# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_d8v23129_0m
_database_code_depnum_ccdc_archive 'CCDC 2247354'
loop_
_audit_author_name
_audit_author_address
'Han Wang'
;Dalian University of Technology
China
;
_audit_update_record             
;
2023-03-09 deposited with the CCDC.	2024-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 O4'
_chemical_formula_weight         274.30

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'

_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'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.0614(3)
_cell_length_b                   10.6993(4)
_cell_length_c                   18.6749(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1410.93(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4683
_cell_measurement_theta_min      9.527
_cell_measurement_theta_max      138.752

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.756
_shelx_estimated_absorpt_T_min   0.876
_shelx_estimated_absorpt_T_max   0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4628
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            9206
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.763
_diffrn_reflns_theta_max         67.464
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             2510
_reflns_number_gt                2256
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.981

_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)+(0.0706P)²+0.1041P] 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       0.029(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 865 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.05(15)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2510
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1296
_refine_ls_wR_factor_gt          0.1241
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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 0.2692(3) 0.5973(2) 0.48723(13) 0.0669(6) Uani 1 1 d . . . . .
H1 H 0.1612 0.6128 0.4738 0.100 Uiso 1 1 calc R U . . .
O2 O 0.4423(3) 0.80462(19) 0.56632(12) 0.0636(6) Uani 1 1 d . . . . .
H2 H 0.4047 0.7672 0.5307 0.095 Uiso 1 1 calc R U . . .
O3 O 0.9266(3) 0.6724(2) 0.59758(15) 0.0787(8) Uani 1 1 d . . . . .
O4 O 0.7887(3) 0.7832(2) 0.68355(13) 0.0771(8) Uani 1 1 d . . . . .
C1 C 0.2704(4) 0.4864(3) 0.52367(15) 0.0518(7) Uani 1 1 d . . . . .
C2 C 0.1111(4) 0.4074(3) 0.52032(17) 0.0615(8) Uani 1 1 d . . . . .
H2A H 0.0044 0.4314 0.4945 0.074 Uiso 1 1 calc R U . . .
C3 C 0.1143(5) 0.2957(3) 0.55509(18) 0.0665(9) Uani 1 1 d . . . . .
H3 H 0.0093 0.2435 0.5525 0.080 Uiso 1 1 calc R U . . .
C4 C 0.2725(5) 0.2578(3) 0.59473(16) 0.0607(8) Uani 1 1 d . . . . .
C5 C 0.2820(8) 0.1397(3) 0.6290(2) 0.0861(13) Uani 1 1 d . . . . .
H5 H 0.1798 0.0853 0.6255 0.103 Uiso 1 1 calc R U . . .
C6 C 0.4382(10) 0.1044(4) 0.6670(2) 0.1035(17) Uani 1 1 d . . . . .
H6 H 0.4420 0.0264 0.6890 0.124 Uiso 1 1 calc R U . . .
C7 C 0.5899(8) 0.1845(4) 0.6726(2) 0.0965(14) Uani 1 1 d . . . . .
H7 H 0.6947 0.1603 0.6994 0.116 Uiso 1 1 calc R U . . .
C8 C 0.5907(6) 0.2993(3) 0.63967(19) 0.0707(9) Uani 1 1 d . . . . .
H8 H 0.6957 0.3511 0.6441 0.085 Uiso 1 1 calc R U . . .
C9 C 0.4329(4) 0.3390(2) 0.59920(15) 0.0521(7) Uani 1 1 d . . . . .
C10 C 0.4292(4) 0.4553(2) 0.56178(14) 0.0474(6) Uani 1 1 d . . . . .
C11 C 0.5982(4) 0.5421(3) 0.56259(16) 0.0517(6) Uani 1 1 d . . . . .
H11A H 0.5982 0.5913 0.5190 0.062 Uiso 1 1 calc R U . . .
H11B H 0.7132 0.4925 0.5631 0.062 Uiso 1 1 calc R U . . .
C12 C 0.5995(4) 0.6304(2) 0.62715(15) 0.0476(6) Uani 1 1 d . . . . .
H12 H 0.5843 0.5786 0.6701 0.057 Uiso 1 1 calc R U . . .
C13 C 0.4369(4) 0.7234(3) 0.62647(16) 0.0530(7) Uani 1 1 d . . . . .
H13A H 0.3180 0.6780 0.6263 0.064 Uiso 1 1 calc R U . . .
