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

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

data_adjp390
_database_code_depnum_ccdc_archive 'CCDC 1944706'
loop_
_audit_author_name
_audit_author_address
'zhen he'
;School of chemistry university of manchester
United Kingdom
;
_audit_update_record             
;
2019-08-01 deposited with the CCDC.	2020-01-20 downloaded from the CCDC.
;
_audit_creation_date             2019-05-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H18 O3'
_chemical_formula_sum            'C24 H18 O3'
_chemical_formula_weight         354.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   21.6130(13)
_cell_length_b                   12.1859(7)
_cell_length_c                   13.5922(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.043(6)
_cell_angle_gamma                90
_cell_volume                     3472.8(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3347
_cell_measurement_temperature    150.0(3)
_cell_measurement_theta_max      28.5360
_cell_measurement_theta_min      3.3280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7900
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.958
_diffrn_reflns_theta_min         3.226
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00   1.00   1.00    8.56    --  -18.77 -57.00 -30.00   31
  2  ω    -40.00  52.00   1.00    8.56    --  -18.77  38.00 120.00   92
  3  ω    -15.00  25.00   1.00    8.56    --  -18.77 -99.00  90.00   40
  4  ω    -38.00  38.00   1.00    8.56    --   20.02 -77.00 -60.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0179729000
_diffrn_orient_matrix_UB_12      0.0417694000
_diffrn_orient_matrix_UB_13      -0.0164524000
_diffrn_orient_matrix_UB_21      -0.0201451000
_diffrn_orient_matrix_UB_22      0.0403335000
_diffrn_orient_matrix_UB_23      0.0134652000
_diffrn_orient_matrix_UB_31      0.0204069000
_diffrn_orient_matrix_UB_32      0.0029469000
_diffrn_orient_matrix_UB_33      0.0494646000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3099
_reflns_number_total             3970
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3970
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.071
_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)+(0.0442P)²+3.8614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1351
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C6(H6), C18(H18), C10(H10), C14(H14), C9(H9), C22(H22), C12(H12),
 C5(H5), C16(H16), C13(H13)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C24(H24A,H24B,H24C)
2.c Idealised tetrahedral OH refined as rotating group:
 O27(H27)
;
_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
O27 O 0.41988(7) 0.98465(11) 0.07452(9) 0.0345(3) Uani 1 1 d . . . . .
H27 H 0.4332 1.0444 0.0611 0.052 Uiso 1 1 calc GR . . . .
O23 O 0.42728(6) 1.07353(11) -0.09928(9) 0.0336(3) Uani 1 1 d . . . . .
C2 C 0.37232(9) 0.61929(14) -0.51400(12) 0.0266(4) Uani 1 1 d . . . . .
C8 C 0.36328(8) 0.71588(14) -0.35753(12) 0.0246(4) Uani 1 1 d . . . . .
O25 O 0.37005(8) 0.78549(11) 0.08465(9) 0.0412(4) Uani 1 1 d . . . . .
C3 C 0.33521(8) 0.64998(13) -0.44423(12) 0.0246(4) Uani 1 1 d . . . . .
C7 C 0.32631(8) 0.74303(14) -0.28785(12) 0.0253(4) Uani 1 1 d . . . . .
C4 C 0.27080(9) 0.61392(14) -0.46128(13) 0.0283(4) Uani 1 1 d . . . . .
C20 C 0.39872(8) 0.92541(15) -0.01347(12) 0.0276(4) Uani 1 1 d . . . . .
C21 C 0.37193(9) 0.82204(15) -0.01010(12) 0.0295(4) Uani 1 1 d . . . . .
C15 C 0.27839(10) 0.52294(15) -0.61681(14) 0.0355(4) Uani 1 1 d . . . . .
H15 H 0.2593 0.4829 -0.6744 0.043 Uiso 1 1 calc R . . . .
C11 C 0.43727(9) 0.65169(16) -0.49654(13) 0.0319(4) Uani 1 1 d . . . . .
C6 C 0.26299(9) 0.70579(15) -0.30698(13) 0.0296(4) Uani 1 1 d . . . . .
H6 H 0.2386 0.7237 -0.2615 0.036 Uiso 1 1 calc R . . . .
C18 C 0.37931(8) 0.91188(15) -0.19675(12) 0.0263(4) Uani 1 1 d . . . . .
H18 H 0.3820 0.9422 -0.2584 0.032 Uiso 1 1 calc R . . . .
C1 C 0.34418(9) 0.55457(15) -0.60093(13) 0.0310(4) Uani 1 1 d . . . . .
C10 C 0.46399(9) 0.71791(17) -0.40951(14) 0.0363(4) Uani 1 1 d . . . . .
H10 H 0.5062 0.7409 -0.3977 0.044 Uiso 1 1 calc R . . . .
C17 C 0.35259(8) 0.80773(14) -0.19370(12) 0.0263(4) Uani 1 1 d . . . . .
C14 C 0.38198(11) 0.52238(16) -0.66642(14) 0.0399(5) Uani 1 1 d . . . . .
H14 H 0.3641 0.4806 -0.7235 0.048 Uiso 1 1 calc R . . . .
C9 C 0.42876(8) 0.74717(15) -0.34477(13) 0.0295(4) Uani 1 1 d . . . . .
H9 H 0.4478 0.7898 -0.2889 0.035 Uiso 1 1 calc R . . . .
C22 C 0.34873(9) 0.76357(15) -0.09987(13) 0.0297(4) Uani 1 1 d . . . . .
H22 H 0.3305 0.6947 -0.0975 0.036 Uiso 1 1 calc R . . . .
C19 C 0.40180(8) 0.96974(14) -0.10709(12) 0.0264(4) Uani 1 1 d . . . . .
C12 C 0.47329(10) 0.61654(18) -0.56402(16) 0.0417(5) Uani 1 1 d . . . . .
H12 H 0.5159 0.6366 -0.5530 0.050 Uiso 1 1 calc R . . . .
C5 C 0.23581(9) 0.64349(15) -0.39119(14) 0.0310(4) Uani 1 1 d . . . . .
H5 H 0.1936 0.6208 -0.4015 0.037 Uiso 1 1 calc R . . . .
C16 C 0.24371(9) 0.54993(15) -0.55016(14) 0.0332(4) Uani 1 1 d . . . . .
H16 H 0.2016 0.5267 -0.5619 0.040 Uiso 1 1 calc R . . . .
C13 C 0.44538(11) 0.55194(18) -0.64710(16) 0.0455(5) Uani 1 1 d . . . . .
H13 H 0.4699 0.5282 -0.6905 0.055 Uiso 1 1 calc R . . . .
C26 C 0.34019(11) 0.68208(17) 0.09073(15) 0.0425(5) Uani 1 1 d . . . . .
H26A H 0.2966 0.6850 0.0524 0.064 Uiso 1 1 calc GR . . . .
H26B H 0.3415 0.6658 0.1603 0.064 Uiso 1 1 calc GR . . . .
H26C H 0.3624 0.6258 0.0636 0.064 Uiso 1 1 calc GR . . . .
C24 C 0.42617(12) 1.12885(19) -0.19254(15) 0.0499(6) Uani 1 1 d . . . . .
H24A H 0.4503 1.0874 -0.2305 0.075 Uiso 1 1 calc GR . . . .
H24B H 0.4446 1.2005 -0.1783 0.075 Uiso 1 1 calc GR . . . .
H24C H 0.3829 1.1357 -0.2314 0.075 Uiso 1 1 calc GR . . . .


_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
O27 C20 1.377(2) . ?
O23 C19 1.373(2) . ?
O23 C24 1.431(2) . ?
C2 C3 1.432(2) . ?
C2 C11 1.422(3) . ?
C2 C1 1.428(2) . ?
C8 C3 1.433(2) . ?
C8 C7 1.418(2) . ?
C8 C9 1.435(2) . ?
O25 C21 1.373(2) . ?
O25 C26 1.427(2) . ?
C3 C4 1.424(2) . ?
C7 C6 1.405(2) . ?
C7 C17 1.493(2) . ?
C4 C5 1.400(2) . ?
C4 C16 1.438(2) . ?
C20 C21 1.392(3) . ?
C20 C19 1.399(2) . ?
C21 C22 1.397(2) . ?
C15 C1 1.438(3) . ?
C15 C16 1.349(3) . ?
C11 C10 1.433(3) . ?
C11 C12 1.406(3) . ?
C6 C5 1.380(3) . ?
C18 C17 1.399(2) . ?
C18 C19 1.390(2) . ?
C1 C14 1.402(3) . ?
C10 C9 1.344(3) . ?
C17 C22 1.405(2) . ?
C14 C13 1.379(3) . ?
C12 C13 1.389(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O23 C24 116.44(14) . . ?
C11 C2 C3 120.39(16) . . ?
C11 C2 C1 119.77(16) . . ?
C1 C2 C3 119.83(17) . . ?
C3 C8 C9 117.15(15) . . ?
