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

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

data_33
_database_code_depnum_ccdc_archive 'CCDC 1936540'
loop_
_audit_author_name
_audit_author_address
'Yijun Shi'
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2019-06-26 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;
_audit_creation_date             2018-09-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 O4'
_chemical_formula_sum            'C22 H18 O4'
_chemical_formula_weight         346.36
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N O'
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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   13.1979(16)
_cell_length_b                   11.4803(10)
_cell_length_c                   10.3400(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1566.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    893
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      25.7940
_cell_measurement_theta_min      4.0460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_unetI/netI     0.1124
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4836
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.733
_diffrn_reflns_theta_min         3.549
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3376
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_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  50.00   1.00   20.00    --   10.20  77.00   0.00   45
  2  ω    -11.00  66.00   1.00   20.00    --   10.20  77.00-150.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0280322000
_diffrn_orient_matrix_UB_12      -0.0211262000
_diffrn_orient_matrix_UB_13      0.0535878000
_diffrn_orient_matrix_UB_21      -0.0388061000
_diffrn_orient_matrix_UB_22      -0.0191810000
_diffrn_orient_matrix_UB_23      -0.0424427000
_diffrn_orient_matrix_UB_31      0.0243957000
_diffrn_orient_matrix_UB_32      -0.0548024000
_diffrn_orient_matrix_UB_33      -0.0058879000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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         0.892
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                1724
_reflns_number_total             2769
_reflns_odcompleteness_completeness 99.02
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.67
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2769
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1202
_refine_ls_R_factor_gt           0.0648
_refine_ls_restrained_S_all      1.038
_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)+(0.0302P)²+0.0296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1316
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_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:
 C5(H5), C7(H7), C12(H12), C13(H13), C16(H16), C22(H22), C10(H10), C6(H6),
 C2(H2), C8(H8), C15(H15), C3(H3), C18(H18), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b), C4(H4a,H4b)
;
_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
O2 O 0.6428(3) 0.4143(3) 0.7326(4) 0.0397(11) Uani 1 1 d . . . . .
O4 O 0.4505(3) 0.2929(3) 0.5984(4) 0.0421(11) Uani 1 1 d . . . . .
O3 O 0.4526(4) 0.1591(3) 0.2675(4) 0.0550(13) Uani 1 1 d . . . . .
O1 O 0.8508(4) 0.5636(4) 0.5512(5) 0.0602(14) Uani 1 1 d . . . . .
C21 C 0.5242(5) 0.2412(5) 0.5585(5) 0.0317(14) Uani 1 1 d . . . . .
C11 C 0.6244(4) 0.4687(5) 0.6345(5) 0.0303(14) Uani 1 1 d . . . . .
C19 C 0.6143(4) 0.2930(5) 0.4871(5) 0.0286(14) Uani 1 1 d . . . . .
C5 C 0.5098(5) 0.5983(5) 0.5244(5) 0.0355(15) Uani 1 1 d . . . . .
H5 H 0.442031 0.587572 0.561320 0.043 Uiso 1 1 calc R . . . .
C7 C 0.5442(5) 0.5036(5) 0.4286(5) 0.0345(15) Uani 1 1 d . . . . .
H7 H 0.491195 0.465399 0.377625 0.041 Uiso 1 1 calc R . . . .
C9 C 0.6226(4) 0.4230(5) 0.4968(5) 0.0274(13) Uani 1 1 d . . . . .
C12 C 0.7033(5) 0.2135(5) 0.5266(5) 0.0346(14) Uani 1 1 d . . . . .
H12 H 0.765536 0.251571 0.556356 0.041 Uiso 1 1 calc R . . . .
C13 C 0.6609(5) 0.1139(5) 0.6108(6) 0.0397(15) Uani 1 1 d . . . . .
H13 H 0.674658 0.120526 0.703682 0.048 Uiso 1 1 calc R . . . .
C16 C 0.5517(5) 0.0560(5) 0.4317(5) 0.0340(15) Uani 1 1 d . . . . .
H16 H 0.509017 -0.013330 0.422293 0.041 Uiso 1 1 calc R . . . .
C22 C 0.5483(5) 0.1130(5) 0.5730(5) 0.0350(14) Uani 1 1 d . . . . .
H22 H 0.504499 0.071780 0.634359 0.042 Uiso 1 1 calc R . . . .
C10 C 0.7118(5) 0.4861(5) 0.4192(5) 0.0343(15) Uani 1 1 d . . . . .
