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

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

data_3b
_database_code_depnum_ccdc_archive 'CCDC 2234859'
loop_
_audit_author_name
_audit_author_address
'Tiago Cruz'
;Centro de Quimica Estrutural, Instituto Superior Tecnico, Universidade de Lisboa
Portugal
;
_audit_update_record             
;
2023-01-06 deposited with the CCDC.	2023-03-10 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_3b                  
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The crystal presented poor diffracting power
;
_vrf_PLAT020_3b                  
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.248 Report
RESPONSE: The crystal presented poor diffracting power
;
_vrf_PLAT082_3b                  
;
PROBLEM: High R1 Value ..................................       0.17 Report
RESPONSE: The crystal presented poor diffracting power
;
_vrf_PLAT097_3b                  
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.08 eA-3
RESPONSE: The poor diffracting power of the crystal gave rise to positive residual density that did could not be attributed to any atom in the structure
;
# Added during the CSD deposition process: Friday 06 January 2023 04:07 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C42 H26 B2 F2 N2 O2'
_chemical_formula_sum            'C42 H26 B2 F2 N2 O2'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150
_chemical_formula_weight         650.27

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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'

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

_cell_length_a                   11.2348(6)
_cell_length_b                   14.9120(8)
_cell_length_c                   18.6487(10)
_cell_angle_alpha                90.000(2)
_cell_angle_beta                 92.236(2)
_cell_angle_gamma                90.000(2)
_cell_volume                     3121.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9956
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      28.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            187527
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_av_R_equivalents  0.2476
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.186
_diffrn_reflns_theta_max         30.173
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9198
_reflns_number_gt                6444
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    enCIFer
_computing_publication_material  ORTEP
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+22.3285P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9198
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2149
_refine_ls_R_factor_gt           0.1694
_refine_ls_wR_factor_ref         0.2953
_refine_ls_wR_factor_gt          0.2759
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.4925(3) 0.6276(2) 0.43060(18) 0.0393(8) Uani 1 1 d . . . . .
N1A N 0.2644(4) 0.2477(3) 0.6663(2) 0.0215(8) Uani 1 1 d . . . . .
O1 O -0.1103(4) 0.4171(3) 0.5151(2) 0.0386(10) Uani 1 1 d . . . . .
O1A O 0.4544(3) 0.1938(3) 0.7064(2) 0.0389(10) Uani 1 1 d . . . . .
C21A C 0.3281(4) 0.3124(3) 0.7006(2) 0.0234(10) Uani 1 1 d . . . . .
C21 C -0.2933(5) 0.4400(3) 0.4583(3) 0.0268(10) Uani 1 1 d . . . . .
N1 N -0.2751(4) 0.3502(3) 0.4500(3) 0.0371(11) Uani 1 1 d . . . . .
C19 C -0.1960(5) 0.5670(3) 0.5160(3) 0.0286(11) Uani 1 1 d . . . . .
H19 H -0.134018 0.594869 0.541881 0.034 Uiso 1 1 calc R U . . .
C18 C -0.2982(5) 0.6139(4) 0.4917(3) 0.0303(11) Uani 1 1 d . . . . .
H18 H -0.303459 0.674423 0.503096 0.036 Uiso 1 1 calc R U . . .
C13A C 0.1559(4) 0.2665(4) 0.6390(3) 0.0281(11) Uani 1 1 d . . . . .
H13A H 0.112256 0.222618 0.614272 0.034 Uiso 1 1 calc R U . . .
C6 C -0.0724(5) 0.1833(4) 0.5341(3) 0.0337(12) Uani 1 1 d . . . . .
C16A C 0.2865(5) 0.3993(4) 0.7107(3) 0.0312(12) Uani 1 1 d . . . . .
C16 C -0.3924(5) 0.4870(5) 0.4348(3) 0.0363(13) Uani 1 1 d . . . . .
C12 C -0.0590(5) 0.2786(4) 0.4320(3) 0.0300(11) Uani 1 1 d . . . . .
C20 C -0.1931(5) 0.4768(4) 0.4991(3) 0.0288(11) Uani 1 1 d . . . . .
C20A C 0.4398(5) 0.2803(4) 0.7236(3) 0.0321(12) Uani 1 1 d . . . . .
C7 C -0.0117(4) 0.2015(4) 0.4661(3) 0.0291(11) Uani 1 1 d . . . . .
C7A C 0.2503(5) 0.0100(4) 0.6504(3) 0.0295(11) Uani 1 1 d . . . . .
C1A C 0.3605(4) 0.1187(4) 0.5877(3) 0.0289(11) Uani 1 1 d . . . . .
C6A C 0.3018(5) 0.0356(4) 0.5813(3) 0.0294(11) Uani 1 1 d . . . . .
F1A F 0.3377(5) 0.5415(3) 0.7575(3) 0.0855(18) Uani 1 1 d . . . . .
B1A B 0.3437(5) 0.1577(4) 0.6672(3) 0.0269(12) Uani 1 1 d . . . . .
C4A C 0.3559(5) 0.0228(5) 0.4593(3) 0.0416(15) Uani 1 1 d . . . . .
H4A H 0.354482 -0.008791 0.416315 0.050 Uiso 1 1 calc R U . . .
C5A C 0.2994(5) -0.0125(4) 0.5177(3) 0.0342(12) Uani 1 1 d . . . . .
H5A H 0.260587 -0.067516 0.514203 0.041 Uiso 1 1 calc R U . . .
C8A C 0.1888(5) -0.0676(4) 0.6671(3) 0.0330(12) Uani 1 1 d . . . . .
H8A H 0.171006 -0.110011 0.631688 0.040 Uiso 1 1 calc R U . . .
C12A C 0.2750(5) 0.0760(3) 0.7034(3) 0.0274(11) Uani 1 1 d . . . . .
C14A C 0.1070(5) 0.3529(4) 0.6475(3) 0.0354(13) Uani 1 1 d . . . . .
H14A H 0.031151 0.365773 0.628610 0.043 Uiso 1 1 calc R U . . .
C19A C 0.5178(6) 0.3387(6) 0.7576(3) 0.052(2) Uani 1 1 d . . . . .
H19A H 0.594183 0.320700 0.772341 0.062 Uiso 1 1 calc R U . . .
C1 C -0.1551(6) 0.2502(4) 0.5473(3) 0.0378(13) Uani 1 1 d . . . . .
C15 C -0.4808(5) 0.4360(5) 0.3938(3) 0.0412(15) Uani 1 1 d . . . . .
H15 H -0.549144 0.463166 0.374281 0.049 Uiso 1 1 calc R U . . .
C2A C 0.4190(5) 0.1526(4) 0.5289(3) 0.0356(13) Uani 1 1 d . . . . .
H2A H 0.460589 0.206434 0.532431 0.043 Uiso 1 1 calc R U . . .
C17 C -0.3905(6) 0.5759(4) 0.4524(3) 0.0388(14) Uani 1 1 d . . . . .
C13 C -0.3523(6) 0.3028(4) 0.4127(3) 0.0410(15) Uani 1 1 d . . . . .
H13 H -0.339238 0.242294 0.403922 0.049 Uiso 1 1 calc R U . . .
C11A C 0.2390(5) 0.0613(4) 0.7729(3) 0.0370(13) Uani 1 1 d . . . . .
H11A H 0.255422 0.103928 0.808267 0.044 Uiso 1 1 calc R U . . .
C3A C 0.4140(5) 0.1037(4) 0.4638(3) 0.0377(13) Uani 1 1 d . . . . .
H3A H 0.450449 0.126601 0.423800 0.045 Uiso 1 1 calc R U . . .
C15A C 0.1706(6) 0.4166(4) 0.6831(3) 0.0386(14) Uani 1 1 d . . . . .
H15A H 0.137162 0.472983 0.689489 0.046 Uiso 1 1 calc R U . . .
C18A C 0.4785(7) 0.4261(6) 0.7693(4) 0.059(2) Uani 1 1 d . . . . .
