# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_qq
_database_code_depnum_ccdc_archive 'CCDC 1558337'
_audit_update_record             
;
2018-05-10 deposited with the CCDC.
2018-05-28 downloaded from the CCDC.
;
_audit_creation_date             2018-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C36 H27 B F2 O3'
_chemical_formula_sum            'C36 H27 B F2 O3'
_chemical_formula_weight         556.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.7381(14)
_cell_length_b                   13.875(2)
_cell_length_c                   13.959(2)
_cell_angle_alpha                104.267(2)
_cell_angle_beta                 107.466(2)
_cell_angle_gamma                95.873(2)
_cell_volume                     1535.8(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3815
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.2749
_cell_measurement_theta_min      2.4631
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_correction_T_min  0.9828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker;SADABS;2012
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            5397
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.005
_diffrn_reflns_theta_max         25.005
_diffrn_reflns_theta_min         1.599
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3949
_reflns_number_total             5397
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5397
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0528
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1007P)²+0.0619P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1637
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C16, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C16 \\sim C17: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.01
4.a Me refined with riding coordinates:
 C36(H36A,H36B,H36C)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C22(H22), C23(H23),
  C25(H25), C26(H26), C28(H28), C31(H31), C32(H32), C34(H34), C35(H35)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.09054(16) 0.34808(11) 0.17510(11) 0.0763(4) Uani 1 1 d . . . . .
F2 F 0.12258(17) 0.25580(10) 0.02895(10) 0.0785(4) Uani 1 1 d . . . . .
O1 O 0.34123(16) 0.30445(12) 0.18400(13) 0.0653(4) Uani 1 1 d . . . . .
O2 O 0.23643(15) 0.42601(11) 0.09310(11) 0.0597(4) Uani 1 1 d . . . . .
O3 O 0.4554(2) 0.84195(13) 0.02413(15) 0.0839(6) Uani 1 1 d . . . . .
C1 C 0.9120(3) 0.04407(15) 0.28710(16) 0.0550(5) Uani 1 1 d . . . . .
H1 H 0.8279 0.0419 0.3150 0.066 Uiso 1 1 calc R . . . .
C2 C 0.8846(3) -0.01236(17) 0.18429(19) 0.0717(7) Uani 1 1 d . . . . .
H2 H 0.7825 -0.0526 0.1443 0.086 Uiso 1 1 calc R . . . .
C3 C 1.0036(5) -0.0097(2) 0.1417(2) 0.0877(9) Uani 1 1 d . . . . .
H3 H 0.9827 -0.0460 0.0721 0.105 Uiso 1 1 calc R . . . .
C4 C 1.1566(4) 0.0471(2) 0.2017(2) 0.0987(10) Uani 1 1 d . . . . .
H4 H 1.2395 0.0487 0.1728 0.118 Uiso 1 1 calc R . . . .
C5 C 1.1867(3) 0.10148(19) 0.30426(19) 0.0751(7) Uani 1 1 d . . . . .
H5 H 1.2914 0.1376 0.3450 0.090 Uiso 1 1 calc R . . . .
C6 C 1.0637(2) 0.10340(14) 0.34812(14) 0.0464(5) Uani 1 1 d . . . . .
C7 C 1.0998(2) 0.16427(14) 0.45961(14) 0.0436(4) Uani 1 1 d . . . . .
C8 C 1.2553(2) 0.15367(15) 0.53605(14) 0.0452(5) Uani 1 1 d . . . . .
C9 C 1.2891(3) 0.06031(17) 0.54231(19) 0.0657(6) Uani 1 1 d . . . . .
H9 H 1.2111 0.0023 0.5015 0.079 Uiso 1 1 calc R . . . .
C10 C 1.4379(3) 0.0513(2) 0.6087(2) 0.0814(7) Uani 1 1 d . . . . .
H10 H 1.4574 -0.0124 0.6131 0.098 Uiso 1 1 calc R . . . .
C11 C 1.5549(3) 0.1346(2) 0.6670(2) 0.0788(8) Uani 1 1 d . . . . .
H11 H 1.6546 0.1281 0.7108 0.095 Uiso 1 1 calc R . . . .
C12 C 1.5255(3) 0.2285(2) 0.6611(2) 0.0816(8) Uani 1 1 d . . . . .
H12 H 1.6061 0.2858 0.6998 0.098 Uiso 1 1 calc R . . . .
C13 C 1.3751(3) 0.23803(18) 0.59731(19) 0.0667(6) Uani 1 1 d . . . . .
H13 H 1.3545 0.3022 0.5957 0.080 Uiso 1 1 calc R . . . .
C14 C 1.0176(2) 0.21341(15) 0.66798(14) 0.0471(5) Uani 1 1 d . . . . .
H14 H 1.0251 0.1456 0.6466 0.057 Uiso 1 1 calc R . . . .
C15 C 1.0116(2) 0.25438(18) 0.76716(16) 0.0571(5) Uani 1 1 d . . . . .
H15 H 1.0135 0.2138 0.8113 0.069 Uiso 1 1 calc R . . . .
C16 C 1.0029(3) 0.3534(2) 0.80068(18) 0.0665(6) Uani 1 1 d . U . . .
H16 H 1.0008 0.3808 0.8681 0.080 Uiso 1 1 calc R . . . .
C17 C 0.9971(3) 0.41364(18) 0.7348(2) 0.0692(6) Uani 1 1 d . U . . .
H17 H 0.9903 0.4814 0.7576 0.083 Uiso 1 1 calc R . . . .
C18 C 1.0015(3) 0.37285(16) 0.63442(17) 0.0583(5) Uani 1 1 d . . . . .
H18 H 0.9971 0.4136 0.5902 0.070 Uiso 1 1 calc R . . . .
C19 C 1.0126(2) 0.27152(14) 0.59940(14) 0.0435(4) Uani 1 1 d . . . . .
C20 C 1.0009(2) 0.22497(14) 0.48818(14) 0.0448(4) Uani 1 1 d . . . . .
C21 C 0.8671(2) 0.25219(14) 0.40961(14) 0.0442(4) Uani 1 1 d . . . . .
C22 C 0.7081(2) 0.23975(17) 0.41216(17) 0.0575(6) Uani 1 1 d . . . . .
H22 H 0.6844 0.2108 0.4607 0.069 Uiso 1 1 calc R . . . .
C23 C 0.5859(2) 0.26945(17) 0.34414(17) 0.0580(6) Uani 1 1 d . . . . .
H23 H 0.4796 0.2575 0.3449 0.070 Uiso 1 1 calc R . . . .
C24 C 0.6194(2) 0.31728(14) 0.27405(14) 0.0441(4) Uani 1 1 d . . . . .
C25 C 0.7785(2) 0.33159(15) 0.27235(15) 0.0476(5) Uani 1 1 d . . . . .
H25 H 0.8036 0.3645 0.2269 0.057 Uiso 1 1 calc R . . . .
C26 C 0.8990(2) 0.29750(15) 0.33737(15) 0.0481(5) Uani 1 1 d . . . . .
H26 H 1.0034 0.3049 0.3329 0.058 Uiso 1 1 calc R . . . .
C27 C 0.4886(2) 0.35440(14) 0.20728(14) 0.0447(4) Uani 1 1 d . . . . .
C28 C 0.5152(2) 0.43856(15) 0.17544(15) 0.0492(5) Uani 1 1 d . . . . .
H28 H 0.6217 0.4717 0.1913 0.059 Uiso 1 1 calc R . . . .
C29 C 0.3860(2) 0.47490(15) 0.12003(13) 0.0441(4) Uani 1 1 d . . . . .
C30 C 0.4026(2) 0.56829(14) 0.09071(14) 0.0434(4) Uani 1 1 d . . . . .
C31 C 0.5551(2) 0.62886(17) 0.11606(17) 0.0572(5) Uani 1 1 d . . . . .
H31 H 0.6492 0.6081 0.1499 0.069 Uiso 1 1 calc R . . . .
C32 C 0.5679(3) 0.71825(18) 0.09190(19) 0.0662(6) Uani 1 1 d . . . . .
H32 H 0.6705 0.7575 0.1088 0.079 Uiso 1 1 calc R . . . .
C33 C 0.4288(2) 0.75091(16) 0.04227(17) 0.0565(5) Uani 1 1 d . . . . .
C34 C 0.2769(2) 0.69156(17) 0.01439(16) 0.0534(5) Uani 1 1 d . . . . .
H34 H 0.1833 0.7125 -0.0199 0.064 Uiso 1 1 calc R . . . .
C35 C 0.2653(2) 0.60120(16) 0.03775(15) 0.0487(5) Uani 1 1 d . . . . .
H35 H 0.1627 0.5608 0.0177 0.058 Uiso 1 1 calc R . . . .
C36 C 0.3175(3) 0.8819(2) -0.0226(2) 0.0901(9) Uani 1 1 d . . . . .
H36A H 0.3540 0.9461 -0.0308 0.135 Uiso 1 1 calc R . . . .
H36B H 0.2542 0.8358 -0.0902 0.135 Uiso 1 1 calc R . . . .
H36C H 0.2513 0.8908 0.0216 0.135 Uiso 1 1 calc R . . . .
B1 B 0.1953(3) 0.33160(19) 0.12001(18) 0.0512(6) 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
F1 B1 1.364(3) . ?
F2 B1 1.358(3) . ?
O1 C27 1.303(2) . ?
O1 B1 1.465(3) . ?
O2 C29 1.307(2) . ?
O2 B1 1.488(3) . ?
O3 C33 1.359(3) . ?
O3 C36 1.424(3) . ?
C1 C2 1.390(3) . ?
C1 C6 1.384(3) . ?
C2 C3 1.345(4) . ?
C3 C4 1.377(4) . ?
C4 C5 1.374(4) . ?
C5 C6 1.387(3) . ?
C6 C7 1.496(3) . ?
C7 C8 1.502(2) . ?
C7 C20 1.343(3) . ?
C8 C9 1.375(3) . ?
C8 C13 1.384(3) . ?
C9 C10 1.390(3) . ?
C10 C11 1.356(4) . ?
C11 C12 1.370(4) . ?
C12 C13 1.389(3) . ?
C14 C15 1.380(3) . ?
C14 C19 1.390(3) . ?
C15 C16 1.356(3) . ?
C16 C17 1.380(3) . ?
C17 C18 1.390(3) . ?
C18 C19 1.394(3) . ?
C19 C20 1.495(3) . ?
C20 C21 1.496(2) . ?
C21 C22 1.395(3) . ?
C21 C26 1.391(2) . ?
C22 C23 1.373(3) . ?
C23 C24 1.391(3) . ?
C24 C25 1.392(3) . ?
C24 C27 1.469(3) . ?
C25 C26 1.377(3) . ?
C27 C28 1.370(3) . ?
C28 C29 1.383(3) . ?
C29 C30 1.458(3) . ?
C30 C31 1.395(3) . ?
C30 C35 1.394(3) . ?
C31 C32 1.366(3) . ?
C32 C33 1.387(3) . ?
C33 C34 1.378(3) . ?
C34 C35 1.373(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C27 O1 B1 122.95(15) . . ?
C29 O2 B1 123.23(15) . . ?
C33 O3 C36 118.39(18) . . ?
C6 C1 C2 120.3(2) . . ?
C3 C2 C1 121.0(2) . . ?
C2 C3 C4 119.7(2) . . ?
C5 C4 C3 120.0(3) . . ?
C4 C5 C6 121.1(2) . . ?
C1 C6 C5 117.75(19) . . ?
C1 C6 C7 122.27(18) . . ?
C5 C6 C7 119.91(18) . . ?
C6 C7 C8 115.04(16) . . ?
C20 C7 C6 122.06(17) . . ?
C20 C7 C8 122.89(17) . . ?
C9 C8 C7 121.62(18) . . ?
C9 C8 C13 117.72(19) . . ?
C13 C8 C7 120.49(18) . . ?
C8 C9 C10 121.0(2) . . ?
C11 C10 C9 120.6(2) . . ?
C10 C11 C12 119.7(2) . . ?
C11 C12 C13 119.9(2) . . ?
C8 C13 C12 121.1(2) . . ?
C15 C14 C19 121.3(2) . . ?
C16 C15 C14 120.5(2) . . ?
C15 C16 C17 120.0(2) . . ?
C16 C17 C18 119.9(2) . . ?
C17 C18 C19 120.7(2) . . ?
C14 C19 C18 117.60(18) . . ?
C14 C19 C20 121.39(17) . . ?
C18 C19 C20 120.68(17) . . ?
C7 C20 C19 124.17(17) . . ?
C7 C20 C21 122.21(17) . . ?
C19 C20 C21 113.62(16) . . ?
C22 C21 C20 120.50(16) . . ?
C26 C21 C20 121.36(16) . . ?
C26 C21 C22 117.97(17) . . ?
C23 C22 C21 121.12(17) . . ?
C22 C23 C24 120.65(18) . . ?
C23 C24 C25 118.50(17) . . ?
C23 C24 C27 119.40(16) . . ?
C25 C24 C27 122.06(16) . . ?
C26 C25 C24 120.61(17) . . ?
