# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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 1993085'
loop_
_audit_author_name
_audit_author_address
'Daisuke Uraguchi'
;Nagoya University
Japan
;
_audit_update_record             
;
2020-03-27 deposited with the CCDC.	2021-01-11 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            'C23 H16 O'
_chemical_formula_weight         308.36

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/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                   9.3347(13)
_cell_length_b                   10.0778(14)
_cell_length_c                   16.957(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.582(3)
_cell_angle_gamma                90
_cell_volume                     1562.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3449
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            11456
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.008
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2875
_reflns_number_gt                2378
_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)+(0.0324P)²+0.6090P] 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         2875
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0765
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
O1 O -0.06315(11) 0.01394(11) 0.37214(6) 0.0305(3) Uani 1 1 d . . . . .
C2 C 0.36106(14) 0.13680(13) 0.42644(8) 0.0204(3) Uani 1 1 d . . . . .
C3 C -0.12614(15) -0.10092(14) 0.20631(8) 0.0230(3) Uani 1 1 d . . . . .
H1 H -0.0642 -0.1735 0.2259 0.028 Uiso 1 1 calc R U . . .
C4 C 0.56777(15) 0.03087(13) 0.34710(8) 0.0220(3) Uani 1 1 d . . . . .
H2 H 0.6382 -0.0072 0.3205 0.026 Uiso 1 1 calc R U . . .
C5 C -0.16159(15) 0.13228(14) 0.18089(8) 0.0223(3) Uani 1 1 d . . . . .
H3 H -0.1233 0.2197 0.1817 0.027 Uiso 1 1 calc R U . . .
C6 C 0.31366(14) 0.07188(13) 0.35211(8) 0.0179(3) Uani 1 1 d . . . . .
C7 C 0.32405(14) 0.22617(14) 0.11348(8) 0.0218(3) Uani 1 1 d . . . . .
H4 H 0.3844 0.3026 0.1160 0.026 Uiso 1 1 calc R U . . .
C8 C 0.05702(14) 0.06722(14) 0.38096(8) 0.0211(3) Uani 1 1 d . . . . .
C9 C 0.09020(14) 0.05341(13) 0.24057(8) 0.0184(3) Uani 1 1 d . . . . .
C10 C 0.15423(14) 0.05804(13) 0.32019(8) 0.0186(3) Uani 1 1 d . . . . .
C11 C 0.25643(14) 0.19652(13) 0.17671(8) 0.0194(3) Uani 1 1 d . . . . .
H5 H 0.2706 0.2529 0.2225 0.023 Uiso 1 1 calc R U . . .
C12 C -0.06940(14) 0.02723(13) 0.21060(8) 0.0189(3) Uani 1 1 d . . . . .
C13 C 0.16754(14) 0.08452(13) 0.17386(8) 0.0183(3) Uani 1 1 d . . . . .
C14 C 0.14482(15) 0.00563(14) 0.10487(8) 0.0225(3) Uani 1 1 d . . . . .
H6 H 0.0815 -0.0689 0.1010 0.027 Uiso 1 1 calc R U . . .
C15 C 0.21395(15) 0.03513(14) 0.04171(8) 0.0244(3) Uani 1 1 d . . . . .
H7 H 0.1992 -0.0200 -0.0046 0.029 Uiso 1 1 calc R U . . .
C16 C -0.36449(15) -0.01783(16) 0.14618(8) 0.0262(3) Uani 1 1 d . . . . .
H8 H -0.4652 -0.0332 0.1248 0.031 Uiso 1 1 calc R U . . .
C17 C -0.30886(15) 0.11013(15) 0.15010(9) 0.0261(3) Uani 1 1 d . . . . .
H9 H -0.3717 0.1827 0.1317 0.031 Uiso 1 1 calc R U . . .
C18 C 0.30405(15) 0.14466(14) 0.04634(8) 0.0232(3) Uani 1 1 d . . . . .
H10 H 0.3524 0.1642 0.0035 0.028 Uiso 1 1 calc R U . . .
C19 C 0.42010(14) 0.01680(13) 0.31439(8) 0.0201(3) Uani 1 1 d . . . . .
H11 H 0.3906 -0.0310 0.2656 0.024 Uiso 1 1 calc R U . . .
C20 C 0.51031(15) 0.15206(14) 0.45812(9) 0.0236(3) Uani 1 1 d . . . . .
H12 H 0.5412 0.1985 0.5074 0.028 Uiso 1 1 calc R U . . .
C21 C -0.27268(15) -0.12303(15) 0.17354(8) 0.0249(3) Uani 1 1 d . . . . .
H13 H -0.3102 -0.2109 0.1699 0.030 Uiso 1 1 calc R U . . .
C22 C 0.61345(15) 0.10028(14) 0.41847(9) 0.0239(3) Uani 1 1 d . . . . .
H14 H 0.7148 0.1121 0.4399 0.029 Uiso 1 1 calc R U . . .
C23 C 0.11303(15) 0.14775(14) 0.45199(8) 0.0250(3) Uani 1 1 d . . . . .
H15 H 0.0475 0.1781 0.4843 0.030 Uiso 1 1 calc R U . . .
C24 C 0.25460(16) 0.17974(14) 0.47256(9) 0.0247(3) Uani 1 1 d . . . . .
H16 H 0.2866 0.2326 0.5192 0.030 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
O1 C8 1.2254(17) . ?
C2 C20 1.3974(19) . ?
C2 C6 1.4103(19) . ?
C2 C24 1.4486(19) . ?
C3 C21 1.387(2) . ?
C3 C12 1.3922(19) . ?
C3 H1 0.9500 . ?
C4 C19 1.3859(19) . ?
C4 C22 1.389(2) . ?
C4 H2 0.9500 . ?
C5 C17 1.387(2) . ?
C5 C12 1.3932(19) . ?
C5 H3 0.9500 . ?
C6 C19 1.3998(18) . ?
C6 C10 1.4845(18) . ?
C7 C11 1.3817(19) . ?
C7 C18 1.386(2) . ?
C7 H4 0.9500 . ?
C8 C23 1.459(2) . ?
C8 C10 1.5063(18) . ?
