# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2104267097_0m
_database_code_depnum_ccdc_archive 'CCDC 2132066'
loop_
_audit_author_name
_audit_author_address
'Chaojie Wang'
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2022-01-03 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;
_audit_creation_date             2021-04-28
_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         'C24 H19 Br O4'
_chemical_formula_sum            'C24 H19 Br O4'
_chemical_formula_weight         451.30
_chemical_absolute_configuration rmad
_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 0.0148 0.0070 '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 -0.9502 1.0410 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   6.76460(10)
_cell_length_b                   16.0325(3)
_cell_length_c                   19.2455(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2087.24(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9843
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      54.91
_cell_measurement_theta_min      4.00
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.907
_exptl_absorpt_coefficient_mu    1.986
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1640 before and 0.0691 after correction. The Ratio of minimum to maximum transmission is 0.6789. 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    1.436
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22356
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.909
_diffrn_reflns_theta_min         3.121
_diffrn_ambient_temperature      193.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3872
_reflns_number_total             3955
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 1616 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.046(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3955
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0249
_refine_ls_restrained_S_all      1.072
_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)+(0.0328P)²+0.4622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0632
_refine_ls_wR_factor_ref         0.0638
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C20(H20), C21(H21), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.73212(5) 0.62196(2) 0.42576(2) 0.04445(12) Uani 1 1 d . . . . .
O1 O -0.0040(3) 0.41105(12) 0.60879(9) 0.0284(4) Uani 1 1 d . . . . .
O2 O 0.1919(4) 0.67586(13) 0.86211(13) 0.0499(6) Uani 1 1 d . . . . .
H2 H 0.074880 0.693418 0.861943 0.075 Uiso 1 1 calc GR . . . .
O3 O 0.2049(3) 0.22620(11) 0.63469(9) 0.0370(5) Uani 1 1 d . . . . .
O4 O 0.4247(3) 0.27598(11) 0.55940(9) 0.0346(5) Uani 1 1 d . . . . .
C1 C 0.2483(4) 0.36139(12) 0.72525(10) 0.0210(4) Uani 1 1 d . . . . .
H1 H 0.109152 0.340781 0.721719 0.025 Uiso 1 1 calc R . . . .
C2 C 0.3252(3) 0.36723(14) 0.64936(11) 0.0197(5) Uani 1 1 d . . . . .
C3 C 0.5248(4) 0.41106(15) 0.63499(12) 0.0216(5) Uani 1 1 d . . . . .
H3A H 0.566613 0.444554 0.675628 0.026 Uiso 1 1 calc R . . . .
H3B H 0.629111 0.369654 0.624388 0.026 Uiso 1 1 calc R . . . .
C4 C 0.4863(4) 0.46647(13) 0.57297(12) 0.0212(5) Uani 1 1 d . . . . .
C5 C 0.6238(4) 0.51043(15) 0.53386(12) 0.0246(5) Uani 1 1 d . . . . .
H5 H 0.761103 0.507936 0.543997 0.030 Uiso 1 1 calc R . . . .
C6 C 0.5517(4) 0.55813(16) 0.47938(13) 0.0280(5) Uani 1 1 d . . . . .
C7 C 0.3523(4) 0.56288(17) 0.46251(14) 0.0329(6) Uani 1 1 d . . . . .
H7 H 0.309389 0.595733 0.424290 0.039 Uiso 1 1 calc R . . . .
C8 C 0.2178(4) 0.51929(16) 0.50202(12) 0.0294(5) Uani 1 1 d . . . . .
H8 H 0.080535 0.521869 0.491837 0.035 Uiso 1 1 calc R . . . .
C9 C 0.2872(4) 0.47119(14) 0.55734(11) 0.0225(5) Uani 1 1 d . . . . .
C10 C 0.1743(4) 0.41817(14) 0.60446(12) 0.0220(5) Uani 1 1 d . . . . .
C11 C 0.3137(4) 0.28089(14) 0.61562(12) 0.0227(5) Uani 1 1 d . . . . .
