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

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

data_MI22009
_database_code_depnum_ccdc_archive 'CCDC 2221501'
loop_
_audit_author_name
_audit_author_address
'Gary Stephen Nichol'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-11-22 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;
_audit_creation_date             2022-11-03
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
loop_
_audit_author_email
''
g.s.nichol@ed.ac.uk
_chemical_formula_moiety         'C32 H52 B2 N2 O4'
_chemical_formula_sum            'C32 H52 B2 N2 O4'
_chemical_formula_weight         550.429
_chemical_oxdiff_formula         C32H52B2N2O
_chemical_oxdiff_usercomment     '@ 120 K mji-in-63-r'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
B 0.00141 0.00067 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   9.6072(4)
_cell_length_b                   10.0198(4)
_cell_length_c                   10.2726(4)
_cell_angle_alpha                81.790(3)
_cell_angle_beta                 67.850(4)
_cell_angle_gamma                63.025(4)
_cell_volume                     815.76(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    7228
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      29.6120
_cell_measurement_theta_min      4.0790
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_description       plate
_exptl_crystal_F_000             300.172
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -10 0 0.1229
-12 -11 -3 0.0329
12 10 3 0.0411
-4 -4 11 0.0230
-3 11 -1 0.1348
4 4 -11 0.0246
-1 -10 9 0.0774
13 5 1 0.0648
9 8 13 0.0450
10 1 12 0.0755
-6 -11 -10 0.0797

_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of dichloromethane and hexane  by solvent layering'
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.048
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
3.7103 -10.2492 0.2515 -0.0014 -0.0091 1.0000
-12.2982 -10.6838 -2.6104 -0.3315 -0.9391 0.0905
12.3941 10.4985 2.6201 0.3321 0.9406 -0.0707
-4.2556 -3.6869 10.9471 -0.9800 -0.1823 -0.0802
-3.4722 10.5105 -1.1856 0.0802 0.0166 -0.9966
4.2390 3.7367 -10.9525 0.9803 0.1824 0.0755
-0.9790 -9.6225 9.0851 -0.7965 -0.1493 0.5859
12.8858 5.3627 1.1657 0.4012 0.8413 0.3623
8.8794 7.7861 12.8249 -0.5588 0.8111 -0.1731
10.3691 0.7152 11.7142 -0.5016 0.7301 0.4640
-5.5632 -10.9259 -10.3904 0.4590 -0.6649 0.5893

_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.9949
_diffrn_reflns_Laue_measured_fraction_max 0.9382
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21826
_diffrn_reflns_point_group_measured_fraction_full 0.9949
_diffrn_reflns_point_group_measured_fraction_max 0.9382
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         29.12
_diffrn_reflns_theta_min         3.84
_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 0.9949
_diffrn_measured_fraction_theta_max 0.9382
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     23.00  87.00   1.00   15.00    --   10.76-157.00 -27.00   64
  2  ω      1.00  62.00   1.00   15.00    --   10.76-119.00 128.00   61
  3  ω    -36.00  61.00   1.00   15.00    --   -9.20  57.00 -30.00   97
  4  ω    -42.00  22.00   1.00   15.00    --   -9.20 -77.00  30.00   64
  5  ω    -79.00  17.00   1.00   15.00    --   -9.20 -57.00-180.00   96
  6  ω    -15.00  51.00   1.00   15.00    --   10.76 -99.00  60.00   66
  7  ω    -82.00  13.00   1.00   15.00    --   -9.20 -38.00 -90.00   95
  8  ω    -82.00  13.00   1.00   15.00    --   -9.20 -38.00   0.00   95
  9  ω    -41.00  21.00   1.00   15.00    --   -9.20  77.00 120.00   62
 10  ω    -15.00  31.00   1.00   15.00    --   -9.20 -99.00  60.00   46
 11  ω    -42.00  42.00   1.00   15.00    --   10.76 -77.00-150.00   84
 12  ω    -42.00 -17.00   1.00   15.00    --   -9.20 -77.00  60.00   25
 13  ω    -15.00  51.00   1.00   15.00    --   10.76 -99.00   0.00   66
;
_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      0.0333972000
_diffrn_orient_matrix_UB_12      0.0104306000
_diffrn_orient_matrix_UB_13      -0.0730228000
_diffrn_orient_matrix_UB_21      0.0553664000
_diffrn_orient_matrix_UB_22      0.0212292000
_diffrn_orient_matrix_UB_23      0.0120206000
_diffrn_orient_matrix_UB_31      0.0605425000
_diffrn_orient_matrix_UB_32      -0.0758765000
_diffrn_orient_matrix_UB_33      -0.0093463000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -12
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3302
_reflns_number_total             4116
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-beta (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.2391
_refine_diff_density_min         -0.2303
_refine_diff_density_rms         0.0596
_refine_ls_d_res_high            0.7302
_refine_ls_d_res_low             5.3075
_refine_ls_goodness_of_fit_ref   1.0975
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     415
_refine_ls_number_reflns         4116
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.0975
_refine_ls_shift/su_max          -0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0104P)²+0.0602P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0494
_refine_ls_wR_factor_ref         0.0538
_refine_special_details          
;
#===============================================================================
#>>> 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 ....................       9.92 Note
351_ALERT_3_C Long   C-H (X0.96,N1.08A)  C6       - H6B      .       1.11 Ang.
353_ALERT_3_C Long   N-H (N0.87,N1.01A)  N1       - H1       .       1.01 Ang.
906_ALERT_3_C Large K Value in the Analysis of Variance ......      5.169 Check
910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          8 Note
911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          7 Report

Noted, but no action taken. NoSpherA2 refinement.

#===============================================================================
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         PBE
   BASIS SET:      cc-pVTZ
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2022-11-03_10-14-50
;
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
O1 O 0.88095(6) 0.72937(6) 0.24442(6) 0.01839(14) Uani 1.000000 .
O2 O 1.06426(6) 0.48189(6) 0.20202(6) 0.01971(15) Uani 1.000000 .
N1 N 0.53649(9) 0.79079(7) 0.39604(8) 0.01619(16) Uani 1.000000 .
H1 H 0.6349(12) 0.8156(10) 0.3631(11) 0.035(3) Uani 1.000000 .
C1 C 0.30259(10) 0.67782(10) 0.55916(9) 0.01693(19) Uani 1.000000 .
H1a H 0.2634(10) 0.7975(9) 0.5541(10) 0.031(3) Uani 1.000000 .
C2 C 0.47367(9) 0.57868(8) 0.49277(9) 0.01451(18) Uani 1.000000 .
C3 C 0.59431(9) 0.63399(8) 0.41248(9) 0.01426(18) Uani 1.000000 .
C4 C 0.76299(9) 0.53505(8) 0.35526(9) 0.01498(18) Uani 1.000000 .
C5 C 0.81086(10) 0.37856(9) 0.37111(9) 0.01686(18) Uani 1.000000 .
H5 H 0.9416(10) 0.3034(9) 0.3224(10) 0.032(3) Uani 1.000000 .
C6 C 0.44923(11) 0.85282(9) 0.29496(10) 0.01715(19) Uani 1.000000 .
H6a H 0.3514(11) 0.8148(9) 0.3203(10) 0.030(2) Uani 1.000000 .
H6b H 0.5354(11) 0.8075(9) 0.1876(10) 0.032(2) Uani 1.000000 .
C7 C 0.37216(10) 1.02484(8) 0.29413(9) 0.01735(19) Uani 1.000000 .
C8 C 0.28970(13) 1.07492(12) 0.18306(12) 0.0232(2) Uani 1.000000 .
H8a H 0.2379(12) 1.1954(11) 0.1760(11) 0.045(3) Uani 1.000000 .
H8b H 0.1929(12) 1.0394(10) 0.2087(11) 0.042(3) Uani 1.000000 .
H8c H 0.3775(13) 1.0258(11) 0.0822(12) 0.049(3) Uani 1.000000 .
