# Electronic Supplementary Material (ESI) for Organic 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_437-1
_database_code_depnum_ccdc_archive 'CCDC 2150312'
loop_
_audit_author_name
_audit_author_address
'Rao Weidong'
;Nanjing Forestry University
China
;
_audit_update_record             
;
2022-02-06 deposited with the CCDC.	2022-05-22 downloaded from the CCDC.
;
_audit_creation_date             2021-09-09
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H22 O4'
_chemical_formula_sum            'C21 H22 O4'
_chemical_formula_weight         338.38
_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'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.9944(14)
_cell_length_b                   8.3336(7)
_cell_length_c                   26.5724(19)
_cell_angle_alpha                90
_cell_angle_beta                 94.331(8)
_cell_angle_gamma                90
_cell_volume                     3531.8(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3875
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      28.4010
_cell_measurement_theta_min      2.7350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            11830
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.554
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  78.00   1.00    2.00    --   11.90  37.00  60.00   90
  2  ω     38.00  63.00   1.00    2.00    --  -11.27  37.00-120.00   25
  3  ω    -15.00  30.00   1.00    2.00    --  -11.27 -99.00  30.00   45
  4  ω    -64.00  43.00   1.00    2.00    --   11.90 -77.00 -90.00  107
  5  ω      5.00  62.00   1.00    2.00    --   11.90  37.00-180.00   57
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0265264500
_diffrn_orient_matrix_UB_12      -0.0510767500
_diffrn_orient_matrix_UB_13      0.0154665000
_diffrn_orient_matrix_UB_21      -0.0357022500
_diffrn_orient_matrix_UB_22      -0.0382145500
_diffrn_orient_matrix_UB_23      0.0088278000
_diffrn_orient_matrix_UB_31      0.0002286000
_diffrn_orient_matrix_UB_32      -0.0563489000
_diffrn_orient_matrix_UB_33      -0.0199826000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2460
_reflns_number_total             3075
_reflns_odcompleteness_completeness 97.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0035(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3075
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0501
_refine_ls_restrained_S_all      1.080
_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)+(0.0539P)²+1.8446P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1302
_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:
 C2(H2), C3(H3), C16(H16), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.40966(9) 0.14593(18) 0.49417(5) 0.0432(4) Uani 1 1 d . . . . .
O2 O 0.37262(8) 0.15475(19) 0.68931(5) 0.0431(4) Uani 1 1 d . . . . .
O3 O 0.18035(8) 0.17914(18) 0.66342(5) 0.0386(4) Uani 1 1 d . . . . .
O4 O 0.09248(12) 0.0282(3) 0.60971(6) 0.0755(6) Uani 1 1 d . . . . .
C1 C 0.37619(12) 0.0576(2) 0.53519(7) 0.0346(5) Uani 1 1 d . . . . .
C2 C 0.31569(11) 0.1774(2) 0.55633(6) 0.0291(4) Uani 1 1 d . . . . .
H2 H 0.264135 0.179987 0.533930 0.035 Uiso 1 1 calc R U . . .
C3 C 0.29276(11) 0.1398(2) 0.60958(6) 0.0277(4) Uani 1 1 d . . . . .
H3 H 0.265552 0.034392 0.607684 0.033 Uiso 1 1 calc R U . . .
C4 C 0.37076(11) 0.1196(2) 0.64479(7) 0.0301(5) Uani 1 1 d . . . . .
C5 C 0.44342(12) 0.0463(2) 0.62314(7) 0.0338(5) Uani 1 1 d . . . . .
H5 H 0.489673 0.018610 0.644709 0.041 Uiso 1 1 calc R U . . .
C6 C 0.44600(12) 0.0177(2) 0.57404(7) 0.0358(5) Uani 1 1 d . . . . .
H6 H 0.494012 -0.029973 0.563131 0.043 Uiso 1 1 calc R U . . .
C7 C 0.36122(11) 0.3334(2) 0.55129(6) 0.0288(4) Uani 1 1 d . . . . .
C8 C 0.42004(13) 0.3092(3) 0.50999(7) 0.0393(5) Uani 1 1 d . . . . .
H8A H 0.405874 0.381521 0.482037 0.047 Uiso 1 1 calc R U . . .
H8B H 0.477567 0.329088 0.522680 0.047 Uiso 1 1 calc R U . . .
C9 C 0.36177(11) 0.4653(2) 0.57932(7) 0.0315(5) Uani 1 1 d . . . . .
H9 H 0.397376 0.544769 0.568846 0.038 Uiso 1 1 calc R U . . .
C10 C 0.31727(12) 0.5107(2) 0.62367(7) 0.0315(5) Uani 1 1 d . . . . .
C11 C 0.33924(15) 0.6606(3) 0.64446(8) 0.0456(6) Uani 1 1 d . . . . .
H11 H 0.377018 0.724342 0.628528 0.055 Uiso 1 1 calc R U . . .
C12 C 0.30707(18) 0.7169(3) 0.68749(8) 0.0590(7) Uani 1 1 d . . . . .
H12 H 0.323132 0.816752 0.700507 0.071 Uiso 1 1 calc R U . . .
C13 C 0.25059(16) 0.6237(3) 0.71124(8) 0.0539(6) Uani 1 1 d . . . . .
H13 H 0.228468 0.659866 0.740570 0.065 Uiso 1 1 calc R U . . .
C14 C 0.22727(13) 0.4765(3) 0.69110(7) 0.0393(5) Uani 1 1 d . . . . .
H14 H 0.188906 0.414767 0.707252 0.047 Uiso 1 1 calc R U . . .
C15 C 0.25885(11) 0.4172(2) 0.64773(6) 0.0293(4) Uani 1 1 d . . . . .
C16 C 0.22701(11) 0.2569(2) 0.62685(6) 0.0295(4) Uani 1 1 d . . . . .
H16 H 0.187975 0.279700 0.597509 0.035 Uiso 1 1 calc R U . . .
C17 C 0.09709(12) 0.1437(3) 0.64755(10) 0.0535(7) Uani 1 1 d . . . . .
H17 H 0.067200 0.241171 0.636030 0.064 Uiso 1 1 calc R U . . .
C18 C 0.05691(15) 0.0709(4) 0.69164(11) 0.0784(9) Uani 1 1 d . . . . .
H18A H 0.082022 0.112382 0.723379 0.094 Uiso 1 1 calc R U . . .
H18B H -0.002896 0.091990 0.689566 0.094 Uiso 1 1 calc R U . . .
C19 C 0.0738(3) -0.1005(5) 0.68660(11) 0.1063(13) Uani 1 1 d . . . . .
H19A H 0.025360 -0.163150 0.694381 0.128 Uiso 1 1 calc R U . . .
H19B H 0.121219 -0.132146 0.709374 0.128 Uiso 1 1 calc R U . . .
C20 C 0.0929(2) -0.1262(4) 0.63303(10) 0.0851(11) Uani 1 1 d . . . . .
H20A H 0.147305 -0.176640 0.631598 0.102 Uiso 1 1 calc R U . . .
H20B H 0.050816 -0.194890 0.615904 0.102 Uiso 1 1 calc R U . . .
C21 C 0.33588(15) -0.0926(3) 0.51241(8) 0.0476(6) Uani 1 1 d . . . . .
H21A H 0.295552 -0.063620 0.485340 0.071 Uiso 1 1 calc R U . . .
H21B H 0.308318 -0.149739 0.537809 0.071 Uiso 1 1 calc R U . . .
H21C H 0.378201 -0.159762 0.499616 0.071 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.451(2) . ?
O1 C8 1.430(3) . ?
O2 C4 1.217(2) . ?
O3 C16 1.425(2) . ?
O3 C17 1.398(2) . ?
O4 C17 1.390(3) . ?
O4 C20 1.428(3) . ?
C1 C2 1.527(3) . ?
C1 C6 1.500(3) . ?
C1 C21 1.514(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.521(2) . ?
C2 C7 1.501(3) . ?
C3 H3 0.9800 . ?
C3 C4 1.511(3) . ?
C3 C16 1.530(3) . ?
C4 C5 1.468(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.330(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.512(3) . ?
C7 C9 1.327(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9 0.9300 . ?
C9 C10 1.472(3) . ?
C10 C11 1.400(3) . ?
C10 C15 1.407(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.371(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.384(3) . ?
C15 C16 1.519(3) . ?
C16 H16 0.9800 . ?
C17 H17 0.9800 . ?
C17 C18 1.505(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.462(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.493(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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 O1 C1 107.64(14) . . ?
C17 O3 C16 115.24(15) . . ?
C17 O4 C20 108.17(18) . . ?
O1 C1 C2 102.99(15) . . ?
O1 C1 C6 109.39(15) . . ?
O1 C1 C21 106.82(15) . . ?
C6 C1 C2 110.59(15) . . ?
C6 C1 C21 111.36(17) . . ?
C21 C1 C2 115.17(17) . . ?