H13B H 0.4415 0.7730 0.6699 0.064 Uiso 1 1 calc R U . . .
C14 C 0.7904(4) 0.6959(3) 0.63341(16) 0.0532(7) Uani 1 1 d . . . . .
C15 C 0.9627(6) 0.8529(5) 0.6936(3) 0.1111(18) Uani 1 1 d . . . . .
H15A H 1.0669 0.7955 0.7016 0.133 Uiso 1 1 calc R U . . .
H15B H 0.9902 0.9013 0.6509 0.133 Uiso 1 1 calc R U . . .
C16 C 0.9433(7) 0.9351(4) 0.7540(2) 0.0909(13) Uani 1 1 d . . . . .
H16A H 0.8351 0.9881 0.7473 0.136 Uiso 1 1 calc R U . . .
H16B H 1.0551 0.9856 0.7584 0.136 Uiso 1 1 calc R U . . .
H16C H 0.9268 0.8865 0.7968 0.136 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 1.367(3) . ?
O1 H1 0.8200 . ?
O2 C13 1.421(3) . ?
O2 H2 0.8200 . ?
O3 C14 1.198(4) . ?
O4 C14 1.323(4) . ?
O4 C15 1.449(4) . ?
C1 C10 1.369(4) . ?
C1 C2 1.409(4) . ?
C2 C3 1.360(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.400(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.417(5) . ?
C4 C9 1.430(4) . ?
C5 C6 1.365(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.373(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.412(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.428(4) . ?
C10 C11 1.512(3) . ?
C11 C12 1.532(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.520(4) . ?
C12 C14 1.523(4) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 C16 1.438(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C1 O1 H1 109.5 . . ?
C13 O2 H2 109.5 . . ?
C14 O4 C15 116.6(3) . . ?
O1 C1 C10 118.3(3) . . ?
O1 C1 C2 119.6(3) . . ?
C10 C1 C2 122.1(3) . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 122.3(3) . . ?
C3 C4 C9 119.1(3) . . ?
C5 C4 C9 118.5(3) . . ?
C6 C5 C4 121.3(4) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 119.7(4) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 121.7(4) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 120.4(4) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 122.6(3) . . ?
C8 C9 C4 118.2(3) . . ?
C10 C9 C4 119.1(3) . . ?
C1 C10 C9 118.8(2) . . ?
C1 C10 C11 120.2(3) . . ?
C9 C10 C11 121.0(2) . . ?
C10 C11 C12 113.0(2) . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C14 111.6(2) . . ?
C13 C12 C11 113.1(2) . . ?
C14 C12 C11 110.5(2) . . ?
C13 C12 H12 107.1 . . ?
C14 C12 H12 107.1 . . ?
C11 C12 H12 107.1 . . ?
O2 C13 C12 112.8(2) . . ?
O2 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
O2 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
O3 C14 O4 123.4(3) . . ?
O3 C14 C12 124.8(3) . . ?
O4 C14 C12 111.8(2) . . ?
C16 C15 O4 109.6(4) . . ?
C16 C15 H15A 109.7 . . ?
O4 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
O4 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 178.3(3) . . . . ?
C10 C1 C2 C3 -0.8(4) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C2 C3 C4 C5 -177.4(3) . . . . ?
C2 C3 C4 C9 0.7(4) . . . . ?
C3 C4 C5 C6 179.6(3) . . . . ?
C9 C4 C5 C6 1.5(5) . . . . ?
C4 C5 C6 C7 0.1(6) . . . . ?
C5 C6 C7 C8 -1.2(7) . . . . ?
C6 C7 C8 C9 0.6(6) . . . . ?
C7 C8 C9 C10 -177.7(3) . . . . ?
C7 C8 C9 C4 1.1(5) . . . . ?
C3 C4 C9 C8 179.7(3) . . . . ?
C5 C4 C9 C8 -2.1(4) . . . . ?
C3 C4 C9 C10 -1.4(4) . . . . ?
C5 C4 C9 C10 176.7(3) . . . . ?
O1 C1 C10 C9 -179.1(2) . . . . ?
C2 C1 C10 C9 0.0(4) . . . . ?
O1 C1 C10 C11 -0.4(4) . . . . ?
C2 C1 C10 C11 178.8(3) . . . . ?
C8 C9 C10 C1 179.9(3) . . . . ?
C4 C9 C10 C1 1.1(4) . . . . ?
C8 C9 C10 C11 1.1(4) . . . . ?
C4 C9 C10 C11 -177.7(3) . . . . ?
C1 C10 C11 C12 94.9(3) . . . . ?
C9 C10 C11 C12 -86.4(3) . . . . ?
C10 C11 C12 C13 -65.7(3) . . . . ?
C10 C11 C12 C14 168.4(2) . . . . ?
C14 C12 C13 O2 63.2(3) . . . . ?
C11 C12 C13 O2 -62.1(3) . . . . ?
C15 O4 C14 O3 0.6(5) . . . . ?
C15 O4 C14 C12 -179.2(4) . . . . ?
C13 C12 C14 O3 -133.9(3) . . . . ?
C11 C12 C14 O3 -7.1(4) . . . . ?
C13 C12 C14 O4 46.0(3) . . . . ?
C11 C12 C14 O4 172.7(2) . . . . ?
C14 O4 C15 C16 -174.5(4) . . . . ?

