# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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-BF2
_audit_block_doi                 10.5517/ccdc.csd.cc2f7483
_database_code_depnum_ccdc_archive 'CCDC 2241184'
loop_
_audit_author_name
_audit_author_address
'Ramkumar Kannan'
;Tata Institute of Fundamental Research Hyderabad
India
;
_audit_update_record             
;
2023-05-08 deposited with the CCDC.	2023-10-20 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         'C23 H27 B F2 N2'
_chemical_formula_sum            'C23 H27 B F2 N2'
_chemical_formula_weight         380.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   12.9281(5)
_cell_length_b                   12.2645(4)
_cell_length_c                   13.2506(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.120(4)
_cell_angle_gamma                90
_cell_volume                     2092.59(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5862
_cell_measurement_theta_min      3.0810
_cell_measurement_theta_max      26.7990

_exptl_crystal_description       Cube
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_F_000             808.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.61499
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19482
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.842
_diffrn_reflns_theta_max         30.456
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.886
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.886
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6378
_reflns_number_gt                3670
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1026P)²+0.3285P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5648
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1998
_refine_ls_wR_factor_gt          0.1818
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.43768(10) 0.27419(11) 0.50967(10) 0.0848(4) Uani 1 1 d . . . . .
F2 F 0.32336(12) 0.20537(9) 0.61021(12) 0.0886(5) Uani 1 1 d . . . . .
N2 N 0.27227(11) 0.37770(10) 0.52005(10) 0.0449(3) Uani 1 1 d . . . . .
N1 N 0.38027(11) 0.39589(11) 0.64350(11) 0.0463(4) Uani 1 1 d . . . . .
C15 C 0.19205(11) 0.57632(12) 0.68695(12) 0.0384(3) Uani 1 1 d . . . . .
C2 C 0.26235(12) 0.55940(12) 0.61016(11) 0.0378(3) Uani 1 1 d . . . . .
C1 C 0.30278(12) 0.44821(12) 0.59213(11) 0.0359(3) Uani 1 1 d . . . . .
C9 C 0.19290(12) 0.77375(13) 0.64588(12) 0.0416(4) Uani 1 1 d . . . . .
C10 C 0.15743(12) 0.68439(13) 0.70523(12) 0.0411(4) Uani 1 1 d . . . . .
C4 C 0.26120(13) 0.75320(12) 0.57120(12) 0.0420(4) Uani 1 1 d . . . . .
C3 C 0.29422(14) 0.64412(12) 0.55530(12) 0.0432(4) Uani 1 1 d . . . . .
H3 H 0.339103 0.630755 0.505624 0.052 Uiso 1 1 calc R U . . .
C14 C 0.15878(13) 0.48958(14) 0.74534(13) 0.0478(4) Uani 1 1 d . . . . .
H14 H 0.180875 0.419077 0.732894 0.057 Uiso 1 1 calc R U . . .
C16 C 0.46615(13) 0.43251(15) 0.71586(13) 0.0485(4) Uani 1 1 d . . . . .
C20 C 0.17671(14) 0.36483(14) 0.45292(14) 0.0502(4) Uani 1 1 d . . . . .
C5 C 0.29970(17) 0.84038(14) 0.51616(14) 0.0548(5) Uani 1 1 d . . . . .
H5 H 0.344481 0.826210 0.466573 0.066 Uiso 1 1 calc R U . . .
C8 C 0.16466(15) 0.88369(14) 0.66154(16) 0.0565(5) Uani 1 1 d . . . . .
H8 H 0.118341 0.899744 0.709260 0.068 Uiso 1 1 calc R U . . .
C11 C 0.09068(15) 0.69855(17) 0.78255(15) 0.0572(5) Uani 1 1 d . . . . .
H11 H 0.066543 0.768042 0.795920 0.069 Uiso 1 1 calc R U . . .
C13 C 0.09432(15) 0.50729(18) 0.82030(15) 0.0597(5) Uani 1 1 d . . . . .
H13 H 0.073313 0.449270 0.858785 0.072 Uiso 1 1 calc R U . . .
C7 C 0.20416(17) 0.96630(15) 0.60794(17) 0.0662(6) Uani 1 1 d . . . . .
H7 H 0.185292 1.037838 0.620620 0.079 Uiso 1 1 calc R U . . .
C6 C 0.27192(18) 0.94566(15) 0.53489(17) 0.0640(5) Uani 1 1 d . . . . .
H6 H 0.298295 1.002851 0.498892 0.077 Uiso 1 1 calc R U . . .
C12 C 0.06055(16) 0.6122(2) 0.83848(16) 0.0662(6) Uani 1 1 d . . . . .
H12 H 0.016795 0.624024 0.889420 0.079 Uiso 1 1 calc R U . . .
B1 B 0.35985(17) 0.29676(15) 0.56834(17) 0.0515(5) Uani 1 1 d . . . . .
C21 C 0.1355(2) 0.47184(19) 0.4104(2) 0.0872(8) Uani 1 1 d . . . . .
H21A H 0.073147 0.459248 0.367103 0.131 Uiso 1 1 calc R U . . .
H21B H 0.120657 0.519181 0.464986 0.131 Uiso 1 1 calc R U . . .
H21C H 0.186611 0.505288 0.372118 0.131 Uiso 1 1 calc R U . . .
C24 C 0.2039(2) 0.2921(3) 0.3667(2) 0.1025(10) Uani 1 1 d . . . . .
H24A H 0.143325 0.281201 0.320361 0.154 Uiso 1 1 calc R U . . .
H24B H 0.257329 0.326030 0.331776 0.154 Uiso 1 1 calc R U . . .
H24C H 0.228194 0.222986 0.393264 0.154 Uiso 1 1 calc R U . . .
C17 C 0.5338(2) 0.5127(2) 0.6638(2) 0.0930(8) Uani 1 1 d . . . . .
H17A H 0.589863 0.536654 0.710924 0.140 Uiso 1 1 calc R U . . .
H17B H 0.561414 0.477636 0.607210 0.140 Uiso 1 1 calc R U . . .
H17C H 0.492757 0.574410 0.640249 0.140 Uiso 1 1 calc R U . . .
C22 C 0.0948(2) 0.3101(3) 0.5106(2) 0.1044(10) Uani 1 1 d . . . . .
H22A H 0.032097 0.301551 0.466780 0.157 Uiso 1 1 calc R U . . .
H22B H 0.119383 0.239776 0.533821 0.157 Uiso 1 1 calc R U . . .
H22C H 0.081140 0.354268 0.567720 0.157 Uiso 1 1 calc R U . . .
C18 C 0.4287(2) 0.4855(3) 0.80786(19) 0.1040(11) Uani 1 1 d . . . . .
H18A H 0.487258 0.507918 0.852693 0.156 Uiso 1 1 calc R U . . .
H18B H 0.387168 0.547975 0.787745 0.156 Uiso 1 1 calc R U . . .
H18C H 0.387686 0.434398 0.842063 0.156 Uiso 1 1 calc R U . . .
C19 C 0.5310(3) 0.3320(2) 0.7441(3) 0.1269(14) Uani 1 1 d . . . . .
H19A H 0.588456 0.351841 0.791547 0.190 Uiso 1 1 calc R U . . .
H19B H 0.488944 0.278780 0.774356 0.190 Uiso 1 1 calc R U . . .
H19C H 0.556756 0.301848 0.684350 0.190 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 1.354(3) . ?
F2 B1 1.354(2) . ?
N2 C1 1.3223(19) . ?
N2 C20 1.465(2) . ?
N2 B1 1.596(2) . ?
N1 C1 1.3255(19) . ?
N1 C16 1.471(2) . ?
N1 B1 1.579(2) . ?
C15 C14 1.405(2) . ?
C15 C10 1.426(2) . ?
C15 C2 1.439(2) . ?
C2 C3 1.353(2) . ?
C2 C1 1.487(2) . ?
C1 B1 2.034(2) . ?
C9 C4 1.407(2) . ?
C9 C8 1.417(2) . ?
C9 C10 1.447(2) . ?
C10 C11 1.408(2) . ?
C4 C5 1.410(2) . ?
C4 C3 1.426(2) . ?
C14 C13 1.370(3) . ?
C16 C18 1.499(3) . ?
C16 C19 1.519(3) . ?
C16 C17 1.522(3) . ?
C20 C21 1.506(3) . ?
C20 C24 1.516(3) . ?
C20 C22 1.517(3) . ?
C5 C6 1.369(3) . ?
C8 C7 1.362(3) . ?
C11 C12 1.369(3) . ?
C13 C12 1.386(3) . ?
C7 C6 1.386(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 C20 133.64(14) . . ?
C1 N2 B1 87.82(12) . . ?
C20 N2 B1 134.91(13) . . ?
C1 N1 C16 132.75(14) . . ?
C1 N1 B1 88.43(12) . . ?
C16 N1 B1 136.08(14) . . ?
C14 C15 C10 119.60(14) . . ?
C14 C15 C2 121.60(14) . . ?
C10 C15 C2 118.79(14) . . ?
C3 C2 C15 120.74(14) . . ?
C3 C2 C1 119.30(14) . . ?
C15 C2 C1 119.94(13) . . ?
N2 C1 N1 102.56(13) . . ?
N2 C1 C2 128.99(14) . . ?
N1 C1 C2 128.44(14) . . ?
N2 C1 B1 51.66(10) . . ?
N1 C1 B1 50.91(10) . . ?
C2 C1 B1 179.27(14) . . ?
C4 C9 C8 117.36(16) . . ?
C4 C9 C10 119.73(14) . . ?
C8 C9 C10 122.87(16) . . ?
C11 C10 C15 117.40(16) . . ?
C11 C10 C9 123.13(15) . . ?
C15 C10 C9 119.47(14) . . ?
C9 C4 C5 120.05(15) . . ?
C9 C4 C3 119.15(15) . . ?
C5 C4 C3 120.73(16) . . ?
C2 C3 C4 122.11(15) . . ?
C13 C14 C15 121.01(17) . . ?
N1 C16 C18 112.49(16) . . ?
N1 C16 C19 106.32(17) . . ?
C18 C16 C19 111.2(2) . . ?
N1 C16 C17 109.41(16) . . ?
C18 C16 C17 109.2(2) . . ?
C19 C16 C17 108.0(2) . . ?
N2 C20 C21 112.56(16) . . ?
N2 C20 C24 106.35(16) . . ?
C21 C20 C24 109.2(2) . . ?
N2 C20 C22 109.30(17) . . ?
C21 C20 C22 109.6(2) . . ?
C24 C20 C22 109.8(2) . . ?
C6 C5 C4 120.74(19) . . ?
C7 C8 C9 121.19(19) . . ?
C12 C11 C10 121.38(18) . . ?
C14 C13 C12 119.64(18) . . ?
C8 C7 C6 121.20(17) . . ?
C5 C6 C7 119.44(19) . . ?
C11 C12 C13 120.97(17) . . ?
F2 B1 F1 111.72(16) . . ?
F2 B1 N1 115.07(17) . . ?
F1 B1 N1 115.37(17) . . ?
F2 B1 N2 114.74(17) . . ?
F1 B1 N2 115.72(17) . . ?
N1 B1 N2 81.18(11) . . ?
F2 B1 C1 123.24(16) . . ?
F1 B1 C1 125.04(15) . . ?
N1 B1 C1 40.66(8) . . ?
N2 B1 C1 40.52(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C15 C2 C3 -179.42(15) . . . . ?
C10 C15 C2 C3 -0.8(2) . . . . ?
C14 C15 C2 C1 -0.9(2) . . . . ?
C10 C15 C2 C1 177.73(14) . . . . ?
C20 N2 C1 N1 160.85(18) . . . . ?
B1 N2 C1 N1 0.82(14) . . . . ?
C20 N2 C1 C2 -20.4(3) . . . . ?
B1 N2 C1 C2 179.58(17) . . . . ?
C20 N2 C1 B1 160.0(2) . . . . ?
C16 N1 C1 N2 162.12(17) . . . . ?
B1 N1 C1 N2 -0.83(14) . . . . ?
C16 N1 C1 C2 -16.7(3) . . . . ?
B1 N1 C1 C2 -179.60(17) . . . . ?
C16 N1 C1 B1 162.9(2) . . . . ?
C3 C2 C1 N2 -80.8(2) . . . . ?
C15 C2 C1 N2 100.66(19) . . . . ?
C3 C2 C1 N1 97.7(2) . . . . ?
C15 C2 C1 N1 -80.9(2) . . . . ?
C14 C15 C10 C11 0.2(2) . . . . ?
C2 C15 C10 C11 -178.49(14) . . . . ?
C14 C15 C10 C9 179.20(14) . . . . ?
C2 C15 C10 C9 0.5(2) . . . . ?
C4 C9 C10 C11 178.77(15) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C4 C9 C10 C15 -0.2(2) . . . . ?
C8 C9 C10 C15 -177.99(16) . . . . ?
C8 C9 C4 C5 0.7(2) . . . . ?
C10 C9 C4 C5 -177.20(15) . . . . ?
C8 C9 C4 C3 177.99(16) . . . . ?
C10 C9 C4 C3 0.1(2) . . . . ?
C15 C2 C3 C4 0.7(3) . . . . ?
C1 C2 C3 C4 -177.84(15) . . . . ?
C9 C4 C3 C2 -0.3(3) . . . . ?
C5 C4 C3 C2 176.92(16) . . . . ?
C10 C15 C14 C13 -0.6(2) . . . . ?
C2 C15 C14 C13 178.00(15) . . . . ?
C1 N1 C16 C18 60.3(3) . . . . ?
B1 N1 C16 C18 -144.7(2) . . . . ?
C1 N1 C16 C19 -177.7(2) . . . . ?
B1 N1 C16 C19 -22.7(3) . . . . ?
C1 N1 C16 C17 -61.3(3) . . . . ?
B1 N1 C16 C17 93.7(2) . . . . ?
C1 N2 C20 C21 42.6(3) . . . . ?
B1 N2 C20 C21 -166.2(2) . . . . ?
C1 N2 C20 C24 162.1(2) . . . . ?
B1 N2 C20 C24 -46.7(3) . . . . ?
C1 N2 C20 C22 -79.4(3) . . . . ?
B1 N2 C20 C22 71.8(3) . . . . ?
C9 C4 C5 C6 0.4(3) . . . . ?
C3 C4 C5 C6 -176.81(19) . . . . ?
C4 C9 C8 C7 -1.5(3) . . . . ?
C10 C9 C8 C7 176.34(17) . . . . ?
C15 C10 C11 C12 0.4(3) . . . . ?
C9 C10 C11 C12 -178.62(17) . . . . ?
C15 C14 C13 C12 0.5(3) . . . . ?
C9 C8 C7 C6 1.2(3) . . . . ?
C4 C5 C6 C7 -0.8(3) . . . . ?
C8 C7 C6 C5 0.0(3) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C14 C13 C12 C11 0.0(3) . . . . ?
C1 N1 B1 F2 -112.59(17) . . . . ?
C16 N1 B1 F2 85.5(3) . . . . ?
C1 N1 B1 F1 115.03(17) . . . . ?
C16 N1 B1 F1 -46.9(3) . . . . ?
C1 N1 B1 N2 0.68(12) . . . . ?
C16 N1 B1 N2 -161.23(19) . . . . ?
C16 N1 B1 C1 -161.9(2) . . . . ?
C1 N2 B1 F2 112.94(17) . . . . ?
C20 N2 B1 F2 -46.6(3) . . . . ?
C1 N2 B1 F1 -114.67(17) . . . . ?
C20 N2 B1 F1 85.8(2) . . . . ?
C1 N2 B1 N1 -0.68(12) . . . . ?
C20 N2 B1 N1 -160.26(18) . . . . ?
C20 N2 B1 C1 -159.6(2) . . . . ?

_refine_diff_density_max         0.460
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.042

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

data_1-bf2
_database_code_depnum_ccdc_archive 'CCDC 2302135'
loop_
_audit_author_name
_audit_author_address
'Ramkumar Kannan'
;Tata Institute of Fundamental Research Hyderabad
India
;
_audit_update_record             
;
2023-10-19 deposited with the CCDC.	2023-10-20 downloaded from the CCDC.
;
_audit_creation_date             2023-10-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.182(C15 H23 B F2 N2)'
_chemical_formula_sum            'C15 H23 B F2 N2'
_chemical_formula_weight         280.16
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.9290(4)
_cell_length_b                   10.2818(4)
_cell_length_c                   13.9166(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1563.81(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6047
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7870
_cell_measurement_theta_min      2.7120
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9858
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.848
_diffrn_reflns_theta_min         2.720
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1381
_reflns_number_total             1647
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1647
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0507P)²+0.3826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1089
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Me refined with riding coordinates:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.58995(7) 0.95503(7) 0.70949(6) 0.0338(2) Uani 1 1 d . . . . .
N1 N 0.45291(9) 0.76314(9) 0.68481(8) 0.0226(3) Uani 1 1 d . . . . .
C1 C 0.500000 0.68198(17) 0.750000 0.0213(4) Uani 1 2 d S T P . .
C2 C 0.500000 0.53791(16) 0.750000 0.0233(4) Uani 1 2 d S T P . .
C6 C 0.43911(12) 0.74793(12) 0.57984(9) 0.0261(3) Uani 1 1 d . . . . .
C3 C 0.39092(13) 0.47070(13) 0.76317(10) 0.0296(3) Uani 1 1 d . . . . .
H3 H 0.317964 0.515827 0.771635 0.036 Uiso 1 1 calc R U . . .
C7 C 0.36216(13) 0.62915(13) 0.55495(10) 0.0336(3) Uani 1 1 d . . . . .
H7A H 0.354908 0.621966 0.486406 0.050 Uiso 1 1 calc R U . . .
H7B H 0.400830 0.552448 0.579953 0.050 Uiso 1 1 calc R U . . .
H7C H 0.282245 0.638146 0.582793 0.050 Uiso 1 1 calc R U . . .
C8 C 0.37429(13) 0.87076(14) 0.54562(11) 0.0349(4) Uani 1 1 d . . . . .
H8A H 0.362640 0.866517 0.477315 0.052 Uiso 1 1 calc R U . . .
H8B H 0.296224 0.877707 0.576817 0.052 Uiso 1 1 calc R U . . .
H8C H 0.423191 0.945415 0.561162 0.052 Uiso 1 1 calc R U . . .
C4 C 0.39176(15) 0.33582(15) 0.76357(11) 0.0392(4) Uani 1 1 d . . . . .
H4 H 0.319291 0.290154 0.773007 0.047 Uiso 1 1 calc R U . . .
C5 C 0.500000 0.2694(2) 0.750000 0.0436(6) Uani 1 2 d S T P . .
H5 H 0.500000 0.178950 0.750000 0.052 Uiso 1 2 calc R U P . .
C9 C 0.56559(14) 0.73714(16) 0.53420(11) 0.0388(4) Uani 1 1 d . . . . .
H9A H 0.557206 0.727226 0.465927 0.058 Uiso 1 1 calc R U . . .
H9B H 0.611699 0.814444 0.547817 0.058 Uiso 1 1 calc R U . . .
H9C H 0.607470 0.662956 0.560143 0.058 Uiso 1 1 calc R U . . .
B1 B 0.500000 0.87899(19) 0.750000 0.0258(4) Uani 1 2 d S T P . .


_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 1.3768(13) 3_656 ?
F1 B1 1.3768(13) . ?
N1 C1 1.3358(15) . ?
N1 C6 1.4769(16) . ?
N1 B1 1.5833(18) 3_656 ?
N1 B1 1.5833(18) . ?
C1 C2 1.481(2) . ?
C2 C3 1.3900(15) 3_656 ?
C2 C3 1.3900(15) . ?
C6 C7 1.5227(18) . ?
C6 C8 1.5243(18) . ?
C6 C9 1.5253(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.3869(19) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C5 1.3790(19) . ?
C5 H5 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
B1 B1 0.000(4) 3_656 ?

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
B1 F1 B1 0.00(14) 3_656 . ?
C1 N1 C6 130.16(10) . . ?
C1 N1 B1 87.45(10) . . ?
C1 N1 B1 87.45(10) . 3_656 ?
C6 N1 B1 132.82(9) . . ?
C6 N1 B1 132.82(9) . 3_656 ?
B1 N1 B1 0.00(9) 3_656 . ?
N1 C1 N1 102.67(14) 3_656 . ?
N1 C1 C2 128.66(7) 3_656 . ?
N1 C1 C2 128.66(7) . . ?
C3 C2 C1 119.81(8) . . ?
C3 C2 C1 119.81(8) 3_656 . ?
C3 C2 C3 120.38(17) 3_656 . ?
N1 C6 C7 111.49(11) . . ?
N1 C6 C8 105.59(10) . . ?
N1 C6 C9 109.08(11) . . ?
C7 C6 C8 109.68(11) . . ?
C7 C6 C9 110.33(12) . . ?
C8 C6 C9 110.57(11) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.47(14) . . ?
C4 C3 H3 120.3 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.02(15) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C4 120.63(19) . 3_656 ?
C4 C5 H5 119.7 3_656 . ?
C4 C5 H5 119.7 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
F1 B1 F1 110.80(15) . 3_656 ?
F1 B1 N1 115.13(6) . . ?
F1 B1 N1 115.13(6) 3_656 3_656 ?
F1 B1 N1 115.46(6) . 3_656 ?
F1 B1 N1 115.46(6) 3_656 . ?
N1 B1 N1 82.42(12) . 3_656 ?
B1 B1 F1 0(10) 3_656 . ?
B1 B1 F1 0(10) 3_656 3_656 ?
B1 B1 N1 0(10) 3_656 . ?
B1 B1 N1 0(10) 3_656 3_656 ?

