# 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_nb184f5
_database_code_depnum_ccdc_archive 'CCDC 1954293'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;Spectropole de Marseille
France
;
_audit_update_record             
;
2019-09-17 deposited with the CCDC.	2020-03-12 downloaded from the CCDC.
;
_audit_creation_date             2018-10-04
_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         'C11 H14 O3'
_chemical_formula_sum            'C11 H14 O3'
_chemical_formula_weight         194.22
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c11 h14 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.7787(6)
_cell_length_b                   8.8337(8)
_cell_length_c                   20.223(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1032.34(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3710
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.8800
_cell_measurement_theta_min      4.1890
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63209
_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    1.250
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7685
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.416
_diffrn_reflns_theta_min         3.062
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  33.00   1.00   20.00    --   -7.86 -99.00  60.00   53
  2  ω    -64.00  37.00   1.00   20.00    --    8.41 -57.00 120.00  101
  3  ω    -64.00  37.00   1.00   20.00    --    8.41 -57.00-180.00  101
  4  ω    -20.00  10.00   1.00   20.00    --    8.41 -99.00   0.00   30
;
_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      0.1160688000
_diffrn_orient_matrix_UB_12      0.0259892000
_diffrn_orient_matrix_UB_13      -0.0012848000
_diffrn_orient_matrix_UB_21      0.0003730000
_diffrn_orient_matrix_UB_22      0.0083316000
_diffrn_orient_matrix_UB_23      0.0348491000
_diffrn_orient_matrix_UB_31      0.0400255000
_diffrn_orient_matrix_UB_32      -0.0755841000
_diffrn_orient_matrix_UB_33      0.0034280000
_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         0.608
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.790
_reflns_number_gt                1865
_reflns_number_total             2232
_reflns_odcompleteness_completeness 99.63
_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 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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 613 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.102
_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)+(0.0564P)²+0.0350P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1085
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H7BC)=Sof(H7BD)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C13)=Sof(H13A)=Sof(H13B)=
 Sof(H13C)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=1-FVAR(1)
 Sof(H7AB)=Sof(H7AA)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(C11)=Sof(H11A)=Sof(H11B)=
 Sof(H11C)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7AB,H7AA), C7(H7BC,H7BD), C8(H8A,H8B), C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2)
3.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C)
;
_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 0.1216(2) 0.45528(16) 0.65043(7) 0.0511(4) Uani 1 1 d . . . . .
O2 O 0.5241(4) 0.5444(2) 0.49129(9) 0.0839(6) Uani 1 1 d . . . . .
O3 O 0.2921(3) 0.24276(18) 0.67283(8) 0.0682(5) Uani 1 1 d . . . . .
C1 C 0.0875(4) 0.5858(2) 0.61402(11) 0.0499(5) Uani 1 1 d . . . . .
C2 C 0.2192(4) 0.6173(2) 0.56202(11) 0.0568(6) Uani 1 1 d . . . . .
H2 H 0.192351 0.706324 0.538670 0.068 Uiso 1 1 calc R . . . .
C3 C 0.4029(4) 0.5180(3) 0.54055(11) 0.0541(6) Uani 1 1 d . . . . .
C4 C 0.4354(3) 0.3834(2) 0.58008(9) 0.0453(5) Uani 1 1 d . . . . .
C5 C 0.2943(3) 0.3605(2) 0.63184(9) 0.0446(5) Uani 1 1 d . . . . .
C6 C -0.1078(4) 0.6758(3) 0.64042(14) 0.0689(7) Uani 1 1 d . . . . .
H6A H -0.246809 0.616446 0.638936 0.103 Uiso 1 1 calc GR . . . .
H6B H -0.127489 0.765359 0.614125 0.103 Uiso 1 1 calc GR . . . .
H6C H -0.075624 0.704016 0.685339 0.103 Uiso 1 1 calc GR . . . .
C7 C 0.6148(5) 0.2680(3) 0.56332(12) 0.0641(6) Uani 1 1 d . . . . .
H7AB H 0.760716 0.293924 0.584135 0.077 Uiso 0.684(5) 1 calc R . P A 1
H7AA H 0.638185 0.264446 0.515845 0.077 Uiso 0.684(5) 1 calc R . P A 1
H7BC H 0.741728 0.315213 0.539670 0.077 Uiso 0.316(5) 1 calc R . P A 2
H7BD H 0.548510 0.190102 0.535302 0.077 Uiso 0.316(5) 1 calc R . P A 2
C8 C 0.5274(6) 0.1088(3) 0.58924(16) 0.0537(9) Uani 0.684(5) 1 d . . P A 1
H8A H 0.392098 0.077176 0.564417 0.064 Uiso 0.684(5) 1 calc R . P A 1
H8B H 0.647487 0.033268 0.583272 0.064 Uiso 0.684(5) 1 calc R . P A 1
C9 C 0.7031(14) 0.1977(9) 0.6282(4) 0.062(2) Uani 0.316(5) 1 d . . P A 2
H9A H 0.769769 0.274405 0.656747 0.074 Uiso 0.316(5) 1 calc R . P A 2
H9B H 0.818504 0.120502 0.619531 0.074 Uiso 0.316(5) 1 calc R . P A 2
C10 C 0.4673(4) 0.1230(3) 0.66198(11) 0.0559(6) Uani 1 1 d . . . . .
C11 C 0.6547(8) 0.1594(7) 0.7059(2) 0.0812(14) Uani 0.684(5) 1 d . . P A 1
H11A H 0.717852 0.256282 0.694214 0.122 Uiso 0.684(5) 1 calc GR . P A 1
H11B H 0.772908 0.083524 0.702401 0.122 Uiso 0.684(5) 1 calc GR . P A 1
H11C H 0.598352 0.162835 0.750578 0.122 Uiso 0.684(5) 1 calc GR . P A 1
C12 C 0.3353(9) -0.0255(4) 0.6823(3) 0.0852(15) Uani 0.684(5) 1 d . . P A 1
H12A H 0.279790 -0.015805 0.726837 0.128 Uiso 0.684(5) 1 calc GR . P A 1
H12B H 0.438787 -0.110277 0.679487 0.128 Uiso 0.684(5) 1 calc GR . P A 1
H12C H 0.206844 -0.041044 0.652992 0.128 Uiso 0.684(5) 1 calc GR . P A 1
C13 C 0.3556(17) 0.0223(10) 0.6232(5) 0.078(3) Uani 0.316(5) 1 d . . P A 2
H13A H 0.229405 -0.021576 0.647448 0.117 Uiso 0.316(5) 1 calc GR . P A 2
H13B H 0.461015 -0.056050 0.610000 0.117 Uiso 0.316(5) 1 calc GR . P A 2
H13C H 0.296910 0.072866 0.584718 0.117 Uiso 0.316(5) 1 calc GR . P A 2
C14 C 0.560(2) 0.0660(11) 0.7309(4) 0.075(3) Uani 0.316(5) 1 d . . P A 2
H14A H 0.636791 0.147546 0.753183 0.112 Uiso 0.316(5) 1 calc GR . P A 2
H14B H 0.666345 -0.015875 0.724163 0.112 Uiso 0.316(5) 1 calc GR . P A 2
H14C H 0.432007 0.031529 0.757277 0.112 Uiso 0.316(5) 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.382(2) . ?
O1 C5 1.356(2) . ?
O2 C3 1.240(3) . ?
O3 C5 1.330(2) . ?
O3 C10 1.481(3) . ?
C1 C2 1.328(3) . ?
