# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2099175'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2021-07-26 deposited with the CCDC.	2021-09-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H24 O5'
_chemical_formula_sum            'C29 H24 O5'
_chemical_formula_weight         452.48

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/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                   13.937(5)
_cell_length_b                   11.056(3)
_cell_length_c                   15.432(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.595(10)
_cell_angle_gamma                90
_cell_volume                     2370.3(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4914
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      22.73

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6878
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_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            21664
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.354
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4644
_reflns_number_gt                2505
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0565P)²+0.4804P] 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         4644
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1317
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1371
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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 0.2839(2) 0.4267(3) -0.15852(19) 0.0768(9) Uani 1 1 d . . . . .
C2 C 0.2673(3) 0.3727(4) -0.2392(2) 0.1047(13) Uani 1 1 d . . . . .
H2 H 0.3077 0.3896 -0.2828 0.126 Uiso 1 1 calc R U . . .
C3 C 0.1926(3) 0.2953(3) -0.2551(2) 0.1033(12) Uani 1 1 d . . . . .
H3 H 0.1833 0.2581 -0.3092 0.124 Uiso 1 1 calc R U . . .
C4 C 0.1303(2) 0.2706(3) -0.19249(18) 0.0822(9) Uani 1 1 d . . . . .
H4 H 0.0783 0.2188 -0.2045 0.099 Uiso 1 1 calc R U . . .
C5 C 0.1461(2) 0.3236(2) -0.11203(16) 0.0623(7) Uani 1 1 d . . . . .
H5 H 0.1044 0.3067 -0.0695 0.075 Uiso 1 1 calc R U . . .
C6 C 0.22296(18) 0.4019(2) -0.09288(15) 0.0535(6) Uani 1 1 d . . . . .
C7 C 0.24066(18) 0.4593(2) -0.00804(15) 0.0544(6) Uani 1 1 d . . . . .
C8 C 0.17937(15) 0.4326(2) 0.06473(14) 0.0458(6) Uani 1 1 d . . . . .
C9 C 0.12618(15) 0.52452(19) 0.10170(14) 0.0445(6) Uani 1 1 d . . . . .
C10 C 0.12100(15) 0.64848(19) 0.06398(14) 0.0453(6) Uani 1 1 d . . . . .
C11 C 0.14599(17) 0.7483(2) 0.11523(16) 0.0548(6) Uani 1 1 d . . . . .
H11 H 0.1627 0.7383 0.1744 0.066 Uiso 1 1 calc R U . . .
C12 C 0.14625(18) 0.8629(2) 0.07891(18) 0.0620(7) Uani 1 1 d . . . . .
H12 H 0.1642 0.9286 0.1142 0.074 Uiso 1 1 calc R U . . .
C13 C 0.12044(17) 0.8822(2) -0.00860(17) 0.0560(7) Uani 1 1 d . . . . .
C14 C 0.1215(2) 1.0083(2) -0.04606(19) 0.0836(9) Uani 1 1 d . . . . .
H14A H 0.0945 1.0068 -0.1053 0.125 Uiso 1 1 calc R U . . .
H14B H 0.1865 1.0372 -0.0441 0.125 Uiso 1 1 calc R U . . .
H14C H 0.0840 1.0610 -0.0127 0.125 Uiso 1 1 calc R U . . .
C15 C 0.09250(17) 0.7830(2) -0.05855(16) 0.0585(7) Uani 1 1 d . . . . .
H15 H 0.0726 0.7938 -0.1170 0.070 Uiso 1 1 calc R U . . .
C16 C 0.09341(17) 0.6676(2) -0.02351(15) 0.0549(6) Uani 1 1 d . . . . .
H16 H 0.0753 0.6021 -0.0590 0.066 Uiso 1 1 calc R U . . .
C17 C 0.18362(15) 0.3195(2) 0.10279(14) 0.0478(6) Uani 1 1 d . . . . .
H17 H 0.2189 0.2590 0.0780 0.057 Uiso 1 1 calc R U . . .
C18 C 0.13692(15) 0.29292(19) 0.17700(13) 0.0428(5) Uani 1 1 d . . . . .
C19 C 0.14922(17) 0.1677(2) 0.21146(13) 0.0468(6) Uani 1 1 d . . . . .
C20 C 0.0781(2) 0.0077(2) 0.28551(18) 0.0740(8) Uani 1 1 d . . . . .
H20A H 0.0976 -0.0536 0.2465 0.111 Uiso 1 1 calc R U . . .
H20B H 0.0171 -0.0138 0.3060 0.111 Uiso 1 1 calc R U . . .
