# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_201709178
_database_code_depnum_ccdc_archive 'CCDC 1858969'
loop_
_audit_author_name
_audit_author_address
'QingRui Li'
;University
China
;
_audit_update_record             
;
2018-07-29 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;
_audit_creation_date             2017-09-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 O6'
_chemical_formula_sum            'C23 H20 O6'
_chemical_formula_weight         392.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         C38H41N2O2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.7957(7)
_cell_length_b                   10.1827(6)
_cell_length_c                   12.7574(8)
_cell_angle_alpha                79.033(5)
_cell_angle_beta                 76.634(7)
_cell_angle_gamma                77.369(6)
_cell_volume                     950.95(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2407
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.4510
_cell_measurement_theta_min      3.6850
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7725
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.319
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   24.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.1755  -99.0000   60.0000 49

#__ type_ start__ end____ width___ exp.time_
  2 omega  -79.00  -30.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.1755  143.0000  -55.0000 49

#__ type_ start__ end____ width___ exp.time_
  3 omega   -6.00   23.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.1755  -99.0000 -120.0000 29

#__ type_ start__ end____ width___ exp.time_
  4 omega  -65.00  -28.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.1755  127.0000  134.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega   10.00   67.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       18.0661   57.0000  -60.0000 57

#__ type_ start__ end____ width___ exp.time_
  6 omega  -27.00   23.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -57.0000   60.0000 50

#__ type_ start__ end____ width___ exp.time_
  7 omega  -49.00   85.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       18.0661    0.0000   90.0000 134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0774889000
_diffrn_orient_matrix_UB_12      -0.0203429000
_diffrn_orient_matrix_UB_13      -0.0070877000
_diffrn_orient_matrix_UB_21      -0.0314515000
_diffrn_orient_matrix_UB_22      -0.0089241000
_diffrn_orient_matrix_UB_23      0.0572265000
_diffrn_orient_matrix_UB_31      -0.0453300000
_diffrn_orient_matrix_UB_32      0.0686671000
_diffrn_orient_matrix_UB_33      -0.0035981000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2604
_reflns_number_total             3885
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3885
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²+0.2099P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1395
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0061(3) 0.5842(2) 0.67992(17) 0.0369(5) Uani 1 1 d . . . . .
C2 C 0.0147(3) 0.72451(18) 0.67851(15) 0.0326(5) Uani 1 1 d . . . . .
C3 C 0.1302(3) 0.79250(19) 0.60339(15) 0.0325(5) Uani 1 1 d . . . . .
C4 C 0.1022(3) 0.93277(19) 0.62776(16) 0.0336(5) Uani 1 1 d . . . . .
C5 C -0.0329(3) 0.94501(19) 0.72131(16) 0.0337(5) Uani 1 1 d . . . . .
C6 C -0.0903(3) 1.0667(2) 0.76255(18) 0.0421(5) Uani 1 1 d . . . . .
H6 H -0.1791 1.0739 0.8250 0.050 Uiso 1 1 calc R . . . .
C7 C -0.0132(3) 1.1778(2) 0.7091(2) 0.0479(6) Uani 1 1 d . . . . .
H7 H -0.0506 1.2604 0.7359 0.057 Uiso 1 1 calc R . . . .
C8 C 0.1188(3) 1.1670(2) 0.61629(19) 0.0481(6) Uani 1 1 d . . . . .
H8 H 0.1687 1.2428 0.5814 0.058 Uiso 1 1 calc R . . . .
C9 C 0.1782(3) 1.0453(2) 0.57424(18) 0.0417(5) Uani 1 1 d . . . . .
H9 H 0.2669 1.0389 0.5116 0.050 Uiso 1 1 calc R . . . .
C10 C 0.2493(3) 0.7257(2) 0.51610(16) 0.0345(5) Uani 1 1 d . . . . .
C11 C 0.2275(3) 0.5935(2) 0.51194(17) 0.0363(5) Uani 1 1 d . . . . .
C12 C 0.3226(3) 0.5225(2) 0.42755(17) 0.0427(5) Uani 1 1 d . . . . .
H12 H 0.3025 0.4363 0.4257 0.051 Uiso 1 1 calc R . . . .
C13 C 0.4472(3) 0.5797(2) 0.34611(17) 0.0449(6) Uani 1 1 d . . . . .
C14 C 0.4757(3) 0.7085(3) 0.35205(19) 0.0517(6) Uani 1 1 d . . . . .
H14 H 0.5622 0.7468 0.2993 0.062 Uiso 1 1 calc R . . . .
C15 C 0.3781(3) 0.7797(2) 0.43439(18) 0.0474(6) Uani 1 1 d . . . . .
H15 H 0.3986 0.8660 0.4356 0.057 Uiso 1 1 calc R . . . .
C16 C -0.1055(3) 0.81225(19) 0.76004(15) 0.0335(5) Uani 1 1 d . . . . .
C17 C -0.0935(3) 0.7470(2) 0.87821(17) 0.0373(5) Uani 1 1 d . . . . .
C18 C -0.3014(3) 0.8390(2) 0.74578(16) 0.0358(5) Uani 1 1 d . . . . .
C19 C 0.1002(4) 0.6687(3) 1.0038(2) 0.0720(9) Uani 1 1 d . . . . .
H19A H 0.0288 0.7236 1.0584 0.086 Uiso 1 1 calc R . . . .
H19B H 0.0619 0.5814 1.0194 0.086 Uiso 1 1 calc R . . . .
C20 C 0.2848(4) 0.6488(4) 1.0095(2) 0.0940(12) Uani 1 1 d . . . . .
H20A H 0.3562 0.5986 0.9529 0.141 Uiso 1 1 calc GR . . . .
H20B H 0.3026 0.5988 1.0791 0.141 Uiso 1 1 calc GR . . . .
H20C H 0.3202 0.7355 1.0002 0.141 Uiso 1 1 calc GR . . . .
C21 C -0.5958(3) 0.9529(2) 0.81054(19) 0.0505(6) Uani 1 1 d . . . . .
H21A H -0.6448 0.8710 0.8185 0.061 Uiso 1 1 calc R . . . .
H21B H -0.6129 1.0076 0.7414 0.061 Uiso 1 1 calc R . . . .
C22 C -0.6865(4) 1.0312(3) 0.9022(2) 0.0818(10) Uani 1 1 d . . . . .
H22A H -0.6396 1.1134 0.8921 0.123 Uiso 1 1 calc GR . . . .
H22B H -0.6652 0.9770 0.9698 0.123 Uiso 1 1 calc GR . . . .
H22C H -0.8132 1.0536 0.9037 0.123 Uiso 1 1 calc GR . . . .
C23 C 0.5486(4) 0.5042(3) 0.25297(19) 0.0621(8) Uani 1 1 d . . . . .
H23A H 0.6120 0.4176 0.2811 0.093 Uiso 1 1 calc GR . . . .
H23B H 0.6327 0.5564 0.2059 0.093 Uiso 1 1 calc GR . . . .
H23C H 0.4658 0.4905 0.2126 0.093 Uiso 1 1 calc GR . . . .
O1 O -0.0809(2) 0.51376(14) 0.74971(12) 0.0516(4) Uani 1 1 d . . . . .
O2 O 0.1103(2) 0.52639(13) 0.59125(11) 0.0425(4) Uani 1 1 d . . . . .
O3 O -0.2148(2) 0.70818(18) 0.94380(13) 0.0612(5) Uani 1 1 d . . . . .
O4 O 0.0705(2) 0.73650(16) 0.89557(12) 0.0528(5) Uani 1 1 d . . . . .
O5 O -0.3513(2) 0.79847(17) 0.67754(13) 0.0546(5) Uani 1 1 d . . . . .
O6 O -0.4062(2) 0.91838(15) 0.81515(12) 0.0468(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 C2 1.441(3) . ?
C1 O1 1.207(2) . ?
C1 O2 1.381(2) . ?
C2 C3 1.352(3) . ?
C2 C16 1.515(3) . ?
C3 C4 1.478(3) . ?
C3 C10 1.449(3) . ?
C4 C5 1.402(3) . ?
C4 C9 1.393(3) . ?
C5 C6 1.382(3) . ?
C5 C16 1.531(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.387(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.388(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.405(3) . ?
C10 C15 1.392(3) . ?
C11 C12 1.387(3) . ?
C11 O2 1.381(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(3) . ?
C13 C14 1.396(4) . ?
C13 C23 1.509(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.374(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.543(3) . ?
C16 C18 1.539(3) . ?
C17 O3 1.193(3) . ?
C17 O4 1.325(3) . ?
C18 O5 1.201(2) . ?
C18 O6 1.324(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.426(4) . ?
C19 O4 1.468(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.493(3) . ?
C21 O6 1.455(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 127.03(19) . . ?
O1 C1 O2 117.75(18) . . ?
O2 C1 C2 115.22(18) . . ?
C1 C2 C16 123.79(18) . . ?
C3 C2 C1 123.53(18) . . ?
C3 C2 C16 112.67(17) . . ?
C2 C3 C4 108.56(17) . . ?
C2 C3 C10 119.96(18) . . ?
C10 C3 C4 131.44(19) . . ?
C5 C4 C3 107.97(18) . . ?
C9 C4 C3 132.23(19) . . ?
C9 C4 C5 119.76(19) . . ?
C4 C5 C16 110.20(17) . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 C16 128.66(19) . . ?
C5 C6 H6 120.6 . . ?
C5 C6 C7 118.8(2) . . ?
C7 C6 H6 120.6 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.2(2) . . ?
C9 C8 H8 119.4 . . ?
C4 C9 H9 120.7 . . ?
C8 C9 C4 118.6(2) . . ?
C8 C9 H9 120.7 . . ?
C11 C10 C3 116.04(19) . . ?
C15 C10 C3 127.14(19) . . ?
C15 C10 C11 116.79(19) . . ?
C12 C11 C10 121.9(2) . . ?
O2 C11 C10 122.20(18) . . ?
O2 C11 C12 115.92(19) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 118.5(2) . . ?
C12 C13 C23 120.4(2) . . ?
C14 C13 C23 121.1(2) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.1(2) . . ?
C15 C14 H14 119.4 . . ?
C10 C15 H15 119.2 . . ?
C14 C15 C10 121.5(2) . . ?
C14 C15 H15 119.2 . . ?
C2 C16 C5 100.51(16) . . ?
C2 C16 C17 111.64(15) . . ?
C2 C16 C18 110.79(17) . . ?
C5 C16 C17 115.26(17) . . ?
C5 C16 C18 108.45(15) . . ?
C18 C16 C17 109.85(17) . . ?
O3 C17 C16 124.2(2) . . ?
O3 C17 O4 124.9(2) . . ?
O4 C17 C16 110.87(18) . . ?
O5 C18 C16 124.49(19) . . ?
O5 C18 O6 124.5(2) . . ?
O6 C18 C16 110.95(17) . . ?
H19A C19 H19B 108.0 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C20 C19 O4 110.9(2) . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
H21A C21 H21B 108.6 . . ?
C22 C21 H21A 110.4 . . ?
C22 C21 H21B 110.4 . . ?
O6 C21 H21A 110.4 . . ?
O6 C21 H21B 110.4 . . ?
O6 C21 C22 106.7(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C13 C23 H23A 109.5 . . ?
C13 C23 H23B 109.5 . . ?
C13 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 O2 C11 122.53(16) . . ?
C17 O4 C19 115.6(2) . . ?
C18 O6 C21 117.00(18) . . ?