C25 C26 C21 121.05(17) . . ?
O1 C27 C24 115.20(16) . . ?
O1 C27 C28 121.22(17) . . ?
C28 C27 C24 123.49(16) . . ?
C27 C28 C29 120.92(17) . . ?
O2 C29 C28 119.89(17) . . ?
O2 C29 C30 115.63(16) . . ?
C28 C29 C30 124.46(16) . . ?
C31 C30 C29 121.68(16) . . ?
C35 C30 C29 120.74(16) . . ?
C35 C30 C31 117.57(17) . . ?
C32 C31 C30 120.87(18) . . ?
C31 C32 C33 120.40(19) . . ?
O3 C33 C32 115.51(18) . . ?
O3 C33 C34 124.56(19) . . ?
C34 C33 C32 119.92(19) . . ?
C35 C34 C33 119.29(18) . . ?
C34 C35 C30 121.90(17) . . ?
F1 B1 O1 109.28(17) . . ?
F1 B1 O2 107.72(19) . . ?
F2 B1 F1 110.61(17) . . ?
F2 B1 O1 109.55(19) . . ?
F2 B1 O2 108.05(17) . . ?
O1 B1 O2 111.62(15) . . ?

_platon_squeeze_details          
;

;

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_20180217_0m
_database_code_depnum_ccdc_archive 'CCDC 1832236'
_audit_update_record             
;
2018-05-10 deposited with the CCDC.
2018-05-28 downloaded from the CCDC.
;
_audit_creation_date             2018-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C39 H33 B F2 O3'
_chemical_formula_sum            'C39 H33 B F2 O3'
_chemical_formula_weight         598.46
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

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

_cell_length_a                   9.1019(6)
_cell_length_b                   10.2969(7)
_cell_length_c                   16.7245(11)
_cell_angle_alpha                101.283(5)
_cell_angle_beta                 93.743(4)
_cell_angle_gamma                90.043(4)
_cell_volume                     1533.72(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3130
_cell_measurement_temperature    173
_cell_measurement_theta_max      62.226
_cell_measurement_theta_min      2.700
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.882
_exptl_absorpt_coefficient_mu    0.714
_exptl_absorpt_correction_T_max  0.7522
_exptl_absorpt_correction_T_min  0.5976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1411 before and 0.0631 after correction. The Ratio of minimum to maximum transmission is 0.7945. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0943
_diffrn_reflns_av_unetI/netI     0.1253
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11793
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        62.657
_diffrn_reflns_theta_max         62.657
_diffrn_reflns_theta_min         4.379
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2409
_reflns_number_total             4765
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         4765
_refine_ls_number_restraints     468
_refine_ls_R_factor_all          0.1844
_refine_ls_R_factor_gt           0.0956
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0650P)²+2.8920P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1975
_refine_ls_wR_factor_ref         0.2341
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Restrained distances
 C40-C39 \\sim C37-C38
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
5. Others
 Fixed Sof: H36A(0.5) H36B(0.5) H36C(0.5) H36D(0.5) C37(0.5) H37A(0.5)
 H37B(0.5) C38(0.5) H38A(0.5) H38B(0.5) C39(0.5) H39A(0.5) H39B(0.5) C40(0.5)
 H40A(0.5) H40B(0.5) H41A(0.5) H41B(0.5) H41C(0.5) H41D(0.5) H41E(0.5) H41F(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C36(H36A,H36B), C36(H36C,H36D), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,
 H39B), C40(H40A,H40B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23),
  C25(H25), C26(H26), C28(H28), C31(H31), C32(H32), C34(H34), C35(H35)
6.c Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C), C41(H41D,H41E,H41F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.7308(4) 0.8160(3) 0.6384(2) 0.0634(11) Uani 1 1 d . U . . .
F2 F 0.5316(4) 0.7627(3) 0.5505(2) 0.0597(10) Uani 1 1 d . U . . .
O1 O 0.6366(4) 0.6035(3) 0.6167(2) 0.0454(11) Uani 1 1 d . U . . .
O2 O 0.7613(5) 0.6864(4) 0.5116(2) 0.0473(11) Uani 1 1 d . U . . .
O3 O 1.1090(5) 0.5187(4) 0.1978(3) 0.0638(13) Uani 1 1 d . U . . .
C1 C 0.6743(7) 0.0563(5) 0.8285(3) 0.0416(14) Uani 1 1 d . U . . .
C2 C 0.7353(8) 0.1811(6) 0.8482(4) 0.0547(17) Uani 1 1 d . U . . .
H2 H 0.6799 0.2532 0.8352 0.066 Uiso 1 1 calc R . . . .
C3 C 0.8726(9) 0.2054(6) 0.8859(4) 0.0577(18) Uani 1 1 d . U . . .
H3 H 0.9118 0.2931 0.8983 0.069 Uiso 1 1 calc R . . . .
C4 C 0.9549(8) 0.1018(7) 0.9060(4) 0.0581(17) Uani 1 1 d . U . . .
H4 H 1.0510 0.1182 0.9318 0.070 Uiso 1 1 calc R . . . .
C5 C 0.8968(7) -0.0257(6) 0.8884(4) 0.0524(17) Uani 1 1 d . U . . .
H5 H 0.9514 -0.0972 0.9029 0.063 Uiso 1 1 calc R . . . .
C6 C 0.7571(7) -0.0470(6) 0.8491(4) 0.0476(15) Uani 1 1 d . U . . .
H6 H 0.7171 -0.1344 0.8360 0.057 Uiso 1 1 calc R . . . .
C7 C 0.5167(8) 0.0176(6) 0.7890(4) 0.0508(15) Uani 1 1 d . U . . .
C8 C 0.4373(6) -0.0905(5) 0.8214(3) 0.0373(13) Uani 1 1 d . U . . .
C9 C 0.3982(7) -0.0620(5) 0.9017(3) 0.0417(15) Uani 1 1 d . U . . .
H9 H 0.4232 0.0222 0.9345 0.050 Uiso 1 1 calc R . . . .
C10 C 0.3250(7) -0.1517(6) 0.9342(4) 0.0531(17) Uani 1 1 d . U . . .
H10 H 0.2997 -0.1304 0.9894 0.064 Uiso 1 1 calc R . . . .
C11 C 0.2879(8) -0.2731(6) 0.8874(4) 0.065(2) Uani 1 1 d . U . . .
H11 H 0.2337 -0.3351 0.9095 0.078 Uiso 1 1 calc R . . . .
C12 C 0.3289(7) -0.3052(6) 0.8085(4) 0.0565(17) Uani 1 1 d . U . . .
H12 H 0.3065 -0.3906 0.7765 0.068 Uiso 1 1 calc R . . . .
C13 C 0.4020(7) -0.2139(5) 0.7761(3) 0.0430(15) Uani 1 1 d . U . . .
H13 H 0.4289 -0.2362 0.7212 0.052 Uiso 1 1 calc R . . . .
C14 C 0.4553(8) 0.0709(6) 0.7323(4) 0.0537(16) Uani 1 1 d . U . . .
C15 C 0.3041(7) 0.0255(6) 0.6931(3) 0.0442(14) Uani 1 1 d . U . . .
C16 C 0.1820(7) 0.0226(6) 0.7355(4) 0.0529(17) Uani 1 1 d . U . . .
H16 H 0.1896 0.0461 0.7935 0.063 Uiso 1 1 calc R . . . .
C17 C 0.0457(8) -0.0146(6) 0.6943(4) 0.0607(18) Uani 1 1 d . U . . .
H17 H -0.0394 -0.0155 0.7242 0.073 Uiso 1 1 calc R . . . .
C18 C 0.0347(9) -0.0488(6) 0.6132(5) 0.0640(19) Uani 1 1 d . U . . .
H18 H -0.0578 -0.0776 0.5859 0.077 Uiso 1 1 calc R . . . .
C19 C 0.1534(9) -0.0433(6) 0.5690(4) 0.066(2) Uani 1 1 d . U . . .
H19 H 0.1425 -0.0651 0.5110 0.079 Uiso 1 1 calc R . . . .
C20 C 0.2927(8) -0.0056(6) 0.6083(4) 0.0542(17) Uani 1 1 d . U . . .
H20 H 0.3764 -0.0015 0.5778 0.065 Uiso 1 1 calc R . . . .
C21 C 0.5294(7) 0.1803(5) 0.6991(3) 0.0479(16) Uani 1 1 d . U . . .
C22 C 0.4644(7) 0.3021(6) 0.7126(4) 0.0515(17) Uani 1 1 d . U . . .
H22 H 0.3858 0.3180 0.7478 0.062 Uiso 1 1 calc R . . . .
C23 C 0.5114(7) 0.4011(5) 0.6760(3) 0.0425(15) Uani 1 1 d . U . . .
H23 H 0.4671 0.4857 0.6874 0.051 Uiso 1 1 calc R . . . .
C24 C 0.6224(6) 0.3793(5) 0.6228(3) 0.0361(13) Uani 1 1 d . U . . .
C25 C 0.6899(7) 0.2562(5) 0.6095(3) 0.0461(16) Uani 1 1 d . U . . .
H25 H 0.7681 0.2398 0.5741 0.055 Uiso 1 1 calc R . . . .
C26 C 0.6427(8) 0.1578(6) 0.6481(3) 0.0521(17) Uani 1 1 d . U . . .
H26 H 0.6892 0.0741 0.6392 0.062 Uiso 1 1 calc R . . . .
C27 C 0.6667(6) 0.4836(5) 0.5803(3) 0.0354(13) Uani 1 1 d . U . . .
C28 C 0.7375(6) 0.4602(5) 0.5085(3) 0.0380(14) Uani 1 1 d . U . . .
H28 H 0.7527 0.3718 0.4812 0.046 Uiso 1 1 calc R . . . .
C29 C 0.7863(6) 0.5648(5) 0.4760(3) 0.0359(13) Uani 1 1 d . U . . .
C30 C 0.8714(6) 0.5485(5) 0.4044(3) 0.0343(13) Uani 1 1 d . U . . .
C31 C 0.8929(7) 0.6547(5) 0.3657(4) 0.0465(16) Uani 1 1 d . U . . .
H31 H 0.8524 0.7383 0.3872 0.056 Uiso 1 1 calc R . . . .
C32 C 0.9707(7) 0.6410(6) 0.2977(4) 0.0524(17) Uani 1 1 d . U . . .
H32 H 0.9833 0.7149 0.2724 0.063 Uiso 1 1 calc R . . . .
C33 C 1.0315(7) 0.5212(6) 0.2651(4) 0.0451(15) Uani 1 1 d . U . . .
C34 C 1.0134(7) 0.4141(5) 0.3028(3) 0.0415(14) Uani 1 1 d . U . . .
H34 H 1.0561 0.3313 0.2819 0.050 Uiso 1 1 calc R . . . .
C35 C 0.9331(7) 0.4288(5) 0.3706(3) 0.0416(15) Uani 1 1 d . U . . .
H35 H 0.9194 0.3544 0.3953 0.050 Uiso 1 1 calc R . . . .
C36 C 1.1821(9) 0.4012(6) 0.1641(4) 0.077(2) Uani 1 1 d . U . . .
H36A H 1.1172 0.3223 0.1584 0.092 Uiso 0.5 1 calc R . P A 1
H36B H 1.2728 0.3888 0.1976 0.092 Uiso 0.5 1 calc R . P A 1
H36C H 1.1065 0.3337 0.1391 0.092 Uiso 0.5 1 calc R . P B 2
H36D H 1.2355 0.3681 0.2094 0.092 Uiso 0.5 1 calc R . P B 2
C37 C 1.285(2) 0.4111(19) 0.1037(8) 0.062(4) Uani 0.5 1 d D U P C 2
H37A H 1.3578 0.3391 0.1000 0.075 Uiso 0.5 1 calc R . P C 2
H37B H 1.3380 0.4975 0.1168 0.075 Uiso 0.5 1 calc R . P C 2
C38 C 1.193(2) 0.399(2) 0.0280(11) 0.093(5) Uani 0.5 1 d D U P C 2
H38A H 1.1438 0.4834 0.0242 0.112 Uiso 0.5 1 calc R . P C 2
H38B H 1.1172 0.3283 0.0236 0.112 Uiso 0.5 1 calc R . P C 2
C39 C 1.220(2) 0.4305(17) 0.0747(11) 0.055(4) Uani 0.5 1 d D U P C 1
H39A H 1.1278 0.4416 0.0423 0.066 Uiso 0.5 1 calc R . P C 1
H39B H 1.2791 0.5134 0.0821 0.066 Uiso 0.5 1 calc R . P C 1
C40 C 1.3052(14) 0.3171(10) 0.0302(7) 0.042(3) Uani 0.5 1 d D U P C 1
H40A H 1.2490 0.2328 0.0231 0.051 Uiso 0.5 1 calc R . P C 1
H40B H 1.4013 0.3082 0.0597 0.051 Uiso 0.5 1 calc R . P C 1
C41 C 1.3258(13) 0.3552(9) -0.0519(5) 0.127(4) Uani 1 1 d . U . . .