C1 C2 H2 108.6 . . ?
C3 C2 C1 114.30(15) . . ?
C3 C2 H2 108.6 . . ?
C7 C2 C1 102.01(14) . . ?
C7 C2 H2 108.6 . . ?
C7 C2 C3 114.47(15) . . ?
C2 C3 H3 105.9 . . ?
C2 C3 C16 111.54(15) . . ?
C4 C3 C2 110.69(14) . . ?
C4 C3 H3 105.9 . . ?
C4 C3 C16 116.05(15) . . ?
C16 C3 H3 105.9 . . ?
O2 C4 C3 122.24(17) . . ?
O2 C4 C5 121.28(17) . . ?
C5 C4 C3 116.39(16) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 C4 122.90(17) . . ?
C6 C5 H5 118.6 . . ?
C1 C6 H6 118.0 . . ?
C5 C6 C1 123.97(17) . . ?
C5 C6 H6 118.0 . . ?
C2 C7 C8 106.39(16) . . ?
C9 C7 C2 130.52(16) . . ?
C9 C7 C8 122.66(18) . . ?
O1 C8 C7 105.98(16) . . ?
O1 C8 H8A 110.5 . . ?
O1 C8 H8B 110.5 . . ?
C7 C8 H8A 110.5 . . ?
C7 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
C7 C9 H9 113.6 . . ?
C7 C9 C10 132.81(18) . . ?
C10 C9 H9 113.6 . . ?
C11 C10 C9 115.07(17) . . ?
C11 C10 C15 118.09(18) . . ?
C15 C10 C9 126.79(18) . . ?
C10 C11 H11 118.8 . . ?
C12 C11 C10 122.4(2) . . ?
C12 C11 H11 118.8 . . ?
C11 C12 H12 120.4 . . ?
C11 C12 C13 119.3(2) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.4(2) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 118.8 . . ?
C13 C14 C15 122.4(2) . . ?
C15 C14 H14 118.8 . . ?
C10 C15 C16 122.49(16) . . ?
C14 C15 C10 118.48(18) . . ?
C14 C15 C16 118.99(16) . . ?
O3 C16 C3 108.78(15) . . ?
O3 C16 C15 109.22(14) . . ?
O3 C16 H16 107.2 . . ?
C3 C16 H16 107.2 . . ?
C15 C16 C3 116.81(15) . . ?
C15 C16 H16 107.2 . . ?
O3 C17 H17 110.5 . . ?
O3 C17 C18 107.7(2) . . ?
O4 C17 O3 111.22(18) . . ?
O4 C17 H17 110.5 . . ?
O4 C17 C18 106.4(2) . . ?
C18 C17 H17 110.5 . . ?
C17 C18 H18A 111.1 . . ?
C17 C18 H18B 111.1 . . ?
H18A C18 H18B 109.1 . . ?
C19 C18 C17 103.3(2) . . ?
C19 C18 H18A 111.1 . . ?
C19 C18 H18B 111.1 . . ?
C18 C19 H19A 110.5 . . ?
C18 C19 H19B 110.5 . . ?
C18 C19 C20 106.3(3) . . ?
H19A C19 H19B 108.7 . . ?
C20 C19 H19A 110.5 . . ?
C20 C19 H19B 110.5 . . ?
O4 C20 C19 106.8(3) . . ?
O4 C20 H20A 110.4 . . ?
O4 C20 H20B 110.4 . . ?
C19 C20 H20A 110.4 . . ?
C19 C20 H20B 110.4 . . ?
H20A C20 H20B 108.6 . . ?
C1 C21 H21A 109.5 . . ?
C1 C21 H21B 109.5 . . ?
C1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
O1 C1 C2 C3 -160.99(15) . . . . ?
O1 C1 C2 C7 -36.89(17) . . . . ?
O1 C1 C6 C5 129.8(2) . . . . ?
O2 C4 C5 C6 -174.6(2) . . . . ?
O3 C17 C18 C19 -89.1(3) . . . . ?
O4 C17 C18 C19 30.2(3) . . . . ?
C1 O1 C8 C7 -22.5(2) . . . . ?
C1 C2 C3 C4 53.5(2) . . . . ?
C1 C2 C3 C16 -175.67(15) . . . . ?
C1 C2 C7 C8 23.68(18) . . . . ?
C1 C2 C7 C9 -148.7(2) . . . . ?
C2 C1 C6 C5 17.1(3) . . . . ?
C2 C3 C4 O2 148.73(18) . . . . ?
C2 C3 C4 C5 -34.6(2) . . . . ?
C2 C3 C16 O3 153.11(14) . . . . ?
C2 C3 C16 C15 -82.75(18) . . . . ?
C2 C7 C8 O1 -1.9(2) . . . . ?
C2 C7 C9 C10 -2.4(4) . . . . ?
C3 C2 C7 C8 147.68(16) . . . . ?
C3 C2 C7 C9 -24.7(3) . . . . ?
C3 C4 C5 C6 8.7(3) . . . . ?
C4 C3 C16 O3 -78.88(18) . . . . ?
C4 C3 C16 C15 45.3(2) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C6 C1 C2 C3 -44.2(2) . . . . ?
C6 C1 C2 C7 79.90(18) . . . . ?
C7 C2 C3 C4 -63.7(2) . . . . ?
C7 C2 C3 C16 67.18(19) . . . . ?
C7 C9 C10 C11 176.4(2) . . . . ?
C7 C9 C10 C15 -0.8(3) . . . . ?
C8 O1 C1 C2 37.60(19) . . . . ?
C8 O1 C1 C6 -80.03(19) . . . . ?
C8 O1 C1 C21 159.32(17) . . . . ?
C8 C7 C9 C10 -173.73(19) . . . . ?
C9 C7 C8 O1 171.21(17) . . . . ?
C9 C10 C11 C12 -176.3(2) . . . . ?
C9 C10 C15 C14 175.98(18) . . . . ?
C9 C10 C15 C16 -6.3(3) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C10 C15 C16 O3 170.22(16) . . . . ?
C10 C15 C16 C3 46.3(2) . . . . ?
C11 C10 C15 C14 -1.1(3) . . . . ?
C11 C10 C15 C16 176.61(18) . . . . ?
C11 C12 C13 C14 -0.4(4) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C13 C14 C15 C10 0.4(3) . . . . ?
C13 C14 C15 C16 -177.4(2) . . . . ?
C14 C15 C16 O3 -12.0(2) . . . . ?
C14 C15 C16 C3 -135.97(18) . . . . ?
C15 C10 C11 C12 1.2(3) . . . . ?
C16 O3 C17 O4 66.9(2) . . . . ?
C16 O3 C17 C18 -177.0(2) . . . . ?
C16 C3 C4 O2 20.3(3) . . . . ?
C16 C3 C4 C5 -163.06(16) . . . . ?
C17 O3 C16 C3 -110.37(19) . . . . ?
C17 O3 C16 C15 121.10(19) . . . . ?
C17 O4 C20 C19 15.6(3) . . . . ?
C17 C18 C19 C20 -20.0(3) . . . . ?
C18 C19 C20 O4 3.9(4) . . . . ?
C20 O4 C17 O3 88.3(2) . . . . ?
C20 O4 C17 C18 -28.6(3) . . . . ?
C21 C1 C2 C3 83.1(2) . . . . ?
C21 C1 C2 C7 -152.77(16) . . . . ?
C21 C1 C6 C5 -112.3(2) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.434 0.750 36.3 7.9 ?
2 0.000 0.566 0.250 36.3 7.9 ?
3 0.500 0.066 0.250 36.3 7.9 ?
4 0.500 -0.066 0.750 36.3 7.9 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 15.945
_oxdiff_exptl_absorpt_empirical_full_min 0.551
####################################################################### 
# 
# 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_510
_database_code_depnum_ccdc_archive 'CCDC 2150313'
loop_
_audit_author_name
_audit_author_address
'Rao Weidong'
;Nanjing Forestry University
China
;
_audit_update_record             
;
2022-02-06 deposited with the CCDC.	2022-05-22 downloaded from the CCDC.
;
_audit_creation_date             2021-08-18
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 O3'
_chemical_formula_sum            'C17 H16 O3'
_chemical_formula_weight         268.30
_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'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.4200(6)
_cell_length_b                   10.6938(5)
_cell_length_c                   12.6510(7)
_cell_angle_alpha                90
_cell_angle_beta                 111.145(6)
_cell_angle_gamma                90
_cell_volume                     1314.77(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3008
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      29.0240
_cell_measurement_theta_min      2.5650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6036
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.182
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  29.00   1.00    2.00    --  -11.27 -99.00 -90.00   29
  2  ω    -11.00  29.00   1.00    2.00    --   11.90  37.00-180.00   40
  3  ω    -62.00  75.00   1.00    2.00    --   11.90   0.00 120.00  137
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0242767000
_diffrn_orient_matrix_UB_12      -0.0418454000
_diffrn_orient_matrix_UB_13      0.0465532000
_diffrn_orient_matrix_UB_21      -0.0619443000
_diffrn_orient_matrix_UB_22      0.0081442000
_diffrn_orient_matrix_UB_23      0.0103932000
_diffrn_orient_matrix_UB_31      -0.0299248000
_diffrn_orient_matrix_UB_32      -0.0508202000
_diffrn_orient_matrix_UB_33      -0.0366213000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1978
_reflns_number_total             2313
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.070
_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)+(0.0471P)²+0.4855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1036
_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:
 C7(H7), C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C11(H11), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
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
O1 O 0.62064(11) 0.88061(9) 0.30321(9) 0.0234(3) Uani 1 1 d . . . . .