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
C1 C2 C3 C4 -179.52(18) . . . . ?
C1 C2 C3 C10 2.3(3) . . . . ?
C1 C2 C16 C5 178.29(18) . . . . ?
C1 C2 C16 C17 55.6(3) . . . . ?
C1 C2 C16 C18 -67.2(2) . . . . ?
C2 C1 O2 C11 5.9(3) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C2 C3 C4 C9 -176.6(2) . . . . ?
C2 C3 C10 C11 4.0(3) . . . . ?
C2 C3 C10 C15 -178.3(2) . . . . ?
C2 C16 C17 O3 -114.7(2) . . . . ?
C2 C16 C17 O4 63.4(2) . . . . ?
C2 C16 C18 O5 -1.6(3) . . . . ?
C2 C16 C18 O6 -178.49(16) . . . . ?
C3 C2 C16 C5 -2.3(2) . . . . ?
C3 C2 C16 C17 -125.07(19) . . . . ?
C3 C2 C16 C18 112.16(19) . . . . ?
C3 C4 C5 C6 -178.80(18) . . . . ?
C3 C4 C5 C16 -2.3(2) . . . . ?
C3 C4 C9 C8 177.9(2) . . . . ?
C3 C10 C11 C12 174.64(18) . . . . ?
C3 C10 C11 O2 -5.2(3) . . . . ?
C3 C10 C15 C14 -176.0(2) . . . . ?
C4 C3 C10 C11 -173.77(19) . . . . ?
C4 C3 C10 C15 4.0(4) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C4 C5 C16 C2 2.8(2) . . . . ?
C4 C5 C16 C17 122.93(18) . . . . ?
C4 C5 C16 C18 -113.48(18) . . . . ?
C5 C4 C9 C8 0.7(3) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C5 C16 C17 O3 131.4(2) . . . . ?
C5 C16 C17 O4 -50.4(2) . . . . ?
C5 C16 C18 O5 107.8(2) . . . . ?
C5 C16 C18 O6 -69.1(2) . . . . ?
C6 C5 C16 C2 178.9(2) . . . . ?
C6 C5 C16 C17 -60.9(3) . . . . ?
C6 C5 C16 C18 62.6(3) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C7 C8 C9 C4 -0.1(3) . . . . ?
C9 C4 C5 C6 -1.0(3) . . . . ?
C9 C4 C5 C16 175.45(18) . . . . ?
C10 C3 C4 C5 178.7(2) . . . . ?
C10 C3 C4 C9 1.3(4) . . . . ?
C10 C11 C12 C13 2.1(3) . . . . ?
C10 C11 O2 C1 0.1(3) . . . . ?
C11 C10 C15 C14 1.7(3) . . . . ?
C11 C12 C13 C14 0.8(3) . . . . ?
C11 C12 C13 C23 -178.9(2) . . . . ?
C12 C11 O2 C1 -179.74(18) . . . . ?
C12 C13 C14 C15 -2.4(3) . . . . ?
C13 C14 C15 C10 1.1(4) . . . . ?
C15 C10 C11 C12 -3.3(3) . . . . ?
C15 C10 C11 O2 176.81(18) . . . . ?
C16 C2 C3 C4 1.1(2) . . . . ?
C16 C2 C3 C10 -177.09(17) . . . . ?
C16 C5 C6 C7 -175.1(2) . . . . ?
C16 C17 O4 C19 -176.72(19) . . . . ?
C16 C18 O6 C21 179.72(17) . . . . ?
C17 C16 C18 O5 -125.4(2) . . . . ?
C17 C16 C18 O6 57.7(2) . . . . ?
C18 C16 C17 O3 8.6(3) . . . . ?
C18 C16 C17 O4 -173.25(16) . . . . ?
C20 C19 O4 C17 173.2(3) . . . . ?
C22 C21 O6 C18 174.9(2) . . . . ?
C23 C13 C14 C15 177.3(2) . . . . ?
O1 C1 C2 C3 172.5(2) . . . . ?
O1 C1 C2 C16 -8.2(3) . . . . ?
O1 C1 O2 C11 -173.81(19) . . . . ?
O2 C1 C2 C3 -7.2(3) . . . . ?
O2 C1 C2 C16 172.10(17) . . . . ?
O2 C11 C12 C13 -178.02(18) . . . . ?
O3 C17 O4 C19 1.4(3) . . . . ?
O5 C18 O6 C21 2.8(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_201711251
_database_code_depnum_ccdc_archive 'CCDC 1858970'
loop_
_audit_author_name
_audit_author_address
'QingRui Li'
;University
China
;
_audit_update_record             
;
2018-07-29 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;
_audit_creation_date             2017-11-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 Br O2'
_chemical_formula_sum            'C16 H11 Br O2'
_chemical_formula_weight         315.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H30N4O4Br1
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.0036(11)
_cell_length_b                   15.5670(13)
_cell_length_c                   8.7599(11)
_cell_angle_alpha                90
_cell_angle_beta                 100.953(11)
_cell_angle_gamma                90
_cell_volume                     1339.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    983
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7580
_cell_measurement_theta_min      4.4950
_shelx_estimated_absorpt_T_max   0.615
_shelx_estimated_absorpt_T_min   0.540
_exptl_absorpt_coefficient_mu    4.138
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.563
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5202
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.089
_diffrn_reflns_theta_max         67.088
_diffrn_reflns_theta_min         4.502
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -107.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  120.0000 71

#__ type_ start__ end____ width___ exp.time_
  2 omega  -63.00  -37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   15.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000   90.0000 46

#__ type_ start__ end____ width___ exp.time_
  4 omega -107.00  -75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  120.0000 32

#__ type_ start__ end____ width___ exp.time_
  5 omega  -33.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000  150.0000 90

#__ type_ start__ end____ width___ exp.time_
  6 omega   72.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
  7 omega   44.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega   27.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
  9 omega   43.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   40.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 40

#__ type_ start__ end____ width___ exp.time_
 11 omega   69.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 35

#__ type_ start__ end____ width___ exp.time_
 12 omega   47.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
 13 omega   41.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 14 omega   42.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 57

#__ type_ start__ end____ width___ exp.time_
 15 omega   89.00  171.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 82

#__ type_ start__ end____ width___ exp.time_
 16 omega   38.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 52

#__ type_ start__ end____ width___ exp.time_
 17 omega   47.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
 18 omega   39.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 47

#__ type_ start__ end____ width___ exp.time_
 19 omega  101.00  165.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 64

#__ type_ start__ end____ width___ exp.time_
 20 omega -100.00  -49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  -30.0000 51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0856806000
_diffrn_orient_matrix_UB_12      -0.0770384000
_diffrn_orient_matrix_UB_13      -0.0356958000
_diffrn_orient_matrix_UB_21      -0.1252178000
_diffrn_orient_matrix_UB_22      -0.0588704000
_diffrn_orient_matrix_UB_23      -0.0119213000
_diffrn_orient_matrix_UB_31      -0.0395749000
_diffrn_orient_matrix_UB_32      0.0197272000
_diffrn_orient_matrix_UB_33      -0.1752339000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1610
_reflns_number_total             2381
_reflns_odcompleteness_completeness 99.44
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0484P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1132
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.90818(5) 0.25445(2) 0.07703(5) 0.06628(19) Uani 1 1 d . . . . .
C1 C 0.6866(4) 0.1803(2) 0.1823(4) 0.0536(10) Uani 1 1 d . . . . .
C2 C 0.7481(4) 0.2630(2) 0.1573(4) 0.0475(8) Uani 1 1 d . . . . .
C3 C 0.6962(4) 0.3389(2) 0.1940(4) 0.0465(9) Uani 1 1 d . . . . .
C4 C 0.5756(4) 0.3385(2) 0.2602(4) 0.0488(9) Uani 1 1 d . . . . .
C5 C 0.5172(4) 0.2603(2) 0.2873(5) 0.0513(9) Uani 1 1 d . . . . .
C6 C 0.4044(4) 0.2542(2) 0.3542(5) 0.0624(11) Uani 1 1 d . . . . .
H6 H 0.3691 0.2006 0.3714 0.075 Uiso 1 1 calc R . . . .
C7 C 0.3427(4) 0.3282(3) 0.3963(5) 0.0641(11) Uani 1 1 d . . . . .
C8 C 0.3986(4) 0.4074(3) 0.3697(5) 0.0663(11) Uani 1 1 d . . . . .
H8 H 0.3584 0.4575 0.3972 0.080 Uiso 1 1 calc R . . . .
C9 C 0.5116(4) 0.4129(2) 0.3037(4) 0.0602(10) Uani 1 1 d . . . . .
H9 H 0.5469 0.4666 0.2871 0.072 Uiso 1 1 calc R . . . .
C10 C 0.2171(5) 0.3221(3) 0.4669(6) 0.0962(16) Uani 1 1 d . . . . .
H10A H 0.2131 0.3707 0.5334 0.144 Uiso 1 1 calc GR . . . .
H10B H 0.2203 0.2702 0.5267 0.144 Uiso 1 1 calc GR . . . .
H10C H 0.1377 0.3215 0.3857 0.144 Uiso 1 1 calc GR . . . .
C11 C 0.7666(4) 0.4220(2) 0.1734(4) 0.0490(9) Uani 1 1 d . . . . .
C12 C 0.7324(5) 0.4698(2) 0.0400(5) 0.0722(13) Uani 1 1 d . . . . .
H12 H 0.6611 0.4524 -0.0380 0.087 Uiso 1 1 calc R . . . .
C13 C 0.8041(5) 0.5442(3) 0.0214(5) 0.0863(16) Uani 1 1 d . . . . .
H13 H 0.7807 0.5766 -0.0690 0.104 Uiso 1 1 calc R . . . .
C14 C 0.9092(5) 0.5698(3) 0.1359(5) 0.0747(13) Uani 1 1 d . . . . .
H14 H 0.9576 0.6195 0.1232 0.090 Uiso 1 1 calc R . . . .
C15 C 0.9425(5) 0.5233(3) 0.2669(5) 0.0783(13) Uani 1 1 d . . . . .
H15 H 1.0143 0.5409 0.3442 0.094 Uiso 1 1 calc R . . . .
C16 C 0.8714(4) 0.4495(2) 0.2876(5) 0.0695(12) Uani 1 1 d . . . . .
H16 H 0.8946 0.4183 0.3794 0.083 Uiso 1 1 calc R . . . .
O1 O 0.7265(3) 0.11095(15) 0.1519(3) 0.0726(8) Uani 1 1 d . . . . .
O2 O 0.5739(3) 0.18364(14) 0.2493(3) 0.0589(7) 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
Br1 C2 1.872(4) . ?
C1 C2 1.460(5) . ?
C1 O1 1.199(4) . ?
C1 O2 1.368(5) . ?
C2 C3 1.355(4) . ?
C3 C4 1.434(5) . ?
C3 C11 1.500(4) . ?
C4 C5 1.390(5) . ?
C4 C9 1.409(5) . ?
C5 C6 1.370(6) . ?
C5 O2 1.389(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.389(5) . ?
C7 C8 1.392(5) . ?
C7 C10 1.506(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.367(5) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.373(5) . ?
C11 C16 1.373(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.367(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.345(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(5) . ?
C16 H16 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
O1 C1 C2 126.3(4) . . ?
O1 C1 O2 117.8(3) . . ?
O2 C1 C2 115.9(3) . . ?
C1 C2 Br1 114.1(3) . . ?
C3 C2 Br1 123.0(3) . . ?
C3 C2 C1 122.8(3) . . ?
C2 C3 C4 118.8(3) . . ?
C2 C3 C11 120.9(3) . . ?
C4 C3 C11 120.2(3) . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 C9 116.5(4) . . ?
C9 C4 C3 124.5(3) . . ?
C6 C5 C4 122.7(4) . . ?
C6 C5 O2 116.7(3) . . ?
O2 C5 C4 120.6(4) . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0(4) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C8 118.5(4) . . ?
C6 C7 C10 120.3(4) . . ?
C8 C7 C10 121.2(4) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.1(4) . . ?
C9 C8 H8 119.4 . . ?
C4 C9 H9 119.4 . . ?
C8 C9 C4 121.2(4) . . ?
C8 C9 H9 119.4 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C3 121.5(3) . . ?
C16 C11 C3 119.5(3) . . ?
C16 C11 C12 118.9(3) . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.1(4) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.0(4) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0(4) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.7(4) . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 120.3(4) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C1 O2 C5 122.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C2 C3 C4 -177.8(3) . . . . ?
Br1 C2 C3 C11 -0.7(5) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C1 C2 C3 C11 177.0(3) . . . . ?
C2 C1 O2 C5 2.1(5) . . . . ?
C2 C3 C4 C5 1.2(5) . . . . ?
C2 C3 C4 C9 179.9(3) . . . . ?
C2 C3 C11 C12 93.7(5) . . . . ?
C2 C3 C11 C16 -83.7(5) . . . . ?
C3 C4 C5 C6 178.1(4) . . . . ?
C3 C4 C5 O2 -0.7(5) . . . . ?
C3 C4 C9 C8 -178.4(4) . . . . ?
C3 C11 C12 C13 -176.8(4) . . . . ?
C3 C11 C16 C15 176.3(4) . . . . ?
C4 C3 C11 C12 -89.3(5) . . . . ?
C4 C3 C11 C16 93.3(4) . . . . ?
C4 C5 C6 C7 0.7(6) . . . . ?
C4 C5 O2 C1 -1.0(5) . . . . ?
C5 C4 C9 C8 0.3(6) . . . . ?
C5 C6 C7 C8 -0.3(6) . . . . ?
C5 C6 C7 C10 178.8(4) . . . . ?
C6 C5 O2 C1 -179.9(3) . . . . ?
C6 C7 C8 C9 0.0(6) . . . . ?
C7 C8 C9 C4 0.0(6) . . . . ?
C9 C4 C5 C6 -0.7(6) . . . . ?
C9 C4 C5 O2 -179.5(3) . . . . ?
C10 C7 C8 C9 -179.1(4) . . . . ?
C11 C3 C4 C5 -175.9(3) . . . . ?
C11 C3 C4 C9 2.8(5) . . . . ?
C11 C12 C13 C14 0.1(8) . . . . ?
C12 C11 C16 C15 -1.2(7) . . . . ?
C12 C13 C14 C15 -0.3(8) . . . . ?
C13 C14 C15 C16 -0.2(8) . . . . ?
C14 C15 C16 C11 1.0(8) . . . . ?
C16 C11 C12 C13 0.7(7) . . . . ?
O1 C1 C2 Br1 -2.5(5) . . . . ?
O1 C1 C2 C3 179.6(4) . . . . ?
O1 C1 O2 C5 -178.9(3) . . . . ?
O2 C1 C2 Br1 176.3(3) . . . . ?
O2 C1 C2 C3 -1.6(5) . . . . ?
O2 C5 C6 C7 179.6(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_201803171
_database_code_depnum_ccdc_archive 'CCDC 1858972'
loop_
_audit_author_name
_audit_author_address
'QingRui Li'
;University
China
;
_audit_update_record             
;
2018-07-29 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;
_audit_creation_date             2018-03-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 O2'
_chemical_formula_sum            'C16 H12 O2'
_chemical_formula_weight         236.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H20N2O8
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.676(2)
_cell_length_b                   4.1792(4)
_cell_length_c                   24.335(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.380(14)
_cell_angle_gamma                90
_cell_volume                     2414.6(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    797
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.6270
_cell_measurement_theta_min      4.4590
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            5181
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.366
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   24.00   0.3500    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.2885  -99.0000 -180.0000 140

