# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_2_erk10103
_database_code_depnum_ccdc_archive 'CCDC 2157861'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2022-03-11 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2019.11-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H27 B F5 N3 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         587.38

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.5951(4)
_cell_length_b                   13.5070(7)
_cell_length_c                   25.5281(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.612(3)
_cell_angle_gamma                90
_cell_volume                     2922.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3651
_cell_measurement_theta_min      3.5120
_cell_measurement_theta_max      65.6762
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1216

_exptl_absorpt_coefficient_mu    0.868
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption
correction. Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M.
& Stalke D., J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu sealed tube'
_diffrn_source_type              'fine-focus sealed tube'
_diffrn_source_power             1.50
_diffrn_source_current           30.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device       'Bruker APEXII Diffractometer'
_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            35334
_diffrn_reflns_av_R_equivalents  0.1034
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_theta_min         3.51
_diffrn_reflns_theta_max         66.77
_diffrn_reflns_theta_full        66.77
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30

_refine_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_number_total             5118
_reflns_number_gt                3320
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1453
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_number_reflns         5118
_refine_ls_number_parameters     394
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0740P)²+0.1218P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.270
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00139(18)

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'
N N 0.0311 0.0180 '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'

_computing_data_collection       'Bruker APEX3 v2019.11-0 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.4297(4) 0.3420(2) 0.62516(11) 0.0282(7) Uani d . . . 1 . .
N N1 0.3620(2) 0.48409(15) 0.55335(7) 0.0248(5) Uani d . . . 1 . .
N N2 0.4763(2) 0.53769(16) 0.63024(7) 0.0258(5) Uani d . . . 1 . .
N N3 0.5539(2) 0.28648(16) 0.56807(8) 0.0273(5) Uani d . . . 1 . .
O O1 0.5998(2) 0.31743(14) 0.62391(6) 0.0304(4) Uani d . . . 1 . .
C C1 0.4072(3) 0.45693(19) 0.60512(9) 0.0247(6) Uani d . . . 1 . .
C C2 0.4113(3) 0.58035(19) 0.54628(10) 0.0282(6) Uani d . . . 1 . .
H H2 0.398312 0.61583 0.513708 0.034 Uiso calc U . R 1 . .
C C3 0.4812(3) 0.6142(2) 0.59427(9) 0.0291(6) Uani d . . . 1 . .
H H3 0.525289 0.678177 0.601924 0.035 Uiso calc U . R 1 . .
C C11 0.2666(3) 0.42036(19) 0.51494(9) 0.0242(6) Uani d . . . 1 . .
C C12 0.2738(3) 0.3185(2) 0.52488(9) 0.0267(6) Uani d . . . 1 . .
C C13 0.1747(3) 0.2557(2) 0.49149(10) 0.0302(6) Uani d . . . 1 . .
H H13 0.17913 0.186517 0.498375 0.036 Uiso calc U . R 1 . .
C C14 0.0690(3) 0.2911(2) 0.44821(10) 0.0322(6) Uani d . . . 1 . .
C C15 0.0671(3) 0.3920(2) 0.43937(9) 0.0303(6) Uani d . . . 1 . .
H H15 -0.002851 0.416951 0.40953 0.036 Uiso calc U . R 1 . .
C C16 0.1617(3) 0.4594(2) 0.47167(9) 0.0261(6) Uani d . . . 1 . .
C C17 0.3816(3) 0.2765(2) 0.57159(9) 0.0263(6) Uani d . . . 1 . .
H H17 0.352756 0.207004 0.579581 0.032 Uiso calc U . R 1 . .
C C18 -0.0411(4) 0.2214(2) 0.41346(11) 0.0441(8) Uani d . . . 1 . .
H H18A -0.144011 0.220908 0.425176 0.066 Uiso calc U . R 1 . .
H H18B 0.003456 0.154447 0.416237 0.066 Uiso calc U . R 1 . .
H H18C -0.054016 0.2437 0.376458 0.066 Uiso calc U . R 1 . .
C C19 0.1416(3) 0.5679(2) 0.45765(10) 0.0316(6) Uani d . . . 1 . .
H H19A 0.139102 0.606467 0.490025 0.047 Uiso calc U . R 1 . .
H H19B 0.042463 0.577508 0.432959 0.047 Uiso calc U . R 1 . .
H H19C 0.230067 0.590122 0.440887 0.047 Uiso calc U . R 1 . .
C C21 0.5261(3) 0.54291(19) 0.68723(9) 0.0257(6) Uani d . . . 1 . .
C C22 0.6842(3) 0.5270(2) 0.70900(10) 0.0308(6) Uani d . . . 1 . .
C C23 0.7224(3) 0.5272(2) 0.76400(10) 0.0355(7) Uani d . . . 1 . .
H H23 0.82958 0.517696 0.779698 0.043 Uiso calc U . R 1 . .
C C24 0.6122(4) 0.5404(2) 0.79701(10) 0.0363(7) Uani d . . . 1 . .
C C25 0.4568(3) 0.5598(2) 0.77360(10) 0.0311(6) Uani d . . . 1 . .
H H25 0.380359 0.572185 0.795721 0.037 Uiso calc U . R 1 . .
C C26 0.4107(3) 0.56156(19) 0.71868(9) 0.0277(6) Uani d . . . 1 . .
C C27 0.8064(3) 0.5075(3) 0.67474(11) 0.0415(7) Uani d . . . 1 . .
H H27A 0.911498 0.508629 0.696661 0.062 Uiso calc U . R 1 . .
H H27B 0.800096 0.558735 0.647277 0.062 Uiso calc U . R 1 . .
H H27C 0.787575 0.442463 0.657883 0.062 Uiso calc U . R 1 . .
C C28 0.6566(4) 0.5336(2) 0.85657(10) 0.0519(9) Uani d . . . 1 . .
H H28A 0.566635 0.553891 0.873126 0.078 Uiso calc U . R 1 . .
H H28B 0.746424 0.577348 0.868615 0.078 Uiso calc U . R 1 . .
H H28C 0.685515 0.465234 0.866692 0.078 Uiso calc U . R 1 . .
C C29 0.2426(3) 0.5823(2) 0.69459(11) 0.0381(7) Uani d . . . 1 . .
H H29A 0.239327 0.635463 0.668282 0.057 Uiso calc U . R 1 . .
H H29B 0.183753 0.602772 0.722519 0.057 Uiso calc U . R 1 . .
H H29C 0.194761 0.522382 0.677232 0.057 Uiso calc U . R 1 . .
C C31 0.3730(3) 0.3189(2) 0.68095(10) 0.0285(6) Uani d . . . 1 . .
C C32 0.2160(3) 0.3117(2) 0.68492(11) 0.0368(7) Uani d . . . 1 . .
C C33 0.1604(4) 0.2934(3) 0.73151(12) 0.0463(8) Uani d . . . 1 . .
C C34 0.2676(4) 0.2842(2) 0.77789(11) 0.0465(8) Uani d . . . 1 . .
C C35 0.4249(4) 0.2911(2) 0.77651(10) 0.0380(7) Uani d . . . 1 . .
C C36 0.4747(3) 0.3066(2) 0.72882(10) 0.0320(6) Uani d . . . 1 . .
C C41 0.6394(3) 0.2022(2) 0.55666(11) 0.0323(6) Uani d . . . 1 . .
C C42 0.5864(4) 0.1479(2) 0.51144(12) 0.0442(8) Uani d . . . 1 . .
H H42 0.488959 0.164253 0.489728 0.053 Uiso calc U . R 1 . .
C C43 0.6756(5) 0.0690(2) 0.49761(15) 0.0570(10) Uani d . . . 1 . .
H H43 0.638503 0.031393 0.466589 0.068 Uiso calc U . R 1 . .
C C44 0.8165(5) 0.0454(3) 0.52850(19) 0.0705(12) Uani d . . . 1 . .
H H44 0.877375 -0.008282 0.518931 0.085 Uiso calc U . R 1 . .
C C45 0.8690(4) 0.0992(3) 0.5729(2) 0.0732(13) Uani d . . . 1 . .
H H45 0.967249 0.082475 0.594021 0.088 Uiso calc U . R 1 . .
C C46 0.7823(4) 0.1784(2) 0.58843(15) 0.0518(9) Uani d . . . 1 . .
H H46 0.819846 0.214923 0.619789 0.062 Uiso calc U . R 1 . .
F F32 0.10710(19) 0.32117(15) 0.63987(6) 0.0488(5) Uani d . . . 1 . .
F F33 0.0044(2) 0.28465(19) 0.73231(8) 0.0753(7) Uani d . . . 1 . .
F F34 0.2161(3) 0.26746(16) 0.82432(7) 0.0672(6) Uani d . . . 1 . .
F F35 0.5288(2) 0.28380(13) 0.82207(6) 0.0512(5) Uani d . . . 1 . .
F F36 0.63234(19) 0.30956(13) 0.73040(6) 0.0414(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 O1 . 1.505(4) ?
B1 C31 . 1.611(4) ?
B1 C17 . 1.624(4) ?
B1 C1 . 1.636(4) ?
N1 C1 . 1.364(3) ?
N1 C2 . 1.389(3) ?
N1 C11 . 1.451(3) ?
N2 C1 . 1.352(3) ?
N2 C3 . 1.388(3) ?
N2 C21 . 1.448(3) ?
N3 C41 . 1.411(3) ?
N3 O1 . 1.475(3) ?
N3 C17 . 1.504(3) ?
C2 C3 . 1.351(4) ?
C2 H2 . 0.95 ?
C3 H3 . 0.95 ?
C11 C12 . 1.399(4) ?
C11 C16 . 1.406(3) ?
C12 C13 . 1.389(4) ?
C12 C17 . 1.495(3) ?
C13 C14 . 1.393(4) ?
C13 H13 . 0.95 ?
C14 C15 . 1.381(4) ?
C14 C18 . 1.512(4) ?
C15 C16 . 1.395(4) ?
C15 H15 . 0.95 ?
C16 C19 . 1.512(4) ?
C17 H17 . 1.0 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C21 C22 . 1.396(4) ?
C21 C26 . 1.399(4) ?
C22 C23 . 1.387(4) ?
C22 C27 . 1.498(4) ?
C23 C24 . 1.380(4) ?
C23 H23 . 0.95 ?
C24 C25 . 1.394(4) ?
C24 C28 . 1.507(4) ?
C25 C26 . 1.392(3) ?
C25 H25 . 0.95 ?
C26 C29 . 1.500(4) ?
C27 H27A . 0.98 ?
C27 H27B . 0.98 ?
C27 H27C . 0.98 ?
C28 H28A . 0.98 ?
C28 H28B . 0.98 ?
C28 H28C . 0.98 ?
C29 H29A . 0.98 ?
C29 H29B . 0.98 ?
C29 H29C . 0.98 ?
C31 C32 . 1.374(4) ?
C31 C36 . 1.389(4) ?
C32 F32 . 1.362(3) ?
C32 C33 . 1.376(4) ?
C33 F33 . 1.350(4) ?
C33 C34 . 1.379(5) ?
C34 F34 . 1.352(3) ?
C34 C35 . 1.361(5) ?
C35 F35 . 1.346(3) ?
C35 C36 . 1.372(4) ?
C36 F36 . 1.350(3) ?
C41 C42 . 1.380(4) ?
C41 C46 . 1.392(4) ?
C42 C43 . 1.392(4) ?
C42 H42 . 0.95 ?
C43 C44 . 1.368(5) ?
C43 H43 . 0.95 ?
C44 C45 . 1.358(6) ?
C44 H44 . 0.95 ?
C45 C46 . 1.399(5) ?
C45 H45 . 0.95 ?
C46 H46 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 B1 C31 . . 114.5(2) ?
O1 B1 C17 . . 88.46(19) ?
C31 B1 C17 . . 124.5(2) ?
O1 B1 C1 . . 105.5(2) ?
C31 B1 C1 . . 115.0(2) ?
C17 B1 C1 . . 104.7(2) ?
C1 N1 C2 . . 109.5(2) ?
C1 N1 C11 . . 122.2(2) ?
C2 N1 C11 . . 128.2(2) ?
C1 N2 C3 . . 110.29(19) ?
C1 N2 C21 . . 123.3(2) ?
C3 N2 C21 . . 126.3(2) ?
C41 N3 O1 . . 111.32(19) ?
C41 N3 C17 . . 119.4(2) ?
O1 N3 C17 . . 94.28(17) ?
N3 O1 B1 . . 88.81(16) ?
N2 C1 N1 . . 105.9(2) ?
N2 C1 B1 . . 126.7(2) ?
N1 C1 B1 . . 123.9(2) ?
C3 C2 N1 . . 107.4(2) ?
C3 C2 H2 . . 126.3 ?
N1 C2 H2 . . 126.3 ?
C2 C3 N2 . . 106.8(2) ?
C2 C3 H3 . . 126.6 ?
N2 C3 H3 . . 126.6 ?
C12 C11 C16 . . 120.9(2) ?
C12 C11 N1 . . 117.3(2) ?
C16 C11 N1 . . 121.6(2) ?
C13 C12 C11 . . 119.1(2) ?
C13 C12 C17 . . 119.5(2) ?
C11 C12 C17 . . 121.4(2) ?
C12 C13 C14 . . 121.9(3) ?
C12 C13 H13 . . 119.0 ?
C14 C13 H13 . . 119.0 ?
C15 C14 C13 . . 117.2(2) ?
C15 C14 C18 . . 121.9(2) ?
C13 C14 C18 . . 120.9(3) ?
C14 C15 C16 . . 123.9(2) ?
C14 C15 H15 . . 118.1 ?
C16 C15 H15 . . 118.1 ?
C15 C16 C11 . . 117.0(2) ?
C15 C16 C19 . . 117.4(2) ?
C11 C16 C19 . . 125.6(2) ?
C12 C17 N3 . . 113.8(2) ?
C12 C17 B1 . . 120.1(2) ?
N3 C17 B1 . . 83.51(18) ?
C12 C17 H17 . . 112.1 ?
N3 C17 H17 . . 112.1 ?
B1 C17 H17 . . 112.1 ?
C14 C18 H18A . . 109.5 ?
C14 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C14 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C16 C19 H19A . . 109.5 ?
C16 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C16 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C22 C21 C26 . . 122.4(2) ?
C22 C21 N2 . . 119.8(2) ?
C26 C21 N2 . . 117.8(2) ?
C23 C22 C21 . . 116.9(3) ?
C23 C22 C27 . . 121.4(2) ?
C21 C22 C27 . . 121.7(2) ?
C24 C23 C22 . . 123.2(3) ?
C24 C23 H23 . . 118.4 ?
C22 C23 H23 . . 118.4 ?
C23 C24 C25 . . 117.9(2) ?
C23 C24 C28 . . 121.6(3) ?
C25 C24 C28 . . 120.4(3) ?
C26 C25 C24 . . 121.7(3) ?
C26 C25 H25 . . 119.1 ?
C24 C25 H25 . . 119.1 ?
C25 C26 C21 . . 117.7(2) ?
C25 C26 C29 . . 120.6(3) ?
C21 C26 C29 . . 121.7(2) ?
C22 C27 H27A . . 109.5 ?
C22 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C22 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C24 C28 H28A . . 109.5 ?
C24 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C24 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
C26 C29 H29A . . 109.5 ?
C26 C29 H29B . . 109.5 ?
H29A C29 H29B . . 109.5 ?
C26 C29 H29C . . 109.5 ?
H29A C29 H29C . . 109.5 ?
H29B C29 H29C . . 109.5 ?
C32 C31 C36 . . 114.1(2) ?
C32 C31 B1 . . 121.7(2) ?
C36 C31 B1 . . 124.2(2) ?
F32 C32 C31 . . 118.4(2) ?
F32 C32 C33 . . 117.3(3) ?
C31 C32 C33 . . 124.3(3) ?
F33 C33 C32 . . 121.2(3) ?
F33 C33 C34 . . 120.1(3) ?
C32 C33 C34 . . 118.7(3) ?
F34 C34 C35 . . 120.4(3) ?
F34 C34 C33 . . 119.9(3) ?
C35 C34 C33 . . 119.7(3) ?
F35 C35 C34 . . 119.4(3) ?
F35 C35 C36 . . 121.2(3) ?
C34 C35 C36 . . 119.4(3) ?
F36 C36 C35 . . 116.0(2) ?
F36 C36 C31 . . 120.3(2) ?
C35 C36 C31 . . 123.7(3) ?
C42 C41 C46 . . 120.0(3) ?
C42 C41 N3 . . 119.4(3) ?
C46 C41 N3 . . 120.4(3) ?
C41 C42 C43 . . 120.0(3) ?
C41 C42 H42 . . 120.0 ?
C43 C42 H42 . . 120.0 ?
C44 C43 C42 . . 120.3(3) ?
C44 C43 H43 . . 119.9 ?
C42 C43 H43 . . 119.9 ?
C45 C44 C43 . . 119.7(3) ?
C45 C44 H44 . . 120.1 ?
C43 C44 H44 . . 120.1 ?
C44 C45 C46 . . 121.8(4) ?
C44 C45 H45 . . 119.1 ?
C46 C45 H45 . . 119.1 ?
C41 C46 C45 . . 118.2(3) ?
C41 C46 H46 . . 120.9 ?
C45 C46 H46 . . 120.9 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C41 N3 O1 B1 . . . . -141.7(2) ?
C17 N3 O1 B1 . . . . -17.8(2) ?
C31 B1 O1 N3 . . . . 144.1(2) ?
C17 B1 O1 N3 . . . . 16.41(18) ?
C1 B1 O1 N3 . . . . -88.43(19) ?
C3 N2 C1 N1 . . . . -2.6(3) ?
C21 N2 C1 N1 . . . . 173.3(2) ?
C3 N2 C1 B1 . . . . 156.9(2) ?
C21 N2 C1 B1 . . . . -27.2(4) ?
C2 N1 C1 N2 . . . . 3.2(3) ?
C11 N1 C1 N2 . . . . -172.6(2) ?
C2 N1 C1 B1 . . . . -157.0(2) ?
C11 N1 C1 B1 . . . . 27.2(4) ?
O1 B1 C1 N2 . . . . -65.3(3) ?
C31 B1 C1 N2 . . . . 61.9(3) ?
C17 B1 C1 N2 . . . . -157.8(2) ?
O1 B1 C1 N1 . . . . 90.7(3) ?
C31 B1 C1 N1 . . . . -142.1(2) ?
C17 B1 C1 N1 . . . . -1.8(3) ?
C1 N1 C2 C3 . . . . -2.6(3) ?
C11 N1 C2 C3 . . . . 172.9(2) ?
N1 C2 C3 N2 . . . . 0.9(3) ?
C1 N2 C3 C2 . . . . 1.1(3) ?
C21 N2 C3 C2 . . . . -174.7(2) ?
C1 N1 C11 C12 . . . . -25.1(4) ?
C2 N1 C11 C12 . . . . 159.9(3) ?
C1 N1 C11 C16 . . . . 150.0(2) ?
C2 N1 C11 C16 . . . . -24.9(4) ?
C16 C11 C12 C13 . . . . -0.4(4) ?
N1 C11 C12 C13 . . . . 174.8(2) ?
C16 C11 C12 C17 . . . . -178.3(2) ?
N1 C11 C12 C17 . . . . -3.1(4) ?
C11 C12 C13 C14 . . . . 0.4(4) ?
C17 C12 C13 C14 . . . . 178.3(3) ?
C12 C13 C14 C15 . . . . 0.5(4) ?
C12 C13 C14 C18 . . . . -178.1(3) ?
C13 C14 C15 C16 . . . . -1.3(4) ?
C18 C14 C15 C16 . . . . 177.2(3) ?
C14 C15 C16 C11 . . . . 1.3(4) ?
C14 C15 C16 C19 . . . . -178.0(3) ?
C12 C11 C16 C15 . . . . -0.4(4) ?
N1 C11 C16 C15 . . . . -175.3(2) ?
C12 C11 C16 C19 . . . . 178.8(2) ?
N1 C11 C16 C19 . . . . 3.8(4) ?
C13 C12 C17 N3 . . . . 114.3(3) ?
C11 C12 C17 N3 . . . . -67.8(3) ?
C13 C12 C17 B1 . . . . -149.2(3) ?
C11 C12 C17 B1 . . . . 28.7(4) ?
C41 N3 C17 C12 . . . . -105.9(3) ?
O1 N3 C17 C12 . . . . 136.7(2) ?
C41 N3 C17 B1 . . . . 134.0(2) ?
O1 N3 C17 B1 . . . . 16.56(18) ?
O1 B1 C17 C12 . . . . -130.0(2) ?
C31 B1 C17 C12 . . . . 111.0(3) ?
C1 B1 C17 C12 . . . . -24.4(3) ?
O1 B1 C17 N3 . . . . -16.18(17) ?
C31 B1 C17 N3 . . . . -135.2(3) ?
C1 B1 C17 N3 . . . . 89.4(2) ?
C1 N2 C21 C22 . . . . 99.0(3) ?
C3 N2 C21 C22 . . . . -85.8(3) ?
C1 N2 C21 C26 . . . . -79.4(3) ?
C3 N2 C21 C26 . . . . 95.8(3) ?
C26 C21 C22 C23 . . . . 2.1(4) ?
N2 C21 C22 C23 . . . . -176.2(2) ?
C26 C21 C22 C27 . . . . -179.8(3) ?
N2 C21 C22 C27 . . . . 1.9(4) ?
C21 C22 C23 C24 . . . . 1.2(4) ?
C27 C22 C23 C24 . . . . -177.0(3) ?
C22 C23 C24 C25 . . . . -3.6(4) ?
C22 C23 C24 C28 . . . . 176.0(3) ?
C23 C24 C25 C26 . . . . 2.9(4) ?
C28 C24 C25 C26 . . . . -176.7(3) ?
C24 C25 C26 C21 . . . . 0.1(4) ?
C24 C25 C26 C29 . . . . 179.8(3) ?
C22 C21 C26 C25 . . . . -2.7(4) ?
N2 C21 C26 C25 . . . . 175.7(2) ?
C22 C21 C26 C29 . . . . 177.6(3) ?
N2 C21 C26 C29 . . . . -4.0(4) ?
O1 B1 C31 C32 . . . . -162.4(3) ?
C17 B1 C31 C32 . . . . -56.3(4) ?
C1 B1 C31 C32 . . . . 75.2(3) ?
O1 B1 C31 C36 . . . . 18.9(4) ?
C17 B1 C31 C36 . . . . 125.0(3) ?
C1 B1 C31 C36 . . . . -103.5(3) ?
C36 C31 C32 F32 . . . . -179.0(2) ?
B1 C31 C32 F32 . . . . 2.2(4) ?
C36 C31 C32 C33 . . . . -0.3(5) ?
B1 C31 C32 C33 . . . . -179.1(3) ?
F32 C32 C33 F33 . . . . 0.4(5) ?
C31 C32 C33 F33 . . . . -178.3(3) ?
F32 C32 C33 C34 . . . . -179.5(3) ?
C31 C32 C33 C34 . . . . 1.9(5) ?
F33 C33 C34 F34 . . . . -0.7(5) ?
C32 C33 C34 F34 . . . . 179.2(3) ?
F33 C33 C34 C35 . . . . 178.6(3) ?
C32 C33 C34 C35 . . . . -1.5(5) ?
F34 C34 C35 F35 . . . . -1.9(5) ?
C33 C34 C35 F35 . . . . 178.8(3) ?
F34 C34 C35 C36 . . . . 179.0(3) ?
C33 C34 C35 C36 . . . . -0.3(5) ?
F35 C35 C36 F36 . . . . 2.9(4) ?
C34 C35 C36 F36 . . . . -178.1(3) ?
F35 C35 C36 C31 . . . . -177.1(3) ?
C34 C35 C36 C31 . . . . 1.9(5) ?
C32 C31 C36 F36 . . . . 178.4(2) ?
B1 C31 C36 F36 . . . . -2.8(4) ?
C32 C31 C36 C35 . . . . -1.6(4) ?
B1 C31 C36 C35 . . . . 177.2(3) ?
O1 N3 C41 C42 . . . . 163.7(2) ?
C17 N3 C41 C42 . . . . 55.5(3) ?
O1 N3 C41 C46 . . . . -21.2(4) ?
C17 N3 C41 C46 . . . . -129.4(3) ?
C46 C41 C42 C43 . . . . 0.1(5) ?
N3 C41 C42 C43 . . . . 175.2(3) ?
C41 C42 C43 C44 . . . . -0.4(5) ?
C42 C43 C44 C45 . . . . 0.2(6) ?
C43 C44 C45 C46 . . . . 0.3(7) ?
C42 C41 C46 C45 . . . . 0.4(5) ?
N3 C41 C46 C45 . . . . -174.7(3) ?
C44 C45 C46 C41 . . . . -0.7(6) ?


####################################################################### 
# 
# 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_erk10356
_database_code_depnum_ccdc_archive 'CCDC 2182533'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2022-06-28 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;

_audit_creation_method           'APEX4 v2021.4-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H43 B F5 N3 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         651.55

_chemical_melting_point          ?

_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                   9.2846(4)
_cell_length_b                   10.7049(5)
_cell_length_c                   19.0761(8)
_cell_angle_alpha                94.642(2)
_cell_angle_beta                 99.478(2)
_cell_angle_gamma                93.573(2)
_cell_volume                     1858.44(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4736
_cell_measurement_theta_min      2.2305
_cell_measurement_theta_max      25.9700
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.084
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688

_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Mo ImS'
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          'single crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            48227
_diffrn_reflns_av_R_equivalents  0.0963
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_refine_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.

