# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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. 
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#######################################################################

data_02825JorgeLabella
_database_code_depnum_ccdc_archive 'CCDC 1985328'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles'
;Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            JL-376-1_250K
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H29 B F2 N2 O0.50'
_chemical_formula_iupac          ?
_chemical_formula_weight         546.42

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   24.3250(9)
_cell_length_b                   9.9336(4)
_cell_length_c                   28.2901(12)
_cell_angle_alpha                90
_cell_angle_beta                 104.9532(14)
_cell_angle_gamma                90
_cell_volume                     6604.4(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5428
_cell_measurement_theta_min      2.2258
_cell_measurement_theta_max      19.9060
_cell_measurement_temperature    250.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'intense purple'
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.059
_exptl_crystal_size_min          0.052
_exptl_crystal_density_diffrn    1.099
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2288

_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.7004
_exptl_absorpt_correction_T_max  0.7454

_exptl_special_details           
;
;

_diffrn_ambient_temperature      250.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            56003
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       34

_refine_special_details          
;
;

_reflns_number_total             6031
_reflns_number_gt                3439
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1390
_refine_ls_R_factor_gt           0.0746
_refine_ls_wR_factor_gt          0.2262
_refine_ls_wR_factor_ref         0.2774
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_number_reflns         6031
_refine_ls_number_parameters     387
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1767P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.066
_refine_diff_density_min         -0.424
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.28112(16) 0.7253(4) 0.42720(14) 0.0453(9) Uani d . . . 1 . .
C C1 0.30096(13) 0.8469(3) 0.35290(12) 0.0471(8) Uani d . . . 1 . .
H H1 0.2725 0.9126 0.3503 0.057 Uiso calc U . R 1 . .
C C2 0.33860(13) 0.8424(3) 0.32349(11) 0.0441(8) Uani d . . . 1 . .
C C3 0.37353(13) 0.7307(3) 0.33989(11) 0.0445(8) Uani d . . . 1 . .
H H3 0.4037 0.701 0.3274 0.053 Uiso calc U . R 1 . .
C C4 0.35560(12) 0.6715(3) 0.37810(11) 0.0409(7) Uani d . . . 1 . .
C C5 0.37473(12) 0.5569(3) 0.40650(11) 0.0411(8) Uani d . . . 1 . .
C C6 0.34821(12) 0.5158(3) 0.44187(11) 0.0417(8) Uani d . . . 1 . .
C C7 0.35788(13) 0.4045(3) 0.47360(12) 0.0458(8) Uani d . . . 1 . .
H H7 0.3856 0.3377 0.4751 0.055 Uiso calc U . R 1 . .
C C8 0.31982(13) 0.4097(3) 0.50215(12) 0.0450(8) Uani d . . . 1 . .
C C9 0.28678(13) 0.5290(3) 0.48674(12) 0.0469(8) Uani d . . . 1 . .
H H9 0.2576 0.5598 0.5002 0.056 Uiso calc U . R 1 . .
C C10 0.33868(14) 0.9368(3) 0.28344(11) 0.0474(8) Uani d . . . 1 . .
C C11 0.28713(17) 0.9905(4) 0.25675(13) 0.0639(10) Uani d . . . 1 . .
H H11 0.2533 0.9635 0.2642 0.077 Uiso calc U . R 1 . .
C C12 0.2844(2) 1.0822(4) 0.21957(15) 0.0769(12) Uani d . . . 1 . .
H H12 0.249 1.1172 0.2022 0.092 Uiso calc U . R 1 . .
C C13 0.3327(2) 1.1218(4) 0.20812(15) 0.0795(13) Uani d . . . 1 . .
H H13 0.3308 1.1838 0.1826 0.095 Uiso calc U . R 1 . .
C C14 0.3839(2) 1.0720(4) 0.23345(15) 0.0741(12) Uani d . . . 1 . .
H H14 0.4171 1.1002 0.2252 0.089 Uiso calc U . R 1 . .
C C15 0.38815(15) 0.9789(4) 0.27177(13) 0.0561(9) Uani d . . . 1 . .
C C16 0.4423(2) 0.9347(4) 0.29810(16) 0.0710(11) Uani d . . . 1 . .
C C17 0.4885(2) 0.8977(5) 0.3199(2) 0.0905(15) Uani d . . . 1 . .
C C18 0.5443(2) 0.8491(8) 0.3479(3) 0.147(3) Uani d . . . 1 . .
H H18A 0.5501 0.8733 0.3821 0.221 Uiso calc U . R 1 . .
H H18B 0.5739 0.8899 0.3353 0.221 Uiso calc U . R 1 . .
H H18C 0.546 0.752 0.345 0.221 Uiso calc U . R 1 . .
C C19 0.31157(14) 0.3229(3) 0.54154(13) 0.0513(9) Uani d . . . 1 . .
C C20 0.28228(17) 0.3715(4) 0.57421(15) 0.0682(11) Uani d . . . 1 . .
H H20 0.2689 0.4606 0.5707 0.082 Uiso calc U . R 1 . .
C C21 0.27223(19) 0.2945(5) 0.61128(16) 0.0808(13) Uani d . . . 1 . .
H H21 0.2522 0.3313 0.6326 0.097 Uiso calc U . R 1 . .
C C22 0.29120(19) 0.1641(5) 0.61744(18) 0.0812(13) Uani d . . . 1 . .
H H22 0.2845 0.1112 0.6429 0.097 Uiso calc U . R 1 . .
C C23 0.31976(17) 0.1122(4) 0.58627(17) 0.0729(12) Uani d . . . 1 . .
H H23 0.3322 0.0224 0.5903 0.087 Uiso calc U . R 1 . .
C C24 0.33130(15) 0.1889(4) 0.54797(14) 0.0569(10) Uani d . . . 1 . .
C C25 0.36099(17) 0.1271(4) 0.51667(16) 0.0650(11) Uani d . . . 1 . .
C C26 0.38644(19) 0.0708(4) 0.49147(18) 0.0760(13) Uani d . . . 1 . .
C C27 0.4160(2) 0.0061(6) 0.4584(2) 0.1121(18) Uani d . . . 1 . .
H H27A 0.3885 -0.0192 0.4283 0.168 Uiso calc U . R 1 . .
H H27B 0.4356 -0.0736 0.4739 0.168 Uiso calc U . R 1 . .
H H27C 0.4433 0.0684 0.451 0.168 Uiso calc U . R 1 . .
C C28 0.42563(13) 0.4795(3) 0.40048(12) 0.0456(8) Uani d . . . 1 . .
C C29 0.47973(14) 0.5305(4) 0.42245(13) 0.0581(10) Uani d . . . 1 . .
C C30 0.52673(16) 0.4540(5) 0.41963(17) 0.0780(13) Uani d . . . 1 . .
H H30 0.5634 0.4877 0.4339 0.094 Uiso calc U . R 1 . .
C C31 0.52132(19) 0.3298(5) 0.39652(19) 0.0828(13) Uani d . . . 1 . .
C C32 0.46761(19) 0.2852(4) 0.37458(17) 0.0778(13) Uani d . . . 1 . .
H H32 0.4635 0.2021 0.3581 0.093 Uiso calc U . R 1 . .
C C33 0.41863(15) 0.3574(4) 0.37546(15) 0.0603(10) Uani d . . . 1 . .
C C34 0.48824(17) 0.6617(5) 0.45014(17) 0.0799(13) Uani d . . . 1 . .
H H34A 0.4701 0.7339 0.4286 0.12 Uiso calc U . R 1 . .
H H34B 0.5286 0.6801 0.462 0.12 Uiso calc U . R 1 . .
H H34C 0.4715 0.6556 0.4777 0.12 Uiso calc U . R 1 . .
C C35 0.5739(2) 0.2472(7) 0.3961(3) 0.137(2) Uani d . . . 1 . .
H H35A 0.6074 0.3041 0.4051 0.206 Uiso calc U . R 1 . .
H H35B 0.5701 0.2111 0.3635 0.206 Uiso calc U . R 1 . .
H H35C 0.5777 0.1737 0.4193 0.206 Uiso calc U . R 1 . .
C C36 0.36158(19) 0.3049(5) 0.35040(19) 0.0878(14) Uani d . . . 1 . .
H H36A 0.3453 0.2597 0.374 0.132 Uiso calc U . R 1 . .
H H36B 0.365 0.2416 0.3252 0.132 Uiso calc U . R 1 . .
H H36C 0.3371 0.3789 0.3356 0.132 Uiso calc U . R 1 . .
F F1 0.29775(10) 0.82671(19) 0.46147(7) 0.0689(7) Uani d . . . 1 . .
F F2 0.22324(8) 0.7252(2) 0.40997(8) 0.0690(7) Uani d . . . 1 . .
N N1 0.31020(10) 0.7456(2) 0.38553(9) 0.0409(6) Uani d . . . 1 . .
N N2 0.30310(10) 0.5895(2) 0.45096(9) 0.0412(6) Uani d . . . 1 . .
O O1 0.1348(6) 0.0298(15) 0.2770(5) 0.103(4) Uiso d . P . 0.25 A 1
O O2 0.0797(17) 0.025(4) 0.2710(13) 0.139(12) Uiso d . P . 0.125 B 2
O O3 0.0319(13) 0.017(3) 0.2506(11) 0.112(9) Uiso d . P . 0.125 C 3


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 F2 . 1.366(4) ?
B1 F1 . 1.384(4) ?
B1 N1 . 1.537(5) ?
B1 N2 . 1.540(4) ?
C1 N1 . 1.345(4) ?
C1 C2 . 1.388(4) ?
C1 H1 . 0.94 ?
C2 C3 . 1.401(4) ?
C2 C10 . 1.472(5) ?
C3 C4 . 1.396(4) ?
C3 H3 . 0.94 ?
C4 N1 . 1.388(4) ?
C4 C5 . 1.402(4) ?
C5 C6 . 1.385(4) ?
C5 C28 . 1.504(4) ?
C6 N2 . 1.397(4) ?
C6 C7 . 1.405(4) ?
C7 C8 . 1.378(4) ?
C7 H7 . 0.94 ?
C8 C9 . 1.435(4) ?
C8 C19 . 1.463(5) ?
C9 N2 . 1.323(4) ?
C9 H9 . 0.94 ?
C10 C11 . 1.392(5) ?
C10 C15 . 1.392(5) ?
C11 C12 . 1.380(5) ?
C11 H11 . 0.94 ?
C12 C13 . 1.356(6) ?
C12 H12 . 0.94 ?
C13 C14 . 1.359(6) ?
C13 H13 . 0.94 ?
C14 C15 . 1.408(5) ?
C14 H14 . 0.94 ?
C15 C16 . 1.406(6) ?
C16 C17 . 1.192(6) ?
C17 C18 . 1.466(7) ?
C18 H18A . 0.97 ?
C18 H18B . 0.97 ?
C18 H18C . 0.97 ?
C19 C20 . 1.391(5) ?
C19 C24 . 1.410(5) ?
C20 C21 . 1.370(5) ?
C20 H20 . 0.94 ?
C21 C22 . 1.372(6) ?
C21 H21 . 0.94 ?
C22 C23 . 1.357(6) ?
C22 H22 . 0.94 ?
C23 C24 . 1.411(5) ?
C23 H23 . 0.94 ?
C24 C25 . 1.419(6) ?
C25 C26 . 1.197(6) ?
C26 C27 . 1.466(7) ?
C27 H27A . 0.97 ?
C27 H27B . 0.97 ?
C27 H27C . 0.97 ?
C28 C33 . 1.392(5) ?
C28 C29 . 1.397(5) ?
C29 C30 . 1.392(5) ?
C29 C34 . 1.507(6) ?
C30 C31 . 1.386(6) ?
C30 H30 . 0.94 ?
C31 C32 . 1.368(6) ?
C31 C35 . 1.522(6) ?
C32 C33 . 1.396(5) ?
C32 H32 . 0.94 ?
C33 C36 . 1.481(6) ?
C34 H34A . 0.97 ?
C34 H34B . 0.97 ?
C34 H34C . 0.97 ?
C35 H35A . 0.97 ?
C35 H35B . 0.97 ?
C35 H35C . 0.97 ?
C36 H36A . 0.97 ?
C36 H36B . 0.97 ?
C36 H36C . 0.97 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F2 B1 F1 . . 109.8(3) ?
F2 B1 N1 . . 111.2(3) ?
F1 B1 N1 . . 109.4(3) ?
F2 B1 N2 . . 111.4(3) ?
F1 B1 N2 . . 109.0(3) ?
N1 B1 N2 . . 105.9(2) ?
N1 C1 C2 . . 111.6(3) ?
N1 C1 H1 . . 124.2 ?
C2 C1 H1 . . 124.2 ?
C1 C2 C3 . . 105.4(3) ?
C1 C2 C10 . . 125.0(3) ?
C3 C2 C10 . . 129.7(3) ?
C4 C3 C2 . . 107.8(3) ?
C4 C3 H3 . . 126.1 ?
C2 C3 H3 . . 126.1 ?
N1 C4 C3 . . 108.3(3) ?
N1 C4 C5 . . 120.2(3) ?
C3 C4 C5 . . 131.5(3) ?
C6 C5 C4 . . 120.4(3) ?
C6 C5 C28 . . 118.8(3) ?
C4 C5 C28 . . 120.8(3) ?
C5 C6 N2 . . 120.9(3) ?
C5 C6 C7 . . 131.4(3) ?
N2 C6 C7 . . 107.7(3) ?
C8 C7 C6 . . 108.5(3) ?
C8 C7 H7 . . 125.7 ?
C6 C7 H7 . . 125.7 ?
C7 C8 C9 . . 105.1(3) ?
C7 C8 C19 . . 132.0(3) ?
C9 C8 C19 . . 122.8(3) ?
N2 C9 C8 . . 110.6(3) ?
N2 C9 H9 . . 124.7 ?
C8 C9 H9 . . 124.7 ?
C11 C10 C15 . . 118.0(3) ?
C11 C10 C2 . . 118.8(3) ?
C15 C10 C2 . . 123.2(3) ?
C12 C11 C10 . . 121.7(4) ?
C12 C11 H11 . . 119.1 ?
C10 C11 H11 . . 119.1 ?
C13 C12 C11 . . 119.9(4) ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C12 C13 C14 . . 120.0(4) ?
C12 C13 H13 . . 120.0 ?
C14 C13 H13 . . 120.0 ?
C13 C14 C15 . . 121.4(4) ?
C13 C14 H14 . . 119.3 ?
C15 C14 H14 . . 119.3 ?
C10 C15 C16 . . 122.0(3) ?
C10 C15 C14 . . 118.9(4) ?
C16 C15 C14 . . 119.1(4) ?
C17 C16 C15 . . 179.1(5) ?
C16 C17 C18 . . 177.8(5) ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C20 C19 C24 . . 117.2(3) ?
C20 C19 C8 . . 119.7(3) ?
C24 C19 C8 . . 123.0(3) ?
C21 C20 C19 . . 122.6(4) ?
C21 C20 H20 . . 118.7 ?
C19 C20 H20 . . 118.7 ?
C20 C21 C22 . . 120.2(4) ?
C20 C21 H21 . . 119.9 ?
C22 C21 H21 . . 119.9 ?
C23 C22 C21 . . 119.2(4) ?
C23 C22 H22 . . 120.4 ?
C21 C22 H22 . . 120.4 ?
C22 C23 C24 . . 122.0(4) ?
C22 C23 H23 . . 119.0 ?
C24 C23 H23 . . 119.0 ?
C19 C24 C23 . . 118.7(4) ?
C19 C24 C25 . . 122.6(3) ?
C23 C24 C25 . . 118.6(4) ?
C26 C25 C24 . . 177.5(4) ?
C25 C26 C27 . . 177.0(5) ?
C26 C27 H27A . . 109.5 ?
C26 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C26 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C33 C28 C29 . . 121.3(3) ?
C33 C28 C5 . . 120.4(3) ?
C29 C28 C5 . . 118.2(3) ?
C30 C29 C28 . . 118.0(4) ?
C30 C29 C34 . . 119.8(3) ?
C28 C29 C34 . . 122.1(3) ?
C31 C30 C29 . . 122.2(4) ?
C31 C30 H30 . . 118.9 ?
C29 C30 H30 . . 118.9 ?
C32 C31 C30 . . 117.7(3) ?
C32 C31 C35 . . 121.9(5) ?
C30 C31 C35 . . 120.4(5) ?
C31 C32 C33 . . 123.0(4) ?
C31 C32 H32 . . 118.5 ?
C33 C32 H32 . . 118.5 ?
C28 C33 C32 . . 117.6(4) ?
C28 C33 C36 . . 121.8(3) ?
C32 C33 C36 . . 120.6(4) ?
C29 C34 H34A . . 109.5 ?
C29 C34 H34B . . 109.5 ?
H34A C34 H34B . . 109.5 ?
C29 C34 H34C . . 109.5 ?
H34A C34 H34C . . 109.5 ?
H34B C34 H34C . . 109.5 ?
C31 C35 H35A . . 109.5 ?
C31 C35 H35B . . 109.5 ?
H35A C35 H35B . . 109.5 ?
C31 C35 H35C . . 109.5 ?
H35A C35 H35C . . 109.5 ?
H35B C35 H35C . . 109.5 ?
C33 C36 H36A . . 109.5 ?
C33 C36 H36B . . 109.5 ?
H36A C36 H36B . . 109.5 ?
C33 C36 H36C . . 109.5 ?
H36A C36 H36C . . 109.5 ?
H36B C36 H36C . . 109.5 ?
C1 N1 C4 . . 106.9(3) ?
C1 N1 B1 . . 126.6(3) ?
C4 N1 B1 . . 126.0(3) ?
C9 N2 C6 . . 107.9(3) ?
C9 N2 B1 . . 126.4(3) ?
C6 N2 B1 . . 125.4(3) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . -0.6(4) ?
N1 C1 C2 C10 . . . . 178.4(3) ?
C1 C2 C3 C4 . . . . 0.5(3) ?
C10 C2 C3 C4 . . . . -178.4(3) ?
C2 C3 C4 N1 . . . . -0.2(3) ?
C2 C3 C4 C5 . . . . 178.4(3) ?
N1 C4 C5 C6 . . . . 0.6(4) ?
C3 C4 C5 C6 . . . . -177.9(3) ?
N1 C4 C5 C28 . . . . -177.1(3) ?
C3 C4 C5 C28 . . . . 4.4(5) ?
C4 C5 C6 N2 . . . . -1.9(4) ?
C28 C5 C6 N2 . . . . 175.9(3) ?
C4 C5 C6 C7 . . . . 177.9(3) ?
C28 C5 C6 C7 . . . . -4.4(5) ?
C5 C6 C7 C8 . . . . 179.7(3) ?
N2 C6 C7 C8 . . . . -0.5(3) ?
C6 C7 C8 C9 . . . . -0.3(3) ?
C6 C7 C8 C19 . . . . -178.4(3) ?
C7 C8 C9 N2 . . . . 1.1(4) ?
C19 C8 C9 N2 . . . . 179.4(3) ?
C1 C2 C10 C11 . . . . -32.7(5) ?
C3 C2 C10 C11 . . . . 146.0(3) ?
C1 C2 C10 C15 . . . . 145.3(3) ?
C3 C2 C10 C15 . . . . -36.1(5) ?
C15 C10 C11 C12 . . . . 0.3(5) ?
C2 C10 C11 C12 . . . . 178.3(3) ?
C10 C11 C12 C13 . . . . 0.3(6) ?
C11 C12 C13 C14 . . . . -0.4(7) ?
C12 C13 C14 C15 . . . . 0.0(7) ?
C11 C10 C15 C16 . . . . 177.2(4) ?
C2 C10 C15 C16 . . . . -0.7(5) ?
C11 C10 C15 C14 . . . . -0.7(5) ?
C2 C10 C15 C14 . . . . -178.6(3) ?
C13 C14 C15 C10 . . . . 0.5(6) ?
C13 C14 C15 C16 . . . . -177.4(4) ?
C7 C8 C19 C20 . . . . 160.3(4) ?
C9 C8 C19 C20 . . . . -17.5(5) ?
C7 C8 C19 C24 . . . . -20.7(6) ?
C9 C8 C19 C24 . . . . 161.5(3) ?
C24 C19 C20 C21 . . . . -0.2(6) ?
C8 C19 C20 C21 . . . . 178.8(4) ?
C19 C20 C21 C22 . . . . 0.0(7) ?
C20 C21 C22 C23 . . . . -0.3(7) ?
C21 C22 C23 C24 . . . . 0.9(6) ?
C20 C19 C24 C23 . . . . 0.8(5) ?
C8 C19 C24 C23 . . . . -178.2(3) ?
C20 C19 C24 C25 . . . . 179.1(3) ?
C8 C19 C24 C25 . . . . 0.1(5) ?
C22 C23 C24 C19 . . . . -1.1(5) ?
C22 C23 C24 C25 . . . . -179.5(4) ?
C6 C5 C28 C33 . . . . 78.4(4) ?
C4 C5 C28 C33 . . . . -103.9(4) ?
C6 C5 C28 C29 . . . . -98.8(4) ?
C4 C5 C28 C29 . . . . 78.9(4) ?
C33 C28 C29 C30 . . . . -1.5(5) ?
C5 C28 C29 C30 . . . . 175.7(3) ?
C33 C28 C29 C34 . . . . -179.4(4) ?
C5 C28 C29 C34 . . . . -2.2(5) ?
C28 C29 C30 C31 . . . . -0.9(6) ?
C34 C29 C30 C31 . . . . 177.1(4) ?
C29 C30 C31 C32 . . . . 2.3(7) ?
C29 C30 C31 C35 . . . . -177.6(5) ?
C30 C31 C32 C33 . . . . -1.5(7) ?
C35 C31 C32 C33 . . . . 178.4(5) ?
C29 C28 C33 C32 . . . . 2.3(6) ?
C5 C28 C33 C32 . . . . -174.9(3) ?
C29 C28 C33 C36 . . . . -177.6(4) ?
C5 C28 C33 C36 . . . . 5.2(6) ?
C31 C32 C33 C28 . . . . -0.8(7) ?
C31 C32 C33 C36 . . . . 179.1(4) ?
C2 C1 N1 C4 . . . . 0.5(3) ?
C2 C1 N1 B1 . . . . 173.7(3) ?
C3 C4 N1 C1 . . . . -0.2(3) ?
C5 C4 N1 C1 . . . . -179.0(3) ?
C3 C4 N1 B1 . . . . -173.4(3) ?
C5 C4 N1 B1 . . . . 7.8(4) ?
F2 B1 N1 C1 . . . . 54.5(4) ?
F1 B1 N1 C1 . . . . -67.0(4) ?
N2 B1 N1 C1 . . . . 175.6(3) ?
F2 B1 N1 C4 . . . . -133.6(3) ?
F1 B1 N1 C4 . . . . 104.9(3) ?
N2 B1 N1 C4 . . . . -12.5(4) ?
C8 C9 N2 C6 . . . . -1.4(3) ?
C8 C9 N2 B1 . . . . -175.2(3) ?
C5 C6 N2 C9 . . . . -179.0(3) ?
C7 C6 N2 C9 . . . . 1.2(3) ?
C5 C6 N2 B1 . . . . -5.1(5) ?
C7 C6 N2 B1 . . . . 175.1(3) ?
F2 B1 N2 C9 . . . . -55.1(4) ?
F1 B1 N2 C9 . . . . 66.2(4) ?
N1 B1 N2 C9 . . . . -176.2(3) ?
F2 B1 N2 C6 . . . . 132.1(3) ?
F1 B1 N2 C6 . . . . -106.6(3) ?
N1 B1 N2 C6 . . . . 11.1(4) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C9 H9 F1 7_566 0.94 2.24 3.160(4) 166.5 ?


####################################################################### 
# 
# 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_02816JorgeLabella
_database_code_depnum_ccdc_archive 'CCDC 1985329'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles'
;Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            JL376-21_250K
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H25 B F2 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         510.37

_chemical_melting_point          ?

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

_cell_length_a                   11.6062(5)
_cell_length_b                   32.6033(10)
_cell_length_c                   7.6374(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.632(2)
_cell_angle_gamma                90
_cell_volume                     2738.53(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4604
_cell_measurement_theta_min      3.0797
_cell_measurement_theta_max      22.0493
_cell_measurement_temperature    250.(2)

_exptl_crystal_description       ribbon
_exptl_crystal_colour            'clear intense purple'
_exptl_crystal_size_max          0.539
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.019
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1064

_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      250.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            27427
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9

_refine_special_details          
;
;