#__ type_ start__ end____ width___ exp.time_
  2 omega    7.00   87.85   0.3500    4.5000
omega____ theta____ kappa____ phi______ frames
    -       20.1010   57.0000  120.0000 231

#__ type_ start__ end____ width___ exp.time_
  3 omega  -53.00   63.20   0.3500    4.5000
omega____ theta____ kappa____ phi______ frames
    -       20.1010  -19.0000  120.0000 332
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0224723000
_diffrn_orient_matrix_UB_12      0.0443589000
_diffrn_orient_matrix_UB_13      0.0266370000
_diffrn_orient_matrix_UB_21      -0.0192657000
_diffrn_orient_matrix_UB_22      0.0184801000
_diffrn_orient_matrix_UB_23      0.0143213000
_diffrn_orient_matrix_UB_31      0.0039445000
_diffrn_orient_matrix_UB_32      -0.1627856000
_diffrn_orient_matrix_UB_33      0.0088959000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1394
_reflns_number_total             2469
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2469
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0687
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0866P)²+0.0879P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1635
_refine_ls_wR_factor_ref         0.2052
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
C1 C 0.51174(12) 0.4955(7) 0.35469(14) 0.0678(8) Uani 1 1 d . . . . .
C2 C 0.55469(12) 0.5975(6) 0.33396(12) 0.0601(7) Uani 1 1 d . . . . .
H2 H 0.5503 0.5491 0.2951 0.072 Uiso 1 1 calc R . . . .
C3 C 0.60105(10) 0.7601(6) 0.36843(11) 0.0494(6) Uani 1 1 d . . . . .
C4 C 0.60650(10) 0.8506(5) 0.42776(10) 0.0453(6) Uani 1 1 d . . . . .
C5 C 0.56457(10) 0.7516(6) 0.44762(11) 0.0501(7) Uani 1 1 d . . . . .
C6 C 0.56623(11) 0.8282(6) 0.50372(12) 0.0547(7) Uani 1 1 d . . . . .
H6 H 0.5381 0.7547 0.5158 0.066 Uiso 1 1 calc R . . . .
C7 C 0.60969(12) 1.0140(6) 0.54197(11) 0.0533(7) Uani 1 1 d . . . . .
C8 C 0.65169(12) 1.1169(6) 0.52239(11) 0.0554(7) Uani 1 1 d . . . . .
H8 H 0.6814 1.2400 0.5475 0.067 Uiso 1 1 calc R . . . .
C9 C 0.64994(11) 1.0402(6) 0.46719(11) 0.0519(7) Uani 1 1 d . . . . .
H9 H 0.6782 1.1151 0.4554 0.062 Uiso 1 1 calc R . . . .
C10 C 0.61134(14) 1.1067(8) 0.60261(12) 0.0720(8) Uani 1 1 d . . . . .
H10A H 0.5946 1.3141 0.6005 0.108 Uiso 1 1 calc GR . . . .
H10B H 0.6497 1.1127 0.6304 0.108 Uiso 1 1 calc GR . . . .
H10C H 0.5907 0.9523 0.6155 0.108 Uiso 1 1 calc GR . . . .
C11 C 0.64497(11) 0.8476(6) 0.34461(11) 0.0492(7) Uani 1 1 d . . . . .
C12 C 0.63030(12) 0.9961(6) 0.29021(11) 0.0594(8) Uani 1 1 d . . . . .
H12 H 0.5926 1.0396 0.2678 0.071 Uiso 1 1 calc R . . . .
C13 C 0.67120(15) 1.0819(7) 0.26843(12) 0.0708(9) Uani 1 1 d . . . . .
H13 H 0.6610 1.1879 0.2322 0.085 Uiso 1 1 calc R . . . .
C14 C 0.72707(14) 1.0092(7) 0.30065(13) 0.0660(8) Uani 1 1 d . . . . .
H14 H 0.7546 1.0677 0.2864 0.079 Uiso 1 1 calc R . . . .
C15 C 0.74180(12) 0.8507(6) 0.35361(13) 0.0619(8) Uani 1 1 d . . . . .
H15 H 0.7792 0.7952 0.3746 0.074 Uiso 1 1 calc R . . . .
C16 C 0.70159(11) 0.7723(6) 0.37624(12) 0.0547(7) Uani 1 1 d . . . . .
H16 H 0.7123 0.6689 0.4127 0.066 Uiso 1 1 calc R . . . .
O1 O 0.46971(10) 0.3452(6) 0.32652(10) 0.0998(8) Uani 1 1 d . . . . .
O2 O 0.51943(8) 0.5710(4) 0.41238(8) 0.0636(6) 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 1.441(4) . ?
C1 O1 1.211(3) . ?
C1 O2 1.378(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.350(3) . ?
C3 C4 1.447(3) . ?
C3 C11 1.497(3) . ?
C4 C5 1.400(3) . ?
C4 C9 1.406(3) . ?
C5 C6 1.387(3) . ?
C5 O2 1.375(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.387(4) . ?
C7 C8 1.402(4) . ?
C7 C10 1.511(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.365(3) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.379(3) . ?
C11 C16 1.397(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.391(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.368(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.382(3) . ?
C16 H16 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
O1 C1 C2 126.2(3) . . ?
O1 C1 O2 116.5(3) . . ?
O2 C1 C2 117.2(2) . . ?
C1 C2 H2 118.6 . . ?
C3 C2 C1 122.9(3) . . ?
C3 C2 H2 118.6 . . ?
C2 C3 C4 118.6(2) . . ?
C2 C3 C11 119.9(2) . . ?
C4 C3 C11 121.5(2) . . ?
C5 C4 C3 118.2(2) . . ?
C5 C4 C9 116.5(2) . . ?
C9 C4 C3 125.3(2) . . ?
C6 C5 C4 122.1(2) . . ?
O2 C5 C4 121.6(2) . . ?
O2 C5 C6 116.3(2) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C8 118.0(2) . . ?
C6 C7 C10 121.0(3) . . ?
C8 C7 C10 120.9(3) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.4(3) . . ?
C9 C8 H8 119.3 . . ?
C4 C9 H9 119.2 . . ?
C8 C9 C4 121.6(2) . . ?
C8 C9 H9 119.2 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C3 120.8(2) . . ?
C12 C11 C16 118.5(2) . . ?
C16 C11 C3 120.7(2) . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.8(3) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C11 C16 H16 119.8 . . ?
C15 C16 C11 120.4(3) . . ?
C15 C16 H16 119.8 . . ?
C5 O2 C1 121.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -3.3(4) . . . . ?
C1 C2 C3 C11 177.7(2) . . . . ?
C2 C1 O2 C5 3.6(4) . . . . ?
C2 C3 C4 C5 3.0(3) . . . . ?
C2 C3 C4 C9 -175.0(2) . . . . ?
C2 C3 C11 C12 50.0(3) . . . . ?
C2 C3 C11 C16 -128.2(3) . . . . ?
C3 C4 C5 C6 -179.8(2) . . . . ?
C3 C4 C5 O2 0.5(3) . . . . ?
C3 C4 C9 C8 179.4(2) . . . . ?
C3 C11 C12 C13 179.0(2) . . . . ?
C3 C11 C16 C15 179.3(2) . . . . ?
C4 C3 C11 C12 -129.0(2) . . . . ?
C4 C3 C11 C16 52.9(3) . . . . ?
C4 C5 C6 C7 1.3(4) . . . . ?
C4 C5 O2 C1 -3.9(4) . . . . ?
C5 C4 C9 C8 1.5(3) . . . . ?
C5 C6 C7 C8 -0.7(4) . . . . ?
C5 C6 C7 C10 178.4(2) . . . . ?
C6 C5 O2 C1 176.4(2) . . . . ?
C6 C7 C8 C9 0.6(4) . . . . ?
C7 C8 C9 C4 -1.0(4) . . . . ?
C9 C4 C5 C6 -1.6(4) . . . . ?
C9 C4 C5 O2 178.6(2) . . . . ?
C10 C7 C8 C9 -178.6(2) . . . . ?
C11 C3 C4 C5 -178.0(2) . . . . ?
C11 C3 C4 C9 4.0(4) . . . . ?
C11 C12 C13 C14 2.0(4) . . . . ?
C12 C11 C16 C15 1.1(4) . . . . ?
C12 C13 C14 C15 0.6(4) . . . . ?
C13 C14 C15 C16 -2.3(4) . . . . ?
C14 C15 C16 C11 1.5(4) . . . . ?
C16 C11 C12 C13 -2.8(4) . . . . ?
O1 C1 C2 C3 -178.8(3) . . . . ?
O1 C1 O2 C5 -177.5(2) . . . . ?
O2 C1 C2 C3 0.1(4) . . . . ?
O2 C5 C6 C7 -178.9(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_201803161
_database_code_depnum_ccdc_archive 'CCDC 1858971'
loop_
_audit_author_name
_audit_author_address
'QingRui Li'
;University
China
;
_audit_update_record             
;
2018-07-29 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;
_audit_creation_date             2018-03-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H22 O6'
_chemical_formula_sum            'C23 H22 O6'
_chemical_formula_weight         394.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         C40H30N3O5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.7414(4)
_cell_length_b                   8.7416(3)
_cell_length_c                   16.4090(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.242(3)
_cell_angle_gamma                90
_cell_volume                     2049.53(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2377
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6740
_cell_measurement_theta_min      5.0740
_shelx_estimated_absorpt_T_max   0.894
_shelx_estimated_absorpt_T_min   0.844
_exptl_absorpt_coefficient_mu    0.762
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8150
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.895
_diffrn_reflns_theta_min         5.563
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -40.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega -108.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   30.0000 51

