# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_mo_d8v23026_0m
_database_code_depnum_ccdc_archive 'CCDC 2274928'
loop_
_audit_author_name
_audit_author_address
'Quan Cai'
;Fudan University
China
;
_audit_update_record             
;
2023-06-26 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 Br O5'
_chemical_formula_weight         407.25

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.7480(7)
_cell_length_b                   13.0022(13)
_cell_length_c                   10.0405(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.872(3)
_cell_angle_gamma                90
_cell_volume                     874.61(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    8652
_cell_measurement_theta_min      5.149
_cell_measurement_theta_max      54.104

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.377
_shelx_estimated_absorpt_T_min   0.648
_shelx_estimated_absorpt_T_max   0.797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4722
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15392
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.575
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3412
_reflns_number_gt                3114
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.989

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0420P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1359 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.076(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3412
_refine_ls_number_parameters     228
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0816
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.73960(6) 0.67609(4) 0.40320(4) 0.04612(18) Uani 1 1 d . . . . .
O1 O 0.7846(6) 0.3179(3) 0.7616(4) 0.0616(11) Uani 1 1 d . . . . .
O2 O 0.8837(5) 0.3494(3) 0.5598(4) 0.0497(8) Uani 1 1 d . . . . .
O3 O 0.3237(5) 0.3574(3) 0.3245(3) 0.0446(8) Uani 1 1 d . . . . .
O4 O 0.1603(5) 0.4719(3) 0.1913(3) 0.0423(8) Uani 1 1 d . . . . .
O5 O -0.0400(7) 0.5573(4) -0.2042(4) 0.0747(13) Uani 1 1 d . . . . .
C1 C 0.7650(7) 0.3673(4) 0.6583(5) 0.0453(11) Uani 1 1 d . . . . .
C2 C 0.6239(7) 0.4502(4) 0.6157(5) 0.0393(10) Uani 1 1 d . . . . .
C3 C 0.4628(9) 0.4930(4) 0.6871(5) 0.0501(13) Uani 1 1 d . . . . .
H3A H 0.5089 0.4997 0.7830 0.060 Uiso 1 1 calc R U . . .
H3B H 0.3466 0.4472 0.6765 0.060 Uiso 1 1 calc R U . . .
C4 C 0.4061(9) 0.5986(4) 0.6270(5) 0.0497(12) Uani 1 1 d . . . . .
H4A H 0.2857 0.6234 0.6626 0.060 Uiso 1 1 calc R U . . .
H4B H 0.5141 0.6474 0.6539 0.060 Uiso 1 1 calc R U . . .
C5 C 0.3679(7) 0.5945(4) 0.4740(5) 0.0416(11) Uani 1 1 d . . . . .
H5A H 0.3302 0.6632 0.4397 0.050 Uiso 1 1 calc R U . . .
H5B H 0.2556 0.5481 0.4475 0.050 Uiso 1 1 calc R U . . .
C6 C 0.5499(6) 0.5575(3) 0.4099(4) 0.0311(9) Uani 1 1 d . . . . .
C7 C 0.6645(6) 0.4813(3) 0.4960(4) 0.0334(9) Uani 1 1 d . . . . .
C8 C 0.8336(6) 0.4238(4) 0.4525(5) 0.0395(10) Uani 1 1 d . . . . .
H8 H 0.9477 0.4708 0.4467 0.047 Uiso 1 1 calc R U . . .
C9 C 0.7725(7) 0.3751(4) 0.3182(5) 0.0450(11) Uani 1 1 d . . . . .
H9A H 0.6761 0.3200 0.3281 0.054 Uiso 1 1 calc R U . . .
H9B H 0.8897 0.3443 0.2849 0.054 Uiso 1 1 calc R U . . .
C10 C 0.6786(7) 0.4542(4) 0.2163(5) 0.0408(10) Uani 1 1 d . . . . .
H10 H 0.7828 0.5055 0.2026 0.049 Uiso 1 1 calc R U . . .
C11 C 0.4990(6) 0.5137(3) 0.2657(4) 0.0317(9) Uani 1 1 d . . . . .
C12 C 0.3251(6) 0.4381(3) 0.2671(4) 0.0346(9) Uani 1 1 d . . . . .
C13 C 0.4102(7) 0.5960(4) 0.1643(5) 0.0396(10) Uani 1 1 d . . . . .
H13A H 0.4422 0.6652 0.1988 0.047 Uiso 1 1 calc R U . . .
H13B H 0.4636 0.5879 0.0784 0.047 Uiso 1 1 calc R U . . .
C14 C 0.1848(6) 0.5784(4) 0.1472(5) 0.0385(10) Uani 1 1 d . . . . .
H14 H 0.1226 0.6256 0.2075 0.046 Uiso 1 1 calc R U . . .
C15 C 0.0817(7) 0.5890(4) 0.0091(5) 0.0448(12) Uani 1 1 d . . . . .
C16 C 0.0579(10) 0.5176(5) -0.0882(6) 0.0642(16) Uani 1 1 d . . . . .
H16 H 0.1026 0.4493 -0.0780 0.077 Uiso 1 1 calc R U . . .
C17 C -0.0765(9) 0.6559(5) -0.1771(6) 0.0704(19) Uani 1 1 d . . . . .
H17 H -0.1432 0.7026 -0.2382 0.084 Uiso 1 1 calc R U . . .
C18 C -0.0040(8) 0.6783(6) -0.0499(6) 0.0710(15) Uani 1 1 d . . . . .
H18 H -0.0099 0.7427 -0.0080 0.085 Uiso 1 1 calc R U . . .
C19 C 0.6195(11) 0.3993(6) 0.0808(5) 0.0664(16) Uani 1 1 d . . . . .
H19A H 0.5220 0.3462 0.0921 0.100 Uiso 1 1 calc R U . . .
H19B H 0.7370 0.3684 0.0504 0.100 Uiso 1 1 calc R U . . .
H19C H 0.5625 0.4489 0.0149 0.100 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 C6 2.010(4) . ?
O1 C1 1.214(6) . ?
O2 C1 1.365(7) . ?
O2 C8 1.458(5) . ?
O3 C12 1.197(6) . ?
O4 C12 1.344(5) . ?
O4 C14 1.470(5) . ?
O5 C17 1.338(8) . ?
O5 C16 1.369(7) . ?
C1 C2 1.468(7) . ?
C2 C7 1.327(6) . ?
C2 C3 1.481(7) . ?
C3 C4 1.529(7) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 C5 1.529(7) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 C6 1.530(6) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C6 C7 1.472(6) . ?
C6 C11 1.556(6) . ?
C7 C8 1.473(6) . ?
C8 C9 1.502(7) . ?
C8 H8 0.9900 . ?
C9 C10 1.534(7) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 C19 1.546(7) . ?
C10 C11 1.567(6) . ?
C10 H10 0.9900 . ?
C11 C12 1.532(6) . ?
C11 C13 1.547(6) . ?
C13 C14 1.527(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 C15 1.482(7) . ?
C14 H14 0.9900 . ?
C15 C16 1.343(8) . ?
C15 C18 1.397(9) . ?
C16 H16 0.9400 . ?
C17 C18 1.344(8) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?

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
C1 O2 C8 108.5(3) . . ?
C12 O4 C14 111.3(3) . . ?
C17 O5 C16 105.6(5) . . ?
O1 C1 O2 121.1(5) . . ?
O1 C1 C2 129.6(5) . . ?
O2 C1 C2 109.3(4) . . ?
