# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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 
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data_190418_ylf0417_0m
_database_code_depnum_ccdc_archive 'CCDC 1938578'
loop_
_audit_author_name
_audit_author_address
'Fulin Yang'
;Zhejiang University
China
;
_audit_update_record             
;
2019-07-05 deposited with the CCDC.	2021-12-14 downloaded from the CCDC.
;
_audit_creation_date             2019-04-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C35 H23 Cl O2'
_chemical_formula_sum            'C35 H23 Cl O2'
_chemical_formula_weight         510.98
_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 0.0033 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'
Cl Cl 0.1484 0.1585 '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      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                   12.0595(3)
_cell_length_b                   11.2560(3)
_cell_length_c                   20.0268(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.7890(10)
_cell_angle_gamma                90
_cell_volume                     2678.89(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8672
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.934
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0742 before and 0.0407 after correction.
The Ratio of minimum to maximum transmission is 0.9262.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.361
_exptl_crystal_size_min          0.31
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15763
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.374
_diffrn_reflns_theta_min         2.448
_diffrn_ambient_temperature      170.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4448
_reflns_number_total             5416
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.374
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5416
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.029
_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)+(0.0680P)²+1.4354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1463
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23),
  C25(H25), C26(H26), C29(H29), C30(H30), C32(H32), C33(H33)
;
_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
Cl1 Cl 1.43149(5) 0.69075(9) 0.62309(3) 0.0832(3) Uani 1 1 d . . . . .
O1 O 0.66582(12) 0.56821(13) 0.57455(8) 0.0530(4) Uani 1 1 d . . . . .
O2 O 0.72963(11) 0.38458(14) 0.60335(8) 0.0525(4) Uani 1 1 d . . . . .
C1 C 0.16137(16) 0.10724(18) 0.68944(10) 0.0403(4) Uani 1 1 d . . . . .
C2 C 0.17173(19) -0.0156(2) 0.69243(12) 0.0517(5) Uani 1 1 d . . . . .
H2 H 0.240305 -0.051941 0.686114 0.062 Uiso 1 1 calc R . . . .
C3 C 0.0823(2) -0.0859(2) 0.70461(13) 0.0622(6) Uani 1 1 d . . . . .
H3 H 0.090424 -0.169796 0.707016 0.075 Uiso 1 1 calc R . . . .
C4 C -0.0182(2) -0.0342(2) 0.71323(13) 0.0626(7) Uani 1 1 d . . . . .
H4 H -0.079523 -0.082475 0.720736 0.075 Uiso 1 1 calc R . . . .
C5 C -0.02911(18) 0.0872(2) 0.71090(12) 0.0583(6) Uani 1 1 d . . . . .
H5 H -0.098035 0.122952 0.716978 0.070 Uiso 1 1 calc R . . . .
C6 C 0.06005(17) 0.1575(2) 0.69970(11) 0.0479(5) Uani 1 1 d . . . . .
H6 H 0.052021 0.241502 0.699004 0.057 Uiso 1 1 calc R . . . .
C7 C 0.25733(15) 0.18553(17) 0.67906(10) 0.0397(4) Uani 1 1 d . . . . .
C8 C 0.28693(14) 0.28169(17) 0.73074(9) 0.0372(4) Uani 1 1 d . . . . .
C9 C 0.29442(16) 0.2571(2) 0.79940(10) 0.0446(5) Uani 1 1 d . . . . .
H9 H 0.280850 0.178658 0.813576 0.054 Uiso 1 1 calc R . . . .
C10 C 0.32174(16) 0.3467(2) 0.84780(10) 0.0484(5) Uani 1 1 d . . . . .
H10 H 0.328268 0.328708 0.894660 0.058 Uiso 1 1 calc R . . . .
C11 C 0.33906(17) 0.4603(2) 0.82744(11) 0.0494(5) Uani 1 1 d . . . . .
H11 H 0.357711 0.521196 0.860293 0.059 Uiso 1 1 calc R . . . .
C12 C 0.32953(17) 0.4869(2) 0.75925(11) 0.0485(5) Uani 1 1 d . . . . .
