# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_fyc-2-2-1012
_database_code_depnum_ccdc_archive 'CCDC 2056365'
loop_
_audit_author_name
_audit_author_address
'Han Wen-Yong'
;Zunyi Medical University
China
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;
_audit_creation_date             2019-10-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C4.25 H3.5 O0.75)'
_chemical_formula_sum            'C17 H14 O3'
_chemical_formula_weight         266.28
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   24.0388(11)
_cell_length_b                   11.3009(4)
_cell_length_c                   36.9112(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     10027.3(7)
_cell_formula_units_Z            32
_cell_measurement_reflns_used    9249
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.0440
_cell_measurement_theta_min      2.0900
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             4480
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            32274
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.022
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5368
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00  52.00   0.30    3.50    --   11.74 -19.00  60.00  400
  2  ω      9.00  37.80   0.30    3.50    --   11.74 -99.00 -30.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0218413000
_diffrn_orient_matrix_UB_12      0.0227498000
_diffrn_orient_matrix_UB_13      -0.0108910000
_diffrn_orient_matrix_UB_21      0.0082902000
_diffrn_orient_matrix_UB_22      0.0585057000
_diffrn_orient_matrix_UB_23      0.0043615000
_diffrn_orient_matrix_UB_31      0.0179976000
_diffrn_orient_matrix_UB_32      0.0006719000
_diffrn_orient_matrix_UB_33      -0.0152273000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7058
_reflns_number_total             8832
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     721
_refine_ls_number_reflns         8832
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      1.016
_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)+(0.0644P)²+9.3472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1474
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C10(H10), C14(H14), C16(H16), C29(H29), C32(H32), C30(H30),
 C47(H47), C49(H49), C46(H46), C52(H52), C53(H53), C28(H28), C58(H58), C45(H45),
  C54(H54)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C12(H12A,H12B), C34(H34A,H34B), C13(H13A,H13B), C33(H33A,
 H33B), C50(H50A,H50B), C51(H51A,H51B), C31(H31A,H31B), C48(H48A,H48B),
 C56(H56A,H56B), C57(H57A,H57B), C55(H55A,H55B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C24(H24), C22(H22), C68(H68), C65(H65), C35(H35), C67(H67),
 C36(H36), C66(H66), C9(H9), C23(H23), C6(H6), C37(H37), C7(H7), C38(H38),
 C8(H8)
;
_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 0.33178(6) 0.74011(14) 0.54532(4) 0.0188(4) Uani 1 1 d . . . . .
O5 O 0.59487(6) 0.81205(14) 0.58809(4) 0.0198(4) Uani 1 1 d . . . . .
O12 O 0.89843(7) 0.59713(15) 0.86273(4) 0.0238(4) Uani 1 1 d . . . . .
O7 O 0.66252(7) 0.69455(15) 0.67429(4) 0.0228(4) Uani 1 1 d . . . . .
O4 O 0.45126(7) 0.83104(15) 0.52687(4) 0.0230(4) Uani 1 1 d . . . . .
O3 O 0.39623(7) 0.58803(14) 0.49840(4) 0.0251(4) Uani 1 1 d . . . . .
O2 O 0.24441(7) 0.99493(15) 0.48829(4) 0.0252(4) Uani 1 1 d . . . . .
O9 O 0.74727(7) 0.45698(16) 0.73938(4) 0.0292(4) Uani 1 1 d . . . . .
O11 O 1.04314(7) 0.55827(17) 0.80298(4) 0.0297(4) Uani 1 1 d . . . . .
O6 O 0.69015(7) 0.74719(19) 0.54543(5) 0.0353(5) Uani 1 1 d . . . . .
O8 O 0.61008(8) 0.87990(17) 0.71571(5) 0.0368(5) Uani 1 1 d . . . . .
O10 O 0.80561(8) 0.6595(2) 0.81901(5) 0.0425(5) Uani 1 1 d . . . . .
C20 C 0.54463(9) 0.84064(19) 0.60424(6) 0.0164(5) Uani 1 1 d . . . . .
C62 C 1.00044(10) 0.5699(2) 0.82072(6) 0.0215(5) Uani 1 1 d . . . . .
C40 C 0.69193(10) 0.6012(2) 0.65904(6) 0.0194(5) Uani 1 1 d . . . . .
C19 C 0.49514(9) 0.84744(19) 0.58453(6) 0.0163(5) Uani 1 1 d . . . . .
C63 C 0.99803(10) 0.5585(2) 0.86055(6) 0.0194(5) Uani 1 1 d . . . . .
C4 C 0.29861(9) 0.8215(2) 0.56340(6) 0.0182(5) Uani 1 1 d . . . . .
C64 C 0.94828(10) 0.5720(2) 0.87972(6) 0.0193(5) Uani 1 1 d . . . . .
C18 C 0.49384(9) 0.8240(2) 0.54498(6) 0.0176(5) Uani 1 1 d . . . . .
C3 C 0.26857(9) 0.9086(2) 0.54513(6) 0.0177(5) Uani 1 1 d . . . . .
C5 C 0.33358(9) 0.7513(2) 0.50888(6) 0.0167(5) Uani 1 1 d . . . . .
C1 C 0.30661(9) 0.8308(2) 0.48825(6) 0.0166(5) Uani 1 1 d . . . . .
C17 C 0.36816(9) 0.6696(2) 0.48710(6) 0.0182(5) Uani 1 1 d . . . . .
C21 C 0.54653(10) 0.8615(2) 0.64118(6) 0.0209(5) Uani 1 1 d . . . . .
H21 H 0.580010 0.856718 0.653724 0.025 Uiso 1 1 calc R U . . .
C24 C 0.44643(10) 0.8756(2) 0.60350(6) 0.0200(5) Uani 1 1 d . . . . .
H24 H 0.412849 0.880628 0.591080 0.024 Uiso 1 1 calc R U . . .
C22 C 0.49794(10) 0.8893(2) 0.65901(6) 0.0228(5) Uani 1 1 d . . . . .
H22 H 0.498634 0.903825 0.683806 0.027 Uiso 1 1 calc R U . . .
C68 C 1.04630(10) 0.5348(2) 0.88072(6) 0.0226(5) Uani 1 1 d . . . . .
H68 H 1.080074 0.525309 0.868780 0.027 Uiso 1 1 calc R U . . .
C11 C 0.35125(10) 0.9123(2) 0.42953(6) 0.0189(5) Uani 1 1 d . . . . .
H11 H 0.336847 0.992230 0.433770 0.023 Uiso 1 1 calc R U . . .
C2 C 0.27041(9) 0.9185(2) 0.50510(6) 0.0179(5) Uani 1 1 d . . . . .
C61 C 0.94590(10) 0.5953(2) 0.80496(6) 0.0221(5) Uani 1 1 d . . . . .
C60 C 0.90094(10) 0.6059(2) 0.82649(6) 0.0231(5) Uani 1 1 d . . . . .
C10 C 0.31845(10) 0.8123(2) 0.44857(6) 0.0175(5) Uani 1 1 d . . . . .
H10 H 0.284455 0.792592 0.435217 0.021 Uiso 1 1 calc R U . . .
C39 C 0.71985(10) 0.5175(2) 0.68004(6) 0.0198(5) Uani 1 1 d . . . . .
C65 C 0.94568(11) 0.5613(2) 0.91729(6) 0.0226(5) Uani 1 1 d . . . . .
H65 H 0.911999 0.569404 0.929444 0.027 Uiso 1 1 calc R U . . .
C15 C 0.41059(9) 0.8907(2) 0.44354(6) 0.0186(5) Uani 1 1 d . . . . .
H15A H 0.437984 0.940708 0.431812 0.022 Uiso 1 1 calc R U . . .
H15B H 0.413474 0.897854 0.469656 0.022 Uiso 1 1 calc R U . . .
C25 C 0.54792(10) 0.7891(2) 0.53046(6) 0.0211(5) Uani 1 1 d . . . . .
C35 C 0.69229(10) 0.5975(2) 0.62142(6) 0.0203(5) Uani 1 1 d . . . . .
H35 H 0.673519 0.654628 0.608022 0.024 Uiso 1 1 calc R U . . .
C67 C 1.04443(11) 0.5255(2) 0.91781(7) 0.0259(6) Uani 1 1 d . . . . .
H67 H 1.076829 0.510325 0.930778 0.031 Uiso 1 1 calc R U . . .
C26 C 0.59265(10) 0.7863(2) 0.55218(6) 0.0217(5) Uani 1 1 d . . . . .
C36 C 0.72088(10) 0.5079(2) 0.60425(6) 0.0227(5) Uani 1 1 d . . . . .
H36 H 0.721923 0.505286 0.579076 0.027 Uiso 1 1 calc R U . . .
C66 C 0.99402(11) 0.5386(2) 0.93604(6) 0.0247(6) Uani 1 1 d . . . . .
H66 H 0.993039 0.532033 0.961147 0.030 Uiso 1 1 calc R U . . .
C9 C 0.29764(10) 0.8107(2) 0.60096(6) 0.0230(5) Uani 1 1 d . . . . .
H9 H 0.317679 0.751223 0.612473 0.028 Uiso 1 1 calc R U . . .
C43 C 0.66557(10) 0.7034(2) 0.71048(6) 0.0226(5) Uani 1 1 d . . . . .
C42 C 0.69185(10) 0.6309(2) 0.73373(6) 0.0234(5) Uani 1 1 d . . . . .
C14 C 0.41308(10) 0.7619(2) 0.43055(6) 0.0195(5) Uani 1 1 d . . . . .
H14 H 0.447915 0.720733 0.436176 0.023 Uiso 1 1 calc R U . . .
C41 C 0.72183(10) 0.5266(2) 0.71982(6) 0.0231(5) Uani 1 1 d . . . . .
C23 C 0.44756(10) 0.8959(2) 0.64017(6) 0.0241(6) Uani 1 1 d . . . . .
H23 H 0.414881 0.914095 0.652455 0.029 Uiso 1 1 calc R U . . .
C16 C 0.36065(9) 0.7070(2) 0.44815(6) 0.0181(5) Uani 1 1 d . . . . .
H16 H 0.346429 0.641373 0.433488 0.022 Uiso 1 1 calc R U . . .
C29 C 0.56224(10) 0.7492(2) 0.49229(7) 0.0230(5) Uani 1 1 d . . . . .
H29 H 0.539592 0.681465 0.484721 0.028 Uiso 1 1 calc R U . . .
C6 C 0.23716(10) 0.9872(2) 0.56620(6) 0.0225(5) Uani 1 1 d . . . . .
H6 H 0.216578 1.046168 0.554857 0.027 Uiso 1 1 calc R U . . .
C37 C 0.74821(11) 0.4212(2) 0.62427(6) 0.0255(6) Uani 1 1 d . . . . .
H37 H 0.766587 0.359854 0.612486 0.031 Uiso 1 1 calc R U . . .
C12 C 0.35714(10) 0.8776(2) 0.38935(6) 0.0240(6) Uani 1 1 d . . . . .
H12A H 0.370053 0.944010 0.374988 0.029 Uiso 1 1 calc R U . . .
H12B H 0.321995 0.849908 0.379616 0.029 Uiso 1 1 calc R U . . .
C34 C 0.57126(10) 0.7911(2) 0.42674(6) 0.0218(5) Uani 1 1 d . . . . .
H34A H 0.563920 0.846007 0.407117 0.026 Uiso 1 1 calc R U . . .
H34B H 0.548263 0.721290 0.423625 0.026 Uiso 1 1 calc R U . . .
C32 C 0.65195(10) 0.7974(2) 0.46610(6) 0.0223(5) Uani 1 1 d . . . . .
H32 H 0.692131 0.808718 0.468950 0.027 Uiso 1 1 calc R U . . .
C27 C 0.64347(11) 0.7475(2) 0.53280(7) 0.0255(6) Uani 1 1 d . . . . .
C13 C 0.40112(11) 0.7763(2) 0.38991(6) 0.0250(6) Uani 1 1 d . . . . .
H13A H 0.386170 0.703969 0.379623 0.030 Uiso 1 1 calc R U . . .
H13B H 0.434423 0.798557 0.376741 0.030 Uiso 1 1 calc R U . . .
C30 C 0.56105(10) 0.8495(2) 0.46397(6) 0.0230(5) Uani 1 1 d . . . . .
H30 H 0.528424 0.901290 0.465184 0.028 Uiso 1 1 calc R U . . .
C7 C 0.23623(11) 0.9785(2) 0.60344(7) 0.0262(6) Uani 1 1 d . . . . .
H7 H 0.215434 1.031980 0.616997 0.031 Uiso 1 1 calc R U . . .
C38 C 0.74801(10) 0.4264(2) 0.66152(7) 0.0254(6) Uani 1 1 d . . . . .
H38 H 0.766785 0.368742 0.674699 0.031 Uiso 1 1 calc R U . . .
C8 C 0.26635(10) 0.8900(2) 0.62077(6) 0.0265(6) Uani 1 1 d . . . . .
H8 H 0.265407 0.884264 0.645894 0.032 Uiso 1 1 calc R U . . .
C47 C 0.65145(10) 0.5980(2) 0.79762(6) 0.0258(6) Uani 1 1 d . . . . .
H47 H 0.658526 0.512736 0.796237 0.031 Uiso 1 1 calc R U . . .
C49 C 0.60290(11) 0.7690(2) 0.79373(6) 0.0248(6) Uani 1 1 d . . . . .
H49 H 0.570916 0.820464 0.789014 0.030 Uiso 1 1 calc R U . . .
C46 C 0.68787(11) 0.6742(2) 0.77230(6) 0.0245(6) Uani 1 1 d . . . . .
H46 H 0.724759 0.688365 0.782736 0.029 Uiso 1 1 calc R U . . .
C33 C 0.63396(11) 0.7581(2) 0.42857(6) 0.0270(6) Uani 1 1 d . . . . .
H33A H 0.639182 0.673512 0.425551 0.032 Uiso 1 1 calc R U . . .
H33B H 0.654896 0.799268 0.409983 0.032 Uiso 1 1 calc R U . . .
C50 C 0.62287(11) 0.7674(2) 0.83310(6) 0.0273(6) Uani 1 1 d . . . . .
H50A H 0.591635 0.766228 0.849727 0.033 Uiso 1 1 calc R U . . .
H50B H 0.645810 0.835952 0.838326 0.033 Uiso 1 1 calc R U . . .
C51 C 0.65716(11) 0.6517(2) 0.83589(6) 0.0271(6) Uani 1 1 d . . . . .
H51A H 0.695762 0.668250 0.841646 0.032 Uiso 1 1 calc R U . . .
H51B H 0.641896 0.599223 0.854141 0.032 Uiso 1 1 calc R U . . .
C59 C 0.85040(11) 0.6336(2) 0.80579(7) 0.0279(6) Uani 1 1 d . . . . .
C31 C 0.61701(10) 0.9111(2) 0.47057(7) 0.0243(6) Uani 1 1 d . . . . .
H31A H 0.619902 0.944975 0.494646 0.029 Uiso 1 1 calc R U . . .
H31B H 0.625454 0.970426 0.452393 0.029 Uiso 1 1 calc R U . . .
C52 C 0.93081(10) 0.6094(2) 0.76561(6) 0.0244(6) Uani 1 1 d . . . . .
H52 H 0.940761 0.538833 0.751630 0.029 Uiso 1 1 calc R U . . .
C53 C 0.95242(11) 0.7227(2) 0.74721(7) 0.0280(6) Uani 1 1 d . . . . .
H53 H 0.991358 0.742061 0.752402 0.034 Uiso 1 1 calc R U . . .
C44 C 0.63884(11) 0.8044(2) 0.72977(7) 0.0254(6) Uani 1 1 d . . . . .
C28 C 0.62531(10) 0.7168(2) 0.49449(6) 0.0243(6) Uani 1 1 d . . . . .
H28 H 0.631709 0.633013 0.488993 0.029 Uiso 1 1 calc R U . . .
C58 C 0.86641(11) 0.6289(2) 0.76614(6) 0.0269(6) Uani 1 1 d . . . . .
H58 H 0.846971 0.564643 0.753577 0.032 Uiso 1 1 calc R U . . .
C45 C 0.65368(11) 0.7912(2) 0.76929(6) 0.0254(6) Uani 1 1 d . . . . .
H45 H 0.675348 0.859129 0.777866 0.030 Uiso 1 1 calc R U . . .
C48 C 0.59233(10) 0.6354(2) 0.78704(7) 0.0258(6) Uani 1 1 d . . . . .
H48A H 0.564132 0.602780 0.802961 0.031 Uiso 1 1 calc R U . . .
H48B H 0.583514 0.617732 0.761973 0.031 Uiso 1 1 calc R U . . .
C56 C 0.93789(11) 0.7132(3) 0.70652(7) 0.0312(6) Uani 1 1 d . . . . .
H56A H 0.948309 0.636441 0.696880 0.037 Uiso 1 1 calc R U . . .
H56B H 0.956345 0.774518 0.692615 0.037 Uiso 1 1 calc R U . . .
C57 C 0.91002(11) 0.8164(2) 0.75962(7) 0.0291(6) Uani 1 1 d . . . . .
H57A H 0.909816 0.827410 0.785685 0.035 Uiso 1 1 calc R U . . .
H57B H 0.914864 0.891785 0.747481 0.035 Uiso 1 1 calc R U . . .
C54 C 0.85912(11) 0.7479(2) 0.74596(7) 0.0297(6) Uani 1 1 d . . . . .
H54 H 0.823395 0.787334 0.750197 0.036 Uiso 1 1 calc R U . . .
C55 C 0.87388(12) 0.7298(3) 0.70600(7) 0.0359(7) Uani 1 1 d . . . . .
H55A H 0.863501 0.798329 0.691671 0.043 Uiso 1 1 calc R U . . .
H55B H 0.855469 0.660408 0.696258 0.043 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.388(3) . ?
O1 C5 1.352(3) . ?
O5 C20 1.385(3) . ?
O5 C26 1.358(3) . ?
O12 C64 1.382(3) . ?
O12 C60 1.343(3) . ?
O7 C40 1.389(3) . ?
O7 C43 1.341(3) . ?
O4 C18 1.225(3) . ?
O3 C17 1.216(3) . ?
O2 C2 1.233(3) . ?
O9 C41 1.230(3) . ?
O11 C62 1.225(3) . ?
O6 C27 1.215(3) . ?
O8 C44 1.214(3) . ?
O10 C59 1.218(3) . ?
C20 C19 1.396(3) . ?
C20 C21 1.385(3) . ?
C62 C63 1.477(3) . ?
C62 C61 1.463(3) . ?
C40 C39 1.395(3) . ?
C40 C35 1.389(3) . ?
C19 C18 1.484(3) . ?
C19 C24 1.401(3) . ?
C63 C64 1.398(3) . ?
C63 C68 1.404(3) . ?
C4 C3 1.395(3) . ?
C4 C9 1.392(3) . ?
C64 C65 1.394(3) . ?
C18 C25 1.460(3) . ?
C3 C2 1.482(3) . ?
C3 C6 1.401(3) . ?
C5 C1 1.345(3) . ?
C5 C17 1.480(3) . ?
C1 C2 1.458(3) . ?
C1 C10 1.507(3) . ?
C17 C16 1.510(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.377(3) . ?
C24 H24 0.9300 . ?
C24 C23 1.373(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.399(3) . ?
C68 H68 0.9300 . ?
C68 C67 1.374(3) . ?
C11 H11 0.9800 . ?
C11 C10 1.546(3) . ?
C11 C15 1.537(3) . ?
C11 C12 1.541(3) . ?
C61 C60 1.347(3) . ?
C61 C52 1.505(3) . ?
C60 C59 1.469(3) . ?
C10 H10 0.9800 . ?
C10 C16 1.564(3) . ?
C39 C41 1.473(3) . ?
C39 C38 1.409(3) . ?
C65 H65 0.9300 . ?
C65 C66 1.377(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.534(3) . ?
C25 C26 1.341(3) . ?
C25 C29 1.519(3) . ?
C35 H35 0.9300 . ?
C35 C36 1.378(3) . ?
C67 H67 0.9300 . ?
C67 C66 1.394(4) . ?
C26 C27 1.482(3) . ?
C36 H36 0.9300 . ?
C36 C37 1.392(4) . ?
C66 H66 0.9300 . ?
C9 H9 0.9300 . ?
C9 C8 1.380(4) . ?
C43 C42 1.344(3) . ?
C43 C44 1.491(3) . ?
C42 C41 1.475(4) . ?
C42 C46 1.508(3) . ?
C14 H14 0.9800 . ?
C14 C16 1.547(3) . ?
C14 C13 1.536(3) . ?
C23 H23 0.9300 . ?
C16 H16 0.9800 . ?
C29 H29 0.9800 . ?
C29 C30 1.542(3) . ?
C29 C28 1.562(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.378(3) . ?
C37 H37 0.9300 . ?
C37 C38 1.376(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.559(3) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 C30 1.544(3) . ?
C34 C33 1.554(3) . ?
C32 H32 0.9800 . ?
C32 C33 1.518(3) . ?
C32 C31 1.543(3) . ?
C32 C28 1.529(3) . ?
C27 C28 1.520(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C30 H30 0.9800 . ?
C30 C31 1.534(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.391(4) . ?
C38 H38 0.9300 . ?
C8 H8 0.9300 . ?
C47 H47 0.9800 . ?
C47 C46 1.543(3) . ?
C47 C51 1.544(3) . ?
C47 C48 1.533(3) . ?
C49 H49 0.9800 . ?
C49 C50 1.531(3) . ?
C49 C45 1.538(3) . ?
C49 C48 1.550(3) . ?
C46 H46 0.9800 . ?
C46 C45 1.561(4) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C50 H50A 0.9700 . ?
C50 H50B 0.9700 . ?
C50 C51 1.549(4) . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C59 C58 1.514(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C52 H52 0.9800 . ?
C52 C53 1.540(4) . ?
C52 C58 1.564(4) . ?
C53 H53 0.9800 . ?
C53 C56 1.546(3) . ?
C53 C57 1.539(4) . ?
C44 C45 1.509(3) . ?
C28 H28 0.9800 . ?
C58 H58 0.9800 . ?
C58 C54 1.548(4) . ?
C45 H45 0.9800 . ?
C48 H48A 0.9700 . ?
C48 H48B 0.9700 . ?
C56 H56A 0.9700 . ?
C56 H56B 0.9700 . ?
C56 C55 1.550(4) . ?
C57 H57A 0.9700 . ?
C57 H57B 0.9700 . ?
C57 C54 1.533(4) . ?
C54 H54 0.9800 . ?
C54 C55 1.531(4) . ?
C55 H55A 0.9700 . ?
C55 H55B 0.9700 . ?

