# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_20171017cz971_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1922985'
loop_
_audit_author_name
_audit_author_address
'Jiangtao Sun'
;Changzhou University
China
;
_audit_update_record             
;
2019-06-14 deposited with the CCDC.	2019-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 O3'
_chemical_formula_weight         344.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   22.150(2)
_cell_length_b                   6.9258(9)
_cell_length_c                   24.121(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.162(4)
_cell_angle_gamma                90
_cell_volume                     3535.5(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    4574
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      27.55
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             1456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(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            12075
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.196
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.009
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3117
_reflns_number_gt                2485
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0805P)²+1.9003P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3117
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1423
_refine_ls_wR_factor_gt          0.1305
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
C1 C 0.58265(9) 0.7765(3) 0.70640(8) 0.0280(5) Uani 1 1 d . . . . .
C2 C 0.60018(11) 0.8719(3) 0.75937(9) 0.0354(5) Uani 1 1 d . . . . .
H2 H 0.579757 0.846713 0.788161 0.042 Uiso 1 1 calc R U . . .
C3 C 0.64868(10) 1.0053(3) 0.76846(9) 0.0354(5) Uani 1 1 d . . . . .
H3A H 0.661860 1.072954 0.804281 0.042 Uiso 1 1 calc R U . . .
C4 C 0.67843(10) 1.0422(3) 0.72646(9) 0.0368(5) Uani 1 1 d . . . . .
H4 H 0.711875 1.133547 0.733884 0.044 Uiso 1 1 calc R U . . .
C5 C 0.65958(9) 0.9464(3) 0.67354(9) 0.0305(5) Uani 1 1 d . . . . .
H5 H 0.679617 0.972055 0.644506 0.037 Uiso 1 1 calc R U . . .
C6 C 0.61118(8) 0.8131(3) 0.66389(7) 0.0214(4) Uani 1 1 d . . . . .
C7 C 0.57926(8) 0.6919(3) 0.61080(7) 0.0199(4) Uani 1 1 d . . . . .
C8 C 0.68041(9) 0.4979(3) 0.62852(9) 0.0262(4) Uani 1 1 d . . . . .
H8 H 0.691963 0.539879 0.667744 0.031 Uiso 1 1 calc R U . . .
C9 C 0.71912(9) 0.3705(3) 0.61059(10) 0.0327(5) Uani 1 1 d . . . . .
H9 H 0.756794 0.324662 0.637684 0.039 Uiso 1 1 calc R U . . .
C10 C 0.70326(10) 0.3097(3) 0.55344(10) 0.0340(5) Uani 1 1 d . . . . .
H10 H 0.729792 0.221921 0.541309 0.041 Uiso 1 1 calc R U . . .
C11 C 0.64880(10) 0.3773(3) 0.51432(9) 0.0329(5) Uani 1 1 d . . . . .
H11 H 0.637990 0.337288 0.474936 0.039 Uiso 1 1 calc R U . . .
C12 C 0.60952(9) 0.5040(3) 0.53220(8) 0.0263(4) Uani 1 1 d . . . . .
H12 H 0.571906 0.549445 0.504923 0.032 Uiso 1 1 calc R U . . .
C13 C 0.62477(8) 0.5647(3) 0.58952(8) 0.0205(4) Uani 1 1 d . . . . .
C14 C 0.54448(8) 0.8285(3) 0.56182(7) 0.0198(4) Uani 1 1 d . . . . .
C15 C 0.53043(8) 0.5716(3) 0.63309(7) 0.0213(4) Uani 1 1 d . . . . .
H15 H 0.486899 0.601223 0.607598 0.026 Uiso 1 1 calc R U . . .
C16 C 0.53910(9) 0.3560(3) 0.63526(10) 0.0322(5) Uani 1 1 d . . . . .
H16A H 0.583830 0.326520 0.655896 0.039 Uiso 1 1 calc R U . . .
H16B H 0.530161 0.306846 0.595099 0.039 Uiso 1 1 calc R U . . .
C17 C 0.49695(9) 0.2482(3) 0.66526(10) 0.0369(5) Uani 1 1 d . . . . .
H17A H 0.506376 0.108478 0.665136 0.044 Uiso 1 1 calc R U . . .
H17B H 0.508358 0.290445 0.706263 0.044 Uiso 1 1 calc R U . . .
C18 C 0.42713(9) 0.2761(3) 0.63865(8) 0.0261(4) Uani 1 1 d . . . . .
C19 C 0.39430(10) 0.4135(3) 0.65945(9) 0.0333(5) Uani 1 1 d . . . . .