C9 C10 1.3632(19) . ?
C9 C13 1.4923(18) . ?
C9 C12 1.4979(18) . ?
C11 C13 1.3960(18) . ?
C11 H5 0.9500 . ?
C13 C14 1.3950(19) . ?
C14 C15 1.389(2) . ?
C14 H6 0.9500 . ?
C15 C18 1.380(2) . ?
C15 H7 0.9500 . ?
C16 C21 1.383(2) . ?
C16 C17 1.387(2) . ?
C16 H8 0.9500 . ?
C17 H9 0.9500 . ?
C18 H10 0.9500 . ?
C19 H11 0.9500 . ?
C20 C22 1.382(2) . ?
C20 H12 0.9500 . ?
C21 H13 0.9500 . ?
C22 H14 0.9500 . ?
C23 C24 1.337(2) . ?
C23 H15 0.9500 . ?
C24 H16 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
C20 C2 C6 120.29(12) . . ?
C20 C2 C24 119.91(13) . . ?
C6 C2 C24 119.67(12) . . ?
C21 C3 C12 120.27(13) . . ?
C21 C3 H1 119.9 . . ?
C12 C3 H1 119.9 . . ?
C19 C4 C22 120.46(13) . . ?
C19 C4 H2 119.8 . . ?
C22 C4 H2 119.8 . . ?
C17 C5 C12 120.49(13) . . ?
C17 C5 H3 119.8 . . ?
C12 C5 H3 119.8 . . ?
C19 C6 C2 117.92(12) . . ?
C19 C6 C10 123.22(12) . . ?
C2 C6 C10 118.76(11) . . ?
C11 C7 C18 120.14(13) . . ?
C11 C7 H4 119.9 . . ?
C18 C7 H4 119.9 . . ?
O1 C8 C23 120.79(12) . . ?
O1 C8 C10 123.50(12) . . ?
C23 C8 C10 115.69(12) . . ?
C10 C9 C13 124.12(12) . . ?
C10 C9 C12 123.40(12) . . ?
C13 C9 C12 112.30(11) . . ?
C9 C10 C6 124.91(12) . . ?
C9 C10 C8 118.37(12) . . ?
C6 C10 C8 116.25(11) . . ?
C7 C11 C13 120.59(12) . . ?
C7 C11 H5 119.7 . . ?
C13 C11 H5 119.7 . . ?
C3 C12 C5 119.02(12) . . ?
C3 C12 C9 121.54(12) . . ?
C5 C12 C9 119.27(12) . . ?
C14 C13 C11 118.63(12) . . ?
C14 C13 C9 120.05(12) . . ?
C11 C13 C9 121.22(12) . . ?
C15 C14 C13 120.58(13) . . ?
C15 C14 H6 119.7 . . ?
C13 C14 H6 119.7 . . ?
C18 C15 C14 119.96(13) . . ?
C18 C15 H7 120.0 . . ?
C14 C15 H7 120.0 . . ?
C21 C16 C17 119.71(13) . . ?
C21 C16 H8 120.1 . . ?
C17 C16 H8 120.1 . . ?
C5 C17 C16 120.06(13) . . ?
C5 C17 H9 120.0 . . ?
C16 C17 H9 120.0 . . ?
C15 C18 C7 120.05(13) . . ?
C15 C18 H10 120.0 . . ?
C7 C18 H10 120.0 . . ?
C4 C19 C6 121.12(13) . . ?
C4 C19 H11 119.4 . . ?
C6 C19 H11 119.4 . . ?
C22 C20 C2 120.63(13) . . ?
C22 C20 H12 119.7 . . ?
C2 C20 H12 119.7 . . ?
C16 C21 C3 120.39(14) . . ?
C16 C21 H13 119.8 . . ?
C3 C21 H13 119.8 . . ?
C20 C22 C4 119.47(13) . . ?
C20 C22 H14 120.3 . . ?
C4 C22 H14 120.3 . . ?
C24 C23 C8 121.40(13) . . ?
C24 C23 H15 119.3 . . ?
C8 C23 H15 119.3 . . ?
C23 C24 C2 122.44(13) . . ?
C23 C24 H16 118.8 . . ?
C2 C24 H16 118.8 . . ?

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
C20 C2 C6 C19 3.92(19) . . . . ?
C24 C2 C6 C19 -171.91(12) . . . . ?
C20 C2 C6 C10 -179.74(12) . . . . ?
C24 C2 C6 C10 4.43(19) . . . . ?
C13 C9 C10 C6 -10.9(2) . . . . ?
C12 C9 C10 C6 174.34(12) . . . . ?
C13 C9 C10 C8 160.97(12) . . . . ?
C12 C9 C10 C8 -13.81(19) . . . . ?
C19 C6 C10 C9 -33.9(2) . . . . ?
C2 C6 C10 C9 149.96(13) . . . . ?
C19 C6 C10 C8 154.08(12) . . . . ?
C2 C6 C10 C8 -22.05(18) . . . . ?
O1 C8 C10 C9 34.22(19) . . . . ?
C23 C8 C10 C9 -144.27(13) . . . . ?
O1 C8 C10 C6 -153.22(13) . . . . ?
C23 C8 C10 C6 28.29(17) . . . . ?
C18 C7 C11 C13 0.0(2) . . . . ?
C21 C3 C12 C5 -0.6(2) . . . . ?
C21 C3 C12 C9 -175.89(12) . . . . ?
C17 C5 C12 C3 2.3(2) . . . . ?
C17 C5 C12 C9 177.69(12) . . . . ?
C10 C9 C12 C3 -80.46(17) . . . . ?
C13 C9 C12 C3 104.22(14) . . . . ?
C10 C9 C12 C5 104.23(16) . . . . ?
C13 C9 C12 C5 -71.09(16) . . . . ?
C7 C11 C13 C14 -1.97(19) . . . . ?
C7 C11 C13 C9 -178.14(12) . . . . ?
C10 C9 C13 C14 137.92(14) . . . . ?
C12 C9 C13 C14 -46.80(17) . . . . ?
C10 C9 C13 C11 -45.97(19) . . . . ?