C1 C6 1.480(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.444(3) . ?
C3 C4 1.445(3) . ?
C4 C5 1.342(3) . ?
C4 C7 1.493(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7AB 0.9700 . ?
C7 H7AA 0.9700 . ?
C7 H7BC 0.9700 . ?
C7 H7BD 0.9700 . ?
C7 C8 1.584(4) . ?
C7 C9 1.538(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C10 1.517(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.661(8) . ?
C10 C11 1.438(5) . ?
C10 C12 1.572(5) . ?
C10 C13 1.350(9) . ?
C10 C14 1.575(8) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C5 O1 C1 118.19(16) . . ?
C5 O3 C10 117.38(16) . . ?
O1 C1 C6 111.39(19) . . ?
C2 C1 O1 121.00(19) . . ?
C2 C1 C6 127.6(2) . . ?
C1 C2 H2 118.9 . . ?
C1 C2 C3 122.1(2) . . ?
C3 C2 H2 118.9 . . ?
O2 C3 C2 122.8(2) . . ?
O2 C3 C4 121.7(2) . . ?
C2 C3 C4 115.43(19) . . ?
C3 C4 C7 121.79(19) . . ?
C5 C4 C3 118.45(19) . . ?
C5 C4 C7 119.72(18) . . ?
O3 C5 O1 107.64(16) . . ?
O3 C5 C4 127.56(18) . . ?
C4 C5 O1 124.78(17) . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7AB 110.1 . . ?
C4 C7 H7AA 110.1 . . ?
C4 C7 H7BC 110.1 . . ?
C4 C7 H7BD 110.1 . . ?
C4 C7 C8 108.07(19) . . ?
C4 C7 C9 108.2(3) . . ?
H7AB C7 H7AA 108.4 . . ?
H7BC C7 H7BD 108.4 . . ?
C8 C7 H7AB 110.1 . . ?
C8 C7 H7AA 110.1 . . ?
C9 C7 H7BC 110.1 . . ?
C9 C7 H7BD 110.1 . . ?
C7 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.3 . . ?
C10 C8 C7 108.7(2) . . ?
C10 C8 H8A 110.0 . . ?
C10 C8 H8B 110.0 . . ?
C7 C9 H9A 111.0 . . ?
C7 C9 H9B 111.0 . . ?
C7 C9 C10 103.8(5) . . ?
H9A C9 H9B 109.0 . . ?
C10 C9 H9A 111.0 . . ?
C10 C9 H9B 111.0 . . ?
O3 C10 C8 111.06(19) . . ?
O3 C10 C9 109.7(3) . . ?
O3 C10 C12 103.0(2) . . ?
O3 C10 C14 109.2(4) . . ?
C8 C10 C12 107.2(3) . . ?
C11 C10 O3 105.2(2) . . ?
C11 C10 C8 116.5(3) . . ?
C11 C10 C12 113.0(3) . . ?
C13 C10 O3 103.3(4) . . ?
C13 C10 C9 114.6(6) . . ?
C13 C10 C14 117.7(6) . . ?
C14 C10 C9 102.3(5) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_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 1.885
_oxdiff_exptl_absorpt_empirical_full_min 0.519
####################################################################### 
# 
# 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_nb217
_database_code_depnum_ccdc_archive 'CCDC 1954295'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;Spectropole de Marseille
France
;
_audit_update_record             
;
2019-09-17 deposited with the CCDC.	2020-03-12 downloaded from the CCDC.
;
_audit_creation_date             2018-10-04
_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         'C9 H12 O3'
_chemical_formula_sum            'C9 H12 O3'
_chemical_formula_weight         168.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c9 h12 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      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                   9.9577(7)
_cell_length_b                   6.3420(4)
_cell_length_c                   14.3464(12)
_cell_angle_alpha                90
_cell_angle_beta                 98.748(8)
_cell_angle_gamma                90
_cell_volume                     895.46(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3789
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.1780
_cell_measurement_theta_min      4.1270
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.946
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63121
_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    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9442
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.439
_diffrn_reflns_theta_min         3.519
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  68.00   1.00   30.00    --   -7.86  77.00 -30.00  108
  2  ω    -20.00  33.00   1.00   30.00    --   -7.86 -99.00-150.00   53
  3  ω    -16.00  83.00   1.00   30.00    --    8.41  38.00   0.00   99
  4  ω      0.00  30.00   1.00   30.00    --    8.41 -38.00-150.00   30
  5  ω     15.00  49.00   1.00   30.00    --    8.41 -99.00  90.00   34
  6  ω    -63.00  33.00   1.00   30.00    --    8.41 -38.00-180.00   96
;
_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      -0.0304926000
_diffrn_orient_matrix_UB_12      -0.0154074000
_diffrn_orient_matrix_UB_13      -0.0474935000
_diffrn_orient_matrix_UB_21      0.0652564000
_diffrn_orient_matrix_UB_22      -0.0031835000
_diffrn_orient_matrix_UB_23      -0.0140487000
_diffrn_orient_matrix_UB_31      0.0023805000
_diffrn_orient_matrix_UB_32      -0.1107444000
_diffrn_orient_matrix_UB_33      0.0069799000
_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                1438
_reflns_number_total             1988
_reflns_odcompleteness_completeness 99.64
_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 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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1988
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.110
_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)+(0.0527P)²+0.3515P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1458
_refine_ls_wR_factor_ref         0.1573
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C6(0.5) H6A(0.5) H6B(0.5) C7(0.5) H7A(0.5) H7B(0.5) H8AA(0.5)
 H8AB(0.5) H8BC(0.5) H8BD(0.5) C9(0.5) H9A(0.5) H9B(0.5) H9C(0.5) C10(0.5)
 H10A(0.5) H10B(0.5) H10C(0.5) C11(0.5) H11A(0.5) H11B(0.5) H11C(0.5) C12(0.5)
 H12C(0.5) H12B(0.5) H12A(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C8(H8AA,H8AB), C8(H8BC,H8BD)
3.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12C,H12B,H12A)
;
_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 0.16594(16) 0.4141(2) 0.45812(10) 0.0708(5) Uani 1 1 d . . . . .
O2 O 0.2476(2) 0.0888(3) 0.44432(13) 0.0941(6) Uani 1 1 d . . . . .
O3 O 0.36385(16) 0.6347(2) 0.66187(11) 0.0766(5) Uani 1 1 d . . . . .
C1 C 0.2540(2) 0.2532(3) 0.48756(15) 0.0634(6) Uani 1 1 d . . . . .
C2 C 0.1950(2) 0.5901(4) 0.52098(16) 0.0688(6) Uani 1 1 d . . . . .
H2A H 0.117196 0.625269 0.551222 0.083 Uiso 1 1 calc R . . . .
H2B H 0.221172 0.713181 0.487802 0.083 Uiso 1 1 calc R . . . .
C3 C 0.30999(19) 0.5125(3) 0.59079(13) 0.0522(5) Uani 1 1 d . . . . .
C4 C 0.3442(2) 0.3185(3) 0.57125(14) 0.0543(5) Uani 1 1 d . . . . .
C5 C 0.47387(19) 0.5339(3) 0.72929(15) 0.0584(5) Uani 1 1 d . . . . .