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
O2 H2 O3 0.82 2.49 3.073(4) 129.3 4_466
O2 H2 O1 0.82 2.21 2.932(3) 147.2 .
O1 H1 O2 0.82 1.93 2.726(3) 162.9 4_466

_refine_diff_density_max         0.158
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.039

_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_cu_d8v23127_0m
_database_code_depnum_ccdc_archive 'CCDC 2247355'
loop_
_audit_author_name
_audit_author_address
'Han Wang'
;Dalian University of Technology
China
;
_audit_update_record             
;
2023-03-09 deposited with the CCDC.	2024-06-11 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 H18 O4'
_chemical_formula_weight         310.33

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.2353(3)
_cell_length_b                   9.8484(4)
_cell_length_c                   11.7427(5)
_cell_angle_alpha                82.2410(10)
_cell_angle_beta                 70.296(2)
_cell_angle_gamma                66.5120(10)
_cell_volume                     822.33(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9914
_cell_measurement_theta_min      7.997
_cell_measurement_theta_max      140.167

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.714
_shelx_estimated_absorpt_T_min   0.870
_shelx_estimated_absorpt_T_max   0.919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5300
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            28232
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.999
_diffrn_reflns_theta_max         67.492
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             2856
_reflns_number_gt                2706
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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)+(0.0724P)²+0.1431P] 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       0.059(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2856
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1336
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
O1 O 0.16191(16) 0.35791(14) 0.53114(9) 0.0683(4) Uani 1 1 d . . . . .
O2 O 0.30122(16) 0.50844(13) 0.43802(9) 0.0625(3) Uani 1 1 d . . . . .
O3 O 0.52880(16) 0.22119(15) 0.15223(9) 0.0743(4) Uani 1 1 d . . . . .
O4 O 0.53066(15) 0.17786(13) 0.34324(10) 0.0697(4) Uani 1 1 d . . . . .
C1 C 0.2337(2) 0.40428(17) 0.43587(12) 0.0549(4) Uani 1 1 d . . . . .
C2 C 0.25369(19) 0.35529(16) 0.31214(11) 0.0500(4) Uani 1 1 d . . . . .
C3 C 0.2176(2) 0.49017(16) 0.22873(12) 0.0524(4) Uani 1 1 d . . . . .
H3A H 0.2437 0.4584 0.1476 0.063 Uiso 1 1 calc R U . . .
H3B H 0.0877 0.5560 0.2574 0.063 Uiso 1 1 calc R U . . .
C4 C 0.33919(19) 0.57059(15) 0.22654(12) 0.0513(4) Uani 1 1 d . . . . .
C5 C 0.3799(2) 0.57356(16) 0.33096(13) 0.0545(4) Uani 1 1 d . . . . .
C6 C 0.4924(2) 0.64270(19) 0.33746(16) 0.0677(5) Uani 1 1 d . . . . .
H6 H 0.5163 0.6436 0.4093 0.081 Uiso 1 1 calc R U . . .
C7 C 0.5692(3) 0.71096(19) 0.23453(18) 0.0727(5) Uani 1 1 d . . . . .
H7 H 0.6463 0.7578 0.2368 0.087 Uiso 1 1 calc R U . . .