H18A H 0.529190 0.465375 0.794351 0.071 Uiso 1 1 calc R U . . .
C14 C -0.4607(6) 0.3479(5) 0.3850(3) 0.0480(17) Uani 1 1 d . . . . .
H14 H -0.518222 0.313883 0.360195 0.058 Uiso 1 1 calc R U . . .
B1 B -0.1500(6) 0.3231(4) 0.4867(4) 0.0335(13) Uani 1 1 d . . . . .
C10 C 0.0723(7) 0.2529(5) 0.3352(3) 0.0523(18) Uani 1 1 d . . . . .
H10 H 0.100256 0.269637 0.290930 0.063 Uiso 1 1 calc R U . . .
C11 C -0.0170(6) 0.3020(4) 0.3662(3) 0.0405(14) Uani 1 1 d . . . . .
H11 H -0.049137 0.351534 0.342052 0.049 Uiso 1 1 calc R U . . .
C17A C 0.3723(8) 0.4560(5) 0.7464(4) 0.053(2) Uani 1 1 d . . . . .
C10A C 0.1784(6) -0.0172(5) 0.7899(3) 0.0430(15) Uani 1 1 d . . . . .
H10A H 0.154404 -0.026632 0.836481 0.052 Uiso 1 1 calc R U . . .
C9 C 0.1193(7) 0.1790(6) 0.3706(4) 0.061(2) Uani 1 1 d . . . . .
H9 H 0.178952 0.145936 0.349583 0.073 Uiso 1 1 calc R U . . .
C9A C 0.1540(6) -0.0815(4) 0.7369(3) 0.0416(14) Uani 1 1 d . . . . .
H9A H 0.114215 -0.133985 0.748365 0.050 Uiso 1 1 calc R U . . .
C8 C 0.0796(6) 0.1532(5) 0.4365(4) 0.0488(17) Uani 1 1 d . . . . .
H8 H 0.113388 0.104343 0.460712 0.059 Uiso 1 1 calc R U . . .
C5 C -0.0532(6) 0.1129(4) 0.5817(4) 0.0477(17) Uani 1 1 d . . . . .
H5 H 0.001895 0.068331 0.572086 0.057 Uiso 1 1 calc R U . . .
C4 C -0.1170(9) 0.1097(6) 0.6437(4) 0.073(3) Uani 1 1 d . . . . .
H4 H -0.104919 0.062897 0.676157 0.087 Uiso 1 1 calc R U . . .
C2 C -0.2185(8) 0.2452(5) 0.6097(4) 0.062(2) Uani 1 1 d . . . . .
H2 H -0.274649 0.289003 0.619144 0.074 Uiso 1 1 calc R U . . .
C3 C -0.1991(10) 0.1765(6) 0.6573(4) 0.079(3) Uani 1 1 d . . . . .
H3 H -0.241287 0.174515 0.699219 0.095 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C17 1.426(7) . ?
N1A C13A 1.332(6) . ?
N1A C21A 1.346(6) . ?
N1A B1A 1.611(7) . ?
O1 C20 1.313(7) . ?
O1 B1 1.557(8) . ?
O1A C20A 1.340(7) . ?
O1A B1A 1.517(7) . ?
C21A C16A 1.394(7) . ?
C21A C20A 1.395(7) . ?
C21 N1 1.364(7) . ?
C21 C16 1.373(8) . ?
C21 C20 1.442(7) . ?
N1 C13 1.298(7) . ?
N1 B1 1.592(8) . ?
C19 C20 1.382(7) . ?
C19 C18 1.404(8) . ?
C19 H19 0.9300 . ?
C18 C17 1.370(8) . ?
C18 H18 0.9300 . ?
C13A C14A 1.411(8) . ?
C13A H13A 0.9300 . ?
C6 C5 1.387(8) . ?
C6 C1 1.392(9) . ?
C6 C7 1.488(8) . ?
C16A C15A 1.405(9) . ?
C16A C17A 1.428(9) . ?
C16 C17 1.366(9) . ?
C16 C15 1.445(8) . ?
C12 C11 1.377(8) . ?
C12 C7 1.407(8) . ?
C12 B1 1.615(8) . ?
C20A C19A 1.374(8) . ?
C7 C8 1.385(8) . ?
C7A C8A 1.389(8) . ?
C7A C12A 1.416(7) . ?
C7A C6A 1.483(8) . ?
C1A C2A 1.395(8) . ?
C1A C6A 1.407(8) . ?
C1A B1A 1.611(8) . ?
C6A C5A 1.386(7) . ?
F1A C17A 1.351(8) . ?
B1A C12A 1.605(8) . ?
C4A C3A 1.373(9) . ?
C4A C5A 1.385(9) . ?
C4A H4A 0.9300 . ?
C5A H5A 0.9300 . ?
C8A C9A 1.389(9) . ?
C8A H8A 0.9300 . ?
C12A C11A 1.389(8) . ?
C14A C15A 1.348(9) . ?
C14A H14A 0.9300 . ?
C19A C18A 1.396(12) . ?
C19A H19A 0.9300 . ?
C1 C2 1.390(9) . ?
C1 B1 1.570(9) . ?
C15 C14 1.344(10) . ?
C15 H15 0.9300 . ?
C2A C3A 1.415(8) . ?
C2A H2A 0.9300 . ?
C13 C14 1.468(9) . ?
C13 H13 0.9300 . ?
C11A C10A 1.396(9) . ?
C11A H11A 0.9300 . ?
C3A H3A 0.9300 . ?
C15A H15A 0.9300 . ?
C18A C17A 1.328(12) . ?
C18A H18A 0.9300 . ?
C14 H14 0.9300 . ?
C10 C9 1.379(11) . ?
C10 C11 1.386(9) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C10A C9A 1.398(9) . ?
C10A H10A 0.9300 . ?
C9 C8 1.380(11) . ?
C9 H9 0.9300 . ?
C9A H9A 0.9300 . ?
C8 H8 0.9300 . ?
C5 C4 1.386(11) . ?
C5 H5 0.9300 . ?
C4 C3 1.387(13) . ?
C4 H4 0.9300 . ?
C2 C3 1.369(12) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13A N1A C21A 119.5(5) . . ?
C13A N1A B1A 132.6(4) . . ?
C21A N1A B1A 107.9(4) . . ?
C20 O1 B1 110.0(4) . . ?
C20A O1A B1A 110.5(4) . . ?
N1A C21A C16A 123.7(5) . . ?
N1A C21A C20A 110.8(5) . . ?
C16A C21A C20A 125.4(5) . . ?
N1 C21 C16 126.0(5) . . ?
N1 C21 C20 108.5(5) . . ?
C16 C21 C20 125.5(5) . . ?
C13 N1 C21 119.7(5) . . ?
C13 N1 B1 130.7(5) . . ?
C21 N1 B1 109.5(5) . . ?
C20 C19 C18 115.9(5) . . ?
C20 C19 H19 122.0 . . ?
C18 C19 H19 122.0 . . ?
C17 C18 C19 124.0(6) . . ?
C17 C18 H18 118.0 . . ?
C19 C18 H18 118.0 . . ?
N1A C13A C14A 120.2(5) . . ?
N1A C13A H13A 119.9 . . ?
C14A C13A H13A 119.9 . . ?
C5 C6 C1 121.2(6) . . ?
C5 C6 C7 128.2(6) . . ?
C1 C6 C7 110.5(5) . . ?
C21A C16A C15A 115.6(5) . . ?
C21A C16A C17A 113.0(6) . . ?
C15A C16A C17A 131.4(6) . . ?
C17 C16 C21 114.5(6) . . ?
C17 C16 C15 129.9(6) . . ?
C21 C16 C15 115.6(6) . . ?
C11 C12 C7 118.3(5) . . ?
C11 C12 B1 134.9(5) . . ?
C7 C12 B1 106.7(5) . . ?
O1 C20 C19 129.1(5) . . ?
O1 C20 C21 113.1(5) . . ?
C19 C20 C21 117.8(5) . . ?
O1A C20A C19A 129.7(6) . . ?
O1A C20A C21A 112.0(4) . . ?
C19A C20A C21A 118.3(6) . . ?
C8 C7 C12 121.2(6) . . ?
C8 C7 C6 127.9(6) . . ?
C12 C7 C6 110.9(5) . . ?
C8A C7A C12A 120.5(5) . . ?
C8A C7A C6A 128.6(5) . . ?
C12A C7A C6A 110.8(5) . . ?
C2A C1A C6A 119.1(5) . . ?
C2A C1A B1A 132.0(5) . . ?
C6A C1A B1A 108.9(5) . . ?
C5A C6A C1A 121.5(5) . . ?
C5A C6A C7A 128.0(5) . . ?
C1A C6A C7A 110.5(5) . . ?
O1A B1A C12A 117.7(4) . . ?
O1A B1A N1A 98.8(4) . . ?
C12A B1A N1A 111.2(4) . . ?
O1A B1A C1A 116.6(5) . . ?
C12A B1A C1A 100.9(4) . . ?
N1A B1A C1A 112.0(4) . . ?
C3A C4A C5A 121.2(6) . . ?
C3A C4A H4A 119.4 . . ?
C5A C4A H4A 119.4 . . ?
C6A C5A C4A 118.8(6) . . ?
C6A C5A H5A 120.6 . . ?
C4A C5A H5A 120.6 . . ?
C7A C8A C9A 119.7(5) . . ?
C7A C8A H8A 120.2 . . ?
C9A C8A H8A 120.2 . . ?
C11A C12A C7A 119.1(5) . . ?
C11A C12A B1A 132.4(5) . . ?
C7A C12A B1A 108.5(5) . . ?
C15A C14A C13A 119.9(5) . . ?
C15A C14A H14A 120.1 . . ?
C13A C14A H14A 120.1 . . ?
C20A C19A C18A 117.6(7) . . ?
C20A C19A H19A 121.2 . . ?
C18A C19A H19A 121.2 . . ?
C2 C1 C6 118.5(6) . . ?
C2 C1 B1 132.4(6) . . ?
C6 C1 B1 109.0(5) . . ?
C14 C15 C16 117.6(6) . . ?
C14 C15 H15 121.2 . . ?
C16 C15 H15 121.2 . . ?
C1A C2A C3A 118.9(6) . . ?
C1A C2A H2A 120.5 . . ?
C3A C2A H2A 120.5 . . ?
C16 C17 C18 122.3(6) . . ?
C16 C17 F1 116.8(5) . . ?
C18 C17 F1 120.8(6) . . ?
N1 C13 C14 117.8(6) . . ?
N1 C13 H13 121.1 . . ?
C14 C13 H13 121.1 . . ?
C12A C11A C10A 120.4(6) . . ?
C12A C11A H11A 119.8 . . ?
C10A C11A H11A 119.8 . . ?
C4A C3A C2A 120.5(6) . . ?
C4A C3A H3A 119.7 . . ?
C2A C3A H3A 119.7 . . ?
C14A C15A C16A 121.1(5) . . ?
C14A C15A H15A 119.5 . . ?
C16A C15A H15A 119.5 . . ?
C17A C18A C19A 123.3(6) . . ?
C17A C18A H18A 118.3 . . ?
C19A C18A H18A 118.3 . . ?
