# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_zz
_database_code_depnum_ccdc_archive 'CCDC 2253406'
loop_
_audit_author_name
_audit_author_address
'Zaiyong Zhang'
;Shanghai Institute of Materia Medica, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-04-02 deposited with the CCDC.	2025-03-06 downloaded from the CCDC.
;
_audit_creation_date             2022-11-24
_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         'C16 H10 F3 N O3'
_chemical_formula_sum            'C16 H10 F3 N O3'
_chemical_formula_weight         321.25
_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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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                   12.132(3)
_cell_length_b                   13.549(3)
_cell_length_c                   8.342(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.244(9)
_cell_angle_gamma                90
_cell_volume                     1356.9(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1311
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.928
_cell_measurement_theta_min      2.267
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.8562
_exptl_absorpt_correction_T_min  0.5623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 16149 reflections, Rint = 0.1066
 (6397 with I > 3sig(I), Rint = 0.0794)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.1143
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            2745
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.350
_diffrn_reflns_theta_min         2.266
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'D8 VENTURE'
_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                1737
_reflns_number_total             2745
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 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         0.388
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2745
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1509
_refine_ls_R_factor_gt           0.0877
_refine_ls_restrained_S_all      1.089
_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)+(0.0777P)²+2.1903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1842
_refine_ls_wR_factor_ref         0.2128
_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:
 C6(H6), C13(H13), C8(H8), C11(H11), C3(H3), C12(H12), C9(H9)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_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
F1 F 0.0036(2) 0.4482(2) 0.2464(3) 0.0434(7) Uani 1 1 d . . . . .
F3 F 0.1189(2) 0.5219(2) 0.1159(3) 0.0487(8) Uani 1 1 d . . . . .
F2 F 0.1510(2) 0.3735(2) 0.1986(3) 0.0531(9) Uani 1 1 d . . . . .
O1 O 0.6227(2) 0.6226(2) 0.9414(3) 0.0300(7) Uani 1 1 d . . . . .
O2 O 0.3574(2) 0.6281(2) 1.1949(3) 0.0347(8) Uani 1 1 d . . . . .
O3 O 0.2551(2) 0.4469(2) 0.4631(3) 0.0343(8) Uani 1 1 d . . . . .
N1 N 0.1998(3) 0.6423(3) 0.5862(4) 0.0238(8) Uani 1 1 d . . . . .
C5 C 0.4226(3) 0.6243(3) 0.9396(5) 0.0227(9) Uani 1 1 d . . . . .
C15 C 0.1784(3) 0.4979(3) 0.3986(5) 0.0260(9) Uani 1 1 d . . . . .
C7 C 0.3077(3) 0.6247(3) 0.6789(4) 0.0212(9) Uani 1 1 d . . . . .
C10 C 0.5161(3) 0.6194(3) 0.8600(5) 0.0247(9) Uani 1 1 d . . . . .
C14 C 0.1423(3) 0.5905(3) 0.4556(5) 0.0246(9) Uani 1 1 d . . . . .
C6 C 0.3173(3) 0.6265(3) 0.8454(5) 0.0241(9) Uani 1 1 d . . . . .
H6 H 0.252260 0.629149 0.896567 0.029 Uiso 1 1 calc R . . . .
C13 C 0.0459(3) 0.6439(3) 0.4051(5) 0.0303(10) Uani 1 1 d . . . . .
H13 H -0.010100 0.626147 0.318313 0.036 Uiso 1 1 calc R . . . .
C8 C 0.4019(3) 0.6160(3) 0.6011(5) 0.0255(9) Uani 1 1 d . . . . .
H8 H 0.393948 0.612116 0.486291 0.031 Uiso 1 1 calc R . . . .
C11 C 0.1408(3) 0.7246(3) 0.6117(5) 0.0287(10) Uani 1 1 d . . . . .
H11 H 0.162353 0.772928 0.692723 0.034 Uiso 1 1 calc R . . . .
C1 C 0.6371(3) 0.6320(3) 1.1070(5) 0.0290(10) Uani 1 1 d . . . . .