C8 C 0.5321(3) 0.70992(18) 0.12875(16) 0.0677(4) Uani 1 1 d . . . . .
H8 H 0.5842 0.7560 0.0599 0.081 Uiso 1 1 calc R U . . .
C9 C 0.4184(2) 0.64094(17) 0.12481(14) 0.0581(4) Uani 1 1 d . . . . .
H9 H 0.3937 0.6412 0.0531 0.070 Uiso 1 1 calc R U . . .
C10 C 0.1175(2) 0.27555(18) 0.33060(13) 0.0581(4) Uani 1 1 d . . . . .
H10A H 0.1599 0.1837 0.3738 0.070 Uiso 1 1 calc R U . . .
H10B H -0.0044 0.3372 0.3815 0.070 Uiso 1 1 calc R U . . .
C11 C 0.09690(19) 0.24071(15) 0.21653(12) 0.0512(4) Uani 1 1 d . . . . .
C12 C -0.0337(2) 0.34340(18) 0.16694(16) 0.0651(4) Uani 1 1 d . . . . .
H12 H -0.1071 0.4352 0.2040 0.078 Uiso 1 1 calc R U . . .
C13 C -0.0572(3) 0.3127(2) 0.06394(19) 0.0795(5) Uani 1 1 d . . . . .
H13 H -0.1451 0.3838 0.0319 0.095 Uiso 1 1 calc R U . . .
C14 C 0.0479(3) 0.1785(3) 0.00885(17) 0.0811(6) Uani 1 1 d . . . . .
H14 H 0.0314 0.1578 -0.0605 0.097 Uiso 1 1 calc R U . . .
C15 C 0.1775(3) 0.0743(2) 0.05579(17) 0.0772(5) Uani 1 1 d . . . . .
H15 H 0.2493 -0.0174 0.0182 0.093 Uiso 1 1 calc R U . . .
C16 C 0.2025(2) 0.10460(17) 0.15923(15) 0.0628(4) Uani 1 1 d . . . . .
H16 H 0.2910 0.0330 0.1905 0.075 Uiso 1 1 calc R U . . .
C17 C 0.4537(2) 0.24512(16) 0.25810(12) 0.0531(4) Uani 1 1 d . . . . .
C18 C 0.7199(3) 0.0674(2) 0.30345(19) 0.0834(6) Uani 1 1 d . . . . .
H18A H 0.7993 0.1078 0.2399 0.100 Uiso 1 1 calc R U . . .
H18B H 0.7205 -0.0190 0.2720 0.100 Uiso 1 1 calc R U . . .
C19 C 0.7880(4) 0.0266(4) 0.4081(3) 0.1287(11) Uani 1 1 d . . . . .
H19A H 0.9166 -0.0391 0.3829 0.193 Uiso 1 1 calc R U . . .
H19B H 0.7160 -0.0220 0.4671 0.193 Uiso 1 1 calc R U . . .
H19C H 0.7763 0.1141 0.4429 0.193 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 1.2003(18) . ?
O2 C1 1.3541(19) . ?
O2 C5 1.4056(18) . ?
O3 C17 1.1950(17) . ?
O4 C17 1.3245(18) . ?
O4 C18 1.458(2) . ?
C1 C2 1.5282(18) . ?
C2 C3 1.5306(19) . ?
C2 C17 1.533(2) . ?
C2 C10 1.554(2) . ?
C3 C4 1.497(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.3826(19) . ?
C4 C9 1.394(2) . ?
C5 C6 1.376(2) . ?
C6 C7 1.385(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(2) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.505(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.384(2) . ?
C11 C16 1.388(2) . ?
C12 C13 1.377(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.362(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.367(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 C19 1.462(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C1 O2 C5 121.40(11) . . ?
C17 O4 C18 116.98(13) . . ?
O1 C1 O2 117.63(13) . . ?
O1 C1 C2 124.93(14) . . ?
O2 C1 C2 117.44(12) . . ?
C1 C2 C3 109.28(12) . . ?
C1 C2 C17 108.45(11) . . ?
C3 C2 C17 108.89(11) . . ?
C1 C2 C10 108.28(11) . . ?
C3 C2 C10 113.05(11) . . ?
C17 C2 C10 108.80(12) . . ?
C4 C3 C2 109.86(11) . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C9 117.21(14) . . ?
C5 C4 C3 118.49(13) . . ?
C9 C4 C3 124.28(12) . . ?
C6 C5 C4 122.81(14) . . ?
