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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_9553
_database_code_depnum_ccdc_archive 'CCDC 2068943'
_audit_update_record             
;
2021-08-06 deposited with the CCDC.	2021-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H26 B F2 N O'
_chemical_formula_weight         417.29

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'
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'
F F 0.0727 0.0534 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   7.5642(5)
_cell_length_b                   9.5549(6)
_cell_length_c                   28.5373(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2062.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4239
_cell_measurement_theta_min      5.4390
_cell_measurement_theta_max      70.6920

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.750
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86055
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 8.1281
_diffrn_reflns_number            13748
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         4.881
_diffrn_reflns_theta_max         67.236
_diffrn_reflns_theta_full        67.236
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3694
_reflns_number_gt                2895
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0544P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0032(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 961 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.14(15)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3694
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.1040(3) 0.4673(2) 0.33608(8) 0.0423(6) Uani 1 1 d . . . . .
F2 F 0.2428(3) 0.4183(2) 0.26777(8) 0.0479(7) Uani 1 1 d . . . . .
O1 O 0.3934(4) 0.3817(3) 0.33663(9) 0.0383(7) Uani 1 1 d . . . . .
N1 N 0.3315(4) 0.6227(3) 0.30969(10) 0.0338(7) Uani 1 1 d . . . . .
C4 C 0.5247(5) 0.4320(4) 0.36331(13) 0.0329(9) Uani 1 1 d . . . . .
C21 C 0.1659(5) 0.8472(4) 0.29838(14) 0.0402(10) Uani 1 1 d . . . . .
C17 C 0.4676(5) 0.6692(4) 0.33278(12) 0.0330(9) Uani 1 1 d . . . . .
C2 C 0.6826(5) 0.6251(4) 0.40028(13) 0.0342(9) Uani 1 1 d . . . . .
C10 C 0.3726(5) 0.3333(4) 0.46273(14) 0.0400(10) Uani 1 1 d . . . . .
C13 C 0.4086(6) 0.6248(4) 0.46736(13) 0.0394(10) Uani 1 1 d . . . . .
C5 C 0.6179(6) 0.3340(4) 0.39110(13) 0.0375(9) Uani 1 1 d . . . . .
C11 C 0.4864(6) 0.3950(5) 0.49504(13) 0.0432(10) Uani 1 1 d . . . . .
H11 H 0.551783 0.338465 0.515145 0.052 Uiso 1 1 calc R U . . .
C22 C 0.0807(6) 0.8445(4) 0.34148(14) 0.0432(10) Uani 1 1 d . . . . .
H22 H 0.057823 0.759032 0.355872 0.052 Uiso 1 1 calc R U . . .
C7 C 0.7900(5) 0.5267(5) 0.42050(13) 0.0401(10) Uani 1 1 d . . . . .
H7 H 0.885501 0.556778 0.438379 0.048 Uiso 1 1 calc R U . . .
C3 C 0.5618(5) 0.5766(4) 0.36505(12) 0.0328(9) Uani 1 1 d . . . . .
C14 C 0.2723(5) 0.5639(4) 0.44233(14) 0.0394(10) Uani 1 1 d . . . . .
H14 H 0.191785 0.620914 0.426733 0.047 Uiso 1 1 calc R U . . .
C15 C 0.2530(5) 0.4202(4) 0.43999(13) 0.0393(9) Uani 1 1 d . . . . .
H15 H 0.159688 0.381554 0.423154 0.047 Uiso 1 1 calc R U . . .
C26 C 0.1945(6) 0.9762(5) 0.27722(16) 0.0520(12) Uani 1 1 d . . . . .
H26 H 0.249598 0.980281 0.248111 0.062 Uiso 1 1 calc R U . . .
C19 C 0.2222(6) 0.7100(4) 0.27649(13) 0.0384(10) Uani 1 1 d . . . . .
H19 H 0.112647 0.657188 0.271739 0.046 Uiso 1 1 calc R U . . .
C12 C 0.5040(6) 0.5391(5) 0.49775(13) 0.0431(10) Uani 1 1 d . . . . .
H12 H 0.579389 0.578691 0.519828 0.052 Uiso 1 1 calc R U . . .
B1 B 0.2653(7) 0.4684(5) 0.31299(15) 0.0363(10) Uani 1 1 d . . . . .
C6 C 0.7620(6) 0.3838(4) 0.41537(13) 0.0413(10) Uani 1 1 d . . . . .
H6 H 0.841705 0.320980 0.428519 0.050 Uiso 1 1 calc R U . . .
C1 C 0.6585(6) 0.7620(4) 0.42630(15) 0.0427(10) Uani 1 1 d . . . . .
H1A H 0.663105 0.838660 0.404048 0.051 Uiso 1 1 calc R U . . .
H1B H 0.755294 0.773938 0.448222 0.051 Uiso 1 1 calc R U . . .
C18 C 0.5415(5) 0.8142(4) 0.32456(14) 0.0406(10) Uani 1 1 d . . . . .
H18A H 0.521816 0.840815 0.292547 0.061 Uiso 1 1 calc R U . . .
H18B H 0.666044 0.814173 0.330975 0.061 Uiso 1 1 calc R U . . .
H18C H 0.483426 0.879567 0.344948 0.061 Uiso 1 1 calc R U . . .
C23 C 0.0289(6) 0.9681(5) 0.36345(18) 0.0554(12) Uani 1 1 d . . . . .
H23 H -0.027428 0.965355 0.392397 0.066 Uiso 1 1 calc R U . . .
C16 C 0.4773(7) 0.7689(4) 0.45399(15) 0.0490(12) Uani 1 1 d . . . . .
H16A H 0.493607 0.824026 0.482205 0.059 Uiso 1 1 calc R U . . .