C7 C8 C3 119.02(16) . . ?
C7 C8 C9 123.79(15) . . ?
C21 O25 C26 117.23(14) . . ?
C2 C3 C8 119.82(16) . . ?
C4 C3 C2 119.60(16) . . ?
C4 C3 C8 120.57(15) . . ?
C8 C7 C17 122.47(16) . . ?
C6 C7 C8 118.84(16) . . ?
C6 C7 C17 118.68(15) . . ?
C3 C4 C16 119.13(16) . . ?
C5 C4 C3 118.56(16) . . ?
C5 C4 C16 122.31(17) . . ?
O27 C20 C21 119.94(15) . . ?
O27 C20 C19 120.58(16) . . ?
C21 C20 C19 119.44(15) . . ?
O25 C21 C20 115.59(15) . . ?
O25 C21 C22 124.61(17) . . ?
C20 C21 C22 119.80(15) . . ?
C16 C15 C1 121.60(17) . . ?
C2 C11 C10 118.56(16) . . ?
C12 C11 C2 119.15(18) . . ?
C12 C11 C10 122.29(19) . . ?
C5 C6 C7 122.04(16) . . ?
C19 C18 C17 119.57(15) . . ?
C2 C1 C15 118.64(16) . . ?
C14 C1 C2 118.87(19) . . ?
C14 C1 C15 122.47(18) . . ?
C9 C10 C11 120.74(18) . . ?
C18 C17 C7 121.84(15) . . ?
C18 C17 C22 119.34(16) . . ?
C22 C17 C7 118.79(16) . . ?
C13 C14 C1 120.74(19) . . ?
C10 C9 C8 123.32(17) . . ?
C21 C22 C17 120.64(17) . . ?
O23 C19 C20 113.08(15) . . ?
O23 C19 C18 125.70(15) . . ?
C18 C19 C20 121.20(16) . . ?
C13 C12 C11 120.2(2) . . ?
C6 C5 C4 120.97(17) . . ?
C15 C16 C4 121.14(18) . . ?
C14 C13 C12 121.22(18) . . ?

_olex2_date_sample_data_collection 2019-05-25
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.489
_oxdiff_exptl_absorpt_empirical_full_min 0.760
####################################################################### 
# 
# 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_adjp398
_database_code_depnum_ccdc_archive 'CCDC 1944709'
loop_
_audit_author_name
_audit_author_address
'zhen he'
;School of chemistry university of manchester
United Kingdom
;
_audit_update_record             
;
2019-08-01 deposited with the CCDC.	2020-01-20 downloaded from the CCDC.
;
_audit_creation_date             2019-07-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C26 H24 O6'
_chemical_formula_sum            'C26 H24 O6'
_chemical_formula_weight         432.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   14.145(2)
_cell_length_b                   7.4410(10)
_cell_length_c                   24.560(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.170(13)
_cell_angle_gamma                90
_cell_volume                     2570.0(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1954
_cell_measurement_temperature    149.9(3)
_cell_measurement_theta_max      21.5180
_cell_measurement_theta_min      3.0950
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.118
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1094
_diffrn_reflns_av_unetI/netI     0.1331
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            14362
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.862
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  25.00   1.00   41.55    --  -18.77 -99.00  60.00   45
  2  ω    -20.00  25.00   1.00   41.55    --  -18.77 -99.00-180.00   45
  3  ω     -7.00  93.00   1.00   41.55    --   20.02  38.00 150.00  100
  4  ω     -7.00  93.00   1.00   41.55    --   20.02  38.00  60.00  100
  5  ω     35.00  98.00   1.00   41.55    --   20.02 178.00 150.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0193536000
_diffrn_orient_matrix_UB_12      -0.0089217000
_diffrn_orient_matrix_UB_13      0.0253537000
_diffrn_orient_matrix_UB_21      -0.0465262000
_diffrn_orient_matrix_UB_22      0.0027429000
_diffrn_orient_matrix_UB_23      -0.0139217000
_diffrn_orient_matrix_UB_31      0.0003894000
_diffrn_orient_matrix_UB_32      -0.0949102000
_diffrn_orient_matrix_UB_33      -0.0027810000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2218
_reflns_number_total             4517
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4517
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1401
_refine_ls_R_factor_gt           0.0709
_refine_ls_restrained_S_all      0.975
_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)+(0.0518P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1760
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C00D(H00D), C00F(H00F), C00G(H00G), C00K(H00K), C00L(H00L),
 C00P(H00P), C00Q(H00Q), C00T(H00T), C00U(H00U)
2.b Idealised Me refined as rotating group:
 C00O(H00A,H00B,H00C), C00R(H00E,H00H,H00I), C00V(H00J,H00M,H00N), C00W(H00O,
 H00R,H00S)
2.c Idealised tetrahedral OH refined as rotating group:
 O002(H002), O006(H006)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.53645(17) 0.4007(3) 0.74337(10) 0.0449(7) Uani 1 1 d . . . . .
O002 O 0.15152(16) 0.4782(4) 0.68175(10) 0.0426(7) Uani 1 1 d . . . . .
H002 H 0.1206 0.4596 0.7076 0.064 Uiso 1 1 calc GR . . . .
O003 O 0.11103(18) 0.3861(3) 0.78378(10) 0.0487(7) Uani 1 1 d . . . . .
O004 O 0.23746(19) 1.0445(3) 0.86699(10) 0.0512(8) Uani 1 1 d . . . . .
O005 O 0.08627(19) 0.9145(3) 0.89927(10) 0.0508(8) Uani 1 1 d . . . . .
O006 O 0.1551(2) 0.2382(3) 0.44407(11) 0.0621(9) Uani 1 1 d . . . . .
H006 H 0.1599 0.3245 0.4238 0.093 Uiso 1 1 calc GR . . . .
C007 C 0.3817(3) 0.4965(4) 0.76724(15) 0.0335(9) Uani 1 1 d . . . . .
H007 H 0.4070 0.5261 0.8026 0.040 Uiso 1 1 calc R . . . .
C008 C 0.2476(2) 0.4635(4) 0.69922(15) 0.0328(9) Uani 1 1 d . . . . .
C009 C 0.2262(2) 0.6141(4) 0.78938(14) 0.0320(9) Uani 1 1 d . . . . .
C00A C 0.2840(2) 0.5202(4) 0.75159(14) 0.0324(9) Uani 1 1 d . . . . .
C00B C 0.4402(3) 0.4301(4) 0.73085(15) 0.0355(9) Uani 1 1 d . . . . .
C00C C 0.2212(2) 0.1896(5) 0.59174(15) 0.0340(9) Uani 1 1 d . . . . .
C00D C 0.2583(3) 0.7817(5) 0.80945(14) 0.0362(9) Uani 1 1 d . . . . .
H00D H 0.3139 0.8290 0.7983 0.043 Uiso 1 1 calc R . . . .
C00E C 0.3065(2) 0.4029(4) 0.66097(14) 0.0324(9) Uani 1 1 d . . . . .
C00F C 0.4028(3) 0.3876(4) 0.67807(15) 0.0372(9) Uani 1 1 d . . . . .
H00F H 0.4435 0.3475 0.6533 0.045 Uiso 1 1 calc R . . . .
C00G C 0.0923(3) 0.6447(5) 0.84303(14) 0.0386(10) Uani 1 1 d . . . . .
H00G H 0.0369 0.5974 0.8546 0.046 Uiso 1 1 calc R . . . .
C00H C 0.1415(3) 0.5500(5) 0.80584(14) 0.0360(9) Uani 1 1 d . . . . .
C00I C 0.1850(3) 0.1508(5) 0.53738(15) 0.0370(9) Uani 1 1 d . . . . .
C00J C 0.2681(2) 0.3574(5) 0.60433(14) 0.0334(9) Uani 1 1 d . . . . .
C00K C 0.2108(2) 0.0581(5) 0.63240(15) 0.0386(10) Uani 1 1 d . . . . .
H00K H 0.2346 0.0807 0.6685 0.046 Uiso 1 1 calc R . . . .
C00L C 0.2747(3) 0.4757(5) 0.56269(15) 0.0431(10) Uani 1 1 d . . . . .
H00L H 0.3044 0.5855 0.5707 0.052 Uiso 1 1 calc R . . . .
C00M C 0.2099(3) 0.8783(5) 0.84518(14) 0.0391(10) Uani 1 1 d . . . . .
C00N C 0.1263(3) 0.8086(5) 0.86236(15) 0.0409(10) Uani 1 1 d . . . . .
C00O C 0.0031(3) 0.8496(5) 0.92116(15) 0.0474(11) Uani 1 1 d . . . . .
H00A H -0.0482 0.8409 0.8924 0.071 Uiso 1 1 calc GR . . . .
H00B H -0.0141 0.9311 0.9487 0.071 Uiso 1 1 calc GR . . . .
H00C H 0.0158 0.7331 0.9371 0.071 Uiso 1 1 calc GR . . . .