O2 O 0.47397(13) 0.37134(10) 0.08347(9) 0.0281(3) Uani 1 1 d . . . . .
H2 H 0.395347 0.362652 0.082460 0.042 Uiso 1 1 calc R U . . .
O3 O 0.28556(11) 0.49218(10) 0.17994(10) 0.0287(3) Uani 1 1 d . . . . .
C1 C 0.61493(15) 0.43662(14) 0.39678(13) 0.0195(4) Uani 1 1 d . . . . .
C2 C 0.63743(17) 0.36123(15) 0.49250(14) 0.0250(4) Uani 1 1 d . . . . .
H2A H 0.663372 0.399196 0.563264 0.030 Uiso 1 1 calc R U . . .
C3 C 0.62261(18) 0.23296(16) 0.48583(15) 0.0292(4) Uani 1 1 d . . . . .
H3 H 0.638716 0.185606 0.551015 0.035 Uiso 1 1 calc R U . . .
C4 C 0.58363(18) 0.17597(16) 0.38129(16) 0.0306(4) Uani 1 1 d . . . . .
H4 H 0.573889 0.089535 0.375245 0.037 Uiso 1 1 calc R U . . .
C5 C 0.55907(17) 0.24850(15) 0.28525(14) 0.0253(4) Uani 1 1 d . . . . .
H5 H 0.532268 0.209152 0.215045 0.030 Uiso 1 1 calc R U . . .
C6 C 0.57301(15) 0.37822(14) 0.28986(13) 0.0192(4) Uani 1 1 d . . . . .
C7 C 0.55132(16) 0.44615(14) 0.17868(13) 0.0199(4) Uani 1 1 d . . . . .
H7 H 0.642905 0.455545 0.174448 0.024 Uiso 1 1 calc R U . . .
C8 C 0.48946(15) 0.57766(14) 0.16423(12) 0.0162(3) Uani 1 1 d . . . . .
H8 H 0.465901 0.598210 0.083941 0.019 Uiso 1 1 calc R U . . .
C9 C 0.59089(15) 0.67775(13) 0.22909(12) 0.0167(3) Uani 1 1 d . . . . .
H9 H 0.671694 0.675089 0.206820 0.020 Uiso 1 1 calc R U . . .
C10 C 0.63703(15) 0.66843(14) 0.35539(12) 0.0183(3) Uani 1 1 d . . . . .
C11 C 0.64128(16) 0.57040(15) 0.42139(13) 0.0208(4) Uani 1 1 d . . . . .
H11 H 0.665583 0.590443 0.497667 0.025 Uiso 1 1 calc R U . . .
C12 C 0.66653(17) 0.80016(14) 0.39997(13) 0.0242(4) Uani 1 1 d . . . . .
H12A H 0.617551 0.818400 0.450422 0.029 Uiso 1 1 calc R U . . .
H12B H 0.764278 0.811313 0.441322 0.029 Uiso 1 1 calc R U . . .
C13 C 0.52955(15) 0.81012(14) 0.20863(12) 0.0183(3) Uani 1 1 d . . . . .
C14 C 0.38795(16) 0.81097(14) 0.21460(12) 0.0197(3) Uani 1 1 d . . . . .
H14 H 0.352080 0.887502 0.225378 0.024 Uiso 1 1 calc R U . . .
C15 C 0.31064(16) 0.70981(14) 0.20553(12) 0.0200(4) Uani 1 1 d . . . . .
H15 H 0.225141 0.718229 0.212375 0.024 Uiso 1 1 calc R U . . .
C16 C 0.35597(15) 0.58517(15) 0.18504(12) 0.0185(3) Uani 1 1 d . . . . .
C17 C 0.52932(18) 0.87378(15) 0.10164(14) 0.0252(4) Uani 1 1 d . . . . .
H17A H 0.493549 0.957029 0.098159 0.038 Uiso 1 1 calc R U . . .
H17B H 0.472656 0.827172 0.036732 0.038 Uiso 1 1 calc R U . . .
H17C H 0.621624 0.877495 0.102216 0.038 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.4300(19) . ?
O1 C13 1.4427(18) . ?
O2 H2 0.8200 . ?
O2 C7 1.4283(18) . ?
O3 C16 1.2236(18) . ?
C1 C2 1.402(2) . ?
C1 C6 1.409(2) . ?
C1 C11 1.469(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.379(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(2) . ?
C6 C7 1.526(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.530(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.520(2) . ?
C8 C16 1.508(2) . ?
C9 H9 0.9800 . ?
C9 C10 1.497(2) . ?
C9 C13 1.536(2) . ?
C10 C11 1.331(2) . ?
C10 C12 1.507(2) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.504(2) . ?
C13 C17 1.514(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.329(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.468(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C12 O1 C13 108.20(11) . . ?
C7 O2 H2 109.5 . . ?
C2 C1 C6 118.14(14) . . ?
C2 C1 C11 114.63(14) . . ?
C6 C1 C11 127.22(14) . . ?
C1 C2 H2A 118.7 . . ?
C3 C2 C1 122.60(15) . . ?
C3 C2 H2A 118.7 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.10(15) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.44(15) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 118.8 . . ?
C4 C5 C6 122.48(16) . . ?
C6 C5 H5 118.8 . . ?
C1 C6 C7 124.45(13) . . ?
C5 C6 C1 118.23(14) . . ?
C5 C6 C7 117.17(14) . . ?
O2 C7 C6 111.20(12) . . ?
O2 C7 H7 106.0 . . ?
O2 C7 C8 109.19(12) . . ?
C6 C7 H7 106.0 . . ?
C6 C7 C8 117.61(12) . . ?
C8 C7 H7 106.0 . . ?
C7 C8 H8 105.5 . . ?
C9 C8 C7 113.69(12) . . ?
C9 C8 H8 105.5 . . ?
C16 C8 C7 113.79(12) . . ?
C16 C8 H8 105.5 . . ?
C16 C8 C9 111.95(12) . . ?
C8 C9 H9 109.1 . . ?
C8 C9 C13 113.07(12) . . ?
C10 C9 C8 115.00(12) . . ?
C10 C9 H9 109.1 . . ?
C10 C9 C13 101.26(12) . . ?
C13 C9 H9 109.1 . . ?
C9 C10 C12 106.31(12) . . ?
C11 C10 C9 130.35(14) . . ?
C11 C10 C12 123.04(14) . . ?
C1 C11 H11 113.9 . . ?
C10 C11 C1 132.28(15) . . ?
C10 C11 H11 113.9 . . ?
O1 C12 C10 106.37(12) . . ?
O1 C12 H12A 110.5 . . ?
O1 C12 H12B 110.5 . . ?
C10 C12 H12A 110.5 . . ?
C10 C12 H12B 110.5 . . ?
H12A C12 H12B 108.6 . . ?
O1 C13 C9 103.44(11) . . ?
O1 C13 C14 108.60(12) . . ?
O1 C13 C17 107.15(12) . . ?
C14 C13 C9 110.67(12) . . ?
C14 C13 C17 110.91(13) . . ?
C17 C13 C9 115.55(13) . . ?
C13 C14 H14 117.8 . . ?
C15 C14 C13 124.46(14) . . ?
C15 C14 H14 117.8 . . ?
C14 C15 H15 119.0 . . ?
C14 C15 C16 122.05(14) . . ?
C16 C15 H15 119.0 . . ?
O3 C16 C8 121.38(14) . . ?
O3 C16 C15 121.48(14) . . ?
C15 C16 C8 117.06(13) . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
C13 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
O1 C13 C14 C15 -131.08(15) . . . . ?
O2 C7 C8 C9 -155.76(12) . . . . ?
O2 C7 C8 C16 74.49(15) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C1 C6 C7 O2 -163.92(14) . . . . ?
C1 C6 C7 C8 -37.0(2) . . . . ?
C2 C1 C6 C5 -1.4(2) . . . . ?
C2 C1 C6 C7 -176.82(14) . . . . ?
C2 C1 C11 C10 176.96(17) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C1 0.6(2) . . . . ?
C4 C5 C6 C7 176.39(15) . . . . ?
C5 C6 C7 O2 20.58(19) . . . . ?
C5 C6 C7 C8 147.51(14) . . . . ?