A badly disordered half heptane molecule was found in the 
asymmetrical unit and could not be satisfactorily refined. The program 
SQUEEZE (Spek, A.L. (2015). Acta Cryst. C71, 9-18) was therefore used to
remove mathematically the effect of the solvent.
The quoted formula and derived parameters are not included the squeezed
solvent molecule. 
;

_reflns_number_total             6791
_reflns_number_gt                4794
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1294
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_number_reflns         6791
_refine_ls_number_parameters     434
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0537P)²+0.7797P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
N N 0.0061 0.0033 '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'

_computing_data_collection       'Bruker APEX4 v2021.4-0 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1242)'
_computing_publication_material  'SHELXT 2018/2 (Sheldrick, 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.4874(3) 0.6465(2) 0.74511(12) 0.0227(5) Uani d . . . 1 . .
N N1 0.23913(18) 0.72687(15) 0.77588(9) 0.0220(4) Uani d . . . 1 . .
N N2 0.21843(18) 0.65270(15) 0.66600(9) 0.0213(4) Uani d . . . 1 . .
N N3 0.52755(19) 0.45826(15) 0.76710(9) 0.0246(4) Uani d . . . 1 . .
O O1 0.51829(16) 0.53051(13) 0.70274(7) 0.0251(3) Uani d . . . 1 . .
C C1 0.3168(2) 0.68043(18) 0.72679(10) 0.0219(4) Uani d . . . 1 . .
C C2 0.0915(2) 0.72434(19) 0.74600(11) 0.0254(5) Uani d . . . 1 . .
H H2 0.014317 0.749754 0.769640 0.030000 Uiso calc U . R 1 . .
C C3 0.0793(2) 0.67910(19) 0.67736(11) 0.0249(5) Uani d . . . 1 . .
H H3 -0.008154 0.667387 0.643061 0.030000 Uiso calc U . R 1 . .
C C4 0.6699(2) 0.4001(2) 0.77758(12) 0.0287(5) Uani d . . . 1 . .
C C5 0.6830(3) 0.3486(2) 0.85082(12) 0.0365(6) Uani d . . . 1 . .
H H5A 0.696310 0.418729 0.888205 0.055000 Uiso calc U . R 1 . .
H H5B 0.767474 0.297681 0.857904 0.055000 Uiso calc U . R 1 . .
H H5C 0.593691 0.296434 0.853200 0.055000 Uiso calc U . R 1 . .
C C6 0.6578(3) 0.2920(2) 0.71913(12) 0.0359(5) Uani d . . . 1 . .
H H6A 0.578184 0.230491 0.723966 0.054000 Uiso calc U . R 1 . .
H H6B 0.750235 0.251383 0.723615 0.054000 Uiso calc U . R 1 . .
H H6C 0.637390 0.324654 0.672272 0.054000 Uiso calc U . R 1 . .
C C7 0.8021(2) 0.4897(2) 0.77346(13) 0.0345(5) Uani d . . . 1 . .
H H7A 0.792013 0.519422 0.725757 0.052000 Uiso calc U . R 1 . .
H H7B 0.891674 0.445626 0.782750 0.052000 Uiso calc U . R 1 . .
H H7C 0.807358 0.561671 0.809230 0.052000 Uiso calc U . R 1 . .
C C11 0.2961(2) 0.76640(19) 0.85053(11) 0.0242(4) Uani d . . . 1 . .
C C12 0.3618(2) 0.6784(2) 0.89351(11) 0.0259(5) Uani d . . . 1 . .
C C13 0.4080(2) 0.7174(2) 0.96561(11) 0.0312(5) Uani d . . . 1 . .
H H13 0.453740 0.660401 0.996264 0.037000 Uiso calc U . R 1 . .
C C14 0.3887(3) 0.8369(2) 0.99342(12) 0.0338(5) Uani d . . . 1 . .
H H14 0.416764 0.860241 1.043160 0.041000 Uiso calc U . R 1 . .
C C15 0.3284(2) 0.9231(2) 0.94890(12) 0.0319(5) Uani d . . . 1 . .
H H15 0.318663 1.006015 0.968440 0.038000 Uiso calc U . R 1 . .
C C16 0.2816(2) 0.8908(2) 0.87605(11) 0.0265(5) Uani d . . . 1 . .
C C17 0.3955(2) 0.55002(19) 0.86353(11) 0.0264(5) Uani d . . . 1 . .
H H17 0.442386 0.507193 0.905149 0.032000 Uiso calc U . R 1 . .
C C18 0.5141(2) 0.57090(18) 0.81674(11) 0.0238(4) Uani d . . . 1 . .
H H18 0.610881 0.599615 0.846975 0.029000 Uiso calc U . R 1 . .
C C19 0.2606(3) 0.4637(2) 0.82749(13) 0.0331(5) Uani d . . . 1 . .
H H19A 0.190824 0.456823 0.860613 0.050000 Uiso calc U . R 1 . .
H H19B 0.290988 0.380160 0.814467 0.050000 Uiso calc U . R 1 . .
H H19C 0.213935 0.499211 0.784433 0.050000 Uiso calc U . R 1 . .
C C20 0.2274(2) 0.9898(2) 0.82667(12) 0.0298(5) Uani d . . . 1 . .
H H20 0.142117 0.949659 0.791390 0.036000 Uiso calc U . R 1 . .
C C21 0.1761(3) 1.1052(2) 0.86503(13) 0.0374(6) Uani d . . . 1 . .
H H21A 0.260142 1.152026 0.896010 0.056000 Uiso calc U . R 1 . .
H H21B 0.103848 1.078475 0.893951 0.056000 Uiso calc U . R 1 . .
H H21C 0.131491 1.159226 0.829733 0.056000 Uiso calc U . R 1 . .
C C22 0.3469(3) 1.0308(2) 0.78488(12) 0.0364(6) Uani d . . . 1 . .
H H22A 0.309309 1.091018 0.751675 0.055000 Uiso calc U . R 1 . .
H H22B 0.375499 0.957095 0.758027 0.055000 Uiso calc U . R 1 . .
H H22C 0.432229 1.070375 0.818187 0.055000 Uiso calc U . R 1 . .
C C31 0.2525(2) 0.61588(19) 0.59572(10) 0.0230(4) Uani d . . . 1 . .
C C32 0.2511(2) 0.48794(19) 0.57323(11) 0.0252(5) Uani d . . . 1 . .
C C33 0.2845(2) 0.4587(2) 0.50557(11) 0.0299(5) Uani d . . . 1 . .
H H33 0.284687 0.372984 0.488234 0.036000 Uiso calc U . R 1 . .
C C34 0.3175(3) 0.5516(2) 0.46290(12) 0.0322(5) Uani d . . . 1 . .
H H34 0.341791 0.529223 0.417313 0.039000 Uiso calc U . R 1 . .
C C35 0.3151(2) 0.6771(2) 0.48658(11) 0.0307(5) Uani d . . . 1 . .
H H35 0.336195 0.740067 0.456634 0.037000 Uiso calc U . R 1 . .
C C36 0.2821(2) 0.71213(19) 0.55371(11) 0.0249(5) Uani d . . . 1 . .
C C37 0.2165(2) 0.38603(19) 0.62034(12) 0.0294(5) Uani d . . . 1 . .
H H37 0.258168 0.417422 0.670853 0.035000 Uiso calc U . R 1 . .
C C38 0.0515(3) 0.3594(2) 0.61554(16) 0.0459(6) Uani d . . . 1 . .
H H38A 0.006838 0.332830 0.565945 0.069000 Uiso calc U . R 1 . .
H H38B 0.009027 0.435830 0.631848 0.069000 Uiso calc U . R 1 . .
H H38C 0.032600 0.292503 0.645759 0.069000 Uiso calc U . R 1 . .
C C39 0.2846(3) 0.2639(2) 0.60299(13) 0.0383(6) Uani d . . . 1 . .
H H39A 0.235747 0.224773 0.556181 0.057000 Uiso calc U . R 1 . .
H H39B 0.272790 0.206456 0.639489 0.057000 Uiso calc U . R 1 . .
H H39C 0.389069 0.281753 0.602129 0.057000 Uiso calc U . R 1 . .
C C40 0.2757(2) 0.85035(19) 0.57833(12) 0.0284(5) Uani d . . . 1 . .
H H40 0.287699 0.858628 0.631608 0.034000 Uiso calc U . R 1 . .
C C41 0.1273(3) 0.8967(2) 0.54905(15) 0.0404(6) Uani d . . . 1 . .
H H41A 0.115290 0.894166 0.496932 0.061000 Uiso calc U . R 1 . .
H H41B 0.122296 0.983212 0.569152 0.061000 Uiso calc U . R 1 . .
H H41C 0.048987 0.842475 0.562280 0.061000 Uiso calc U . R 1 . .
C C42 0.3974(2) 0.9351(2) 0.55712(14) 0.0357(5) Uani d . . . 1 . .
H H42A 0.378624 0.939692 0.505350 0.054000 Uiso calc U . R 1 . .
H H42B 0.491923 0.900158 0.570991 0.054000 Uiso calc U . R 1 . .
H H42C 0.399508 1.019544 0.581442 0.054000 Uiso calc U . R 1 . .
C C51 0.6012(2) 0.76708(18) 0.73906(11) 0.0227(4) Uani d . . . 1 . .
C C52 0.6569(2) 0.85883(19) 0.79435(11) 0.0250(5) Uani d . . . 1 . .
C C53 0.7582(2) 0.95666(19) 0.78884(12) 0.0292(5) Uani d . . . 1 . .
C C54 0.8097(2) 0.96531(19) 0.72553(13) 0.0300(5) Uani d . . . 1 . .
C C55 0.7579(2) 0.8781(2) 0.66908(12) 0.0291(5) Uani d . . . 1 . .
C C56 0.6567(2) 0.78185(19) 0.67675(11) 0.0244(4) Uani d . . . 1 . .
F F52 0.61060(13) 0.85709(11) 0.85772(6) 0.0302(3) Uani d . . . 1 . .
F F53 0.80569(14) 1.04298(12) 0.84468(7) 0.0393(3) Uani d . . . 1 . .
F F54 0.90906(14) 1.05918(12) 0.71884(8) 0.0414(4) Uani d . . . 1 . .
F F55 0.80552(15) 0.88646(13) 0.60617(7) 0.0410(3) Uani d . . . 1 . .
F F56 0.60927(14) 0.70070(11) 0.61842(6) 0.0316(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 O1 . 1.495(3) ?
B1 C1 . 1.635(3) ?
B1 C18 . 1.636(3) ?
B1 C51 . 1.641(3) ?
N1 C1 . 1.355(3) ?
N1 C2 . 1.392(3) ?
N1 C11 . 1.454(3) ?
N2 C1 . 1.352(3) ?
N2 C3 . 1.387(3) ?
N2 C31 . 1.457(3) ?
N3 C4 . 1.486(3) ?
N3 C18 . 1.496(3) ?
N3 O1 . 1.497(2) ?
C2 C3 . 1.343(3) ?
C2 H2 . 0.950000 ?
C3 H3 . 0.950000 ?
C4 C6 . 1.526(3) ?
C4 C7 . 1.527(3) ?
C4 C5 . 1.532(3) ?
C5 H5A . 0.980000 ?
C5 H5B . 0.980000 ?
C5 H5C . 0.980000 ?
C6 H6A . 0.980000 ?
C6 H6B . 0.980000 ?
C6 H6C . 0.980000 ?
C7 H7A . 0.980000 ?
C7 H7B . 0.980000 ?
C7 H7C . 0.980000 ?
C11 C12 . 1.401(3) ?
C11 C16 . 1.402(3) ?
C12 C13 . 1.393(3) ?
C12 C17 . 1.516(3) ?
C13 C14 . 1.379(3) ?
C13 H13 . 0.950000 ?
C14 C15 . 1.386(3) ?
C14 H14 . 0.950000 ?
C15 C16 . 1.394(3) ?
C15 H15 . 0.950000 ?
C16 C20 . 1.528(3) ?
C17 C19 . 1.538(3) ?
C17 C18 . 1.545(3) ?
C17 H17 . 1.000000 ?
C18 H18 . 1.000000 ?
C19 H19A . 0.980000 ?
C19 H19B . 0.980000 ?
C19 H19C . 0.980000 ?
C20 C21 . 1.527(3) ?
C20 C22 . 1.531(3) ?
C20 H20 . 1.000000 ?
C21 H21A . 0.980000 ?
C21 H21B . 0.980000 ?
C21 H21C . 0.980000 ?
C22 H22A . 0.980000 ?
C22 H22B . 0.980000 ?
C22 H22C . 0.980000 ?
C31 C36 . 1.397(3) ?
C31 C32 . 1.400(3) ?
C32 C33 . 1.392(3) ?
C32 C37 . 1.520(3) ?
C33 C34 . 1.386(3) ?
C33 H33 . 0.950000 ?
C34 C35 . 1.384(3) ?
C34 H34 . 0.950000 ?
C35 C36 . 1.393(3) ?
C35 H35 . 0.950000 ?
C36 C40 . 1.524(3) ?
C37 C39 . 1.524(3) ?
C37 C38 . 1.527(3) ?
C37 H37 . 1.000000 ?
C38 H38A . 0.980000 ?
C38 H38B . 0.980000 ?
C38 H38C . 0.980000 ?
C39 H39A . 0.980000 ?
C39 H39B . 0.980000 ?
C39 H39C . 0.980000 ?
C40 C41 . 1.528(3) ?
C40 C42 . 1.532(3) ?
C40 H40 . 1.000000 ?
C41 H41A . 0.980000 ?
C41 H41B . 0.980000 ?
C41 H41C . 0.980000 ?
C42 H42A . 0.980000 ?
C42 H42B . 0.980000 ?
C42 H42C . 0.980000 ?
C51 C56 . 1.387(3) ?
C51 C52 . 1.391(3) ?
C52 F52 . 1.349(2) ?
C52 C53 . 1.385(3) ?
C53 F53 . 1.348(2) ?
C53 C54 . 1.378(3) ?
C54 F54 . 1.350(2) ?
C54 C55 . 1.369(3) ?
C55 F55 . 1.353(2) ?
C55 C56 . 1.384(3) ?
C56 F56 . 1.349(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 B1 C1 . . 113.09(17) ?
O1 B1 C18 . . 88.66(14) ?
C1 B1 C18 . . 110.66(17) ?
O1 B1 C51 . . 112.23(17) ?
C1 B1 C51 . . 111.66(16) ?
C18 B1 C51 . . 118.72(17) ?
C1 N1 C2 . . 110.17(17) ?
C1 N1 C11 . . 126.20(17) ?
C2 N1 C11 . . 123.51(17) ?
C1 N2 C3 . . 110.40(17) ?
C1 N2 C31 . . 125.94(17) ?
C3 N2 C31 . . 123.21(16) ?
C4 N3 C18 . . 116.84(16) ?
C4 N3 O1 . . 108.67(15) ?
C18 N3 O1 . . 94.05(13) ?
B1 O1 N3 . . 90.99(13) ?
N2 C1 N1 . . 105.46(17) ?
N2 C1 B1 . . 129.47(18) ?
N1 C1 B1 . . 124.36(17) ?
C3 C2 N1 . . 106.85(18) ?
C3 C2 H2 . . 126.600000 ?
N1 C2 H2 . . 126.600000 ?
C2 C3 N2 . . 107.08(18) ?
C2 C3 H3 . . 126.500000 ?
N2 C3 H3 . . 126.500000 ?
N3 C4 C6 . . 106.66(18) ?
N3 C4 C7 . . 114.30(17) ?
C6 C4 C7 . . 109.08(19) ?
N3 C4 C5 . . 105.41(17) ?
C6 C4 C5 . . 110.00(18) ?
C7 C4 C5 . . 111.22(19) ?
C4 C5 H5A . . 109.500000 ?
C4 C5 H5B . . 109.500000 ?
H5A C5 H5B . . 109.500000 ?
C4 C5 H5C . . 109.500000 ?
H5A C5 H5C . . 109.500000 ?
H5B C5 H5C . . 109.500000 ?
C4 C6 H6A . . 109.500000 ?
C4 C6 H6B . . 109.500000 ?
H6A C6 H6B . . 109.500000 ?
C4 C6 H6C . . 109.500000 ?
H6A C6 H6C . . 109.500000 ?
H6B C6 H6C . . 109.500000 ?
C4 C7 H7A . . 109.500000 ?
C4 C7 H7B . . 109.500000 ?
H7A C7 H7B . . 109.500000 ?
C4 C7 H7C . . 109.500000 ?
H7A C7 H7C . . 109.500000 ?
H7B C7 H7C . . 109.500000 ?
C12 C11 C16 . . 123.25(19) ?
C12 C11 N1 . . 118.53(18) ?
C16 C11 N1 . . 118.22(18) ?
C13 C12 C11 . . 117.0(2) ?
C13 C12 C17 . . 119.99(19) ?
C11 C12 C17 . . 122.76(18) ?
C14 C13 C12 . . 121.4(2) ?
C14 C13 H13 . . 119.300000 ?
C12 C13 H13 . . 119.300000 ?
C13 C14 C15 . . 120.1(2) ?
C13 C14 H14 . . 120.000000 ?
C15 C14 H14 . . 120.000000 ?
C14 C15 C16 . . 121.4(2) ?
C14 C15 H15 . . 119.300000 ?
C16 C15 H15 . . 119.300000 ?
C15 C16 C11 . . 116.69(19) ?
C15 C16 C20 . . 120.72(19) ?
C11 C16 C20 . . 122.46(18) ?
C12 C17 C19 . . 114.86(18) ?
C12 C17 C18 . . 107.35(16) ?
C19 C17 C18 . . 115.05(18) ?
C12 C17 H17 . . 106.300000 ?
C19 C17 H17 . . 106.300000 ?
C18 C17 H17 . . 106.300000 ?
N3 C18 C17 . . 113.29(16) ?
N3 C18 B1 . . 85.77(14) ?
C17 C18 B1 . . 122.81(17) ?
N3 C18 H18 . . 110.800000 ?
C17 C18 H18 . . 110.800000 ?
B1 C18 H18 . . 110.800000 ?
C17 C19 H19A . . 109.500000 ?
C17 C19 H19B . . 109.500000 ?
H19A C19 H19B . . 109.500000 ?
C17 C19 H19C . . 109.500000 ?
H19A C19 H19C . . 109.500000 ?
H19B C19 H19C . . 109.500000 ?
C21 C20 C16 . . 113.99(19) ?
C21 C20 C22 . . 109.59(19) ?
C16 C20 C22 . . 110.14(18) ?
C21 C20 H20 . . 107.600000 ?
C16 C20 H20 . . 107.600000 ?
C22 C20 H20 . . 107.600000 ?
C20 C21 H21A . . 109.500000 ?
C20 C21 H21B . . 109.500000 ?
H21A C21 H21B . . 109.500000 ?
C20 C21 H21C . . 109.500000 ?
H21A C21 H21C . . 109.500000 ?
H21B C21 H21C . . 109.500000 ?
C20 C22 H22A . . 109.500000 ?
C20 C22 H22B . . 109.500000 ?
H22A C22 H22B . . 109.500000 ?
C20 C22 H22C . . 109.500000 ?
H22A C22 H22C . . 109.500000 ?
H22B C22 H22C . . 109.500000 ?
C36 C31 C32 . . 123.58(19) ?
C36 C31 N2 . . 117.22(17) ?
C32 C31 N2 . . 119.19(17) ?
C33 C32 C31 . . 116.50(19) ?
C33 C32 C37 . . 121.58(19) ?
C31 C32 C37 . . 121.91(18) ?
C34 C33 C32 . . 121.6(2) ?
C34 C33 H33 . . 119.200000 ?
C32 C33 H33 . . 119.200000 ?
C35 C34 C33 . . 120.1(2) ?
C35 C34 H34 . . 119.900000 ?
C33 C34 H34 . . 119.900000 ?
C34 C35 C36 . . 120.9(2) ?
C34 C35 H35 . . 119.600000 ?
C36 C35 H35 . . 119.500000 ?
C35 C36 C31 . . 117.27(19) ?
C35 C36 C40 . . 120.39(18) ?
C31 C36 C40 . . 122.32(18) ?
C32 C37 C39 . . 112.80(19) ?
C32 C37 C38 . . 111.36(19) ?
C39 C37 C38 . . 109.35(19) ?
C32 C37 H37 . . 107.700000 ?
C39 C37 H37 . . 107.700000 ?
C38 C37 H37 . . 107.700000 ?
C37 C38 H38A . . 109.500000 ?
C37 C38 H38B . . 109.500000 ?
H38A C38 H38B . . 109.500000 ?
C37 C38 H38C . . 109.500000 ?
H38A C38 H38C . . 109.500000 ?
H38B C38 H38C . . 109.500000 ?
C37 C39 H39A . . 109.500000 ?
C37 C39 H39B . . 109.500000 ?
H39A C39 H39B . . 109.500000 ?
C37 C39 H39C . . 109.500000 ?
H39A C39 H39C . . 109.500000 ?
H39B C39 H39C . . 109.500000 ?
C36 C40 C41 . . 110.95(18) ?
C36 C40 C42 . . 112.85(18) ?
C41 C40 C42 . . 109.19(18) ?
C36 C40 H40 . . 107.900000 ?
C41 C40 H40 . . 107.900000 ?
C42 C40 H40 . . 107.900000 ?
C40 C41 H41A . . 109.500000 ?
C40 C41 H41B . . 109.500000 ?
H41A C41 H41B . . 109.500000 ?
C40 C41 H41C . . 109.500000 ?
H41A C41 H41C . . 109.500000 ?
H41B C41 H41C . . 109.500000 ?
C40 C42 H42A . . 109.500000 ?
C40 C42 H42B . . 109.500000 ?
H42A C42 H42B . . 109.500000 ?
C40 C42 H42C . . 109.500000 ?
H42A C42 H42C . . 109.500000 ?
H42B C42 H42C . . 109.500000 ?
C56 C51 C52 . . 113.73(19) ?
C56 C51 B1 . . 121.10(18) ?
C52 C51 B1 . . 125.09(18) ?
F52 C52 C53 . . 115.98(19) ?
F52 C52 C51 . . 120.01(18) ?
C53 C52 C51 . . 124.0(2) ?
F53 C53 C54 . . 120.17(19) ?
F53 C53 C52 . . 120.5(2) ?
C54 C53 C52 . . 119.3(2) ?
F54 C54 C55 . . 120.2(2) ?
F54 C54 C53 . . 120.6(2) ?
C55 C54 C53 . . 119.23(19) ?
F55 C55 C54 . . 119.96(19) ?
F55 C55 C56 . . 120.4(2) ?
C54 C55 C56 . . 119.6(2) ?
F56 C56 C55 . . 116.12(18) ?
F56 C56 C51 . . 119.79(18) ?
C55 C56 C51 . . 124.1(2) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 B1 O1 N3 . . . . -106.55(17) ?
C18 B1 O1 N3 . . . . 5.39(14) ?
C51 B1 O1 N3 . . . . 126.03(16) ?
C4 N3 O1 B1 . . . . -126.02(16) ?
C18 N3 O1 B1 . . . . -5.91(15) ?
C3 N2 C1 N1 . . . . -1.3(2) ?
C31 N2 C1 N1 . . . . 171.25(17) ?
C3 N2 C1 B1 . . . . 169.21(19) ?
C31 N2 C1 B1 . . . . -18.3(3) ?
C2 N1 C1 N2 . . . . 1.8(2) ?
C11 N1 C1 N2 . . . . 177.89(17) ?
C2 N1 C1 B1 . . . . -169.31(18) ?
C11 N1 C1 B1 . . . . 6.8(3) ?
O1 B1 C1 N2 . . . . -26.9(3) ?
C18 B1 C1 N2 . . . . -124.6(2) ?
C51 B1 C1 N2 . . . . 100.8(2) ?
O1 B1 C1 N1 . . . . 141.95(18) ?
C18 B1 C1 N1 . . . . 44.3(3) ?
C51 B1 C1 N1 . . . . -90.3(2) ?
C1 N1 C2 C3 . . . . -1.7(2) ?
C11 N1 C2 C3 . . . . -177.89(17) ?
N1 C2 C3 N2 . . . . 0.8(2) ?
C1 N2 C3 C2 . . . . 0.3(2) ?
C31 N2 C3 C2 . . . . -172.49(17) ?
C18 N3 C4 C6 . . . . -177.66(17) ?
O1 N3 C4 C6 . . . . -72.91(19) ?
C18 N3 C4 C7 . . . . -57.0(2) ?
O1 N3 C4 C7 . . . . 47.7(2) ?
C18 N3 C4 C5 . . . . 65.4(2) ?
O1 N3 C4 C5 . . . . 170.15(16) ?
C1 N1 C11 C12 . . . . -58.9(3) ?
C2 N1 C11 C12 . . . . 116.7(2) ?
C1 N1 C11 C16 . . . . 121.5(2) ?
C2 N1 C11 C16 . . . . -62.9(3) ?
C16 C11 C12 C13 . . . . 3.0(3) ?
N1 C11 C12 C13 . . . . -176.57(18) ?
C16 C11 C12 C17 . . . . -171.5(2) ?
N1 C11 C12 C17 . . . . 9.0(3) ?
C11 C12 C13 C14 . . . . 0.5(3) ?
C17 C12 C13 C14 . . . . 175.1(2) ?
C12 C13 C14 C15 . . . . -3.0(3) ?
C13 C14 C15 C16 . . . . 2.1(3) ?
C14 C15 C16 C11 . . . . 1.2(3) ?
C14 C15 C16 C20 . . . . -174.8(2) ?
C12 C11 C16 C15 . . . . -3.8(3) ?
N1 C11 C16 C15 . . . . 175.74(18) ?
C12 C11 C16 C20 . . . . 172.1(2) ?
N1 C11 C16 C20 . . . . -8.3(3) ?
C13 C12 C17 C19 . . . . 122.4(2) ?
C11 C12 C17 C19 . . . . -63.3(3) ?
C13 C12 C17 C18 . . . . -108.3(2) ?
C11 C12 C17 C18 . . . . 66.0(3) ?
C4 N3 C18 C17 . . . . -117.26(19) ?
O1 N3 C18 C17 . . . . 129.45(16) ?
C4 N3 C18 B1 . . . . 118.71(17) ?
O1 N3 C18 B1 . . . . 5.41(14) ?
C12 C17 C18 N3 . . . . -163.16(16) ?
C19 C17 C18 N3 . . . . -33.9(2) ?
C12 C17 C18 B1 . . . . -62.7(2) ?
C19 C17 C18 B1 . . . . 66.5(2) ?
O1 B1 C18 N3 . . . . -5.41(14) ?
C1 B1 C18 N3 . . . . 108.82(17) ?
C51 B1 C18 N3 . . . . -120.16(19) ?
O1 B1 C18 C17 . . . . -120.50(19) ?
C1 B1 C18 C17 . . . . -6.3(3) ?
C51 B1 C18 C17 . . . . 124.8(2) ?
C15 C16 C20 C21 . . . . -21.6(3) ?
C11 C16 C20 C21 . . . . 162.6(2) ?
C15 C16 C20 C22 . . . . 102.0(2) ?
C11 C16 C20 C22 . . . . -73.7(3) ?
C1 N2 C31 C36 . . . . -87.4(2) ?
C3 N2 C31 C36 . . . . 84.2(2) ?
C1 N2 C31 C32 . . . . 93.9(2) ?
C3 N2 C31 C32 . . . . -94.5(2) ?
C36 C31 C32 C33 . . . . 1.4(3) ?
N2 C31 C32 C33 . . . . 179.99(18) ?
C36 C31 C32 C37 . . . . -179.2(2) ?
N2 C31 C32 C37 . . . . -0.6(3) ?
C31 C32 C33 C34 . . . . 0.1(3) ?
C37 C32 C33 C34 . . . . -179.3(2) ?
C32 C33 C34 C35 . . . . -1.2(3) ?
C33 C34 C35 C36 . . . . 1.1(3) ?
C34 C35 C36 C31 . . . . 0.3(3) ?
C34 C35 C36 C40 . . . . -178.3(2) ?
C32 C31 C36 C35 . . . . -1.5(3) ?
N2 C31 C36 C35 . . . . 179.82(18) ?
C32 C31 C36 C40 . . . . 177.0(2) ?
N2 C31 C36 C40 . . . . -1.6(3) ?
C33 C32 C37 C39 . . . . 25.2(3) ?
C31 C32 C37 C39 . . . . -154.1(2) ?
C33 C32 C37 C38 . . . . -98.2(2) ?
C31 C32 C37 C38 . . . . 82.5(3) ?
C35 C36 C40 C41 . . . . 82.5(3) ?
C31 C36 C40 C41 . . . . -95.9(2) ?
C35 C36 C40 C42 . . . . -40.4(3) ?
C31 C36 C40 C42 . . . . 141.2(2) ?
O1 B1 C51 C56 . . . . 33.5(3) ?
C1 B1 C51 C56 . . . . -94.7(2) ?
C18 B1 C51 C56 . . . . 134.8(2) ?
O1 B1 C51 C52 . . . . -143.11(19) ?
C1 B1 C51 C52 . . . . 88.7(2) ?
C18 B1 C51 C52 . . . . -41.9(3) ?
C56 C51 C52 F52 . . . . 178.90(17) ?
B1 C51 C52 F52 . . . . -4.3(3) ?
C56 C51 C52 C53 . . . . 0.1(3) ?
B1 C51 C52 C53 . . . . 176.92(19) ?
F52 C52 C53 F53 . . . . 0.3(3) ?
C51 C52 C53 F53 . . . . 179.18(18) ?
F52 C52 C53 C54 . . . . -179.45(17) ?
C51 C52 C53 C54 . . . . -0.6(3) ?
F53 C53 C54 F54 . . . . 0.7(3) ?
C52 C53 C54 F54 . . . . -179.56(18) ?
F53 C53 C54 C55 . . . . -178.78(18) ?
C52 C53 C54 C55 . . . . 1.0(3) ?
F54 C54 C55 F55 . . . . -0.6(3) ?
C53 C54 C55 F55 . . . . 178.87(18) ?
F54 C54 C55 C56 . . . . 179.65(18) ?
C53 C54 C55 C56 . . . . -0.9(3) ?
F55 C55 C56 F56 . . . . -0.7(3) ?
C54 C55 C56 F56 . . . . 179.04(18) ?
F55 C55 C56 C51 . . . . -179.37(18) ?
C54 C55 C56 C51 . . . . 0.4(3) ?
C52 C51 C56 F56 . . . . -178.57(17) ?
B1 C51 C56 F56 . . . . 4.5(3) ?
C52 C51 C56 C55 . . . . 0.0(3) ?
B1 C51 C56 C55 . . . . -176.97(19) ?