_reflns_number_total             5008
_reflns_number_gt                3284
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_gt          0.1316
_refine_ls_wR_factor_ref         0.1607
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_number_reflns         5008
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0859P)²+0.2109P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.304
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.5551(2) 0.45449(7) 0.2716(4) 0.0399(6) Uani d . . . 1 . .
C C1 0.4552(2) 0.41922(6) -0.0450(3) 0.0402(6) Uani d . . . 1 . .
H H1 0.408 0.4418 -0.1026 0.048 Uiso calc U . R 1 . .
C C2 0.4546(2) 0.38085(6) -0.1293(3) 0.0388(5) Uani d . . . 1 . .
C C3 0.5369(2) 0.35703(7) 0.0014(3) 0.0411(6) Uani d . . . 1 . .
H H3 0.557 0.3297 -0.0145 0.049 Uiso calc U . R 1 . .
C C4 0.58547(19) 0.38049(6) 0.1616(3) 0.0358(5) Uani d . . . 1 . .
C C5 0.67210(19) 0.37081(6) 0.3299(3) 0.0348(5) Uani d . . . 1 . .
C C6 0.7043(2) 0.39915(6) 0.4718(3) 0.0361(5) Uani d . . . 1 . .
C C7 0.7897(2) 0.39711(6) 0.6488(3) 0.0399(6) Uani d . . . 1 . .
H H7 0.8397 0.3745 0.6991 0.048 Uiso calc U . R 1 . .
C C8 0.7879(2) 0.43410(6) 0.7370(3) 0.0387(6) Uani d . . . 1 . .
C C9 0.6995(2) 0.45802(6) 0.6086(3) 0.0403(6) Uani d . . . 1 . .
H H9 0.6782 0.4848 0.6315 0.048 Uiso calc U . R 1 . .
C C10 0.3818(2) 0.36950(7) -0.3177(3) 0.0430(6) Uani d . . . 1 . .
C C11 0.3784(2) 0.39442(8) -0.4668(4) 0.0525(7) Uani d . . . 1 . .
H H11 0.4217 0.4193 -0.4454 0.063 Uiso calc U . R 1 . .
C C12 0.3132(2) 0.38353(10) -0.6458(4) 0.0646(8) Uani d . . . 1 . .
H H12 0.3138 0.4006 -0.7445 0.077 Uiso calc U . R 1 . .
C C13 0.2475(3) 0.34778(11) -0.6797(5) 0.0749(10) Uani d . . . 1 . .
H H13 0.2024 0.3405 -0.8015 0.09 Uiso calc U . R 1 . .
C C14 0.2478(3) 0.32268(9) -0.5352(5) 0.0707(9) Uani d . . . 1 . .
H H14 0.2022 0.2983 -0.559 0.085 Uiso calc U . R 1 . .
C C15 0.3141(2) 0.33271(7) -0.3547(4) 0.0537(7) Uani d . . . 1 . .
C C16 0.3099(3) 0.30616(9) -0.2081(5) 0.0696(9) Uani d . . . 1 . .
C C17 0.3063(3) 0.28426(11) -0.0879(7) 0.1041(13) Uani d . . . 1 . .
H H17 0.3034 0.2667 0.0083 0.125 Uiso calc U . R 1 . .
C C18 0.8608(2) 0.44714(6) 0.9232(3) 0.0401(6) Uani d . . . 1 . .
C C19 0.8065(2) 0.46904(7) 1.0313(4) 0.0503(6) Uani d . . . 1 . .
H H19 0.7231 0.4752 0.9845 0.06 Uiso calc U . R 1 . .
C C20 0.8727(3) 0.48200(9) 1.2062(4) 0.0635(8) Uani d . . . 1 . .
H H20 0.834 0.4966 1.2777 0.076 Uiso calc U . R 1 . .
C C21 0.9943(3) 0.47376(9) 1.2764(4) 0.0661(8) Uani d . . . 1 . .
H H21 1.0391 0.4826 1.3958 0.079 Uiso calc U . R 1 . .
C C22 1.0507(3) 0.45252(8) 1.1720(4) 0.0590(7) Uani d . . . 1 . .
H H22 1.1346 0.4473 1.2199 0.071 Uiso calc U . R 1 . .
C C23 0.9856(2) 0.43864(7) 0.9967(4) 0.0467(6) Uani d . . . 1 . .
C C24 1.0494(2) 0.41655(8) 0.8939(4) 0.0625(8) Uani d . . . 1 . .
C C25 1.1049(3) 0.39853(12) 0.8155(5) 0.0997(13) Uani d . . . 1 . .
H H25 1.1496 0.384 0.7525 0.12 Uiso calc U . R 1 . .
C C26 0.73283(19) 0.32967(6) 0.3525(3) 0.0339(5) Uani d . . . 1 . .
C C27 0.6752(2) 0.29507(6) 0.3933(3) 0.0411(6) Uani d . . . 1 . .
C C28 0.7324(2) 0.25726(7) 0.4017(3) 0.0459(6) Uani d . . . 1 . .
H H28 0.6938 0.2337 0.4273 0.055 Uiso calc U . R 1 . .
C C29 0.8431(2) 0.25305(6) 0.3740(3) 0.0441(6) Uani d . . . 1 . .
C C30 0.8982(2) 0.28804(7) 0.3399(3) 0.0446(6) Uani d . . . 1 . .
H H30 0.975 0.2858 0.324 0.054 Uiso calc U . R 1 . .
C C31 0.8461(2) 0.32643(6) 0.3279(3) 0.0392(6) Uani d . . . 1 . .
C C32 0.5553(3) 0.29797(8) 0.4289(5) 0.0704(9) Uani d . . . 1 . .
H H32A 0.5583 0.3202 0.5146 0.106 Uiso calc U . R 1 . .
H H32B 0.5391 0.2724 0.4815 0.106 Uiso calc U . R 1 . .
H H32C 0.4911 0.3032 0.3135 0.106 Uiso calc U . R 1 . .
C C33 0.9008(3) 0.21140(7) 0.3763(4) 0.0685(9) Uani d . . . 1 . .
H H33A 0.8533 0.1908 0.4142 0.103 Uiso calc U . R 1 . .
H H33B 0.9828 0.2117 0.4626 0.103 Uiso calc U . R 1 . .
H H33C 0.9032 0.2049 0.2535 0.103 Uiso calc U . R 1 . .
C C34 0.9102(2) 0.36363(7) 0.2859(4) 0.0615(8) Uani d . . . 1 . .
H H34A 0.856 0.3781 0.1806 0.092 Uiso calc U . R 1 . .
H H34B 0.9822 0.355 0.2576 0.092 Uiso calc U . R 1 . .
H H34C 0.9335 0.3817 0.3924 0.092 Uiso calc U . R 1 . .
F F1 0.44791(12) 0.46490(4) 0.3025(2) 0.0571(4) Uani d . . . 1 . .
F F2 0.60045(13) 0.48872(4) 0.2102(2) 0.0563(4) Uani d . . . 1 . .
N N1 0.53207(16) 0.41923(5) 0.1283(3) 0.0367(5) Uani d . . . 1 . .
N N2 0.64976(16) 0.43790(5) 0.4504(3) 0.0367(5) Uani d . . . 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 F2 . 1.379(3) ?
B1 F1 . 1.380(3) ?
B1 N1 . 1.551(3) ?
B1 N2 . 1.551(3) ?
C1 N1 . 1.339(3) ?
C1 C2 . 1.406(3) ?
C1 H1 . 0.94 ?
C2 C3 . 1.379(3) ?
C2 C10 . 1.465(3) ?
C3 C4 . 1.400(3) ?
C3 H3 . 0.94 ?
C4 C5 . 1.392(3) ?
C4 N1 . 1.394(3) ?
C5 C6 . 1.382(3) ?
C5 C26 . 1.499(3) ?
C6 N2 . 1.399(2) ?
C6 C7 . 1.399(3) ?
C7 C8 . 1.385(3) ?
C7 H7 . 0.94 ?
C8 C9 . 1.407(3) ?
C8 C18 . 1.467(3) ?
C9 N2 . 1.334(3) ?
C9 H9 . 0.94 ?
C10 C11 . 1.390(3) ?
C10 C15 . 1.412(3) ?
C11 C12 . 1.380(4) ?
C11 H11 . 0.94 ?
C12 C13 . 1.372(4) ?
C12 H12 . 0.94 ?
C13 C14 . 1.373(5) ?
C13 H13 . 0.94 ?
C14 C15 . 1.386(4) ?
C14 H14 . 0.94 ?
C15 C16 . 1.428(5) ?
C16 C17 . 1.174(5) ?
C17 H17 . 0.94 ?
C18 C19 . 1.386(3) ?
C18 C23 . 1.403(3) ?
C19 C20 . 1.377(4) ?
C19 H19 . 0.94 ?
C20 C21 . 1.367(4) ?
C20 H20 . 0.94 ?
C21 C22 . 1.370(4) ?
C21 H21 . 0.94 ?
C22 C23 . 1.386(4) ?
C22 H22 . 0.94 ?
C23 C24 . 1.433(4) ?
C24 C25 . 1.169(4) ?
C25 H25 . 0.94 ?
C26 C31 . 1.389(3) ?
C26 C27 . 1.397(3) ?
C27 C28 . 1.392(3) ?
C27 C32 . 1.504(3) ?
C28 C29 . 1.374(3) ?
C28 H28 . 0.94 ?
C29 C30 . 1.373(3) ?
C29 C33 . 1.512(3) ?
C30 C31 . 1.381(3) ?
C30 H30 . 0.94 ?
C31 C34 . 1.510(3) ?
C32 H32A . 0.97 ?
C32 H32B . 0.97 ?
C32 H32C . 0.97 ?
C33 H33A . 0.97 ?
C33 H33B . 0.97 ?
C33 H33C . 0.97 ?
C34 H34A . 0.97 ?
C34 H34B . 0.97 ?
C34 H34C . 0.97 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F2 B1 F1 . . 108.81(18) ?
F2 B1 N1 . . 111.0(2) ?
F1 B1 N1 . . 110.0(2) ?
F2 B1 N2 . . 110.0(2) ?
F1 B1 N2 . . 111.0(2) ?
N1 B1 N2 . . 106.05(16) ?
N1 C1 C2 . . 110.92(19) ?
N1 C1 H1 . . 124.5 ?
C2 C1 H1 . . 124.5 ?
C3 C2 C1 . . 105.6(2) ?
C3 C2 C10 . . 128.1(2) ?
C1 C2 C10 . . 126.3(2) ?
C2 C3 C4 . . 108.49(19) ?
C2 C3 H3 . . 125.8 ?
C4 C3 H3 . . 125.8 ?
C5 C4 N1 . . 121.44(19) ?
C5 C4 C3 . . 130.83(19) ?
N1 C4 C3 . . 107.73(19) ?
C6 C5 C4 . . 120.48(18) ?
C6 C5 C26 . . 120.6(2) ?
C4 C5 C26 . . 118.91(19) ?
C5 C6 N2 . . 120.9(2) ?
C5 C6 C7 . . 131.01(19) ?
N2 C6 C7 . . 108.07(18) ?
C8 C7 C6 . . 108.20(19) ?
C8 C7 H7 . . 125.9 ?
C6 C7 H7 . . 125.9 ?
C7 C8 C9 . . 105.3(2) ?
C7 C8 C18 . . 129.1(2) ?
C9 C8 C18 . . 125.58(19) ?
N2 C9 C8 . . 111.54(18) ?
N2 C9 H9 . . 124.2 ?
C8 C9 H9 . . 124.2 ?
C11 C10 C15 . . 117.7(2) ?
C11 C10 C2 . . 120.9(2) ?
C15 C10 C2 . . 121.4(2) ?
C12 C11 C10 . . 121.6(3) ?
C12 C11 H11 . . 119.2 ?
C10 C11 H11 . . 119.2 ?
C13 C12 C11 . . 120.1(3) ?
C13 C12 H12 . . 119.9 ?
C11 C12 H12 . . 119.9 ?
C12 C13 C14 . . 119.7(3) ?
C12 C13 H13 . . 120.1 ?
C14 C13 H13 . . 120.1 ?
C13 C14 C15 . . 121.1(3) ?
C13 C14 H14 . . 119.4 ?
C15 C14 H14 . . 119.4 ?
C14 C15 C10 . . 119.7(3) ?
C14 C15 C16 . . 119.3(3) ?
C10 C15 C16 . . 120.9(3) ?
C17 C16 C15 . . 179.8(4) ?
C16 C17 H17 . . 180.0 ?
C19 C18 C23 . . 118.1(2) ?
C19 C18 C8 . . 119.7(2) ?
C23 C18 C8 . . 122.2(2) ?
C20 C19 C18 . . 121.1(2) ?
C20 C19 H19 . . 119.4 ?
C18 C19 H19 . . 119.4 ?
C21 C20 C19 . . 120.4(3) ?
C21 C20 H20 . . 119.8 ?
C19 C20 H20 . . 119.8 ?
C20 C21 C22 . . 119.8(3) ?
C20 C21 H21 . . 120.1 ?
C22 C21 H21 . . 120.1 ?
C21 C22 C23 . . 120.8(3) ?
C21 C22 H22 . . 119.6 ?
C23 C22 H22 . . 119.6 ?
C22 C23 C18 . . 119.7(2) ?
C22 C23 C24 . . 118.4(2) ?
C18 C23 C24 . . 121.8(2) ?
C25 C24 C23 . . 177.6(3) ?
C24 C25 H25 . . 180.0 ?
C31 C26 C27 . . 120.67(18) ?
C31 C26 C5 . . 118.85(18) ?
C27 C26 C5 . . 120.46(19) ?
C28 C27 C26 . . 118.0(2) ?
C28 C27 C32 . . 120.2(2) ?
C26 C27 C32 . . 121.8(2) ?
C29 C28 C27 . . 122.5(2) ?
C29 C28 H28 . . 118.8 ?
C27 C28 H28 . . 118.8 ?
C30 C29 C28 . . 117.5(2) ?
C30 C29 C33 . . 121.1(2) ?
C28 C29 C33 . . 121.4(2) ?
C29 C30 C31 . . 123.0(2) ?
C29 C30 H30 . . 118.5 ?
C31 C30 H30 . . 118.5 ?
C30 C31 C26 . . 118.3(2) ?
C30 C31 C34 . . 120.4(2) ?
C26 C31 C34 . . 121.28(19) ?
C27 C32 H32A . . 109.5 ?
C27 C32 H32B . . 109.5 ?
H32A C32 H32B . . 109.5 ?
C27 C32 H32C . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
C29 C33 H33A . . 109.5 ?
C29 C33 H33B . . 109.5 ?
H33A C33 H33B . . 109.5 ?
C29 C33 H33C . . 109.5 ?
H33A C33 H33C . . 109.5 ?
H33B C33 H33C . . 109.5 ?
C31 C34 H34A . . 109.5 ?
C31 C34 H34B . . 109.5 ?
H34A C34 H34B . . 109.5 ?
C31 C34 H34C . . 109.5 ?
H34A C34 H34C . . 109.5 ?
H34B C34 H34C . . 109.5 ?
C1 N1 C4 . . 107.27(18) ?
C1 N1 B1 . . 127.43(18) ?
C4 N1 B1 . . 125.24(19) ?
C9 N2 C6 . . 106.85(18) ?
C9 N2 B1 . . 127.30(17) ?
C6 N2 B1 . . 125.77(18) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . -0.7(3) ?
N1 C1 C2 C10 . . . . 180.0(2) ?
C1 C2 C3 C4 . . . . 0.4(3) ?
C10 C2 C3 C4 . . . . 179.7(2) ?
C2 C3 C4 C5 . . . . -179.2(2) ?
C2 C3 C4 N1 . . . . 0.0(3) ?
N1 C4 C5 C6 . . . . 2.4(3) ?
C3 C4 C5 C6 . . . . -178.5(2) ?
N1 C4 C5 C26 . . . . -175.59(19) ?
C3 C4 C5 C26 . . . . 3.5(4) ?
C4 C5 C6 N2 . . . . 0.7(3) ?
C26 C5 C6 N2 . . . . 178.70(19) ?
C4 C5 C6 C7 . . . . -178.1(2) ?
C26 C5 C6 C7 . . . . -0.1(4) ?
C5 C6 C7 C8 . . . . 179.3(2) ?
N2 C6 C7 C8 . . . . 0.3(2) ?
C6 C7 C8 C9 . . . . 0.1(3) ?
C6 C7 C8 C18 . . . . -179.6(2) ?
C7 C8 C9 N2 . . . . -0.5(3) ?
C18 C8 C9 N2 . . . . 179.2(2) ?
C3 C2 C10 C11 . . . . -130.3(3) ?
C1 C2 C10 C11 . . . . 48.9(3) ?
C3 C2 C10 C15 . . . . 48.8(3) ?
C1 C2 C10 C15 . . . . -132.0(2) ?
C15 C10 C11 C12 . . . . -1.1(3) ?
C2 C10 C11 C12 . . . . 178.0(2) ?
C10 C11 C12 C13 . . . . 1.3(4) ?
C11 C12 C13 C14 . . . . -0.6(4) ?
C12 C13 C14 C15 . . . . -0.4(4) ?
C13 C14 C15 C10 . . . . 0.6(4) ?
C13 C14 C15 C16 . . . . 178.7(3) ?
C11 C10 C15 C14 . . . . 0.1(3) ?
C2 C10 C15 C14 . . . . -179.0(2) ?
C11 C10 C15 C16 . . . . -178.0(2) ?
C2 C10 C15 C16 . . . . 2.9(3) ?
C7 C8 C18 C19 . . . . -138.7(3) ?
C9 C8 C18 C19 . . . . 41.7(3) ?
C7 C8 C18 C23 . . . . 42.1(4) ?
C9 C8 C18 C23 . . . . -137.5(2) ?
C23 C18 C19 C20 . . . . -0.3(4) ?
C8 C18 C19 C20 . . . . -179.5(2) ?
C18 C19 C20 C21 . . . . 0.6(4) ?
C19 C20 C21 C22 . . . . 0.1(5) ?
C20 C21 C22 C23 . . . . -1.0(5) ?
C21 C22 C23 C18 . . . . 1.3(4) ?
C21 C22 C23 C24 . . . . -179.9(3) ?
C19 C18 C23 C22 . . . . -0.7(3) ?
C8 C18 C23 C22 . . . . 178.5(2) ?
C19 C18 C23 C24 . . . . -179.3(2) ?
C8 C18 C23 C24 . . . . -0.2(4) ?
C6 C5 C26 C31 . . . . -80.9(3) ?
C4 C5 C26 C31 . . . . 97.1(3) ?
C6 C5 C26 C27 . . . . 100.5(3) ?
C4 C5 C26 C27 . . . . -81.5(3) ?
C31 C26 C27 C28 . . . . -2.3(3) ?
C5 C26 C27 C28 . . . . 176.2(2) ?
C31 C26 C27 C32 . . . . 177.2(2) ?
C5 C26 C27 C32 . . . . -4.3(4) ?
C26 C27 C28 C29 . . . . 0.9(4) ?
C32 C27 C28 C29 . . . . -178.7(2) ?
C27 C28 C29 C30 . . . . 1.1(4) ?
C27 C28 C29 C33 . . . . -177.5(2) ?
C28 C29 C30 C31 . . . . -1.7(4) ?
C33 C29 C30 C31 . . . . 176.8(2) ?
C29 C30 C31 C26 . . . . 0.3(4) ?
C29 C30 C31 C34 . . . . -178.6(2) ?
C27 C26 C31 C30 . . . . 1.8(3) ?
C5 C26 C31 C30 . . . . -176.8(2) ?
C27 C26 C31 C34 . . . . -179.3(2) ?
C5 C26 C31 C34 . . . . 2.2(3) ?
C2 C1 N1 C4 . . . . 0.7(2) ?
C2 C1 N1 B1 . . . . -176.7(2) ?
C5 C4 N1 C1 . . . . 178.86(19) ?
C3 C4 N1 C1 . . . . -0.4(2) ?
C5 C4 N1 B1 . . . . -3.7(3) ?
C3 C4 N1 B1 . . . . 177.1(2) ?
F2 B1 N1 C1 . . . . -62.0(3) ?
F1 B1 N1 C1 . . . . 58.4(3) ?
N2 B1 N1 C1 . . . . 178.55(19) ?
F2 B1 N1 C4 . . . . 121.0(2) ?
F1 B1 N1 C4 . . . . -118.6(2) ?
N2 B1 N1 C4 . . . . 1.6(3) ?
C8 C9 N2 C6 . . . . 0.7(3) ?
C8 C9 N2 B1 . . . . -176.1(2) ?
C5 C6 N2 C9 . . . . -179.7(2) ?
C7 C6 N2 C9 . . . . -0.6(2) ?
C5 C6 N2 B1 . . . . -2.9(3) ?
C7 C6 N2 B1 . . . . 176.2(2) ?
F2 B1 N2 C9 . . . . 57.8(3) ?
F1 B1 N2 C9 . . . . -62.7(3) ?
N1 B1 N2 C9 . . . . 177.8(2) ?
F2 B1 N2 C6 . . . . -118.4(2) ?
F1 B1 N2 C6 . . . . 121.1(2) ?
N1 B1 N2 C6 . . . . 1.6(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C1 H1 F2 3_665 0.94 2.40 3.240(2) 148.7 ?
C9 H9 F1 3_666 0.94 2.36 3.232(2) 154.8 ?


####################################################################### 
# 
# 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_02809JorgeLabella
_database_code_depnum_ccdc_archive 'CCDC 1985337'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles'
;Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            JL376_1_250K
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H33 B F2 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         638.53

_chemical_melting_point          ?

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

_cell_length_a                   12.5426(5)
_cell_length_b                   41.2031(15)
_cell_length_c                   13.9741(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.8809(10)
_cell_angle_gamma                90
_cell_volume                     6497.4(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9539
_cell_measurement_theta_min      2.6773
_cell_measurement_theta_max      24.4002
_cell_measurement_temperature    250.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'dark blue-purple'
_exptl_crystal_size_max          0.195
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2672

