# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_vhlphtmin
_database_code_depnum_ccdc_archive 'CCDC 1992513'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;Spectropole, Aix Marseille University
France
;
_audit_update_record             
;
2020-03-24 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;
_audit_creation_date             2018-09-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C19 H16 O3)'
_chemical_formula_sum            'C38 H32 O6'
_chemical_formula_weight         584.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c19 h17 o3'
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                   9.9277(8)
_cell_length_b                   10.5377(6)
_cell_length_c                   15.220(2)
_cell_angle_alpha                73.411(9)
_cell_angle_beta                 81.291(9)
_cell_angle_gamma                89.961(6)
_cell_volume                     1506.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2763
_cell_measurement_temperature    293
_cell_measurement_theta_max      24.9190
_cell_measurement_theta_min      3.2340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8268
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.536
_diffrn_reflns_theta_min         2.828
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -47.00  10.00   1.00   45.00    --  -15.36 -77.00 -60.00   57
  2  ω     38.00  81.00   1.00   45.00    --  -15.36 178.00-180.00   43
  3  ω    -23.00 101.00   1.00   45.00    --   15.99  38.00-180.00  124
  4  ω     35.00 113.00   1.00   45.00    --   15.99-178.00 120.00   78
  5  ω    -79.00  54.00   1.00   45.00    --   15.99 -77.00-120.00  133
  6  ω    -24.00  57.00   1.00   45.00    --   15.99  38.00 -60.00   81
  7  ω    -71.00  44.00   1.00   45.00    --   15.99 -57.00 120.00  115
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0699976000
_diffrn_orient_matrix_UB_12      0.0161211000
_diffrn_orient_matrix_UB_13      -0.0180971000
_diffrn_orient_matrix_UB_21      0.0160385000
_diffrn_orient_matrix_UB_22      -0.0200622000
_diffrn_orient_matrix_UB_23      0.0456863000
_diffrn_orient_matrix_UB_31      0.0088371000
_diffrn_orient_matrix_UB_32      -0.0654248000
_diffrn_orient_matrix_UB_33      -0.0031899000
_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                4731
_reflns_number_total             8268
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.66
_reflns_special_details          
;
 _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 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (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    ?
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         8268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1019
_refine_ls_R_factor_gt           0.0535
_refine_ls_restrained_S_all      0.990
_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)+(0.0716P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1398
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.6264(13)
 0.3736(13)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C36(H36A,H36B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15),
 C18(H18), C22(H22), C23(H23), C24(H24), C25(H25), C30(H30), C31(H31), C33(H33),
  C34(H34), C37(H37)
3.c X=CH2 refined with riding coordinates:
 C19(H19A,H19B), C38(H38A,H38B)
3.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C35(H35A,H35B,H35C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1364(2) 0.15390(17) 0.35124(12) 0.0433(5) Uani 1 1 d . . . . .
O2 O 0.2569(2) 0.0386(2) 0.45916(16) 0.0556(6) Uani 1 1 d . . . . .
O3 O 0.2131(3) 0.7516(2) 0.12199(14) 0.0696(7) Uani 1 1 d . . . . .
C1 C 0.1689(4) 0.0384(3) 0.41322(19) 0.0410(8) Uani 1 1 d . . . . .
C2 C 0.0787(3) -0.0672(3) 0.40805(19) 0.0396(7) Uani 1 1 d . . . . .
C3 C 0.0739(3) -0.2001(3) 0.4561(2) 0.0476(8) Uani 1 1 d . . . . .
H3 H 0.134054 -0.234040 0.497396 0.057 Uiso 1 1 calc R . . . .
C4 C -0.0242(4) -0.2808(3) 0.4403(2) 0.0532(9) Uani 1 1 d . . . . .
H4 H -0.031476 -0.370695 0.472042 0.064 Uiso 1 1 calc R . . . .
C5 C -0.1110(4) -0.2285(3) 0.3779(2) 0.0532(9) Uani 1 1 d . . . . .
H5 H -0.177459 -0.284141 0.369335 0.064 Uiso 1 1 calc R . . . .
C6 C -0.1026(4) -0.0968(3) 0.32776(19) 0.0483(8) Uani 1 1 d . . . . .
H6 H -0.159597 -0.064239 0.283984 0.058 Uiso 1 1 calc R . . . .
C7 C -0.0070(3) -0.0136(3) 0.34407(19) 0.0367(7) Uani 1 1 d . . . . .
C8 C 0.0306(3) 0.1285(3) 0.30500(19) 0.0393(7) Uani 1 1 d . . . . .
C9 C -0.0094(3) 0.2267(3) 0.23810(19) 0.0393(7) Uani 1 1 d . . . . .
C10 C 0.0495(3) 0.3643(3) 0.21126(18) 0.0383(7) Uani 1 1 d . . . . .
C11 C 0.0791(3) 0.4373(3) 0.11827(19) 0.0524(9) Uani 1 1 d . . . . .
H11 H 0.060789 0.398621 0.073308 0.063 Uiso 1 1 calc R . . . .
C12 C 0.1340(4) 0.5633(3) 0.0908(2) 0.0582(11) Uani 1 1 d . . . . .
H12 H 0.154777 0.608334 0.027926 0.070 Uiso 1 1 calc R . . . .
C13 C 0.1589(4) 0.6246(3) 0.1562(2) 0.0478(8) Uani 1 1 d . . . . .
C14 C 0.1287(3) 0.5569(3) 0.2486(2) 0.0470(8) Uani 1 1 d . . . . .
H14 H 0.143860 0.597495 0.293246 0.056 Uiso 1 1 calc R . . . .
C15 C 0.0759(3) 0.4283(3) 0.27505(19) 0.0452(8) Uani 1 1 d . . . . .
H15 H 0.057412 0.382840 0.337965 0.054 Uiso 1 1 calc R . . . .
C16 C 0.2382(4) 0.8202(3) 0.1855(2) 0.0706(11) Uani 1 1 d . . . . .
H16A H 0.283414 0.904417 0.152183 0.106 Uiso 1 1 calc GR . . . .
H16B H 0.294965 0.769068 0.227069 0.106 Uiso 1 1 calc GR . . . .
H16C H 0.153182 0.833667 0.220366 0.106 Uiso 1 1 calc GR . . . .
C17 C -0.1134(3) 0.1978(3) 0.1835(2) 0.0503(8) Uani 1 1 d . . . . .
H17A H -0.155993 0.279850 0.156842 0.060 Uiso 1 1 calc R . . . .
H17B H -0.183864 0.137651 0.226135 0.060 Uiso 1 1 calc R . . . .
C18 C -0.0610(4) 0.1387(3) 0.1065(2) 0.0568(9) Uani 1 1 d . . . . .
H18 H -0.124861 0.121368 0.072111 0.068 Uiso 1 1 calc R . . . .
C19 C 0.0634(5) 0.1093(4) 0.0830(3) 0.0740(13) Uani 1 1 d . . . . .
H19A H 0.131257 0.124615 0.115170 0.089 Uiso 1 1 calc R . . . .
H19B H 0.084768 0.072857 0.033996 0.089 Uiso 1 1 calc R . . . .
O4 O 0.4317(2) 0.65208(17) 0.35222(12) 0.0441(5) Uani 1 1 d . . . . .
O5 O 0.2607(2) 0.53658(19) 0.45914(16) 0.0577(6) Uani 1 1 d . . . . .
O6 O 0.4840(3) 1.2570(2) 0.12515(15) 0.0764(8) Uani 1 1 d . . . . .
C20 C 0.3707(4) 0.5375(3) 0.41346(19) 0.0409(8) Uani 1 1 d . . . . .
C21 C 0.4642(3) 0.4311(3) 0.40949(19) 0.0390(7) Uani 1 1 d . . . . .
C22 C 0.4463(3) 0.2977(3) 0.45801(19) 0.0489(8) Uani 1 1 d . . . . .
H22 H 0.366951 0.264266 0.499393 0.059 Uiso 1 1 calc R . . . .
C23 C 0.5509(4) 0.2161(3) 0.4426(2) 0.0558(9) Uani 1 1 d . . . . .
H23 H 0.543267 0.126168 0.474450 0.067 Uiso 1 1 calc R . . . .
C24 C 0.6673(4) 0.2688(3) 0.3794(2) 0.0534(9) Uani 1 1 d . . . . .
H24 H 0.737135 0.212849 0.370276 0.064 Uiso 1 1 calc R . . . .
C25 C 0.6832(4) 0.3999(3) 0.3301(2) 0.0490(8) Uani 1 1 d . . . . .
H25 H 0.761673 0.432277 0.287479 0.059 Uiso 1 1 calc R . . . .
C26 C 0.5784(3) 0.4848(3) 0.34520(19) 0.0401(8) Uani 1 1 d . . . . .
C27 C 0.5595(3) 0.6258(3) 0.30725(19) 0.0414(8) Uani 1 1 d . . . . .
C28 C 0.6314(3) 0.7250(3) 0.24018(19) 0.0424(8) Uani 1 1 d . . . . .
C29 C 0.5882(3) 0.8630(3) 0.21378(19) 0.0432(8) Uani 1 1 d . . . . .
C30 C 0.5272(3) 0.9250(3) 0.2774(2) 0.0484(9) Uani 1 1 d . . . . .
H30 H 0.510259 0.877158 0.339933 0.058 Uiso 1 1 calc R . . . .
C31 C 0.4904(3) 1.0557(3) 0.2514(2) 0.0485(8) Uani 1 1 d . . . . .
H31 H 0.450156 1.094704 0.295907 0.058 Uiso 1 1 calc R . . . .
C32 C 0.5139(4) 1.1273(3) 0.1593(2) 0.0525(9) Uani 1 1 d . . . . .
C33 C 0.5745(4) 1.0683(4) 0.0936(3) 0.0633(11) Uani 1 1 d . . . . .
H33 H 0.590074 1.116206 0.031128 0.076 Uiso 1 1 calc R . . . .
C34 C 0.6117(3) 0.9387(3) 0.1208(2) 0.0562(9) Uani 1 1 d . . . . .
H34 H 0.653467 0.900592 0.076202 0.067 Uiso 1 1 calc R . . . .
C35 C 0.4147(4) 1.3203(3) 0.1878(2) 0.0730(11) Uani 1 1 d . . . . .
H35A H 0.392730 1.407667 0.154214 0.110 Uiso 1 1 calc GR . . . .
H35B H 0.471884 1.326297 0.232064 0.110 Uiso 1 1 calc GR . . . .
H35C H 0.332177 1.269822 0.219686 0.110 Uiso 1 1 calc GR . . . .
C36 C 0.7628(3) 0.6936(3) 0.1864(2) 0.0558(9) Uani 1 1 d . . . . .
H36A H 0.818512 0.775001 0.159340 0.067 Uiso 1 1 calc R . . . .
H36B H 0.812404 0.633581 0.229941 0.067 Uiso 1 1 calc R . . . .
C37 C 0.7463(5) 0.6335(4) 0.1111(2) 0.0705(12) Uani 1 1 d . . . . .
H37 H 0.825574 0.608131 0.080656 0.085 Uiso 1 1 calc R . . . .
C38 C 0.6333(6) 0.6126(4) 0.0833(3) 0.0831(14) Uani 1 1 d . . . . .
H38A H 0.551068 0.636126 0.111419 0.100 Uiso 1 1 calc R . . . .
H38B H 0.634455 0.574134 0.035315 0.100 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.383(3) . ?
O1 C8 1.415(3) . ?
O2 C1 1.200(3) . ?
O3 C13 1.367(3) . ?
O3 C16 1.411(3) . ?
C1 C2 1.456(4) . ?
C2 C3 1.379(4) . ?
C2 C7 1.389(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.389(4) . ?
C7 C8 1.470(4) . ?
C8 C9 1.336(4) . ?
C9 C10 1.484(4) . ?
C9 C17 1.502(4) . ?
C10 C11 1.391(4) . ?
C10 C15 1.384(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.360(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(4) . ?
C13 C14 1.370(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(4) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.504(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.295(5) . ?
C19 H19A 0.9300 . ?
C19 H19B 0.9300 . ?
O4 C20 1.371(3) . ?
O4 C27 1.414(3) . ?
O5 C20 1.201(3) . ?
O6 C32 1.367(4) . ?
O6 C35 1.411(4) . ?
C20 C21 1.464(4) . ?
C21 C22 1.386(4) . ?
C21 C26 1.383(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.383(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.389(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.367(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.407(4) . ?
C26 C27 1.456(4) . ?
C27 C28 1.347(4) . ?
C28 C29 1.476(4) . ?
C28 C36 1.521(4) . ?
C29 C30 1.384(4) . ?
C29 C34 1.395(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.386(4) . ?
C31 H31 0.9300 . ?
C31 C32 1.373(4) . ?
C32 C33 1.386(4) . ?
C33 H33 0.9300 . ?
C33 C34 1.377(4) . ?
C34 H34 0.9300 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 C37 1.488(5) . ?
C37 H37 0.9300 . ?
C37 C38 1.298(6) . ?
C38 H38A 0.9300 . ?
C38 H38B 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
C1 O1 C8 110.6(2) . . ?
C13 O3 C16 118.5(3) . . ?
O1 C1 C2 107.0(3) . . ?
O2 C1 O1 121.0(3) . . ?
O2 C1 C2 132.0(3) . . ?
C3 C2 C1 128.3(3) . . ?
C3 C2 C7 123.0(3) . . ?
C7 C2 C1 108.7(3) . . ?
C2 C3 H3 121.4 . . ?
C2 C3 C4 117.2(3) . . ?
C4 C3 H3 121.4 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.0 . . ?
C6 C5 C4 122.1(3) . . ?
C6 C5 H5 119.0 . . ?
C5 C6 H6 120.8 . . ?
C5 C6 C7 118.4(3) . . ?
C7 C6 H6 120.8 . . ?
C2 C7 C8 107.6(3) . . ?
C6 C7 C2 118.8(3) . . ?
C6 C7 C8 133.6(3) . . ?
O1 C8 C7 106.1(2) . . ?
C9 C8 O1 119.5(3) . . ?
C9 C8 C7 134.4(3) . . ?
C8 C9 C10 122.9(3) . . ?
C8 C9 C17 119.7(3) . . ?
C10 C9 C17 117.4(3) . . ?
C11 C10 C9 120.5(3) . . ?
C15 C10 C9 123.3(3) . . ?
C15 C10 C11 116.2(3) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 C10 122.3(3) . . ?
C12 C11 H11 118.9 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.1(3) . . ?
C13 C12 H12 119.9 . . ?
O3 C13 C12 115.9(3) . . ?
O3 C13 C14 124.7(3) . . ?
C14 C13 C12 119.4(3) . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.7(3) . . ?
C15 C14 H14 120.2 . . ?
C10 C15 H15 118.9 . . ?
C14 C15 C10 122.3(3) . . ?
C14 C15 H15 118.9 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C9 C17 H17A 108.3 . . ?
C9 C17 H17B 108.3 . . ?
C9 C17 C18 116.1(3) . . ?
H17A C17 H17B 107.4 . . ?
C18 C17 H17A 108.3 . . ?
C18 C17 H17B 108.3 . . ?
C17 C18 H18 116.5 . . ?
C19 C18 C17 127.1(4) . . ?
C19 C18 H18 116.5 . . ?
C18 C19 H19A 120.0 . . ?
C18 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?
C20 O4 C27 110.2(2) . . ?
C32 O6 C35 117.9(3) . . ?
O4 C20 C21 107.2(3) . . ?
O5 C20 O4 121.5(3) . . ?
O5 C20 C21 131.2(3) . . ?
C22 C21 C20 128.4(3) . . ?
C26 C21 C20 108.2(3) . . ?
C26 C21 C22 123.4(3) . . ?
C21 C22 H22 121.2 . . ?
C23 C22 C21 117.5(3) . . ?
C23 C22 H22 121.2 . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C24 119.8(3) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 118.7 . . ?
C25 C24 C23 122.5(3) . . ?
C25 C24 H24 118.7 . . ?
C24 C25 H25 120.7 . . ?
C24 C25 C26 118.6(3) . . ?
C26 C25 H25 120.7 . . ?
C21 C26 C25 118.1(3) . . ?
C21 C26 C27 107.8(3) . . ?
C25 C26 C27 134.1(3) . . ?
O4 C27 C26 106.6(2) . . ?
C28 C27 O4 119.0(3) . . ?
C28 C27 C26 134.3(3) . . ?
C27 C28 C29 123.7(3) . . ?
C27 C28 C36 118.7(3) . . ?
C29 C28 C36 117.6(3) . . ?
C30 C29 C28 123.3(3) . . ?
C30 C29 C34 116.8(3) . . ?
C34 C29 C28 119.9(3) . . ?
C29 C30 H30 118.8 . . ?
C29 C30 C31 122.3(3) . . ?
C31 C30 H30 118.8 . . ?
C30 C31 H31 120.2 . . ?
C32 C31 C30 119.5(3) . . ?
C32 C31 H31 120.3 . . ?
O6 C32 C31 125.0(3) . . ?
O6 C32 C33 115.3(3) . . ?
C31 C32 C33 119.7(3) . . ?
C32 C33 H33 120.0 . . ?
C34 C33 C32 120.0(3) . . ?
C34 C33 H33 120.0 . . ?
C29 C34 H34 119.2 . . ?
C33 C34 C29 121.6(3) . . ?
C33 C34 H34 119.2 . . ?
O6 C35 H35A 109.5 . . ?
O6 C35 H35B 109.5 . . ?
O6 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C28 C36 H36A 108.3 . . ?
C28 C36 H36B 108.3 . . ?
H36A C36 H36B 107.4 . . ?
C37 C36 C28 115.8(3) . . ?
C37 C36 H36A 108.3 . . ?
C37 C36 H36B 108.3 . . ?
C36 C37 H37 116.5 . . ?
C38 C37 C36 127.0(4) . . ?
C38 C37 H37 116.5 . . ?
C37 C38 H38A 120.0 . . ?
C37 C38 H38B 120.0 . . ?
H38A C38 H38B 120.0 . . ?

