# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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 
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data_sa3597
_database_code_depnum_ccdc_archive 'CCDC 1037207'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-02-04 downloaded from the CCDC.
;
_audit_creation_date             2014-09-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H22 O2'
_chemical_formula_sum            'C22 H22 O2'
_chemical_formula_weight         318.39
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.935(3)
_cell_length_b                   12.812(3)
_cell_length_c                   20.795(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3179.6(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8007
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4813
_cell_measurement_theta_min      1.8670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11691
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         3.180
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             4076
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0109
_diffrn_orient_matrix_UB_12      -0.0765
_diffrn_orient_matrix_UB_13      -0.0324
_diffrn_orient_matrix_UB_21      -0.0697
_diffrn_orient_matrix_UB_22      0.0217
_diffrn_orient_matrix_UB_23      -0.0277
_diffrn_orient_matrix_UB_31      0.0208
_diffrn_orient_matrix_UB_32      0.0144
_diffrn_orient_matrix_UB_33      -0.0409
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3306
_reflns_number_total             3627
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution    
;
'SHELXS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.255
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3627
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0744
_refine_ls_restrained_S_all      1.255
_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)+(0.0215P)²+2.7588P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1343
_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:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C15(H15), C16(H16), C18(H18)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.22256(13) 0.40667(13) 0.32032(7) 0.0333(4) Uani 1 1 d . . . . .
O2 O 0.82513(14) 0.00546(15) 0.44059(8) 0.0408(4) Uani 1 1 d . . . . .
C1 C 0.28620(18) 0.35799(17) 0.27403(10) 0.0261(5) Uani 1 1 d . . . . .
C2 C 0.2668(2) 0.36309(17) 0.20767(10) 0.0299(5) Uani 1 1 d . . . . .
H2 H 0.2068 0.4020 0.1921 0.036 Uiso 1 1 calc R . . . .
C3 C 0.3366(2) 0.31034(18) 0.16480(10) 0.0309(5) Uani 1 1 d . . . . .
H3 H 0.3222 0.3153 0.1210 0.037 Uiso 1 1 calc R . . . .
C4 C 0.42649(19) 0.25090(17) 0.18540(10) 0.0262(5) Uani 1 1 d . . . . .
C5 C 0.5087(2) 0.19147(19) 0.14394(11) 0.0344(6) Uani 1 1 d . . . . .
H5A H 0.5699 0.2372 0.1319 0.041 Uiso 1 1 calc R . . . .
H5B H 0.4715 0.1688 0.1049 0.041 Uiso 1 1 calc R . . . .
C6 C 0.5554(2) 0.09600(18) 0.17958(10) 0.0320(5) Uani 1 1 d . . . . .
H6A H 0.6116 0.0629 0.1528 0.038 Uiso 1 1 calc R . . . .
H6B H 0.4953 0.0462 0.1861 0.038 Uiso 1 1 calc R . . . .
C7 C 0.60813(19) 0.12239(17) 0.24530(10) 0.0286(5) Uani 1 1 d . . . . .
H7A H 0.6242 0.0582 0.2683 0.034 Uiso 1 1 calc R . . . .
H7B H 0.6783 0.1590 0.2386 0.034 Uiso 1 1 calc R . . . .
C8 C 0.53113(18) 0.18913(16) 0.28510(10) 0.0245(4) Uani 1 1 d . . . . .
C9 C 0.44374(18) 0.24740(16) 0.25176(10) 0.0245(4) Uani 1 1 d . . . . .
C10 C 0.37550(19) 0.29903(16) 0.29588(10) 0.0245(5) Uani 1 1 d . . . . .
C11 C 0.42125(18) 0.27881(16) 0.36233(10) 0.0249(5) Uani 1 1 d . . . . .
H11 H 0.4500 0.3445 0.3800 0.030 Uiso 1 1 calc R . . . .
C12 C 0.34333(19) 0.22893(18) 0.41152(10) 0.0278(5) Uani 1 1 d . . . . .
H12A H 0.3169 0.1620 0.3958 0.033 Uiso 1 1 calc R . . . .
H12B H 0.2789 0.2735 0.4188 0.033 Uiso 1 1 calc R . . . .
C13 C 0.40848(19) 0.21405(18) 0.47416(10) 0.0281(5) Uani 1 1 d . . . . .
H13A H 0.4211 0.2818 0.4937 0.034 Uiso 1 1 calc R . . . .
H13B H 0.3633 0.1733 0.5037 0.034 Uiso 1 1 calc R . . . .
C14 C 0.52028(18) 0.16015(16) 0.46500(9) 0.0236(4) Uani 1 1 d . . . . .
C15 C 0.57061(19) 0.11029(17) 0.51674(10) 0.0280(5) Uani 1 1 d . . . . .
H15 H 0.5350 0.1120 0.5565 0.034 Uiso 1 1 calc R . . . .
C16 C 0.67199(19) 0.05808(18) 0.51137(10) 0.0289(5) Uani 1 1 d . . . . .
H16 H 0.7040 0.0256 0.5469 0.035 Uiso 1 1 calc R . . . .
C17 C 0.72449(18) 0.05542(18) 0.45197(11) 0.0285(5) Uani 1 1 d . . . . .
C18 C 0.67737(19) 0.10544(18) 0.39948(10) 0.0287(5) Uani 1 1 d . . . . .
H18 H 0.7145 0.1045 0.3602 0.034 Uiso 1 1 calc R . . . .
C19 C 0.57480(18) 0.15725(16) 0.40472(10) 0.0236(4) Uani 1 1 d . . . . .
C20 C 0.51955(18) 0.20612(16) 0.34941(10) 0.0235(4) Uani 1 1 d . . . . .
C21 C 0.1294(2) 0.46732(18) 0.29919(12) 0.0348(5) Uani 1 1 d . . . . .
H21A H 0.0795 0.4241 0.2746 0.052 Uiso 1 1 calc GR . . . .
H21B H 0.1555 0.5239 0.2729 0.052 Uiso 1 1 calc GR . . . .
H21C H 0.0904 0.4948 0.3358 0.052 Uiso 1 1 calc GR . . . .
C22 C 0.8682(2) -0.0588(2) 0.49012(14) 0.0487(7) Uani 1 1 d . . . . .
H22A H 0.9350 -0.0930 0.4753 0.073 Uiso 1 1 calc GR . . . .
H22B H 0.8133 -0.1103 0.5016 0.073 Uiso 1 1 calc GR . . . .
H22C H 0.8855 -0.0168 0.5270 0.073 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 1.376(3) . ?
O1 C21 1.426(3) . ?
O2 C17 1.381(3) . ?
O2 C22 1.416(3) . ?
C1 C2 1.401(3) . ?
C1 C10 1.383(3) . ?
C2 C3 1.395(3) . ?
C3 C4 1.384(3) . ?
C4 C5 1.512(3) . ?
C4 C9 1.396(3) . ?
C5 C6 1.535(3) . ?
C6 C7 1.542(3) . ?
C7 C8 1.504(3) . ?
C8 C9 1.458(3) . ?
C8 C20 1.362(3) . ?
C9 C10 1.394(3) . ?
C10 C11 1.508(3) . ?
C11 C12 1.523(3) . ?
C11 C20 1.522(3) . ?
C12 C13 1.529(3) . ?
C13 C14 1.514(3) . ?
C14 C15 1.388(3) . ?
C14 C19 1.413(3) . ?
C15 C16 1.387(3) . ?
C16 C17 1.386(3) . ?
C17 C18 1.385(3) . ?
C18 C19 1.397(3) . ?
C19 C20 1.466(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C21 117.52(17) . . ?
C17 O2 C22 117.44(19) . . ?
O1 C1 C2 125.2(2) . . ?
O1 C1 C10 116.31(18) . . ?
C10 C1 C2 118.5(2) . . ?
C3 C2 C1 120.5(2) . . ?
C4 C3 C2 122.1(2) . . ?
C3 C4 C5 127.1(2) . . ?
C3 C4 C9 116.0(2) . . ?
C9 C4 C5 116.9(2) . . ?
C4 C5 C6 111.20(18) . . ?
C5 C6 C7 113.68(19) . . ?
C8 C7 C6 111.30(19) . . ?
C9 C8 C7 117.81(19) . . ?
C20 C8 C7 133.9(2) . . ?
C20 C8 C9 108.21(19) . . ?
C4 C9 C8 126.3(2) . . ?
C10 C9 C4 123.3(2) . . ?
C10 C9 C8 110.36(18) . . ?
C1 C10 C9 119.55(19) . . ?
C1 C10 C11 132.4(2) . . ?
C9 C10 C11 108.06(18) . . ?
C10 C11 C12 117.80(18) . . ?
C10 C11 C20 102.86(17) . . ?
C20 C11 C12 109.42(17) . . ?
C11 C12 C13 108.31(18) . . ?
C14 C13 C12 113.43(17) . . ?
C15 C14 C13 119.58(19) . . ?
C15 C14 C19 118.4(2) . . ?
C19 C14 C13 121.96(18) . . ?
C16 C15 C14 122.5(2) . . ?
C17 C16 C15 118.6(2) . . ?
O2 C17 C16 123.9(2) . . ?
O2 C17 C18 115.6(2) . . ?
C18 C17 C16 120.5(2) . . ?
C17 C18 C19 120.9(2) . . ?
C14 C19 C20 118.53(19) . . ?
C18 C19 C14 119.03(19) . . ?
C18 C19 C20 122.40(19) . . ?
C8 C20 C11 110.45(18) . . ?
C8 C20 C19 131.0(2) . . ?
C19 C20 C11 118.01(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -179.9(2) . . . . ?
O1 C1 C10 C9 179.99(19) . . . . ?
O1 C1 C10 C11 -2.1(4) . . . . ?
O2 C17 C18 C19 179.0(2) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C1 C10 C11 C12 59.2(3) . . . . ?
C1 C10 C11 C20 179.6(2) . . . . ?
C2 C1 C10 C9 0.5(3) . . . . ?
C2 C1 C10 C11 178.4(2) . . . . ?
C2 C3 C4 C5 -179.2(2) . . . . ?
C2 C3 C4 C9 -0.4(3) . . . . ?
C3 C4 C5 C6 -151.2(2) . . . . ?
C3 C4 C9 C8 178.9(2) . . . . ?
C3 C4 C9 C10 0.5(3) . . . . ?
C4 C5 C6 C7 -54.4(3) . . . . ?
C4 C9 C10 C1 -0.6(3) . . . . ?
C4 C9 C10 C11 -178.94(19) . . . . ?
C5 C4 C9 C8 -2.2(3) . . . . ?
C5 C4 C9 C10 179.4(2) . . . . ?
C5 C6 C7 C8 49.4(3) . . . . ?
C6 C7 C8 C9 -20.8(3) . . . . ?
C6 C7 C8 C20 155.7(2) . . . . ?
C7 C8 C9 C4 -2.7(3) . . . . ?
C7 C8 C9 C10 175.87(18) . . . . ?
C7 C8 C20 C11 -176.9(2) . . . . ?
C7 C8 C20 C19 -5.5(4) . . . . ?
C8 C9 C10 C1 -179.19(19) . . . . ?
C8 C9 C10 C11 2.5(2) . . . . ?
C9 C4 C5 C6 30.0(3) . . . . ?
C9 C8 C20 C11 -0.1(2) . . . . ?
