# 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_exp_3919_auto
_database_code_depnum_ccdc_archive 'CCDC 2379595'
loop_
_audit_author_name
_audit_author_address
'Sunewang Rixin Wang'
;East China Normal University
China
;
_audit_update_record             
;
2024-08-24 deposited with the CCDC.	2025-10-06 downloaded from the CCDC.
;
_audit_creation_date             2024-01-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H26 O3'
_chemical_formula_sum            'C34 H26 O3'
_chemical_formula_weight         482.55
_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                   17.9007(2)
_cell_length_b                   10.25550(10)
_cell_length_c                   27.1733(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4988.49(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    18320
_cell_measurement_temperature    172(1)
_cell_measurement_theta_max      73.3950
_cell_measurement_theta_min      4.0620
_shelx_estimated_absorpt_T_max   0.872
_shelx_estimated_absorpt_T_min   0.803
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023)
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    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            57491
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.049
_diffrn_reflns_theta_max         67.049
_diffrn_reflns_theta_min         3.253
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  27.00   1.00    2.00    --    0.00 -37.00-150.00   55
  2  ω    -85.00 -26.00   1.00    2.00    --    0.00 -77.00-150.00   59
  3  ω     -9.00  33.00   1.00    2.00    --    0.00 -77.00-150.00   42
  4  ω    -27.00  12.00   1.00    2.00    --    0.00  37.00 120.00   39
  5  ω     43.00  69.00   1.00    2.00    --    0.00  57.00  30.00   26
  6  ω     40.00  66.00   1.00    2.00    --    0.00  37.00 120.00   26
  7  ω    -89.00  18.00   1.00    2.00    --    0.00 -57.00 120.00  107
  8  ω     69.00 164.00   1.00    3.00    --   92.10  45.00 -30.00   95
  9  ω     93.00 119.00   1.00    3.00    --   92.10 -82.00  30.00   26
 10  ω     11.00  53.00   1.00    3.00    --   92.10 -82.00-120.00   42
 11  ω     14.00  58.00   1.00    3.00    --   92.10 -82.00   0.00   44
 12  ω     66.00 182.00   1.00    3.00    --   92.10  45.00 -60.00  116
 13  ω     64.00 180.00   1.00    3.00    --   92.10  61.00  30.00  116
 14  ω      3.00 120.00   1.00    3.00    --   92.10 -61.00-150.00  117
 15  ω     11.00 128.00   1.00    3.00    --   92.10 -82.00  90.00  117
 16  ω      4.00  29.00   1.00    3.00    --   92.10 -82.00  30.00   25
 17  ω     69.00 109.00   1.00    3.00    --   92.10  30.00-180.00   40
 18  ω     76.00 128.00   1.00    3.00    --   92.10 -82.00 -60.00   52
 19  ω    130.00 156.00   1.00    3.00    --   92.10  30.00-180.00   26
 20  ω      7.00  33.00   1.00    3.00    --   92.10 -82.00 -60.00   26
 21  ω      4.00  46.00   1.00    3.00    --   92.10 -82.00-150.00   42
 22  ω     94.00 120.00   1.00    3.00    --   92.10 -82.00 120.00   26
 23  ω     71.00 128.00   1.00    3.00    --   92.10 -82.00-120.00   57
 24  ω     84.00 109.00   1.00    3.00    --   92.10 -82.00   0.00   25
 25  ω      6.00 119.00   1.00    3.00    --   92.10 -61.00  90.00  113
 26  ω     93.00 119.00   1.00    3.00    --   92.10 -82.00 -90.00   26
 27  ω     96.00 122.00   1.00    3.00    --   92.10 -82.00 150.00   26
 28  ω     61.00 122.00   1.00    3.00    --   92.10  82.00  30.00   61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0004771000
_diffrn_orient_matrix_UB_12      -0.0245096000
_diffrn_orient_matrix_UB_13      0.0559208000
_diffrn_orient_matrix_UB_21      -0.0122436000
_diffrn_orient_matrix_UB_22      -0.1466913000
_diffrn_orient_matrix_UB_23      -0.0090899000
_diffrn_orient_matrix_UB_31      0.0852291000
_diffrn_orient_matrix_UB_32      -0.0208607000
_diffrn_orient_matrix_UB_33      -0.0016603000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed 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                3952
_reflns_number_total             4455
_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 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00094(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4455
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.036
_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)+(0.0440P)²+1.6588P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1022
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C29(H29)
2.b Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C35(H35), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22),
  C23(H23), C25(H25), C26(H26), C27(H27), C28(H28), C34(H34)
;
_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 0.47894(5) 0.45136(9) 0.58355(3) 0.0301(2) Uani 1 1 d . . . . .
O2 O 0.57642(6) 0.77381(10) 0.55158(4) 0.0424(3) Uani 1 1 d . . . . .
O3 O 0.63708(7) 0.76315(13) 0.47971(4) 0.0565(3) Uani 1 1 d . . . . .
C1 C 0.59061(8) 0.37565(14) 0.54181(5) 0.0322(3) Uani 1 1 d . . . . .
C2 C 0.58470(9) 0.25277(14) 0.56286(6) 0.0409(4) Uani 1 1 d . . . . .
H2 H 0.551194 0.238558 0.589438 0.049 Uiso 1 1 calc R U . . .
C35 C 0.62781(10) 0.15069(17) 0.54502(7) 0.0543(5) Uani 1 1 d . . . . .
H35 H 0.623483 0.066528 0.559341 0.065 Uiso 1 1 calc R U . . .
C4 C 0.67706(10) 0.1707(2) 0.50649(7) 0.0595(5) Uani 1 1 d . . . . .
H4 H 0.707217 0.101026 0.494864 0.071 Uiso 1 1 calc R U . . .
C5 C 0.68217(10) 0.2918(2) 0.48512(7) 0.0559(5) Uani 1 1 d . . . . .
H5 H 0.715632 0.305476 0.458480 0.067 Uiso 1 1 calc R U . . .
C6 C 0.63895(9) 0.39342(17) 0.50217(5) 0.0429(4) Uani 1 1 d . . . . .
H6 H 0.642141 0.476370 0.486757 0.051 Uiso 1 1 calc R U . . .
C7 C 0.64074(7) 0.49931(12) 0.63368(4) 0.0270(3) Uani 1 1 d . . . . .