C00P C 0.2389(3) 0.4399(5) 0.50831(15) 0.0447(10) Uani 1 1 d . . . . .
H00P H 0.2460 0.5239 0.4810 0.054 Uiso 1 1 calc R . . . .
C00Q C 0.1659(3) -0.1030(5) 0.61913(18) 0.0494(11) Uani 1 1 d . . . . .
H00Q H 0.1596 -0.1884 0.6462 0.059 Uiso 1 1 calc R . . . .
C00R C 0.5703(3) 0.3891(5) 0.80003(15) 0.0507(11) Uani 1 1 d . . . . .
H00E H 0.6332 0.3388 0.8040 0.076 Uiso 1 1 calc GR . . . .
H00H H 0.5287 0.3136 0.8183 0.076 Uiso 1 1 calc GR . . . .
H00I H 0.5720 0.5070 0.8160 0.076 Uiso 1 1 calc GR . . . .
C00S C 0.1935(3) 0.2805(5) 0.49569(15) 0.0446(11) Uani 1 1 d . . . . .
C00T C 0.1299(3) -0.1371(5) 0.56512(18) 0.0541(12) Uani 1 1 d . . . . .
H00T H 0.0993 -0.2457 0.5565 0.065 Uiso 1 1 calc R . . . .
C00U C 0.1384(3) -0.0164(5) 0.52501(17) 0.0505(11) Uani 1 1 d . . . . .
H00U H 0.1138 -0.0423 0.4892 0.061 Uiso 1 1 calc R . . . .
C00V C 0.0315(3) 0.3008(5) 0.80436(16) 0.0579(12) Uani 1 1 d . . . . .
H00J H -0.0246 0.3720 0.7952 0.087 Uiso 1 1 calc GR . . . .
H00M H 0.0433 0.2897 0.8434 0.087 Uiso 1 1 calc GR . . . .
H00N H 0.0224 0.1837 0.7883 0.087 Uiso 1 1 calc GR . . . .
C00W C 0.3157(3) 1.1315(6) 0.84546(19) 0.0810(16) Uani 1 1 d . . . . .
H00O H 0.3035 1.1389 0.8063 0.121 Uiso 1 1 calc GR . . . .
H00R H 0.3727 1.0637 0.8551 0.121 Uiso 1 1 calc GR . . . .
H00S H 0.3233 1.2504 0.8605 0.121 Uiso 1 1 calc GR . . . .


_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
O001 C00B 1.381(4) . ?
O001 C00R 1.425(4) . ?
O002 H002 0.8200 . ?
O002 C008 1.384(4) . ?
O003 C00H 1.385(4) . ?
O003 C00V 1.431(4) . ?
O004 C00M 1.387(4) . ?
O004 C00W 1.431(5) . ?
O005 C00N 1.369(4) . ?
O005 C00O 1.428(4) . ?
O006 H006 0.8200 . ?
O006 C00S 1.361(4) . ?
C007 H007 0.9300 . ?
C007 C00A 1.405(4) . ?
C007 C00B 1.374(5) . ?
C008 C00A 1.398(4) . ?
C008 C00E 1.396(5) . ?
C009 C00A 1.477(5) . ?
C009 C00D 1.399(4) . ?
C009 C00H 1.389(5) . ?
C00B C00F 1.383(5) . ?
C00C C00I 1.407(4) . ?
C00C C00J 1.432(5) . ?
C00C C00K 1.417(5) . ?
C00D H00D 0.9300 . ?
C00D C00M 1.373(5) . ?
C00E C00F 1.387(4) . ?
C00E C00J 1.477(4) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00H 1.398(5) . ?
C00G C00N 1.377(5) . ?
C00I C00S 1.421(5) . ?
C00I C00U 1.426(5) . ?
C00J C00L 1.360(4) . ?
C00K H00K 0.9300 . ?
C00K C00Q 1.379(5) . ?
C00L H00L 0.9300 . ?
C00L C00P 1.402(5) . ?
C00M C00N 1.397(5) . ?
C00O H00A 0.9600 . ?
C00O H00B 0.9600 . ?
C00O H00C 0.9600 . ?
C00P H00P 0.9300 . ?
C00P C00S 1.368(5) . ?
C00Q H00Q 0.9300 . ?
C00Q C00T 1.392(5) . ?
C00R H00E 0.9600 . ?
C00R H00H 0.9600 . ?
C00R H00I 0.9600 . ?
C00T H00T 0.9300 . ?
C00T C00U 1.348(5) . ?
C00U H00U 0.9300 . ?
C00V H00J 0.9600 . ?
C00V H00M 0.9600 . ?
C00V H00N 0.9600 . ?
C00W H00O 0.9600 . ?
C00W H00R 0.9600 . ?
C00W H00S 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
C00B O001 C00R 116.6(3) . . ?
C008 O002 H002 109.5 . . ?
C00H O003 C00V 118.4(3) . . ?
C00M O004 C00W 117.2(3) . . ?
C00N O005 C00O 118.1(3) . . ?
C00S O006 H006 109.5 . . ?
C00A C007 H007 119.6 . . ?
C00B C007 H007 119.6 . . ?
C00B C007 C00A 120.7(3) . . ?
O002 C008 C00A 120.9(3) . . ?
O002 C008 C00E 117.0(3) . . ?
C00E C008 C00A 121.9(3) . . ?
C00D C009 C00A 117.6(3) . . ?
C00H C009 C00A 125.0(3) . . ?
C00H C009 C00D 117.4(3) . . ?
C007 C00A C009 118.8(3) . . ?
C008 C00A C007 117.9(3) . . ?
C008 C00A C009 123.2(3) . . ?
O001 C00B C00F 116.1(3) . . ?
C007 C00B O001 124.1(3) . . ?
C007 C00B C00F 119.8(3) . . ?
C00I C00C C00J 119.8(3) . . ?
C00I C00C C00K 118.2(3) . . ?
C00K C00C C00J 122.1(3) . . ?
C009 C00D H00D 119.1 . . ?
C00M C00D C009 121.8(4) . . ?
C00M C00D H00D 119.1 . . ?
C008 C00E C00J 121.5(3) . . ?
C00F C00E C008 117.5(3) . . ?
C00F C00E C00J 121.1(3) . . ?
C00B C00F C00E 121.9(3) . . ?
C00B C00F H00F 119.0 . . ?
C00E C00F H00F 119.0 . . ?
C00H C00G H00G 120.3 . . ?
C00N C00G H00G 120.3 . . ?
C00N C00G C00H 119.4(3) . . ?
O003 C00H C009 115.5(3) . . ?
O003 C00H C00G 122.9(3) . . ?
C009 C00H C00G 121.6(3) . . ?
C00C C00I C00S 119.6(3) . . ?
C00C C00I C00U 119.6(3) . . ?
C00S C00I C00U 120.8(3) . . ?
C00C C00J C00E 121.2(3) . . ?
C00L C00J C00C 118.0(3) . . ?
C00L C00J C00E 120.7(3) . . ?
C00C C00K H00K 119.5 . . ?
C00Q C00K C00C 120.9(3) . . ?
C00Q C00K H00K 119.5 . . ?
C00J C00L H00L 118.4 . . ?
C00J C00L C00P 123.1(3) . . ?
C00P C00L H00L 118.4 . . ?
O004 C00M C00N 115.2(3) . . ?
C00D C00M O004 125.1(3) . . ?
C00D C00M C00N 119.7(3) . . ?
O005 C00N C00G 125.7(4) . . ?
O005 C00N C00M 114.2(3) . . ?
C00G C00N C00M 120.0(3) . . ?
O005 C00O H00A 109.5 . . ?
O005 C00O H00B 109.5 . . ?
O005 C00O H00C 109.5 . . ?
H00A C00O H00B 109.5 . . ?
H00A C00O H00C 109.5 . . ?
H00B C00O H00C 109.5 . . ?
C00L C00P H00P 120.2 . . ?
C00S C00P C00L 119.5(4) . . ?
C00S C00P H00P 120.2 . . ?
C00K C00Q H00Q 120.1 . . ?
C00K C00Q C00T 119.7(4) . . ?
C00T C00Q H00Q 120.1 . . ?
O001 C00R H00E 109.5 . . ?
O001 C00R H00H 109.5 . . ?
O001 C00R H00I 109.5 . . ?
H00E C00R H00H 109.5 . . ?
H00E C00R H00I 109.5 . . ?
H00H C00R H00I 109.5 . . ?
O006 C00S C00I 117.2(3) . . ?
O006 C00S C00P 122.8(4) . . ?
C00P C00S C00I 119.9(3) . . ?
C00Q C00T H00T 119.2 . . ?
C00U C00T C00Q 121.5(4) . . ?
C00U C00T H00T 119.2 . . ?
C00I C00U H00U 120.0 . . ?
C00T C00U C00I 120.1(4) . . ?
C00T C00U H00U 120.0 . . ?
O003 C00V H00J 109.5 . . ?