C7 C2 C1 106.9(4) . . ?
C7 C2 C3 124.5(4) . . ?
C1 C2 C3 128.6(4) . . ?
C2 C3 C4 108.1(4) . . ?
C2 C3 H3A 110.1 . . ?
C4 C3 H3A 110.1 . . ?
C2 C3 H3B 110.1 . . ?
C4 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
C5 C4 C3 111.7(4) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C6 112.7(4) . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C5 110.9(4) . . ?
C7 C6 C11 110.0(4) . . ?
C5 C6 C11 114.0(3) . . ?
C7 C6 Br1 104.2(3) . . ?
C5 C6 Br1 108.6(3) . . ?
C11 C6 Br1 108.7(3) . . ?
C2 C7 C6 125.9(4) . . ?
C2 C7 C8 111.4(4) . . ?
C6 C7 C8 122.5(4) . . ?
O2 C8 C7 103.7(4) . . ?
O2 C8 C9 113.4(4) . . ?
C7 C8 C9 109.9(4) . . ?
O2 C8 H8 109.9 . . ?
C7 C8 H8 109.9 . . ?
C9 C8 H8 109.9 . . ?
C8 C9 C10 111.2(4) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 C19 108.6(4) . . ?
C9 C10 C11 113.2(4) . . ?
C19 C10 C11 112.2(4) . . ?
C9 C10 H10 107.5 . . ?
C19 C10 H10 107.5 . . ?
C11 C10 H10 107.5 . . ?
C12 C11 C13 102.3(3) . . ?
C12 C11 C6 108.1(3) . . ?
C13 C11 C6 112.6(4) . . ?
C12 C11 C10 108.0(4) . . ?
C13 C11 C10 112.7(4) . . ?
C6 C11 C10 112.5(3) . . ?
O3 C12 O4 120.3(4) . . ?
O3 C12 C11 128.1(4) . . ?
O4 C12 C11 111.6(4) . . ?
C14 C13 C11 105.9(4) . . ?
C14 C13 H13A 110.6 . . ?
C11 C13 H13A 110.6 . . ?
C14 C13 H13B 110.6 . . ?
C11 C13 H13B 110.6 . . ?
H13A C13 H13B 108.7 . . ?
O4 C14 C15 108.2(4) . . ?
O4 C14 C13 104.7(4) . . ?
C15 C14 C13 116.2(4) . . ?
O4 C14 H14 109.2 . . ?
C15 C14 H14 109.2 . . ?
C13 C14 H14 109.2 . . ?
C16 C15 C18 105.0(5) . . ?
C16 C15 C14 128.2(5) . . ?
C18 C15 C14 126.7(5) . . ?
C15 C16 O5 111.2(6) . . ?
C15 C16 H16 124.4 . . ?
O5 C16 H16 124.4 . . ?
O5 C17 C18 110.3(6) . . ?
O5 C17 H17 124.9 . . ?
C18 C17 H17 124.9 . . ?
C17 C18 C15 107.9(7) . . ?
C17 C18 H18 126.1 . . ?
C15 C18 H18 126.1 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C8 O2 C1 O1 -176.7(5) . . . . ?
C8 O2 C1 C2 3.4(5) . . . . ?
O1 C1 C2 C7 178.5(5) . . . . ?
O2 C1 C2 C7 -1.6(5) . . . . ?
O1 C1 C2 C3 -2.3(9) . . . . ?
O2 C1 C2 C3 177.6(5) . . . . ?
C7 C2 C3 C4 -19.7(7) . . . . ?
C1 C2 C3 C4 161.2(5) . . . . ?
C2 C3 C4 C5 49.9(6) . . . . ?
C3 C4 C5 C6 -59.6(6) . . . . ?
C4 C5 C6 C7 33.6(5) . . . . ?
C4 C5 C6 C11 158.4(4) . . . . ?
C4 C5 C6 Br1 -80.3(4) . . . . ?
C1 C2 C7 C6 174.7(4) . . . . ?
C3 C2 C7 C6 -4.5(7) . . . . ?
C1 C2 C7 C8 -0.9(5) . . . . ?
C3 C2 C7 C8 179.8(5) . . . . ?
C5 C6 C7 C2 -2.5(6) . . . . ?
C11 C6 C7 C2 -129.5(4) . . . . ?
Br1 C6 C7 C2 114.2(4) . . . . ?
C5 C6 C7 C8 172.7(4) . . . . ?
C11 C6 C7 C8 45.7(5) . . . . ?
Br1 C6 C7 C8 -70.6(4) . . . . ?
C1 O2 C8 C7 -3.7(4) . . . . ?
C1 O2 C8 C9 -123.0(4) . . . . ?
C2 C7 C8 O2 2.9(5) . . . . ?
C6 C7 C8 O2 -173.0(4) . . . . ?
C2 C7 C8 C9 124.4(4) . . . . ?
C6 C7 C8 C9 -51.4(5) . . . . ?
O2 C8 C9 C10 167.6(4) . . . . ?
C7 C8 C9 C10 52.1(5) . . . . ?
C8 C9 C10 C19 179.9(4) . . . . ?
C8 C9 C10 C11 -54.7(5) . . . . ?
C7 C6 C11 C12 77.4(4) . . . . ?
C5 C6 C11 C12 -47.8(5) . . . . ?
Br1 C6 C11 C12 -169.2(3) . . . . ?
C7 C6 C11 C13 -170.4(3) . . . . ?
C5 C6 C11 C13 64.4(5) . . . . ?
Br1 C6 C11 C13 -56.9(4) . . . . ?
C7 C6 C11 C10 -41.7(5) . . . . ?
C5 C6 C11 C10 -166.9(4) . . . . ?
Br1 C6 C11 C10 71.8(4) . . . . ?
C9 C10 C11 C12 -69.7(5) . . . . ?
C19 C10 C11 C12 53.6(5) . . . . ?
C9 C10 C11 C13 178.0(4) . . . . ?
C19 C10 C11 C13 -58.6(5) . . . . ?
C9 C10 C11 C6 49.4(5) . . . . ?
C19 C10 C11 C6 172.8(4) . . . . ?
C14 O4 C12 O3 171.3(4) . . . . ?
C14 O4 C12 C11 -9.3(5) . . . . ?
C13 C11 C12 O3 175.0(5) . . . . ?
C6 C11 C12 O3 -66.0(6) . . . . ?
C10 C11 C12 O3 55.9(6) . . . . ?
C13 C11 C12 O4 -4.3(5) . . . . ?
C6 C11 C12 O4 114.7(4) . . . . ?
C10 C11 C12 O4 -123.4(4) . . . . ?
C12 C11 C13 C14 15.4(5) . . . . ?
C6 C11 C13 C14 -100.4(4) . . . . ?
C10 C11 C13 C14 131.1(4) . . . . ?
C12 O4 C14 C15 143.5(4) . . . . ?
C12 O4 C14 C13 19.0(5) . . . . ?
C11 C13 C14 O4 -20.7(5) . . . . ?
C11 C13 C14 C15 -140.0(4) . . . . ?
O4 C14 C15 C16 -31.9(7) . . . . ?
C13 C14 C15 C16 85.3(7) . . . . ?
O4 C14 C15 C18 151.4(5) . . . . ?
C13 C14 C15 C18 -91.3(6) . . . . ?
C18 C15 C16 O5 -0.7(7) . . . . ?
C14 C15 C16 O5 -177.9(5) . . . . ?
C17 O5 C16 C15 0.2(7) . . . . ?