_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 1.481
_oxdiff_exptl_absorpt_empirical_full_min 0.509
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.6264(13) 3847 13583 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.3736(13) 3813 13583 nmt 1.0001 -0.0011 -0.0010 -0.0005 -1.0006 0.0007
0.4604 -0.0027 -0.9995

_twin_special_details            
;
Component 2 rotated by -179.9064° 
 around [0.97 -0.00 0.22] (reciprocal) or [1.00 -0.00 -0.00] (direct)
;


####################################################################### 
# 
# 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_cyclo5ch
_database_code_depnum_ccdc_archive 'CCDC 1992514'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;Spectropole, Aix Marseille University
France
;
_audit_update_record             
;
2020-03-24 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;
_audit_creation_date             2016-04-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H20 O4'
_chemical_formula_sum            'C27 H20 O4'
_chemical_formula_weight         408.43
_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 0.0181 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/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                   13.5128(2)
_cell_length_b                   5.73808(8)
_cell_length_c                   26.7156(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.7159(16)
_cell_angle_gamma                90
_cell_volume                     2028.31(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13947
_cell_measurement_temperature    293
_cell_measurement_theta_max      65.1530
_cell_measurement_theta_min      5.4630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89149
_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    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_Laue_measured_fraction_full 0.946
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            24887
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         65.316
_diffrn_reflns_theta_min         4.039
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -110.00    8.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5201  -77.0000 -120.0000 118

#__ type_ start__ end____ width___ exp.time_
  2 omega  -27.00   53.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5201   38.0000  150.0000 80

#__ type_ start__ end____ width___ exp.time_
  3 omega  -49.00   54.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5201   38.0000    0.0000 103

#__ type_ start__ end____ width___ exp.time_
  4 omega -122.00    6.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5201  -57.0000   30.0000 128

#__ type_ start__ end____ width___ exp.time_
  5 omega   58.00  131.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       33.5201  178.0000  -60.0000 73

#__ type_ start__ end____ width___ exp.time_
  6 omega   35.00   82.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       33.5201  -99.0000  -30.0000 47

#__ type_ start__ end____ width___ exp.time_
  7 omega    5.00   30.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   90.0000  168.9528 25

#__ type_ start__ end____ width___ exp.time_
  8 omega    6.00   34.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   87.0000   39.4436 28

#__ type_ start__ end____ width___ exp.time_
  9 omega   11.00   36.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   84.0000  110.7460 25

#__ type_ start__ end____ width___ exp.time_
 10 omega   16.00   41.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   81.0000  -96.6131 25

#__ type_ start__ end____ width___ exp.time_
 11 omega   20.00   46.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   81.0000   74.9993 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   20.00   46.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   81.0000  121.7358 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   20.00   45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   81.0000   36.3694 25

#__ type_ start__ end____ width___ exp.time_
 14 omega   20.00   47.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   79.0000  -12.8973 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   20.00   46.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   81.0000  174.6470 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   20.00   45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   81.0000  -67.2709 25

#__ type_ start__ end____ width___ exp.time_
 17 omega   97.00  162.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000 -144.1121 65

#__ type_ start__ end____ width___ exp.time_
 18 omega   25.00   56.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000 -144.1121 31

#__ type_ start__ end____ width___ exp.time_
 19 omega   29.00   98.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000  -65.5087 69

#__ type_ start__ end____ width___ exp.time_
 20 omega   94.00  156.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   69.0000   41.5478 62

#__ type_ start__ end____ width___ exp.time_
 21 omega   34.00   61.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   69.0000   41.5478 27

#__ type_ start__ end____ width___ exp.time_
 22 omega  139.00  166.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   57.0000  153.8766 27

#__ type_ start__ end____ width___ exp.time_
 23 omega   39.00   85.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   57.0000  153.8766 46

#__ type_ start__ end____ width___ exp.time_
 24 omega   61.00  150.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  178.0000  120.0000 89

#__ type_ start__ end____ width___ exp.time_
 25 omega   56.00  130.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000 -180.0000 74

#__ type_ start__ end____ width___ exp.time_
 26 omega   37.00  107.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  -94.0000  120.0000 70

#__ type_ start__ end____ width___ exp.time_
 27 omega   56.00  144.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000  -30.0000 88

#__ type_ start__ end____ width___ exp.time_
 28 omega   56.00  162.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000   30.0000 106

#__ type_ start__ end____ width___ exp.time_
 29 omega   56.00  158.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000 -120.0000 102

#__ type_ start__ end____ width___ exp.time_
 30 omega   24.00  115.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141 -111.0000 -120.0000 91

#__ type_ start__ end____ width___ exp.time_
 31 omega   28.00  104.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141 -111.0000   90.0000 76

#__ type_ start__ end____ width___ exp.time_
 32 omega   56.00  163.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000   60.0000 107

#__ type_ start__ end____ width___ exp.time_
 33 omega   16.00  126.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  -61.0000 -150.0000 110

#__ type_ start__ end____ width___ exp.time_
 34 omega   56.00  172.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000 -150.0000 116

#__ type_ start__ end____ width___ exp.time_
 35 omega   56.00  135.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000    0.0000 79

#__ type_ start__ end____ width___ exp.time_
 36 omega   56.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000  -90.0000 122

#__ type_ start__ end____ width___ exp.time_
 37 omega   56.00  156.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000   90.0000 100

#__ type_ start__ end____ width___ exp.time_
 38 omega   56.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000  120.0000 122

#__ type_ start__ end____ width___ exp.time_
 39 omega   56.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000  -60.0000 122

