# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_ky409_reprocess
_database_code_depnum_ccdc_archive 'CCDC 2084378'
loop_
_audit_author_name
_audit_author_address
'Marina Uzelac'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2021-05-18 deposited with the CCDC.	2022-01-03 downloaded from the CCDC.
;
_audit_creation_date             2021-02-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H13 B Br N'
_chemical_formula_sum            'C20 H13 B Br N'
_chemical_formula_weight         358.03
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H13 B Br N'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   22.9580(7)
_cell_length_b                   9.4271(3)
_cell_length_c                   7.0146(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1518.15(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8543
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      25.2870
_cell_measurement_theta_min      3.7160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.704
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.232
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            31855
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.344
_diffrn_reflns_theta_min         3.404
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  20.00   1.00   17.50    --  -15.66 -16.00 -72.00  107
  2  ω    -52.00  56.00   1.00   17.50    --  -15.66  16.00  97.00  108
  3  ω    -54.00  54.00   1.00   17.50    --   17.38 -16.00 -72.00  108
  4  ω    -19.00  89.00   1.00   17.50    --   17.38  16.00  97.00  108
  5  ω    -83.00   1.00   1.00   17.50    --  -15.66 -57.00  90.00   84
  6  ω    -39.00  11.00   1.00   17.50    --  -15.66 -77.00-120.00   50
  7  ω     -9.00  39.00   1.00   17.50    --   17.38  77.00-120.00   48
  8  ω     -9.00  39.00   1.00   17.50    --   17.38  77.00 -90.00   48
  9  ω     39.00  90.00   1.00   17.50    --   17.38 178.00 120.00   51
 10  ω    -52.00  37.00   1.00   17.50    --   17.38 -37.00  60.00   89
 11  ω     -9.00  39.00   1.00   17.50    --   17.38  77.00  30.00   48
 12  ω     -9.00  39.00   1.00   17.50    --   17.38  77.00 150.00   48
 13  ω    -20.00  56.00   1.00   17.50    --   17.38 -99.00 -90.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0062351000
_diffrn_orient_matrix_UB_12      0.0675046000
_diffrn_orient_matrix_UB_13      0.0396748000
_diffrn_orient_matrix_UB_21      -0.0015177000
_diffrn_orient_matrix_UB_22      -0.0308001000
_diffrn_orient_matrix_UB_23      0.0921593000
_diffrn_orient_matrix_UB_31      0.0302129000
_diffrn_orient_matrix_UB_32      0.0124691000
_diffrn_orient_matrix_UB_33      0.0127897000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.876
_reflns_number_gt                3087
_reflns_number_total             3769
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Flack x determined using 1186 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3769
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0262P)²+0.6498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0679
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C18(H18), C3(H3), C13(H13), C19(H19), C6(H6), C7(H7), C14(H14),
 C5(H5), C16(H16), C17(H17), C8(H8), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br1 Br 0.67855(2) 0.15558(4) 0.68689(9) 0.03039(12) Uani 1 1 d . . . . .
N1 N 0.61424(13) 0.4020(3) 0.8081(5) 0.0214(7) Uani 1 1 d . . . . .
H1 H 0.616236 0.360547 0.917091 0.026 Uiso 1 1 calc R U . . .
C10 C 0.62806(15) 0.5697(4) 0.4788(5) 0.0175(8) Uani 1 1 d . . . . .
C9 C 0.65179(16) 0.6715(4) 0.3465(5) 0.0190(8) Uani 1 1 d . . . . .
C18 C 0.47953(16) 0.8643(4) 0.3953(6) 0.0215(9) Uani 1 1 d . . . . .
H18 H 0.471773 0.901657 0.275247 0.026 Uiso 1 1 calc R U . . .
C3 C 0.69693(14) 0.4740(4) 0.1711(8) 0.0244(8) Uani 1 1 d . . . . .
H3 H 0.715289 0.439283 0.062531 0.029 Uiso 1 1 calc R U . . .
C20 C 0.53862(16) 0.7113(4) 0.5969(5) 0.0191(8) Uani 1 1 d . . . . .
C1 C 0.64974(16) 0.4305(4) 0.4736(6) 0.0203(8) Uani 1 1 d . . . . .
C4 C 0.68366(13) 0.6216(4) 0.1848(10) 0.0228(7) Uani 1 1 d . . . . .
C13 C 0.54559(16) 0.5641(4) 0.9466(6) 0.0218(8) Uani 1 1 d . . . . .
H13 H 0.548108 0.514590 1.060940 0.026 Uiso 1 1 calc R U . . .
C12 C 0.58195(16) 0.5260(4) 0.7917(5) 0.0185(8) Uani 1 1 d . . . . .
C19 C 0.52515(16) 0.7712(4) 0.4179(5) 0.0191(8) Uani 1 1 d . . . . .
H19 H 0.547693 0.747223 0.312580 0.023 Uiso 1 1 calc R U . . .
C6 C 0.70123(18) 0.8629(5) 0.0825(6) 0.0288(10) Uani 1 1 d . . . . .
H6 H 0.715261 0.926478 -0.007810 0.035 Uiso 1 1 calc R U . . .
C7 C 0.67513(16) 0.9131(5) 0.2511(6) 0.0262(10) Uani 1 1 d . . . . .
H7 H 0.674478 1.009845 0.276829 0.031 Uiso 1 1 calc R U . . .
C15 C 0.50076(15) 0.7449(4) 0.7513(6) 0.0199(8) Uani 1 1 d . . . . .
C14 C 0.50705(17) 0.6726(4) 0.9288(6) 0.0228(9) Uani 1 1 d . . . . .
H14 H 0.484644 0.699998 1.032959 0.027 Uiso 1 1 calc R U . . .
C11 C 0.58447(15) 0.6060(4) 0.6247(5) 0.0160(8) Uani 1 1 d . . . . .
C5 C 0.70582(17) 0.7205(5) 0.0524(6) 0.0281(10) Uani 1 1 d . . . . .
H5 H 0.723947 0.687876 -0.057713 0.034 Uiso 1 1 calc R U . . .
C16 C 0.45474(16) 0.8425(4) 0.7247(6) 0.0224(11) Uani 1 1 d . . . . .
H16 H 0.430889 0.865812 0.827167 0.027 Uiso 1 1 calc R U . . .
C17 C 0.44469(16) 0.9034(5) 0.5497(6) 0.0243(9) Uani 1 1 d . . . . .
H17 H 0.415087 0.969781 0.534352 0.029 Uiso 1 1 calc R U . . .
C8 C 0.65064(16) 0.8193(4) 0.3775(6) 0.0209(9) Uani 1 1 d . . . . .
H8 H 0.632765 0.854213 0.486874 0.025 Uiso 1 1 calc R U . . .
C2 C 0.68320(15) 0.3848(4) 0.3134(6) 0.0237(9) Uani 1 1 d . . . . .
H2 H 0.695768 0.291091 0.307459 0.028 Uiso 1 1 calc R U . . .
B1 B 0.64350(18) 0.3426(5) 0.6536(7) 0.0208(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
Br1 B1 1.952(4) . ?
N1 H1 0.8600 . ?
N1 C12 1.389(5) . ?
N1 B1 1.392(5) . ?
C10 C9 1.442(5) . ?
C10 C1 1.404(5) . ?
C10 C11 1.472(5) . ?
C9 C4 1.429(7) . ?
C9 C8 1.410(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.375(5) . ?
C18 C17 1.396(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.428(5) . ?
C3 C2 1.343(6) . ?
C20 C19 1.411(5) . ?
C20 C15 1.424(5) . ?
C20 C11 1.460(5) . ?
C1 C2 1.428(6) . ?
C1 B1 1.517(6) . ?
C4 C5 1.411(7) . ?
C13 H13 0.9300 . ?
C13 C12 1.416(5) . ?
C13 C14 1.358(6) . ?
C12 C11 1.395(5) . ?
C19 H19 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.408(6) . ?
C6 C5 1.362(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.373(5) . ?
C15 C14 1.427(5) . ?
C15 C16 1.413(5) . ?
C14 H14 0.9300 . ?
C5 H5 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.375(6) . ?
C17 H17 0.9300 . ?
C8 H8 0.9300 . ?
C2 H2 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 H1 118.9 . . ?
C12 N1 B1 122.1(4) . . ?
B1 N1 H1 118.9 . . ?
C9 C10 C11 123.3(3) . . ?
C1 C10 C9 118.1(3) . . ?
C1 C10 C11 118.5(3) . . ?
C4 C9 C10 119.0(3) . . ?
C8 C9 C10 123.4(3) . . ?
C8 C9 C4 117.2(4) . . ?
C19 C18 H18 119.5 . . ?
C19 C18 C17 121.0(4) . . ?
C17 C18 H18 119.5 . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.7(5) . . ?
C19 C20 C15 117.0(3) . . ?
C19 C20 C11 123.3(3) . . ?
C15 C20 C11 119.3(3) . . ?
C10 C1 C2 119.6(4) . . ?
C10 C1 B1 117.1(3) . . ?
C2 C1 B1 122.7(4) . . ?
C3 C4 C9 118.9(5) . . ?
C5 C4 C9 119.3(4) . . ?
C5 C4 C3 121.5(5) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C14 C13 C12 120.3(4) . . ?
N1 C12 C13 117.7(4) . . ?
N1 C12 C11 120.1(3) . . ?
C11 C12 C13 122.1(3) . . ?
C18 C19 C20 121.7(4) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.6(4) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.0(4) . . ?
C8 C7 H7 120.0 . . ?
C20 C15 C14 119.7(3) . . ?
C16 C15 C20 120.0(4) . . ?
C16 C15 C14 120.1(3) . . ?
C13 C14 C15 120.4(4) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C20 C11 C10 123.8(3) . . ?
C12 C11 C10 119.1(3) . . ?
C12 C11 C20 116.7(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.4(4) . . ?
C6 C5 H5 119.3 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.0(4) . . ?
C17 C16 H16 119.5 . . ?
C18 C17 H17 120.5 . . ?
C16 C17 C18 119.1(4) . . ?
C16 C17 H17 120.5 . . ?
C9 C8 H8 119.0 . . ?
C7 C8 C9 121.9(4) . . ?
C7 C8 H8 119.0 . . ?
C3 C2 C1 121.5(4) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
N1 B1 Br1 118.0(3) . . ?
N1 B1 C1 118.3(4) . . ?
C1 B1 Br1 123.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_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 C12 C11 C10 -9.2(5) . . . . ?
N1 C12 C11 C20 164.0(3) . . . . ?
C10 C9 C4 C3 -7.3(6) . . . . ?
C10 C9 C4 C5 178.5(3) . . . . ?
C10 C9 C8 C7 178.1(3) . . . . ?
C10 C1 C2 C3 3.3(6) . . . . ?
C10 C1 B1 Br1 -172.5(3) . . . . ?
C10 C1 B1 N1 3.3(5) . . . . ?
C9 C10 C1 C2 -14.8(5) . . . . ?
C9 C10 C1 B1 156.6(3) . . . . ?
C9 C10 C11 C20 34.6(5) . . . . ?
C9 C10 C11 C12 -152.8(3) . . . . ?
C9 C4 C5 C6 4.9(6) . . . . ?
C3 C4 C5 C6 -169.1(4) . . . . ?
C20 C15 C14 C13 -5.5(6) . . . . ?
C20 C15 C16 C17 1.8(6) . . . . ?
C1 C10 C9 C4 16.8(5) . . . . ?
C1 C10 C9 C8 -156.4(3) . . . . ?
C1 C10 C11 C20 -148.5(3) . . . . ?
C1 C10 C11 C12 24.1(5) . . . . ?
C4 C9 C8 C7 4.9(6) . . . . ?
C4 C3 C2 C1 6.6(6) . . . . ?
C13 C12 C11 C10 173.0(3) . . . . ?
C13 C12 C11 C20 -13.9(5) . . . . ?
C12 N1 B1 Br1 -172.0(3) . . . . ?
