# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_m10199_0m
_database_code_depnum_ccdc_archive 'CCDC 2245771'
loop_
_audit_author_name
_audit_author_address
li
;henu
China
;
_audit_update_record             
;
2023-03-02 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;
_audit_creation_date             2023-03-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 O4'
_chemical_formula_sum            'C19 H16 O4'
_chemical_formula_weight         308.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.9362(6)
_cell_length_b                   17.7920(10)
_cell_length_c                   8.2146(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.127(2)
_cell_angle_gamma                90
_cell_volume                     1519.04(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2563
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.779
_cell_measurement_theta_min      2.849
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.2627
_exptl_absorpt_correction_T_min  0.2238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1072 before and 0.0553 after correction. The Ratio of minimum to maximum transmission is 0.8519. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14415
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         1.959
_diffrn_ambient_temperature      296.3
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Helios multilayer optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_source            'Incoatc Ius 3.0 '
_diffrn_source_type              Microfocus
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2097
_reflns_number_total             2977
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2977
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0377P)²+0.4264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.1062
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.68366(13) 0.30105(8) 0.16090(17) 0.0296(3) Uani 1 1 d . . . . .
O2 O 0.48837(12) 0.38199(7) 0.38616(16) 0.0238(3) Uani 1 1 d . . . . .
O3 O 0.68523(13) 0.37521(8) 0.66116(16) 0.0276(3) Uani 1 1 d . . . . .
O4 O 0.82549(14) 0.34759(9) 0.51964(17) 0.0375(4) Uani 1 1 d . . . . .
C1 C 0.53844(19) 0.51272(11) 0.2468(2) 0.0273(5) Uani 1 1 d . . . . .
H1 H 0.460961 0.504081 0.268104 0.033 Uiso 1 1 calc R . . . .
C2 C 0.5601(2) 0.58076(12) 0.1778(3) 0.0336(5) Uani 1 1 d . . . . .
H2 H 0.496432 0.617471 0.152051 0.040 Uiso 1 1 calc R . . . .
C3 C 0.6746(2) 0.59445(12) 0.1472(3) 0.0343(5) Uani 1 1 d . . . . .
H3 H 0.688564 0.640367 0.101824 0.041 Uiso 1 1 calc R . . . .
C4 C 0.7684(2) 0.54008(12) 0.1838(3) 0.0366(5) Uani 1 1 d . . . . .
H4 H 0.846033 0.549426 0.163407 0.044 Uiso 1 1 calc R . . . .
C5 C 0.7484(2) 0.47142(12) 0.2510(3) 0.0324(5) Uani 1 1 d . . . . .
H5 H 0.811894 0.434636 0.274074 0.039 Uiso 1 1 calc R . . . .
C6 C 0.63301(18) 0.45764(11) 0.2837(2) 0.0231(4) Uani 1 1 d . . . . .
C7 C 0.61131(18) 0.38180(11) 0.3562(2) 0.0220(4) Uani 1 1 d . . . . .
C8 C 0.60032(19) 0.31702(11) 0.2250(2) 0.0241(4) Uani 1 1 d . . . . .
C9 C 0.47477(19) 0.28662(11) 0.1975(2) 0.0248(4) Uani 1 1 d . . . . .
H9 H 0.440910 0.245022 0.129973 0.030 Uiso 1 1 calc R . . . .
C10 C 0.41315(18) 0.32795(10) 0.2854(2) 0.0218(4) Uani 1 1 d . . . . .
C11 C 0.27994(18) 0.32639(11) 0.2868(2) 0.0219(4) Uani 1 1 d . . . . .
C12 C 0.19525(19) 0.27252(12) 0.1893(2) 0.0284(5) Uani 1 1 d . . . . .
H12 H 0.224532 0.237717 0.125515 0.034 Uiso 1 1 calc R . . . .
C13 C 0.0686(2) 0.27063(12) 0.1870(3) 0.0316(5) Uani 1 1 d . . . . .
H13 H 0.013165 0.234364 0.122486 0.038 Uiso 1 1 calc R . . . .
C14 C 0.02387(19) 0.32251(12) 0.2804(2) 0.0290(5) Uani 1 1 d . . . . .
H14 H -0.061485 0.321113 0.278846 0.035 Uiso 1 1 calc R . . . .
C15 C 0.10646(19) 0.37650(11) 0.3760(2) 0.0274(5) Uani 1 1 d . . . . .
H15 H 0.076204 0.411603 0.438151 0.033 Uiso 1 1 calc R . . . .
C16 C 0.23379(19) 0.37856(11) 0.3799(2) 0.0253(5) Uani 1 1 d . . . . .
H16 H 0.288774 0.414914 0.444800 0.030 Uiso 1 1 calc R . . . .
C17 C 0.71979(19) 0.36522(11) 0.5218(2) 0.0248(5) Uani 1 1 d . . . . .
