# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_1183
_database_code_depnum_ccdc_archive 'CCDC 2050867'
loop_
_audit_author_name
_audit_author_address
'xiaoli zhao'
;East China Normal University
China
;
_audit_update_record             
;
2020-12-27 deposited with the CCDC.	2021-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 O4'
_chemical_formula_weight         348.38

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                   8.97980(10)
_cell_length_b                   11.03890(10)
_cell_length_c                   17.28090(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1713.01(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.749
_shelx_estimated_absorpt_T_min   0.744
_shelx_estimated_absorpt_T_max   0.853
_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      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37913
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.754
_diffrn_reflns_theta_max         67.033
_diffrn_reflns_theta_full        67.033
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3043
_reflns_number_gt                3023
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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-2017/1 (Sheldrick, 2017)'
_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)+(0.0345P)²+0.3111P] 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_abs_structure_details 
;
 Flack x determined using 1259 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3043
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.0641
_refine_ls_wR_factor_gt          0.0640
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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 0.65514(13) 0.75260(11) 0.05402(6) 0.0214(3) Uani 1 1 d . . . . .
O2 O 0.92602(13) 0.70981(12) 0.14608(7) 0.0244(3) Uani 1 1 d . . . . .
O3 O 0.55111(14) 0.62389(11) 0.51838(6) 0.0237(3) Uani 1 1 d . . . . .
O4 O 1.11532(13) 0.57058(12) 0.39183(7) 0.0264(3) Uani 1 1 d . . . . .
C1 C 0.50659(19) 0.77384(16) 0.03989(9) 0.0219(4) Uani 1 1 d . . . . .
H1 H 0.463864 0.774038 -0.009134 0.026 Uiso 1 1 calc R U . . .
C2 C 0.43004(19) 0.79451(15) 0.10647(9) 0.0202(3) Uani 1 1 d . . . . .
C3 C 0.26652(19) 0.80634(16) 0.12484(9) 0.0219(4) Uani 1 1 d . . . . .
H3A H 0.216672 0.730221 0.114092 0.026 Uiso 1 1 calc R U . . .
H3B H 0.222613 0.868165 0.092117 0.026 Uiso 1 1 calc R U . . .
C4 C 0.24368(19) 0.84048(16) 0.21061(9) 0.0215(4) Uani 1 1 d . . . . .
H4A H 0.257363 0.927189 0.216262 0.026 Uiso 1 1 calc R U . . .
H4B H 0.141855 0.821827 0.225067 0.026 Uiso 1 1 calc R U . . .
C5 C 0.34973(18) 0.77505(15) 0.26679(9) 0.0185(3) Uani 1 1 d . . . . .
H5A H 0.336506 0.688199 0.261750 0.022 Uiso 1 1 calc R U . . .
H5B H 0.325016 0.797476 0.319526 0.022 Uiso 1 1 calc R U . . .
C6 C 0.51376(19) 0.80768(14) 0.25042(9) 0.0174(3) Uani 1 1 d . . . . .
C7 C 0.63131(18) 0.73640(14) 0.29497(9) 0.0166(3) Uani 1 1 d . . . . .
C8 C 0.60832(18) 0.70362(14) 0.37081(9) 0.0179(3) Uani 1 1 d . . . . .
H8 H 0.516375 0.719194 0.393489 0.022 Uiso 1 1 calc R U . . .
C9 C 0.72084(19) 0.64681(14) 0.41532(9) 0.0185(3) Uani 1 1 d . . . . .
C10 C 0.69384(19) 0.60679(15) 0.49285(9) 0.0193(4) Uani 1 1 d . . . . .
C11 C 0.8066(2) 0.55531(16) 0.53455(9) 0.0218(4) Uani 1 1 d . . . . .
H11 H 0.788192 0.528003 0.584556 0.026 Uiso 1 1 calc R U . . .
C12 C 0.9517(2) 0.54292(16) 0.50253(9) 0.0221(4) Uani 1 1 d . . . . .
H12 H 1.027828 0.510170 0.532390 0.026 Uiso 1 1 calc R U . . .
C13 C 0.98022(19) 0.57872(16) 0.42824(9) 0.0213(4) Uani 1 1 d . . . . .
C14 C 0.86382(19) 0.62927(15) 0.38222(10) 0.0186(3) Uani 1 1 d . . . . .
C15 C 0.88541(19) 0.66081(15) 0.30404(10) 0.0193(3) Uani 1 1 d . . . . .
H15 H 0.977892 0.647313 0.281408 0.023 Uiso 1 1 calc R U . . .
C16 C 0.77339(19) 0.71101(14) 0.26031(9) 0.0182(3) Uani 1 1 d . . . . .
C17 C 0.80345(19) 0.72851(15) 0.17508(9) 0.0189(3) Uani 1 1 d . . . . .
C18 C 0.67079(19) 0.76008(16) 0.13290(9) 0.0190(3) Uani 1 1 d . . . . .
C19 C 0.53813(19) 0.78762(15) 0.16592(9) 0.0180(3) Uani 1 1 d . . . . .
C20 C 0.5441(2) 0.94317(15) 0.26882(9) 0.0223(4) Uani 1 1 d . . . . .
H20A H 0.481478 0.993120 0.237052 0.033 Uiso 1 1 calc R U . . .
H20B H 0.646642 0.961540 0.258421 0.033 Uiso 1 1 calc R U . . .
H20C H 0.522880 0.958582 0.322375 0.033 Uiso 1 1 calc R U . . .
