# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2020

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

data_mo_dd18180_0m
_database_code_depnum_ccdc_archive 'CCDC 1869826'
loop_
_audit_author_name
_audit_author_address
'Huang fei'
;Nanjing Tech University
China
;
_audit_update_record             
;
2018-09-26 deposited with the CCDC.	2020-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H25 Cl O4'
_chemical_formula_weight         448.92

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'
Cl Cl 0.1484 0.1585 '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                   8.4738(2)
_cell_length_b                   24.4748(6)
_cell_length_c                   11.8708(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.0510(10)
_cell_angle_gamma                90
_cell_volume                     2461.52(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8292
_cell_measurement_theta_min      4.782
_cell_measurement_theta_max      52.952

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.184
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6652
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            29317
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.391
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             4295
_reflns_number_gt                3078
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

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

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1227P)²+0.8060P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.030(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4295
_refine_ls_number_parameters     346
_refine_ls_number_restraints     138
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.2209
_refine_ls_wR_factor_gt          0.1953
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.007
_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
Cl1 Cl 0.31325(17) 0.49635(4) 0.91333(12) 0.1321(6) Uani 1 1 d . . . . .
O1 O 0.5312(2) 0.66485(10) 0.41647(19) 0.0851(7) Uani 1 1 d . . . . .
H1 H 0.5199 0.6901 0.4611 0.128 Uiso 1 1 calc R U . . .
O2 O 0.6363(2) 0.70268(7) 0.64514(15) 0.0632(5) Uani 1 1 d . . . . .
O3 O 0.3498(2) 0.73307(9) 0.56072(17) 0.0803(6) Uani 1 1 d . . . . .
O4 O 0.2738(3) 0.75951(9) 0.73102(18) 0.0802(6) Uani 1 1 d . . . . .
C1 C 0.6844(4) 0.64810(12) 0.4192(2) 0.0695(8) Uani 1 1 d . . . . .
C2 C 0.7135(5) 0.59639(14) 0.3772(3) 0.0892(10) Uani 1 1 d . . . . .
H2 H 0.6302 0.5742 0.3536 0.107 Uiso 1 1 calc R U . . .
C3 C 0.8687(5) 0.57762(15) 0.3706(3) 0.0985(11) Uani 1 1 d . . . . .
H3 H 0.8874 0.5430 0.3417 0.118 Uiso 1 1 calc R U . . .
C4 C 0.9940(4) 0.60908(16) 0.4057(3) 0.0913(10) Uani 1 1 d D . . . .
