# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1820140'
_audit_update_record             
;
2018-01-26 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H24 O2'
_chemical_formula_weight         392.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.5500(2)
_cell_length_b                   12.0209(2)
_cell_length_c                   25.0181(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.8280(10)
_cell_angle_gamma                90
_cell_volume                     4311.55(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4935
_cell_measurement_theta_min      4.7950
_cell_measurement_theta_max      69.9300

_exptl_crystal_description       bloc
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_F_000             1664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.583
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8185
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_av_R_equivalents  0.0118
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.586
_diffrn_reflns_theta_max         70.497
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4065
_reflns_number_gt                3715
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0538P)²+1.7447P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4065
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1125
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O2 O 0.12267(7) 0.70059(9) 0.47846(4) 0.0555(3) Uani 1 1 d . . . . .
O1 O 0.08932(8) 0.96134(9) 0.45259(4) 0.0586(3) Uani 1 1 d . . . . .
C28 C 0.04228(8) 0.79512(10) 0.37810(5) 0.0382(3) Uani 1 1 d . . . . .
C27 C -0.01331(8) 0.73888(10) 0.41549(5) 0.0386(3) Uani 1 1 d . . . . .
C26 C 0.10641(8) 0.74107(10) 0.35492(5) 0.0380(3) Uani 1 1 d . . . . .
C25 C -0.10948(9) 0.73436(11) 0.40149(6) 0.0469(3) Uani 1 1 d . . . . .
H25A H -0.137855 0.764624 0.368576 0.056 Uiso 1 1 calc R U . . .
C24 C 0.17157(8) 0.79808(11) 0.32394(5) 0.0405(3) Uani 1 1 d . . . . .
C23 C 0.01462(8) 0.91343(10) 0.36597(5) 0.0395(3) Uani 1 1 d . . . . .
C22 C 0.21290(9) 0.89939(12) 0.34102(6) 0.0489(3) Uani 1 1 d . . . . .
H22A H 0.198515 0.933347 0.371959 0.059 Uiso 1 1 calc R U . . .
C21 C -0.03749(10) 0.94313(12) 0.31650(6) 0.0498(3) Uani 1 1 d . . . . .
H21A H -0.050842 0.889686 0.289409 0.060 Uiso 1 1 calc R U . . .
C20 C 0.11527(9) 0.61761(10) 0.35905(5) 0.0399(3) Uani 1 1 d . . . . .
C19 C -0.12314(11) 0.64324(13) 0.48406(7) 0.0588(4) Uani 1 1 d . . . . .
H19A H -0.159766 0.611217 0.506974 0.071 Uiso 1 1 calc R U . . .
C18 C 0.19675(10) 0.74852(13) 0.27823(5) 0.0505(3) Uani 1 1 d . . . . .
H18A H 0.171374 0.679986 0.266440 0.061 Uiso 1 1 calc R U . . .
C17 C 0.02798(9) 0.69411(10) 0.46575(5) 0.0424(3) Uani 1 1 d . . . . .
C16 C 0.20057(10) 0.56711(12) 0.37696(6) 0.0506(3) Uani 1 1 d . . . . .
H16A H 0.253570 0.610672 0.386823 0.061 Uiso 1 1 calc R U . . .
C15 C -0.02754(10) 0.64714(12) 0.49973(6) 0.0517(3) Uani 1 1 d . . . . .
H15A H -0.000198 0.618205 0.533150 0.062 Uiso 1 1 calc R U . . .
C14 C 0.03863(10) 0.54959(12) 0.34337(7) 0.0555(4) Uani 1 1 d . . . . .
H14A H -0.019061 0.581515 0.330325 0.067 Uiso 1 1 calc R U . . .
C13 C 0.25901(11) 0.79993(15) 0.25015(6) 0.0609(4) Uani 1 1 d . . . . .
H13A H 0.274683 0.765864 0.219559 0.073 Uiso 1 1 calc R U . . .
C12 C 0.03511(9) 0.99585(11) 0.40570(5) 0.0447(3) Uani 1 1 d . . . . .
C11 C 0.00281(11) 1.10384(12) 0.39551(7) 0.0587(4) Uani 1 1 d . . . . .
H11A H 0.017128 1.158472 0.421938 0.070 Uiso 1 1 calc R U . . .
C10 C 0.29790(11) 0.90078(16) 0.26699(7) 0.0649(4) Uani 1 1 d . . . . .
H10A H 0.339265 0.935336 0.247764 0.078 Uiso 1 1 calc R U . . .
C9 C -0.16468(10) 0.68608(13) 0.43508(7) 0.0572(4) Uani 1 1 d . . . . .
H9A H -0.229083 0.682768 0.424543 0.069 Uiso 1 1 calc R U . . .
C8 C -0.07026(13) 1.05064(14) 0.30636(7) 0.0669(4) Uani 1 1 d . . . . .
H8A H -0.105342 1.069020 0.272882 0.080 Uiso 1 1 calc R U . . .
C7 C 0.04629(13) 0.43503(13) 0.34673(8) 0.0678(5) Uani 1 1 d . . . . .
H7A H -0.006136 0.390850 0.336165 0.081 Uiso 1 1 calc R U . . .
C6 C 0.27504(11) 0.95029(15) 0.31266(7) 0.0617(4) Uani 1 1 d . . . . .
H6A H 0.301537 1.018271 0.324478 0.074 Uiso 1 1 calc R U . . .
C5 C 0.20761(13) 0.45228(13) 0.38029(6) 0.0616(4) Uani 1 1 d . . . . .
H5A H 0.265236 0.419565 0.392673 0.074 Uiso 1 1 calc R U . . .
C4 C -0.05040(12) 1.12970(13) 0.34622(8) 0.0681(5) Uani 1 1 d . . . . .
H4A H -0.073201 1.201616 0.339828 0.082 Uiso 1 1 calc R U . . .
C3 C 0.16597(12) 0.66834(16) 0.53130(7) 0.0674(4) Uani 1 1 d . . . . .
H3A H 0.232305 0.676984 0.534723 0.101 Uiso 1 1 calc R U . . .
H3B H 0.143383 0.714283 0.557657 0.101 Uiso 1 1 calc R U . . .
H3C H 0.151521 0.591911 0.537312 0.101 Uiso 1 1 calc R U . . .
C2 C 0.11898(13) 1.04159(16) 0.49341(7) 0.0718(5) Uani 1 1 d . . . . .
H2A H 0.156396 1.006107 0.523995 0.108 Uiso 1 1 calc R U . . .
H2B H 0.155181 1.097809 0.479327 0.108 Uiso 1 1 calc R U . . .
H2C H 0.065458 1.075207 0.504553 0.108 Uiso 1 1 calc R U . . .
C1 C 0.13059(14) 0.38639(13) 0.36554(7) 0.0631(4) Uani 1 1 d . . . . .
H1A H 0.135601 0.309401 0.368280 0.076 Uiso 1 1 calc R U . . .


