# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

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

data_gyq_2
_database_code_depnum_ccdc_archive 'CCDC 1484737'
loop_
_audit_author_name
_audit_author_address
'Jing-Cao Dai'
;Huaqiao University
China
;
_audit_update_record             
;
2019-05-13 deposited with the CCDC.	2020-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H30 B F2 N3 O4'
_chemical_formula_weight         593.42

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0378(7)
_cell_length_b                   13.0143(11)
_cell_length_c                   14.5111(11)
_cell_angle_alpha                114.894(8)
_cell_angle_beta                 96.065(6)
_cell_angle_gamma                100.583(7)
_cell_volume                     1489.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2220
_cell_measurement_theta_min      3.1550
_cell_measurement_theta_max      21.5610

_exptl_crystal_description       block
_exptl_crystal_colour            'dark orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             620
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84473
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ??Empirical??
_exptl_special_details           
; 
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.  
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_reflns_number            9721
_diffrn_reflns_av_unetI/netI     0.0969
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.835
_diffrn_reflns_theta_max         25.005
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.950
_reflns_number_total             5121
_reflns_number_gt                2432
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) 
(compiled Aug  2 2013,16:46:58) 
;
_computing_cell_refinement       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) 
(compiled Aug  2 2013,16:46:58) 
;
_computing_data_reduction        
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) 
(compiled Aug  2 2013,16:46:58) 
;
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0872P)²+0.1364P] 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         5121
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1592
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.2124
_refine_ls_wR_factor_gt          0.1625
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
B B 0.3763(5) 0.5088(4) 0.1212(4) 0.0459(12) Uani 1 1 d . . . . .
F1 F 0.4832(3) 0.4446(2) 0.0919(2) 0.0680(8) Uani 1 1 d . . . . .
F2 F 0.2927(3) 0.4713(2) 0.17967(19) 0.0676(8) Uani 1 1 d . . . . .
N1 N 0.2899(5) 0.9433(3) -0.0565(4) 0.0687(11) Uani 1 1 d . . . . .
N2 N 0.4570(3) 0.6397(3) 0.1831(3) 0.0462(8) Uani 1 1 d . . . . .
N3 N 0.2681(3) 0.4936(3) 0.0244(2) 0.0446(8) Uani 1 1 d . . . . .
O1 O 0.7886(5) 0.9899(3) 0.4193(3) 0.1152(15) Uani 1 1 d . . . . .
O2 O 0.7060(4) 0.8634(3) 0.4784(2) 0.0869(12) Uani 1 1 d . . . . .
O3 O -0.0767(4) 0.2272(3) -0.2268(3) 0.0968(13) Uani 1 1 d . . . . .
O4 O -0.0430(3) 0.3535(2) -0.2925(2) 0.0686(9) Uani 1 1 d . . . . .
C1 C 0.1385(4) 0.5346(3) -0.0956(3) 0.0450(10) Uani 1 1 d . . . . .
C2 C 0.0974(5) 0.4144(3) -0.1264(3) 0.0494(10) Uani 1 1 d . . . . .
C3 C 0.1794(4) 0.3919(3) -0.0508(3) 0.0463(10) Uani 1 1 d . . . . .
C4 C 0.2491(4) 0.5834(3) -0.0006(3) 0.0412(9) Uani 1 1 d . . . . .
C5 C 0.5567(5) 0.6891(4) 0.2748(3) 0.0526(11) Uani 1 1 d . . . . .
C6 C 0.6082(5) 0.8109(3) 0.3054(3) 0.0550(11) Uani 1 1 d . . . . .
C7 C 0.5385(5) 0.8352(3) 0.2298(3) 0.0501(11) Uani 1 1 d . . . . .
C8 C 0.3369(4) 0.6976(3) 0.0618(3) 0.0430(10) Uani 1 1 d . . . . .
C9 C 0.4406(4) 0.7269(3) 0.1535(3) 0.0462(10) Uani 1 1 d . . . . .
C10 C 0.7111(6) 0.8978(4) 0.4058(4) 0.0685(14) Uani 1 1 d . . . . .
C11 C -0.0142(5) 0.3215(4) -0.2185(3) 0.0577(12) Uani 1 1 d . . . . .
C12 C 0.5652(5) 0.9529(4) 0.2315(4) 0.0709(14) Uani 1 1 d . . . . .
H12A H 0.5036 0.9468 0.1705 0.106 Uiso 1 1 calc R U . . .
H12B H 0.5373 1.0067 0.2921 0.106 Uiso 1 1 calc R U . . .
H12C H 0.6719 0.9807 0.2330 0.106 Uiso 1 1 calc R U . . .
C13 C 0.6078(5) 0.6185(4) 0.3246(4) 0.0693(14) Uani 1 1 d . . . . .
H13A H 0.6785 0.6697 0.3892 0.104 Uiso 1 1 calc R U . . .
H13B H 0.5201 0.5762 0.3373 0.104 Uiso 1 1 calc R U . . .
H13C H 0.6576 0.5642 0.2794 0.104 Uiso 1 1 calc R U . . .
