# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_210202g
_database_code_depnum_ccdc_archive 'CCDC 2106765'
loop_
_audit_author_name
_audit_author_address
'Xiaoxun Li'
;Shandong University
China
;
_audit_update_record             
;
2021-09-01 deposited with the CCDC.	2022-05-16 downloaded from the CCDC.
;
_audit_creation_date             2021-02-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        3ae
_chemical_formula_moiety         'C30 H25 F3 O5'
_chemical_formula_sum            'C30 H25 F3 O5'
_chemical_formula_weight         522.50
_chemical_absolute_configuration syn
_chemical_melting_point          482-483
_chemical_oxdiff_formula         CO
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'
F F 0.0727 0.0534 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   11.2248(5)
_cell_length_b                   12.7951(5)
_cell_length_c                   18.2190(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2616.67(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2502
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.6410
_cell_measurement_theta_min      4.1850
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.876
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0996
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23082
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.041
_diffrn_reflns_theta_min         4.222
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     90.00 174.00   1.00    1.50    --  106.49  77.00 150.00   84
  2  ω     60.00  98.00   1.00    0.10    --   48.45  55.00 132.00   38
  3  ω     36.00 120.00   1.00    0.10    --   48.45  38.00  90.00   84
  4  ω    112.00 178.00   1.00    1.50    --  106.49  57.00  30.00   66
  5  ω    153.00 178.00   1.00    1.50    --  106.49  57.00 -90.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0011908000
_diffrn_orient_matrix_UB_12      -0.0352471000
_diffrn_orient_matrix_UB_13      -0.0807889000
_diffrn_orient_matrix_UB_21      -0.1019627000
_diffrn_orient_matrix_UB_22      -0.0767377000
_diffrn_orient_matrix_UB_23      0.0173189000
_diffrn_orient_matrix_UB_31      -0.0920177000
_diffrn_orient_matrix_UB_32      0.0857607000
_diffrn_orient_matrix_UB_33      -0.0178271000
_diffrn_oxdiff_digest_frames     
;
0194f977b54493aa89bc70dab82fb2b56f00027a55e
;
_diffrn_oxdiff_digest_hkl        
;
015183678fa5d8c9abeb3c1b733da9a9ecce1e
;
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4310
_reflns_number_total             4662
_reflns_odcompleteness_completeness 81.97
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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    ?
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1679 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.00(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         4662
_refine_ls_number_restraints     177
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0534
_refine_ls_restrained_S_all      1.190
_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)+(0.0625P)²+0.8060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1323
_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. Restrained distances
 F1B-C23 = F1A-C23 = F1-C23 = F3B-C23 = F3A-C23 = F3-C23 = F2B-C23 = F2A-C23 =
 F2-C23
 1.45 with sigma of 0.01
3. Restrained planarity
 F1, F1A, F1B, F2, F2A, F2B, F3, F3A, F3B
 with sigma of 0.001
4. Uiso/Uaniso restraints and constraints
F1 \\sim F1A \\sim F1B \\sim F2 \\sim F2A \\sim F2B \\sim F3 \\sim F3A \\sim
F3B \\sim C23: within 2A with sigma of 0.004 and sigma for terminal atoms of
0.008
5. Others
 Fixed Sof: F1(0.33333) F1A(0.33333) F1B(0.33333) F2(0.33333) F2A(0.33333)
 F2B(0.33333) F3(0.33333) F3A(0.33333) F3B(0.33333)
6.a Ternary CH refined with riding coordinates:
 C2(H2)
6.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C13(H13A,H13B), C21(H21A,H21B)
6.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C8(H8), C9(H9), C17(H17), C18(H18), C19(H19), C25(H25),
 C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
6.d X=CH2 refined with riding coordinates:
 C24(H24A,H24B)
6.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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
F1 F 0.3565(12) 0.8057(8) -0.0383(6) 0.102(2) Uani 0.3333 1 d D U P A 1
F1A F 0.3032(11) 0.8135(3) -0.0094(6) 0.088(3) Uani 0.3333 1 d D U P A 2
F1B F 0.2816(12) 0.8168(5) 0.0028(8) 0.092(3) Uani 0.3333 1 d D U P A 3
F2 F 0.2878(10) 0.8370(7) 0.0715(8) 0.105(2) Uani 0.3333 1 d D U P A 1
F2A F 0.3485(10) 0.8428(7) 0.0998(6) 0.074(2) Uani 0.3333 1 d D U P A 2
F2B F 0.4012(11) 0.8492(9) 0.1014(7) 0.084(2) Uani 0.3333 1 d D U P A 3
F3 F 0.4796(11) 0.8554(9) 0.0363(9) 0.087(2) Uani 0.3333 1 d D U P A 1
F3A F 0.4960(11) 0.8341(11) 0.0155(7) 0.084(3) Uani 0.3333 1 d D U P A 2
F3B F 0.4669(11) 0.8358(11) -0.0081(7) 0.097(3) Uani 0.3333 1 d D U P A 3
O1 O 0.4073(2) 0.16908(18) 0.24199(14) 0.0512(6) Uani 1 1 d . . . . .
O2 O 0.6060(2) 0.2523(2) 0.02955(14) 0.0589(7) Uani 1 1 d . . . . .