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
N1 C1 C2 C3 -69.18(9) 3_656 . . 3_656 ?
N1 C1 C2 C3 110.82(9) 3_656 . . . ?
N1 C1 C2 C3 110.83(9) . . . 3_656 ?
N1 C1 C2 C3 -69.18(9) . . . . ?
C1 N1 C6 C7 58.63(16) . . . . ?
C1 N1 C6 C8 177.69(11) . . . . ?
C1 N1 C6 C9 -63.46(15) . . . . ?
C1 N1 B1 F1 -114.27(9) . . . 3_656 ?
C1 N1 B1 F1 114.61(9) . . . . ?
C1 N1 B1 N1 -0.001(0) . . . 3_656 ?
C1 N1 B1 B1 0(100) . . . 3_656 ?
C1 C2 C3 C4 -179.67(9) . . . . ?
C2 C3 C4 C5 -0.67(19) . . . . ?
C6 N1 C1 N1 148.51(14) . . . 3_656 ?
C6 N1 C1 C2 -31.49(14) . . . . ?
C6 N1 B1 F1 -32.42(16) . . . . ?
C6 N1 B1 F1 98.69(13) . . . 3_656 ?
C6 N1 B1 N1 -147.03(14) . . . 3_656 ?
C6 N1 B1 B1 0.0(4) . . . 3_656 ?
C3 C2 C3 C4 0.33(9) 3_656 . . . ?
C3 C4 C5 C4 0.34(10) . . . 3_656 ?
B1 F1 B1 F1 0(42) 3_656 . . 3_656 ?
B1 F1 B1 N1 0(72) 3_656 . . 3_656 ?
B1 F1 B1 N1 0(25) 3_656 . . . ?
B1 N1 C1 N1 0.001(1) 3_656 . . 3_656 ?
B1 N1 C1 N1 0.001(1) . . . 3_656 ?
B1 N1 C1 C2 180.000(1) . . . . ?
B1 N1 C1 C2 180.000(1) 3_656 . . . ?
B1 N1 C6 C7 -166.71(10) 3_656 . . . ?
B1 N1 C6 C7 -166.71(10) . . . . ?
B1 N1 C6 C8 -47.66(15) . . . . ?
B1 N1 C6 C8 -47.66(15) 3_656 . . . ?
B1 N1 C6 C9 71.19(15) . . . . ?
B1 N1 C6 C9 71.19(15) 3_656 . . . ?
B1 N1 B1 F1 0(14) 3_656 . . 3_656 ?
B1 N1 B1 F1 0(96) 3_656 . . . ?
B1 N1 B1 N1 0(100) 3_656 . . 3_656 ?

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

data_vc1001
_audit_block_doi                 10.5517/ccdc.csd.cc2g0bvp
_database_code_depnum_ccdc_archive 'CCDC 2264452'
loop_
_audit_author_name
_audit_author_address
'Ramkumar Kannan'
;Tata Institute of Fundamental Research Hyderabad
India
;
_audit_update_record             
;
2023-05-22 deposited with the CCDC.	2023-10-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_vc1001              
;
RESPONSE::The alert is genrated due to incompleteness of data, we have collected
 this data multiple times this is the best data we could obtain, after certain
  time the crystal quality starts degrading even in the liquid nitrogen flow. 
;
_vrf_PLAT242_vc1001              
;
RESPONSE:: The alert is generated due to disordered atoms of T-butyl groups. 
;
_vrf_PLAT911_vc1001              
;
RESPONSE::this is most probably related to low completeness. 
;
# end Validation Reply Form
_audit_creation_date             2023-03-21
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C25 H27 B F2 N2), 0.5[C7H8], 0.5[C4H10O]'
_chemical_formula_sum            'C50 H54 B2 F4 N4'
_chemical_formula_weight         808.59
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNBF
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   24.460(2)
_cell_length_b                   8.6052(8)
_cell_length_c                   24.688(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.579(11)
_cell_angle_gamma                90
_cell_volume                     5051.3(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2509
_cell_measurement_temperature    298
_cell_measurement_theta_max      21.4350
_cell_measurement_theta_min      3.1390
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.063
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1064
_diffrn_reflns_av_unetI/netI     0.1213
_diffrn_reflns_Laue_measured_fraction_full 0.831
_diffrn_reflns_Laue_measured_fraction_max 0.831
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21426
_diffrn_reflns_point_group_measured_fraction_full 0.831
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_theta_full        25.350
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.570
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.831
_diffrn_measured_fraction_theta_max 0.831
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  -9.00   0.50   47.21    --   10.80 -42.00 138.00   50
  2  ω     18.00  44.00   0.50   47.21    --   10.80  42.00 -68.00   52
  3  ω     13.00  38.00   0.50   47.21    --  -11.40  42.00 -68.00   50
  4  ω    -61.00 -36.00   0.50   47.21    --  -11.40 -42.00 138.00   50
  5  ω    -31.00  28.00   0.50   47.21    --   10.80  38.00  30.00  118
  6  ω     42.00  67.00   0.50   47.21    --   10.80  57.00-180.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0213571000
_diffrn_orient_matrix_UB_12      -0.0359706000
_diffrn_orient_matrix_UB_13      0.0206609000
_diffrn_orient_matrix_UB_21      -0.0205233000
_diffrn_orient_matrix_UB_22      -0.0251258000
_diffrn_orient_matrix_UB_23      0.0141185000
_diffrn_orient_matrix_UB_31      -0.0035602000
_diffrn_orient_matrix_UB_32      -0.0697874000
_diffrn_orient_matrix_UB_33      -0.0157285000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4031
_reflns_number_total             7689
_reflns_odcompleteness_completeness 75.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     553
_refine_ls_number_reflns         7689
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1369
_refine_ls_R_factor_gt           0.0756
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0990P)²+0.3611P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1941
_refine_ls_wR_factor_ref         0.2265
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00R(H00R), C00U(H00U), C00Z(H00Z), C010(H010), C011(H011), C013(H013),
 C016(H016), C017(H017), C018(H018), C019(H019), C01A(H01A), C01B(H01B)
2.b Idealised Me refined as rotating group:
 C01C(H01C,H01D,H01E), C01D(H01U,H01V,H01W), C01E(H01F,H01G,H01H), C01G(H01I,
 H01J,H01K), C01H(H01X,H01Y,H), C01I(H01L,H01M,H01N), C01J(H01Z,HA,HB),
 C01K(H01O,H01P,H01Q), C01L(H01,HC,HD), C01M(H0AA,HE,HF), C01N(H1AA,HG,HH),
 C01O(H01R,H01S,H01T)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.17503(9) 0.6945(3) 0.30523(9) 0.0843(7) Uani 1 1 d . . . . .
F002 F 0.16174(9) 0.8687(3) 0.36791(10) 0.0944(8) Uani 1 1 d . . . . .
F003 F 0.34498(9) 0.8469(3) 0.72636(11) 0.1003(8) Uani 1 1 d . . . . .
N004 N 0.24327(11) 0.8211(3) 0.68048(12) 0.0598(8) Uani 1 1 d . . . . .
F F 0.32219(12) 0.7160(3) 0.64576(12) 0.1185(10) Uani 1 1 d . . . . .
N006 N 0.28596(11) 0.9857(3) 0.64495(13) 0.0662(8) Uani 1 1 d . . . . .
N007 N 0.25870(11) 0.7694(3) 0.37860(12) 0.0617(8) Uani 1 1 d . . . . .
C008 C 0.15029(13) 1.0493(3) 0.58244(14) 0.0484(8) Uani 1 1 d . . . . .
N009 N 0.20500(11) 0.6146(3) 0.40439(12) 0.0620(8) Uani 1 1 d . . . . .
C00A C 0.10118(13) 1.1407(4) 0.56944(15) 0.0517(8) Uani 1 1 d . . . . .
C00B C 0.34410(13) 0.4855(4) 0.43349(14) 0.0523(9) Uani 1 1 d . . . . .
C00C C 0.16415(15) 0.9585(4) 0.53845(16) 0.0617(10) Uani 1 1 d . . . . .
H00C H 0.196309 0.896982 0.546386 0.074 Uiso 1 1 calc R . . . .
C00D C 0.16687(14) 1.1366(4) 0.67791(15) 0.0585(9) Uani 1 1 d . . . . .
H00D H 0.188421 1.133945 0.714346 0.070 Uiso 1 1 calc R . . . .
C00E C 0.39238(13) 0.4269(4) 0.47136(16) 0.0559(9) Uani 1 1 d . . . . .
C00F C 0.18298(13) 1.0492(4) 0.63713(14) 0.0513(8) Uani 1 1 d . . . . .
C00G C 0.30767(13) 0.5832(4) 0.45374(15) 0.0524(8) Uani 1 1 d . . . . .
C00H C 0.23530(13) 0.9546(4) 0.65325(14) 0.0531(9) Uani 1 1 d . . . . .
C00I C 0.08589(14) 1.2317(4) 0.61157(16) 0.0577(9) Uani 1 1 d . . . . .
C00J C 0.11954(15) 1.2266(4) 0.66498(16) 0.0635(10) Uani 1 1 d . . . . .
H00J H 0.109761 1.285772 0.692789 0.076 Uiso 1 1 calc R . . . .
C00K C 0.36592(16) 0.5627(4) 0.54648(17) 0.0707(11) Uani 1 1 d . . . . .
H00K H 0.372821 0.588331 0.584072 0.085 Uiso 1 1 calc R . . . .
C00L C 0.13221(16) 0.9604(4) 0.48683(16) 0.0702(10) Uani 1 1 d . . . . .
H00L H 0.142790 0.900861 0.459538 0.084 Uiso 1 1 calc R . . . .
C00M C 0.31901(14) 0.6208(4) 0.51012(16) 0.0628(10) Uani 1 1 d . . . . .
H00M H 0.294633 0.685726 0.523296 0.075 Uiso 1 1 calc R . . . .
C00N C 0.06705(13) 1.1416(4) 0.51384(15) 0.0545(9) Uani 1 1 d . . . . .
C00O C 0.40301(14) 0.4666(4) 0.52787(17) 0.0649(10) Uani 1 1 d . . . . .
C00P C 0.08255(15) 1.0505(4) 0.47232(16) 0.0641(10) Uani 1 1 d . . . . .
C00Q C 0.42997(14) 0.3280(4) 0.4510(2) 0.0688(11) Uani 1 1 d . . . . .
C00R C 0.33518(15) 0.4441(4) 0.37605(16) 0.0634(10) Uani 1 1 d . . . . .
H00R H 0.303675 0.482516 0.350841 0.076 Uiso 1 1 calc R . . . .
C00S C 0.25885(13) 0.6523(4) 0.41459(14) 0.0526(9) Uani 1 1 d . . . . .
C00T C 0.41961(16) 0.2916(4) 0.3939(2) 0.0774(12) Uani 1 1 d . . . . .
C00U C 0.37083(16) 0.3518(4) 0.35744(19) 0.0753(11) Uani 1 1 d . . . . .
H00U H 0.363345 0.326721 0.319770 0.090 Uiso 1 1 calc R . . . .
C00V C 0.17479(15) 0.4781(4) 0.41911(17) 0.0708(11) Uani 1 1 d . . . . .
C00W C 0.01785(15) 1.2344(4) 0.50078(18) 0.0695(11) Uani 1 1 d . . . . .
C00X C 0.20503(16) 0.6948(4) 0.68594(17) 0.0722(11) Uani 1 1 d . . . . .
C00Y C 0.29802(15) 0.8974(4) 0.37991(17) 0.0696(11) Uani 1 1 d . . . . .
C00Z C 0.03556(15) 1.3244(4) 0.5957(2) 0.0743(11) Uani 1 1 d . . . . .
H00Z H 0.024616 1.384973 0.622524 0.089 Uiso 1 1 calc R . . . .
C010 C 0.04805(18) 1.0533(5) 0.41834(18) 0.0836(12) Uani 1 1 d . . . . .
H010 H 0.057704 0.993491 0.390628 0.100 Uiso 1 1 calc R . . . .
C011 C 0.00440(16) 1.3254(5) 0.5437(2) 0.0791(12) Uani 1 1 d . . . . .
H011 H -0.027414 1.388207 0.535244 0.095 Uiso 1 1 calc R . . . .
C012 C 0.47879(16) 0.2682(5) 0.4901(3) 0.0862(14) Uani 1 1 d . . . . .
C013 C -0.01464(16) 1.2317(6) 0.4453(2) 0.0844(13) Uani 1 1 d . . . . .
H013 H -0.047020 1.292049 0.435669 0.101 Uiso 1 1 calc R . . . .
C014 C 0.31249(16) 1.1293(5) 0.6328(2) 0.0809(12) Uani 1 1 d . . . . .
B015 B 0.19342(17) 0.7472(5) 0.35896(18) 0.0623(11) Uani 1 1 d . . . . .
C016 C 0.0007(2) 1.1419(6) 0.4056(2) 0.0932(14) Uani 1 1 d . . . . .
H016 H -0.021523 1.141427 0.369452 0.112 Uiso 1 1 calc R . . . .
C017 C 0.4571(2) 0.1918(5) 0.3751(3) 0.1023(16) Uani 1 1 d . . . . .
H017 H 0.450709 0.163580 0.337780 0.123 Uiso 1 1 calc R . . . .
C018 C 0.45278(17) 0.4044(5) 0.5658(2) 0.0880(14) Uani 1 1 d . . . . .
H018 H 0.460272 0.429179 0.603509 0.106 Uiso 1 1 calc R . . . .
C019 C 0.48794(18) 0.3112(6) 0.5466(3) 0.0988(17) Uani 1 1 d . . . . .
H019 H 0.519683 0.273433 0.571623 0.119 Uiso 1 1 calc R . . . .
C01A C 0.5145(2) 0.1732(6) 0.4686(3) 0.114(2) Uani 1 1 d . . . . .
H01A H 0.546579 0.133609 0.492658 0.136 Uiso 1 1 calc R . . . .
C01B C 0.5041(2) 0.1366(6) 0.4139(4) 0.129(2) Uani 1 1 d . . . . .
H01B H 0.529229 0.072073 0.401694 0.155 Uiso 1 1 calc R . . . .
C01C C 0.11376(18) 0.5021(7) 0.3907(3) 0.133(2) Uani 1 1 d . . . . .
H01C H 0.099825 0.592594 0.405794 0.199 Uiso 1 1 calc GR . . . .
H01D H 0.092404 0.412827 0.396659 0.199 Uiso 1 1 calc GR . . . .
H01E H 0.110176 0.516287 0.351410 0.199 Uiso 1 1 calc GR . . . .
C01D C 0.2378(2) 0.5874(5) 0.7297(2) 0.1052(16) Uani 1 1 d . . . . .
H01U H 0.269436 0.546703 0.717522 0.158 Uiso 1 1 calc GR . . . .
H01V H 0.214027 0.503317 0.735549 0.158 Uiso 1 1 calc GR . . . .
H01W H 0.250769 0.643547 0.763869 0.158 Uiso 1 1 calc GR . . . .
C01E C 0.3039(2) 0.9925(5) 0.4321(2) 0.1139(17) Uani 1 1 d . . . . .
H01F H 0.267317 1.021601 0.436465 0.171 Uiso 1 1 calc GR . . . .
H01G H 0.325442 1.084283 0.429465 0.171 Uiso 1 1 calc GR . . . .
H01H H 0.322799 0.932189 0.463711 0.171 Uiso 1 1 calc GR . . . .
B01F B 0.3067(2) 0.8317(5) 0.6768(2) 0.0702(12) Uani 1 1 d . . . . .
C01G C 0.2728(2) 0.9961(6) 0.3288(2) 0.1186(18) Uani 1 1 d . . . . .
H01I H 0.268128 0.933477 0.295834 0.178 Uiso 1 1 calc GR . . . .
H01J H 0.297497 1.081345 0.326660 0.178 Uiso 1 1 calc GR . . . .
H01K H 0.236879 1.035426 0.331735 0.178 Uiso 1 1 calc GR . . . .
C01H C 0.1876(3) 0.6093(6) 0.6302(2) 0.133(2) Uani 1 1 d . . . . .
H01X H 0.165014 0.676788 0.602949 0.200 Uiso 1 1 calc GR . . . .
H01Y H 0.166289 0.518518 0.634668 0.200 Uiso 1 1 calc GR . . . .
H H 0.220607 0.579056 0.618143 0.200 Uiso 1 1 calc GR . . . .
C01I C 0.35510(19) 0.8413(6) 0.3761(3) 0.126(2) Uani 1 1 d . . . . .
H01L H 0.370734 0.776919 0.407704 0.189 Uiso 1 1 calc GR . . . .
H01M H 0.379300 0.928870 0.375654 0.189 Uiso 1 1 calc GR . . . .
H01N H 0.351785 0.782174 0.342504 0.189 Uiso 1 1 calc GR . . . .
C01J C 0.1539(2) 0.7532(6) 0.7041(3) 0.128(2) Uani 1 1 d . . . . .
H01Z H 0.165572 0.822058 0.735241 0.192 Uiso 1 1 calc GR . . . .
HA H 0.133979 0.666686 0.714722 0.192 Uiso 1 1 calc GR . . . .
HB H 0.129793 0.807850 0.673813 0.192 Uiso 1 1 calc GR . . . .
C01K C 0.1765(3) 0.4826(8) 0.4801(2) 0.152(3) Uani 1 1 d . . . . .
H01O H 0.214513 0.468521 0.501022 0.228 Uiso 1 1 calc GR . . . .
H01P H 0.153320 0.400986 0.488989 0.228 Uiso 1 1 calc GR . . . .
H01Q H 0.162712 0.581224 0.489286 0.228 Uiso 1 1 calc GR . . . .
C01L C 0.3216(2) 1.2334(6) 0.6850(3) 0.141(2) Uani 1 1 d . . . . .
H01 H 0.286164 1.275668 0.688206 0.212 Uiso 1 1 calc GR . . . .
HC H 0.346763 1.316622 0.681754 0.212 Uiso 1 1 calc GR . . . .
HD H 0.337490 1.172728 0.717503 0.212 Uiso 1 1 calc GR . . . .
C01M C 0.3685(2) 1.0829(7) 0.6225(3) 0.151(3) Uani 1 1 d . . . . .
H0AA H 0.388802 1.021984 0.653259 0.226 Uiso 1 1 calc GR . . . .
HE H 0.389728 1.174428 0.618719 0.226 Uiso 1 1 calc GR . . . .
HF H 0.362674 1.022646 0.588882 0.226 Uiso 1 1 calc GR . . . .
C01N C 0.2766(2) 1.2146(7) 0.5834(3) 0.150(3) Uani 1 1 d . . . . .
H1AA H 0.267695 1.146103 0.551819 0.224 Uiso 1 1 calc GR . . . .
HG H 0.296833 1.302983 0.574553 0.224 Uiso 1 1 calc GR . . . .
HH H 0.242411 1.248854 0.592375 0.224 Uiso 1 1 calc GR . . . .
C01O C 0.1975(3) 0.3326(6) 0.4017(4) 0.199(4) Uani 1 1 d . . . . .
H01R H 0.195206 0.335908 0.362374 0.299 Uiso 1 1 calc GR . . . .
H01S H 0.176044 0.246193 0.410009 0.299 Uiso 1 1 calc GR . . . .
H01T H 0.236091 0.321079 0.421433 0.299 Uiso 1 1 calc GR . . . .


