# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_20190701ZH_NGD_XPZ_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc23268p
_database_code_depnum_ccdc_archive 'CCDC 1938531'
loop_
_audit_author_name
_audit_author_address
syna
;Nanjing Tech University
China
;
_audit_update_record             
;
2019-07-05 deposited with the CCDC.	2019-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 O3'
_chemical_formula_weight         346.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.2617(4)
_cell_length_b                   17.7294(9)
_cell_length_c                   11.9398(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.901(2)
_cell_angle_gamma                90
_cell_volume                     1925.19(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    5402
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.991
_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      193(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            14179
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.082
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_full        25.009
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3364
_reflns_number_gt                2687
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+2.0000P] 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         3364
_refine_ls_number_parameters     253
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.1218
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.024
_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
C1 C 0.4563(3) 0.32838(15) 0.7633(2) 0.0530(6) Uani 1 1 d . . . . .
H1A H 0.491664 0.286301 0.727192 0.064 Uiso 1 1 calc R U . . .
C2 C 0.4907(3) 0.33540(18) 0.8800(2) 0.0659(8) Uani 1 1 d . . . . .
H2A H 0.549709 0.298165 0.924084 0.079 Uiso 1 1 calc R U . . .
C3 C 0.4404(3) 0.3957(2) 0.9331(2) 0.0710(8) Uani 1 1 d . . . . .
H3A H 0.464093 0.400191 1.013832 0.085 Uiso 1 1 calc R U . . .
C4 C 0.3555(3) 0.44983(18) 0.8694(2) 0.0656(8) Uani 1 1 d . . . . .
H4A H 0.320928 0.491801 0.906235 0.079 Uiso 1 1 calc R U . . .
C5 C 0.3203(3) 0.44340(15) 0.7521(2) 0.0529(6) Uani 1 1 d . . . . .
H5A H 0.261645 0.480925 0.708409 0.063 Uiso 1 1 calc R U . . .
C6 C 0.3705(2) 0.38230(14) 0.69798(19) 0.0431(5) Uani 1 1 d . . . . .
C7 C 0.3339(2) 0.37487(13) 0.5760(2) 0.0452(6) Uani 1 1 d . . . . .
C8 C 0.3032(3) 0.36844(13) 0.4750(2) 0.0446(6) Uani 1 1 d . . . . .
C9 C 0.3628(3) 0.28125(13) 0.2095(2) 0.0512(6) Uani 1 1 d . . . . .
H9A H 0.264626 0.264786 0.182965 0.061 Uiso 1 1 calc R U . . .
C10 C 0.4738(3) 0.25377(15) 0.1586(2) 0.0643(8) Uani 1 1 d . . . . .
H10A H 0.451974 0.218643 0.097691 0.077 Uiso 1 1 calc R U . . .
C11 C 0.6157(4) 0.27711(17) 0.1960(3) 0.0721(9) Uani 1 1 d . . . . .
H11A H 0.692133 0.258153 0.160789 0.086 Uiso 1 1 calc R U . . .
C12 C 0.6482(3) 0.32810(18) 0.2846(3) 0.0739(9) Uani 1 1 d . . . . .
H12A H 0.746637 0.344422 0.310281 0.089 Uiso 1 1 calc R U . . .
C13 C 0.5361(3) 0.35538(15) 0.3361(2) 0.0592(7) Uani 1 1 d . . . . .
H13A H 0.558464 0.390072 0.397540 0.071 Uiso 1 1 calc R U . . .
C14 C 0.3917(3) 0.33243(13) 0.29851(19) 0.0434(5) Uani 1 1 d . . . . .
C15 C 0.2657(2) 0.36333(13) 0.34994(18) 0.0413(5) Uani 1 1 d . . . . .
H15A H 0.181015 0.327718 0.330029 0.050 Uiso 1 1 calc R U . . .
C16 C 0.0780(3) 0.46828(15) 0.3464(2) 0.0495(6) Uani 1 1 d . . . . .
C17 C 0.0945(3) 0.54994(16) 0.3766(3) 0.0677(8) Uani 1 1 d . . . . .
H17A H 0.109398 0.556760 0.460320 0.081 Uiso 1 1 calc R U . . .
H17B H 0.005670 0.578360 0.340766 0.081 Uiso 1 1 calc R U . . .
C18 C 0.2280(3) 0.57719(14) 0.3316(2) 0.0565(7) Uani 1 1 d . . . . .