O3 O 0.2572(3) 0.4239(2) 0.41599(15) 0.0673(8) Uani 1 1 d . . . . .
O4 O 0.4516(2) 0.3121(2) -0.03495(14) 0.0566(7) Uani 1 1 d . . . . .
O5 O 0.3480(3) 0.5609(2) 0.35618(15) 0.0632(7) Uani 1 1 d . . . . .
C1 C 0.4521(3) 0.3521(2) 0.23176(17) 0.0385(7) Uani 1 1 d . . . . .
C2 C 0.5250(3) 0.3293(2) 0.16357(18) 0.0393(7) Uani 1 1 d . . . . .
H2 H 0.5440 0.2546 0.1649 0.047 Uiso 1 1 calc R . . . .
C3 C 0.5141(3) 0.2978(3) 0.02698(19) 0.0427(7) Uani 1 1 d . . . . .
C4 C 0.4418(3) 0.4538(3) 0.25939(18) 0.0424(7) Uani 1 1 d . . . . .
H4 H 0.4795 0.5098 0.2366 0.051 Uiso 1 1 calc R . . . .
C5 C 0.3744(3) 0.4679(3) 0.32103(18) 0.0444(7) Uani 1 1 d . . . . .
C6 C 0.3943(3) 0.2706(2) 0.26742(19) 0.0430(7) Uani 1 1 d . . . . .
C7 C 0.3338(3) 0.5194(3) 0.1031(2) 0.0479(8) Uani 1 1 d . . . . .
H7 H 0.2761 0.4840 0.1300 0.057 Uiso 1 1 calc R . . . .
C8 C 0.3259(3) 0.2863(3) 0.3308(2) 0.0500(8) Uani 1 1 d . . . . .
H8 H 0.2876 0.2314 0.3545 0.060 Uiso 1 1 calc R . . . .
C9 C 0.6420(3) 0.3868(3) 0.1660(2) 0.0490(8) Uani 1 1 d . . . . .
H9 H 0.6491 0.4455 0.1361 0.059 Uiso 1 1 calc R . . . .
C10 C 0.3268(3) 0.2916(2) 0.09913(19) 0.0396(7) Uani 1 1 d . . . . .
H10A H 0.2826 0.3239 0.1389 0.048 Uiso 1 1 calc R . . . .
H10B H 0.2821 0.3031 0.0543 0.048 Uiso 1 1 calc R . . . .
C11 C 0.3187(3) 0.3867(3) 0.35602(18) 0.0491(8) Uani 1 1 d . . . . .
C12 C 0.3331(3) 0.1746(2) 0.1133(2) 0.0478(8) Uani 1 1 d . . . . .
C13 C 0.3178(4) 0.1357(3) 0.1901(2) 0.0543(9) Uani 1 1 d . . . . .
H13A H 0.2406 0.1584 0.2078 0.065 Uiso 1 1 calc R . . . .
H13B H 0.3172 0.0599 0.1890 0.065 Uiso 1 1 calc R . . . .
C14 C 0.4308(3) 0.4651(2) 0.07624(17) 0.0388(7) Uani 1 1 d . . . . .
C15 C 0.4042(4) 0.6792(3) 0.0505(2) 0.0549(9) Uani 1 1 d . . . . .
C16 C 0.8450(4) 0.4180(4) 0.2150(3) 0.0657(11) Uani 1 1 d . . . . .
C17 C 0.5141(3) 0.5208(3) 0.0355(2) 0.0505(8) Uani 1 1 d . . . . .
H17 H 0.5800 0.4862 0.0163 0.061 Uiso 1 1 calc R . . . .
C18 C 0.5005(4) 0.6264(3) 0.0231(2) 0.0604(10) Uani 1 1 d . . . . .
H18 H 0.5573 0.6622 -0.0043 0.073 Uiso 1 1 calc R . . . .
C19 C 0.3207(4) 0.6258(3) 0.0907(2) 0.0564(9) Uani 1 1 d . . . . .
H19 H 0.2552 0.6610 0.1098 0.068 Uiso 1 1 calc R . . . .
C20 C 0.4490(3) 0.3480(2) 0.09202(17) 0.0356(6) Uani 1 1 d . . . . .
C21 C 0.2950(4) 0.5298(4) 0.4237(2) 0.0682(11) Uani 1 1 d . . . . .
H21A H 0.2274 0.5742 0.4349 0.082 Uiso 1 1 calc R . . . .
H21B H 0.3523 0.5357 0.4633 0.082 Uiso 1 1 calc R . . . .
C22 C 0.5029(5) 0.2701(5) -0.1013(2) 0.0766(13) Uani 1 1 d . . . . .
H22A H 0.4498 0.2824 -0.1417 0.115 Uiso 1 1 calc GR . . . .
H22B H 0.5151 0.1963 -0.0957 0.115 Uiso 1 1 calc GR . . . .
H22C H 0.5778 0.3036 -0.1108 0.115 Uiso 1 1 calc GR . . . .
C23 C 0.3866(4) 0.7914(3) 0.0371(3) 0.0819(13) Uani 1 1 d D U . . .
C24 C 0.3411(5) 0.1077(3) 0.0585(3) 0.0707(12) Uani 1 1 d . . . . .