O003 C00V H00M 109.5 . . ?
O003 C00V H00N 109.5 . . ?
H00J C00V H00M 109.5 . . ?
H00J C00V H00N 109.5 . . ?
H00M C00V H00N 109.5 . . ?
O004 C00W H00O 109.5 . . ?
O004 C00W H00R 109.5 . . ?
O004 C00W H00S 109.5 . . ?
H00O C00W H00R 109.5 . . ?
H00O C00W H00S 109.5 . . ?
H00R C00W H00S 109.5 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.500 -0.626 0.500 270.6 56.9 ?
2 0.500 -0.067 1.000 270.6 56.9 ?


_olex2_date_sample_data_collection 2019-06-30
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.307
_oxdiff_exptl_absorpt_empirical_full_min 0.563
####################################################################### 
# 
# 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_adjp399
_database_code_depnum_ccdc_archive 'CCDC 1944710'
loop_
_audit_author_name
_audit_author_address
'zhen he'
;School of chemistry university of manchester
United Kingdom
;
_audit_update_record             
;
2019-08-01 deposited with the CCDC.	2020-01-20 downloaded from the CCDC.
;
_audit_creation_date             2019-07-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H15 Cl O3'
_chemical_formula_sum            'C22 H15 Cl O3'
_chemical_formula_weight         362.79
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   16.2589(10)
_cell_length_b                   6.7715(3)
_cell_length_c                   16.4568(9)
_cell_angle_alpha                90
_cell_angle_beta                 106.511(6)
_cell_angle_gamma                90
_cell_volume                     1737.13(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3550
_cell_measurement_temperature    149.9(3)
_cell_measurement_theta_max      28.3940
_cell_measurement_theta_min      3.0960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68234
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11809
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.988
_diffrn_reflns_theta_min         3.108
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  25.00   1.00    1.76    --  -18.77 -99.00 -90.00   45
  2  ω    -20.00  64.00   1.00    1.76    --   20.02 -99.00-180.00   84
  3  ω    -53.00  47.00   1.00    1.76    --   20.02 -38.00  90.00  100
  4  ω     -7.00  93.00   1.00    1.76    --   20.02  38.00 -90.00  100
  5  ω    -29.00   2.00   1.00    1.76    --   20.02  19.00-180.00   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0417484000
_diffrn_orient_matrix_UB_12      0.0056870000
_diffrn_orient_matrix_UB_13      -0.0052636000
_diffrn_orient_matrix_UB_21      -0.0181610000
_diffrn_orient_matrix_UB_22      0.0108233000
_diffrn_orient_matrix_UB_23      -0.0443816000
_diffrn_orient_matrix_UB_31      -0.0003996000
_diffrn_orient_matrix_UB_32      0.1039901000
_diffrn_orient_matrix_UB_33      0.0049177000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2977
_reflns_number_total             4055
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4055
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0521
_refine_ls_restrained_S_all      1.053
_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)+(0.0380P)²+0.7708P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1222
_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:
 C006(H006), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00Q(H00Q)
2.b Idealised Me refined as rotating group:
 C00P(H00A,H00B,H00C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl01 Cl 0.45952(4) 0.24423(8) 0.27565(4) 0.03399(17) Uani 1 1 d . . . . .
O002 O 0.33787(9) 0.29126(19) 0.38723(9) 0.0222(3) Uani 1 1 d . . . . .
O003 O 0.67614(9) 0.2064(2) 0.56412(10) 0.0298(4) Uani 1 1 d . . . . .
O004 O 0.40398(10) 0.3297(3) 0.67597(10) 0.0413(4) Uani 1 1 d . . . . .
C005 C 0.29998(13) 0.3027(3) 0.45218(13) 0.0215(4) Uani 1 1 d . . . . .
C006 C 0.52694(13) 0.2438(3) 0.56406(14) 0.0212(4) Uani 1 1 d . . . . .
H006 H 0.5401 0.2407 0.6229 0.025 Uiso 1 1 calc R . . . .
C007 C 0.44246(13) 0.2657(3) 0.51343(13) 0.0197(4) Uani 1 1 d . . . . .
C008 C 0.48749(13) 0.2484(3) 0.38510(13) 0.0212(4) Uani 1 1 d . . . . .
C009 C 0.35922(13) 0.2837(3) 0.52937(13) 0.0214(4) Uani 1 1 d . . . . .
C00A C 0.20731(13) 0.3381(3) 0.42400(13) 0.0218(4) Uani 1 1 d . . . . .
C00B C 0.26194(13) 0.2124(3) 0.62459(13) 0.0234(4) Uani 1 1 d . . . . .
C00C C 0.34606(13) 0.2790(3) 0.61435(13) 0.0239(4) Uani 1 1 d . . . . .
C00D C 0.42455(13) 0.2678(3) 0.42613(13) 0.0205(4) Uani 1 1 d . . . . .
C00E C 0.16928(13) 0.4780(3) 0.46380(13) 0.0255(5) Uani 1 1 d . . . . .
H00E H 0.2031 0.5558 0.5071 0.031 Uiso 1 1 calc R . . . .
C00F C 0.23167(14) 0.3048(3) 0.68607(14) 0.0278(5) Uani 1 1 d . . . . .
H00F H 0.2648 0.4006 0.7210 0.033 Uiso 1 1 calc R . . . .
C00G C 0.57115(13) 0.2290(3) 0.43437(14) 0.0243(5) Uani 1 1 d . . . . .
H00G H 0.6151 0.2171 0.4088 0.029 Uiso 1 1 calc R . . . .
C00H C 0.06782(15) 0.2520(3) 0.33273(15) 0.0312(5) Uani 1 1 d . . . . .
H00H H 0.0339 0.1769 0.2885 0.037 Uiso 1 1 calc R . . . .
C00I C 0.59030(13) 0.2271(3) 0.52309(14) 0.0233(5) Uani 1 1 d . . . . .
C00J C 0.21390(14) 0.0627(3) 0.57519(14) 0.0272(5) Uani 1 1 d . . . . .
H00J H 0.2343 -0.0021 0.5350 0.033 Uiso 1 1 calc R . . . .
C00K C 0.15586(14) 0.2278(3) 0.35744(13) 0.0262(5) Uani 1 1 d . . . . .
H00K H 0.1809 0.1371 0.3293 0.031 Uiso 1 1 calc R . . . .
C00L C 0.08081(14) 0.5012(3) 0.43866(15) 0.0318(5) Uani 1 1 d . . . . .
H00L H 0.0554 0.5937 0.4656 0.038 Uiso 1 1 calc R . . . .
C00M C 0.03027(14) 0.3873(3) 0.37365(15) 0.0325(5) Uani 1 1 d . . . . .
H00M H -0.0290 0.4020 0.3576 0.039 Uiso 1 1 calc R . . . .
C00N C 0.13532(15) 0.0111(3) 0.58649(15) 0.0341(5) Uani 1 1 d . . . . .
H00N H 0.1032 -0.0898 0.5541 0.041 Uiso 1 1 calc R . . . .
C00O C 0.15241(15) 0.2544(3) 0.69520(15) 0.0325(5) Uani 1 1 d . . . . .
H00O H 0.1314 0.3192 0.7350 0.039 Uiso 1 1 calc R . . . .
C00P C 0.70147(14) 0.2196(3) 0.65432(15) 0.0311(5) Uani 1 1 d . . . . .
H00A H 0.6820 0.3427 0.6712 0.047 Uiso 1 1 calc GR . . . .
H00B H 0.7629 0.2129 0.6752 0.047 Uiso 1 1 calc GR . . . .
H00C H 0.6767 0.1122 0.6773 0.047 Uiso 1 1 calc GR . . . .
C00Q C 0.10449(15) 0.1083(3) 0.64544(16) 0.0369(6) Uani 1 1 d . . . . .
H00Q H 0.0511 0.0750 0.6516 0.044 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl01 C008 1.728(2) . ?
O002 C005 1.379(2) . ?
O002 C00D 1.381(2) . ?
O003 C00I 1.374(3) . ?
O003 C00P 1.426(3) . ?
O004 C00C 1.221(3) . ?
C005 C009 1.365(3) . ?
C005 C00A 1.465(3) . ?
C006 H006 0.9300 . ?
C006 C007 1.397(3) . ?
C006 C00I 1.387(3) . ?
C007 C009 1.455(3) . ?
C007 C00D 1.383(3) . ?
C008 C00D 1.383(3) . ?
C008 C00G 1.378(3) . ?
C009 C00C 1.474(3) . ?
C00A C00E 1.392(3) . ?
C00A C00K 1.392(3) . ?
C00B C00C 1.494(3) . ?
C00B C00F 1.393(3) . ?
C00B C00J 1.392(3) . ?
C00E H00E 0.9300 . ?
C00E C00L 1.388(3) . ?
C00F H00F 0.9300 . ?
C00F C00O 1.382(3) . ?
C00G H00G 0.9300 . ?
