# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_190314ZBB_0m
_database_code_depnum_ccdc_archive 'CCDC 2036722'
loop_
_audit_author_name
_audit_author_address
Phenanthrene
;Huaibei Normal University 
China
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2020-12-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 O3, C4 H8 O2'
_chemical_formula_sum            'C28 H26 O5'
_chemical_formula_weight         442.49

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

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

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

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

_cell_length_a                   8.688(2)
_cell_length_b                   10.010(2)
_cell_length_c                   13.325(3)
_cell_angle_alpha                92.124(3)
_cell_angle_beta                 91.235(3)
_cell_angle_gamma                100.763(3)
_cell_volume                     1137.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2706
_cell_measurement_theta_min      2.3871
_cell_measurement_theta_max      25.8439

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8054
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.530
_diffrn_reflns_theta_max         25.100
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             4037
_reflns_number_gt                2879
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0535P)²+0.1999P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.025(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4037
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1118
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2665(2) 0.43827(18) 0.85536(13) 0.0423(4) Uani 1 1 d . . . . .
C2 C 0.20217(18) 0.29105(16) 0.84251(11) 0.0365(4) Uani 1 1 d . . . . .
C3 C 0.23010(19) 0.18214(17) 0.90382(12) 0.0381(4) Uani 1 1 d . . . . .
C4 C 0.3335(2) 0.21062(19) 0.98756(12) 0.0458(4) Uani 1 1 d . . . . .
H4 H 0.3886 0.2988 1.0003 0.055 Uiso 1 1 calc R U . . .
C5 C 0.3543(2) 0.1103(2) 1.05078(13) 0.0499(5) Uani 1 1 d . . . . .
C6 C 0.2696(2) -0.0199(2) 1.02757(14) 0.0552(5) Uani 1 1 d . . . . .
H6 H 0.2812 -0.0879 1.0712 0.066 Uiso 1 1 calc R U . . .
C7 C 0.1699(2) -0.05600(18) 0.94503(13) 0.0473(5) Uani 1 1 d . . . . .
C8 C 0.14680(19) 0.04745(16) 0.87765(12) 0.0389(4) Uani 1 1 d . . . . .
C9 C 0.04611(18) 0.02598(16) 0.78592(12) 0.0389(4) Uani 1 1 d . . . . .
C10 C -0.0326(2) -0.10203(19) 0.74658(16) 0.0583(5) Uani 1 1 d . . . . .
H10 H -0.0234 -0.1793 0.7811 0.070 Uiso 1 1 calc R U . . .
C11 C -0.1222(2) -0.1170(2) 0.65946(17) 0.0652(6) Uani 1 1 d . . . . .
