# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

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

data_40719m
_database_code_depnum_ccdc_archive 'CCDC 2086719'
loop_
_audit_author_name
_audit_author_address
'Nobuhiro Yasuda'
;Japan Synchrotron Radiation Research Institute
Japan
;
_audit_update_record             
;
2021-05-29 deposited with the CCDC.	2021-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 B F N2 O2'
_chemical_formula_sum            'C17 H14 B F N2 O2'
_chemical_formula_weight         308.11

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'
F F 0.0727 0.0534 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4

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

_cell_length_a                   11.7384(10)
_cell_length_b                   5.679(5)
_cell_length_c                   12.3352(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.405(18)
_cell_angle_gamma                90.00
_cell_volume                     736.5(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    788
_cell_measurement_theta_min      25.8
_cell_measurement_theta_max      68.2

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5589
_exptl_absorpt_correction_T_max  0.9523
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5258
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         6.99
_diffrn_reflns_theta_max         66.00
_reflns_number_total             2188
_reflns_number_gt                1896
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0900P)²+0.4469P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_number_reflns         2188
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1424
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2470(2) 0.7784(4) 0.24003(18) 0.0220(6) Uani 1 1 d . . .
O2 O 0.10161(19) 0.4402(4) 0.18311(18) 0.0211(5) Uani 1 1 d . . .
N1 N 0.3514(2) 1.1714(5) 0.3669(2) 0.0209(6) Uani 1 1 d . . .
H1 H 0.3632 1.1530 0.3018 0.025 Uiso 1 1 calc R . .
N2 N -0.0858(2) 0.1797(6) 0.1935(2) 0.0227(7) Uani 1 1 d . . .
H2 H -0.0745 0.1532 0.1287 0.027 Uiso 1 1 calc R . .
C1 C 0.4040(3) 1.3444(7) 0.4497(3) 0.0230(7) Uani 1 1 d . . .
H3 H 0.4574 1.4671 0.4463 0.028 Uiso 1 1 calc R . .
C2 C 0.3664(3) 1.3111(7) 0.5406(3) 0.0236(8) Uani 1 1 d . . .
H4 H 0.3904 1.4050 0.6112 0.028 Uiso 1 1 calc R . .
C3 C 0.2866(3) 1.1137(7) 0.5093(3) 0.0235(8) Uani 1 1 d . . .
H5 H 0.2464 1.0494 0.5545 0.028 Uiso 1 1 calc R . .
C4 C 0.2770(3) 1.0287(6) 0.3990(3) 0.0194(7) Uani 1 1 d . . .
C5 C 0.2113(3) 0.8323(6) 0.3243(3) 0.0196(7) Uani 1 1 d . . .
C6 C 0.1180(3) 0.7011(7) 0.3377(3) 0.0197(7) Uani 1 1 d . . .
H6 H 0.0895 0.7468 0.3956 0.024 Uiso 1 1 calc R . .
C7 C 0.0670(3) 0.5050(7) 0.2667(3) 0.0215(7) Uani 1 1 d . . .
C8 C -0.0248(3) 0.3521(6) 0.2780(3) 0.0204(7) Uani 1 1 d . . .
C9 C -0.0672(3) 0.3335(7) 0.3666(3) 0.0261(8) Uani 1 1 d . . .
H7 H -0.0415 0.4292 0.4367 0.031 Uiso 1 1 calc R . .
C10 C -0.1551(3) 0.1474(8) 0.3333(3) 0.0281(9) Uani 1 1 d . . .
H8 H -0.1993 0.0936 0.3770 0.034 Uiso 1 1 calc R . .
C11 C -0.1657(3) 0.0566(7) 0.2247(3) 0.0249(8) Uani 1 1 d . . .
H9 H -0.2193 -0.0694 0.1802 0.030 Uiso 1 1 calc R . .
C12 C 0.2796(3) 0.4450(6) 0.1192(3) 0.0192(7) Uani 1 1 d . . .
C13 C 0.2422(3) 0.2342(7) 0.0517(3) 0.0240(8) Uani 1 1 d . . .
H10 H 0.1554 0.1882 0.0173 0.029 Uiso 1 1 calc R . .
C14 C 0.3299(3) 0.0914(7) 0.0344(3) 0.0288(8) Uani 1 1 d . . .
H11 H 0.3024 -0.0484 -0.0124 0.035 Uiso 1 1 calc R . .
C15 C 0.4583(3) 0.1561(8) 0.0864(3) 0.0297(8) Uani 1 1 d . . .
H12 H 0.5186 0.0593 0.0759 0.036 Uiso 1 1 calc R . .
C16 C 0.4971(3) 0.3607(7) 0.1531(3) 0.0285(8) Uani 1 1 d . . .
H13 H 0.5843 0.4040 0.1884 0.034 Uiso 1 1 calc R . .
C17 C 0.4097(3) 0.5046(7) 0.1692(3) 0.0241(8) Uani 1 1 d . . .
H14 H 0.4383 0.6457 0.2148 0.029 Uiso 1 1 calc R . .
F1 F 0.09125(16) 0.7191(4) 0.04049(15) 0.0255(5) Uani 1 1 d . . .
B1 B 0.1792(3) 0.5996(8) 0.1444(3) 0.0198(8) 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
O1 C5 1.318(4) . ?
O1 B1 1.490(4) . ?
O2 C7 1.317(4) . ?
O2 B1 1.505(4) . ?
N1 C1 1.352(5) . ?
N1 C4 1.372(4) . ?
N1 H1 0.8800 . ?
N2 C11 1.355(4) . ?
N2 C8 1.375(4) . ?
N2 H2 0.8800 . ?
C1 C2 1.389(5) . ?
C1 H3 0.9500 . ?
C2 C3 1.400(5) . ?
C2 H4 0.9500 . ?
C3 C4 1.400(4) . ?
C3 H5 0.9500 . ?
C4 C5 1.433(5) . ?
C5 C6 1.394(5) . ?
C6 C7 1.378(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.438(5) . ?
C8 C9 1.393(4) . ?
C9 C10 1.405(5) . ?
C9 H7 0.9500 . ?
C10 C11 1.388(5) . ?
C10 H8 0.9500 . ?
C11 H9 0.9500 . ?
C12 C17 1.410(4) . ?
C12 C13 1.411(5) . ?
C12 B1 1.607(5) . ?
C13 C14 1.400(5) . ?
C13 H10 0.9500 . ?
C14 C15 1.399(5) . ?
C14 H11 0.9500 . ?
C15 C16 1.378(6) . ?
C15 H12 0.9500 . ?
C16 C17 1.393(5) . ?
C16 H13 0.9500 . ?
C17 H14 0.9500 . ?
F1 B1 1.411(4) . ?

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
C5 O1 B1 122.5(2) . . ?
C7 O2 B1 121.4(3) . . ?
C1 N1 C4 110.3(3) . . ?
C1 N1 H1 124.8 . . ?
C4 N1 H1 124.8 . . ?
C11 N2 C8 110.2(3) . . ?
C11 N2 H2 124.9 . . ?
C8 N2 H2 124.9 . . ?
N1 C1 C2 108.0(3) . . ?
N1 C1 H3 126.0 . . ?
C2 C1 H3 126.0 . . ?
C1 C2 C3 107.5(3) . . ?
C1 C2 H4 126.3 . . ?
C3 C2 H4 126.3 . . ?
C4 C3 C2 107.4(3) . . ?
C4 C3 H5 126.3 . . ?
C2 C3 H5 126.3 . . ?
N1 C4 C3 106.8(3) . . ?
N1 C4 C5 120.3(3) . . ?
C3 C4 C5 132.9(3) . . ?
O1 C5 C6 120.7(3) . . ?
O1 C5 C4 114.7(3) . . ?
C6 C5 C4 124.5(3) . . ?
C7 C6 C5 119.9(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
O2 C7 C6 121.7(3) . . ?
O2 C7 C8 114.3(3) . . ?
C6 C7 C8 123.9(3) . . ?
N2 C8 C9 107.0(3) . . ?
N2 C8 C7 121.1(3) . . ?
C9 C8 C7 131.8(3) . . ?
C8 C9 C10 107.5(3) . . ?
C8 C9 H7 126.3 . . ?
C10 C9 H7 126.3 . . ?
C11 C10 C9 107.5(3) . . ?
C11 C10 H8 126.3 . . ?
C9 C10 H8 126.3 . . ?
N2 C11 C10 107.8(3) . . ?
N2 C11 H9 126.1 . . ?
C10 C11 H9 126.1 . . ?
C17 C12 C13 117.0(3) . . ?
C17 C12 B1 121.9(3) . . ?
C13 C12 B1 120.9(3) . . ?
C14 C13 C12 121.6(3) . . ?
C14 C13 H10 119.2 . . ?
C12 C13 H10 119.2 . . ?
C13 C14 C15 119.5(4) . . ?
C13 C14 H11 120.2 . . ?
C15 C14 H11 120.2 . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 H12 120.1 . . ?
C14 C15 H12 120.1 . . ?
C15 C16 C17 120.7(3) . . ?
C15 C16 H13 119.6 . . ?
C17 C16 H13 119.6 . . ?
C16 C17 C12 121.3(3) . . ?
C16 C17 H14 119.4 . . ?
C12 C17 H14 119.4 . . ?
F1 B1 O1 108.0(3) . . ?
F1 B1 O2 106.0(2) . . ?
O1 B1 O2 110.1(2) . . ?
F1 B1 C12 113.0(2) . . ?
O1 B1 C12 110.2(2) . . ?
O2 B1 C12 109.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 1.7(4) . . . . ?
N1 C1 C2 C3 -1.1(4) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C1 N1 C4 C3 -1.6(4) . . . . ?
C1 N1 C4 C5 180.0(3) . . . . ?
C2 C3 C4 N1 0.9(4) . . . . ?
C2 C3 C4 C5 179.0(3) . . . . ?
B1 O1 C5 C6 8.7(4) . . . . ?
B1 O1 C5 C4 -172.3(3) . . . . ?
N1 C4 C5 O1 12.1(4) . . . . ?
C3 C4 C5 O1 -165.8(3) . . . . ?
N1 C4 C5 C6 -169.0(3) . . . . ?
C3 C4 C5 C6 13.1(6) . . . . ?
O1 C5 C6 C7 3.5(5) . . . . ?
C4 C5 C6 C7 -175.3(3) . . . . ?
B1 O2 C7 C6 -11.7(4) . . . . ?
B1 O2 C7 C8 169.5(3) . . . . ?
C5 C6 C7 O2 -1.9(5) . . . . ?
C5 C6 C7 C8 176.7(3) . . . . ?
C11 N2 C8 C9 0.8(4) . . . . ?
C11 N2 C8 C7 178.9(3) . . . . ?
O2 C7 C8 N2 -10.8(4) . . . . ?
C6 C7 C8 N2 170.4(3) . . . . ?
O2 C7 C8 C9 166.8(4) . . . . ?
C6 C7 C8 C9 -12.0(6) . . . . ?
N2 C8 C9 C10 -0.2(4) . . . . ?
C7 C8 C9 C10 -178.1(4) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C8 N2 C11 C10 -1.1(4) . . . . ?
C9 C10 C11 N2 0.9(4) . . . . ?
C17 C12 C13 C14 -0.5(5) . . . . ?
B1 C12 C13 C14 -176.6(3) . . . . ?
C12 C13 C14 C15 1.0(5) . . . . ?
C13 C14 C15 C16 -0.7(5) . . . . ?
C14 C15 C16 C17 -0.1(5) . . . . ?
C15 C16 C17 C12 0.6(5) . . . . ?
C13 C12 C17 C16 -0.3(5) . . . . ?
B1 C12 C17 C16 175.7(3) . . . . ?
C5 O1 B1 F1 95.6(3) . . . . ?
C5 O1 B1 O2 -19.8(4) . . . . ?
C5 O1 B1 C12 -140.6(3) . . . . ?
C7 O2 B1 F1 -95.4(3) . . . . ?
C7 O2 B1 O1 21.2(4) . . . . ?
C7 O2 B1 C12 142.5(3) . . . . ?
C17 C12 B1 F1 111.6(3) . . . . ?
C13 C12 B1 F1 -72.5(4) . . . . ?
C17 C12 B1 O1 -9.3(4) . . . . ?
C13 C12 B1 O1 166.6(3) . . . . ?
C17 C12 B1 O2 -130.5(3) . . . . ?
C13 C12 B1 O2 45.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        66.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.070
####################################################################### 
# 
# 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_ydkr
_database_code_depnum_ccdc_archive 'CCDC 2086720'
loop_
_audit_author_name
_audit_author_address
'Nobuhiro Yasuda'
;Japan Synchrotron Radiation Research Institute
Japan
;
_audit_update_record             
;
2021-05-29 deposited with the CCDC.	2021-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        aPh-BFPh
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C29 H22 B F N2 O2, C2 H4 Cl2'
_chemical_formula_sum            'C31 H26 B Cl2 F N2 O2'
_chemical_formula_weight         559.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0020 0.0021 '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 -0.0010 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1472 0.2018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F -0.0053 0.0127 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N -0.0031 0.0043 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0042 0.0079 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   5.2329(2)
_cell_length_b                   24.0253(11)
_cell_length_c                   21.2592(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.778(3)
_cell_angle_gamma                90
_cell_volume                     2659.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8453
_cell_measurement_theta_min      4.392
_cell_measurement_theta_max      30.011

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             1160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.386
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.8000
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'synchrotron radiation SPring-8 BL38B1'
_diffrn_measurement_device_type  'CCD MX225HE(Rayonix)'
_diffrn_measurement_method       'w scans'
_diffrn_measurement.details      
' 3.00 degrees, 21.9 sec, detector distance 75.00 mm'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8453
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         4.392
_diffrn_reflns_theta_max         30.011
_diffrn_reflns_theta_full        28.685
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.471
_diffrn_reflns_point_group_measured_fraction_full 0.485
_reflns_number_total             2571
_reflns_number_gt                2544
_reflns_threshold_expression     'I > 2s(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

_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       HKL2000
_computing_cell_refinement       HKL2000
_computing_data_reduction        HKL2000
_computing_structure_solution    Yadokari
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[s²(Fo²)+(0.0784P)²+2.3657P] 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_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.15(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2571
_refine_ls_number_parameters     352
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1140
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.069
_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
C1 C 1.5038(6) 0.05312(12) 0.54579(15) 0.0203(6) Uani 1 1 d . . . . .
C2 C 1.5113(7) 0.01878(14) 0.49375(18) 0.0297(7) Uani 1 1 d . . . . .
H2 H 1.3858 0.0230 0.4586 0.036 Uiso 1 1 calc R U . . .
C3 C 1.6993(7) -0.02182(15) 0.49215(19) 0.0329(8) Uani 1 1 d . . . . .
H3 H 1.7006 -0.0450 0.4560 0.040 Uiso 1 1 calc R U . . .
C4 C 1.8838(7) -0.02883(15) 0.54239(19) 0.0302(7) Uani 1 1 d . . . . .
H4 H 2.0103 -0.0571 0.5415 0.036 Uiso 1 1 calc R U . . .
C5 C 1.8823(7) 0.00595(16) 0.59433(17) 0.0313(7) Uani 1 1 d . . . . .
H5 H 2.0108 0.0019 0.6289 0.038 Uiso 1 1 calc R U . . .
C6 C 1.6955(6) 0.04657(15) 0.59637(16) 0.0273(7) Uani 1 1 d . . . . .
H6 H 1.6972 0.0702 0.6323 0.033 Uiso 1 1 calc R U . . .
C7 C 1.3098(6) 0.09692(12) 0.54752(14) 0.0190(6) Uani 1 1 d . . . . .
C8 C 1.2748(6) 0.13748(13) 0.59274(15) 0.0231(6) Uani 1 1 d . . . . .
H8 H 1.3763 0.1420 0.6320 0.028 Uiso 1 1 calc R U . . .
C9 C 1.0646(6) 0.17035(13) 0.57029(15) 0.0217(6) Uani 1 1 d . . . . .
H9 H 0.9979 0.2012 0.5914 0.026 Uiso 1 1 calc R U . . .
C10 C 0.9715(5) 0.14952(12) 0.51142(14) 0.0174(6) Uani 1 1 d . . . . .
C11 C 0.7666(5) 0.16656(12) 0.46541(14) 0.0175(6) Uani 1 1 d . . . . .
C12 C 0.6041(6) 0.21061(12) 0.47383(14) 0.0182(6) Uani 1 1 d . . . . .
H12 H 0.6293 0.2334 0.5105 0.022 Uiso 1 1 calc R U . . .
C13 C 0.4012(5) 0.22096(12) 0.42714(14) 0.0175(6) Uani 1 1 d . . . . .
C14 C 0.2168(6) 0.26412(12) 0.43172(14) 0.0171(5) Uani 1 1 d . . . . .
C15 C 0.1845(6) 0.30345(13) 0.47901(14) 0.0203(6) Uani 1 1 d . . . . .
H15 H 0.2858 0.3070 0.5185 0.024 Uiso 1 1 calc R U . . .
C16 C -0.0259(6) 0.33635(13) 0.45667(15) 0.0212(6) Uani 1 1 d . . . . .
H16 H -0.0944 0.3663 0.4788 0.025 Uiso 1 1 calc R U . . .
C17 C -0.1184(6) 0.31786(12) 0.39648(15) 0.0181(6) Uani 1 1 d . . . . .
C18 C -0.3282(6) 0.33832(12) 0.35196(15) 0.0182(6) Uani 1 1 d . . . . .
C19 C -0.5011(6) 0.37732(13) 0.37193(16) 0.0214(6) Uani 1 1 d . . . . .
H19 H -0.4797 0.3907 0.4142 0.026 Uiso 1 1 calc R U . . .
C20 C -0.7039(6) 0.39666(13) 0.33053(16) 0.0230(6) Uani 1 1 d . . . . .
H20 H -0.8207 0.4230 0.3447 0.028 Uiso 1 1 calc R U . . .
C21 C -0.7367(6) 0.37771(13) 0.26873(17) 0.0258(7) Uani 1 1 d . . . . .
H21 H -0.8771 0.3906 0.2407 0.031 Uiso 1 1 calc R U . . .
C22 C -0.5638(7) 0.33980(15) 0.24790(16) 0.0264(7) Uani 1 1 d . . . . .
H22 H -0.5837 0.3273 0.2053 0.032 Uiso 1 1 calc R U . . .
C23 C -0.3605(6) 0.32011(13) 0.28955(15) 0.0234(6) Uani 1 1 d . . . . .
H23 H -0.2432 0.2940 0.2751 0.028 Uiso 1 1 calc R U . . .
C24 C 0.4612(6) 0.09939(12) 0.31958(15) 0.0203(6) Uani 1 1 d . . . . .
C25 C 0.5898(7) 0.07324(15) 0.27394(18) 0.0309(7) Uani 1 1 d . . . . .
H25 H 0.7391 0.0903 0.2607 0.037 Uiso 1 1 calc R U . . .
C26 C 0.5071(8) 0.02270(16) 0.2469(2) 0.0371(8) Uani 1 1 d . . . . .
H26 H 0.5992 0.0060 0.2155 0.045 Uiso 1 1 calc R U . . .
C27 C 0.2934(7) -0.00281(14) 0.2655(2) 0.0335(8) Uani 1 1 d . . . . .
H27 H 0.2390 -0.0377 0.2478 0.040 Uiso 1 1 calc R U . . .
C28 C 0.1580(7) 0.02216(16) 0.3097(2) 0.0345(8) Uani 1 1 d . . . . .
H28 H 0.0094 0.0046 0.3227 0.041 Uiso 1 1 calc R U . . .
C29 C 0.2381(7) 0.07339(14) 0.33571(17) 0.0284(7) Uani 1 1 d . . . . .
H29 H 0.1387 0.0910 0.3650 0.034 Uiso 1 1 calc R U . . .
C30 C 0.1167(8) 0.18497(15) 0.20575(18) 0.0338(8) Uani 1 1 d . . . . .
H30 H 0.2938 0.1940 0.2237 0.041 Uiso 1 1 calc R U . . .
H30A H 0.0105 0.1798 0.2413 0.041 Uiso 1 1 calc R U . . .
C31 C 0.1190(8) 0.13228(15) 0.16879(18) 0.0323(7) Uani 1 1 d . . . . .
H31 H -0.0538 0.1257 0.1466 0.039 Uiso 1 1 calc R U . . .
H31A H 0.1607 0.1007 0.1980 0.039 Uiso 1 1 calc R U . . .
Cl1 Cl -0.0099(2) 0.24175(4) 0.15696(6) 0.0487(3) Uani 1 1 d . . . . .
Cl2 Cl 0.3494(2) 0.13550(7) 0.11243(6) 0.0589(4) Uani 1 1 d . . . . .
O1 O 0.3655(4) 0.19048(9) 0.37514(10) 0.0192(4) Uani 1 1 d . . . . .
O2 O 0.7429(4) 0.13561(9) 0.41374(11) 0.0205(5) Uani 1 1 d . . . . .
F1 F 0.7276(3) 0.18575(7) 0.31872(9) 0.0228(4) Uani 1 1 d . . . . .
N1 N 1.1238(5) 0.10519(10) 0.49911(12) 0.0186(5) Uani 1 1 d . . . . .
H1 H 1.1037 0.0848 0.4645 0.022 Uiso 1 1 calc R U . . .
N2 N 0.0308(5) 0.27391(10) 0.38261(12) 0.0171(5) Uani 1 1 d . . . . .
H2A H 0.0108 0.2546 0.3473 0.021 Uiso 1 1 calc R U . . .
B1 B 0.5732(6) 0.15371(14) 0.35596(16) 0.0182(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.384(5) . ?
C1 C6 1.404(4) . ?
C1 C7 1.465(4) . ?
C2 C3 1.388(5) . ?
C3 C4 1.376(5) . ?
C4 C5 1.385(6) . ?
C5 C6 1.385(5) . ?
C7 N1 1.358(4) . ?
C7 C8 1.394(4) . ?
C8 C9 1.399(4) . ?
C9 C10 1.390(4) . ?
C10 N1 1.371(4) . ?
C10 C11 1.436(4) . ?
C11 O2 1.322(4) . ?
C11 C12 1.380(4) . ?
C12 C13 1.401(4) . ?
C13 O1 1.323(4) . ?
C13 C14 1.427(4) . ?
C14 N2 1.374(4) . ?
C14 C15 1.402(4) . ?
C15 C16 1.399(4) . ?
C16 C17 1.394(4) . ?
C17 N2 1.363(4) . ?
C17 C18 1.461(4) . ?
C18 C23 1.391(4) . ?
C18 C19 1.398(4) . ?
C19 C20 1.388(5) . ?
C20 C21 1.385(5) . ?
C21 C22 1.387(5) . ?
C22 C23 1.396(5) . ?
C24 C25 1.386(5) . ?
C24 C29 1.397(5) . ?
C24 B1 1.598(4) . ?
C25 C26 1.394(5) . ?
C26 C27 1.368(6) . ?
C27 C28 1.372(6) . ?
C28 C29 1.396(5) . ?
C30 C31 1.490(5) . ?
C30 Cl1 1.799(4) . ?
C31 Cl2 1.785(4) . ?
O1 B1 1.489(4) . ?
O2 B1 1.506(4) . ?
F1 B1 1.414(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.0(3) . . ?
C2 C1 C7 121.6(3) . . ?
C6 C1 C7 120.3(3) . . ?
C1 C2 C3 121.1(3) . . ?
C4 C3 C2 120.7(3) . . ?
C3 C4 C5 119.0(3) . . ?
C6 C5 C4 120.7(3) . . ?
C5 C6 C1 120.5(3) . . ?
N1 C7 C8 106.7(3) . . ?
N1 C7 C1 122.1(3) . . ?
C8 C7 C1 131.2(3) . . ?
C7 C8 C9 108.2(3) . . ?
C10 C9 C8 107.2(3) . . ?
N1 C10 C9 107.1(3) . . ?
N1 C10 C11 120.0(3) . . ?
C9 C10 C11 132.9(3) . . ?
O2 C11 C12 122.1(3) . . ?
O2 C11 C10 114.0(3) . . ?
C12 C11 C10 123.9(3) . . ?
C11 C12 C13 118.5(3) . . ?
O1 C13 C12 121.8(3) . . ?
O1 C13 C14 114.8(3) . . ?
C12 C13 C14 123.4(3) . . ?
N2 C14 C15 107.6(2) . . ?
N2 C14 C13 120.3(3) . . ?
C15 C14 C13 132.0(3) . . ?
C16 C15 C14 106.5(3) . . ?
C17 C16 C15 108.7(3) . . ?
N2 C17 C16 107.0(3) . . ?
N2 C17 C18 122.0(3) . . ?
C16 C17 C18 131.0(3) . . ?
C23 C18 C19 118.7(3) . . ?
C23 C18 C17 121.6(3) . . ?
C19 C18 C17 119.7(3) . . ?
C20 C19 C18 120.6(3) . . ?
C21 C20 C19 120.4(3) . . ?
C20 C21 C22 119.7(3) . . ?
C21 C22 C23 120.0(3) . . ?
C18 C23 C22 120.7(3) . . ?
C25 C24 C29 116.5(3) . . ?
C25 C24 B1 121.9(3) . . ?
C29 C24 B1 121.4(3) . . ?
C24 C25 C26 122.1(3) . . ?
C27 C26 C25 120.0(4) . . ?
C26 C27 C28 119.7(3) . . ?
C27 C28 C29 120.1(3) . . ?
C28 C29 C24 121.5(3) . . ?
C31 C30 Cl1 111.2(3) . . ?
C30 C31 Cl2 111.0(3) . . ?
C13 O1 B1 120.8(2) . . ?
C11 O2 B1 120.9(2) . . ?
C7 N1 C10 110.8(2) . . ?
C17 N2 C14 110.2(2) . . ?
F1 B1 O1 107.7(2) . . ?
F1 B1 O2 106.9(2) . . ?
O1 B1 O2 109.5(2) . . ?
F1 B1 C24 112.1(3) . . ?
O1 B1 C24 112.0(2) . . ?
O2 B1 C24 108.5(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
C6 C1 C2 C3 1.4(5) . . . . ?
C7 C1 C2 C3 178.7(3) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C2 C3 C4 C5 -1.2(6) . . . . ?
C3 C4 C5 C6 1.2(6) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
C2 C1 C6 C5 -1.4(5) . . . . ?
C7 C1 C6 C5 -178.7(3) . . . . ?
C2 C1 C7 N1 1.8(5) . . . . ?
C6 C1 C7 N1 178.9(3) . . . . ?
C2 C1 C7 C8 -176.2(3) . . . . ?
C6 C1 C7 C8 0.9(5) . . . . ?
N1 C7 C8 C9 -0.2(4) . . . . ?
C1 C7 C8 C9 178.0(3) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
C8 C9 C10 N1 -0.1(3) . . . . ?
C8 C9 C10 C11 -178.0(3) . . . . ?
N1 C10 C11 O2 0.9(4) . . . . ?
C9 C10 C11 O2 178.7(3) . . . . ?
N1 C10 C11 C12 180.0(3) . . . . ?
C9 C10 C11 C12 -2.3(5) . . . . ?
O2 C11 C12 C13 2.9(4) . . . . ?
C10 C11 C12 C13 -176.0(3) . . . . ?
C11 C12 C13 O1 -1.4(4) . . . . ?
C11 C12 C13 C14 177.9(3) . . . . ?
O1 C13 C14 N2 -4.2(4) . . . . ?
C12 C13 C14 N2 176.5(3) . . . . ?
O1 C13 C14 C15 178.0(3) . . . . ?
C12 C13 C14 C15 -1.3(5) . . . . ?
N2 C14 C15 C16 0.4(3) . . . . ?
C13 C14 C15 C16 178.4(3) . . . . ?
C14 C15 C16 C17 -0.7(4) . . . . ?
C15 C16 C17 N2 0.8(3) . . . . ?
C15 C16 C17 C18 -178.3(3) . . . . ?
N2 C17 C18 C23 -10.6(4) . . . . ?
C16 C17 C18 C23 168.3(3) . . . . ?
N2 C17 C18 C19 169.7(3) . . . . ?
C16 C17 C18 C19 -11.4(5) . . . . ?
C23 C18 C19 C20 1.2(4) . . . . ?
C17 C18 C19 C20 -179.1(3) . . . . ?
C18 C19 C20 C21 -0.3(5) . . . . ?
C19 C20 C21 C22 -0.9(5) . . . . ?
C20 C21 C22 C23 1.2(5) . . . . ?
C19 C18 C23 C22 -0.9(4) . . . . ?
C17 C18 C23 C22 179.4(3) . . . . ?
C21 C22 C23 C18 -0.3(5) . . . . ?
C29 C24 C25 C26 -2.1(5) . . . . ?
B1 C24 C25 C26 173.1(3) . . . . ?
C24 C25 C26 C27 -0.3(6) . . . . ?
C25 C26 C27 C28 1.5(6) . . . . ?
C26 C27 C28 C29 0.0(6) . . . . ?
C27 C28 C29 C24 -2.6(5) . . . . ?
C25 C24 C29 C28 3.6(5) . . . . ?
B1 C24 C29 C28 -171.7(3) . . . . ?
Cl1 C30 C31 Cl2 68.8(3) . . . . ?
C12 C13 O1 B1 -15.8(4) . . . . ?
C14 C13 O1 B1 164.8(3) . . . . ?
C12 C11 O2 B1 12.7(4) . . . . ?
C10 C11 O2 B1 -168.3(2) . . . . ?
C8 C7 N1 C10 0.2(3) . . . . ?
C1 C7 N1 C10 -178.2(3) . . . . ?
C9 C10 N1 C7 -0.1(3) . . . . ?
C11 C10 N1 C7 178.2(3) . . . . ?
C16 C17 N2 C14 -0.6(3) . . . . ?
C18 C17 N2 C14 178.6(3) . . . . ?
C15 C14 N2 C17 0.1(3) . . . . ?
C13 C14 N2 C17 -178.1(2) . . . . ?
C13 O1 B1 F1 -87.9(3) . . . . ?
C13 O1 B1 O2 28.0(4) . . . . ?
C13 O1 B1 C24 148.4(3) . . . . ?
C11 O2 B1 F1 89.9(3) . . . . ?
C11 O2 B1 O1 -26.5(4) . . . . ?
C11 O2 B1 C24 -149.1(3) . . . . ?
C25 C24 B1 F1 28.8(4) . . . . ?
C29 C24 B1 F1 -156.2(3) . . . . ?
C25 C24 B1 O1 150.1(3) . . . . ?
C29 C24 B1 O1 -35.0(4) . . . . ?
C25 C24 B1 O2 -88.9(4) . . . . ?
C29 C24 B1 O2 86.1(3) . . . . ?

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
C8 H8 Cl1 0.95 2.89 3.353(3) 111.0 4_655
C16 H16 Cl2 0.95 2.89 3.505(3) 123.9 4_455
C30 H30A F1 0.99 2.33 3.301(4) 168.2 1_455
N2 H2A F1 0.88 2.26 2.901(3) 129.3 1_455
C8 H8 Cl1 0.95 2.89 3.353(3) 111.0 4_655
C16 H16 Cl2 0.95 2.89 3.505(3) 123.9 4_455
C30 H30A F1 0.99 2.33 3.301(4) 168.2 1_455
N2 H2A F1 0.88 2.26 2.901(3) 129.3 1_455
C8 H8 Cl1 0.95 2.89 3.353(3) 111.0 4_655
C16 H16 Cl2 0.95 2.89 3.505(3) 123.9 4_455
C30 H30A F1 0.99 2.33 3.301(4) 168.2 1_455
N2 H2A F1 0.88 2.26 2.901(3) 129.3 1_455
C8 H8 Cl1 0.95 2.89 3.353(3) 111.0 4_655
C16 H16 Cl2 0.95 2.89 3.505(3) 123.9 4_455
C30 H30A F1 0.99 2.33 3.301(4) 168.2 1_455
N2 H2A F1 0.88 2.26 2.901(3) 129.3 1_455
C8 H8 Cl1 0.95 2.89 3.353(3) 111.0 4_655
C16 H16 Cl2 0.95 2.89 3.505(3) 123.9 4_455
C30 H30A F1 0.99 2.33 3.301(4) 168.2 1_455
N2 H2A F1 0.88 2.26 2.901(3) 129.3 1_455
C8 H8 Cl1 0.95 2.89 3.353(3) 111.0 4_655
C16 H16 Cl2 0.95 2.89 3.505(3) 123.9 4_455
C30 H30A F1 0.99 2.33 3.301(4) 168.2 1_455
N2 H2A F1 0.88 2.26 2.901(3) 129.3 1_455

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.439
_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_51120m
_database_code_depnum_ccdc_archive 'CCDC 2086721'
loop_
_audit_author_name
_audit_author_address
'Nobuhiro Yasuda'
;Japan Synchrotron Radiation Research Institute
Japan
;
_audit_update_record             
;
2021-05-29 deposited with the CCDC.	2021-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 B F N2 O4, 0.5(O)'
_chemical_formula_sum            'C18 H14 B F N2 O4.50'
_chemical_formula_weight         360.12

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

_space_group_crystal_system      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                   8.886(3)
_cell_length_b                   11.226(4)
_cell_length_c                   17.787(4)
_cell_angle_alpha                90.896(8)
_cell_angle_beta                 98.176(6)
_cell_angle_gamma                110.456(15)
_cell_volume                     1641.5(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    21553
_cell_measurement_theta_min      6.772
_cell_measurement_theta_max      68.411