C15 C14 C13 123.0(5) . . ?
C15 C14 H14 118.5 . . ?
C13 C14 H14 118.5 . . ?
O1 B1 C1 113.4(5) . . ?
O1 B1 N1 98.9(4) . . ?
C1 B1 N1 115.3(5) . . ?
O1 B1 C12 113.9(5) . . ?
C1 B1 C12 102.2(5) . . ?
N1 B1 C12 113.8(5) . . ?
C9 C10 C11 119.6(6) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 121.0(6) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C18A C17A F1A 121.9(7) . . ?
C18A C17A C16A 122.2(7) . . ?
F1A C17A C16A 115.9(7) . . ?
C11A C10A C9A 119.9(6) . . ?
C11A C10A H10A 120.1 . . ?
C9A C10A H10A 120.1 . . ?
C10 C9 C8 121.1(7) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C8A C9A C10A 120.4(6) . . ?
C8A C9A H9A 119.8 . . ?
C10A C9A H9A 119.8 . . ?
C9 C8 C7 118.7(7) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C4 C5 C6 119.2(7) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C3 C4 C5 119.8(7) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C3 C2 C1 120.7(8) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.6(8) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13A N1A C21A C16A 1.1(7) . . . . ?
B1A N1A C21A C16A -179.3(4) . . . . ?
C13A N1A C21A C20A -178.5(4) . . . . ?
B1A N1A C21A C20A 1.1(5) . . . . ?
C16 C21 N1 C13 4.8(9) . . . . ?
C20 C21 N1 C13 -177.7(5) . . . . ?
C16 C21 N1 B1 -178.8(5) . . . . ?
C20 C21 N1 B1 -1.4(6) . . . . ?
C20 C19 C18 C17 -1.2(8) . . . . ?
C21A N1A C13A C14A -1.6(7) . . . . ?
B1A N1A C13A C14A 178.9(5) . . . . ?
N1A C21A C16A C15A 0.6(7) . . . . ?
C20A C21A C16A C15A -179.8(5) . . . . ?
N1A C21A C16A C17A -178.0(5) . . . . ?
C20A C21A C16A C17A 1.6(7) . . . . ?
N1 C21 C16 C17 177.6(5) . . . . ?
C20 C21 C16 C17 0.6(8) . . . . ?
N1 C21 C16 C15 -3.9(8) . . . . ?
C20 C21 C16 C15 179.1(5) . . . . ?
B1 O1 C20 C19 177.7(5) . . . . ?
B1 O1 C20 C21 -2.1(6) . . . . ?
C18 C19 C20 O1 -179.4(5) . . . . ?
C18 C19 C20 C21 0.4(7) . . . . ?
N1 C21 C20 O1 2.2(6) . . . . ?
C16 C21 C20 O1 179.7(5) . . . . ?
N1 C21 C20 C19 -177.5(5) . . . . ?
C16 C21 C20 C19 -0.1(8) . . . . ?
B1A O1A C20A C19A -178.5(6) . . . . ?
B1A O1A C20A C21A -0.2(6) . . . . ?
N1A C21A C20A O1A -0.6(6) . . . . ?
C16A C21A C20A O1A 179.7(5) . . . . ?
N1A C21A C20A C19A 177.9(5) . . . . ?
C16A C21A C20A C19A -1.7(8) . . . . ?
C11 C12 C7 C8 3.9(8) . . . . ?
B1 C12 C7 C8 -172.8(5) . . . . ?
C11 C12 C7 C6 -176.4(5) . . . . ?
B1 C12 C7 C6 6.9(6) . . . . ?
C5 C6 C7 C8 -1.9(9) . . . . ?
C1 C6 C7 C8 176.6(6) . . . . ?
C5 C6 C7 C12 178.4(5) . . . . ?
C1 C6 C7 C12 -3.1(6) . . . . ?
C2A C1A C6A C5A -0.9(8) . . . . ?
B1A C1A C6A C5A 178.6(5) . . . . ?
C2A C1A C6A C7A 177.5(5) . . . . ?
B1A C1A C6A C7A -3.0(6) . . . . ?
C8A C7A C6A C5A 0.2(9) . . . . ?
C12A C7A C6A C5A 178.0(5) . . . . ?
C8A C7A C6A C1A -178.0(5) . . . . ?
C12A C7A C6A C1A -0.2(6) . . . . ?
C20A O1A B1A C12A -119.0(5) . . . . ?
C20A O1A B1A N1A 0.7(5) . . . . ?
C20A O1A B1A C1A 120.9(5) . . . . ?
C13A N1A B1A O1A 178.5(5) . . . . ?
C21A N1A B1A O1A -1.1(5) . . . . ?
C13A N1A B1A C12A -57.1(7) . . . . ?
C21A N1A B1A C12A 123.3(4) . . . . ?
C13A N1A B1A C1A 55.0(7) . . . . ?
C21A N1A B1A C1A -124.6(5) . . . . ?
C2A C1A B1A O1A -47.1(8) . . . . ?
C6A C1A B1A O1A 133.4(5) . . . . ?
C2A C1A B1A C12A -175.9(5) . . . . ?
C6A C1A B1A C12A 4.6(5) . . . . ?
C2A C1A B1A N1A 65.6(7) . . . . ?
C6A C1A B1A N1A -113.8(5) . . . . ?
C1A C6A C5A C4A -0.3(8) . . . . ?
C7A C6A C5A C4A -178.4(5) . . . . ?
C3A C4A C5A C6A 0.3(8) . . . . ?
C12A C7A C8A C9A -1.7(8) . . . . ?
C6A C7A C8A C9A 175.9(5) . . . . ?
C8A C7A C12A C11A 1.4(7) . . . . ?
C6A C7A C12A C11A -176.7(5) . . . . ?
C8A C7A C12A B1A -178.7(5) . . . . ?
C6A C7A C12A B1A 3.3(6) . . . . ?
O1A B1A C12A C11A 47.2(8) . . . . ?
N1A B1A C12A C11A -65.7(7) . . . . ?
C1A B1A C12A C11A 175.3(5) . . . . ?
O1A B1A C12A C7A -132.8(5) . . . . ?
N1A B1A C12A C7A 114.3(4) . . . . ?
C1A B1A C12A C7A -4.7(5) . . . . ?
N1A C13A C14A C15A 0.3(8) . . . . ?
O1A C20A C19A C18A -179.5(6) . . . . ?
C21A C20A C19A C18A 2.2(8) . . . . ?
C5 C6 C1 C2 0.1(9) . . . . ?
C7 C6 C1 C2 -178.5(6) . . . . ?
C5 C6 C1 B1 176.2(5) . . . . ?
C7 C6 C1 B1 -2.4(6) . . . . ?
C17 C16 C15 C14 -179.3(6) . . . . ?
C21 C16 C15 C14 2.5(8) . . . . ?
C6A C1A C2A C3A 2.1(8) . . . . ?
B1A C1A C2A C3A -177.3(5) . . . . ?
C21 C16 C17 C18 -1.4(8) . . . . ?
C15 C16 C17 C18 -179.6(6) . . . . ?
C21 C16 C17 F1 -178.7(5) . . . . ?
C15 C16 C17 F1 3.1(9) . . . . ?
C19 C18 C17 C16 1.8(9) . . . . ?
C19 C18 C17 F1 179.0(5) . . . . ?
C21 N1 C13 C14 -4.0(9) . . . . ?
B1 N1 C13 C14 -179.4(6) . . . . ?
C7A C12A C11A C10A -0.6(8) . . . . ?
B1A C12A C11A C10A 179.4(6) . . . . ?
C5A C4A C3A C2A 0.9(9) . . . . ?
C1A C2A C3A C4A -2.1(8) . . . . ?
C13A C14A C15A C16A 1.5(8) . . . . ?
C21A C16A C15A C14A -1.9(8) . . . . ?
C17A C16A C15A C14A 176.4(6) . . . . ?
C20A C19A C18A C17A -3.1(10) . . . . ?
C16 C15 C14 C13 -2.2(10) . . . . ?
N1 C13 C14 C15 3.0(10) . . . . ?
C20 O1 B1 C1 -121.6(5) . . . . ?
C20 O1 B1 N1 1.1(6) . . . . ?
C20 O1 B1 C12 122.1(5) . . . . ?
C2 C1 B1 O1 58.5(9) . . . . ?
C6 C1 B1 O1 -116.9(5) . . . . ?
C2 C1 B1 N1 -54.5(9) . . . . ?
C6 C1 B1 N1 130.2(5) . . . . ?
C2 C1 B1 C12 -178.5(7) . . . . ?
C6 C1 B1 C12 6.2(6) . . . . ?
C13 N1 B1 O1 176.0(6) . . . . ?
C21 N1 B1 O1 0.3(6) . . . . ?
C13 N1 B1 C1 -62.8(9) . . . . ?
C21 N1 B1 C1 121.4(5) . . . . ?
C13 N1 B1 C12 55.0(9) . . . . ?
C21 N1 B1 C12 -120.8(5) . . . . ?
C11 C12 B1 O1 -61.0(9) . . . . ?
C7 C12 B1 O1 114.8(5) . . . . ?
C11 C12 B1 C1 176.3(6) . . . . ?
C7 C12 B1 C1 -7.8(6) . . . . ?
C11 C12 B1 N1 51.3(9) . . . . ?
C7 C12 B1 N1 -132.9(5) . . . . ?
C7 C12 C11 C10 -2.2(8) . . . . ?
B1 C12 C11 C10 173.2(6) . . . . ?
C9 C10 C11 C12 0.5(10) . . . . ?
C19A C18A C17A F1A -178.8(6) . . . . ?
C19A C18A C17A C16A 3.2(11) . . . . ?
C21A C16A C17A C18A -2.3(9) . . . . ?
C15A C16A C17A C18A 179.4(6) . . . . ?
C21A C16A C17A F1A 179.6(5) . . . . ?
C15A C16A C17A F1A 1.3(10) . . . . ?
C12A C11A C10A C9A 0.2(9) . . . . ?
C11 C10 C9 C8 -0.4(11) . . . . ?
C7A C8A C9A C10A 1.3(9) . . . . ?
C11A C10A C9A C8A -0.5(9) . . . . ?
C10 C9 C8 C7 1.9(11) . . . . ?
C12 C7 C8 C9 -3.7(9) . . . . ?
C6 C7 C8 C9 176.6(6) . . . . ?
C1 C6 C5 C4 -0.5(9) . . . . ?
C7 C6 C5 C4 177.9(6) . . . . ?
C6 C5 C4 C3 0.1(11) . . . . ?
C6 C1 C2 C3 0.6(11) . . . . ?
B1 C1 C2 C3 -174.4(7) . . . . ?
C1 C2 C3 C4 -1.0(13) . . . . ?
C5 C4 C3 C2 0.6(13) . . . . ?

