# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_a20190212_bodipv
_database_code_depnum_ccdc_archive 'CCDC 2177585'
loop_
_audit_author_name
_audit_author_address
'Leire San Felices'
;Universidad el Pais Vasco
Spain
;
_audit_update_record             
;
2022-06-07 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;

_audit_creation_date             2022-05-11T15:44:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C22 H27 B N4 O2'
_chemical_formula_sum            'C22 H27 B N4 O2'
_chemical_formula_weight         390.28

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_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                   9.5191(6)
_cell_length_b                   10.8959(7)
_cell_length_c                   11.6708(6)
_cell_angle_alpha                114.490(5)
_cell_angle_beta                 96.844(5)
_cell_angle_gamma                101.099(5)
_cell_volume                     1053.80(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    2418
_cell_measurement_theta_min      4.241
_cell_measurement_theta_max      73.019

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.299
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.043
_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.23
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -4 7 0.0164
-1 4 -7 0.0263
0 -1 0 0.0248
-1 2 -7 0.0192
0 1 0 0.0216
2 0 -1 0.1373
-3 1 0 0.1453


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
        model based on expressions derived by R.C. Clark & J.S. Reid.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.978

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_source_voltage           50
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 5.2012
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.1104466
_diffrn_orient_matrix_ub_12      -0.1458528
_diffrn_orient_matrix_ub_13      -0.0691029
_diffrn_orient_matrix_ub_21      0.1237915
_diffrn_orient_matrix_ub_22      -0.0655994
_diffrn_orient_matrix_ub_23      -0.0490833
_diffrn_orient_matrix_ub_31      0.03314
_diffrn_orient_matrix_ub_32      -0.0206505
_diffrn_orient_matrix_ub_33      0.1222895
_diffrn_measurement_device       'four-circleκ-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0816
_diffrn_reflns_number            6898
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.27
_diffrn_reflns_theta_max         68.97
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             3908
_reflns_number_gt                2860
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00  34.00   1.00    2.00    --  -42.13  77.00 150.00  102
  2  ω    -68.00  34.00   1.00    2.00    --  -42.13  77.00 -90.00  102
  3  ω    -70.00  25.00   1.00    2.00    --  -42.13  57.00  60.00   95
  4  ω     37.00  74.00   1.00   10.00    --  107.93 -46.00 -39.00   37
  5  ω     91.00 117.00   1.00   10.00    --  107.93-125.00-180.00   26
  6  ω     38.00  64.00   1.00   10.00    --  107.93 -30.00  30.00   26
  7  ω     37.00  66.00   1.00   10.00    --  107.93 -30.00 120.00   29
  8  ω     26.00 154.00   1.00   10.00    --  107.93 -15.00 150.00  128
  9  ω     34.00 104.00   1.00   10.00    --  107.93 -94.00   0.00   70
 10  ω     33.00  63.00   1.00   10.00    --  107.93 -30.00  90.00   30
 11  ω     77.00 115.00   1.00   10.00    --  107.93-125.00 -30.00   38
 12  ω     38.00 141.00   1.00   10.00    --  107.93 -77.00  60.00  103
 13  ω     32.00  69.00   1.00   10.00    --  107.93 -30.00 -30.00   37
 14  ω     82.00 108.00   1.00   10.00    --  107.93-125.00-120.00   26
 15  ω     81.00 156.00   1.00   10.00    --  107.93  61.00 -30.00   75
 16  ω     39.00  68.00   1.00   10.00    --  107.93 -30.00   0.00   29
 17  ω     46.00  77.00   1.00   10.00    --  107.93 -45.00  60.00   31
 18  ω     37.00 134.00   1.00   10.00    --  107.93 -61.00-180.00   97
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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.
 shelx_SHELXL_version_number            2018/3
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0586P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3908
_refine_ls_number_parameters     269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.049
_refine_ls_wR_factor_ref         0.1292
_refine_ls_wR_factor_gt          0.1179
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.048

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.009 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.08231(15) 0.87688(15) 0.84612(14) 0.0300(3) Uani 1 1 d . . . . .