_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
O2 C17 1.3623(16) . ?
O2 C3 1.4181(17) . ?
O1 C12 1.3619(17) . ?
O1 C2 1.4175(18) . ?
C28 C26 1.3469(17) . ?
C28 C23 1.4950(17) . ?
C28 C27 1.4983(16) . ?
C27 C25 1.3843(18) . ?
C27 C17 1.4047(18) . ?
C26 C24 1.4899(17) . ?
C26 C20 1.4918(17) . ?
C25 C9 1.385(2) . ?
C24 C22 1.3928(19) . ?
C24 C18 1.3927(18) . ?
C23 C21 1.3834(18) . ?
C23 C12 1.3989(18) . ?
C22 C6 1.383(2) . ?
C21 C8 1.386(2) . ?
C20 C14 1.3844(19) . ?
C20 C16 1.3855(18) . ?
C19 C9 1.371(2) . ?
C19 C15 1.380(2) . ?
C18 C13 1.383(2) . ?
C17 C15 1.3887(19) . ?
C16 C5 1.386(2) . ?
C14 C7 1.383(2) . ?
C13 C10 1.373(2) . ?
C12 C11 1.389(2) . ?
C11 C4 1.375(2) . ?
C10 C6 1.379(2) . ?
C8 C4 1.372(3) . ?
C7 C1 1.368(3) . ?
C5 C1 1.370(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
C17 O2 C3 118.21(12) . . ?
C12 O1 C2 118.27(13) . . ?
C26 C28 C23 123.63(11) . . ?
C26 C28 C27 122.59(11) . . ?
C23 C28 C27 113.62(10) . . ?
C25 C27 C17 118.09(11) . . ?
C25 C27 C28 119.33(11) . . ?
C17 C27 C28 122.53(11) . . ?
C28 C26 C24 123.45(11) . . ?
C28 C26 C20 120.54(11) . . ?
C24 C26 C20 116.01(10) . . ?
C9 C25 C27 121.92(13) . . ?
C22 C24 C18 117.75(12) . . ?
C22 C24 C26 121.49(11) . . ?
C18 C24 C26 120.68(12) . . ?
C21 C23 C12 118.08(12) . . ?
C21 C23 C28 120.96(11) . . ?
C12 C23 C28 120.82(11) . . ?
C6 C22 C24 121.01(14) . . ?
C23 C21 C8 121.55(14) . . ?
C14 C20 C16 117.81(13) . . ?
C14 C20 C26 120.80(12) . . ?
C16 C20 C26 121.35(12) . . ?
C9 C19 C15 120.68(13) . . ?
C13 C18 C24 120.85(14) . . ?
O2 C17 C15 123.44(12) . . ?
O2 C17 C27 116.61(11) . . ?
C15 C17 C27 119.94(12) . . ?
C20 C16 C5 120.59(14) . . ?
C19 C15 C17 120.23(13) . . ?
C7 C14 C20 121.21(15) . . ?
C10 C13 C18 120.65(14) . . ?
O1 C12 C11 124.80(13) . . ?
O1 C12 C23 114.72(12) . . ?
C11 C12 C23 120.46(13) . . ?
C4 C11 C12 119.79(14) . . ?
C13 C10 C6 119.36(14) . . ?
C19 C9 C25 119.14(14) . . ?
C4 C8 C21 119.32(15) . . ?
C1 C7 C14 120.31(16) . . ?
C10 C6 C22 120.36(16) . . ?
C1 C5 C16 120.72(15) . . ?
C8 C4 C11 120.78(15) . . ?
C7 C1 C5 119.32(14) . . ?

_refine_diff_density_max         0.162
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1820143'
_audit_update_record             
;
2018-01-26 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H24 O2'
_chemical_formula_weight         404.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.1335(4)
_cell_length_b                   9.1220(2)
_cell_length_c                   17.8477(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.798(3)
_cell_angle_gamma                90.00
_cell_volume                     2165.02(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4318
_cell_measurement_theta_min      5.1870
_cell_measurement_theta_max      70.5660