C6 C 0.4547(5) 0.2831(7) 0.7354(3) 0.0660(11) Uani 0.5 1 d . . P A 1
H6A H 0.369585 0.249434 0.757069 0.079 Uiso 0.5 1 calc R . P A 1
H6B H 0.528626 0.220948 0.778503 0.079 Uiso 0.5 1 calc R . P A 1
C7 C 0.5552(4) 0.3785(7) 0.6758(3) 0.0638(11) Uani 0.5 1 d . . P A 2
H7A H 0.629252 0.317259 0.719119 0.077 Uiso 0.5 1 calc R . P A 2
H7B H 0.593355 0.452785 0.626868 0.077 Uiso 0.5 1 calc R . P A 2
C8 C 0.4549(3) 0.1972(4) 0.6301(2) 0.0843(8) Uani 1 1 d . . . . .
H8AA H 0.541810 0.223335 0.609637 0.101 Uiso 0.5 1 calc R . P A 1
H8AB H 0.436188 0.047111 0.626504 0.101 Uiso 0.5 1 calc R . P A 1
H8BC H 0.500119 0.103010 0.591643 0.101 Uiso 0.5 1 calc R . P A 2
H8BD H 0.419682 0.115876 0.678338 0.101 Uiso 0.5 1 calc R . P A 2
C9 C 0.5930(5) 0.5959(9) 0.7018(5) 0.0921(18) Uani 0.5 1 d . . P A 1
H9A H 0.595905 0.746993 0.698919 0.138 Uiso 0.5 1 calc GR . P A 1
H9B H 0.599056 0.538427 0.640641 0.138 Uiso 0.5 1 calc GR . P A 1
H9C H 0.667898 0.545787 0.746395 0.138 Uiso 0.5 1 calc GR . P A 1
C10 C 0.4497(7) 0.6123(11) 0.8306(4) 0.102(2) Uani 0.5 1 d . . P A 1
H10A H 0.518637 0.554379 0.877755 0.153 Uiso 0.5 1 calc GR . P A 1
H10B H 0.361943 0.566362 0.842310 0.153 Uiso 0.5 1 calc GR . P A 1
H10C H 0.454030 0.763426 0.833037 0.153 Uiso 0.5 1 calc GR . P A 1
C11 C 0.5734(5) 0.7218(8) 0.7639(4) 0.0758(14) Uani 0.5 1 d . . P A 2
H11A H 0.648184 0.669512 0.808099 0.114 Uiso 0.5 1 calc GR . P A 2
H11B H 0.525413 0.826979 0.793933 0.114 Uiso 0.5 1 calc GR . P A 2
H11C H 0.607191 0.782916 0.710839 0.114 Uiso 0.5 1 calc GR . P A 2
C12 C 0.4062(5) 0.4491(10) 0.7985(3) 0.0756(14) Uani 0.5 1 d . . P A 2
H12C H 0.469803 0.374633 0.843877 0.113 Uiso 0.5 1 calc GR . P A 2
H12B H 0.337228 0.353461 0.770037 0.113 Uiso 0.5 1 calc GR . P A 2
H12A H 0.364984 0.560605 0.829473 0.113 Uiso 0.5 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.369(3) . ?
O1 C2 1.437(2) . ?
O2 C1 1.210(3) . ?
O3 C3 1.327(2) . ?
O3 C5 1.491(2) . ?
C1 C4 1.447(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.486(3) . ?
C3 C4 1.318(3) . ?
C4 C8 1.495(3) . ?
C5 C6 1.606(5) . ?
C5 C7 1.550(5) . ?
C5 C9 1.364(6) . ?
C5 C10 1.589(6) . ?
C5 C11 1.581(5) . ?
C5 C12 1.390(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C8 1.606(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.597(5) . ?
C8 H8AA 0.9700 . ?
C8 H8AB 0.9700 . ?
C8 H8BC 0.9700 . ?
C8 H8BD 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12C 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12A 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
C1 O1 C2 109.08(15) . . ?
C3 O3 C5 114.80(15) . . ?
O1 C1 C4 109.29(18) . . ?
O2 C1 O1 120.2(2) . . ?
O2 C1 C4 130.5(2) . . ?
O1 C2 H2A 111.1 . . ?
O1 C2 H2B 111.1 . . ?
O1 C2 C3 103.10(16) . . ?
H2A C2 H2B 109.1 . . ?
C3 C2 H2A 111.1 . . ?
C3 C2 H2B 111.1 . . ?
O3 C3 C2 120.29(17) . . ?
C4 C3 O3 128.38(18) . . ?
C4 C3 C2 111.33(17) . . ?
C1 C4 C8 129.26(19) . . ?
C3 C4 C1 107.20(18) . . ?
C3 C4 C8 123.52(19) . . ?
O3 C5 C6 112.2(2) . . ?
O3 C5 C7 109.8(2) . . ?
O3 C5 C10 105.1(2) . . ?
O3 C5 C11 104.2(2) . . ?
C7 C5 C11 106.5(3) . . ?
C9 C5 O3 105.9(3) . . ?
C9 C5 C6 114.7(3) . . ?
C9 C5 C10 115.7(5) . . ?
C10 C5 C6 103.0(4) . . ?
C12 C5 O3 104.0(2) . . ?
C12 C5 C7 117.0(4) . . ?
C12 C5 C11 114.6(4) . . ?
C5 C6 H6A 110.6 . . ?
C5 C6 H6B 110.6 . . ?
C5 C6 C8 105.5(3) . . ?
H6A C6 H6B 108.8 . . ?
C8 C6 H6A 110.6 . . ?
C8 C6 H6B 110.6 . . ?
C5 C7 H7A 110.0 . . ?
C5 C7 H7B 110.0 . . ?
C5 C7 C8 108.6(3) . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 H7A 110.0 . . ?
C8 C7 H7B 110.0 . . ?
C4 C8 C6 104.5(2) . . ?
C4 C8 C7 102.9(2) . . ?
C4 C8 H8AA 110.8 . . ?
C4 C8 H8AB 110.8 . . ?
C4 C8 H8BC 111.2 . . ?
C4 C8 H8BD 111.2 . . ?
C6 C8 H8AA 110.8 . . ?
C6 C8 H8AB 110.8 . . ?
C7 C8 H8BC 111.2 . . ?
C7 C8 H8BD 111.2 . . ?
H8AA C8 H8AB 108.9 . . ?
H8BC C8 H8BD 109.1 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C12 H12C 109.5 . . ?
C5 C12 H12B 109.5 . . ?
C5 C12 H12A 109.5 . . ?
H12C C12 H12B 109.5 . . ?
H12C C12 H12A 109.5 . . ?
H12B C12 H12A 109.5 . . ?

_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 1.684
_oxdiff_exptl_absorpt_empirical_full_min 0.475
####################################################################### 
# 
# 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_nb2
_database_code_depnum_ccdc_archive 'CCDC 1954296'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;Spectropole de Marseille
France
;
_audit_update_record             
;
2019-09-17 deposited with the CCDC.	2020-03-12 downloaded from the CCDC.
;
_audit_creation_date             2017-03-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C14 H14 O3)'
_chemical_formula_sum            'C28 H28 O6'
_chemical_formula_weight         460.50
_chemical_melting_point          ?