C9 C 0.23897(13) 1.09239(13) 0.43728(12) 0.0265(2) Uani 1.000000 .
H9a H 0.1890(12) 1.2102(11) 0.4403(11) 0.046(3) Uani 1.000000 .
H9b H 0.2875(13) 1.0530(11) 0.5213(12) 0.049(3) Uani 1.000000 .
H9c H 0.1372(13) 1.0604(12) 0.4607(11) 0.049(3) Uani 1.000000 .
C10 C 0.50811(14) 1.07886(12) 0.25638(14) 0.0263(2) Uani 1.000000 .
H10a H 0.5579(12) 1.0591(11) 0.3364(13) 0.047(3) Uani 1.000000 .
H10b H 0.6078(13) 1.0275(12) 0.1607(12) 0.050(3) Uani 1.000000 .
H10c H 0.4597(13) 1.1974(12) 0.2414(12) 0.053(3) Uani 1.000000 .
C11 C 1.03373(9) 0.72505(9) 0.13589(9) 0.01719(19) Uani 1.000000 .
C12 C 1.16566(10) 0.56391(9) 0.14835(9) 0.01791(19) Uani 1.000000 .
C13 C 1.00448(15) 0.74832(14) -0.00280(12) 0.0269(2) Uani 1.000000 .
H13a H 1.1113(13) 0.7518(11) -0.0886(11) 0.047(3) Uani 1.000000 .
H13b H 0.9805(13) 0.6601(12) -0.0254(12) 0.055(3) Uani 1.000000 .
H13c H 0.8969(14) 0.8538(13) 0.0051(12) 0.055(3) Uani 1.000000 .
C14 C 1.06395(14) 0.85123(12) 0.16679(14) 0.0271(2) Uani 1.000000 .
H14a H 0.9638(13) 0.9579(11) 0.1599(11) 0.044(3) Uani 1.000000 .
H14b H 1.0695(13) 0.8441(11) 0.2727(12) 0.044(3) Uani 1.000000 .
H14c H 1.1825(12) 0.8438(11) 0.0919(12) 0.046(3) Uani 1.000000 .
C15 C 1.30122(13) 0.48956(13) 0.00975(12) 0.0268(2) Uani 1.000000 .
H15a H 1.3883(13) 0.3812(13) 0.0274(12) 0.051(3) Uani 1.000000 .
H15b H 1.2488(12) 0.4779(11) -0.0616(12) 0.050(3) Uani 1.000000 .
H15c H 1.3710(12) 0.5538(11) -0.0373(11) 0.046(3) Uani 1.000000 .
C16 C 1.24049(14) 0.55536(13) 0.25800(13) 0.0273(2) Uani 1.000000 .
H16a H 1.3091(13) 0.4397(11) 0.2773(12) 0.053(3) Uani 1.000000 .
H16b H 1.1449(12) 0.6080(11) 0.3550(12) 0.046(3) Uani 1.000000 .
H16c H 1.3238(12) 0.6098(12) 0.2215(11) 0.050(3) Uani 1.000000 .
B1 B 0.90280(11) 0.58396(10) 0.26732(10) 0.0158(2) Uani 1.000000 .


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 C11 1.4565(9) . ?
O1 B1 1.3727(10) . ?
O2 C12 1.4561(9) . ?
O2 B1 1.3690(10) . ?
N1 H1 1.010(9) . ?
N1 C3 1.4173(10) . ?
N1 C6 1.4720(11) . ?
C1 H1a 1.082(8) . ?
C1 C2 1.4214(10) . ?
C1 C5 1.3691(11) 2_666 ?
C2 C2 1.4248(15) 2_666 ?
C2 C3 1.4360(11) . ?
C3 C4 1.3947(10) . ?
C4 C5 1.4234(11) . ?
C4 B1 1.5544(12) . ?
C5 H5 1.082(8) . ?
C6 H6a 1.099(8) . ?
C6 H6b 1.105(9) . ?
C6 C7 1.5368(11) . ?
C7 C8 1.5293(12) . ?
C7 C9 1.5289(13) . ?
C7 C10 1.5326(13) . ?
C8 H8a 1.080(9) . ?
C8 H8b 1.072(9) . ?
C8 H8c 1.066(11) . ?
C9 H9a 1.053(10) . ?
C9 H9b 1.076(11) . ?
C9 H9c 1.096(11) . ?
C10 H10a 1.052(11) . ?
C10 H10b 1.065(11) . ?
C10 H10c 1.073(10) . ?
C11 C12 1.5610(11) . ?
C11 C13 1.5201(13) . ?
C11 C14 1.5168(12) . ?
C12 C15 1.5175(13) . ?
C12 C16 1.5232(13) . ?
C13 H13a 1.083(11) . ?
C13 H13b 1.083(10) . ?
C13 H13c 1.078(11) . ?
C14 H14a 1.081(10) . ?
C14 H14b 1.100(11) . ?
C14 H14c 1.083(9) . ?
C15 H15a 1.070(11) . ?
C15 H15b 1.077(11) . ?
C15 H15c 1.075(10) . ?
C16 H16a 1.076(10) . ?
C16 H16b 1.065(11) . ?
C16 H16c 1.091(10) . ?

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
B1 O1 C11 107.24(6) . . ?
B1 O2 C12 107.51(6) . . ?
C3 N1 H1 108.9(5) . . ?
C6 N1 H1 107.4(6) . . ?
C6 N1 C3 115.14(7) . . ?
C2 C1 H1a 119.4(4) . . ?
C5 C1 H1a 120.6(4) 2_666 . ?
C5 C1 C2 119.94(8) 2_666 . ?
C2 C2 C1 119.18(9) 2_666 . ?
C3 C2 C1 121.35(7) . . ?
C2 C3 N1 117.92(7) . . ?
C4 C3 N1 121.81(7) . . ?
C4 C3 C2 120.26(7) . . ?
C5 C4 C3 118.62(7) . . ?
B1 C4 C3 124.09(7) . . ?
B1 C4 C5 117.20(7) . . ?
C4 C5 C1 122.33(8) . 2_666 ?
H5 C5 C1 120.1(4) . 2_666 ?
H5 C5 C4 117.5(4) . . ?
H6a C6 N1 109.0(4) . . ?
H6b C6 N1 110.5(5) . . ?
H6b C6 H6a 105.6(7) . . ?
C7 C6 N1 112.69(7) . . ?
C7 C6 H6a 109.9(4) . . ?
C7 C6 H6b 109.0(4) . . ?
C8 C7 C6 107.66(7) . . ?
C9 C7 C6 110.65(8) . . ?
C9 C7 C8 108.78(8) . . ?
C10 C7 C6 110.29(7) . . ?
C10 C7 C8 109.44(8) . . ?
C10 C7 C9 109.99(9) . . ?
H8a C8 C7 110.2(5) . . ?
H8b C8 C7 110.4(6) . . ?
H8b C8 H8a 109.7(7) . . ?
H8c C8 C7 111.1(5) . . ?
H8c C8 H8a 108.6(8) . . ?
H8c C8 H8b 106.7(8) . . ?
H9a C9 C7 111.7(6) . . ?
H9b C9 C7 112.1(5) . . ?
H9b C9 H9a 107.2(8) . . ?
H9c C9 C7 109.9(5) . . ?
H9c C9 H9a 108.7(8) . . ?
H9c C9 H9b 106.9(8) . . ?
H10a C10 C7 112.2(5) . . ?
H10b C10 C7 112.0(6) . . ?
H10b C10 H10a 108.7(8) . . ?
H10c C10 C7 111.4(5) . . ?
H10c C10 H10a 106.1(8) . . ?
H10c C10 H10b 106.2(8) . . ?
C12 C11 O1 102.24(6) . . ?
C13 C11 O1 106.48(7) . . ?
C13 C11 C12 113.26(7) . . ?
C14 C11 O1 108.58(7) . . ?