C12 C 0.4139(6) 0.19912(17) 0.51887(15) 0.0440(8) Uani 1 1 d . . . . .
H12A H 0.423241 0.212420 0.469276 0.066 Uiso 1 1 calc GR . . . .
H12B H 0.287956 0.171062 0.528151 0.066 Uiso 1 1 calc GR . . . .
H12C H 0.523362 0.162284 0.531979 0.066 Uiso 1 1 calc GR . . . .
C13 C 0.3558(4) 0.29878(14) 0.77124(12) 0.0249(5) Uani 1 1 d . . . . .
C14 C 0.5506(4) 0.27531(17) 0.76280(14) 0.0328(6) Uani 1 1 d . . . . .
H14 H 0.625109 0.297616 0.725323 0.039 Uiso 1 1 calc R . . . .
C15 C 0.6394(5) 0.21923(16) 0.80859(15) 0.0378(7) Uani 1 1 d . . . . .
H15 H 0.773277 0.203245 0.801886 0.045 Uiso 1 1 calc R . . . .
C16 C 0.5341(6) 0.18715(19) 0.86319(16) 0.0468(8) Uani 1 1 d . . . . .
H16 H 0.594897 0.149460 0.894713 0.056 Uiso 1 1 calc R . . . .
C17 C 0.3386(6) 0.2100(2) 0.87209(18) 0.0559(10) Uani 1 1 d . . . . .
H17 H 0.264637 0.187781 0.909740 0.067 Uiso 1 1 calc R . . . .
C18 C 0.2505(5) 0.26510(17) 0.82647(14) 0.0405(7) Uani 1 1 d . . . . .
H18 H 0.115958 0.280180 0.832939 0.049 Uiso 1 1 calc R . . . .
C19 C 0.2353(4) 0.44672(13) 0.76063(11) 0.0238(5) Uani 1 1 d . . . . .
C20 C 0.0559(4) 0.48861(17) 0.76304(14) 0.0316(6) Uani 1 1 d . . . . .
H20 H -0.056634 0.464629 0.741278 0.038 Uiso 1 1 calc R . . . .
C21 C 0.0376(5) 0.56493(17) 0.79664(15) 0.0369(6) Uani 1 1 d . . . . .
H21 H -0.086630 0.592546 0.798072 0.044 Uiso 1 1 calc R . . . .
C22 C 0.2008(4) 0.60037(16) 0.82791(14) 0.0342(6) Uani 1 1 d . . . . .
C23 C 0.3811(5) 0.56050(17) 0.82611(14) 0.0329(6) Uani 1 1 d . . . . .
H23 H 0.493458 0.585363 0.847274 0.039 Uiso 1 1 calc R . . . .
C24 C 0.3977(4) 0.48349(16) 0.79306(13) 0.0267(5) Uani 1 1 d . . . . .
H24 H 0.521611 0.455598 0.792622 0.032 Uiso 1 1 calc R . . . .


_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 C6 1.898(2) . ?
O1 C10 1.214(3) . ?
O2 H2 0.8400 . ?
O2 C22 1.379(3) . ?
O3 C11 1.202(3) . ?
O4 C11 1.319(3) . ?
O4 C12 1.460(3) . ?
C1 H1 1.0000 . ?
C1 C2 1.553(3) . ?
C1 C13 1.523(3) . ?
C1 C19 1.531(3) . ?
C2 C3 1.547(3) . ?
C2 C10 1.567(3) . ?
C2 C11 1.531(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.511(3) . ?
C4 C5 1.389(3) . ?
C4 C9 1.382(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(3) . ?
C6 C7 1.390(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.376(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.396(3) . ?
C9 C10 1.459(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.380(4) . ?
C13 C18 1.389(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.395(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.370(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.383(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(4) . ?
C19 C24 1.395(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.389(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.380(4) . ?
C22 C23 1.378(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.393(4) . ?
C24 H24 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
C22 O2 H2 109.5 . . ?
C11 O4 C12 117.4(2) . . ?
C2 C1 H1 105.7 . . ?
C13 C1 H1 105.7 . . ?
C13 C1 C2 115.25(19) . . ?