C6 C5 O2 116.70(13) . . ?
C4 C5 O2 120.46(13) . . ?
C5 C6 C7 118.41(15) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C8 C7 C6 120.41(15) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C7 120.07(16) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C4 121.10(14) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
C11 C10 C2 115.37(11) . . ?
C11 C10 H10A 108.4 . . ?
C2 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C2 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C12 C11 C16 117.53(14) . . ?
C12 C11 C10 120.50(14) . . ?
C16 C11 C10 121.94(14) . . ?
C13 C12 C11 121.44(16) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 120.22(18) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.84(16) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 120.26(17) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.71(16) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
O3 C17 O4 124.44(14) . . ?
O3 C17 C2 123.89(13) . . ?
O4 C17 C2 111.66(11) . . ?
O4 C18 C19 107.66(17) . . ?
O4 C18 H18A 110.2 . . ?
C19 C18 H18A 110.2 . . ?
O4 C18 H18B 110.2 . . ?
C19 C18 H18B 110.2 . . ?
H18A C18 H18B 108.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 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
C5 O2 C1 O1 -177.12(12) . . . . ?
C5 O2 C1 C2 2.53(19) . . . . ?
O1 C1 C2 C3 140.31(15) . . . . ?
O2 C1 C2 C3 -39.31(17) . . . . ?
O1 C1 C2 C17 -101.12(16) . . . . ?
O2 C1 C2 C17 79.26(15) . . . . ?
O1 C1 C2 C10 16.78(19) . . . . ?
O2 C1 C2 C10 -162.84(12) . . . . ?
C1 C2 C3 C4 52.98(15) . . . . ?
C17 C2 C3 C4 -65.31(14) . . . . ?
C10 C2 C3 C4 173.64(11) . . . . ?
C2 C3 C4 C5 -34.11(17) . . . . ?
C2 C3 C4 C9 144.50(14) . . . . ?
C9 C4 C5 C6 0.3(2) . . . . ?
C3 C4 C5 C6 179.05(14) . . . . ?
C9 C4 C5 O2 178.29(12) . . . . ?
C3 C4 C5 O2 -3.0(2) . . . . ?
C1 O2 C5 C6 -161.18(14) . . . . ?
C1 O2 C5 C4 20.8(2) . . . . ?
C4 C5 C6 C7 -0.6(2) . . . . ?
O2 C5 C6 C7 -178.62(14) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C7 C8 C9 C4 -0.3(2) . . . . ?
C5 C4 C9 C8 0.1(2) . . . . ?
C3 C4 C9 C8 -178.53(14) . . . . ?
C1 C2 C10 C11 170.89(12) . . . . ?
C3 C2 C10 C11 49.66(17) . . . . ?
C17 C2 C10 C11 -71.44(15) . . . . ?
C2 C10 C11 C12 -87.80(17) . . . . ?
C2 C10 C11 C16 94.15(17) . . . . ?
C16 C11 C12 C13 -0.6(2) . . . . ?
C10 C11 C12 C13 -178.75(15) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C14 C15 C16 C11 -0.1(3) . . . . ?
C12 C11 C16 C15 0.4(2) . . . . ?
C10 C11 C16 C15 178.46(14) . . . . ?
C18 O4 C17 O3 0.0(2) . . . . ?
C18 O4 C17 C2 178.56(14) . . . . ?
C1 C2 C17 O3 -156.64(15) . . . . ?
C3 C2 C17 O3 -37.82(19) . . . . ?
C10 C2 C17 O3 85.79(18) . . . . ?
C1 C2 C17 O4 24.75(17) . . . . ?
C3 C2 C17 O4 143.56(12) . . . . ?
C10 C2 C17 O4 -92.82(14) . . . . ?
C17 O4 C18 C19 170.5(2) . . . . ?

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
C6 H6 O2 0.93 2.65 3.464(2) 146.8 2_666

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.028

_shelxl_version_number           2013-4