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
C5 O1 C4 115.78(17) . . ?
C26 O5 C20 115.83(17) . . ?
C60 O12 C64 115.35(18) . . ?
C43 O7 C40 115.63(18) . . ?
O5 C20 C19 122.12(19) . . ?
O5 C20 C21 115.76(19) . . ?
C21 C20 C19 122.1(2) . . ?
O11 C62 C63 123.8(2) . . ?
O11 C62 C61 124.0(2) . . ?
C61 C62 C63 112.2(2) . . ?
O7 C40 C39 122.3(2) . . ?
O7 C40 C35 115.5(2) . . ?
C35 C40 C39 122.2(2) . . ?
C20 C19 C18 121.4(2) . . ?
C20 C19 C24 117.7(2) . . ?
C24 C19 C18 121.0(2) . . ?
C64 C63 C62 121.8(2) . . ?
C64 C63 C68 117.4(2) . . ?
C68 C63 C62 120.8(2) . . ?
O1 C4 C3 122.2(2) . . ?
O1 C4 C9 115.5(2) . . ?
C9 C4 C3 122.3(2) . . ?
O12 C64 C63 122.3(2) . . ?
O12 C64 C65 115.5(2) . . ?
C65 C64 C63 122.2(2) . . ?
O4 C18 C19 122.9(2) . . ?
O4 C18 C25 124.1(2) . . ?
C25 C18 C19 112.98(19) . . ?
C4 C3 C2 121.3(2) . . ?
C4 C3 C6 117.2(2) . . ?
C6 C3 C2 121.4(2) . . ?
O1 C5 C17 120.01(19) . . ?
C1 C5 O1 127.6(2) . . ?
C1 C5 C17 112.3(2) . . ?
C5 C1 C2 120.0(2) . . ?
C5 C1 C10 111.5(2) . . ?
C2 C1 C10 128.4(2) . . ?
O3 C17 C5 126.8(2) . . ?
O3 C17 C16 127.3(2) . . ?
C5 C17 C16 105.99(19) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 C20 118.8(2) . . ?
C22 C21 H21 120.6 . . ?
C19 C24 H24 119.5 . . ?
C23 C24 C19 120.9(2) . . ?
C23 C24 H24 119.5 . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.6(2) . . ?
C23 C22 H22 119.7 . . ?
C63 C68 H68 119.5 . . ?
C67 C68 C63 121.0(2) . . ?
C67 C68 H68 119.5 . . ?
C10 C11 H11 114.9 . . ?
C15 C11 H11 114.9 . . ?
C15 C11 C10 101.78(18) . . ?
C15 C11 C12 101.42(18) . . ?
C12 C11 H11 114.9 . . ?
C12 C11 C10 107.36(19) . . ?
O2 C2 C3 122.6(2) . . ?
O2 C2 C1 124.3(2) . . ?
C1 C2 C3 113.0(2) . . ?
C62 C61 C52 128.3(2) . . ?
C60 C61 C62 120.1(2) . . ?
C60 C61 C52 111.5(2) . . ?
O12 C60 C61 128.1(2) . . ?
O12 C60 C59 119.8(2) . . ?
C61 C60 C59 112.1(2) . . ?
C1 C10 C11 115.89(18) . . ?
C1 C10 H10 111.3 . . ?
C1 C10 C16 103.76(18) . . ?
C11 C10 H10 111.3 . . ?
C11 C10 C16 102.75(18) . . ?
C16 C10 H10 111.3 . . ?
C40 C39 C41 121.5(2) . . ?
C40 C39 C38 117.2(2) . . ?
C38 C39 C41 121.3(2) . . ?
C64 C65 H65 120.7 . . ?
C66 C65 C64 118.6(2) . . ?
C66 C65 H65 120.7 . . ?
C11 C15 H15A 112.8 . . ?
C11 C15 H15B 112.8 . . ?
H15A C15 H15B 110.2 . . ?
C14 C15 C11 94.71(18) . . ?
C14 C15 H15A 112.8 . . ?
C14 C15 H15B 112.8 . . ?
C18 C25 C29 128.5(2) . . ?
C26 C25 C18 120.0(2) . . ?
C26 C25 C29 111.4(2) . . ?
C40 C35 H35 120.5 . . ?
C36 C35 C40 119.0(2) . . ?
C36 C35 H35 120.5 . . ?
C68 C67 H67 120.0 . . ?
C68 C67 C66 120.1(2) . . ?
C66 C67 H67 120.0 . . ?
O5 C26 C27 120.1(2) . . ?
C25 C26 O5 127.6(2) . . ?
C25 C26 C27 112.3(2) . . ?
C35 C36 H36 119.7 . . ?
C35 C36 C37 120.6(2) . . ?
C37 C36 H36 119.7 . . ?
C65 C66 C67 120.7(2) . . ?
C65 C66 H66 119.6 . . ?
C67 C66 H66 119.6 . . ?
C4 C9 H9 120.6 . . ?
C8 C9 C4 118.7(2) . . ?
C8 C9 H9 120.6 . . ?
O7 C43 C42 128.0(2) . . ?
O7 C43 C44 120.6(2) . . ?
C42 C43 C44 111.4(2) . . ?
C43 C42 C41 119.6(2) . . ?
C43 C42 C46 112.0(2) . . ?
C41 C42 C46 128.3(2) . . ?
C15 C14 H14 114.7 . . ?
C15 C14 C16 102.53(18) . . ?
C15 C14 C13 101.38(19) . . ?
C16 C14 H14 114.7 . . ?
C13 C14 H14 114.7 . . ?
C13 C14 C16 107.45(19) . . ?
O9 C41 C39 123.8(2) . . ?
O9 C41 C42 123.3(2) . . ?
C39 C41 C42 112.8(2) . . ?
C24 C23 C22 119.9(2) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C17 C16 C10 106.34(18) . . ?
C17 C16 C14 114.49(19) . . ?
C17 C16 H16 110.8 . . ?
C10 C16 H16 110.8 . . ?
C14 C16 C10 103.18(18) . . ?
C14 C16 H16 110.8 . . ?
C25 C29 H29 111.8 . . ?
C25 C29 C30 114.0(2) . . ?
C25 C29 C28 103.98(19) . . ?
C30 C29 H29 111.8 . . ?
C30 C29 C28 103.04(19) . . ?
C28 C29 H29 111.8 . . ?
C3 C6 H6 119.4 . . ?
C7 C6 C3 121.2(2) . . ?
C7 C6 H6 119.4 . . ?
C36 C37 H37 120.0 . . ?
C38 C37 C36 119.9(2) . . ?
C38 C37 H37 120.0 . . ?
C11 C12 H12A 111.0 . . ?
C11 C12 H12B 111.0 . . ?
C11 C12 C13 103.69(18) . . ?
H12A C12 H12B 109.0 . . ?
C13 C12 H12A 111.0 . . ?
C13 C12 H12B 111.0 . . ?
H34A C34 H34B 109.2 . . ?
C30 C34 H34A 111.2 . . ?
C30 C34 H34B 111.2 . . ?
C30 C34 C33 102.59(18) . . ?
C33 C34 H34A 111.2 . . ?
C33 C34 H34B 111.2 . . ?
C33 C32 H32 114.6 . . ?
C33 C32 C31 100.76(19) . . ?
C33 C32 C28 109.3(2) . . ?
C31 C32 H32 114.6 . . ?
C28 C32 H32 114.6 . . ?
C28 C32 C31 101.25(18) . . ?
O6 C27 C26 125.3(2) . . ?
O6 C27 C28 128.4(2) . . ?
C26 C27 C28 106.2(2) . . ?
C14 C13 C12 102.58(18) . . ?
C14 C13 H13A 111.3 . . ?
C14 C13 H13B 111.3 . . ?
C12 C13 H13A 111.3 . . ?
C12 C13 H13B 111.3 . . ?
H13A C13 H13B 109.2 . . ?
C29 C30 C34 106.7(2) . . ?
C29 C30 H30 115.0 . . ?
C34 C30 H30 115.0 . . ?
C31 C30 C29 102.11(19) . . ?
C31 C30 C34 101.31(19) . . ?
C31 C30 H30 115.0 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.1(2) . . ?
C8 C7 H7 120.0 . . ?
C39 C38 H38 119.4 . . ?
C37 C38 C39 121.2(2) . . ?
C37 C38 H38 119.4 . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C46 C47 H47 114.8 . . ?
C46 C47 C51 106.5(2) . . ?
C51 C47 H47 114.8 . . ?
C48 C47 H47 114.8 . . ?
C48 C47 C46 102.6(2) . . ?
C48 C47 C51 102.0(2) . . ?
C50 C49 H49 114.9 . . ?
C50 C49 C45 108.0(2) . . ?
C50 C49 C48 101.1(2) . . ?
C45 C49 H49 114.9 . . ?
C45 C49 C48 101.3(2) . . ?
C48 C49 H49 114.9 . . ?
C42 C46 C47 115.2(2) . . ?
C42 C46 H46 111.5 . . ?
C42 C46 C45 103.95(19) . . ?
C47 C46 H46 111.5 . . ?
C47 C46 C45 102.5(2) . . ?
C45 C46 H46 111.5 . . ?
C34 C33 H33A 110.9 . . ?
C34 C33 H33B 110.9 . . ?
C32 C33 C34 104.21(19) . . ?
C32 C33 H33A 110.9 . . ?
C32 C33 H33B 110.9 . . ?
H33A C33 H33B 108.9 . . ?
C49 C50 H50A 111.0 . . ?
C49 C50 H50B 111.0 . . ?
C49 C50 C51 103.86(19) . . ?
H50A C50 H50B 109.0 . . ?
C51 C50 H50A 111.0 . . ?
C51 C50 H50B 111.0 . . ?
C47 C51 C50 102.93(19) . . ?
C47 C51 H51A 111.2 . . ?
C47 C51 H51B 111.2 . . ?
C50 C51 H51A 111.2 . . ?
C50 C51 H51B 111.2 . . ?
H51A C51 H51B 109.1 . . ?
O10 C59 C60 125.0(2) . . ?
O10 C59 C58 128.3(2) . . ?
C60 C59 C58 106.6(2) . . ?
C32 C31 H31A 112.8 . . ?
C32 C31 H31B 112.8 . . ?
C30 C31 C32 94.71(19) . . ?
C30 C31 H31A 112.8 . . ?
C30 C31 H31B 112.8 . . ?
H31A C31 H31B 110.2 . . ?
C61 C52 H52 111.3 . . ?
C61 C52 C53 115.7(2) . . ?
C61 C52 C58 103.97(19) . . ?
C53 C52 H52 111.3 . . ?
C53 C52 C58 102.9(2) . . ?
C58 C52 H52 111.3 . . ?
C52 C53 H53 114.9 . . ?
C52 C53 C56 107.1(2) . . ?
C56 C53 H53 114.9 . . ?
C57 C53 C52 102.5(2) . . ?
C57 C53 H53 114.9 . . ?
C57 C53 C56 100.8(2) . . ?
O8 C44 C43 125.4(2) . . ?
O8 C44 C45 128.1(2) . . ?
C43 C44 C45 106.5(2) . . ?
C29 C28 H28 111.6 . . ?
C32 C28 C29 103.35(19) . . ?
C32 C28 H28 111.6 . . ?
C27 C28 C29 105.86(19) . . ?
C27 C28 C32 112.4(2) . . ?
C27 C28 H28 111.6 . . ?
C59 C58 C52 105.58(19) . . ?
C59 C58 H58 111.2 . . ?
C59 C58 C54 114.0(2) . . ?
C52 C58 H58 111.2 . . ?
C54 C58 C52 103.2(2) . . ?
C54 C58 H58 111.2 . . ?
C49 C45 C46 103.7(2) . . ?
C49 C45 H45 111.1 . . ?
C46 C45 H45 111.1 . . ?
C44 C45 C49 113.3(2) . . ?
C44 C45 C46 106.1(2) . . ?
C44 C45 H45 111.1 . . ?
C47 C48 C49 94.35(19) . . ?
C47 C48 H48A 112.9 . . ?
C47 C48 H48B 112.9 . . ?
C49 C48 H48A 112.9 . . ?
C49 C48 H48B 112.9 . . ?
H48A C48 H48B 110.3 . . ?
C53 C56 H56A 111.1 . . ?
C53 C56 H56B 111.1 . . ?
C53 C56 C55 103.2(2) . . ?
H56A C56 H56B 109.1 . . ?
C55 C56 H56A 111.1 . . ?
C55 C56 H56B 111.1 . . ?
C53 C57 H57A 112.8 . . ?
C53 C57 H57B 112.8 . . ?
H57A C57 H57B 110.2 . . ?
C54 C57 C53 94.8(2) . . ?
C54 C57 H57A 112.8 . . ?
C54 C57 H57B 112.8 . . ?
C58 C54 H54 114.7 . . ?
C57 C54 C58 100.9(2) . . ?
C57 C54 H54 114.7 . . ?
C55 C54 C58 108.8(2) . . ?
C55 C54 C57 101.5(2) . . ?
C55 C54 H54 114.7 . . ?
C56 C55 H55A 111.0 . . ?
C56 C55 H55B 111.0 . . ?
C54 C55 C56 103.6(2) . . ?
C54 C55 H55A 111.0 . . ?
C54 C55 H55B 111.0 . . ?
H55A C55 H55B 109.0 . . ?

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 C4 C3 C2 0.2(3) . . . . ?
O1 C4 C3 C6 -179.0(2) . . . . ?
O1 C4 C9 C8 178.8(2) . . . . ?
O1 C5 C1 C2 0.1(4) . . . . ?
O1 C5 C1 C10 -178.6(2) . . . . ?
O1 C5 C17 O3 1.1(3) . . . . ?
O1 C5 C17 C16 -179.83(18) . . . . ?
O5 C20 C19 C18 0.1(3) . . . . ?
O5 C20 C19 C24 179.2(2) . . . . ?
O5 C20 C21 C22 -179.4(2) . . . . ?
O5 C26 C27 O6 -7.8(4) . . . . ?
O5 C26 C27 C28 175.4(2) . . . . ?
O12 C64 C65 C66 -178.8(2) . . . . ?
O12 C60 C59 O10 6.3(4) . . . . ?
O12 C60 C59 C58 -176.3(2) . . . . ?
O7 C40 C39 C41 -2.8(3) . . . . ?
O7 C40 C39 C38 179.7(2) . . . . ?
O7 C40 C35 C36 179.6(2) . . . . ?
O7 C43 C42 C41 -0.2(4) . . . . ?
O7 C43 C42 C46 177.3(2) . . . . ?
O7 C43 C44 O8 5.1(4) . . . . ?
O7 C43 C44 C45 -176.2(2) . . . . ?
O4 C18 C25 C26 178.6(2) . . . . ?
O4 C18 C25 C29 -3.6(4) . . . . ?
O3 C17 C16 C10 177.4(2) . . . . ?
O3 C17 C16 C14 -69.4(3) . . . . ?
O11 C62 C63 C64 -179.8(2) . . . . ?
O11 C62 C63 C68 1.0(4) . . . . ?
O11 C62 C61 C60 179.6(2) . . . . ?
O11 C62 C61 C52 1.3(4) . . . . ?
O6 C27 C28 C29 -172.5(3) . . . . ?
O6 C27 C28 C32 -60.4(3) . . . . ?
O8 C44 C45 C49 62.8(4) . . . . ?
O8 C44 C45 C46 176.0(3) . . . . ?
O10 C59 C58 C52 171.6(3) . . . . ?
O10 C59 C58 C54 59.1(4) . . . . ?
C20 O5 C26 C25 2.3(3) . . . . ?
C20 O5 C26 C27 -176.3(2) . . . . ?
C20 C19 C18 O4 -178.9(2) . . . . ?
C20 C19 C18 C25 2.7(3) . . . . ?
C20 C19 C24 C23 0.1(3) . . . . ?
C20 C21 C22 C23 0.3(4) . . . . ?
C62 C63 C64 O12 -0.2(3) . . . . ?
C62 C63 C64 C65 180.0(2) . . . . ?
C62 C63 C68 C67 179.2(2) . . . . ?
C62 C61 C60 O12 0.7(4) . . . . ?
C62 C61 C60 C59 178.9(2) . . . . ?
C62 C61 C52 C53 -70.8(3) . . . . ?
C62 C61 C52 C58 177.2(2) . . . . ?
C40 O7 C43 C42 -2.6(4) . . . . ?
C40 O7 C43 C44 176.0(2) . . . . ?
C40 C39 C41 O9 -177.8(2) . . . . ?
C40 C39 C41 C42 -0.1(3) . . . . ?
C40 C39 C38 C37 0.5(4) . . . . ?
C40 C35 C36 C37 1.1(3) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C19 C18 C25 C26 -3.0(3) . . . . ?
C19 C18 C25 C29 174.9(2) . . . . ?
C19 C24 C23 C22 0.4(4) . . . . ?
C63 C62 C61 C60 0.2(3) . . . . ?
C63 C62 C61 C52 -178.0(2) . . . . ?
C63 C64 C65 C66 1.1(3) . . . . ?
C63 C68 C67 C66 0.5(4) . . . . ?
C4 O1 C5 C1 -0.8(3) . . . . ?
C4 O1 C5 C17 179.42(19) . . . . ?
C4 C3 C2 O2 -179.8(2) . . . . ?
C4 C3 C2 C1 -0.9(3) . . . . ?
C4 C3 C6 C7 0.2(3) . . . . ?
C4 C9 C8 C7 0.3(4) . . . . ?
C64 O12 C60 C61 -1.3(4) . . . . ?
C64 O12 C60 C59 -179.4(2) . . . . ?
C64 C63 C68 C67 0.0(3) . . . . ?
C64 C65 C66 C67 -0.6(4) . . . . ?
C18 C19 C24 C23 179.3(2) . . . . ?
C18 C25 C26 O5 0.6(4) . . . . ?
C18 C25 C26 C27 179.3(2) . . . . ?
C18 C25 C29 C30 72.2(3) . . . . ?
C18 C25 C29 C28 -176.4(2) . . . . ?
C3 C4 C9 C8 -0.8(4) . . . . ?
C3 C6 C7 C8 -0.6(4) . . . . ?
C5 O1 C4 C3 0.6(3) . . . . ?
C5 O1 C4 C9 -179.01(19) . . . . ?
C5 C1 C2 O2 179.6(2) . . . . ?
C5 C1 C2 C3 0.7(3) . . . . ?
C5 C1 C10 C11 -113.9(2) . . . . ?
C5 C1 C10 C16 -2.1(2) . . . . ?
C5 C17 C16 C10 -1.7(2) . . . . ?
C5 C17 C16 C14 111.6(2) . . . . ?
C1 C5 C17 O3 -178.7(2) . . . . ?
C1 C5 C17 C16 0.4(3) . . . . ?
C1 C10 C16 C17 2.3(2) . . . . ?
C1 C10 C16 C14 -118.57(18) . . . . ?
C17 C5 C1 C2 179.91(19) . . . . ?
C17 C5 C1 C10 1.2(3) . . . . ?
C21 C20 C19 C18 -179.6(2) . . . . ?
C21 C20 C19 C24 -0.4(3) . . . . ?
C21 C22 C23 C24 -0.6(4) . . . . ?
C24 C19 C18 O4 2.0(3) . . . . ?
C24 C19 C18 C25 -176.5(2) . . . . ?
C68 C63 C64 O12 179.0(2) . . . . ?
C68 C63 C64 C65 -0.8(3) . . . . ?
C68 C67 C66 C65 -0.1(4) . . . . ?
C11 C10 C16 C17 123.33(19) . . . . ?
C11 C10 C16 C14 2.5(2) . . . . ?
C11 C15 C14 C16 -54.2(2) . . . . ?
C11 C15 C14 C13 56.8(2) . . . . ?
C11 C12 C13 C14 2.4(2) . . . . ?
C2 C3 C6 C7 -179.1(2) . . . . ?
C2 C1 C10 C11 67.5(3) . . . . ?
C2 C1 C10 C16 179.3(2) . . . . ?
C61 C62 C63 C64 -0.4(3) . . . . ?
C61 C62 C63 C68 -179.6(2) . . . . ?
C61 C60 C59 O10 -172.0(3) . . . . ?
C61 C60 C59 C58 5.3(3) . . . . ?
C61 C52 C53 C56 174.1(2) . . . . ?
C61 C52 C53 C57 -80.3(2) . . . . ?
C61 C52 C58 C59 4.2(3) . . . . ?
C61 C52 C58 C54 124.1(2) . . . . ?
C60 O12 C64 C63 1.0(3) . . . . ?
C60 O12 C64 C65 -179.2(2) . . . . ?
C60 C61 C52 C53 110.8(3) . . . . ?
C60 C61 C52 C58 -1.1(3) . . . . ?
C60 C59 C58 C52 -5.7(3) . . . . ?
C60 C59 C58 C54 -118.2(2) . . . . ?
C10 C1 C2 O2 -1.9(4) . . . . ?
C10 C1 C2 C3 179.2(2) . . . . ?
C10 C11 C15 C14 55.82(19) . . . . ?
C10 C11 C12 C13 -73.2(2) . . . . ?
C39 C40 C35 C36 0.4(3) . . . . ?
C15 C11 C10 C1 75.6(2) . . . . ?
C15 C11 C10 C16 -36.8(2) . . . . ?
C15 C11 C12 C13 33.1(2) . . . . ?
C15 C14 C16 C17 -82.4(2) . . . . ?
C15 C14 C16 C10 32.7(2) . . . . ?
C15 C14 C13 C12 -37.2(2) . . . . ?
C25 C26 C27 O6 173.4(3) . . . . ?
C25 C26 C27 C28 -3.4(3) . . . . ?
C25 C29 C30 C34 -175.0(2) . . . . ?
C25 C29 C30 C31 79.1(2) . . . . ?
C25 C29 C28 C32 -121.8(2) . . . . ?
C25 C29 C28 C27 -3.5(2) . . . . ?
C35 C40 C39 C41 176.4(2) . . . . ?
C35 C40 C39 C38 -1.2(3) . . . . ?
C35 C36 C37 C38 -1.7(4) . . . . ?
C26 O5 C20 C19 -2.6(3) . . . . ?
C26 O5 C20 C21 177.1(2) . . . . ?
C26 C25 C29 C30 -109.9(2) . . . . ?
C26 C25 C29 C28 1.6(3) . . . . ?
C26 C27 C28 C29 4.2(3) . . . . ?
C26 C27 C28 C32 116.3(2) . . . . ?
C36 C37 C38 C39 0.9(4) . . . . ?
C9 C4 C3 C2 179.8(2) . . . . ?
C9 C4 C3 C6 0.6(3) . . . . ?
C43 O7 C40 C39 4.0(3) . . . . ?
C43 O7 C40 C35 -175.2(2) . . . . ?
C43 C42 C41 O9 179.2(2) . . . . ?
C43 C42 C41 C39 1.5(3) . . . . ?
C43 C42 C46 C47 111.0(3) . . . . ?
C43 C42 C46 C45 -0.4(3) . . . . ?
C43 C44 C45 C49 -115.9(2) . . . . ?
C43 C44 C45 C46 -2.7(3) . . . . ?
C42 C43 C44 O8 -176.1(3) . . . . ?
C42 C43 C44 C45 2.6(3) . . . . ?
C42 C46 C45 C49 121.6(2) . . . . ?
C42 C46 C45 C44 1.9(3) . . . . ?
C41 C39 C38 C37 -177.0(2) . . . . ?
C41 C42 C46 C47 -71.8(3) . . . . ?
C41 C42 C46 C45 176.9(2) . . . . ?
C16 C14 C13 C12 70.0(2) . . . . ?
C29 C25 C26 O5 -177.6(2) . . . . ?
C29 C25 C26 C27 1.1(3) . . . . ?
C29 C30 C31 C32 54.5(2) . . . . ?
C6 C3 C2 O2 -0.5(3) . . . . ?
C6 C3 C2 C1 178.3(2) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?
C12 C11 C10 C1 -178.30(19) . . . . ?
C12 C11 C10 C16 69.3(2) . . . . ?
C12 C11 C15 C14 -54.9(2) . . . . ?
C34 C30 C31 C32 -55.5(2) . . . . ?
C13 C14 C16 C17 171.21(19) . . . . ?
C13 C14 C16 C10 -73.7(2) . . . . ?
C30 C29 C28 C32 -2.6(2) . . . . ?
C30 C29 C28 C27 115.7(2) . . . . ?
C30 C34 C33 C32 1.3(2) . . . . ?
C38 C39 C41 O9 -0.3(4) . . . . ?
C38 C39 C41 C42 177.4(2) . . . . ?
C47 C46 C45 C49 1.2(2) . . . . ?
C47 C46 C45 C44 -118.4(2) . . . . ?
C49 C50 C51 C47 -1.5(3) . . . . ?
C46 C42 C41 O9 2.2(4) . . . . ?
C46 C42 C41 C39 -175.5(2) . . . . ?
C46 C47 C51 C50 73.0(2) . . . . ?
C46 C47 C48 C49 -55.1(2) . . . . ?
C33 C34 C30 C29 -72.2(2) . . . . ?
C33 C34 C30 C31 34.3(2) . . . . ?
C33 C32 C31 C30 56.3(2) . . . . ?
C33 C32 C28 C29 -68.8(2) . . . . ?
C33 C32 C28 C27 177.5(2) . . . . ?
C50 C49 C45 C46 70.0(2) . . . . ?
C50 C49 C45 C44 -175.4(2) . . . . ?
C50 C49 C48 C47 -55.8(2) . . . . ?
C51 C47 C46 C42 175.4(2) . . . . ?
C51 C47 C46 C45 -72.4(2) . . . . ?
C51 C47 C48 C49 55.0(2) . . . . ?
C59 C58 C54 C57 76.5(3) . . . . ?
C59 C58 C54 C55 -177.3(2) . . . . ?
C31 C32 C33 C34 -36.2(2) . . . . ?
C31 C32 C28 C29 36.9(2) . . . . ?
C31 C32 C28 C27 -76.7(2) . . . . ?
C52 C61 C60 O12 179.2(2) . . . . ?
C52 C61 C60 C59 -2.6(3) . . . . ?
C52 C53 C56 C55 71.5(3) . . . . ?
C52 C53 C57 C54 -54.7(2) . . . . ?
C52 C58 C54 C57 -37.5(2) . . . . ?
C52 C58 C54 C55 68.8(2) . . . . ?
C53 C52 C58 C59 -116.8(2) . . . . ?
C53 C52 C58 C54 3.1(2) . . . . ?
C53 C56 C55 C54 0.4(3) . . . . ?
C53 C57 C54 C58 56.1(2) . . . . ?
C53 C57 C54 C55 -55.8(2) . . . . ?
C44 C43 C42 C41 -178.9(2) . . . . ?
C44 C43 C42 C46 -1.4(3) . . . . ?
C28 C29 C30 C34 73.0(2) . . . . ?
C28 C29 C30 C31 -32.9(2) . . . . ?
C28 C32 C33 C34 69.9(2) . . . . ?
C28 C32 C31 C30 -56.1(2) . . . . ?
C58 C52 C53 C56 -73.3(2) . . . . ?
C58 C52 C53 C57 32.3(2) . . . . ?
C58 C54 C55 C56 -71.0(3) . . . . ?
C45 C49 C50 C51 -69.8(2) . . . . ?
C45 C49 C48 C47 55.4(2) . . . . ?
C48 C47 C46 C42 -77.9(2) . . . . ?
C48 C47 C46 C45 34.3(2) . . . . ?
C48 C47 C51 C50 -34.1(2) . . . . ?
C48 C49 C50 C51 36.1(2) . . . . ?
C48 C49 C45 C46 -35.7(2) . . . . ?
C48 C49 C45 C44 78.9(2) . . . . ?
C56 C53 C57 C54 55.7(2) . . . . ?
C57 C53 C56 C55 -35.4(3) . . . . ?
C57 C54 C55 C56 34.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.381
_oxdiff_exptl_absorpt_empirical_full_min 0.761
####################################################################### 
# 
# 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_86-21_tw
_database_code_depnum_ccdc_archive 'CCDC 2056366'
loop_
_audit_author_name
_audit_author_address
'Han Wen-Yong'
;Zunyi Medical University
China
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;
_audit_creation_date             2020-08-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 O3'
_chemical_formula_sum            'C17 H12 O3'
_chemical_formula_weight         264.27
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.5036(10)
_cell_length_b                   8.1424(13)
_cell_length_c                   13.547(2)
_cell_angle_alpha                84.568(13)
_cell_angle_beta                 85.441(14)
_cell_angle_gamma                89.725(14)
_cell_volume                     602.42(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1312
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.7010
_cell_measurement_theta_min      2.8270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_av_unetI/netI     0.1121
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            2104
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.005
_diffrn_reflns_theta_max         25.005
_diffrn_reflns_theta_min         2.513
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -55.00  36.00   1.00    7.00    --   11.90 -57.00-180.00   91
  2  ω    -12.00  80.00   1.00    7.00    --   11.90  77.00  90.00   92
  3  ω    -15.00  85.00   1.00    7.00    --   11.90  57.00 -30.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0388657000
_diffrn_orient_matrix_UB_12      -0.0666624000
_diffrn_orient_matrix_UB_13      -0.0250550000
_diffrn_orient_matrix_UB_21      0.0157931000
_diffrn_orient_matrix_UB_22      -0.0549686000
_diffrn_orient_matrix_UB_23      0.0428299000
_diffrn_orient_matrix_UB_31      -0.1222739000
_diffrn_orient_matrix_UB_32      0.0138311000
_diffrn_orient_matrix_UB_33      0.0179248000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1415
_reflns_number_total             2104
_reflns_odcompleteness_completeness 98.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1452
_refine_ls_R_factor_gt           0.1031
_refine_ls_restrained_S_all      1.101
_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)+(0.0784P)²+3.2921P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2622
_refine_ls_wR_factor_ref         0.2866
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.781(3)
 0.219(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C16(H16)
3.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 -0.7772(4) -0.3835(3) -0.41434(17) 0.0202(6) Uani 1 1 d . . . . .
O2 O -0.1690(4) -0.1283(3) -0.34999(19) 0.0249(7) Uani 1 1 d . . . . .
O3 O -1.0461(5) -0.5318(3) -0.23759(19) 0.0243(7) Uani 1 1 d . . . . .
C1 C -0.6214(6) -0.3079(4) -0.4928(3) 0.0214(9) Uani 1 1 d . . . . .
C2 C -0.6812(7) -0.3265(4) -0.5866(3) 0.0226(9) Uani 1 1 d . . . . .
H2 H -0.821095 -0.384056 -0.596872 0.027 Uiso 1 1 calc R U . . .
C3 C -0.5300(7) -0.2582(4) -0.6669(3) 0.0231(10) Uani 1 1 d . . . . .
H3 H -0.567574 -0.268949 -0.731722 0.028 Uiso 1 1 calc R U . . .
C4 C -0.3194(7) -0.1726(5) -0.6487(3) 0.0246(10) Uani 1 1 d . . . . .
H4 H -0.216034 -0.128250 -0.702133 0.029 Uiso 1 1 calc R U . . .
C5 C -0.2641(7) -0.1535(4) -0.5543(3) 0.0217(9) Uani 1 1 d . . . . .
H5 H -0.126023 -0.093835 -0.544245 0.026 Uiso 1 1 calc R U . . .
C6 C -0.4116(6) -0.2220(4) -0.4727(3) 0.0199(9) Uani 1 1 d . . . . .
C7 C -0.3505(6) -0.2021(4) -0.3685(3) 0.0204(9) Uani 1 1 d . . . . .
C8 C -0.5230(6) -0.2854(5) -0.2953(3) 0.0211(9) Uani 1 1 d . . . . .
C9 C -0.7159(7) -0.3678(5) -0.3229(3) 0.0221(9) Uani 1 1 d . . . . .
C10 C -0.8610(6) -0.4501(4) -0.2358(3) 0.0196(9) Uani 1 1 d . . . . .
C11 C -0.7326(6) -0.4139(5) -0.1440(3) 0.0222(9) Uani 1 1 d . . . . .
H11 H -0.677648 -0.515839 -0.108135 0.027 Uiso 1 1 calc R U . . .
C12 C -0.5140(7) -0.3006(5) -0.1844(3) 0.0225(9) Uani 1 1 d . . . . .
H12 H -0.359392 -0.348542 -0.164712 0.027 Uiso 1 1 calc R U . . .
C13 C -0.5749(7) -0.1383(4) -0.1326(3) 0.0210(9) Uani 1 1 d . . . . .
H13 H -0.489130 -0.037980 -0.161826 0.025 Uiso 1 1 calc R U . . .
C14 C -0.5451(7) -0.1885(4) -0.0226(3) 0.0214(9) Uani 1 1 d . . . . .
H14 H -0.419247 -0.155630 0.013137 0.026 Uiso 1 1 calc R U . . .
C15 C -0.7281(7) -0.2862(5) 0.0132(3) 0.0232(10) Uani 1 1 d . . . . .
H15 H -0.755615 -0.334078 0.078170 0.028 Uiso 1 1 calc R U . . .
C16 C -0.8859(6) -0.3056(5) -0.0725(3) 0.0205(9) Uani 1 1 d . . . . .
H16 H -1.054426 -0.341401 -0.053863 0.025 Uiso 1 1 calc R U . . .
C17 C -0.8532(6) -0.1352(5) -0.1310(3) 0.0228(9) Uani 1 1 d . . . . .
H17A H -0.911241 -0.131269 -0.196957 0.027 Uiso 1 1 calc R U . . .
H17B H -0.925685 -0.047084 -0.095248 0.027 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 C1 1.407(4) . ?
O1 C9 1.327(4) . ?
O2 C7 1.223(4) . ?
O3 C10 1.222(4) . ?
C1 C2 1.359(5) . ?
C1 C6 1.411(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.405(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.361(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(5) . ?
C6 C7 1.501(5) . ?
C7 C8 1.440(5) . ?
C8 C9 1.354(5) . ?
C8 C12 1.501(5) . ?
C9 C10 1.479(5) . ?
C10 C11 1.531(5) . ?
C11 H11 0.9800 . ?
C11 C12 1.552(5) . ?
C11 C16 1.566(5) . ?
C12 H12 0.9800 . ?
C12 C13 1.576(5) . ?
C13 H13 0.9800 . ?
C13 C14 1.529(5) . ?
C13 C17 1.530(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.319(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.524(5) . ?
C16 H16 0.9800 . ?
C16 C17 1.536(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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
C9 O1 C1 116.5(3) . . ?
O1 C1 C6 120.3(3) . . ?
C2 C1 O1 116.6(3) . . ?
C2 C1 C6 123.0(3) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.0(4) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.0(4) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C7 122.0(3) . . ?
C5 C6 C1 116.9(3) . . ?
C5 C6 C7 121.1(3) . . ?
O2 C7 C6 122.7(3) . . ?
O2 C7 C8 125.2(4) . . ?
C8 C7 C6 112.1(3) . . ?
C7 C8 C12 127.3(3) . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 C12 111.7(3) . . ?
O1 C9 C8 128.0(3) . . ?
O1 C9 C10 120.4(3) . . ?
C8 C9 C10 111.5(3) . . ?
O3 C10 C9 126.3(3) . . ?
O3 C10 C11 127.2(3) . . ?
C9 C10 C11 106.5(3) . . ?
C10 C11 H11 111.3 . . ?
C10 C11 C12 105.3(3) . . ?
C10 C11 C16 113.9(3) . . ?
C12 C11 H11 111.3 . . ?
C12 C11 C16 103.3(3) . . ?
C16 C11 H11 111.3 . . ?
C8 C12 C11 104.9(3) . . ?
C8 C12 H12 111.3 . . ?
C8 C12 C13 115.5(3) . . ?
C11 C12 H12 111.3 . . ?
C11 C12 C13 102.1(3) . . ?
C13 C12 H12 111.3 . . ?
C12 C13 H13 116.4 . . ?
C14 C13 C12 104.0(3) . . ?
C14 C13 H13 116.4 . . ?
C14 C13 C17 100.0(3) . . ?
C17 C13 C12 101.3(3) . . ?
C17 C13 H13 116.4 . . ?
C13 C14 H14 125.8 . . ?
C15 C14 C13 108.5(3) . . ?
C15 C14 H14 125.8 . . ?
C14 C15 H15 126.6 . . ?
C14 C15 C16 106.9(3) . . ?
C16 C15 H15 126.6 . . ?
C11 C16 H16 116.1 . . ?
C15 C16 C11 105.4(3) . . ?
C15 C16 H16 116.1 . . ?
C15 C16 C17 100.7(3) . . ?
C17 C16 C11 100.3(3) . . ?
C17 C16 H16 116.1 . . ?
C13 C17 C16 94.1(3) . . ?
C13 C17 H17A 112.9 . . ?
C13 C17 H17B 112.9 . . ?
C16 C17 H17A 112.9 . . ?
C16 C17 H17B 112.9 . . ?
H17A C17 H17B 110.3 . . ?