C14 C11 C12 115.06(7) . . ?
C14 C11 C13 110.45(8) . . ?
C11 C12 O2 102.14(6) . . ?
C15 C12 O2 108.35(7) . . ?
C15 C12 C11 114.60(8) . . ?
C16 C12 O2 106.84(8) . . ?
C16 C12 C11 113.02(7) . . ?
C16 C12 C15 111.11(8) . . ?
H13a C13 C11 110.8(6) . . ?
H13b C13 C11 111.3(6) . . ?
H13b C13 H13a 109.0(8) . . ?
H13c C13 C11 108.2(6) . . ?
H13c C13 H13a 108.8(8) . . ?
H13c C13 H13b 108.6(8) . . ?
H14a C14 C11 109.6(5) . . ?
H14b C14 C11 111.5(5) . . ?
H14b C14 H14a 108.5(8) . . ?
H14c C14 C11 109.4(5) . . ?
H14c C14 H14a 110.2(8) . . ?
H14c C14 H14b 107.7(8) . . ?
H15a C15 C12 110.1(6) . . ?
H15b C15 C12 111.1(5) . . ?
H15b C15 H15a 109.2(8) . . ?
H15c C15 C12 110.0(5) . . ?
H15c C15 H15a 106.5(7) . . ?
H15c C15 H15b 109.9(8) . . ?
H16a C16 C12 109.1(6) . . ?
H16b C16 C12 110.9(6) . . ?
H16b C16 H16a 107.8(8) . . ?
H16c C16 C12 110.6(6) . . ?
H16c C16 H16a 109.5(8) . . ?
H16c C16 H16b 108.9(8) . . ?
O2 B1 O1 112.70(7) . . ?
C4 B1 O1 125.32(7) . . ?
C4 B1 O2 121.98(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C11 C12 O2 27.98(6) . . . . ?
O1 C11 C12 C15 144.89(7) . . . . ?
O1 C11 C12 C16 -86.43(7) . . . . ?
O1 B1 O2 C12 9.36(9) . . . . ?
O1 B1 C4 C3 5.51(11) . . . . ?
O1 B1 C4 C5 -177.96(9) . . . . ?
O2 C12 C11 C13 -86.18(7) . . . . ?
O2 C12 C11 C14 145.45(7) . . . . ?
O2 B1 C4 C3 -173.64(8) . . . . ?
O2 B1 C4 C5 2.88(10) . . . . ?
N1 C3 C2 C1 -2.71(9) . . . . ?
N1 C3 C2 C2 177.74(9) . . . 2_666 ?
N1 C3 C4 C5 -177.42(8) . . . . ?
N1 C3 C4 B1 -0.94(10) . . . . ?
N1 C6 C7 C8 178.57(8) . . . . ?
N1 C6 C7 C9 -62.69(9) . . . . ?
N1 C6 C7 C10 59.23(9) . . . . ?
C1 C2 C2 C1 -180.00(11) . . 2_666 2_666 ?
C1 C2 C2 C3 0.44(9) . . 2_666 2_666 ?
C1 C2 C3 C4 176.22(8) . . . . ?
C1 C5 C4 C3 -0.26(10) 2_666 . . . ?
C1 C5 C4 B1 -176.98(8) 2_666 . . . ?
C2 C2 C3 C4 -3.33(12) 2_666 . . . ?
C2 C3 C4 C5 3.69(9) . . . . ?
C2 C3 C4 B1 -179.84(7) . . . . ?


_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 'mji-in-63-r '
_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 1.366
_oxdiff_exptl_absorpt_empirical_full_min 0.850
####################################################################### 
# 
# 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_mu734_reprocess
_database_code_depnum_ccdc_archive 'CCDC 2221502'
loop_
_audit_author_name
_audit_author_address
'Gary Stephen Nichol'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-11-22 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_mu734_reprocess     
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         12 Note
RESPONSE: Not significant
;
# Added during the CSD deposition process: Tuesday 22 November 2022 04:31 PM
# end Validation Reply Form

_audit_creation_date             2022-11-22
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'B Br4, C H2 Cl2, C22 H21 B N O'
_chemical_formula_sum            'C23 H23 B2 Br4 Cl2 N O'
_chemical_formula_weight         741.58
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.3365(2)
_cell_length_b                   12.5616(4)
_cell_length_c                   15.3464(4)
_cell_angle_alpha                107.814(3)
_cell_angle_beta                 93.035(2)
_cell_angle_gamma                97.768(2)
_cell_volume                     1327.45(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10163
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      28.8650
_cell_measurement_theta_min      3.6940
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.283
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78770
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.855
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_recrystallization_method 
'Crystallised at room temperature from DCM solution.'
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.124
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            29275
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.326
_diffrn_reflns_theta_min         3.451
_diffrn_ambient_temperature      120.00
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  53.00   1.00   30.00    --  -15.66  46.00-138.00   86
  2  ω    -51.00  35.00   1.00   30.00    --   17.38 -46.00  72.00   86
  3  ω      0.00  86.00   1.00   30.00    --   17.38  46.00-138.00   86
  4  ω    -42.00  39.00   1.00   30.00    --  -15.66  77.00 -30.00   81
  5  ω     39.00  90.00   1.00   30.00    --   17.38 178.00  60.00   51
  6  ω      1.00  85.00   1.00   30.00    --   17.38  57.00-120.00   84
  7  ω     -9.00  39.00   1.00   30.00    --   17.38  77.00  90.00   48
  8  ω     -9.00  39.00   1.00   30.00    --   17.38  77.00 -60.00   48
  9  ω      1.00  85.00   1.00   30.00    --   17.38  57.00 120.00   84
 10  ω    -20.00  56.00   1.00   30.00    --   17.38 -99.00 150.00   76
 11  ω    -20.00  56.00   1.00   30.00    --   17.38 -99.00 -90.00   76
 12  ω     -9.00  39.00   1.00   30.00    --   17.38  77.00  30.00   48
 13  ω    -20.00  52.00   1.00   30.00    --   17.38 -99.00  30.00   72
 14  ω     -9.00  39.00   1.00   30.00    --   17.38  77.00   0.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5260
_reflns_number_total             6510
_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 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         6510
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0286
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0204P)²+1.0297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0551
_refine_ls_wR_factor_ref         0.0593
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Br4-B2 \\sim Br4A-B2
 with sigma of 0.02
3. Others
 Sof(Br4A)=1-FVAR(1)
 Sof(Br4)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
4.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C5(H5), C10(H10), C4(H4), C11(H11), C17(H17), C15(H15), C16(H16)
4.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.56397(4) 1.02997(2) 0.62478(2) 0.02048(7) Uani 1 1 d . . . . .
Br3 Br 0.44036(4) 1.17234(2) 0.82394(2) 0.02154(7) Uani 1 1 d . . . . .
Br2 Br 0.68758(5) 0.96877(3) 0.81034(2) 0.03322(8) Uani 1 1 d . . . . .
Br4 Br 0.8751(9) 1.2111(6) 0.7787(4) 0.0239(10) Uani 0.44(4) 1 d D . P A 1
Cl2 Cl 0.80116(11) 0.55961(7) 1.05276(5) 0.0423(2) Uani 1 1 d . . . . .
Cl1 Cl 0.65048(13) 0.50524(8) 0.86220(6) 0.0495(2) Uani 1 1 d . . . . .
O1 O 0.2062(2) 0.66440(14) 0.75320(11) 0.0195(4) Uani 1 1 d . . . . .
N1 N 0.1545(3) 0.8278(2) 0.72842(14) 0.0174(5) Uani 1 1 d . . . . .
C8 C 0.2387(3) 0.5132(2) 0.46327(16) 0.0148(5) Uani 1 1 d . . . . .
B2 B 0.6435(4) 1.0961(3) 0.76000(19) 0.0209(6) Uani 1 1 d D . . . .