H18A H 0.281380 0.616582 0.381869 0.068 Uiso 1 1 calc R U . . .
H18B H 0.199041 0.597824 0.253565 0.068 Uiso 1 1 calc R U . . .
C19 C 0.3223(3) 0.50654(13) 0.3318(2) 0.0504(6) Uani 1 1 d . . . . .
H19A H 0.387825 0.511344 0.275631 0.060 Uiso 1 1 calc R U . . .
H19B H 0.383344 0.498100 0.408290 0.060 Uiso 1 1 calc R U . . .
C20 C 0.2142(2) 0.44193(13) 0.29972(18) 0.0406(5) Uani 1 1 d . . . . .
C21 C 0.1697(3) 0.43729(17) 0.1704(2) 0.0590(7) Uani 1 1 d . . . . .
C22 C 0.0381(6) 0.3770(3) 0.0104(4) 0.0748(13) Uani 0.7 1 d . U P A 1
H22A H 0.028057 0.427433 -0.025755 0.090 Uiso 0.7 1 calc R U P A 1
H22B H 0.114141 0.347901 -0.019105 0.090 Uiso 0.7 1 calc R U P A 1
C23 C -0.1044(6) 0.3363(3) -0.0087(4) 0.0875(14) Uani 0.7 1 d . U P A 1
H23A H -0.139272 0.329025 -0.090694 0.131 Uiso 0.7 1 calc R U P A 1
H23B H -0.091397 0.287136 0.029316 0.131 Uiso 0.7 1 calc R U P A 1
H23C H -0.176731 0.365975 0.022725 0.131 Uiso 0.7 1 calc R U P A 1
O1 O -0.02243(19) 0.42784(11) 0.35817(16) 0.0647(5) Uani 1 1 d . . . . .
O2 O 0.2122(3) 0.47835(13) 0.10487(18) 0.0986(8) Uani 1 1 d . . . . .
O3 O 0.0739(2) 0.38295(13) 0.13945(15) 0.0801(7) Uani 1 1 d . . . . .
C23' C 0.0405(12) 0.3195(6) -0.0199(9) 0.071(3) Uani 0.3 1 d . U P A 2
H23D H -0.019878 0.305934 -0.093698 0.107 Uiso 0.3 1 calc R U P A 2
H23E H 0.133350 0.341580 -0.031964 0.107 Uiso 0.3 1 calc R U P A 2
H23F H 0.060913 0.274215 0.027514 0.107 Uiso 0.3 1 calc R U P A 2
C22' C -0.0321(16) 0.3700(8) 0.0329(11) 0.088(4) Uani 0.3 1 d . U P A 2
H22C H -0.125681 0.348958 0.047829 0.106 Uiso 0.3 1 calc R U P A 2
H22D H -0.052575 0.416946 -0.012198 0.106 Uiso 0.3 1 calc R U P A 2


_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 1.385(3) . ?
C1 C2 1.376(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.369(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.375(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.382(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.386(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.438(3) . ?
C7 C8 1.190(3) . ?
C8 C15 1.471(3) . ?
C9 C14 1.385(3) . ?
C9 C10 1.379(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.370(4) . ?
C10 H10A 0.9500 . ?
C11 C12 1.381(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.389(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.389(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.520(3) . ?
C15 C20 1.556(3) . ?
C15 H15A 1.0000 . ?
C16 O1 1.204(3) . ?
C16 C17 1.493(4) . ?
C16 C20 1.544(3) . ?
C17 C18 1.517(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.527(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.522(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.523(3) . ?
C21 O2 1.189(3) . ?
C21 O3 1.314(3) . ?
C22 C23 1.483(7) . ?
C22 O3 1.517(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O3 C22' 1.471(13) . ?
C23' C22' 1.346(16) . ?
C23' H23D 0.9800 . ?
C23' H23E 0.9800 . ?
C23' H23F 0.9800 . ?
C22' H22C 0.9900 . ?
C22' H22D 0.9900 . ?

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 120.4(3) . . ?
C6 C1 H1A 119.8 . . ?
C2 C1 H1A 119.8 . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C5 C6 C1 119.0(2) . . ?
C5 C6 C7 120.5(2) . . ?
C1 C6 C7 120.5(2) . . ?
C8 C7 C6 179.7(3) . . ?
C7 C8 C15 178.0(3) . . ?
C14 C9 C10 121.1(3) . . ?
C14 C9 H9A 119.4 . . ?
