# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_140528a
_database_code_depnum_ccdc_archive 'CCDC 1543218'
_audit_update_record             
;
2017-04-10 deposited with the CCDC.
2018-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 O'
_chemical_formula_weight         282.32

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'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   P21/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                   9.533(6)
_cell_length_b                   17.215(10)
_cell_length_c                   11.031(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 122.95(4)
_cell_angle_gamma                90.00
_cell_volume                     1519.1(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2616
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       PLATELET
_exptl_crystal_colour            RED
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9795
_exptl_absorpt_correction_T_max  0.9970
_exptl_absorpt_process_details   REQAB

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury375R'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 13.6612
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15840
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3492
_reflns_number_gt                2397
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CRYSTALCLEAR
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_reduction        CRYSTALCLEAR
_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)+(0.0503P)²+0.1628P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3492
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1281
_refine_ls_wR_factor_gt          0.1141
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.38602(15) 0.91905(8) -0.07603(12) 0.0764(4) Uani 1 1 d . . .
C1 C -0.1236(2) 0.90488(9) -0.05923(16) 0.0574(4) Uani 1 1 d . . .
C2 C -0.1516(3) 0.92509(11) -0.19109(18) 0.0708(5) Uani 1 1 d . . .
H2 H -0.2572 0.9403 -0.2668 0.085 Uiso 1 1 calc R . .
C3 C -0.0176(3) 0.92211(11) -0.2082(2) 0.0785(6) Uani 1 1 d . . .
H3 H -0.0338 0.9355 -0.2967 0.094 Uiso 1 1 calc R . .
C4 C 0.1378(3) 0.89981(11) -0.0968(2) 0.0756(5) Uani 1 1 d . . .
H4 H 0.2257 0.8985 -0.1106 0.091 Uiso 1 1 calc R . .
C5 C 0.1668(2) 0.87884(10) 0.0378(2) 0.0661(5) Uani 1 1 d . . .
H5 H 0.2725 0.8636 0.1134 0.079 Uiso 1 1 calc R . .
C6 C 0.0343(2) 0.88141(8) 0.05484(17) 0.0541(4) Uani 1 1 d . . .
C7 C 0.02469(19) 0.86675(8) 0.18342(16) 0.0511(4) Uani 1 1 d . . .
C8 C -0.13259(19) 0.88125(8) 0.15018(16) 0.0518(4) Uani 1 1 d . . .
C9 C -0.2373(2) 0.90487(9) -0.00639(17) 0.0572(4) Uani 1 1 d . . .
C10 C -0.20158(19) 0.87597(9) 0.24104(16) 0.0521(4) Uani 1 1 d . . .
C11 C -0.1542(2) 0.81686(10) 0.34326(17) 0.0620(4) Uani 1 1 d . . .
H11 H -0.0800 0.7786 0.3527 0.074 Uiso 1 1 calc R . .
C12 C -0.2167(2) 0.81513(12) 0.4298(2) 0.0735(5) Uani 1 1 d . . .
H12 H -0.1828 0.7761 0.4987 0.088 Uiso 1 1 calc R . .
C13 C -0.3292(3) 0.87052(13) 0.4158(2) 0.0763(6) Uani 1 1 d . . .
H13 H -0.3704 0.8691 0.4753 0.092 Uiso 1 1 calc R . .
C14 C -0.3801(2) 0.92782(12) 0.3132(2) 0.0739(5) Uani 1 1 d . . .
H14 H -0.4571 0.9648 0.3024 0.089 Uiso 1 1 calc R . .
C15 C -0.3176(2) 0.93067(10) 0.22642(18) 0.0630(4) Uani 1 1 d . . .
H15 H -0.3532 0.9696 0.1572 0.076 Uiso 1 1 calc R . .
C16 C 0.17154(18) 0.84251(9) 0.32411(16) 0.0547(4) Uani 1 1 d . . .
C17 C 0.2163(2) 0.88195(11) 0.44998(17) 0.0673(5) Uani 1 1 d . . .
H17 H 0.1548 0.9250 0.4458 0.081 Uiso 1 1 calc R . .
C18 C 0.3518(2) 0.85751(14) 0.5815(2) 0.0842(6) Uani 1 1 d . . .
H18 H 0.3811 0.8842 0.6654 0.101 Uiso 1 1 calc R . .
C19 C 0.4429(2) 0.79410(16) 0.5888(3) 0.0925(8) Uani 1 1 d . . .
H19 H 0.5330 0.7775 0.6777 0.111 Uiso 1 1 calc R . .
C20 C 0.4017(2) 0.75520(13) 0.4655(3) 0.0849(6) Uani 1 1 d . . .
H20 H 0.4642 0.7123 0.4709 0.102 Uiso 1 1 calc R . .
C21 C 0.2676(2) 0.77937(11) 0.3330(2) 0.0672(5) Uani 1 1 d . . .
H21 H 0.2415 0.7532 0.2495 0.081 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 C9 1.215(2) . ?
C1 C2 1.373(2) . ?
C1 C6 1.397(2) . ?
C1 C9 1.483(3) . ?
C2 C3 1.390(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.402(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.492(2) . ?
C7 C8 1.359(2) . ?
C7 C16 1.476(2) . ?
C8 C10 1.471(2) . ?
C8 C9 1.506(2) . ?
C10 C15 1.393(2) . ?
C10 C11 1.399(2) . ?
C11 C12 1.373(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.388(2) . ?
C16 C21 1.390(2) . ?
C17 C18 1.383(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.370(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.383(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.39(18) . . ?
C2 C1 C9 130.81(17) . . ?
C6 C1 C9 107.77(14) . . ?
C1 C2 C3 118.11(19) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C4 C3 C2 120.94(18) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 121.1(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 118.02(19) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C1 120.39(16) . . ?
C5 C6 C7 131.32(16) . . ?
C1 C6 C7 108.20(15) . . ?
C8 C7 C16 127.72(15) . . ?
C8 C7 C6 109.97(14) . . ?
C16 C7 C6 122.28(15) . . ?
C7 C8 C10 129.91(14) . . ?
C7 C8 C9 107.73(15) . . ?
C10 C8 C9 122.36(14) . . ?
O1 C9 C1 127.04(16) . . ?
O1 C9 C8 126.64(17) . . ?
C1 C9 C8 106.30(14) . . ?
C15 C10 C11 118.22(16) . . ?
C15 C10 C8 120.02(14) . . ?
C11 C10 C8 121.75(15) . . ?
C12 C11 C10 120.26(17) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.80(18) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 119.51(18) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 120.37(19) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 120.79(17) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C17 C16 C21 118.66(16) . . ?
C17 C16 C7 120.87(15) . . ?
C21 C16 C7 120.47(16) . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 120.3(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 120.12(19) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.3(2) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 120.3(2) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?