C9 C8 C20 C19 171.2(2) . . . . ?
C9 C10 C11 C12 -122.8(2) . . . . ?
C9 C10 C11 C20 -2.4(2) . . . . ?
C10 C1 C2 C3 -0.4(3) . . . . ?
C10 C11 C12 C13 178.77(18) . . . . ?
C10 C11 C20 C8 1.5(2) . . . . ?
C10 C11 C20 C19 -171.11(18) . . . . ?
C11 C12 C13 C14 -50.3(2) . . . . ?
C12 C11 C20 C8 127.53(19) . . . . ?
C12 C11 C20 C19 -45.1(2) . . . . ?
C12 C13 C14 C15 -158.3(2) . . . . ?
C12 C13 C14 C19 20.5(3) . . . . ?
C13 C14 C15 C16 178.9(2) . . . . ?
C13 C14 C19 C18 -179.5(2) . . . . ?
C13 C14 C19 C20 -1.4(3) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C14 C19 C20 C8 -156.7(2) . . . . ?
C14 C19 C20 C11 14.2(3) . . . . ?
C15 C14 C19 C18 -0.6(3) . . . . ?
C15 C14 C19 C20 177.50(19) . . . . ?
C15 C16 C17 O2 -179.6(2) . . . . ?
C15 C16 C17 C18 1.1(3) . . . . ?
C16 C17 C18 C19 -1.7(4) . . . . ?
C17 C18 C19 C14 1.4(3) . . . . ?
C17 C18 C19 C20 -176.6(2) . . . . ?
C18 C19 C20 C8 21.3(4) . . . . ?
C18 C19 C20 C11 -167.8(2) . . . . ?
C19 C14 C15 C16 0.0(3) . . . . ?
C20 C8 C9 C4 180.0(2) . . . . ?
C20 C8 C9 C10 -1.5(2) . . . . ?
C20 C11 C12 C13 61.9(2) . . . . ?
C21 O1 C1 C2 -0.1(3) . . . . ?
C21 O1 C1 C10 -179.52(19) . . . . ?
C22 O2 C17 C16 9.4(3) . . . . ?
C22 O2 C17 C18 -171.2(2) . . . . ?

####################################################################### 
# 
# 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 
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data_sa3265
_database_code_depnum_ccdc_archive 'CCDC 1037208'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-02-04 downloaded from the CCDC.
;
_audit_creation_date             2014-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C28 H28 O2'
_chemical_formula_sum            'C28 H28 O2'
_chemical_formula_weight         396.50
_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      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                   8.1661(16)
_cell_length_b                   13.473(3)
_cell_length_c                   20.342(4)
_cell_angle_alpha                98.39(3)
_cell_angle_beta                 94.84(3)
_cell_angle_gamma                99.51(3)
_cell_volume                     2170.1(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6164
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4779
_cell_measurement_theta_min      1.5532
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.231
_exptl_crystal_size_min          0.146
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_av_unetI/netI     0.0917
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21365
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.844
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             9820
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0887
_diffrn_orient_matrix_UB_12      -0.0826
_diffrn_orient_matrix_UB_13      -0.0305
_diffrn_orient_matrix_UB_21      0.0437
_diffrn_orient_matrix_UB_22      0.0429
_diffrn_orient_matrix_UB_23      -0.0455
_diffrn_orient_matrix_UB_31      0.0338
_diffrn_orient_matrix_UB_32      0.0155
_diffrn_orient_matrix_UB_33      0.0334
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7402
_reflns_number_total             9810
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2013)'
_computing_structure_solution    
;
'XS (Sheldrick, 2013)'
;
_refine_diff_density_max         1.353
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     545
_refine_ls_number_reflns         9810
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1327
_refine_ls_R_factor_gt           0.1046
_refine_ls_restrained_S_all      1.157
_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)+(0.0838P)²+1.3402P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2319
_refine_ls_wR_factor_ref         0.2511
_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:
 C21A(H21A,H21B), C22A(H22A,H22B), C23A(H23A,H23B), C25A(H25A,H25B), C26A(H26A,
 H26B), C27A(H27A,H27B), C21(H21C,H21D), C22(H22C,H22D), C23(H23C,H23D),
 C25(H25C,H25D), C26(H26C,H26D), C27(H27C,H27D)
2.b Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A), C7A(H7A), C12A(H12A), C13A(H13A),
 C17A(H17A), C19A(H19A), C20A(H20A), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7),
 C12(H12), C13(H13), C17(H17), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C24A(H24A,H24B,H24C), C28A(H28A,H28B,H28C), C24(H24D,H24E,H24F), C28(H28D,
 H28E,H28F)
;
_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
O1A O -0.1590(3) 0.52669(16) 0.33421(11) 0.0473(5) Uani 1 1 d . . . . .
O2A O 0.1510(3) 1.03821(16) 0.09084(10) 0.0460(5) Uani 1 1 d . . . . .
C1A C -0.0521(4) 0.6124(2) 0.36520(15) 0.0410(7) Uani 1 1 d . . . . .
C2A C 0.0145(4) 0.6284(3) 0.43324(16) 0.0479(8) Uani 1 1 d . . . . .
H2A H -0.0119 0.5767 0.4584 0.058 Uiso 1 1 calc R . . . .
C3A C 0.1158(4) 0.7169(3) 0.46311(15) 0.0473(8) Uani 1 1 d . . . . .
H3A H 0.1563 0.7244 0.5080 0.057 Uiso 1 1 calc R . . . .
C4A C 0.1605(4) 0.7976(2) 0.42702(15) 0.0410(7) Uani 1 1 d . . . . .
C5A C 0.2588(4) 0.8950(2) 0.45093(16) 0.0497(8) Uani 1 1 d . . . . .
H5A H 0.3039 0.9120 0.4955 0.060 Uiso 1 1 calc R . . . .
C6A C 0.2876(4) 0.9645(3) 0.40794(16) 0.0505(8) Uani 1 1 d . . . . .
H6A H 0.3528 1.0281 0.4243 0.061 Uiso 1 1 calc R . . . .
C7A C 0.2217(4) 0.9428(2) 0.33997(16) 0.0456(7) Uani 1 1 d . . . . .
H7A H 0.2440 0.9916 0.3124 0.055 Uiso 1 1 calc R . . . .
C8A C 0.1252(4) 0.8499(2) 0.31461(14) 0.0386(7) Uani 1 1 d . . . . .
C9A C 0.0972(4) 0.7791(2) 0.35960(15) 0.0380(6) Uani 1 1 d . . . . .
C10A C -0.0087(4) 0.6877(2) 0.32809(14) 0.0388(7) Uani 1 1 d . . . . .
C11A C -0.0478(4) 0.7008(2) 0.25795(15) 0.0402(7) Uani 1 1 d . . . . .
C12A C -0.1456(4) 0.6329(2) 0.20468(15) 0.0411(7) Uani 1 1 d . . . . .
H12A H -0.1986 0.5690 0.2111 0.049 Uiso 1 1 calc R . . . .
C13A C -0.1615(4) 0.6617(2) 0.14401(16) 0.0431(7) Uani 1 1 d . . . . .
H13A H -0.2265 0.6168 0.1087 0.052 Uiso 1 1 calc R . . . .
C14A C -0.0811(4) 0.7592(2) 0.13244(14) 0.0387(7) Uani 1 1 d . . . . .
C15A C 0.0178(4) 0.8291(2) 0.18593(14) 0.0365(6) Uani 1 1 d . . . . .
C16A C 0.0327(3) 0.7978(2) 0.25005(14) 0.0370(6) Uani 1 1 d . . . . .
C17A C 0.0986(4) 0.9244(2) 0.17263(14) 0.0374(6) Uani 1 1 d . . . . .
H17A H 0.1660 0.9705 0.2067 0.045 Uiso 1 1 calc R . . . .
C18A C 0.0779(4) 0.9491(2) 0.10979(15) 0.0389(7) Uani 1 1 d . . . . .
C19A C -0.0240(4) 0.8802(2) 0.05710(15) 0.0421(7) Uani 1 1 d . . . . .
H19A H -0.0391 0.8978 0.0148 0.051 Uiso 1 1 calc R . . . .
C20A C -0.0985(4) 0.7888(2) 0.06907(15) 0.0425(7) Uani 1 1 d . . . . .
H20A H -0.1639 0.7436 0.0341 0.051 Uiso 1 1 calc R . . . .
C21A C -0.2074(4) 0.4469(2) 0.37189(15) 0.0421(7) Uani 1 1 d . . . . .
H21A H -0.2618 0.4724 0.4098 0.050 Uiso 1 1 calc R . . . .
H21B H -0.1098 0.4218 0.3885 0.050 Uiso 1 1 calc R . . . .
C22A C -0.3260(4) 0.3623(2) 0.32621(15) 0.0427(7) Uani 1 1 d . . . . .
H22A H -0.4286 0.3861 0.3142 0.051 Uiso 1 1 calc R . . . .
H22B H -0.2763 0.3445 0.2854 0.051 Uiso 1 1 calc R . . . .
C23A C -0.3663(4) 0.2688(2) 0.35868(17) 0.0487(8) Uani 1 1 d . . . . .
H23A H -0.4172 0.2870 0.3991 0.058 Uiso 1 1 calc R . . . .
H23B H -0.2629 0.2465 0.3716 0.058 Uiso 1 1 calc R . . . .
C24A C -0.4824(4) 0.1810(3) 0.3144(2) 0.0576(9) Uani 1 1 d . . . . .
H24A H -0.4356 0.1644 0.2733 0.086 Uiso 1 1 calc GR . . . .
H24B H -0.5890 0.2000 0.3049 0.086 Uiso 1 1 calc GR . . . .
H24C H -0.4961 0.1227 0.3368 0.086 Uiso 1 1 calc GR . . . .
C25A C 0.2586(4) 1.1141(2) 0.13950(15) 0.0400(7) Uani 1 1 d . . . . .
H25A H 0.3562 1.0880 0.1550 0.048 Uiso 1 1 calc R . . . .
H25B H 0.2000 1.1331 0.1776 0.048 Uiso 1 1 calc R . . . .
C26A C 0.3095(4) 1.2046(2) 0.10590(16) 0.0431(7) Uani 1 1 d . . . . .
H26A H 0.2105 1.2306 0.0920 0.052 Uiso 1 1 calc R . . . .
H26B H 0.3601 1.1828 0.0661 0.052 Uiso 1 1 calc R . . . .
C27A C 0.4318(4) 1.2899(2) 0.15049(19) 0.0539(9) Uani 1 1 d . . . . .
H27A H 0.3822 1.3105 0.1908 0.065 Uiso 1 1 calc R . . . .
H27B H 0.5319 1.2643 0.1635 0.065 Uiso 1 1 calc R . . . .
C28A C 0.4795(5) 1.3813(3) 0.1174(2) 0.0754(13) Uani 1 1 d . . . . .
H28A H 0.5348 1.3624 0.0789 0.113 Uiso 1 1 calc GR . . . .
H28B H 0.5534 1.4336 0.1483 0.113 Uiso 1 1 calc GR . . . .
H28C H 0.3809 1.4066 0.1038 0.113 Uiso 1 1 calc GR . . . .
O1 O 0.6795(3) -0.01123(15) 0.16827(10) 0.0452(5) Uani 1 1 d . . . . .