O2 O 0.27918(17) 0.80473(17) 0.89095(15) 0.0407(4) Uani 1 1 d . . . . .
N1 N -0.23540(16) 0.65324(16) 0.70637(14) 0.0216(3) Uani 1 1 d . . . . .
N2 N -0.36252(16) 0.49006(16) 0.78363(15) 0.0225(3) Uani 1 1 d . . . . .
N3 N -0.0231(2) 0.7028(2) 1.00328(18) 0.0366(4) Uani 1 1 d . . . . .
N4 N -0.11298(19) 0.3443(2) 0.59505(18) 0.0350(4) Uani 1 1 d . . . . .
C1 C -0.1296(2) 0.73358(19) 0.67941(17) 0.0233(4) Uani 1 1 d . . . . .
C2 C -0.1938(2) 0.7998(2) 0.61585(17) 0.0255(4) Uani 1 1 d . . . . .
C3 C -0.3457(2) 0.75856(19) 0.60434(17) 0.0253(4) Uani 1 1 d . . . . .
C4 C -0.37138(19) 0.66531(19) 0.66027(17) 0.0220(4) Uani 1 1 d . . . . .
C5 C -0.50184(19) 0.59259(19) 0.67679(17) 0.0225(4) Uani 1 1 d . . . . .
C6 C -0.49664(19) 0.51061(19) 0.74099(17) 0.0225(4) Uani 1 1 d . . . . .
C7 C -0.6084(2) 0.4316(2) 0.77463(18) 0.0257(4) Uani 1 1 d . . . . .
C8 C -0.5401(2) 0.3648(2) 0.83392(19) 0.0274(4) Uani 1 1 d . . . . .
C9 C -0.3884(2) 0.4027(2) 0.83715(18) 0.0257(4) Uani 1 1 d . . . . .
C10 C 0.0307(2) 0.7520(2) 0.72182(19) 0.0267(4) Uani 1 1 d . . . . .
H10A H 0.046977 0.669115 0.730944 0.032 Uiso 1 1 calc R . . . .
H10B H 0.084106 0.763959 0.657764 0.032 Uiso 1 1 calc R . . . .
C11 C 0.2074(2) 0.8891(2) 0.9219(2) 0.0307(4) Uani 1 1 d . . . . .
C12 C 0.2446(3) 1.0181(3) 1.0473(2) 0.0444(6) Uani 1 1 d . . . . .
H12A H 0.210276 1.091579 1.034341 0.067 Uiso 1 1 calc GR . . . .
H12B H 0.351189 1.049987 1.080652 0.067 Uiso 1 1 calc GR . . . .
H12C H 0.196579 0.997433 1.109519 0.067 Uiso 1 1 calc GR . . . .
C13 C -0.1121(2) 0.9031(2) 0.5769(2) 0.0317(4) Uani 1 1 d . . . . .
H13A H -0.169959 0.891921 0.495241 0.038 Uiso 1 1 calc R . . . .
H13B H -0.017414 0.88265 0.56088 0.038 Uiso 1 1 calc R . . . .
C14 C -0.0826(4) 1.0541(3) 0.6797(3) 0.0520(7) Uani 1 1 d . . . . .
H14A H -0.03314 1.117735 0.648394 0.078 Uiso 1 1 calc GR . . . .
H14B H -0.019841 1.067334 0.759046 0.078 Uiso 1 1 calc GR . . . .
H14C H -0.175865 1.074197 0.69745 0.078 Uiso 1 1 calc GR . . . .
C15 C -0.4532(2) 0.8131(2) 0.5458(2) 0.0335(5) Uani 1 1 d . . . . .