C18 C 0.7879(2) 0.36391(12) 0.8237(2) 0.0322(5) Uani 1 1 d . . . . .
H18A H 0.839315 0.320667 0.814474 0.039 Uiso 1 1 calc R . . . .
H18B H 0.750313 0.354080 0.914164 0.039 Uiso 1 1 calc R . . . .
C19 C 0.8717(2) 0.43210(14) 0.8676(3) 0.0476(6) Uani 1 1 d . . . . .
H19A H 0.913837 0.439537 0.782362 0.071 Uiso 1 1 calc GR . . . .
H19B H 0.935110 0.425269 0.977562 0.071 Uiso 1 1 calc GR . . . .
H19C H 0.819906 0.475270 0.871148 0.071 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.219(2) . ?
O2 C7 1.440(2) . ?
O2 C10 1.365(2) . ?
O3 C17 1.324(2) . ?
O3 C18 1.467(2) . ?
O4 C17 1.203(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.388(3) . ?
C1 C6 1.388(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.373(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.391(3) . ?
C6 C7 1.523(3) . ?
C7 C8 1.557(3) . ?
C7 C17 1.530(3) . ?
C8 C9 1.427(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.348(3) . ?
C10 C11 1.461(3) . ?
C11 C12 1.399(3) . ?
C11 C16 1.393(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.384(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(3) . ?
C16 H16 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.495(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C10 O2 C7 108.25(14) . . ?
C17 O3 C18 115.17(15) . . ?
C2 C1 H1 120.2 . . ?
C2 C1 C6 119.7(2) . . ?
C6 C1 H1 120.2 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.7(2) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.5(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 119.48(19) . . ?
C1 C6 C7 120.98(18) . . ?
C5 C6 C7 119.53(17) . . ?
O2 C7 C6 109.39(15) . . ?
O2 C7 C8 104.18(14) . . ?
O2 C7 C17 110.83(15) . . ?
C6 C7 C8 111.88(15) . . ?
C6 C7 C17 110.27(15) . . ?
C17 C7 C8 110.14(15) . . ?
O1 C8 C7 124.35(18) . . ?
O1 C8 C9 130.94(18) . . ?
C9 C8 C7 104.66(16) . . ?
C8 C9 H9 125.5 . . ?
C10 C9 C8 108.98(17) . . ?
C10 C9 H9 125.5 . . ?
O2 C10 C11 115.01(16) . . ?
C9 C10 O2 113.68(17) . . ?
C9 C10 C11 131.28(18) . . ?
C12 C11 C10 119.52(17) . . ?
C16 C11 C10 121.62(17) . . ?
C16 C11 C12 118.84(18) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.51(19) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.19(19) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.82(19) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.39(19) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 H16 119.9 . . ?
C15 C16 C11 120.25(18) . . ?
C15 C16 H16 119.9 . . ?
O3 C17 C7 113.06(16) . . ?
O4 C17 O3 125.56(18) . . ?
O4 C17 C7 121.33(17) . . ?
O3 C18 H18A 109.6 . . ?
O3 C18 H18B 109.6 . . ?
O3 C18 C19 110.26(17) . . ?
H18A C18 H18B 108.1 . . ?
C19 C18 H18A 109.6 . . ?
C19 C18 H18B 109.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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 C8 C9 C10 -173.69(19) . . . . ?
O2 C7 C8 O1 176.50(17) . . . . ?
O2 C7 C8 C9 -1.21(18) . . . . ?
O2 C7 C17 O3 -17.6(2) . . . . ?
O2 C7 C17 O4 164.84(18) . . . . ?
O2 C10 C11 C12 -179.27(16) . . . . ?
O2 C10 C11 C16 2.4(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C1 C6 C7 O2 -3.7(2) . . . . ?
C1 C6 C7 C8 111.20(19) . . . . ?
C1 C6 C7 C17 -125.85(18) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C2 C1 C6 C7 -178.81(17) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C4 C5 C6 C7 179.54(18) . . . . ?
C5 C6 C7 O2 177.49(16) . . . . ?
C5 C6 C7 C8 -67.6(2) . . . . ?
C5 C6 C7 C17 55.4(2) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C6 C7 C8 O1 58.4(2) . . . . ?
C6 C7 C8 C9 -119.29(17) . . . . ?
C6 C7 C17 O3 103.71(18) . . . . ?
C6 C7 C17 O4 -73.9(2) . . . . ?
C7 O2 C10 C9 4.5(2) . . . . ?
C7 O2 C10 C11 -173.63(15) . . . . ?
C7 C8 C9 C10 3.8(2) . . . . ?
C8 C7 C17 O3 -132.33(17) . . . . ?
C8 C7 C17 O4 50.1(2) . . . . ?
C8 C9 C10 O2 -5.4(2) . . . . ?
C8 C9 C10 C11 172.36(18) . . . . ?