H20C H 0.1253 0.0146 0.3340 0.111 Uiso 1 1 calc R U . . .
C21 C 0.08000(15) 0.49688(19) 0.17557(13) 0.0454(6) Uani 1 1 d . . . . .
H21 H 0.0448 0.5575 0.2002 0.055 Uiso 1 1 calc R U . . .
C22 C 0.08344(15) 0.38371(19) 0.21468(13) 0.0430(5) Uani 1 1 d . . . . .
C23 C 0.03316(15) 0.36640(19) 0.29551(14) 0.0438(5) Uani 1 1 d . . . . .
C24 C 0.08122(18) 0.3280(2) 0.37194(16) 0.0648(7) Uani 1 1 d . . . . .
H24 H 0.1464 0.3096 0.3726 0.078 Uiso 1 1 calc R U . . .
C25 C 0.03537(19) 0.3160(3) 0.44787(15) 0.0691(8) Uani 1 1 d . . . . .
H25 H 0.0696 0.2901 0.4987 0.083 Uiso 1 1 calc R U . . .
C26 C -0.06083(17) 0.3425(2) 0.44751(15) 0.0558(6) Uani 1 1 d . . . . .
C27 C -0.0636(2) 0.3110(3) 0.60023(17) 0.0947(10) Uani 1 1 d . . . . .
H27A H -0.0360 0.2314 0.6008 0.142 Uiso 1 1 calc R U . . .
H27B H -0.1073 0.3169 0.6451 0.142 Uiso 1 1 calc R U . . .
H27C H -0.0134 0.3699 0.6103 0.142 Uiso 1 1 calc R U . . .
C28 C -0.11009(18) 0.3810(2) 0.37170(16) 0.0623(7) Uani 1 1 d . . . . .
H28 H -0.1754 0.3986 0.3709 0.075 Uiso 1 1 calc R U . . .
C29 C -0.06311(17) 0.3936(2) 0.29715(15) 0.0557(6) Uani 1 1 d . . . . .
H29 H -0.0972 0.4211 0.2467 0.067 Uiso 1 1 calc R U . . .
O1 O 0.35888(18) 0.5040(2) -0.14504(15) 0.1107(8) Uani 1 1 d . . . . .
H1 H 0.3634 0.5260 -0.0941 0.166 Uiso 1 1 calc R U . . .
O2 O 0.30774(14) 0.53196(18) 0.00679(12) 0.0825(6) Uani 1 1 d . . . . .
O3 O 0.22282(13) 0.11137(14) 0.21109(11) 0.0651(5) Uani 1 1 d . . . . .
O4 O 0.06931(11) 0.12237(14) 0.24028(11) 0.0612(5) Uani 1 1 d . . . . .
O5 O -0.11402(13) 0.33257(18) 0.51840(11) 0.0798(6) 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 O1 1.353(4) . ?
C1 C2 1.383(5) . ?
C1 C6 1.400(3) . ?
C2 C3 1.355(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.458(3) . ?
C7 O2 1.240(3) . ?
C7 C8 1.494(3) . ?
C8 C17 1.380(3) . ?
C8 C9 1.406(3) . ?
C9 C21 1.387(3) . ?
C9 C10 1.489(3) . ?
C10 C11 1.386(3) . ?
C10 C16 1.390(3) . ?
C11 C12 1.386(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(3) . ?
C12 H12 0.9300 . ?
C13 C15 1.379(3) . ?
C13 C14 1.509(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.386(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.393(3) . ?
C17 H17 0.9300 . ?
C18 C22 1.404(3) . ?
C18 C19 1.488(3) . ?
C19 O3 1.201(3) . ?
C19 O4 1.330(3) . ?
C20 O4 1.447(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.388(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.491(3) . ?
C23 C24 1.376(3) . ?
C23 C29 1.377(3) . ?
C24 C25 1.385(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.372(3) . ?
C25 H25 0.9300 . ?
C26 O5 1.374(3) . ?
C26 C28 1.376(3) . ?
C27 O5 1.415(3) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C29 1.376(3) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
O1 H1 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 118.8(3) . . ?
O1 C1 C6 121.2(3) . . ?
C2 C1 C6 119.9(3) . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 118.1(3) . . ?
C5 C6 C7 122.2(2) . . ?
C1 C6 C7 119.7(3) . . ?
O2 C7 C6 121.2(2) . . ?
O2 C7 C8 117.2(2) . . ?
C6 C7 C8 121.6(2) . . ?
C17 C8 C9 119.24(19) . . ?
C17 C8 C7 119.4(2) . . ?
C9 C8 C7 120.9(2) . . ?
C21 C9 C8 117.9(2) . . ?