H16B H 0.389805 0.815770 0.434731 0.059 Uiso 1 1 calc R U . . .
C8 C 0.5419(6) 0.1915(4) 0.40024(16) 0.0463(11) Uani 1 1 d . . . . .
H8A H 0.637755 0.126197 0.405952 0.056 Uiso 1 1 calc R U . . .
H8B H 0.478915 0.160170 0.372554 0.056 Uiso 1 1 calc R U . . .
C20 C 0.3090(7) 0.7185(5) 0.22818(14) 0.0538(12) Uani 1 1 d . . . . .
H20A H 0.420565 0.765722 0.230746 0.081 Uiso 1 1 calc R U . . .
H20B H 0.233370 0.769361 0.207203 0.081 Uiso 1 1 calc R U . . .
H20C H 0.327439 0.625686 0.216253 0.081 Uiso 1 1 calc R U . . .
C9 C 0.4102(7) 0.1893(5) 0.44400(15) 0.0532(12) Uani 1 1 d . . . . .
H9A H 0.299838 0.145806 0.434634 0.064 Uiso 1 1 calc R U . . .
H9B H 0.461482 0.132691 0.468742 0.064 Uiso 1 1 calc R U . . .
C25 C 0.1417(7) 1.0989(5) 0.2991(2) 0.0645(15) Uani 1 1 d . . . . .
H25 H 0.160942 1.184516 0.284488 0.077 Uiso 1 1 calc R U . . .
C24 C 0.0621(7) 1.0950(5) 0.3418(2) 0.0646(15) Uani 1 1 d . . . . .
H24 H 0.029830 1.177968 0.356554 0.078 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.386(5) . ?
F2 B1 1.387(5) . ?
O1 C4 1.341(5) . ?
O1 B1 1.442(5) . ?
N1 C17 1.300(5) . ?
N1 C19 1.509(5) . ?
N1 B1 1.560(5) . ?
C4 C3 1.411(5) . ?
C4 C5 1.415(5) . ?
C21 C22 1.389(6) . ?
C21 C26 1.389(5) . ?
C21 C19 1.513(6) . ?
C17 C3 1.462(5) . ?
C17 C18 1.512(5) . ?
C2 C7 1.370(5) . ?
C2 C3 1.435(5) . ?
C2 C1 1.515(5) . ?
C10 C15 1.389(5) . ?
C10 C11 1.392(6) . ?
C10 C9 1.504(6) . ?
C13 C14 1.383(6) . ?
C13 C12 1.394(6) . ?
C13 C16 1.520(6) . ?
C5 C6 1.376(6) . ?
C5 C8 1.501(6) . ?
C11 C12 1.386(6) . ?
C11 H11 0.9300 . ?
C22 C23 1.393(6) . ?
C22 H22 0.9300 . ?
C7 C6 1.389(6) . ?
C7 H7 0.9300 . ?
C14 C15 1.383(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C26 C25 1.388(7) . ?
C26 H26 0.9300 . ?
C19 C20 1.529(6) . ?
C19 H19 0.9800 . ?
C12 H12 0.9300 . ?
C6 H6 0.9300 . ?
C1 C16 1.583(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C23 C24 1.383(7) . ?
C23 H23 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C8 C9 1.598(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C25 C24 1.360(7) . ?
C25 H25 0.9300 . ?
C24 H24 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 B1 123.9(3) . . ?
C17 N1 C19 124.3(3) . . ?
C17 N1 B1 123.1(3) . . ?
C19 N1 B1 112.6(3) . . ?
O1 C4 C3 121.2(3) . . ?
O1 C4 C5 116.8(3) . . ?
C3 C4 C5 122.0(4) . . ?
C22 C21 C26 118.3(4) . . ?
C22 C21 C19 118.7(3) . . ?
C26 C21 C19 123.0(4) . . ?
N1 C17 C3 119.9(3) . . ?
N1 C17 C18 121.8(4) . . ?
C3 C17 C18 118.1(3) . . ?
C7 C2 C3 116.8(4) . . ?
C7 C2 C1 117.2(3) . . ?
C3 C2 C1 123.0(3) . . ?
C15 C10 C11 117.4(4) . . ?
C15 C10 C9 120.3(4) . . ?
C11 C10 C9 120.4(4) . . ?
C14 C13 C12 117.4(4) . . ?
C14 C13 C16 120.4(4) . . ?
C12 C13 C16 120.7(4) . . ?
C6 C5 C4 116.6(4) . . ?
C6 C5 C8 122.0(4) . . ?
C4 C5 C8 120.5(4) . . ?
C12 C11 C10 121.1(4) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C21 C22 C23 120.9(4) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C2 C7 C6 122.7(4) . . ?
C2 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C4 C3 C2 117.9(3) . . ?
C4 C3 C17 118.2(3) . . ?
C2 C3 C17 123.8(3) . . ?
C13 C14 C15 121.4(4) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C10 120.1(4) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
C25 C26 C21 120.6(5) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
N1 C19 C21 112.0(3) . . ?
N1 C19 C20 111.1(4) . . ?
C21 C19 C20 116.6(3) . . ?
N1 C19 H19 105.4 . . ?
C21 C19 H19 105.4 . . ?
C20 C19 H19 105.4 . . ?
C11 C12 C13 120.0(4) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
F1 B1 F2 109.4(4) . . ?
F1 B1 O1 111.4(3) . . ?
F2 B1 O1 108.7(3) . . ?
F1 B1 N1 108.5(3) . . ?
F2 B1 N1 108.0(3) . . ?
O1 B1 N1 110.8(3) . . ?
C5 C6 C7 120.9(4) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C2 C1 C16 112.6(3) . . ?
C2 C1 H1A 109.1 . . ?
C16 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
C16 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C23 C22 119.4(5) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C13 C16 C1 112.5(3) . . ?
C13 C16 H16A 109.1 . . ?
C1 C16 H16A 109.1 . . ?
C13 C16 H16B 109.1 . . ?
C1 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C5 C8 C9 112.8(3) . . ?
C5 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C5 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 C9 C8 112.6(3) . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C24 C25 C26 120.5(5) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C25 C24 C23 120.3(5) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.047