_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
F001 B015 1.374(5) . ?
F002 B015 1.350(4) . ?
F003 B01F 1.362(5) . ?
N004 C00H 1.322(4) . ?
N004 C00X 1.461(4) . ?
N004 B01F 1.578(5) . ?
F B01F 1.363(5) . ?
N006 C00H 1.330(4) . ?
N006 C014 1.459(5) . ?
N006 B01F 1.563(5) . ?
N007 C00S 1.343(4) . ?
N007 C00Y 1.457(4) . ?
N007 B015 1.568(5) . ?
C008 C00A 1.408(4) . ?
C008 C00C 1.441(5) . ?
C008 C00F 1.398(5) . ?
N009 C00S 1.322(4) . ?
N009 C00V 1.478(4) . ?
N009 B015 1.578(5) . ?
C00A C00I 1.420(5) . ?
C00A C00N 1.429(5) . ?
C00B C00E 1.416(4) . ?
C00B C00G 1.400(5) . ?
C00B C00R 1.428(5) . ?
C00C H00C 0.9300 . ?
C00C C00L 1.329(5) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.386(5) . ?
C00D C00J 1.367(4) . ?
C00E C00O 1.400(5) . ?
C00E C00Q 1.428(5) . ?
C00F C00H 1.490(4) . ?
C00G C00M 1.392(5) . ?
C00G C00S 1.473(5) . ?
C00I C00J 1.382(5) . ?
C00I C00Z 1.442(5) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00K C00M 1.374(5) . ?
C00K C00O 1.384(5) . ?
C00L H00L 0.9300 . ?
C00L C00P 1.414(5) . ?
C00M H00M 0.9300 . ?
C00N C00P 1.411(5) . ?
C00N C00W 1.417(5) . ?
C00O C018 1.453(5) . ?
C00P C010 1.400(5) . ?
C00Q C00T 1.408(6) . ?
C00Q C012 1.443(6) . ?
C00R H00R 0.9300 . ?
C00R C00U 1.338(5) . ?
C00T C00U 1.413(6) . ?
C00T C017 1.412(6) . ?
C00U H00U 0.9300 . ?
C00V C01C 1.508(5) . ?
C00V C01K 1.496(7) . ?
C00V C01O 1.473(6) . ?
C00W C011 1.418(6) . ?
C00W C013 1.412(6) . ?
C00X C01D 1.502(5) . ?
C00X C01H 1.529(6) . ?
C00X C01J 1.509(6) . ?
C00Y C01E 1.505(6) . ?
C00Y C01G 1.526(6) . ?
C00Y C01I 1.501(6) . ?
C00Z H00Z 0.9300 . ?
C00Z C011 1.330(6) . ?
C010 H010 0.9300 . ?
C010 C016 1.360(6) . ?
C011 H011 0.9300 . ?
C012 C019 1.409(7) . ?
C012 C01A 1.389(7) . ?
C013 H013 0.9300 . ?
C013 C016 1.369(7) . ?
C014 C01L 1.542(7) . ?
C014 C01M 1.505(6) . ?
C014 C01N 1.516(6) . ?
C016 H016 0.9300 . ?
C017 H017 0.9300 . ?
C017 C01B 1.395(8) . ?
C018 H018 0.9300 . ?
C018 C019 1.341(7) . ?
C019 H019 0.9300 . ?
C01A H01A 0.9300 . ?
C01A C01B 1.351(8) . ?
C01B H01B 0.9300 . ?
C01C H01C 0.9600 . ?
C01C H01D 0.9600 . ?
C01C H01E 0.9600 . ?
C01D H01U 0.9600 . ?
C01D H01V 0.9600 . ?
C01D H01W 0.9600 . ?
C01E H01F 0.9600 . ?
C01E H01G 0.9600 . ?
C01E H01H 0.9600 . ?
C01G H01I 0.9600 . ?
C01G H01J 0.9600 . ?
C01G H01K 0.9600 . ?
C01H H01X 0.9600 . ?
C01H H01Y 0.9600 . ?
C01H H 0.9600 . ?
C01I H01L 0.9600 . ?
C01I H01M 0.9600 . ?
C01I H01N 0.9600 . ?
C01J H01Z 0.9600 . ?
C01J HA 0.9600 . ?
C01J HB 0.9600 . ?
C01K H01O 0.9600 . ?
C01K H01P 0.9600 . ?
C01K H01Q 0.9600 . ?
C01L H01 0.9600 . ?
C01L HC 0.9600 . ?
C01L HD 0.9600 . ?
C01M H0AA 0.9600 . ?
C01M HE 0.9600 . ?
C01M HF 0.9600 . ?
C01N H1AA 0.9600 . ?
C01N HG 0.9600 . ?
C01N HH 0.9600 . ?
C01O H01R 0.9600 . ?
C01O H01S 0.9600 . ?
C01O H01T 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00H N004 C00X 132.2(3) . . ?
C00H N004 B01F 87.1(3) . . ?
C00X N004 B01F 135.1(3) . . ?
C00H N006 C014 132.7(3) . . ?
C00H N006 B01F 87.5(3) . . ?
C014 N006 B01F 135.5(3) . . ?
C00S N007 C00Y 130.8(3) . . ?
C00S N007 B015 87.6(3) . . ?
C00Y N007 B015 135.9(3) . . ?
C00A C008 C00C 118.0(3) . . ?
C00F C008 C00A 119.0(3) . . ?
C00F C008 C00C 123.0(3) . . ?
C00S N009 C00V 132.9(3) . . ?
C00S N009 B015 87.9(3) . . ?
C00V N009 B015 137.1(3) . . ?
C008 C00A C00I 119.9(3) . . ?
C008 C00A C00N 119.8(3) . . ?
C00I C00A C00N 120.4(3) . . ?
C00E C00B C00R 118.5(3) . . ?
C00G C00B C00E 118.7(3) . . ?
C00G C00B C00R 122.8(3) . . ?
C008 C00C H00C 119.1 . . ?
C00L C00C C008 121.8(3) . . ?
C00L C00C H00C 119.1 . . ?
C00F C00D H00D 119.7 . . ?
C00J C00D H00D 119.7 . . ?
C00J C00D C00F 120.5(3) . . ?
C00B C00E C00Q 119.1(4) . . ?
C00O C00E C00B 120.2(3) . . ?
C00O C00E C00Q 120.8(3) . . ?
C008 C00F C00H 121.3(3) . . ?
C00D C00F C008 120.4(3) . . ?
C00D C00F C00H 118.4(3) . . ?
C00B C00G C00S 119.6(3) . . ?
C00M C00G C00B 120.1(3) . . ?
C00M C00G C00S 120.2(3) . . ?
N004 C00H N006 102.8(3) . . ?
N004 C00H C00F 128.7(3) . . ?
N006 C00H C00F 128.4(3) . . ?
C00A C00I C00Z 117.5(4) . . ?
C00J C00I C00A 118.8(3) . . ?
C00J C00I C00Z 123.8(4) . . ?
C00D C00J C00I 121.5(3) . . ?
C00D C00J H00J 119.2 . . ?
C00I C00J H00J 119.2 . . ?
C00M C00K H00K 119.6 . . ?
C00M C00K C00O 120.8(4) . . ?
C00O C00K H00K 119.6 . . ?
C00C C00L H00L 119.1 . . ?
C00C C00L C00P 121.7(3) . . ?
C00P C00L H00L 119.1 . . ?
C00G C00M H00M 119.7 . . ?
C00K C00M C00G 120.6(3) . . ?
C00K C00M H00M 119.7 . . ?
C00P C00N C00A 119.9(3) . . ?
C00P C00N C00W 120.4(3) . . ?
C00W C00N C00A 119.7(3) . . ?
C00E C00O C018 119.0(4) . . ?
C00K C00O C00E 119.6(3) . . ?
C00K C00O C018 121.4(4) . . ?
C00N C00P C00L 118.8(3) . . ?
C010 C00P C00L 122.7(4) . . ?
C010 C00P C00N 118.5(4) . . ?
C00E C00Q C012 118.5(5) . . ?
C00T C00Q C00E 120.4(3) . . ?
C00T C00Q C012 121.2(4) . . ?
C00B C00R H00R 119.0 . . ?
C00U C00R C00B 121.9(3) . . ?
C00U C00R H00R 119.0 . . ?
N007 C00S C00G 127.8(3) . . ?
N009 C00S N007 102.1(3) . . ?
N009 C00S C00G 130.1(3) . . ?
C00Q C00T C00U 118.8(4) . . ?
C00Q C00T C017 119.0(4) . . ?
C017 C00T C00U 122.1(5) . . ?
C00R C00U C00T 121.3(4) . . ?
C00R C00U H00U 119.3 . . ?
C00T C00U H00U 119.3 . . ?
N009 C00V C01C 105.9(3) . . ?
N009 C00V C01K 109.2(3) . . ?
C01K C00V C01C 104.8(4) . . ?
C01O C00V N009 111.0(4) . . ?
C01O C00V C01C 112.4(5) . . ?
C01O C00V C01K 113.1(5) . . ?
C00N C00W C011 118.4(4) . . ?
C013 C00W C00N 117.8(4) . . ?
C013 C00W C011 123.9(4) . . ?
N004 C00X C01D 106.2(3) . . ?
N004 C00X C01H 108.9(4) . . ?
N004 C00X C01J 111.9(3) . . ?
C01D C00X C01H 109.8(4) . . ?
C01D C00X C01J 109.3(4) . . ?
C01J C00X C01H 110.6(4) . . ?
N007 C00Y C01E 111.1(3) . . ?
N007 C00Y C01G 105.4(3) . . ?
N007 C00Y C01I 112.0(3) . . ?
C01E C00Y C01G 110.2(4) . . ?
C01I C00Y C01E 109.0(4) . . ?
C01I C00Y C01G 109.2(4) . . ?
C00I C00Z H00Z 119.2 . . ?
C011 C00Z C00I 121.7(4) . . ?
C011 C00Z H00Z 119.2 . . ?
C00P C010 H010 119.3 . . ?
C016 C010 C00P 121.3(5) . . ?
C016 C010 H010 119.3 . . ?
C00W C011 H011 118.8 . . ?
C00Z C011 C00W 122.5(4) . . ?
C00Z C011 H011 118.8 . . ?
C019 C012 C00Q 118.9(4) . . ?
C01A C012 C00Q 116.7(6) . . ?
C01A C012 C019 124.3(5) . . ?
C00W C013 H013 119.4 . . ?
C016 C013 C00W 121.1(4) . . ?
C016 C013 H013 119.4 . . ?
N006 C014 C01L 107.7(4) . . ?
N006 C014 C01M 106.1(4) . . ?
N006 C014 C01N 112.0(3) . . ?
C01M C014 C01L 109.7(4) . . ?
C01M C014 C01N 111.8(5) . . ?
C01N C014 C01L 109.5(5) . . ?
F001 B015 N007 114.7(3) . . ?
F001 B015 N009 114.3(3) . . ?
F002 B015 F001 110.1(3) . . ?
F002 B015 N007 115.9(3) . . ?
F002 B015 N009 117.2(3) . . ?
N007 B015 N009 82.4(2) . . ?
C010 C016 C013 120.9(4) . . ?
C010 C016 H016 119.6 . . ?
C013 C016 H016 119.6 . . ?
C00T C017 H017 120.8 . . ?
C01B C017 C00T 118.4(6) . . ?
C01B C017 H017 120.8 . . ?
C00O C018 H018 119.9 . . ?
C019 C018 C00O 120.1(5) . . ?
C019 C018 H018 119.9 . . ?
C012 C019 H019 118.6 . . ?
C018 C019 C012 122.7(4) . . ?
C018 C019 H019 118.6 . . ?
C012 C01A H01A 119.0 . . ?
C01B C01A C012 122.0(6) . . ?
C01B C01A H01A 119.0 . . ?
C017 C01B H01B 118.7 . . ?
C01A C01B C017 122.6(5) . . ?
C01A C01B H01B 118.7 . . ?
C00V C01C H01C 109.5 . . ?
C00V C01C H01D 109.5 . . ?
C00V C01C H01E 109.5 . . ?
H01C C01C H01D 109.5 . . ?
H01C C01C H01E 109.5 . . ?
H01D C01C H01E 109.5 . . ?
C00X C01D H01U 109.5 . . ?
C00X C01D H01V 109.5 . . ?
C00X C01D H01W 109.5 . . ?
H01U C01D H01V 109.5 . . ?
H01U C01D H01W 109.5 . . ?
H01V C01D H01W 109.5 . . ?
C00Y C01E H01F 109.5 . . ?
C00Y C01E H01G 109.5 . . ?
C00Y C01E H01H 109.5 . . ?
H01F C01E H01G 109.5 . . ?
H01F C01E H01H 109.5 . . ?
H01G C01E H01H 109.5 . . ?
F003 B01F N004 115.5(3) . . ?
F003 B01F F 110.6(4) . . ?
F003 B01F N006 116.4(4) . . ?
F B01F N004 113.4(4) . . ?
F B01F N006 115.9(4) . . ?
N006 B01F N004 82.6(3) . . ?
C00Y C01G H01I 109.5 . . ?
C00Y C01G H01J 109.5 . . ?
C00Y C01G H01K 109.5 . . ?
H01I C01G H01J 109.5 . . ?
H01I C01G H01K 109.5 . . ?
H01J C01G H01K 109.5 . . ?
C00X C01H H01X 109.5 . . ?
C00X C01H H01Y 109.5 . . ?
C00X C01H H 109.5 . . ?
H01X C01H H01Y 109.5 . . ?
H01X C01H H 109.5 . . ?
H01Y C01H H 109.5 . . ?
C00Y C01I H01L 109.5 . . ?
C00Y C01I H01M 109.5 . . ?
C00Y C01I H01N 109.5 . . ?
H01L C01I H01M 109.5 . . ?
H01L C01I H01N 109.5 . . ?
H01M C01I H01N 109.5 . . ?
C00X C01J H01Z 109.5 . . ?
C00X C01J HA 109.5 . . ?
C00X C01J HB 109.5 . . ?
H01Z C01J HA 109.5 . . ?
H01Z C01J HB 109.5 . . ?
HA C01J HB 109.5 . . ?
C00V C01K H01O 109.5 . . ?
C00V C01K H01P 109.5 . . ?
C00V C01K H01Q 109.5 . . ?
H01O C01K H01P 109.5 . . ?
H01O C01K H01Q 109.5 . . ?
H01P C01K H01Q 109.5 . . ?
C014 C01L H01 109.5 . . ?
C014 C01L HC 109.5 . . ?
C014 C01L HD 109.5 . . ?
H01 C01L HC 109.5 . . ?
H01 C01L HD 109.5 . . ?
HC C01L HD 109.5 . . ?
C014 C01M H0AA 109.5 . . ?
C014 C01M HE 109.5 . . ?
C014 C01M HF 109.5 . . ?
H0AA C01M HE 109.5 . . ?
H0AA C01M HF 109.5 . . ?
HE C01M HF 109.5 . . ?
C014 C01N H1AA 109.5 . . ?
C014 C01N HG 109.5 . . ?
C014 C01N HH 109.5 . . ?
H1AA C01N HG 109.5 . . ?
H1AA C01N HH 109.5 . . ?
HG C01N HH 109.5 . . ?
C00V C01O H01R 109.5 . . ?
C00V C01O H01S 109.5 . . ?
C00V C01O H01T 109.5 . . ?
H01R C01O H01S 109.5 . . ?
H01R C01O H01T 109.5 . . ?
H01S C01O H01T 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C008 C00A C00I C00J -0.8(5) . . . . ?
C008 C00A C00I C00Z 179.3(3) . . . . ?
C008 C00A C00N C00P 0.3(4) . . . . ?
C008 C00A C00N C00W -179.6(3) . . . . ?
C008 C00C C00L C00P -0.6(5) . . . . ?
C008 C00F C00H N004 -103.0(4) . . . . ?
C008 C00F C00H N006 78.8(4) . . . . ?
C00A C008 C00C C00L 0.4(5) . . . . ?
C00A C008 C00F C00D 0.6(5) . . . . ?
C00A C008 C00F C00H 179.9(3) . . . . ?
C00A C00I C00J C00D 0.1(5) . . . . ?
C00A C00I C00Z C011 0.0(5) . . . . ?
C00A C00N C00P C00L -0.4(5) . . . . ?
C00A C00N C00P C010 179.7(3) . . . . ?
C00A C00N C00W C011 0.6(5) . . . . ?
C00A C00N C00W C013 -180.0(3) . . . . ?
C00B C00E C00O C00K 0.3(5) . . . . ?
C00B C00E C00O C018 179.8(3) . . . . ?
C00B C00E C00Q C00T 1.1(5) . . . . ?
C00B C00E C00Q C012 -179.6(3) . . . . ?
C00B C00G C00M C00K 0.0(5) . . . . ?
C00B C00G C00S N007 -74.4(5) . . . . ?
C00B C00G C00S N009 103.6(4) . . . . ?
C00B C00R C00U C00T -0.6(6) . . . . ?
C00C C008 C00A C00I 179.9(3) . . . . ?
C00C C008 C00A C00N -0.2(4) . . . . ?
C00C C008 C00F C00D -178.7(3) . . . . ?
C00C C008 C00F C00H 0.6(5) . . . . ?
C00C C00L C00P C00N 0.6(5) . . . . ?
C00C C00L C00P C010 -179.5(4) . . . . ?
C00D C00F C00H N004 76.3(4) . . . . ?
C00D C00F C00H N006 -101.8(4) . . . . ?
C00E C00B C00G C00M -0.3(5) . . . . ?
C00E C00B C00G C00S 176.7(3) . . . . ?
C00E C00B C00R C00U 0.3(5) . . . . ?
C00E C00O C018 C019 0.4(6) . . . . ?
C00E C00Q C00T C00U -1.4(5) . . . . ?
C00E C00Q C00T C017 -179.2(3) . . . . ?
C00E C00Q C012 C019 -0.8(5) . . . . ?
C00E C00Q C012 C01A -179.6(4) . . . . ?
C00F C008 C00A C00I 0.5(4) . . . . ?
C00F C008 C00A C00N -179.6(3) . . . . ?
C00F C008 C00C C00L 179.8(3) . . . . ?
C00F C00D C00J C00I 1.1(5) . . . . ?
C00G C00B C00E C00O 0.1(5) . . . . ?
C00G C00B C00E C00Q -179.6(3) . . . . ?
C00G C00B C00R C00U 179.3(3) . . . . ?
C00H N004 C00X C01D -171.3(4) . . . . ?
C00H N004 C00X C01H 70.5(5) . . . . ?
C00H N004 C00X C01J -52.1(6) . . . . ?
C00H N004 B01F F003 115.2(4) . . . . ?
C00H N004 B01F F -115.6(4) . . . . ?
C00H N004 B01F N006 -0.5(3) . . . . ?
C00H N006 C014 C01L 68.1(5) . . . . ?
C00H N006 C014 C01M -174.5(4) . . . . ?
C00H N006 C014 C01N -52.3(6) . . . . ?
C00H N006 B01F F003 -114.4(4) . . . . ?
C00H N006 B01F N004 0.5(3) . . . . ?
C00H N006 B01F F 113.0(4) . . . . ?
C00I C00A C00N C00P -179.9(3) . . . . ?
C00I C00A C00N C00W 0.3(5) . . . . ?
C00I C00Z C011 C00W 1.0(6) . . . . ?
C00J C00D C00F C008 -1.4(5) . . . . ?
C00J C00D C00F C00H 179.2(3) . . . . ?
C00J C00I C00Z C011 -179.9(4) . . . . ?
C00K C00O C018 C019 179.9(4) . . . . ?
C00L C00P C010 C016 -179.6(4) . . . . ?
C00M C00G C00S N007 102.5(4) . . . . ?
C00M C00G C00S N009 -79.5(5) . . . . ?
C00M C00K C00O C00E -0.5(5) . . . . ?
C00M C00K C00O C018 180.0(3) . . . . ?
C00N C00A C00I C00J 179.3(3) . . . . ?
C00N C00A C00I C00Z -0.6(5) . . . . ?
C00N C00P C010 C016 0.3(5) . . . . ?
C00N C00W C011 C00Z -1.3(6) . . . . ?
C00N C00W C013 C016 0.3(6) . . . . ?
C00O C00E C00Q C00T -178.5(3) . . . . ?
C00O C00E C00Q C012 0.8(5) . . . . ?
C00O C00K C00M C00G 0.4(5) . . . . ?
C00O C018 C019 C012 -0.5(7) . . . . ?
C00P C00N C00W C011 -179.2(3) . . . . ?
C00P C00N C00W C013 0.2(5) . . . . ?
C00P C010 C016 C013 0.2(6) . . . . ?
C00Q C00E C00O C00K 180.0(3) . . . . ?
C00Q C00E C00O C018 -0.5(5) . . . . ?
C00Q C00T C00U C00R 1.2(6) . . . . ?
C00Q C00T C017 C01B -1.8(6) . . . . ?
C00Q C012 C019 C018 0.7(6) . . . . ?
C00Q C012 C01A C01B -0.6(7) . . . . ?
C00R C00B C00E C00O 179.1(3) . . . . ?
C00R C00B C00E C00Q -0.6(5) . . . . ?
C00R C00B C00G C00M -179.2(3) . . . . ?
C00R C00B C00G C00S -2.2(5) . . . . ?
C00S N007 C00Y C01E -57.6(5) . . . . ?
C00S N007 C00Y C01G -176.9(4) . . . . ?
C00S N007 C00Y C01I 64.5(5) . . . . ?
C00S N007 B015 F001 -113.3(4) . . . . ?
C00S N007 B015 F002 116.7(3) . . . . ?
C00S N007 B015 N009 0.1(2) . . . . ?
C00S N009 C00V C01C -175.6(4) . . . . ?
C00S N009 C00V C01K 72.0(6) . . . . ?
C00S N009 C00V C01O -53.3(7) . . . . ?
C00S N009 B015 F001 113.7(3) . . . . ?
C00S N009 B015 F002 -115.4(4) . . . . ?
C00S N009 B015 N007 -0.1(3) . . . . ?
C00S C00G C00M C00K -176.9(3) . . . . ?
C00T C00Q C012 C019 178.5(4) . . . . ?
C00T C00Q C012 C01A -0.3(6) . . . . ?
C00T C017 C01B C01A 0.9(8) . . . . ?
C00U C00T C017 C01B -179.5(4) . . . . ?
C00V N009 C00S N007 165.3(4) . . . . ?
C00V N009 C00S C00G -13.1(6) . . . . ?
C00V N009 B015 F001 -50.4(6) . . . . ?
C00V N009 B015 F002 80.6(6) . . . . ?
C00V N009 B015 N007 -164.1(4) . . . . ?
C00W C00N C00P C00L 179.4(3) . . . . ?
C00W C00N C00P C010 -0.5(5) . . . . ?
C00W C013 C016 C010 -0.5(7) . . . . ?
C00X N004 C00H N006 -155.1(4) . . . . ?
C00X N004 C00H C00F 26.3(6) . . . . ?
C00X N004 B01F F003 -90.3(5) . . . . ?
C00X N004 B01F F 38.9(6) . . . . ?
C00X N004 B01F N006 154.0(4) . . . . ?
C00Y N007 C00S N009 155.7(3) . . . . ?
C00Y N007 C00S C00G -25.9(6) . . . . ?
C00Y N007 B015 F001 93.2(5) . . . . ?
C00Y N007 B015 F002 -36.8(6) . . . . ?
C00Y N007 B015 N009 -153.4(4) . . . . ?
C00Z C00I C00J C00D 179.9(3) . . . . ?
C011 C00W C013 C016 179.7(4) . . . . ?
C012 C00Q C00T C00U 179.3(3) . . . . ?
C012 C00Q C00T C017 1.6(6) . . . . ?
C012 C01A C01B C017 0.3(9) . . . . ?
C013 C00W C011 C00Z 179.4(4) . . . . ?
C014 N006 C00H N004 -159.2(4) . . . . ?
C014 N006 C00H C00F 19.4(6) . . . . ?
C014 N006 B01F F003 43.1(6) . . . . ?
C014 N006 B01F N004 158.0(4) . . . . ?
C014 N006 B01F F -89.6(6) . . . . ?
B015 N007 C00S N009 -0.1(3) . . . . ?
B015 N007 C00S C00G 178.4(4) . . . . ?
B015 N007 C00Y C01E 86.3(5) . . . . ?
B015 N007 C00Y C01G -33.0(6) . . . . ?
B015 N007 C00Y C01I -151.6(4) . . . . ?
B015 N009 C00S N007 0.1(3) . . . . ?
B015 N009 C00S C00G -178.3(4) . . . . ?
B015 N009 C00V C01C -17.6(6) . . . . ?
B015 N009 C00V C01K -130.0(5) . . . . ?
B015 N009 C00V C01O 104.7(6) . . . . ?
C017 C00T C00U C00R 178.9(4) . . . . ?
C019 C012 C01A C01B -179.4(5) . . . . ?
C01A C012 C019 C018 179.4(4) . . . . ?
B01F N004 C00H N006 0.6(3) . . . . ?
B01F N004 C00H C00F -177.9(4) . . . . ?
B01F N004 C00X C01D 44.2(6) . . . . ?
B01F N004 C00X C01H -74.1(5) . . . . ?
B01F N004 C00X C01J 163.4(4) . . . . ?
B01F N006 C00H N004 -0.6(3) . . . . ?
B01F N006 C00H C00F 177.9(4) . . . . ?
B01F N006 C014 C01L -80.5(5) . . . . ?
B01F N006 C014 C01M 36.9(6) . . . . ?
B01F N006 C014 C01N 159.1(5) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.183 0.250 226.9 56.7 0.5C7H8
2 0.000 -0.815 0.750 226.9 56.7 0.5C7H8
3 0.500 -0.337 0.250 252.6 43.7 0.5C4H10O
4 0.500 -0.296 0.750 252.6 43.7 0.5C4H10O