C12 N1 B1 C1 12.0(5) . . . . ?
C12 C13 C14 C15 3.1(6) . . . . ?
C19 C18 C17 C16 -3.1(6) . . . . ?
C19 C20 C15 C14 171.3(4) . . . . ?
C19 C20 C15 C16 -4.5(5) . . . . ?
C19 C20 C11 C10 11.3(6) . . . . ?
C19 C20 C11 C12 -161.5(3) . . . . ?
C6 C7 C8 C9 1.5(6) . . . . ?
C7 C6 C5 C4 1.6(6) . . . . ?
C15 C20 C19 C18 3.6(5) . . . . ?
C15 C20 C11 C10 -176.2(3) . . . . ?
C15 C20 C11 C12 11.1(5) . . . . ?
C15 C16 C17 C18 2.1(6) . . . . ?
C14 C13 C12 N1 -170.8(4) . . . . ?
C14 C13 C12 C11 7.1(6) . . . . ?
C14 C15 C16 C17 -174.0(4) . . . . ?
C11 C10 C9 C4 -166.3(4) . . . . ?
C11 C10 C9 C8 20.6(5) . . . . ?
C11 C10 C1 C2 168.1(3) . . . . ?
C11 C10 C1 B1 -20.5(5) . . . . ?
C11 C20 C19 C18 176.3(4) . . . . ?
C11 C20 C15 C14 -1.7(5) . . . . ?
C11 C20 C15 C16 -177.5(3) . . . . ?
C5 C6 C7 C8 -4.8(6) . . . . ?
C16 C15 C14 C13 170.3(4) . . . . ?
C17 C18 C19 C20 0.2(6) . . . . ?
C8 C9 C4 C3 166.2(3) . . . . ?
C8 C9 C4 C5 -7.9(6) . . . . ?
C2 C3 C4 C9 -4.4(6) . . . . ?
C2 C3 C4 C5 169.6(4) . . . . ?
C2 C1 B1 Br1 -1.4(5) . . . . ?
C2 C1 B1 N1 174.4(3) . . . . ?
B1 N1 C12 C13 169.0(3) . . . . ?
B1 N1 C12 C11 -9.0(5) . . . . ?
B1 C1 C2 C3 -167.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.317
_oxdiff_exptl_absorpt_empirical_full_min 0.852
####################################################################### 
# 
# 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_mi21007c
_database_code_depnum_ccdc_archive 'CCDC 2084380'
loop_
_audit_author_name
_audit_author_address
'Marina Uzelac'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2021-05-18 deposited with the CCDC.	2022-01-03 downloaded from the CCDC.
;
_audit_creation_date             2021-05-10
_audit_creation_method           
;
Olex2 1.3-beta
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
g.s.nichol@ed.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1(C33 H26 B1 N1)'
_chemical_formula_sum            'C33 H26 B N'
_chemical_formula_weight         447.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         C33H26BN
_chemical_oxdiff_usercomment     '@ 120 K KY461'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6409(2)
_cell_length_b                   12.0504(4)
_cell_length_c                   15.9138(6)
_cell_angle_alpha                78.061(3)
_cell_angle_beta                 78.902(3)
_cell_angle_gamma                79.901(3)
_cell_volume                     1210.41(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8254
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      76.2060
_cell_measurement_theta_min      3.7780
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.829
_exptl_absorpt_coefficient_mu    0.528
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 5 2 0.1368
4 4 5 0.1456
3 -4 -1 0.1655
1 -7 -4 0.1637
-4 -4 -5 0.0919
0 0 -1 0.0165
0 0 1 0.0165

_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of hexane and dichloromethane  by slow evaporation'
_exptl_crystal_size_max          0.368
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.033
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.5900 5.2296 1.6795 0.1097 0.3135 0.9432
3.8773 4.1187 4.7127 0.2839 0.8019 -0.5257
3.1868 -4.1223 -0.6678 -0.0483 -0.1397 -0.9890
0.5575 -7.2000 -4.0358 -0.2515 -0.7138 -0.6537
-3.8758 -4.1237 -4.7150 -0.2840 -0.8023 0.5250
0.0000 -0.0000 -0.9996 -0.1000 0.0040 -0.0051
-0.0000 0.0000 0.9996 0.1000 -0.0040 0.0051

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19449
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.684
_diffrn_reflns_theta_min         3.787
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00 -14.00   1.00    1.00    --    0.00 142.00  26.00   59
  2  ω    -64.00  -8.00   1.00    1.00    --    0.00 128.00-145.00   56
  3  ω   -143.00 -74.00   1.00    3.00    --  -59.00-128.00 140.00   69
  4  ω   -100.00 -14.00   1.00    3.00    --  -59.00 142.00  26.00   86
  5  ω   -144.00 -66.00   1.00    3.00    --  -59.00-142.00 -30.00   78
  6  ω     36.00 125.00   1.00    3.00    --   59.00-142.00 -30.00   89
  7  ω     30.00 114.00   1.00    3.00    --   59.00-128.00 140.00   84
  8  ω     96.00 143.00   1.00    3.00    --   59.00 128.00-145.00   47
  9  ω     88.00 143.00   1.00    3.00    --   59.00 142.00  26.00   55
 10  ω     36.00 125.00   1.00    3.00    --  118.00-142.00 -30.00   89
 11  ω     96.00 178.00   1.00    3.00    --  118.00 128.00-145.00   82
 12  ω     87.00 172.00   1.00    3.00    --  118.00 142.00  26.00   85
 13  ω     34.00 114.00   1.00    3.00    --  118.00-128.00 140.00   80
 14  ω    -96.00 -39.00   1.00    1.00    --    0.00-178.00  90.00   57
 15  ω    -95.00 -37.00   1.00    1.00    --    0.00 178.00 -90.00   58
 16  ω    -39.00  42.00   1.00    1.00    --    0.00  77.00   0.00   81
 17  ω   -151.00 -82.00   1.00    3.00    --  -59.00 -77.00-120.00   69
 18  ω   -143.00 -22.00   1.00    3.00    --  -59.00 -38.00 -60.00  121
 19  ω   -151.00 -82.00   1.00    3.00    --  -59.00 -77.00   0.00   69
 20  ω    103.00 151.00   1.00    3.00    --   59.00  77.00   0.00   48
 21  ω     97.00 143.00   1.00    3.00    --   59.00 125.00 -60.00   46
 22  ω     97.00 143.00   1.00    3.00    --   59.00 125.00-180.00   46
 23  ω     97.00 143.00   1.00    3.00    --   59.00 125.00 120.00   46
 24  ω    103.00 151.00   1.00    3.00    --   59.00  77.00 -30.00   48
 25  ω     32.00 109.00   1.00    3.00    --  118.00-111.00 150.00   77
 26  ω     82.00 178.00   1.00    3.00    --  118.00  45.00 -90.00   96
 27  ω     81.00 178.00   1.00    3.00    --  118.00  61.00-150.00   97
 28  ω     32.00 109.00   1.00    3.00    --  118.00-111.00  90.00   77
 29  ω     27.00 106.00   1.00    3.00    --  118.00 -94.00  30.00   79
 30  ω     26.00 157.00   1.00    3.00    --  118.00 -77.00-120.00  131
 31  ω    104.00 178.00   1.00    3.00    --  118.00 111.00 -90.00   74
 32  ω     27.00 106.00   1.00    3.00    --  118.00 -94.00 -60.00   79
 33  ω     28.00 178.00   1.00    3.00    --  118.00  15.00 -90.00  150
 34  ω     82.00 178.00   1.00    3.00    --  118.00  50.00-177.08   96
 35  ω     34.00 154.00   1.00    3.00    --  118.00 -45.00   0.00  120
 36  ω    104.00 178.00   1.00    3.00    --  118.00 111.00  90.00   74
 37  ω    103.00 178.00   1.00    3.00    --  118.00  77.00 -30.00   75
 38  ω     27.00 106.00   1.00    3.00    --  118.00 -94.00-150.00   79
 39  ω     33.00 155.00   1.00    3.00    --  118.00 -61.00 -30.00  122
 40  ω     27.00 106.00   1.00    3.00    --  118.00 -94.00 150.00   79
 41  ω     27.00 106.00   1.00    3.00    --  118.00 -94.00 120.00   79
 42  ω     82.00 178.00   1.00    3.00    --  118.00  45.00  30.00   96
 43  ω     27.00 106.00   1.00    3.00    --  118.00 -94.00-120.00   79
 44  ω     32.00 109.00   1.00    3.00    --  118.00-111.00 120.00   77
 45  ω    104.00 178.00   1.00    3.00    --  118.00 111.00 -30.00   74
 46  ω     61.00 146.00   1.00    3.00    --  118.00 178.00  30.00   85
 47  ω     57.00  83.00   1.00    3.00    --  118.00 -94.00-180.00   26
 48  ω    105.00 152.00   1.00    3.00    --  118.00  30.00  60.00   47
 49  ω     72.00 103.00   1.00    3.00    --  118.00-111.00  30.00   31
 50  ω    153.00 178.00   1.00    3.00    --  118.00  77.00  60.00   25
 51  ω     61.00 109.00   1.00    3.00    --  118.00-111.00-150.00   48
 52  ω     74.00 116.00   1.00    3.00    --  118.00 -61.00-120.00   42
 53  ω     37.00  62.00   1.00    3.00    --  118.00-111.00  30.00   25
 54  ω    104.00 134.00   1.00    3.00    --  118.00  77.00  60.00   30
 55  ω    106.00 135.00   1.00    3.00    --  118.00  77.00  90.00   29
 56  ω     87.00 128.00   1.00    3.00    --  118.00 -77.00  60.00   41
 57  ω    124.00 150.00   1.00    3.00    --  118.00 111.00 150.00   26
 58  ω     66.00 108.00   1.00    3.00    --  118.00 178.00 120.00   42
 59  ω     68.00 105.00   1.00    3.00    --  118.00-111.00 -60.00   37
 60  ω    111.00 147.00   1.00    3.00    --  118.00  45.00 -30.00   36
 61  ω     91.00 117.00   1.00    3.00    --  118.00 -61.00 150.00   26
 62  ω     97.00 123.00   1.00    3.00    --  118.00 -83.00 -64.23   26
 63  ω     81.00 134.00   1.00    3.00    --  118.00  61.00 -30.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction SuperNova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0239555000
_diffrn_orient_matrix_UB_12      -0.0230180000
_diffrn_orient_matrix_UB_13      0.1000672000
_diffrn_orient_matrix_UB_21      0.0960733000
_diffrn_orient_matrix_UB_22      0.1087885000
_diffrn_orient_matrix_UB_23      -0.0039554000
_diffrn_orient_matrix_UB_31      -0.2172990000
_diffrn_orient_matrix_UB_32      0.0711121000
_diffrn_orient_matrix_UB_33      0.0050904000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7191
_reflns_number_total             9193
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0081(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     592
_refine_ls_number_reflns         9193
_refine_ls_number_restraints     64
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0571
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1151P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1596
_refine_ls_wR_factor_ref         0.1660
_refine_special_details          
;
All of the crystals tested in this sample suffered from quite severe twinning.  A detector distance of 65 mm was used.  CrysAlisPro was used to apply twin law [-1 0 0 / 0 -1 0 / -0.7746 -0.4716 1] during integration, with refined twin scale fraction 0.2477(13).  The structure suffers from whole molecule disorder, with the exception of N1/C1, C4/C17 & C7/C20, three pairs of atoms which were constrained to have identical coordinates and displacement ellipsoid parameters.  Some geometric similarity restraints were used.  The N-bound H atoms were identified from difference maps and refined using a riding model.