####################################################################### 
# 
# 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_exp_10072
_database_code_depnum_ccdc_archive 'CCDC 2068947'
_audit_update_record             
;
2021-08-06 deposited with the CCDC.	2021-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H24 B F2 N O'
_chemical_formula_weight         403.26

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'
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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   9.9238(6)
_cell_length_b                   12.6103(8)
_cell_length_c                   16.1717(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2023.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3220
_cell_measurement_theta_min      5.1880
_cell_measurement_theta_max      62.6900

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.747
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_T_min  0.59013
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14140
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.446
_diffrn_reflns_theta_max         67.246
_diffrn_reflns_theta_full        67.246
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3638
_reflns_number_gt                2700
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0522P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0047(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 872 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3638
_refine_ls_number_parameters     273
_refine_ls_number_restraints     1044
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1238
_refine_ls_wR_factor_gt          0.1080
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.9722(3) 0.7925(2) 0.51451(16) 0.0876(9) Uani 1 1 d . U . . .
F2 F 0.8435(3) 0.6454(2) 0.50498(15) 0.0843(8) Uani 1 1 d . U . . .
N1 N 1.0424(3) 0.6367(2) 0.5879(2) 0.0556(8) Uani 1 1 d . U . . .
O1 O 0.8458(3) 0.74527(19) 0.62648(15) 0.0551(7) Uani 1 1 d . U . . .
B1 B 0.9217(5) 0.7060(4) 0.5579(3) 0.0586(11) Uani 1 1 d . U . . .
C11 C 0.5484(4) 0.5495(3) 0.7826(3) 0.0619(10) Uani 1 1 d . U . . .
H11 H 0.485750 0.568732 0.822605 0.074 Uiso 1 1 calc R U . . .
C12 C 0.6366(5) 0.4664(3) 0.7977(3) 0.0690(12) Uani 1 1 d . U . . .
H12 H 0.633703 0.430883 0.848079 0.083 Uiso 1 1 calc R U . . .
C13 C 0.7288(5) 0.4363(3) 0.7381(3) 0.0665(11) Uani 1 1 d . U . . .
C14 C 0.7123(4) 0.4763(3) 0.6593(3) 0.0632(11) Uani 1 1 d . U . . .
H14 H 0.761115 0.447067 0.615815 0.076 Uiso 1 1 calc R U . . .
C15 C 0.6247(4) 0.5589(3) 0.6439(3) 0.0588(10) Uani 1 1 d . U . . .
H15 H 0.613872 0.584235 0.590319 0.071 Uiso 1 1 calc R U . . .
C10 C 0.5530(4) 0.6041(3) 0.7083(2) 0.0552(9) Uani 1 1 d . U . . .
C9 C 0.5117(4) 0.7192(3) 0.7049(3) 0.0690(12) Uani 1 1 d . U . . .
H9A H 0.434815 0.729955 0.741012 0.083 Uiso 1 1 calc R U . . .
H9B H 0.483810 0.736416 0.648991 0.083 Uiso 1 1 calc R U . . .
C8 C 0.6283(4) 0.7965(3) 0.7316(3) 0.0625(11) Uani 1 1 d . U . . .
H8A H 0.650796 0.842145 0.685317 0.075 Uiso 1 1 calc R U . . .
H8B H 0.596484 0.841237 0.776311 0.075 Uiso 1 1 calc R U . . .
C5 C 0.7535(4) 0.7393(3) 0.7594(2) 0.0497(9) Uani 1 1 d . U . . .
C6 C 0.7701(4) 0.7041(3) 0.8390(2) 0.0602(10) Uani 1 1 d . U . . .
H6 H 0.724104 0.738371 0.881409 0.072 Uiso 1 1 calc R U . . .
C7 C 0.8529(4) 0.6195(4) 0.8583(3) 0.0646(10) Uani 1 1 d . U . . .
H7 H 0.856214 0.595513 0.912649 0.078 Uiso 1 1 calc R U . . .
C2 C 0.9307(4) 0.5699(3) 0.7995(2) 0.0558(10) Uani 1 1 d . U . . .
C3 C 0.9450(4) 0.6234(3) 0.7221(2) 0.0476(8) Uani 1 1 d . U . . .
C4 C 0.8502(4) 0.7028(3) 0.7019(2) 0.0460(8) Uani 1 1 d . U . . .
C1 C 0.9576(5) 0.4523(4) 0.8110(3) 0.0732(12) Uani 1 1 d . U . . .
H1A H 0.950220 0.434925 0.869288 0.088 Uiso 1 1 calc R U . . .
H1B H 1.049095 0.436765 0.793693 0.088 Uiso 1 1 calc R U . . .
C16 C 0.8589(5) 0.3820(4) 0.7614(4) 0.0882(15) Uani 1 1 d . U . . .
H16A H 0.903496 0.358454 0.711240 0.106 Uiso 1 1 calc R U . . .
H16B H 0.837953 0.319459 0.793890 0.106 Uiso 1 1 calc R U . . .
C42 C 1.0516(4) 0.6003(3) 0.6634(2) 0.0514(9) Uani 1 1 d . U . . .
C17 C 1.1754(4) 0.5424(4) 0.6908(3) 0.0725(13) Uani 1 1 d . U . . .
H17A H 1.168169 0.469029 0.675779 0.109 Uiso 1 1 calc R U . . .
H17B H 1.184427 0.548312 0.749776 0.109 Uiso 1 1 calc R U . . .
H17C H 1.253107 0.572862 0.664603 0.109 Uiso 1 1 calc R U . . .
C18 C 1.1482(4) 0.6151(4) 0.5258(3) 0.0704(12) Uani 1 1 d . U . . .
H18A H 1.234802 0.635608 0.548614 0.084 Uiso 1 1 calc R U . . .
H18B H 1.131741 0.658974 0.477577 0.084 Uiso 1 1 calc R U . . .
C19 C 1.1555(4) 0.5007(3) 0.4989(2) 0.0594(10) Uani 1 1 d . U . . .
C20 C 1.0497(5) 0.4315(3) 0.5076(3) 0.0664(11) Uani 1 1 d . U . . .
H20 H 0.970107 0.454548 0.532036 0.080 Uiso 1 1 calc R U . . .