H15A H -0.514999 0.736709 0.464618 0.05 Uiso 1 1 calc GR . . . .
H15B H -0.399419 0.887607 0.528659 0.05 Uiso 1 1 calc GR . . . .
H15C H -0.51521 0.850319 0.605915 0.05 Uiso 1 1 calc GR . . . .
C16 C -0.6469(2) 0.6042(2) 0.6222(2) 0.0309(4) Uani 1 1 d . . . . .
H16A H -0.67742 0.676888 0.689886 0.046 Uiso 1 1 calc GR . . . .
H16B H -0.720791 0.514328 0.589722 0.046 Uiso 1 1 calc GR . . . .
H16C H -0.637345 0.628932 0.5512 0.046 Uiso 1 1 calc GR . . . .
C17 C -0.7692(2) 0.4222(2) 0.7546(2) 0.0341(5) Uani 1 1 d . . . . .
H17A H -0.782943 0.516702 0.789405 0.051 Uiso 1 1 calc GR . . . .
H17B H -0.815361 0.372103 0.799196 0.051 Uiso 1 1 calc GR . . . .
H17C H -0.814384 0.371682 0.662008 0.051 Uiso 1 1 calc GR . . . .
C18 C -0.6088(2) 0.2630(2) 0.8806(2) 0.0358(5) Uani 1 1 d . . . . .
H18A H -0.70296 0.280313 0.901842 0.043 Uiso 1 1 calc R . . . .
H18B H -0.543019 0.278007 0.960327 0.043 Uiso 1 1 calc R . . . .
C19 C -0.6364(4) 0.1123(3) 0.7788(3) 0.0554(7) Uani 1 1 d . . . . .
H19A H -0.704755 0.096181 0.701112 0.083 Uiso 1 1 calc GR . . . .
H19B H -0.67872 0.048489 0.812696 0.083 Uiso 1 1 calc GR . . . .
H19C H -0.543327 0.095243 0.757144 0.083 Uiso 1 1 calc GR . . . .
C20 C -0.2709(2) 0.3545(2) 0.8894(2) 0.0335(5) Uani 1 1 d . . . . .
H20A H -0.225851 0.302646 0.819645 0.05 Uiso 1 1 calc GR . . . .
H20B H -0.313692 0.293419 0.925771 0.05 Uiso 1 1 calc GR . . . .
H20C H -0.195852 0.435805 0.957072 0.05 Uiso 1 1 calc GR . . . .
C21 C -0.1000(2) 0.6399(2) 0.90365(18) 0.0253(4) Uani 1 1 d . . . . .
C22 C -0.15137(19) 0.4314(2) 0.66902(18) 0.0256(4) Uani 1 1 d . . . . .
B1 B -0.2134(2) 0.5544(2) 0.76532(19) 0.0215(4) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.461(2) . ?
O1 C11 1.345(3) . ?
O2 C11 1.212(3) . ?
N1 C1 1.358(3) . ?
N1 C4 1.393(2) . ?
N1 B1 1.531(3) . ?
N2 C6 1.407(2) . ?
N2 C9 1.341(3) . ?
N2 B1 1.538(2) . ?
N3 C21 1.141(3) . ?
N4 C22 1.144(3) . ?
C1 C2 1.397(3) . ?
C1 C10 1.495(3) . ?
C2 C3 1.401(3) . ?
C2 C13 1.499(3) . ?
C3 C4 1.418(3) . ?
C3 C15 1.508(3) . ?
C4 C5 1.418(3) . ?
C5 C6 1.387(3) . ?
C5 C16 1.502(2) . ?
C6 C7 1.434(3) . ?
C7 C8 1.386(3) . ?
C7 C17 1.497(3) . ?
C8 C9 1.415(3) . ?
C8 C18 1.504(3) . ?
C9 C20 1.493(3) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 C12 1.491(3) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C13 C14 1.527(3) . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
C18 C19 1.523(3) . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C21 B1 1.609(3) . ?