H41A H 1.2299 0.3753 -0.0765 0.191 Uiso 0.5 1 calc GR . P C 1
H41B H 1.3701 0.2814 -0.0882 0.191 Uiso 0.5 1 calc GR . P C 1
H41C H 1.3906 0.4333 -0.0438 0.191 Uiso 0.5 1 calc GR . P C 1
H41D H 1.3982 0.4273 -0.0469 0.191 Uiso 0.5 1 calc GR . P C 2
H41E H 1.2731 0.3414 -0.1059 0.191 Uiso 0.5 1 calc GR . P C 2
H41F H 1.3764 0.2737 -0.0450 0.191 Uiso 0.5 1 calc GR . P C 2
B010 B 0.6648(8) 0.7203(6) 0.5801(4) 0.0399(16) Uani 1 1 d . 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 B010 1.352(7) . ?
F2 B010 1.382(8) . ?
O1 C27 1.303(6) . ?
O1 B010 1.481(7) . ?
O2 C29 1.304(6) . ?
O2 B010 1.477(8) . ?
O3 C33 1.362(7) . ?
O3 C36 1.417(7) . ?
C1 C2 1.370(8) . ?
C1 C6 1.389(7) . ?
C1 C7 1.557(9) . ?
C2 H2 0.9500 . ?
C2 C3 1.362(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.530(8) . ?
C7 C14 1.283(8) . ?
C8 C9 1.387(7) . ?
C8 C13 1.371(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.355(8) . ?
C10 H10 0.9500 . ?
C10 C11 1.368(8) . ?
C11 H11 0.9500 . ?
C11 C12 1.373(9) . ?
C12 H12 0.9500 . ?
C12 C13 1.366(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.519(9) . ?
C14 C21 1.525(8) . ?
C15 C16 1.360(8) . ?
C15 C20 1.388(8) . ?
C16 H16 0.9500 . ?
C16 C17 1.394(9) . ?
C17 H17 0.9500 . ?
C17 C18 1.330(9) . ?
C18 H18 0.9500 . ?
C18 C19 1.357(10) . ?
C19 H19 0.9500 . ?
C19 C20 1.407(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.372(7) . ?
C21 C26 1.372(8) . ?
C22 H22 0.9500 . ?
C22 C23 1.369(8) . ?
C23 H23 0.9500 . ?
C23 C24 1.379(7) . ?
C24 C25 1.394(7) . ?
C24 C27 1.468(7) . ?
C25 H25 0.9500 . ?
C25 C26 1.385(7) . ?
C26 H26 0.9500 . ?
C27 C28 1.380(7) . ?
C28 H28 0.9500 . ?
C28 C29 1.382(7) . ?
C29 C30 1.451(7) . ?
C30 C31 1.394(7) . ?
C30 C35 1.387(7) . ?
C31 H31 0.9500 . ?
C31 C32 1.363(8) . ?
C32 H32 0.9500 . ?
C32 C33 1.380(7) . ?
C33 C34 1.388(7) . ?
C34 H34 0.9500 . ?
C34 C35 1.372(7) . ?
C35 H35 0.9500 . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C36 H36C 0.9900 . ?
C36 H36D 0.9900 . ?
C36 C37 1.439(18) . ?
C36 C39 1.640(19) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C37 C38 1.457(15) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C38 C41 1.85(2) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C39 C40 1.500(14) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C40 C41 1.522(12) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C41 H41D 0.9800 . ?
C41 H41E 0.9800 . ?
C41 H41F 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
C27 O1 B010 122.1(4) . . ?
C29 O2 B010 123.1(5) . . ?
C33 O3 C36 119.2(5) . . ?
C2 C1 C6 117.6(6) . . ?
C2 C1 C7 126.8(5) . . ?
C6 C1 C7 115.5(5) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 C1 122.3(6) . . ?
C3 C2 H2 118.8 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(6) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.9(7) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.7(6) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 121.7(6) . . ?
C1 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C8 C7 C1 115.9(5) . . ?
C14 C7 C1 123.2(6) . . ?
C14 C7 C8 121.0(6) . . ?
C9 C8 C7 117.9(5) . . ?
C13 C8 C7 124.2(5) . . ?
C13 C8 C9 117.8(5) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.4(6) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.8(6) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0(6) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.7(6) . . ?
C13 C12 H12 120.1 . . ?
C8 C13 H13 119.4 . . ?
C12 C13 C8 121.2(6) . . ?
C12 C13 H13 119.4 . . ?
C7 C14 C15 121.2(6) . . ?
C7 C14 C21 122.8(7) . . ?
C15 C14 C21 116.0(5) . . ?
C16 C15 C14 124.0(5) . . ?
C16 C15 C20 120.0(6) . . ?
C20 C15 C14 115.9(6) . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.3(6) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.1(7) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 121.1(7) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.5(7) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 C19 118.0(6) . . ?
C15 C20 H20 121.0 . . ?
C19 C20 H20 121.0 . . ?
C22 C21 C14 116.8(6) . . ?
C22 C21 C26 119.4(5) . . ?
C26 C21 C14 123.2(5) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.8(6) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.7(5) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C25 118.7(5) . . ?
C23 C24 C27 120.4(5) . . ?
C25 C24 C27 120.9(5) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 C24 119.9(5) . . ?
C26 C25 H25 120.1 . . ?
C21 C26 C25 120.5(5) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
O1 C27 C24 114.7(5) . . ?
O1 C27 C28 121.3(5) . . ?
C28 C27 C24 124.0(5) . . ?
C27 C28 H28 119.8 . . ?
C27 C28 C29 120.4(5) . . ?
C29 C28 H28 119.8 . . ?
O2 C29 C28 120.1(5) . . ?
O2 C29 C30 116.2(5) . . ?
C28 C29 C30 123.6(5) . . ?
C31 C30 C29 120.5(5) . . ?
C35 C30 C29 122.6(5) . . ?
C35 C30 C31 116.9(5) . . ?
C30 C31 H31 119.3 . . ?
C32 C31 C30 121.4(5) . . ?
C32 C31 H31 119.3 . . ?
C31 C32 H32 119.6 . . ?
C31 C32 C33 120.8(5) . . ?
C33 C32 H32 119.6 . . ?
O3 C33 C32 116.1(5) . . ?
O3 C33 C34 124.8(5) . . ?
C32 C33 C34 119.1(5) . . ?
C33 C34 H34 120.3 . . ?
C35 C34 C33 119.5(5) . . ?
C35 C34 H34 120.3 . . ?
C30 C35 H35 118.9 . . ?
C34 C35 C30 122.3(5) . . ?
C34 C35 H35 118.9 . . ?
O3 C36 H36A 111.5 . . ?
O3 C36 H36B 111.5 . . ?
O3 C36 H36C 108.1 . . ?
O3 C36 H36D 108.1 . . ?
O3 C36 C37 116.8(9) . . ?
O3 C36 C39 101.6(7) . . ?
H36A C36 H36B 109.3 . . ?
H36C C36 H36D 107.3 . . ?
C37 C36 H36C 108.1 . . ?
C37 C36 H36D 108.1 . . ?
C39 C36 H36A 111.5 . . ?
C39 C36 H36B 111.5 . . ?
C36 C37 H37A 111.0 . . ?
C36 C37 H37B 111.0 . . ?
C36 C37 C38 103.9(15) . . ?
H37A C37 H37B 109.0 . . ?
C38 C37 H37A 111.0 . . ?
C38 C37 H37B 111.0 . . ?
C37 C38 H38A 111.1 . . ?
C37 C38 H38B 111.1 . . ?
C37 C38 C41 103.2(14) . . ?
H38A C38 H38B 109.1 . . ?
C41 C38 H38A 111.1 . . ?
C41 C38 H38B 111.1 . . ?
C36 C39 H39A 109.8 . . ?
C36 C39 H39B 109.8 . . ?
H39A C39 H39B 108.2 . . ?
C40 C39 C36 109.6(12) . . ?
C40 C39 H39A 109.8 . . ?
C40 C39 H39B 109.8 . . ?
C39 C40 H40A 111.1 . . ?
C39 C40 H40B 111.1 . . ?
C39 C40 C41 103.5(11) . . ?
H40A C40 H40B 109.0 . . ?
C41 C40 H40A 111.1 . . ?
C41 C40 H40B 111.1 . . ?
C38 C41 H41D 109.5 . . ?
C38 C41 H41E 109.5 . . ?
C38 C41 H41F 109.5 . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
H41D C41 H41E 109.5 . . ?
H41D C41 H41F 109.5 . . ?
H41E C41 H41F 109.5 . . ?
F1 B010 F2 111.1(5) . . ?
F1 B010 O1 108.5(5) . . ?
F1 B010 O2 109.2(6) . . ?
F2 B010 O1 108.4(5) . . ?
F2 B010 O2 108.6(5) . . ?
O2 B010 O1 111.1(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cc
_database_code_depnum_ccdc_archive 'CCDC 1832405'
_audit_update_record             
;
2018-05-10 deposited with the CCDC.
2018-05-28 downloaded from the CCDC.
;
_audit_creation_date             2018-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C37 H29 B F2 O3'
_chemical_formula_sum            'C37 H29 B F2 O3'
_chemical_formula_weight         570.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.321(6)
_cell_length_b                   10.078(6)
_cell_length_c                   18.829(12)
_cell_angle_alpha                80.622(12)
_cell_angle_beta                 79.030(13)
_cell_angle_gamma                85.715(12)
_cell_volume                     1711.3(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    533
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      17.7251
_cell_measurement_theta_min      2.1799
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.2007
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            5994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.005
_diffrn_reflns_theta_max         25.005
_diffrn_reflns_theta_min         2.180
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2021
_reflns_number_total             5994
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.848
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         5994
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.2308
_refine_ls_R_factor_gt           0.1119
_refine_ls_restrained_S_all      0.930
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0731P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2480
_refine_ls_wR_factor_ref         0.2986
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 O3, O3, C33, C36, C36, C37
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C36(H36A,H36B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23),
  C25(H25), C26(H26), C28(H28), C31(H31), C32(H32), C34(H34), C35(H35)
3.c Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.8264(4) -0.3138(3) 0.1587(2) 0.1021(13) Uani 1 1 d . . . . .
F2 F 1.0296(4) -0.2833(4) 0.0713(2) 0.1033(13) Uani 1 1 d . . . . .
O1 O 0.9308(4) -0.1064(4) 0.1331(2) 0.0844(14) Uani 1 1 d . . . . .
O2 O 0.8085(4) -0.1886(4) 0.0459(2) 0.0808(13) Uani 1 1 d . . . . .
O3 O 0.4590(5) -0.0187(6) -0.2102(3) 0.131(2) Uani 1 1 d . U . . .
C1 C 0.8179(7) 0.3249(6) 0.3600(3) 0.0821(18) Uani 1 1 d . . . . .
H1 H 0.8815 0.2505 0.3533 0.099 Uiso 1 1 calc R . . . .
C2 C 0.6743(9) 0.3041(9) 0.3949(4) 0.104(2) Uani 1 1 d . . . . .
H2 H 0.6419 0.2173 0.4105 0.125 Uiso 1 1 calc R . . . .
C3 C 0.5791(9) 0.4157(11) 0.4062(4) 0.117(3) Uani 1 1 d . . . . .
H3 H 0.4827 0.4043 0.4297 0.141 Uiso 1 1 calc R . . . .
C4 C 0.6291(8) 0.5396(10) 0.3827(5) 0.127(3) Uani 1 1 d . . . . .
H4 H 0.5651 0.6137 0.3894 0.152 Uiso 1 1 calc R . . . .
C5 C 0.7728(7) 0.5608(7) 0.3487(4) 0.097(2) Uani 1 1 d . . . . .
H5 H 0.8051 0.6479 0.3349 0.117 Uiso 1 1 calc R . . . .
C6 C 0.8689(6) 0.4506(6) 0.3353(3) 0.0689(16) Uani 1 1 d . . . . .
C7 C 1.0252(6) 0.4769(6) 0.2990(3) 0.0678(16) Uani 1 1 d . . . . .
C8 C 1.0948(6) 0.5816(6) 0.3305(3) 0.0664(16) Uani 1 1 d . . . . .
C9 C 1.1356(7) 0.7033(6) 0.2906(4) 0.0834(19) Uani 1 1 d . . . . .
H9 H 1.1185 0.7264 0.2429 0.100 Uiso 1 1 calc R . . . .
C10 C 1.2024(8) 0.7914(7) 0.3216(5) 0.100(2) Uani 1 1 d . . . . .
H10 H 1.2298 0.8743 0.2947 0.120 Uiso 1 1 calc R . . . .
C11 C 1.2279(8) 0.7592(8) 0.3892(5) 0.106(3) Uani 1 1 d . . . . .
H11 H 1.2757 0.8187 0.4086 0.127 Uiso 1 1 calc R . . . .
C12 C 1.1838(7) 0.6363(8) 0.4323(4) 0.100(2) Uani 1 1 d . . . . .
H12 H 1.2001 0.6139 0.4800 0.120 Uiso 1 1 calc R . . . .