C6 C1 C2 C3 1.3(2) . . . . ?
C6 C1 C11 C10 -1.8(3) . . . . ?
C6 C7 C8 C9 76.34(17) . . . . ?
C6 C7 C8 C16 -53.40(17) . . . . ?
C7 C8 C9 C10 -67.50(17) . . . . ?
C7 C8 C9 C13 176.87(12) . . . . ?
C7 C8 C16 O3 -20.46(19) . . . . ?
C7 C8 C16 C15 162.77(13) . . . . ?
C8 C9 C10 C11 24.2(2) . . . . ?
C8 C9 C10 C12 -149.52(13) . . . . ?
C8 C9 C13 O1 160.97(12) . . . . ?
C8 C9 C13 C14 44.82(16) . . . . ?
C8 C9 C13 C17 -82.27(16) . . . . ?
C9 C8 C16 O3 -151.08(14) . . . . ?
C9 C8 C16 C15 32.15(18) . . . . ?
C9 C10 C11 C1 6.2(3) . . . . ?
C9 C10 C12 O1 7.68(16) . . . . ?
C9 C13 C14 C15 -18.2(2) . . . . ?
C10 C9 C13 O1 37.39(14) . . . . ?
C10 C9 C13 C14 -78.76(14) . . . . ?
C10 C9 C13 C17 154.15(13) . . . . ?
C11 C1 C2 C3 -177.63(15) . . . . ?
C11 C1 C6 C5 177.35(15) . . . . ?
C11 C1 C6 C7 1.9(2) . . . . ?
C11 C10 C12 O1 -166.60(14) . . . . ?
C12 O1 C13 C9 -34.49(15) . . . . ?
C12 O1 C13 C14 83.12(14) . . . . ?
C12 O1 C13 C17 -157.02(13) . . . . ?
C12 C10 C11 C1 179.00(15) . . . . ?
C13 O1 C12 C10 17.12(16) . . . . ?
C13 C9 C10 C11 146.43(17) . . . . ?
C13 C9 C10 C12 -27.27(15) . . . . ?
C13 C14 C15 C16 -1.8(2) . . . . ?
C14 C15 C16 O3 177.96(14) . . . . ?
C14 C15 C16 C8 -5.3(2) . . . . ?
C16 C8 C9 C10 63.17(16) . . . . ?
C16 C8 C9 C13 -52.46(16) . . . . ?
C17 C13 C14 C15 111.43(17) . . . . ?

_olex2_date_sample_data_collection 2021-08-17
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.173
_oxdiff_exptl_absorpt_empirical_full_min 0.891
####################################################################### 
# 
# 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_639
_database_code_depnum_ccdc_archive 'CCDC 2150314'
loop_
_audit_author_name
_audit_author_address
'Rao Weidong'
;Nanjing Forestry University
China
;
_audit_update_record             
;
2022-02-06 deposited with the CCDC.	2022-05-22 downloaded from the CCDC.
;
_audit_creation_date             2021-12-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H29 Cl O4'
_chemical_formula_sum            'C28 H29 Cl O4'
_chemical_formula_weight         464.96
_chemical_absolute_configuration unk
_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      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                   6.9465(14)
_cell_length_b                   11.0726(19)
_cell_length_c                   29.323(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2255.4(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1391
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      23.5500
_cell_measurement_theta_min      2.7770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.1191
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            7823
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.780
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.432
_diffrn_reflns_theta_min         2.305
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  51.00   1.00    6.00    --   11.90 -99.00-120.00   54
  2  ω    -11.00  63.00   1.00    6.00    --   11.90  77.00   0.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0476197000
_diffrn_orient_matrix_UB_12      0.0046103000
_diffrn_orient_matrix_UB_13      0.0213409000
_diffrn_orient_matrix_UB_21      0.0281273000
_diffrn_orient_matrix_UB_22      -0.0598829000
_diffrn_orient_matrix_UB_23      0.0053846000
_diffrn_orient_matrix_UB_31      0.0858338000
_diffrn_orient_matrix_UB_32      0.0221820000
_diffrn_orient_matrix_UB_33      0.0100667000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.573
_reflns_Friedel_fraction_full    0.905
_reflns_Friedel_fraction_max     0.662
_reflns_number_gt                2914
_reflns_number_total             4872
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 708 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4872
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0645
_refine_ls_restrained_S_all      0.983
_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)+(0.0268P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1209
_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:
 C5(H5), C6(H6), C7(H7), C14(H14), C15(H15), C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,
 H11B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C20(H20), C24(H24), C26(H26), C27(H27)
2.d Tetrahedral OH refined with riding coordinates:
 O4(H4)
2.e Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_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 0.4706(2) 0.74216(13) 0.62801(5) 0.0608(4) Uani 1 1 d . . . . .
O1 O 0.4599(7) -0.2330(3) 0.30355(12) 0.0687(12) Uani 1 1 d . . . . .
O2 O 0.4924(4) 0.3882(3) 0.34003(9) 0.0300(8) Uani 1 1 d . . . . .
O3 O 0.8598(5) 0.4241(3) 0.50059(11) 0.0405(9) Uani 1 1 d . . . . .
O4 O 0.5102(6) 0.3409(3) 0.54542(10) 0.0562(11) Uani 1 1 d . . . . .
H4 H 0.627961 0.336234 0.546128 0.084 Uiso 1 1 calc R U . . .
C1 C 0.5051(6) -0.0162(4) 0.31201(14) 0.0285(11) Uani 1 1 d . . . . .
C2 C 0.5506(8) -0.1427(5) 0.29520(16) 0.0410(13) Uani 1 1 d . . . . .
C3 C 0.7268(7) -0.1353(5) 0.26469(17) 0.0472(15) Uani 1 1 d . . . . .
H3A H 0.693753 -0.156386 0.233550 0.057 Uiso 1 1 calc R U . . .
H3B H 0.826140 -0.190098 0.275321 0.057 Uiso 1 1 calc R U . . .
C4 C 0.7967(7) -0.0037(5) 0.26741(18) 0.0483(16) Uani 1 1 d . . . . .
H4A H 0.936060 0.000308 0.268831 0.058 Uiso 1 1 calc R U . . .
H4B H 0.752254 0.042694 0.241402 0.058 Uiso 1 1 calc R U . . .
C5 C 0.7054(6) 0.0420(4) 0.31179(16) 0.0307(12) Uani 1 1 d . . . . .
H5 H 0.777498 0.004161 0.336730 0.037 Uiso 1 1 calc R U . . .
C6 C 0.7007(6) 0.1757(4) 0.32203(15) 0.0290(11) Uani 1 1 d . . . . .
H6 H 0.625938 0.216481 0.298232 0.035 Uiso 1 1 calc R U . . .
C7 C 0.5990(6) 0.1952(4) 0.36858(15) 0.0268(11) Uani 1 1 d . . . . .
H7 H 0.683262 0.160135 0.391893 0.032 Uiso 1 1 calc R U . . .
C8 C 0.4065(6) 0.1305(4) 0.37245(18) 0.0379(13) Uani 1 1 d . . . . .
H8A H 0.313515 0.170951 0.353074 0.045 Uiso 1 1 calc R U . . .
H8B H 0.361115 0.136414 0.403649 0.045 Uiso 1 1 calc R U . . .
C9 C 0.4163(8) -0.0039(4) 0.35884(17) 0.0466(15) Uani 1 1 d . . . . .
H9A H 0.492955 -0.048003 0.380920 0.056 Uiso 1 1 calc R U . . .
H9B H 0.287705 -0.038114 0.358706 0.056 Uiso 1 1 calc R U . . .
C10 C 0.9034(6) 0.2302(5) 0.32315(18) 0.0451(15) Uani 1 1 d . . . . .
H10A H 0.960878 0.222440 0.293144 0.054 Uiso 1 1 calc R U . . .
H10B H 0.981790 0.184445 0.344380 0.054 Uiso 1 1 calc R U . . .
C11 C 0.9058(7) 0.3637(5) 0.33721(16) 0.0417(14) Uani 1 1 d . . . . .
H11A H 1.037351 0.390952 0.341357 0.050 Uiso 1 1 calc R U . . .
H11B H 0.846413 0.412752 0.313680 0.050 Uiso 1 1 calc R U . . .
C12 C 0.7958(6) 0.3760(4) 0.38116(16) 0.0263(10) Uani 1 1 d . . . . .
C13 C 0.5894(6) 0.3317(4) 0.37818(15) 0.0222(10) Uani 1 1 d . . . . .
C14 C 0.4731(6) 0.3772(4) 0.41923(13) 0.0226(10) Uani 1 1 d . . . . .
H14 H 0.349081 0.335028 0.419659 0.027 Uiso 1 1 calc R U . . .
C15 C 0.5703(6) 0.3585(4) 0.46477(14) 0.0265(10) Uani 1 1 d . . . . .
H15 H 0.577836 0.270750 0.468714 0.032 Uiso 1 1 calc R U . . .