C10 C9 H9A 119.4 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10A 120.0 . . ?
C9 C10 H10A 120.0 . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H11A 119.9 . . ?
C12 C11 H11A 119.9 . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 H12A 120.2 . . ?
C11 C12 H12A 120.2 . . ?
C12 C13 C14 120.7(3) . . ?
C12 C13 H13A 119.7 . . ?
C14 C13 H13A 119.7 . . ?
C9 C14 C13 118.4(2) . . ?
C9 C14 C15 119.6(2) . . ?
C13 C14 C15 122.0(2) . . ?
C8 C15 C14 112.38(19) . . ?
C8 C15 C20 109.41(18) . . ?
C14 C15 C20 111.73(18) . . ?
C8 C15 H15A 107.7 . . ?
C14 C15 H15A 107.7 . . ?
C20 C15 H15A 107.7 . . ?
O1 C16 C17 126.5(2) . . ?
O1 C16 C20 124.3(2) . . ?
C17 C16 C20 109.1(2) . . ?
C16 C17 C18 106.0(2) . . ?
C16 C17 H17A 110.5 . . ?
C18 C17 H17A 110.5 . . ?
C16 C17 H17B 110.5 . . ?
C18 C17 H17B 110.5 . . ?
H17A C17 H17B 108.7 . . ?
C17 C18 C19 104.0(2) . . ?
C17 C18 H18A 110.9 . . ?
C19 C18 H18A 110.9 . . ?
C17 C18 H18B 110.9 . . ?
C19 C18 H18B 110.9 . . ?
H18A C18 H18B 109.0 . . ?
C20 C19 C18 105.54(19) . . ?
C20 C19 H19A 110.6 . . ?
C18 C19 H19A 110.6 . . ?
C20 C19 H19B 110.6 . . ?
C18 C19 H19B 110.6 . . ?
H19A C19 H19B 108.8 . . ?
C19 C20 C21 109.6(2) . . ?
C19 C20 C16 102.98(19) . . ?
C21 C20 C16 107.42(19) . . ?
C19 C20 C15 115.95(18) . . ?
C21 C20 C15 110.3(2) . . ?
C16 C20 C15 110.10(18) . . ?
O2 C21 O3 123.6(3) . . ?
O2 C21 C20 125.0(3) . . ?
O3 C21 C20 111.3(2) . . ?
C23 C22 O3 102.0(4) . . ?
C23 C22 H22A 111.4 . . ?
O3 C22 H22A 111.4 . . ?
C23 C22 H22B 111.4 . . ?
O3 C22 H22B 111.4 . . ?
H22A C22 H22B 109.2 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 O3 C22' 131.5(6) . . ?
C21 O3 C22 110.0(3) . . ?
C22' C23' H23D 109.5 . . ?
C22' C23' H23E 109.5 . . ?
H23D C23' H23E 109.5 . . ?
C22' C23' H23F 109.5 . . ?
H23D C23' H23F 109.5 . . ?
H23E C23' H23F 109.5 . . ?
C23' C22' O3 101.4(10) . . ?
C23' C22' H22C 111.5 . . ?
O3 C22' H22C 111.5 . . ?
C23' C22' H22D 111.5 . . ?
O3 C22' H22D 111.5 . . ?
H22C C22' H22D 109.3 . . ?

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_20190322ZH_NGD_XXD_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc229b80
_database_code_depnum_ccdc_archive 'CCDC 1915591'
loop_
_audit_author_name
_audit_author_address
a
;Nanjing Tech University
China
;
_audit_update_record             
;
2019-05-13 deposited with the CCDC.	2019-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 O3'
_chemical_formula_weight         346.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   11.3670(7)
_cell_length_b                   15.8302(10)
_cell_length_c                   11.4198(7)
_cell_angle_alpha                90
_cell_angle_beta                 114.025(2)
_cell_angle_gamma                90
_cell_volume                     1876.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9659
_cell_measurement_theta_min      3.70
_cell_measurement_theta_max      53.89

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.406
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.945
_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      193(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12903
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.024
_diffrn_reflns_theta_max         52.983
_diffrn_reflns_theta_full        52.983
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3300
_reflns_number_gt                2992
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0483P)²+0.5020P] 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         3300
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1103
_refine_ls_wR_factor_gt          0.1061
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.76470(14) 0.43038(10) 0.87077(14) 0.0419(3) Uani 1 1 d . . . . .