C21 C 0.5161(2) 0.58179(17) 0.59414(10) 0.0253(4) Uani 1 1 d . . . . .
H21A H 0.534621 0.496268 0.597193 0.038 Uiso 1 1 calc R U . . .
H21B H 0.413072 0.597473 0.604989 0.038 Uiso 1 1 calc R U . . .
H21C H 0.577122 0.623248 0.631287 0.038 Uiso 1 1 calc R U . . .
C22 C 1.2412(2) 0.54688(18) 0.43954(10) 0.0288(4) Uani 1 1 d . . . . .
H22A H 1.329736 0.546515 0.408370 0.043 Uiso 1 1 calc R U . . .
H22B H 1.229686 0.469412 0.464055 0.043 Uiso 1 1 calc R U . . .
H22C H 1.249232 0.608743 0.478366 0.043 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 C18 1.3728(18) . ?
O1 C1 1.376(2) . ?
O2 C17 1.227(2) . ?
O3 C10 1.369(2) . ?
O3 C21 1.424(2) . ?
O4 C13 1.370(2) . ?
O4 C22 1.424(2) . ?
C1 C2 1.360(2) . ?
C1 H1 0.9300 . ?
C2 C19 1.415(2) . ?
C2 C3 1.508(2) . ?
C3 C4 1.543(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.540(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.543(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C19 1.493(2) . ?
C6 C7 1.525(2) . ?
C6 C20 1.553(2) . ?
C7 C8 1.375(2) . ?
C7 C16 1.437(2) . ?
C8 C9 1.416(2) . ?
C8 H8 0.9300 . ?
C9 C14 1.419(2) . ?
C9 C10 1.431(2) . ?
C10 C11 1.367(2) . ?
C11 C12 1.422(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.367(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.427(2) . ?
C14 C15 1.408(2) . ?
C15 C16 1.375(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.510(2) . ?
C17 C18 1.439(2) . ?
C18 C19 1.355(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O1 C1 105.37(12) . . ?
C10 O3 C21 117.25(13) . . ?
C13 O4 C22 116.72(13) . . ?
C2 C1 O1 111.62(14) . . ?
C2 C1 H1 124.2 . . ?
O1 C1 H1 124.2 . . ?
C1 C2 C19 104.98(15) . . ?
C1 C2 C3 133.23(15) . . ?
C19 C2 C3 121.31(15) . . ?
C2 C3 C4 110.65(14) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 114.14(14) . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C4 C5 C6 111.43(13) . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C19 C6 C7 108.40(13) . . ?
C19 C6 C5 106.55(13) . . ?
C7 C6 C5 116.60(13) . . ?
C19 C6 C20 108.51(13) . . ?
C7 C6 C20 105.79(13) . . ?
C5 C6 C20 110.78(13) . . ?
C8 C7 C16 118.63(14) . . ?
C8 C7 C6 120.86(15) . . ?
C16 C7 C6 120.32(13) . . ?
C7 C8 C9 121.81(15) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C8 C9 C14 119.14(14) . . ?
C8 C9 C10 121.62(16) . . ?
C14 C9 C10 119.25(15) . . ?
C11 C10 O3 125.53(15) . . ?
C11 C10 C9 119.77(16) . . ?
O3 C10 C9 114.70(14) . . ?
C10 C11 C12 120.90(15) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 120.62(16) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 O4 125.34(15) . . ?
C12 C13 C14 119.92(16) . . ?
O4 C13 C14 114.73(14) . . ?
C15 C14 C9 118.53(15) . . ?
C15 C14 C13 122.03(16) . . ?
C9 C14 C13 119.43(14) . . ?
C16 C15 C14 121.74(16) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C7 119.94(14) . . ?
C15 C16 C17 117.19(15) . . ?
C7 C16 C17 122.71(14) . . ?
O2 C17 C18 125.20(14) . . ?
O2 C17 C16 122.50(15) . . ?
C18 C17 C16 112.15(14) . . ?
C19 C18 O1 109.98(14) . . ?
C19 C18 C17 124.64(14) . . ?
O1 C18 C17 124.95(14) . . ?
C18 C19 C2 108.01(14) . . ?
C18 C19 C6 125.03(14) . . ?
C2 C19 C6 126.96(15) . . ?
C6 C20 H20A 109.5 . . ?
C6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         0.131
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.030



####################################################################### 
# 
# 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_ta_a
_database_code_depnum_ccdc_archive 'CCDC 2050869'
loop_
_audit_author_name
_audit_author_address
'xiaoli zhao'
;East China Normal University
China
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-02-19 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         'C22 H20 O4'
_chemical_formula_sum            'C22 H20 O4'
_chemical_formula_weight         348.38

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                   9.1038(3)
_cell_length_b                   11.1728(4)
_cell_length_c                   17.3015(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1759.82(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9691
_cell_measurement_theta_min      3.96
_cell_measurement_theta_max      68.14

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   0.6811
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.729
_shelx_estimated_absorpt_T_min   0.868
_shelx_estimated_absorpt_T_max   0.868
_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      295(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            24351
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.711
_diffrn_reflns_theta_max         68.224
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3197
_reflns_number_gt                3126
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.996

_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-2016/6 (Sheldrick, 2016)'
_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)+(0.0603P)²+0.1116P] 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_abs_structure_details 
;
 Flack x determined using 1309 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         3197
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0850
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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 0.36132(14) 0.75438(13) 0.05529(7) 0.0553(3) Uani 1 1 d . . . . .