H10 H 0.754742 0.437635 0.363702 0.041 Uiso 1 1 calc R . . . .
C6 C 0.5983(4) 0.5979(4) 0.6228(6) 0.0332(14) Uani 1 1 d . . . . .
H6 H 0.581933 0.635312 0.705434 0.040 Uiso 1 1 calc R . . . .
C2 C 0.6864(5) 0.6598(4) 0.5457(6) 0.0381(15) Uani 1 1 d . . . . .
H2 H 0.714430 0.728160 0.589691 0.046 Uiso 1 1 calc R . . . .
C8 C 0.6309(5) 0.5638(5) 0.3523(5) 0.0387(16) Uani 1 1 d . . . . .
H8 H 0.627338 0.559882 0.257690 0.046 Uiso 1 1 calc R . . . .
C15 C 0.6642(5) 0.0331(5) 0.4112(6) 0.0432(17) Uani 1 1 d . . . . .
H15 H 0.680895 -0.023504 0.343515 0.052 Uiso 1 1 calc R . . . .
C1 C 0.7642(5) 0.5697(5) 0.5109(6) 0.0391(15) Uani 1 1 d . . . . .
C14 C 0.7043(5) 0.0049(5) 0.5452(6) 0.0493(18) Uani 1 1 d . . . . .
H14A H 0.777760 0.002316 0.548166 0.059 Uiso 1 1 calc R . . . .
H14B H 0.676240 -0.066621 0.579795 0.059 Uiso 1 1 calc R . . . .
C3 C 0.6358(5) 0.6877(5) 0.4139(6) 0.0389(15) Uani 1 1 d . . . . .
H3 H 0.669287 0.747689 0.361781 0.047 Uiso 1 1 calc R . . . .
C17 C 0.5280(6) 0.1514(5) 0.3358(6) 0.0398(17) Uani 1 1 d . . . . .
C18 C 0.6154(5) 0.2369(5) 0.3459(6) 0.0375(16) Uani 1 1 d . . . . .
H18 H 0.626737 0.289404 0.272548 0.045 Uiso 1 1 calc R . . . .
C4 C 0.5257(5) 0.7115(5) 0.4492(6) 0.0434(17) Uani 1 1 d . . . . .
H4A H 0.482227 0.717223 0.373848 0.052 Uiso 1 1 calc R . . . .
H4B H 0.517957 0.780150 0.503030 0.052 Uiso 1 1 calc R . . . .
C20 C 0.7046(5) 0.1590(5) 0.3888(6) 0.0421(17) Uani 1 1 d . . . . .
H20 H 0.767800 0.166509 0.339607 0.050 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C11 1.216(6) . ?
O4 C21 1.212(6) . ?
O3 C17 1.223(7) . ?
O1 C1 1.219(7) . ?
C21 C19 1.521(8) . ?
C21 C22 1.513(7) . ?
C11 C9 1.517(7) . ?
C11 C6 1.528(7) . ?
C19 C9 1.500(7) . ?
C19 C12 1.543(8) . ?
C19 C18 1.596(7) . ?
C5 C7 1.539(8) . ?
C5 C6 1.549(8) . ?
C5 C4 1.529(8) . ?
C7 C9 1.558(8) . ?
C7 C8 1.553(8) . ?
C9 C10 1.598(8) . ?
C12 C13 1.543(8) . ?
C12 C20 1.556(8) . ?
C13 C22 1.537(8) . ?
C13 C14 1.534(8) . ?
C16 C22 1.602(7) . ?
C16 C15 1.524(9) . ?
C16 C17 1.509(8) . ?
C10 C8 1.554(8) . ?
C10 C1 1.516(8) . ?
C6 C2 1.578(8) . ?
C2 C1 1.501(8) . ?
C2 C3 1.551(8) . ?
C8 C3 1.560(8) . ?
C15 C14 1.518(8) . ?
C15 C20 1.558(8) . ?
C3 C4 1.523(9) . ?
C17 C18 1.518(9) . ?
C18 C20 1.544(8) . ?

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
O4 C21 C19 126.9(5) . . ?
O4 C21 C22 127.7(5) . . ?
C22 C21 C19 105.3(5) . . ?
O2 C11 C00A 127.5(5) . . ?
O2 C11 C6 127.6(5) . . ?
C9 C11 C6 104.9(5) . . ?
C21 C19 C12 103.6(4) . . ?
C21 C19 C18 107.0(5) . . ?