C13 C 1.1150(7) 0.5501(7) 0.4005(4) 0.087(2) Uani 1 1 d . . . . .
H13 H 1.0822 0.4692 0.4279 0.104 Uiso 1 1 calc R . . . .
C14 C 1.0954(6) 0.4239(5) 0.2440(3) 0.0649(16) Uani 1 1 d . . . . .
C15 C 1.2506(6) 0.4570(5) 0.2066(3) 0.0630(15) Uani 1 1 d . . . . .
C16 C 1.3686(6) 0.4401(6) 0.2439(4) 0.0806(18) Uani 1 1 d . . . . .
H16 H 1.3549 0.4062 0.2936 0.097 Uiso 1 1 calc R . . . .
C17 C 1.5060(7) 0.4744(7) 0.2057(5) 0.097(2) Uani 1 1 d . . . . .
H17 H 1.5839 0.4640 0.2309 0.116 Uiso 1 1 calc R . . . .
C18 C 1.5308(8) 0.5208(7) 0.1359(5) 0.098(2) Uani 1 1 d . . . . .
H18 H 1.6251 0.5419 0.1121 0.118 Uiso 1 1 calc R . . . .
C19 C 1.4137(7) 0.5391(6) 0.0961(4) 0.0809(18) Uani 1 1 d . . . . .
H19 H 1.4290 0.5751 0.0467 0.097 Uiso 1 1 calc R . . . .
C20 C 1.2792(6) 0.5024(5) 0.1322(4) 0.0710(17) Uani 1 1 d . . . . .
H20 H 1.2033 0.5078 0.1060 0.085 Uiso 1 1 calc R . . . .
C21 C 1.0333(6) 0.3179(5) 0.2100(3) 0.0598(15) Uani 1 1 d . . . . .
C22 C 0.9324(6) 0.3515(5) 0.1620(3) 0.0714(17) Uani 1 1 d . . . . .
H22 H 0.8964 0.4399 0.1524 0.086 Uiso 1 1 calc R . . . .
C23 C 0.8877(6) 0.2531(6) 0.1297(3) 0.0697(16) Uani 1 1 d . . . . .
H23 H 0.8210 0.2766 0.0982 0.084 Uiso 1 1 calc R . . . .
C24 C 0.9376(5) 0.1214(5) 0.1420(3) 0.0579(14) Uani 1 1 d . . . . .
C25 C 1.0381(6) 0.0882(5) 0.1917(3) 0.0661(16) Uani 1 1 d . . . . .
H25 H 1.0711 -0.0009 0.2027 0.079 Uiso 1 1 calc R . . . .
C26 C 1.0856(6) 0.1834(5) 0.2227(3) 0.0693(16) Uani 1 1 d . . . . .
H26 H 1.1542 0.1600 0.2531 0.083 Uiso 1 1 calc R . . . .
C27 C 0.8925(5) 0.0145(5) 0.1068(3) 0.0569(14) Uani 1 1 d . . . . .
C28 C 0.8158(6) 0.0393(5) 0.0512(3) 0.0637(15) Uani 1 1 d . . . . .
H28 H 0.7906 0.1276 0.0330 0.076 Uiso 1 1 calc R . . . .
C29 C 0.7748(5) -0.0660(5) 0.0211(3) 0.0582(14) Uani 1 1 d . . . . .
C30 C 0.6907(6) -0.0474(5) -0.0384(3) 0.0594(14) Uani 1 1 d . . . . .
C31 C 0.6560(6) 0.0790(6) -0.0768(3) 0.0668(16) Uani 1 1 d . . . . .
H31 H 0.6863 0.1557 -0.0633 0.080 Uiso 1 1 calc R . . . .
C32 C 0.5816(6) 0.0934(6) -0.1316(3) 0.0698(16) Uani 1 1 d . . . . .
H32 H 0.5598 0.1789 -0.1551 0.084 Uiso 1 1 calc R . . . .
C33 C 0.5361(6) -0.0208(7) -0.1539(4) 0.0773(16) Uani 1 1 d . U . . .
C34 C 0.5707(6) -0.1490(6) -0.1184(4) 0.0761(18) Uani 1 1 d . . . . .
H34 H 0.5430 -0.2252 -0.1334 0.091 Uiso 1 1 calc R . . . .
C35 C 0.6452(6) -0.1619(6) -0.0616(3) 0.0722(17) Uani 1 1 d . . . . .
H35 H 0.6664 -0.2473 -0.0377 0.087 Uiso 1 1 calc R . . . .
C36 C 0.4201(10) 0.0886(8) -0.2495(5) 0.137(3) Uani 1 1 d . U . . .
H36A H 0.5045 0.1388 -0.2748 0.164 Uiso 1 1 calc R . . . .
H36B H 0.3546 0.1457 -0.2197 0.164 Uiso 1 1 calc R . . . .
C37 C 0.3411(9) 0.0386(10) -0.3046(4) 0.147(3) Uani 1 1 d . U . . .
H37A H 0.4021 0.0497 -0.3522 0.221 Uiso 1 1 calc GR . . . .
H37B H 0.2506 0.0900 -0.3068 0.221 Uiso 1 1 calc GR . . . .
H37C H 0.3214 -0.0548 -0.2891 0.221 Uiso 1 1 calc GR . . . .
B1 B 0.8992(9) -0.2271(8) 0.1030(5) 0.078(2) 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
F1 B1 1.358(8) . ?
F2 B1 1.374(9) . ?
O1 C27 1.289(6) . ?
O1 B1 1.492(8) . ?
O2 C29 1.285(6) . ?
O2 B1 1.478(7) . ?
O3 C33 1.386(7) . ?
O3 C36 1.277(8) . ?
C1 H1 0.9300 . ?
C1 C2 1.389(9) . ?
C1 C6 1.364(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.398(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.341(10) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(8) . ?
C6 C7 1.510(8) . ?
C7 C8 1.529(7) . ?
C7 C14 1.287(8) . ?
C8 C9 1.369(7) . ?
C8 C13 1.349(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.323(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.408(9) . ?
C12 H12 0.9300 . ?
C12 C13 1.386(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.519(7) . ?
C14 C21 1.530(7) . ?
C15 C16 1.400(7) . ?
C15 C20 1.382(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.305(9) . ?
C18 H18 0.9300 . ?
C18 C19 1.423(9) . ?
C19 H19 0.9300 . ?
C19 C20 1.354(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.412(7) . ?
C21 C26 1.404(7) . ?
C22 H22 0.9300 . ?
C22 C23 1.372(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.372(7) . ?
C24 C25 1.431(7) . ?
C24 C27 1.477(7) . ?
C25 H25 0.9300 . ?
C25 C26 1.343(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.358(7) . ?
C28 H28 0.9300 . ?
C28 C29 1.390(7) . ?
C29 C30 1.466(7) . ?
C30 C31 1.406(7) . ?
C30 C35 1.417(7) . ?
C31 H31 0.9300 . ?
C31 C32 1.333(7) . ?
C32 H32 0.9300 . ?
C32 C33 1.407(8) . ?
C33 C34 1.399(8) . ?
C34 H34 0.9300 . ?
C34 C35 1.367(7) . ?
C35 H35 0.9300 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 C37 1.546(9) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 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
C27 O1 B1 122.7(5) . . ?
C29 O2 B1 123.7(5) . . ?
C36 O3 C33 124.2(7) . . ?
C2 C1 H1 118.9 . . ?
C6 C1 H1 118.9 . . ?
C6 C1 C2 122.2(7) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.0(7) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.0(8) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 118.9 . . ?
C3 C4 C5 122.2(8) . . ?
C5 C4 H4 118.9 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.7(7) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 117.8(6) . . ?
C1 C6 C7 123.7(6) . . ?
C5 C6 C7 118.5(5) . . ?
C6 C7 C8 113.9(5) . . ?
C14 C7 C6 125.0(5) . . ?
C14 C7 C8 121.0(5) . . ?
C9 C8 C7 122.4(5) . . ?
C13 C8 C7 117.3(5) . . ?
C13 C8 C9 120.3(5) . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.4(6) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.8(7) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.1(6) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 121.4 . . ?
C13 C12 C11 117.3(7) . . ?
C13 C12 H12 121.4 . . ?
C8 C13 C12 121.1(6) . . ?
C8 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C7 C14 C15 123.8(5) . . ?
C7 C14 C21 123.8(5) . . ?
C15 C14 C21 112.4(5) . . ?
C16 C15 C14 122.8(6) . . ?
C20 C15 C14 119.4(5) . . ?
C20 C15 C16 117.7(5) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.0(6) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 118.7 . . ?
C18 C17 C16 122.6(7) . . ?
C18 C17 H17 118.7 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.0(7) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 121.0 . . ?
C20 C19 C18 118.0(6) . . ?
C20 C19 H19 121.0 . . ?
C15 C20 H20 118.8 . . ?
C19 C20 C15 122.4(6) . . ?
C19 C20 H20 118.8 . . ?
C22 C21 C14 122.4(5) . . ?
C26 C21 C14 119.1(5) . . ?
C26 C21 C22 118.3(5) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 C21 119.7(5) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 118.8 . . ?
C22 C23 C24 122.4(5) . . ?
C24 C23 H23 118.8 . . ?
C23 C24 C25 117.4(5) . . ?
C23 C24 C27 123.2(5) . . ?
C25 C24 C27 119.5(5) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 C24 121.1(5) . . ?
C26 C25 H25 119.4 . . ?
C21 C26 H26 119.5 . . ?
C25 C26 C21 121.1(5) . . ?
C25 C26 H26 119.5 . . ?
O1 C27 C24 115.0(5) . . ?
O1 C27 C28 121.5(5) . . ?
C28 C27 C24 123.5(5) . . ?
C27 C28 H28 119.7 . . ?
C27 C28 C29 120.7(5) . . ?
C29 C28 H28 119.7 . . ?
O2 C29 C28 120.3(5) . . ?
O2 C29 C30 115.8(5) . . ?
C28 C29 C30 123.9(5) . . ?
C31 C30 C29 123.7(5) . . ?
C31 C30 C35 116.9(5) . . ?
C35 C30 C29 119.4(5) . . ?
C30 C31 H31 118.7 . . ?
C32 C31 C30 122.7(5) . . ?
C32 C31 H31 118.7 . . ?
C31 C32 H32 120.0 . . ?
C31 C32 C33 120.0(6) . . ?
C33 C32 H32 120.0 . . ?
O3 C33 C32 125.3(6) . . ?
O3 C33 C34 115.3(6) . . ?
C34 C33 C32 119.4(6) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 C33 119.9(6) . . ?
C35 C34 H34 120.1 . . ?
C30 C35 H35 119.4 . . ?
C34 C35 C30 121.2(6) . . ?
C34 C35 H35 119.4 . . ?
O3 C36 H36A 110.8 . . ?
O3 C36 H36B 110.8 . . ?
O3 C36 C37 104.6(7) . . ?
H36A C36 H36B 108.9 . . ?
C37 C36 H36A 110.8 . . ?
C37 C36 H36B 110.8 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
F1 B1 F2 112.0(6) . . ?
F1 B1 O1 108.3(6) . . ?
F1 B1 O2 109.5(5) . . ?
F2 B1 O1 108.3(5) . . ?
F2 B1 O2 107.9(6) . . ?
O2 B1 O1 110.8(5) . . ?

_platon_squeeze_details          
;

;

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_qq_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1558346'
_audit_update_record             
;
2018-05-10 deposited with the CCDC.
2018-05-28 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            'C47 H50 B F2 O3'
_chemical_formula_weight         711.68

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2196(17)
_cell_length_b                   9.9971(18)
_cell_length_c                   21.908(4)
_cell_angle_alpha                91.519(2)
_cell_angle_beta                 90.590(2)
_cell_angle_gamma                95.333(2)
_cell_volume                     2009.6(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_F_000             758
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14145
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_av_R_equivalents  0.0293
_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       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.395
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_full        25.010
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7034
_reflns_number_gt                4242
_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)+(0.0626P)²+0.2907P] 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         7034
_refine_ls_number_parameters     478
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1417
_refine_ls_wR_factor_gt          0.1197
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.012
_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 0.51712(15) 0.74143(14) 0.02962(7) 0.0706(4) Uani 1 1 d . . . . .
F2 F 0.70402(16) 0.71661(13) 0.09423(6) 0.0664(4) Uani 1 1 d . . . . .
O1 O 0.61784(17) 0.92535(14) 0.08718(7) 0.0544(4) Uani 1 1 d . . . . .
O2 O 0.75116(17) 0.82581(14) 0.00415(7) 0.0540(4) Uani 1 1 d . . . . .
O3 O 1.14328(18) 0.98688(15) -0.22122(7) 0.0583(5) Uani 1 1 d . . . . .
C1 C 0.2724(3) 1.5244(2) 0.09321(11) 0.0528(6) Uani 1 1 d . . . . .
H1 H 0.3568 1.5212 0.0705 0.063 Uiso 1 1 calc R U . . .
C2 C 0.1419(3) 1.5438(2) 0.06415(12) 0.0620(7) Uani 1 1 d . . . . .