C12 C9 C13 C11 129.32(13) . . . . ?
C11 C13 C14 C15 2.5(2) . . . . ?
C9 C13 C14 C15 178.73(12) . . . . ?
C13 C14 C15 C18 -1.1(2) . . . . ?
C12 C5 C17 C16 -2.2(2) . . . . ?
C21 C16 C17 C5 0.4(2) . . . . ?
C14 C15 C18 C7 -0.8(2) . . . . ?
C11 C7 C18 C15 1.4(2) . . . . ?
C22 C4 C19 C6 0.1(2) . . . . ?
C2 C6 C19 C4 -3.0(2) . . . . ?
C10 C6 C19 C4 -179.11(12) . . . . ?
C6 C2 C20 C22 -2.0(2) . . . . ?
C24 C2 C20 C22 173.77(13) . . . . ?
C17 C16 C21 C3 1.3(2) . . . . ?
C12 C3 C21 C16 -1.2(2) . . . . ?
C2 C20 C22 C4 -0.9(2) . . . . ?
C19 C4 C22 C20 1.9(2) . . . . ?
O1 C8 C23 C24 163.65(14) . . . . ?
C10 C8 C23 C24 -17.81(19) . . . . ?
C8 C23 C24 C2 -0.2(2) . . . . ?
C20 C2 C24 C23 -168.36(14) . . . . ?
C6 C2 C24 C23 7.5(2) . . . . ?

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.174
_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_2H
_database_code_depnum_ccdc_archive 'CCDC 1993086'
loop_
_audit_author_name
_audit_author_address
'Daisuke Uraguchi'
;Nagoya University
Japan
;
_audit_update_record             
;
2020-03-27 deposited with the CCDC.	2021-01-11 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            'C26 H20 O'
_chemical_formula_weight         348.42

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                   10.294(3)
_cell_length_b                   16.632(4)
_cell_length_c                   11.319(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.274(2)
_cell_angle_gamma                90
_cell_volume                     1793.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    4140
_cell_measurement_theta_min      6.256
_cell_measurement_theta_max      54.971

_exptl_crystal_description       Block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            30752
_diffrn_reflns_av_unetI/netI     0.0058
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.128
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3334
_reflns_number_gt                3138
_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)+(0.0385P)²+0.7512P] 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         3334
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0849
_refine_ls_wR_factor_gt          0.0833
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
O1 O 0.42213(8) 0.17950(5) 0.67444(8) 0.0264(2) Uani 1 1 d . . . . .
C2 C 0.96442(11) 0.19643(6) 0.77893(10) 0.0166(2) Uani 1 1 d . . . . .
C3 C 0.86594(11) 0.13675(6) 0.71638(10) 0.0166(2) Uani 1 1 d . . . . .
C4 C 0.77832(11) 0.29710(6) 0.71189(10) 0.0192(2) Uani 1 1 d . . . . .
C5 C 0.47097(11) 0.11476(7) 0.66079(10) 0.0201(2) Uani 1 1 d . . . . .
C6 C 0.66474(11) 0.01520(6) 0.75875(10) 0.0188(2) Uani 1 1 d . . . . .
C7 C 0.56490(11) 0.25794(7) 0.53776(11) 0.0228(2) Uani 1 1 d . . . . .
H1 H 0.5011 0.2173 0.4914 0.027 Uiso 1 1 calc R U . . .
C8 C 0.71563(11) 0.15290(6) 0.69223(10) 0.0172(2) Uani 1 1 d . . . . .
C9 C 0.68017(11) 0.23756(6) 0.64697(10) 0.0183(2) Uani 1 1 d . . . . .
C10 C 0.62531(11) 0.09738(6) 0.70590(10) 0.0182(2) Uani 1 1 d . . . . .
C11 C 0.75313(13) 0.37617(7) 0.66855(11) 0.0253(3) Uani 1 1 d . . . . .
H2 H 0.8177 0.4171 0.7126 0.030 Uiso 1 1 calc R U . . .
C12 C 0.79199(12) -0.00185(7) 0.85817(11) 0.0240(2) Uani 1 1 d . . . . .
H3 H 0.8582 0.0401 0.8930 0.029 Uiso 1 1 calc R U . . .
C13 C 1.14319(12) 0.11913(7) 0.74086(11) 0.0235(2) Uani 1 1 d . . . . .
H4 H 1.2384 0.1128 0.7505 0.028 Uiso 1 1 calc R U . . .
C14 C 0.90707(11) 0.06992(6) 0.66453(10) 0.0190(2) Uani 1 1 d . . . . .
H5 H 0.8401 0.0298 0.6215 0.023 Uiso 1 1 calc R U . . .
C15 C 1.04495(12) 0.06183(7) 0.67548(11) 0.0215(2) Uani 1 1 d . . . . .
H6 H 1.0721 0.0170 0.6381 0.026 Uiso 1 1 calc R U . . .
C16 C 0.59936(12) -0.12516(7) 0.76256(11) 0.0242(2) Uani 1 1 d . . . . .
H7 H 0.5331 -0.1673 0.7299 0.029 Uiso 1 1 calc R U . . .
C17 C 1.02221(12) 0.33763(7) 0.86711(12) 0.0259(3) Uani 1 1 d . . . . .
H8 H 1.0479 0.3531 0.7953 0.039 Uiso 1 1 calc R U . . .
H9 H 1.1055 0.3178 0.9374 0.039 Uiso 1 1 calc R U . . .
H10 H 0.9845 0.3845 0.8959 0.039 Uiso 1 1 calc R U . . .
C18 C 0.56544(11) -0.04743(7) 0.71397(10) 0.0197(2) Uani 1 1 d . . . . .
C19 C 0.72807(13) -0.14134(7) 0.85758(12) 0.0282(3) Uani 1 1 d . . . . .
H11 H 0.7514 -0.1946 0.8890 0.034 Uiso 1 1 calc R U . . .
C20 C 1.10327(11) 0.18587(7) 0.79238(10) 0.0211(2) Uani 1 1 d . . . . .
H12 H 1.1716 0.2248 0.8374 0.025 Uiso 1 1 calc R U . . .