C5 C 0.9623(4) 0.66034(14) 0.4459(3) 0.0790(8) Uani 1 1 d . . . . .
H5 H 1.0466 0.6823 0.4684 0.095 Uiso 1 1 calc R U . . .
C6 C 0.8095(3) 0.68117(12) 0.4546(2) 0.0655(7) Uani 1 1 d . . . . .
C7 C 0.7874(3) 0.73753(11) 0.4980(2) 0.0626(7) Uani 1 1 d . . . . .
C8 C 0.8587(4) 0.78216(13) 0.4465(3) 0.0766(8) Uani 1 1 d . . . . .
H8 H 0.9136 0.7762 0.3805 0.092 Uiso 1 1 calc R U . . .
C9 C 0.8522(4) 0.83454(12) 0.4882(3) 0.0799(9) Uani 1 1 d D . . . .
C10 C 0.7672(4) 0.84281(12) 0.5848(3) 0.0770(8) Uani 1 1 d . . . . .
H10 H 0.7608 0.8778 0.6150 0.092 Uiso 1 1 calc R U . . .
C11 C 0.6917(3) 0.80038(11) 0.6375(2) 0.0660(7) Uani 1 1 d . . . . .
H11 H 0.6336 0.8070 0.7018 0.079 Uiso 1 1 calc R U . . .
C12 C 0.7021(3) 0.74827(11) 0.5952(2) 0.0603(7) Uani 1 1 d . . . . .
C13 C 1.161(2) 0.5851(10) 0.4099(19) 0.158(2) Uani 0.5 1 d D U P A 1
H13A H 1.2351 0.6135 0.4316 0.189 Uiso 0.5 1 calc R U P A 1
H13B H 1.1661 0.5567 0.4669 0.189 Uiso 0.5 1 calc R U P A 1
C14 C 1.2057(14) 0.5625(5) 0.3032(12) 0.160(2) Uani 0.5 1 d D U P A 1
H14 H 1.1136 0.5468 0.2742 0.191 Uiso 0.5 1 calc R U P A 1
C15 C 1.2958(16) 0.5544(6) 0.2380(13) 0.178(3) Uani 0.5 1 d D U P A 1
H15A H 1.3989 0.5665 0.2489 0.214 Uiso 0.5 1 calc R U P A 1
H15B H 1.2678 0.5354 0.1727 0.214 Uiso 0.5 1 calc R U P A 1
C13' C 1.167(2) 0.5917(9) 0.392(2) 0.158(2) Uani 0.5 1 d D U P A 2
H13C H 1.1929 0.5967 0.3132 0.190 Uiso 0.5 1 calc R U P A 2
H13D H 1.2323 0.6167 0.4353 0.190 Uiso 0.5 1 calc R U P A 2
C14' C 1.2069(14) 0.5412(6) 0.4208(12) 0.164(2) Uani 0.5 1 d D U P A 2
H14' H 1.2001 0.5289 0.4947 0.197 Uiso 0.5 1 calc R U P A 2
C15' C 1.2586(15) 0.5086(6) 0.3367(14) 0.179(3) Uani 0.5 1 d D U P A 2
H15C H 1.2641 0.5221 0.2636 0.215 Uiso 0.5 1 calc R U P A 2
H15D H 1.2885 0.4728 0.3520 0.215 Uiso 0.5 1 calc R U P A 2
C16 C 0.9525(12) 0.8797(4) 0.4350(9) 0.1055(17) Uani 0.6 1 d D U P B 1
H16A H 0.9557 0.9114 0.4841 0.127 Uiso 0.6 1 calc R U P B 1
H16B H 1.0597 0.8668 0.4258 0.127 Uiso 0.6 1 calc R U P B 1
C17 C 0.8838(10) 0.8949(3) 0.3248(6) 0.1066(16) Uani 0.6 1 d D U P B 1
H17 H 0.7779 0.9049 0.3261 0.128 Uiso 0.6 1 calc R U P B 1
C18 C 0.9431(15) 0.8966(4) 0.2319(9) 0.118(2) Uani 0.5 1 d D U P B 1
H18A H 1.0486 0.8873 0.2235 0.141 Uiso 0.5 1 calc R U P B 1
H18B H 0.8827 0.9073 0.1694 0.141 Uiso 0.5 1 calc R U P B 1
C16' C 0.906(2) 0.8848(7) 0.4239(14) 0.1070(18) Uani 0.4 1 d D U P B 2
H16C H 0.8142 0.9074 0.4073 0.128 Uiso 0.4 1 calc R U P B 2
H16D H 0.9766 0.9058 0.4722 0.128 Uiso 0.4 1 calc R U P B 2
C17' C 0.9818(17) 0.8735(5) 0.3235(9) 0.1106(17) Uani 0.4 1 d D U P B 2
H17' H 1.0554 0.8478 0.3483 0.133 Uiso 0.4 1 calc R U P B 2
C18' C 1.0121(14) 0.8757(4) 0.2282(9) 0.118(2) Uani 0.5 1 d D U P B 2
H18C H 0.9555 0.8989 0.1804 0.141 Uiso 0.5 1 calc R U P B 2
