# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_JCZ03_4
_database_code_depnum_ccdc_archive 'CCDC 2009014'
loop_
_audit_author_name
_audit_author_address
'Chengzhou Jiang'
;Nanjing Tech University
China
;
_audit_update_record             
;
2020-06-10 deposited with the CCDC.	2021-04-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H19 Br O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         455.33

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   14.3651(12)
_cell_length_b                   10.7385(10)
_cell_length_c                   13.3772(13)
_cell_angle_alpha                90
_cell_angle_beta                 94.475(6)
_cell_angle_gamma                90
_cell_volume                     2057.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5498
_cell_measurement_theta_min      2.7595
_cell_measurement_theta_max      25.0700
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.140
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928

_exptl_absorpt_coefficient_mu    2.020
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
'TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1'
_exptl_absorpt_correction_T_min  0.44
_exptl_absorpt_correction_T_max  0.77

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            6983
_diffrn_reflns_av_R_equivalents  0.0981
_diffrn_reflns_av_unetI/netI     0.1205
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         25.11
_diffrn_reflns_theta_full        25.11
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;

Refined as a 3-component twin.
;

_reflns_number_total             3648
_reflns_number_gt                2343
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1379
_refine_ls_R_factor_gt           0.0868
_refine_ls_wR_factor_gt          0.1579
_refine_ls_wR_factor_ref         0.1735
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_restrained_S_all      1.185
_refine_ls_number_reflns         3648
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0485P)²+1.2082P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.361
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2018)'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2018)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.00353(5) 0.32077(7) 0.05613(5) 0.0617(3) Uani d . . . 1 . .
C C1 0.5316(4) 0.2684(6) 1.0105(4) 0.0392(15) Uani d . . . 1 . .
H H1 0.468587 0.262338 0.989211 0.047 Uiso calc U . R 1 . .
C C2 0.5679(4) 0.1901(6) 1.0842(4) 0.0494(17) Uani d . . . 1 . .
H H2 0.529753 0.131441 1.111762 0.059 Uiso calc U . R 1 . .
C C3 0.6618(5) 0.1977(7) 1.1179(5) 0.0543(19) Uani d . . . 1 . .
H H3 0.686758 0.143892 1.167423 0.065 Uiso calc U . R 1 . .
C C4 0.7165(4) 0.2845(6) 1.0779(4) 0.0453(17) Uani d . . . 1 . .
H H4 0.778871 0.290986 1.101984 0.054 Uiso calc U . R 1 . .