_exptl_crystal_description       Prism
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.946
_shelx_estimated_absorpt_T_min   0.692
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.706
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            21553
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         6.772
_diffrn_reflns_theta_max         68.411
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             5833
_reflns_number_gt                4944
_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       'Rapid Auto(Rigaku)'
_computing_cell_refinement       'Rapid Auto(Rigaku)'
_computing_data_reduction        'Rapid Auto(Rigaku)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1136P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0040(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5833
_refine_ls_number_parameters     479
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1500
_refine_ls_wR_factor_gt          0.1467
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
C1 C -0.1489(2) 0.85256(19) 0.25434(10) 0.0244(4) Uani 1 1 d . . . . .
H1 H -0.1735 0.7930 0.2922 0.029 Uiso 1 1 calc R U . . .
C2 C -0.2568(2) 0.89973(19) 0.21310(11) 0.0272(4) Uani 1 1 d . . . . .
H2 H -0.3680 0.8796 0.2179 0.033 Uiso 1 1 calc R U . . .
C3 C -0.1724(2) 0.98219(19) 0.16330(10) 0.0232(4) Uani 1 1 d . . . . .
H3 H -0.2159 1.0282 0.1274 0.028 Uiso 1 1 calc R U . . .
C4 C -0.0126(2) 0.98520(17) 0.17547(9) 0.0190(4) Uani 1 1 d . . . . .
C5 C 0.12447(19) 1.05965(17) 0.14266(9) 0.0177(4) Uani 1 1 d . . . . .
C6 C 0.1119(2) 1.13228(18) 0.08170(10) 0.0217(4) Uani 1 1 d . . . . .
H6 H 0.0093 1.1366 0.0613 0.026 Uiso 1 1 calc R U . . .
C7 C 0.2488(2) 1.19880(17) 0.05038(9) 0.0183(4) Uani 1 1 d . . . . .
C8 C 0.2478(2) 1.27167(17) -0.01416(9) 0.0199(4) Uani 1 1 d . . . . .
C9 C 0.1221(2) 1.28967(18) -0.06329(10) 0.0233(4) Uani 1 1 d . . . . .
H9 H 0.0094 1.2535 -0.0603 0.028 Uiso 1 1 calc R U . . .
C10 C 0.1917(2) 1.3703(2) -0.11751(10) 0.0275(4) Uani 1 1 d . . . . .
H10 H 0.1353 1.3993 -0.1584 0.033 Uiso 1 1 calc R U . . .
C11 C 0.3580(2) 1.4004(2) -0.10088(10) 0.0292(5) Uani 1 1 d . . . . .
H11 H 0.4362 1.4541 -0.1285 0.035 Uiso 1 1 calc R U . . .
C12 C 0.53687(19) 1.24287(17) 0.21616(9) 0.0186(4) Uani 1 1 d . . . . .
C13 C 0.6755(2) 1.23292(18) 0.25968(10) 0.0217(4) Uani 1 1 d . . . . .
H13 H 0.7006 1.1584 0.2525 0.026 Uiso 1 1 calc R U . . .
C14 C 0.7771(2) 1.32885(18) 0.31303(10) 0.0227(4) Uani 1 1 d . . . . .
H14 H 0.8699 1.3190 0.3421 0.027 Uiso 1 1 calc R U . . .
C15 C 0.7439(2) 1.43939(18) 0.32426(9) 0.0203(4) Uani 1 1 d . . . . .
C16 C 0.8559(2) 1.54595(18) 0.37850(9) 0.0207(4) Uani 1 1 d . . . . .
C17 C 0.6043(2) 1.45091(18) 0.28266(10) 0.0217(4) Uani 1 1 d . . . . .
H17 H 0.5786 1.5250 0.2905 0.026 Uiso 1 1 calc R U . . .
C18 C 0.5041(2) 1.35382(18) 0.23008(10) 0.0214(4) Uani 1 1 d . . . . .
H18 H 0.4094 1.3626 0.2023 0.026 Uiso 1 1 calc R U . . .
N1 N -0.00254(17) 0.90521(15) 0.23179(8) 0.0209(3) Uani 1 1 d . . . . .
H1A H 0.0859 0.8904 0.2504 0.025 Uiso 1 1 calc R U . . .
N2 N 0.39049(18) 1.34091(16) -0.03906(8) 0.0238(4) Uani 1 1 d . . . . .
H2A H 0.4882 1.3456 -0.0178 0.029 Uiso 1 1 calc R U . . .
O1 O 0.26535(14) 1.05504(12) 0.17448(6) 0.0207(3) Uani 1 1 d . . . . .
O2 O 0.39330(14) 1.19868(13) 0.08014(6) 0.0217(3) Uani 1 1 d . . . . .
O3 O 0.98351(15) 1.52381(12) 0.41245(7) 0.0258(3) Uani 1 1 d . . . . .
H3A H 1.0422 1.5867 0.4423 0.039 Uiso 1 1 calc R U . . .
O4 O 0.83113(14) 1.64512(13) 0.39004(7) 0.0247(3) Uani 1 1 d . . . . .
B1 B 0.4240(2) 1.1360(2) 0.15113(11) 0.0191(4) Uani 1 1 d . . . . .
F1 F 0.49897(11) 1.05050(10) 0.13252(5) 0.0224(3) Uani 1 1 d . . . . .
C19 C 0.2014(3) 0.2689(2) 0.40891(13) 0.0363(5) Uani 1 1 d . . . . .
H19 H 0.2202 0.2381 0.4575 0.044 Uiso 1 1 calc R U . . .
C20 C 0.1217(3) 0.1938(2) 0.34298(12) 0.0346(5) Uani 1 1 d . . . . .
H20 H 0.0755 0.1034 0.3379 0.042 Uiso 1 1 calc R U . . .
C21 C 0.1221(2) 0.27648(19) 0.28515(11) 0.0289(5) Uani 1 1 d . . . . .
H21 H 0.0769 0.2525 0.2331 0.035 Uiso 1 1 calc R U . . .
C22 C 0.2005(2) 0.40011(18) 0.31751(10) 0.0229(4) Uani 1 1 d . . . . .
C23 C 0.2337(2) 0.52005(17) 0.28575(10) 0.0197(4) Uani 1 1 d . . . . .
C24 C 0.2006(2) 0.53297(17) 0.20755(10) 0.0209(4) Uani 1 1 d . . . . .
H24 H 0.1382 0.4609 0.1736 0.025 Uiso 1 1 calc R U . . .
C25 C 0.26075(19) 0.65287(17) 0.18076(9) 0.0188(4) Uani 1 1 d . . . . .
C26 C 0.2586(2) 0.67507(17) 0.10114(10) 0.0201(4) Uani 1 1 d . . . . .
C27 C 0.2037(2) 0.59369(19) 0.03563(10) 0.0231(4) Uani 1 1 d . . . . .
H27 H 0.1559 0.5034 0.0332 0.028 Uiso 1 1 calc R U . . .
C28 C 0.2323(2) 0.6699(2) -0.02642(10) 0.0265(4) Uani 1 1 d . . . . .
H28 H 0.2063 0.6406 -0.0787 0.032 Uiso 1 1 calc R U . . .
C29 C 0.3046(2) 0.7946(2) 0.00224(10) 0.0248(4) Uani 1 1 d . . . . .
H29 H 0.3385 0.8668 -0.0269 0.030 Uiso 1 1 calc R U . . .
C30 C 0.4485(2) 0.86062(18) 0.36079(9) 0.0197(4) Uani 1 1 d . . . . .
C31 C 0.5932(2) 0.84783(18) 0.39649(10) 0.0228(4) Uani 1 1 d . . . . .
H31 H 0.6081 0.7686 0.3908 0.027 Uiso 1 1 calc R U . . .
C32 C 0.7145(2) 0.94871(18) 0.43979(10) 0.0233(4) Uani 1 1 d . . . . .
H32 H 0.8123 0.9387 0.4625 0.028 Uiso 1 1 calc R U . . .
C33 C 0.6934(2) 1.06437(18) 0.45007(9) 0.0212(4) Uani 1 1 d . . . . .
C34 C 0.8183(2) 1.17253(18) 0.49757(9) 0.0218(4) Uani 1 1 d . . . . .
C35 C 0.5512(2) 1.07929(19) 0.41498(10) 0.0234(4) Uani 1 1 d . . . . .
H35 H 0.5363 1.1585 0.4211 0.028 Uiso 1 1 calc R U . . .
C36 C 0.4317(2) 0.97843(18) 0.37129(10) 0.0231(4) Uani 1 1 d . . . . .
H36 H 0.3353 0.9897 0.3477 0.028 Uiso 1 1 calc R U . . .
N3 N 0.2485(2) 0.39229(16) 0.39389(9) 0.0273(4) Uani 1 1 d . . . . .
H3B H 0.3013 0.4574 0.4273 0.033 Uiso 1 1 calc R U . . .
N4 N 0.31910(17) 0.79689(15) 0.07900(8) 0.0215(3) Uani 1 1 d . . . . .
H4 H 0.3611 0.8662 0.1101 0.026 Uiso 1 1 calc R U . . .
O5 O 0.30608(14) 0.62057(12) 0.33376(6) 0.0206(3) Uani 1 1 d . . . . .
O6 O 0.33032(14) 0.75560(11) 0.22724(6) 0.0201(3) Uani 1 1 d . . . . .
B2 B 0.3078(2) 0.7475(2) 0.30964(11) 0.0193(4) Uani 1 1 d . . . . .
F2 F 0.15200(11) 0.75261(10) 0.31173(5) 0.0225(3) Uani 1 1 d . . . . .
O7 O 0.94321(15) 1.14791(13) 0.53367(7) 0.0283(3) Uani 1 1 d . . . . .
H7 H 1.0084 1.2138 0.5593 0.043 Uiso 1 1 calc R U . . .
O8 O 0.80629(15) 1.27789(13) 0.50371(7) 0.0260(3) Uani 1 1 d . . . . .
O9 O 0.41144(19) 0.59116(16) 0.50729(8) 0.0414(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
C1 N1 1.349(2) . ?
C1 C2 1.380(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.390(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(2) . ?
C3 H3 0.9500 . ?
C4 N1 1.370(2) . ?
C4 C5 1.424(2) . ?
C5 O1 1.317(2) . ?
C5 C6 1.382(3) . ?
C6 C7 1.385(3) . ?
C6 H6 0.9500 . ?
C7 O2 1.318(2) . ?
C7 C8 1.421(3) . ?
C8 N2 1.374(2) . ?
C8 C9 1.392(3) . ?
C9 C10 1.392(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9500 . ?
C11 N2 1.344(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.399(3) . ?
C12 C18 1.401(3) . ?
C12 B1 1.603(3) . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(3) . ?
C14 H14 0.9500 . ?
C15 C17 1.399(3) . ?
C15 C16 1.487(2) . ?
C16 O4 1.228(2) . ?
C16 O3 1.311(2) . ?
C17 C18 1.382(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N1 H1A 0.8800 . ?
N2 H2A 0.8800 . ?
O1 B1 1.506(2) . ?
O2 B1 1.492(2) . ?
O3 H3A 0.8400 . ?
B1 F1 1.406(2) . ?
C19 N3 1.343(3) . ?
C19 C20 1.379(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.396(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(3) . ?
C21 H21 0.9500 . ?
C22 N3 1.379(2) . ?
C22 C23 1.419(3) . ?
C23 O5 1.313(2) . ?
C23 C24 1.401(3) . ?
C24 C25 1.383(3) . ?
C24 H24 0.9500 . ?
C25 O6 1.312(2) . ?
C25 C26 1.440(2) . ?
C26 N4 1.370(3) . ?
C26 C27 1.387(2) . ?
C27 C28 1.404(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.374(3) . ?
C28 H28 0.9500 . ?
C29 N4 1.352(2) . ?
C29 H29 0.9500 . ?
C30 C36 1.394(3) . ?
C30 C31 1.406(3) . ?
C30 B2 1.592(3) . ?
C31 C32 1.386(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.388(3) . ?
C32 H32 0.9500 . ?
C33 C35 1.394(3) . ?
C33 C34 1.476(2) . ?
C34 O8 1.229(2) . ?
C34 O7 1.318(2) . ?
C35 C36 1.382(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
N3 H3B 0.8800 . ?
N4 H4 0.8800 . ?
O5 B2 1.490(3) . ?
O6 B2 1.507(2) . ?
B2 F2 1.411(2) . ?
O7 H7 0.8400 . ?

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
N1 C1 C2 108.51(17) . . ?
N1 C1 H1 125.7 . . ?
C2 C1 H1 125.7 . . ?
C1 C2 C3 107.21(16) . . ?
C1 C2 H2 126.4 . . ?
C3 C2 H2 126.4 . . ?
C2 C3 C4 107.69(17) . . ?
C2 C3 H3 126.2 . . ?
C4 C3 H3 126.2 . . ?
N1 C4 C3 106.92(15) . . ?
N1 C4 C5 122.81(15) . . ?
C3 C4 C5 130.16(18) . . ?
O1 C5 C6 121.85(15) . . ?
O1 C5 C4 115.44(16) . . ?
C6 C5 C4 122.71(15) . . ?
C5 C6 C7 120.03(16) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
O2 C7 C6 120.84(17) . . ?
O2 C7 C8 114.74(15) . . ?
C6 C7 C8 124.43(16) . . ?
N2 C8 C9 106.99(16) . . ?
N2 C8 C7 120.77(15) . . ?
C9 C8 C7 132.23(16) . . ?
C10 C9 C8 107.53(17) . . ?
C10 C9 H9 126.2 . . ?
C8 C9 H9 126.2 . . ?
C11 C10 C9 107.28(17) . . ?
C11 C10 H10 126.4 . . ?
C9 C10 H10 126.4 . . ?
N2 C11 C10 108.57(17) . . ?
N2 C11 H11 125.7 . . ?
C10 C11 H11 125.7 . . ?
C13 C12 C18 116.68(16) . . ?
C13 C12 B1 122.20(15) . . ?
C18 C12 B1 121.08(16) . . ?
C14 C13 C12 121.79(16) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 120.29(17) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C17 119.18(16) . . ?
C14 C15 C16 121.01(16) . . ?
C17 C15 C16 119.79(16) . . ?
O4 C16 O3 123.42(16) . . ?
O4 C16 C15 123.06(16) . . ?
O3 C16 C15 113.51(15) . . ?
C18 C17 C15 119.59(16) . . ?
C18 C17 H17 120.2 . . ?
C15 C17 H17 120.2 . . ?
C17 C18 C12 122.43(16) . . ?
C17 C18 H18 118.8 . . ?
C12 C18 H18 118.8 . . ?
C1 N1 C4 109.66(15) . . ?
C1 N1 H1A 125.2 . . ?
C4 N1 H1A 125.2 . . ?
C11 N2 C8 109.62(15) . . ?
C11 N2 H2A 125.2 . . ?
C8 N2 H2A 125.2 . . ?
C5 O1 B1 122.37(15) . . ?
C7 O2 B1 123.64(13) . . ?
C16 O3 H3A 109.5 . . ?
F1 B1 O2 106.70(13) . . ?
F1 B1 O1 105.59(15) . . ?
O2 B1 O1 110.30(14) . . ?
F1 B1 C12 112.09(14) . . ?
O2 B1 C12 109.21(15) . . ?
O1 B1 C12 112.75(13) . . ?
N3 C19 C20 109.55(19) . . ?
N3 C19 H19 125.2 . . ?
C20 C19 H19 125.2 . . ?
C19 C20 C21 106.67(19) . . ?
C19 C20 H20 126.7 . . ?
C21 C20 H20 126.7 . . ?
C22 C21 C20 107.62(18) . . ?
C22 C21 H21 126.2 . . ?
C20 C21 H21 126.2 . . ?
N3 C22 C21 107.43(18) . . ?
N3 C22 C23 120.87(17) . . ?
C21 C22 C23 131.69(18) . . ?
O5 C23 C24 120.91(17) . . ?
O5 C23 C22 115.98(16) . . ?
C24 C23 C22 123.02(16) . . ?
C25 C24 C23 118.63(16) . . ?
C25 C24 H24 120.7 . . ?
C23 C24 H24 120.7 . . ?
O6 C25 C24 121.66(15) . . ?
O6 C25 C26 114.78(16) . . ?
C24 C25 C26 123.52(15) . . ?
N4 C26 C27 107.36(16) . . ?
N4 C26 C25 120.09(15) . . ?
C27 C26 C25 132.55(18) . . ?
C26 C27 C28 107.10(17) . . ?
C26 C27 H27 126.5 . . ?
C28 C27 H27 126.5 . . ?
C29 C28 C27 107.54(15) . . ?
C29 C28 H28 126.2 . . ?
C27 C28 H28 126.2 . . ?
N4 C29 C28 108.24(18) . . ?
N4 C29 H29 125.9 . . ?
C28 C29 H29 125.9 . . ?
C36 C30 C31 117.26(16) . . ?
C36 C30 B2 120.17(16) . . ?
C31 C30 B2 122.57(16) . . ?
C32 C31 C30 121.20(17) . . ?
C32 C31 H31 119.4 . . ?
C30 C31 H31 119.4 . . ?
C31 C32 C33 120.23(17) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C32 C33 C35 119.51(16) . . ?
C32 C33 C34 121.55(16) . . ?
C35 C33 C34 118.94(16) . . ?
O8 C34 O7 122.22(16) . . ?
O8 C34 C33 122.47(16) . . ?
O7 C34 C33 115.31(16) . . ?
C36 C35 C33 119.75(17) . . ?
C36 C35 H35 120.1 . . ?
C33 C35 H35 120.1 . . ?
C35 C36 C30 122.03(17) . . ?
C35 C36 H36 119.0 . . ?
C30 C36 H36 119.0 . . ?
C19 N3 C22 108.72(17) . . ?
C19 N3 H3B 125.6 . . ?
C22 N3 H3B 125.6 . . ?
C29 N4 C26 109.75(15) . . ?
C29 N4 H4 125.1 . . ?
C26 N4 H4 125.1 . . ?
C23 O5 B2 119.09(14) . . ?
C25 O6 B2 118.80(14) . . ?
F2 B2 O5 107.96(15) . . ?
F2 B2 O6 105.67(14) . . ?
O5 B2 O6 108.44(13) . . ?
F2 B2 C30 112.61(13) . . ?
O5 B2 C30 111.56(15) . . ?
O6 B2 C30 110.35(14) . . ?
C34 O7 H7 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.9(2) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C2 C3 C4 N1 0.09(19) . . . . ?
C2 C3 C4 C5 -175.93(17) . . . . ?
N1 C4 C5 O1 -5.5(2) . . . . ?
C3 C4 C5 O1 169.94(16) . . . . ?
N1 C4 C5 C6 174.58(15) . . . . ?
C3 C4 C5 C6 -9.9(3) . . . . ?
O1 C5 C6 C7 2.6(2) . . . . ?
C4 C5 C6 C7 -177.50(14) . . . . ?
C5 C6 C7 O2 -3.1(2) . . . . ?
C5 C6 C7 C8 177.23(15) . . . . ?
O2 C7 C8 N2 -3.4(2) . . . . ?
C6 C7 C8 N2 176.22(15) . . . . ?
O2 C7 C8 C9 175.79(16) . . . . ?
C6 C7 C8 C9 -4.5(3) . . . . ?
N2 C8 C9 C10 -0.04(18) . . . . ?
C7 C8 C9 C10 -179.35(17) . . . . ?
C8 C9 C10 C11 -0.03(19) . . . . ?
C9 C10 C11 N2 0.1(2) . . . . ?
C18 C12 C13 C14 -1.1(3) . . . . ?
B1 C12 C13 C14 176.56(16) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C13 C14 C15 C17 1.8(3) . . . . ?
C13 C14 C15 C16 -176.97(16) . . . . ?
C14 C15 C16 O4 179.96(16) . . . . ?
C17 C15 C16 O4 1.2(3) . . . . ?
C14 C15 C16 O3 0.2(2) . . . . ?
C17 C15 C16 O3 -178.61(15) . . . . ?
C14 C15 C17 C18 -1.4(3) . . . . ?
C16 C15 C17 C18 177.38(15) . . . . ?
C15 C17 C18 C12 -0.3(3) . . . . ?
C13 C12 C18 C17 1.5(3) . . . . ?
B1 C12 C18 C17 -176.18(16) . . . . ?
C2 C1 N1 C4 -0.8(2) . . . . ?
C3 C4 N1 C1 0.46(19) . . . . ?
C5 C4 N1 C1 176.84(14) . . . . ?
C10 C11 N2 C8 -0.1(2) . . . . ?
C9 C8 N2 C11 0.10(19) . . . . ?
C7 C8 N2 C11 179.50(15) . . . . ?
C6 C5 O1 B1 5.0(2) . . . . ?
C4 C5 O1 B1 -174.92(14) . . . . ?
C6 C7 O2 B1 -4.1(2) . . . . ?
C8 C7 O2 B1 175.59(14) . . . . ?
C7 O2 B1 F1 124.49(15) . . . . ?
C7 O2 B1 O1 10.3(2) . . . . ?
C7 O2 B1 C12 -114.15(16) . . . . ?
C5 O1 B1 F1 -125.56(15) . . . . ?
C5 O1 B1 O2 -10.7(2) . . . . ?
C5 O1 B1 C12 111.73(17) . . . . ?
C13 C12 B1 F1 -13.2(2) . . . . ?
C18 C12 B1 F1 164.37(15) . . . . ?
C13 C12 B1 O2 -131.20(16) . . . . ?
C18 C12 B1 O2 46.3(2) . . . . ?
C13 C12 B1 O1 105.82(18) . . . . ?
C18 C12 B1 O1 -76.6(2) . . . . ?
N3 C19 C20 C21 0.5(2) . . . . ?
C19 C20 C21 C22 -0.7(2) . . . . ?
C20 C21 C22 N3 0.6(2) . . . . ?
C20 C21 C22 C23 -179.30(18) . . . . ?
N3 C22 C23 O5 -2.5(2) . . . . ?
C21 C22 C23 O5 177.43(17) . . . . ?
N3 C22 C23 C24 174.09(15) . . . . ?
C21 C22 C23 C24 -6.0(3) . . . . ?
O5 C23 C24 C25 6.7(2) . . . . ?
C22 C23 C24 C25 -169.74(15) . . . . ?
C23 C24 C25 O6 -8.2(2) . . . . ?
C23 C24 C25 C26 169.18(15) . . . . ?
O6 C25 C26 N4 -3.0(2) . . . . ?
C24 C25 C26 N4 179.38(15) . . . . ?
O6 C25 C26 C27 177.14(17) . . . . ?
C24 C25 C26 C27 -0.4(3) . . . . ?
N4 C26 C27 C28 -0.26(19) . . . . ?
C25 C26 C27 C28 179.58(17) . . . . ?
C26 C27 C28 C29 0.6(2) . . . . ?
C27 C28 C29 N4 -0.7(2) . . . . ?
C36 C30 C31 C32 -0.5(3) . . . . ?
B2 C30 C31 C32 179.05(16) . . . . ?
C30 C31 C32 C33 1.4(3) . . . . ?
C31 C32 C33 C35 -1.6(3) . . . . ?
C31 C32 C33 C34 178.30(16) . . . . ?
C32 C33 C34 O8 175.57(16) . . . . ?
C35 C33 C34 O8 -4.6(3) . . . . ?
C32 C33 C34 O7 -5.1(2) . . . . ?
C35 C33 C34 O7 174.78(15) . . . . ?
C32 C33 C35 C36 0.9(3) . . . . ?
C34 C33 C35 C36 -178.97(16) . . . . ?
C33 C35 C36 C30 0.0(3) . . . . ?
C31 C30 C36 C35 -0.2(3) . . . . ?
B2 C30 C36 C35 -179.73(16) . . . . ?
C20 C19 N3 C22 -0.1(2) . . . . ?
C21 C22 N3 C19 -0.3(2) . . . . ?
C23 C22 N3 C19 179.62(16) . . . . ?
C28 C29 N4 C26 0.54(19) . . . . ?
C27 C26 N4 C29 -0.17(19) . . . . ?
C25 C26 N4 C29 179.97(14) . . . . ?
C24 C23 O5 B2 18.6(2) . . . . ?
C22 C23 O5 B2 -164.73(14) . . . . ?
C24 C25 O6 B2 -15.3(2) . . . . ?
C26 C25 O6 B2 167.07(14) . . . . ?
C23 O5 B2 F2 75.88(16) . . . . ?
C23 O5 B2 O6 -38.16(19) . . . . ?
C23 O5 B2 C30 -159.88(13) . . . . ?
C25 O6 B2 F2 -79.07(18) . . . . ?
C25 O6 B2 O5 36.47(19) . . . . ?
C25 O6 B2 C30 158.94(14) . . . . ?
C36 C30 B2 F2 -30.8(2) . . . . ?
C31 C30 B2 F2 149.63(16) . . . . ?
C36 C30 B2 O5 -152.42(15) . . . . ?
C31 C30 B2 O5 28.1(2) . . . . ?
C36 C30 B2 O6 86.97(18) . . . . ?
C31 C30 B2 O6 -92.6(2) . . . . ?

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
N3 H3B O9 0.88 1.94 2.814(2) 175.2 .
C1 H1 O4 0.95 2.43 3.360(3) 166.2 1_445
C2 H2 O6 0.95 2.58 3.503(2) 162.6 1_455
N1 H1A F2 0.88 2.11 2.830(2) 139.1 .
O3 H3A O8 0.84 1.79 2.6202(19) 170.1 2_786
C29 H29 F1 0.95 2.52 3.319(2) 141.3 2_675
N4 H4 F1 0.88 2.00 2.805(2) 151.3 .
O7 H7 O4 0.84 1.83 2.6705(19) 173.4 2_786

_refine_diff_density_max         0.581
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.072



####################################################################### 
# 
# 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_tm-1-2
_database_code_depnum_ccdc_archive 'CCDC 2086726'
loop_
_audit_author_name
_audit_author_address
'Nobuhiro Yasuda'
;Japan Synchrotron Radiation Research Institute
Japan
;
_audit_update_record             
;
2021-05-29 deposited with the CCDC.	2021-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H21 B N2 O4, 1.5(C3 H6 O)'
_chemical_formula_sum            'C34.50 H30 B N2 O5.50'
_chemical_formula_weight         571.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0021 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0007 0.0011 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0000 0.0002 '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                   11.069(3)
_cell_length_b                   30.848(9)
_cell_length_c                   17.795(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.689(7)
_cell_angle_gamma                90
_cell_volume                     6074(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    171814
_cell_measurement_theta_min      0.794
_cell_measurement_theta_max      16.115