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
C6 C1 C2 C3 -0.4(3) . . . . ?
C9 C1 C2 C3 177.49(17) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
C4 C5 C6 C7 -176.71(16) . . . . ?
C2 C1 C6 C5 0.7(2) . . . . ?
C9 C1 C6 C5 -177.62(14) . . . . ?
C2 C1 C6 C7 177.75(15) . . . . ?
C9 C1 C6 C7 -0.58(17) . . . . ?
C5 C6 C7 C8 176.10(16) . . . . ?
C1 C6 C7 C8 -0.50(17) . . . . ?
C5 C6 C7 C16 -2.1(2) . . . . ?
C1 C6 C7 C16 -178.72(14) . . . . ?
C16 C7 C8 C10 -1.2(3) . . . . ?
C6 C7 C8 C10 -179.25(14) . . . . ?
C16 C7 C8 C9 179.43(14) . . . . ?
C6 C7 C8 C9 1.34(17) . . . . ?
C2 C1 C9 O1 5.0(3) . . . . ?
C6 C1 C9 O1 -176.91(17) . . . . ?
C2 C1 C9 C8 -176.77(17) . . . . ?
C6 C1 C9 C8 1.35(17) . . . . ?
C7 C8 C9 O1 176.60(16) . . . . ?
C10 C8 C9 O1 -2.9(3) . . . . ?
C7 C8 C9 C1 -1.66(17) . . . . ?
C10 C8 C9 C1 178.87(13) . . . . ?
C7 C8 C10 C15 142.10(17) . . . . ?
C9 C8 C10 C15 -38.6(2) . . . . ?
C7 C8 C10 C11 -38.0(2) . . . . ?
C9 C8 C10 C11 141.36(15) . . . . ?
C15 C10 C11 C12 -2.3(2) . . . . ?
C8 C10 C11 C12 177.78(15) . . . . ?
C10 C11 C12 C13 1.2(3) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C13 C14 C15 C10 -0.2(3) . . . . ?
C11 C10 C15 C14 1.8(2) . . . . ?
C8 C10 C15 C14 -178.25(15) . . . . ?
C8 C7 C16 C17 -49.6(2) . . . . ?
C6 C7 C16 C17 128.33(17) . . . . ?
C8 C7 C16 C21 130.22(18) . . . . ?
C6 C7 C16 C21 -51.9(2) . . . . ?
C21 C16 C17 C18 -1.3(3) . . . . ?
C7 C16 C17 C18 178.45(16) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C17 C18 C19 C20 0.9(3) . . . . ?
C18 C19 C20 C21 -0.3(3) . . . . ?
C19 C20 C21 C16 -1.2(3) . . . . ?
C17 C16 C21 C20 1.9(3) . . . . ?
C7 C16 C21 C20 -177.84(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.029

####################################################################### 
# 
# 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_150518a
_database_code_depnum_ccdc_archive 'CCDC 1543219'
_audit_update_record             
;
2017-04-10 deposited with the CCDC.
2018-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 O'
_chemical_formula_weight         234.28

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'