C8 C 0.61150(8) 0.40758(14) 0.66625(5) 0.0353(3) Uani 1 1 d . . . . .
H8 H 0.558896 0.396874 0.668495 0.042 Uiso 1 1 calc R U . . .
C9 C 0.65768(9) 0.33192(16) 0.69533(6) 0.0436(4) Uani 1 1 d . . . . .
H9 H 0.636730 0.268755 0.716855 0.052 Uiso 1 1 calc R U . . .
C10 C 0.73444(9) 0.34797(17) 0.69316(6) 0.0458(4) Uani 1 1 d . . . . .
H10 H 0.766287 0.296473 0.713269 0.055 Uiso 1 1 calc R U . . .
C11 C 0.76411(8) 0.43906(17) 0.66164(6) 0.0436(4) Uani 1 1 d . . . . .
H11 H 0.816687 0.451056 0.660230 0.052 Uiso 1 1 calc R U . . .
C12 C 0.71789(8) 0.51366(14) 0.63186(5) 0.0350(3) Uani 1 1 d . . . . .
H12 H 0.739269 0.575380 0.609918 0.042 Uiso 1 1 calc R U . . .
C13 C 0.38545(7) 0.53246(12) 0.63838(5) 0.0269(3) Uani 1 1 d . . . . .
C14 C 0.35893(8) 0.61125(14) 0.67636(5) 0.0325(3) Uani 1 1 d . . . . .
H14 H 0.389268 0.679774 0.688771 0.039 Uiso 1 1 calc R U . . .
C15 C 0.28868(8) 0.59025(15) 0.69609(5) 0.0397(3) Uani 1 1 d . . . . .
H15 H 0.271324 0.644522 0.722013 0.048 Uiso 1 1 calc R U . . .
C16 C 0.24347(9) 0.49143(16) 0.67859(6) 0.0418(4) Uani 1 1 d . . . . .
H16 H 0.195703 0.476642 0.692767 0.050 Uiso 1 1 calc R U . . .
C17 C 0.26842(8) 0.41428(15) 0.64026(6) 0.0401(3) Uani 1 1 d . . . . .
H17 H 0.237333 0.347024 0.627674 0.048 Uiso 1 1 calc R U . . .
C18 C 0.33860(8) 0.43459(13) 0.62010(5) 0.0323(3) Uani 1 1 d . . . . .
H18 H 0.355056 0.381492 0.593581 0.039 Uiso 1 1 calc R U . . .
C19 C 0.48931(7) 0.85773(12) 0.65180(5) 0.0283(3) Uani 1 1 d . . . . .
C20 C 0.52403(7) 0.73595(12) 0.66374(4) 0.0267(3) Uani 1 1 d . . . . .
C21 C 0.56688(7) 0.72740(14) 0.70588(5) 0.0312(3) Uani 1 1 d . . . . .
H21 H 0.590353 0.647047 0.713854 0.037 Uiso 1 1 calc R U . . .
C22 C 0.57652(8) 0.83561(15) 0.73735(5) 0.0370(3) Uani 1 1 d . . . . .
H22 H 0.605444 0.826925 0.766480 0.044 Uiso 1 1 calc R U . . .
C23 C 0.54459(9) 0.95221(15) 0.72617(5) 0.0381(3) Uani 1 1 d . . . . .
H23 H 0.551711 1.024600 0.747476 0.046 Uiso 1 1 calc R U . . .
C24 C 0.50102(8) 0.96683(13) 0.68329(5) 0.0338(3) Uani 1 1 d . . . . .
C25 C 0.46850(10) 1.08844(14) 0.67053(6) 0.0435(4) Uani 1 1 d . . . . .
H25 H 0.477090 1.162181 0.690921 0.052 Uiso 1 1 calc R U . . .
C26 C 0.42540(10) 1.10137(15) 0.62978(6) 0.0461(4) Uani 1 1 d . . . . .
H26 H 0.404296 1.183675 0.621772 0.055 Uiso 1 1 calc R U . . .
C27 C 0.41197(9) 0.99320(14) 0.59944(5) 0.0387(3) Uani 1 1 d . . . . .
H27 H 0.380786 1.002457 0.571369 0.046 Uiso 1 1 calc R U . . .
C28 C 0.44311(8) 0.87486(13) 0.60974(5) 0.0314(3) Uani 1 1 d . . . . .
H28 H 0.433804 0.803016 0.588538 0.038 Uiso 1 1 calc R U . . .
C29 C 0.54836(7) 0.49150(13) 0.56101(5) 0.0284(3) Uani 1 1 d . . . . .
H29 H 0.535927 0.548699 0.532355 0.034 Uiso 1 1 calc R U . . .
C30 C 0.58790(7) 0.57756(12) 0.60058(4) 0.0265(3) Uani 1 1 d . . . . .
C31 C 0.51903(7) 0.62356(12) 0.62945(4) 0.0250(3) Uani 1 1 d . . . . .
C32 C 0.46156(7) 0.54529(12) 0.61842(4) 0.0261(3) Uani 1 1 d . . . . .
C33 C 0.62978(8) 0.69051(14) 0.57626(5) 0.0325(3) Uani 1 1 d . . . . .
H33A H 0.657272 0.740990 0.601488 0.039 Uiso 1 1 calc R U . . .
H33B H 0.666362 0.656216 0.552201 0.039 Uiso 1 1 calc R U . . .
C34 C 0.58728(9) 0.80222(14) 0.50467(5) 0.0368(3) Uani 1 1 d . . . . .
H34 H 0.552167 0.858928 0.489534 0.044 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C29 1.4452(16) . ?
O1 C32 1.3867(15) . ?
O2 C33 1.4464(16) . ?
O2 C34 1.3220(17) . ?
O3 C34 1.1897(18) . ?
C1 C2 1.388(2) . ?
C1 C6 1.394(2) . ?
C1 C29 1.5020(18) . ?
C2 H2 0.9500 . ?
C2 C35 1.388(2) . ?
C35 H35 0.9500 . ?
C35 C4 1.384(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.373(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.379(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.3936(19) . ?
C7 C12 1.390(2) . ?
C7 C30 1.5322(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.382(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.374(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3941(18) . ?
C13 C18 1.3990(19) . ?
C13 C32 1.4723(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.4323(18) . ?
C19 C24 1.4242(18) . ?
C19 C28 1.4216(19) . ?
C20 C21 1.3811(18) . ?