H18D H 1.0928 0.8542 0.1999 0.141 Uiso 0.5 1 calc R U P B 2
C19 C 0.5128(3) 0.71152(11) 0.7228(2) 0.0610(7) Uani 1 1 d . . . . .
H19 H 0.5489 0.7361 0.7831 0.073 Uiso 1 1 calc R U . . .
C20 C 0.4684(3) 0.65674(11) 0.7714(2) 0.0601(7) Uani 1 1 d . . . . .
C21 C 0.4443(4) 0.65120(12) 0.8846(2) 0.0694(7) Uani 1 1 d . . . . .
H21 H 0.4594 0.6810 0.9322 0.083 Uiso 1 1 calc R U . . .
C22 C 0.3980(4) 0.60174(13) 0.9286(3) 0.0800(9) Uani 1 1 d . . . . .
H22 H 0.3817 0.5981 1.0055 0.096 Uiso 1 1 calc R U . . .
C23 C 0.3762(4) 0.55835(13) 0.8589(3) 0.0830(9) Uani 1 1 d . . . . .
C24 C 0.4021(5) 0.56251(14) 0.7457(3) 0.0940(11) Uani 1 1 d . . . . .
H24 H 0.3884 0.5324 0.6988 0.113 Uiso 1 1 calc R U . . .
C25 C 0.4482(5) 0.61148(13) 0.7027(3) 0.0845(9) Uani 1 1 d . . . . .
H25 H 0.4664 0.6145 0.6259 0.101 Uiso 1 1 calc R U . . .
C26 C 0.3716(3) 0.73611(11) 0.6608(2) 0.0623(7) Uani 1 1 d . . . . .
C27 C 0.1307(4) 0.78167(19) 0.6810(4) 0.1064(13) Uani 1 1 d . . . . .
H27A H 0.1569 0.8052 0.6195 0.160 Uiso 1 1 calc R U . . .
H27B H 0.0750 0.8022 0.7366 0.160 Uiso 1 1 calc R U . . .
H27C H 0.0651 0.7523 0.6538 0.160 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
Cl1 C23 1.737(3) . ?
O1 C1 1.361(4) . ?
O1 H1 0.8200 . ?
O2 C12 1.385(3) . ?
O2 C19 1.424(3) . ?
O3 C26 1.201(3) . ?
O4 C26 1.317(3) . ?
O4 C27 1.446(4) . ?
C1 C2 1.384(4) . ?
C1 C6 1.393(4) . ?
C2 C3 1.396(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(5) . ?
C4 C13 1.530(15) . ?
C4 C13' 1.535(15) . ?
C5 C6 1.397(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.486(4) . ?
C7 C8 1.395(4) . ?
C7 C12 1.398(4) . ?
C8 C9 1.375(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.381(5) . ?
C9 C16' 1.521(14) . ?
C9 C16 1.537(10) . ?
C10 C11 1.375(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(4) . ?
C11 H11 0.9300 . ?
C13 C14 1.440(18) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.115(12) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9300 . ?
C15 H15B 0.9300 . ?
C13' C14' 1.326(18) . ?
C13' H13C 0.9700 . ?
C13' H13D 0.9700 . ?
C14' C15' 1.358(13) . ?
C14' H14' 0.9300 . ?
C15' H15C 0.9300 . ?
C15' H15D 0.9300 . ?
C16 C17 1.470(11) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.222(10) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9300 . ?
C18 H18B 0.9300 . ?
C16' C17' 1.394(16) . ?
C16' H16C 0.9700 . ?
C16' H16D 0.9700 . ?
C17' C18' 1.166(12) . ?
C17' H17' 0.9300 . ?
C18' H18C 0.9300 . ?
C18' H18D 0.9300 . ?
C19 C20 1.510(4) . ?
C19 C26 1.518(4) . ?
C19 H19 0.9800 . ?
C20 C21 1.370(4) . ?
C20 C25 1.384(4) . ?
C21 C22 1.378(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.357(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.369(5) . ?