H11 H -0.1711 -0.2037 0.6365 0.078 Uiso 1 1 calc R U . . .
C12 C -0.1416(2) -0.00637(19) 0.60512(16) 0.0586(5) Uani 1 1 d . . . . .
H12 H -0.2030 -0.0179 0.5463 0.070 Uiso 1 1 calc R U . . .
C13 C -0.0689(2) 0.11991(18) 0.63934(14) 0.0502(5) Uani 1 1 d . . . . .
H13 H -0.0815 0.1953 0.6036 0.060 Uiso 1 1 calc R U . . .
C14 C 0.02487(19) 0.13833(16) 0.72772(12) 0.0378(4) Uani 1 1 d . . . . .
C15 C 0.10504(18) 0.27064(16) 0.76120(11) 0.0361(4) Uani 1 1 d . . . . .
C16 C 0.09756(19) 0.40512(16) 0.71415(12) 0.0385(4) Uani 1 1 d . . . . .
C17 C -0.06085(19) 0.44792(15) 0.72062(12) 0.0376(4) Uani 1 1 d . . . . .
C18 C -0.1300(2) 0.45437(19) 0.81334(13) 0.0517(5) Uani 1 1 d . . . . .
H18 H -0.0784 0.4330 0.8708 0.062 Uiso 1 1 calc R U . . .
C19 C -0.2740(2) 0.4921(2) 0.82120(15) 0.0602(5) Uani 1 1 d . . . . .
H19 H -0.3195 0.4956 0.8835 0.072 Uiso 1 1 calc R U . . .
C20 C -0.3505(2) 0.52463(18) 0.73629(16) 0.0559(5) Uani 1 1 d . . . . .
H20 H -0.4475 0.5505 0.7414 0.067 Uiso 1 1 calc R U . . .
C21 C -0.2836(2) 0.51889(17) 0.64453(14) 0.0498(5) Uani 1 1 d . . . . .
H21 H -0.3353 0.5409 0.5874 0.060 Uiso 1 1 calc R U . . .
C22 C -0.1389(2) 0.48036(17) 0.63637(13) 0.0429(4) Uani 1 1 d . . . . .
H22 H -0.0944 0.4764 0.5738 0.052 Uiso 1 1 calc R U . . .
C23 C 0.4610(3) 0.1397(2) 1.14264(14) 0.0690(6) Uani 1 1 d . . . . .
H23A H 0.5288 0.2265 1.1374 0.103 Uiso 1 1 calc R U . . .
H23B H 0.5229 0.0701 1.1476 0.103 Uiso 1 1 calc R U . . .
H23C H 0.3993 0.1413 1.2014 0.103 Uiso 1 1 calc R U . . .
C24 C 0.0920(3) -0.2047(2) 0.93451(17) 0.0741(7) Uani 1 1 d . . . . .
H24A H 0.1153 -0.2504 0.9934 0.111 Uiso 1 1 calc R U . . .
H24B H 0.1306 -0.2462 0.8765 0.111 Uiso 1 1 calc R U . . .
H24C H -0.0194 -0.2116 0.9269 0.111 Uiso 1 1 calc R U . . .
C25 C 0.4962(3) 0.1600(2) 0.68524(16) 0.0748(7) Uani 1 1 d . . . . .
H25A H 0.5507 0.2297 0.7314 0.112 Uiso 1 1 calc R U . . .
H25B H 0.5536 0.0870 0.6795 0.112 Uiso 1 1 calc R U . . .
H25C H 0.3936 0.1259 0.7095 0.112 Uiso 1 1 calc R U . . .
C26 C 0.4815(2) 0.21745(19) 0.58541(14) 0.0509(5) Uani 1 1 d . . . . .
C27 C 0.5953(3) 0.2503(2) 0.42581(14) 0.0646(6) Uani 1 1 d . . . . .
H27A H 0.6007 0.3479 0.4324 0.077 Uiso 1 1 calc R U . . .
H27B H 0.5013 0.2104 0.3869 0.077 Uiso 1 1 calc R U . . .
C28 C 0.7358(3) 0.2198(2) 0.37553(16) 0.0739(6) Uani 1 1 d . . . . .
H28A H 0.8283 0.2632 0.4131 0.111 Uiso 1 1 calc R U . . .
H28B H 0.7390 0.2532 0.3089 0.111 Uiso 1 1 calc R U . . .
H28C H 0.7313 0.1232 0.3720 0.111 Uiso 1 1 calc R U . . .
O1 O 0.35422(16) 0.50225(13) 0.91824(10) 0.0605(4) Uani 1 1 d . . . . .