C9 C19 C21 114.5(4) . . ?
C9 C19 C12 121.0(5) . . ?
C9 C19 C18 117.5(4) . . ?
C12 C19 C18 89.8(4) . . ?
C7 C5 C6 101.4(4) . . ?
C4 C5 C7 103.5(5) . . ?
C4 C5 C6 103.5(5) . . ?
C5 C7 C9 109.0(4) . . ?
C5 C7 C8 103.3(5) . . ?
C8 C7 C9 90.3(4) . . ?
C11 C9 C7 103.3(4) . . ?
C11 C9 C10 107.6(5) . . ?
C19 C9 C11 114.1(4) . . ?
C19 C9 C7 120.8(5) . . ?
C19 C9 C10 118.1(5) . . ?
C7 C9 C10 89.6(4) . . ?
C19 C12 C20 90.2(4) . . ?
C13 C12 C19 108.2(5) . . ?
C13 C12 C20 102.9(5) . . ?
C22 C13 C12 102.2(5) . . ?
C14 C13 C12 102.7(5) . . ?
C14 C13 C22 104.1(5) . . ?
C15 C16 C22 102.9(5) . . ?
C17 C16 C22 107.3(4) . . ?
C17 C16 C15 103.6(5) . . ?
C21 C22 C13 102.8(5) . . ?
C21 C22 C16 108.2(4) . . ?
C13 C22 C16 102.0(5) . . ?
C8 C10 C9 88.7(4) . . ?
C1 C10 C9 108.0(5) . . ?
C1 C10 C8 103.2(4) . . ?
C11 C6 C5 103.0(4) . . ?
C11 C6 C2 108.1(5) . . ?
C5 C6 C2 102.8(4) . . ?
C1 C2 C6 108.4(4) . . ?
C1 C2 C3 103.0(5) . . ?
C3 C2 C6 102.7(5) . . ?
C7 C8 C10 91.4(4) . . ?
C7 C8 C3 103.2(5) . . ?
C10 C8 C3 108.2(5) . . ?
C16 C15 C20 101.2(5) . . ?
C14 C15 C16 104.5(5) . . ?
C14 C15 C20 102.4(5) . . ?
O1 C1 C10 127.2(6) . . ?
O1 C1 C2 126.8(6) . . ?
C2 C1 C10 105.9(5) . . ?
C15 C14 C13 95.8(5) . . ?
C2 C3 C8 100.9(4) . . ?
C4 C3 C2 103.7(5) . . ?
C4 C3 C8 102.8(5) . . ?
O3 C17 C16 126.8(6) . . ?
O3 C17 C18 127.6(6) . . ?
C16 C17 C18 105.5(6) . . ?
C17 C18 C19 108.5(5) . . ?
C17 C18 C20 103.0(5) . . ?
C20 C18 C19 88.7(4) . . ?
C3 C4 C5 95.8(5) . . ?
C12 C20 C15 103.4(5) . . ?
C18 C20 C12 91.2(4) . . ?
C18 C20 C15 108.6(5) . . ?

_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 1.385
_oxdiff_exptl_absorpt_empirical_full_min 0.562
####################################################################### 
# 
# 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_61
_database_code_depnum_ccdc_archive 'CCDC 1936541'
loop_
_audit_author_name
_audit_author_address
'Yijun Shi'
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2019-06-26 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;
_audit_creation_date             2018-09-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H9 O2'
_chemical_formula_sum            'C11 H9 O2'
_chemical_formula_weight         173.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N O'
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                   10.8929(6)
_cell_length_b                   8.8947(5)
_cell_length_c                   15.6600(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1517.28(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1496
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      28.0420
_cell_measurement_theta_min      4.3800
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.516
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4706
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.099
_diffrn_reflns_theta_min         3.741
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3376
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  81.00   1.00    2.50    --   10.20  38.00 -60.00   78
  2  ω    -45.00   5.00   1.00    2.50    --  -10.51  19.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0006514000
_diffrn_orient_matrix_UB_12      0.0796434000
_diffrn_orient_matrix_UB_13      -0.0022056000
_diffrn_orient_matrix_UB_21      -0.0615972000
_diffrn_orient_matrix_UB_22      -0.0004641000
_diffrn_orient_matrix_UB_23      -0.0147026000
_diffrn_orient_matrix_UB_31      -0.0210693000
_diffrn_orient_matrix_UB_32      0.0039531000
_diffrn_orient_matrix_UB_33      0.0427938000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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                1189
_reflns_number_total             1648
_reflns_odcompleteness_completeness 98.20
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1648
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.038
_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)+(0.0478P)²+0.5950P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1188
_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:
 C7(H7), C3(H3), C9(H9), C6(H6), C11(H11), C2(H2), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
;
_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 0.39098(12) 0.27194(16) 0.57365(8) 0.0295(4) Uani 1 1 d . . . . .