H12 H 0.340357 0.566127 0.745293 0.058 Uiso 1 1 calc R . . . .
C13 C 0.30427(16) 0.39823(18) 0.71159(10) 0.0417(4) Uani 1 1 d . . . . .
H13 H 0.298607 0.416968 0.664881 0.050 Uiso 1 1 calc R . . . .
C14 C 0.31387(15) 0.17014(17) 0.62708(10) 0.0394(4) Uani 1 1 d . . . . .
C15 C 0.27686(16) 0.08429(17) 0.57090(10) 0.0396(4) Uani 1 1 d . . . . .
C16 C 0.35272(19) 0.0018(2) 0.55335(12) 0.0520(5) Uani 1 1 d . . . . .
H16 H 0.427527 0.000161 0.577698 0.062 Uiso 1 1 calc R . . . .
C17 C 0.3209(2) -0.0783(2) 0.50077(12) 0.0605(6) Uani 1 1 d . . . . .
H17 H 0.373402 -0.135086 0.489925 0.073 Uiso 1 1 calc R . . . .
C18 C 0.2129(2) -0.0752(2) 0.46431(12) 0.0586(6) Uani 1 1 d . . . . .
H18 H 0.190469 -0.130681 0.428864 0.070 Uiso 1 1 calc R . . . .
C19 C 0.1386(2) 0.0081(2) 0.47941(11) 0.0560(6) Uani 1 1 d . . . . .
H19 H 0.065111 0.012087 0.453311 0.067 Uiso 1 1 calc R . . . .
C20 C 0.16954(17) 0.0865(2) 0.53251(10) 0.0463(5) Uani 1 1 d . . . . .
H20 H 0.116412 0.142961 0.542881 0.056 Uiso 1 1 calc R . . . .
C21 C 0.42020(15) 0.23501(17) 0.62255(10) 0.0392(4) Uani 1 1 d . . . . .
C22 C 0.50980(16) 0.23741(19) 0.67651(10) 0.0433(5) Uani 1 1 d . . . . .
H22 H 0.501596 0.201864 0.718412 0.052 Uiso 1 1 calc R . . . .
C23 C 0.61130(16) 0.29127(19) 0.66981(11) 0.0457(5) Uani 1 1 d . . . . .
H23 H 0.672516 0.291825 0.706580 0.055 Uiso 1 1 calc R . . . .
C24 C 0.62146(15) 0.34347(18) 0.60931(11) 0.0420(4) Uani 1 1 d . . . . .
C25 C 0.53355(17) 0.34596(19) 0.55570(10) 0.0444(5) Uani 1 1 d . . . . .
H25 H 0.541177 0.385054 0.514686 0.053 Uiso 1 1 calc R . . . .
C26 C 0.43378(16) 0.29046(19) 0.56261(10) 0.0433(5) Uani 1 1 d . . . . .
H26 H 0.373185 0.290315 0.525469 0.052 Uiso 1 1 calc R . . . .
C27 C 0.74175(16) 0.49853(18) 0.58542(10) 0.0430(4) Uani 1 1 d . . . . .
C28 C 0.86211(16) 0.52771(18) 0.58404(10) 0.0426(4) Uani 1 1 d . . . . .
C29 C 0.89039(18) 0.6453(2) 0.57680(12) 0.0502(5) Uani 1 1 d . . . . .
H29 H 0.833192 0.704281 0.570495 0.060 Uiso 1 1 calc R . . . .
C30 C 1.00146(18) 0.6778(2) 0.57868(12) 0.0512(5) Uani 1 1 d . . . . .
H30 H 1.020274 0.758976 0.573949 0.061 Uiso 1 1 calc R . . . .
C31 C 1.08553(16) 0.5922(2) 0.58745(11) 0.0481(5) Uani 1 1 d . . . . .
C32 C 1.05610(18) 0.4726(2) 0.59187(12) 0.0540(6) Uani 1 1 d . . . . .
H32 H 1.112574 0.413009 0.595553 0.065 Uiso 1 1 calc R . . . .
C33 C 0.94483(17) 0.4408(2) 0.59090(12) 0.0510(5) Uani 1 1 d . . . . .