#__ type_ start__ end____ width___ exp.time_
 40 omega   56.00  145.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   77.0000  150.0000 89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0898771000
_diffrn_orient_matrix_UB_12      -0.1706336000
_diffrn_orient_matrix_UB_13      0.0091967000
_diffrn_orient_matrix_UB_21      -0.0637361000
_diffrn_orient_matrix_UB_22      -0.1786624000
_diffrn_orient_matrix_UB_23      0.0227207000
_diffrn_orient_matrix_UB_31      -0.0376160000
_diffrn_orient_matrix_UB_32      -0.1051501000
_diffrn_orient_matrix_UB_33      -0.0535486000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3210
_reflns_number_total             3465
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     62.30
_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         0.126
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3465
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.049
_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)+(0.0494P)²+0.4332P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0969
_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:
 C1(H1), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C22(H22), C23(H23), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_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
O1 O 0.28625(9) -0.0427(2) 0.47651(5) 0.0825(4) Uani 1 1 d . . . . .
O2 O 0.09262(8) 0.75397(17) 0.37982(4) 0.0613(3) Uani 1 1 d . . . . .
O3 O 0.23306(10) -0.0636(2) 0.29642(5) 0.0812(4) Uani 1 1 d . . . . .
O4 O -0.35907(7) 0.33712(19) 0.31956(4) 0.0615(3) Uani 1 1 d . . . . .
C1 C 0.28231(9) 0.1539(2) 0.39940(5) 0.0469(3) Uani 1 1 d . . . . .
H1 H 0.3066 0.0008 0.3909 0.056 Uiso 1 1 calc R . . . .
C2 C 0.25341(10) 0.1267(3) 0.45123(6) 0.0546(4) Uani 1 1 d . . . . .
C3 C 0.19473(10) 0.3060(3) 0.47398(5) 0.0508(3) Uani 1 1 d . . . . .
C4 C 0.19663(12) 0.2750(3) 0.52635(6) 0.0694(5) Uani 1 1 d . . . . .
H4 H 0.2270 0.1420 0.5425 0.083 Uiso 1 1 calc R . . . .
C5 C 0.15522(15) 0.4345(4) 0.55452(7) 0.0825(6) Uani 1 1 d . . . . .
H5 H 0.1575 0.4082 0.5891 0.099 Uiso 1 1 calc R . . . .
C6 C 0.11059(15) 0.6323(4) 0.53167(7) 0.0788(6) Uani 1 1 d . . . . .
H6 H 0.0846 0.7434 0.5508 0.095 Uiso 1 1 calc R . . . .
C7 C 0.10438(12) 0.6653(3) 0.47991(6) 0.0608(4) Uani 1 1 d . . . . .
H7 H 0.0725 0.7981 0.4644 0.073 Uiso 1 1 calc R . . . .
C8 C 0.14456(9) 0.5049(2) 0.45017(5) 0.0465(3) Uani 1 1 d . . . . .
C9 C 0.12167(9) 0.5594(2) 0.39427(5) 0.0433(3) Uani 1 1 d . . . . .
C10 C 0.12662(9) 0.3809(2) 0.35488(5) 0.0399(3) Uani 1 1 d . . . . .
C11 C 0.05291(9) 0.3942(2) 0.30374(5) 0.0447(3) Uani 1 1 d . . . . .
H11 H 0.0621 0.5438 0.2876 0.054 Uiso 1 1 calc R . . . .
C12 C 0.08967(11) 0.1975(3) 0.27275(5) 0.0589(4) Uani 1 1 d . . . . .
H12A H 0.0371 0.0816 0.2629 0.071 Uiso 1 1 calc R . . . .
H12B H 0.1078 0.2596 0.2421 0.071 Uiso 1 1 calc R . . . .
C13 C 0.18054(11) 0.0915(3) 0.30713(5) 0.0528(3) Uani 1 1 d . . . . .
C14 C 0.19626(9) 0.2146(2) 0.35694(5) 0.0433(3) Uani 1 1 d . . . . .
C15 C 0.37292(9) 0.3198(2) 0.40465(5) 0.0420(3) Uani 1 1 d . . . . .
C16 C 0.45997(10) 0.2684(3) 0.44043(5) 0.0524(3) Uani 1 1 d . . . . .
H16 H 0.4621 0.1351 0.4604 0.063 Uiso 1 1 calc R . . . .
C17 C 0.54326(11) 0.4121(3) 0.44673(6) 0.0616(4) Uani 1 1 d . . . . .
H17 H 0.6009 0.3763 0.4710 0.074 Uiso 1 1 calc R . . . .
C18 C 0.54102(11) 0.6088(3) 0.41704(6) 0.0638(4) Uani 1 1 d . . . . .
H18 H 0.5969 0.7068 0.4213 0.077 Uiso 1 1 calc R . . . .
C19 C 0.45577(11) 0.6596(3) 0.38106(7) 0.0619(4) Uani 1 1 d . . . . .
H19 H 0.4544 0.7916 0.3607 0.074 Uiso 1 1 calc R . . . .
C20 C 0.37215(10) 0.5166(2) 0.37479(6) 0.0521(3) Uani 1 1 d . . . . .
H20 H 0.3149 0.5529 0.3503 0.063 Uiso 1 1 calc R . . . .
C21 C -0.05597(9) 0.3753(2) 0.30961(4) 0.0392(3) Uani 1 1 d . . . . .
C22 C -0.09066(10) 0.1810(2) 0.33169(5) 0.0452(3) Uani 1 1 d . . . . .
H22 H -0.0458 0.0612 0.3437 0.054 Uiso 1 1 calc R . . . .
C23 C -0.19077(10) 0.1611(2) 0.33625(5) 0.0474(3) Uani 1 1 d . . . . .
H23 H -0.2125 0.0294 0.3512 0.057 Uiso 1 1 calc R . . . .
C24 C -0.25816(9) 0.3384(2) 0.31836(5) 0.0435(3) Uani 1 1 d . . . . .
C25 C -0.22463(9) 0.5346(2) 0.29681(5) 0.0440(3) Uani 1 1 d . . . . .
H25 H -0.2695 0.6548 0.2850 0.053 Uiso 1 1 calc R . . . .
C26 C -0.12484(9) 0.5524(2) 0.29278(4) 0.0422(3) Uani 1 1 d . . . . .
H26 H -0.1031 0.6859 0.2785 0.051 Uiso 1 1 calc R . . . .
C27 C -0.39879(15) 0.1368(3) 0.33945(8) 0.0807(5) Uani 1 1 d . . . . .
H27A H -0.3641 0.1121 0.3741 0.121 Uiso 1 1 calc GR . . . .
H27B H -0.3896 0.0034 0.3192 0.121 Uiso 1 1 calc GR . . . .
H27C H -0.4695 0.1591 0.3385 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
O1 C2 1.2147(17) . ?
O2 C9 1.2198(16) . ?
O3 C13 1.2083(18) . ?
O4 C24 1.3705(16) . ?
O4 C27 1.417(2) . ?
C1 H1 0.9800 . ?
C1 C2 1.521(2) . ?
C1 C14 1.4914(17) . ?
C1 C15 1.5346(17) . ?
C2 C3 1.501(2) . ?
C3 C4 1.406(2) . ?
C3 C8 1.412(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.369(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.396(2) . ?
C8 C9 1.4955(18) . ?
C9 C10 1.4799(18) . ?
C10 C11 1.5204(16) . ?
C10 C14 1.3335(18) . ?
C11 H11 0.9800 . ?
C11 C12 1.540(2) . ?
C11 C21 1.5148(17) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.505(2) . ?
C13 C14 1.483(2) . ?
C15 C16 1.3883(18) . ?
C15 C20 1.3817(18) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.376(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.373(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.3788(19) . ?
C20 H20 0.9300 . ?
C21 C22 1.3865(17) . ?
C21 C26 1.3897(17) . ?
C22 H22 0.9300 . ?
C22 C23 1.3874(19) . ?
C23 H23 0.9300 . ?
C23 C24 1.3841(19) . ?
C24 C25 1.3820(18) . ?
C25 H25 0.9300 . ?
C25 C26 1.3780(18) . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
C24 O4 C27 117.88(12) . . ?
C2 C1 H1 106.2 . . ?
C2 C1 C15 109.14(11) . . ?
C14 C1 H1 106.2 . . ?
C14 C1 C2 114.31(11) . . ?
C14 C1 C15 114.14(10) . . ?
C15 C1 H1 106.2 . . ?
O1 C2 C1 117.12(15) . . ?
O1 C2 C3 119.12(14) . . ?
C3 C2 C1 123.55(11) . . ?
C4 C3 C2 114.33(14) . . ?
C4 C3 C8 117.44(15) . . ?
C8 C3 C2 128.10(12) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 C3 122.26(18) . . ?
C5 C4 H4 118.9 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 119.97(16) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 120.3 . . ?
C5 C6 C7 119.46(19) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 119.1 . . ?
C6 C7 C8 121.86(17) . . ?
C8 C7 H7 119.1 . . ?
C3 C8 C9 127.01(13) . . ?
C7 C8 C3 118.92(13) . . ?
C7 C8 C9 113.91(13) . . ?
O2 C9 C8 119.70(12) . . ?
O2 C9 C10 117.82(12) . . ?
C10 C9 C8 122.37(11) . . ?
C9 C10 C11 119.22(11) . . ?
C14 C10 C9 126.84(11) . . ?
C14 C10 C11 113.65(11) . . ?
C10 C11 H11 108.7 . . ?
C10 C11 C12 102.85(10) . . ?
C12 C11 H11 108.7 . . ?
C21 C11 C10 112.10(10) . . ?
C21 C11 H11 108.7 . . ?
C21 C11 C12 115.42(11) . . ?
C11 C12 H12A 110.5 . . ?
C11 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C13 C12 C11 106.29(11) . . ?
C13 C12 H12A 110.5 . . ?
C13 C12 H12B 110.5 . . ?
O3 C13 C12 126.81(14) . . ?
O3 C13 C14 125.39(14) . . ?
C14 C13 C12 107.79(12) . . ?
C10 C14 C1 129.29(12) . . ?
C10 C14 C13 109.41(11) . . ?
C13 C14 C1 121.24(12) . . ?
C16 C15 C1 118.68(12) . . ?
C20 C15 C1 122.82(11) . . ?
C20 C15 C16 118.49(12) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 120.93(14) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 119.91(14) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.63(14) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.61(14) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 H20 119.8 . . ?
C19 C20 C15 120.42(13) . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C11 121.39(11) . . ?
C22 C21 C26 117.62(11) . . ?
C26 C21 C11 120.99(11) . . ?
C21 C22 H22 119.2 . . ?
C21 C22 C23 121.56(12) . . ?
C23 C22 H22 119.2 . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.61(12) . . ?
C24 C23 H23 120.2 . . ?
O4 C24 C23 125.16(12) . . ?
O4 C24 C25 115.22(12) . . ?
C25 C24 C23 119.62(12) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.10(12) . . ?
C26 C25 H25 119.9 . . ?
C21 C26 H26 119.3 . . ?
C25 C26 C21 121.48(11) . . ?
C25 C26 H26 119.3 . . ?
O4 C27 H27A 109.5 . . ?
O4 C27 H27B 109.5 . . ?
O4 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

_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_photo5och3
_database_code_depnum_ccdc_archive 'CCDC 1992517'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;Spectropole, Aix Marseille University
France
;
_audit_update_record             
;
2020-03-24 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;
_audit_creation_date             2016-04-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H22 O4'
_chemical_formula_sum            'C28 H22 O4'
_chemical_formula_weight         422.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c27 h22 o4'
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                   20.9397(10)
_cell_length_b                   5.4322(2)
_cell_length_c                   19.3737(11)
_cell_angle_alpha                90
_cell_angle_beta                 99.981(5)
_cell_angle_gamma                90
_cell_volume                     2170.38(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5081
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.3940
_cell_measurement_theta_min      3.8430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73673
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14561
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.138
_diffrn_reflns_theta_min         3.879
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    1.00   32.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.0572 -121.0000   -9.0000 31