C9 C10 C11 C12 3.0(3) . . . . ?
C9 C10 C11 C16 -175.35(19) . . . . ?
C10 O2 C7 C6 118.01(15) . . . . ?
C10 O2 C7 C8 -1.76(18) . . . . ?
C10 O2 C7 C17 -120.19(16) . . . . ?
C10 C11 C12 C13 -179.16(18) . . . . ?
C10 C11 C16 C15 178.76(17) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C12 C11 C16 C15 0.4(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C11 0.2(3) . . . . ?
C16 C11 C12 C13 -0.7(3) . . . . ?
C17 O3 C18 C19 79.9(2) . . . . ?
C17 C7 C8 O1 -64.6(2) . . . . ?
C17 C7 C8 C9 117.69(17) . . . . ?
C18 O3 C17 O4 0.6(3) . . . . ?
C18 O3 C17 C7 -176.89(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_m12075_0m
_database_code_depnum_ccdc_archive 'CCDC 2297295'
loop_
_audit_author_name
_audit_author_address
'li pan'
;henu
China
;
_audit_update_record             
;
2023-09-25 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;
_audit_creation_date             2023-09-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H22 O5 S'
_chemical_formula_sum            'C20 H22 O5 S'
_chemical_formula_weight         374.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.549(3)
_cell_length_b                   10.8252(14)
_cell_length_c                   17.856(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.929(4)
_cell_angle_gamma                90
_cell_volume                     3807.4(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4488
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.511
_cell_measurement_theta_min      2.496
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.0479
_exptl_absorpt_correction_T_min  0.0252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1166 before and 0.0607 after correction. The Ratio of minimum to maximum transmission is 0.5261. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20858
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.068
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Helios multilayer optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_source            'Incoatc Ius 3.0 '
_diffrn_source_type              Microfocus
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2864
_reflns_number_total             3739
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3739
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0387P)²+3.6759P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.1089
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.c Me refined with riding coordinates:
 C7(H7A,H7B,H7C)
2.d Aromatic/amide H refined with riding coordinates:
 C14(H14), C8(H8), C3(H3), C5(H5), C2(H2), C15(H15), C18(H18), C6(H6),
 C16(H16), C17(H17)
2.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.61235(3) 0.88685(5) 0.75134(3) 0.03680(16) Uani 1 1 d . . . . .
O3 O 0.48944(7) 0.62546(13) 0.60746(9) 0.0369(3) Uani 1 1 d . . . . .
O4 O 0.49630(7) 0.71342(14) 0.47040(10) 0.0417(4) Uani 1 1 d . . . . .
O1 O 0.59368(8) 1.01528(14) 0.74173(10) 0.0455(4) Uani 1 1 d . . . . .
O5 O 0.41552(8) 0.85499(14) 0.45392(10) 0.0474(4) Uani 1 1 d . . . . .
O2 O 0.62540(8) 0.82751(16) 0.82863(10) 0.0479(4) Uani 1 1 d . . . . .
C13 C 0.37549(10) 0.60534(19) 0.50984(13) 0.0341(5) Uani 1 1 d . . . . .
C12 C 0.44775(10) 0.76550(19) 0.48733(13) 0.0348(5) Uani 1 1 d . . . . .
C11 C 0.43263(10) 0.69567(19) 0.55200(13) 0.0343(5) Uani 1 1 d . . . . .
H11 H 0.418085 0.755887 0.584203 0.041 Uiso 1 1 calc R . . . .
C4 C 0.68577(10) 0.86838(19) 0.73165(13) 0.0337(5) Uani 1 1 d . . . . .
C9 C 0.54147(10) 0.6866(2) 0.66726(13) 0.0354(5) Uani 1 1 d . . . . .
C14 C 0.31197(10) 0.6274(2) 0.50958(14) 0.0366(5) Uani 1 1 d . . . . .
H14 H 0.305173 0.696585 0.538134 0.044 Uiso 1 1 calc R . . . .
C8 C 0.54738(10) 0.8095(2) 0.67234(13) 0.0355(5) Uani 1 1 d . . . . .
H8 H 0.514345 0.857529 0.630592 0.043 Uiso 1 1 calc R . . . .
C3 C 0.73782(11) 0.7898(2) 0.77934(14) 0.0407(5) Uani 1 1 d . . . . .
H3 H 0.735196 0.747245 0.824503 0.049 Uiso 1 1 calc R . . . .
C5 C 0.68988(11) 0.9322(2) 0.66648(15) 0.0407(5) Uani 1 1 d . . . . .
H5 H 0.654569 0.986868 0.634498 0.049 Uiso 1 1 calc R . . . .
C2 C 0.79372(11) 0.7741(2) 0.76020(15) 0.0438(6) Uani 1 1 d . . . . .
H2 H 0.829406 0.720545 0.792748 0.053 Uiso 1 1 calc R . . . .