C00G C00I 1.404(3) . ?
C00H H00H 0.9300 . ?
C00H C00K 1.382(3) . ?
C00H C00M 1.378(3) . ?
C00J H00J 0.9300 . ?
C00J C00N 1.387(3) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00L C00M 1.384(3) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00N C00Q 1.379(3) . ?
C00O H00O 0.9300 . ?
C00O C00Q 1.376(3) . ?
C00P H00A 0.9600 . ?
C00P H00B 0.9600 . ?
C00P H00C 0.9600 . ?
C00Q H00Q 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
C005 O002 C00D 105.59(16) . . ?
C00I O003 C00P 117.24(16) . . ?
O002 C005 C00A 114.18(18) . . ?
C009 C005 O002 111.32(17) . . ?
C009 C005 C00A 134.46(18) . . ?
C007 C006 H006 121.3 . . ?
C00I C006 H006 121.3 . . ?
C00I C006 C007 117.3(2) . . ?
C006 C007 C009 135.11(19) . . ?
C00D C007 C006 120.12(18) . . ?
C00D C007 C009 104.74(18) . . ?
C00D C008 Cl01 119.88(17) . . ?
C00G C008 Cl01 122.36(15) . . ?
C00G C008 C00D 117.74(19) . . ?
C005 C009 C007 106.66(18) . . ?
C005 C009 C00C 129.11(18) . . ?
C007 C009 C00C 124.23(19) . . ?
C00E C00A C005 121.13(19) . . ?
C00K C00A C005 119.69(18) . . ?
C00K C00A C00E 119.16(19) . . ?
C00F C00B C00C 118.04(19) . . ?
C00J C00B C00C 122.23(18) . . ?
C00J C00B C00F 119.7(2) . . ?
O004 C00C C009 119.75(19) . . ?
O004 C00C C00B 120.38(19) . . ?
C009 C00C C00B 119.86(18) . . ?
O002 C00D C007 111.63(16) . . ?
O002 C00D C008 125.71(19) . . ?
C007 C00D C008 122.67(19) . . ?
C00A C00E H00E 120.1 . . ?
C00L C00E C00A 119.9(2) . . ?
C00L C00E H00E 120.1 . . ?
C00B C00F H00F 120.0 . . ?
C00O C00F C00B 120.1(2) . . ?
C00O C00F H00F 120.0 . . ?
C008 C00G H00G 119.9 . . ?
C008 C00G C00I 120.21(18) . . ?
C00I C00G H00G 119.9 . . ?
C00K C00H H00H 120.0 . . ?
C00M C00H H00H 120.0 . . ?
C00M C00H C00K 120.0(2) . . ?
O003 C00I C006 124.1(2) . . ?
O003 C00I C00G 113.97(17) . . ?
C006 C00I C00G 121.9(2) . . ?
C00B C00J H00J 120.3 . . ?
C00N C00J C00B 119.4(2) . . ?
C00N C00J H00J 120.3 . . ?
C00A C00K H00K 119.7 . . ?
C00H C00K C00A 120.6(2) . . ?
C00H C00K H00K 119.7 . . ?
C00E C00L H00L 119.8 . . ?
C00M C00L C00E 120.3(2) . . ?
C00M C00L H00L 119.8 . . ?
C00H C00M C00L 120.0(2) . . ?
C00H C00M H00M 120.0 . . ?
C00L C00M H00M 120.0 . . ?
C00J C00N H00N 119.8 . . ?
C00Q C00N C00J 120.4(2) . . ?
C00Q C00N H00N 119.8 . . ?
C00F C00O H00O 120.0 . . ?
C00Q C00O C00F 120.0(2) . . ?
C00Q C00O H00O 120.0 . . ?
O003 C00P H00A 109.5 . . ?
O003 C00P H00B 109.5 . . ?
O003 C00P H00C 109.5 . . ?
H00A C00P H00B 109.5 . . ?
H00A C00P H00C 109.5 . . ?
H00B C00P H00C 109.5 . . ?
C00N C00Q H00Q 119.9 . . ?
C00O C00Q C00N 120.3(2) . . ?
C00O C00Q H00Q 119.9 . . ?

_olex2_date_sample_data_collection 2019-07-06
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.340
_oxdiff_exptl_absorpt_empirical_full_min 0.597
####################################################################### 
# 
# 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_adjp394
_database_code_depnum_ccdc_archive 'CCDC 1944708'
loop_
_audit_author_name
_audit_author_address
'zhen he'
;School of chemistry university of manchester
United Kingdom
;
_audit_update_record             
;
2019-08-01 deposited with the CCDC.	2020-01-20 downloaded from the CCDC.
;
_audit_creation_date             2019-06-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H24 O7'
_chemical_formula_sum            'C25 H24 O7'
_chemical_formula_weight         436.44
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   12.5579(10)
_cell_length_b                   5.2167(4)
_cell_length_c                   35.021(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.917(7)
_cell_angle_gamma                90
_cell_volume                     2285.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1921
_cell_measurement_temperature    150.0(3)
_cell_measurement_theta_max      26.2270
_cell_measurement_theta_min      3.2490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.1206
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            11165
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.096
_diffrn_reflns_theta_min         3.218
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00 -28.90   0.30   11.10    --  -18.77 -57.00  60.00  167
  2  ω    -14.00  25.00   0.30   11.10    --  -18.77 -99.00 -90.00  130
  3  ω    -85.00 -59.20   0.30   11.10    --  -18.77 -19.00-150.00   86
  4  ω    -34.00  24.20   0.30   11.10    --  -18.77 -19.00-150.00  194
  5  ω    -36.00  52.20   0.30   11.10    --  -18.77  77.00-180.00  294
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0556222000
_diffrn_orient_matrix_UB_12      -0.0154779000
_diffrn_orient_matrix_UB_13      -0.0049490000
_diffrn_orient_matrix_UB_21      0.0091776000
_diffrn_orient_matrix_UB_22      -0.0007660000
_diffrn_orient_matrix_UB_23      -0.0197048000
_diffrn_orient_matrix_UB_31      0.0063364000
_diffrn_orient_matrix_UB_32      -0.1349879000
_diffrn_orient_matrix_UB_33      0.0006843000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3169
_reflns_number_total             5341
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.111
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1549
_refine_ls_R_factor_gt           0.0968
_refine_ls_restrained_S_all      1.083
_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)+(0.0730P)²+2.4218P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2006
_refine_ls_wR_factor_ref         0.2306
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C27(H27), C32(H32), C46(H46), C61(H61), C70(H70), C71(H71),
 C77(H77), C91(H91), C93(H93)
2.c Idealised Me refined as rotating group:
 C84(H84A,H84B,H84C), C85(H85A,H85B,H85C), C88(H88A,H88B,H88C), C98(H98A,H98B,
 H98C)
2.d Idealised tetrahedral OH refined as rotating group:
 O19(H19)
;
_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
O5 O 0.5174(2) 0.2950(6) 0.46657(8) 0.0311(7) Uani 1 1 d . . . . .
O10 O 0.1414(2) 0.0152(5) 0.33843(8) 0.0292(7) Uani 1 1 d . . . . .
O12 O 0.0551(2) 0.6123(6) 0.18164(8) 0.0294(7) Uani 1 1 d . . . . .
O17 O -0.3097(2) 0.0953(6) 0.30940(9) 0.0328(8) Uani 1 1 d . . . . .
O19 O -0.4000(2) 0.4557(6) 0.34967(9) 0.0318(7) Uani 1 1 d . . . . .
H19 H -0.4269 0.3385 0.3365 0.048 Uiso 1 1 calc GR . . . .
O21 O -0.2875(2) 0.7807(5) 0.39375(9) 0.0294(7) Uani 1 1 d . . . . .
O27 O 0.0313(2) 0.0834(6) 0.41729(9) 0.0352(8) Uani 1 1 d . . . . .
C6 C -0.0691(3) 0.3874(8) 0.35991(11) 0.0213(9) Uani 1 1 d . . . . .
C9 C 0.2037(3) 0.2587(7) 0.41799(11) 0.0219(9) Uani 1 1 d . . . . .
C11 C 0.4152(3) 0.2947(8) 0.44977(11) 0.0235(9) Uani 1 1 d . . . . .
C15 C 0.0524(3) 0.3691(8) 0.36493(12) 0.0226(9) Uani 1 1 d . . . . .
H15 H 0.0818 0.5433 0.3661 0.027 Uiso 1 1 calc R . . . .
C17 C 0.1384(3) 0.2049(8) 0.26433(13) 0.0266(10) Uani 1 1 d . . . . .
H17 H 0.1773 0.0566 0.2704 0.032 Uiso 1 1 calc R . . . .
C20 C 0.0928(3) 0.3363(7) 0.29309(12) 0.0213(9) Uani 1 1 d . . . . .
C27 C 0.1276(3) 0.2884(8) 0.22665(12) 0.0255(9) Uani 1 1 d . . . . .