#__ type_ start__ end____ width___ exp.time_
  2 omega -104.00  -58.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.0572 -178.0000   90.0000 46

#__ type_ start__ end____ width___ exp.time_
  3 omega   46.00  103.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       11.8385  178.0000   30.0000 57

#__ type_ start__ end____ width___ exp.time_
  4 omega  -80.00  103.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       11.8385    0.0000   60.0000 183
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0290659000
_diffrn_orient_matrix_UB_12      0.0321213000
_diffrn_orient_matrix_UB_13      -0.0228130000
_diffrn_orient_matrix_UB_21      -0.0179541000
_diffrn_orient_matrix_UB_22      -0.0247683000
_diffrn_orient_matrix_UB_23      0.0270761000
_diffrn_orient_matrix_UB_31      0.0039352000
_diffrn_orient_matrix_UB_32      0.1241513000
_diffrn_orient_matrix_UB_33      0.0113090000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3200
_reflns_number_total             4561
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.66
_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         0.151
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4561
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.063
_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)+(0.0341P)²+0.7893P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1147
_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:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C17(H17), C18(H18), C20(H20), C21(H21),
 C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), 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
O1 O 0.23220(7) 0.8185(3) 0.58936(7) 0.0623(4) Uani 1 1 d . . . . .
O2 O 0.20178(7) -0.0482(2) 0.41331(8) 0.0600(4) Uani 1 1 d . . . . .
O3 O 0.40066(6) 0.6129(3) 0.43691(7) 0.0646(4) Uani 1 1 d . . . . .
O4 O -0.07827(6) 0.3352(3) 0.28665(7) 0.0621(4) Uani 1 1 d . . . . .
C1 C 0.31597(8) 0.5633(3) 0.49945(9) 0.0393(4) Uani 1 1 d . . . . .
C2 C 0.33775(8) 0.5390(3) 0.43842(9) 0.0448(4) Uani 1 1 d . . . . .
C3 C 0.30203(8) 0.4547(3) 0.37017(9) 0.0432(4) Uani 1 1 d . . . . .
C4 C 0.32148(9) 0.5512(4) 0.30993(10) 0.0557(5) Uani 1 1 d . . . . .
H4 H 0.3526 0.6751 0.3149 0.067 Uiso 1 1 calc R . . . .
C5 C 0.29610(10) 0.4690(5) 0.24394(11) 0.0645(6) Uani 1 1 d . . . . .
H5 H 0.3092 0.5394 0.2049 0.077 Uiso 1 1 calc R . . . .
C6 C 0.25134(11) 0.2826(5) 0.23583(11) 0.0686(6) Uani 1 1 d . . . . .
H6 H 0.2350 0.2226 0.1913 0.082 Uiso 1 1 calc R . . . .
C7 C 0.23064(10) 0.1844(4) 0.29342(11) 0.0581(5) Uani 1 1 d . . . . .
H7 H 0.2002 0.0583 0.2872 0.070 Uiso 1 1 calc R . . . .
C8 C 0.25425(8) 0.2693(3) 0.36097(9) 0.0421(4) Uani 1 1 d . . . . .
C9 C 0.22334(8) 0.1619(3) 0.41722(9) 0.0424(4) Uani 1 1 d . . . . .
C10 C 0.20986(8) 0.3278(3) 0.47316(9) 0.0388(4) Uani 1 1 d . . . . .
C11 C 0.14579(8) 0.3041(3) 0.49906(9) 0.0444(4) Uani 1 1 d . . . . .
H11 H 0.1461 0.1485 0.5247 0.053 Uiso 1 1 calc R . . . .
C12 C 0.14859(9) 0.5158(4) 0.55178(10) 0.0549(5) Uani 1 1 d . . . . .
H12A H 0.1140 0.6328 0.5365 0.066 Uiso 1 1 calc R . . . .
H12B H 0.1438 0.4532 0.5975 0.066 Uiso 1 1 calc R . . . .
C13 C 0.21367(8) 0.6375(4) 0.55544(9) 0.0450(4) Uani 1 1 d . . . . .
C14 C 0.24919(8) 0.5026(3) 0.50621(8) 0.0376(4) Uani 1 1 d . . . . .
C15 C 0.44296(10) 0.4201(6) 0.42188(15) 0.0905(8) Uani 1 1 d . . . . .
H15A H 0.4244 0.3405 0.3788 0.136 Uiso 1 1 calc GR . . . .
H15B H 0.4486 0.3020 0.4593 0.136 Uiso 1 1 calc GR . . . .
H15C H 0.4843 0.4887 0.4174 0.136 Uiso 1 1 calc GR . . . .
C16 C 0.08669(8) 0.3062(3) 0.44143(9) 0.0403(4) Uani 1 1 d . . . . .
C17 C 0.07508(9) 0.4975(3) 0.39325(10) 0.0493(5) Uani 1 1 d . . . . .
H17 H 0.1049 0.6251 0.3953 0.059 Uiso 1 1 calc R . . . .
C18 C 0.02030(9) 0.5013(3) 0.34269(10) 0.0504(5) Uani 1 1 d . . . . .
H18 H 0.0135 0.6312 0.3110 0.060 Uiso 1 1 calc R . . . .
C19 C -0.02490(8) 0.3137(3) 0.33854(10) 0.0454(4) Uani 1 1 d . . . . .
C20 C -0.01416(9) 0.1218(4) 0.38539(11) 0.0526(5) Uani 1 1 d . . . . .
H20 H -0.0440 -0.0061 0.3832 0.063 Uiso 1 1 calc R . . . .
C21 C 0.04161(8) 0.1205(3) 0.43597(10) 0.0489(5) Uani 1 1 d . . . . .
H21 H 0.0487 -0.0106 0.4672 0.059 Uiso 1 1 calc R . . . .
C22 C -0.12306(10) 0.1354(4) 0.27819(13) 0.0695(6) Uani 1 1 d . . . . .
H22A H -0.1549 0.1612 0.2368 0.104 Uiso 1 1 calc GR . . . .
H22B H -0.1441 0.1260 0.3183 0.104 Uiso 1 1 calc GR . . . .
H22C H -0.1003 -0.0155 0.2737 0.104 Uiso 1 1 calc GR . . . .
C23 C 0.35982(8) 0.6404(3) 0.56523(9) 0.0423(4) Uani 1 1 d . . . . .
C24 C 0.36371(9) 0.4940(4) 0.62417(10) 0.0492(5) Uani 1 1 d . . . . .
H24 H 0.3387 0.3518 0.6221 0.059 Uiso 1 1 calc R . . . .
C25 C 0.40406(10) 0.5547(4) 0.68623(11) 0.0635(6) Uani 1 1 d . . . . .
H25 H 0.4061 0.4530 0.7252 0.076 Uiso 1 1 calc R . . . .
C26 C 0.44079(10) 0.7625(5) 0.69043(13) 0.0687(6) Uani 1 1 d . . . . .
H26 H 0.4680 0.8028 0.7321 0.082 Uiso 1 1 calc R . . . .
C27 C 0.43743(10) 0.9119(4) 0.63303(14) 0.0703(6) Uani 1 1 d . . . . .
H27 H 0.4623 1.0545 0.6360 0.084 Uiso 1 1 calc R . . . .
C28 C 0.39708(10) 0.8524(4) 0.57027(12) 0.0586(5) Uani 1 1 d . . . . .
H28 H 0.3952 0.9554 0.5316 0.070 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.209(2) . ?
O2 C9 1.225(2) . ?
O3 C2 1.382(2) . ?
O3 C15 1.434(3) . ?
O4 C19 1.372(2) . ?
O4 C22 1.425(2) . ?
C1 C2 1.346(2) . ?
C1 C14 1.464(2) . ?
C1 C23 1.496(2) . ?
C2 C3 1.475(2) . ?
C3 C4 1.403(3) . ?
C3 C8 1.409(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.370(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.373(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.395(3) . ?
C8 C9 1.480(2) . ?
C9 C10 1.474(2) . ?
C10 C11 1.517(2) . ?
C10 C14 1.344(2) . ?
C11 H11 0.9800 . ?
C11 C12 1.532(3) . ?
C11 C16 1.516(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.505(3) . ?
C13 C14 1.499(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.389(2) . ?
C16 C21 1.373(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.373(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.384(3) . ?
C19 C20 1.375(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.388(3) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.382(3) . ?
C23 C28 1.385(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.384(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.361(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.368(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.393(3) . ?
C28 H28 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
C2 O3 C15 114.64(17) . . ?
C19 O4 C22 117.10(16) . . ?
C2 C1 C14 122.05(16) . . ?
C2 C1 C23 121.65(15) . . ?
C14 C1 C23 116.21(14) . . ?
O3 C2 C3 114.11(15) . . ?
C1 C2 O3 117.35(16) . . ?
C1 C2 C3 128.45(16) . . ?
C4 C3 C2 117.03(16) . . ?
C4 C3 C8 117.66(17) . . ?
C8 C3 C2 125.05(16) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 C3 122.16(19) . . ?
C5 C4 H4 118.9 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.6(2) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0(2) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C8 121.6(2) . . ?
C8 C7 H7 119.2 . . ?
C3 C8 C9 125.44(16) . . ?
C7 C8 C3 118.91(17) . . ?
C7 C8 C9 115.56(16) . . ?
O2 C9 C8 121.67(16) . . ?
O2 C9 C10 119.98(16) . . ?
C10 C9 C8 117.67(15) . . ?
C9 C10 C11 118.96(15) . . ?
C14 C10 C9 127.05(15) . . ?
C14 C10 C11 113.98(15) . . ?
C10 C11 H11 108.2 . . ?
C10 C11 C12 102.87(14) . . ?
C12 C11 H11 108.2 . . ?
C16 C11 C10 114.29(14) . . ?
C16 C11 H11 108.2 . . ?
C16 C11 C12 114.65(15) . . ?
C11 C12 H12A 110.3 . . ?
C11 C12 H12B 110.3 . . ?
H12A C12 H12B 108.6 . . ?
C13 C12 C11 106.90(14) . . ?
C13 C12 H12A 110.3 . . ?
C13 C12 H12B 110.3 . . ?
O1 C13 C12 125.84(17) . . ?
O1 C13 C14 126.58(17) . . ?
C14 C13 C12 107.49(16) . . ?
C1 C14 C13 122.26(16) . . ?
C10 C14 C1 129.22(15) . . ?
C10 C14 C13 108.53(15) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C11 121.73(16) . . ?
C21 C16 C11 120.89(16) . . ?
C21 C16 C17 117.37(17) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.19(17) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.56(17) . . ?
C19 C18 H18 119.7 . . ?
O4 C19 C18 116.23(17) . . ?
O4 C19 C20 124.55(17) . . ?
C20 C19 C18 119.22(17) . . ?
C19 C20 H20 120.3 . . ?
C19 C20 C21 119.41(17) . . ?
C21 C20 H20 120.3 . . ?
C16 C21 C20 122.25(17) . . ?
C16 C21 H21 118.9 . . ?
C20 C21 H21 118.9 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C1 118.84(16) . . ?
C24 C23 C28 117.93(18) . . ?
C28 C23 C1 123.23(17) . . ?
C23 C24 H24 119.3 . . ?
C23 C24 C25 121.35(19) . . ?
C25 C24 H24 119.3 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.2(2) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 120.2 . . ?
C25 C26 C27 119.6(2) . . ?
C27 C26 H26 120.2 . . ?
C26 C27 H27 119.7 . . ?
C26 C27 C28 120.6(2) . . ?
C28 C27 H27 119.7 . . ?
C23 C28 C27 120.2(2) . . ?
C23 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?