C21 C 0.87228(12) 0.24990(7) 0.94019(11) 0.0231(2) Uani 1 1 d . . . . .
H13 H 0.8343 0.2976 0.9667 0.035 Uiso 1 1 calc R U . . .
H14 H 0.9565 0.2315 1.0110 0.035 Uiso 1 1 calc R U . . .
H15 H 0.8017 0.2070 0.9161 0.035 Uiso 1 1 calc R U . . .
C22 C 0.91083(11) 0.27133(6) 0.82453(10) 0.0192(2) Uani 1 1 d . . . . .
C23 C 0.54240(13) 0.33696(8) 0.49610(12) 0.0284(3) Uani 1 1 d . . . . .
H16 H 0.4629 0.3504 0.4220 0.034 Uiso 1 1 calc R U . . .
C24 C 0.37905(11) 0.04699(7) 0.59792(11) 0.0226(2) Uani 1 1 d . . . . .
H17 H 0.2865 0.0571 0.5385 0.027 Uiso 1 1 calc R U . . .
C25 C 0.63553(14) 0.39615(7) 0.56230(12) 0.0295(3) Uani 1 1 d . . . . .
H18 H 0.6190 0.4505 0.5350 0.035 Uiso 1 1 calc R U . . .
C26 C 0.42474(11) -0.02884(7) 0.62376(11) 0.0224(2) Uani 1 1 d . . . . .
H19 H 0.3635 -0.0717 0.5820 0.027 Uiso 1 1 calc R U . . .
C27 C 0.82320(13) -0.07905(8) 0.90685(12) 0.0289(3) Uani 1 1 d . . . . .
H20 H 0.9105 -0.0895 0.9746 0.035 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
O1 C5 1.2226(14) . ?
C2 C20 1.3899(16) . ?
C2 C3 1.4036(15) . ?
C2 C22 1.5292(15) . ?
C3 C14 1.3956(15) . ?
C3 C8 1.4901(15) . ?
C4 C11 1.3932(16) . ?
C4 C9 1.4066(16) . ?
C4 C22 1.5335(15) . ?
C5 C24 1.4702(15) . ?
C5 C10 1.5012(15) . ?
C6 C12 1.3947(16) . ?
C6 C18 1.4121(15) . ?
C6 C10 1.4856(15) . ?
C7 C23 1.3859(17) . ?
C7 C9 1.3926(16) . ?
C7 H1 0.9500 . ?
C8 C10 1.3601(15) . ?
C8 C9 1.4956(15) . ?
C11 C25 1.3851(18) . ?
C11 H2 0.9500 . ?
C12 C27 1.3860(17) . ?
C12 H3 0.9500 . ?
C13 C15 1.3825(16) . ?
C13 C20 1.3866(16) . ?
C13 H4 0.9500 . ?
C14 C15 1.3836(16) . ?
C14 H5 0.9500 . ?
C15 H6 0.9500 . ?
C16 C19 1.3800(17) . ?
C16 C18 1.3966(16) . ?
C16 H7 0.9500 . ?
C17 C22 1.5309(15) . ?
C17 H8 0.9800 . ?
C17 H9 0.9800 . ?
C17 H10 0.9800 . ?
C18 C26 1.4543(16) . ?
C19 C27 1.3891(18) . ?
C19 H11 0.9500 . ?
C20 H12 0.9500 . ?
C21 C22 1.5467(15) . ?
C21 H13 0.9800 . ?
C21 H14 0.9800 . ?
C21 H15 0.9800 . ?
C23 C25 1.3802(19) . ?
C23 H16 0.9500 . ?
C24 C26 1.3391(17) . ?
C24 H17 0.9500 . ?
C25 H18 0.9500 . ?
C26 H19 0.9500 . ?
C27 H20 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
C20 C2 C3 118.82(10) . . ?
C20 C2 C22 123.61(9) . . ?
C3 C2 C22 117.54(9) . . ?
C14 C3 C2 119.94(10) . . ?
C14 C3 C8 121.73(9) . . ?
C2 C3 C8 117.79(9) . . ?
C11 C4 C9 118.66(10) . . ?
C11 C4 C22 123.01(10) . . ?
C9 C4 C22 118.29(9) . . ?
O1 C5 C24 121.08(10) . . ?
O1 C5 C10 124.02(10) . . ?
C24 C5 C10 114.90(9) . . ?
C12 C6 C18 118.06(10) . . ?
C12 C6 C10 122.80(10) . . ?
C18 C6 C10 118.95(10) . . ?
C23 C7 C9 120.60(11) . . ?
C23 C7 H1 119.7 . . ?
C9 C7 H1 119.7 . . ?
C10 C8 C3 124.32(10) . . ?
C10 C8 C9 126.12(10) . . ?
C3 C8 C9 109.52(9) . . ?
C7 C9 C4 119.61(10) . . ?
C7 C9 C8 123.26(10) . . ?
C4 C9 C8 116.76(9) . . ?
C8 C10 C6 125.18(10) . . ?
C8 C10 C5 120.77(10) . . ?
C6 C10 C5 113.98(9) . . ?
C25 C11 C4 121.13(11) . . ?
C25 C11 H2 119.4 . . ?
C4 C11 H2 119.4 . . ?
C27 C12 C6 120.96(11) . . ?
C27 C12 H3 119.5 . . ?
C6 C12 H3 119.5 . . ?
C15 C13 C20 120.24(10) . . ?
C15 C13 H4 119.9 . . ?
C20 C13 H4 119.9 . . ?
C15 C14 C3 120.28(10) . . ?
C15 C14 H5 119.9 . . ?
C3 C14 H5 119.9 . . ?
C13 C15 C14 119.89(10) . . ?
C13 C15 H6 120.1 . . ?
C14 C15 H6 120.1 . . ?
C19 C16 C18 120.68(11) . . ?
C19 C16 H7 119.7 . . ?
C18 C16 H7 119.7 . . ?
C22 C17 H8 109.5 . . ?
C22 C17 H9 109.5 . . ?
H8 C17 H9 109.5 . . ?
C22 C17 H10 109.5 . . ?
H8 C17 H10 109.5 . . ?