C14 C 0.0788(5) 0.5966(4) -0.1511(3) 0.0585(12) Uani 1 1 d . . . . .
H14A H 0.1264 0.6790 -0.1130 0.088 Uiso 1 1 calc R U . . .
H14B H 0.1021 0.5674 -0.2192 0.088 Uiso 1 1 calc R U . . .
H14C H -0.0305 0.5834 -0.1569 0.088 Uiso 1 1 calc R U . . .
C15 C 0.1797(5) 0.2768(3) -0.0520(4) 0.0633(12) Uani 1 1 d . . . . .
H15A H 0.1084 0.2154 -0.1122 0.095 Uiso 1 1 calc R U . . .
H15B H 0.2811 0.2645 -0.0541 0.095 Uiso 1 1 calc R U . . .
H15C H 0.1499 0.2765 0.0094 0.095 Uiso 1 1 calc R U . . .
C16 C 0.2218(5) 0.9407(4) 0.0197(4) 0.0647(13) Uani 1 1 d . . . . .
H16A H 0.1599 0.9919 0.0448 0.078 Uiso 1 1 calc R U . . .
C17 C 0.2377(5) 0.8666(4) 0.0640(3) 0.0561(11) Uani 1 1 d . . . . .
H17A H 0.1890 0.8692 0.1180 0.067 Uiso 1 1 calc R U . . .
C18 C 0.3267(4) 0.7892(3) 0.0266(3) 0.0453(10) Uani 1 1 d . . . . .
C19 C 0.4005(4) 0.7932(3) -0.0505(3) 0.0508(11) Uani 1 1 d . . . . .
H19A H 0.4640 0.7438 -0.0767 0.061 Uiso 1 1 calc R U . . .
C20 C 0.3789(5) 0.8719(4) -0.0884(4) 0.0633(13) Uani 1 1 d . . . . .
H20A H 0.4308 0.8742 -0.1398 0.076 Uiso 1 1 calc R U . . .
C21 C 0.7819(6) 0.8827(4) 0.6477(4) 0.0692(14) Uani 1 1 d . . . . .
C22 C 0.9131(6) 0.8991(5) 0.7158(4) 0.0853(16) Uani 1 1 d . . . . .
H22A H 1.0044 0.9502 0.7219 0.102 Uiso 1 1 calc R U . . .
C23 C 0.9071(9) 0.8384(7) 0.7753(5) 0.108(2) Uani 1 1 d . . . . .
H23A H 0.9951 0.8489 0.8211 0.129 Uiso 1 1 calc R U . . .
C24 C 0.7767(12) 0.7654(7) 0.7673(5) 0.110(2) Uani 1 1 d . . . . .
H24A H 0.7755 0.7246 0.8067 0.132 Uiso 1 1 calc R U . . .
C25 C 0.6470(8) 0.7495(5) 0.7034(5) 0.0951(18) Uani 1 1 d . . . . .
H25A H 0.5561 0.7001 0.7004 0.114 Uiso 1 1 calc R U . . .
C26 C 0.6489(6) 0.8071(4) 0.6417(4) 0.0796(15) Uani 1 1 d . . . . .
H26A H 0.5596 0.7944 0.5960 0.096 Uiso 1 1 calc R U . . .
C27 C 0.7903(7) 0.9448(5) 0.5816(4) 0.0965(19) Uani 1 1 d . . . . .
H27A H 0.7460 1.0113 0.6096 0.116 Uiso 1 1 calc R U . . .
H27B H 0.8967 0.9731 0.5802 0.116 Uiso 1 1 calc R U . . .
C28 C -0.1812(5) 0.3273(4) -0.4534(4) 0.0638(13) Uani 1 1 d . . . . .
C29 C -0.2299(6) 0.4276(5) -0.4259(4) 0.0836(16) Uani 1 1 d . . . . .
H29A H -0.2549 0.4628 -0.3611 0.100 Uiso 1 1 calc R U . . .
C30 C -0.2427(7) 0.4772(5) -0.4920(5) 0.0959(19) Uani 1 1 d . . . . .
H30A H -0.2755 0.5458 -0.4714 0.115 Uiso 1 1 calc R U . . .
C31 C -0.2082(7) 0.4278(6) -0.5860(5) 0.0974(19) Uani 1 1 d . . . . .
H31A H -0.2172 0.4619 -0.6305 0.117 Uiso 1 1 calc R U . . .
C32 C -0.1602(7) 0.3280(6) -0.6162(4) 0.103(2) Uani 1 1 d . . . . .
H32A H -0.1362 0.2934 -0.6813 0.123 Uiso 1 1 calc R U . . .
C33 C -0.1469(6) 0.2780(5) -0.5497(4) 0.0808(15) Uani 1 1 d . . . . .
H33A H -0.1141 0.2094 -0.5708 0.097 Uiso 1 1 calc R U . . .
C34 C -0.1648(6) 0.2721(4) -0.3826(4) 0.0797(15) Uani 1 1 d . . . . .
H34A H -0.2608 0.2571 -0.3607 0.096 Uiso 1 1 calc R U . . .
H34B H -0.1380 0.1983 -0.4179 0.096 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
B F2 1.371(5) . ?
B F1 1.376(5) . ?
B N2 1.535(5) . ?
B N3 1.540(5) . ?
N1 C20 1.310(6) . ?
N1 C16 1.330(6) . ?
N2 C5 1.344(5) . ?
N2 C9 1.398(4) . ?
N3 C3 1.339(5) . ?
N3 C4 1.395(4) . ?
O1 C10 1.196(5) . ?
O2 C10 1.309(5) . ?
O2 C27 1.440(6) . ?
O3 C11 1.203(5) . ?
O4 C11 1.323(5) . ?
O4 C34 1.464(5) . ?
C1 C2 1.395(5) . ?
C1 C4 1.429(5) . ?
C1 C14 1.485(5) . ?
C2 C3 1.420(5) . ?
C2 C11 1.475(6) . ?
C3 C15 1.491(5) . ?
C4 C8 1.393(5) . ?
C5 C6 1.420(5) . ?
C5 C13 1.491(5) . ?
C6 C7 1.386(5) . ?
C6 C10 1.485(6) . ?
C7 C9 1.421(5) . ?
C7 C12 1.494(5) . ?
C8 C9 1.405(5) . ?
C8 C18 1.495(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.384(6) . ?
C16 H16A 0.9300 . ?
C17 C18 1.374(5) . ?
C17 H17A 0.9300 . ?
C18 C19 1.376(5) . ?
C19 C20 1.383(5) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
C21 C26 1.376(7) . ?
C21 C22 1.382(7) . ?
C21 C27 1.491(6) . ?
C22 C23 1.394(8) . ?
C22 H22A 0.9300 . ?
C23 C24 1.331(9) . ?
C23 H23A 0.9300 . ?
C24 C25 1.340(9) . ?
C24 H24A 0.9300 . ?
C25 C26 1.388(7) . ?
C25 H25A 0.9300 . ?
C26 H26A 0.9300 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.366(7) . ?
C28 C33 1.368(7) . ?
C28 C34 1.490(6) . ?
C29 C30 1.369(7) . ?
C29 H29A 0.9300 . ?
C30 C31 1.341(7) . ?
C30 H30A 0.9300 . ?
C31 C32 1.355(7) . ?
C31 H31A 0.9300 . ?
C32 C33 1.378(6) . ?
C32 H32A 0.9300 . ?
C33 H33A 0.9300 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?