C9 C 0.2524(3) 0.4647(2) 0.37030(16) 0.0183(5) Uani 1 1 d . . . . .
H9 H 0.232375 0.506976 0.329835 0.022 Uiso 1 1 calc R U . . .
C13 C 0.2671(3) 0.4473(2) 0.52331(16) 0.0156(5) Uani 1 1 d . . . . .
C1 C 0.1534(3) 0.7874(2) 0.63086(15) 0.0150(5) Uani 1 1 d . . . . .
C3 C 0.1980(3) 0.6301(2) 0.49942(16) 0.0148(5) Uani 1 1 d . . . . .
C5 C 0.1301(3) 0.8070(2) 0.48383(16) 0.0166(5) Uani 1 1 d . . . . .
H5 H 0.108767 0.850358 0.444370 0.020 Uiso 1 1 calc R U . . .
C7 C 0.0736(4) 0.9728(2) 0.61714(17) 0.0209(6) Uani 1 1 d . . . . .
H7A H -0.058252 0.967547 0.626045 0.031 Uiso 1 1 calc R U . . .
H7B H 0.101279 1.015781 0.574538 0.031 Uiso 1 1 calc R U . . .
H7C H 0.147037 1.011425 0.676400 0.031 Uiso 1 1 calc R U . . .
C18 C 0.1806(3) 0.7705(2) 0.78461(16) 0.0185(5) Uani 1 1 d . . . . .
C14 C 0.2543(3) 0.4890(2) 0.62082(16) 0.0169(5) Uani 1 1 d . . . . .
C10 C 0.2949(4) 0.3548(2) 0.33387(17) 0.0220(6) Uani 1 1 d . . . . .
H10 H 0.303459 0.324240 0.269709 0.026 Uiso 1 1 calc R U . . .
C4 C 0.1692(3) 0.6987(2) 0.44493(16) 0.0171(5) Uani 1 1 d . . . . .
H4 H 0.176535 0.670560 0.380490 0.021 Uiso 1 1 calc R U . . .
C12 C 0.3108(3) 0.3366(2) 0.48559(17) 0.0189(5) Uani 1 1 d . . . . .
C2 C 0.1898(3) 0.6770(2) 0.59447(16) 0.0149(5) Uani 1 1 d . . . . .
C11 C 0.3239(3) 0.2922(2) 0.39007(17) 0.0218(6) Uani 1 1 d . . . . .
H11 H 0.353193 0.218195 0.364992 0.026 Uiso 1 1 calc R U . . .
C6 C 0.1204(3) 0.8560(2) 0.57799(16) 0.0157(5) Uani 1 1 d . . . . .
C17 C 0.3416(4) 0.2715(2) 0.54411(18) 0.0221(6) Uani 1 1 d . . . . .
H17 H 0.372057 0.197824 0.518603 0.027 Uiso 1 1 calc R U . . .
C15 C 0.2833(4) 0.4210(2) 0.67438(17) 0.0214(6) Uani 1 1 d . . . . .
H15 H 0.272464 0.448543 0.738525 0.026 Uiso 1 1 calc R U . . .
C19 C 0.1844(4) 0.8194(2) 0.88729(16) 0.0225(6) Uani 1 1 d . . . . .
C16 C 0.3283(4) 0.3123(2) 0.63649(19) 0.0252(6) Uani 1 1 d . . . . .
H16 H 0.349332 0.267474 0.674771 0.030 Uiso 1 1 calc R U . . .
C20 C 0.1893(4) 0.9474(2) 0.91806(17) 0.0273(6) Uani 1 1 d . . . . .
H20A H 0.296749 0.983134 0.896132 0.041 Uiso 1 1 calc R U . . .
H20B H 0.198313 0.976615 0.985370 0.041 Uiso 1 1 calc R U . . .
H20C H 0.075978 0.964806 0.892425 0.041 Uiso 1 1 calc R U . . .
C23 C 0.7055(4) 0.4503(2) 0.95103(19) 0.0317(7) Uani 1 1 d . . . . .
H23A H 0.795229 0.397599 0.931226 0.038 Uiso 1 1 calc R U . . .
H23B H 0.592400 0.407152 0.963613 0.038 Uiso 1 1 calc R U . . .
C21 C 0.3574(5) 0.7918(3) 0.93154(19) 0.0355(7) Uani 1 1 d . . . . .
H21A H 0.353620 0.709509 0.912185 0.053 Uiso 1 1 calc R U . . .
H21B H 0.360435 0.820958 0.998666 0.053 Uiso 1 1 calc R U . . .
H21C H 0.468287 0.827219 0.911971 0.053 Uiso 1 1 calc R U . . .
C22 C 0.0100(5) 0.7613(3) 0.9156(2) 0.0395(8) Uani 1 1 d . . . . .
H22A H -0.099829 0.781428 0.889199 0.059 Uiso 1 1 calc R U . . .
H22B H 0.013281 0.786326 0.982786 0.059 Uiso 1 1 calc R U . . .
H22C H 0.005245 0.678954 0.892762 0.059 Uiso 1 1 calc R U . . .
B1 B 0.2153(4) 0.6095(2) 0.65786(19) 0.0168(6) Uani 1 1 d . . . . .
H1 H 0.145(4) 0.889(2) 0.7497(18) 0.016(8) Uiso 1 1 d . . . . .
Br4A Br 0.8814(9) 1.2025(7) 0.7865(6) 0.0404(8) Uani 0.56(4) 1 d D . 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
Br1 B2 2.006(3) . ?
Br3 B2 2.017(3) . ?
Br2 B2 2.031(3) . ?
Br4 B2 2.022(7) . ?
Cl2 C23 1.768(3) . ?
Cl1 C23 1.758(3) . ?
O1 C18 1.315(3) . ?
O1 B1 1.423(3) . ?
N1 C1 1.425(3) . ?
N1 C18 1.302(3) . ?
N1 H1 0.76(3) . ?
C8 C9 1.384(3) . ?
C8 C13 1.439(3) . ?
C8 C3 1.480(3) . ?
B2 Br4A 1.990(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.406(4) . ?
C13 C14 1.439(3) . ?
C13 C12 1.422(3) . ?
C1 C2 1.396(3) . ?
C1 C6 1.386(3) . ?
C3 C4 1.399(3) . ?
C3 C2 1.404(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.385(3) . ?
C5 C6 1.397(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 C6 1.501(3) . ?
C18 C19 1.503(3) . ?
C14 C15 1.383(3) . ?
C14 B1 1.518(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.360(4) . ?
C4 H4 0.9500 . ?
C12 C11 1.413(3) . ?
C12 C17 1.416(4) . ?
C2 B1 1.493(4) . ?
C11 H11 0.9500 . ?
C17 H17 0.9500 . ?
C17 C16 1.366(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.402(4) . ?
C19 C20 1.526(4) . ?
C19 C21 1.537(4) . ?
C19 C22 1.536(4) . ?
C16 H16 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C18 O1 B1 121.7(2) . . ?
C1 N1 H1 117(2) . . ?
C18 N1 C1 126.2(2) . . ?
C18 N1 H1 117(2) . . ?
C9 C8 C13 118.1(2) . . ?
C9 C8 C3 120.6(2) . . ?
C13 C8 C3 121.3(2) . . ?
Br1 B2 Br3 109.18(14) . . ?
Br1 B2 Br2 108.81(14) . . ?
Br1 B2 Br4 108.6(2) . . ?
Br3 B2 Br2 108.82(14) . . ?
Br3 B2 Br4 109.8(2) . . ?
Br4 B2 Br2 111.6(2) . . ?
Br4A B2 Br1 112.3(3) . . ?
Br4A B2 Br3 111.3(2) . . ?
Br4A B2 Br2 106.3(4) . . ?
C8 C9 H9 119.0 . . ?
C8 C9 C10 122.1(2) . . ?
C10 C9 H9 119.0 . . ?
C8 C13 C14 122.7(2) . . ?