H9 C17 H10 109.5 . . ?
C16 C18 C6 120.17(10) . . ?
C16 C18 C26 120.47(10) . . ?
C6 C18 C26 119.21(10) . . ?
C16 C19 C27 119.34(11) . . ?
C16 C19 H11 120.3 . . ?
C27 C19 H11 120.3 . . ?
C13 C20 C2 120.76(10) . . ?
C13 C20 H12 119.6 . . ?
C2 C20 H12 119.6 . . ?
C22 C21 H13 109.5 . . ?
C22 C21 H14 109.5 . . ?
H13 C21 H14 109.5 . . ?
C22 C21 H15 109.5 . . ?
H13 C21 H15 109.5 . . ?
H14 C21 H15 109.5 . . ?
C2 C22 C17 111.72(9) . . ?
C2 C22 C4 105.55(8) . . ?
C17 C22 C4 112.61(9) . . ?
C2 C22 C21 109.82(9) . . ?
C17 C22 C21 107.54(9) . . ?
C4 C22 C21 109.60(9) . . ?
C25 C23 C7 119.97(11) . . ?
C25 C23 H16 120.0 . . ?
C7 C23 H16 120.0 . . ?
C26 C24 C5 120.53(10) . . ?
C26 C24 H17 119.7 . . ?
C5 C24 H17 119.7 . . ?
C23 C25 C11 119.93(11) . . ?
C23 C25 H18 120.0 . . ?
C11 C25 H18 120.0 . . ?
C24 C26 C18 121.84(10) . . ?
C24 C26 H19 119.1 . . ?
C18 C26 H19 119.1 . . ?
C12 C27 C19 120.62(11) . . ?
C12 C27 H20 119.7 . . ?
C19 C27 H20 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
C20 C2 C3 C14 -2.58(15) . . . . ?
C22 C2 C3 C14 175.31(9) . . . . ?
C20 C2 C3 C8 -174.33(9) . . . . ?
C22 C2 C3 C8 3.55(14) . . . . ?
C14 C3 C8 C10 49.10(15) . . . . ?
C2 C3 C8 C10 -139.30(11) . . . . ?
C14 C3 C8 C9 -128.92(10) . . . . ?
C2 C3 C8 C9 42.67(12) . . . . ?
C23 C7 C9 C4 -3.17(16) . . . . ?
C23 C7 C9 C8 -175.90(10) . . . . ?
C11 C4 C9 C7 3.41(15) . . . . ?
C22 C4 C9 C7 -174.54(9) . . . . ?
C11 C4 C9 C8 176.60(10) . . . . ?
C22 C4 C9 C8 -1.35(14) . . . . ?
C10 C8 C9 C7 -48.64(16) . . . . ?
C3 C8 C9 C7 129.34(11) . . . . ?
C10 C8 C9 C4 138.44(11) . . . . ?
C3 C8 C9 C4 -43.58(12) . . . . ?
C3 C8 C10 C6 6.38(16) . . . . ?
C9 C8 C10 C6 -175.93(10) . . . . ?
C3 C8 C10 C5 -170.64(9) . . . . ?
C9 C8 C10 C5 7.06(16) . . . . ?
C12 C6 C10 C8 36.00(16) . . . . ?
C18 C6 C10 C8 -149.16(11) . . . . ?
C12 C6 C10 C5 -146.81(10) . . . . ?
C18 C6 C10 C5 28.04(14) . . . . ?
O1 C5 C10 C8 -40.92(16) . . . . ?
C24 C5 C10 C8 139.45(11) . . . . ?
O1 C5 C10 C6 141.75(11) . . . . ?
C24 C5 C10 C6 -37.88(13) . . . . ?
C9 C4 C11 C25 -1.24(17) . . . . ?
C22 C4 C11 C25 176.60(10) . . . . ?
C18 C6 C12 C27 3.47(17) . . . . ?
C10 C6 C12 C27 178.36(11) . . . . ?
C2 C3 C14 C15 0.58(15) . . . . ?
C8 C3 C14 C15 172.00(10) . . . . ?
C20 C13 C15 C14 -1.84(17) . . . . ?
C3 C14 C15 C13 1.65(16) . . . . ?
C19 C16 C18 C6 2.13(17) . . . . ?
C19 C16 C18 C26 -173.46(11) . . . . ?
C12 C6 C18 C16 -4.50(16) . . . . ?
C10 C6 C18 C16 -179.60(10) . . . . ?
C12 C6 C18 C26 171.14(10) . . . . ?
C10 C6 C18 C26 -3.95(15) . . . . ?
C18 C16 C19 C27 1.39(18) . . . . ?
C15 C13 C20 C2 -0.21(17) . . . . ?
C3 C2 C20 C13 2.41(16) . . . . ?
C22 C2 C20 C13 -175.34(10) . . . . ?
C20 C2 C22 C17 8.79(14) . . . . ?
C3 C2 C22 C17 -168.98(9) . . . . ?
C20 C2 C22 C4 131.50(10) . . . . ?
C3 C2 C22 C4 -46.27(12) . . . . ?
C20 C2 C22 C21 -110.44(11) . . . . ?
C3 C2 C22 C21 71.79(12) . . . . ?
C11 C4 C22 C2 -132.61(11) . . . . ?
C9 C4 C22 C2 45.24(12) . . . . ?
C11 C4 C22 C17 -10.47(15) . . . . ?
C9 C4 C22 C17 167.38(10) . . . . ?
C11 C4 C22 C21 109.18(12) . . . . ?
C9 C4 C22 C21 -72.97(12) . . . . ?
C9 C7 C23 C25 0.69(17) . . . . ?
O1 C5 C24 C26 -154.67(11) . . . . ?
C10 C5 C24 C26 24.97(15) . . . . ?
C7 C23 C25 C11 1.52(18) . . . . ?
C4 C11 C25 C23 -1.23(18) . . . . ?
C5 C24 C26 C18 0.00(17) . . . . ?
C16 C18 C26 C24 164.37(11) . . . . ?
C6 C18 C26 C24 -11.26(16) . . . . ?
C6 C12 C27 C19 -0.03(19) . . . . ?