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
F2 B F1 109.2(4) . . ?
F2 B N2 110.4(4) . . ?
F1 B N2 110.2(3) . . ?
F2 B N3 109.7(3) . . ?
F1 B N3 110.1(4) . . ?
N2 B N3 107.2(3) . . ?
C20 N1 C16 116.4(4) . . ?
C5 N2 C9 108.7(3) . . ?
C5 N2 B 125.4(3) . . ?
C9 N2 B 125.9(3) . . ?
C3 N3 C4 108.7(3) . . ?
C3 N3 B 125.8(3) . . ?
C4 N3 B 125.5(3) . . ?
C10 O2 C27 117.7(4) . . ?
C11 O4 C34 116.8(3) . . ?
C2 C1 C4 105.2(3) . . ?
C2 C1 C14 126.7(4) . . ?
C4 C1 C14 128.1(3) . . ?
C1 C2 C3 108.6(4) . . ?
C1 C2 C11 128.6(4) . . ?
C3 C2 C11 122.8(4) . . ?
N3 C3 C2 108.8(3) . . ?
N3 C3 C15 122.7(4) . . ?
C2 C3 C15 128.4(4) . . ?
C8 C4 N3 120.2(3) . . ?
C8 C4 C1 131.0(4) . . ?
N3 C4 C1 108.7(3) . . ?
N2 C5 C6 108.2(3) . . ?
N2 C5 C13 122.2(4) . . ?
C6 C5 C13 129.3(4) . . ?
C7 C6 C5 108.8(4) . . ?
C7 C6 C10 126.2(4) . . ?
C5 C6 C10 124.9(4) . . ?
C6 C7 C9 105.7(3) . . ?
C6 C7 C12 125.5(4) . . ?
C9 C7 C12 128.8(4) . . ?
C4 C8 C9 121.6(3) . . ?
C4 C8 C18 118.8(3) . . ?
C9 C8 C18 119.5(3) . . ?
N2 C9 C8 119.5(3) . . ?
N2 C9 C7 108.5(3) . . ?
C8 C9 C7 132.0(4) . . ?
O1 C10 O2 123.6(4) . . ?
O1 C10 C6 123.8(4) . . ?
O2 C10 C6 112.6(4) . . ?
O3 C11 O4 122.3(4) . . ?
O3 C11 C2 125.0(4) . . ?
O4 C11 C2 112.6(4) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C14 H14A 109.5 . . ?
C1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C15 H15A 109.5 . . ?
C3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C17 124.0(4) . . ?
N1 C16 H16A 118.0 . . ?
C17 C16 H16A 118.0 . . ?
C18 C17 C16 118.7(4) . . ?
C18 C17 H17A 120.6 . . ?
C16 C17 H17A 120.6 . . ?
C19 C18 C17 117.6(4) . . ?
C19 C18 C8 119.9(4) . . ?
C17 C18 C8 122.3(4) . . ?
C18 C19 C20 119.1(4) . . ?
C18 C19 H19A 120.4 . . ?
C20 C19 H19A 120.4 . . ?
N1 C20 C19 124.1(4) . . ?
N1 C20 H20A 118.0 . . ?
C19 C20 H20A 118.0 . . ?
C26 C21 C22 118.5(5) . . ?
C26 C21 C27 122.4(5) . . ?
C22 C21 C27 119.1(5) . . ?
C21 C22 C23 119.3(6) . . ?
C21 C22 H22A 120.4 . . ?
C23 C22 H22A 120.4 . . ?
C24 C23 C22 120.7(6) . . ?
C24 C23 H23A 119.6 . . ?
C22 C23 H23A 119.6 . . ?
C23 C24 C25 121.3(7) . . ?
C23 C24 H24A 119.4 . . ?
C25 C24 H24A 119.4 . . ?
C24 C25 C26 119.7(6) . . ?
C24 C25 H25A 120.1 . . ?
C26 C25 H25A 120.1 . . ?
C21 C26 C25 120.5(5) . . ?
C21 C26 H26A 119.8 . . ?
C25 C26 H26A 119.8 . . ?
O2 C27 C21 108.1(4) . . ?
O2 C27 H27A 110.1 . . ?
C21 C27 H27A 110.1 . . ?
O2 C27 H27B 110.1 . . ?
C21 C27 H27B 110.1 . . ?
H27A C27 H27B 108.4 . . ?
C29 C28 C33 117.4(5) . . ?
C29 C28 C34 122.3(5) . . ?
C33 C28 C34 120.3(5) . . ?
C28 C29 C30 121.3(5) . . ?
C28 C29 H29A 119.4 . . ?
C30 C29 H29A 119.4 . . ?
C31 C30 C29 120.5(5) . . ?
C31 C30 H30A 119.7 . . ?
C29 C30 H30A 119.7 . . ?
C30 C31 C32 119.9(5) . . ?
C30 C31 H31A 120.1 . . ?
C32 C31 H31A 120.1 . . ?
C31 C32 C33 119.7(5) . . ?
C31 C32 H32A 120.2 . . ?
C33 C32 H32A 120.2 . . ?
C28 C33 C32 121.3(5) . . ?
C28 C33 H33A 119.4 . . ?
C32 C33 H33A 119.4 . . ?
O4 C34 C28 107.6(4) . . ?
O4 C34 H34A 110.2 . . ?
C28 C34 H34A 110.2 . . ?
O4 C34 H34B 110.2 . . ?
C28 C34 H34B 110.2 . . ?
H34A C34 H34B 108.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F2 B N2 C5 58.0(5) . . . . ?
F1 B N2 C5 -62.7(5) . . . . ?
N3 B N2 C5 177.5(4) . . . . ?
F2 B N2 C9 -122.7(4) . . . . ?
F1 B N2 C9 116.6(4) . . . . ?
N3 B N2 C9 -3.2(5) . . . . ?
F2 B N3 C3 -61.6(5) . . . . ?
F1 B N3 C3 58.6(5) . . . . ?
N2 B N3 C3 178.5(3) . . . . ?
F2 B N3 C4 120.0(4) . . . . ?
F1 B N3 C4 -119.8(4) . . . . ?