H2 H 0.1392 1.5546 0.0221 0.074 Uiso 1 1 calc R U . . .
C3 C 0.0170(3) 1.5473(2) 0.09718(14) 0.0602(7) Uani 1 1 d . . . . .
H3 H -0.0699 1.5622 0.0777 0.072 Uiso 1 1 calc R U . . .
C4 C 0.0197(3) 1.5290(2) 0.15813(13) 0.0587(7) Uani 1 1 d . . . . .
H4 H -0.0660 1.5287 0.1802 0.070 Uiso 1 1 calc R U . . .
C5 C 0.1483(2) 1.5109(2) 0.18771(11) 0.0501(6) Uani 1 1 d . . . . .
H5 H 0.1488 1.4993 0.2297 0.060 Uiso 1 1 calc R U . . .
C6 C 0.2773(2) 1.5095(2) 0.15573(10) 0.0412(5) Uani 1 1 d . . . . .
C7 C 0.4218(2) 1.4937(2) 0.18564(10) 0.0450(6) Uani 1 1 d . . . . .
C8 C 0.4792(2) 1.5795(2) 0.22847(10) 0.0468(6) Uani 1 1 d . . . . .
C9 C 0.4008(2) 1.6952(2) 0.25187(11) 0.0467(6) Uani 1 1 d . . . . .
C10 C 0.3579(3) 1.7935(2) 0.21434(12) 0.0577(7) Uani 1 1 d . . . . .
H10 H 0.3798 1.7900 0.1730 0.069 Uiso 1 1 calc R U . . .
C11 C 0.2835(3) 1.8964(3) 0.23691(16) 0.0720(8) Uani 1 1 d . . . . .
H11 H 0.2558 1.9619 0.2110 0.086 Uiso 1 1 calc R U . . .
C12 C 0.2507(3) 1.9025(3) 0.29675(18) 0.0831(9) Uani 1 1 d . . . . .
H12 H 0.1971 1.9705 0.3115 0.100 Uiso 1 1 calc R U . . .
C13 C 0.2954(4) 1.8100(4) 0.33594(15) 0.0927(10) Uani 1 1 d . . . . .
H13 H 0.2750 1.8166 0.3773 0.111 Uiso 1 1 calc R U . . .
C14 C 0.3720(3) 1.7057(3) 0.31331(12) 0.0711(8) Uani 1 1 d . . . . .
H14 H 0.4037 1.6430 0.3398 0.085 Uiso 1 1 calc R U . . .
C15 C 0.6253(2) 1.5689(2) 0.25847(10) 0.0459(6) Uani 1 1 d . . . . .
C16 C 0.7274(3) 1.6802(2) 0.25799(11) 0.0546(6) Uani 1 1 d . . . . .
H16 H 0.7059 1.7563 0.2375 0.066 Uiso 1 1 calc R U . . .
C17 C 0.8600(3) 1.6793(3) 0.28755(13) 0.0686(8) Uani 1 1 d . . . . .
H17 H 0.9275 1.7544 0.2866 0.082 Uiso 1 1 calc R U . . .
C18 C 0.8923(3) 1.5688(3) 0.31813(13) 0.0779(9) Uani 1 1 d . . . . .
H18 H 0.9814 1.5685 0.3384 0.094 Uiso 1 1 calc R U . . .
C19 C 0.7926(4) 1.4572(3) 0.31890(13) 0.0792(9) Uani 1 1 d . . . . .
H19 H 0.8146 1.3815 0.3396 0.095 Uiso 1 1 calc R U . . .
C20 C 0.6601(3) 1.4576(3) 0.28906(12) 0.0642(7) Uani 1 1 d . . . . .
H20 H 0.5937 1.3817 0.2896 0.077 Uiso 1 1 calc R U . . .
C21 C 0.4964(2) 1.3769(2) 0.16029(10) 0.0412(5) Uani 1 1 d . . . . .
C22 C 0.6203(2) 1.3950(2) 0.12510(10) 0.0455(6) Uani 1 1 d . . . . .
H22 H 0.6680 1.4806 0.1217 0.055 Uiso 1 1 calc R U . . .
C23 C 0.6738(2) 1.2872(2) 0.09492(10) 0.0444(6) Uani 1 1 d . . . . .
H23 H 0.7562 1.3014 0.0710 0.053 Uiso 1 1 calc R U . . .
C24 C 0.6063(2) 1.15834(19) 0.09978(9) 0.0373(5) Uani 1 1 d . . . . .
C25 C 0.4864(2) 1.1396(2) 0.13715(10) 0.0462(6) Uani 1 1 d . . . . .
H25 H 0.4427 1.0533 0.1428 0.055 Uiso 1 1 calc R U . . .
C26 C 0.4312(2) 1.2477(2) 0.16608(11) 0.0504(6) Uani 1 1 d . . . . .
H26 H 0.3485 1.2335 0.1899 0.060 Uiso 1 1 calc R U . . .
C27 C 0.6557(2) 1.0430(2) 0.06535(10) 0.0384(5) Uani 1 1 d . . . . .
C28 C 0.7351(2) 1.0559(2) 0.01307(10) 0.0461(6) Uani 1 1 d . . . . .
H28 H 0.7554 1.1406 -0.0031 0.055 Uiso 1 1 calc R U . . .
C29 C 0.7857(2) 0.9453(2) -0.01621(10) 0.0381(5) Uani 1 1 d . . . . .
C30 C 0.8788(2) 0.9541(2) -0.06957(9) 0.0379(5) Uani 1 1 d . . . . .
C31 C 0.9172(2) 0.8385(2) -0.09945(10) 0.0457(6) Uani 1 1 d . . . . .
H31 H 0.8828 0.7550 -0.0850 0.055 Uiso 1 1 calc R U . . .
C32 C 1.0053(2) 0.8449(2) -0.15006(10) 0.0483(6) Uani 1 1 d . . . . .
H32 H 1.0295 0.7663 -0.1695 0.058 Uiso 1 1 calc R U . . .
C33 C 1.0572(2) 0.9684(2) -0.17176(10) 0.0437(5) Uani 1 1 d . . . . .
C34 C 1.0209(3) 1.0848(2) -0.14215(11) 0.0527(6) Uani 1 1 d . . . . .
H34 H 1.0563 1.1682 -0.1564 0.063 Uiso 1 1 calc R U . . .
C35 C 0.9335(3) 1.0777(2) -0.09209(10) 0.0491(6) Uani 1 1 d . . . . .
H35 H 0.9101 1.1567 -0.0727 0.059 Uiso 1 1 calc R U . . .
C36 C 1.1991(3) 0.8723(2) -0.25025(11) 0.0550(6) Uani 1 1 d . . . . .
H36A H 1.1198 0.8094 -0.2655 0.066 Uiso 1 1 calc R U . . .
H36B H 1.2568 0.8268 -0.2215 0.066 Uiso 1 1 calc R U . . .
C37 C 1.2920(3) 0.9241(3) -0.30212(11) 0.0596(7) Uani 1 1 d . . . . .
H37A H 1.3502 0.8538 -0.3163 0.071 Uiso 1 1 calc R U . . .
H37B H 1.3582 0.9991 -0.2871 0.071 Uiso 1 1 calc R U . . .
C38 C 1.2057(3) 0.9696(3) -0.35555(11) 0.0638(7) Uani 1 1 d . . . . .
H38A H 1.1447 0.8929 -0.3724 0.077 Uiso 1 1 calc R U . . .
H38B H 1.1420 1.0350 -0.3408 0.077 Uiso 1 1 calc R U . . .
C39 C 1.2982(3) 1.0308(3) -0.40572(12) 0.0776(8) Uani 1 1 d . . . . .
H39A H 1.3653 0.9671 -0.4190 0.093 Uiso 1 1 calc R U . . .
H39B H 1.3556 1.1101 -0.3893 0.093 Uiso 1 1 calc R U . . .
C40 C 1.2118(3) 1.0702(3) -0.46080(13) 0.0821(9) Uani 1 1 d . . . . .
H40A H 1.1556 0.9906 -0.4776 0.099 Uiso 1 1 calc R U . . .
H40B H 1.1436 1.1327 -0.4473 0.099 Uiso 1 1 calc R U . . .
C41 C 1.3031(4) 1.1333(4) -0.51043(14) 0.0958(10) Uani 1 1 d . . . . .
H41A H 1.3717 1.0708 -0.5236 0.115 Uiso 1 1 calc R U . . .
H41B H 1.3592 1.2129 -0.4935 0.115 Uiso 1 1 calc R U . . .
C42 C 1.2198(3) 1.1727(3) -0.56550(13) 0.0825(9) Uani 1 1 d . . . . .
H42A H 1.1686 1.0922 -0.5839 0.099 Uiso 1 1 calc R U . . .
H42B H 1.1470 1.2306 -0.5519 0.099 Uiso 1 1 calc R U . . .
C43 C 1.3097(4) 1.2437(4) -0.61383(15) 0.0994(11) Uani 1 1 d . . . . .
H43A H 1.3779 1.1836 -0.6297 0.119 Uiso 1 1 calc R U . . .
H43B H 1.3660 1.3211 -0.5951 0.119 Uiso 1 1 calc R U . . .
C44 C 1.2225(4) 1.2902(4) -0.66629(15) 0.1105(12) Uani 1 1 d . . . . .
H44A H 1.2872 1.3344 -0.6951 0.166 Uiso 1 1 calc R U . . .
H44B H 1.1683 1.2142 -0.6860 0.166 Uiso 1 1 calc R U . . .
H44C H 1.1565 1.3519 -0.6513 0.166 Uiso 1 1 calc R U . . .
B1 B 0.6457(3) 0.7988(2) 0.05415(13) 0.0492(7) Uani 1 1 d . . . . .
C45 C 1.6798(7) 1.3580(8) -0.5056(3) 0.246(4) Uani 1 1 d . . . . .
H45A H 1.6356 1.2785 -0.4872 0.370 Uiso 1 1 calc R U . . .
H45B H 1.6331 1.4346 -0.4913 0.370 Uiso 1 1 calc R U . . .
H45C H 1.6689 1.3489 -0.5492 0.370 Uiso 1 1 calc R U . . .
C46 C 1.8321(9) 1.3759(8) -0.4896(4) 0.261(4) Uani 1 1 d D . . . .
H46A H 1.8371 1.3787 -0.4453 0.314 Uiso 1 1 calc R U . . .
H46B H 1.8725 1.2939 -0.5027 0.314 Uiso 1 1 calc R U . . .
C47 C 1.9262(6) 1.4779(6) -0.5079(3) 0.175(2) Uani 1 1 d D . . . .
H47A H 1.8747 1.5570 -0.5007 0.210 Uiso 1 1 calc R U . . .
H47B H 1.9276 1.4652 -0.5520 0.210 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 B1 1.366(3) . ?
F2 B1 1.359(3) . ?
O1 C27 1.300(2) . ?
O1 B1 1.485(3) . ?
O2 C29 1.299(2) . ?
O2 B1 1.486(3) . ?
O3 C33 1.356(3) . ?
O3 C36 1.435(3) . ?
C1 C6 1.382(3) . ?
C1 C2 1.387(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.353(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.501(3) . ?
C7 C8 1.327(3) . ?
C7 C21 1.506(3) . ?
C8 C9 1.501(3) . ?
C8 C15 1.506(3) . ?
C9 C14 1.378(3) . ?
C9 C10 1.381(3) . ?
C10 C11 1.372(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.350(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.367(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.397(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.376(3) . ?
C15 C16 1.389(3) . ?
C16 C17 1.379(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.362(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.379(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.379(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.383(3) . ?
C21 C22 1.385(3) . ?
C22 C23 1.382(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.385(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.384(3) . ?
C24 C27 1.471(3) . ?
C25 C26 1.379(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C28 1.368(3) . ?
C28 C29 1.384(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.457(3) . ?
C30 C31 1.389(3) . ?
C30 C35 1.395(3) . ?
C31 C32 1.380(3) . ?
C31 H31 0.9300 . ?
C32 C33 1.380(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.387(3) . ?
C34 C35 1.367(3) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 C37 1.504(3) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C38 1.512(3) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.506(4) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C40 1.520(4) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 C41 1.498(4) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 C42 1.504(4) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 C43 1.503(4) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 C44 1.504(4) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C45 C46 1.438(8) . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C46 C47 1.349(6) . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C47 C47 1.428(10) 2_984 ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?

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
C27 O1 B1 122.20(18) . . ?
C29 O2 B1 122.99(17) . . ?
C33 O3 C36 118.99(17) . . ?
C6 C1 C2 120.2(2) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.2(2) . . ?
C1 C6 C7 118.5(2) . . ?
C5 C6 C7 123.3(2) . . ?
C8 C7 C6 122.1(2) . . ?
C8 C7 C21 124.0(2) . . ?
C6 C7 C21 113.81(18) . . ?
C7 C8 C9 122.0(2) . . ?
C7 C8 C15 123.7(2) . . ?
C9 C8 C15 114.34(18) . . ?
C14 C9 C10 118.3(2) . . ?
C14 C9 C8 119.1(2) . . ?