O2 O 0.20811(13) 0.50230(11) 0.77867(8) 0.0461(3) Uani 1 1 d . . . . .
O3 O 0.14792(14) 0.41378(12) 0.61624(8) 0.0482(3) Uani 1 1 d . . . . .
H3 H 0.2166 0.3685 0.6086 0.072 Uiso 1 1 calc R U . . .
O4 O 0.38311(16) 0.28066(16) 0.56009(11) 0.0717(4) Uani 1 1 d . . . . .
O5 O 0.59226(15) 0.19276(13) 0.52423(9) 0.0571(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.2015(19) . ?
C1 O2 1.364(2) . ?
C1 C2 1.478(2) . ?
C2 C15 1.344(2) . ?
C2 C3 1.439(2) . ?
C3 C4 1.404(2) . ?
C3 C8 1.433(2) . ?
C4 C5 1.369(2) . ?
C5 C6 1.392(3) . ?
C5 C23 1.506(3) . ?
C6 C7 1.380(3) . ?
C7 C8 1.434(2) . ?
C7 C24 1.515(3) . ?
C8 C9 1.473(2) . ?
C9 C10 1.411(2) . ?
C9 C14 1.427(2) . ?
C10 C11 1.371(3) . ?
C11 C12 1.379(3) . ?
C12 C13 1.361(2) . ?
C13 C14 1.404(2) . ?
C14 C15 1.427(2) . ?
C15 C16 1.518(2) . ?
C16 O3 1.3856(19) . ?
C16 O2 1.4702(19) . ?
C16 C17 1.519(2) . ?
C17 C22 1.379(2) . ?
C17 C18 1.390(2) . ?
C18 C19 1.378(3) . ?
C19 C20 1.380(3) . ?
C20 C21 1.369(3) . ?
C21 C22 1.387(2) . ?
C25 C26 1.481(3) . ?
C26 O4 1.205(2) . ?
C26 O5 1.326(2) . ?
C27 O5 1.451(2) . ?
C27 C28 1.480(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 120.54(16) . . ?
O1 C1 C2 131.40(16) . . ?
O2 C1 C2 108.06(14) . . ?
C15 C2 C3 122.75(15) . . ?
C15 C2 C1 108.43(14) . . ?
C3 C2 C1 128.81(15) . . ?
C4 C3 C8 122.31(15) . . ?
C4 C3 C2 119.78(16) . . ?
C8 C3 C2 117.88(15) . . ?
C5 C4 C3 120.90(18) . . ?
C4 C5 C6 116.98(17) . . ?
C4 C5 C23 121.65(19) . . ?
C6 C5 C23 121.35(17) . . ?
C7 C6 C5 125.24(17) . . ?
C6 C7 C8 118.66(17) . . ?
C6 C7 C24 115.85(16) . . ?
C8 C7 C24 125.48(18) . . ?
C3 C8 C7 115.83(16) . . ?
C3 C8 C9 118.60(14) . . ?
C7 C8 C9 125.57(16) . . ?
C10 C9 C14 114.57(16) . . ?
C10 C9 C8 124.84(16) . . ?
C14 C9 C8 120.57(15) . . ?
C11 C10 C9 122.61(18) . . ?
C10 C11 C12 121.55(18) . . ?
C13 C12 C11 118.62(18) . . ?
C12 C13 C14 121.16(17) . . ?
C13 C14 C15 120.78(15) . . ?
C13 C14 C9 121.48(16) . . ?
C15 C14 C9 117.72(15) . . ?
C2 C15 C14 122.31(15) . . ?
C2 C15 C16 110.22(14) . . ?
C14 C15 C16 127.47(14) . . ?
O3 C16 O2 108.58(13) . . ?
O3 C16 C15 114.40(13) . . ?
O2 C16 C15 102.23(12) . . ?
O3 C16 C17 109.69(13) . . ?
O2 C16 C17 106.94(12) . . ?
C15 C16 C17 114.35(13) . . ?
C22 C17 C18 118.77(16) . . ?
C22 C17 C16 121.62(15) . . ?
C18 C17 C16 119.61(15) . . ?
C19 C18 C17 120.77(17) . . ?
C18 C19 C20 119.80(18) . . ?
C21 C20 C19 120.01(18) . . ?
C20 C21 C22 120.30(17) . . ?
C17 C22 C21 120.35(16) . . ?
O4 C26 O5 122.11(18) . . ?
O4 C26 C25 125.71(19) . . ?
O5 C26 C25 112.17(17) . . ?
O5 C27 C28 107.32(16) . . ?
C1 O2 C16 110.98(12) . . ?
C26 O5 C27 117.32(15) . . ?