C16 C19 C27 C12 -2.46(19) . . . . ?

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_2H-HBF4
_database_code_depnum_ccdc_archive 'CCDC 1993087'
loop_
_audit_author_name
_audit_author_address
'Daisuke Uraguchi'
;Nagoya University
Japan
;
_audit_update_record             
;
2020-03-27 deposited with the CCDC.	2021-01-11 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            'C26 H21 B F4 O'
_chemical_formula_weight         436.24

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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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                   7.49820(10)
_cell_length_b                   19.0172(4)
_cell_length_c                   14.6488(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.675(7)
_cell_angle_gamma                90
_cell_volume                     2059.13(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    17586
_cell_measurement_theta_min      6.12
_cell_measurement_theta_max      136.33

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   0.7492
_exptl_transmission_factor_max   1.0000
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.911
_shelx_estimated_absorpt_T_min   0.914
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7492
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID II'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22984
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.844
_diffrn_reflns_theta_max         68.165
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3738
_reflns_number_gt                2820
_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)+(0.0595P)²+0.1678P] 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         3738
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.1024
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
F1 F 0.17048(13) 0.30647(5) 0.83222(7) 0.0403(3) Uani 1 1 d . . . . .
F2 F -0.04890(14) 0.23647(6) 0.75512(8) 0.0446(3) Uani 1 1 d . . . . .
F3 F -0.11481(15) 0.34866(6) 0.79144(8) 0.0508(3) Uani 1 1 d . . . . .
F4 F -0.05580(15) 0.26632(6) 0.90411(8) 0.0456(3) Uani 1 1 d . . . . .
O1 O 0.23960(17) -0.06008(6) 0.69702(8) 0.0348(3) Uani 1 1 d . . . . .
H21 H 0.2693 -0.1024 0.6925 0.052 Uiso 1 1 calc R U . . .
C6 C -0.0319(2) 0.06932(9) 0.67233(11) 0.0253(4) Uani 1 1 d . . . . .
C7 C 0.2491(2) 0.01483(10) 1.06630(12) 0.0315(4) Uani 1 1 d . . . . .
H1 H 0.2859 -0.0179 1.1148 0.038 Uiso 1 1 calc R U . . .
C8 C 0.2441(2) -0.00638(9) 0.97348(12) 0.0277(4) Uani 1 1 d . . . . .
C9 C -0.1621(2) 0.02152(9) 0.69483(12) 0.0288(4) Uani 1 1 d . . . . .
H2 H -0.1302 -0.0099 0.7454 0.035 Uiso 1 1 calc R U . . .
C10 C 0.3663(2) 0.21890(9) 0.62400(13) 0.0311(4) Uani 1 1 d . . . . .
H3 H 0.3489 0.2478 0.5704 0.037 Uiso 1 1 calc R U . . .
C11 C -0.0760(2) 0.11543(9) 0.59589(12) 0.0254(4) Uani 1 1 d . . . . .
C12 C -0.3334(2) 0.01978(10) 0.64483(13) 0.0330(4) Uani 1 1 d . . . . .
H4 H -0.4207 -0.0123 0.6603 0.040 Uiso 1 1 calc R U . . .
C13 C 0.2023(2) 0.08150(10) 1.08779(13) 0.0323(4) Uani 1 1 d . . . . .
H5 H 0.2095 0.0951 1.1507 0.039 Uiso 1 1 calc R U . . .
C14 C 0.1411(2) 0.07367(9) 0.73021(12) 0.0246(4) Uani 1 1 d . . . . .
C15 C 0.2391(2) -0.04413(9) 0.78796(12) 0.0283(4) Uani 1 1 d . . . . .
C16 C -0.2509(2) 0.11232(9) 0.54621(13) 0.0316(4) Uani 1 1 d . . . . .
H6 H -0.2843 0.1425 0.4944 0.038 Uiso 1 1 calc R U . . .
C17 C 0.2341(2) 0.17010(9) 0.63629(12) 0.0260(4) Uani 1 1 d . . . . .
C18 C -0.3771(2) 0.06610(10) 0.57080(13) 0.0331(4) Uani 1 1 d . . . . .
H7 H -0.4964 0.0659 0.5364 0.040 Uiso 1 1 calc R U . . .
C19 C 0.5561(2) 0.18312(10) 0.76668(13) 0.0336(4) Uani 1 1 d . . . . .
H8 H 0.6636 0.1887 0.8107 0.040 Uiso 1 1 calc R U . . .
C20 C 0.0656(2) 0.16137(9) 0.56372(12) 0.0266(4) Uani 1 1 d . . . . .
C21 C 0.4323(2) 0.13315(9) 0.77895(12) 0.0301(4) Uani 1 1 d . . . . .
H9 H 0.4562 0.1027 0.8309 0.036 Uiso 1 1 calc R U . . .
C22 C 0.2920(2) -0.09355(10) 0.85924(13) 0.0312(4) Uani 1 1 d . . . . .
H10 H 0.3256 -0.1398 0.8445 0.037 Uiso 1 1 calc R U . . .
C23 C 0.1882(2) 0.02281(9) 0.80778(12) 0.0257(4) Uani 1 1 d . . . . .
C24 C 0.1890(2) 0.04345(9) 0.90163(12) 0.0263(4) Uani 1 1 d . . . . .
C25 C 0.5225(2) 0.22599(10) 0.68842(13) 0.0346(4) Uani 1 1 d . . . . .
H11 H 0.6088 0.2607 0.6792 0.042 Uiso 1 1 calc R U . . .
C26 C 0.1358(2) 0.11133(9) 0.92587(13) 0.0293(4) Uani 1 1 d . . . . .
H12 H 0.0942 0.1445 0.8785 0.035 Uiso 1 1 calc R U . . .
C27 C 0.1436(2) 0.12988(10) 1.01680(13) 0.0323(4) Uani 1 1 d . . . . .
H13 H 0.1089 0.1759 1.0319 0.039 Uiso 1 1 calc R U . . .
C28 C 0.1242(2) 0.12142(11) 0.48064(13) 0.0362(5) Uani 1 1 d . . . . .
