# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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_shelxl
_audit_block_doi                 10.5517/ccdc.csd.cc22bcqj
_database_code_depnum_ccdc_archive 'CCDC 1916597'
loop_
_audit_author_name
_audit_author_address
LTYa
;nankai university
China
;
_audit_update_record             
;
2019-05-17 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H20 Cl N O3 S'
_chemical_formula_weight         449.93

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   13.132(3)
_cell_length_b                   8.2538(17)
_cell_length_c                   20.537(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.43(3)
_cell_angle_gamma                90
_cell_volume                     2145.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    6238
_cell_measurement_theta_min      1.6087
_cell_measurement_theta_max      27.8664

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.303
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8498
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            24767
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.609
_diffrn_reflns_theta_max         27.835
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5069
_reflns_number_gt                4157
_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       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0841P)²+0.1154P] 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         5069
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1297
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.002
_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
S1 S 0.26314(3) 0.68127(5) 0.31049(2) 0.02289(13) Uani 1 1 d . . . . .
Cl1 Cl 0.37222(3) 0.23067(7) 0.52779(2) 0.03746(15) Uani 1 1 d . . . . .
O1 O 0.18273(11) 0.77272(15) 0.26452(7) 0.0326(3) Uani 1 1 d . . . . .
O2 O 0.37140(10) 0.70357(15) 0.31149(7) 0.0313(3) Uani 1 1 d . . . . .
O3 O 0.04739(9) 0.20080(16) 0.45336(6) 0.0308(3) Uani 1 1 d . . . . .
N1 N 0.23578(10) 0.48536(16) 0.29363(7) 0.0204(3) Uani 1 1 d . . . . .
C1 C 0.25074(13) 0.72066(18) 0.39242(8) 0.0207(3) Uani 1 1 d . . . . .
C2 C 0.15456(13) 0.77055(19) 0.40134(9) 0.0231(3) Uani 1 1 d . . . . .
H2 H 0.093995 0.777564 0.363865 0.028 Uiso 1 1 calc R U . . .
C3 C 0.14797(14) 0.8102(2) 0.46584(9) 0.0253(4) Uani 1 1 d . . . . .
H3 H 0.082433 0.845912 0.472046 0.030 Uiso 1 1 calc R U . . .
C4 C 0.23528(14) 0.7986(2) 0.52150(9) 0.0272(4) Uani 1 1 d . . . . .
C5 C 0.33044(14) 0.7425(2) 0.51142(10) 0.0303(4) Uani 1 1 d . . . . .
H5 H 0.390258 0.730722 0.549129 0.036 Uiso 1 1 calc R U . . .
C6 C 0.33909(13) 0.7039(2) 0.44762(10) 0.0264(4) Uani 1 1 d . . . . .
H6 H 0.404257 0.666426 0.441396 0.032 Uiso 1 1 calc R U . . .
C7 C 0.22719(16) 0.8503(3) 0.59024(10) 0.0385(5) Uani 1 1 d . . . . .
H7A H 0.245946 0.965105 0.597199 0.058 Uiso 1 1 calc R U . . .
H7B H 0.275698 0.785346 0.624988 0.058 Uiso 1 1 calc R U . . .
H7C H 0.154673 0.834096 0.593286 0.058 Uiso 1 1 calc R U . . .
C8 C 0.31688(12) 0.3630(2) 0.31026(8) 0.0190(3) Uani 1 1 d . . . . .
C9 C 0.40672(13) 0.3748(2) 0.28616(8) 0.0228(3) Uani 1 1 d . . . . .
H9 H 0.415904 0.465808 0.259959 0.027 Uiso 1 1 calc R U . . .
C10 C 0.48238(13) 0.2532(2) 0.30066(9) 0.0252(4) Uani 1 1 d . . . . .
H10 H 0.544367 0.263331 0.285449 0.030 Uiso 1 1 calc R U . . .
C11 C 0.46873(13) 0.1174(2) 0.33698(8) 0.0253(4) Uani 1 1 d . . . . .
H11 H 0.520698 0.034403 0.346474 0.030 Uiso 1 1 calc R U . . .
C12 C 0.37802(13) 0.1039(2) 0.35942(8) 0.0226(3) Uani 1 1 d . . . . .
H12 H 0.368169 0.010464 0.384056 0.027 Uiso 1 1 calc R U . . .