#===============================================================================
#>>> The Following Improvement and Query ALERTS were generated - (Acta-Mode) <<<
#===============================================================================
     Format: alert-number_ALERT_alert-type_alert-level text

088_ALERT_3_C Poor Data / Parameter Ratio ....................       8.55 Note
420_ALERT_2_C D-H Bond Without Acceptor  N1       --H1       .     Please Check
788_ALERT_4_C Change  B1       into  B        in MoietyFormula     Please Do

Consequence of whole molecule disorder

906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.937 Check
918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          1 Check

No action taken


#===============================================================================
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7527(12)
 0.2473(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Shared sites
{N1, C1A}
{C1, N1A}
{C4, C17A}
{C17, C4A}
{C7, C20A}
{C20, C7A}
4. Restrained distances
 N1A-H1AA
 0.83 with sigma of 0.02
 N1-H1
 0.84 with sigma of 0.02
 C26-C31 \\sim C26A-C31A
 with sigma of 0.02
 C29-C30 \\sim C29A-C30A
 with sigma of 0.02
 C25-C26 \\sim C25A-C26A
 with sigma of 0.02
 C25-C30 \\sim C25A-C30A
 with sigma of 0.02
 C26-C27 \\sim C26A-C27A
 with sigma of 0.02
 C25-B1 \\sim C25A-B1
 with sigma of 0.02
 C25-B1A \\sim C25A-B1A
 with sigma of 0.02
 C30-B1A \\sim C30A-B1A
 with sigma of 0.04
 C27-C29 \\sim C27A-C29A
 with sigma of 0.04
 C27-C32 \\sim C27A-C32A
 with sigma of 0.04
 C28-C29 \\sim C28A-C29A
 with sigma of 0.02
 C28-C30 \\sim C28A-C30A
 with sigma of 0.04
 C29-C32 \\sim C29A-C32A
 with sigma of 0.04
 C27-C28 \\sim C27A-C28A
 with sigma of 0.02
 C27-C31 \\sim C27A-C31A
 with sigma of 0.04
 C28-C32 \\sim C28A-C32A
 with sigma of 0.02
 C29-C33 \\sim C29A-C33A
 with sigma of 0.04
 C30-B1 \\sim C30A-B1
 with sigma of 0.04
 C25-C27 \\sim C25A-C27A
 with sigma of 0.04
 C25-C29 \\sim C25A-C29A
 with sigma of 0.04
 C25-C31 \\sim C25A-C31A
 with sigma of 0.04
 C25-C33 \\sim C25A-C33A
 with sigma of 0.04
 C30-C33 \\sim C30A-C33A
 with sigma of 0.02
 C26-C28 \\sim C26A-C28A
 with sigma of 0.04
 C26-C30 \\sim C26A-C30A
 with sigma of 0.04
 C26-B1 \\sim C26A-B1
 with sigma of 0.04
 C26-B1A \\sim C26A-B1A
 with sigma of 0.04
5. Restrained planarity
 C26, C27, C28, C29, C30
 with sigma of 0.1
 C25, C26, C27, C28, C29, C30
 with sigma of 0.1
6. Uiso/Uaniso restraints and constraints
Uanis(N1) = Uanis(C1A)
Uanis(C1) = Uanis(N1A)
Uanis(C4) = Uanis(C17A)
Uanis(C17) = Uanis(C4A)
Uanis(C7) = Uanis(C20A)
Uanis(C20) = Uanis(C7A)
7. Rigid body (RIGU) restrains
 C25, C26, C27, C28, C29, C30
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C26, C27, C28, C29, C30
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
8. Others
 Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=
 Sof(H5A)=Sof(C6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=
 Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(C12A)=Sof(C13A)=Sof(C15A)=Sof(C16A)=
 Sof(H16A)=Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=
 Sof(H20A)=Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(C24A)=Sof(C40)=
 Sof(N1A)=Sof(H1AA)=Sof(B1A)=Sof(C25A)=Sof(C26A)=Sof(C27A)=Sof(H27A)=Sof(C28A)=
 Sof(C29A)=Sof(H29A)=Sof(C30A)=Sof(C31A)=Sof(H31A)=Sof(H31B)=Sof(H31C)=
 Sof(C32A)=Sof(H32A)=Sof(H32B)=Sof(H32C)=Sof(C33A)=Sof(H33A)=Sof(H33B)=
 Sof(H33C)=1-FVAR(1)
 Sof(N1)=Sof(H1)=Sof(C1)=Sof(H1B)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(C4)=Sof(H4)=
 Sof(C5)=Sof(H5)=Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=
 Sof(C10)=Sof(H10)=Sof(C11)=Sof(C12)=Sof(C13)=Sof(C14)=Sof(C15)=Sof(C16)=
 Sof(H16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=
 Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(C24)=Sof(C25)=Sof(C26)=
 Sof(C27)=Sof(H27)=Sof(C28)=Sof(C29)=Sof(H29)=Sof(C30)=Sof(C31)=Sof(H31D)=
 Sof(H31E)=Sof(H31F)=Sof(C32)=Sof(H32D)=Sof(H32E)=Sof(H32F)=Sof(C33)=Sof(H33D)=
 Sof(H33E)=Sof(H33F)=Sof(B1)=FVAR(1)
9.a Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C1(H1B), C2(H2), C2A(H2A), C4(H4), C4A(H4A), C5(H5), C5A(H5A),
 C7(H7), C7A(H7A), C8(H8), C8A(H8A), C9(H9), C9A(H9A), C10(H10), C10A(H10A),
 C16(H16), C16A(H16A), C17(H17), C17A(H17A), C19(H19), C19A(H19A), C20(H20),
 C20A(H20A), C21(H21), C21A(H21A), C22(H22), C22A(H22A), C27(H27), C29(H29),
 C27A(H27A), C29A(H29A)
9.b Idealised Me refined as rotating group:
 C31(H31D,H31E,H31F), C32(H32D,H32E,H32F), C33(H33D,H33E,H33F), C31A(H31A,H31B,
 H31C), C32A(H32A,H32B,H32C), C33A(H33A,H33B,H33C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
C1A C 0.9508(2) 0.82928(12) 0.52408(9) 0.0361(3) Uani 0.483(2) 1 d . . P A 2
H1A H 0.992835 0.849461 0.463029 0.043 Uiso 0.483(2) 1 calc R U P A 2
N1 N 0.9508(2) 0.82928(12) 0.52408(9) 0.0361(3) Uani 0.517(2) 1 d D . P A 1
H1 H 1.050(5) 0.861(3) 0.490(2) 0.043 Uiso 0.517(2) 1 d D U P A 1
C1 C 0.5294(2) 0.65730(13) 0.52563(10) 0.0393(4) Uani 0.517(2) 1 d . . P A 1
H1B H 0.531099 0.666305 0.464774 0.047 Uiso 0.517(2) 1 calc R U P A 1
C2 C 0.3870(5) 0.5808(3) 0.5927(3) 0.0386(8) Uani 0.517(2) 1 d . . P A 1
H2 H 0.278649 0.552870 0.575687 0.046 Uiso 0.517(2) 1 calc R U P A 1
C2A C 1.0514(5) 0.8749(2) 0.5820(2) 0.0317(7) Uani 0.483(2) 1 d . . P A 2
H2A H 1.173261 0.910124 0.561719 0.038 Uiso 0.483(2) 1 calc R U P A 2
C3 C 0.4214(5) 0.5537(2) 0.6790(2) 0.0371(7) Uani 0.517(2) 1 d . . P A 1
C3A C 0.9534(6) 0.8624(3) 0.6697(2) 0.0309(7) Uani 0.483(2) 1 d . . P A 2
C4 C 0.3196(3) 0.47446(17) 0.72824(17) 0.0569(5) Uani 0.517(2) 1 d . . P A 1
H4 H 0.225013 0.442677 0.705469 0.068 Uiso 0.517(2) 1 calc R U P A 1
C4A C 1.0095(3) 0.92045(16) 0.72404(14) 0.0488(4) Uani 0.483(2) 1 d . . P A 2
H4A H 1.118466 0.965254 0.700968 0.059 Uiso 0.483(2) 1 calc R U P A 2
C5 C 0.3516(8) 0.4338(3) 0.8200(3) 0.0578(11) Uani 0.517(2) 1 d . . P A 1
H5 H 0.259975 0.388067 0.859955 0.069 Uiso 0.517(2) 1 calc R U P A 1
C5A C 0.9222(6) 0.9198(3) 0.8093(3) 0.0489(9) Uani 0.483(2) 1 d . . P A 2
H5A H 0.986056 0.947021 0.848073 0.059 Uiso 0.483(2) 1 calc R U P A 2
C6 C 0.5252(7) 0.4657(3) 0.8467(2) 0.0465(9) Uani 0.517(2) 1 d . . P A 1
C6A C 0.7283(6) 0.8754(3) 0.8366(3) 0.0366(8) Uani 0.483(2) 1 d . . P A 2
C7 C 0.5846(3) 0.41527(15) 0.92041(13) 0.0537(5) Uani 0.517(2) 1 d . . P A 1
H7 H 0.502943 0.361709 0.957651 0.064 Uiso 0.517(2) 1 calc R U P A 1
C7A C 0.5962(3) 0.89369(15) 0.91760(12) 0.0483(5) Uani 0.483(2) 1 d . . P A 2
H7A H 0.646616 0.930824 0.954852 0.058 Uiso 0.483(2) 1 calc R U P A 2
C8 C 0.7637(7) 0.4352(3) 0.9488(2) 0.0587(11) Uani 0.517(2) 1 d . . P A 1
H8 H 0.798366 0.399649 1.004235 0.070 Uiso 0.517(2) 1 calc R U P A 1
C8A C 0.4121(6) 0.8625(3) 0.9429(2) 0.0429(8) Uani 0.483(2) 1 d . . P A 2
H8A H 0.336675 0.871000 0.998839 0.051 Uiso 0.483(2) 1 calc R U P A 2
C9 C 0.8864(7) 0.5105(3) 0.8900(2) 0.0483(9) Uani 0.517(2) 1 d . . P A 1
H9 H 1.011147 0.524108 0.904433 0.058 Uiso 0.517(2) 1 calc R U P A 1
C9A C 0.3282(6) 0.8162(3) 0.8856(2) 0.0352(7) Uani 0.483(2) 1 d . . P A 2
H9A H 0.190663 0.798256 0.901200 0.042 Uiso 0.483(2) 1 calc R U P A 2
C10 C 0.8276(8) 0.5646(6) 0.8117(5) 0.0394(12) Uani 0.517(2) 1 d . . P A 1
H10 H 0.913986 0.613983 0.772346 0.047 Uiso 0.517(2) 1 calc R U P A 1
C10A C 0.4437(11) 0.7966(9) 0.8066(7) 0.0292(13) Uani 0.483(2) 1 d . . P A 2
H10A H 0.384022 0.766245 0.768069 0.035 Uiso 0.483(2) 1 calc R U P A 2
C11 C 0.6414(9) 0.5482(4) 0.7886(4) 0.0330(10) Uani 0.517(2) 1 d . . P A 1
C11A C 0.6524(15) 0.8214(8) 0.7822(5) 0.0282(14) Uani 0.483(2) 1 d . . P A 2
C12 C 0.5726(6) 0.6021(5) 0.7066(5) 0.0283(8) Uani 0.517(2) 1 d . . P A 1
C12A C 0.7759(8) 0.8029(4) 0.6988(4) 0.0223(8) Uani 0.483(2) 1 d . . P A 2
C13 C 0.6594(8) 0.6958(6) 0.6464(3) 0.0241(6) Uani 0.517(2) 1 d . . P A 1
C13A C 0.7326(7) 0.7377(5) 0.6411(3) 0.0217(6) Uani 0.483(2) 1 d . . P A 2
C14 C 0.6464(4) 0.7085(2) 0.55729(19) 0.0271(6) Uani 0.517(2) 1 d . . P A 1
C15 C 0.9091(4) 0.8336(2) 0.61209(18) 0.0274(6) Uani 0.517(2) 1 d . . P A 1