C C5 0.6817(4) 0.3644(6) 1.0016(4) 0.0372(15) Uani d . . . 1 . .
C C6 0.5867(4) 0.3577(5) 0.9662(4) 0.0329(14) Uani d . . . 1 . .
C C7 0.5520(3) 0.4407(5) 0.8859(4) 0.0289(13) Uani d . . . 1 . .
C C8 0.4589(3) 0.4417(5) 0.8461(4) 0.0306(13) Uani d . . . 1 . .
H H8 0.416825 0.387323 0.872461 0.037 Uiso calc U . R 1 . .
C C9 0.4271(3) 0.5205(5) 0.7691(4) 0.0276(12) Uani d . . . 1 . .
C C10 0.4899(4) 0.6017(6) 0.7291(5) 0.0420(15) Uani d . . . 1 . .
H H10 0.469504 0.65427 0.676657 0.05 Uiso calc U . R 1 . .
C C11 0.5813(4) 0.6052(6) 0.7663(5) 0.0431(16) Uani d . . . 1 . .
H H11 0.622337 0.660827 0.739523 0.052 Uiso calc U . R 1 . .
C C12 0.6138(4) 0.5251(5) 0.8448(4) 0.0347(14) Uani d . . . 1 . .
C C13 0.7098(4) 0.5301(6) 0.8832(5) 0.0448(16) Uani d . . . 1 . .
H H13 0.750461 0.586022 0.856202 0.054 Uiso calc U . R 1 . .
C C14 0.7407(4) 0.4544(6) 0.9575(5) 0.0453(16) Uani d . . . 1 . .
H H14 0.802981 0.459873 0.981899 0.054 Uiso calc U . R 1 . .
C C15 0.3268(4) 0.5149(5) 0.7327(4) 0.0334(13) Uani d . . . 1 . .
C C16 0.2939(3) 0.5920(5) 0.6418(4) 0.0354(14) Uani d . . . 1 . .
H H16A 0.307525 0.678887 0.656325 0.042 Uiso calc U . R 1 . .
H H16B 0.329433 0.567782 0.586165 0.042 Uiso calc U . R 1 . .
C C17 0.1924(3) 0.5799(5) 0.6099(4) 0.0310(13) Uani d . . . 1 . .
C C18 0.1295(4) 0.6650(6) 0.6572(4) 0.0401(15) Uani d . . . 1 . .
H H18 0.065918 0.655682 0.639619 0.048 Uiso calc U . R 1 . .
C C19 0.1532(4) 0.5027(5) 0.5399(4) 0.0346(14) Uani d . . . 1 . .
H H19 0.088826 0.510874 0.52824 0.041 Uiso calc U . R 1 . .
C C20 0.1946(4) 0.4089(5) 0.4795(4) 0.0374(14) Uani d . . . 1 . .
C C21 0.1489(3) 0.3883(5) 0.3761(4) 0.0319(13) Uani d . . . 1 . .
C C22 0.1100(3) 0.4864(5) 0.3198(4) 0.0346(14) Uani d . . . 1 . .
H H22 0.113009 0.566602 0.346133 0.042 Uiso calc U . R 1 . .
C C23 0.0667(4) 0.4666(6) 0.2248(4) 0.0381(14) Uani d . . . 1 . .
H H23 0.0407 0.532903 0.187605 0.046 Uiso calc U . R 1 . .
C C24 0.0625(4) 0.3495(5) 0.1866(4) 0.0355(14) Uani d . . . 1 . .
C C25 0.1013(4) 0.2494(6) 0.2393(4) 0.0418(15) Uani d . . . 1 . .
H H25 0.098919 0.169863 0.211668 0.05 Uiso calc U . R 1 . .
C C26 0.1439(4) 0.2698(6) 0.3340(4) 0.0393(14) Uani d . . . 1 . .
H H26 0.169738 0.202818 0.370488 0.047 Uiso calc U . R 1 . .
C C27 0.2681(5) 0.3403(7) 0.5127(5) 0.067(2) Uani d . . . 1 . .
H H27A 0.295232 0.351732 0.577464 0.08 Uiso calc U . R 1 . .
H H27B 0.292233 0.281057 0.47105 0.08 Uiso calc U . R 1 . .
O O1 0.2727(3) 0.4486(4) 0.7727(3) 0.0591(14) Uani d . . . 1 . .
O O2 0.1518(3) 0.7462(4) 0.7168(3) 0.0609(13) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C24 . 1.904(5) ?
C1 C2 . 1.368(8) ?
C1 C6 . 1.404(8) ?
C1 H1 . 0.93 ?
C2 C3 . 1.390(9) ?
C2 H2 . 0.93 ?
C3 C4 . 1.356(9) ?
C3 H3 . 0.93 ?
C4 C5 . 1.396(8) ?
C4 H4 . 0.93 ?
C5 C6 . 1.411(7) ?
C5 C14 . 1.442(8) ?
C6 C7 . 1.454(7) ?
C7 C8 . 1.400(7) ?
C7 C12 . 1.410(7) ?