C21 C 1.0601(5) 0.3273(4) 0.4802(3) 0.0731(12) Uani 1 1 d . U . . .
H21 H 0.988732 0.280396 0.487634 0.088 Uiso 1 1 calc R U . . .
C22 C 1.1759(6) 0.2940(4) 0.4421(3) 0.0778(14) Uani 1 1 d . U . . .
H22 H 1.183428 0.224550 0.423402 0.093 Uiso 1 1 calc R U . . .
C23 C 1.2795(6) 0.3626(4) 0.4318(3) 0.0901(16) Uani 1 1 d . U . . .
H23 H 1.357126 0.340219 0.404797 0.108 Uiso 1 1 calc R U . . .
C24 C 1.2714(5) 0.4649(4) 0.4607(3) 0.0807(14) Uani 1 1 d . U . . .
H24 H 1.344560 0.510380 0.454537 0.097 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.391(5) . ?
F2 B1 1.385(5) . ?
N1 C42 1.307(5) . ?
N1 C18 1.478(5) . ?
N1 B1 1.561(6) . ?
O1 C4 1.333(4) . ?
O1 B1 1.430(5) . ?
C11 C10 1.385(6) . ?
C11 C12 1.387(6) . ?
C12 C13 1.382(6) . ?
C13 C14 1.381(6) . ?
C13 C16 1.510(6) . ?
C14 C15 1.379(5) . ?
C15 C10 1.384(5) . ?
C10 C9 1.510(6) . ?
C9 C8 1.574(6) . ?
C8 C5 1.505(5) . ?
C5 C6 1.372(5) . ?
C5 C4 1.413(5) . ?
C6 C7 1.383(6) . ?
C7 C2 1.376(5) . ?
C2 C3 1.428(5) . ?
C2 C1 1.518(5) . ?
C3 C4 1.412(5) . ?
C3 C42 1.452(5) . ?
C1 C16 1.546(6) . ?
C42 C17 1.497(5) . ?
C18 C19 1.509(6) . ?
C19 C20 1.373(6) . ?
C19 C24 1.381(5) . ?
C20 C21 1.391(6) . ?
C21 C22 1.370(6) . ?
C22 C23 1.353(7) . ?
C23 C24 1.375(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C42 N1 C18 121.4(4) . . ?
C42 N1 B1 122.7(3) . . ?
C18 N1 B1 115.9(3) . . ?
C4 O1 B1 123.6(3) . . ?
F2 B1 F1 108.9(4) . . ?
F2 B1 O1 112.0(4) . . ?
F1 B1 O1 108.0(4) . . ?
F2 B1 N1 108.3(4) . . ?
F1 B1 N1 108.6(4) . . ?
O1 B1 N1 110.9(3) . . ?
C10 C11 C12 120.5(4) . . ?
C13 C12 C11 120.1(4) . . ?
C14 C13 C12 117.7(4) . . ?
C14 C13 C16 119.8(5) . . ?
C12 C13 C16 121.1(5) . . ?
C15 C14 C13 121.1(4) . . ?
C14 C15 C10 120.0(4) . . ?
C15 C10 C11 117.7(4) . . ?
C15 C10 C9 120.6(4) . . ?
C11 C10 C9 120.0(4) . . ?
C10 C9 C8 112.7(3) . . ?
C5 C8 C9 113.1(3) . . ?
C6 C5 C4 115.5(4) . . ?
C6 C5 C8 122.3(4) . . ?
C4 C5 C8 121.3(3) . . ?
C5 C6 C7 122.2(4) . . ?
C2 C7 C6 121.9(4) . . ?
C7 C2 C3 116.5(4) . . ?
C7 C2 C1 117.3(4) . . ?
C3 C2 C1 123.5(4) . . ?
C4 C3 C2 118.2(3) . . ?
C4 C3 C42 118.4(3) . . ?
C2 C3 C42 123.4(3) . . ?
O1 C4 C3 121.3(3) . . ?
O1 C4 C5 116.7(3) . . ?
C3 C4 C5 122.1(3) . . ?
C2 C1 C16 112.6(4) . . ?
C13 C16 C1 114.2(4) . . ?
N1 C42 C3 119.4(3) . . ?
N1 C42 C17 120.3(4) . . ?
C3 C42 C17 120.1(4) . . ?
N1 C18 C19 113.9(3) . . ?
C20 C19 C24 118.4(4) . . ?
C20 C19 C18 122.8(4) . . ?
C24 C19 C18 118.8(4) . . ?
C19 C20 C21 120.8(4) . . ?
C22 C21 C20 119.6(5) . . ?
C23 C22 C21 119.8(5) . . ?
C22 C23 C24 120.9(5) . . ?
C23 C24 C19 120.4(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O1 B1 F2 101.6(4) . . . . ?
C4 O1 B1 F1 -138.5(4) . . . . ?
C4 O1 B1 N1 -19.6(5) . . . . ?
C42 N1 B1 F2 -108.4(4) . . . . ?
C18 N1 B1 F2 72.3(4) . . . . ?
C42 N1 B1 F1 133.5(4) . . . . ?
C18 N1 B1 F1 -45.8(5) . . . . ?
C42 N1 B1 O1 14.9(5) . . . . ?
C18 N1 B1 O1 -164.4(3) . . . . ?
C10 C11 C12 C13 -0.9(6) . . . . ?
C11 C12 C13 C14 -12.6(6) . . . . ?
C11 C12 C13 C16 154.3(4) . . . . ?
C12 C13 C14 C15 12.6(6) . . . . ?
C16 C13 C14 C15 -154.4(4) . . . . ?
C13 C14 C15 C10 0.9(6) . . . . ?
C14 C15 C10 C11 -14.4(6) . . . . ?
C14 C15 C10 C9 150.6(4) . . . . ?
C12 C11 C10 C15 14.4(6) . . . . ?
C12 C11 C10 C9 -150.7(4) . . . . ?
C15 C10 C9 C8 -81.8(5) . . . . ?
C11 C10 C9 C8 82.9(5) . . . . ?
C10 C9 C8 C5 -3.3(5) . . . . ?
C9 C8 C5 C6 -85.3(5) . . . . ?
C9 C8 C5 C4 83.7(4) . . . . ?
C4 C5 C6 C7 -15.5(6) . . . . ?
C8 C5 C6 C7 154.1(4) . . . . ?
C5 C6 C7 C2 4.4(7) . . . . ?
C6 C7 C2 C3 13.4(6) . . . . ?
C6 C7 C2 C1 -148.6(4) . . . . ?
C7 C2 C3 C4 -18.9(5) . . . . ?
C1 C2 C3 C4 141.8(4) . . . . ?
C7 C2 C3 C42 161.2(4) . . . . ?
C1 C2 C3 C42 -38.1(6) . . . . ?
B1 O1 C4 C3 8.4(5) . . . . ?
B1 O1 C4 C5 -169.9(4) . . . . ?
C2 C3 C4 O1 -170.3(3) . . . . ?
C42 C3 C4 O1 9.6(5) . . . . ?
C2 C3 C4 C5 7.9(5) . . . . ?
C42 C3 C4 C5 -172.1(3) . . . . ?
C6 C5 C4 O1 -172.5(3) . . . . ?
C8 C5 C4 O1 17.8(5) . . . . ?
C6 C5 C4 C3 9.2(5) . . . . ?
C8 C5 C4 C3 -160.5(3) . . . . ?
C7 C2 C1 C16 96.2(5) . . . . ?
C3 C2 C1 C16 -64.4(6) . . . . ?
C14 C13 C16 C1 100.3(5) . . . . ?
C12 C13 C16 C1 -66.4(6) . . . . ?
C2 C1 C16 C13 -21.5(6) . . . . ?
C18 N1 C42 C3 -179.9(3) . . . . ?
B1 N1 C42 C3 0.9(6) . . . . ?
C18 N1 C42 C17 4.7(6) . . . . ?
B1 N1 C42 C17 -174.5(4) . . . . ?
C4 C3 C42 N1 -13.7(5) . . . . ?
C2 C3 C42 N1 166.2(3) . . . . ?
C4 C3 C42 C17 161.7(4) . . . . ?
C2 C3 C42 C17 -18.3(6) . . . . ?
C42 N1 C18 C19 68.9(5) . . . . ?
B1 N1 C18 C19 -111.8(4) . . . . ?
N1 C18 C19 C20 21.3(6) . . . . ?
N1 C18 C19 C24 -161.6(4) . . . . ?
C24 C19 C20 C21 1.4(7) . . . . ?
C18 C19 C20 C21 178.5(4) . . . . ?
C19 C20 C21 C22 -1.8(7) . . . . ?
C20 C21 C22 C23 0.3(7) . . . . ?
C21 C22 C23 C24 1.5(8) . . . . ?
C22 C23 C24 C19 -1.9(8) . . . . ?
C20 C19 C24 C23 0.4(7) . . . . ?
C18 C19 C24 C23 -176.9(5) . . . . ?