H33 H 0.925246 0.359707 0.594924 0.061 Uiso 1 1 calc R . . . .
C34 C 1.20210(18) 0.6268(2) 0.59415(12) 0.0545(6) Uani 1 1 d . . . . .
C35 C 1.29765(19) 0.6547(2) 0.60468(12) 0.0602(6) 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
Cl1 C35 1.644(2) . ?
O1 C27 1.197(2) . ?
O2 C24 1.408(2) . ?
O2 C27 1.347(3) . ?
C1 C2 1.389(3) . ?
C1 C6 1.393(3) . ?
C1 C7 1.497(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.392(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.372(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.498(3) . ?
C7 C14 1.349(3) . ?
C8 C9 1.391(3) . ?
C8 C13 1.392(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.399(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.370(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.379(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.493(3) . ?
C14 C21 1.492(3) . ?
C15 C16 1.390(3) . ?
C15 C20 1.389(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.390(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.366(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.384(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.392(3) . ?
C21 C26 1.387(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.393(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.371(3) . ?
C24 C25 1.375(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.383(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.493(3) . ?
C28 C29 1.381(3) . ?
C28 C33 1.387(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.383(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.388(3) . ?
C31 C32 1.399(3) . ?
C31 C34 1.443(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.386(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.178(3) . ?

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
C27 O2 C24 118.66(16) . . ?
C2 C1 C6 118.23(19) . . ?
C2 C1 C7 121.74(18) . . ?
C6 C1 C7 119.96(18) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.1(2) . . ?
C5 C6 H6 119.5 . . ?
C1 C7 C8 115.36(16) . . ?
C14 C7 C1 122.39(18) . . ?
C14 C7 C8 122.25(17) . . ?
C9 C8 C7 120.47(18) . . ?
C9 C8 C13 118.19(18) . . ?
C13 C8 C7 121.31(17) . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.7(2) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.3(2) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.9(2) . . ?
C13 C12 H12 120.1 . . ?
C8 C13 H13 119.4 . . ?
C12 C13 C8 121.15(19) . . ?
C12 C13 H13 119.4 . . ?
C7 C14 C15 122.63(17) . . ?
C7 C14 C21 122.44(17) . . ?
C21 C14 C15 114.90(16) . . ?
C16 C15 C14 119.85(17) . . ?
C20 C15 C14 122.46(18) . . ?
C20 C15 C16 117.62(19) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.1(2) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.8(2) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(2) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 H20 119.4 . . ?
C19 C20 C15 121.2(2) . . ?
C19 C20 H20 119.4 . . ?
C22 C21 C14 121.61(18) . . ?
C26 C21 C14 120.13(17) . . ?
C26 C21 C22 118.20(18) . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.83(19) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 120.5 . . ?
C24 C23 C22 118.94(18) . . ?
C24 C23 H23 120.5 . . ?
C23 C24 O2 116.04(18) . . ?
C23 C24 C25 121.74(18) . . ?
C25 C24 O2 121.98(19) . . ?
C24 C25 H25 120.6 . . ?
C24 C25 C26 118.75(19) . . ?
C26 C25 H25 120.6 . . ?
C21 C26 H26 119.3 . . ?
C25 C26 C21 121.49(18) . . ?
C25 C26 H26 119.3 . . ?
O1 C27 O2 123.93(18) . . ?
O1 C27 C28 124.65(19) . . ?
O2 C27 C28 111.37(17) . . ?
C29 C28 C27 118.10(18) . . ?
C29 C28 C33 120.00(19) . . ?
C33 C28 C27 121.88(19) . . ?
C28 C29 H29 119.8 . . ?
C28 C29 C30 120.4(2) . . ?
C30 C29 H29 119.8 . . ?
C29 C30 H30 119.9 . . ?
C29 C30 C31 120.2(2) . . ?
C31 C30 H30 119.9 . . ?
C30 C31 C32 119.22(19) . . ?
C30 C31 C34 120.3(2) . . ?
C32 C31 C34 120.5(2) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 C31 120.2(2) . . ?
C33 C32 H32 119.9 . . ?
C28 C33 H33 120.1 . . ?
C32 C33 C28 119.9(2) . . ?