H27 H 0.1581 0.1963 0.2076 0.031 Uiso 1 1 calc R . . . .
C30 C 0.0996(3) 0.2258(8) 0.33214(12) 0.0232(9) Uani 1 1 d . . . . .
C32 C -0.1306(3) 0.2203(8) 0.33651(11) 0.0233(9) Uani 1 1 d . . . . .
H32 H -0.0976 0.0929 0.3232 0.028 Uiso 1 1 calc R . . . .
C41 C -0.2412(3) 0.2420(8) 0.33286(11) 0.0243(9) Uani 1 1 d . . . . .
C44 C 0.0703(3) 0.5127(8) 0.21768(11) 0.0232(9) Uani 1 1 d . . . . .
C46 C -0.1187(3) 0.5790(8) 0.37958(11) 0.0225(9) Uani 1 1 d . . . . .
H46 H -0.0780 0.6933 0.3951 0.027 Uiso 1 1 calc R . . . .
C52 C -0.2303(3) 0.5988(7) 0.37586(11) 0.0208(8) Uani 1 1 d . . . . .
C57 C 0.0913(3) 0.2271(8) 0.40235(12) 0.0224(9) Uani 1 1 d . . . . .
C61 C 0.3759(3) 0.4703(8) 0.42222(12) 0.0267(10) Uani 1 1 d . . . . .
H61 H 0.4198 0.5999 0.4143 0.032 Uiso 1 1 calc R . . . .
C63 C -0.2914(3) 0.4299(8) 0.35291(11) 0.0225(9) Uani 1 1 d . . . . .
C70 C 0.2449(3) 0.0842(8) 0.44582(12) 0.0267(9) Uani 1 1 d . . . . .
H70 H 0.2009 -0.0448 0.4539 0.032 Uiso 1 1 calc R . . . .
C71 C 0.0372(3) 0.5639(8) 0.28365(12) 0.0248(9) Uani 1 1 d . . . . .
H71 H 0.0078 0.6579 0.3027 0.030 Uiso 1 1 calc R . . . .
C77 C 0.0258(3) 0.6489(8) 0.24645(12) 0.0262(9) Uani 1 1 d . . . . .
H77 H -0.0121 0.7988 0.2405 0.031 Uiso 1 1 calc R . . . .
C84 C 0.5876(3) 0.4925(9) 0.45512(13) 0.0350(11) Uani 1 1 d . . . . .
H84A H 0.5953 0.4779 0.4282 0.053 Uiso 1 1 calc GR . . . .
H84B H 0.6563 0.4744 0.4691 0.053 Uiso 1 1 calc GR . . . .
H84C H 0.5582 0.6573 0.4604 0.053 Uiso 1 1 calc GR . . . .
C85 C -0.2660(3) -0.0946(8) 0.28587(12) 0.0289(10) Uani 1 1 d . . . . .
H85A H -0.3228 -0.1775 0.2704 0.043 Uiso 1 1 calc GR . . . .
H85B H -0.2277 -0.2195 0.3018 0.043 Uiso 1 1 calc GR . . . .
H85C H -0.2181 -0.0146 0.2696 0.043 Uiso 1 1 calc GR . . . .
C88 C -0.2313(3) 0.9405(8) 0.42201(13) 0.0305(10) Uani 1 1 d . . . . .
H88A H -0.1812 1.0461 0.4100 0.046 Uiso 1 1 calc GR . . . .
H88B H -0.1936 0.8351 0.4412 0.046 Uiso 1 1 calc GR . . . .
H88C H -0.2814 1.0474 0.4338 0.046 Uiso 1 1 calc GR . . . .
C91 C 0.3503(3) 0.0997(8) 0.46163(13) 0.0288(10) Uani 1 1 d . . . . .
H91 H 0.3768 -0.0188 0.4799 0.035 Uiso 1 1 calc R . . . .
C93 C 0.2709(3) 0.4514(8) 0.40667(12) 0.0281(10) Uani 1 1 d . . . . .
H93 H 0.2448 0.5698 0.3883 0.034 Uiso 1 1 calc R . . . .
C98 C 0.0828(4) 0.4571(9) 0.14967(13) 0.0370(11) Uani 1 1 d . . . . .
H98A H 0.0623 0.5450 0.1261 0.056 Uiso 1 1 calc GR . . . .
H98B H 0.0459 0.2960 0.1500 0.056 Uiso 1 1 calc GR . . . .
H98C H 0.1585 0.4273 0.1518 0.056 Uiso 1 1 calc GR . . . .


_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
O5 C11 1.365(4) . ?
O5 C84 1.435(5) . ?
O10 C30 1.229(4) . ?
O12 C44 1.363(5) . ?
O12 C98 1.448(5) . ?
O17 C41 1.371(5) . ?
O17 C85 1.428(5) . ?
O19 C63 1.366(4) . ?
O21 C52 1.373(5) . ?
O21 C88 1.433(5) . ?
O27 C57 1.213(5) . ?
C6 C15 1.524(5) . ?
C6 C32 1.385(5) . ?
C6 C46 1.392(6) . ?
C9 C57 1.478(5) . ?
C9 C70 1.400(5) . ?
C9 C93 1.392(5) . ?
C11 C61 1.390(6) . ?
C11 C91 1.389(6) . ?
C15 C30 1.531(6) . ?
C15 C57 1.547(5) . ?
C17 C20 1.382(6) . ?
C17 C27 1.385(6) . ?
C20 C30 1.480(6) . ?
C20 C71 1.403(5) . ?
C27 C44 1.396(5) . ?
C32 C41 1.388(5) . ?
C41 C63 1.388(6) . ?
C44 C77 1.389(6) . ?
C46 C52 1.400(5) . ?
C52 C63 1.380(5) . ?
C61 C93 1.386(5) . ?
C70 C91 1.393(5) . ?
C71 C77 1.372(6) . ?

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
C11 O5 C84 117.2(3) . . ?
C44 O12 C98 118.6(3) . . ?
C41 O17 C85 118.7(3) . . ?
C52 O21 C88 118.1(3) . . ?
C32 C6 C15 122.1(3) . . ?
C32 C6 C46 119.6(4) . . ?
C46 C6 C15 118.3(3) . . ?
C70 C9 C57 118.0(3) . . ?
C93 C9 C57 123.9(4) . . ?
C93 C9 C70 118.1(4) . . ?
O5 C11 C61 124.3(4) . . ?
O5 C11 C91 115.2(4) . . ?
C91 C11 C61 120.5(4) . . ?
C6 C15 C30 113.1(3) . . ?
C6 C15 C57 111.6(3) . . ?
C30 C15 C57 106.7(3) . . ?
C20 C17 C27 121.7(4) . . ?
C17 C20 C30 119.1(4) . . ?
C17 C20 C71 118.5(4) . . ?
C71 C20 C30 122.4(4) . . ?
C17 C27 C44 119.0(4) . . ?
O10 C30 C15 119.3(4) . . ?
O10 C30 C20 120.2(4) . . ?
C20 C30 C15 120.5(3) . . ?
C6 C32 C41 120.4(4) . . ?
O17 C41 C32 125.5(4) . . ?
O17 C41 C63 114.1(3) . . ?
C63 C41 C32 120.3(4) . . ?
O12 C44 C27 123.9(4) . . ?
O12 C44 C77 116.3(4) . . ?
C77 C44 C27 119.8(4) . . ?
C6 C46 C52 119.6(4) . . ?
O21 C52 C46 124.5(4) . . ?
O21 C52 C63 114.9(3) . . ?
C63 C52 C46 120.6(4) . . ?
O27 C57 C9 121.1(4) . . ?
O27 C57 C15 119.9(4) . . ?
C9 C57 C15 118.8(3) . . ?
C93 C61 C11 119.7(4) . . ?
O19 C63 C41 121.4(4) . . ?
O19 C63 C52 119.1(3) . . ?
C52 C63 C41 119.5(3) . . ?
C91 C70 C9 121.4(4) . . ?
C77 C71 C20 120.4(4) . . ?
C71 C77 C44 120.5(4) . . ?
C11 C91 C70 119.1(4) . . ?
C61 C93 C9 121.3(4) . . ?


_olex2_date_sample_data_collection 2019-06-15
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.370
_oxdiff_exptl_absorpt_empirical_full_min 0.507
####################################################################### 
# 
# 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_adjp393
_database_code_depnum_ccdc_archive 'CCDC 1944707'
loop_
_audit_author_name
_audit_author_address
'zhen he'
;School of chemistry university of manchester
United Kingdom
;
_audit_update_record             
;
2019-08-01 deposited with the CCDC.	2020-01-20 downloaded from the CCDC.