_symmetry_cell_setting           TRICLINIC
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.166(4)
_cell_length_b                   9.066(5)
_cell_length_c                   9.404(6)
_cell_angle_alpha                85.402(19)
_cell_angle_beta                 75.824(17)
_cell_angle_gamma                71.601(17)
_cell_volume                     640.5(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    1594
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             248
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9854
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury375R'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 13.6612
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6732
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         27.47
_reflns_number_total             2917
_reflns_number_gt                2208
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CRYSTALCLEAR
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_reduction        CRYSTALCLEAR
_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)+(0.0669P)²+0.0413P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2917
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1288
_refine_ls_wR_factor_gt          0.1187
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.19601(16) 0.79561(15) 0.42309(16) 0.0488(3) Uani 1 1 d . . .
C2 C 1.05494(16) 0.81136(14) 0.34225(15) 0.0464(3) Uani 1 1 d . . .
C3 C 1.05419(19) 0.83739(16) 0.19656(15) 0.0559(4) Uani 1 1 d . . .
H3 H 1.1527 0.8514 0.1293 0.067 Uiso 1 1 calc R . .
C4 C 0.9011(2) 0.84232(17) 0.15213(16) 0.0591(4) Uani 1 1 d . . .
H4 H 0.8973 0.8595 0.0540 0.071 Uiso 1 1 calc R . .
C5 C 0.75629(19) 0.82180(17) 0.25290(16) 0.0551(4) Uani 1 1 d . . .
H5 H 0.6556 0.8252 0.2215 0.066 Uiso 1 1 calc R . .
C6 C 0.75685(17) 0.79595(15) 0.40135(15) 0.0498(3) Uani 1 1 d . . .
H6 H 0.6580 0.7828 0.4686 0.060 Uiso 1 1 calc R . .
C7 C 0.90764(16) 0.79051(14) 0.44541(13) 0.0434(3) Uani 1 1 d . . .
C8 C 0.95279(16) 0.76085(14) 0.59192(14) 0.0440(3) Uani 1 1 d . . .
C9 C 1.12037(17) 0.76445(15) 0.57995(15) 0.0477(3) Uani 1 1 d . . .
C10 C 0.82812(16) 0.73224(15) 0.72643(13) 0.0439(3) Uani 1 1 d . . .
C11 C 0.87412(19) 0.59707(16) 0.80773(16) 0.0562(4) Uani 1 1 d . . .
H11 H 0.9841 0.5231 0.7768 0.067 Uiso 1 1 calc R . .
C12 C 0.7580(2) 0.57140(18) 0.93423(16) 0.0629(4) Uani 1 1 d . . .
H12 H 0.7904 0.4802 0.9875 0.076 Uiso 1 1 calc R . .
C13 C 0.59459(19) 0.68004(18) 0.98211(15) 0.0554(4) Uani 1 1 d . . .
H13 H 0.5171 0.6628 1.0676 0.067 Uiso 1 1 calc R . .
C14 C 0.54734(19) 0.81408(17) 0.90222(16) 0.0576(4) Uani 1 1 d . . .
H14 H 0.4376 0.8881 0.9343 0.069 Uiso 1 1 calc R . .
C15 C 0.66206(18) 0.83976(16) 0.77436(16) 0.0547(4) Uani 1 1 d . . .
H15 H 0.6276 0.9298 0.7201 0.066 Uiso 1 1 calc R . .
C16 C 1.22229(19) 0.74766(18) 0.69548(17) 0.0573(4) Uani 1 1 d . . .
H16A H 1.1416 0.7538 0.7911 0.069 Uiso 1 1 calc R . .
H16B H 1.2704 0.8339 0.6872 0.069 Uiso 1 1 calc R . .
C17 C 1.3736(2) 0.59615(19) 0.68592(19) 0.0661(4) Uani 1 1 d . . .
H17A H 1.3271 0.5100 0.6954 0.099 Uiso 1 1 calc R . .
H17B H 1.4326 0.5921 0.7634 0.099 Uiso 1 1 calc R . .
H17C H 1.4565 0.5907 0.5929 0.099 Uiso 1 1 calc R . .
O1 O 1.34407(12) 0.80611(13) 0.37171(13) 0.0680(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.2180(16) . ?
C1 C2 1.494(2) . ?
C1 C9 1.495(2) . ?
C2 C3 1.373(2) . ?
C2 C7 1.4023(18) . ?
C3 C4 1.399(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.3780(19) . ?
C6 H6 0.9300 . ?
C7 C8 1.494(2) . ?
C8 C9 1.3560(19) . ?
C8 C10 1.4789(18) . ?
C9 C16 1.494(2) . ?
C10 C11 1.388(2) . ?
C10 C15 1.3889(19) . ?
C11 C12 1.382(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.522(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
O1 C1 C2 126.88(14) . . ?
O1 C1 C9 126.41(13) . . ?
C2 C1 C9 106.71(11) . . ?
C3 C2 C7 121.80(13) . . ?
C3 C2 C1 131.30(12) . . ?
C7 C2 C1 106.88(12) . . ?
C2 C3 C4 118.11(13) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 120.32(14) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 121.55(14) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 118.28(13) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C6 C7 C2 119.94(13) . . ?
C6 C7 C8 131.57(12) . . ?
C2 C7 C8 108.48(12) . . ?
C9 C8 C10 127.08(12) . . ?
C9 C8 C7 109.78(11) . . ?
C10 C8 C7 123.14(12) . . ?
C8 C9 C16 129.91(13) . . ?
C8 C9 C1 108.15(12) . . ?
C16 C9 C1 121.91(12) . . ?
C11 C10 C15 118.38(12) . . ?
C11 C10 C8 120.79(12) . . ?
C15 C10 C8 120.83(12) . . ?
C12 C11 C10 120.66(13) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 120.50(14) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 119.36(13) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 120.48(13) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 120.61(13) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C9 C16 C17 113.63(12) . . ?
C9 C16 H16A 108.8 . . ?
C17 C16 H16A 108.8 . . ?
C9 C16 H16B 108.8 . . ?
C17 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 1.3(2) . . . . ?
C9 C1 C2 C3 -178.69(13) . . . . ?
O1 C1 C2 C7 179.97(13) . . . . ?
C9 C1 C2 C7 -0.07(14) . . . . ?
C7 C2 C3 C4 -0.2(2) . . . . ?
C1 C2 C3 C4 178.25(13) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C4 C5 C6 C7 -0.3(2) . . . . ?
C5 C6 C7 C2 0.27(19) . . . . ?
C5 C6 C7 C8 -177.92(12) . . . . ?
C3 C2 C7 C6 -0.01(19) . . . . ?
C1 C2 C7 C6 -178.79(11) . . . . ?
C3 C2 C7 C8 178.56(12) . . . . ?
C1 C2 C7 C8 -0.22(14) . . . . ?
C6 C7 C8 C9 178.81(13) . . . . ?
C2 C7 C8 C9 0.46(15) . . . . ?
C6 C7 C8 C10 -1.1(2) . . . . ?
C2 C7 C8 C10 -179.45(11) . . . . ?
C10 C8 C9 C16 -2.7(2) . . . . ?
C7 C8 C9 C16 177.41(13) . . . . ?
C10 C8 C9 C1 179.41(12) . . . . ?
C7 C8 C9 C1 -0.50(14) . . . . ?
O1 C1 C9 C8 -179.68(13) . . . . ?
C2 C1 C9 C8 0.36(14) . . . . ?
O1 C1 C9 C16 2.2(2) . . . . ?
C2 C1 C9 C16 -177.75(11) . . . . ?
C9 C8 C10 C11 -57.01(19) . . . . ?
C7 C8 C10 C11 122.89(14) . . . . ?
C9 C8 C10 C15 123.12(16) . . . . ?
C7 C8 C10 C15 -56.98(18) . . . . ?
C15 C10 C11 C12 -0.8(2) . . . . ?
C8 C10 C11 C12 179.33(13) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
C11 C12 C13 C14 0.4(2) . . . . ?
C12 C13 C14 C15 0.4(2) . . . . ?
C13 C14 C15 C10 -1.4(2) . . . . ?
C11 C10 C15 C14 1.6(2) . . . . ?
C8 C10 C15 C14 -178.52(13) . . . . ?
C8 C9 C16 C17 109.87(17) . . . . ?
C1 C9 C16 C17 -72.48(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.030