#=============================================================================
#  end of cif data for "erk10356" (compound 4c)
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================
####################################################################### 
# 
# 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_4_erk10081
_database_code_depnum_ccdc_archive 'CCDC 2157862'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2022-03-11 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2019.11-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H39 B F5 N3 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         671.54

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.5222(3)
_cell_length_b                   18.1892(5)
_cell_length_c                   19.3469(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.624(2)
_cell_angle_gamma                90
_cell_volume                     3340.00(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5140
_cell_measurement_theta_min      4.5860
_cell_measurement_theta_max      66.5426
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408

_exptl_absorpt_coefficient_mu    0.825
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption
correction. Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M.
& Stalke D., J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu sealed tube'
_diffrn_source_type              'fine-focus sealed tube'
_diffrn_source_power             1.50
_diffrn_source_current           30.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device       'Bruker APEXII Diffractometer'
_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            44910
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_theta_min         4.59
_diffrn_reflns_theta_max         66.70
_diffrn_reflns_theta_full        66.70
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23

_refine_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_number_total             5909
_reflns_number_gt                4460
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1064
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_number_reflns         5909
_refine_ls_number_parameters     449
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0524P)²+0.5608P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.258
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
N N 0.0311 0.0180 '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'

_computing_data_collection       'Bruker APEX3 v2019.11-0 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.2854(2) 0.45701(11) 0.70811(10) 0.0165(4) Uani d . . . 1 . .
N N1 0.33122(16) 0.58378(8) 0.65183(8) 0.0171(3) Uani d . . . 1 . .
N N2 0.43814(16) 0.57659(8) 0.75380(7) 0.0166(3) Uani d . . . 1 . .
N N3 0.18893(16) 0.38970(8) 0.62858(7) 0.0166(3) Uani d . . . 1 . .
O O1 0.13921(13) 0.44986(6) 0.67205(6) 0.0163(3) Uani d . . . 1 . .
C C1 0.34798(19) 0.53974(9) 0.70822(9) 0.0156(4) Uani d . . . 1 . .
C C2 0.4100(2) 0.64734(10) 0.66199(10) 0.0202(4) Uani d . . . 1 . .
H H2 0.415887 0.686581 0.629946 0.024 Uiso calc U . R 1 . .
C C3 0.4765(2) 0.64307(10) 0.72552(10) 0.0207(4) Uani d . . . 1 . .
H H3 0.538194 0.67877 0.747154 0.025 Uiso calc U . R 1 . .
C C11 0.25242(19) 0.56691(9) 0.58637(9) 0.0170(4) Uani d . . . 1 . .
C C12 0.29031(19) 0.50418(10) 0.55054(9) 0.0169(4) Uani d . . . 1 . .
C C13 0.2221(2) 0.49358(10) 0.48491(9) 0.0201(4) Uani d . . . 1 . .
H H13 0.244305 0.451599 0.45869 0.024 Uiso calc U . R 1 . .
C C14 0.1221(2) 0.54319(11) 0.45704(9) 0.0222(4) Uani d . . . 1 . .
H H14 0.078732 0.535549 0.411643 0.027 Uiso calc U . R 1 . .
C C15 0.0852(2) 0.60364(10) 0.49497(9) 0.0205(4) Uani d . . . 1 . .
H H15 0.015859 0.636844 0.475498 0.025 Uiso calc U . R 1 . .
C C16 0.14853(19) 0.61654(10) 0.56156(9) 0.0186(4) Uani d . . . 1 . .
C C17 0.39806(19) 0.44937(10) 0.58285(9) 0.0175(4) Uani d . . . 1 . .
H H17 0.482626 0.4781 0.601069 0.021 Uiso calc U . R 1 . .
C C18 0.34186(19) 0.40821(10) 0.64495(9) 0.0169(4) Uani d . . . 1 . .
H H18 0.400939 0.365142 0.661148 0.02 Uiso calc U . R 1 . .
C C19 0.4470(2) 0.39399(10) 0.53034(10) 0.0228(4) Uani d . . . 1 . .
H H19A 0.369768 0.360108 0.516507 0.034 Uiso calc U . R 1 . .
H H19B 0.527494 0.366146 0.551449 0.034 Uiso calc U . R 1 . .
H H19C 0.47507 0.420235 0.489412 0.034 Uiso calc U . R 1 . .
C C20 0.0962(2) 0.67966(10) 0.60410(10) 0.0216(4) Uani d . . . 1 . .
H H20 0.148065 0.677779 0.65111 0.026 Uiso calc U . R 1 . .
C C21 -0.0613(2) 0.67082(11) 0.61331(10) 0.0268(4) Uani d . . . 1 . .
H H21A -0.115086 0.675252 0.568133 0.04 Uiso calc U . R 1 . .
H H21B -0.091323 0.709173 0.644504 0.04 Uiso calc U . R 1 . .
H H21C -0.078246 0.622365 0.633181 0.04 Uiso calc U . R 1 . .
C C22 0.1254(2) 0.75447(11) 0.57198(11) 0.0302(5) Uani d . . . 1 . .
H H22A 0.226882 0.760039 0.568368 0.045 Uiso calc U . R 1 . .
H H22B 0.092071 0.793655 0.601352 0.045 Uiso calc U . R 1 . .
H H22C 0.075851 0.757616 0.525669 0.045 Uiso calc U . R 1 . .
C C31 0.49976(19) 0.55426(9) 0.82168(9) 0.0164(4) Uani d . . . 1 . .
C C32 0.61154(19) 0.50373(10) 0.82528(9) 0.0177(4) Uani d . . . 1 . .
C C33 0.6808(2) 0.49122(10) 0.89050(10) 0.0211(4) Uani d . . . 1 . .
H H33 0.755802 0.456671 0.895367 0.025 Uiso calc U . R 1 . .
C C34 0.6416(2) 0.52862(11) 0.94825(9) 0.0232(4) Uani d . . . 1 . .
H H34 0.691998 0.520503 0.991973 0.028 Uiso calc U . R 1 . .
C C35 0.5304(2) 0.57743(10) 0.94328(10) 0.0222(4) Uani d . . . 1 . .
H H35 0.504784 0.601997 0.983724 0.027 Uiso calc U . R 1 . .
C C36 0.4549(2) 0.59133(10) 0.87958(9) 0.0188(4) Uani d . . . 1 . .
C C37 0.6572(2) 0.46482(10) 0.76129(10) 0.0216(4) Uani d . . . 1 . .
H H37 0.57013 0.452242 0.731219 0.026 Uiso calc U . R 1 . .
C C38 0.7478(2) 0.51488(12) 0.71918(11) 0.0310(5) Uani d . . . 1 . .
H H38A 0.695247 0.559767 0.70617 0.046 Uiso calc U . R 1 . .
H H38B 0.771587 0.489083 0.677206 0.046 Uiso calc U . R 1 . .
H H38C 0.834602 0.527782 0.747255 0.046 Uiso calc U . R 1 . .
C C39 0.7371(2) 0.39301(11) 0.77806(11) 0.0283(5) Uani d . . . 1 . .
H H39A 0.830493 0.404272 0.800631 0.042 Uiso calc U . R 1 . .
H H39B 0.747572 0.365787 0.735065 0.042 Uiso calc U . R 1 . .
H H39C 0.684424 0.36307 0.809214 0.042 Uiso calc U . R 1 . .
C C40 0.3316(2) 0.64445(10) 0.87615(10) 0.0224(4) Uani d . . . 1 . .
H H40 0.280772 0.640398 0.829015 0.027 Uiso calc U . R 1 . .
C C41 0.2274(2) 0.62572(11) 0.92966(10) 0.0272(5) Uani d . . . 1 . .
H H41A 0.194913 0.57493 0.92279 0.041 Uiso calc U . R 1 . .
H H41B 0.146591 0.659154 0.924048 0.041 Uiso calc U . R 1 . .
H H41C 0.273969 0.631079 0.976437 0.041 Uiso calc U . R 1 . .
C C42 0.3818(2) 0.72433(11) 0.88626(12) 0.0330(5) Uani d . . . 1 . .
H H42A 0.435002 0.729261 0.931549 0.049 Uiso calc U . R 1 . .
H H42B 0.300079 0.757216 0.88412 0.049 Uiso calc U . R 1 . .
H H42C 0.44248 0.737439 0.849568 0.049 Uiso calc U . R 1 . .
C C51 0.28088(19) 0.42112(9) 0.78565(9) 0.0163(4) Uani d . . . 1 . .
C C52 0.1812(2) 0.44884(9) 0.82738(9) 0.0175(4) Uani d . . . 1 . .
C C53 0.1493(2) 0.41874(10) 0.88964(9) 0.0194(4) Uani d . . . 1 . .
C C54 0.2224(2) 0.35727(10) 0.91419(9) 0.0199(4) Uani d . . . 1 . .
C C55 0.3228(2) 0.32752(10) 0.87543(9) 0.0198(4) Uani d . . . 1 . .
C C56 0.34853(19) 0.35862(10) 0.81239(9) 0.0178(4) Uani d . . . 1 . .
C C61 0.14322(19) 0.32042(9) 0.65204(9) 0.0161(4) Uani d . . . 1 . .
C C62 0.2082(2) 0.25658(10) 0.62997(10) 0.0214(4) Uani d . . . 1 . .
H H62 0.28407 0.260107 0.601117 0.026 Uiso calc U . R 1 . .
C C63 0.1621(2) 0.18819(10) 0.65012(10) 0.0253(4) Uani d . . . 1 . .
H H63 0.207171 0.14504 0.635302 0.03 Uiso calc U . R 1 . .
C C64 0.0504(2) 0.18213(11) 0.69180(10) 0.0267(5) Uani d . . . 1 . .
H H64 0.020232 0.135233 0.706343 0.032 Uiso calc U . R 1 . .
C C65 -0.0163(2) 0.24553(10) 0.71189(10) 0.0250(4) Uani d . . . 1 . .
H H65 -0.094309 0.241753 0.739339 0.03 Uiso calc U . R 1 . .
C C66 0.0294(2) 0.31445(10) 0.69242(9) 0.0206(4) Uani d . . . 1 . .
H H66 -0.017017 0.357439 0.706668 0.025 Uiso calc U . R 1 . .
F F52 0.10698(12) 0.50954(6) 0.80580(5) 0.0231(3) Uani d . . . 1 . .
F F53 0.04915(12) 0.44806(6) 0.92662(5) 0.0271(3) Uani d . . . 1 . .
F F54 0.19614(12) 0.32724(6) 0.97505(5) 0.0267(3) Uani d . . . 1 . .
F F55 0.39446(13) 0.26720(6) 0.89878(6) 0.0301(3) Uani d . . . 1 . .
F F56 0.44438(12) 0.32312(6) 0.77625(5) 0.0245(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 O1 . 1.512(2) ?
B1 C1 . 1.619(3) ?
B1 C18 . 1.636(3) ?
B1 C51 . 1.640(3) ?
N1 C1 . 1.352(2) ?
N1 C2 . 1.384(2) ?
N1 C11 . 1.452(2) ?
N2 C1 . 1.357(2) ?
N2 C3 . 1.388(2) ?
N2 C31 . 1.453(2) ?
N3 C61 . 1.419(2) ?
N3 O1 . 1.4810(18) ?
N3 C18 . 1.503(2) ?
C2 C3 . 1.338(3) ?
C2 H2 . 0.95 ?
C3 H3 . 0.95 ?
C11 C16 . 1.396(3) ?
C11 C12 . 1.397(3) ?
C12 C13 . 1.392(3) ?
C12 C17 . 1.528(3) ?
C13 C14 . 1.389(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.383(3) ?
C14 H14 . 0.95 ?
C15 C16 . 1.398(3) ?
C15 H15 . 0.95 ?
C16 C20 . 1.520(3) ?
C17 C19 . 1.530(2) ?
C17 C18 . 1.547(2) ?
C17 H17 . 1.0 ?
C18 H18 . 1.0 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C20 C22 . 1.531(3) ?
C20 C21 . 1.533(3) ?
C20 H20 . 1.0 ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
C31 C36 . 1.403(3) ?
C31 C32 . 1.404(3) ?
C32 C33 . 1.395(3) ?
C32 C37 . 1.520(3) ?
C33 C34 . 1.385(3) ?
C33 H33 . 0.95 ?
C34 C35 . 1.379(3) ?
C34 H34 . 0.95 ?
C35 C36 . 1.399(3) ?
C35 H35 . 0.95 ?
C36 C40 . 1.518(3) ?
C37 C39 . 1.533(3) ?
C37 C38 . 1.533(3) ?
C37 H37 . 1.0 ?
C38 H38A . 0.98 ?
C38 H38B . 0.98 ?
C38 H38C . 0.98 ?
C39 H39A . 0.98 ?
C39 H39B . 0.98 ?
C39 H39C . 0.98 ?
C40 C41 . 1.529(3) ?
C40 C42 . 1.537(3) ?
C40 H40 . 1.0 ?
C41 H41A . 0.98 ?
C41 H41B . 0.98 ?
C41 H41C . 0.98 ?
C42 H42A . 0.98 ?
C42 H42B . 0.98 ?
C42 H42C . 0.98 ?
C51 C56 . 1.386(3) ?
C51 C52 . 1.389(3) ?
C52 F52 . 1.358(2) ?
C52 C53 . 1.379(3) ?
C53 F53 . 1.348(2) ?
C53 C54 . 1.381(3) ?
C54 F54 . 1.340(2) ?
C54 C55 . 1.373(3) ?
C55 F55 . 1.351(2) ?
C55 C56 . 1.384(3) ?
C56 F56 . 1.357(2) ?
C61 C66 . 1.390(3) ?
C61 C62 . 1.399(3) ?
C62 C63 . 1.386(3) ?
C62 H62 . 0.95 ?
C63 C64 . 1.389(3) ?
C63 H63 . 0.95 ?
C64 C65 . 1.387(3) ?
C64 H64 . 0.95 ?
C65 C66 . 1.389(3) ?
C65 H65 . 0.95 ?
C66 H66 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 B1 C1 . . 113.94(14) ?
O1 B1 C18 . . 87.39(13) ?
C1 B1 C18 . . 111.23(15) ?
O1 B1 C51 . . 107.28(14) ?
C1 B1 C51 . . 113.94(15) ?
C18 B1 C51 . . 120.12(15) ?
C1 N1 C2 . . 110.66(15) ?
C1 N1 C11 . . 126.69(15) ?
C2 N1 C11 . . 122.47(15) ?
C1 N2 C3 . . 110.29(14) ?
C1 N2 C31 . . 129.61(15) ?
C3 N2 C31 . . 120.01(15) ?
C61 N3 O1 . . 110.73(13) ?
C61 N3 C18 . . 116.63(14) ?
O1 N3 C18 . . 93.63(12) ?
N3 O1 B1 . . 90.06(12) ?
N1 C1 N2 . . 105.00(15) ?
N1 C1 B1 . . 122.02(15) ?
N2 C1 B1 . . 132.35(15) ?
C3 C2 N1 . . 107.02(16) ?
C3 C2 H2 . . 126.5 ?
N1 C2 H2 . . 126.5 ?
C2 C3 N2 . . 107.01(16) ?
C2 C3 H3 . . 126.5 ?
N2 C3 H3 . . 126.5 ?
C16 C11 C12 . . 124.17(16) ?
C16 C11 N1 . . 117.75(16) ?
C12 C11 N1 . . 118.00(16) ?
C13 C12 C11 . . 116.45(17) ?
C13 C12 C17 . . 122.10(16) ?
C11 C12 C17 . . 121.43(15) ?
C14 C13 C12 . . 121.26(18) ?
C14 C13 H13 . . 119.4 ?
C12 C13 H13 . . 119.4 ?
C15 C14 C13 . . 120.40(17) ?
C15 C14 H14 . . 119.8 ?
C13 C14 H14 . . 119.8 ?
C14 C15 C16 . . 120.90(18) ?
C14 C15 H15 . . 119.6 ?
C16 C15 H15 . . 119.6 ?
C11 C16 C15 . . 116.73(17) ?
C11 C16 C20 . . 123.83(16) ?
C15 C16 C20 . . 119.34(17) ?
C12 C17 C19 . . 112.85(15) ?
C12 C17 C18 . . 111.76(15) ?
C19 C17 C18 . . 109.88(14) ?
C12 C17 H17 . . 107.4 ?
C19 C17 H17 . . 107.4 ?
C18 C17 H17 . . 107.4 ?
N3 C18 C17 . . 109.55(14) ?
N3 C18 B1 . . 84.71(13) ?
C17 C18 B1 . . 118.20(14) ?
N3 C18 H18 . . 113.7 ?
C17 C18 H18 . . 113.7 ?
B1 C18 H18 . . 113.7 ?
C17 C19 H19A . . 109.5 ?
C17 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C17 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C16 C20 C22 . . 111.93(16) ?
C16 C20 C21 . . 110.51(16) ?
C22 C20 C21 . . 110.60(16) ?
C16 C20 H20 . . 107.9 ?
C22 C20 H20 . . 107.9 ?
C21 C20 H20 . . 107.9 ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C20 C22 H22A . . 109.5 ?
C20 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C20 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C36 C31 C32 . . 123.60(16) ?
C36 C31 N2 . . 117.43(16) ?
C32 C31 N2 . . 118.52(16) ?
C33 C32 C31 . . 116.95(17) ?
C33 C32 C37 . . 121.04(17) ?
C31 C32 C37 . . 122.01(16) ?
C34 C33 C32 . . 120.73(18) ?
C34 C33 H33 . . 119.6 ?
C32 C33 H33 . . 119.6 ?
C35 C34 C33 . . 121.04(17) ?
C35 C34 H34 . . 119.5 ?
C33 C34 H34 . . 119.5 ?
C34 C35 C36 . . 121.00(17) ?
C34 C35 H35 . . 119.5 ?
C36 C35 H35 . . 119.5 ?
C35 C36 C31 . . 116.65(17) ?
C35 C36 C40 . . 119.63(17) ?
C31 C36 C40 . . 123.72(16) ?
C32 C37 C39 . . 113.21(16) ?
C32 C37 C38 . . 111.49(16) ?
C39 C37 C38 . . 109.09(17) ?
C32 C37 H37 . . 107.6 ?
C39 C37 H37 . . 107.6 ?
C38 C37 H37 . . 107.6 ?
C37 C38 H38A . . 109.5 ?
C37 C38 H38B . . 109.5 ?
H38A C38 H38B . . 109.5 ?
C37 C38 H38C . . 109.5 ?
H38A C38 H38C . . 109.5 ?
H38B C38 H38C . . 109.5 ?
C37 C39 H39A . . 109.5 ?
C37 C39 H39B . . 109.5 ?
H39A C39 H39B . . 109.5 ?
C37 C39 H39C . . 109.5 ?
H39A C39 H39C . . 109.5 ?
H39B C39 H39C . . 109.5 ?
C36 C40 C41 . . 111.74(16) ?
C36 C40 C42 . . 111.36(16) ?
C41 C40 C42 . . 109.68(17) ?
C36 C40 H40 . . 108.0 ?
C41 C40 H40 . . 108.0 ?
C42 C40 H40 . . 108.0 ?
C40 C41 H41A . . 109.5 ?
C40 C41 H41B . . 109.5 ?
H41A C41 H41B . . 109.5 ?
C40 C41 H41C . . 109.5 ?
H41A C41 H41C . . 109.5 ?
H41B C41 H41C . . 109.5 ?
C40 C42 H42A . . 109.5 ?
C40 C42 H42B . . 109.5 ?
H42A C42 H42B . . 109.5 ?
C40 C42 H42C . . 109.5 ?
H42A C42 H42C . . 109.5 ?
H42B C42 H42C . . 109.5 ?
C56 C51 C52 . . 113.54(16) ?
C56 C51 B1 . . 128.49(16) ?
C52 C51 B1 . . 117.17(15) ?
F52 C52 C53 . . 116.46(16) ?
F52 C52 C51 . . 118.63(15) ?
C53 C52 C51 . . 124.91(16) ?
F53 C53 C52 . . 121.44(16) ?
F53 C53 C54 . . 119.76(16) ?
C52 C53 C54 . . 118.80(17) ?
F54 C54 C55 . . 120.46(16) ?
F54 C54 C53 . . 120.53(17) ?
C55 C54 C53 . . 119.01(17) ?
F55 C55 C54 . . 119.54(16) ?
F55 C55 C56 . . 120.38(17) ?
C54 C55 C56 . . 120.07(16) ?
F56 C56 C55 . . 115.72(15) ?
F56 C56 C51 . . 120.63(16) ?
C55 C56 C51 . . 123.63(17) ?
C66 C61 C62 . . 119.39(17) ?
C66 C61 N3 . . 121.47(16) ?
C62 C61 N3 . . 118.99(17) ?
C63 C62 C61 . . 120.08(18) ?
C63 C62 H62 . . 120.0 ?
C61 C62 H62 . . 120.0 ?
C62 C63 C64 . . 120.62(18) ?
C62 C63 H63 . . 119.7 ?
C64 C63 H63 . . 119.7 ?
C65 C64 C63 . . 119.06(18) ?
C65 C64 H64 . . 120.5 ?
C63 C64 H64 . . 120.5 ?
C64 C65 C66 . . 120.92(19) ?
C64 C65 H65 . . 119.5 ?
C66 C65 H65 . . 119.5 ?
C65 C66 C61 . . 119.89(18) ?
C65 C66 H66 . . 120.1 ?
C61 C66 H66 . . 120.1 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C61 N3 O1 B1 . . . . 103.80(14) ?
C18 N3 O1 B1 . . . . -16.49(13) ?
C1 B1 O1 N3 . . . . 127.22(15) ?
C18 B1 O1 N3 . . . . 15.10(12) ?
C51 B1 O1 N3 . . . . -105.69(14) ?
C2 N1 C1 N2 . . . . 0.1(2) ?
C11 N1 C1 N2 . . . . 175.24(16) ?
C2 N1 C1 B1 . . . . -171.87(16) ?
C11 N1 C1 B1 . . . . 3.3(3) ?
C3 N2 C1 N1 . . . . 0.1(2) ?
C31 N2 C1 N1 . . . . -176.45(17) ?
C3 N2 C1 B1 . . . . 170.81(18) ?
C31 N2 C1 B1 . . . . -5.7(3) ?
O1 B1 C1 N1 . . . . -41.4(2) ?
C18 B1 C1 N1 . . . . 55.4(2) ?
C51 B1 C1 N1 . . . . -164.99(16) ?
O1 B1 C1 N2 . . . . 149.12(18) ?
C18 B1 C1 N2 . . . . -114.0(2) ?
C51 B1 C1 N2 . . . . 25.6(3) ?
C1 N1 C2 C3 . . . . -0.2(2) ?
C11 N1 C2 C3 . . . . -175.59(17) ?
N1 C2 C3 N2 . . . . 0.2(2) ?
C1 N2 C3 C2 . . . . -0.2(2) ?
C31 N2 C3 C2 . . . . 176.72(16) ?
C1 N1 C11 C16 . . . . 125.97(19) ?
C2 N1 C11 C16 . . . . -59.4(2) ?
C1 N1 C11 C12 . . . . -57.3(3) ?
C2 N1 C11 C12 . . . . 117.32(19) ?
C16 C11 C12 C13 . . . . 2.6(3) ?
N1 C11 C12 C13 . . . . -173.90(15) ?
C16 C11 C12 C17 . . . . -175.80(17) ?
N1 C11 C12 C17 . . . . 7.7(3) ?
C11 C12 C13 C14 . . . . 0.1(3) ?
C17 C12 C13 C14 . . . . 178.53(17) ?
C12 C13 C14 C15 . . . . -1.7(3) ?
C13 C14 C15 C16 . . . . 0.7(3) ?
C12 C11 C16 C15 . . . . -3.5(3) ?
N1 C11 C16 C15 . . . . 172.94(16) ?
C12 C11 C16 C20 . . . . 172.70(17) ?
N1 C11 C16 C20 . . . . -10.8(3) ?
C14 C15 C16 C11 . . . . 1.8(3) ?
C14 C15 C16 C20 . . . . -174.62(17) ?
C13 C12 C17 C19 . . . . 13.7(2) ?
C11 C12 C17 C19 . . . . -168.03(16) ?
C13 C12 C17 C18 . . . . -110.75(19) ?
C11 C12 C17 C18 . . . . 67.5(2) ?
C61 N3 C18 C17 . . . . 141.80(15) ?
O1 N3 C18 C17 . . . . -102.82(14) ?
C61 N3 C18 B1 . . . . -100.11(15) ?
O1 N3 C18 B1 . . . . 15.27(12) ?
C12 C17 C18 N3 . . . . 39.93(19) ?
C19 C17 C18 N3 . . . . -86.15(17) ?
C12 C17 C18 B1 . . . . -54.6(2) ?
C19 C17 C18 B1 . . . . 179.30(15) ?
O1 B1 C18 N3 . . . . -14.94(11) ?
C1 B1 C18 N3 . . . . -129.66(14) ?
C51 B1 C18 N3 . . . . 93.56(17) ?
O1 B1 C18 C17 . . . . 94.43(16) ?
C1 B1 C18 C17 . . . . -20.3(2) ?
C51 B1 C18 C17 . . . . -157.07(16) ?
C11 C16 C20 C22 . . . . 117.8(2) ?
C15 C16 C20 C22 . . . . -66.0(2) ?
C11 C16 C20 C21 . . . . -118.40(19) ?
C15 C16 C20 C21 . . . . 57.7(2) ?
C1 N2 C31 C36 . . . . -111.0(2) ?
C3 N2 C31 C36 . . . . 72.8(2) ?
C1 N2 C31 C32 . . . . 76.5(2) ?
C3 N2 C31 C32 . . . . -99.7(2) ?
C36 C31 C32 C33 . . . . -0.6(3) ?
N2 C31 C32 C33 . . . . 171.40(16) ?
C36 C31 C32 C37 . . . . -179.86(17) ?
N2 C31 C32 C37 . . . . -7.8(3) ?
C31 C32 C33 C34 . . . . -1.3(3) ?
C37 C32 C33 C34 . . . . 177.94(17) ?
C32 C33 C34 C35 . . . . 2.0(3) ?
C33 C34 C35 C36 . . . . -0.7(3) ?
C34 C35 C36 C31 . . . . -1.1(3) ?
C34 C35 C36 C40 . . . . 178.99(18) ?
C32 C31 C36 C35 . . . . 1.8(3) ?
N2 C31 C36 C35 . . . . -170.29(16) ?
C32 C31 C36 C40 . . . . -178.30(17) ?
N2 C31 C36 C40 . . . . 9.6(3) ?
C33 C32 C37 C39 . . . . 23.1(3) ?
C31 C32 C37 C39 . . . . -157.67(17) ?
C33 C32 C37 C38 . . . . -100.3(2) ?
C31 C32 C37 C38 . . . . 78.9(2) ?
C35 C36 C40 C41 . . . . -51.3(2) ?
C31 C36 C40 C41 . . . . 128.76(19) ?
C35 C36 C40 C42 . . . . 71.7(2) ?
C31 C36 C40 C42 . . . . -108.2(2) ?
O1 B1 C51 C56 . . . . 113.66(19) ?
C1 B1 C51 C56 . . . . -119.2(2) ?
C18 B1 C51 C56 . . . . 16.5(3) ?
O1 B1 C51 C52 . . . . -55.4(2) ?
C1 B1 C51 C52 . . . . 71.7(2) ?
C18 B1 C51 C52 . . . . -152.55(17) ?
C56 C51 C52 F52 . . . . -179.14(15) ?
B1 C51 C52 F52 . . . . -8.5(2) ?
C56 C51 C52 C53 . . . . -0.1(3) ?
B1 C51 C52 C53 . . . . 170.55(17) ?
F52 C52 C53 F53 . . . . 0.4(3) ?
C51 C52 C53 F53 . . . . -178.71(17) ?
F52 C52 C53 C54 . . . . -179.57(15) ?
C51 C52 C53 C54 . . . . 1.4(3) ?
F53 C53 C54 F54 . . . . -1.1(3) ?
C52 C53 C54 F54 . . . . 178.82(16) ?
F53 C53 C54 C55 . . . . 179.13(17) ?
C52 C53 C54 C55 . . . . -0.9(3) ?
F54 C54 C55 F55 . . . . 0.5(3) ?
C53 C54 C55 F55 . . . . -179.71(16) ?
F54 C54 C55 C56 . . . . 179.56(16) ?
C53 C54 C55 C56 . . . . -0.7(3) ?
F55 C55 C56 F56 . . . . 2.3(3) ?
C54 C55 C56 F56 . . . . -176.73(16) ?
F55 C55 C56 C51 . . . . -178.89(16) ?
C54 C55 C56 C51 . . . . 2.1(3) ?
C52 C51 C56 F56 . . . . 177.11(15) ?
B1 C51 C56 F56 . . . . 7.8(3) ?
C52 C51 C56 C55 . . . . -1.6(3) ?
B1 C51 C56 C55 . . . . -170.98(18) ?
O1 N3 C61 C66 . . . . 20.8(2) ?
C18 N3 C61 C66 . . . . 126.25(18) ?
O1 N3 C61 C62 . . . . -163.62(14) ?
C18 N3 C61 C62 . . . . -58.2(2) ?
C66 C61 C62 C63 . . . . -2.0(3) ?
N3 C61 C62 C63 . . . . -177.66(16) ?
C61 C62 C63 C64 . . . . 0.6(3) ?
C62 C63 C64 C65 . . . . 1.3(3) ?
C63 C64 C65 C66 . . . . -1.7(3) ?
C64 C65 C66 C61 . . . . 0.2(3) ?
C62 C61 C66 C65 . . . . 1.6(3) ?
N3 C61 C66 C65 . . . . 177.16(16) ?