C1 C 0.5077(2) 0.77356(19) 0.04144(10) 0.0563(5) Uani 1 1 d . . . . .
H1 H 0.549574 0.774356 -0.007585 0.068 Uiso 1 1 calc R U . . .
O2 O 0.09537(15) 0.70982(16) 0.14677(8) 0.0644(4) Uani 1 1 d . . . . .
C2 C 0.5841(2) 0.79123(17) 0.10765(10) 0.0499(4) Uani 1 1 d . . . . .
O4 O -0.09333(16) 0.57381(16) 0.39233(9) 0.0678(4) Uani 1 1 d . . . . .
C4 C 0.7703(2) 0.8306(2) 0.21137(11) 0.0576(5) Uani 1 1 d . . . . .
H4A H 0.760623 0.916429 0.218132 0.069 Uiso 1 1 calc R U . . .
H4B H 0.870104 0.808888 0.225106 0.069 Uiso 1 1 calc R U . . .
O3 O 0.46378(16) 0.61870(14) 0.51808(7) 0.0614(4) Uani 1 1 d . . . . .
C3 C 0.7451(2) 0.8003(2) 0.12580(11) 0.0591(5) Uani 1 1 d . . . . .
H3A H 0.789190 0.861851 0.093797 0.071 Uiso 1 1 calc R U . . .
H3B H 0.792652 0.724846 0.113767 0.071 Uiso 1 1 calc R U . . .
C5 C 0.66378(19) 0.76730(17) 0.26726(10) 0.0490(4) Uani 1 1 d . . . . .
H5A H 0.674376 0.681329 0.261764 0.059 Uiso 1 1 calc R U . . .
H5B H 0.688991 0.788303 0.320012 0.059 Uiso 1 1 calc R U . . .
C6 C 0.50300(19) 0.80256(14) 0.25141(9) 0.0426(4) Uani 1 1 d . . . . .
C7 C 0.4778(2) 0.78458(15) 0.16711(9) 0.0438(4) Uani 1 1 d . . . . .
C8 C 0.3469(2) 0.75982(17) 0.13400(10) 0.0466(4) Uani 1 1 d . . . . .
C9 C 0.21590(19) 0.72789(16) 0.17603(10) 0.0468(4) Uani 1 1 d . . . . .
C10 C 0.24547(18) 0.70978(15) 0.26108(9) 0.0431(4) Uani 1 1 d . . . . .
C11 C 0.38563(18) 0.73321(14) 0.29583(9) 0.0407(3) Uani 1 1 d . . . . .
C12 C 0.40765(19) 0.70051(16) 0.37113(9) 0.0440(4) Uani 1 1 d . . . . .
H12 H 0.498557 0.715237 0.393732 0.053 Uiso 1 1 calc R U . . .
C13 C 0.29646(19) 0.64493(15) 0.41580(10) 0.0440(4) Uani 1 1 d . . . . .
C14 C 0.15504(19) 0.62969(15) 0.38259(10) 0.0456(4) Uani 1 1 d . . . . .
C15 C 0.13407(19) 0.66114(16) 0.30482(10) 0.0459(4) Uani 1 1 d . . . . .
H15 H 0.042599 0.648802 0.282253 0.055 Uiso 1 1 calc R U . . .
C16 C 0.0390(2) 0.58023(18) 0.42858(11) 0.0524(4) Uani 1 1 d . . . . .
C17 C 0.0680(2) 0.54369(18) 0.50221(12) 0.0562(5) Uani 1 1 d . . . . .
H17 H -0.007187 0.511367 0.532050 0.067 Uiso 1 1 calc R U . . .
C18 C 0.2105(2) 0.55423(18) 0.53385(11) 0.0549(5) Uani 1 1 d . . . . .
H18 H 0.228152 0.526512 0.583673 0.066 Uiso 1 1 calc R U . . .
C19 C 0.3226(2) 0.60418(17) 0.49281(10) 0.0488(4) Uani 1 1 d . . . . .
C20 C 0.4769(3) 0.93652(16) 0.27065(11) 0.0573(5) Uani 1 1 d . . . . .
H20A H 0.539208 0.985242 0.238812 0.086 Uiso 1 1 calc R U . . .
H20B H 0.499324 0.950713 0.324090 0.086 Uiso 1 1 calc R U . . .
H20C H 0.376002 0.956495 0.260961 0.086 Uiso 1 1 calc R U . . .
C21 C 0.4987(3) 0.5784(2) 0.59344(11) 0.0659(5) Uani 1 1 d . . . . .
H21A H 0.482529 0.493644 0.596707 0.099 Uiso 1 1 calc R U . . .
H21B H 0.437436 0.618624 0.630369 0.099 Uiso 1 1 calc R U . . .
H21C H 0.599950 0.595589 0.604363 0.099 Uiso 1 1 calc R U . . .
C22 C -0.2168(3) 0.5422(3) 0.43713(15) 0.0784(7) Uani 1 1 d . . . . .
H22A H -0.303144 0.543595 0.405303 0.118 Uiso 1 1 calc R U . . .
H22B H -0.227914 0.598214 0.478780 0.118 Uiso 1 1 calc R U . . .
H22C H -0.203312 0.463199 0.457792 0.118 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 C8 1.370(2) . ?
O1 C1 1.371(2) . ?
C1 C2 1.355(3) . ?
C1 H1 0.9300 . ?
O2 C9 1.225(2) . ?
C2 C7 1.414(2) . ?
C2 C3 1.502(3) . ?
O4 C16 1.360(2) . ?