_refine_diff_density_max         1.084
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.094

####################################################################### 
# 
# 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_3d
_database_code_depnum_ccdc_archive 'CCDC 2234861'
loop_
_audit_author_name
_audit_author_address
'Tiago Cruz'
;Centro de Quimica Estrutural, Instituto Superior Tecnico, Universidade de Lisboa
Portugal
;
_audit_update_record             
;
2023-01-06 deposited with the CCDC.	2023-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C21 H12 B Cl2 N O'
_chemical_formula_sum            'C21 H12 B Cl2 N O'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150
_chemical_formula_weight         376.03

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration ?

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'

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

_cell_length_a                   9.903(2)
_cell_length_b                   13.273(2)
_cell_length_c                   13.425(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.851(5)
_cell_angle_gamma                90
_cell_volume                     1713.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    1383
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      23.94
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.388
_shelx_estimated_absorpt_T_min   0.926
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7789
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.190
_diffrn_reflns_theta_max         25.821
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             3145
_reflns_number_gt                2187
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    enCIFer
_computing_publication_material  ORTEP
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0946P)²+0.0560P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3145
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1520
_refine_ls_wR_factor_gt          0.1282
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_restrained_S_all      0.921
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.8990(3) 0.2489(2) 0.5718(3) 0.0359(7) Uani 1 1 d . . . . .
C1 C 0.8134(3) 0.33221(19) 0.4953(2) 0.0355(6) Uani 1 1 d . . . . .
C2 C 0.7162(3) 0.4036(2) 0.5066(2) 0.0428(7) Uani 1 1 d . . . . .
H2 H 0.697688 0.413691 0.570585 0.051 Uiso 1 1 calc R U . . .
C3 C 0.6461(3) 0.4603(2) 0.4233(3) 0.0494(8) Uani 1 1 d . . . . .
H3 H 0.580774 0.507915 0.431493 0.059 Uiso 1 1 calc R U . . .
C4 C 0.6736(3) 0.4458(2) 0.3283(3) 0.0506(8) Uani 1 1 d . . . . .
H4 H 0.625459 0.483223 0.272469 0.061 Uiso 1 1 calc R U . . .
C5 C 0.7726(3) 0.3758(2) 0.3149(2) 0.0457(7) Uani 1 1 d . . . . .
H5 H 0.791589 0.366601 0.250919 0.055 Uiso 1 1 calc R U . . .
C6 C 0.8417(3) 0.32050(19) 0.3985(2) 0.0330(6) Uani 1 1 d . . . . .
C7 C 0.9456(3) 0.23976(19) 0.4014(2) 0.0355(6) Uani 1 1 d . . . . .
C8 C 0.9969(3) 0.2035(2) 0.3209(2) 0.0465(7) Uani 1 1 d . . . . .
H8 H 0.968218 0.231584 0.255812 0.056 Uiso 1 1 calc R U . . .
C9 C 1.0918(3) 0.1245(2) 0.3388(3) 0.0538(9) Uani 1 1 d . . . . .
H9 H 1.126310 0.099475 0.285037 0.065 Uiso 1 1 calc R U . . .
C10 C 1.1351(3) 0.0831(2) 0.4345(3) 0.0542(8) Uani 1 1 d . . . . .
H10 H 1.199901 0.031080 0.445879 0.065 Uiso 1 1 calc R U . . .
C11 C 1.0824(3) 0.1189(2) 0.5145(3) 0.0466(7) Uani 1 1 d . . . . .
H11 H 1.111202 0.089733 0.579054 0.056 Uiso 1 1 calc R U . . .
C12 C 0.9870(3) 0.19765(19) 0.4999(2) 0.0351(6) Uani 1 1 d . . . . .
C13 C 1.0873(3) 0.3593(2) 0.7063(2) 0.0383(6) Uani 1 1 d . . . . .
H13 H 1.126366 0.387307 0.656219 0.046 Uiso 1 1 calc R U . . .
C14 C 1.1365(3) 0.3867(2) 0.8084(2) 0.0416(7) Uani 1 1 d . . . . .
H14 H 1.209243 0.432671 0.825644 0.050 Uiso 1 1 calc R U . . .
C15 C 1.0813(3) 0.34837(19) 0.8842(2) 0.0393(7) Uani 1 1 d . . . . .
H15 H 1.115591 0.368019 0.952017 0.047 Uiso 1 1 calc R U . . .
C16 C 0.9713(3) 0.27842(19) 0.8581(2) 0.0340(6) Uani 1 1 d . . . . .
C17 C 0.8979(3) 0.2284(2) 0.9215(2) 0.0394(7) Uani 1 1 d . . . . .
C18 C 0.7947(3) 0.1607(2) 0.8823(2) 0.0424(7) Uani 1 1 d . . . . .
H18 H 0.747702 0.129560 0.926114 0.051 Uiso 1 1 calc R U . . .
C19 C 0.7581(3) 0.1372(2) 0.7767(2) 0.0365(6) Uani 1 1 d . . . . .
C20 C 0.8243(2) 0.18406(19) 0.7111(2) 0.0322(6) Uani 1 1 d . . . . .
C21 C 0.9289(3) 0.25294(18) 0.7544(2) 0.0308(6) Uani 1 1 d . . . . .
N1 N 0.9848(2) 0.29335(15) 0.68032(17) 0.0313(5) Uani 1 1 d . . . . .
O1 O 0.80583(18) 0.17449(13) 0.61035(14) 0.0379(5) Uani 1 1 d . . . . .
Cl1 Cl 0.93819(10) 0.25557(7) 1.05098(6) 0.0650(3) Uani 1 1 d . . . . .
Cl2 Cl 0.62782(8) 0.05048(6) 0.73136(7) 0.0528(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 O1 1.524(4) . ?
B1 C12 1.599(4) . ?
B1 C1 1.606(4) . ?
B1 N1 1.613(4) . ?
C1 C2 1.385(4) . ?
C1 C6 1.402(4) . ?
C2 C3 1.388(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.480(4) . ?
C7 C8 1.386(4) . ?
C7 C12 1.403(4) . ?
C8 C9 1.390(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.369(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.390(4) . ?
C11 H11 0.9300 . ?
C13 N1 1.322(3) . ?
C13 C14 1.389(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.363(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.410(4) . ?
C15 H15 0.9300 . ?
C16 C21 1.395(4) . ?
C16 C17 1.411(4) . ?
C17 C18 1.368(4) . ?
C17 Cl1 1.726(3) . ?
C18 C19 1.412(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.367(4) . ?
C19 Cl2 1.727(3) . ?
C20 O1 1.327(3) . ?
C20 C21 1.400(4) . ?
C21 N1 1.359(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 B1 C12 113.1(2) . . ?
O1 B1 C1 113.2(2) . . ?
C12 B1 C1 100.8(2) . . ?
O1 B1 N1 99.3(2) . . ?
C12 B1 N1 117.1(2) . . ?
C1 B1 N1 114.1(2) . . ?
C2 C1 C6 118.4(3) . . ?
C2 C1 B1 132.6(3) . . ?
C6 C1 B1 108.9(2) . . ?
C1 C2 C3 120.6(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 118.5(3) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 121.7(3) . . ?
C5 C6 C7 127.9(3) . . ?
C1 C6 C7 110.3(2) . . ?
C8 C7 C12 121.1(3) . . ?
C8 C7 C6 127.8(3) . . ?
C12 C7 C6 111.0(2) . . ?
C7 C8 C9 119.1(3) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.9(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C7 117.9(3) . . ?
C11 C12 B1 133.2(3) . . ?
C7 C12 B1 108.7(2) . . ?
N1 C13 C14 120.0(3) . . ?
N1 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 122.0(3) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C14 C15 C16 119.0(3) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C21 C16 C17 114.4(2) . . ?
C21 C16 C15 116.0(3) . . ?
C17 C16 C15 129.7(3) . . ?
C18 C17 C16 121.5(3) . . ?
C18 C17 Cl1 119.7(2) . . ?
C16 C17 Cl1 118.8(2) . . ?
C17 C18 C19 121.3(3) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C20 C19 C18 119.9(2) . . ?
C20 C19 Cl2 120.6(2) . . ?
C18 C19 Cl2 119.4(2) . . ?
O1 C20 C19 130.0(2) . . ?
O1 C20 C21 113.2(2) . . ?
C19 C20 C21 116.8(2) . . ?
N1 C21 C16 123.8(2) . . ?
N1 C21 C20 110.1(2) . . ?
C16 C21 C20 126.1(2) . . ?
C13 N1 C21 119.3(2) . . ?
C13 N1 B1 133.3(2) . . ?
C21 N1 B1 107.4(2) . . ?
C20 O1 B1 109.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 B1 C1 C2 58.6(4) . . . . ?
C12 B1 C1 C2 179.6(3) . . . . ?
N1 B1 C1 C2 -54.0(4) . . . . ?
O1 B1 C1 C6 -116.4(2) . . . . ?
C12 B1 C1 C6 4.6(3) . . . . ?
N1 B1 C1 C6 131.0(2) . . . . ?
C6 C1 C2 C3 1.6(4) . . . . ?
B1 C1 C2 C3 -173.0(3) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C4 C5 C6 C1 0.8(4) . . . . ?
C4 C5 C6 C7 177.2(2) . . . . ?
C2 C1 C6 C5 -1.9(4) . . . . ?
B1 C1 C6 C5 173.9(2) . . . . ?
C2 C1 C6 C7 -178.9(2) . . . . ?
B1 C1 C6 C7 -3.1(3) . . . . ?
C5 C6 C7 C8 0.9(4) . . . . ?
C1 C6 C7 C8 177.6(3) . . . . ?
C5 C6 C7 C12 -176.8(3) . . . . ?
C1 C6 C7 C12 -0.1(3) . . . . ?
C12 C7 C8 C9 -0.5(4) . . . . ?
C6 C7 C8 C9 -178.1(2) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
C8 C9 C10 C11 1.1(5) . . . . ?
C9 C10 C11 C12 -1.0(5) . . . . ?
C10 C11 C12 C7 0.1(4) . . . . ?
C10 C11 C12 B1 174.0(3) . . . . ?
C8 C7 C12 C11 0.6(4) . . . . ?
C6 C7 C12 C11 178.6(2) . . . . ?
C8 C7 C12 B1 -174.7(2) . . . . ?
C6 C7 C12 B1 3.3(3) . . . . ?
O1 B1 C12 C11 -57.8(4) . . . . ?
C1 B1 C12 C11 -179.0(3) . . . . ?
N1 B1 C12 C11 56.6(4) . . . . ?
O1 B1 C12 C7 116.5(2) . . . . ?
C1 B1 C12 C7 -4.7(3) . . . . ?
N1 B1 C12 C7 -129.1(2) . . . . ?
N1 C13 C14 C15 -0.7(4) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C14 C15 C16 C21 0.9(4) . . . . ?
C14 C15 C16 C17 179.8(3) . . . . ?
C21 C16 C17 C18 0.2(4) . . . . ?
C15 C16 C17 C18 -178.7(3) . . . . ?
C21 C16 C17 Cl1 -178.64(19) . . . . ?
C15 C16 C17 Cl1 2.4(4) . . . . ?
C16 C17 C18 C19 0.6(4) . . . . ?
Cl1 C17 C18 C19 179.5(2) . . . . ?
C17 C18 C19 C20 -1.4(4) . . . . ?
C17 C18 C19 Cl2 179.5(2) . . . . ?
C18 C19 C20 O1 -179.2(2) . . . . ?
Cl2 C19 C20 O1 -0.1(4) . . . . ?
C18 C19 C20 C21 1.2(4) . . . . ?
Cl2 C19 C20 C21 -179.75(19) . . . . ?
C17 C16 C21 N1 179.1(2) . . . . ?
C15 C16 C21 N1 -1.8(4) . . . . ?
C17 C16 C21 C20 -0.4(4) . . . . ?
C15 C16 C21 C20 178.7(2) . . . . ?
O1 C20 C21 N1 0.4(3) . . . . ?
C19 C20 C21 N1 -179.9(2) . . . . ?
O1 C20 C21 C16 180.0(2) . . . . ?
C19 C20 C21 C16 -0.3(4) . . . . ?
C14 C13 N1 C21 -0.1(4) . . . . ?
C14 C13 N1 B1 176.8(3) . . . . ?
C16 C21 N1 C13 1.4(4) . . . . ?
C20 C21 N1 C13 -179.0(2) . . . . ?
C16 C21 N1 B1 -176.2(2) . . . . ?
C20 C21 N1 B1 3.4(3) . . . . ?
O1 B1 N1 C13 177.5(2) . . . . ?
C12 B1 N1 C13 55.5(4) . . . . ?
C1 B1 N1 C13 -61.9(4) . . . . ?
O1 B1 N1 C21 -5.3(2) . . . . ?
C12 B1 N1 C21 -127.3(2) . . . . ?
C1 B1 N1 C21 115.3(2) . . . . ?
C19 C20 O1 B1 176.1(3) . . . . ?
C21 C20 O1 B1 -4.3(3) . . . . ?
C12 B1 O1 C20 130.4(2) . . . . ?
C1 B1 O1 C20 -115.7(2) . . . . ?
N1 B1 O1 C20 5.6(3) . . . . ?

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_3c
_database_code_depnum_ccdc_archive 'CCDC 2234860'
loop_
_audit_author_name
_audit_author_address
'Tiago Cruz'
;Centro de Quimica Estrutural, Instituto Superior Tecnico, Universidade de Lisboa
Portugal
;
_audit_update_record             
;
2023-01-06 deposited with the CCDC.	2023-03-10 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT026_3c                  
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        29% Check
RESPONSE: The crystal presented poor diffracting power and did not posess a suitable set of unique reflections
;
_vrf_RINTA01_3c                  
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The crystal presented poor diffracting power and did not posess a suitable set of unique reflections
;
_vrf_PLAT020_3c                  
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.191 Report
RESPONSE: The crystal presented poor diffracting power and did not posess a suitable set of unique reflections
;
_vrf_PLAT029_3c                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.947 Why?
RESPONSE: The crystal presented poor diffracting power and did not posess a suitable set of unique reflections
;
_vrf_PLAT340_3c                  
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01518 Ang.
RESPONSE: The crystal presented poor diffracting power and did not posess a suitable set of unique reflections
;
# Added during the CSD deposition process: Friday 06 January 2023 04:07 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C21 H13 B Cl N O'
_chemical_formula_sum            'C21 H13 B Cl N O'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150
_chemical_formula_weight         341.58

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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'