C13 C 0.30138(12) 0.22507(19) 0.34639(8) 0.0194(3) Uani 1 1 d . . . . .
C14 C 0.20383(13) 0.20484(19) 0.36889(8) 0.0206(3) Uani 1 1 d . . . . .
H14 H 0.184187 0.091587 0.377907 0.025 Uiso 1 1 calc R U . . .
C15 C 0.17756(12) 0.33804(19) 0.41366(8) 0.0188(3) Uani 1 1 d . . . . .
H15 H 0.227414 0.431734 0.425106 0.023 Uiso 1 1 calc R U . . .
C16 C 0.11413(12) 0.32043(19) 0.34042(8) 0.0199(3) Uani 1 1 d . . . . .
H16 H 0.041562 0.274311 0.333259 0.024 Uiso 1 1 calc R U . . .
C17 C 0.12803(12) 0.4337(2) 0.28775(8) 0.0213(3) Uani 1 1 d . . . . .
C18 C 0.05001(14) 0.4797(2) 0.23581(9) 0.0303(4) Uani 1 1 d . . . . .
H18A H 0.064179 0.547357 0.201826 0.036 Uiso 1 1 calc R U . . .
H18B H -0.020192 0.445137 0.232497 0.036 Uiso 1 1 calc R U . . .
C19 C 0.12762(12) 0.28138(19) 0.46679(8) 0.0207(3) Uani 1 1 d . . . . .
C20 C 0.17840(13) 0.3312(2) 0.53814(8) 0.0220(3) Uani 1 1 d . . . . .
C21 C 0.11406(14) 0.3940(2) 0.57635(9) 0.0288(4) Uani 1 1 d . . . . .
H21 H 0.039961 0.400523 0.556896 0.035 Uiso 1 1 calc R U . . .
C22 C 0.15595(16) 0.4467(3) 0.64176(10) 0.0378(5) Uani 1 1 d . . . . .
H22 H 0.110934 0.490682 0.666617 0.045 Uiso 1 1 calc R U . . .
C23 C 0.26329(17) 0.4354(3) 0.67111(9) 0.0373(5) Uani 1 1 d . . . . .
H23 H 0.291921 0.471562 0.716201 0.045 Uiso 1 1 calc R U . . .
C24 C 0.32921(15) 0.3719(2) 0.63522(9) 0.0338(4) Uani 1 1 d . . . . .
H24 H 0.402990 0.363417 0.655513 0.041 Uiso 1 1 calc R U . . .
C25 C 0.28673(13) 0.3207(2) 0.56938(9) 0.0255(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
S1 O2 1.4282(13) . ?
S1 O1 1.4302(14) . ?
S1 N1 1.6726(14) . ?
S1 C1 1.7633(17) . ?
Cl1 C25 1.7471(18) . ?
O3 C19 1.2140(19) . ?
N1 C8 1.441(2) . ?
N1 C17 1.452(2) . ?
C1 C2 1.386(2) . ?
C1 C6 1.397(3) . ?
C2 C3 1.389(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.399(3) . ?
C4 C7 1.505(3) . ?
C5 C6 1.382(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.399(2) . ?
C8 C13 1.403(2) . ?
C9 C10 1.388(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.482(2) . ?
C14 C16 1.508(2) . ?
C14 C15 1.530(2) . ?
C14 H14 1.0000 . ?
C15 C19 1.490(2) . ?
C15 C16 1.520(2) . ?
C15 H15 1.0000 . ?
C16 C17 1.477(2) . ?
C16 H16 1.0000 . ?
C17 C18 1.323(2) . ?
C18 H18A 0.9500 . ?
C18 H18B 0.9500 . ?
C19 C20 1.497(2) . ?
C20 C21 1.397(2) . ?
C20 C25 1.399(2) . ?
C21 C22 1.380(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.381(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(3) . ?
C24 H24 0.9500 . ?

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
O2 S1 O1 119.92(8) . . ?
O2 S1 N1 106.60(7) . . ?
O1 S1 N1 107.06(8) . . ?
O2 S1 C1 107.86(8) . . ?
O1 S1 C1 107.05(8) . . ?
N1 S1 C1 107.85(7) . . ?
C8 N1 C17 117.15(13) . . ?
C8 N1 S1 121.59(11) . . ?
C17 N1 S1 116.89(10) . . ?
C2 C1 C6 120.77(16) . . ?