O4 C22 1.410(2) . ?
C4 C3 1.536(3) . ?
C4 C5 1.541(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
O3 C19 1.368(2) . ?
O3 C21 1.416(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 C6 1.540(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.490(2) . ?
C6 C11 1.527(2) . ?
C6 C20 1.552(2) . ?
C7 C8 1.351(3) . ?
C8 C9 1.441(2) . ?
C9 C10 1.510(2) . ?
C10 C15 1.377(2) . ?
C10 C11 1.435(2) . ?
C11 C12 1.368(2) . ?
C12 C13 1.417(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.420(2) . ?
C13 C19 1.428(2) . ?
C14 C15 1.404(2) . ?
C14 C16 1.433(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.363(3) . ?
C17 C18 1.413(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.362(3) . ?
C18 H18 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C1 105.08(14) . . ?
C2 C1 O1 111.99(16) . . ?
C2 C1 H1 124.0 . . ?
O1 C1 H1 124.0 . . ?
C1 C2 C7 104.82(17) . . ?
C1 C2 C3 133.45(17) . . ?
C7 C2 C3 121.27(16) . . ?
C16 O4 C22 117.75(17) . . ?
C3 C4 C5 114.17(16) . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C19 O3 C21 117.90(15) . . ?
C2 C3 C4 111.22(16) . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C6 C5 C4 111.64(15) . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C7 C6 C11 108.45(14) . . ?
C7 C6 C5 106.61(14) . . ?
C11 C6 C5 116.45(13) . . ?
C7 C6 C20 108.45(14) . . ?
C11 C6 C20 105.92(15) . . ?
C5 C6 C20 110.74(15) . . ?
C8 C7 C2 107.83(15) . . ?
C8 C7 C6 125.33(15) . . ?
C2 C7 C6 126.84(17) . . ?
C7 C8 O1 110.24(15) . . ?
C7 C8 C9 124.51(15) . . ?
O1 C8 C9 124.75(16) . . ?
O2 C9 C8 124.97(15) . . ?
O2 C9 C10 122.71(16) . . ?
C8 C9 C10 112.18(14) . . ?
C15 C10 C11 119.79(15) . . ?
C15 C10 C9 117.21(15) . . ?
C11 C10 C9 122.86(15) . . ?
C12 C11 C10 118.74(15) . . ?
C12 C11 C6 120.81(15) . . ?
C10 C11 C6 120.27(14) . . ?
C11 C12 C13 122.14(16) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C12 C13 C14 118.65(15) . . ?
C12 C13 C19 122.00(17) . . ?
C14 C13 C19 119.35(16) . . ?
C15 C14 C13 118.76(15) . . ?
C15 C14 C16 121.90(17) . . ?
C13 C14 C16 119.32(16) . . ?
C10 C15 C14 121.69(16) . . ?
C10 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
O4 C16 C17 125.90(17) . . ?
O4 C16 C14 114.65(17) . . ?
C17 C16 C14 119.45(18) . . ?
C16 C17 C18 120.96(18) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C19 C18 C17 121.32(17) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 O3 125.87(16) . . ?
C18 C19 C13 119.49(18) . . ?
O3 C19 C13 114.63(15) . . ?
C6 C20 H20A 109.5 . . ?
C6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 O1 C1 C2 -0.3(2) . . . . ?
O1 C1 C2 C7 -1.0(2) . . . . ?
O1 C1 C2 C3 171.0(2) . . . . ?
C1 C2 C3 C4 175.7(2) . . . . ?
C7 C2 C3 C4 -13.4(3) . . . . ?
C5 C4 C3 C2 38.9(3) . . . . ?
C3 C4 C5 C6 -61.2(2) . . . . ?
C4 C5 C6 C7 50.97(19) . . . . ?
C4 C5 C6 C11 172.13(16) . . . . ?
C4 C5 C6 C20 -66.81(19) . . . . ?
C1 C2 C7 C8 2.0(2) . . . . ?
C3 C2 C7 C8 -171.24(18) . . . . ?
C1 C2 C7 C6 -177.48(17) . . . . ?
C3 C2 C7 C6 9.3(3) . . . . ?
C11 C6 C7 C8 26.8(2) . . . . ?
C5 C6 C7 C8 152.91(17) . . . . ?
C20 C6 C7 C8 -87.8(2) . . . . ?
C11 C6 C7 C2 -153.87(17) . . . . ?
C5 C6 C7 C2 -27.7(2) . . . . ?
C20 C6 C7 C2 91.5(2) . . . . ?
C2 C7 C8 O1 -2.3(2) . . . . ?
C6 C7 C8 O1 177.17(15) . . . . ?
C2 C7 C8 C9 169.99(17) . . . . ?
C6 C7 C8 C9 -10.6(3) . . . . ?
C1 O1 C8 C7 1.6(2) . . . . ?
C1 O1 C8 C9 -170.61(18) . . . . ?
C7 C8 C9 O2 177.02(19) . . . . ?
O1 C8 C9 O2 -11.8(3) . . . . ?
C7 C8 C9 C10 -7.2(3) . . . . ?
O1 C8 C9 C10 163.93(17) . . . . ?
O2 C9 C10 C15 5.7(3) . . . . ?
C8 C9 C10 C15 -170.16(16) . . . . ?
O2 C9 C10 C11 -178.67(17) . . . . ?
C8 C9 C10 C11 5.5(2) . . . . ?
C15 C10 C11 C12 3.4(2) . . . . ?