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.035

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_181226ZBB_0m
_database_code_depnum_ccdc_archive 'CCDC 2036730'
loop_
_audit_author_name
_audit_author_address
butenolide
;Huaibei Normal University 
China
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2020-12-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H15 Cl O3'
_chemical_formula_sum            'C22 H15 Cl O3'
_chemical_formula_weight         362.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.6353(12)
_cell_length_b                   9.3840(10)
_cell_length_c                   18.823(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.275(2)
_cell_angle_gamma                90
_cell_volume                     1835.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2705
_cell_measurement_theta_min      2.4366
_cell_measurement_theta_max      24.1922

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.226
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_process_details   SADABS


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9120
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.437
_diffrn_reflns_theta_max         25.095
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3251
_reflns_number_gt                2267
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;


_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+0.2439P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3251
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1079
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6298(2) 0.7082(2) 0.97770(11) 0.0626(6) Uani 1 1 d . . . . .
C2 C 0.67819(19) 0.5735(2) 0.99333(10) 0.0582(5) Uani 1 1 d . . . . .
H2 H 0.7432 0.5576 1.0342 0.070 Uiso 1 1 calc R U . . .
C3 C 0.62944(17) 0.4616(2) 0.94774(9) 0.0490(5) Uani 1 1 d . . . . .
H3A H 0.6621 0.3702 0.9580 0.059 Uiso 1 1 calc R U . . .
C4 C 0.53220(16) 0.48493(19) 0.88691(9) 0.0447(4) Uani 1 1 d . . . . .
C5 C 0.4848(2) 0.6223(2) 0.87289(11) 0.0605(5) Uani 1 1 d . . . . .
H5 H 0.4191 0.6390 0.8325 0.073 Uiso 1 1 calc R U . . .
C6 C 0.5332(2) 0.7343(2) 0.91764(12) 0.0687(6) Uani 1 1 d . . . . .
H6 H 0.5013 0.8260 0.9075 0.082 Uiso 1 1 calc R U . . .
C7 C 0.47770(17) 0.36639(19) 0.83843(9) 0.0436(4) Uani 1 1 d . . . . .
C8 C 0.53333(16) 0.25801(18) 0.81084(9) 0.0411(4) Uani 1 1 d . . . . .
C9 C 0.33655(18) 0.3516(2) 0.81209(9) 0.0476(5) Uani 1 1 d . . . . .
C10 C 0.43112(16) 0.1719(2) 0.75969(9) 0.0446(4) Uani 1 1 d . . . . .
C11 C 0.67030(16) 0.21666(18) 0.82137(9) 0.0423(4) Uani 1 1 d . . . . .
C12 C 0.7524(2) 0.2899(2) 0.78717(14) 0.0692(6) Uani 1 1 d . . . . .
H12 H 0.7236 0.3703 0.7596 0.083 Uiso 1 1 calc R U . . .
C13 C 0.8785(2) 0.2436(3) 0.79381(17) 0.0879(8) Uani 1 1 d . . . . .
H13 H 0.9334 0.2924 0.7699 0.105 Uiso 1 1 calc R U . . .
C14 C 0.9223(2) 0.1280(3) 0.83491(16) 0.0833(8) Uani 1 1 d . . . . .
H14 H 1.0071 0.0985 0.8395 0.100 Uiso 1 1 calc R U . . .
C15 C 0.8424(2) 0.0554(3) 0.86918(13) 0.0767(7) Uani 1 1 d . . . . .