C16 O5 C17 C18 0.4(7) . . . . ?
O5 C17 C18 C15 -0.8(7) . . . . ?
C16 C15 C18 C17 0.9(7) . . . . ?
C14 C15 C18 C17 178.1(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C17 H17 O3 0.94 2.46 3.355(7) 159.9 2
C14 H14 O1 0.99 2.59 3.244(6) 123.9 2_656
C13 H13A O1 0.98 2.57 3.292(7) 131.0 2_656
C13 H13A Br1 0.98 2.70 3.241(5) 115.4 .
C9 H9A O3 0.98 2.42 3.045(6) 120.9 .

_refine_diff_density_max         0.505
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_exp_2245
_database_code_depnum_ccdc_archive 'CCDC 2275140'
loop_
_audit_author_name
_audit_author_address
'Quan Cai'
;Fudan University
China
;
_audit_update_record             
;
2023-06-26 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;
_audit_creation_date             2023-06-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 O6'
_chemical_formula_sum            'C19 H18 O6'
_chemical_formula_weight         342.33
_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 0.0181 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      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                   6.95740(10)
_cell_length_b                   10.4076(2)
_cell_length_c                   22.6105(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1637.22(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12236
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      73.9970
_cell_measurement_theta_min      4.6620
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.746
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0960
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            34313
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.072
_diffrn_reflns_theta_max         67.072
_diffrn_reflns_theta_min         3.910
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     27.00  82.00   1.00    1.00    --    0.00  82.00 -90.00   55
  2  ω    -88.00 -45.00   1.00    1.00    --    0.00 -37.00 -30.00   43
  3  ω    -81.00 -27.00   1.00    1.00    --    0.00 -19.00-150.00   54
  4  ω    -32.00  15.00   1.00    1.00    --    0.00  82.00 -90.00   47
  5  ω    -88.00  30.00   1.00    1.00    --    0.00 -82.00-150.00  118
  6  ω    -13.00  15.00   1.00    1.00    --    0.00  37.00 -90.00   28
  7  ω     47.00  88.00   1.00    1.00    --    0.00  57.00  30.00   41
  8  ω     -9.00  22.00   1.00    1.00    --    0.00 -19.00-150.00   31
  9  ω     54.00  80.00   1.00    1.00    --    0.00  37.00 -90.00   26
 10  ω    -23.00  11.00   1.00    1.00    --    0.00  57.00  60.00   34
 11  ω     -7.00  19.00   1.00    1.00    --    0.00 -37.00 -30.00   26
 12  ω    -15.00  11.00   1.00    1.00    --    0.00  57.00  30.00   26
 13  ω    -53.00  11.00   1.00    1.00    --    0.00 -77.00  90.00   64
 14  ω    -88.00 -63.00   1.00    1.00    --    0.00 -77.00  90.00   25
 15  ω     28.00  73.00   1.00    1.00    --    0.00  57.00  60.00   45
 16  ω     35.00 127.00   1.00    1.00    --   95.80 -82.00-180.00   92
 17  ω    104.00 185.00   1.00    1.00    --   95.80  66.00 163.34   81
 18  ω     66.00 102.00   1.00    1.00    --   95.80  75.00-153.15   36
 19  ω     69.00  95.00   1.00    1.00    --   95.80  66.00 163.34   26
 20  ω    123.00 184.00   1.00    1.00    --   95.80  75.00  49.33   61
 21  ω    119.00 183.00   1.00    1.00    --   95.80  82.00 108.69   64
 22  ω     67.00 115.00   1.00    1.00    --   95.80  72.00  88.60   48
 23  ω      7.00 125.00   1.00    1.00    --   95.80 -82.00 -60.00  118
 24  ω     75.00 107.00   1.00    1.00    --   95.80  45.00 -30.00   32
 25  ω     75.00 148.00   1.00    1.00    --   95.80  45.00  60.00   73
 26  ω      6.00 100.00   1.00    1.00    --   95.80 -61.00-180.00   94
 27  ω     72.00  98.00   1.00    1.00    --   95.80  61.00 120.00   26
 28  ω     65.00 108.00   1.00    1.00    --   95.80  77.00  60.00   43
 29  ω     74.00 146.00   1.00    1.00    --   95.80  61.00 -30.00   72
 30  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-120.00   26
 31  ω     63.00  89.00   1.00    1.00    --   95.80  82.00-180.00   26
 32  ω     76.00 105.00   1.00    1.00    --   95.80  45.00  30.00   29
 33  ω     66.00  93.00   1.00    1.00    --   95.80  75.00  49.33   27
 34  ω     63.00  89.00   1.00    1.00    --   95.80  82.00  30.00   26
 35  ω      6.00 113.00   1.00    1.00    --   95.80 -82.00  90.00  107
 36  ω     65.00  91.00   1.00    1.00    --   95.80  76.00  -1.15   26
 37  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 108.69   26
 38  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-150.00   26
 39  ω     66.00  92.00   1.00    1.00    --   95.80  77.00  90.00   26
 40  ω     64.00  96.00   1.00    1.00    --   95.80  82.00   0.00   32
 41  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 42  ω     75.00 179.00   1.00    1.00    --   95.80  45.00 -60.00  104
 43  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 -60.00   25
 44  ω    111.00 178.00   1.00    1.00    --   95.80  45.00  30.00   67
 45  ω     78.00 175.00   1.00    1.00    --   95.80  45.00 150.00   97
 46  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 -90.00   26
 47  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 -60.00   25
 48  ω     76.00 121.00   1.00    1.00    --   95.80  45.00 -90.00   45
 49  ω     63.00 102.00   1.00    1.00    --   95.80  82.00-150.00   39
 50  ω    110.00 147.00   1.00    1.00    --   95.80  45.00 -30.00   37
 51  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -30.00   26
 52  ω     41.00 124.00   1.00    1.00    --   95.80 -82.00   0.00   83
 53  ω     65.00  91.00   1.00    1.00    --   95.80  82.00 -30.00   26
 54  ω     66.00  92.00   1.00    1.00    --   95.80  74.00  32.22   26
 55  ω      9.00  82.00   1.00    1.00    --   95.80 -61.00  90.00   73
 56  ω     76.00 122.00   1.00    1.00    --   95.80  30.00 -90.00   46
 57  ω    131.00 185.00   1.00    1.00    --   95.80  61.00-180.00   54
 58  ω    134.00 159.00   1.00    1.00    --   95.80  82.00-120.00   25
 59  ω     64.00  90.00   1.00    1.00    --   95.80  82.00  60.00   26
 60  ω     72.00  98.00   1.00    1.00    --   95.80  61.00-180.00   26
 61  ω     71.00  96.00   1.00    1.00    --   95.80  61.00 150.00   25
 62  ω     63.00  89.00   1.00    1.00    --   95.80  82.00-120.00   26
 63  ω     73.00  99.00   1.00    1.00    --   95.80  52.00 171.84   26
 64  ω    160.00 185.00   1.00    1.00    --   95.80  72.00  88.60   25
 65  ω    128.00 153.00   1.00    1.00    --   95.80  59.00 -69.76   25
 66  ω     71.00  97.00   1.00    1.00    --   95.80  59.00 -69.76   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1031133000
_diffrn_orient_matrix_UB_12      -0.1069804000
_diffrn_orient_matrix_UB_13      -0.0347969000
_diffrn_orient_matrix_UB_21      0.0487254000
_diffrn_orient_matrix_UB_22      -0.0686978000
_diffrn_orient_matrix_UB_23      0.0584559000
_diffrn_orient_matrix_UB_31      -0.1898724000
_diffrn_orient_matrix_UB_32      -0.0756989000
_diffrn_orient_matrix_UB_33      -0.0038960000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2765
_reflns_number_total             2912
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1100 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.15(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2912
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.063
_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)+(0.0421P)²+0.1848P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0847
_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:
 C5(H5), C9(H9), C11(H11), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C10(H10A,H10B), C16(H16A,H16B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_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 0.8794(4) 0.6175(2) 0.55496(8) 0.0555(6) Uani 1 1 d . . . . .