C4 C 0.4375(3) 0.6283(3) 1.1181(5) 0.0277(10) Uani 1 1 d . . . . .
C3 C 0.5519(3) 0.6339(3) 1.1927(5) 0.0282(10) Uani 1 1 d . . . . .
H3 H 0.567561 0.639086 1.307263 0.034 Uiso 1 1 calc R . . . .
C12 C 0.0442(3) 0.7270(4) 0.5010(5) 0.0337(11) Uani 1 1 d . . . . .
H12 H -0.012302 0.776056 0.492619 0.040 Uiso 1 1 calc R . . . .
C9 C 0.5060(3) 0.6129(3) 0.6909(5) 0.0258(9) Uani 1 1 d . . . . .
H9 H 0.570343 0.606553 0.638937 0.031 Uiso 1 1 calc R . . . .
C16 C 0.1126(3) 0.4598(3) 0.2392(5) 0.0314(10) Uani 1 1 d . . . . .
C2 C 0.7588(4) 0.6411(4) 1.1709(5) 0.0413(12) Uani 1 1 d . . . . .
H2A H 0.798572 0.583427 1.137653 0.062 Uiso 1 1 calc GR . . . .
H2B H 0.768537 0.644859 1.289442 0.062 Uiso 1 1 calc GR . . . .
H2C H 0.788599 0.701107 1.127417 0.062 Uiso 1 1 calc GR . . . .


_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
F1 C16 1.342(5) . ?
F3 C16 1.340(5) . ?
F2 C16 1.320(5) . ?
O1 C10 1.372(5) . ?
O1 C1 1.374(5) . ?
O2 C4 1.238(5) . ?
O3 C15 1.221(5) . ?
N1 C7 1.441(5) . ?
N1 C14 1.396(5) . ?
N1 C11 1.359(5) . ?
C5 C10 1.396(6) . ?
C5 C6 1.401(5) . ?
C5 C4 1.475(5) . ?
C15 C14 1.432(6) . ?
C15 C16 1.539(6) . ?
C7 C6 1.377(5) . ?
C7 C8 1.399(5) . ?
C10 C9 1.401(6) . ?
C14 C13 1.389(6) . ?
C6 H6 0.9500 . ?
C13 H13 0.9500 . ?
C13 C12 1.383(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.373(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(6) . ?
C1 C3 1.339(6) . ?
C1 C2 1.500(6) . ?
C4 C3 1.440(6) . ?
C3 H3 0.9500 . ?
C12 H12 0.9500 . ?
C9 H9 0.9500 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 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
C10 O1 C1 118.4(3) . . ?
C14 N1 C7 130.5(3) . . ?
C11 N1 C7 120.7(3) . . ?
C11 N1 C14 108.6(3) . . ?
C10 C5 C6 118.2(3) . . ?
C10 C5 C4 119.5(3) . . ?
C6 C5 C4 122.3(3) . . ?
O3 C15 C14 126.9(4) . . ?
O3 C15 C16 117.3(4) . . ?
C14 C15 C16 115.8(3) . . ?
C6 C7 N1 118.5(3) . . ?
C6 C7 C8 120.9(3) . . ?
C8 C7 N1 120.3(3) . . ?
O1 C10 C5 122.4(3) . . ?
O1 C10 C9 116.2(3) . . ?
C5 C10 C9 121.5(4) . . ?
N1 C14 C15 123.8(3) . . ?
C13 C14 N1 106.3(4) . . ?
C13 C14 C15 129.8(4) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.3(4) . . ?
C7 C6 H6 119.9 . . ?
C14 C13 H13 125.3 . . ?
C12 C13 C14 109.3(4) . . ?
C12 C13 H13 125.3 . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.9(4) . . ?
C9 C8 H8 120.1 . . ?
N1 C11 H11 125.4 . . ?
N1 C11 C12 109.2(4) . . ?
C12 C11 H11 125.4 . . ?
O1 C1 C2 110.0(4) . . ?
C3 C1 O1 122.8(4) . . ?
C3 C1 C2 127.2(4) . . ?