C15 C 0.25839(11) 0.5484(2) 0.46757(15) 0.0422(5) Uani 1 1 d . . . . .
H15 H 0.214682 0.564315 0.466474 0.051 Uiso 1 1 calc R . . . .
C1 C 0.79829(11) 0.8353(2) 0.69437(15) 0.0414(5) Uani 1 1 d . . . . .
C18 C 0.38550(12) 0.5020(2) 0.46974(16) 0.0445(6) Uani 1 1 d . . . . .
H18 H 0.429057 0.485828 0.470427 0.053 Uiso 1 1 calc R . . . .
C19 C 0.51089(13) 0.7706(2) 0.40481(16) 0.0480(6) Uani 1 1 d . . . . .
H19A H 0.468500 0.804772 0.362656 0.058 Uiso 1 1 calc R . . . .
H19B H 0.528449 0.707202 0.378447 0.058 Uiso 1 1 calc R . . . .
C6 C 0.74609(12) 0.9153(2) 0.64863(16) 0.0454(6) Uani 1 1 d . . . . .
H6 H 0.749110 0.959222 0.604171 0.054 Uiso 1 1 calc R . . . .
C16 C 0.26854(12) 0.4470(2) 0.42752(16) 0.0489(6) Uani 1 1 d . . . . .
H16 H 0.231723 0.393173 0.398707 0.059 Uiso 1 1 calc R . . . .
C10 C 0.58837(12) 0.5937(2) 0.72395(16) 0.0508(6) Uani 1 1 d . . . . .
H10A H 0.571644 0.569979 0.765404 0.076 Uiso 1 1 calc GR . . . .
H10B H 0.633849 0.629578 0.750928 0.076 Uiso 1 1 calc GR . . . .
H10C H 0.590428 0.520498 0.692726 0.076 Uiso 1 1 calc GR . . . .
C17 C 0.33208(13) 0.4229(2) 0.42894(17) 0.0527(6) Uani 1 1 d . . . . .
H17 H 0.338960 0.352080 0.401854 0.063 Uiso 1 1 calc R . . . .
C7 C 0.85771(13) 0.8138(2) 0.67157(19) 0.0560(7) Uani 1 1 d . . . . .
H7A H 0.852322 0.864605 0.623878 0.084 Uiso 1 1 calc R . . . .
H7B H 0.899935 0.836588 0.717790 0.084 Uiso 1 1 calc R . . . .
H7C H 0.859434 0.726437 0.658254 0.084 Uiso 1 1 calc R . . . .
C20 C 0.56226(14) 0.8719(2) 0.43828(18) 0.0578(7) Uani 1 1 d . . . . .
H20A H 0.570780 0.909849 0.393498 0.087 Uiso 1 1 calc GR . . . .
H20B H 0.604682 0.837605 0.478763 0.087 Uiso 1 1 calc GR . . . .
H20C H 0.544886 0.934608 0.464437 0.087 Uiso 1 1 calc GR . . . .


_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 O1 1.4381(17) . ?
S1 O2 1.4428(17) . ?
S1 C4 1.766(2) . ?
S1 C8 1.746(2) . ?
O3 C11 1.440(2) . ?
O3 C9 1.365(3) . ?
O4 C12 1.327(2) . ?
O4 C19 1.467(3) . ?
O5 C12 1.200(2) . ?
C13 C11 1.512(3) . ?
C13 C14 1.388(3) . ?
C13 C18 1.391(3) . ?
C12 C11 1.522(3) . ?
C4 C3 1.390(3) . ?
C4 C5 1.387(3) . ?
C9 C8 1.336(3) . ?
C9 C10 1.492(3) . ?
C14 C15 1.388(3) . ?
C3 C2 1.389(3) . ?
C5 C6 1.384(3) . ?
C2 C1 1.387(3) . ?
C15 C16 1.375(3) . ?
C1 C6 1.392(3) . ?
C1 C7 1.511(3) . ?
C18 C17 1.381(3) . ?
C19 C20 1.500(3) . ?
C16 C17 1.384(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 118.76(11) . . ?
O1 S1 C4 108.40(10) . . ?
O1 S1 C8 105.87(10) . . ?
O2 S1 C4 107.29(10) . . ?
O2 S1 C8 109.91(10) . . ?
C8 S1 C4 105.93(10) . . ?
C9 O3 C11 118.79(16) . . ?
C12 O4 C19 116.54(17) . . ?
C14 C13 C11 119.55(19) . . ?
C14 C13 C18 119.7(2) . . ?
C18 C13 C11 120.74(19) . . ?
O4 C12 C11 113.15(17) . . ?
O5 C12 O4 125.5(2) . . ?
O5 C12 C11 121.28(19) . . ?
O3 C11 C13 107.13(16) . . ?
O3 C11 C12 113.58(16) . . ?