O2 O 0.6376(2) 0.43221(17) 0.39800(7) 0.0376(4) Uani 1 1 d . . . . .
O3 O 0.5083(2) 0.28604(16) 0.33874(7) 0.0373(4) Uani 1 1 d . . . . .
O4 O -0.0316(2) 0.26865(17) 0.24471(7) 0.0380(4) Uani 1 1 d . . . . .
O5 O 0.0914(3) 0.23447(19) 0.15411(8) 0.0480(5) Uani 1 1 d . . . . .
O6 O 0.6934(3) 0.51676(19) 0.22195(8) 0.0456(5) Uani 1 1 d . . . . .
C1 C 0.7277(5) 0.5533(3) 0.57847(13) 0.0565(8) Uani 1 1 d . . . . .
H1 H 0.714493 0.532809 0.619209 0.068 Uiso 1 1 calc R U . . .
C2 C 0.5991(5) 0.5227(3) 0.53670(12) 0.0501(7) Uani 1 1 d . . . . .
H2 H 0.481527 0.477789 0.542188 0.060 Uiso 1 1 calc R U . . .
C3 C 0.6738(4) 0.5710(2) 0.48234(11) 0.0373(6) Uani 1 1 d . . . . .
C4 C 0.8417(5) 0.6279(3) 0.49599(12) 0.0479(7) Uani 1 1 d . . . . .
H4 H 0.923121 0.669638 0.468263 0.058 Uiso 1 1 calc R U . . .
C5 C 0.5924(4) 0.5605(2) 0.42159(10) 0.0341(5) Uani 1 1 d . . . . .
H5 H 0.653938 0.626836 0.395808 0.041 Uiso 1 1 calc R U . . .
C6 C 0.3739(3) 0.5719(2) 0.41608(10) 0.0307(5) Uani 1 1 d . . . . .
H6A H 0.337830 0.658060 0.401224 0.037 Uiso 1 1 calc R U . . .
H6B H 0.311844 0.558306 0.454980 0.037 Uiso 1 1 calc R U . . .
C7 C 0.4905(3) 0.3836(2) 0.36668(9) 0.0285(5) Uani 1 1 d . . . . .
C8 C 0.3115(3) 0.4674(2) 0.37212(9) 0.0258(5) Uani 1 1 d . . . . .
C9 C 0.1355(3) 0.3884(2) 0.39489(9) 0.0318(5) Uani 1 1 d . . . . .
H9 H 0.029033 0.450991 0.402171 0.038 Uiso 1 1 calc R U . . .
C10 C 0.0601(3) 0.2892(2) 0.35018(10) 0.0343(5) Uani 1 1 d . . . . .
H10A H 0.161117 0.224670 0.341864 0.041 Uiso 1 1 calc R U . . .
H10B H -0.052639 0.243967 0.366931 0.041 Uiso 1 1 calc R U . . .
C11 C 0.0033(3) 0.3568(2) 0.29330(9) 0.0321(5) Uani 1 1 d . . . . .
H11 H -0.112272 0.411941 0.300109 0.039 Uiso 1 1 calc R U . . .
C12 C 0.0922(4) 0.2951(3) 0.19999(10) 0.0357(5) Uani 1 1 d . . . . .
C13 C 0.2185(3) 0.4008(2) 0.21814(10) 0.0319(5) Uani 1 1 d . . . . .
C14 C 0.1656(3) 0.4358(2) 0.27245(9) 0.0290(5) Uani 1 1 d . . . . .
C15 C 0.2615(3) 0.5303(2) 0.31126(10) 0.0285(5) Uani 1 1 d . . . . .
H15 H 0.164673 0.599022 0.319586 0.034 Uiso 1 1 calc R U . . .
C16 C 0.4294(4) 0.5960(2) 0.27800(10) 0.0337(5) Uani 1 1 d . . . . .
H16A H 0.381781 0.677966 0.261345 0.040 Uiso 1 1 calc R U . . .
H16B H 0.530644 0.617314 0.307172 0.040 Uiso 1 1 calc R U . . .
C17 C 0.5207(4) 0.5196(2) 0.22852(10) 0.0324(5) Uani 1 1 d . . . . .
C18 C 0.3878(4) 0.4528(3) 0.18571(10) 0.0387(6) Uani 1 1 d . . . . .
H18A H 0.344319 0.514301 0.155107 0.046 Uiso 1 1 calc R U . . .
H18B H 0.456945 0.381840 0.165779 0.046 Uiso 1 1 calc R U . . .
C19 C 0.1752(5) 0.3205(3) 0.45349(11) 0.0491(8) Uani 1 1 d . . . . .
H19A H 0.280968 0.259299 0.448325 0.074 Uiso 1 1 calc R U . . .
H19B H 0.059596 0.274423 0.466244 0.074 Uiso 1 1 calc R U . . .
H19C H 0.210634 0.384162 0.483508 0.074 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 1.357(4) . ?
O1 C4 1.363(3) . ?
O2 C5 1.471(3) . ?
O2 C7 1.343(3) . ?
O3 C7 1.203(3) . ?
O4 C11 1.452(3) . ?
O4 C12 1.356(3) . ?
O5 C12 1.214(3) . ?
O6 C17 1.212(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.340(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.426(4) . ?
C3 C4 1.346(4) . ?
C3 C5 1.490(3) . ?
C4 H4 0.9500 . ?
C5 H5 1.0000 . ?
C5 C6 1.530(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C8 1.536(3) . ?
C7 C8 1.525(3) . ?
C8 C9 1.562(3) . ?
C8 C15 1.563(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.538(3) . ?
C9 C19 1.527(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.518(3) . ?
C11 H11 1.0000 . ?
C11 C14 1.475(3) . ?
C12 C13 1.466(3) . ?
C13 C14 1.333(3) . ?
C13 C18 1.489(3) . ?
C14 C15 1.477(3) . ?
C15 H15 1.0000 . ?
C15 C16 1.549(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.512(3) . ?
C17 C18 1.508(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C1 O1 C4 105.8(2) . . ?
C7 O2 C5 111.70(18) . . ?
C12 O4 C11 109.25(17) . . ?
O1 C1 H1 124.4 . . ?
C2 C1 O1 111.1(3) . . ?
C2 C1 H1 124.4 . . ?
C1 C2 H2 126.9 . . ?
C1 C2 C3 106.3(3) . . ?
C3 C2 H2 126.9 . . ?
C2 C3 C5 129.0(2) . . ?
C4 C3 C2 105.9(2) . . ?
C4 C3 C5 125.0(3) . . ?
O1 C4 H4 124.6 . . ?
C3 C4 O1 110.9(3) . . ?
C3 C4 H4 124.6 . . ?
O2 C5 C3 108.7(2) . . ?
O2 C5 H5 108.9 . . ?
O2 C5 C6 104.67(19) . . ?
C3 C5 H5 108.9 . . ?
C3 C5 C6 116.5(2) . . ?