O2 C4 C5 122.1(4) . . ?
O2 C4 C3 123.8(4) . . ?
C3 C4 C5 114.1(4) . . ?
C1 C3 C4 122.6(4) . . ?
C1 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
C13 C12 C11 106.6(4) . . ?
C13 C12 H12 126.7 . . ?
C11 C12 H12 126.7 . . ?
C10 C9 H9 120.4 . . ?
C8 C9 C10 119.3(4) . . ?
C8 C9 H9 120.4 . . ?
F1 C16 C15 113.1(3) . . ?
F3 C16 F1 105.8(3) . . ?
F3 C16 C15 111.9(3) . . ?
F2 C16 F1 107.1(3) . . ?
F2 C16 F3 107.4(4) . . ?
F2 C16 C15 111.1(3) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?


_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_cu_20231315_0m
_database_code_depnum_ccdc_archive 'CCDC 2371783'
loop_
_audit_author_name
_audit_author_address
'Zaiyong Zhang'
;Shanghai Institute of Materia Medica, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2024-07-18 deposited with the CCDC.	2025-03-06 downloaded from the CCDC.
;
_audit_creation_date             2023-08-24
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 Br2 O4'
_chemical_formula_sum            'C18 H16 Br2 O4'
_chemical_formula_weight         456.13
_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'
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                   9.4779(6)
_cell_length_b                   17.4082(10)
_cell_length_c                   10.9215(7)
_cell_angle_alpha                90
_cell_angle_beta                 111.049(3)
_cell_angle_gamma                90
_cell_volume                     1681.73(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8432
_cell_measurement_temperature    100
_cell_measurement_theta_max      64.111
_cell_measurement_theta_min      2.538
_shelx_estimated_absorpt_T_max   0.744
_shelx_estimated_absorpt_T_min   0.381
_exptl_absorpt_coefficient_mu    6.290
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.1984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1717 before and 0.0965 after correction.
The Ratio of minimum to maximum transmission is 0.2637.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.802
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11656
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        64.119
_diffrn_reflns_theta_max         64.119
_diffrn_reflns_theta_min         5.028
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2606
_reflns_number_total             2750
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         2.114
_refine_diff_density_min         -1.289
_refine_diff_density_rms         0.281
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2750
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0903
_refine_ls_restrained_S_all      1.096
_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)+(0.1881P)²+2.4289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2426
_refine_ls_wR_factor_ref         0.2467
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C15(H15)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C10(H10A,H10B,H10C), C17(H17A,H17B,H17C)
;
_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 -0.09346(8) 0.65169(4) 0.14220(7) 0.0470(4) Uani 1 1 d . . . . .
Br2 Br 0.04110(9) 0.33343(4) 0.18980(7) 0.0470(4) Uani 1 1 d . . . . .
O1 O 0.2300(6) 0.6619(3) 0.1631(5) 0.0452(12) Uani 1 1 d . . . . .
O3 O 0.5046(5) 0.3896(3) 0.0867(4) 0.0451(11) Uani 1 1 d . . . . .
O4 O 0.7934(5) 0.4678(3) 0.4374(4) 0.0467(11) Uani 1 1 d . . . . .
O2 O 0.6865(5) 0.5790(3) 0.4204(5) 0.0484(12) Uani 1 1 d . . . . .
C2 C 0.0448(8) 0.5700(4) 0.1586(6) 0.0436(15) Uani 1 1 d . . . . .
C4 C 0.0990(8) 0.4360(4) 0.1781(6) 0.0412(14) Uani 1 1 d . . . . .
C3 C -0.0016(8) 0.4954(4) 0.1673(6) 0.0422(14) Uani 1 1 d . . . . .
H3 H -0.100705 0.485278 0.165770 0.051 Uiso 1 1 calc R U . . .
C18 C 0.1892(8) 0.5867(4) 0.1626(6) 0.0408(14) Uani 1 1 d . . . . .
C5 C 0.2415(8) 0.4501(4) 0.1783(6) 0.0424(15) Uani 1 1 d . . . . .