C13 C1 C19 110.98(18) . . ?
C19 C1 H1 105.7 . . ?
C19 C1 C2 112.56(17) . . ?
C1 C2 C10 109.40(18) . . ?
C3 C2 C1 119.18(19) . . ?
C3 C2 C10 103.49(18) . . ?
C11 C2 C1 109.11(17) . . ?
C11 C2 C3 112.26(19) . . ?
C11 C2 C10 101.80(17) . . ?
C2 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.8 . . ?
C4 C3 C2 104.93(19) . . ?
C4 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
C5 C4 C3 127.7(2) . . ?
C9 C4 C3 111.9(2) . . ?
C9 C4 C5 120.5(2) . . ?
C4 C5 H5 121.5 . . ?
C6 C5 C4 117.0(2) . . ?
C6 C5 H5 121.5 . . ?
C5 C6 Br1 118.9(2) . . ?
C5 C6 C7 123.2(2) . . ?
C7 C6 Br1 117.88(19) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 119.0(2) . . ?
C8 C7 H7 120.5 . . ?
C7 C8 H8 120.7 . . ?
C7 C8 C9 118.7(2) . . ?
C9 C8 H8 120.7 . . ?
C4 C9 C8 121.6(2) . . ?
C4 C9 C10 110.0(2) . . ?
C8 C9 C10 128.3(2) . . ?
O1 C10 C2 124.1(2) . . ?
O1 C10 C9 128.1(2) . . ?
C9 C10 C2 107.8(2) . . ?
O3 C11 O4 123.7(2) . . ?
O3 C11 C2 124.1(2) . . ?
O4 C11 C2 111.91(19) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C1 124.6(2) . . ?
C14 C13 C18 118.3(3) . . ?
C18 C13 C1 117.1(3) . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.8(3) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.5(3) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 119.5 . . ?
C17 C18 C13 120.9(3) . . ?
C17 C18 H18 119.5 . . ?
C20 C19 C1 119.9(2) . . ?
C20 C19 C24 118.0(2) . . ?
C24 C19 C1 122.1(2) . . ?
C19 C20 H20 119.3 . . ?
C19 C20 C21 121.3(3) . . ?
C21 C20 H20 119.3 . . ?
C20 C21 H21 120.2 . . ?
C22 C21 C20 119.6(3) . . ?
C22 C21 H21 120.2 . . ?
O2 C22 C21 122.3(3) . . ?
C23 C22 O2 117.2(3) . . ?
C23 C22 C21 120.4(2) . . ?
C22 C23 H23 120.2 . . ?
C22 C23 C24 119.6(3) . . ?
C24 C23 H23 120.2 . . ?
C19 C24 H24 119.5 . . ?
C23 C24 C19 121.0(2) . . ?
C23 C24 H24 119.5 . . ?

_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_a
_database_code_depnum_ccdc_archive 'CCDC 2165881'
loop_
_audit_author_name
_audit_author_address
'Suosuo Qi'
;zhejiang university of technology
China
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;
_audit_creation_date             2022-03-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H18 Cl O4, C H4 O'
_chemical_formula_sum            'C25 H22 Cl O5'
_chemical_formula_weight         437.87
_chemical_absolute_configuration ad
_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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.1420(11)
_cell_length_b                   11.4280(15)
_cell_length_c                   22.2670(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2326.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    359
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      43.309
_cell_measurement_theta_min      13.148
_shelx_estimated_absorpt_T_max   0.847
_shelx_estimated_absorpt_T_min   0.820
_exptl_absorpt_coefficient_mu    1.723
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.4996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1515 before and 0.0996 after correction.