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             2400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.037
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   1.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6604
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
PROCESS-AUTO (1998). Automatic Data Acquisition and Processing Package
for 2D image data. Rigaku Corporation, Tokyo, Japan.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.4275
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'BL02B1 beamline SPring-8'
_diffrn_measurement_device_type  'Pilatus3 CdTe 1M'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            171814
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_av_R_equivalents  0.1526
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         0.794
_diffrn_reflns_theta_max         16.115
_diffrn_reflns_theta_full        14.862
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             13739
_reflns_number_gt                8299
_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       'Rapid Auto(Rigaku)'
_computing_cell_refinement       'Rapid Auto(Rigaku)'
_computing_data_reduction        'Rapid Auto(Rigaku)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)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         13739
_refine_ls_number_parameters     781
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0737
_refine_ls_wR_factor_ref         0.2130
_refine_ls_wR_factor_gt          0.1903
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_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
C1 C -0.0443(3) 0.70216(10) 0.39892(14) 0.0614(7) Uani 1 1 d . . . . .
H1 H 0.0229 0.7060 0.4327 0.074 Uiso 1 1 calc R U . . .
C2 C -0.0712(3) 0.73394(10) 0.34473(16) 0.0685(8) Uani 1 1 d . . . . .
H2 H -0.0217 0.7590 0.3416 0.082 Uiso 1 1 calc R U . . .
C3 C -0.1711(3) 0.72889(11) 0.29502(16) 0.0708(9) Uani 1 1 d . . . . .
H3 H -0.1891 0.7504 0.2582 0.085 Uiso 1 1 calc R U . . .
C4 C -0.2433(3) 0.69234(11) 0.29991(15) 0.0663(8) Uani 1 1 d . . . . .
H4 H -0.3111 0.6889 0.2664 0.080 Uiso 1 1 calc R U . . .
C5 C -0.2171(3) 0.66046(11) 0.35378(15) 0.0611(7) Uani 1 1 d . . . . .
H5 H -0.2676 0.6357 0.3570 0.073 Uiso 1 1 calc R U . . .
C6 C -0.1148(3) 0.66499(10) 0.40389(13) 0.0546(7) Uani 1 1 d . . . . .
C7 C -0.0864(2) 0.62898(10) 0.45604(13) 0.0540(6) Uani 1 1 d . . . . .
C8 C -0.1317(3) 0.58671(10) 0.45571(14) 0.0586(7) Uani 1 1 d . . . . .
H8 H -0.1920 0.5755 0.4219 0.070 Uiso 1 1 calc R U . . .
C9 C -0.0725(2) 0.56370(10) 0.51418(15) 0.0574(7) Uani 1 1 d . . . . .
H9 H -0.0850 0.5341 0.5267 0.069 Uiso 1 1 calc R U . . .
C10 C 0.0079(2) 0.59209(10) 0.55053(14) 0.0531(6) Uani 1 1 d . . . . .
C11 C 0.0902(2) 0.58423(9) 0.61358(13) 0.0512(6) Uani 1 1 d . . . . .
C12 C 0.1051(2) 0.54344(10) 0.64485(14) 0.0543(6) Uani 1 1 d . . . . .
H12 H 0.0608 0.5195 0.6251 0.065 Uiso 1 1 calc R U . . .
C13 C 0.1872(2) 0.53779(9) 0.70660(13) 0.0495(6) Uani 1 1 d . . . . .
C14 C 0.2031(2) 0.49720(9) 0.74420(13) 0.0497(6) Uani 1 1 d . . . . .
C15 C 0.1441(2) 0.45744(9) 0.73352(14) 0.0545(6) Uani 1 1 d . . . . .
H15 H 0.0778 0.4519 0.6998 0.065 Uiso 1 1 calc R U . . .
C16 C 0.2006(3) 0.42724(10) 0.78160(15) 0.0553(6) Uani 1 1 d . . . . .
H16 H 0.1794 0.3975 0.7863 0.066 Uiso 1 1 calc R U . . .
C17 C 0.2944(2) 0.44872(9) 0.82182(13) 0.0497(6) Uani 1 1 d . . . . .
C18 C 0.3827(2) 0.43021(9) 0.87647(13) 0.0494(6) Uani 1 1 d . . . . .
C19 C 0.4720(3) 0.45555(10) 0.91296(14) 0.0540(6) Uani 1 1 d . . . . .
H19 H 0.4772 0.4856 0.9021 0.065 Uiso 1 1 calc R U . . .
C20 C 0.5537(3) 0.43677(10) 0.96532(15) 0.0612(7) Uani 1 1 d . . . . .
H20 H 0.6137 0.4542 0.9898 0.073 Uiso 1 1 calc R U . . .
C21 C 0.5467(3) 0.39280(10) 0.98128(15) 0.0631(7) Uani 1 1 d . . . . .
H21 H 0.6011 0.3802 1.0174 0.076 Uiso 1 1 calc R U . . .
C22 C 0.4604(3) 0.36715(11) 0.94446(15) 0.0632(7) Uani 1 1 d . . . . .
H22 H 0.4573 0.3369 0.9545 0.076 Uiso 1 1 calc R U . . .
C23 C 0.3781(3) 0.38568(10) 0.89274(15) 0.0581(7) Uani 1 1 d . . . . .
H23 H 0.3186 0.3680 0.8684 0.070 Uiso 1 1 calc R U . . .
C24 C 0.3120(3) 0.65141(9) 0.73535(14) 0.0574(7) Uani 1 1 d . . . . .
C25 C 0.2712(3) 0.67253(10) 0.80043(15) 0.0672(8) Uani 1 1 d . . . . .
H25 H 0.1980 0.6640 0.8228 0.081 Uiso 1 1 calc R U . . .
C26 C 0.3417(3) 0.70657(11) 0.83132(17) 0.0717(9) Uani 1 1 d . . . . .
H26 H 0.3158 0.7209 0.8753 0.086 Uiso 1 1 calc R U . . .
C27 C 0.4478(3) 0.71951(11) 0.79891(17) 0.0710(9) Uani 1 1 d . . . . .
H27 H 0.4930 0.7428 0.8206 0.085 Uiso 1 1 calc R U . . .
C28 C 0.4900(3) 0.69879(10) 0.73435(16) 0.0640(8) Uani 1 1 d . . . . .
H28 H 0.5627 0.7075 0.7117 0.077 Uiso 1 1 calc R U . . .
C29 C 0.4191(3) 0.66442(9) 0.70483(14) 0.0551(7) Uani 1 1 d . . . . .
C30 C 0.4478(3) 0.63627(9) 0.63892(14) 0.0542(6) Uani 1 1 d . . . . .
N1 N 0.2937(2) 0.49123(7) 0.79902(11) 0.0495(5) Uani 1 1 d . . . . .
H1A H 0.3430 0.5115 0.8164 0.059 Uiso 1 1 calc R U . . .
N2 N -0.0003(2) 0.63193(8) 0.51408(11) 0.0539(5) Uani 1 1 d . . . . .
H2A H 0.0423 0.6552 0.5259 0.065 Uiso 1 1 calc R U . . .
O1 O 0.15008(17) 0.61883(6) 0.64051(10) 0.0574(5) Uani 1 1 d . . . . .
O2 O 0.25349(17) 0.57065(6) 0.73124(10) 0.0560(5) Uani 1 1 d . . . . .
B1 B 0.2630(3) 0.61095(11) 0.68650(16) 0.0530(7) Uani 1 1 d . . . . .
C32 C 1.0421(3) 0.32309(10) 0.96244(18) 0.0689(8) Uani 1 1 d . . . . .
H32 H 1.1039 0.3021 0.9704 0.083 Uiso 1 1 calc R U . . .
C33 C 0.9728(3) 0.33596(11) 1.02194(17) 0.0725(9) Uani 1 1 d . . . . .
H33 H 0.9860 0.3234 1.0703 0.087 Uiso 1 1 calc R U . . .
C34 C 0.8840(3) 0.36723(11) 1.01081(17) 0.0671(8) Uani 1 1 d . . . . .
H34 H 0.8372 0.3765 1.0517 0.081 Uiso 1 1 calc R U . . .
C35 C 0.8633(3) 0.38522(10) 0.93936(15) 0.0605(7) Uani 1 1 d . . . . .
H35 H 0.8023 0.4066 0.9322 0.073 Uiso 1 1 calc R U . . .
C50 C 0.3641(3) 0.66817(11) 0.38290(18) 0.0747(9) Uani 1 1 d . . . . .
H50 H 0.3255 0.6901 0.4110 0.090 Uiso 1 1 calc R U . . .
C51 C 0.3611(3) 0.66986(12) 0.3037(2) 0.0755(10) Uani 1 1 d . . . . .
H51 H 0.3211 0.6930 0.2779 0.091 Uiso 1 1 calc R U . . .
C52 C 0.4168(3) 0.63760(13) 0.26420(17) 0.0754(10) Uani 1 1 d . . . . .
H52 H 0.4146 0.6385 0.2108 0.091 Uiso 1 1 calc R U . . .
C53 C 0.4765(3) 0.60355(12) 0.30092(15) 0.0688(9) Uani 1 1 d . . . . .
H53 H 0.5134 0.5815 0.2723 0.083 Uiso 1 1 calc R U . . .
B2 B 0.6837(3) 0.54240(10) 0.71821(15) 0.0516(7) Uani 1 1 d . . . . .
O3 O 0.36297(18) 0.60540(6) 0.63044(10) 0.0570(5) Uani 1 1 d . . . . .
O4 O 0.53392(19) 0.63964(7) 0.59779(10) 0.0618(5) Uani 1 1 d . . . . .
C31 C 1.0221(3) 0.34062(10) 0.89081(17) 0.0610(7) Uani 1 1 d . . . . .
H31 H 1.0698 0.3313 0.8504 0.073 Uiso 1 1 calc R U . . .
C36 C 0.9318(3) 0.37203(9) 0.87815(15) 0.0546(6) Uani 1 1 d . . . . .
C37 C 0.9066(2) 0.38904(9) 0.80165(14) 0.0515(6) Uani 1 1 d . . . . .
C38 C 0.9230(2) 0.36940(9) 0.73171(14) 0.0538(6) Uani 1 1 d . . . . .
H38 H 0.9590 0.3419 0.7235 0.065 Uiso 1 1 calc R U . . .
C39 C 0.8770(2) 0.39747(9) 0.67587(15) 0.0521(6) Uani 1 1 d . . . . .
H39 H 0.8755 0.3923 0.6232 0.063 Uiso 1 1 calc R U . . .
C40 C 0.8335(2) 0.43451(9) 0.71164(13) 0.0478(6) Uani 1 1 d . . . . .
C41 C 0.7766(2) 0.47319(9) 0.68278(13) 0.0496(6) Uani 1 1 d . . . . .
C42 C 0.7368(2) 0.47862(9) 0.60831(13) 0.0492(6) Uani 1 1 d . . . . .
H42 H 0.7493 0.4564 0.5725 0.059 Uiso 1 1 calc R U . . .
C43 C 0.6787(2) 0.51691(9) 0.58681(13) 0.0473(6) Uani 1 1 d . . . . .
C44 C 0.6350(2) 0.52629(9) 0.51145(13) 0.0480(6) Uani 1 1 d . . . . .
C45 C 0.6393(2) 0.50103(9) 0.44584(13) 0.0515(6) Uani 1 1 d . . . . .
H45 H 0.6729 0.4728 0.4415 0.062 Uiso 1 1 calc R U . . .
C46 C 0.5843(2) 0.52563(10) 0.38780(13) 0.0543(7) Uani 1 1 d . . . . .
H46 H 0.5743 0.5168 0.3368 0.065 Uiso 1 1 calc R U . . .
C47 C 0.5468(2) 0.56508(9) 0.41733(13) 0.0516(6) Uani 1 1 d . . . . .
C48 C 0.4827(2) 0.60145(10) 0.38030(14) 0.0544(7) Uani 1 1 d . . . . .
C49 C 0.4240(3) 0.63419(10) 0.41970(16) 0.0645(8) Uani 1 1 d . . . . .
H49 H 0.4250 0.6332 0.4731 0.077 Uiso 1 1 calc R U . . .
C54 C 0.7291(2) 0.58619(9) 0.75926(13) 0.0496(6) Uani 1 1 d . . . . .
C55 C 0.8286(3) 0.61363(9) 0.75282(14) 0.0552(6) Uani 1 1 d . . . . .
H55 H 0.8893 0.6073 0.7178 0.066 Uiso 1 1 calc R U . . .
C56 C 0.8383(3) 0.65062(9) 0.79844(15) 0.0577(7) Uani 1 1 d . . . . .
H56 H 0.9055 0.6695 0.7940 0.069 Uiso 1 1 calc R U . . .
C57 C 0.7493(3) 0.65997(10) 0.85067(14) 0.0588(7) Uani 1 1 d . . . . .
H57 H 0.7574 0.6850 0.8815 0.071 Uiso 1 1 calc R U . . .
C58 C 0.6496(3) 0.63313(9) 0.85784(13) 0.0543(6) Uani 1 1 d . . . . .
H58 H 0.5890 0.6395 0.8930 0.065 Uiso 1 1 calc R U . . .
C59 C 0.6411(2) 0.59646(8) 0.81176(12) 0.0487(6) Uani 1 1 d . . . . .
C60 C 0.5434(3) 0.56327(9) 0.80903(12) 0.0503(6) Uani 1 1 d . . . . .
O5 O 0.76384(17) 0.50450(6) 0.73351(9) 0.0558(5) Uani 1 1 d . . . . .
O6 O 0.66003(17) 0.54860(6) 0.63589(9) 0.0522(4) Uani 1 1 d . . . . .
O7 O 0.56477(17) 0.53349(6) 0.75516(9) 0.0524(4) Uani 1 1 d . . . . .
O8 O 0.45467(18) 0.56101(6) 0.84879(9) 0.0568(5) Uani 1 1 d . . . . .
N3 N 0.57807(19) 0.56484(7) 0.49305(10) 0.0495(5) Uani 1 1 d . . . . .
H3A H 0.5638 0.5860 0.5247 0.059 Uiso 1 1 calc R U . . .
N4 N 0.8529(2) 0.42858(7) 0.78849(12) 0.0512(5) Uani 1 1 d . . . . .
H4A H 0.8336 0.4473 0.8234 0.061 Uiso 1 1 calc R U . . .
C61 C 0.9967(3) 0.52995(12) 0.88472(18) 0.0745(9) Uani 1 1 d . . . . .
H61 H 1.0181 0.5036 0.8574 0.112 Uiso 1 1 calc R U . . .
H61A H 1.0606 0.5367 0.9222 0.112 Uiso 1 1 calc R U . . .
H61B H 0.9878 0.5541 0.8493 0.112 Uiso 1 1 calc R U . . .
C62 C 0.8803(3) 0.52301(10) 0.92324(14) 0.0568(7) Uani 1 1 d . . . . .
C63 C 0.8405(3) 0.55765(11) 0.97657(18) 0.0710(8) Uani 1 1 d . . . . .
H63 H 0.7593 0.5509 0.9937 0.107 Uiso 1 1 calc R U . . .
H63A H 0.8394 0.5857 0.9508 0.107 Uiso 1 1 calc R U . . .
H63B H 0.8969 0.5589 1.0200 0.107 Uiso 1 1 calc R U . . .
O9 O 0.8199(2) 0.49029(7) 0.91250(11) 0.0681(5) Uani 1 1 d . . . . .
C64 C 0.7783(3) 0.70232(12) 0.59069(18) 0.0741(9) Uani 1 1 d . . . . .
H64 H 0.8007 0.7044 0.6443 0.111 Uiso 1 1 calc R U . . .
H64A H 0.8508 0.7053 0.5608 0.111 Uiso 1 1 calc R U . . .
H64B H 0.7407 0.6741 0.5805 0.111 Uiso 1 1 calc R U . . .
C65 C 0.6909(3) 0.73757(11) 0.57013(17) 0.0693(8) Uani 1 1 d . . . . .
C66 C 0.6292(3) 0.73442(12) 0.49367(17) 0.0777(9) Uani 1 1 d . . . . .
H66 H 0.5787 0.7601 0.4849 0.117 Uiso 1 1 calc R U . . .
H66A H 0.5786 0.7084 0.4914 0.117 Uiso 1 1 calc R U . . .
H66B H 0.6903 0.7327 0.4550 0.117 Uiso 1 1 calc R U . . .
O10 O 0.6689(3) 0.76718(9) 0.61333(14) 0.1019(9) Uani 1 1 d . . . . .
C67 C 0.2890(4) 0.76669(14) 0.5833(3) 0.1007(13) Uani 1 1 d . . . . .
H67 H 0.3291 0.7623 0.5354 0.151 Uiso 1 1 calc R U . . .
H67A H 0.3476 0.7625 0.6250 0.151 Uiso 1 1 calc R U . . .
H67B H 0.2564 0.7962 0.5851 0.151 Uiso 1 1 calc R U . . .
C68 C 0.1880(3) 0.73463(11) 0.58971(18) 0.0724(9) Uani 1 1 d . . . . .
C69 C 0.1177(4) 0.73530(14) 0.6603(2) 0.0946(12) Uani 1 1 d . . . . .
H69 H 0.0648 0.7608 0.6601 0.142 Uiso 1 1 calc R U . . .
H69A H 0.1736 0.7366 0.7039 0.142 Uiso 1 1 calc R U . . .
H69B H 0.0686 0.7089 0.6630 0.142 Uiso 1 1 calc R U . . .
O11 O 0.1639(2) 0.70935(8) 0.53866(12) 0.0779(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.391(4) . ?
C1 C2 1.401(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.404(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.427(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.476(4) . ?
C7 N2 1.388(3) . ?
C7 C8 1.397(4) . ?
C8 C9 1.406(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(4) . ?
C9 H9 0.9500 . ?
C10 N2 1.391(4) . ?
C10 C11 1.445(3) . ?
C11 O1 1.338(3) . ?
C11 C12 1.384(4) . ?
C12 C13 1.415(3) . ?
C12 H12 0.9500 . ?
C13 O2 1.319(3) . ?
C13 C14 1.428(4) . ?
C14 N1 1.391(3) . ?
C14 C15 1.400(4) . ?
C15 C16 1.400(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.409(4) . ?
C16 H16 0.9500 . ?
C17 N1 1.373(3) . ?
C17 C18 1.473(4) . ?
C18 C19 1.404(4) . ?
C18 C23 1.405(4) . ?
C19 C20 1.404(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.390(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.398(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C29 1.379(4) . ?
C24 C25 1.414(4) . ?
C24 B1 1.606(4) . ?
C25 C26 1.410(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.383(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.406(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.411(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.501(4) . ?
C30 O4 1.223(3) . ?
C30 O3 1.343(3) . ?
N1 H1A 0.8800 . ?
N2 H2A 0.8800 . ?
O1 B1 1.494(3) . ?
O2 B1 1.482(4) . ?
B1 O3 1.521(4) . ?
C32 C33 1.383(5) . ?
C32 C31 1.396(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.387(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.400(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.406(4) . ?
C35 H35 0.9500 . ?
C50 C49 1.393(4) . ?
C50 C51 1.410(5) . ?
C50 H50 0.9500 . ?
C51 C52 1.375(5) . ?
C51 H51 0.9500 . ?
C52 C53 1.393(5) . ?
C52 H52 0.9500 . ?
C53 C48 1.414(4) . ?
C53 H53 0.9500 . ?
B2 O5 1.487(4) . ?
B2 O6 1.493(3) . ?
B2 O7 1.514(4) . ?
B2 C54 1.609(4) . ?
C31 C36 1.405(4) . ?
C31 H31 0.9500 . ?
C36 C37 1.478(4) . ?
C37 N4 1.374(3) . ?
C37 C38 1.401(4) . ?
C38 C39 1.402(4) . ?
C38 H38 0.9500 . ?
C39 C40 1.400(4) . ?
C39 H39 0.9500 . ?
C40 N4 1.390(3) . ?
C40 C41 1.437(4) . ?
C41 O5 1.333(3) . ?
C41 C42 1.394(3) . ?
C42 C43 1.393(4) . ?
C42 H42 0.9500 . ?
C43 O6 1.331(3) . ?
C43 C44 1.441(3) . ?
C44 N3 1.381(3) . ?
C44 C45 1.406(3) . ?
C45 C46 1.406(4) . ?
C45 H45 0.9500 . ?
C46 C47 1.393(4) . ?
C46 H46 0.9500 . ?
C47 N3 1.381(3) . ?
C47 C48 1.473(4) . ?
C48 C49 1.401(4) . ?
C49 H49 0.9500 . ?
C54 C55 1.397(4) . ?
C54 C59 1.406(4) . ?
C55 C56 1.403(4) . ?
C55 H55 0.9500 . ?
C56 C57 1.404(4) . ?
C56 H56 0.9500 . ?
C57 C58 1.388(4) . ?
C57 H57 0.9500 . ?
C58 C59 1.399(4) . ?
C58 H58 0.9500 . ?
C59 C60 1.489(4) . ?
C60 O8 1.229(3) . ?
C60 O7 1.354(3) . ?
N3 H3A 0.8800 . ?
N4 H4A 0.8800 . ?
C61 C62 1.493(4) . ?
C61 H61 0.9800 . ?
C61 H61A 0.9800 . ?
C61 H61B 0.9800 . ?
C62 O9 1.222(3) . ?
C62 C63 1.504(4) . ?
C63 H63 0.9800 . ?
C63 H63A 0.9800 . ?
C63 H63B 0.9800 . ?
C64 C65 1.493(5) . ?
C64 H64 0.9800 . ?
C64 H64A 0.9800 . ?
C64 H64B 0.9800 . ?
C65 O10 1.223(4) . ?
C65 C66 1.508(4) . ?
C66 H66 0.9800 . ?
C66 H66A 0.9800 . ?
C66 H66B 0.9800 . ?
C67 C68 1.499(5) . ?
C67 H67 0.9800 . ?
C67 H67A 0.9800 . ?
C67 H67B 0.9800 . ?
C68 O11 1.221(4) . ?
C68 C69 1.497(5) . ?
C69 H69 0.9800 . ?
C69 H69A 0.9800 . ?
C69 H69B 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.8(3) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.5(3) . . ?
C1 C6 C7 123.4(2) . . ?
C5 C6 C7 118.0(3) . . ?
N2 C7 C8 107.6(2) . . ?
N2 C7 C6 123.2(3) . . ?
C8 C7 C6 129.1(2) . . ?
C7 C8 C9 108.0(2) . . ?
C7 C8 H8 126.0 . . ?
C9 C8 H8 126.0 . . ?
C10 C9 C8 107.7(3) . . ?
C10 C9 H9 126.2 . . ?
C8 C9 H9 126.2 . . ?
N2 C10 C9 107.9(2) . . ?
N2 C10 C11 122.7(2) . . ?
C9 C10 C11 129.4(3) . . ?
O1 C11 C12 121.9(2) . . ?
O1 C11 C10 116.0(2) . . ?
C12 C11 C10 122.0(3) . . ?
C11 C12 C13 119.4(3) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
O2 C13 C12 120.1(2) . . ?
O2 C13 C14 117.3(2) . . ?
C12 C13 C14 122.6(2) . . ?
N1 C14 C15 107.6(2) . . ?
N1 C14 C13 121.4(2) . . ?
C15 C14 C13 130.9(2) . . ?
C16 C15 C14 107.6(2) . . ?
C16 C15 H15 126.2 . . ?
C14 C15 H15 126.2 . . ?
C15 C16 C17 107.9(3) . . ?
C15 C16 H16 126.1 . . ?
C17 C16 H16 126.1 . . ?
N1 C17 C16 107.5(2) . . ?
N1 C17 C18 124.3(2) . . ?
C16 C17 C18 128.1(3) . . ?
C19 C18 C23 118.6(2) . . ?
C19 C18 C17 122.3(2) . . ?
C23 C18 C17 119.2(2) . . ?
C18 C19 C20 120.5(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C21 C20 C19 120.0(3) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 120.1(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C23 120.2(3) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C18 120.6(3) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
C29 C24 C25 119.2(3) . . ?
C29 C24 B1 107.1(2) . . ?
C25 C24 B1 133.7(3) . . ?
C26 C25 C24 118.4(3) . . ?
C26 C25 H25 120.8 . . ?
C24 C25 H25 120.8 . . ?
C27 C26 C25 121.3(3) . . ?
C27 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?
C26 C27 C28 121.1(3) . . ?
C26 C27 H27 119.5 . . ?
C28 C27 H27 119.5 . . ?
C27 C28 C29 116.9(3) . . ?
C27 C28 H28 121.6 . . ?
C29 C28 H28 121.6 . . ?
C24 C29 C28 123.2(3) . . ?
C24 C29 C30 110.1(2) . . ?
C28 C29 C30 126.7(3) . . ?
O4 C30 O3 123.2(3) . . ?
O4 C30 C29 127.2(3) . . ?
O3 C30 C29 109.6(2) . . ?
C17 N1 C14 109.4(2) . . ?
C17 N1 H1A 125.3 . . ?
C14 N1 H1A 125.3 . . ?
C7 N2 C10 108.8(2) . . ?
C7 N2 H2A 125.6 . . ?
C10 N2 H2A 125.6 . . ?
C11 O1 B1 117.7(2) . . ?
C13 O2 B1 120.9(2) . . ?
O2 B1 O1 111.1(2) . . ?
O2 B1 O3 108.8(2) . . ?
O1 B1 O3 105.8(2) . . ?
O2 B1 C24 112.9(2) . . ?
O1 B1 C24 115.7(2) . . ?
O3 B1 C24 101.7(2) . . ?
C33 C32 C31 120.7(3) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C32 C33 C34 119.8(3) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
C33 C34 C35 120.1(3) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 H34 119.9 . . ?
C34 C35 C36 120.8(3) . . ?
C34 C35 H35 119.6 . . ?
C36 C35 H35 119.6 . . ?
C49 C50 C51 119.6(3) . . ?
C49 C50 H50 120.2 . . ?
C51 C50 H50 120.2 . . ?
C52 C51 C50 119.1(3) . . ?
C52 C51 H51 120.4 . . ?
C50 C51 H51 120.4 . . ?
C51 C52 C53 121.3(3) . . ?
C51 C52 H52 119.3 . . ?
C53 C52 H52 119.3 . . ?
C52 C53 C48 120.8(3) . . ?
C52 C53 H53 119.6 . . ?
C48 C53 H53 119.6 . . ?
O5 B2 O6 111.5(2) . . ?
O5 B2 O7 107.4(2) . . ?
O6 B2 O7 108.6(2) . . ?
O5 B2 C54 113.6(2) . . ?
O6 B2 C54 112.4(2) . . ?
O7 B2 C54 102.6(2) . . ?
C30 O3 B1 111.5(2) . . ?
C32 C31 C36 120.4(3) . . ?
C32 C31 H31 119.8 . . ?
C36 C31 H31 119.8 . . ?
C31 C36 C35 118.2(3) . . ?
C31 C36 C37 120.5(3) . . ?
C35 C36 C37 121.3(3) . . ?
N4 C37 C38 107.4(2) . . ?
N4 C37 C36 122.8(2) . . ?
C38 C37 C36 129.7(3) . . ?
C37 C38 C39 108.0(2) . . ?
C37 C38 H38 126.0 . . ?
C39 C38 H38 126.0 . . ?
C40 C39 C38 107.7(2) . . ?
C40 C39 H39 126.1 . . ?
C38 C39 H39 126.1 . . ?
N4 C40 C39 107.1(2) . . ?
N4 C40 C41 120.9(2) . . ?
C39 C40 C41 131.9(2) . . ?
O5 C41 C42 121.3(2) . . ?
O5 C41 C40 114.4(2) . . ?
C42 C41 C40 124.2(2) . . ?
C41 C42 C43 119.5(2) . . ?
C41 C42 H42 120.2 . . ?
C43 C42 H42 120.2 . . ?
O6 C43 C42 121.5(2) . . ?
O6 C43 C44 114.1(2) . . ?
C42 C43 C44 124.4(2) . . ?
N3 C44 C45 107.9(2) . . ?
N3 C44 C43 122.1(2) . . ?
C45 C44 C43 130.0(3) . . ?
C44 C45 C46 106.7(2) . . ?
C44 C45 H45 126.7 . . ?
C46 C45 H45 126.7 . . ?
C47 C46 C45 108.8(2) . . ?
C47 C46 H46 125.6 . . ?
C45 C46 H46 125.6 . . ?
N3 C47 C46 107.1(2) . . ?
N3 C47 C48 123.0(2) . . ?
C46 C47 C48 129.9(2) . . ?
C49 C48 C53 117.2(3) . . ?
C49 C48 C47 123.4(2) . . ?
C53 C48 C47 119.4(3) . . ?
C50 C49 C48 121.9(3) . . ?
C50 C49 H49 119.0 . . ?
C48 C49 H49 119.0 . . ?
C55 C54 C59 118.8(2) . . ?
C55 C54 B2 135.1(2) . . ?
C59 C54 B2 106.1(2) . . ?
C54 C55 C56 119.5(3) . . ?
C54 C55 H55 120.2 . . ?
C56 C55 H55 120.2 . . ?
C55 C56 C57 120.5(3) . . ?
C55 C56 H56 119.8 . . ?
C57 C56 H56 119.8 . . ?
C58 C57 C56 120.9(3) . . ?
C58 C57 H57 119.6 . . ?
C56 C57 H57 119.5 . . ?
C57 C58 C59 117.9(3) . . ?
C57 C58 H58 121.0 . . ?
C59 C58 H58 121.0 . . ?
C58 C59 C54 122.4(3) . . ?
C58 C59 C60 127.7(2) . . ?
C54 C59 C60 109.9(2) . . ?
O8 C60 O7 121.9(2) . . ?
O8 C60 C59 127.7(2) . . ?
O7 C60 C59 110.3(2) . . ?
C41 O5 B2 121.35(19) . . ?
C43 O6 B2 121.6(2) . . ?
C60 O7 B2 110.9(2) . . ?
C47 N3 C44 109.6(2) . . ?
C47 N3 H3A 125.2 . . ?
C44 N3 H3A 125.2 . . ?
C37 N4 C40 109.8(2) . . ?
C37 N4 H4A 125.1 . . ?
C40 N4 H4A 125.1 . . ?
C62 C61 H61 109.5 . . ?
C62 C61 H61A 109.5 . . ?
H61 C61 H61A 109.5 . . ?
C62 C61 H61B 109.5 . . ?
H61 C61 H61B 109.5 . . ?
H61A C61 H61B 109.5 . . ?
O9 C62 C61 121.4(3) . . ?
O9 C62 C63 121.1(3) . . ?
C61 C62 C63 117.4(3) . . ?
C62 C63 H63 109.5 . . ?
C62 C63 H63A 109.5 . . ?
H63 C63 H63A 109.5 . . ?
C62 C63 H63B 109.5 . . ?
H63 C63 H63B 109.5 . . ?
H63A C63 H63B 109.5 . . ?
C65 C64 H64 109.5 . . ?
C65 C64 H64A 109.5 . . ?
H64 C64 H64A 109.5 . . ?
C65 C64 H64B 109.5 . . ?
H64 C64 H64B 109.5 . . ?
H64A C64 H64B 109.5 . . ?
O10 C65 C64 122.0(3) . . ?
O10 C65 C66 121.5(3) . . ?
C64 C65 C66 116.6(3) . . ?
C65 C66 H66 109.5 . . ?
C65 C66 H66A 109.5 . . ?
H66 C66 H66A 109.5 . . ?
C65 C66 H66B 109.5 . . ?
H66 C66 H66B 109.5 . . ?
H66A C66 H66B 109.5 . . ?
C68 C67 H67 109.5 . . ?
C68 C67 H67A 109.5 . . ?
H67 C67 H67A 109.5 . . ?
C68 C67 H67B 109.5 . . ?
H67 C67 H67B 109.5 . . ?
H67A C67 H67B 109.5 . . ?
O11 C68 C69 121.7(4) . . ?
O11 C68 C67 120.8(4) . . ?
C69 C68 C67 117.5(3) . . ?
C68 C69 H69 109.5 . . ?
C68 C69 H69A 109.5 . . ?
H69 C69 H69A 109.5 . . ?
C68 C69 H69B 109.5 . . ?
H69 C69 H69B 109.5 . . ?
H69A C69 H69B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.7(5) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C2 C1 C6 C5 -1.6(4) . . . . ?
C2 C1 C6 C7 175.6(3) . . . . ?
C4 C5 C6 C1 1.5(4) . . . . ?
C4 C5 C6 C7 -175.8(3) . . . . ?
C1 C6 C7 N2 12.1(4) . . . . ?
C5 C6 C7 N2 -170.8(3) . . . . ?
C1 C6 C7 C8 -164.3(3) . . . . ?
C5 C6 C7 C8 12.9(4) . . . . ?
N2 C7 C8 C9 0.0(3) . . . . ?
C6 C7 C8 C9 176.8(3) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C8 C9 C10 N2 -1.0(3) . . . . ?
C8 C9 C10 C11 -179.5(3) . . . . ?
N2 C10 C11 O1 6.7(4) . . . . ?
C9 C10 C11 O1 -174.9(3) . . . . ?
N2 C10 C11 C12 -174.0(2) . . . . ?
C9 C10 C11 C12 4.4(5) . . . . ?
O1 C11 C12 C13 -0.8(4) . . . . ?
C10 C11 C12 C13 180.0(2) . . . . ?
C11 C12 C13 O2 -3.8(4) . . . . ?
C11 C12 C13 C14 176.8(2) . . . . ?
O2 C13 C14 N1 -6.9(4) . . . . ?
C12 C13 C14 N1 172.6(2) . . . . ?
O2 C13 C14 C15 177.3(3) . . . . ?
C12 C13 C14 C15 -3.3(4) . . . . ?
N1 C14 C15 C16 -0.7(3) . . . . ?
C13 C14 C15 C16 175.6(3) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 N1 0.6(3) . . . . ?
C15 C16 C17 C18 -177.0(2) . . . . ?
N1 C17 C18 C19 2.9(4) . . . . ?
C16 C17 C18 C19 -179.8(3) . . . . ?
N1 C17 C18 C23 -176.9(2) . . . . ?
C16 C17 C18 C23 0.4(4) . . . . ?
C23 C18 C19 C20 -0.9(4) . . . . ?
C17 C18 C19 C20 179.3(3) . . . . ?
C18 C19 C20 C21 0.1(4) . . . . ?
C19 C20 C21 C22 1.2(4) . . . . ?
C20 C21 C22 C23 -1.7(5) . . . . ?
C21 C22 C23 C18 1.0(4) . . . . ?
C19 C18 C23 C22 0.3(4) . . . . ?
C17 C18 C23 C22 -179.8(3) . . . . ?
C29 C24 C25 C26 0.6(4) . . . . ?
B1 C24 C25 C26 176.6(3) . . . . ?
C24 C25 C26 C27 0.5(5) . . . . ?
C25 C26 C27 C28 -0.8(5) . . . . ?
C26 C27 C28 C29 -0.1(4) . . . . ?
C25 C24 C29 C28 -1.5(4) . . . . ?
B1 C24 C29 C28 -178.6(2) . . . . ?
C25 C24 C29 C30 177.1(2) . . . . ?
B1 C24 C29 C30 0.1(3) . . . . ?
C27 C28 C29 C24 1.3(4) . . . . ?
C27 C28 C29 C30 -177.1(3) . . . . ?
C24 C29 C30 O4 177.7(3) . . . . ?
C28 C29 C30 O4 -3.7(4) . . . . ?
C24 C29 C30 O3 -2.4(3) . . . . ?
C28 C29 C30 O3 176.2(2) . . . . ?
C16 C17 N1 C14 -1.1(3) . . . . ?
C18 C17 N1 C14 176.7(2) . . . . ?
C15 C14 N1 C17 1.1(3) . . . . ?
C13 C14 N1 C17 -175.6(2) . . . . ?
C8 C7 N2 C10 -0.6(3) . . . . ?
C6 C7 N2 C10 -177.6(2) . . . . ?
C9 C10 N2 C7 1.0(3) . . . . ?
C11 C10 N2 C7 179.7(2) . . . . ?
C12 C11 O1 B1 20.8(4) . . . . ?
C10 C11 O1 B1 -159.9(2) . . . . ?
C12 C13 O2 B1 -12.7(4) . . . . ?
C14 C13 O2 B1 166.7(2) . . . . ?
C13 O2 B1 O1 30.4(3) . . . . ?
C13 O2 B1 O3 -85.6(3) . . . . ?
C13 O2 B1 C24 162.3(2) . . . . ?
C11 O1 B1 O2 -33.9(3) . . . . ?
C11 O1 B1 O3 84.0(3) . . . . ?
C11 O1 B1 C24 -164.3(2) . . . . ?
C29 C24 B1 O2 118.3(3) . . . . ?
C25 C24 B1 O2 -58.1(4) . . . . ?
C29 C24 B1 O1 -112.2(3) . . . . ?
C25 C24 B1 O1 71.4(4) . . . . ?
C29 C24 B1 O3 1.9(3) . . . . ?
C25 C24 B1 O3 -174.6(3) . . . . ?
C31 C32 C33 C34 -1.2(5) . . . . ?
C32 C33 C34 C35 1.0(5) . . . . ?
C33 C34 C35 C36 -0.1(5) . . . . ?
C49 C50 C51 C52 0.5(5) . . . . ?
C50 C51 C52 C53 -0.4(5) . . . . ?
C51 C52 C53 C48 -0.8(5) . . . . ?
O4 C30 O3 B1 -176.4(2) . . . . ?
C29 C30 O3 B1 3.7(3) . . . . ?
O2 B1 O3 C30 -122.8(2) . . . . ?
O1 B1 O3 C30 117.8(2) . . . . ?
C24 B1 O3 C30 -3.4(3) . . . . ?
C33 C32 C31 C36 0.6(5) . . . . ?
C32 C31 C36 C35 0.2(4) . . . . ?
C32 C31 C36 C37 -177.0(3) . . . . ?
C34 C35 C36 C31 -0.5(4) . . . . ?
C34 C35 C36 C37 176.7(3) . . . . ?
C31 C36 C37 N4 -157.0(3) . . . . ?
C35 C36 C37 N4 25.8(4) . . . . ?
C31 C36 C37 C38 27.2(4) . . . . ?
C35 C36 C37 C38 -149.9(3) . . . . ?
N4 C37 C38 C39 -0.7(3) . . . . ?
C36 C37 C38 C39 175.6(3) . . . . ?
C37 C38 C39 C40 0.6(3) . . . . ?
C38 C39 C40 N4 -0.3(3) . . . . ?
C38 C39 C40 C41 -179.4(3) . . . . ?
N4 C40 C41 O5 10.6(4) . . . . ?
C39 C40 C41 O5 -170.4(3) . . . . ?
N4 C40 C41 C42 -169.3(2) . . . . ?
C39 C40 C41 C42 9.7(5) . . . . ?
O5 C41 C42 C43 -2.3(4) . . . . ?
C40 C41 C42 C43 177.7(2) . . . . ?
C41 C42 C43 O6 -0.1(4) . . . . ?
C41 C42 C43 C44 179.3(2) . . . . ?
O6 C43 C44 N3 -0.5(3) . . . . ?
C42 C43 C44 N3 -179.9(2) . . . . ?
O6 C43 C44 C45 179.7(3) . . . . ?
C42 C43 C44 C45 0.3(4) . . . . ?
N3 C44 C45 C46 0.4(3) . . . . ?
C43 C44 C45 C46 -179.7(3) . . . . ?
C44 C45 C46 C47 -0.1(3) . . . . ?
C45 C46 C47 N3 -0.2(3) . . . . ?
C45 C46 C47 C48 -178.5(3) . . . . ?
C52 C53 C48 C49 1.7(4) . . . . ?
C52 C53 C48 C47 -179.8(3) . . . . ?
N3 C47 C48 C49 -14.9(4) . . . . ?
C46 C47 C48 C49 163.2(3) . . . . ?
N3 C47 C48 C53 166.7(2) . . . . ?
C46 C47 C48 C53 -15.2(4) . . . . ?
C51 C50 C49 C48 0.5(5) . . . . ?
C53 C48 C49 C50 -1.5(4) . . . . ?
C47 C48 C49 C50 180.0(3) . . . . ?
O5 B2 C54 C55 66.4(4) . . . . ?
O6 B2 C54 C55 -61.5(4) . . . . ?
O7 B2 C54 C55 -178.0(3) . . . . ?
O5 B2 C54 C59 -114.5(2) . . . . ?
O6 B2 C54 C59 117.6(2) . . . . ?
O7 B2 C54 C59 1.1(3) . . . . ?
C59 C54 C55 C56 -0.2(4) . . . . ?
B2 C54 C55 C56 178.9(3) . . . . ?
C54 C55 C56 C57 0.5(4) . . . . ?
C55 C56 C57 C58 -0.6(4) . . . . ?
C56 C57 C58 C59 0.3(4) . . . . ?
C57 C58 C59 C54 0.0(4) . . . . ?
C57 C58 C59 C60 -179.8(2) . . . . ?
C55 C54 C59 C58 -0.1(4) . . . . ?
B2 C54 C59 C58 -179.4(2) . . . . ?
C55 C54 C59 C60 179.7(2) . . . . ?
B2 C54 C59 C60 0.4(3) . . . . ?
C58 C59 C60 O8 -3.2(4) . . . . ?
C54 C59 C60 O8 177.1(2) . . . . ?
C58 C59 C60 O7 177.7(2) . . . . ?
C54 C59 C60 O7 -2.1(3) . . . . ?
C42 C41 O5 B2 13.6(4) . . . . ?
C40 C41 O5 B2 -166.3(2) . . . . ?
O6 B2 O5 C41 -20.6(3) . . . . ?
O7 B2 O5 C41 98.3(3) . . . . ?
C54 B2 O5 C41 -148.9(2) . . . . ?
C42 C43 O6 B2 -9.0(4) . . . . ?
C44 C43 O6 B2 171.5(2) . . . . ?
O5 B2 O6 C43 18.3(3) . . . . ?
O7 B2 O6 C43 -99.9(3) . . . . ?
C54 B2 O6 C43 147.2(2) . . . . ?
O8 C60 O7 B2 -176.3(2) . . . . ?
C59 C60 O7 B2 2.8(3) . . . . ?
O5 B2 O7 C60 117.6(2) . . . . ?
O6 B2 O7 C60 -121.7(2) . . . . ?
C54 B2 O7 C60 -2.5(2) . . . . ?
C46 C47 N3 C44 0.5(3) . . . . ?
C48 C47 N3 C44 178.9(2) . . . . ?
C45 C44 N3 C47 -0.6(3) . . . . ?
C43 C44 N3 C47 179.6(2) . . . . ?
C38 C37 N4 C40 0.6(3) . . . . ?
C36 C37 N4 C40 -176.1(2) . . . . ?
C39 C40 N4 C37 -0.2(3) . . . . ?
C41 C40 N4 C37 179.1(2) . . . . ?

_refine_diff_density_max         0.819
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.056



####################################################################### 
# 
# 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_ydkr_a
_database_code_depnum_ccdc_archive 'CCDC 2086724'
loop_
_audit_author_name
_audit_author_address
'Nobuhiro Yasuda'
;Japan Synchrotron Radiation Research Institute
Japan
;
_audit_update_record             
;
2021-05-29 deposited with the CCDC.	2021-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 B F N2 O4'
_chemical_formula_sum            'C18 H14 B F N2 O4'
_chemical_formula_weight         352.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0045 0.0022 '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 0.0022 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0231 0.0137 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0085 0.0044 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0146 0.0081 '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                   5.2370(10)
_cell_length_b                   8.7976(15)
_cell_length_c                   34.892(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.923(10)
_cell_angle_gamma                90
_cell_volume                     1606.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    11992
_cell_measurement_theta_min      1.332
_cell_measurement_theta_max      29.083

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.020
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    0.148
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.514
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'ABSCOR (T.Higashi, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.81088
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'synchrotron radiation SPring-8 BL40XU'
_diffrn_radiation_monochromator  'Si(111) Channel Cut'
_diffrn_measurement_device_type  'DECTRIS EIGER X 1M'
_diffrn_measurement_method       'Shutterless ω scans'
_diffrn_detector_area_resol_mean 13.33
_diffrn_reflns_number            11992
_diffrn_reflns_av_unetI/netI     0.2172
_diffrn_reflns_av_R_equivalents  0.2288
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.332
_diffrn_reflns_theta_max         29.083
_diffrn_reflns_theta_full        29.083
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2891
_reflns_number_gt                1164
_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       'Rapid Auto(Rigaku)'
_computing_cell_refinement       'Rapid Auto(Rigaku)'
_computing_data_reduction        'Rapid Auto(Rigaku)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0698P)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         2891
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2164
_refine_ls_R_factor_gt           0.0867
_refine_ls_wR_factor_ref         0.2270
_refine_ls_wR_factor_gt          0.1700
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_restrained_S_all      0.943
_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
C1 C 0.3462(12) 0.7268(7) 0.63420(15) 0.0310(16) Uani 1 1 d . . . . .
N1 N 0.1993(10) 0.7170(6) 0.60058(12) 0.0351(14) Uani 1 1 d . . . . .
H12 H 0.2058 0.6432 0.5836 0.042 Uiso 1 1 calc R U . . .
C2 C 0.0447(13) 0.8393(7) 0.59815(17) 0.0408(18) Uani 1 1 d . . . . .
H1 H -0.0770 0.8593 0.5780 0.049 Uiso 1 1 calc R U . . .
C3 C 0.0912(14) 0.9294(8) 0.62924(17) 0.0476(19) Uani 1 1 d . . . . .
H2 H 0.0074 1.0223 0.6346 0.057 Uiso 1 1 calc R U . . .
C4 C 0.2838(13) 0.8613(7) 0.65177(16) 0.0393(18) Uani 1 1 d . . . . .
H3 H 0.3582 0.9004 0.6749 0.047 Uiso 1 1 calc R U . . .
B1 B 0.6455(16) 0.3420(9) 0.63376(19) 0.038(2) Uani 1 1 d . . . . .
O1 O 0.4992(8) 0.4839(5) 0.62432(10) 0.0357(11) Uani 1 1 d . . . . .
C5 C 0.5201(12) 0.6095(7) 0.64474(15) 0.0323(16) Uani 1 1 d . . . . .
C6 C 0.6972(12) 0.6181(7) 0.67527(14) 0.0345(17) Uani 1 1 d . . . . .
H4 H 0.7004 0.7046 0.6916 0.041 Uiso 1 1 calc R U . . .
C7 C 0.8676(13) 0.5015(7) 0.68191(15) 0.0313(16) Uani 1 1 d . . . . .
O2 O 0.8655(8) 0.3779(5) 0.66052(10) 0.0383(12) Uani 1 1 d . . . . .
C8 C 1.0618(12) 0.5043(7) 0.71235(15) 0.0311(15) Uani 1 1 d . . . . .
C9 C 1.0904(13) 0.5962(7) 0.74409(16) 0.0383(17) Uani 1 1 d . . . . .
H5 H 0.9849 0.6799 0.7503 0.046 Uiso 1 1 calc R U . . .
C10 C 1.2994(14) 0.5448(7) 0.76513(15) 0.0407(18) Uani 1 1 d . . . . .
H6 H 1.3633 0.5869 0.7886 0.049 Uiso 1 1 calc R U . . .
C11 C 1.4004(12) 0.4223(7) 0.74653(15) 0.0344(16) Uani 1 1 d . . . . .
H7 H 1.5463 0.3650 0.7546 0.041 Uiso 1 1 calc R U . . .
N2 N 1.2520(10) 0.3988(6) 0.71442(12) 0.0321(13) Uani 1 1 d . . . . .
H13 H 1.2753 0.3263 0.6975 0.039 Uiso 1 1 calc R U . . .
C12 C 0.7414(13) 0.2714(7) 0.59416(16) 0.0347(16) Uani 1 1 d . . . . .
C13 C 0.6257(13) 0.1491(7) 0.57567(15) 0.0372(17) Uani 1 1 d . . . . .
H8 H 0.4902 0.0970 0.5875 0.045 Uiso 1 1 calc R U . . .
C14 C 0.7064(14) 0.1016(7) 0.53977(15) 0.0377(17) Uani 1 1 d . . . . .
H9 H 0.6283 0.0158 0.5277 0.045 Uiso 1 1 calc R U . . .
C15 C 0.8973(13) 0.1777(7) 0.52180(16) 0.0357(16) Uani 1 1 d . . . . .
H10 H 0.9484 0.1454 0.4972 0.043 Uiso 1 1 calc R U . . .
C16 C 1.0157(13) 0.3014(7) 0.53933(16) 0.0347(16) Uani 1 1 d . . . . .
C17 C 0.9378(13) 0.3460(7) 0.57642(15) 0.0345(17) Uani 1 1 d . . . . .
H11 H 1.0220 0.4282 0.5892 0.041 Uiso 1 1 calc R U . . .
F1 F 0.4816(7) 0.2429(4) 0.65278(8) 0.0396(10) Uani 1 1 d . . . . .
O3 O 1.3092(8) 0.5057(5) 0.53542(10) 0.0410(12) Uani 1 1 d . . . . .
C18 C 1.2168(14) 0.3853(8) 0.52204(16) 0.0399(18) Uani 1 1 d . . . . .
O4 O 1.2963(9) 0.3337(5) 0.48837(11) 0.0428(12) Uani 1 1 d . . . . .
H14 H 1.4142 0.3897 0.4807 0.064 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
C1 C4 1.377(8) . ?
C1 N1 1.384(7) . ?
C1 C5 1.417(8) . ?
N1 C2 1.347(8) . ?
N1 H12 0.8800 . ?
C2 C3 1.359(8) . ?
C2 H1 0.9500 . ?
C3 C4 1.393(9) . ?
C3 H2 0.9500 . ?
C4 H3 0.9500 . ?
B1 F1 1.405(8) . ?
B1 O2 1.492(8) . ?
B1 O1 1.496(8) . ?
B1 C12 1.610(10) . ?
O1 C5 1.317(7) . ?
C5 C6 1.391(8) . ?
C6 C7 1.374(8) . ?
C6 H4 0.9500 . ?
C7 O2 1.319(6) . ?
C7 C8 1.446(8) . ?
C8 N2 1.362(7) . ?
C8 C9 1.375(8) . ?
C9 C10 1.374(9) . ?
C9 H5 0.9500 . ?
C10 C11 1.373(8) . ?
C10 H6 0.9500 . ?
C11 N2 1.358(7) . ?
C11 H7 0.9500 . ?
N2 H13 0.8800 . ?
C12 C17 1.383(9) . ?
C12 C13 1.384(8) . ?
C13 C14 1.399(8) . ?
C13 H8 0.9500 . ?
C14 C15 1.372(9) . ?
C14 H9 0.9500 . ?
C15 C16 1.385(8) . ?
C15 H10 0.9500 . ?
C16 C17 1.425(8) . ?
C16 C18 1.435(9) . ?
C17 H11 0.9500 . ?
O3 C18 1.249(7) . ?
C18 O4 1.339(7) . ?
O4 H14 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C1 N1 107.3(5) . . ?
C4 C1 C5 132.1(5) . . ?
N1 C1 C5 120.6(5) . . ?
C2 N1 C1 108.6(5) . . ?
C2 N1 H12 125.7 . . ?
C1 N1 H12 125.7 . . ?
N1 C2 C3 108.9(6) . . ?
N1 C2 H1 125.5 . . ?
C3 C2 H1 125.5 . . ?
C2 C3 C4 107.9(6) . . ?
C2 C3 H2 126.1 . . ?
C4 C3 H2 126.1 . . ?
C1 C4 C3 107.2(5) . . ?
C1 C4 H3 126.4 . . ?
C3 C4 H3 126.4 . . ?
F1 B1 O2 107.9(5) . . ?
F1 B1 O1 107.8(6) . . ?
O2 B1 O1 109.9(5) . . ?
F1 B1 C12 112.3(6) . . ?
O2 B1 C12 111.2(6) . . ?
O1 B1 C12 107.8(5) . . ?
C5 O1 B1 123.2(5) . . ?
O1 C5 C6 120.1(6) . . ?
O1 C5 C1 115.4(5) . . ?
C6 C5 C1 124.4(6) . . ?
C7 C6 C5 120.1(6) . . ?
C7 C6 H4 120.0 . . ?
C5 C6 H4 120.0 . . ?
O2 C7 C6 121.8(5) . . ?
O2 C7 C8 115.0(6) . . ?
C6 C7 C8 123.2(6) . . ?
C7 O2 B1 121.4(5) . . ?
N2 C8 C9 107.4(5) . . ?
N2 C8 C7 121.5(5) . . ?
C9 C8 C7 131.1(6) . . ?
C10 C9 C8 107.4(6) . . ?
C10 C9 H5 126.3 . . ?
C8 C9 H5 126.3 . . ?
C11 C10 C9 108.6(5) . . ?
C11 C10 H6 125.7 . . ?
C9 C10 H6 125.7 . . ?
N2 C11 C10 106.9(6) . . ?
N2 C11 H7 126.5 . . ?
C10 C11 H7 126.5 . . ?
C11 N2 C8 109.7(5) . . ?
C11 N2 H13 125.1 . . ?
C8 N2 H13 125.1 . . ?
C17 C12 C13 118.7(6) . . ?
C17 C12 B1 117.4(6) . . ?
C13 C12 B1 123.7(6) . . ?
C12 C13 C14 120.6(7) . . ?
C12 C13 H8 119.7 . . ?
C14 C13 H8 119.7 . . ?
C15 C14 C13 120.7(6) . . ?
C15 C14 H9 119.7 . . ?
C13 C14 H9 119.7 . . ?
C14 C15 C16 120.3(6) . . ?
C14 C15 H10 119.9 . . ?
C16 C15 H10 119.9 . . ?
C15 C16 C17 118.7(6) . . ?
C15 C16 C18 122.8(6) . . ?
C17 C16 C18 118.5(6) . . ?
C12 C17 C16 121.1(6) . . ?
C12 C17 H11 119.5 . . ?
C16 C17 H11 119.5 . . ?
O3 C18 O4 119.2(7) . . ?
O3 C18 C16 124.0(6) . . ?
O4 C18 C16 116.7(6) . . ?
C18 O4 H14 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C1 N1 C2 -2.0(7) . . . . ?
C5 C1 N1 C2 177.7(6) . . . . ?
C1 N1 C2 C3 0.9(7) . . . . ?
N1 C2 C3 C4 0.5(8) . . . . ?
N1 C1 C4 C3 2.3(7) . . . . ?
C5 C1 C4 C3 -177.4(7) . . . . ?
C2 C3 C4 C1 -1.7(8) . . . . ?
F1 B1 O1 C5 100.0(6) . . . . ?
O2 B1 O1 C5 -17.3(8) . . . . ?
C12 B1 O1 C5 -138.6(6) . . . . ?
B1 O1 C5 C6 4.4(9) . . . . ?
B1 O1 C5 C1 -173.1(5) . . . . ?
C4 C1 C5 O1 168.6(6) . . . . ?
N1 C1 C5 O1 -11.0(8) . . . . ?
C4 C1 C5 C6 -8.8(11) . . . . ?
N1 C1 C5 C6 171.6(6) . . . . ?
O1 C5 C6 C7 6.4(9) . . . . ?
C1 C5 C6 C7 -176.3(6) . . . . ?
C5 C6 C7 O2 -1.6(9) . . . . ?
C5 C6 C7 C8 178.1(6) . . . . ?
C6 C7 O2 B1 -13.7(9) . . . . ?
C8 C7 O2 B1 166.6(5) . . . . ?
F1 B1 O2 C7 -95.5(6) . . . . ?
O1 B1 O2 C7 21.7(8) . . . . ?
C12 B1 O2 C7 140.9(5) . . . . ?
O2 C7 C8 N2 10.3(8) . . . . ?
C6 C7 C8 N2 -169.5(6) . . . . ?
O2 C7 C8 C9 -165.4(6) . . . . ?
C6 C7 C8 C9 14.8(11) . . . . ?
N2 C8 C9 C10 0.1(7) . . . . ?
C7 C8 C9 C10 176.2(6) . . . . ?
C8 C9 C10 C11 0.2(7) . . . . ?
C9 C10 C11 N2 -0.4(7) . . . . ?
C10 C11 N2 C8 0.5(7) . . . . ?
C9 C8 N2 C11 -0.3(7) . . . . ?
C7 C8 N2 C11 -176.9(6) . . . . ?
F1 B1 C12 C17 -168.8(5) . . . . ?
O2 B1 C12 C17 -47.8(7) . . . . ?
O1 B1 C12 C17 72.7(7) . . . . ?
F1 B1 C12 C13 16.6(9) . . . . ?
O2 B1 C12 C13 137.6(6) . . . . ?
O1 B1 C12 C13 -101.9(7) . . . . ?
C17 C12 C13 C14 0.2(9) . . . . ?
B1 C12 C13 C14 174.8(6) . . . . ?
C12 C13 C14 C15 -1.7(9) . . . . ?
C13 C14 C15 C16 1.1(9) . . . . ?
C14 C15 C16 C17 0.9(9) . . . . ?
C14 C15 C16 C18 179.8(6) . . . . ?
C13 C12 C17 C16 1.8(9) . . . . ?
B1 C12 C17 C16 -173.1(6) . . . . ?
C15 C16 C17 C12 -2.4(9) . . . . ?
C18 C16 C17 C12 178.6(6) . . . . ?
C15 C16 C18 O3 172.6(6) . . . . ?
C17 C16 C18 O3 -8.4(10) . . . . ?
C15 C16 C18 O4 -3.3(9) . . . . ?
C17 C16 C18 O4 175.6(5) . . . . ?