H1 H 0.788610 0.398247 0.813647 0.050 Uiso 1 1 calc R U . . .
C2 C 0.85456(15) 0.44645(10) 0.99424(15) 0.0462(4) Uani 1 1 d . . . . .
H2 H 0.939453 0.424602 1.021785 0.055 Uiso 1 1 calc R U . . .
C3 C 0.82114(15) 0.49397(10) 1.07706(14) 0.0439(4) Uani 1 1 d . . . . .
H3 H 0.882784 0.504496 1.161768 0.053 Uiso 1 1 calc R U . . .
C4 C 0.69876(15) 0.52614(10) 1.03726(14) 0.0444(4) Uani 1 1 d . . . . .
H4 H 0.676424 0.559698 1.094119 0.053 Uiso 1 1 calc R U . . .
C5 C 0.60753(14) 0.50985(9) 0.91429(13) 0.0394(3) Uani 1 1 d . . . . .
H5 H 0.522909 0.532030 0.887480 0.047 Uiso 1 1 calc R U . . .
C6 C 0.63970(13) 0.46113(8) 0.83026(12) 0.0333(3) Uani 1 1 d . . . . .
C7 C 0.54431(13) 0.44072(9) 0.70434(13) 0.0339(3) Uani 1 1 d . . . . .
C8 C 0.46686(13) 0.42076(8) 0.60071(12) 0.0331(3) Uani 1 1 d . . . . .
C9 C 0.36836(12) 0.39326(8) 0.47619(11) 0.0309(3) Uani 1 1 d . . . . .
H9 H 0.342971 0.443608 0.418311 0.037 Uiso 1 1 calc R U . . .
C10 C 0.41920(12) 0.32649(8) 0.41309(12) 0.0321(3) Uani 1 1 d . . . . .
C11 C 0.51550(13) 0.26997(9) 0.48420(13) 0.0377(3) Uani 1 1 d . . . . .
H11 H 0.552393 0.273474 0.575124 0.045 Uiso 1 1 calc R U . . .
C12 C 0.55823(15) 0.20884(10) 0.42451(14) 0.0436(3) Uani 1 1 d . . . . .
H12 H 0.623709 0.170500 0.474538 0.052 Uiso 1 1 calc R U . . .
C13 C 0.50616(16) 0.20318(10) 0.29226(15) 0.0463(4) Uani 1 1 d . . . . .
H13 H 0.535290 0.160984 0.251178 0.056 Uiso 1 1 calc R U . . .
C14 C 0.41135(16) 0.25947(11) 0.22043(14) 0.0464(4) Uani 1 1 d . . . . .
H14 H 0.375696 0.256119 0.129512 0.056 Uiso 1 1 calc R U . . .
C15 C 0.36783(14) 0.32073(9) 0.27980(12) 0.0388(3) Uani 1 1 d . . . . .
H15 H 0.302568 0.359066 0.229361 0.047 Uiso 1 1 calc R U . . .
C16 C 0.24658(12) 0.36297(8) 0.49556(11) 0.0299(3) Uani 1 1 d . . . . .
C17 C 0.20173(12) 0.43323(9) 0.56003(12) 0.0343(3) Uani 1 1 d . . . . .
C18 C 0.15575(18) 0.57913(11) 0.55686(17) 0.0555(4) Uani 1 1 d . . . . .
H18A H 0.091846 0.561176 0.590303 0.067 Uiso 1 1 calc R U . . .
H18B H 0.114535 0.621767 0.488991 0.067 Uiso 1 1 calc R U . . .
C19 C 0.26884(17) 0.61738(12) 0.66219(19) 0.0595(5) Uani 1 1 d . . . . .
H19A H 0.299863 0.579038 0.735948 0.089 Uiso 1 1 calc R U . . .
H19B H 0.243719 0.671328 0.687381 0.089 Uiso 1 1 calc R U . . .
H19C H 0.337549 0.627021 0.632729 0.089 Uiso 1 1 calc R U . . .
C20 C 0.26021(13) 0.28015(9) 0.56837(13) 0.0367(3) Uani 1 1 d . . . . .
H20A H 0.288814 0.290967 0.661294 0.044 Uiso 1 1 calc R U . . .
H20B H 0.323771 0.242744 0.555554 0.044 Uiso 1 1 calc R U . . .
C21 C 0.12635(15) 0.23963(10) 0.51318(15) 0.0452(4) Uani 1 1 d . . . . .