C32 C33 H33 120.1 . . ?
C35 C34 C31 175.1(2) . . ?
C34 C35 Cl1 177.2(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_200910_yfl_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2073602'
loop_
_audit_author_name
_audit_author_address
'Fulin Yang'
;Zhejiang University
China
;
_audit_update_record             
;
2021-03-27 deposited with the CCDC.	2021-12-14 downloaded from the CCDC.
;
_audit_creation_date             2020-09-10
_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         'C35 H23 Br O2'
_chemical_formula_sum            'C35 H23 Br O2'
_chemical_formula_weight         555.44
_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 0.0033 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      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                   12.175(7)
_cell_length_b                   11.191(8)
_cell_length_c                   20.212(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.916(19)
_cell_angle_gamma                90
_cell_volume                     2721(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6085
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.68
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.900
_shelx_estimated_absorpt_T_min   0.802
_exptl_absorpt_coefficient_mu    1.541
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1345 before and 0.0436 after correction.
The Ratio of minimum to maximum transmission is 0.8944.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.056
_diffrn_reflns_theta_min         2.441
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4183
_reflns_number_total             5930
_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       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.10'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_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         0.556
_refine_diff_density_min         -0.950
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5930
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.053
_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)+(0.0633P)²+1.6817P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1358
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23),
  C25(H25), C26(H26), C29(H29), C30(H30), C32(H32), C33(H33)
;
_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 1.43737(3) 0.30391(4) 0.62691(2) 0.06430(17) Uani 1 1 d . . . . .
O1 O 0.66588(17) 0.4316(2) 0.57255(11) 0.0467(5) Uani 1 1 d . . . . .
O2 O 0.72697(16) 0.6167(2) 0.60345(11) 0.0454(5) Uani 1 1 d . . . . .
C1 C 0.1713(3) 1.0232(3) 0.68948(16) 0.0479(8) Uani 1 1 d . . . . .
H1 H 0.239016 1.059336 0.682211 0.058 Uiso 1 1 calc R . . . .
C2 C 0.0826(3) 1.0947(3) 0.70172(17) 0.0550(9) Uani 1 1 d . . . . .
H2 H 0.090924 1.179117 0.703657 0.066 Uiso 1 1 calc R . . . .
C3 C -0.0169(3) 1.0435(4) 0.71101(17) 0.0603(10) Uani 1 1 d . . . . .
H3 H -0.077558 1.092718 0.718117 0.072 Uiso 1 1 calc R . . . .
C4 C -0.0285(3) 0.9202(4) 0.70997(16) 0.0532(9) Uani 1 1 d . . . . .
H4 H -0.096793 0.884662 0.716614 0.064 Uiso 1 1 calc R . . . .
C5 C 0.0602(2) 0.8492(3) 0.69921(15) 0.0430(7) Uani 1 1 d . . . . .
H5 H 0.052231 0.764782 0.699546 0.052 Uiso 1 1 calc R . . . .
C6 C 0.1610(2) 0.8986(3) 0.68785(13) 0.0359(7) Uani 1 1 d . . . . .
C7 C 0.2560(2) 0.8191(3) 0.67783(14) 0.0340(6) Uani 1 1 d . . . . .
C8 C 0.2844(2) 0.7240(3) 0.72955(13) 0.0329(6) Uani 1 1 d . . . . .
C9 C 0.2903(2) 0.7507(3) 0.79741(14) 0.0388(7) Uani 1 1 d . . . . .
H9 H 0.275826 0.829844 0.810779 0.047 Uiso 1 1 calc R . . . .
C10 C 0.3174(2) 0.6615(3) 0.84618(15) 0.0418(8) Uani 1 1 d . . . . .
H10 H 0.322282 0.680485 0.892355 0.050 Uiso 1 1 calc R . . . .
C11 C 0.3369(2) 0.5466(3) 0.82681(15) 0.0425(7) Uani 1 1 d . . . . .
H11 H 0.356140 0.486424 0.859743 0.051 Uiso 1 1 calc R . . . .
C12 C 0.3285(2) 0.5181(3) 0.75955(15) 0.0421(7) Uani 1 1 d . . . . .