_refine_diff_density_max         0.320
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.077



####################################################################### 
# 
# 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_tm-4-6
_database_code_depnum_ccdc_archive 'CCDC 2086730'
loop_
_audit_author_name
_audit_author_address
'Nobuhiro Yasuda'
;Japan Synchrotron Radiation Research Institute
Japan
;
_audit_update_record             
;
2021-05-29 deposited with the CCDC.	2021-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 B F N2 O4, C20 H44 N, 2(C3 H6 O)'
_chemical_formula_sum            'C44 H69 B F N3 O6'
_chemical_formula_weight         765.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0021 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0007 0.0011 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0000 0.0002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0044 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   9.206(13)
_cell_length_b                   20.92(5)
_cell_length_c                   13.58(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.09(17)
_cell_angle_gamma                90
_cell_volume                     2589(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    16929
_cell_measurement_theta_min      0.911
_cell_measurement_theta_max      15.469

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.982
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.030
_shelx_estimated_absorpt_T_min   0.997
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2576
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   
;
PROCESS-AUTO (1998). Automatic Data Acquisition and Processing Package
for 2D image data. Rigaku Corporation, Tokyo, Japan.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.4275
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'BL02B1 beamline SPring-8'
_diffrn_measurement_device_type  'Pilatus3 CdTe 1M'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            17237
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         0.911
_diffrn_reflns_theta_max         15.469
_diffrn_reflns_theta_full        14.862
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.955
_reflns_number_total             9725
_reflns_number_gt                8812
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.876
_reflns_Friedel_fraction_max     0.887
_reflns_Friedel_fraction_full    0.921

_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       'Rapid Auto(Rigaku)'
_computing_cell_refinement       'Rapid Auto(Rigaku)'
_computing_data_reduction        'Rapid Auto(Rigaku)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)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_abs_structure_details 
;
 Flack x determined using 3534 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         9725
_refine_ls_number_parameters     504
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1714
_refine_ls_wR_factor_gt          0.1517
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.159
_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
C1 C 0.4824(4) 0.25933(15) 0.3774(3) 0.0365(7) Uani 1 1 d . . . . .
H1 H 0.5063 0.2156 0.3895 0.044 Uiso 1 1 calc R U . . .
C2 C 0.3989(4) 0.28493(16) 0.2867(3) 0.0400(8) Uani 1 1 d . . . . .
H2 H 0.3578 0.2610 0.2301 0.048 Uiso 1 1 calc R U . . .
C3 C 0.3902(4) 0.35524(16) 0.2994(3) 0.0373(7) Uani 1 1 d . . . . .
H3 H 0.3439 0.3849 0.2521 0.045 Uiso 1 1 calc R U . . .
C4 C 0.4671(3) 0.37038(14) 0.3995(2) 0.0301(6) Uani 1 1 d . . . . .
C5 C 0.4938(3) 0.43547(14) 0.4493(2) 0.0309(6) Uani 1 1 d . . . . .
C6 C 0.5567(3) 0.44314(14) 0.5537(2) 0.0310(6) Uani 1 1 d . . . . .
H6 H 0.5686 0.4071 0.5968 0.037 Uiso 1 1 calc R U . . .
C7 C 0.6016(3) 0.50740(14) 0.5916(2) 0.0309(6) Uani 1 1 d . . . . .
C8 C 0.6822(3) 0.51867(15) 0.6950(2) 0.0323(6) Uani 1 1 d . . . . .
C9 C 0.7448(4) 0.57840(16) 0.7411(3) 0.0372(7) Uani 1 1 d . . . . .
H9 H 0.7440 0.6191 0.7100 0.045 Uiso 1 1 calc R U . . .
C10 C 0.8083(4) 0.56339(17) 0.8436(3) 0.0417(8) Uani 1 1 d . . . . .
H10 H 0.8564 0.5924 0.8912 0.050 Uiso 1 1 calc R U . . .
C11 C 0.7837(4) 0.49545(17) 0.8586(3) 0.0388(7) Uani 1 1 d . . . . .
H11 H 0.8137 0.4726 0.9185 0.047 Uiso 1 1 calc R U . . .
C12 C 0.4916(3) 0.61290(15) 0.3529(3) 0.0342(7) Uani 1 1 d . . . . .
C13 C 0.5859(4) 0.60102(16) 0.2770(3) 0.0374(7) Uani 1 1 d . . . . .
H13 H 0.6354 0.5612 0.2765 0.045 Uiso 1 1 calc R U . . .
C14 C 0.6061(4) 0.64896(16) 0.2015(3) 0.0389(7) Uani 1 1 d . . . . .
H14 H 0.6660 0.6394 0.1519 0.047 Uiso 1 1 calc R U . . .
C15 C 0.5342(4) 0.71198(15) 0.2019(2) 0.0338(7) Uani 1 1 d . . . . .
H15 H 0.5470 0.7430 0.1527 0.041 Uiso 1 1 calc R U . . .
C16 C 0.4438(3) 0.72580(14) 0.2785(2) 0.0280(6) Uani 1 1 d . . . . .
C17 C 0.3716(3) 0.79454(14) 0.2861(2) 0.0304(6) Uani 1 1 d . . . . .
C18 C 0.4225(3) 0.67614(15) 0.3520(2) 0.0306(6) Uani 1 1 d . . . . .
H18 H 0.3612 0.6854 0.4009 0.037 Uiso 1 1 calc R U . . .
N1 N 0.5225(3) 0.31076(12) 0.4453(2) 0.0308(5) Uani 1 1 d . . . . .
H1A H 0.5727 0.3069 0.5052 0.037 Uiso 1 1 calc R U . . .
N2 N 0.7075(3) 0.46850(13) 0.7691(2) 0.0331(6) Uani 1 1 d . . . . .
H2A H 0.6805 0.4283 0.7605 0.040 Uiso 1 1 calc R U . . .
O1 O 0.4600(3) 0.48795(10) 0.38814(18) 0.0372(5) Uani 1 1 d . . . . .
O2 O 0.5776(3) 0.56104(10) 0.53178(18) 0.0361(5) Uani 1 1 d . . . . .
O3 O 0.2963(2) 0.80461(11) 0.36115(17) 0.0351(5) Uani 1 1 d . . . . .
O4 O 0.3930(3) 0.83855(11) 0.21965(19) 0.0423(6) Uani 1 1 d . . . . .
B1 B 0.4578(4) 0.55685(17) 0.4359(3) 0.0346(8) Uani 1 1 d . . . . .
F1 F 0.3125(2) 0.56627(10) 0.46886(18) 0.0469(5) Uani 1 1 d . . . . .
C19 C -0.0049(3) 0.42364(15) 0.5965(2) 0.0306(6) Uani 1 1 d . . . . .
H19 H -0.0832 0.3930 0.5709 0.037 Uiso 1 1 calc R U . . .
H19A H -0.0501 0.4571 0.6340 0.037 Uiso 1 1 calc R U . . .
C20 C 0.0539(4) 0.45643(19) 0.5043(3) 0.0418(8) Uani 1 1 d . . . . .
H20 H 0.1193 0.4263 0.4755 0.050 Uiso 1 1 calc R U . . .
H20A H 0.1120 0.4948 0.5273 0.050 Uiso 1 1 calc R U . . .
C21 C -0.0784(4) 0.47674(19) 0.4206(3) 0.0457(8) Uani 1 1 d . . . . .
H21 H -0.1520 0.5007 0.4525 0.055 Uiso 1 1 calc R U . . .
H21A H -0.0400 0.5059 0.3729 0.055 Uiso 1 1 calc R U . . .
C22 C -0.1586(5) 0.4175(2) 0.3600(3) 0.0508(9) Uani 1 1 d . . . . .
H22 H -0.1872 0.3860 0.4082 0.061 Uiso 1 1 calc R U . . .
H22A H -0.2496 0.4331 0.3196 0.061 Uiso 1 1 calc R U . . .
C23 C -0.0622(6) 0.3828(3) 0.2895(4) 0.0726(13) Uani 1 1 d . . . . .
H23 H -0.0419 0.4123 0.2371 0.109 Uiso 1 1 calc R U . . .
H23A H -0.1151 0.3454 0.2593 0.109 Uiso 1 1 calc R U . . .
H23B H 0.0305 0.3690 0.3282 0.109 Uiso 1 1 calc R U . . .
C24 C 0.1864(3) 0.32787(15) 0.6197(3) 0.0326(6) Uani 1 1 d . . . . .
H24 H 0.2598 0.3063 0.6690 0.039 Uiso 1 1 calc R U . . .
H24A H 0.2389 0.3453 0.5668 0.039 Uiso 1 1 calc R U . . .
C25 C 0.0692(4) 0.27521(16) 0.5711(3) 0.0367(7) Uani 1 1 d . . . . .
H25 H 0.0159 0.2573 0.6232 0.044 Uiso 1 1 calc R U . . .
H25A H -0.0034 0.2958 0.5202 0.044 Uiso 1 1 calc R U . . .
C26 C 0.1509(4) 0.21872(16) 0.5208(3) 0.0412(8) Uani 1 1 d . . . . .
H26 H 0.2291 0.2010 0.5708 0.049 Uiso 1 1 calc R U . . .
H26A H 0.1984 0.2367 0.4659 0.049 Uiso 1 1 calc R U . . .
C27 C 0.0433(4) 0.16166(17) 0.4777(3) 0.0462(8) Uani 1 1 d . . . . .
H27 H 0.1027 0.1276 0.4522 0.055 Uiso 1 1 calc R U . . .
H27A H -0.0026 0.1433 0.5330 0.055 Uiso 1 1 calc R U . . .
C28 C -0.0830(6) 0.1821(3) 0.3913(4) 0.0699(13) Uani 1 1 d . . . . .
H28 H -0.1482 0.2130 0.4172 0.105 Uiso 1 1 calc R U . . .
H28A H -0.1394 0.1443 0.3664 0.105 Uiso 1 1 calc R U . . .
H28B H -0.0392 0.2018 0.3369 0.105 Uiso 1 1 calc R U . . .
C29 C 0.0311(3) 0.36052(15) 0.7599(2) 0.0307(6) Uani 1 1 d . . . . .
H29 H -0.0578 0.3375 0.7293 0.037 Uiso 1 1 calc R U . . .
H29A H -0.0015 0.3978 0.7961 0.037 Uiso 1 1 calc R U . . .
C30 C 0.1248(3) 0.31385(16) 0.8390(2) 0.0342(7) Uani 1 1 d . . . . .
H30 H 0.1425 0.2726 0.8069 0.041 Uiso 1 1 calc R U . . .
H30A H 0.2209 0.3335 0.8634 0.041 Uiso 1 1 calc R U . . .
C31 C 0.0355(4) 0.30215(17) 0.9292(3) 0.0383(7) Uani 1 1 d . . . . .
H31 H -0.0639 0.2865 0.9030 0.046 Uiso 1 1 calc R U . . .
H31A H 0.0245 0.3433 0.9634 0.046 Uiso 1 1 calc R U . . .
C32 C 0.1139(4) 0.25125(18) 1.0087(3) 0.0441(8) Uani 1 1 d . . . . .
H32 H 0.1225 0.2098 0.9748 0.053 Uiso 1 1 calc R U . . .
H32A H 0.2142 0.2663 1.0336 0.053 Uiso 1 1 calc R U . . .
C33 C 0.0269(6) 0.2409(2) 1.1001(4) 0.0593(11) Uani 1 1 d . . . . .
H33 H 0.0230 0.2812 1.1363 0.089 Uiso 1 1 calc R U . . .
H33A H 0.0770 0.2085 1.1447 0.089 Uiso 1 1 calc R U . . .
H33B H -0.0731 0.2265 1.0759 0.089 Uiso 1 1 calc R U . . .
C34 C 0.2491(3) 0.43339(15) 0.7163(2) 0.0323(6) Uani 1 1 d . . . . .
H34 H 0.3251 0.4081 0.7582 0.039 Uiso 1 1 calc R U . . .
H34A H 0.2940 0.4505 0.6596 0.039 Uiso 1 1 calc R U . . .
C35 C 0.2030(4) 0.49230(17) 0.7806(3) 0.0387(7) Uani 1 1 d . . . . .
H35 H 0.1752 0.4762 0.8439 0.046 Uiso 1 1 calc R U . . .
H35A H 0.1167 0.5141 0.7436 0.046 Uiso 1 1 calc R U . . .
C36 C 0.3362(4) 0.54251(16) 0.8038(3) 0.0371(7) Uani 1 1 d . . . . .
H36 H 0.4249 0.5198 0.8355 0.045 Uiso 1 1 calc R U . . .
H36A H 0.3583 0.5611 0.7406 0.045 Uiso 1 1 calc R U . . .
C37 C 0.2974(4) 0.59879(18) 0.8756(3) 0.0463(8) Uani 1 1 d . . . . .
H37 H 0.2780 0.5799 0.9393 0.056 Uiso 1 1 calc R U . . .
H37A H 0.2063 0.6201 0.8448 0.056 Uiso 1 1 calc R U . . .
C38 C 0.4242(6) 0.6514(2) 0.8982(4) 0.0653(13) Uani 1 1 d . . . . .
H38 H 0.5132 0.6312 0.9327 0.098 Uiso 1 1 calc R U . . .
H38A H 0.3919 0.6851 0.9402 0.098 Uiso 1 1 calc R U . . .
H38B H 0.4452 0.6699 0.8354 0.098 Uiso 1 1 calc R U . . .
N3 N 0.1166(3) 0.38602(12) 0.67323(19) 0.0288(5) Uani 1 1 d . . . . .
C39 C 0.5890(7) 0.3464(3) 1.0415(4) 0.0756(15) Uani 1 1 d . . . . .
H39 H 0.5269 0.3089 1.0477 0.113 Uiso 1 1 calc R U . . .
H39A H 0.6668 0.3482 1.0986 0.113 Uiso 1 1 calc R U . . .
H39B H 0.6331 0.3431 0.9801 0.113 Uiso 1 1 calc R U . . .
C40 C 0.4943(5) 0.4080(2) 1.0383(3) 0.0531(10) Uani 1 1 d . . . . .
C41 C 0.5639(5) 0.4705(2) 1.0870(4) 0.0591(11) Uani 1 1 d . . . . .
H41 H 0.5172 0.5077 1.0519 0.089 Uiso 1 1 calc R U . . .
H41A H 0.6693 0.4710 1.0826 0.089 Uiso 1 1 calc R U . . .
H41B H 0.5490 0.4721 1.1570 0.089 Uiso 1 1 calc R U . . .
O5 O 0.3610(5) 0.4083(2) 0.9986(4) 0.1015(16) Uani 1 1 d . . . . .
C42 C 1.0473(6) 0.6269(3) 1.2307(4) 0.0686(13) Uani 1 1 d . . . . .
H42 H 1.0921 0.6631 1.2003 0.103 Uiso 1 1 calc R U . . .
H42A H 1.1070 0.6159 1.2939 0.103 Uiso 1 1 calc R U . . .
H42B H 0.9482 0.6386 1.2427 0.103 Uiso 1 1 calc R U . . .
C43 C 1.0387(4) 0.5677(2) 1.1584(3) 0.0523(9) Uani 1 1 d . . . . .
C44 C 1.1889(6) 0.5319(4) 1.1552(5) 0.0878(19) Uani 1 1 d . . . . .
H44 H 1.2258 0.5155 1.2216 0.132 Uiso 1 1 calc R U . . .
H44A H 1.2604 0.5619 1.1341 0.132 Uiso 1 1 calc R U . . .
H44B H 1.1738 0.4963 1.1080 0.132 Uiso 1 1 calc R U . . .
O6 O 0.9185(4) 0.5503(2) 1.1067(3) 0.0787(11) 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
C1 N1 1.431(5) . ?
C1 C2 1.460(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.485(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.476(5) . ?
C3 H3 0.9500 . ?
C4 N1 1.454(5) . ?
C4 C5 1.525(5) . ?
C5 O1 1.386(4) . ?
C5 C6 1.463(5) . ?
C6 C7 1.477(5) . ?
C6 H6 0.9500 . ?
C7 O2 1.384(4) . ?
C7 C8 1.512(5) . ?
C8 N2 1.450(5) . ?
C8 C9 1.478(5) . ?
C9 C10 1.466(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.458(6) . ?
C10 H10 0.9500 . ?
C11 N2 1.431(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.459(5) . ?
C12 C18 1.467(5) . ?
C12 B1 1.686(6) . ?
C13 C14 1.464(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.475(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.450(5) . ?
C15 H15 0.9500 . ?
C16 C18 1.472(5) . ?
C16 C17 1.594(5) . ?
C17 O4 1.323(4) . ?
C17 O3 1.328(4) . ?
C18 H18 0.9500 . ?
N1 H1A 0.8800 . ?
N2 H2A 0.8800 . ?
O1 B1 1.582(5) . ?
O2 B1 1.586(5) . ?
B1 F1 1.482(5) . ?
C19 C20 1.588(5) . ?
C19 N3 1.621(4) . ?
C19 H19 0.9900 . ?
C19 H19A 0.9900 . ?
C20 C21 1.603(6) . ?
C20 H20 0.9900 . ?
C20 H20A 0.9900 . ?
C21 C22 1.609(6) . ?
C21 H21 0.9900 . ?
C21 H21A 0.9900 . ?
C22 C23 1.571(7) . ?
C22 H22 0.9900 . ?
C22 H22A 0.9900 . ?
C23 H23 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C24 N3 1.597(5) . ?
C24 C25 1.617(5) . ?
C24 H24 0.9900 . ?
C24 H24A 0.9900 . ?
C25 C26 1.604(5) . ?
C25 H25 0.9900 . ?
C25 H25A 0.9900 . ?
C26 C27 1.608(6) . ?
C26 H26 0.9900 . ?
C26 H26A 0.9900 . ?
C27 C28 1.590(7) . ?
C27 H27 0.9900 . ?
C27 H27A 0.9900 . ?
C28 H28 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C29 N3 1.597(4) . ?
C29 C30 1.609(5) . ?
C29 H29 0.9900 . ?
C29 H29A 0.9900 . ?
C30 C31 1.588(5) . ?
C30 H30 0.9900 . ?
C30 H30A 0.9900 . ?
C31 C32 1.612(5) . ?
C31 H31 0.9900 . ?
C31 H31A 0.9900 . ?
C32 C33 1.584(6) . ?
C32 H32 0.9900 . ?
C32 H32A 0.9900 . ?
C33 H33 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C34 C35 1.602(5) . ?
C34 N3 1.616(4) . ?
C34 H34 0.9900 . ?
C34 H34A 0.9900 . ?
C35 C36 1.612(5) . ?
C35 H35 0.9900 . ?
C35 H35A 0.9900 . ?
C36 C37 1.601(5) . ?
C36 H36 0.9900 . ?
C36 H36A 0.9900 . ?
C37 C38 1.602(6) . ?
C37 H37 0.9900 . ?
C37 H37A 0.9900 . ?
C38 H38 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C39 C40 1.554(7) . ?
C39 H39 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C40 O5 1.269(7) . ?
C40 C41 1.562(7) . ?
C41 H41 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C42 C43 1.576(7) . ?
C42 H42 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C43 O6 1.277(6) . ?
C43 C44 1.578(7) . ?
C44 H44 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 109.0(3) . . ?
N1 C1 H1 125.5 . . ?
C2 C1 H1 125.5 . . ?
C1 C2 C3 107.2(3) . . ?
C1 C2 H2 126.4 . . ?
C3 C2 H2 126.4 . . ?
C4 C3 C2 107.0(3) . . ?
C4 C3 H3 126.5 . . ?
C2 C3 H3 126.5 . . ?
N1 C4 C3 107.7(3) . . ?
N1 C4 C5 123.4(3) . . ?
C3 C4 C5 128.8(3) . . ?
O1 C5 C6 121.3(3) . . ?
O1 C5 C4 115.6(3) . . ?
C6 C5 C4 123.0(3) . . ?
C5 C6 C7 119.3(3) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
O2 C7 C6 121.3(3) . . ?
O2 C7 C8 115.8(3) . . ?
C6 C7 C8 122.8(3) . . ?
N2 C8 C9 107.7(3) . . ?
N2 C8 C7 122.8(3) . . ?
C9 C8 C7 129.5(3) . . ?
C10 C9 C8 107.5(3) . . ?
C10 C9 H9 126.2 . . ?
C8 C9 H9 126.2 . . ?
C11 C10 C9 107.0(3) . . ?
C11 C10 H10 126.5 . . ?
C9 C10 H10 126.5 . . ?
N2 C11 C10 109.4(3) . . ?
N2 C11 H11 125.3 . . ?
C10 C11 H11 125.3 . . ?
C13 C12 C18 116.6(3) . . ?
C13 C12 B1 122.6(3) . . ?
C18 C12 B1 120.8(3) . . ?
C12 C13 C14 121.6(3) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C15 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 118.9(3) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C18 119.4(3) . . ?
C15 C16 C17 120.9(3) . . ?
C18 C16 C17 119.7(3) . . ?
O4 C17 O3 123.9(3) . . ?
O4 C17 C16 118.7(3) . . ?
O3 C17 C16 117.4(3) . . ?
C16 C18 C12 122.9(3) . . ?
C16 C18 H18 118.6 . . ?
C12 C18 H18 118.6 . . ?
C1 N1 C4 109.0(3) . . ?
C1 N1 H1A 125.5 . . ?
C4 N1 H1A 125.5 . . ?
C11 N2 C8 108.4(3) . . ?
C11 N2 H2A 125.8 . . ?
C8 N2 H2A 125.8 . . ?
C5 O1 B1 119.4(3) . . ?
C7 O2 B1 118.1(2) . . ?
F1 B1 O2 107.3(3) . . ?
F1 B1 O1 108.0(3) . . ?
O2 B1 O1 109.9(2) . . ?
F1 B1 C12 111.6(3) . . ?
O2 B1 C12 109.8(3) . . ?
O1 B1 C12 110.2(3) . . ?
C20 C19 N3 115.8(3) . . ?
C20 C19 H19 108.3 . . ?
N3 C19 H19 108.3 . . ?
C20 C19 H19A 108.3 . . ?
N3 C19 H19A 108.3 . . ?
H19 C19 H19A 107.4 . . ?
C19 C20 C21 111.4(3) . . ?
C19 C20 H20 109.3 . . ?
C21 C20 H20 109.3 . . ?
C19 C20 H20A 109.3 . . ?
C21 C20 H20A 109.3 . . ?
H20 C20 H20A 108.0 . . ?
C22 C21 C20 114.0(3) . . ?
C22 C21 H21 108.8 . . ?
C20 C21 H21 108.8 . . ?
C22 C21 H21A 108.8 . . ?
C20 C21 H21A 108.8 . . ?
H21 C21 H21A 107.6 . . ?
C23 C22 C21 114.2(4) . . ?
C23 C22 H22 108.7 . . ?
C21 C22 H22 108.7 . . ?
C23 C22 H22A 108.7 . . ?
C21 C22 H22A 108.7 . . ?
H22 C22 H22A 107.6 . . ?
C22 C23 H23 109.5 . . ?
C22 C23 H23A 109.5 . . ?
H23 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N3 C24 C25 114.7(3) . . ?
N3 C24 H24 108.6 . . ?
C25 C24 H24 108.6 . . ?
N3 C24 H24A 108.6 . . ?
C25 C24 H24A 108.6 . . ?
H24 C24 H24A 107.6 . . ?
C26 C25 C24 110.5(3) . . ?
C26 C25 H25 109.5 . . ?
C24 C25 H25 109.5 . . ?
C26 C25 H25A 109.5 . . ?
C24 C25 H25A 109.5 . . ?
H25 C25 H25A 108.1 . . ?
C25 C26 C27 113.6(3) . . ?
C25 C26 H26 108.9 . . ?
C27 C26 H26 108.9 . . ?
C25 C26 H26A 108.9 . . ?
C27 C26 H26A 108.9 . . ?
H26 C26 H26A 107.7 . . ?
C28 C27 C26 114.7(4) . . ?
C28 C27 H27 108.6 . . ?
C26 C27 H27 108.6 . . ?
C28 C27 H27A 108.6 . . ?
C26 C27 H27A 108.6 . . ?
H27 C27 H27A 107.6 . . ?
C27 C28 H28 109.5 . . ?
C27 C28 H28A 109.5 . . ?
H28 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N3 C29 C30 114.9(2) . . ?
N3 C29 H29 108.5 . . ?
C30 C29 H29 108.5 . . ?
N3 C29 H29A 108.5 . . ?
C30 C29 H29A 108.5 . . ?
H29 C29 H29A 107.5 . . ?
C31 C30 C29 108.8(3) . . ?
C31 C30 H30 109.9 . . ?
C29 C30 H30 109.9 . . ?
C31 C30 H30A 109.9 . . ?
C29 C30 H30A 109.9 . . ?
H30 C30 H30A 108.3 . . ?
C30 C31 C32 112.8(3) . . ?
C30 C31 H31 109.0 . . ?
C32 C31 H31 109.0 . . ?
C30 C31 H31A 109.0 . . ?
C32 C31 H31A 109.0 . . ?
H31 C31 H31A 107.8 . . ?
C33 C32 C31 112.8(3) . . ?
C33 C32 H32 109.0 . . ?
C31 C32 H32 109.0 . . ?
C33 C32 H32A 109.0 . . ?
C31 C32 H32A 109.0 . . ?
H32 C32 H32A 107.8 . . ?
C32 C33 H33 109.5 . . ?
C32 C33 H33A 109.5 . . ?
H33 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C35 C34 N3 115.1(3) . . ?
C35 C34 H34 108.5 . . ?
N3 C34 H34 108.5 . . ?
C35 C34 H34A 108.5 . . ?
N3 C34 H34A 108.5 . . ?
H34 C34 H34A 107.5 . . ?
C34 C35 C36 110.8(3) . . ?
C34 C35 H35 109.5 . . ?
C36 C35 H35 109.5 . . ?
C34 C35 H35A 109.5 . . ?
C36 C35 H35A 109.5 . . ?
H35 C35 H35A 108.1 . . ?
C37 C36 C35 111.7(3) . . ?
C37 C36 H36 109.3 . . ?
C35 C36 H36 109.3 . . ?
C37 C36 H36A 109.3 . . ?
C35 C36 H36A 109.3 . . ?
H36 C36 H36A 107.9 . . ?
C36 C37 C38 113.7(4) . . ?
C36 C37 H37 108.8 . . ?
C38 C37 H37 108.8 . . ?
C36 C37 H37A 108.8 . . ?
C38 C37 H37A 108.8 . . ?
H37 C37 H37A 107.7 . . ?
C37 C38 H38 109.5 . . ?
C37 C38 H38A 109.5 . . ?
H38 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C29 N3 C24 110.6(3) . . ?
C29 N3 C34 111.3(2) . . ?
C24 N3 C34 107.5(2) . . ?
C29 N3 C19 105.6(2) . . ?
C24 N3 C19 111.3(2) . . ?
C34 N3 C19 110.6(3) . . ?
C40 C39 H39 109.5 . . ?
C40 C39 H39A 109.5 . . ?
H39 C39 H39A 109.5 . . ?
C40 C39 H39B 109.5 . . ?
H39 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
O5 C40 C41 119.4(4) . . ?
O5 C40 C39 121.4(5) . . ?
C41 C40 C39 119.2(4) . . ?
C40 C41 H41 109.5 . . ?
C40 C41 H41A 109.5 . . ?
H41 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C43 C42 H42 109.5 . . ?
C43 C42 H42A 109.5 . . ?
H42 C42 H42A 109.5 . . ?
C43 C42 H42B 109.5 . . ?
H42 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
O6 C43 C44 123.0(5) . . ?
O6 C43 C42 122.0(4) . . ?
C44 C43 C42 114.9(4) . . ?
C43 C44 H44 109.5 . . ?
C43 C44 H44A 109.5 . . ?
H44 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 1.0(4) . . . . ?
C1 C2 C3 C4 -1.1(4) . . . . ?
C2 C3 C4 N1 0.8(4) . . . . ?
C2 C3 C4 C5 178.3(3) . . . . ?
N1 C4 C5 O1 167.2(3) . . . . ?
C3 C4 C5 O1 -10.0(5) . . . . ?
N1 C4 C5 C6 -10.3(5) . . . . ?
C3 C4 C5 C6 172.5(3) . . . . ?
O1 C5 C6 C7 -7.4(4) . . . . ?
C4 C5 C6 C7 170.0(3) . . . . ?
C5 C6 C7 O2 3.7(4) . . . . ?
C5 C6 C7 C8 -173.3(3) . . . . ?
O2 C7 C8 N2 175.8(3) . . . . ?
C6 C7 C8 N2 -7.1(4) . . . . ?
O2 C7 C8 C9 -2.6(5) . . . . ?
C6 C7 C8 C9 174.5(3) . . . . ?
N2 C8 C9 C10 0.2(4) . . . . ?
C7 C8 C9 C10 178.8(3) . . . . ?
C8 C9 C10 C11 -0.1(4) . . . . ?
C9 C10 C11 N2 0.0(4) . . . . ?
C18 C12 C13 C14 -2.2(4) . . . . ?
B1 C12 C13 C14 175.9(3) . . . . ?
C12 C13 C14 C15 1.8(5) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C14 C15 C16 C18 -1.8(4) . . . . ?
C14 C15 C16 C17 176.3(3) . . . . ?
C15 C16 C17 O4 1.5(4) . . . . ?
C18 C16 C17 O4 179.6(3) . . . . ?
C15 C16 C17 O3 -176.8(3) . . . . ?
C18 C16 C17 O3 1.4(4) . . . . ?
C15 C16 C18 C12 1.4(4) . . . . ?
C17 C16 C18 C12 -176.8(3) . . . . ?
C13 C12 C18 C16 0.6(4) . . . . ?
B1 C12 C18 C16 -177.5(3) . . . . ?
C2 C1 N1 C4 -0.5(4) . . . . ?
C3 C4 N1 C1 -0.2(3) . . . . ?
C5 C4 N1 C1 -177.9(3) . . . . ?
C10 C11 N2 C8 0.1(4) . . . . ?
C9 C8 N2 C11 -0.2(3) . . . . ?
C7 C8 N2 C11 -178.9(3) . . . . ?
C6 C5 O1 B1 -12.9(4) . . . . ?
C4 C5 O1 B1 169.6(3) . . . . ?
C6 C7 O2 B1 19.7(4) . . . . ?
C8 C7 O2 B1 -163.1(3) . . . . ?
C7 O2 B1 F1 80.9(3) . . . . ?
C7 O2 B1 O1 -36.3(4) . . . . ?
C7 O2 B1 C12 -157.6(3) . . . . ?
C5 O1 B1 F1 -83.7(4) . . . . ?
C5 O1 B1 O2 33.1(4) . . . . ?
C5 O1 B1 C12 154.1(3) . . . . ?
C13 C12 B1 F1 -151.6(3) . . . . ?
C18 C12 B1 F1 26.4(4) . . . . ?
C13 C12 B1 O2 89.5(4) . . . . ?
C18 C12 B1 O2 -92.5(3) . . . . ?
C13 C12 B1 O1 -31.6(4) . . . . ?
C18 C12 B1 O1 146.4(3) . . . . ?
N3 C19 C20 C21 165.9(3) . . . . ?
C19 C20 C21 C22 -72.1(4) . . . . ?
C20 C21 C22 C23 -69.3(5) . . . . ?
N3 C24 C25 C26 -179.3(3) . . . . ?
C24 C25 C26 C27 175.7(3) . . . . ?
C25 C26 C27 C28 62.1(5) . . . . ?
N3 C29 C30 C31 170.6(3) . . . . ?
C29 C30 C31 C32 175.3(3) . . . . ?
C30 C31 C32 C33 178.5(3) . . . . ?
N3 C34 C35 C36 -170.4(3) . . . . ?
C34 C35 C36 C37 -175.2(3) . . . . ?
C35 C36 C37 C38 -178.1(4) . . . . ?
C30 C29 N3 C24 52.3(3) . . . . ?
C30 C29 N3 C34 -67.1(3) . . . . ?
C30 C29 N3 C19 172.8(2) . . . . ?
C25 C24 N3 C29 58.6(3) . . . . ?
C25 C24 N3 C34 -179.7(3) . . . . ?
C25 C24 N3 C19 -58.4(3) . . . . ?
C35 C34 N3 C29 -54.1(3) . . . . ?
C35 C34 N3 C24 -175.3(3) . . . . ?
C35 C34 N3 C19 63.0(3) . . . . ?
C20 C19 N3 C29 177.7(3) . . . . ?
C20 C19 N3 C24 -62.2(3) . . . . ?
C20 C19 N3 C34 57.2(3) . . . . ?

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.048



####################################################################### 
# 
# 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_ydkr_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2086722'
loop_
_audit_author_name
_audit_author_address
'Nobuhiro Yasuda'
;Japan Synchrotron Radiation Research Institute
Japan
;
_audit_update_record             
;
2021-05-29 deposited with the CCDC.	2021-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 B F N2 O4'
_chemical_formula_sum            'C18 H14 B F N2 O4'
_chemical_formula_weight         352.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0045 0.0022 '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 0.0085 0.0044 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0146 0.0081 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0231 0.0137 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0022 0.0009 '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'

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

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

_cell_length_a                   5.8897(3)
_cell_length_b                   15.6222(7)
_cell_length_c                   18.0449(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.961(3)
_cell_angle_gamma                90
_cell_volume                     1648.07(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    17257
_cell_measurement_theta_min      1.973
_cell_measurement_theta_max      29.236

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.010
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    0.145
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.763
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'ABSCOR (T.Higashi, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.81088
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'synchrotron radiation SPring-8 BL40XU'
_diffrn_radiation_monochromator  'Si(111) Channel Cut'
_diffrn_measurement_device_type  'DECTRIS EIGER X 1M'
_diffrn_measurement_method       'Shutterless ω scans'
_diffrn_detector_area_resol_mean 13.33
_diffrn_reflns_number            17257
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.973
_diffrn_reflns_theta_max         29.236
_diffrn_reflns_theta_full        29.113
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3011
_reflns_number_gt                2656
_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       'Rapid Auto(Rigaku)'
_computing_cell_refinement       'Rapid Auto(Rigaku)'
_computing_data_reduction        'Rapid Auto(Rigaku)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0511P)²+1.1165P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0134(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3011
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1194
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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
C1 C -0.1588(3) 0.73552(12) 0.77812(11) 0.0292(5) Uani 1 1 d . . . . .
H1 H -0.2960 0.7681 0.7720 0.035 Uiso 1 1 calc R U . . .
C2 C -0.0244(4) 0.72015(13) 0.84463(11) 0.0311(5) Uani 1 1 d . . . . .
H2 H -0.0519 0.7402 0.8924 0.037 Uiso 1 1 calc R U . . .
C3 C 0.1605(4) 0.66948(12) 0.82887(11) 0.0284(4) Uani 1 1 d . . . . .
H3 H 0.2815 0.6492 0.8641 0.034 Uiso 1 1 calc R U . . .
C4 C 0.1350(3) 0.65452(11) 0.75294(10) 0.0232(4) Uani 1 1 d . . . . .
C5 C 0.2667(3) 0.60783(11) 0.70492(10) 0.0221(4) Uani 1 1 d . . . . .
C6 C 0.4753(3) 0.56848(11) 0.72843(11) 0.0243(4) Uani 1 1 d . . . . .
H6 H 0.5473 0.5759 0.7780 0.029 Uiso 1 1 calc R U . . .
C7 C 0.5764(3) 0.51792(11) 0.67782(10) 0.0225(4) Uani 1 1 d . . . . .
C8 C 0.7771(3) 0.46722(11) 0.69729(11) 0.0241(4) Uani 1 1 d . . . . .
C9 C 0.9070(3) 0.45094(12) 0.76491(12) 0.0280(4) Uani 1 1 d . . . . .
H9 H 0.8749 0.4697 0.8126 0.034 Uiso 1 1 calc R U . . .
C10 C 1.0952(3) 0.40162(12) 0.74988(12) 0.0300(5) Uani 1 1 d . . . . .
H10 H 1.2139 0.3806 0.7856 0.036 Uiso 1 1 calc R U . . .
C11 C 1.0763(3) 0.38920(12) 0.67388(12) 0.0289(5) Uani 1 1 d . . . . .
H11 H 1.1814 0.3586 0.6479 0.035 Uiso 1 1 calc R U . . .
C12 C 0.4775(3) 0.66989(11) 0.56297(10) 0.0212(4) Uani 1 1 d . . . . .
C13 C 0.4006(3) 0.75082(12) 0.58184(11) 0.0253(4) Uani 1 1 d . . . . .
H13 H 0.2632 0.7553 0.6042 0.030 Uiso 1 1 calc R U . . .
C14 C 0.5194(3) 0.82445(12) 0.56872(11) 0.0267(4) Uani 1 1 d . . . . .
H14 H 0.4628 0.8787 0.5816 0.032 Uiso 1 1 calc R U . . .
C15 C 0.7216(3) 0.81903(12) 0.53665(10) 0.0236(4) Uani 1 1 d . . . . .
C16 C 0.8480(3) 0.89790(12) 0.52192(10) 0.0260(4) Uani 1 1 d . . . . .
C17 C 0.8027(3) 0.73928(12) 0.51700(10) 0.0252(4) Uani 1 1 d . . . . .
H17 H 0.9400 0.7353 0.4945 0.030 Uiso 1 1 calc R U . . .
C18 C 0.6815(3) 0.66581(11) 0.53056(10) 0.0224(4) Uani 1 1 d . . . . .
H18 H 0.7383 0.6116 0.5176 0.027 Uiso 1 1 calc R U . . .
N1 N -0.0615(3) 0.69621(10) 0.72301(9) 0.0251(4) Uani 1 1 d . . . . .
H1A H -0.1154 0.6971 0.6754 0.030 Uiso 1 1 calc R U . . .
N2 N 0.8832(3) 0.42785(10) 0.64238(9) 0.0253(4) Uani 1 1 d . . . . .
H2A H 0.8330 0.4279 0.5944 0.030 Uiso 1 1 calc R U . . .
O1 O 0.1751(2) 0.60381(8) 0.63483(7) 0.0227(3) Uani 1 1 d . . . . .
O2 O 0.4908(2) 0.51434(8) 0.60706(7) 0.0230(3) Uani 1 1 d . . . . .
O3 O 0.7737(3) 0.96780(9) 0.54988(9) 0.0379(4) Uani 1 1 d . . . . .
H3A H 0.8475 1.0098 0.5364 0.057 Uiso 1 1 calc R U . . .
O4 O 1.0128(2) 0.89562(9) 0.48494(8) 0.0329(4) Uani 1 1 d . . . . .
B1 B 0.3335(4) 0.58488(13) 0.57846(12) 0.0226(5) Uani 1 1 d . . . . .
F1 F 0.20001(18) 0.55489(7) 0.51509(6) 0.0259(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
C1 N1 1.354(2) . ?
C1 C2 1.376(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.403(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 N1 1.380(2) . ?
C4 C5 1.431(3) . ?
C5 O1 1.315(2) . ?
C5 C6 1.393(3) . ?
C6 C7 1.395(3) . ?
C6 H6 0.9500 . ?
C7 O2 1.316(2) . ?
C7 C8 1.431(3) . ?
C8 N2 1.379(2) . ?
C8 C9 1.383(3) . ?
C9 C10 1.403(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(3) . ?
C10 H10 0.9500 . ?
C11 N2 1.351(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.399(3) . ?
C12 C18 1.400(3) . ?
C12 B1 1.618(3) . ?
C13 C14 1.382(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(3) . ?
C14 H14 0.9500 . ?
C15 C17 1.395(3) . ?
C15 C16 1.480(3) . ?
C16 O4 1.243(2) . ?
C16 O3 1.301(2) . ?
C17 C18 1.389(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N1 H1A 0.8800 . ?
N2 H2A 0.8800 . ?
O1 B1 1.491(2) . ?
O2 B1 1.491(2) . ?
O3 H3A 0.8400 . ?
B1 F1 1.388(2) . ?