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.364
_oxdiff_exptl_absorpt_empirical_full_min 0.813
####################################################################### 
# 
# 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_4Li
_audit_block_doi                 10.5517/ccdc.csd.cc2f74b5
_database_code_depnum_ccdc_archive 'CCDC 2241186'
loop_
_audit_author_name
_audit_author_address
'Ramkumar Kannan'
;Tata Institute of Fundamental Research Hyderabad
India
;
_audit_update_record             
;
2023-05-08 deposited with the CCDC.	2023-10-20 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         'C31 H43 Li N2 O2'
_chemical_formula_sum            'C31 H43 Li N2 O2'
_chemical_formula_weight         482.61

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'
Li Li -0.0003 0.0001 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   15.8107(8)
_cell_length_b                   18.7330(8)
_cell_length_c                   19.3851(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5741.5(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    108(2)
_cell_measurement_reflns_used    9962
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      31.38

_exptl_crystal_description       sphere
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_F_000             2096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.307
_exptl_crystal_size_min          0.299
_exptl_absorpt_coefficient_mu    0.068
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      108(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36173
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.415
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5029
_reflns_number_gt                4454
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0454P)²+2.4467P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5029
_refine_ls_number_parameters     448
_refine_ls_number_restraints     583
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1069
_refine_ls_wR_factor_gt          0.1023
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6577(5) 0.6265(4) 0.6474(6) 0.031(2) Uani 0.54(2) 1 d D U P A 1
O1A O 0.6593(6) 0.6282(5) 0.6486(6) 0.025(3) Uani 0.46(2) 1 d D U P A 2
O2 O 0.7837(2) 0.5022(2) 0.6241(2) 0.0394(8) Uani 0.606(5) 1 d D U P A 1
O2A O 0.7538(4) 0.4919(3) 0.6146(3) 0.0326(11) Uani 0.394(5) 1 d D U P A 2
N1 N 0.82105(6) 0.64840(6) 0.53052(5) 0.0240(2) Uani 1 1 d . . . . .
N2 N 0.71288(7) 0.59091(7) 0.48182(6) 0.0324(3) Uani 1 1 d . . . . .
C1 C 0.77682(8) 0.63612(6) 0.47343(6) 0.0221(3) Uani 1 1 d . . . . .
C2 C 0.79969(8) 0.66885(7) 0.40474(6) 0.0223(3) Uani 1 1 d . . . . .
C3 C 0.76659(8) 0.73549(7) 0.38545(6) 0.0261(3) Uani 1 1 d . . . . .
C4 C 0.70890(9) 0.77420(8) 0.42840(7) 0.0324(3) Uani 1 1 d . . . . .
H4 H 0.692107 0.754403 0.471387 0.039 Uiso 1 1 calc R U . . .
C5 C 0.67778(10) 0.83857(8) 0.40891(8) 0.0397(4) Uani 1 1 d . . . . .
H5 H 0.639311 0.863096 0.438161 0.048 Uiso 1 1 calc R U . . .
C6 C 0.70229(10) 0.86966(8) 0.34500(9) 0.0432(4) Uani 1 1 d . . . . .
H6 H 0.680536 0.915000 0.332077 0.052 Uiso 1 1 calc R U . . .
C7 C 0.75647(10) 0.83498(8) 0.30247(8) 0.0388(4) Uani 1 1 d . . . . .
H7 H 0.772239 0.856373 0.259942 0.047 Uiso 1 1 calc R U . . .
C8 C 0.79035(9) 0.76662(7) 0.32058(7) 0.0294(3) Uani 1 1 d . . . . .
C9 C 0.84547(9) 0.72983(7) 0.27729(7) 0.0300(3) Uani 1 1 d . . . . .
H9 H 0.860884 0.750418 0.234307 0.036 Uiso 1 1 calc R U . . .
C10 C 0.87850(8) 0.66362(7) 0.29550(6) 0.0253(3) Uani 1 1 d . . . . .
C11 C 0.93615(9) 0.62611(8) 0.25175(7) 0.0321(3) Uani 1 1 d . . . . .
H11 H 0.951796 0.646308 0.208647 0.039 Uiso 1 1 calc R U . . .
C12 C 0.96882(9) 0.56222(8) 0.27079(7) 0.0339(3) Uani 1 1 d . . . . .
H12 H 1.007254 0.538201 0.241121 0.041 Uiso 1 1 calc R U . . .
C13 C 0.94595(8) 0.53100(7) 0.33479(7) 0.0307(3) Uani 1 1 d . . . . .
H13 H 0.968992 0.486071 0.347589 0.037 Uiso 1 1 calc R U . . .
C14 C 0.89121(8) 0.56491(7) 0.37805(7) 0.0256(3) Uani 1 1 d . . . . .
H14 H 0.876566 0.543266 0.420730 0.031 Uiso 1 1 calc R U . . .
C15 C 0.85555(7) 0.63236(7) 0.36032(6) 0.0220(3) Uani 1 1 d . . . . .
C16 C 0.89351(8) 0.69605(7) 0.54153(6) 0.0253(3) Uani 1 1 d . . . . .
C17 C 0.96124(9) 0.69970(9) 0.48503(7) 0.0396(4) Uani 1 1 d . . . . .
H17A H 0.978715 0.651230 0.472444 0.059 Uiso 1 1 calc R U . . .
H17B H 1.010269 0.726359 0.502141 0.059 Uiso 1 1 calc R U . . .
H17C H 0.938012 0.723856 0.444380 0.059 Uiso 1 1 calc R U . . .
C18 C 0.93634(9) 0.66674(8) 0.60643(7) 0.0363(3) Uani 1 1 d . . . . .
H18A H 0.894593 0.662850 0.643613 0.054 Uiso 1 1 calc R U . . .
H18B H 0.981796 0.699122 0.620634 0.054 Uiso 1 1 calc R U . . .
H18C H 0.960036 0.619484 0.596601 0.054 Uiso 1 1 calc R U . . .
C19 C 0.86353(9) 0.77219(8) 0.55743(8) 0.0379(3) Uani 1 1 d . . . . .
H19A H 0.838759 0.793307 0.515823 0.057 Uiso 1 1 calc R U . . .
H19B H 0.911763 0.801111 0.572506 0.057 Uiso 1 1 calc R U . . .
H19C H 0.820918 0.770797 0.594119 0.057 Uiso 1 1 calc R U . . .
C20 C 0.64817(9) 0.56782(8) 0.43232(7) 0.0352(3) Uani 1 1 d D U . . .
C21 C 0.67428(16) 0.55606(17) 0.35794(12) 0.0427(6) Uani 0.780(3) 1 d D U P B 1
H21A H 0.683540 0.602317 0.335557 0.064 Uiso 0.780(3) 1 calc R U P B 1
H21B H 0.629501 0.530110 0.333596 0.064 Uiso 0.780(3) 1 calc R U P B 1
H21C H 0.726691 0.528165 0.356578 0.064 Uiso 0.780(3) 1 calc R U P B 1
C21A C 0.6105(5) 0.6403(4) 0.3795(4) 0.045(2) Uani 0.220(3) 1 d D U P B 2
H21D H 0.595852 0.680964 0.408871 0.067 Uiso 0.220(3) 1 calc R U P B 2
H21E H 0.560354 0.624799 0.353814 0.067 Uiso 0.220(3) 1 calc R U P B 2
H21F H 0.654917 0.654421 0.346930 0.067 Uiso 0.220(3) 1 calc R U P B 2
C22 C 0.62204(13) 0.49086(10) 0.45952(11) 0.0425(6) Uani 0.780(3) 1 d D U P B 1
H22A H 0.669901 0.458062 0.454270 0.064 Uiso 0.780(3) 1 calc R U P B 1
H22B H 0.573834 0.473152 0.432744 0.064 Uiso 0.780(3) 1 calc R U P B 1
H22C H 0.606275 0.493911 0.508327 0.064 Uiso 0.780(3) 1 calc R U P B 1
C22A C 0.6802(6) 0.5216(5) 0.3798(5) 0.044(2) Uani 0.220(3) 1 d D U P B 2
H22D H 0.723856 0.546675 0.353305 0.066 Uiso 0.220(3) 1 calc R U P B 2
H22E H 0.634032 0.507552 0.348977 0.066 Uiso 0.220(3) 1 calc R U P B 2
H22F H 0.704755 0.478971 0.401180 0.066 Uiso 0.220(3) 1 calc R U P B 2
C23 C 0.57276(12) 0.61458(11) 0.43819(12) 0.0422(6) Uani 0.780(3) 1 d D U P B 1
H23A H 0.556106 0.618460 0.486740 0.063 Uiso 0.780(3) 1 calc R U P B 1
H23B H 0.526061 0.594051 0.411518 0.063 Uiso 0.780(3) 1 calc R U P B 1
H23C H 0.586314 0.662107 0.420187 0.063 Uiso 0.780(3) 1 calc R U P B 1
C23A C 0.5705(5) 0.5524(5) 0.4670(4) 0.057(3) Uani 0.220(3) 1 d D U P B 2
H23D H 0.579838 0.514477 0.500945 0.086 Uiso 0.220(3) 1 calc R U P B 2
H23E H 0.528200 0.536832 0.433308 0.086 Uiso 0.220(3) 1 calc R U P B 2
H23F H 0.550336 0.595486 0.490550 0.086 Uiso 0.220(3) 1 calc R U P B 2
C24 C 0.64035(10) 0.70250(8) 0.64458(9) 0.0375(3) Uani 1 1 d D U . . .
H24A H 0.631827 0.717828 0.596201 0.045 Uiso 0.54(2) 1 calc R U P A 1
H24B H 0.688424 0.729672 0.664093 0.045 Uiso 0.54(2) 1 calc R U P A 1
C25 C 0.5622(7) 0.7158(6) 0.6857(7) 0.043(2) Uani 0.54(2) 1 d D U P A 1
H25A H 0.528549 0.755494 0.666120 0.051 Uiso 0.54(2) 1 calc R U P A 1
H25B H 0.575785 0.726630 0.734493 0.051 Uiso 0.54(2) 1 calc R U P A 1
C25A C 0.5668(8) 0.7119(7) 0.6942(9) 0.044(3) Uani 0.46(2) 1 d D U P A 2
H25C H 0.534065 0.755623 0.683959 0.053 Uiso 0.46(2) 1 calc R U P A 2
H25D H 0.586194 0.713173 0.742779 0.053 Uiso 0.46(2) 1 calc R U P A 2
C26 C 0.51592(12) 0.64468(10) 0.67897(13) 0.0613(5) Uani 1 1 d D U . . .
H26A H 0.483974 0.634072 0.721674 0.074 Uiso 0.54(2) 1 calc R U P A 1
H26B H 0.475703 0.646258 0.639854 0.074 Uiso 0.54(2) 1 calc R U P A 1
C27 C 0.5813(6) 0.5894(4) 0.6669(7) 0.040(2) Uani 0.54(2) 1 d D U P A 1
H27A H 0.590805 0.561157 0.709343 0.048 Uiso 0.54(2) 1 calc R U P A 1
H27B H 0.563259 0.556617 0.629620 0.048 Uiso 0.54(2) 1 calc R U P A 1
C27A C 0.5871(6) 0.5911(4) 0.6755(7) 0.0299(19) Uani 0.46(2) 1 d D U P A 2
H27C H 0.599595 0.572043 0.722047 0.036 Uiso 0.46(2) 1 calc R U P A 2
H27D H 0.571673 0.550882 0.644953 0.036 Uiso 0.46(2) 1 calc R U P A 2
C28 C 0.8374(2) 0.46204(14) 0.57781(14) 0.0350(8) Uani 0.606(5) 1 d D U P A 1
H28A H 0.895541 0.481667 0.578012 0.042 Uiso 0.606(5) 1 calc R U P A 1
H28B H 0.815116 0.464078 0.530123 0.042 Uiso 0.606(5) 1 calc R U P A 1
C28A C 0.7850(4) 0.4427(2) 0.5633(2) 0.0419(13) Uani 0.394(5) 1 d D U P A 2
H28C H 0.814922 0.468583 0.526043 0.050 Uiso 0.394(5) 1 calc R U P A 2
H28D H 0.737910 0.415116 0.542733 0.050 Uiso 0.394(5) 1 calc R U P A 2
C29 C 0.8373(7) 0.3860(4) 0.6040(4) 0.0396(18) Uani 0.606(5) 1 d D U P A 1
H29A H 0.802165 0.355159 0.574059 0.048 Uiso 0.606(5) 1 calc R U P A 1
H29B H 0.895487 0.366623 0.605406 0.048 Uiso 0.606(5) 1 calc R U P A 1
C29A C 0.8452(9) 0.3936(6) 0.6012(6) 0.034(2) Uani 0.394(5) 1 d D U P A 2
H29C H 0.903637 0.412508 0.600260 0.041 Uiso 0.394(5) 1 calc R U P A 2
H29D H 0.844697 0.345088 0.581036 0.041 Uiso 0.394(5) 1 calc R U P A 2
C30 C 0.8005(7) 0.3902(4) 0.6754(4) 0.0367(19) Uani 0.606(5) 1 d D U P A 1
H30A H 0.841402 0.373258 0.710402 0.044 Uiso 0.606(5) 1 calc R U P A 1
H30B H 0.747872 0.361881 0.678979 0.044 Uiso 0.606(5) 1 calc R U P A 1
C30A C 0.8097(10) 0.3934(6) 0.6743(6) 0.034(2) Uani 0.394(5) 1 d D U P A 2
H30C H 0.782204 0.347305 0.685191 0.041 Uiso 0.394(5) 1 calc R U P A 2
H30D H 0.854500 0.403037 0.708695 0.041 Uiso 0.394(5) 1 calc R U P A 2
C31 C 0.7827(3) 0.46992(17) 0.68363(16) 0.0349(8) Uani 0.606(5) 1 d D U P A 1
H31A H 0.726774 0.476587 0.705602 0.042 Uiso 0.606(5) 1 calc R U P A 1
H31B H 0.826028 0.491415 0.714135 0.042 Uiso 0.606(5) 1 calc R U P A 1
C31A C 0.7456(4) 0.4537(3) 0.6719(3) 0.0425(13) Uani 0.394(5) 1 d D U P A 2
H31C H 0.687815 0.433551 0.674156 0.051 Uiso 0.394(5) 1 calc R U P A 2
H31D H 0.753682 0.485041 0.712454 0.051 Uiso 0.394(5) 1 calc R U P A 2
Li1 Li 0.73805(14) 0.58824(11) 0.58222(11) 0.0288(5) Uani 1 1 d D . . . .
H24C H 0.625(2) 0.7114(18) 0.5960(18) 0.035 Uiso 0.46(2) 1 d . U P A 2
H24D H 0.695(2) 0.7275(18) 0.6567(17) 0.035 Uiso 0.46(2) 1 d . U P A 2
H26C H 0.467(2) 0.6355(18) 0.7017(18) 0.035 Uiso 0.46(2) 1 d . U P A 2
H26D H 0.496(2) 0.6590(18) 0.6183(18) 0.035 Uiso 0.46(2) 1 d . U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C27 1.444(8) . ?
O1 C24 1.450(7) . ?
O1 Li1 1.930(7) . ?
O1A C24 1.425(9) . ?
O1A C27A 1.433(9) . ?
O1A Li1 1.942(7) . ?
O2 C31 1.303(4) . ?
O2 C28 1.446(4) . ?
O2 Li1 1.943(4) . ?
O2A C31A 1.328(7) . ?
O2A C28A 1.444(6) . ?
O2A Li1 1.927(6) . ?
N1 C1 1.3292(16) . ?
N1 C16 1.4679(16) . ?
N1 Li1 1.999(2) . ?
N2 C1 1.3287(17) . ?
N2 C20 1.4678(17) . ?
N2 Li1 1.987(2) . ?
C1 C2 1.5099(17) . ?
C1 Li1 2.372(2) . ?
C2 C3 1.4042(18) . ?
C2 C15 1.4102(17) . ?
C3 C4 1.4322(19) . ?
C3 C8 1.4362(18) . ?
C4 C5 1.356(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.423(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.355(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.4318(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(2) . ?
C9 C10 1.3913(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.4295(19) . ?
C10 C15 1.4331(17) . ?
C11 C12 1.355(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.418(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3624(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.4256(18) . ?
C14 H14 0.9500 . ?
C16 C18 1.5305(18) . ?
C16 C17 1.5333(18) . ?
C16 C19 1.5345(19) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C23A 1.429(7) . ?
C20 C22A 1.429(8) . ?
C20 C23 1.484(2) . ?
C20 C21 1.516(3) . ?
C20 C22 1.590(2) . ?
C20 C21A 1.802(7) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21A H21D 0.9800 . ?
C21A H21E 0.9800 . ?
C21A H21F 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C22A H22D 0.9800 . ?
C22A H22E 0.9800 . ?
C22A H22F 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C23A H23D 0.9800 . ?
C23A H23E 0.9800 . ?
C23A H23F 0.9800 . ?
C24 C25 1.492(9) . ?
C24 C25A 1.519(10) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 H24C 0.99(3) . ?
C24 H24D 1.01(3) . ?
C25 C26 1.526(9) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25A C26 1.523(11) . ?
C25A H25C 0.9900 . ?
C25A H25D 0.9900 . ?
C26 C27 1.482(8) . ?
C26 C27A 1.509(9) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 H26C 0.91(4) . ?
C26 H26D 1.25(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27A H27C 0.9900 . ?
C27A H27D 0.9900 . ?
C28 C29 1.512(7) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28A C29A 1.512(11) . ?
C28A H28C 0.9900 . ?
C28A H28D 0.9900 . ?
C29 C30 1.502(7) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29A C30A 1.524(11) . ?
C29A H29C 0.9900 . ?
C29A H29D 0.9900 . ?
C30 C31 1.527(7) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30A C31A 1.517(10) . ?
C30A H30C 0.9900 . ?
C30A H30D 0.9900 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31A H31C 0.9900 . ?
C31A H31D 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C27 O1 C24 108.9(5) . . ?
C27 O1 Li1 122.9(7) . . ?
C24 O1 Li1 117.7(5) . . ?
C24 O1A C27A 109.0(6) . . ?
C24 O1A Li1 118.3(5) . . ?
C27A O1A Li1 124.4(7) . . ?
C31 O2 C28 108.4(3) . . ?
C31 O2 Li1 138.6(3) . . ?
C28 O2 Li1 113.0(2) . . ?
C31A O2A C28A 105.3(4) . . ?
C31A O2A Li1 139.9(5) . . ?
C28A O2A Li1 114.7(4) . . ?
C1 N1 C16 129.57(10) . . ?
C1 N1 Li1 88.54(10) . . ?
C16 N1 Li1 141.46(10) . . ?
C1 N2 C20 129.66(12) . . ?
C1 N2 Li1 89.06(10) . . ?
C20 N2 Li1 140.57(11) . . ?
N2 C1 N1 114.13(11) . . ?
N2 C1 C2 123.29(11) . . ?
N1 C1 C2 122.55(11) . . ?
N2 C1 Li1 56.88(9) . . ?
N1 C1 Li1 57.40(8) . . ?
C2 C1 Li1 178.02(10) . . ?
C3 C2 C15 120.12(11) . . ?
C3 C2 C1 120.44(11) . . ?
C15 C2 C1 119.44(11) . . ?
C2 C3 C4 122.19(12) . . ?
C2 C3 C8 119.78(12) . . ?
C4 C3 C8 118.03(12) . . ?
C5 C4 C3 121.30(14) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 120.52(14) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 120.39(14) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 121.08(14) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 121.95(13) . . ?
C9 C8 C3 119.37(12) . . ?
C7 C8 C3 118.68(13) . . ?
C10 C9 C8 121.56(12) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 121.80(12) . . ?
C9 C10 C15 119.45(12) . . ?
C11 C10 C15 118.74(12) . . ?
C12 C11 C10 121.04(13) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 120.36(12) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 120.53(13) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 121.08(12) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C2 C15 C14 122.02(11) . . ?
C2 C15 C10 119.73(11) . . ?
C14 C15 C10 118.25(11) . . ?
N1 C16 C18 104.28(10) . . ?
N1 C16 C17 117.92(10) . . ?
C18 C16 C17 107.12(11) . . ?
N1 C16 C19 110.69(10) . . ?
C18 C16 C19 107.76(11) . . ?
C17 C16 C19 108.53(12) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 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 . . ?
C23A C20 C22A 121.2(5) . . ?
C23A C20 N2 110.5(3) . . ?
C22A C20 N2 113.4(4) . . ?
N2 C20 C23 109.63(13) . . ?
N2 C20 C21 118.34(14) . . ?
C23 C20 C21 112.18(18) . . ?
N2 C20 C22 103.40(13) . . ?
C23 C20 C22 107.52(14) . . ?
C21 C20 C22 104.74(17) . . ?
C23A C20 C21A 97.8(5) . . ?
C22A C20 C21A 99.7(5) . . ?
N2 C20 C21A 112.3(2) . . ?
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 C21A H21D 109.5 . . ?
C20 C21A H21E 109.5 . . ?
H21D C21A H21E 109.5 . . ?
C20 C21A H21F 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 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 . . ?
C20 C22A H22D 109.5 . . ?
C20 C22A H22E 109.5 . . ?
H22D C22A H22E 109.5 . . ?
C20 C22A H22F 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C23A H23D 109.5 . . ?
C20 C23A H23E 109.5 . . ?
H23D C23A H23E 109.5 . . ?
C20 C23A H23F 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
O1 C24 C25 107.5(5) . . ?
O1A C24 C25A 103.8(6) . . ?
O1 C24 H24A 110.2 . . ?
C25 C24 H24A 110.2 . . ?
O1 C24 H24B 110.2 . . ?
C25 C24 H24B 110.2 . . ?
H24A C24 H24B 108.5 . . ?
O1A C24 H24C 106(2) . . ?
C25A C24 H24C 114(2) . . ?
O1A C24 H24D 105(2) . . ?
C25A C24 H24D 117(2) . . ?
H24C C24 H24D 111(3) . . ?
C24 C25 C26 101.8(6) . . ?
C24 C25 H25A 111.4 . . ?
C26 C25 H25A 111.4 . . ?
C24 C25 H25B 111.4 . . ?
C26 C25 H25B 111.4 . . ?
H25A C25 H25B 109.3 . . ?
C24 C25A C26 100.7(6) . . ?
C24 C25A H25C 111.6 . . ?
C26 C25A H25C 111.6 . . ?
C24 C25A H25D 111.6 . . ?
C26 C25A H25D 111.6 . . ?
H25C C25A H25D 109.4 . . ?
C27A C26 C25A 99.4(7) . . ?
C27 C26 C25 106.8(6) . . ?
C27 C26 H26A 110.4 . . ?
C25 C26 H26A 110.4 . . ?
C27 C26 H26B 110.4 . . ?
C25 C26 H26B 110.4 . . ?
H26A C26 H26B 108.6 . . ?
C27A C26 H26C 122(2) . . ?
C25A C26 H26C 121(2) . . ?
C27A C26 H26D 106.6(16) . . ?
C25A C26 H26D 97.9(17) . . ?
H26C C26 H26D 107(3) . . ?
O1 C27 C26 106.8(6) . . ?
O1 C27 H27A 110.4 . . ?
C26 C27 H27A 110.4 . . ?
O1 C27 H27B 110.4 . . ?
C26 C27 H27B 110.4 . . ?
H27A C27 H27B 108.6 . . ?
O1A C27A C26 106.7(6) . . ?
O1A C27A H27C 110.4 . . ?
C26 C27A H27C 110.4 . . ?
O1A C27A H27D 110.4 . . ?
C26 C27A H27D 110.4 . . ?
H27C C27A H27D 108.6 . . ?
O2 C28 C29 106.3(3) . . ?
O2 C28 H28A 110.5 . . ?
C29 C28 H28A 110.5 . . ?
O2 C28 H28B 110.5 . . ?
C29 C28 H28B 110.5 . . ?
H28A C28 H28B 108.7 . . ?
O2A C28A C29A 105.6(5) . . ?
O2A C28A H28C 110.6 . . ?
C29A C28A H28C 110.6 . . ?
O2A C28A H28D 110.6 . . ?
C29A C28A H28D 110.6 . . ?
H28C C28A H28D 108.8 . . ?
C30 C29 C28 105.1(4) . . ?
C30 C29 H29A 110.7 . . ?
C28 C29 H29A 110.7 . . ?
C30 C29 H29B 110.7 . . ?
C28 C29 H29B 110.7 . . ?
H29A C29 H29B 108.8 . . ?
C28A C29A C30A 102.8(7) . . ?
C28A C29A H29C 111.2 . . ?
C30A C29A H29C 111.2 . . ?
C28A C29A H29D 111.2 . . ?
C30A C29A H29D 111.2 . . ?
H29C C29A H29D 109.1 . . ?
C29 C30 C31 102.6(4) . . ?
C29 C30 H30A 111.2 . . ?
C31 C30 H30A 111.2 . . ?
C29 C30 H30B 111.2 . . ?
C31 C30 H30B 111.2 . . ?
H30A C30 H30B 109.2 . . ?
C31A C30A C29A 102.4(6) . . ?
C31A C30A H30C 111.3 . . ?
C29A C30A H30C 111.3 . . ?
C31A C30A H30D 111.3 . . ?
C29A C30A H30D 111.3 . . ?
H30C C30A H30D 109.2 . . ?
O2 C31 C30 111.0(3) . . ?
O2 C31 H31A 109.4 . . ?
C30 C31 H31A 109.4 . . ?
O2 C31 H31B 109.4 . . ?
C30 C31 H31B 109.4 . . ?
H31A C31 H31B 108.0 . . ?
O2A C31A C30A 111.2(5) . . ?
O2A C31A H31C 109.4 . . ?
C30A C31A H31C 109.4 . . ?
O2A C31A H31D 109.4 . . ?
C30A C31A H31D 109.4 . . ?
H31C C31A H31D 108.0 . . ?
O2A Li1 O1A 103.2(3) . . ?
O1 Li1 O2 106.2(3) . . ?
O2A Li1 N2 111.6(2) . . ?
O1 Li1 N2 120.0(4) . . ?
O1A Li1 N2 120.7(4) . . ?
O2 Li1 N2 120.27(17) . . ?
O2A Li1 N1 127.4(2) . . ?
O1 Li1 N1 123.4(3) . . ?
O1A Li1 N1 122.4(3) . . ?
O2 Li1 N1 115.67(16) . . ?
N2 Li1 N1 68.05(8) . . ?
O2A Li1 C1 127.6(2) . . ?
O1 Li1 C1 127.7(3) . . ?
O1A Li1 C1 127.5(3) . . ?
O2 Li1 C1 126.07(16) . . ?
N2 Li1 C1 34.06(6) . . ?
N1 Li1 C1 34.06(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
C20 N2 C1 N1 176.26(13) . . . . ?
Li1 N2 C1 N1 4.48(13) . . . . ?
C20 N2 C1 C2 -5.9(2) . . . . ?
Li1 N2 C1 C2 -177.64(12) . . . . ?
C20 N2 C1 Li1 171.78(18) . . . . ?
C16 N1 C1 N2 -178.10(12) . . . . ?
Li1 N1 C1 N2 -4.45(12) . . . . ?
C16 N1 C1 C2 4.00(19) . . . . ?
Li1 N1 C1 C2 177.65(12) . . . . ?
C16 N1 C1 Li1 -173.65(15) . . . . ?
N2 C1 C2 C3 92.98(15) . . . . ?
N1 C1 C2 C3 -89.31(15) . . . . ?
N2 C1 C2 C15 -87.84(15) . . . . ?
N1 C1 C2 C15 89.87(15) . . . . ?
C15 C2 C3 C4 179.26(12) . . . . ?
C1 C2 C3 C4 -1.57(18) . . . . ?
C15 C2 C3 C8 -0.50(18) . . . . ?
C1 C2 C3 C8 178.68(11) . . . . ?
C2 C3 C4 C5 179.85(13) . . . . ?
C8 C3 C4 C5 -0.4(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C4 C5 C6 C7 0.6(2) . . . . ?
C5 C6 C7 C8 -0.1(2) . . . . ?
C6 C7 C8 C9 179.38(14) . . . . ?
C6 C7 C8 C3 -0.7(2) . . . . ?
C2 C3 C8 C9 0.60(19) . . . . ?
C4 C3 C8 C9 -179.17(12) . . . . ?
C2 C3 C8 C7 -179.30(12) . . . . ?
C4 C3 C8 C7 0.93(18) . . . . ?
C7 C8 C9 C10 179.59(13) . . . . ?
C3 C8 C9 C10 -0.30(19) . . . . ?
C8 C9 C10 C11 -179.00(12) . . . . ?
C8 C9 C10 C15 -0.08(19) . . . . ?
C9 C10 C11 C12 178.89(13) . . . . ?
C15 C10 C11 C12 -0.04(19) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C11 C12 C13 C14 -0.3(2) . . . . ?
C12 C13 C14 C15 0.02(19) . . . . ?
C3 C2 C15 C14 179.46(11) . . . . ?
C1 C2 C15 C14 0.27(17) . . . . ?
C3 C2 C15 C10 0.12(17) . . . . ?
C1 C2 C15 C10 -179.07(11) . . . . ?
C13 C14 C15 C2 -179.11(12) . . . . ?
C13 C14 C15 C10 0.24(18) . . . . ?
C9 C10 C15 C2 0.18(18) . . . . ?
C11 C10 C15 C2 179.13(11) . . . . ?
C9 C10 C15 C14 -179.19(11) . . . . ?
C11 C10 C15 C14 -0.23(17) . . . . ?
C1 N1 C16 C18 -159.09(12) . . . . ?
Li1 N1 C16 C18 31.1(2) . . . . ?
C1 N1 C16 C17 -40.50(19) . . . . ?
Li1 N1 C16 C17 149.72(15) . . . . ?
C1 N1 C16 C19 85.27(15) . . . . ?
Li1 N1 C16 C19 -84.51(19) . . . . ?
C1 N2 C20 C23A -148.7(5) . . . . ?
Li1 N2 C20 C23A 18.3(5) . . . . ?
C1 N2 C20 C22A 71.5(5) . . . . ?
Li1 N2 C20 C22A -121.5(5) . . . . ?
C1 N2 C20 C23 -92.38(18) . . . . ?
Li1 N2 C20 C23 74.6(2) . . . . ?
C1 N2 C20 C21 38.0(3) . . . . ?
Li1 N2 C20 C21 -155.0(2) . . . . ?
C1 N2 C20 C22 153.19(15) . . . . ?
Li1 N2 C20 C22 -39.8(2) . . . . ?
C1 N2 C20 C21A -40.6(4) . . . . ?
Li1 N2 C20 C21A 126.4(3) . . . . ?
C27A O1A C24 C25A 20.4(13) . . . . ?
Li1 O1A C24 C25A 170.2(9) . . . . ?
C27 O1 C24 C25 19.6(12) . . . . ?
Li1 O1 C24 C25 165.6(8) . . . . ?
O1 C24 C25 C26 -27.9(11) . . . . ?
O1A C24 C25A C26 -40.2(13) . . . . ?
C24 C25A C26 C27A 43.3(13) . . . . ?
C24 C25 C26 C27 26.5(12) . . . . ?
C24 O1 C27 C26 -2.1(13) . . . . ?
Li1 O1 C27 C26 -145.9(8) . . . . ?
C25 C26 C27 O1 -15.7(13) . . . . ?
C24 O1A C27A C26 8.0(13) . . . . ?
Li1 O1A C27A C26 -139.6(9) . . . . ?
C25A C26 C27A O1A -32.5(13) . . . . ?
C31 O2 C28 C29 25.4(6) . . . . ?
Li1 O2 C28 C29 -156.7(5) . . . . ?
C31A O2A C28A C29A -36.7(8) . . . . ?
Li1 O2A C28A C29A 142.7(7) . . . . ?
O2 C28 C29 C30 -14.2(9) . . . . ?
O2A C28A C29A C30A 28.6(12) . . . . ?
C28 C29 C30 C31 -0.1(9) . . . . ?
C28A C29A C30A C31A -11.2(13) . . . . ?
C28 O2 C31 C30 -26.3(6) . . . . ?
Li1 O2 C31 C30 156.6(6) . . . . ?
C29 C30 C31 O2 16.4(9) . . . . ?
C28A O2A C31A C30A 29.9(10) . . . . ?
Li1 O2A C31A C30A -149.2(9) . . . . ?
C29A C30A C31A O2A -11.2(14) . . . . ?