H24A H 0.3371 0.0362 0.0676 0.085 Uiso 1 1 calc R . . . .
H24B H 0.3506 0.1319 0.0108 0.085 Uiso 1 1 calc R . . . .
C25 C 0.7302(4) 0.3634(4) 0.2041(3) 0.0795(15) Uani 1 1 d . . . . .
H25 H 0.7225 0.3012 0.2301 0.095 Uiso 1 1 calc R . . . .
C26 C 0.9183(5) 0.3904(7) 0.2725(4) 0.113(2) Uani 1 1 d . . . . .
H26 H 0.8962 0.3365 0.3039 0.136 Uiso 1 1 calc R . . . .
C27 C 0.8817(4) 0.4973(4) 0.1701(3) 0.0750(13) Uani 1 1 d . . . . .
H27 H 0.8335 0.5181 0.1312 0.090 Uiso 1 1 calc R . . . .
C28 C 1.0250(5) 0.4428(9) 0.2835(5) 0.133(3) Uani 1 1 d . . . . .
H28 H 1.0728 0.4244 0.3232 0.160 Uiso 1 1 calc R . . . .
C29 C 1.0606(5) 0.5189(8) 0.2387(4) 0.121(3) Uani 1 1 d . . . . .
H29 H 1.1332 0.5521 0.2463 0.146 Uiso 1 1 calc R . . . .
C30 C 0.9894(5) 0.5474(6) 0.1817(4) 0.114(2) Uani 1 1 d . . . . .
H30 H 1.0133 0.6007 0.1503 0.136 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
F1 C23 1.425(10) . ?
F1A C23 1.293(6) . ?
F1B C23 1.373(9) . ?
F2 C23 1.401(10) . ?
F2A C23 1.386(10) . ?
F2B C23 1.395(10) . ?
F3 C23 1.327(11) . ?
F3A C23 1.401(11) . ?
F3B C23 1.346(10) . ?
O1 C6 1.386(4) . ?
O1 C13 1.444(4) . ?
O2 C3 1.186(4) . ?
O3 C11 1.378(4) . ?
O3 C21 1.427(5) . ?
O4 C3 1.341(4) . ?
O4 C22 1.443(5) . ?
O5 C5 1.383(4) . ?
O5 C21 1.423(5) . ?
C1 C2 1.516(4) . ?
C1 C4 1.400(5) . ?
C1 C6 1.390(5) . ?
C2 C9 1.506(5) . ?
C2 C20 1.576(4) . ?
C3 C20 1.533(4) . ?
C4 C5 1.366(5) . ?
C5 C11 1.371(5) . ?
C6 C8 1.402(5) . ?
C7 C14 1.381(5) . ?
C7 C19 1.387(5) . ?
C8 C11 1.366(5) . ?
C9 C25 1.246(6) . ?
C10 C12 1.522(4) . ?
C10 C20 1.555(4) . ?
C12 C13 1.494(5) . ?
C12 C24 1.318(5) . ?
C14 C17 1.390(5) . ?
C14 C20 1.539(4) . ?
C15 C18 1.370(6) . ?
C15 C19 1.371(6) . ?
C15 C23 1.470(5) . ?
C16 C25 1.479(6) . ?
C16 C26 1.378(7) . ?
C16 C27 1.367(7) . ?
C17 C18 1.379(5) . ?
C26 C28 1.388(10) . ?
C27 C30 1.384(7) . ?
C28 C29 1.332(12) . ?
C29 C30 1.361(10) . ?

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 O1 C13 115.0(3) . . ?
C11 O3 C21 104.9(3) . . ?
C3 O4 C22 116.5(3) . . ?
C5 O5 C21 104.4(3) . . ?
C4 C1 C2 121.2(3) . . ?
C6 C1 C2 119.4(3) . . ?
C6 C1 C4 119.4(3) . . ?
C1 C2 C20 110.9(2) . . ?
C9 C2 C1 110.7(3) . . ?
C9 C2 C20 115.0(3) . . ?
O2 C3 O4 123.7(3) . . ?
O2 C3 C20 126.2(3) . . ?
O4 C3 C20 110.1(3) . . ?
C5 C4 C1 117.7(3) . . ?
C4 C5 O5 127.8(3) . . ?
C4 C5 C11 122.3(3) . . ?
C11 C5 O5 109.8(3) . . ?
O1 C6 C1 119.9(3) . . ?
O1 C6 C8 117.9(3) . . ?
C1 C6 C8 122.2(3) . . ?
C14 C7 C19 121.3(3) . . ?
C11 C8 C6 116.4(3) . . ?
C25 C9 C2 126.3(4) . . ?
C12 C10 C20 115.4(3) . . ?
C5 C11 O3 109.6(3) . . ?
C8 C11 O3 128.4(3) . . ?
C8 C11 C5 122.0(3) . . ?
C13 C12 C10 118.8(3) . . ?
C24 C12 C10 120.9(4) . . ?
C24 C12 C13 120.0(3) . . ?
O1 C13 C12 115.8(3) . . ?
C7 C14 C17 117.5(3) . . ?
C7 C14 C20 121.9(3) . . ?