C24 C25 1.363(5) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C12 O2 C19 117.43(19) . . ?
C26 O4 C27 115.9(3) . . ?
O1 C1 C2 116.3(3) . . ?
O1 C1 C6 123.6(3) . . ?
C2 C1 C6 120.0(3) . . ?
C1 C2 C3 119.7(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 121.6(3) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C5 C4 C3 117.6(3) . . ?
C5 C4 C13 121.8(11) . . ?
C3 C4 C13 120.3(11) . . ?
C5 C4 C13' 119.0(10) . . ?
C3 C4 C13' 123.1(10) . . ?
C4 C5 C6 123.2(3) . . ?
C4 C5 H5 118.4 . . ?
C6 C5 H5 118.4 . . ?
C1 C6 C5 117.9(3) . . ?
C1 C6 C7 123.0(3) . . ?
C5 C6 C7 119.2(3) . . ?
C8 C7 C12 116.7(3) . . ?
C8 C7 C6 121.1(2) . . ?
C12 C7 C6 122.1(2) . . ?
C9 C8 C7 123.5(3) . . ?
C9 C8 H8 118.2 . . ?
C7 C8 H8 118.2 . . ?
C8 C9 C10 117.4(3) . . ?
C8 C9 C16' 124.0(7) . . ?
C10 C9 C16' 117.6(7) . . ?
C8 C9 C16 119.8(5) . . ?
C10 C9 C16 122.4(5) . . ?
C11 C10 C9 121.4(3) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 O2 124.3(2) . . ?
C11 C12 C7 120.9(2) . . ?
O2 C12 C7 114.8(2) . . ?
C14 C13 C4 112.2(14) . . ?
C14 C13 H13A 109.2 . . ?
C4 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C4 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 151.0(16) . . ?
C15 C14 H14 104.5 . . ?
C13 C14 H14 104.5 . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C14' C13' C4 118.1(16) . . ?
C14' C13' H13C 107.8 . . ?
C4 C13' H13C 107.8 . . ?
C14' C13' H13D 107.8 . . ?
C4 C13' H13D 107.8 . . ?
H13C C13' H13D 107.1 . . ?
C13' C14' C15' 116.1(17) . . ?
C13' C14' H14' 121.9 . . ?
C15' C14' H14' 121.9 . . ?
C14' C15' H15C 120.0 . . ?
C14' C15' H15D 120.0 . . ?
H15C C15' H15D 120.0 . . ?
C17 C16 C9 109.5(7) . . ?
C17 C16 H16A 109.8 . . ?
C9 C16 H16A 109.8 . . ?
C17 C16 H16B 109.8 . . ?
C9 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
C18 C17 C16 130.5(10) . . ?
C18 C17 H17 114.7 . . ?
C16 C17 H17 114.7 . . ?
C17 C18 H18A 120.0 . . ?
C17 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?
C17' C16' C9 114.5(12) . . ?
C17' C16' H16C 108.6 . . ?
C9 C16' H16C 108.6 . . ?
C17' C16' H16D 108.6 . . ?
C9 C16' H16D 108.6 . . ?
H16C C16' H16D 107.6 . . ?
C18' C17' C16' 159.1(16) . . ?
C18' C17' H17' 100.4 . . ?
C16' C17' H17' 100.4 . . ?
C17' C18' H18C 120.0 . . ?
C17' C18' H18D 120.0 . . ?
H18C C18' H18D 120.0 . . ?
O2 C19 C20 107.7(2) . . ?
O2 C19 C26 109.2(2) . . ?
C20 C19 C26 109.7(2) . . ?
O2 C19 H19 110.1 . . ?
C20 C19 H19 110.1 . . ?
C26 C19 H19 110.1 . . ?
C21 C20 C25 118.7(3) . . ?
C21 C20 C19 120.3(2) . . ?
C25 C20 C19 121.0(2) . . ?
C20 C21 C22 120.4(3) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 119.5(3) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 121.2(3) . . ?
C22 C23 Cl1 119.7(3) . . ?
C24 C23 Cl1 119.1(3) . . ?
C25 C24 C23 119.0(3) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C24 C25 C20 121.1(3) . . ?