H19 H 0.416404 0.494441 0.690632 0.040 Uiso 1 1 calc R U . . .
C20 C 0.32993(11) 0.4354(4) 0.63576(13) 0.0508(7) Uani 1 1 d . . . . .
H20 H 0.308252 0.530650 0.650903 0.061 Uiso 1 1 calc R U . . .
C21 C 0.29706(12) 0.3215(5) 0.59073(13) 0.0608(9) Uani 1 1 d . . . . .
H21 H 0.252701 0.336916 0.574612 0.073 Uiso 1 1 calc R U . . .
C22 C 0.32855(14) 0.1853(5) 0.56913(11) 0.0598(8) Uani 1 1 d . . . . .
H22 H 0.305940 0.106195 0.537656 0.072 Uiso 1 1 calc R U . . .
C23 C 0.39307(12) 0.1612(3) 0.59263(10) 0.0433(6) Uani 1 1 d . . . . .
H23 H 0.414344 0.065526 0.577244 0.052 Uiso 1 1 calc R U . . .
O1 O 0.53590(8) 0.6417(2) 0.69121(6) 0.0454(5) Uani 1 1 d . . . . .
O2 O 0.48753(6) 0.8294(2) 0.54063(6) 0.0320(4) Uani 1 1 d . . . . .
O3 O 0.58247(6) 0.9465(2) 0.54576(6) 0.0301(4) Uani 1 1 d . . . . .
H3 H 0.561132 1.021152 0.519905 0.045 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
C1 O1 1.361(2) . ?
C1 C6 1.377(3) . ?
C1 C2 1.388(3) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.520(2) . ?
C7 C13 1.537(2) . ?
C7 C14 1.532(2) . ?
C7 C15 1.580(2) . ?
C8 C9 1.385(3) . ?
C8 C13 1.391(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(3) . ?
C12 H12 0.9500 . ?
C14 O2 1.213(2) . ?
C14 O3 1.311(2) . ?
C15 O1 1.455(2) . ?
C15 C16 1.504(3) . ?
C15 H15 1.0000 . ?
C16 C17 1.534(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.502(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.379(3) . ?
C18 C23 1.393(3) . ?
C19 C20 1.379(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.366(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.365(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.383(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
O3 H3 0.8400 . ?

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
O1 C1 C6 113.92(17) . . ?
O1 C1 C2 123.91(19) . . ?
C6 C1 C2 122.2(2) . . ?
C3 C2 C1 117.2(2) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C4 C3 C2 121.44(19) . . ?
C4 C3 H3A 119.3 . . ?
C2 C3 H3A 119.3 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 118.8(2) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C1 C6 C5 120.08(18) . . ?
C1 C6 C7 108.91(16) . . ?
C5 C6 C7 130.99(17) . . ?
C6 C7 C13 114.21(14) . . ?
C6 C7 C14 108.17(15) . . ?
C13 C7 C14 109.07(14) . . ?
C6 C7 C15 101.50(14) . . ?
C13 C7 C15 113.18(15) . . ?
C14 C7 C15 110.44(14) . . ?
C9 C8 C13 120.49(18) . . ?
C9 C8 H8 119.8 . . ?
C13 C8 H8 119.8 . . ?
C10 C9 C8 120.40(19) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 119.56(18) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.27(19) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.61(18) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C8 118.67(17) . . ?
C12 C13 C7 121.03(16) . . ?
C8 C13 C7 120.18(16) . . ?
O2 C14 O3 123.44(16) . . ?
O2 C14 C7 123.46(16) . . ?
O3 C14 C7 113.09(14) . . ?
O1 C15 C16 108.94(16) . . ?
O1 C15 C7 106.33(14) . . ?
C16 C15 C7 116.24(14) . . ?
O1 C15 H15 108.4 . . ?
C16 C15 H15 108.4 . . ?
C7 C15 H15 108.4 . . ?
C15 C16 C17 114.23(16) . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C18 C17 C16 115.41(17) . . ?
C18 C17 H17A 108.4 . . ?
C16 C17 H17A 108.4 . . ?
C18 C17 H17B 108.4 . . ?
C16 C17 H17B 108.4 . . ?
H17A C17 H17B 107.5 . . ?
C19 C18 C23 117.7(2) . . ?
C19 C18 C17 121.36(19) . . ?
C23 C18 C17 121.0(2) . . ?
C20 C19 C18 121.1(2) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C21 C20 C19 120.6(3) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 119.4(2) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C23 120.6(2) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C18 120.6(2) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
C1 O1 C15 109.19(14) . . ?