C12 C13 C8 119.1(2) . . ?
C12 C13 C14 118.1(2) . . ?
C2 C1 N1 115.4(2) . . ?
C6 C1 N1 120.9(2) . . ?
C6 C1 C2 123.7(2) . . ?
C4 C3 C8 124.2(2) . . ?
C4 C3 C2 117.1(2) . . ?
C2 C3 C8 118.7(2) . . ?
C4 C5 H5 118.3 . . ?
C4 C5 C6 123.5(2) . . ?
C6 C5 H5 118.3 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
O1 C18 C19 116.0(2) . . ?
N1 C18 O1 120.7(2) . . ?
N1 C18 C19 123.4(2) . . ?
C13 C14 B1 115.8(2) . . ?
C15 C14 C13 119.6(2) . . ?
C15 C14 B1 124.5(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.9 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C11 C12 C13 119.9(2) . . ?
C11 C12 C17 120.4(2) . . ?
C17 C12 C13 119.7(2) . . ?
C1 C2 C3 120.1(2) . . ?
C1 C2 B1 118.9(2) . . ?
C3 C2 B1 120.9(2) . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C1 C6 C5 114.7(2) . . ?
C1 C6 C7 123.5(2) . . ?
C5 C6 C7 121.8(2) . . ?
C12 C17 H17 119.3 . . ?
C16 C17 C12 121.4(2) . . ?
C16 C17 H17 119.3 . . ?
C14 C15 H15 119.1 . . ?
C14 C15 C16 121.7(2) . . ?
C16 C15 H15 119.1 . . ?
C18 C19 C20 111.9(2) . . ?
C18 C19 C21 108.2(2) . . ?
C18 C19 C22 107.3(2) . . ?
C20 C19 C21 109.5(2) . . ?
C20 C19 C22 110.2(2) . . ?
C22 C19 C21 109.7(2) . . ?
C17 C16 C15 119.5(2) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Cl2 C23 H23A 109.4 . . ?
Cl2 C23 H23B 109.4 . . ?
Cl1 C23 Cl2 111.30(17) . . ?
Cl1 C23 H23A 109.4 . . ?
Cl1 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1 B1 C14 122.5(2) . . ?
O1 B1 C2 117.0(2) . . ?
C2 B1 C14 120.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C18 C19 C20 169.5(2) . . . . ?
O1 C18 C19 C21 48.7(3) . . . . ?
O1 C18 C19 C22 -69.5(3) . . . . ?
N1 C1 C2 C3 -177.9(2) . . . . ?
N1 C1 C2 B1 3.4(3) . . . . ?
N1 C1 C6 C5 177.8(2) . . . . ?
N1 C1 C6 C7 -3.6(4) . . . . ?
N1 C18 C19 C20 -10.3(4) . . . . ?
N1 C18 C19 C21 -131.0(3) . . . . ?
N1 C18 C19 C22 110.7(3) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C8 C13 C14 C15 -180.0(2) . . . . ?
C8 C13 C14 B1 -2.1(3) . . . . ?
C8 C13 C12 C11 -0.7(4) . . . . ?
C8 C13 C12 C17 179.1(2) . . . . ?
C8 C3 C4 C5 179.4(2) . . . . ?
C8 C3 C2 C1 179.4(2) . . . . ?
C8 C3 C2 B1 -2.0(3) . . . . ?
C9 C8 C13 C14 -179.4(2) . . . . ?
C9 C8 C13 C12 1.1(3) . . . . ?
C9 C8 C3 C4 0.6(4) . . . . ?
C9 C8 C3 C2 -178.5(2) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C13 C8 C9 C10 -0.8(4) . . . . ?
C13 C8 C3 C4 179.9(2) . . . . ?
C13 C8 C3 C2 0.9(3) . . . . ?
C13 C14 C15 C16 1.1(4) . . . . ?
C13 C14 B1 O1 -177.4(2) . . . . ?
C13 C14 B1 C2 0.9(4) . . . . ?
C13 C12 C11 C10 0.0(4) . . . . ?
C13 C12 C17 C16 0.7(4) . . . . ?
C1 N1 C18 O1 -1.2(4) . . . . ?
C1 N1 C18 C19 178.5(2) . . . . ?
C1 C2 B1 O1 -1.9(4) . . . . ?
C1 C2 B1 C14 179.7(2) . . . . ?
C3 C8 C9 C10 178.6(2) . . . . ?
C3 C8 C13 C14 1.3(4) . . . . ?
C3 C8 C13 C12 -178.3(2) . . . . ?
C3 C2 B1 O1 179.5(2) . . . . ?
C3 C2 B1 C14 1.1(4) . . . . ?
C18 O1 B1 C14 176.9(2) . . . . ?
C18 O1 B1 C2 -1.5(4) . . . . ?
C18 N1 C1 C2 -2.1(4) . . . . ?
C18 N1 C1 C6 178.7(2) . . . . ?
C14 C13 C12 C11 179.7(2) . . . . ?
C14 C13 C12 C17 -0.5(3) . . . . ?
C14 C15 C16 C17 -0.9(4) . . . . ?
C4 C3 C2 C1 0.3(3) . . . . ?
C4 C3 C2 B1 178.9(2) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C4 C5 C6 C7 -178.6(2) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C12 C13 C14 B1 177.5(2) . . . . ?
C12 C17 C16 C15 0.0(4) . . . . ?
C2 C1 C6 C5 -1.3(4) . . . . ?
C2 C1 C6 C7 177.3(2) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
C11 C12 C17 C16 -179.5(2) . . . . ?
C6 C1 C2 C3 1.2(4) . . . . ?
C6 C1 C2 B1 -177.4(2) . . . . ?
C6 C5 C4 C3 1.3(4) . . . . ?
C17 C12 C11 C10 -179.8(2) . . . . ?
C15 C14 B1 O1 0.4(4) . . . . ?
C15 C14 B1 C2 178.7(2) . . . . ?
B1 O1 C18 N1 3.0(4) . . . . ?
B1 O1 C18 C19 -176.7(2) . . . . ?
B1 C14 C15 C16 -176.6(2) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_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
;
####################################################################### 
# 
# 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_si346b
_database_code_depnum_ccdc_archive 'CCDC 2221503'
loop_
_audit_author_name
_audit_author_address
'Gary Stephen Nichol'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-11-22 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;
_audit_creation_date             2022-11-22
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H18 B Br2 N'
_chemical_formula_sum            'C12 H18 B Br2 N'
_chemical_formula_weight         346.90
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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                   15.7521(4)
_cell_length_b                   6.96070(10)
_cell_length_c                   12.1360(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.573(2)
_cell_angle_gamma                90
_cell_volume                     1330.59(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10753
_cell_measurement_temperature    120.01(11)
_cell_measurement_theta_max      28.8700
_cell_measurement_theta_min      3.8830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.065
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54561
_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    1.732
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.514
_exptl_crystal_size_mid          0.259
_exptl_crystal_size_min          0.095
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28453
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.479
_diffrn_reflns_theta_min         3.358
_diffrn_ambient_temperature      120.00
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  15.00   1.00   20.00    --  -15.82 106.00 -97.00   74
  2  ω    -15.00  60.00   1.00   20.00    --   17.54-106.00 163.00   75
  3  ω    -33.00  51.00   1.00   20.00    --  -15.82  57.00-150.00   84
  4  ω    -45.00  56.00   1.00   20.00    --  -15.82  19.00 150.00  101
  5  ω    -39.00  11.00   1.00   20.00    --  -15.82 -77.00   0.00   50
  6  ω    -33.00  51.00   1.00   20.00    --  -15.82  57.00  90.00   84
  7  ω    -83.00   1.00   1.00   20.00    --  -15.82 -57.00 -90.00   84
  8  ω    -88.00 -39.00   1.00   20.00    --  -15.82-178.00 -60.00   49
  9  ω    -88.00 -35.00   1.00   20.00    --  -15.82 178.00-150.00   53
 10  ω    -88.00 -35.00   1.00   20.00    --  -15.82 178.00  60.00   53
 11  ω    -50.00  34.00   1.00   20.00    --   17.54 -57.00 -60.00   84
 12  ω     -9.00  39.00   1.00   20.00    --   17.54  77.00-150.00   48
 13  ω    -85.00   3.00   1.00   20.00    --  -15.82 -38.00 150.00   88
 14  ω     -9.00  16.00   1.00   20.00    --   17.54  77.00 120.00   25
 15  ω     -9.00  39.00   1.00   20.00    --   17.54  77.00 150.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2922
_reflns_number_total             3401
_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 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         3401
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0236
_refine_ls_restrained_S_all      1.048
_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)+(0.0226P)²+0.6776P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0486
_refine_ls_wR_factor_ref         0.0512
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.15138(2) 0.35890(3) 0.48445(2) 0.01832(6) Uani 1 1 d . . . . .