####################################################################### 
# 
# 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_11_erk10270
_database_code_depnum_ccdc_archive 'CCDC 2157866'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2022-03-11 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;

_audit_creation_method           'APEX4 v2021.4-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H33 B F6 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         582.42

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.2547(2)
_cell_length_b                   17.4775(4)
_cell_length_c                   16.6351(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.4970(10)
_cell_angle_gamma                90
_cell_volume                     2948.73(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9918
_cell_measurement_theta_min      2.3306
_cell_measurement_theta_max      27.3457
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.079
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1216

_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Mo ImS'
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          'single crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            70471
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_refine_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_number_total             6727
_reflns_number_gt                5412
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.1006
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_number_reflns         6727
_refine_ls_number_parameters     386
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0369P)²+1.3752P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.190
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX4 v2021.4-0 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1242)'
_computing_publication_material  'SHELXT 2018/2 (Sheldrick, 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.60769(14) 0.60482(8) 0.30432(9) 0.0188(3) Uani d . . . 1 . .
N N1 0.52379(10) 0.52555(6) 0.17166(6) 0.0170(2) Uani d . . . 1 . .
N N2 0.60244(10) 0.45373(6) 0.27242(6) 0.0170(2) Uani d . . . 1 . .
F F1 0.66623(8) 0.58526(4) 0.38440(5) 0.02278(17) Uani d . . . 1 . .
C C1 0.56785(12) 0.52666(7) 0.25243(8) 0.0169(2) Uani d . . . 1 . .
C C2 0.53303(13) 0.45198(7) 0.14096(8) 0.0188(3) Uani d . . . 1 . .
H H2 0.509283 0.436425 0.086029 0.023000 Uiso calc U . R 1 . .
C C3 0.58196(13) 0.40719(7) 0.20387(8) 0.0189(3) Uani d . . . 1 . .
H H3 0.599285 0.353873 0.201914 0.023000 Uiso calc U . R 1 . .
C C11 0.48160(13) 0.59152(7) 0.12218(8) 0.0179(2) Uani d . . . 1 . .
C C12 0.56935(13) 0.65362(7) 0.12108(8) 0.0203(3) Uani d . . . 1 . .
C C13 0.52975(14) 0.71223(8) 0.06507(9) 0.0250(3) Uani d . . . 1 . .
H H13 0.587342 0.754236 0.061340 0.030000 Uiso calc U . R 1 . .
C C14 0.40947(15) 0.71057(8) 0.01524(9) 0.0266(3) Uani d . . . 1 . .
H H14 0.385706 0.750848 -0.022425 0.032000 Uiso calc U . R 1 . .
C C15 0.32325(14) 0.65007(8) 0.02015(8) 0.0237(3) Uani d . . . 1 . .
H H15 0.239905 0.650052 -0.013503 0.028000 Uiso calc U . R 1 . .
C C16 0.35679(13) 0.58927(7) 0.07363(8) 0.0193(3) Uani d . . . 1 . .
C C17 0.69858(13) 0.66086(7) 0.17477(9) 0.0224(3) Uani d . . . 1 . .
C C18 0.71448(13) 0.64180(7) 0.25365(8) 0.0216(3) Uani d . . . 1 . .
H H18 0.799310 0.651278 0.283455 0.026000 Uiso calc U . R 1 . .
C C19 0.80891(14) 0.69800(9) 0.13721(9) 0.0290(3) Uani d . . . 1 . .
H H19A 0.791960 0.753007 0.130822 0.043000 Uiso calc U . R 1 . .
H H19B 0.813095 0.675097 0.083874 0.043000 Uiso calc U . R 1 . .
H H19C 0.892949 0.689880 0.172654 0.043000 Uiso calc U . R 1 . .
C C20 0.25653(13) 0.52541(8) 0.07737(8) 0.0211(3) Uani d . . . 1 . .
H H20 0.290011 0.491311 0.124161 0.025000 Uiso calc U . R 1 . .
C C21 0.23973(15) 0.47703(8) -0.00064(9) 0.0274(3) Uani d . . . 1 . .
H H21A 0.207528 0.509544 -0.047374 0.041000 Uiso calc U . R 1 . .
H H21B 0.176100 0.435957 0.003711 0.041000 Uiso calc U . R 1 . .
H H21C 0.324868 0.454749 -0.008004 0.041000 Uiso calc U . R 1 . .
C C22 0.12243(14) 0.55731(9) 0.09125(9) 0.0271(3) Uani d . . . 1 . .
H H22A 0.134212 0.590744 0.139064 0.041000 Uiso calc U . R 1 . .
H H22B 0.063642 0.514918 0.100126 0.041000 Uiso calc U . R 1 . .
H H22C 0.083675 0.586656 0.043428 0.041000 Uiso calc U . R 1 . .
C C31 0.65912(13) 0.42597(7) 0.35232(7) 0.0174(2) Uani d . . . 1 . .
C C32 0.57443(13) 0.39450(7) 0.40216(8) 0.0194(3) Uani d . . . 1 . .
C C33 0.63206(14) 0.36910(7) 0.47892(8) 0.0234(3) Uani d . . . 1 . .
H H33 0.577990 0.347878 0.514952 0.028000 Uiso calc U . R 1 . .
C C34 0.76683(14) 0.37443(8) 0.50317(8) 0.0244(3) Uani d . . . 1 . .
H H34 0.804066 0.357637 0.555897 0.029000 Uiso calc U . R 1 . .
C C35 0.84797(13) 0.40412(7) 0.45105(8) 0.0217(3) Uani d . . . 1 . .
H H35 0.940480 0.406302 0.468129 0.026000 Uiso calc U . R 1 . .
C C36 0.79582(13) 0.43077(7) 0.37412(8) 0.0191(3) Uani d . . . 1 . .
C C37 0.42568(13) 0.39083(8) 0.37627(9) 0.0237(3) Uani d . . . 1 . .
H H37 0.407792 0.395586 0.315732 0.028000 Uiso calc U . R 1 . .
C C38 0.36100(15) 0.45893(9) 0.41269(10) 0.0310(3) Uani d . . . 1 . .
H H38A 0.371000 0.453344 0.471898 0.046000 Uiso calc U . R 1 . .
H H38B 0.267053 0.460608 0.390456 0.046000 Uiso calc U . R 1 . .
H H38C 0.403518 0.506431 0.399024 0.046000 Uiso calc U . R 1 . .
C C39 0.36581(16) 0.31519(9) 0.39980(11) 0.0367(4) Uani d . . . 1 . .
H H39A 0.413430 0.272326 0.379658 0.055000 Uiso calc U . R 1 . .
H H39B 0.272727 0.312906 0.375687 0.055000 Uiso calc U . R 1 . .
H H39C 0.372971 0.311976 0.459105 0.055000 Uiso calc U . R 1 . .
C C40 0.88659(13) 0.46207(8) 0.31779(8) 0.0228(3) Uani d . . . 1 . .
H H40 0.830616 0.486606 0.270447 0.027000 Uiso calc U . R 1 . .
C C41 0.98028(14) 0.52292(8) 0.35946(9) 0.0286(3) Uani d . . . 1 . .
H H41A 0.929221 0.562755 0.382188 0.043000 Uiso calc U . R 1 . .
H H41B 1.030230 0.545771 0.319667 0.043000 Uiso calc U . R 1 . .
H H41C 1.041444 0.499219 0.403248 0.043000 Uiso calc U . R 1 . .
C C42 0.96385(16) 0.39679(10) 0.28528(10) 0.0357(4) Uani d . . . 1 . .
H H42A 1.018115 0.371056 0.330775 0.054000 Uiso calc U . R 1 . .
H H42B 1.020789 0.417588 0.248180 0.054000 Uiso calc U . R 1 . .
H H42C 0.902037 0.359986 0.256084 0.054000 Uiso calc U . R 1 . .
C C51 0.48523(13) 0.66397(7) 0.31188(7) 0.0186(3) Uani d . . . 1 . .
C C52 0.35109(13) 0.65131(7) 0.29088(8) 0.0200(3) Uani d . . . 1 . .
C C53 0.25514(13) 0.70470(8) 0.30160(8) 0.0244(3) Uani d . . . 1 . .
C C54 0.29248(15) 0.77380(8) 0.33796(9) 0.0272(3) Uani d . . . 1 . .
C C55 0.42435(15) 0.78872(7) 0.36197(8) 0.0249(3) Uani d . . . 1 . .
C C56 0.51675(13) 0.73479(7) 0.34790(8) 0.0207(3) Uani d . . . 1 . .
F F52 0.30697(8) 0.58325(4) 0.25889(5) 0.02513(18) Uani d . . . 1 . .
F F53 0.12627(8) 0.68900(5) 0.27966(6) 0.0339(2) Uani d . . . 1 . .
F F54 0.20087(10) 0.82574(5) 0.35068(6) 0.0404(2) Uani d . . . 1 . .
F F55 0.46181(10) 0.85562(5) 0.39904(5) 0.0342(2) Uani d . . . 1 . .
F F56 0.64445(8) 0.75355(4) 0.37222(5) 0.02654(18) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 F1 . 1.4196(16) ?
B1 C18 . 1.613(2) ?
B1 C1 . 1.6351(18) ?
B1 C51 . 1.6458(19) ?
N1 C1 . 1.3528(16) ?
N1 C2 . 1.3920(16) ?
N1 C11 . 1.4453(16) ?
N2 C1 . 1.3514(16) ?
N2 C3 . 1.3912(16) ?
N2 C31 . 1.4532(16) ?
C2 C3 . 1.3433(18) ?
C2 H2 . 0.950000 ?
C3 H3 . 0.950000 ?
C11 C16 . 1.4095(18) ?
C11 C12 . 1.4117(18) ?
C12 C13 . 1.4037(18) ?
C12 C17 . 1.4900(19) ?
C13 C14 . 1.381(2) ?
C13 H13 . 0.950000 ?
C14 C15 . 1.388(2) ?
C14 H14 . 0.950000 ?
C15 C16 . 1.3958(18) ?
C15 H15 . 0.950000 ?
C16 C20 . 1.5250(18) ?
C17 C18 . 1.340(2) ?
C17 C19 . 1.5168(19) ?
C18 H18 . 0.950000 ?
C19 H19A . 0.980000 ?
C19 H19B . 0.980000 ?
C19 H19C . 0.980000 ?
C20 C22 . 1.5327(19) ?
C20 C21 . 1.5371(19) ?
C20 H20 . 1.000000 ?
C21 H21A . 0.980000 ?
C21 H21B . 0.980000 ?
C21 H21C . 0.980000 ?
C22 H22A . 0.980000 ?
C22 H22B . 0.980000 ?
C22 H22C . 0.980000 ?
C31 C36 . 1.3977(18) ?
C31 C32 . 1.3989(18) ?
C32 C33 . 1.3977(19) ?
C32 C37 . 1.5239(19) ?
C33 C34 . 1.384(2) ?
C33 H33 . 0.950000 ?
C34 C35 . 1.388(2) ?
C34 H34 . 0.950000 ?
C35 C36 . 1.3922(18) ?
C35 H35 . 0.950000 ?
C36 C40 . 1.5171(18) ?
C37 C38 . 1.5305(19) ?
C37 C39 . 1.533(2) ?
C37 H37 . 1.000000 ?
C38 H38A . 0.980000 ?
C38 H38B . 0.980000 ?
C38 H38C . 0.980000 ?
C39 H39A . 0.980000 ?
C39 H39B . 0.980000 ?
C39 H39C . 0.980000 ?
C40 C41 . 1.5290(19) ?
C40 C42 . 1.532(2) ?
C40 H40 . 1.000000 ?
C41 H41A . 0.980000 ?
C41 H41B . 0.980000 ?
C41 H41C . 0.980000 ?
C42 H42A . 0.980000 ?
C42 H42B . 0.980000 ?
C42 H42C . 0.980000 ?
C51 C52 . 1.3860(19) ?
C51 C56 . 1.3924(18) ?
C52 F52 . 1.3533(15) ?
C52 C53 . 1.3866(19) ?
C53 F53 . 1.3462(16) ?
C53 C54 . 1.379(2) ?
C54 F54 . 1.3453(16) ?
C54 C55 . 1.377(2) ?
C55 F55 . 1.3509(15) ?
C55 C56 . 1.3807(19) ?
C56 F56 . 1.3525(16) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 B1 C18 . . 111.18(11) ?
F1 B1 C1 . . 109.41(10) ?
C18 B1 C1 . . 101.24(10) ?
F1 B1 C51 . . 107.52(10) ?
C18 B1 C51 . . 111.90(10) ?
C1 B1 C51 . . 115.54(11) ?
C1 N1 C2 . . 110.29(10) ?
C1 N1 C11 . . 125.60(10) ?
C2 N1 C11 . . 123.97(10) ?
C1 N2 C3 . . 110.34(10) ?
C1 N2 C31 . . 126.50(10) ?
C3 N2 C31 . . 123.10(10) ?
N2 C1 N1 . . 105.53(10) ?
N2 C1 B1 . . 128.46(11) ?
N1 C1 B1 . . 123.85(11) ?
C3 C2 N1 . . 106.88(11) ?
C3 C2 H2 . . 126.600000 ?
N1 C2 H2 . . 126.600000 ?
C2 C3 N2 . . 106.95(11) ?
C2 C3 H3 . . 126.500000 ?
N2 C3 H3 . . 126.500000 ?
C16 C11 C12 . . 122.72(12) ?
C16 C11 N1 . . 118.31(11) ?
C12 C11 N1 . . 118.88(11) ?
C13 C12 C11 . . 116.57(12) ?
C13 C12 C17 . . 118.71(12) ?
C11 C12 C17 . . 124.73(12) ?
C14 C13 C12 . . 121.88(13) ?
C14 C13 H13 . . 119.100000 ?
C12 C13 H13 . . 119.100000 ?
C13 C14 C15 . . 120.05(13) ?
C13 C14 H14 . . 120.000000 ?
C15 C14 H14 . . 120.000000 ?
C14 C15 C16 . . 121.21(13) ?
C14 C15 H15 . . 119.400000 ?
C16 C15 H15 . . 119.400000 ?
C15 C16 C11 . . 117.48(12) ?
C15 C16 C20 . . 118.62(12) ?
C11 C16 C20 . . 123.89(11) ?
C18 C17 C12 . . 122.31(12) ?
C18 C17 C19 . . 121.30(13) ?
C12 C17 C19 . . 116.16(12) ?
C17 C18 B1 . . 128.14(12) ?
C17 C18 H18 . . 115.900000 ?
B1 C18 H18 . . 115.900000 ?
C17 C19 H19A . . 109.500000 ?
C17 C19 H19B . . 109.500000 ?
H19A C19 H19B . . 109.500000 ?
C17 C19 H19C . . 109.500000 ?
H19A C19 H19C . . 109.500000 ?
H19B C19 H19C . . 109.500000 ?
C16 C20 C22 . . 111.43(11) ?
C16 C20 C21 . . 111.12(11) ?
C22 C20 C21 . . 109.64(11) ?
C16 C20 H20 . . 108.200000 ?
C22 C20 H20 . . 108.200000 ?
C21 C20 H20 . . 108.200000 ?
C20 C21 H21A . . 109.500000 ?
C20 C21 H21B . . 109.500000 ?
H21A C21 H21B . . 109.500000 ?
C20 C21 H21C . . 109.500000 ?
H21A C21 H21C . . 109.500000 ?
H21B C21 H21C . . 109.500000 ?
C20 C22 H22A . . 109.500000 ?
C20 C22 H22B . . 109.500000 ?
H22A C22 H22B . . 109.500000 ?
C20 C22 H22C . . 109.500000 ?
H22A C22 H22C . . 109.500000 ?
H22B C22 H22C . . 109.500000 ?
C36 C31 C32 . . 123.82(12) ?
C36 C31 N2 . . 117.87(11) ?
C32 C31 N2 . . 118.29(11) ?
C33 C32 C31 . . 116.78(12) ?
C33 C32 C37 . . 121.02(12) ?
C31 C32 C37 . . 122.15(12) ?
C34 C33 C32 . . 120.92(13) ?
C34 C33 H33 . . 119.500000 ?
C32 C33 H33 . . 119.500000 ?
C33 C34 C35 . . 120.53(12) ?
C33 C34 H34 . . 119.700000 ?
C35 C34 H34 . . 119.700000 ?
C34 C35 C36 . . 120.99(13) ?
C34 C35 H35 . . 119.500000 ?
C36 C35 H35 . . 119.500000 ?
C35 C36 C31 . . 116.92(12) ?
C35 C36 C40 . . 120.06(12) ?
C31 C36 C40 . . 123.01(12) ?
C32 C37 C38 . . 109.25(11) ?
C32 C37 C39 . . 112.72(12) ?
C38 C37 C39 . . 110.87(12) ?
C32 C37 H37 . . 107.900000 ?
C38 C37 H37 . . 107.900000 ?
C39 C37 H37 . . 107.900000 ?
C37 C38 H38A . . 109.500000 ?
C37 C38 H38B . . 109.500000 ?
H38A C38 H38B . . 109.500000 ?
C37 C38 H38C . . 109.500000 ?
H38A C38 H38C . . 109.500000 ?
H38B C38 H38C . . 109.500000 ?
C37 C39 H39A . . 109.500000 ?
C37 C39 H39B . . 109.500000 ?
H39A C39 H39B . . 109.500000 ?
C37 C39 H39C . . 109.500000 ?
H39A C39 H39C . . 109.500000 ?
H39B C39 H39C . . 109.500000 ?
C36 C40 C41 . . 111.87(11) ?
C36 C40 C42 . . 110.24(11) ?
C41 C40 C42 . . 110.78(12) ?
C36 C40 H40 . . 107.900000 ?
C41 C40 H40 . . 107.900000 ?
C42 C40 H40 . . 107.900000 ?
C40 C41 H41A . . 109.500000 ?
C40 C41 H41B . . 109.500000 ?
H41A C41 H41B . . 109.500000 ?
C40 C41 H41C . . 109.500000 ?
H41A C41 H41C . . 109.500000 ?
H41B C41 H41C . . 109.500000 ?
C40 C42 H42A . . 109.500000 ?
C40 C42 H42B . . 109.500000 ?
H42A C42 H42B . . 109.500000 ?
C40 C42 H42C . . 109.500000 ?
H42A C42 H42C . . 109.500000 ?
H42B C42 H42C . . 109.500000 ?
C52 C51 C56 . . 114.15(12) ?
C52 C51 B1 . . 128.36(11) ?
C56 C51 B1 . . 117.39(11) ?
F52 C52 C51 . . 120.08(11) ?
F52 C52 C53 . . 116.08(12) ?
C51 C52 C53 . . 123.84(12) ?
F53 C53 C54 . . 119.68(12) ?
F53 C53 C52 . . 120.98(13) ?
C54 C53 C52 . . 119.30(13) ?
F54 C54 C55 . . 120.35(13) ?
F54 C54 C53 . . 120.30(14) ?
C55 C54 C53 . . 119.34(12) ?
F55 C55 C54 . . 119.80(12) ?
F55 C55 C56 . . 120.81(13) ?
C54 C55 C56 . . 119.38(12) ?
F56 C56 C55 . . 116.24(12) ?
F56 C56 C51 . . 119.82(12) ?
C55 C56 C51 . . 123.94(13) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 N2 C1 N1 . . . . 0.94(14) ?
C31 N2 C1 N1 . . . . 178.18(11) ?
C3 N2 C1 B1 . . . . -162.63(12) ?
C31 N2 C1 B1 . . . . 14.6(2) ?
C2 N1 C1 N2 . . . . -1.01(14) ?
C11 N1 C1 N2 . . . . -176.93(11) ?
C2 N1 C1 B1 . . . . 163.52(11) ?
C11 N1 C1 B1 . . . . -12.39(19) ?
F1 B1 C1 N2 . . . . -11.43(18) ?
C18 B1 C1 N2 . . . . 106.00(14) ?
C51 B1 C1 N2 . . . . -132.91(13) ?
F1 B1 C1 N1 . . . . -172.28(11) ?
C18 B1 C1 N1 . . . . -54.85(15) ?
C51 B1 C1 N1 . . . . 66.25(16) ?
C1 N1 C2 C3 . . . . 0.71(14) ?
C11 N1 C2 C3 . . . . 176.70(11) ?
N1 C2 C3 N2 . . . . -0.11(14) ?
C1 N2 C3 C2 . . . . -0.53(14) ?
C31 N2 C3 C2 . . . . -177.88(11) ?
C1 N1 C11 C16 . . . . -127.44(13) ?
C2 N1 C11 C16 . . . . 57.18(17) ?
C1 N1 C11 C12 . . . . 55.89(17) ?
C2 N1 C11 C12 . . . . -119.49(14) ?
C16 C11 C12 C13 . . . . -3.69(19) ?
N1 C11 C12 C13 . . . . 172.83(11) ?
C16 C11 C12 C17 . . . . 176.09(12) ?
N1 C11 C12 C17 . . . . -7.39(19) ?
C11 C12 C13 C14 . . . . 1.9(2) ?
C17 C12 C13 C14 . . . . -177.87(13) ?
C12 C13 C14 C15 . . . . 0.6(2) ?
C13 C14 C15 C16 . . . . -1.5(2) ?
C14 C15 C16 C11 . . . . -0.2(2) ?
C14 C15 C16 C20 . . . . 178.73(13) ?
C12 C11 C16 C15 . . . . 2.88(19) ?
N1 C11 C16 C15 . . . . -173.65(11) ?
C12 C11 C16 C20 . . . . -176.01(12) ?
N1 C11 C16 C20 . . . . 7.45(18) ?
C13 C12 C17 C18 . . . . 138.58(14) ?
C11 C12 C17 C18 . . . . -41.2(2) ?
C13 C12 C17 C19 . . . . -35.96(18) ?
C11 C12 C17 C19 . . . . 144.27(13) ?
C12 C17 C18 B1 . . . . 3.5(2) ?
C19 C17 C18 B1 . . . . 177.79(12) ?
F1 B1 C18 C17 . . . . 173.63(12) ?
C1 B1 C18 C17 . . . . 57.50(16) ?
C51 B1 C18 C17 . . . . -66.12(17) ?
C15 C16 C20 C22 . . . . -52.45(16) ?
C11 C16 C20 C22 . . . . 126.43(13) ?
C15 C16 C20 C21 . . . . 70.14(16) ?
C11 C16 C20 C21 . . . . -110.98(14) ?
C1 N2 C31 C36 . . . . -85.63(15) ?
C3 N2 C31 C36 . . . . 91.28(15) ?
C1 N2 C31 C32 . . . . 95.79(15) ?
C3 N2 C31 C32 . . . . -87.30(15) ?
C36 C31 C32 C33 . . . . 2.16(18) ?
N2 C31 C32 C33 . . . . -179.36(11) ?
C36 C31 C32 C37 . . . . 179.61(12) ?
N2 C31 C32 C37 . . . . -1.90(18) ?
C31 C32 C33 C34 . . . . -0.72(19) ?
C37 C32 C33 C34 . . . . -178.20(12) ?
C32 C33 C34 C35 . . . . -1.0(2) ?
C33 C34 C35 C36 . . . . 1.5(2) ?
C34 C35 C36 C31 . . . . -0.11(18) ?
C34 C35 C36 C40 . . . . -179.24(12) ?
C32 C31 C36 C35 . . . . -1.75(18) ?
N2 C31 C36 C35 . . . . 179.76(11) ?
C32 C31 C36 C40 . . . . 177.35(12) ?
N2 C31 C36 C40 . . . . -1.14(18) ?
C33 C32 C37 C38 . . . . 80.40(15) ?
C31 C32 C37 C38 . . . . -96.95(14) ?
C33 C32 C37 C39 . . . . -43.33(17) ?
C31 C32 C37 C39 . . . . 139.32(13) ?
C35 C36 C40 C41 . . . . -51.40(16) ?
C31 C36 C40 C41 . . . . 129.53(13) ?
C35 C36 C40 C42 . . . . 72.35(16) ?
C31 C36 C40 C42 . . . . -106.72(15) ?
F1 B1 C51 C52 . . . . -111.79(14) ?
C18 B1 C51 C52 . . . . 125.85(14) ?
C1 B1 C51 C52 . . . . 10.70(19) ?
F1 B1 C51 C56 . . . . 64.28(14) ?
C18 B1 C51 C56 . . . . -58.08(15) ?
C1 B1 C51 C56 . . . . -173.23(11) ?
C56 C51 C52 F52 . . . . -176.88(11) ?
B1 C51 C52 F52 . . . . -0.7(2) ?
C56 C51 C52 C53 . . . . 2.17(19) ?
B1 C51 C52 C53 . . . . 178.34(13) ?
F52 C52 C53 F53 . . . . -1.15(18) ?
C51 C52 C53 F53 . . . . 179.77(12) ?
F52 C52 C53 C54 . . . . 176.51(12) ?
C51 C52 C53 C54 . . . . -2.6(2) ?
F53 C53 C54 F54 . . . . -0.8(2) ?
C52 C53 C54 F54 . . . . -178.46(12) ?
F53 C53 C54 C55 . . . . 178.48(12) ?
C52 C53 C54 C55 . . . . 0.8(2) ?
F54 C54 C55 F55 . . . . 0.5(2) ?
C53 C54 C55 F55 . . . . -178.74(12) ?
F54 C54 C55 C56 . . . . -179.62(12) ?
C53 C54 C55 C56 . . . . 1.1(2) ?
F55 C55 C56 F56 . . . . -0.85(19) ?
C54 C55 C56 F56 . . . . 179.29(12) ?
F55 C55 C56 C51 . . . . 178.37(12) ?
C54 C55 C56 C51 . . . . -1.5(2) ?
C52 C51 C56 F56 . . . . 179.07(11) ?
B1 C51 C56 F56 . . . . 2.44(17) ?
C52 C51 C56 C55 . . . . -0.12(19) ?
B1 C51 C56 C55 . . . . -176.74(12) ?