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7880
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         70.75
_reflns_number_total             4047
_reflns_number_gt                3482
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0638P)²+1.0930P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4047
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.1249
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.70921(8) 0.67088(13) 1.01023(7) 0.0306(3) Uani 1 1 d . . .
O2 O 0.61329(9) 0.92550(14) 1.02546(7) 0.0330(3) Uani 1 1 d . . .
C14 C 0.80025(11) 0.92991(17) 0.99681(9) 0.0229(3) Uani 1 1 d . . .
C15 C 0.86041(11) 0.79426(18) 1.02734(9) 0.0235(3) Uani 1 1 d . . .
C21 C 0.77945(12) 1.02106(17) 1.05947(9) 0.0254(3) Uani 1 1 d . . .
C4 C 0.79416(12) 0.87617(18) 0.85925(9) 0.0258(3) Uani 1 1 d . . .
C7 C 0.70823(11) 1.10125(17) 0.88625(9) 0.0237(3) Uani 1 1 d . . .
C23 C 0.83969(16) 1.1973(2) 1.16787(11) 0.0371(4) Uani 1 1 d . . .
H23A H 0.8916 1.2543 1.2010 0.044 Uiso 1 1 calc R . .
C19 C 0.86616(13) 0.53997(19) 1.06965(10) 0.0301(4) Uani 1 1 d . . .
H19A H 0.8327 0.4553 1.0755 0.036 Uiso 1 1 calc R . .
C5 C 0.85236(13) 0.9339(2) 0.81727(10) 0.0345(4) Uani 1 1 d . . .
H5A H 0.8743 1.0306 0.8254 0.041 Uiso 1 1 calc R . .
C22 C 0.85543(14) 1.11017(18) 1.10881(10) 0.0301(4) Uani 1 1 d . . .
H22A H 0.9179 1.1116 1.1022 0.036 Uiso 1 1 calc R . .
C26 C 0.68636(13) 1.01712(18) 1.07183(10) 0.0286(4) Uani 1 1 d . . .
C13 C 0.76931(11) 0.96928(17) 0.91955(9) 0.0227(3) Uani 1 1 d . . .
C16 C 0.96582(12) 0.79258(19) 1.04986(10) 0.0300(4) Uani 1 1 d . . .
H16A H 0.9996 0.8760 1.0426 0.036 Uiso 1 1 calc R . .
C20 C 0.81187(12) 0.66577(18) 1.03780(9) 0.0253(3) Uani 1 1 d . . .
C12 C 0.73002(13) 1.23985(18) 0.92060(10) 0.0283(4) Uani 1 1 d . . .
H12A H 0.7853 1.2516 0.9668 0.034 Uiso 1 1 calc R . .
C3 C 0.75917(15) 0.7320(2) 0.84457(11) 0.0364(4) Uani 1 1 d . . .
H3A H 0.7189 0.6933 0.8715 0.044 Uiso 1 1 calc R . .
C17 C 1.02033(14) 0.6665(2) 1.08305(11) 0.0363(4) Uani 1 1 d . . .
H17A H 1.0901 0.6668 1.0987 0.044 Uiso 1 1 calc R . .
C25 C 0.66947(15) 1.1084(2) 1.12888(11) 0.0365(4) Uani 1 1 d . . .
H25A H 0.6066 1.1092 1.1349 0.044 Uiso 1 1 calc R . .
C11 C 0.67140(15) 1.3600(2) 0.88761(11) 0.0366(4) Uani 1 1 d . . .
H11A H 0.6873 1.4511 0.9120 0.044 Uiso 1 1 calc R . .
C24 C 0.74517(16) 1.1976(2) 1.17652(11) 0.0390(4) Uani 1 1 d . . .
H24A H 0.7331 1.2578 1.2143 0.047 Uiso 1 1 calc R . .
C18 C 0.97005(14) 0.5407(2) 1.09267(11) 0.0348(4) Uani 1 1 d . . .
H18A H 1.0063 0.4569 1.1146 0.042 Uiso 1 1 calc R . .
C8 C 0.62538(13) 1.0884(2) 0.81592(11) 0.0337(4) Uani 1 1 d . . .
H8A H 0.6101 0.9978 0.7909 0.040 Uiso 1 1 calc R . .
C29 C 0.65695(13) 0.6026(2) 1.05790(12) 0.0366(4) Uani 1 1 d . . .
H29A H 0.6947 0.6145 1.1141 0.044 Uiso 1 1 calc R . .
H29B H 0.6479 0.4987 1.0461 0.044 Uiso 1 1 calc R . .
C27 C 0.56364(14) 0.8346(2) 1.06847(13) 0.0395(5) Uani 1 1 d . . .
H27A H 0.4970 0.8727 1.0610 0.047 Uiso 1 1 calc R . .
H27B H 0.6020 0.8357 1.1250 0.047 Uiso 1 1 calc R . .
C6 C 0.87788(16) 0.8458(3) 0.76253(11) 0.0487(6) Uani 1 1 d . . .
H6A H 0.9179 0.8833 0.7350 0.058 Uiso 1 1 calc R . .
C10 C 0.58944(15) 1.3464(2) 0.81879(12) 0.0414(5) Uani 1 1 d . . .
H10A H 0.5503 1.4275 0.7963 0.050 Uiso 1 1 calc R . .
C9 C 0.56633(14) 1.2076(2) 0.78332(13) 0.0417(5) Uani 1 1 d . . .
H9A H 0.5106 1.1963 0.7374 0.050 Uiso 1 1 calc R . .
C28 C 0.55610(13) 0.6785(2) 1.03673(13) 0.0407(5) Uani 1 1 d . . .
H28A H 0.5128 0.6221 1.0580 0.049 Uiso 1 1 calc R . .
H28B H 0.5250 0.6806 0.9792 0.049 Uiso 1 1 calc R . .
C2 C 0.78437(17) 0.6469(2) 0.79015(11) 0.0482(5) Uani 1 1 d . . .
H2A H 0.7612 0.5509 0.7809 0.058 Uiso 1 1 calc R . .
C1 C 0.84316(18) 0.7028(3) 0.74968(12) 0.0526(6) Uani 1 1 d . . .
H1A H 0.8599 0.6443 0.7133 0.063 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C20 1.3660(19) . ?
O1 C29 1.443(2) . ?
O2 C26 1.368(2) . ?
O2 C27 1.461(2) . ?
C14 C13 1.347(2) . ?
C14 C15 1.496(2) . ?
C14 C21 1.500(2) . ?
C15 C20 1.402(2) . ?
C15 C16 1.406(2) . ?
C21 C22 1.396(2) . ?
C21 C26 1.406(2) . ?
C4 C5 1.390(2) . ?
C4 C3 1.398(2) . ?
C4 C13 1.503(2) . ?
C7 C12 1.393(2) . ?
C7 C8 1.402(2) . ?
C7 C13 1.483(2) . ?
C23 C24 1.396(3) . ?
C23 C22 1.397(2) . ?
C19 C18 1.384(2) . ?
C19 C20 1.390(2) . ?
C5 C6 1.403(3) . ?
C26 C25 1.397(2) . ?
C16 C17 1.400(2) . ?
C12 C11 1.380(2) . ?
C3 C2 1.381(3) . ?
C17 C18 1.390(3) . ?
C25 C24 1.383(3) . ?
C11 C10 1.379(3) . ?
C8 C9 1.374(3) . ?
C29 C28 1.513(3) . ?
C27 C28 1.522(3) . ?
C6 C1 1.386(4) . ?
C10 C9 1.403(3) . ?
C2 C1 1.371(4) . ?

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 O1 C29 117.79(13) . . ?
C26 O2 C27 115.31(14) . . ?
C13 C14 C15 122.76(14) . . ?
C13 C14 C21 122.54(14) . . ?
C15 C14 C21 114.69(13) . . ?
C20 C15 C16 118.15(15) . . ?
C20 C15 C14 119.78(14) . . ?
C16 C15 C14 122.00(14) . . ?
C22 C21 C26 118.46(15) . . ?
C22 C21 C14 119.33(14) . . ?
C26 C21 C14 122.19(15) . . ?
C5 C4 C3 119.45(17) . . ?
C5 C4 C13 119.75(15) . . ?
C3 C4 C13 120.80(16) . . ?
C12 C7 C8 117.57(15) . . ?
C12 C7 C13 123.25(14) . . ?
C8 C7 C13 119.17(14) . . ?
C24 C23 C22 119.20(18) . . ?
C18 C19 C20 120.01(16) . . ?
C4 C5 C6 119.8(2) . . ?
C21 C22 C23 121.48(17) . . ?
O2 C26 C25 121.66(16) . . ?
O2 C26 C21 118.39(15) . . ?
C25 C26 C21 119.93(17) . . ?
C14 C13 C7 124.74(14) . . ?
C14 C13 C4 120.59(14) . . ?
C7 C13 C4 114.66(13) . . ?
C17 C16 C15 120.54(16) . . ?
O1 C20 C19 123.17(15) . . ?
O1 C20 C15 115.56(14) . . ?
C19 C20 C15 121.14(15) . . ?
C11 C12 C7 121.44(16) . . ?
C2 C3 C4 120.1(2) . . ?
C18 C17 C16 119.95(16) . . ?
C24 C25 C26 120.73(18) . . ?
C10 C11 C12 120.69(18) . . ?
C25 C24 C23 120.05(17) . . ?
C19 C18 C17 120.18(16) . . ?
C9 C8 C7 121.10(17) . . ?
O1 C29 C28 106.40(15) . . ?
O2 C27 C28 108.71(15) . . ?
C1 C6 C5 119.6(2) . . ?
C11 C10 C9 118.68(18) . . ?
C8 C9 C10 120.49(18) . . ?
C29 C28 C27 113.19(16) . . ?
C1 C2 C3 120.6(2) . . ?
C2 C1 C6 120.45(19) . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        70.75
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.046