C14 O3 H3 109.5 . . ?

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 1923042'
loop_
_audit_author_name
_audit_author_address
'Jiangtao Sun'
;Changzhou University
China
;
_audit_update_record             
;
2019-06-14 deposited with the CCDC.	2019-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 O3'
_chemical_formula_weight         344.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   18.0338(16)
_cell_length_b                   5.8228(6)
_cell_length_c                   17.2022(17)
_cell_angle_alpha                90
_cell_angle_beta                 99.630(3)
_cell_angle_gamma                90
_cell_volume                     1780.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    5471
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      27.87
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(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            12158
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.291
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_full        25.007
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3126
_reflns_number_gt                2628
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0531P)²+0.8601P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3126
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1184
_refine_ls_wR_factor_gt          0.1122
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
C1 C 0.75229(9) 0.7023(3) 0.44439(9) 0.0221(4) Uani 1 1 d . . . . .
C2 C 0.70309(9) 0.6452(3) 0.49553(10) 0.0278(4) Uani 1 1 d . . . . .
H2 H 0.678317 0.500638 0.491771 0.033 Uiso 1 1 calc R U . . .
C3 C 0.69097(10) 0.8048(4) 0.55240(10) 0.0328(5) Uani 1 1 d . . . . .
H3A H 0.657682 0.768131 0.587938 0.039 Uiso 1 1 calc R U . . .
C4 C 0.72658(10) 1.0153(4) 0.55788(10) 0.0321(4) Uani 1 1 d . . . . .
H4 H 0.716981 1.121292 0.596978 0.038 Uiso 1 1 calc R U . . .
C5 C 0.77635(10) 1.0761(3) 0.50742(10) 0.0279(4) Uani 1 1 d . . . . .
H5 H 0.801446 1.220173 0.511355 0.034 Uiso 1 1 calc R U . . .
C6 C 0.78709(9) 0.9147(3) 0.45124(9) 0.0241(4) Uani 1 1 d . . . . .
C7 C 0.84979(9) 0.7185(3) 0.37026(9) 0.0209(4) Uani 1 1 d . . . . .
C8 C 0.91709(9) 0.6251(3) 0.42906(9) 0.0209(4) Uani 1 1 d . . . . .
C9 C 0.60264(10) 0.1912(3) 0.18468(11) 0.0311(4) Uani 1 1 d . . . . .
H9 H 0.638907 0.075561 0.201640 0.037 Uiso 1 1 calc R U . . .
C10 C 0.55330(11) 0.1629(4) 0.11423(11) 0.0368(5) Uani 1 1 d . . . . .
H10 H 0.555927 0.028596 0.083474 0.044 Uiso 1 1 calc R U . . .
C11 C 0.50041(10) 0.3299(4) 0.08882(11) 0.0359(5) Uani 1 1 d . . . . .
H11 H 0.466450 0.310858 0.040725 0.043 Uiso 1 1 calc R U . . .
C12 C 0.49727(10) 0.5246(4) 0.13382(11) 0.0348(5) Uani 1 1 d . . . . .
H12 H 0.461188 0.640466 0.116509 0.042 Uiso 1 1 calc R U . . .
C13 C 0.54685(10) 0.5520(3) 0.20460(11) 0.0303(4) Uani 1 1 d . . . . .
H13 H 0.544228 0.686496 0.235262 0.036 Uiso 1 1 calc R U . . .
C14 C 0.59985(9) 0.3852(3) 0.23063(10) 0.0257(4) Uani 1 1 d . . . . .
C15 C 0.65295(10) 0.4155(4) 0.30771(10) 0.0317(4) Uani 1 1 d . . . . .
H15A H 0.671908 0.262989 0.327297 0.038 Uiso 1 1 calc R U . . .
H15B H 0.624957 0.482224 0.347127 0.038 Uiso 1 1 calc R U . . .
C16 C 0.71992(9) 0.5708(3) 0.30015(10) 0.0251(4) Uani 1 1 d . . . . .
H16A H 0.701600 0.728863 0.287461 0.030 Uiso 1 1 calc R U . . .
H16B H 0.744177 0.515517 0.256091 0.030 Uiso 1 1 calc R U . . .
C17 C 0.77837(9) 0.5750(3) 0.37619(9) 0.0219(4) Uani 1 1 d . . . . .
H17 H 0.793092 0.414392 0.392646 0.026 Uiso 1 1 calc R U . . .
C18 C 0.91128(10) 0.5505(4) 0.26270(10) 0.0309(4) Uani 1 1 d . . . . .