#__ type_ start__ end____ width___ exp.time_
  3 omega   66.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  120.0000 35

#__ type_ start__ end____ width___ exp.time_
  4 omega    8.00   41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000    0.0000 33

#__ type_ start__ end____ width___ exp.time_
  5 omega    9.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -150.0000 91

#__ type_ start__ end____ width___ exp.time_
  6 omega   49.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -90.0000 55

#__ type_ start__ end____ width___ exp.time_
  7 omega   45.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000    0.0000 49

#__ type_ start__ end____ width___ exp.time_
  8 omega  -30.00    8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000    0.0000 38

#__ type_ start__ end____ width___ exp.time_
  9 omega   26.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000    0.0000 33

#__ type_ start__ end____ width___ exp.time_
 10 omega   16.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -90.0000 61

#__ type_ start__ end____ width___ exp.time_
 11 omega   90.00  175.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 85

#__ type_ start__ end____ width___ exp.time_
 12 omega   54.00   93.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 39

#__ type_ start__ end____ width___ exp.time_
 13 omega   38.00  114.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 76

#__ type_ start__ end____ width___ exp.time_
 14 omega   40.00  108.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 68

#__ type_ start__ end____ width___ exp.time_
 15 omega   61.00   87.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega  100.00  175.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 75

#__ type_ start__ end____ width___ exp.time_
 17 omega   70.00   95.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega   60.00   86.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   88.00  169.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0096887000
_diffrn_orient_matrix_UB_12      0.0648257000
_diffrn_orient_matrix_UB_13      0.0889665000
_diffrn_orient_matrix_UB_21      -0.0049004000
_diffrn_orient_matrix_UB_22      0.1638313000
_diffrn_orient_matrix_UB_23      -0.0355036000
_diffrn_orient_matrix_UB_31      -0.1073045000
_diffrn_orient_matrix_UB_32      -0.0016038000
_diffrn_orient_matrix_UB_33      -0.0142665000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2901
_reflns_number_total             3871
_reflns_odcompleteness_completeness 99.90
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3871
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0626
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1037P)²+0.5816P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1809
_refine_ls_wR_factor_ref         0.2038
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C20(H20A,H20B,H20C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.11829(17) 0.4860(3) 0.25885(16) 0.0596(6) Uani 1 1 d . . . . .
C2 C 0.21371(15) 0.4779(3) 0.24811(13) 0.0481(5) Uani 1 1 d . . . . .
C3 C 0.23435(15) 0.5264(2) 0.17623(13) 0.0449(5) Uani 1 1 d . . . . .
C4 C 0.16010(15) 0.5920(3) 0.10962(13) 0.0464(5) Uani 1 1 d . . . . .
C5 C 0.07099(16) 0.6061(3) 0.12360(15) 0.0525(5) Uani 1 1 d . . . . .
C6 C -0.00192(17) 0.6775(3) 0.06740(17) 0.0602(6) Uani 1 1 d . . . . .
H6 H -0.0605 0.6847 0.0789 0.072 Uiso 1 1 calc R . . . .
C7 C 0.01272(18) 0.7383(3) -0.00624(17) 0.0620(6) Uani 1 1 d . . . . .
C8 C 0.10012(19) 0.7236(3) -0.02199(16) 0.0642(7) Uani 1 1 d . . . . .
H8 H 0.1100 0.7623 -0.0719 0.077 Uiso 1 1 calc R . . . .
C9 C 0.17314(17) 0.6529(3) 0.03431(15) 0.0569(6) Uani 1 1 d . . . . .
H9 H 0.2314 0.6457 0.0222 0.068 Uiso 1 1 calc R . . . .
C10 C -0.0658(2) 0.8209(4) -0.0671(2) 0.0859(9) Uani 1 1 d . . . . .
H10A H -0.0892 0.7578 -0.1156 0.129 Uiso 1 1 calc GR . . . .
H10B H -0.0426 0.9152 -0.0841 0.129 Uiso 1 1 calc GR . . . .
H10C H -0.1153 0.8421 -0.0402 0.129 Uiso 1 1 calc GR . . . .
C11 C 0.33151(15) 0.5206(3) 0.16432(13) 0.0507(5) Uani 1 1 d . . . . .
C12 C 0.3518(2) 0.4274(4) 0.10263(18) 0.0701(7) Uani 1 1 d . . . . .
H12 H 0.3052 0.3674 0.0689 0.084 Uiso 1 1 calc R . . . .
C13 C 0.4422(3) 0.4245(5) 0.0917(2) 0.0990(13) Uani 1 1 d . . . . .
H13 H 0.4561 0.3617 0.0506 0.119 Uiso 1 1 calc R . . . .
C14 C 0.5109(2) 0.5127(6) 0.1405(3) 0.1098(15) Uani 1 1 d . . . . .
H14 H 0.5711 0.5100 0.1324 0.132 Uiso 1 1 calc R . . . .
C15 C 0.4915(2) 0.6039(5) 0.2006(2) 0.0955(12) Uani 1 1 d . . . . .
H15 H 0.5388 0.6633 0.2338 0.115 Uiso 1 1 calc R . . . .
C16 C 0.40172(18) 0.6099(4) 0.21347(17) 0.0666(7) Uani 1 1 d . . . . .
H16 H 0.3889 0.6734 0.2547 0.080 Uiso 1 1 calc R . . . .
C17 C 0.28471(16) 0.4163(3) 0.32324(14) 0.0515(5) Uani 1 1 d . . . . .
H17 H 0.3424 0.3968 0.3054 0.062 Uiso 1 1 calc R . . . .
C18 C 0.30745(18) 0.5368(3) 0.39304(16) 0.0613(6) Uani 1 1 d . . . . .
C19 C 0.3985(3) 0.5898(6) 0.5300(3) 0.1202(17) Uani 1 1 d . . . . .
H19A H 0.4655 0.5921 0.5545 0.144 Uiso 1 1 calc R . . . .
H19B H 0.3773 0.6937 0.5159 0.144 Uiso 1 1 calc R . . . .
C20 C 0.3507(6) 0.5256(6) 0.5900(3) 0.171(3) Uani 1 1 d . . . . .
H20A H 0.2869 0.5033 0.5619 0.256 Uiso 1 1 calc GR . . . .
H20B H 0.3521 0.5981 0.6343 0.256 Uiso 1 1 calc GR . . . .
H20C H 0.3815 0.4332 0.6134 0.256 Uiso 1 1 calc GR . . . .
C21 C 0.25505(19) 0.2655(3) 0.35541(15) 0.0614(6) Uani 1 1 d . . . . .
C22 C 0.1986(3) 0.0176(4) 0.3158(2) 0.0876(10) Uani 1 1 d . . . . .
H22A H 0.2469 -0.0282 0.3601 0.105 Uiso 1 1 calc R . . . .
H22B H 0.1429 0.0299 0.3367 0.105 Uiso 1 1 calc R . . . .
C23 C 0.1789(5) -0.0777(4) 0.2455(3) 0.137(2) Uani 1 1 d . . . . .
H23A H 0.1272 -0.0367 0.2038 0.206 Uiso 1 1 calc GR . . . .
H23B H 0.1632 -0.1780 0.2616 0.206 Uiso 1 1 calc GR . . . .
H23C H 0.2329 -0.0841 0.2228 0.206 Uiso 1 1 calc GR . . . .
O1 O 0.09519(14) 0.4394(3) 0.31955(13) 0.0897(8) Uani 1 1 d . . . . .
O2 O 0.05123(11) 0.5497(2) 0.19569(11) 0.0653(5) Uani 1 1 d . . . . .
O3 O 0.26907(18) 0.6556(3) 0.39155(13) 0.0890(7) Uani 1 1 d . . . . .
O4 O 0.37766(17) 0.4938(3) 0.45360(15) 0.1067(10) Uani 1 1 d . . . . .
O5 O 0.25462(19) 0.2404(3) 0.42732(13) 0.0978(8) Uani 1 1 d . . . . .
O6 O 0.23013(15) 0.1677(2) 0.29352(12) 0.0703(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 1.462(3) . ?
C1 O1 1.200(3) . ?
C1 O2 1.363(3) . ?
C2 C3 1.357(3) . ?
C2 C17 1.507(3) . ?
C3 C4 1.460(3) . ?
C3 C11 1.493(3) . ?
C4 C5 1.393(3) . ?
C4 C9 1.402(3) . ?
C5 C6 1.381(3) . ?
C5 O2 1.377(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.385(4) . ?
C7 C8 1.381(4) . ?
C7 C10 1.513(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.380(4) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.388(4) . ?
C11 C16 1.386(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.365(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.352(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.391(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9800 . ?
C17 C18 1.532(3) . ?
C17 C21 1.524(4) . ?
C18 O3 1.180(3) . ?
C18 O4 1.301(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.457(7) . ?
C19 O4 1.477(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O5 1.202(3) . ?
C21 O6 1.309(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.394(5) . ?
C22 O6 1.468(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 124.2(2) . . ?
O1 C1 O2 118.0(2) . . ?
O2 C1 C2 117.9(2) . . ?
C1 C2 C17 114.45(19) . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 C17 124.3(2) . . ?
C2 C3 C4 119.09(19) . . ?
C2 C3 C11 122.0(2) . . ?
C4 C3 C11 118.82(18) . . ?
C5 C4 C3 118.35(19) . . ?
C5 C4 C9 116.8(2) . . ?
C9 C4 C3 124.7(2) . . ?
C6 C5 C4 122.7(2) . . ?
O2 C5 C4 121.1(2) . . ?
O2 C5 C6 116.2(2) . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.6(2) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C10 120.1(3) . . ?
C8 C7 C6 118.7(2) . . ?
C8 C7 C10 121.2(3) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 C7 121.8(2) . . ?
C9 C8 H8 119.1 . . ?
C4 C9 H9 119.8 . . ?
C8 C9 C4 120.4(2) . . ?
C8 C9 H9 119.8 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C3 120.1(2) . . ?
C16 C11 C3 120.5(2) . . ?
C16 C11 C12 119.4(2) . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.4(3) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.7(4) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.8(3) . . ?
C16 C15 H15 119.6 . . ?
C11 C16 C15 119.5(3) . . ?
C11 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C2 C17 H17 107.3 . . ?
C2 C17 C18 110.2(2) . . ?
C2 C17 C21 113.1(2) . . ?
C18 C17 H17 107.3 . . ?
C21 C17 H17 107.3 . . ?
C21 C17 C18 111.4(2) . . ?
O3 C18 C17 125.0(2) . . ?
O3 C18 O4 123.9(3) . . ?
O4 C18 C17 111.0(2) . . ?
H19A C19 H19B 108.3 . . ?
C20 C19 H19A 109.9 . . ?
C20 C19 H19B 109.9 . . ?
C20 C19 O4 108.7(4) . . ?
O4 C19 H19A 109.9 . . ?
O4 C19 H19B 109.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 C21 C17 124.7(3) . . ?
O5 C21 O6 125.0(3) . . ?
O6 C21 C17 110.2(2) . . ?
H22A C22 H22B 108.2 . . ?
C23 C22 H22A 109.7 . . ?
C23 C22 H22B 109.7 . . ?
C23 C22 O6 110.0(3) . . ?
O6 C22 H22A 109.7 . . ?
O6 C22 H22B 109.7 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 O2 C5 122.17(18) . . ?
C18 O4 C19 116.4(3) . . ?
C21 O6 C22 115.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 1.9(3) . . . . ?
C1 C2 C3 C11 179.4(2) . . . . ?
C1 C2 C17 C18 -74.6(3) . . . . ?
C1 C2 C17 C21 50.8(3) . . . . ?
C2 C1 O2 C5 -0.2(4) . . . . ?
C2 C3 C4 C5 1.8(3) . . . . ?
C2 C3 C4 C9 176.8(2) . . . . ?
C2 C3 C11 C12 115.8(3) . . . . ?
C2 C3 C11 C16 -65.4(3) . . . . ?
C2 C17 C18 O3 6.3(4) . . . . ?
C2 C17 C18 O4 -171.3(2) . . . . ?
C2 C17 C21 O5 -128.9(3) . . . . ?
C2 C17 C21 O6 51.1(3) . . . . ?
C3 C2 C17 C18 103.9(3) . . . . ?
C3 C2 C17 C21 -130.7(2) . . . . ?
C3 C4 C5 C6 174.7(2) . . . . ?
C3 C4 C5 O2 -4.7(3) . . . . ?
C3 C4 C9 C8 -174.8(2) . . . . ?
C3 C11 C12 C13 179.3(3) . . . . ?
C3 C11 C16 C15 -179.3(3) . . . . ?
C4 C3 C11 C12 -66.6(3) . . . . ?
C4 C3 C11 C16 112.1(3) . . . . ?
C4 C5 C6 C7 0.0(4) . . . . ?
C4 C5 O2 C1 4.0(4) . . . . ?
C5 C4 C9 C8 0.3(4) . . . . ?
C5 C6 C7 C8 1.0(4) . . . . ?
C5 C6 C7 C10 -178.2(3) . . . . ?
C6 C5 O2 C1 -175.5(2) . . . . ?
C6 C7 C8 C9 -1.3(4) . . . . ?
C7 C8 C9 C4 0.7(4) . . . . ?
C9 C4 C5 C6 -0.6(4) . . . . ?
C9 C4 C5 O2 179.9(2) . . . . ?
C10 C7 C8 C9 177.8(3) . . . . ?
C11 C3 C4 C5 -175.9(2) . . . . ?
C11 C3 C4 C9 -0.9(3) . . . . ?
C11 C12 C13 C14 -0.4(5) . . . . ?
C12 C11 C16 C15 -0.5(4) . . . . ?
C12 C13 C14 C15 0.2(6) . . . . ?
C13 C14 C15 C16 -0.3(6) . . . . ?
C14 C15 C16 C11 0.4(5) . . . . ?
C16 C11 C12 C13 0.5(4) . . . . ?
C17 C2 C3 C4 -176.5(2) . . . . ?
C17 C2 C3 C11 1.0(3) . . . . ?
C17 C18 O4 C19 -171.9(3) . . . . ?
C17 C21 O6 C22 -179.2(2) . . . . ?
C18 C17 C21 O5 -4.1(4) . . . . ?
C18 C17 C21 O6 175.9(2) . . . . ?
C20 C19 O4 C18 93.9(5) . . . . ?
C21 C17 C18 O3 -120.1(3) . . . . ?
C21 C17 C18 O4 62.4(3) . . . . ?
C23 C22 O6 C21 -176.9(4) . . . . ?
O1 C1 C2 C3 177.0(3) . . . . ?
O1 C1 C2 C17 -4.5(4) . . . . ?
O1 C1 O2 C5 -179.9(3) . . . . ?
O2 C1 C2 C3 -2.7(4) . . . . ?
O2 C1 C2 C17 175.9(2) . . . . ?
O2 C5 C6 C7 179.5(2) . . . . ?
O3 C18 O4 C19 10.5(5) . . . . ?
O5 C21 O6 C22 0.8(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_201806307
_database_code_depnum_ccdc_archive 'CCDC 1858974'
loop_
_audit_author_name
_audit_author_address
'QingRui Li'
;University
China
;
_audit_update_record             
;
2018-07-29 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;
_audit_creation_date             2018-06-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 Cl O6'
_chemical_formula_sum            'C22 H17 Cl O6'
_chemical_formula_weight         412.80
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H15O3N1
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.6483(3)
_cell_length_b                   17.4042(4)
_cell_length_c                   15.2455(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.817(2)
_cell_angle_gamma                90
_cell_volume                     3872.98(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5696
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8740
_cell_measurement_theta_min      3.8980
_shelx_estimated_absorpt_T_max   0.789
_shelx_estimated_absorpt_T_min   0.719
_exptl_absorpt_coefficient_mu    2.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16152
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         3.862
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -104.00  -43.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -37.0000  120.0000 61