C15A C 0.5019(4) 0.6168(2) 0.6089(2) 0.0276(6) Uani 0.483(2) 1 d . . P A 2
C16 C 1.0335(6) 0.9009(3) 0.6383(3) 0.0362(7) Uani 0.517(2) 1 d . . P A 1
H16 H 1.137880 0.934267 0.595919 0.043 Uiso 0.517(2) 1 calc R U P A 1
C16A C 0.3566(6) 0.5380(3) 0.6354(3) 0.0352(8) Uani 0.483(2) 1 d . . P A 2
H16A H 0.281098 0.524947 0.594226 0.042 Uiso 0.483(2) 1 calc R U P A 2
C17 C 1.0095(3) 0.92045(16) 0.72404(14) 0.0488(4) Uani 0.517(2) 1 d . . P A 1
H17 H 1.107872 0.953279 0.743763 0.059 Uiso 0.517(2) 1 calc R U P A 1
C17A C 0.3196(3) 0.47446(17) 0.72824(17) 0.0569(5) Uani 0.483(2) 1 d . . P A 2
H17A H 0.210240 0.429767 0.750444 0.068 Uiso 0.483(2) 1 calc R U P A 2
C18 C 0.8208(5) 0.8861(2) 0.7804(2) 0.0365(7) Uani 0.517(2) 1 d . . P A 1
C18A C 0.4590(5) 0.4877(3) 0.7769(2) 0.0349(7) Uani 0.483(2) 1 d . . P A 2
C19 C 0.7628(6) 0.9208(4) 0.8623(3) 0.0499(9) Uani 0.517(2) 1 d . . P A 1
H19 H 0.848205 0.965825 0.878381 0.060 Uiso 0.517(2) 1 calc R U P A 1
C19A C 0.4503(7) 0.4146(3) 0.8599(3) 0.0421(9) Uani 0.483(2) 1 d . . P A 2
H19A H 0.350855 0.362969 0.875870 0.050 Uiso 0.483(2) 1 calc R U P A 2
C20 C 0.5962(3) 0.89369(15) 0.91760(12) 0.0483(5) Uani 0.517(2) 1 d . . P A 1
H20 H 0.568703 0.913108 0.974004 0.058 Uiso 0.517(2) 1 calc R U P A 1
C20A C 0.5846(3) 0.41527(15) 0.92041(13) 0.0537(5) Uani 0.483(2) 1 d . . P A 2
H20A H 0.573761 0.369372 0.976893 0.064 Uiso 0.483(2) 1 calc R U P A 2
C21 C 0.4541(6) 0.8329(3) 0.8901(2) 0.0389(7) Uani 0.517(2) 1 d . . P A 1
H21 H 0.325438 0.819795 0.925939 0.047 Uiso 0.517(2) 1 calc R U P A 1
C21A C 0.7350(6) 0.4907(3) 0.8882(2) 0.0395(8) Uani 0.483(2) 1 d . . P A 2
H21A H 0.834982 0.490304 0.923764 0.047 Uiso 0.483(2) 1 calc R U P A 2
C22 C 0.5093(9) 0.7949(8) 0.8115(6) 0.0288(13) Uani 0.517(2) 1 d . . P A 1
H22 H 0.419307 0.753044 0.794971 0.035 Uiso 0.517(2) 1 calc R U P A 1
C22A C 0.7467(10) 0.5645(5) 0.8093(4) 0.0289(11) Uani 0.483(2) 1 d . . P A 2
H22A H 0.851081 0.613243 0.792536 0.035 Uiso 0.483(2) 1 calc R U P A 2
C23 C 0.6966(12) 0.8165(6) 0.7549(4) 0.0265(15) Uani 0.517(2) 1 d . . P A 1
C23A C 0.6024(7) 0.5679(4) 0.7526(5) 0.0245(9) Uani 0.483(2) 1 d . . P A 2
C24 C 0.7607(6) 0.7784(4) 0.6720(4) 0.0232(9) Uani 0.517(2) 1 d . . P A 1
C24A C 0.6075(7) 0.6436(6) 0.6691(4) 0.0231(7) Uani 0.483(2) 1 d . . P A 2
C25 C 0.8193(6) 0.7885(3) 0.3870(3) 0.0279(8) Uani 0.517(2) 1 d D . P A 1
C26 C 0.6649(11) 0.8569(6) 0.3431(5) 0.0305(13) Uani 0.517(2) 1 d D . P A 1
C27 C 0.690(2) 0.8705(14) 0.2534(7) 0.036(2) Uani 0.517(2) 1 d D . P A 1
H27 H 0.584579 0.917475 0.224615 0.043 Uiso 0.517(2) 1 calc R U P A 1
C28 C 0.8614(16) 0.8196(8) 0.2034(4) 0.034(3) Uani 0.517(2) 1 d D . P A 1
C29 C 1.0153(16) 0.7446(8) 0.2464(5) 0.027(2) Uani 0.517(2) 1 d D . P A 1
H29 H 1.128835 0.702674 0.214788 0.033 Uiso 0.517(2) 1 calc R U P A 1
C30 C 0.9942(11) 0.7345(6) 0.3370(5) 0.0270(13) Uani 0.517(2) 1 d D . P A 1
C31 C 0.4750(9) 0.9215(5) 0.3909(5) 0.0419(12) Uani 0.517(2) 1 d D . P A 1
H31D H 0.424966 0.872633 0.445660 0.063 Uiso 0.517(2) 1 calc R U P A 1
H31E H 0.365939 0.942483 0.354584 0.063 Uiso 0.517(2) 1 calc R U P A 1
H31F H 0.511706 0.991026 0.403465 0.063 Uiso 0.517(2) 1 calc R U P A 1
C32 C 0.888(2) 0.8354(16) 0.1044(8) 0.052(2) Uani 0.517(2) 1 d D . P A 1
H32D H 0.755638 0.832325 0.087051 0.078 Uiso 0.517(2) 1 calc R U P A 1
H32E H 0.992275 0.774224 0.084040 0.078 Uiso 0.517(2) 1 calc R U P A 1
H32F H 0.933646 0.909869 0.078400 0.078 Uiso 0.517(2) 1 calc R U P A 1
C33 C 1.1578(13) 0.6509(8) 0.3826(8) 0.0473(19) Uani 0.517(2) 1 d D . P A 1
H33D H 1.126033 0.651276 0.445325 0.071 Uiso 0.517(2) 1 calc R U P A 1
H33E H 1.294850 0.674198 0.359515 0.071 Uiso 0.517(2) 1 calc R U P A 1
H33F H 1.157429 0.573513 0.372294 0.071 Uiso 0.517(2) 1 calc R U P A 1
C40 C 0.8115(4) 0.7646(2) 0.5510(2) 0.0236(6) Uani 0.483(2) 1 d . . P A 2
N1A N 0.5294(2) 0.65730(13) 0.52563(10) 0.0393(4) Uani 0.483(2) 1 d D . P A 2
H1AA H 0.471(6) 0.642(4) 0.488(2) 0.047 Uiso 0.483(2) 1 d D U P A 2
B1 B 0.7995(5) 0.7766(3) 0.4893(2) 0.0280(7) Uani 0.517(2) 1 d . . P A 1
B1A B 0.7095(5) 0.7273(3) 0.4842(2) 0.0255(7) Uani 0.483(2) 1 d . . P A 2
C25A C 0.7689(7) 0.7604(4) 0.3821(3) 0.0270(8) Uani 0.483(2) 1 d D . P A 2
C26A C 0.6358(12) 0.8383(6) 0.3305(6) 0.0311(14) Uani 0.483(2) 1 d D . P A 2
C27A C 0.687(2) 0.8633(15) 0.2409(8) 0.033(2) Uani 0.483(2) 1 d D . P A 2
H27A H 0.591924 0.913090 0.207509 0.039 Uiso 0.483(2) 1 calc R U P A 2
C28A C 0.878(2) 0.8153(10) 0.1990(6) 0.045(3) Uani 0.483(2) 1 d D . P A 2
C29A C 1.011(2) 0.7466(12) 0.2523(7) 0.048(4) Uani 0.483(2) 1 d D . P A 2
H29A H 1.148513 0.722742 0.225977 0.058 Uiso 0.483(2) 1 calc R U P A 2
C30A C 0.9584(12) 0.7106(6) 0.3403(6) 0.0276(14) Uani 0.483(2) 1 d D . P A 2
C31A C 0.4344(10) 0.8978(6) 0.3737(5) 0.0448(14) Uani 0.483(2) 1 d D . P A 2
H31A H 0.402015 0.858789 0.434139 0.067 Uiso 0.483(2) 1 calc R U P A 2
H31B H 0.322561 0.895516 0.342227 0.067 Uiso 0.483(2) 1 calc R U P A 2
H31C H 0.448245 0.977728 0.372819 0.067 Uiso 0.483(2) 1 calc R U P A 2
C32A C 0.936(3) 0.8451(18) 0.1024(8) 0.055(3) Uani 0.483(2) 1 d D . P A 2
H32A H 0.883737 0.792724 0.074887 0.083 Uiso 0.483(2) 1 calc R U P A 2
H32B H 1.087334 0.837989 0.086768 0.083 Uiso 0.483(2) 1 calc R U P A 2
H32C H 0.875127 0.923984 0.082234 0.083 Uiso 0.483(2) 1 calc R U P A 2
C33A C 1.1089(14) 0.6258(8) 0.3889(8) 0.0422(17) Uani 0.483(2) 1 d D . P A 2
H33A H 1.099989 0.643722 0.446893 0.063 Uiso 0.483(2) 1 calc R U P A 2
H33B H 1.249906 0.629872 0.356917 0.063 Uiso 0.483(2) 1 calc R U P A 2
H33C H 1.075023 0.548349 0.394471 0.063 Uiso 0.483(2) 1 calc R U P A 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
C1A H1A 0.9500 . ?
C1A C2A 1.474(4) . ?
C1A C40 1.268(3) . ?
N1 H1 0.86(2) . ?
N1 C15 1.384(3) . ?
N1 B1 1.517(4) . ?
C1 H1B 0.9500 . ?
C1 C2 1.548(5) . ?
C1 C14 1.298(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(6) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.412(5) . ?
C3 C4 1.302(4) . ?
C3 C12 1.422(6) . ?
C3A C4A 1.357(4) . ?
C3A C12A 1.437(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.484(6) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.367(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.438(6) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.436(5) . ?
C6 C7 1.304(4) . ?
C6 C11 1.432(7) . ?
C6A C7A 1.447(4) . ?
C6A C11A 1.394(12) . ?
C7 H7 0.9500 . ?
C7 C8 1.424(5) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.306(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.406(6) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.402(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.375(8) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.384(11) . ?
C10 H10 0.9500 . ?
C10 C11 1.412(7) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.432(12) . ?
C11 C12 1.453(7) . ?
C11A C12A 1.456(6) . ?
C12 C13 1.447(7) . ?
C12A C13A 1.423(6) . ?
C13 C14 1.413(4) . ?
C13 C24 1.454(6) . ?
C13A C24A 1.468(7) . ?
C13A C40 1.418(5) . ?
C14 B1 1.543(4) . ?
C15 C16 1.423(4) . ?
C15 C24 1.389(5) . ?
C15A C16A 1.418(5) . ?
C15A C24A 1.408(5) . ?
C15A N1A 1.303(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.406(4) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.512(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.464(4) . ?
C17A H17A 0.9500 . ?
C17A C18A 1.364(4) . ?
C18 C19 1.413(5) . ?
C18 C23 1.436(9) . ?
C18A C19A 1.424(5) . ?
C18A C23A 1.420(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.318(5) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.435(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.467(4) . ?
C20A H20A 0.9500 . ?
C20A C21A 1.420(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.382(9) . ?
C21A H21A 0.9500 . ?
C21A C22A 1.379(7) . ?
C22 H22 0.9500 . ?
C22 C23 1.418(10) . ?
C22A H22A 0.9500 . ?
C22A C23A 1.428(7) . ?
C23 C24 1.449(7) . ?
C23A C24A 1.446(7) . ?
C25 C26 1.400(8) . ?
C25 C30 1.413(8) . ?
C25 B1 1.586(6) . ?
C26 C27 1.383(11) . ?
C26 C31 1.519(9) . ?
C27 H27 0.9500 . ?