C9 C10 C11 C12 -172.09(15) . . . . ?
C15 C10 C11 C6 -171.59(15) . . . . ?
C9 C10 C11 C6 12.9(2) . . . . ?
C7 C6 C11 C12 158.26(16) . . . . ?
C5 C6 C11 C12 38.1(2) . . . . ?
C20 C6 C11 C12 -85.51(19) . . . . ?
C7 C6 C11 C10 -26.8(2) . . . . ?
C5 C6 C11 C10 -147.00(15) . . . . ?
C20 C6 C11 C10 89.41(18) . . . . ?
C10 C11 C12 C13 -0.3(2) . . . . ?
C6 C11 C12 C13 174.69(16) . . . . ?
C11 C12 C13 C14 -4.0(3) . . . . ?
C11 C12 C13 C19 176.04(17) . . . . ?
C12 C13 C14 C15 5.2(2) . . . . ?
C19 C13 C14 C15 -174.85(16) . . . . ?
C12 C13 C14 C16 -176.26(16) . . . . ?
C19 C13 C14 C16 3.7(2) . . . . ?
C11 C10 C15 C14 -2.2(3) . . . . ?
C9 C10 C15 C14 173.59(16) . . . . ?
C13 C14 C15 C10 -2.2(3) . . . . ?
C16 C14 C15 C10 179.32(17) . . . . ?
C22 O4 C16 C17 9.3(3) . . . . ?
C22 O4 C16 C14 -171.21(19) . . . . ?
C15 C14 C16 O4 -4.0(3) . . . . ?
C13 C14 C16 O4 177.51(15) . . . . ?
C15 C14 C16 C17 175.55(18) . . . . ?
C13 C14 C16 C17 -2.9(3) . . . . ?
O4 C16 C17 C18 179.68(19) . . . . ?
C14 C16 C17 C18 0.2(3) . . . . ?
C16 C17 C18 C19 1.9(3) . . . . ?
C17 C18 C19 O3 179.88(17) . . . . ?
C17 C18 C19 C13 -1.1(3) . . . . ?
C21 O3 C19 C18 0.2(3) . . . . ?
C21 O3 C19 C13 -178.88(17) . . . . ?
C12 C13 C19 C18 178.26(18) . . . . ?
C14 C13 C19 C18 -1.7(3) . . . . ?
C12 C13 C19 O3 -2.6(2) . . . . ?
C14 C13 C19 O3 177.45(15) . . . . ?

_refine_diff_density_max         0.136
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.027



####################################################################### 
# 
# 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_1613
_database_code_depnum_ccdc_archive 'CCDC 2050868'
loop_
_audit_author_name
_audit_author_address
'xiaoli zhao'
;East China Normal University
China
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-02-19 downloaded from the CCDC.
;
_audit_creation_date             2020-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H30 O5, C H2 Cl2'
_chemical_formula_sum            'C26 H32 Cl2 O5'
_chemical_formula_weight         495.41
_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'
Cl Cl 0.3639 0.7018 '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                   7.44070(10)
_cell_length_b                   11.69890(10)
_cell_length_c                   28.3425(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2467.16(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    33762
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      74.0820
_cell_measurement_theta_min      3.1160
_shelx_estimated_absorpt_T_max   0.546
_shelx_estimated_absorpt_T_min   0.484
_exptl_absorpt_coefficient_mu    2.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.02838
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            55982
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.023
_diffrn_reflns_theta_max         67.023
_diffrn_reflns_theta_min         3.118
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      5.00  31.00   1.00    1.00    --    0.00  38.00 -90.00   26
  2  ω    -35.00  30.00   1.00    1.00    --    0.00 -77.00  60.00   65
  3  ω    -32.00  29.00   1.00    1.00    --    0.00 -77.00-180.00   61
  4  ω     19.00  54.00   1.00    1.00    --    0.00  57.00 -90.00   35
  5  ω    -32.00   0.00   1.00    1.00    --    0.00 -57.00  90.00   32
  6  ω    -22.00   3.00   1.00    1.00    --    0.00  57.00  90.00   25
  7  ω    -83.00 -45.00   1.00    1.00    --    0.00 -77.00  60.00   38
  8  ω    -84.00 -58.00   1.00    1.00    --    0.00 -57.00  90.00   26
  9  ω     53.00  86.00   1.00    1.00    --    0.00  38.00 -90.00   33
 10  ω     41.00  86.00   1.00    1.00    --    0.00  57.00  90.00   45
 11  ω    -19.00  89.00   1.00    1.00    --    0.00  38.00-150.00  108
 12  ω    -89.00  21.00   1.00    1.00    --    0.00 -57.00 -30.00  110
 13  ω     64.00  90.00   1.00    1.00    --   95.80  79.00  12.99   26
 14  ω    139.00 170.00   1.00    1.00    --   95.80  62.00 163.89   31
 15  ω     96.00 184.00   1.00    1.00    --   95.80  80.00  46.04   88
 16  ω     70.00 103.00   1.00    1.00    --   95.80  62.00 163.89   33
 17  ω    130.00 184.00   1.00    1.00    --   95.80  72.00 -10.37   54
 18  ω     64.00  91.00   1.00    1.00    --   95.80  80.00  46.04   27
 19  ω    133.00 181.00   1.00    1.00    --   95.80  60.00-161.68   48
 20  ω     64.00  90.00   1.00    1.00    --   95.80  82.00-120.00   26
 21  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 -90.00   26
 22  ω     67.00  97.00   1.00    1.00    --   95.80  72.00 -10.37   30
 23  ω     94.00 185.00   1.00    1.00    --   95.80  82.00-120.00   91
 24  ω      6.00 128.00   1.00    1.00    --   95.80 -82.00 -60.00  122
 25  ω     23.00 126.00   1.00    1.00    --   95.80 -82.00  90.00  103