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

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

_cell_length_a                   8.0723(3)
_cell_length_b                   17.1909(6)
_cell_length_c                   17.1065(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.515(4)
_cell_angle_gamma                90
_cell_volume                     2347.70(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8075
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.6660
_cell_measurement_theta_min      4.2780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74761
_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    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21406
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.613
_diffrn_reflns_theta_min         3.206
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     13.00  40.00   1.00   30.00    --    8.41  57.00 -30.00   27
  2  ω     53.00  80.00   1.00   30.00    --    8.41  57.00 -30.00   27
  3  ω    -13.00  31.00   1.00   30.00    --    8.41 -99.00 150.00   44
  4  ω     15.00  79.00   1.00   30.00    --    8.41  38.00-150.00   64
  5  ω    -20.00  78.00   1.00   30.00    --    8.41  57.00 -60.00   98
  6  ω    -46.00  45.00   1.00   30.00    --    8.41 -19.00-120.00   91
;
_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      0.0205004000
_diffrn_orient_matrix_UB_12      -0.0289071000
_diffrn_orient_matrix_UB_13      0.0294277000
_diffrn_orient_matrix_UB_21      -0.0671771000
_diffrn_orient_matrix_UB_22      0.0127119000
_diffrn_orient_matrix_UB_23      0.0192425000
_diffrn_orient_matrix_UB_31      -0.0544277000
_diffrn_orient_matrix_UB_32      -0.0265607000
_diffrn_orient_matrix_UB_33      -0.0228279000
_diffrn_oxdiff_ac3_digest_frames 
;
013a5cdaf640451c9d234087b9c0707bc6000271eb4
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01b469ea7f79ac1df283dde04a5b0d0a3eff3d
;
_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                3771
_reflns_number_total             5191
_reflns_odcompleteness_completeness 99.69
_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 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         0.148
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.074
_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)+(0.0487P)²+0.5446P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1263
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C24(H24A,H24B), C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C)
;
_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 0.88604(15) 0.84629(6) 0.37983(6) 0.0563(3) Uani 1 1 d . . . . .
O2 O 0.77622(18) 0.63196(7) 0.45994(9) 0.0742(4) Uani 1 1 d . . . . .
O3 O 1.01846(15) 0.88286(6) 0.49249(7) 0.0591(3) Uani 1 1 d . . . . .
C1 C 0.79136(19) 0.79512(10) 0.32991(9) 0.0501(4) Uani 1 1 d . . . . .
C2 C 0.7360(2) 0.82226(13) 0.25419(11) 0.0678(5) Uani 1 1 d . . . . .
H2 H 0.764481 0.871880 0.239092 0.081 Uiso 1 1 calc R . . . .
C3 C 0.6389(2) 0.77474(14) 0.20218(12) 0.0758(6) Uani 1 1 d . . . . .
H3 H 0.600032 0.792319 0.151353 0.091 Uiso 1 1 calc R . . . .
C4 C 0.5981(2) 0.70123(14) 0.22438(13) 0.0766(6) Uani 1 1 d . . . . .
H4 H 0.532362 0.669300 0.188407 0.092 Uiso 1 1 calc R . . . .
C5 C 0.6534(2) 0.67475(11) 0.29885(12) 0.0670(5) Uani 1 1 d . . . . .
H5 H 0.625582 0.624717 0.313017 0.080 Uiso 1 1 calc R . . . .
C6 C 0.75192(19) 0.72223(9) 0.35453(10) 0.0494(4) Uani 1 1 d . . . . .
C7 C 0.8087(2) 0.69736(9) 0.43623(10) 0.0524(4) Uani 1 1 d . . . . .
C8 C 0.9035(2) 0.75430(9) 0.48560(9) 0.0491(4) Uani 1 1 d . . . . .
C9 C 0.93487(19) 0.82411(9) 0.45542(9) 0.0462(4) Uani 1 1 d . . . . .
C10 C 0.9649(3) 0.73794(11) 0.57077(11) 0.0679(5) Uani 1 1 d . . . . .
H10A H 1.012051 0.685975 0.576094 0.082 Uiso 1 1 calc R . . . .
H10B H 0.871647 0.740097 0.600542 0.082 Uiso 1 1 calc R . . . .
C11 C 1.0970(3) 0.79674(11) 0.60412(11) 0.0696(5) Uani 1 1 d . . . . .
H11A H 1.114527 0.793267 0.661344 0.083 Uiso 1 1 calc R . . . .
H11B H 1.201966 0.784021 0.585899 0.083 Uiso 1 1 calc R . . . .
C12 C 1.0483(2) 0.87899(10) 0.57991(10) 0.0595(4) Uani 1 1 d . . . . .
C13 C 0.8898(3) 0.90651(14) 0.60801(14) 0.0861(6) Uani 1 1 d . . . . .
H13A H 0.867208 0.959230 0.591225 0.129 Uiso 1 1 calc GR . . . .
H13B H 0.903166 0.903936 0.664653 0.129 Uiso 1 1 calc GR . . . .
H13C H 0.798078 0.873877 0.586032 0.129 Uiso 1 1 calc GR . . . .
C14 C 1.1921(3) 0.93473(13) 0.60236(13) 0.0854(6) Uani 1 1 d . . . . .
H14A H 1.288325 0.916781 0.580658 0.128 Uiso 1 1 calc GR . . . .
H14B H 1.218476 0.937350 0.658894 0.128 Uiso 1 1 calc GR . . . .
H14C H 1.160955 0.985465 0.581802 0.128 Uiso 1 1 calc GR . . . .
O4 O 0.78388(14) 0.25786(6) 0.68809(6) 0.0528(3) Uani 1 1 d . . . . .
O5 O 0.50089(17) 0.20954(8) 0.47654(7) 0.0743(4) Uani 1 1 d . . . . .
O6 O 0.82953(15) 0.37635(6) 0.65709(7) 0.0570(3) Uani 1 1 d . . . . .
C15 C 0.71303(19) 0.18521(8) 0.67512(10) 0.0484(4) Uani 1 1 d . . . . .
C16 C 0.7463(2) 0.13240(10) 0.73639(12) 0.0651(5) Uani 1 1 d . . . . .
H16 H 0.813674 0.146091 0.783247 0.078 Uiso 1 1 calc R . . . .
C17 C 0.6781(2) 0.05974(11) 0.72667(14) 0.0756(6) Uani 1 1 d . . . . .
H17 H 0.699506 0.023572 0.767332 0.091 Uiso 1 1 calc R . . . .
C18 C 0.5778(2) 0.03931(11) 0.65734(15) 0.0766(6) Uani 1 1 d . . . . .
H18 H 0.531565 -0.010279 0.651605 0.092 Uiso 1 1 calc R . . . .
C19 C 0.5463(2) 0.09202(10) 0.59688(12) 0.0638(5) Uani 1 1 d . . . . .
H19 H 0.478909 0.077855 0.550172 0.077 Uiso 1 1 calc R . . . .
C20 C 0.61425(18) 0.16668(9) 0.60466(10) 0.0478(4) Uani 1 1 d . . . . .
C21 C 0.58505(19) 0.22488(10) 0.54093(10) 0.0506(4) Uani 1 1 d . . . . .
C22 C 0.66208(19) 0.29914(9) 0.55896(9) 0.0469(4) Uani 1 1 d . . . . .
C23 C 0.75309(18) 0.31141(8) 0.63044(9) 0.0446(3) Uani 1 1 d . . . . .
C24 C 0.6431(2) 0.36388(10) 0.49928(10) 0.0595(4) Uani 1 1 d . . . . .
H24A H 0.532600 0.386817 0.496407 0.071 Uiso 1 1 calc R . . . .
H24B H 0.654307 0.343280 0.447527 0.071 Uiso 1 1 calc R . . . .
C25 C 0.7759(2) 0.42583(10) 0.52242(10) 0.0624(5) Uani 1 1 d . . . . .
H25A H 0.882852 0.406896 0.510875 0.075 Uiso 1 1 calc R . . . .