H5 H 0.307837 0.408274 0.183223 0.051 Uiso 1 1 calc R U . . .
C7 C 0.4489(8) 0.5419(4) 0.1717(6) 0.0435(15) Uani 1 1 d . . . . .
H7 H 0.442706 0.537545 0.078633 0.052 Uiso 1 1 calc R U . . .
C14 C 0.5904(8) 0.4135(4) 0.1962(6) 0.0415(14) Uani 1 1 d . . . . .
C16 C 0.8100(8) 0.3955(4) 0.3943(7) 0.0446(15) Uani 1 1 d . . . . .
C12 C 0.5695(8) 0.4864(4) 0.2501(6) 0.0425(15) Uani 1 1 d . . . . .
C6 C 0.2906(7) 0.5254(4) 0.1714(6) 0.0389(14) Uani 1 1 d . . . . .
C15 C 0.7183(8) 0.3686(4) 0.2801(7) 0.0427(14) Uani 1 1 d . . . . .
H15 H 0.736226 0.319055 0.252230 0.051 Uiso 1 1 calc R U . . .
C13 C 0.6746(8) 0.5106(4) 0.3627(6) 0.0412(14) Uani 1 1 d . . . . .
C9 C 0.5609(8) 0.6344(4) 0.3654(7) 0.0467(16) Uani 1 1 d . . . . .
C11 C 0.6374(9) 0.7113(4) 0.4068(8) 0.0543(18) Uani 1 1 d . . . . .
H11A H 0.688739 0.712152 0.502303 0.081 Uiso 1 1 calc R U . . .
H11B H 0.561398 0.752236 0.380440 0.081 Uiso 1 1 calc R U . . .
H11C H 0.711525 0.719332 0.364492 0.081 Uiso 1 1 calc R U . . .
C8 C 0.4968(8) 0.6243(4) 0.2145(7) 0.0442(15) Uani 1 1 d . . . . .
H8 H 0.581113 0.636733 0.183022 0.053 Uiso 1 1 calc R U . . .
C1 C 0.3665(8) 0.6770(4) 0.1407(7) 0.0456(16) Uani 1 1 d . . . . .
H1A H 0.397338 0.730751 0.166465 0.055 Uiso 1 1 calc R U . . .
H1B H 0.346373 0.672291 0.045624 0.055 Uiso 1 1 calc R U . . .
C10 C 0.4540(8) 0.6174(5) 0.4379(7) 0.0500(17) Uani 1 1 d . . . . .
H10A H 0.415588 0.564850 0.418509 0.075 Uiso 1 1 calc R U . . .
H10B H 0.369231 0.653646 0.409455 0.075 Uiso 1 1 calc R U . . .
H10C H 0.508483 0.622923 0.532566 0.075 Uiso 1 1 calc R U . . .
C17 C 0.9454(9) 0.3549(5) 0.4895(7) 0.0499(18) Uani 1 1 d . . . . .
H17A H 1.037953 0.380945 0.491798 0.075 Uiso 1 1 calc R U . . .
H17B H 0.946828 0.301538 0.461292 0.075 Uiso 1 1 calc R U . . .
H17C H 0.939378 0.355727 0.577183 0.075 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
Br1 C2 1.898(7) . ?
Br2 C4 1.885(6) . ?
O1 C18 1.364(8) . ?
O1 C1 1.425(9) . ?
O3 C14 1.252(8) . ?
O4 C16 1.371(8) . ?
O4 C13 1.353(8) . ?
O2 C13 1.334(8) . ?
O2 C9 1.481(8) . ?
C2 C3 1.385(10) . ?
C2 C18 1.385(10) . ?
C4 C3 1.383(10) . ?
C4 C5 1.373(10) . ?
C3 H3 0.9500 . ?
C18 C6 1.415(9) . ?
C5 H5 0.9500 . ?
C5 C6 1.402(9) . ?
C7 H7 1.0000 . ?
C7 C12 1.506(9) . ?
C7 C6 1.527(10) . ?
C7 C8 1.526(9) . ?
C14 C12 1.441(10) . ?