####################################################################### 
# 
# 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_m20170418c1
_database_code_depnum_ccdc_archive 'CCDC 1545304'
_audit_update_record             
;
2017-04-21 deposited with the CCDC.
2018-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H18 O'
_chemical_formula_weight         358.41

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.603(3)
_cell_length_b                   10.694(4)
_cell_length_c                   10.7294(16)
_cell_angle_alpha                70.55(5)
_cell_angle_beta                 64.18(5)
_cell_angle_gamma                81.02(6)
_cell_volume                     935.1(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    128(2)
_cell_measurement_reflns_used    2128
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.4

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9850
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      128(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 5.814
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11911
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_sigmaI/netI    0.0529
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         27.52
_reflns_number_total             4193
_reflns_number_gt                2797
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'

_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)+(0.0832P)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    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4193
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.1523
_refine_ls_wR_factor_gt          0.1441
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.005
_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
O1 O 0.80423(16) 0.50209(13) 0.28061(13) 0.0515(4) Uani 1 1 d . . .
C1 C 0.7924(2) 0.51708(18) 0.39272(19) 0.0407(4) Uani 1 1 d . . .
C2 C 0.72321(19) 0.42209(17) 0.54308(18) 0.0379(4) Uani 1 1 d . . .
C3 C 0.73823(18) 0.47483(17) 0.63604(18) 0.0369(4) Uani 1 1 d . . .
C4 C 0.81185(18) 0.60775(17) 0.55432(17) 0.0372(4) Uani 1 1 d . . .
C5 C 0.84628(19) 0.63309(17) 0.40767(18) 0.0382(4) Uani 1 1 d . . .
C6 C 0.90756(19) 0.75099(18) 0.30589(19) 0.0399(4) Uani 1 1 d . . .
H6 H 0.9322 0.7644 0.2065 0.048 Uiso 1 1 calc R . .
C7 C 0.93347(18) 0.85173(17) 0.35028(18) 0.0385(4) Uani 1 1 d . . .
C8 C 0.89842(19) 0.82597(18) 0.49747(19) 0.0406(4) Uani 1 1 d . . .
H8 H 0.9160 0.8930 0.5288 0.049 Uiso 1 1 calc R . .
C9 C 0.83839(19) 0.70468(18) 0.59964(19) 0.0405(4) Uani 1 1 d . . .
H9 H 0.8162 0.6892 0.6989 0.049 Uiso 1 1 calc R . .
C10 C 0.99638(19) 0.98196(18) 0.24491(19) 0.0399(4) Uani 1 1 d . . .
C11 C 0.9391(2) 1.09989(18) 0.2802(2) 0.0428(4) Uani 1 1 d . . .
H11 H 0.8574 1.0968 0.3722 0.051 Uiso 1 1 calc R . .
C12 C 1.0003(2) 1.2210(2) 0.1826(2) 0.0492(5) Uani 1 1 d . . .
H12 H 0.9601 1.3004 0.2079 0.059 Uiso 1 1 calc R . .
C13 C 1.1200(2) 1.2269(2) 0.0480(2) 0.0513(5) Uani 1 1 d . . .
H13 H 1.1624 1.3100 -0.0187 0.062 Uiso 1 1 calc R . .
C14 C 1.1768(2) 1.1114(2) 0.0117(2) 0.0500(5) Uani 1 1 d . . .
H14 H 1.2591 1.1151 -0.0801 0.060 Uiso 1 1 calc R . .
C15 C 1.1152(2) 0.99020(19) 0.10775(19) 0.0436(4) Uani 1 1 d . . .
H15 H 1.1540 0.9116 0.0803 0.052 Uiso 1 1 calc R . .
C16 C 0.65515(19) 0.29524(17) 0.57360(18) 0.0386(4) Uani 1 1 d . . .
C17 C 0.5597(2) 0.28847(18) 0.5077(2) 0.0433(4) Uani 1 1 d . . .
H17 H 0.5440 0.3651 0.4382 0.052 Uiso 1 1 calc R . .
C18 C 0.4886(2) 0.1722(2) 0.5426(2) 0.0485(5) Uani 1 1 d . . .
H18 H 0.4224 0.1696 0.4986 0.058 Uiso 1 1 calc R . .
C19 C 0.5125(2) 0.0589(2) 0.6410(2) 0.0518(5) Uani 1 1 d . . .
H19 H 0.4623 -0.0211 0.6655 0.062 Uiso 1 1 calc R . .
C20 C 0.6108(2) 0.06291(19) 0.7039(2) 0.0495(5) Uani 1 1 d . . .
H20 H 0.6293 -0.0151 0.7703 0.059 Uiso 1 1 calc R . .
C21 C 0.6812(2) 0.17947(18) 0.67043(19) 0.0423(4) Uani 1 1 d . . .
H21 H 0.7483 0.1812 0.7138 0.051 Uiso 1 1 calc R . .
C22 C 0.68591(19) 0.41924(17) 0.79543(18) 0.0380(4) Uani 1 1 d . . .
C23 C 0.5417(2) 0.35976(18) 0.88193(19) 0.0437(4) Uani 1 1 d . . .
H23 H 0.4763 0.3545 0.8382 0.052 Uiso 1 1 calc R . .
C24 C 0.4931(2) 0.3086(2) 1.0297(2) 0.0552(5) Uani 1 1 d . . .
H24 H 0.3947 0.2682 1.0871 0.066 Uiso 1 1 calc R . .
C25 C 0.5857(3) 0.3155(2) 1.0952(2) 0.0595(6) Uani 1 1 d . . .
H25 H 0.5515 0.2794 1.1974 0.071 Uiso 1 1 calc R . .
C26 C 0.7288(3) 0.3752(2) 1.0122(2) 0.0553(5) Uani 1 1 d . . .
H26 H 0.7926 0.3807 1.0574 0.066 Uiso 1 1 calc R . .
C27 C 0.7788(2) 0.42682(18) 0.8630(2) 0.0449(4) Uani 1 1 d . . .
H27 H 0.8770 0.4677 0.8062 0.054 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.220(2) . ?
C1 C5 1.496(3) . ?
C1 C2 1.504(3) . ?
C2 C3 1.363(2) . ?
C2 C16 1.473(3) . ?
C3 C22 1.483(2) . ?
C3 C4 1.494(3) . ?
C4 C9 1.379(2) . ?
C4 C5 1.396(2) . ?
C5 C6 1.372(3) . ?
C6 C7 1.406(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.400(2) . ?
C7 C10 1.484(3) . ?
C8 C9 1.397(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.399(3) . ?
C10 C15 1.399(3) . ?
C11 C12 1.385(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.395(3) . ?
C16 C17 1.402(2) . ?
C17 C18 1.373(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.391(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.376(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C27 1.397(2) . ?
C22 C23 1.395(3) . ?
C23 C24 1.374(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.374(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.387(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?