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

_cell_length_a                   15.216(12)
_cell_length_b                   7.888(6)
_cell_length_c                   13.809(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.18(2)
_cell_angle_gamma                90
_cell_volume                     1648(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    227
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      15.61
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.239
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5431
_diffrn_reflns_av_unetI/netI     0.3942
_diffrn_reflns_av_R_equivalents  0.1912
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.693
_diffrn_reflns_theta_max         25.646
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measured_fraction_theta_full 0.947
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_Laue_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_point_group_measured_fraction_full 0.947
_reflns_number_total             2943
_reflns_number_gt                849
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    enCIFer
_computing_publication_material  ORTEP
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0896P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2943
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3331
_refine_ls_R_factor_gt           0.1131
_refine_ls_wR_factor_ref         0.2928
_refine_ls_wR_factor_gt          0.2007
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_restrained_S_all      0.952
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.07552(18) 0.1750(3) 0.8956(2) 0.0518(10) Uani 1 1 d . . . . .
O1 O -0.1341(4) -0.4512(8) 0.8348(5) 0.0368(19) Uani 1 1 d . . . . .
N1 N -0.2081(5) -0.1905(10) 0.8640(6) 0.037(2) Uani 1 1 d . . . . .
C20 C -0.0777(6) -0.3174(13) 0.8447(6) 0.033(3) Uani 1 1 d . . . . .
C16 C -0.0783(6) -0.0056(12) 0.8758(7) 0.032(3) Uani 1 1 d . . . . .
C18 C 0.0574(7) -0.1626(13) 0.8600(7) 0.038(3) Uani 1 1 d . . . . .
H18 H 0.118400 -0.161342 0.859274 0.045 Uiso 1 1 calc R U . . .
C17 C 0.0163(7) -0.0135(14) 0.8758(7) 0.040(3) Uani 1 1 d . . . . .
C9 C -0.4720(7) -0.4673(14) 0.6526(9) 0.053(3) Uani 1 1 d . . . . .
H9 H -0.525511 -0.485602 0.614817 0.064 Uiso 1 1 calc R U . . .
C19 C 0.0129(6) -0.3199(14) 0.8446(7) 0.045(3) Uani 1 1 d . . . . .
H19 H 0.043257 -0.419770 0.834968 0.054 Uiso 1 1 calc R U . . .
C1 C -0.2660(6) -0.4749(11) 0.9421(8) 0.035(3) Uani 1 1 d . . . . .
C7 C -0.3785(7) -0.4878(12) 0.8081(8) 0.041(3) Uani 1 1 d . . . . .
C15 C -0.1345(7) 0.1300(12) 0.8925(8) 0.045(3) Uani 1 1 d . . . . .
H15 H -0.111315 0.238611 0.901880 0.054 Uiso 1 1 calc R U . . .
C6 C -0.3551(6) -0.5271(13) 0.9108(9) 0.040(3) Uani 1 1 d . . . . .
C2 C -0.2317(7) -0.5070(12) 1.0370(8) 0.042(3) Uani 1 1 d . . . . .
H2 H -0.174056 -0.474043 1.057698 0.050 Uiso 1 1 calc R U . . .
C8 C -0.4627(7) -0.5115(13) 0.7487(10) 0.052(3) Uani 1 1 d . . . . .
H8 H -0.510507 -0.557118 0.776484 0.062 Uiso 1 1 calc R U . . .
C21 C -0.1183(6) -0.1624(13) 0.8621(7) 0.034(3) Uani 1 1 d . . . . .
C13 C -0.2579(7) -0.0601(14) 0.8806(7) 0.048(3) Uani 1 1 d . . . . .
H13 H -0.318137 -0.076990 0.882962 0.058 Uiso 1 1 calc R U . . .
C12 C -0.3092(6) -0.4170(11) 0.7638(8) 0.031(3) Uani 1 1 d . . . . .
C10 C -0.4031(7) -0.3965(14) 0.6118(9) 0.056(3) Uani 1 1 d . . . . .
H10 H -0.411569 -0.360186 0.547410 0.067 Uiso 1 1 calc R U . . .
C4 C -0.3676(8) -0.6356(14) 1.0710(10) 0.062(4) Uani 1 1 d . . . . .
H4 H -0.401144 -0.690628 1.113859 0.075 Uiso 1 1 calc R U . . .
C11 C -0.3180(6) -0.3766(12) 0.6657(8) 0.043(3) Uani 1 1 d . . . . .
H11 H -0.270048 -0.337675 0.635623 0.051 Uiso 1 1 calc R U . . .
C14 C -0.2234(7) 0.1034(13) 0.8951(8) 0.050(3) Uani 1 1 d . . . . .
H14 H -0.260354 0.193436 0.906307 0.060 Uiso 1 1 calc R U . . .
B1 B -0.2267(7) -0.3902(14) 0.8507(9) 0.037(3) Uani 1 1 d . . . . .
C5 C -0.4035(7) -0.6018(14) 0.9763(9) 0.053(3) Uani 1 1 d . . . . .
H5 H -0.461995 -0.630861 0.957208 0.064 Uiso 1 1 calc R U . . .
C3 C -0.2808(8) -0.5868(14) 1.1017(8) 0.054(3) Uani 1 1 d . . . . .
H3 H -0.256447 -0.607996 1.165200 0.065 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C17 1.744(10) . ?
O1 C20 1.358(11) . ?
O1 B1 1.526(12) . ?
N1 C13 1.312(11) . ?
N1 C21 1.388(11) . ?
N1 B1 1.608(13) . ?
C20 C19 1.379(12) . ?
C20 C21 1.402(13) . ?
C16 C21 1.382(12) . ?
C16 C15 1.404(13) . ?
C16 C17 1.441(13) . ?
C18 C17 1.361(13) . ?
C18 C19 1.419(13) . ?
C18 H18 0.9300 . ?
C9 C10 1.362(14) . ?
C9 C8 1.365(14) . ?
C9 H9 0.9300 . ?
C19 H19 0.9300 . ?
C1 C2 1.380(13) . ?
C1 C6 1.439(12) . ?
C1 B1 1.600(16) . ?
C7 C12 1.391(12) . ?
C7 C8 1.457(13) . ?
C7 C6 1.458(14) . ?
C15 C14 1.373(13) . ?
C15 H15 0.9300 . ?
C6 C5 1.360(14) . ?
C2 C3 1.377(14) . ?
C2 H2 0.9300 . ?
C8 H8 0.9300 . ?
C13 C14 1.399(13) . ?
C13 H13 0.9300 . ?
C12 C11 1.385(13) . ?
C12 B1 1.654(14) . ?
C10 C11 1.430(13) . ?
C10 H10 0.9300 . ?
C4 C5 1.387(15) . ?
C4 C3 1.396(15) . ?
C4 H4 0.9300 . ?
C11 H11 0.9300 . ?
C14 H14 0.9300 . ?
C5 H5 0.9300 . ?
C3 H3 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O1 B1 108.9(7) . . ?
C13 N1 C21 117.8(9) . . ?
C13 N1 B1 133.7(9) . . ?
C21 N1 B1 108.4(8) . . ?
O1 C20 C19 127.5(10) . . ?
O1 C20 C21 114.2(8) . . ?
C19 C20 C21 118.1(9) . . ?
C21 C16 C15 116.0(9) . . ?
C21 C16 C17 112.7(9) . . ?
C15 C16 C17 131.2(10) . . ?
C17 C18 C19 124.1(10) . . ?
C17 C18 H18 118.0 . . ?
C19 C18 H18 118.0 . . ?
C18 C17 C16 120.9(9) . . ?
C18 C17 Cl1 121.6(8) . . ?
C16 C17 Cl1 117.6(8) . . ?
C10 C9 C8 120.2(10) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C20 C19 C18 116.6(10) . . ?
C20 C19 H19 121.7 . . ?
C18 C19 H19 121.7 . . ?
C2 C1 C6 118.7(10) . . ?
C2 C1 B1 133.6(9) . . ?
C6 C1 B1 107.6(9) . . ?
C12 C7 C8 117.8(10) . . ?
C12 C7 C6 113.3(10) . . ?
C8 C7 C6 128.9(10) . . ?
C14 C15 C16 120.4(9) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C5 C6 C1 118.9(11) . . ?
C5 C6 C7 130.2(10) . . ?
C1 C6 C7 110.8(9) . . ?
C3 C2 C1 121.6(10) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C9 C8 C7 120.4(11) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C16 C21 N1 124.1(9) . . ?
C16 C21 C20 127.5(9) . . ?
N1 C21 C20 108.5(9) . . ?
N1 C13 C14 122.2(10) . . ?
N1 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C11 C12 C7 121.6(9) . . ?
C11 C12 B1 131.8(9) . . ?
C7 C12 B1 106.6(9) . . ?
C9 C10 C11 121.6(11) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C5 C4 C3 119.8(11) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C12 C11 C10 118.1(10) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
C15 C14 C13 119.6(9) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
O1 B1 C1 114.3(9) . . ?
O1 B1 N1 99.9(8) . . ?
C1 B1 N1 113.3(9) . . ?
O1 B1 C12 119.7(9) . . ?
C1 B1 C12 101.5(8) . . ?
N1 B1 C12 108.5(8) . . ?
C6 C5 C4 121.6(11) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C2 C3 C4 119.4(11) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
B1 O1 C20 C19 173.7(10) . . . . ?
B1 O1 C20 C21 -2.5(11) . . . . ?
C19 C18 C17 C16 -1.4(15) . . . . ?
C19 C18 C17 Cl1 179.3(7) . . . . ?
C21 C16 C17 C18 2.2(14) . . . . ?
C15 C16 C17 C18 178.2(10) . . . . ?
C21 C16 C17 Cl1 -178.4(7) . . . . ?
C15 C16 C17 Cl1 -2.5(15) . . . . ?
O1 C20 C19 C18 -177.6(8) . . . . ?
C21 C20 C19 C18 -1.5(13) . . . . ?
C17 C18 C19 C20 1.0(15) . . . . ?
C21 C16 C15 C14 0.3(15) . . . . ?
C17 C16 C15 C14 -175.5(11) . . . . ?
C2 C1 C6 C5 1.9(14) . . . . ?
B1 C1 C6 C5 -179.3(9) . . . . ?
C2 C1 C6 C7 -178.0(9) . . . . ?
B1 C1 C6 C7 0.7(11) . . . . ?
C12 C7 C6 C5 -177.4(11) . . . . ?
C8 C7 C6 C5 3.3(18) . . . . ?
C12 C7 C6 C1 2.6(12) . . . . ?
C8 C7 C6 C1 -176.8(9) . . . . ?
C6 C1 C2 C3 -0.2(14) . . . . ?
B1 C1 C2 C3 -178.6(10) . . . . ?
C10 C9 C8 C7 -1.7(16) . . . . ?
C12 C7 C8 C9 0.9(14) . . . . ?
C6 C7 C8 C9 -179.7(10) . . . . ?
C15 C16 C21 N1 0.0(15) . . . . ?
C17 C16 C21 N1 176.6(9) . . . . ?
C15 C16 C21 C20 -179.7(9) . . . . ?
C17 C16 C21 C20 -3.1(15) . . . . ?
C13 N1 C21 C16 -0.6(14) . . . . ?
B1 N1 C21 C16 -177.0(9) . . . . ?
C13 N1 C21 C20 179.2(8) . . . . ?
B1 N1 C21 C20 2.8(11) . . . . ?
O1 C20 C21 C16 179.5(9) . . . . ?
C19 C20 C21 C16 2.9(15) . . . . ?
O1 C20 C21 N1 -0.2(11) . . . . ?
C19 C20 C21 N1 -176.9(8) . . . . ?
C21 N1 C13 C14 0.8(15) . . . . ?
B1 N1 C13 C14 176.1(10) . . . . ?
C8 C7 C12 C11 -2.8(14) . . . . ?
C6 C7 C12 C11 177.8(8) . . . . ?
C8 C7 C12 B1 175.0(8) . . . . ?
C6 C7 C12 B1 -4.5(11) . . . . ?
C8 C9 C10 C11 4.2(17) . . . . ?
C7 C12 C11 C10 5.1(14) . . . . ?
B1 C12 C11 C10 -171.9(9) . . . . ?
C9 C10 C11 C12 -5.9(15) . . . . ?
C16 C15 C14 C13 -0.2(16) . . . . ?
N1 C13 C14 C15 -0.4(17) . . . . ?
C20 O1 B1 C1 -117.5(9) . . . . ?
C20 O1 B1 N1 3.7(10) . . . . ?
C20 O1 B1 C12 121.9(9) . . . . ?
C2 C1 B1 O1 45.1(15) . . . . ?
C6 C1 B1 O1 -133.4(8) . . . . ?
C2 C1 B1 N1 -68.4(14) . . . . ?
C6 C1 B1 N1 113.1(9) . . . . ?
C2 C1 B1 C12 175.4(10) . . . . ?
C6 C1 B1 C12 -3.1(10) . . . . ?
C13 N1 B1 O1 -179.6(9) . . . . ?
C21 N1 B1 O1 -3.9(10) . . . . ?
C13 N1 B1 C1 -57.6(14) . . . . ?
C21 N1 B1 C1 118.0(9) . . . . ?
C13 N1 B1 C12 54.3(14) . . . . ?
C21 N1 B1 C12 -130.1(8) . . . . ?
C11 C12 B1 O1 -51.3(14) . . . . ?
C7 C12 B1 O1 131.3(9) . . . . ?
C11 C12 B1 C1 -178.1(9) . . . . ?
C7 C12 B1 C1 4.5(9) . . . . ?
C11 C12 B1 N1 62.3(13) . . . . ?
C7 C12 B1 N1 -115.0(9) . . . . ?
C1 C6 C5 C4 -3.0(16) . . . . ?
C7 C6 C5 C4 176.9(10) . . . . ?
C3 C4 C5 C6 2.4(17) . . . . ?
C1 C2 C3 C4 -0.4(16) . . . . ?
C5 C4 C3 C2 -0.7(16) . . . . ?

_refine_diff_density_max         0.611
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.086

####################################################################### 
# 
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 2234862'
loop_
_audit_author_name
_audit_author_address
'Tiago Cruz'
;Centro de Quimica Estrutural, Instituto Superior Tecnico, Universidade de Lisboa
Portugal
;
_audit_update_record             
;
2023-01-06 deposited with the CCDC.	2023-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C42 H30 B2 F N2 O3'
_chemical_formula_sum            'C42 H30 B2 F N2 O3'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150
_chemical_formula_weight         651.30

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

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'