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 C3 -178.3(3) . . . . ?
O1 C1 C6 C5 178.7(3) . . . . ?
O1 C1 C6 C7 -2.3(5) . . . . ?
O1 C9 C10 O3 -2.5(6) . . . . ?
O1 C9 C10 C11 177.0(3) . . . . ?
O2 C7 C8 C9 -178.3(4) . . . . ?
O2 C7 C8 C12 -1.0(6) . . . . ?
O3 C10 C11 C12 -178.1(4) . . . . ?
O3 C10 C11 C16 -65.6(5) . . . . ?
C1 O1 C9 C8 1.1(5) . . . . ?
C1 O1 C9 C10 -176.8(3) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C1 C6 C7 O2 179.8(3) . . . . ?
C1 C6 C7 C8 2.4(5) . . . . ?
C2 C1 C6 C5 0.6(5) . . . . ?
C2 C1 C6 C7 179.6(3) . . . . ?
C2 C3 C4 C5 -1.1(6) . . . . ?
C3 C4 C5 C6 1.7(6) . . . . ?
C4 C5 C6 C1 -1.4(5) . . . . ?
C4 C5 C6 C7 179.6(3) . . . . ?
C5 C6 C7 O2 -1.2(5) . . . . ?
C5 C6 C7 C8 -178.7(3) . . . . ?
C6 C1 C2 C3 0.0(6) . . . . ?
C6 C7 C8 C9 -0.9(5) . . . . ?
C6 C7 C8 C12 176.4(3) . . . . ?
C7 C8 C9 O1 -0.9(6) . . . . ?
C7 C8 C9 C10 177.2(3) . . . . ?
C7 C8 C12 C11 -175.6(3) . . . . ?
C7 C8 C12 C13 72.9(5) . . . . ?
C8 C9 C10 O3 179.2(4) . . . . ?
C8 C9 C10 C11 -1.3(4) . . . . ?
C8 C12 C13 C14 -178.5(3) . . . . ?
C8 C12 C13 C17 78.1(3) . . . . ?
C9 O1 C1 C2 178.8(3) . . . . ?
C9 O1 C1 C6 0.5(5) . . . . ?
C9 C8 C12 C11 2.0(4) . . . . ?
C9 C8 C12 C13 -109.6(4) . . . . ?
C9 C10 C11 C12 2.4(4) . . . . ?
C9 C10 C11 C16 114.9(3) . . . . ?
C10 C11 C12 C8 -2.6(4) . . . . ?
C10 C11 C12 C13 118.2(3) . . . . ?
C10 C11 C16 C15 179.4(3) . . . . ?
C10 C11 C16 C17 -76.3(3) . . . . ?
C11 C12 C13 C14 68.4(3) . . . . ?
C11 C12 C13 C17 -35.0(3) . . . . ?
C11 C16 C17 C13 -58.1(3) . . . . ?
C12 C8 C9 O1 -178.6(3) . . . . ?
C12 C8 C9 C10 -0.5(4) . . . . ?
C12 C11 C16 C15 -66.8(3) . . . . ?
C12 C11 C16 C17 37.4(3) . . . . ?
C12 C13 C14 C15 -71.7(4) . . . . ?
C12 C13 C17 C16 57.4(3) . . . . ?
C13 C14 C15 C16 0.4(4) . . . . ?
C14 C13 C17 C16 -49.1(3) . . . . ?
C14 C15 C16 C11 70.6(4) . . . . ?
C14 C15 C16 C17 -33.3(4) . . . . ?
C15 C16 C17 C13 50.0(3) . . . . ?
C16 C11 C12 C8 -122.4(3) . . . . ?
C16 C11 C12 C13 -1.6(3) . . . . ?
C17 C13 C14 C15 32.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.819
_oxdiff_exptl_absorpt_empirical_full_min 0.583
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.781(3)
2 0.219(3)

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

data_exp_2336
_database_code_depnum_ccdc_archive 'CCDC 2056382'
loop_
_audit_author_name
_audit_author_address
'Han Wen-Yong'
;Zunyi Medical University
China
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;
_audit_creation_date             2020-09-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H22 O3'
_chemical_formula_sum            'C31 H22 O3'
_chemical_formula_weight         442.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   14.2504(6)
_cell_length_b                   6.3375(3)
_cell_length_c                   23.4812(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.254(4)
_cell_angle_gamma                90
_cell_volume                     2093.04(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3529
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.1570
_cell_measurement_theta_min      3.3740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            4126
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.909
_diffrn_reflns_theta_min         3.403
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  29.00   1.00    1.02    --  -40.73  38.00-150.00   89
  2  ω     54.00  87.00   1.00    1.02    --   40.73-125.00-120.00   33
  3  ω     54.00 133.00   1.00    2.00    --  107.58 -45.00   0.00   79
  4  ω     69.00 122.00   1.00    2.00    --  107.58-125.00  30.00   53
  5  ω     69.00 108.00   1.00    2.00    --  107.58 -94.00 150.00   39
  6  ω     70.00 135.00   1.00    2.00    --  107.58 -30.00 120.00   65
  7  ω     84.00 164.00   1.00    2.00    --  107.58  45.00 -60.00   80
  8  ω    121.00 178.00   1.00    2.00    --  107.58  45.00-180.00   57
  9  ω     35.00  65.00   1.00    2.00    --  107.58-125.00  30.00   30
 10  ω     31.00  58.00   1.00    2.00    --  107.58 -30.00 120.00   27
 11  ω   -116.00 -14.00   1.00    1.02    --  -40.73 -77.00  60.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0674580000
_diffrn_orient_matrix_UB_12      -0.0232928000
_diffrn_orient_matrix_UB_13      -0.0447818000
_diffrn_orient_matrix_UB_21      0.0829788000
_diffrn_orient_matrix_UB_22      0.0846778000
_diffrn_orient_matrix_UB_23      0.0443916000
_diffrn_orient_matrix_UB_31      0.0239403000
_diffrn_orient_matrix_UB_32      -0.2265181000
_diffrn_orient_matrix_UB_33      0.0210317000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3481
_reflns_number_total             4126
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.132
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1377
_refine_ls_R_factor_gt           0.1271
_refine_ls_restrained_S_all      1.044
_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)+(0.0612P)²+25.8924P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3248
_refine_ls_wR_factor_ref         0.3292
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.756(8)
 0.244(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C25(H25)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C21(H21), C22(H22), C23(H23), C24(H24),
 C28(H28), C29(H29), C30(H30), C31(H31)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.2942(4) 0.6916(9) 0.3529(2) 0.0330(12) Uani 1 1 d . . . . .
O2 O 0.4233(3) 0.1573(8) 0.43176(19) 0.0271(11) Uani 1 1 d . . . . .
O3 O 0.4941(4) -0.1102(8) 0.3485(2) 0.0297(11) Uani 1 1 d . . . . .
C1 C 0.3519(4) 0.5070(12) 0.4401(3) 0.0254(14) Uani 1 1 d . . . . .
C2 C 0.3280(5) 0.6613(12) 0.4774(3) 0.0291(15) Uani 1 1 d . . . . .
H2 H 0.298897 0.785286 0.462477 0.035 Uiso 1 1 calc R U . . .
C3 C 0.3472(5) 0.6314(14) 0.5365(3) 0.0356(18) Uani 1 1 d . . . . .
H3 H 0.331210 0.736228 0.560934 0.043 Uiso 1 1 calc R U . . .
C4 C 0.3896(5) 0.4487(13) 0.5597(3) 0.0315(17) Uani 1 1 d . . . . .
H4 H 0.401375 0.431028 0.599481 0.038 Uiso 1 1 calc R U . . .
C5 C 0.4150(5) 0.2895(13) 0.5239(3) 0.0285(15) Uani 1 1 d . . . . .
H5 H 0.443734 0.165908 0.539332 0.034 Uiso 1 1 calc R U . . .
C6 C 0.3962(5) 0.3207(11) 0.4649(3) 0.0257(14) Uani 1 1 d . . . . .
C7 C 0.4069(5) 0.1897(11) 0.3744(3) 0.0226(13) Uani 1 1 d . . . . .
C8 C 0.3644(4) 0.3578(11) 0.3458(3) 0.0240(14) Uani 1 1 d . . . . .
C9 C 0.3328(4) 0.5345(12) 0.3772(3) 0.0258(15) Uani 1 1 d . . . . .
C10 C 0.3626(5) 0.3369(11) 0.2822(3) 0.0230(14) Uani 1 1 d . . . . .
H10 H 0.297782 0.349115 0.260884 0.028 Uiso 1 1 calc R U . . .
C11 C 0.4056(5) 0.1161(11) 0.2739(3) 0.0240(14) Uani 1 1 d . . . . .
H11 H 0.358900 0.019607 0.252586 0.029 Uiso 1 1 calc R U . . .
C12 C 0.4424(5) 0.0374(11) 0.3347(3) 0.0250(14) Uani 1 1 d . . . . .
C13 C 0.4878(4) 0.1655(11) 0.2404(3) 0.0216(13) Uani 1 1 d . . . . .
H13 H 0.534408 0.051648 0.240581 0.026 Uiso 1 1 calc R U . . .
C14 C 0.5268(4) 0.3668(10) 0.2720(3) 0.0213(13) Uani 1 1 d . . . . .
H14A H 0.578150 0.430299 0.255408 0.026 Uiso 1 1 calc R U . . .
H14B H 0.546047 0.345628 0.313148 0.026 Uiso 1 1 calc R U . . .
C15 C 0.4325(4) 0.4888(10) 0.2573(3) 0.0203(13) Uani 1 1 d . . . . .
H15 H 0.434009 0.633516 0.272144 0.024 Uiso 1 1 calc R U . . .
C16 C 0.4093(4) 0.4693(11) 0.1914(3) 0.0220(14) Uani 1 1 d . . . . .
H16 H 0.340350 0.480978 0.179404 0.026 Uiso 1 1 calc R U . . .
C17 C 0.4414(4) 0.2413(11) 0.1793(3) 0.0205(13) Uani 1 1 d . . . . .
H17 H 0.384570 0.155763 0.166719 0.025 Uiso 1 1 calc R U . . .
C18 C 0.5030(4) 0.2431(11) 0.1301(3) 0.0206(13) Uani 1 1 d . . . . .
H18 H 0.520228 0.100576 0.119254 0.025 Uiso 1 1 calc R U . . .
C19 C 0.4445(4) 0.3612(12) 0.0798(3) 0.0238(14) Uani 1 1 d . . . . .
C20 C 0.4220(4) 0.5655(11) 0.0933(3) 0.0232(14) Uani 1 1 d . . . . .
C21 C 0.3686(5) 0.6933(13) 0.0526(3) 0.0300(16) Uani 1 1 d . . . . .
H21 H 0.351581 0.828628 0.062340 0.036 Uiso 1 1 calc R U . . .
C22 C 0.3408(5) 0.6168(13) -0.0031(3) 0.0326(17) Uani 1 1 d . . . . .
H22 H 0.305885 0.701911 -0.031096 0.039 Uiso 1 1 calc R U . . .
C23 C 0.3651(5) 0.4142(13) -0.0168(3) 0.0321(17) Uani 1 1 d . . . . .
H23 H 0.346358 0.364253 -0.054103 0.038 Uiso 1 1 calc R U . . .
C24 C 0.4171(5) 0.2835(12) 0.0242(3) 0.0265(15) Uani 1 1 d . . . . .
H24 H 0.433266 0.147293 0.014679 0.032 Uiso 1 1 calc R U . . .
C25 C 0.4606(5) 0.6265(11) 0.1551(3) 0.0234(14) Uani 1 1 d . . . . .
H25 H 0.446838 0.774056 0.163163 0.028 Uiso 1 1 calc R U . . .
C26 C 0.5667(5) 0.5827(11) 0.1633(3) 0.0225(14) Uani 1 1 d . . . . .
C27 C 0.5887(5) 0.3780(11) 0.1498(2) 0.0208(13) Uani 1 1 d . . . . .
C28 C 0.6826(5) 0.3125(12) 0.1543(3) 0.0255(14) Uani 1 1 d . . . . .
H28 H 0.696743 0.174114 0.145507 0.031 Uiso 1 1 calc R U . . .
C29 C 0.7565(5) 0.4583(13) 0.1723(3) 0.0312(16) Uani 1 1 d . . . . .
H29 H 0.819752 0.417601 0.175003 0.037 Uiso 1 1 calc R U . . .
C30 C 0.7335(5) 0.6628(13) 0.1857(3) 0.0332(17) Uani 1 1 d . . . . .
H30 H 0.781776 0.759286 0.197776 0.040 Uiso 1 1 calc R U . . .
C31 C 0.6390(5) 0.7259(12) 0.1815(3) 0.0276(15) Uani 1 1 d . . . . .
H31 H 0.624348 0.863288 0.190862 0.033 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 C9 1.232(8) . ?
O2 C6 1.387(8) . ?
O2 C7 1.344(7) . ?
O3 C12 1.203(8) . ?
C1 C2 1.391(10) . ?
C1 C6 1.419(10) . ?
C1 C9 1.468(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.397(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(9) . ?
C7 C8 1.350(9) . ?
C7 C12 1.487(9) . ?
C8 C9 1.451(10) . ?
C8 C10 1.496(9) . ?
C10 H10 0.9800 . ?
C10 C11 1.553(9) . ?
C10 C15 1.564(9) . ?
C11 H11 0.9800 . ?
C11 C12 1.524(9) . ?
C11 C13 1.543(9) . ?
C13 H13 0.9800 . ?
C13 C14 1.534(9) . ?
C13 C17 1.556(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.540(9) . ?
C15 H15 0.9800 . ?
C15 C16 1.535(8) . ?
C16 H16 0.9800 . ?
C16 C17 1.555(9) . ?
C16 C25 1.568(9) . ?
C17 H17 0.9800 . ?
C17 C18 1.561(8) . ?
C18 H18 0.9800 . ?
C18 C19 1.527(9) . ?
C18 C27 1.502(9) . ?
C19 C20 1.383(10) . ?
C19 C24 1.391(9) . ?
C20 C21 1.384(9) . ?
C20 C25 1.515(9) . ?
C21 H21 0.9300 . ?
C21 C22 1.392(10) . ?
C22 H22 0.9300 . ?
C22 C23 1.381(11) . ?
C23 H23 0.9300 . ?
C23 C24 1.390(10) . ?
C24 H24 0.9300 . ?
C25 H25 0.9800 . ?
C25 C26 1.520(9) . ?
C26 C27 1.383(9) . ?
C26 C31 1.387(10) . ?
C27 C28 1.389(9) . ?
C28 H28 0.9300 . ?
C28 C29 1.414(10) . ?
C29 H29 0.9300 . ?
C29 C30 1.386(11) . ?
C30 H30 0.9300 . ?
C30 C31 1.393(10) . ?
C31 H31 0.9300 . ?