C17 C14 C20 120.6(3) . . ?
C18 C15 C19 119.2(3) . . ?
C18 C15 C23 121.8(4) . . ?
C19 C15 C23 119.0(4) . . ?
C26 C16 C25 120.1(5) . . ?
C27 C16 C25 122.2(4) . . ?
C27 C16 C26 117.7(5) . . ?
C18 C17 C14 121.1(3) . . ?
C15 C18 C17 120.7(4) . . ?
C15 C19 C7 120.2(4) . . ?
C3 C20 C2 108.5(2) . . ?
C3 C20 C10 106.9(2) . . ?
C3 C20 C14 109.1(2) . . ?
C10 C20 C2 109.8(2) . . ?
C14 C20 C2 111.9(2) . . ?
C14 C20 C10 110.5(2) . . ?
O5 C21 O3 107.8(3) . . ?
F1 C23 C15 108.6(5) . . ?
F1A C23 F2A 102.2(9) . . ?
F1A C23 F3A 111.5(9) . . ?
F1A C23 C15 114.8(4) . . ?
F1B C23 F2B 110.9(8) . . ?
F1B C23 C15 115.0(4) . . ?
F2 C23 F1 100.9(8) . . ?
F2 C23 C15 116.0(6) . . ?
F2A C23 F3A 108.5(8) . . ?
F2A C23 C15 111.5(6) . . ?
F2B C23 C15 111.2(6) . . ?
F3 C23 F1 95.6(9) . . ?
F3 C23 F2 111.7(8) . . ?
F3 C23 C15 120.0(7) . . ?
F3A C23 C15 108.1(7) . . ?
F3B C23 F1B 101.4(9) . . ?
F3B C23 F2B 102.2(9) . . ?
F3B C23 C15 115.1(7) . . ?
C9 C25 C16 130.8(4) . . ?
C16 C26 C28 120.1(7) . . ?
C16 C27 C30 121.1(6) . . ?
C29 C28 C26 121.5(7) . . ?
C28 C29 C30 119.2(6) . . ?
C29 C30 C27 120.3(7) . . ?

_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 1.624
_oxdiff_exptl_absorpt_empirical_full_min 0.842
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate/petroleum ether'
####################################################################### 
# 
# 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_210202e
_database_code_depnum_ccdc_archive 'CCDC 2106767'
loop_
_audit_author_name
_audit_author_address
'Xiaoxun Li'
;Shandong University
China
;
_audit_update_record             
;
2021-09-01 deposited with the CCDC.	2022-05-16 downloaded from the CCDC.
;
_audit_creation_date             2021-02-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        3an
_chemical_formula_moiety         'C29 H23 Cl2 O5'
_chemical_formula_sum            'C29 H23 Cl2 O5'
_chemical_formula_weight         522.37
_chemical_absolute_configuration syn
_chemical_melting_point          466-468
_chemical_oxdiff_formula         ClC
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'
Cl Cl 0.3639 0.7018 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   11.4261(6)
_cell_length_b                   12.5763(7)
_cell_length_c                   17.9861(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2584.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3906
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.9060
_cell_measurement_theta_min      4.5530
_shelx_estimated_absorpt_T_max   0.882
_shelx_estimated_absorpt_T_min   0.861
_exptl_absorpt_coefficient_mu    2.573
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1084
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0786
_diffrn_reflns_av_unetI/netI     0.0864
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12224
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.048
_diffrn_reflns_theta_min         4.585
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.975
_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    109.00 177.00   1.00    2.00    --  106.49  38.00 -60.00   68
  2  ω     92.00 178.00   1.00    2.00    --  106.49  57.00 -30.00   86
  3  ω    101.00 129.00   1.00    2.00    --  106.49  84.00 151.00   28
  4  ω    134.00 168.00   1.00    2.00    --  106.49  84.00 151.00   34
  5  ω    -26.00  27.00   1.00    0.12    --   48.45 -19.00  90.00   53
  6  ω     34.00  66.00   1.00    2.00    --  106.49 -57.00 150.00   32
  7  ω     34.00 130.00   1.00    2.00    --  106.49 -80.00 139.00   96
  8  ω     34.00  66.00   1.00    2.00    --  106.49 -57.00 -30.00   32
  9  ω     34.00  66.00   1.00    2.00    --  106.49 -57.00-150.00   32
 10  ω   -120.00 -74.00   1.00    0.12    --  -48.45-125.00-180.00   46
 11  ω   -159.00 -79.00   1.00    2.00    --  -86.25 -59.00-100.00   80
 12  ω    -42.00 -15.00   1.00    2.00    --  -86.25  38.00-120.00   27
 13  ω    -43.00 -14.00   1.00    2.00    --  -86.25  38.00   0.00   29