N2 B N3 C4 0.1(5) . . . . ?
C4 C1 C2 C3 0.9(4) . . . . ?
C14 C1 C2 C3 -179.1(4) . . . . ?
C4 C1 C2 C11 179.2(4) . . . . ?
C14 C1 C2 C11 -0.9(7) . . . . ?
C4 N3 C3 C2 -1.1(4) . . . . ?
B N3 C3 C2 -179.7(3) . . . . ?
C4 N3 C3 C15 175.9(4) . . . . ?
B N3 C3 C15 -2.7(6) . . . . ?
C1 C2 C3 N3 0.1(4) . . . . ?
C11 C2 C3 N3 -178.3(4) . . . . ?
C1 C2 C3 C15 -176.7(4) . . . . ?
C11 C2 C3 C15 4.9(7) . . . . ?
C3 N3 C4 C8 -175.6(3) . . . . ?
B N3 C4 C8 3.0(5) . . . . ?
C3 N3 C4 C1 1.7(4) . . . . ?
B N3 C4 C1 -179.7(3) . . . . ?
C2 C1 C4 C8 175.4(4) . . . . ?
C14 C1 C4 C8 -4.6(7) . . . . ?
C2 C1 C4 N3 -1.6(4) . . . . ?
C14 C1 C4 N3 178.5(4) . . . . ?
C9 N2 C5 C6 -0.7(5) . . . . ?
B N2 C5 C6 178.7(4) . . . . ?
C9 N2 C5 C13 -175.7(4) . . . . ?
B N2 C5 C13 3.7(6) . . . . ?
N2 C5 C6 C7 -0.5(5) . . . . ?
C13 C5 C6 C7 174.1(4) . . . . ?
N2 C5 C6 C10 175.6(4) . . . . ?
C13 C5 C6 C10 -9.8(8) . . . . ?
C5 C6 C7 C9 1.4(5) . . . . ?
C10 C6 C7 C9 -174.6(5) . . . . ?
C5 C6 C7 C12 -178.4(4) . . . . ?
C10 C6 C7 C12 5.6(7) . . . . ?
N3 C4 C8 C9 -3.2(6) . . . . ?
C1 C4 C8 C9 -179.9(4) . . . . ?
N3 C4 C8 C18 173.2(3) . . . . ?
C1 C4 C8 C18 -3.5(6) . . . . ?
C5 N2 C9 C8 -177.4(4) . . . . ?
B N2 C9 C8 3.3(6) . . . . ?
C5 N2 C9 C7 1.5(5) . . . . ?
B N2 C9 C7 -177.8(4) . . . . ?
C4 C8 C9 N2 0.2(6) . . . . ?
C18 C8 C9 N2 -176.2(3) . . . . ?
C4 C8 C9 C7 -178.4(4) . . . . ?
C18 C8 C9 C7 5.3(7) . . . . ?
C6 C7 C9 N2 -1.8(5) . . . . ?
C12 C7 C9 N2 178.0(4) . . . . ?
C6 C7 C9 C8 176.9(4) . . . . ?
C12 C7 C9 C8 -3.3(8) . . . . ?
C27 O2 C10 O1 4.4(8) . . . . ?
C27 O2 C10 C6 -174.5(5) . . . . ?
C7 C6 C10 O1 -27.3(8) . . . . ?
C5 C6 C10 O1 157.3(5) . . . . ?
C7 C6 C10 O2 151.6(4) . . . . ?
C5 C6 C10 O2 -23.7(7) . . . . ?
C34 O4 C11 O3 4.9(7) . . . . ?
C34 O4 C11 C2 -173.6(4) . . . . ?
C1 C2 C11 O3 -157.9(5) . . . . ?
C3 C2 C11 O3 20.1(7) . . . . ?
C1 C2 C11 O4 20.5(7) . . . . ?
C3 C2 C11 O4 -161.4(4) . . . . ?
C20 N1 C16 C17 -1.4(7) . . . . ?
N1 C16 C17 C18 -1.1(7) . . . . ?
C16 C17 C18 C19 2.6(6) . . . . ?
C16 C17 C18 C8 -173.4(4) . . . . ?
C4 C8 C18 C19 -76.3(5) . . . . ?
C9 C8 C18 C19 100.2(5) . . . . ?
C4 C8 C18 C17 99.6(5) . . . . ?
C9 C8 C18 C17 -83.9(5) . . . . ?
C17 C18 C19 C20 -1.7(6) . . . . ?
C8 C18 C19 C20 174.4(4) . . . . ?
C16 N1 C20 C19 2.4(7) . . . . ?
C18 C19 C20 N1 -0.9(7) . . . . ?
C26 C21 C22 C23 0.5(8) . . . . ?
C27 C21 C22 C23 -177.9(5) . . . . ?
C21 C22 C23 C24 -0.2(9) . . . . ?
C22 C23 C24 C25 -1.1(11) . . . . ?
C23 C24 C25 C26 2.1(10) . . . . ?
C22 C21 C26 C25 0.4(8) . . . . ?
C27 C21 C26 C25 178.8(5) . . . . ?
C24 C25 C26 C21 -1.8(9) . . . . ?
C10 O2 C27 C21 -173.9(5) . . . . ?
C26 C21 C27 O2 -41.5(8) . . . . ?
C22 C21 C27 O2 136.9(5) . . . . ?
C33 C28 C29 C30 -0.5(8) . . . . ?
C34 C28 C29 C30 179.4(5) . . . . ?
C28 C29 C30 C31 0.4(9) . . . . ?
C29 C30 C31 C32 -0.1(10) . . . . ?
C30 C31 C32 C33 0.0(10) . . . . ?
C29 C28 C33 C32 0.4(8) . . . . ?
C34 C28 C33 C32 -179.5(5) . . . . ?
C31 C32 C33 C28 -0.1(9) . . . . ?
C11 O4 C34 C28 177.9(4) . . . . ?
C29 C28 C34 O4 -65.0(6) . . . . ?
C33 C28 C34 O4 114.9(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C13 H13A O2 0.96 2.25 2.912(6) 125.6 .
C13 H13B F2 0.96 2.58 3.089(5) 113.2 .
C13 H13C F1 0.96 2.63 3.101(5) 110.4 .
C15 H15A O3 0.96 2.30 3.008(6) 129.6 .
C15 H15B F1 0.96 2.60 3.067(5) 110.3 .
C17 H17A O3 0.93 2.58 3.419(6) 151.0 2_565
C19 H19A F1 0.93 2.51 3.289(5) 141.8 2_665
C34 H34B O1 0.97 2.64 3.495(7) 146.7 1_444