#__ type_ start__ end____ width___ exp.time_
  2 omega  -72.00  -46.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   26.00   64.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -120.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega  -23.00    2.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega  -31.00   22.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -120.0000 53

#__ type_ start__ end____ width___ exp.time_
  6 omega  -32.00   33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000    0.0000 65

#__ type_ start__ end____ width___ exp.time_
  7 omega    6.00   52.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -60.0000 46

#__ type_ start__ end____ width___ exp.time_
  8 omega   18.00   44.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   21.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   30.0000 34

#__ type_ start__ end____ width___ exp.time_
 10 omega   -1.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -180.0000 76

#__ type_ start__ end____ width___ exp.time_
 11 omega   79.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   96.00  126.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
 13 omega   69.00  115.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 46

#__ type_ start__ end____ width___ exp.time_
 14 omega   60.00  124.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -120.0000 64

#__ type_ start__ end____ width___ exp.time_
 15 omega   90.00  170.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 80

#__ type_ start__ end____ width___ exp.time_
 16 omega   40.00   65.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 17 omega   54.00   98.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 44

#__ type_ start__ end____ width___ exp.time_
 18 omega   48.00   88.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
 19 omega   38.00   66.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 28

#__ type_ start__ end____ width___ exp.time_
 20 omega   46.00   91.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 45

#__ type_ start__ end____ width___ exp.time_
 21 omega   42.00  106.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 64