# 
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag 
# 
#data_1 
_shelx_title                     ' 1 in P2(1)/c'
_shelx_refln_list_code           4
_shelx_F_calc_maximum            169.31
#_exptl_crystal_F_000       856.00 
_reflns_d_resolution_high        0.8165

#loop_ 
# _symmetry_equiv_pos_as_xyz 
# 'x, y, z' 
# '-x, y+1/2, -z+1/2' 
# '-x, -y, -z' 
# 'x, -y-1/2, z-1/2' 
# 
#_cell_length_a    14.1335 
#_cell_length_b     9.1220 
#_cell_length_c    17.8477 
#_cell_angle_alpha  90.000 
#_cell_angle_beta  109.798 
#_cell_angle_gamma  90.000 
# 
_shelx_F_squared_multiplier      1.000
####################################################################### 
# 
# 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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1820141'
_audit_update_record             
;
2018-01-26 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H20 O2'
_chemical_formula_weight         376.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   9.2661(2)
_cell_length_b                   8.4682(2)
_cell_length_c                   25.0320(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.682(2)
_cell_angle_gamma                90
_cell_volume                     1946.56(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4723
_cell_measurement_theta_min      4.8090
_cell_measurement_theta_max      70.4660


_exptl_crystal_description       bloc
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.626
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7106
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0136
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.563
_diffrn_reflns_theta_max         70.501
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3646
_reflns_number_gt                3384
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0461P)²+0.6056P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3646
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0975
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
O2 O 0.35379(9) -0.05713(10) 0.24929(3) 0.0287(2) Uani 1 1 d . . . . .
O1 O 0.13307(9) -0.01478(11) 0.28169(3) 0.0291(2) Uani 1 1 d . . . . .
C27 C 0.29545(12) -0.09159(14) 0.36344(5) 0.0230(2) Uani 1 1 d . . . . .
C26 C 0.39863(12) 0.04473(14) 0.36279(5) 0.0234(2) Uani 1 1 d . . . . .
C25 C 0.48286(12) 0.31400(14) 0.39483(5) 0.0239(2) Uani 1 1 d . . . . .
C24 C 0.17220(12) -0.11295(14) 0.32552(5) 0.0238(2) Uani 1 1 d . . . . .
C23 C 0.32304(14) -0.20361(15) 0.40448(5) 0.0285(3) Uani 1 1 d . . . . .
H23A H 0.4070 -0.1944 0.4292 0.034 Uiso 1 1 calc R U . . .
C22 C 0.07700(13) -0.23717(15) 0.33047(5) 0.0283(3) Uani 1 1 d . . . . .
H22A H -0.0054 -0.2494 0.3052 0.034 Uiso 1 1 calc R U . . .
C21 C 0.66438(14) 0.03987(16) 0.35218(6) 0.0317(3) Uani 1 1 d . . . . .
H21A H 0.6849 0.0778 0.3872 0.038 Uiso 1 1 calc R U . . .
C20 C 0.38584(12) 0.17213(14) 0.39371(4) 0.0235(2) Uani 1 1 d . . . . .
C19 C 0.26061(13) 0.18529(14) 0.42590(5) 0.0248(3) Uani 1 1 d . . . . .
C18 C 0.24553(13) 0.05598(15) 0.25675(5) 0.0268(3) Uani 1 1 d . . . . .
C17 C 0.51914(13) 0.01978(14) 0.32964(5) 0.0253(3) Uani 1 1 d . . . . .
C16 C 0.49952(14) 0.39450(15) 0.34763(5) 0.0299(3) Uani 1 1 d . . . . .
H16A H 0.4515 0.3584 0.3149 0.036 Uiso 1 1 calc R U . . .
C15 C 0.66139(14) 0.58083(16) 0.39684(5) 0.0330(3) Uani 1 1 d . . . . .
H15A H 0.7216 0.6689 0.3975 0.040 Uiso 1 1 calc R U . . .
C14 C 0.22882(15) -0.32782(16) 0.40943(5) 0.0334(3) Uani 1 1 d . . . . .
H14A H 0.2491 -0.4008 0.4372 0.040 Uiso 1 1 calc R U . . .
C13 C 0.49240(13) -0.03427(14) 0.27646(5) 0.0265(3) Uani 1 1 d . . . . .
C12 C 0.10398(14) -0.34238(15) 0.37266(5) 0.0321(3) Uani 1 1 d . . . . .
H12A H 0.0382 -0.4233 0.3764 0.039 Uiso 1 1 calc R U . . .
C11 C 0.58683(15) 0.52816(16) 0.34863(5) 0.0336(3) Uani 1 1 d . . . . .
H11A H 0.5951 0.5822 0.3168 0.040 Uiso 1 1 calc R U . . .
C10 C 0.55567(14) 0.37101(16) 0.44319(5) 0.0322(3) Uani 1 1 d . . . . .
H10A H 0.5437 0.3208 0.4753 0.039 Uiso 1 1 calc R U . . .
C9 C 0.26795(15) 0.13012(17) 0.47867(5) 0.0339(3) Uani 1 1 d . . . . .
H9A H 0.3529 0.0828 0.4953 0.041 Uiso 1 1 calc R U . . .
C8 C 0.14876(17) 0.14572(18) 0.50653(6) 0.0423(4) Uani 1 1 d . . . . .
H8A H 0.1542 0.1082 0.5416 0.051 Uiso 1 1 calc R U . . .
C7 C 0.77810(14) 0.00479(18) 0.32373(6) 0.0396(3) Uani 1 1 d . . . . .
H7A H 0.8739 0.0203 0.3394 0.048 Uiso 1 1 calc R U . . .
C6 C 0.64595(15) 0.50187(17) 0.44400(5) 0.0361(3) Uani 1 1 d . . . . .
H6A H 0.6964 0.5366 0.4765 0.043 Uiso 1 1 calc R U . . .
C5 C 0.60632(15) -0.07249(18) 0.24800(5) 0.0363(3) Uani 1 1 d . . . . .
H5A H 0.5868 -0.1108 0.2130 0.044 Uiso 1 1 calc R U . . .
C4 C 0.13264(14) 0.25473(16) 0.40210(6) 0.0355(3) Uani 1 1 d . . . . .
H4A H 0.1260 0.2914 0.3668 0.043 Uiso 1 1 calc R U . . .
C3 C 0.74849(15) -0.0536(2) 0.27174(6) 0.0426(4) Uani 1 1 d . . . . .
H3A H 0.8247 -0.0803 0.2528 0.051 Uiso 1 1 calc R U . . .
C2 C 0.02290(17) 0.21617(17) 0.48263(7) 0.0451(4) Uani 1 1 d . . . . .
H2A H -0.0561 0.2274 0.5017 0.054 Uiso 1 1 calc R U . . .
C1 C 0.01400(16) 0.27020(18) 0.43027(7) 0.0460(4) Uani 1 1 d . . . . .
H1A H -0.0714 0.3170 0.4139 0.055 Uiso 1 1 calc R U . . .
H18A H 0.2907(14) 0.1464(17) 0.2778(5) 0.023(3) Uiso 1 1 d . . . . .
H18B H 0.1986(15) 0.0902(17) 0.2211(6) 0.026(3) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C13 1.3842(15) . ?
O2 C18 1.4173(15) . ?
O1 C24 1.3856(14) . ?
O1 C18 1.4173(15) . ?
C27 C24 1.3957(17) . ?
C27 C23 1.3965(17) . ?
C27 C26 1.5004(16) . ?
C26 C20 1.3423(17) . ?
C26 C17 1.4926(15) . ?
C25 C16 1.3904(17) . ?
C25 C10 1.3911(17) . ?
C25 C20 1.4985(16) . ?
C24 C22 1.3890(17) . ?
C23 C14 1.3830(18) . ?
C22 C12 1.3789(18) . ?
C21 C7 1.3807(18) . ?
C21 C17 1.3984(17) . ?
C20 C19 1.5027(15) . ?
C19 C4 1.3849(18) . ?
C19 C9 1.3942(17) . ?
C17 C13 1.3981(17) . ?
C16 C11 1.3895(19) . ?
C15 C6 1.3807(19) . ?
C15 C11 1.3819(19) . ?
C14 C12 1.3840(19) . ?
C13 C5 1.3884(17) . ?
C10 C6 1.3871(19) . ?
C9 C8 1.3890(19) . ?
C8 C2 1.374(2) . ?
C7 C3 1.385(2) . ?
C5 C3 1.380(2) . ?
C4 C1 1.3894(19) . ?
C2 C1 1.380(2) . ?