_refine_diff_density_max         0.144
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.034



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_12325
_database_code_depnum_ccdc_archive 'CCDC 2068952'
_audit_update_record             
;
2021-08-06 deposited with the CCDC.	2021-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H29 B F N O2'
_chemical_formula_weight         393.29

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'
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'
F F 0.0727 0.0534 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   11.2440(8)
_cell_length_b                   11.5352(6)
_cell_length_c                   15.7945(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2048.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1968
_cell_measurement_theta_min      4.7410
_cell_measurement_theta_max      71.0870

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.683
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83183
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4767
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.747
_diffrn_reflns_theta_max         67.248
_diffrn_reflns_theta_full        67.248
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_point_group_measured_fraction_full 0.858
_reflns_number_total             3147
_reflns_number_gt                2649
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.510
_reflns_Friedel_fraction_max     0.677
_reflns_Friedel_fraction_full    0.678

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0395P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 710 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.17(18)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3147
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.4730(3) 0.7968(3) 0.8049(3) 0.0370(9) Uani 1 1 d . . . . .
C1 C 0.0603(3) 0.6757(3) 0.7026(3) 0.0493(10) Uani 1 1 d . . . . .
H1A H -0.012183 0.630165 0.704215 0.059 Uiso 1 1 calc R U . . .
H1B H 0.105944 0.650490 0.653832 0.059 Uiso 1 1 calc R U . . .
C2 C 0.1317(3) 0.6514(3) 0.7822(2) 0.0386(8) Uani 1 1 d . . . . .
C3 C 0.2545(3) 0.6781(2) 0.7899(2) 0.0325(7) Uani 1 1 d . . . . .
C4 C 0.2986(3) 0.7138(3) 0.8696(2) 0.0345(7) Uani 1 1 d . . . . .
C5 C 0.2254(3) 0.7142(3) 0.9418(2) 0.0391(8) Uani 1 1 d . . . . .
C6 C 0.1171(3) 0.6605(3) 0.9347(3) 0.0464(10) Uani 1 1 d . . . . .
H6 H 0.074123 0.643686 0.983451 0.056 Uiso 1 1 calc R U . . .
C7 C 0.0698(3) 0.6304(3) 0.8557(3) 0.0466(9) Uani 1 1 d . . . . .
H7 H -0.004753 0.595678 0.852961 0.056 Uiso 1 1 calc R U . . .
C8 C 0.2525(4) 0.7921(4) 1.0166(2) 0.0507(10) Uani 1 1 d . . . . .
H8A H 0.335585 0.814638 1.014470 0.061 Uiso 1 1 calc R U . . .
H8B H 0.240166 0.748840 1.068534 0.061 Uiso 1 1 calc R U . . .
C9 C 0.1731(4) 0.9047(4) 1.0187(3) 0.0581(11) Uani 1 1 d . . . . .
H9A H 0.111032 0.895222 1.060770 0.070 Uiso 1 1 calc R U . . .
H9B H 0.221756 0.970284 1.035443 0.070 Uiso 1 1 calc R U . . .
C10 C 0.1169(4) 0.9299(3) 0.9339(2) 0.0426(9) Uani 1 1 d . . . . .
C11 C 0.0001(3) 0.8992(3) 0.9176(3) 0.0468(10) Uani 1 1 d . . . . .
H11 H -0.054492 0.895992 0.961819 0.056 Uiso 1 1 calc R U . . .
C12 C -0.0361(4) 0.8733(3) 0.8360(3) 0.0479(10) Uani 1 1 d . . . . .
H12 H -0.114924 0.853099 0.825967 0.057 Uiso 1 1 calc R U . . .
C13 C 0.0428(4) 0.8771(3) 0.7694(2) 0.0443(9) Uani 1 1 d . . . . .
C14 C 0.1522(3) 0.9301(3) 0.7842(2) 0.0414(9) Uani 1 1 d . . . . .
H14 H 0.201724 0.947447 0.738774 0.050 Uiso 1 1 calc R U . . .
C15 C 0.1882(3) 0.9570(3) 0.8652(2) 0.0437(9) Uani 1 1 d . . . . .
H15 H 0.260848 0.993581 0.873826 0.052 Uiso 1 1 calc R U . . .
C16 C 0.0269(4) 0.8050(3) 0.6907(3) 0.0625(12) Uani 1 1 d . . . . .
H16A H 0.075617 0.837420 0.645897 0.075 Uiso 1 1 calc R U . . .
H16B H -0.055456 0.809880 0.672774 0.075 Uiso 1 1 calc R U . . .
C17 C 0.3387(3) 0.6637(3) 0.7216(2) 0.0316(7) Uani 1 1 d . . . . .
C18 C 0.3182(3) 0.5726(3) 0.6555(2) 0.0417(9) Uani 1 1 d . . . . .
H18A H 0.319853 0.607749 0.600389 0.063 Uiso 1 1 calc R U . . .
H18B H 0.242111 0.536985 0.664556 0.063 Uiso 1 1 calc R U . . .
H18C H 0.379475 0.514917 0.659154 0.063 Uiso 1 1 calc R U . . .
C19 C 0.6395(3) 0.7015(3) 0.7490(2) 0.0432(9) Uani 1 1 d . . . . .
H19A H 0.645844 0.626213 0.775949 0.052 Uiso 1 1 calc R U . . .
H19B H 0.717147 0.722915 0.727194 0.052 Uiso 1 1 calc R U . . .
C20 C 0.5480(3) 0.6972(3) 0.6766(2) 0.0346(7) Uani 1 1 d . . . . .
H20 H 0.544298 0.618181 0.653954 0.042 Uiso 1 1 calc R U . . .
C21 C 0.5713(3) 0.7831(3) 0.6029(2) 0.0418(8) Uani 1 1 d . . . . .
C22 C 0.6040(4) 0.9060(3) 0.6313(3) 0.0657(13) Uani 1 1 d . . . . .
H22A H 0.619043 0.953313 0.582475 0.098 Uiso 1 1 calc R U . . .
H22B H 0.674026 0.903212 0.666024 0.098 Uiso 1 1 calc R U . . .
H22C H 0.539438 0.938483 0.663237 0.098 Uiso 1 1 calc R U . . .
C23 C 0.6741(4) 0.7336(4) 0.5508(3) 0.0634(12) Uani 1 1 d . . . . .
H23A H 0.652391 0.658496 0.529563 0.095 Uiso 1 1 calc R U . . .
H23B H 0.743394 0.726646 0.585930 0.095 Uiso 1 1 calc R U . . .