C10 C9 C8 122.6(2) . . ?
C11 C10 C9 121.2(3) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.8(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C14 119.5(3) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C9 C14 C13 120.2(3) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C20 C15 C16 118.3(2) . . ?
C20 C15 C8 123.5(2) . . ?
C16 C15 C8 118.1(2) . . ?
C17 C16 C15 120.9(2) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 120.1(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.8(3) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 120.2(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 120.7(3) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C26 C21 C22 118.19(19) . . ?
C26 C21 C7 119.38(19) . . ?
C22 C21 C7 122.02(19) . . ?
C23 C22 C21 120.7(2) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 120.9(2) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C25 C24 C23 118.29(19) . . ?
C25 C24 C27 119.63(18) . . ?
C23 C24 C27 122.06(19) . . ?
C26 C25 C24 120.6(2) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C21 121.2(2) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
O1 C27 C28 120.98(19) . . ?
O1 C27 C24 115.87(18) . . ?
C28 C27 C24 123.14(19) . . ?
C27 C28 C29 121.3(2) . . ?
C27 C28 H28 119.4 . . ?
C29 C28 H28 119.4 . . ?
O2 C29 C28 119.79(19) . . ?
O2 C29 C30 116.60(18) . . ?
C28 C29 C30 123.61(19) . . ?
C31 C30 C35 117.7(2) . . ?
C31 C30 C29 120.66(19) . . ?
C35 C30 C29 121.60(18) . . ?
C32 C31 C30 121.5(2) . . ?
C32 C31 H31 119.3 . . ?
C30 C31 H31 119.3 . . ?
C31 C32 C33 119.7(2) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
O3 C33 C32 124.9(2) . . ?
O3 C33 C34 115.6(2) . . ?
C32 C33 C34 119.5(2) . . ?
C35 C34 C33 120.5(2) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C34 C35 C30 121.1(2) . . ?
C34 C35 H35 119.5 . . ?
C30 C35 H35 119.5 . . ?
O3 C36 C37 106.77(19) . . ?
O3 C36 H36A 110.4 . . ?
C37 C36 H36A 110.4 . . ?
O3 C36 H36B 110.4 . . ?
C37 C36 H36B 110.4 . . ?
H36A C36 H36B 108.6 . . ?
C36 C37 C38 113.8(2) . . ?
C36 C37 H37A 108.8 . . ?
C38 C37 H37A 108.8 . . ?
C36 C37 H37B 108.8 . . ?
C38 C37 H37B 108.8 . . ?
H37A C37 H37B 107.7 . . ?
C39 C38 C37 114.1(2) . . ?
C39 C38 H38A 108.7 . . ?
C37 C38 H38A 108.7 . . ?
C39 C38 H38B 108.7 . . ?
C37 C38 H38B 108.7 . . ?
H38A C38 H38B 107.6 . . ?
C38 C39 C40 114.1(2) . . ?
C38 C39 H39A 108.7 . . ?
C40 C39 H39A 108.7 . . ?
C38 C39 H39B 108.7 . . ?
C40 C39 H39B 108.7 . . ?
H39A C39 H39B 107.6 . . ?
C41 C40 C39 114.4(3) . . ?
C41 C40 H40A 108.7 . . ?
C39 C40 H40A 108.7 . . ?
C41 C40 H40B 108.7 . . ?
C39 C40 H40B 108.7 . . ?
H40A C40 H40B 107.6 . . ?
C40 C41 C42 115.2(3) . . ?
C40 C41 H41A 108.5 . . ?
C42 C41 H41A 108.5 . . ?
C40 C41 H41B 108.5 . . ?
C42 C41 H41B 108.5 . . ?
H41A C41 H41B 107.5 . . ?
C43 C42 C41 115.6(3) . . ?
C43 C42 H42A 108.4 . . ?
C41 C42 H42A 108.4 . . ?
C43 C42 H42B 108.4 . . ?
C41 C42 H42B 108.4 . . ?
H42A C42 H42B 107.4 . . ?
C42 C43 C44 114.4(3) . . ?
C42 C43 H43A 108.7 . . ?
C44 C43 H43A 108.7 . . ?
C42 C43 H43B 108.7 . . ?
C44 C43 H43B 108.7 . . ?
H43A C43 H43B 107.6 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
F2 B1 F1 111.7(2) . . ?
F2 B1 O1 108.5(2) . . ?
F1 B1 O1 108.6(2) . . ?
F2 B1 O2 108.3(2) . . ?
F1 B1 O2 108.9(2) . . ?
O1 B1 O2 110.89(18) . . ?
C46 C45 H45A 109.5 . . ?
C46 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C46 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C47 C46 C45 124.8(8) . . ?
C47 C46 H46A 106.1 . . ?
C45 C46 H46A 106.1 . . ?
C47 C46 H46B 106.1 . . ?
C45 C46 H46B 106.1 . . ?
H46A C46 H46B 106.3 . . ?
C46 C47 C47 133.5(9) . 2_984 ?
C46 C47 H47A 103.8 . . ?
C47 C47 H47A 103.8 2_984 . ?
C46 C47 H47B 103.8 . . ?
C47 C47 H47B 103.8 2_984 . ?
H47A C47 H47B 105.4 . . ?

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 -0.6(4) . . . . ?
C1 C2 C3 C4 -1.3(4) . . . . ?
C2 C3 C4 C5 1.9(4) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C2 C1 C6 C5 1.8(3) . . . . ?
C2 C1 C6 C7 -177.8(2) . . . . ?
C4 C5 C6 C1 -1.2(3) . . . . ?
C4 C5 C6 C7 178.4(2) . . . . ?
C1 C6 C7 C8 120.2(2) . . . . ?
C5 C6 C7 C8 -59.5(3) . . . . ?
C1 C6 C7 C21 -57.0(3) . . . . ?
C5 C6 C7 C21 123.4(2) . . . . ?
C6 C7 C8 C9 2.6(3) . . . . ?
C21 C7 C8 C9 179.5(2) . . . . ?
C6 C7 C8 C15 -178.5(2) . . . . ?
C21 C7 C8 C15 -1.7(4) . . . . ?
C7 C8 C9 C14 122.1(3) . . . . ?
C15 C8 C9 C14 -56.9(3) . . . . ?
C7 C8 C9 C10 -59.0(3) . . . . ?
C15 C8 C9 C10 122.1(2) . . . . ?
C14 C9 C10 C11 -2.5(4) . . . . ?
C8 C9 C10 C11 178.5(2) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C11 C12 C13 2.4(4) . . . . ?
C11 C12 C13 C14 -2.0(5) . . . . ?
C10 C9 C14 C13 2.9(4) . . . . ?
C8 C9 C14 C13 -178.1(2) . . . . ?
C12 C13 C14 C9 -0.7(5) . . . . ?
C7 C8 C15 C20 -57.6(3) . . . . ?
C9 C8 C15 C20 121.4(2) . . . . ?
C7 C8 C15 C16 126.0(2) . . . . ?
C9 C8 C15 C16 -55.0(3) . . . . ?
C20 C15 C16 C17 -0.2(3) . . . . ?
C8 C15 C16 C17 176.4(2) . . . . ?
C15 C16 C17 C18 -0.4(4) . . . . ?
C16 C17 C18 C19 0.6(4) . . . . ?
C17 C18 C19 C20 -0.3(4) . . . . ?
C16 C15 C20 C19 0.6(4) . . . . ?
C8 C15 C20 C19 -175.8(2) . . . . ?
C18 C19 C20 C15 -0.4(4) . . . . ?
C8 C7 C21 C26 119.8(3) . . . . ?
C6 C7 C21 C26 -63.1(3) . . . . ?
C8 C7 C21 C22 -67.8(3) . . . . ?
C6 C7 C21 C22 109.3(2) . . . . ?
C26 C21 C22 C23 2.3(3) . . . . ?
C7 C21 C22 C23 -170.2(2) . . . . ?
C21 C22 C23 C24 -0.9(3) . . . . ?
C22 C23 C24 C25 -2.0(3) . . . . ?
C22 C23 C24 C27 176.4(2) . . . . ?
C23 C24 C25 C26 3.5(3) . . . . ?
C27 C24 C25 C26 -174.85(19) . . . . ?
C24 C25 C26 C21 -2.2(3) . . . . ?
C22 C21 C26 C25 -0.7(3) . . . . ?
C7 C21 C26 C25 172.0(2) . . . . ?
B1 O1 C27 C28 -5.9(3) . . . . ?
B1 O1 C27 C24 173.33(19) . . . . ?
C25 C24 C27 O1 -23.0(3) . . . . ?
C23 C24 C27 O1 158.7(2) . . . . ?
C25 C24 C27 C28 156.2(2) . . . . ?
C23 C24 C27 C28 -22.1(3) . . . . ?
O1 C27 C28 C29 -4.2(3) . . . . ?
C24 C27 C28 C29 176.66(19) . . . . ?
B1 O2 C29 C28 6.7(3) . . . . ?
B1 O2 C29 C30 -173.8(2) . . . . ?
C27 C28 C29 O2 3.8(3) . . . . ?
C27 C28 C29 C30 -175.7(2) . . . . ?
O2 C29 C30 C31 5.2(3) . . . . ?
C28 C29 C30 C31 -175.3(2) . . . . ?
O2 C29 C30 C35 -174.2(2) . . . . ?
C28 C29 C30 C35 5.3(3) . . . . ?
C35 C30 C31 C32 -0.6(3) . . . . ?
C29 C30 C31 C32 180.0(2) . . . . ?
C30 C31 C32 C33 0.1(3) . . . . ?
C36 O3 C33 C32 -7.0(3) . . . . ?
C36 O3 C33 C34 173.06(19) . . . . ?
C31 C32 C33 O3 -179.5(2) . . . . ?
C31 C32 C33 C34 0.4(3) . . . . ?
O3 C33 C34 C35 179.4(2) . . . . ?
C32 C33 C34 C35 -0.5(3) . . . . ?
C33 C34 C35 C30 0.0(4) . . . . ?
C31 C30 C35 C34 0.5(3) . . . . ?
C29 C30 C35 C34 179.9(2) . . . . ?
C33 O3 C36 C37 -178.87(19) . . . . ?
O3 C36 C37 C38 -72.5(3) . . . . ?
C36 C37 C38 C39 175.8(2) . . . . ?
C37 C38 C39 C40 177.1(2) . . . . ?
C38 C39 C40 C41 179.1(3) . . . . ?
C39 C40 C41 C42 179.8(3) . . . . ?
C40 C41 C42 C43 176.4(3) . . . . ?
C41 C42 C43 C44 -176.0(3) . . . . ?
C27 O1 B1 F2 133.2(2) . . . . ?
C27 O1 B1 F1 -105.3(2) . . . . ?
C27 O1 B1 O2 14.4(3) . . . . ?
C29 O2 B1 F2 -133.8(2) . . . . ?
C29 O2 B1 F1 104.6(2) . . . . ?
C29 O2 B1 O1 -14.9(3) . . . . ?
C45 C46 C47 C47 171.6(8) . . . 2_984 ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_mo_20180235-4_0m
_database_code_depnum_ccdc_archive 'CCDC 1832237'
_audit_update_record             
;
2018-05-10 deposited with the CCDC.
2018-05-28 downloaded from the CCDC.
;
_audit_creation_date             2018-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C41 H37 B F2 O3'
_chemical_formula_sum            'C41 H37 B F2 O3'
_chemical_formula_weight         626.51
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.163(3)
_cell_length_b                   10.232(3)
_cell_length_c                   17.761(5)
_cell_angle_alpha                79.786(6)
_cell_angle_beta                 81.679(7)
_cell_angle_gamma                88.050(7)
_cell_volume                     1621.4(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1143
_cell_measurement_temperature    173
_cell_measurement_theta_max      21.17
_cell_measurement_theta_min      2.155
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0561 before and 0.0438 after correction. The Ratio of minimum to maximum transmission is 0.9058. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_av_unetI/netI     0.1314
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12877
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.391
_diffrn_reflns_theta_min         2.023
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2880
_reflns_number_total             6486
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         6486
_refine_ls_number_restraints     77
_refine_ls_R_factor_all          0.1789
_refine_ls_R_factor_gt           0.0686
_refine_ls_restrained_S_all      0.974
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0974P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1566
_refine_ls_wR_factor_ref         0.2151
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C37-C38 \\sim C37-C36 \\sim C39-C38 \\sim C39-C40 \\sim C41-C40
 with sigma of 0.02
 C44-C40 \\sim C39-C40 \\sim C44-C43 \\sim C39-C38 \\sim C37-C38 \\sim C42-C43
 with sigma of 0.02
3. Rigid bond restraints
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C7, C21
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C36) \\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C39)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C42) \\sim Ueq, Uanis(C43) \\sim Ueq, Uanis(C44) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
Uanis(C21) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
5. Others
 Fixed Sof: H36A(0.6) H36B(0.6) H36C(0.4) H36D(0.4) C37(0.6) H37A(0.6)
 H37B(0.6) C38(0.6) H38A(0.6) H38B(0.6) C39(0.6) H39A(0.6) H39B(0.6) H40A(0.6)
 H40B(0.6) H40C(0.4) H40D(0.4) C42(0.4) H42A(0.4) H42B(0.4) C43(0.4) H43A(0.4)
 H43B(0.4) C44(0.4) H44A(0.4) H44B(0.4)
6.a Secondary CH2 refined with riding coordinates:
 C36(H36A,H36B), C36(H36C,H36D), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,
 H39B), C40(H40A,H40B), C40(H40C,H40D), C42(H42A,H42B), C43(H43A,H43B),
 C44(H44A,H44B)
6.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22),
  C23(H23), C25(H25), C26(H26), C28(H28), C31(H31), C32(H32), C34(H34), C35(H35)
6.c Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.2795(3) 0.1917(2) 0.65107(13) 0.0558(7) Uani 1 1 d . . . . .