C24 C25 H25 119.5 . . ?
C20 C25 H25 119.5 . . ?
O3 C26 O4 124.4(3) . . ?
O3 C26 C19 124.1(2) . . ?
O4 C26 C19 111.4(2) . . ?
O4 C27 H27A 109.5 . . ?
O4 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O4 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 176.0(3) . . . . ?
C6 C1 C2 C3 0.0(5) . . . . ?
C1 C2 C3 C4 0.6(6) . . . . ?
C2 C3 C4 C5 -1.2(6) . . . . ?
C2 C3 C4 C13 173.1(10) . . . . ?
C2 C3 C4 C13' -175.2(11) . . . . ?
C3 C4 C5 C6 1.3(6) . . . . ?
C13 C4 C5 C6 -172.9(11) . . . . ?
C13' C4 C5 C6 175.6(11) . . . . ?
O1 C1 C6 C5 -175.6(3) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
O1 C1 C6 C7 2.9(4) . . . . ?
C2 C1 C6 C7 178.5(3) . . . . ?
C4 C5 C6 C1 -0.8(5) . . . . ?
C4 C5 C6 C7 -179.3(3) . . . . ?
C1 C6 C7 C8 -121.5(3) . . . . ?
C5 C6 C7 C8 56.9(4) . . . . ?
C1 C6 C7 C12 62.0(4) . . . . ?
C5 C6 C7 C12 -119.5(3) . . . . ?
C12 C7 C8 C9 1.8(5) . . . . ?
C6 C7 C8 C9 -174.8(3) . . . . ?
C7 C8 C9 C10 -1.4(5) . . . . ?
C7 C8 C9 C16' -169.6(9) . . . . ?
C7 C8 C9 C16 171.8(5) . . . . ?
C8 C9 C10 C11 -0.1(5) . . . . ?
C16' C9 C10 C11 168.9(8) . . . . ?
C16 C9 C10 C11 -173.1(5) . . . . ?
C9 C10 C11 C12 1.1(5) . . . . ?
C10 C11 C12 O2 177.0(3) . . . . ?
C10 C11 C12 C7 -0.7(4) . . . . ?
C19 O2 C12 C11 20.0(4) . . . . ?
C19 O2 C12 C7 -162.2(2) . . . . ?
C8 C7 C12 C11 -0.7(4) . . . . ?
C6 C7 C12 C11 175.9(3) . . . . ?
C8 C7 C12 O2 -178.5(2) . . . . ?
C6 C7 C12 O2 -1.9(4) . . . . ?
C5 C4 C13 C14 -130.9(15) . . . . ?
C3 C4 C13 C14 55(2) . . . . ?
C13' C4 C13 C14 -54(10) . . . . ?
C4 C13 C14 C15 143(3) . . . . ?
C5 C4 C13' C14' 139.3(17) . . . . ?
C3 C4 C13' C14' -47(2) . . . . ?
C13 C4 C13' C14' 31(9) . . . . ?
C4 C13' C14' C15' 116.7(18) . . . . ?
C8 C9 C16 C17 73.5(9) . . . . ?
C10 C9 C16 C17 -113.6(8) . . . . ?
C16' C9 C16 C17 -36(3) . . . . ?
C9 C16 C17 C18 -125.7(10) . . . . ?
C8 C9 C16' C17' -7.8(18) . . . . ?
C10 C9 C16' C17' -176.0(11) . . . . ?
C16 C9 C16' C17' 72(3) . . . . ?
C9 C16' C17' C18' 130(3) . . . . ?
C12 O2 C19 C20 -176.3(2) . . . . ?
C12 O2 C19 C26 64.7(3) . . . . ?
O2 C19 C20 C21 136.0(3) . . . . ?
C26 C19 C20 C21 -105.3(3) . . . . ?
O2 C19 C20 C25 -45.2(4) . . . . ?
C26 C19 C20 C25 73.4(3) . . . . ?
C25 C20 C21 C22 -1.3(5) . . . . ?
C19 C20 C21 C22 177.5(3) . . . . ?
C20 C21 C22 C23 0.1(5) . . . . ?
C21 C22 C23 C24 1.1(5) . . . . ?
C21 C22 C23 Cl1 -178.5(3) . . . . ?
C22 C23 C24 C25 -1.0(6) . . . . ?
Cl1 C23 C24 C25 178.6(3) . . . . ?
C23 C24 C25 C20 -0.3(6) . . . . ?
C21 C20 C25 C24 1.4(5) . . . . ?
C19 C20 C25 C24 -177.4(3) . . . . ?
C27 O4 C26 O3 1.1(5) . . . . ?
C27 O4 C26 C19 -176.7(3) . . . . ?
O2 C19 C26 O3 20.5(4) . . . . ?
C20 C19 C26 O3 -97.2(3) . . . . ?
O2 C19 C26 O4 -161.6(2) . . . . ?
C20 C19 C26 O4 80.6(3) . . . . ?