O2 O 1.4142(3) 0.53805(15) 0.41179(10) 0.0432(5) Uani 1 1 d . . . . .
C1 C 0.7322(4) 0.0705(2) 0.13841(15) 0.0388(7) Uani 1 1 d . . . . .
C2 C 0.6805(4) 0.0771(2) 0.07157(15) 0.0433(7) Uani 1 1 d . . . . .
H2 H 0.6106 0.0213 0.0454 0.052 Uiso 1 1 calc R . . . .
C3 C 0.7290(4) 0.1620(2) 0.04369(15) 0.0425(7) Uani 1 1 d . . . . .
H3 H 0.6920 0.1629 -0.0007 0.051 Uiso 1 1 calc R . . . .
C4 C 0.8349(4) 0.2486(2) 0.08166(14) 0.0366(6) Uani 1 1 d . . . . .
C5 C 0.8933(4) 0.3435(2) 0.06107(16) 0.0440(7) Uani 1 1 d . . . . .
H5 H 0.8634 0.3536 0.0177 0.053 Uiso 1 1 calc R . . . .
C6 C 0.9939(4) 0.4196(2) 0.10563(16) 0.0449(7) Uani 1 1 d . . . . .
H6 H 1.0311 0.4813 0.0916 0.054 Uiso 1 1 calc R . . . .
C7 C 1.0441(4) 0.4087(2) 0.17233(15) 0.0396(7) Uani 1 1 d . . . . .
H7 H 1.1101 0.4630 0.2014 0.047 Uiso 1 1 calc R . . . .
C8 C 0.9943(3) 0.3176(2) 0.19351(14) 0.0353(6) Uani 1 1 d . . . . .
C9 C 0.8880(3) 0.2397(2) 0.14733(14) 0.0348(6) Uani 1 1 d . . . . .
C10 C 0.8401(4) 0.1516(2) 0.17616(14) 0.0360(6) Uani 1 1 d . . . . .
C11 C 0.9257(3) 0.1743(2) 0.24492(14) 0.0366(6) Uani 1 1 d . . . . .
C12 C 0.9266(4) 0.1127(2) 0.29487(15) 0.0385(7) Uani 1 1 d . . . . .
H12 H 0.8648 0.0468 0.2869 0.046 Uiso 1 1 calc R . . . .
C13 C 1.0177(4) 0.1494(2) 0.35473(15) 0.0392(7) Uani 1 1 d . . . . .
H13 H 1.0179 0.1083 0.3877 0.047 Uiso 1 1 calc R . . . .
C14 C 1.1137(4) 0.2506(2) 0.36797(14) 0.0362(6) Uani 1 1 d . . . . .
C15 C 1.1165(3) 0.3146(2) 0.31787(14) 0.0339(6) Uani 1 1 d . . . . .
C16 C 1.0183(3) 0.2737(2) 0.25542(14) 0.0336(6) Uani 1 1 d . . . . .
C17 C 1.2170(3) 0.4129(2) 0.33218(14) 0.0353(6) Uani 1 1 d . . . . .
H17 H 1.2199 0.4554 0.3000 0.042 Uiso 1 1 calc R . . . .
C18 C 1.3102(4) 0.4462(2) 0.39325(14) 0.0372(6) Uani 1 1 d . . . . .
C19 C 1.3049(4) 0.3830(2) 0.44291(15) 0.0406(7) Uani 1 1 d . . . . .
H19 H 1.3658 0.4063 0.4846 0.049 Uiso 1 1 calc R . . . .
C20 C 1.2105(4) 0.2881(2) 0.42955(15) 0.0417(7) Uani 1 1 d . . . . .
H20 H 1.2100 0.2466 0.4623 0.050 Uiso 1 1 calc R . . . .
C21 C 0.5624(4) -0.0947(2) 0.13056(15) 0.0408(7) Uani 1 1 d . . . . .
H21C H 0.6111 -0.1248 0.0923 0.049 Uiso 1 1 calc R . . . .
H21D H 0.4631 -0.0709 0.1143 0.049 Uiso 1 1 calc R . . . .
C22 C 0.5172(4) -0.1722(2) 0.17451(16) 0.0429(7) Uani 1 1 d . . . . .
H22C H 0.4619 -0.1427 0.2109 0.051 Uiso 1 1 calc R . . . .
H22D H 0.6183 -0.1910 0.1937 0.051 Uiso 1 1 calc R . . . .
C23 C 0.4032(4) -0.2669(2) 0.13629(18) 0.0507(8) Uani 1 1 d . . . . .
H23C H 0.3018 -0.2477 0.1178 0.061 Uiso 1 1 calc R . . . .
H23D H 0.4580 -0.2950 0.0993 0.061 Uiso 1 1 calc R . . . .
C24 C 0.3575(5) -0.3476(3) 0.1784(2) 0.0621(10) Uani 1 1 d . . . . .
H24D H 0.2892 -0.4065 0.1510 0.093 Uiso 1 1 calc GR . . . .
H24E H 0.2967 -0.3219 0.2135 0.093 Uiso 1 1 calc GR . . . .
H24F H 0.4573 -0.3662 0.1975 0.093 Uiso 1 1 calc GR . . . .
C25 C 1.4330(4) 0.6073(2) 0.36441(15) 0.0404(7) Uani 1 1 d . . . . .
H25C H 1.3259 0.6246 0.3507 0.048 Uiso 1 1 calc R . . . .
H25D H 1.4766 0.5764 0.3250 0.048 Uiso 1 1 calc R . . . .
C26 C 1.5528(4) 0.7013(2) 0.39860(15) 0.0418(7) Uani 1 1 d . . . . .
H26C H 1.6577 0.6821 0.4131 0.050 Uiso 1 1 calc R . . . .
H26D H 1.5077 0.7305 0.4381 0.050 Uiso 1 1 calc R . . . .
C27 C 1.5860(4) 0.7812(2) 0.35405(17) 0.0486(8) Uani 1 1 d . . . . .
H27C H 1.4807 0.7988 0.3383 0.058 Uiso 1 1 calc R . . . .
H27D H 1.6348 0.7529 0.3153 0.058 Uiso 1 1 calc R . . . .
C28 C 1.7020(5) 0.8772(3) 0.3893(2) 0.0638(10) Uani 1 1 d . . . . .
H28D H 1.7164 0.9260 0.3593 0.096 Uiso 1 1 calc GR . . . .
H28E H 1.8084 0.8609 0.4030 0.096 Uiso 1 1 calc GR . . . .
H28F H 1.6547 0.9055 0.4278 0.096 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
O1A C1A 1.362(4) . ?
O1A C21A 1.432(3) . ?
O2A C18A 1.372(3) . ?
O2A C25A 1.434(3) . ?
C1A C2A 1.416(5) . ?
C1A C10A 1.370(4) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.361(5) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.415(4) . ?
C4A C5A 1.415(4) . ?
C4A C9A 1.396(4) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.378(4) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.411(4) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.367(4) . ?
C8A C9A 1.420(4) . ?
C8A C16A 1.475(4) . ?
C9A C10A 1.414(4) . ?
C10A C11A 1.478(4) . ?
C11A C12A 1.404(4) . ?
C11A C16A 1.401(4) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.349(4) . ?
C13A H13A 0.9300 . ?
C13A C14A 1.430(4) . ?
C14A C15A 1.423(4) . ?
C14A C20A 1.407(4) . ?
C15A C16A 1.430(4) . ?
C15A C17A 1.418(4) . ?
C17A H17A 0.9300 . ?
C17A C18A 1.371(4) . ?
C18A C19A 1.417(4) . ?
C19A H19A 0.9300 . ?
C19A C20A 1.345(4) . ?
C20A H20A 0.9300 . ?
C21A H21A 0.9700 . ?
C21A H21B 0.9700 . ?
C21A C22A 1.508(4) . ?
C22A H22A 0.9700 . ?
C22A H22B 0.9700 . ?
C22A C23A 1.508(4) . ?
C23A H23A 0.9700 . ?
C23A H23B 0.9700 . ?
C23A C24A 1.512(5) . ?
C24A H24A 0.9600 . ?
C24A H24B 0.9600 . ?
C24A H24C 0.9600 . ?
C25A H25A 0.9700 . ?
C25A H25B 0.9700 . ?
C25A C26A 1.500(4) . ?
C26A H26A 0.9700 . ?
C26A H26B 0.9700 . ?
C26A C27A 1.518(4) . ?
C27A H27A 0.9700 . ?
C27A H27B 0.9700 . ?
C27A C28A 1.500(5) . ?
C28A H28A 0.9600 . ?
C28A H28B 0.9600 . ?
C28A H28C 0.9600 . ?
O1 C1 1.360(3) . ?
O1 C21 1.427(3) . ?
O2 C18 1.362(3) . ?
O2 C25 1.436(3) . ?
C1 C2 1.409(4) . ?
C1 C10 1.372(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.366(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.413(4) . ?
C4 C5 1.423(4) . ?
C4 C9 1.398(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.369(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.419(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.370(4) . ?
C8 C9 1.419(4) . ?
C8 C16 1.480(4) . ?
C9 C10 1.411(4) . ?
C10 C11 1.476(4) . ?
C11 C12 1.403(4) . ?
C11 C16 1.402(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.353(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.432(4) . ?
C14 C15 1.426(4) . ?
C14 C20 1.402(4) . ?
C15 C16 1.428(4) . ?
C15 C17 1.415(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.375(4) . ?
C18 C19 1.412(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.356(4) . ?
C20 H20 0.9300 . ?
C21 H21C 0.9700 . ?
C21 H21D 0.9700 . ?
C21 C22 1.492(4) . ?
C22 H22C 0.9700 . ?
C22 H22D 0.9700 . ?
C22 C23 1.515(4) . ?
C23 H23C 0.9700 . ?
C23 H23D 0.9700 . ?
C23 C24 1.499(5) . ?
C24 H24D 0.9600 . ?
C24 H24E 0.9600 . ?
C24 H24F 0.9600 . ?
C25 H25C 0.9700 . ?
C25 H25D 0.9700 . ?
C25 C26 1.505(4) . ?
C26 H26C 0.9700 . ?
C26 H26D 0.9700 . ?
C26 C27 1.511(4) . ?
C27 H27C 0.9700 . ?
C27 H27D 0.9700 . ?
C27 C28 1.514(4) . ?
C28 H28D 0.9600 . ?
C28 H28E 0.9600 . ?
C28 H28F 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
C1A O1A C21A 118.8(2) . . ?
C18A O2A C25A 119.1(2) . . ?
O1A C1A C2A 123.9(3) . . ?
O1A C1A C10A 117.5(3) . . ?
C10A C1A C2A 118.5(3) . . ?
C1A C2A H2A 118.9 . . ?
C3A C2A C1A 122.2(3) . . ?
C3A C2A H2A 118.9 . . ?
C2A C3A H3A 119.4 . . ?
C2A C3A C4A 121.2(3) . . ?
C4A C3A H3A 119.4 . . ?
C3A C4A C5A 128.2(3) . . ?
C9A C4A C3A 115.7(3) . . ?
C9A C4A C5A 116.1(3) . . ?
C4A C5A H5A 120.1 . . ?
C6A C5A C4A 119.8(3) . . ?
C6A C5A H5A 120.1 . . ?
C5A C6A H6A 118.8 . . ?
C5A C6A C7A 122.4(3) . . ?