The Ratio of minimum to maximum transmission is 0.6623.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             916
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1189
_diffrn_reflns_av_unetI/netI     0.0858
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20073
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.210
_diffrn_reflns_theta_min         5.230
_diffrn_ambient_temperature      173.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_type              'Incoatec I\ms DIAMOND'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.906
_reflns_number_gt                3056
_reflns_number_total             4711
_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 V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX3 V2019.11-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 959 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.080(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4711
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0690
_refine_ls_restrained_S_all      0.981
_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)+(0.1263P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1784
_refine_ls_wR_factor_ref         0.2075
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C6(H6), C13(H13), C12(H12), C5(H5), C2(H2), C9(H9), C19(H19),
 C3(H3), C11(H11), C22(H22), C10(H10), C21(H21)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C25(H25A,H25B,H25C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_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 -1.0902(3) -0.46699(18) -0.03129(9) 0.1279(8) Uani 1 1 d . . . . .
O2 O -0.4890(4) -0.1391(3) -0.12338(17) 0.0725(10) Uani 1 1 d . . . . .
O3 O -0.4949(4) 0.0457(3) -0.1575(2) 0.0860(12) Uani 1 1 d . . . . .
O5 O -0.8011(5) 0.0723(3) -0.09501(19) 0.0827(11) Uani 1 1 d . . . . .
O1 O -0.3982(6) -0.0468(4) -0.43277(16) 0.0914(13) Uani 1 1 d . . . . .
H1 H -0.379916 -0.116968 -0.441085 0.137 Uiso 1 1 calc R U . . .
C7 C -0.7528(5) 0.0025(4) -0.2237(2) 0.0565(10) Uani 1 1 d . . . . .
H7 H -0.734974 0.085536 -0.211562 0.068 Uiso 1 1 calc R U . . .
C17 C -0.7540(5) -0.2064(4) -0.1715(2) 0.0576(11) Uani 1 1 d . . . . .
H17 H -0.722297 -0.260804 -0.201003 0.069 Uiso 1 1 calc R U . . .
C1 C -0.4826(6) -0.0419(4) -0.3825(2) 0.0651(12) Uani 1 1 d . . . . .
C4 C -0.6544(5) -0.0187(4) -0.2783(2) 0.0567(10) Uani 1 1 d . . . . .
C6 C -0.5120(6) -0.1405(4) -0.3464(2) 0.0625(11) Uani 1 1 d . . . . .
H6 H -0.475400 -0.215442 -0.357199 0.075 Uiso 1 1 calc R U . . .
C23 C -0.8824(5) -0.1279(4) -0.0866(2) 0.0598(11) Uani 1 1 d . . . . .
C18 C -0.8540(5) -0.2297(4) -0.1193(2) 0.0562(10) Uani 1 1 d . . . . .
C8 C -0.9152(5) -0.0047(4) -0.2384(2) 0.0614(11) Uani 1 1 d . . . . .
C13 C -1.0140(5) 0.0712(4) -0.2096(2) 0.0679(13) Uani 1 1 d . . . . .
H13 H -0.977646 0.129018 -0.182783 0.081 Uiso 1 1 calc R U . . .
C12 C -1.1638(6) 0.0632(6) -0.2195(3) 0.0788(16) Uani 1 1 d . . . . .
H12 H -1.229143 0.114177 -0.199148 0.095 Uiso 1 1 calc R U . . .
C5 C -0.5955(5) -0.1260(4) -0.2950(2) 0.0630(11) Uani 1 1 d . . . . .
H5 H -0.613125 -0.192086 -0.270114 0.076 Uiso 1 1 calc R U . . .
C15 C -0.5537(5) -0.0475(4) -0.1507(2) 0.0601(11) Uani 1 1 d . . . . .
C2 C -0.5410(7) 0.0653(4) -0.3664(2) 0.0741(14) Uani 1 1 d . . . . .
H2 H -0.522513 0.131832 -0.390822 0.089 Uiso 1 1 calc R U . . .
C9 C -0.9719(6) -0.0863(5) -0.2785(3) 0.0741(14) Uani 1 1 d . . . . .
H9 H -0.907609 -0.138033 -0.298924 0.089 Uiso 1 1 calc R U . . .
C24 C -0.8020(5) -0.0295(4) -0.1124(2) 0.0603(11) Uani 1 1 d . . . . .
C19 C -0.9177(6) -0.3363(5) -0.1029(2) 0.0713(13) Uani 1 1 d . . . . .