O2 O 0.21909(13) 0.37442(17) 0.36330(10) 0.0370(4) Uani 1 1 d . . . . .
C10 C 0.49250(16) 0.4359(2) 0.46910(11) 0.0194(4) Uani 1 1 d . . . . .
C1 C 0.43762(17) 0.2911(2) 0.50442(11) 0.0204(4) Uani 1 1 d . . . . .
C7 C 0.42655(18) 0.4752(2) 0.38086(11) 0.0225(4) Uani 1 1 d . . . . .
H7 H 0.403420 0.580374 0.371589 0.027 Uiso 1 1 calc R . . . .
C3 C 0.60071(18) 0.2011(2) 0.41789(12) 0.0245(5) Uani 1 1 d . . . . .
H3 H 0.658695 0.151440 0.456539 0.029 Uiso 1 1 calc R . . . .
C9 C 0.39964(18) 0.2142(2) 0.34953(12) 0.0242(5) Uani 1 1 d . . . . .
H9 H 0.350175 0.132670 0.325241 0.029 Uiso 1 1 calc R . . . .
C6 C 0.54140(18) 0.4171(2) 0.33239(12) 0.0242(5) Uani 1 1 d . . . . .
H6 H 0.583846 0.488876 0.295225 0.029 Uiso 1 1 calc R . . . .
C11 C 0.60562(17) 0.3756(2) 0.41793(12) 0.0217(4) Uani 1 1 d . . . . .
H11 H 0.685288 0.422503 0.429514 0.026 Uiso 1 1 calc R . . . .
C2 C 0.46375(17) 0.1727(2) 0.43727(12) 0.0229(5) Uani 1 1 d . . . . .
H2 H 0.446476 0.070020 0.456496 0.027 Uiso 1 1 calc R . . . .
C8 C 0.32968(19) 0.3581(2) 0.36340(12) 0.0242(5) Uani 1 1 d . . . . .
C5 C 0.50959(19) 0.2612(2) 0.29349(12) 0.0266(5) Uani 1 1 d . . . . .
H5 H 0.494502 0.260563 0.231801 0.032 Uiso 1 1 calc R . . . .
C4 C 0.6149(2) 0.1614(2) 0.32376(13) 0.0310(5) Uani 1 1 d . . . . .
H4A H 0.600595 0.055694 0.312374 0.037 Uiso 1 1 calc R . . . .
H4B H 0.693650 0.191997 0.300641 0.037 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.209(2) . ?
O2 C8 1.213(2) . ?
C10 C10 1.504(4) 5_666 ?
C10 C1 1.524(3) . ?
C10 C7 1.596(2) . ?
C10 C11 1.565(3) . ?
C1 C2 1.515(3) . ?
C7 C6 1.552(3) . ?
C7 C8 1.508(3) . ?
C3 C11 1.553(3) . ?
C3 C2 1.543(3) . ?
C3 C4 1.523(3) . ?
C9 C2 1.585(3) . ?
C9 C8 1.505(3) . ?
C9 C5 1.543(3) . ?
C6 C11 1.556(3) . ?
C6 C5 1.554(3) . ?
C5 C4 1.526(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 C10 C1 116.72(19) 5_666 . ?
C10 C10 C7 116.11(19) 5_666 . ?
C10 C10 C11 120.25(19) 5_666 . ?
C1 C10 C7 108.82(14) . . ?
C1 C10 C11 101.82(14) . . ?
C11 C10 C7 89.20(13) . . ?
O1 C1 C10 127.54(17) . . ?
O1 C1 C2 127.10(17) . . ?
C2 C1 C10 105.18(15) . . ?
C6 C7 C10 89.30(14) . . ?
C8 C7 C10 108.72(15) . . ?
C8 C7 C6 104.22(15) . . ?
C2 C3 C11 101.34(15) . . ?
C4 C3 C11 103.19(16) . . ?
C4 C3 C2 104.51(16) . . ?
C8 C9 C2 107.20(15) . . ?
C8 C9 C5 104.15(16) . . ?
C5 C9 C2 102.37(15) . . ?