Br2 Br 0.08385(2) 0.46511(3) 0.73306(2) 0.02194(6) Uani 1 1 d . . . . .
N1 N 0.15954(10) 0.7526(2) 0.58236(12) 0.0127(3) Uani 1 1 d . . . . .
C1 C 0.26787(12) 0.5027(3) 0.66014(15) 0.0118(4) Uani 1 1 d . . . . .
C2 C 0.28873(13) 0.3652(3) 0.74102(15) 0.0150(4) Uani 1 1 d . . . . .
H2 H 0.244372 0.296301 0.775828 0.018 Uiso 1 1 calc R U . . .
C3 C 0.37211(13) 0.3274(3) 0.77130(15) 0.0168(4) Uani 1 1 d . . . . .
H3 H 0.384412 0.234194 0.826362 0.020 Uiso 1 1 calc R U . . .
C4 C 0.43763(13) 0.4265(3) 0.72079(16) 0.0169(4) Uani 1 1 d . . . . .
H4 H 0.495063 0.400038 0.740041 0.020 Uiso 1 1 calc R U . . .
C5 C 0.41834(13) 0.5643(3) 0.64201(15) 0.0158(4) Uani 1 1 d . . . . .
H5 H 0.463258 0.632318 0.607878 0.019 Uiso 1 1 calc R U . . .
C6 C 0.33436(12) 0.6059(3) 0.61139(15) 0.0122(4) Uani 1 1 d . . . . .
C7 C 0.31896(12) 0.7628(3) 0.52468(15) 0.0129(4) Uani 1 1 d . . . . .
C8 C 0.22439(12) 0.7982(3) 0.49546(15) 0.0138(4) Uani 1 1 d . . . . .
H8A H 0.217884 0.935149 0.475124 0.017 Uiso 1 1 calc R U . . .
H8B H 0.210325 0.721337 0.429104 0.017 Uiso 1 1 calc R U . . .
C9 C 0.36102(13) 0.9520(3) 0.56194(17) 0.0192(4) Uani 1 1 d . . . . .
H9A H 0.338779 0.989579 0.633923 0.029 Uiso 1 1 calc R U . . .
H9B H 0.348438 1.052977 0.507916 0.029 Uiso 1 1 calc R U . . .
H9C H 0.422602 0.933896 0.567686 0.029 Uiso 1 1 calc R U . . .
C10 C 0.36005(13) 0.6998(3) 0.41551(16) 0.0195(4) Uani 1 1 d . . . . .
H10A H 0.421760 0.691760 0.425546 0.029 Uiso 1 1 calc R U . . .
H10B H 0.346632 0.793897 0.357869 0.029 Uiso 1 1 calc R U . . .
H10C H 0.337847 0.573651 0.393826 0.029 Uiso 1 1 calc R U . . .
C11 C 0.07339(13) 0.7939(3) 0.53247(17) 0.0199(4) Uani 1 1 d . . . . .
H11A H 0.070183 0.929461 0.511091 0.030 Uiso 1 1 calc R U . . .
H11B H 0.029335 0.765991 0.586635 0.030 Uiso 1 1 calc R U . . .
H11C H 0.064652 0.712947 0.467251 0.030 Uiso 1 1 calc R U . . .
C12 C 0.17012(13) 0.8858(3) 0.67912(16) 0.0177(4) Uani 1 1 d . . . . .
H12A H 0.223982 0.858130 0.716981 0.027 Uiso 1 1 calc R U . . .
H12B H 0.123081 0.866989 0.730251 0.027 Uiso 1 1 calc R U . . .
H12C H 0.170177 1.019150 0.653173 0.027 Uiso 1 1 calc R U . . .
B1 B 0.17266(14) 0.5335(3) 0.61986(17) 0.0135(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 B1 2.069(2) . ?
Br2 B1 2.027(2) . ?
N1 C8 1.509(2) . ?
N1 C11 1.508(2) . ?
N1 C12 1.504(2) . ?
N1 B1 1.604(3) . ?
C1 C2 1.408(3) . ?
C1 C6 1.405(3) . ?
C1 B1 1.587(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.401(3) . ?
C6 C7 1.534(2) . ?
C7 C8 1.548(3) . ?
C7 C9 1.540(3) . ?
C7 C10 1.544(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C8 N1 B1 108.17(14) . . ?
C11 N1 C8 106.98(14) . . ?
C11 N1 B1 114.06(15) . . ?
C12 N1 C8 110.22(14) . . ?
C12 N1 C11 106.75(15) . . ?
C12 N1 B1 110.59(14) . . ?
C2 C1 B1 121.31(17) . . ?
C6 C1 C2 118.12(17) . . ?
C6 C1 B1 120.49(16) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.87(18) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.70(17) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.29(18) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.75(18) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C7 122.62(16) . . ?
C5 C6 C1 119.25(17) . . ?
C5 C6 C7 118.14(17) . . ?
C6 C7 C8 114.56(15) . . ?
C6 C7 C9 110.05(15) . . ?
C6 C7 C10 108.76(15) . . ?
C9 C7 C8 109.96(15) . . ?
C9 C7 C10 108.19(16) . . ?
C10 C7 C8 105.04(15) . . ?
N1 C8 C7 117.59(14) . . ?
N1 C8 H8A 107.9 . . ?
N1 C8 H8B 107.9 . . ?
C7 C8 H8A 107.9 . . ?
C7 C8 H8B 107.9 . . ?
H8A C8 H8B 107.2 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Br2 B1 Br1 107.03(10) . . ?
N1 B1 Br1 108.29(12) . . ?
N1 B1 Br2 109.13(13) . . ?
C1 B1 Br1 108.08(13) . . ?
C1 B1 Br2 114.58(13) . . ?
C1 B1 N1 109.52(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.3(3) . . . . ?
C1 C6 C7 C8 0.0(2) . . . . ?
C1 C6 C7 C9 124.54(18) . . . . ?
C1 C6 C7 C10 -117.11(19) . . . . ?
C2 C1 C6 C5 2.0(3) . . . . ?
C2 C1 C6 C7 -178.34(16) . . . . ?
C2 C1 B1 Br1 -91.96(18) . . . . ?
C2 C1 B1 Br2 27.3(2) . . . . ?
C2 C1 B1 N1 150.26(16) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C4 C5 C6 C7 179.11(17) . . . . ?
C5 C6 C7 C8 179.66(16) . . . . ?
C5 C6 C7 C9 -55.8(2) . . . . ?
C5 C6 C7 C10 62.5(2) . . . . ?
C6 C1 C2 C3 -1.3(3) . . . . ?
C6 C1 B1 Br1 84.66(18) . . . . ?
C6 C1 B1 Br2 -156.13(14) . . . . ?
C6 C1 B1 N1 -33.1(2) . . . . ?
C6 C7 C8 N1 27.1(2) . . . . ?
C8 N1 B1 Br1 -61.96(16) . . . . ?
C8 N1 B1 Br2 -178.14(11) . . . . ?