C14 C15 1.457(9) . ?
C16 C15 1.324(10) . ?
C16 C17 1.506(9) . ?
C12 C13 1.342(9) . ?
C15 H15 0.9500 . ?
C9 C11 1.513(10) . ?
C9 C8 1.548(10) . ?
C9 C10 1.522(11) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C8 H8 1.0000 . ?
C8 C1 1.517(10) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C18 O1 C1 116.8(5) . . ?
C13 O4 C16 118.1(5) . . ?
C13 O2 C9 118.1(5) . . ?
C3 C2 Br1 118.9(5) . . ?
C3 C2 C18 121.9(6) . . ?
C18 C2 Br1 119.2(5) . . ?
C3 C4 Br2 120.4(5) . . ?
C5 C4 Br2 118.7(5) . . ?
C5 C4 C3 120.9(6) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.8(7) . . ?
C4 C3 H3 120.6 . . ?
O1 C18 C2 118.4(6) . . ?
O1 C18 C6 122.6(6) . . ?
C2 C18 C6 118.9(6) . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(6) . . ?
C6 C5 H5 119.6 . . ?
C12 C7 H7 106.5 . . ?
C12 C7 C6 115.1(5) . . ?
C12 C7 C8 110.3(6) . . ?
C6 C7 H7 106.5 . . ?
C8 C7 H7 106.5 . . ?
C8 C7 C6 111.2(6) . . ?
O3 C14 C12 123.1(6) . . ?
O3 C14 C15 122.0(6) . . ?
C12 C14 C15 114.9(6) . . ?
O4 C16 C17 111.6(6) . . ?
C15 C16 O4 122.1(6) . . ?
C15 C16 C17 126.3(7) . . ?
C14 C12 C7 121.3(6) . . ?
C13 C12 C7 118.7(6) . . ?
C13 C12 C14 119.0(6) . . ?
C18 C6 C7 120.1(6) . . ?
C5 C6 C18 118.6(6) . . ?
C5 C6 C7 121.4(6) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.2(6) . . ?
C16 C15 H15 119.4 . . ?
O2 C13 O4 107.2(5) . . ?
O2 C13 C12 128.5(6) . . ?
C12 C13 O4 124.3(6) . . ?
O2 C9 C11 103.0(6) . . ?
O2 C9 C8 108.0(6) . . ?
O2 C9 C10 104.6(6) . . ?
C11 C9 C8 112.4(6) . . ?
C11 C9 C10 110.7(6) . . ?
C10 C9 C8 116.9(6) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C8 C9 113.1(6) . . ?
C7 C8 H8 106.6 . . ?
C9 C8 H8 106.6 . . ?
C1 C8 C7 108.1(6) . . ?
C1 C8 C9 115.4(6) . . ?
C1 C8 H8 106.6 . . ?
O1 C1 C8 114.4(6) . . ?
O1 C1 H1A 108.7 . . ?
O1 C1 H1B 108.7 . . ?
C8 C1 H1A 108.7 . . ?
C8 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
Br1 C2 C3 C4 179.4(5) . . . . ?
Br1 C2 C18 O1 4.2(8) . . . . ?
Br1 C2 C18 C6 -178.4(5) . . . . ?
Br2 C4 C3 C2 -179.9(5) . . . . ?
Br2 C4 C5 C6 -179.2(5) . . . . ?
O1 C18 C6 C5 176.1(6) . . . . ?
O1 C18 C6 C7 -4.6(9) . . . . ?
O3 C14 C12 C7 -5.2(11) . . . . ?
O3 C14 C12 C13 -174.0(7) . . . . ?
O3 C14 C15 C16 178.4(7) . . . . ?
O4 C16 C15 C14 -2.6(11) . . . . ?
O2 C9 C8 C7 55.1(8) . . . . ?
O2 C9 C8 C1 -179.7(6) . . . . ?
C2 C18 C6 C5 -1.2(9) . . . . ?
C2 C18 C6 C7 178.1(6) . . . . ?
C4 C5 C6 C18 -0.7(9) . . . . ?