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.042

_shelxl_version_number           2013-4

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

data_mo_dd19077_0m
_database_code_depnum_ccdc_archive 'CCDC 1917686'
loop_
_audit_author_name
_audit_author_address
'Huang fei'
;Nanjing Tech University
China
;
_audit_update_record             
;
2019-05-22 deposited with the CCDC.	2020-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 O4'
_chemical_formula_weight         362.40

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'
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                   15.0906(5)
_cell_length_b                   7.9886(2)
_cell_length_c                   15.7975(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.5440(10)
_cell_angle_gamma                90
_cell_volume                     1895.52(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9888
_cell_measurement_theta_min      5.181
_cell_measurement_theta_max      54.647

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6709
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            27913
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.888
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3693
_reflns_number_gt                3028
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

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

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0571P)²+0.4436P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.030(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3693
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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 0.44596(10) 0.24565(16) 0.55558(7) 0.0795(4) Uani 1 1 d . . . . .
H1 H 0.4504 0.3211 0.5910 0.119 Uiso 1 1 calc R U . . .
O2 O 0.38295(10) 0.55773(15) 0.54923(7) 0.0769(4) Uani 1 1 d . . . . .
O3 O 0.36707(7) -0.15993(13) 0.29018(9) 0.0691(4) Uani 1 1 d . . . . .
O4 O 0.43054(6) 0.06450(12) 0.23848(7) 0.0510(3) Uani 1 1 d . . . . .
C1 C 0.36993(10) 0.18529(17) 0.42111(9) 0.0485(4) Uani 1 1 d . . . . .
H1A H 0.3952 0.0790 0.4238 0.058 Uiso 1 1 calc R U . . .
C2 C 0.39077(11) 0.29556(19) 0.48648(9) 0.0535(4) Uani 1 1 d . . . . .
C3 C 0.35548(11) 0.45710(19) 0.48135(9) 0.0542(4) Uani 1 1 d . . . . .
C4 C 0.29774(11) 0.50134(18) 0.41252(10) 0.0531(4) Uani 1 1 d . . . . .
H4 H 0.2742 0.6090 0.4096 0.064 Uiso 1 1 calc R U . . .
C5 C 0.27352(9) 0.38831(18) 0.34671(9) 0.0458(3) Uani 1 1 d . . . . .
C6 C 0.31149(9) 0.22929(16) 0.35057(8) 0.0414(3) Uani 1 1 d . . . . .
C7 C 0.28663(8) 0.10196(16) 0.28030(8) 0.0405(3) Uani 1 1 d . . . . .
H7 H 0.2755 0.1643 0.2269 0.049 Uiso 1 1 calc R U . . .
C8 C 0.20233(9) 0.00392(17) 0.29287(9) 0.0442(3) Uani 1 1 d . . . . .
C9 C 0.14693(9) -0.05888(17) 0.22160(10) 0.0479(4) Uani 1 1 d . . . . .
C10 C 0.16394(11) -0.0305(2) 0.13618(10) 0.0593(4) Uani 1 1 d . . . . .
H10 H 0.2147 0.0283 0.1249 0.071 Uiso 1 1 calc R U . . .
C11 C 0.10693(13) -0.0880(3) 0.07006(13) 0.0798(6) Uani 1 1 d . . . . .
H11 H 0.1182 -0.0650 0.0144 0.096 Uiso 1 1 calc R U . . .
C12 C 0.03171(13) -0.1813(3) 0.08555(15) 0.0903(7) Uani 1 1 d . . . . .
H12 H -0.0066 -0.2203 0.0402 0.108 Uiso 1 1 calc R U . . .
C13 C 0.01445(11) -0.2147(2) 0.16606(15) 0.0795(6) Uani 1 1 d . . . . .