H12 H 0.340201 0.438146 0.746441 0.050 Uiso 1 1 calc R . . . .
C13 C 0.3031(2) 0.6060(3) 0.71134(14) 0.0367(7) Uani 1 1 d . . . . .
H13 H 0.298244 0.585858 0.665319 0.044 Uiso 1 1 calc R . . . .
C14 C 0.3124(2) 0.8330(3) 0.62565(14) 0.0341(6) Uani 1 1 d . . . . .
C15 C 0.2763(2) 0.9174(3) 0.56883(13) 0.0337(6) Uani 1 1 d . . . . .
C16 C 0.3522(3) 0.9986(3) 0.54967(16) 0.0451(7) Uani 1 1 d . . . . .
H16 H 0.426563 0.999525 0.572382 0.054 Uiso 1 1 calc R . . . .
C17 C 0.3195(3) 1.0787(3) 0.49721(17) 0.0529(9) Uani 1 1 d . . . . .
H17 H 0.371034 1.135676 0.485543 0.063 Uiso 1 1 calc R . . . .
C18 C 0.2127(3) 1.0753(3) 0.46228(16) 0.0525(9) Uani 1 1 d . . . . .
H18 H 0.190857 1.129824 0.426645 0.063 Uiso 1 1 calc R . . . .
C19 C 0.1384(3) 0.9932(3) 0.47910(16) 0.0496(8) Uani 1 1 d . . . . .
H19 H 0.065527 0.989630 0.454329 0.060 Uiso 1 1 calc R . . . .
C20 C 0.1691(2) 0.9148(3) 0.53234(14) 0.0406(7) Uani 1 1 d . . . . .
H20 H 0.116441 0.858992 0.543945 0.049 Uiso 1 1 calc R . . . .
C21 C 0.4186(2) 0.7676(3) 0.62118(13) 0.0332(6) Uani 1 1 d . . . . .
C22 C 0.5072(2) 0.7681(3) 0.67417(14) 0.0378(7) Uani 1 1 d . . . . .
H22 H 0.498616 0.806330 0.715020 0.045 Uiso 1 1 calc R . . . .
C23 C 0.6078(2) 0.7137(3) 0.66808(15) 0.0405(7) Uani 1 1 d . . . . .
H23 H 0.667670 0.714955 0.704296 0.049 Uiso 1 1 calc R . . . .
C24 C 0.6193(2) 0.6581(3) 0.60896(15) 0.0365(7) Uani 1 1 d . . . . .
C25 C 0.5327(2) 0.6533(3) 0.55608(14) 0.0373(7) Uani 1 1 d . . . . .
H25 H 0.541122 0.612242 0.516032 0.045 Uiso 1 1 calc R . . . .
C26 C 0.4335(2) 0.7091(3) 0.56229(14) 0.0376(7) Uani 1 1 d . . . . .
H26 H 0.374256 0.707599 0.525678 0.045 Uiso 1 1 calc R . . . .
C27 C 0.7407(2) 0.5025(3) 0.58461(14) 0.0373(7) Uani 1 1 d . . . . .
C28 C 0.8603(2) 0.4742(3) 0.58345(14) 0.0365(7) Uani 1 1 d . . . . .
C29 C 0.8888(3) 0.3568(3) 0.57328(16) 0.0447(7) Uani 1 1 d . . . . .
H29 H 0.832126 0.297885 0.564885 0.054 Uiso 1 1 calc R . . . .
C30 C 0.9990(3) 0.3238(3) 0.57518(17) 0.0473(8) Uani 1 1 d . . . . .
H30 H 1.017550 0.242812 0.568217 0.057 Uiso 1 1 calc R . . . .
C31 C 1.0830(2) 0.4102(3) 0.58737(15) 0.0422(7) Uani 1 1 d . . . . .
C32 C 1.0535(3) 0.5296(3) 0.59452(18) 0.0511(9) Uani 1 1 d . . . . .
H32 H 1.109401 0.589588 0.600391 0.061 Uiso 1 1 calc R . . . .
C33 C 0.9424(2) 0.5612(3) 0.59309(17) 0.0474(8) Uani 1 1 d . . . . .