_refine_diff_density_max         0.290
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.049

_shelxl_version_number           2014-3

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

data_exp_3433new
_database_code_depnum_ccdc_archive 'CCDC 1915589'
loop_
_audit_author_name
_audit_author_address
'Jing-Cao Dai'
;Huaqiao University
China
;
_audit_update_record             
;
2019-05-13 deposited with the CCDC.	2020-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H26 B F2 N3 O6'
_chemical_formula_weight         477.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.9602(2)
_cell_length_b                   22.9534(4)
_cell_length_c                   9.64470(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.1620(10)
_cell_angle_gamma                90
_cell_volume                     2201.62(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    114(2)
_cell_measurement_reflns_used    3507
_cell_measurement_theta_min      4.4290
_cell_measurement_theta_max      71.3130

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   'not measured'
_exptl_transmission_factor_max   'not measured'
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.977
_shelx_estimated_absorpt_T_min   0.909
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.88731
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_diffrn_ambient_temperature      114(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_reflns_number            7791
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.887
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             3869
_reflns_number_gt                3200
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELTL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELTL-2014 (Sheldrick, 2014)'

_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)+(0.1567P)²+5.1948P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3869
_refine_ls_number_parameters     295
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0859
_refine_ls_wR_factor_ref         0.2657
_refine_ls_wR_factor_gt          0.2504
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.049
_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
B B 0.1818(4) 0.55434(18) 0.4003(4) 0.0186(8) Uani 1 1 d . . . . .
F1 F 0.1069(2) 0.59369(9) 0.4742(2) 0.0233(5) Uani 1 1 d . . . . .
F2 F 0.2686(2) 0.58403(9) 0.3185(2) 0.0242(5) Uani 1 1 d . . . . .
N1 N 0.2158(4) 0.23896(15) 0.3393(4) 0.0381(9) Uani 1 1 d . . . . .
N2 N 0.2626(3) 0.51357(12) 0.5030(3) 0.0182(7) Uani 1 1 d . . . . .
N3 N 0.0859(3) 0.51464(12) 0.3102(3) 0.0184(7) Uani 1 1 d . . . . .
O1 O 0.5161(3) 0.43921(12) 0.8696(2) 0.0247(6) Uani 1 1 d D . . . .
O2 O 0.5803(3) 0.52879(11) 0.8094(3) 0.0248(6) Uani 1 1 d . . . . .
O3 O -0.2693(3) 0.44195(12) 0.0409(3) 0.0318(7) Uani 1 1 d . . . . .
O4 O -0.2212(3) 0.53490(12) 0.0009(3) 0.0277(6) Uani 1 1 d D . . . .
C1 C -0.0164(4) 0.43372(16) 0.2166(3) 0.0201(7) Uani 1 1 d . . . . .
C2 C -0.0788(4) 0.48337(15) 0.1609(3) 0.0199(8) Uani 1 1 d . . . . .
C3 C -0.0120(3) 0.53296(16) 0.2184(3) 0.0192(7) Uani 1 1 d . . . . .
C4 C 0.0880(3) 0.45364(15) 0.3102(3) 0.0179(7) Uani 1 1 d . . . . .
C5 C 0.3514(3) 0.53125(16) 0.6050(3) 0.0193(7) Uani 1 1 d . . . . .
C6 C 0.4088(3) 0.48172(15) 0.6716(3) 0.0195(8) Uani 1 1 d . . . . .