H25B H 0.747232 0.471965 0.490643 0.075 Uiso 1 1 calc R . . . .
C26 C 0.7931(2) 0.44750(9) 0.60874(10) 0.0547(4) Uani 1 1 d . . . . .
C27 C 0.6349(3) 0.48268(11) 0.63118(13) 0.0728(5) Uani 1 1 d . . . . .
H27A H 0.541209 0.449772 0.612586 0.109 Uiso 1 1 calc GR . . . .
H27B H 0.617204 0.533226 0.607553 0.109 Uiso 1 1 calc GR . . . .
H27C H 0.645802 0.487367 0.687631 0.109 Uiso 1 1 calc GR . . . .
C28 C 0.9438(3) 0.49827(11) 0.63421(14) 0.0756(6) Uani 1 1 d . . . . .
H28A H 0.956753 0.506050 0.690361 0.113 Uiso 1 1 calc GR . . . .
H28B H 0.928425 0.547634 0.607901 0.113 Uiso 1 1 calc GR . . . .
H28C H 1.042167 0.473447 0.620594 0.113 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 C1 1.3761(19) . ?
O1 C9 1.3497(18) . ?
O2 C7 1.2365(19) . ?
O3 C9 1.3233(18) . ?
O3 C12 1.481(2) . ?
C1 C2 1.387(2) . ?
C1 C6 1.374(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.366(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.364(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.408(2) . ?
C6 C7 1.469(2) . ?
C7 C8 1.437(2) . ?
C8 C9 1.345(2) . ?
C8 C10 1.494(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.518(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.509(3) . ?
C12 C13 1.508(3) . ?
C12 C14 1.511(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O4 C15 1.3778(18) . ?
O4 C23 1.3450(17) . ?
O5 C21 1.2340(19) . ?
O6 C23 1.3235(18) . ?
O6 C26 1.4814(18) . ?
C15 C16 1.382(2) . ?
C15 C20 1.380(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.365(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.370(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.394(2) . ?
C20 C21 1.473(2) . ?
C21 C22 1.433(2) . ?
C22 C23 1.347(2) . ?
C22 C24 1.503(2) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.521(2) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.509(2) . ?
C26 C27 1.513(3) . ?
C26 C28 1.508(2) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
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
C9 O1 C1 118.07(12) . . ?
C9 O3 C12 116.41(12) . . ?
O1 C1 C2 115.92(16) . . ?
C6 C1 O1 121.68(14) . . ?
C6 C1 C2 122.38(16) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.8(2) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.52(19) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.44(18) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.81(19) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 117.05(16) . . ?
C1 C6 C7 120.21(14) . . ?
C5 C6 C7 122.73(16) . . ?
O2 C7 C6 121.69(16) . . ?
O2 C7 C8 123.15(16) . . ?
C8 C7 C6 115.15(14) . . ?
C7 C8 C10 121.03(15) . . ?
C9 C8 C7 119.74(15) . . ?
C9 C8 C10 119.22(15) . . ?
O3 C9 O1 107.42(12) . . ?
O3 C9 C8 127.49(14) . . ?
C8 C9 O1 125.09(14) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 C11 110.74(15) . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 C10 112.37(15) . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
O3 C12 C11 108.42(13) . . ?
O3 C12 C13 106.81(15) . . ?
O3 C12 C14 103.42(15) . . ?
C11 C12 C14 111.42(16) . . ?
C13 C12 C11 113.93(18) . . ?
C13 C12 C14 112.12(17) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C23 O4 C15 118.37(12) . . ?
C23 O6 C26 117.40(12) . . ?
O4 C15 C16 116.35(15) . . ?
O4 C15 C20 121.47(14) . . ?
C20 C15 C16 122.18(15) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 C15 118.62(18) . . ?
C17 C16 H16 120.7 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.84(18) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.04(17) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.67(17) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 117.65(15) . . ?
C15 C20 C21 119.87(14) . . ?
C19 C20 C21 122.48(15) . . ?
O5 C21 C20 121.48(15) . . ?
O5 C21 C22 123.12(15) . . ?
C22 C21 C20 115.40(13) . . ?
C21 C22 C24 121.07(14) . . ?
C23 C22 C21 119.72(14) . . ?
C23 C22 C24 119.21(14) . . ?
O4 C23 C22 125.12(14) . . ?
O6 C23 O4 107.38(12) . . ?
O6 C23 C22 127.50(14) . . ?
C22 C24 H24A 109.6 . . ?
C22 C24 H24B 109.6 . . ?
C22 C24 C25 110.16(14) . . ?
H24A C24 H24B 108.1 . . ?
C25 C24 H24A 109.6 . . ?
C25 C24 H24B 109.6 . . ?
C24 C25 H25A 109.0 . . ?
C24 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
C26 C25 C24 112.75(14) . . ?
C26 C25 H25A 109.0 . . ?
C26 C25 H25B 109.0 . . ?
O6 C26 C25 108.93(13) . . ?
O6 C26 C27 107.07(14) . . ?
O6 C26 C28 103.39(13) . . ?
C25 C26 C27 112.83(15) . . ?
C28 C26 C25 112.27(16) . . ?
C28 C26 C27 111.74(16) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

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 -178.84(16) . . . . ?
O1 C1 C6 C5 179.55(14) . . . . ?
O1 C1 C6 C7 0.9(2) . . . . ?
O2 C7 C8 C9 179.56(16) . . . . ?
O2 C7 C8 C10 -1.8(3) . . . . ?
C1 O1 C9 O3 -177.92(13) . . . . ?
C1 O1 C9 C8 2.6(2) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C1 C6 C7 O2 -179.50(16) . . . . ?
C1 C6 C7 C8 0.6(2) . . . . ?
C2 C1 C6 C5 0.8(2) . . . . ?
C2 C1 C6 C7 -177.81(16) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C4 C5 C6 C7 177.56(16) . . . . ?
C5 C6 C7 O2 1.9(3) . . . . ?
C5 C6 C7 C8 -177.99(15) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
C6 C7 C8 C9 -0.5(2) . . . . ?
C6 C7 C8 C10 178.09(15) . . . . ?
C7 C8 C9 O1 -1.1(2) . . . . ?
C7 C8 C9 O3 179.52(15) . . . . ?
C7 C8 C10 C11 165.28(16) . . . . ?
C8 C10 C11 C12 44.8(2) . . . . ?
C9 O1 C1 C2 176.36(15) . . . . ?
C9 O1 C1 C6 -2.4(2) . . . . ?
C9 O3 C12 C11 42.1(2) . . . . ?
C9 O3 C12 C13 -81.08(18) . . . . ?
C9 O3 C12 C14 160.46(15) . . . . ?
C9 C8 C10 C11 -16.1(2) . . . . ?
C10 C8 C9 O1 -179.73(16) . . . . ?
C10 C8 C9 O3 0.9(3) . . . . ?
C10 C11 C12 O3 -57.6(2) . . . . ?
C10 C11 C12 C13 61.2(2) . . . . ?
C10 C11 C12 C14 -170.78(17) . . . . ?
C12 O3 C9 O1 165.65(13) . . . . ?
C12 O3 C9 C8 -14.9(2) . . . . ?
O4 C15 C16 C17 179.58(17) . . . . ?
O4 C15 C20 C19 -179.41(14) . . . . ?
O4 C15 C20 C21 1.0(2) . . . . ?
O5 C21 C22 C23 -179.58(16) . . . . ?