C13 C11 C12 108.97(17) . . ?
C3 C4 S1 120.85(17) . . ?
C5 C4 S1 118.55(16) . . ?
C5 C4 C3 120.6(2) . . ?
O3 C9 C10 108.62(18) . . ?
C8 C9 O3 124.13(19) . . ?
C8 C9 C10 127.2(2) . . ?
C15 C14 C13 119.9(2) . . ?
C9 C8 S1 123.75(17) . . ?
C2 C3 C4 119.3(2) . . ?
C6 C5 C4 119.1(2) . . ?
C1 C2 C3 121.1(2) . . ?
C16 C15 C14 120.0(2) . . ?
C2 C1 C6 118.4(2) . . ?
C2 C1 C7 121.0(2) . . ?
C6 C1 C7 120.6(2) . . ?
C17 C18 C13 120.0(2) . . ?
O4 C19 C20 110.7(2) . . ?
C5 C6 C1 121.5(2) . . ?
C15 C16 C17 120.4(2) . . ?
C18 C17 C16 120.0(2) . . ?

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
S1 C4 C3 C2 177.67(17) . . . . ?
S1 C4 C5 C6 -177.78(17) . . . . ?
O3 C9 C8 S1 177.39(16) . . . . ?
O4 C12 C11 O3 26.6(2) . . . . ?
O4 C12 C11 C13 -92.8(2) . . . . ?
O1 S1 C4 C3 139.58(18) . . . . ?
O1 S1 C4 C5 -41.7(2) . . . . ?
O1 S1 C8 C9 -170.27(19) . . . . ?
O5 C12 C11 O3 -156.67(19) . . . . ?
O5 C12 C11 C13 84.0(2) . . . . ?
O2 S1 C4 C3 10.2(2) . . . . ?
O2 S1 C4 C5 -171.05(17) . . . . ?
O2 S1 C8 C9 -40.9(2) . . . . ?
C13 C14 C15 C16 1.2(3) . . . . ?
C13 C18 C17 C16 0.4(4) . . . . ?
C12 O4 C19 C20 87.5(2) . . . . ?
C11 O3 C9 C8 -8.2(3) . . . . ?
C11 O3 C9 C10 171.41(18) . . . . ?
C11 C13 C14 C15 176.8(2) . . . . ?
C11 C13 C18 C17 -177.6(2) . . . . ?
C4 S1 C8 C9 74.7(2) . . . . ?
C4 C3 C2 C1 -0.1(3) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C9 O3 C11 C13 -164.08(17) . . . . ?
C9 O3 C11 C12 75.5(2) . . . . ?
C14 C13 C11 O3 127.9(2) . . . . ?
C14 C13 C11 C12 -108.9(2) . . . . ?
C14 C13 C18 C17 0.9(4) . . . . ?
C14 C15 C16 C17 0.1(4) . . . . ?
C8 S1 C4 C3 -107.18(19) . . . . ?
C8 S1 C4 C5 71.58(19) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C3 C2 C1 C6 1.4(3) . . . . ?
C3 C2 C1 C7 -177.4(2) . . . . ?
C5 C4 C3 C2 -1.1(3) . . . . ?
C2 C1 C6 C5 -1.4(3) . . . . ?
C15 C16 C17 C18 -1.0(4) . . . . ?
C18 C13 C11 O3 -53.6(3) . . . . ?
C18 C13 C11 C12 69.6(3) . . . . ?
C18 C13 C14 C15 -1.7(3) . . . . ?
C19 O4 C12 O5 -0.4(3) . . . . ?
C19 O4 C12 C11 176.18(18) . . . . ?
C10 C9 C8 S1 -2.2(3) . . . . ?
C7 C1 C6 C5 177.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_m12242_0m
_database_code_depnum_ccdc_archive 'CCDC 2300405'
loop_
_audit_author_name
_audit_author_address
'li pan'
;henu
China
;
_audit_update_record             
;
2023-10-11 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;
_audit_creation_date             2023-10-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H22 O4'
_chemical_formula_sum            'C25 H22 O4'
_chemical_formula_weight         386.42
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.2833(18)
_cell_length_b                   10.038(2)
_cell_length_c                   20.688(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.406(7)
_cell_angle_gamma                90
_cell_volume                     2112.7(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4623
_cell_measurement_temperature    150
_cell_measurement_theta_max      24.774
_cell_measurement_theta_min      2.260
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.2627
_exptl_absorpt_correction_T_min  0.2103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1095 before and 0.0869 after correction. The Ratio of minimum to maximum transmission is 0.8005. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_av_unetI/netI     0.0761
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20567
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         1.990
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Helios multilayer optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_source            'Incoatc Ius 3.0 '
_diffrn_source_type              Microfocus
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2702
_reflns_number_total             4160
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4160
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0604
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0623P)²+0.7084P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1480
_refine_ls_wR_factor_ref         0.1723
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C24) \\sim Ueq, Uanis(C25) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25)
3.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.36752(14) 0.62362(16) 0.82657(7) 0.0381(4) Uani 1 1 d . . . . .