 26  ω     75.00 184.00   1.00    1.00    --   95.80  45.00 -30.00  109
 27  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 150.00   25
 28  ω    106.00 185.00   1.00    1.00    --   95.80  82.00 150.00   79
 29  ω     65.00  90.00   1.00    1.00    --   95.80  77.00  90.00   25
 30  ω     75.00 110.00   1.00    1.00    --   95.80  45.00 -60.00   35
 31  ω     44.00 127.00   1.00    1.00    --   95.80 -82.00 150.00   83
 32  ω    146.00 185.00   1.00    1.00    --   95.80  82.00 -60.00   39
 33  ω    120.00 165.00   1.00    1.00    --   95.80  81.00 111.17   45
 34  ω    154.00 185.00   1.00    1.00    --   95.80  59.00-131.73   31
 35  ω     65.00  91.00   1.00    1.00    --   95.80  77.00   0.00   26
 36  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 -30.00   25
 37  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 -60.00   25
 38  ω     73.00  98.00   1.00    1.00    --   95.80  61.00 150.00   25
 39  ω     63.00  89.00   1.00    1.00    --   95.80  82.00  60.00   26
 40  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 41  ω     65.00  90.00   1.00    1.00    --   95.80  77.00-150.00   25
 42  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 43  ω     94.00 120.00   1.00    1.00    --   95.80 -82.00-120.00   26
 44  ω     91.00 116.00   1.00    1.00    --   95.80 -82.00   0.00   25
 45  ω     63.00  88.00   1.00    1.00    --   95.80  82.00  30.00   25
 46  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-120.00   26
 47  ω     75.00 111.00   1.00    1.00    --   95.80  45.00 120.00   36
 48  ω     71.00  97.00   1.00    1.00    --   95.80  61.00 -60.00   26
 49  ω    112.00 184.00   1.00    1.00    --   95.80  82.00  97.21   72
 50  ω     63.00  90.00   1.00    1.00    --   95.80  81.00 111.17   27
 51  ω     63.00  88.00   1.00    1.00    --   95.80  82.00-150.00   25
 52  ω     63.00  89.00   1.00    1.00    --   95.80  82.00  90.00   26
 53  ω     71.00 171.00   1.00    1.00    --   95.80  61.00  30.00  100
 54  ω     65.00 114.00   1.00    1.00    --   95.80  77.00  30.00   49
 55  ω     65.00 104.00   1.00    1.00    --   95.80  77.00  60.00   39
 56  ω     75.00 132.00   1.00    1.00    --   95.80  45.00   0.00   57
 57  ω     75.00 174.00   1.00    1.00    --   95.80  45.00 150.00   99
 58  ω     74.00 119.00   1.00    1.00    --   95.80  61.00-180.00   45
 59  ω    126.00 184.00   1.00    1.00    --   95.80  82.00-180.00   58
 60  ω     63.00  88.00   1.00    1.00    --   95.80  82.00-180.00   25
 61  ω     63.00  95.00   1.00    1.00    --   95.80  82.00  97.21   32
 62  ω    114.00 176.00   1.00    1.00    --   95.80  45.00 -60.00   62
 63  ω    136.00 183.00   1.00    1.00    --   95.80  79.00  12.99   47
 64  ω     64.00  89.00   1.00    1.00    --   95.80  79.00-134.30   25
 65  ω     71.00  96.00   1.00    1.00    --   95.80  59.00-131.73   25
 66  ω     71.00 121.00   1.00    1.00    --   95.80  60.00-161.68   50
 67  ω     76.00 153.00   1.00    1.00    --   95.80  34.00-113.70   77
;
_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      0.0829855000
_diffrn_orient_matrix_UB_12      0.0945146000
_diffrn_orient_matrix_UB_13      -0.0309098000
_diffrn_orient_matrix_UB_21      0.0057114000
_diffrn_orient_matrix_UB_22      0.0804517000
_diffrn_orient_matrix_UB_23      0.0429813000
_diffrn_orient_matrix_UB_31      0.1897400000
_diffrn_orient_matrix_UB_32      -0.0438718000
_diffrn_orient_matrix_UB_33      0.0122404000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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         0.737
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4337
_reflns_number_total             4385
_reflns_odcompleteness_completeness 99.96
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1789 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4385
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0286
_refine_ls_restrained_S_all      1.074
_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)+(0.0381P)²+0.6034P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0748
_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:
 C13(H13), C14(H14), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B), C20(H20A,
 H20B), C21(H21A,H21B), C22(H22A,H22B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C18(H18)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_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
C1 C 0.8546(3) 0.69262(17) 0.58637(7) 0.0237(4) Uani 1 1 d . . . . .
C2 C 0.9848(3) 0.78293(17) 0.58586(7) 0.0265(4) Uani 1 1 d . . . . .
C3 C 1.1197(3) 0.78318(19) 0.55357(8) 0.0323(5) Uani 1 1 d . . . . .
H3 H 1.204736 0.841462 0.553926 0.039 Uiso 1 1 calc R . . . .
C4 C 1.1318(3) 0.69504(19) 0.51933(7) 0.0315(5) Uani 1 1 d . . . . .