O5 C21 C22 C24 0.4(3) . . . . ?
C15 O4 C23 O6 178.25(13) . . . . ?
C15 O4 C23 C22 -2.4(2) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C15 C20 C21 O5 178.15(15) . . . . ?
C15 C20 C21 C22 -1.3(2) . . . . ?
C16 C15 C20 C19 0.5(2) . . . . ?
C16 C15 C20 C21 -179.09(16) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C18 C19 C20 C15 -0.2(3) . . . . ?
C18 C19 C20 C21 179.36(17) . . . . ?
C19 C20 C21 O5 -1.4(3) . . . . ?
C19 C20 C21 C22 179.17(15) . . . . ?
C20 C15 C16 C17 -0.3(3) . . . . ?
C20 C21 C22 C23 -0.2(2) . . . . ?
C20 C21 C22 C24 179.80(14) . . . . ?
C21 C22 C23 O4 2.1(2) . . . . ?
C21 C22 C23 O6 -178.70(15) . . . . ?
C21 C22 C24 C25 -162.80(15) . . . . ?
C22 C24 C25 C26 -46.1(2) . . . . ?
C23 O4 C15 C16 -179.16(15) . . . . ?
C23 O4 C15 C20 0.8(2) . . . . ?
C23 O6 C26 C25 -37.61(19) . . . . ?
C23 O6 C26 C27 84.69(18) . . . . ?
C23 O6 C26 C28 -157.19(15) . . . . ?
C23 C22 C24 C25 17.2(2) . . . . ?
C24 C22 C23 O4 -177.90(15) . . . . ?
C24 C22 C23 O6 1.3(3) . . . . ?
C24 C25 C26 O6 56.28(19) . . . . ?
C24 C25 C26 C27 -62.47(19) . . . . ?
C24 C25 C26 C28 170.18(15) . . . . ?
C26 O6 C23 O4 -171.00(13) . . . . ?
C26 O6 C23 C22 9.7(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 1.355
_oxdiff_exptl_absorpt_empirical_full_min 0.692
####################################################################### 
# 
# 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_nb1
_database_code_depnum_ccdc_archive 'CCDC 1954294'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;Spectropole de Marseille
France
;
_audit_update_record             
;
2019-09-17 deposited with the CCDC.	2020-03-12 downloaded from the CCDC.
;
_audit_creation_date             2017-03-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C14 H14 O3)'
_chemical_formula_sum            'C28 H28 O6'
_chemical_formula_weight         460.50
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c14 h14 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                   9.8069(4)
_cell_length_b                   10.0568(5)
_cell_length_c                   12.7810(6)
_cell_angle_alpha                86.854(4)
_cell_angle_beta                 70.545(4)
_cell_angle_gamma                87.679(4)
_cell_volume                     1186.45(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7165
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.4780
_cell_measurement_theta_min      4.0300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84132
_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    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.815
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17392
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.815
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.977
_diffrn_reflns_theta_min         3.371
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.815
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  32.00   1.00   15.00    --   -7.78 -99.00 -60.00   46
  2  ω    -85.00 -58.00   1.00   15.00    --   -7.78 156.00 109.75   27
  3  ω      7.00  85.00   1.00   15.00    --    8.41  77.00-150.00   78
  4  ω     21.00  49.00   1.00   15.00    --    8.41 -99.00 150.00   28
  5  ω    -15.00  83.00   1.00   15.00    --    8.41  38.00 150.00   98
  6  ω    -20.00  49.00   1.00   15.00    --    8.41 -99.00  60.00   69
  7  ω    -72.00  73.00   1.00   15.00    --    8.41   0.00  90.00  145
  8  ω    -15.00  53.00   1.00   15.00    --   10.00-102.00 -31.91   68
;
_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      -0.0113091000
_diffrn_orient_matrix_UB_12      0.0684977000
_diffrn_orient_matrix_UB_13      0.0116562000
_diffrn_orient_matrix_UB_21      0.0747631000
_diffrn_orient_matrix_UB_22      0.0109855000
_diffrn_orient_matrix_UB_23      -0.0271653000
_diffrn_orient_matrix_UB_31      -0.0130254000
_diffrn_orient_matrix_UB_32      0.0134007000
_diffrn_orient_matrix_UB_33      -0.0509611000
_diffrn_oxdiff_ac3_digest_frames 
;
0109df002d98cd7eec2804822bf76a8d090002721bf
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01a87a70f22eebf8c8dd89f82cf913f4884d1b
;
_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                3825
_reflns_number_total             5143
_reflns_odcompleteness_completeness 99.73
_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 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         0.181
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         5143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.031
_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)+(0.0496P)²+0.3257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1277
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H24B(0.5) H24A(0.5) H24D(0.5) H24C(0.5) C25(0.5) H25A(0.5)
 H25B(0.5) C26(0.5) H26A(0.5) H26B(0.5) C28(0.5) H28A(0.5) H28B(0.5) H28C(0.5)
 C29(0.5) H29A(0.5) H29B(0.5) H29C(0.5) C30(0.5) H30A(0.5) H30B(0.5) H30C(0.5)
 C31(0.5) H31A(0.5) H31B(0.5) H31C(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C24(H24B,H24A), C24(H24D,H24C), C25(H25A,H25B), C26(H26A,H26B), C9(H9A,H9B),
 C10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C18(H18), C19(H19), C2(H2), C3(H3), C4(H4), C5(H5)
3.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,
 H31C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_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
O4 O 0.37248(13) 1.07437(11) 0.71643(10) 0.0555(3) Uani 1 1 d . . . . .
O5 O 0.36295(17) 0.93892(14) 0.85906(11) 0.0751(4) Uani 1 1 d . . . . .
O6 O 0.18935(15) 0.80187(11) 0.57966(10) 0.0617(3) Uani 1 1 d . . . . .
C15 C 0.29766(16) 1.00815(14) 0.56657(13) 0.0428(3) Uani 1 1 d . . . . .
C16 C 0.28671(19) 1.04019(17) 0.46201(14) 0.0543(4) Uani 1 1 d . . . . .
H16 H 0.247256 0.979785 0.428194 0.065 Uiso 1 1 calc R . . . .
C17 C 0.3339(2) 1.16050(18) 0.40879(16) 0.0623(5) Uani 1 1 d . . . . .
H17 H 0.327581 1.180828 0.338660 0.075 Uiso 1 1 calc R . . . .
C18 C 0.39068(19) 1.25122(18) 0.45923(17) 0.0631(5) Uani 1 1 d . . . . .
H18 H 0.421125 1.333012 0.423144 0.076 Uiso 1 1 calc R . . . .
C19 C 0.40276(18) 1.22233(17) 0.56179(17) 0.0582(4) Uani 1 1 d . . . . .
H19 H 0.441047 1.283756 0.595557 0.070 Uiso 1 1 calc R . . . .
C20 C 0.35698(16) 1.10006(15) 0.61434(13) 0.0455(4) Uani 1 1 d . . . . .
C21 C 0.33553(19) 0.95389(17) 0.77355(14) 0.0518(4) Uani 1 1 d . . . . .
C22 C 0.26720(17) 0.85828(15) 0.72887(13) 0.0470(4) Uani 1 1 d . . . . .
C23 C 0.24994(16) 0.88472(14) 0.62928(13) 0.0429(3) Uani 1 1 d . . . . .
C24 C 0.2204(2) 0.73010(18) 0.79405(16) 0.0648(5) Uani 1 1 d . . . . .