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
N1 C1 C2 108.16(18) . . ?
N1 C1 H1 125.9 . . ?
C2 C1 H1 125.9 . . ?
C1 C2 C3 107.47(18) . . ?
C1 C2 H2 126.3 . . ?
C3 C2 H2 126.3 . . ?
C4 C3 C2 107.63(18) . . ?
C4 C3 H3 126.2 . . ?
C2 C3 H3 126.2 . . ?
C3 C4 N1 107.08(16) . . ?
C3 C4 C5 133.30(18) . . ?
N1 C4 C5 119.61(17) . . ?
O1 C5 C6 121.04(17) . . ?
O1 C5 C4 114.69(16) . . ?
C6 C5 C4 124.27(17) . . ?
C5 C6 C7 118.78(18) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
O2 C7 C6 121.04(17) . . ?
O2 C7 C8 115.01(16) . . ?
C6 C7 C8 123.95(18) . . ?
N2 C8 C9 107.55(17) . . ?
N2 C8 C7 120.22(17) . . ?
C9 C8 C7 132.13(18) . . ?
C8 C9 C10 107.21(18) . . ?
C8 C9 H9 126.4 . . ?
C10 C9 H9 126.4 . . ?
C11 C10 C9 107.43(18) . . ?
C11 C10 H10 126.3 . . ?
C9 C10 H10 126.3 . . ?
N2 C11 C10 108.60(18) . . ?
N2 C11 H11 125.7 . . ?
C10 C11 H11 125.7 . . ?
C13 C12 C18 117.55(16) . . ?
C13 C12 B1 120.51(16) . . ?
C18 C12 B1 121.94(16) . . ?
C14 C13 C12 121.66(18) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 119.91(18) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C17 119.83(17) . . ?
C14 C15 C16 119.97(17) . . ?
C17 C15 C16 120.18(17) . . ?
O4 C16 O3 123.61(17) . . ?
O4 C16 C15 120.98(17) . . ?
O3 C16 C15 115.41(17) . . ?
C18 C17 C15 119.61(17) . . ?
C18 C17 H17 120.2 . . ?
C15 C17 H17 120.2 . . ?
C17 C18 C12 121.42(17) . . ?
C17 C18 H18 119.3 . . ?
C12 C18 H18 119.3 . . ?
C1 N1 C4 109.65(16) . . ?
C1 N1 H1A 125.2 . . ?
C4 N1 H1A 125.2 . . ?
C11 N2 C8 109.19(17) . . ?
C11 N2 H2A 125.4 . . ?
C8 N2 H2A 125.4 . . ?
C5 O1 B1 116.62(15) . . ?
C7 O2 B1 116.96(14) . . ?
C16 O3 H3A 109.5 . . ?
F1 B1 O1 106.87(15) . . ?
F1 B1 O2 107.57(15) . . ?
O1 B1 O2 108.94(15) . . ?
F1 B1 C12 113.02(16) . . ?
O1 B1 C12 109.84(15) . . ?
O2 B1 C12 110.46(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
N1 C1 C2 C3 -0.1(2) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C2 C3 C4 N1 0.5(2) . . . . ?
C2 C3 C4 C5 -179.8(2) . . . . ?
C3 C4 C5 O1 175.45(19) . . . . ?
N1 C4 C5 O1 -4.9(2) . . . . ?
C3 C4 C5 C6 -4.2(3) . . . . ?
N1 C4 C5 C6 175.43(16) . . . . ?
O1 C5 C6 C7 -5.7(3) . . . . ?
C4 C5 C6 C7 173.89(17) . . . . ?
C5 C6 C7 O2 7.2(3) . . . . ?
C5 C6 C7 C8 -173.20(17) . . . . ?
O2 C7 C8 N2 8.0(2) . . . . ?
C6 C7 C8 N2 -171.60(16) . . . . ?
O2 C7 C8 C9 -176.18(18) . . . . ?
C6 C7 C8 C9 4.2(3) . . . . ?
N2 C8 C9 C10 0.6(2) . . . . ?
C7 C8 C9 C10 -175.64(19) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 N2 -0.8(2) . . . . ?
C18 C12 C13 C14 0.5(3) . . . . ?
B1 C12 C13 C14 -179.52(18) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 C17 0.7(3) . . . . ?
C13 C14 C15 C16 179.44(17) . . . . ?
C14 C15 C16 O4 -170.88(18) . . . . ?
C17 C15 C16 O4 7.8(3) . . . . ?
C14 C15 C16 O3 8.9(3) . . . . ?
C17 C15 C16 O3 -172.41(18) . . . . ?
C14 C15 C17 C18 -0.8(3) . . . . ?
C16 C15 C17 C18 -179.47(17) . . . . ?
C15 C17 C18 C12 0.7(3) . . . . ?
C13 C12 C18 C17 -0.5(3) . . . . ?
B1 C12 C18 C17 179.49(17) . . . . ?
C2 C1 N1 C4 0.5(2) . . . . ?
C3 C4 N1 C1 -0.6(2) . . . . ?
C5 C4 N1 C1 179.65(16) . . . . ?
C10 C11 N2 C8 1.2(2) . . . . ?
C9 C8 N2 C11 -1.1(2) . . . . ?
C7 C8 N2 C11 175.64(16) . . . . ?
C6 C5 O1 B1 -21.6(2) . . . . ?
C4 C5 O1 B1 158.76(15) . . . . ?
C6 C7 O2 B1 18.9(2) . . . . ?
C8 C7 O2 B1 -160.76(15) . . . . ?
C5 O1 B1 F1 159.95(14) . . . . ?
C5 O1 B1 O2 44.0(2) . . . . ?
C5 O1 B1 C12 -77.10(19) . . . . ?
C7 O2 B1 F1 -158.17(14) . . . . ?
C7 O2 B1 O1 -42.7(2) . . . . ?
C7 O2 B1 C12 78.05(19) . . . . ?
C13 C12 B1 F1 100.1(2) . . . . ?
C18 C12 B1 F1 -79.9(2) . . . . ?
C13 C12 B1 O1 -19.1(2) . . . . ?
C18 C12 B1 O1 160.88(16) . . . . ?
C13 C12 B1 O2 -139.33(17) . . . . ?
C18 C12 B1 O2 40.7(2) . . . . ?

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.054



####################################################################### 
# 
# 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_60622m
_database_code_depnum_ccdc_archive 'CCDC 2086723'
loop_
_audit_author_name
_audit_author_address
'Nobuhiro Yasuda'
;Japan Synchrotron Radiation Research Institute
Japan
;
_audit_update_record             
;
2021-05-29 deposited with the CCDC.	2021-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 B F N2 O4, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C20 H18 B F N2 O5'
_chemical_formula_weight         396.17

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

_space_group_crystal_system      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                   12.248(4)
_cell_length_b                   12.839(3)
_cell_length_c                   14.136(3)
_cell_angle_alpha                109.1030(10)
_cell_angle_beta                 99.474(9)
_cell_angle_gamma                108.353(7)
_cell_volume                     1902.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    24867
_cell_measurement_theta_min      6.652
_cell_measurement_theta_max      68.342

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.886
_shelx_estimated_absorpt_T_min   0.789
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            24867
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         6.652
_diffrn_reflns_theta_max         68.342
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             6763
_reflns_number_gt                5900
_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       'Rapid Auto(Rigaku)'
_computing_cell_refinement       'Rapid Auto(Rigaku)'
_computing_data_reduction        'Rapid Auto(Rigaku)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0552P)²+0.6014P] 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         6763
_refine_ls_number_parameters     523
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0986
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
C1 C 0.10980(13) -0.26392(13) 1.07787(12) 0.0243(3) Uani 1 1 d . . . . .
H1 H 0.1031 -0.3439 1.0622 0.029 Uiso 1 1 calc R U . . .
C2 C 0.09542(14) -0.19069(14) 1.16662(12) 0.0270(3) Uani 1 1 d . . . . .
H2 H 0.0783 -0.2102 1.2233 0.032 Uiso 1 1 calc R U . . .
C3 C 0.11070(13) -0.08234(13) 1.15767(11) 0.0240(3) Uani 1 1 d . . . . .
H3 H 0.1051 -0.0147 1.2070 0.029 Uiso 1 1 calc R U . . .
C4 C 0.13554(12) -0.09129(12) 1.06374(10) 0.0187(3) Uani 1 1 d . . . . .
N1 N 0.13487(10) -0.20350(10) 1.01683(9) 0.0204(2) Uani 1 1 d . . . . .
H4 H 0.1487 -0.2317 0.9563 0.024 Uiso 1 1 calc R U . . .
C5 C 0.15789(12) -0.00805(12) 1.01514(10) 0.0175(3) Uani 1 1 d . . . . .
C6 C 0.15036(12) 0.10242(12) 1.05579(10) 0.0191(3) Uani 1 1 d . . . . .
H5 H 0.1265 0.1252 1.1175 0.023 Uiso 1 1 calc R U . . .
C7 C 0.17796(12) 0.17947(12) 1.00561(10) 0.0179(3) Uani 1 1 d . . . . .
C8 C 0.17730(12) 0.29716(12) 1.04361(11) 0.0205(3) Uani 1 1 d . . . . .
C9 C 0.15392(14) 0.36210(13) 1.13189(12) 0.0265(3) Uani 1 1 d . . . . .
H6 H 0.1335 0.3362 1.1847 0.032 Uiso 1 1 calc R U . . .
C10 C 0.16589(15) 0.47272(14) 1.12876(13) 0.0322(4) Uani 1 1 d . . . . .
H7 H 0.1552 0.5359 1.1791 0.039 Uiso 1 1 calc R U . . .
C11 C 0.19611(14) 0.47318(13) 1.03921(13) 0.0302(3) Uani 1 1 d . . . . .
H8 H 0.2096 0.5372 1.0170 0.036 Uiso 1 1 calc R U . . .
N2 N 0.20335(11) 0.36780(10) 0.98836(10) 0.0238(3) Uani 1 1 d . . . . .
H9 H 0.2218 0.3473 0.9292 0.029 Uiso 1 1 calc R U . . .
O1 O 0.18766(9) -0.04371(8) 0.92825(7) 0.0222(2) Uani 1 1 d . . . . .
O2 O 0.21072(9) 0.15009(8) 0.92013(7) 0.0214(2) Uani 1 1 d . . . . .
B1 B 0.20754(15) 0.02753(13) 0.86275(12) 0.0192(3) Uani 1 1 d . . . . .
F1 F 0.10629(7) -0.02965(7) 0.77286(6) 0.02363(19) Uani 1 1 d . . . . .
C12 C 0.33087(13) 0.04065(11) 0.83509(10) 0.0185(3) Uani 1 1 d . . . . .
C13 C 0.34747(12) 0.05562(11) 0.74413(10) 0.0187(3) Uani 1 1 d . . . . .
H10 H 0.2810 0.0486 0.6936 0.022 Uiso 1 1 calc R U . . .
C14 C 0.45946(13) 0.08056(12) 0.72603(11) 0.0199(3) Uani 1 1 d . . . . .
C15 C 0.55783(14) 0.08931(13) 0.79812(12) 0.0243(3) Uani 1 1 d . . . . .
H11 H 0.6343 0.1063 0.7860 0.029 Uiso 1 1 calc R U . . .
C16 C 0.54244(14) 0.07288(14) 0.88784(12) 0.0265(3) Uani 1 1 d . . . . .
H12 H 0.6085 0.0776 0.9373 0.032 Uiso 1 1 calc R U . . .
C17 C 0.43124(13) 0.04964(13) 0.90577(11) 0.0232(3) Uani 1 1 d . . . . .
H13 H 0.4229 0.0395 0.9682 0.028 Uiso 1 1 calc R U . . .
C18 C 0.47413(13) 0.10270(13) 0.63151(11) 0.0224(3) Uani 1 1 d . . . . .
O3 O 0.39118(9) 0.10110(10) 0.56789(8) 0.0276(2) Uani 1 1 d . . . . .
O4 O 0.58304(10) 0.12531(11) 0.62219(9) 0.0339(3) Uani 1 1 d . . . . .
H14 H 0.5852 0.1369 0.5673 0.051 Uiso 1 1 calc R U . . .
C19 C 0.97922(14) 0.88726(12) 0.37766(11) 0.0241(3) Uani 1 1 d . . . . .
H15 H 0.9423 0.9363 0.3605 0.029 Uiso 1 1 calc R U . . .
C20 C 1.09587(14) 0.92710(13) 0.43905(11) 0.0244(3) Uani 1 1 d . . . . .
H16 H 1.1531 1.0079 0.4718 0.029 Uiso 1 1 calc R U . . .
C21 C 1.11458(13) 0.82708(12) 0.44430(11) 0.0216(3) Uani 1 1 d . . . . .
H17 H 1.1868 0.8271 0.4812 0.026 Uiso 1 1 calc R U . . .
C22 C 1.00742(13) 0.72724(12) 0.38522(10) 0.0193(3) Uani 1 1 d . . . . .
N3 N 0.92609(11) 0.76732(10) 0.34597(9) 0.0205(2) Uani 1 1 d . . . . .
H36 H 0.8512 0.7218 0.3064 0.025 Uiso 1 1 calc R U . . .
C23 C 0.97696(12) 0.60236(12) 0.35881(10) 0.0183(3) Uani 1 1 d . . . . .
C24 C 1.06039(13) 0.55712(12) 0.38779(10) 0.0203(3) Uani 1 1 d . . . . .
H18 H 1.1422 0.6094 0.4250 0.024 Uiso 1 1 calc R U . . .
C25 C 1.02273(12) 0.43535(12) 0.36168(10) 0.0191(3) Uani 1 1 d . . . . .
O5 O 0.86456(8) 0.53181(8) 0.30445(7) 0.0201(2) Uani 1 1 d . . . . .
O6 O 0.91057(9) 0.36028(8) 0.30743(8) 0.0222(2) Uani 1 1 d . . . . .
C26 C 1.10060(13) 0.38028(12) 0.38976(10) 0.0202(3) Uani 1 1 d . . . . .
C27 C 1.22260(13) 0.42701(13) 0.44116(11) 0.0255(3) Uani 1 1 d . . . . .
H19 H 1.2753 0.5095 0.4729 0.031 Uiso 1 1 calc R U . . .
C28 C 1.25395(15) 0.33029(14) 0.43780(12) 0.0311(4) Uani 1 1 d . . . . .
H20 H 1.3321 0.3348 0.4661 0.037 Uiso 1 1 calc R U . . .
C29 C 1.15083(15) 0.22771(14) 0.38605(12) 0.0297(3) Uani 1 1 d . . . . .
H21 H 1.1452 0.1485 0.3729 0.036 Uiso 1 1 calc R U . . .
N4 N 1.05885(11) 0.25804(10) 0.35694(9) 0.0244(3) Uani 1 1 d . . . . .
H22 H 0.9838 0.2073 0.3223 0.029 Uiso 1 1 calc R U . . .
C30 C 0.69253(12) 0.33020(11) 0.24629(10) 0.0190(3) Uani 1 1 d . . . . .
C31 C 0.66523(12) 0.28573(12) 0.32086(10) 0.0192(3) Uani 1 1 d . . . . .
H23 H 0.7291 0.2912 0.3730 0.023 Uiso 1 1 calc R U . . .
C32 C 0.54730(12) 0.23367(12) 0.32125(10) 0.0194(3) Uani 1 1 d . . . . .
C33 C 0.45206(13) 0.22336(13) 0.24495(11) 0.0248(3) Uani 1 1 d . . . . .
H24 H 0.3712 0.1886 0.2452 0.030 Uiso 1 1 calc R U . . .
C34 C 0.47723(14) 0.26473(15) 0.16862(12) 0.0311(4) Uani 1 1 d . . . . .
H25 H 0.4131 0.2571 0.1153 0.037 Uiso 1 1 calc R U . . .
C35 C 0.59542(13) 0.31712(13) 0.16977(11) 0.0266(3) Uani 1 1 d . . . . .
H26 H 0.6108 0.3450 0.1168 0.032 Uiso 1 1 calc R U . . .
C36 C 0.52559(13) 0.19043(12) 0.40428(11) 0.0213(3) Uani 1 1 d . . . . .
O7 O 0.60866(9) 0.19642(11) 0.47076(8) 0.0305(3) Uani 1 1 d . . . . .
O8 O 0.41233(9) 0.14738(9) 0.40237(8) 0.0263(2) Uani 1 1 d . . . . .
H27 H 0.4075 0.1246 0.4515 0.039 Uiso 1 1 calc R U . . .
C37 C 0.47959(14) 0.35499(13) 0.93524(11) 0.0253(3) Uani 1 1 d . . . . .
H28 H 0.5638 0.3715 0.9371 0.038 Uiso 1 1 calc R U . . .
H29 H 0.4764 0.4142 0.9983 0.038 Uiso 1 1 calc R U . . .
H30 H 0.4410 0.2743 0.9328 0.038 Uiso 1 1 calc R U . . .
C38 C 0.41466(13) 0.36261(12) 0.83987(11) 0.0221(3) Uani 1 1 d . . . . .
O9 O 0.30905(9) 0.34664(9) 0.81601(8) 0.0262(2) Uani 1 1 d . . . . .
O10 O 0.48719(9) 0.38956(10) 0.78392(8) 0.0295(2) Uani 1 1 d . . . . .
C39 C 0.43519(15) 0.39963(15) 0.68842(12) 0.0313(4) Uani 1 1 d . . . . .
H31 H 0.3929 0.4546 0.7033 0.038 Uiso 1 1 calc R U . . .
H32 H 0.3772 0.3201 0.6349 0.038 Uiso 1 1 calc R U . . .
C40 C 0.54045(16) 0.44898(17) 0.65096(14) 0.0424(4) Uani 1 1 d . . . . .
H33 H 0.5113 0.4580 0.5864 0.064 Uiso 1 1 calc R U . . .
H34 H 0.5970 0.5274 0.7051 0.064 Uiso 1 1 calc R U . . .
H35 H 0.5814 0.3937 0.6371 0.064 Uiso 1 1 calc R U . . .
F2 F 0.84295(8) 0.37737(7) 0.15003(6) 0.02539(19) Uani 1 1 d . . . . .
B2 B 0.82781(15) 0.39878(14) 0.25077(12) 0.0202(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
C1 N1 1.3475(18) . ?
C1 C2 1.376(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.395(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(2) . ?
C3 H3 0.9500 . ?
C4 N1 1.3715(18) . ?
C4 C5 1.4308(19) . ?
N1 H4 0.8800 . ?
C5 O1 1.3175(16) . ?
C5 C6 1.3844(19) . ?
C6 C7 1.3871(19) . ?
C6 H5 0.9500 . ?
C7 O2 1.3114(17) . ?
C7 C8 1.4316(19) . ?
C8 N2 1.3777(18) . ?
C8 C9 1.386(2) . ?
C9 C10 1.397(2) . ?
C9 H6 0.9500 . ?
C10 C11 1.377(2) . ?
C10 H7 0.9500 . ?
C11 N2 1.3473(19) . ?
C11 H8 0.9500 . ?
N2 H9 0.8800 . ?
O1 B1 1.4972(17) . ?
O2 B1 1.5003(18) . ?
B1 F1 1.4102(18) . ?
B1 C12 1.594(2) . ?
C12 C17 1.398(2) . ?
C12 C13 1.3981(19) . ?
C13 C14 1.394(2) . ?
C13 H10 0.9500 . ?
C14 C15 1.392(2) . ?
C14 C18 1.4812(19) . ?
C15 C16 1.385(2) . ?
C15 H11 0.9500 . ?
C16 C17 1.384(2) . ?
C16 H12 0.9500 . ?
C17 H13 0.9500 . ?
C18 O3 1.2309(17) . ?
C18 O4 1.3114(19) . ?
O4 H14 0.8400 . ?
C19 N3 1.3480(18) . ?
C19 C20 1.377(2) . ?
C19 H15 0.9500 . ?
C20 C21 1.396(2) . ?
C20 H16 0.9500 . ?
C21 C22 1.394(2) . ?
C21 H17 0.9500 . ?
C22 N3 1.3758(18) . ?
C22 C23 1.4264(19) . ?
N3 H36 0.8800 . ?
C23 O5 1.3104(17) . ?
C23 C24 1.393(2) . ?
C24 C25 1.380(2) . ?
C24 H18 0.9500 . ?
C25 O6 1.3191(17) . ?
C25 C26 1.432(2) . ?
O5 B2 1.5002(18) . ?
O6 B2 1.4901(18) . ?
C26 N4 1.3710(18) . ?
C26 C27 1.383(2) . ?
C27 C28 1.400(2) . ?
C27 H19 0.9500 . ?
C28 C29 1.372(2) . ?
C28 H20 0.9500 . ?
C29 N4 1.348(2) . ?
C29 H21 0.9500 . ?
N4 H22 0.8800 . ?
C30 C31 1.3924(19) . ?
C30 C35 1.395(2) . ?
C30 B2 1.592(2) . ?
C31 C32 1.389(2) . ?
C31 H23 0.9500 . ?
C32 C33 1.391(2) . ?
C32 C36 1.4808(19) . ?
C33 C34 1.387(2) . ?
C33 H24 0.9500 . ?
C34 C35 1.386(2) . ?
C34 H25 0.9500 . ?
C35 H26 0.9500 . ?
C36 O7 1.2300(17) . ?
C36 O8 1.3137(18) . ?
O8 H27 0.8400 . ?
C37 C38 1.4973(19) . ?
C37 H28 0.9800 . ?
C37 H29 0.9800 . ?
C37 H30 0.9800 . ?
C38 O9 1.2136(19) . ?
C38 O10 1.3233(18) . ?
O10 C39 1.4587(18) . ?
C39 C40 1.508(2) . ?
C39 H31 0.9900 . ?
C39 H32 0.9900 . ?
C40 H33 0.9800 . ?
C40 H34 0.9800 . ?
C40 H35 0.9800 . ?
F2 B2 1.4145(18) . ?

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
N1 C1 C2 108.76(13) . . ?
N1 C1 H1 125.6 . . ?
C2 C1 H1 125.6 . . ?
C1 C2 C3 107.08(13) . . ?
C1 C2 H2 126.5 . . ?
C3 C2 H2 126.5 . . ?
C4 C3 C2 107.62(13) . . ?
C4 C3 H3 126.2 . . ?
C2 C3 H3 126.2 . . ?
N1 C4 C3 107.17(12) . . ?
N1 C4 C5 121.41(12) . . ?
C3 C4 C5 131.42(13) . . ?
C1 N1 C4 109.37(12) . . ?
C1 N1 H4 125.3 . . ?
C4 N1 H4 125.3 . . ?
O1 C5 C6 121.83(12) . . ?
O1 C5 C4 114.92(12) . . ?
C6 C5 C4 123.25(12) . . ?
C5 C6 C7 119.40(13) . . ?
C5 C6 H5 120.3 . . ?
C7 C6 H5 120.3 . . ?
O2 C7 C6 121.57(12) . . ?
O2 C7 C8 114.80(12) . . ?
C6 C7 C8 123.59(13) . . ?
N2 C8 C9 107.41(12) . . ?
N2 C8 C7 120.33(13) . . ?
C9 C8 C7 132.25(13) . . ?
C8 C9 C10 107.31(14) . . ?
C8 C9 H6 126.3 . . ?
C10 C9 H6 126.3 . . ?
C11 C10 C9 107.37(13) . . ?
C11 C10 H7 126.3 . . ?
C9 C10 H7 126.3 . . ?
N2 C11 C10 108.71(13) . . ?
N2 C11 H8 125.6 . . ?
C10 C11 H8 125.6 . . ?
C11 N2 C8 109.19(13) . . ?
C11 N2 H9 125.4 . . ?
C8 N2 H9 125.4 . . ?
C5 O1 B1 122.88(11) . . ?
C7 O2 B1 123.14(11) . . ?
F1 B1 O1 107.54(11) . . ?
F1 B1 O2 106.13(11) . . ?
O1 B1 O2 110.14(11) . . ?
F1 B1 C12 112.85(12) . . ?
O1 B1 C12 110.86(11) . . ?
O2 B1 C12 109.20(11) . . ?
C17 C12 C13 116.82(13) . . ?
C17 C12 B1 121.26(12) . . ?
C13 C12 B1 121.62(12) . . ?
C14 C13 C12 121.42(13) . . ?
C14 C13 H10 119.3 . . ?
C12 C13 H10 119.3 . . ?
C15 C14 C13 120.37(13) . . ?
C15 C14 C18 120.23(13) . . ?
C13 C14 C18 119.34(12) . . ?
C16 C15 C14 118.91(14) . . ?
C16 C15 H11 120.5 . . ?
C14 C15 H11 120.5 . . ?
C17 C16 C15 120.29(13) . . ?
C17 C16 H12 119.9 . . ?
C15 C16 H12 119.9 . . ?
C16 C17 C12 122.17(13) . . ?
C16 C17 H13 118.9 . . ?
C12 C17 H13 118.9 . . ?
O3 C18 O4 123.08(13) . . ?
O3 C18 C14 122.63(13) . . ?
O4 C18 C14 114.28(12) . . ?
C18 O4 H14 109.5 . . ?
N3 C19 C20 108.78(12) . . ?
N3 C19 H15 125.6 . . ?
C20 C19 H15 125.6 . . ?
C19 C20 C21 107.49(13) . . ?
C19 C20 H16 126.3 . . ?
C21 C20 H16 126.3 . . ?
C22 C21 C20 107.13(13) . . ?
C22 C21 H17 126.4 . . ?
C20 C21 H17 126.4 . . ?
N3 C22 C21 107.38(12) . . ?
N3 C22 C23 121.05(12) . . ?
C21 C22 C23 131.49(13) . . ?
C19 N3 C22 109.21(12) . . ?
C19 N3 H36 125.4 . . ?
C22 N3 H36 125.4 . . ?
O5 C23 C24 121.66(12) . . ?
O5 C23 C22 115.54(12) . . ?
C24 C23 C22 122.80(13) . . ?
C25 C24 C23 119.15(13) . . ?
C25 C24 H18 120.4 . . ?
C23 C24 H18 120.4 . . ?
O6 C25 C24 121.70(12) . . ?
O6 C25 C26 114.77(12) . . ?
C24 C25 C26 123.52(13) . . ?
C23 O5 B2 120.50(11) . . ?
C25 O6 B2 120.54(11) . . ?
N4 C26 C27 107.44(12) . . ?
N4 C26 C25 120.56(13) . . ?
C27 C26 C25 131.79(13) . . ?
C26 C27 C28 107.31(13) . . ?
C26 C27 H19 126.3 . . ?
C28 C27 H19 126.3 . . ?
C29 C28 C27 107.24(14) . . ?
C29 C28 H20 126.4 . . ?
C27 C28 H20 126.4 . . ?
N4 C29 C28 108.71(13) . . ?
N4 C29 H21 125.6 . . ?
C28 C29 H21 125.6 . . ?
C29 N4 C26 109.30(12) . . ?
C29 N4 H22 125.3 . . ?
C26 N4 H22 125.3 . . ?
C31 C30 C35 116.80(13) . . ?
C31 C30 B2 122.02(12) . . ?
C35 C30 B2 121.11(12) . . ?
C32 C31 C30 121.92(12) . . ?
C32 C31 H23 119.0 . . ?
C30 C31 H23 119.0 . . ?
C31 C32 C33 120.14(13) . . ?
C31 C32 C36 118.77(12) . . ?
C33 C32 C36 121.09(13) . . ?
C34 C33 C32 118.82(14) . . ?
C34 C33 H24 120.6 . . ?
C32 C33 H24 120.6 . . ?
C35 C34 C33 120.30(13) . . ?
C35 C34 H25 119.9 . . ?
C33 C34 H25 119.9 . . ?
C34 C35 C30 122.00(13) . . ?
C34 C35 H26 119.0 . . ?
C30 C35 H26 119.0 . . ?
O7 C36 O8 122.95(13) . . ?
O7 C36 C32 121.80(13) . . ?
O8 C36 C32 115.24(12) . . ?
C36 O8 H27 109.5 . . ?
C38 C37 H28 109.5 . . ?
C38 C37 H29 109.5 . . ?
H28 C37 H29 109.5 . . ?
C38 C37 H30 109.5 . . ?
H28 C37 H30 109.5 . . ?
H29 C37 H30 109.5 . . ?
O9 C38 O10 123.61(13) . . ?
O9 C38 C37 124.95(14) . . ?
O10 C38 C37 111.44(13) . . ?
C38 O10 C39 117.14(12) . . ?
O10 C39 C40 105.39(13) . . ?
O10 C39 H31 110.7 . . ?
C40 C39 H31 110.7 . . ?
O10 C39 H32 110.7 . . ?
C40 C39 H32 110.7 . . ?
H31 C39 H32 108.8 . . ?
C39 C40 H33 109.5 . . ?
C39 C40 H34 109.5 . . ?
H33 C40 H34 109.5 . . ?
C39 C40 H35 109.5 . . ?
H33 C40 H35 109.5 . . ?
H34 C40 H35 109.5 . . ?
F2 B2 O6 107.83(12) . . ?
F2 B2 O5 105.89(11) . . ?
O6 B2 O5 110.05(11) . . ?
F2 B2 C30 112.71(11) . . ?
O6 B2 C30 110.27(11) . . ?
O5 B2 C30 109.98(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.93(17) . . . . ?
C1 C2 C3 C4 -0.66(17) . . . . ?
C2 C3 C4 N1 0.16(16) . . . . ?
C2 C3 C4 C5 179.50(14) . . . . ?
C2 C1 N1 C4 -0.85(17) . . . . ?
C3 C4 N1 C1 0.42(16) . . . . ?
C5 C4 N1 C1 -179.00(12) . . . . ?
N1 C4 C5 O1 -5.68(19) . . . . ?
C3 C4 C5 O1 175.06(14) . . . . ?
N1 C4 C5 C6 174.92(13) . . . . ?
C3 C4 C5 C6 -4.3(2) . . . . ?
O1 C5 C6 C7 -1.8(2) . . . . ?
C4 C5 C6 C7 177.58(12) . . . . ?
C5 C6 C7 O2 0.2(2) . . . . ?
C5 C6 C7 C8 -177.56(12) . . . . ?
O2 C7 C8 N2 3.39(19) . . . . ?
C6 C7 C8 N2 -178.68(13) . . . . ?
O2 C7 C8 C9 -176.74(14) . . . . ?
C6 C7 C8 C9 1.2(2) . . . . ?
N2 C8 C9 C10 0.20(17) . . . . ?
C7 C8 C9 C10 -179.69(15) . . . . ?
C8 C9 C10 C11 0.02(18) . . . . ?
C9 C10 C11 N2 -0.23(19) . . . . ?
C10 C11 N2 C8 0.36(18) . . . . ?
C9 C8 N2 C11 -0.35(17) . . . . ?
C7 C8 N2 C11 179.56(13) . . . . ?
C6 C5 O1 B1 -4.2(2) . . . . ?
C4 C5 O1 B1 176.36(12) . . . . ?
C6 C7 O2 B1 7.3(2) . . . . ?
C8 C7 O2 B1 -174.75(12) . . . . ?
C5 O1 B1 F1 -105.05(14) . . . . ?
C5 O1 B1 O2 10.19(18) . . . . ?
C5 O1 B1 C12 131.16(12) . . . . ?
C7 O2 B1 F1 104.38(13) . . . . ?
C7 O2 B1 O1 -11.74(18) . . . . ?
C7 O2 B1 C12 -133.70(12) . . . . ?
F1 B1 C12 C17 -154.65(12) . . . . ?
O1 B1 C12 C17 -33.94(17) . . . . ?
O2 B1 C12 C17 87.58(15) . . . . ?
F1 B1 C12 C13 31.79(17) . . . . ?
O1 B1 C12 C13 152.49(12) . . . . ?
O2 B1 C12 C13 -85.98(15) . . . . ?
C17 C12 C13 C14 -1.18(19) . . . . ?
B1 C12 C13 C14 172.66(12) . . . . ?
C12 C13 C14 C15 1.0(2) . . . . ?
C12 C13 C14 C18 -176.43(12) . . . . ?
C13 C14 C15 C16 0.0(2) . . . . ?
C18 C14 C15 C16 177.42(13) . . . . ?
C14 C15 C16 C17 -0.8(2) . . . . ?
C15 C16 C17 C12 0.6(2) . . . . ?
C13 C12 C17 C16 0.4(2) . . . . ?
B1 C12 C17 C16 -173.50(13) . . . . ?
C15 C14 C18 O3 -176.81(13) . . . . ?
C13 C14 C18 O3 0.7(2) . . . . ?
C15 C14 C18 O4 2.5(2) . . . . ?
C13 C14 C18 O4 179.97(12) . . . . ?
N3 C19 C20 C21 0.39(17) . . . . ?
C19 C20 C21 C22 -0.03(17) . . . . ?
C20 C21 C22 N3 -0.33(16) . . . . ?
C20 C21 C22 C23 176.23(14) . . . . ?
C20 C19 N3 C22 -0.61(16) . . . . ?
C21 C22 N3 C19 0.58(15) . . . . ?
C23 C22 N3 C19 -176.41(12) . . . . ?
N3 C22 C23 O5 -6.52(18) . . . . ?
C21 C22 C23 O5 177.31(14) . . . . ?
N3 C22 C23 C24 173.09(13) . . . . ?
C21 C22 C23 C24 -3.1(2) . . . . ?
O5 C23 C24 C25 -2.3(2) . . . . ?
C22 C23 C24 C25 178.15(13) . . . . ?
C23 C24 C25 O6 1.9(2) . . . . ?
C23 C24 C25 C26 -178.57(13) . . . . ?
C24 C23 O5 B2 -13.89(19) . . . . ?
C22 C23 O5 B2 165.73(11) . . . . ?
C24 C25 O6 B2 14.60(19) . . . . ?
C26 C25 O6 B2 -164.92(12) . . . . ?
O6 C25 C26 N4 2.72(19) . . . . ?
C24 C25 C26 N4 -176.79(13) . . . . ?
O6 C25 C26 C27 176.67(14) . . . . ?
C24 C25 C26 C27 -2.8(2) . . . . ?
N4 C26 C27 C28 0.57(16) . . . . ?
C25 C26 C27 C28 -173.97(15) . . . . ?
C26 C27 C28 C29 -0.78(18) . . . . ?
C27 C28 C29 N4 0.70(18) . . . . ?
C28 C29 N4 C26 -0.35(18) . . . . ?
C27 C26 N4 C29 -0.15(16) . . . . ?
C25 C26 N4 C29 175.13(13) . . . . ?
C35 C30 C31 C32 -1.7(2) . . . . ?
B2 C30 C31 C32 175.24(12) . . . . ?
C30 C31 C32 C33 0.8(2) . . . . ?
C30 C31 C32 C36 -178.90(12) . . . . ?
C31 C32 C33 C34 0.6(2) . . . . ?
C36 C32 C33 C34 -179.69(14) . . . . ?
C32 C33 C34 C35 -1.1(2) . . . . ?
C33 C34 C35 C30 0.1(3) . . . . ?
C31 C30 C35 C34 1.3(2) . . . . ?
B2 C30 C35 C34 -175.70(14) . . . . ?
C31 C32 C36 O7 -2.0(2) . . . . ?
C33 C32 C36 O7 178.28(13) . . . . ?
C31 C32 C36 O8 177.00(12) . . . . ?
C33 C32 C36 O8 -2.68(19) . . . . ?
O9 C38 O10 C39 -0.3(2) . . . . ?
C37 C38 O10 C39 179.90(12) . . . . ?
C38 O10 C39 C40 171.50(13) . . . . ?
C25 O6 B2 F2 87.48(14) . . . . ?
C25 O6 B2 O5 -27.58(17) . . . . ?
C25 O6 B2 C30 -149.08(12) . . . . ?
C23 O5 B2 F2 -89.02(14) . . . . ?
C23 O5 B2 O6 27.25(17) . . . . ?
C23 O5 B2 C30 148.93(11) . . . . ?
C31 C30 B2 F2 146.23(13) . . . . ?
C35 C30 B2 F2 -36.95(18) . . . . ?
C31 C30 B2 O6 25.67(18) . . . . ?
C35 C30 B2 O6 -157.52(13) . . . . ?
C31 C30 B2 O5 -95.87(15) . . . . ?
C35 C30 B2 O5 80.94(16) . . . . ?