_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_photo5cch3
_database_code_depnum_ccdc_archive 'CCDC 1992515'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;Spectropole, Aix Marseille University
France
;
_audit_update_record             
;
2020-03-24 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;
_audit_creation_date             2016-04-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C28 H22 O4)'
_chemical_formula_sum            'C56 H44 O8'
_chemical_formula_weight         844.91
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c28 h22 o4'
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                   20.7429(9)
_cell_length_b                   19.0061(5)
_cell_length_c                   11.4935(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.220(3)
_cell_angle_gamma                90
_cell_volume                     4504.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4458
_cell_measurement_temperature    293
_cell_measurement_theta_max      63.4650
_cell_measurement_theta_min      4.4900
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73770
_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    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.940
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            26870
_diffrn_reflns_point_group_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         65.286
_diffrn_reflns_theta_min         4.288
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -133.00  -69.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5201 -166.0000 -124.0000 64

#__ type_ start__ end____ width___ exp.time_
  2 omega -115.00  -80.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5201  -99.0000 -180.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega  -41.00   46.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5201   38.0000 -180.0000 87

#__ type_ start__ end____ width___ exp.time_
  4 omega -120.00    8.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5201  -38.0000   30.0000 128

#__ type_ start__ end____ width___ exp.time_
  5 omega -119.00  -80.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5201  -99.0000  120.0000 39

#__ type_ start__ end____ width___ exp.time_
  6 omega   -4.00   24.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       33.5201   57.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
  7 omega   76.00  102.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       33.5201   57.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega    2.00   47.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       33.5201  -99.0000  -60.0000 45

#__ type_ start__ end____ width___ exp.time_
  9 omega   58.00  129.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       33.5201  178.0000  -60.0000 71

#__ type_ start__ end____ width___ exp.time_
 10 omega   16.00   55.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  -61.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
 11 omega   24.00   52.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  -30.0000   60.0000 28

#__ type_ start__ end____ width___ exp.time_
 12 omega   55.00  109.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  -94.0000  -30.0000 54

#__ type_ start__ end____ width___ exp.time_
 13 omega  146.00  173.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  111.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 14 omega   50.00  112.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141 -111.0000  120.0000 62

#__ type_ start__ end____ width___ exp.time_
 15 omega   71.00  121.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  178.0000    0.0000 50

#__ type_ start__ end____ width___ exp.time_
 16 omega   17.00   42.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141 -111.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 17 omega   11.00   89.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  -30.0000   90.0000 78

#__ type_ start__ end____ width___ exp.time_
 18 omega   20.00   62.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  -30.0000   30.0000 42

#__ type_ start__ end____ width___ exp.time_
 19 omega   59.00  115.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141 -111.0000 -120.0000 56

#__ type_ start__ end____ width___ exp.time_
 20 omega  102.00  130.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  111.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
 21 omega   69.00  137.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  -61.0000 -150.0000 68

#__ type_ start__ end____ width___ exp.time_
 22 omega  145.00  174.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  111.0000  120.0000 29

#__ type_ start__ end____ width___ exp.time_
 23 omega   21.00   91.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  -45.0000  -30.0000 70