C16 C 0.7760(6) 0.4017(4) 0.46464(17) 0.0281(11) Uani 1 1 d . . . . .
C17 C 0.8772(6) 0.4079(4) 0.42060(16) 0.0280(11) Uani 1 1 d . . . . .
H17 H 1.003690 0.435403 0.420230 0.034 Uiso 1 1 calc R U . . .
C18 C 0.4387(6) 0.5062(4) 0.40552(14) 0.0258(10) Uani 1 1 d . . . . .
C19 C 0.4420(7) 0.5080(4) 0.35417(14) 0.0340(12) Uani 1 1 d . . . . .
H19A H 0.316651 0.530162 0.342265 0.041 Uiso 1 1 calc R U . . .
H19B H 0.536294 0.565709 0.343224 0.041 Uiso 1 1 calc R U . . .
C20 C 0.4252(6) 0.6062(4) 0.43035(15) 0.0316(11) Uani 1 1 d . . . . .
H20 H 0.405232 0.675655 0.413131 0.038 Uiso 1 1 calc R U . . .
C21 C 0.4356(6) 0.6286(4) 0.47959(15) 0.0275(11) Uani 1 1 d . . . . .
C22 C 0.4535(7) 0.5402(4) 0.51431(15) 0.0281(11) Uani 1 1 d . . . . .
C23 C 0.4524(8) 0.4042(4) 0.50544(15) 0.0324(11) Uani 1 1 d . . . . .
H23 H 0.318307 0.381579 0.499576 0.039 Uiso 1 1 calc R U . . .
C24 C 0.4631(7) 0.5786(4) 0.55945(16) 0.0362(12) Uani 1 1 d . . . . .
H24 H 0.474971 0.521371 0.582494 0.043 Uiso 1 1 calc R U . . .
C25 C 0.4554(7) 0.6985(4) 0.57082(16) 0.0388(13) Uani 1 1 d . . . . .
C26 C 0.4402(7) 0.7860(4) 0.53792(18) 0.0411(13) Uani 1 1 d . . . . .
H26 H 0.437609 0.867499 0.545601 0.049 Uiso 1 1 calc R U . . .
C27 C 0.4290(6) 0.7490(4) 0.49285(16) 0.0341(11) Uani 1 1 d . . . . .
H27 H 0.416415 0.807728 0.470364 0.041 Uiso 1 1 calc R U . . .
C28 C 0.3707(7) 0.0347(5) 0.27449(17) 0.0423(14) Uani 1 1 d . . . . .
H28A H 0.349388 0.119212 0.279753 0.064 Uiso 1 1 calc R U . . .
H28B H 0.249906 -0.007317 0.275278 0.064 Uiso 1 1 calc R U . . .
H28C H 0.429690 0.023731 0.245165 0.064 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 C25 1.748(5) . ?
O1 C2 1.207(6) . ?
O2 C13 1.449(5) . ?
O2 C19 1.432(5) . ?
O3 C16 1.229(5) . ?
O4 H4 0.8200 . ?
O4 C23 1.423(5) . ?
C1 C2 1.518(6) . ?
C1 C5 1.533(6) . ?
C1 C9 1.511(6) . ?
C1 C28 1.549(6) . ?
C2 C3 1.518(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.538(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.534(6) . ?
C5 H5 0.9800 . ?
C5 C6 1.512(6) . ?
C6 H6 0.9800 . ?
C6 C7 1.552(6) . ?
C6 C10 1.532(6) . ?
C7 H7 0.9800 . ?
C7 C8 1.521(6) . ?
C7 C13 1.539(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.542(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.535(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.504(6) . ?
C12 C13 1.518(6) . ?
C12 C17 1.335(6) . ?
C13 C14 1.535(6) . ?
C14 H14 0.9800 . ?
C14 C15 1.510(5) . ?
C14 C18 1.503(6) . ?
C15 H15 0.9800 . ?
C15 C16 1.507(6) . ?
C15 C23 1.533(6) . ?
C16 C17 1.472(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.506(5) . ?
C18 C20 1.329(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20 0.9300 . ?
C20 C21 1.467(6) . ?
C21 C22 1.418(6) . ?
C21 C27 1.389(6) . ?
C22 C23 1.528(6) . ?
C22 C24 1.392(6) . ?
C23 H23 0.9800 . ?
C24 H24 0.9300 . ?
C24 C25 1.370(6) . ?
C25 C26 1.371(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.386(6) . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

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
C19 O2 C13 106.9(3) . . ?
C23 O4 H4 109.5 . . ?
C2 C1 C5 101.4(4) . . ?
C2 C1 C28 103.3(4) . . ?
C5 C1 C28 113.0(4) . . ?
C9 C1 C2 117.6(4) . . ?
C9 C1 C5 109.7(4) . . ?
C9 C1 C28 111.5(4) . . ?
O1 C2 C1 126.2(5) . . ?
O1 C2 C3 125.8(5) . . ?
C1 C2 C3 108.1(4) . . ?
C2 C3 H3A 110.5 . . ?
C2 C3 H3B 110.5 . . ?
C2 C3 C4 105.9(4) . . ?
H3A C3 H3B 108.7 . . ?
C4 C3 H3A 110.5 . . ?
C4 C3 H3B 110.5 . . ?
C3 C4 H4A 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
C5 C4 C3 103.1(4) . . ?
C5 C4 H4A 111.2 . . ?
C5 C4 H4B 111.2 . . ?
C1 C5 H5 106.3 . . ?
C4 C5 C1 103.9(4) . . ?
C4 C5 H5 106.3 . . ?
C6 C5 C1 113.0(4) . . ?
C6 C5 C4 120.0(4) . . ?
C6 C5 H5 106.3 . . ?
C5 C6 H6 108.7 . . ?
C5 C6 C7 108.7(4) . . ?
C5 C6 C10 111.7(4) . . ?
C7 C6 H6 108.7 . . ?
C10 C6 H6 108.7 . . ?
C10 C6 C7 110.2(4) . . ?
C6 C7 H7 106.7 . . ?
C8 C7 C6 113.6(4) . . ?
C8 C7 H7 106.7 . . ?
C8 C7 C13 114.3(4) . . ?
C13 C7 C6 108.5(4) . . ?
C13 C7 H7 106.7 . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C7 C8 C9 113.4(4) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C1 C9 C8 109.9(4) . . ?
C1 C9 H9A 109.7 . . ?
C1 C9 H9B 109.7 . . ?
C8 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C6 C10 H10A 108.9 . . ?
C6 C10 H10B 108.9 . . ?
C6 C10 C11 113.3(4) . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C10 C11 H11A 110.1 . . ?
C10 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
C12 C11 C10 108.1(4) . . ?
C12 C11 H11A 110.1 . . ?
C12 C11 H11B 110.1 . . ?
C11 C12 C13 113.7(4) . . ?
C17 C12 C11 123.4(4) . . ?
C17 C12 C13 122.4(4) . . ?
O2 C13 C7 107.7(3) . . ?
O2 C13 C12 110.2(3) . . ?
O2 C13 C14 102.6(3) . . ?
C12 C13 C7 106.7(3) . . ?
C12 C13 C14 110.2(3) . . ?
C14 C13 C7 119.3(4) . . ?
C13 C14 H14 108.4 . . ?
C15 C14 C13 114.4(3) . . ?
C15 C14 H14 108.4 . . ?
C18 C14 C13 100.7(3) . . ?
C18 C14 H14 108.4 . . ?
C18 C14 C15 115.9(3) . . ?
C14 C15 H15 105.3 . . ?
C14 C15 C23 113.8(4) . . ?
C16 C15 C14 112.2(4) . . ?
C16 C15 H15 105.3 . . ?
C16 C15 C23 113.8(4) . . ?
C23 C15 H15 105.3 . . ?
O3 C16 C15 120.7(4) . . ?
O3 C16 C17 121.1(4) . . ?
C17 C16 C15 118.0(4) . . ?
C12 C17 C16 123.0(4) . . ?
C12 C17 H17 118.5 . . ?
C16 C17 H17 118.5 . . ?
C14 C18 C19 106.1(4) . . ?
C20 C18 C14 131.1(4) . . ?
C20 C18 C19 122.6(4) . . ?
O2 C19 C18 106.3(3) . . ?
O2 C19 H19A 110.5 . . ?
O2 C19 H19B 110.5 . . ?
C18 C19 H19A 110.5 . . ?
C18 C19 H19B 110.5 . . ?
H19A C19 H19B 108.7 . . ?
C18 C20 H20 113.7 . . ?
C18 C20 C21 132.6(4) . . ?
C21 C20 H20 113.7 . . ?
C22 C21 C20 126.5(4) . . ?
C27 C21 C20 115.9(4) . . ?
C27 C21 C22 117.7(4) . . ?
C21 C22 C23 123.9(4) . . ?
C24 C22 C21 118.4(4) . . ?
C24 C22 C23 117.6(4) . . ?