C6 C5 H5 108.9 . . ?
C5 C6 H6A 110.5 . . ?
C5 C6 H6B 110.5 . . ?
C5 C6 C8 106.16(19) . . ?
H6A C6 H6B 108.7 . . ?
C8 C6 H6A 110.5 . . ?
C8 C6 H6B 110.5 . . ?
O2 C7 C8 111.39(18) . . ?
O3 C7 O2 121.1(2) . . ?
O3 C7 C8 127.5(2) . . ?
C6 C8 C9 112.38(18) . . ?
C6 C8 C15 109.60(18) . . ?
C7 C8 C6 103.07(18) . . ?
C7 C8 C9 111.50(18) . . ?
C7 C8 C15 110.52(17) . . ?
C9 C8 C15 109.62(18) . . ?
C8 C9 H9 107.0 . . ?
C10 C9 C8 113.84(17) . . ?
C10 C9 H9 107.0 . . ?
C19 C9 C8 112.8(2) . . ?
C19 C9 H9 107.0 . . ?
C19 C9 C10 108.7(2) . . ?
C9 C10 H10A 109.8 . . ?
C9 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C11 C10 C9 109.5(2) . . ?
C11 C10 H10A 109.8 . . ?
C11 C10 H10B 109.8 . . ?
O4 C11 C10 113.08(19) . . ?
O4 C11 H11 110.2 . . ?
O4 C11 C14 103.80(17) . . ?
C10 C11 H11 110.2 . . ?
C14 C11 C10 109.26(19) . . ?
C14 C11 H11 110.2 . . ?
O4 C12 C13 108.91(19) . . ?
O5 C12 O4 121.9(2) . . ?
O5 C12 C13 129.2(2) . . ?
C12 C13 C18 127.5(2) . . ?
C14 C13 C12 107.3(2) . . ?
C14 C13 C18 124.9(2) . . ?
C11 C14 C15 121.82(19) . . ?
C13 C14 C11 110.7(2) . . ?
C13 C14 C15 127.2(2) . . ?
C8 C15 H15 106.5 . . ?
C14 C15 C8 110.13(18) . . ?
C14 C15 H15 106.5 . . ?
C14 C15 C16 110.24(18) . . ?
C16 C15 C8 116.37(19) . . ?
C16 C15 H15 106.5 . . ?
C15 C16 H16A 108.2 . . ?
C15 C16 H16B 108.2 . . ?
H16A C16 H16B 107.3 . . ?
C17 C16 C15 116.36(19) . . ?
C17 C16 H16A 108.2 . . ?
C17 C16 H16B 108.2 . . ?
O6 C17 C16 121.3(2) . . ?
O6 C17 C18 121.2(2) . . ?
C18 C17 C16 117.4(2) . . ?
C13 C18 C17 109.66(19) . . ?
C13 C18 H18A 109.7 . . ?
C13 C18 H18B 109.7 . . ?
C17 C18 H18A 109.7 . . ?
C17 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
C9 C19 H19A 109.5 . . ?
C9 C19 H19B 109.5 . . ?
C9 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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 -0.1(4) . . . . ?
O2 C5 C6 C8 -17.3(2) . . . . ?
O2 C7 C8 C6 -3.5(2) . . . . ?
O2 C7 C8 C9 -124.27(19) . . . . ?
O2 C7 C8 C15 113.5(2) . . . . ?
O3 C7 C8 C6 176.7(2) . . . . ?
O3 C7 C8 C9 55.9(3) . . . . ?
O3 C7 C8 C15 -66.3(3) . . . . ?
O4 C11 C14 C13 0.9(3) . . . . ?
O4 C11 C14 C15 -173.60(19) . . . . ?
O4 C12 C13 C14 -0.9(3) . . . . ?
O4 C12 C13 C18 173.4(2) . . . . ?
O5 C12 C13 C14 -179.4(3) . . . . ?
O5 C12 C13 C18 -5.1(5) . . . . ?
O6 C17 C18 C13 145.3(2) . . . . ?
C1 O1 C4 C3 -0.8(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C1 C2 C3 C5 178.0(3) . . . . ?
C2 C3 C4 O1 0.7(3) . . . . ?
C2 C3 C5 O2 -79.7(3) . . . . ?
C2 C3 C5 C6 38.1(4) . . . . ?
C3 C5 C6 C8 -137.3(2) . . . . ?
C4 O1 C1 C2 0.5(3) . . . . ?
C4 C3 C5 O2 98.4(3) . . . . ?
C4 C3 C5 C6 -143.8(3) . . . . ?
C5 O2 C7 O3 171.9(2) . . . . ?
C5 O2 C7 C8 -7.9(2) . . . . ?
C5 C3 C4 O1 -177.7(2) . . . . ?
C5 C6 C8 C7 12.8(2) . . . . ?
C5 C6 C8 C9 133.0(2) . . . . ?
C5 C6 C8 C15 -104.9(2) . . . . ?
C6 C8 C9 C10 175.9(2) . . . . ?
C6 C8 C9 C19 -59.5(3) . . . . ?
C6 C8 C15 C14 -168.92(18) . . . . ?
C6 C8 C15 C16 64.7(2) . . . . ?
C7 O2 C5 C3 141.1(2) . . . . ?
C7 O2 C5 C6 15.9(2) . . . . ?
C7 C8 C9 C10 -68.9(2) . . . . ?
C7 C8 C9 C19 55.6(3) . . . . ?
C7 C8 C15 C14 78.1(2) . . . . ?
C7 C8 C15 C16 -48.2(2) . . . . ?
C8 C9 C10 C11 -58.2(2) . . . . ?
C8 C15 C16 C17 100.0(2) . . . . ?
C9 C8 C15 C14 -45.1(2) . . . . ?
C9 C8 C15 C16 -171.50(19) . . . . ?
C9 C10 C11 O4 167.99(18) . . . . ?
C9 C10 C11 C14 52.9(2) . . . . ?
C10 C11 C14 C13 121.8(2) . . . . ?
C10 C11 C14 C15 -52.7(3) . . . . ?
C11 O4 C12 O5 -179.9(2) . . . . ?
C11 O4 C12 C13 1.5(3) . . . . ?
C11 C14 C15 C8 48.8(3) . . . . ?
C11 C14 C15 C16 178.5(2) . . . . ?
C12 O4 C11 C10 -119.8(2) . . . . ?
C12 O4 C11 C14 -1.5(2) . . . . ?
C12 C13 C14 C11 -0.1(3) . . . . ?
C12 C13 C14 C15 174.1(2) . . . . ?
C12 C13 C18 C17 -157.0(2) . . . . ?
C13 C14 C15 C8 -124.8(2) . . . . ?
C13 C14 C15 C16 4.9(3) . . . . ?
C14 C13 C18 C17 16.4(3) . . . . ?
C14 C15 C16 C17 -26.3(3) . . . . ?
C15 C8 C9 C10 53.8(2) . . . . ?
C15 C8 C9 C19 178.3(2) . . . . ?
C15 C16 C17 O6 -137.8(2) . . . . ?
C15 C16 C17 C18 45.4(3) . . . . ?
C16 C17 C18 C13 -37.9(3) . . . . ?
C18 C13 C14 C11 -174.6(2) . . . . ?
C18 C13 C14 C15 -0.4(4) . . . . ?
C19 C9 C10 C11 175.1(2) . . . . ?