C7 C 0.3563(3) 0.43210(15) 0.6050(3) 0.0182(7) Uani 1 1 d . . . . .
C8 C 0.1798(3) 0.42319(15) 0.3997(3) 0.0179(7) Uani 1 1 d . . . . .
C9 C 0.2634(3) 0.45234(15) 0.4983(3) 0.0176(7) Uani 1 1 d . . . . .
C10 C 0.5094(4) 0.48484(15) 0.7888(3) 0.0193(7) Uani 1 1 d . . . . .
C11 C -0.1974(4) 0.48504(15) 0.0623(3) 0.0201(8) Uani 1 1 d . . . . .
C12 C 0.3945(4) 0.37035(16) 0.6397(4) 0.0228(8) Uani 1 1 d . . . . .
H12A H 0.3431 0.3438 0.5775 0.034 Uiso 1 1 calc R U . . .
H12B H 0.4908 0.3649 0.6283 0.034 Uiso 1 1 calc R U . . .
H12C H 0.3746 0.3621 0.7361 0.034 Uiso 1 1 calc R U . . .
C13 C 0.3767(4) 0.59366(15) 0.6370(4) 0.0225(8) Uani 1 1 d . . . . .
H13A H 0.4444 0.5969 0.7142 0.034 Uiso 1 1 calc R U . . .
H13B H 0.4094 0.6132 0.5550 0.034 Uiso 1 1 calc R U . . .
H13C H 0.2929 0.6121 0.6628 0.034 Uiso 1 1 calc R U . . .
C14 C -0.0535(4) 0.37189(17) 0.1845(4) 0.0267(8) Uani 1 1 d . . . . .
H14A H 0.0072 0.3458 0.2384 0.040 Uiso 1 1 calc R U . . .
H14B H -0.1463 0.3648 0.2090 0.040 Uiso 1 1 calc R U . . .
H14C H -0.0456 0.3645 0.0852 0.040 Uiso 1 1 calc R U . . .
C15 C -0.0356(4) 0.59585(16) 0.1892(4) 0.0247(8) Uani 1 1 d . . . . .
H15A H -0.1107 0.6001 0.1199 0.037 Uiso 1 1 calc R U . . .
H15B H -0.0572 0.6158 0.2750 0.037 Uiso 1 1 calc R U . . .
H15C H 0.0457 0.6131 0.1534 0.037 Uiso 1 1 calc R U . . .
C16 C 0.2817(4) 0.27732(18) 0.2659(5) 0.0335(9) Uani 1 1 d . . . . .
H16A H 0.3383 0.2629 0.1976 0.040 Uiso 1 1 calc R U . . .
C17 C 0.2731(4) 0.33727(17) 0.2829(4) 0.0256(8) Uani 1 1 d . . . . .
H17A H 0.3219 0.3629 0.2271 0.031 Uiso 1 1 calc R U . . .
C18 C 0.1914(3) 0.35893(16) 0.3835(3) 0.0204(7) Uani 1 1 d . . . . .
C19 C 0.1224(4) 0.31920(16) 0.4620(4) 0.0253(8) Uani 1 1 d . . . . .
H19A H 0.0657 0.3321 0.5319 0.030 Uiso 1 1 calc R U . . .
C20 C 0.1386(4) 0.26032(17) 0.4356(4) 0.0326(9) Uani 1 1 d . . . . .
H20A H 0.0915 0.2334 0.4899 0.039 Uiso 1 1 calc R U . . .
O01 O -0.342(2) 0.2615(8) 0.046(2) 0.306(9) Uiso 1 1 d . . . . .
O02 O -0.3293(19) 0.2408(7) 0.289(2) 0.279(7) Uiso 1 1 d . . . . .
C01 C -0.2506(15) 0.2374(7) 0.1568(16) 0.149(5) Uiso 1 1 d . . . . .
C02 C -0.2486(17) 0.2427(7) 0.4191(18) 0.167(5) Uiso 1 1 d . . . . .
H01 H 0.591(3) 0.442(3) 0.918(5) 0.054(16) Uiso 1 1 d D . . . .
H04 H -0.287(4) 0.532(3) -0.059(5) 0.058(17) Uiso 1 1 d 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
B F2 1.382(4) . ?
B F1 1.393(4) . ?
B N3 1.551(5) . ?
B N2 1.555(5) . ?
N1 C16 1.326(6) . ?
N1 C20 1.332(6) . ?
N2 C5 1.348(4) . ?
N2 C9 1.406(5) . ?
N3 C3 1.348(4) . ?
N3 C4 1.400(5) . ?
O1 C10 1.305(4) . ?
O1 H01 0.86(2) . ?
O2 C10 1.241(4) . ?
O3 C11 1.231(5) . ?
O4 C11 1.304(4) . ?
O4 H04 0.85(2) . ?
C1 C2 1.391(5) . ?
C1 C4 1.415(5) . ?
C1 C14 1.494(5) . ?
C2 C3 1.416(5) . ?
C2 C11 1.476(5) . ?
C3 C15 1.487(5) . ?
C4 C8 1.408(5) . ?
C5 C6 1.411(5) . ?
C5 C13 1.484(5) . ?
C6 C7 1.395(5) . ?
C6 C10 1.471(5) . ?
C7 C9 1.424(5) . ?
C7 C12 1.500(5) . ?
C8 C9 1.399(5) . ?
C8 C18 1.488(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.389(6) . ?
C16 H16A 0.9500 . ?
C17 C18 1.392(5) . ?
C17 H17A 0.9500 . ?
C18 C19 1.391(5) . ?
C19 C20 1.386(6) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9500 . ?
O01 C01 1.47(2) . ?
O01 C02 1.58(2) 4_565 ?
O02 C02 1.45(2) . ?
O02 C01 1.536(19) . ?
C02 O01 1.58(2) 4_566 ?