F2 F 0.4836(3) 0.2336(2) 0.56331(15) 0.0632(7) Uani 1 1 d . . . . .
O1 O 0.3783(3) 0.4016(2) 0.62626(17) 0.0519(8) Uani 1 1 d . . . . .
O2 O 0.2586(3) 0.3165(2) 0.53024(15) 0.0452(7) Uani 1 1 d . . . . .
O3 O -0.0640(3) 0.4929(3) 0.24009(15) 0.0549(8) Uani 1 1 d . . . . .
C1 C 0.7359(4) 1.0165(3) 0.6145(2) 0.0353(9) Uani 1 1 d . . . . .
H1 H 0.6557 1.0182 0.5860 0.042 Uiso 1 1 calc R . . . .
C2 C 0.8725(4) 1.0551(3) 0.5764(2) 0.0419(10) Uani 1 1 d . . . . .
H2 H 0.8855 1.0854 0.5221 0.050 Uiso 1 1 calc R . . . .
C3 C 0.9917(4) 1.0503(4) 0.6167(2) 0.0426(10) Uani 1 1 d . . . . .
H3 H 1.0868 1.0760 0.5902 0.051 Uiso 1 1 calc R . . . .
C4 C 0.9705(4) 1.0077(4) 0.6959(2) 0.0438(10) Uani 1 1 d . . . . .
H4 H 1.0514 1.0054 0.7240 0.053 Uiso 1 1 calc R . . . .
C5 C 0.8342(4) 0.9687(4) 0.7340(2) 0.0381(9) Uani 1 1 d . . . . .
H5 H 0.8220 0.9373 0.7881 0.046 Uiso 1 1 calc R . . . .
C6 C 0.7124(4) 0.9747(3) 0.6939(2) 0.0295(8) Uani 1 1 d . . . . .
C7 C 0.5607(4) 0.9329(3) 0.7324(2) 0.0357(9) Uani 1 1 d . U . . .
C8 C 0.4900(4) 0.9836(3) 0.7926(2) 0.0363(9) Uani 1 1 d . . . . .
C9 C 0.5647(4) 1.0858(3) 0.8255(2) 0.0352(9) Uani 1 1 d . . . . .
C10 C 0.5980(4) 1.2118(3) 0.7838(2) 0.0398(10) Uani 1 1 d . . . . .
H10 H 0.5726 1.2368 0.7332 0.048 Uiso 1 1 calc R . . . .
C11 C 0.6682(5) 1.3010(4) 0.8162(3) 0.0510(11) Uani 1 1 d . . . . .
H11 H 0.6917 1.3869 0.7874 0.061 Uiso 1 1 calc R . . . .
C12 C 0.7044(5) 1.2663(4) 0.8899(3) 0.0544(12) Uani 1 1 d . . . . .
H12 H 0.7535 1.3278 0.9115 0.065 Uiso 1 1 calc R . . . .
C13 C 0.6689(4) 1.1413(4) 0.9322(2) 0.0504(11) Uani 1 1 d . . . . .
H13 H 0.6933 1.1171 0.9831 0.060 Uiso 1 1 calc R . . . .
C14 C 0.5983(4) 1.0526(4) 0.9004(2) 0.0396(9) Uani 1 1 d . . . . .
H14 H 0.5722 0.9677 0.9299 0.048 Uiso 1 1 calc R . . . .
C15 C 0.3365(4) 0.9464(4) 0.8311(2) 0.0351(9) Uani 1 1 d . . . . .
C16 C 0.2441(4) 1.0465(4) 0.8534(2) 0.0433(10) Uani 1 1 d . . . . .
H16 H 0.2791 1.1351 0.8438 0.052 Uiso 1 1 calc R . . . .
C17 C 0.1006(4) 1.0195(4) 0.8897(2) 0.0499(11) Uani 1 1 d . . . . .
H17 H 0.0386 1.0898 0.9043 0.060 Uiso 1 1 calc R . . . .
C18 C 0.0479(4) 0.8928(4) 0.9046(2) 0.0496(11) Uani 1 1 d . . . . .
H18 H -0.0504 0.8744 0.9289 0.060 Uiso 1 1 calc R . . . .
C19 C 0.1387(5) 0.7938(4) 0.8838(3) 0.0619(13) Uani 1 1 d . . . . .
H19 H 0.1030 0.7054 0.8944 0.074 Uiso 1 1 calc R . . . .
C20 C 0.2824(5) 0.8180(4) 0.8476(2) 0.0515(11) Uani 1 1 d . . . . .
H20 H 0.3436 0.7465 0.8341 0.062 Uiso 1 1 calc R . . . .
C21 C 0.4947(4) 0.8285(3) 0.6979(2) 0.0308(8) Uani 1 1 d . U . . .
C22 C 0.5562(4) 0.7018(3) 0.7088(2) 0.0369(9) Uani 1 1 d . . . . .
H22 H 0.6336 0.6834 0.7395 0.044 Uiso 1 1 calc R . . . .
C23 C 0.5074(4) 0.6021(3) 0.6759(2) 0.0347(9) Uani 1 1 d . . . . .
H23 H 0.5496 0.5156 0.6849 0.042 Uiso 1 1 calc R . . . .
C24 C 0.3960(4) 0.6284(3) 0.6293(2) 0.0349(9) Uani 1 1 d . . . . .
C25 C 0.3356(4) 0.7564(3) 0.6173(2) 0.0412(10) Uani 1 1 d . . . . .
H25 H 0.2611 0.7763 0.5849 0.049 Uiso 1 1 calc R . . . .
C26 C 0.3833(4) 0.8542(3) 0.6521(2) 0.0394(9) Uani 1 1 d . . . . .
H26 H 0.3394 0.9401 0.6445 0.047 Uiso 1 1 calc R . . . .
C27 C 0.3507(4) 0.5221(3) 0.5918(2) 0.0383(9) Uani 1 1 d . . . . .
C28 C 0.2822(4) 0.5433(3) 0.5270(2) 0.0388(9) Uani 1 1 d . . . . .
H28 H 0.2675 0.6316 0.5017 0.047 Uiso 1 1 calc R . . . .
C29 C 0.2343(4) 0.4388(3) 0.4980(2) 0.0328(9) Uani 1 1 d . . . . .
C30 C 0.1523(4) 0.4541(3) 0.4328(2) 0.0304(8) Uani 1 1 d . . . . .
C31 C 0.1064(4) 0.5795(3) 0.3977(2) 0.0372(9) Uani 1 1 d . . . . .
H31 H 0.1274 0.6553 0.4182 0.045 Uiso 1 1 calc R . . . .
C32 C 0.0322(4) 0.5965(4) 0.3349(2) 0.0416(10) Uani 1 1 d . . . . .
H32 H 0.0015 0.6825 0.3127 0.050 Uiso 1 1 calc R . . . .
C33 C 0.0027(4) 0.4860(4) 0.3040(2) 0.0387(9) Uani 1 1 d . . . . .
C34 C 0.0451(4) 0.3601(3) 0.3379(2) 0.0383(9) Uani 1 1 d . . . . .
H34 H 0.0246 0.2846 0.3169 0.046 Uiso 1 1 calc R . . . .
C35 C 0.1169(4) 0.3448(3) 0.4018(2) 0.0379(9) Uani 1 1 d . . . . .
H35 H 0.1430 0.2581 0.4254 0.045 Uiso 1 1 calc R . . . .
C36 C -0.1044(7) 0.6222(5) 0.2029(3) 0.0785(16) Uani 1 1 d D U . . .
H36A H -0.0274 0.6871 0.2041 0.094 Uiso 0.6 1 calc R . P A 1
H36B H -0.1986 0.6512 0.2302 0.094 Uiso 0.6 1 calc R . P A 1
H36C H -0.0189 0.6692 0.1701 0.094 Uiso 0.4 1 calc R . P B 2
H36D H -0.1495 0.6773 0.2408 0.094 Uiso 0.4 1 calc R . P B 2
C37 C -0.1210(7) 0.6153(7) 0.1195(4) 0.0410(16) Uani 0.6 1 d D U P C 1
H37A H -0.1151 0.7055 0.0880 0.049 Uiso 0.6 1 calc R . P C 1
H37B H -0.0407 0.5602 0.0973 0.049 Uiso 0.6 1 calc R . P C 1
C38 C -0.2695(8) 0.5545(8) 0.1189(4) 0.045(2) Uani 0.6 1 d D U P C 1
H38A H -0.3487 0.6112 0.1405 0.054 Uiso 0.6 1 calc R . P C 1
H38B H -0.2756 0.4661 0.1525 0.054 Uiso 0.6 1 calc R . P C 1
C39 C -0.2945(9) 0.5396(6) 0.0381(4) 0.0501(18) Uani 0.6 1 d D U P C 1
H39A H -0.2093 0.4908 0.0151 0.060 Uiso 0.6 1 calc R . P C 1
H39B H -0.3829 0.4842 0.0426 0.060 Uiso 0.6 1 calc R . P C 1
C40 C -0.3147(6) 0.6644(4) -0.0161(3) 0.0658(13) Uani 1 1 d D . . . .
H40A H -0.2293 0.7221 -0.0178 0.079 Uiso 0.6 1 calc R . P C 1
H40B H -0.4036 0.7104 0.0055 0.079 Uiso 0.6 1 calc R . P C 1
H40C H -0.2823 0.7545 -0.0133 0.079 Uiso 0.4 1 calc R . P C 2
H40D H -0.4090 0.6450 0.0186 0.079 Uiso 0.4 1 calc R . P C 2
C41 C -0.3305(7) 0.6526(5) -0.0977(3) 0.0917(19) Uani 1 1 d D . . . .
H41A H -0.2416 0.6107 -0.1211 0.138 Uiso 1 1 calc GR . . . .
H41B H -0.3436 0.7412 -0.1277 0.138 Uiso 1 1 calc GR . . . .
H41C H -0.4165 0.5982 -0.0975 0.138 Uiso 1 1 calc GR . . . .
C42 C -0.2326(15) 0.5805(13) 0.1477(6) 0.053(3) Uani 0.4 1 d D U P C 2
H42A H -0.2734 0.4905 0.1672 0.064 Uiso 0.4 1 calc R . P C 2
H42B H -0.3138 0.6465 0.1429 0.064 Uiso 0.4 1 calc R . P C 2
C43 C -0.1284(13) 0.5871(12) 0.0748(6) 0.062(3) Uani 0.4 1 d D U P C 2
H43A H -0.0492 0.5201 0.0835 0.075 Uiso 0.4 1 calc R . P C 2
H43B H -0.0818 0.6756 0.0620 0.075 Uiso 0.4 1 calc R . P C 2
C44 C -0.1998(13) 0.5629(11) 0.0049(7) 0.062(3) Uani 0.4 1 d D U P C 2
H44A H -0.1220 0.5637 -0.0401 0.075 Uiso 0.4 1 calc R . P C 2
H44B H -0.2452 0.4738 0.0171 0.075 Uiso 0.4 1 calc R . P C 2
B1 B 0.3522(5) 0.2831(4) 0.5931(3) 0.0443(12) 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
F1 B1 1.371(5) . ?
F2 B1 1.363(5) . ?
O1 C27 1.310(4) . ?
O1 B1 1.479(5) . ?
O2 C29 1.306(4) . ?
O2 B1 1.490(5) . ?
O3 C33 1.355(4) . ?
O3 C36 1.432(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.369(5) . ?
C1 C6 1.386(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.368(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.402(5) . ?
C6 C7 1.498(5) . ?
C7 C8 1.343(5) . ?
C7 C21 1.505(5) . ?
C8 C9 1.511(5) . ?
C8 C15 1.502(5) . ?
C9 C10 1.388(5) . ?
C9 C14 1.391(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.381(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.374(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(5) . ?
C15 C20 1.387(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.393(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.367(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.356(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.389(5) . ?
C21 C26 1.385(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.378(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.395(5) . ?
C24 C25 1.397(5) . ?
C24 C27 1.473(5) . ?
C25 H25 0.9500 . ?
C25 C26 1.378(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.369(5) . ?
C28 H28 0.9500 . ?
C28 C29 1.377(5) . ?
C29 C30 1.452(5) . ?
C30 C31 1.402(5) . ?
C30 C35 1.397(5) . ?