C20 C31 1.4847(17) . ?
C21 H21 0.9500 . ?
C21 C22 1.412(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.360(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.410(2) . ?
C24 C25 1.419(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.356(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.403(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.3646(19) . ?
C28 H28 0.9500 . ?
C29 H29 1.0000 . ?
C29 C30 1.5608(17) . ?
C30 C31 1.5356(17) . ?
C30 C33 1.5299(18) . ?
C31 C32 1.3388(18) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34 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
C32 O1 C29 106.54(10) . . ?
C34 O2 C33 118.69(11) . . ?
C2 C1 C6 118.99(14) . . ?
C2 C1 C29 122.46(13) . . ?
C6 C1 C29 118.53(13) . . ?
C1 C2 H2 120.1 . . ?
C35 C2 C1 119.90(16) . . ?
C35 C2 H2 120.1 . . ?
C2 C35 H35 119.8 . . ?
C4 C35 C2 120.42(17) . . ?
C4 C35 H35 119.8 . . ?
C35 C4 H4 120.1 . . ?
C5 C4 C35 119.78(16) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.26(17) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.63(17) . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C30 119.63(12) . . ?
C12 C7 C8 117.86(12) . . ?
C12 C7 C30 122.49(12) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.16(14) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.15(14) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.38(14) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.53(14) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 H12 119.6 . . ?
C11 C12 C7 120.89(13) . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C18 118.34(12) . . ?
C14 C13 C32 122.41(12) . . ?
C18 C13 C32 119.21(12) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.40(13) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.88(14) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.34(14) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.31(14) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.70(13) . . ?
C17 C18 H18 119.6 . . ?
C24 C19 C20 119.02(12) . . ?
C28 C19 C20 122.84(12) . . ?
C28 C19 C24 118.14(12) . . ?
C19 C20 C31 120.57(11) . . ?
C21 C20 C19 118.96(12) . . ?
C21 C20 C31 120.30(12) . . ?
C20 C21 H21 119.3 . . ?
C20 C21 C22 121.35(13) . . ?
C22 C21 H21 119.3 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.31(13) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 119.6 . . ?
C22 C23 C24 120.71(13) . . ?
C24 C23 H23 119.6 . . ?
C23 C24 C19 119.63(13) . . ?
C23 C24 C25 121.48(13) . . ?
C25 C24 C19 118.90(13) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 C24 121.24(14) . . ?
C26 C25 H25 119.4 . . ?
C25 C26 H26 120.0 . . ?
C25 C26 C27 120.00(14) . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 119.6 . . ?
C28 C27 C26 120.85(15) . . ?
C28 C27 H27 119.6 . . ?
C19 C28 H28 119.6 . . ?
C27 C28 C19 120.82(13) . . ?
C27 C28 H28 119.6 . . ?
O1 C29 C1 110.79(11) . . ?
O1 C29 H29 107.8 . . ?
O1 C29 C30 105.01(10) . . ?
C1 C29 H29 107.8 . . ?
C1 C29 C30 117.27(11) . . ?
C30 C29 H29 107.8 . . ?
C7 C30 C29 112.84(10) . . ?
C7 C30 C31 110.90(10) . . ?
C31 C30 C29 99.30(10) . . ?
C33 C30 C7 110.34(11) . . ?
C33 C30 C29 110.66(10) . . ?
C33 C30 C31 112.43(10) . . ?
C20 C31 C30 120.71(11) . . ?
C32 C31 C20 130.72(12) . . ?
C32 C31 C30 108.56(11) . . ?
O1 C32 C13 113.41(11) . . ?
C31 C32 O1 113.40(11) . . ?
C31 C32 C13 133.01(12) . . ?
O2 C33 C30 108.90(11) . . ?
O2 C33 H33A 109.9 . . ?
O2 C33 H33B 109.9 . . ?
C30 C33 H33A 109.9 . . ?
C30 C33 H33B 109.9 . . ?
H33A C33 H33B 108.3 . . ?
O2 C34 H34 117.1 . . ?
O3 C34 O2 125.86(14) . . ?
O3 C34 H34 117.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C29 C30 C7 92.09(12) . . . . ?
O1 C29 C30 C31 -25.38(12) . . . . ?
O1 C29 C30 C33 -143.73(10) . . . . ?
C1 C2 C35 C4 0.4(2) . . . . ?
C1 C29 C30 C7 -31.39(16) . . . . ?
C1 C29 C30 C31 -148.86(11) . . . . ?
C1 C29 C30 C33 92.79(14) . . . . ?
C2 C1 C6 C5 -2.2(2) . . . . ?
C2 C1 C29 O1 -29.10(17) . . . . ?
C2 C1 C29 C30 91.39(16) . . . . ?
C2 C35 C4 C5 -1.3(2) . . . . ?
C35 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 1.2(2) . . . . ?
C6 C1 C2 C35 1.4(2) . . . . ?
C6 C1 C29 O1 152.58(12) . . . . ?
C6 C1 C29 C30 -86.93(15) . . . . ?
C7 C8 C9 C10 1.2(2) . . . . ?
C7 C30 C31 C20 76.97(14) . . . . ?
C7 C30 C31 C32 -101.61(12) . . . . ?
C7 C30 C33 O2 -171.20(10) . . . . ?
C8 C7 C12 C11 -0.1(2) . . . . ?
C8 C7 C30 C29 -67.51(15) . . . . ?
C8 C7 C30 C31 42.89(16) . . . . ?
C8 C7 C30 C33 168.14(12) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C10 C11 C12 C7 0.9(2) . . . . ?
C12 C7 C8 C9 -0.9(2) . . . . ?
C12 C7 C30 C29 110.91(14) . . . . ?
C12 C7 C30 C31 -138.69(13) . . . . ?
C12 C7 C30 C33 -13.45(17) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C14 C13 C18 C17 -1.81(19) . . . . ?
C14 C13 C32 O1 175.25(11) . . . . ?
C14 C13 C32 C31 0.6(2) . . . . ?
C14 C15 C16 C17 -1.2(2) . . . . ?
C15 C16 C17 C18 1.0(2) . . . . ?
C16 C17 C18 C13 0.5(2) . . . . ?
C18 C13 C14 C15 1.63(19) . . . . ?
C18 C13 C32 O1 -2.21(16) . . . . ?
C18 C13 C32 C31 -176.88(13) . . . . ?