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
F2 B F1 110.0(3) . . ?
F2 B N3 110.8(3) . . ?
F1 B N3 109.7(3) . . ?
F2 B N2 110.0(3) . . ?
F1 B N2 109.7(3) . . ?
N3 B N2 106.5(3) . . ?
C16 N1 C20 116.7(4) . . ?
C5 N2 C9 108.7(3) . . ?
C5 N2 B 125.4(3) . . ?
C9 N2 B 125.7(3) . . ?
C3 N3 C4 108.8(3) . . ?
C3 N3 B 125.8(3) . . ?
C4 N3 B 125.4(3) . . ?
C10 O1 H01 106(4) . . ?
C11 O4 H04 111(4) . . ?
C2 C1 C4 106.2(3) . . ?
C2 C1 C14 126.7(3) . . ?
C4 C1 C14 127.1(3) . . ?
C1 C2 C3 108.5(3) . . ?
C1 C2 C11 126.5(3) . . ?
C3 C2 C11 125.0(3) . . ?
N3 C3 C2 108.3(3) . . ?
N3 C3 C15 121.9(3) . . ?
C2 C3 C15 129.8(3) . . ?
N3 C4 C8 120.3(3) . . ?
N3 C4 C1 108.3(3) . . ?
C8 C4 C1 131.3(3) . . ?
N2 C5 C6 108.8(3) . . ?
N2 C5 C13 122.6(3) . . ?
C6 C5 C13 128.6(3) . . ?
C7 C6 C5 108.4(3) . . ?
C7 C6 C10 128.0(3) . . ?
C5 C6 C10 123.5(3) . . ?
C6 C7 C9 106.2(3) . . ?
C6 C7 C12 125.8(3) . . ?
C9 C7 C12 128.0(3) . . ?
C9 C8 C4 121.4(3) . . ?
C9 C8 C18 119.9(3) . . ?
C4 C8 C18 118.6(3) . . ?
C8 C9 N2 119.8(3) . . ?
C8 C9 C7 132.4(3) . . ?
N2 C9 C7 107.9(3) . . ?
O2 C10 O1 123.2(3) . . ?
O2 C10 C6 121.3(3) . . ?
O1 C10 C6 115.5(3) . . ?
O3 C11 O4 122.6(3) . . ?
O3 C11 C2 121.6(3) . . ?
O4 C11 C2 115.7(3) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C14 H14A 109.5 . . ?
C1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C15 H15A 109.5 . . ?
C3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C17 124.0(4) . . ?
N1 C16 H16A 118.0 . . ?
C17 C16 H16A 118.0 . . ?
C16 C17 C18 118.6(4) . . ?
C16 C17 H17A 120.7 . . ?
C18 C17 H17A 120.7 . . ?
C19 C18 C17 118.1(3) . . ?
C19 C18 C8 123.3(3) . . ?
C17 C18 C8 118.6(3) . . ?
C20 C19 C18 118.3(4) . . ?
C20 C19 H19A 120.9 . . ?
C18 C19 H19A 120.9 . . ?
N1 C20 C19 124.4(4) . . ?
N1 C20 H20A 117.8 . . ?
C19 C20 H20A 117.8 . . ?
C01 O01 C02 100.1(14) . 4_565 ?
C02 O02 C01 115.8(15) . . ?
O01 C01 O02 105.1(14) . . ?
O02 C02 O01 110.4(14) . 4_566 ?