C4 C5 C6 C7 180.0(6) . . . . ?
C3 C2 C18 O1 -175.3(6) . . . . ?
C3 C2 C18 C6 2.1(10) . . . . ?
C3 C4 C5 C6 1.8(10) . . . . ?
C18 O1 C1 C8 -43.6(8) . . . . ?
C18 C2 C3 C4 -1.0(10) . . . . ?
C5 C4 C3 C2 -1.0(10) . . . . ?
C7 C12 C13 O4 -175.8(6) . . . . ?
C7 C12 C13 O2 2.2(11) . . . . ?
C7 C8 C1 O1 59.6(8) . . . . ?
C14 C12 C13 O4 -6.8(11) . . . . ?
C14 C12 C13 O2 171.3(7) . . . . ?
C16 O4 C13 O2 -176.9(6) . . . . ?
C16 O4 C13 C12 1.5(10) . . . . ?
C12 C7 C6 C18 148.4(6) . . . . ?
C12 C7 C6 C5 -32.3(9) . . . . ?
C12 C7 C8 C9 -46.4(8) . . . . ?
C12 C7 C8 C1 -175.4(6) . . . . ?
C12 C14 C15 C16 -2.5(10) . . . . ?
C6 C7 C12 C14 81.9(8) . . . . ?
C6 C7 C12 C13 -109.3(7) . . . . ?
C6 C7 C8 C9 82.7(7) . . . . ?
C6 C7 C8 C1 -46.4(7) . . . . ?
C15 C14 C12 C7 175.7(6) . . . . ?
C15 C14 C12 C13 7.0(10) . . . . ?
C13 O4 C16 C15 3.4(10) . . . . ?
C13 O4 C16 C17 -178.8(6) . . . . ?
C13 O2 C9 C11 -154.6(6) . . . . ?
C13 O2 C9 C8 -35.5(8) . . . . ?
C13 O2 C9 C10 89.7(7) . . . . ?
C9 O2 C13 O4 -173.7(6) . . . . ?
C9 O2 C13 C12 8.0(11) . . . . ?
C9 C8 C1 O1 -68.1(8) . . . . ?
C11 C9 C8 C7 168.1(6) . . . . ?
C11 C9 C8 C1 -66.8(8) . . . . ?
C8 C7 C12 C14 -151.2(7) . . . . ?
C8 C7 C12 C13 17.6(9) . . . . ?
C8 C7 C6 C18 21.9(8) . . . . ?
C8 C7 C6 C5 -158.8(6) . . . . ?
C1 O1 C18 C2 -167.8(6) . . . . ?
C1 O1 C18 C6 14.9(9) . . . . ?
C10 C9 C8 C7 -62.4(8) . . . . ?
C10 C9 C8 C1 62.8(8) . . . . ?
C17 C16 C15 C14 179.9(7) . . . . ?

_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_cu_2023724_0m
_database_code_depnum_ccdc_archive 'CCDC 2371778'
loop_
_audit_author_name
_audit_author_address
'Zaiyong Zhang'
;Shanghai Institute of Materia Medica, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2024-07-18 deposited with the CCDC.	2025-03-06 downloaded from the CCDC.
;
_audit_creation_date             2023-05-05
_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         'C16 H22 O3'
_chemical_formula_sum            'C16 H22 O3'
_chemical_formula_weight         262.33
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5339(4)
_cell_length_b                   9.6176(4)
_cell_length_c                   9.7437(4)
_cell_angle_alpha                62.587(2)
_cell_angle_beta                 72.018(2)
_cell_angle_gamma                65.461(2)
_cell_volume                     713.80(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3898
_cell_measurement_temperature    170
_cell_measurement_theta_max      74.235
_cell_measurement_theta_min      5.155
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.901
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1291 before and 0.0821 after correction. The Ratio of minimum to maximum transmission is 0.6733. 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    1.221
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6806
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.226
_diffrn_reflns_theta_min         5.155
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1998
_reflns_number_total             2561
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 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         0.301
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2561
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0645
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1181P)²+0.0530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1799
_refine_ls_wR_factor_ref         0.1996
_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
2.a Ternary CH refined with riding coordinates:
 C6(H6), C5(H5), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C12(H12A,H12B,H12C), C16(H16A,H16B,
 H16C)
;
_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
O2 O 0.21528(15) 0.36991(16) 0.54580(17) 0.0321(4) Uani 1 1 d . . . . .