C27 C28 1.381(12) . ?
C28 C29 1.421(10) . ?
C28 C32 1.528(11) . ?
C29 H29 0.9500 . ?
C29 C30 1.404(10) . ?
C30 C33 1.530(10) . ?
C31 H31D 0.9800 . ?
C31 H31E 0.9800 . ?
C31 H31F 0.9800 . ?
C32 H32D 0.9800 . ?
C32 H32E 0.9800 . ?
C32 H32F 0.9800 . ?
C33 H33D 0.9800 . ?
C33 H33E 0.9800 . ?
C33 H33F 0.9800 . ?
C40 B1A 1.542(4) . ?
N1A H1AA 0.84(2) . ?
N1A B1A 1.548(4) . ?
B1A C25A 1.578(6) . ?
C25A C26A 1.416(9) . ?
C25A C30A 1.402(9) . ?
C26A C27A 1.383(11) . ?
C26A C31A 1.513(9) . ?
C27A H27A 0.9500 . ?
C27A C28A 1.404(12) . ?
C28A C29A 1.386(12) . ?
C28A C32A 1.494(13) . ?
C29A H29A 0.9500 . ?
C29A C30A 1.373(12) . ?
C30A C33A 1.501(11) . ?
C31A H31A 0.9800 . ?
C31A H31B 0.9800 . ?
C31A H31C 0.9800 . ?
C32A H32A 0.9800 . ?
C32A H32B 0.9800 . ?
C32A H32C 0.9800 . ?
C33A H33A 0.9800 . ?
C33A H33B 0.9800 . ?
C33A H33C 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
C2A C1A H1A 118.1 . . ?
C40 C1A H1A 118.1 . . ?
C40 C1A C2A 123.8(2) . . ?
C15 N1 H1 121(3) . . ?
C15 N1 B1 116.5(2) . . ?
B1 N1 H1 122(3) . . ?
C2 C1 H1B 121.9 . . ?
C14 C1 H1B 121.9 . . ?
C14 C1 C2 116.1(2) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 H2 120.8 . . ?
C1A C2A H2A 122.4 . . ?
C3A C2A C1A 115.1(2) . . ?
C3A C2A H2A 122.4 . . ?
C2 C3 C12 121.1(4) . . ?
C4 C3 C2 114.9(3) . . ?
C4 C3 C12 123.7(4) . . ?
C2A C3A C12A 120.8(4) . . ?
C4A C3A C2A 119.3(3) . . ?
C4A C3A C12A 119.3(4) . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.9(3) . . ?
C5 C4 H4 120.0 . . ?
C3A C4A H4A 117.3 . . ?
C3A C4A C5A 125.4(3) . . ?
C5A C4A H4A 117.3 . . ?
C4 C5 H5 120.9 . . ?
C6 C5 C4 118.1(3) . . ?
C6 C5 H5 120.9 . . ?
C4A C5A H5A 122.0 . . ?
C4A C5A C6A 116.0(3) . . ?
C6A C5A H5A 122.0 . . ?
C7 C6 C5 120.6(4) . . ?
C7 C6 C11 120.1(5) . . ?
C11 C6 C5 119.2(5) . . ?
C5A C6A C7A 121.6(3) . . ?
C11A C6A C5A 120.7(5) . . ?
C11A C6A C7A 117.4(4) . . ?
C6 C7 H7 117.8 . . ?
C6 C7 C8 124.3(3) . . ?
C8 C7 H7 117.8 . . ?
C6A C7A H7A 117.8 . . ?
C8A C7A C6A 124.3(3) . . ?
C8A C7A H7A 117.8 . . ?
C7 C8 H8 121.9 . . ?
C9 C8 C7 116.2(3) . . ?
C9 C8 H8 121.9 . . ?
C7A C8A H8A 120.7 . . ?
C7A C8A C9A 118.6(3) . . ?
C9A C8A H8A 120.7 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(5) . . ?
C10 C9 H9 119.7 . . ?
C8A C9A H9A 119.7 . . ?
C10A C9A C8A 120.7(4) . . ?
C10A C9A H9A 119.7 . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.3(7) . . ?
C11 C10 H10 119.3 . . ?
C9A C10A H10A 119.7 . . ?
C9A C10A C11A 120.7(7) . . ?
C11A C10A H10A 119.7 . . ?
C6 C11 C12 118.8(6) . . ?
C10 C11 C6 117.3(7) . . ?
C10 C11 C12 123.7(6) . . ?
C6A C11A C10A 118.0(6) . . ?
C6A C11A C12A 120.0(8) . . ?
C10A C11A C12A 121.6(9) . . ?
C3 C12 C11 118.2(6) . . ?
C3 C12 C13 116.8(6) . . ?
C13 C12 C11 124.8(5) . . ?
C3A C12A C11A 116.4(6) . . ?
C13A C12A C3A 116.7(5) . . ?
C13A C12A C11A 126.8(8) . . ?
C12 C13 C24 124.0(3) . . ?
C14 C13 C12 118.5(6) . . ?
C14 C13 C24 117.5(6) . . ?
C12A C13A C24A 123.6(4) . . ?
C40 C13A C12A 119.1(5) . . ?
C40 C13A C24A 117.3(5) . . ?
C1 C14 C13 125.4(4) . . ?
C1 C14 B1 115.4(2) . . ?
C13 C14 B1 118.9(4) . . ?
N1 C15 C16 114.2(3) . . ?
N1 C15 C24 124.8(4) . . ?
C24 C15 C16 121.0(4) . . ?
C24A C15A C16A 121.1(4) . . ?
N1A C15A C16A 113.9(3) . . ?
N1A C15A C24A 125.0(4) . . ?
C15 C16 H16 118.4 . . ?
C17 C16 C15 123.1(3) . . ?
C17 C16 H16 118.4 . . ?
C15A C16A H16A 119.5 . . ?
C15A C16A C17A 121.1(3) . . ?
C17A C16A H16A 119.5 . . ?
C16 C17 H17 122.7 . . ?
C16 C17 C18 114.6(2) . . ?
C18 C17 H17 122.7 . . ?
C16A C17A H17A 123.3 . . ?
C18A C17A C16A 113.3(2) . . ?
C18A C17A H17A 123.3 . . ?
C19 C18 C17 118.9(3) . . ?
C19 C18 C23 119.7(4) . . ?
C23 C18 C17 121.4(4) . . ?
C17A C18A C19A 114.8(3) . . ?
C17A C18A C23A 125.8(4) . . ?
C23A C18A C19A 119.4(5) . . ?
C18 C19 H19 118.4 . . ?
C20 C19 C18 123.3(4) . . ?
C20 C19 H19 118.4 . . ?
C18A C19A H19A 118.4 . . ?
C18A C19A C20A 123.2(4) . . ?
C20A C19A H19A 118.4 . . ?
C19 C20 H20 120.7 . . ?
C19 C20 C21 118.5(3) . . ?
C21 C20 H20 120.7 . . ?
C19A C20A H20A 123.0 . . ?
C21A C20A C19A 113.9(3) . . ?
C21A C20A H20A 123.0 . . ?
C20 C21 H21 120.3 . . ?
C22 C21 C20 119.3(4) . . ?
C22 C21 H21 120.3 . . ?
C20A C21A H21A 117.6 . . ?
C22A C21A C20A 124.8(4) . . ?
C22A C21A H21A 117.6 . . ?
C21 C22 H22 119.0 . . ?
C21 C22 C23 121.9(6) . . ?
C23 C22 H22 119.0 . . ?
C21A C22A H22A 119.9 . . ?
C21A C22A C23A 120.1(6) . . ?
C23A C22A H22A 119.9 . . ?
C18 C23 C24 119.3(6) . . ?
C22 C23 C18 116.8(6) . . ?
C22 C23 C24 123.8(8) . . ?
C18A C23A C22A 118.1(6) . . ?
C18A C23A C24A 119.2(6) . . ?
C22A C23A C24A 122.5(4) . . ?
C15 C24 C13 119.8(6) . . ?
C15 C24 C23 117.3(6) . . ?
C23 C24 C13 122.6(5) . . ?
C15A C24A C13A 118.8(6) . . ?
C15A C24A C23A 116.9(6) . . ?
C23A C24A C13A 123.9(3) . . ?
C26 C25 C30 117.9(6) . . ?
C26 C25 B1 120.3(4) . . ?
C30 C25 B1 121.8(4) . . ?
C25 C26 C31 121.7(6) . . ?
C27 C26 C25 119.2(8) . . ?
C27 C26 C31 119.0(8) . . ?
C26 C27 H27 118.2 . . ?
C28 C27 C26 123.6(11) . . ?
C28 C27 H27 118.2 . . ?
C27 C28 C29 118.5(8) . . ?
C27 C28 C32 123.2(9) . . ?
C29 C28 C32 118.2(10) . . ?
C28 C29 H29 121.1 . . ?
C30 C29 C28 117.8(8) . . ?
C30 C29 H29 121.1 . . ?
C25 C30 C33 119.8(7) . . ?
C29 C30 C25 122.6(7) . . ?
C29 C30 C33 117.2(8) . . ?
C26 C31 H31D 109.5 . . ?
C26 C31 H31E 109.5 . . ?
C26 C31 H31F 109.5 . . ?
H31D C31 H31E 109.5 . . ?
H31D C31 H31F 109.5 . . ?
H31E C31 H31F 109.5 . . ?
C28 C32 H32D 109.5 . . ?
C28 C32 H32E 109.5 . . ?
C28 C32 H32F 109.5 . . ?
H32D C32 H32E 109.5 . . ?
H32D C32 H32F 109.5 . . ?
H32E C32 H32F 109.5 . . ?
C30 C33 H33D 109.5 . . ?
C30 C33 H33E 109.5 . . ?
C30 C33 H33F 109.5 . . ?
H33D C33 H33E 109.5 . . ?
H33D C33 H33F 109.5 . . ?
H33E C33 H33F 109.5 . . ?
C1A C40 C13A 120.7(4) . . ?
C1A C40 B1A 119.1(3) . . ?
C13A C40 B1A 119.8(4) . . ?
C15A N1A H1AA 128(3) . . ?
C15A N1A B1A 120.0(2) . . ?
B1A N1A H1AA 112(3) . . ?
N1 B1 C14 116.8(3) . . ?
N1 B1 C25 118.2(3) . . ?
C14 B1 C25 124.9(3) . . ?
C40 B1A N1A 113.9(2) . . ?
C40 B1A C25A 125.0(3) . . ?
N1A B1A C25A 121.1(3) . . ?
C26A C25A B1A 122.3(5) . . ?
C30A C25A B1A 119.4(5) . . ?
C30A C25A C26A 118.3(6) . . ?
C25A C26A C31A 119.8(7) . . ?
C27A C26A C25A 121.6(9) . . ?
C27A C26A C31A 118.6(8) . . ?
C26A C27A H27A 119.9 . . ?
C26A C27A C28A 120.1(12) . . ?
C28A C27A H27A 119.9 . . ?
C27A C28A C32A 120.1(11) . . ?
C29A C28A C27A 116.5(10) . . ?
C29A C28A C32A 123.2(11) . . ?
C28A C29A H29A 117.6 . . ?
C30A C29A C28A 124.8(10) . . ?
C30A C29A H29A 117.6 . . ?
C25A C30A C33A 122.5(8) . . ?
C29A C30A C25A 117.9(8) . . ?
C29A C30A C33A 119.5(9) . . ?
C26A C31A H31A 109.5 . . ?
C26A C31A H31B 109.5 . . ?
C26A C31A H31C 109.5 . . ?
H31A C31A H31B 109.5 . . ?
H31A C31A H31C 109.5 . . ?
H31B C31A H31C 109.5 . . ?
C28A C32A H32A 109.5 . . ?
C28A C32A H32B 109.5 . . ?
C28A C32A H32C 109.5 . . ?
H32A C32A H32B 109.5 . . ?
H32A C32A H32C 109.5 . . ?
H32B C32A H32C 109.5 . . ?