C8 N1 B1 C1 55.69(18) . . . . ?
C9 C7 C8 N1 -97.48(18) . . . . ?
C10 C7 C8 N1 146.32(16) . . . . ?
C11 N1 C8 C7 -178.40(15) . . . . ?
C11 N1 B1 Br1 56.94(18) . . . . ?
C11 N1 B1 Br2 -59.24(17) . . . . ?
C11 N1 B1 C1 174.59(15) . . . . ?
C12 N1 C8 C7 65.9(2) . . . . ?
C12 N1 B1 Br1 177.26(12) . . . . ?
C12 N1 B1 Br2 61.08(17) . . . . ?
C12 N1 B1 C1 -65.09(19) . . . . ?
B1 N1 C8 C7 -55.1(2) . . . . ?
B1 C1 C2 C3 175.37(17) . . . . ?
B1 C1 C6 C5 -174.67(16) . . . . ?
B1 C1 C6 C7 4.9(3) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_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
;
####################################################################### 
# 
# 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_bq2_reprocess
_database_code_depnum_ccdc_archive 'CCDC 2221504'
loop_
_audit_author_name
_audit_author_address
'Gary Stephen Nichol'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-11-22 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_bq2_reprocess       
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         11 Note
RESPONSE: Not significant
;
# Added during the CSD deposition process: Tuesday 22 November 2022 04:31 PM
# end Validation Reply Form

_audit_creation_date             2022-11-22
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'B Br4, C24 H23 B N O, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C24.50 H24 B2 Br4 Cl N O'
_chemical_formula_weight         725.16
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   17.5337(11)
_cell_length_b                   9.0190(3)
_cell_length_c                   18.6811(8)
_cell_angle_alpha                90
_cell_angle_beta                 117.156(6)
_cell_angle_gamma                90
_cell_volume                     2628.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6892
_cell_measurement_temperature    120.01(13)
_cell_measurement_theta_max      25.7550
_cell_measurement_theta_min      3.9100
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.245
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49581
_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 light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1412
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.222
_exptl_crystal_size_min          0.043
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            29847
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.341
_diffrn_reflns_theta_min         3.261
_diffrn_ambient_temperature      120.00
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -41.00  52.00   1.00   20.00    --  -15.66  75.00  81.00   93
  2  ω    -83.00  10.00   1.00   20.00    --  -15.66 -75.00 -46.00   93
  3  ω    -42.00  39.00   1.00   20.00    --  -15.66  77.00 -30.00   81
  4  ω    -88.00 -39.00   1.00   20.00    --  -15.66-178.00 120.00   49
  5  ω     -9.00  39.00   1.00   20.00    --   17.38  77.00 120.00   48
  6  ω     -9.00  39.00   1.00   20.00    --   17.38  77.00 -90.00   48
  7  ω     -9.00  39.00   1.00   20.00    --   17.38  77.00-150.00   48
  8  ω    -32.00  42.00   1.00   20.00    --  -15.66  57.00-120.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4346
_reflns_number_total             6372
_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 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.957
_refine_diff_density_min         -1.261
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         6372
_refine_ls_number_restraints     56
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.020
_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)+(0.0398P)²+9.5171P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1156
_refine_special_details          
'Dichloromethane modelled as disordered over two sites.  Restraints used as elaboratated upon in the embedded CIF.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C25, Cl3}
3. Restrained distances
 Cl2-C26
 1.78 with sigma of 0.02
 Cl3-C26
 1.77 with sigma of 0.02
 Cl2-C26 = Cl3-C26
 1.771 with sigma of 0.01
 Cl1-Cl4
 2.916 with sigma of 0.03
 Cl2-Cl3
 2.916 with sigma of 0.03
 Cl1-C25
 1.78 with sigma of 0.02
 Cl4-C25
 1.77 with sigma of 0.02
 Cl1-C25 = Cl4-C25
 1.771 with sigma of 0.01
 Cl2-Cl3
 2.92 with sigma of 0.04
 Cl1-Cl4
 2.92 with sigma of 0.04
4. Rigid bond restraints
 Cl2, Cl3, C26
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 Cl1, Cl4, C25
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
Cl2 \\sim Cl3 \\sim C26: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
Cl1 \\sim Cl4 \\sim C25: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
Uanis(C25) = Uanis(Cl3)
Uanis(Cl1) = Uanis(C26)
Uanis(Cl4) = Uanis(C25)
Uanis(Cl2) = Uanis(C26)
6. Rigid body (RIGU) restrains
 Cl1, Cl4, C25
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl2, Cl3, C26
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 Fixed Sof: Cl1(0.25) Cl4(0.25) C25(0.25) H25A(0.25) H25B(0.25) Cl2(0.25)
 Cl3(0.25) C26(0.25) H26A(0.25) H26B(0.25)
8.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B), C18(H18A,H18B), C25(H25A,H25B), C26(H26A,H26B)
8.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C3(H3), C10(H10), C9(H9), C16(H16), C15(H15), C2(H2), C4(H4)
8.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.16116(3) 0.10048(6) 0.71609(3) 0.03217(14) Uani 1 1 d . . . . .
Br4 Br 0.29426(4) -0.03548(7) 0.65438(3) 0.04273(17) Uani 1 1 d . . . . .
Br2 Br 0.31016(4) -0.13612(6) 0.83056(3) 0.03555(15) Uani 1 1 d . . . . .
Br3 Br 0.36226(4) 0.20072(7) 0.80455(4) 0.04346(17) Uani 1 1 d . . . . .
B2 B 0.2824(4) 0.0312(6) 0.7513(3) 0.0241(11) Uani 1 1 d . . . . .
O1 O 0.2472(2) 0.4536(4) 0.62015(18) 0.0247(7) Uani 1 1 d . . . . .
N1 N 0.2550(3) 0.3127(5) 0.5220(2) 0.0259(9) Uani 1 1 d . . . . .
C8 C -0.0959(3) 0.2731(6) 0.5231(3) 0.0315(12) Uani 1 1 d . . . . .
H8 H -0.121227 0.201723 0.481384 0.038 Uiso 1 1 calc R U . . .
C6 C 0.0243(3) 0.4271(5) 0.6089(3) 0.0245(10) Uani 1 1 d . . . . .
C17 C 0.1899(4) 0.0811(6) 0.3958(3) 0.0341(12) Uani 1 1 d . . . . .
H17A H 0.171160 0.126524 0.342149 0.041 Uiso 1 1 calc R U . . .
H17B H 0.179959 -0.027096 0.388519 0.041 Uiso 1 1 calc R U . . .
C21 C 0.3828(3) 0.4642(6) 0.6200(3) 0.0326(12) Uani 1 1 d . . . . .
C7 C -0.0118(3) 0.3181(5) 0.5468(3) 0.0235(10) Uani 1 1 d . . . . .
C5 C -0.0258(3) 0.4856(6) 0.6444(3) 0.0302(12) Uani 1 1 d . . . . .
C19 C 0.2972(4) 0.2722(7) 0.4709(3) 0.0384(13) Uani 1 1 d . . . . .
H19A H 0.359364 0.292944 0.500855 0.046 Uiso 1 1 calc R U . . .
H19B H 0.273238 0.334048 0.421707 0.046 Uiso 1 1 calc R U . . .
C24 C 0.3989(4) 0.5572(7) 0.6944(4) 0.0441(15) Uani 1 1 d . . . . .
H24A H 0.358390 0.640204 0.678435 0.066 Uiso 1 1 calc R U . . .
H24B H 0.457639 0.595581 0.718796 0.066 Uiso 1 1 calc R U . . .
H24C H 0.390876 0.495084 0.733508 0.066 Uiso 1 1 calc R U . . .
C11 C 0.0371(3) 0.2549(5) 0.5065(3) 0.0241(10) Uani 1 1 d . . . . .
C3 C 0.0904(4) 0.6505(6) 0.7285(3) 0.0365(13) Uani 1 1 d . . . . .