H19 H -0.898746 -0.406065 -0.124697 0.086 Uiso 1 1 calc R U . . .
C14 C -0.7130(5) -0.0732(4) -0.1672(2) 0.0548(10) Uani 1 1 d . . . . .
C3 C -0.6251(7) 0.0769(4) -0.3160(2) 0.0705(14) Uani 1 1 d . . . . .
H3 H -0.664545 0.151449 -0.306210 0.085 Uiso 1 1 calc R U . . .
C11 C -1.2168(7) -0.0192(7) -0.2592(3) 0.0887(18) Uani 1 1 d . . . . .
H11 H -1.319112 -0.024995 -0.266050 0.106 Uiso 1 1 calc R U . . .
C22 C -0.9760(6) -0.1290(5) -0.0368(2) 0.0719(13) Uani 1 1 d . . . . .
H22 H -0.995154 -0.059543 -0.014790 0.086 Uiso 1 1 calc R U . . .
C10 C -1.1220(7) -0.0933(6) -0.2889(3) 0.0867(17) Uani 1 1 d . . . . .
H10 H -1.159181 -0.149137 -0.316552 0.104 Uiso 1 1 calc R U . . .
C16 C -0.3412(6) -0.1196(6) -0.1021(3) 0.0897(18) Uani 1 1 d . . . . .
H16A H -0.280675 -0.090165 -0.135116 0.135 Uiso 1 1 calc R U . . .
H16B H -0.300335 -0.193471 -0.087271 0.135 Uiso 1 1 calc R U . . .
H16C H -0.342576 -0.062083 -0.069452 0.135 Uiso 1 1 calc R U . . .
C21 C -1.0390(6) -0.2327(6) -0.0209(3) 0.0827(16) Uani 1 1 d . . . . .
H21 H -1.103396 -0.235603 0.012540 0.099 Uiso 1 1 calc R U . . .
C20 C -1.0091(7) -0.3359(6) -0.0537(2) 0.0816(16) Uani 1 1 d . . . . .
O4 O -0.3075(8) -0.2497(5) -0.4766(3) 0.145(2) Uani 1 1 d . . . . .
H4 H -0.274953 -0.309230 -0.458965 0.217 Uiso 1 1 calc R U . . .
C25 C -0.2314(17) -0.2334(9) -0.5307(5) 0.192(6) Uani 1 1 d . . . . .
H25A H -0.229563 -0.307089 -0.553227 0.288 Uiso 1 1 calc R U . . .
H25B H -0.130974 -0.208656 -0.522005 0.288 Uiso 1 1 calc R U . . .
H25C H -0.280456 -0.173131 -0.554660 0.288 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
Cl1 C20 1.744(6) . ?
O2 C15 1.347(6) . ?
O2 C16 1.450(7) . ?
O3 C15 1.203(6) . ?
O5 C24 1.227(6) . ?
O1 H1 0.8400 . ?
O1 C1 1.361(6) . ?
C7 H7 1.0000 . ?
C7 C4 1.532(7) . ?
C7 C8 1.522(7) . ?
C7 C14 1.570(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.503(6) . ?
C17 C14 1.570(6) . ?
C1 C6 1.410(7) . ?
C1 C2 1.383(7) . ?
C4 C5 1.390(6) . ?
C4 C3 1.403(6) . ?
C6 H6 0.9500 . ?
C6 C5 1.387(7) . ?
C23 C18 1.396(6) . ?
C23 C24 1.461(7) . ?
C23 C22 1.401(7) . ?
C18 C19 1.399(7) . ?
C8 C13 1.407(7) . ?
C8 C9 1.391(7) . ?
C13 H13 0.9500 . ?
C13 C12 1.390(7) . ?
C12 H12 0.9500 . ?
C12 C11 1.379(10) . ?
C5 H5 0.9500 . ?
C15 C14 1.530(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.367(8) . ?
C9 H9 0.9500 . ?
C9 C10 1.394(8) . ?
C24 C14 1.548(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.376(8) . ?
C3 H3 0.9500 . ?
C11 H11 0.9500 . ?