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
C13 O2 C18 117.86(9) . . ?
C24 O1 C18 118.20(9) . . ?
C24 C27 C23 117.70(11) . . ?
C24 C27 C26 123.85(11) . . ?
C23 C27 C26 118.45(10) . . ?
C20 C26 C17 124.38(11) . . ?
C20 C26 C27 120.44(10) . . ?
C17 C26 C27 114.98(10) . . ?
C16 C25 C10 118.25(11) . . ?
C16 C25 C20 120.77(11) . . ?
C10 C25 C20 120.96(11) . . ?
O1 C24 C22 115.02(10) . . ?
O1 C24 C27 124.36(11) . . ?
C22 C24 C27 120.61(11) . . ?
C14 C23 C27 121.79(12) . . ?
C12 C22 C24 120.35(11) . . ?
C7 C21 C17 121.70(13) . . ?
C26 C20 C25 123.79(10) . . ?
C26 C20 C19 120.19(10) . . ?
C25 C20 C19 115.77(10) . . ?
C4 C19 C9 118.71(12) . . ?
C4 C19 C20 118.62(11) . . ?
C9 C19 C20 122.67(11) . . ?
O1 C18 O2 110.33(10) . . ?
C13 C17 C21 117.55(11) . . ?
C13 C17 C26 121.68(11) . . ?
C21 C17 C26 120.64(11) . . ?
C11 C16 C25 120.97(12) . . ?
C6 C15 C11 119.57(12) . . ?
C23 C14 C12 119.32(12) . . ?
O2 C13 C5 115.75(11) . . ?
O2 C13 C17 123.25(10) . . ?
C5 C13 C17 120.98(12) . . ?
C22 C12 C14 120.10(12) . . ?
C15 C11 C16 120.03(12) . . ?
C6 C10 C25 120.75(12) . . ?
C8 C9 C19 120.16(13) . . ?
C2 C8 C9 120.56(14) . . ?
C21 C7 C3 119.50(13) . . ?
C15 C6 C10 120.38(12) . . ?
C3 C5 C13 119.96(13) . . ?
C19 C4 C1 120.78(13) . . ?
C5 C3 C7 120.26(12) . . ?
C8 C2 C1 119.79(13) . . ?
C2 C1 C4 119.99(14) . . ?

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_1_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1820142'
_audit_update_record             
;
2018-01-26 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H22 O2'
_chemical_formula_weight         390.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

loop_
_symmetry_equiv_pos_as_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                   9.1319(3)
_cell_length_b                   19.4605(5)
_cell_length_c                   12.3122(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.242(3)
_cell_angle_gamma                90.00
_cell_volume                     2170.56(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4731
_cell_measurement_theta_min      4.2590
_cell_measurement_theta_max      70.5790