_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 2.143
_oxdiff_exptl_absorpt_empirical_full_min 0.385
####################################################################### 
# 
# 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_exp_3388
_database_code_depnum_ccdc_archive 'CCDC 2279407'
loop_
_audit_author_name
_audit_author_address
'Quan Cai'
;Fudan University
China
;
_audit_update_record             
;
2023-07-05 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;
_audit_creation_date             2023-07-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H20 O6'
_chemical_formula_sum            'C19 H20 O6'
_chemical_formula_weight         344.35
_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 0.0181 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      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                   6.68840(10)
_cell_length_b                   7.0394(2)
_cell_length_c                   35.4914(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1671.02(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15041
_cell_measurement_temperature    172.95(13)
_cell_measurement_theta_max      74.2130
_cell_measurement_theta_min      4.9280
_shelx_estimated_absorpt_T_max   0.905
_shelx_estimated_absorpt_T_min   0.750
_exptl_absorpt_coefficient_mu    0.849
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_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             728
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1301
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            35120
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.068
_diffrn_reflns_theta_max         67.068
_diffrn_reflns_theta_min         4.984
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.95(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  17.00   1.00    1.00    --    0.00  37.00 -60.00   36
  2  ω     47.00  74.00   1.00    1.00    --    0.00  37.00 120.00   27
  3  ω    -21.00   8.00   1.00    1.00    --    0.00  57.00-150.00   29
  4  ω    -89.00 -42.00   1.00    1.00    --    0.00 -57.00-120.00   47
  5  ω     25.00  51.00   1.00    1.00    --    0.00  57.00 -90.00   26
  6  ω    -19.00  79.00   1.00    1.00    --    0.00  37.00   0.00   98
  7  ω    -19.00  26.00   1.00    1.00    --    0.00  37.00 120.00   45
  8  ω    -25.00  56.00   1.00    1.00    --    0.00  77.00  30.00   81
  9  ω     39.00  85.00   1.00    1.00    --    0.00  37.00 -60.00   46
 10  ω    -39.00   8.00   1.00    1.00    --    0.00 -57.00-120.00   47
 11  ω     39.00  89.00   1.00    1.00    --    0.00  57.00-150.00   50
 12  ω    -23.00  18.00   1.00    1.00    --    0.00  57.00 -90.00   41
 13  ω     63.00  94.00   1.00    2.00    --   95.80  82.00-120.00   31
 14  ω     63.00 165.00   1.00    2.00    --   95.80  81.00 102.00  102
 15  ω    126.00 168.00   1.00    2.00    --   95.80  58.00-168.35   42
 16  ω    122.00 184.00   1.00    2.00    --   95.80  72.00 161.33   62
 17  ω     67.00  93.00   1.00    2.00    --   95.80  72.00 161.33   26
 18  ω     73.00 118.00   1.00    2.00    --   95.80  58.00-168.35   45
 19  ω    113.00 185.00   1.00    2.00    --   95.80  80.00  22.79   72
 20  ω    127.00 185.00   1.00    2.00    --   95.80  61.00-120.00   58
 21  ω     72.00 112.00   1.00    2.00    --   95.80  61.00-120.00   40
 22  ω     97.00 185.00   1.00    2.00    --   95.80  79.00 -42.68   88
 23  ω     65.00  90.00   1.00    2.00    --   95.80  77.00   0.00   25
 24  ω    129.00 155.00   1.00    2.00    --   95.80  77.00   0.00   26
 25  ω     63.00  89.00   1.00    2.00    --   95.80  82.00 -90.00   26
 26  ω    152.00 179.00   1.00    2.00    --   95.80  82.00 -90.00   27
 27  ω     63.00  96.00   1.00    2.00    --   95.80  82.00 120.00   33
 28  ω    114.00 185.00   1.00    2.00    --   95.80  82.00 120.00   71
 29  ω     65.00  90.00   1.00    2.00    --   95.80  77.00 -60.00   25
 30  ω    122.00 181.00   1.00    2.00    --   95.80  77.00 -60.00   59
 31  ω     36.00 128.00   1.00    2.00    --   95.80 -82.00 -30.00   92
 32  ω     66.00  91.00   1.00    2.00    --   95.80  77.00-150.00   25
 33  ω     64.00  91.00   1.00    2.00    --   95.80  79.00 -42.68   27
 34  ω     64.00 174.00   1.00    2.00    --   95.80  80.00-164.43  110
 35  ω     42.00 123.00   1.00    2.00    --   95.80 -82.00-150.00   81
 36  ω     75.00 106.00   1.00    2.00    --   95.80  45.00 -60.00   31
 37  ω     64.00  90.00   1.00    2.00    --   95.80  82.00 -30.00   26
 38  ω     82.00 124.00   1.00    2.00    --   95.80 -82.00 150.00   42
 39  ω    160.00 185.00   1.00    2.00    --   95.80  77.00  79.67   25
 40  ω     63.00  88.00   1.00    2.00    --   95.80  82.00   0.00   25
 41  ω     63.00  91.00   1.00    2.00    --   95.80  82.00  90.00   28
 42  ω     65.00  90.00   1.00    2.00    --   95.80  77.00-120.00   25
 43  ω     65.00  90.00   1.00    2.00    --   95.80  77.00-180.00   25
 44  ω    151.00 177.00   1.00    2.00    --   95.80  61.00  60.00   26
 45  ω     18.00  44.00   1.00    2.00    --   95.80 -82.00 150.00   26
 46  ω     71.00 132.00   1.00    2.00    --   95.80  61.00  60.00   61
 47  ω     75.00 115.00   1.00    2.00    --   95.80  45.00 -30.00   40
 48  ω     65.00  91.00   1.00    2.00    --   95.80  77.00 -90.00   26
 49  ω     64.00  90.00   1.00    2.00    --   95.80  82.00  30.00   26
 50  ω     81.00 112.00   1.00    2.00    --   95.80  30.00 -60.00   31
 51  ω     75.00 101.00   1.00    2.00    --   95.80  45.00 -90.00   26
 52  ω    131.00 184.00   1.00    2.00    --   95.80  45.00 -90.00   53
 53  ω     75.00 183.00   1.00    2.00    --   95.80  45.00  30.00  108
 54  ω     65.00  94.00   1.00    2.00    --   95.80  77.00 -30.00   29
 55  ω     64.00  90.00   1.00    2.00    --   95.80  82.00-150.00   26
 56  ω     65.00  91.00   1.00    2.00    --   95.80  77.00  60.00   26
 57  ω     71.00  97.00   1.00    2.00    --   95.80  61.00   0.00   26
 58  ω     71.00  96.00   1.00    2.00    --   95.80  61.00  90.00   25
 59  ω    105.00 134.00   1.00    2.00    --   95.80  61.00  90.00   29
 60  ω     63.00 103.00   1.00    2.00    --   95.80 -82.00-120.00   40
 61  ω     34.00 120.00   1.00    2.00    --   95.80 -77.00  60.00   86
 62  ω    150.00 175.00   1.00    2.00    --   95.80  82.00-120.00   25
 63  ω     65.00  91.00   1.00    2.00    --   95.80  77.00  79.67   26
 64  ω     74.00 169.00   1.00    2.00    --   95.80  50.00  88.10   95
 65  ω     64.00 106.00   1.00    2.00    --   95.80  80.00  22.79   42
 66  ω     73.00  98.00   1.00    2.00    --   95.80  52.00 173.56   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2095802000
_diffrn_orient_matrix_UB_12      0.0265903000
_diffrn_orient_matrix_UB_13      0.0172031000
_diffrn_orient_matrix_UB_21      0.0949863000
_diffrn_orient_matrix_UB_22      -0.0360142000
_diffrn_orient_matrix_UB_23      -0.0388984000
_diffrn_orient_matrix_UB_31      -0.0100278000
_diffrn_orient_matrix_UB_32      0.2142182000
_diffrn_orient_matrix_UB_33      -0.0086783000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2827
_reflns_number_total             2978
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 1105 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2978
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.047
_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)+(0.0388P)²+0.2264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0870
_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), C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C10(H10A,H10B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4A)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4030(3) 0.3649(3) 0.45699(5) 0.0438(5) Uani 1 1 d . . . . .