#__ type_ start__ end____ width___ exp.time_
 22 omega   37.00   72.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 23 omega   45.00   73.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
 24 omega   97.00  122.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -90.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0237160000
_diffrn_orient_matrix_UB_12      0.0657889000
_diffrn_orient_matrix_UB_13      0.0655185000
_diffrn_orient_matrix_UB_21      -0.0168599000
_diffrn_orient_matrix_UB_22      0.0588827000
_diffrn_orient_matrix_UB_23      -0.0750763000
_diffrn_orient_matrix_UB_31      -0.1014805000
_diffrn_orient_matrix_UB_32      0.0056466000
_diffrn_orient_matrix_UB_33      0.0189693000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5474
_reflns_number_total             6898
_reflns_odcompleteness_completeness 99.61
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     548
_refine_ls_number_reflns         6898
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0613
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1094P)²+1.6638P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.1846
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C21-O6A
 1.43 with sigma of 0.02
 C1A-O6'A
 1.43 with sigma of 0.02
 O6'-C21'
 1.43 with sigma of 0.02
 C1A-C1B
 1.55 with sigma of 0.02
 C18'-O5'A
 1.1 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O5'A) \\sim Ueq, Uanis(O5') \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(O5A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O5') = Uanis(O5'A)
Uanis(O6') = Uanis(O6'A)
Uanis(C21') = Uanis(C1A)
Uanis(C22') = Uanis(C1B)
Uanis(O5) = Uanis(O5A)
Uanis(O6) = Uanis(O6A)
4. Others
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=Sof(O5'A)=
 Sof(O6'A)=1-FVAR(1)
 Sof(C21')=Sof(H21A)=Sof(H21B)=Sof(C22')=Sof(H22A)=Sof(H22B)=Sof(H22C)=
 Sof(O5')=Sof(O6')=FVAR(1)
 Sof(H21E)=Sof(H21F)=Sof(O5A)=Sof(O6A)=1-FVAR(2)
 Sof(H21C)=Sof(H21D)=Sof(O5)=Sof(O6)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C19(H19C,H19D), C21(H21C,H21D), C21(H21E,H21F), C1A(H1AA,H1AB), C19'(H19A,
 H19B), C21'(H21A,H21B)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C6'(H6'),
 C7'(H7'), C8'(H8'), C9'(H9'), C10'(H10'), C12'(H12'), C13'(H13')
5.c Idealised Me refined as rotating group:
 C20(H20D,H20E,H20F), C22(H22D,H22E,H22F), C1B(H1BA,H1BB,H1BC), C20'(H20A,H20B,
 H20C), C22'(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.62103(16) 0.30466(13) 0.17492(16) 0.0376(5) Uani 1 1 d . . . . .
C2 C 0.68993(15) 0.25657(12) 0.22110(14) 0.0315(5) Uani 1 1 d . . . . .
C3 C 0.68695(15) 0.17876(13) 0.21885(14) 0.0320(5) Uani 1 1 d . . . . .
C4 C 0.60827(16) 0.14003(14) 0.17539(15) 0.0372(5) Uani 1 1 d . . . . .
C5 C 0.54127(17) 0.18677(15) 0.13293(16) 0.0407(5) Uani 1 1 d . . . . .
C6 C 0.46376(19) 0.15628(18) 0.08655(19) 0.0528(7) Uani 1 1 d . . . . .
H6 H 0.4199 0.1882 0.0579 0.063 Uiso 1 1 calc R . . . .
C7 C 0.4537(2) 0.0775(2) 0.0842(2) 0.0593(8) Uani 1 1 d . . . . .
H7 H 0.4025 0.0562 0.0531 0.071 Uiso 1 1 calc R . . . .
C8 C 0.5170(2) 0.03037(17) 0.1264(2) 0.0588(8) Uani 1 1 d . . . . .
H8 H 0.5082 -0.0225 0.1245 0.071 Uiso 1 1 calc R . . . .
C9 C 0.5944(2) 0.06049(16) 0.17208(19) 0.0494(6) Uani 1 1 d . . . . .
H9 H 0.6374 0.0278 0.2007 0.059 Uiso 1 1 calc R . . . .
C10 C 0.91623(17) 0.20216(15) 0.32786(17) 0.0421(5) Uani 1 1 d . . . . .
H10 H 0.9530 0.2443 0.3438 0.051 Uiso 1 1 calc R . . . .
C11 C 0.94677(18) 0.12774(16) 0.34389(19) 0.0479(6) Uani 1 1 d . . . . .
C12 C 0.8937(2) 0.06453(16) 0.3204(2) 0.0518(7) Uani 1 1 d . . . . .
H12 H 0.9162 0.0153 0.3322 0.062 Uiso 1 1 calc R . . . .
C13 C 0.80640(19) 0.07438(14) 0.27891(19) 0.0462(6) Uani 1 1 d . . . . .
H13 H 0.7703 0.0320 0.2625 0.055 Uiso 1 1 calc R . . . .
C14 C 0.77359(16) 0.14866(13) 0.26216(15) 0.0343(5) Uani 1 1 d . . . . .
C15 C 0.82925(15) 0.21117(13) 0.28734(15) 0.0340(5) Uani 1 1 d . . . . .
C16 C 0.77819(15) 0.28613(12) 0.26705(14) 0.0325(5) Uani 1 1 d . . . . .
C17 C 0.82934(17) 0.33991(13) 0.20835(17) 0.0400(5) Uani 1 1 d . . . . .
C18 C 0.76709(18) 0.32958(14) 0.35413(16) 0.0421(6) Uani 1 1 d . . . . .
C19 C 0.8665(2) 0.36296(18) 0.0623(2) 0.0550(7) Uani 1 1 d . . . . .
H19C H 0.8856 0.3310 0.0150 0.066 Uiso 1 1 calc R . . . .
H19D H 0.9202 0.3886 0.0899 0.066 Uiso 1 1 calc R . . . .
C20 C 0.7992(3) 0.4210(2) 0.0260(3) 0.0798(11) Uani 1 1 d . . . . .
H20D H 0.8272 0.4531 -0.0153 0.120 Uiso 1 1 calc GR . . . .
H20E H 0.7798 0.4520 0.0731 0.120 Uiso 1 1 calc GR . . . .
H20F H 0.7471 0.3954 -0.0031 0.120 Uiso 1 1 calc GR . . . .
C21 C 0.6784(3) 0.4143(3) 0.4305(3) 0.0880(13) Uani 1 1 d D . . . .
H21C H 0.6772 0.3837 0.4836 0.106 Uiso 0.843(8) 1 calc R . P A 1
H21D H 0.7291 0.4502 0.4385 0.106 Uiso 0.843(8) 1 calc R . P A 1
H21E H 0.6679 0.3682 0.4639 0.106 Uiso 0.157(8) 1 calc R . P A 2
H21F H 0.7218 0.4462 0.4656 0.106 Uiso 0.157(8) 1 calc R . P A 2
C22 C 0.5945(3) 0.4549(2) 0.4139(3) 0.0794(11) Uani 1 1 d . . . . .
H22D H 0.5967 0.4855 0.3617 0.119 Uiso 1 1 calc GR . . . .
H22E H 0.5853 0.4877 0.4630 0.119 Uiso 1 1 calc GR . . . .
H22F H 0.5448 0.4189 0.4059 0.119 Uiso 1 1 calc GR . . . .
Cl1 Cl 1.05498(5) 0.11445(5) 0.39721(7) 0.0770(3) Uani 1 1 d . . . . .
O1 O 0.54770(12) 0.26588(10) 0.13318(12) 0.0458(4) Uani 1 1 d . . . . .
O2 O 0.62229(14) 0.37312(10) 0.16737(14) 0.0540(5) Uani 1 1 d . . . . .
O3 O 0.8669(2) 0.39696(15) 0.23436(18) 0.0895(9) Uani 1 1 d . . . . .
O4 O 0.82509(13) 0.31495(10) 0.12714(11) 0.0440(4) Uani 1 1 d . . . . .
O5 O 0.8268(4) 0.3301(3) 0.4134(2) 0.0971(17) Uani 0.843(8) 1 d . U P A 1
O5A O 0.7743(19) 0.3041(16) 0.4236(14) 0.0971(17) Uani 0.157(8) 1 d . U P A 2
O6 O 0.6895(2) 0.3644(2) 0.35450(19) 0.0577(9) Uani 0.843(8) 1 d . . P A 1
O6A O 0.7194(12) 0.3921(13) 0.3439(10) 0.0577(9) Uani 0.157(8) 1 d D . P A 2
C1' C 0.10766(19) 0.46745(15) 0.17260(19) 0.0465(6) Uani 1 1 d . . . . .
C1A C 0.150(3) 0.347(4) 0.407(3) 0.100(3) Uani 0.237(10) 1 d D . P B 2
H1AA H 0.1057 0.3093 0.3837 0.120 Uiso 0.237(10) 1 calc R . P B 2
H1AB H 0.1193 0.3867 0.4375 0.120 Uiso 0.237(10) 1 calc R . P B 2
C1B C 0.226(4) 0.3084(19) 0.468(3) 0.096(3) Uani 0.237(10) 1 d D . P B 2
H1BA H 0.2683 0.2825 0.4338 0.143 Uiso 0.237(10) 1 calc GR . P B 2
H1BB H 0.1989 0.2719 0.5058 0.143 Uiso 0.237(10) 1 calc GR . P B 2
H1BC H 0.2579 0.3470 0.5041 0.143 Uiso 0.237(10) 1 calc GR . P B 2
C2' C 0.17200(17) 0.51581(13) 0.22380(15) 0.0367(5) Uani 1 1 d . . . . .
C3' C 0.16703(17) 0.59363(13) 0.22367(15) 0.0375(5) Uani 1 1 d . . . . .
C4' C 0.08804(17) 0.63128(14) 0.17885(16) 0.0401(5) Uani 1 1 d . . . . .
C5' C 0.02438(18) 0.58414(15) 0.13267(18) 0.0463(6) Uani 1 1 d . . . . .
C6' C -0.0536(2) 0.61437(19) 0.0859(2) 0.0588(7) Uani 1 1 d . . . . .
H6' H -0.0958 0.5820 0.0555 0.071 Uiso 1 1 calc R . . . .
C7' C -0.0671(2) 0.6918(2) 0.0853(2) 0.0666(9) Uani 1 1 d . . . . .
H7' H -0.1181 0.7124 0.0532 0.080 Uiso 1 1 calc R . . . .
C8' C -0.0058(2) 0.73988(18) 0.1320(2) 0.0594(8) Uani 1 1 d . . . . .
H8' H -0.0164 0.7926 0.1324 0.071 Uiso 1 1 calc R . . . .
C9' C 0.0713(2) 0.70994(15) 0.17829(19) 0.0490(6) Uani 1 1 d . . . . .
H9' H 0.1124 0.7427 0.2094 0.059 Uiso 1 1 calc R . . . .
C10' C 0.39281(19) 0.57388(15) 0.34025(17) 0.0459(6) Uani 1 1 d . . . . .
H10' H 0.4293 0.5323 0.3587 0.055 Uiso 1 1 calc R . . . .
C11' C 0.4228(2) 0.64876(17) 0.35400(19) 0.0508(6) Uani 1 1 d . . . . .
C12' C 0.3693(2) 0.71081(15) 0.3269(2) 0.0524(7) Uani 1 1 d . . . . .
H12' H 0.3911 0.7604 0.3374 0.063 Uiso 1 1 calc R . . . .
C13' C 0.2833(2) 0.69956(14) 0.28424(19) 0.0484(6) Uani 1 1 d . . . . .
H13' H 0.2474 0.7414 0.2655 0.058 Uiso 1 1 calc R . . . .
C14' C 0.25090(18) 0.62492(13) 0.26947(16) 0.0393(5) Uani 1 1 d . . . . .
C15' C 0.30630(17) 0.56346(13) 0.29790(16) 0.0382(5) Uani 1 1 d . . . . .
C16' C 0.25897(18) 0.48756(12) 0.27511(16) 0.0383(5) Uani 1 1 d . . . . .
C17' C 0.31805(18) 0.43494(13) 0.22268(18) 0.0440(6) Uani 1 1 d . . . . .
C18' C 0.2371(2) 0.44488(15) 0.36076(18) 0.0544(7) Uani 1 1 d D . . . .
C19' C 0.3712(2) 0.4131(2) 0.0817(2) 0.0651(8) Uani 1 1 d . . . . .
H19A H 0.4238 0.3907 0.1152 0.078 Uiso 1 1 calc R . . . .
H19B H 0.3934 0.4466 0.0373 0.078 Uiso 1 1 calc R . . . .
C20' C 0.3142(3) 0.3519(3) 0.0390(3) 0.0915(13) Uani 1 1 d . . . . .
H20A H 0.3503 0.3221 0.0018 0.137 Uiso 1 1 calc GR . . . .
H20B H 0.2635 0.3745 0.0041 0.137 Uiso 1 1 calc GR . . . .
H20C H 0.2917 0.3194 0.0831 0.137 Uiso 1 1 calc GR . . . .
C21' C 0.1495(9) 0.3510(12) 0.4297(8) 0.100(3) Uani 0.763(10) 1 d D . P B 1
H21A H 0.1506 0.3851 0.4801 0.120 Uiso 0.763(10) 1 calc R . P B 1
H21B H 0.0879 0.3307 0.4196 0.120 Uiso 0.763(10) 1 calc R . P B 1
C22' C 0.2102(10) 0.2894(4) 0.4504(7) 0.096(3) Uani 0.763(10) 1 d . . P B 1
H22A H 0.2143 0.2579 0.3992 0.143 Uiso 0.763(10) 1 calc GR . P B 1
H22B H 0.1879 0.2592 0.4967 0.143 Uiso 0.763(10) 1 calc GR . P B 1
H22C H 0.2698 0.3093 0.4693 0.143 Uiso 0.763(10) 1 calc GR . P B 1
Cl1' Cl 0.53060(6) 0.66491(5) 0.40645(6) 0.0726(3) Uani 1 1 d . . . . .
O1' O 0.03454(13) 0.50572(11) 0.12904(14) 0.0531(5) Uani 1 1 d . . . . .
O2' O 0.11216(15) 0.39963(11) 0.16089(17) 0.0648(6) Uani 1 1 d . . . . .
O3' O 0.3595(2) 0.38220(15) 0.25472(18) 0.0857(8) Uani 1 1 d . . . . .
O4' O 0.31727(14) 0.45755(11) 0.14017(13) 0.0531(5) Uani 1 1 d . . . . .
O5' O 0.2599(5) 0.4659(3) 0.4321(2) 0.0991(19) Uani 0.763(10) 1 d . U P B 1
O5'A O 0.3068(13) 0.4410(9) 0.4145(9) 0.0991(19) Uani 0.237(10) 1 d D U P B 2
O6' O 0.1706(3) 0.3967(3) 0.3510(4) 0.0790(15) Uani 0.763(10) 1 d D . P B 1
O6'A O 0.2021(11) 0.3786(12) 0.3380(14) 0.0790(15) Uani 0.237(10) 1 d D . P B 2