H14 H 0.1695 0.0747 0.5010 0.054 Uiso 1 1 calc R U . . .
H15 H 0.2199 0.1479 0.4579 0.054 Uiso 1 1 calc R U . . .
H16 H 0.0200 0.1165 0.4308 0.054 Uiso 1 1 calc R U . . .
C29 C 0.2948(2) -0.07469(9) 0.94915(13) 0.0311(4) Uani 1 1 d . . . . .
H17 H 0.3317 -0.1082 0.9967 0.037 Uiso 1 1 calc R U . . .
C30 C 0.2684(2) 0.12580(9) 0.71550(12) 0.0257(4) Uani 1 1 d . . . . .
B31 B -0.0155(3) 0.28910(11) 0.82049(14) 0.0305(5) Uani 1 1 d . . . . .
C31 C -0.0123(2) 0.23361(10) 0.53028(14) 0.0381(5) Uani 1 1 d . . . . .
H18 H -0.1180 0.2270 0.4817 0.057 Uiso 1 1 calc R U . . .
H19 H 0.0799 0.2607 0.5054 0.057 Uiso 1 1 calc R U . . .
H20 H -0.0484 0.2591 0.5824 0.057 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
F1 B31 1.415(2) . ?
F2 B31 1.379(2) . ?
F3 B31 1.383(2) . ?
F4 B31 1.380(2) . ?
O1 C15 1.367(2) . ?
O1 H21 0.8400 . ?
C6 C9 1.413(2) . ?
C6 C11 1.417(2) . ?
C6 C14 1.428(2) . ?
C7 C13 1.367(3) . ?
C7 C8 1.413(2) . ?
C7 H1 0.9500 . ?
C8 C29 1.416(2) . ?
C8 C24 1.425(2) . ?
C9 C12 1.368(2) . ?
C9 H2 0.9500 . ?
C10 C25 1.382(2) . ?
C10 C17 1.392(2) . ?
C10 H3 0.9500 . ?
C11 C16 1.390(2) . ?
C11 C20 1.510(2) . ?
C12 C18 1.393(2) . ?
C12 H4 0.9500 . ?
C13 C27 1.403(3) . ?
C13 H5 0.9500 . ?
C14 C30 1.418(2) . ?
C14 C23 1.489(2) . ?
C15 C23 1.374(2) . ?
C15 C22 1.411(2) . ?
C16 C18 1.383(2) . ?
C16 H6 0.9500 . ?
C17 C30 1.422(2) . ?
C17 C20 1.517(2) . ?
C18 H7 0.9500 . ?
C19 C21 1.361(2) . ?
C19 C25 1.395(2) . ?
C19 H8 0.9500 . ?
C20 C31 1.540(2) . ?
C20 C28 1.559(2) . ?
C21 C30 1.418(2) . ?
C21 H9 0.9500 . ?
C22 C29 1.362(3) . ?
C22 H10 0.9500 . ?
C23 C24 1.429(2) . ?
C24 C26 1.414(2) . ?
C25 H11 0.9500 . ?
C26 C27 1.370(2) . ?
C26 H12 0.9500 . ?
C27 H13 0.9500 . ?
C28 H14 0.9800 . ?
C28 H15 0.9800 . ?
C28 H16 0.9800 . ?
C29 H17 0.9500 . ?
C31 H18 0.9800 . ?
C31 H19 0.9800 . ?
C31 H20 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O1 H21 109.5 . . ?
C9 C6 C11 120.26(15) . . ?
C9 C6 C14 119.55(16) . . ?
C11 C6 C14 120.10(15) . . ?
C13 C7 C8 121.35(17) . . ?
C13 C7 H1 119.3 . . ?
C8 C7 H1 119.3 . . ?
C7 C8 C29 122.64(16) . . ?
C7 C8 C24 118.60(16) . . ?
C29 C8 C24 118.76(16) . . ?
C12 C9 C6 120.94(17) . . ?
C12 C9 H2 119.5 . . ?
C6 C9 H2 119.5 . . ?
C25 C10 C17 121.15(17) . . ?
C25 C10 H3 119.4 . . ?
C17 C10 H3 119.4 . . ?
C16 C11 C6 117.51(15) . . ?
C16 C11 C20 120.79(16) . . ?
C6 C11 C20 121.44(14) . . ?
C9 C12 C18 118.57(16) . . ?
C9 C12 H4 120.7 . . ?
C18 C12 H4 120.7 . . ?
C7 C13 C27 119.91(17) . . ?
C7 C13 H5 120.0 . . ?
C27 C13 H5 120.0 . . ?
C30 C14 C6 121.20(15) . . ?
C30 C14 C23 119.38(14) . . ?
C6 C14 C23 119.42(15) . . ?
O1 C15 C23 117.26(15) . . ?
O1 C15 C22 121.78(16) . . ?
C23 C15 C22 120.95(16) . . ?
C18 C16 C11 121.15(17) . . ?
C18 C16 H6 119.4 . . ?
C11 C16 H6 119.4 . . ?
C10 C17 C30 117.74(15) . . ?
C10 C17 C20 120.65(15) . . ?
C30 C17 C20 121.46(15) . . ?
C16 C18 C12 121.54(16) . . ?
C16 C18 H7 119.2 . . ?
C12 C18 H7 119.2 . . ?
C21 C19 C25 118.94(16) . . ?
C21 C19 H8 120.5 . . ?
C25 C19 H8 120.5 . . ?
C11 C20 C17 113.01(14) . . ?
C11 C20 C31 111.49(14) . . ?
C17 C20 C31 110.60(14) . . ?
C11 C20 C28 105.48(14) . . ?
C17 C20 C28 106.83(13) . . ?
C31 C20 C28 109.14(15) . . ?
C19 C21 C30 121.17(17) . . ?
C19 C21 H9 119.4 . . ?
C30 C21 H9 119.4 . . ?
C29 C22 C15 119.79(17) . . ?
C29 C22 H10 120.1 . . ?
C15 C22 H10 120.1 . . ?
C15 C23 C24 120.10(16) . . ?
C15 C23 C14 118.65(15) . . ?
C24 C23 C14 121.19(15) . . ?
C26 C24 C8 118.73(16) . . ?