H13 H -0.0351 -0.2790 0.1754 0.095 Uiso 1 1 calc R U . . .
C14 C 0.06999(10) -0.15414(19) 0.23642(12) 0.0583(4) Uani 1 1 d . . . . .
C15 C 0.05081(11) -0.1845(2) 0.32044(13) 0.0687(5) Uani 1 1 d . . . . .
H15 H 0.0015 -0.2488 0.3304 0.082 Uiso 1 1 calc R U . . .
C16 C 0.10332(12) -0.1212(2) 0.38671(13) 0.0706(5) Uani 1 1 d . . . . .
H16 H 0.0892 -0.1401 0.4419 0.085 Uiso 1 1 calc R U . . .
C17 C 0.17904(10) -0.0270(2) 0.37286(10) 0.0575(4) Uani 1 1 d . . . . .
H17 H 0.2144 0.0155 0.4194 0.069 Uiso 1 1 calc R U . . .
C18 C 0.36392(9) -0.01576(16) 0.27057(8) 0.0423(3) Uani 1 1 d . . . . .
C19 C 0.51223(10) -0.0293(2) 0.23408(12) 0.0635(4) Uani 1 1 d . . . . .
H19A H 0.5010 -0.1231 0.1966 0.095 Uiso 1 1 calc R U . . .
H19B H 0.5333 -0.0686 0.2898 0.095 Uiso 1 1 calc R U . . .
H19C H 0.5564 0.0418 0.2129 0.095 Uiso 1 1 calc R U . . .
C20 C 0.20599(11) 0.4425(2) 0.27453(10) 0.0590(4) Uani 1 1 d . . . . .
H20A H 0.1639 0.3520 0.2621 0.071 Uiso 1 1 calc R U . . .
H20B H 0.1731 0.5375 0.2935 0.071 Uiso 1 1 calc R U . . .
C21 C 0.24401(12) 0.4890(2) 0.19562(11) 0.0660(5) Uani 1 1 d . . . . .
H21 H 0.2915 0.5636 0.2003 0.079 Uiso 1 1 calc R U . . .
C22 C 0.2173(2) 0.4353(3) 0.12025(15) 0.0988(8) Uani 1 1 d . . . . .
C23 C 0.36131(16) 0.7300(2) 0.54287(14) 0.0844(6) Uani 1 1 d . . . . .
H23A H 0.3811 0.7747 0.4915 0.127 Uiso 1 1 calc R U . . .
H23B H 0.3902 0.7885 0.5909 0.127 Uiso 1 1 calc R U . . .
H23C H 0.2980 0.7435 0.5419 0.127 Uiso 1 1 calc R U . . .
H22A H 0.1730(16) 0.350(3) 0.1086(15) 0.107(8) Uiso 1 1 d . . . . .
H22B H 0.2436(19) 0.474(4) 0.071(2) 0.138(10) Uiso 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
O1 C2 1.3670(18) . ?
O1 H1 0.8200 . ?
O2 C3 1.3718(18) . ?
O2 C23 1.415(2) . ?
O3 C18 1.1924(17) . ?
O4 C18 1.3332(16) . ?
O4 C19 1.4498(17) . ?
C1 C2 1.371(2) . ?
C1 C6 1.3975(18) . ?
C1 H1A 0.9300 . ?
C2 C3 1.395(2) . ?
C3 C4 1.372(2) . ?
C4 C5 1.399(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3925(18) . ?
C5 C20 1.517(2) . ?
C6 C7 1.5256(18) . ?
C7 C8 1.5232(18) . ?
C7 C18 1.5175(18) . ?
C7 H7 0.9800 . ?
C8 C17 1.367(2) . ?
C8 C9 1.427(2) . ?
C9 C10 1.416(2) . ?
C9 C14 1.426(2) . ?
C10 C11 1.367(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.399(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.349(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.411(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.407(3) . ?
C15 C16 1.349(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.403(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.469(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.293(3) . ?
C21 H21 0.9300 . ?
C22 H22A 0.96(3) . ?
C22 H22B 0.96(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C2 O1 H1 109.5 . . ?
C3 O2 C23 117.64(14) . . ?
C18 O4 C19 116.46(11) . . ?
C2 C1 C6 121.36(13) . . ?
C2 C1 H1A 119.3 . . ?
C6 C1 H1A 119.3 . . ?
O1 C2 C1 119.47(14) . . ?
O1 C2 C3 121.05(14) . . ?
C1 C2 C3 119.48(14) . . ?
O2 C3 C4 126.10(14) . . ?
O2 C3 C2 114.31(14) . . ?
C4 C3 C2 119.58(14) . . ?
C3 C4 C5 121.53(13) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 118.66(13) . . ?
C6 C5 C20 122.48(13) . . ?
C4 C5 C20 118.85(13) . . ?
C5 C6 C1 119.31(13) . . ?
C5 C6 C7 120.35(12) . . ?
C1 C6 C7 120.29(12) . . ?