H23C H 0.690946 0.784401 0.504210 0.095 Uiso 1 1 calc R U . . .
C24 C 0.4620(4) 0.7901(4) 0.5456(2) 0.0574(11) Uani 1 1 d . . . . .
H24A H 0.478200 0.841418 0.499120 0.086 Uiso 1 1 calc R U . . .
H24B H 0.395595 0.818981 0.577381 0.086 Uiso 1 1 calc R U . . .
H24C H 0.443717 0.714283 0.524173 0.086 Uiso 1 1 calc R U . . .
F1 F 0.43854(18) 0.91212(15) 0.79356(14) 0.0468(5) Uani 1 1 d . . . . .
N1 N 0.4392(2) 0.7207(2) 0.72586(16) 0.0308(6) Uani 1 1 d . . . . .
O2 O 0.5992(2) 0.7855(2) 0.80790(15) 0.0427(6) Uani 1 1 d . . . . .
O1 O 0.4117(2) 0.7502(2) 0.87806(14) 0.0399(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 F1 1.397(4) . ?
B1 O2 1.426(4) . ?
B1 O1 1.449(4) . ?
B1 N1 1.572(4) . ?
C1 C2 1.518(5) . ?
C1 C16 1.549(5) . ?
C2 C7 1.376(5) . ?
C2 C3 1.420(4) . ?
C3 C4 1.415(4) . ?
C3 C17 1.444(4) . ?
C4 O1 1.346(4) . ?
C4 C5 1.407(4) . ?
C5 C6 1.371(5) . ?
C5 C8 1.515(5) . ?
C6 C7 1.400(5) . ?
C8 C9 1.577(5) . ?
C9 C10 1.509(5) . ?
C10 C11 1.384(5) . ?
C10 C15 1.384(5) . ?
C11 C12 1.385(5) . ?
C12 C13 1.377(5) . ?
C13 C14 1.394(5) . ?
C13 C16 1.506(5) . ?
C14 C15 1.377(5) . ?
C17 N1 1.309(4) . ?
C17 C18 1.499(4) . ?
C19 O2 1.418(4) . ?
C19 C20 1.540(4) . ?
C20 N1 1.475(4) . ?
C20 C21 1.550(4) . ?
C21 C24 1.528(5) . ?
C21 C23 1.530(5) . ?
C21 C22 1.531(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 B1 O2 111.6(3) . . ?
F1 B1 O1 108.9(3) . . ?
O2 B1 O1 114.3(3) . . ?
F1 B1 N1 111.3(3) . . ?
O2 B1 N1 102.4(3) . . ?
O1 B1 N1 108.1(3) . . ?
C2 C1 C16 114.0(3) . . ?
C7 C2 C3 117.2(3) . . ?
C7 C2 C1 117.7(3) . . ?
C3 C2 C1 123.0(3) . . ?
C4 C3 C2 118.7(3) . . ?
C4 C3 C17 117.9(3) . . ?
C2 C3 C17 123.3(3) . . ?
O1 C4 C5 118.1(3) . . ?
O1 C4 C3 120.7(3) . . ?
C5 C4 C3 121.2(3) . . ?
C6 C5 C4 116.9(3) . . ?
C6 C5 C8 120.7(3) . . ?
C4 C5 C8 121.1(3) . . ?
C5 C6 C7 121.5(3) . . ?
C2 C7 C6 121.1(3) . . ?
C5 C8 C9 113.0(3) . . ?
C10 C9 C8 112.2(3) . . ?
C11 C10 C15 117.5(4) . . ?
C11 C10 C9 120.9(4) . . ?
C15 C10 C9 119.7(4) . . ?
C10 C11 C12 120.4(4) . . ?
C13 C12 C11 121.0(4) . . ?
C12 C13 C14 117.0(3) . . ?
C12 C13 C16 122.5(4) . . ?
C14 C13 C16 119.0(4) . . ?
C15 C14 C13 120.9(4) . . ?
C14 C15 C10 120.5(4) . . ?
C13 C16 C1 113.8(3) . . ?
N1 C17 C3 118.0(3) . . ?
N1 C17 C18 121.3(3) . . ?
C3 C17 C18 120.0(3) . . ?
O2 C19 C20 107.2(3) . . ?
N1 C20 C19 99.0(2) . . ?
N1 C20 C21 114.8(3) . . ?
C19 C20 C21 115.1(3) . . ?
C24 C21 C23 107.9(3) . . ?
C24 C21 C22 108.5(3) . . ?
C23 C21 C22 108.8(3) . . ?
C24 C21 C20 110.0(3) . . ?
C23 C21 C20 107.0(3) . . ?
C22 C21 C20 114.4(3) . . ?
C17 N1 C20 126.6(3) . . ?
C17 N1 B1 121.9(3) . . ?
C20 N1 B1 108.8(3) . . ?
C19 O2 B1 111.0(3) . . ?
C4 O1 B1 119.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 C1 C2 C7 87.1(4) . . . . ?
C16 C1 C2 C3 -76.1(5) . . . . ?
C7 C2 C3 C4 -17.7(4) . . . . ?
C1 C2 C3 C4 145.6(3) . . . . ?
C7 C2 C3 C17 158.3(3) . . . . ?
C1 C2 C3 C17 -38.4(5) . . . . ?
C2 C3 C4 O1 -173.9(3) . . . . ?
C17 C3 C4 O1 10.0(4) . . . . ?
C2 C3 C4 C5 5.1(5) . . . . ?
C17 C3 C4 C5 -171.1(3) . . . . ?
O1 C4 C5 C6 -170.2(3) . . . . ?
C3 C4 C5 C6 10.8(5) . . . . ?
O1 C4 C5 C8 22.9(5) . . . . ?
C3 C4 C5 C8 -156.1(3) . . . . ?
C4 C5 C6 C7 -14.3(5) . . . . ?
C8 C5 C6 C7 152.7(3) . . . . ?
C3 C2 C7 C6 14.7(5) . . . . ?
C1 C2 C7 C6 -149.5(3) . . . . ?
C5 C6 C7 C2 1.5(5) . . . . ?
C6 C5 C8 C9 -65.5(4) . . . . ?
C4 C5 C8 C9 100.9(4) . . . . ?
C5 C8 C9 C10 -18.2(5) . . . . ?
C8 C9 C10 C11 99.4(4) . . . . ?
C8 C9 C10 C15 -64.5(5) . . . . ?
C15 C10 C11 C12 13.1(5) . . . . ?
C9 C10 C11 C12 -151.1(4) . . . . ?
C10 C11 C12 C13 0.2(5) . . . . ?
C11 C12 C13 C14 -12.7(5) . . . . ?
C11 C12 C13 C16 153.3(3) . . . . ?
C12 C13 C14 C15 12.1(5) . . . . ?
C16 C13 C14 C15 -154.4(3) . . . . ?
C13 C14 C15 C10 1.2(5) . . . . ?
C11 C10 C15 C14 -13.8(5) . . . . ?
C9 C10 C15 C14 150.7(3) . . . . ?
C12 C13 C16 C1 -76.3(5) . . . . ?
C14 C13 C16 C1 89.4(5) . . . . ?
C2 C1 C16 C13 -14.9(6) . . . . ?
C4 C3 C17 N1 -23.7(4) . . . . ?
C2 C3 C17 N1 160.3(3) . . . . ?
C4 C3 C17 C18 147.3(3) . . . . ?
C2 C3 C17 C18 -28.6(5) . . . . ?
O2 C19 C20 N1 -33.8(3) . . . . ?
O2 C19 C20 C21 89.0(3) . . . . ?
N1 C20 C21 C24 -53.6(4) . . . . ?
C19 C20 C21 C24 -167.5(3) . . . . ?
N1 C20 C21 C23 -170.6(3) . . . . ?
C19 C20 C21 C23 75.5(4) . . . . ?
N1 C20 C21 C22 68.9(4) . . . . ?
C19 C20 C21 C22 -45.1(4) . . . . ?
C3 C17 N1 C20 163.2(3) . . . . ?
C18 C17 N1 C20 -7.7(5) . . . . ?
C3 C17 N1 B1 3.9(4) . . . . ?
C18 C17 N1 B1 -167.0(3) . . . . ?
C19 C20 N1 C17 -132.7(3) . . . . ?
C21 C20 N1 C17 104.2(4) . . . . ?
C19 C20 N1 B1 28.8(3) . . . . ?
C21 C20 N1 B1 -94.2(3) . . . . ?
F1 B1 N1 C17 -92.9(4) . . . . ?
O2 B1 N1 C17 147.7(3) . . . . ?
O1 B1 N1 C17 26.7(4) . . . . ?
F1 B1 N1 C20 104.5(3) . . . . ?
O2 B1 N1 C20 -14.9(3) . . . . ?
O1 B1 N1 C20 -135.9(3) . . . . ?
C20 C19 O2 B1 27.1(4) . . . . ?
F1 B1 O2 C19 -127.1(3) . . . . ?
O1 B1 O2 C19 108.8(3) . . . . ?
N1 B1 O2 C19 -7.9(4) . . . . ?
C5 C4 O1 B1 -154.3(3) . . . . ?
C3 C4 O1 B1 24.7(4) . . . . ?
F1 B1 O1 C4 80.6(4) . . . . ?
O2 B1 O1 C4 -153.9(3) . . . . ?
N1 B1 O1 C4 -40.5(4) . . . . ?