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
C7 O2 C6 115.4(5) . . ?
C2 C1 C6 117.7(6) . . ?
C2 C1 C9 121.7(7) . . ?
C6 C1 C9 120.7(6) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(7) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(7) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(7) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.9 . . ?
C6 C5 C4 118.1(7) . . ?
C6 C5 H5 120.9 . . ?
O2 C6 C1 122.4(6) . . ?
C5 C6 O2 115.4(6) . . ?
C5 C6 C1 122.2(7) . . ?
O2 C7 C8 127.7(6) . . ?
O2 C7 C12 120.5(6) . . ?
C8 C7 C12 111.7(6) . . ?
C7 C8 C9 120.5(6) . . ?
C7 C8 C10 111.2(6) . . ?
C9 C8 C10 128.2(6) . . ?
O1 C9 C1 123.9(7) . . ?
O1 C9 C8 122.7(6) . . ?
C8 C9 C1 113.4(6) . . ?
C8 C10 H10 111.5 . . ?
C8 C10 C11 105.2(5) . . ?
C8 C10 C15 114.1(5) . . ?
C11 C10 H10 111.5 . . ?
C11 C10 C15 102.7(5) . . ?
C15 C10 H10 111.5 . . ?
C10 C11 H11 112.1 . . ?
C12 C11 C10 105.1(5) . . ?
C12 C11 H11 112.1 . . ?
C12 C11 C13 111.6(5) . . ?
C13 C11 C10 103.2(5) . . ?
C13 C11 H11 112.1 . . ?
O3 C12 C7 126.3(6) . . ?
O3 C12 C11 127.6(6) . . ?
C7 C12 C11 106.0(6) . . ?
C11 C13 H13 114.7 . . ?
C11 C13 C17 106.7(5) . . ?
C14 C13 C11 99.7(5) . . ?
C14 C13 H13 114.7 . . ?
C14 C13 C17 104.8(5) . . ?
C17 C13 H13 114.7 . . ?
C13 C14 H14A 112.9 . . ?
C13 C14 H14B 112.9 . . ?
C13 C14 C15 94.3(5) . . ?
H14A C14 H14B 110.3 . . ?
C15 C14 H14A 112.9 . . ?
C15 C14 H14B 112.9 . . ?
C10 C15 H15 115.0 . . ?
C14 C15 C10 101.1(5) . . ?
C14 C15 H15 115.0 . . ?
C16 C15 C10 106.2(5) . . ?
C16 C15 C14 103.0(5) . . ?
C16 C15 H15 115.0 . . ?
C15 C16 H16 109.2 . . ?
C15 C16 C17 103.7(5) . . ?
C15 C16 C25 117.0(5) . . ?
C17 C16 H16 109.2 . . ?
C17 C16 C25 108.3(5) . . ?
C25 C16 H16 109.2 . . ?
C13 C17 C16 102.3(5) . . ?
C13 C17 H17 108.4 . . ?
C13 C17 C18 118.6(5) . . ?
C16 C17 H17 108.4 . . ?
C16 C17 C18 110.2(5) . . ?
C18 C17 H17 108.4 . . ?
C17 C18 H18 112.3 . . ?
C19 C18 C17 105.9(5) . . ?
C19 C18 H18 112.3 . . ?
C27 C18 C17 107.6(5) . . ?
C27 C18 H18 112.3 . . ?
C27 C18 C19 106.0(5) . . ?
C20 C19 C18 113.5(6) . . ?
C20 C19 C24 120.5(6) . . ?
C24 C19 C18 126.0(6) . . ?
C19 C20 C21 120.7(6) . . ?
C19 C20 C25 113.4(6) . . ?
C21 C20 C25 125.9(6) . . ?
C20 C21 H21 120.4 . . ?
C20 C21 C22 119.2(7) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.8(7) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 119.4 . . ?
C22 C23 C24 121.3(7) . . ?
C24 C23 H23 119.4 . . ?
C19 C24 H24 120.8 . . ?
C23 C24 C19 118.5(7) . . ?
C23 C24 H24 120.8 . . ?
C16 C25 H25 112.1 . . ?
C20 C25 C16 103.3(5) . . ?
C20 C25 H25 112.1 . . ?
C20 C25 C26 106.0(5) . . ?
C26 C25 C16 110.9(5) . . ?
C26 C25 H25 112.1 . . ?
C27 C26 C25 113.6(6) . . ?
C27 C26 C31 120.0(6) . . ?
C31 C26 C25 126.4(6) . . ?
C26 C27 C18 113.7(6) . . ?
C26 C27 C28 121.0(6) . . ?
C28 C27 C18 125.4(6) . . ?
C27 C28 H28 120.4 . . ?
C27 C28 C29 119.3(7) . . ?
C29 C28 H28 120.4 . . ?
C28 C29 H29 120.4 . . ?
C30 C29 C28 119.2(7) . . ?
C30 C29 H29 120.4 . . ?
C29 C30 H30 119.6 . . ?
C29 C30 C31 120.9(7) . . ?
C31 C30 H30 119.6 . . ?
C26 C31 C30 119.7(7) . . ?
C26 C31 H31 120.2 . . ?
C30 C31 H31 120.2 . . ?

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
O2 C7 C8 C9 2.0(11) . . . . ?
O2 C7 C8 C10 178.2(6) . . . . ?
O2 C7 C12 O3 -7.4(11) . . . . ?
O2 C7 C12 C11 176.4(6) . . . . ?
C1 C2 C3 C4 -0.4(11) . . . . ?
C2 C1 C6 O2 -179.7(6) . . . . ?
C2 C1 C6 C5 0.5(10) . . . . ?
C2 C1 C9 O1 -0.7(10) . . . . ?
C2 C1 C9 C8 179.0(6) . . . . ?
C2 C3 C4 C5 0.6(11) . . . . ?
C3 C4 C5 C6 -0.1(11) . . . . ?
C4 C5 C6 O2 179.8(6) . . . . ?
C4 C5 C6 C1 -0.4(10) . . . . ?
C6 O2 C7 C8 -2.6(10) . . . . ?
C6 O2 C7 C12 173.2(6) . . . . ?
C6 C1 C2 C3 -0.1(10) . . . . ?
C6 C1 C9 O1 179.7(6) . . . . ?
C6 C1 C9 C8 -0.6(9) . . . . ?
C7 O2 C6 C1 1.6(9) . . . . ?
C7 O2 C6 C5 -178.6(6) . . . . ?
C7 C8 C9 O1 179.5(6) . . . . ?
C7 C8 C9 C1 -0.2(9) . . . . ?
C7 C8 C10 C11 3.8(7) . . . . ?
C7 C8 C10 C15 -107.9(7) . . . . ?
C8 C7 C12 O3 169.0(7) . . . . ?
C8 C7 C12 C11 -7.1(8) . . . . ?
C8 C10 C11 C12 -7.8(7) . . . . ?
C8 C10 C11 C13 -124.9(5) . . . . ?
C8 C10 C15 C14 81.5(6) . . . . ?
C8 C10 C15 C16 -171.3(5) . . . . ?
C9 C1 C2 C3 -179.7(7) . . . . ?
C9 C1 C6 O2 -0.1(10) . . . . ?
C9 C1 C6 C5 -179.9(6) . . . . ?
C9 C8 C10 C11 179.6(6) . . . . ?
C9 C8 C10 C15 67.9(8) . . . . ?
C10 C8 C9 O1 4.1(11) . . . . ?
C10 C8 C9 C1 -175.7(6) . . . . ?
C10 C11 C12 O3 -167.1(7) . . . . ?
C10 C11 C12 C7 8.9(7) . . . . ?
C10 C11 C13 C14 40.6(6) . . . . ?
C10 C11 C13 C17 -68.2(6) . . . . ?
C10 C15 C16 C17 -68.3(6) . . . . ?
C10 C15 C16 C25 172.6(5) . . . . ?
C11 C10 C15 C14 -31.7(6) . . . . ?
C11 C10 C15 C16 75.5(6) . . . . ?
C11 C13 C14 C15 -59.2(5) . . . . ?
C11 C13 C17 C16 75.4(6) . . . . ?
C11 C13 C17 C18 -163.1(6) . . . . ?
C12 C7 C8 C9 -174.2(6) . . . . ?
C12 C7 C8 C10 2.0(8) . . . . ?
C12 C11 C13 C14 -71.8(6) . . . . ?
C12 C11 C13 C17 179.4(5) . . . . ?
C13 C11 C12 O3 -55.9(9) . . . . ?
C13 C11 C12 C7 120.1(6) . . . . ?
C13 C14 C15 C10 55.9(5) . . . . ?
C13 C14 C15 C16 -53.8(5) . . . . ?
C13 C17 C18 C19 -169.9(6) . . . . ?
C13 C17 C18 C27 -56.9(7) . . . . ?
C14 C13 C17 C16 -29.7(6) . . . . ?
C14 C13 C17 C18 91.8(6) . . . . ?
C14 C15 C16 C17 37.6(6) . . . . ?
C14 C15 C16 C25 -81.6(6) . . . . ?
C15 C10 C11 C12 111.8(5) . . . . ?
C15 C10 C11 C13 -5.3(6) . . . . ?
C15 C16 C17 C13 -4.8(6) . . . . ?
C15 C16 C17 C18 -131.9(5) . . . . ?
C15 C16 C25 C20 -179.8(5) . . . . ?
C15 C16 C25 C26 67.1(7) . . . . ?
C16 C17 C18 C19 -52.5(6) . . . . ?
C16 C17 C18 C27 60.5(6) . . . . ?
C16 C25 C26 C27 56.6(7) . . . . ?
C16 C25 C26 C31 -124.3(7) . . . . ?
C17 C13 C14 C15 51.0(5) . . . . ?
C17 C16 C25 C20 63.6(6) . . . . ?
C17 C16 C25 C26 -49.6(7) . . . . ?
C17 C18 C19 C20 59.2(7) . . . . ?
C17 C18 C19 C24 -123.2(7) . . . . ?
C17 C18 C27 C26 -58.3(7) . . . . ?
C17 C18 C27 C28 122.5(6) . . . . ?
C18 C19 C20 C21 -179.5(6) . . . . ?
C18 C19 C20 C25 0.1(8) . . . . ?
C18 C19 C24 C23 -178.9(6) . . . . ?
C18 C27 C28 C29 178.5(6) . . . . ?
C19 C18 C27 C26 54.7(7) . . . . ?
C19 C18 C27 C28 -124.6(6) . . . . ?
C19 C20 C21 C22 -2.5(10) . . . . ?
C19 C20 C25 C16 -62.3(7) . . . . ?
C19 C20 C25 C26 54.3(7) . . . . ?
C20 C19 C24 C23 -1.4(9) . . . . ?
C20 C21 C22 C23 1.1(10) . . . . ?
C20 C25 C26 C27 -54.8(7) . . . . ?
C20 C25 C26 C31 124.3(7) . . . . ?
C21 C20 C25 C16 117.3(7) . . . . ?
C21 C20 C25 C26 -126.1(7) . . . . ?
C21 C22 C23 C24 0.1(10) . . . . ?
C22 C23 C24 C19 0.0(10) . . . . ?
C24 C19 C20 C21 2.6(9) . . . . ?
C24 C19 C20 C25 -177.7(6) . . . . ?
C25 C16 C17 C13 120.1(5) . . . . ?
C25 C16 C17 C18 -7.0(7) . . . . ?
C25 C20 C21 C22 177.9(6) . . . . ?
C25 C26 C27 C18 -0.1(7) . . . . ?
C25 C26 C27 C28 179.2(5) . . . . ?
C25 C26 C31 C30 -178.6(6) . . . . ?
C26 C27 C28 C29 -0.7(9) . . . . ?
C27 C18 C19 C20 -54.9(7) . . . . ?
C27 C18 C19 C24 122.7(7) . . . . ?
C27 C26 C31 C30 0.5(9) . . . . ?
C27 C28 C29 C30 0.8(10) . . . . ?
C28 C29 C30 C31 -0.3(10) . . . . ?
C29 C30 C31 C26 -0.3(10) . . . . ?
C31 C26 C27 C18 -179.3(6) . . . . ?
C31 C26 C27 C28 0.0(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.764
_oxdiff_exptl_absorpt_empirical_full_min 0.716
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.756(8)
2 0.244(8)

####################################################################### 
# 
# 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_86-25
_database_code_depnum_ccdc_archive 'CCDC 2056370'
loop_
_audit_author_name
_audit_author_address
'Han Wen-Yong'
;Zunyi Medical University
China
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;
_audit_creation_date             2020-08-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 O3'
_chemical_formula_sum            'C22 H20 O3'
_chemical_formula_weight         332.38
_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           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   11.4543(7)
_cell_length_b                   6.0539(5)
_cell_length_c                   23.3796(14)
_cell_angle_alpha                90
_cell_angle_beta                 102.119(6)
_cell_angle_gamma                90
_cell_volume                     1585.10(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3079
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.9940
_cell_measurement_theta_min      2.7820
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            6346
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.263
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  25.00   1.00    2.00    --  -11.43 -99.00 150.00   45
  2  ω    -57.00  22.00   1.00    2.00    --  -11.43 -19.00 -60.00   79
  3  ω    -22.00  48.00   1.00    2.00    --  -11.43  37.00 120.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0483280000
_diffrn_orient_matrix_UB_12      0.0202305000
_diffrn_orient_matrix_UB_13      -0.0238385000
_diffrn_orient_matrix_UB_21      -0.0190475000
_diffrn_orient_matrix_UB_22      -0.1110469000
_diffrn_orient_matrix_UB_23      0.0012967000
_diffrn_orient_matrix_UB_31      -0.0362408000
_diffrn_orient_matrix_UB_32      0.0314140000
_diffrn_orient_matrix_UB_33      0.0198038000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2382
_reflns_number_total             2775
_reflns_odcompleteness_completeness 99.02
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2775
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0412
_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)+(0.0361P)²+0.5484P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0951
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C19(H19A,H19B), C21(H21A,H21B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
;
_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 0.72025(9) -0.1603(2) 0.33302(5) 0.0228(3) Uani 1 1 d . . . . .
O2 O 0.87074(9) 0.3573(2) 0.43850(4) 0.0216(3) Uani 1 1 d . . . . .
O3 O 0.69316(9) 0.6764(2) 0.45552(5) 0.0249(3) Uani 1 1 d . . . . .
C1 C 0.89309(13) 0.0018(3) 0.39319(6) 0.0187(4) Uani 1 1 d . . . . .
C2 C 0.97076(14) -0.1708(3) 0.38665(7) 0.0235(4) Uani 1 1 d . . . . .
H2 H 0.942141 -0.290664 0.362931 0.028 Uiso 1 1 calc R U . . .
C3 C 1.08867(14) -0.1650(3) 0.41487(7) 0.0257(4) Uani 1 1 d . . . . .
H3 H 1.139198 -0.281280 0.410559 0.031 Uiso 1 1 calc R U . . .
C4 C 1.13263(14) 0.0152(3) 0.45001(7) 0.0236(4) Uani 1 1 d . . . . .
H4 H 1.212528 0.018036 0.469047 0.028 Uiso 1 1 calc R U . . .
C5 C 1.05933(13) 0.1890(3) 0.45689(7) 0.0221(4) Uani 1 1 d . . . . .
H5 H 1.089067 0.309834 0.479950 0.027 Uiso 1 1 calc R U . . .
C6 C 0.94006(13) 0.1799(3) 0.42865(6) 0.0190(4) Uani 1 1 d . . . . .
C7 C 0.75421(13) 0.3478(3) 0.41177(6) 0.0189(4) Uani 1 1 d . . . . .
C8 C 0.69891(13) 0.1857(3) 0.37733(6) 0.0179(4) Uani 1 1 d . . . . .
C9 C 0.76505(13) -0.0072(3) 0.36452(6) 0.0187(4) Uani 1 1 d . . . . .
C10 C 0.56829(13) 0.2364(3) 0.35568(6) 0.0175(4) Uani 1 1 d . . . . .
H10 H 0.546418 0.234916 0.312845 0.021 Uiso 1 1 calc R U . . .
C11 C 0.55257(13) 0.4713(3) 0.38052(6) 0.0179(4) Uani 1 1 d . . . . .
H11 H 0.529575 0.581424 0.349477 0.022 Uiso 1 1 calc R U . . .
C12 C 0.67122(13) 0.5253(3) 0.42065(6) 0.0196(4) Uani 1 1 d . . . . .
C13 C 0.45488(13) 0.4380(3) 0.41651(6) 0.0196(4) Uani 1 1 d . . . . .
H13 H 0.453562 0.552950 0.445888 0.024 Uiso 1 1 calc R U . . .
C14 C 0.48954(14) 0.2076(3) 0.44243(7) 0.0215(4) Uani 1 1 d . . . . .
H14A H 0.432406 0.149169 0.463814 0.026 Uiso 1 1 calc R U . . .
H14B H 0.569447 0.203378 0.466619 0.026 Uiso 1 1 calc R U . . .
C15 C 0.48142(13) 0.0949(3) 0.38269(6) 0.0200(4) Uani 1 1 d . . . . .
H15 H 0.500362 -0.063122 0.385065 0.024 Uiso 1 1 calc R U . . .
C16 C 0.34988(13) 0.1479(3) 0.35426(7) 0.0210(4) Uani 1 1 d . . . . .
H16 H 0.297808 0.043473 0.369012 0.025 Uiso 1 1 calc R U . . .
C17 C 0.33132(13) 0.3847(3) 0.37825(7) 0.0201(4) Uani 1 1 d . . . . .
H17 H 0.273187 0.374994 0.403505 0.024 Uiso 1 1 calc R U . . .
C18 C 0.27491(14) 0.5138(3) 0.32283(7) 0.0246(4) Uani 1 1 d . . . . .
H18 H 0.280097 0.674879 0.326640 0.030 Uiso 1 1 calc R U . . .
C19 C 0.33306(14) 0.4159(3) 0.27508(7) 0.0251(4) Uani 1 1 d . . . . .
H19A H 0.418096 0.445241 0.281789 0.030 Uiso 1 1 calc R U . . .
H19B H 0.294190 0.463208 0.236087 0.030 Uiso 1 1 calc R U . . .
C20 C 0.30506(14) 0.1746(3) 0.28753(7) 0.0245(4) Uani 1 1 d . . . . .
H20 H 0.335270 0.064529 0.263509 0.029 Uiso 1 1 calc R U . . .
C21 C 0.16771(14) 0.1893(3) 0.27765(8) 0.0318(5) Uani 1 1 d . . . . .
H21A H 0.135950 0.073462 0.298666 0.038 Uiso 1 1 calc R U . . .
H21B H 0.130941 0.179206 0.236394 0.038 Uiso 1 1 calc R U . . .
C22 C 0.14725(14) 0.4216(3) 0.30259(8) 0.0323(5) Uani 1 1 d . . . . .
H22A H 0.100078 0.514707 0.272655 0.039 Uiso 1 1 calc R U . . .
H22B H 0.107256 0.409628 0.335145 0.039 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 C9 1.227(2) . ?
O2 C6 1.383(2) . ?
O2 C7 1.3510(18) . ?
O3 C12 1.2162(19) . ?
C1 C2 1.402(2) . ?
C1 C6 1.397(2) . ?
C1 C9 1.480(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.395(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(2) . ?
C7 C8 1.341(2) . ?
C7 C12 1.478(2) . ?
C8 C9 1.457(2) . ?
C8 C10 1.507(2) . ?
C10 H10 0.9800 . ?
C10 C11 1.561(2) . ?
C10 C15 1.545(2) . ?
C11 H11 0.9800 . ?
C11 C12 1.516(2) . ?
C11 C13 1.548(2) . ?
C13 H13 0.9800 . ?
C13 C14 1.539(2) . ?
C13 C17 1.541(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.540(2) . ?
C15 H15 0.9800 . ?
C15 C16 1.547(2) . ?
C16 H16 0.9800 . ?
C16 C17 1.570(2) . ?
C16 C20 1.545(2) . ?
C17 H17 0.9800 . ?
C17 C18 1.535(2) . ?
C18 H18 0.9800 . ?
C18 C19 1.534(2) . ?
C18 C22 1.544(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.536(3) . ?
C20 H20 0.9800 . ?
C20 C21 1.544(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.558(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?

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
C7 O2 C6 115.86(12) . . ?
C2 C1 C9 120.97(15) . . ?
C6 C1 C2 117.78(14) . . ?
C6 C1 C9 121.24(15) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.74(16) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.99(16) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.88(15) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.56(16) . . ?
C6 C5 H5 120.7 . . ?
O2 C6 C1 122.33(14) . . ?
O2 C6 C5 115.62(14) . . ?
C5 C6 C1 122.05(15) . . ?
O2 C7 C12 120.43(14) . . ?
C8 C7 O2 127.21(15) . . ?
C8 C7 C12 112.32(14) . . ?
C7 C8 C9 120.63(14) . . ?
C7 C8 C10 111.27(14) . . ?
C9 C8 C10 128.09(14) . . ?
O1 C9 C1 123.32(15) . . ?
O1 C9 C8 123.96(14) . . ?
C8 C9 C1 112.72(14) . . ?
C8 C10 H10 111.4 . . ?
C8 C10 C11 104.17(12) . . ?
C8 C10 C15 115.39(13) . . ?
C11 C10 H10 111.4 . . ?
C15 C10 H10 111.4 . . ?
C15 C10 C11 102.63(12) . . ?
C10 C11 H11 112.2 . . ?
C12 C11 C10 105.56(12) . . ?
C12 C11 H11 112.2 . . ?
C12 C11 C13 110.37(12) . . ?
C13 C11 C10 103.70(13) . . ?
C13 C11 H11 112.2 . . ?
O3 C12 C7 126.35(14) . . ?
O3 C12 C11 127.53(15) . . ?
C7 C12 C11 106.01(13) . . ?
C11 C13 H13 114.1 . . ?
C14 C13 C11 100.12(12) . . ?
C14 C13 H13 114.1 . . ?
C14 C13 C17 99.68(13) . . ?
C17 C13 C11 113.11(12) . . ?
C17 C13 H13 114.1 . . ?
C13 C14 H14A 112.8 . . ?
C13 C14 H14B 112.8 . . ?
C13 C14 C15 94.76(12) . . ?
H14A C14 H14B 110.2 . . ?
C15 C14 H14A 112.8 . . ?
C15 C14 H14B 112.8 . . ?
C10 C15 H15 114.2 . . ?
C10 C15 C16 111.24(13) . . ?
C14 C15 C10 101.75(13) . . ?
C14 C15 H15 114.2 . . ?
C14 C15 C16 99.54(12) . . ?
C16 C15 H15 114.2 . . ?
C15 C16 H16 109.0 . . ?
C15 C16 C17 103.20(12) . . ?
C17 C16 H16 109.0 . . ?
C20 C16 C15 122.85(13) . . ?
C20 C16 H16 109.0 . . ?
C20 C16 C17 102.94(13) . . ?
C13 C17 C16 102.81(12) . . ?
C13 C17 H17 108.7 . . ?
C16 C17 H17 108.7 . . ?
C18 C17 C13 123.77(14) . . ?
C18 C17 C16 103.17(12) . . ?
C18 C17 H17 108.7 . . ?
C17 C18 H18 115.0 . . ?
C17 C18 C22 106.18(15) . . ?
C19 C18 C17 104.33(13) . . ?
C19 C18 H18 115.0 . . ?
C19 C18 C22 99.50(13) . . ?
C22 C18 H18 115.0 . . ?
C18 C19 H19A 112.7 . . ?
C18 C19 H19B 112.7 . . ?
C18 C19 C20 95.15(13) . . ?
H19A C19 H19B 110.2 . . ?
C20 C19 H19A 112.7 . . ?
C20 C19 H19B 112.7 . . ?
C16 C20 H20 115.1 . . ?
C19 C20 C16 104.62(13) . . ?
C19 C20 H20 115.1 . . ?
C19 C20 C21 99.40(14) . . ?
C21 C20 C16 105.62(13) . . ?
C21 C20 H20 115.1 . . ?
C20 C21 H21A 111.2 . . ?
C20 C21 H21B 111.2 . . ?
C20 C21 C22 102.99(14) . . ?
H21A C21 H21B 109.1 . . ?
C22 C21 H21A 111.2 . . ?
C22 C21 H21B 111.2 . . ?
C18 C22 C21 103.52(13) . . ?
C18 C22 H22A 111.1 . . ?
C18 C22 H22B 111.1 . . ?
C21 C22 H22A 111.1 . . ?
C21 C22 H22B 111.1 . . ?
H22A C22 H22B 109.0 . . ?