C8 C7 C18 110.75(11) . . ?
C8 C7 C6 113.43(11) . . ?
C18 C7 C6 110.46(10) . . ?
C8 C7 H7 107.3 . . ?
C18 C7 H7 107.3 . . ?
C6 C7 H7 107.3 . . ?
C17 C8 C9 118.85(13) . . ?
C17 C8 C7 120.42(13) . . ?
C9 C8 C7 120.73(12) . . ?
C10 C9 C14 117.87(14) . . ?
C10 C9 C8 123.31(13) . . ?
C14 C9 C8 118.83(14) . . ?
C11 C10 C9 121.03(16) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 120.28(18) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 121.35(17) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 121.56(16) . . ?
C15 C14 C9 119.47(15) . . ?
C13 C14 C9 118.98(17) . . ?
C16 C15 C14 120.57(15) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.42(17) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C8 C17 C16 121.83(16) . . ?
C8 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
O3 C18 O4 123.42(13) . . ?
O3 C18 C7 125.73(13) . . ?
O4 C18 C7 110.83(11) . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C5 114.88(13) . . ?
C21 C20 H20A 108.5 . . ?
C5 C20 H20A 108.5 . . ?
C21 C20 H20B 108.5 . . ?
C5 C20 H20B 108.5 . . ?
H20A C20 H20B 107.5 . . ?
C22 C21 C20 125.8(2) . . ?
C22 C21 H21 117.1 . . ?
C20 C21 H21 117.1 . . ?
C21 C22 H22A 124.1(15) . . ?
C21 C22 H22B 121.8(18) . . ?
H22A C22 H22B 114(2) . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C6 C1 C2 O1 177.88(14) . . . . ?
C6 C1 C2 C3 -2.3(2) . . . . ?
C23 O2 C3 C4 -10.3(3) . . . . ?
C23 O2 C3 C2 170.48(17) . . . . ?
O1 C2 C3 O2 1.7(2) . . . . ?
C1 C2 C3 O2 -178.21(14) . . . . ?
O1 C2 C3 C4 -177.66(15) . . . . ?
C1 C2 C3 C4 2.5(2) . . . . ?
O2 C3 C4 C5 -179.56(15) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C3 C4 C5 C6 -2.0(2) . . . . ?
C3 C4 C5 C20 177.10(15) . . . . ?
C4 C5 C6 C1 2.2(2) . . . . ?
C20 C5 C6 C1 -176.86(13) . . . . ?
C4 C5 C6 C7 179.76(12) . . . . ?
C20 C5 C6 C7 0.7(2) . . . . ?
C2 C1 C6 C5 -0.1(2) . . . . ?
C2 C1 C6 C7 -177.65(13) . . . . ?
C5 C6 C7 C8 -84.83(15) . . . . ?
C1 C6 C7 C8 92.66(15) . . . . ?
C5 C6 C7 C18 150.15(12) . . . . ?
C1 C6 C7 C18 -32.36(16) . . . . ?
C18 C7 C8 C17 95.05(15) . . . . ?
C6 C7 C8 C17 -29.81(18) . . . . ?
C18 C7 C8 C9 -84.19(15) . . . . ?
C6 C7 C8 C9 150.95(12) . . . . ?
C17 C8 C9 C10 178.47(14) . . . . ?
C7 C8 C9 C10 -2.3(2) . . . . ?
C17 C8 C9 C14 -1.0(2) . . . . ?
C7 C8 C9 C14 178.22(12) . . . . ?
C14 C9 C10 C11 2.0(2) . . . . ?
C8 C9 C10 C11 -177.48(16) . . . . ?
C9 C10 C11 C12 -2.1(3) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C11 C12 C13 C14 1.5(3) . . . . ?
C12 C13 C14 C15 178.10(18) . . . . ?
C12 C13 C14 C9 -1.4(3) . . . . ?
C10 C9 C14 C15 -179.83(14) . . . . ?
C8 C9 C14 C15 -0.3(2) . . . . ?
C10 C9 C14 C13 -0.3(2) . . . . ?
C8 C9 C14 C13 179.24(14) . . . . ?
C13 C14 C15 C16 -178.00(17) . . . . ?
C9 C14 C15 C16 1.5(2) . . . . ?
C14 C15 C16 C17 -1.4(3) . . . . ?
C9 C8 C17 C16 1.2(2) . . . . ?
C7 C8 C17 C16 -178.04(14) . . . . ?
C15 C16 C17 C8 0.0(3) . . . . ?
C19 O4 C18 O3 -4.7(2) . . . . ?
C19 O4 C18 C7 173.85(12) . . . . ?
C8 C7 C18 O3 -17.3(2) . . . . ?
C6 C7 C18 O3 109.18(16) . . . . ?
C8 C7 C18 O4 164.19(11) . . . . ?
C6 C7 C18 O4 -69.29(14) . . . . ?
C6 C5 C20 C21 -78.6(2) . . . . ?
C4 C5 C20 C21 102.30(17) . . . . ?
C5 C20 C21 C22 130.6(2) . . . . ?

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.027

_shelxl_version_number           2013-4