C7A C6A H6A 118.8 . . ?
C6A C7A H7A 120.0 . . ?
C8A C7A C6A 120.0(3) . . ?
C8A C7A H7A 120.0 . . ?
C7A C8A C9A 116.8(3) . . ?
C7A C8A C16A 137.6(3) . . ?
C9A C8A C16A 105.5(2) . . ?
C4A C9A C8A 124.9(3) . . ?
C4A C9A C10A 123.7(3) . . ?
C10A C9A C8A 111.4(3) . . ?
C1A C10A C9A 118.8(3) . . ?
C1A C10A C11A 135.3(3) . . ?
C9A C10A C11A 105.9(3) . . ?
C12A C11A C10A 129.7(3) . . ?
C16A C11A C10A 108.3(3) . . ?
C16A C11A C12A 121.9(3) . . ?
C11A C12A H12A 120.5 . . ?
C13A C12A C11A 119.0(3) . . ?
C13A C12A H12A 120.5 . . ?
C12A C13A H13A 119.1 . . ?
C12A C13A C14A 121.8(3) . . ?
C14A C13A H13A 119.1 . . ?
C15A C14A C13A 119.9(3) . . ?
C20A C14A C13A 121.5(3) . . ?
C20A C14A C15A 118.6(3) . . ?
C14A C15A C16A 117.7(3) . . ?
C17A C15A C14A 118.6(3) . . ?
C17A C15A C16A 123.7(3) . . ?
C11A C16A C8A 108.8(3) . . ?
C11A C16A C15A 119.6(3) . . ?
C15A C16A C8A 131.5(3) . . ?
C15A C17A H17A 119.8 . . ?
C18A C17A C15A 120.3(3) . . ?
C18A C17A H17A 119.8 . . ?
O2A C18A C19A 113.6(3) . . ?
C17A C18A O2A 125.5(3) . . ?
C17A C18A C19A 120.8(3) . . ?
C18A C19A H19A 120.4 . . ?
C20A C19A C18A 119.2(3) . . ?
C20A C19A H19A 120.4 . . ?
C14A C20A H20A 118.8 . . ?
C19A C20A C14A 122.5(3) . . ?
C19A C20A H20A 118.8 . . ?
O1A C21A H21A 110.1 . . ?
O1A C21A H21B 110.1 . . ?
O1A C21A C22A 107.9(2) . . ?
H21A C21A H21B 108.4 . . ?
C22A C21A H21A 110.1 . . ?
C22A C21A H21B 110.1 . . ?
C21A C22A H22A 109.3 . . ?
C21A C22A H22B 109.3 . . ?
H22A C22A H22B 107.9 . . ?
C23A C22A C21A 111.8(3) . . ?
C23A C22A H22A 109.3 . . ?
C23A C22A H22B 109.3 . . ?
C22A C23A H23A 108.8 . . ?
C22A C23A H23B 108.8 . . ?
C22A C23A C24A 113.9(3) . . ?
H23A C23A H23B 107.7 . . ?
C24A C23A H23A 108.8 . . ?
C24A C23A H23B 108.8 . . ?
C23A C24A H24A 109.5 . . ?
C23A C24A H24B 109.5 . . ?
C23A C24A H24C 109.5 . . ?
H24A C24A H24B 109.5 . . ?
H24A C24A H24C 109.5 . . ?
H24B C24A H24C 109.5 . . ?
O2A C25A H25A 110.3 . . ?
O2A C25A H25B 110.3 . . ?
O2A C25A C26A 107.0(2) . . ?
H25A C25A H25B 108.6 . . ?
C26A C25A H25A 110.3 . . ?
C26A C25A H25B 110.3 . . ?
C25A C26A H26A 108.9 . . ?
C25A C26A H26B 108.9 . . ?
C25A C26A C27A 113.2(3) . . ?
H26A C26A H26B 107.8 . . ?
C27A C26A H26A 108.9 . . ?
C27A C26A H26B 108.9 . . ?
C26A C27A H27A 109.0 . . ?
C26A C27A H27B 109.0 . . ?
H27A C27A H27B 107.8 . . ?
C28A C27A C26A 113.1(3) . . ?
C28A C27A H27A 109.0 . . ?
C28A C27A H27B 109.0 . . ?
C27A C28A H28A 109.5 . . ?
C27A C28A H28B 109.5 . . ?
C27A C28A H28C 109.5 . . ?
H28A C28A H28B 109.5 . . ?
H28A C28A H28C 109.5 . . ?
H28B C28A H28C 109.5 . . ?
C1 O1 C21 118.5(2) . . ?
C18 O2 C25 118.9(2) . . ?
O1 C1 C2 123.8(3) . . ?
O1 C1 C10 117.8(3) . . ?
C10 C1 C2 118.4(3) . . ?
C1 C2 H2 118.7 . . ?
C3 C2 C1 122.7(3) . . ?
C3 C2 H2 118.7 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 127.8(3) . . ?
C9 C4 C3 115.8(3) . . ?
C9 C4 C5 116.4(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 H6 118.5 . . ?
C5 C6 C7 123.0(3) . . ?
C7 C6 H6 118.5 . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.4(3) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 C9 117.2(3) . . ?
C7 C8 C16 137.3(3) . . ?
C9 C8 C16 105.5(2) . . ?
C4 C9 C8 124.6(3) . . ?
C4 C9 C10 123.8(3) . . ?
C10 C9 C8 111.6(3) . . ?
C1 C10 C9 118.6(3) . . ?
C1 C10 C11 135.6(3) . . ?
C9 C10 C11 105.9(2) . . ?
C12 C11 C10 130.0(3) . . ?
C16 C11 C10 108.6(3) . . ?
C16 C11 C12 121.4(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 120.9(3) . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 120.5(3) . . ?
C20 C14 C13 121.0(3) . . ?
C20 C14 C15 118.5(3) . . ?
C14 C15 C16 117.2(2) . . ?
C17 C15 C14 118.8(3) . . ?
C17 C15 C16 124.0(3) . . ?
C11 C16 C8 108.5(2) . . ?
C11 C16 C15 120.3(3) . . ?
C15 C16 C8 131.3(3) . . ?
C15 C17 H17 119.7 . . ?
C18 C17 C15 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
O2 C18 C17 125.6(3) . . ?
O2 C18 C19 114.2(3) . . ?
C17 C18 C19 120.3(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.7(3) . . ?
C20 C19 H19 120.1 . . ?
C14 C20 H20 118.9 . . ?
C19 C20 C14 122.1(3) . . ?
C19 C20 H20 118.9 . . ?
O1 C21 H21C 109.9 . . ?
O1 C21 H21D 109.9 . . ?
O1 C21 C22 108.8(2) . . ?
H21C C21 H21D 108.3 . . ?
C22 C21 H21C 109.9 . . ?
C22 C21 H21D 109.9 . . ?
C21 C22 H22C 109.3 . . ?
C21 C22 H22D 109.3 . . ?
C21 C22 C23 111.7(3) . . ?
H22C C22 H22D 107.9 . . ?
C23 C22 H22C 109.3 . . ?
C23 C22 H22D 109.3 . . ?
C22 C23 H23C 108.9 . . ?
C22 C23 H23D 108.9 . . ?
H23C C23 H23D 107.7 . . ?
C24 C23 C22 113.4(3) . . ?
C24 C23 H23C 108.9 . . ?
C24 C23 H23D 108.9 . . ?
C23 C24 H24D 109.5 . . ?
C23 C24 H24E 109.5 . . ?
C23 C24 H24F 109.5 . . ?
H24D C24 H24E 109.5 . . ?
H24D C24 H24F 109.5 . . ?
H24E C24 H24F 109.5 . . ?
O2 C25 H25C 110.3 . . ?
O2 C25 H25D 110.3 . . ?
O2 C25 C26 107.0(2) . . ?
H25C C25 H25D 108.6 . . ?
C26 C25 H25C 110.3 . . ?
C26 C25 H25D 110.3 . . ?
C25 C26 H26C 109.0 . . ?
C25 C26 H26D 109.0 . . ?
C25 C26 C27 112.9(3) . . ?
H26C C26 H26D 107.8 . . ?
C27 C26 H26C 109.0 . . ?
C27 C26 H26D 109.0 . . ?
C26 C27 H27C 109.0 . . ?
C26 C27 H27D 109.0 . . ?
C26 C27 C28 112.8(3) . . ?
H27C C27 H27D 107.8 . . ?
C28 C27 H27C 109.0 . . ?
C28 C27 H27D 109.0 . . ?
C27 C28 H28D 109.5 . . ?
C27 C28 H28E 109.5 . . ?
C27 C28 H28F 109.5 . . ?
H28D C28 H28E 109.5 . . ?
H28D C28 H28F 109.5 . . ?
H28E C28 H28F 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
O1A C1A C2A C3A -177.3(3) . . . . ?
O1A C1A C10A C9A 177.7(2) . . . . ?
O1A C1A C10A C11A -1.3(5) . . . . ?
O1A C21A C22A C23A 172.4(2) . . . . ?
O2A C18A C19A C20A 178.1(3) . . . . ?
O2A C25A C26A C27A -177.0(2) . . . . ?
C1A O1A C21A C22A 179.6(2) . . . . ?
C1A C2A C3A C4A -0.4(5) . . . . ?
C1A C10A C11A C12A -1.9(6) . . . . ?
C1A C10A C11A C16A 178.5(3) . . . . ?
C2A C1A C10A C9A -1.6(4) . . . . ?
C2A C1A C10A C11A 179.4(3) . . . . ?
C2A C3A C4A C5A 177.6(3) . . . . ?
C2A C3A C4A C9A -1.3(5) . . . . ?
C3A C4A C5A C6A -179.3(3) . . . . ?
C3A C4A C9A C8A 179.3(3) . . . . ?
C3A C4A C9A C10A 1.6(4) . . . . ?
C4A C5A C6A C7A 0.2(5) . . . . ?
C4A C9A C10A C1A -0.2(4) . . . . ?
C4A C9A C10A C11A 179.1(3) . . . . ?
C5A C4A C9A C8A 0.4(4) . . . . ?
C5A C4A C9A C10A -177.4(3) . . . . ?
C5A C6A C7A C8A 0.1(5) . . . . ?
C6A C7A C8A C9A -0.2(4) . . . . ?
C6A C7A C8A C16A 178.6(3) . . . . ?
C7A C8A C9A C4A 0.0(4) . . . . ?
C7A C8A C9A C10A 178.0(3) . . . . ?
C7A C8A C16A C11A -178.1(4) . . . . ?
C7A C8A C16A C15A 3.2(6) . . . . ?
C8A C9A C10A C1A -178.2(3) . . . . ?
C8A C9A C10A C11A 1.1(3) . . . . ?
C9A C4A C5A C6A -0.5(5) . . . . ?
C9A C8A C16A C11A 0.8(3) . . . . ?
C9A C8A C16A C15A -177.9(3) . . . . ?
C9A C10A C11A C12A 179.0(3) . . . . ?
C9A C10A C11A C16A -0.6(3) . . . . ?
C10A C1A C2A C3A 1.9(5) . . . . ?
C10A C11A C12A C13A -179.0(3) . . . . ?
C10A C11A C16A C8A -0.1(3) . . . . ?
C10A C11A C16A C15A 178.7(2) . . . . ?