H4 H 1.223624 0.697032 0.497075 0.038 Uiso 1 1 calc R . . . .
C5 C 1.0111(3) 0.60757(17) 0.51853(7) 0.0259(4) Uani 1 1 d . . . . .
C6 C 0.8701(3) 0.60253(17) 0.55276(7) 0.0232(4) Uani 1 1 d . . . . .
C7 C 0.7472(3) 0.51110(17) 0.55447(7) 0.0240(4) Uani 1 1 d . . . . .
H7 H 0.759741 0.451635 0.532944 0.029 Uiso 1 1 calc R . . . .
C8 C 0.6087(3) 0.50628(16) 0.58688(7) 0.0221(4) Uani 1 1 d . . . . .
C9 C 0.4913(3) 0.39932(16) 0.59033(7) 0.0232(4) Uani 1 1 d . . . . .
C10 C 0.3731(3) 0.3910(2) 0.54577(7) 0.0305(5) Uani 1 1 d . . . . .
H10A H 0.310342 0.462909 0.541428 0.037 Uiso 1 1 calc R . . . .
H10B H 0.449978 0.379377 0.518556 0.037 Uiso 1 1 calc R . . . .
C11 C 0.2347(3) 0.2940(2) 0.54793(8) 0.0366(5) Uani 1 1 d . . . . .
H11A H 0.158030 0.297629 0.520294 0.044 Uiso 1 1 calc R . . . .
H11B H 0.296836 0.221090 0.547470 0.044 Uiso 1 1 calc R . . . .
C12 C 0.1195(3) 0.3014(2) 0.59208(8) 0.0332(5) Uani 1 1 d . . . . .
H12A H 0.040270 0.235688 0.593478 0.040 Uiso 1 1 calc R . . . .
H12B H 0.045465 0.369597 0.590555 0.040 Uiso 1 1 calc R . . . .
C13 C 0.2348(3) 0.30535(18) 0.63664(8) 0.0260(4) Uani 1 1 d . . . . .
H13 H 0.304217 0.234191 0.637470 0.031 Uiso 1 1 calc R . . . .
C14 C 0.3717(3) 0.40438(17) 0.63539(7) 0.0231(4) Uani 1 1 d . . . . .
H14 H 0.451624 0.394367 0.662553 0.028 Uiso 1 1 calc R . . . .
C15 C 0.2822(3) 0.52209(18) 0.64072(8) 0.0291(5) Uani 1 1 d . . . . .
H15A H 0.213432 0.539758 0.612578 0.035 Uiso 1 1 calc R . . . .
H15B H 0.200580 0.521220 0.667404 0.035 Uiso 1 1 calc R . . . .
C16 C 0.4244(3) 0.61152(18) 0.64817(7) 0.0284(5) Uani 1 1 d . . . . .
C17 C 0.5855(3) 0.60207(17) 0.61737(7) 0.0240(4) Uani 1 1 d . . . . .
C18 C 0.7080(3) 0.69073(17) 0.61734(7) 0.0248(4) Uani 1 1 d . . . . .
H18 H 0.692798 0.750779 0.638471 0.030 Uiso 1 1 calc R . . . .
C19 C 0.1201(3) 0.30753(18) 0.68101(8) 0.0286(5) Uani 1 1 d . . . . .
H19 H 0.028202 0.367127 0.678237 0.034 Uiso 1 1 calc R . . . .
C20 C -0.0786(4) 0.1959(2) 0.72624(10) 0.0423(6) Uani 1 1 d . . . . .
H20A H -0.129577 0.119941 0.729370 0.051 Uiso 1 1 calc R . . . .
H20B H -0.176671 0.249563 0.722093 0.051 Uiso 1 1 calc R . . . .
C21 C 0.0245(4) 0.2256(2) 0.77054(9) 0.0456(7) Uani 1 1 d . . . . .
H21A H 0.107730 0.164505 0.778136 0.055 Uiso 1 1 calc R . . . .
H21B H -0.058175 0.234389 0.796752 0.055 Uiso 1 1 calc R . . . .
C22 C 0.1272(4) 0.3362(2) 0.76292(8) 0.0423(6) Uani 1 1 d . . . . .
H22A H 0.043430 0.399523 0.761033 0.051 Uiso 1 1 calc R . . . .
H22B H 0.206790 0.349632 0.789457 0.051 Uiso 1 1 calc R . . . .
C23 C 1.0907(4) 0.9521(2) 0.62334(10) 0.0543(8) Uani 1 1 d . . . . .
H23A H 1.098420 0.993019 0.594041 0.082 Uiso 1 1 calc GR . . . .
H23B H 1.204883 0.917966 0.630352 0.082 Uiso 1 1 calc GR . . . .
H23C H 1.058421 1.004099 0.648154 0.082 Uiso 1 1 calc GR . . . .
C24 C 1.1355(4) 0.5277(2) 0.44856(8) 0.0398(6) Uani 1 1 d . . . . .
H24A H 1.124680 0.461716 0.428634 0.060 Uiso 1 1 calc GR . . . .
H24B H 1.255420 0.531774 0.460962 0.060 Uiso 1 1 calc GR . . . .
H24C H 1.110624 0.595340 0.430532 0.060 Uiso 1 1 calc GR . . . .
C25 C 0.6151(3) 0.29481(17) 0.59404(8) 0.0291(5) Uani 1 1 d . . . . .
H25A H 0.684868 0.288017 0.565687 0.044 Uiso 1 1 calc GR . . . .
H25B H 0.543762 0.227173 0.598189 0.044 Uiso 1 1 calc GR . . . .