;
_audit_creation_date             2019-06-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C25 H28 O8'
_chemical_formula_sum            'C25 H28 O8'
_chemical_formula_weight         456.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   29.9022(18)
_cell_length_b                   11.0935(6)
_cell_length_c                   13.4816(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.730(5)
_cell_angle_gamma                90
_cell_volume                     4407.8(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4608
_cell_measurement_temperature    149.9(3)
_cell_measurement_theta_max      28.4220
_cell_measurement_theta_min      2.9930
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12291
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.150
_diffrn_reflns_theta_min         2.764
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00   3.00   1.00    9.49    --  -18.77 -57.00 -90.00   91
  2  ω    -20.00  25.00   1.00    9.49    --  -18.77 -99.00-180.00   45
  3  ω    -39.00  19.00   1.00    9.49    --  -18.77  57.00  60.00   58
  4  ω     -7.00  90.00   1.00    9.49    --   20.02  38.00-150.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0205143000
_diffrn_orient_matrix_UB_12      -0.0333884000
_diffrn_orient_matrix_UB_13      -0.0086318000
_diffrn_orient_matrix_UB_21      -0.0125531000
_diffrn_orient_matrix_UB_22      0.0541374000
_diffrn_orient_matrix_UB_23      0.0012469000
_diffrn_orient_matrix_UB_31      -0.0010397000
_diffrn_orient_matrix_UB_32      0.0068427000
_diffrn_orient_matrix_UB_33      -0.0526147000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3801
_reflns_number_total             5108
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5108
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0545
_refine_ls_restrained_S_all      1.042
_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)+(0.0434P)²+5.6515P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1334
_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, All O(H) groups
2. Others
 Fixed Sof: C1(0.5) C2(0.5) H2A(0.5) H1A(0.5) H2B(0.5) H1B(0.5) H1C(0.5)
 H2C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00K(H00K), C00L(H00L), C00M(H00M), C00O(H00O)
3.b Idealised Me refined as rotating group:
 C00R(H00A,H00D,H00E), C00S(H00F,H00G,H00H), C00T(H00I,H00J,H00N), C00U(H00P,
 H00Q,H00R), C00V(H00S,H00T,H00U), C00W(H00V,H00W,H00X)
3.c Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.32949(5) 0.54787(13) 0.34615(10) 0.0245(3) Uani 1 1 d . . . . .
H001 H 0.3104 0.5786 0.3752 0.037 Uiso 1 1 calc GR . . . .
O002 O 0.44569(5) 0.47396(13) 0.17708(10) 0.0264(3) Uani 1 1 d . . . . .
O003 O 0.20716(5) 0.96913(14) 0.46833(10) 0.0277(3) Uani 1 1 d . . . . .
O004 O 0.48436(5) 0.82955(14) 0.39261(11) 0.0331(4) Uani 1 1 d . . . . .
O005 O 0.27316(5) 0.93244(13) 0.61323(10) 0.0283(3) Uani 1 1 d . . . . .
O006 O 0.29151(5) 0.77648(15) 0.23251(10) 0.0344(4) Uani 1 1 d . . . . .
O007 O 0.42034(6) 0.06536(13) 0.28591(12) 0.0403(4) Uani 1 1 d . . . . .
O008 O 0.38237(6) 0.14726(14) 0.43136(12) 0.0430(4) Uani 1 1 d . . . . .
C009 C 0.40780(7) 0.56967(17) 0.33797(12) 0.0193(4) Uani 1 1 d . . . . .
C00A C 0.36707(7) 0.62072(18) 0.35633(13) 0.0198(4) Uani 1 1 d . . . . .
C00B C 0.44647(7) 0.64231(18) 0.34735(13) 0.0207(4) Uani 1 1 d . . . . .
H00B H 0.4733 0.6105 0.3324 0.025 Uiso 1 1 calc R . . . .
C00C C 0.31909(7) 0.83971(17) 0.49961(14) 0.0211(4) Uani 1 1 d . . . . .
H00C H 0.3436 0.8295 0.5513 0.025 Uiso 1 1 calc R . . . .
C00D C 0.32233(7) 0.79891(17) 0.40268(14) 0.0213(4) Uani 1 1 d . . . . .
C00E C 0.44536(7) 0.76124(18) 0.37863(14) 0.0223(4) Uani 1 1 d . . . . .
C00F C 0.36540(7) 0.74265(18) 0.38373(13) 0.0207(4) Uani 1 1 d . . . . .
C00G C 0.28031(7) 0.89460(18) 0.51979(13) 0.0219(4) Uani 1 1 d . . . . .
C00H C 0.41144(7) 0.43754(17) 0.31945(13) 0.0196(4) Uani 1 1 d . . . . .
C00I C 0.43106(6) 0.39218(18) 0.24085(13) 0.0204(4) Uani 1 1 d . . . . .
C00J C 0.24417(7) 0.91281(18) 0.44133(14) 0.0220(4) Uani 1 1 d . . . . .
C00K C 0.43475(7) 0.26732(19) 0.22772(14) 0.0251(4) Uani 1 1 d . . . . .
H00K H 0.4482 0.2376 0.1753 0.030 Uiso 1 1 calc R . . . .
C00L C 0.40491(7) 0.81119(18) 0.39627(14) 0.0234(4) Uani 1 1 d . . . . .
H00L H 0.4042 0.8912 0.4167 0.028 Uiso 1 1 calc R . . . .
C00M C 0.24665(7) 0.87484(18) 0.34444(14) 0.0236(4) Uani 1 1 d . . . . .
H00M H 0.2226 0.8883 0.2922 0.028 Uiso 1 1 calc R . . . .
C00N C 0.28581(7) 0.81597(18) 0.32611(14) 0.0231(4) Uani 1 1 d . . . . .
C00O C 0.39543(7) 0.35542(19) 0.38387(14) 0.0259(5) Uani 1 1 d . . . . .
H00O H 0.3823 0.3848 0.4368 0.031 Uiso 1 1 calc R . . . .
C00P C 0.41847(8) 0.18819(19) 0.29267(15) 0.0286(5) Uani 1 1 d . . . . .
C00Q C 0.39840(8) 0.23222(19) 0.37163(15) 0.0297(5) Uani 1 1 d . . . . .
C00R C 0.45797(7) 0.4280(2) 0.08638(14) 0.0297(5) Uani 1 1 d . . . . .
H00A H 0.4634 0.4939 0.0438 0.045 Uiso 1 1 calc GR . . . .
H00D H 0.4338 0.3790 0.0520 0.045 Uiso 1 1 calc GR . . . .
H00E H 0.4850 0.3803 0.1024 0.045 Uiso 1 1 calc GR . . . .
C00S C 0.31083(8) 0.9252(2) 0.69286(14) 0.0312(5) Uani 1 1 d . . . . .
H00F H 0.3349 0.9754 0.6776 0.047 Uiso 1 1 calc GR . . . .
H00G H 0.3211 0.8433 0.7005 0.047 Uiso 1 1 calc GR . . . .
H00H H 0.3019 0.9522 0.7543 0.047 Uiso 1 1 calc GR . . . .
C00T C 0.16793(7) 0.9804(2) 0.39309(16) 0.0365(6) Uani 1 1 d . . . . .
H00I H 0.1741 1.0350 0.3419 0.055 Uiso 1 1 calc GR . . . .
H00J H 0.1432 1.0108 0.4229 0.055 Uiso 1 1 calc GR . . . .
H00N H 0.1600 0.9028 0.3637 0.055 Uiso 1 1 calc GR . . . .
C00U C 0.25323(8) 0.7745(2) 0.15438(15) 0.0352(5) Uani 1 1 d . . . . .
H00P H 0.2609 0.7332 0.0970 0.053 Uiso 1 1 calc GR . . . .
H00Q H 0.2442 0.8557 0.1359 0.053 Uiso 1 1 calc GR . . . .
H00R H 0.2286 0.7334 0.1774 0.053 Uiso 1 1 calc GR . . . .
C00V C 0.43571(10) 0.0150(2) 0.20073(18) 0.0463(7) Uani 1 1 d . . . . .
H00S H 0.4166 0.0421 0.1404 0.069 Uiso 1 1 calc GR . . . .
H00T H 0.4346 -0.0713 0.2043 0.069 Uiso 1 1 calc GR . . . .
H00U H 0.4663 0.0403 0.2000 0.069 Uiso 1 1 calc GR . . . .
C00W C 0.35928(11) 0.1918(3) 0.5085(2) 0.0560(8) Uani 1 1 d . . . . .
H00V H 0.3358 0.2464 0.4796 0.084 Uiso 1 1 calc GR . . . .
H00W H 0.3804 0.2333 0.5584 0.084 Uiso 1 1 calc GR . . . .
H00X H 0.3461 0.1255 0.5393 0.084 Uiso 1 1 calc GR . . . .