#=============================================================================
#  end of cif data for "erk10270" (compound 11)
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================
####################################################################### 
# 
# 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_6_erk10125
_database_code_depnum_ccdc_archive 'CCDC 2157864'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2022-03-11 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2019.11-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H38 B F5 N3 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         670.53

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.1129(2)
_cell_length_b                   16.9245(3)
_cell_length_c                   15.4437(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.5270(10)
_cell_angle_gamma                90
_cell_volume                     3431.47(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9937
_cell_measurement_theta_min      4.0362
_cell_measurement_theta_max      66.3108
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow-orange
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.073
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1404

_exptl_absorpt_coefficient_mu    0.803
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;

SADABS-2016/2 - Bruker AXS area detector scaling and absorption
correction. Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M.
& Stalke D., J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   CuK\a
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III Diffractometer'
_diffrn_measurement_device_type  'single crystal'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            76484
_diffrn_reflns_av_R_equivalents  0.0877
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_theta_min         3.63
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_full        66.58
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18

_refine_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.

One C6F5 group is disordered over two positions. Several restraints (SADI,
SAME, ISOR and SIMU) were used in order to improve refinement stability.
;

_reflns_number_total             6046
_reflns_number_gt                4654
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_gt          0.1407
_refine_ls_wR_factor_ref         0.1534
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.061
_refine_ls_number_reflns         6046
_refine_ls_number_parameters     547
_refine_ls_number_restraints     476
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0685P)²+3.0810P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.962
_refine_diff_density_min         -0.296
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
N N 0.0311 0.0180 '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'