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

_cell_length_a                   10.8807(6)
_cell_length_b                   28.8313(15)
_cell_length_c                   11.2931(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.236(2)
_cell_angle_gamma                90
_cell_volume                     3230.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9814
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             1356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            198612
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.053
_diffrn_reflns_theta_max         27.269
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7197
_reflns_number_gt                6149
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    enCIFer
_computing_publication_material  ORTEP
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+3.5857P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7197
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1410
_refine_ls_wR_factor_gt          0.1347
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 1.13050(13) 0.54579(5) 0.62050(15) 0.0390(3) Uani 1 1 d . . . . .
O1 O 0.82432(15) 0.54924(5) 0.90260(14) 0.0250(3) Uani 1 1 d . . . . .
F1A F 0.32252(14) 0.69717(5) 0.43765(16) 0.0436(4) Uani 1 1 d . . . . .
O1A O 0.70349(14) 0.71851(5) 0.24127(14) 0.0224(3) Uani 1 1 d . . . . .
N1 N 0.71509(17) 0.55119(6) 0.67014(16) 0.0212(3) Uani 1 1 d . . . . .
N1A N 0.77126(16) 0.69222(5) 0.46061(16) 0.0179(3) Uani 1 1 d . . . . .
C18 C 1.1228(2) 0.54572(8) 0.8283(2) 0.0317(5) Uani 1 1 d . . . . .
H18 H 1.216421 0.544009 0.866965 0.038 Uiso 1 1 calc R U . . .
C19 C 1.0517(2) 0.54619(7) 0.9092(2) 0.0269(5) Uani 1 1 d . . . . .
H19 H 1.097019 0.545038 0.999168 0.032 Uiso 1 1 calc R U . . .
C20 C 0.9136(2) 0.54842(7) 0.8501(2) 0.0233(4) Uani 1 1 d . . . . .
C12 C 0.62854(19) 0.49267(6) 0.79931(18) 0.0181(4) Uani 1 1 d . . . . .
C11 C 0.6662(2) 0.45543(7) 0.7426(2) 0.0234(4) Uani 1 1 d . . . . .
H11 H 0.709124 0.461359 0.687971 0.028 Uiso 1 1 calc R U . . .
C10 C 0.6416(2) 0.40985(7) 0.7654(2) 0.0289(5) Uani 1 1 d . . . . .
H10 H 0.669428 0.385767 0.727381 0.035 Uiso 1 1 calc R U . . .
C9 C 0.5756(2) 0.40004(7) 0.8445(2) 0.0286(5) Uani 1 1 d . . . . .
H9 H 0.559363 0.369474 0.860193 0.034 Uiso 1 1 calc R U . . .
C17 C 1.0594(2) 0.54766(8) 0.6960(2) 0.0295(5) Uani 1 1 d . . . . .
C8 C 0.5341(2) 0.43624(7) 0.8999(2) 0.0278(5) Uani 1 1 d . . . . .
H8 H 0.488879 0.430115 0.952441 0.033 Uiso 1 1 calc R U . . .
C7 C 0.5603(2) 0.48181(7) 0.8768(2) 0.0255(4) Uani 1 1 d . . . . .
H7 H 0.531413 0.505808 0.914222 0.031 Uiso 1 1 calc R U . . .
C1 C 0.5865(2) 0.58633(6) 0.80619(19) 0.0189(4) Uani 1 1 d . . . . .
C6 C 0.4466(2) 0.58658(7) 0.7336(2) 0.0258(4) Uani 1 1 d . . . . .
H6 H 0.406089 0.561833 0.678562 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3670(2) 0.62304(8) 0.7422(3) 0.0336(5) Uani 1 1 d . . . . .
H5 H 0.274458 0.622696 0.692464 0.040 Uiso 1 1 calc R U . . .
C4 C 0.4256(3) 0.65984(8) 0.8247(3) 0.0351(6) Uani 1 1 d . . . . .
H4 H 0.372373 0.684208 0.830543 0.042 Uiso 1 1 calc R U . . .
C3 C 0.5630(2) 0.66050(7) 0.8986(2) 0.0296(5) Uani 1 1 d . . . . .
H3 H 0.602255 0.685085 0.954769 0.035 Uiso 1 1 calc R U . . .
C2 C 0.6425(2) 0.62422(7) 0.8885(2) 0.0222(4) Uani 1 1 d . . . . .
H2 H 0.735078 0.625135 0.937645 0.027 Uiso 1 1 calc R U . . .
C13 C 0.6396(2) 0.55340(8) 0.5442(2) 0.0270(4) Uani 1 1 d . . . . .
H13 H 0.546214 0.553991 0.514007 0.032 Uiso 1 1 calc R U . . .
C14 C 0.7003(2) 0.55487(8) 0.4551(2) 0.0280(5) Uani 1 1 d . . . . .
H14 H 0.645768 0.556927 0.366814 0.034 Uiso 1 1 calc R U . . .
C15 C 0.8376(2) 0.55333(8) 0.4954(2) 0.0289(5) Uani 1 1 d . . . . .
H15 H 0.876280 0.553982 0.435711 0.035 Uiso 1 1 calc R U . . .
C16 C 0.9191(2) 0.55073(7) 0.6311(2) 0.0246(4) Uani 1 1 d . . . . .
C21 C 0.85056(19) 0.55036(6) 0.71238(18) 0.0178(4) Uani 1 1 d . . . . .
C4A C 1.0928(2) 0.83008(8) 0.4759(2) 0.0324(5) Uani 1 1 d . . . . .
H4A H 1.145645 0.856713 0.498487 0.039 Uiso 1 1 calc R U . . .
C3A C 1.0028(2) 0.82103(7) 0.5311(2) 0.0303(5) Uani 1 1 d . . . . .
H3A H 0.994962 0.841577 0.591115 0.036 Uiso 1 1 calc R U . . .
C2A C 0.9240(2) 0.78112(7) 0.4965(2) 0.0237(4) Uani 1 1 d . . . . .
H2A H 0.863935 0.775467 0.534251 0.028 Uiso 1 1 calc R U . . .
C1A C 0.93226(19) 0.74923(7) 0.40666(19) 0.0194(4) Uani 1 1 d . . . . .
C12A C 0.8973(2) 0.65852(7) 0.32490(19) 0.0191(4) Uani 1 1 d . . . . .
C11A C 0.8160(2) 0.62745(7) 0.22925(19) 0.0223(4) Uani 1 1 d . . . . .
H11A H 0.725137 0.634174 0.182931 0.027 Uiso 1 1 calc R U . . .
C10A C 0.8682(2) 0.58691(7) 0.2021(2) 0.0269(4) Uani 1 1 d . . . . .
H10A H 0.812150 0.566915 0.138119 0.032 Uiso 1 1 calc R U . . .
C9A C 1.0031(2) 0.57602(7) 0.2697(2) 0.0274(5) Uani 1 1 d . . . . .
H9A H 1.038298 0.549093 0.250485 0.033 Uiso 1 1 calc R U . . .
C17A C 0.4136(2) 0.70352(7) 0.3848(2) 0.0291(5) Uani 1 1 d . . . . .
C16A C 0.5500(2) 0.69323(7) 0.4643(2) 0.0236(4) Uani 1 1 d . . . . .
C21A C 0.63693(19) 0.70020(6) 0.4029(2) 0.0193(4) Uani 1 1 d . . . . .
C13A C 0.8261(2) 0.67718(7) 0.5820(2) 0.0213(4) Uani 1 1 d . . . . .
H13A H 0.918293 0.671584 0.621741 0.026 Uiso 1 1 calc R U . . .
C14A C 0.7463(2) 0.66956(7) 0.6516(2) 0.0249(4) Uani 1 1 d . . . . .
H14A H 0.786317 0.659314 0.737118 0.030 Uiso 1 1 calc R U . . .
C15A C 0.6093(2) 0.67715(7) 0.5939(2) 0.0263(5) Uani 1 1 d . . . . .
H15A H 0.556503 0.671760 0.639666 0.032 Uiso 1 1 calc R U . . .
C5A C 1.1035(2) 0.79915(8) 0.3868(2) 0.0316(5) Uani 1 1 d . . . . .
H5A H 1.163447 0.805135 0.349121 0.038 Uiso 1 1 calc R U . . .
C6A C 1.0253(2) 0.75929(7) 0.3536(2) 0.0258(4) Uani 1 1 d . . . . .
H6A H 1.034863 0.738684 0.294544 0.031 Uiso 1 1 calc R U . . .
C8A C 1.0853(2) 0.60574(8) 0.3666(2) 0.0277(5) Uani 1 1 d . . . . .
H8A H 1.175711 0.598455 0.413566 0.033 Uiso 1 1 calc R U . . .
C7A C 1.0329(2) 0.64635(7) 0.3935(2) 0.0237(4) Uani 1 1 d . . . . .
H7A H 1.089184 0.665925 0.458591 0.028 Uiso 1 1 calc R U . . .
C20A C 0.5986(2) 0.71577(7) 0.2742(2) 0.0216(4) Uani 1 1 d . . . . .
C19A C 0.4644(2) 0.72522(7) 0.2018(2) 0.0275(5) Uani 1 1 d . . . . .
H19A H 0.434565 0.735671 0.116619 0.033 Uiso 1 1 calc R U . . .
C18A C 0.3726(2) 0.71862(7) 0.2605(2) 0.0319(5) Uani 1 1 d . . . . .
H18A H 0.281632 0.724814 0.212340 0.038 Uiso 1 1 calc R U . . .
B1 B 0.6803(2) 0.54512(8) 0.7964(2) 0.0215(4) Uani 1 1 d . . . . .
B1A B 0.8342(2) 0.70489(7) 0.3560(2) 0.0186(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C17 1.367(3) . ?
O1 C20 1.330(3) . ?
O1 B1 1.538(3) . ?
F1A C17A 1.363(3) . ?
O1A C20A 1.340(2) . ?
O1A B1A 1.530(3) . ?
N1 C13 1.320(3) . ?
N1 C21 1.350(3) . ?
N1 B1 1.628(3) . ?
N1A C13A 1.324(3) . ?
N1A C21A 1.353(2) . ?
N1A B1A 1.631(3) . ?
C18 C17 1.366(3) . ?
C18 C19 1.420(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.420(3) . ?
C12 C11 1.395(3) . ?
C12 C7 1.396(3) . ?
C12 B1 1.619(3) . ?
C11 C10 1.386(3) . ?
C11 H11 0.9300 . ?
C10 C9 1.386(3) . ?
C10 H10 0.9300 . ?
C9 C8 1.384(3) . ?
C9 H9 0.9300 . ?
C17 C16 1.399(3) . ?
C8 C7 1.392(3) . ?
C8 H8 0.9300 . ?
C7 H7 0.9300 . ?
C1 C2 1.401(3) . ?
C1 C6 1.402(3) . ?
C1 B1 1.599(3) . ?
C6 C5 1.390(3) . ?
C6 H6 0.9300 . ?
C5 C4 1.383(4) . ?
C5 H5 0.9300 . ?
C4 C3 1.381(4) . ?
C4 H4 0.9300 . ?
C3 C2 1.391(3) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C13 C14 1.412(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.423(3) . ?
C15 H15 0.9300 . ?
C16 C21 1.400(3) . ?
C4A C5A 1.384(3) . ?
C4A C3A 1.385(3) . ?
C4A H4A 0.9300 . ?
C3A C2A 1.392(3) . ?
C3A H3A 0.9300 . ?
C2A C1A 1.399(3) . ?
C2A H2A 0.9300 . ?
C1A C6A 1.403(3) . ?
C1A B1A 1.612(3) . ?
C12A C7A 1.401(3) . ?
C12A C11A 1.402(3) . ?
C12A B1A 1.606(3) . ?
C11A C10A 1.387(3) . ?
C11A H11A 0.9300 . ?
C10A C9A 1.384(3) . ?
C10A H10A 0.9300 . ?
C9A C8A 1.388(3) . ?
C9A H9A 0.9300 . ?
C17A C18A 1.358(4) . ?
C17A C16A 1.415(3) . ?
C16A C21A 1.398(3) . ?
C16A C15A 1.414(3) . ?
C21A C20A 1.412(3) . ?
C13A C14A 1.407(3) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.377(3) . ?
C14A H14A 0.9300 . ?
C15A H15A 0.9300 . ?
C5A C6A 1.387(3) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
C8A C7A 1.390(3) . ?
C8A H8A 0.9300 . ?
C7A H7A 0.9300 . ?
C20A C19A 1.377(3) . ?
C19A C18A 1.420(3) . ?
C19A H19A 0.9300 . ?
C18A H18A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O1 B1 110.35(15) . . ?