O2 O 0.6230(2) 0.5611(3) 0.56997(4) 0.0358(4) Uani 1 1 d . . . . .
O3 O 0.6817(2) 0.7431(3) 0.61981(4) 0.0381(4) Uani 1 1 d . . . . .
O4 O 0.2828(2) 0.2705(2) 0.65940(4) 0.0271(4) Uani 1 1 d . . . . .
H4 H 0.282536 0.234184 0.681939 0.041 Uiso 1 1 calc R U . . .
O5 O 0.7610(2) 0.6635(3) 0.76374(4) 0.0382(4) Uani 1 1 d . . . . .
O6 O 0.4748(2) 0.7251(2) 0.73296(4) 0.0311(4) Uani 1 1 d . . . . .
C1 C 0.3289(4) 0.5415(4) 0.46335(7) 0.0426(6) Uani 1 1 d . . . . .
H1 H 0.271804 0.620723 0.444533 0.051 Uiso 1 1 calc R U . . .
C2 C 0.3469(4) 0.5889(4) 0.49968(7) 0.0387(6) Uani 1 1 d . . . . .
H2 H 0.306524 0.704815 0.511079 0.046 Uiso 1 1 calc R U . . .
C3 C 0.4390(3) 0.4306(4) 0.51793(6) 0.0311(5) Uani 1 1 d . . . . .
C4 C 0.4697(4) 0.3001(4) 0.49086(6) 0.0394(6) Uani 1 1 d . . . . .
H4A H 0.529705 0.179397 0.494830 0.047 Uiso 1 1 calc R U . . .
C5 C 0.4895(4) 0.4068(3) 0.55864(6) 0.0313(5) Uani 1 1 d . . . . .
H5 H 0.559575 0.282698 0.562242 0.038 Uiso 1 1 calc R U . . .
C6 C 0.3133(3) 0.4186(3) 0.58603(6) 0.0291(5) Uani 1 1 d . . . . .
H6A H 0.267692 0.289860 0.593269 0.035 Uiso 1 1 calc R U . . .
H6B H 0.199949 0.487714 0.574456 0.035 Uiso 1 1 calc R U . . .
C7 C 0.3930(3) 0.5269(3) 0.62063(6) 0.0244(5) Uani 1 1 d . . . . .
C8 C 0.5797(3) 0.6240(3) 0.60499(6) 0.0287(5) Uani 1 1 d . . . . .
C9 C 0.2421(3) 0.6790(3) 0.63530(6) 0.0283(5) Uani 1 1 d . . . . .
H9 H 0.114655 0.611512 0.641439 0.034 Uiso 1 1 calc R U . . .
C10 C 0.3108(4) 0.7829(3) 0.67137(6) 0.0312(5) Uani 1 1 d . . . . .
H10A H 0.428424 0.863091 0.665588 0.037 Uiso 1 1 calc R U . . .
H10B H 0.202193 0.866782 0.680463 0.037 Uiso 1 1 calc R U . . .
C11 C 0.3645(3) 0.6417(3) 0.70176(6) 0.0257(5) Uani 1 1 d . . . . .
H11 H 0.240442 0.579130 0.711423 0.031 Uiso 1 1 calc R U . . .
C12 C 0.6495(3) 0.6276(3) 0.73760(6) 0.0288(5) Uani 1 1 d . . . . .
C13 C 0.6685(3) 0.4869(3) 0.70746(6) 0.0253(5) Uani 1 1 d . . . . .
C14 C 0.5036(3) 0.4961(3) 0.68700(5) 0.0225(4) Uani 1 1 d . . . . .
C15 C 0.4570(3) 0.3849(3) 0.65257(6) 0.0230(5) Uani 1 1 d . . . . .
C16 C 0.6391(3) 0.2591(3) 0.64248(6) 0.0289(5) Uani 1 1 d . . . . .
H16A H 0.593568 0.150608 0.626941 0.035 Uiso 1 1 calc R U . . .
H16B H 0.734597 0.334295 0.627256 0.035 Uiso 1 1 calc R U . . .
C17 C 0.7462(4) 0.1833(3) 0.67760(6) 0.0321(5) Uani 1 1 d . . . . .
H17A H 0.650940 0.108495 0.692942 0.038 Uiso 1 1 calc R U . . .
H17B H 0.856221 0.097822 0.669797 0.038 Uiso 1 1 calc R U . . .
C18 C 0.8313(3) 0.3453(4) 0.70146(6) 0.0312(5) Uani 1 1 d . . . . .
H18A H 0.878960 0.295842 0.725978 0.037 Uiso 1 1 calc R U . . .
H18B H 0.945437 0.405415 0.688301 0.037 Uiso 1 1 calc R U . . .
C19 C 0.1932(4) 0.8300(4) 0.60565(7) 0.0386(6) Uani 1 1 d . . . . .
H19A H 0.316235 0.895654 0.598204 0.058 Uiso 1 1 calc R U . . .
H19B H 0.098657 0.922006 0.616222 0.058 Uiso 1 1 calc R U . . .
H19C H 0.133458 0.768962 0.583530 0.058 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 1.357(3) . ?
O1 C4 1.361(3) . ?
O2 C5 1.462(3) . ?
O2 C8 1.351(3) . ?
O3 C8 1.202(3) . ?
O4 H4 0.8400 . ?
O4 C15 1.436(2) . ?
O5 C12 1.217(3) . ?
O6 C11 1.454(2) . ?
O6 C12 1.365(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.337(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.429(3) . ?
C3 C4 1.345(3) . ?
C3 C5 1.493(3) . ?
C4 H4A 0.9500 . ?
C5 H5 1.0000 . ?
C5 C6 1.530(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.540(3) . ?
C7 C8 1.528(3) . ?
C7 C9 1.561(3) . ?
C7 C15 1.571(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.544(3) . ?
C9 C19 1.531(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.510(3) . ?
C11 H11 1.0000 . ?
C11 C14 1.480(3) . ?
C12 C13 1.464(3) . ?
C13 C14 1.322(3) . ?
C13 C18 1.491(3) . ?
C14 C15 1.484(3) . ?
C15 C16 1.548(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.533(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.530(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C1 O1 C4 106.26(19) . . ?
C8 O2 C5 111.43(17) . . ?
C15 O4 H4 109.5 . . ?
C12 O6 C11 108.88(16) . . ?
O1 C1 H1 124.6 . . ?
C2 C1 O1 110.8(2) . . ?
C2 C1 H1 124.6 . . ?
C1 C2 H2 126.8 . . ?
C1 C2 C3 106.3(2) . . ?
C3 C2 H2 126.8 . . ?
C2 C3 C5 128.6(2) . . ?
C4 C3 C2 105.9(2) . . ?
C4 C3 C5 125.5(2) . . ?
O1 C4 H4A 124.7 . . ?
C3 C4 O1 110.6(2) . . ?
C3 C4 H4A 124.7 . . ?