C22 B1 1.619(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C10 116.88(15) . . ?
C1 N1 C4 108.43(15) . . ?
C1 N1 B1 126.60(15) . . ?
C4 N1 B1 124.72(15) . . ?
C6 N2 B1 124.39(16) . . ?
C9 N2 C6 108.78(15) . . ?
C9 N2 B1 126.79(15) . . ?
N1 C1 C2 109.79(16) . . ?
N1 C1 C10 122.98(17) . . ?
C2 C1 C10 127.10(19) . . ?
C1 C2 C3 106.96(18) . . ?
C1 C2 C13 125.47(18) . . ?
C3 C2 C13 127.43(18) . . ?
C2 C3 C4 107.36(16) . . ?
C2 C3 C15 123.08(19) . . ?
C4 C3 C15 129.52(18) . . ?
N1 C4 C3 107.44(16) . . ?
N1 C4 C5 120.29(16) . . ?
C3 C4 C5 132.26(16) . . ?
C4 C5 C16 118.91(17) . . ?
C6 C5 C4 120.94(16) . . ?
C6 C5 C16 120.14(17) . . ?
N2 C6 C7 106.91(16) . . ?
C5 C6 N2 120.64(16) . . ?
C5 C6 C7 132.43(17) . . ?
C6 C7 C17 128.09(19) . . ?
C8 C7 C6 107.20(16) . . ?
C8 C7 C17 124.69(19) . . ?
C7 C8 C9 107.42(18) . . ?
C7 C8 C18 128.56(19) . . ?
C9 C8 C18 123.92(19) . . ?
N2 C9 C8 109.68(17) . . ?
N2 C9 C20 123.22(17) . . ?
C8 C9 C20 127.09(19) . . ?
O1 C10 C1 106.74(15) . . ?
O1 C10 H10A 110.4 . . ?
O1 C10 H10B 110.4 . . ?
C1 C10 H10A 110.4 . . ?
C1 C10 H10B 110.4 . . ?
H10A C10 H10B 108.6 . . ?
O1 C11 C12 111.38(18) . . ?
O2 C11 O1 123.58(19) . . ?
O2 C11 C12 125.0(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C13 H13A 109.1 . . ?
C2 C13 H13B 109.1 . . ?
C2 C13 C14 112.42(18) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C15 H15A 109.5 . . ?
C3 C15 H15B 109.5 . . ?
C3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C16 H16A 109.5 . . ?
C5 C16 H16B 109.5 . . ?
C5 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 C17 H17A 109.5 . . ?
C7 C17 H17B 109.5 . . ?
C7 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C8 C18 H18A 109.4 . . ?
C8 C18 H18B 109.4 . . ?
C8 C18 C19 111.31(19) . . ?
H18A C18 H18B 108 . . ?
C19 C18 H18A 109.4 . . ?
C19 C18 H18B 109.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C9 C20 H20A 109.5 . . ?
C9 C20 H20B 109.5 . . ?
C9 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 B1 177.7(2) . . ?
N4 C22 B1 176.00(19) . . ?
N1 B1 N2 108.43(14) . . ?
N1 B1 C21 110.08(15) . . ?
N1 B1 C22 109.56(15) . . ?
N2 B1 C21 109.06(15) . . ?
N2 B1 C22 109.68(15) . . ?
C21 B1 C22 110.00(14) . . ?

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(2) . . . . ?
N1 C1 C2 C13 176.45(17) . . . . ?
N1 C1 C10 O1 -92.4(2) . . . . ?
N1 C4 C5 C6 1.3(3) . . . . ?
N1 C4 C5 C16 -178.04(16) . . . . ?
N2 C6 C7 C8 -0.9(2) . . . . ?
N2 C6 C7 C17 177.73(18) . . . . ?
C1 N1 C4 C3 -0.68(19) . . . . ?