C11A C12A C13A C14A 0.2(5) . . . . ?
C12A C11A C16A C8A -179.7(3) . . . . ?
C12A C11A C16A C15A -0.9(4) . . . . ?
C12A C13A C14A C15A -0.5(5) . . . . ?
C12A C13A C14A C20A -179.9(3) . . . . ?
C13A C14A C15A C16A 0.1(4) . . . . ?
C13A C14A C15A C17A 178.8(3) . . . . ?
C13A C14A C20A C19A -180.0(3) . . . . ?
C14A C15A C16A C8A 179.2(3) . . . . ?
C14A C15A C16A C11A 0.6(4) . . . . ?
C14A C15A C17A C18A 1.5(4) . . . . ?
C15A C14A C20A C19A 0.6(5) . . . . ?
C15A C17A C18A O2A -179.2(3) . . . . ?
C15A C17A C18A C19A -0.1(4) . . . . ?
C16A C8A C9A C4A -179.2(3) . . . . ?
C16A C8A C9A C10A -1.2(3) . . . . ?
C16A C11A C12A C13A 0.5(5) . . . . ?
C16A C15A C17A C18A -179.8(3) . . . . ?
C17A C15A C16A C8A 0.5(5) . . . . ?
C17A C15A C16A C11A -178.1(3) . . . . ?
C17A C18A C19A C20A -1.1(4) . . . . ?
C18A O2A C25A C26A -176.1(2) . . . . ?
C18A C19A C20A C14A 0.9(5) . . . . ?
C20A C14A C15A C16A 179.5(3) . . . . ?
C20A C14A C15A C17A -1.8(4) . . . . ?
C21A O1A C1A C2A -0.4(4) . . . . ?
C21A O1A C1A C10A -179.6(3) . . . . ?
C21A C22A C23A C24A -178.9(3) . . . . ?
C25A O2A C18A C17A -0.3(4) . . . . ?
C25A O2A C18A C19A -179.4(2) . . . . ?
C25A C26A C27A C28A -178.6(3) . . . . ?
O1 C1 C2 C3 176.8(3) . . . . ?
O1 C1 C10 C9 -176.1(2) . . . . ?
O1 C1 C10 C11 3.0(5) . . . . ?
O1 C21 C22 C23 -175.6(2) . . . . ?
O2 C18 C19 C20 -177.6(3) . . . . ?
O2 C25 C26 C27 179.5(2) . . . . ?
C1 O1 C21 C22 -177.2(2) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C1 C10 C11 C12 3.1(5) . . . . ?
C1 C10 C11 C16 -178.3(3) . . . . ?
C2 C1 C10 C9 3.0(4) . . . . ?
C2 C1 C10 C11 -177.9(3) . . . . ?
C2 C3 C4 C5 -178.3(3) . . . . ?
C2 C3 C4 C9 1.6(4) . . . . ?
C3 C4 C5 C6 179.0(3) . . . . ?
C3 C4 C9 C8 180.0(3) . . . . ?
C3 C4 C9 C10 -0.8(4) . . . . ?
C4 C5 C6 C7 0.1(5) . . . . ?
C4 C9 C10 C1 -1.5(4) . . . . ?
C4 C9 C10 C11 179.2(3) . . . . ?
C5 C4 C9 C8 -0.1(4) . . . . ?
C5 C4 C9 C10 179.1(3) . . . . ?
C5 C6 C7 C8 1.7(5) . . . . ?
C6 C7 C8 C9 -2.6(4) . . . . ?
C6 C7 C8 C16 178.8(3) . . . . ?
C7 C8 C9 C4 1.9(4) . . . . ?
C7 C8 C9 C10 -177.4(2) . . . . ?
C7 C8 C16 C11 177.7(3) . . . . ?
C7 C8 C16 C15 -3.6(5) . . . . ?
C8 C9 C10 C1 177.8(2) . . . . ?
C8 C9 C10 C11 -1.6(3) . . . . ?
C9 C4 C5 C6 -0.9(4) . . . . ?
C9 C8 C16 C11 -1.0(3) . . . . ?
C9 C8 C16 C15 177.7(3) . . . . ?
C9 C10 C11 C12 -177.8(3) . . . . ?
C9 C10 C11 C16 0.9(3) . . . . ?
C10 C1 C2 C3 -2.2(5) . . . . ?
C10 C11 C12 C13 178.8(3) . . . . ?
C10 C11 C16 C8 0.1(3) . . . . ?
C10 C11 C16 C15 -178.8(2) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C12 C11 C16 C8 178.9(2) . . . . ?
C12 C11 C16 C15 0.0(4) . . . . ?
C12 C13 C14 C15 -0.6(4) . . . . ?
C12 C13 C14 C20 -178.9(3) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C13 C14 C15 C17 -178.1(3) . . . . ?
C13 C14 C20 C19 178.8(3) . . . . ?
C14 C15 C16 C8 -179.2(3) . . . . ?
C14 C15 C16 C11 -0.6(4) . . . . ?
C14 C15 C17 C18 0.0(4) . . . . ?
C15 C14 C20 C19 0.5(4) . . . . ?
C15 C17 C18 O2 178.3(3) . . . . ?
C15 C17 C18 C19 -0.9(4) . . . . ?
C16 C8 C9 C4 -179.1(3) . . . . ?
C16 C8 C9 C10 1.6(3) . . . . ?
C16 C11 C12 C13 0.3(4) . . . . ?
C16 C15 C17 C18 -178.9(3) . . . . ?
C17 C15 C16 C8 -0.3(5) . . . . ?
C17 C15 C16 C11 178.3(3) . . . . ?
C17 C18 C19 C20 1.6(4) . . . . ?
C18 O2 C25 C26 179.6(2) . . . . ?
C18 C19 C20 C14 -1.4(5) . . . . ?
C20 C14 C15 C16 179.2(3) . . . . ?
C20 C14 C15 C17 0.2(4) . . . . ?
C21 O1 C1 C2 -1.4(4) . . . . ?
C21 O1 C1 C10 177.7(2) . . . . ?
C21 C22 C23 C24 178.9(3) . . . . ?
C25 O2 C18 C17 -1.0(4) . . . . ?
C25 O2 C18 C19 178.2(2) . . . . ?
C25 C26 C27 C28 178.0(3) . . . . ?

####################################################################### 
# 
# 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_sa3097
_database_code_depnum_ccdc_archive 'CCDC 1037219'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-02-04 downloaded from the CCDC.
;
_audit_creation_date             2013-12-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H16 O2'
_chemical_formula_sum            'C22 H16 O2'
_chemical_formula_weight         312.35
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   10.361(2)
_cell_length_b                   14.6319(7)
_cell_length_c                   20.1158(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3049.4(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8634
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4843
_cell_measurement_theta_min      1.3917
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.26
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11528
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.823
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             3918
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0964
_diffrn_orient_matrix_UB_12      0.0037
_diffrn_orient_matrix_UB_13      -0.0018
_diffrn_orient_matrix_UB_21      0.0029
_diffrn_orient_matrix_UB_22      0.0649
_diffrn_orient_matrix_UB_23      -0.0214
_diffrn_orient_matrix_UB_31      0.0003
_diffrn_orient_matrix_UB_32      -0.0156
_diffrn_orient_matrix_UB_33      -0.0472
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3264
_reflns_number_total             3474
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
'XL (Sheldrick, 2008)'
;
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3474
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0625
_refine_ls_restrained_S_all      1.224
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0294P)²+1.4953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1250
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C15(H15), C16(H16), C17(H17),
 C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.69403(12) 0.41971(8) 0.70047(6) 0.0357(3) Uani 1 1 d . . . . .
O2 O 0.05233(14) 0.47658(10) 0.38552(7) 0.0445(4) Uani 1 1 d . . . . .
C1 C 0.62065(16) 0.49705(12) 0.69924(8) 0.0290(4) Uani 1 1 d . . . . .
C2 C 0.63621(17) 0.57021(12) 0.74501(9) 0.0329(4) Uani 1 1 d . . . . .
H2 H 0.7003 0.5663 0.7772 0.040 Uiso 1 1 calc R . . . .
C3 C 0.55904(18) 0.64664(12) 0.74292(9) 0.0333(4) Uani 1 1 d . . . . .
H3 H 0.5709 0.6927 0.7742 0.040 Uiso 1 1 calc R . . . .
C4 C 0.46184(17) 0.65632(12) 0.69399(8) 0.0288(4) Uani 1 1 d . . . . .
C5 C 0.37730(18) 0.73109(12) 0.68472(9) 0.0331(4) Uani 1 1 d . . . . .
H5 H 0.3820 0.7815 0.7128 0.040 Uiso 1 1 calc R . . . .
C6 C 0.28815(18) 0.72912(12) 0.63418(9) 0.0341(4) Uani 1 1 d . . . . .
H6 H 0.2344 0.7793 0.6282 0.041 Uiso 1 1 calc R . . . .
C7 C 0.27520(17) 0.65308(12) 0.59074(8) 0.0311(4) Uani 1 1 d . . . . .
H7 H 0.2129 0.6535 0.5575 0.037 Uiso 1 1 calc R . . . .
C8 C 0.35537(16) 0.57886(11) 0.59818(8) 0.0270(4) Uani 1 1 d . . . . .
C9 C 0.44855(16) 0.58276(11) 0.65017(8) 0.0265(4) Uani 1 1 d . . . . .
C10 C 0.52493(16) 0.50359(11) 0.65142(8) 0.0270(4) Uani 1 1 d . . . . .
C11 C 0.47835(16) 0.44481(12) 0.59744(8) 0.0275(4) Uani 1 1 d . . . . .
C12 C 0.37580(16) 0.48968(11) 0.56505(8) 0.0263(4) Uani 1 1 d . . . . .
C13 C 0.31345(16) 0.44783(11) 0.50992(8) 0.0279(4) Uani 1 1 d . . . . .
C14 C 0.35868(17) 0.35986(12) 0.48975(9) 0.0309(4) Uani 1 1 d . . . . .
C15 C 0.46322(18) 0.31807(12) 0.52308(9) 0.0329(4) Uani 1 1 d . . . . .
H15 H 0.4925 0.2614 0.5086 0.040 Uiso 1 1 calc R . . . .
C16 C 0.52251(17) 0.35901(12) 0.57622(9) 0.0311(4) Uani 1 1 d . . . . .
H16 H 0.5908 0.3304 0.5978 0.037 Uiso 1 1 calc R . . . .
C17 C 0.21055(17) 0.48905(12) 0.47434(8) 0.0308(4) Uani 1 1 d . . . . .
H17 H 0.1817 0.5469 0.4865 0.037 Uiso 1 1 calc R . . . .
C18 C 0.15333(18) 0.44435(13) 0.42224(9) 0.0340(4) Uani 1 1 d . . . . .
C19 C 0.1974(2) 0.35717(13) 0.40234(9) 0.0388(5) Uani 1 1 d . . . . .
H19 H 0.1581 0.3273 0.3669 0.047 Uiso 1 1 calc R . . . .
C20 C 0.29696(19) 0.31714(13) 0.43489(9) 0.0369(4) Uani 1 1 d . . . . .
H20 H 0.3257 0.2601 0.4209 0.044 Uiso 1 1 calc R . . . .
C21 C 0.80333(18) 0.41843(13) 0.74409(10) 0.0382(4) Uani 1 1 d . . . . .