C1 C 0.49304(18) 0.9161(5) 0.4714(4) 0.0309(10) Uani 0.5 1 d . . P A -2
C2 C 0.52388(16) 0.7772(5) 0.4054(4) 0.0309(10) Uani 0.5 1 d . . P A -1
H2A H 0.5451(16) 0.829(5) 0.430(3) 0.031(13) Uiso 0.5 1 d . . P B -1
H1A H 0.4819(15) 0.883(4) 0.529(3) 0.033(12) Uiso 0.5 1 d . . P C -2
H2B H 0.5232(17) 0.717(5) 0.456(4) 0.044(14) Uiso 0.5 1 d . . P D -1
H1B H 0.524(2) 0.930(5) 0.480(4) 0.048(15) Uiso 0.5 1 d . . P E -2
H1C H 0.4754(17) 0.982(5) 0.447(4) 0.044(15) Uiso 0.5 1 d . . P F -2
H2C H 0.5290(19) 0.749(5) 0.344(4) 0.059(17) Uiso 0.5 1 d . . P G -1


_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
O001 H001 0.8200 . ?
O001 C00A 1.372(2) . ?
O002 C00I 1.371(2) . ?
O002 C00R 1.429(2) . ?
O003 C00J 1.372(2) . ?
O003 C00T 1.421(2) . ?
O004 C00E 1.377(2) . ?
O004 C1 1.422(5) . ?
O004 C2 1.302(5) . ?
O005 C00G 1.378(2) . ?
O005 C00S 1.421(2) . ?
O006 C00N 1.373(2) . ?
O006 C00U 1.419(3) . ?
O007 C00P 1.367(2) . ?
O007 C00V 1.421(3) . ?
O008 C00Q 1.377(3) . ?
O008 C00W 1.430(3) . ?
C009 C00A 1.402(3) . ?
C009 C00B 1.398(3) . ?
C009 C00H 1.494(3) . ?
C00A C00F 1.405(3) . ?
C00B H00B 0.9300 . ?
C00B C00E 1.387(3) . ?
C00C H00C 0.9300 . ?
C00C C00D 1.402(2) . ?
C00C C00G 1.377(3) . ?
C00D C00F 1.492(3) . ?
C00D C00N 1.383(3) . ?
C00E C00L 1.387(3) . ?
C00F C00L 1.391(3) . ?
C00G C00J 1.393(3) . ?
C00H C00I 1.389(2) . ?
C00H C00O 1.398(3) . ?
C00I C00K 1.403(3) . ?
C00J C00M 1.386(3) . ?
C00K H00K 0.9300 . ?
C00K C00P 1.385(3) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00N 1.399(3) . ?
C00O H00O 0.9300 . ?
C00O C00Q 1.381(3) . ?
C00P C00Q 1.396(3) . ?
C00R H00A 0.9600 . ?
C00R H00D 0.9600 . ?
C00R H00E 0.9600 . ?
C00S H00F 0.9600 . ?
C00S H00G 0.9600 . ?
C00S H00H 0.9600 . ?
C00T H00I 0.9600 . ?
C00T H00J 0.9600 . ?
C00T H00N 0.9600 . ?
C00U H00P 0.9600 . ?
C00U H00Q 0.9600 . ?
C00U H00R 0.9600 . ?
C00V H00S 0.9600 . ?
C00V H00T 0.9600 . ?
C00V H00U 0.9600 . ?
C00W H00V 0.9600 . ?
C00W H00W 0.9600 . ?
C00W H00X 0.9600 . ?
C1 H1A 0.97(5) . ?
C1 H1B 0.94(6) . ?
C1 H1C 0.93(6) . ?
C2 H2A 0.88(5) . ?
C2 H2B 0.96(5) . ?
C2 H2C 0.92(6) . ?

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
C00A O001 H001 109.5 . . ?
C00I O002 C00R 117.12(16) . . ?
C00J O003 C00T 117.14(15) . . ?
C00E O004 C1 121.1(2) . . ?
C2 O004 C00E 120.1(3) . . ?
C00G O005 C00S 116.59(15) . . ?
C00N O006 C00U 118.50(16) . . ?
C00P O007 C00V 117.88(18) . . ?
C00Q O008 C00W 116.58(18) . . ?
C00A C009 C00H 121.04(18) . . ?
C00B C009 C00A 118.76(17) . . ?
C00B C009 C00H 119.88(17) . . ?
O001 C00A C009 117.74(17) . . ?
O001 C00A C00F 121.89(17) . . ?
C009 C00A C00F 120.37(18) . . ?
C009 C00B H00B 119.5 . . ?
C00E C00B C009 120.92(18) . . ?
C00E C00B H00B 119.5 . . ?
C00D C00C H00C 119.3 . . ?
C00G C00C H00C 119.3 . . ?
C00G C00C C00D 121.35(18) . . ?
C00C C00D C00F 119.50(18) . . ?
C00N C00D C00C 118.78(18) . . ?
C00N C00D C00F 121.67(16) . . ?
O004 C00E C00B 120.12(18) . . ?
O004 C00E C00L 119.98(18) . . ?
C00L C00E C00B 119.90(19) . . ?
C00A C00F C00D 121.19(18) . . ?
C00L C00F C00A 119.39(18) . . ?
C00L C00F C00D 119.39(17) . . ?
O005 C00G C00J 115.43(17) . . ?
C00C C00G O005 125.53(18) . . ?
C00C C00G C00J 119.02(17) . . ?
C00I C00H C009 122.34(17) . . ?
C00I C00H C00O 118.09(18) . . ?
C00O C00H C009 119.56(16) . . ?
O002 C00I C00H 117.33(17) . . ?
O002 C00I C00K 122.25(17) . . ?
C00H C00I C00K 120.41(18) . . ?
O003 C00J C00G 114.93(16) . . ?
O003 C00J C00M 124.21(18) . . ?
C00M C00J C00G 120.86(18) . . ?
C00I C00K H00K 119.9 . . ?
C00P C00K C00I 120.15(18) . . ?
C00P C00K H00K 119.9 . . ?
C00E C00L C00F 120.54(18) . . ?
C00E C00L H00L 119.7 . . ?
C00F C00L H00L 119.7 . . ?
C00J C00M H00M 120.4 . . ?
C00J C00M C00N 119.21(18) . . ?
C00N C00M H00M 120.4 . . ?
O006 C00N C00D 115.93(17) . . ?
O006 C00N C00M 123.28(18) . . ?
C00D C00N C00M 120.73(17) . . ?
C00H C00O H00O 118.8 . . ?
C00Q C00O C00H 122.33(18) . . ?
C00Q C00O H00O 118.8 . . ?
O007 C00P C00K 124.53(19) . . ?
O007 C00P C00Q 115.28(19) . . ?
C00K C00P C00Q 120.19(19) . . ?
O008 C00Q C00O 124.85(19) . . ?
O008 C00Q C00P 116.33(19) . . ?
C00O C00Q C00P 118.82(19) . . ?
O002 C00R H00A 109.5 . . ?
O002 C00R H00D 109.5 . . ?
O002 C00R H00E 109.5 . . ?
H00A C00R H00D 109.5 . . ?
H00A C00R H00E 109.5 . . ?
H00D C00R H00E 109.5 . . ?
O005 C00S H00F 109.5 . . ?
O005 C00S H00G 109.5 . . ?
O005 C00S H00H 109.5 . . ?
H00F C00S H00G 109.5 . . ?
H00F C00S H00H 109.5 . . ?
H00G C00S H00H 109.5 . . ?
O003 C00T H00I 109.5 . . ?
O003 C00T H00J 109.5 . . ?
O003 C00T H00N 109.5 . . ?
H00I C00T H00J 109.5 . . ?
H00I C00T H00N 109.5 . . ?
H00J C00T H00N 109.5 . . ?
O006 C00U H00P 109.5 . . ?
O006 C00U H00Q 109.5 . . ?
O006 C00U H00R 109.5 . . ?
H00P C00U H00Q 109.5 . . ?
H00P C00U H00R 109.5 . . ?
H00Q C00U H00R 109.5 . . ?
O007 C00V H00S 109.5 . . ?
O007 C00V H00T 109.5 . . ?
O007 C00V H00U 109.5 . . ?
H00S C00V H00T 109.5 . . ?
H00S C00V H00U 109.5 . . ?
H00T C00V H00U 109.5 . . ?
O008 C00W H00V 109.5 . . ?
O008 C00W H00W 109.5 . . ?
O008 C00W H00X 109.5 . . ?
H00V C00W H00W 109.5 . . ?
H00V C00W H00X 109.5 . . ?
H00W C00W H00X 109.5 . . ?
O004 C1 H1A 108(3) . . ?
O004 C1 H1B 105(3) . . ?
O004 C1 H1C 105(3) . . ?
H1A C1 H1B 116(4) . . ?
H1A C1 H1C 109(4) . . ?
H1B C1 H1C 114(5) . . ?
O004 C2 H2A 110(3) . . ?
O004 C2 H2B 106(3) . . ?
O004 C2 H2C 109(4) . . ?
H2A C2 H2B 107(4) . . ?
H2A C2 H2C 110(5) . . ?
H2B C2 H2C 115(5) . . ?

_olex2_date_sample_data_collection 2019-06-06
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.994
_oxdiff_exptl_absorpt_empirical_full_min 0.359