 14  ω    -72.00   5.00   1.00    0.12    --  -48.45  84.00 151.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0775483000
_diffrn_orient_matrix_UB_12      0.0049901000
_diffrn_orient_matrix_UB_13      0.0700290000
_diffrn_orient_matrix_UB_21      0.0488063000
_diffrn_orient_matrix_UB_22      -0.1081990000
_diffrn_orient_matrix_UB_23      0.0255370000
_diffrn_orient_matrix_UB_31      0.0990186000
_diffrn_orient_matrix_UB_32      0.0571380000
_diffrn_orient_matrix_UB_33      0.0420514000
_diffrn_oxdiff_digest_frames     
;
017584e7fef3ebed31e79c0728a7637dbf00720b503
;
_diffrn_oxdiff_digest_hkl        
;
013e9b8adffc483a0d046a9b7f6be3ac1faa5b
;
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    0.953
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3729
_reflns_number_total             4520
_reflns_odcompleteness_completeness 98.86
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 1348 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_coef       0.0042(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4520
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0647
_refine_ls_restrained_S_all      1.100
_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)+(0.0891P)²+0.6992P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1728
_refine_ls_wR_factor_ref         0.1832
_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. Restrained distances
 C20-Cl1
 1.7 with sigma of 0.01
3. Others
 Fixed Sof: Cl1(0.5) Cl1A(0.5) Cl2(0.4) Cl2A(0.6)
4.a Ternary CH refined with riding coordinates:
 C4(H4)
4.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C11(H11A,H11B), C17(H17A,H17B)
4.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C13(H13), C15(H15), C19(H19), C21(H21), C23(H23), C26(H26),
 C27(H27), C28(H28), C29(H29)
4.d Fitted hexagon refined as free rotating group:
 C20(C21,C22,C23,C24,C25)
4.e X=CH2 refined with riding coordinates:
 C16(H16A,H16B)
4.f Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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
Cl1 Cl 0.4008(5) 0.6940(4) 0.5224(3) 0.1167(15) Uani 0.5 1 d D . P A 2
Cl1A Cl 0.7486(5) 0.7106(3) 0.3792(3) 0.1183(18) Uani 0.5 1 d . . P A 1
Cl2 Cl 0.6129(9) 0.8167(4) 0.4462(6) 0.125(2) Uani 0.4 1 d . . P A 2
Cl2A Cl 0.5573(5) 0.8141(3) 0.4831(3) 0.0998(12) Uani 0.6 1 d . . P A 1
O1 O 0.5954(3) 0.1597(3) 0.2585(2) 0.0562(9) Uani 1 1 d . . . . .
O2 O 0.3904(4) 0.2443(3) 0.4691(2) 0.0655(10) Uani 1 1 d . . . . .
O3 O 0.5403(3) 0.3060(3) 0.5356(2) 0.0647(10) Uani 1 1 d . . . . .
O4 O 0.6555(4) 0.5544(3) 0.1390(2) 0.0754(12) Uani 1 1 d . . . . .
O5 O 0.7497(4) 0.4141(4) 0.0820(2) 0.0784(12) Uani 1 1 d . . . . .
C1 C 0.5476(4) 0.3449(4) 0.2650(3) 0.0454(10) Uani 1 1 d . . . . .
C2 C 0.5450(4) 0.3436(3) 0.4071(3) 0.0452(10) Uani 1 1 d . . . . .
C3 C 0.6283(5) 0.4603(4) 0.1748(3) 0.0529(11) Uani 1 1 d . . . . .
C4 C 0.4739(4) 0.3239(4) 0.3336(3) 0.0450(10) Uani 1 1 d . . . . .
H4 H 0.4540 0.2481 0.3327 0.054 Uiso 1 1 calc R . . . .
C5 C 0.6680(4) 0.2896(4) 0.4018(3) 0.0491(11) Uani 1 1 d . . . . .
H5A H 0.7112 0.3229 0.3616 0.059 Uiso 1 1 calc R . . . .
H5B H 0.7102 0.3036 0.4475 0.059 Uiso 1 1 calc R . . . .
C6 C 0.6073(4) 0.2615(4) 0.2311(3) 0.0466(10) Uani 1 1 d . . . . .
C7 C 0.6668(5) 0.1704(4) 0.3887(3) 0.0548(12) Uani 1 1 d . . . . .
C8 C 0.4812(4) 0.2911(4) 0.4719(3) 0.0498(11) Uani 1 1 d . . . . .
C9 C 0.5582(4) 0.4472(4) 0.2354(3) 0.0511(11) Uani 1 1 d . . . . .
H9 H 0.5188 0.5045 0.2565 0.061 Uiso 1 1 calc R . . . .
C10 C 0.6854(5) 0.3780(4) 0.1419(3) 0.0555(12) Uani 1 1 d . . . . .
C11 C 0.6836(5) 0.1279(4) 0.3118(3) 0.0592(13) Uani 1 1 d . . . . .
H11A H 0.7594 0.1511 0.2937 0.071 Uiso 1 1 calc R . . . .
H11B H 0.6849 0.0509 0.3142 0.071 Uiso 1 1 calc R . . . .
C12 C 0.6781(5) 0.2768(4) 0.1684(3) 0.0570(12) Uani 1 1 d . . . . .
H12 H 0.7179 0.2208 0.1460 0.068 Uiso 1 1 calc R . . . .
C13 C 0.3596(4) 0.3839(5) 0.3294(3) 0.0556(12) Uani 1 1 d . . . . .
H13 H 0.3596 0.4509 0.3513 0.067 Uiso 1 1 calc R . . . .
C14 C 0.1558(5) 0.4164(6) 0.2898(4) 0.0704(15) Uani 1 1 d . . . . .