O2 O 0.62758(16) 0.59068(17) 0.73588(8) 0.0487(5) Uani 1 1 d . . . . .
O3 O 0.52575(18) 0.42565(18) 0.78186(9) 0.0554(5) Uani 1 1 d . . . . .
O4 O 0.07949(19) 0.5565(3) 0.66050(9) 0.0755(7) Uani 1 1 d . . . . .
C1 C 0.4976(2) 0.6548(2) 0.81373(10) 0.0333(5) Uani 1 1 d . . . . .
H1 H 0.495863 0.739099 0.787896 0.040 Uiso 1 1 calc R . . . .
C2 C 0.5829(2) 0.6730(2) 0.87930(10) 0.0345(5) Uani 1 1 d . . . . .
C3 C 0.5498(2) 0.5414(3) 0.77600(11) 0.0383(5) Uani 1 1 d . . . . .
C4 C 0.2690(2) 0.6129(2) 0.77477(11) 0.0356(5) Uani 1 1 d . . . . .
C5 C 0.2132(2) 0.6528(2) 0.58992(11) 0.0415(6) Uani 1 1 d . . . . .
C6 C 0.2846(2) 0.6359(3) 0.71233(11) 0.0423(6) Uani 1 1 d . . . . .
H6 H 0.366736 0.670490 0.704295 0.051 Uiso 1 1 calc R . . . .
C7 C 0.1460(2) 0.5771(3) 0.79994(11) 0.0439(6) Uani 1 1 d . . . . .
C8 C 0.1841(2) 0.6114(3) 0.65594(11) 0.0458(6) Uani 1 1 d . . . . .
C9 C 0.6481(2) 0.7915(3) 0.89406(12) 0.0470(6) Uani 1 1 d . . . . .
H9 H 0.638308 0.862493 0.863379 0.056 Uiso 1 1 calc R . . . .
C10 C 0.5968(2) 0.5705(3) 0.92490(12) 0.0460(6) Uani 1 1 d . . . . .
H10 H 0.551359 0.488824 0.915365 0.055 Uiso 1 1 calc R . . . .
C11 C 0.6767(3) 0.5872(3) 0.98412(13) 0.0543(7) Uani 1 1 d . . . . .
H11 H 0.686366 0.516865 1.015173 0.065 Uiso 1 1 calc R . . . .
C12 C 0.1091(3) 0.6537(3) 0.53857(13) 0.0578(7) Uani 1 1 d . . . . .
H12 H 0.023333 0.630028 0.546411 0.069 Uiso 1 1 calc R . . . .
C13 C 0.7422(3) 0.7052(3) 0.99816(13) 0.0570(7) Uani 1 1 d . . . . .
H13 H 0.797497 0.716113 1.038805 0.068 Uiso 1 1 calc R . . . .
C14 C 0.3367(3) 0.6855(3) 0.57686(13) 0.0580(7) Uani 1 1 d . . . . .
H14 H 0.408951 0.685574 0.611194 0.070 Uiso 1 1 calc R . . . .
C15 C 0.7282(3) 0.8073(3) 0.95374(15) 0.0614(8) Uani 1 1 d . . . . .
H15 H 0.773215 0.888994 0.963755 0.074 Uiso 1 1 calc R . . . .
C16 C 0.6908(3) 0.4946(3) 0.69750(15) 0.0656(8) Uani 1 1 d . . . . .
H16A H 0.624737 0.432861 0.674387 0.079 Uiso 1 1 calc R . . . .
H16B H 0.756978 0.441864 0.726310 0.079 Uiso 1 1 calc R . . . .
C17 C 0.0478(3) 0.6712(4) 0.79907(15) 0.0642(8) Uani 1 1 d . . . . .
H17 H 0.056895 0.755978 0.779808 0.077 Uiso 1 1 calc R . . . .
C18 C 0.2517(4) 0.7202(3) 0.46409(14) 0.0740(9) Uani 1 1 d . . . . .
H18 H 0.265042 0.743413 0.421041 0.089 Uiso 1 1 calc R . . . .
C19 C 0.1298(4) 0.6888(3) 0.47644(14) 0.0716(9) Uani 1 1 d . . . . .
H19 H 0.057780 0.690977 0.441996 0.086 Uiso 1 1 calc R . . . .
C20 C 0.3564(3) 0.7184(3) 0.51382(14) 0.0727(9) Uani 1 1 d . . . . .
H20 H 0.442087 0.739745 0.505018 0.087 Uiso 1 1 calc R . . . .
C21 C 0.1332(3) 0.4552(4) 0.82801(17) 0.0798(11) Uani 1 1 d . . . . .