C19 C20 C21 C22 0.47(19) . . . . ?
C19 C20 C31 C30 108.99(14) . . . . ?
C19 C20 C31 C32 -72.78(18) . . . . ?
C19 C24 C25 C26 1.6(2) . . . . ?
C20 C19 C24 C23 -1.79(19) . . . . ?
C20 C19 C24 C25 178.00(12) . . . . ?
C20 C19 C28 C27 -179.11(13) . . . . ?
C20 C21 C22 C23 -1.2(2) . . . . ?
C20 C31 C32 O1 179.01(12) . . . . ?
C20 C31 C32 C13 -6.3(2) . . . . ?
C21 C20 C31 C30 -66.22(16) . . . . ?
C21 C20 C31 C32 112.01(16) . . . . ?
C21 C22 C23 C24 0.5(2) . . . . ?
C22 C23 C24 C19 1.1(2) . . . . ?
C22 C23 C24 C25 -178.73(14) . . . . ?
C23 C24 C25 C26 -178.65(15) . . . . ?
C24 C19 C20 C21 1.03(19) . . . . ?
C24 C19 C20 C31 -174.24(11) . . . . ?
C24 C19 C28 C27 1.1(2) . . . . ?
C24 C25 C26 C27 0.3(2) . . . . ?
C25 C26 C27 C28 -1.4(2) . . . . ?
C26 C27 C28 C19 0.7(2) . . . . ?
C28 C19 C20 C21 -178.74(12) . . . . ?
C28 C19 C20 C31 5.98(19) . . . . ?
C28 C19 C24 C23 177.99(12) . . . . ?
C28 C19 C24 C25 -2.21(19) . . . . ?
C29 O1 C32 C13 169.19(10) . . . . ?
C29 O1 C32 C31 -15.05(14) . . . . ?
C29 C1 C2 C35 -176.93(13) . . . . ?
C29 C1 C6 C5 176.20(14) . . . . ?
C29 C30 C31 C20 -164.11(11) . . . . ?
C29 C30 C31 C32 17.31(13) . . . . ?
C29 C30 C33 O2 63.20(14) . . . . ?
C30 C7 C8 C9 177.60(13) . . . . ?
C30 C7 C12 C11 -178.58(13) . . . . ?
C30 C31 C32 O1 -2.60(14) . . . . ?
C30 C31 C32 C13 172.07(13) . . . . ?
C31 C20 C21 C22 175.75(12) . . . . ?
C31 C30 C33 O2 -46.83(14) . . . . ?
C32 O1 C29 C1 153.04(10) . . . . ?
C32 O1 C29 C30 25.51(12) . . . . ?
C32 C13 C14 C15 -175.86(13) . . . . ?
C32 C13 C18 C17 175.75(12) . . . . ?
C33 O2 C34 O3 1.6(2) . . . . ?
C33 C30 C31 C20 -47.09(15) . . . . ?
C33 C30 C31 C32 134.33(11) . . . . ?
C34 O2 C33 C30 -127.05(13) . . . . ?

_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 3.582
_oxdiff_exptl_absorpt_empirical_full_min 0.455
####################################################################### 
# 
# 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_exp_4516_auto
_database_code_depnum_ccdc_archive 'CCDC 2395142'
loop_
_audit_author_name
_audit_author_address
'Sunewang Rixin Wang'
;East China Normal University
China
;
_audit_update_record             
;
2024-10-31 deposited with the CCDC.	2025-10-06 downloaded from the CCDC.
;
_audit_creation_date             2024-10-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C35 H22 Br Cl O2'
_chemical_formula_sum            'C35 H22 Br Cl O2'
_chemical_formula_weight         589.88
_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'
Cl Cl 0.3639 0.7018 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   5.9069(2)
_cell_length_b                   28.0225(8)
_cell_length_c                   15.8563(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.222(3)
_cell_angle_gamma                90
_cell_volume                     2620.48(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16787
_cell_measurement_temperature    172.95(11)
_cell_measurement_theta_max      73.0410
_cell_measurement_theta_min      3.1950
_shelx_estimated_absorpt_T_max   0.691
_shelx_estimated_absorpt_T_min   0.515
_exptl_absorpt_coefficient_mu    3.329
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023)
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    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1383
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            66414
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         3.154
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.95(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00 -37.00   1.00    2.00    --    0.00 -76.00 -51.00   26
  2  ω    -11.00  33.00   1.00    2.00    --    0.00 -76.00 -51.00   44
  3  ω      3.00 107.00   1.00    2.00    --   92.10 -76.00 -51.00  104
  4  ω     59.00 113.00   1.00    2.00    --   92.10  76.00  75.00   54
  5  ω    -25.00  15.00   1.00    2.00    --    0.00  37.00-120.00   40
  6  ω    -26.00  88.00   1.00    2.00    --    0.00  37.00  60.00  114
  7  ω    -29.00  -3.00   1.00    2.00    --    0.00  76.00  75.00   26
  8  ω    -26.00   4.00   1.00    2.00    --    0.00  57.00  90.00   30
  9  ω    -12.00  72.00   1.00    2.00    --    0.00  82.00 -90.00   84
 10  ω     19.00  89.00   1.00    2.00    --    0.00  37.00-120.00   70
 11  ω     10.00  60.00   1.00    2.00    --    0.00  57.00  90.00   50
 12  ω    -29.00  74.00   1.00    2.00    --    0.00  77.00 -30.00  103
 13  ω      3.00 125.00   1.00    2.00    --   92.10 -77.00-180.00  122
 14  ω     57.00  82.00   1.00    2.00    --   92.10  82.00 150.00   25
 15  ω     96.00 122.00   1.00    2.00    --   92.10  60.00 141.35   26
 16  ω     59.00  86.00   1.00    2.00    --   92.10  77.00  60.00   27
 17  ω     59.00 114.00   1.00    2.00    --   92.10  77.00-120.00   55
 18  ω    136.00 182.00   1.00    2.00    --   92.10  77.00-120.00   46
 19  ω     57.00  83.00   1.00    2.00    --   92.10  82.00-180.00   26
 20  ω      9.00 128.00   1.00    2.00    --   92.10 -82.00  30.00  119
 21  ω    139.00 182.00   1.00    2.00    --   92.10  82.00 130.04   43
 22  ω    144.00 182.00   1.00    2.00    --   92.10  61.00 -45.71   38
 23  ω     64.00  90.00   1.00    2.00    --   92.10  60.00 141.35   26