C15 C 0.2651(6) 0.3558(6) 0.3006(5) 0.083(2) Uani 1 1 d . . . . .
H15 H 0.2633 0.2861 0.2834 0.099 Uiso 1 1 calc R . . . .
C16 C 0.6605(6) 0.1022(5) 0.4447(4) 0.0796(18) Uani 1 1 d . . . . .
H16A H 0.6665 0.0296 0.4357 0.096 Uiso 1 1 calc R . . . .
H16B H 0.6502 0.1270 0.4929 0.096 Uiso 1 1 calc R . . . .
C17 C 0.7124(7) 0.5222(6) 0.0726(4) 0.0807(19) Uani 1 1 d . . . . .
H17A H 0.7794 0.5675 0.0629 0.097 Uiso 1 1 calc R . . . .
H17B H 0.6591 0.5276 0.0308 0.097 Uiso 1 1 calc R . . . .
C18 C 0.4865(7) 0.2653(7) 0.6021(3) 0.085(2) Uani 1 1 d . . . . .
H18A H 0.4751 0.1900 0.5973 0.127 Uiso 1 1 calc GR . . . .
H18B H 0.4123 0.2994 0.6095 0.127 Uiso 1 1 calc GR . . . .
H18C H 0.5363 0.2794 0.6440 0.127 Uiso 1 1 calc GR . . . .
C19 C 0.1255(5) 0.5006(5) 0.3342(4) 0.0727(16) Uani 1 1 d . . . . .
H19 H 0.1755 0.5222 0.3721 0.087 Uiso 1 1 calc R . . . .
C20 C 0.4781(5) 0.6210(3) 0.4805(3) 0.103(3) Uani 1 1 d D . . . .
C21 C 0.4718(3) 0.5124(3) 0.4668(2) 0.0753(17) Uani 1 1 d G . . A .
H21 H 0.4104 0.4727 0.4864 0.090 Uiso 1 1 calc R . . . .
C22 C 0.5571(3) 0.4632(2) 0.4239(2) 0.0560(12) Uani 1 1 d G . . A .
C23 C 0.6488(3) 0.5225(3) 0.3946(2) 0.0727(17) Uani 1 1 d G . . A .
H23 H 0.7059 0.4896 0.3659 0.087 Uiso 1 1 calc R . . . .
C24 C 0.6551(5) 0.6312(3) 0.4083(3) 0.100(3) Uani 1 1 d G . . A .
C25 C 0.5697(6) 0.6804(2) 0.4513(3) 0.112(3) Uani 1 1 d G . . A .
C26 C -0.0533(7) 0.5227(10) 0.2673(6) 0.111(3) Uani 1 1 d . . . . .
H26 H -0.1231 0.5591 0.2598 0.134 Uiso 1 1 calc R . . . .
C27 C 0.0215(7) 0.5532(8) 0.3229(6) 0.104(3) Uani 1 1 d . . . . .
H27 H 0.0016 0.6101 0.3534 0.124 Uiso 1 1 calc R . . . .
C28 C -0.0251(8) 0.4398(11) 0.2235(6) 0.126(4) Uani 1 1 d . . . . .
H28 H -0.0757 0.4188 0.1858 0.151 Uiso 1 1 calc R . . . .
C29 C 0.0780(6) 0.3863(8) 0.2344(6) 0.105(3) Uani 1 1 d . . . . .
H29 H 0.0962 0.3288 0.2040 0.126 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
Cl1 C20 1.479(5) . ?
Cl1A C24 1.554(5) . ?
Cl2 C25 1.787(7) . ?
Cl2A C25 1.782(4) . ?
O1 C6 1.378(6) . ?
O1 C11 1.447(7) . ?
O2 C8 1.194(6) . ?
O3 C8 1.342(6) . ?
O3 C18 1.440(8) . ?
O4 C3 1.382(6) . ?
O4 C17 1.419(8) . ?
O5 C10 1.380(7) . ?
O5 C17 1.434(8) . ?
C1 C4 1.517(7) . ?
C1 C6 1.392(7) . ?
C1 C9 1.398(7) . ?
C2 C4 1.572(6) . ?
C2 C5 1.564(7) . ?
C2 C8 1.525(7) . ?
C2 C22 1.539(5) . ?
C3 C9 1.363(7) . ?
C3 C10 1.360(8) . ?
C4 H4 0.9800 . ?
C4 C13 1.509(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C7 1.517(7) . ?
C6 C12 1.402(7) . ?
C7 C11 1.496(8) . ?
C7 C16 1.324(8) . ?
C9 H9 0.9300 . ?
C10 C12 1.361(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C15 1.249(8) . ?
C14 C15 1.475(9) . ?
C14 C19 1.370(10) . ?
C14 C29 1.389(10) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9300 . ?
C16 H16B 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19 0.9300 . ?
C19 C27 1.375(10) . ?
C20 C21 1.3900 . ?
C20 C25 1.3900 . ?
C21 H21 0.9300 . ?
C21 C22 1.3900 . ?
C22 C23 1.3900 . ?
C23 H23 0.9300 . ?
C23 C24 1.3900 . ?
C24 C25 1.3900 . ?