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_3-BF2
_database_code_depnum_ccdc_archive 'CCDC 2302137'
loop_
_audit_author_name
_audit_author_address
'Ramkumar Kannan'
;Tata Institute of Fundamental Research Hyderabad
India
;
_audit_update_record             
;
2023-10-20 deposited with the CCDC.	2023-10-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_RINTA01_3-BF2               
;
RESPONSE: This alerts are due to the quality
of the crystal. On repeated crystallisation and data 
collection we could not get better data sets.
;
_vrf_PLAT020_3-BF2               
;
RESPONSE: This alerts are due to the quality
of the crystal. On repeated crystallisation and data 
collection we could not get better data sets.

;
# end Validation Reply Form

_audit_creation_date             2023-10-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H27 B F2 N2'
_chemical_formula_sum            'C23 H27 B F2 N2'
_chemical_formula_weight         380.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   11.8480(9)
_cell_length_b                   9.1474(6)
_cell_length_c                   20.2739(13)
_cell_angle_alpha                90
_cell_angle_beta                 102.996(7)
_cell_angle_gamma                90
_cell_volume                     2141.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7360
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3490
_cell_measurement_theta_min      3.0290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1940
_diffrn_reflns_av_unetI/netI     0.0902
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            20843
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.841
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2490
_reflns_number_total             3702
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3702
_refine_ls_number_restraints     129
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0806
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1544P)²+0.1759P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2361
_refine_ls_wR_factor_ref         0.2596
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C20-C21 \\sim C20-C21A
 with sigma of 0.02
 C20-C22 \\sim C20-C22A
 with sigma of 0.02
 C20-C23 \\sim C20-C23A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C20 \\sim C21 \\sim C22 \\sim C23: within 3A with sigma of 0.02 and sigma for
terminal atoms of 0.04 within 3A
C20 \\sim C21 \\sim C22 \\sim C23 \\sim C21A \\sim C22A \\sim C23A: within 3A
with sigma of 0.02 and sigma for terminal atoms of 0.04 within 3A
4. Others
 Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C22A)=Sof(H22D)=Sof(H22E)=
 Sof(H22F)=Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=1-FVAR(1)
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=
 Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C13(H13), C6(H6), C11(H11), C3(H3), C10(H10), C4(H4), C8(H8), C9(H9)
5.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C17(H17A,H17B,H17C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C21A(H21D,H21E,H21F),
 C22A(H22D,H22E,H22F), C23A(H23D,H23E,H23F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.52236(18) -0.0607(2) 0.90834(10) 0.0901(7) Uani 1 1 d . . . . .
F1 F 0.68865(16) 0.0301(3) 0.89517(11) 0.0957(8) Uani 1 1 d . . . . .
N1 N 0.5181(2) 0.1888(3) 0.85702(11) 0.0637(7) Uani 1 1 d . . . . .
N2 N 0.5297(3) 0.0223(3) 0.79227(12) 0.0661(8) Uani 1 1 d . . . . .
C2 C 0.4422(2) 0.2536(3) 0.73367(13) 0.0478(7) Uani 1 1 d . . . . .
C5 C 0.3398(2) 0.4387(3) 0.62654(14) 0.0505(7) Uani 1 1 d . . . . .
C12 C 0.4841(2) 0.6147(3) 0.56581(13) 0.0506(7) Uani 1 1 d . . . . .
C1 C 0.4947(2) 0.1591(3) 0.79209(12) 0.0454(7) Uani 1 1 d . . . . .
C14 C 0.4632(2) 0.4315(3) 0.64877(12) 0.0451(7) Uani 1 1 d . . . . .
C15 C 0.5102(2) 0.3357(3) 0.70311(13) 0.0479(7) Uani 1 1 d . . . . .
H15 H 0.590249 0.329348 0.718084 0.058 Uiso 1 1 calc R U . . .
C7 C 0.3602(3) 0.6237(3) 0.54405(13) 0.0534(7) Uani 1 1 d . . . . .
C13 C 0.5321(2) 0.5174(3) 0.61726(13) 0.0500(7) Uani 1 1 d . . . . .
H13 H 0.612229 0.509781 0.630858 0.060 Uiso 1 1 calc R U . . .
C6 C 0.2921(2) 0.5346(3) 0.57417(14) 0.0570(8) Uani 1 1 d . . . . .
H6 H 0.211997 0.538619 0.559055 0.068 Uiso 1 1 calc R U . . .
C16 C 0.5147(3) 0.3249(3) 0.89556(15) 0.0600(8) Uani 1 1 d . . . . .
C11 C 0.5537(3) 0.7056(3) 0.53444(15) 0.0613(8) Uani 1 1 d . . . . .
H11 H 0.633937 0.698680 0.547332 0.074 Uiso 1 1 calc R U . . .
C3 C 0.3191(2) 0.2591(3) 0.71068(15) 0.0587(8) Uani 1 1 d . . . . .
H3 H 0.272340 0.201397 0.731329 0.070 Uiso 1 1 calc R U . . .
C10 C 0.5039(3) 0.8032(3) 0.48541(16) 0.0705(9) Uani 1 1 d . . . . .
H10 H 0.550073 0.862559 0.465114 0.085 Uiso 1 1 calc R U . . .
C4 C 0.2709(2) 0.3481(3) 0.65893(15) 0.0601(8) Uani 1 1 d . . . . .
H4 H 0.190693 0.350317 0.644075 0.072 Uiso 1 1 calc R U . . .
C8 C 0.3126(3) 0.7269(3) 0.49264(15) 0.0667(9) Uani 1 1 d . . . . .
H8 H 0.232670 0.734337 0.477574 0.080 Uiso 1 1 calc R U . . .
C20 C 0.5367(3) -0.0822(3) 0.73886(15) 0.0635(8) Uani 1 1 d D U . . .
C9 C 0.3820(3) 0.8133(3) 0.46575(17) 0.0747(10) Uani 1 1 d . . . . .
H9 H 0.348865 0.881861 0.433250 0.090 Uiso 1 1 calc R U . . .
B1 B 0.5723(3) 0.0326(4) 0.87102(16) 0.0524(8) Uani 1 1 d . . . . .
C18 C 0.6055(4) 0.4275(4) 0.8841(2) 0.0973(13) Uani 1 1 d . . . . .
H18A H 0.678790 0.378109 0.892453 0.146 Uiso 1 1 calc R U . . .
H18B H 0.610227 0.509275 0.914305 0.146 Uiso 1 1 calc R U . . .
H18C H 0.586093 0.461581 0.838146 0.146 Uiso 1 1 calc R U . . .
C19 C 0.5395(4) 0.2802(4) 0.96979(17) 0.1020(14) Uani 1 1 d . . . . .
H19A H 0.483279 0.209395 0.976399 0.153 Uiso 1 1 calc R U . . .
H19B H 0.535257 0.364643 0.997251 0.153 Uiso 1 1 calc R U . . .
H19C H 0.615637 0.238413 0.982508 0.153 Uiso 1 1 calc R U . . .
C17 C 0.3942(3) 0.3913(5) 0.8763(2) 0.1050(15) Uani 1 1 d . . . . .
H17A H 0.380114 0.426837 0.830604 0.157 Uiso 1 1 calc R U . . .
H17B H 0.388744 0.470794 0.906315 0.157 Uiso 1 1 calc R U . . .
H17C H 0.337713 0.318200 0.879746 0.157 Uiso 1 1 calc R U . . .
C21 C 0.6387(5) -0.0402(8) 0.7106(4) 0.097(2) Uani 0.801(9) 1 d D U P A 1
H21A H 0.623049 0.050830 0.686739 0.146 Uiso 0.801(9) 1 calc R U P A 1
H21B H 0.652517 -0.114811 0.680025 0.146 Uiso 0.801(9) 1 calc R U P A 1
H21C H 0.705963 -0.029799 0.746896 0.146 Uiso 0.801(9) 1 calc R U P A 1
C22 C 0.4258(4) -0.0818(7) 0.6836(3) 0.101(2) Uani 0.801(9) 1 d D U P A 1
H22A H 0.360122 -0.088243 0.703844 0.152 Uiso 0.801(9) 1 calc R U P A 1
H22B H 0.425979 -0.163960 0.654140 0.152 Uiso 0.801(9) 1 calc R U P A 1
H22C H 0.421408 0.007046 0.657928 0.152 Uiso 0.801(9) 1 calc R U P A 1
C23 C 0.5543(9) -0.2308(5) 0.7728(3) 0.115(3) Uani 0.801(9) 1 d D U P A 1
H23A H 0.622039 -0.228449 0.809114 0.172 Uiso 0.801(9) 1 calc R U P A 1
H23B H 0.564031 -0.303322 0.740280 0.172 Uiso 0.801(9) 1 calc R U P A 1
H23C H 0.487870 -0.254776 0.790425 0.172 Uiso 0.801(9) 1 calc R U P A 1
C21A C 0.641(2) -0.188(3) 0.7636(15) 0.108(7) Uani 0.199(9) 1 d D U P A 2
H21D H 0.708253 -0.149958 0.750825 0.162 Uiso 0.199(9) 1 calc R U P A 2
H21E H 0.622368 -0.282437 0.743339 0.162 Uiso 0.199(9) 1 calc R U P A 2
H21F H 0.655774 -0.197021 0.812010 0.162 Uiso 0.199(9) 1 calc R U P A 2
C22A C 0.587(3) -0.032(4) 0.6796(13) 0.110(7) Uani 0.199(9) 1 d D U P A 2
H22D H 0.527032 0.011885 0.645571 0.165 Uiso 0.199(9) 1 calc R U P A 2
H22E H 0.618992 -0.114024 0.660789 0.165 Uiso 0.199(9) 1 calc R U P A 2
H22F H 0.647051 0.039031 0.695380 0.165 Uiso 0.199(9) 1 calc R U P A 2
C23A C 0.4320(17) -0.177(3) 0.7286(15) 0.106(6) Uani 0.199(9) 1 d D U P A 2
H23D H 0.385490 -0.148928 0.759596 0.159 Uiso 0.199(9) 1 calc R U P A 2
H23E H 0.455449 -0.277428 0.736686 0.159 Uiso 0.199(9) 1 calc R U P A 2
H23F H 0.387750 -0.166889 0.683005 0.159 Uiso 0.199(9) 1 calc R U P A 2