H25C H 0.694080 0.303849 0.620558 0.044 Uiso 1 1 calc GR . . . .
O1 O 0.2306(2) 0.33010(14) 0.72017(5) 0.0344(4) Uani 1 1 d . . . . .
O2 O 0.0368(2) 0.19942(13) 0.68552(6) 0.0355(4) Uani 1 1 d . . . . .
O3 O 1.0104(2) 0.51921(12) 0.48657(5) 0.0322(4) Uani 1 1 d . . . . .
O4 O 0.9574(2) 0.86505(12) 0.61959(5) 0.0331(4) Uani 1 1 d . . . . .
O5 O 0.4079(2) 0.68788(14) 0.67702(6) 0.0429(4) Uani 1 1 d . . . . .
C26 C 0.5396(5) 0.5722(3) 0.77446(11) 0.0590(8) Uani 1 1 d . . . . .
H26A H 0.443605 0.595978 0.753481 0.071 Uiso 1 1 calc R . . . .
H26B H 0.618252 0.637284 0.779275 0.071 Uiso 1 1 calc R . . . .
Cl1 Cl 0.66079(12) 0.46293(8) 0.74772(3) 0.0693(3) Uani 1 1 d . . . . .
Cl2 Cl 0.44702(11) 0.53195(6) 0.82864(2) 0.05350(19) 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 1.433(3) . ?
C1 C6 1.425(3) . ?
C1 C18 1.400(3) . ?
C2 C3 1.359(3) . ?
C2 O4 1.371(2) . ?
C3 C4 1.419(3) . ?
C4 C5 1.362(3) . ?
C5 C6 1.430(3) . ?
C5 O3 1.374(2) . ?
C6 C7 1.408(3) . ?
C7 C8 1.382(3) . ?
C8 C9 1.529(3) . ?
C8 C17 1.426(3) . ?
C9 C10 1.542(3) . ?
C9 C14 1.558(3) . ?
C9 C25 1.534(3) . ?
C10 C11 1.534(3) . ?
C11 C12 1.519(3) . ?
C12 C13 1.528(3) . ?
C13 C14 1.543(3) . ?
C13 C19 1.520(3) . ?
C14 C15 1.537(3) . ?
C15 C16 1.503(3) . ?
C16 C17 1.487(3) . ?
C16 O5 1.217(3) . ?
C17 C18 1.381(3) . ?
C19 O1 1.406(3) . ?
C19 O2 1.414(3) . ?
C20 C21 1.512(4) . ?
C20 O2 1.439(3) . ?
C21 C22 1.518(4) . ?
C22 O1 1.437(3) . ?
C23 O4 1.426(3) . ?
C24 O3 1.427(3) . ?
C26 Cl1 1.738(3) . ?
C26 Cl2 1.748(3) . ?

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 118.91(19) . . ?
C18 C1 C2 122.98(18) . . ?
C18 C1 C6 118.07(19) . . ?
C3 C2 C1 120.53(19) . . ?
C3 C2 O4 125.30(19) . . ?
O4 C2 C1 114.16(19) . . ?
C2 C3 C4 120.4(2) . . ?
C5 C4 C3 121.0(2) . . ?
C4 C5 C6 120.25(19) . . ?
C4 C5 O3 125.33(19) . . ?
O3 C5 C6 114.43(18) . . ?
C1 C6 C5 118.84(19) . . ?
C7 C6 C1 119.08(18) . . ?
C7 C6 C5 122.08(18) . . ?
C8 C7 C6 122.57(18) . . ?
C7 C8 C9 120.13(17) . . ?
C7 C8 C17 117.47(18) . . ?
C17 C8 C9 122.36(18) . . ?
C8 C9 C10 108.97(16) . . ?
C8 C9 C14 110.35(15) . . ?
C8 C9 C25 108.27(17) . . ?
C10 C9 C14 110.36(17) . . ?
C25 C9 C10 110.37(17) . . ?
C25 C9 C14 108.49(16) . . ?
C11 C10 C9 113.39(18) . . ?
C12 C11 C10 111.66(19) . . ?
C11 C12 C13 111.46(18) . . ?
C12 C13 C14 111.96(17) . . ?
C19 C13 C12 111.68(18) . . ?
C19 C13 C14 112.15(17) . . ?
C13 C14 C9 111.57(16) . . ?
C15 C14 C9 111.24(16) . . ?
C15 C14 C13 112.61(17) . . ?
C16 C15 C14 109.44(18) . . ?
C17 C16 C15 115.67(17) . . ?
O5 C16 C15 122.3(2) . . ?
O5 C16 C17 122.0(2) . . ?
C8 C17 C16 120.79(19) . . ?
C18 C17 C8 120.67(19) . . ?
C18 C17 C16 118.47(18) . . ?
C17 C18 C1 121.76(18) . . ?
O1 C19 C13 109.17(17) . . ?
O1 C19 O2 110.66(18) . . ?
O2 C19 C13 107.81(17) . . ?
O2 C20 C21 110.9(2) . . ?
C20 C21 C22 109.5(2) . . ?
O1 C22 C21 110.3(2) . . ?
C19 O1 C22 111.24(18) . . ?
C19 O2 C20 111.09(16) . . ?
C5 O3 C24 116.28(17) . . ?
C2 O4 C23 116.74(19) . . ?
Cl1 C26 Cl2 112.92(18) . . ?

_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 26.983
_oxdiff_exptl_absorpt_empirical_full_min 0.476