H24B H 0.126292 0.741910 0.850238 0.078 Uiso 0.5 1 calc R . P A 1
H24A H 0.289216 0.700461 0.830612 0.078 Uiso 0.5 1 calc R . P A 1
H24D H 0.193965 0.744487 0.872822 0.078 Uiso 0.5 1 calc R . P B 2
H24C H 0.299529 0.664989 0.774334 0.078 Uiso 0.5 1 calc R . P B 2
C25 C 0.2132(4) 0.6268(3) 0.7112(3) 0.0505(8) Uani 0.5 1 d . . P C 1
H25A H 0.310657 0.603238 0.664796 0.061 Uiso 0.5 1 calc R . P C 1
H25B H 0.169141 0.546660 0.752155 0.061 Uiso 0.5 1 calc R . P C 1
C26 C 0.0891(5) 0.6773(4) 0.7685(4) 0.0798(12) Uani 0.5 1 d . . P C 2
H26A H 0.004481 0.733983 0.800184 0.096 Uiso 0.5 1 calc R . P C 2
H26B H 0.067804 0.587710 0.800552 0.096 Uiso 0.5 1 calc R . P C 2
C27 C 0.12852(19) 0.67736(17) 0.63889(15) 0.0560(4) Uani 1 1 d . . . . .
C28 C -0.0211(4) 0.7245(6) 0.6992(4) 0.0862(14) Uani 0.5 1 d . . P C 1
H28A H -0.018842 0.789525 0.750777 0.129 Uiso 0.5 1 calc GR . P C 1
H28B H -0.077559 0.650509 0.738742 0.129 Uiso 0.5 1 calc GR . P C 1
H28C H -0.063791 0.764006 0.646943 0.129 Uiso 0.5 1 calc GR . P C 1
C29 C -0.0107(6) 0.6468(6) 0.6170(6) 0.1035(18) Uani 0.5 1 d . . P C 2
H29A H -0.082532 0.714797 0.647212 0.155 Uiso 0.5 1 calc GR . P C 2
H29B H -0.045270 0.561977 0.651691 0.155 Uiso 0.5 1 calc GR . P C 2
H29C H 0.008359 0.644548 0.538442 0.155 Uiso 0.5 1 calc GR . P C 2
C30 C 0.1424(7) 0.5849(4) 0.5439(4) 0.0867(15) Uani 0.5 1 d . . P C 1
H30A H 0.085954 0.621143 0.500077 0.130 Uiso 0.5 1 calc GR . P C 1
H30B H 0.107919 0.498390 0.574350 0.130 Uiso 0.5 1 calc GR . P C 1
H30C H 0.242042 0.577389 0.498037 0.130 Uiso 0.5 1 calc GR . P C 1
C31 C 0.2432(5) 0.5746(4) 0.5909(4) 0.0853(13) Uani 0.5 1 d . . P C 2
H31A H 0.268185 0.578287 0.511554 0.128 Uiso 0.5 1 calc GR . P C 2
H31B H 0.207930 0.487900 0.620047 0.128 Uiso 0.5 1 calc GR . P C 2
H31C H 0.327220 0.591521 0.610312 0.128 Uiso 0.5 1 calc GR . P C 2
O1 O 0.56510(13) 0.58474(11) 0.81708(10) 0.0561(3) Uani 1 1 d . . . . .
O2 O 0.51269(16) 0.45248(13) 0.70557(12) 0.0724(4) Uani 1 1 d . . . . .
O3 O 0.83368(12) 0.29966(10) 0.89373(9) 0.0502(3) Uani 1 1 d . . . . .
C1 C 0.72329(16) 0.51287(14) 0.91940(12) 0.0425(3) Uani 1 1 d . . . . .
C2 C 0.7901(2) 0.54444(18) 0.99533(14) 0.0599(5) Uani 1 1 d . . . . .
H2 H 0.851218 0.482354 1.014994 0.072 Uiso 1 1 calc R . . . .
C3 C 0.7656(3) 0.6672(2) 1.04098(17) 0.0758(6) Uani 1 1 d . . . . .
H3 H 0.809259 0.687327 1.092395 0.091 Uiso 1 1 calc R . . . .
C4 C 0.6770(3) 0.7610(2) 1.01140(17) 0.0741(6) Uani 1 1 d . . . . .
H4 H 0.662299 0.844108 1.042372 0.089 Uiso 1 1 calc R . . . .
C5 C 0.6105(2) 0.73289(17) 0.93704(15) 0.0623(5) Uani 1 1 d . . . . .
H5 H 0.550843 0.796191 0.917002 0.075 Uiso 1 1 calc R . . . .
C6 C 0.63351(17) 0.60841(15) 0.89198(13) 0.0464(4) Uani 1 1 d . . . . .
C7 C 0.57759(18) 0.46287(16) 0.76993(14) 0.0498(4) Uani 1 1 d . . . . .
C8 C 0.66682(16) 0.36042(14) 0.79910(12) 0.0427(3) Uani 1 1 d . . . . .
C9 C 0.6721(2) 0.22612(16) 0.75244(15) 0.0554(4) Uani 1 1 d . . . . .
H9A H 0.728113 0.229777 0.673917 0.067 Uiso 1 1 calc R . . . .
H9B H 0.574937 0.199365 0.760821 0.067 Uiso 1 1 calc R . . . .
C10 C 0.7413(2) 0.12558(16) 0.81406(15) 0.0563(4) Uani 1 1 d . . . . .
H10A H 0.671870 0.103077 0.886482 0.068 Uiso 1 1 calc R . . . .
H10B H 0.766731 0.044749 0.773069 0.068 Uiso 1 1 calc R . . . .
C11 C 0.87554(19) 0.17951(16) 0.82856(14) 0.0523(4) Uani 1 1 d . . . . .
C12 C 0.74094(16) 0.38607(14) 0.86717(12) 0.0396(3) Uani 1 1 d . . . . .
C13 C 0.9900(2) 0.2202(2) 0.71960(18) 0.0784(6) Uani 1 1 d . . . . .
H13A H 0.952393 0.291404 0.683200 0.118 Uiso 1 1 calc GR . . . .
H13B H 1.016226 0.145383 0.672780 0.118 Uiso 1 1 calc GR . . . .
H13C H 1.073830 0.249562 0.733854 0.118 Uiso 1 1 calc GR . . . .
C14 C 0.9372(2) 0.08490(19) 0.89863(19) 0.0729(6) Uani 1 1 d . . . . .
H14A H 1.014338 0.126957 0.913758 0.109 Uiso 1 1 calc GR . . . .
H14B H 0.973639 0.005420 0.859215 0.109 Uiso 1 1 calc GR . . . .
H14C H 0.862558 0.062324 0.967345 0.109 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
O4 C20 1.3727(19) . ?
O4 C21 1.376(2) . ?
O5 C21 1.2098(19) . ?
O6 C23 1.3411(18) . ?
O6 C27 1.467(2) . ?
C15 C16 1.395(2) . ?
C15 C20 1.381(2) . ?
C15 C23 1.446(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.373(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.370(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.385(2) . ?
C21 C22 1.438(2) . ?
C22 C23 1.350(2) . ?
C22 C24 1.497(2) . ?
C24 H24B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24D 0.9700 . ?
C24 H24C 0.9700 . ?
C24 C25 1.544(4) . ?
C24 C26 1.550(5) . ?
C27 C28 1.484(5) . ?
C27 C29 1.527(5) . ?
C27 C30 1.536(4) . ?
C27 C31 1.491(5) . ?