_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
F2 B1 1.361(4) . ?
F1 B1 1.356(4) . ?
N1 C1 1.312(3) . ?
N1 C16 1.475(4) . ?
N1 B1 1.566(4) . ?
N2 C1 1.317(3) . ?
N2 C20 1.461(4) . ?
N2 B1 1.565(4) . ?
C2 C1 1.486(3) . ?
C2 C15 1.350(4) . ?
C2 C3 1.428(4) . ?
C5 C14 1.431(4) . ?
C5 C6 1.395(4) . ?
C5 C4 1.423(4) . ?
C12 C7 1.437(4) . ?
C12 C13 1.392(4) . ?
C12 C11 1.418(4) . ?
C14 C15 1.420(4) . ?
C14 C13 1.388(4) . ?
C15 H15 0.9300 . ?
C7 C6 1.382(4) . ?
C7 C8 1.425(4) . ?
C13 H13 0.9300 . ?
C6 H6 0.9300 . ?
C16 C18 1.485(5) . ?
C16 C19 1.523(5) . ?
C16 C17 1.519(5) . ?
C11 H11 0.9300 . ?
C11 C10 1.367(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.349(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.413(5) . ?
C4 H4 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.342(5) . ?
C20 C21 1.499(7) . ?
C20 C22 1.523(6) . ?
C20 C23 1.517(6) . ?
C20 C21A 1.559(16) . ?
C20 C22A 1.528(18) . ?
C20 C23A 1.491(16) . ?
C9 H9 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C21A H21D 0.9600 . ?
C21A H21E 0.9600 . ?
C21A H21F 0.9600 . ?
C22A H22D 0.9600 . ?
C22A H22E 0.9600 . ?
C22A H22F 0.9600 . ?
C23A H23D 0.9600 . ?
C23A H23E 0.9600 . ?
C23A H23F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C16 133.0(2) . . ?
C1 N1 B1 88.7(2) . . ?
C16 N1 B1 137.1(2) . . ?
C1 N2 C20 133.6(2) . . ?
C1 N2 B1 88.6(2) . . ?
C20 N2 B1 137.4(2) . . ?
C15 C2 C1 120.2(2) . . ?
C15 C2 C3 120.1(2) . . ?
C3 C2 C1 119.6(2) . . ?
C6 C5 C14 118.6(3) . . ?
C6 C5 C4 122.8(3) . . ?
C4 C5 C14 118.6(2) . . ?
C13 C12 C7 118.9(3) . . ?
C13 C12 C11 122.0(3) . . ?
C11 C12 C7 119.1(2) . . ?
N1 C1 N2 101.5(2) . . ?
N1 C1 C2 129.4(2) . . ?
N2 C1 C2 129.1(2) . . ?
C15 C14 C5 117.9(2) . . ?
C13 C14 C5 119.6(2) . . ?
C13 C14 C15 122.5(2) . . ?
C2 C15 C14 121.9(2) . . ?
C2 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C6 C7 C12 119.2(2) . . ?
C6 C7 C8 122.7(3) . . ?
C8 C7 C12 118.1(3) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 C12 121.6(3) . . ?
C14 C13 H13 119.2 . . ?
C5 C6 H6 119.0 . . ?
C7 C6 C5 122.0(3) . . ?
C7 C6 H6 119.0 . . ?
N1 C16 C18 110.1(3) . . ?
N1 C16 C19 105.9(3) . . ?
N1 C16 C17 109.7(3) . . ?
C18 C16 C19 109.8(3) . . ?
C18 C16 C17 112.3(3) . . ?
C17 C16 C19 108.8(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 C12 120.6(3) . . ?
C10 C11 H11 119.7 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C11 C10 H10 120.2 . . ?
C11 C10 C9 119.6(3) . . ?
C9 C10 H10 120.2 . . ?
C5 C4 H4 119.2 . . ?
C3 C4 C5 121.6(3) . . ?
C3 C4 H4 119.2 . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.7 . . ?
N2 C20 C21 107.5(4) . . ?
N2 C20 C22 111.1(3) . . ?
N2 C20 C23 106.0(3) . . ?
N2 C20 C21A 109.9(9) . . ?
N2 C20 C22A 118.8(12) . . ?
N2 C20 C23A 107.5(9) . . ?
C21 C20 C22 110.8(4) . . ?
C21 C20 C23 111.3(5) . . ?
C23 C20 C22 110.1(4) . . ?
C22A C20 C21A 91.2(18) . . ?
C23A C20 C21A 104.8(16) . . ?
C23A C20 C22A 121.8(16) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 C10 121.9(3) . . ?
C8 C9 H9 119.1 . . ?
F2 B1 N1 117.5(3) . . ?
F2 B1 N2 116.7(2) . . ?
F1 B1 F2 108.8(2) . . ?
F1 B1 N1 115.0(3) . . ?
F1 B1 N2 115.8(3) . . ?
N2 B1 N1 81.10(19) . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C21A H21D 109.5 . . ?
C20 C21A H21E 109.5 . . ?
C20 C21A H21F 109.5 . . ?
H21D C21A H21E 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
C20 C22A H22D 109.5 . . ?
C20 C22A H22E 109.5 . . ?
C20 C22A H22F 109.5 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
C20 C23A H23D 109.5 . . ?
C20 C23A H23E 109.5 . . ?
C20 C23A H23F 109.5 . . ?
H23D C23A H23E 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 C4 C5 -0.5(4) . . . . ?
C5 C14 C15 C2 -0.2(4) . . . . ?
C5 C14 C13 C12 2.2(4) . . . . ?
C12 C7 C6 C5 1.9(4) . . . . ?
C12 C7 C8 C9 -0.3(4) . . . . ?
C12 C11 C10 C9 -0.1(4) . . . . ?
C1 N1 C16 C18 -67.4(4) . . . . ?
C1 N1 C16 C19 173.9(3) . . . . ?
C1 N1 C16 C17 56.6(5) . . . . ?
C1 N1 B1 F2 -118.1(3) . . . . ?
C1 N1 B1 F1 111.8(3) . . . . ?
C1 N1 B1 N2 -2.6(2) . . . . ?
C1 N2 C20 C21 75.6(5) . . . . ?
C1 N2 C20 C22 -45.7(6) . . . . ?
C1 N2 C20 C23 -165.3(5) . . . . ?
C1 N2 C20 C21A 148.6(15) . . . . ?
C1 N2 C20 C22A 45.7(17) . . . . ?
C1 N2 C20 C23A -97.9(14) . . . . ?
C1 N2 B1 F2 119.0(3) . . . . ?
C1 N2 B1 F1 -111.0(3) . . . . ?
C1 N2 B1 N1 2.6(2) . . . . ?
C1 C2 C15 C14 -177.7(2) . . . . ?
C1 C2 C3 C4 178.0(3) . . . . ?
C14 C5 C6 C7 -1.0(4) . . . . ?
C14 C5 C4 C3 1.6(4) . . . . ?
C15 C2 C1 N1 91.1(4) . . . . ?
C15 C2 C1 N2 -89.3(4) . . . . ?
C15 C2 C3 C4 -1.0(4) . . . . ?
C15 C14 C13 C12 -177.5(2) . . . . ?
C7 C12 C13 C14 -1.3(4) . . . . ?
C7 C12 C11 C10 1.7(4) . . . . ?
C7 C8 C9 C10 2.0(5) . . . . ?
C13 C12 C7 C6 -0.7(4) . . . . ?
C13 C12 C7 C8 178.3(2) . . . . ?
C13 C12 C11 C10 -178.1(3) . . . . ?
C13 C14 C15 C2 179.4(2) . . . . ?
C6 C5 C14 C15 178.6(2) . . . . ?
C6 C5 C14 C13 -1.0(4) . . . . ?
C6 C5 C4 C3 -178.2(3) . . . . ?
C6 C7 C8 C9 178.7(3) . . . . ?
C16 N1 C1 N2 172.2(3) . . . . ?
C16 N1 C1 C2 -8.1(5) . . . . ?
C16 N1 B1 F2 73.6(4) . . . . ?
C16 N1 B1 F1 -56.5(5) . . . . ?
C16 N1 B1 N2 -170.9(4) . . . . ?
C11 C12 C7 C6 179.5(2) . . . . ?
C11 C12 C7 C8 -1.5(4) . . . . ?
C11 C12 C13 C14 178.4(2) . . . . ?
C11 C10 C9 C8 -1.7(5) . . . . ?
C3 C2 C1 N1 -87.9(4) . . . . ?
C3 C2 C1 N2 91.7(4) . . . . ?
C3 C2 C15 C14 1.3(4) . . . . ?
C4 C5 C14 C15 -1.2(4) . . . . ?
C4 C5 C14 C13 179.1(2) . . . . ?
C4 C5 C6 C7 178.8(3) . . . . ?
C8 C7 C6 C5 -177.1(3) . . . . ?
C20 N2 C1 N1 -176.5(3) . . . . ?
C20 N2 C1 C2 3.8(5) . . . . ?
C20 N2 B1 F2 -68.1(5) . . . . ?
C20 N2 B1 F1 61.9(5) . . . . ?
C20 N2 B1 N1 175.5(4) . . . . ?
B1 N1 C1 N2 3.1(3) . . . . ?
B1 N1 C1 C2 -177.2(3) . . . . ?
B1 N1 C16 C18 96.4(4) . . . . ?
B1 N1 C16 C19 -22.2(5) . . . . ?
B1 N1 C16 C17 -139.6(4) . . . . ?
B1 N2 C1 N1 -3.1(3) . . . . ?
B1 N2 C1 C2 177.2(3) . . . . ?
B1 N2 C20 C21 -94.5(5) . . . . ?
B1 N2 C20 C22 144.1(5) . . . . ?
B1 N2 C20 C23 24.6(6) . . . . ?
B1 N2 C20 C21A -21.5(16) . . . . ?
B1 N2 C20 C22A -124.5(17) . . . . ?
B1 N2 C20 C23A 92.0(14) . . . . ?

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

data_4-BF2
_database_code_depnum_ccdc_archive 'CCDC 2302136'
loop_
_audit_author_name
_audit_author_address
'Ramkumar Kannan'
;Tata Institute of Fundamental Research Hyderabad
India
;
_audit_update_record             
;
2023-10-19 deposited with the CCDC.	2023-10-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT911_4-BF2               
;
RESPONSE: These reflections were probably affected by unexpected deviations
in their intensities for symmetry equivalent measurements and omitted during
initial data reduction.
;

# end Validation Reply Form

_audit_creation_date             2023-10-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H27 B F2 N2'
_chemical_formula_sum            'C23 H27 B F2 N2'
_chemical_formula_weight         380.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.8124(11)
_cell_length_b                   10.4197(7)
_cell_length_c                   13.3309(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.223(2)
_cell_angle_gamma                90
_cell_volume                     2041.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.02
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.705
_diffrn_reflns_Laue_measured_fraction_max 0.757
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12537
_diffrn_reflns_point_group_measured_fraction_full 0.705
_diffrn_reflns_point_group_measured_fraction_max 0.757
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.031
_diffrn_reflns_theta_min         2.396
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.705
_diffrn_measured_fraction_theta_max 0.757
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2044
_reflns_number_total             2264
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2264
_refine_ls_number_restraints     129
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0684
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0688P)²+1.8955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1751
_refine_ls_wR_factor_ref         0.1787
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C10-C11 \\sim C10-C11A
 with sigma of 0.02
 C10-C12 \\sim C10-C12A
 with sigma of 0.02
 C10-C13 \\sim C10-C13A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C10 \\sim C11 \\sim C12 \\sim C13 \\sim C11A \\sim C12A \\sim C13A: within 3A
with sigma of 0.02 and sigma for terminal atoms of 0.04 within 3A
4. Others
 Sof(C11A)=Sof(H11D)=Sof(H11E)=Sof(H11F)=Sof(C12A)=Sof(H12D)=Sof(H12E)=
 Sof(H12F)=Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=1-FVAR(1)
 Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(H11C)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7)
5.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C11A(H11D,H11E,
 H11F), C12A(H12D,H12E,H12F), C13A(H13D,H13E,H13F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.08613(10) 0.55869(18) 0.42025(12) 0.0302(4) Uani 1 1 d . . . . .
H1 H 0.086297 0.649861 0.420381 0.036 Uiso 1 1 calc R U . . .
C2 C 0.12709(12) 0.4939(2) 0.50157(13) 0.0365(4) Uani 1 1 d . . . . .
H2 H 0.155773 0.540013 0.558275 0.044 Uiso 1 1 calc R U . . .
C3 C 0.12761(11) 0.3575(2) 0.50293(12) 0.0346(4) Uani 1 1 d . . . . .
H3 H 0.156640 0.313569 0.560601 0.042 Uiso 1 1 calc R U . . .
C4 C 0.08686(10) 0.28869(17) 0.42227(11) 0.0264(3) Uani 1 1 d . . . . .
H4 H 0.087800 0.197555 0.424329 0.032 Uiso 1 1 calc R U . . .
C5 C 0.04290(8) 0.35326(15) 0.33495(10) 0.0193(3) Uani 1 1 d . . . . .
C6 C 0.04252(9) 0.49071(15) 0.33399(10) 0.0216(3) Uani 1 1 d . . . . .
C7 C 0.000000 0.5564(2) 0.250000 0.0242(4) Uani 1 2 d S T P . .
H7 H -0.000002 0.647595 0.250000 0.029 Uiso 1 2 calc R U P . .
C8 C 0.000000 0.28641(19) 0.250000 0.0173(4) Uani 1 2 d S T P . .
C9 C 0.000000 0.14455(19) 0.250000 0.0188(4) Uani 1 2 d S T P . .
C10 C 0.14560(9) 0.07677(16) 0.17659(12) 0.0260(3) Uani 1 1 d D U . . .
C11 C 0.1169(2) 0.0833(4) 0.0649(2) 0.0376(8) Uani 0.552(3) 1 d D U P A 1
H11A H 0.170913 0.086610 0.029473 0.056 Uiso 0.552(3) 1 calc R U P A 1
H11B H 0.080035 0.160520 0.049004 0.056 Uiso 0.552(3) 1 calc R U P A 1
H11C H 0.080825 0.007126 0.043157 0.056 Uiso 0.552(3) 1 calc R U P A 1
C12 C 0.2027(2) -0.0445(4) 0.2050(3) 0.0410(9) Uani 0.552(3) 1 d D U P A 1
H12A H 0.165383 -0.120980 0.188112 0.061 Uiso 0.552(3) 1 calc R U P A 1
H12B H 0.223729 -0.043824 0.277736 0.061 Uiso 0.552(3) 1 calc R U P A 1
H12C H 0.255414 -0.045848 0.167319 0.061 Uiso 0.552(3) 1 calc R U P A 1
C13 C 0.2026(2) 0.1954(4) 0.2127(3) 0.0392(8) Uani 0.552(3) 1 d D U P A 1
H13A H 0.259381 0.195115 0.182066 0.059 Uiso 0.552(3) 1 calc R U P A 1
H13B H 0.216658 0.193056 0.286509 0.059 Uiso 0.552(3) 1 calc R U P A 1
H13C H 0.168079 0.273385 0.192536 0.059 Uiso 0.552(3) 1 calc R U P A 1
B1 B 0.000000 -0.0513(2) 0.250000 0.0267(5) Uani 1 2 d S T P . .
F1 F -0.03721(11) -0.12572(13) 0.17115(11) 0.0581(4) Uani 1 1 d . . . . .
N1 N 0.06032(10) 0.06368(14) 0.22119(14) 0.0381(4) Uani 1 1 d . . . . .
C11A C 0.1515(3) 0.1936(5) 0.1082(4) 0.0454(12) Uani 0.448(3) 1 d D U P A 2
H11D H 0.209203 0.191392 0.079395 0.068 Uiso 0.448(3) 1 calc R U P A 2
H11E H 0.148423 0.272227 0.147913 0.068 Uiso 0.448(3) 1 calc R U P A 2
H11F H 0.100738 0.191881 0.053476 0.068 Uiso 0.448(3) 1 calc R U P A 2
C12A C 0.1588(3) -0.0451(5) 0.1159(5) 0.0534(15) Uani 0.448(3) 1 d D U P A 2
H12D H 0.116513 -0.044321 0.053192 0.080 Uiso 0.448(3) 1 calc R U P A 2
H12E H 0.147002 -0.120587 0.156083 0.080 Uiso 0.448(3) 1 calc R U P A 2
H12F H 0.221503 -0.048293 0.099604 0.080 Uiso 0.448(3) 1 calc R U P A 2
C13A C 0.2158(3) 0.0844(6) 0.2679(3) 0.0464(12) Uani 0.448(3) 1 d D U P A 2
H13D H 0.276709 0.083077 0.246625 0.070 Uiso 0.448(3) 1 calc R U P A 2
H13E H 0.208865 0.010833 0.312178 0.070 Uiso 0.448(3) 1 calc R U P A 2
H13F H 0.207536 0.164122 0.304669 0.070 Uiso 0.448(3) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9500 . ?
C1 C2 1.354(3) . ?
C1 C6 1.4334(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.421(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.368(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.4287(19) . ?
C5 C6 1.432(2) . ?
C5 C8 1.4108(16) . ?
C6 C7 1.3935(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.478(3) . ?
C9 N1 1.3199(18) . ?
C9 N1 1.3198(18) 2 ?
C10 C11 1.498(3) . ?
C10 C12 1.542(3) . ?
C10 C13 1.539(4) . ?
C10 N1 1.4687(19) . ?
C10 C11A 1.530(4) . ?
C10 C12A 1.531(5) . ?
C10 C13A 1.500(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
B1 B1 0.000(5) 2 ?
B1 F1 1.3655(18) 2 ?
B1 F1 1.3655(18) . ?
B1 N1 1.571(2) 2 ?
B1 N1 1.571(2) . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 0.9800 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?
C13A H13D 0.9800 . ?
C13A H13E 0.9800 . ?
C13A H13F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.46(17) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.67(15) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.86(16) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.29(16) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 118.63(13) . . ?
C8 C5 C4 122.32(14) . . ?
C8 C5 C6 119.05(13) . . ?
C5 C6 C1 119.09(14) . . ?
C7 C6 C1 120.95(16) . . ?
C7 C6 C5 119.96(14) . . ?
C6 C7 C6 121.14(19) . 2 ?
C6 C7 H7 119.4 2 . ?
C6 C7 H7 119.4 . . ?
C5 C8 C5 120.84(18) . 2 ?
C5 C8 C9 119.58(9) 2 . ?
C5 C8 C9 119.58(9) . . ?
N1 C9 C8 129.68(9) 2 . ?
N1 C9 C8 129.68(9) . . ?
N1 C9 N1 100.65(19) 2 . ?
C11 C10 C12 111.1(2) . . ?
C11 C10 C13 110.5(2) . . ?
C13 C10 C12 108.6(2) . . ?
N1 C10 C11 104.78(17) . . ?
N1 C10 C12 107.33(17) . . ?
N1 C10 C13 114.45(17) . . ?
N1 C10 C11A 115.59(18) . . ?
N1 C10 C12A 108.1(2) . . ?
N1 C10 C13A 102.7(2) . . ?
C11A C10 C12A 108.9(3) . . ?
C13A C10 C11A 110.9(3) . . ?
C13A C10 C12A 110.5(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
B1 B1 F1 0(10) 2 2 ?
B1 B1 F1 0(10) 2 . ?
B1 B1 N1 0(10) 2 . ?
B1 B1 N1 0(10) 2 2 ?
F1 B1 F1 110.8(2) 2 . ?
F1 B1 N1 115.59(10) . . ?
F1 B1 N1 115.59(10) 2 2 ?
F1 B1 N1 115.75(10) 2 . ?
F1 B1 N1 115.75(10) . 2 ?
N1 B1 N1 80.60(15) 2 . ?
B1 F1 B1 0.0 2 . ?
C9 N1 C10 134.96(15) . . ?
C9 N1 B1 89.38(12) . 2 ?
C9 N1 B1 89.38(12) . . ?
C10 N1 B1 135.61(13) . 2 ?
C10 N1 B1 135.61(13) . . ?
B1 N1 B1 0.00(12) 2 . ?
C10 C11A H11D 109.5 . . ?
C10 C11A H11E 109.5 . . ?
C10 C11A H11F 109.5 . . ?
H11D C11A H11E 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
C10 C12A H12D 109.5 . . ?
C10 C12A H12E 109.5 . . ?
C10 C12A H12F 109.5 . . ?
H12D C12A H12E 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
C10 C13A H13D 109.5 . . ?
C10 C13A H13E 109.5 . . ?
C10 C13A H13F 109.5 . . ?
H13D C13A H13E 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.0(3) . . . . ?
C1 C6 C7 C6 -179.96(13) . . . 2 ?
C2 C1 C6 C5 0.0(2) . . . . ?
C2 C1 C6 C7 179.86(12) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C3 C4 C5 C8 179.99(12) . . . . ?
C4 C5 C6 C1 0.04(18) . . . . ?
C4 C5 C6 C7 -179.85(10) . . . . ?
C4 C5 C8 C5 179.92(13) . . . 2 ?
C4 C5 C8 C9 -0.08(13) . . . . ?
C5 C6 C7 C6 -0.07(8) . . . 2 ?
C5 C8 C9 N1 -88.33(12) 2 . . 2 ?
C5 C8 C9 N1 91.67(12) 2 . . . ?
C5 C8 C9 N1 -88.33(12) . . . . ?
C5 C8 C9 N1 91.67(12) . . . 2 ?
C6 C1 C2 C3 0.0(2) . . . . ?
C6 C5 C8 C5 -0.07(8) . . . 2 ?
C6 C5 C8 C9 179.93(8) . . . . ?
C8 C5 C6 C1 -179.97(10) . . . . ?
C8 C5 C6 C7 0.14(16) . . . . ?
C8 C9 N1 C10 -2.5(3) . . . . ?
C8 C9 N1 B1 180.000(0) . . . 2 ?
C8 C9 N1 B1 180.000(0) . . . . ?
C11 C10 N1 C9 -86.8(3) . . . . ?
C11 C10 N1 B1 89.7(3) . . . . ?
C11 C10 N1 B1 89.7(3) . . . 2 ?
C12 C10 N1 C9 155.0(2) . . . . ?
C12 C10 N1 B1 -28.5(3) . . . . ?
C12 C10 N1 B1 -28.5(3) . . . 2 ?
C13 C10 N1 C9 34.4(3) . . . . ?
C13 C10 N1 B1 -149.1(2) . . . 2 ?
C13 C10 N1 B1 -149.1(2) . . . . ?
B1 B1 N1 C9 0(100) 2 . . . ?
B1 B1 N1 C10 0.00(4) 2 . . . ?
F1 B1 F1 B1 0(100) 2 . . 2 ?
F1 B1 N1 C9 -113.97(14) 2 . . . ?
F1 B1 N1 C9 114.14(14) . . . . ?
F1 B1 N1 C10 -63.3(2) . . . . ?
F1 B1 N1 C10 68.5(2) 2 . . . ?
F1 B1 N1 B1 0(100) . . . 2 ?
F1 B1 N1 B1 0(35) 2 . . 2 ?
N1 C9 N1 C10 177.5(3) 2 . . . ?
N1 C9 N1 B1 0.000(0) 2 . . 2 ?
N1 C9 N1 B1 0.000(0) 2 . . . ?
N1 B1 F1 B1 0(2) . . . 2 ?
N1 B1 F1 B1 0(81) 2 . . 2 ?
N1 B1 N1 C9 0.000(0) 2 . . . ?
N1 B1 N1 C10 -177.5(3) 2 . . . ?
N1 B1 N1 B1 0(100) 2 . . 2 ?
C11A C10 N1 C9 -30.8(4) . . . . ?
C11A C10 N1 B1 145.6(3) . . . 2 ?
C11A C10 N1 B1 145.6(3) . . . . ?
C12A C10 N1 C9 -153.1(3) . . . . ?
C12A C10 N1 B1 23.3(4) . . . . ?
C12A C10 N1 B1 23.3(4) . . . 2 ?
C13A C10 N1 C9 90.0(3) . . . . ?
C13A C10 N1 B1 -93.5(3) . . . 2 ?
C13A C10 N1 B1 -93.5(3) . . . . ?