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
O1 C1 C5 126.76(17) . . ?
O1 C1 C2 127.06(17) . . ?
C5 C1 C2 106.17(15) . . ?
C3 C2 C16 129.35(16) . . ?
C3 C2 C1 108.11(16) . . ?
C16 C2 C1 122.54(16) . . ?
C2 C3 C22 128.32(16) . . ?
C2 C3 C4 109.58(15) . . ?
C22 C3 C4 122.03(15) . . ?
C9 C4 C5 119.21(16) . . ?
C9 C4 C3 131.97(15) . . ?
C5 C4 C3 108.65(15) . . ?
C6 C5 C4 122.33(16) . . ?
C6 C5 C1 130.03(16) . . ?
C4 C5 C1 107.45(16) . . ?
C5 C6 C7 119.30(16) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C8 C7 C6 118.14(17) . . ?
C8 C7 C10 120.50(16) . . ?
C6 C7 C10 121.36(15) . . ?
C9 C8 C7 121.97(17) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C4 C9 C8 119.04(16) . . ?
C4 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C11 C10 C15 118.14(18) . . ?
C11 C10 C7 120.92(16) . . ?
C15 C10 C7 120.94(17) . . ?
C12 C11 C10 120.72(18) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 119.5(2) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 120.63(19) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 120.72(19) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C21 C16 C17 118.22(17) . . ?
C21 C16 C2 121.21(16) . . ?
C17 C16 C2 120.55(16) . . ?
C18 C17 C16 120.65(18) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 120.61(18) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C20 119.45(18) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 120.20(18) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C16 120.81(17) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
C27 C22 C23 118.34(16) . . ?
C27 C22 C3 120.87(16) . . ?
C23 C22 C3 120.78(16) . . ?
C24 C23 C22 120.73(19) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 C23 120.6(2) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 119.97(19) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C27 119.8(2) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C26 C27 C22 120.56(18) . . ?
C26 C27 H27 119.7 . . ?
C22 C27 H27 119.7 . . ?