C7 C6 C11 91.17(13) . . ?
C7 C6 C5 108.01(16) . . ?
C5 C6 C11 103.06(15) . . ?
C3 C11 C10 108.42(15) . . ?
C3 C11 C6 102.79(15) . . ?
C6 C11 C10 90.31(14) . . ?
C1 C2 C3 101.80(15) . . ?
C1 C2 C9 110.93(15) . . ?
C3 C2 C9 102.56(14) . . ?
O2 C8 C7 127.77(19) . . ?
O2 C8 C9 127.17(19) . . ?
C9 C8 C7 105.02(16) . . ?
C9 C5 C6 101.08(15) . . ?
C4 C5 C9 104.44(16) . . ?
C4 C5 C6 103.27(16) . . ?
C3 C4 C5 95.15(15) . . ?

_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 1.071
_oxdiff_exptl_absorpt_empirical_full_min 0.922
####################################################################### 
# 
# 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_14
_database_code_depnum_ccdc_archive 'CCDC 1936543'
loop_
_audit_author_name
_audit_author_address
'Yijun Shi'
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2019-06-26 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;
_audit_creation_date             2018-10-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H22 O4'
_chemical_formula_sum            'C26 H22 O4'
_chemical_formula_weight         398.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.2415(4)
_cell_length_b                   11.3298(5)
_cell_length_c                   8.8293(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.639(4)
_cell_angle_gamma                90
_cell_volume                     924.41(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3177
_cell_measurement_temperature    199.98(10)
_cell_measurement_theta_max      29.2120
_cell_measurement_theta_min      4.2520
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7839
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.100
_diffrn_reflns_theta_min         3.597
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3376
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  80.00   1.00   10.00    --    9.81  57.00-120.00   97
  2  ω    -37.00  60.00   1.00   10.00    --  -10.12  57.00  90.00   97
  3  ω    -80.00  17.00   1.00   10.00    --  -10.12 -57.00 -60.00   97
  4  ω    -33.00  -8.00   1.00   10.00    --  -10.12  38.00 -60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0379739000
_diffrn_orient_matrix_UB_12      0.0357950000
_diffrn_orient_matrix_UB_13      0.0521165000
_diffrn_orient_matrix_UB_21      0.0107310000
_diffrn_orient_matrix_UB_22      -0.0432971000
_diffrn_orient_matrix_UB_23      0.0570989000
_diffrn_orient_matrix_UB_31      0.0658677000
_diffrn_orient_matrix_UB_32      0.0276242000
_diffrn_orient_matrix_UB_33      0.0217705000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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                1644
_reflns_number_total             2020
_reflns_odcompleteness_completeness 98.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2020
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      1.038
_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)+(0.0505P)²+0.3974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1152
_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:
 C9(H9), C8(H8), C10(H10), C4(H4), C5(H5), C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C12(H12A,H12B)
;
_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 0.29409(14) 0.21860(10) 0.63163(14) 0.0345(3) Uani 1 1 d . . . . .
O2 O 0.61998(12) 0.40243(11) 0.74028(13) 0.0325(3) Uani 1 1 d . . . . .
C6 C 0.44546(15) 0.49125(13) 0.56142(16) 0.0194(3) Uani 1 1 d . . . . .
C7 C 0.50307(15) 0.44605(13) 0.71401(17) 0.0213(3) Uani 1 1 d . . . . .
C1 C 0.28077(16) 0.32442(14) 0.64071(17) 0.0230(3) Uani 1 1 d . . . . .
C9 C 0.38298(16) 0.47045(14) 0.82565(16) 0.0216(3) Uani 1 1 d . . . . .
H9 H 0.412663 0.460518 0.931793 0.026 Uiso 1 1 calc R . . . .
C11 C 0.17656(16) 0.60035(14) 0.81154(17) 0.0228(4) Uani 1 1 d . . . . .
C8 C 0.24284(16) 0.39599(13) 0.77955(16) 0.0212(3) Uani 1 1 d . . . . .
H8 H 0.203244 0.348962 0.862524 0.025 Uiso 1 1 calc R . . . .
C10 C 0.33799(16) 0.59784(13) 0.78511(17) 0.0215(3) Uani 1 1 d . . . . .
H10 H 0.394045 0.660552 0.834772 0.026 Uiso 1 1 calc R . . . .
C4 C 0.13895(16) 0.49229(14) 0.71932(17) 0.0216(3) Uani 1 1 d . . . . .