H21A H 0.7745 0.4233 0.7893 0.057 Uiso 1 1 calc GR . . . .
H21B H 0.8590 0.4689 0.7338 0.057 Uiso 1 1 calc GR . . . .
H21C H 0.8497 0.3622 0.7384 0.057 Uiso 1 1 calc GR . . . .
C22 C 0.0100(2) 0.56745(14) 0.39803(10) 0.0446(5) Uani 1 1 d . . . . .
H22A H -0.0190 0.5723 0.4432 0.067 Uiso 1 1 calc GR . . . .
H22B H -0.0597 0.5822 0.3685 0.067 Uiso 1 1 calc GR . . . .
H22C H 0.0802 0.6091 0.3908 0.067 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 1.363(2) . ?
O1 C21 1.433(2) . ?
O2 C18 1.365(2) . ?
O2 C22 1.422(2) . ?
C1 C2 1.421(2) . ?
C1 C10 1.385(2) . ?
C2 C3 1.375(3) . ?
C3 C4 1.415(2) . ?
C4 C5 1.414(2) . ?
C4 C9 1.398(2) . ?
C5 C6 1.374(3) . ?
C6 C7 1.421(2) . ?
C7 C8 1.375(2) . ?
C8 C9 1.424(2) . ?
C8 C12 1.480(2) . ?
C9 C10 1.403(2) . ?
C10 C11 1.467(2) . ?
C11 C12 1.409(2) . ?
C11 C16 1.403(2) . ?
C12 C13 1.422(2) . ?
C13 C14 1.429(2) . ?
C13 C17 1.419(2) . ?
C14 C15 1.413(3) . ?
C14 C20 1.421(2) . ?
C15 C16 1.371(3) . ?
C17 C18 1.370(2) . ?
C18 C19 1.413(3) . ?
C19 C20 1.355(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C21 117.56(14) . . ?
C18 O2 C22 117.61(15) . . ?
O1 C1 C2 123.38(15) . . ?
O1 C1 C10 117.98(16) . . ?
C10 C1 C2 118.63(16) . . ?
C3 C2 C1 121.79(16) . . ?
C2 C3 C4 121.08(16) . . ?
C5 C4 C3 127.59(16) . . ?
C9 C4 C3 115.56(16) . . ?
C9 C4 C5 116.85(16) . . ?
C6 C5 C4 119.86(16) . . ?
C5 C6 C7 122.33(17) . . ?
C8 C7 C6 119.63(16) . . ?
C7 C8 C9 117.23(15) . . ?
C7 C8 C12 137.18(16) . . ?
C9 C8 C12 105.59(14) . . ?
C4 C9 C8 124.09(16) . . ?
C4 C9 C10 124.67(16) . . ?
C10 C9 C8 111.24(15) . . ?
C1 C10 C9 118.26(16) . . ?
C1 C10 C11 135.17(16) . . ?
C9 C10 C11 106.57(14) . . ?
C12 C11 C10 108.50(15) . . ?
C16 C11 C10 130.00(16) . . ?
C16 C11 C12 121.49(16) . . ?
C11 C12 C8 108.09(14) . . ?
C11 C12 C13 120.18(15) . . ?
C13 C12 C8 131.73(16) . . ?
C12 C13 C14 117.41(16) . . ?
C17 C13 C12 123.49(16) . . ?
C17 C13 C14 119.09(16) . . ?
C15 C14 C13 120.44(16) . . ?
C15 C14 C20 121.55(17) . . ?
C20 C14 C13 118.00(17) . . ?
C16 C15 C14 121.62(17) . . ?
C15 C16 C11 118.84(17) . . ?
C18 C17 C13 120.54(17) . . ?
O2 C18 C17 125.50(18) . . ?
O2 C18 C19 113.98(16) . . ?
C17 C18 C19 120.52(18) . . ?
C20 C19 C18 119.97(17) . . ?
C19 C20 C14 121.86(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -178.96(16) . . . . ?
O1 C1 C10 C9 179.60(14) . . . . ?
O1 C1 C10 C11 -0.3(3) . . . . ?
O2 C18 C19 C20 -179.75(17) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C1 C10 C11 C12 179.96(18) . . . . ?
C1 C10 C11 C16 -1.5(3) . . . . ?
C2 C1 C10 C9 0.6(2) . . . . ?
C2 C1 C10 C11 -179.31(18) . . . . ?
C2 C3 C4 C5 -178.63(17) . . . . ?
C2 C3 C4 C9 1.6(3) . . . . ?
C3 C4 C5 C6 179.87(18) . . . . ?
C3 C4 C9 C8 179.12(16) . . . . ?
C3 C4 C9 C10 -1.1(2) . . . . ?
C4 C5 C6 C7 1.3(3) . . . . ?
C4 C9 C10 C1 0.0(2) . . . . ?
C4 C9 C10 C11 179.88(15) . . . . ?
C5 C4 C9 C8 -0.7(2) . . . . ?
C5 C4 C9 C10 179.17(16) . . . . ?
C5 C6 C7 C8 -1.1(3) . . . . ?
C6 C7 C8 C9 0.0(2) . . . . ?
C6 C7 C8 C12 -179.06(18) . . . . ?
C7 C8 C9 C4 0.8(2) . . . . ?
C7 C8 C9 C10 -179.02(15) . . . . ?
C7 C8 C12 C11 178.89(19) . . . . ?
C7 C8 C12 C13 -0.2(3) . . . . ?
C8 C9 C10 C1 179.82(15) . . . . ?
C8 C9 C10 C11 -0.28(19) . . . . ?
C8 C12 C13 C14 179.27(16) . . . . ?
C8 C12 C13 C17 -0.3(3) . . . . ?
C9 C4 C5 C6 -0.4(3) . . . . ?
C9 C8 C12 C11 -0.28(18) . . . . ?
C9 C8 C12 C13 -179.36(17) . . . . ?
C9 C10 C11 C12 0.09(18) . . . . ?
C9 C10 C11 C16 178.63(17) . . . . ?
C10 C1 C2 C3 0.0(3) . . . . ?
C10 C11 C12 C8 0.12(18) . . . . ?
C10 C11 C12 C13 179.33(14) . . . . ?
C10 C11 C16 C15 -178.93(17) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
C11 C12 C13 C17 -179.31(15) . . . . ?
C12 C8 C9 C4 -179.81(15) . . . . ?
C12 C8 C9 C10 0.35(18) . . . . ?
C12 C11 C16 C15 -0.6(3) . . . . ?
C12 C13 C14 C15 -1.3(2) . . . . ?
C12 C13 C14 C20 179.79(15) . . . . ?
C12 C13 C17 C18 -179.00(16) . . . . ?
C13 C14 C15 C16 1.4(3) . . . . ?
C13 C14 C20 C19 -0.5(3) . . . . ?
C13 C17 C18 O2 178.61(16) . . . . ?
C13 C17 C18 C19 -1.1(3) . . . . ?
C14 C13 C17 C18 1.4(2) . . . . ?
C14 C15 C16 C11 -0.5(3) . . . . ?
C15 C14 C20 C19 -179.43(17) . . . . ?
C16 C11 C12 C8 -178.56(15) . . . . ?
C16 C11 C12 C13 0.6(2) . . . . ?
C17 C13 C14 C15 178.34(15) . . . . ?
C17 C13 C14 C20 -0.6(2) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C18 C19 C20 C14 0.8(3) . . . . ?
C20 C14 C15 C16 -179.70(17) . . . . ?
C21 O1 C1 C2 -9.0(2) . . . . ?
C21 O1 C1 C10 171.98(15) . . . . ?
C22 O2 C18 C17 6.1(3) . . . . ?
C22 O2 C18 C19 -174.11(17) . . . . ?

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1038631'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2015-02-04 downloaded from the CCDC.
;
_audit_creation_date             2014-12-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H16 O2'
_chemical_formula_sum            'C22 H16 O2'
_chemical_formula_weight         312.35
_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      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                   6.3011(13)
_cell_length_b                   15.399(3)
_cell_length_c                   16.736(3)
_cell_angle_alpha                104.22(3)
_cell_angle_beta                 94.76(3)
_cell_angle_gamma                96.35(3)
_cell_volume                     1554.3(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4823
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4717
_cell_measurement_theta_min      2.5483
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0753
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11770
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.199
_diffrn_reflns_theta_min         1.263
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             7038
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0621
_diffrn_orient_matrix_UB_12      0.1068
_diffrn_orient_matrix_UB_13      0.1102
_diffrn_orient_matrix_UB_21      0.0403
_diffrn_orient_matrix_UB_22      -0.0282
_diffrn_orient_matrix_UB_23      0.0464
_diffrn_orient_matrix_UB_31      0.0380
_diffrn_orient_matrix_UB_32      0.0336
_diffrn_orient_matrix_UB_33      -0.0358
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4155
_reflns_number_total             5567
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution    
;
'SHELXS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         5567
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0848
_refine_ls_restrained_S_all      1.177
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0306P)²+1.8216P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1539
_refine_ls_wR_factor_ref         0.1769
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C9(H9), C11(H11), C12(H12), C16(H16), C17(H17),
 C18(H18), C20(H20), C25(H25), C26(H26), C30(H30), C31(H31), C32(H32), C34(H34),
  C36(H36), C40(H40), C41(H41), C43(H43)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C44(H44A,H44B,H44C)
;
_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 1.6933(4) 0.49380(17) 0.63157(16) 0.0453(7) Uani 1 1 d . . . . .
O2 O 0.0877(4) 0.08387(17) 0.33198(16) 0.0406(6) Uani 1 1 d . . . . .
O3 O 2.3409(5) 0.8391(2) -0.11955(19) 0.0586(8) Uani 1 1 d . . . . .
O4 O 0.8719(4) 0.56816(18) 0.14003(16) 0.0457(7) Uani 1 1 d . . . . .
C1 C 1.8800(6) 0.5005(3) 0.6884(3) 0.0515(11) Uani 1 1 d . . . . .
H1A H 1.9707 0.4554 0.6642 0.077 Uiso 1 1 calc GR . . . .
H1B H 1.8366 0.4895 0.7403 0.077 Uiso 1 1 calc GR . . . .
H1C H 1.9610 0.5612 0.6997 0.077 Uiso 1 1 calc GR . . . .
C2 C 1.5519(6) 0.4145(2) 0.6152(2) 0.0364(9) Uani 1 1 d . . . . .
C3 C 1.3650(6) 0.4162(2) 0.5615(2) 0.0356(8) Uani 1 1 d . . . . .
H3 H 1.3497 0.4667 0.5394 0.043 Uiso 1 1 calc R . . . .
C4 C 1.2078(5) 0.3425(2) 0.5426(2) 0.0311(8) Uani 1 1 d . . . . .
C5 C 0.9953(5) 0.3194(2) 0.4931(2) 0.0310(8) Uani 1 1 d . . . . .
C6 C 0.8830(6) 0.3690(2) 0.4478(2) 0.0336(8) Uani 1 1 d . . . . .
H6 H 0.9465 0.4267 0.4443 0.040 Uiso 1 1 calc R . . . .
C7 C 0.6819(6) 0.3337(2) 0.4089(2) 0.0324(8) Uani 1 1 d . . . . .
H7 H 0.6050 0.3682 0.3796 0.039 Uiso 1 1 calc R . . . .