C1 N1 C4 C5 -179.42(16) . . . . ?
C1 N1 B1 N2 177.68(16) . . . . ?
C1 N1 B1 C21 58.5(2) . . . . ?
C1 N1 B1 C22 -62.6(2) . . . . ?
C1 C2 C3 C4 -0.8(2) . . . . ?
C1 C2 C3 C15 177.31(17) . . . . ?
C1 C2 C13 C14 -92.5(3) . . . . ?
C2 C1 C10 O1 83.1(2) . . . . ?
C2 C3 C4 N1 0.91(19) . . . . ?
C2 C3 C4 C5 179.45(18) . . . . ?
C3 C2 C13 C14 82.8(3) . . . . ?
C3 C4 C5 C6 -177.12(18) . . . . ?
C3 C4 C5 C16 3.6(3) . . . . ?
C4 N1 C1 C2 0.2(2) . . . . ?
C4 N1 C1 C10 176.43(16) . . . . ?
C4 N1 B1 N2 -8.6(2) . . . . ?
C4 N1 B1 C21 -127.86(17) . . . . ?
C4 N1 B1 C22 111.05(18) . . . . ?
C4 C5 C6 N2 -4.3(3) . . . . ?
C4 C5 C6 C7 177.49(18) . . . . ?
C5 C6 C7 C8 177.48(19) . . . . ?
C5 C6 C7 C17 -3.9(3) . . . . ?
C6 N2 C9 C8 -1.2(2) . . . . ?
C6 N2 C9 C20 178.17(18) . . . . ?
C6 N2 B1 N1 5.5(2) . . . . ?
C6 N2 B1 C21 125.34(17) . . . . ?
C6 N2 B1 C22 -114.14(18) . . . . ?
C6 C7 C8 C9 0.2(2) . . . . ?
C6 C7 C8 C18 -176.20(19) . . . . ?
C7 C8 C9 N2 0.6(2) . . . . ?
C7 C8 C9 C20 -178.71(19) . . . . ?
C7 C8 C18 C19 94.4(3) . . . . ?
C9 N2 C6 C5 -177.33(17) . . . . ?
C9 N2 C6 C7 1.27(19) . . . . ?
C9 N2 B1 N1 -177.17(17) . . . . ?
C9 N2 B1 C21 -57.3(2) . . . . ?
C9 N2 B1 C22 63.2(2) . . . . ?
C9 C8 C18 C19 -81.4(3) . . . . ?
C10 O1 C11 O2 1.7(3) . . . . ?
C10 O1 C11 C12 -177.88(18) . . . . ?
C10 C1 C2 C3 -175.66(17) . . . . ?
C10 C1 C2 C13 0.4(3) . . . . ?
C11 O1 C10 C1 159.05(17) . . . . ?
C13 C2 C3 C4 -176.76(18) . . . . ?
C13 C2 C3 C15 1.3(3) . . . . ?
C15 C3 C4 N1 -177.02(18) . . . . ?
C15 C3 C4 C5 1.5(3) . . . . ?
C16 C5 C6 N2 174.97(16) . . . . ?
C16 C5 C6 C7 -3.2(3) . . . . ?
C17 C7 C8 C9 -178.47(18) . . . . ?
C17 C7 C8 C18 5.1(3) . . . . ?
C18 C8 C9 N2 177.21(18) . . . . ?
C18 C8 C9 C20 -2.1(3) . . . . ?
B1 N1 C1 C2 174.72(17) . . . . ?
B1 N1 C1 C10 -9.0(3) . . . . ?
B1 N1 C4 C3 -175.34(16) . . . . ?
B1 N1 C4 C5 5.9(3) . . . . ?
B1 N2 C6 C5 0.4(3) . . . . ?
B1 N2 C6 C7 179.04(16) . . . . ?
B1 N2 C9 C8 -178.86(16) . . . . ?
B1 N2 C9 C20 0.5(3) . . . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