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
F2 B N2 C5 64.0(4) . . . . ?
F1 B N2 C5 -57.2(4) . . . . ?
N3 B N2 C5 -175.9(3) . . . . ?
F2 B N2 C9 -110.7(4) . . . . ?
F1 B N2 C9 128.1(3) . . . . ?
N3 B N2 C9 9.4(4) . . . . ?
F2 B N3 C3 -68.0(4) . . . . ?
F1 B N3 C3 53.7(4) . . . . ?
N2 B N3 C3 172.4(3) . . . . ?
F2 B N3 C4 111.4(4) . . . . ?
F1 B N3 C4 -127.0(3) . . . . ?
N2 B N3 C4 -8.3(4) . . . . ?
C4 C1 C2 C3 0.8(4) . . . . ?
C14 C1 C2 C3 -179.7(3) . . . . ?
C4 C1 C2 C11 -177.2(3) . . . . ?
C14 C1 C2 C11 2.3(6) . . . . ?
C4 N3 C3 C2 2.2(4) . . . . ?
B N3 C3 C2 -178.3(3) . . . . ?
C4 N3 C3 C15 -177.0(3) . . . . ?
B N3 C3 C15 2.4(5) . . . . ?
C1 C2 C3 N3 -1.9(4) . . . . ?
C11 C2 C3 N3 176.2(3) . . . . ?
C1 C2 C3 C15 177.2(3) . . . . ?
C11 C2 C3 C15 -4.7(6) . . . . ?
C3 N3 C4 C8 -178.7(3) . . . . ?
B N3 C4 C8 1.9(5) . . . . ?
C3 N3 C4 C1 -1.7(4) . . . . ?
B N3 C4 C1 178.8(3) . . . . ?
C2 C1 C4 N3 0.5(4) . . . . ?
C14 C1 C4 N3 -179.0(3) . . . . ?
C2 C1 C4 C8 177.0(3) . . . . ?
C14 C1 C4 C8 -2.4(6) . . . . ?
C9 N2 C5 C6 -1.8(4) . . . . ?
B N2 C5 C6 -177.2(3) . . . . ?
C9 N2 C5 C13 179.3(3) . . . . ?
B N2 C5 C13 3.9(5) . . . . ?
N2 C5 C6 C7 2.0(4) . . . . ?
C13 C5 C6 C7 -179.2(3) . . . . ?
N2 C5 C6 C10 -179.6(3) . . . . ?
C13 C5 C6 C10 -0.7(6) . . . . ?
C5 C6 C7 C9 -1.3(4) . . . . ?
C10 C6 C7 C9 -179.7(3) . . . . ?
C5 C6 C7 C12 177.6(3) . . . . ?
C10 C6 C7 C12 -0.8(6) . . . . ?
N3 C4 C8 C9 5.3(5) . . . . ?
C1 C4 C8 C9 -170.9(3) . . . . ?
N3 C4 C8 C18 -172.0(3) . . . . ?
C1 C4 C8 C18 11.9(6) . . . . ?
C4 C8 C9 N2 -4.2(5) . . . . ?
C18 C8 C9 N2 173.0(3) . . . . ?
C4 C8 C9 C7 175.2(3) . . . . ?
C18 C8 C9 C7 -7.6(6) . . . . ?
C5 N2 C9 C8 -179.5(3) . . . . ?
B N2 C9 C8 -4.1(5) . . . . ?
C5 N2 C9 C7 1.0(4) . . . . ?
B N2 C9 C7 176.4(3) . . . . ?
C6 C7 C9 C8 -179.2(4) . . . . ?
C12 C7 C9 C8 1.9(6) . . . . ?
C6 C7 C9 N2 0.2(4) . . . . ?
C12 C7 C9 N2 -178.7(3) . . . . ?
C7 C6 C10 O2 155.5(4) . . . . ?
C5 C6 C10 O2 -22.7(5) . . . . ?
C7 C6 C10 O1 -25.9(5) . . . . ?
C5 C6 C10 O1 155.9(3) . . . . ?
C1 C2 C11 O3 14.9(6) . . . . ?
C3 C2 C11 O3 -162.9(4) . . . . ?
C1 C2 C11 O4 -165.6(3) . . . . ?
C3 C2 C11 O4 16.6(5) . . . . ?
C20 N1 C16 C17 -0.8(6) . . . . ?
N1 C16 C17 C18 0.5(6) . . . . ?
C16 C17 C18 C19 0.0(5) . . . . ?
C16 C17 C18 C8 -178.7(3) . . . . ?
C9 C8 C18 C19 87.1(4) . . . . ?
C4 C8 C18 C19 -95.7(4) . . . . ?
C9 C8 C18 C17 -94.3(4) . . . . ?
C4 C8 C18 C17 83.0(4) . . . . ?
C17 C18 C19 C20 -0.1(5) . . . . ?
C8 C18 C19 C20 178.5(3) . . . . ?
C16 N1 C20 C19 0.7(6) . . . . ?
C18 C19 C20 N1 -0.3(6) . . . . ?
C02 O01 C01 O02 178.4(13) 4_565 . . . ?
C02 O02 C01 O01 -155.7(16) . . . . ?
C01 O02 C02 O01 -173.4(14) . . . 4_566 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C13 H13A O2 0.98 2.23 2.954(4) 129.5 .
C15 H15A O4 0.98 2.15 2.882(4) 130.0 .
C15 H15B F1 0.98 2.50 3.023(4) 112.9 .
C19 H19A F1 0.95 2.42 3.122(4) 130.7 3_566
O1 H01 O3 0.86(2) 1.77(2) 2.629(3) 170(6) 1_656
O4 H04 O2 0.85(2) 1.78(2) 2.633(3) 177(6) 1_454

_refine_diff_density_max         1.556
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.107

_shelxl_version_number           2014-3