H18 H 0.923357 0.419551 0.295292 0.037 Uiso 1 1 calc R U . . .
C19 C 0.93232(11) 0.5587(4) 0.18863(11) 0.0414(5) Uani 1 1 d . . . . .
H19 H 0.959113 0.433988 0.170941 0.050 Uiso 1 1 calc R U . . .
C20 C 0.91464(12) 0.7450(5) 0.14137(11) 0.0478(6) Uani 1 1 d . . . . .
H20 H 0.929203 0.750076 0.090815 0.057 Uiso 1 1 calc R U . . .
C21 C 0.87581(13) 0.9257(4) 0.16652(11) 0.0467(6) Uani 1 1 d . . . . .
H21 H 0.863178 1.054261 0.132904 0.056 Uiso 1 1 calc R U . . .
C22 C 0.85463(11) 0.9224(4) 0.24120(11) 0.0345(5) Uani 1 1 d . . . . .
H22 H 0.828253 1.048459 0.258615 0.041 Uiso 1 1 calc R U . . .
C23 C 0.87265(9) 0.7331(3) 0.28931(9) 0.0234(4) Uani 1 1 d . . . . .
O1 O 0.83497(6) 0.9478(2) 0.39717(7) 0.0255(3) Uani 1 1 d . . . . .
O2 O 0.91788(7) 0.4315(2) 0.45630(7) 0.0302(3) Uani 1 1 d . . . . .
O3 O 0.97205(7) 0.7723(2) 0.44547(7) 0.0306(3) Uani 1 1 d . . . . .
H3 H 1.007759 0.711495 0.476182 0.046 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
C1 C6 1.383(3) . ?
C1 C2 1.390(2) . ?
C1 C17 1.527(2) . ?
C2 C3 1.393(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.395(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(2) . ?
C5 H5 0.9500 . ?
C6 O1 1.3843(19) . ?
C7 O1 1.453(2) . ?
C7 C23 1.519(2) . ?
C7 C8 1.543(2) . ?
C7 C17 1.553(2) . ?
C8 O2 1.220(2) . ?
C8 O3 1.305(2) . ?
C9 C14 1.384(3) . ?
C9 C10 1.388(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.394(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.511(2) . ?
C15 C16 1.532(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.537(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17 1.0000 . ?
C18 C23 1.390(3) . ?
C18 C19 1.390(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.361(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.373(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.400(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.384(3) . ?
C22 H22 0.9500 . ?
O3 H3 0.8400 . ?

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
C6 C1 C2 119.26(16) . . ?
C6 C1 C17 107.81(14) . . ?
C2 C1 C17 132.93(16) . . ?
C1 C2 C3 118.46(18) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 120.98(17) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 . . ?
C3 C4 C5 121.59(17) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 116.19(18) . . ?
C6 C5 H5 121.9 . . ?
C4 C5 H5 121.9 . . ?
C1 C6 C5 123.51(16) . . ?
C1 C6 O1 113.11(15) . . ?
C5 C6 O1 123.37(16) . . ?
O1 C7 C23 109.47(14) . . ?
O1 C7 C8 106.35(13) . . ?
C23 C7 C8 108.44(13) . . ?
O1 C7 C17 105.95(12) . . ?
C23 C7 C17 116.45(13) . . ?
C8 C7 C17 109.72(13) . . ?
O2 C8 O3 124.37(15) . . ?
O2 C8 C7 122.33(15) . . ?
O3 C8 C7 113.30(15) . . ?
C14 C9 C10 121.07(18) . . ?
C14 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 120.05(19) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.48(17) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C13 120.24(18) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.65(18) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C9 118.50(16) . . ?
C13 C14 C15 120.28(17) . . ?
C9 C14 C15 121.22(17) . . ?
C14 C15 C16 112.80(14) . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 C17 112.05(14) . . ?
C15 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C1 C17 C16 113.97(13) . . ?
C1 C17 C7 98.90(13) . . ?
C16 C17 C7 114.27(13) . . ?
C1 C17 H17 109.7 . . ?
C16 C17 H17 109.7 . . ?
C7 C17 H17 109.7 . . ?
C23 C18 C19 120.30(19) . . ?
C23 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 120.1(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.22(18) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C22 120.7(2) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 119.1(2) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 C18 119.52(16) . . ?
C22 C23 C7 121.34(16) . . ?
C18 C23 C7 119.14(16) . . ?
C6 O1 C7 104.76(12) . . ?
C8 O3 H3 109.5 . . ?

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.042