C21 C9 C10 120.86(19) . . ?
C8 C9 C10 121.19(18) . . ?
C11 C10 C16 118.1(2) . . ?
C11 C10 C9 120.5(2) . . ?
C16 C10 C9 121.4(2) . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 121.8(2) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C15 C13 C12 117.5(2) . . ?
C15 C13 C14 122.1(2) . . ?
C12 C13 C14 120.4(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 C16 121.4(2) . . ?
C13 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C10 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
C10 C16 H16 119.6 . . ?
C8 C17 C18 122.3(2) . . ?
C8 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C17 C18 C22 119.2(2) . . ?
C17 C18 C19 116.23(19) . . ?
C22 C18 C19 124.54(18) . . ?
O3 C19 O4 123.0(2) . . ?
O3 C19 C18 123.7(2) . . ?
O4 C19 C18 113.2(2) . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C9 C21 C22 123.6(2) . . ?
C9 C21 H21 118.2 . . ?
C22 C21 H21 118.2 . . ?
C21 C22 C18 117.73(18) . . ?
C21 C22 C23 118.50(18) . . ?
C18 C22 C23 123.74(19) . . ?
C24 C23 C29 117.4(2) . . ?
C24 C23 C22 121.8(2) . . ?
C29 C23 C22 120.7(2) . . ?
C23 C24 C25 121.9(2) . . ?
C23 C24 H24 119.0 . . ?
C25 C24 H24 119.0 . . ?
C26 C25 C24 119.5(2) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 O5 124.7(2) . . ?
C25 C26 C28 119.4(2) . . ?
O5 C26 C28 115.9(2) . . ?
O5 C27 H27A 109.5 . . ?
O5 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O5 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C26 120.3(2) . . ?
C29 C28 H28 119.9 . . ?
C26 C28 H28 119.9 . . ?
C28 C29 C23 121.5(2) . . ?
C28 C29 H29 119.2 . . ?
C23 C29 H29 119.2 . . ?
C1 O1 H1 109.5 . . ?
C19 O4 C20 116.80(19) . . ?
C26 O5 C27 117.6(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.82 1.80 2.522(3) 146.8 .

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_3h
_database_code_depnum_ccdc_archive 'CCDC 2099176'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2021-07-26 deposited with the CCDC.	2021-09-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H21 Cl O5'
_chemical_formula_sum            'C28 H21 Cl O5'
_chemical_formula_weight         472.90

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6420(9)
_cell_length_b                   9.6811(10)
_cell_length_c                   14.0972(13)
_cell_angle_alpha                83.296(3)
_cell_angle_beta                 76.282(3)
_cell_angle_gamma                66.624(3)
_cell_volume                     1173.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6691
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      26.86

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.200
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6578
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_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            16665
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.293
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4586
_reflns_number_gt                3181
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0386P)²+0.3089P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.055(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4586
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1034
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_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 0.9071(2) -0.0389(2) 0.67691(15) 0.0643(5) Uani 1 1 d . . . . .
C2 C 0.8558(3) -0.0400(3) 0.59300(18) 0.0825(7) Uani 1 1 d . . . . .
H2 H 0.8838 -0.1306 0.5630 0.099 Uiso 1 1 calc R U . . .
C3 C 0.7649(3) 0.0902(3) 0.55444(18) 0.0870(7) Uani 1 1 d . . . . .
H3 H 0.7313 0.0877 0.4983 0.104 Uiso 1 1 calc R U . . .
C4 C 0.7213(3) 0.2273(3) 0.59773(17) 0.0817(7) Uani 1 1 d . . . . .
H4 H 0.6578 0.3159 0.5714 0.098 Uiso 1 1 calc R U . . .
C5 C 0.7733(2) 0.2301(2) 0.67986(15) 0.0644(5) Uani 1 1 d . . . . .
H5 H 0.7447 0.3217 0.7088 0.077 Uiso 1 1 calc R U . . .
C6 C 0.8682(2) 0.0983(2) 0.72086(13) 0.0513(5) Uani 1 1 d . . . . .
C7 C 0.92350(19) 0.0992(2) 0.80918(13) 0.0487(4) Uani 1 1 d . . . . .
C8 C 0.88594(18) 0.24492(18) 0.85583(12) 0.0434(4) Uani 1 1 d . . . . .
C9 C 0.93820(18) 0.35800(18) 0.81086(12) 0.0428(4) Uani 1 1 d . . . . .
C10 C 1.05134(19) 0.33797(19) 0.71595(12) 0.0446(4) Uani 1 1 d . . . . .