C8 C 0.5847(5) 0.2471(2) 0.4111(2) 0.0313(8) Uani 1 1 d . . . . .
C9 C 0.3763(5) 0.2114(2) 0.3692(2) 0.0325(8) Uani 1 1 d . . . . .
H9 H 0.2985 0.2465 0.3410 0.039 Uiso 1 1 calc R . . . .
C10 C 0.2871(5) 0.1257(2) 0.3697(2) 0.0320(8) Uani 1 1 d . . . . .
C11 C 0.4049(6) 0.0735(2) 0.4102(2) 0.0374(9) Uani 1 1 d . . . . .
H11 H 0.3452 0.0135 0.4081 0.045 Uiso 1 1 calc R . . . .
C12 C 0.6017(6) 0.1069(2) 0.4520(2) 0.0358(9) Uani 1 1 d . . . . .
H12 H 0.6751 0.0703 0.4799 0.043 Uiso 1 1 calc R . . . .
C13 C 0.7008(5) 0.1946(2) 0.4552(2) 0.0298(8) Uani 1 1 d . . . . .
C14 C 0.9050(5) 0.2335(2) 0.4974(2) 0.0295(8) Uani 1 1 d . . . . .
C15 C 1.0604(6) 0.1996(2) 0.5509(2) 0.0321(8) Uani 1 1 d . . . . .
C16 C 1.0669(6) 0.1248(3) 0.5814(2) 0.0394(9) Uani 1 1 d . . . . .
H16 H 0.9503 0.0770 0.5670 0.047 Uiso 1 1 calc R . . . .
C17 C 1.2509(6) 0.1195(3) 0.6350(2) 0.0417(9) Uani 1 1 d . . . . .
H17 H 1.2541 0.0676 0.6560 0.050 Uiso 1 1 calc R . . . .
C18 C 1.4246(6) 0.1871(3) 0.6574(2) 0.0435(10) Uani 1 1 d . . . . .
H18 H 1.5450 0.1812 0.6928 0.052 Uiso 1 1 calc R . . . .
C19 C 1.4219(5) 0.2659(2) 0.6271(2) 0.0337(8) Uani 1 1 d . . . . .
C20 C 1.5846(6) 0.3422(2) 0.6467(2) 0.0370(9) Uani 1 1 d . . . . .
H20 H 1.7132 0.3430 0.6809 0.044 Uiso 1 1 calc R . . . .
C21 C 1.2391(5) 0.2691(2) 0.5763(2) 0.0311(8) Uani 1 1 d . . . . .
C22 C -0.0308(6) 0.1300(3) 0.2820(2) 0.0447(10) Uani 1 1 d . . . . .
H22A H 0.0509 0.1390 0.2367 0.067 Uiso 1 1 calc GR . . . .
H22B H -0.0544 0.1888 0.3163 0.067 Uiso 1 1 calc GR . . . .
H22C H -0.1699 0.0935 0.2588 0.067 Uiso 1 1 calc GR . . . .
C23 C 2.4233(7) 0.7685(3) -0.1761(3) 0.0613(13) Uani 1 1 d . . . . .
H23A H 2.3166 0.7425 -0.2246 0.092 Uiso 1 1 calc GR . . . .
H23B H 2.4539 0.7213 -0.1485 0.092 Uiso 1 1 calc GR . . . .
H23C H 2.5559 0.7933 -0.1940 0.092 Uiso 1 1 calc GR . . . .
C24 C 2.1612(6) 0.8139(3) -0.0854(3) 0.0484(11) Uani 1 1 d . . . . .
C25 C 2.0957(7) 0.8868(3) -0.0264(3) 0.0533(11) Uani 1 1 d . . . . .
H25 H 2.1757 0.9455 -0.0142 0.064 Uiso 1 1 calc R . . . .
C26 C 1.9186(7) 0.8725(3) 0.0124(3) 0.0489(10) Uani 1 1 d . . . . .
H26 H 1.8754 0.9219 0.0510 0.059 Uiso 1 1 calc R . . . .
C27 C 1.7976(6) 0.7861(2) -0.0031(2) 0.0372(9) Uani 1 1 d . . . . .
C28 C 1.6125(6) 0.7668(2) 0.0356(2) 0.0366(9) Uani 1 1 d . . . . .
C29 C 1.4957(6) 0.8270(3) 0.0960(2) 0.0390(9) Uani 1 1 d . . . . .
C30 C 1.5127(7) 0.9168(3) 0.1344(2) 0.0470(10) Uani 1 1 d . . . . .
H30 H 1.6257 0.9582 0.1252 0.056 Uiso 1 1 calc R . . . .
C31 C 1.3585(7) 0.9478(3) 0.1885(2) 0.0488(10) Uani 1 1 d . . . . .
H31 H 1.3712 1.0106 0.2148 0.059 Uiso 1 1 calc R . . . .
C32 C 1.1909(6) 0.8908(3) 0.2047(2) 0.0456(10) Uani 1 1 d . . . . .
H32 H 1.0913 0.9141 0.2413 0.055 Uiso 1 1 calc R . . . .
C33 C 1.1708(6) 0.7960(3) 0.1652(2) 0.0370(9) Uani 1 1 d . . . . .
C34 C 1.0116(6) 0.7284(3) 0.1768(2) 0.0394(9) Uani 1 1 d . . . . .
H34 H 0.9063 0.7438 0.2134 0.047 Uiso 1 1 calc R . . . .
C35 C 1.0146(6) 0.6394(3) 0.1333(2) 0.0373(9) Uani 1 1 d . . . . .
C36 C 1.1667(6) 0.6132(3) 0.0774(2) 0.0383(9) Uani 1 1 d . . . . .
H36 H 1.1614 0.5519 0.0474 0.046 Uiso 1 1 calc R . . . .
C37 C 1.3211(6) 0.6779(2) 0.0676(2) 0.0333(8) Uani 1 1 d . . . . .
C38 C 1.3242(6) 0.7685(2) 0.1134(2) 0.0368(9) Uani 1 1 d . . . . .
C39 C 1.5049(6) 0.6791(3) 0.0189(2) 0.0379(9) Uani 1 1 d . . . . .
C40 C 1.5777(6) 0.6073(3) -0.0379(2) 0.0388(9) Uani 1 1 d . . . . .
H40 H 1.5033 0.5477 -0.0497 0.047 Uiso 1 1 calc R . . . .
C41 C 1.7560(6) 0.6247(3) -0.0754(2) 0.0410(9) Uani 1 1 d . . . . .
H41 H 1.8063 0.5763 -0.1127 0.049 Uiso 1 1 calc R . . . .
C42 C 1.8674(6) 0.7129(3) -0.0603(2) 0.0396(9) Uani 1 1 d . . . . .
C43 C 2.0520(6) 0.7296(3) -0.1004(2) 0.0428(10) Uani 1 1 d . . . . .
H43 H 2.0996 0.6810 -0.1384 0.051 Uiso 1 1 calc R . . . .
C44 C 0.7184(6) 0.5869(3) 0.1977(2) 0.0490(10) Uani 1 1 d . . . . .
H44A H 0.6253 0.6280 0.1812 0.073 Uiso 1 1 calc GR . . . .
H44B H 0.7933 0.6152 0.2532 0.073 Uiso 1 1 calc GR . . . .
H44C H 0.6308 0.5304 0.1981 0.073 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 1.428(4) . ?
O1 C2 1.383(4) . ?
O2 C10 1.372(4) . ?
O2 C22 1.438(4) . ?
O3 C23 1.431(5) . ?
O3 C24 1.371(5) . ?
O4 C35 1.372(4) . ?
O4 C44 1.425(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.427(5) . ?
C2 C20 1.372(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.375(5) . ?
C4 C5 1.474(5) . ?
C4 C21 1.407(5) . ?
C5 C6 1.405(5) . ?
C5 C14 1.403(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.365(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.415(5) . ?
C8 C9 1.420(5) . ?
C8 C13 1.438(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.378(5) . ?
C10 C11 1.404(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.353(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.411(5) . ?
C13 C14 1.408(5) . ?
C14 C15 1.493(5) . ?
C15 C16 1.373(5) . ?
C15 C21 1.423(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.428(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.426(5) . ?
C19 C20 1.424(5) . ?
C19 C21 1.387(5) . ?
C20 H20 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.425(6) . ?
C24 C43 1.354(6) . ?
C25 H25 0.9500 . ?
C25 C26 1.361(5) . ?
C26 H26 0.9500 . ?
C26 C27 1.412(5) . ?
C27 C28 1.418(5) . ?
C27 C42 1.425(5) . ?
C28 C29 1.496(5) . ?
C28 C39 1.393(5) . ?
C29 C30 1.363(5) . ?
C29 C38 1.424(5) . ?
C30 H30 0.9500 . ?
C30 C31 1.424(5) . ?
C31 H31 0.9500 . ?
C31 C32 1.385(6) . ?
C32 H32 0.9500 . ?
C32 C33 1.434(5) . ?
C33 C34 1.424(5) . ?
C33 C38 1.384(5) . ?
C34 H34 0.9500 . ?
C34 C35 1.388(5) . ?
C35 C36 1.416(5) . ?
C36 H36 0.9500 . ?
C36 C37 1.363(5) . ?
C37 C38 1.414(5) . ?
C37 C39 1.472(5) . ?
C39 C40 1.415(5) . ?
C40 H40 0.9500 . ?
C40 C41 1.365(5) . ?
C41 H41 0.9500 . ?
C41 C42 1.411(5) . ?
C42 C43 1.421(5) . ?
C43 H43 0.9500 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?

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 O1 C1 116.4(3) . . ?
C10 O2 C22 117.3(3) . . ?
C24 O3 C23 116.4(3) . . ?
C35 O4 C44 117.6(3) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 112.2(3) . . ?
C20 C2 O1 124.6(3) . . ?
C20 C2 C3 123.2(3) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 118.1(3) . . ?
C4 C3 H3 121.0 . . ?
C3 C4 C5 134.6(3) . . ?
C3 C4 C21 118.7(3) . . ?
C21 C4 C5 106.6(3) . . ?
C6 C5 C4 130.5(3) . . ?
C14 C5 C4 108.6(3) . . ?
C14 C5 C6 120.8(3) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.4(3) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 119.1 . . ?
C6 C7 C8 121.8(3) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 C9 120.7(3) . . ?
C7 C8 C13 119.3(3) . . ?
C9 C8 C13 120.1(3) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.9(3) . . ?
C10 C9 H9 120.1 . . ?
O2 C10 C9 125.4(3) . . ?
O2 C10 C11 114.9(3) . . ?
C9 C10 C11 119.7(3) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.4(3) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 119.1 . . ?
C11 C12 C13 121.8(3) . . ?
C13 C12 H12 119.1 . . ?
C12 C13 C8 117.1(3) . . ?
C14 C13 C8 118.2(3) . . ?
C14 C13 C12 124.7(3) . . ?
C5 C14 C13 120.5(3) . . ?
C5 C14 C15 107.9(3) . . ?
C13 C14 C15 131.6(3) . . ?
C16 C15 C14 137.0(3) . . ?
C16 C15 C21 117.3(3) . . ?
C21 C15 C14 105.7(3) . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.3(4) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 118.8 . . ?
C18 C17 C16 122.4(4) . . ?
C18 C17 H17 118.8 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.6(3) . . ?