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
N1 H4 F2 0.88 2.03 2.7869(15) 144.2 2_656
N2 H9 O9 0.88 2.06 2.9174(17) 162.9 .
O4 H14 O7 0.84 1.79 2.6143(15) 167.0 .
C21 H17 O7 0.95 2.62 3.545(2) 163.7 2_766
N4 H22 F1 0.88 2.04 2.7528(15) 137.8 2_656
O8 H27 O3 0.84 1.80 2.6281(14) 168.9 .
N1 H4 F2 0.88 2.03 2.7869(15) 144.2 2_656
N2 H9 O9 0.88 2.06 2.9174(17) 162.9 .
N3 H36 O9 0.88 2.10 2.9429(17) 159.4 2_666
C19 H15 F1 0.95 2.63 3.4618(17) 146.8 2_666

_refine_diff_density_max         0.612
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.048



####################################################################### 
# 
# 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_ydkr_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2086729'
loop_
_audit_author_name
_audit_author_address
'Nobuhiro Yasuda'
;Japan Synchrotron Radiation Research Institute
Japan
;
_audit_update_record             
;
2021-05-29 deposited with the CCDC.	2021-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C18 H13 B F N2 O4, C16 H36 N'
_chemical_formula_sum            'C34 H49 B F N3 O4'
_chemical_formula_weight         593.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0041 0.0020 '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 0.0021 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0215 0.0127 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0078 0.0041 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0135 0.0075 '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'

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

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

_cell_length_a                   12.2597(5)
_cell_length_b                   18.3041(7)
_cell_length_c                   15.1300(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.384(3)
_cell_angle_gamma                90
_cell_volume                     3395.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    27739
_cell_measurement_theta_min      1.921
_cell_measurement_theta_max      27.955

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'ABSCOR (T.Higashi, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.78201
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'synchrotron radiation SPring-8 BL40XU'
_diffrn_radiation_monochromator  'Si(111) Channel Cut'
_diffrn_measurement_device_type  'Rigaku Saturn 724'
_diffrn_measurement_method       'Oscillation Photograph'
_diffrn_detector_area_resol_mean 29
_diffrn_reflns_number            27739
_diffrn_reflns_av_unetI/netI     0.0754
_diffrn_reflns_av_R_equivalents  0.0841
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.921
_diffrn_reflns_theta_max         27.955
_diffrn_reflns_theta_full        27.955
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6114
_reflns_number_gt                3707
_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       'Rapid Auto(Rigaku)'
_computing_cell_refinement       'Rapid Auto(Rigaku)'
_computing_data_reduction        'Rapid Auto(Rigaku)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1239P)²+0.4339P] 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         6114
_refine_ls_number_parameters     403
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1254
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.2276
_refine_ls_wR_factor_gt          0.1741
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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
C1 C 0.2751(3) 0.25670(18) 0.9708(2) 0.0426(8) Uani 1 1 d . . . . .
H1 H 0.2082 0.2509 1.0014 0.051 Uiso 1 1 calc R U . . .
C35 C 0.8978(13) -0.0522(9) 0.5137(11) 0.073(5) Uani 0.282(8) 1 d . . P A 2
H49 H 0.9514 -0.0221 0.4826 0.109 Uiso 0.282(8) 1 calc R U P A 2
H50 H 0.8888 -0.0988 0.4826 0.109 Uiso 0.282(8) 1 calc R U P A 2
H51 H 0.9233 -0.0613 0.5742 0.109 Uiso 0.282(8) 1 calc R U P A 2
C2 C 0.3721(3) 0.22073(18) 0.9910(2) 0.0420(8) Uani 1 1 d . . . . .
H2 H 0.3841 0.1869 1.0377 0.050 Uiso 1 1 calc R U . . .
C3 C 0.4488(3) 0.24426(18) 0.9288(2) 0.0393(8) Uani 1 1 d . . . . .
H3 H 0.5226 0.2288 0.9252 0.047 Uiso 1 1 calc R U . . .
C4 C 0.3978(2) 0.29391(17) 0.87347(18) 0.0325(7) Uani 1 1 d . . . . .
C5 C 0.4429(2) 0.33497(17) 0.80205(19) 0.0334(7) Uani 1 1 d . . . . .
C6 C 0.3875(2) 0.38702(16) 0.75251(19) 0.0333(7) Uani 1 1 d . . . . .
H4 H 0.3106 0.3916 0.7578 0.040 Uiso 1 1 calc R U . . .
C7 C 0.4434(2) 0.43205(16) 0.69583(19) 0.0308(7) Uani 1 1 d . . . . .
C8 C 0.3973(2) 0.49201(16) 0.64852(19) 0.0323(7) Uani 1 1 d . . . . .
C9 C 0.4452(3) 0.53926(16) 0.58769(19) 0.0347(7) Uani 1 1 d . . . . .
H5 H 0.5194 0.5390 0.5701 0.042 Uiso 1 1 calc R U . . .
C10 C 0.3643(3) 0.58719(18) 0.5572(2) 0.0407(8) Uani 1 1 d . . . . .
H6 H 0.3729 0.6249 0.5147 0.049 Uiso 1 1 calc R U . . .
C11 C 0.2693(3) 0.56901(18) 0.6011(2) 0.0412(8) Uani 1 1 d . . . . .
H7 H 0.2010 0.5928 0.5937 0.049 Uiso 1 1 calc R U . . .
C12 C 0.8870(3) 0.35966(18) 0.8322(2) 0.0376(8) Uani 1 1 d . . . . .
H8 H 0.9170 0.3450 0.8875 0.045 Uiso 1 1 calc R U . . .
C13 C 0.7764(3) 0.34756(16) 0.8136(2) 0.0346(7) Uani 1 1 d . . . . .
H9 H 0.7319 0.3259 0.8576 0.042 Uiso 1 1 calc R U . . .
C14 C 0.7293(2) 0.36634(16) 0.73223(19) 0.0301(7) Uani 1 1 d . . . . .
C15 C 0.7986(2) 0.39902(17) 0.6701(2) 0.0349(7) Uani 1 1 d . . . . .
H10 H 0.7699 0.4122 0.6138 0.042 Uiso 1 1 calc R U . . .
C16 C 0.9079(3) 0.41258(18) 0.6885(2) 0.0384(8) Uani 1 1 d . . . . .
H11 H 0.9522 0.4354 0.6452 0.046 Uiso 1 1 calc R U . . .
C17 C 0.9529(2) 0.39325(18) 0.7693(2) 0.0387(8) Uani 1 1 d . . . . .
C18 C 1.0736(3) 0.4070(2) 0.7893(3) 0.0477(9) Uani 1 1 d . . . . .
C19 C 0.6575(3) 0.14486(18) 0.6953(2) 0.0382(8) Uani 1 1 d . . . . .
H14 H 0.6566 0.1579 0.6318 0.046 Uiso 1 1 calc R U . . .
H15 H 0.6505 0.1908 0.7293 0.046 Uiso 1 1 calc R U . . .
C20 C 0.5582(3) 0.0977(2) 0.7139(3) 0.0553(10) Uani 1 1 d . . . . .
H16 H 0.5537 0.0885 0.7783 0.066 Uiso 1 1 calc R U . . .
H17 H 0.5666 0.0500 0.6839 0.066 Uiso 1 1 calc R U . . .
C21 C 0.4524(3) 0.1341(2) 0.6821(2) 0.0468(9) Uani 1 1 d . . . . .
H18 H 0.3898 0.1060 0.7052 0.056 Uiso 1 1 calc R U . . .
H19 H 0.4485 0.1839 0.7076 0.056 Uiso 1 1 calc R U . . .
C22 C 0.4411(3) 0.1398(3) 0.5835(3) 0.0726(13) Uani 1 1 d . . . . .
H40 H 0.4931 0.1760 0.5612 0.109 Uiso 1 1 calc R U . . .
H41 H 0.3667 0.1550 0.5682 0.109 Uiso 1 1 calc R U . . .
H42 H 0.4563 0.0922 0.5567 0.109 Uiso 1 1 calc R U . . .
C23 C 0.8532(2) 0.16944(17) 0.6992(2) 0.0344(7) Uani 1 1 d . . . . .
H20 H 0.8471 0.1841 0.6363 0.041 Uiso 1 1 calc R U . . .
H21 H 0.8357 0.2129 0.7354 0.041 Uiso 1 1 calc R U . . .
C24 C 0.9703(3) 0.14803(18) 0.7177(2) 0.0432(8) Uani 1 1 d . . . . .
H22 H 0.9787 0.1351 0.7810 0.052 Uiso 1 1 calc R U . . .
H23 H 0.9892 0.1045 0.6822 0.052 Uiso 1 1 calc R U . . .
C25 C 1.0467(3) 0.2095(2) 0.6956(3) 0.0527(10) Uani 1 1 d . . . . .
H24 H 1.0410 0.2194 0.6314 0.063 Uiso 1 1 calc R U . . .
H25 H 1.0220 0.2540 0.7269 0.063 Uiso 1 1 calc R U . . .
C26 C 1.1645(3) 0.1967(2) 0.7183(3) 0.0579(10) Uani 1 1 d . . . . .
H43 H 1.1720 0.1882 0.7820 0.087 Uiso 1 1 calc R U . . .
H44 H 1.2075 0.2396 0.7017 0.087 Uiso 1 1 calc R U . . .
H45 H 1.1910 0.1538 0.6861 0.087 Uiso 1 1 calc R U . . .
C27 C 0.7717(3) 0.08573(17) 0.81279(19) 0.0355(7) Uani 1 1 d . . . . .
H26 H 0.7120 0.0502 0.8221 0.043 Uiso 1 1 calc R U . . .
H27 H 0.8414 0.0595 0.8225 0.043 Uiso 1 1 calc R U . . .
C28 C 0.7625(3) 0.14523(18) 0.8821(2) 0.0395(8) Uani 1 1 d . . . . .
H28 H 0.7041 0.1799 0.8649 0.047 Uiso 1 1 calc R U . . .
H29 H 0.8320 0.1727 0.8859 0.047 Uiso 1 1 calc R U . . .
C29 C 0.7367(3) 0.11210(19) 0.9717(2) 0.0449(9) Uani 1 1 d . . . . .
H30 H 0.6643 0.0882 0.9685 0.054 Uiso 1 1 calc R U . . .
H31 H 0.7915 0.0740 0.9855 0.054 Uiso 1 1 calc R U . . .
C30 C 0.7362(4) 0.1679(2) 1.0455(2) 0.0600(11) Uani 1 1 d . . . . .
H46 H 0.8097 0.1881 1.0532 0.090 Uiso 1 1 calc R U . . .
H47 H 0.7133 0.1444 1.1006 0.090 Uiso 1 1 calc R U . . .
H48 H 0.6852 0.2074 1.0306 0.090 Uiso 1 1 calc R U . . .
C31 C 0.7878(3) 0.04311(17) 0.6611(2) 0.0382(8) Uani 1 1 d . . . . .
H32 H 0.8580 0.0212 0.6801 0.046 Uiso 1 1 calc R U . . .
H33 H 0.7297 0.0071 0.6739 0.046 Uiso 1 1 calc R U . . .
C32 C 0.7914(3) 0.05473(18) 0.5621(2) 0.0492(9) Uani 1 1 d . . . . .
H34 H 0.8524 0.0879 0.5472 0.059 Uiso 1 1 calc R U . . .
H35 H 0.7226 0.0776 0.5416 0.059 Uiso 1 1 calc R U . . .
C33 C 0.8071(4) -0.0190(2) 0.5158(3) 0.0653(12) Uani 1 1 d . . . . .
H36 H 0.8701 -0.0444 0.5431 0.078 Uiso 0.718(8) 1 calc R U P A 1
H37 H 0.7416 -0.0494 0.5257 0.078 Uiso 0.718(8) 1 calc R U P A 1
H38 H 0.7541 -0.0531 0.5425 0.078 Uiso 0.282(8) 1 calc R U P A 2
H39 H 0.7839 -0.0120 0.4535 0.078 Uiso 0.282(8) 1 calc R U P A 2
C34 C 0.8254(5) -0.0131(3) 0.4207(3) 0.0608(19) Uani 0.718(8) 1 d . . P A 1
H52 H 0.7620 0.0099 0.3925 0.091 Uiso 0.718(8) 1 calc R U P A 1
H53 H 0.8362 -0.0619 0.3958 0.091 Uiso 0.718(8) 1 calc R U P A 1
H54 H 0.8904 0.0168 0.4101 0.091 Uiso 0.718(8) 1 calc R U P A 1
N1 N 0.2911(2) 0.30125(14) 0.90078(16) 0.0367(7) Uani 1 1 d . . . . .
H12 H 0.2418 0.3301 0.8767 0.044 Uiso 1 1 calc R U . . .
N2 N 0.2887(2) 0.51224(14) 0.65592(16) 0.0377(7) Uani 1 1 d . . . . .
H13 H 0.2405 0.4915 0.6906 0.045 Uiso 1 1 calc R U . . .
N3 N 0.7674(2) 0.11091(13) 0.71714(16) 0.0339(6) Uani 1 1 d . . . . .
O1 O 0.54777(17) 0.32144(11) 0.78794(13) 0.0349(5) Uani 1 1 d . . . . .
O2 O 0.55098(16) 0.42437(11) 0.68464(13) 0.0339(5) Uani 1 1 d . . . . .
B1 B 0.6041(3) 0.3538(2) 0.7096(2) 0.0321(8) Uani 1 1 d . . . . .
F1 F 0.58735(14) 0.30568(9) 0.63685(11) 0.0390(5) Uani 1 1 d . . . . .
O3 O 1.1135(2) 0.37754(16) 0.85640(18) 0.0624(8) Uani 1 1 d . . . . .
O4 O 1.1226(2) 0.44640(16) 0.73418(19) 0.0656(8) 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
C1 N1 1.352(4) . ?
C1 C2 1.392(5) . ?
C1 H1 0.9500 . ?
C35 C33 1.268(15) . ?
C35 H49 0.9800 . ?
C35 H50 0.9800 . ?
C35 H51 0.9800 . ?
C2 C3 1.402(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(4) . ?
C3 H3 0.9500 . ?
C4 N1 1.381(4) . ?
C4 C5 1.430(4) . ?
C5 O1 1.328(4) . ?
C5 C6 1.387(4) . ?
C6 C7 1.376(4) . ?
C6 H4 0.9500 . ?
C7 O2 1.339(3) . ?
C7 C8 1.425(4) . ?
C8 N2 1.387(4) . ?
C8 C9 1.395(4) . ?
C9 C10 1.400(4) . ?
C9 H5 0.9500 . ?
C10 C11 1.385(5) . ?
C10 H6 0.9500 . ?
C11 N2 1.350(4) . ?
C11 H7 0.9500 . ?
C12 C17 1.396(5) . ?
C12 C13 1.400(4) . ?
C12 H8 0.9500 . ?
C13 C14 1.399(4) . ?
C13 H9 0.9500 . ?
C14 C15 1.405(4) . ?
C14 B1 1.588(5) . ?
C15 C16 1.389(4) . ?
C15 H10 0.9500 . ?
C16 C17 1.384(4) . ?
C16 H11 0.9500 . ?
C17 C18 1.528(5) . ?
C18 O3 1.247(4) . ?
C18 O4 1.258(4) . ?
C19 N3 1.518(4) . ?
C19 C20 1.520(5) . ?
C19 H14 0.9900 . ?
C19 H15 0.9900 . ?
C20 C21 1.533(5) . ?
C20 H16 0.9900 . ?
C20 H17 0.9900 . ?
C21 C22 1.501(5) . ?
C21 H18 0.9900 . ?
C21 H19 0.9900 . ?
C22 H40 0.9800 . ?
C22 H41 0.9800 . ?
C22 H42 0.9800 . ?
C23 C24 1.513(4) . ?
C23 N3 1.527(4) . ?
C23 H20 0.9900 . ?
C23 H21 0.9900 . ?
C24 C25 1.504(5) . ?
C24 H22 0.9900 . ?
C24 H23 0.9900 . ?
C25 C26 1.501(5) . ?
C25 H24 0.9900 . ?
C25 H25 0.9900 . ?
C26 H43 0.9800 . ?
C26 H44 0.9800 . ?
C26 H45 0.9800 . ?
C27 C28 1.517(4) . ?
C27 N3 1.520(4) . ?
C27 H26 0.9900 . ?
C27 H27 0.9900 . ?
C28 C29 1.520(4) . ?
C28 H28 0.9900 . ?
C28 H29 0.9900 . ?
C29 C30 1.514(5) . ?
C29 H30 0.9900 . ?
C29 H31 0.9900 . ?
C30 H46 0.9800 . ?
C30 H47 0.9800 . ?
C30 H48 0.9800 . ?
C31 C32 1.514(4) . ?
C31 N3 1.524(4) . ?
C31 H32 0.9900 . ?
C31 H33 0.9900 . ?
C32 C33 1.533(5) . ?
C32 H34 0.9900 . ?
C32 H35 0.9900 . ?
C33 C34 1.461(6) . ?
C33 H36 0.9900 . ?
C33 H37 0.9900 . ?
C33 H38 0.9900 . ?
C33 H39 0.9900 . ?
C34 H52 0.9800 . ?
C34 H53 0.9800 . ?
C34 H54 0.9800 . ?
N1 H12 0.8800 . ?
N2 H13 0.8800 . ?
O1 B1 1.498(4) . ?
O2 B1 1.493(4) . ?
B1 F1 1.424(4) . ?

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
N1 C1 C2 109.2(3) . . ?
N1 C1 H1 125.4 . . ?
C2 C1 H1 125.4 . . ?
C33 C35 H49 109.5 . . ?
C33 C35 H50 109.5 . . ?
H49 C35 H50 109.5 . . ?
C33 C35 H51 109.5 . . ?
H49 C35 H51 109.5 . . ?
H50 C35 H51 109.5 . . ?
C1 C2 C3 106.4(3) . . ?
C1 C2 H2 126.8 . . ?
C3 C2 H2 126.8 . . ?
C4 C3 C2 107.8(3) . . ?
C4 C3 H3 126.1 . . ?
C2 C3 H3 126.1 . . ?
N1 C4 C3 107.9(3) . . ?
N1 C4 C5 123.1(3) . . ?
C3 C4 C5 128.9(3) . . ?
O1 C5 C6 120.8(3) . . ?
O1 C5 C4 113.8(3) . . ?
C6 C5 C4 125.4(3) . . ?
C7 C6 C5 120.3(3) . . ?
C7 C6 H4 119.9 . . ?
C5 C6 H4 119.9 . . ?
O2 C7 C6 120.8(3) . . ?
O2 C7 C8 113.9(3) . . ?
C6 C7 C8 125.3(3) . . ?
N2 C8 C9 107.2(3) . . ?
N2 C8 C7 122.8(3) . . ?
C9 C8 C7 129.9(3) . . ?
C8 C9 C10 107.8(3) . . ?
C8 C9 H5 126.1 . . ?
C10 C9 H5 126.1 . . ?
C11 C10 C9 106.7(3) . . ?
C11 C10 H6 126.6 . . ?
C9 C10 H6 126.6 . . ?
N2 C11 C10 109.5(3) . . ?
N2 C11 H7 125.2 . . ?
C10 C11 H7 125.2 . . ?
C17 C12 C13 119.8(3) . . ?
C17 C12 H8 120.1 . . ?
C13 C12 H8 120.1 . . ?
C14 C13 C12 122.1(3) . . ?
C14 C13 H9 119.0 . . ?
C12 C13 H9 119.0 . . ?
C13 C14 C15 116.5(3) . . ?
C13 C14 B1 123.1(3) . . ?
C15 C14 B1 120.3(3) . . ?
C16 C15 C14 121.9(3) . . ?
C16 C15 H10 119.1 . . ?
C14 C15 H10 119.1 . . ?
C17 C16 C15 120.7(3) . . ?
C17 C16 H11 119.7 . . ?
C15 C16 H11 119.7 . . ?
C16 C17 C12 119.0(3) . . ?
C16 C17 C18 120.8(3) . . ?
C12 C17 C18 120.1(3) . . ?
O3 C18 O4 127.0(3) . . ?
O3 C18 C17 117.6(3) . . ?
O4 C18 C17 115.4(3) . . ?
N3 C19 C20 116.0(3) . . ?
N3 C19 H14 108.3 . . ?
C20 C19 H14 108.3 . . ?
N3 C19 H15 108.3 . . ?
C20 C19 H15 108.3 . . ?
H14 C19 H15 107.4 . . ?
C19 C20 C21 111.8(3) . . ?
C19 C20 H16 109.2 . . ?
C21 C20 H16 109.2 . . ?
C19 C20 H17 109.2 . . ?
C21 C20 H17 109.2 . . ?
H16 C20 H17 107.9 . . ?
C22 C21 C20 114.5(3) . . ?
C22 C21 H18 108.6 . . ?
C20 C21 H18 108.6 . . ?
C22 C21 H19 108.6 . . ?
C20 C21 H19 108.6 . . ?
H18 C21 H19 107.6 . . ?
C21 C22 H40 109.5 . . ?
C21 C22 H41 109.5 . . ?
H40 C22 H41 109.5 . . ?
C21 C22 H42 109.5 . . ?
H40 C22 H42 109.5 . . ?
H41 C22 H42 109.5 . . ?
C24 C23 N3 116.0(3) . . ?
C24 C23 H20 108.3 . . ?
N3 C23 H20 108.3 . . ?
C24 C23 H21 108.3 . . ?
N3 C23 H21 108.3 . . ?
H20 C23 H21 107.4 . . ?
C25 C24 C23 110.9(3) . . ?
C25 C24 H22 109.5 . . ?
C23 C24 H22 109.5 . . ?
C25 C24 H23 109.5 . . ?
C23 C24 H23 109.5 . . ?
H22 C24 H23 108.1 . . ?
C26 C25 C24 115.6(3) . . ?
C26 C25 H24 108.4 . . ?
C24 C25 H24 108.4 . . ?
C26 C25 H25 108.4 . . ?
C24 C25 H25 108.4 . . ?
H24 C25 H25 107.5 . . ?
C25 C26 H43 109.5 . . ?
C25 C26 H44 109.5 . . ?
H43 C26 H44 109.5 . . ?
C25 C26 H45 109.5 . . ?
H43 C26 H45 109.5 . . ?
H44 C26 H45 109.5 . . ?
C28 C27 N3 116.0(2) . . ?
C28 C27 H26 108.3 . . ?
N3 C27 H26 108.3 . . ?
C28 C27 H27 108.3 . . ?
N3 C27 H27 108.3 . . ?
H26 C27 H27 107.4 . . ?
C27 C28 C29 110.3(3) . . ?
C27 C28 H28 109.6 . . ?
C29 C28 H28 109.6 . . ?
C27 C28 H29 109.6 . . ?
C29 C28 H29 109.6 . . ?
H28 C28 H29 108.1 . . ?
C30 C29 C28 113.0(3) . . ?
C30 C29 H30 109.0 . . ?
C28 C29 H30 109.0 . . ?
C30 C29 H31 109.0 . . ?
C28 C29 H31 109.0 . . ?
H30 C29 H31 107.8 . . ?
C29 C30 H46 109.5 . . ?
C29 C30 H47 109.5 . . ?
H46 C30 H47 109.5 . . ?
C29 C30 H48 109.5 . . ?
H46 C30 H48 109.5 . . ?
H47 C30 H48 109.5 . . ?
C32 C31 N3 116.2(3) . . ?
C32 C31 H32 108.2 . . ?
N3 C31 H32 108.2 . . ?
C32 C31 H33 108.2 . . ?
N3 C31 H33 108.2 . . ?
H32 C31 H33 107.4 . . ?
C31 C32 C33 109.5(3) . . ?
C31 C32 H34 109.8 . . ?
C33 C32 H34 109.8 . . ?
C31 C32 H35 109.8 . . ?
C33 C32 H35 109.8 . . ?
H34 C32 H35 108.2 . . ?
C35 C33 C32 123.1(9) . . ?
C34 C33 C32 113.9(4) . . ?
C34 C33 H36 108.8 . . ?
C32 C33 H36 108.8 . . ?
C34 C33 H37 108.8 . . ?
C32 C33 H37 108.8 . . ?
H36 C33 H37 107.7 . . ?
C35 C33 H38 106.6 . . ?
C32 C33 H38 106.6 . . ?
C35 C33 H39 106.6 . . ?
C32 C33 H39 106.6 . . ?
H38 C33 H39 106.5 . . ?
C33 C34 H52 109.5 . . ?
C33 C34 H53 109.5 . . ?
H52 C34 H53 109.5 . . ?
C33 C34 H54 109.5 . . ?
H52 C34 H54 109.5 . . ?
H53 C34 H54 109.5 . . ?
C1 N1 C4 108.6(3) . . ?
C1 N1 H12 125.7 . . ?
C4 N1 H12 125.7 . . ?
C11 N2 C8 108.8(3) . . ?
C11 N2 H13 125.6 . . ?
C8 N2 H13 125.6 . . ?
C19 N3 C27 110.9(2) . . ?
C19 N3 C31 111.1(2) . . ?
C27 N3 C31 106.1(2) . . ?
C19 N3 C23 106.6(2) . . ?
C27 N3 C23 111.3(2) . . ?
C31 N3 C23 110.9(2) . . ?
C5 O1 B1 120.3(2) . . ?
C7 O2 B1 119.1(2) . . ?
F1 B1 O2 106.2(2) . . ?
F1 B1 O1 107.6(3) . . ?
O2 B1 O1 109.9(2) . . ?
F1 B1 C14 112.9(3) . . ?
O2 B1 C14 110.4(3) . . ?
O1 B1 C14 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
N1 C1 C2 C3 -1.1(4) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C3 C4 N1 0.0(4) . . . . ?
C2 C3 C4 C5 177.4(3) . . . . ?
N1 C4 C5 O1 178.1(3) . . . . ?
C3 C4 C5 O1 1.1(5) . . . . ?
N1 C4 C5 C6 0.8(5) . . . . ?
C3 C4 C5 C6 -176.2(3) . . . . ?
O1 C5 C6 C7 -8.4(5) . . . . ?
C4 C5 C6 C7 168.7(3) . . . . ?
C5 C6 C7 O2 2.9(4) . . . . ?
C5 C6 C7 C8 -173.3(3) . . . . ?
O2 C7 C8 N2 -175.6(3) . . . . ?
C6 C7 C8 N2 0.9(5) . . . . ?
O2 C7 C8 C9 5.9(5) . . . . ?
C6 C7 C8 C9 -177.6(3) . . . . ?
N2 C8 C9 C10 -1.1(3) . . . . ?
C7 C8 C9 C10 177.6(3) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C9 C10 C11 N2 -0.4(4) . . . . ?
C17 C12 C13 C14 1.8(5) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
C12 C13 C14 B1 -179.5(3) . . . . ?
C13 C14 C15 C16 -0.5(4) . . . . ?
B1 C14 C15 C16 178.2(3) . . . . ?
C14 C15 C16 C17 0.8(5) . . . . ?
C15 C16 C17 C12 0.1(5) . . . . ?
C15 C16 C17 C18 179.0(3) . . . . ?
C13 C12 C17 C16 -1.4(5) . . . . ?
C13 C12 C17 C18 179.7(3) . . . . ?
C16 C17 C18 O3 -168.1(3) . . . . ?
C12 C17 C18 O3 10.8(5) . . . . ?
C16 C17 C18 O4 10.7(5) . . . . ?
C12 C17 C18 O4 -170.5(3) . . . . ?
N3 C19 C20 C21 -175.0(3) . . . . ?
C19 C20 C21 C22 68.5(5) . . . . ?
N3 C23 C24 C25 178.8(3) . . . . ?
C23 C24 C25 C26 175.2(3) . . . . ?
N3 C27 C28 C29 164.4(3) . . . . ?
C27 C28 C29 C30 174.9(3) . . . . ?
N3 C31 C32 C33 -177.4(3) . . . . ?
C31 C32 C33 C35 -75.8(10) . . . . ?
C31 C32 C33 C34 -172.7(4) . . . . ?
C2 C1 N1 C4 1.1(3) . . . . ?
C3 C4 N1 C1 -0.7(3) . . . . ?
C5 C4 N1 C1 -178.3(3) . . . . ?
C10 C11 N2 C8 -0.3(4) . . . . ?
C9 C8 N2 C11 0.9(3) . . . . ?
C7 C8 N2 C11 -178.0(3) . . . . ?
C20 C19 N3 C27 -54.9(4) . . . . ?
C20 C19 N3 C31 62.8(4) . . . . ?
C20 C19 N3 C23 -176.2(3) . . . . ?
C28 C27 N3 C19 -63.8(3) . . . . ?
C28 C27 N3 C31 175.4(3) . . . . ?
C28 C27 N3 C23 54.6(3) . . . . ?
C32 C31 N3 C19 61.4(4) . . . . ?
C32 C31 N3 C27 -177.9(3) . . . . ?
C32 C31 N3 C23 -56.9(4) . . . . ?
C24 C23 N3 C19 179.2(3) . . . . ?
C24 C23 N3 C27 58.1(3) . . . . ?
C24 C23 N3 C31 -59.7(3) . . . . ?
C6 C5 O1 B1 -9.2(4) . . . . ?
C4 C5 O1 B1 173.4(3) . . . . ?
C6 C7 O2 B1 19.7(4) . . . . ?
C8 C7 O2 B1 -163.7(2) . . . . ?
C7 O2 B1 F1 82.5(3) . . . . ?
C7 O2 B1 O1 -33.6(4) . . . . ?
C7 O2 B1 C14 -154.7(2) . . . . ?
C5 O1 B1 F1 -86.7(3) . . . . ?
C5 O1 B1 O2 28.5(4) . . . . ?
C5 O1 B1 C14 150.1(3) . . . . ?
C13 C14 B1 F1 -118.8(3) . . . . ?
C15 C14 B1 F1 62.5(4) . . . . ?
C13 C14 B1 O2 122.4(3) . . . . ?
C15 C14 B1 O2 -56.2(4) . . . . ?
C13 C14 B1 O1 1.2(4) . . . . ?
C15 C14 B1 O1 -177.5(3) . . . . ?

_refine_diff_density_max         0.579
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.140



####################################################################### 
# 
# 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_resol2
_database_code_depnum_ccdc_archive 'CCDC 2086728'
loop_
_audit_author_name
_audit_author_address
'Nobuhiro Yasuda'
;Japan Synchrotron Radiation Research Institute
Japan
;
_audit_update_record             
;
2021-05-29 deposited with the CCDC.	2021-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H22 B F N2 O2, C12 H28 N, Cl'
_chemical_formula_sum            'C41 H50 B Cl F N3 O2'
_chemical_formula_weight         682.10

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'
F F 0.0727 0.0534 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   ' P 21 21 21 '
_symmetry_space_group_name_Hall  ' P 2ac 2ab '
_symmetry_Int_Tables_number      19

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

_cell_length_a                   8.819(4)
_cell_length_b                   19.343(7)
_cell_length_c                   22.015(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3755(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    3162
_cell_measurement_theta_min      25.84
_cell_measurement_theta_max      68.25