C2 C1 S1 119.97(13) . . ?
C6 C1 S1 119.25(13) . . ?
C1 C2 C3 119.08(16) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 121.39(16) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 118.35(17) . . ?
C3 C4 C7 120.20(17) . . ?
C5 C4 C7 121.43(17) . . ?
C6 C5 C4 121.24(17) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 119.12(16) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 119.88(15) . . ?
C9 C8 N1 120.46(14) . . ?
C13 C8 N1 119.47(13) . . ?
C10 C9 C8 119.79(15) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C11 C10 C9 120.89(16) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 119.23(15) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C11 C12 C13 121.14(15) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C8 119.02(14) . . ?
C12 C13 C14 119.95(14) . . ?
C8 C13 C14 121.01(14) . . ?
C13 C14 C16 117.30(14) . . ?
C13 C14 C15 117.26(13) . . ?
C16 C14 C15 60.04(10) . . ?
C13 C14 H14 116.7 . . ?
C16 C14 H14 116.7 . . ?
C15 C14 H14 116.7 . . ?
C19 C15 C16 117.55(13) . . ?
C19 C15 C14 115.34(13) . . ?
C16 C15 C14 59.24(10) . . ?
C19 C15 H15 117.3 . . ?
C16 C15 H15 117.3 . . ?
C14 C15 H15 117.3 . . ?
C17 C16 C14 116.64(13) . . ?
C17 C16 C15 121.47(13) . . ?
C14 C16 C15 60.71(10) . . ?
C17 C16 H16 115.6 . . ?
C14 C16 H16 115.6 . . ?
C15 C16 H16 115.6 . . ?
C18 C17 N1 120.75(15) . . ?
C18 C17 C16 123.51(15) . . ?
N1 C17 C16 115.64(13) . . ?
C17 C18 H18A 120.0 . . ?
C17 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?
O3 C19 C15 122.01(15) . . ?
O3 C19 C20 120.43(15) . . ?
C15 C19 C20 117.54(14) . . ?
C21 C20 C25 117.30(16) . . ?
C21 C20 C19 118.25(15) . . ?
C25 C20 C19 124.44(15) . . ?
C22 C21 C20 121.33(18) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C21 C22 C23 120.01(18) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 C24 120.30(18) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C25 119.36(18) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C24 C25 C20 121.69(16) . . ?
C24 C25 Cl1 117.58(14) . . ?
C20 C25 Cl1 120.63(13) . . ?

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
O2 S1 N1 C8 26.15(14) . . . . ?
O1 S1 N1 C8 155.64(12) . . . . ?
C1 S1 N1 C8 -89.47(13) . . . . ?
O2 S1 N1 C17 -178.03(11) . . . . ?
O1 S1 N1 C17 -48.54(13) . . . . ?
C1 S1 N1 C17 66.36(13) . . . . ?
O2 S1 C1 C2 154.64(13) . . . . ?
O1 S1 C1 C2 24.33(15) . . . . ?
N1 S1 C1 C2 -90.58(14) . . . . ?
O2 S1 C1 C6 -24.19(15) . . . . ?
O1 S1 C1 C6 -154.50(13) . . . . ?
N1 S1 C1 C6 90.60(14) . . . . ?
C6 C1 C2 C3 2.6(2) . . . . ?
S1 C1 C2 C3 -176.24(12) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C2 C3 C4 C7 176.90(17) . . . . ?
C3 C4 C5 C6 1.9(3) . . . . ?
C7 C4 C5 C6 -176.26(17) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C2 C1 C6 C5 -2.0(3) . . . . ?
S1 C1 C6 C5 176.85(13) . . . . ?
C17 N1 C8 C9 148.60(14) . . . . ?
S1 N1 C8 C9 -55.63(18) . . . . ?
C17 N1 C8 C13 -26.4(2) . . . . ?
S1 N1 C8 C13 129.42(13) . . . . ?
C13 C8 C9 C10 -2.8(2) . . . . ?
N1 C8 C9 C10 -177.76(14) . . . . ?
C8 C9 C10 C11 2.0(2) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C11 C12 C13 -0.5(2) . . . . ?
C11 C12 C13 C8 -0.3(2) . . . . ?
C11 C12 C13 C14 177.92(15) . . . . ?
C9 C8 C13 C12 2.0(2) . . . . ?
N1 C8 C13 C12 176.97(14) . . . . ?