C30A C33A H33A 109.5 . . ?
C30A C33A H33B 109.5 . . ?
C30A C33A H33C 109.5 . . ?
H33A C33A H33B 109.5 . . ?
H33A C33A H33C 109.5 . . ?
H33B C33A H33C 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
C1A C2A C3A C4A -167.4(2) . . . . ?
C1A C2A C3A C12A 3.5(4) . . . . ?
C1A C40 B1A N1A -175.0(2) . . . . ?
C1A C40 B1A C25A 1.9(4) . . . . ?
N1 C15 C16 C17 177.1(2) . . . . ?
N1 C15 C24 C13 9.7(4) . . . . ?
N1 C15 C24 C23 -163.2(4) . . . . ?
C1 C2 C3 C4 -169.1(2) . . . . ?
C1 C2 C3 C12 4.9(4) . . . . ?
C1 C14 B1 N1 -175.07(19) . . . . ?
C1 C14 B1 C25 0.8(4) . . . . ?
C2 C1 C14 C13 2.8(3) . . . . ?
C2 C1 C14 B1 175.4(2) . . . . ?
C2 C3 C4 C5 176.8(3) . . . . ?
C2 C3 C12 C11 -163.3(3) . . . . ?
C2 C3 C12 C13 11.5(4) . . . . ?
C2A C1A C40 C13A 4.2(4) . . . . ?
C2A C1A C40 B1A 176.8(2) . . . . ?
C2A C3A C4A C5A 177.3(3) . . . . ?
C2A C3A C12A C11A -163.5(4) . . . . ?
C2A C3A C12A C13A 12.9(5) . . . . ?
C3 C4 C5 C6 -12.8(5) . . . . ?
C3 C12 C13 C14 -21.0(4) . . . . ?
C3 C12 C13 C24 159.3(3) . . . . ?
C3A C4A C5A C6A -14.6(5) . . . . ?
C3A C12A C13A C24A 158.8(3) . . . . ?
C3A C12A C13A C40 -21.9(5) . . . . ?
C4 C3 C12 C11 10.1(5) . . . . ?
C4 C3 C12 C13 -175.1(3) . . . . ?
C4 C5 C6 C7 -166.6(3) . . . . ?
C4 C5 C6 C11 9.2(5) . . . . ?
C4A C3A C12A C11A 7.4(5) . . . . ?
C4A C3A C12A C13A -176.1(3) . . . . ?
C4A C5A C6A C7A -165.4(3) . . . . ?
C4A C5A C6A C11A 9.0(6) . . . . ?
C5 C6 C7 C8 175.0(3) . . . . ?
C5 C6 C11 C10 -170.9(4) . . . . ?
C5 C6 C11 C12 3.5(5) . . . . ?
C5A C6A C7A C8A 174.9(3) . . . . ?
C5A C6A C11A C10A -169.6(6) . . . . ?
C5A C6A C11A C12A 3.9(8) . . . . ?
C6 C7 C8 C9 -3.2(4) . . . . ?
C6 C11 C12 C3 -13.2(5) . . . . ?
C6 C11 C12 C13 172.5(3) . . . . ?
C6A C7A C8A C9A -5.2(4) . . . . ?
C6A C11A C12A C3A -12.1(8) . . . . ?
C6A C11A C12A C13A 171.9(5) . . . . ?
C7 C6 C11 C10 4.9(6) . . . . ?
C7 C6 C11 C12 179.3(3) . . . . ?
C7 C8 C9 C10 2.9(5) . . . . ?
C7A C6A C11A C10A 5.1(9) . . . . ?
C7A C6A C11A C12A 178.5(4) . . . . ?
C7A C8A C9A C10A 4.5(6) . . . . ?
C8 C9 C10 C11 1.2(8) . . . . ?
C8A C9A C10A C11A 0.9(10) . . . . ?
C9 C10 C11 C6 -5.1(8) . . . . ?
C9 C10 C11 C12 -179.3(4) . . . . ?
C9A C10A C11A C6A -5.7(12) . . . . ?
C9A C10A C11A C12A -179.1(6) . . . . ?
C10 C11 C12 C3 160.9(4) . . . . ?
C10 C11 C12 C13 -13.5(6) . . . . ?
C10A C11A C12A C3A 161.2(7) . . . . ?
C10A C11A C12A C13A -14.9(10) . . . . ?
C11 C6 C7 C8 -0.8(5) . . . . ?
C11 C12 C13 C14 153.4(3) . . . . ?
C11 C12 C13 C24 -26.3(5) . . . . ?
C11A C6A C7A C8A 0.4(5) . . . . ?
C11A C12A C13A C24A -25.2(6) . . . . ?
C11A C12A C13A C40 154.1(5) . . . . ?
C12 C3 C4 C5 3.0(4) . . . . ?
C12 C13 C14 C1 14.0(4) . . . . ?
C12 C13 C14 B1 -158.3(3) . . . . ?
C12 C13 C24 C15 153.6(3) . . . . ?
C12 C13 C24 C23 -34.0(5) . . . . ?
C12A C3A C4A C5A 6.3(5) . . . . ?
C12A C13A C24A C15A 153.7(3) . . . . ?
C12A C13A C24A C23A -33.2(5) . . . . ?
C12A C13A C40 C1A 13.9(4) . . . . ?
C12A C13A C40 B1A -158.7(3) . . . . ?
C13 C14 B1 N1 -2.0(4) . . . . ?
C13 C14 B1 C25 173.9(3) . . . . ?
C13A C40 B1A N1A -2.4(3) . . . . ?
C13A C40 B1A C25A 174.5(3) . . . . ?
C14 C1 C2 C3 -12.4(3) . . . . ?
C14 C13 C24 C15 -26.2(4) . . . . ?
C14 C13 C24 C23 146.3(4) . . . . ?
C15 N1 B1 C14 -13.9(3) . . . . ?
C15 N1 B1 C25 170.0(2) . . . . ?
C15 C16 C17 C18 -11.8(4) . . . . ?
C15A C16A C17A C18A -9.4(4) . . . . ?
C15A N1A B1A C40 -12.9(3) . . . . ?
C15A N1A B1A C25A 170.1(3) . . . . ?
C16 C15 C24 C13 -170.1(3) . . . . ?
C16 C15 C24 C23 17.0(5) . . . . ?
C16 C17 C18 C19 -168.6(3) . . . . ?
C16 C17 C18 C23 12.6(5) . . . . ?
C16A C15A C24A C13A -171.1(3) . . . . ?
C16A C15A C24A C23A 15.3(4) . . . . ?
C16A C15A N1A B1A -169.4(2) . . . . ?
C16A C17A C18A C19A -170.2(3) . . . . ?
C16A C17A C18A C23A 11.5(4) . . . . ?
C17 C18 C19 C20 -179.7(3) . . . . ?
C17 C18 C23 C22 -175.7(5) . . . . ?
C17 C18 C23 C24 0.7(7) . . . . ?
C17A C18A C19A C20A 179.8(3) . . . . ?
C17A C18A C23A C22A -175.8(4) . . . . ?
C17A C18A C23A C24A -0.4(5) . . . . ?
C18 C19 C20 C21 -5.3(5) . . . . ?
C18 C23 C24 C13 171.7(4) . . . . ?
C18 C23 C24 C15 -15.7(7) . . . . ?
C18A C19A C20A C21A -3.4(4) . . . . ?
C18A C23A C24A C13A 173.2(3) . . . . ?
C18A C23A C24A C15A -13.5(4) . . . . ?
C19 C18 C23 C22 5.5(8) . . . . ?
C19 C18 C23 C24 -178.1(4) . . . . ?
C19 C20 C21 C22 7.0(5) . . . . ?
C19A C18A C23A C22A 5.9(5) . . . . ?
C19A C18A C23A C24A -178.6(3) . . . . ?
C19A C20A C21A C22A 4.8(5) . . . . ?
C20 C21 C22 C23 -2.4(9) . . . . ?
C20A C21A C22A C23A -0.8(7) . . . . ?
C21 C22 C23 C18 -3.7(10) . . . . ?
C21 C22 C23 C24 180.0(5) . . . . ?
C21A C22A C23A C18A -4.8(7) . . . . ?
C21A C22A C23A C24A 180.0(4) . . . . ?
C22 C23 C24 C13 -12.1(8) . . . . ?
C22 C23 C24 C15 160.5(6) . . . . ?
C22A C23A C24A C13A -11.6(5) . . . . ?
C22A C23A C24A C15A 161.7(4) . . . . ?
C23 C18 C19 C20 -0.9(6) . . . . ?
C23A C18A C19A C20A -1.8(5) . . . . ?
C24 C13 C14 C1 -166.2(3) . . . . ?
C24 C13 C14 B1 21.4(4) . . . . ?
C24 C15 C16 C17 -3.0(4) . . . . ?
C24A C13A C40 C1A -166.8(2) . . . . ?
C24A C13A C40 B1A 20.6(4) . . . . ?
C24A C15A C16A C17A -3.9(4) . . . . ?
C24A C15A N1A B1A 8.9(4) . . . . ?
C25 C26 C27 C28 0.3(16) . . . . ?
C26 C25 C30 C29 -1.8(8) . . . . ?
C26 C25 C30 C33 -174.8(5) . . . . ?
C26 C25 B1 N1 -111.7(4) . . . . ?
C26 C25 B1 C14 72.5(5) . . . . ?
C26 C27 C28 C29 3.2(17) . . . . ?
C26 C27 C28 C32 -179.9(13) . . . . ?
C27 C28 C29 C30 -5.7(14) . . . . ?
C28 C29 C30 C25 5.1(12) . . . . ?
C28 C29 C30 C33 178.3(8) . . . . ?
C30 C25 C26 C27 -1.0(9) . . . . ?
C30 C25 C26 C31 -177.9(5) . . . . ?
C30 C25 B1 N1 66.0(5) . . . . ?
C30 C25 B1 C14 -109.8(4) . . . . ?
C31 C26 C27 C28 177.2(11) . . . . ?
C32 C28 C29 C30 177.2(10) . . . . ?
C40 C1A C2A C3A -12.9(3) . . . . ?
C40 C13A C24A C15A -25.7(4) . . . . ?
C40 C13A C24A C23A 147.5(3) . . . . ?
C40 B1A C25A C26A -109.2(5) . . . . ?
C40 B1A C25A C30A 71.5(5) . . . . ?
N1A C15A C16A C17A 174.4(2) . . . . ?
N1A C15A C24A C13A 10.8(4) . . . . ?
N1A C15A C24A C23A -162.9(3) . . . . ?
N1A B1A C25A C26A 67.5(5) . . . . ?
N1A B1A C25A C30A -111.8(4) . . . . ?
B1 N1 C15 C16 -169.7(2) . . . . ?
B1 N1 C15 C24 10.5(3) . . . . ?
B1 C25 C26 C27 176.8(8) . . . . ?
B1 C25 C26 C31 -0.1(8) . . . . ?
B1 C25 C30 C29 -179.5(6) . . . . ?
B1 C25 C30 C33 7.5(7) . . . . ?
B1A C25A C26A C27A -177.6(9) . . . . ?
B1A C25A C26A C31A 3.5(8) . . . . ?
B1A C25A C30A C29A -176.0(8) . . . . ?
B1A C25A C30A C33A 0.2(8) . . . . ?
C25A C26A C27A C28A -2.9(18) . . . . ?
C26A C25A C30A C29A 4.7(10) . . . . ?
C26A C25A C30A C33A -179.1(6) . . . . ?
C26A C27A C28A C29A -2.1(19) . . . . ?
C26A C27A C28A C32A -178.1(14) . . . . ?
C27A C28A C29A C30A 9(2) . . . . ?
C28A C29A C30A C25A -10.5(18) . . . . ?
C28A C29A C30A C33A 173.2(11) . . . . ?
C30A C25A C26A C27A 1.6(12) . . . . ?
C30A C25A C26A C31A -177.3(5) . . . . ?
C31A C26A C27A C28A 175.9(11) . . . . ?