_computing_data_collection       'Bruker APEX3 v2019.11-0 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.54777(13) 0.24963(11) 0.73879(12) 0.0264(4) Uani d . . . 1.0 . .
N N3 0.35585(14) 0.21826(11) 0.57610(13) 0.0274(4) Uani d . . . 1.0 . .
O O1 0.33565(13) 0.16146(10) 0.62217(13) 0.0430(5) Uani d . . . 1.0 . .
C C1 0.46582(17) 0.29790(13) 0.71738(15) 0.0270(5) Uani d U . . 1.0 . .
C C2 0.60462(17) 0.25217(14) 0.83366(16) 0.0300(5) Uani d U . . 1.0 . .
H H2 0.665607 0.223898 0.865782 0.036 Uiso calc U . R 1.0 . .
C C3 0.55664(18) 0.30236(14) 0.87114(16) 0.0317(5) Uani d U . . 1.0 . .
H H3 0.577188 0.315959 0.935094 0.038 Uiso calc U . R 1.0 . .
C C11 0.57868(16) 0.20558(14) 0.67326(15) 0.0282(5) Uani d U . . 1.0 . .
C C12 0.59015(18) 0.24797(16) 0.59941(17) 0.0366(6) Uani d U . . 1.0 . .
C C13 0.6255(2) 0.2066(2) 0.54015(19) 0.0510(8) Uani d U . . 1.0 . .
H H13 0.635116 0.233493 0.490013 0.061 Uiso calc U . R 1.0 . .
C C14 0.6469(2) 0.1271(2) 0.5525(2) 0.0588(9) Uani d U . . 1.0 . .
H H14 0.671881 0.100067 0.511408 0.071 Uiso calc U . R 1.0 . .
C C15 0.6324(2) 0.08643(18) 0.62380(18) 0.0471(7) Uani d U . . 1.0 . .
H H15 0.646748 0.031442 0.630668 0.056 Uiso calc U . R 1.0 . .
C C16 0.59701(17) 0.12481(15) 0.68642(16) 0.0316(5) Uani d U . . 1.0 . .
C C17 0.55573(19) 0.33333(16) 0.58015(18) 0.0399(6) Uani d U . . 1.0 . .
H H17 0.576834 0.360877 0.641633 0.048 Uiso calc U . R 1.0 . .
C C18 0.43618(18) 0.33474(14) 0.53700(16) 0.0310(5) Uani d U . . 1.0 . .
H H18 0.412056 0.389259 0.514689 0.037 Uiso calc U . R 1.0 . .
C C19 0.6034(2) 0.3785(2) 0.5205(2) 0.0604(9) Uani d U . . 1.0 . .
H H19A 0.677821 0.375711 0.549649 0.091 Uiso calc U . R 1.0 . .
H H19B 0.581739 0.433871 0.515359 0.091 Uiso calc U . R 1.0 . .
H H19C 0.58126 0.354841 0.458306 0.091 Uiso calc U . R 1.0 . .
C C20 0.57577(18) 0.07651(14) 0.76043(16) 0.0327(5) Uani d U . . 1.0 . .
H H20 0.540432 0.111603 0.791132 0.039 Uiso calc U . R 1.0 . .
C C21 0.5046(2) 0.00764(16) 0.7159(2) 0.0461(7) Uani d U . . 1.0 . .
H H21A 0.443592 0.027606 0.666139 0.069 Uiso calc U . R 1.0 . .
H H21B 0.484905 -0.018885 0.763111 0.069 Uiso calc U . R 1.0 . .
H H21C 0.539728 -0.029995 0.689746 0.069 Uiso calc U . R 1.0 . .
C C22 0.6745(2) 0.04689(16) 0.83570(18) 0.0401(6) Uani d U . . 1.0 . .
H H22A 0.711082 0.012772 0.807175 0.06 Uiso calc U . R 1.0 . .
H H22B 0.658063 0.016864 0.882598 0.06 Uiso calc U . R 1.0 . .
H H22C 0.717513 0.092138 0.865398 0.06 Uiso calc U . R 1.0 . .
N N2 0.47182(14) 0.33062(11) 0.79954(13) 0.0296(4) Uani d . . . 1.0 . .
C C31 0.40494(17) 0.39073(14) 0.81373(15) 0.0293(5) Uani d U . . 1.0 . .
C C32 0.31286(18) 0.36715(14) 0.82084(15) 0.0314(5) Uani d U . . 1.0 . .
C C33 0.24925(19) 0.42699(16) 0.82988(16) 0.0355(6) Uani d U . . 1.0 . .
H H33 0.185475 0.413576 0.833567 0.043 Uiso calc U . R 1.0 . .
C C34 0.2775(2) 0.50571(16) 0.83358(18) 0.0427(6) Uani d U . . 1.0 . .
H H34 0.231803 0.545686 0.837205 0.051 Uiso calc U . R 1.0 . .
C C35 0.3713(2) 0.52643(16) 0.83203(19) 0.0434(6) Uani d U . . 1.0 . .
H H35 0.390742 0.580497 0.837553 0.052 Uiso calc U . R 1.0 . .
C C37 0.2875(2) 0.28128(16) 0.8272(2) 0.0449(7) Uani d U . . 1.0 . .
H H37 0.315313 0.249803 0.787096 0.054 Uiso calc U . R 1.0 . .
C C38 0.1740(2) 0.26355(19) 0.7976(2) 0.0544(8) Uani d U . . 1.0 . .
H H38A 0.164275 0.206795 0.803803 0.082 Uiso calc U . R 1.0 . .
H H38B 0.145957 0.292989 0.837322 0.082 Uiso calc U . R 1.0 . .
H H38C 0.138962 0.279456 0.732592 0.082 Uiso calc U . R 1.0 . .
C C39 0.3423(2) 0.25510(19) 0.9293(3) 0.0645(10) Uani d U . . 1.0 . .
H H39A 0.32721 0.199351 0.935648 0.097 Uiso calc U . R 1.0 . .
H H39B 0.415924 0.261991 0.947005 0.097 Uiso calc U . R 1.0 . .
H H39C 0.318396 0.287331 0.969918 0.097 Uiso calc U . R 1.0 . .
C C36 0.4384(2) 0.46944(14) 0.82249(17) 0.0357(6) Uani d U . . 1.0 . .
C C40 0.5453(2) 0.49368(16) 0.8295(2) 0.0428(6) Uani d U . . 1.0 . .
H H40 0.574093 0.450479 0.802325 0.051 Uiso calc U . R 1.0 . .
C C41 0.6128(2) 0.50320(17) 0.9318(2) 0.0496(7) Uani d U . . 1.0 . .
H H41A 0.584539 0.544378 0.959943 0.074 Uiso calc U . R 1.0 . .
H H41B 0.68168 0.518247 0.936849 0.074 Uiso calc U . R 1.0 . .
H H41C 0.615553 0.453089 0.964466 0.074 Uiso calc U . R 1.0 . .
C C42 0.5500(3) 0.5713(2) 0.7796(3) 0.0673(10) Uani d U . . 1.0 . .
H H42A 0.504632 0.56783 0.714112 0.101 Uiso calc U . R 1.0 . .
H H42B 0.61995 0.580526 0.78335 0.101 Uiso calc U . R 1.0 . .
H H42C 0.528333 0.615185 0.809459 0.101 Uiso calc U . R 1.0 . .
B B1 0.38374(19) 0.30501(16) 0.61082(17) 0.0269(5) Uani d . . D 1.0 . .
C C51 0.2867(2) 0.36231(19) 0.6006(2) 0.0254(7) Uani d U P D 0.871(3) A 1
C C52 0.1875(2) 0.33877(17) 0.58432(17) 0.0289(6) Uani d U P D 0.871(3) A 1
F F52 0.16170(13) 0.26140(14) 0.57398(12) 0.0362(5) Uani d U P D 0.871(3) A 1
C C53 0.1104(3) 0.3908(2) 0.5798(2) 0.0430(9) Uani d U P D 0.871(3) A 1
F F53 0.01683(14) 0.36391(14) 0.56824(13) 0.0571(6) Uani d U P D 0.871(3) A 1
C C54 0.1306(3) 0.4705(3) 0.5908(2) 0.0473(10) Uani d U P D 0.871(3) A 1
F F54 0.05770(18) 0.52197(13) 0.59079(13) 0.0680(7) Uani d U P D 0.871(3) A 1
C C55 0.2264(3) 0.49721(17) 0.60366(19) 0.0439(8) Uani d U P D 0.871(3) A 1
F F55 0.2472(2) 0.57498(10) 0.61343(14) 0.0661(7) Uani d U P D 0.871(3) A 1
C C56 0.2992(4) 0.4435(3) 0.6077(4) 0.0340(12) Uani d U P D 0.871(3) A 1
F F56 0.39462(18) 0.47358(10) 0.62349(12) 0.0432(5) Uani d U P D 0.871(3) A 1
C C51A 0.2648(11) 0.3329(10) 0.5998(17) 0.029(6) Uani d U P D 0.129(3) A 2
C C52A 0.1837(12) 0.2880(10) 0.6004(19) 0.036(6) Uani d U P D 0.129(3) A 2
F F52A 0.1880(9) 0.2074(8) 0.6103(9) 0.048(3) Uani d U P D 0.129(3) A 2
C C53A 0.0895(11) 0.3156(9) 0.5932(16) 0.049(6) Uani d U P D 0.129(3) A 2
F F53A 0.0135(9) 0.2688(11) 0.5961(10) 0.076(5) Uani d U P D 0.129(3) A 2
C C54A 0.0748(15) 0.3959(10) 0.586(2) 0.049(7) Uani d U P D 0.129(3) A 2
F F54A -0.0166(11) 0.4274(12) 0.5808(11) 0.088(6) Uani d U P D 0.129(3) A 2
C C55A 0.1512(15) 0.4462(11) 0.585(3) 0.060(8) Uani d U P D 0.129(3) A 2
F F55A 0.1394(16) 0.5250(11) 0.5810(12) 0.091(6) Uani d U P D 0.129(3) A 2
C C56A 0.2445(13) 0.4130(10) 0.5957(15) 0.038(5) Uani d U P D 0.129(3) A 2
F F56A 0.3198(17) 0.4619(12) 0.5955(16) 0.038(5) Uani d U P D 0.129(3) A 2
C C61 0.35427(17) 0.20878(14) 0.48642(16) 0.0291(5) Uani d U . . 1.0 . .
C C62 0.39233(18) 0.27630(15) 0.45779(16) 0.0325(5) Uani d U . . 1.0 . .
C C63 0.3873(2) 0.27912(19) 0.36641(18) 0.0465(7) Uani d U . . 1.0 . .
H H63 0.410914 0.324444 0.344115 0.056 Uiso calc U . R 1.0 . .
C C64 0.3471(2) 0.2146(2) 0.3071(2) 0.0582(9) Uani d U . . 1.0 . .
H H64 0.342359 0.216957 0.244158 0.07 Uiso calc U . R 1.0 . .
C C65 0.3144(2) 0.1481(2) 0.3392(2) 0.0561(8) Uani d U . . 1.0 . .
H H65 0.288959 0.104547 0.298411 0.067 Uiso calc U . R 1.0 . .
C C66 0.3180(2) 0.14351(16) 0.42914(19) 0.0431(6) Uani d U . . 1.0 . .
H H66 0.296367 0.097244 0.45148 0.052 Uiso calc U . R 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . 1.354(3) ?
N1 C2 . 1.389(3) ?
N1 C11 . 1.447(3) ?
N3 O1 . 1.289(2) ?
N3 C61 . 1.386(3) ?
N3 B1 . 1.563(3) ?
C1 N2 . 1.358(3) ?
C1 B1 . 1.633(3) ?
C2 C3 . 1.343(3) ?
C2 H2 . 0.95 ?
C3 N2 . 1.383(3) ?
C3 H3 . 0.95 ?
C11 C16 . 1.392(3) ?
C11 C12 . 1.406(3) ?
C12 C13 . 1.382(4) ?
C12 C17 . 1.518(4) ?
C13 C14 . 1.377(5) ?
C13 H13 . 0.95 ?
C14 C15 . 1.375(4) ?
C14 H14 . 0.95 ?
C15 C16 . 1.401(3) ?
C15 H15 . 0.95 ?
C16 C20 . 1.522(3) ?
C17 C19 . 1.530(4) ?
C17 C18 . 1.570(3) ?
C17 H17 . 1.0 ?
C18 C62 . 1.517(3) ?
C18 B1 . 1.649(3) ?
C18 H18 . 1.0 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C20 C21 . 1.528(4) ?
C20 C22 . 1.535(3) ?
C20 H20 . 1.0 ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
N2 C31 . 1.458(3) ?
C31 C32 . 1.402(3) ?
C31 C36 . 1.403(3) ?
C32 C33 . 1.394(3) ?
C32 C37 . 1.508(4) ?
C33 C34 . 1.386(4) ?
C33 H33 . 0.95 ?
C34 C35 . 1.379(4) ?
C34 H34 . 0.95 ?
C35 C36 . 1.397(4) ?
C35 H35 . 0.95 ?
C37 C38 . 1.525(4) ?
C37 C39 . 1.544(4) ?
C37 H37 . 1.0 ?
C38 H38A . 0.98 ?
C38 H38B . 0.98 ?
C38 H38C . 0.98 ?
C39 H39A . 0.98 ?
C39 H39B . 0.98 ?
C39 H39C . 0.98 ?
C36 C40 . 1.529(4) ?
C40 C41 . 1.526(4) ?
C40 C42 . 1.537(4) ?
C40 H40 . 1.0 ?
C41 H41A . 0.98 ?
C41 H41B . 0.98 ?
C41 H41C . 0.98 ?
C42 H42A . 0.98 ?
C42 H42B . 0.98 ?
C42 H42C . 0.98 ?
B1 C51 . 1.638(4) ?
B1 C51A . 1.691(14) ?
C51 C56 . 1.384(6) ?
C51 C52 . 1.387(4) ?
C52 F52 . 1.353(3) ?
C52 C53 . 1.381(4) ?
C53 F53 . 1.345(4) ?
C53 C54 . 1.376(5) ?
C54 F54 . 1.348(4) ?
C54 C55 . 1.368(5) ?
C55 F55 . 1.345(4) ?
C55 C56 . 1.356(6) ?
C56 F56 . 1.376(5) ?
C51A C52A . 1.377(13) ?
C51A C56A . 1.381(16) ?
C52A F52A . 1.372(14) ?
C52A C53A . 1.374(13) ?
C53A F53A . 1.348(13) ?
C53A C54A . 1.372(13) ?
C54A F54A . 1.373(13) ?
C54A C55A . 1.375(13) ?
C55A F55A . 1.343(13) ?
C55A C56A . 1.386(13) ?
C56A F56A . 1.348(13) ?
C61 C66 . 1.390(4) ?
C61 C62 . 1.401(3) ?
C62 C63 . 1.387(3) ?
C63 C64 . 1.404(5) ?
C63 H63 . 0.95 ?
C64 C65 . 1.376(5) ?
C64 H64 . 0.95 ?
C65 C66 . 1.374(4) ?
C65 H65 . 0.95 ?
C66 H66 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 110.48(18) ?
C1 N1 C11 . . 126.13(18) ?
C2 N1 C11 . . 123.22(18) ?
O1 N3 C61 . . 122.7(2) ?
O1 N3 B1 . . 126.17(19) ?
C61 N3 B1 . . 111.17(18) ?
N1 C1 N2 . . 105.25(18) ?
N1 C1 B1 . . 121.14(19) ?
N2 C1 B1 . . 133.6(2) ?
C3 C2 N1 . . 106.67(19) ?
C3 C2 H2 . . 126.7 ?
N1 C2 H2 . . 126.7 ?
C2 C3 N2 . . 107.4(2) ?
C2 C3 H3 . . 126.3 ?
N2 C3 H3 . . 126.3 ?
C16 C11 C12 . . 123.3(2) ?
C16 C11 N1 . . 119.4(2) ?
C12 C11 N1 . . 117.3(2) ?
C13 C12 C11 . . 117.1(3) ?
C13 C12 C17 . . 121.3(2) ?
C11 C12 C17 . . 121.4(2) ?
C14 C13 C12 . . 121.1(3) ?
C14 C13 H13 . . 119.4 ?
C12 C13 H13 . . 119.4 ?
C15 C14 C13 . . 120.7(3) ?
C15 C14 H14 . . 119.6 ?
C13 C14 H14 . . 119.6 ?
C14 C15 C16 . . 121.0(3) ?
C14 C15 H15 . . 119.5 ?
C16 C15 H15 . . 119.5 ?
C11 C16 C15 . . 116.7(2) ?
C11 C16 C20 . . 124.0(2) ?
C15 C16 C20 . . 119.2(2) ?
C12 C17 C19 . . 114.4(2) ?
C12 C17 C18 . . 108.3(2) ?
C19 C17 C18 . . 112.2(2) ?
C12 C17 H17 . . 107.2 ?
C19 C17 H17 . . 107.2 ?
C18 C17 H17 . . 107.2 ?
C62 C18 C17 . . 112.9(2) ?
C62 C18 B1 . . 101.81(18) ?
C17 C18 B1 . . 112.75(18) ?
C62 C18 H18 . . 109.7 ?
C17 C18 H18 . . 109.7 ?
B1 C18 H18 . . 109.7 ?
C17 C19 H19A . . 109.5 ?
C17 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C17 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C16 C20 C21 . . 110.5(2) ?
C16 C20 C22 . . 111.7(2) ?
C21 C20 C22 . . 110.9(2) ?
C16 C20 H20 . . 107.9 ?
C21 C20 H20 . . 107.9 ?
C22 C20 H20 . . 107.9 ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C20 C22 H22A . . 109.5 ?
C20 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C20 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C1 N2 C3 . . 110.16(19) ?
C1 N2 C31 . . 127.08(18) ?
C3 N2 C31 . . 122.64(18) ?
C32 C31 C36 . . 123.5(2) ?
C32 C31 N2 . . 118.9(2) ?
C36 C31 N2 . . 117.6(2) ?
C33 C32 C31 . . 116.8(2) ?
C33 C32 C37 . . 121.1(2) ?
C31 C32 C37 . . 121.9(2) ?
C34 C33 C32 . . 121.1(2) ?
C34 C33 H33 . . 119.4 ?
C32 C33 H33 . . 119.4 ?
C35 C34 C33 . . 120.5(2) ?
C35 C34 H34 . . 119.8 ?
C33 C34 H34 . . 119.8 ?
C34 C35 C36 . . 121.3(3) ?
C34 C35 H35 . . 119.4 ?
C36 C35 H35 . . 119.4 ?
C32 C37 C38 . . 114.7(2) ?
C32 C37 C39 . . 107.5(2) ?
C38 C37 C39 . . 109.1(2) ?
C32 C37 H37 . . 108.5 ?
C38 C37 H37 . . 108.5 ?
C39 C37 H37 . . 108.5 ?
C37 C38 H38A . . 109.5 ?
C37 C38 H38B . . 109.5 ?
H38A C38 H38B . . 109.5 ?
C37 C38 H38C . . 109.5 ?
H38A C38 H38C . . 109.5 ?
H38B C38 H38C . . 109.5 ?
C37 C39 H39A . . 109.5 ?
C37 C39 H39B . . 109.5 ?
H39A C39 H39B . . 109.5 ?
C37 C39 H39C . . 109.5 ?
H39A C39 H39C . . 109.5 ?
H39B C39 H39C . . 109.5 ?
C35 C36 C31 . . 116.7(2) ?
C35 C36 C40 . . 119.8(2) ?
C31 C36 C40 . . 123.4(2) ?
C41 C40 C36 . . 109.0(2) ?
C41 C40 C42 . . 107.7(2) ?
C36 C40 C42 . . 114.6(2) ?
C41 C40 H40 . . 108.4 ?
C36 C40 H40 . . 108.4 ?
C42 C40 H40 . . 108.4 ?
C40 C41 H41A . . 109.5 ?
C40 C41 H41B . . 109.5 ?
H41A C41 H41B . . 109.5 ?
C40 C41 H41C . . 109.5 ?
H41A C41 H41C . . 109.5 ?
H41B C41 H41C . . 109.5 ?
C40 C42 H42A . . 109.5 ?
C40 C42 H42B . . 109.5 ?
H42A C42 H42B . . 109.5 ?
C40 C42 H42C . . 109.5 ?
H42A C42 H42C . . 109.5 ?
H42B C42 H42C . . 109.5 ?
N3 B1 C1 . . 105.83(18) ?
N3 B1 C51 . . 115.3(2) ?
C1 B1 C51 . . 113.5(2) ?
N3 B1 C18 . . 99.78(18) ?
C1 B1 C18 . . 112.76(19) ?
C51 B1 C18 . . 108.9(2) ?
N3 B1 C51A . . 96.5(6) ?
C1 B1 C51A . . 115.6(9) ?
C18 B1 C51A . . 121.7(8) ?
C56 C51 C52 . . 113.0(3) ?
C56 C51 B1 . . 120.1(3) ?
C52 C51 B1 . . 126.9(3) ?
F52 C52 C53 . . 116.0(3) ?
F52 C52 C51 . . 120.6(2) ?
C53 C52 C51 . . 123.3(3) ?
F53 C53 C54 . . 119.8(3) ?
F53 C53 C52 . . 120.5(3) ?
C54 C53 C52 . . 119.7(3) ?
F54 C54 C55 . . 120.0(4) ?
F54 C54 C53 . . 120.6(4) ?
C55 C54 C53 . . 119.4(4) ?
F55 C55 C56 . . 121.3(4) ?
F55 C55 C54 . . 120.2(3) ?
C56 C55 C54 . . 118.4(4) ?
C55 C56 F56 . . 115.8(4) ?
C55 C56 C51 . . 126.1(5) ?
F56 C56 C51 . . 118.0(4) ?
C52A C51A C56A . . 112.5(13) ?
C52A C51A B1 . . 129.9(12) ?
C56A C51A B1 . . 117.4(11) ?
F52A C52A C53A . . 110.5(12) ?
F52A C52A C51A . . 123.1(13) ?
C53A C52A C51A . . 126.4(14) ?
F53A C53A C54A . . 119.2(13) ?
F53A C53A C52A . . 123.7(13) ?
C54A C53A C52A . . 117.0(13) ?
C53A C54A F54A . . 119.9(15) ?
C53A C54A C55A . . 121.3(13) ?
F54A C54A C55A . . 118.8(14) ?
F55A C55A C54A . . 122.2(16) ?
F55A C55A C56A . . 120.3(15) ?
C54A C55A C56A . . 117.4(15) ?
F56A C56A C51A . . 116.9(15) ?
F56A C56A C55A . . 117.8(17) ?
C51A C56A C55A . . 125.1(15) ?
N3 C61 C66 . . 126.5(2) ?
N3 C61 C62 . . 110.7(2) ?
C66 C61 C62 . . 122.8(2) ?
C63 C62 C61 . . 117.8(2) ?
C63 C62 C18 . . 130.6(2) ?
C61 C62 C18 . . 111.6(2) ?
C62 C63 C64 . . 119.7(3) ?
C62 C63 H63 . . 120.2 ?
C64 C63 H63 . . 120.2 ?
C65 C64 C63 . . 120.6(3) ?
C65 C64 H64 . . 119.7 ?
C63 C64 H64 . . 119.7 ?
C66 C65 C64 . . 121.2(3) ?
C66 C65 H65 . . 119.4 ?
C64 C65 H65 . . 119.4 ?
C65 C66 C61 . . 117.8(3) ?
C65 C66 H66 . . 121.1 ?
C61 C66 H66 . . 121.1 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 N2 . . . . 0.0(2) ?
C11 N1 C1 N2 . . . . -175.4(2) ?
C2 N1 C1 B1 . . . . -178.5(2) ?
C11 N1 C1 B1 . . . . 6.1(3) ?
C1 N1 C2 C3 . . . . 0.3(3) ?
C11 N1 C2 C3 . . . . 175.9(2) ?
N1 C2 C3 N2 . . . . -0.5(3) ?
C1 N1 C11 C16 . . . . -128.2(2) ?
C2 N1 C11 C16 . . . . 57.0(3) ?
C1 N1 C11 C12 . . . . 52.8(3) ?
C2 N1 C11 C12 . . . . -122.1(2) ?
C16 C11 C12 C13 . . . . -2.7(4) ?
N1 C11 C12 C13 . . . . 176.3(2) ?
C16 C11 C12 C17 . . . . 171.6(2) ?
N1 C11 C12 C17 . . . . -9.4(3) ?
C11 C12 C13 C14 . . . . 0.9(4) ?
C17 C12 C13 C14 . . . . -173.4(3) ?
C12 C13 C14 C15 . . . . 0.8(5) ?
C13 C14 C15 C16 . . . . -0.9(5) ?
C12 C11 C16 C15 . . . . 2.6(3) ?
N1 C11 C16 C15 . . . . -176.4(2) ?
C12 C11 C16 C20 . . . . -174.1(2) ?
N1 C11 C16 C20 . . . . 6.9(3) ?
C14 C15 C16 C11 . . . . -0.8(4) ?
C14 C15 C16 C20 . . . . 176.2(3) ?
C13 C12 C17 C19 . . . . -25.0(4) ?
C11 C12 C17 C19 . . . . 161.0(2) ?
C13 C12 C17 C18 . . . . 101.1(3) ?
C11 C12 C17 C18 . . . . -73.0(3) ?
C12 C17 C18 C62 . . . . -48.6(3) ?
C19 C17 C18 C62 . . . . 78.7(3) ?
C12 C17 C18 B1 . . . . 66.1(3) ?
C19 C17 C18 B1 . . . . -166.6(2) ?
C11 C16 C20 C21 . . . . 123.8(2) ?
C15 C16 C20 C21 . . . . -52.9(3) ?
C11 C16 C20 C22 . . . . -112.3(3) ?
C15 C16 C20 C22 . . . . 71.0(3) ?
N1 C1 N2 C3 . . . . -0.3(3) ?
B1 C1 N2 C3 . . . . 177.9(2) ?
N1 C1 N2 C31 . . . . 175.9(2) ?
B1 C1 N2 C31 . . . . -5.9(4) ?
C2 C3 N2 C1 . . . . 0.5(3) ?
C2 C3 N2 C31 . . . . -175.9(2) ?
C1 N2 C31 C32 . . . . 83.8(3) ?
C3 N2 C31 C32 . . . . -100.5(3) ?
C1 N2 C31 C36 . . . . -98.2(3) ?
C3 N2 C31 C36 . . . . 77.6(3) ?
C36 C31 C32 C33 . . . . 5.1(3) ?
N2 C31 C32 C33 . . . . -177.01(19) ?
C36 C31 C32 C37 . . . . -169.5(2) ?
N2 C31 C32 C37 . . . . 8.4(3) ?
C31 C32 C33 C34 . . . . -1.3(3) ?
C37 C32 C33 C34 . . . . 173.3(2) ?
C32 C33 C34 C35 . . . . -2.6(4) ?
C33 C34 C35 C36 . . . . 2.9(4) ?
C33 C32 C37 C38 . . . . 28.0(4) ?
C31 C32 C37 C38 . . . . -157.6(2) ?
C33 C32 C37 C39 . . . . -93.5(3) ?
C31 C32 C37 C39 . . . . 80.9(3) ?
C34 C35 C36 C31 . . . . 0.6(4) ?
C34 C35 C36 C40 . . . . -174.7(2) ?
C32 C31 C36 C35 . . . . -4.7(3) ?
N2 C31 C36 C35 . . . . 177.3(2) ?
C32 C31 C36 C40 . . . . 170.4(2) ?
N2 C31 C36 C40 . . . . -7.5(3) ?
C35 C36 C40 C41 . . . . 79.1(3) ?
C31 C36 C40 C41 . . . . -95.9(3) ?
C35 C36 C40 C42 . . . . -41.6(4) ?
C31 C36 C40 C42 . . . . 143.3(3) ?
O1 N3 B1 C1 . . . . 44.5(3) ?
C61 N3 B1 C1 . . . . -136.00(18) ?
O1 N3 B1 C51 . . . . -81.8(3) ?
C61 N3 B1 C51 . . . . 97.6(2) ?
O1 N3 B1 C18 . . . . 161.72(19) ?
C61 N3 B1 C18 . . . . -18.8(2) ?
O1 N3 B1 C51A . . . . -74.5(9) ?
C61 N3 B1 C51A . . . . 105.0(8) ?
N1 C1 B1 N3 . . . . 49.1(3) ?
N2 C1 B1 N3 . . . . -128.8(3) ?
N1 C1 B1 C51 . . . . 176.5(2) ?
N2 C1 B1 C51 . . . . -1.4(4) ?
N1 C1 B1 C18 . . . . -59.0(3) ?
N2 C1 B1 C18 . . . . 123.1(3) ?
N1 C1 B1 C51A . . . . 154.5(6) ?
N2 C1 B1 C51A . . . . -23.4(7) ?
C62 C18 B1 N3 . . . . 21.0(2) ?
C17 C18 B1 N3 . . . . -100.3(2) ?
C62 C18 B1 C1 . . . . 132.9(2) ?
C17 C18 B1 C1 . . . . 11.6(3) ?
C62 C18 B1 C51 . . . . -100.1(2) ?
C17 C18 B1 C51 . . . . 138.6(2) ?
C62 C18 B1 C51A . . . . -82.9(8) ?
C17 C18 B1 C51A . . . . 155.8(8) ?
N3 B1 C51 C56 . . . . -164.5(3) ?
C1 B1 C51 C56 . . . . 73.2(4) ?
C18 B1 C51 C56 . . . . -53.4(4) ?
N3 B1 C51 C52 . . . . 15.0(4) ?
C1 B1 C51 C52 . . . . -107.3(3) ?
C18 B1 C51 C52 . . . . 126.2(3) ?
C56 C51 C52 F52 . . . . 178.9(3) ?
B1 C51 C52 F52 . . . . -0.7(4) ?
C56 C51 C52 C53 . . . . -2.7(5) ?
B1 C51 C52 C53 . . . . 177.7(3) ?
F52 C52 C53 F53 . . . . 1.7(4) ?
C51 C52 C53 F53 . . . . -176.8(3) ?
F52 C52 C53 C54 . . . . 179.2(3) ?
C51 C52 C53 C54 . . . . 0.8(5) ?
F53 C53 C54 F54 . . . . 0.6(5) ?
C52 C53 C54 F54 . . . . -177.0(3) ?
F53 C53 C54 C55 . . . . 179.2(3) ?
C52 C53 C54 C55 . . . . 1.6(5) ?
F54 C54 C55 F55 . . . . -2.1(5) ?
C53 C54 C55 F55 . . . . 179.2(3) ?
F54 C54 C55 C56 . . . . 176.9(3) ?
C53 C54 C55 C56 . . . . -1.8(5) ?
F55 C55 C56 F56 . . . . 0.8(6) ?
C54 C55 C56 F56 . . . . -178.2(3) ?
F55 C55 C56 C51 . . . . 178.5(4) ?
C54 C55 C56 C51 . . . . -0.5(7) ?
C52 C51 C56 C55 . . . . 2.6(6) ?
B1 C51 C56 C55 . . . . -177.7(4) ?
C52 C51 C56 F56 . . . . -179.7(3) ?
B1 C51 C56 F56 . . . . -0.1(6) ?
N3 B1 C51A C52A . . . . 24.(3) ?
C1 B1 C51A C52A . . . . -87.(3) ?
C18 B1 C51A C52A . . . . 130.(2) ?
N3 B1 C51A C56A . . . . -160.5(19) ?
C1 B1 C51A C56A . . . . 88.(2) ?
C18 B1 C51A C56A . . . . -55.(2) ?
C56A C51A C52A F52A . . . . -176.(2) ?
B1 C51A C52A F52A . . . . 0.(4) ?
C56A C51A C52A C53A . . . . 3.(4) ?
B1 C51A C52A C53A . . . . 178.(2) ?
F52A C52A C53A F53A . . . . 0.(3) ?
C51A C52A C53A F53A . . . . -179.(2) ?
F52A C52A C53A C54A . . . . 178.(2) ?
C51A C52A C53A C54A . . . . -1.(4) ?
F53A C53A C54A F54A . . . . 0.(4) ?
C52A C53A C54A F54A . . . . -178.(2) ?
F53A C53A C54A C55A . . . . 178.(3) ?
C52A C53A C54A C55A . . . . 0.(5) ?
C53A C54A C55A F55A . . . . -178.(3) ?
F54A C54A C55A F55A . . . . 0.(5) ?
C53A C54A C55A C56A . . . . -2.(5) ?
F54A C54A C55A C56A . . . . 176.(3) ?
C52A C51A C56A F56A . . . . 180.(2) ?
B1 C51A C56A F56A . . . . 4.(3) ?
C52A C51A C56A C55A . . . . -5.(4) ?
B1 C51A C56A C55A . . . . 179.(2) ?
F55A C55A C56A F56A . . . . -4.(5) ?
C54A C55A C56A F56A . . . . 180.(3) ?
F55A C55A C56A C51A . . . . -179.(3) ?
C54A C55A C56A C51A . . . . 5.(5) ?
O1 N3 C61 C66 . . . . 9.8(3) ?
B1 N3 C61 C66 . . . . -169.7(2) ?
O1 N3 C61 C62 . . . . -171.96(19) ?
B1 N3 C61 C62 . . . . 8.5(2) ?
N3 C61 C62 C63 . . . . -174.3(2) ?
C66 C61 C62 C63 . . . . 4.0(4) ?
N3 C61 C62 C18 . . . . 7.3(3) ?
C66 C61 C62 C18 . . . . -174.4(2) ?
C17 C18 C62 C63 . . . . -75.5(3) ?
B1 C18 C62 C63 . . . . 163.3(3) ?
C17 C18 C62 C61 . . . . 102.6(2) ?
B1 C18 C62 C61 . . . . -18.5(2) ?
C61 C62 C63 C64 . . . . -1.4(4) ?
C18 C62 C63 C64 . . . . 176.6(2) ?
C62 C63 C64 C65 . . . . -1.2(4) ?
C63 C64 C65 C66 . . . . 1.5(5) ?
C64 C65 C66 C61 . . . . 0.9(4) ?
N3 C61 C66 C65 . . . . 174.2(2) ?
C62 C61 C66 C65 . . . . -3.8(4) ?


####################################################################### 
# 
# 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_5_erk9943
_database_code_depnum_ccdc_archive 'CCDC 2157863'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2022-03-11 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2019.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H38 B F5 N3 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         670.53

_chemical_melting_point          ?

_space_group_crystal_system      tetragonal
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   23.5399(8)
_cell_length_b                   23.5399(8)
_cell_length_c                   24.9570(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     13829.3(11)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9952
_cell_measurement_theta_min      2.4472
_cell_measurement_theta_max      26.6999
_cell_measurement_temperature    102.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.243
_exptl_crystal_size_min          0.192
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             5616

_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 Bruker AXS area detector scaling and absorption correction.
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      102.(2)

_diffrn_source                   'Mo Ims'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON III Diffractometer'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            162403
_diffrn_reflns_av_R_equivalents  0.0931
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         26.75
_diffrn_reflns_theta_full        26.75
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31

_refine_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_number_total             7357
_reflns_number_gt                6063
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0995
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_number_reflns         7357
_refine_ls_number_parameters     449
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0369P)²+16.7859P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.197
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
N N 0.0061 0.0033 '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'