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.579
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8212
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.27
_diffrn_reflns_theta_max         70.71
_reflns_number_total             4065
_reflns_number_gt                3464
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4065
_refine_ls_number_parameters     272
_refine_ls_number_restraints     762
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.2440
_refine_ls_wR_factor_gt          0.2326
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O -0.22929(13) 0.16728(7) 0.68124(11) 0.0283(4) Uani 1 1 d . . .
O1 O -0.07512(13) 0.29911(6) 0.74890(11) 0.0277(4) Uani 1 1 d . . .
C28 C 0.14831(18) 0.23435(9) 0.80457(13) 0.0216(4) Uani 1 1 d U . .
C27 C 0.06535(17) 0.16849(9) 0.79193(14) 0.0210(4) Uani 1 1 d U . .
C26 C -0.0529(2) 0.16252(9) 0.96496(15) 0.0268(4) Uani 1 1 d U . .
H26A H 0.0411 0.1632 1.0041 0.032 Uiso 1 1 calc R . .
C25 C 0.2600(2) 0.16259(9) 0.59665(15) 0.0266(4) Uani 1 1 d U . .
H25A H 0.1971 0.2003 0.5860 0.032 Uiso 1 1 calc R . .
C24 C 0.32966(19) 0.05561(9) 0.68609(15) 0.0255(4) Uani 1 1 d U . .
H24A H 0.3124 0.0207 0.7344 0.031 Uiso 1 1 calc R . .
C23 C 0.07605(18) 0.29695(9) 0.78238(14) 0.0229(4) Uani 1 1 d U . .
C22 C 0.1498(2) 0.35883(10) 0.79916(16) 0.0289(4) Uani 1 1 d U . .
H22A H 0.0985 0.3999 0.7859 0.035 Uiso 1 1 calc R . .
C21 C -0.3331(2) 0.16041(10) 0.84913(19) 0.0332(5) Uani 1 1 d U . .
H21A H -0.4270 0.1592 0.8099 0.040 Uiso 1 1 calc R . .
C20 C 0.10354(17) 0.11363(8) 0.73461(13) 0.0203(4) Uani 1 1 d U . .
C19 C -0.1527(2) -0.02595(11) 0.61281(17) 0.0324(4) Uani 1 1 d U . .
H19A H -0.2005 -0.0377 0.5441 0.039 Uiso 1 1 calc R . .
C18 C -0.21081(19) 0.16496(9) 0.79413(16) 0.0246(4) Uani 1 1 d U . .
C17 C 0.23322(17) 0.11136(8) 0.67200(14) 0.0215(4) Uani 1 1 d U . .
C16 C -0.06837(18) 0.16523(8) 0.85051(14) 0.0218(4) Uani 1 1 d U . .
C15 C -0.05971(19) 0.03068(9) 0.62471(15) 0.0257(4) Uani 1 1 d U . .
H15A H -0.0451 0.0562 0.5632 0.031 Uiso 1 1 calc R . .
C14 C 0.29880(19) 0.23584(10) 0.84197(15) 0.0263(4) Uani 1 1 d U . .
H14A H 0.3494 0.1948 0.8571 0.032 Uiso 1 1 calc R . .
C13 C 0.01210(17) 0.05015(9) 0.72630(14) 0.0217(4) Uani 1 1 d U . .
C12 C 0.3748(2) 0.29800(10) 0.85702(16) 0.0297(4) Uani 1 1 d U . .
H12A H 0.4754 0.2981 0.8813 0.036 Uiso 1 1 calc R . .
C11 C -0.3167(2) 0.15756(11) 0.96185(19) 0.0357(5) Uani 1 1 d U . .
H11A H -0.3995 0.1548 0.9986 0.043 Uiso 1 1 calc R . .
C10 C -0.1751(2) 0.15879(10) 1.02120(17) 0.0341(5) Uani 1 1 d U . .
H10A H -0.1633 0.1571 1.0973 0.041 Uiso 1 1 calc R . .
C9 C 0.3805(2) 0.15726(10) 0.53768(16) 0.0309(4) Uani 1 1 d U . .
H9A H 0.3959 0.1908 0.4865 0.037 Uiso 1 1 calc R . .
C8 C -0.2609(2) 0.23417(11) 0.63575(16) 0.0315(4) Uani 1 1 d U . .
H8A H -0.3310 0.2572 0.6764 0.038 Uiso 1 1 calc R . .
H8B H -0.3058 0.2296 0.5604 0.038 Uiso 1 1 calc R . .
C7 C 0.3003(2) 0.36004(10) 0.83573(16) 0.0307(4) Uani 1 1 d U . .
H7A H 0.3504 0.4016 0.8458 0.037 Uiso 1 1 calc R . .
C6 C 0.4517(2) 0.05154(10) 0.62860(18) 0.0312(4) Uani 1 1 d U . .
H6A H 0.5160 0.0145 0.6400 0.037 Uiso 1 1 calc R . .
C5 C -0.0093(2) 0.01039(9) 0.81744(16) 0.0282(4) Uani 1 1 d U . .
H5A H 0.0379 0.0220 0.8864 0.034 Uiso 1 1 calc R . .
C4 C 0.4774(2) 0.10232(10) 0.55493(17) 0.0308(4) Uani 1 1 d U . .
H4A H 0.5591 0.0997 0.5171 0.037 Uiso 1 1 calc R . .
C3 C -0.1739(2) -0.06499(10) 0.7037(2) 0.0337(5) Uani 1 1 d U . .
H3A H -0.2361 -0.1030 0.6965 0.040 Uiso 1 1 calc R . .
C2 C -0.1024(2) -0.04711(10) 0.80451(18) 0.0342(5) Uani 1 1 d U . .
H2A H -0.1160 -0.0736 0.8653 0.041 Uiso 1 1 calc R . .
C1 C -0.1224(2) 0.27729(10) 0.63956(16) 0.0306(4) Uani 1 1 d U . .
H1A H -0.0449 0.2506 0.6126 0.037 Uiso 1 1 calc R . .
H1B H -0.1418 0.3171 0.5926 0.037 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C18 1.380(2) . ?
O2 C8 1.432(2) . ?
O1 C23 1.391(2) . ?
O1 C1 1.426(2) . ?
C28 C23 1.396(2) . ?
C28 C14 1.393(2) . ?
C28 C27 1.487(2) . ?
C27 C20 1.350(2) . ?
C27 C16 1.496(2) . ?
C26 C10 1.387(3) . ?
C26 C16 1.399(3) . ?
C25 C9 1.397(2) . ?
C25 C17 1.404(2) . ?
C24 C6 1.396(2) . ?
C24 C17 1.394(2) . ?
C23 C22 1.383(2) . ?
C22 C7 1.391(3) . ?
C21 C18 1.380(3) . ?
C21 C11 1.378(3) . ?
C20 C13 1.487(2) . ?
C20 C17 1.493(2) . ?
C19 C15 1.387(3) . ?
C19 C3 1.387(3) . ?
C18 C16 1.395(2) . ?
C15 C13 1.390(3) . ?
C14 C12 1.395(3) . ?
C13 C5 1.397(3) . ?
C12 C7 1.394(3) . ?
C11 C10 1.403(3) . ?
C9 C4 1.387(3) . ?
C8 C1 1.513(3) . ?
C6 C4 1.381(3) . ?
C5 C2 1.402(3) . ?
C3 C2 1.372(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
C18 O2 C8 114.63(14) . . ?
C23 O1 C1 116.23(13) . . ?
C23 C28 C14 117.94(15) . . ?
C23 C28 C27 120.64(15) . . ?
C14 C28 C27 121.39(15) . . ?
C20 C27 C16 119.94(14) . . ?
C20 C27 C28 125.08(15) . . ?
C16 C27 C28 114.98(14) . . ?
C10 C26 C16 121.29(17) . . ?
C9 C25 C17 120.32(17) . . ?
C6 C24 C17 120.88(17) . . ?
C22 C23 C28 121.43(16) . . ?
C22 C23 O1 117.69(15) . . ?
C28 C23 O1 120.76(15) . . ?
C23 C22 C7 120.38(17) . . ?
C18 C21 C11 120.33(18) . . ?
C27 C20 C13 120.87(14) . . ?
C27 C20 C17 124.57(15) . . ?
C13 C20 C17 114.52(13) . . ?
C15 C19 C3 119.72(18) . . ?
C21 C18 C16 121.16(18) . . ?
C21 C18 O2 119.53(17) . . ?
C16 C18 O2 119.28(15) . . ?
C24 C17 C25 118.36(15) . . ?
C24 C17 C20 119.23(15) . . ?
C25 C17 C20 122.38(15) . . ?
C18 C16 C26 118.04(16) . . ?
C18 C16 C27 121.80(16) . . ?
C26 C16 C27 120.16(15) . . ?
C19 C15 C13 121.64(17) . . ?
C28 C14 C12 121.02(17) . . ?
C15 C13 C5 118.29(16) . . ?
C15 C13 C20 119.05(15) . . ?
C5 C13 C20 122.62(16) . . ?
C7 C12 C14 120.19(17) . . ?
C21 C11 C10 119.99(18) . . ?
C26 C10 C11 119.17(19) . . ?
C25 C9 C4 120.45(18) . . ?
O2 C8 C1 111.44(15) . . ?
C22 C7 C12 119.01(16) . . ?
C4 C6 C24 120.32(17) . . ?
C13 C5 C2 119.68(18) . . ?
C6 C4 C9 119.63(16) . . ?
C2 C3 C19 119.50(17) . . ?
C3 C2 C5 121.16(18) . . ?
O1 C1 C8 110.29(16) . . ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.500 0.500 108 43 ' '
2 0.500 1.000 0.000 108 43 ' '
_platon_squeeze_details          
;
;