 24  ω     59.00  84.00   1.00    2.00    --   92.10  77.00 -30.00   25
 25  ω     59.00  85.00   1.00    2.00    --   92.10  77.00 -60.00   26
 26  ω    138.00 163.00   1.00    2.00    --   92.10  77.00 -60.00   25
 27  ω     59.00  97.00   1.00    2.00    --   92.10  77.00  90.00   38
 28  ω    103.00 129.00   1.00    2.00    --   92.10  77.00  90.00   26
 29  ω    144.00 170.00   1.00    2.00    --   92.10  77.00  90.00   26
 30  ω     57.00  83.00   1.00    2.00    --   92.10  82.00 -90.00   26
 31  ω    154.00 180.00   1.00    2.00    --   92.10  82.00 -90.00   26
 32  ω     63.00  89.00   1.00    2.00    --   92.10  66.00 -81.49   26
 33  ω     66.00 181.00   1.00    2.00    --   92.10  45.00  90.00  115
 34  ω     59.00  84.00   1.00    2.00    --   92.10  77.00 120.00   25
 35  ω     57.00  83.00   1.00    2.00    --   92.10  82.00 130.04   26
 36  ω     36.00 126.00   1.00    2.00    --   92.10 -82.00  90.00   90
 37  ω    157.00 182.00   1.00    2.00    --   92.10  60.00  45.96   25
 38  ω     64.00  98.00   1.00    2.00    --   92.10  61.00 -45.71   34
 39  ω      9.00  35.00   1.00    2.00    --   92.10 -82.00  90.00   26
 40  ω     57.00  82.00   1.00    2.00    --   92.10  82.00-120.00   25
 41  ω     57.00  82.00   1.00    2.00    --   92.10  82.00  90.00   25
 42  ω     61.00  87.00   1.00    2.00    --   92.10  73.00 -87.40   26
 43  ω     57.00  83.00   1.00    2.00    --   92.10  82.00 -60.00   26
 44  ω     67.00 118.00   1.00    2.00    --   92.10  51.00  26.63   51
 45  ω     57.00  86.00   1.00    2.00    --   92.10  82.00-150.00   29
 46  ω     64.00 117.00   1.00    2.00    --   92.10  60.00  45.96   53
 47  ω     65.00 182.00   1.00    2.00    --   92.10  57.00 171.16  117
 48  ω     57.00  83.00   1.00    2.00    --   92.10  82.00 -30.00   26
 49  ω     57.00  82.00   1.00    2.00    --   92.10  82.00  30.00   25
 50  ω     57.00  82.00   1.00    2.00    --   92.10  82.00 120.00   25
 51  ω     64.00  89.00   1.00    2.00    --   92.10  62.00-156.38   25
 52  ω    128.00 153.00   1.00    2.00    --   92.10  62.00-156.38   25
 53  ω     59.00  84.00   1.00    2.00    --   92.10  77.00  -4.76   25
 54  ω    108.00 148.00   1.00    2.00    --   92.10  77.00  -4.76   40
 55  ω     66.00 120.00   1.00    2.00    --   92.10  46.00-144.05   54
 56  ω     66.00 182.00   1.00    2.00    --   92.10  45.00-105.50  116
 57  ω     59.00  84.00   1.00    2.00    --   92.10  78.00  15.07   25
 58  ω     58.00  83.00   1.00    2.00    --   92.10  79.00-157.11   25
 59  ω     66.00 164.00   1.00    2.00    --   92.10  45.00 150.00   98
 60  ω     67.00 160.00   1.00    2.00    --   92.10  45.00 -53.91   93
 61  ω    130.00 179.00   1.00    2.00    --   92.10  77.00  30.00   49
 62  ω    117.00 179.00   1.00    2.00    --   92.10  66.00 -81.49   62
 63  ω     59.00  84.00   1.00    2.00    --   92.10  77.00  30.00   25
 64  ω     12.00 125.00   1.00    2.00    --   92.10 -82.00-120.00  113
 65  ω    129.00 182.00   1.00    2.00    --   92.10  82.00-180.00   53
 66  ω     75.00 103.00   1.00    2.00    --   92.10 -82.00 150.00   28
 67  ω     63.00 174.00   1.00    2.00    --   92.10  64.00 -22.42  111
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0057171000
_diffrn_orient_matrix_UB_12      -0.0446304000
_diffrn_orient_matrix_UB_13      0.0565021000
_diffrn_orient_matrix_UB_21      0.2513738000
_diffrn_orient_matrix_UB_22      -0.0096308000
_diffrn_orient_matrix_UB_23      -0.0150709000
_diffrn_orient_matrix_UB_31      0.0711421000
_diffrn_orient_matrix_UB_32      0.0306109000
_diffrn_orient_matrix_UB_33      0.0777557000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed 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                4101
_reflns_number_total             4666
_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 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.751
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4666
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0742
_refine_ls_restrained_S_all      1.134
_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)+(0.0633P)²+18.1784P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2020
_refine_ls_wR_factor_ref         0.2055
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C3(H3), C2(H2), C26(H26), C25(H25), C20(H20), C14(H14), C5(H5),
 C17(H17), C22(H22), C15(H15), C19(H19), C6(H6), C28(H28), C31(H31), C12(H12),
 C16(H16), C34(H34), C33(H33)
2.b Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C)
;
_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 0.76346(14) 0.43239(3) -0.20911(4) 0.0464(3) Uani 1 1 d . . . . .
Cl1 Cl 1.0185(3) 0.55096(5) 0.40081(10) 0.0369(4) Uani 1 1 d . . . . .
O1 O 0.1385(7) 0.32962(13) 0.3112(2) 0.0262(9) Uani 1 1 d . . . . .
O2 O 0.5347(7) 0.39242(14) 0.1006(2) 0.0293(9) Uani 1 1 d . . . . .
C23 C 0.6268(10) 0.5029(2) 0.4035(3) 0.0279(12) Uani 1 1 d . . . . .
H23 H 0.580941 0.527493 0.440146 0.033 Uiso 1 1 calc R U . . .
C7 C 0.2814(10) 0.35952(19) 0.3585(3) 0.0235(11) Uani 1 1 d . . . . .
C3 C 0.0962(11) 0.3241(2) 0.5729(4) 0.0296(13) Uani 1 1 d . . . . .