_computing_data_collection       'APEX3 v2019.1-0'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.78127(7) 0.31049(7) 0.48516(6) 0.0180(3) Uani d . . . 1 . .
C C1 0.78482(6) 0.34749(6) 0.43001(6) 0.0165(3) Uani d . . . 1 . .
N N1 0.77379(5) 0.32221(5) 0.38225(5) 0.0173(2) Uani d . . . 1 . .
O O1 0.75525(5) 0.39376(5) 0.53672(4) 0.0247(2) Uani d . . . 1 . .
C C2 0.79263(6) 0.35623(6) 0.34040(6) 0.0210(3) Uani d . . . 1 . .
H H2 0.79028 0.3477 0.303263 0.025 Uiso calc U . R 1 . .
N N2 0.80958(5) 0.39783(5) 0.41767(5) 0.0176(2) Uani d . . . 1 . .
C C3 0.81482(6) 0.40342(7) 0.36224(6) 0.0207(3) Uani d . . . 1 . .
H H3 0.830973 0.434633 0.343524 0.025 Uiso calc U . R 1 . .
N N3 0.78939(5) 0.35019(5) 0.53451(5) 0.0196(3) Uani d . . . 1 . .
C C11 0.75198(6) 0.26535(6) 0.37596(6) 0.0179(3) Uani d . . . 1 . .
C C12 0.78209(6) 0.22023(6) 0.39982(6) 0.0199(3) Uani d . . . 1 . .
C C13 0.76127(7) 0.16536(6) 0.39185(6) 0.0247(3) Uani d . . . 1 . .
H H13 0.780978 0.134025 0.407014 0.03 Uiso calc U . R 1 . .
C C14 0.71247(7) 0.15571(7) 0.36226(7) 0.0271(3) Uani d . . . 1 . .
H H14 0.69853 0.118124 0.357882 0.033 Uiso calc U . R 1 . .
C C15 0.68401(7) 0.20093(7) 0.33906(6) 0.0243(3) Uani d . . . 1 . .
H H15 0.650874 0.193767 0.318406 0.029 Uiso calc U . R 1 . .
C C16 0.70277(6) 0.25667(6) 0.34528(6) 0.0198(3) Uani d . . . 1 . .
C C17 0.83344(6) 0.22903(7) 0.43377(6) 0.0220(3) Uani d . . . 1 . .
C C18 0.83308(6) 0.26725(6) 0.47353(6) 0.0203(3) Uani d . . . 1 . .
H H18 0.865355 0.269038 0.496324 0.024 Uiso calc U . R 1 . .
C C19 0.88340(7) 0.19074(8) 0.42211(7) 0.0325(4) Uani d . . . 1 . .
H H19A 0.915689 0.201949 0.444527 0.049 Uiso calc U . R 1 . .
H H19B 0.893874 0.194118 0.384245 0.049 Uiso calc U . R 1 . .
H H19C 0.873046 0.15129 0.430006 0.049 Uiso calc U . R 1 . .
C C20 0.66930(6) 0.30473(6) 0.31907(6) 0.0226(3) Uani d . . . 1 . .
H H20 0.686738 0.341585 0.33033 0.027 Uiso calc U . R 1 . .
C C21 0.67349(7) 0.30040(7) 0.25762(6) 0.0281(4) Uani d . . . 1 . .
H H21A 0.713536 0.300641 0.246884 0.042 Uiso calc U . R 1 . .
H H21B 0.653936 0.332797 0.241251 0.042 Uiso calc U . R 1 . .
H H21C 0.655664 0.264993 0.245611 0.042 Uiso calc U . R 1 . .
C C22 0.60701(7) 0.30458(7) 0.33729(7) 0.0283(4) Uani d . . . 1 . .
H H22A 0.588058 0.270476 0.323584 0.042 Uiso calc U . R 1 . .
H H22B 0.587824 0.338459 0.323378 0.042 Uiso calc U . R 1 . .
H H22C 0.605371 0.304708 0.376524 0.042 Uiso calc U . R 1 . .
C C31 0.83579(6) 0.43903(6) 0.45354(6) 0.0195(3) Uani d . . . 1 . .
C C32 0.89328(6) 0.43116(7) 0.46602(6) 0.0232(3) Uani d . . . 1 . .
C C33 0.91897(7) 0.47254(8) 0.49807(7) 0.0308(4) Uani d . . . 1 . .
H H33 0.957673 0.468265 0.508091 0.037 Uiso calc U . R 1 . .
C C34 0.88915(8) 0.51935(8) 0.51534(7) 0.0352(4) Uani d . . . 1 . .
H H34 0.90752 0.547155 0.536812 0.042 Uiso calc U . R 1 . .
C C35 0.83256(8) 0.52623(7) 0.50167(7) 0.0304(4) Uani d . . . 1 . .
H H35 0.812676 0.558933 0.513735 0.036 Uiso calc U . R 1 . .
C C36 0.80415(7) 0.48597(7) 0.47047(6) 0.0227(3) Uani d . . . 1 . .
C C37 0.92783(6) 0.38204(8) 0.44399(6) 0.0266(3) Uani d . . . 1 . .
H H37 0.900767 0.353396 0.429015 0.032 Uiso calc U . R 1 . .
C C38 0.96352(7) 0.35264(9) 0.48721(7) 0.0345(4) Uani d . . . 1 . .
H H38A 0.993958 0.3782 0.498904 0.052 Uiso calc U . R 1 . .
H H38B 0.980147 0.317801 0.472508 0.052 Uiso calc U . R 1 . .
H H38C 0.939291 0.343132 0.517851 0.052 Uiso calc U . R 1 . .
C C39 0.96614(8) 0.40250(10) 0.39818(7) 0.0422(5) Uani d . . . 1 . .
H H39A 0.942626 0.418159 0.369343 0.063 Uiso calc U . R 1 . .
H H39B 0.988348 0.370449 0.384408 0.063 Uiso calc U . R 1 . .
H H39C 0.99194 0.431952 0.411521 0.063 Uiso calc U . R 1 . .
C C40 0.74243(7) 0.49430(7) 0.45470(7) 0.0258(3) Uani d . . . 1 . .
H H40 0.726032 0.456141 0.446289 0.031 Uiso calc U . R 1 . .
C C41 0.70698(8) 0.52065(8) 0.49957(7) 0.0357(4) Uani d . . . 1 . .
H H41A 0.712756 0.49912 0.532733 0.054 Uiso calc U . R 1 . .
H H41B 0.666707 0.519577 0.489687 0.054 Uiso calc U . R 1 . .
H H41C 0.718758 0.560156 0.505066 0.054 Uiso calc U . R 1 . .
C C42 0.73758(7) 0.53109(8) 0.40439(7) 0.0310(4) Uani d . . . 1 . .
H H42A 0.754012 0.568608 0.411447 0.047 Uiso calc U . R 1 . .
H H42B 0.697479 0.535321 0.394633 0.047 Uiso calc U . R 1 . .
H H42C 0.75815 0.512927 0.374863 0.047 Uiso calc U . R 1 . .
C C51 0.71851(6) 0.28050(6) 0.49391(5) 0.0178(3) Uani d . . . 1 . .
C C52 0.66741(6) 0.30790(6) 0.48311(6) 0.0207(3) Uani d . . . 1 . .
F F52 0.66720(4) 0.35830(4) 0.45679(4) 0.0282(2) Uani d . . . 1 . .
C C53 0.61472(6) 0.28664(7) 0.49706(6) 0.0224(3) Uani d . . . 1 . .
F F53 0.56691(4) 0.31597(4) 0.48638(4) 0.0345(2) Uani d . . . 1 . .
C C54 0.61072(6) 0.23503(7) 0.52273(6) 0.0211(3) Uani d . . . 1 . .
F F54 0.55993(4) 0.21455(4) 0.53763(4) 0.0287(2) Uani d . . . 1 . .
C C55 0.65982(7) 0.20559(6) 0.53383(6) 0.0203(3) Uani d . . . 1 . .
F F55 0.65698(4) 0.15569(4) 0.56009(4) 0.0290(2) Uani d . . . 1 . .
C C56 0.71165(6) 0.22857(6) 0.51935(6) 0.0191(3) Uani d . . . 1 . .
F F56 0.75737(4) 0.19677(4) 0.53312(4) 0.0267(2) Uani d . . . 1 . .
C C61 0.82748(6) 0.34391(7) 0.57776(6) 0.0214(3) Uani d . . . 1 . .
C C62 0.84802(7) 0.39255(7) 0.60307(6) 0.0268(3) Uani d . . . 1 . .
H H62 0.8373 0.429129 0.590574 0.032 Uiso calc U . R 1 . .
C C63 0.88411(8) 0.38716(8) 0.64649(7) 0.0347(4) Uani d . . . 1 . .
H H63 0.897853 0.420261 0.663984 0.042 Uiso calc U . R 1 . .
C C64 0.90044(8) 0.33419(9) 0.66474(7) 0.0374(4) Uani d . . . 1 . .
H H64 0.925155 0.330908 0.69467 0.045 Uiso calc U . R 1 . .
C C65 0.88061(8) 0.28600(8) 0.63920(7) 0.0354(4) Uani d . . . 1 . .
H H65 0.892235 0.249569 0.651363 0.043 Uiso calc U . R 1 . .
C C66 0.84382(7) 0.29044(7) 0.59589(6) 0.0271(3) Uani d . . . 1 . .
H H66 0.8299 0.257195 0.578756 0.032 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 N3 . 1.558(2) ?
B1 C18 . 1.615(2) ?
B1 C1 . 1.631(2) ?
B1 C51 . 1.652(2) ?
C1 N2 . 1.3561(18) ?
C1 N1 . 1.3574(18) ?
N1 C2 . 1.3887(19) ?
N1 C11 . 1.4421(18) ?
O1 N3 . 1.3043(16) ?
C2 C3 . 1.343(2) ?
C2 H2 . 0.95 ?
N2 C3 . 1.3952(18) ?
N2 C31 . 1.4570(18) ?
C3 H3 . 0.95 ?
N3 C61 . 1.4109(19) ?
C11 C16 . 1.404(2) ?
C11 C12 . 1.409(2) ?
C12 C13 . 1.396(2) ?
C12 C17 . 1.491(2) ?
C13 C14 . 1.384(2) ?
C13 H13 . 0.95 ?
C14 C15 . 1.385(2) ?
C14 H14 . 0.95 ?
C15 C16 . 1.393(2) ?
C15 H15 . 0.95 ?
C16 C20 . 1.526(2) ?
C17 C18 . 1.339(2) ?
C17 C19 . 1.510(2) ?
C18 H18 . 0.95 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C20 C22 . 1.535(2) ?
C20 C21 . 1.540(2) ?
C20 H20 . 1.0 ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
C31 C36 . 1.398(2) ?
C31 C32 . 1.401(2) ?
C32 C33 . 1.398(2) ?
C32 C37 . 1.517(2) ?
C33 C34 . 1.376(3) ?
C33 H33 . 0.95 ?
C34 C35 . 1.385(2) ?
C34 H34 . 0.95 ?
C35 C36 . 1.397(2) ?
C35 H35 . 0.95 ?
C36 C40 . 1.518(2) ?
C37 C38 . 1.532(2) ?
C37 C39 . 1.534(2) ?
C37 H37 . 1.0 ?
C38 H38A . 0.98 ?
C38 H38B . 0.98 ?
C38 H38C . 0.98 ?
C39 H39A . 0.98 ?
C39 H39B . 0.98 ?
C39 H39C . 0.98 ?
C40 C41 . 1.528(2) ?
C40 C42 . 1.529(2) ?
C40 H40 . 1.0 ?
C41 H41A . 0.98 ?
C41 H41B . 0.98 ?
C41 H41C . 0.98 ?
C42 H42A . 0.98 ?
C42 H42B . 0.98 ?
C42 H42C . 0.98 ?
C51 C56 . 1.387(2) ?
C51 C52 . 1.391(2) ?
C52 F52 . 1.3560(17) ?
C52 C53 . 1.382(2) ?
C53 F53 . 1.3470(17) ?
C53 C54 . 1.377(2) ?
C54 F54 . 1.3417(17) ?
C54 C55 . 1.376(2) ?
C55 F55 . 1.3467(17) ?
C55 C56 . 1.383(2) ?
C56 F56 . 1.3550(16) ?
C61 C66 . 1.392(2) ?
C61 C62 . 1.394(2) ?
C62 C63 . 1.383(2) ?
C62 H62 . 0.95 ?
C63 C64 . 1.382(3) ?
C63 H63 . 0.95 ?
C64 C65 . 1.382(3) ?
C64 H64 . 0.95 ?
C65 C66 . 1.389(2) ?
C65 H65 . 0.95 ?
C66 H66 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 B1 C18 . . 115.31(12) ?
N3 B1 C1 . . 109.91(12) ?
C18 B1 C1 . . 98.40(11) ?
N3 B1 C51 . . 105.17(12) ?
C18 B1 C51 . . 115.47(12) ?
C1 B1 C51 . . 112.68(11) ?
N2 C1 N1 . . 105.41(12) ?
N2 C1 B1 . . 132.87(12) ?
N1 C1 B1 . . 119.82(12) ?
C1 N1 C2 . . 110.28(12) ?
C1 N1 C11 . . 124.78(12) ?
C2 N1 C11 . . 124.54(12) ?
C3 C2 N1 . . 107.22(13) ?
C3 C2 H2 . . 126.4 ?
N1 C2 H2 . . 126.4 ?
C1 N2 C3 . . 110.22(12) ?
C1 N2 C31 . . 128.62(12) ?
C3 N2 C31 . . 120.60(12) ?
C2 C3 N2 . . 106.85(13) ?
C2 C3 H3 . . 126.6 ?
N2 C3 H3 . . 126.6 ?
O1 N3 C61 . . 116.20(12) ?
O1 N3 B1 . . 115.44(11) ?
C61 N3 B1 . . 128.31(12) ?
C16 C11 C12 . . 122.40(13) ?
C16 C11 N1 . . 119.23(12) ?
C12 C11 N1 . . 118.34(13) ?
C13 C12 C11 . . 117.44(13) ?
C13 C12 C17 . . 119.63(13) ?
C11 C12 C17 . . 122.91(13) ?
C14 C13 C12 . . 121.28(14) ?
C14 C13 H13 . . 119.4 ?
C12 C13 H13 . . 119.4 ?
C13 C14 C15 . . 119.90(15) ?
C13 C14 H14 . . 120.1 ?
C15 C14 H14 . . 120.1 ?
C14 C15 C16 . . 121.61(14) ?
C14 C15 H15 . . 119.2 ?
C16 C15 H15 . . 119.2 ?
C15 C16 C11 . . 117.36(13) ?
C15 C16 C20 . . 119.14(13) ?
C11 C16 C20 . . 123.50(13) ?
C18 C17 C12 . . 120.62(13) ?
C18 C17 C19 . . 123.27(14) ?
C12 C17 C19 . . 116.04(13) ?
C17 C18 B1 . . 124.15(13) ?
C17 C18 H18 . . 117.9 ?
B1 C18 H18 . . 117.9 ?
C17 C19 H19A . . 109.5 ?
C17 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C17 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C16 C20 C22 . . 111.38(13) ?
C16 C20 C21 . . 110.16(13) ?
C22 C20 C21 . . 110.84(13) ?
C16 C20 H20 . . 108.1 ?
C22 C20 H20 . . 108.1 ?
C21 C20 H20 . . 108.1 ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C20 C22 H22A . . 109.5 ?
C20 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C20 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C36 C31 C32 . . 123.50(14) ?
C36 C31 N2 . . 119.10(13) ?
C32 C31 N2 . . 117.23(13) ?
C33 C32 C31 . . 116.94(15) ?
C33 C32 C37 . . 120.44(14) ?
C31 C32 C37 . . 122.55(14) ?
C34 C33 C32 . . 121.10(16) ?
C34 C33 H33 . . 119.5 ?
C32 C33 H33 . . 119.5 ?
C33 C34 C35 . . 120.49(15) ?
C33 C34 H34 . . 119.8 ?
C35 C34 H34 . . 119.8 ?
C34 C35 C36 . . 121.23(16) ?
C34 C35 H35 . . 119.4 ?
C36 C35 H35 . . 119.4 ?
C35 C36 C31 . . 116.72(15) ?
C35 C36 C40 . . 121.00(15) ?
C31 C36 C40 . . 122.26(14) ?
C32 C37 C38 . . 112.51(13) ?
C32 C37 C39 . . 110.25(15) ?
C38 C37 C39 . . 110.12(14) ?
C32 C37 H37 . . 107.9 ?
C38 C37 H37 . . 107.9 ?
C39 C37 H37 . . 107.9 ?
C37 C38 H38A . . 109.5 ?
C37 C38 H38B . . 109.5 ?
H38A C38 H38B . . 109.5 ?
C37 C38 H38C . . 109.5 ?
H38A C38 H38C . . 109.5 ?
H38B C38 H38C . . 109.5 ?
C37 C39 H39A . . 109.5 ?
C37 C39 H39B . . 109.5 ?
H39A C39 H39B . . 109.5 ?
C37 C39 H39C . . 109.5 ?
H39A C39 H39C . . 109.5 ?
H39B C39 H39C . . 109.5 ?
C36 C40 C41 . . 112.64(14) ?
C36 C40 C42 . . 110.94(13) ?
C41 C40 C42 . . 109.33(14) ?
C36 C40 H40 . . 107.9 ?
C41 C40 H40 . . 107.9 ?
C42 C40 H40 . . 107.9 ?
C40 C41 H41A . . 109.5 ?
C40 C41 H41B . . 109.5 ?
H41A C41 H41B . . 109.5 ?
C40 C41 H41C . . 109.5 ?
H41A C41 H41C . . 109.5 ?
H41B C41 H41C . . 109.5 ?
C40 C42 H42A . . 109.5 ?
C40 C42 H42B . . 109.5 ?
H42A C42 H42B . . 109.5 ?
C40 C42 H42C . . 109.5 ?
H42A C42 H42C . . 109.5 ?
H42B C42 H42C . . 109.5 ?
C56 C51 C52 . . 113.38(13) ?
C56 C51 B1 . . 122.76(13) ?
C52 C51 B1 . . 123.34(13) ?
F52 C52 C53 . . 115.82(13) ?
F52 C52 C51 . . 120.17(13) ?
C53 C52 C51 . . 124.00(14) ?
F53 C53 C54 . . 119.18(13) ?
F53 C53 C52 . . 120.94(13) ?
C54 C53 C52 . . 119.88(14) ?
F54 C54 C55 . . 120.79(13) ?
F54 C54 C53 . . 120.46(13) ?
C55 C54 C53 . . 118.74(14) ?
F55 C55 C54 . . 119.70(13) ?
F55 C55 C56 . . 120.81(13) ?
C54 C55 C56 . . 119.46(13) ?
F56 C56 C55 . . 114.74(13) ?
F56 C56 C51 . . 120.70(13) ?
C55 C56 C51 . . 124.54(13) ?
C66 C61 C62 . . 119.97(14) ?
C66 C61 N3 . . 121.27(14) ?
C62 C61 N3 . . 118.75(14) ?
C63 C62 C61 . . 119.53(16) ?
C63 C62 H62 . . 120.2 ?
C61 C62 H62 . . 120.2 ?
C64 C63 C62 . . 120.79(16) ?
C64 C63 H63 . . 119.6 ?
C62 C63 H63 . . 119.6 ?
C63 C64 C65 . . 119.64(16) ?
C63 C64 H64 . . 120.2 ?
C65 C64 H64 . . 120.2 ?
C64 C65 C66 . . 120.51(17) ?
C64 C65 H65 . . 119.7 ?
C66 C65 H65 . . 119.7 ?
C65 C66 C61 . . 119.56(15) ?
C65 C66 H66 . . 120.2 ?
C61 C66 H66 . . 120.2 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N3 B1 C1 N2 . . . . 24.1(2) ?
C18 B1 C1 N2 . . . . -96.80(17) ?
C51 B1 C1 N2 . . . . 141.00(15) ?
N3 B1 C1 N1 . . . . -174.10(12) ?
C18 B1 C1 N1 . . . . 65.03(15) ?
C51 B1 C1 N1 . . . . -57.16(17) ?
N2 C1 N1 C2 . . . . 1.17(15) ?
B1 C1 N1 C2 . . . . -165.12(12) ?
N2 C1 N1 C11 . . . . 174.22(12) ?
B1 C1 N1 C11 . . . . 7.9(2) ?
C1 N1 C2 C3 . . . . -0.90(17) ?
C11 N1 C2 C3 . . . . -173.97(13) ?
N1 C1 N2 C3 . . . . -1.01(15) ?
B1 C1 N2 C3 . . . . 162.70(15) ?
N1 C1 N2 C31 . . . . -172.38(13) ?
B1 C1 N2 C31 . . . . -8.7(2) ?
N1 C2 C3 N2 . . . . 0.25(17) ?
C1 N2 C3 C2 . . . . 0.48(17) ?
C31 N2 C3 C2 . . . . 172.65(13) ?
C18 B1 N3 O1 . . . . 164.08(12) ?
C1 B1 N3 O1 . . . . 54.01(16) ?
C51 B1 N3 O1 . . . . -67.53(15) ?
C18 B1 N3 C61 . . . . -18.3(2) ?
C1 B1 N3 C61 . . . . -128.37(15) ?
C51 B1 N3 C61 . . . . 110.10(15) ?
C1 N1 C11 C16 . . . . 126.10(15) ?
C2 N1 C11 C16 . . . . -61.83(19) ?
C1 N1 C11 C12 . . . . -55.65(19) ?
C2 N1 C11 C12 . . . . 116.42(16) ?
C16 C11 C12 C13 . . . . 0.2(2) ?
N1 C11 C12 C13 . . . . -178.03(13) ?
C16 C11 C12 C17 . . . . -178.20(14) ?
N1 C11 C12 C17 . . . . 3.6(2) ?
C11 C12 C13 C14 . . . . -0.9(2) ?
C17 C12 C13 C14 . . . . 177.53(15) ?
C12 C13 C14 C15 . . . . 1.3(2) ?
C13 C14 C15 C16 . . . . -0.9(3) ?
C14 C15 C16 C11 . . . . 0.2(2) ?
C14 C15 C16 C20 . . . . -179.53(15) ?
C12 C11 C16 C15 . . . . 0.2(2) ?
N1 C11 C16 C15 . . . . 178.35(13) ?
C12 C11 C16 C20 . . . . 179.90(14) ?
N1 C11 C16 C20 . . . . -1.9(2) ?
C13 C12 C17 C18 . . . . -129.25(16) ?
C11 C12 C17 C18 . . . . 49.1(2) ?
C13 C12 C17 C19 . . . . 47.9(2) ?
C11 C12 C17 C19 . . . . -133.77(16) ?
C12 C17 C18 B1 . . . . -5.8(2) ?
C19 C17 C18 B1 . . . . 177.25(15) ?
N3 B1 C18 C17 . . . . 178.43(14) ?
C1 B1 C18 C17 . . . . -64.79(18) ?
C51 B1 C18 C17 . . . . 55.3(2) ?
C15 C16 C20 C22 . . . . 56.45(19) ?
C11 C16 C20 C22 . . . . -123.27(15) ?
C15 C16 C20 C21 . . . . -66.97(18) ?
C11 C16 C20 C21 . . . . 113.31(16) ?
C1 N2 C31 C36 . . . . -97.54(18) ?
C3 N2 C31 C36 . . . . 91.87(17) ?
C1 N2 C31 C32 . . . . 86.99(18) ?
C3 N2 C31 C32 . . . . -83.59(17) ?
C36 C31 C32 C33 . . . . 1.3(2) ?
N2 C31 C32 C33 . . . . 176.59(13) ?
C36 C31 C32 C37 . . . . -175.59(14) ?
N2 C31 C32 C37 . . . . -0.3(2) ?
C31 C32 C33 C34 . . . . -1.4(2) ?
C37 C32 C33 C34 . . . . 175.55(16) ?
C32 C33 C34 C35 . . . . 0.6(3) ?
C33 C34 C35 C36 . . . . 0.4(3) ?
C34 C35 C36 C31 . . . . -0.5(2) ?
C34 C35 C36 C40 . . . . -178.79(16) ?
C32 C31 C36 C35 . . . . -0.4(2) ?
N2 C31 C36 C35 . . . . -175.53(14) ?
C32 C31 C36 C40 . . . . 177.86(14) ?
N2 C31 C36 C40 . . . . 2.7(2) ?
C33 C32 C37 C38 . . . . 49.3(2) ?
C31 C32 C37 C38 . . . . -133.89(16) ?
C33 C32 C37 C39 . . . . -74.06(19) ?
C31 C32 C37 C39 . . . . 102.75(17) ?
C35 C36 C40 C41 . . . . -38.3(2) ?
C31 C36 C40 C41 . . . . 143.54(15) ?
C35 C36 C40 C42 . . . . 84.63(19) ?
C31 C36 C40 C42 . . . . -93.52(18) ?
N3 B1 C51 C56 . . . . -92.79(16) ?
C18 B1 C51 C56 . . . . 35.51(19) ?
C1 B1 C51 C56 . . . . 147.49(13) ?
N3 B1 C51 C52 . . . . 78.37(16) ?
C18 B1 C51 C52 . . . . -153.33(13) ?
C1 B1 C51 C52 . . . . -41.34(19) ?
C56 C51 C52 F52 . . . . -177.88(13) ?
B1 C51 C52 F52 . . . . 10.2(2) ?
C56 C51 C52 C53 . . . . 1.3(2) ?
B1 C51 C52 C53 . . . . -170.63(14) ?
F52 C52 C53 F53 . . . . -2.2(2) ?
C51 C52 C53 F53 . . . . 178.58(14) ?
F52 C52 C53 C54 . . . . 178.42(13) ?
C51 C52 C53 C54 . . . . -0.8(2) ?
F53 C53 C54 F54 . . . . -0.9(2) ?
C52 C53 C54 F54 . . . . 178.41(14) ?
F53 C53 C54 C55 . . . . -179.51(14) ?
C52 C53 C54 C55 . . . . -0.1(2) ?
F54 C54 C55 F55 . . . . -0.2(2) ?
C53 C54 C55 F55 . . . . 178.37(13) ?
F54 C54 C55 C56 . . . . -178.13(13) ?
C53 C54 C55 C56 . . . . 0.4(2) ?
F55 C55 C56 F56 . . . . 0.7(2) ?
C54 C55 C56 F56 . . . . 178.66(13) ?
F55 C55 C56 C51 . . . . -177.74(13) ?
C54 C55 C56 C51 . . . . 0.2(2) ?
C52 C51 C56 F56 . . . . -179.38(12) ?
B1 C51 C56 F56 . . . . -7.4(2) ?
C52 C51 C56 C55 . . . . -1.0(2) ?
B1 C51 C56 C55 . . . . 170.97(14) ?
O1 N3 C61 C66 . . . . 146.37(14) ?
B1 N3 C61 C66 . . . . -31.2(2) ?
O1 N3 C61 C62 . . . . -32.47(19) ?
B1 N3 C61 C62 . . . . 149.92(15) ?
C66 C61 C62 C63 . . . . -0.7(2) ?
N3 C61 C62 C63 . . . . 178.18(15) ?
C61 C62 C63 C64 . . . . 0.6(3) ?
C62 C63 C64 C65 . . . . 0.2(3) ?
C63 C64 C65 C66 . . . . -0.9(3) ?
C64 C65 C66 C61 . . . . 0.8(3) ?
C62 C61 C66 C65 . . . . 0.0(2) ?
N3 C61 C66 C65 . . . . -178.85(15) ?


####################################################################### 
# 
# 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_8_erk10033
_database_code_depnum_ccdc_archive 'CCDC 2157865'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2022-03-11 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2019.11-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H39 B F5 N3 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         671.54

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.5547(5)
_cell_length_b                   10.2914(4)
_cell_length_c                   20.8535(8)
_cell_angle_alpha                90
_cell_angle_beta                 110.1980(10)
_cell_angle_gamma                90
_cell_volume                     3334.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9980
_cell_measurement_theta_min      2.2359
_cell_measurement_theta_max      26.7050
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.416
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.131
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408

_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption
correction. Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M.
& Stalke D., J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   MoK\a
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            87549
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         26.81
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26

_refine_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.