C9 C8 C13 C14 -176.24(14) . . . . ?
N1 C8 C13 C14 -1.3(2) . . . . ?
C12 C13 C14 C16 -166.79(14) . . . . ?
C8 C13 C14 C16 11.4(2) . . . . ?
C12 C13 C14 C15 124.69(16) . . . . ?
C8 C13 C14 C15 -57.1(2) . . . . ?
C13 C14 C15 C19 -144.35(15) . . . . ?
C16 C14 C15 C19 108.28(15) . . . . ?
C13 C14 C15 C16 107.36(16) . . . . ?
C13 C14 C16 C17 5.5(2) . . . . ?
C15 C14 C16 C17 112.85(15) . . . . ?
C13 C14 C16 C15 -107.31(15) . . . . ?
C19 C15 C16 C17 150.41(14) . . . . ?
C14 C15 C16 C17 -105.04(16) . . . . ?
C19 C15 C16 C14 -104.55(15) . . . . ?
C8 N1 C17 C18 -133.25(17) . . . . ?
S1 N1 C17 C18 69.82(19) . . . . ?
C8 N1 C17 C16 42.99(18) . . . . ?
S1 N1 C17 C16 -113.93(13) . . . . ?
C14 C16 C17 C18 144.20(17) . . . . ?
C15 C16 C17 C18 -145.35(17) . . . . ?
C14 C16 C17 N1 -31.93(19) . . . . ?
C15 C16 C17 N1 38.5(2) . . . . ?
C16 C15 C19 O3 11.7(2) . . . . ?
C14 C15 C19 O3 -55.3(2) . . . . ?
C16 C15 C19 C20 -166.70(14) . . . . ?
C14 C15 C19 C20 126.32(15) . . . . ?
O3 C19 C20 C21 -46.1(2) . . . . ?
C15 C19 C20 C21 132.33(16) . . . . ?
O3 C19 C20 C25 134.57(18) . . . . ?
C15 C19 C20 C25 -47.0(2) . . . . ?
C25 C20 C21 C22 1.3(3) . . . . ?
C19 C20 C21 C22 -178.09(17) . . . . ?
C20 C21 C22 C23 -1.1(3) . . . . ?
C21 C22 C23 C24 0.1(3) . . . . ?
C22 C23 C24 C25 0.5(3) . . . . ?
C23 C24 C25 C20 -0.2(3) . . . . ?
C23 C24 C25 Cl1 -176.41(15) . . . . ?
C21 C20 C25 C24 -0.7(3) . . . . ?
C19 C20 C25 C24 178.68(17) . . . . ?
C21 C20 C25 Cl1 175.42(13) . . . . ?
C19 C20 C25 Cl1 -5.2(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
_geom_hbond_publ_flag
C6 H6 Cl1 0.95 2.96 3.7284(19) 139.1 3_666 yes
C18 H18B O1 0.95 2.58 3.500(2) 163.2 2_545 yes

_refine_diff_density_max         0.397
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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_shelxl_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc21fpls
_database_code_depnum_ccdc_archive 'CCDC 1889995'
loop_
_audit_author_name
_audit_author_address
lty
;CCDC?Nankai University
China
;
_audit_update_record             
;
2019-01-10 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H18 O3'
_chemical_formula_weight         366.39

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

_space_group_crystal_system      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                   9.5548(19)
_cell_length_b                   10.071(2)
_cell_length_c                   10.634(2)
_cell_angle_alpha                100.86(3)
_cell_angle_beta                 104.43(3)
_cell_angle_gamma                105.69(3)
_cell_volume                     917.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    2617
_cell_measurement_theta_min      2.0564
_cell_measurement_theta_max      27.8944

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7810
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11084
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.184
_diffrn_reflns_theta_max         27.895
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4356
_reflns_number_gt                3137
_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       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0960P)²] 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         4356
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1687
_refine_ls_wR_factor_gt          0.1485
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.002
_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 0.20289(13) 0.37807(12) 0.32505(13) 0.0290(3) Uani 1 1 d . . . . .
O2 O 0.27703(15) -0.08047(14) 0.48622(13) 0.0383(4) Uani 1 1 d . . . . .
O3 O 0.14301(14) 0.11215(13) 0.12538(12) 0.0304(3) Uani 1 1 d . . . . .