O3 O 0.27690(14) 0.48852(15) 0.65021(16) 0.0307(4) Uani 1 1 d . . . . .
O1 O 0.48962(17) -0.09228(16) 0.77888(17) 0.0371(4) Uani 1 1 d . . . . .
C7 C 0.4127(2) 0.1964(2) 0.7140(2) 0.0278(4) Uani 1 1 d . . . . .
C8 C 0.3080(2) 0.3431(2) 0.6429(2) 0.0275(4) Uani 1 1 d . . . . .
C9 C 0.4140(2) 0.0505(2) 0.7026(2) 0.0294(4) Uani 1 1 d . . . . .
C6 C 0.5214(2) 0.1909(2) 0.8029(2) 0.0288(4) Uani 1 1 d . . . . .
H6 H 0.484627 0.142807 0.917445 0.035 Uiso 1 1 calc R . . . .
C5 C 0.5165(2) 0.3677(2) 0.7588(2) 0.0287(4) Uani 1 1 d . . . . .
H5 H 0.564528 0.407628 0.646775 0.034 Uiso 1 1 calc R . . . .
C10 C 0.3203(2) 0.0859(2) 0.5894(2) 0.0321(5) Uani 1 1 d . . . . .
H10 H 0.325385 -0.002623 0.567152 0.038 Uiso 1 1 calc R . . . .
C13 C 0.3480(2) 0.4841(2) 0.7682(2) 0.0303(5) Uani 1 1 d . . . . .
C11 C 0.2284(2) 0.2373(2) 0.5165(2) 0.0320(5) Uani 1 1 d . . . . .
C2 C 0.7984(2) 0.0844(3) 0.8581(2) 0.0362(5) Uani 1 1 d . . . . .
H2 H 0.763884 0.031342 0.972482 0.043 Uiso 1 1 calc R . . . .
C1 C 0.6904(2) 0.0865(2) 0.7682(2) 0.0333(5) Uani 1 1 d . . . . .
H1A H 0.694860 -0.028288 0.797481 0.040 Uiso 1 1 calc R . . . .
H1B H 0.727153 0.132127 0.654663 0.040 Uiso 1 1 calc R . . . .
C15 C 0.3389(2) 0.6631(2) 0.7120(3) 0.0366(5) Uani 1 1 d . . . . .
H15A H 0.411669 0.690909 0.615205 0.055 Uiso 1 1 calc GR . . . .
H15B H 0.366558 0.677928 0.792130 0.055 Uiso 1 1 calc GR . . . .
H15C H 0.232608 0.735846 0.692461 0.055 Uiso 1 1 calc GR . . . .
C3 C 0.7868(3) 0.2611(3) 0.8218(3) 0.0405(5) Uani 1 1 d . . . . .
H3A H 0.829234 0.312065 0.710796 0.049 Uiso 1 1 calc R . . . .
H3B H 0.850838 0.257816 0.886914 0.049 Uiso 1 1 calc R . . . .
C14 C 0.2488(3) 0.4285(3) 0.9266(3) 0.0411(5) Uani 1 1 d . . . . .
H14A H 0.146089 0.513301 0.926435 0.062 Uiso 1 1 calc GR . . . .
H14B H 0.300009 0.412118 1.008464 0.062 Uiso 1 1 calc GR . . . .
H14C H 0.236412 0.324172 0.946882 0.062 Uiso 1 1 calc GR . . . .
C4 C 0.6181(2) 0.3678(3) 0.8533(2) 0.0363(5) Uani 1 1 d . . . . .
H4A H 0.578175 0.323383 0.966083 0.044 Uiso 1 1 calc R . . . .
H4B H 0.614021 0.482528 0.823568 0.044 Uiso 1 1 calc R . . . .