_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      250.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            131931
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_theta_min         0.99
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             11877
_reflns_number_gt                7903
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_gt          0.1442
_refine_ls_wR_factor_ref         0.1878
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_number_reflns         11877
_refine_ls_number_parameters     893
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1251P)²+0.0648P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.322
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.4471(2) 0.54223(6) 0.2375(2) 0.0396(6) Uani d . . . 1 . .
B B2 0.1851(2) 0.31397(6) 0.4779(2) 0.0449(6) Uani d . . . 1 . .
C C1 0.23664(19) 0.51445(5) 0.18701(17) 0.0381(5) Uani d . . . 1 . .
C C2 0.19121(19) 0.48174(5) 0.17043(16) 0.0374(5) Uani d . . . 1 . .
C C3 0.28399(18) 0.46212(5) 0.17772(17) 0.0379(5) Uani d . . . 1 . .
H H3 0.2808 0.4395 0.1682 0.045 Uiso calc U . R 1 . .
C C4 0.38302(19) 0.48173(5) 0.20164(17) 0.0369(5) Uani d . . . 1 . .
C C5 0.49528(18) 0.47217(5) 0.21578(16) 0.0358(5) Uani d . . . 1 . .
C C6 0.58780(19) 0.49476(5) 0.24652(16) 0.0371(5) Uani d . . . 1 . .
C C7 0.70612(19) 0.48880(5) 0.27246(17) 0.0394(5) Uani d . . . 1 . .
H H7 0.7393 0.4685 0.27 0.047 Uiso calc U . R 1 . .
C C8 0.76711(19) 0.51809(5) 0.30284(16) 0.0369(5) Uani d . . . 1 . .
C C9 0.67852(19) 0.54218(5) 0.28781(16) 0.0367(5) Uani d . . . 1 . .
C C10 0.1608(2) 0.54155(5) 0.17179(19) 0.0463(6) Uani d . . . 1 . .
C C11 0.0442(2) 0.53399(6) 0.13831(18) 0.0489(6) Uani d . . . 1 . .
H H11 -0.0088 0.5515 0.1233 0.059 Uiso calc U . R 1 . .
C C12 -0.0050(2) 0.50237(6) 0.12383(17) 0.0438(5) Uani d . . . 1 . .
C C13 -0.1287(2) 0.49848(7) 0.08960(19) 0.0545(6) Uani d . . . 1 . .
H H13 -0.1775 0.5169 0.0738 0.065 Uiso calc U . R 1 . .
C C14 -0.1771(2) 0.46875(7) 0.0794(2) 0.0602(7) Uani d . . . 1 . .
H H14 -0.2598 0.4666 0.052 0.072 Uiso calc U . R 1 . .
C C15 -0.1049(2) 0.44060(7) 0.10960(19) 0.0526(6) Uani d . . . 1 . .
C C16 -0.1549(3) 0.40993(8) 0.1105(3) 0.0761(9) Uani d . . . 1 . .
H H16 -0.2374 0.408 0.0853 0.091 Uiso calc U . R 1 . .
C C17 -0.0850(3) 0.38305(8) 0.1474(3) 0.0815(9) Uani d . . . 1 . .
H H17 -0.1196 0.3628 0.147 0.098 Uiso calc U . R 1 . .
C C18 0.0377(3) 0.38564(7) 0.1857(2) 0.0670(8) Uani d . . . 1 . .
H H18 0.0858 0.3672 0.2129 0.08 Uiso calc U . R 1 . .
C C19 0.0880(2) 0.41487(6) 0.1837(2) 0.0536(6) Uani d . . . 1 . .
H H19 0.1707 0.4161 0.2089 0.064 Uiso calc U . R 1 . .
C C20 0.0195(2) 0.44338(6) 0.14470(17) 0.0445(6) Uani d . . . 1 . .
C C21 0.06880(19) 0.47510(5) 0.14616(16) 0.0386(5) Uani d . . . 1 . .
C C22 0.1984(2) 0.57654(6) 0.1868(3) 0.0667(8) Uani d . . . 1 . .
H H22A 0.2274 0.5824 0.1352 0.1 Uiso calc U . R 1 . .
H H22B 0.2609 0.5796 0.2581 0.1 Uiso calc U . R 1 . .
H H22C 0.1312 0.5901 0.1769 0.1 Uiso calc U . R 1 . .
C C23 0.7063(2) 0.57607(5) 0.29890(17) 0.0424(5) Uani d . . . 1 . .
C C24 0.8228(2) 0.58314(6) 0.32843(18) 0.0480(6) Uani d . . . 1 . .
H H24 0.8439 0.6052 0.3356 0.058 Uiso calc U . R 1 . .
C C25 0.9150(2) 0.56028(6) 0.34938(17) 0.0452(6) Uani d . . . 1 . .
C C26 1.0327(2) 0.57168(7) 0.3805(2) 0.0583(7) Uani d . . . 1 . .
H H26 1.0477 0.5941 0.3857 0.07 Uiso calc U . R 1 . .
C C27 1.1227(2) 0.55071(7) 0.4027(2) 0.0631(7) Uani d . . . 1 . .
H H27 1.1991 0.5588 0.42 0.076 Uiso calc U . R 1 . .
C C28 1.1046(2) 0.51691(7) 0.40038(18) 0.0512(6) Uani d . . . 1 . .
C C29 1.2015(2) 0.49509(8) 0.4295(2) 0.0628(7) Uani d . . . 1 . .
H H29 1.2777 0.5035 0.4481 0.075 Uiso calc U . R 1 . .
C C30 1.1871(2) 0.46262(8) 0.4312(2) 0.0641(8) Uani d . . . 1 . .
H H30 1.2522 0.4486 0.4495 0.077 Uiso calc U . R 1 . .
C C31 1.0746(2) 0.45015(7) 0.40536(19) 0.0583(7) Uani d . . . 1 . .
H H31 1.0646 0.4276 0.4084 0.07 Uiso calc U . R 1 . .
C C32 0.9784(2) 0.47012(6) 0.37567(18) 0.0491(6) Uani d . . . 1 . .
H H32 0.9035 0.461 0.3584 0.059 Uiso calc U . R 1 . .
C C33 0.9887(2) 0.50419(6) 0.37026(17) 0.0440(5) Uani d . . . 1 . .
C C34 0.89067(19) 0.52678(5) 0.34007(16) 0.0402(5) Uani d . . . 1 . .
C C35 0.6183(2) 0.60300(5) 0.2741(2) 0.0565(7) Uani d . . . 1 . .
H H35A 0.6598 0.6236 0.2933 0.085 Uiso calc U . R 1 . .
H H35B 0.5726 0.6 0.3142 0.085 Uiso calc U . R 1 . .
H H35C 0.5656 0.6029 0.1986 0.085 Uiso calc U . R 1 . .
C C36 0.51537(17) 0.43806(5) 0.19245(17) 0.0359(5) Uani d . . . 1 . .
C C37 0.5454(2) 0.41401(5) 0.27076(19) 0.0481(6) Uani d . . . 1 . .
C C38 0.5608(2) 0.38253(6) 0.2436(2) 0.0566(7) Uani d . . . 1 . .
H H38 0.5802 0.3662 0.2955 0.068 Uiso calc U . R 1 . .
C C39 0.5489(2) 0.37417(5) 0.1439(2) 0.0503(6) Uani d . . . 1 . .
C C40 0.5201(2) 0.39843(5) 0.0691(2) 0.0496(6) Uani d . . . 1 . .
H H40 0.5128 0.3932 0.001 0.06 Uiso calc U . R 1 . .
C C41 0.50156(19) 0.43025(5) 0.09041(18) 0.0408(5) Uani d . . . 1 . .
C C42 0.5603(3) 0.42227(7) 0.3807(2) 0.0823(9) Uani d . . . 1 . .
H H42A 0.6041 0.4424 0.4038 0.123 Uiso calc U . R 1 . .
H H42B 0.6034 0.405 0.4294 0.123 Uiso calc U . R 1 . .
H H42C 0.483 0.4247 0.3799 0.123 Uiso calc U . R 1 . .
C C43 0.5651(3) 0.33969(6) 0.1165(3) 0.0740(8) Uani d . . . 1 . .
H H43A 0.4947 0.3272 0.1041 0.111 Uiso calc U . R 1 . .
H H43B 0.6331 0.3302 0.1749 0.111 Uiso calc U . R 1 . .
H H43C 0.5778 0.3395 0.0528 0.111 Uiso calc U . R 1 . .
C C44 0.4644(3) 0.45546(6) 0.0043(2) 0.0578(7) Uani d . . . 1 . .
H H44A 0.4531 0.4453 -0.0621 0.087 Uiso calc U . R 1 . .
H H44B 0.5254 0.472 0.0234 0.087 Uiso calc U . R 1 . .
H H44C 0.3908 0.4654 -0.004 0.087 Uiso calc U . R 1 . .
C C45 -0.02361(19) 0.28826(5) 0.44231(17) 0.0401(5) Uani d . . . 1 . .
C C46 -0.07141(18) 0.25590(5) 0.43011(16) 0.0367(5) Uani d . . . 1 . .
C C47 0.02258(18) 0.23535(5) 0.44814(17) 0.0403(5) Uani d . . . 1 . .
H H47 0.019 0.2126 0.4449 0.048 Uiso calc U . R 1 . .
C C48 0.12305(18) 0.25399(5) 0.47190(18) 0.0398(5) Uani d . . . 1 . .
C C49 0.23684(19) 0.24303(5) 0.49570(18) 0.0416(5) Uani d . . . 1 . .
C C50 0.32819(19) 0.26514(5) 0.51396(18) 0.0431(5) Uani d . . . 1 . .
C C51 0.44793(19) 0.25893(5) 0.54634(18) 0.0448(5) Uani d . . . 1 . .
H H51 0.4837 0.2383 0.559 0.054 Uiso calc U . R 1 . .
C C52 0.5056(2) 0.28856(5) 0.55685(18) 0.0439(5) Uani d . . . 1 . .
C C53 0.4135(2) 0.31290(5) 0.52579(18) 0.0438(5) Uani d . . . 1 . .
C C54 -0.0974(2) 0.31605(5) 0.42542(19) 0.0483(6) Uani d . . . 1 . .
C C55 -0.2141(2) 0.30941(6) 0.39533(19) 0.0491(6) Uani d . . . 1 . .
H H55 -0.2649 0.3272 0.3844 0.059 Uiso calc U . R 1 . .
C C56 -0.2661(2) 0.27807(6) 0.37894(17) 0.0444(5) Uani d . . . 1 . .
C C57 -0.3911(2) 0.27509(7) 0.33925(19) 0.0548(6) Uani d . . . 1 . .
H H57 -0.4377 0.2939 0.3278 0.066 Uiso calc U . R 1 . .
C C58 -0.4436(2) 0.24576(7) 0.3179(2) 0.0601(7) Uani d . . . 1 . .
H H58 -0.5267 0.2445 0.2871 0.072 Uiso calc U . R 1 . .
C C59 -0.3758(2) 0.21673(6) 0.34077(18) 0.0502(6) Uani d . . . 1 . .
C C60 -0.4310(2) 0.18592(8) 0.3220(2) 0.0678(8) Uani d . . . 1 . .
H H60 -0.5142 0.1847 0.2904 0.081 Uiso calc U . R 1 . .
C C61 -0.3673(3) 0.15838(7) 0.3481(2) 0.0702(8) Uani d . . . 1 . .
H H61 -0.4057 0.1381 0.3334 0.084 Uiso calc U . R 1 . .
C C62 -0.2446(2) 0.15999(7) 0.3968(2) 0.0663(8) Uani d . . . 1 . .
H H62 -0.1998 0.1408 0.4178 0.08 Uiso calc U . R 1 . .
C C63 -0.1887(2) 0.18923(6) 0.4146(2) 0.0563(7) Uani d . . . 1 . .
H H63 -0.1054 0.1897 0.4477 0.068 Uiso calc U . R 1 . .
C C64 -0.25046(19) 0.21875(6) 0.38525(17) 0.0422(5) Uani d . . . 1 . .
C C65 -0.19588(18) 0.25025(5) 0.39895(16) 0.0383(5) Uani d . . . 1 . .
C C66 -0.0561(3) 0.35072(6) 0.4396(3) 0.0756(9) Uani d . . . 1 . .
H H66A -0.1221 0.365 0.4285 0.113 Uiso calc U . R 1 . .
H H66B -0.0258 0.3559 0.3883 0.113 Uiso calc U . R 1 . .
H H66C 0.0061 0.3537 0.511 0.113 Uiso calc U . R 1 . .
C C67 0.4386(2) 0.34659(6) 0.52249(19) 0.0516(6) Uani d . . . 1 . .
C C68 0.5558(2) 0.35403(6) 0.5618(2) 0.0586(7) Uani d . . . 1 . .
H H68 0.5758 0.3761 0.5662 0.07 Uiso calc U . R 1 . .
C C69 0.6507(2) 0.33131(6) 0.5968(2) 0.0543(6) Uani d . . . 1 . .
C C70 0.7680(3) 0.34351(8) 0.6341(2) 0.0697(8) Uani d . . . 1 . .
H H70 0.7815 0.366 0.6384 0.084 Uiso calc U . R 1 . .
C C71 0.8604(3) 0.32263(9) 0.6636(2) 0.0752(9) Uani d . . . 1 . .
H H71 0.9376 0.331 0.688 0.09 Uiso calc U . R 1 . .
C C72 0.8438(2) 0.28867(8) 0.6586(2) 0.0611(7) Uani d . . . 1 . .
C C73 0.9411(3) 0.26751(10) 0.6875(2) 0.0763(9) Uani d . . . 1 . .
H H73 1.0173 0.2764 0.7097 0.092 Uiso calc U . R 1 . .
C C74 0.9286(2) 0.23486(10) 0.6844(2) 0.0753(9) Uani d . . . 1 . .
H H74 0.995 0.2213 0.7042 0.09 Uiso calc U . R 1 . .
C C75 0.8158(2) 0.22169(8) 0.6515(2) 0.0662(8) Uani d . . . 1 . .
H H75 0.806 0.199 0.6498 0.079 Uiso calc U . R 1 . .
C C76 0.7190(2) 0.24156(7) 0.6215(2) 0.0578(7) Uani d . . . 1 . .
H H76 0.6436 0.2321 0.5984 0.069 Uiso calc U . R 1 . .
C C77 0.7278(2) 0.27561(6) 0.62404(18) 0.0493(6) Uani d . . . 1 . .
C C78 0.6288(2) 0.29774(6) 0.59256(18) 0.0471(6) Uani d . . . 1 . .
C C79 0.3479(3) 0.37307(6) 0.4762(2) 0.0692(8) Uani d . . . 1 . .
H H79A 0.3876 0.3939 0.4889 0.104 Uiso calc U . R 1 . .
H H79B 0.2945 0.3727 0.5097 0.104 Uiso calc U . R 1 . .
H H79C 0.3032 0.3697 0.4003 0.104 Uiso calc U . R 1 . .
C C80 0.25198(18) 0.20723(5) 0.49382(19) 0.0424(5) Uani d . . . 1 . .
C C81 0.24838(19) 0.18781(5) 0.57495(19) 0.0469(6) Uani d . . . 1 . .
C C82 0.2376(2) 0.15437(6) 0.5596(2) 0.0552(6) Uani d . . . 1 . .
H H82 0.2366 0.1412 0.614 0.066 Uiso calc U . R 1 . .
C C83 0.2283(2) 0.13989(6) 0.4666(2) 0.0573(7) Uani d . . . 1 . .
C C84 0.2389(2) 0.15935(6) 0.3912(2) 0.0561(7) Uani d . . . 1 . .
H H84 0.2378 0.1496 0.3299 0.067 Uiso calc U . R 1 . .
C C85 0.25128(19) 0.19276(5) 0.4023(2) 0.0460(6) Uani d . . . 1 . .
C C86 0.2553(3) 0.20189(6) 0.6768(2) 0.0657(7) Uani d . . . 1 . .
H H86A 0.1771 0.209 0.6661 0.099 Uiso calc U . R 1 . .
H H86B 0.3091 0.2202 0.698 0.099 Uiso calc U . R 1 . .
H H86C 0.284 0.1855 0.7322 0.099 Uiso calc U . R 1 . .
C C87 0.2052(3) 0.10400(6) 0.4484(3) 0.0827(10) Uani d . . . 1 . .
H H87A 0.1226 0.0996 0.4304 0.124 Uiso calc U . R 1 . .
H H87B 0.2552 0.0923 0.5127 0.124 Uiso calc U . R 1 . .
H H87C 0.2228 0.097 0.3906 0.124 Uiso calc U . R 1 . .
C C88 0.2620(2) 0.21285(7) 0.3172(2) 0.0636(7) Uani d . . . 1 . .
H H88A 0.2134 0.2322 0.3042 0.095 Uiso calc U . R 1 . .
H H88B 0.2355 0.2003 0.2522 0.095 Uiso calc U . R 1 . .
H H88C 0.3441 0.2191 0.3402 0.095 Uiso calc U . R 1 . .
F F1 0.40995(11) 0.56348(3) 0.15263(10) 0.0488(3) Uani d . . . 1 . .
F F2 0.45677(12) 0.55754(3) 0.32878(11) 0.0555(4) Uani d . . . 1 . .
F F3 0.19945(12) 0.33432(3) 0.56189(11) 0.0591(4) Uani d . . . 1 . .
F F4 0.14258(12) 0.33059(3) 0.38280(12) 0.0619(4) Uani d . . . 1 . .
N N1 0.35523(15) 0.51382(4) 0.20971(14) 0.0385(4) Uani d . . . 1 . .
N N2 0.56999(15) 0.52751(4) 0.25736(13) 0.0373(4) Uani d . . . 1 . .
N N3 0.09540(15) 0.28660(4) 0.46835(14) 0.0411(4) Uani d . . . 1 . .
N N4 0.30662(16) 0.29818(4) 0.50163(15) 0.0433(5) Uani d . . . 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 F2 . 1.380(3) ?
B1 F1 . 1.381(3) ?
B1 N2 . 1.565(3) ?
B1 N1 . 1.568(3) ?
B2 F4 . 1.379(3) ?
B2 F3 . 1.388(3) ?
B2 N4 . 1.555(3) ?
B2 N3 . 1.556(3) ?
C1 N1 . 1.379(3) ?
C1 C10 . 1.422(3) ?
C1 C2 . 1.442(3) ?
C2 C3 . 1.384(3) ?
C2 C21 . 1.447(3) ?
C3 C4 . 1.394(3) ?
C3 H3 . 0.94 ?
C4 N1 . 1.385(3) ?
C4 C5 . 1.391(3) ?
C5 C6 . 1.401(3) ?
C5 C36 . 1.489(3) ?
C6 N2 . 1.386(3) ?
C6 C7 . 1.387(3) ?
C7 C8 . 1.392(3) ?
C7 H7 . 0.94 ?
C8 C9 . 1.435(3) ?
C8 C34 . 1.448(3) ?
C9 N2 . 1.376(3) ?
C9 C23 . 1.431(3) ?
C10 C11 . 1.362(3) ?
C10 C22 . 1.503(3) ?
C11 C12 . 1.418(3) ?
C11 H11 . 0.94 ?
C12 C21 . 1.402(3) ?
C12 C13 . 1.418(3) ?
C13 C14 . 1.347(4) ?
C13 H13 . 0.94 ?
C14 C15 . 1.418(4) ?
C14 H14 . 0.94 ?
C15 C16 . 1.413(4) ?
C15 C20 . 1.421(3) ?
C16 C17 . 1.367(4) ?
C16 H16 . 0.94 ?
C17 C18 . 1.395(4) ?
C17 H17 . 0.94 ?
C18 C19 . 1.366(3) ?
C18 H18 . 0.94 ?
C19 C20 . 1.417(3) ?
C19 H19 . 0.94 ?
C20 C21 . 1.442(3) ?
C22 H22A . 0.97 ?
C22 H22B . 0.97 ?
C22 H22C . 0.97 ?
C23 C24 . 1.364(3) ?
C23 C35 . 1.495(3) ?
C24 C25 . 1.420(3) ?
C24 H24 . 0.94 ?
C25 C34 . 1.407(3) ?
C25 C26 . 1.425(3) ?
C26 C27 . 1.346(4) ?
C26 H26 . 0.94 ?
C27 C28 . 1.409(4) ?
C27 H27 . 0.94 ?
C28 C29 . 1.421(4) ?
C28 C33 . 1.425(3) ?
C29 C30 . 1.352(4) ?
C29 H29 . 0.94 ?
C30 C31 . 1.393(4) ?
C30 H30 . 0.94 ?
C31 C32 . 1.366(3) ?
C31 H31 . 0.94 ?
C32 C33 . 1.415(3) ?
C32 H32 . 0.94 ?
C33 C34 . 1.450(3) ?
C35 H35A . 0.97 ?
C35 H35B . 0.97 ?
C35 H35C . 0.97 ?
C36 C41 . 1.397(3) ?
C36 C37 . 1.400(3) ?
C37 C38 . 1.388(3) ?
C37 C42 . 1.504(4) ?
C38 C39 . 1.380(4) ?
C38 H38 . 0.94 ?
C39 C40 . 1.376(3) ?
C39 C43 . 1.508(3) ?
C40 C41 . 1.387(3) ?
C40 H40 . 0.94 ?
C41 C44 . 1.502(3) ?
C42 H42A . 0.97 ?
C42 H42B . 0.97 ?
C42 H42C . 0.97 ?
C43 H43A . 0.97 ?
C43 H43B . 0.97 ?
C43 H43C . 0.97 ?
C44 H44A . 0.97 ?
C44 H44B . 0.97 ?
C44 H44C . 0.97 ?
C45 N3 . 1.375(3) ?
C45 C54 . 1.426(3) ?
C45 C46 . 1.441(3) ?
C46 C47 . 1.382(3) ?
C46 C65 . 1.445(3) ?
C47 C48 . 1.387(3) ?
C47 H47 . 0.94 ?
C48 N3 . 1.383(3) ?
C48 C49 . 1.392(3) ?
C49 C50 . 1.397(3) ?
C49 C80 . 1.489(3) ?
C50 N4 . 1.384(3) ?
C50 C51 . 1.390(3) ?
C51 C52 . 1.394(3) ?
C51 H51 . 0.94 ?
C52 C53 . 1.446(3) ?
C52 C78 . 1.451(3) ?
C53 N4 . 1.373(3) ?
C53 C67 . 1.428(3) ?
C54 C55 . 1.363(3) ?
C54 C66 . 1.503(3) ?
C55 C56 . 1.420(3) ?
C55 H55 . 0.94 ?
C56 C65 . 1.398(3) ?
C56 C57 . 1.421(3) ?
C57 C58 . 1.346(4) ?
C57 H57 . 0.94 ?
C58 C59 . 1.421(4) ?
C58 H58 . 0.94 ?
C59 C60 . 1.415(4) ?
C59 C64 . 1.419(3) ?
C60 C61 . 1.343(4) ?
C60 H60 . 0.94 ?
C61 C62 . 1.386(4) ?
C61 H61 . 0.94 ?
C62 C63 . 1.361(3) ?
C62 H62 . 0.94 ?
C63 C64 . 1.404(3) ?
C63 H63 . 0.94 ?
C64 C65 . 1.440(3) ?
C66 H66A . 0.97 ?
C66 H66B . 0.97 ?
C66 H66C . 0.97 ?
C67 C68 . 1.361(3) ?
C67 C79 . 1.503(4) ?
C68 C69 . 1.423(4) ?
C68 H68 . 0.94 ?
C69 C78 . 1.406(3) ?
C69 C70 . 1.421(3) ?
C70 C71 . 1.355(4) ?
C70 H70 . 0.94 ?
C71 C72 . 1.412(4) ?
C71 H71 . 0.94 ?
C72 C73 . 1.408(4) ?
C72 C77 . 1.423(3) ?
C73 C74 . 1.353(4) ?
C73 H73 . 0.94 ?
C74 C75 . 1.393(4) ?
C74 H74 . 0.94 ?
C75 C76 . 1.370(4) ?
C75 H75 . 0.94 ?
C76 C77 . 1.407(3) ?
C76 H76 . 0.94 ?
C77 C78 . 1.446(3) ?
C79 H79A . 0.97 ?
C79 H79B . 0.97 ?
C79 H79C . 0.97 ?
C80 C81 . 1.404(3) ?
C80 C85 . 1.407(3) ?
C81 C82 . 1.392(3) ?
C81 C86 . 1.505(3) ?
C82 C83 . 1.388(4) ?
C82 H82 . 0.94 ?
C83 C84 . 1.376(4) ?
C83 C87 . 1.507(3) ?
C84 C85 . 1.387(3) ?
C84 H84 . 0.94 ?
C85 C88 . 1.503(3) ?
C86 H86A . 0.97 ?
C86 H86B . 0.97 ?
C86 H86C . 0.97 ?
C87 H87A . 0.97 ?
C87 H87B . 0.97 ?
C87 H87C . 0.97 ?
C88 H88A . 0.97 ?
C88 H88B . 0.97 ?
C88 H88C . 0.97 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F2 B1 F1 . . 111.38(18) ?
F2 B1 N2 . . 109.31(18) ?
F1 B1 N2 . . 109.57(18) ?
F2 B1 N1 . . 109.20(18) ?
F1 B1 N1 . . 108.97(18) ?
N2 B1 N1 . . 108.36(17) ?
F4 B2 F3 . . 111.58(19) ?
F4 B2 N4 . . 110.1(2) ?
F3 B2 N4 . . 108.61(19) ?
F4 B2 N3 . . 108.43(19) ?
F3 B2 N3 . . 109.5(2) ?
N4 B2 N3 . . 108.65(17) ?
N1 C1 C10 . . 129.31(19) ?
N1 C1 C2 . . 109.29(17) ?
C10 C1 C2 . . 121.2(2) ?
C3 C2 C1 . . 105.87(18) ?
C3 C2 C21 . . 132.8(2) ?
C1 C2 C21 . . 121.27(19) ?
C2 C3 C4 . . 108.17(18) ?
C2 C3 H3 . . 125.9 ?
C4 C3 H3 . . 125.9 ?
N1 C4 C5 . . 122.29(19) ?
N1 C4 C3 . . 110.07(18) ?
C5 C4 C3 . . 127.64(19) ?
C4 C5 C6 . . 120.47(19) ?
C4 C5 C36 . . 119.60(18) ?
C6 C5 C36 . . 119.85(18) ?
N2 C6 C7 . . 110.41(18) ?
N2 C6 C5 . . 121.92(19) ?
C7 C6 C5 . . 127.65(19) ?
C6 C7 C8 . . 107.99(19) ?
C6 C7 H7 . . 126.0 ?
C8 C7 H7 . . 126.0 ?
C7 C8 C9 . . 105.52(18) ?
C7 C8 C34 . . 133.1(2) ?
C9 C8 C34 . . 121.36(19) ?
N2 C9 C23 . . 128.6(2) ?
N2 C9 C8 . . 109.84(17) ?
C23 C9 C8 . . 121.49(19) ?
C11 C10 C1 . . 114.8(2) ?
C11 C10 C22 . . 119.5(2) ?
C1 C10 C22 . . 125.7(2) ?
C10 C11 C12 . . 126.5(2) ?
C10 C11 H11 . . 116.8 ?
C12 C11 H11 . . 116.8 ?
C21 C12 C11 . . 120.0(2) ?
C21 C12 C13 . . 120.2(2) ?
C11 C12 C13 . . 119.7(2) ?
C14 C13 C12 . . 121.0(2) ?
C14 C13 H13 . . 119.5 ?
C12 C13 H13 . . 119.5 ?
C13 C14 C15 . . 120.9(2) ?
C13 C14 H14 . . 119.6 ?
C15 C14 H14 . . 119.6 ?
C16 C15 C14 . . 120.4(2) ?
C16 C15 C20 . . 119.6(3) ?
C14 C15 C20 . . 119.9(2) ?
C17 C16 C15 . . 120.9(3) ?
C17 C16 H16 . . 119.5 ?
C15 C16 H16 . . 119.5 ?
C16 C17 C18 . . 120.1(3) ?
C16 C17 H17 . . 120.0 ?
C18 C17 H17 . . 120.0 ?
C19 C18 C17 . . 120.1(3) ?
C19 C18 H18 . . 119.9 ?
C17 C18 H18 . . 119.9 ?
C18 C19 C20 . . 122.1(2) ?
C18 C19 H19 . . 119.0 ?
C20 C19 H19 . . 119.0 ?
C19 C20 C15 . . 117.1(2) ?
C19 C20 C21 . . 124.2(2) ?
C15 C20 C21 . . 118.5(2) ?
C12 C21 C20 . . 119.0(2) ?
C12 C21 C2 . . 115.5(2) ?
C20 C21 C2 . . 125.4(2) ?
C10 C22 H22A . . 109.5 ?
C10 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C10 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C24 C23 C9 . . 114.8(2) ?
C24 C23 C35 . . 119.7(2) ?
C9 C23 C35 . . 125.3(2) ?
C23 C24 C25 . . 126.1(2) ?
C23 C24 H24 . . 117.0 ?
C25 C24 H24 . . 117.0 ?
C34 C25 C24 . . 120.5(2) ?
C34 C25 C26 . . 120.4(2) ?
C24 C25 C26 . . 119.1(2) ?
C27 C26 C25 . . 120.8(2) ?
C27 C26 H26 . . 119.6 ?
C25 C26 H26 . . 119.6 ?
C26 C27 C28 . . 121.2(2) ?
C26 C27 H27 . . 119.4 ?
C28 C27 H27 . . 119.4 ?
C27 C28 C29 . . 120.6(2) ?
C27 C28 C33 . . 120.3(2) ?
C29 C28 C33 . . 119.1(2) ?
C30 C29 C28 . . 121.8(3) ?
C30 C29 H29 . . 119.1 ?
C28 C29 H29 . . 119.1 ?
C29 C30 C31 . . 119.2(3) ?
C29 C30 H30 . . 120.4 ?
C31 C30 H30 . . 120.4 ?
C32 C31 C30 . . 121.1(3) ?
C32 C31 H31 . . 119.4 ?
C30 C31 H31 . . 119.4 ?
C31 C32 C33 . . 121.6(2) ?
C31 C32 H32 . . 119.2 ?
C33 C32 H32 . . 119.2 ?
C32 C33 C28 . . 117.0(2) ?
C32 C33 C34 . . 124.5(2) ?
C28 C33 C34 . . 118.4(2) ?
C25 C34 C8 . . 115.5(2) ?
C25 C34 C33 . . 118.7(2) ?
C8 C34 C33 . . 125.8(2) ?
C23 C35 H35A . . 109.5 ?
C23 C35 H35B . . 109.5 ?
H35A C35 H35B . . 109.5 ?
C23 C35 H35C . . 109.5 ?
H35A C35 H35C . . 109.5 ?
H35B C35 H35C . . 109.5 ?
C41 C36 C37 . . 120.40(19) ?
C41 C36 C5 . . 118.92(18) ?
C37 C36 C5 . . 120.7(2) ?
C38 C37 C36 . . 118.0(2) ?
C38 C37 C42 . . 121.4(2) ?
C36 C37 C42 . . 120.6(2) ?
C39 C38 C37 . . 122.9(2) ?
C39 C38 H38 . . 118.6 ?
C37 C38 H38 . . 118.6 ?
C40 C39 C38 . . 117.6(2) ?
C40 C39 C43 . . 120.7(2) ?
C38 C39 C43 . . 121.7(2) ?
C39 C40 C41 . . 122.5(2) ?
C39 C40 H40 . . 118.8 ?
C41 C40 H40 . . 118.8 ?
C40 C41 C36 . . 118.7(2) ?
C40 C41 C44 . . 120.3(2) ?
C36 C41 C44 . . 121.03(19) ?
C37 C42 H42A . . 109.5 ?
C37 C42 H42B . . 109.5 ?
H42A C42 H42B . . 109.5 ?
C37 C42 H42C . . 109.5 ?
H42A C42 H42C . . 109.5 ?
H42B C42 H42C . . 109.5 ?
C39 C43 H43A . . 109.5 ?
C39 C43 H43B . . 109.5 ?
H43A C43 H43B . . 109.5 ?
C39 C43 H43C . . 109.5 ?
H43A C43 H43C . . 109.5 ?
H43B C43 H43C . . 109.5 ?
C41 C44 H44A . . 109.5 ?
C41 C44 H44B . . 109.5 ?
H44A C44 H44B . . 109.5 ?
C41 C44 H44C . . 109.5 ?
H44A C44 H44C . . 109.5 ?
H44B C44 H44C . . 109.5 ?
N3 C45 C54 . . 129.4(2) ?
N3 C45 C46 . . 109.43(17) ?
C54 C45 C46 . . 121.1(2) ?
C47 C46 C45 . . 105.52(18) ?
C47 C46 C65 . . 132.8(2) ?
C45 C46 C65 . . 121.59(19) ?
C46 C47 C48 . . 108.54(18) ?
C46 C47 H47 . . 125.7 ?
C48 C47 H47 . . 125.7 ?
N3 C48 C47 . . 110.00(18) ?
N3 C48 C49 . . 122.59(19) ?
C47 C48 C49 . . 127.41(19) ?
C48 C49 C50 . . 120.39(19) ?
C48 C49 C80 . . 116.27(18) ?
C50 C49 C80 . . 123.24(19) ?
N4 C50 C51 . . 110.25(18) ?
N4 C50 C49 . . 121.21(19) ?
C51 C50 C49 . . 128.5(2) ?
C50 C51 C52 . . 108.1(2) ?
C50 C51 H51 . . 125.9 ?
C52 C51 H51 . . 125.9 ?
C51 C52 C53 . . 105.40(19) ?
C51 C52 C78 . . 133.7(2) ?
C53 C52 C78 . . 120.9(2) ?
N4 C53 C67 . . 128.8(2) ?
N4 C53 C52 . . 109.51(18) ?
C67 C53 C52 . . 121.7(2) ?
C55 C54 C45 . . 115.0(2) ?
C55 C54 C66 . . 119.5(2) ?
C45 C54 C66 . . 125.5(2) ?
C54 C55 C56 . . 126.1(2) ?
C54 C55 H55 . . 117.0 ?
C56 C55 H55 . . 117.0 ?
C65 C56 C55 . . 120.6(2) ?
C65 C56 C57 . . 119.9(2) ?
C55 C56 C57 . . 119.5(2) ?
C58 C57 C56 . . 120.9(2) ?
C58 C57 H57 . . 119.6 ?
C56 C57 H57 . . 119.6 ?
C57 C58 C59 . . 121.3(2) ?
C57 C58 H58 . . 119.4 ?
C59 C58 H58 . . 119.4 ?
C60 C59 C64 . . 119.5(2) ?
C60 C59 C58 . . 121.2(2) ?
C64 C59 C58 . . 119.3(2) ?
C61 C60 C59 . . 121.5(2) ?
C61 C60 H60 . . 119.2 ?
C59 C60 H60 . . 119.2 ?
C60 C61 C62 . . 119.6(3) ?
C60 C61 H61 . . 120.2 ?
C62 C61 H61 . . 120.2 ?
C63 C62 C61 . . 120.4(3) ?
C63 C62 H62 . . 119.8 ?
C61 C62 H62 . . 119.8 ?
C62 C63 C64 . . 122.6(2) ?
C62 C63 H63 . . 118.7 ?
C64 C63 H63 . . 118.7 ?
C63 C64 C59 . . 116.2(2) ?
C63 C64 C65 . . 124.9(2) ?
C59 C64 C65 . . 118.9(2) ?
C56 C65 C64 . . 119.4(2) ?
C56 C65 C46 . . 115.58(19) ?
C64 C65 C46 . . 125.01(19) ?
C54 C66 H66A . . 109.5 ?
C54 C66 H66B . . 109.5 ?
H66A C66 H66B . . 109.5 ?
C54 C66 H66C . . 109.5 ?
H66A C66 H66C . . 109.5 ?
H66B C66 H66C . . 109.5 ?
C68 C67 C53 . . 114.8(2) ?
C68 C67 C79 . . 119.4(2) ?
C53 C67 C79 . . 125.7(2) ?
C67 C68 C69 . . 125.8(2) ?
C67 C68 H68 . . 117.1 ?
C69 C68 H68 . . 117.1 ?
C78 C69 C70 . . 121.0(3) ?
C78 C69 C68 . . 120.9(2) ?
C70 C69 C68 . . 118.1(2) ?
C71 C70 C69 . . 119.9(3) ?
C71 C70 H70 . . 120.1 ?
C69 C70 H70 . . 120.1 ?
C70 C71 C72 . . 121.8(3) ?
C70 C71 H71 . . 119.1 ?
C72 C71 H71 . . 119.1 ?
C73 C72 C71 . . 120.6(3) ?
C73 C72 C77 . . 119.5(3) ?
C71 C72 C77 . . 119.9(3) ?
C74 C73 C72 . . 122.2(3) ?
C74 C73 H73 . . 118.9 ?
C72 C73 H73 . . 118.9 ?
C73 C74 C75 . . 119.0(3) ?
C73 C74 H74 . . 120.5 ?
C75 C74 H74 . . 120.5 ?
C76 C75 C74 . . 120.3(3) ?
C76 C75 H75 . . 119.8 ?
C74 C75 H75 . . 119.8 ?
C75 C76 C77 . . 122.6(2) ?
C75 C76 H76 . . 118.7 ?
C77 C76 H76 . . 118.7 ?
C76 C77 C72 . . 116.3(2) ?
C76 C77 C78 . . 125.0(2) ?
C72 C77 C78 . . 118.7(2) ?
C69 C78 C77 . . 118.8(2) ?
C69 C78 C52 . . 115.5(2) ?
C77 C78 C52 . . 125.7(2) ?
C67 C79 H79A . . 109.5 ?
C67 C79 H79B . . 109.5 ?
H79A C79 H79B . . 109.5 ?
C67 C79 H79C . . 109.5 ?
H79A C79 H79C . . 109.5 ?
H79B C79 H79C . . 109.5 ?
C81 C80 C85 . . 120.2(2) ?
C81 C80 C49 . . 120.1(2) ?
C85 C80 C49 . . 119.0(2) ?
C82 C81 C80 . . 118.3(2) ?
C82 C81 C86 . . 119.3(2) ?
C80 C81 C86 . . 122.4(2) ?
C83 C82 C81 . . 122.2(2) ?
C83 C82 H82 . . 118.9 ?
C81 C82 H82 . . 118.9 ?
C84 C83 C82 . . 118.0(2) ?
C84 C83 C87 . . 121.3(3) ?
C82 C83 C87 . . 120.7(3) ?
C83 C84 C85 . . 122.4(2) ?
C83 C84 H84 . . 118.8 ?
C85 C84 H84 . . 118.8 ?
C84 C85 C80 . . 118.6(2) ?
C84 C85 C88 . . 120.2(2) ?
C80 C85 C88 . . 121.3(2) ?
C81 C86 H86A . . 109.5 ?
C81 C86 H86B . . 109.5 ?
H86A C86 H86B . . 109.5 ?
C81 C86 H86C . . 109.5 ?
H86A C86 H86C . . 109.5 ?
H86B C86 H86C . . 109.5 ?
C83 C87 H87A . . 109.5 ?
C83 C87 H87B . . 109.5 ?
H87A C87 H87B . . 109.5 ?
C83 C87 H87C . . 109.5 ?
H87A C87 H87C . . 109.5 ?
H87B C87 H87C . . 109.5 ?
C85 C88 H88A . . 109.5 ?
C85 C88 H88B . . 109.5 ?
H88A C88 H88B . . 109.5 ?
C85 C88 H88C . . 109.5 ?
H88A C88 H88C . . 109.5 ?
H88B C88 H88C . . 109.5 ?
C1 N1 C4 . . 106.48(16) ?
C1 N1 B1 . . 130.18(17) ?
C4 N1 B1 . . 123.32(17) ?
C9 N2 C6 . . 106.05(17) ?
C9 N2 B1 . . 130.50(17) ?
C6 N2 B1 . . 123.45(17) ?
C45 N3 C48 . . 106.50(17) ?
C45 N3 B2 . . 130.29(17) ?
C48 N3 B2 . . 122.71(18) ?
C53 N4 C50 . . 106.68(18) ?
C53 N4 B2 . . 129.00(18) ?
C50 N4 B2 . . 123.94(17) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . -3.4(2) ?
C10 C1 C2 C3 . . . . 172.0(2) ?
N1 C1 C2 C21 . . . . 179.43(18) ?
C10 C1 C2 C21 . . . . -5.1(3) ?
C1 C2 C3 C4 . . . . 2.1(2) ?
C21 C2 C3 C4 . . . . 178.8(2) ?
C2 C3 C4 N1 . . . . -0.1(2) ?
C2 C3 C4 C5 . . . . -179.8(2) ?
N1 C4 C5 C6 . . . . 4.6(3) ?
C3 C4 C5 C6 . . . . -175.8(2) ?
N1 C4 C5 C36 . . . . -172.17(19) ?
C3 C4 C5 C36 . . . . 7.5(3) ?
C4 C5 C6 N2 . . . . -4.2(3) ?
C36 C5 C6 N2 . . . . 172.55(18) ?
C4 C5 C6 C7 . . . . 174.2(2) ?
C36 C5 C6 C7 . . . . -9.1(3) ?
N2 C6 C7 C8 . . . . 1.2(2) ?
C5 C6 C7 C8 . . . . -177.3(2) ?
C6 C7 C8 C9 . . . . -3.3(2) ?
C6 C7 C8 C34 . . . . 178.3(2) ?
C7 C8 C9 N2 . . . . 4.4(2) ?
C34 C8 C9 N2 . . . . -176.99(17) ?
C7 C8 C9 C23 . . . . -172.42(18) ?
C34 C8 C9 C23 . . . . 6.2(3) ?
N1 C1 C10 C11 . . . . 172.8(2) ?
C2 C1 C10 C11 . . . . -1.7(3) ?
N1 C1 C10 C22 . . . . -5.6(4) ?
C2 C1 C10 C22 . . . . 179.9(2) ?
C1 C10 C11 C12 . . . . 3.8(3) ?
C22 C10 C11 C12 . . . . -177.7(2) ?
C10 C11 C12 C21 . . . . 1.0(4) ?
C10 C11 C12 C13 . . . . 179.2(2) ?
C21 C12 C13 C14 . . . . 1.0(3) ?
C11 C12 C13 C14 . . . . -177.2(2) ?
C12 C13 C14 C15 . . . . 4.4(4) ?
C13 C14 C15 C16 . . . . 172.5(2) ?
C13 C14 C15 C20 . . . . -4.0(4) ?
C14 C15 C16 C17 . . . . -174.8(3) ?
C20 C15 C16 C17 . . . . 1.8(4) ?
C15 C16 C17 C18 . . . . 0.5(5) ?
C16 C17 C18 C19 . . . . -1.8(5) ?
C17 C18 C19 C20 . . . . 0.8(4) ?
C18 C19 C20 C15 . . . . 1.4(4) ?
C18 C19 C20 C21 . . . . 176.5(2) ?
C16 C15 C20 C19 . . . . -2.7(3) ?
C14 C15 C20 C19 . . . . 173.9(2) ?
C16 C15 C20 C21 . . . . -178.1(2) ?
C14 C15 C20 C21 . . . . -1.5(3) ?
C11 C12 C21 C20 . . . . 171.74(19) ?
C13 C12 C21 C20 . . . . -6.5(3) ?
C11 C12 C21 C2 . . . . -7.5(3) ?
C13 C12 C21 C2 . . . . 174.25(19) ?
C19 C20 C21 C12 . . . . -168.4(2) ?
C15 C20 C21 C12 . . . . 6.6(3) ?
C19 C20 C21 C2 . . . . 10.8(3) ?
C15 C20 C21 C2 . . . . -174.2(2) ?
C3 C2 C21 C12 . . . . -166.7(2) ?
C1 C2 C21 C12 . . . . 9.5(3) ?
C3 C2 C21 C20 . . . . 14.1(4) ?
C1 C2 C21 C20 . . . . -169.69(19) ?
N2 C9 C23 C24 . . . . -178.6(2) ?
C8 C9 C23 C24 . . . . -2.4(3) ?
N2 C9 C23 C35 . . . . -2.8(4) ?
C8 C9 C23 C35 . . . . 173.4(2) ?
C9 C23 C24 C25 . . . . -0.8(3) ?
C35 C23 C24 C25 . . . . -176.8(2) ?
C23 C24 C25 C34 . . . . 0.3(4) ?
C23 C24 C25 C26 . . . . -179.4(2) ?
C34 C25 C26 C27 . . . . -0.7(4) ?
C24 C25 C26 C27 . . . . 178.9(2) ?
C25 C26 C27 C28 . . . . -2.8(4) ?
C26 C27 C28 C29 . . . . -176.6(2) ?
C26 C27 C28 C33 . . . . 2.5(4) ?
C27 C28 C29 C30 . . . . 177.9(2) ?
C33 C28 C29 C30 . . . . -1.1(4) ?
C28 C29 C30 C31 . . . . -1.1(4) ?
C29 C30 C31 C32 . . . . 1.8(4) ?
C30 C31 C32 C33 . . . . -0.3(4) ?
C31 C32 C33 C28 . . . . -1.9(3) ?
C31 C32 C33 C34 . . . . -179.6(2) ?
C27 C28 C33 C32 . . . . -176.5(2) ?
C29 C28 C33 C32 . . . . 2.6(3) ?
C27 C28 C33 C34 . . . . 1.3(3) ?
C29 C28 C33 C34 . . . . -179.6(2) ?
C24 C25 C34 C8 . . . . 3.3(3) ?
C26 C25 C34 C8 . . . . -177.1(2) ?
C24 C25 C34 C33 . . . . -175.19(19) ?
C26 C25 C34 C33 . . . . 4.5(3) ?
C7 C8 C34 C25 . . . . 171.8(2) ?
C9 C8 C34 C25 . . . . -6.3(3) ?
C7 C8 C34 C33 . . . . -9.9(4) ?
C9 C8 C34 C33 . . . . 171.97(19) ?
C32 C33 C34 C25 . . . . 172.9(2) ?
C28 C33 C34 C25 . . . . -4.7(3) ?
C32 C33 C34 C8 . . . . -5.3(3) ?
C28 C33 C34 C8 . . . . 177.02(19) ?
C4 C5 C36 C41 . . . . 91.1(2) ?
C6 C5 C36 C41 . . . . -85.6(3) ?
C4 C5 C36 C37 . . . . -87.7(3) ?
C6 C5 C36 C37 . . . . 95.6(2) ?
C41 C36 C37 C38 . . . . 0.0(3) ?
C5 C36 C37 C38 . . . . 178.8(2) ?
C41 C36 C37 C42 . . . . -180.0(2) ?
C5 C36 C37 C42 . . . . -1.2(3) ?
C36 C37 C38 C39 . . . . 0.6(4) ?
C42 C37 C38 C39 . . . . -179.4(3) ?
C37 C38 C39 C40 . . . . -0.2(4) ?
C37 C38 C39 C43 . . . . -179.4(2) ?
C38 C39 C40 C41 . . . . -1.0(4) ?
C43 C39 C40 C41 . . . . 178.3(2) ?
C39 C40 C41 C36 . . . . 1.6(3) ?
C39 C40 C41 C44 . . . . -176.9(2) ?
C37 C36 C41 C40 . . . . -1.1(3) ?
C5 C36 C41 C40 . . . . -179.86(19) ?
C37 C36 C41 C44 . . . . 177.4(2) ?
C5 C36 C41 C44 . . . . -1.4(3) ?
N3 C45 C46 C47 . . . . -0.9(2) ?
C54 C45 C46 C47 . . . . 177.7(2) ?
N3 C45 C46 C65 . . . . -177.75(18) ?
C54 C45 C46 C65 . . . . 0.9(3) ?
C45 C46 C47 C48 . . . . 1.0(2) ?
C65 C46 C47 C48 . . . . 177.3(2) ?
C46 C47 C48 N3 . . . . -0.7(3) ?
C46 C47 C48 C49 . . . . 179.7(2) ?
N3 C48 C49 C50 . . . . -2.0(3) ?
C47 C48 C49 C50 . . . . 177.5(2) ?
N3 C48 C49 C80 . . . . -178.5(2) ?
C47 C48 C49 C80 . . . . 1.0(3) ?
C48 C49 C50 N4 . . . . -4.6(3) ?
C80 C49 C50 N4 . . . . 171.6(2) ?
C48 C49 C50 C51 . . . . 174.6(2) ?
C80 C49 C50 C51 . . . . -9.1(4) ?
N4 C50 C51 C52 . . . . 0.9(3) ?
C49 C50 C51 C52 . . . . -178.4(2) ?
C50 C51 C52 C53 . . . . -1.8(2) ?
C50 C51 C52 C78 . . . . 176.4(2) ?
C51 C52 C53 N4 . . . . 2.0(2) ?
C78 C52 C53 N4 . . . . -176.38(19) ?
C51 C52 C53 C67 . . . . -177.6(2) ?
C78 C52 C53 C67 . . . . 4.0(3) ?
N3 C45 C54 C55 . . . . 177.0(2) ?
C46 C45 C54 C55 . . . . -1.3(3) ?
N3 C45 C54 C66 . . . . -3.9(4) ?
C46 C45 C54 C66 . . . . 177.8(2) ?
C45 C54 C55 C56 . . . . -0.7(4) ?
C66 C54 C55 C56 . . . . -179.9(2) ?
C54 C55 C56 C65 . . . . 3.4(4) ?
C54 C55 C56 C57 . . . . -175.0(2) ?
C65 C56 C57 C58 . . . . -1.8(3) ?
C55 C56 C57 C58 . . . . 176.7(2) ?
C56 C57 C58 C59 . . . . 4.3(4) ?
C57 C58 C59 C60 . . . . 177.6(2) ?
C57 C58 C59 C64 . . . . -1.2(4) ?
C64 C59 C60 C61 . . . . 2.0(4) ?
C58 C59 C60 C61 . . . . -176.8(3) ?
C59 C60 C61 C62 . . . . 1.5(4) ?
C60 C61 C62 C63 . . . . -2.5(4) ?
C61 C62 C63 C64 . . . . 0.0(4) ?
C62 C63 C64 C59 . . . . 3.3(4) ?
C62 C63 C64 C65 . . . . -177.9(2) ?
C60 C59 C64 C63 . . . . -4.2(3) ?
C58 C59 C64 C63 . . . . 174.6(2) ?
C60 C59 C64 C65 . . . . 176.9(2) ?
C58 C59 C64 C65 . . . . -4.3(3) ?
C55 C56 C65 C64 . . . . 177.8(2) ?
C57 C56 C65 C64 . . . . -3.8(3) ?
C55 C56 C65 C46 . . . . -3.6(3) ?
C57 C56 C65 C46 . . . . 174.74(19) ?
C63 C64 C65 C56 . . . . -172.0(2) ?
C59 C64 C65 C56 . . . . 6.7(3) ?
C63 C64 C65 C46 . . . . 9.6(3) ?
C59 C64 C65 C46 . . . . -171.7(2) ?
C47 C46 C65 C56 . . . . -174.2(2) ?
C45 C46 C65 C56 . . . . 1.7(3) ?
C47 C46 C65 C64 . . . . 4.2(4) ?
C45 C46 C65 C64 . . . . -179.9(2) ?
N4 C53 C67 C68 . . . . 173.5(2) ?
C52 C53 C67 C68 . . . . -7.0(3) ?
N4 C53 C67 C79 . . . . -9.2(4) ?
C52 C53 C67 C79 . . . . 170.3(2) ?
C53 C67 C68 C69 . . . . 5.0(4) ?
C79 C67 C68 C69 . . . . -172.5(2) ?
C67 C68 C69 C78 . . . . 0.3(4) ?
C67 C68 C69 C70 . . . . 179.1(2) ?
C78 C69 C70 C71 . . . . 1.8(4) ?
C68 C69 C70 C71 . . . . -177.0(3) ?
C69 C70 C71 C72 . . . . -0.2(4) ?
C70 C71 C72 C73 . . . . 178.6(3) ?
C70 C71 C72 C77 . . . . -1.3(4) ?
C71 C72 C73 C74 . . . . 179.6(3) ?
C77 C72 C73 C74 . . . . -0.5(4) ?
C72 C73 C74 C75 . . . . 0.1(4) ?
C73 C74 C75 C76 . . . . 0.7(4) ?
C74 C75 C76 C77 . . . . -1.1(4) ?
C75 C76 C77 C72 . . . . 0.6(4) ?
C75 C76 C77 C78 . . . . 179.4(2) ?
C73 C72 C77 C76 . . . . 0.2(3) ?
C71 C72 C77 C76 . . . . -179.9(2) ?
C73 C72 C77 C78 . . . . -178.7(2) ?
C71 C72 C77 C78 . . . . 1.2(3) ?
C70 C69 C78 C77 . . . . -1.8(3) ?
C68 C69 C78 C77 . . . . 176.9(2) ?
C70 C69 C78 C52 . . . . 177.7(2) ?
C68 C69 C78 C52 . . . . -3.6(3) ?
C76 C77 C78 C69 . . . . -178.5(2) ?
C72 C77 C78 C69 . . . . 0.3(3) ?
C76 C77 C78 C52 . . . . 2.1(4) ?
C72 C77 C78 C52 . . . . -179.1(2) ?
C51 C52 C78 C69 . . . . -176.4(2) ?
C53 C52 C78 C69 . . . . 1.5(3) ?
C51 C52 C78 C77 . . . . 3.0(4) ?
C53 C52 C78 C77 . . . . -179.1(2) ?
C48 C49 C80 C81 . . . . -72.4(3) ?
C50 C49 C80 C81 . . . . 111.2(3) ?
C48 C49 C80 C85 . . . . 97.8(2) ?
C50 C49 C80 C85 . . . . -78.6(3) ?
C85 C80 C81 C82 . . . . -3.5(3) ?
C49 C80 C81 C82 . . . . 166.6(2) ?
C85 C80 C81 C86 . . . . 176.8(2) ?
C49 C80 C81 C86 . . . . -13.1(3) ?
C80 C81 C82 C83 . . . . -1.1(3) ?
C86 C81 C82 C83 . . . . 178.6(2) ?
C81 C82 C83 C84 . . . . 4.8(4) ?
C81 C82 C83 C87 . . . . -174.2(2) ?
C82 C83 C84 C85 . . . . -4.0(4) ?
C87 C83 C84 C85 . . . . 175.0(2) ?
C83 C84 C85 C80 . . . . -0.5(4) ?
C83 C84 C85 C88 . . . . -179.7(2) ?
C81 C80 C85 C84 . . . . 4.3(3) ?
C49 C80 C85 C84 . . . . -165.9(2) ?
C81 C80 C85 C88 . . . . -176.5(2) ?
C49 C80 C85 C88 . . . . 13.3(3) ?
C10 C1 N1 C4 . . . . -171.6(2) ?
C2 C1 N1 C4 . . . . 3.4(2) ?
C10 C1 N1 B1 . . . . 7.1(4) ?
C2 C1 N1 B1 . . . . -177.88(19) ?
C5 C4 N1 C1 . . . . 177.65(19) ?
C3 C4 N1 C1 . . . . -2.1(2) ?
C5 C4 N1 B1 . . . . -1.2(3) ?
C3 C4 N1 B1 . . . . 179.09(18) ?
F2 B1 N1 C1 . . . . 60.3(3) ?
F1 B1 N1 C1 . . . . -61.5(3) ?
N2 B1 N1 C1 . . . . 179.32(18) ?
F2 B1 N1 C4 . . . . -121.1(2) ?
F1 B1 N1 C4 . . . . 117.1(2) ?
N2 B1 N1 C4 . . . . -2.1(3) ?
C23 C9 N2 C6 . . . . 172.9(2) ?
C8 C9 N2 C6 . . . . -3.7(2) ?
C23 C9 N2 B1 . . . . -7.5(3) ?
C8 C9 N2 B1 . . . . 175.99(19) ?
C7 C6 N2 C9 . . . . 1.6(2) ?
C5 C6 N2 C9 . . . . -179.85(19) ?
C7 C6 N2 B1 . . . . -178.14(18) ?
C5 C6 N2 B1 . . . . 0.4(3) ?
F2 B1 N2 C9 . . . . -58.3(3) ?
F1 B1 N2 C9 . . . . 64.1(3) ?
N1 B1 N2 C9 . . . . -177.16(18) ?
F2 B1 N2 C6 . . . . 121.4(2) ?
F1 B1 N2 C6 . . . . -116.3(2) ?
N1 B1 N2 C6 . . . . 2.5(3) ?
C54 C45 N3 C48 . . . . -178.0(2) ?
C46 C45 N3 C48 . . . . 0.5(2) ?
C54 C45 N3 B2 . . . . -6.1(4) ?
C46 C45 N3 B2 . . . . 172.4(2) ?
C47 C48 N3 C45 . . . . 0.1(2) ?
C49 C48 N3 C45 . . . . 179.8(2) ?
C47 C48 N3 B2 . . . . -172.5(2) ?
C49 C48 N3 B2 . . . . 7.1(3) ?
F4 B2 N3 C45 . . . . -56.2(3) ?
F3 B2 N3 C45 . . . . 65.7(3) ?
N4 B2 N3 C45 . . . . -175.9(2) ?
F4 B2 N3 C48 . . . . 114.5(2) ?
F3 B2 N3 C48 . . . . -123.5(2) ?
N4 B2 N3 C48 . . . . -5.1(3) ?
C67 C53 N4 C50 . . . . 178.1(2) ?
C52 C53 N4 C50 . . . . -1.5(2) ?
C67 C53 N4 B2 . . . . -8.8(4) ?
C52 C53 N4 B2 . . . . 171.6(2) ?
C51 C50 N4 C53 . . . . 0.4(3) ?
C49 C50 N4 C53 . . . . 179.7(2) ?
C51 C50 N4 B2 . . . . -173.2(2) ?
C49 C50 N4 B2 . . . . 6.2(3) ?
F4 B2 N4 C53 . . . . 68.0(3) ?
F3 B2 N4 C53 . . . . -54.4(3) ?
N3 B2 N4 C53 . . . . -173.4(2) ?
F4 B2 N4 C50 . . . . -120.0(2) ?
F3 B2 N4 C50 . . . . 117.6(2) ?
N3 B2 N4 C50 . . . . -1.4(3) ?