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456
_exptl_absorpt_coefficient_mu    1.238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8656
_exptl_absorpt_correction_T_max  0.9521
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            49016
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         6.79
_diffrn_reflns_theta_max         68.24
_reflns_number_total             6867
_reflns_number_gt                5818
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0735P)²+0.8239P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.995(16)
_refine_ls_number_reflns         6867
_refine_ls_number_parameters     446
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1281
_refine_ls_wR_factor_gt          0.1221
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.85496(9) 0.05646(3) 0.07278(3) 0.05364(18) Uani 1 1 d . . .
O1 O 0.6082(2) -0.03641(9) 0.28885(8) 0.0459(4) Uani 1 1 d . . .
F1 F 0.5316(2) 0.01447(9) 0.37898(7) 0.0632(5) Uani 1 1 d . . .
N3 N 0.3431(2) 0.02467(11) 0.01649(9) 0.0437(5) Uani 1 1 d . . .
O2 O 0.6166(2) 0.08790(9) 0.30364(7) 0.0466(4) Uani 1 1 d . . .
N1 N 0.8200(2) 0.17346(10) 0.18305(9) 0.0408(5) Uani 1 1 d . . .
H1 H 0.8305 0.1449 0.1522 0.049 Uiso 1 1 calc R . .
C1 C 0.6756(3) 0.03824(12) 0.20939(11) 0.0404(5) Uani 1 1 d . . .
H2 H 0.6888 0.0449 0.1670 0.049 Uiso 1 1 calc R . .
N2 N 0.7834(2) -0.08851(10) 0.14788(10) 0.0427(5) Uani 1 1 d . . .
H3 H 0.8062 -0.0513 0.1268 0.051 Uiso 1 1 calc R . .
C2 C 0.7064(3) -0.08879(13) 0.20241(12) 0.0430(6) Uani 1 1 d . . .
C3 C 0.8187(3) -0.15439(13) 0.13151(12) 0.0483(6) Uani 1 1 d . . .
C4 C 0.7378(3) 0.15995(13) 0.23522(11) 0.0436(6) Uani 1 1 d . . .
C5 C 0.9804(3) 0.26705(13) 0.13970(12) 0.0447(6) Uani 1 1 d . . .
C6 C 0.8819(3) 0.23749(12) 0.18662(12) 0.0462(6) Uani 1 1 d . . .
C7 C 0.9899(4) 0.24033(13) 0.08135(13) 0.0521(7) Uani 1 1 d . . .
H4 H 0.9311 0.2011 0.0705 0.063 Uiso 1 1 calc R . .
C8 C 1.0701(3) 0.32444(14) 0.15388(13) 0.0535(7) Uani 1 1 d . . .
H5 H 1.0651 0.3438 0.1935 0.064 Uiso 1 1 calc R . .
C30 C 0.4403(4) -0.05504(18) -0.06928(15) 0.0674(8) Uani 1 1 d . . .
H6 H 0.3567 -0.0417 -0.0969 0.081 Uiso 1 1 calc R . .
H7 H 0.4093 -0.0972 -0.0470 0.081 Uiso 1 1 calc R . .
C9 C 0.1372(4) -0.02003(18) 0.24267(18) 0.0731(9) Uani 1 1 d . . .
H8 H 0.0850 -0.0600 0.2287 0.088 Uiso 1 1 calc R . .
C10 C 0.6596(3) -0.02733(13) 0.23318(10) 0.0395(5) Uani 1 1 d . . .
C31 C 0.3328(6) -0.1362(2) 0.12074(18) 0.0864(12) Uani 1 1 d . . .
H9 H 0.2390 -0.1250 0.1425 0.130 Uiso 1 1 calc R . .
H10 H 0.4058 -0.1567 0.1491 0.130 Uiso 1 1 calc R . .
H11 H 0.3106 -0.1692 0.0881 0.130 Uiso 1 1 calc R . .
C11 C 0.9031(4) -0.12823(15) 0.02592(14) 0.0576(7) Uani 1 1 d . . .
H12 H 0.8529 -0.0848 0.0279 0.069 Uiso 1 1 calc R . .
C32 C 0.2416(4) 0.11357(18) -0.05966(17) 0.0675(9) Uani 1 1 d . . .
H13 H 0.3171 0.1007 -0.0910 0.081 Uiso 1 1 calc R . .
H14 H 0.2857 0.1509 -0.0345 0.081 Uiso 1 1 calc R . .
C12 C 0.6920(4) -0.15719(14) 0.22026(13) 0.0544(7) Uani 1 1 d . . .
H15 H 0.6428 -0.1734 0.2559 0.065 Uiso 1 1 calc R . .
C13 C 0.7624(4) -0.19763(14) 0.17648(14) 0.0586(8) Uani 1 1 d . . .
H16 H 0.7706 -0.2466 0.1772 0.070 Uiso 1 1 calc R . .
C14 C 0.6719(3) 0.09426(12) 0.24887(11) 0.0406(5) Uani 1 1 d . . .
C15 C 0.8997(3) -0.17204(13) 0.07575(14) 0.0523(7) Uani 1 1 d . . .
C16 C 0.7491(4) 0.21763(15) 0.27175(14) 0.0589(8) Uani 1 1 d . . .
H17 H 0.7042 0.2233 0.3107 0.071 Uiso 1 1 calc R . .
C33 C 0.2088(3) 0.05179(15) -0.02022(12) 0.0479(6) Uani 1 1 d . . .
H18 H 0.1709 0.0139 -0.0464 0.057 Uiso 1 1 calc R . .
H19 H 0.1264 0.0641 0.0083 0.057 Uiso 1 1 calc R . .
C17 C 1.0845(4) 0.27043(15) 0.03881(13) 0.0601(8) Uani 1 1 d . . .
H20 H 1.0890 0.2519 -0.0011 0.072 Uiso 1 1 calc R . .
C18 C 0.8373(4) 0.26565(14) 0.24178(14) 0.0620(8) Uani 1 1 d . . .
H21 H 0.8631 0.3103 0.2564 0.074 Uiso 1 1 calc R . .
C19 C 0.3593(3) 0.03046(14) 0.28919(11) 0.0472(6) Uani 1 1 d . . .
C34 C 0.4076(3) 0.08056(15) 0.05757(12) 0.0514(6) Uani 1 1 d . . .
H22 H 0.4978 0.0614 0.0784 0.062 Uiso 1 1 calc R . .
H23 H 0.4428 0.1192 0.0316 0.062 Uiso 1 1 calc R . .
C35 C 0.2845(3) -0.03584(15) 0.05341(12) 0.0513(6) Uani 1 1 d . . .
H24 H 0.1998 -0.0193 0.0791 0.062 Uiso 1 1 calc R . .
H25 H 0.2427 -0.0707 0.0251 0.062 Uiso 1 1 calc R . .
C36 C 0.4717(3) 0.00281(15) -0.02493(13) 0.0498(6) Uani 1 1 d . . .
H26 H 0.5043 0.0438 -0.0485 0.060 Uiso 1 1 calc R . .
H27 H 0.5583 -0.0113 0.0009 0.060 Uiso 1 1 calc R . .
C37 C 0.0995(4) 0.13972(17) -0.09028(16) 0.0683(9) Uani 1 1 d . . .
H28 H 0.0573 0.1033 -0.1162 0.102 Uiso 1 1 calc R . .
H29 H 0.1241 0.1802 -0.1152 0.102 Uiso 1 1 calc R . .
H30 H 0.0248 0.1527 -0.0594 0.102 Uiso 1 1 calc R . .
C20 C 0.2797(4) -0.02629(16) 0.26794(15) 0.0608(8) Uani 1 1 d . . .
H31 H 0.3245 -0.0708 0.2708 0.073 Uiso 1 1 calc R . .
C21 C 1.1724(4) 0.32696(15) 0.05363(15) 0.0596(8) Uani 1 1 d . . .
H32 H 1.2370 0.3474 0.0242 0.072 Uiso 1 1 calc R . .
C22 C 0.2875(4) 0.09409(16) 0.28455(16) 0.0638(8) Uani 1 1 d . . .
H33 H 0.3382 0.1341 0.2991 0.077 Uiso 1 1 calc R . .
B1 B 0.5266(4) 0.02369(16) 0.31675(13) 0.0453(7) Uani 1 1 d . . .
C23 C 1.1653(4) 0.35332(15) 0.11164(15) 0.0590(7) Uani 1 1 d . . .
H34 H 1.2266 0.3918 0.1225 0.071 Uiso 1 1 calc R . .
C24 C 1.0534(5) -0.2091(2) -0.02980(19) 0.0855(12) Uani 1 1 d . . .
H35 H 1.1053 -0.2219 -0.0659 0.103 Uiso 1 1 calc R . .
C38 C 0.3992(4) -0.07090(17) 0.09375(16) 0.0697(9) Uani 1 1 d . . .
H36 H 0.4297 -0.0391 0.1268 0.084 Uiso 1 1 calc R . .
H37 H 0.4908 -0.0825 0.0698 0.084 Uiso 1 1 calc R . .
C39 C 0.3756(5) 0.17314(18) 0.13361(17) 0.0763(10) Uani 1 1 d . . .
H38 H 0.4752 0.1608 0.1501 0.114 Uiso 1 1 calc R . .
H39 H 0.3107 0.1903 0.1664 0.114 Uiso 1 1 calc R . .
H40 H 0.3877 0.2092 0.1027 0.114 Uiso 1 1 calc R . .
C40 C 0.3030(4) 0.10964(17) 0.10497(15) 0.0667(8) Uani 1 1 d . . .
H41 H 0.2832 0.0744 0.1366 0.080 Uiso 1 1 calc R . .
H42 H 0.2050 0.1225 0.0861 0.080 Uiso 1 1 calc R . .
C25 C 1.0529(5) -0.2528(2) 0.0194(2) 0.0884(12) Uani 1 1 d . . .
H43 H 1.1053 -0.2956 0.0174 0.106 Uiso 1 1 calc R . .
C26 C 0.1453(4) 0.10100(19) 0.25953(19) 0.0760(10) Uani 1 1 d . . .
H44 H 0.0986 0.1452 0.2573 0.091 Uiso 1 1 calc R . .
C27 C 0.0711(4) 0.0435(2) 0.23775(19) 0.0788(10) Uani 1 1 d . . .
H45 H -0.0259 0.0481 0.2194 0.095 Uiso 1 1 calc R . .
C28 C 0.9786(5) -0.14685(18) -0.02666(16) 0.0732(9) Uani 1 1 d . . .
H46 H 0.9788 -0.1166 -0.0606 0.088 Uiso 1 1 calc R . .
C29 C 0.9768(4) -0.23474(16) 0.07164(17) 0.0721(9) Uani 1 1 d . . .
H47 H 0.9769 -0.2654 0.1053 0.087 Uiso 1 1 calc R . .
C41 C 0.5822(5) -0.0694(2) -0.10565(17) 0.0836(11) Uani 1 1 d . . .
H48 H 0.6136 -0.0273 -0.1269 0.125 Uiso 1 1 calc R . .
H49 H 0.5616 -0.1059 -0.1354 0.125 Uiso 1 1 calc R . .
H50 H 0.6634 -0.0844 -0.0783 0.125 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.318(3) . ?
O1 B1 1.499(4) . ?
F1 B1 1.382(3) . ?
N3 C35 1.516(3) . ?
N3 C36 1.515(3) . ?
N3 C34 1.520(3) . ?
N3 C33 1.527(3) . ?
O2 C14 1.306(3) . ?
O2 B1 1.502(4) . ?
N1 C6 1.356(3) . ?
N1 C4 1.383(3) . ?
N1 H1 0.8800 . ?
C1 C10 1.379(3) . ?
C1 C14 1.390(3) . ?
C1 H2 0.9500 . ?
N2 C3 1.361(3) . ?
N2 C2 1.379(3) . ?
N2 H3 0.8800 . ?
C2 C12 1.386(4) . ?
C2 C10 1.429(4) . ?
C3 C13 1.388(4) . ?
C3 C15 1.460(4) . ?
C4 C16 1.379(4) . ?
C4 C14 1.429(4) . ?
C5 C7 1.387(4) . ?
C5 C8 1.399(4) . ?
C5 C6 1.466(4) . ?
C6 C18 1.388(4) . ?
C7 C17 1.383(4) . ?
C7 H4 0.9500 . ?
C8 C23 1.371(4) . ?
C8 H5 0.9500 . ?
C30 C36 1.511(4) . ?
C30 C41 1.511(5) . ?
C30 H6 0.9900 . ?
C30 H7 0.9900 . ?
C9 C27 1.365(5) . ?
C9 C20 1.380(5) . ?
C9 H8 0.9500 . ?
C31 C38 1.514(5) . ?
C31 H9 0.9800 . ?
C31 H10 0.9800 . ?
C31 H11 0.9800 . ?
C11 C28 1.383(5) . ?
C11 C15 1.386(4) . ?
C11 H12 0.9500 . ?
C32 C33 1.505(4) . ?
C32 C37 1.510(5) . ?
C32 H13 0.9900 . ?
C32 H14 0.9900 . ?
C12 C13 1.388(4) . ?
C12 H15 0.9500 . ?
C13 H16 0.9500 . ?
C15 C29 1.393(4) . ?
C16 C18 1.379(4) . ?
C16 H17 0.9500 . ?
C33 H18 0.9900 . ?
C33 H19 0.9900 . ?
C17 C21 1.379(5) . ?
C17 H20 0.9500 . ?
C18 H21 0.9500 . ?
C19 C20 1.385(4) . ?
C19 C22 1.388(4) . ?
C19 B1 1.600(4) . ?
C34 C40 1.502(4) . ?
C34 H22 0.9900 . ?
C34 H23 0.9900 . ?
C35 C38 1.508(4) . ?
C35 H24 0.9900 . ?
C35 H25 0.9900 . ?
C36 H26 0.9900 . ?
C36 H27 0.9900 . ?
C37 H28 0.9800 . ?
C37 H29 0.9800 . ?
C37 H30 0.9800 . ?
C20 H31 0.9500 . ?
C21 C23 1.377(5) . ?
C21 H32 0.9500 . ?
C22 C26 1.376(5) . ?
C22 H33 0.9500 . ?
C23 H34 0.9500 . ?
C24 C28 1.375(5) . ?
C24 C25 1.374(6) . ?
C24 H35 0.9500 . ?
C38 H36 0.9900 . ?
C38 H37 0.9900 . ?
C39 C40 1.522(5) . ?
C39 H38 0.9800 . ?
C39 H39 0.9800 . ?
C39 H40 0.9800 . ?
C40 H41 0.9900 . ?
C40 H42 0.9900 . ?
C25 C29 1.376(5) . ?
C25 H43 0.9500 . ?
C26 C27 1.376(5) . ?
C26 H44 0.9500 . ?
C27 H45 0.9500 . ?
C28 H46 0.9500 . ?
C29 H47 0.9500 . ?
C41 H48 0.9800 . ?
C41 H49 0.9800 . ?
C41 H50 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 B1 116.27(19) . . ?
C35 N3 C36 111.2(2) . . ?
C35 N3 C34 111.0(2) . . ?
C36 N3 C34 106.1(2) . . ?
C35 N3 C33 106.54(19) . . ?
C36 N3 C33 110.97(19) . . ?
C34 N3 C33 111.2(2) . . ?
C14 O2 B1 116.90(19) . . ?
C6 N1 C4 109.6(2) . . ?
C6 N1 H1 125.2 . . ?
C4 N1 H1 125.2 . . ?
C10 C1 C14 118.5(2) . . ?
C10 C1 H2 120.7 . . ?
C14 C1 H2 120.7 . . ?
C3 N2 C2 109.9(2) . . ?
C3 N2 H3 125.1 . . ?
C2 N2 H3 125.1 . . ?
N2 C2 C12 107.2(2) . . ?
N2 C2 C10 123.5(2) . . ?
C12 C2 C10 129.3(2) . . ?
N2 C3 C13 107.1(2) . . ?
N2 C3 C15 123.6(2) . . ?
C13 C3 C15 129.3(2) . . ?
C16 C4 N1 107.1(2) . . ?
C16 C4 C14 128.8(2) . . ?
N1 C4 C14 123.8(2) . . ?
C7 C5 C8 117.9(3) . . ?
C7 C5 C6 122.9(2) . . ?
C8 C5 C6 119.2(2) . . ?
N1 C6 C18 107.2(2) . . ?
N1 C6 C5 123.7(2) . . ?
C18 C6 C5 129.2(2) . . ?
C17 C7 C5 120.5(3) . . ?
C17 C7 H4 119.8 . . ?
C5 C7 H4 119.8 . . ?
C23 C8 C5 121.2(3) . . ?
C23 C8 H5 119.4 . . ?
C5 C8 H5 119.4 . . ?
C36 C30 C41 109.1(3) . . ?
C36 C30 H6 109.9 . . ?
C41 C30 H6 109.9 . . ?
C36 C30 H7 109.9 . . ?
C41 C30 H7 109.9 . . ?
H6 C30 H7 108.3 . . ?
C27 C9 C20 120.0(3) . . ?
C27 C9 H8 120.0 . . ?
C20 C9 H8 120.0 . . ?
O1 C10 C1 120.7(2) . . ?
O1 C10 C2 115.4(2) . . ?
C1 C10 C2 123.7(2) . . ?
C38 C31 H9 109.5 . . ?
C38 C31 H10 109.5 . . ?
H9 C31 H10 109.5 . . ?
C38 C31 H11 109.5 . . ?
H9 C31 H11 109.5 . . ?
H10 C31 H11 109.5 . . ?
C28 C11 C15 120.9(3) . . ?
C28 C11 H12 119.6 . . ?
C15 C11 H12 119.6 . . ?
C33 C32 C37 111.4(3) . . ?
C33 C32 H13 109.4 . . ?
C37 C32 H13 109.4 . . ?
C33 C32 H14 109.4 . . ?
C37 C32 H14 109.4 . . ?
H13 C32 H14 108.0 . . ?
C2 C12 C13 107.5(3) . . ?
C2 C12 H15 126.3 . . ?
C13 C12 H15 126.3 . . ?
C12 C13 C3 108.4(2) . . ?
C12 C13 H16 125.8 . . ?
C3 C13 H16 125.8 . . ?
O2 C14 C1 120.8(2) . . ?
O2 C14 C4 115.4(2) . . ?
C1 C14 C4 123.5(2) . . ?
C11 C15 C29 118.0(3) . . ?
C11 C15 C3 122.2(2) . . ?
C29 C15 C3 119.8(3) . . ?
C4 C16 C18 107.9(3) . . ?
C4 C16 H17 126.1 . . ?
C18 C16 H17 126.1 . . ?
C32 C33 N3 115.4(2) . . ?
C32 C33 H18 108.4 . . ?
N3 C33 H18 108.4 . . ?
C32 C33 H19 108.4 . . ?
N3 C33 H19 108.4 . . ?
H18 C33 H19 107.5 . . ?
C21 C17 C7 120.8(3) . . ?
C21 C17 H20 119.6 . . ?
C7 C17 H20 119.6 . . ?
C16 C18 C6 108.3(2) . . ?
C16 C18 H21 125.9 . . ?
C6 C18 H21 125.9 . . ?
C20 C19 C22 116.5(3) . . ?
C20 C19 B1 122.1(2) . . ?
C22 C19 B1 121.4(3) . . ?
C40 C34 N3 116.7(2) . . ?
C40 C34 H22 108.1 . . ?
N3 C34 H22 108.1 . . ?
C40 C34 H23 108.1 . . ?
N3 C34 H23 108.1 . . ?
H22 C34 H23 107.3 . . ?
C38 C35 N3 115.7(2) . . ?
C38 C35 H24 108.3 . . ?
N3 C35 H24 108.3 . . ?
C38 C35 H25 108.3 . . ?
N3 C35 H25 108.3 . . ?
H24 C35 H25 107.4 . . ?
C30 C36 N3 117.3(2) . . ?
C30 C36 H26 108.0 . . ?
N3 C36 H26 108.0 . . ?
C30 C36 H27 108.0 . . ?
N3 C36 H27 108.0 . . ?
H26 C36 H27 107.2 . . ?
C32 C37 H28 109.5 . . ?
C32 C37 H29 109.5 . . ?
H28 C37 H29 109.5 . . ?
C32 C37 H30 109.5 . . ?
H28 C37 H30 109.5 . . ?
H29 C37 H30 109.5 . . ?
C9 C20 C19 121.9(3) . . ?
C9 C20 H31 119.0 . . ?
C19 C20 H31 119.0 . . ?
C23 C21 C17 119.2(3) . . ?
C23 C21 H32 120.4 . . ?
C17 C21 H32 120.4 . . ?
C26 C22 C19 122.1(3) . . ?
C26 C22 H33 119.0 . . ?
C19 C22 H33 119.0 . . ?
F1 B1 O1 106.9(2) . . ?
F1 B1 O2 106.3(2) . . ?
O1 B1 O2 108.0(2) . . ?
F1 B1 C19 114.6(2) . . ?
O1 B1 C19 110.5(2) . . ?
O2 B1 C19 110.3(2) . . ?
C8 C23 C21 120.4(3) . . ?
C8 C23 H34 119.8 . . ?
C21 C23 H34 119.8 . . ?
C28 C24 C25 119.8(3) . . ?
C28 C24 H35 120.1 . . ?
C25 C24 H35 120.1 . . ?
C35 C38 C31 110.3(3) . . ?
C35 C38 H36 109.6 . . ?
C31 C38 H36 109.6 . . ?
C35 C38 H37 109.6 . . ?
C31 C38 H37 109.6 . . ?
H36 C38 H37 108.1 . . ?
C40 C39 H38 109.5 . . ?
C40 C39 H39 109.5 . . ?
H38 C39 H39 109.5 . . ?
C40 C39 H40 109.5 . . ?
H38 C39 H40 109.5 . . ?
H39 C39 H40 109.5 . . ?
C34 C40 C39 109.4(3) . . ?
C34 C40 H41 109.8 . . ?
C39 C40 H41 109.8 . . ?
C34 C40 H42 109.8 . . ?
C39 C40 H42 109.8 . . ?
H41 C40 H42 108.2 . . ?
C29 C25 C24 120.3(3) . . ?
C29 C25 H43 119.8 . . ?
C24 C25 H43 119.8 . . ?
C27 C26 C22 119.6(3) . . ?
C27 C26 H44 120.2 . . ?
C22 C26 H44 120.2 . . ?
C9 C27 C26 119.8(3) . . ?
C9 C27 H45 120.1 . . ?
C26 C27 H45 120.1 . . ?
C24 C28 C11 120.1(3) . . ?
C24 C28 H46 120.0 . . ?
C11 C28 H46 120.0 . . ?
C25 C29 C15 120.9(3) . . ?
C25 C29 H47 119.6 . . ?
C15 C29 H47 119.6 . . ?
C30 C41 H48 109.5 . . ?
C30 C41 H49 109.5 . . ?
H48 C41 H49 109.5 . . ?
C30 C41 H50 109.5 . . ?
H48 C41 H50 109.5 . . ?
H49 C41 H50 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 C2 C12 -0.7(3) . . . . ?
C3 N2 C2 C10 177.0(2) . . . . ?
C2 N2 C3 C13 0.3(3) . . . . ?
C2 N2 C3 C15 179.6(2) . . . . ?
C6 N1 C4 C16 0.3(3) . . . . ?
C6 N1 C4 C14 -173.0(2) . . . . ?
C4 N1 C6 C18 -0.6(3) . . . . ?
C4 N1 C6 C5 177.8(2) . . . . ?
C7 C5 C6 N1 16.4(4) . . . . ?
C8 C5 C6 N1 -163.2(3) . . . . ?
C7 C5 C6 C18 -165.7(3) . . . . ?
C8 C5 C6 C18 14.8(4) . . . . ?
C8 C5 C7 C17 -0.6(4) . . . . ?
C6 C5 C7 C17 179.8(3) . . . . ?
C7 C5 C8 C23 -0.3(4) . . . . ?
C6 C5 C8 C23 179.3(3) . . . . ?
B1 O1 C10 C1 17.7(3) . . . . ?
B1 O1 C10 C2 -166.7(2) . . . . ?
C14 C1 C10 O1 15.2(4) . . . . ?
C14 C1 C10 C2 -160.0(2) . . . . ?
N2 C2 C10 O1 -170.1(2) . . . . ?
C12 C2 C10 O1 7.1(4) . . . . ?
N2 C2 C10 C1 5.4(4) . . . . ?
C12 C2 C10 C1 -177.5(3) . . . . ?
N2 C2 C12 C13 0.7(3) . . . . ?
C10 C2 C12 C13 -176.8(3) . . . . ?
C2 C12 C13 C3 -0.6(4) . . . . ?
N2 C3 C13 C12 0.2(3) . . . . ?
C15 C3 C13 C12 -179.1(3) . . . . ?
B1 O2 C14 C1 -13.6(3) . . . . ?
B1 O2 C14 C4 171.3(2) . . . . ?
C10 C1 C14 O2 -17.5(4) . . . . ?
C10 C1 C14 C4 157.2(2) . . . . ?
C16 C4 C14 O2 -0.9(4) . . . . ?
N1 C4 C14 O2 170.8(2) . . . . ?
C16 C4 C14 C1 -175.8(3) . . . . ?
N1 C4 C14 C1 -4.1(4) . . . . ?
C28 C11 C15 C29 1.1(5) . . . . ?
C28 C11 C15 C3 -178.9(3) . . . . ?
N2 C3 C15 C11 -22.1(4) . . . . ?
C13 C3 C15 C11 157.0(3) . . . . ?
N2 C3 C15 C29 157.8(3) . . . . ?
C13 C3 C15 C29 -23.0(5) . . . . ?
N1 C4 C16 C18 0.1(4) . . . . ?
C14 C4 C16 C18 172.9(3) . . . . ?
C37 C32 C33 N3 -175.7(3) . . . . ?
C35 N3 C33 C32 178.9(3) . . . . ?
C36 N3 C33 C32 -59.9(3) . . . . ?
C34 N3 C33 C32 57.8(3) . . . . ?
C5 C7 C17 C21 0.8(5) . . . . ?
C4 C16 C18 C6 -0.5(4) . . . . ?
N1 C6 C18 C16 0.6(4) . . . . ?
C5 C6 C18 C16 -177.6(3) . . . . ?
C35 N3 C34 C40 -57.0(3) . . . . ?
C36 N3 C34 C40 -178.0(3) . . . . ?
C33 N3 C34 C40 61.3(3) . . . . ?
C36 N3 C35 C38 59.1(3) . . . . ?
C34 N3 C35 C38 -58.7(3) . . . . ?
C33 N3 C35 C38 -179.8(3) . . . . ?
C41 C30 C36 N3 -179.4(3) . . . . ?
C35 N3 C36 C30 56.8(3) . . . . ?
C34 N3 C36 C30 177.5(2) . . . . ?
C33 N3 C36 C30 -61.7(3) . . . . ?
C27 C9 C20 C19 0.4(6) . . . . ?
C22 C19 C20 C9 0.9(5) . . . . ?
B1 C19 C20 C9 -178.2(3) . . . . ?
C7 C17 C21 C23 0.1(5) . . . . ?
C20 C19 C22 C26 -0.7(5) . . . . ?
B1 C19 C22 C26 178.3(3) . . . . ?
C10 O1 B1 F1 -158.6(2) . . . . ?
C10 O1 B1 O2 -44.6(3) . . . . ?
C10 O1 B1 C19 76.1(3) . . . . ?
C14 O2 B1 F1 157.0(2) . . . . ?
C14 O2 B1 O1 42.6(3) . . . . ?
C14 O2 B1 C19 -78.3(3) . . . . ?
C20 C19 B1 F1 -92.1(3) . . . . ?
C22 C19 B1 F1 88.9(3) . . . . ?
C20 C19 B1 O1 28.7(3) . . . . ?
C22 C19 B1 O1 -150.2(3) . . . . ?
C20 C19 B1 O2 148.1(3) . . . . ?
C22 C19 B1 O2 -30.9(3) . . . . ?
C5 C8 C23 C21 1.2(5) . . . . ?
C17 C21 C23 C8 -1.1(5) . . . . ?
N3 C35 C38 C31 -171.7(3) . . . . ?
N3 C34 C40 C39 -169.6(3) . . . . ?
C28 C24 C25 C29 0.5(7) . . . . ?
C19 C22 C26 C27 -0.6(6) . . . . ?
C20 C9 C27 C26 -1.7(6) . . . . ?
C22 C26 C27 C9 1.8(6) . . . . ?
C25 C24 C28 C11 0.0(6) . . . . ?
C15 C11 C28 C24 -0.9(5) . . . . ?
C24 C25 C29 C15 -0.3(6) . . . . ?
C11 C15 C29 C25 -0.6(5) . . . . ?
C3 C15 C29 C25 179.5(3) . . . . ?

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
N1 H1 Cl1 0.88 2.46 3.333(2) 174.8 .
N2 H3 Cl1 0.88 2.44 3.316(2) 175.7 .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        68.24
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.025
####################################################################### 
# 
# 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_50319ri
_database_code_depnum_ccdc_archive 'CCDC 2086727'
loop_
_audit_author_name
_audit_author_address
'Nobuhiro Yasuda'
;Japan Synchrotron Radiation Research Institute
Japan
;
_audit_update_record             
;
2021-05-29 deposited with the CCDC.	2021-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C28 H30 N3, C17 H14 B F N2 O2, 0.833(C H2 Cl2), 1.334(Cl), 0.17(C H2)'
_chemical_formula_sum            'C46 H46 B Cl3 F N5 O2'
_chemical_formula_weight         837.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Cl Cl 0.3639 0.7018 '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'
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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0150(8)
_cell_length_b                   11.0473(13)
_cell_length_c                   18.5628(16)
_cell_angle_alpha                88.109(9)
_cell_angle_beta                 76.917(5)
_cell_angle_gamma                87.736(10)
_cell_volume                     1998.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    2047
_cell_measurement_theta_min      25.3
_cell_measurement_theta_max      68.1

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             876
_exptl_absorpt_coefficient_mu    2.492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5421
_exptl_absorpt_correction_T_max  0.9069
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25109
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         6.86
_diffrn_reflns_theta_max         65.99
_reflns_number_total             6754
_reflns_number_gt                5723
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0679P)²+0.2646P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6754
_refine_ls_number_parameters     586
_refine_ls_number_restraints     174
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1091
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.003
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.28182(9) 1.55231(9) 0.43909(5) 0.0253(2) Uani 1 1 d . . .
O1 O 0.13936(11) 1.66376(10) 0.37698(6) 0.0226(3) Uani 1 1 d . . .
O2 O 0.34639(11) 1.55111(11) 0.31037(6) 0.0232(3) Uani 1 1 d . . .
C4 C 0.55497(15) 0.81595(15) 0.28789(9) 0.0187(3) Uani 1 1 d U . .
C5 C 0.58674(15) 0.69401(15) 0.39562(8) 0.0187(3) Uani 1 1 d . . .
C6 C 0.62702(15) 0.72407(15) 0.31876(9) 0.0194(3) Uani 1 1 d U B .
N1 N 0.47514(13) 0.75577(12) 0.43834(7) 0.0190(3) Uani 1 1 d . . .
N2 N 0.40658(13) 0.99320(13) 0.22547(7) 0.0219(3) Uani 1 1 d . . .
C9 C 0.44388(15) 0.87867(15) 0.33293(8) 0.0185(3) Uani 1 1 d . . .
C10 C 0.52117(16) 0.93831(15) 0.18049(9) 0.0222(4) Uani 1 1 d . . .
C11 C 0.66197(16) 0.60515(15) 0.42556(9) 0.0223(4) Uani 1 1 d . B .
H1 H 0.6393 0.5862 0.4771 0.027 Uiso 1 1 calc R . .
C12 C 0.59642(16) 0.84750(15) 0.21208(9) 0.0209(3) Uani 1 1 d U B .
C13 C 0.13671(15) 1.43244(15) 0.37612(8) 0.0193(3) Uani 1 1 d . . .
C14 C 0.32213(17) 1.07791(16) 0.18997(9) 0.0247(4) Uani 1 1 d . . .
H2 H 0.2268 1.0793 0.2199 0.030 Uiso 1 1 calc R . .
H3 H 0.3206 1.0476 0.1406 0.030 Uiso 1 1 calc R . .
C15 C 0.74304(16) 0.66484(16) 0.27385(9) 0.0234(4) Uani 1 1 d U . .
C16 C 0.11301(15) 1.38795(15) 0.31050(9) 0.0209(3) Uani 1 1 d . . .
H4 H 0.1564 1.4245 0.2646 0.025 Uiso 1 1 calc R . .
C17 C 0.37052(15) 0.97123(15) 0.30113(9) 0.0205(4) Uani 1 1 d . . .
C18 C 0.42784(16) 0.71859(16) 0.51672(8) 0.0219(4) Uani 1 1 d . . .
H5 H 0.4473 0.6306 0.5222 0.026 Uiso 1 1 calc R . .
H6 H 0.3273 0.7327 0.5318 0.026 Uiso 1 1 calc R . .
C19 C -0.08096(17) 1.84120(16) 0.37591(10) 0.0258(4) Uani 1 1 d . . .
H7 H -0.0994 1.8057 0.4243 0.031 Uiso 1 1 calc R . .
C20 C 0.75639(18) 0.82386(17) 0.09349(9) 0.0294(4) Uani 1 1 d U B .
H8 H 0.8352 0.7862 0.0631 0.035 Uiso 1 1 calc R . .
N4 N 0.01684(15) 1.88682(13) 0.25815(8) 0.0283(3) Uani 1 1 d . . .
H9 H 0.0743 1.8871 0.2146 0.034 Uiso 1 1 calc R . .
C23 C 0.53967(17) 1.49261(17) 0.17403(10) 0.0286(4) Uani 1 1 d . . .
H10 H 0.5620 1.4390 0.2109 0.034 Uiso 1 1 calc R . .
C24 C 0.81159(17) 0.57159(16) 0.30474(9) 0.0252(4) Uani 1 1 d U B .
H11 H 0.8857 0.5272 0.2748 0.030 Uiso 1 1 calc R . .
C25 C 0.29825(16) 0.91628(15) 0.45413(9) 0.0229(4) Uani 1 1 d . . .
H12 H 0.2719 0.8995 0.5058 0.027 Uiso 1 1 calc R . .
C26 C 0.77014(16) 0.54477(16) 0.37943(9) 0.0237(4) Uani 1 1 d U . .
H13 H 0.8182 0.4818 0.4001 0.028 Uiso 1 1 calc R B .
C27 C 0.40502(15) 0.84932(15) 0.40994(9) 0.0191(3) Uani 1 1 d . . .
C28 C 0.26421(16) 1.03645(16) 0.34734(9) 0.0240(4) Uani 1 1 d . . .
H14 H 0.2153 1.1000 0.3276 0.029 Uiso 1 1 calc R . .
C29 C 0.07161(15) 1.37411(15) 0.44225(9) 0.0212(3) Uani 1 1 d . . .
H15 H 0.0863 1.4013 0.4878 0.025 Uiso 1 1 calc R . .
C30 C 0.23130(16) 1.00721(16) 0.42198(9) 0.0242(4) Uani 1 1 d . . .
H16 H 0.1588 1.0520 0.4528 0.029 Uiso 1 1 calc R . .
C31 C -0.01349(16) 1.27792(15) 0.44312(9) 0.0225(4) Uani 1 1 d . . .
H17 H -0.0566 1.2404 0.4888 0.027 Uiso 1 1 calc R . .
C32 C 0.02767(16) 1.29169(16) 0.31078(9) 0.0234(4) Uani 1 1 d . . .
H18 H 0.0126 1.2637 0.2655 0.028 Uiso 1 1 calc R . .
C33 C 0.43800(17) 1.58329(16) 0.18472(9) 0.0252(4) Uani 1 1 d . . .
C34 C 0.68192(18) 0.91258(17) 0.06443(9) 0.0292(4) Uani 1 1 d U . .
H20 H 0.7116 0.9353 0.0137 0.035 Uiso 1 1 calc R . .
C35 C 0.71497(17) 0.78987(16) 0.16803(9) 0.0254(4) Uani 1 1 d U . .
C36 C 0.33543(16) 1.61229(15) 0.25038(9) 0.0217(4) Uani 1 1 d . . .
N5 N 0.44087(15) 1.63998(14) 0.11726(8) 0.0290(3) Uani 1 1 d . . .
H21 H 0.3863 1.7008 0.1091 0.035 Uiso 1 1 calc R . .
C38 C -0.03548(16) 1.23669(15) 0.37734(9) 0.0231(4) Uani 1 1 d . . .
H22 H -0.0938 1.1708 0.3778 0.028 Uiso 1 1 calc R . .
C39 C 0.56585(18) 0.97005(17) 0.10580(9) 0.0277(4) Uani 1 1 d . . .
H23 H 0.5171 1.0305 0.0836 0.033 Uiso 1 1 calc R . .
C40 C 0.37323(17) 1.20636(16) 0.18108(9) 0.0255(4) Uani 1 1 d . . .
H24 H 0.4734 1.2046 0.1601 0.031 Uiso 1 1 calc R . .
H25 H 0.3557 1.2442 0.2301 0.031 Uiso 1 1 calc R . .
C41 C 0.02979(17) 1.81380(15) 0.31836(9) 0.0234(4) Uani 1 1 d . . .
C42 C 0.23096(17) 1.69687(16) 0.24986(9) 0.0236(4) Uani 1 1 d . . .
H26 H 0.2235 1.7374 0.2049 0.028 Uiso 1 1 calc R . .
C43 C 0.13634(16) 1.72296(15) 0.31513(9) 0.0213(4) Uani 1 1 d . . .
C44 C 0.60335(19) 1.49478(19) 0.09863(10) 0.0354(5) Uani 1 1 d . . .
H27 H 0.6761 1.4423 0.0746 0.042 Uiso 1 1 calc R . .
C45 C -0.09784(19) 1.95727(17) 0.27694(11) 0.0336(4) Uani 1 1 d . . .
H28 H -0.1300 2.0154 0.2454 0.040 Uiso 1 1 calc R . .
C46 C 0.54072(19) 1.58716(19) 0.06597(10) 0.0347(4) Uani 1 1 d . . .
H29 H 0.5643 1.6102 0.0150 0.042 Uiso 1 1 calc R . .
C47 C -0.16037(19) 1.93124(17) 0.34901(11) 0.0341(4) Uani 1 1 d . . .
H30 H -0.2432 1.9679 0.3760 0.041 Uiso 1 1 calc R . .
C48 C 0.49561(18) 0.78627(17) 0.56810(9) 0.0270(4) Uani 1 1 d . . .
H31 H 0.4747 0.8742 0.5640 0.032 Uiso 1 1 calc R . .
H32 H 0.5963 0.7730 0.5533 0.032 Uiso 1 1 calc R . .
B1 B 0.22783(18) 1.54862(18) 0.37668(10) 0.0214(4) Uani 1 1 d . . .
C52 C 0.4438(2) 0.7421(2) 0.64787(10) 0.0407(5) Uani 1 1 d . . .
H38 H 0.3437 0.7526 0.6618 0.061 Uiso 1 1 calc R . .
H39 H 0.4848 0.7892 0.6807 0.061 Uiso 1 1 calc R . .
H40 H 0.4697 0.6562 0.6524 0.061 Uiso 1 1 calc R . .
Cl3 Cl 0.22985(5) 1.84996(4) 0.08273(2) 0.03689(14) Uani 1 1 d . . .
C54 C 0.30046(19) 1.28080(17) 0.13019(10) 0.0295(4) Uani 1 1 d . . .
H43 H 0.3210 1.2450 0.0811 0.044 Uiso 1 1 calc R . .
H44 H 0.3322 1.3641 0.1260 0.044 Uiso 1 1 calc R . .
H45 H 0.2013 1.2813 0.1507 0.044 Uiso 1 1 calc R . .
Cl1 Cl 0.77541(14) 0.22613(11) 0.17158(8) 0.0401(3) Uani 0.833(2) 1 d PU A 1
Cl2 Cl 1.00628(5) 0.08464(6) 0.08538(3) 0.0368(2) Uani 0.833(2) 1 d PU A 1
C1A C 0.8752(3) 0.1957(3) 0.08205(14) 0.0396(7) Uani 0.833(2) 1 d PU A 1
H46 H 0.8152 0.1670 0.0509 0.048 Uiso 0.833(2) 1 calc PR A 1
H47 H 0.9171 0.2713 0.0590 0.048 Uiso 0.833(2) 1 calc PR A 1
N3A N 0.7910(2) 0.7075(2) 0.20198(12) 0.0209(5) Uani 0.849(4) 1 d P B 1
C49 C 0.9304(2) 0.6691(2) 0.16201(12) 0.0241(6) Uani 0.849(4) 1 d P B 1
H33 H 0.9881 0.6546 0.1984 0.029 Uiso 0.849(4) 1 calc PR B 1
H34 H 0.9703 0.7364 0.1285 0.029 Uiso 0.849(4) 1 calc PR B 1
C53 C 0.9370(2) 0.5564(2) 0.11703(12) 0.0289(6) Uani 0.849(4) 1 d P B 1
H41 H 0.8842 0.5708 0.0783 0.035 Uiso 0.849(4) 1 calc PR B 1
H42 H 0.8959 0.4883 0.1495 0.035 Uiso 0.849(4) 1 calc PR B 1
C51A C 1.0855(5) 0.5243(4) 0.0814(3) 0.0321(9) Uani 0.849(4) 1 d P B 1
H35A H 1.1245 0.5904 0.0476 0.048 Uiso 0.849(4) 1 calc PR B 1
H36A H 1.0902 0.4497 0.0537 0.048 Uiso 0.849(4) 1 calc PR B 1
H37A H 1.1378 0.5121 0.1199 0.048 Uiso 0.849(4) 1 calc PR B 1
C1B C 0.8731(16) 0.1352(15) 0.0899(8) 0.0396(7) Uani 0.17 1 d P A 2
H48 H 0.9038 0.0501 0.0967 0.048 Uiso 0.167(2) 1 calc PR A 2
H49 H 0.8334 0.1407 0.0457 0.048 Uiso 0.167(2) 1 calc PR A 2
Cl4 Cl 1.0064(6) 0.2265(9) 0.0786(3) 0.170(5) Uani 0.167(2) 1 d P A 2
Cl5 Cl 0.7478(9) 0.1815(9) 0.1695(5) 0.073(2) Uani 0.167(2) 1 d P A 2
N3B N 0.7602(14) 0.6748(13) 0.1935(8) 0.0209(18) Uani 0.151(4) 1 d PU B 2
C51B C 1.108(3) 0.554(2) 0.0809(15) 0.022(4) Uani 0.151(4) 1 d PU B 2
H35B H 1.2007 0.5805 0.0793 0.034 Uiso 0.151(4) 1 calc PR B 2
H36B H 1.0895 0.5614 0.0312 0.034 Uiso 0.151(4) 1 calc PR B 2
H37B H 1.0994 0.4697 0.0985 0.034 Uiso 0.151(4) 1 calc PR B 2
C55 C 0.8558(12) 0.5992(10) 0.1447(6) 0.020(2) Uani 0.151(4) 1 d PU B 2
H50 H 0.8310 0.6013 0.0960 0.024 Uiso 0.151(4) 1 calc PR B 2
H51 H 0.8475 0.5147 0.1643 0.024 Uiso 0.151(4) 1 calc PR B 2
C56 C 1.0035(13) 0.6345(11) 0.1337(7) 0.023(3) Uani 0.151(4) 1 d PU B 2
H52 H 1.0281 0.6321 0.1825 0.028 Uiso 0.151(4) 1 calc PR B 2
H53 H 1.0113 0.7192 0.1145 0.028 Uiso 0.151(4) 1 calc PR B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.387(2) . ?
O1 C43 1.3082(19) . ?
O1 B1 1.521(2) . ?
O2 C36 1.3072(19) . ?
O2 B1 1.505(2) . ?
C4 C6 1.404(2) . ?
C4 C9 1.405(2) . ?
C4 C12 1.410(2) . ?
C5 N1 1.385(2) . ?
C5 C11 1.391(2) . ?
C5 C6 1.424(2) . ?
C6 C15 1.418(2) . ?
N1 C27 1.383(2) . ?
N1 C18 1.4745(19) . ?
N2 C17 1.384(2) . ?
N2 C10 1.388(2) . ?
N2 C14 1.474(2) . ?
C9 C17 1.425(2) . ?
C9 C27 1.424(2) . ?
C10 C39 1.394(2) . ?
C10 C12 1.421(2) . ?
C11 C26 1.383(2) . ?
C11 H1 0.9500 . ?
C12 C35 1.421(2) . ?
C13 C16 1.400(2) . ?
C13 C29 1.402(2) . ?
C13 B1 1.606(2) . ?
C14 C40 1.519(2) . ?
C14 H2 0.9900 . ?
C14 H3 0.9900 . ?
C15 N3A 1.385(3) . ?
C15 C24 1.395(2) . ?
C15 N3B 1.462(14) . ?
C16 C32 1.389(2) . ?
C16 H4 0.9500 . ?
C17 C28 1.398(2) . ?
C18 C48 1.520(2) . ?
C18 H5 0.9900 . ?
C18 H6 0.9900 . ?
C19 C41 1.386(2) . ?
C19 C47 1.399(3) . ?
C19 H7 0.9500 . ?
C20 C34 1.377(3) . ?
C20 C35 1.395(2) . ?
C20 H8 0.9500 . ?
N4 C45 1.346(2) . ?
N4 C41 1.384(2) . ?
N4 H9 0.8800 . ?
C23 C33 1.386(3) . ?
C23 C44 1.400(2) . ?
C23 H10 0.9500 . ?
C24 C26 1.380(2) . ?
C24 H11 0.9500 . ?
C25 C30 1.380(2) . ?
C25 C27 1.394(2) . ?
C25 H12 0.9500 . ?
C26 H13 0.9500 . ?
C28 C30 1.380(2) . ?
C28 H14 0.9500 . ?
C29 C31 1.386(2) . ?
C29 H15 0.9500 . ?
C30 H16 0.9500 . ?
C31 C38 1.383(2) . ?
C31 H17 0.9500 . ?
C32 C38 1.387(2) . ?
C32 H18 0.9500 . ?
C33 N5 1.376(2) . ?
C33 C36 1.441(2) . ?
C34 C39 1.383(3) . ?
C34 H20 0.9500 . ?
C35 N3A 1.389(3) . ?
C35 N3B 1.434(15) . ?
C36 C42 1.376(3) . ?
N5 C46 1.344(2) . ?
N5 H21 0.8800 . ?
C38 H22 0.9500 . ?
C39 H23 0.9500 . ?
C40 C54 1.521(2) . ?
C40 H24 0.9900 . ?
C40 H25 0.9900 . ?
C41 C43 1.428(3) . ?
C42 C43 1.390(2) . ?
C42 H26 0.9500 . ?
C44 C46 1.372(3) . ?
C44 H27 0.9500 . ?
C45 C47 1.369(3) . ?
C45 H28 0.9500 . ?
C46 H29 0.9500 . ?
C47 H30 0.9500 . ?
C48 C52 1.525(2) . ?
C48 H31 0.9900 . ?
C48 H32 0.9900 . ?
C52 H38 0.9800 . ?
C52 H39 0.9800 . ?
C52 H40 0.9800 . ?
C54 H43 0.9800 . ?
C54 H44 0.9800 . ?
C54 H45 0.9800 . ?
Cl1 C1A 1.770(3) . ?
Cl2 C1A 1.771(3) . ?
C1A H46 0.9900 . ?
C1A H47 0.9900 . ?
N3A C49 1.478(3) . ?
C49 C53 1.514(3) . ?
C49 H33 0.9900 . ?
C49 H34 0.9900 . ?
C53 C51A 1.518(5) . ?
C53 H41 0.9900 . ?
C53 H42 0.9900 . ?
C51A H35A 0.9800 . ?
C51A H36A 0.9800 . ?
C51A H37A 0.9800 . ?
C1B Cl4 1.675(16) . ?
C1B Cl5 1.783(18) . ?
C1B H48 0.9900 . ?
C1B H49 0.9900 . ?
N3B C55 1.425(19) . ?
C51B C56 1.54(3) . ?
C51B H35B 0.9800 . ?
C51B H36B 0.9800 . ?
C51B H37B 0.9800 . ?
C55 C56 1.512(16) . ?
C55 H50 0.9900 . ?
C55 H51 0.9900 . ?
C56 H52 0.9900 . ?
C56 H53 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C43 O1 B1 120.52(13) . . ?
C36 O2 B1 120.33(13) . . ?
C6 C4 C9 119.97(14) . . ?
C6 C4 C12 120.00(15) . . ?
C9 C4 C12 120.00(15) . . ?
N1 C5 C11 122.18(14) . . ?
N1 C5 C6 118.79(14) . . ?
C11 C5 C6 119.02(15) . . ?
C4 C6 C15 119.81(14) . . ?
C4 C6 C5 119.93(15) . . ?
C15 C6 C5 120.22(15) . . ?
C27 N1 C5 122.52(13) . . ?
C27 N1 C18 118.87(13) . . ?
C5 N1 C18 118.60(13) . . ?
C17 N2 C10 122.43(14) . . ?
C17 N2 C14 119.94(13) . . ?
C10 N2 C14 117.63(13) . . ?
C4 C9 C17 119.69(14) . . ?
C4 C9 C27 119.90(15) . . ?
C17 C9 C27 120.41(15) . . ?
N2 C10 C39 122.40(15) . . ?
N2 C10 C12 118.65(14) . . ?
C39 C10 C12 118.95(15) . . ?
C26 C11 C5 119.21(15) . . ?
C26 C11 H1 120.4 . . ?
C5 C11 H1 120.4 . . ?
C4 C12 C35 119.70(15) . . ?
C4 C12 C10 119.92(15) . . ?
C35 C12 C10 120.37(14) . . ?
C16 C13 C29 116.80(14) . . ?
C16 C13 B1 122.07(14) . . ?
C29 C13 B1 121.07(14) . . ?
N2 C14 C40 113.55(13) . . ?
N2 C14 H2 108.9 . . ?
C40 C14 H2 108.9 . . ?
N2 C14 H3 108.9 . . ?
C40 C14 H3 108.9 . . ?
H2 C14 H3 107.7 . . ?
N3A C15 C24 121.80(16) . . ?
N3A C15 C6 118.79(16) . . ?
C24 C15 C6 119.24(15) . . ?
N3A C15 N3B 21.4(5) . . ?
C24 C15 N3B 119.7(6) . . ?
C6 C15 N3B 118.1(6) . . ?
C32 C16 C13 121.74(15) . . ?
C32 C16 H4 119.1 . . ?
C13 C16 H4 119.1 . . ?
N2 C17 C28 122.22(15) . . ?
N2 C17 C9 118.88(14) . . ?
C28 C17 C9 118.90(14) . . ?
N1 C18 C48 113.08(12) . . ?
N1 C18 H5 109.0 . . ?
C48 C18 H5 109.0 . . ?
N1 C18 H6 109.0 . . ?
C48 C18 H6 109.0 . . ?
H5 C18 H6 107.8 . . ?
C41 C19 C47 106.78(16) . . ?
C41 C19 H7 126.6 . . ?
C47 C19 H7 126.6 . . ?
C34 C20 C35 119.34(16) . . ?
C34 C20 H8 120.3 . . ?
C35 C20 H8 120.3 . . ?
C45 N4 C41 109.03(15) . . ?
C45 N4 H9 125.5 . . ?
C41 N4 H9 125.5 . . ?
C33 C23 C44 107.20(16) . . ?
C33 C23 H10 126.4 . . ?
C44 C23 H10 126.4 . . ?
C26 C24 C15 119.00(16) . . ?
C26 C24 H11 120.5 . . ?
C15 C24 H11 120.5 . . ?
C30 C25 C27 119.30(15) . . ?
C30 C25 H12 120.4 . . ?
C27 C25 H12 120.4 . . ?
C24 C26 C11 123.12(16) . . ?
C24 C26 H13 118.4 . . ?
C11 C26 H13 118.4 . . ?
N1 C27 C25 122.33(14) . . ?
N1 C27 C9 118.79(14) . . ?
C25 C27 C9 118.88(15) . . ?
C30 C28 C17 119.04(16) . . ?
C30 C28 H14 120.5 . . ?
C17 C28 H14 120.5 . . ?
C31 C29 C13 121.91(15) . . ?
C31 C29 H15 119.0 . . ?
C13 C29 H15 119.0 . . ?
C25 C30 C28 123.41(16) . . ?
C25 C30 H16 118.3 . . ?
C28 C30 H16 118.3 . . ?
C38 C31 C29 119.84(15) . . ?
C38 C31 H17 120.1 . . ?
C29 C31 H17 120.1 . . ?
C38 C32 C16 119.78(15) . . ?
C38 C32 H18 120.1 . . ?
C16 C32 H18 120.1 . . ?
N5 C33 C23 107.64(15) . . ?
N5 C33 C36 122.62(16) . . ?
C23 C33 C36 129.51(16) . . ?
C20 C34 C39 122.98(16) . . ?
C20 C34 H20 118.5 . . ?
C39 C34 H20 118.5 . . ?
N3A C35 C20 122.16(17) . . ?
N3A C35 C12 118.64(16) . . ?
C20 C35 C12 119.05(16) . . ?
N3A C35 N3B 21.7(5) . . ?
C20 C35 N3B 119.7(6) . . ?
C12 C35 N3B 118.0(6) . . ?
O2 C36 C42 122.04(15) . . ?
O2 C36 C33 115.56(15) . . ?
C42 C36 C33 122.38(15) . . ?
C46 N5 C33 108.74(16) . . ?
C46 N5 H21 125.6 . . ?
C33 N5 H21 125.6 . . ?
C31 C38 C32 119.92(15) . . ?
C31 C38 H22 120.0 . . ?
C32 C38 H22 120.0 . . ?
C34 C39 C10 119.32(16) . . ?
C34 C39 H23 120.3 . . ?
C10 C39 H23 120.3 . . ?
C14 C40 C54 110.13(14) . . ?
C14 C40 H24 109.6 . . ?
C54 C40 H24 109.6 . . ?
C14 C40 H25 109.6 . . ?
C54 C40 H25 109.6 . . ?
H24 C40 H25 108.1 . . ?
N4 C41 C19 107.49(16) . . ?
N4 C41 C43 122.94(15) . . ?
C19 C41 C43 129.44(15) . . ?
C36 C42 C43 119.94(15) . . ?
C36 C42 H26 120.0 . . ?
C43 C42 H26 120.0 . . ?
O1 C43 C42 121.34(16) . . ?
O1 C43 C41 116.41(14) . . ?
C42 C43 C41 122.24(15) . . ?
C46 C44 C23 106.99(17) . . ?
C46 C44 H27 126.5 . . ?
C23 C44 H27 126.5 . . ?
N4 C45 C47 108.66(16) . . ?
N4 C45 H28 125.7 . . ?
C47 C45 H28 125.7 . . ?
N5 C46 C44 109.42(16) . . ?
N5 C46 H29 125.3 . . ?
C44 C46 H29 125.3 . . ?
C45 C47 C19 108.04(17) . . ?
C45 C47 H30 126.0 . . ?
C19 C47 H30 126.0 . . ?
C18 C48 C52 110.30(14) . . ?
C18 C48 H31 109.6 . . ?
C52 C48 H31 109.6 . . ?
C18 C48 H32 109.6 . . ?
C52 C48 H32 109.6 . . ?
H31 C48 H32 108.1 . . ?
F1 B1 O2 107.28(13) . . ?
F1 B1 O1 105.91(14) . . ?
O2 B1 O1 109.62(13) . . ?
F1 B1 C13 113.17(13) . . ?
O2 B1 C13 110.94(14) . . ?
O1 B1 C13 109.74(13) . . ?
C48 C52 H38 109.5 . . ?
C48 C52 H39 109.5 . . ?
H38 C52 H39 109.5 . . ?
C48 C52 H40 109.5 . . ?
H38 C52 H40 109.5 . . ?
H39 C52 H40 109.5 . . ?
C40 C54 H43 109.5 . . ?
C40 C54 H44 109.5 . . ?
H43 C54 H44 109.5 . . ?
C40 C54 H45 109.5 . . ?
H43 C54 H45 109.5 . . ?
H44 C54 H45 109.5 . . ?
Cl2 C1A Cl1 111.39(15) . . ?
Cl2 C1A H46 109.4 . . ?
Cl1 C1A H46 109.4 . . ?
Cl2 C1A H47 109.4 . . ?
Cl1 C1A H47 109.4 . . ?
H46 C1A H47 108.0 . . ?
C15 N3A C35 121.95(18) . . ?
C15 N3A C49 118.72(18) . . ?
C35 N3A C49 119.23(18) . . ?
N3A C49 C53 114.74(19) . . ?
N3A C49 H33 108.6 . . ?
C53 C49 H33 108.6 . . ?
N3A C49 H34 108.6 . . ?
C53 C49 H34 108.6 . . ?
H33 C49 H34 107.6 . . ?
C49 C53 C51A 109.4(2) . . ?
C49 C53 H41 109.8 . . ?
C51A C53 H41 109.8 . . ?
C49 C53 H42 109.8 . . ?
C51A C53 H42 109.8 . . ?
H41 C53 H42 108.2 . . ?
Cl4 C1B Cl5 108.4(9) . . ?
Cl4 C1B H48 110.0 . . ?
Cl5 C1B H48 110.0 . . ?
Cl4 C1B H49 110.0 . . ?
Cl5 C1B H49 110.0 . . ?
H48 C1B H49 108.4 . . ?
C55 N3B C35 120.5(11) . . ?
C55 N3B C15 121.9(11) . . ?
C35 N3B C15 113.8(9) . . ?
C56 C51B H35B 109.5 . . ?
C56 C51B H36B 109.5 . . ?
H35B C51B H36B 109.5 . . ?
C56 C51B H37B 109.5 . . ?
H35B C51B H37B 109.5 . . ?
H36B C51B H37B 109.5 . . ?
N3B C55 C56 114.3(11) . . ?
N3B C55 H50 108.7 . . ?
C56 C55 H50 108.7 . . ?
N3B C55 H51 108.7 . . ?
C56 C55 H51 108.7 . . ?
H50 C55 H51 107.6 . . ?
C55 C56 C51B 114.9(13) . . ?
C55 C56 H52 108.5 . . ?
C51B C56 H52 108.5 . . ?
C55 C56 H53 108.5 . . ?
C51B C56 H53 108.5 . . ?
H52 C56 H53 107.5 . . ?