O2 C5 C3 108.72(19) . . ?
O2 C5 H5 109.1 . . ?
O2 C5 C6 104.82(17) . . ?
C3 C5 H5 109.1 . . ?
C3 C5 C6 115.8(2) . . ?
C6 C5 H5 109.1 . . ?
C5 C6 H6A 110.7 . . ?
C5 C6 H6B 110.7 . . ?
C5 C6 C7 105.45(18) . . ?
H6A C6 H6B 108.8 . . ?
C7 C6 H6A 110.7 . . ?
C7 C6 H6B 110.7 . . ?
C6 C7 C9 112.42(17) . . ?
C6 C7 C15 110.78(17) . . ?
C8 C7 C6 102.41(17) . . ?
C8 C7 C9 110.01(17) . . ?
C8 C7 C15 108.94(17) . . ?
C9 C7 C15 111.83(17) . . ?
O2 C8 C7 111.26(18) . . ?
O3 C8 O2 120.6(2) . . ?
O3 C8 C7 128.1(2) . . ?
C7 C9 H9 107.3 . . ?
C10 C9 C7 114.14(17) . . ?
C10 C9 H9 107.3 . . ?
C19 C9 C7 112.65(18) . . ?
C19 C9 H9 107.3 . . ?
C19 C9 C10 107.75(19) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 C9 110.57(18) . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
O6 C11 C10 113.52(18) . . ?
O6 C11 H11 109.7 . . ?
O6 C11 C14 103.29(16) . . ?
C10 C11 H11 109.7 . . ?
C14 C11 C10 110.64(17) . . ?
C14 C11 H11 109.7 . . ?
O5 C12 O6 120.8(2) . . ?
O5 C12 C13 130.1(2) . . ?
O6 C12 C13 109.04(17) . . ?
C12 C13 C18 128.33(19) . . ?
C14 C13 C12 107.20(19) . . ?
C14 C13 C18 124.3(2) . . ?
C11 C14 C15 121.65(18) . . ?
C13 C14 C11 111.34(19) . . ?
C13 C14 C15 127.0(2) . . ?
O4 C15 C7 104.93(16) . . ?
O4 C15 C14 109.10(16) . . ?
O4 C15 C16 110.88(16) . . ?
C14 C15 C7 108.41(16) . . ?
C14 C15 C16 109.08(18) . . ?
C16 C15 C7 114.28(17) . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 C15 112.25(17) . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C16 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 C16 111.37(19) . . ?
C18 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
C13 C18 C17 107.80(18) . . ?
C13 C18 H18A 110.1 . . ?
C13 C18 H18B 110.1 . . ?
C17 C18 H18A 110.1 . . ?
C17 C18 H18B 110.1 . . ?
H18A C18 H18B 108.5 . . ?
C9 C19 H19A 109.5 . . ?
C9 C19 H19B 109.5 . . ?
C9 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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 -0.2(3) . . . . ?
O2 C5 C6 C7 -21.6(2) . . . . ?
O4 C15 C16 C17 -84.2(2) . . . . ?
O5 C12 C13 C14 176.8(2) . . . . ?
O5 C12 C13 C18 1.5(4) . . . . ?
O6 C11 C14 C13 2.8(2) . . . . ?
O6 C11 C14 C15 -175.15(17) . . . . ?
O6 C12 C13 C14 -3.1(2) . . . . ?
O6 C12 C13 C18 -178.4(2) . . . . ?
C1 O1 C4 C3 0.1(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C1 C2 C3 C5 -178.6(2) . . . . ?
C2 C3 C4 O1 -0.2(3) . . . . ?
C2 C3 C5 O2 -58.1(3) . . . . ?
C2 C3 C5 C6 59.5(3) . . . . ?
C3 C5 C6 C7 -141.4(2) . . . . ?
C4 O1 C1 C2 0.1(3) . . . . ?
C4 C3 C5 O2 123.3(3) . . . . ?
C4 C3 C5 C6 -119.1(3) . . . . ?
C5 O2 C8 O3 175.6(2) . . . . ?
C5 O2 C8 C7 -5.0(2) . . . . ?
C5 C3 C4 O1 178.7(2) . . . . ?
C5 C6 C7 C8 18.4(2) . . . . ?
C5 C6 C7 C9 136.42(19) . . . . ?
C5 C6 C7 C15 -97.7(2) . . . . ?
C6 C7 C8 O2 -8.9(2) . . . . ?
C6 C7 C8 O3 170.4(2) . . . . ?
C6 C7 C9 C10 176.60(18) . . . . ?
C6 C7 C9 C19 -60.1(2) . . . . ?
C6 C7 C15 O4 -55.2(2) . . . . ?
C6 C7 C15 C14 -171.70(17) . . . . ?
C6 C7 C15 C16 66.4(2) . . . . ?
C7 C9 C10 C11 -53.3(2) . . . . ?
C7 C15 C16 C17 157.52(19) . . . . ?
C8 O2 C5 C3 141.3(2) . . . . ?
C8 O2 C5 C6 16.9(2) . . . . ?
C8 C7 C9 C10 -70.0(2) . . . . ?
C8 C7 C9 C19 53.3(2) . . . . ?
C8 C7 C15 O4 -167.16(16) . . . . ?
C8 C7 C15 C14 76.4(2) . . . . ?
C8 C7 C15 C16 -45.5(2) . . . . ?
C9 C7 C8 O2 -128.61(19) . . . . ?
C9 C7 C8 O3 50.7(3) . . . . ?
C9 C7 C15 O4 71.02(19) . . . . ?
C9 C7 C15 C14 -45.4(2) . . . . ?
C9 C7 C15 C16 -167.32(18) . . . . ?
C9 C10 C11 O6 166.00(17) . . . . ?
C9 C10 C11 C14 50.4(2) . . . . ?
C10 C11 C14 C13 124.6(2) . . . . ?
C10 C11 C14 C15 -53.3(2) . . . . ?
C11 O6 C12 O5 -175.0(2) . . . . ?
C11 O6 C12 C13 4.9(2) . . . . ?
C11 C14 C15 O4 -64.0(2) . . . . ?
C11 C14 C15 C7 49.8(2) . . . . ?
C11 C14 C15 C16 174.76(18) . . . . ?
C12 O6 C11 C10 -124.52(19) . . . . ?
C12 O6 C11 C14 -4.7(2) . . . . ?
C12 C13 C14 C11 0.0(2) . . . . ?
C12 C13 C14 C15 177.84(19) . . . . ?
C12 C13 C18 C17 156.9(2) . . . . ?
C13 C14 C15 O4 118.4(2) . . . . ?
C13 C14 C15 C7 -127.8(2) . . . . ?
C13 C14 C15 C16 -2.8(3) . . . . ?
C14 C13 C18 C17 -17.6(3) . . . . ?
C14 C15 C16 C17 36.0(2) . . . . ?
C15 C7 C8 O2 108.5(2) . . . . ?
C15 C7 C8 O3 -72.2(3) . . . . ?
C15 C7 C9 C10 51.2(2) . . . . ?
C15 C7 C9 C19 174.54(18) . . . . ?
C15 C16 C17 C18 -62.4(2) . . . . ?
C16 C17 C18 C13 50.1(2) . . . . ?
C18 C13 C14 C11 175.55(19) . . . . ?
C18 C13 C14 C15 -6.7(3) . . . . ?
C19 C9 C10 C11 -179.19(19) . . . . ?

_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 4.180
_oxdiff_exptl_absorpt_empirical_full_min 0.252