C20A O1A B1A 110.55(15) . . ?
C13 N1 C21 119.18(18) . . ?
C13 N1 B1 133.13(18) . . ?
C21 N1 B1 107.52(16) . . ?
C13A N1A C21A 119.49(17) . . ?
C13A N1A B1A 132.76(16) . . ?
C21A N1A B1A 107.74(15) . . ?
C17 C18 C19 122.6(2) . . ?
C17 C18 H18 118.7 . . ?
C19 C18 H18 118.7 . . ?
C20 C19 C18 117.7(2) . . ?
C20 C19 H19 121.2 . . ?
C18 C19 H19 121.2 . . ?
O1 C20 C19 129.6(2) . . ?
O1 C20 C21 112.00(18) . . ?
C19 C20 C21 118.4(2) . . ?
C11 C12 C7 116.56(18) . . ?
C11 C12 B1 122.65(18) . . ?
C7 C12 B1 120.08(17) . . ?
C10 C11 C12 121.9(2) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C8 C9 C10 119.27(19) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
F1 C17 C18 121.3(2) . . ?
F1 C17 C16 116.8(2) . . ?
C18 C17 C16 121.9(2) . . ?
C9 C8 C7 119.8(2) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C7 C12 122.12(19) . . ?
C8 C7 H7 118.9 . . ?
C12 C7 H7 118.9 . . ?
C2 C1 C6 117.09(18) . . ?
C2 C1 B1 120.61(18) . . ?
C6 C1 B1 122.30(18) . . ?
C5 C6 C1 121.4(2) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C4 C5 C6 119.9(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C2 C1 121.7(2) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
N1 C13 C14 120.2(2) . . ?
N1 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 121.8(2) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C16 118.1(2) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
C21 C16 C17 114.6(2) . . ?
C21 C16 C15 116.26(19) . . ?
C17 C16 C15 129.1(2) . . ?
N1 C21 C16 124.47(18) . . ?
N1 C21 C20 110.76(17) . . ?
C16 C21 C20 124.77(19) . . ?
C5A C4A C3A 119.4(2) . . ?
C5A C4A H4A 120.3 . . ?
C3A C4A H4A 120.3 . . ?
C4A C3A C2A 119.8(2) . . ?
C4A C3A H3A 120.1 . . ?
C2A C3A H3A 120.1 . . ?
C3A C2A C1A 122.1(2) . . ?
C3A C2A H2A 118.9 . . ?
C1A C2A H2A 118.9 . . ?
C2A C1A C6A 116.52(19) . . ?
C2A C1A B1A 123.24(18) . . ?
C6A C1A B1A 120.08(18) . . ?
C7A C12A C11A 116.97(18) . . ?
C7A C12A B1A 122.38(17) . . ?
C11A C12A B1A 120.62(17) . . ?
C10A C11A C12A 121.52(19) . . ?
C10A C11A H11A 119.2 . . ?
C12A C11A H11A 119.2 . . ?
C9A C10A C11A 120.4(2) . . ?
C9A C10A H10A 119.8 . . ?
C11A C10A H10A 119.8 . . ?
C10A C9A C8A 119.27(19) . . ?
C10A C9A H9A 120.4 . . ?
C8A C9A H9A 120.4 . . ?
C18A C17A F1A 120.4(2) . . ?
C18A C17A C16A 122.5(2) . . ?
F1A C17A C16A 117.1(2) . . ?
C21A C16A C15A 116.50(19) . . ?
C21A C16A C17A 113.7(2) . . ?
C15A C16A C17A 129.8(2) . . ?
N1A C21A C16A 123.65(19) . . ?
N1A C21A C20A 110.70(17) . . ?
C16A C21A C20A 125.64(19) . . ?
N1A C13A C14A 120.71(19) . . ?
N1A C13A H13A 119.6 . . ?
C14A C13A H13A 119.6 . . ?
C15A C14A C13A 120.5(2) . . ?
C15A C14A H14A 119.8 . . ?
C13A C14A H14A 119.8 . . ?
C14A C15A C16A 119.16(19) . . ?
C14A C15A H15A 120.4 . . ?
C16A C15A H15A 120.4 . . ?
C4A C5A C6A 120.4(2) . . ?
C4A C5A H5A 119.8 . . ?
C6A C5A H5A 119.8 . . ?
C5A C6A C1A 121.7(2) . . ?
C5A C6A H6A 119.1 . . ?
C1A C6A H6A 119.1 . . ?
C7A C8A C9A 120.2(2) . . ?
C7A C8A H8A 119.9 . . ?
C9A C8A H8A 119.9 . . ?
C8A C7A C12A 121.61(19) . . ?
C8A C7A H7A 119.2 . . ?
C12A C7A H7A 119.2 . . ?
O1A C20A C19A 129.8(2) . . ?
O1A C20A C21A 112.31(17) . . ?
C19A C20A C21A 117.9(2) . . ?
C20A C19A C18A 118.3(2) . . ?
C20A C19A H19A 120.8 . . ?
C18A C19A H19A 120.8 . . ?
C17A C18A C19A 122.0(2) . . ?
C17A C18A H18A 119.0 . . ?
C19A C18A H18A 119.0 . . ?
O1 B1 C1 111.32(16) . . ?
O1 B1 C12 107.96(16) . . ?
C1 B1 C12 117.08(17) . . ?
O1 B1 N1 98.40(15) . . ?
C1 B1 N1 111.39(16) . . ?
C12 B1 N1 109.03(16) . . ?
O1A B1A C12A 111.12(16) . . ?
O1A B1A C1A 110.29(15) . . ?
C12A B1A C1A 117.21(16) . . ?
O1A B1A N1A 98.66(14) . . ?
C12A B1A N1A 108.42(15) . . ?
C1A B1A N1A 109.52(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 C18 C19 C20 0.4(3) . . . . ?
B1 O1 C20 C19 -172.2(2) . . . . ?
B1 O1 C20 C21 8.0(2) . . . . ?
C18 C19 C20 O1 179.9(2) . . . . ?
C18 C19 C20 C21 -0.3(3) . . . . ?
C7 C12 C11 C10 -2.2(3) . . . . ?
B1 C12 C11 C10 168.2(2) . . . . ?
C12 C11 C10 C9 1.2(3) . . . . ?
C11 C10 C9 C8 0.3(3) . . . . ?
C19 C18 C17 F1 -178.1(2) . . . . ?
C19 C18 C17 C16 0.6(3) . . . . ?
C10 C9 C8 C7 -0.7(3) . . . . ?
C9 C8 C7 C12 -0.4(3) . . . . ?
C11 C12 C7 C8 1.8(3) . . . . ?
B1 C12 C7 C8 -168.8(2) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
B1 C1 C6 C5 -179.1(2) . . . . ?
C1 C6 C5 C4 -0.7(3) . . . . ?
C6 C5 C4 C3 0.1(4) . . . . ?
C5 C4 C3 C2 0.7(3) . . . . ?
C4 C3 C2 C1 -0.9(3) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
B1 C1 C2 C3 179.93(19) . . . . ?
C21 N1 C13 C14 0.0(3) . . . . ?
B1 N1 C13 C14 -174.5(2) . . . . ?
N1 C13 C14 C15 1.0(3) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
F1 C17 C16 C21 177.15(18) . . . . ?
C18 C17 C16 C21 -1.6(3) . . . . ?
F1 C17 C16 C15 -1.7(3) . . . . ?
C18 C17 C16 C15 179.6(2) . . . . ?
C14 C15 C16 C21 -0.5(3) . . . . ?
C14 C15 C16 C17 178.3(2) . . . . ?
C13 N1 C21 C16 -1.4(3) . . . . ?
B1 N1 C21 C16 174.43(18) . . . . ?
C13 N1 C21 C20 179.43(18) . . . . ?
B1 N1 C21 C20 -4.8(2) . . . . ?
C17 C16 C21 N1 -177.36(18) . . . . ?
C15 C16 C21 N1 1.6(3) . . . . ?
C17 C16 C21 C20 1.7(3) . . . . ?
C15 C16 C21 C20 -179.28(19) . . . . ?
O1 C20 C21 N1 -1.8(2) . . . . ?
C19 C20 C21 N1 178.41(17) . . . . ?
O1 C20 C21 C16 179.02(18) . . . . ?
C19 C20 C21 C16 -0.8(3) . . . . ?
C5A C4A C3A C2A -0.1(3) . . . . ?
C4A C3A C2A C1A 0.0(3) . . . . ?
C3A C2A C1A C6A 0.5(3) . . . . ?
C3A C2A C1A B1A -174.92(19) . . . . ?
C7A C12A C11A C10A -1.1(3) . . . . ?
B1A C12A C11A C10A -179.12(19) . . . . ?
C12A C11A C10A C9A 0.1(3) . . . . ?
C11A C10A C9A C8A 1.1(3) . . . . ?
C18A C17A C16A C21A 0.1(3) . . . . ?
F1A C17A C16A C21A 179.45(17) . . . . ?
C18A C17A C16A C15A -179.6(2) . . . . ?
F1A C17A C16A C15A -0.3(3) . . . . ?
C13A N1A C21A C16A -0.3(3) . . . . ?
B1A N1A C21A C16A -179.76(17) . . . . ?
C13A N1A C21A C20A -179.73(17) . . . . ?
B1A N1A C21A C20A 0.8(2) . . . . ?
C15A C16A C21A N1A 0.3(3) . . . . ?
C17A C16A C21A N1A -179.53(18) . . . . ?
C15A C16A C21A C20A 179.61(18) . . . . ?
C17A C16A C21A C20A -0.2(3) . . . . ?
C21A N1A C13A C14A -0.2(3) . . . . ?
B1A N1A C13A C14A 179.09(18) . . . . ?
N1A C13A C14A C15A 0.7(3) . . . . ?
C13A C14A C15A C16A -0.7(3) . . . . ?
C21A C16A C15A C14A 0.2(3) . . . . ?
C17A C16A C15A C14A -180.0(2) . . . . ?
C3A C4A C5A C6A -0.4(3) . . . . ?
C4A C5A C6A C1A 0.9(3) . . . . ?
C2A C1A C6A C5A -1.0(3) . . . . ?
B1A C1A C6A C5A 174.6(2) . . . . ?
C10A C9A C8A C7A -1.1(3) . . . . ?
C9A C8A C7A C12A 0.0(3) . . . . ?
C11A C12A C7A C8A 1.1(3) . . . . ?
B1A C12A C7A C8A 179.02(19) . . . . ?
B1A O1A C20A C19A 179.3(2) . . . . ?
B1A O1A C20A C21A -1.4(2) . . . . ?
N1A C21A C20A O1A 0.3(2) . . . . ?
C16A C21A C20A O1A -179.06(17) . . . . ?
N1A C21A C20A C19A 179.66(17) . . . . ?
C16A C21A C20A C19A 0.3(3) . . . . ?
O1A C20A C19A C18A 178.95(19) . . . . ?
C21A C20A C19A C18A -0.2(3) . . . . ?
F1A C17A C18A C19A -179.42(18) . . . . ?
C16A C17A C18A C19A -0.1(3) . . . . ?
C20A C19A C18A C17A 0.2(3) . . . . ?
C20 O1 B1 C1 -126.62(17) . . . . ?
C20 O1 B1 C12 103.56(18) . . . . ?
C20 O1 B1 N1 -9.66(19) . . . . ?
C2 C1 B1 O1 10.3(3) . . . . ?
C6 C1 B1 O1 -170.06(17) . . . . ?
C2 C1 B1 C12 135.14(19) . . . . ?
C6 C1 B1 C12 -45.2(3) . . . . ?
C2 C1 B1 N1 -98.4(2) . . . . ?
C6 C1 B1 N1 81.2(2) . . . . ?
C11 C12 B1 O1 -79.5(2) . . . . ?
C7 C12 B1 O1 90.5(2) . . . . ?
C11 C12 B1 C1 154.01(19) . . . . ?
C7 C12 B1 C1 -36.0(3) . . . . ?
C11 C12 B1 N1 26.4(3) . . . . ?
C7 C12 B1 N1 -163.54(18) . . . . ?
C13 N1 B1 O1 -176.6(2) . . . . ?
C21 N1 B1 O1 8.47(19) . . . . ?
C13 N1 B1 C1 -59.7(3) . . . . ?
C21 N1 B1 C1 125.38(18) . . . . ?
C13 N1 B1 C12 71.1(3) . . . . ?
C21 N1 B1 C12 -103.90(18) . . . . ?
C20A O1A B1A C12A 115.39(17) . . . . ?
C20A O1A B1A C1A -112.90(17) . . . . ?
C20A O1A B1A N1A 1.72(18) . . . . ?
C7A C12A B1A O1A 160.18(18) . . . . ?
C11A C12A B1A O1A -22.0(2) . . . . ?
C7A C12A B1A C1A 32.1(3) . . . . ?
C11A C12A B1A C1A -150.03(18) . . . . ?
C7A C12A B1A N1A -92.4(2) . . . . ?
C11A C12A B1A N1A 85.4(2) . . . . ?
C2A C1A B1A O1A 85.7(2) . . . . ?
C6A C1A B1A O1A -89.6(2) . . . . ?
C2A C1A B1A C12A -145.82(19) . . . . ?
C6A C1A B1A C12A 38.9(3) . . . . ?
C2A C1A B1A N1A -21.8(3) . . . . ?
C6A C1A B1A N1A 162.88(17) . . . . ?
C13A N1A B1A O1A 179.16(19) . . . . ?
C21A N1A B1A O1A -1.50(18) . . . . ?
C13A N1A B1A C12A 63.4(3) . . . . ?
C21A N1A B1A C12A -117.27(17) . . . . ?
C13A N1A B1A C1A -65.6(3) . . . . ?
C21A N1A B1A C1A 113.72(17) . . . . ?