C12 C 0.1290(3) 0.2915(3) 0.3979(3) 0.0413(5) Uani 1 1 d . . . . .
H12A H 0.020426 0.344425 0.434738 0.062 Uiso 1 1 calc GR . . . .
H12B H 0.136425 0.195039 0.381963 0.062 Uiso 1 1 calc GR . . . .
H12C H 0.164660 0.370521 0.299012 0.062 Uiso 1 1 calc GR . . . .
C16 C 0.9649(3) -0.0192(3) 0.8185(3) 0.0482(6) Uani 1 1 d . . . . .
H16A H 0.970060 -0.134417 0.854606 0.072 Uiso 1 1 calc GR . . . .
H16B H 1.034792 -0.013942 0.870234 0.072 Uiso 1 1 calc GR . . . .
H16C H 0.996777 0.024177 0.705105 0.072 Uiso 1 1 calc GR . . . .


_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
O2 C8 1.359(2) . ?
O2 C11 1.380(2) . ?
O3 C8 1.335(2) . ?
O3 C13 1.482(2) . ?
O1 C9 1.235(2) . ?
C7 C8 1.351(3) . ?
C7 C9 1.453(3) . ?
C7 C6 1.515(2) . ?
C9 C10 1.463(3) . ?
C6 H6 1.0000 . ?
C6 C5 1.533(3) . ?
C6 C1 1.533(3) . ?
C5 H5 1.0000 . ?
C5 C13 1.534(3) . ?
C5 C4 1.529(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.329(3) . ?
C13 C15 1.519(3) . ?
C13 C14 1.524(3) . ?
C11 C12 1.489(3) . ?
C2 H2 1.0000 . ?
C2 C1 1.533(3) . ?
C2 C3 1.530(3) . ?
C2 C16 1.524(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.532(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C8 O2 C11 117.85(14) . . ?
C8 O3 C13 116.05(13) . . ?
C8 C7 C9 117.94(16) . . ?
C8 C7 C6 118.91(16) . . ?
C9 C7 C6 123.15(16) . . ?
O3 C8 O2 106.78(14) . . ?
O3 C8 C7 127.91(16) . . ?
C7 C8 O2 125.29(16) . . ?
O1 C9 C7 123.63(17) . . ?
O1 C9 C10 121.94(16) . . ?
C7 C9 C10 114.41(16) . . ?
C7 C6 H6 108.8 . . ?
C7 C6 C5 109.11(15) . . ?
C7 C6 C1 112.57(14) . . ?
C5 C6 H6 108.8 . . ?
C5 C6 C1 108.76(16) . . ?
C1 C6 H6 108.8 . . ?
C6 C5 H5 106.7 . . ?
C6 C5 C13 111.07(16) . . ?
C13 C5 H5 106.7 . . ?
C4 C5 C6 110.53(15) . . ?
C4 C5 H5 106.7 . . ?
C4 C5 C13 114.60(15) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 C9 122.35(16) . . ?
C11 C10 H10 118.8 . . ?
O3 C13 C5 106.57(13) . . ?
O3 C13 C15 102.87(15) . . ?
O3 C13 C14 107.95(16) . . ?
C15 C13 C5 112.38(17) . . ?
C15 C13 C14 111.92(16) . . ?
C14 C13 C5 114.25(17) . . ?
O2 C11 C12 110.68(17) . . ?
C10 C11 O2 121.20(16) . . ?
C10 C11 C12 128.12(18) . . ?
C1 C2 H2 108.3 . . ?
C3 C2 H2 108.3 . . ?
C3 C2 C1 110.39(16) . . ?
C16 C2 H2 108.3 . . ?
C16 C2 C1 109.61(16) . . ?
C16 C2 C3 111.79(19) . . ?
C6 C1 H1A 109.3 . . ?
C6 C1 H1B 109.3 . . ?
C2 C1 C6 111.58(15) . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C2 C3 C4 111.73(18) . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C4 C3 109.80(15) . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C16 H16A 109.5 . . ?
C2 C16 H16B 109.5 . . ?
C2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