_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 1.448(3) . ?
C1 O1 1.378(3) . ?
C1 O2 1.197(3) . ?
C2 C3 1.355(3) . ?
C2 C16 1.508(3) . ?
C3 C4 1.447(3) . ?
C3 C14 1.477(3) . ?
C4 C5 1.392(4) . ?
C4 C9 1.399(4) . ?
C5 C6 1.391(4) . ?
C5 O1 1.380(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.380(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.359(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.384(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.385(4) . ?
C10 C15 1.377(3) . ?
C11 C12 1.377(4) . ?
C11 Cl1 1.735(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.395(3) . ?
C14 C15 1.394(3) . ?
C15 C16 1.523(3) . ?
C16 C17 1.533(3) . ?
C16 C18 1.548(3) . ?
C17 O3 1.187(3) . ?
C17 O4 1.309(3) . ?
C18 O5 1.204(4) . ?
C18 O5A 1.15(3) . ?
C18 O6 1.289(4) . ?
C18 O6A 1.296(19) . ?
C19 H19C 0.9700 . ?
C19 H19D 0.9700 . ?
C19 C20 1.485(5) . ?
C19 O4 1.464(3) . ?
C20 H20D 0.9600 . ?
C20 H20E 0.9600 . ?
C20 H20F 0.9600 . ?
C21 H21C 0.9700 . ?
C21 H21D 0.9700 . ?
C21 H21E 0.9700 . ?
C21 H21F 0.9700 . ?
C21 C22 1.422(5) . ?
C21 O6 1.468(4) . ?
C21 O6A 1.545(14) . ?
C22 H22D 0.9600 . ?
C22 H22E 0.9600 . ?
C22 H22F 0.9600 . ?
C1' C2' 1.443(4) . ?
C1' O1' 1.383(3) . ?
C1' O2' 1.196(3) . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C1A C1B 1.54(2) . ?
C1A O6'A 1.459(19) . ?
C1B H1BA 0.9600 . ?
C1B H1BB 0.9600 . ?
C1B H1BC 0.9600 . ?
C2' C3' 1.356(3) . ?
C2' C16' 1.520(3) . ?
C3' C4' 1.450(4) . ?
C3' C14' 1.466(4) . ?
C4' C5' 1.388(4) . ?
C4' C9' 1.391(4) . ?
C5' C6' 1.398(4) . ?
C5' O1' 1.375(3) . ?
C6' H6' 0.9300 . ?
C6' C7' 1.362(5) . ?
C7' H7' 0.9300 . ?
C7' C8' 1.381(5) . ?
C8' H8' 0.9300 . ?
C8' C9' 1.382(4) . ?
C9' H9' 0.9300 . ?
C10' H10' 0.9300 . ?
C10' C11' 1.385(4) . ?
C10' C15' 1.385(4) . ?
C11' C12' 1.377(4) . ?
C11' Cl1' 1.732(3) . ?
C12' H12' 0.9300 . ?
C12' C13' 1.382(4) . ?
C13' H13' 0.9300 . ?
C13' C14' 1.395(3) . ?
C14' C15' 1.390(3) . ?
C15' C16' 1.519(3) . ?
C16' C17' 1.531(3) . ?
C16' C18' 1.559(4) . ?
C17' O3' 1.183(3) . ?
C17' O4' 1.317(3) . ?
C18' O5' 1.169(5) . ?
C18' O5'A 1.257(15) . ?
C18' O6' 1.283(6) . ?
C18' O6'A 1.30(2) . ?
C19' H19A 0.9700 . ?
C19' H19B 0.9700 . ?
C19' C20' 1.471(5) . ?
C19' O4' 1.462(3) . ?
C20' H20A 0.9600 . ?
C20' H20B 0.9600 . ?
C20' H20C 0.9600 . ?
C21' H21A 0.9700 . ?
C21' H21B 0.9700 . ?
C21' C22' 1.411(14) . ?
C21' O6' 1.493(7) . ?
C22' H22A 0.9600 . ?
C22' H22B 0.9600 . ?
C22' H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 115.2(2) . . ?
O2 C1 C2 127.3(2) . . ?
O2 C1 O1 117.4(2) . . ?
C1 C2 C16 124.3(2) . . ?
C3 C2 C1 123.1(2) . . ?
C3 C2 C16 112.2(2) . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 C14 108.6(2) . . ?
C4 C3 C14 131.4(2) . . ?
C5 C4 C3 116.4(2) . . ?
C5 C4 C9 117.8(2) . . ?
C9 C4 C3 125.8(2) . . ?
C6 C5 C4 121.8(3) . . ?
O1 C5 C4 122.4(2) . . ?
O1 C5 C6 115.8(2) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 C5 118.3(3) . . ?
C7 C6 H6 120.9 . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.3(3) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.5(3) . . ?
C9 C8 H8 119.7 . . ?
C4 C9 H9 119.9 . . ?
C8 C9 C4 120.2(3) . . ?
C8 C9 H9 119.9 . . ?
C11 C10 H10 121.4 . . ?
C15 C10 H10 121.4 . . ?
C15 C10 C11 117.3(2) . . ?
C10 C11 Cl1 118.4(2) . . ?
C12 C11 C10 122.3(2) . . ?
C12 C11 Cl1 119.3(2) . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.9(2) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.2(2) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 C3 132.9(2) . . ?
C15 C14 C3 107.88(19) . . ?
C15 C14 C13 119.2(2) . . ?
C10 C15 C14 122.2(2) . . ?
C10 C15 C16 127.5(2) . . ?
C14 C15 C16 110.29(19) . . ?
C2 C16 C15 100.92(17) . . ?
C2 C16 C17 112.27(18) . . ?
C2 C16 C18 114.66(19) . . ?
C15 C16 C17 112.70(19) . . ?
C15 C16 C18 109.23(18) . . ?
C17 C16 C18 107.09(19) . . ?
O3 C17 C16 123.5(2) . . ?
O3 C17 O4 125.3(3) . . ?
O4 C17 C16 111.27(19) . . ?
O5 C18 C16 121.7(3) . . ?
O5 C18 O6 125.4(3) . . ?
O5A C18 C16 126.6(11) . . ?
O5A C18 O6A 116.3(12) . . ?
O6 C18 C16 112.9(2) . . ?
O6A C18 C16 113.7(7) . . ?
H19C C19 H19D 108.2 . . ?
C20 C19 H19C 109.7 . . ?
C20 C19 H19D 109.7 . . ?
O4 C19 H19C 109.7 . . ?
O4 C19 H19D 109.7 . . ?
O4 C19 C20 109.9(3) . . ?
C19 C20 H20D 109.5 . . ?
C19 C20 H20E 109.5 . . ?
C19 C20 H20F 109.5 . . ?
H20D C20 H20E 109.5 . . ?
H20D C20 H20F 109.5 . . ?
H20E C20 H20F 109.5 . . ?
H21C C21 H21D 108.5 . . ?
H21E C21 H21F 108.0 . . ?
C22 C21 H21C 110.2 . . ?
C22 C21 H21D 110.2 . . ?
C22 C21 H21E 109.4 . . ?
C22 C21 H21F 109.4 . . ?
C22 C21 O6 107.8(3) . . ?
C22 C21 O6A 111.4(7) . . ?
O6 C21 H21C 110.2 . . ?
O6 C21 H21D 110.2 . . ?
O6A C21 H21E 109.4 . . ?
O6A C21 H21F 109.4 . . ?
C21 C22 H22D 109.5 . . ?
C21 C22 H22E 109.5 . . ?
C21 C22 H22F 109.5 . . ?
H22D C22 H22E 109.5 . . ?
H22D C22 H22F 109.5 . . ?
H22E C22 H22F 109.5 . . ?
C1 O1 C5 122.70(19) . . ?
C17 O4 C19 117.4(2) . . ?
C18 O6 C21 116.0(3) . . ?
C18 O6A C21 110.6(13) . . ?
O1' C1' C2' 115.0(2) . . ?
O2' C1' C2' 127.9(3) . . ?
O2' C1' O1' 117.0(3) . . ?
H1AA C1A H1AB 109.2 . . ?
C1B C1A H1AA 111.3 . . ?
C1B C1A H1AB 111.3 . . ?
O6'A C1A H1AA 111.3 . . ?
O6'A C1A H1AB 111.3 . . ?
O6'A C1A C1B 102(3) . . ?
C1A C1B H1BA 109.5 . . ?
C1A C1B H1BB 109.5 . . ?
C1A C1B H1BC 109.5 . . ?
H1BA C1B H1BB 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?
C1' C2' C16' 124.8(2) . . ?
C3' C2' C1' 123.3(2) . . ?
C3' C2' C16' 111.5(2) . . ?
C2' C3' C4' 119.5(2) . . ?
C2' C3' C14' 109.1(2) . . ?
C4' C3' C14' 131.3(2) . . ?
C5' C4' C3' 116.6(2) . . ?
C5' C4' C9' 117.9(3) . . ?
C9' C4' C3' 125.5(2) . . ?
C4' C5' C6' 121.4(3) . . ?
O1' C5' C4' 122.5(2) . . ?
O1' C5' C6' 116.1(3) . . ?
C5' C6' H6' 120.4 . . ?
C7' C6' C5' 119.2(3) . . ?
C7' C6' H6' 120.4 . . ?
C6' C7' H7' 119.7 . . ?
C6' C7' C8' 120.6(3) . . ?
C8' C7' H7' 119.7 . . ?
C7' C8' H8' 119.9 . . ?
C7' C8' C9' 120.2(3) . . ?
C9' C8' H8' 119.9 . . ?
C4' C9' H9' 119.6 . . ?
C8' C9' C4' 120.7(3) . . ?
C8' C9' H9' 119.6 . . ?
C11' C10' H10' 121.3 . . ?
C15' C10' H10' 121.3 . . ?
C15' C10' C11' 117.4(3) . . ?
C10' C11' Cl1' 119.2(2) . . ?
C12' C11' C10' 121.8(3) . . ?
C12' C11' Cl1' 119.0(2) . . ?
C11' C12' H12' 119.9 . . ?
C11' C12' C13' 120.2(2) . . ?
C13' C12' H12' 119.9 . . ?
C12' C13' H13' 120.2 . . ?
C12' C13' C14' 119.5(3) . . ?
C14' C13' H13' 120.2 . . ?
C13' C14' C3' 133.1(2) . . ?
C15' C14' C3' 107.9(2) . . ?
C15' C14' C13' 119.0(2) . . ?
C10' C15' C14' 122.1(2) . . ?
C10' C15' C16' 127.1(2) . . ?
C14' C15' C16' 110.8(2) . . ?
C2' C16' C17' 114.3(2) . . ?
C2' C16' C18' 111.3(2) . . ?
C15' C16' C2' 100.56(18) . . ?
C15' C16' C17' 111.9(2) . . ?
C15' C16' C18' 110.2(2) . . ?
C17' C16' C18' 108.5(2) . . ?
O3' C17' C16' 122.8(3) . . ?
O3' C17' O4' 126.1(3) . . ?
O4' C17' C16' 111.1(2) . . ?
O5' C18' C16' 124.5(3) . . ?
O5' C18' O6' 117.8(5) . . ?