####################################################################### 
# 
# 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_02687JorgeLabella
_database_code_depnum_ccdc_archive 'CCDC 1985335'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles'
;Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            JL364-68.MOR_200K
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H38 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         674.80

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   20.361(6)
_cell_length_b                   16.095(5)
_cell_length_c                   23.355(7)
_cell_angle_alpha                90
_cell_angle_beta                 114.048(7)
_cell_angle_gamma                90
_cell_volume                     6989.(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    735
_cell_measurement_theta_min      2.5310
_cell_measurement_theta_max      18.4944
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'dark purple'
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.028
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2848

_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.6197
_exptl_absorpt_correction_T_max  0.7449

_exptl_special_details           
;
;

_diffrn_ambient_temperature      200.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            35933
_diffrn_reflns_av_R_equivalents  0.2722
_diffrn_reflns_av_unetI/netI     0.2024
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         23.35
_diffrn_reflns_theta_full        23.35
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26

_refine_special_details          
;
;

_reflns_number_total             5058
_reflns_number_gt                1998
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.2306
_refine_ls_R_factor_gt           0.0729
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.2629
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_number_reflns         5058
_refine_ls_number_parameters     474
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1170P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.389
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2846(4) 0.4266(4) 0.5740(3) 0.0379(18) Uani d . . . 1 . .
C C2 0.3219(4) 0.4249(4) 0.5348(3) 0.0365(18) Uani d . . . 1 . .
C C3 0.3909(4) 0.3900(4) 0.5489(3) 0.0394(19) Uani d . . . 1 . .
H H3 0.4205 0.3613 0.5861 0.047 Uiso calc U . R 1 . .
C C4 0.4062(4) 0.4065(4) 0.4974(3) 0.0348(18) Uani d . . . 1 . .
C C5 0.3445(4) 0.4472(4) 0.4524(3) 0.0355(18) Uani d . . . 1 . .
C C6 0.4690(4) 0.3910(4) 0.4852(3) 0.0396(19) Uani d . . . 1 . .
C C7 0.5346(4) 0.3639(5) 0.5305(4) 0.048(2) Uani d . . . 1 . .
H H7 0.5388 0.351 0.5715 0.058 Uiso calc U . R 1 . .
C C8 0.5939(4) 0.3556(5) 0.5157(4) 0.053(2) Uani d . . . 1 . .
H H8 0.6391 0.3397 0.5473 0.064 Uiso calc U . R 1 . .
C C9 0.5872(5) 0.3705(5) 0.4553(4) 0.055(2) Uani d . . . 1 . .
H H9 0.6274 0.3627 0.4452 0.066 Uiso calc U . R 1 . .
C C10 0.5228(4) 0.3966(5) 0.4097(4) 0.054(2) Uani d . . . 1 . .
H H10 0.5186 0.4052 0.3681 0.065 Uiso calc U . R 1 . .
C C11 0.4631(4) 0.4106(4) 0.4241(4) 0.046(2) Uani d . . . 1 . .
C C12 0.3981(4) 0.4457(4) 0.3794(3) 0.043(2) Uani d . . . 1 . .
H H12 0.3951 0.4544 0.3382 0.052 Uiso calc U . R 1 . .
C C13 0.3395(4) 0.4680(4) 0.3907(3) 0.0364(18) Uani d . . . 1 . .
C C14 0.2792(4) 0.5148(5) 0.3443(3) 0.0385(19) Uani d . . . 1 . .
C C15 0.2933(4) 0.5739(5) 0.3069(3) 0.052(2) Uani d . . . 1 . .
H H15 0.3419 0.5839 0.3139 0.062 Uiso calc U . R 1 . .
C C16 0.2402(4) 0.6184(5) 0.2602(3) 0.051(2) Uani d . . . 1 . .
H H16 0.2518 0.6571 0.235 0.061 Uiso calc U . R 1 . .
C C17 0.1704(4) 0.6050(5) 0.2514(3) 0.048(2) Uani d . . . 1 . .
C C18 0.1527(4) 0.5469(5) 0.2875(3) 0.051(2) Uani d . . . 1 . .
H H18 0.1039 0.5373 0.2803 0.061 Uiso calc U . R 1 . .
C C19 0.2072(4) 0.5040(5) 0.3335(3) 0.0428(19) Uani d . . . 1 . .
H H19 0.1953 0.4657 0.3588 0.051 Uiso calc U . R 1 . .
C C20 0.1282(4) 0.7119(5) 0.1708(4) 0.064(2) Uani d . . . 1 . .
H H20A 0.163 0.7506 0.2 0.096 Uiso calc U . R 1 . .
H H20B 0.0839 0.7419 0.1456 0.096 Uiso calc U . R 1 . .
H H20C 0.1486 0.6877 0.1431 0.096 Uiso calc U . R 1 . .
C C21 0.2211(4) 0.4729(4) 0.5596(3) 0.0361(18) Uani d . . . 1 . .
C C22 0.1740(4) 0.4767(4) 0.5899(3) 0.0380(18) Uani d . . . 1 . .
H H22 0.1777 0.4451 0.6255 0.046 Uiso calc U . R 1 . .
C C23 0.1209(4) 0.5348(4) 0.5584(3) 0.0373(18) Uani d . . . 1 . .
C C24 0.1369(4) 0.5662(4) 0.5092(3) 0.0356(18) Uani d . . . 1 . .
C C25 0.0572(4) 0.5628(4) 0.5660(3) 0.0391(19) Uani d . . . 1 . .
C C26 0.0334(4) 0.5295(5) 0.6102(3) 0.047(2) Uani d . . . 1 . .
H H26 0.0598 0.4862 0.6375 0.057 Uiso calc U . R 1 . .
C C27 -0.0282(4) 0.5600(5) 0.6139(4) 0.051(2) Uani d . . . 1 . .
H H27 -0.044 0.5374 0.6437 0.062 Uiso calc U . R 1 . .
C C28 -0.0666(4) 0.6226(5) 0.5748(4) 0.053(2) Uani d . . . 1 . .
H H28 -0.1083 0.6435 0.5786 0.064 Uiso calc U . R 1 . .
C C29 -0.0463(4) 0.6556(5) 0.5306(3) 0.050(2) Uani d . . . 1 . .
H H29 -0.0738 0.6989 0.5039 0.059 Uiso calc U . R 1 . .
C C30 0.0163(4) 0.6250(5) 0.5246(3) 0.0409(19) Uani d . . . 1 . .
C C31 0.0383(4) 0.6586(5) 0.4780(3) 0.042(2) Uani d . . . 1 . .
H H31 0.0108 0.7028 0.4524 0.051 Uiso calc U . R 1 . .
C C32 0.0970(4) 0.6301(4) 0.4684(3) 0.0367(18) Uani d . . . 1 . .
C C33 0.1205(4) 0.6704(4) 0.4222(3) 0.0369(18) Uani d . . . 1 . .
C C34 0.0713(4) 0.6937(5) 0.3632(3) 0.049(2) Uani d . . . 1 . .
H H34 0.0222 0.6787 0.3496 0.058 Uiso calc U . R 1 . .
C C35 0.0939(5) 0.7387(5) 0.3241(3) 0.052(2) Uani d . . . 1 . .
H H35 0.0597 0.7545 0.2838 0.062 Uiso calc U . R 1 . .
C C36 0.1643(5) 0.7613(5) 0.3422(4) 0.050(2) Uani d . . . 1 . .
C C37 0.2140(4) 0.7371(5) 0.4001(4) 0.050(2) Uani d . . . 1 . .
H H37 0.2632 0.7515 0.4132 0.059 Uiso calc U . R 1 . .
C C38 0.1914(4) 0.6915(4) 0.4389(3) 0.044(2) Uani d . . . 1 . .
H H38 0.2261 0.6741 0.4785 0.053 Uiso calc U . R 1 . .
C C39 0.2533(5) 0.8335(6) 0.3169(4) 0.085(3) Uani d . . . 1 . .
H H39A 0.2683 0.8704 0.3534 0.127 Uiso calc U . R 1 . .
H H39B 0.257 0.8631 0.2816 0.127 Uiso calc U . R 1 . .
H H39C 0.2844 0.7844 0.3272 0.127 Uiso calc U . R 1 . .
C C40 0.3172(4) 0.3761(5) 0.6330(3) 0.0348(18) Uani d . . . 1 . .
C C41 0.2991(4) 0.2918(5) 0.6333(3) 0.0407(19) Uani d . . . 1 . .
C C42 0.3376(5) 0.2452(5) 0.6874(4) 0.054(2) Uani d . . . 1 . .
H H42 0.3259 0.1881 0.6876 0.064 Uiso calc U . R 1 . .
C C43 0.3907(5) 0.2772(6) 0.7395(4) 0.052(2) Uani d . . . 1 . .
C C44 0.4066(4) 0.3610(6) 0.7388(3) 0.050(2) Uani d . . . 1 . .
H H44 0.443 0.3852 0.7749 0.06 Uiso calc U . R 1 . .
C C45 0.3706(4) 0.4100(5) 0.6866(3) 0.0396(19) Uani d . . . 1 . .
C C46 0.2414(4) 0.2522(5) 0.5774(3) 0.057(2) Uani d . . . 1 . .
H H46A 0.2135 0.2954 0.5479 0.086 Uiso calc U . R 1 . .
H H46B 0.2095 0.2198 0.5909 0.086 Uiso calc U . R 1 . .
H H46C 0.2633 0.2154 0.5567 0.086 Uiso calc U . R 1 . .
C C47 0.4333(5) 0.2248(6) 0.7958(4) 0.093(3) Uani d . . . 1 . .
H H47A 0.4227 0.1659 0.7853 0.14 Uiso calc U . R 1 . .
H H47B 0.4202 0.2395 0.8305 0.14 Uiso calc U . R 1 . .
H H47C 0.4848 0.2348 0.8083 0.14 Uiso calc U . R 1 . .
C C48 0.3893(4) 0.5005(5) 0.6891(4) 0.067(3) Uani d . . . 1 . .
H H48A 0.4383 0.5093 0.7208 0.101 Uiso calc U . R 1 . .
H H48B 0.3555 0.533 0.7002 0.101 Uiso calc U . R 1 . .
H H48C 0.3864 0.5183 0.6481 0.101 Uiso calc U . R 1 . .
N N1 0.2947(3) 0.4605(3) 0.4750(2) 0.0334(14) Uani d . . . 1 . .
H H1N 0.2533 0.4862 0.4561 0.04 Uiso calc U P R 0.5 . .
N N2 0.1965(3) 0.5283(3) 0.5095(2) 0.0371(15) Uani d . . . 1 . .
H H2N 0.2161 0.5371 0.4827 0.045 Uiso calc U P R 0.5 . .
O O1 0.1121(3) 0.6461(3) 0.2059(2) 0.0598(15) Uani d . . . 1 . .
O O2 0.1802(3) 0.8082(3) 0.2999(2) 0.0616(16) Uani d . . . 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C21 . 1.409(9) ?
C1 C2 . 1.409(9) ?
C1 C40 . 1.501(9) ?
C2 N1 . 1.399(8) ?
C2 C3 . 1.421(9) ?
C3 C4 . 1.386(9) ?
C3 H3 . 0.95 ?
C4 C5 . 1.427(9) ?
C4 C6 . 1.439(9) ?
C5 N1 . 1.337(8) ?
C5 C13 . 1.443(9) ?
C6 C7 . 1.393(9) ?
C6 C11 . 1.420(10) ?
C7 C8 . 1.391(9) ?
C7 H7 . 0.95 ?
C8 C9 . 1.383(10) ?
C8 H8 . 0.95 ?
C9 C10 . 1.375(10) ?
C9 H9 . 0.95 ?
C10 C11 . 1.403(10) ?
C10 H10 . 0.95 ?
C11 C12 . 1.427(10) ?
C12 C13 . 1.370(9) ?
C12 H12 . 0.95 ?
C13 C14 . 1.472(9) ?
C14 C19 . 1.393(9) ?
C14 C15 . 1.399(10) ?
C15 C16 . 1.382(10) ?
C15 H15 . 0.95 ?
C16 C17 . 1.369(10) ?
C16 H16 . 0.95 ?
C17 O1 . 1.395(8) ?
C17 C18 . 1.401(10) ?
C18 C19 . 1.376(10) ?
C18 H18 . 0.95 ?
C19 H19 . 0.95 ?
C20 O1 . 1.457(8) ?
C20 H20A . 0.98 ?
C20 H20B . 0.98 ?
C20 H20C . 0.98 ?
C21 N2 . 1.392(8) ?
C21 C22 . 1.407(9) ?
C22 C23 . 1.391(9) ?
C22 H22 . 0.95 ?
C23 C24 . 1.409(9) ?
C23 C25 . 1.450(9) ?
C24 N2 . 1.357(8) ?
C24 C32 . 1.413(9) ?
C25 C30 . 1.404(10) ?
C25 C26 . 1.414(9) ?
C26 C27 . 1.382(9) ?
C26 H26 . 0.95 ?
C27 C28 . 1.371(10) ?
C27 H27 . 0.95 ?
C28 C29 . 1.367(10) ?
C28 H28 . 0.95 ?
C29 C30 . 1.426(9) ?
C29 H29 . 0.95 ?
C30 C31 . 1.442(9) ?
C31 C32 . 1.381(9) ?
C31 H31 . 0.95 ?
C32 C33 . 1.494(9) ?
C33 C38 . 1.375(9) ?
C33 C34 . 1.385(9) ?
C34 C35 . 1.382(10) ?
C34 H34 . 0.95 ?
C35 C36 . 1.368(10) ?
C35 H35 . 0.95 ?
C36 C37 . 1.374(10) ?
C36 O2 . 1.383(9) ?
C37 C38 . 1.383(9) ?
C37 H37 . 0.95 ?
C38 H38 . 0.95 ?
C39 O2 . 1.435(9) ?
C39 H39A . 0.98 ?
C39 H39B . 0.98 ?
C39 H39C . 0.98 ?
C40 C45 . 1.392(9) ?
C40 C41 . 1.406(9) ?
C41 C42 . 1.403(10) ?
C41 C46 . 1.498(9) ?
C42 C43 . 1.357(10) ?
C42 H42 . 0.95 ?
C43 C44 . 1.388(10) ?
C43 C47 . 1.505(10) ?
C44 C45 . 1.383(10) ?
C44 H44 . 0.95 ?
C45 C48 . 1.502(10) ?
C46 H46A . 0.98 ?
C46 H46B . 0.98 ?
C46 H46C . 0.98 ?
C47 H47A . 0.98 ?
C47 H47B . 0.98 ?
C47 H47C . 0.98 ?
C48 H48A . 0.98 ?
C48 H48B . 0.98 ?
C48 H48C . 0.98 ?
N1 H1N . 0.88 ?
N2 H2N . 0.88 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C21 C1 C2 . . 122.7(6) ?
C21 C1 C40 . . 121.7(6) ?
C2 C1 C40 . . 115.6(6) ?
N1 C2 C1 . . 122.9(6) ?
N1 C2 C3 . . 110.2(5) ?
C1 C2 C3 . . 126.9(6) ?
C4 C3 C2 . . 105.9(6) ?
C4 C3 H3 . . 127.1 ?
C2 C3 H3 . . 127.1 ?
C3 C4 C5 . . 106.6(6) ?
C3 C4 C6 . . 132.1(7) ?
C5 C4 C6 . . 121.3(6) ?
N1 C5 C4 . . 111.3(6) ?
N1 C5 C13 . . 126.9(6) ?
C4 C5 C13 . . 121.7(6) ?
C7 C6 C11 . . 119.6(7) ?
C7 C6 C4 . . 123.9(7) ?
C11 C6 C4 . . 116.4(7) ?
C8 C7 C6 . . 120.3(7) ?
C8 C7 H7 . . 119.9 ?
C6 C7 H7 . . 119.9 ?
C9 C8 C7 . . 120.1(7) ?
C9 C8 H8 . . 120.0 ?
C7 C8 H8 . . 120.0 ?
C10 C9 C8 . . 120.6(7) ?
C10 C9 H9 . . 119.7 ?
C8 C9 H9 . . 119.7 ?
C9 C10 C11 . . 120.6(8) ?
C9 C10 H10 . . 119.7 ?
C11 C10 H10 . . 119.7 ?
C10 C11 C6 . . 118.6(7) ?
C10 C11 C12 . . 121.7(7) ?
C6 C11 C12 . . 119.7(6) ?
C13 C12 C11 . . 125.8(6) ?
C13 C12 H12 . . 117.1 ?
C11 C12 H12 . . 117.1 ?
C12 C13 C5 . . 114.8(6) ?
C12 C13 C14 . . 121.6(6) ?
C5 C13 C14 . . 123.5(6) ?
C19 C14 C15 . . 116.2(7) ?
C19 C14 C13 . . 124.8(6) ?
C15 C14 C13 . . 119.1(6) ?
C16 C15 C14 . . 123.5(7) ?
C16 C15 H15 . . 118.3 ?
C14 C15 H15 . . 118.3 ?
C17 C16 C15 . . 117.9(7) ?
C17 C16 H16 . . 121.1 ?
C15 C16 H16 . . 121.1 ?
C16 C17 O1 . . 123.2(7) ?
C16 C17 C18 . . 121.4(7) ?
O1 C17 C18 . . 115.3(7) ?
C19 C18 C17 . . 118.8(7) ?
C19 C18 H18 . . 120.6 ?
C17 C18 H18 . . 120.6 ?
C18 C19 C14 . . 122.2(7) ?
C18 C19 H19 . . 118.9 ?
C14 C19 H19 . . 118.9 ?
O1 C20 H20A . . 109.5 ?
O1 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
O1 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
N2 C21 C22 . . 108.1(6) ?
N2 C21 C1 . . 121.4(6) ?
C22 C21 C1 . . 130.5(7) ?
C23 C22 C21 . . 107.8(6) ?
C23 C22 H22 . . 126.1 ?
C21 C22 H22 . . 126.1 ?
C22 C23 C24 . . 106.6(6) ?
C22 C23 C25 . . 133.2(7) ?
C24 C23 C25 . . 120.1(7) ?
N2 C24 C23 . . 109.8(6) ?
N2 C24 C32 . . 126.7(6) ?
C23 C24 C32 . . 123.5(7) ?
C30 C25 C26 . . 119.2(7) ?
C30 C25 C23 . . 116.6(6) ?
C26 C25 C23 . . 124.1(7) ?
C27 C26 C25 . . 120.1(7) ?
C27 C26 H26 . . 120.0 ?
C25 C26 H26 . . 120.0 ?
C28 C27 C26 . . 120.4(8) ?
C28 C27 H27 . . 119.8 ?
C26 C27 H27 . . 119.8 ?
C29 C28 C27 . . 121.5(7) ?
C29 C28 H28 . . 119.2 ?
C27 C28 H28 . . 119.2 ?
C28 C29 C30 . . 119.8(7) ?
C28 C29 H29 . . 120.1 ?
C30 C29 H29 . . 120.1 ?
C25 C30 C29 . . 118.9(7) ?
C25 C30 C31 . . 120.5(6) ?
C29 C30 C31 . . 120.6(7) ?
C32 C31 C30 . . 123.6(7) ?
C32 C31 H31 . . 118.2 ?
C30 C31 H31 . . 118.2 ?
C31 C32 C24 . . 115.4(7) ?
C31 C32 C33 . . 121.8(6) ?
C24 C32 C33 . . 122.5(6) ?
C38 C33 C34 . . 117.7(7) ?
C38 C33 C32 . . 120.7(6) ?
C34 C33 C32 . . 121.4(7) ?
C35 C34 C33 . . 119.9(7) ?
C35 C34 H34 . . 120.0 ?
C33 C34 H34 . . 120.0 ?
C36 C35 C34 . . 121.6(7) ?
C36 C35 H35 . . 119.2 ?
C34 C35 H35 . . 119.2 ?
C35 C36 C37 . . 119.2(7) ?
C35 C36 O2 . . 116.4(7) ?
C37 C36 O2 . . 124.4(8) ?
C36 C37 C38 . . 119.1(7) ?
C36 C37 H37 . . 120.4 ?
C38 C37 H37 . . 120.4 ?
C33 C38 C37 . . 122.4(7) ?
C33 C38 H38 . . 118.8 ?
C37 C38 H38 . . 118.8 ?
O2 C39 H39A . . 109.5 ?
O2 C39 H39B . . 109.5 ?
H39A C39 H39B . . 109.5 ?
O2 C39 H39C . . 109.5 ?
H39A C39 H39C . . 109.5 ?
H39B C39 H39C . . 109.5 ?
C45 C40 C41 . . 118.9(6) ?
C45 C40 C1 . . 120.3(7) ?
C41 C40 C1 . . 120.5(6) ?
C42 C41 C40 . . 117.9(7) ?
C42 C41 C46 . . 120.6(7) ?
C40 C41 C46 . . 121.4(7) ?
C43 C42 C41 . . 123.6(8) ?
C43 C42 H42 . . 118.2 ?
C41 C42 H42 . . 118.2 ?
C42 C43 C44 . . 117.5(7) ?
C42 C43 C47 . . 122.4(9) ?
C44 C43 C47 . . 120.1(8) ?
C45 C44 C43 . . 121.5(8) ?
C45 C44 H44 . . 119.3 ?
C43 C44 H44 . . 119.3 ?
C44 C45 C40 . . 120.5(7) ?
C44 C45 C48 . . 118.9(7) ?
C40 C45 C48 . . 120.5(7) ?
C41 C46 H46A . . 109.5 ?
C41 C46 H46B . . 109.5 ?
H46A C46 H46B . . 109.5 ?
C41 C46 H46C . . 109.5 ?
H46A C46 H46C . . 109.5 ?
H46B C46 H46C . . 109.5 ?
C43 C47 H47A . . 109.5 ?
C43 C47 H47B . . 109.5 ?
H47A C47 H47B . . 109.5 ?
C43 C47 H47C . . 109.5 ?
H47A C47 H47C . . 109.5 ?
H47B C47 H47C . . 109.5 ?
C45 C48 H48A . . 109.5 ?
C45 C48 H48B . . 109.5 ?
H48A C48 H48B . . 109.5 ?
C45 C48 H48C . . 109.5 ?
H48A C48 H48C . . 109.5 ?
H48B C48 H48C . . 109.5 ?
C5 N1 C2 . . 105.9(5) ?
C5 N1 H1N . . 127.1 ?
C2 N1 H1N . . 127.1 ?
C24 N2 C21 . . 107.8(5) ?
C24 N2 H2N . . 126.1 ?
C21 N2 H2N . . 126.1 ?
C17 O1 C20 . . 117.2(6) ?
C36 O2 C39 . . 118.4(6) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C21 C1 C2 N1 . . . . -8.2(11) ?
C40 C1 C2 N1 . . . . 172.4(6) ?
C21 C1 C2 C3 . . . . 170.6(7) ?
C40 C1 C2 C3 . . . . -8.8(10) ?
N1 C2 C3 C4 . . . . 1.4(8) ?
C1 C2 C3 C4 . . . . -177.5(7) ?
C2 C3 C4 C5 . . . . -2.8(8) ?
C2 C3 C4 C6 . . . . 176.1(7) ?
C3 C4 C5 N1 . . . . 3.5(8) ?
C6 C4 C5 N1 . . . . -175.6(6) ?
C3 C4 C5 C13 . . . . -175.2(6) ?
C6 C4 C5 C13 . . . . 5.7(10) ?
C3 C4 C6 C7 . . . . -9.5(12) ?
C5 C4 C6 C7 . . . . 169.4(7) ?
C3 C4 C6 C11 . . . . 174.9(7) ?
C5 C4 C6 C11 . . . . -6.2(10) ?
C11 C6 C7 C8 . . . . -0.3(11) ?
C4 C6 C7 C8 . . . . -175.8(7) ?
C6 C7 C8 C9 . . . . -3.1(11) ?
C7 C8 C9 C10 . . . . 2.4(12) ?
C8 C9 C10 C11 . . . . 1.7(12) ?
C9 C10 C11 C6 . . . . -5.0(11) ?
C9 C10 C11 C12 . . . . 173.5(7) ?
C7 C6 C11 C10 . . . . 4.3(10) ?
C4 C6 C11 C10 . . . . -179.9(7) ?
C7 C6 C11 C12 . . . . -174.2(7) ?
C4 C6 C11 C12 . . . . 1.6(10) ?
C10 C11 C12 C13 . . . . -174.2(7) ?
C6 C11 C12 C13 . . . . 4.2(11) ?
C11 C12 C13 C5 . . . . -4.9(10) ?
C11 C12 C13 C14 . . . . 170.9(7) ?
N1 C5 C13 C12 . . . . -178.6(7) ?
C4 C5 C13 C12 . . . . -0.1(10) ?
N1 C5 C13 C14 . . . . 5.7(11) ?
C4 C5 C13 C14 . . . . -175.8(7) ?
C12 C13 C14 C19 . . . . 144.2(7) ?
C5 C13 C14 C19 . . . . -40.4(11) ?
C12 C13 C14 C15 . . . . -34.5(10) ?
C5 C13 C14 C15 . . . . 140.9(7) ?
C19 C14 C15 C16 . . . . -1.8(11) ?
C13 C14 C15 C16 . . . . 177.0(7) ?
C14 C15 C16 C17 . . . . 1.5(12) ?
C15 C16 C17 O1 . . . . 179.9(6) ?
C15 C16 C17 C18 . . . . -1.3(11) ?
C16 C17 C18 C19 . . . . 1.4(11) ?
O1 C17 C18 C19 . . . . -179.8(6) ?
C17 C18 C19 C14 . . . . -1.7(11) ?
C15 C14 C19 C18 . . . . 1.9(10) ?
C13 C14 C19 C18 . . . . -176.9(7) ?
C2 C1 C21 N2 . . . . -8.2(10) ?
C40 C1 C21 N2 . . . . 171.2(6) ?
C2 C1 C21 C22 . . . . 174.1(7) ?
C40 C1 C21 C22 . . . . -6.5(12) ?
N2 C21 C22 C23 . . . . -0.4(7) ?
C1 C21 C22 C23 . . . . 177.5(7) ?
C21 C22 C23 C24 . . . . -0.3(7) ?
C21 C22 C23 C25 . . . . 177.2(7) ?
C22 C23 C24 N2 . . . . 0.9(8) ?
C25 C23 C24 N2 . . . . -176.9(6) ?
C22 C23 C24 C32 . . . . -176.7(6) ?
C25 C23 C24 C32 . . . . 5.4(10) ?
C22 C23 C25 C30 . . . . 179.2(7) ?
C24 C23 C25 C30 . . . . -3.6(9) ?
C22 C23 C25 C26 . . . . -3.1(12) ?
C24 C23 C25 C26 . . . . 174.1(7) ?
C30 C25 C26 C27 . . . . -2.1(10) ?
C23 C25 C26 C27 . . . . -179.8(7) ?
C25 C26 C27 C28 . . . . 0.0(11) ?
C26 C27 C28 C29 . . . . 1.2(11) ?
C27 C28 C29 C30 . . . . -0.2(11) ?
C26 C25 C30 C29 . . . . 3.1(10) ?
C23 C25 C30 C29 . . . . -179.1(6) ?
C26 C25 C30 C31 . . . . -178.4(6) ?
C23 C25 C30 C31 . . . . -0.6(9) ?
C28 C29 C30 C25 . . . . -2.0(10) ?
C28 C29 C30 C31 . . . . 179.5(6) ?
C25 C30 C31 C32 . . . . 3.6(10) ?
C29 C30 C31 C32 . . . . -178.0(6) ?
C30 C31 C32 C24 . . . . -2.0(10) ?
C30 C31 C32 C33 . . . . -176.1(6) ?
N2 C24 C32 C31 . . . . -179.7(6) ?
C23 C24 C32 C31 . . . . -2.5(9) ?
N2 C24 C32 C33 . . . . -5.7(10) ?
C23 C24 C32 C33 . . . . 171.5(6) ?
C31 C32 C33 C38 . . . . 131.1(7) ?
C24 C32 C33 C38 . . . . -42.6(9) ?
C31 C32 C33 C34 . . . . -43.6(10) ?
C24 C32 C33 C34 . . . . 142.7(7) ?
C38 C33 C34 C35 . . . . -1.9(10) ?
C32 C33 C34 C35 . . . . 173.0(6) ?
C33 C34 C35 C36 . . . . 0.1(11) ?
C34 C35 C36 C37 . . . . 1.3(12) ?
C34 C35 C36 O2 . . . . -178.3(7) ?
C35 C36 C37 C38 . . . . -0.8(11) ?
O2 C36 C37 C38 . . . . 178.8(7) ?
C34 C33 C38 C37 . . . . 2.4(10) ?
C32 C33 C38 C37 . . . . -172.5(7) ?
C36 C37 C38 C33 . . . . -1.1(11) ?
C21 C1 C40 C45 . . . . -93.6(8) ?
C2 C1 C40 C45 . . . . 85.8(8) ?
C21 C1 C40 C41 . . . . 92.3(8) ?
C2 C1 C40 C41 . . . . -88.3(8) ?
C45 C40 C41 C42 . . . . -1.8(9) ?
C1 C40 C41 C42 . . . . 172.4(6) ?
C45 C40 C41 C46 . . . . 179.1(6) ?
C1 C40 C41 C46 . . . . -6.8(10) ?
C40 C41 C42 C43 . . . . 0.6(11) ?
C46 C41 C42 C43 . . . . 179.7(7) ?
C41 C42 C43 C44 . . . . 0.8(12) ?
C41 C42 C43 C47 . . . . -177.2(7) ?
C42 C43 C44 C45 . . . . -1.0(11) ?
C47 C43 C44 C45 . . . . 177.1(7) ?
C43 C44 C45 C40 . . . . -0.3(10) ?
C43 C44 C45 C48 . . . . 178.9(7) ?
C41 C40 C45 C44 . . . . 1.7(10) ?
C1 C40 C45 C44 . . . . -172.5(6) ?
C41 C40 C45 C48 . . . . -177.5(6) ?
C1 C40 C45 C48 . . . . 8.3(10) ?
C4 C5 N1 C2 . . . . -2.6(7) ?
C13 C5 N1 C2 . . . . 176.1(6) ?
C1 C2 N1 C5 . . . . 179.7(6) ?
C3 C2 N1 C5 . . . . 0.7(7) ?
C23 C24 N2 C21 . . . . -1.2(7) ?
C32 C24 N2 C21 . . . . 176.3(6) ?
C22 C21 N2 C24 . . . . 1.0(7) ?
C1 C21 N2 C24 . . . . -177.1(6) ?
C16 C17 O1 C20 . . . . -6.2(10) ?
C18 C17 O1 C20 . . . . 175.0(6) ?
C35 C36 O2 C39 . . . . 179.8(7) ?
C37 C36 O2 C39 . . . . 0.2(11) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C20 H20A O2 . 0.98 2.40 3.164(10) 134.5 ?
N1 H1N N2 . 0.88 2.13 2.674(8) 119.6 ?
N2 H2N N1 . 0.88 2.09 2.674(8) 123.5 ?