H3 H -0.030520 0.309263 0.596406 0.036 Uiso 1 1 calc R U . . .
C21 C 0.5474(10) 0.42896(18) 0.3286(3) 0.0240(11) Uani 1 1 d . . . . .
C2 C 0.0966(10) 0.33117(19) 0.4865(4) 0.0267(12) Uani 1 1 d . . . . .
H2 H -0.030589 0.321471 0.451346 0.032 Uiso 1 1 calc R U . . .
C26 C 0.7570(10) 0.4324(2) 0.2931(4) 0.0283(12) Uani 1 1 d . . . . .
H26 H 0.800943 0.408750 0.254452 0.034 Uiso 1 1 calc R U . . .
C10 C 0.1566(10) 0.34150(19) 0.2278(3) 0.0241(11) Uani 1 1 d . . . . .
C35 C 0.2734(13) 0.3323(3) 0.7206(4) 0.0438(17) Uani 1 1 d . . . . .
H35A H 0.182004 0.357824 0.743750 0.066 Uiso 1 1 calc R U . . .
H35B H 0.428029 0.333776 0.746297 0.066 Uiso 1 1 calc R U . . .
H35C H 0.206047 0.301299 0.732970 0.066 Uiso 1 1 calc R U . . .
C8 C 0.3922(10) 0.38942(19) 0.3062(3) 0.0246(12) Uani 1 1 d . . . . .
C25 C 0.9027(10) 0.4700(2) 0.3135(4) 0.0292(13) Uani 1 1 d . . . . .
H25 H 1.045935 0.472121 0.289337 0.035 Uiso 1 1 calc R U . . .
C1 C 0.2827(10) 0.35251(18) 0.4504(3) 0.0221(11) Uani 1 1 d . . . . .
C20 C -0.2000(10) 0.2960(2) 0.1894(3) 0.0263(12) Uani 1 1 d . . . . .
H20 H -0.236946 0.296378 0.246947 0.032 Uiso 1 1 calc R U . . .
C13 C -0.0944(10) 0.29636(19) 0.0196(3) 0.0249(12) Uani 1 1 d . . . . .
C24 C 0.8360(10) 0.50454(19) 0.3698(3) 0.0266(12) Uani 1 1 d . . . . .
C14 C -0.0483(11) 0.2981(2) -0.0677(4) 0.0312(13) Uani 1 1 d . . . . .
H14 H 0.090355 0.311238 -0.084465 0.037 Uiso 1 1 calc R U . . .
C32 C 0.5837(11) 0.4361(2) -0.1141(4) 0.0332(14) Uani 1 1 d . . . . .
C5 C 0.4637(11) 0.3595(2) 0.5895(4) 0.0289(12) Uani 1 1 d . . . . .
H5 H 0.590092 0.369551 0.624839 0.035 Uiso 1 1 calc R U . . .
C27 C 0.3413(10) 0.40349(19) 0.1434(3) 0.0254(12) Uani 1 1 d . . . . .
C17 C -0.4539(11) 0.2578(2) -0.0191(4) 0.0303(13) Uani 1 1 d . . . . .
H17 H -0.591462 0.243676 -0.003505 0.036 Uiso 1 1 calc R U . . .
C9 C 0.3079(10) 0.37770(19) 0.2219(3) 0.0241(11) Uani 1 1 d . . . . .
C22 C 0.4836(10) 0.4649(2) 0.3833(3) 0.0262(12) Uani 1 1 d . . . . .
H22 H 0.339753 0.463373 0.407099 0.031 Uiso 1 1 calc R U . . .
C18 C -0.2992(10) 0.27619(19) 0.0437(4) 0.0278(12) Uani 1 1 d . . . . .
C15 C -0.2029(12) 0.2808(2) -0.1269(4) 0.0364(15) Uani 1 1 d . . . . .
H15 H -0.172830 0.282648 -0.185011 0.044 Uiso 1 1 calc R U . . .
C19 C -0.3459(10) 0.27588(19) 0.1305(4) 0.0286(13) Uani 1 1 d . . . . .
H19 H -0.481283 0.261373 0.147607 0.034 Uiso 1 1 calc R U . . .
C6 C 0.4669(10) 0.36624(19) 0.5033(4) 0.0268(12) Uani 1 1 d . . . . .
H6 H 0.595688 0.380314 0.480035 0.032 Uiso 1 1 calc R U . . .
C11 C 0.0093(10) 0.31670(19) 0.1657(3) 0.0252(12) Uani 1 1 d . . . . .
C4 C 0.2798(11) 0.3385(2) 0.6257(4) 0.0315(13) Uani 1 1 d . . . . .
C29 C 0.3083(11) 0.4408(2) 0.0192(4) 0.0315(13) Uani 1 1 d . . . . .
C28 C 0.2030(12) 0.4328(2) 0.0983(4) 0.0343(14) Uani 1 1 d . . . . .
H28 H 0.063699 0.445786 0.114756 0.041 Uiso 1 1 calc R U . . .
C31 C 0.6526(11) 0.4120(2) -0.0410(4) 0.0313(13) Uani 1 1 d . . . . .
H31 H 0.790556 0.394550 -0.035776 0.038 Uiso 1 1 calc R U . . .
C12 C 0.0585(10) 0.31557(19) 0.0817(3) 0.0248(12) Uani 1 1 d . . . . .
H12 H 0.199093 0.328077 0.065396 0.030 Uiso 1 1 calc R U . . .
C16 C -0.4065(11) 0.2604(2) -0.1028(4) 0.0357(14) Uani 1 1 d . . . . .
H16 H -0.512272 0.248183 -0.144742 0.043 Uiso 1 1 calc R U . . .
C34 C 0.2423(12) 0.4654(2) -0.0556(4) 0.0414(16) Uani 1 1 d . . . . .
H34 H 0.105661 0.483366 -0.060647 0.050 Uiso 1 1 calc R U . . .
C33 C 0.3872(12) 0.4623(2) -0.1220(4) 0.0408(16) Uani 1 1 d . . . . .
H33 H 0.349338 0.478609 -0.173468 0.049 Uiso 1 1 calc R U . . .
C30 C 0.5070(11) 0.4151(2) 0.0238(3) 0.0271(12) Uani 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
Br1 C32 1.894(6) . ?
Cl1 C24 1.742(6) . ?