O4 C23 C15 109.1(4) . . ?
O4 C23 C22 110.1(4) . . ?
O4 C23 H23 106.7 . . ?
C15 C23 H23 106.7 . . ?
C22 C23 C15 117.1(4) . . ?
C22 C23 H23 106.7 . . ?
C22 C24 H24 119.1 . . ?
C25 C24 C22 121.7(5) . . ?
C25 C24 H24 119.1 . . ?
C24 C25 Cl1 119.9(4) . . ?
C24 C25 C26 121.1(4) . . ?
C26 C25 Cl1 119.0(4) . . ?
C25 C26 H26 121.1 . . ?
C25 C26 C27 117.8(4) . . ?
C27 C26 H26 121.1 . . ?
C21 C27 H27 118.4 . . ?
C26 C27 C21 123.3(5) . . ?
C26 C27 H27 118.4 . . ?
C1 C28 H28A 109.5 . . ?
C1 C28 H28B 109.5 . . ?
C1 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
Cl1 C25 C26 C27 179.8(3) . . . . ?
O1 C2 C3 C4 -176.5(5) . . . . ?
O2 C13 C14 C15 -165.3(3) . . . . ?
O2 C13 C14 C18 -40.2(4) . . . . ?
O3 C16 C17 C12 175.1(4) . . . . ?
C1 C2 C3 C4 5.3(5) . . . . ?
C1 C5 C6 C7 56.3(5) . . . . ?
C1 C5 C6 C10 178.1(4) . . . . ?
C2 C1 C5 C4 41.4(5) . . . . ?
C2 C1 C5 C6 173.2(4) . . . . ?
C2 C1 C9 C8 172.3(4) . . . . ?
C2 C3 C4 C5 20.4(5) . . . . ?
C3 C4 C5 C1 -38.7(5) . . . . ?
C3 C4 C5 C6 -166.1(4) . . . . ?
C4 C5 C6 C7 179.5(4) . . . . ?
C4 C5 C6 C10 -58.7(6) . . . . ?
C5 C1 C2 O1 153.1(5) . . . . ?
C5 C1 C2 C3 -28.7(5) . . . . ?
C5 C1 C9 C8 57.3(5) . . . . ?
C5 C6 C7 C8 -50.2(5) . . . . ?
C5 C6 C7 C13 -178.4(4) . . . . ?
C5 C6 C10 C11 -175.4(4) . . . . ?
C6 C7 C8 C9 50.1(6) . . . . ?
C6 C7 C13 O2 56.1(4) . . . . ?
C6 C7 C13 C12 -62.1(4) . . . . ?
C6 C7 C13 C14 172.4(4) . . . . ?
C6 C10 C11 C12 52.1(6) . . . . ?
C7 C6 C10 C11 -54.5(6) . . . . ?
C7 C8 C9 C1 -53.1(6) . . . . ?
C7 C13 C14 C15 75.9(5) . . . . ?
C7 C13 C14 C18 -159.0(4) . . . . ?
C8 C7 C13 O2 -71.7(5) . . . . ?
C8 C7 C13 C12 170.1(4) . . . . ?
C8 C7 C13 C14 44.5(6) . . . . ?
C9 C1 C2 O1 33.6(8) . . . . ?
C9 C1 C2 C3 -148.2(4) . . . . ?
C9 C1 C5 C4 166.4(4) . . . . ?
C9 C1 C5 C6 -61.9(5) . . . . ?
C10 C6 C7 C8 -172.9(4) . . . . ?
C10 C6 C7 C13 58.9(5) . . . . ?
C10 C11 C12 C13 -58.0(5) . . . . ?
C10 C11 C12 C17 113.9(5) . . . . ?
C11 C12 C13 O2 -52.4(5) . . . . ?
C11 C12 C13 C7 64.2(5) . . . . ?
C11 C12 C13 C14 -165.0(4) . . . . ?
C11 C12 C17 C16 -170.3(4) . . . . ?
C12 C13 C14 C15 -48.0(5) . . . . ?
C12 C13 C14 C18 77.1(4) . . . . ?
C13 O2 C19 C18 -21.9(5) . . . . ?
C13 C7 C8 C9 175.2(4) . . . . ?
C13 C12 C17 C16 0.9(7) . . . . ?
C13 C14 C15 C16 49.0(5) . . . . ?
C13 C14 C15 C23 -179.9(4) . . . . ?
C13 C14 C18 C19 27.2(4) . . . . ?
C13 C14 C18 C20 -146.6(5) . . . . ?
C14 C15 C16 O3 160.2(4) . . . . ?
C14 C15 C16 C17 -24.0(5) . . . . ?
C14 C15 C23 O4 155.9(4) . . . . ?
C14 C15 C23 C22 -78.2(5) . . . . ?
C14 C18 C19 O2 -4.7(5) . . . . ?
C14 C18 C20 C21 -1.0(9) . . . . ?
C15 C14 C18 C19 151.3(4) . . . . ?
C15 C14 C18 C20 -22.6(7) . . . . ?
C15 C16 C17 C12 -0.8(7) . . . . ?
C16 C15 C23 O4 -73.8(5) . . . . ?
C16 C15 C23 C22 52.1(6) . . . . ?
C17 C12 C13 O2 135.7(4) . . . . ?
C17 C12 C13 C7 -107.8(5) . . . . ?
C17 C12 C13 C14 23.1(6) . . . . ?
C18 C14 C15 C16 -67.6(5) . . . . ?
C18 C14 C15 C23 63.5(5) . . . . ?
C18 C20 C21 C22 -4.0(8) . . . . ?
C18 C20 C21 C27 175.3(5) . . . . ?
C19 O2 C13 C7 165.9(4) . . . . ?
C19 O2 C13 C12 -78.1(4) . . . . ?
C19 O2 C13 C14 39.3(4) . . . . ?
C19 C18 C20 C21 -174.0(5) . . . . ?
C20 C18 C19 O2 169.8(4) . . . . ?
C20 C21 C22 C23 -4.0(8) . . . . ?
C20 C21 C22 C24 179.4(4) . . . . ?
C20 C21 C27 C26 -179.0(4) . . . . ?
C21 C22 C23 O4 168.7(4) . . . . ?
C21 C22 C23 C15 43.3(7) . . . . ?
C21 C22 C24 C25 0.1(8) . . . . ?
C22 C21 C27 C26 0.4(7) . . . . ?
C22 C24 C25 Cl1 -179.3(4) . . . . ?
C22 C24 C25 C26 -0.8(8) . . . . ?
C23 C15 C16 O3 29.0(6) . . . . ?
C23 C15 C16 C17 -155.1(4) . . . . ?
C23 C22 C24 C25 -176.8(5) . . . . ?
C24 C22 C23 O4 -14.7(6) . . . . ?
C24 C22 C23 C15 -140.0(4) . . . . ?
C24 C25 C26 C27 1.3(8) . . . . ?
C25 C26 C27 C21 -1.1(7) . . . . ?
C27 C21 C22 C23 176.8(5) . . . . ?
C27 C21 C22 C24 0.1(7) . . . . ?
C28 C1 C2 O1 -89.7(6) . . . . ?
C28 C1 C2 C3 88.5(5) . . . . ?
C28 C1 C5 C4 -68.5(5) . . . . ?
C28 C1 C5 C6 63.3(5) . . . . ?
C28 C1 C9 C8 -68.7(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.668
_oxdiff_exptl_absorpt_empirical_full_min 0.560
####################################################################### 
# 
# 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_649-1
_database_code_depnum_ccdc_archive 'CCDC 2150315'
loop_
_audit_author_name
_audit_author_address
'Rao Weidong'
;Nanjing Forestry University
China
;
_audit_update_record             
;
2022-02-06 deposited with the CCDC.	2022-05-22 downloaded from the CCDC.
;
_audit_creation_date             2022-01-16
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H28 Br2 O5'
_chemical_formula_sum            'C22 H28 Br2 O5'
_chemical_formula_weight         532.26
_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                   9.0445(7)
_cell_length_b                   19.6733(13)
_cell_length_c                   12.3531(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.312(8)
_cell_angle_gamma                90
_cell_volume                     2155.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3422
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      27.0560
_cell_measurement_theta_min      2.5040
_shelx_estimated_absorpt_T_max   0.659
_shelx_estimated_absorpt_T_min   0.619
_exptl_absorpt_coefficient_mu    3.792
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9968
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.070
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00  62.00   1.00    4.50    --  -11.35  57.00-150.00   94
  2  ω    -82.00   3.00   1.00    4.50    --  -11.35 -37.00-120.00   85
  3  ω    -12.00  17.00   1.00    4.50    --  -11.35 -99.00   0.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0248105000
_diffrn_orient_matrix_UB_12      0.0005082000
_diffrn_orient_matrix_UB_13      0.0581732000
_diffrn_orient_matrix_UB_21      -0.0759548000
_diffrn_orient_matrix_UB_22      -0.0004595000
_diffrn_orient_matrix_UB_23      0.0070548000
_diffrn_orient_matrix_UB_31      0.0013730000
_diffrn_orient_matrix_UB_32      -0.0360299000
_diffrn_orient_matrix_UB_33      0.0006938000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2964
_reflns_number_total             3803
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.789
_refine_diff_density_min         -1.103
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3803
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.020
_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)+(0.0498P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1046
_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), C9(H9), C11(H11), C14(H14), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C19(H19A,H19B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C)
;
_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 0.46117(5) 0.50286(2) 0.17747(4) 0.03157(16) Uani 1 1 d . . . . .