####################################################################### 
# 
# 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_02815JorgeLabella
_database_code_depnum_ccdc_archive 'CCDC 1985332'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles'
;Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            JL376-11
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H29 B F2 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         538.42

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.1937(6)
_cell_length_b                   11.0010(6)
_cell_length_c                   14.2800(7)
_cell_angle_alpha                105.446(3)
_cell_angle_beta                 103.611(3)
_cell_angle_gamma                94.765(3)
_cell_volume                     1481.92(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1964
_cell_measurement_theta_min      2.8115
_cell_measurement_theta_max      20.3272
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.071
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             564

_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            21050
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_av_unetI/netI     0.0957
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             5433
_reflns_number_gt                2660
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1582
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_gt          0.1473
_refine_ls_wR_factor_ref         0.2279
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_number_reflns         5433
_refine_ls_number_parameters     375
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1180P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.487
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.3264(4) 0.7310(4) 0.2789(3) 0.0434(10) Uani d . . . 1 . .
C C1 0.4357(3) 0.9688(3) 0.3286(3) 0.0465(9) Uani d . . . 1 . .
C C2 0.5595(4) 1.0436(4) 0.3895(3) 0.0599(11) Uani d . . . 1 . .
H H2 0.5809 1.1317 0.4045 0.072 Uiso calc U . R 1 . .
C C3 0.6433(4) 0.9652(4) 0.4229(3) 0.0538(10) Uani d . . . 1 . .
H H3 0.7315 0.9901 0.4654 0.065 Uiso calc U . R 1 . .
C C4 0.5722(3) 0.8398(3) 0.3814(2) 0.0417(9) Uani d . . . 1 . .
C C5 0.6154(3) 0.7230(3) 0.3790(2) 0.0379(8) Uani d . . . 1 . .
C C6 0.5297(3) 0.6100(3) 0.3198(2) 0.0390(8) Uani d . . . 1 . .
C C7 0.5582(4) 0.4852(3) 0.2905(3) 0.0464(9) Uani d . . . 1 . .
H H7 0.6407 0.4582 0.3132 0.056 Uiso calc U . R 1 . .
C C8 0.4435(3) 0.4100(3) 0.2227(3) 0.0469(9) Uani d . . . 1 . .
H H8 0.4346 0.3232 0.1902 0.056 Uiso calc U . R 1 . .
C C9 0.3420(3) 0.4869(3) 0.2112(2) 0.0385(8) Uani d . . . 1 . .
C C10 0.3158(4) 1.0097(3) 0.2704(3) 0.0487(9) Uani d . . . 1 . .
C C11 0.1899(4) 0.9997(4) 0.2914(3) 0.0637(11) Uani d . . . 1 . .
H H11 0.18 0.9665 0.3432 0.076 Uiso calc U . R 1 . .
C C12 0.0799(4) 1.0379(4) 0.2373(4) 0.0722(13) Uani d . . . 1 . .
H H12 -0.0033 1.0324 0.2534 0.087 Uiso calc U . R 1 . .
C C13 0.0930(5) 1.0842(4) 0.1593(4) 0.0727(13) Uani d . . . 1 . .
H H13 0.0182 1.1096 0.122 0.087 Uiso calc U . R 1 . .
C C14 0.2154(4) 1.0934(4) 0.1361(3) 0.0659(12) Uani d . . . 1 . .
H H14 0.2227 1.1243 0.0826 0.079 Uiso calc U . R 1 . .
C C15 0.3288(4) 1.0574(3) 0.1909(3) 0.0519(10) Uani d . . . 1 . .
C C16 0.4564(5) 1.0663(4) 0.1651(3) 0.0605(11) Uani d . . . 1 . .
C C17 0.5599(5) 1.0747(5) 0.1430(3) 0.0750(13) Uani d . . . 1 . .
C C18 0.6910(5) 1.0819(7) 0.1155(4) 0.130(2) Uani d . . . 1 . .
H H18A 0.7472 1.1622 0.1544 0.195 Uiso calc U . R 1 . .
H H18B 0.6735 1.0747 0.045 0.195 Uiso calc U . R 1 . .
H H18C 0.7372 1.0135 0.1292 0.195 Uiso calc U . R 1 . .
C C19 0.1981(3) 0.4454(3) 0.1516(3) 0.0414(9) Uani d . . . 1 . .
C C20 0.0924(4) 0.4725(3) 0.1954(3) 0.0505(10) Uani d . . . 1 . .
H H20 0.1122 0.5213 0.2625 0.061 Uiso calc U . R 1 . .
C C21 -0.0421(4) 0.4282(4) 0.1409(4) 0.0638(11) Uani d . . . 1 . .
H H21 -0.1122 0.4475 0.1713 0.077 Uiso calc U . R 1 . .
C C22 -0.0722(4) 0.3554(4) 0.0415(3) 0.0662(12) Uani d . . . 1 . .
H H22 -0.1627 0.3251 0.005 0.079 Uiso calc U . R 1 . .
C C23 0.0300(4) 0.3274(4) -0.0038(3) 0.0597(11) Uani d . . . 1 . .
H H23 0.0084 0.2786 -0.071 0.072 Uiso calc U . R 1 . .
C C24 0.1666(4) 0.3712(3) 0.0498(3) 0.0462(9) Uani d . . . 1 . .
C C25 0.2734(4) 0.3438(4) 0.0015(3) 0.0543(10) Uani d . . . 1 . .
C C26 0.3647(5) 0.3236(4) -0.0354(3) 0.0661(12) Uani d . . . 1 . .
C C27 0.4811(5) 0.3001(6) -0.0780(4) 0.1040(18) Uani d . . . 1 . .
H H27A 0.5144 0.3752 -0.0927 0.156 Uiso calc U . R 1 . .
H H27B 0.4526 0.2301 -0.1389 0.156 Uiso calc U . R 1 . .
H H27C 0.5526 0.2797 -0.0302 0.156 Uiso calc U . R 1 . .
C C28 0.7561(3) 0.7158(3) 0.4352(2) 0.0399(8) Uani d . . . 1 . .
C C29 0.8676(4) 0.7368(4) 0.3977(3) 0.0530(10) Uani d . . . 1 . .
C C30 0.9955(4) 0.7237(4) 0.4514(3) 0.0647(12) Uani d . . . 1 . .
H H30 1.0703 0.7377 0.4268 0.078 Uiso calc U . R 1 . .
C C31 1.0159(4) 0.6908(4) 0.5397(3) 0.0556(10) Uani d . . . 1 . .
C C32 0.9044(4) 0.6708(4) 0.5745(3) 0.0535(10) Uani d . . . 1 . .
H H32 0.9168 0.6489 0.6342 0.064 Uiso calc U . R 1 . .
C C33 0.7740(3) 0.6818(3) 0.5248(2) 0.0427(9) Uani d . . . 1 . .
C C34 0.8517(5) 0.7686(5) 0.2992(3) 0.0894(16) Uani d . . . 1 . .
H H34A 0.9384 0.7734 0.2837 0.134 Uiso calc U . R 1 . .
H H34B 0.8199 0.8494 0.3052 0.134 Uiso calc U . R 1 . .
H H34C 0.7869 0.7034 0.2461 0.134 Uiso calc U . R 1 . .
C C35 1.1564(4) 0.6747(5) 0.5940(4) 0.0974(17) Uani d . . . 1 . .
H H35A 1.2 0.7531 0.6451 0.146 Uiso calc U . R 1 . .
H H35B 1.21 0.653 0.5467 0.146 Uiso calc U . R 1 . .
H H35C 1.1486 0.6077 0.6248 0.146 Uiso calc U . R 1 . .
C C36 0.6569(4) 0.6563(4) 0.5675(3) 0.0633(11) Uani d . . . 1 . .
H H36A 0.6192 0.5673 0.5412 0.095 Uiso calc U . R 1 . .
H H36B 0.5878 0.7062 0.5489 0.095 Uiso calc U . R 1 . .
H H36C 0.6889 0.6792 0.6397 0.095 Uiso calc U . R 1 . .
F F1 0.2514(2) 0.7314(2) 0.18584(17) 0.0702(7) Uani d . . . 1 . .
F F2 0.2453(2) 0.7371(2) 0.34451(19) 0.0771(7) Uani d . . . 1 . .
N N1 0.4429(2) 0.8456(3) 0.32453(19) 0.0393(7) Uani d . . . 1 . .
N N2 0.3936(2) 0.6085(3) 0.26926(19) 0.0359(7) Uani d . . . 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 F1 . 1.370(4) ?
B1 F2 . 1.380(4) ?
B1 N1 . 1.542(5) ?
B1 N2 . 1.551(5) ?
C1 N1 . 1.349(4) ?
C1 C2 . 1.399(5) ?
C1 C10 . 1.483(5) ?
C2 C3 . 1.360(5) ?
C2 H2 . 0.93 ?
C3 C4 . 1.406(5) ?
C3 H3 . 0.93 ?
C4 C5 . 1.387(5) ?
C4 N1 . 1.392(4) ?
C5 C6 . 1.391(5) ?
C5 C28 . 1.489(4) ?
C6 C7 . 1.400(5) ?
C6 N2 . 1.402(4) ?
C7 C8 . 1.367(5) ?
C7 H7 . 0.93 ?
C8 C9 . 1.397(4) ?
C8 H8 . 0.93 ?
C9 N2 . 1.357(4) ?
C9 C19 . 1.476(5) ?
C10 C11 . 1.387(5) ?
C10 C15 . 1.400(5) ?
C11 C12 . 1.369(5) ?
C11 H11 . 0.93 ?
C12 C13 . 1.371(6) ?
C12 H12 . 0.93 ?
C13 C14 . 1.367(6) ?
C13 H13 . 0.93 ?
C14 C15 . 1.386(5) ?
C14 H14 . 0.93 ?
C15 C16 . 1.435(6) ?
C16 C17 . 1.175(5) ?
C17 C18 . 1.480(7) ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
C19 C20 . 1.382(5) ?
C19 C24 . 1.410(5) ?
C20 C21 . 1.381(5) ?
C20 H20 . 0.93 ?
C21 C22 . 1.378(6) ?
C21 H21 . 0.93 ?
C22 C23 . 1.365(5) ?
C22 H22 . 0.93 ?
C23 C24 . 1.395(5) ?
C23 H23 . 0.93 ?
C24 C25 . 1.432(5) ?
C25 C26 . 1.181(5) ?
C26 C27 . 1.467(6) ?
C27 H27A . 0.96 ?
C27 H27B . 0.96 ?
C27 H27C . 0.96 ?
C28 C29 . 1.393(5) ?
C28 C33 . 1.403(4) ?
C29 C30 . 1.389(5) ?
C29 C34 . 1.514(5) ?
C30 C31 . 1.377(5) ?
C30 H30 . 0.93 ?
C31 C32 . 1.367(5) ?
C31 C35 . 1.509(5) ?
C32 C33 . 1.383(5) ?
C32 H32 . 0.93 ?
C33 C36 . 1.501(5) ?
C34 H34A . 0.96 ?
C34 H34B . 0.96 ?
C34 H34C . 0.96 ?
C35 H35A . 0.96 ?
C35 H35B . 0.96 ?
C35 H35C . 0.96 ?
C36 H36A . 0.96 ?
C36 H36B . 0.96 ?
C36 H36C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 B1 F2 . . 110.9(3) ?
F1 B1 N1 . . 110.9(3) ?
F2 B1 N1 . . 108.3(3) ?
F1 B1 N2 . . 109.8(3) ?
F2 B1 N2 . . 109.7(3) ?
N1 B1 N2 . . 107.0(3) ?
N1 C1 C2 . . 108.8(3) ?
N1 C1 C10 . . 122.9(3) ?
C2 C1 C10 . . 128.2(3) ?
C3 C2 C1 . . 108.2(3) ?
C3 C2 H2 . . 125.9 ?
C1 C2 H2 . . 125.9 ?
C2 C3 C4 . . 107.5(3) ?
C2 C3 H3 . . 126.3 ?
C4 C3 H3 . . 126.3 ?
C5 C4 N1 . . 120.6(3) ?
C5 C4 C3 . . 131.3(3) ?
N1 C4 C3 . . 107.5(3) ?
C4 C5 C6 . . 120.3(3) ?
C4 C5 C28 . . 121.0(3) ?
C6 C5 C28 . . 118.6(3) ?
C5 C6 C7 . . 130.3(3) ?
C5 C6 N2 . . 121.9(3) ?
C7 C6 N2 . . 107.4(3) ?
C8 C7 C6 . . 108.1(3) ?
C8 C7 H7 . . 126.0 ?
C6 C7 H7 . . 126.0 ?
C7 C8 C9 . . 107.7(3) ?
C7 C8 H8 . . 126.1 ?
C9 C8 H8 . . 126.1 ?
N2 C9 C8 . . 109.2(3) ?
N2 C9 C19 . . 123.6(3) ?
C8 C9 C19 . . 127.1(3) ?
C11 C10 C15 . . 118.9(3) ?
C11 C10 C1 . . 121.8(3) ?
C15 C10 C1 . . 119.3(3) ?
C12 C11 C10 . . 121.3(4) ?
C12 C11 H11 . . 119.4 ?
C10 C11 H11 . . 119.4 ?
C11 C12 C13 . . 119.6(4) ?
C11 C12 H12 . . 120.2 ?
C13 C12 H12 . . 120.2 ?
C14 C13 C12 . . 120.3(4) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C13 C14 C15 . . 121.1(4) ?
C13 C14 H14 . . 119.5 ?
C15 C14 H14 . . 119.5 ?
C14 C15 C10 . . 118.8(4) ?
C14 C15 C16 . . 120.6(4) ?
C10 C15 C16 . . 120.6(3) ?
C17 C16 C15 . . 178.9(4) ?
C16 C17 C18 . . 178.4(5) ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C20 C19 C24 . . 118.9(3) ?
C20 C19 C9 . . 121.0(3) ?
C24 C19 C9 . . 120.0(3) ?
C21 C20 C19 . . 121.0(4) ?
C21 C20 H20 . . 119.5 ?
C19 C20 H20 . . 119.5 ?
C22 C21 C20 . . 119.8(4) ?
C22 C21 H21 . . 120.1 ?
C20 C21 H21 . . 120.1 ?
C23 C22 C21 . . 120.5(4) ?
C23 C22 H22 . . 119.8 ?
C21 C22 H22 . . 119.8 ?
C22 C23 C24 . . 120.6(4) ?
C22 C23 H23 . . 119.7 ?
C24 C23 H23 . . 119.7 ?
C23 C24 C19 . . 119.2(4) ?
C23 C24 C25 . . 120.5(3) ?
C19 C24 C25 . . 120.3(3) ?
C26 C25 C24 . . 177.7(4) ?
C25 C26 C27 . . 178.2(5) ?
C26 C27 H27A . . 109.5 ?
C26 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C26 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C29 C28 C33 . . 120.2(3) ?
C29 C28 C5 . . 121.0(3) ?
C33 C28 C5 . . 118.7(3) ?
C30 C29 C28 . . 118.3(3) ?
C30 C29 C34 . . 119.8(4) ?
C28 C29 C34 . . 121.8(3) ?
C31 C30 C29 . . 122.6(4) ?
C31 C30 H30 . . 118.7 ?
C29 C30 H30 . . 118.7 ?
C32 C31 C30 . . 117.7(3) ?
C32 C31 C35 . . 121.7(4) ?
C30 C31 C35 . . 120.6(4) ?
C31 C32 C33 . . 122.9(3) ?
C31 C32 H32 . . 118.6 ?
C33 C32 H32 . . 118.6 ?
C32 C33 C28 . . 118.3(3) ?
C32 C33 C36 . . 119.4(3) ?
C28 C33 C36 . . 122.3(3) ?
C29 C34 H34A . . 109.5 ?
C29 C34 H34B . . 109.5 ?
H34A C34 H34B . . 109.5 ?
C29 C34 H34C . . 109.5 ?
H34A C34 H34C . . 109.5 ?
H34B C34 H34C . . 109.5 ?
C31 C35 H35A . . 109.5 ?
C31 C35 H35B . . 109.5 ?
H35A C35 H35B . . 109.5 ?
C31 C35 H35C . . 109.5 ?
H35A C35 H35C . . 109.5 ?
H35B C35 H35C . . 109.5 ?
C33 C36 H36A . . 109.5 ?
C33 C36 H36B . . 109.5 ?
H36A C36 H36B . . 109.5 ?
C33 C36 H36C . . 109.5 ?
H36A C36 H36C . . 109.5 ?
H36B C36 H36C . . 109.5 ?
C1 N1 C4 . . 108.1(3) ?
C1 N1 B1 . . 127.8(3) ?
C4 N1 B1 . . 123.7(3) ?
C9 N2 C6 . . 107.6(3) ?
C9 N2 B1 . . 129.7(3) ?
C6 N2 B1 . . 122.6(3) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . 0.0(4) ?
C10 C1 C2 C3 . . . . -176.1(4) ?
C1 C2 C3 C4 . . . . 0.9(4) ?
C2 C3 C4 C5 . . . . 169.5(4) ?
C2 C3 C4 N1 . . . . -1.4(4) ?
N1 C4 C5 C6 . . . . -0.3(5) ?
C3 C4 C5 C6 . . . . -170.3(4) ?
N1 C4 C5 C28 . . . . 176.7(3) ?
C3 C4 C5 C28 . . . . 6.7(6) ?
C4 C5 C6 C7 . . . . 166.5(3) ?
C28 C5 C6 C7 . . . . -10.5(5) ?
C4 C5 C6 N2 . . . . -6.6(5) ?
C28 C5 C6 N2 . . . . 176.4(3) ?
C5 C6 C7 C8 . . . . -172.9(3) ?
N2 C6 C7 C8 . . . . 0.9(4) ?
C6 C7 C8 C9 . . . . -1.3(4) ?
C7 C8 C9 N2 . . . . 1.2(4) ?
C7 C8 C9 C19 . . . . -175.0(3) ?
N1 C1 C10 C11 . . . . 67.4(5) ?
C2 C1 C10 C11 . . . . -116.9(5) ?
N1 C1 C10 C15 . . . . -111.2(4) ?
C2 C1 C10 C15 . . . . 64.5(5) ?
C15 C10 C11 C12 . . . . -1.3(6) ?
C1 C10 C11 C12 . . . . 180.0(4) ?
C10 C11 C12 C13 . . . . 1.5(7) ?
C11 C12 C13 C14 . . . . -0.6(7) ?
C12 C13 C14 C15 . . . . -0.6(7) ?
C13 C14 C15 C10 . . . . 0.7(6) ?
C13 C14 C15 C16 . . . . 179.4(4) ?
C11 C10 C15 C14 . . . . 0.2(6) ?
C1 C10 C15 C14 . . . . 178.9(4) ?
C11 C10 C15 C16 . . . . -178.4(4) ?
C1 C10 C15 C16 . . . . 0.3(5) ?
N2 C9 C19 C20 . . . . -51.3(4) ?
C8 C9 C19 C20 . . . . 124.4(4) ?
N2 C9 C19 C24 . . . . 132.1(3) ?
C8 C9 C19 C24 . . . . -52.2(5) ?
C24 C19 C20 C21 . . . . -0.1(5) ?
C9 C19 C20 C21 . . . . -176.7(3) ?
C19 C20 C21 C22 . . . . 0.3(6) ?
C20 C21 C22 C23 . . . . -0.5(6) ?
C21 C22 C23 C24 . . . . 0.4(6) ?
C22 C23 C24 C19 . . . . -0.2(5) ?
C22 C23 C24 C25 . . . . -178.8(3) ?
C20 C19 C24 C23 . . . . 0.0(5) ?
C9 C19 C24 C23 . . . . 176.7(3) ?
C20 C19 C24 C25 . . . . 178.6(3) ?
C9 C19 C24 C25 . . . . -4.7(5) ?
C4 C5 C28 C29 . . . . -78.1(4) ?
C6 C5 C28 C29 . . . . 98.9(4) ?
C4 C5 C28 C33 . . . . 104.7(4) ?
C6 C5 C28 C33 . . . . -78.3(4) ?
C33 C28 C29 C30 . . . . -0.3(6) ?
C5 C28 C29 C30 . . . . -177.4(4) ?
C33 C28 C29 C34 . . . . 177.6(4) ?
C5 C28 C29 C34 . . . . 0.5(6) ?
C28 C29 C30 C31 . . . . 0.1(6) ?
C34 C29 C30 C31 . . . . -177.8(4) ?
C29 C30 C31 C32 . . . . -0.1(6) ?
C29 C30 C31 C35 . . . . 178.5(4) ?
C30 C31 C32 C33 . . . . 0.3(6) ?
C35 C31 C32 C33 . . . . -178.4(4) ?
C31 C32 C33 C28 . . . . -0.5(6) ?
C31 C32 C33 C36 . . . . 179.1(4) ?
C29 C28 C33 C32 . . . . 0.4(5) ?
C5 C28 C33 C32 . . . . 177.7(3) ?
C29 C28 C33 C36 . . . . -179.1(4) ?
C5 C28 C33 C36 . . . . -1.8(5) ?
C2 C1 N1 C4 . . . . -0.9(4) ?
C10 C1 N1 C4 . . . . 175.5(3) ?
C2 C1 N1 B1 . . . . 171.1(3) ?
C10 C1 N1 B1 . . . . -12.4(5) ?
C5 C4 N1 C1 . . . . -170.7(3) ?
C3 C4 N1 C1 . . . . 1.5(4) ?
C5 C4 N1 B1 . . . . 16.9(5) ?
C3 C4 N1 B1 . . . . -171.0(3) ?
F1 B1 N1 C1 . . . . 46.3(5) ?
F2 B1 N1 C1 . . . . -75.6(4) ?
N2 B1 N1 C1 . . . . 166.1(3) ?
F1 B1 N1 C4 . . . . -142.7(3) ?
F2 B1 N1 C4 . . . . 95.3(4) ?
N2 B1 N1 C4 . . . . -23.0(4) ?
C8 C9 N2 C6 . . . . -0.6(3) ?
C19 C9 N2 C6 . . . . 175.8(3) ?
C8 C9 N2 B1 . . . . 176.2(3) ?
C19 C9 N2 B1 . . . . -7.4(5) ?
C5 C6 N2 C9 . . . . 174.3(3) ?
C7 C6 N2 C9 . . . . -0.2(3) ?
C5 C6 N2 B1 . . . . -2.8(5) ?
C7 C6 N2 B1 . . . . -177.3(3) ?
F1 B1 N2 C9 . . . . -40.1(5) ?
F2 B1 N2 C9 . . . . 82.1(4) ?
N1 B1 N2 C9 . . . . -160.5(3) ?
F1 B1 N2 C6 . . . . 136.3(3) ?
F2 B1 N2 C6 . . . . -101.5(3) ?
N1 B1 N2 C6 . . . . 15.8(4) ?