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 C7 C8 C9 -0.6(2) . . . . ?
O2 C7 C8 C10 -179.87(13) . . . . ?
O2 C7 C12 O3 -8.3(2) . . . . ?
O2 C7 C12 C11 175.18(13) . . . . ?
C1 C2 C3 C4 -0.7(2) . . . . ?
C2 C1 C6 O2 -179.24(13) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
C2 C1 C9 O1 -1.5(2) . . . . ?
C2 C1 C9 C8 179.07(13) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C4 C5 C6 O2 178.52(13) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C6 O2 C7 C8 0.5(2) . . . . ?
C6 O2 C7 C12 178.20(13) . . . . ?
C6 C1 C2 C3 0.8(2) . . . . ?
C6 C1 C9 O1 179.90(14) . . . . ?
C6 C1 C9 C8 0.5(2) . . . . ?
C7 O2 C6 C1 0.1(2) . . . . ?
C7 O2 C6 C5 -179.10(13) . . . . ?
C7 C8 C9 O1 -179.35(15) . . . . ?
C7 C8 C9 C1 0.1(2) . . . . ?
C7 C8 C10 C11 3.09(16) . . . . ?
C7 C8 C10 C15 -108.59(16) . . . . ?
C8 C7 C12 O3 169.70(15) . . . . ?
C8 C7 C12 C11 -6.77(17) . . . . ?
C8 C10 C11 C12 -6.91(14) . . . . ?
C8 C10 C11 C13 -123.00(12) . . . . ?
C8 C10 C15 C14 79.03(16) . . . . ?
C8 C10 C15 C16 -175.75(13) . . . . ?
C9 C1 C2 C3 -177.88(14) . . . . ?
C9 C1 C6 O2 -0.6(2) . . . . ?
C9 C1 C6 C5 178.60(14) . . . . ?
C9 C8 C10 C11 -176.13(14) . . . . ?
C9 C8 C10 C15 72.18(19) . . . . ?
C10 C8 C9 O1 -0.2(2) . . . . ?
C10 C8 C9 C1 179.24(14) . . . . ?
C10 C11 C12 O3 -168.23(15) . . . . ?
C10 C11 C12 C7 8.19(15) . . . . ?
C10 C11 C13 C14 37.27(14) . . . . ?
C10 C11 C13 C17 -67.91(16) . . . . ?
C10 C15 C16 C17 -70.96(15) . . . . ?
C10 C15 C16 C20 44.2(2) . . . . ?
C11 C10 C15 C14 -33.55(14) . . . . ?
C11 C10 C15 C16 71.66(14) . . . . ?
C11 C13 C14 C15 -56.80(13) . . . . ?
C11 C13 C17 C16 68.41(16) . . . . ?
C11 C13 C17 C18 -47.3(2) . . . . ?
C12 C7 C8 C9 -178.47(13) . . . . ?
C12 C7 C8 C10 2.25(18) . . . . ?
C12 C11 C13 C14 -75.37(15) . . . . ?
C12 C11 C13 C17 179.45(14) . . . . ?
C13 C11 C12 O3 -56.8(2) . . . . ?
C13 C11 C12 C7 119.64(14) . . . . ?
C13 C14 C15 C10 56.02(13) . . . . ?
C13 C14 C15 C16 -58.19(13) . . . . ?
C13 C17 C18 C19 81.40(18) . . . . ?
C13 C17 C18 C22 -174.04(14) . . . . ?
C14 C13 C17 C16 -37.04(13) . . . . ?
C14 C13 C17 C18 -152.72(15) . . . . ?
C14 C15 C16 C17 35.71(15) . . . . ?
C14 C15 C16 C20 150.87(16) . . . . ?
C15 C10 C11 C12 113.74(12) . . . . ?
C15 C10 C11 C13 -2.34(14) . . . . ?
C15 C16 C17 C13 0.79(14) . . . . ?
C15 C16 C17 C18 130.48(13) . . . . ?
C15 C16 C20 C19 -84.23(18) . . . . ?
C15 C16 C20 C21 171.41(15) . . . . ?
C16 C17 C18 C19 -34.10(16) . . . . ?
C16 C17 C18 C22 70.47(15) . . . . ?
C16 C20 C21 C22 71.38(17) . . . . ?
C17 C13 C14 C15 58.97(12) . . . . ?
C17 C16 C20 C19 31.07(15) . . . . ?
C17 C16 C20 C21 -73.29(16) . . . . ?
C17 C18 C19 C20 51.66(15) . . . . ?
C17 C18 C22 C21 -72.66(16) . . . . ?
C18 C19 C20 C16 -50.42(14) . . . . ?
C18 C19 C20 C21 58.56(13) . . . . ?
C19 C18 C22 C21 35.39(17) . . . . ?
C19 C20 C21 C22 -36.80(16) . . . . ?
C20 C16 C17 C13 -127.94(12) . . . . ?
C20 C16 C17 C18 1.76(15) . . . . ?
C20 C21 C22 C18 0.89(17) . . . . ?
C22 C18 C19 C20 -57.87(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.587
_oxdiff_exptl_absorpt_empirical_full_min 0.801
####################################################################### 
# 
# 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_86-36
_database_code_depnum_ccdc_archive 'CCDC 2056371'
loop_
_audit_author_name
_audit_author_address
'Han Wen-Yong'
;Zunyi Medical University
China
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;
_audit_creation_date             2020-08-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H20 O3'
_chemical_formula_sum            'C25 H20 O3'
_chemical_formula_weight         368.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   7.2707(6)
_cell_length_b                   43.553(5)
_cell_length_c                   5.7823(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.002(8)
_cell_angle_gamma                90
_cell_volume                     1821.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2047
_cell_measurement_temperature    99.98(11)
_cell_measurement_theta_max      73.5150
_cell_measurement_theta_min      2.1040
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_unetI/netI     0.0812
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_k_min       -53
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7718
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.649
_diffrn_reflns_theta_min         4.060
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5368
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      5.00  82.00   1.00    1.00    --   40.73 -99.00 -30.00   77
  2  ω     27.00  64.00   1.00    1.00    --   40.73-125.00 -90.00   37
  3  ω     25.00 105.00   1.00    2.00    --  107.58 -94.00-150.00   80
  4  ω     83.00 132.00   1.00    2.00    --  107.58 -45.00-180.00   49
  5  ω     94.00 136.00   1.00    2.00    --  107.58 -15.00-180.00   42
  6  ω    114.00 161.00   1.00    2.00    --  107.58  61.00   0.00   47
  7  ω     78.00 118.00   1.00    2.00    --  107.58  61.00  60.00   40
  8  ω     36.00 134.00   1.00    2.00    --  107.58 -30.00  30.00   98
  9  ω     28.00  91.00   1.00    2.00    --  107.58 -15.00-180.00   63
 10  ω    -74.00  -3.00   1.00    1.00    --  -40.73 125.00  60.00   71
 11  ω   -115.00 -83.00   1.00    1.00    --  -40.73 -37.00   0.00   32
 12  ω    -37.00 -11.00   1.00    5.00    --  -41.23 125.00 -60.00   26
 13  ω     18.00 112.00   1.00    5.00    --   41.23  37.00  90.00   94
 14  ω    -32.00 -19.00   1.00   10.00    --   41.23 -37.00  90.00   13
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1716489000
_diffrn_orient_matrix_UB_12      0.0083116000
_diffrn_orient_matrix_UB_13      0.1690243000
_diffrn_orient_matrix_UB_21      0.0875580000
_diffrn_orient_matrix_UB_22      0.0275555000
_diffrn_orient_matrix_UB_23      -0.1065621000
_diffrn_orient_matrix_UB_31      -0.1862237000
_diffrn_orient_matrix_UB_32      0.0205827000
_diffrn_orient_matrix_UB_33      0.0740395000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2563
_reflns_number_total             3542
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3542
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0846
_refine_ls_restrained_S_all      1.033
_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)+(0.1136P)²+3.3488P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2269
_refine_ls_wR_factor_ref         0.2450
_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), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.4151(4) -0.44785(6) -0.8626(4) 0.0245(6) Uani 1 1 d . . . . .
O2 O -0.1413(3) -0.46752(5) -0.2150(4) 0.0212(6) Uani 1 1 d . . . . .
O3 O -0.0148(4) -0.41190(6) 0.0302(4) 0.0281(6) Uani 1 1 d . . . . .
C1 C -0.2862(5) -0.48542(8) -0.5901(6) 0.0197(7) Uani 1 1 d . . . . .
C2 C -0.3288(5) -0.51091(8) -0.7347(6) 0.0223(8) Uani 1 1 d . . . . .
H2 H -0.386813 -0.507890 -0.884026 0.027 Uiso 1 1 calc R U . . .
C3 C -0.2863(5) -0.54026(8) -0.6592(7) 0.0240(8) Uani 1 1 d . . . . .
H3 H -0.313742 -0.556819 -0.758352 0.029 Uiso 1 1 calc R U . . .
C4 C -0.2021(5) -0.54523(8) -0.4345(6) 0.0224(8) Uani 1 1 d . . . . .
H4 H -0.176969 -0.565153 -0.382557 0.027 Uiso 1 1 calc R U . . .
C5 C -0.1558(5) -0.52059(8) -0.2884(6) 0.0215(8) Uani 1 1 d . . . . .
H5 H -0.097279 -0.523781 -0.139537 0.026 Uiso 1 1 calc R U . . .
C6 C -0.1980(5) -0.49105(8) -0.3674(6) 0.0201(7) Uani 1 1 d . . . . .
C7 C -0.3338(5) -0.45396(8) -0.6699(6) 0.0199(7) Uani 1 1 d . . . . .
C8 C -0.2677(5) -0.43066(8) -0.5002(6) 0.0199(7) Uani 1 1 d . . . . .
C9 C -0.1762(5) -0.43886(8) -0.2951(6) 0.0208(7) Uani 1 1 d . . . . .
C10 C -0.1044(5) -0.41182(8) -0.1595(6) 0.0217(7) Uani 1 1 d . . . . .
C11 C -0.1643(5) -0.38382(8) -0.3063(6) 0.0205(7) Uani 1 1 d . . . . .
H11 H -0.057386 -0.372198 -0.348680 0.025 Uiso 1 1 calc R U . . .
C12 C -0.2826(5) -0.39649(8) -0.5253(6) 0.0222(8) Uani 1 1 d . . . . .
H12 H -0.235030 -0.389464 -0.668684 0.027 Uiso 1 1 calc R U . . .
C13 C -0.4779(5) -0.38309(8) -0.5017(6) 0.0214(8) Uani 1 1 d . . . . .
H13 H -0.580982 -0.394316 -0.585750 0.026 Uiso 1 1 calc R U . . .
C14 C -0.4796(5) -0.38183(8) -0.2367(6) 0.0214(8) Uani 1 1 d . . . . .
H14A H -0.469819 -0.401996 -0.165245 0.026 Uiso 1 1 calc R U . . .
H14B H -0.586537 -0.371072 -0.190074 0.026 Uiso 1 1 calc R U . . .
C15 C -0.2999(5) -0.36302(8) -0.1904(6) 0.0217(8) Uani 1 1 d . . . . .
H15 H -0.263062 -0.358087 -0.026789 0.026 Uiso 1 1 calc R U . . .
C16 C -0.3358(5) -0.33512(8) -0.3521(6) 0.0234(8) Uani 1 1 d . . . . .
H16 H -0.225143 -0.324313 -0.392042 0.028 Uiso 1 1 calc R U . . .
C17 C -0.4646(5) -0.34902(8) -0.5655(6) 0.0239(8) Uani 1 1 d . . . . .
H17 H -0.421831 -0.345148 -0.718032 0.029 Uiso 1 1 calc R U . . .
C18 C -0.6125(5) -0.32706(8) -0.4999(7) 0.0253(8) Uani 1 1 d . . . . .
C19 C -0.5008(5) -0.31477(8) -0.3148(6) 0.0238(8) Uani 1 1 d . . . . .
C20 C -0.5572(6) -0.29187(8) -0.1700(7) 0.0265(8) Uani 1 1 d . . . . .
C21 C -0.7394(6) -0.28196(8) -0.2304(7) 0.0291(9) Uani 1 1 d . . . . .
H21 H -0.786907 -0.266565 -0.142269 0.035 Uiso 1 1 calc R U . . .
C22 C -0.8523(5) -0.29428(8) -0.4176(7) 0.0279(9) Uani 1 1 d . . . . .
H22 H -0.971666 -0.286611 -0.449655 0.033 Uiso 1 1 calc R U . . .
C23 C -0.7942(5) -0.31763(8) -0.5593(7) 0.0257(8) Uani 1 1 d . . . . .
C24 C -0.9149(6) -0.33064(9) -0.7622(7) 0.0311(9) Uani 1 1 d . . . . .
H24A H -0.920666 -0.352567 -0.747380 0.047 Uiso 1 1 calc R U . . .
H24B H -0.864062 -0.325487 -0.903913 0.047 Uiso 1 1 calc R U . . .
H24C H -1.037061 -0.322201 -0.765137 0.047 Uiso 1 1 calc R U . . .
C25 C -0.4346(6) -0.27849(9) 0.0292(7) 0.0335(9) Uani 1 1 d . . . . .
H25A H -0.309642 -0.285151 0.020749 0.050 Uiso 1 1 calc R U . . .
H25B H -0.475702 -0.285244 0.173216 0.050 Uiso 1 1 calc R U . . .
H25C H -0.439987 -0.256482 0.021132 0.050 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 C7 1.235(4) . ?
O2 C6 1.386(4) . ?
O2 C9 1.346(4) . ?
O3 C10 1.216(4) . ?
C1 C2 1.405(5) . ?
C1 C6 1.399(5) . ?
C1 C7 1.475(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.394(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(5) . ?
C7 C8 1.458(5) . ?
C8 C9 1.346(5) . ?
C8 C12 1.498(5) . ?
C9 C10 1.479(5) . ?
C10 C11 1.523(5) . ?
C11 H11 0.9800 . ?
C11 C12 1.556(5) . ?
C11 C15 1.543(5) . ?
C12 H12 0.9800 . ?
C12 C13 1.554(5) . ?
C13 H13 0.9800 . ?
C13 C14 1.535(5) . ?
C13 C17 1.534(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.541(5) . ?
C15 H15 0.9800 . ?
C15 C16 1.539(5) . ?
C16 H16 0.9800 . ?
C16 C17 1.589(5) . ?
C16 C19 1.525(5) . ?
C17 H17 0.9800 . ?
C17 C18 1.517(5) . ?
C18 C19 1.382(5) . ?
C18 C23 1.392(6) . ?
C19 C20 1.391(5) . ?
C20 C21 1.403(6) . ?
C20 C25 1.499(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.396(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.399(5) . ?
C23 C24 1.501(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C9 O2 C6 115.7(3) . . ?
C2 C1 C7 121.2(3) . . ?
C6 C1 C2 117.4(3) . . ?
C6 C1 C7 121.4(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(3) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.1(3) . . ?
C6 C5 H5 120.5 . . ?
O2 C6 C1 122.2(3) . . ?
O2 C6 C5 115.8(3) . . ?
C5 C6 C1 122.0(3) . . ?
O1 C7 C1 123.8(3) . . ?
O1 C7 C8 123.4(3) . . ?
C8 C7 C1 112.7(3) . . ?
C7 C8 C12 127.7(3) . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 C12 111.9(3) . . ?
O2 C9 C8 127.4(3) . . ?
O2 C9 C10 120.8(3) . . ?
C8 C9 C10 111.7(3) . . ?
O3 C10 C9 127.0(3) . . ?
O3 C10 C11 126.9(3) . . ?
C9 C10 C11 106.1(3) . . ?
C10 C11 H11 111.4 . . ?
C10 C11 C12 105.7(3) . . ?
C10 C11 C15 112.7(3) . . ?
C12 C11 H11 111.4 . . ?
C15 C11 H11 111.4 . . ?
C15 C11 C12 103.7(3) . . ?
C8 C12 C11 104.2(3) . . ?
C8 C12 H12 111.3 . . ?
C8 C12 C13 115.0(3) . . ?
C11 C12 H12 111.3 . . ?
C13 C12 C11 103.2(3) . . ?
C13 C12 H12 111.3 . . ?
C12 C13 H13 115.3 . . ?
C14 C13 C12 101.8(3) . . ?
C14 C13 H13 115.3 . . ?
C14 C13 C17 102.3(3) . . ?
C17 C13 C12 105.1(3) . . ?
C17 C13 H13 115.3 . . ?
C13 C14 H14A 112.6 . . ?
C13 C14 H14B 112.6 . . ?
C13 C14 C15 95.6(3) . . ?
H14A C14 H14B 110.1 . . ?
C15 C14 H14A 112.6 . . ?
C15 C14 H14B 112.6 . . ?
C11 C15 C14 100.4(3) . . ?
C11 C15 H15 115.2 . . ?
C14 C15 H15 115.2 . . ?
C16 C15 C11 106.0(3) . . ?
C16 C15 C14 103.2(3) . . ?
C16 C15 H15 115.2 . . ?
C15 C16 H16 115.6 . . ?
C15 C16 C17 102.7(3) . . ?
C17 C16 H16 115.6 . . ?
C19 C16 C15 117.3(3) . . ?
C19 C16 H16 115.6 . . ?
C19 C16 C17 85.6(3) . . ?
C13 C17 C16 103.2(3) . . ?
C13 C17 H17 114.6 . . ?
C16 C17 H17 114.6 . . ?
C18 C17 C13 119.0(3) . . ?
C18 C17 C16 86.6(3) . . ?
C18 C17 H17 114.6 . . ?
C19 C18 C17 93.6(3) . . ?
C19 C18 C23 122.9(4) . . ?
C23 C18 C17 143.5(4) . . ?
C18 C19 C16 94.2(3) . . ?
C18 C19 C20 123.9(4) . . ?
C20 C19 C16 141.9(4) . . ?
C19 C20 C21 113.6(4) . . ?
C19 C20 C25 123.5(4) . . ?
C21 C20 C25 122.8(3) . . ?
C20 C21 H21 118.7 . . ?
C22 C21 C20 122.6(4) . . ?
C22 C21 H21 118.7 . . ?
C21 C22 H22 118.5 . . ?
C21 C22 C23 123.0(4) . . ?
C23 C22 H22 118.5 . . ?
C18 C23 C22 114.0(4) . . ?
C18 C23 C24 122.9(3) . . ?
C22 C23 C24 123.0(4) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C20 C25 H25A 109.5 . . ?
C20 C25 H25B 109.5 . . ?
C20 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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 C7 C8 C9 -178.4(3) . . . . ?
O1 C7 C8 C12 -0.6(6) . . . . ?
O2 C9 C10 O3 -1.7(6) . . . . ?
O2 C9 C10 C11 177.9(3) . . . . ?
O3 C10 C11 C12 -177.4(3) . . . . ?
O3 C10 C11 C15 -64.7(5) . . . . ?
C1 C2 C3 C4 1.1(5) . . . . ?
C1 C7 C8 C9 -0.8(5) . . . . ?
C1 C7 C8 C12 177.0(3) . . . . ?
C2 C1 C6 O2 176.6(3) . . . . ?
C2 C1 C6 C5 -1.0(5) . . . . ?
C2 C1 C7 O1 1.2(5) . . . . ?
C2 C1 C7 C8 -176.3(3) . . . . ?
C2 C3 C4 C5 -1.9(5) . . . . ?
C3 C4 C5 C6 1.4(5) . . . . ?
C4 C5 C6 O2 -177.6(3) . . . . ?
C4 C5 C6 C1 0.1(5) . . . . ?
C6 O2 C9 C8 3.7(5) . . . . ?
C6 O2 C9 C10 -173.3(3) . . . . ?
C6 C1 C2 C3 0.4(5) . . . . ?
C6 C1 C7 O1 -178.4(3) . . . . ?
C6 C1 C7 C8 4.0(4) . . . . ?
C7 C1 C2 C3 -179.3(3) . . . . ?
C7 C1 C6 O2 -3.7(5) . . . . ?
C7 C1 C6 C5 178.7(3) . . . . ?
C7 C8 C9 O2 -3.2(5) . . . . ?
C7 C8 C9 C10 174.0(3) . . . . ?
C7 C8 C12 C11 -172.2(3) . . . . ?
C7 C8 C12 C13 75.7(4) . . . . ?
C8 C9 C10 O3 -179.1(4) . . . . ?
C8 C9 C10 C11 0.5(4) . . . . ?
C8 C12 C13 C14 81.0(3) . . . . ?
C8 C12 C13 C17 -172.7(3) . . . . ?
C9 O2 C6 C1 -0.1(4) . . . . ?
C9 O2 C6 C5 177.6(3) . . . . ?
C9 C8 C12 C11 5.8(4) . . . . ?
C9 C8 C12 C13 -106.4(4) . . . . ?
C9 C10 C11 C12 3.0(4) . . . . ?
C9 C10 C11 C15 115.7(3) . . . . ?
C10 C11 C12 C8 -5.1(3) . . . . ?
C10 C11 C12 C13 115.3(3) . . . . ?
C10 C11 C15 C14 -76.5(3) . . . . ?
C10 C11 C15 C16 176.4(3) . . . . ?
C11 C12 C13 C14 -31.8(3) . . . . ?
C11 C12 C13 C17 74.6(3) . . . . ?
C11 C15 C16 C17 73.3(3) . . . . ?
C11 C15 C16 C19 164.8(3) . . . . ?
C12 C8 C9 O2 178.7(3) . . . . ?
C12 C8 C9 C10 -4.1(4) . . . . ?
C12 C11 C15 C14 37.4(3) . . . . ?
C12 C11 C15 C16 -69.7(3) . . . . ?
C12 C13 C14 C15 54.2(3) . . . . ?
C12 C13 C17 C16 -70.2(3) . . . . ?
C12 C13 C17 C18 -163.7(3) . . . . ?
C13 C14 C15 C11 -56.2(3) . . . . ?
C13 C14 C15 C16 53.1(3) . . . . ?
C13 C17 C18 C19 103.6(4) . . . . ?
C13 C17 C18 C23 -75.8(6) . . . . ?
C14 C13 C17 C16 35.7(3) . . . . ?
C14 C13 C17 C18 -57.8(4) . . . . ?
C14 C15 C16 C17 -31.8(3) . . . . ?
C14 C15 C16 C19 59.7(4) . . . . ?
C15 C11 C12 C8 -124.0(3) . . . . ?
C15 C11 C12 C13 -3.6(3) . . . . ?
C15 C16 C17 C13 -2.3(3) . . . . ?
C15 C16 C17 C18 116.7(3) . . . . ?
C15 C16 C19 C18 -101.7(3) . . . . ?
C15 C16 C19 C20 77.4(6) . . . . ?
C16 C17 C18 C19 0.3(3) . . . . ?
C16 C17 C18 C23 -179.1(5) . . . . ?
C16 C19 C20 C21 -179.6(4) . . . . ?
C16 C19 C20 C25 1.6(7) . . . . ?
C17 C13 C14 C15 -54.4(3) . . . . ?
C17 C16 C19 C18 0.3(3) . . . . ?
C17 C16 C19 C20 179.4(5) . . . . ?
C17 C18 C19 C16 -0.3(3) . . . . ?
C17 C18 C19 C20 -179.7(3) . . . . ?
C17 C18 C23 C22 -179.7(5) . . . . ?
C17 C18 C23 C24 -1.6(8) . . . . ?
C18 C19 C20 C21 -0.7(5) . . . . ?
C18 C19 C20 C25 -179.5(3) . . . . ?
C19 C16 C17 C13 -119.3(3) . . . . ?
C19 C16 C17 C18 -0.3(2) . . . . ?
C19 C18 C23 C22 1.0(5) . . . . ?
C19 C18 C23 C24 179.1(3) . . . . ?
C19 C20 C21 C22 0.5(5) . . . . ?
C20 C21 C22 C23 0.5(6) . . . . ?
C21 C22 C23 C18 -1.2(5) . . . . ?
C21 C22 C23 C24 -179.3(4) . . . . ?
C23 C18 C19 C16 179.2(3) . . . . ?
C23 C18 C19 C20 -0.1(6) . . . . ?
C25 C20 C21 C22 179.3(4) . . . . ?