C1 C -0.0054(2) 0.2911(2) 0.3953(2) 0.0386(5) Uani 1 1 d . . . . .
H1A H -0.041544 0.363841 0.368509 0.046 Uiso 1 1 calc R U . . .
H1B H -0.062795 0.226093 0.432816 0.046 Uiso 1 1 calc R U . . .
C2 C 0.1248(2) 0.28043(18) 0.38022(18) 0.0277(4) Uani 1 1 d . . . . .
C3 C 0.1943(2) 0.17752(18) 0.42741(18) 0.0272(4) Uani 1 1 d . . . . .
H3 H 0.163479 0.146807 0.503461 0.033 Uiso 1 1 calc R U . . .
C4 C 0.35925(19) 0.19667(18) 0.43900(17) 0.0258(4) Uani 1 1 d . . . . .
H4 H 0.423765 0.182064 0.521535 0.031 Uiso 1 1 calc R U . . .
C5 C 0.4341(2) 0.31190(17) 0.38413(16) 0.0246(4) Uani 1 1 d . . . . .
C6 C 0.5862(2) 0.34085(18) 0.38598(18) 0.0281(4) Uani 1 1 d . . . . .
H6 H 0.643939 0.286465 0.423850 0.034 Uiso 1 1 calc R U . . .
C7 C 0.6543(2) 0.44791(19) 0.33332(19) 0.0305(4) Uani 1 1 d . . . . .
H7 H 0.758306 0.467798 0.336537 0.037 Uiso 1 1 calc R U . . .
C8 C 0.5692(2) 0.52529(18) 0.27617(18) 0.0307(4) Uani 1 1 d . . . . .
H8 H 0.614709 0.597366 0.238475 0.037 Uiso 1 1 calc R U . . .
C9 C 0.4178(2) 0.49872(19) 0.27331(18) 0.0283(4) Uani 1 1 d . . . . .
H9 H 0.359751 0.552335 0.234409 0.034 Uiso 1 1 calc R U . . .
C10 C 0.35296(18) 0.39271(17) 0.32813(17) 0.0239(4) Uani 1 1 d . . . . .
C11 C 0.23309(19) 0.06351(18) 0.33657(17) 0.0250(4) Uani 1 1 d . . . . .
C12 C 0.2040(2) -0.07462(19) 0.37638(18) 0.0275(4) Uani 1 1 d . . . . .
C13 C 0.0800(2) -0.20267(18) 0.27733(18) 0.0264(4) Uani 1 1 d . . . . .
C14 C 0.0903(2) -0.33954(19) 0.27242(18) 0.0291(4) Uani 1 1 d . . . . .
H14 H 0.172641 -0.350706 0.336206 0.035 Uiso 1 1 calc R U . . .
C15 C -0.0188(2) -0.4585(2) 0.17525(19) 0.0323(4) Uani 1 1 d . . . . .
H15 H -0.010202 -0.550913 0.170805 0.039 Uiso 1 1 calc R U . . .
C16 C -0.1406(2) -0.4423(2) 0.0845(2) 0.0360(5) Uani 1 1 d . . . . .
H16 H -0.215451 -0.524043 0.017641 0.043 Uiso 1 1 calc R U . . .
C17 C -0.1543(2) -0.3089(2) 0.0900(2) 0.0386(5) Uani 1 1 d . . . . .
H17 H -0.239078 -0.299207 0.027856 0.046 Uiso 1 1 calc R U . . .
C18 C -0.0447(2) -0.1887(2) 0.1862(2) 0.0329(4) Uani 1 1 d . . . . .
H18 H -0.054502 -0.096759 0.190087 0.040 Uiso 1 1 calc R U . . .
C19 C 0.21619(18) 0.05174(17) 0.19000(17) 0.0238(4) Uani 1 1 d . . . . .
C20 C 0.29858(19) -0.03632(17) 0.12974(17) 0.0247(4) Uani 1 1 d . . . . .
C21 C 0.2448(2) -0.09929(18) -0.00971(18) 0.0299(4) Uani 1 1 d . . . . .
H21 H 0.155896 -0.087946 -0.064195 0.036 Uiso 1 1 calc R U . . .
C22 C 0.3220(2) -0.1784(2) -0.0680(2) 0.0362(5) Uani 1 1 d . . . . .
H22 H 0.285744 -0.220965 -0.162815 0.043 Uiso 1 1 calc R U . . .