_refine_diff_density_max         0.160
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.034



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Sp-3b
_database_code_depnum_ccdc_archive 'CCDC 2068950'
_audit_update_record             
;
2021-08-06 deposited with the CCDC.	2021-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H24 B F2 N O'
_chemical_formula_weight         403.26

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'
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'
F F 0.0727 0.0534 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   9.9193(11)
_cell_length_b                   12.6175(11)
_cell_length_c                   16.1730(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2024.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1029
_cell_measurement_theta_min      4.3950
_cell_measurement_theta_max      68.5080

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.747
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.74929
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1281
_diffrn_reflns_number            4903
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.445
_diffrn_reflns_theta_max         67.235
_diffrn_reflns_theta_full        67.235
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_point_group_measured_fraction_full 0.877
_reflns_number_total             3192
_reflns_number_gt                2276
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.535
_reflns_Friedel_fraction_max     0.715
_reflns_Friedel_fraction_full    0.715

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0032(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 577 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3192
_refine_ls_number_parameters     273
_refine_ls_number_restraints     1044
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1310
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      0.954
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.3431(4) 0.3544(3) 0.50524(19) 0.0785(10) Uani 1 1 d . U . . .
F2 F 0.4722(4) 0.2075(3) 0.5146(2) 0.0846(11) Uani 1 1 d . U . . .
N1 N 0.5421(4) 0.3629(3) 0.5881(3) 0.0524(10) Uani 1 1 d . U . . .
O1 O 0.3458(4) 0.2548(2) 0.62623(19) 0.0526(8) Uani 1 1 d . U . . .
B1 B 0.4213(7) 0.2929(5) 0.5574(4) 0.0575(14) Uani 1 1 d . U . . .
C12 C 0.1360(6) 0.5329(4) 0.7980(4) 0.0653(14) Uani 1 1 d . U . . .
H12 H 0.133419 0.568027 0.848528 0.078 Uiso 1 1 calc R U . . .
C11 C 0.0482(6) 0.4500(4) 0.7828(3) 0.0612(13) Uani 1 1 d . U . . .
H11 H -0.014499 0.430679 0.822789 0.073 Uiso 1 1 calc R U . . .
C10 C 0.0527(5) 0.3957(4) 0.7085(3) 0.0525(11) Uani 1 1 d . U . . .
C15 C 0.1240(5) 0.4410(4) 0.6438(3) 0.0562(12) Uani 1 1 d . U . . .
H15 H 0.112717 0.415966 0.590198 0.067 Uiso 1 1 calc R U . . .
C14 C 0.2120(6) 0.5238(4) 0.6595(3) 0.0594(13) Uani 1 1 d . U . . .
H14 H 0.261124 0.552918 0.616121 0.071 Uiso 1 1 calc R U . . .
C13 C 0.2280(6) 0.5636(4) 0.7379(4) 0.0638(14) Uani 1 1 d . U . . .
C16 C 0.3589(7) 0.6183(5) 0.7619(4) 0.0833(18) Uani 1 1 d . U . . .
H16A H 0.337713 0.680178 0.795031 0.100 Uiso 1 1 calc R U . . .
H16B H 0.403652 0.642559 0.712081 0.100 Uiso 1 1 calc R U . . .
C1 C 0.4569(7) 0.5470(4) 0.8109(4) 0.0705(15) Uani 1 1 d . U . . .
H1A H 0.548351 0.562588 0.793521 0.085 Uiso 1 1 calc R U . . .
H1B H 0.449763 0.564213 0.869182 0.085 Uiso 1 1 calc R U . . .
C2 C 0.4306(5) 0.4295(4) 0.7996(3) 0.0539(12) Uani 1 1 d . U . . .
C3 C 0.4442(5) 0.3763(3) 0.7224(3) 0.0445(10) Uani 1 1 d . U . . .
C4 C 0.3499(5) 0.2975(3) 0.7017(3) 0.0442(10) Uani 1 1 d . U . . .
C5 C 0.2542(5) 0.2608(3) 0.7594(3) 0.0490(11) Uani 1 1 d . U . . .
C6 C 0.2698(6) 0.2956(4) 0.8392(3) 0.0580(13) Uani 1 1 d . U . . .
H6 H 0.223508 0.261347 0.881472 0.070 Uiso 1 1 calc R U . . .
C7 C 0.3526(6) 0.3801(4) 0.8584(3) 0.0609(13) Uani 1 1 d . U . . .
