .
H5A H 0.678855 0.428307 0.995876 0.053 Uiso 1 1 calc R U . . .
C6A C 0.6085(6) 0.4235(2) 0.8577(3) 0.0385(7) Uani 1 1 d . . . . .
H6A H 0.470332 0.447778 0.857650 0.046 Uiso 1 1 calc R U . . .
C7A C 0.5416(5) 0.4101(2) 0.6867(2) 0.0347(7) Uani 1 1 d . . . . .
H7A H 0.411949 0.440356 0.690744 0.042 Uiso 1 1 calc R U . . .
C8A C 0.5794(6) 0.3811(2) 0.6029(2) 0.0353(7) Uani 1 1 d . . . . .
H8A H 0.710251 0.352562 0.596353 0.042 Uiso 1 1 calc R U . . .
C9A C 0.4208(6) 0.3922(2) 0.5192(2) 0.0340(7) Uani 1 1 d . . . . .
H9A H 0.300841 0.428665 0.537195 0.041 Uiso 1 1 calc R U . . .
C10A C 0.5280(5) 0.4418(2) 0.4441(2) 0.0333(6) Uani 1 1 d . . . . .
C11A C 0.7402(6) 0.4300(2) 0.3150(3) 0.0393(7) Uani 1 1 d . . . . .
H11A H 0.776661 0.491053 0.332100 0.047 Uiso 0.56(3) 1 calc R U P A 1
H11B H 0.700877 0.492261 0.306993 0.047 Uiso 0.44(3) 1 calc R U P A 2
C12A C 0.946(3) 0.3816(15) 0.3058(11) 0.074(5) Uani 0.56(3) 1 d . . P A 1
H12A H 1.033857 0.381676 0.364323 0.111 Uiso 0.56(3) 1 calc R U P A 1
H12B H 1.024595 0.409925 0.259861 0.111 Uiso 0.56(3) 1 calc R U P A 1
H12C H 0.914038 0.321991 0.287145 0.111 Uiso 0.56(3) 1 calc R U P A 1
C13A C 0.5811(19) 0.4313(11) 0.2329(7) 0.062(4) Uani 0.56(3) 1 d . . P A 1
H13A H 0.541548 0.372013 0.215563 0.092 Uiso 0.56(3) 1 calc R U P A 1
H13B H 0.643664 0.459718 0.182596 0.092 Uiso 0.56(3) 1 calc R U P A 1
H13C H 0.453935 0.463030 0.246988 0.092 Uiso 0.56(3) 1 calc R U P A 1
C12B C 0.975(3) 0.4183(11) 0.3374(15) 0.056(4) Uani 0.44(3) 1 d . . P A 2
H12D H 1.020293 0.448453 0.394308 0.084 Uiso 0.44(3) 1 calc R U P A 2
H12E H 1.050642 0.442088 0.288254 0.084 Uiso 0.44(3) 1 calc R U P A 2
H12F H 1.007219 0.356687 0.344452 0.084 Uiso 0.44(3) 1 calc R U P A 2
C13B C 0.655(3) 0.3735(19) 0.2277(8) 0.074(6) Uani 0.44(3) 1 d . . P A 2
H13D H 0.708595 0.314242 0.235482 0.110 Uiso 0.44(3) 1 calc R U P A 2
H13E H 0.706745 0.398659 0.173062 0.110 Uiso 0.44(3) 1 calc R U P A 2
H13F H 0.499358 0.372984 0.221404 0.110 Uiso 0.44(3) 1 calc R U P A 2


_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 1.894(4) . ?
O1 H1 0.8200 . ?
O1 C9 1.407(4) . ?
O2 C10 1.195(4) . ?
O3 C10 1.333(4) . ?
O3 C11 1.462(4) . ?
C1 C2 1.397(5) . ?
C1 C6 1.403(4) . ?
C1 C7 1.463(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(5) . ?
C4 C5 1.379(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.318(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.500(5) . ?
C9 H9 0.9800 . ?
C9 C10 1.526(5) . ?
C11 H11 0.9800 . ?
C11 C12 1.498(6) . ?
C11 C13 1.505(6) . ?
C12 H12G 0.9600 . ?
C12 H12H 0.9600 . ?
C12 H12I 0.9600 . ?
C13 H13G 0.9600 . ?
C13 H13H 0.9600 . ?
C13 H13I 0.9600 . ?
Br1A C4A 1.892(4) . ?
O1A H1A 0.8200 . ?