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

data_2-BF2
_database_code_depnum_ccdc_archive 'CCDC 2302141'
loop_
_audit_author_name
_audit_author_address
'Ramkumar Kannan'
;Tata Institute of Fundamental Research Hyderabad
India
;
_audit_update_record             
;
2023-10-20 deposited with the CCDC.	2023-10-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_RINTA01_2-BF2               
;
RESPONSE: This alerts are due to the quality
of the crystal. On repeated crystallisation and data 
collection we could not get better data sets.
;
_vrf_PLAT020_2-BF2               
;
RESPONSE: This alerts are due to the quality
of the crystal. On repeated crystallisation and data 
collection we could not get better data sets.

;
# end Validation Reply Form

_audit_creation_date             2023-10-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H25 B F2 N2'
_chemical_formula_sum            'C19 H25 B F2 N2'
_chemical_formula_weight         330.22
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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'
'-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                   9.101(3)
_cell_length_b                   22.767(7)
_cell_length_c                   37.013(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7669(4)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9118
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.03
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             2816
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1859
_diffrn_reflns_av_unetI/netI     0.1027
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            166852
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.100
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3382
_reflns_number_total             6745
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     558
_refine_ls_number_reflns         6745
_refine_ls_number_restraints     516
_refine_ls_R_factor_all          0.1880
_refine_ls_R_factor_gt           0.1061
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0648P)²+12.4043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2389
_refine_ls_wR_factor_ref         0.2858
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C31-C34 \\sim C31-C34A
 with sigma of 0.02
 C12-C14 \\sim C12-C14A
 with sigma of 0.02
 C31-C33 \\sim C31-C33A
 with sigma of 0.02
 C31-C32 \\sim C31-C32A
 with sigma of 0.02
 C12-C15 \\sim C12-C15A
 with sigma of 0.02
 C12-C13 \\sim C12-C13A
 with sigma of 0.02
 C17-C18 \\sim C17-C18A
 with sigma of 0.02
 C17-C16 \\sim C17-C16A
 with sigma of 0.02
 C35-C38 \\sim C35-C38A
 with sigma of 0.02
 C17-C19 \\sim C17-C19A
 with sigma of 0.02
 C35-C36 \\sim C35-C36A
 with sigma of 0.02
 C35-C37 \\sim C35-C37A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C17 \\sim C18 \\sim C19 \\sim C16 \\sim C18A \\sim C16A \\sim C19A: within 3A
with sigma of 0.02 and sigma for terminal atoms of 0.04 within 3A
C31 \\sim C34 \\sim C33 \\sim C32 \\sim C32A \\sim C33A \\sim C34A: within 3A
with sigma of 0.02 and sigma for terminal atoms of 0.04 within 3A
C35 \\sim C38 \\sim C36 \\sim C37 \\sim C36A \\sim C37A \\sim C38A: within 3A
with sigma of 0.02 and sigma for terminal atoms of 0.04 within 3A
C12 \\sim C13 \\sim C14 \\sim C15 \\sim C13A \\sim C14A \\sim C15A: within 3A
with sigma of 0.02 and sigma for terminal atoms of 0.04 within 3A
4. Others
 Sof(C32A)=Sof(H32D)=Sof(H32E)=Sof(H32F)=Sof(C33A)=Sof(H33D)=Sof(H33E)=
 Sof(H33F)=Sof(C34A)=Sof(H34D)=Sof(H34E)=Sof(H34F)=1-FVAR(1)
 Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(H32C)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(H33C)=
 Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(H34C)=FVAR(1)
 Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=Sof(C14A)=Sof(H14D)=Sof(H14E)=
 Sof(H14F)=Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=1-FVAR(2)
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(2)
 Sof(C36A)=Sof(H36D)=Sof(H36E)=Sof(H36F)=Sof(C37A)=Sof(H37D)=Sof(H37E)=
 Sof(H37F)=Sof(C38A)=Sof(H38D)=Sof(H38E)=Sof(H38F)=1-FVAR(3)
 Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(H36C)=Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(H37C)=
 Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(H38C)=FVAR(3)
 Sof(C16A)=Sof(H16D)=Sof(H16E)=Sof(H16F)=Sof(C18A)=Sof(H18D)=Sof(H18E)=
 Sof(H18F)=Sof(C19A)=Sof(H19D)=Sof(H19E)=Sof(H19F)=1-FVAR(4)
 Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(H18C)=
 Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=FVAR(4)
5.a Me refined with riding coordinates:
 C32(H32A,H32B,H32C), C32A(H32D,H32E,H32F), C33(H33A,H33B,H33C), C33A(H33D,
 H33E,H33F), C34(H34A,H34B,H34C), C34A(H34D,H34E,H34F), C36(H36A,H36B,H36C),
 C36A(H36D,H36E,H36F), C37(H37A,H37B,H37C), C37A(H37D,H37E,H37F), C38(H38A,H38B,
 H38C), C38A(H38D,H38E,H38F)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C22(H22),
 C23(H23), C25(H25), C26(H26), C27(H27), C28(H28), C30(H30)
5.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C13A(H13D,H13E,H13F), C14(H14A,H14B,H14C), C14A(H14D,
 H14E,H14F), C15(H15A,H15B,H15C), C15A(H15D,H15E,H15F), C16(H16A,H16B,H16C),
 C16A(H16D,H16E,H16F), C18(H18A,H18B,H18C), C18A(H18D,H18E,H18F), C19(H19A,H19B,
 H19C), C19A(H19D,H19E,H19F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.7817(6) 0.6007(2) 0.55539(13) 0.183(2) Uani 1 1 d . . . . .
F2 F 0.8285(4) 0.50702(17) 0.55747(9) 0.1110(13) Uani 1 1 d . . . . .
N1 N 0.8630(5) 0.5623(2) 0.61352(11) 0.0874(16) Uani 1 1 d . . . . .
N2 N 1.0261(5) 0.5740(2) 0.57733(10) 0.0844(15) Uani 1 1 d . . . . .
C1 C 1.0020(6) 0.5752(2) 0.61192(11) 0.0587(13) Uani 1 1 d . . . . .
C2 C 1.1080(6) 0.5876(2) 0.64138(11) 0.0607(13) Uani 1 1 d . . . . .
C3 C 1.1686(5) 0.5429(3) 0.66055(12) 0.0666(14) Uani 1 1 d . . . . .
H3 H 1.142953 0.503501 0.655026 0.080 Uiso 1 1 calc R U . . .
C4 C 1.2713(6) 0.5549(3) 0.68915(12) 0.0712(15) Uani 1 1 d . . . . .
C5 C 1.3358(7) 0.5089(3) 0.70877(14) 0.099(2) Uani 1 1 d . . . . .
H5 H 1.310642 0.469131 0.704109 0.118 Uiso 1 1 calc R U . . .
C6 C 1.4357(9) 0.5232(5) 0.73475(18) 0.131(3) Uani 1 1 d . . . . .
H6 H 1.483296 0.492722 0.747806 0.157 Uiso 1 1 calc R U . . .
C7 C 1.4700(8) 0.5822(5) 0.74266(18) 0.128(3) Uani 1 1 d . . . . .
H7 H 1.538652 0.590619 0.761301 0.153 Uiso 1 1 calc R U . . .
C8 C 1.4081(7) 0.6266(4) 0.72449(16) 0.110(3) Uani 1 1 d . . . . .
H8 H 1.431623 0.666199 0.730059 0.132 Uiso 1 1 calc R U . . .
C9 C 1.3063(6) 0.6129(3) 0.69669(13) 0.0763(16) Uani 1 1 d . . . . .
C10 C 1.2409(7) 0.6589(3) 0.67731(15) 0.0923(19) Uani 1 1 d . . . . .
H10 H 1.264771 0.698568 0.682719 0.111 Uiso 1 1 calc R U . . .
C11 C 1.1410(6) 0.6458(3) 0.65013(13) 0.0765(16) Uani 1 1 d . . . . .
H11 H 1.094588 0.676871 0.637315 0.092 Uiso 1 1 calc R U . . .
C12 C 1.1577(7) 0.5802(3) 0.55465(13) 0.0795(17) Uani 1 1 d D U . . .
C13 C 1.2440(14) 0.6333(4) 0.5649(3) 0.090(4) Uani 0.664(9) 1 d D U P A 1
H13A H 1.180643 0.668084 0.563628 0.135 Uiso 0.664(9) 1 calc R U P A 1
H13B H 1.326742 0.638065 0.548199 0.135 Uiso 0.664(9) 1 calc R U P A 1
H13C H 1.281263 0.628788 0.589573 0.135 Uiso 0.664(9) 1 calc R U P A 1
C13A C 1.196(3) 0.6403(7) 0.5459(7) 0.106(7) Uani 0.336(9) 1 d D U P A 2
H13D H 1.119122 0.657582 0.530837 0.159 Uiso 0.336(9) 1 calc R U P A 2
H13E H 1.289742 0.640874 0.532812 0.159 Uiso 0.336(9) 1 calc R U P A 2
H13F H 1.205913 0.663039 0.568291 0.159 Uiso 0.336(9) 1 calc R U P A 2
C14 C 1.0909(11) 0.5946(5) 0.51558(19) 0.097(3) Uani 0.664(9) 1 d D U P A 1
H14A H 1.017034 0.564962 0.509312 0.145 Uiso 0.664(9) 1 calc R U P A 1
H14B H 1.169863 0.594018 0.497565 0.145 Uiso 0.664(9) 1 calc R U P A 1
H14C H 1.045097 0.633506 0.515959 0.145 Uiso 0.664(9) 1 calc R U P A 1
C14A C 1.155(2) 0.5352(8) 0.5217(4) 0.093(6) Uani 0.336(9) 1 d D U P A 2
H14D H 1.157311 0.494876 0.530913 0.139 Uiso 0.336(9) 1 calc R U P A 2
H14E H 1.240695 0.541947 0.506199 0.139 Uiso 0.336(9) 1 calc R U P A 2
H14F H 1.064945 0.541091 0.507556 0.139 Uiso 0.336(9) 1 calc R U P A 2
C15 C 1.2351(15) 0.5244(4) 0.5560(3) 0.117(4) Uani 0.664(9) 1 d D U P A 1
H15A H 1.277515 0.518833 0.580072 0.176 Uiso 0.664(9) 1 calc R U P A 1
H15B H 1.313841 0.524243 0.537899 0.176 Uiso 0.664(9) 1 calc R U P A 1
H15C H 1.166219 0.492351 0.550828 0.176 Uiso 0.664(9) 1 calc R U P A 1
C15A C 1.301(2) 0.5566(11) 0.5733(5) 0.108(6) Uani 0.336(9) 1 d D U P A 2
H15D H 1.326063 0.581778 0.593816 0.163 Uiso 0.336(9) 1 calc R U P A 2
H15E H 1.381997 0.556833 0.555805 0.163 Uiso 0.336(9) 1 calc R U P A 2
H15F H 1.284462 0.516349 0.581771 0.163 Uiso 0.336(9) 1 calc R U P A 2
C16 C 0.6075(11) 0.5579(9) 0.6250(4) 0.135(5) Uani 0.704(16) 1 d D U P B 1
H16A H 0.588278 0.595404 0.612944 0.202 Uiso 0.704(16) 1 calc R U P B 1
H16B H 0.531696 0.550794 0.643324 0.202 Uiso 0.704(16) 1 calc R U P B 1
H16C H 0.605892 0.526093 0.607189 0.202 Uiso 0.704(16) 1 calc R U P B 1
C16A C 0.630(3) 0.5170(13) 0.6326(7) 0.098(7) Uani 0.296(16) 1 d D U P B 2
H16D H 0.601560 0.523753 0.607369 0.146 Uiso 0.296(16) 1 calc R U P B 2
H16E H 0.544727 0.524287 0.648284 0.146 Uiso 0.296(16) 1 calc R U P B 2
H16F H 0.662360 0.476311 0.635554 0.146 Uiso 0.296(16) 1 calc R U P B 2
C17 C 0.7583(7) 0.5600(3) 0.64319(15) 0.0824(17) Uani 1 1 d D U . . .
C18 C 0.7698(14) 0.6165(4) 0.6663(3) 0.090(3) Uani 0.704(16) 1 d D U P B 1
H18A H 0.868466 0.619277 0.676749 0.134 Uiso 0.704(16) 1 calc R U P B 1
H18B H 0.696780 0.615135 0.685746 0.134 Uiso 0.704(16) 1 calc R U P B 1
H18C H 0.751335 0.650894 0.651024 0.134 Uiso 0.704(16) 1 calc R U P B 1
C18A C 0.686(4) 0.6194(9) 0.6483(10) 0.119(7) Uani 0.296(16) 1 d D U P B 2
H18D H 0.641271 0.632009 0.625477 0.178 Uiso 0.296(16) 1 calc R U P B 2
H18E H 0.759623 0.648195 0.655866 0.178 Uiso 0.296(16) 1 calc R U P B 2
H18F H 0.609400 0.616356 0.666893 0.178 Uiso 0.296(16) 1 calc R U P B 2
C19 C 0.7908(16) 0.5068(5) 0.6661(4) 0.107(4) Uani 0.704(16) 1 d D U P B 1
H19A H 0.800000 0.472145 0.650510 0.161 Uiso 0.704(16) 1 calc R U P B 1
H19B H 0.710485 0.500687 0.683325 0.161 Uiso 0.704(16) 1 calc R U P B 1
H19C H 0.882881 0.512873 0.679260 0.161 Uiso 0.704(16) 1 calc R U P B 1
C19A C 0.806(4) 0.5328(15) 0.6784(6) 0.105(7) Uani 0.296(16) 1 d D U P B 2
H19D H 0.879894 0.502282 0.673556 0.158 Uiso 0.296(16) 1 calc R U P B 2
H19E H 0.721364 0.515240 0.690485 0.158 Uiso 0.296(16) 1 calc R U P B 2
H19F H 0.849417 0.563094 0.693906 0.158 Uiso 0.296(16) 1 calc R U P B 2
B1 B 0.8614(8) 0.5586(3) 0.57160(15) 0.0747(19) Uani 1 1 d . . . . .
F3 F -0.0576(5) 0.60759(19) 0.31186(11) 0.1270(14) Uani 1 1 d . . . . .
F4 F -0.0766(5) 0.7037(2) 0.30618(11) 0.1444(17) Uani 1 1 d . . . . .
N3 N -0.0030(5) 0.6668(3) 0.36642(11) 0.0968(18) Uani 1 1 d . . . . .
N4 N 0.1600(5) 0.6659(2) 0.32905(10) 0.0857(15) Uani 1 1 d . . . . .
C20 C 0.1387(6) 0.6721(2) 0.36430(12) 0.0617(13) Uani 1 1 d . . . . .
C21 C 0.2454(5) 0.6817(2) 0.39369(11) 0.0610(13) Uani 1 1 d . . . . .
C22 C 0.2783(7) 0.7402(3) 0.40424(14) 0.0805(17) Uani 1 1 d . . . . .
H22 H 0.235967 0.772269 0.391564 0.097 Uiso 1 1 calc R U . . .
C23 C 0.3701(7) 0.7503(3) 0.43236(15) 0.0823(17) Uani 1 1 d . . . . .
H23 H 0.391134 0.789505 0.439371 0.099 Uiso 1 1 calc R U . . .
C24 C 0.4342(6) 0.7037(2) 0.45117(13) 0.0632(13) Uani 1 1 d . . . . .
C25 C 0.5312(7) 0.7130(3) 0.48167(14) 0.0848(17) Uani 1 1 d . . . . .
H25 H 0.552293 0.751847 0.489498 0.102 Uiso 1 1 calc R U . . .
C26 C 0.5908(7) 0.6678(3) 0.49873(15) 0.0865(18) Uani 1 1 d . . . . .
H26 H 0.655465 0.674506 0.518438 0.104 Uiso 1 1 calc R U . . .
C27 C 0.5594(7) 0.6097(3) 0.48801(14) 0.0846(17) Uani 1 1 d . . . . .
H27 H 0.603536 0.577740 0.500408 0.101 Uiso 1 1 calc R U . . .
C28 C 0.4659(6) 0.5992(3) 0.45995(14) 0.0757(16) Uani 1 1 d . . . . .
H28 H 0.444245 0.559905 0.453228 0.091 Uiso 1 1 calc R U . . .
C29 C 0.4022(5) 0.6453(2) 0.44113(12) 0.0605(13) Uani 1 1 d . . . . .
C30 C 0.3041(5) 0.6357(2) 0.41161(11) 0.0608(13) Uani 1 1 d . . . . .
H30 H 0.280058 0.596772 0.404535 0.073 Uiso 1 1 calc R U . . .
C31 C 0.2857(7) 0.6729(3) 0.30510(14) 0.0862(18) Uani 1 1 d D U . . .
C32 C 0.3129(16) 0.7348(4) 0.2982(4) 0.142(5) Uani 0.731(8) 1 d D U P C 1
H32A H 0.397678 0.738940 0.282069 0.213 Uiso 0.731(8) 1 calc R U P C 1
H32B H 0.226168 0.752394 0.286826 0.213 Uiso 0.731(8) 1 calc R U P C 1
H32C H 0.333280 0.754932 0.321081 0.213 Uiso 0.731(8) 1 calc R U P C 1
C32A C 0.227(3) 0.7112(15) 0.2746(7) 0.129(7) Uani 0.269(8) 1 d D U P C 2
H32D H 0.305619 0.718250 0.256942 0.193 Uiso 0.269(8) 1 calc R U P C 2
H32E H 0.144970 0.691238 0.262698 0.193 Uiso 0.269(8) 1 calc R U P C 2
H32F H 0.193509 0.748815 0.284440 0.193 Uiso 0.269(8) 1 calc R U P C 2
C33 C 0.2534(12) 0.6374(5) 0.2713(2) 0.116(4) Uani 0.731(8) 1 d D U P C 1
H33A H 0.335915 0.641018 0.254401 0.175 Uiso 0.731(8) 1 calc R U P C 1
H33B H 0.239863 0.596044 0.277777 0.175 Uiso 0.731(8) 1 calc R U P C 1
H33C H 0.163762 0.652304 0.259839 0.175 Uiso 0.731(8) 1 calc R U P C 1
C33A C 0.344(4) 0.6159(10) 0.2939(10) 0.139(8) Uani 0.269(8) 1 d D U P C 2
H33D H 0.428181 0.621809 0.277808 0.209 Uiso 0.269(8) 1 calc R U P C 2
H33E H 0.375129 0.593685 0.315224 0.209 Uiso 0.269(8) 1 calc R U P C 2
H33F H 0.267354 0.593876 0.281060 0.209 Uiso 0.269(8) 1 calc R U P C 2
C34 C 0.4246(10) 0.6430(5) 0.3211(3) 0.114(4) Uani 0.731(8) 1 d D U P C 1
H34A H 0.507411 0.648331 0.304473 0.171 Uiso 0.731(8) 1 calc R U P C 1
H34B H 0.448235 0.660879 0.344450 0.171 Uiso 0.731(8) 1 calc R U P C 1
H34C H 0.405799 0.600969 0.324386 0.171 Uiso 0.731(8) 1 calc R U P C 1
C34A C 0.409(3) 0.7122(15) 0.3222(7) 0.127(7) Uani 0.269(8) 1 d D U P C 2
H34D H 0.491360 0.715704 0.305205 0.190 Uiso 0.269(8) 1 calc R U P C 2
H34E H 0.369570 0.751337 0.327394 0.190 Uiso 0.269(8) 1 calc R U P C 2
H34F H 0.443914 0.694165 0.344674 0.190 Uiso 0.269(8) 1 calc R U P C 2
C35 C -0.1060(6) 0.6666(3) 0.39664(15) 0.0883(18) Uani 1 1 d D U . . .
C36 C -0.0698(17) 0.7134(8) 0.4251(4) 0.116(5) Uani 0.510(12) 1 d D U P D 1
H36A H -0.074735 0.752485 0.414016 0.174 Uiso 0.510(12) 1 calc R U P D 1
H36B H -0.141052 0.711046 0.444900 0.174 Uiso 0.510(12) 1 calc R U P D 1
H36C H 0.029324 0.706685 0.434539 0.174 Uiso 0.510(12) 1 calc R U P D 1
C36A C -0.139(3) 0.7276(7) 0.4048(6) 0.139(6) Uani 0.490(12) 1 d D U P D 2
H36D H -0.207811 0.729470 0.425074 0.208 Uiso 0.490(12) 1 calc R U P D 2
H36E H -0.047676 0.748047 0.411340 0.208 Uiso 0.490(12) 1 calc R U P D 2