_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        70.71
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.055

# 
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag 
# 
#data_1
_shelx_title                     ' 1 in P2(1)/n'
_shelx_refln_list_code           4
_shelx_F_calc_maximum            187.11
#_exptl_crystal_F_000       824.00 
_reflns_d_resolution_high        0.8167

#loop_ 
# _symmetry_equiv_pos_as_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     9.1319 
#_cell_length_b    19.4605 
#_cell_length_c    12.3122 
#_cell_angle_alpha  90.000 
#_cell_angle_beta   97.242 
#_cell_angle_gamma  90.000 

_shelx_F_squared_multiplier      1.000
####################################################################### 
# 
# 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_qq
_database_code_depnum_ccdc_archive 'CCDC 1820144'
_audit_update_record             
;
2018-01-26 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H26 O2'
_chemical_formula_weight         418.51

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   9.3824(12)
_cell_length_b                   9.3181(12)
_cell_length_c                   25.644(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.845(4)
_cell_angle_gamma                90
_cell_volume                     2221.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5553
_cell_measurement_theta_min      2.186
_cell_measurement_theta_max      23.527

_exptl_crystal_description       bloc
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26910
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.191
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3907
_reflns_number_gt                2564
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0795P)²+1.5356P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3907
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0731
_refine_ls_wR_factor_ref         0.1808
_refine_ls_wR_factor_gt          0.1640
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6085(2) 0.79933(19) 0.37335(8) 0.0475(8) Uani 1 1 d G . . . .
H1 H 0.609504 0.880789 0.352452 0.057 Uiso 1 1 calc R U . . .
C2 C 0.73551(16) 0.7499(2) 0.40201(9) 0.0538(9) Uani 1 1 d G . . . .
H2 H 0.821423 0.798307 0.400274 0.065 Uiso 1 1 calc R U . . .
C3 C 0.73407(17) 0.6282(2) 0.43325(8) 0.0552(9) Uani 1 1 d G . . . .
H3 H 0.819019 0.595090 0.452416 0.066 Uiso 1 1 calc R U . . .
C4 C 0.6057(2) 0.5558(2) 0.43583(8) 0.0554(9) Uani 1 1 d G . . . .
H4 H 0.604696 0.474354 0.456737 0.066 Uiso 1 1 calc R U . . .
C5 C 0.47869(17) 0.6052(2) 0.40718(8) 0.0465(8) Uani 1 1 d G . . . .
H5 H 0.392775 0.556833 0.408915 0.056 Uiso 1 1 calc R U . . .
C6 C 0.48013(16) 0.7270(2) 0.37594(7) 0.0360(7) Uani 1 1 d G . . . .
C7 C 0.3458(3) 0.7726(3) 0.34146(11) 0.0344(7) Uani 1 1 d . . . . .
C8 C 0.3579(2) 0.7761(2) 0.28364(5) 0.0337(7) Uani 1 1 d G . . . .
C9 C 0.44292(19) 0.67550(18) 0.26236(7) 0.0415(8) Uani 1 1 d G . . . .
H9 H 0.490277 0.604815 0.283727 0.050 Uiso 1 1 calc R U . . .
C10 C 0.4572(2) 0.6806(2) 0.20915(8) 0.0505(9) Uani 1 1 d G . . . .
H10 H 0.514139 0.613271 0.194916 0.061 Uiso 1 1 calc R U . . .
C11 C 0.3864(2) 0.7862(2) 0.17722(5) 0.0534(9) Uani 1 1 d G . . . .
H11 H 0.396011 0.789598 0.141621 0.064 Uiso 1 1 calc R U . . .
C12 C 0.3014(2) 0.8868(2) 0.19850(7) 0.0507(9) Uani 1 1 d G . . . .
H12 H 0.254020 0.957471 0.177135 0.061 Uiso 1 1 calc R U . . .
C13 C 0.28708(19) 0.88172(18) 0.25171(7) 0.0412(8) Uani 1 1 d G . . . .
H13 H 0.230157 0.949018 0.265946 0.049 Uiso 1 1 calc R U . . .
C14 C 0.2268(3) 0.8091(3) 0.36188(11) 0.0364(7) Uani 1 1 d . . . . .
C15 C 0.08282(15) 0.83417(19) 0.33010(7) 0.0343(7) Uani 1 1 d G . . . .
C16 C 0.0078(2) 0.72195(15) 0.30318(8) 0.0422(8) Uani 1 1 d G . . . .
H16 H 0.048203 0.630687 0.303979 0.051 Uiso 1 1 calc R U . . .
C17 C -0.12746(19) 0.74614(18) 0.27507(8) 0.0496(9) Uani 1 1 d G . . . .