O1 C7 1.380(7) . ?
O1 C10 1.374(6) . ?
O2 C27 1.397(7) . ?
O2 C30 1.374(6) . ?
C23 H23 0.9500 . ?
C23 C24 1.374(8) . ?
C23 C22 1.385(8) . ?
C7 C8 1.371(8) . ?
C7 C1 1.470(7) . ?
C3 H3 0.9500 . ?
C3 C2 1.384(8) . ?
C3 C4 1.392(9) . ?
C21 C26 1.392(8) . ?
C21 C8 1.468(8) . ?
C21 C22 1.396(7) . ?
C2 H2 0.9500 . ?
C2 C1 1.402(8) . ?
C26 H26 0.9500 . ?
C26 C25 1.387(8) . ?
C10 C9 1.359(8) . ?
C10 C11 1.454(8) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C35 C4 1.517(8) . ?
C8 C9 1.439(8) . ?
C25 H25 0.9500 . ?
C25 C24 1.388(8) . ?
C1 C6 1.390(8) . ?
C20 H20 0.9500 . ?
C20 C19 1.358(8) . ?
C20 C11 1.435(8) . ?
C13 C14 1.426(8) . ?
C13 C18 1.407(8) . ?
C13 C12 1.406(8) . ?
C14 H14 0.9500 . ?
C14 C15 1.361(9) . ?
C32 C31 1.382(9) . ?
C32 C33 1.374(10) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(8) . ?
C5 C4 1.388(9) . ?
C27 C9 1.462(7) . ?
C27 C28 1.337(9) . ?
C17 H17 0.9500 . ?
C17 C18 1.410(8) . ?
C17 C16 1.373(9) . ?
C22 H22 0.9500 . ?
C18 C19 1.419(8) . ?
C15 H15 0.9500 . ?
C15 C16 1.404(9) . ?
C19 H19 0.9500 . ?
C6 H6 0.9500 . ?
C11 C12 1.380(8) . ?
C29 C28 1.447(8) . ?
C29 C34 1.409(9) . ?
C29 C30 1.375(9) . ?
C28 H28 0.9500 . ?
C31 H31 0.9500 . ?
C31 C30 1.380(8) . ?
C12 H12 0.9500 . ?
C16 H16 0.9500 . ?
C34 H34 0.9500 . ?
C34 C33 1.397(9) . ?
C33 H33 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
C10 O1 C7 107.3(4) . . ?
C30 O2 C27 105.5(4) . . ?
C24 C23 H23 120.5 . . ?
C24 C23 C22 119.1(5) . . ?
C22 C23 H23 120.5 . . ?
O1 C7 C1 115.2(4) . . ?
C8 C7 O1 109.9(5) . . ?
C8 C7 C1 134.8(5) . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(5) . . ?
C4 C3 H3 119.7 . . ?
C26 C21 C8 120.9(5) . . ?
C26 C21 C22 118.5(5) . . ?
C22 C21 C8 120.6(5) . . ?
C3 C2 H2 119.6 . . ?
C3 C2 C1 120.7(6) . . ?
C1 C2 H2 119.6 . . ?
C21 C26 H26 119.5 . . ?
C25 C26 C21 120.9(5) . . ?
C25 C26 H26 119.5 . . ?
O1 C10 C11 117.4(5) . . ?
C9 C10 O1 109.5(5) . . ?
C9 C10 C11 132.9(5) . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C4 C35 H35A 109.5 . . ?
C4 C35 H35B 109.5 . . ?
C4 C35 H35C 109.5 . . ?
C7 C8 C21 128.9(5) . . ?
C7 C8 C9 105.7(5) . . ?
C9 C8 C21 125.1(5) . . ?
C26 C25 H25 120.5 . . ?
C26 C25 C24 118.9(5) . . ?
C24 C25 H25 120.5 . . ?
C2 C1 C7 120.1(5) . . ?
C6 C1 C7 121.4(5) . . ?
C6 C1 C2 118.4(5) . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C11 120.7(5) . . ?
C11 C20 H20 119.6 . . ?
C18 C13 C14 119.4(5) . . ?
C12 C13 C14 121.1(5) . . ?
C12 C13 C18 119.5(5) . . ?
C23 C24 Cl1 118.1(4) . . ?
C23 C24 C25 121.4(5) . . ?
C25 C24 Cl1 120.5(5) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0(6) . . ?
C15 C14 H14 120.0 . . ?
C31 C32 Br1 119.3(5) . . ?
C33 C32 Br1 117.7(5) . . ?
C33 C32 C31 123.0(6) . . ?
C6 C5 H5 119.3 . . ?
C6 C5 C4 121.4(6) . . ?
C4 C5 H5 119.3 . . ?
O2 C27 C9 117.2(5) . . ?
C28 C27 O2 111.6(5) . . ?
C28 C27 C9 130.7(6) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.3(6) . . ?
C10 C9 C8 107.5(5) . . ?
C10 C9 C27 123.3(5) . . ?
C8 C9 C27 128.5(5) . . ?
C23 C22 C21 121.1(5) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C13 C18 C17 119.1(5) . . ?
C13 C18 C19 118.9(5) . . ?
C17 C18 C19 122.0(5) . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.6(6) . . ?
C16 C15 H15 119.7 . . ?
C20 C19 C18 121.0(5) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.4(5) . . ?
C5 C6 H6 119.8 . . ?
C20 C11 C10 120.5(5) . . ?
C12 C11 C10 121.0(5) . . ?
C12 C11 C20 118.4(5) . . ?
C3 C4 C35 120.1(6) . . ?
C5 C4 C3 118.5(5) . . ?
C5 C4 C35 121.5(6) . . ?
C34 C29 C28 133.9(6) . . ?
C30 C29 C28 106.3(5) . . ?
C30 C29 C34 119.8(6) . . ?
C27 C28 C29 106.2(5) . . ?
C27 C28 H28 126.9 . . ?
C29 C28 H28 126.9 . . ?
C32 C31 H31 122.3 . . ?
C30 C31 C32 115.3(6) . . ?
C30 C31 H31 122.3 . . ?
C13 C12 H12 119.2 . . ?
C11 C12 C13 121.5(5) . . ?
C11 C12 H12 119.2 . . ?
C17 C16 C15 120.5(6) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C29 C34 H34 121.6 . . ?
C33 C34 C29 116.9(6) . . ?