C8 C9 . 1.383(7) ?
C8 H8 . 0.93 ?
C9 C10 . 1.391(8) ?
C9 C15 . 1.485(7) ?
C10 C11 . 1.368(7) ?
C10 H10 . 0.93 ?
C11 C12 . 1.408(8) ?
C11 H11 . 0.93 ?
C12 C13 . 1.435(7) ?
C13 C14 . 1.333(8) ?
C13 H13 . 0.93 ?
C14 H14 . 0.93 ?
C15 O1 . 1.209(6) ?
C15 C16 . 1.517(7) ?
C16 C17 . 1.493(7) ?
C16 H16A . 0.97 ?
C16 H16B . 0.97 ?
C17 C19 . 1.341(7) ?
C17 C18 . 1.464(8) ?
C18 O2 . 1.208(7) ?
C18 H18 . 0.93 ?
C19 C20 . 1.448(8) ?
C19 H19 . 0.93 ?
C20 C27 . 1.335(8) ?
C20 C21 . 1.500(7) ?
C21 C22 . 1.386(7) ?
C21 C26 . 1.392(8) ?
C22 C23 . 1.388(7) ?
C22 H22 . 0.93 ?
C23 C24 . 1.357(7) ?
C23 H23 . 0.93 ?
C24 C25 . 1.380(8) ?
C25 C26 . 1.380(8) ?
C25 H25 . 0.93 ?
C26 H26 . 0.93 ?
C27 H27A . 0.93 ?
C27 H27B . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 121.9(5) ?
C2 C1 H1 . . 119.1 ?
C6 C1 H1 . . 119.1 ?
C1 C2 C3 . . 120.2(6) ?
C1 C2 H2 . . 119.9 ?
C3 C2 H2 . . 119.9 ?
C4 C3 C2 . . 119.4(6) ?
C4 C3 H3 . . 120.3 ?
C2 C3 H3 . . 120.3 ?
C3 C4 C5 . . 121.6(6) ?
C3 C4 H4 . . 119.2 ?
C5 C4 H4 . . 119.2 ?
C4 C5 C6 . . 119.8(6) ?
C4 C5 C14 . . 121.5(5) ?
C6 C5 C14 . . 118.7(5) ?
C1 C6 C5 . . 117.1(5) ?
C1 C6 C7 . . 124.0(5) ?
C5 C6 C7 . . 118.9(5) ?
C8 C7 C12 . . 117.3(5) ?
C8 C7 C6 . . 123.2(5) ?
C12 C7 C6 . . 119.5(5) ?
C9 C8 C7 . . 122.6(5) ?
C9 C8 H8 . . 118.7 ?
C7 C8 H8 . . 118.7 ?
C8 C9 C10 . . 118.9(5) ?
C8 C9 C15 . . 118.4(5) ?
C10 C9 C15 . . 122.8(5) ?
C11 C10 C9 . . 120.7(5) ?
C11 C10 H10 . . 119.6 ?
C9 C10 H10 . . 119.6 ?
C10 C11 C12 . . 120.4(5) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C11 C12 C7 . . 120.1(5) ?
C11 C12 C13 . . 119.8(5) ?
C7 C12 C13 . . 120.1(5) ?
C14 C13 C12 . . 119.9(6) ?
C14 C13 H13 . . 120.0 ?
C12 C13 H13 . . 120.0 ?
C13 C14 C5 . . 122.8(5) ?
C13 C14 H14 . . 118.6 ?
C5 C14 H14 . . 118.6 ?
O1 C15 C9 . . 121.3(5) ?
O1 C15 C16 . . 120.4(5) ?
C9 C15 C16 . . 118.3(5) ?
C17 C16 C15 . . 114.7(5) ?
C17 C16 H16A . . 108.6 ?
C15 C16 H16A . . 108.6 ?
C17 C16 H16B . . 108.6 ?
C15 C16 H16B . . 108.6 ?
H16A C16 H16B . . 107.6 ?
C19 C17 C18 . . 116.6(5) ?
C19 C17 C16 . . 126.9(5) ?
C18 C17 C16 . . 116.4(5) ?
O2 C18 C17 . . 126.5(5) ?
O2 C18 H18 . . 116.8 ?
C17 C18 H18 . . 116.8 ?
C17 C19 C20 . . 130.7(5) ?
C17 C19 H19 . . 114.7 ?
C20 C19 H19 . . 114.7 ?
C27 C20 C19 . . 123.1(5) ?
C27 C20 C21 . . 120.2(5) ?
C19 C20 C21 . . 116.6(5) ?
C22 C21 C26 . . 118.0(5) ?
C22 C21 C20 . . 121.2(5) ?
C26 C21 C20 . . 120.8(5) ?
C21 C22 C23 . . 120.9(5) ?
C21 C22 H22 . . 119.5 ?
C23 C22 H22 . . 119.5 ?
C24 C23 C22 . . 119.4(5) ?
C24 C23 H23 . . 120.3 ?
C22 C23 H23 . . 120.3 ?
C23 C24 C25 . . 121.7(5) ?
C23 C24 Br1 . . 119.9(4) ?
C25 C24 Br1 . . 118.4(4) ?
C24 C25 C26 . . 118.6(5) ?
C24 C25 H25 . . 120.7 ?
C26 C25 H25 . . 120.7 ?
C25 C26 C21 . . 121.4(5) ?
C25 C26 H26 . . 119.3 ?
C21 C26 H26 . . 119.3 ?
C20 C27 H27A . . 120.0 ?
C20 C27 H27B . . 120.0 ?
H27A C27 H27B . . 120.0 ?