H7 H 0.355773 0.404253 0.912687 0.073 Uiso 1 1 calc R U . . .
C8 C 0.1281(6) 0.2036(4) 0.7319(4) 0.0607(14) Uani 1 1 d . U . . .
H8A H 0.096355 0.159193 0.776770 0.073 Uiso 1 1 calc R U . . .
H8B H 0.150250 0.157726 0.685705 0.073 Uiso 1 1 calc R U . . .
C9 C 0.0107(6) 0.2812(4) 0.7050(4) 0.0660(14) Uani 1 1 d . U . . .
H9A H -0.017029 0.264048 0.649035 0.079 Uiso 1 1 calc R U . . .
H9B H -0.066198 0.270478 0.741049 0.079 Uiso 1 1 calc R U . . .
C17 C 0.5517(5) 0.4000(4) 0.6638(3) 0.0495(11) Uani 1 1 d . U . . .
C18 C 0.6761(6) 0.4577(5) 0.6906(4) 0.0703(16) Uani 1 1 d . U . . .
H18A H 0.753782 0.425372 0.665714 0.105 Uiso 1 1 calc R U . . .
H18B H 0.683961 0.454171 0.749720 0.105 Uiso 1 1 calc R U . . .
H18C H 0.670385 0.530421 0.673644 0.105 Uiso 1 1 calc R U . . .
C19 C 0.6486(6) 0.3844(4) 0.5255(4) 0.0662(14) Uani 1 1 d . U . . .
H19A H 0.631750 0.340903 0.477161 0.079 Uiso 1 1 calc R U . . .
H19B H 0.735198 0.363560 0.548174 0.079 Uiso 1 1 calc R U . . .
C20 C 0.6561(6) 0.4993(4) 0.4991(3) 0.0572(12) Uani 1 1 d . U . . .
C21 C 0.5491(6) 0.5685(4) 0.5079(3) 0.0653(14) Uani 1 1 d . U . . .
H21 H 0.469430 0.545161 0.532167 0.078 Uiso 1 1 calc R U . . .
C22 C 0.5594(7) 0.6717(4) 0.4808(3) 0.0694(15) Uani 1 1 d . U . . .
H22 H 0.487753 0.718163 0.488705 0.083 Uiso 1 1 calc R U . . .
C23 C 0.6748(7) 0.7068(5) 0.4422(4) 0.0784(18) Uani 1 1 d . U . . .
H23 H 0.681639 0.776383 0.423804 0.094 Uiso 1 1 calc R U . . .
C24 C 0.7789(8) 0.6376(5) 0.4316(4) 0.088(2) Uani 1 1 d . U . . .
H24 H 0.856175 0.659707 0.403939 0.106 Uiso 1 1 calc R U . . .
C25 C 0.7713(7) 0.5352(5) 0.4611(4) 0.0768(17) Uani 1 1 d . U . . .
H25 H 0.844794 0.490086 0.455313 0.092 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.383(7) . ?
F2 B1 1.376(7) . ?
N1 C17 1.314(6) . ?
N1 C19 1.488(6) . ?
N1 B1 1.569(8) . ?
O1 C4 1.334(5) . ?
O1 B1 1.426(7) . ?
C12 C11 1.383(8) . ?
C12 C13 1.389(8) . ?
C11 C10 1.383(7) . ?
C10 C15 1.386(7) . ?
C10 C9 1.505(7) . ?
C15 C14 1.384(7) . ?
C14 C13 1.373(8) . ?
C13 C16 1.521(8) . ?
C16 C1 1.543(8) . ?
C1 C2 1.516(7) . ?
C2 C7 1.376(7) . ?
C2 C3 1.424(7) . ?
C3 C4 1.406(6) . ?
C3 C17 1.458(7) . ?
C4 C5 1.409(7) . ?
C5 C6 1.372(7) . ?
C5 C8 1.511(7) . ?
C6 C7 1.381(8) . ?
C8 C9 1.582(7) . ?
C17 C18 1.497(7) . ?
C19 C20 1.514(7) . ?
C20 C25 1.374(8) . ?
C20 C21 1.381(8) . ?
C21 C22 1.378(7) . ?
C22 C23 1.377(9) . ?
C23 C24 1.363(9) . ?
C24 C25 1.379(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 N1 C19 121.1(5) . . ?
C17 N1 B1 123.4(4) . . ?
C19 N1 B1 115.4(4) . . ?
C4 O1 B1 124.2(4) . . ?
F2 B1 F1 109.8(5) . . ?
F2 B1 O1 108.7(5) . . ?
F1 B1 O1 111.8(5) . . ?
F2 B1 N1 108.6(5) . . ?
F1 B1 N1 107.8(4) . . ?
O1 B1 N1 110.1(4) . . ?
C11 C12 C13 120.0(5) . . ?
C12 C11 C10 120.6(6) . . ?
C11 C10 C15 117.9(5) . . ?
C11 C10 C9 120.0(5) . . ?
C15 C10 C9 120.5(5) . . ?
C14 C15 C10 119.6(5) . . ?
C13 C14 C15 121.2(5) . . ?
C14 C13 C12 118.0(5) . . ?
C14 C13 C16 120.1(6) . . ?
C12 C13 C16 120.6(6) . . ?
C13 C16 C1 113.9(5) . . ?
C2 C1 C16 113.6(5) . . ?
C7 C2 C3 116.4(5) . . ?
C7 C2 C1 117.2(5) . . ?
C3 C2 C1 123.4(5) . . ?
C4 C3 C2 118.7(5) . . ?
C4 C3 C17 118.5(4) . . ?
C2 C3 C17 122.9(4) . . ?
O1 C4 C3 121.6(4) . . ?
O1 C4 C5 116.9(4) . . ?
C3 C4 C5 121.5(4) . . ?
C6 C5 C4 116.3(5) . . ?
C6 C5 C8 121.5(5) . . ?
C4 C5 C8 121.3(4) . . ?
C5 C6 C7 121.7(5) . . ?
C2 C7 C6 121.9(5) . . ?
C5 C8 C9 113.3(4) . . ?
C10 C9 C8 112.3(4) . . ?
N1 C17 C3 118.7(5) . . ?
N1 C17 C18 120.2(5) . . ?
C3 C17 C18 120.9(4) . . ?
N1 C19 C20 113.7(4) . . ?
C25 C20 C21 118.5(5) . . ?
C25 C20 C19 118.8(5) . . ?
C21 C20 C19 122.6(5) . . ?
C22 C21 C20 120.5(6) . . ?
C23 C22 C21 120.6(6) . . ?
C24 C23 C22 118.8(6) . . ?
C23 C24 C25 120.9(6) . . ?
C20 C25 C24 120.6(7) . . ?

_refine_diff_density_max         0.137
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.035