Br2 Br 0.77535(5) 0.16991(2) 0.41645(4) 0.03624(17) Uani 1 1 d . . . . .
O1 O 0.6510(3) 0.31069(12) 0.2240(2) 0.0197(6) Uani 1 1 d . . . . .
O2 O 0.3292(3) 0.32717(12) 0.3024(2) 0.0226(6) Uani 1 1 d . . . . .
O3 O 0.4236(3) 0.20672(13) 0.4538(2) 0.0279(7) Uani 1 1 d . . . . .
O4 O 0.7250(3) 0.33716(12) 0.5913(2) 0.0252(7) Uani 1 1 d . . . . .
O5 O 0.9264(3) 0.30002(13) 0.5147(2) 0.0258(7) Uani 1 1 d . . . . .
C1 C 0.7426(4) 0.43681(18) 0.1733(3) 0.0181(9) Uani 1 1 d . . . . .
C2 C 0.7952(5) 0.49179(19) 0.1199(3) 0.0243(10) Uani 1 1 d . . . . .
H2 H 0.726683 0.520236 0.075481 0.029 Uiso 1 1 calc R U . . .
C3 C 0.9475(5) 0.5042(2) 0.1326(4) 0.0330(11) Uani 1 1 d . . . . .
H3 H 0.981788 0.541241 0.097643 0.040 Uiso 1 1 calc R U . . .
C4 C 1.0486(5) 0.4615(2) 0.1972(3) 0.0313(10) Uani 1 1 d . . . . .
H4 H 1.151361 0.469988 0.205686 0.038 Uiso 1 1 calc R U . . .
C5 C 1.0000(5) 0.4067(2) 0.2493(3) 0.0258(10) Uani 1 1 d . . . . .
H5 H 1.069526 0.378137 0.292653 0.031 Uiso 1 1 calc R U . . .
C6 C 0.8468(5) 0.39400(19) 0.2370(3) 0.0207(9) Uani 1 1 d . . . . .
C7 C 0.7869(4) 0.33514(18) 0.2934(3) 0.0180(9) Uani 1 1 d . . . . .
H7 H 0.862196 0.298839 0.309738 0.022 Uiso 1 1 calc R U . . .
C8 C 0.7371(4) 0.35969(18) 0.3999(3) 0.0172(8) Uani 1 1 d . . . . .
H8 H 0.788835 0.402588 0.422997 0.021 Uiso 1 1 calc R U . . .
C9 C 0.5687(4) 0.37478(18) 0.3594(3) 0.0158(8) Uani 1 1 d . . . . .
H9 H 0.545759 0.421939 0.375608 0.019 Uiso 1 1 calc R U . . .
C10 C 0.5432(4) 0.36294(18) 0.2334(3) 0.0173(8) Uani 1 1 d . . . . .
C11 C 0.5778(4) 0.42025(18) 0.1584(3) 0.0198(9) Uani 1 1 d . . . . .
H11 H 0.544319 0.404963 0.082056 0.024 Uiso 1 1 calc R U . . .
C12 C 0.3850(4) 0.33407(19) 0.2027(3) 0.0229(9) Uani 1 1 d . . . . .
H12A H 0.320800 0.364409 0.152144 0.027 Uiso 1 1 calc R U . . .
H12B H 0.386902 0.290196 0.167198 0.027 Uiso 1 1 calc R U . . .
C13 C 0.4537(4) 0.32543(18) 0.3955(3) 0.0193(9) Uani 1 1 d . . . . .
C14 C 0.5173(5) 0.25207(18) 0.4068(3) 0.0200(9) Uani 1 1 d . . . . .
H14 H 0.522275 0.235474 0.332774 0.024 Uiso 1 1 calc R U . . .
C15 C 0.6723(5) 0.24468(18) 0.4791(3) 0.0205(9) Uani 1 1 d . . . . .
H15 H 0.657892 0.229818 0.551982 0.025 Uiso 1 1 calc R U . . .
C16 C 0.7694(4) 0.31028(19) 0.4963(3) 0.0202(9) Uani 1 1 d . . . . .
C17 C 0.9914(5) 0.2641(2) 0.6135(3) 0.0382(12) Uani 1 1 d . . . . .
H17A H 0.948625 0.219310 0.611325 0.057 Uiso 1 1 calc R U . . .
H17B H 0.970786 0.288143 0.676434 0.057 Uiso 1 1 calc R U . . .
H17C H 1.098506 0.260619 0.618780 0.057 Uiso 1 1 calc R U . . .
C18 C 0.7850(5) 0.4020(2) 0.6298(3) 0.0332(11) Uani 1 1 d . . . . .
H18A H 0.729323 0.437228 0.585820 0.050 Uiso 1 1 calc R U . . .
H18B H 0.889085 0.404464 0.623809 0.050 Uiso 1 1 calc R U . . .
H18C H 0.776775 0.407789 0.705534 0.050 Uiso 1 1 calc R U . . .
C19 C 0.3848(5) 0.34612(18) 0.4943(3) 0.0229(9) Uani 1 1 d . . . . .
H19A H 0.297946 0.317410 0.495337 0.027 Uiso 1 1 calc R U . . .
H19B H 0.458057 0.336893 0.561240 0.027 Uiso 1 1 calc R U . . .
C20 C 0.3354(5) 0.42017(19) 0.4971(3) 0.0257(10) Uani 1 1 d . . . . .
H20A H 0.423025 0.448358 0.523394 0.031 Uiso 1 1 calc R U . . .
H20B H 0.291005 0.434731 0.422765 0.031 Uiso 1 1 calc R U . . .
C21 C 0.2214(5) 0.4302(2) 0.5714(4) 0.0414(13) Uani 1 1 d . . . . .
H21A H 0.132805 0.403717 0.543976 0.062 Uiso 1 1 calc R U . . .
H21B H 0.194533 0.477396 0.572135 0.062 Uiso 1 1 calc R U . . .
H21C H 0.264864 0.415845 0.645056 0.062 Uiso 1 1 calc R U . . .
C22 C 0.2961(6) 0.1817(2) 0.3795(4) 0.0503(14) Uani 1 1 d . . . . .
H22A H 0.327772 0.160607 0.317754 0.075 Uiso 1 1 calc R U . . .
H22B H 0.228953 0.218657 0.353807 0.075 Uiso 1 1 calc R U . . .
H22C H 0.244866 0.148902 0.416367 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 C11 1.976(4) . ?
Br2 C15 1.978(4) . ?
O1 C7 1.437(4) . ?
O1 C10 1.437(4) . ?
O2 C12 1.426(5) . ?
O2 C13 1.443(4) . ?
O3 C14 1.430(5) . ?
O3 C22 1.415(5) . ?
O4 C16 1.415(5) . ?
O4 C18 1.430(4) . ?
O5 C16 1.408(5) . ?
O5 C17 1.433(4) . ?
C1 C2 1.397(5) . ?
C1 C6 1.388(5) . ?
C1 C11 1.502(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(6) . ?
C6 C7 1.505(5) . ?
C7 H7 0.9800 . ?
C7 C8 1.549(5) . ?
C8 H8 0.9800 . ?
C8 C9 1.536(5) . ?
C8 C16 1.521(5) . ?
C9 H9 0.9800 . ?
C9 C10 1.545(5) . ?
C9 C13 1.551(5) . ?
C10 C11 1.530(5) . ?
C10 C12 1.517(5) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.549(5) . ?
C13 C19 1.530(6) . ?
C14 H14 0.9800 . ?
C14 C15 1.515(5) . ?
C15 H15 0.9800 . ?
C15 C16 1.552(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.526(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.522(6) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
C7 O1 C10 103.1(3) . . ?
C12 O2 C13 109.7(3) . . ?
C22 O3 C14 115.2(3) . . ?
C16 O4 C18 117.3(3) . . ?
C16 O5 C17 116.2(3) . . ?
C2 C1 C11 122.1(3) . . ?
C6 C1 C2 118.8(4) . . ?
C6 C1 C11 119.0(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(4) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.6(4) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.0(4) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.7(4) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C7 117.6(4) . . ?
C5 C6 C1 120.4(4) . . ?
C5 C6 C7 122.0(3) . . ?
O1 C7 C6 109.0(3) . . ?
O1 C7 H7 111.0 . . ?
O1 C7 C8 104.7(3) . . ?