C26 C24 C23 122.46(16) . . ?
C8 C24 C23 118.80(15) . . ?
C10 C25 C19 121.29(17) . . ?
C10 C25 H11 119.4 . . ?
C19 C25 H11 119.4 . . ?
C27 C26 C24 120.78(17) . . ?
C27 C26 H12 119.6 . . ?
C24 C26 H12 119.6 . . ?
C26 C27 C13 120.58(17) . . ?
C26 C27 H13 119.7 . . ?
C13 C27 H13 119.7 . . ?
C20 C28 H14 109.5 . . ?
C20 C28 H15 109.5 . . ?
H14 C28 H15 109.5 . . ?
C20 C28 H16 109.5 . . ?
H14 C28 H16 109.5 . . ?
H15 C28 H16 109.5 . . ?
C22 C29 C8 121.59(16) . . ?
C22 C29 H17 119.2 . . ?
C8 C29 H17 119.2 . . ?
C14 C30 C21 120.08(16) . . ?
C14 C30 C17 120.28(15) . . ?
C21 C30 C17 119.63(15) . . ?
F2 B31 F4 110.33(16) . . ?
F2 B31 F3 110.83(15) . . ?
F4 B31 F3 110.11(16) . . ?
F2 B31 F1 108.28(15) . . ?
F4 B31 F1 108.88(14) . . ?
F3 B31 F1 108.35(16) . . ?
C20 C31 H18 109.5 . . ?
C20 C31 H19 109.5 . . ?
H18 C31 H19 109.5 . . ?
C20 C31 H20 109.5 . . ?
H18 C31 H20 109.5 . . ?
H19 C31 H20 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
C13 C7 C8 C29 178.87(15) . . . . ?
C13 C7 C8 C24 0.1(2) . . . . ?
C11 C6 C9 C12 -1.4(3) . . . . ?
C14 C6 C9 C12 175.08(16) . . . . ?
C9 C6 C11 C16 1.1(2) . . . . ?
C14 C6 C11 C16 -175.30(16) . . . . ?
C9 C6 C11 C20 -173.17(15) . . . . ?
C14 C6 C11 C20 10.4(2) . . . . ?
C6 C9 C12 C18 0.2(3) . . . . ?
C8 C7 C13 C27 1.6(2) . . . . ?
C9 C6 C14 C30 -173.46(15) . . . . ?
C11 C6 C14 C30 3.0(2) . . . . ?
C9 C6 C14 C23 6.2(2) . . . . ?
C11 C6 C14 C23 -177.37(15) . . . . ?
C6 C11 C16 C18 0.3(3) . . . . ?
C20 C11 C16 C18 174.59(16) . . . . ?
C25 C10 C17 C30 -2.5(3) . . . . ?
C25 C10 C17 C20 -178.24(16) . . . . ?
C11 C16 C18 C12 -1.5(3) . . . . ?
C9 C12 C18 C16 1.2(3) . . . . ?
C16 C11 C20 C17 167.72(15) . . . . ?
C6 C11 C20 C17 -18.2(2) . . . . ?
C16 C11 C20 C31 42.4(2) . . . . ?
C6 C11 C20 C31 -143.47(16) . . . . ?
C16 C11 C20 C28 -75.92(19) . . . . ?
C6 C11 C20 C28 98.19(18) . . . . ?
C10 C17 C20 C11 -170.23(15) . . . . ?
C30 C17 C20 C11 14.2(2) . . . . ?
C10 C17 C20 C31 -44.4(2) . . . . ?
C30 C17 C20 C31 139.97(17) . . . . ?
C10 C17 C20 C28 74.2(2) . . . . ?
C30 C17 C20 C28 -101.37(18) . . . . ?
C25 C19 C21 C30 -2.2(3) . . . . ?
O1 C15 C22 C29 177.95(15) . . . . ?
C23 C15 C22 C29 -0.7(2) . . . . ?
O1 C15 C23 C24 -178.46(14) . . . . ?
C22 C15 C23 C24 0.2(2) . . . . ?
O1 C15 C23 C14 -1.2(2) . . . . ?
C22 C15 C23 C14 177.47(15) . . . . ?
C30 C14 C23 C15 -102.29(19) . . . . ?
C6 C14 C23 C15 78.1(2) . . . . ?
C30 C14 C23 C24 74.9(2) . . . . ?
C6 C14 C23 C24 -104.72(19) . . . . ?
C7 C8 C24 C26 -2.1(2) . . . . ?
C29 C8 C24 C26 179.08(15) . . . . ?
C7 C8 C24 C23 178.37(14) . . . . ?
C29 C8 C24 C23 -0.4(2) . . . . ?
C15 C23 C24 C26 -179.17(15) . . . . ?
C14 C23 C24 C26 3.7(2) . . . . ?
C15 C23 C24 C8 0.3(2) . . . . ?
C14 C23 C24 C8 -176.85(14) . . . . ?
C17 C10 C25 C19 2.0(3) . . . . ?
C21 C19 C25 C10 0.4(3) . . . . ?
C8 C24 C26 C27 2.5(2) . . . . ?
C23 C24 C26 C27 -178.00(15) . . . . ?
C24 C26 C27 C13 -0.9(3) . . . . ?
C7 C13 C27 C26 -1.2(3) . . . . ?
C15 C22 C29 C8 0.6(3) . . . . ?
C7 C8 C29 C22 -178.77(16) . . . . ?
C24 C8 C29 C22 0.0(2) . . . . ?
C6 C14 C30 C21 174.17(16) . . . . ?
C23 C14 C30 C21 -5.5(2) . . . . ?
C6 C14 C30 C17 -7.0(2) . . . . ?
C23 C14 C30 C17 173.39(15) . . . . ?
C19 C21 C30 C14 -179.52(16) . . . . ?
C19 C21 C30 C17 1.6(3) . . . . ?
C10 C17 C30 C14 -178.11(16) . . . . ?
C20 C17 C30 C14 -2.4(2) . . . . ?
C10 C17 C30 C21 0.8(2) . . . . ?
C20 C17 C30 C21 176.46(15) . . . . ?

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.049