H36F H -0.182402 0.746368 0.383573 0.208 Uiso 0.490(12) 1 calc R U P D 2
C37 C -0.2554(14) 0.6873(10) 0.3817(4) 0.126(5) Uani 0.510(12) 1 d D U P D 1
H37A H -0.244979 0.726811 0.371494 0.189 Uiso 0.510(12) 1 calc R U P D 1
H37B H -0.288265 0.660169 0.362783 0.189 Uiso 0.510(12) 1 calc R U P D 1
H37C H -0.327840 0.688055 0.401260 0.189 Uiso 0.510(12) 1 calc R U P D 1
C37A C -0.2423(16) 0.6289(10) 0.3835(4) 0.132(6) Uani 0.490(12) 1 d D U P D 2
H37D H -0.210551 0.588586 0.378630 0.199 Uiso 0.490(12) 1 calc R U P D 2
H37E H -0.317783 0.628702 0.402408 0.199 Uiso 0.490(12) 1 calc R U P D 2
H37F H -0.282886 0.646228 0.361425 0.199 Uiso 0.490(12) 1 calc R U P D 2
C38 C -0.099(2) 0.6086(6) 0.4130(5) 0.125(6) Uani 0.510(12) 1 d D U P D 1
H38A H -0.166783 0.606724 0.433501 0.187 Uiso 0.510(12) 1 calc R U P D 1
H38B H -0.126321 0.578888 0.395066 0.187 Uiso 0.510(12) 1 calc R U P D 1
H38C H 0.001495 0.601059 0.421444 0.187 Uiso 0.510(12) 1 calc R U P D 1
C38A C -0.053(2) 0.6341(9) 0.4297(4) 0.109(5) Uani 0.490(12) 1 d D U P D 2
H38D H -0.031978 0.593157 0.423316 0.163 Uiso 0.490(12) 1 calc R U P D 2
H38E H 0.036520 0.652747 0.438882 0.163 Uiso 0.490(12) 1 calc R U P D 2
H38F H -0.129305 0.635184 0.448387 0.163 Uiso 0.490(12) 1 calc R U P D 2
B2 B -0.0104(9) 0.6596(4) 0.32429(17) 0.084(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.344(8) . ?
F2 B1 1.321(7) . ?
N1 C1 1.300(6) . ?
N1 C17 1.455(7) . ?
N1 B1 1.554(7) . ?
N2 C1 1.299(5) . ?
N2 C12 1.469(7) . ?
N2 B1 1.553(8) . ?
C1 C2 1.483(7) . ?
C2 C3 1.357(7) . ?
C2 C11 1.397(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.438(7) . ?
C4 C5 1.402(8) . ?
C4 C9 1.387(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.363(9) . ?
C6 H6 0.9500 . ?
C6 C7 1.410(11) . ?
C7 H7 0.9500 . ?
C7 C8 1.338(10) . ?
C8 H8 0.9500 . ?
C8 C9 1.419(8) . ?
C9 C10 1.402(8) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.491(10) . ?
C12 C13A 1.449(15) . ?
C12 C14 1.603(9) . ?
C12 C14A 1.594(13) . ?
C12 C15 1.454(10) . ?
C12 C15A 1.570(16) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13A H13D 0.9800 . ?
C13A H13E 0.9800 . ?
C13A H13F 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15A H15D 0.9800 . ?
C15A H15E 0.9800 . ?
C15A H15F 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 C17 1.529(11) . ?
C16A H16D 0.9800 . ?
C16A H16E 0.9800 . ?
C16A H16F 0.9800 . ?
C16A C17 1.576(16) . ?
C17 C18 1.548(10) . ?
C17 C18A 1.516(17) . ?
C17 C19 1.508(10) . ?
C17 C19A 1.507(16) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
F3 B2 1.342(8) . ?
F4 B2 1.349(8) . ?
N3 C20 1.297(6) . ?
N3 C35 1.459(7) . ?
N3 B2 1.569(7) . ?
N4 C20 1.326(5) . ?
N4 C31 1.456(7) . ?
N4 B2 1.567(9) . ?
C20 C21 1.475(7) . ?
C21 C22 1.419(7) . ?
C21 C30 1.350(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.354(7) . ?
C23 H23 0.9500 . ?
C23 C24 1.396(7) . ?
C24 C25 1.449(7) . ?
C24 C29 1.412(7) . ?
C25 H25 0.9500 . ?
C25 C26 1.324(8) . ?
C26 H26 0.9500 . ?
C26 C27 1.408(8) . ?
C27 H27 0.9500 . ?
C27 C28 1.364(7) . ?
C28 H28 0.9500 . ?
C28 C29 1.386(7) . ?
C29 C30 1.428(6) . ?
C30 H30 0.9500 . ?
C31 C32 1.455(10) . ?
C31 C32A 1.523(17) . ?
C31 C33 1.518(9) . ?
C31 C33A 1.462(18) . ?
C31 C34 1.553(10) . ?
C31 C34A 1.571(18) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C32A H32D 0.9800 . ?
C32A H32E 0.9800 . ?
C32A H32F 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C33A H33D 0.9800 . ?
C33A H33E 0.9800 . ?
C33A H33F 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C34A H34D 0.9800 . ?
C34A H34E 0.9800 . ?
C34A H34F 0.9800 . ?
C35 C36 1.534(13) . ?
C35 C36A 1.451(14) . ?
C35 C37 1.542(13) . ?
C35 C37A 1.585(14) . ?
C35 C38 1.455(13) . ?
C35 C38A 1.510(13) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C36A H36D 0.9800 . ?
C36A H36E 0.9800 . ?
C36A H36F 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C37A H37D 0.9800 . ?
C37A H37E 0.9800 . ?
C37A H37F 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C38A H38D 0.9800 . ?
C38A H38E 0.9800 . ?
C38A H38F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C17 132.8(4) . . ?
C1 N1 B1 88.6(4) . . ?
C17 N1 B1 138.2(5) . . ?
C1 N2 C12 134.3(5) . . ?
C1 N2 B1 88.6(4) . . ?
C12 N2 B1 136.9(4) . . ?
N1 C1 C2 130.0(4) . . ?
N2 C1 N1 101.8(4) . . ?
N2 C1 C2 128.2(5) . . ?
C3 C2 C1 120.3(5) . . ?
C3 C2 C11 120.2(5) . . ?
C11 C2 C1 119.4(5) . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.5(5) . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 120.8(6) . . ?
C9 C4 C3 118.5(5) . . ?
C9 C4 C5 120.7(6) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 C4 117.8(8) . . ?
C6 C5 H5 121.1 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.5(8) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.4(7) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 120.9 . . ?
C7 C8 C9 118.3(8) . . ?
C9 C8 H8 120.9 . . ?
C4 C9 C8 120.3(6) . . ?
C4 C9 C10 120.8(5) . . ?
C10 C9 C8 118.9(7) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.2(6) . . ?
C11 C10 H10 120.4 . . ?
C2 C11 H11 119.6 . . ?
C10 C11 C2 120.8(6) . . ?
C10 C11 H11 119.6 . . ?
N2 C12 C13 111.2(6) . . ?
N2 C12 C14 103.1(5) . . ?
N2 C12 C14A 111.3(8) . . ?
N2 C12 C15A 113.2(8) . . ?
C13 C12 C14 105.3(7) . . ?
C13A C12 N2 114.5(12) . . ?
C13A C12 C14A 116.1(13) . . ?
C13A C12 C15A 102.7(15) . . ?
C15 C12 N2 107.0(6) . . ?
C15 C12 C13 116.5(9) . . ?
C15 C12 C14 113.1(7) . . ?
C15A C12 C14A 97.4(12) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C13A H13D 109.5 . . ?
C12 C13A H13E 109.5 . . ?
C12 C13A H13F 109.5 . . ?
H13D C13A H13E 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C14A H14D 109.5 . . ?
C12 C14A H14E 109.5 . . ?
C12 C14A H14F 109.5 . . ?
H14D C14A H14E 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C15A H15D 109.5 . . ?
C12 C15A H15E 109.5 . . ?
C12 C15A H15F 109.5 . . ?
H15D C15A H15E 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
C17 C16A H16D 109.5 . . ?
C17 C16A H16E 109.5 . . ?
C17 C16A H16F 109.5 . . ?
N1 C17 C16 104.9(6) . . ?
N1 C17 C16A 108.7(11) . . ?
N1 C17 C18 110.1(6) . . ?
N1 C17 C18A 110.4(11) . . ?
N1 C17 C19 108.9(7) . . ?
N1 C17 C19A 118.4(14) . . ?
C16 C17 C18 109.3(8) . . ?
C18A C17 C16A 105.1(16) . . ?
C19 C17 C16 113.4(10) . . ?
C19 C17 C18 110.1(7) . . ?
C19A C17 C16A 100.1(16) . . ?
C19A C17 C18A 112.7(16) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C18A H18D 109.5 . . ?
C17 C18A H18E 109.5 . . ?
C17 C18A H18F 109.5 . . ?
H18D C18A H18E 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C19A H19D 109.5 . . ?
C17 C19A H19E 109.5 . . ?
C17 C19A H19F 109.5 . . ?
H19D C19A H19E 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
F1 B1 N1 114.4(6) . . ?
F1 B1 N2 114.9(6) . . ?
F2 B1 F1 109.6(5) . . ?
F2 B1 N1 116.4(5) . . ?
F2 B1 N2 118.2(6) . . ?
N1 B1 N2 81.0(4) . . ?
C20 N3 C35 133.2(5) . . ?
C20 N3 B2 89.6(4) . . ?
C35 N3 B2 137.2(5) . . ?
C20 N4 C31 134.6(5) . . ?
C20 N4 B2 88.6(4) . . ?
C31 N4 B2 136.0(4) . . ?
N3 C20 N4 101.2(4) . . ?
N3 C20 C21 128.6(4) . . ?
N4 C20 C21 130.2(5) . . ?
C22 C21 C20 118.8(5) . . ?
C30 C21 C20 120.5(5) . . ?
C30 C21 C22 120.6(5) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.1(5) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.6 . . ?
C22 C23 C24 120.8(5) . . ?
C24 C23 H23 119.6 . . ?
C23 C24 C25 122.2(5) . . ?
C23 C24 C29 119.9(5) . . ?
C29 C24 C25 117.9(5) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.5(6) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 H26 119.6 . . ?
C25 C26 C27 120.8(6) . . ?
C27 C26 H26 119.6 . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.4(6) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 H28 119.6 . . ?
C27 C28 C29 120.7(6) . . ?
C29 C28 H28 119.6 . . ?
C24 C29 C30 118.3(5) . . ?
C28 C29 C24 119.6(5) . . ?
C28 C29 C30 122.1(5) . . ?
C21 C30 C29 120.3(5) . . ?
C21 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
N4 C31 C32 110.3(7) . . ?
N4 C31 C32A 103.9(12) . . ?
N4 C31 C33 107.0(6) . . ?
N4 C31 C33A 111.1(13) . . ?
N4 C31 C34 111.1(5) . . ?
N4 C31 C34A 112.3(10) . . ?
C32 C31 C33 113.8(8) . . ?
C32 C31 C34 110.6(9) . . ?
C32A C31 C34A 102.8(19) . . ?
C33 C31 C34 103.8(7) . . ?
C33A C31 C32A 115.1(19) . . ?
C33A C31 C34A 111(2) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C32A H32D 109.5 . . ?
C31 C32A H32E 109.5 . . ?
C31 C32A H32F 109.5 . . ?
H32D C32A H32E 109.5 . . ?
H32D C32A H32F 109.5 . . ?
H32E C32A H32F 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 C33A H33D 109.5 . . ?
C31 C33A H33E 109.5 . . ?
C31 C33A H33F 109.5 . . ?
H33D C33A H33E 109.5 . . ?
H33D C33A H33F 109.5 . . ?
H33E C33A H33F 109.5 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C31 C34A H34D 109.5 . . ?
C31 C34A H34E 109.5 . . ?
C31 C34A H34F 109.5 . . ?
H34D C34A H34E 109.5 . . ?
H34D C34A H34F 109.5 . . ?
H34E C34A H34F 109.5 . . ?
N3 C35 C36 112.8(8) . . ?
N3 C35 C37 106.9(7) . . ?
N3 C35 C37A 105.6(7) . . ?
N3 C35 C38A 114.7(8) . . ?
C36 C35 C37 102.9(10) . . ?
C36A C35 N3 106.8(9) . . ?
C36A C35 C37A 114.9(12) . . ?
C36A C35 C38A 111.4(11) . . ?
C38 C35 N3 107.0(9) . . ?
C38 C35 C36 109.6(11) . . ?
C38 C35 C37 117.8(12) . . ?
C38A C35 C37A 103.4(11) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C36A H36D 109.5 . . ?
C35 C36A H36E 109.5 . . ?
C35 C36A H36F 109.5 . . ?
H36D C36A H36E 109.5 . . ?
H36D C36A H36F 109.5 . . ?
H36E C36A H36F 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C35 C37A H37D 109.5 . . ?
C35 C37A H37E 109.5 . . ?
C35 C37A H37F 109.5 . . ?
H37D C37A H37E 109.5 . . ?
H37D C37A H37F 109.5 . . ?
H37E C37A H37F 109.5 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C35 C38A H38D 109.5 . . ?
C35 C38A H38E 109.5 . . ?
C35 C38A H38F 109.5 . . ?
H38D C38A H38E 109.5 . . ?
H38D C38A H38F 109.5 . . ?
H38E C38A H38F 109.5 . . ?
F3 B2 F4 110.1(6) . . ?
F3 B2 N3 116.5(6) . . ?
F3 B2 N4 115.8(6) . . ?
F4 B2 N3 115.8(6) . . ?
F4 B2 N4 115.5(6) . . ?
N4 B2 N3 80.6(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 79.3(7) . . . . ?
N1 C1 C2 C11 -98.4(7) . . . . ?
N2 C1 C2 C3 -100.1(7) . . . . ?
N2 C1 C2 C11 82.2(7) . . . . ?
C1 N1 C17 C16 165.4(10) . . . . ?
C1 N1 C17 C16A -155.9(15) . . . . ?
C1 N1 C17 C18 47.9(10) . . . . ?
C1 N1 C17 C18A 89.3(19) . . . . ?
C1 N1 C17 C19 -72.9(10) . . . . ?
C1 N1 C17 C19A -43(2) . . . . ?
C1 N1 B1 F1 -112.9(6) . . . . ?
C1 N1 B1 F2 117.6(6) . . . . ?
C1 N1 B1 N2 0.5(4) . . . . ?
C1 N2 C12 C13 -49.7(10) . . . . ?
C1 N2 C12 C13A -85.7(15) . . . . ?
C1 N2 C12 C14 -162.1(7) . . . . ?
C1 N2 C12 C14A 140.2(11) . . . . ?
C1 N2 C12 C15 78.4(10) . . . . ?
C1 N2 C12 C15A 31.6(14) . . . . ?
C1 N2 B1 F1 112.3(6) . . . . ?
C1 N2 B1 F2 -115.7(5) . . . . ?
C1 N2 B1 N1 -0.5(4) . . . . ?
C1 C2 C3 C4 -179.9(4) . . . . ?
C1 C2 C11 C10 -179.3(5) . . . . ?
C2 C3 C4 C5 -179.2(5) . . . . ?
C2 C3 C4 C9 0.2(7) . . . . ?
C3 C2 C11 C10 3.0(8) . . . . ?
C3 C4 C5 C6 177.9(5) . . . . ?
C3 C4 C9 C8 -179.5(5) . . . . ?
C3 C4 C9 C10 1.2(7) . . . . ?
C4 C5 C6 C7 2.1(10) . . . . ?
C4 C9 C10 C11 -0.5(8) . . . . ?
C5 C4 C9 C8 -0.1(8) . . . . ?
C5 C4 C9 C10 -179.4(5) . . . . ?
C5 C6 C7 C8 -1.4(12) . . . . ?
C6 C7 C8 C9 -0.2(11) . . . . ?
C7 C8 C9 C4 0.9(9) . . . . ?
C7 C8 C9 C10 -179.7(6) . . . . ?
C8 C9 C10 C11 -179.9(5) . . . . ?
C9 C4 C5 C6 -1.4(8) . . . . ?
C9 C10 C11 C2 -1.6(8) . . . . ?
C11 C2 C3 C4 -2.2(7) . . . . ?
C12 N2 C1 N1 -175.3(6) . . . . ?
C12 N2 C1 C2 4.2(10) . . . . ?
C12 N2 B1 F1 -72.0(9) . . . . ?
C12 N2 B1 F2 60.0(10) . . . . ?
C12 N2 B1 N1 175.2(7) . . . . ?
C17 N1 C1 N2 -174.5(6) . . . . ?
C17 N1 C1 C2 6.0(11) . . . . ?
C17 N1 B1 F1 60.4(10) . . . . ?
C17 N1 B1 F2 -69.1(10) . . . . ?
C17 N1 B1 N2 173.8(7) . . . . ?
B1 N1 C1 N2 -0.6(5) . . . . ?
B1 N1 C1 C2 179.9(6) . . . . ?
B1 N1 C17 C16 -5.5(13) . . . . ?
B1 N1 C17 C16A 33.3(17) . . . . ?
B1 N1 C17 C18 -122.9(9) . . . . ?
B1 N1 C17 C18A -82(2) . . . . ?
B1 N1 C17 C19 116.2(10) . . . . ?
B1 N1 C17 C19A 146.4(18) . . . . ?
B1 N2 C1 N1 0.6(5) . . . . ?
B1 N2 C1 C2 -179.9(5) . . . . ?
B1 N2 C12 C13 136.3(8) . . . . ?
B1 N2 C12 C13A 100.4(15) . . . . ?
B1 N2 C12 C14 24.0(10) . . . . ?
B1 N2 C12 C14A -33.7(13) . . . . ?
B1 N2 C12 C15 -95.5(10) . . . . ?
B1 N2 C12 C15A -142.3(12) . . . . ?
N3 C20 C21 C22 -88.4(7) . . . . ?
N3 C20 C21 C30 87.9(7) . . . . ?
N4 C20 C21 C22 92.4(7) . . . . ?
N4 C20 C21 C30 -91.3(7) . . . . ?
C20 N3 C35 C36 41.7(14) . . . . ?
C20 N3 C35 C36A 84.1(14) . . . . ?
C20 N3 C35 C37 154.1(12) . . . . ?
C20 N3 C35 C37A -153.1(11) . . . . ?
C20 N3 C35 C38 -78.9(13) . . . . ?
C20 N3 C35 C38A -39.9(15) . . . . ?
C20 N3 B2 F3 115.3(7) . . . . ?
C20 N3 B2 F4 -112.7(7) . . . . ?
C20 N3 B2 N4 1.1(5) . . . . ?
C20 N4 C31 C32 -77.1(11) . . . . ?
C20 N4 C31 C32A -130.5(17) . . . . ?
C20 N4 C31 C33 158.6(8) . . . . ?
C20 N4 C31 C33A 105(2) . . . . ?
C20 N4 C31 C34 45.9(11) . . . . ?
C20 N4 C31 C34A -20.1(19) . . . . ?
C20 N4 B2 F3 -116.0(6) . . . . ?
C20 N4 B2 F4 113.2(6) . . . . ?
C20 N4 B2 N3 -1.1(5) . . . . ?
C20 C21 C22 C23 176.6(5) . . . . ?
C20 C21 C30 C29 -177.1(4) . . . . ?
C21 C22 C23 C24 0.4(9) . . . . ?
C22 C21 C30 C29 -1.0(7) . . . . ?
C22 C23 C24 C25 -179.1(5) . . . . ?
C22 C23 C24 C29 -0.7(8) . . . . ?
C23 C24 C25 C26 -179.6(6) . . . . ?
C23 C24 C29 C28 -179.8(5) . . . . ?
C23 C24 C29 C30 0.1(7) . . . . ?
C24 C25 C26 C27 -1.0(9) . . . . ?
C24 C29 C30 C21 0.7(7) . . . . ?
C25 C24 C29 C28 -1.3(7) . . . . ?
C25 C24 C29 C30 178.6(4) . . . . ?
C25 C26 C27 C28 -0.5(9) . . . . ?
C26 C27 C28 C29 1.1(9) . . . . ?
C27 C28 C29 C24 -0.1(8) . . . . ?
C27 C28 C29 C30 179.9(5) . . . . ?
C28 C29 C30 C21 -179.3(5) . . . . ?
C29 C24 C25 C26 1.9(8) . . . . ?
C30 C21 C22 C23 0.4(8) . . . . ?
C31 N4 C20 N3 171.7(7) . . . . ?
C31 N4 C20 C21 -8.9(11) . . . . ?
C31 N4 B2 F3 73.8(10) . . . . ?
C31 N4 B2 F4 -57.0(10) . . . . ?
C31 N4 B2 N3 -171.2(7) . . . . ?
C35 N3 C20 N4 177.6(7) . . . . ?
C35 N3 C20 C21 -1.8(12) . . . . ?
C35 N3 B2 F3 -63.5(11) . . . . ?
C35 N3 B2 F4 68.5(11) . . . . ?
C35 N3 B2 N4 -177.7(8) . . . . ?
B2 N3 C20 N4 -1.3(6) . . . . ?
B2 N3 C20 C21 179.3(6) . . . . ?
B2 N3 C35 C36 -139.9(11) . . . . ?
B2 N3 C35 C36A -97.5(14) . . . . ?
B2 N3 C35 C37 -27.5(14) . . . . ?
B2 N3 C35 C37A 25.3(14) . . . . ?
B2 N3 C35 C38 99.5(13) . . . . ?
B2 N3 C35 C38A 138.5(12) . . . . ?
B2 N4 C20 N3 1.3(6) . . . . ?
B2 N4 C20 C21 -179.3(6) . . . . ?
B2 N4 C31 C32 89.0(11) . . . . ?
B2 N4 C31 C32A 35.5(18) . . . . ?
B2 N4 C31 C33 -35.3(11) . . . . ?
B2 N4 C31 C33A -89(2) . . . . ?
B2 N4 C31 C34 -148.0(8) . . . . ?
B2 N4 C31 C34A 145.9(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