#__ type_ start__ end____ width___ exp.time_
 24 omega   28.00  124.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  -61.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 25 omega    4.00   36.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141  -94.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega    3.00  178.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       97.5141   15.0000   60.0000 175
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0307613000
_diffrn_orient_matrix_UB_12      0.0705010000
_diffrn_orient_matrix_UB_13      -0.0424324000
_diffrn_orient_matrix_UB_21      -0.0671793000
_diffrn_orient_matrix_UB_22      -0.0274967000
_diffrn_orient_matrix_UB_23      0.0240223000
_diffrn_orient_matrix_UB_31      0.0111303000
_diffrn_orient_matrix_UB_32      0.0290567000
_diffrn_orient_matrix_UB_33      0.1256745000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4941
_reflns_number_total             7659
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     62.30
_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         0.587
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     571
_refine_ls_number_reflns         7659
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0653
_refine_ls_restrained_S_all      1.033
_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)+(0.0798P)²+2.1018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1615
_refine_ls_wR_factor_ref         0.1877
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O7-C61
 1.45 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C53 \\sim O7 \\sim C61: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02
C58 \\sim O8 \\sim C62: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C50) = Uanis(C51) = Uanis(C52) = Uanis(C53) = Uanis(C54) = Uanis(C55) =
Uanis(C56) = Uanis(C57) = Uanis(C58) = Uanis(C59) = Uanis(C60)
4. Others
 Fixed Sof: O7(0.5) O8(0.5) C51(0.5) H51(0.5) C52(0.5) H52(0.5) C53(0.5)
 C54(0.5) H54(0.5) C55(0.5) H55(0.5) C56(0.5) H56(0.5) C57(0.5) H57(0.5)
 C58(0.5) C59(0.5) H59(0.5) C60(0.5) H60(0.5) C61(0.5) H61A(0.5) H61B(0.5)
 H61C(0.5) C62(0.5) H62A(0.5) H62B(0.5) H62C(0.5)
5.a Ternary CH refined with riding coordinates:
 C33(H33), C5AA(H5AA)
5.b Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B), C1AA(H1AA,H1AB)
5.c Aromatic/amide H refined with riding coordinates:
 C37(H37), C38(H38), C39(H39), C40(H40), C44(H44), C45(H45), C46(H46),
 C47(H47), C48(H48), C51(H51), C52(H52), C54(H54), C55(H55), C56(H56), C57(H57),
  C59(H59), C60(H60), C9(H9), C10(H10), C11(H11), C12(H12), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C23(H23), C24(H24), C26(H26), C27(H27)
5.d Fitted hexagon refined as free rotating group:
 C50(C51,C52,C53,C54,C55)
5.e Idealised Me refined with riding coordinates:
 C61(H61A,H61B,H61C), C62(H62A,H62B,H62C)
5.f Idealised Me refined as rotating group:
 C49(H49A,H49B,H49C), C21(H21A,H21B,H21C), C28(H28A,H28B,H28C)
;
_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
O0AA O 0.33795(13) 0.59674(13) -0.17026(17) 0.0737(7) Uani 1 1 d . . . . .
O5 O 0.41309(14) 0.43481(13) 0.1223(2) 0.0818(7) Uani 1 1 d . . . . .
O6 O 0.19614(14) 0.59285(12) 0.19783(19) 0.0751(7) Uani 1 1 d . . . . .
O7 O 0.0022(7) 0.3857(6) -0.1051(9) 0.149(3) Uani 0.5 1 d D U P A 1
O8 O 0.0229(4) 0.3911(5) -0.1827(12) 0.124(2) Uani 0.5 1 d . U P B 2
C29 C 0.36895(15) 0.58605(15) 0.0362(2) 0.0492(7) Uani 1 1 d . . . . .
C30 C 0.33147(16) 0.52510(14) 0.0812(2) 0.0499(7) Uani 1 1 d . . . . .
C31 C 0.35707(18) 0.45239(16) 0.1110(3) 0.0577(8) Uani 1 1 d . . . . .
C32 C 0.30026(18) 0.40730(17) 0.1318(3) 0.0685(9) Uani 1 1 d . . . . .
H32A H 0.3096 0.3807 0.2037 0.082 Uiso 1 1 calc R . . . .
H32B H 0.2906 0.3745 0.0676 0.082 Uiso 1 1 calc R . . . .
C33 C 0.24314(17) 0.45653(16) 0.1407(3) 0.0595(8) Uani 1 1 d . . . . .
H33 H 0.2341 0.4589 0.2225 0.071 Uiso 1 1 calc R . . . .
C34 C 0.26953(16) 0.52735(15) 0.1057(2) 0.0513(7) Uani 1 1 d . . . . .
C35 C 0.22847(17) 0.59040(16) 0.1154(2) 0.0575(8) Uani 1 1 d . . . . .
C36 C 0.22506(17) 0.64855(16) 0.0282(3) 0.0583(8) Uani 1 1 d . . . . .
C37 C 0.1746(2) 0.69605(19) 0.0322(3) 0.0804(11) Uani 1 1 d . . . . .
H37 H 0.1468 0.6912 0.0899 0.097 Uiso 1 1 calc R . . . .
C38 C 0.1648(2) 0.7500(2) -0.0471(4) 0.0937(13) Uani 1 1 d . . . . .
H38 H 0.1312 0.7819 -0.0420 0.112 Uiso 1 1 calc R . . . .
C39 C 0.2048(2) 0.7565(2) -0.1338(4) 0.0845(12) Uani 1 1 d . . . . .
H39 H 0.1981 0.7928 -0.1880 0.101 Uiso 1 1 calc R . . . .
C40 C 0.25481(19) 0.70967(18) -0.1414(3) 0.0702(9) Uani 1 1 d . . . . .
H40 H 0.2813 0.7144 -0.2012 0.084 Uiso 1 1 calc R . . . .
C41 C 0.26606(17) 0.65526(16) -0.0603(2) 0.0562(8) Uani 1 1 d . . . . .
C42 C 0.32466(16) 0.61123(16) -0.0731(2) 0.0547(8) Uani 1 1 d . . . . .
C43 C 0.38254(14) 0.64364(15) 0.1287(2) 0.0472(7) Uani 1 1 d . . . . .
C44 C 0.39925(16) 0.62625(16) 0.2451(2) 0.0557(7) Uani 1 1 d . . . . .
H44 H 0.3956 0.5798 0.2690 0.067 Uiso 1 1 calc R . . . .
C45 C 0.42122(17) 0.67666(18) 0.3263(3) 0.0607(8) Uani 1 1 d . . . . .
H45 H 0.4323 0.6639 0.4040 0.073 Uiso 1 1 calc R . . . .
C46 C 0.42675(16) 0.74515(17) 0.2931(3) 0.0609(8) Uani 1 1 d . . . . .
H46 H 0.4422 0.7788 0.3478 0.073 Uiso 1 1 calc R . . . .
C47 C 0.40940(17) 0.76422(17) 0.1785(3) 0.0615(8) Uani 1 1 d . . . . .
H47 H 0.4121 0.8110 0.1559 0.074 Uiso 1 1 calc R . . . .
C48 C 0.38791(16) 0.71374(16) 0.0973(2) 0.0558(8) Uani 1 1 d . . . . .
H48 H 0.3768 0.7269 0.0198 0.067 Uiso 1 1 calc R . . . .
C49 C 0.43437(17) 0.56291(17) -0.0031(3) 0.0637(9) Uani 1 1 d . . . . .
H49A H 0.4624 0.5469 0.0636 0.096 Uiso 1 1 calc GR . . . .
H49B H 0.4541 0.6020 -0.0384 0.096 Uiso 1 1 calc GR . . . .
H49C H 0.4273 0.5254 -0.0589 0.096 Uiso 1 1 calc GR . . . .
C50 C 0.18178(15) 0.4386(2) 0.0656(3) 0.0802(6) Uani 1 1 d . . . . .
C51 C 0.1273(2) 0.4373(3) 0.1261(3) 0.0802(6) Uani 0.5 1 d G . P A 1
H51 H 0.1309 0.4487 0.2052 0.096 Uiso 0.5 1 calc R . P A 1
C52 C 0.06730(17) 0.4189(4) 0.0683(5) 0.0802(6) Uani 0.5 1 d G . P A 1
H52 H 0.0308 0.4180 0.1087 0.096 Uiso 0.5 1 calc R . P A 1
C53 C 0.0618(2) 0.4019(4) -0.0500(5) 0.0802(6) Uani 0.5 1 d G U P A 1
C54 C 0.1163(3) 0.4033(4) -0.1105(3) 0.0802(6) Uani 0.5 1 d G . P A 1
H54 H 0.1127 0.3919 -0.1896 0.096 Uiso 0.5 1 calc R . P A 1
C55 C 0.1763(2) 0.4216(3) -0.0527(3) 0.0802(6) Uani 0.5 1 d G . P A 1
H55 H 0.2128 0.4225 -0.0931 0.096 Uiso 0.5 1 calc R . P A 1
C56 C 0.1192(4) 0.4345(5) 0.0919(7) 0.0802(6) Uani 0.5 1 d . . P B 2
H56 H 0.1120 0.4421 0.1694 0.096 Uiso 0.5 1 calc R . P B 2
C57 C 0.0659(4) 0.4199(5) 0.0134(8) 0.0802(6) Uani 0.5 1 d . . P B 2
H57 H 0.0247 0.4182 0.0381 0.096 Uiso 0.5 1 calc R . P B 2
C58 C 0.0742(4) 0.4077(5) -0.1019(7) 0.0802(6) Uani 0.5 1 d . U P B 2
C59 C 0.1366(4) 0.4143(5) -0.1392(7) 0.0802(6) Uani 0.5 1 d . . P B 2
H59 H 0.1431 0.4091 -0.2176 0.096 Uiso 0.5 1 calc R . P B 2
C60 C 0.1885(4) 0.4288(5) -0.0537(7) 0.0802(6) Uani 0.5 1 d . . P B 2
H60 H 0.2298 0.4322 -0.0775 0.096 Uiso 0.5 1 calc R . P B 2
C61 C -0.0057(14) 0.3691(15) -0.2258(13) 0.222(8) Uani 0.5 1 d D U P A 1
H61A H -0.0168 0.4110 -0.2703 0.333 Uiso 0.5 1 calc R . P A 1
H61B H -0.0398 0.3351 -0.2410 0.333 Uiso 0.5 1 calc R . P A 1
H61C H 0.0340 0.3501 -0.2481 0.333 Uiso 0.5 1 calc R . P A 1
C62 C -0.0388(7) 0.3780(10) -0.139(2) 0.167(6) Uani 0.5 1 d . U P B 2
H62A H -0.0715 0.3714 -0.2041 0.251 Uiso 0.5 1 calc R . P B 2
H62B H -0.0501 0.4174 -0.0935 0.251 Uiso 0.5 1 calc R . P B 2
H62C H -0.0357 0.3365 -0.0915 0.251 Uiso 0.5 1 calc R . P B 2
O1 O 0.58654(13) 0.43187(13) 0.4350(3) 0.0825(7) Uani 1 1 d . . . . .
O2 O 0.80018(13) 0.59497(12) 0.58519(19) 0.0725(7) Uani 1 1 d . . . . .
O3 O 0.65651(14) 0.59403(14) 0.16264(18) 0.0812(8) Uani 1 1 d . . . . .
O4 O 0.9850(2) 0.3896(3) 0.3093(5) 0.1619(19) Uani 1 1 d . . . . .
C0AA C 0.64213(18) 0.45014(16) 0.4412(3) 0.0574(8) Uani 1 1 d . . . . .
C1 C 0.62625(16) 0.58224(15) 0.3574(2) 0.0524(7) Uani 1 1 d . . . . .
C1AA C 0.70004(16) 0.40635(17) 0.4818(3) 0.0632(8) Uani 1 1 d . . . . .
H1AA H 0.7101 0.3745 0.4203 0.076 Uiso 1 1 calc R . . . .
H1AB H 0.6920 0.3788 0.5498 0.076 Uiso 1 1 calc R . . . .
C2 C 0.66594(16) 0.52324(14) 0.4188(2) 0.0491(7) Uani 1 1 d . . . . .
C2AA C 0.72766(16) 0.52709(15) 0.4660(2) 0.0496(7) Uani 1 1 d . . . . .
C3AA C 0.76711(16) 0.59166(15) 0.4904(2) 0.0532(7) Uani 1 1 d . . . . .
C4AA C 0.76864(17) 0.64935(16) 0.4038(3) 0.0581(8) Uani 1 1 d . . . . .
C5AA C 0.75609(16) 0.45784(15) 0.5127(3) 0.0545(7) Uani 1 1 d . . . . .
H5AA H 0.7650 0.4609 0.5980 0.065 Uiso 1 1 calc R . . . .
C9 C 0.8185(2) 0.69891(18) 0.4273(3) 0.0753(10) Uani 1 1 d . . . . .
H9 H 0.8466 0.6953 0.4958 0.090 Uiso 1 1 calc R . . . .
C10 C 0.8262(2) 0.7529(2) 0.3499(4) 0.0922(13) Uani 1 1 d . . . . .
H10 H 0.8585 0.7864 0.3674 0.111 Uiso 1 1 calc R . . . .
C11 C 0.7863(2) 0.7572(2) 0.2475(4) 0.0924(14) Uani 1 1 d . . . . .
H11 H 0.7922 0.7931 0.1948 0.111 Uiso 1 1 calc R . . . .
C12 C 0.7376(2) 0.7089(2) 0.2215(3) 0.0787(11) Uani 1 1 d . . . . .
H12 H 0.7109 0.7125 0.1513 0.094 Uiso 1 1 calc R . . . .
C13 C 0.72754(17) 0.65419(16) 0.2996(3) 0.0590(8) Uani 1 1 d . . . . .
C14 C 0.66946(17) 0.60844(16) 0.2647(2) 0.0576(8) Uani 1 1 d . . . . .
C15 C 0.61050(15) 0.63999(14) 0.4420(2) 0.0476(7) Uani 1 1 d . . . . .
C16 C 0.60507(16) 0.71019(16) 0.4084(3) 0.0565(8) Uani 1 1 d . . . . .
H16 H 0.6167 0.7234 0.3356 0.068 Uiso 1 1 calc R . . . .
C17 C 0.58290(17) 0.76069(16) 0.4804(3) 0.0607(8) Uani 1 1 d . . . . .
H17 H 0.5799 0.8074 0.4561 0.073 Uiso 1 1 calc R . . . .
C18 C 0.56525(17) 0.74224(18) 0.5879(3) 0.0636(9) Uani 1 1 d . . . . .
H18 H 0.5496 0.7761 0.6362 0.076 Uiso 1 1 calc R . . . .
C19 C 0.57089(19) 0.67318(19) 0.6236(3) 0.0683(9) Uani 1 1 d . . . . .
H19 H 0.5597 0.6605 0.6969 0.082 Uiso 1 1 calc R . . . .
C20 C 0.59298(17) 0.62272(16) 0.5517(2) 0.0590(8) Uani 1 1 d . . . . .
H20 H 0.5962 0.5763 0.5770 0.071 Uiso 1 1 calc R . . . .
C21 C 0.56195(18) 0.55584(18) 0.2930(3) 0.0675(9) Uani 1 1 d . . . . .
H21A H 0.5703 0.5165 0.2443 0.101 Uiso 1 1 calc GR . . . .
H21B H 0.5420 0.5930 0.2452 0.101 Uiso 1 1 calc GR . . . .
H21C H 0.5335 0.5416 0.3491 0.101 Uiso 1 1 calc GR . . . .
C22 C 0.81822(16) 0.44073(16) 0.4617(3) 0.0578(8) Uani 1 1 d . . . . .
C23 C 0.8759(2) 0.4362(2) 0.5304(4) 0.0802(11) Uani 1 1 d . . . . .
H23 H 0.8770 0.4442 0.6104 0.096 Uiso 1 1 calc R . . . .
C24 C 0.9336(2) 0.4199(3) 0.4830(5) 0.1011(15) Uani 1 1 d . . . . .
H24 H 0.9728 0.4180 0.5307 0.121 Uiso 1 1 calc R . . . .
C25 C 0.9315(2) 0.4066(3) 0.3647(5) 0.1013(14) Uani 1 1 d . . . . .
C26 C 0.8747(3) 0.4129(3) 0.2956(5) 0.1155(18) Uani 1 1 d . . . . .
H26 H 0.8735 0.4059 0.2153 0.139 Uiso 1 1 calc R . . . .
C27 C 0.8188(2) 0.4295(2) 0.3435(3) 0.0876(12) Uani 1 1 d . . . . .
H27 H 0.7802 0.4332 0.2946 0.105 Uiso 1 1 calc R . . . .
C28 C 1.0403(4) 0.3706(5) 0.3786(9) 0.215(5) Uani 1 1 d . . . . .
H28A H 1.0726 0.3557 0.3301 0.322 Uiso 1 1 calc GR . . . .
H28B H 1.0306 0.3326 0.4290 0.322 Uiso 1 1 calc GR . . . .
H28C H 1.0562 0.4101 0.4252 0.322 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
O0AA C42 1.210(3) . ?
O5 C31 1.202(4) . ?
O6 C35 1.220(4) . ?
O7 C53 1.362(12) . ?
O7 C61 1.415(15) . ?
O8 C58 1.371(13) . ?
O8 C62 1.444(18) . ?
C29 C30 1.517(4) . ?
C29 C42 1.550(4) . ?
C29 C43 1.530(4) . ?
C29 C49 1.540(4) . ?
C30 C31 1.507(4) . ?
C30 C34 1.345(4) . ?
C31 C32 1.497(5) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 C33 1.522(5) . ?
C33 H33 0.9800 . ?
C33 C34 1.524(4) . ?
C33 C50 1.497(4) . ?
C34 C35 1.481(4) . ?
C35 C36 1.488(4) . ?
C36 C37 1.387(5) . ?
C36 C41 1.400(5) . ?
C37 H37 0.9300 . ?
C37 C38 1.372(5) . ?
C38 H38 0.9300 . ?
C38 C39 1.370(6) . ?
C39 H39 0.9300 . ?
C39 C40 1.377(6) . ?
C40 H40 0.9300 . ?
C40 C41 1.395(4) . ?
C41 C42 1.496(5) . ?
C43 C44 1.385(4) . ?
C43 C48 1.388(4) . ?
C44 H44 0.9300 . ?
C44 C45 1.380(4) . ?
C45 H45 0.9300 . ?
C45 C46 1.365(5) . ?
C46 H46 0.9300 . ?
C46 C47 1.376(5) . ?
C47 H47 0.9300 . ?
C47 C48 1.379(4) . ?
C48 H48 0.9300 . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?
C50 C51 1.3900 . ?
C50 C55 1.3900 . ?
C50 C56 1.366(9) . ?
C50 C60 1.406(10) . ?
C51 H51 0.9300 . ?
C51 C52 1.3900 . ?
C52 H52 0.9300 . ?
C52 C53 1.3900 . ?
C53 C54 1.3900 . ?
C54 H54 0.9300 . ?
C54 C55 1.3900 . ?
C55 H55 0.9300 . ?
C56 H56 0.9300 . ?
C56 C57 1.378(11) . ?
C57 H57 0.9300 . ?
C57 C58 1.374(11) . ?
C58 C59 1.412(11) . ?
C59 H59 0.9300 . ?
C59 C60 1.404(11) . ?
C60 H60 0.9300 . ?
C61 H61A 0.9600 . ?
C61 H61B 0.9600 . ?
C61 H61C 0.9600 . ?
C62 H62A 0.9600 . ?
C62 H62B 0.9600 . ?
C62 H62C 0.9600 . ?
O1 C0AA 1.199(4) . ?
O2 C3AA 1.224(4) . ?
O3 C14 1.206(4) . ?
O4 C25 1.377(6) . ?
O4 C28 1.372(9) . ?
C0AA C1AA 1.494(5) . ?
C0AA C2 1.506(4) . ?
C1 C2 1.519(4) . ?
C1 C14 1.547(4) . ?
C1 C15 1.525(4) . ?
C1 C21 1.538(5) . ?
C1AA H1AA 0.9700 . ?
C1AA H1AB 0.9700 . ?
C1AA C5AA 1.532(5) . ?
C2 C2AA 1.337(4) . ?
C2AA C3AA 1.485(4) . ?
C2AA C5AA 1.516(4) . ?
C3AA C4AA 1.483(4) . ?
C4AA C9 1.403(5) . ?
C4AA C13 1.396(5) . ?
C5AA H5AA 0.9800 . ?
C5AA C22 1.508(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.366(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.403(5) . ?
C13 C14 1.505(5) . ?
C15 C16 1.390(4) . ?
C15 C20 1.389(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.379(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.371(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.376(4) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.363(5) . ?
C22 C27 1.376(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.403(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.379(7) . ?
C25 C26 1.352(7) . ?
C26 H26 0.9300 . ?
C26 C27 1.373(6) . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 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
C53 O7 C61 121(2) . . ?
C58 O8 C62 117.3(17) . . ?
C30 C29 C42 103.4(2) . . ?
C30 C29 C43 111.9(2) . . ?
C30 C29 C49 112.5(2) . . ?
C43 C29 C42 113.0(2) . . ?
C43 C29 C49 107.8(3) . . ?
C49 C29 C42 108.3(2) . . ?
C31 C30 C29 126.6(3) . . ?
C34 C30 C29 125.7(3) . . ?
C34 C30 C31 107.6(3) . . ?
O5 C31 C30 126.3(3) . . ?
O5 C31 C32 126.3(3) . . ?
C32 C31 C30 107.3(3) . . ?
C31 C32 H32A 110.3 . . ?
C31 C32 H32B 110.3 . . ?
C31 C32 C33 106.9(3) . . ?
H32A C32 H32B 108.6 . . ?
C33 C32 H32A 110.3 . . ?
C33 C32 H32B 110.3 . . ?
C32 C33 H33 108.9 . . ?
C32 C33 C34 102.8(3) . . ?
C34 C33 H33 108.9 . . ?
C50 C33 C32 116.2(3) . . ?
C50 C33 H33 108.9 . . ?
C50 C33 C34 110.8(3) . . ?
C30 C34 C33 113.9(3) . . ?
C30 C34 C35 127.7(3) . . ?
C35 C34 C33 118.0(3) . . ?
O6 C35 C34 117.3(3) . . ?
O6 C35 C36 120.3(3) . . ?
C34 C35 C36 122.4(3) . . ?
C37 C36 C35 116.3(3) . . ?
C37 C36 C41 119.0(3) . . ?
C41 C36 C35 124.6(3) . . ?
C36 C37 H37 119.2 . . ?
C38 C37 C36 121.5(4) . . ?
C38 C37 H37 119.2 . . ?
C37 C38 H38 120.2 . . ?
C39 C38 C37 119.5(4) . . ?
C39 C38 H38 120.2 . . ?
C38 C39 H39 119.7 . . ?
C38 C39 C40 120.5(3) . . ?
C40 C39 H39 119.7 . . ?
C39 C40 H40 119.7 . . ?
C39 C40 C41 120.6(4) . . ?
C41 C40 H40 119.7 . . ?
C36 C41 C42 125.8(3) . . ?
C40 C41 C36 118.8(3) . . ?
C40 C41 C42 115.3(3) . . ?
O0AA C42 C29 120.2(3) . . ?
O0AA C42 C41 119.2(3) . . ?
C41 C42 C29 120.6(2) . . ?
C44 C43 C29 120.5(2) . . ?
C44 C43 C48 117.5(3) . . ?
C48 C43 C29 121.3(2) . . ?
C43 C44 H44 119.4 . . ?
C45 C44 C43 121.1(3) . . ?
C45 C44 H44 119.4 . . ?
C44 C45 H45 119.8 . . ?
C46 C45 C44 120.3(3) . . ?
C46 C45 H45 119.8 . . ?
C45 C46 H46 120.1 . . ?
C45 C46 C47 119.8(3) . . ?
C47 C46 H46 120.1 . . ?
C46 C47 H47 120.1 . . ?
C46 C47 C48 119.8(3) . . ?
C48 C47 H47 120.1 . . ?
C43 C48 H48 119.3 . . ?
C47 C48 C43 121.4(3) . . ?
C47 C48 H48 119.3 . . ?
C29 C49 H49A 109.5 . . ?
C29 C49 H49B 109.5 . . ?
C29 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C51 C50 C33 113.7(3) . . ?
C51 C50 C55 120.0 . . ?
C55 C50 C33 126.2(3) . . ?
C56 C50 C33 130.8(4) . . ?
C56 C50 C60 113.9(5) . . ?
C60 C50 C33 115.1(5) . . ?
C50 C51 H51 120.0 . . ?
C52 C51 C50 120.0 . . ?
C52 C51 H51 120.0 . . ?
C51 C52 H52 120.0 . . ?
C51 C52 C53 120.0 . . ?
C53 C52 H52 120.0 . . ?
O7 C53 C52 118.8(7) . . ?
O7 C53 C54 121.2(7) . . ?
C54 C53 C52 120.0 . . ?
C53 C54 H54 120.0 . . ?
C53 C54 C55 120.0 . . ?
C55 C54 H54 120.0 . . ?
C50 C55 H55 120.0 . . ?
C54 C55 C50 120.0 . . ?
C54 C55 H55 120.0 . . ?
C50 C56 H56 117.3 . . ?
C50 C56 C57 125.5(8) . . ?
C57 C56 H56 117.3 . . ?
C56 C57 H57 120.3 . . ?
C58 C57 C56 119.3(8) . . ?
C58 C57 H57 120.3 . . ?
O8 C58 C57 121.5(9) . . ?
O8 C58 C59 119.0(9) . . ?
C57 C58 C59 119.5(7) . . ?
C58 C59 H59 121.2 . . ?
C60 C59 C58 117.6(7) . . ?
C60 C59 H59 121.2 . . ?
C50 C60 H60 118.0 . . ?
C59 C60 C50 124.0(8) . . ?
C59 C60 H60 118.0 . . ?
O7 C61 H61A 109.5 . . ?
O7 C61 H61B 109.5 . . ?
O7 C61 H61C 109.5 . . ?
H61A C61 H61B 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
O8 C62 H62A 109.5 . . ?
O8 C62 H62B 109.5 . . ?
O8 C62 H62C 109.5 . . ?
H62A C62 H62B 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
C28 O4 C25 117.3(6) . . ?
O1 C0AA C1AA 126.4(3) . . ?
O1 C0AA C2 126.0(3) . . ?
C1AA C0AA C2 107.4(3) . . ?
C2 C1 C14 103.4(2) . . ?
C2 C1 C15 112.2(2) . . ?
C2 C1 C21 112.4(3) . . ?
C15 C1 C14 112.8(2) . . ?
C15 C1 C21 107.9(3) . . ?
C21 C1 C14 108.1(2) . . ?
C0AA C1AA H1AA 110.5 . . ?
C0AA C1AA H1AB 110.5 . . ?
C0AA C1AA C5AA 106.3(3) . . ?
H1AA C1AA H1AB 108.7 . . ?
C5AA C1AA H1AA 110.5 . . ?
C5AA C1AA H1AB 110.5 . . ?
C0AA C2 C1 126.1(3) . . ?
C2AA C2 C0AA 107.4(3) . . ?
C2AA C2 C1 126.5(3) . . ?
C2 C2AA C3AA 127.3(3) . . ?
C2 C2AA C5AA 114.5(3) . . ?
C3AA C2AA C5AA 117.7(3) . . ?
O2 C3AA C2AA 117.0(3) . . ?
O2 C3AA C4AA 120.5(3) . . ?
C4AA C3AA C2AA 122.4(3) . . ?
C9 C4AA C3AA 115.8(3) . . ?
C13 C4AA C3AA 124.7(3) . . ?
C13 C4AA C9 119.3(3) . . ?
C1AA C5AA H5AA 109.0 . . ?
C2AA C5AA C1AA 102.5(3) . . ?
C2AA C5AA H5AA 109.0 . . ?
C22 C5AA C1AA 115.6(3) . . ?
C22 C5AA C2AA 111.5(2) . . ?
C22 C5AA H5AA 109.0 . . ?
C4AA C9 H9 119.7 . . ?
C10 C9 C4AA 120.7(4) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.9(4) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.7(4) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.8(4) . . ?
C13 C12 H12 119.6 . . ?
C4AA C13 C12 118.6(4) . . ?
C4AA C13 C14 126.0(3) . . ?
C12 C13 C14 115.3(3) . . ?
O3 C14 C1 120.8(3) . . ?
O3 C14 C13 118.5(3) . . ?
C13 C14 C1 120.6(2) . . ?
C16 C15 C1 122.0(2) . . ?
C20 C15 C1 120.3(3) . . ?
C20 C15 C16 117.3(3) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.6(3) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.1(3) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.3(3) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 H20 119.4 . . ?
C19 C20 C15 121.1(3) . . ?
C19 C20 H20 119.4 . . ?
C1 C21 H21A 109.5 . . ?
C1 C21 H21B 109.5 . . ?
C1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C5AA 121.5(3) . . ?
C23 C22 C27 117.5(4) . . ?
C27 C22 C5AA 121.1(3) . . ?
C22 C23 H23 119.3 . . ?
C22 C23 C24 121.4(4) . . ?
C24 C23 H23 119.3 . . ?
C23 C24 H24 120.5 . . ?
C25 C24 C23 119.0(4) . . ?
C25 C24 H24 120.5 . . ?
O4 C25 C24 123.8(5) . . ?
C26 C25 O4 116.3(5) . . ?
C26 C25 C24 119.8(4) . . ?
C25 C26 H26 119.9 . . ?
C25 C26 C27 120.2(5) . . ?
C27 C26 H26 119.9 . . ?
C22 C27 H27 119.0 . . ?
C26 C27 C22 122.0(4) . . ?
C26 C27 H27 119.0 . . ?
O4 C28 H28A 109.5 . . ?
O4 C28 H28B 109.5 . . ?
O4 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_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_vlhcphot7
_database_code_depnum_ccdc_archive 'CCDC 1992516'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;Spectropole, Aix Marseille University
France
;
_audit_update_record             
;
2020-03-24 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;
_audit_creation_date             2017-11-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 O2'
_chemical_formula_sum            'C15 H12 O2'
_chemical_formula_weight         224.25
_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 0.0181 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/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                   7.47760(10)
_cell_length_b                   10.63950(10)
_cell_length_c                   14.0595(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.8290(10)
_cell_angle_gamma                90
_cell_volume                     1108.12(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5301
_cell_measurement_temperature    293
_cell_measurement_theta_max      71.0460
_cell_measurement_theta_min      4.1480
_shelx_estimated_absorpt_T_max   0.848
_shelx_estimated_absorpt_T_min   0.765
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.18b (Rigaku Oxford Diffraction, 2015)
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    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6943
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.846
_diffrn_reflns_theta_min         5.231
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -92.00 -10.00   1.00    1.00    --  -17.77 -38.00 -60.00   82
  2  ω    -79.00   6.00   1.00    1.00    --  -17.77 -77.00 120.00   85
  3  ω    -28.00  56.00   1.00    1.00    --  -17.77  38.00  30.00   84
  4  ω     46.00  75.00   1.00    1.00    --   17.77-131.00 -91.00   29
  5  ω      2.00  43.00   1.00    1.00    --   17.77 -99.00-180.00   41
  6  ω     29.00  57.00   1.00    1.00    --   17.77 -99.00 120.00   28
  7  ω     61.00  88.00   1.00    1.00    --   17.77 178.00 -30.00   27
  8  ω     23.00 102.00   1.00    2.00    --  101.41 -94.00-150.00   79
  9  ω    130.00 156.00   1.00    2.00    --  101.41 125.00  90.00   26
 10  ω     81.00 125.00   1.00    2.00    --  101.41 -30.00 -60.00   44
 11  ω     77.00 159.00   1.00    2.00    --  101.41  45.00 -90.00   82
 12  ω     72.00 107.00   1.00    2.00    --  101.41 -94.00  90.00   35
 13  ω     33.00 125.00   1.00    2.00    --  101.41 -45.00-150.00   92
 14  ω     75.00 170.00   1.00    2.00    --  101.41  30.00-180.00   95
 15  ω     80.00 106.00   1.00    2.00    --  101.41  30.00 150.00   26
 16  ω     32.00 108.00   1.00    2.00    --  101.41 -94.00  30.00   76
 17  ω     41.00 119.00   1.00    2.00    --  101.41 -45.00  60.00   78
 18  ω     63.00 101.00   1.00    2.00    --  101.41 -94.00 -60.00   38
 19  ω    104.00 155.00   1.00    2.00    --  101.41 125.00-150.00   51
 20  ω     27.00  56.00   1.00    2.00    --  101.41 -30.00 -60.00   29
 21  ω     28.00  57.00   1.00    2.00    --  101.41-125.00 -90.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1271771000
_diffrn_orient_matrix_UB_12      -0.0780643000
_diffrn_orient_matrix_UB_13      -0.0726431000
_diffrn_orient_matrix_UB_21      -0.0857357000
_diffrn_orient_matrix_UB_22      0.1218828000
_diffrn_orient_matrix_UB_23      -0.0444198000
_diffrn_orient_matrix_UB_31      0.1404565000
_diffrn_orient_matrix_UB_32      0.0036765000
_diffrn_orient_matrix_UB_33      -0.0705948000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1997
_reflns_number_total             2103
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_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         0.345
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2103
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.163
_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)+(0.0739P)²+0.2254P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1302
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.12541(13) 0.63927(10) 0.66008(7) 0.0408(3) Uani 1 1 d . . . . .
O2 O 0.66911(15) 0.60771(11) 0.81700(8) 0.0511(3) Uani 1 1 d . . . . .
C1 C 0.28466(16) 0.58850(12) 0.63188(9) 0.0307(3) Uani 1 1 d . . . . .
C2 C 0.26633(18) 0.45667(14) 0.58117(10) 0.0375(3) Uani 1 1 d . . . . .
H2 H 0.294125 0.455745 0.515038 0.045 Uiso 1 1 calc R . . . .
C3 C 0.0913(2) 0.39584(16) 0.59521(12) 0.0482(4) Uani 1 1 d . . . . .
H3 H 0.043153 0.332469 0.553874 0.058 Uiso 1 1 calc R . . . .
C4 C 0.0056(2) 0.43250(18) 0.66647(13) 0.0531(4) Uani 1 1 d . . . . .
H4 H -0.096862 0.390057 0.679766 0.064 Uiso 1 1 calc R . . . .
C5 C 0.0762(2) 0.54409(17) 0.72594(11) 0.0477(4) Uani 1 1 d . . . . .
H5 H -0.015123 0.576168 0.763514 0.057 Uiso 1 1 calc R . . . .
C6 C 0.2569(2) 0.51762(17) 0.79158(10) 0.0468(4) Uani 1 1 d . . . . .
H6A H 0.279382 0.579435 0.842519 0.056 Uiso 1 1 calc R . . . .
H6B H 0.257934 0.434246 0.819556 0.056 Uiso 1 1 calc R . . . .
C7 C 0.39430(18) 0.52855(13) 0.72091(9) 0.0336(3) Uani 1 1 d . . . . .
C8 C 0.4224(2) 0.41080(13) 0.65857(11) 0.0408(4) Uani 1 1 d . . . . .
H8A H 0.397091 0.331863 0.688567 0.049 Uiso 1 1 calc R . . . .
H8B H 0.539340 0.408371 0.636003 0.049 Uiso 1 1 calc R . . . .
C9 C 0.56051(18) 0.60964(13) 0.74438(10) 0.0352(3) Uani 1 1 d . . . . .
C10 C 0.56645(18) 0.69364(13) 0.66032(9) 0.0342(3) Uani 1 1 d . . . . .
C11 C 0.7030(2) 0.77531(15) 0.64234(11) 0.0439(4) Uani 1 1 d . . . . .
H11 H 0.809823 0.780971 0.684578 0.053 Uiso 1 1 calc R . . . .
C12 C 0.6761(2) 0.84782(15) 0.56019(12) 0.0490(4) Uani 1 1 d . . . . .
H12 H 0.765934 0.902864 0.546733 0.059 Uiso 1 1 calc R . . . .
C13 C 0.5161(2) 0.83940(14) 0.49743(11) 0.0448(4) Uani 1 1 d . . . . .
H13 H 0.500327 0.889500 0.442726 0.054 Uiso 1 1 calc R . . . .
C14 C 0.37956(19) 0.75792(13) 0.51464(10) 0.0373(3) Uani 1 1 d . . . . .
H14 H 0.272831 0.752798 0.472291 0.045 Uiso 1 1 calc R . . . .
C15 C 0.40632(17) 0.68420(12) 0.59671(9) 0.0313(3) 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
O1 C1 1.4127(15) . ?
O1 C5 1.4529(18) . ?
O2 C9 1.2152(17) . ?
C1 C2 1.5708(18) . ?
C1 C7 1.5382(17) . ?
C1 C15 1.4937(18) . ?
C2 H2 0.9800 . ?
C2 C3 1.497(2) . ?
C2 C8 1.5617(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.320(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.506(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.555(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.5278(19) . ?
C7 C8 1.5596(19) . ?
C7 C9 1.512(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.4872(19) . ?
C10 C11 1.390(2) . ?
C10 C15 1.3971(18) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.3870(19) . ?