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
C9 C4 C6 C15 -177.06(14) . . . . ?
C12 C4 C6 C15 1.2(2) . . . . ?
C9 C4 C6 C5 0.4(2) . . . . ?
C12 C4 C6 C5 178.73(14) . . . . ?
N1 C5 C6 C4 0.8(2) . . . . ?
C11 C5 C6 C4 -178.13(14) . . . . ?
N1 C5 C6 C15 178.31(14) . . . . ?
C11 C5 C6 C15 -0.6(2) . . . . ?
C11 C5 N1 C27 175.92(14) . . . . ?
C6 C5 N1 C27 -3.0(2) . . . . ?
C11 C5 N1 C18 -5.3(2) . . . . ?
C6 C5 N1 C18 175.79(13) . . . . ?
C6 C4 C9 C17 -179.53(14) . . . . ?
C12 C4 C9 C17 2.2(2) . . . . ?
C6 C4 C9 C27 0.3(2) . . . . ?
C12 C4 C9 C27 -177.96(14) . . . . ?
C17 N2 C10 C39 -172.93(15) . . . . ?
C14 N2 C10 C39 6.9(2) . . . . ?
C17 N2 C10 C12 6.3(2) . . . . ?
C14 N2 C10 C12 -173.87(14) . . . . ?
N1 C5 C11 C26 178.36(14) . . . . ?
C6 C5 C11 C26 -2.7(2) . . . . ?
C6 C4 C12 C35 -2.9(2) . . . . ?
C9 C4 C12 C35 175.37(14) . . . . ?
C6 C4 C12 C10 178.34(14) . . . . ?
C9 C4 C12 C10 -3.4(2) . . . . ?
N2 C10 C12 C4 -0.7(2) . . . . ?
C39 C10 C12 C4 178.53(15) . . . . ?
N2 C10 C12 C35 -179.48(14) . . . . ?
C39 C10 C12 C35 -0.2(2) . . . . ?
C17 N2 C14 C40 94.25(17) . . . . ?
C10 N2 C14 C40 -85.58(18) . . . . ?
C4 C6 C15 N3A 6.4(2) . . . . ?
C5 C6 C15 N3A -171.11(17) . . . . ?
C4 C6 C15 C24 -178.36(15) . . . . ?
C5 C6 C15 C24 4.1(2) . . . . ?
C4 C6 C15 N3B -17.9(6) . . . . ?
C5 C6 C15 N3B 164.6(6) . . . . ?
C29 C13 C16 C32 0.8(2) . . . . ?
B1 C13 C16 C32 -176.24(15) . . . . ?
C10 N2 C17 C28 172.77(15) . . . . ?
C14 N2 C17 C28 -7.1(2) . . . . ?
C10 N2 C17 C9 -7.5(2) . . . . ?
C14 N2 C17 C9 172.68(14) . . . . ?
C4 C9 C17 N2 3.1(2) . . . . ?
C27 C9 C17 N2 -176.74(13) . . . . ?
C4 C9 C17 C28 -177.14(14) . . . . ?
C27 C9 C17 C28 3.0(2) . . . . ?
C27 N1 C18 C48 -90.51(17) . . . . ?
C5 N1 C18 C48 90.68(18) . . . . ?
N3A C15 C24 C26 170.88(18) . . . . ?
C6 C15 C24 C26 -4.2(2) . . . . ?
N3B C15 C24 C26 -164.3(6) . . . . ?
C15 C24 C26 C11 0.8(3) . . . . ?
C5 C11 C26 C24 2.7(2) . . . . ?
C5 N1 C27 C25 -175.86(14) . . . . ?
C18 N1 C27 C25 5.4(2) . . . . ?
C5 N1 C27 C9 3.8(2) . . . . ?
C18 N1 C27 C9 -175.02(13) . . . . ?
C30 C25 C27 N1 -179.02(14) . . . . ?
C30 C25 C27 C9 1.4(2) . . . . ?
C4 C9 C27 N1 -2.4(2) . . . . ?
C17 C9 C27 N1 177.49(13) . . . . ?
C4 C9 C27 C25 177.27(14) . . . . ?
C17 C9 C27 C25 -2.9(2) . . . . ?
N2 C17 C28 C30 178.12(14) . . . . ?
C9 C17 C28 C30 -1.6(2) . . . . ?
C16 C13 C29 C31 -0.7(2) . . . . ?
B1 C13 C29 C31 176.39(15) . . . . ?
C27 C25 C30 C28 0.0(2) . . . . ?
C17 C28 C30 C25 0.1(2) . . . . ?
C13 C29 C31 C38 0.3(2) . . . . ?
C13 C16 C32 C38 -0.6(2) . . . . ?
C44 C23 C33 N5 -0.54(19) . . . . ?
C44 C23 C33 C36 174.02(17) . . . . ?
C35 C20 C34 C39 -0.5(3) . . . . ?
C34 C20 C35 N3A -175.23(19) . . . . ?
C34 C20 C35 C12 0.2(3) . . . . ?
C34 C20 C35 N3B 159.6(6) . . . . ?
C4 C12 C35 N3A -3.0(3) . . . . ?
C10 C12 C35 N3A 175.73(17) . . . . ?
C4 C12 C35 C20 -178.64(15) . . . . ?
C10 C12 C35 C20 0.1(2) . . . . ?
C4 C12 C35 N3B 21.7(7) . . . . ?
C10 C12 C35 N3B -159.6(6) . . . . ?
B1 O2 C36 C42 14.7(2) . . . . ?
B1 O2 C36 C33 -163.99(14) . . . . ?
N5 C33 C36 O2 -179.75(14) . . . . ?
C23 C33 C36 O2 6.4(3) . . . . ?
N5 C33 C36 C42 1.6(3) . . . . ?
C23 C33 C36 C42 -172.24(17) . . . . ?
C23 C33 N5 C46 -0.08(19) . . . . ?
C36 C33 N5 C46 -175.09(16) . . . . ?
C29 C31 C38 C32 0.0(2) . . . . ?
C16 C32 C38 C31 0.1(2) . . . . ?
C20 C34 C39 C10 0.4(3) . . . . ?
N2 C10 C39 C34 179.23(16) . . . . ?
C12 C10 C39 C34 0.0(3) . . . . ?
N2 C14 C40 C54 168.03(14) . . . . ?
C45 N4 C41 C19 -0.17(18) . . . . ?
C45 N4 C41 C43 175.91(15) . . . . ?
C47 C19 C41 N4 0.24(18) . . . . ?
C47 C19 C41 C43 -175.50(16) . . . . ?
O2 C36 C42 C43 2.7(2) . . . . ?
C33 C36 C42 C43 -178.75(15) . . . . ?
B1 O1 C43 C42 -12.1(2) . . . . ?
B1 O1 C43 C41 166.95(13) . . . . ?
C36 C42 C43 O1 -3.9(2) . . . . ?
C36 C42 C43 C41 177.06(14) . . . . ?
N4 C41 C43 O1 177.45(14) . . . . ?
C19 C41 C43 O1 -7.4(2) . . . . ?
N4 C41 C43 C42 -3.5(2) . . . . ?
C19 C41 C43 C42 171.65(16) . . . . ?
C33 C23 C44 C46 0.9(2) . . . . ?
C41 N4 C45 C47 0.03(19) . . . . ?
C33 N5 C46 C44 0.7(2) . . . . ?
C23 C44 C46 N5 -1.0(2) . . . . ?
N4 C45 C47 C19 0.1(2) . . . . ?
C41 C19 C47 C45 -0.22(19) . . . . ?
N1 C18 C48 C52 -179.12(15) . . . . ?
C36 O2 B1 F1 -141.91(14) . . . . ?
C36 O2 B1 O1 -27.35(19) . . . . ?
C36 O2 B1 C13 94.01(17) . . . . ?
C43 O1 B1 F1 141.59(13) . . . . ?
C43 O1 B1 O2 26.15(19) . . . . ?
C43 O1 B1 C13 -95.93(15) . . . . ?
C16 C13 B1 F1 -157.29(15) . . . . ?
C29 C13 B1 F1 25.7(2) . . . . ?
C16 C13 B1 O2 -36.6(2) . . . . ?
C29 C13 B1 O2 146.39(15) . . . . ?
C16 C13 B1 O1 84.65(18) . . . . ?
C29 C13 B1 O1 -92.32(17) . . . . ?
C24 C15 N3A C35 172.14(18) . . . . ?
C6 C15 N3A C35 -12.7(3) . . . . ?
N3B C15 N3A C35 81.2(17) . . . . ?
C24 C15 N3A C49 -11.4(3) . . . . ?
C6 C15 N3A C49 163.76(17) . . . . ?
N3B C15 N3A C49 -102.3(17) . . . . ?
C20 C35 N3A C15 -173.47(19) . . . . ?
C12 C35 N3A C15 11.0(3) . . . . ?
N3B C35 N3A C15 -83.2(16) . . . . ?
C20 C35 N3A C49 10.0(3) . . . . ?
C12 C35 N3A C49 -165.45(17) . . . . ?
N3B C35 N3A C49 100.3(17) . . . . ?
C15 N3A C49 C53 91.6(2) . . . . ?
C35 N3A C49 C53 -91.8(2) . . . . ?
N3A C49 C53 C51A -177.8(2) . . . . ?
N3A C35 N3B C55 -97.8(19) . . . . ?
C20 C35 N3B C55 5.1(13) . . . . ?
C12 C35 N3B C55 164.6(8) . . . . ?
N3A C35 N3B C15 60.7(13) . . . . ?
C20 C35 N3B C15 163.5(5) . . . . ?
C12 C35 N3B C15 -36.9(11) . . . . ?
N3A C15 N3B C55 95.6(19) . . . . ?
C24 C15 N3B C55 -6.3(13) . . . . ?
C6 C15 N3B C55 -166.7(8) . . . . ?
N3A C15 N3B C35 -62.6(14) . . . . ?
C24 C15 N3B C35 -164.5(5) . . . . ?
C6 C15 N3B C35 35.2(11) . . . . ?
C35 N3B C55 C56 80.2(13) . . . . ?
C15 N3B C55 C56 -76.5(14) . . . . ?
N3B C55 C56 C51B -179.7(14) . . . . ?

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
N4 H9 Cl3 0.88 2.62 3.4920(16) 169.9 .
N5 H21 Cl3 0.88 2.35 3.2227(17) 174.8 .

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        65.99
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.879
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 2086725'
loop_
_audit_author_name
_audit_author_address
'Nobuhiro Yasuda'
;Japan Synchrotron Radiation Research Institute
Japan
;
_audit_update_record             
;
2021-05-29 deposited with the CCDC.	2021-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 B N2 O4, C3 H6 O'
_chemical_formula_sum            'C21 H19 B N2 O5'
_chemical_formula_weight         390.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0045 0.0022 '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 0.0022 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0085 0.0044 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0146 0.0081 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           31
_space_group_name_H-M_alt        'P m n 21'
_space_group_name_Hall           'P 2ac -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.
;

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

_cell_length_a                   14.507(3)
_cell_length_b                   9.3436(17)
_cell_length_c                   14.134(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1915.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    95(2)
_cell_measurement_reflns_used    23414
_cell_measurement_theta_min      2.294
_cell_measurement_theta_max      31.773

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.129
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.631
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      95(2)
_diffrn_radiation_wavelength     0.8104
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'synchrotron radiation SPring-8 BL40XU'
_diffrn_radiation_monochromator  'Si(111) Channel Cut'
_diffrn_measurement_device_type  'DECTRIS EIGER X 1M'
_diffrn_measurement_method       'Shutterless ω scans'
_diffrn_detector_area_resol_mean 13.33
_diffrn_reflns_number            23414
_diffrn_reflns_av_unetI/netI     0.0828
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.294
_diffrn_reflns_theta_max         31.773
_diffrn_reflns_theta_full        29.094
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             4402
_reflns_number_gt                3889
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_max     0.926
_reflns_Friedel_fraction_full    0.968

_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       'Rapid Auto(Rigaku)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0654P)²+0.0129P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1527 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4402
_refine_ls_number_parameters     298
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1302
_refine_ls_wR_factor_gt          0.1230
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
C1 C 0.1759(2) 0.2470(3) 0.4690(2) 0.0364(7) Uani 1 1 d . . . . .
H1 H 0.1130 0.2741 0.4745 0.044 Uiso 1 1 calc R U . . .
C2 C 0.20743(19) 0.1152(3) 0.4397(2) 0.0398(6) Uani 1 1 d . . . . .
H2 H 0.1705 0.0361 0.4212 0.048 Uiso 1 1 calc R U . . .
C3 C 0.30432(19) 0.1191(3) 0.4421(2) 0.0344(6) Uani 1 1 d . . . . .
H3 H 0.3449 0.0434 0.4254 0.041 Uiso 1 1 calc R U . . .
C4 C 0.32942(18) 0.2546(3) 0.4734(2) 0.0297(6) Uani 1 1 d . . . . .
C5 C 0.41769(17) 0.3188(3) 0.4875(2) 0.0298(5) Uani 1 1 d . . . . .
C6 C 0.5000 0.2440(4) 0.4829(3) 0.0309(8) Uani 1 2 d S T P . .
H6 H 0.5000 0.1428 0.4765 0.037 Uiso 1 2 calc R U P . .
C7 C 0.5000 0.6299(4) 0.6185(3) 0.0343(9) Uani 1 2 d S T P . .
C8 C 0.5000 0.5949(5) 0.7142(4) 0.0407(9) Uani 1 2 d S T P . .
H8 H 0.5000 0.4975 0.7333 0.049 Uiso 1 2 calc R U P . .
C9 C 0.5000 0.7030(5) 0.7817(3) 0.0454(10) Uani 1 2 d S T P . .
H9 H 0.5000 0.6783 0.8469 0.054 Uiso 1 2 calc R U P . .
C10 C 0.5000 0.8464(5) 0.7559(3) 0.0416(10) Uani 1 2 d S T P . .
H10 H 0.5000 0.9189 0.8031 0.050 Uiso 1 2 calc R U P . .
C11 C 0.5000 0.8831(4) 0.6612(3) 0.0352(9) Uani 1 2 d S T P . .
H11 H 0.5000 0.9806 0.6423 0.042 Uiso 1 2 calc R U P . .
C12 C 0.5000 0.7748(4) 0.5949(3) 0.0295(8) Uani 1 2 d S T P . .
C13 C 0.5000 0.7906(4) 0.4901(3) 0.0298(8) Uani 1 2 d S T P . .
N1 N 0.24924(14) 0.3315(3) 0.48867(18) 0.0303(5) Uani 1 1 d . . . . .
H1A H 0.2464 0.4208 0.5081 0.036 Uiso 1 1 calc R U . . .
O1 O 0.41565(12) 0.45693(19) 0.50576(18) 0.0421(5) Uani 1 1 d . . . . .
O2 O 0.5000 0.6606(3) 0.4497(2) 0.0319(6) Uani 1 2 d S T P . .
O3 O 0.5000 0.8998(3) 0.4445(2) 0.0355(6) Uani 1 2 d S T P . .
C14 C 0.32461(19) 0.7595(3) 0.3025(2) 0.0335(6) Uani 1 1 d . . . . .
H14 H 0.3874 0.7491 0.3204 0.040 Uiso 1 1 calc R U . . .
C15 C 0.29315(18) 0.8169(3) 0.2181(2) 0.0340(6) Uani 1 1 d . . . . .
H15 H 0.3302 0.8515 0.1677 0.041 Uiso 1 1 calc R U . . .
C16 C 0.19679(18) 0.8143(3) 0.2207(2) 0.0315(6) Uani 1 1 d . . . . .
H16 H 0.1563 0.8477 0.1728 0.038 Uiso 1 1 calc R U . . .
C17 C 0.17131(17) 0.7535(3) 0.3072(2) 0.0287(6) Uani 1 1 d . . . . .
C18 C 0.08299(17) 0.7197(3) 0.3457(2) 0.0293(6) Uani 1 1 d . . . . .
C19 C 0.0000 0.7694(4) 0.3090(3) 0.0305(8) Uani 1 2 d S T P . .
H19 H 0.0000 0.8373 0.2590 0.037 Uiso 1 2 calc R U P . .
C20 C 0.0000 0.7410(4) 0.5645(3) 0.0350(9) Uani 1 2 d S T P . .
C21 C 0.0000 0.8906(5) 0.5710(4) 0.0409(10) Uani 1 2 d S T P . .
H21 H 0.0000 0.9471 0.5151 0.049 Uiso 1 2 calc R U P . .
C22 C 0.0000 0.9563(5) 0.6591(4) 0.0484(11) Uani 1 2 d S T P . .
H22 H 0.0000 1.0577 0.6635 0.058 Uiso 1 2 calc R U P . .
C23 C 0.0000 0.8726(6) 0.7422(3) 0.0525(13) Uani 1 2 d S T P . .
H23 H 0.0000 0.9182 0.8022 0.063 Uiso 1 2 calc R U P . .
C24 C 0.0000 0.7226(6) 0.7370(3) 0.0465(11) Uani 1 2 d S T P . .
H24 H 0.0000 0.6652 0.7925 0.056 Uiso 1 2 calc R U P . .
C25 C 0.0000 0.6617(5) 0.6476(3) 0.0379(9) Uani 1 2 d S T P . .
C26 C 0.0000 0.5058(5) 0.6246(3) 0.0378(9) Uani 1 2 d S T P . .
N2 N 0.25105(13) 0.7209(3) 0.35507(18) 0.0298(5) Uani 1 1 d . . . . .
H2A H 0.2537 0.6809 0.4114 0.036 Uiso 1 1 calc R U . . .
C27 C 0.24973(19) 0.8322(3) 0.6492(3) 0.0388(7) Uani 1 1 d . . . . .
H27 H 0.2602 0.8808 0.5887 0.058 Uiso 1 1 calc R U . . .
H27A H 0.3003 0.8546 0.6927 0.058 Uiso 1 1 calc R U . . .
H27B H 0.1914 0.8650 0.6766 0.058 Uiso 1 1 calc R U . . .
B1 B 0.0000 0.6274(5) 0.4799(3) 0.0301(9) Uani 1 2 d S T P . .
B2 B 0.5000 0.5441(4) 0.5212(4) 0.0369(10) Uani 1 2 d S T P . .
O4 O 0.08388(12) 0.6326(2) 0.41952(14) 0.0327(4) Uani 1 1 d . . . . .
O5 O 0.0000 0.4876(3) 0.5305(2) 0.0359(6) Uani 1 2 d S T P . .
O6 O 0.0000 0.4060(4) 0.6796(2) 0.0513(8) Uani 1 2 d S T P . .
C28 C 0.24566(15) 0.6740(3) 0.6335(2) 0.0296(6) Uani 1 1 d . . . . .
C29 C 0.24082(19) 0.5809(3) 0.7198(2) 0.0377(6) Uani 1 1 d . . . . .
H29 H 0.2359 0.4804 0.7005 0.057 Uiso 1 1 calc R U . . .
H29A H 0.1867 0.6072 0.7574 0.057 Uiso 1 1 calc R U . . .
H29B H 0.2967 0.5941 0.7578 0.057 Uiso 1 1 calc R U . . .
O7 O 0.24616(11) 0.6227(2) 0.55406(17) 0.0335(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
C1 N1 1.354(3) . ?
C1 C2 1.377(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.406(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(4) . ?
C3 H3 0.9500 . ?
C4 N1 1.384(3) . ?
C4 C5 1.428(4) . ?
C5 O1 1.317(3) . ?
C5 C6 1.385(3) . ?
C6 C5 1.385(3) 3_655 ?
C6 H6 0.9500 . ?
C7 C8 1.391(7) . ?
C7 C12 1.394(5) . ?
C7 B2 1.592(7) . ?
C8 C9 1.390(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.489(5) . ?
C13 O3 1.207(4) . ?
C13 O2 1.343(4) . ?
N1 H1A 0.8800 . ?
O1 B2 1.486(3) . ?
O2 B2 1.485(6) . ?
C14 N2 1.349(4) . ?
C14 C15 1.385(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.399(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.397(4) . ?
C16 H16 0.9500 . ?
C17 N2 1.375(4) . ?
C17 C18 1.427(4) . ?
C18 O4 1.324(3) . ?
C18 C19 1.390(3) . ?
C19 C18 1.390(3) 3 ?
C19 H19 0.9500 . ?
C20 C25 1.389(6) . ?
C20 C21 1.401(6) . ?
C20 B1 1.599(6) . ?
C21 C22 1.389(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.410(8) . ?
C22 H22 0.9500 . ?
C23 C24 1.404(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.493(6) . ?
C26 O6 1.215(5) . ?
C26 O5 1.341(5) . ?
N2 H2A 0.8800 . ?
C27 C28 1.496(4) . ?
C27 H27 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
B1 O4 1.487(3) . ?
B1 O4 1.487(3) 3 ?
B1 O5 1.489(5) . ?
B2 O1 1.486(3) 3_655 ?
C28 O7 1.221(4) . ?
C28 C29 1.500(5) . ?
C29 H29 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 108.8(2) . . ?
N1 C1 H1 125.6 . . ?
C2 C1 H1 125.6 . . ?
C1 C2 C3 107.5(2) . . ?
C1 C2 H2 126.2 . . ?
C3 C2 H2 126.2 . . ?
C4 C3 C2 107.1(2) . . ?
C4 C3 H3 126.5 . . ?
C2 C3 H3 126.5 . . ?
N1 C4 C3 107.6(2) . . ?
N1 C4 C5 120.9(2) . . ?
C3 C4 C5 131.4(3) . . ?
O1 C5 C6 121.5(2) . . ?
O1 C5 C4 114.8(2) . . ?
C6 C5 C4 123.7(2) . . ?
C5 C6 C5 119.1(3) 3_655 . ?
C5 C6 H6 120.4 3_655 . ?
C5 C6 H6 120.4 . . ?
C8 C7 C12 117.4(4) . . ?
C8 C7 B2 136.2(4) . . ?
C12 C7 B2 106.4(3) . . ?
C9 C8 C7 119.8(4) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 121.4(4) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C11 C10 C9 119.6(4) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C10 118.4(4) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C11 C12 C7 123.3(4) . . ?
C11 C12 C13 127.1(4) . . ?
C7 C12 C13 109.5(3) . . ?
O3 C13 O2 122.5(3) . . ?
O3 C13 C12 128.0(4) . . ?
O2 C13 C12 109.5(3) . . ?
C1 N1 C4 109.0(2) . . ?
C1 N1 H1A 125.5 . . ?
C4 N1 H1A 125.5 . . ?
C5 O1 B2 123.2(2) . . ?
C13 O2 B2 111.9(3) . . ?
N2 C14 C15 108.5(2) . . ?
N2 C14 H14 125.8 . . ?
C15 C14 H14 125.8 . . ?
C14 C15 C16 107.5(2) . . ?
C14 C15 H15 126.3 . . ?
C16 C15 H15 126.3 . . ?
C17 C16 C15 107.1(2) . . ?
C17 C16 H16 126.4 . . ?
C15 C16 H16 126.4 . . ?
N2 C17 C16 107.3(2) . . ?
N2 C17 C18 121.2(3) . . ?
C16 C17 C18 131.4(3) . . ?
O4 C18 C19 120.5(2) . . ?
O4 C18 C17 115.3(2) . . ?
C19 C18 C17 124.1(3) . . ?
C18 C19 C18 120.0(4) 3 . ?
C18 C19 H19 120.0 3 . ?
C18 C19 H19 120.0 . . ?
C25 C20 C21 118.4(4) . . ?
C25 C20 B1 106.1(4) . . ?
C21 C20 B1 135.4(4) . . ?
C22 C21 C20 120.0(5) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.1(4) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 120.7(4) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 117.2(5) . . ?
C25 C24 H24 121.4 . . ?
C23 C24 H24 121.4 . . ?
C24 C25 C20 123.5(4) . . ?
C24 C25 C26 126.8(4) . . ?
C20 C25 C26 109.6(4) . . ?
O6 C26 O5 122.5(4) . . ?
O6 C26 C25 127.6(4) . . ?
O5 C26 C25 109.9(3) . . ?
C14 N2 C17 109.6(3) . . ?
C14 N2 H2A 125.2 . . ?
C17 N2 H2A 125.2 . . ?
C28 C27 H27 109.5 . . ?
C28 C27 H27A 109.5 . . ?
H27 C27 H27A 109.5 . . ?
C28 C27 H27B 109.5 . . ?
H27 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O4 B1 O4 109.8(3) . 3 ?
O4 B1 O5 107.7(2) . . ?
O4 B1 O5 107.7(2) 3 . ?
O4 B1 C20 114.0(2) . . ?
O4 B1 C20 114.0(2) 3 . ?
O5 B1 C20 102.9(3) . . ?
O2 B2 O1 107.5(3) . . ?
O2 B2 O1 107.6(3) . 3_655 ?
O1 B2 O1 110.8(3) . 3_655 ?
O2 B2 C7 102.7(3) . . ?
O1 B2 C7 113.8(2) . . ?
O1 B2 C7 113.8(2) 3_655 . ?
C18 O4 B1 117.7(2) . . ?
C26 O5 B1 111.4(3) . . ?
O7 C28 C27 121.6(3) . . ?
O7 C28 C29 121.3(2) . . ?
C27 C28 C29 117.0(3) . . ?
C28 C29 H29 109.5 . . ?
C28 C29 H29A 109.5 . . ?
H29 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.4(4) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 N1 -0.6(3) . . . . ?
C2 C3 C4 C5 -178.7(3) . . . . ?
N1 C4 C5 O1 -6.8(4) . . . . ?
C3 C4 C5 O1 171.1(3) . . . . ?
N1 C4 C5 C6 173.2(3) . . . . ?
C3 C4 C5 C6 -9.0(5) . . . . ?
O1 C5 C6 C5 -6.9(6) . . . 3_655 ?
C4 C5 C6 C5 173.1(2) . . . 3_655 ?
C12 C7 C8 C9 0.000(3) . . . . ?
B2 C7 C8 C9 180.000(2) . . . . ?
C7 C8 C9 C10 0.000(3) . . . . ?
C8 C9 C10 C11 0.000(3) . . . . ?
C9 C10 C11 C12 0.000(2) . . . . ?
C10 C11 C12 C7 0.000(2) . . . . ?
C10 C11 C12 C13 180.000(2) . . . . ?
C8 C7 C12 C11 0.000(2) . . . . ?
B2 C7 C12 C11 180.000(2) . . . . ?
C8 C7 C12 C13 180.000(2) . . . . ?
B2 C7 C12 C13 0.000(1) . . . . ?
C11 C12 C13 O3 0.000(2) . . . . ?
C7 C12 C13 O3 180.000(1) . . . . ?
C11 C12 C13 O2 180.000(2) . . . . ?
C7 C12 C13 O2 0.000(2) . . . . ?
C2 C1 N1 C4 -0.7(4) . . . . ?
C3 C4 N1 C1 0.8(4) . . . . ?
C5 C4 N1 C1 179.1(2) . . . . ?
C6 C5 O1 B2 1.0(5) . . . . ?
C4 C5 O1 B2 -179.0(3) . . . . ?
O3 C13 O2 B2 180.000(2) . . . . ?
C12 C13 O2 B2 0.000(2) . . . . ?
N2 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C17 -0.6(3) . . . . ?
C15 C16 C17 N2 0.1(3) . . . . ?
C15 C16 C17 C18 -177.2(3) . . . . ?
N2 C17 C18 O4 -12.3(4) . . . . ?
C16 C17 C18 O4 164.7(3) . . . . ?
N2 C17 C18 C19 169.2(3) . . . . ?
C16 C17 C18 C19 -13.8(5) . . . . ?
O4 C18 C19 C18 -4.6(5) . . . 3 ?
C17 C18 C19 C18 173.8(2) . . . 3 ?
C25 C20 C21 C22 0.000(3) . . . . ?
B1 C20 C21 C22 180.000(3) . . . . ?
C20 C21 C22 C23 0.000(3) . . . . ?
C21 C22 C23 C24 0.000(3) . . . . ?
C22 C23 C24 C25 0.000(3) . . . . ?
C23 C24 C25 C20 0.000(3) . . . . ?
C23 C24 C25 C26 180.000(2) . . . . ?
C21 C20 C25 C24 0.000(3) . . . . ?
B1 C20 C25 C24 180.000(2) . . . . ?
C21 C20 C25 C26 180.000(2) . . . . ?
B1 C20 C25 C26 0.000(2) . . . . ?
C24 C25 C26 O6 0.000(3) . . . . ?
C20 C25 C26 O6 180.000(2) . . . . ?
C24 C25 C26 O5 180.000(2) . . . . ?
C20 C25 C26 O5 0.000(2) . . . . ?
C15 C14 N2 C17 -0.8(3) . . . . ?
C16 C17 N2 C14 0.4(3) . . . . ?
C18 C17 N2 C14 178.0(2) . . . . ?
C25 C20 B1 O4 -116.4(3) . . . . ?
C21 C20 B1 O4 63.6(3) . . . . ?
C25 C20 B1 O4 116.4(3) . . . 3 ?
C21 C20 B1 O4 -63.6(3) . . . 3 ?
C25 C20 B1 O5 0.000(1) . . . . ?
C21 C20 B1 O5 180.000(2) . . . . ?
C13 O2 B2 O1 120.3(2) . . . . ?
C13 O2 B2 O1 -120.3(2) . . . 3_655 ?
C13 O2 B2 C7 0.000(1) . . . . ?
C5 O1 B2 O2 121.7(3) . . . . ?
C5 O1 B2 O1 4.4(5) . . . 3_655 ?
C5 O1 B2 C7 -125.3(3) . . . . ?
C8 C7 B2 O2 180.000(2) . . . . ?
C12 C7 B2 O2 0.000(1) . . . . ?
C8 C7 B2 O1 64.1(3) . . . . ?
C12 C7 B2 O1 -115.9(3) . . . . ?
C8 C7 B2 O1 -64.1(3) . . . 3_655 ?
C12 C7 B2 O1 115.9(3) . . . 3_655 ?
C19 C18 O4 B1 -19.4(4) . . . . ?
C17 C18 O4 B1 162.1(3) . . . . ?
O4 B1 O4 C18 40.0(4) 3 . . . ?
O5 B1 O4 C18 157.0(2) . . . . ?
C20 B1 O4 C18 -89.4(3) . . . . ?
O6 C26 O5 B1 180.000(2) . . . . ?
C25 C26 O5 B1 0.000(2) . . . . ?
O4 B1 O5 C26 120.8(2) . . . . ?
O4 B1 O5 C26 -120.8(2) 3 . . . ?
C20 B1 O5 C26 0.000(2) . . . . ?

_refine_diff_density_max         0.477
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.141