_olex2_date_sample_data_collection 2020-08-26
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.646
_oxdiff_exptl_absorpt_empirical_full_min 0.455
####################################################################### 
# 
# 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_86-32
_database_code_depnum_ccdc_archive 'CCDC 2056367'
loop_
_audit_author_name
_audit_author_address
'Han Wen-Yong'
;Zunyi Medical University
China
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;
_audit_creation_date             2020-08-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 O3'
_chemical_formula_sum            'C21 H14 O3'
_chemical_formula_weight         314.32
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8572(6)
_cell_length_b                   8.3393(9)
_cell_length_c                   14.637(2)
_cell_angle_alpha                93.034(10)
_cell_angle_beta                 96.799(10)
_cell_angle_gamma                90.121(9)
_cell_volume                     708.92(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1267
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6800
_cell_measurement_theta_min      7.6110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0859
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2748
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.443
_diffrn_reflns_theta_min         3.045
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  34.00   1.00    2.00    --  -40.73  37.00  30.00   99
  2  ω    -82.00  20.00   1.00    2.00    --  -40.73  19.00 -30.00  102
  3  ω     26.00  92.00   1.00    2.00    --   40.73-125.00 120.00   66
  4  ω     43.00 101.00   1.00    3.00    --  108.20 -94.00   0.00   58
  5  ω     59.00  86.00   1.00    3.00    --  108.20 -94.00  90.00   27
  6  ω     34.00 114.00   1.00    3.00    --  108.20 -30.00  90.00   80
  7  ω     84.00 173.00   1.00    3.00    --  108.20  30.00  30.00   89
  8  ω    111.00 178.00   1.00    3.00    --  108.20  30.00 -90.00   67
  9  ω    140.00 178.00   1.00    3.00    --  108.20 125.00  90.00   38
 10  ω    102.00 129.00   1.00    3.00    --  108.20 125.00  90.00   27
 11  ω     50.00 129.00   1.00    3.00    --  108.20 -45.00 -30.00   79
 12  ω     63.00  90.00   1.00    2.00    --   40.73-122.00-149.00   27
 13  ω     33.00  92.00   1.00    3.00    --  108.20 -94.00-120.00   59
 14  ω     35.00 134.00   1.00    3.00    --  108.20 -45.00-150.00   99
 15  ω     28.00 102.00   1.00    3.00    --  108.20 -94.00 150.00   74
 16  ω   -112.00 -64.00   1.00    2.00    --  -40.73-150.00  48.00   48
 17  ω    109.00 134.00   1.00   10.00    --  108.20 -45.00 -30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0471415000
_diffrn_orient_matrix_UB_12      -0.1684510000
_diffrn_orient_matrix_UB_13      0.0360287000
_diffrn_orient_matrix_UB_21      0.0436499000
_diffrn_orient_matrix_UB_22      0.0738277000
_diffrn_orient_matrix_UB_23      0.0992912000
_diffrn_orient_matrix_UB_31      -0.2569841000
_diffrn_orient_matrix_UB_32      -0.0199734000
_diffrn_orient_matrix_UB_33      0.0104917000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2157
_reflns_number_total             2748
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.127
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2748
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1374
_refine_ls_R_factor_gt           0.1202
_refine_ls_restrained_S_all      1.052
_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)+(0.0140P)²+6.2452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2766
_refine_ls_wR_factor_ref         0.2844
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.572(7)
 0.428(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C18(H18), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 -0.3165(8) -0.8927(6) -0.7685(3) 0.0242(10) Uani 1 1 d . . . . .
O2 O -0.8550(7) -0.9171(5) -0.6109(3) 0.0209(10) Uani 1 1 d . . . . .
O3 O -1.1262(8) -0.6301(5) -0.6153(3) 0.0246(11) Uani 1 1 d . . . . .
C1 C -0.5056(11) -1.0316(8) -0.6603(4) 0.0189(13) Uani 1 1 d . . . . .
C2 C -0.3448(11) -1.1559(8) -0.6511(5) 0.0234(14) Uani 1 1 d . . . . .
H2 H -0.221157 -1.157288 -0.685590 0.028 Uiso 1 1 calc R U . . .
C3 C -0.3682(12) -1.2762(8) -0.5915(5) 0.0238(14) Uani 1 1 d . . . . .
H3 H -0.259608 -1.357302 -0.585442 0.029 Uiso 1 1 calc R U . . .
C4 C -0.5551(11) -1.2763(8) -0.5401(4) 0.0216(14) Uani 1 1 d . . . . .
H4 H -0.570073 -1.357548 -0.500084 0.026 Uiso 1 1 calc R U . . .
C5 C -0.7177(11) -1.1562(7) -0.5486(4) 0.0208(13) Uani 1 1 d . . . . .
H5 H -0.842851 -1.156493 -0.514991 0.025 Uiso 1 1 calc R U . . .
C6 C -0.6907(11) -1.0350(7) -0.6082(4) 0.0182(13) Uani 1 1 d . . . . .
C7 C -0.8154(10) -0.7908(7) -0.6602(4) 0.0175(12) Uani 1 1 d . . . . .
C8 C -0.6426(11) -0.7723(8) -0.7117(4) 0.0203(13) Uani 1 1 d . . . . .
C9 C -0.4738(11) -0.8964(8) -0.7197(4) 0.0216(13) Uani 1 1 d . . . . .
C10 C -0.9660(11) -0.6492(8) -0.6583(4) 0.0190(13) Uani 1 1 d . . . . .
C11 C -0.8675(10) -0.5275(7) -0.7175(4) 0.0166(12) Uani 1 1 d . . . . .
H11 H -0.827701 -0.426196 -0.682112 0.020 Uiso 1 1 calc R U . . .
C12 C -0.6491(10) -0.6077(7) -0.7522(4) 0.0187(13) Uani 1 1 d . . . . .
H12 H -0.509381 -0.545197 -0.730682 0.022 Uiso 1 1 calc R U . . .
C13 C -0.7036(11) -0.6106(7) -0.8588(4) 0.0193(13) Uani 1 1 d . . . . .
H13 H -0.610255 -0.682757 -0.893933 0.023 Uiso 1 1 calc R U . . .
C14 C -0.9672(11) -0.6453(8) -0.8711(4) 0.0226(14) Uani 1 1 d . . . . .
H14A H -1.036818 -0.639662 -0.934369 0.027 Uiso 1 1 calc R U . . .
H14B H -1.006579 -0.746289 -0.846662 0.027 Uiso 1 1 calc R U . . .
C15 C -1.0203(11) -0.4980(8) -0.8093(4) 0.0221(14) Uani 1 1 d . . . . .
H15 H -1.183636 -0.480420 -0.803829 0.027 Uiso 1 1 calc R U . . .
C16 C -0.9002(11) -0.3643(7) -0.8524(4) 0.0184(13) Uani 1 1 d . . . . .
C17 C -0.7027(10) -0.4349(7) -0.8817(4) 0.0169(12) Uani 1 1 d . . . . .
C18 C -0.5436(12) -0.3428(8) -0.9197(4) 0.0233(14) Uani 1 1 d . . . . .
H18 H -0.410313 -0.388476 -0.937895 0.028 Uiso 1 1 calc R U . . .
C19 C -0.5888(12) -0.1810(8) -0.9298(5) 0.0236(14) Uani 1 1 d . . . . .
H19 H -0.485004 -0.117733 -0.955630 0.028 Uiso 1 1 calc R U . . .
C20 C -0.7876(12) -0.1117(8) -0.9018(5) 0.0241(14) Uani 1 1 d . . . . .
H20 H -0.816635 -0.003576 -0.910154 0.029 Uiso 1 1 calc R U . . .
C21 C -0.9416(12) -0.2034(8) -0.8616(4) 0.0246(14) Uani 1 1 d . . . . .
H21 H -1.071540 -0.156717 -0.840995 0.029 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 C9 1.233(8) . ?
O2 C6 1.376(7) . ?
O2 C7 1.343(7) . ?
O3 C10 1.197(8) . ?
C1 C2 1.403(9) . ?
C1 C6 1.398(9) . ?
C1 C9 1.484(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.399(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(9) . ?
C7 C8 1.345(9) . ?
C7 C10 1.476(9) . ?
C8 C9 1.443(9) . ?
C8 C12 1.522(9) . ?
C10 C11 1.525(8) . ?
C11 H11 0.9800 . ?
C11 C12 1.570(8) . ?
C11 C15 1.555(8) . ?
C12 H12 0.9800 . ?
C12 C13 1.554(9) . ?
C13 H13 0.9800 . ?
C13 C14 1.558(9) . ?
C13 C17 1.520(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.541(9) . ?
C15 H15 0.9800 . ?
C15 C16 1.520(8) . ?
C16 C17 1.400(9) . ?
C16 C21 1.375(9) . ?
C17 C18 1.390(9) . ?
C18 H18 0.9300 . ?
C18 C19 1.388(9) . ?
C19 H19 0.9300 . ?
C19 C20 1.396(10) . ?
C20 H20 0.9300 . ?
C20 C21 1.384(9) . ?
C21 H21 0.9300 . ?

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
C7 O2 C6 115.7(5) . . ?
C2 C1 C9 121.0(6) . . ?
C6 C1 C2 117.9(6) . . ?
C6 C1 C9 121.0(6) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.7(6) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.1(6) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(6) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.8(6) . . ?
C6 C5 H5 120.6 . . ?
O2 C6 C1 122.3(5) . . ?
O2 C6 C5 115.6(6) . . ?
C5 C6 C1 122.0(6) . . ?
O2 C7 C8 127.3(6) . . ?
O2 C7 C10 119.9(5) . . ?
C8 C7 C10 112.8(5) . . ?
C7 C8 C9 120.8(6) . . ?
C7 C8 C12 111.3(5) . . ?
C9 C8 C12 127.8(6) . . ?
O1 C9 C1 122.4(6) . . ?
O1 C9 C8 125.1(6) . . ?
C8 C9 C1 112.5(5) . . ?
O3 C10 C7 127.1(6) . . ?
O3 C10 C11 126.7(6) . . ?
C7 C10 C11 106.1(5) . . ?
C10 C11 H11 111.2 . . ?
C10 C11 C12 106.0(5) . . ?
C10 C11 C15 114.5(5) . . ?
C12 C11 H11 111.2 . . ?
C15 C11 H11 111.2 . . ?
C15 C11 C12 102.3(5) . . ?
C8 C12 C11 103.7(5) . . ?
C8 C12 H12 111.5 . . ?
C8 C12 C13 114.7(5) . . ?
C11 C12 H12 111.5 . . ?
C13 C12 C11 103.3(5) . . ?
C13 C12 H12 111.5 . . ?
C12 C13 H13 116.2 . . ?
C12 C13 C14 101.0(5) . . ?
C14 C13 H13 116.2 . . ?
C17 C13 C12 104.6(5) . . ?
C17 C13 H13 116.2 . . ?
C17 C13 C14 100.2(5) . . ?
C13 C14 H14A 113.0 . . ?
C13 C14 H14B 113.0 . . ?
H14A C14 H14B 110.4 . . ?
C15 C14 C13 93.6(5) . . ?
C15 C14 H14A 113.0 . . ?
C15 C14 H14B 113.0 . . ?
C11 C15 H15 115.3 . . ?
C14 C15 C11 102.3(5) . . ?
C14 C15 H15 115.3 . . ?
C16 C15 C11 105.4(5) . . ?
C16 C15 C14 101.5(5) . . ?
C16 C15 H15 115.3 . . ?
C17 C16 C15 105.1(5) . . ?
C21 C16 C15 134.1(6) . . ?
C21 C16 C17 120.7(6) . . ?
C16 C17 C13 107.7(5) . . ?
C18 C17 C13 131.7(6) . . ?
C18 C17 C16 120.5(6) . . ?
C17 C18 H18 120.9 . . ?
C19 C18 C17 118.3(6) . . ?
C19 C18 H18 120.9 . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 121.0(6) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.2(6) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 C20 119.2(6) . . ?
C16 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?

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 C7 C8 C9 0.6(10) . . . . ?
O2 C7 C8 C12 -176.5(6) . . . . ?
O2 C7 C10 O3 1.1(10) . . . . ?
O2 C7 C10 C11 177.7(5) . . . . ?
O3 C10 C11 C12 175.8(6) . . . . ?
O3 C10 C11 C15 -72.2(8) . . . . ?
C1 C2 C3 C4 0.8(10) . . . . ?
C2 C1 C6 O2 178.7(6) . . . . ?
C2 C1 C6 C5 0.2(9) . . . . ?
C2 C1 C9 O1 5.5(10) . . . . ?
C2 C1 C9 C8 -173.3(6) . . . . ?
C2 C3 C4 C5 0.0(10) . . . . ?
C3 C4 C5 C6 -0.6(10) . . . . ?
C4 C5 C6 O2 -178.1(6) . . . . ?
C4 C5 C6 C1 0.5(10) . . . . ?
C6 O2 C7 C8 4.9(9) . . . . ?
C6 O2 C7 C10 -172.6(5) . . . . ?
C6 C1 C2 C3 -0.8(10) . . . . ?
C6 C1 C9 O1 -177.7(6) . . . . ?
C6 C1 C9 C8 3.5(9) . . . . ?
C7 O2 C6 C1 -5.9(8) . . . . ?
C7 O2 C6 C5 172.7(6) . . . . ?
C7 C8 C9 O1 176.5(7) . . . . ?
C7 C8 C9 C1 -4.6(9) . . . . ?
C7 C8 C12 C11 -1.5(7) . . . . ?
C7 C8 C12 C13 -113.4(6) . . . . ?
C7 C10 C11 C12 -0.8(6) . . . . ?
C7 C10 C11 C15 111.2(6) . . . . ?
C8 C7 C10 O3 -176.8(7) . . . . ?
C8 C7 C10 C11 -0.2(7) . . . . ?
C8 C12 C13 C14 75.7(6) . . . . ?
C8 C12 C13 C17 179.4(5) . . . . ?
C9 C1 C2 C3 176.1(6) . . . . ?
C9 C1 C6 O2 1.8(9) . . . . ?
C9 C1 C6 C5 -176.7(6) . . . . ?
C9 C8 C12 C11 -178.4(6) . . . . ?
C9 C8 C12 C13 69.7(8) . . . . ?
C10 C7 C8 C9 178.3(6) . . . . ?
C10 C7 C8 C12 1.1(8) . . . . ?
C10 C11 C12 C8 1.3(6) . . . . ?
C10 C11 C12 C13 121.3(5) . . . . ?
C10 C11 C15 C14 -78.9(6) . . . . ?
C10 C11 C15 C16 175.4(5) . . . . ?
C11 C12 C13 C14 -36.4(6) . . . . ?
C11 C12 C13 C17 67.3(6) . . . . ?
C11 C15 C16 C17 71.2(6) . . . . ?
C11 C15 C16 C21 -104.9(8) . . . . ?
C12 C8 C9 O1 -6.8(11) . . . . ?
C12 C8 C9 C1 172.0(6) . . . . ?
C12 C11 C15 C14 35.3(6) . . . . ?
C12 C11 C15 C16 -70.4(6) . . . . ?
C12 C13 C14 C15 56.6(5) . . . . ?
C12 C13 C17 C16 -71.7(6) . . . . ?
C12 C13 C17 C18 105.0(7) . . . . ?
C13 C14 C15 C11 -56.6(5) . . . . ?
C13 C14 C15 C16 52.2(5) . . . . ?
C13 C17 C18 C19 -178.0(6) . . . . ?
C14 C13 C17 C16 32.6(6) . . . . ?
C14 C13 C17 C18 -150.6(7) . . . . ?
C14 C15 C16 C17 -35.2(6) . . . . ?
C14 C15 C16 C21 148.8(7) . . . . ?
C15 C11 C12 C8 -119.0(5) . . . . ?
C15 C11 C12 C13 1.0(6) . . . . ?
C15 C16 C17 C13 1.2(6) . . . . ?
C15 C16 C17 C18 -176.0(6) . . . . ?
C15 C16 C21 C20 176.8(7) . . . . ?
C16 C17 C18 C19 -1.6(9) . . . . ?
C17 C13 C14 C15 -50.6(5) . . . . ?
C17 C16 C21 C20 1.2(10) . . . . ?
C17 C18 C19 C20 0.6(10) . . . . ?
C18 C19 C20 C21 1.3(10) . . . . ?
C19 C20 C21 C16 -2.1(10) . . . . ?
C21 C16 C17 C13 177.9(6) . . . . ?
C21 C16 C17 C18 0.7(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.435
_oxdiff_exptl_absorpt_empirical_full_min 0.761
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.572(7)
2 0.428(7)

####################################################################### 
# 
# 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_86-wit
_database_code_depnum_ccdc_archive 'CCDC 2056383'
loop_
_audit_author_name
_audit_author_address
'Han Wen-Yong'
;Zunyi Medical University
China
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;
_audit_creation_date             2020-09-30
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 O4'
_chemical_formula_sum            'C21 H20 O4'
_chemical_formula_weight         336.37
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.6748(14)
_cell_length_b                   13.565(3)
_cell_length_c                   10.788(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.16(3)
_cell_angle_gamma                90
_cell_volume                     814.8(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    939
_cell_measurement_temperature    100.01(11)
_cell_measurement_theta_max      27.5060
_cell_measurement_theta_min      2.9890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.1055
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_number            2283
_diffrn_reflns_point_group_measured_fraction_full 0.791
_diffrn_reflns_point_group_measured_fraction_max 0.795
_diffrn_reflns_theta_full        25.060
_diffrn_reflns_theta_max         25.060
_diffrn_reflns_theta_min         1.924
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  89.00   1.00    6.50    --   11.90  19.00-120.00  113
  2  ω     29.00  86.00   1.00    6.50    --   11.90  37.00  90.00   57
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0544346000
_diffrn_orient_matrix_UB_12      -0.0421268000
_diffrn_orient_matrix_UB_13      0.0325531000
_diffrn_orient_matrix_UB_21      -0.0411847000
_diffrn_orient_matrix_UB_22      0.0150222000
_diffrn_orient_matrix_UB_23      0.0550182000
_diffrn_orient_matrix_UB_31      -0.1075464000
_diffrn_orient_matrix_UB_32      -0.0271546000
_diffrn_orient_matrix_UB_33      -0.0200542000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.521
_reflns_Friedel_fraction_full    0.568
_reflns_Friedel_fraction_max     0.571
_reflns_number_gt                1832
_reflns_number_total             2283
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details 
;
 Flack x determined using 470 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.0(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2283
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0767
_refine_ls_restrained_S_all      1.184
_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)+(0.0964P)²+0.4549P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2175
_refine_ls_wR_factor_ref         0.2294
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.692(3)
 0.308(3)
2. 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
3. Uiso/Uaniso restraints and constraints
Uanis(C13) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
4.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C14(H14)
4.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B), C20(H20A,H20B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C18(H18)
4.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 -0.8357(6) -0.4936(3) -0.0064(3) 0.0286(10) Uani 1 1 d . . . . .
O2 O -0.8151(6) -0.3881(2) -0.3635(3) 0.0202(9) Uani 1 1 d . . . . .
O3 O -0.1389(6) -0.5836(3) -0.5086(3) 0.0263(9) Uani 1 1 d . . . . .
O4 O -0.2620(6) -0.4627(2) -0.6495(3) 0.0244(9) Uani 1 1 d . . . . .
C1 C -0.9874(8) -0.3831(3) -0.1730(4) 0.0163(12) Uani 1 1 d . . . . .
C2 C -1.1565(9) -0.3388(4) -0.1136(5) 0.0246(14) Uani 1 1 d . . . . .
H2 H -1.167817 -0.359472 -0.032783 0.029 Uiso 1 1 calc R U . . .
C3 C -1.3097(9) -0.2647(4) -0.1706(4) 0.0236(13) Uani 1 1 d . . . . .
H3 H -1.422575 -0.236586 -0.129266 0.028 Uiso 1 1 calc R U . . .
C4 C -1.2894(9) -0.2336(4) -0.2915(5) 0.0269(14) Uani 1 1 d . . . . .
H4 H -1.390442 -0.184298 -0.331270 0.032 Uiso 1 1 calc R U . . .
C5 C -1.1209(9) -0.2751(4) -0.3531(4) 0.0226(13) Uani 1 1 d . . . . .
H5 H -1.106639 -0.253434 -0.433107 0.027 Uiso 1 1 calc R U . . .
C6 C -0.9749(9) -0.3492(4) -0.2939(4) 0.0207(13) Uani 1 1 d . . . . .
C7 C -0.6740(8) -0.4638(4) -0.3071(4) 0.0186(13) Uani 1 1 d . . . . .
C8 C -0.6737(7) -0.5020(3) -0.1919(4) 0.0148(12) Uani 1 1 d . . . . .
C9 C -0.8307(9) -0.4635(4) -0.1125(4) 0.0198(12) Uani 1 1 d . . . . .
C10 C -0.4946(8) -0.5827(4) -0.1654(4) 0.0165(11) Uani 1 1 d . . . . .
H10 H -0.371617 -0.569019 -0.090213 0.020 Uiso 1 1 calc R U . . .
C11 C -0.3848(8) -0.5912(3) -0.2864(4) 0.0160(11) Uani 1 1 d . . . . .
H11 H -0.209900 -0.583505 -0.265871 0.019 Uiso 1 1 calc R U . . .
C12 C -0.4539(8) -0.6968(3) -0.3322(4) 0.0204(13) Uani 1 1 d . . . . .
H12 H -0.449298 -0.708777 -0.421309 0.024 Uiso 1 1 calc R U . . .
C13 C -0.7011(8) -0.7084(4) -0.2989(4) 0.0175(9) Uani 1 1 d . U . . .
H13A H -0.764525 -0.774727 -0.313300 0.021 Uiso 1 1 calc R U . . .
H13B H -0.816481 -0.660740 -0.341348 0.021 Uiso 1 1 calc R U . . .
C14 C -0.6130(8) -0.6850(3) -0.1577(4) 0.0181(12) Uani 1 1 d . . . . .
H14 H -0.737919 -0.686791 -0.106488 0.022 Uiso 1 1 calc R U . . .
C15 C -0.4093(8) -0.7607(4) -0.1198(4) 0.0198(12) Uani 1 1 d . . . . .
H15A H -0.290508 -0.737359 -0.048844 0.024 Uiso 1 1 calc R U . . .
H15B H -0.471300 -0.823774 -0.098420 0.024 Uiso 1 1 calc R U . . .
C16 C -0.3034(9) -0.7680(4) -0.2405(4) 0.0223(13) Uani 1 1 d . . . . .
H16A H -0.135611 -0.748759 -0.223933 0.027 Uiso 1 1 calc R U . . .
H16B H -0.317044 -0.834643 -0.273759 0.027 Uiso 1 1 calc R U . . .
C17 C -0.5002(8) -0.5081(4) -0.3725(4) 0.0187(12) Uani 1 1 d . . . . .
C18 C -0.4585(8) -0.4760(4) -0.4819(4) 0.0217(13) Uani 1 1 d . . . . .
H18 H -0.554181 -0.425231 -0.522051 0.026 Uiso 1 1 calc R U . . .
C19 C -0.2690(9) -0.5159(4) -0.5443(4) 0.0241(13) Uani 1 1 d . . . . .
C20 C -0.0960(8) -0.4976(4) -0.7279(4) 0.0220(13) Uani 1 1 d . . . . .
H20A H 0.047308 -0.523959 -0.674404 0.026 Uiso 1 1 calc R U . . .
H20B H -0.048627 -0.442925 -0.775610 0.026 Uiso 1 1 calc R U . . .
C21 C -0.2121(9) -0.5760(4) -0.8171(4) 0.0272(14) Uani 1 1 d . . . . .
H21A H -0.237101 -0.633885 -0.770159 0.041 Uiso 1 1 calc R U . . .
H21B H -0.109774 -0.591788 -0.875503 0.041 Uiso 1 1 calc R U . . .
H21C H -0.363797 -0.552470 -0.862815 0.041 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 C9 1.221(5) . ?
O2 C6 1.389(6) . ?
O2 C7 1.369(5) . ?
O3 C19 1.195(6) . ?
O4 C19 1.351(6) . ?
O4 C20 1.461(6) . ?
C1 C2 1.390(7) . ?
C1 C6 1.398(7) . ?
C1 C9 1.477(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.392(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.397(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(7) . ?
C7 C8 1.347(6) . ?
C7 C17 1.450(7) . ?
C8 C9 1.448(7) . ?
C8 C10 1.483(6) . ?
C10 H10 0.9800 . ?
C10 C11 1.556(7) . ?
C10 C14 1.551(7) . ?
C11 H11 0.9800 . ?
C11 C12 1.541(6) . ?
C11 C17 1.526(6) . ?
C12 H12 0.9800 . ?
C12 C13 1.522(7) . ?
C12 C16 1.521(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.542(6) . ?
C14 H14 0.9800 . ?
C14 C15 1.541(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.539(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.322(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.477(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.498(7) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C7 O2 C6 115.6(4) . . ?
C19 O4 C20 116.1(4) . . ?
C2 C1 C6 116.9(4) . . ?
C2 C1 C9 121.7(4) . . ?
C6 C1 C9 121.4(4) . . ?
C1 C2 H2 118.8 . . ?
C1 C2 C3 122.5(5) . . ?
C3 C2 H2 118.8 . . ?
C2 C3 H3 120.9 . . ?
C2 C3 C4 118.2(5) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.0(5) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.9(5) . . ?
C6 C5 H5 120.6 . . ?
O2 C6 C1 122.4(4) . . ?
C5 C6 O2 115.1(4) . . ?
C5 C6 C1 122.6(5) . . ?
O2 C7 C17 119.3(4) . . ?
C8 C7 O2 126.5(4) . . ?
C8 C7 C17 114.2(4) . . ?
C7 C8 C9 121.0(4) . . ?
C7 C8 C10 109.9(4) . . ?
C9 C8 C10 129.0(4) . . ?
O1 C9 C1 122.7(5) . . ?
O1 C9 C8 124.2(4) . . ?
C8 C9 C1 113.1(4) . . ?
C8 C10 H10 111.8 . . ?
C8 C10 C11 105.3(4) . . ?
C8 C10 C14 112.5(4) . . ?
C11 C10 H10 111.8 . . ?
C14 C10 H10 111.8 . . ?
C14 C10 C11 103.1(4) . . ?
C10 C11 H11 110.8 . . ?
C12 C11 C10 102.7(4) . . ?
C12 C11 H11 110.8 . . ?
C17 C11 C10 105.2(4) . . ?
C17 C11 H11 110.8 . . ?
C17 C11 C12 116.1(3) . . ?
C11 C12 H12 114.5 . . ?
C13 C12 C11 102.1(4) . . ?
C13 C12 H12 114.5 . . ?
C16 C12 C11 107.8(3) . . ?
C16 C12 H12 114.5 . . ?
C16 C12 C13 102.0(4) . . ?
C12 C13 H13A 112.9 . . ?
C12 C13 H13B 112.9 . . ?
C12 C13 C14 94.3(3) . . ?
H13A C13 H13B 110.3 . . ?
C14 C13 H13A 112.9 . . ?
C14 C13 H13B 112.9 . . ?
C10 C14 H14 114.9 . . ?
C13 C14 C10 101.1(4) . . ?
C13 C14 H14 114.9 . . ?
C15 C14 C10 107.5(4) . . ?
C15 C14 C13 102.0(4) . . ?
C15 C14 H14 114.9 . . ?
C14 C15 H15A 111.3 . . ?
C14 C15 H15B 111.3 . . ?
H15A C15 H15B 109.2 . . ?
C16 C15 C14 102.4(4) . . ?
C16 C15 H15A 111.3 . . ?
C16 C15 H15B 111.3 . . ?
C12 C16 C15 104.3(4) . . ?
C12 C16 H16A 110.9 . . ?
C12 C16 H16B 110.9 . . ?
C15 C16 H16A 110.9 . . ?
C15 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
C7 C17 C11 105.2(4) . . ?
C18 C17 C7 123.7(4) . . ?
C18 C17 C11 131.1(5) . . ?
C17 C18 H18 118.0 . . ?
C17 C18 C19 123.9(4) . . ?
C19 C18 H18 118.0 . . ?
O3 C19 O4 124.4(5) . . ?
O3 C19 C18 126.4(5) . . ?
O4 C19 C18 109.2(4) . . ?
O4 C20 H20A 109.6 . . ?
O4 C20 H20B 109.6 . . ?
O4 C20 C21 110.4(4) . . ?
H20A C20 H20B 108.1 . . ?
C21 C20 H20A 109.6 . . ?
C21 C20 H20B 109.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
O2 C7 C8 C9 -0.6(7) . . . . ?
O2 C7 C8 C10 -179.9(4) . . . . ?
O2 C7 C17 C11 -177.6(4) . . . . ?
O2 C7 C17 C18 4.1(7) . . . . ?
C1 C2 C3 C4 -0.6(7) . . . . ?
C2 C1 C6 O2 -179.3(4) . . . . ?
C2 C1 C6 C5 0.2(7) . . . . ?
C2 C1 C9 O1 -2.1(7) . . . . ?
C2 C1 C9 C8 177.8(4) . . . . ?
C2 C3 C4 C5 -0.2(7) . . . . ?
C3 C4 C5 C6 1.0(7) . . . . ?
C4 C5 C6 O2 178.6(4) . . . . ?
C4 C5 C6 C1 -1.0(7) . . . . ?
C6 O2 C7 C8 -1.0(6) . . . . ?
C6 O2 C7 C17 -179.3(4) . . . . ?
C6 C1 C2 C3 0.6(7) . . . . ?
C6 C1 C9 O1 179.0(4) . . . . ?
C6 C1 C9 C8 -1.1(6) . . . . ?
C7 O2 C6 C1 1.5(6) . . . . ?
C7 O2 C6 C5 -178.1(4) . . . . ?
C7 C8 C9 O1 -178.5(4) . . . . ?
C7 C8 C9 C1 1.6(6) . . . . ?
C7 C8 C10 C11 -1.5(5) . . . . ?
C7 C8 C10 C14 -113.1(4) . . . . ?
C7 C17 C18 C19 175.1(4) . . . . ?
C8 C7 C17 C11 3.9(5) . . . . ?
C8 C7 C17 C18 -174.4(4) . . . . ?
C8 C10 C11 C12 -118.1(4) . . . . ?
C8 C10 C11 C17 3.7(4) . . . . ?
C8 C10 C14 C13 77.8(4) . . . . ?
C8 C10 C14 C15 -175.7(4) . . . . ?
C9 C1 C2 C3 -178.3(4) . . . . ?
C9 C1 C6 O2 -0.4(7) . . . . ?
C9 C1 C6 C5 179.2(4) . . . . ?
C9 C8 C10 C11 179.3(4) . . . . ?
C9 C8 C10 C14 67.7(6) . . . . ?
C10 C8 C9 O1 0.6(8) . . . . ?
C10 C8 C9 C1 -179.3(4) . . . . ?
C10 C11 C12 C13 35.8(4) . . . . ?
C10 C11 C12 C16 -71.1(4) . . . . ?
C10 C11 C17 C7 -4.5(4) . . . . ?
C10 C11 C17 C18 173.6(5) . . . . ?
C10 C14 C15 C16 -71.5(4) . . . . ?
C11 C10 C14 C13 -35.1(4) . . . . ?
C11 C10 C14 C15 71.4(4) . . . . ?
C11 C12 C13 C14 -56.5(4) . . . . ?
C11 C12 C16 C15 71.7(5) . . . . ?
C11 C17 C18 C19 -2.7(8) . . . . ?
C12 C11 C17 C7 108.3(5) . . . . ?
C12 C11 C17 C18 -73.6(7) . . . . ?
C12 C13 C14 C10 55.9(4) . . . . ?
C12 C13 C14 C15 -54.8(4) . . . . ?
C13 C12 C16 C15 -35.4(4) . . . . ?
C13 C14 C15 C16 34.4(4) . . . . ?
C14 C10 C11 C12 -0.1(4) . . . . ?
C14 C10 C11 C17 121.8(4) . . . . ?
C14 C15 C16 C12 0.3(5) . . . . ?
C16 C12 C13 C14 54.9(4) . . . . ?
C17 C7 C8 C9 177.8(4) . . . . ?
C17 C7 C8 C10 -1.5(5) . . . . ?
C17 C11 C12 C13 -78.3(5) . . . . ?
C17 C11 C12 C16 174.7(4) . . . . ?
C17 C18 C19 O3 3.7(8) . . . . ?
C17 C18 C19 O4 -175.6(4) . . . . ?
C19 O4 C20 C21 85.0(5) . . . . ?
C20 O4 C19 O3 5.3(7) . . . . ?
C20 O4 C19 C18 -175.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.560
_oxdiff_exptl_absorpt_empirical_full_min 0.675
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.692(3)
2 0.308(3)