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
C1 O1 C5 102.04(10) . . ?
O1 C1 C2 116.36(11) . . ?
O1 C1 C7 107.84(10) . . ?
O1 C1 C15 114.01(11) . . ?
C7 C1 C2 90.17(10) . . ?
C15 C1 C2 118.54(10) . . ?
C15 C1 C7 105.72(10) . . ?
C1 C2 H2 115.0 . . ?
C3 C2 C1 110.49(12) . . ?
C3 C2 H2 115.0 . . ?
C3 C2 C8 110.91(12) . . ?
C8 C2 C1 87.25(9) . . ?
C8 C2 H2 115.0 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.73(15) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.00(14) . . ?
C5 C4 H4 120.5 . . ?
O1 C5 C4 107.20(12) . . ?
O1 C5 H5 110.9 . . ?
O1 C5 C6 103.27(12) . . ?
C4 C5 H5 110.9 . . ?
C4 C5 C6 113.42(14) . . ?
C6 C5 H5 110.9 . . ?
C5 C6 H6A 111.4 . . ?
C5 C6 H6B 111.4 . . ?
H6A C6 H6B 109.2 . . ?
C7 C6 C5 101.96(11) . . ?
C7 C6 H6A 111.4 . . ?
C7 C6 H6B 111.4 . . ?
C1 C7 C8 88.48(10) . . ?
C6 C7 C1 103.28(11) . . ?
C6 C7 C8 117.29(13) . . ?
C9 C7 C1 105.79(11) . . ?
C9 C7 C6 120.46(12) . . ?
C9 C7 C8 114.28(11) . . ?
C2 C8 H8A 113.7 . . ?
C2 C8 H8B 113.7 . . ?
C7 C8 C2 89.73(10) . . ?
C7 C8 H8A 113.7 . . ?
C7 C8 H8B 113.7 . . ?
H8A C8 H8B 110.9 . . ?
O2 C9 C7 127.53(13) . . ?
O2 C9 C10 126.09(13) . . ?
C10 C9 C7 106.39(11) . . ?
C11 C10 C9 128.49(12) . . ?
C11 C10 C15 121.02(13) . . ?
C15 C10 C9 110.47(12) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 C10 118.31(14) . . ?
C12 C11 H11 120.8 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.67(14) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.38(14) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 120.9 . . ?
C13 C14 C15 118.22(13) . . ?
C15 C14 H14 120.9 . . ?
C10 C15 C1 110.16(11) . . ?
C14 C15 C1 129.46(12) . . ?
C14 C15 C10 120.38(13) . . ?