C23 C 0.4508(2) -0.1959(2) 0.0102(2) 0.0395(5) Uani 1 1 d . . . . .
H23 H 0.502599 -0.250378 -0.030947 0.047 Uiso 1 1 calc R U . . .
C24 C 0.5052(2) -0.1340(2) 0.1490(2) 0.0356(5) Uani 1 1 d . . . . .
H24 H 0.594172 -0.146048 0.202544 0.043 Uiso 1 1 calc R U . . .
C25 C 0.4292(2) -0.05457(19) 0.20920(19) 0.0291(4) Uani 1 1 d . . . . .
H25 H 0.465693 -0.012722 0.304103 0.035 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 C2 1.381(2) . ?
O1 C10 1.3926(19) . ?
O2 C12 1.223(2) . ?
O3 C19 1.216(2) . ?
C1 C2 1.323(2) . ?
C1 H1A 0.9500 . ?
C1 H1B 0.9500 . ?
C2 C3 1.473(2) . ?
C3 C4 1.506(2) . ?
C3 C11 1.543(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.488(2) . ?
C4 C11 1.536(2) . ?
C4 H4 1.0000 . ?
C5 C10 1.383(2) . ?
C5 C6 1.397(2) . ?
C6 C7 1.389(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(2) . ?
C9 H9 0.9500 . ?
C11 C12 1.504(2) . ?
C11 C19 1.505(2) . ?
C12 C13 1.489(3) . ?
C13 C18 1.394(2) . ?
C13 C14 1.400(2) . ?
C14 C15 1.382(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.376(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.494(2) . ?
C20 C21 1.398(2) . ?
C20 C25 1.400(2) . ?
C21 C22 1.387(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.378(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.390(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

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 C10 121.29(13) . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?
C1 C2 O1 117.26(16) . . ?
C1 C2 C3 123.50(17) . . ?
O1 C2 C3 119.10(14) . . ?
C2 C3 C4 119.86(14) . . ?
C2 C3 C11 124.75(15) . . ?
C4 C3 C11 60.49(11) . . ?
C2 C3 H3 113.8 . . ?
C4 C3 H3 113.8 . . ?
C11 C3 H3 113.8 . . ?
C5 C4 C3 115.08(14) . . ?
C5 C4 C11 116.96(14) . . ?
C3 C4 C11 60.95(11) . . ?
C5 C4 H4 117.3 . . ?
C3 C4 H4 117.3 . . ?
C11 C4 H4 117.3 . . ?
C10 C5 C6 118.14(16) . . ?
C10 C5 C4 120.23(15) . . ?
C6 C5 C4 121.63(15) . . ?
C7 C6 C5 121.03(16) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C6 119.39(16) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 120.67(16) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 118.92(16) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C5 C10 C9 121.84(16) . . ?
C5 C10 O1 123.60(15) . . ?
C9 C10 O1 114.54(15) . . ?
C12 C11 C19 116.49(15) . . ?
C12 C11 C4 117.27(15) . . ?
C19 C11 C4 116.30(14) . . ?
C12 C11 C3 112.03(14) . . ?
C19 C11 C3 123.77(15) . . ?
C4 C11 C3 58.56(11) . . ?
O2 C12 C13 121.68(16) . . ?
O2 C12 C11 121.39(16) . . ?
C13 C12 C11 116.92(15) . . ?
C18 C13 C14 119.12(17) . . ?
C18 C13 C12 121.15(16) . . ?
C14 C13 C12 119.71(16) . . ?
C15 C14 C13 120.33(17) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.70(18) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 120.67(19) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 120.09(18) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 120.05(18) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
O3 C19 C20 122.08(16) . . ?
O3 C19 C11 122.37(16) . . ?
C20 C19 C11 115.53(15) . . ?
C21 C20 C25 119.70(16) . . ?
C21 C20 C19 118.75(16) . . ?
C25 C20 C19 121.54(16) . . ?
C22 C21 C20 119.63(18) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C23 C22 C21 120.63(19) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 120.29(18) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C25 C24 C23 119.88(19) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C20 119.88(18) . . ?
C24 C25 H25 120.1 . . ?
C20 C25 H25 120.1 . . ?

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
C10 O1 C2 C1 167.98(16) . . . . ?
C10 O1 C2 C3 -7.9(2) . . . . ?