H21 H 0.201838 0.391435 0.829570 0.096 Uiso 1 1 calc R . . . .
C22 C 0.7546(4) 0.5715(4) 0.65011(19) 0.0930(12) Uani 1 1 d . . . . .
H22A H 0.687731 0.621107 0.621062 0.139 Uiso 1 1 calc GR . . . .
H22B H 0.800567 0.510512 0.624202 0.139 Uiso 1 1 calc GR . . . .
H22C H 0.817790 0.634109 0.673571 0.139 Uiso 1 1 calc GR . . . .
C23 C -0.0638(3) 0.6415(6) 0.82637(19) 0.0978(15) Uani 1 1 d . . . . .
H23 H -0.131790 0.705742 0.825725 0.117 Uiso 1 1 calc R . . . .
C24 C -0.0758(4) 0.5202(7) 0.85412(19) 0.1124(17) Uani 1 1 d . U . . .
H24 H -0.151645 0.500984 0.873760 0.135 Uiso 1 1 calc R . . . .
C25 C 0.0203(4) 0.4248(5) 0.8541(2) 0.1117(16) Uani 1 1 d . U . . .
H25 H 0.009291 0.338967 0.871851 0.134 Uiso 1 1 calc R . . . .


_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 C1 1.436(2) . ?
O1 C4 1.367(3) . ?
O2 C3 1.330(3) . ?
O2 C16 1.461(3) . ?
O3 C3 1.198(3) . ?
O4 C8 1.224(3) . ?
C1 H1 1.0000 . ?
C1 C2 1.515(3) . ?
C1 C3 1.522(3) . ?
C2 C9 1.378(3) . ?
C2 C10 1.389(3) . ?
C4 C6 1.345(3) . ?
C4 C7 1.481(3) . ?
C5 C8 1.499(3) . ?
C5 C12 1.393(3) . ?
C5 C14 1.377(4) . ?
C6 H6 0.9500 . ?
C6 C8 1.462(3) . ?
C7 C17 1.381(4) . ?
C7 C21 1.369(4) . ?
C9 H9 0.9500 . ?
C9 C15 1.389(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(3) . ?
C11 H11 0.9500 . ?
C11 C13 1.372(4) . ?
C12 H12 0.9500 . ?
C12 C19 1.379(4) . ?
C13 H13 0.9500 . ?
C13 C15 1.370(4) . ?
C14 H14 0.9500 . ?
C14 C20 1.389(4) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C22 1.475(4) . ?
C17 H17 0.9500 . ?
C17 C23 1.384(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.352(5) . ?
C18 C20 1.376(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C21 C25 1.384(5) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23 0.9500 . ?
C23 C24 1.360(7) . ?
C24 H24 0.9500 . ?
C24 C25 1.376(7) . ?
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
C4 O1 C1 118.42(16) . . ?
C3 O2 C16 116.7(2) . . ?
O1 C1 H1 109.8 . . ?
O1 C1 C2 107.08(16) . . ?
O1 C1 C3 109.88(18) . . ?
C2 C1 H1 109.8 . . ?
C2 C1 C3 110.39(17) . . ?
C3 C1 H1 109.8 . . ?
C9 C2 C1 120.1(2) . . ?
C9 C2 C10 119.4(2) . . ?
C10 C2 C1 120.5(2) . . ?
O2 C3 C1 109.4(2) . . ?
O3 C3 O2 125.2(2) . . ?
O3 C3 C1 125.5(2) . . ?
O1 C4 C7 108.46(18) . . ?
C6 C4 O1 124.1(2) . . ?
C6 C4 C7 127.4(2) . . ?
C12 C5 C8 117.6(2) . . ?
C14 C5 C8 123.9(2) . . ?
C14 C5 C12 118.5(2) . . ?
C4 C6 H6 117.7 . . ?
C4 C6 C8 124.6(2) . . ?
C8 C6 H6 117.7 . . ?
C17 C7 C4 119.3(2) . . ?
C21 C7 C4 120.4(2) . . ?
C21 C7 C17 120.1(3) . . ?
O4 C8 C5 119.3(2) . . ?
O4 C8 C6 122.7(2) . . ?
C6 C8 C5 117.9(2) . . ?
C2 C9 H9 120.0 . . ?
C2 C9 C15 120.1(2) . . ?
C15 C9 H9 120.0 . . ?
C2 C10 H10 120.0 . . ?
C11 C10 C2 120.1(2) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.9 . . ?
C13 C11 C10 120.1(2) . . ?
C13 C11 H11 119.9 . . ?
C5 C12 H12 119.8 . . ?
C19 C12 C5 120.4(3) . . ?
C19 C12 H12 119.8 . . ?
C11 C13 H13 119.9 . . ?
C15 C13 C11 120.2(2) . . ?
C15 C13 H13 119.9 . . ?