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 177.76(17) . . . . ?
C5 C1 C2 C3 -1.37(18) . . . . ?
O1 C1 C2 C16 -1.6(3) . . . . ?
C5 C1 C2 C16 179.28(14) . . . . ?
C16 C2 C3 C22 -1.6(3) . . . . ?
C1 C2 C3 C22 179.06(15) . . . . ?
C16 C2 C3 C4 -178.70(15) . . . . ?
C1 C2 C3 C4 2.01(18) . . . . ?
C2 C3 C4 C9 173.06(17) . . . . ?
C22 C3 C4 C9 -4.2(3) . . . . ?
C2 C3 C4 C5 -1.96(18) . . . . ?
C22 C3 C4 C5 -179.23(14) . . . . ?
C9 C4 C5 C6 0.8(2) . . . . ?
C3 C4 C5 C6 176.50(14) . . . . ?
C9 C4 C5 C1 -174.74(14) . . . . ?
C3 C4 C5 C1 1.01(17) . . . . ?
O1 C1 C5 C6 6.0(3) . . . . ?
C2 C1 C5 C6 -174.87(16) . . . . ?
O1 C1 C5 C4 -178.98(17) . . . . ?
C2 C1 C5 C4 0.16(17) . . . . ?
C4 C5 C6 C7 -1.6(2) . . . . ?
C1 C5 C6 C7 172.76(16) . . . . ?
C5 C6 C7 C8 1.4(2) . . . . ?
C5 C6 C7 C10 -178.69(15) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
C10 C7 C8 C9 179.70(15) . . . . ?
C5 C4 C9 C8 0.3(2) . . . . ?
C3 C4 C9 C8 -174.29(16) . . . . ?
C7 C8 C9 C4 -0.5(2) . . . . ?
C8 C7 C10 C11 -40.6(2) . . . . ?
C6 C7 C10 C11 139.50(17) . . . . ?
C8 C7 C10 C15 139.02(17) . . . . ?
C6 C7 C10 C15 -40.9(2) . . . . ?
C15 C10 C11 C12 -0.9(2) . . . . ?
C7 C10 C11 C12 178.73(15) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C10 -1.5(3) . . . . ?
C11 C10 C15 C14 1.7(2) . . . . ?
C7 C10 C15 C14 -177.92(15) . . . . ?
C3 C2 C16 C21 -40.9(3) . . . . ?
C1 C2 C16 C21 138.31(17) . . . . ?
C3 C2 C16 C17 137.88(19) . . . . ?
C1 C2 C16 C17 -42.9(2) . . . . ?
C21 C16 C17 C18 2.8(3) . . . . ?
C2 C16 C17 C18 -176.05(16) . . . . ?
C16 C17 C18 C19 -1.4(3) . . . . ?
C17 C18 C19 C20 -0.6(3) . . . . ?
C18 C19 C20 C21 1.2(3) . . . . ?
C19 C20 C21 C16 0.2(3) . . . . ?
C17 C16 C21 C20 -2.1(3) . . . . ?
C2 C16 C21 C20 176.65(16) . . . . ?
C2 C3 C22 C27 138.97(19) . . . . ?
C4 C3 C22 C27 -44.3(2) . . . . ?
C2 C3 C22 C23 -42.0(3) . . . . ?
C4 C3 C22 C23 134.75(17) . . . . ?
C27 C22 C23 C24 -0.7(3) . . . . ?
C3 C22 C23 C24 -179.80(16) . . . . ?
C22 C23 C24 C25 0.2(3) . . . . ?
C23 C24 C25 C26 0.4(3) . . . . ?
C24 C25 C26 C27 -0.5(3) . . . . ?
C25 C26 C27 C22 0.0(3) . . . . ?
C23 C22 C27 C26 0.6(3) . . . . ?
C3 C22 C27 C26 179.70(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_m20170419a1
_database_code_depnum_ccdc_archive 'CCDC 1545305'
_audit_update_record             
;
2017-04-21 deposited with the CCDC.
2018-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H20 O'
_chemical_formula_weight         408.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4085(15)
_cell_length_b                   9.3500(16)
_cell_length_c                   14.153(3)
_cell_angle_alpha                105.907(10)
_cell_angle_beta                 95.411(18)
_cell_angle_gamma                97.753(13)
_cell_volume                     1050.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    128(2)
_cell_measurement_reflns_used    2654
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9849
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      128(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 5.814
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13536
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         27.55
_reflns_number_total             4741
_reflns_number_gt                3582
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'