C31 H31 0.9500 . ?
C31 C32 1.372(5) . ?
C32 H32 0.9500 . ?
C32 C33 1.391(5) . ?
C33 C34 1.390(5) . ?
C34 H34 0.9500 . ?
C34 C35 1.375(5) . ?
C35 H35 0.9500 . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C36 H36C 0.9900 . ?
C36 H36D 0.9900 . ?
C36 C37 1.525(7) . ?
C36 C42 1.743(14) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C37 C38 1.518(8) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C38 C39 1.520(8) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C39 C40 1.479(7) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C40 H40C 0.9900 . ?
C40 H40D 0.9900 . ?
C40 C41 1.503(6) . ?
C40 C44 1.493(10) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C42 C43 1.486(11) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C43 C44 1.545(11) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?

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
C27 O1 B1 122.0(3) . . ?
C29 O2 B1 122.4(3) . . ?
C33 O3 C36 117.1(3) . . ?
C2 C1 H1 119.3 . . ?
C2 C1 C6 121.4(4) . . ?
C6 C1 H1 119.3 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.2(4) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.2(4) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(4) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 117.9(3) . . ?
C1 C6 C7 119.0(3) . . ?
C5 C6 C7 123.1(3) . . ?
C6 C7 C21 114.1(3) . . ?
C8 C7 C6 123.0(3) . . ?
C8 C7 C21 122.9(3) . . ?
C7 C8 C9 120.0(3) . . ?
C7 C8 C15 124.3(3) . . ?
C15 C8 C9 115.6(3) . . ?
C10 C9 C8 122.2(3) . . ?
C10 C9 C14 119.3(4) . . ?
C14 C9 C8 118.6(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.8(4) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(4) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.8(4) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.8(4) . . ?
C14 C13 H13 120.1 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.7(4) . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C8 117.8(3) . . ?
C16 C15 C20 117.8(3) . . ?
C20 C15 C8 124.5(3) . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.0(3) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.6(4) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.7 . . ?
C19 C18 C17 118.7(4) . . ?
C19 C18 H18 120.7 . . ?
C18 C19 H19 119.1 . . ?
C18 C19 C20 121.9(4) . . ?
C20 C19 H19 119.1 . . ?
C15 C20 C19 120.1(4) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C22 C21 C7 117.6(3) . . ?
C26 C21 C7 123.6(3) . . ?
C26 C21 C22 118.7(3) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.4(3) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C24 119.9(3) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C25 118.8(3) . . ?
C23 C24 C27 118.9(3) . . ?
C25 C24 C27 122.2(3) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.6(3) . . ?
C26 C25 H25 119.7 . . ?
C21 C26 H26 119.7 . . ?
C25 C26 C21 120.7(3) . . ?
C25 C26 H26 119.7 . . ?
O1 C27 C24 114.6(3) . . ?
O1 C27 C28 121.0(3) . . ?
C28 C27 C24 124.4(3) . . ?
C27 C28 H28 119.4 . . ?
C27 C28 C29 121.1(3) . . ?
C29 C28 H28 119.4 . . ?
O2 C29 C28 120.3(3) . . ?
O2 C29 C30 115.6(3) . . ?
C28 C29 C30 124.0(3) . . ?
C31 C30 C29 121.4(3) . . ?
C35 C30 C29 121.5(3) . . ?
C35 C30 C31 117.1(3) . . ?
C30 C31 H31 118.9 . . ?
C32 C31 C30 122.3(3) . . ?
C32 C31 H31 118.9 . . ?
C31 C32 H32 120.4 . . ?
C31 C32 C33 119.1(3) . . ?
C33 C32 H32 120.4 . . ?
O3 C33 C32 123.7(3) . . ?
O3 C33 C34 116.3(3) . . ?
C34 C33 C32 120.1(3) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 C33 119.9(3) . . ?
C35 C34 H34 120.0 . . ?
C30 C35 H35 119.3 . . ?
C34 C35 C30 121.4(3) . . ?
C34 C35 H35 119.3 . . ?
O3 C36 H36A 110.0 . . ?
O3 C36 H36B 110.0 . . ?
O3 C36 H36C 111.7 . . ?
O3 C36 H36D 111.7 . . ?
O3 C36 C37 108.4(4) . . ?
O3 C36 C42 100.5(5) . . ?
H36A C36 H36B 108.4 . . ?
H36C C36 H36D 109.4 . . ?
C37 C36 H36A 110.0 . . ?
C37 C36 H36B 110.0 . . ?
C42 C36 H36C 111.7 . . ?
C42 C36 H36D 111.7 . . ?
C36 C37 H37A 110.0 . . ?
C36 C37 H37B 110.0 . . ?
H37A C37 H37B 108.4 . . ?
C38 C37 C36 108.4(6) . . ?
C38 C37 H37A 110.0 . . ?
C38 C37 H37B 110.0 . . ?
C37 C38 H38A 109.1 . . ?
C37 C38 H38B 109.1 . . ?
C37 C38 C39 112.3(6) . . ?
H38A C38 H38B 107.9 . . ?
C39 C38 H38A 109.1 . . ?
C39 C38 H38B 109.1 . . ?
C38 C39 H39A 108.2 . . ?
C38 C39 H39B 108.2 . . ?
H39A C39 H39B 107.4 . . ?
C40 C39 C38 116.1(6) . . ?
C40 C39 H39A 108.2 . . ?
C40 C39 H39B 108.2 . . ?
C39 C40 H40A 108.0 . . ?
C39 C40 H40B 108.0 . . ?
C39 C40 C41 117.1(4) . . ?
H40A C40 H40B 107.3 . . ?
H40C C40 H40D 109.0 . . ?
C41 C40 H40A 108.0 . . ?
C41 C40 H40B 108.0 . . ?
C41 C40 H40C 111.0 . . ?
C41 C40 H40D 111.0 . . ?
C44 C40 H40C 111.0 . . ?
C44 C40 H40D 111.0 . . ?
C44 C40 C41 103.8(6) . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C36 C42 H42A 112.5 . . ?
C36 C42 H42B 112.5 . . ?
H42A C42 H42B 110.1 . . ?
C43 C42 C36 96.0(9) . . ?
C43 C42 H42A 112.5 . . ?
C43 C42 H42B 112.5 . . ?
C42 C43 H43A 108.7 . . ?
C42 C43 H43B 108.7 . . ?
C42 C43 C44 114.4(10) . . ?
H43A C43 H43B 107.6 . . ?
C44 C43 H43A 108.7 . . ?
C44 C43 H43B 108.7 . . ?
C40 C44 C43 112.8(9) . . ?
C40 C44 H44A 109.0 . . ?
C40 C44 H44B 109.0 . . ?
C43 C44 H44A 109.0 . . ?
C43 C44 H44B 109.0 . . ?
H44A C44 H44B 107.8 . . ?
F1 B1 O1 107.8(4) . . ?
F1 B1 O2 108.6(3) . . ?
F2 B1 F1 111.2(3) . . ?
F2 B1 O1 109.5(3) . . ?
F2 B1 O2 108.6(4) . . ?
O1 B1 O2 111.2(3) . . ?

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 C27 C28 C29 2.9(6) . . . . ?
O2 C29 C30 C31 173.7(3) . . . . ?
O2 C29 C30 C35 -6.8(5) . . . . ?
O3 C33 C34 C35 178.3(3) . . . . ?
O3 C36 C37 C38 78.8(6) . . . . ?
O3 C36 C42 C43 -97.1(8) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
C1 C6 C7 C8 -127.1(4) . . . . ?
C1 C6 C7 C21 53.3(4) . . . . ?
C2 C1 C6 C5 -2.2(5) . . . . ?
C2 C1 C6 C7 -179.7(3) . . . . ?
C2 C3 C4 C5 1.0(6) . . . . ?
C3 C4 C5 C6 -1.8(6) . . . . ?
C4 C5 C6 C1 2.4(5) . . . . ?
C4 C5 C6 C7 179.7(3) . . . . ?
C5 C6 C7 C8 55.6(5) . . . . ?
C5 C6 C7 C21 -124.0(4) . . . . ?
C6 C1 C2 C3 1.5(5) . . . . ?
C6 C7 C8 C9 -1.1(5) . . . . ?
C6 C7 C8 C15 178.3(3) . . . . ?
C6 C7 C21 C22 69.4(4) . . . . ?
C6 C7 C21 C26 -106.2(4) . . . . ?
C7 C8 C9 C10 66.4(5) . . . . ?
C7 C8 C9 C14 -114.8(4) . . . . ?
C7 C8 C15 C16 -140.0(4) . . . . ?
C7 C8 C15 C20 41.8(6) . . . . ?
C7 C21 C22 C23 -176.7(3) . . . . ?
C7 C21 C26 C25 174.9(3) . . . . ?
C8 C7 C21 C22 -110.3(4) . . . . ?
C8 C7 C21 C26 74.1(5) . . . . ?
C8 C9 C10 C11 -179.1(3) . . . . ?
C8 C9 C14 C13 178.7(3) . . . . ?
C8 C15 C16 C17 -179.7(4) . . . . ?
C8 C15 C20 C19 179.6(4) . . . . ?
C9 C8 C15 C16 39.5(5) . . . . ?
C9 C8 C15 C20 -138.8(4) . . . . ?
C9 C10 C11 C12 -0.6(6) . . . . ?
C10 C9 C14 C13 -2.5(6) . . . . ?
C10 C11 C12 C13 -0.6(6) . . . . ?
C11 C12 C13 C14 0.2(6) . . . . ?
C12 C13 C14 C9 1.3(6) . . . . ?
C14 C9 C10 C11 2.1(5) . . . . ?
C15 C8 C9 C10 -113.1(4) . . . . ?
C15 C8 C9 C14 65.7(4) . . . . ?
C15 C16 C17 C18 0.4(6) . . . . ?
C16 C15 C20 C19 1.4(6) . . . . ?
C16 C17 C18 C19 0.6(6) . . . . ?
C17 C18 C19 C20 -0.5(7) . . . . ?
C18 C19 C20 C15 -0.5(7) . . . . ?
C20 C15 C16 C17 -1.4(6) . . . . ?
C21 C7 C8 C9 178.5(3) . . . . ?
C21 C7 C8 C15 -2.1(5) . . . . ?
C21 C22 C23 C24 1.3(5) . . . . ?
C22 C21 C26 C25 -0.7(5) . . . . ?
C22 C23 C24 C25 -0.2(5) . . . . ?
C22 C23 C24 C27 177.1(3) . . . . ?
C23 C24 C25 C26 -1.3(6) . . . . ?
C23 C24 C27 O1 23.9(5) . . . . ?
C23 C24 C27 C28 -157.4(4) . . . . ?
C24 C25 C26 C21 1.8(6) . . . . ?
C24 C27 C28 C29 -175.7(3) . . . . ?
C25 C24 C27 O1 -158.9(4) . . . . ?
C25 C24 C27 C28 19.8(6) . . . . ?
C26 C21 C22 C23 -0.9(5) . . . . ?
C27 O1 B1 F1 -133.4(4) . . . . ?
C27 O1 B1 F2 105.5(4) . . . . ?
C27 O1 B1 O2 -14.5(5) . . . . ?
C27 C24 C25 C26 -178.5(4) . . . . ?
C27 C28 C29 O2 -2.7(6) . . . . ?
C27 C28 C29 C30 175.7(3) . . . . ?
C28 C29 C30 C31 -4.7(6) . . . . ?
C28 C29 C30 C35 174.7(3) . . . . ?
C29 O2 B1 F1 133.2(3) . . . . ?
C29 O2 B1 F2 -105.8(4) . . . . ?
C29 O2 B1 O1 14.7(5) . . . . ?
C29 C30 C31 C32 178.3(3) . . . . ?
C29 C30 C35 C34 -177.0(3) . . . . ?
C30 C31 C32 C33 -0.8(6) . . . . ?
C31 C30 C35 C34 2.4(5) . . . . ?
C31 C32 C33 O3 -177.0(3) . . . . ?
C31 C32 C33 C34 1.5(6) . . . . ?
C32 C33 C34 C35 -0.3(6) . . . . ?
C33 O3 C36 C37 158.6(4) . . . . ?
C33 O3 C36 C42 -161.8(5) . . . . ?
C33 C34 C35 C30 -1.7(6) . . . . ?
C35 C30 C31 C32 -1.1(5) . . . . ?
C36 O3 C33 C32 0.5(6) . . . . ?
C36 O3 C33 C34 -178.1(4) . . . . ?
C36 C37 C38 C39 -178.3(5) . . . . ?
C36 C42 C43 C44 -176.9(9) . . . . ?
C37 C38 C39 C40 -69.0(9) . . . . ?
C38 C39 C40 C41 176.4(6) . . . . ?
C41 C40 C44 C43 161.0(8) . . . . ?
C42 C43 C44 C40 62.0(14) . . . . ?
B1 O1 C27 C24 -174.7(3) . . . . ?
B1 O1 C27 C28 6.6(6) . . . . ?
B1 O2 C29 C28 -7.0(6) . . . . ?
B1 O2 C29 C30 174.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