O1A C9A 1.412(4) . ?
O2A C10A 1.210(4) . ?
O3A C10A 1.322(4) . ?
O3A C11A 1.473(4) . ?
C1A C2A 1.400(5) . ?
C1A C6A 1.401(5) . ?
C1A C7A 1.465(5) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.379(5) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.394(5) . ?
C4A C5A 1.390(6) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.369(6) . ?
C6A H6A 0.9300 . ?
C7A H7A 0.9300 . ?
C7A C8A 1.332(5) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.492(5) . ?
C9A H9A 0.9800 . ?
C9A C10A 1.526(5) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A C12A 1.489(13) . ?
C11A C13A 1.467(9) . ?
C11A C12B 1.466(17) . ?
C11A C13B 1.575(15) . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?
C13B H13D 0.9600 . ?
C13B H13E 0.9600 . ?
C13B H13F 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
C9 O1 H1 109.5 . . ?
C10 O3 C11 117.4(2) . . ?
C2 C1 C6 117.7(3) . . ?
C2 C1 C7 122.3(3) . . ?
C6 C1 C7 120.0(3) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.6(3) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.1(3) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 Br1 118.4(3) . . ?
C5 C4 Br1 120.5(3) . . ?
C5 C4 C3 121.0(3) . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.3(3) . . ?
C5 C6 H6 119.4 . . ?
C1 C7 H7 117.3 . . ?
C8 C7 C1 125.4(3) . . ?
C8 C7 H7 117.3 . . ?
C7 C8 H8 117.1 . . ?
C7 C8 C9 125.8(3) . . ?
C9 C8 H8 117.1 . . ?
O1 C9 C8 114.5(3) . . ?
O1 C9 H9 107.3 . . ?
O1 C9 C10 110.3(3) . . ?
C8 C9 H9 107.3 . . ?
C8 C9 C10 109.7(3) . . ?
C10 C9 H9 107.3 . . ?
O2 C10 O3 124.7(3) . . ?
O2 C10 C9 124.3(3) . . ?
O3 C10 C9 110.9(3) . . ?
O3 C11 H11 109.6 . . ?
O3 C11 C12 105.6(3) . . ?
O3 C11 C13 109.6(3) . . ?
C12 C11 H11 109.6 . . ?
C12 C11 C13 112.8(4) . . ?
C13 C11 H11 109.6 . . ?
C11 C12 H12G 109.5 . . ?
C11 C12 H12H 109.5 . . ?
C11 C12 H12I 109.5 . . ?
H12G C12 H12H 109.5 . . ?
H12G C12 H12I 109.5 . . ?
H12H C12 H12I 109.5 . . ?
C11 C13 H13G 109.5 . . ?
C11 C13 H13H 109.5 . . ?
C11 C13 H13I 109.5 . . ?
H13G C13 H13H 109.5 . . ?
H13G C13 H13I 109.5 . . ?
H13H C13 H13I 109.5 . . ?
C9A O1A H1A 109.5 . . ?
C10A O3A C11A 117.5(2) . . ?
C2A C1A C6A 117.7(3) . . ?
C2A C1A C7A 122.6(3) . . ?
C6A C1A C7A 119.7(3) . . ?
C1A C2A H2A 119.3 . . ?
C3A C2A C1A 121.4(3) . . ?
C3A C2A H2A 119.3 . . ?
C2A C3A H3A 120.5 . . ?
C2A C3A C4A 119.1(3) . . ?
C4A C3A H3A 120.5 . . ?
C3A C4A Br1A 118.4(3) . . ?
C5A C4A Br1A 120.8(3) . . ?
C5A C4A C3A 120.8(4) . . ?
C4A C5A H5A 120.4 . . ?
C6A C5A C4A 119.1(3) . . ?
C6A C5A H5A 120.4 . . ?
C1A C6A H6A 119.0 . . ?
C5A C6A C1A 121.9(3) . . ?
C5A C6A H6A 119.0 . . ?
C1A C7A H7A 116.7 . . ?
C8A C7A C1A 126.6(3) . . ?
C8A C7A H7A 116.7 . . ?
C7A C8A H8A 118.6 . . ?
C7A C8A C9A 122.8(3) . . ?
C9A C8A H8A 118.6 . . ?
O1A C9A C8A 112.6(3) . . ?
O1A C9A H9A 107.6 . . ?
O1A C9A C10A 111.3(3) . . ?
C8A C9A H9A 107.6 . . ?