C11 C10 1.381(10) . ?
C22 H22 0.9500 . ?
C22 C21 1.364(8) . ?
C10 H10 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C20 1.415(9) . ?
O4 H4 0.8400 . ?
O4 C25 1.403(10) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

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
C15 O2 C16 116.0(4) . . ?
C1 O1 H1 109.5 . . ?
C4 C7 H7 105.6 . . ?
C4 C7 C14 114.4(4) . . ?
C8 C7 H7 105.6 . . ?
C8 C7 C4 113.1(4) . . ?
C8 C7 C14 111.7(4) . . ?
C14 C7 H7 105.6 . . ?
C18 C17 H17 127.2 . . ?
C18 C17 C14 105.6(4) . . ?
C14 C17 H17 127.2 . . ?
O1 C1 C6 122.9(4) . . ?
O1 C1 C2 117.9(4) . . ?
C2 C1 C6 119.1(5) . . ?
C5 C4 C7 125.4(4) . . ?
C5 C4 C3 117.0(4) . . ?
C3 C4 C7 117.6(4) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 C1 118.7(4) . . ?
C5 C6 H6 120.7 . . ?
C18 C23 C24 110.0(4) . . ?
C18 C23 C22 121.2(5) . . ?
C22 C23 C24 128.8(4) . . ?
C23 C18 C17 111.6(4) . . ?
C23 C18 C19 120.8(4) . . ?
C19 C18 C17 127.6(4) . . ?
C13 C8 C7 119.6(5) . . ?
C9 C8 C7 122.5(5) . . ?
C9 C8 C13 117.8(5) . . ?
C8 C13 H13 119.4 . . ?
C12 C13 C8 121.2(6) . . ?
C12 C13 H13 119.4 . . ?
C13 C12 H12 120.2 . . ?
C11 C12 C13 119.6(6) . . ?
C11 C12 H12 120.2 . . ?
C4 C5 H5 118.7 . . ?
C6 C5 C4 122.6(4) . . ?
C6 C5 H5 118.7 . . ?
O2 C15 C14 112.1(4) . . ?
O3 C15 O2 123.3(4) . . ?
O3 C15 C14 124.4(4) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.1(4) . . ?
C3 C2 H2 119.5 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.8(6) . . ?
C10 C9 H9 119.6 . . ?
O5 C24 C23 127.5(5) . . ?
O5 C24 C14 123.5(5) . . ?
C23 C24 C14 109.0(4) . . ?
C18 C19 H19 121.4 . . ?
C20 C19 C18 117.3(5) . . ?
C20 C19 H19 121.4 . . ?
C17 C14 C7 115.4(4) . . ?
C15 C14 C7 107.9(4) . . ?
C15 C14 C17 115.4(4) . . ?
C15 C14 C24 104.5(4) . . ?
C24 C14 C7 109.3(3) . . ?
C24 C14 C17 103.6(4) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 C4 121.5(5) . . ?
C2 C3 H3 119.3 . . ?
C12 C11 H11 119.8 . . ?
C12 C11 C10 120.3(6) . . ?
C10 C11 H11 119.8 . . ?
C23 C22 H22 120.9 . . ?
C21 C22 C23 118.2(5) . . ?
C21 C22 H22 120.9 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.2(6) . . ?
C11 C10 H10 119.9 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C21 H21 119.7 . . ?
C22 C21 C20 120.5(5) . . ?
C20 C21 H21 119.7 . . ?
C19 C20 Cl1 118.9(5) . . ?
C19 C20 C21 122.0(5) . . ?
C21 C20 Cl1 119.1(4) . . ?
C25 O4 H4 109.5 . . ?
O4 C25 H25A 109.5 . . ?
O4 C25 H25B 109.5 . . ?
O4 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C15 C14 C7 -151.7(4) . . . . ?
O2 C15 C14 C17 -21.0(6) . . . . ?
O2 C15 C14 C24 92.0(4) . . . . ?
O3 C15 C14 C7 32.9(7) . . . . ?
O3 C15 C14 C17 163.6(5) . . . . ?