H15 H 0.8727 -0.0236 0.8975 0.092 Uiso 1 1 calc R U . . .
C16 C 0.71584(19) 0.0985(2) 0.86228(11) 0.0605(6) Uani 1 1 d . . . . .
H16 H 0.6612 0.0474 0.8854 0.073 Uiso 1 1 calc R U . . .
C17 C 0.43969(16) 0.18993(19) 0.68047(9) 0.0439(4) Uani 1 1 d . . . . .
C18 C 0.36436(19) 0.2857(2) 0.63446(10) 0.0560(5) Uani 1 1 d . . . . .
H18 H 0.3050 0.3416 0.6516 0.067 Uiso 1 1 calc R U . . .
C19 C 0.3763(2) 0.2992(2) 0.56328(11) 0.0688(6) Uani 1 1 d . . . . .
H19 H 0.3248 0.3639 0.5328 0.083 Uiso 1 1 calc R U . . .
C20 C 0.4627(3) 0.2185(3) 0.53725(12) 0.0749(7) Uani 1 1 d . . . . .
H20 H 0.4701 0.2277 0.4891 0.090 Uiso 1 1 calc R U . . .
C21 C 0.5387(2) 0.1238(3) 0.58229(13) 0.0769(7) Uani 1 1 d . . . . .
H21 H 0.5980 0.0686 0.5647 0.092 Uiso 1 1 calc R U . . .
C22 C 0.5279(2) 0.1097(2) 0.65380(11) 0.0614(5) Uani 1 1 d . . . . .
H22 H 0.5805 0.0456 0.6841 0.074 Uiso 1 1 calc R U . . .
Cl1 Cl 0.68940(9) 0.84856(7) 1.03566(4) 0.1055(3) Uani 1 1 d . . . . .
O1 O 0.25133(12) 0.42593(16) 0.82474(7) 0.0618(4) Uani 1 1 d . . . . .
O2 O 0.31095(11) 0.23653(14) 0.76895(7) 0.0530(3) Uani 1 1 d . . . . .
O3 O 0.43531(12) 0.03161(13) 0.78227(7) 0.0540(4) Uani 1 1 d . . . . .
H3 H 0.3867 -0.0163 0.7518 0.081 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
C1 C2 1.373(3) . ?
C1 C6 1.378(3) . ?
C1 Cl1 1.741(2) . ?
C2 C3 1.385(3) . ?
C3 C4 1.387(2) . ?
C4 C5 1.389(3) . ?
C4 C7 1.477(2) . ?
C5 C6 1.376(3) . ?
C7 C8 1.336(2) . ?
C7 C9 1.484(3) . ?
C8 C11 1.480(2) . ?
C8 C10 1.522(2) . ?
C9 O1 1.207(2) . ?
C9 O2 1.344(2) . ?
C10 O3 1.381(2) . ?
C10 O2 1.458(2) . ?
C10 C17 1.523(2) . ?
C11 C12 1.374(3) . ?
C11 C16 1.378(3) . ?
C12 C13 1.391(3) . ?
C13 C14 1.356(4) . ?
C14 C15 1.354(4) . ?
C15 C16 1.385(3) . ?
C17 C18 1.380(2) . ?
C17 C22 1.378(3) . ?
C18 C19 1.378(3) . ?
C19 C20 1.360(3) . ?
C20 C21 1.367(3) . ?
C21 C22 1.381(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
C2 C1 C6 121.3(2) . . ?
C2 C1 Cl1 119.47(18) . . ?
C6 C1 Cl1 119.22(18) . . ?
C1 C2 C3 119.43(19) . . ?
C2 C3 C4 120.44(18) . . ?
C3 C4 C5 118.68(18) . . ?
C3 C4 C7 121.12(16) . . ?
C5 C4 C7 120.19(16) . . ?
C6 C5 C4 121.29(19) . . ?
C5 C6 C1 118.9(2) . . ?
C8 C7 C4 131.72(16) . . ?
C8 C7 C9 107.41(16) . . ?
C4 C7 C9 120.87(16) . . ?
C7 C8 C11 130.72(16) . . ?
C7 C8 C10 109.53(15) . . ?
C11 C8 C10 119.73(15) . . ?
O1 C9 O2 121.30(17) . . ?
O1 C9 C7 128.97(18) . . ?
O2 C9 C7 109.73(15) . . ?
O3 C10 O2 109.35(14) . . ?
O3 C10 C8 109.84(14) . . ?
O2 C10 C8 103.29(13) . . ?
O3 C10 C17 113.74(15) . . ?
O2 C10 C17 107.90(14) . . ?
C8 C10 C17 112.16(14) . . ?
C12 C11 C16 118.80(17) . . ?
C12 C11 C8 120.76(17) . . ?
C16 C11 C8 120.33(16) . . ?
C11 C12 C13 119.9(2) . . ?
C14 C13 C12 120.6(2) . . ?
C15 C14 C13 120.0(2) . . ?
C14 C15 C16 120.3(2) . . ?
C11 C16 C15 120.4(2) . . ?
C18 C17 C22 118.45(18) . . ?
C18 C17 C10 122.64(16) . . ?
C22 C17 C10 118.89(17) . . ?
C19 C18 C17 120.6(2) . . ?
C20 C19 C18 120.6(2) . . ?
C19 C20 C21 119.6(2) . . ?
C20 C21 C22 120.4(2) . . ?
C17 C22 C21 120.4(2) . . ?
C9 O2 C10 109.65(13) . . ?