C6 C7 H7 111.0 . . ?
C6 C7 C8 110.1(3) . . ?
C8 C7 H7 111.0 . . ?
C7 C8 H8 108.3 . . ?
C9 C8 C7 102.6(3) . . ?
C9 C8 H8 108.3 . . ?
C16 C8 C7 115.0(3) . . ?
C16 C8 H8 108.3 . . ?
C16 C8 C9 113.8(3) . . ?
C8 C9 H9 110.7 . . ?
C8 C9 C10 104.0(3) . . ?
C8 C9 C13 117.6(3) . . ?
C10 C9 H9 110.7 . . ?
C10 C9 C13 102.7(3) . . ?
C13 C9 H9 110.7 . . ?
O1 C10 C9 102.7(3) . . ?
O1 C10 C11 104.8(3) . . ?
O1 C10 C12 109.5(3) . . ?
C11 C10 C9 119.4(3) . . ?
C12 C10 C9 104.8(3) . . ?
C12 C10 C11 114.8(3) . . ?
Br1 C11 H11 107.2 . . ?
C1 C11 Br1 110.3(2) . . ?
C1 C11 C10 113.7(3) . . ?
C1 C11 H11 107.2 . . ?
C10 C11 Br1 110.9(3) . . ?
C10 C11 H11 107.2 . . ?
O2 C12 C10 107.2(3) . . ?
O2 C12 H12A 110.3 . . ?
O2 C12 H12B 110.3 . . ?
C10 C12 H12A 110.3 . . ?
C10 C12 H12B 110.3 . . ?
H12A C12 H12B 108.5 . . ?
O2 C13 C9 102.6(3) . . ?
O2 C13 C14 108.1(3) . . ?
O2 C13 C19 104.7(3) . . ?
C14 C13 C9 110.6(3) . . ?
C19 C13 C9 117.6(3) . . ?
C19 C13 C14 112.2(3) . . ?
O3 C14 C13 112.3(3) . . ?
O3 C14 H14 108.1 . . ?
O3 C14 C15 104.7(3) . . ?
C13 C14 H14 108.1 . . ?
C15 C14 C13 115.2(3) . . ?
C15 C14 H14 108.1 . . ?
Br2 C15 H15 107.2 . . ?
C14 C15 Br2 107.1(2) . . ?
C14 C15 H15 107.2 . . ?
C14 C15 C16 115.8(3) . . ?
C16 C15 Br2 112.0(3) . . ?
C16 C15 H15 107.2 . . ?
O4 C16 C8 111.6(3) . . ?
O4 C16 C15 100.4(3) . . ?
O5 C16 O4 111.2(3) . . ?
O5 C16 C8 104.5(3) . . ?
O5 C16 C15 115.4(3) . . ?
C8 C16 C15 114.0(3) . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C19 H19A 108.3 . . ?
C13 C19 H19B 108.3 . . ?
H19A C19 H19B 107.4 . . ?
C20 C19 C13 116.0(3) . . ?
C20 C19 H19A 108.3 . . ?
C20 C19 H19B 108.3 . . ?
C19 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 C19 111.9(3) . . ?
C21 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
Br2 C15 C16 O4 -147.2(2) . . . . ?
Br2 C15 C16 O5 -27.7(4) . . . . ?
Br2 C15 C16 C8 93.3(3) . . . . ?
O1 C7 C8 C9 -23.9(3) . . . . ?
O1 C7 C8 C16 100.3(3) . . . . ?
O1 C10 C11 Br1 -171.4(2) . . . . ?
O1 C10 C11 C1 -46.4(4) . . . . ?
O1 C10 C12 O2 107.0(3) . . . . ?
O2 C13 C14 O3 -76.1(4) . . . . ?
O2 C13 C14 C15 164.1(3) . . . . ?
O2 C13 C19 C20 -69.7(4) . . . . ?
O3 C14 C15 Br2 88.9(3) . . . . ?
O3 C14 C15 C16 -145.4(3) . . . . ?
C1 C2 C3 C4 0.8(6) . . . . ?
C1 C6 C7 O1 34.3(4) . . . . ?
C1 C6 C7 C8 -80.0(4) . . . . ?
C2 C1 C6 C5 1.4(5) . . . . ?
C2 C1 C6 C7 -179.9(3) . . . . ?
C2 C1 C11 Br1 -48.5(4) . . . . ?
C2 C1 C11 C10 -173.8(3) . . . . ?
C2 C3 C4 C5 0.0(6) . . . . ?
C3 C4 C5 C6 -0.1(6) . . . . ?
C4 C5 C6 C1 -0.6(6) . . . . ?
C4 C5 C6 C7 -179.2(4) . . . . ?
C5 C6 C7 O1 -147.1(3) . . . . ?
C5 C6 C7 C8 98.7(4) . . . . ?
C6 C1 C2 C3 -1.6(6) . . . . ?
C6 C1 C11 Br1 135.2(3) . . . . ?
C6 C1 C11 C10 9.9(5) . . . . ?
C6 C7 C8 C9 93.1(3) . . . . ?
C6 C7 C8 C16 -142.7(3) . . . . ?
C7 O1 C10 C9 -47.5(3) . . . . ?
C7 O1 C10 C11 77.9(3) . . . . ?
C7 O1 C10 C12 -158.4(3) . . . . ?
C7 C8 C9 C10 -4.4(3) . . . . ?
C7 C8 C9 C13 108.3(3) . . . . ?
C7 C8 C16 O4 178.2(3) . . . . ?
C7 C8 C16 O5 57.9(4) . . . . ?
C7 C8 C16 C15 -68.9(4) . . . . ?
C8 C9 C10 O1 31.2(3) . . . . ?
C8 C9 C10 C11 -84.1(4) . . . . ?
C8 C9 C10 C12 145.6(3) . . . . ?
C8 C9 C13 O2 -147.8(3) . . . . ?
C8 C9 C13 C14 -32.7(4) . . . . ?
C8 C9 C13 C19 98.0(4) . . . . ?
C9 C8 C16 O4 -63.8(4) . . . . ?
C9 C8 C16 O5 176.0(3) . . . . ?
C9 C8 C16 C15 49.1(4) . . . . ?
C9 C10 C11 Br1 -57.2(4) . . . . ?
C9 C10 C11 C1 67.8(4) . . . . ?
C9 C10 C12 O2 -2.5(4) . . . . ?
C9 C13 C14 O3 172.3(3) . . . . ?
C9 C13 C14 C15 52.5(4) . . . . ?
C9 C13 C19 C20 43.4(5) . . . . ?
C10 O1 C7 C6 -72.6(3) . . . . ?
C10 O1 C7 C8 45.2(3) . . . . ?
C10 C9 C13 O2 -34.4(3) . . . . ?
C10 C9 C13 C14 80.7(3) . . . . ?
C10 C9 C13 C19 -148.6(3) . . . . ?
C11 C1 C2 C3 -177.9(4) . . . . ?
C11 C1 C6 C5 177.9(3) . . . . ?
C11 C1 C6 C7 -3.4(5) . . . . ?
C11 C10 C12 O2 -135.5(3) . . . . ?
C12 O2 C13 C9 35.0(3) . . . . ?
C12 O2 C13 C14 -81.9(4) . . . . ?
C12 O2 C13 C19 158.3(3) . . . . ?
C12 C10 C11 Br1 68.5(4) . . . . ?
C12 C10 C11 C1 -166.5(3) . . . . ?
C13 O2 C12 C10 -20.8(4) . . . . ?
C13 C9 C10 O1 -91.9(3) . . . . ?
C13 C9 C10 C11 152.8(3) . . . . ?
C13 C9 C10 C12 22.5(4) . . . . ?
C13 C14 C15 Br2 -147.2(3) . . . . ?
C13 C14 C15 C16 -21.5(5) . . . . ?
C13 C19 C20 C21 159.7(4) . . . . ?
C14 C13 C19 C20 173.3(3) . . . . ?
C14 C15 C16 O4 89.6(4) . . . . ?
C14 C15 C16 O5 -150.8(3) . . . . ?
C14 C15 C16 C8 -29.9(5) . . . . ?
C16 C8 C9 C10 -129.4(3) . . . . ?
C16 C8 C9 C13 -16.7(5) . . . . ?
C17 O5 C16 O4 49.4(4) . . . . ?
C17 O5 C16 C8 170.0(3) . . . . ?
C17 O5 C16 C15 -64.0(4) . . . . ?
C18 O4 C16 O5 61.5(4) . . . . ?
C18 O4 C16 C8 -54.8(4) . . . . ?
C18 O4 C16 C15 -176.0(3) . . . . ?
C19 C13 C14 O3 38.8(4) . . . . ?
C19 C13 C14 C15 -81.0(4) . . . . ?
C22 O3 C14 C13 80.6(4) . . . . ?
C22 O3 C14 C15 -153.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.464
_oxdiff_exptl_absorpt_empirical_full_min 0.572