O1 C6 1.3744(19) . ?
O1 C7 1.3784(19) . ?
O2 C7 1.2067(19) . ?
O3 C11 1.4713(19) . ?
O3 C12 1.3442(17) . ?
C1 C2 1.395(2) . ?
C1 C6 1.386(2) . ?
C1 C12 1.449(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.373(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.366(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(2) . ?
C7 C8 1.438(2) . ?
C8 C9 1.498(2) . ?
C8 C12 1.346(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.522(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.515(2) . ?
C11 C13 1.517(3) . ?
C11 C14 1.514(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C20 O4 C21 121.57(12) . . ?
C23 O6 C27 118.97(12) . . ?
C16 C15 C23 124.30(14) . . ?
C20 C15 C16 118.33(15) . . ?
C20 C15 C23 117.36(14) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.33(16) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.08(18) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.81(17) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 120.6 . . ?
C18 C19 C20 118.85(16) . . ?
C20 C19 H19 120.6 . . ?
O4 C20 C15 121.38(14) . . ?
O4 C20 C19 117.04(14) . . ?
C15 C20 C19 121.58(16) . . ?
O4 C21 C22 118.47(14) . . ?
O5 C21 O4 115.87(15) . . ?
O5 C21 C22 125.66(17) . . ?
C21 C22 C24 118.34(14) . . ?
C23 C22 C21 119.62(15) . . ?
C23 C22 C24 122.02(15) . . ?
O6 C23 C15 114.25(13) . . ?
O6 C23 C22 124.38(14) . . ?
C22 C23 C15 121.37(14) . . ?
C22 C24 H24B 110.3 . . ?
C22 C24 H24A 110.3 . . ?
C22 C24 H24D 109.8 . . ?
C22 C24 H24C 109.8 . . ?
C22 C24 C25 107.17(17) . . ?
C22 C24 C26 109.4(2) . . ?
O6 C27 C25 110.11(17) . . ?
O6 C27 C26 114.7(2) . . ?
O6 C27 C28 99.8(2) . . ?
O6 C27 C29 110.4(2) . . ?
O6 C27 C30 102.8(2) . . ?
O6 C27 C31 104.1(2) . . ?
C6 O1 C7 121.38(12) . . ?
C12 O3 C11 116.84(11) . . ?
C2 C1 C12 124.33(15) . . ?
C6 C1 C2 118.20(15) . . ?
C6 C1 C12 117.47(13) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.95(18) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.68(18) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.59(17) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.83(18) . . ?
C6 C5 H5 120.6 . . ?
O1 C6 C1 121.42(13) . . ?
O1 C6 C5 116.84(15) . . ?
C5 C6 C1 121.73(16) . . ?
O1 C7 C8 118.48(13) . . ?
O2 C7 O1 116.03(14) . . ?
O2 C7 C8 125.49(15) . . ?
C7 C8 C9 117.74(13) . . ?
C12 C8 C7 120.18(14) . . ?
C12 C8 C9 122.08(13) . . ?
C8 C9 H9A 109.9 . . ?
C8 C9 H9B 109.9 . . ?
C8 C9 C10 109.08(13) . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 H9A 109.9 . . ?
C10 C9 H9B 109.9 . . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 C9 111.71(14) . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
O3 C11 C10 108.35(13) . . ?
O3 C11 C13 106.94(14) . . ?
O3 C11 C14 104.17(13) . . ?
C10 C11 C13 113.33(16) . . ?
C14 C11 C10 111.90(15) . . ?
C14 C11 C13 111.56(16) . . ?
O3 C12 C1 114.62(13) . . ?
O3 C12 C8 124.51(13) . . ?
C8 C12 C1 120.87(13) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
O4 C21 C22 C23 4.5(2) . . . . ?
O4 C21 C22 C24 -176.99(15) . . . . ?
O5 C21 C22 C23 -176.38(17) . . . . ?
O5 C21 C22 C24 2.2(3) . . . . ?
C15 C16 C17 C18 -0.9(3) . . . . ?
C16 C15 C20 O4 -179.25(14) . . . . ?
C16 C15 C20 C19 1.1(2) . . . . ?
C16 C15 C23 O6 -1.6(2) . . . . ?
C16 C15 C23 C22 178.18(15) . . . . ?
C16 C17 C18 C19 0.9(3) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C18 C19 C20 O4 179.26(14) . . . . ?
C18 C19 C20 C15 -1.0(2) . . . . ?
C20 O4 C21 O5 175.11(14) . . . . ?
C20 O4 C21 C22 -5.6(2) . . . . ?
C20 C15 C16 C17 -0.1(2) . . . . ?
C20 C15 C23 O6 178.00(13) . . . . ?
C20 C15 C23 C22 -2.2(2) . . . . ?
C21 O4 C20 C15 2.9(2) . . . . ?
C21 O4 C20 C19 -177.45(14) . . . . ?
C21 C22 C23 O6 179.17(14) . . . . ?
C21 C22 C23 C15 -0.6(2) . . . . ?
C23 C15 C16 C17 179.47(15) . . . . ?
C23 C15 C20 O4 1.2(2) . . . . ?
C23 C15 C20 C19 -178.52(14) . . . . ?
C24 C22 C23 O6 0.7(3) . . . . ?
C24 C22 C23 C15 -179.06(15) . . . . ?
C27 O6 C23 C15 -176.12(13) . . . . ?
C27 O6 C23 C22 4.1(2) . . . . ?
O1 C7 C8 C9 176.40(15) . . . . ?
O1 C7 C8 C12 -2.9(2) . . . . ?
O2 C7 C8 C9 -4.6(3) . . . . ?
O2 C7 C8 C12 176.10(17) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C2 C1 C6 O1 179.42(14) . . . . ?
C2 C1 C6 C5 0.6(2) . . . . ?
C2 C1 C12 O3 -2.8(2) . . . . ?
C2 C1 C12 C8 176.46(15) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 O1 -179.67(16) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C6 O1 C7 O2 179.71(15) . . . . ?
C6 O1 C7 C8 -1.2(2) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
C6 C1 C12 O3 177.48(13) . . . . ?
C6 C1 C12 C8 -3.3(2) . . . . ?
C7 O1 C6 C1 3.0(2) . . . . ?
C7 O1 C6 C5 -178.11(15) . . . . ?
C7 C8 C9 C10 -166.56(15) . . . . ?
C7 C8 C12 O3 -175.76(14) . . . . ?
C7 C8 C12 C1 5.1(2) . . . . ?
C8 C9 C10 C11 -44.9(2) . . . . ?
C9 C8 C12 O3 5.0(2) . . . . ?
C9 C8 C12 C1 -174.12(14) . . . . ?
C9 C10 C11 O3 60.63(18) . . . . ?
C9 C10 C11 C13 -57.88(19) . . . . ?
C9 C10 C11 C14 174.91(15) . . . . ?
C11 O3 C12 C1 -169.46(12) . . . . ?
C11 O3 C12 C8 11.4(2) . . . . ?
C12 O3 C11 C10 -43.12(18) . . . . ?
C12 O3 C11 C13 79.37(17) . . . . ?
C12 O3 C11 C14 -162.39(14) . . . . ?
C12 C1 C2 C3 -179.50(17) . . . . ?
C12 C1 C6 O1 -0.8(2) . . . . ?
C12 C1 C6 C5 -179.61(14) . . . . ?
C12 C8 C9 C10 12.7(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 1.323
_oxdiff_exptl_absorpt_empirical_full_min 0.742