H21A H 0.132283 0.177582 0.524953 0.054 Uiso 1 1 calc R U . . .
H21B H 0.071797 0.262890 0.554443 0.054 Uiso 1 1 calc R U . . .
C22 C 0.07280(16) 0.26272(11) 0.37182(15) 0.0524(4) Uani 1 1 d . . . . .
H22A H 0.095498 0.218976 0.322599 0.063 Uiso 1 1 calc R U . . .
H22B H -0.022160 0.267915 0.336586 0.063 Uiso 1 1 calc R U . . .
C23 C 0.13263(13) 0.34539(9) 0.36436(12) 0.0367(3) Uani 1 1 d . . . . .
O1 O 0.17370(12) 0.42228(7) 0.64939(10) 0.0528(3) Uani 1 1 d . . . . .
O2 O 0.19436(11) 0.50665(7) 0.50270(10) 0.0487(3) Uani 1 1 d . . . . .
O3 O 0.10093(11) 0.39152(8) 0.27302(9) 0.0536(3) Uani 1 1 d . . . . .


_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 C2 1.387(2) . ?
C1 C6 1.391(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.377(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.4416(18) . ?
C7 C8 1.1946(19) . ?
C8 C9 1.4726(18) . ?
C9 C10 1.5198(18) . ?
C9 C16 1.5634(18) . ?
C9 H9 1.0000 . ?
C10 C11 1.3907(19) . ?
C10 C15 1.3937(18) . ?
C11 C12 1.381(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C20 1.5264(18) . ?
C16 C17 1.5311(18) . ?
C16 C23 1.5555(17) . ?
C17 O1 1.1990(17) . ?
C17 O2 1.3198(17) . ?
C18 O2 1.4535(18) . ?
C18 C19 1.486(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.531(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.520(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.493(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 O3 1.2020(17) . ?

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
C2 C1 C6 120.25(14) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C3 C2 C1 120.23(14) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.04(13) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.30(14) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.19(14) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.97(13) . . ?
C1 C6 C7 120.33(12) . . ?
C5 C6 C7 120.68(13) . . ?
C8 C7 C6 177.55(15) . . ?
C7 C8 C9 177.08(14) . . ?
C8 C9 C10 112.15(11) . . ?
C8 C9 C16 108.84(10) . . ?
C10 C9 C16 112.53(11) . . ?
C8 C9 H9 107.7 . . ?
C10 C9 H9 107.7 . . ?
C16 C9 H9 107.7 . . ?
C11 C10 C15 118.41(12) . . ?
C11 C10 C9 122.10(11) . . ?
C15 C10 C9 119.48(12) . . ?
C12 C11 C10 120.93(13) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 120.30(14) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 119.37(14) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 120.58(13) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 120.40(14) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C20 C16 C17 109.99(11) . . ?
C20 C16 C23 103.36(11) . . ?
C17 C16 C23 106.46(10) . . ?
C20 C16 C9 116.18(10) . . ?
C17 C16 C9 109.42(10) . . ?
C23 C16 C9 110.89(10) . . ?
O1 C17 O2 124.35(13) . . ?
O1 C17 C16 124.07(13) . . ?
O2 C17 C16 111.56(11) . . ?
O2 C18 C19 110.77(14) . . ?
O2 C18 H18A 109.5 . . ?
C19 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
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 . . ?
C16 C20 C21 105.79(11) . . ?
C16 C20 H20A 110.6 . . ?
C21 C20 H20A 110.6 . . ?
C16 C20 H20B 110.6 . . ?
C21 C20 H20B 110.6 . . ?
H20A C20 H20B 108.7 . . ?
C22 C21 C20 103.75(12) . . ?
C22 C21 H21A 111.0 . . ?
C20 C21 H21A 111.0 . . ?
C22 C21 H21B 111.0 . . ?
C20 C21 H21B 111.0 . . ?
H21A C21 H21B 109.0 . . ?
C23 C22 C21 106.06(12) . . ?
C23 C22 H22A 110.5 . . ?
C21 C22 H22A 110.5 . . ?
C23 C22 H22B 110.5 . . ?
C21 C22 H22B 110.5 . . ?
H22A C22 H22B 108.7 . . ?
O3 C23 C22 126.82(13) . . ?
O3 C23 C16 124.40(13) . . ?
C22 C23 C16 108.77(12) . . ?
C17 O2 C18 116.95(12) . . ?

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.033