O5'A C18' C16' 111.0(7) . . ?
O5'A C18' O6'A 114.1(11) . . ?
O6' C18' C16' 114.9(3) . . ?
O6'A C18' C16' 107.7(9) . . ?
H19A C19' H19B 108.2 . . ?
C20' C19' H19A 109.7 . . ?
C20' C19' H19B 109.7 . . ?
O4' C19' H19A 109.7 . . ?
O4' C19' H19B 109.7 . . ?
O4' C19' C20' 109.7(3) . . ?
C19' C20' H20A 109.5 . . ?
C19' C20' H20B 109.5 . . ?
C19' C20' H20C 109.5 . . ?
H20A C20' H20B 109.5 . . ?
H20A C20' H20C 109.5 . . ?
H20B C20' H20C 109.5 . . ?
H21A C21' H21B 107.6 . . ?
C22' C21' H21A 108.6 . . ?
C22' C21' H21B 108.6 . . ?
C22' C21' O6' 114.5(10) . . ?
O6' C21' H21A 108.6 . . ?
O6' C21' H21B 108.6 . . ?
C21' C22' H22A 109.5 . . ?
C21' C22' H22B 109.5 . . ?
C21' C22' H22C 109.5 . . ?
H22A C22' H22B 109.5 . . ?
H22A C22' H22C 109.5 . . ?
H22B C22' H22C 109.5 . . ?
C5' O1' C1' 122.8(2) . . ?
C17' O4' C19' 117.6(2) . . ?
C18' O6' C21' 117.5(8) . . ?
C18' O6'A C1A 111(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
C1 C2 C3 C4 -5.7(3) . . . . ?
C1 C2 C3 C14 172.1(2) . . . . ?
C1 C2 C16 C15 -169.8(2) . . . . ?
C1 C2 C16 C17 -49.5(3) . . . . ?
C1 C2 C16 C18 73.0(3) . . . . ?
C2 C1 O1 C5 -1.9(3) . . . . ?
C2 C3 C4 C5 3.8(3) . . . . ?
C2 C3 C4 C9 -176.6(2) . . . . ?
C2 C3 C14 C13 179.3(3) . . . . ?
C2 C3 C14 C15 -2.1(3) . . . . ?
C2 C16 C17 O3 139.5(3) . . . . ?
C2 C16 C17 O4 -40.0(3) . . . . ?
C2 C16 C18 O5 150.4(4) . . . . ?
C2 C16 C18 O5A 95(2) . . . . ?
C2 C16 C18 O6 -30.4(4) . . . . ?
C2 C16 C18 O6A -63.6(11) . . . . ?
C3 C2 C16 C15 2.9(2) . . . . ?
C3 C2 C16 C17 123.1(2) . . . . ?
C3 C2 C16 C18 -114.3(2) . . . . ?
C3 C4 C5 C6 178.0(2) . . . . ?
C3 C4 C5 O1 -1.3(3) . . . . ?
C3 C4 C9 C8 -178.4(3) . . . . ?
C3 C14 C15 C10 -178.4(2) . . . . ?
C3 C14 C15 C16 4.0(3) . . . . ?
C4 C3 C14 C13 -3.3(4) . . . . ?
C4 C3 C14 C15 175.4(2) . . . . ?
C4 C5 C6 C7 0.8(4) . . . . ?
C4 C5 O1 C1 0.4(4) . . . . ?
C5 C4 C9 C8 1.2(4) . . . . ?
C5 C6 C7 C8 0.5(5) . . . . ?
C6 C5 O1 C1 -178.9(2) . . . . ?
C6 C7 C8 C9 -0.9(5) . . . . ?
C7 C8 C9 C4 0.1(5) . . . . ?
C9 C4 C5 C6 -1.6(4) . . . . ?
C9 C4 C5 O1 179.1(2) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
C10 C15 C16 C2 178.4(2) . . . . ?
C10 C15 C16 C17 58.5(3) . . . . ?
C10 C15 C16 C18 -60.4(3) . . . . ?
C11 C10 C15 C14 -0.7(4) . . . . ?
C11 C10 C15 C16 176.5(2) . . . . ?
C11 C12 C13 C14 -0.4(4) . . . . ?
C12 C13 C14 C3 178.6(3) . . . . ?
C12 C13 C14 C15 0.1(4) . . . . ?
C13 C14 C15 C10 0.5(4) . . . . ?
C13 C14 C15 C16 -177.1(2) . . . . ?
C14 C3 C4 C5 -173.4(2) . . . . ?
C14 C3 C4 C9 6.2(4) . . . . ?
C14 C15 C16 C2 -4.2(2) . . . . ?
C14 C15 C16 C17 -124.1(2) . . . . ?
C14 C15 C16 C18 117.0(2) . . . . ?
C15 C10 C11 C12 0.4(4) . . . . ?
C15 C10 C11 Cl1 -178.5(2) . . . . ?
C15 C16 C17 O3 -107.4(3) . . . . ?
C15 C16 C17 O4 73.2(3) . . . . ?
C15 C16 C18 O5 38.0(5) . . . . ?
C15 C16 C18 O5A -18(2) . . . . ?
C15 C16 C18 O6 -142.8(3) . . . . ?
C15 C16 C18 O6A -176.0(11) . . . . ?
C16 C2 C3 C4 -178.49(19) . . . . ?
C16 C2 C3 C14 -0.7(3) . . . . ?
C16 C17 O4 C19 176.5(2) . . . . ?
C16 C18 O6 C21 -173.0(4) . . . . ?
C16 C18 O6A C21 157.2(8) . . . . ?
C17 C16 C18 O5 -84.3(5) . . . . ?
C17 C16 C18 O5A -140(2) . . . . ?
C17 C16 C18 O6 94.9(3) . . . . ?
C17 C16 C18 O6A 61.7(11) . . . . ?
C18 C16 C17 O3 12.7(4) . . . . ?
C18 C16 C17 O4 -166.7(2) . . . . ?
C20 C19 O4 C17 -86.4(3) . . . . ?
C22 C21 O6 C18 172.6(4) . . . . ?
C22 C21 O6A C18 -150.7(10) . . . . ?
Cl1 C11 C12 C13 179.0(2) . . . . ?
O1 C1 C2 C3 4.6(3) . . . . ?
O1 C1 C2 C16 176.5(2) . . . . ?
O1 C5 C6 C7 -179.9(3) . . . . ?
O2 C1 C2 C3 -173.3(3) . . . . ?
O2 C1 C2 C16 -1.3(4) . . . . ?
O2 C1 O1 C5 176.2(2) . . . . ?
O3 C17 O4 C19 -2.9(4) . . . . ?
O5 C18 O6 C21 6.2(6) . . . . ?
O5A C18 O6A C21 -3.3(19) . . . . ?
C1' C2' C3' C4' 7.6(4) . . . . ?
C1' C2' C3' C14' -170.0(2) . . . . ?
C1' C2' C16' C15' 168.7(2) . . . . ?
C1' C2' C16' C17' 48.7(3) . . . . ?
C1' C2' C16' C18' -74.6(3) . . . . ?
C1B C1A O6'A C18' -83(4) . . . . ?
C2' C1' O1' C5' 1.1(4) . . . . ?
C2' C3' C4' C5' -4.5(3) . . . . ?
C2' C3' C4' C9' 175.6(2) . . . . ?
C2' C3' C14' C13' 176.1(3) . . . . ?
C2' C3' C14' C15' -0.5(3) . . . . ?
C2' C16' C17' O3' -144.0(3) . . . . ?
C2' C16' C17' O4' 37.4(3) . . . . ?
C2' C16' C18' O5' -115.8(6) . . . . ?
C2' C16' C18' O5'A -161.2(9) . . . . ?
C2' C16' C18' O6' 45.2(4) . . . . ?
C2' C16' C18' O6'A 73.3(8) . . . . ?
C3' C2' C16' C15' -4.4(3) . . . . ?
C3' C2' C16' C17' -124.4(2) . . . . ?
C3' C2' C16' C18' 112.3(2) . . . . ?
C3' C4' C5' C6' -179.0(3) . . . . ?
C3' C4' C5' O1' 0.1(4) . . . . ?
C3' C4' C9' C8' 178.9(3) . . . . ?
C3' C14' C15' C10' 177.0(2) . . . . ?
C3' C14' C15' C16' -2.4(3) . . . . ?
C4' C3' C14' C13' -1.0(5) . . . . ?
C4' C3' C14' C15' -177.7(2) . . . . ?
C4' C5' C6' C7' 0.3(5) . . . . ?
C4' C5' O1' C1' 1.5(4) . . . . ?
C5' C4' C9' C8' -0.9(4) . . . . ?
C5' C6' C7' C8' -1.6(5) . . . . ?
C6' C5' O1' C1' -179.4(3) . . . . ?
C6' C7' C8' C9' 1.5(5) . . . . ?
C7' C8' C9' C4' -0.3(5) . . . . ?
C9' C4' C5' C6' 0.9(4) . . . . ?
C9' C4' C5' O1' 180.0(2) . . . . ?
C10' C11' C12' C13' -0.4(5) . . . . ?
C10' C15' C16' C2' -175.4(2) . . . . ?
C10' C15' C16' C17' -53.7(3) . . . . ?
C10' C15' C16' C18' 67.1(3) . . . . ?
C11' C10' C15' C14' 0.3(4) . . . . ?
C11' C10' C15' C16' 179.6(2) . . . . ?
C11' C12' C13' C14' 0.5(4) . . . . ?
C12' C13' C14' C3' -176.6(3) . . . . ?
C12' C13' C14' C15' -0.2(4) . . . . ?
C13' C14' C15' C10' -0.2(4) . . . . ?
C13' C14' C15' C16' -179.6(2) . . . . ?
C14' C3' C4' C5' 172.4(2) . . . . ?
C14' C3' C4' C9' -7.4(4) . . . . ?
C14' C15' C16' C2' 4.0(3) . . . . ?
C14' C15' C16' C17' 125.7(2) . . . . ?
C14' C15' C16' C18' -113.5(2) . . . . ?
C15' C10' C11' C12' 0.0(4) . . . . ?
C15' C10' C11' Cl1' -179.8(2) . . . . ?
C15' C16' C17' O3' 102.6(3) . . . . ?
C15' C16' C17' O4' -76.1(3) . . . . ?
C15' C16' C18' O5' -5.2(6) . . . . ?
C15' C16' C18' O5'A -50.5(9) . . . . ?
C15' C16' C18' O6' 155.8(4) . . . . ?
C15' C16' C18' O6'A -176.1(8) . . . . ?
C16' C2' C3' C4' -179.2(2) . . . . ?
C16' C2' C3' C14' 3.2(3) . . . . ?
C16' C17' O4' C19' 179.6(2) . . . . ?
C16' C18' O6' C21' 176.9(9) . . . . ?
C16' C18' O6'A C1A -160(2) . . . . ?
C17' C16' C18' O5' 117.7(6) . . . . ?
C17' C16' C18' O5'A 72.3(9) . . . . ?
C17' C16' C18' O6' -81.4(4) . . . . ?
C17' C16' C18' O6'A -53.3(8) . . . . ?
C18' C16' C17' O3' -19.2(4) . . . . ?
C18' C16' C17' O4' 162.2(2) . . . . ?
C20' C19' O4' C17' 90.7(4) . . . . ?
C22' C21' O6' C18' -77.2(16) . . . . ?
Cl1' C11' C12' C13' 179.4(2) . . . . ?
O1' C1' C2' C3' -5.8(4) . . . . ?
O1' C1' C2' C16' -178.1(2) . . . . ?
O1' C5' C6' C7' -178.8(3) . . . . ?
O2' C1' C2' C3' 171.0(3) . . . . ?
O2' C1' C2' C16' -1.3(5) . . . . ?
O2' C1' O1' C5' -176.0(3) . . . . ?
O3' C17' O4' C19' 1.0(5) . . . . ?
O5' C18' O6' C21' -20.8(12) . . . . ?
O5'A C18' O6'A C1A 77(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