_refine_diff_density_max         0.741
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_4d
_database_code_depnum_ccdc_archive 'CCDC 2234863'
loop_
_audit_author_name
_audit_author_address
'Tiago Cruz'
;Centro de Quimica Estrutural, Instituto Superior Tecnico, Universidade de Lisboa
Portugal
;
_audit_update_record             
;
2023-01-06 deposited with the CCDC.	2023-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C21 H14 B Cl2 N O'
_chemical_formula_sum            'C21 H14 B Cl2 N O'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150
_chemical_formula_weight         378.04

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration ?

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'

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

_cell_length_a                   8.9037(7)
_cell_length_b                   17.9932(13)
_cell_length_c                   11.0787(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.586(4)
_cell_angle_gamma                90
_cell_volume                     1732.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    1912
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      25.48
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.384
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9992
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.259
_diffrn_reflns_theta_max         25.791
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3247
_reflns_number_gt                2330
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    enCIFer
_computing_publication_material  ORTEP
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0858P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3247
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   0.863
_refine_ls_restrained_S_all      0.863
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.8174(3) 0.20857(15) 1.3612(2) 0.0177(6) Uani 1 1 d . . . . .
C1 C 0.7478(3) 0.16375(13) 1.4609(2) 0.0167(5) Uani 1 1 d . . . . .
C2 C 0.7304(3) 0.08680(14) 1.4557(2) 0.0226(6) Uani 1 1 d . . . . .
H2 H 0.756724 0.060929 1.390587 0.027 Uiso 1 1 calc R U . . .
C3 C 0.6753(3) 0.04779(14) 1.5443(2) 0.0265(6) Uani 1 1 d . . . . .
H3 H 0.665394 -0.003613 1.538535 0.032 Uiso 1 1 calc R U . . .
C4 C 0.6348(3) 0.08534(15) 1.6418(2) 0.0261(6) Uani 1 1 d . . . . .
H4 H 0.596695 0.059372 1.701240 0.031 Uiso 1 1 calc R U . . .
C5 C 0.6515(3) 0.16099(14) 1.6498(2) 0.0236(6) Uani 1 1 d . . . . .
H5 H 0.625769 0.186389 1.715608 0.028 Uiso 1 1 calc R U . . .
C6 C 0.7065(3) 0.19989(13) 1.5603(2) 0.0198(5) Uani 1 1 d . . . . .
H6 H 0.716169 0.251284 1.566779 0.024 Uiso 1 1 calc R U . . .
C7 C 0.6092(3) 0.30868(14) 1.2939(2) 0.0213(5) Uani 1 1 d . . . . .
H7 H 0.538509 0.269944 1.285765 0.026 Uiso 1 1 calc R U . . .
C8 C 0.5565(3) 0.37979(15) 1.2617(2) 0.0259(6) Uani 1 1 d . . . . .
H8 H 0.452197 0.388081 1.230442 0.031 Uiso 1 1 calc R U . . .
C9 C 0.6583(3) 0.43832(15) 1.2761(3) 0.0297(6) Uani 1 1 d . . . . .
H9 H 0.623207 0.486212 1.254441 0.036 Uiso 1 1 calc R U . . .
C10 C 0.8124(3) 0.42550(14) 1.3226(3) 0.0301(6) Uani 1 1 d . . . . .
H10 H 0.881331 0.465028 1.334319 0.036 Uiso 1 1 calc R U . . .
C11 C 0.8652(3) 0.35401(14) 1.3519(2) 0.0240(6) Uani 1 1 d . . . . .
H11 H 0.969989 0.346248 1.381639 0.029 Uiso 1 1 calc R U . . .
C12 C 0.7654(3) 0.29318(13) 1.3382(2) 0.0162(5) Uani 1 1 d . . . . .
C13 C 1.1082(3) 0.22050(13) 1.4951(2) 0.0197(5) Uani 1 1 d . . . . .
H13 H 1.078607 0.245249 1.559900 0.024 Uiso 1 1 calc R U . . .
C14 C 1.2640(3) 0.20449(14) 1.5023(2) 0.0216(6) Uani 1 1 d . . . . .
H14 H 1.336648 0.218221 1.572463 0.026 Uiso 1 1 calc R U . . .
C15 C 1.3108(3) 0.16911(13) 1.4079(2) 0.0189(5) Uani 1 1 d . . . . .
H15 H 1.414426 0.158704 1.413847 0.023 Uiso 1 1 calc R U . . .
C16 C 1.2010(3) 0.14848(13) 1.3015(2) 0.0161(5) Uani 1 1 d . . . . .
C17 C 1.2223(3) 0.11365(13) 1.1917(2) 0.0191(5) Uani 1 1 d . . . . .
C18 C 1.1000(3) 0.09736(13) 1.0972(2) 0.0204(5) Uani 1 1 d . . . . .
H18 H 1.117628 0.074999 1.025911 0.024 Uiso 1 1 calc R U . . .
C19 C 0.9480(3) 0.11369(12) 1.1055(2) 0.0179(5) Uani 1 1 d . . . . .
C20 C 0.9195(3) 0.14759(13) 1.2092(2) 0.0168(5) Uani 1 1 d . . . . .
C21 C 1.0480(3) 0.16475(12) 1.3029(2) 0.0154(5) Uani 1 1 d . . . . .
N1 N 1.0034(2) 0.20057(10) 1.39691(17) 0.0157(4) Uani 1 1 d . . . . .
O1 O 0.78709(17) 0.16760(9) 1.23574(14) 0.0180(4) Uani 1 1 d . . . . .
Cl1 Cl 1.40895(7) 0.09581(4) 1.17772(6) 0.02856(19) Uani 1 1 d . . . . .
Cl2 Cl 0.79715(7) 0.09109(4) 0.98471(5) 0.02649(19) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 O1 1.544(3) . ?
B1 C1 1.597(4) . ?
B1 C12 1.595(4) . ?
B1 N1 1.623(3) . ?
C1 C2 1.393(3) . ?
C1 C6 1.396(3) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.382(3) . ?
C7 C12 1.399(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.376(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.397(3) . ?
C11 H11 0.9300 . ?
C13 N1 1.319(3) . ?
C13 C14 1.402(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.364(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.407(3) . ?
C15 H15 0.9300 . ?
C16 C21 1.396(3) . ?
C16 C17 1.418(3) . ?
C17 C18 1.368(3) . ?
C17 Cl1 1.732(2) . ?
C18 C19 1.407(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(3) . ?
C19 Cl2 1.726(2) . ?
C20 O1 1.326(3) . ?
C20 C21 1.402(3) . ?
C21 N1 1.356(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 B1 C1 111.30(19) . . ?
O1 B1 C12 108.90(19) . . ?
C1 B1 C12 116.7(2) . . ?
O1 B1 N1 98.38(17) . . ?
C1 B1 N1 108.40(19) . . ?
C12 B1 N1 111.62(19) . . ?
C2 C1 C6 116.7(2) . . ?
C2 C1 B1 122.0(2) . . ?
C6 C1 B1 121.3(2) . . ?
C3 C2 C1 122.0(2) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 121.6(2) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
C8 C7 C12 122.0(2) . . ?
C8 C7 H7 119.0 . . ?
C12 C7 H7 119.0 . . ?
C9 C8 C7 120.1(2) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 119.5(2) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 120.3(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 121.8(2) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C7 C12 C11 116.3(2) . . ?
C7 C12 B1 118.6(2) . . ?
C11 C12 B1 125.1(2) . . ?
N1 C13 C14 120.3(2) . . ?
N1 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 121.1(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 119.5(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C21 C16 C15 115.9(2) . . ?
C21 C16 C17 114.5(2) . . ?
C15 C16 C17 129.6(2) . . ?
C18 C17 C16 121.2(2) . . ?
C18 C17 Cl1 120.76(19) . . ?
C16 C17 Cl1 117.97(18) . . ?
C17 C18 C19 121.5(2) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C20 C19 C18 120.2(2) . . ?
C20 C19 Cl2 119.96(19) . . ?
C18 C19 Cl2 119.81(18) . . ?
O1 C20 C19 130.0(2) . . ?
O1 C20 C21 113.4(2) . . ?
C19 C20 C21 116.6(2) . . ?
N1 C21 C16 123.9(2) . . ?
N1 C21 C20 110.19(19) . . ?
C16 C21 C20 125.9(2) . . ?
C13 N1 C21 119.3(2) . . ?
C13 N1 B1 132.7(2) . . ?
C21 N1 B1 108.00(18) . . ?
C20 O1 B1 109.89(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 B1 C1 C2 27.7(3) . . . . ?
C12 B1 C1 C2 153.5(2) . . . . ?
N1 B1 C1 C2 -79.5(3) . . . . ?
O1 B1 C1 C6 -154.7(2) . . . . ?
C12 B1 C1 C6 -28.9(3) . . . . ?
N1 B1 C1 C6 98.1(2) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
B1 C1 C2 C3 177.7(2) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
B1 C1 C6 C5 -177.5(2) . . . . ?
C12 C7 C8 C9 -1.8(4) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
C8 C9 C10 C11 1.6(4) . . . . ?
C9 C10 C11 C12 -1.3(4) . . . . ?
C8 C7 C12 C11 2.0(4) . . . . ?
C8 C7 C12 B1 -174.5(2) . . . . ?
C10 C11 C12 C7 -0.4(4) . . . . ?
C10 C11 C12 B1 175.7(2) . . . . ?
O1 B1 C12 C7 65.8(3) . . . . ?
C1 B1 C12 C7 -61.2(3) . . . . ?
N1 B1 C12 C7 173.4(2) . . . . ?
O1 B1 C12 C11 -110.3(3) . . . . ?
C1 B1 C12 C11 122.7(3) . . . . ?
N1 B1 C12 C11 -2.7(3) . . . . ?
N1 C13 C14 C15 0.9(4) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C14 C15 C16 C21 -1.7(3) . . . . ?
C14 C15 C16 C17 178.0(2) . . . . ?
C21 C16 C17 C18 -0.7(3) . . . . ?
C15 C16 C17 C18 179.6(2) . . . . ?
C21 C16 C17 Cl1 176.56(17) . . . . ?
C15 C16 C17 Cl1 -3.1(3) . . . . ?
C16 C17 C18 C19 -0.7(4) . . . . ?
Cl1 C17 C18 C19 -177.94(18) . . . . ?
C17 C18 C19 C20 0.9(4) . . . . ?
C17 C18 C19 Cl2 -179.23(18) . . . . ?
C18 C19 C20 O1 -180.0(2) . . . . ?
Cl2 C19 C20 O1 0.2(4) . . . . ?
C18 C19 C20 C21 0.4(3) . . . . ?
Cl2 C19 C20 C21 -179.48(17) . . . . ?
C15 C16 C21 N1 2.4(3) . . . . ?
C17 C16 C21 N1 -177.3(2) . . . . ?
C15 C16 C21 C20 -178.1(2) . . . . ?
C17 C16 C21 C20 2.2(3) . . . . ?
O1 C20 C21 N1 -2.2(3) . . . . ?
C19 C20 C21 N1 177.52(19) . . . . ?
O1 C20 C21 C16 178.3(2) . . . . ?
C19 C20 C21 C16 -2.0(4) . . . . ?
C14 C13 N1 C21 -0.2(3) . . . . ?
C14 C13 N1 B1 178.4(2) . . . . ?
C16 C21 N1 C13 -1.4(3) . . . . ?
C20 C21 N1 C13 179.0(2) . . . . ?
C16 C21 N1 B1 179.6(2) . . . . ?
C20 C21 N1 B1 0.1(2) . . . . ?
O1 B1 N1 C13 -177.1(2) . . . . ?
C1 B1 N1 C13 -61.2(3) . . . . ?
C12 B1 N1 C13 68.7(3) . . . . ?
O1 B1 N1 C21 1.6(2) . . . . ?
C1 B1 N1 C21 117.5(2) . . . . ?
C12 B1 N1 C21 -112.6(2) . . . . ?
C19 C20 O1 B1 -176.3(2) . . . . ?
C21 C20 O1 B1 3.4(3) . . . . ?
C1 B1 O1 C20 -116.5(2) . . . . ?
C12 B1 O1 C20 113.5(2) . . . . ?
N1 B1 O1 C20 -2.9(2) . . . . ?

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.056