C8A C9A C10A 109.8(3) . . ?
C10A C9A H9A 107.6 . . ?
O2A C10A O3A 123.2(3) . . ?
O2A C10A C9A 123.8(3) . . ?
O3A C10A C9A 113.0(3) . . ?
O3A C11A H11A 108.2 . . ?
O3A C11A H11B 111.8 . . ?
O3A C11A C12A 107.5(5) . . ?
O3A C11A C13B 104.0(6) . . ?
C12A C11A H11A 108.2 . . ?
C13A C11A O3A 108.1(4) . . ?
C13A C11A H11A 108.2 . . ?
C13A C11A C12A 116.5(8) . . ?
C12B C11A O3A 106.1(7) . . ?
C12B C11A H11B 111.8 . . ?
C12B C11A C13B 110.9(9) . . ?
C13B C11A H11B 111.8 . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C11A C13A H13A 109.5 . . ?
C11A C13A H13B 109.5 . . ?
C11A C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C11A C12B H12D 109.5 . . ?
C11A C12B H12E 109.5 . . ?
C11A C12B H12F 109.5 . . ?
H12D C12B H12E 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C11A C13B H13D 109.5 . . ?
C11A C13B H13E 109.5 . . ?
C11A C13B H13F 109.5 . . ?
H13D C13B H13E 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O2A 0.82 1.95 2.717(4) 155.6 . yes
O1A H1A O1 0.82 2.01 2.814(3) 166.3 2_646 yes

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
Br1 C4 C5 C6 -180.0(3) . . . . ?
O1 C9 C10 O2 -38.2(5) . . . . ?
O1 C9 C10 O3 143.3(3) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C1 C7 C8 C9 -175.7(3) . . . . ?
C2 C1 C6 C5 -0.2(5) . . . . ?
C2 C1 C7 C8 11.2(5) . . . . ?
C2 C3 C4 Br1 -179.9(3) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C4 C5 C6 C1 0.0(5) . . . . ?
C6 C1 C2 C3 0.4(5) . . . . ?
C6 C1 C7 C8 -171.0(3) . . . . ?
C7 C1 C2 C3 178.2(3) . . . . ?
C7 C1 C6 C5 -178.1(3) . . . . ?
C7 C8 C9 O1 1.2(5) . . . . ?
C7 C8 C9 C10 -123.5(4) . . . . ?
C8 C9 C10 O2 88.8(5) . . . . ?
C8 C9 C10 O3 -89.6(3) . . . . ?
C10 O3 C11 C12 -156.8(3) . . . . ?
C10 O3 C11 C13 81.5(4) . . . . ?
C11 O3 C10 O2 -1.7(6) . . . . ?
C11 O3 C10 C9 176.7(3) . . . . ?
Br1A C4A C5A C6A 179.1(3) . . . . ?
O1A C9A C10A O2A 141.5(4) . . . . ?
O1A C9A C10A O3A -39.7(4) . . . . ?
C1A C2A C3A C4A -0.4(6) . . . . ?
C1A C7A C8A C9A 177.6(3) . . . . ?
C2A C1A C6A C5A -1.0(5) . . . . ?
C2A C1A C7A C8A 7.6(5) . . . . ?
C2A C3A C4A Br1A -179.4(3) . . . . ?
C2A C3A C4A C5A 0.3(6) . . . . ?
C3A C4A C5A C6A -0.6(6) . . . . ?
C4A C5A C6A C1A 1.0(6) . . . . ?
C6A C1A C2A C3A 0.7(5) . . . . ?
C6A C1A C7A C8A -171.7(3) . . . . ?
C7A C1A C2A C3A -178.6(3) . . . . ?
C7A C1A C6A C5A 178.3(3) . . . . ?
C7A C8A C9A O1A -112.6(4) . . . . ?
C7A C8A C9A C10A 122.8(3) . . . . ?
C8A C9A C10A O2A -93.1(4) . . . . ?
C8A C9A C10A O3A 85.7(3) . . . . ?
C10A O3A C11A C12A 145.1(11) . . . . ?
C10A O3A C11A C13A -88.3(9) . . . . ?
C10A O3A C11A C12B 115.2(9) . . . . ?
C10A O3A C11A C13B -127.8(12) . . . . ?
C11A O3A C10A O2A -3.2(6) . . . . ?
C11A O3A C10A C9A 178.0(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 1.701
_oxdiff_exptl_absorpt_empirical_full_min 0.616