C32A C28A C29A C30A -175.0(13) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in Paratone oil.'
_olex2_submission_original_sample_id KY-461
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.639
_oxdiff_exptl_absorpt_empirical_full_min 0.719
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.7527(12) 13221 12078 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.2473(12) 13198 12078 nmt -1.0003 -0.0001 -0.0000 -0.0005 -0.9998 -0.0000
-0.7746 -0.4716 0.9999

_twin_special_details            
;
Component 2 rotated by -179.9876° 
 around [-0.00 0.00 1.00] (reciprocal) or [-0.35 -0.21 0.91] (direct)
;
####################################################################### 
# 
# 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_ky463_reprocess
_database_code_depnum_ccdc_archive 'CCDC 2084379'
loop_
_audit_author_name
_audit_author_address
'Marina Uzelac'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2021-05-18 deposited with the CCDC.	2022-01-03 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_ky463_reprocess     
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         11 Note
RESPONSE: Reduction of beam stop mask did not yield significant improvement. Most of these missing reflections appeared to be very strong and were treated as overflows.
;
# Added during the CSD deposition process: Tuesday 18 May 2021 09:15 AM
# end Validation Reply Form

_audit_creation_date             2021-04-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H30 B N'
_chemical_formula_sum            'C34 H30 B N'
_chemical_formula_weight         463.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C34 H30 B N'
_chemical_oxdiff_usercomment     '@ 120 K '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.0461(6)
_cell_length_b                   17.1985(5)
_cell_length_c                   13.0700(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.463(5)
_cell_angle_gamma                90
_cell_volume                     2553.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7492
_cell_measurement_temperature    120.1(4)
_cell_measurement_theta_max      23.9510
_cell_measurement_theta_min      3.6690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             984
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_unetI/netI     0.0768
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            55926
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.485
_diffrn_reflns_theta_min         3.406
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.1(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00  43.00   1.00   20.00    --  -15.82  81.00 -68.00   88
  2  ω    -10.00  42.00   1.00   20.00    --   17.54  81.00 -68.00   52
  3  ω    -43.00  46.00   1.00   20.00    --   17.54 -81.00 169.00   89
  4  ω    -88.00 -39.00   1.00   20.00    --  -15.82-178.00 -30.00   49
  5  ω    -39.00  11.00   1.00   20.00    --  -15.82 -77.00  90.00   50
  6  ω    -20.00  56.00   1.00   20.00    --   17.54 -99.00 -90.00   76
  7  ω     -9.00  39.00   1.00   20.00    --   17.54  77.00  30.00   48
  8  ω    -52.00  36.00   1.00   20.00    --   17.54 -38.00 120.00   88
  9  ω    -50.00  34.00   1.00   20.00    --   17.54 -57.00  30.00   84
 10  ω     -9.00  39.00   1.00   20.00    --   17.54  77.00  90.00   48
 11  ω     -1.00  87.00   1.00   20.00    --   17.54  38.00  90.00   88
 12  ω     -9.00  39.00   1.00   20.00    --   17.54  77.00 -30.00   48
 13  ω      1.00  85.00   1.00   20.00    --   17.54  57.00-150.00   84
 14  ω    -20.00  29.00   1.00   20.00    --   17.54 -99.00  90.00   49
 15  ω     -9.00  39.00   1.00   20.00    --   17.54  77.00-120.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0520943000
_diffrn_orient_matrix_UB_12      0.0227106000
_diffrn_orient_matrix_UB_13      0.0141777000
_diffrn_orient_matrix_UB_21      -0.0289719000
_diffrn_orient_matrix_UB_22      0.0275127000
_diffrn_orient_matrix_UB_23      -0.0405494000
_diffrn_orient_matrix_UB_31      -0.0186615000
_diffrn_orient_matrix_UB_32      0.0206868000
_diffrn_orient_matrix_UB_33      0.0383074000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3743
_reflns_number_total             6564
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         6564
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1324
_refine_ls_R_factor_gt           0.0623
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²+0.8045P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1424
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C18(H18), C19(H19), C3(H3), C13(H13), C2(H2), C7(H7), C5(H5),
 C14(H14), C21(H21), C30(H30), C6(H6), C28(H28), C20(H20)
2.b Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C24(H24A,H24B,H24C), C32(H32A,H32B,H32C), C25(H25A,H25B,
 H25C), C33(H33A,H33B,H33C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N1 N 0.26932(15) 0.21893(9) 0.86238(14) 0.0357(4) Uani 1 1 d . . . . .
C10 C 0.41235(16) 0.30656(10) 0.83249(14) 0.0283(4) Uani 1 1 d . . . . .
C4 C 0.61543(17) 0.29850(10) 0.96340(15) 0.0319(4) Uani 1 1 d . . . . .
C9 C 0.53602(17) 0.32302(9) 0.86076(15) 0.0286(4) Uani 1 1 d . . . . .
C8 C 0.58694(17) 0.35801(10) 0.78863(15) 0.0309(4) Uani 1 1 d . . . . .
H8 H 0.538194 0.373065 0.720028 0.037 Uiso 1 1 calc R U . . .
C1 C 0.37884(17) 0.25401(10) 0.89852(15) 0.0308(4) Uani 1 1 d . . . . .
C16 C 0.32318(16) 0.40724(10) 0.68429(15) 0.0294(4) Uani 1 1 d . . . . .
C11 C 0.32182(16) 0.33406(10) 0.73348(15) 0.0287(4) Uani 1 1 d . . . . .
C15 C 0.24284(17) 0.42341(10) 0.58059(15) 0.0317(4) Uani 1 1 d . . . . .
C17 C 0.38679(17) 0.48047(10) 0.72703(15) 0.0301(4) Uani 1 1 d . . . . .
C12 C 0.22146(17) 0.28591(10) 0.68498(15) 0.0307(4) Uani 1 1 d . . . . .
C18 C 0.45735(17) 0.50207(10) 0.83116(16) 0.0318(4) Uani 1 1 d . . . . .
H18 H 0.478869 0.465644 0.886927 0.038 Uiso 1 1 calc R U . . .
C19 C 0.49494(18) 0.57820(10) 0.85057(17) 0.0355(5) Uani 1 1 d . . . . .
H19 H 0.540967 0.593207 0.920137 0.043 Uiso 1 1 calc R U . . .
C26 C 0.09091(17) 0.15873(11) 0.71804(15) 0.0326(5) Uani 1 1 d . . . . .
C3 C 0.57152(18) 0.25557(10) 1.03391(16) 0.0355(5) Uani 1 1 d . . . . .
H3 H 0.621334 0.243174 1.103276 0.043 Uiso 1 1 calc R U . . .
C13 C 0.14031(17) 0.30585(11) 0.58394(15) 0.0334(5) Uani 1 1 d . . . . .
H13 H 0.076061 0.273505 0.552642 0.040 Uiso 1 1 calc R U . . .
C2 C 0.45774(18) 0.23233(10) 1.00146(15) 0.0354(5) Uani 1 1 d . . . . .
H2 H 0.431151 0.201810 1.047297 0.043 Uiso 1 1 calc R U . . .
C22 C 0.35190(18) 0.53651(11) 0.64456(16) 0.0347(5) Uani 1 1 d . . . . .
C7 C 0.70543(18) 0.37028(11) 0.81690(17) 0.0367(5) Uani 1 1 d . . . . .
H7 H 0.735931 0.392774 0.767243 0.044 Uiso 1 1 calc R U . . .
C5 C 0.73673(18) 0.31355(11) 0.99042(17) 0.0379(5) Uani 1 1 d . . . . .
H5 H 0.787550 0.298629 1.058247 0.045 Uiso 1 1 calc R U . . .
C14 C 0.15298(17) 0.37248(11) 0.52916(16) 0.0346(5) Uani 1 1 d . . . . .
H14 H 0.102136 0.382628 0.459393 0.042 Uiso 1 1 calc R U . . .
C27 C 0.11226(17) 0.09029(11) 0.66830(16) 0.0357(5) Uani 1 1 d . . . . .
C21 C 0.3934(2) 0.61204(11) 0.66490(18) 0.0414(5) Uani 1 1 d . . . . .
H21 H 0.373123 0.648718 0.609439 0.050 Uiso 1 1 calc R U . . .
C23 C 0.26459(18) 0.50354(11) 0.54167(16) 0.0371(5) Uani 1 1 d . . . . .
C31 C -0.01327(18) 0.16341(12) 0.74329(16) 0.0362(5) Uani 1 1 d . . . . .
C30 C -0.08954(18) 0.10018(13) 0.72311(16) 0.0403(5) Uani 1 1 d . . . . .
H30 H -0.157840 0.103766 0.741090 0.048 Uiso 1 1 calc R U . . .
C6 C 0.78144(19) 0.34925(11) 0.92009(18) 0.0412(5) Uani 1 1 d . . . . .
H6 H 0.861616 0.359657 0.940135 0.049 Uiso 1 1 calc R U . . .
C28 C 0.03338(19) 0.02884(12) 0.64924(17) 0.0415(5) Uani 1 1 d . . . . .
H28 H 0.048875 -0.015995 0.616563 0.050 Uiso 1 1 calc R U . . .
C29 C -0.06694(19) 0.03207(12) 0.67708(17) 0.0418(5) Uani 1 1 d . . . . .
C20 C 0.46472(19) 0.63255(11) 0.76730(17) 0.0410(5) Uani 1 1 d . . . . .
H20 H 0.492923 0.683177 0.780926 0.049 Uiso 1 1 calc R U . . .
C34 C -0.0425(2) 0.23744(13) 0.79100(18) 0.0508(6) Uani 1 1 d . . . . .
H34A H 0.026210 0.255699 0.847482 0.076 Uiso 1 1 calc R U . . .
H34B H -0.104137 0.227431 0.820596 0.076 Uiso 1 1 calc R U . . .
H34C H -0.068197 0.276244 0.735271 0.076 Uiso 1 1 calc R U . . .
C24 C 0.3196(2) 0.49611(13) 0.45148(17) 0.0493(6) Uani 1 1 d . . . . .
H24A H 0.387998 0.463465 0.476054 0.074 Uiso 1 1 calc R U . . .
H24B H 0.341757 0.546686 0.433929 0.074 Uiso 1 1 calc R U . . .
H24C H 0.263245 0.473546 0.388164 0.074 Uiso 1 1 calc R U . . .
C32 C 0.2229(2) 0.08212(13) 0.64026(19) 0.0482(6) Uani 1 1 d . . . . .
H32A H 0.229526 0.125208 0.595945 0.072 Uiso 1 1 calc R U . . .
H32B H 0.220192 0.034475 0.601211 0.072 Uiso 1 1 calc R U . . .
H32C H 0.289827 0.081439 0.705697 0.072 Uiso 1 1 calc R U . . .
C25 C 0.1518(2) 0.55243(12) 0.50141(19) 0.0512(6) Uani 1 1 d . . . . .
H25A H 0.096864 0.528055 0.438858 0.077 Uiso 1 1 calc R U . . .
H25B H 0.170484 0.603506 0.482355 0.077 Uiso 1 1 calc R U . . .
H25C H 0.117519 0.556320 0.557812 0.077 Uiso 1 1 calc R U . . .
B1 B 0.1932(2) 0.22112(13) 0.75391(18) 0.0328(5) Uani 1 1 d . . . . .
C33 C -0.1489(2) -0.03683(15) 0.6595(2) 0.0666(8) Uani 1 1 d . . . . .
H33A H -0.139985 -0.060970 0.728003 0.100 Uiso 1 1 calc R U . . .
H33B H -0.130001 -0.073673 0.612612 0.100 Uiso 1 1 calc R U . . .
H33C H -0.228729 -0.019647 0.626704 0.100 Uiso 1 1 calc R U . . .
H1 H 0.2559(19) 0.1886(12) 0.9146(18) 0.051(7) Uiso 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
N1 C1 1.383(2) . ?
N1 B1 1.409(3) . ?
N1 H1 0.91(2) . ?