H17 H -0.177620 0.671064 0.257062 0.060 Uiso 1 1 calc R U . . .
C18 C -0.18778(16) 0.8825(2) 0.27388(8) 0.0466(8) Uani 1 1 d G . . . .
H18 H -0.278303 0.898733 0.255071 0.056 Uiso 1 1 calc R U . . .
C19 C -0.11280(19) 0.99476(16) 0.30080(8) 0.0422(8) Uani 1 1 d G . . . .
H19 H -0.153165 1.086028 0.299997 0.051 Uiso 1 1 calc R U . . .
C20 C 0.02249(18) 0.97057(16) 0.32891(7) 0.0360(7) Uani 1 1 d G . . . .
C21 C 0.0560(4) 1.2149(3) 0.35556(14) 0.0539(9) Uani 1 1 d . . . . .
H21A H -0.020508 1.218938 0.377432 0.065 Uiso 1 1 calc R U . . .
H21B H 0.018722 1.249381 0.320667 0.065 Uiso 1 1 calc R U . . .
C22 C 0.1811(4) 1.3048(4) 0.37894(14) 0.0630(10) Uani 1 1 d . . . . .
H22A H 0.150259 1.404133 0.378773 0.076 Uiso 1 1 calc R U . . .
H22B H 0.255806 1.297907 0.356378 0.076 Uiso 1 1 calc R U . . .
C23 C 0.2457(4) 1.2659(4) 0.43423(14) 0.0618(10) Uani 1 1 d . . . . .
H23A H 0.174346 1.212420 0.450304 0.074 Uiso 1 1 calc R U . . .
H23B H 0.264363 1.354038 0.454101 0.074 Uiso 1 1 calc R U . . .
C24 C 0.3831(4) 1.1789(4) 0.44006(15) 0.0642(11) Uani 1 1 d . . . . .
H24A H 0.451754 1.227072 0.421002 0.077 Uiso 1 1 calc R U . . .
H24B H 0.423417 1.177321 0.476956 0.077 Uiso 1 1 calc R U . . .
C25 C 0.2240(2) 0.8250(2) 0.42015(6) 0.0399(7) Uani 1 1 d G . . . .
C26 C 0.2912(2) 0.9399(2) 0.44807(8) 0.0461(8) Uani 1 1 d G . . . .
C27 C 0.2804(3) 0.9560(2) 0.50127(8) 0.0664(11) Uani 1 1 d G . . . .
H27 H 0.325330 1.032848 0.519954 0.080 Uiso 1 1 calc R U . . .
C28 C 0.2023(3) 0.8573(3) 0.52655(6) 0.0745(12) Uani 1 1 d G . . . .
H28 H 0.195039 0.868114 0.562146 0.089 Uiso 1 1 calc R U . . .
C29 C 0.1351(3) 0.7425(3) 0.49863(9) 0.0702(12) Uani 1 1 d G . . . .
H29 H 0.082872 0.676435 0.515546 0.084 Uiso 1 1 calc R U . . .
C30 C 0.1460(2) 0.7263(2) 0.44543(8) 0.0528(9) Uani 1 1 d G . . . .
H30 H 0.100994 0.649489 0.426754 0.063 Uiso 1 1 calc R U . . .
O1 O 0.3667(2) 1.0331(3) 0.42149(8) 0.0543(6) Uani 1 1 d . . . . .
O2 O 0.1070(2) 1.0729(2) 0.35287(10) 0.0577(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C6 C7 1.499(3) . ?
C7 C14 1.340(4) . ?
C7 C8 1.502(3) . ?
C8 C9 1.3900 . ?
C8 C13 1.3900 . ?
C9 C10 1.3900 . ?
C10 C11 1.3900 . ?
C11 C12 1.3900 . ?
C12 C13 1.3900 . ?
C14 C15 1.498(3) . ?
C14 C25 1.506(3) . ?
C15 C16 1.3900 . ?
C15 C20 1.3900 . ?
C16 C17 1.3900 . ?
C17 C18 1.3900 . ?
C18 C19 1.3900 . ?
C19 C20 1.3900 . ?
C20 O2 1.335(2) . ?
C21 O2 1.412(4) . ?
C21 C22 1.499(5) . ?
C22 C23 1.508(5) . ?
C23 C24 1.513(5) . ?
C24 O1 1.440(4) . ?
C25 C26 1.3900 . ?
C25 C30 1.3900 . ?
C26 O1 1.362(3) . ?
C26 C27 1.3900 . ?
C27 C28 1.3900 . ?
C28 C29 1.3900 . ?
C29 C30 1.3900 . ?

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 C1 C6 120.0 . . ?
C3 C2 C1 120.0 . . ?
C2 C3 C4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 C7 119.88(16) . . ?
C1 C6 C7 119.90(16) . . ?
C14 C7 C6 121.3(3) . . ?
C14 C7 C8 124.0(2) . . ?
C6 C7 C8 114.7(2) . . ?
C9 C8 C13 120.0 . . ?
C9 C8 C7 119.83(15) . . ?
C13 C8 C7 120.15(15) . . ?
C10 C9 C8 120.0 . . ?
C9 C10 C11 120.0 . . ?
C12 C11 C10 120.0 . . ?
C13 C12 C11 120.0 . . ?
C12 C13 C8 120.0 . . ?
C7 C14 C15 124.4(3) . . ?
C7 C14 C25 122.8(3) . . ?
C15 C14 C25 112.8(2) . . ?
C16 C15 C20 120.0 . . ?
C16 C15 C14 120.73(16) . . ?
C20 C15 C14 119.25(16) . . ?
C15 C16 C17 120.0 . . ?
C18 C17 C16 120.0 . . ?
C17 C18 C19 120.0 . . ?
C20 C19 C18 120.0 . . ?
O2 C20 C19 124.45(15) . . ?
O2 C20 C15 115.38(15) . . ?
C19 C20 C15 120.0 . . ?
O2 C21 C22 106.9(3) . . ?
C21 C22 C23 115.7(3) . . ?
C22 C23 C24 116.7(3) . . ?
O1 C24 C23 114.9(3) . . ?
C26 C25 C30 120.0 . . ?
C26 C25 C14 121.25(17) . . ?
C30 C25 C14 118.66(17) . . ?
O1 C26 C27 122.36(17) . . ?
O1 C26 C25 117.64(17) . . ?
C27 C26 C25 120.0 . . ?
C26 C27 C28 120.0 . . ?
C29 C28 C27 120.0 . . ?
C30 C29 C28 120.0 . . ?
C29 C30 C25 120.0 . . ?
C26 O1 C24 118.4(2) . . ?
C20 O2 C21 120.5(2) . . ?

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.047