C11 C 1.0360(2) 0.4556(2) 0.64716(13) 0.0567(5) Uani 1 1 d . . . . .
H11 H 0.9503 0.5455 0.6590 0.068 Uiso 1 1 calc R U . . .
C12 C 1.1458(3) 0.4416(3) 0.56152(14) 0.0658(6) Uani 1 1 d . . . . .
H12 H 1.1346 0.5214 0.5164 0.079 Uiso 1 1 calc R U . . .
C13 C 1.2712(2) 0.3086(3) 0.54405(13) 0.0638(6) Uani 1 1 d . . . . .
C14 C 1.2905(2) 0.1899(2) 0.61028(14) 0.0624(5) Uani 1 1 d . . . . .
H14 H 1.3762 0.1003 0.5976 0.075 Uiso 1 1 calc R U . . .
C15 C 1.1808(2) 0.2054(2) 0.69594(13) 0.0522(5) Uani 1 1 d . . . . .
H15 H 1.1939 0.1255 0.7411 0.063 Uiso 1 1 calc R U . . .
C16 C 0.79575(18) 0.26483(19) 0.95016(12) 0.0451(4) Uani 1 1 d . . . . .
H16 H 0.7645 0.1884 0.9808 0.054 Uiso 1 1 calc R U . . .
C17 C 0.75194(17) 0.39618(18) 0.99908(12) 0.0423(4) Uani 1 1 d . . . . .
C18 C 0.6648(2) 0.40532(19) 1.10285(13) 0.0486(4) Uani 1 1 d . . . . .
C19 C 0.6695(3) 0.4455(3) 1.26365(15) 0.0937(8) Uani 1 1 d . . . . .
H19A H 0.5859 0.5423 1.2679 0.140 Uiso 1 1 calc R U . . .
H19B H 0.7407 0.4443 1.3015 0.140 Uiso 1 1 calc R U . . .
H19C H 0.6295 0.3691 1.2885 0.140 Uiso 1 1 calc R U . . .
C20 C 0.88837(18) 0.49098(19) 0.86020(12) 0.0440(4) Uani 1 1 d . . . . .
H20 H 0.9198 0.5674 0.8298 0.053 Uiso 1 1 calc R U . . .
C21 C 0.79365(17) 0.51497(18) 0.95295(12) 0.0418(4) Uani 1 1 d . . . . .
C22 C 0.73887(17) 0.66067(18) 1.00111(11) 0.0413(4) Uani 1 1 d . . . . .
C23 C 0.58714(19) 0.72628(19) 1.05192(13) 0.0494(4) Uani 1 1 d . . . . .
H23 H 0.5194 0.6790 1.0535 0.059 Uiso 1 1 calc R U . . .
C24 C 0.53408(19) 0.8594(2) 1.10012(13) 0.0501(4) Uani 1 1 d . . . . .
H24 H 0.4321 0.9008 1.1340 0.060 Uiso 1 1 calc R U . . .
C25 C 0.63372(19) 0.93086(18) 1.09776(12) 0.0450(4) Uani 1 1 d . . . . .
C26 C 0.4417(2) 1.1251(2) 1.20070(15) 0.0687(6) Uani 1 1 d . . . . .
H26A H 0.3692 1.1458 1.1595 0.103 Uiso 1 1 calc R U . . .
H26B H 0.4277 1.2170 1.2282 0.103 Uiso 1 1 calc R U . . .
H26C H 0.4251 1.0557 1.2523 0.103 Uiso 1 1 calc R U . . .
C27 C 0.78449(19) 0.87004(19) 1.04458(12) 0.0462(4) Uani 1 1 d . . . . .
H27 H 0.8509 0.9194 1.0412 0.055 Uiso 1 1 calc R U . . .
C28 C 0.83586(18) 0.73719(18) 0.99698(12) 0.0431(4) Uani 1 1 d . . . . .
H28 H 0.9370 0.6977 0.9615 0.052 Uiso 1 1 calc R U . . .
Cl1 Cl 1.4114(5) 0.2897(4) 0.43649(19) 0.0990(7) Uani 0.912(15) 1 d . . P A 1
Cl1' Cl 1.362(4) 0.323(3) 0.4194(14) 0.0990(7) Uani 0.088(15) 1 d . . P A 2
O1 O 0.9937(2) -0.17207(17) 0.71289(13) 0.0911(5) Uani 1 1 d . . . . .
H1 H 1.0167 -0.1585 0.7625 0.137 Uiso 1 1 calc R U . . .
O2 O 0.99502(16) -0.01965(14) 0.84952(10) 0.0647(4) Uani 1 1 d . . . . .