C10 C9 1.438(3) . ?
C10 C1 1.399(3) . ?
C10 C11 1.465(2) . ?
C4 C9 1.427(3) . ?
C4 C3 1.414(3) . ?
C4 C5 1.408(3) . ?
C9 C8 1.419(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.366(3) . ?
C1 C2 1.414(3) . ?
C16 C11 1.416(2) . ?
C16 C15 1.406(3) . ?
C16 C17 1.483(2) . ?
C11 C12 1.428(3) . ?
C15 C14 1.381(3) . ?
C15 C23 1.522(3) . ?
C17 C18 1.393(3) . ?
C17 C22 1.402(3) . ?
C12 C13 1.399(3) . ?
C12 B1 1.541(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.388(3) . ?
C26 C27 1.409(3) . ?
C26 C31 1.402(3) . ?
C26 B1 1.582(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.353(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(3) . ?
C2 H2 0.9300 . ?
C22 C21 1.386(3) . ?
C22 C23 1.514(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.402(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.357(3) . ?
C14 H14 0.9300 . ?
C27 C28 1.387(3) . ?
C27 C32 1.502(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.374(3) . ?
C23 C24 1.538(3) . ?
C23 C25 1.534(3) . ?
C31 C30 1.391(3) . ?
C31 C34 1.510(3) . ?
C30 H30 0.9300 . ?
C30 C29 1.385(3) . ?
C6 H6 0.9300 . ?
C28 H28 0.9300 . ?
C28 C29 1.374(3) . ?
C29 C33 1.510(3) . ?
C20 H20 0.9300 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?

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
C1 N1 B1 123.99(18) . . ?
C1 N1 H1 112.3(14) . . ?
B1 N1 H1 123.2(14) . . ?
C9 C10 C11 124.45(17) . . ?
C1 C10 C9 117.11(16) . . ?
C1 C10 C11 118.07(17) . . ?
C3 C4 C9 119.19(18) . . ?
C5 C4 C9 119.73(19) . . ?
C5 C4 C3 120.99(18) . . ?
C4 C9 C10 119.72(17) . . ?
C8 C9 C10 123.56(17) . . ?
C8 C9 C4 116.56(18) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 C9 121.99(18) . . ?
C7 C8 H8 119.0 . . ?
N1 C1 C10 120.64(17) . . ?
N1 C1 C2 118.18(17) . . ?
C10 C1 C2 121.10(18) . . ?
C11 C16 C17 131.79(17) . . ?
C15 C16 C11 120.34(17) . . ?
C15 C16 C17 107.36(15) . . ?
C16 C11 C10 124.76(17) . . ?
C16 C11 C12 116.76(17) . . ?
C12 C11 C10 118.40(16) . . ?
C16 C15 C23 111.19(16) . . ?
C14 C15 C16 121.34(17) . . ?
C14 C15 C23 127.32(17) . . ?
C18 C17 C16 131.65(16) . . ?
C18 C17 C22 119.78(17) . . ?
C22 C17 C16 108.01(16) . . ?
C11 C12 B1 118.65(17) . . ?
C13 C12 C11 119.92(17) . . ?
C13 C12 B1 120.54(18) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 C17 119.21(18) . . ?
C19 C18 H18 120.4 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.68(19) . . ?
C20 C19 H19 119.7 . . ?
C27 C26 B1 117.35(17) . . ?
C31 C26 C27 118.16(18) . . ?
C31 C26 B1 124.10(18) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 C4 120.65(18) . . ?
C2 C3 H3 119.7 . . ?
C12 C13 H13 119.1 . . ?
C14 C13 C12 121.85(18) . . ?
C14 C13 H13 119.1 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.65(18) . . ?
C3 C2 H2 119.7 . . ?
C17 C22 C23 111.52(16) . . ?
C21 C22 C17 120.03(19) . . ?
C21 C22 C23 128.38(18) . . ?
C8 C7 H7 119.7 . . ?
C8 C7 C6 120.6(2) . . ?
C6 C7 H7 119.7 . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.74(19) . . ?
C6 C5 H5 119.1 . . ?
C15 C14 C13 118.45(18) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C26 C27 C32 120.26(18) . . ?
C28 C27 C26 119.99(19) . . ?
C28 C27 C32 119.69(18) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 C22 119.75(18) . . ?
C20 C21 H21 120.1 . . ?
C15 C23 C24 110.31(16) . . ?
C15 C23 C25 112.31(18) . . ?
C22 C23 C15 100.85(15) . . ?
C22 C23 C24 111.27(18) . . ?
C22 C23 C25 111.90(17) . . ?
C25 C23 C24 109.93(17) . . ?
C26 C31 C34 119.73(19) . . ?
C30 C31 C26 119.79(18) . . ?
C30 C31 C34 120.5(2) . . ?
C31 C30 H30 119.0 . . ?
C29 C30 C31 122.1(2) . . ?
C29 C30 H30 119.0 . . ?
C7 C6 H6 120.4 . . ?
C5 C6 C7 119.3(2) . . ?
C5 C6 H6 120.4 . . ?
C27 C28 H28 118.9 . . ?
C29 C28 C27 122.1(2) . . ?
C29 C28 H28 118.9 . . ?
C30 C29 C33 121.1(2) . . ?
C28 C29 C30 117.82(19) . . ?
C28 C29 C33 121.1(2) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.43(18) . . ?
C21 C20 H20 119.8 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C27 C32 H32A 109.5 . . ?
C27 C32 H32B 109.5 . . ?
C27 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N1 B1 C12 114.26(18) . . ?
N1 B1 C26 117.48(18) . . ?
C12 B1 C26 128.26(18) . . ?
C29 C33 H33A 109.5 . . ?
C29 C33 H33B 109.5 . . ?
C29 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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 169.93(17) . . . . ?
C10 C9 C8 C7 -177.61(17) . . . . ?
C10 C1 C2 C3 -6.9(3) . . . . ?
C10 C11 C12 C13 -172.53(16) . . . . ?
C10 C11 C12 B1 18.2(2) . . . . ?
C4 C9 C8 C7 -2.2(2) . . . . ?
C4 C3 C2 C1 -3.4(3) . . . . ?
C4 C5 C6 C7 -1.4(3) . . . . ?
C9 C10 C1 N1 -162.37(16) . . . . ?
C9 C10 C1 C2 14.4(3) . . . . ?
C9 C10 C11 C16 -35.9(3) . . . . ?
C9 C10 C11 C12 147.30(17) . . . . ?
C9 C4 C3 C2 5.4(3) . . . . ?
C9 C4 C5 C6 -1.7(3) . . . . ?
C9 C8 C7 C6 -0.8(3) . . . . ?
C8 C7 C6 C5 2.7(3) . . . . ?
C1 N1 B1 C12 -18.4(3) . . . . ?
C1 N1 B1 C26 161.85(17) . . . . ?
C1 C10 C9 C4 -12.1(2) . . . . ?
C1 C10 C9 C8 163.11(16) . . . . ?
C1 C10 C11 C16 151.25(18) . . . . ?
C1 C10 C11 C12 -25.5(2) . . . . ?
C16 C11 C12 C13 10.5(3) . . . . ?
C16 C11 C12 B1 -158.84(17) . . . . ?
C16 C15 C14 C13 2.6(3) . . . . ?
C16 C15 C23 C22 -10.2(2) . . . . ?
C16 C15 C23 C24 107.51(19) . . . . ?
C16 C15 C23 C25 -129.47(19) . . . . ?
C16 C17 C18 C19 -172.41(19) . . . . ?
C16 C17 C22 C21 176.43(18) . . . . ?
C16 C17 C22 C23 -0.9(2) . . . . ?
C11 C10 C9 C4 175.01(16) . . . . ?
C11 C10 C9 C8 -9.8(3) . . . . ?
C11 C10 C1 N1 11.0(3) . . . . ?
C11 C10 C1 C2 -172.23(16) . . . . ?
C11 C16 C15 C14 7.1(3) . . . . ?
C11 C16 C15 C23 -177.02(16) . . . . ?
C11 C16 C17 C18 -6.1(4) . . . . ?
C11 C16 C17 C22 -177.36(19) . . . . ?
C11 C12 C13 C14 -1.1(3) . . . . ?
C11 C12 B1 N1 2.8(3) . . . . ?
C11 C12 B1 C26 -177.50(18) . . . . ?
C15 C16 C11 C10 169.81(17) . . . . ?
C15 C16 C11 C12 -13.4(3) . . . . ?
C15 C16 C17 C18 165.5(2) . . . . ?
C15 C16 C17 C22 -5.7(2) . . . . ?
C17 C16 C11 C10 -19.4(3) . . . . ?
C17 C16 C11 C12 157.35(19) . . . . ?
C17 C16 C15 C14 -165.65(17) . . . . ?
C17 C16 C15 C23 10.2(2) . . . . ?
C17 C18 C19 C20 -1.1(3) . . . . ?
C17 C22 C21 C20 -2.8(3) . . . . ?
C17 C22 C23 C15 6.5(2) . . . . ?
C17 C22 C23 C24 -110.52(19) . . . . ?
C17 C22 C23 C25 126.06(19) . . . . ?
C12 C13 C14 C15 -5.6(3) . . . . ?
C18 C17 C22 C21 4.0(3) . . . . ?
C18 C17 C22 C23 -173.34(17) . . . . ?
C18 C19 C20 C21 2.3(3) . . . . ?
C26 C27 C28 C29 0.2(3) . . . . ?
C26 C31 C30 C29 -0.8(3) . . . . ?
C3 C4 C9 C10 2.5(2) . . . . ?
C3 C4 C9 C8 -173.03(16) . . . . ?
C3 C4 C5 C6 174.69(18) . . . . ?
C13 C12 B1 N1 -166.44(17) . . . . ?
C13 C12 B1 C26 13.3(3) . . . . ?
C22 C17 C18 C19 -2.0(3) . . . . ?
C22 C21 C20 C19 -0.3(3) . . . . ?
C5 C4 C9 C10 179.02(16) . . . . ?
C5 C4 C9 C8 3.5(2) . . . . ?
C5 C4 C3 C2 -171.05(17) . . . . ?
C14 C15 C23 C22 165.35(19) . . . . ?
C14 C15 C23 C24 -77.0(3) . . . . ?
C14 C15 C23 C25 46.1(3) . . . . ?
C27 C26 C31 C30 2.6(3) . . . . ?
C27 C26 C31 C34 -176.67(18) . . . . ?
C27 C26 B1 N1 -95.2(2) . . . . ?
C27 C26 B1 C12 85.1(2) . . . . ?
C27 C28 C29 C30 1.6(3) . . . . ?
C27 C28 C29 C33 -177.5(2) . . . . ?
C21 C22 C23 C15 -170.6(2) . . . . ?
C21 C22 C23 C24 72.4(3) . . . . ?
C21 C22 C23 C25 -51.0(3) . . . . ?
C23 C15 C14 C13 -172.54(18) . . . . ?
C23 C22 C21 C20 174.0(2) . . . . ?
C31 C26 C27 C28 -2.3(3) . . . . ?
C31 C26 C27 C32 -179.59(18) . . . . ?
C31 C26 B1 N1 77.4(2) . . . . ?
C31 C26 B1 C12 -102.3(3) . . . . ?
C31 C30 C29 C28 -1.3(3) . . . . ?
C31 C30 C29 C33 177.9(2) . . . . ?
C34 C31 C30 C29 178.45(19) . . . . ?
C32 C27 C28 C29 177.5(2) . . . . ?
B1 N1 C1 C10 11.9(3) . . . . ?
B1 N1 C1 C2 -164.97(18) . . . . ?
B1 C12 C13 C14 167.95(18) . . . . ?
B1 C26 C27 C28 170.76(18) . . . . ?
B1 C26 C27 C32 -6.5(3) . . . . ?
B1 C26 C31 C30 -169.97(18) . . . . ?
B1 C26 C31 C34 10.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.276
_oxdiff_exptl_absorpt_empirical_full_min 0.738