_refine_diff_density_max         0.134
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.033

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2036729'
loop_
_audit_author_name
_audit_author_address
hydroxybutenolide
;Huaibei Normal University 
China
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2020-12-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H16 O3'
_chemical_formula_sum            'C22 H16 O3'
_chemical_formula_weight         328.35

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   11.442(5)
_cell_length_b                   16.968(7)
_cell_length_c                   8.274(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1606.5(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2663
_cell_measurement_theta_min      2.7387
_cell_measurement_theta_max      26.0582

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7834
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.147
_diffrn_reflns_theta_max         25.099
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             2825
_reflns_number_gt                2461
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.956

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0410P)²+0.0733P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1013 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.4(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2825
_refine_ls_number_parameters     227
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0806
_refine_ls_wR_factor_gt          0.0757
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7773(2) 0.28814(13) 0.4595(3) 0.0409(6) Uani 1 1 d . . . . .
C2 C 0.7063(2) 0.23264(17) 0.5300(4) 0.0556(7) Uani 1 1 d . . . . .
H2 H 0.6387 0.2162 0.4775 0.067 Uiso 1 1 calc R U . . .
C3 C 0.7353(3) 0.20127(18) 0.6785(4) 0.0646(9) Uani 1 1 d . . . . .
H3 H 0.6869 0.1635 0.7250 0.077 Uiso 1 1 calc R U . . .
C4 C 0.8329(3) 0.22459(18) 0.7579(4) 0.0590(8) Uani 1 1 d . . . . .
H4 H 0.8509 0.2040 0.8590 0.071 Uiso 1 1 calc R U . . .
C5 C 0.9041(3) 0.27865(16) 0.6873(4) 0.0617(8) Uani 1 1 d . . . . .
H5 H 0.9717 0.2947 0.7403 0.074 Uiso 1 1 calc R U . . .
C6 C 0.8776(2) 0.30991(16) 0.5390(4) 0.0543(7) Uani 1 1 d . . . . .
H6 H 0.9280 0.3462 0.4917 0.065 Uiso 1 1 calc R U . . .
C7 C 0.7453(2) 0.32748(14) 0.3018(3) 0.0407(6) Uani 1 1 d . . . . .
C8 C 0.6979(2) 0.40962(13) 0.3325(3) 0.0354(5) Uani 1 1 d . . . . .
C9 C 0.7732(2) 0.47364(13) 0.3908(3) 0.0362(6) Uani 1 1 d . . . . .
C10 C 0.8829(2) 0.48605(14) 0.3240(4) 0.0485(7) Uani 1 1 d . . . . .
H10 H 0.9090 0.4541 0.2402 0.058 Uiso 1 1 calc R U . . .
C11 C 0.9532(2) 0.54581(17) 0.3817(5) 0.0604(9) Uani 1 1 d . . . . .
H11 H 1.0273 0.5531 0.3381 0.073 Uiso 1 1 calc R U . . .
C12 C 0.9154(3) 0.59390(17) 0.5010(4) 0.0613(9) Uani 1 1 d . . . . .
H12 H 0.9630 0.6344 0.5383 0.074 Uiso 1 1 calc R U . . .
C13 C 0.8073(3) 0.58298(16) 0.5666(4) 0.0560(8) Uani 1 1 d . . . . .
H13 H 0.7811 0.6162 0.6483 0.067 Uiso 1 1 calc R U . . .