C1 C2 C3 C4 -164.37(17) . . . . ?
O1 C2 C3 C4 11.2(2) . . . . ?
C1 C2 C3 C11 122.7(2) . . . . ?
O1 C2 C3 C11 -61.7(2) . . . . ?
C2 C3 C4 C5 -7.3(2) . . . . ?
C11 C3 C4 C5 108.22(16) . . . . ?
C2 C3 C4 C11 -115.48(18) . . . . ?
C3 C4 C5 C10 0.2(2) . . . . ?
C11 C4 C5 C10 68.9(2) . . . . ?
C3 C4 C5 C6 -179.06(15) . . . . ?
C11 C4 C5 C6 -110.37(18) . . . . ?
C10 C5 C6 C7 0.1(2) . . . . ?
C4 C5 C6 C7 179.42(15) . . . . ?
C5 C6 C7 C8 -1.1(3) . . . . ?
C6 C7 C8 C9 1.2(3) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C6 C5 C10 C9 0.8(2) . . . . ?
C4 C5 C10 C9 -178.52(15) . . . . ?
C6 C5 C10 O1 -177.39(14) . . . . ?
C4 C5 C10 O1 3.3(2) . . . . ?
C8 C9 C10 C5 -0.7(3) . . . . ?
C8 C9 C10 O1 177.64(14) . . . . ?
C2 O1 C10 C5 0.6(2) . . . . ?
C2 O1 C10 C9 -177.70(15) . . . . ?
C5 C4 C11 C12 154.50(15) . . . . ?
C3 C4 C11 C12 -100.34(16) . . . . ?
C5 C4 C11 C19 10.0(2) . . . . ?
C3 C4 C11 C19 115.12(17) . . . . ?
C5 C4 C11 C3 -105.16(16) . . . . ?
C2 C3 C11 C12 -142.94(17) . . . . ?
C4 C3 C11 C12 109.38(16) . . . . ?
C2 C3 C11 C19 5.2(3) . . . . ?
C4 C3 C11 C19 -102.47(17) . . . . ?
C2 C3 C11 C4 107.68(18) . . . . ?
C19 C11 C12 O2 144.99(17) . . . . ?
C4 C11 C12 O2 0.5(2) . . . . ?
C3 C11 C12 O2 -64.4(2) . . . . ?
C19 C11 C12 C13 -36.4(2) . . . . ?
C4 C11 C12 C13 179.14(14) . . . . ?
C3 C11 C12 C13 114.26(17) . . . . ?
O2 C12 C13 C18 150.35(19) . . . . ?
C11 C12 C13 C18 -28.3(2) . . . . ?
O2 C12 C13 C14 -31.5(3) . . . . ?
C11 C12 C13 C14 149.87(16) . . . . ?
C18 C13 C14 C15 2.4(3) . . . . ?
C12 C13 C14 C15 -175.78(16) . . . . ?
C13 C14 C15 C16 -1.5(3) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C16 C17 C18 C13 0.2(3) . . . . ?
C14 C13 C18 C17 -1.7(3) . . . . ?
C12 C13 C18 C17 176.43(17) . . . . ?
C12 C11 C19 O3 132.00(17) . . . . ?
C4 C11 C19 O3 -83.2(2) . . . . ?
C3 C11 C19 O3 -14.9(2) . . . . ?
C12 C11 C19 C20 -49.4(2) . . . . ?
C4 C11 C19 C20 95.38(18) . . . . ?
C3 C11 C19 C20 163.69(15) . . . . ?
O3 C19 C20 C21 -26.3(2) . . . . ?
C11 C19 C20 C21 155.18(15) . . . . ?
O3 C19 C20 C25 152.52(16) . . . . ?
C11 C19 C20 C25 -26.0(2) . . . . ?
C25 C20 C21 C22 -0.4(3) . . . . ?
C19 C20 C21 C22 178.37(15) . . . . ?
C20 C21 C22 C23 0.2(3) . . . . ?
C21 C22 C23 C24 -0.1(3) . . . . ?
C22 C23 C24 C25 0.2(3) . . . . ?
C23 C24 C25 C20 -0.4(3) . . . . ?
C21 C20 C25 C24 0.5(3) . . . . ?
C19 C20 C25 C24 -178.23(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
_geom_hbond_publ_flag
C1 H1B O2 0.95 2.61 3.533(3) 164.1 2_556 yes

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.083