C19 C18 H18 120.2 . . ?
C20 C19 C18 126.2(3) . . ?
C21 C19 C18 116.2(3) . . ?
C21 C19 C20 117.5(3) . . ?
C2 C20 C19 118.7(3) . . ?
C2 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C4 C21 C15 111.1(3) . . ?
C19 C21 C4 123.7(3) . . ?
C19 C21 C15 125.2(3) . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O3 C24 C25 113.1(4) . . ?
C43 C24 O3 126.9(4) . . ?
C43 C24 C25 120.0(4) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.0(4) . . ?
C26 C25 H25 120.0 . . ?
C25 C26 H26 119.2 . . ?
C25 C26 C27 121.6(4) . . ?
C27 C26 H26 119.2 . . ?
C26 C27 C28 124.3(3) . . ?
C26 C27 C42 118.1(4) . . ?
C28 C27 C42 117.5(3) . . ?
C27 C28 C29 131.1(3) . . ?
C39 C28 C27 121.0(3) . . ?
C39 C28 C29 107.8(3) . . ?
C30 C29 C28 137.2(4) . . ?
C30 C29 C38 117.6(3) . . ?
C38 C29 C28 105.2(3) . . ?
C29 C30 H30 120.5 . . ?
C29 C30 C31 119.0(4) . . ?
C31 C30 H30 120.5 . . ?
C30 C31 H31 118.4 . . ?
C32 C31 C30 123.2(4) . . ?
C32 C31 H31 118.4 . . ?
C31 C32 H32 120.7 . . ?
C31 C32 C33 118.6(4) . . ?
C33 C32 H32 120.7 . . ?
C34 C33 C32 125.6(3) . . ?
C38 C33 C32 116.4(4) . . ?
C38 C33 C34 117.9(3) . . ?
C33 C34 H34 120.9 . . ?
C35 C34 C33 118.2(3) . . ?
C35 C34 H34 120.9 . . ?
O4 C35 C34 123.7(3) . . ?
O4 C35 C36 113.3(3) . . ?
C34 C35 C36 123.0(4) . . ?
C35 C36 H36 120.7 . . ?
C37 C36 C35 118.6(3) . . ?
C37 C36 H36 120.7 . . ?
C36 C37 C38 119.1(3) . . ?
C36 C37 C39 135.5(3) . . ?
C38 C37 C39 105.3(3) . . ?
C33 C38 C29 125.1(3) . . ?
C33 C38 C37 123.0(4) . . ?
C37 C38 C29 111.8(3) . . ?
C28 C39 C37 109.8(3) . . ?
C28 C39 C40 120.4(3) . . ?
C40 C39 C37 129.7(3) . . ?
C39 C40 H40 120.4 . . ?
C41 C40 C39 119.3(4) . . ?
C41 C40 H40 120.4 . . ?
C40 C41 H41 119.2 . . ?
C40 C41 C42 121.6(3) . . ?
C42 C41 H41 119.2 . . ?
C41 C42 C27 120.1(3) . . ?
C41 C42 C43 120.7(3) . . ?
C43 C42 C27 119.2(4) . . ?
C24 C43 C42 121.0(4) . . ?
C24 C43 H43 119.5 . . ?
C42 C43 H43 119.5 . . ?
O4 C44 H44A 109.5 . . ?
O4 C44 H44B 109.5 . . ?
O4 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 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 C2 C3 C4 -177.8(3) . . . . ?
O1 C2 C20 C19 177.8(3) . . . . ?
O2 C10 C11 C12 -178.1(3) . . . . ?
O3 C24 C25 C26 179.5(4) . . . . ?
O3 C24 C43 C42 179.8(4) . . . . ?
O4 C35 C36 C37 -178.0(3) . . . . ?
C1 O1 C2 C3 176.7(3) . . . . ?
C1 O1 C2 C20 -3.0(5) . . . . ?
C2 C3 C4 C5 178.0(3) . . . . ?
C2 C3 C4 C21 -0.5(5) . . . . ?
C3 C2 C20 C19 -1.9(5) . . . . ?
C3 C4 C5 C6 -0.1(6) . . . . ?
C3 C4 C5 C14 -179.1(4) . . . . ?
C3 C4 C21 C15 179.5(3) . . . . ?
C3 C4 C21 C19 -0.8(5) . . . . ?
C4 C5 C6 C7 -177.6(3) . . . . ?
C4 C5 C14 C13 -179.8(3) . . . . ?
C4 C5 C14 C15 0.2(4) . . . . ?
C5 C4 C21 C15 0.5(4) . . . . ?
C5 C4 C21 C19 -179.8(3) . . . . ?
C5 C6 C7 C8 -1.7(5) . . . . ?
C5 C14 C15 C16 177.1(4) . . . . ?
C5 C14 C15 C21 0.1(4) . . . . ?
C6 C5 C14 C13 1.1(5) . . . . ?
C6 C5 C14 C15 -178.9(3) . . . . ?
C6 C7 C8 C9 -179.2(3) . . . . ?
C6 C7 C8 C13 -0.2(5) . . . . ?
C7 C8 C9 C10 177.8(3) . . . . ?
C7 C8 C13 C12 -176.8(3) . . . . ?
C7 C8 C13 C14 2.5(5) . . . . ?
C8 C9 C10 O2 179.7(3) . . . . ?
C8 C9 C10 C11 -1.3(5) . . . . ?
C8 C13 C14 C5 -2.9(5) . . . . ?
C8 C13 C14 C15 177.1(3) . . . . ?
C9 C8 C13 C12 2.1(5) . . . . ?
C9 C8 C13 C14 -178.6(3) . . . . ?
C9 C10 C11 C12 2.8(5) . . . . ?
C10 C11 C12 C13 -1.7(5) . . . . ?
C11 C12 C13 C8 -0.7(5) . . . . ?
C11 C12 C13 C14 -180.0(3) . . . . ?
C12 C13 C14 C5 176.4(3) . . . . ?
C12 C13 C14 C15 -3.7(6) . . . . ?
C13 C8 C9 C10 -1.1(5) . . . . ?
C13 C14 C15 C16 -2.8(7) . . . . ?
C13 C14 C15 C21 -179.9(3) . . . . ?
C14 C5 C6 C7 1.2(5) . . . . ?
C14 C15 C16 C17 -177.8(4) . . . . ?
C14 C15 C21 C4 -0.4(4) . . . . ?
C14 C15 C21 C19 179.9(3) . . . . ?
C15 C16 C17 C18 -0.2(6) . . . . ?
C16 C15 C21 C4 -178.1(3) . . . . ?
C16 C15 C21 C19 2.2(5) . . . . ?
C16 C17 C18 C19 0.5(6) . . . . ?
C17 C18 C19 C20 177.8(3) . . . . ?
C17 C18 C19 C21 0.4(5) . . . . ?
C18 C19 C20 C2 -176.9(3) . . . . ?
C18 C19 C21 C4 178.5(3) . . . . ?
C18 C19 C21 C15 -1.8(5) . . . . ?
C20 C2 C3 C4 1.9(5) . . . . ?
C20 C19 C21 C4 0.9(5) . . . . ?
C20 C19 C21 C15 -179.5(3) . . . . ?
C21 C4 C5 C6 178.6(3) . . . . ?
C21 C4 C5 C14 -0.4(4) . . . . ?
C21 C15 C16 C17 -1.1(5) . . . . ?
C21 C19 C20 C2 0.5(5) . . . . ?
C22 O2 C10 C9 5.7(5) . . . . ?
C22 O2 C10 C11 -173.4(3) . . . . ?
C23 O3 C24 C25 176.8(3) . . . . ?
C23 O3 C24 C43 -1.0(6) . . . . ?
C24 C25 C26 C27 1.0(6) . . . . ?
C25 C24 C43 C42 2.2(6) . . . . ?
C25 C26 C27 C28 179.7(4) . . . . ?
C25 C26 C27 C42 0.8(6) . . . . ?
C26 C27 C28 C29 2.6(6) . . . . ?
C26 C27 C28 C39 -178.1(4) . . . . ?
C26 C27 C42 C41 177.7(3) . . . . ?
C26 C27 C42 C43 -1.2(5) . . . . ?
C27 C28 C29 C30 1.6(7) . . . . ?
C27 C28 C29 C38 -179.1(4) . . . . ?
C27 C28 C39 C37 179.4(3) . . . . ?
C27 C28 C39 C40 -0.4(5) . . . . ?
C27 C42 C43 C24 -0.3(5) . . . . ?
C28 C27 C42 C41 -1.3(5) . . . . ?
C28 C27 C42 C43 179.9(3) . . . . ?
C28 C29 C30 C31 178.5(4) . . . . ?
C28 C29 C38 C33 -178.4(3) . . . . ?
C28 C29 C38 C37 -1.5(4) . . . . ?
C28 C39 C40 C41 0.6(5) . . . . ?
C29 C28 C39 C37 -1.2(4) . . . . ?
C29 C28 C39 C40 179.0(3) . . . . ?
C29 C30 C31 C32 0.3(6) . . . . ?
C30 C29 C38 C33 1.2(6) . . . . ?
C30 C29 C38 C37 178.1(3) . . . . ?
C30 C31 C32 C33 0.0(6) . . . . ?
C31 C32 C33 C34 178.3(4) . . . . ?
C31 C32 C33 C38 0.3(5) . . . . ?
C32 C33 C34 C35 179.7(3) . . . . ?
C32 C33 C38 C29 -0.9(5) . . . . ?
C32 C33 C38 C37 -177.5(3) . . . . ?
C33 C34 C35 O4 179.1(3) . . . . ?
C33 C34 C35 C36 -0.8(5) . . . . ?
C34 C33 C38 C29 -179.1(3) . . . . ?
C34 C33 C38 C37 4.4(5) . . . . ?
C34 C35 C36 C37 1.9(5) . . . . ?
C35 C36 C37 C38 0.1(5) . . . . ?
C35 C36 C37 C39 178.7(4) . . . . ?
C36 C37 C38 C29 179.8(3) . . . . ?
C36 C37 C38 C33 -3.3(5) . . . . ?
C36 C37 C39 C28 -178.4(4) . . . . ?
C36 C37 C39 C40 1.4(7) . . . . ?
C37 C39 C40 C41 -179.2(3) . . . . ?
C38 C29 C30 C31 -0.8(6) . . . . ?
C38 C33 C34 C35 -2.3(5) . . . . ?
C38 C37 C39 C28 0.3(4) . . . . ?
C38 C37 C39 C40 -179.9(4) . . . . ?
C39 C28 C29 C30 -177.8(5) . . . . ?
C39 C28 C29 C38 1.6(4) . . . . ?
C39 C37 C38 C29 0.8(4) . . . . ?
C39 C37 C38 C33 177.7(3) . . . . ?
C39 C40 C41 C42 -1.2(5) . . . . ?
C40 C41 C42 C27 1.5(5) . . . . ?
C40 C41 C42 C43 -179.6(3) . . . . ?
C41 C42 C43 C24 -179.2(4) . . . . ?
C42 C27 C28 C29 -178.5(3) . . . . ?
C42 C27 C28 C39 0.8(5) . . . . ?
C43 C24 C25 C26 -2.5(6) . . . . ?
C44 O4 C35 C34 -2.7(5) . . . . ?
C44 O4 C35 C36 177.2(3) . . . . ?