The hydrogen at O1 atom was refined freely.
;

_reflns_number_total             7108
_reflns_number_gt                6054
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1025
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_number_reflns         7108
_refine_ls_number_parameters     453
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0313P)²+2.7168P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.235
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
N N 0.0061 0.0033 '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'

_computing_data_collection       'Bruker APEX3 v2019.11-0 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.73154(11) 0.57581(18) 0.72784(9) 0.0129(4) Uani d . . . 1 . .
N N1 0.63873(8) 0.49186(13) 0.60726(7) 0.0129(3) Uani d . . . 1 . .
N N2 0.75938(8) 0.56832(13) 0.60631(7) 0.0130(3) Uani d . . . 1 . .
N N3 0.82526(8) 0.62483(13) 0.76433(7) 0.0140(3) Uani d . . . 1 . .
O O1 0.88124(8) 0.51282(12) 0.76718(6) 0.0175(3) Uani d . . . 1 . .
H H1 0.9155(15) 0.539(2) 0.7475(12) 0.036(6) Uiso d . . . 1 . .
C C1 0.71560(10) 0.53908(15) 0.64874(8) 0.0130(3) Uani d . . . 1 . .
C C2 0.63457(10) 0.49264(16) 0.53950(8) 0.0154(3) Uani d . . . 1 . .
H H2 0.587444 0.465114 0.500928 0.018 Uiso calc U . R 1 . .
C C3 0.70984(10) 0.53970(16) 0.53912(8) 0.0160(3) Uani d . . . 1 . .
H H3 0.726282 0.551352 0.500125 0.019 Uiso calc U . R 1 . .
C C11 0.56640(10) 0.45659(16) 0.62773(8) 0.0139(3) Uani d . . . 1 . .
C C12 0.53335(10) 0.54903(16) 0.66198(8) 0.0154(3) Uani d . . . 1 . .
C C13 0.45642(11) 0.51732(18) 0.67217(9) 0.0194(4) Uani d . . . 1 . .
H H13 0.431858 0.577917 0.694531 0.023 Uiso calc U . R 1 . .
C C14 0.41523(11) 0.39990(18) 0.65049(9) 0.0214(4) Uani d . . . 1 . .
H H14 0.36231 0.381556 0.656929 0.026 Uiso calc U . R 1 . .
C C15 0.45135(11) 0.30940(17) 0.61943(9) 0.0191(4) Uani d . . . 1 . .
H H15 0.423306 0.228321 0.605609 0.023 Uiso calc U . R 1 . .
C C16 0.52833(10) 0.33458(16) 0.60789(8) 0.0156(3) Uani d . . . 1 . .
C C17 0.57499(11) 0.67633(16) 0.68702(8) 0.0158(3) Uani d . . . 1 . .
C C18 0.66055(10) 0.68904(16) 0.71689(8) 0.0146(3) Uani d . . . 1 . .
H H18 0.681416 0.773102 0.73322 0.017 Uiso calc U . R 1 . .
C C19 0.51472(11) 0.78934(17) 0.68185(9) 0.0207(4) Uani d . . . 1 . .
H H19A 0.484926 0.777475 0.714682 0.031 Uiso calc U . R 1 . .
H H19B 0.472355 0.793421 0.635476 0.031 Uiso calc U . R 1 . .
H H19C 0.54782 0.870369 0.692022 0.031 Uiso calc U . R 1 . .
C C20 0.56708(11) 0.22713(17) 0.57739(9) 0.0191(4) Uani d . . . 1 . .
H H20 0.624717 0.256635 0.57759 0.023 Uiso calc U . R 1 . .
C C21 0.57953(12) 0.10395(18) 0.62118(10) 0.0251(4) Uani d . . . 1 . .
H H21A 0.615575 0.124012 0.668336 0.038 Uiso calc U . R 1 . .
H H21B 0.607597 0.036951 0.602841 0.038 Uiso calc U . R 1 . .
H H21C 0.523364 0.072197 0.620353 0.038 Uiso calc U . R 1 . .
C C22 0.51042(13) 0.19704(19) 0.50339(10) 0.0261(4) Uani d . . . 1 . .
H H22A 0.453537 0.168185 0.50229 0.039 Uiso calc U . R 1 . .
H H22B 0.537312 0.128237 0.485192 0.039 Uiso calc U . R 1 . .
H H22C 0.50423 0.275495 0.475464 0.039 Uiso calc U . R 1 . .
C C31 0.84741(10) 0.61462(16) 0.62340(8) 0.0142(3) Uani d . . . 1 . .
C C32 0.91060(11) 0.52201(17) 0.62603(8) 0.0161(3) Uani d . . . 1 . .
C C33 0.99432(11) 0.56828(18) 0.63861(9) 0.0199(4) Uani d . . . 1 . .
H H33 1.039076 0.508612 0.641048 0.024 Uiso calc U . R 1 . .
C C34 1.01273(11) 0.69970(19) 0.64752(9) 0.0216(4) Uani d . . . 1 . .
H H34 1.069873 0.729278 0.656114 0.026 Uiso calc U . R 1 . .
C C35 0.94820(11) 0.78852(18) 0.64397(9) 0.0195(4) Uani d . . . 1 . .
H H35 0.961751 0.878423 0.649877 0.023 Uiso calc U . R 1 . .
C C36 0.86360(11) 0.74794(17) 0.63184(8) 0.0165(3) Uani d . . . 1 . .
C C37 0.89145(11) 0.37731(17) 0.61456(9) 0.0194(4) Uani d . . . 1 . .
H H37 0.830442 0.362493 0.611248 0.023 Uiso calc U . R 1 . .
C C38 0.90052(13) 0.3347(2) 0.54692(10) 0.0292(4) Uani d . . . 1 . .
H H38A 0.863291 0.388628 0.509657 0.044 Uiso calc U . R 1 . .
H H38B 0.883553 0.243412 0.538134 0.044 Uiso calc U . R 1 . .
H H38C 0.960498 0.344983 0.549727 0.044 Uiso calc U . R 1 . .
C C39 0.94955(12) 0.29657(19) 0.67418(10) 0.0259(4) Uani d . . . 1 . .
H H39A 1.009947 0.313737 0.68015 0.039 Uiso calc U . R 1 . .
H H39B 0.937163 0.204059 0.66456 0.039 Uiso calc U . R 1 . .
H H39C 0.938799 0.320152 0.716051 0.039 Uiso calc U . R 1 . .
C C40 0.79239(11) 0.84586(17) 0.62515(9) 0.0184(4) Uani d . . . 1 . .
H H40 0.746825 0.801106 0.638343 0.022 Uiso calc U . R 1 . .
C C41 0.75147(14) 0.8904(2) 0.55088(10) 0.0337(5) Uani d . . . 1 . .
H H41A 0.794778 0.934918 0.536574 0.051 Uiso calc U . R 1 . .
H H41B 0.703916 0.950169 0.547024 0.051 Uiso calc U . R 1 . .
H H41C 0.729519 0.814742 0.521505 0.051 Uiso calc U . R 1 . .
C C42 0.82369(13) 0.96211(19) 0.67244(11) 0.0317(5) Uani d . . . 1 . .
H H42A 0.856073 0.931513 0.718711 0.048 Uiso calc U . R 1 . .
H H42B 0.774119 1.01332 0.673201 0.048 Uiso calc U . R 1 . .
H H42C 0.861014 1.016295 0.655838 0.048 Uiso calc U . R 1 . .
C C51 0.71630(10) 0.45070(16) 0.77219(8) 0.0132(3) Uani d . . . 1 . .
C C52 0.73651(10) 0.32316(16) 0.76231(8) 0.0156(3) Uani d . . . 1 . .
C C53 0.73788(11) 0.22258(16) 0.80659(9) 0.0184(4) Uani d . . . 1 . .
C C54 0.71928(11) 0.24742(17) 0.86491(9) 0.0190(4) Uani d . . . 1 . .
C C55 0.69822(10) 0.37233(18) 0.87727(8) 0.0178(3) Uani d . . . 1 . .
C C56 0.69627(10) 0.46939(16) 0.83099(8) 0.0154(3) Uani d . . . 1 . .
C C61 0.84566(10) 0.67296(16) 0.83210(8) 0.0144(3) Uani d . . . 1 . .
C C62 0.88810(10) 0.59844(17) 0.89028(9) 0.0171(3) Uani d . . . 1 . .
H H62 0.904973 0.511777 0.885514 0.02 Uiso calc U . R 1 . .
C C63 0.90548(11) 0.65150(19) 0.95496(9) 0.0214(4) Uani d . . . 1 . .
H H63 0.934389 0.600454 0.994136 0.026 Uiso calc U . R 1 . .
C C64 0.88134(11) 0.77768(19) 0.96329(9) 0.0223(4) Uani d . . . 1 . .
H H64 0.892881 0.812753 1.00771 0.027 Uiso calc U . R 1 . .
C C65 0.84006(11) 0.85182(17) 0.90570(9) 0.0202(4) Uani d . . . 1 . .
H H65 0.823085 0.938291 0.910767 0.024 Uiso calc U . R 1 . .
C C66 0.82335(10) 0.80099(17) 0.84092(9) 0.0173(3) Uani d . . . 1 . .
H H66 0.79641 0.85377 0.802005 0.021 Uiso calc U . R 1 . .
F F52 0.75648(6) 0.29067(10) 0.70644(5) 0.0199(2) Uani d . . . 1 . .
F F53 0.75760(7) 0.10013(10) 0.79385(6) 0.0278(3) Uani d . . . 1 . .
F F54 0.72011(7) 0.15088(11) 0.90853(5) 0.0272(3) Uani d . . . 1 . .
F F55 0.67877(7) 0.39703(11) 0.93360(5) 0.0257(2) Uani d . . . 1 . .
F F56 0.67508(6) 0.58884(10) 0.84728(5) 0.0204(2) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 N3 . 1.557(2) ?
B1 C18 . 1.614(2) ?
B1 C1 . 1.623(2) ?
B1 C51 . 1.655(2) ?
N1 C1 . 1.358(2) ?
N1 C2 . 1.391(2) ?
N1 C11 . 1.449(2) ?
N2 C1 . 1.357(2) ?
N2 C3 . 1.389(2) ?
N2 C31 . 1.456(2) ?
N3 C61 . 1.424(2) ?
N3 O1 . 1.4673(17) ?
O1 H1 . 0.85(2) ?
C2 C3 . 1.339(2) ?
C2 H2 . 0.95 ?
C3 H3 . 0.95 ?
C11 C16 . 1.402(2) ?
C11 C12 . 1.409(2) ?
C12 C13 . 1.400(2) ?
C12 C17 . 1.489(2) ?
C13 C14 . 1.384(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.383(3) ?
C14 H14 . 0.95 ?
C15 C16 . 1.400(2) ?
C15 H15 . 0.95 ?
C16 C20 . 1.523(2) ?
C17 C18 . 1.342(2) ?
C17 C19 . 1.512(2) ?
C18 H18 . 0.95 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C20 C21 . 1.534(2) ?
C20 C22 . 1.535(2) ?
C20 H20 . 1.0 ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
C31 C36 . 1.397(2) ?
C31 C32 . 1.402(2) ?
C32 C33 . 1.402(2) ?
C32 C37 . 1.524(2) ?
C33 C34 . 1.385(3) ?
C33 H33 . 0.95 ?
C34 C35 . 1.388(3) ?
C34 H34 . 0.95 ?
C35 C36 . 1.398(2) ?
C35 H35 . 0.95 ?
C36 C40 . 1.520(2) ?
C37 C39 . 1.528(2) ?
C37 C38 . 1.533(3) ?
C37 H37 . 1.0 ?
C38 H38A . 0.98 ?
C38 H38B . 0.98 ?
C38 H38C . 0.98 ?
C39 H39A . 0.98 ?
C39 H39B . 0.98 ?
C39 H39C . 0.98 ?
C40 C42 . 1.523(3) ?
C40 C41 . 1.531(3) ?
C40 H40 . 1.0 ?
C41 H41A . 0.98 ?
C41 H41B . 0.98 ?
C41 H41C . 0.98 ?
C42 H42A . 0.98 ?
C42 H42B . 0.98 ?
C42 H42C . 0.98 ?
C51 C52 . 1.387(2) ?
C51 C56 . 1.390(2) ?
C52 F52 . 1.3581(19) ?
C52 C53 . 1.382(2) ?
C53 F53 . 1.351(2) ?
C53 C54 . 1.378(3) ?
C54 F54 . 1.3439(19) ?
C54 C55 . 1.379(3) ?
C55 F55 . 1.3451(19) ?
C55 C56 . 1.382(2) ?
C56 F56 . 1.3534(19) ?
C61 C66 . 1.398(2) ?
C61 C62 . 1.402(2) ?
C62 C63 . 1.390(2) ?
C62 H62 . 0.95 ?
C63 C64 . 1.387(3) ?
C63 H63 . 0.95 ?
C64 C65 . 1.387(3) ?
C64 H64 . 0.95 ?
C65 C66 . 1.385(2) ?
C65 H65 . 0.95 ?
C66 H66 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 B1 C18 . . 112.90(14) ?
N3 B1 C1 . . 110.92(13) ?
C18 B1 C1 . . 99.75(13) ?
N3 B1 C51 . . 107.31(13) ?
C18 B1 C51 . . 113.37(13) ?
C1 B1 C51 . . 112.60(13) ?
C1 N1 C2 . . 110.60(13) ?
C1 N1 C11 . . 126.15(14) ?
C2 N1 C11 . . 122.99(13) ?
C1 N2 C3 . . 110.39(13) ?
C1 N2 C31 . . 128.89(14) ?
C3 N2 C31 . . 120.60(13) ?
C61 N3 O1 . . 107.64(12) ?
C61 N3 B1 . . 116.90(12) ?
O1 N3 B1 . . 105.90(12) ?
N3 O1 H1 . . 104.1(16) ?
N2 C1 N1 . . 104.96(14) ?
N2 C1 B1 . . 132.46(14) ?
N1 C1 B1 . . 121.24(14) ?
C3 C2 N1 . . 106.75(14) ?
C3 C2 H2 . . 126.6 ?
N1 C2 H2 . . 126.6 ?
C2 C3 N2 . . 107.29(14) ?
C2 C3 H3 . . 126.4 ?
N2 C3 H3 . . 126.4 ?
C16 C11 C12 . . 122.73(15) ?
C16 C11 N1 . . 118.07(14) ?
C12 C11 N1 . . 119.03(14) ?
C13 C12 C11 . . 116.90(16) ?
C13 C12 C17 . . 119.16(15) ?
C11 C12 C17 . . 123.94(14) ?
C14 C13 C12 . . 121.67(16) ?
C14 C13 H13 . . 119.2 ?
C12 C13 H13 . . 119.2 ?
C15 C14 C13 . . 119.81(16) ?
C15 C14 H14 . . 120.1 ?
C13 C14 H14 . . 120.1 ?
C14 C15 C16 . . 121.48(16) ?
C14 C15 H15 . . 119.3 ?
C16 C15 H15 . . 119.3 ?
C15 C16 C11 . . 117.28(16) ?
C15 C16 C20 . . 118.48(15) ?
C11 C16 C20 . . 124.21(15) ?
C18 C17 C12 . . 122.35(15) ?
C18 C17 C19 . . 121.52(16) ?
C12 C17 C19 . . 115.96(14) ?
C17 C18 B1 . . 126.54(15) ?
C17 C18 H18 . . 116.7 ?
B1 C18 H18 . . 116.7 ?
C17 C19 H19A . . 109.5 ?
C17 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C17 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C16 C20 C21 . . 109.91(14) ?
C16 C20 C22 . . 111.52(14) ?
C21 C20 C22 . . 109.97(15) ?
C16 C20 H20 . . 108.5 ?
C21 C20 H20 . . 108.5 ?
C22 C20 H20 . . 108.5 ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C20 C22 H22A . . 109.5 ?
C20 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C20 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C36 C31 C32 . . 123.68(15) ?
C36 C31 N2 . . 118.98(14) ?
C32 C31 N2 . . 117.21(14) ?
C33 C32 C31 . . 116.90(16) ?
C33 C32 C37 . . 119.99(15) ?
C31 C32 C37 . . 123.10(15) ?
C34 C33 C32 . . 120.96(16) ?
C34 C33 H33 . . 119.5 ?
C32 C33 H33 . . 119.5 ?
C33 C34 C35 . . 120.41(16) ?
C33 C34 H34 . . 119.8 ?
C35 C34 H34 . . 119.8 ?
C34 C35 C36 . . 121.15(17) ?
C34 C35 H35 . . 119.4 ?
C36 C35 H35 . . 119.4 ?
C31 C36 C35 . . 116.90(16) ?
C31 C36 C40 . . 122.04(15) ?
C35 C36 C40 . . 121.01(15) ?
C32 C37 C39 . . 111.42(15) ?
C32 C37 C38 . . 110.03(15) ?
C39 C37 C38 . . 111.04(15) ?
C32 C37 H37 . . 108.1 ?
C39 C37 H37 . . 108.1 ?
C38 C37 H37 . . 108.1 ?
C37 C38 H38A . . 109.5 ?
C37 C38 H38B . . 109.5 ?
H38A C38 H38B . . 109.5 ?
C37 C38 H38C . . 109.5 ?
H38A C38 H38C . . 109.5 ?
H38B C38 H38C . . 109.5 ?
C37 C39 H39A . . 109.5 ?
C37 C39 H39B . . 109.5 ?
H39A C39 H39B . . 109.5 ?
C37 C39 H39C . . 109.5 ?
H39A C39 H39C . . 109.5 ?
H39B C39 H39C . . 109.5 ?
C36 C40 C42 . . 112.43(15) ?
C36 C40 C41 . . 110.47(14) ?
C42 C40 C41 . . 110.64(16) ?
C36 C40 H40 . . 107.7 ?
C42 C40 H40 . . 107.7 ?
C41 C40 H40 . . 107.7 ?
C40 C41 H41A . . 109.5 ?
C40 C41 H41B . . 109.5 ?
H41A C41 H41B . . 109.5 ?
C40 C41 H41C . . 109.5 ?
H41A C41 H41C . . 109.5 ?
H41B C41 H41C . . 109.5 ?
C40 C42 H42A . . 109.5 ?
C40 C42 H42B . . 109.5 ?
H42A C42 H42B . . 109.5 ?
C40 C42 H42C . . 109.5 ?
H42A C42 H42C . . 109.5 ?
H42B C42 H42C . . 109.5 ?
C52 C51 C56 . . 113.90(15) ?
C52 C51 B1 . . 124.20(14) ?
C56 C51 B1 . . 120.95(14) ?
F52 C52 C53 . . 115.85(15) ?
F52 C52 C51 . . 120.19(15) ?
C53 C52 C51 . . 123.96(15) ?
F53 C53 C54 . . 119.32(15) ?
F53 C53 C52 . . 121.10(16) ?
C54 C53 C52 . . 119.58(16) ?
F54 C54 C53 . . 120.47(16) ?
F54 C54 C55 . . 120.44(16) ?
C53 C54 C55 . . 119.07(16) ?
F55 C55 C54 . . 119.44(15) ?
F55 C55 C56 . . 121.23(16) ?
C54 C55 C56 . . 119.32(15) ?
F56 C56 C55 . . 115.28(14) ?
F56 C56 C51 . . 120.57(15) ?
C55 C56 C51 . . 124.14(16) ?
C66 C61 C62 . . 118.57(15) ?
C66 C61 N3 . . 118.40(15) ?
C62 C61 N3 . . 123.03(15) ?
C63 C62 C61 . . 119.92(16) ?
C63 C62 H62 . . 120.0 ?
C61 C62 H62 . . 120.0 ?
C64 C63 C62 . . 121.15(17) ?
C64 C63 H63 . . 119.4 ?
C62 C63 H63 . . 119.4 ?
C63 C64 C65 . . 118.91(16) ?
C63 C64 H64 . . 120.5 ?
C65 C64 H64 . . 120.5 ?
C66 C65 C64 . . 120.64(17) ?
C66 C65 H65 . . 119.7 ?
C64 C65 H65 . . 119.7 ?
C65 C66 C61 . . 120.77(16) ?
C65 C66 H66 . . 119.6 ?
C61 C66 H66 . . 119.6 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C18 B1 N3 C61 . . . . 62.83(18) ?
C1 B1 N3 C61 . . . . 173.83(13) ?
C51 B1 N3 C61 . . . . -62.81(17) ?
C18 B1 N3 O1 . . . . -177.31(12) ?
C1 B1 N3 O1 . . . . -66.32(15) ?
C51 B1 N3 O1 . . . . 57.05(15) ?
C3 N2 C1 N1 . . . . 0.16(17) ?
C31 N2 C1 N1 . . . . -175.74(15) ?
C3 N2 C1 B1 . . . . -166.31(16) ?
C31 N2 C1 B1 . . . . 17.8(3) ?
C2 N1 C1 N2 . . . . -0.42(17) ?
C11 N1 C1 N2 . . . . -174.74(14) ?
C2 N1 C1 B1 . . . . 167.93(14) ?
C11 N1 C1 B1 . . . . -6.4(2) ?
N3 B1 C1 N2 . . . . -16.5(2) ?
C18 B1 C1 N2 . . . . 102.71(19) ?
C51 B1 C1 N2 . . . . -136.79(17) ?
N3 B1 C1 N1 . . . . 178.80(14) ?
C18 B1 C1 N1 . . . . -61.96(18) ?
C51 B1 C1 N1 . . . . 58.53(19) ?
C1 N1 C2 C3 . . . . 0.53(19) ?
C11 N1 C2 C3 . . . . 175.07(15) ?
N1 C2 C3 N2 . . . . -0.41(18) ?
C1 N2 C3 C2 . . . . 0.17(19) ?
C31 N2 C3 C2 . . . . 176.46(14) ?
C1 N1 C11 C16 . . . . -130.00(17) ?
C2 N1 C11 C16 . . . . 56.3(2) ?
C1 N1 C11 C12 . . . . 54.7(2) ?
C2 N1 C11 C12 . . . . -118.99(17) ?
C16 C11 C12 C13 . . . . -3.8(2) ?
N1 C11 C12 C13 . . . . 171.28(14) ?
C16 C11 C12 C17 . . . . 176.53(15) ?
N1 C11 C12 C17 . . . . -8.4(2) ?
C11 C12 C13 C14 . . . . 0.9(2) ?
C17 C12 C13 C14 . . . . -179.45(16) ?
C12 C13 C14 C15 . . . . 1.6(3) ?
C13 C14 C15 C16 . . . . -1.4(3) ?
C14 C15 C16 C11 . . . . -1.4(2) ?
C14 C15 C16 C20 . . . . 176.32(16) ?
C12 C11 C16 C15 . . . . 4.1(2) ?
N1 C11 C16 C15 . . . . -171.06(14) ?
C12 C11 C16 C20 . . . . -173.50(15) ?
N1 C11 C16 C20 . . . . 11.4(2) ?
C13 C12 C17 C18 . . . . 139.49(17) ?
C11 C12 C17 C18 . . . . -40.9(2) ?
C13 C12 C17 C19 . . . . -35.9(2) ?
C11 C12 C17 C19 . . . . 143.71(16) ?
C12 C17 C18 B1 . . . . 2.8(3) ?
C19 C17 C18 B1 . . . . 177.98(15) ?
N3 B1 C18 C17 . . . . 179.88(15) ?
C1 B1 C18 C17 . . . . 62.1(2) ?
C51 B1 C18 C17 . . . . -57.8(2) ?
C15 C16 C20 C21 . . . . -55.0(2) ?
C11 C16 C20 C21 . . . . 122.58(17) ?
C15 C16 C20 C22 . . . . 67.3(2) ?
C11 C16 C20 C22 . . . . -115.18(18) ?
C1 N2 C31 C36 . . . . -86.1(2) ?
C3 N2 C31 C36 . . . . 98.36(18) ?
C1 N2 C31 C32 . . . . 98.0(2) ?
C3 N2 C31 C32 . . . . -77.58(19) ?
C36 C31 C32 C33 . . . . 0.7(2) ?
N2 C31 C32 C33 . . . . 176.40(14) ?
C36 C31 C32 C37 . . . . -178.06(16) ?
N2 C31 C32 C37 . . . . -2.3(2) ?
C31 C32 C33 C34 . . . . -0.4(3) ?
C37 C32 C33 C34 . . . . 178.42(16) ?
C32 C33 C34 C35 . . . . -0.2(3) ?
C33 C34 C35 C36 . . . . 0.4(3) ?
C32 C31 C36 C35 . . . . -0.4(2) ?
N2 C31 C36 C35 . . . . -176.08(14) ?
C32 C31 C36 C40 . . . . 176.92(15) ?
N2 C31 C36 C40 . . . . 1.3(2) ?
C34 C35 C36 C31 . . . . -0.1(2) ?
C34 C35 C36 C40 . . . . -177.52(16) ?
C33 C32 C37 C39 . . . . 55.7(2) ?
C31 C32 C37 C39 . . . . -125.55(17) ?
C33 C32 C37 C38 . . . . -67.9(2) ?
C31 C32 C37 C38 . . . . 110.83(18) ?
C31 C36 C40 C42 . . . . 147.12(17) ?
C35 C36 C40 C42 . . . . -35.6(2) ?
C31 C36 C40 C41 . . . . -88.7(2) ?
C35 C36 C40 C41 . . . . 88.5(2) ?
N3 B1 C51 C52 . . . . -87.18(18) ?
C18 B1 C51 C52 . . . . 147.47(15) ?
C1 B1 C51 C52 . . . . 35.2(2) ?
N3 B1 C51 C56 . . . . 81.00(17) ?
C18 B1 C51 C56 . . . . -44.4(2) ?
C1 B1 C51 C56 . . . . -156.67(14) ?
C56 C51 C52 F52 . . . . 179.29(14) ?
B1 C51 C52 F52 . . . . -11.8(2) ?
C56 C51 C52 C53 . . . . -0.6(2) ?
B1 C51 C52 C53 . . . . 168.29(15) ?
F52 C52 C53 F53 . . . . -0.3(2) ?
C51 C52 C53 F53 . . . . 179.59(15) ?
F52 C52 C53 C54 . . . . 179.32(14) ?
C51 C52 C53 C54 . . . . -0.8(3) ?
F53 C53 C54 F54 . . . . -0.5(2) ?
C52 C53 C54 F54 . . . . 179.86(15) ?
F53 C53 C54 C55 . . . . -179.26(15) ?
C52 C53 C54 C55 . . . . 1.1(2) ?
F54 C54 C55 F55 . . . . 0.3(2) ?
C53 C54 C55 F55 . . . . 179.05(15) ?
F54 C54 C55 C56 . . . . -178.79(14) ?
C53 C54 C55 C56 . . . . 0.0(2) ?
F55 C55 C56 F56 . . . . 1.0(2) ?
C54 C55 C56 F56 . . . . -179.93(14) ?
F55 C55 C56 C51 . . . . 179.44(15) ?
C54 C55 C56 C51 . . . . -1.5(3) ?
C52 C51 C56 F56 . . . . -179.89(14) ?
B1 C51 C56 F56 . . . . 10.8(2) ?
C52 C51 C56 C55 . . . . 1.8(2) ?
B1 C51 C56 C55 . . . . -167.54(15) ?
O1 N3 C61 C66 . . . . 159.09(13) ?
B1 N3 C61 C66 . . . . -81.98(18) ?
O1 N3 C61 C62 . . . . -20.00(19) ?
B1 N3 C61 C62 . . . . 98.93(18) ?
C66 C61 C62 C63 . . . . 1.3(2) ?
N3 C61 C62 C63 . . . . -179.59(15) ?
C61 C62 C63 C64 . . . . 0.2(3) ?
C62 C63 C64 C65 . . . . -0.8(3) ?
C63 C64 C65 C66 . . . . -0.2(3) ?
C64 C65 C66 C61 . . . . 1.7(3) ?
C62 C61 C66 C65 . . . . -2.2(2) ?
N3 C61 C66 C65 . . . . 178.63(15) ?