C14 C 0.7372(2) 0.52298(14) 0.5123(3) 0.0444(6) Uani 1 1 d . . . . .
H14 H 0.6639 0.5156 0.5587 0.053 Uiso 1 1 calc R U . . .
C15 C 0.5828(2) 0.40873(13) 0.3074(3) 0.0360(5) Uani 1 1 d . . . . .
C16 C 0.5525(2) 0.33158(14) 0.2405(3) 0.0407(6) Uani 1 1 d . . . . .
C17 C 0.4908(2) 0.46788(14) 0.3333(3) 0.0363(5) Uani 1 1 d . . . . .
C18 C 0.5053(2) 0.54606(15) 0.2909(3) 0.0427(6) Uani 1 1 d . . . . .
H18 H 0.5747 0.5626 0.2432 0.051 Uiso 1 1 calc R U . . .
C19 C 0.4174(2) 0.59924(16) 0.3190(4) 0.0527(7) Uani 1 1 d . . . . .
H19 H 0.4277 0.6517 0.2895 0.063 Uiso 1 1 calc R U . . .
C20 C 0.3157(2) 0.57642(19) 0.3893(4) 0.0575(8) Uani 1 1 d . . . . .
H20 H 0.2568 0.6130 0.4083 0.069 Uiso 1 1 calc R U . . .
C21 C 0.3004(2) 0.4995(2) 0.4319(4) 0.0568(8) Uani 1 1 d . . . . .
H21 H 0.2309 0.4837 0.4806 0.068 Uiso 1 1 calc R U . . .
C22 C 0.3867(2) 0.44528(16) 0.4036(3) 0.0451(6) Uani 1 1 d . . . . .
H22 H 0.3751 0.3928 0.4319 0.054 Uiso 1 1 calc R U . . .
O1 O 0.83469(16) 0.32810(10) 0.1917(2) 0.0502(5) Uani 1 1 d . . . . .
H1 H 0.8670 0.2850 0.1912 0.075 Uiso 1 1 calc R U . . .
O2 O 0.64713(15) 0.28593(9) 0.2335(3) 0.0473(5) Uani 1 1 d . . . . .
O3 O 0.45842(17) 0.30854(10) 0.1932(3) 0.0555(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.373(4) . ?
C1 C6 1.373(4) . ?
C1 C7 1.511(4) . ?
C2 C3 1.380(5) . ?
C3 C4 1.355(5) . ?
C4 C5 1.359(4) . ?
C5 C6 1.371(5) . ?
C7 O1 1.369(3) . ?
C7 O2 1.442(3) . ?
C7 C8 1.517(3) . ?
C8 C15 1.334(3) . ?
C8 C9 1.468(3) . ?
C9 C14 1.372(4) . ?
C9 C10 1.387(4) . ?
C10 C11 1.380(4) . ?
C11 C12 1.352(5) . ?
C12 C13 1.363(5) . ?
C13 C14 1.372(4) . ?
C15 C16 1.463(3) . ?
C15 C17 1.470(3) . ?
C16 O3 1.210(3) . ?
C16 O2 1.333(3) . ?
C17 C18 1.382(3) . ?
C17 C22 1.380(3) . ?
C18 C19 1.370(4) . ?
C19 C20 1.358(4) . ?
C20 C21 1.364(4) . ?
C21 C22 1.370(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.4(3) . . ?
C2 C1 C7 121.8(3) . . ?
C6 C1 C7 119.8(2) . . ?
C1 C2 C3 120.1(3) . . ?
C4 C3 C2 121.1(3) . . ?
C3 C4 C5 118.9(3) . . ?
C4 C5 C6 120.9(3) . . ?
C5 C6 C1 120.6(3) . . ?
O1 C7 O2 109.0(2) . . ?
O1 C7 C1 113.4(2) . . ?
O2 C7 C1 108.1(2) . . ?
O1 C7 C8 111.8(2) . . ?
O2 C7 C8 103.67(19) . . ?
C1 C7 C8 110.3(2) . . ?
C15 C8 C9 129.7(2) . . ?
C15 C8 C7 108.5(2) . . ?
C9 C8 C7 121.7(2) . . ?
C14 C9 C10 118.1(2) . . ?
C14 C9 C8 121.0(2) . . ?
C10 C9 C8 120.8(2) . . ?
C11 C10 C9 120.1(3) . . ?
C12 C11 C10 120.6(3) . . ?
C11 C12 C13 119.9(3) . . ?
C12 C13 C14 120.1(3) . . ?
C9 C14 C13 121.1(3) . . ?
C8 C15 C16 107.6(2) . . ?
C8 C15 C17 132.6(2) . . ?
C16 C15 C17 119.8(2) . . ?
O3 C16 O2 121.4(2) . . ?
O3 C16 C15 128.5(2) . . ?
O2 C16 C15 110.1(2) . . ?
C18 C17 C22 118.5(2) . . ?
C18 C17 C15 122.2(2) . . ?
C22 C17 C15 119.3(2) . . ?
C19 C18 C17 120.1(2) . . ?
C20 C19 C18 120.9(3) . . ?
C19 C20 C21 119.6(3) . . ?
C20 C21 C22 120.4(3) . . ?
C21 C22 C17 120.5(3) . . ?
C16 O2 C7 109.39(19) . . ?

_refine_diff_density_max         0.114
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.034

_shelxl_version_number           2014-3