C26 H26 0.9300 . ?
C26 C27 1.371(14) . ?
C26 C28 1.345(16) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C28 C29 1.371(13) . ?
C29 H29 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
C6 O1 C11 115.1(4) . . ?
C8 O3 C18 116.4(5) . . ?
C3 O4 C17 104.6(4) . . ?
C10 O5 C17 104.3(4) . . ?
C6 C1 C4 119.8(4) . . ?
C6 C1 C9 119.0(4) . . ?
C9 C1 C4 121.2(4) . . ?
C5 C2 C4 110.1(4) . . ?
C8 C2 C4 109.1(4) . . ?
C8 C2 C5 106.8(4) . . ?
C8 C2 C22 108.4(4) . . ?
C22 C2 C4 111.4(3) . . ?
C22 C2 C5 110.8(3) . . ?
C9 C3 O4 127.5(5) . . ?
C10 C3 O4 109.9(4) . . ?
C10 C3 C9 122.6(5) . . ?
C1 C4 C2 111.7(3) . . ?
C1 C4 H4 106.6 . . ?
C2 C4 H4 106.6 . . ?
C13 C4 C1 110.7(4) . . ?
C13 C4 C2 114.2(4) . . ?
C13 C4 H4 106.6 . . ?
C2 C5 H5A 108.4 . . ?
C2 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
C7 C5 C2 115.5(4) . . ?
C7 C5 H5A 108.4 . . ?
C7 C5 H5B 108.4 . . ?
O1 C6 C1 119.7(4) . . ?
O1 C6 C12 118.2(4) . . ?
C1 C6 C12 122.1(4) . . ?
C11 C7 C5 119.7(4) . . ?
C16 C7 C5 121.5(5) . . ?
C16 C7 C11 118.6(5) . . ?
O2 C8 O3 122.8(5) . . ?
O2 C8 C2 126.6(5) . . ?
O3 C8 C2 110.5(4) . . ?
C1 C9 H9 121.1 . . ?
C3 C9 C1 117.8(5) . . ?
C3 C9 H9 121.1 . . ?
C3 C10 O5 110.1(5) . . ?
C3 C10 C12 122.0(5) . . ?
C12 C10 O5 127.9(5) . . ?
O1 C11 C7 115.2(4) . . ?
O1 C11 H11A 108.5 . . ?
O1 C11 H11B 108.5 . . ?
C7 C11 H11A 108.5 . . ?
C7 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C6 C12 H12 121.7 . . ?
C10 C12 C6 116.5(5) . . ?
C10 C12 H12 121.7 . . ?
C4 C13 H13 115.6 . . ?
C15 C13 C4 128.8(5) . . ?
C15 C13 H13 115.6 . . ?
C19 C14 C15 122.5(6) . . ?
C19 C14 C29 117.8(6) . . ?
C29 C14 C15 119.7(7) . . ?
C13 C15 C14 129.8(6) . . ?
C13 C15 H15 115.1 . . ?
C14 C15 H15 115.1 . . ?
C7 C16 H16A 120.0 . . ?
C7 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?
O4 C17 O5 107.8(5) . . ?
O4 C17 H17A 110.1 . . ?
O4 C17 H17B 110.1 . . ?
O5 C17 H17A 110.1 . . ?
O5 C17 H17B 110.1 . . ?
H17A C17 H17B 108.5 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19 119.8 . . ?
C14 C19 C27 120.4(7) . . ?
C27 C19 H19 119.8 . . ?
C21 C20 Cl1 132.0(4) . . ?
C21 C20 C25 120.0 . . ?
C25 C20 Cl1 108.0(4) . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C2 118.7(3) . . ?
C21 C22 C23 120.0 . . ?
C23 C22 C2 121.2(3) . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 Cl1A 127.4(4) . . ?
C25 C24 Cl1A 112.5(4) . . ?
C25 C24 C23 120.0 . . ?
C20 C25 Cl2 138.0(5) . . ?
C20 C25 Cl2A 109.0(4) . . ?
C24 C25 Cl2 101.8(5) . . ?
C24 C25 Cl2A 130.9(4) . . ?
C24 C25 C20 120.0 . . ?
C27 C26 H26 120.1 . . ?
C28 C26 H26 120.1 . . ?
C28 C26 C27 119.7(7) . . ?
C19 C27 H27 119.6 . . ?
C26 C27 C19 120.7(9) . . ?
C26 C27 H27 119.6 . . ?
C26 C28 H28 119.9 . . ?
C26 C28 C29 120.2(9) . . ?
C29 C28 H28 119.9 . . ?
C14 C29 H29 119.4 . . ?
C28 C29 C14 121.3(9) . . ?
C28 C29 H29 119.4 . . ?

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
Cl1 C20 C21 C22 179.0(5) . . . . ?
Cl1 C20 C25 Cl2 -4.6(6) . . . . ?
Cl1 C20 C25 Cl2A 4.1(4) . . . . ?
Cl1 C20 C25 C24 -179.2(4) . . . . ?
Cl1A C24 C25 Cl2 2.4(5) . . . . ?
Cl1A C24 C25 Cl2A -5.4(5) . . . . ?
Cl1A C24 C25 C20 178.7(4) . . . . ?