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

data_02817JorgeLabella
_database_code_depnum_ccdc_archive 'CCDC 1985334'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles'
;Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            JL376-5_250K
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H29 B F2 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         538.42

_chemical_melting_point          ?

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

_cell_length_a                   14.395(4)
_cell_length_b                   14.038(3)
_cell_length_c                   18.526(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.639(11)
_cell_angle_gamma                90
_cell_volume                     3547.3(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7952
_cell_measurement_theta_min      2.7396
_cell_measurement_theta_max      20.2099
_cell_measurement_temperature    250.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'dark blue'
_exptl_crystal_size_max          0.980
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.137
_exptl_crystal_density_diffrn    1.008
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128

_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      250.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            93294
_diffrn_reflns_av_R_equivalents  0.0928
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;
;

_reflns_number_total             6466
_reflns_number_gt                3298
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1716
_refine_ls_R_factor_gt           0.0962
_refine_ls_wR_factor_gt          0.2819
_refine_ls_wR_factor_ref         0.3532
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_number_reflns         6466
_refine_ls_number_parameters     375
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²+1.9700P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.307
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.2024(3) 0.6338(3) 0.7682(3) 0.0529(11) Uani d . . . 1 . .
C C1 0.1022(3) 0.6276(3) 0.6203(2) 0.0544(10) Uani d . . . 1 . .
C C2 0.1261(3) 0.6207(3) 0.5519(2) 0.0580(11) Uani d . . . 1 . .
C C3 0.2267(3) 0.6129(3) 0.5721(2) 0.0591(11) Uani d . . . 1 . .
H H3 0.2637 0.6067 0.5387 0.071 Uiso calc U . R 1 . .
C C4 0.2632(3) 0.6160(3) 0.6518(2) 0.0529(10) Uani d . . . 1 . .
C C5 0.3601(3) 0.6102(3) 0.6975(2) 0.0536(10) Uani d . . . 1 . .
C C6 0.3852(3) 0.6163(3) 0.7773(2) 0.0551(10) Uani d . . . 1 . .
C C7 0.4781(3) 0.6121(3) 0.8316(3) 0.0632(12) Uani d . . . 1 . .
H H7 0.5381 0.6044 0.8221 0.076 Uiso calc U . R 1 . .
C C8 0.4649(3) 0.6213(3) 0.9023(2) 0.0623(12) Uani d . . . 1 . .
C C9 0.3623(3) 0.6314(3) 0.8894(2) 0.0585(11) Uani d . . . 1 . .
C C10 0.0012(3) 0.6342(3) 0.6173(3) 0.0665(12) Uani d . . . 1 . .
C C11 -0.0651(3) 0.6322(3) 0.5458(4) 0.0811(16) Uani d . . . 1 . .
H H11 -0.1315 0.6349 0.5425 0.097 Uiso calc U . R 1 . .
C C12 -0.0453(4) 0.6266(3) 0.4760(3) 0.0751(14) Uani d . . . 1 . .
C C13 -0.1203(5) 0.6266(3) 0.4054(4) 0.103(2) Uani d . . . 1 . .
H H13 -0.1862 0.6304 0.4034 0.124 Uiso calc U . R 1 . .
C C14 -0.0965(7) 0.6208(4) 0.3391(4) 0.122(3) Uani d . . . 1 . .
H H14 -0.1464 0.6215 0.2917 0.147 Uiso calc U . R 1 . .
C C15 -0.0022(7) 0.6143(4) 0.3420(3) 0.115(2) Uani d . . . 1 . .
H H15 0.0125 0.6091 0.2963 0.138 Uiso calc U . R 1 . .
C C16 0.0730(5) 0.6151(3) 0.4095(3) 0.0906(17) Uani d . . . 1 . .
H H16 0.1384 0.6117 0.4099 0.109 Uiso calc U . R 1 . .
C C17 0.0514(4) 0.6210(3) 0.4782(3) 0.0684(13) Uani d . . . 1 . .
C C18 -0.0309(4) 0.6416(4) 0.6873(4) 0.0936(17) Uani d . . . 1 . .
H H18A -0.1017 0.6472 0.6719 0.14 Uiso calc U . R 1 . .
H H18B -0.0012 0.6974 0.7165 0.14 Uiso calc U . R 1 . .
H H18C -0.0103 0.5851 0.7184 0.14 Uiso calc U . R 1 . .
C C19 0.3246(4) 0.6423(3) 0.9520(3) 0.0749(14) Uani d . . . 1 . .
C C20 0.3935(6) 0.6420(3) 1.0227(3) 0.0929(19) Uani d . . . 1 . .
H H20 0.3708 0.6492 1.0647 0.111 Uiso calc U . R 1 . .
C C21 0.4970(6) 0.6318(3) 1.0385(3) 0.0888(18) Uani d . . . 1 . .
C C22 0.5625(7) 0.6328(4) 1.1136(3) 0.118(3) Uani d . . . 1 . .
H H22 0.5374 0.6419 1.1541 0.141 Uiso calc U . R 1 . .
C C23 0.6578(8) 0.6214(4) 1.1290(4) 0.136(4) Uani d . . . 1 . .
H H23 0.6997 0.6233 1.1797 0.163 Uiso calc U . R 1 . .
C C24 0.6950(6) 0.6068(4) 1.0708(5) 0.128(3) Uani d . . . 1 . .
H H24 0.7625 0.5957 1.082 0.154 Uiso calc U . R 1 . .
C C25 0.6337(5) 0.6082(3) 0.9939(3) 0.104(2) Uani d . . . 1 . .
H H25 0.6602 0.6008 0.954 0.124 Uiso calc U . R 1 . .
C C26 0.5340(4) 0.6204(3) 0.9789(3) 0.0765(15) Uani d . . . 1 . .
C C27 0.2198(5) 0.6541(4) 0.9448(3) 0.0983(18) Uani d . . . 1 . .
H H27A 0.2136 0.6652 0.9947 0.147 Uiso calc U . R 1 . .
H H27B 0.1841 0.5969 0.9228 0.147 Uiso calc U . R 1 . .
H H27C 0.1931 0.7081 0.912 0.147 Uiso calc U . R 1 . .
C C28 0.4390(3) 0.5961(3) 0.6620(2) 0.0581(11) Uani d . . . 1 . .
C C29 0.4693(3) 0.5051(3) 0.6511(2) 0.0630(11) Uani d . . . 1 . .
C C30 0.5419(3) 0.4954(4) 0.6172(3) 0.0806(14) Uani d . . . 1 . .
H H30 0.563 0.4338 0.61 0.097 Uiso calc U . R 1 . .
C C31 0.5844(4) 0.5718(5) 0.5937(3) 0.0865(15) Uani d . . . 1 . .
C C32 0.5527(4) 0.6611(5) 0.6048(4) 0.1002(18) Uani d . . . 1 . .
H H32 0.5805 0.7145 0.589 0.12 Uiso calc U . R 1 . .
C C33 0.4805(4) 0.6747(4) 0.6389(3) 0.0856(15) Uani d . . . 1 . .
C C34 0.4255(4) 0.4186(4) 0.6747(4) 0.0947(17) Uani d . . . 1 . .
H H34A 0.4621 0.3626 0.6691 0.142 Uiso calc U . R 1 . .
H H34B 0.3578 0.4121 0.6428 0.142 Uiso calc U . R 1 . .
H H34C 0.4284 0.425 0.7275 0.142 Uiso calc U . R 1 . .
C C35 0.6654(4) 0.5581(6) 0.5585(4) 0.123(2) Uani d . . . 1 . .
H H35A 0.6738 0.6163 0.533 0.185 Uiso calc U . R 1 . .
H H35B 0.6479 0.5064 0.5218 0.185 Uiso calc U . R 1 . .
H H35C 0.7262 0.5427 0.5981 0.185 Uiso calc U . R 1 . .
C C36 0.4463(7) 0.7751(4) 0.6484(5) 0.162(4) Uani d . . . 1 . .
H H36A 0.4738 0.7944 0.7013 0.243 Uiso calc U . R 1 . .
H H36B 0.3753 0.7762 0.6337 0.243 Uiso calc U . R 1 . .
H H36C 0.468 0.8186 0.6164 0.243 Uiso calc U . R 1 . .
F F1 0.16741(18) 0.72132(16) 0.78258(13) 0.0693(7) Uani d . . . 1 . .
F F2 0.15463(18) 0.55971(17) 0.79119(13) 0.0721(8) Uani d . . . 1 . .
N N1 0.1868(2) 0.6255(2) 0.68150(18) 0.0509(8) Uani d . . . 1 . .
N N2 0.3138(2) 0.6277(2) 0.81246(18) 0.0543(9) Uani d . . . 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 F1 . 1.385(5) ?
B1 F2 . 1.387(5) ?
B1 N2 . 1.552(6) ?
B1 N1 . 1.554(6) ?
C1 N1 . 1.374(5) ?
C1 C2 . 1.419(6) ?
C1 C10 . 1.440(6) ?
C2 C3 . 1.378(6) ?
C2 C17 . 1.443(6) ?
C3 C4 . 1.401(6) ?
C3 H3 . 0.94 ?
C4 N1 . 1.384(5) ?
C4 C5 . 1.384(6) ?
C5 C6 . 1.407(6) ?
C5 C28 . 1.496(6) ?
C6 N2 . 1.391(5) ?
C6 C7 . 1.395(6) ?
C7 C8 . 1.389(6) ?
C7 H7 . 0.94 ?
C8 C9 . 1.426(7) ?
C8 C26 . 1.450(6) ?
C9 N2 . 1.374(5) ?
C9 C19 . 1.437(7) ?
C10 C11 . 1.363(7) ?
C10 C18 . 1.513(7) ?
C11 C12 . 1.412(8) ?
C11 H11 . 0.94 ?
C12 C17 . 1.382(7) ?
C12 C13 . 1.404(7) ?
C13 C14 . 1.379(11) ?
C13 H13 . 0.94 ?
C14 C15 . 1.345(11) ?
C14 H14 . 0.94 ?
C15 C16 . 1.367(8) ?
C15 H15 . 0.94 ?
C16 C17 . 1.407(7) ?
C16 H16 . 0.94 ?
C18 H18A . 0.97 ?
C18 H18B . 0.97 ?
C18 H18C . 0.97 ?
C19 C20 . 1.367(7) ?
C19 C27 . 1.480(8) ?
C20 C21 . 1.430(9) ?
C20 H20 . 0.94 ?
C21 C26 . 1.382(8) ?
C21 C22 . 1.409(8) ?
C22 C23 . 1.318(12) ?
C22 H22 . 0.94 ?
C23 C24 . 1.364(12) ?
C23 H23 . 0.94 ?
C24 C25 . 1.416(9) ?
C24 H24 . 0.94 ?
C25 C26 . 1.382(8) ?
C25 H25 . 0.94 ?
C27 H27A . 0.97 ?
C27 H27B . 0.97 ?
C27 H27C . 0.97 ?
C28 C33 . 1.386(7) ?
C28 C29 . 1.386(6) ?
C29 C30 . 1.389(6) ?
C29 C34 . 1.496(7) ?
C30 C31 . 1.372(7) ?
C30 H30 . 0.94 ?
C31 C32 . 1.371(8) ?
C31 C35 . 1.519(7) ?
C32 C33 . 1.391(7) ?
C32 H32 . 0.94 ?
C33 C36 . 1.521(8) ?
C34 H34A . 0.97 ?
C34 H34B . 0.97 ?
C34 H34C . 0.97 ?
C35 H35A . 0.97 ?
C35 H35B . 0.97 ?
C35 H35C . 0.97 ?
C36 H36A . 0.97 ?
C36 H36B . 0.97 ?
C36 H36C . 0.97 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 B1 F2 . . 111.1(3) ?
F1 B1 N2 . . 109.0(3) ?
F2 B1 N2 . . 109.1(3) ?
F1 B1 N1 . . 108.9(3) ?
F2 B1 N1 . . 109.8(3) ?
N2 B1 N1 . . 109.0(3) ?
N1 C1 C2 . . 109.3(4) ?
N1 C1 C10 . . 130.6(4) ?
C2 C1 C10 . . 120.0(4) ?
C3 C2 C1 . . 107.3(4) ?
C3 C2 C17 . . 131.1(4) ?
C1 C2 C17 . . 121.6(4) ?
C2 C3 C4 . . 106.9(4) ?
C2 C3 H3 . . 126.5 ?
C4 C3 H3 . . 126.5 ?
N1 C4 C5 . . 122.4(4) ?
N1 C4 C3 . . 110.1(4) ?
C5 C4 C3 . . 127.5(4) ?
C4 C5 C6 . . 120.6(4) ?
C4 C5 C28 . . 119.7(4) ?
C6 C5 C28 . . 119.6(4) ?
N2 C6 C7 . . 110.4(4) ?
N2 C6 C5 . . 121.3(4) ?
C7 C6 C5 . . 128.3(4) ?
C8 C7 C6 . . 106.7(4) ?
C8 C7 H7 . . 126.7 ?
C6 C7 H7 . . 126.7 ?
C7 C8 C9 . . 107.4(4) ?
C7 C8 C26 . . 131.6(5) ?
C9 C8 C26 . . 121.0(5) ?
N2 C9 C8 . . 109.0(4) ?
N2 C9 C19 . . 130.1(4) ?
C8 C9 C19 . . 121.0(4) ?
C11 C10 C1 . . 114.9(5) ?
C11 C10 C18 . . 121.6(4) ?
C1 C10 C18 . . 123.5(4) ?
C10 C11 C12 . . 127.5(5) ?
C10 C11 H11 . . 116.3 ?
C12 C11 H11 . . 116.3 ?
C17 C12 C13 . . 119.7(6) ?
C17 C12 C11 . . 118.1(4) ?
C13 C12 C11 . . 122.2(6) ?
C14 C13 C12 . . 119.6(7) ?
C14 C13 H13 . . 120.2 ?
C12 C13 H13 . . 120.2 ?
C15 C14 C13 . . 120.2(6) ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C14 C15 C16 . . 122.0(7) ?
C14 C15 H15 . . 119.0 ?
C16 C15 H15 . . 119.0 ?
C15 C16 C17 . . 119.2(7) ?
C15 C16 H16 . . 120.4 ?
C17 C16 H16 . . 120.4 ?
C12 C17 C16 . . 119.2(5) ?
C12 C17 C2 . . 117.9(5) ?
C16 C17 C2 . . 122.8(5) ?
C10 C18 H18A . . 109.5 ?
C10 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C10 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C20 C19 C9 . . 115.3(5) ?
C20 C19 C27 . . 119.6(5) ?
C9 C19 C27 . . 125.1(4) ?
C19 C20 C21 . . 125.9(5) ?
C19 C20 H20 . . 117.1 ?
C21 C20 H20 . . 117.1 ?
C26 C21 C22 . . 118.9(7) ?
C26 C21 C20 . . 119.4(5) ?
C22 C21 C20 . . 121.8(7) ?
C23 C22 C21 . . 122.4(8) ?
C23 C22 H22 . . 118.8 ?
C21 C22 H22 . . 118.8 ?
C22 C23 C24 . . 119.4(7) ?
C22 C23 H23 . . 120.3 ?
C24 C23 H23 . . 120.3 ?
C23 C24 C25 . . 121.2(8) ?
C23 C24 H24 . . 119.4 ?
C25 C24 H24 . . 119.4 ?
C26 C25 C24 . . 118.5(7) ?
C26 C25 H25 . . 120.7 ?
C24 C25 H25 . . 120.7 ?
C25 C26 C21 . . 119.6(5) ?
C25 C26 C8 . . 122.8(6) ?
C21 C26 C8 . . 117.5(5) ?
C19 C27 H27A . . 109.5 ?
C19 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C19 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C33 C28 C29 . . 120.2(4) ?
C33 C28 C5 . . 119.5(4) ?
C29 C28 C5 . . 120.3(4) ?
C28 C29 C30 . . 118.3(4) ?
C28 C29 C34 . . 121.7(4) ?
C30 C29 C34 . . 120.1(4) ?
C31 C30 C29 . . 122.9(5) ?
C31 C30 H30 . . 118.6 ?
C29 C30 H30 . . 118.6 ?
C32 C31 C30 . . 117.6(5) ?
C32 C31 C35 . . 121.2(6) ?
C30 C31 C35 . . 121.1(6) ?
C31 C32 C33 . . 121.8(5) ?
C31 C32 H32 . . 119.1 ?
C33 C32 H32 . . 119.1 ?
C28 C33 C32 . . 119.3(5) ?
C28 C33 C36 . . 120.9(5) ?
C32 C33 C36 . . 119.8(5) ?
C29 C34 H34A . . 109.5 ?
C29 C34 H34B . . 109.5 ?
H34A C34 H34B . . 109.5 ?
C29 C34 H34C . . 109.5 ?
H34A C34 H34C . . 109.5 ?
H34B C34 H34C . . 109.5 ?
C31 C35 H35A . . 109.5 ?
C31 C35 H35B . . 109.5 ?
H35A C35 H35B . . 109.5 ?
C31 C35 H35C . . 109.5 ?
H35A C35 H35C . . 109.5 ?
H35B C35 H35C . . 109.5 ?
C33 C36 H36A . . 109.5 ?
C33 C36 H36B . . 109.5 ?
H36A C36 H36B . . 109.5 ?
C33 C36 H36C . . 109.5 ?
H36A C36 H36C . . 109.5 ?
H36B C36 H36C . . 109.5 ?
C1 N1 C4 . . 106.3(3) ?
C1 N1 B1 . . 130.5(3) ?
C4 N1 B1 . . 123.2(3) ?
C9 N2 C6 . . 106.5(3) ?
C9 N2 B1 . . 130.0(4) ?
C6 N2 B1 . . 123.5(3) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . 0.8(4) ?
C10 C1 C2 C3 . . . . -178.4(3) ?
N1 C1 C2 C17 . . . . 179.9(3) ?
C10 C1 C2 C17 . . . . 0.7(5) ?
C1 C2 C3 C4 . . . . -0.5(4) ?
C17 C2 C3 C4 . . . . -179.5(4) ?
C2 C3 C4 N1 . . . . 0.1(4) ?
C2 C3 C4 C5 . . . . 179.7(4) ?
N1 C4 C5 C6 . . . . -1.6(6) ?
C3 C4 C5 C6 . . . . 178.8(4) ?
N1 C4 C5 C28 . . . . 177.6(4) ?
C3 C4 C5 C28 . . . . -2.0(6) ?
C4 C5 C6 N2 . . . . 0.2(6) ?
C28 C5 C6 N2 . . . . -178.9(3) ?
C4 C5 C6 C7 . . . . -179.9(4) ?
C28 C5 C6 C7 . . . . 1.0(6) ?
N2 C6 C7 C8 . . . . -0.1(4) ?
C5 C6 C7 C8 . . . . 180.0(4) ?
C6 C7 C8 C9 . . . . -0.2(4) ?
C6 C7 C8 C26 . . . . 178.7(4) ?
C7 C8 C9 N2 . . . . 0.4(4) ?
C26 C8 C9 N2 . . . . -178.6(3) ?
C7 C8 C9 C19 . . . . 179.9(4) ?
C26 C8 C9 C19 . . . . 0.8(6) ?
N1 C1 C10 C11 . . . . -178.5(4) ?
C2 C1 C10 C11 . . . . 0.5(5) ?
N1 C1 C10 C18 . . . . 0.9(7) ?
C2 C1 C10 C18 . . . . 179.9(4) ?
C1 C10 C11 C12 . . . . -1.4(6) ?
C18 C10 C11 C12 . . . . 179.2(4) ?
C10 C11 C12 C17 . . . . 1.0(7) ?
C10 C11 C12 C13 . . . . -179.0(4) ?
C17 C12 C13 C14 . . . . 0.0(7) ?
C11 C12 C13 C14 . . . . -179.9(5) ?
C12 C13 C14 C15 . . . . 0.7(9) ?
C13 C14 C15 C16 . . . . -1.4(10) ?
C14 C15 C16 C17 . . . . 1.3(8) ?
C13 C12 C17 C16 . . . . -0.1(6) ?
C11 C12 C17 C16 . . . . 179.8(4) ?
C13 C12 C17 C2 . . . . -179.7(4) ?
C11 C12 C17 C2 . . . . 0.3(6) ?
C15 C16 C17 C12 . . . . -0.6(7) ?
C15 C16 C17 C2 . . . . 179.0(4) ?
C3 C2 C17 C12 . . . . 177.8(4) ?
C1 C2 C17 C12 . . . . -1.1(5) ?
C3 C2 C17 C16 . . . . -1.8(7) ?
C1 C2 C17 C16 . . . . 179.4(4) ?
N2 C9 C19 C20 . . . . 179.3(4) ?
C8 C9 C19 C20 . . . . 0.0(6) ?
N2 C9 C19 C27 . . . . -1.3(7) ?
C8 C9 C19 C27 . . . . 179.4(4) ?
C9 C19 C20 C21 . . . . -0.2(7) ?
C27 C19 C20 C21 . . . . -179.7(5) ?
C19 C20 C21 C26 . . . . -0.3(7) ?
C19 C20 C21 C22 . . . . 179.7(4) ?
C26 C21 C22 C23 . . . . -1.4(8) ?
C20 C21 C22 C23 . . . . 178.5(6) ?
C21 C22 C23 C24 . . . . -0.9(10) ?
C22 C23 C24 C25 . . . . 3.0(10) ?
C23 C24 C25 C26 . . . . -2.8(8) ?
C24 C25 C26 C21 . . . . 0.5(7) ?
C24 C25 C26 C8 . . . . -178.9(4) ?
C22 C21 C26 C25 . . . . 1.5(6) ?
C20 C21 C26 C25 . . . . -178.4(4) ?
C22 C21 C26 C8 . . . . -179.0(4) ?
C20 C21 C26 C8 . . . . 1.1(6) ?
C7 C8 C26 C25 . . . . -0.6(7) ?
C9 C8 C26 C25 . . . . 178.1(4) ?
C7 C8 C26 C21 . . . . 179.9(4) ?
C9 C8 C26 C21 . . . . -1.3(6) ?
C4 C5 C28 C33 . . . . 87.7(5) ?
C6 C5 C28 C33 . . . . -93.1(5) ?
C4 C5 C28 C29 . . . . -91.4(5) ?
C6 C5 C28 C29 . . . . 87.8(5) ?
C33 C28 C29 C30 . . . . 0.3(7) ?
C5 C28 C29 C30 . . . . 179.3(4) ?
C33 C28 C29 C34 . . . . -179.5(5) ?
C5 C28 C29 C34 . . . . -0.4(7) ?
C28 C29 C30 C31 . . . . -0.3(7) ?
C34 C29 C30 C31 . . . . 179.4(5) ?
C29 C30 C31 C32 . . . . 0.1(8) ?
C29 C30 C31 C35 . . . . 178.5(5) ?
C30 C31 C32 C33 . . . . 0.3(9) ?
C35 C31 C32 C33 . . . . -178.2(6) ?
C29 C28 C33 C32 . . . . 0.0(8) ?
C5 C28 C33 C32 . . . . -179.0(5) ?
C29 C28 C33 C36 . . . . 178.4(6) ?
C5 C28 C33 C36 . . . . -0.7(8) ?
C31 C32 C33 C28 . . . . -0.3(9) ?
C31 C32 C33 C36 . . . . -178.7(6) ?
C2 C1 N1 C4 . . . . -0.8(4) ?
C10 C1 N1 C4 . . . . 178.3(4) ?
C2 C1 N1 B1 . . . . 177.9(3) ?
C10 C1 N1 B1 . . . . -3.0(6) ?
C5 C4 N1 C1 . . . . -179.2(3) ?
C3 C4 N1 C1 . . . . 0.4(4) ?
C5 C4 N1 B1 . . . . 2.0(6) ?
C3 C4 N1 B1 . . . . -178.3(3) ?
F1 B1 N1 C1 . . . . -60.7(5) ?
F2 B1 N1 C1 . . . . 61.1(5) ?
N2 B1 N1 C1 . . . . -179.5(3) ?
F1 B1 N1 C4 . . . . 117.7(4) ?
F2 B1 N1 C4 . . . . -120.5(4) ?
N2 B1 N1 C4 . . . . -1.1(5) ?
C8 C9 N2 C6 . . . . -0.5(4) ?
C19 C9 N2 C6 . . . . -179.9(4) ?
C8 C9 N2 B1 . . . . 179.2(4) ?
C19 C9 N2 B1 . . . . -0.2(6) ?
C7 C6 N2 C9 . . . . 0.4(4) ?
C5 C6 N2 C9 . . . . -179.7(3) ?
C7 C6 N2 B1 . . . . -179.3(3) ?
C5 C6 N2 B1 . . . . 0.6(5) ?
F1 B1 N2 C9 . . . . 61.5(5) ?
F2 B1 N2 C9 . . . . -59.9(5) ?
N1 B1 N2 C9 . . . . -179.8(3) ?
F1 B1 N2 C6 . . . . -119.0(4) ?
F2 B1 N2 C6 . . . . 119.6(4) ?
N1 B1 N2 C6 . . . . -0.2(5) ?