O3 C15 C14 C24 -83.3(6) . . . . ?
O5 C24 C14 C7 -55.1(6) . . . . ?
O5 C24 C14 C17 -178.7(5) . . . . ?
O5 C24 C14 C15 60.2(6) . . . . ?
O1 C1 C6 C5 178.0(5) . . . . ?
O1 C1 C2 C3 -179.1(5) . . . . ?
C7 C4 C5 C6 177.2(4) . . . . ?
C7 C4 C3 C2 -178.5(5) . . . . ?
C7 C8 C13 C12 -176.6(5) . . . . ?
C7 C8 C9 C10 177.4(5) . . . . ?
C17 C18 C19 C20 -178.4(5) . . . . ?
C1 C6 C5 C4 1.7(7) . . . . ?
C1 C2 C3 C4 0.5(9) . . . . ?
C4 C7 C8 C13 -143.5(4) . . . . ?
C4 C7 C8 C9 38.4(6) . . . . ?
C4 C7 C14 C17 -73.1(5) . . . . ?
C4 C7 C14 C15 57.5(5) . . . . ?
C4 C7 C14 C24 170.6(4) . . . . ?
C6 C1 C2 C3 0.8(8) . . . . ?
C23 C18 C19 C20 0.3(7) . . . . ?
C23 C24 C14 C7 125.2(4) . . . . ?
C23 C24 C14 C17 1.7(5) . . . . ?
C23 C24 C14 C15 -119.5(4) . . . . ?
C23 C22 C21 C20 0.4(8) . . . . ?
C18 C17 C14 C7 -122.0(4) . . . . ?
C18 C17 C14 C15 111.0(4) . . . . ?
C18 C17 C14 C24 -2.5(5) . . . . ?
C18 C23 C24 O5 -179.7(5) . . . . ?
C18 C23 C24 C14 -0.1(5) . . . . ?
C18 C23 C22 C21 0.1(8) . . . . ?
C18 C19 C20 Cl1 -179.6(4) . . . . ?
C18 C19 C20 C21 0.3(9) . . . . ?
C8 C7 C4 C5 -93.5(5) . . . . ?
C8 C7 C4 C3 84.2(5) . . . . ?
C8 C7 C14 C17 57.0(5) . . . . ?
C8 C7 C14 C15 -172.3(4) . . . . ?
C8 C7 C14 C24 -59.3(5) . . . . ?
C8 C13 C12 C11 -1.1(8) . . . . ?
C8 C9 C10 C11 -0.4(9) . . . . ?
C13 C8 C9 C10 -0.8(8) . . . . ?
C13 C12 C11 C10 -0.1(9) . . . . ?
C12 C11 C10 C9 0.8(9) . . . . ?
C5 C4 C3 C2 -0.7(8) . . . . ?
C2 C1 C6 C5 -1.8(7) . . . . ?
C9 C8 C13 C12 1.5(7) . . . . ?
C24 C23 C18 C17 -1.7(5) . . . . ?
C24 C23 C18 C19 179.4(4) . . . . ?
C24 C23 C22 C21 -179.8(5) . . . . ?
C14 C7 C4 C5 35.9(6) . . . . ?
C14 C7 C4 C3 -146.4(4) . . . . ?
C14 C7 C8 C13 85.8(5) . . . . ?
C14 C7 C8 C9 -92.3(6) . . . . ?
C14 C17 C18 C23 2.7(5) . . . . ?
C14 C17 C18 C19 -178.5(5) . . . . ?
C3 C4 C5 C6 -0.4(7) . . . . ?
C22 C23 C18 C17 178.4(4) . . . . ?
C22 C23 C18 C19 -0.5(7) . . . . ?
C22 C23 C24 O5 0.1(9) . . . . ?
C22 C23 C24 C14 179.8(5) . . . . ?
C22 C21 C20 Cl1 179.2(5) . . . . ?
C22 C21 C20 C19 -0.6(9) . . . . ?
C16 O2 C15 O3 -0.1(8) . . . . ?
C16 O2 C15 C14 -175.5(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