O1 C6 C12 C10 178.4(5) . . . . ?
O4 C3 C9 C1 -176.7(5) . . . . ?
O4 C3 C10 O5 -1.7(6) . . . . ?
O4 C3 C10 C12 177.0(5) . . . . ?
O5 C10 C12 C6 179.1(5) . . . . ?
C1 C4 C13 C15 87.7(8) . . . . ?
C1 C6 C12 C10 -0.1(7) . . . . ?
C2 C4 C13 C15 -145.2(7) . . . . ?
C2 C5 C7 C11 98.3(6) . . . . ?
C2 C5 C7 C16 -87.1(7) . . . . ?
C2 C22 C23 C24 177.5(4) . . . . ?
C3 O4 C17 O5 -18.0(7) . . . . ?
C3 C10 C12 C6 0.7(8) . . . . ?
C4 C1 C6 O1 2.5(6) . . . . ?
C4 C1 C6 C12 -179.0(4) . . . . ?
C4 C1 C9 C3 178.5(4) . . . . ?
C4 C2 C5 C7 -58.8(5) . . . . ?
C4 C2 C8 O2 -1.6(7) . . . . ?
C4 C2 C8 O3 179.6(4) . . . . ?
C4 C2 C22 C21 90.0(4) . . . . ?
C4 C2 C22 C23 -87.6(4) . . . . ?
C4 C13 C15 C14 -173.7(7) . . . . ?
C5 C2 C4 C1 -46.5(5) . . . . ?
C5 C2 C4 C13 -173.0(4) . . . . ?
C5 C2 C8 O2 -120.6(5) . . . . ?
C5 C2 C8 O3 60.6(5) . . . . ?
C5 C2 C22 C21 -147.0(3) . . . . ?
C5 C2 C22 C23 35.4(5) . . . . ?
C5 C7 C11 O1 -61.5(7) . . . . ?
C6 O1 C11 C7 78.0(6) . . . . ?
C6 C1 C4 C2 93.5(5) . . . . ?
C6 C1 C4 C13 -138.0(4) . . . . ?
C6 C1 C9 C3 -0.7(7) . . . . ?
C8 C2 C4 C1 -163.4(4) . . . . ?
C8 C2 C4 C13 70.1(5) . . . . ?
C8 C2 C5 C7 59.6(5) . . . . ?
C8 C2 C22 C21 -30.1(5) . . . . ?
C8 C2 C22 C23 152.3(3) . . . . ?
C9 C1 C4 C2 -85.6(5) . . . . ?
C9 C1 C4 C13 42.8(6) . . . . ?
C9 C1 C6 O1 -178.3(4) . . . . ?
C9 C1 C6 C12 0.1(7) . . . . ?
C9 C3 C10 O5 -179.9(5) . . . . ?
C9 C3 C10 C12 -1.3(8) . . . . ?
C10 O5 C17 O4 17.0(7) . . . . ?
C10 C3 C9 C1 1.2(8) . . . . ?
C11 O1 C6 C1 -93.6(5) . . . . ?
C11 O1 C6 C12 87.9(5) . . . . ?
C14 C19 C27 C26 -0.2(13) . . . . ?
C15 C14 C19 C27 -178.6(8) . . . . ?
C15 C14 C29 C28 179.0(10) . . . . ?
C16 C7 C11 O1 123.7(6) . . . . ?
C17 O4 C3 C9 -169.6(6) . . . . ?
C17 O4 C3 C10 12.2(6) . . . . ?
C17 O5 C10 C3 -9.5(7) . . . . ?
C17 O5 C10 C12 171.9(6) . . . . ?
C18 O3 C8 O2 -2.1(8) . . . . ?
C18 O3 C8 C2 176.8(5) . . . . ?
C19 C14 C15 C13 -25.6(13) . . . . ?
C19 C14 C29 C28 0.9(14) . . . . ?
C20 C21 C22 C2 -177.6(4) . . . . ?
C20 C21 C22 C23 0.0 . . . . ?
C21 C20 C25 Cl2 174.6(6) . . . . ?
C21 C20 C25 Cl2A -176.7(4) . . . . ?
C21 C20 C25 C24 0.0 . . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C22 C2 C4 C1 76.9(5) . . . . ?
C22 C2 C4 C13 -49.6(5) . . . . ?
C22 C2 C5 C7 177.4(4) . . . . ?
C22 C2 C8 O2 119.9(5) . . . . ?
C22 C2 C8 O3 -58.9(5) . . . . ?
C22 C23 C24 Cl1A -178.5(5) . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C23 C24 C25 Cl2 -176.3(4) . . . . ?
C23 C24 C25 Cl2A 175.9(5) . . . . ?
C23 C24 C25 C20 0.0 . . . . ?
C25 C20 C21 C22 0.0 . . . . ?
C26 C28 C29 C14 -0.6(17) . . . . ?
C27 C26 C28 C29 -0.2(17) . . . . ?
C28 C26 C27 C19 0.5(15) . . . . ?
C29 C14 C15 C13 156.4(9) . . . . ?
C29 C14 C19 C27 -0.5(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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.357
_oxdiff_exptl_absorpt_empirical_full_min 0.329
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate/petroleum ether'