####################################################################### 
# 
# 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_02884JorgeLabella
_database_code_depnum_ccdc_archive 'CCDC 1985333'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles'
;Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            JL376-21DEHIDRO
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H25 B F2 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         474.34

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9160(14)
_cell_length_b                   10.089(2)
_cell_length_c                   15.968(3)
_cell_angle_alpha                79.032(11)
_cell_angle_beta                 88.721(10)
_cell_angle_gamma                85.253(10)
_cell_volume                     1247.7(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8812
_cell_measurement_theta_min      2.2203
_cell_measurement_theta_max      26.0791
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'dark purple'
_exptl_crystal_size_max          0.366
_exptl_crystal_size_mid          0.295
_exptl_crystal_size_min          0.054
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496

_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            62317
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_theta_min         1.30
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             4551
_reflns_number_gt                3806
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1632
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_number_reflns         4551
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1024P)²+0.3569P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.396
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.6397(3) 0.53515(19) 0.78663(12) 0.0417(4) Uani d . . . 1 . .
C C1 0.7154(2) 0.53356(17) 0.94321(11) 0.0424(4) Uani d . . . 1 . .
H H1 0.7955 0.4596 0.9486 0.051 Uiso calc U . R 1 . .
C C2 0.6681(2) 0.60346(18) 1.00794(11) 0.0463(4) Uani d . . . 1 . .
H H2 0.7098 0.5855 1.0633 0.056 Uiso calc U . R 1 . .
C C3 0.5473(2) 0.70457(17) 0.97452(11) 0.0426(4) Uani d . . . 1 . .
H H3 0.4919 0.7678 1.0032 0.051 Uiso calc U . R 1 . .
C C4 0.5230(2) 0.69481(16) 0.88931(10) 0.0364(4) Uani d . . . 1 . .
C C5 0.41379(19) 0.77041(15) 0.82698(10) 0.0347(4) Uani d . . . 1 . .
C C6 0.4105(2) 0.73931(16) 0.74638(10) 0.0361(4) Uani d . . . 1 . .
C C7 0.3107(2) 0.79625(17) 0.67472(10) 0.0388(4) Uani d . . . 1 . .
H H7 0.2292 0.8689 0.6715 0.047 Uiso calc U . R 1 . .
C C8 0.3538(2) 0.72643(17) 0.61023(10) 0.0389(4) Uani d . . . 1 . .
C C9 0.4841(2) 0.62754(17) 0.64419(10) 0.0396(4) Uani d . . . 1 . .
H H9 0.5395 0.5661 0.6142 0.048 Uiso calc U . R 1 . .
C C10 0.2990(2) 0.88495(16) 0.84753(10) 0.0365(4) Uani d . . . 1 . .
C C11 0.1279(2) 0.86597(18) 0.86539(10) 0.0413(4) Uani d . . . 1 . .
C C12 0.0242(2) 0.9758(2) 0.88277(12) 0.0521(5) Uani d . . . 1 . .
H H12 -0.0892 0.9641 0.8961 0.063 Uiso calc U . R 1 . .
C C13 0.0826(3) 1.1013(2) 0.88099(12) 0.0529(5) Uani d . . . 1 . .
C C14 0.2522(3) 1.11628(19) 0.86387(13) 0.0533(5) Uani d . . . 1 . .
H H14 0.2938 1.2 0.8632 0.064 Uiso calc U . R 1 . .
C C15 0.3625(2) 1.00986(18) 0.84757(12) 0.0466(4) Uani d . . . 1 . .
C C16 0.0561(3) 0.7328(2) 0.86633(14) 0.0587(5) Uani d . . . 1 . .
H H16A -0.0592 0.737 0.8863 0.088 Uiso calc U . R 1 . .
H H16B 0.1219 0.6624 0.9036 0.088 Uiso calc U . R 1 . .
H H16C 0.0595 0.7136 0.8097 0.088 Uiso calc U . R 1 . .
C C17 -0.0351(3) 1.2197(3) 0.89659(17) 0.0787(8) Uani d . . . 1 . .
H H17A 0.0199 1.2693 0.9324 0.118 Uiso calc U . R 1 . .
H H17B -0.1367 1.1872 0.9242 0.118 Uiso calc U . R 1 . .
H H17C -0.0634 1.2782 0.8431 0.118 Uiso calc U . R 1 . .
C C18 0.5459(3) 1.0319(2) 0.8300(2) 0.0772(8) Uani d . . . 1 . .
H H18A 0.562 1.1264 0.8248 0.116 Uiso calc U . R 1 . .
H H18B 0.5798 1.0029 0.7778 0.116 Uiso calc U . R 1 . .
H H18C 0.6133 0.9806 0.8761 0.116 Uiso calc U . R 1 . .
C C19 0.2787(2) 0.74223(18) 0.52461(10) 0.0426(4) Uani d . . . 1 . .
C C20 0.2401(2) 0.8739(2) 0.47307(11) 0.0466(4) Uani d . . . 1 . .
C C21 0.2779(3) 0.9955(2) 0.49729(13) 0.0556(5) Uani d . . . 1 . .
H H21 0.3326 0.9915 0.5487 0.067 Uiso calc U . R 1 . .
C C22 0.2361(3) 1.1191(2) 0.44689(16) 0.0701(6) Uani d . . . 1 . .
H H22 0.2604 1.1976 0.4651 0.084 Uiso calc U . R 1 . .
C C23 0.1575(3) 1.1286(3) 0.36870(16) 0.0745(7) Uani d . . . 1 . .
H H23 0.1282 1.213 0.3352 0.089 Uiso calc U . R 1 . .
C C24 0.1240(3) 1.0148(3) 0.34183(13) 0.0701(7) Uani d . . . 1 . .
H H24 0.074 1.022 0.2888 0.084 Uiso calc U . R 1 . .
C C25 0.1630(2) 0.8843(2) 0.39201(12) 0.0557(5) Uani d . . . 1 . .
C C26 0.1280(3) 0.7655(3) 0.36440(14) 0.0702(7) Uani d . . . 1 . .
H H26 0.0778 0.7721 0.3115 0.084 Uiso calc U . R 1 . .
C C27 0.1658(3) 0.6408(3) 0.41310(14) 0.0667(6) Uani d . . . 1 . .
H H27 0.1421 0.5636 0.3931 0.08 Uiso calc U . R 1 . .
C C28 0.2409(2) 0.6280(2) 0.49400(12) 0.0503(5) Uani d . . . 1 . .
C C29 0.2747(3) 0.4946(2) 0.54387(14) 0.0555(5) Uani d . . . 1 . .
C C30 0.3067(3) 0.3840(2) 0.58448(15) 0.0625(6) Uani d . . . 1 . .
C C31 0.3530(4) 0.2533(3) 0.6384(2) 0.0905(8) Uani d . . . 1 . .
H H31A 0.4427 0.2062 0.6115 0.136 Uiso calc U . R 1 . .
H H31B 0.2563 0.2007 0.6465 0.136 Uiso calc U . R 1 . .
H H31C 0.3907 0.2668 0.6927 0.136 Uiso calc U . R 1 . .
F F1 0.58718(19) 0.40651(11) 0.79849(8) 0.0693(4) Uani d . . . 1 . .
F F2 0.80234(14) 0.53644(14) 0.75455(7) 0.0661(4) Uani d . . . 1 . .
N N1 0.62963(17) 0.58757(13) 0.87157(8) 0.0367(3) Uani d . . . 1 . .
N N2 0.51716(17) 0.63379(13) 0.72441(8) 0.0368(3) Uani d . . . 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 F1 . 1.373(2) ?
B1 F2 . 1.375(2) ?
B1 N1 . 1.545(2) ?
B1 N2 . 1.558(2) ?
C1 N1 . 1.343(2) ?
C1 C2 . 1.387(3) ?
C1 H1 . 0.93 ?
C2 C3 . 1.376(2) ?
C2 H2 . 0.93 ?
C3 C4 . 1.401(2) ?
C3 H3 . 0.93 ?
C4 N1 . 1.385(2) ?
C4 C5 . 1.400(2) ?
C5 C6 . 1.383(2) ?
C5 C10 . 1.492(2) ?
C6 N2 . 1.3964(19) ?
C6 C7 . 1.407(2) ?
C7 C8 . 1.376(2) ?
C7 H7 . 0.93 ?
C8 C9 . 1.415(2) ?
C8 C19 . 1.479(2) ?
C9 N2 . 1.327(2) ?
C9 H9 . 0.93 ?
C10 C15 . 1.395(3) ?
C10 C11 . 1.399(2) ?
C11 C12 . 1.391(3) ?
C11 C16 . 1.499(3) ?
C12 C13 . 1.378(3) ?
C12 H12 . 0.93 ?
C13 C14 . 1.379(3) ?
C13 C17 . 1.509(3) ?
C14 C15 . 1.387(2) ?
C14 H14 . 0.93 ?
C15 C18 . 1.499(3) ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
C19 C28 . 1.391(3) ?
C19 C20 . 1.436(3) ?
C20 C21 . 1.411(3) ?
C20 C25 . 1.426(3) ?
C21 C22 . 1.369(3) ?
C21 H21 . 0.93 ?
C22 C23 . 1.391(4) ?
C22 H22 . 0.93 ?
C23 C24 . 1.347(4) ?
C23 H23 . 0.93 ?
C24 C25 . 1.419(3) ?
C24 H24 . 0.93 ?
C25 C26 . 1.404(3) ?
C26 C27 . 1.361(4) ?
C26 H26 . 0.93 ?
C27 C28 . 1.413(3) ?
C27 H27 . 0.93 ?
C28 C29 . 1.435(3) ?
C29 C30 . 1.189(3) ?
C30 C31 . 1.455(4) ?
C31 H31A . 0.96 ?
C31 H31B . 0.96 ?
C31 H31C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 B1 F2 . . 110.17(15) ?
F1 B1 N1 . . 110.26(15) ?
F2 B1 N1 . . 110.47(15) ?
F1 B1 N2 . . 109.66(15) ?
F2 B1 N2 . . 110.19(15) ?
N1 B1 N2 . . 106.00(12) ?
N1 C1 C2 . . 110.51(15) ?
N1 C1 H1 . . 124.7 ?
C2 C1 H1 . . 124.7 ?
C3 C2 C1 . . 106.77(15) ?
C3 C2 H2 . . 126.6 ?
C1 C2 H2 . . 126.6 ?
C2 C3 C4 . . 107.45(15) ?
C2 C3 H3 . . 126.3 ?
C4 C3 H3 . . 126.3 ?
N1 C4 C5 . . 120.76(14) ?
N1 C4 C3 . . 108.05(14) ?
C5 C4 C3 . . 131.18(15) ?
C6 C5 C4 . . 120.52(14) ?
C6 C5 C10 . . 119.52(14) ?
C4 C5 C10 . . 119.95(14) ?
C5 C6 N2 . . 121.22(14) ?
C5 C6 C7 . . 131.29(14) ?
N2 C6 C7 . . 107.48(13) ?
C8 C7 C6 . . 108.56(14) ?
C8 C7 H7 . . 125.7 ?
C6 C7 H7 . . 125.7 ?
C7 C8 C9 . . 105.23(14) ?
C7 C8 C19 . . 129.23(15) ?
C9 C8 C19 . . 125.47(15) ?
N2 C9 C8 . . 111.27(14) ?
N2 C9 H9 . . 124.4 ?
C8 C9 H9 . . 124.4 ?
C15 C10 C11 . . 120.81(15) ?
C15 C10 C5 . . 119.85(15) ?
C11 C10 C5 . . 119.34(15) ?
C12 C11 C10 . . 117.70(17) ?
C12 C11 C16 . . 120.22(17) ?
C10 C11 C16 . . 122.08(16) ?
C13 C12 C11 . . 122.69(18) ?
C13 C12 H12 . . 118.7 ?
C11 C12 H12 . . 118.7 ?
C12 C13 C14 . . 118.12(16) ?
C12 C13 C17 . . 121.3(2) ?
C14 C13 C17 . . 120.6(2) ?
C13 C14 C15 . . 121.81(19) ?
C13 C14 H14 . . 119.1 ?
C15 C14 H14 . . 119.1 ?
C14 C15 C10 . . 118.84(17) ?
C14 C15 C18 . . 119.41(18) ?
C10 C15 C18 . . 121.75(16) ?
C11 C16 H16A . . 109.5 ?
C11 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C11 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C13 C17 H17A . . 109.5 ?
C13 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C13 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C15 C18 H18A . . 109.5 ?
C15 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C15 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C28 C19 C20 . . 119.23(16) ?
C28 C19 C8 . . 119.60(16) ?
C20 C19 C8 . . 121.16(16) ?
C21 C20 C25 . . 117.29(18) ?
C21 C20 C19 . . 123.52(16) ?
C25 C20 C19 . . 119.17(19) ?
C22 C21 C20 . . 121.6(2) ?
C22 C21 H21 . . 119.2 ?
C20 C21 H21 . . 119.2 ?
C21 C22 C23 . . 120.7(3) ?
C21 C22 H22 . . 119.6 ?
C23 C22 H22 . . 119.6 ?
C24 C23 C22 . . 119.6(2) ?
C24 C23 H23 . . 120.2 ?
C22 C23 H23 . . 120.2 ?
C23 C24 C25 . . 121.9(2) ?
C23 C24 H24 . . 119.0 ?
C25 C24 H24 . . 119.0 ?
C26 C25 C24 . . 122.1(2) ?
C26 C25 C20 . . 119.1(2) ?
C24 C25 C20 . . 118.8(2) ?
C27 C26 C25 . . 121.64(19) ?
C27 C26 H26 . . 119.2 ?
C25 C26 H26 . . 119.2 ?
C26 C27 C28 . . 120.3(2) ?
C26 C27 H27 . . 119.9 ?
C28 C27 H27 . . 119.9 ?
C19 C28 C27 . . 120.6(2) ?
C19 C28 C29 . . 121.15(17) ?
C27 C28 C29 . . 118.23(19) ?
C30 C29 C28 . . 178.4(2) ?
C29 C30 C31 . . 175.7(3) ?
C30 C31 H31A . . 109.5 ?
C30 C31 H31B . . 109.5 ?
H31A C31 H31B . . 109.5 ?
C30 C31 H31C . . 109.5 ?
H31A C31 H31C . . 109.5 ?
H31B C31 H31C . . 109.5 ?
C1 N1 C4 . . 107.24(14) ?
C1 N1 B1 . . 126.55(14) ?
C4 N1 B1 . . 126.13(13) ?
C9 N2 C6 . . 107.45(13) ?
C9 N2 B1 . . 127.20(13) ?
C6 N2 B1 . . 125.14(13) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . 0.2(2) ?
C1 C2 C3 C4 . . . . -0.1(2) ?
C2 C3 C4 N1 . . . . 0.0(2) ?
C2 C3 C4 C5 . . . . 178.75(18) ?
N1 C4 C5 C6 . . . . 0.0(2) ?
C3 C4 C5 C6 . . . . -178.70(17) ?
N1 C4 C5 C10 . . . . 179.57(14) ?
C3 C4 C5 C10 . . . . 0.9(3) ?
C4 C5 C6 N2 . . . . -1.1(2) ?
C10 C5 C6 N2 . . . . 179.32(14) ?
C4 C5 C6 C7 . . . . 177.95(17) ?
C10 C5 C6 C7 . . . . -1.7(3) ?
C5 C6 C7 C8 . . . . -178.57(18) ?
N2 C6 C7 C8 . . . . 0.56(19) ?
C6 C7 C8 C9 . . . . -1.00(19) ?
C6 C7 C8 C19 . . . . 176.08(17) ?
C7 C8 C9 N2 . . . . 1.1(2) ?
C19 C8 C9 N2 . . . . -176.09(16) ?
C6 C5 C10 C15 . . . . -100.91(19) ?
C4 C5 C10 C15 . . . . 79.5(2) ?
C6 C5 C10 C11 . . . . 78.2(2) ?
C4 C5 C10 C11 . . . . -101.39(18) ?
C15 C10 C11 C12 . . . . 0.2(2) ?
C5 C10 C11 C12 . . . . -178.87(15) ?
C15 C10 C11 C16 . . . . -179.64(17) ?
C5 C10 C11 C16 . . . . 1.3(2) ?
C10 C11 C12 C13 . . . . 1.6(3) ?
C16 C11 C12 C13 . . . . -178.57(17) ?
C11 C12 C13 C14 . . . . -2.1(3) ?
C11 C12 C13 C17 . . . . 177.44(18) ?
C12 C13 C14 C15 . . . . 0.9(3) ?
C17 C13 C14 C15 . . . . -178.67(19) ?
C13 C14 C15 C10 . . . . 0.8(3) ?
C13 C14 C15 C18 . . . . -179.6(2) ?
C11 C10 C15 C14 . . . . -1.4(3) ?
C5 C10 C15 C14 . . . . 177.72(16) ?
C11 C10 C15 C18 . . . . 179.0(2) ?
C5 C10 C15 C18 . . . . -1.9(3) ?
C7 C8 C19 C28 . . . . -133.9(2) ?
C9 C8 C19 C28 . . . . 42.6(3) ?
C7 C8 C19 C20 . . . . 44.6(3) ?
C9 C8 C19 C20 . . . . -138.87(18) ?
C28 C19 C20 C21 . . . . -178.08(17) ?
C8 C19 C20 C21 . . . . 3.4(3) ?
C28 C19 C20 C25 . . . . 0.4(3) ?
C8 C19 C20 C25 . . . . -178.10(15) ?
C25 C20 C21 C22 . . . . 2.7(3) ?
C19 C20 C21 C22 . . . . -178.76(19) ?
C20 C21 C22 C23 . . . . -1.4(3) ?
C21 C22 C23 C24 . . . . -0.8(4) ?
C22 C23 C24 C25 . . . . 1.5(4) ?
C23 C24 C25 C26 . . . . 179.8(2) ?
C23 C24 C25 C20 . . . . -0.2(3) ?
C21 C20 C25 C26 . . . . 178.09(18) ?
C19 C20 C25 C26 . . . . -0.5(3) ?
C21 C20 C25 C24 . . . . -1.9(3) ?
C19 C20 C25 C24 . . . . 179.47(17) ?
C24 C25 C26 C27 . . . . -179.9(2) ?
C20 C25 C26 C27 . . . . 0.0(3) ?
C25 C26 C27 C28 . . . . 0.5(4) ?
C20 C19 C28 C27 . . . . 0.1(3) ?
C8 C19 C28 C27 . . . . 178.67(17) ?
C20 C19 C28 C29 . . . . -178.99(17) ?
C8 C19 C28 C29 . . . . -0.4(3) ?
C26 C27 C28 C19 . . . . -0.6(3) ?
C26 C27 C28 C29 . . . . 178.5(2) ?
C2 C1 N1 C4 . . . . -0.2(2) ?
C2 C1 N1 B1 . . . . -176.99(17) ?
C5 C4 N1 C1 . . . . -178.77(15) ?
C3 C4 N1 C1 . . . . 0.17(19) ?
C5 C4 N1 B1 . . . . -2.0(3) ?
C3 C4 N1 B1 . . . . 176.93(16) ?
F1 B1 N1 C1 . . . . 61.8(2) ?
F2 B1 N1 C1 . . . . -60.2(2) ?
N2 B1 N1 C1 . . . . -179.61(15) ?
F1 B1 N1 C4 . . . . -114.38(17) ?
F2 B1 N1 C4 . . . . 123.60(17) ?
N2 B1 N1 C4 . . . . 4.2(2) ?
C8 C9 N2 C6 . . . . -0.80(19) ?
C8 C9 N2 B1 . . . . 174.19(16) ?
C5 C6 N2 C9 . . . . 179.38(16) ?
C7 C6 N2 C9 . . . . 0.15(19) ?
C5 C6 N2 B1 . . . . 4.3(3) ?
C7 C6 N2 B1 . . . . -174.98(15) ?
F1 B1 N2 C9 . . . . -60.5(2) ?
F2 B1 N2 C9 . . . . 61.0(2) ?
N1 B1 N2 C9 . . . . -179.48(15) ?
F1 B1 N2 C6 . . . . 113.69(18) ?
F2 B1 N2 C6 . . . . -124.87(17) ?
N1 B1 N2 C6 . . . . -5.3(2) ?


####################################################################### 
# 
# 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_02879JorgeLabella
_database_code_depnum_ccdc_archive 'CCDC 1985338'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles'
;Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            JL376-22DEH_200K
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H25 B F2 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         474.34

_chemical_melting_point          ?

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

_cell_length_a                   16.0345(7)
_cell_length_b                   8.5128(4)
_cell_length_c                   17.8694(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.426(2)
_cell_angle_gamma                90
_cell_volume                     2434.79(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9895
_cell_measurement_theta_min      2.5470
_cell_measurement_theta_max      25.7865
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'dark purple'
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.140
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992

_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      200.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            99869
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_theta_min         1.27
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
;