_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)+(0.0736P)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    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4741
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1221
_refine_ls_wR_factor_gt          0.1172
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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 1.08591(12) 0.09743(11) 0.34313(7) 0.0353(3) Uani 1 1 d . . .
C1 C 1.00558(16) 0.16894(14) 0.39978(10) 0.0267(3) Uani 1 1 d . . .
C2 C 1.04950(15) 0.23898(14) 0.50957(10) 0.0255(3) Uani 1 1 d . . .
C3 C 0.92235(15) 0.30308(14) 0.54487(10) 0.0242(3) Uani 1 1 d . . .
C4 C 0.79032(15) 0.28141(14) 0.46164(9) 0.0248(3) Uani 1 1 d . . .
C5 C 0.84110(16) 0.20372(15) 0.37357(10) 0.0264(3) Uani 1 1 d . . .
C6 C 0.74385(16) 0.16362(15) 0.28422(10) 0.0297(3) Uani 1 1 d . . .
H6 H 0.7821 0.1129 0.2251 0.036 Uiso 1 1 calc R . .
C7 C 0.58539(16) 0.19888(15) 0.28128(10) 0.0296(3) Uani 1 1 d . . .
C8 C 0.53441(16) 0.27252(15) 0.36940(10) 0.0300(3) Uani 1 1 d . . .
H8 H 0.4273 0.2946 0.3679 0.036 Uiso 1 1 calc R . .
C9 C 0.63482(16) 0.31527(15) 0.46015(10) 0.0271(3) Uani 1 1 d . . .
H9 H 0.5975 0.3664 0.5195 0.032 Uiso 1 1 calc R . .
C10 C 0.47176(17) 0.15182(16) 0.18658(10) 0.0316(3) Uani 1 1 d . . .
C11 C 0.33199(17) 0.05098(16) 0.17591(11) 0.0341(3) Uani 1 1 d . . .
H11 H 0.3097 0.0121 0.2295 0.041 Uiso 1 1 calc R . .
C12 C 0.22102(18) 0.00332(18) 0.08863(12) 0.0413(4) Uani 1 1 d . . .
H12 H 0.1263 -0.0681 0.0831 0.050 Uiso 1 1 calc R . .
C13 C 0.25014(19) 0.06083(18) 0.01090(12) 0.0421(4) Uani 1 1 d . . .
H13 H 0.1747 0.0295 -0.0481 0.051 Uiso 1 1 calc R . .
C14 C 0.39171(17) 0.16614(16) 0.01849(10) 0.0332(3) Uani 1 1 d . . .
C15 C 0.4246(2) 0.22913(19) -0.05933(11) 0.0428(4) Uani 1 1 d . . .
H15 H 0.3500 0.1990 -0.1187 0.051 Uiso 1 1 calc R . .
C16 C 0.5591(2) 0.33091(19) -0.05153(12) 0.0446(4) Uani 1 1 d . . .
H16 H 0.5780 0.3719 -0.1047 0.054 Uiso 1 1 calc R . .
C17 C 0.6701(2) 0.37546(18) 0.03501(11) 0.0389(4) Uani 1 1 d . . .
H17 H 0.7643 0.4472 0.0400 0.047 Uiso 1 1 calc R . .
C18 C 0.64705(17) 0.31897(15) 0.11264(10) 0.0316(3) Uani 1 1 d . . .
H18 H 0.7250 0.3508 0.1706 0.038 Uiso 1 1 calc R . .
C19 C 0.50533(17) 0.21159(16) 0.10685(10) 0.0324(3) Uani 1 1 d . . .
C20 C 1.20628(15) 0.23849(14) 0.56490(10) 0.0253(3) Uani 1 1 d . . .
C21 C 1.27775(16) 0.10849(15) 0.54619(10) 0.0280(3) Uani 1 1 d . . .
H21 H 1.2282 0.0211 0.4943 0.034 Uiso 1 1 calc R . .
C22 C 1.42065(16) 0.10674(16) 0.60310(10) 0.0304(3) Uani 1 1 d . . .
H22 H 1.4672 0.0174 0.5907 0.037 Uiso 1 1 calc R . .
C23 C 1.49573(16) 0.23354(16) 0.67745(10) 0.0311(3) Uani 1 1 d . . .
H23 H 1.5925 0.2309 0.7170 0.037 Uiso 1 1 calc R . .
C24 C 1.42939(16) 0.36541(16) 0.69443(10) 0.0307(3) Uani 1 1 d . . .
H24 H 1.4826 0.4539 0.7442 0.037 Uiso 1 1 calc R . .
C25 C 1.28606(15) 0.36746(15) 0.63872(10) 0.0281(3) Uani 1 1 d . . .
H25 H 1.2411 0.4577 0.6507 0.034 Uiso 1 1 calc R . .
C26 C 0.90833(15) 0.37918(14) 0.64899(9) 0.0246(3) Uani 1 1 d . . .
C27 C 0.94324(16) 0.31233(15) 0.72383(10) 0.0292(3) Uani 1 1 d . . .
H27 H 0.9755 0.2160 0.7078 0.035 Uiso 1 1 calc R . .
C28 C 0.93093(17) 0.38605(17) 0.82091(10) 0.0360(3) Uani 1 1 d . . .
H28 H 0.9535 0.3396 0.8714 0.043 Uiso 1 1 calc R . .
C29 C 0.88582(18) 0.52778(18) 0.84537(11) 0.0381(4) Uani 1 1 d . . .
H29 H 0.8788 0.5785 0.9125 0.046 Uiso 1 1 calc R . .
C30 C 0.85119(17) 0.59494(17) 0.77200(11) 0.0357(3) Uani 1 1 d . . .
H30 H 0.8213 0.6923 0.7887 0.043 Uiso 1 1 calc R . .
C31 C 0.86010(15) 0.52042(15) 0.67439(10) 0.0290(3) Uani 1 1 d . . .
H31 H 0.8331 0.5657 0.6239 0.035 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2150(15) . ?
C1 C5 1.4990(18) . ?
C1 C2 1.4995(19) . ?
C2 C3 1.3643(17) . ?
C2 C20 1.4697(18) . ?
C3 C26 1.4738(18) . ?
C3 C4 1.4910(18) . ?
C4 C9 1.3858(18) . ?
C4 C5 1.3969(17) . ?
C5 C6 1.3677(19) . ?
C6 C7 1.4147(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.3867(19) . ?
C7 C10 1.492(2) . ?
C8 C9 1.3947(19) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.372(2) . ?
C10 C19 1.424(2) . ?
C11 C12 1.401(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.414(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.416(2) . ?
C14 C19 1.425(2) . ?
C15 C16 1.351(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.394(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.362(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.431(2) . ?
C18 H18 0.9500 . ?
C20 C25 1.3981(19) . ?
C20 C21 1.3998(17) . ?
C21 C22 1.3866(19) . ?
C21 H21 0.9500 . ?
C22 C23 1.379(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.3920(19) . ?
C23 H23 0.9500 . ?
C24 C25 1.3820(19) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C31 1.3963(17) . ?
C26 C27 1.3973(18) . ?
C27 C28 1.379(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.389(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.381(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.3803(19) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?

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
O1 C1 C5 126.60(13) . . ?
O1 C1 C2 127.27(12) . . ?
C5 C1 C2 106.13(11) . . ?
C3 C2 C20 128.18(12) . . ?
C3 C2 C1 108.02(12) . . ?
C20 C2 C1 123.78(11) . . ?
C2 C3 C26 127.19(12) . . ?
C2 C3 C4 109.90(11) . . ?
C26 C3 C4 122.88(11) . . ?
C9 C4 C5 119.64(12) . . ?
C9 C4 C3 131.81(12) . . ?
C5 C4 C3 108.40(11) . . ?
C6 C5 C4 122.12(12) . . ?
C6 C5 C1 130.27(12) . . ?
C4 C5 C1 107.48(11) . . ?
C5 C6 C7 118.91(12) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 118.61(13) . . ?
C8 C7 C10 120.19(12) . . ?
C6 C7 C10 121.13(12) . . ?
C7 C8 C9 122.30(12) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 H8 118.9 . . ?
C4 C9 C8 118.39(12) . . ?
C4 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C11 C10 C19 119.20(13) . . ?
C11 C10 C7 119.97(13) . . ?
C19 C10 C7 120.83(13) . . ?
C10 C11 C12 122.26(14) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C13 C12 C11 119.56(15) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.40(14) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C15 121.97(14) . . ?
C13 C14 C19 119.58(14) . . ?
C15 C14 C19 118.45(14) . . ?
C16 C15 C14 121.88(15) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C17 119.61(15) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 121.79(15) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C17 C18 C19 119.93(14) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C10 C19 C14 118.99(14) . . ?
C10 C19 C18 122.64(13) . . ?
C14 C19 C18 118.34(13) . . ?
C25 C20 C21 118.51(12) . . ?
C25 C20 C2 120.60(11) . . ?
C21 C20 C2 120.89(12) . . ?
C22 C21 C20 120.27(13) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 120.56(12) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 119.81(13) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C25 C24 C23 119.92(13) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C20 120.86(12) . . ?
C24 C25 H25 119.6 . . ?
C20 C25 H25 119.6 . . ?
C31 C26 C27 118.85(12) . . ?
C31 C26 C3 120.17(11) . . ?
C27 C26 C3 120.99(11) . . ?
C28 C27 C26 120.09(12) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C29 120.45(13) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C30 C29 C28 119.94(13) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C31 C30 C29 119.90(13) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 C26 120.75(13) . . ?
C30 C31 H31 119.6 . . ?
C26 C31 H31 119.6 . . ?