H4 H 0.036208 0.470920 0.715818 0.026 Uiso 1 1 calc R . . . .
C5 C 0.34468(15) 0.59510(13) 0.60922(16) 0.0199(3) Uani 1 1 d . . . . .
H5 H 0.358057 0.670781 0.557491 0.024 Uiso 1 1 calc R . . . .
C2 C 0.30536(16) 0.41497(13) 0.51765(17) 0.0218(3) Uani 1 1 d . . . . .
H2 H 0.297059 0.387593 0.412621 0.026 Uiso 1 1 calc R . . . .
C3 C 0.20866(16) 0.52151(13) 0.56392(17) 0.0214(3) Uani 1 1 d . . . . .
H3 H 0.144903 0.554703 0.485379 0.026 Uiso 1 1 calc R . . . .
C13 C 0.1070(2) 0.63962(16) 0.95498(19) 0.0327(4) Uani 1 1 d . . . . .
H13A H 0.169247 0.670066 1.035054 0.039 Uiso 1 1 calc R . . . .
H13B H 0.023260 0.595983 0.989432 0.039 Uiso 1 1 calc R . . . .
C12 C 0.09052(19) 0.71248(15) 0.8124(2) 0.0320(4) Uani 1 1 d . . . . .
H12A H -0.003004 0.712373 0.761402 0.038 Uiso 1 1 calc R . . . .
H12B H 0.143011 0.786470 0.807033 0.038 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2079(19) . ?
O2 C7 1.2082(18) . ?
C6 C6 1.502(3) 3_666 ?
C6 C7 1.531(2) . ?
C6 C5 1.562(2) . ?
C6 C2 1.600(2) . ?
C7 C9 1.518(2) . ?
C1 C8 1.514(2) . ?
C1 C2 1.513(2) . ?
C9 C8 1.595(2) . ?
C9 C10 1.543(2) . ?
C11 C10 1.513(2) . ?
C11 C4 1.509(2) . ?
C11 C13 1.494(2) . ?
C11 C12 1.499(2) . ?
C8 C4 1.544(2) . ?
C10 C5 1.555(2) . ?
C4 C3 1.558(2) . ?
C5 C3 1.557(2) . ?
C2 C3 1.559(2) . ?
C13 C12 1.512(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C6 C7 116.74(15) 3_666 . ?
C6 C6 C5 120.18(16) 3_666 . ?
C6 C6 C2 116.40(15) 3_666 . ?
C7 C6 C5 102.52(11) . . ?
C7 C6 C2 107.71(11) . . ?
C5 C6 C2 89.36(11) . . ?
O2 C7 C6 127.38(13) . . ?
O2 C7 C9 127.48(14) . . ?
C9 C7 C6 105.12(12) . . ?
O1 C1 C8 127.58(14) . . ?
O1 C1 C2 127.51(14) . . ?
C2 C1 C8 104.85(12) . . ?
C7 C9 C8 109.60(12) . . ?
C7 C9 C10 102.52(12) . . ?
C10 C9 C8 102.69(11) . . ?
C4 C11 C10 97.07(12) . . ?
C13 C11 C10 124.80(14) . . ?
C13 C11 C4 126.89(14) . . ?
C13 C11 C12 60.67(11) . . ?
C12 C11 C10 122.74(13) . . ?
C12 C11 C4 124.85(14) . . ?
C1 C8 C9 107.17(11) . . ?
C1 C8 C4 104.37(12) . . ?
C4 C8 C9 102.37(12) . . ?
C9 C10 C5 101.50(11) . . ?
C11 C10 C9 104.20(12) . . ?
C11 C10 C5 101.81(12) . . ?
C11 C4 C8 104.41(12) . . ?
C11 C4 C3 102.00(12) . . ?
C8 C4 C3 101.06(11) . . ?
C10 C5 C6 108.38(12) . . ?
C10 C5 C3 103.08(11) . . ?
C3 C5 C6 90.54(11) . . ?
C1 C2 C6 108.68(12) . . ?
C1 C2 C3 104.22(12) . . ?
C3 C2 C6 89.04(11) . . ?
C4 C3 C2 108.07(12) . . ?
C5 C3 C4 103.19(11) . . ?
C5 C3 C2 91.05(11) . . ?
C11 C13 C12 59.81(11) . . ?
C11 C12 C13 59.52(11) . . ?

_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 1.225
_oxdiff_exptl_absorpt_empirical_full_min 0.800