_reflns_number_total             4456
_reflns_number_gt                3750
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1078
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_number_reflns         4456
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0557P)²+0.7843P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F2 0.86006(5) 0.07339(10) 0.84089(5) 0.0419(2) Uani d . . . 1 . .
F F1 0.79446(6) 0.26947(11) 0.90086(4) 0.0435(2) Uani d . . . 1 . .
N N2 0.76016(7) 0.23389(13) 0.76818(6) 0.0259(3) Uani d . . . 1 . .
N N1 0.89921(7) 0.33701(13) 0.81705(6) 0.0274(3) Uani d . . . 1 . .
C C6 0.76715(8) 0.33505(15) 0.70775(7) 0.0256(3) Uani d . . . 1 . .
C C8 0.64628(8) 0.20267(15) 0.68472(7) 0.0255(3) Uani d . . . 1 . .
C C5 0.83498(8) 0.43733(15) 0.70178(7) 0.0257(3) Uani d . . . 1 . .
C C4 0.90024(9) 0.43750(16) 0.75586(7) 0.0276(3) Uani d . . . 1 . .
C C10 0.83779(8) 0.54489(16) 0.63603(7) 0.0264(3) Uani d . . . 1 . .
C C7 0.69873(8) 0.31729(16) 0.65697(7) 0.0269(3) Uani d . . . 1 . .
H H7 0.6892 0.3733 0.6113 0.032 Uiso calc U . R 1 . .
C C9 0.68610(8) 0.15426(15) 0.75537(7) 0.0259(3) Uani d . . . 1 . .
C C19 0.56595(8) 0.14017(16) 0.65844(8) 0.0286(3) Uani d . . . 1 . .
C C30 0.64811(9) 0.04346(16) 0.80258(8) 0.0317(3) Uani d . . . 1 . .
C C11 0.80670(9) 0.69763(17) 0.64066(8) 0.0317(3) Uani d . . . 1 . .
C C1 0.97148(9) 0.35635(17) 0.85719(8) 0.0329(3) Uani d . . . 1 . .
H H1 0.9872 0.3014 0.9021 0.039 Uiso calc U . R 1 . .
C C15 0.87251(9) 0.49156(17) 0.57060(8) 0.0318(3) Uani d . . . 1 . .
C C20 0.52149(9) 0.17686(17) 0.58770(8) 0.0318(3) Uani d . . . 1 . .
C C28 0.52903(9) 0.03671(18) 0.70788(8) 0.0357(3) Uani d . . . 1 . .
C C12 0.81128(9) 0.79488(18) 0.57878(9) 0.0376(4) Uani d . . . 1 . .
H H12 0.7902 0.8989 0.5814 0.045 Uiso calc U . R 1 . .
C C2 1.02063(9) 0.46874(18) 0.82383(9) 0.0371(4) Uani d . . . 1 . .
H H2 1.0746 0.503 0.8417 0.045 Uiso calc U . R 1 . .
C C3 0.97671(9) 0.52036(17) 0.76071(8) 0.0344(3) Uani d . . . 1 . .
H H3 0.9943 0.5974 0.7265 0.041 Uiso calc U . R 1 . .
C C13 0.84533(10) 0.74587(19) 0.51346(9) 0.0401(4) Uani d . . . 1 . .
C C29 0.57140(10) -0.00841(18) 0.77677(8) 0.0377(4) Uani d . . . 1 . .
H H29 0.5438 -0.0808 0.8073 0.045 Uiso calc U . R 1 . .
C C14 0.87551(10) 0.5941(2) 0.51054(8) 0.0390(4) Uani d . . . 1 . .
H H14 0.8991 0.5589 0.466 0.047 Uiso calc U . R 1 . .
C C25 0.44043(9) 0.11266(19) 0.57245(9) 0.0392(4) Uani d . . . 1 . .
C C31 0.68612(11) -0.0159(2) 0.87615(9) 0.0448(4) Uani d . . . 1 . .
H H31A 0.6478 -0.0907 0.8978 0.067 Uiso calc U . R 1 . .
H H31B 0.6961 0.0726 0.9106 0.067 Uiso calc U . R 1 . .
H H31C 0.7392 -0.0684 0.868 0.067 Uiso calc U . R 1 . .
C C23 0.42806(11) 0.2409(2) 0.45208(10) 0.0508(4) Uani d . . . 1 . .
H H23 0.3964 0.265 0.4069 0.061 Uiso calc U . R 1 . .
C C24 0.39605(10) 0.1475(2) 0.50413(10) 0.0480(4) Uani d . . . 1 . .
H H24 0.3419 0.1039 0.4944 0.058 Uiso calc U . R 1 . .
C C18 0.90586(12) 0.3270(2) 0.56483(9) 0.0479(4) Uani d . . . 1 . .
H H18A 0.9461 0.3065 0.6072 0.072 Uiso calc U . R 1 . .
H H18B 0.9336 0.3155 0.5177 0.072 Uiso calc U . R 1 . .
H H18C 0.8596 0.2519 0.5658 0.072 Uiso calc U . R 1 . .
C C16 0.76999(12) 0.7568(2) 0.71092(10) 0.0506(4) Uani d . . . 1 . .
H H16A 0.815 0.7772 0.7492 0.076 Uiso calc U . R 1 . .
H H16B 0.7319 0.6776 0.7294 0.076 Uiso calc U . R 1 . .
H H16C 0.7391 0.8543 0.6999 0.076 Uiso calc U . R 1 . .
C C21 0.55326(11) 0.2697(2) 0.53121(10) 0.0513(5) Uani d . . . 1 . .
H H21 0.6079 0.312 0.5387 0.062 Uiso calc U . R 1 . .
C C27 0.44788(11) -0.0251(2) 0.68990(10) 0.0537(5) Uani d . . . 1 . .
H H27 0.4234 -0.0943 0.7241 0.064 Uiso calc U . R 1 . .
B B1 0.82694(10) 0.22305(19) 0.83465(9) 0.0289(3) Uani d . . . 1 . .
C C26 0.40523(11) 0.0126(2) 0.62551(10) 0.0565(5) Uani d . . . 1 . .
H H26 0.3506 -0.0284 0.6154 0.068 Uiso calc U . R 1 . .
C C22 0.50783(13) 0.3012(2) 0.46557(10) 0.0601(5) Uani d . . . 1 . .
H H22 0.5313 0.3654 0.4288 0.072 Uiso calc U . R 1 . .
C C17 0.84938(14) 0.8544(3) 0.44702(11) 0.0658(6) Uani d . . . 1 . .
H H17A 0.7982 0.8435 0.4146 0.099 Uiso calc U . R 1 . .
H H17B 0.8978 0.8271 0.4187 0.099 Uiso calc U . R 1 . .
H H17C 0.8547 0.9632 0.4646 0.099 Uiso calc U . R 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F2 B1 . 1.3822(18) ?
F1 B1 . 1.3787(17) ?
N2 C9 . 1.3746(17) ?
N2 C6 . 1.3909(16) ?
N2 B1 . 1.5537(19) ?
N1 C1 . 1.3361(18) ?
N1 C4 . 1.3892(17) ?
N1 B1 . 1.558(2) ?
C6 C7 . 1.3894(19) ?
C6 C5 . 1.4023(19) ?
C8 C7 . 1.3982(18) ?
C8 C9 . 1.4405(19) ?
C8 C19 . 1.4459(19) ?
C5 C4 . 1.3814(19) ?
C5 C10 . 1.4923(18) ?
C4 C3 . 1.413(2) ?
C10 C11 . 1.397(2) ?
C10 C15 . 1.4004(19) ?
C7 H7 . 0.95 ?
C9 C30 . 1.4261(19) ?
C19 C28 . 1.403(2) ?
C19 C20 . 1.448(2) ?
C30 C29 . 1.361(2) ?
C30 C31 . 1.503(2) ?
C11 C12 . 1.387(2) ?
C11 C16 . 1.505(2) ?
C1 C2 . 1.396(2) ?
C1 H1 . 0.95 ?
C15 C14 . 1.386(2) ?
C15 C18 . 1.505(2) ?
C20 C21 . 1.401(2) ?
C20 C25 . 1.421(2) ?
C28 C27 . 1.422(2) ?
C28 C29 . 1.423(2) ?
C12 C13 . 1.382(2) ?
C12 H12 . 0.95 ?
C2 C3 . 1.366(2) ?
C2 H2 . 0.95 ?
C3 H3 . 0.95 ?
C13 C14 . 1.382(2) ?
C13 C17 . 1.509(2) ?
C29 H29 . 0.95 ?
C14 H14 . 0.95 ?
C25 C24 . 1.408(2) ?
C25 C26 . 1.417(2) ?
C31 H31A . 0.98 ?
C31 H31B . 0.98 ?
C31 H31C . 0.98 ?
C23 C24 . 1.348(3) ?
C23 C22 . 1.386(3) ?
C23 H23 . 0.95 ?
C24 H24 . 0.95 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
C21 C22 . 1.370(2) ?
C21 H21 . 0.95 ?
C27 C26 . 1.342(3) ?
C27 H27 . 0.95 ?
C26 H26 . 0.95 ?
C22 H22 . 0.95 ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 N2 C6 . . 106.55(11) ?
C9 N2 B1 . . 130.32(11) ?
C6 N2 B1 . . 123.12(11) ?
C1 N1 C4 . . 107.20(12) ?
C1 N1 B1 . . 126.88(12) ?
C4 N1 B1 . . 125.91(11) ?
C7 C6 N2 . . 110.03(11) ?
C7 C6 C5 . . 127.13(12) ?
N2 C6 C5 . . 122.84(12) ?
C7 C8 C9 . . 105.43(11) ?
C7 C8 C19 . . 133.21(13) ?
C9 C8 C19 . . 121.26(12) ?
C4 C5 C6 . . 120.40(12) ?
C4 C5 C10 . . 119.53(12) ?
C6 C5 C10 . . 120.06(12) ?
C5 C4 N1 . . 120.38(12) ?
C5 C4 C3 . . 131.44(13) ?
N1 C4 C3 . . 108.08(12) ?
C11 C10 C15 . . 120.82(13) ?
C11 C10 C5 . . 119.80(12) ?
C15 C10 C5 . . 119.38(12) ?
C6 C7 C8 . . 108.21(12) ?
C6 C7 H7 . . 125.9 ?
C8 C7 H7 . . 125.9 ?
N2 C9 C30 . . 128.53(12) ?
N2 C9 C8 . . 109.76(11) ?
C30 C9 C8 . . 121.67(12) ?
C28 C19 C8 . . 115.32(13) ?
C28 C19 C20 . . 118.74(13) ?
C8 C19 C20 . . 125.93(12) ?
C29 C30 C9 . . 115.05(13) ?
C29 C30 C31 . . 119.88(13) ?
C9 C30 C31 . . 125.07(13) ?
C12 C11 C10 . . 118.19(14) ?
C12 C11 C16 . . 120.47(14) ?
C10 C11 C16 . . 121.33(13) ?
N1 C1 C2 . . 110.42(12) ?
N1 C1 H1 . . 124.8 ?
C2 C1 H1 . . 124.8 ?
C14 C15 C10 . . 118.44(14) ?
C14 C15 C18 . . 120.27(14) ?
C10 C15 C18 . . 121.29(13) ?
C21 C20 C25 . . 116.51(14) ?
C21 C20 C19 . . 124.70(13) ?
C25 C20 C19 . . 118.77(13) ?
C19 C28 C27 . . 120.31(14) ?
C19 C28 C29 . . 121.10(13) ?
C27 C28 C29 . . 118.59(14) ?
C13 C12 C11 . . 122.38(14) ?
C13 C12 H12 . . 118.8 ?
C11 C12 H12 . . 118.8 ?
C3 C2 C1 . . 107.26(13) ?
C3 C2 H2 . . 126.4 ?
C1 C2 H2 . . 126.4 ?
C2 C3 C4 . . 107.02(13) ?
C2 C3 H3 . . 126.5 ?
C4 C3 H3 . . 126.5 ?
C14 C13 C12 . . 118.10(14) ?
C14 C13 C17 . . 120.75(16) ?
C12 C13 C17 . . 121.15(16) ?
C30 C29 C28 . . 125.50(13) ?
C30 C29 H29 . . 117.3 ?
C28 C29 H29 . . 117.3 ?
C13 C14 C15 . . 122.07(15) ?
C13 C14 H14 . . 119.0 ?
C15 C14 H14 . . 119.0 ?
C24 C25 C26 . . 120.41(15) ?
C24 C25 C20 . . 119.64(15) ?
C26 C25 C20 . . 119.95(15) ?
C30 C31 H31A . . 109.5 ?
C30 C31 H31B . . 109.5 ?
H31A C31 H31B . . 109.5 ?
C30 C31 H31C . . 109.5 ?
H31A C31 H31C . . 109.5 ?
H31B C31 H31C . . 109.5 ?
C24 C23 C22 . . 118.94(16) ?
C24 C23 H23 . . 120.5 ?
C22 C23 H23 . . 120.5 ?
C23 C24 C25 . . 121.93(15) ?
C23 C24 H24 . . 119.0 ?
C25 C24 H24 . . 119.0 ?
C15 C18 H18A . . 109.5 ?
C15 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C15 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C11 C16 H16A . . 109.5 ?
C11 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C11 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C22 C21 C20 . . 121.98(16) ?
C22 C21 H21 . . 119.0 ?
C20 C21 H21 . . 119.0 ?
C26 C27 C28 . . 121.17(16) ?
C26 C27 H27 . . 119.4 ?
C28 C27 H27 . . 119.4 ?
F1 B1 F2 . . 110.98(12) ?
F1 B1 N2 . . 111.13(12) ?
F2 B1 N2 . . 111.12(12) ?
F1 B1 N1 . . 108.57(12) ?
F2 B1 N1 . . 107.67(11) ?
N2 B1 N1 . . 107.20(11) ?
C27 C26 C25 . . 120.98(15) ?
C27 C26 H26 . . 119.5 ?
C25 C26 H26 . . 119.5 ?
C21 C22 C23 . . 120.95(18) ?
C21 C22 H22 . . 119.5 ?
C23 C22 H22 . . 119.5 ?
C13 C17 H17A . . 109.5 ?
C13 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C13 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N2 C6 C7 . . . . -0.89(14) ?
B1 N2 C6 C7 . . . . 179.31(12) ?
C9 N2 C6 C5 . . . . 179.28(12) ?
B1 N2 C6 C5 . . . . -0.51(19) ?
C7 C6 C5 C4 . . . . -177.60(13) ?
N2 C6 C5 C4 . . . . 2.2(2) ?
C7 C6 C5 C10 . . . . 1.3(2) ?
N2 C6 C5 C10 . . . . -178.90(12) ?
C6 C5 C4 N1 . . . . -0.4(2) ?
C10 C5 C4 N1 . . . . -179.29(12) ?
C6 C5 C4 C3 . . . . 175.70(14) ?
C10 C5 C4 C3 . . . . -3.2(2) ?
C1 N1 C4 C5 . . . . 176.56(12) ?
B1 N1 C4 C5 . . . . -3.2(2) ?
C1 N1 C4 C3 . . . . -0.36(15) ?
B1 N1 C4 C3 . . . . 179.91(12) ?
C4 C5 C10 C11 . . . . -87.78(16) ?
C6 C5 C10 C11 . . . . 93.31(16) ?
C4 C5 C10 C15 . . . . 91.54(16) ?
C6 C5 C10 C15 . . . . -87.37(16) ?
N2 C6 C7 C8 . . . . -0.02(15) ?
C5 C6 C7 C8 . . . . 179.80(13) ?
C9 C8 C7 C6 . . . . 0.87(14) ?
C19 C8 C7 C6 . . . . 177.10(14) ?
C6 N2 C9 C30 . . . . -176.34(13) ?
B1 N2 C9 C30 . . . . 3.4(2) ?
C6 N2 C9 C8 . . . . 1.45(14) ?
B1 N2 C9 C8 . . . . -178.78(12) ?
C7 C8 C9 N2 . . . . -1.46(14) ?
C19 C8 C9 N2 . . . . -178.24(11) ?
C7 C8 C9 C30 . . . . 176.51(12) ?
C19 C8 C9 C30 . . . . -0.27(19) ?
C7 C8 C19 C28 . . . . -172.88(14) ?
C9 C8 C19 C28 . . . . 2.86(18) ?
C7 C8 C19 C20 . . . . 6.2(2) ?
C9 C8 C19 C20 . . . . -178.10(12) ?
N2 C9 C30 C29 . . . . 175.80(13) ?
C8 C9 C30 C29 . . . . -1.8(2) ?
N2 C9 C30 C31 . . . . -3.9(2) ?
C8 C9 C30 C31 . . . . 178.58(13) ?
C15 C10 C11 C12 . . . . -0.1(2) ?
C5 C10 C11 C12 . . . . 179.23(12) ?
C15 C10 C11 C16 . . . . -179.41(14) ?
C5 C10 C11 C16 . . . . -0.1(2) ?
C4 N1 C1 C2 . . . . 0.22(16) ?
B1 N1 C1 C2 . . . . 179.96(13) ?
C11 C10 C15 C14 . . . . 0.2(2) ?
C5 C10 C15 C14 . . . . -179.15(12) ?
C11 C10 C15 C18 . . . . -179.73(14) ?
C5 C10 C15 C18 . . . . 1.0(2) ?
C28 C19 C20 C21 . . . . -175.59(15) ?
C8 C19 C20 C21 . . . . 5.4(2) ?
C28 C19 C20 C25 . . . . 2.9(2) ?
C8 C19 C20 C25 . . . . -176.07(13) ?
C8 C19 C28 C27 . . . . 176.41(14) ?
C20 C19 C28 C27 . . . . -2.7(2) ?
C8 C19 C28 C29 . . . . -3.5(2) ?
C20 C19 C28 C29 . . . . 177.42(13) ?
C10 C11 C12 C13 . . . . -0.1(2) ?
C16 C11 C12 C13 . . . . 179.27(14) ?
N1 C1 C2 C3 . . . . 0.00(17) ?
C1 C2 C3 C4 . . . . -0.22(17) ?
C5 C4 C3 C2 . . . . -176.09(15) ?
N1 C4 C3 C2 . . . . 0.36(16) ?
C11 C12 C13 C14 . . . . 0.1(2) ?
C11 C12 C13 C17 . . . . 179.96(15) ?
C9 C30 C29 C28 . . . . 1.2(2) ?
C31 C30 C29 C28 . . . . -179.14(15) ?
C19 C28 C29 C30 . . . . 1.6(2) ?
C27 C28 C29 C30 . . . . -178.33(16) ?
C12 C13 C14 C15 . . . . 0.0(2) ?
C17 C13 C14 C15 . . . . -179.88(15) ?
C10 C15 C14 C13 . . . . -0.1(2) ?
C18 C15 C14 C13 . . . . 179.79(15) ?
C21 C20 C25 C24 . . . . -1.6(2) ?
C19 C20 C25 C24 . . . . 179.73(14) ?
C21 C20 C25 C26 . . . . 177.56(16) ?
C19 C20 C25 C26 . . . . -1.1(2) ?
C22 C23 C24 C25 . . . . 1.6(3) ?
C26 C25 C24 C23 . . . . -179.29(17) ?
C20 C25 C24 C23 . . . . -0.1(3) ?
C25 C20 C21 C22 . . . . 1.9(3) ?
C19 C20 C21 C22 . . . . -179.50(17) ?
C19 C28 C27 C26 . . . . 0.5(3) ?
C29 C28 C27 C26 . . . . -179.59(18) ?
C9 N2 B1 F1 . . . . -63.62(18) ?
C6 N2 B1 F1 . . . . 116.12(14) ?
C9 N2 B1 F2 . . . . 60.49(18) ?
C6 N2 B1 F2 . . . . -119.78(13) ?
C9 N2 B1 N1 . . . . 177.88(12) ?
C6 N2 B1 N1 . . . . -2.38(17) ?
C1 N1 B1 F1 . . . . 64.44(17) ?
C4 N1 B1 F1 . . . . -115.87(14) ?
C1 N1 B1 F2 . . . . -55.78(18) ?
C4 N1 B1 F2 . . . . 123.91(13) ?
C1 N1 B1 N2 . . . . -175.41(12) ?
C4 N1 B1 N2 . . . . 4.27(18) ?
C28 C27 C26 C25 . . . . 1.4(3) ?
C24 C25 C26 C27 . . . . 178.06(18) ?
C20 C25 C26 C27 . . . . -1.1(3) ?
C20 C21 C22 C23 . . . . -0.5(3) ?
C24 C23 C22 C21 . . . . -1.3(3) ?



# start Validation Reply Form
_vrf_PLAT602_02817JorgeLabella   
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure ! Info
RESPONSE: The voids are filled with disordered solvent molecules, that 
could not be located in the electron density maps and 
included in the model
;
_vrf_RINTA01_02687JorgeLabella   
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: This value is due to the small size of the crystals. Unfortunately,
larger single crystals could not be obtained despite our best efforts.
;
_vrf_PLAT020_02687JorgeLabella   
;
PROBLEM: The Value of Rint is Greater Than 0.12 ......... 0.272 Report
RESPONSE: This value is due to the small size of the crystals. Unfortunately,
larger single crystals could not be obtained despite our best efforts.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_02814JorgeLabella
_database_code_depnum_ccdc_archive 'CCDC 1985330'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles'
;Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            JL376-26_250K
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H33 B F2 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         662.55

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   21.0905(5)
_cell_length_b                   18.9830(6)
_cell_length_c                   8.7486(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3502.60(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9280
_cell_measurement_theta_min      2.5635
_cell_measurement_theta_max      21.9697
_cell_measurement_temperature    250.(2)

_exptl_crystal_description       ribbon
_exptl_crystal_colour            'intense purple'
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.015
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1384

_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      250.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            81484
_diffrn_reflns_av_R_equivalents  0.0746
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10

_refine_special_details          
;
;

_reflns_number_total             3305
_reflns_number_gt                2298
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1780
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_number_reflns         3305
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1088P)²+0.7000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.237
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.75799(17) 0.75 -0.0478(4) 0.0378(8) Uani d T P S 1 . .
C C1 0.72583(10) 0.61840(11) -0.0520(2) 0.0374(5) Uani d . . . 1 . .
H H1 0.757 0.6035 -0.1218 0.045 Uiso calc U . R 1 . .
C C2 0.68362(9) 0.57287(11) 0.0243(2) 0.0360(5) Uani d . . . 1 . .
C C3 0.64669(10) 0.61621(10) 0.1163(2) 0.0359(5) Uani d . . . 1 . .
H H3 0.6143 0.6014 0.1828 0.043 Uiso calc U . R 1 . .
C C4 0.66630(10) 0.68636(10) 0.0925(2) 0.0347(5) Uani d . . . 1 . .
C C5 0.68045(10) 0.49655(11) -0.0026(3) 0.0389(6) Uani d . . . 1 . .
C C6 0.70015(12) 0.47019(12) -0.1431(3) 0.0505(6) Uani d . . . 1 . .
H H6 0.7169 0.5014 -0.2161 0.061 Uiso calc U . R 1 . .
C C7 0.69583(13) 0.39976(14) -0.1783(4) 0.0653(8) Uani d . . . 1 . .
H H7 0.7092 0.3834 -0.2744 0.078 Uiso calc U . R 1 . .
C C8 0.67189(14) 0.35352(14) -0.0724(4) 0.0767(10) Uani d . . . 1 . .
H H8 0.6682 0.3055 -0.097 0.092 Uiso calc U . R 1 . .
C C9 0.65332(13) 0.37678(13) 0.0690(4) 0.0632(8) Uani d . . . 1 . .
H H9 0.6381 0.3444 0.1416 0.076 Uiso calc U . R 1 . .
C C10 0.65688(10) 0.44861(12) 0.1061(3) 0.0444(6) Uani d . . . 1 . .
C C11 0.63653(11) 0.46918(12) 0.2551(3) 0.0492(6) Uani d . . . 1 . .
C C12 0.61773(12) 0.48163(14) 0.3817(3) 0.0542(7) Uani d . . . 1 . .
C C13 0.59234(13) 0.49837(15) 0.5290(3) 0.0574(7) Uani d . . . 1 . .
C C14 0.55974(14) 0.44780(19) 0.6128(3) 0.0706(8) Uani d . . . 1 . .
H H14 0.5558 0.4017 0.5745 0.085 Uiso calc U . R 1 . .
C C15 0.53334(15) 0.4649(3) 0.7514(4) 0.0887(12) Uani d . . . 1 . .
H H15 0.5117 0.4303 0.8077 0.106 Uiso calc U . R 1 . .
C C16 0.53826(18) 0.5320(3) 0.8086(4) 0.0928(12) Uani d . . . 1 . .
H H16 0.5196 0.5434 0.903 0.111 Uiso calc U . R 1 . .
C C17 0.5701(2) 0.5816(2) 0.7285(4) 0.0962(12) Uani d . . . 1 . .
H H17 0.5736 0.6275 0.7677 0.115 Uiso calc U . R 1 . .
C C18 0.59778(18) 0.56521(17) 0.5882(4) 0.0790(9) Uani d . . . 1 . .
H H18 0.6202 0.5999 0.534 0.095 Uiso calc U . R 1 . .
C C19 0.64249(13) 0.75 0.1478(3) 0.0324(7) Uani d T P S 1 . .
C C20 0.59219(13) 0.75 0.2679(3) 0.0331(7) Uani d T P S 1 . .
C C21 0.52772(14) 0.75 0.2278(4) 0.0422(8) Uani d T P S 1 . .
C C22 0.48326(16) 0.75 0.3437(4) 0.0502(9) Uani d T P S 1 . .
H H22 0.44 0.75 0.3177 0.06 Uiso calc U P R 1 . .
C C23 0.50001(16) 0.75 0.4975(4) 0.0482(9) Uani d T P S 1 . .
C C24 0.56375(16) 0.75 0.5325(4) 0.0451(8) Uani d T P S 1 . .
H H24 0.576 0.75 0.6358 0.054 Uiso calc U P R 1 . .
C C25 0.61036(14) 0.75 0.4210(4) 0.0399(7) Uani d T P S 1 . .
C C26 0.5072(2) 0.75 0.0641(5) 0.0666(12) Uani d T P S 1 . .
H H26A 0.466(3) 0.75 0.041(6) 0.105(18) Uiso d . P S 1 . .
H H26B 0.523(2) 0.784(2) 0.006(5) 0.127(16) Uiso d . . . 1 . .
C C27 0.4508(2) 0.75 0.6231(5) 0.0811(14) Uani d T P S 1 . .
H H27A 0.4647 0.7805 0.7055 0.122 Uiso calc U P R 0.5 . .
H H27B 0.4454 0.7025 0.6615 0.122 Uiso calc U P R 0.5 . .
H H27C 0.4108 0.7671 0.5829 0.122 Uiso calc U P R 0.5 . .
C C28 0.67901(19) 0.75 0.4670(6) 0.0689(13) Uani d T P S 1 . .
H H28A 0.690(3) 0.75 0.577(7) 0.113(18) Uiso d . P S 1 . .
H H28B 0.7015(19) 0.787(2) 0.420(5) 0.115(14) Uiso d . . . 1 . .
F F1 0.80922(9) 0.75 0.0521(3) 0.0583(6) Uani d T P S 1 . .
F F2 0.77823(10) 0.75 -0.1959(2) 0.0573(6) Uani d T P S 1 . .
N N1 0.71590(8) 0.68515(9) -0.0125(2) 0.0353(4) Uani d . . . 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 F2 . 1.364(4) ?
B1 F1 . 1.390(4) ?
B1 N1 7_575 1.549(3) ?
B1 N1 . 1.549(3) ?
C1 N1 . 1.330(3) ?
C1 C2 . 1.409(3) ?
C1 H1 . 0.94 ?
C2 C3 . 1.390(3) ?
C2 C5 . 1.469(3) ?
C3 C4 . 1.410(3) ?
C3 H3 . 0.94 ?
C4 N1 . 1.393(3) ?
C4 C19 . 1.395(2) ?
C5 C6 . 1.391(3) ?
C5 C10 . 1.407(3) ?
C6 C7 . 1.375(3) ?
C6 H6 . 0.94 ?
C7 C8 . 1.373(4) ?
C7 H7 . 0.94 ?
C8 C9 . 1.370(4) ?
C8 H8 . 0.94 ?
C9 C10 . 1.404(3) ?
C9 H9 . 0.94 ?
C10 C11 . 1.427(4) ?
C11 C12 . 1.200(4) ?
C12 C13 . 1.431(4) ?
C13 C18 . 1.375(4) ?
C13 C14 . 1.390(4) ?
C14 C15 . 1.373(5) ?
C14 H14 . 0.94 ?
C15 C16 . 1.371(5) ?
C15 H15 . 0.94 ?
C16 C17 . 1.353(5) ?
C16 H16 . 0.94 ?
C17 C18 . 1.394(5) ?
C17 H17 . 0.94 ?
C18 H18 . 0.94 ?
C19 C4 7_575 1.395(2) ?
C19 C20 . 1.493(4) ?
C20 C25 . 1.393(4) ?
C20 C21 . 1.404(4) ?
C21 C22 . 1.382(4) ?
C21 C26 . 1.496(5) ?
C22 C23 . 1.391(5) ?
C22 H22 . 0.94 ?
C23 C24 . 1.379(5) ?
C23 C27 . 1.511(5) ?
C24 C25 . 1.385(4) ?
C24 H24 . 0.94 ?
C25 C28 . 1.503(5) ?
C26 H26A . 0.90(6) ?
C26 H26B . 0.88(4) ?
C27 H27A . 0.97 ?
C27 H27B . 0.97 ?
C27 H27C . 0.97 ?
C28 H28A . 0.99(6) ?
C28 H28B . 0.94(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F2 B1 F1 . . 110.7(3) ?
F2 B1 N1 . 7_575 111.61(19) ?
F1 B1 N1 . 7_575 108.69(18) ?
F2 B1 N1 . . 111.62(19) ?
F1 B1 N1 . . 108.69(18) ?
N1 B1 N1 7_575 . 105.3(2) ?
N1 C1 C2 . . 111.22(18) ?
N1 C1 H1 . . 124.4 ?
C2 C1 H1 . . 124.4 ?
C3 C2 C1 . . 105.39(18) ?
C3 C2 C5 . . 130.62(19) ?
C1 C2 C5 . . 123.90(19) ?
C2 C3 C4 . . 108.01(18) ?
C2 C3 H3 . . 126.0 ?
C4 C3 H3 . . 126.0 ?
N1 C4 C19 . . 120.91(19) ?
N1 C4 C3 . . 107.59(17) ?
C19 C4 C3 . . 131.4(2) ?
C6 C5 C10 . . 118.0(2) ?
C6 C5 C2 . . 118.9(2) ?
C10 C5 C2 . . 123.1(2) ?
C7 C6 C5 . . 121.9(2) ?
C7 C6 H6 . . 119.1 ?
C5 C6 H6 . . 119.1 ?
C8 C7 C6 . . 119.7(3) ?
C8 C7 H7 . . 120.2 ?
C6 C7 H7 . . 120.2 ?
C9 C8 C7 . . 120.6(2) ?
C9 C8 H8 . . 119.7 ?
C7 C8 H8 . . 119.7 ?
C8 C9 C10 . . 120.4(3) ?
C8 C9 H9 . . 119.8 ?
C10 C9 H9 . . 119.8 ?
C9 C10 C5 . . 119.4(2) ?
C9 C10 C11 . . 117.4(2) ?
C5 C10 C11 . . 123.1(2) ?
C12 C11 C10 . . 175.2(3) ?
C11 C12 C13 . . 176.8(3) ?
C18 C13 C14 . . 118.6(3) ?
C18 C13 C12 . . 120.9(3) ?
C14 C13 C12 . . 120.4(3) ?
C15 C14 C13 . . 120.2(3) ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C16 C15 C14 . . 120.8(3) ?
C16 C15 H15 . . 119.6 ?
C14 C15 H15 . . 119.6 ?
C17 C16 C15 . . 119.6(3) ?
C17 C16 H16 . . 120.2 ?
C15 C16 H16 . . 120.2 ?
C16 C17 C18 . . 120.6(4) ?
C16 C17 H17 . . 119.7 ?
C18 C17 H17 . . 119.7 ?
C13 C18 C17 . . 120.2(3) ?
C13 C18 H18 . . 119.9 ?
C17 C18 H18 . . 119.9 ?
C4 C19 C4 . 7_575 120.0(3) ?
C4 C19 C20 . . 119.99(13) ?
C4 C19 C20 7_575 . 119.99(13) ?
C25 C20 C21 . . 120.5(3) ?
C25 C20 C19 . . 118.8(3) ?
C21 C20 C19 . . 120.8(3) ?
C22 C21 C20 . . 118.3(3) ?
C22 C21 C26 . . 120.5(3) ?
C20 C21 C26 . . 121.3(3) ?
C21 C22 C23 . . 122.5(3) ?
C21 C22 H22 . . 118.7 ?
C23 C22 H22 . . 118.7 ?
C24 C23 C22 . . 117.5(3) ?
C24 C23 C27 . . 120.5(3) ?
C22 C23 C27 . . 121.9(3) ?
C23 C24 C25 . . 122.4(3) ?
C23 C24 H24 . . 118.8 ?
C25 C24 H24 . . 118.8 ?
C24 C25 C20 . . 118.8(3) ?
C24 C25 C28 . . 119.7(3) ?
C20 C25 C28 . . 121.5(3) ?
C21 C26 H26A . . 120.(3) ?
C21 C26 H26B . . 116.(3) ?
H26A C26 H26B . . 104.(4) ?
C23 C27 H27A . . 109.5 ?
C23 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C23 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C25 C28 H28A . . 119.(3) ?
C25 C28 H28B . . 111.(3) ?
H28A C28 H28B . . 108.(3) ?
C1 N1 C4 . . 107.79(16) ?
C1 N1 B1 . . 127.99(18) ?
C4 N1 B1 . . 123.28(18) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . -0.6(2) ?
N1 C1 C2 C5 . . . . 176.2(2) ?
C1 C2 C3 C4 . . . . 0.9(2) ?
C5 C2 C3 C4 . . . . -175.6(2) ?
C2 C3 C4 N1 . . . . -0.9(2) ?
C2 C3 C4 C19 . . . . 175.2(2) ?
C3 C2 C5 C6 . . . . 150.4(2) ?
C1 C2 C5 C6 . . . . -25.5(3) ?
C3 C2 C5 C10 . . . . -28.0(4) ?
C1 C2 C5 C10 . . . . 156.1(2) ?
C10 C5 C6 C7 . . . . 1.4(4) ?
C2 C5 C6 C7 . . . . -177.1(2) ?
C5 C6 C7 C8 . . . . -0.4(4) ?
C6 C7 C8 C9 . . . . -1.2(5) ?
C7 C8 C9 C10 . . . . 1.8(5) ?
C8 C9 C10 C5 . . . . -0.8(4) ?
C8 C9 C10 C11 . . . . 179.8(3) ?
C6 C5 C10 C9 . . . . -0.8(3) ?
C2 C5 C10 C9 . . . . 177.6(2) ?
C6 C5 C10 C11 . . . . 178.6(2) ?
C2 C5 C10 C11 . . . . -2.9(3) ?
C18 C13 C14 C15 . . . . 0.4(4) ?
C12 C13 C14 C15 . . . . -177.5(3) ?
C13 C14 C15 C16 . . . . 0.5(5) ?
C14 C15 C16 C17 . . . . -0.8(5) ?
C15 C16 C17 C18 . . . . 0.2(6) ?
C14 C13 C18 C17 . . . . -1.0(5) ?
C12 C13 C18 C17 . . . . 176.8(3) ?
C16 C17 C18 C13 . . . . 0.8(5) ?
N1 C4 C19 C4 . . . 7_575 3.1(4) ?
C3 C4 C19 C4 . . . 7_575 -172.57(16) ?
N1 C4 C19 C20 . . . . -176.0(2) ?
C3 C4 C19 C20 . . . . 8.4(4) ?
C4 C19 C20 C25 . . . . 89.5(2) ?
C4 C19 C20 C25 7_575 . . . -89.5(2) ?
C4 C19 C20 C21 . . . . -90.5(2) ?
C4 C19 C20 C21 7_575 . . . 90.5(2) ?
C25 C20 C21 C22 . . . . 0 ?
C19 C20 C21 C22 . . . . 180.0 ?
C25 C20 C21 C26 . . . . 180.0 ?
C19 C20 C21 C26 . . . . 0 ?
C20 C21 C22 C23 . . . . 0.0000(10) ?
C26 C21 C22 C23 . . . . 180.0 ?
C21 C22 C23 C24 . . . . 0 ?
C21 C22 C23 C27 . . . . 180.0000(10) ?
C22 C23 C24 C25 . . . . 0.0000(10) ?
C27 C23 C24 C25 . . . . 180.0 ?
C23 C24 C25 C20 . . . . 0 ?
C23 C24 C25 C28 . . . . 180.0 ?
C21 C20 C25 C24 . . . . 0 ?
C19 C20 C25 C24 . . . . 180.0 ?
C21 C20 C25 C28 . . . . 180.0 ?
C19 C20 C25 C28 . . . . 0 ?
C2 C1 N1 C4 . . . . 0.0(2) ?
C2 C1 N1 B1 . . . . 169.0(2) ?
C19 C4 N1 C1 . . . . -176.0(2) ?
C3 C4 N1 C1 . . . . 0.5(2) ?
C19 C4 N1 B1 . . . . 14.3(4) ?
C3 C4 N1 B1 . . . . -169.1(2) ?
F2 B1 N1 C1 . . . . 44.5(4) ?
F1 B1 N1 C1 . . . . -77.9(3) ?
N1 B1 N1 C1 7_575 . . . 165.76(16) ?
F2 B1 N1 C4 . . . . -148.1(2) ?
F1 B1 N1 C4 . . . . 89.5(3) ?
N1 B1 N1 C4 7_575 . . . -26.8(4) ?