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
O1 C1 C2 C3 -14.51(16) . . . . ?
O1 C1 C2 C8 -125.82(11) . . . . ?
O1 C1 C7 C6 15.90(14) . . . . ?
O1 C1 C7 C8 133.62(11) . . . . ?
O1 C1 C7 C9 -111.55(11) . . . . ?
O1 C1 C15 C10 112.94(12) . . . . ?
O1 C1 C15 C14 -67.24(17) . . . . ?
O1 C5 C6 C7 -36.43(15) . . . . ?
O2 C9 C10 C11 7.8(2) . . . . ?
O2 C9 C10 C15 -170.67(14) . . . . ?
C1 O1 C5 C4 -72.96(13) . . . . ?
C1 O1 C5 C6 47.08(14) . . . . ?
C1 C2 C3 C4 -20.7(2) . . . . ?
C1 C2 C8 C7 15.52(10) . . . . ?
C1 C7 C8 C2 -15.85(10) . . . . ?
C1 C7 C9 O2 167.87(14) . . . . ?
C1 C7 C9 C10 -12.21(13) . . . . ?
C2 C1 C7 C6 -101.96(11) . . . . ?
C2 C1 C7 C8 15.75(10) . . . . ?
C2 C1 C7 C9 130.58(11) . . . . ?
C2 C1 C15 C10 -104.34(13) . . . . ?
C2 C1 C15 C14 75.48(18) . . . . ?
C2 C3 C4 C5 6.3(2) . . . . ?
C3 C2 C8 C7 -95.38(13) . . . . ?
C3 C4 C5 O1 42.9(2) . . . . ?
C3 C4 C5 C6 -70.48(19) . . . . ?
C4 C5 C6 C7 79.25(15) . . . . ?
C5 O1 C1 C2 59.88(13) . . . . ?
C5 O1 C1 C7 -39.50(13) . . . . ?
C5 O1 C1 C15 -156.55(12) . . . . ?
C5 C6 C7 C1 12.51(15) . . . . ?
C5 C6 C7 C8 -82.72(15) . . . . ?
C5 C6 C7 C9 130.11(14) . . . . ?
C6 C7 C8 C2 88.33(13) . . . . ?
C6 C7 C9 O2 51.6(2) . . . . ?
C6 C7 C9 C10 -128.52(13) . . . . ?
C7 C1 C2 C3 95.58(12) . . . . ?
C7 C1 C2 C8 -15.74(10) . . . . ?
C7 C1 C15 C10 -5.33(14) . . . . ?
C7 C1 C15 C14 174.49(13) . . . . ?
C7 C9 C10 C11 -172.13(13) . . . . ?
C7 C9 C10 C15 9.41(14) . . . . ?
C8 C2 C3 C4 74.30(19) . . . . ?
C8 C7 C9 O2 -96.54(17) . . . . ?
C8 C7 C9 C10 83.38(13) . . . . ?
C9 C7 C8 C2 -122.51(12) . . . . ?
C9 C10 C11 C12 -177.86(14) . . . . ?
C9 C10 C15 C1 -2.48(15) . . . . ?
C9 C10 C15 C14 177.68(12) . . . . ?
C10 C11 C12 C13 0.2(2) . . . . ?
C11 C10 C15 C1 178.92(12) . . . . ?
C11 C10 C15 C14 -0.9(2) . . . . ?
C11 C12 C13 C14 -0.4(2) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 C1 -179.14(13) . . . . ?
C13 C14 C15 C10 0.7(2) . . . . ?
C15 C1 C2 C3 -156.36(12) . . . . ?
C15 C1 C2 C8 92.32(13) . . . . ?
C15 C1 C7 C6 138.22(11) . . . . ?
C15 C1 C7 C8 -104.06(11) . . . . ?
C15 C1 C7 C9 10.77(13) . . . . ?
C15 C10 C11 C12 0.5(2) . . . . ?

_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 1.252
_oxdiff_exptl_absorpt_empirical_full_min 0.642