####################################################################### 
# 
# 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_iproh
_database_code_depnum_ccdc_archive 'CCDC 2056385'
loop_
_audit_author_name
_audit_author_address
'Han Wen-Yong'
;Zunyi Medical University
China
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;
_audit_creation_date             2021-01-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 O3'
_chemical_formula_sum            'C17 H16 O3'
_chemical_formula_weight         268.30
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8459(5)
_cell_length_b                   8.6461(6)
_cell_length_c                   11.8123(8)
_cell_angle_alpha                107.918(6)
_cell_angle_beta                 101.256(6)
_cell_angle_gamma                98.709(6)
_cell_volume                     635.49(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2395
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      29.1040
_cell_measurement_theta_min      2.5250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4187
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.542
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -37.00  59.00   1.00    1.00    --  -11.27  77.00 150.00   96
  2  ω    -16.00  87.00   1.00    1.00    --   11.90  77.00 -60.00  103
  3  ω    -11.00  74.00   1.00    1.00    --   11.90  77.00  60.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0667379000
_diffrn_orient_matrix_UB_12      -0.0233314000
_diffrn_orient_matrix_UB_13      -0.0595162000
_diffrn_orient_matrix_UB_21      -0.0852792000
_diffrn_orient_matrix_UB_22      -0.0133390000
_diffrn_orient_matrix_UB_23      0.0244143000
_diffrn_orient_matrix_UB_31      -0.0061532000
_diffrn_orient_matrix_UB_32      0.0843432000
_diffrn_orient_matrix_UB_33      0.0112374000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1934
_reflns_number_total             2228
_reflns_odcompleteness_completeness 99.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.075(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.054
_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)+(0.0468P)²+0.1408P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1000
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 -0.07471(14) -0.19201(14) -0.40339(9) 0.0260(3) Uani 1 1 d . . . . .
O2 O -0.70424(14) -0.30852(12) -0.48635(9) 0.0194(3) Uani 1 1 d . . . . .
O3 O -0.79080(15) -0.27440(14) -0.24250(9) 0.0264(3) Uani 1 1 d . . . . .
H3 H -0.879731 -0.260383 -0.293501 0.040 Uiso 1 1 calc R U . . .
C1 C -0.3921(2) -0.19826(17) -0.53114(13) 0.0173(3) Uani 1 1 d . . . . .
C2 C -0.3051(2) -0.12758(18) -0.60741(13) 0.0202(3) Uani 1 1 d . . . . .
H2 H -0.163643 -0.096302 -0.591390 0.024 Uiso 1 1 calc R U . . .
C3 C -0.4261(2) -0.10415(19) -0.70506(13) 0.0232(4) Uani 1 1 d . . . . .
H3A H -0.366766 -0.055683 -0.754043 0.028 Uiso 1 1 calc R U . . .
C4 C -0.6391(2) -0.15331(19) -0.73090(13) 0.0249(4) Uani 1 1 d . . . . .
H4 H -0.720477 -0.140068 -0.798597 0.030 Uiso 1 1 calc R U . . .
C5 C -0.7295(2) -0.22102(19) -0.65732(13) 0.0220(4) Uani 1 1 d . . . . .
H5 H -0.871095 -0.252154 -0.673958 0.026 Uiso 1 1 calc R U . . .
C6 C -0.6049(2) -0.24192(17) -0.55766(12) 0.0179(3) Uani 1 1 d . . . . .
C7 C -0.5850(2) -0.32851(18) -0.38870(12) 0.0169(3) Uani 1 1 d . . . . .
C8 C -0.3791(2) -0.29513(17) -0.35689(12) 0.0162(3) Uani 1 1 d . . . . .
C9 C -0.2638(2) -0.22622(18) -0.42677(12) 0.0175(3) Uani 1 1 d . . . . .
C10 C -0.3010(2) -0.34138(17) -0.24679(12) 0.0158(3) Uani 1 1 d . . . . .
H10 H -0.225404 -0.429283 -0.267738 0.019 Uiso 1 1 calc R U . . .
C11 C -0.5007(2) -0.40691(18) -0.21210(13) 0.0177(3) Uani 1 1 d . . . . .
H11 H -0.512198 -0.523865 -0.218588 0.021 Uiso 1 1 calc R U . . .
C12 C -0.6856(2) -0.39000(19) -0.30379(13) 0.0195(3) Uani 1 1 d . . . . .
H12 H -0.779306 -0.499118 -0.349230 0.023 Uiso 1 1 calc R U . . .
C13 C -0.4590(2) -0.29490(18) -0.07676(13) 0.0197(3) Uani 1 1 d . . . . .
H13 H -0.580771 -0.290388 -0.044970 0.024 Uiso 1 1 calc R U . . .
C14 C -0.2874(2) -0.3481(2) -0.00212(14) 0.0239(4) Uani 1 1 d . . . . .
H14A H -0.312002 -0.468698 -0.026505 0.029 Uiso 1 1 calc R U . . .
H14B H -0.275387 -0.300956 0.085483 0.029 Uiso 1 1 calc R U . . .
C15 C -0.0924(2) -0.2761(2) -0.03517(13) 0.0233(4) Uani 1 1 d . . . . .
H15A H 0.004800 -0.193254 0.036990 0.028 Uiso 1 1 calc R U . . .
H15B H -0.026618 -0.363770 -0.071596 0.028 Uiso 1 1 calc R U . . .
C16 C -0.1769(2) -0.19688(18) -0.12840(13) 0.0184(3) Uani 1 1 d . . . . .
H16 H -0.075096 -0.115013 -0.140587 0.022 Uiso 1 1 calc R U . . .
C17 C -0.3455(2) -0.12677(18) -0.07541(13) 0.0200(3) Uani 1 1 d . . . . .
H17A H -0.427234 -0.081684 -0.128721 0.024 Uiso 1 1 calc R U . . .
H17B H -0.293350 -0.044605 0.006951 0.024 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 C9 1.2385(16) . ?
O2 C6 1.3810(17) . ?
O2 C7 1.3509(17) . ?
O3 H3 0.8200 . ?
O3 C12 1.4207(17) . ?
C1 C2 1.406(2) . ?
C1 C6 1.395(2) . ?
C1 C9 1.475(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(2) . ?
C3 H3A 0.9300 . ?
C3 C4 1.399(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(2) . ?
C7 C8 1.347(2) . ?
C7 C12 1.500(2) . ?
C8 C9 1.440(2) . ?
C8 C10 1.5000(19) . ?
C10 H10 0.9800 . ?
C10 C11 1.5760(19) . ?
C10 C16 1.542(2) . ?
C11 H11 0.9800 . ?
C11 C12 1.5542(19) . ?
C11 C13 1.536(2) . ?
C12 H12 0.9800 . ?
C13 H13 0.9800 . ?
C13 C14 1.542(2) . ?
C13 C17 1.535(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.557(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.534(2) . ?
C16 H16 0.9800 . ?
C16 C17 1.5335(19) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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
C7 O2 C6 116.67(11) . . ?
C12 O3 H3 109.5 . . ?
C2 C1 C9 121.49(13) . . ?
C6 C1 C2 117.71(13) . . ?
C6 C1 C9 120.79(13) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 120.90(14) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3A 120.1 . . ?
C2 C3 C4 119.87(14) . . ?
C4 C3 H3A 120.1 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.80(14) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.66(14) . . ?
C6 C5 H5 120.7 . . ?
O2 C6 C1 121.93(13) . . ?
O2 C6 C5 116.04(13) . . ?
C5 C6 C1 122.03(14) . . ?
O2 C7 C12 118.64(12) . . ?
C8 C7 O2 126.25(13) . . ?
C8 C7 C12 115.10(13) . . ?
C7 C8 C9 120.55(13) . . ?
C7 C8 C10 110.94(12) . . ?
C9 C8 C10 128.51(12) . . ?
O1 C9 C1 121.82(13) . . ?
O1 C9 C8 124.43(13) . . ?
C8 C9 C1 113.75(12) . . ?
C8 C10 H10 110.7 . . ?
C8 C10 C11 104.05(10) . . ?
C8 C10 C16 116.55(12) . . ?
C11 C10 H10 110.7 . . ?
C16 C10 H10 110.7 . . ?
C16 C10 C11 103.63(10) . . ?
C10 C11 H11 110.2 . . ?
C12 C11 C10 107.34(11) . . ?
C12 C11 H11 110.2 . . ?
C13 C11 C10 101.96(11) . . ?
C13 C11 H11 110.2 . . ?
C13 C11 C12 116.50(11) . . ?
O3 C12 C7 111.63(12) . . ?
O3 C12 C11 111.48(11) . . ?
O3 C12 H12 110.4 . . ?
C7 C12 C11 102.35(11) . . ?
C7 C12 H12 110.4 . . ?
C11 C12 H12 110.4 . . ?
C11 C13 H13 114.7 . . ?
C11 C13 C14 107.04(11) . . ?
C14 C13 H13 114.7 . . ?
C17 C13 C11 102.62(11) . . ?
C17 C13 H13 114.7 . . ?
C17 C13 C14 101.60(11) . . ?
C13 C14 H14A 111.1 . . ?
C13 C14 H14B 111.1 . . ?
C13 C14 C15 103.37(11) . . ?
H14A C14 H14B 109.1 . . ?
C15 C14 H14A 111.1 . . ?
C15 C14 H14B 111.1 . . ?
C14 C15 H15A 111.2 . . ?
C14 C15 H15B 111.2 . . ?
H15A C15 H15B 109.1 . . ?
C16 C15 C14 102.98(11) . . ?
C16 C15 H15A 111.2 . . ?
C16 C15 H15B 111.2 . . ?
C10 C16 H16 114.9 . . ?
C15 C16 C10 106.85(12) . . ?
C15 C16 H16 114.9 . . ?
C17 C16 C10 102.27(11) . . ?
C17 C16 C15 101.35(11) . . ?
C17 C16 H16 114.9 . . ?
C13 C17 H17A 112.8 . . ?
C13 C17 H17B 112.8 . . ?
C16 C17 C13 94.80(11) . . ?
C16 C17 H17A 112.8 . . ?
C16 C17 H17B 112.8 . . ?
H17A C17 H17B 110.2 . . ?

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
O2 C7 C8 C9 2.2(2) . . . . ?
O2 C7 C8 C10 -177.04(12) . . . . ?
O2 C7 C12 O3 -64.40(16) . . . . ?
O2 C7 C12 C11 176.26(11) . . . . ?
C1 C2 C3 C4 -1.0(2) . . . . ?
C2 C1 C6 O2 -178.49(12) . . . . ?
C2 C1 C6 C5 1.5(2) . . . . ?
C2 C1 C9 O1 -1.5(2) . . . . ?
C2 C1 C9 C8 178.30(12) . . . . ?
C2 C3 C4 C5 1.8(2) . . . . ?
C3 C4 C5 C6 -0.9(2) . . . . ?
C4 C5 C6 O2 179.25(12) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
C6 O2 C7 C8 -2.5(2) . . . . ?
C6 O2 C7 C12 176.11(11) . . . . ?
C6 C1 C2 C3 -0.6(2) . . . . ?
C6 C1 C9 O1 178.27(13) . . . . ?
C6 C1 C9 C8 -1.90(19) . . . . ?
C7 O2 C6 C1 0.42(19) . . . . ?
C7 O2 C6 C5 -179.58(12) . . . . ?
C7 C8 C9 O1 179.92(13) . . . . ?
C7 C8 C9 C1 0.09(19) . . . . ?
C7 C8 C10 C11 -1.58(15) . . . . ?
C7 C8 C10 C16 -114.95(14) . . . . ?
C8 C7 C12 O3 114.32(14) . . . . ?
C8 C7 C12 C11 -5.02(16) . . . . ?
C8 C10 C11 C12 -1.49(14) . . . . ?
C8 C10 C11 C13 -124.45(11) . . . . ?
C8 C10 C16 C15 -173.12(11) . . . . ?
C8 C10 C16 C17 80.84(14) . . . . ?
C9 C1 C2 C3 179.19(13) . . . . ?
C9 C1 C6 O2 1.7(2) . . . . ?
C9 C1 C6 C5 -178.29(13) . . . . ?
C9 C8 C10 C11 179.27(13) . . . . ?
C9 C8 C10 C16 65.90(18) . . . . ?
C10 C8 C9 O1 -1.0(2) . . . . ?
C10 C8 C9 C1 179.17(13) . . . . ?
C10 C11 C12 O3 -115.83(12) . . . . ?
C10 C11 C12 C7 3.63(14) . . . . ?
C10 C11 C13 C14 -70.13(13) . . . . ?
C10 C11 C13 C17 36.38(13) . . . . ?
C10 C16 C17 C13 53.83(12) . . . . ?
C11 C10 C16 C15 73.27(13) . . . . ?
C11 C10 C16 C17 -32.77(13) . . . . ?
C11 C13 C14 C15 74.10(14) . . . . ?
C11 C13 C17 C16 -55.87(12) . . . . ?
C12 C7 C8 C9 -176.42(12) . . . . ?
C12 C7 C8 C10 4.35(18) . . . . ?
C12 C11 C13 C14 173.37(12) . . . . ?
C12 C11 C13 C17 -80.11(14) . . . . ?
C13 C11 C12 O3 -2.35(17) . . . . ?
C13 C11 C12 C7 117.10(13) . . . . ?
C13 C14 C15 C16 -2.22(15) . . . . ?
C14 C13 C17 C16 54.76(12) . . . . ?
C14 C15 C16 C10 -69.82(14) . . . . ?
C14 C15 C16 C17 36.87(14) . . . . ?
C15 C16 C17 C13 -56.43(12) . . . . ?
C16 C10 C11 C12 120.84(12) . . . . ?
C16 C10 C11 C13 -2.11(13) . . . . ?
C17 C13 C14 C15 -33.13(14) . . . . ?