O3 O 0.53824(15) 0.40280(16) 1.12968(10) 0.0679(4) Uani 1 1 d . . . . .
O4 O 0.74840(14) 0.41679(15) 1.16286(9) 0.0610(4) Uani 1 1 d . . . . .
O5 O 0.59528(15) 1.06064(14) 1.14435(10) 0.0616(4) 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 O1 1.345(3) . ?
C1 C2 1.389(3) . ?
C1 C6 1.405(3) . ?
C2 C3 1.357(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.468(3) . ?
C7 O2 1.236(2) . ?
C7 C8 1.500(2) . ?
C8 C16 1.393(2) . ?
C8 C9 1.407(2) . ?
C9 C20 1.390(2) . ?
C9 C10 1.489(2) . ?
C10 C15 1.390(2) . ?
C10 C11 1.392(2) . ?
C11 C12 1.384(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(3) . ?
C13 Cl1 1.748(2) . ?
C13 Cl1' 1.784(15) . ?
C14 C15 1.382(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.383(2) . ?
C16 H16 0.9300 . ?
C17 C21 1.406(2) . ?
C17 C18 1.497(2) . ?
C18 O3 1.198(2) . ?
C18 O4 1.339(2) . ?
C19 O4 1.445(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.391(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.480(2) . ?
C22 C23 1.389(2) . ?
C22 C28 1.393(2) . ?
C23 C24 1.379(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.382(2) . ?
C24 H24 0.9300 . ?
C25 O5 1.362(2) . ?
C25 C27 1.389(2) . ?
C26 O5 1.427(2) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.374(2) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
O1 H1 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 117.6(2) . . ?
O1 C1 C6 122.53(19) . . ?
C2 C1 C6 119.9(2) . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 121.0(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.3(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 118.19(18) . . ?
C5 C6 C7 122.01(17) . . ?
C1 C6 C7 119.77(18) . . ?
O2 C7 C6 120.95(17) . . ?
O2 C7 C8 118.46(16) . . ?
C6 C7 C8 120.49(16) . . ?
C16 C8 C9 119.48(15) . . ?
C16 C8 C7 116.45(14) . . ?
C9 C8 C7 124.06(14) . . ?
C20 C9 C8 118.21(14) . . ?
C20 C9 C10 118.72(15) . . ?
C8 C9 C10 122.97(15) . . ?
C15 C10 C11 117.84(16) . . ?
C15 C10 C9 121.26(15) . . ?
C11 C10 C9 120.76(16) . . ?
C12 C11 C10 121.28(18) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C11 119.15(19) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 121.26(17) . . ?
C12 C13 Cl1 119.6(2) . . ?
C14 C13 Cl1 119.1(2) . . ?
C12 C13 Cl1' 105.0(11) . . ?
C14 C13 Cl1' 132.7(10) . . ?
C13 C14 C15 119.16(19) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C10 121.31(17) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
C17 C16 C8 121.14(15) . . ?
C17 C16 H16 119.4 . . ?
C8 C16 H16 119.4 . . ?
C16 C17 C21 120.32(15) . . ?
C16 C17 C18 118.19(15) . . ?
C21 C17 C18 121.45(15) . . ?
O3 C18 O4 124.03(16) . . ?
O3 C18 C17 125.53(17) . . ?
O4 C18 C17 110.44(14) . . ?
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 . . ?
C9 C20 C21 122.98(15) . . ?
C9 C20 H20 118.5 . . ?
C21 C20 H20 118.5 . . ?
C20 C21 C17 117.64(15) . . ?
C20 C21 C22 121.01(14) . . ?
C17 C21 C22 121.35(14) . . ?
C23 C22 C28 117.62(15) . . ?
C23 C22 C21 120.58(15) . . ?
C28 C22 C21 121.79(14) . . ?
C24 C23 C22 121.91(16) . . ?
C24 C23 H23 119.0 . . ?
C22 C23 H23 119.0 . . ?
C23 C24 C25 119.46(15) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
O5 C25 C24 124.61(15) . . ?
O5 C25 C27 115.77(15) . . ?
C24 C25 C27 119.61(16) . . ?
O5 C26 H26A 109.5 . . ?
O5 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O5 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 C25 120.28(16) . . ?
C28 C27 H27 119.9 . . ?
C25 C27 H27 119.9 . . ?
C27 C28 C22 121.04(15) . . ?
C27 C28 H28 119.5 . . ?
C22 C28 H28 119.5 . . ?
C1 O1 H1 109.5 . . ?
C18 O4 C19 115.73(15) . . ?
C25 O5 C26 117.19(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.82 1.84 2.565(2) 146.0 .

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.030