H33 H 0.922839 0.642324 0.598718 0.057 Uiso 1 1 calc R . . . .
C34 C 1.1987(3) 0.3750(3) 0.59466(16) 0.0464(8) Uani 1 1 d . . . . .
C35 C 1.2921(3) 0.3467(3) 0.60507(17) 0.0511(9) 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 C35 1.819(3) . ?
O1 C27 1.204(4) . ?
O2 C24 1.411(3) . ?
O2 C27 1.351(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.396(5) . ?
C1 C6 1.400(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.398(4) . ?
C6 C7 1.498(4) . ?
C7 C8 1.494(4) . ?
C7 C14 1.353(4) . ?
C8 C9 1.395(4) . ?
C8 C13 1.399(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.406(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.375(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.499(4) . ?
C14 C21 1.501(4) . ?
C15 C16 1.392(4) . ?
C15 C20 1.397(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.398(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.368(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.394(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.398(4) . ?
C21 C26 1.395(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.389(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.374(4) . ?
C24 C25 1.381(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.382(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.493(4) . ?
C28 C29 1.382(5) . ?
C28 C33 1.387(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.387(4) . ?
C30 H30 0.9500 . ?
C30 C31 1.400(5) . ?
C31 C32 1.398(5) . ?
C31 C34 1.448(4) . ?
C32 H32 0.9500 . ?
C32 C33 1.394(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.168(4) . ?

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
C27 O2 C24 119.3(2) . . ?
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.4(3) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.7(3) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C7 121.8(3) . . ?
C5 C6 C1 117.9(3) . . ?
C5 C6 C7 120.3(3) . . ?
C8 C7 C6 115.4(2) . . ?
C14 C7 C6 122.2(3) . . ?
C14 C7 C8 122.5(3) . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 C13 118.4(3) . . ?
C13 C8 C7 121.2(2) . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.5(3) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.8(3) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.1(3) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 H13 119.6 . . ?
C12 C13 C8 120.9(3) . . ?
C12 C13 H13 119.6 . . ?
C7 C14 C15 123.1(3) . . ?
C7 C14 C21 122.4(3) . . ?
C15 C14 C21 114.5(2) . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 C20 118.2(3) . . ?
C20 C15 C14 122.0(3) . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 H20 119.6 . . ?
C19 C20 C15 120.7(3) . . ?
C19 C20 H20 119.6 . . ?
C22 C21 C14 121.5(3) . . ?
C26 C21 C14 120.5(2) . . ?
C26 C21 C22 118.0(3) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 C21 121.1(3) . . ?
C23 C22 H22 119.5 . . ?
C22 C23 H23 120.5 . . ?
C24 C23 C22 119.1(3) . . ?
C24 C23 H23 120.5 . . ?
C23 C24 O2 116.0(3) . . ?
C23 C24 C25 121.5(3) . . ?
C25 C24 O2 122.2(3) . . ?
C24 C25 H25 120.5 . . ?
C24 C25 C26 119.0(3) . . ?
C26 C25 H25 120.5 . . ?
C21 C26 H26 119.3 . . ?
C25 C26 C21 121.4(3) . . ?
C25 C26 H26 119.3 . . ?
O1 C27 O2 123.8(3) . . ?
O1 C27 C28 124.5(3) . . ?
O2 C27 C28 111.6(3) . . ?
C29 C28 C27 118.2(3) . . ?
C29 C28 C33 119.7(3) . . ?
C33 C28 C27 122.1(3) . . ?
C28 C29 H29 119.6 . . ?
C28 C29 C30 120.9(3) . . ?
C30 C29 H29 119.6 . . ?
C29 C30 H30 120.0 . . ?
C29 C30 C31 119.9(3) . . ?
C31 C30 H30 120.0 . . ?
C30 C31 C34 120.2(3) . . ?
C32 C31 C30 119.1(3) . . ?
C32 C31 C34 120.7(3) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 C31 120.3(3) . . ?
C33 C32 H32 119.9 . . ?
C28 C33 C32 120.1(3) . . ?
C28 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C35 C34 C31 175.5(3) . . ?
C34 C35 Br1 176.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