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 -177.50(13) . . . . ?
C5 C1 C2 C3 2.06(14) . . . . ?
O1 C1 C2 C20 4.0(2) . . . . ?
C5 C1 C2 C20 -176.43(11) . . . . ?
C20 C2 C3 C26 -4.3(2) . . . . ?
C1 C2 C3 C26 177.25(11) . . . . ?
C20 C2 C3 C4 177.60(12) . . . . ?
C1 C2 C3 C4 -0.81(14) . . . . ?
C2 C3 C4 C9 174.57(13) . . . . ?
C26 C3 C4 C9 -3.6(2) . . . . ?
C2 C3 C4 C5 -0.85(14) . . . . ?
C26 C3 C4 C5 -179.02(11) . . . . ?
C9 C4 C5 C6 2.24(19) . . . . ?
C3 C4 C5 C6 178.32(12) . . . . ?
C9 C4 C5 C1 -173.96(11) . . . . ?
C3 C4 C5 C1 2.12(14) . . . . ?
O1 C1 C5 C6 1.2(2) . . . . ?
C2 C1 C5 C6 -178.34(13) . . . . ?
O1 C1 C5 C4 176.99(13) . . . . ?
C2 C1 C5 C4 -2.57(14) . . . . ?
C4 C5 C6 C7 -1.5(2) . . . . ?
C1 C5 C6 C7 173.73(13) . . . . ?
C5 C6 C7 C8 -0.21(19) . . . . ?
C5 C6 C7 C10 -177.28(12) . . . . ?
C6 C7 C8 C9 1.2(2) . . . . ?
C10 C7 C8 C9 178.32(13) . . . . ?
C5 C4 C9 C8 -1.18(19) . . . . ?
C3 C4 C9 C8 -176.19(13) . . . . ?
C7 C8 C9 C4 -0.5(2) . . . . ?
C8 C7 C10 C11 -61.41(18) . . . . ?
C6 C7 C10 C11 115.61(15) . . . . ?
C8 C7 C10 C19 117.87(15) . . . . ?
C6 C7 C10 C19 -65.11(17) . . . . ?
C19 C10 C11 C12 0.6(2) . . . . ?
C7 C10 C11 C12 179.85(12) . . . . ?
C10 C11 C12 C13 -1.2(2) . . . . ?
C11 C12 C13 C14 0.6(2) . . . . ?
C12 C13 C14 C15 -179.15(14) . . . . ?
C12 C13 C14 C19 0.6(2) . . . . ?
C13 C14 C15 C16 179.31(14) . . . . ?
C19 C14 C15 C16 -0.5(2) . . . . ?
C14 C15 C16 C17 0.4(2) . . . . ?
C15 C16 C17 C18 0.1(2) . . . . ?
C16 C17 C18 C19 -0.4(2) . . . . ?
C11 C10 C19 C14 0.68(19) . . . . ?
C7 C10 C19 C14 -178.61(11) . . . . ?
C11 C10 C19 C18 179.00(12) . . . . ?
C7 C10 C19 C18 -0.29(19) . . . . ?
C13 C14 C19 C10 -1.26(19) . . . . ?
C15 C14 C19 C10 178.51(12) . . . . ?
C13 C14 C19 C18 -179.65(12) . . . . ?
C15 C14 C19 C18 0.12(18) . . . . ?
C17 C18 C19 C10 -178.03(13) . . . . ?
C17 C18 C19 C14 0.30(19) . . . . ?
C3 C2 C20 C25 -40.30(19) . . . . ?
C1 C2 C20 C25 137.88(13) . . . . ?
C3 C2 C20 C21 138.60(14) . . . . ?
C1 C2 C20 C21 -43.22(18) . . . . ?
C25 C20 C21 C22 2.93(19) . . . . ?
C2 C20 C21 C22 -175.99(11) . . . . ?
C20 C21 C22 C23 -1.24(19) . . . . ?
C21 C22 C23 C24 -1.2(2) . . . . ?
C22 C23 C24 C25 1.9(2) . . . . ?
C23 C24 C25 C20 -0.2(2) . . . . ?
C21 C20 C25 C24 -2.23(19) . . . . ?
C2 C20 C25 C24 176.70(12) . . . . ?
C2 C3 C26 C31 131.24(14) . . . . ?
C4 C3 C26 C31 -50.93(17) . . . . ?
C2 C3 C26 C27 -48.55(19) . . . . ?
C4 C3 C26 C27 129.28(13) . . . . ?
C31 C26 C27 C28 -0.44(19) . . . . ?
C3 C26 C27 C28 179.35(12) . . . . ?
C26 C27 C28 C29 -0.8(2) . . . . ?
C27 C28 C29 C30 0.7(2) . . . . ?
C28 C29 C30 C31 0.6(2) . . . . ?
C29 C30 C31 C26 -1.8(2) . . . . ?
C27 C26 C31 C30 1.76(19) . . . . ?
C3 C26 C31 C30 -178.03(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.038