C5 C14 H14 119.8 . . ?
C5 C14 C20 120.4(3) . . ?
C20 C14 H14 119.8 . . ?
C9 C15 H15 119.9 . . ?
C13 C15 C9 120.1(3) . . ?
C13 C15 H15 119.9 . . ?
O2 C16 H16A 110.3 . . ?
O2 C16 H16B 110.3 . . ?
O2 C16 C22 107.0(3) . . ?
H16A C16 H16B 108.6 . . ?
C22 C16 H16A 110.3 . . ?
C22 C16 H16B 110.3 . . ?
C7 C17 H17 120.1 . . ?
C7 C17 C23 119.7(4) . . ?
C23 C17 H17 120.1 . . ?
C19 C18 H18 120.0 . . ?
C19 C18 C20 120.1(3) . . ?
C20 C18 H18 120.0 . . ?
C12 C19 H19 119.7 . . ?
C18 C19 C12 120.6(3) . . ?
C18 C19 H19 119.7 . . ?
C14 C20 H20 120.0 . . ?
C18 C20 C14 120.0(3) . . ?
C18 C20 H20 120.0 . . ?
C7 C21 H21 120.0 . . ?
C7 C21 C25 120.0(4) . . ?
C25 C21 H21 120.0 . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C17 C23 H23 120.1 . . ?
C24 C23 C17 119.8(4) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 119.6 . . ?
C23 C24 C25 120.9(3) . . ?
C25 C24 H24 119.6 . . ?
C21 C25 H25 120.3 . . ?
C24 C25 C21 119.4(4) . . ?
C24 C25 H25 120.3 . . ?

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 C9 -121.8(2) . . . . ?
O1 C1 C2 C10 58.6(3) . . . . ?
O1 C1 C3 O2 147.19(17) . . . . ?
O1 C1 C3 O3 -33.5(3) . . . . ?
O1 C4 C6 C8 173.2(2) . . . . ?
O1 C4 C7 C17 108.2(2) . . . . ?
O1 C4 C7 C21 -67.2(3) . . . . ?
C1 O1 C4 C6 -3.3(3) . . . . ?
C1 O1 C4 C7 178.54(19) . . . . ?
C1 C2 C9 C15 -178.9(2) . . . . ?
C1 C2 C10 C11 178.8(2) . . . . ?
C2 C1 C3 O2 -94.9(2) . . . . ?
C2 C1 C3 O3 84.4(3) . . . . ?
C2 C9 C15 C13 -0.2(4) . . . . ?
C2 C10 C11 C13 0.2(4) . . . . ?
C3 O2 C16 C22 171.5(3) . . . . ?
C3 C1 C2 C9 118.6(2) . . . . ?
C3 C1 C2 C10 -61.0(3) . . . . ?
C4 O1 C1 C2 174.83(18) . . . . ?
C4 O1 C1 C3 -65.3(2) . . . . ?
C4 C6 C8 O4 -6.4(4) . . . . ?
C4 C6 C8 C5 175.1(2) . . . . ?
C4 C7 C17 C23 -175.8(3) . . . . ?
C4 C7 C21 C25 177.0(3) . . . . ?
C5 C12 C19 C18 1.4(5) . . . . ?
C5 C14 C20 C18 0.9(5) . . . . ?
C6 C4 C7 C17 -69.9(4) . . . . ?
C6 C4 C7 C21 114.6(3) . . . . ?
C7 C4 C6 C8 -8.9(4) . . . . ?
C7 C17 C23 C24 0.3(5) . . . . ?
C7 C21 C25 C24 -2.9(6) . . . . ?
C8 C5 C12 C19 -179.0(3) . . . . ?
C8 C5 C14 C20 177.7(3) . . . . ?
C9 C2 C10 C11 -0.8(4) . . . . ?
C10 C2 C9 C15 0.8(4) . . . . ?
C10 C11 C13 C15 0.4(4) . . . . ?
C11 C13 C15 C9 -0.4(5) . . . . ?
C12 C5 C8 O4 13.8(4) . . . . ?
C12 C5 C8 C6 -167.7(2) . . . . ?
C12 C5 C14 C20 -0.1(4) . . . . ?
C14 C5 C8 O4 -164.0(3) . . . . ?
C14 C5 C8 C6 14.5(4) . . . . ?
C14 C5 C12 C19 -1.0(4) . . . . ?
C16 O2 C3 O3 -1.7(4) . . . . ?
C16 O2 C3 C1 177.6(2) . . . . ?
C17 C7 C21 C25 1.6(5) . . . . ?
C17 C23 C24 C25 -1.5(6) . . . . ?
C19 C18 C20 C14 -0.5(5) . . . . ?
C20 C18 C19 C12 -0.6(5) . . . . ?
C21 C7 C17 C23 -0.3(4) . . . . ?
C23 C24 C25 C21 2.8(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