_olex2_date_sample_data_collection 2021-01-02
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.171
_oxdiff_exptl_absorpt_empirical_full_min 0.571
####################################################################### 
# 
# 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_86-33-3
_database_code_depnum_ccdc_archive 'CCDC 2056368'
loop_
_audit_author_name
_audit_author_address
'Han Wen-Yong'
;Zunyi Medical University
China
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;
_audit_creation_date             2020-08-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 O3'
_chemical_formula_sum            'C22 H16 O3'
_chemical_formula_weight         328.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.1695(4)
_cell_length_b                   11.3093(6)
_cell_length_c                   16.4310(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.784(5)
_cell_angle_gamma                90
_cell_volume                     1516.28(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3031
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.7050
_cell_measurement_theta_min      4.7170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.765
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5466
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.779
_diffrn_reflns_theta_min         4.749
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      7.00  44.00   1.00    1.00    --   40.73 -99.00 -90.00   37
  2  ω     28.00  55.00   1.00    1.00    --   40.73-125.00-120.00   27
  3  ω     34.00 136.00   1.00    1.00    --  107.58 -30.00-180.00  102
  4  ω     78.00 162.00   1.00    1.00    --  107.58  61.00   0.00   84
  5  ω    114.00 141.00   1.00    1.00    --  107.58 125.00 -90.00   27
  6  ω    145.00 178.00   1.00    1.00    --  107.58 125.00-120.00   33
  7  ω     95.00 122.00   1.00    1.00    --  107.58 125.00-120.00   27
  8  ω     81.00 134.00   1.00    1.00    --  107.58  30.00  90.00   53
  9  ω     35.00 114.00   1.00    1.00    --  107.58 -45.00  60.00   79
 10  ω    -94.00  -2.00   1.00    1.00    --  -40.73 125.00 -60.00   92
 11  ω   -113.00 -23.00   1.00    1.00    --  -40.73 -57.00  30.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0855708000
_diffrn_orient_matrix_UB_12      -0.0018199000
_diffrn_orient_matrix_UB_13      0.0815305000
_diffrn_orient_matrix_UB_21      0.1346148000
_diffrn_orient_matrix_UB_22      0.0809807000
_diffrn_orient_matrix_UB_23      0.0379239000
_diffrn_orient_matrix_UB_31      -0.1011618000
_diffrn_orient_matrix_UB_32      0.1094439000
_diffrn_orient_matrix_UB_33      -0.0269430000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2627
_reflns_number_total             2957
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2957
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.040
_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)+(0.0897P)²+0.8476P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1477
_refine_ls_wR_factor_ref         0.1532
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C19(H19), C20(H20), C21(H21), C22(H22)
;
_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 0.74722(17) 0.32067(12) 0.44284(8) 0.0245(3) Uani 1 1 d . . . . .
O2 O 0.53019(15) 0.64141(11) 0.38408(7) 0.0186(3) Uani 1 1 d . . . . .
O3 O 0.32689(16) 0.62913(12) 0.23588(8) 0.0240(3) Uani 1 1 d . . . . .
C1 C 0.7135(2) 0.52494(16) 0.47346(11) 0.0172(4) Uani 1 1 d . . . . .
C2 C 0.8231(2) 0.52465(17) 0.54218(11) 0.0201(4) Uani 1 1 d . . . . .
H2 H 0.873046 0.454357 0.559085 0.024 Uiso 1 1 calc R U . . .
C3 C 0.8571(2) 0.62742(18) 0.58471(11) 0.0233(4) Uani 1 1 d . . . . .
H3 H 0.930875 0.626358 0.629633 0.028 Uiso 1 1 calc R U . . .
C4 C 0.7810(2) 0.73337(17) 0.56050(11) 0.0227(4) Uani 1 1 d . . . . .
H4 H 0.804525 0.802377 0.589553 0.027 Uiso 1 1 calc R U . . .
C5 C 0.6712(2) 0.73652(17) 0.49378(11) 0.0205(4) Uani 1 1 d . . . . .
H5 H 0.620247 0.806849 0.477708 0.025 Uiso 1 1 calc R U . . .
C6 C 0.6385(2) 0.63176(16) 0.45110(10) 0.0174(4) Uani 1 1 d . . . . .
C7 C 0.5046(2) 0.54189(16) 0.34041(10) 0.0170(4) Uani 1 1 d . . . . .
C8 C 0.5697(2) 0.43427(15) 0.35481(10) 0.0159(4) Uani 1 1 d . . . . .
C9 C 0.6830(2) 0.41577(16) 0.42543(11) 0.0174(4) Uani 1 1 d . . . . .
C10 C 0.5064(2) 0.34462(15) 0.29358(10) 0.0161(4) Uani 1 1 d . . . . .
H10 H 0.444408 0.283932 0.321474 0.019 Uiso 1 1 calc R U . . .
C11 C 0.3872(2) 0.41641(16) 0.23584(10) 0.0173(4) Uani 1 1 d . . . . .
H11 H 0.275678 0.385809 0.239970 0.021 Uiso 1 1 calc R U . . .
C12 C 0.3942(2) 0.54320(17) 0.26641(10) 0.0180(4) Uani 1 1 d . . . . .
C13 C 0.4380(2) 0.40545(16) 0.14676(10) 0.0176(4) Uani 1 1 d . . . . .
H13 H 0.366932 0.453380 0.110046 0.021 Uiso 1 1 calc R U . . .
C14 C 0.6149(2) 0.44283(15) 0.14317(10) 0.0166(4) Uani 1 1 d . . . . .
C15 C 0.7226(2) 0.37611(15) 0.19409(10) 0.0164(4) Uani 1 1 d . . . . .
C16 C 0.6377(2) 0.28373(15) 0.24249(10) 0.0166(4) Uani 1 1 d . . . . .
H16 H 0.716370 0.239357 0.277512 0.020 Uiso 1 1 calc R U . . .
C17 C 0.5419(2) 0.20077(16) 0.18281(11) 0.0192(4) Uani 1 1 d . . . . .
H17A H 0.477800 0.145421 0.213203 0.023 Uiso 1 1 calc R U . . .
H17B H 0.618278 0.155830 0.151636 0.023 Uiso 1 1 calc R U . . .
C18 C 0.4267(2) 0.27331(16) 0.12406(11) 0.0205(4) Uani 1 1 d . . . . .
H18A H 0.458071 0.262204 0.068401 0.025 Uiso 1 1 calc R U . . .
H18B H 0.314701 0.246060 0.127844 0.025 Uiso 1 1 calc R U . . .
C19 C 0.8896(2) 0.39763(16) 0.19468(11) 0.0194(4) Uani 1 1 d . . . . .
H19 H 0.961354 0.353429 0.228154 0.023 Uiso 1 1 calc R U . . .
C20 C 0.9495(2) 0.48581(16) 0.14489(12) 0.0220(4) Uani 1 1 d . . . . .
H20 H 1.061658 0.500109 0.145024 0.026 Uiso 1 1 calc R U . . .
C21 C 0.8432(2) 0.55221(16) 0.09525(12) 0.0221(4) Uani 1 1 d . . . . .
H21 H 0.884318 0.611191 0.062503 0.027 Uiso 1 1 calc R U . . .
C22 C 0.6751(2) 0.53144(16) 0.09393(11) 0.0200(4) Uani 1 1 d . . . . .
H22 H 0.603915 0.576222 0.060543 0.024 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 C9 1.224(2) . ?
O2 C6 1.383(2) . ?
O2 C7 1.346(2) . ?
O3 C12 1.213(2) . ?
C1 C2 1.407(2) . ?
C1 C6 1.396(3) . ?
C1 C9 1.480(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.399(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.396(3) . ?
C7 C8 1.345(2) . ?
C7 C12 1.478(2) . ?
C8 C9 1.464(2) . ?
C8 C10 1.502(2) . ?
C10 H10 0.9800 . ?
C10 C11 1.555(2) . ?
C10 C16 1.554(2) . ?
C11 H11 0.9800 . ?
C11 C12 1.520(3) . ?
C11 C13 1.546(2) . ?
C13 H13 0.9800 . ?
C13 C14 1.510(2) . ?
C13 C18 1.542(3) . ?
C14 C15 1.405(2) . ?
C14 C22 1.393(2) . ?
C15 C16 1.503(2) . ?
C15 C19 1.385(2) . ?
C16 H16 0.9800 . ?
C16 C17 1.542(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.550(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19 0.9300 . ?
C19 C20 1.394(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.384(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.392(3) . ?
C22 H22 0.9300 . ?

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
C7 O2 C6 115.83(14) . . ?
C2 C1 C9 120.67(16) . . ?
C6 C1 C2 117.87(17) . . ?
C6 C1 C9 121.44(16) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.68(18) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.17(17) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.65(17) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.51(18) . . ?
C6 C5 H5 120.7 . . ?
O2 C6 C1 122.24(16) . . ?
O2 C6 C5 115.62(16) . . ?
C1 C6 C5 122.12(17) . . ?
O2 C7 C12 120.21(15) . . ?
C8 C7 O2 127.82(16) . . ?
C8 C7 C12 111.97(16) . . ?
C7 C8 C9 119.89(16) . . ?
C7 C8 C10 111.89(15) . . ?
C9 C8 C10 128.18(16) . . ?
O1 C9 C1 123.32(16) . . ?
O1 C9 C8 123.92(17) . . ?
C8 C9 C1 112.76(15) . . ?
C8 C10 H10 109.2 . . ?
C8 C10 C11 103.95(14) . . ?
C8 C10 C16 115.91(14) . . ?
C11 C10 H10 109.2 . . ?
C16 C10 H10 109.2 . . ?
C16 C10 C11 109.26(13) . . ?
C10 C11 H11 109.3 . . ?
C12 C11 C10 106.19(14) . . ?
C12 C11 H11 109.3 . . ?
C12 C11 C13 112.41(14) . . ?
C13 C11 C10 110.30(14) . . ?
C13 C11 H11 109.3 . . ?
O3 C12 C7 126.46(17) . . ?
O3 C12 C11 127.62(16) . . ?
C7 C12 C11 105.89(14) . . ?
C11 C13 H13 111.1 . . ?
C14 C13 C11 108.42(14) . . ?
C14 C13 H13 111.1 . . ?
C14 C13 C18 107.95(14) . . ?
C18 C13 C11 106.92(14) . . ?
C18 C13 H13 111.1 . . ?
C15 C14 C13 113.57(15) . . ?
C22 C14 C13 126.17(16) . . ?
C22 C14 C15 120.23(16) . . ?
C14 C15 C16 113.34(15) . . ?
C19 C15 C14 119.89(16) . . ?
C19 C15 C16 126.75(16) . . ?
C10 C16 H16 111.1 . . ?
C15 C16 C10 109.04(14) . . ?
C15 C16 H16 111.1 . . ?
C15 C16 C17 108.63(14) . . ?
C17 C16 C10 105.72(13) . . ?
C17 C16 H16 111.1 . . ?
C16 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
C16 C17 C18 110.36(14) . . ?
H17A C17 H17B 108.1 . . ?
C18 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
C13 C18 C17 109.56(14) . . ?
C13 C18 H18A 109.8 . . ?
C13 C18 H18B 109.8 . . ?
C17 C18 H18A 109.8 . . ?
C17 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?
C15 C19 H19 120.1 . . ?
C15 C19 C20 119.72(17) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.37(17) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.54(17) . . ?
C22 C21 H21 119.7 . . ?
C14 C22 H22 120.4 . . ?
C21 C22 C14 119.24(17) . . ?
C21 C22 H22 120.4 . . ?

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 C7 C8 C9 0.1(3) . . . . ?
O2 C7 C8 C10 178.08(16) . . . . ?
O2 C7 C12 O3 4.6(3) . . . . ?
O2 C7 C12 C11 -177.04(15) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C1 C6 O2 179.36(15) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C2 C1 C9 O1 1.3(3) . . . . ?
C2 C1 C9 C8 -178.13(15) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 O2 -178.73(14) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C6 O2 C7 C8 1.0(2) . . . . ?
C6 O2 C7 C12 -178.50(14) . . . . ?
C6 C1 C2 C3 -1.3(3) . . . . ?
C6 C1 C9 O1 179.56(16) . . . . ?
C6 C1 C9 C8 0.1(2) . . . . ?
C7 O2 C6 C1 -1.6(2) . . . . ?
C7 O2 C6 C5 176.83(15) . . . . ?
C7 C8 C9 O1 179.87(17) . . . . ?
C7 C8 C9 C1 -0.7(2) . . . . ?
C7 C8 C10 C11 0.34(18) . . . . ?
C7 C8 C10 C16 120.24(16) . . . . ?
C8 C7 C12 O3 -175.02(17) . . . . ?
C8 C7 C12 C11 3.35(19) . . . . ?
C8 C10 C11 C12 1.68(17) . . . . ?
C8 C10 C11 C13 123.73(15) . . . . ?
C8 C10 C16 C15 -61.17(19) . . . . ?
C8 C10 C16 C17 -177.81(14) . . . . ?
C9 C1 C2 C3 177.01(16) . . . . ?
C9 C1 C6 O2 1.1(3) . . . . ?
C9 C1 C6 C5 -177.27(15) . . . . ?
C9 C8 C10 C11 178.08(15) . . . . ?
C9 C8 C10 C16 -62.0(2) . . . . ?
C10 C8 C9 O1 2.3(3) . . . . ?
C10 C8 C9 C1 -178.27(15) . . . . ?
C10 C11 C12 O3 175.39(17) . . . . ?
C10 C11 C12 C7 -2.95(17) . . . . ?
C10 C11 C13 C14 -54.87(18) . . . . ?
C10 C11 C13 C18 61.29(17) . . . . ?
C10 C16 C17 C18 63.23(17) . . . . ?
C11 C10 C16 C15 55.80(18) . . . . ?
C11 C10 C16 C17 -60.83(17) . . . . ?
C11 C13 C14 C15 58.21(19) . . . . ?
C11 C13 C14 C22 -123.68(18) . . . . ?
C11 C13 C18 C17 -59.17(18) . . . . ?
C12 C7 C8 C9 179.70(14) . . . . ?
C12 C7 C8 C10 -2.3(2) . . . . ?
C12 C11 C13 C14 63.44(18) . . . . ?
C12 C11 C13 C18 179.59(14) . . . . ?
C13 C11 C12 O3 54.7(2) . . . . ?
C13 C11 C12 C7 -123.65(15) . . . . ?
C13 C14 C15 C16 -1.3(2) . . . . ?
C13 C14 C15 C19 177.53(15) . . . . ?
C13 C14 C22 C21 -177.40(16) . . . . ?
C14 C13 C18 C17 57.29(18) . . . . ?
C14 C15 C16 C10 -56.87(19) . . . . ?
C14 C15 C16 C17 57.90(19) . . . . ?
C14 C15 C19 C20 0.3(3) . . . . ?
C15 C14 C22 C21 0.6(3) . . . . ?
C15 C16 C17 C18 -53.68(18) . . . . ?
C15 C19 C20 C21 0.3(3) . . . . ?
C16 C10 C11 C12 -122.64(15) . . . . ?
C16 C10 C11 C13 -0.59(19) . . . . ?
C16 C15 C19 C20 178.89(16) . . . . ?
C16 C17 C18 C13 -2.80(19) . . . . ?
C18 C13 C14 C15 -57.28(19) . . . . ?
C18 C13 C14 C22 120.84(18) . . . . ?
C19 C15 C16 C10 124.42(18) . . . . ?
C19 C15 C16 C17 -120.82(18) . . . . ?
C19 C20 C21 C22 -0.4(3) . . . . ?
C20 C21 C22 C14 0.0(3) . . . . ?
C22 C14 C15 C16 -179.52(15) . . . . ?
C22 C14 C15 C19 -0.7(2) . . . . ?

_olex2_date_sample_data_collection 2020-08-18
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.987
_oxdiff_exptl_absorpt_empirical_full_min 0.634
####################################################################### 
# 
# 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_lsr
_database_code_depnum_ccdc_archive 'CCDC 2058395'
loop_
_audit_author_name
_audit_author_address
'Han Wen-Yong'
;Zunyi Medical University
China
;
_audit_update_record             
;
2021-01-25 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;
_audit_creation_date             2021-01-23
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 O2 S'
_chemical_formula_sum            'C17 H14 O2 S'
_chemical_formula_weight         282.34
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.3198(8)
_cell_length_b                   9.2495(7)
_cell_length_c                   21.0527(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2593.7(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3213
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.9090
_cell_measurement_theta_min      2.4690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7667
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         2.466
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  36.00   1.00    4.50    --   11.90 -38.00 150.00   89
  2  ω    -64.00 -12.00   1.00    4.50    --   11.90 -77.00 120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0346289000
_diffrn_orient_matrix_UB_12      -0.0270112000
_diffrn_orient_matrix_UB_13      0.0226544000
_diffrn_orient_matrix_UB_21      0.0378359000
_diffrn_orient_matrix_UB_22      -0.0023467000
_diffrn_orient_matrix_UB_23      -0.0237095000
_diffrn_orient_matrix_UB_31      0.0143205000
_diffrn_orient_matrix_UB_32      0.0717806000
_diffrn_orient_matrix_UB_33      0.0076594000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1936
_reflns_number_total             2282
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.049
_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)+(0.0350P)²+0.9101P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0840
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
;
_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 0.09404(3) 0.77046(5) 0.61355(2) 0.02711(16) Uani 1 1 d . . . . .
O1 O 0.40361(8) 0.63431(13) 0.54587(5) 0.0241(3) Uani 1 1 d . . . . .
O2 O 0.55907(9) 0.77335(15) 0.62004(6) 0.0330(3) Uani 1 1 d . . . . .
C1 C 0.22191(12) 0.61065(19) 0.53751(7) 0.0210(4) Uani 1 1 d . . . . .
C2 C 0.14257(12) 0.5438(2) 0.50474(8) 0.0253(4) Uani 1 1 d . . . . .
H2 H 0.076769 0.566280 0.515741 0.030 Uiso 1 1 calc R U . . .
C3 C 0.15988(13) 0.4465(2) 0.45697(8) 0.0290(4) Uani 1 1 d . . . . .
H3 H 0.106165 0.403108 0.436153 0.035 Uiso 1 1 calc R U . . .
C4 C 0.25806(13) 0.4124(2) 0.43955(8) 0.0288(4) Uani 1 1 d . . . . .
H4 H 0.269570 0.345728 0.407305 0.035 Uiso 1 1 calc R U . . .
C5 C 0.33775(13) 0.4766(2) 0.46963(8) 0.0260(4) Uani 1 1 d . . . . .
H5 H 0.403253 0.454685 0.457734 0.031 Uiso 1 1 calc R U . . .
C6 C 0.31919(12) 0.57439(19) 0.51800(8) 0.0215(4) Uani 1 1 d . . . . .
C7 C 0.38675(12) 0.72403(19) 0.59498(8) 0.0218(4) Uani 1 1 d . . . . .
C8 C 0.29650(12) 0.76241(19) 0.61856(8) 0.0205(4) Uani 1 1 d . . . . .
C9 C 0.20542(12) 0.71267(19) 0.58950(8) 0.0209(4) Uani 1 1 d . . . . .
C10 C 0.30811(11) 0.86007(19) 0.67487(8) 0.0204(4) Uani 1 1 d . . . . .
H10 H 0.269846 0.949775 0.669642 0.025 Uiso 1 1 calc R U . . .
C11 C 0.42331(11) 0.8898(2) 0.67884(8) 0.0225(4) Uani 1 1 d . . . . .
H11 H 0.438793 0.991989 0.671338 0.027 Uiso 1 1 calc R U . . .
C12 C 0.47066(13) 0.79387(19) 0.62934(8) 0.0237(4) Uani 1 1 d . . . . .
C13 C 0.45014(12) 0.84380(19) 0.74697(8) 0.0235(4) Uani 1 1 d . . . . .
H13 H 0.521958 0.828298 0.754462 0.028 Uiso 1 1 calc R U . . .
C14 C 0.38491(12) 0.70843(19) 0.75451(8) 0.0228(4) Uani 1 1 d . . . . .
H14A H 0.386983 0.668919 0.797172 0.027 Uiso 1 1 calc R U . . .
H14B H 0.400757 0.633951 0.723661 0.027 Uiso 1 1 calc R U . . .
C15 C 0.28576(12) 0.78686(19) 0.73987(8) 0.0205(4) Uani 1 1 d . . . . .
H15 H 0.225969 0.725137 0.740474 0.025 Uiso 1 1 calc R U . . .
C16 C 0.28744(12) 0.9056(2) 0.79061(8) 0.0250(4) Uani 1 1 d . . . . .
H16A H 0.264823 0.868939 0.831338 0.030 Uiso 1 1 calc R U . . .
H16B H 0.245578 0.986771 0.778360 0.030 Uiso 1 1 calc R U . . .
C17 C 0.39995(12) 0.9496(2) 0.79312(8) 0.0285(4) Uani 1 1 d . . . . .
H17A H 0.409179 1.048784 0.779380 0.034 Uiso 1 1 calc R U . . .
H17B H 0.426762 0.938787 0.835700 0.034 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
S1 C9 1.6563(16) . ?
O1 C6 1.3841(19) . ?
O1 C7 1.345(2) . ?
O2 C12 1.209(2) . ?
C1 C2 1.405(2) . ?
C1 C6 1.400(2) . ?
C1 C9 1.462(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.369(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.394(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.371(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(2) . ?
C7 C8 1.348(2) . ?
C7 C12 1.480(2) . ?
C8 C9 1.435(2) . ?
C8 C10 1.498(2) . ?
C10 H10 0.9800 . ?
C10 C11 1.561(2) . ?
C10 C15 1.556(2) . ?
C11 H11 0.9800 . ?
C11 C12 1.507(2) . ?
C11 C13 1.538(2) . ?
C13 H13 0.9800 . ?
C13 C14 1.532(3) . ?
C13 C17 1.532(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.538(2) . ?
C15 H15 0.9800 . ?
C15 C16 1.532(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.554(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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
C7 O1 C6 115.94(12) . . ?
C2 C1 C9 122.58(15) . . ?
C6 C1 C2 116.53(15) . . ?
C6 C1 C9 120.89(15) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.54(16) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.98(16) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.46(17) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 118.97(16) . . ?
C6 C5 H5 120.5 . . ?
O1 C6 C1 122.11(15) . . ?
O1 C6 C5 115.37(14) . . ?
C5 C6 C1 122.52(15) . . ?
O1 C7 C8 126.49(16) . . ?
O1 C7 C12 121.27(14) . . ?
C8 C7 C12 112.23(15) . . ?
C7 C8 C9 120.83(16) . . ?
C7 C8 C10 110.99(15) . . ?
C9 C8 C10 128.17(15) . . ?
C1 C9 S1 124.88(12) . . ?
C8 C9 S1 121.57(13) . . ?
C8 C9 C1 113.54(14) . . ?
C8 C10 H10 111.6 . . ?
C8 C10 C11 104.48(13) . . ?
C8 C10 C15 114.45(14) . . ?
C11 C10 H10 111.6 . . ?
C15 C10 H10 111.6 . . ?
C15 C10 C11 102.58(12) . . ?
C10 C11 H11 111.6 . . ?
C12 C11 C10 105.69(14) . . ?
C12 C11 H11 111.6 . . ?
C12 C11 C13 112.61(14) . . ?
C13 C11 C10 103.27(13) . . ?
C13 C11 H11 111.6 . . ?
O2 C12 C7 126.02(17) . . ?
O2 C12 C11 127.75(16) . . ?
C7 C12 C11 106.20(13) . . ?
C11 C13 H13 114.7 . . ?
C14 C13 C11 101.01(13) . . ?
C14 C13 H13 114.7 . . ?
C14 C13 C17 102.05(14) . . ?
C17 C13 C11 108.25(14) . . ?
C17 C13 H13 114.7 . . ?
C13 C14 H14A 112.8 . . ?
C13 C14 H14B 112.8 . . ?
C13 C14 C15 94.63(13) . . ?
H14A C14 H14B 110.3 . . ?
C15 C14 H14A 112.8 . . ?
C15 C14 H14B 112.8 . . ?
C10 C15 H15 114.9 . . ?
C14 C15 C10 102.55(13) . . ?
C14 C15 H15 114.9 . . ?
C16 C15 C10 107.37(14) . . ?
C16 C15 C14 100.71(13) . . ?
C16 C15 H15 114.9 . . ?
C15 C16 H16A 111.2 . . ?
C15 C16 H16B 111.2 . . ?
C15 C16 C17 103.02(13) . . ?
H16A C16 H16B 109.1 . . ?
C17 C16 H16A 111.2 . . ?
C17 C16 H16B 111.2 . . ?
C13 C17 C16 103.42(14) . . ?
C13 C17 H17A 111.1 . . ?
C13 C17 H17B 111.1 . . ?
C16 C17 H17A 111.1 . . ?
C16 C17 H17B 111.1 . . ?
H17A C17 H17B 109.0 . . ?

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 C7 C8 C9 -3.1(3) . . . . ?
O1 C7 C8 C10 177.94(15) . . . . ?
O1 C7 C12 O2 -4.1(3) . . . . ?
O1 C7 C12 C11 177.80(14) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C1 C6 O1 179.08(15) . . . . ?
C2 C1 C6 C5 -0.9(2) . . . . ?
C2 C1 C9 S1 -4.0(2) . . . . ?
C2 C1 C9 C8 176.93(15) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C4 C5 C6 O1 -179.96(15) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C6 O1 C7 C8 -1.2(2) . . . . ?
C6 O1 C7 C12 179.32(15) . . . . ?
C6 C1 C2 C3 1.1(2) . . . . ?
C6 C1 C9 S1 176.20(13) . . . . ?
C6 C1 C9 C8 -2.9(2) . . . . ?
C7 O1 C6 C1 3.2(2) . . . . ?
C7 O1 C6 C5 -176.84(14) . . . . ?
C7 C8 C9 S1 -174.28(14) . . . . ?
C7 C8 C9 C1 4.9(2) . . . . ?
C7 C8 C10 C11 5.55(19) . . . . ?
C7 C8 C10 C15 -105.83(17) . . . . ?
C8 C7 C12 O2 176.31(17) . . . . ?
C8 C7 C12 C11 -1.8(2) . . . . ?
C8 C10 C11 C12 -6.31(17) . . . . ?
C8 C10 C11 C13 -124.77(14) . . . . ?
C8 C10 C15 C14 81.77(16) . . . . ?
C8 C10 C15 C16 -172.61(13) . . . . ?
C9 C1 C2 C3 -178.74(16) . . . . ?
C9 C1 C6 O1 -1.1(2) . . . . ?
C9 C1 C6 C5 178.97(15) . . . . ?
C9 C8 C10 C11 -173.36(16) . . . . ?
C9 C8 C10 C15 75.3(2) . . . . ?
C10 C8 C9 S1 4.5(2) . . . . ?
C10 C8 C9 C1 -176.34(15) . . . . ?
C10 C11 C12 O2 -173.01(18) . . . . ?
C10 C11 C12 C7 5.02(17) . . . . ?
C10 C11 C13 C14 39.26(16) . . . . ?
C10 C11 C13 C17 -67.47(17) . . . . ?
C10 C15 C16 C17 -68.83(16) . . . . ?
C11 C10 C15 C14 -30.74(16) . . . . ?
C11 C10 C15 C16 74.88(15) . . . . ?
C11 C13 C14 C15 -57.04(14) . . . . ?
C11 C13 C17 C16 73.90(17) . . . . ?
C12 C7 C8 C9 176.47(15) . . . . ?
C12 C7 C8 C10 -2.5(2) . . . . ?
C12 C11 C13 C14 -74.27(16) . . . . ?
C12 C11 C13 C17 178.99(14) . . . . ?
C13 C11 C12 O2 -61.0(2) . . . . ?
C13 C11 C12 C7 117.06(15) . . . . ?
C13 C14 C15 C10 53.93(14) . . . . ?
C13 C14 C15 C16 -56.76(14) . . . . ?
C14 C13 C17 C16 -32.12(16) . . . . ?
C14 C15 C16 C17 38.08(16) . . . . ?
C15 C10 C11 C12 113.40(14) . . . . ?
C15 C10 C11 C13 -5.06(17) . . . . ?
C15 C16 C17 C13 -3.75(17) . . . . ?
C17 C13 C14 C15 54.53(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.323
_oxdiff_exptl_absorpt_empirical_full_min 0.469