C33 C34 H34 121.6 . . ?
C32 C33 C34 121.0(6) . . ?
C32 C33 H33 119.5 . . ?
C34 C33 H33 119.5 . . ?
O2 C30 C29 110.4(5) . . ?
O2 C30 C31 125.6(6) . . ?
C29 C30 C31 124.0(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
Br1 C32 C31 C30 -177.6(4) . . . . ?
Br1 C32 C33 C34 178.0(6) . . . . ?
O1 C7 C8 C21 175.4(5) . . . . ?
O1 C7 C8 C9 1.3(6) . . . . ?
O1 C7 C1 C2 -23.0(7) . . . . ?
O1 C7 C1 C6 156.4(5) . . . . ?
O1 C10 C9 C8 0.4(6) . . . . ?
O1 C10 C9 C27 -170.5(5) . . . . ?
O1 C10 C11 C20 24.0(8) . . . . ?
O1 C10 C11 C12 -160.9(5) . . . . ?
O2 C27 C9 C10 -103.7(7) . . . . ?
O2 C27 C9 C8 87.4(7) . . . . ?
O2 C27 C28 C29 1.6(7) . . . . ?
C7 O1 C10 C9 0.4(6) . . . . ?
C7 O1 C10 C11 -176.1(5) . . . . ?
C7 C8 C9 C10 -1.0(6) . . . . ?
C7 C8 C9 C27 169.3(6) . . . . ?
C7 C1 C6 C5 179.6(5) . . . . ?
C3 C2 C1 C7 179.6(5) . . . . ?
C3 C2 C1 C6 0.2(8) . . . . ?
C21 C26 C25 C24 -0.3(9) . . . . ?
C21 C8 C9 C10 -175.4(5) . . . . ?
C21 C8 C9 C27 -5.1(9) . . . . ?
C2 C3 C4 C35 177.6(6) . . . . ?
C2 C3 C4 C5 -0.8(9) . . . . ?
C2 C1 C6 C5 -1.0(8) . . . . ?
C26 C21 C8 C7 130.2(6) . . . . ?
C26 C21 C8 C9 -56.8(8) . . . . ?
C26 C21 C22 C23 -1.2(8) . . . . ?
C26 C25 C24 Cl1 177.2(5) . . . . ?
C26 C25 C24 C23 -2.0(9) . . . . ?
C10 O1 C7 C8 -1.1(6) . . . . ?
C10 O1 C7 C1 179.2(5) . . . . ?
C10 C11 C12 C13 -172.9(5) . . . . ?
C8 C7 C1 C2 157.4(6) . . . . ?
C8 C7 C1 C6 -23.2(10) . . . . ?
C8 C21 C26 C25 179.3(5) . . . . ?
C8 C21 C22 C23 -178.7(5) . . . . ?
C1 C7 C8 C21 -5.0(11) . . . . ?
C1 C7 C8 C9 -179.1(6) . . . . ?
C20 C11 C12 C13 2.3(8) . . . . ?
C13 C14 C15 C16 -1.3(10) . . . . ?
C13 C18 C19 C20 2.1(8) . . . . ?
C24 C23 C22 C21 -1.0(9) . . . . ?
C14 C13 C18 C17 0.4(8) . . . . ?
C14 C13 C18 C19 -178.3(5) . . . . ?
C14 C13 C12 C11 176.0(5) . . . . ?
C14 C15 C16 C17 0.6(10) . . . . ?
C32 C31 C30 O2 176.8(5) . . . . ?
C32 C31 C30 C29 -1.3(9) . . . . ?
C27 O2 C30 C29 1.9(6) . . . . ?
C27 O2 C30 C31 -176.4(6) . . . . ?
C17 C18 C19 C20 -176.5(5) . . . . ?
C9 C10 C11 C20 -151.4(6) . . . . ?
C9 C10 C11 C12 23.6(10) . . . . ?
C9 C27 C28 C29 -169.7(6) . . . . ?
C22 C23 C24 Cl1 -176.6(4) . . . . ?
C22 C23 C24 C25 2.6(9) . . . . ?
C22 C21 C26 C25 1.9(9) . . . . ?
C22 C21 C8 C7 -52.4(8) . . . . ?
C22 C21 C8 C9 120.6(6) . . . . ?
C18 C13 C14 C15 0.8(9) . . . . ?
C18 C13 C12 C11 -2.3(8) . . . . ?
C18 C17 C16 C15 0.6(9) . . . . ?
C19 C20 C11 C10 175.1(5) . . . . ?
C19 C20 C11 C12 -0.1(8) . . . . ?
C6 C5 C4 C3 0.0(9) . . . . ?
C6 C5 C4 C35 -178.4(6) . . . . ?
C11 C10 C9 C8 176.1(6) . . . . ?
C11 C10 C9 C27 5.2(10) . . . . ?
C11 C20 C19 C18 -2.2(9) . . . . ?
C4 C3 C2 C1 0.7(9) . . . . ?
C4 C5 C6 C1 0.9(9) . . . . ?
C29 C34 C33 C32 0.4(11) . . . . ?
C28 C27 C9 C10 67.1(9) . . . . ?
C28 C27 C9 C8 -101.8(8) . . . . ?
C28 C29 C34 C33 -175.7(7) . . . . ?
C28 C29 C30 O2 -1.0(7) . . . . ?
C28 C29 C30 C31 177.4(6) . . . . ?
C31 C32 C33 C34 -1.1(11) . . . . ?
C12 C13 C14 C15 -177.5(6) . . . . ?
C12 C13 C18 C17 178.7(5) . . . . ?
C12 C13 C18 C19 0.1(8) . . . . ?
C16 C17 C18 C13 -1.0(8) . . . . ?
C16 C17 C18 C19 177.6(6) . . . . ?
C34 C29 C28 C27 175.6(7) . . . . ?
C34 C29 C30 O2 -177.6(6) . . . . ?
C34 C29 C30 C31 0.7(10) . . . . ?
C33 C32 C31 C30 1.5(9) . . . . ?
C30 O2 C27 C9 170.3(5) . . . . ?
C30 O2 C27 C28 -2.2(6) . . . . ?
C30 C29 C28 C27 -0.4(7) . . . . ?
C30 C29 C34 C33 -0.2(10) . . . . ?

_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 4.952
_oxdiff_exptl_absorpt_empirical_full_min 0.383