H3 H 0.112154 0.726848 0.767767 0.044 Uiso 1 1 calc R U . . .
C13 C 0.1702(3) 0.2531(5) 0.4946(3) 0.0222(10) Uani 1 1 d . . . . .
C23 C 0.3944(4) 0.5685(8) 0.5606(4) 0.059(2) Uani 1 1 d . . . . .
H23A H 0.382102 0.514434 0.510994 0.089 Uiso 1 1 calc R U . . .
H23B H 0.453592 0.604957 0.584796 0.089 Uiso 1 1 calc R U . . .
H23C H 0.355006 0.652600 0.548141 0.089 Uiso 1 1 calc R U . . .
C10 C -0.1099(4) 0.4338(6) 0.6192(3) 0.0357(13) Uani 1 1 d . . . . .
H10 H -0.142954 0.470651 0.643845 0.043 Uiso 1 1 calc R U . . .
C1 C 0.1100(3) 0.4828(5) 0.6365(3) 0.0256(11) Uani 1 1 d . . . . .
C22 C 0.4485(4) 0.3365(7) 0.6490(4) 0.0422(14) Uani 1 1 d . . . . .
H22A H 0.430915 0.261984 0.676731 0.063 Uiso 1 1 calc R U . . .
H22B H 0.505088 0.375411 0.686080 0.063 Uiso 1 1 calc R U . . .
H22C H 0.451223 0.290795 0.602620 0.063 Uiso 1 1 calc R U . . .
C9 C -0.1439(4) 0.3310(6) 0.5596(3) 0.0354(13) Uani 1 1 d . . . . .
H9 H -0.201003 0.297847 0.542362 0.042 Uiso 1 1 calc R U . . .
C16 C 0.0050(3) 0.1478(5) 0.4463(3) 0.0274(11) Uani 1 1 d . . . . .
H16 H -0.051463 0.110574 0.428462 0.033 Uiso 1 1 calc R U . . .
C15 C 0.0554(3) 0.0956(6) 0.4127(3) 0.0296(11) Uani 1 1 d . . . . .
H15 H 0.032064 0.021855 0.372051 0.036 Uiso 1 1 calc R U . . .
C20 C 0.2908(3) 0.4042(5) 0.5836(3) 0.0250(10) Uani 1 1 d . . . . .
C12 C 0.1216(3) 0.3052(5) 0.5307(3) 0.0225(10) Uani 1 1 d . . . . .
C14 C 0.1386(3) 0.1447(5) 0.4347(3) 0.0277(11) Uani 1 1 d . . . . .
C2 C 0.1409(3) 0.5923(6) 0.6949(3) 0.0298(11) Uani 1 1 d . . . . .
H2 H 0.197465 0.628642 0.712451 0.036 Uiso 1 1 calc R U . . .
C4 C 0.0097(4) 0.5968(6) 0.7043(3) 0.0363(13) Uani 1 1 d . . . . .
H4 H -0.023709 0.634951 0.728300 0.044 Uiso 1 1 calc R U . . .
C18 C 0.2838(4) 0.1111(7) 0.4477(3) 0.0403(14) Uani 1 1 d . . . . .
H18A H 0.305342 0.048840 0.496675 0.048 Uiso 1 1 calc R U . . .
H18B H 0.316285 0.085111 0.417817 0.048 Uiso 1 1 calc R U . . .
B1 B 0.1608(4) 0.4153(6) 0.5966(3) 0.0240(11) Uani 1 1 d . . . . .
Cl1 Cl 0.4586(6) 0.6327(8) 0.9812(5) 0.0758(19) Uani 0.25 1 d D U P A -2
Cl4 Cl 0.5192(5) 0.3480(8) 0.9988(5) 0.0618(15) Uani 0.25 1 d D U P A -2
C25 C 0.4930(4) 0.5015(7) 0.9312(4) 0.0618(15) Uani 0.25 1 d D U P A -2
H25A H 0.543626 0.537319 0.925982 0.074 Uiso 0.25 1 calc R U P A -2
H25B H 0.446568 0.476404 0.877237 0.074 Uiso 0.25 1 calc R U P A -2
Cl2 Cl 0.4863(7) 0.5293(10) 1.0860(5) 0.0758(19) Uani 0.25 1 d D U P B -1
Cl3 Cl 0.4930(4) 0.5015(7) 0.9312(4) 0.0618(15) Uani 0.25 1 d D U P B -1
C26 C 0.5481(11) 0.481(3) 1.0372(6) 0.0758(19) Uani 0.25 1 d D U P B -1
H26A H 0.566978 0.377151 1.050239 0.091 Uiso 0.25 1 calc R U P B -1
H26B H 0.599997 0.544493 1.058497 0.091 Uiso 0.25 1 calc R U P B -1


_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 B2 2.016(6) . ?
Br4 B2 2.007(5) . ?
Br2 B2 2.012(6) . ?
Br3 B2 2.005(6) . ?
O1 C20 1.315(6) . ?
O1 B1 1.414(6) . ?
N1 C19 1.495(6) . ?
N1 C13 1.437(6) . ?
N1 C20 1.319(6) . ?
C8 H8 0.9500 . ?
C8 C7 1.392(7) . ?
C8 C9 1.404(7) . ?
C6 C7 1.429(7) . ?
C6 C5 1.422(7) . ?
C6 C1 1.439(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C14 1.503(7) . ?
C17 C18 1.506(8) . ?
C21 C24 1.535(8) . ?
C21 C23 1.537(8) . ?
C21 C22 1.542(8) . ?
C21 C20 1.535(7) . ?
C7 C11 1.489(7) . ?
C5 C10 1.407(8) . ?
C5 C4 1.418(8) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C18 1.505(8) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C11 C16 1.391(7) . ?
C11 C12 1.412(7) . ?
C3 H3 0.9500 . ?
C3 C2 1.401(7) . ?
C3 C4 1.362(8) . ?
C13 C12 1.389(6) . ?
C13 C14 1.396(7) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C10 H10 0.9500 . ?
C10 C9 1.360(8) . ?
C1 C2 1.385(7) . ?
C1 B1 1.525(7) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C9 H9 0.9500 . ?
C16 H16 0.9500 . ?
C16 C15 1.381(7) . ?
C15 H15 0.9500 . ?
C15 C14 1.394(7) . ?
C12 B1 1.483(7) . ?
C2 H2 0.9500 . ?
C4 H4 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
Cl1 C25 1.776(8) . ?
Cl4 C25 1.787(8) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
Cl2 C26 1.758(9) . ?
Cl3 C26 1.773(9) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br4 B2 Br1 109.1(3) . . ?
Br4 B2 Br2 110.4(3) . . ?
Br2 B2 Br1 109.8(2) . . ?
Br3 B2 Br1 108.6(3) . . ?
Br3 B2 Br4 109.8(2) . . ?
Br3 B2 Br2 109.1(3) . . ?
C20 O1 B1 123.4(4) . . ?
C13 N1 C19 114.4(4) . . ?
C20 N1 C19 122.1(4) . . ?
C20 N1 C13 123.3(4) . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.3(5) . . ?
C9 C8 H8 119.4 . . ?
C7 C6 C1 122.3(4) . . ?
C5 C6 C7 119.7(5) . . ?
C5 C6 C1 118.0(5) . . ?
H17A C17 H17B 108.2 . . ?
C14 C17 H17A 109.7 . . ?
C14 C17 H17B 109.7 . . ?
C14 C17 C18 109.9(4) . . ?
C18 C17 H17A 109.7 . . ?
C18 C17 H17B 109.7 . . ?
C24 C21 C23 106.8(5) . . ?
C24 C21 C22 106.9(4) . . ?
C23 C21 C22 112.8(5) . . ?
C20 C21 C24 108.4(4) . . ?
C20 C21 C23 110.8(4) . . ?
C20 C21 C22 110.9(4) . . ?
C8 C7 C6 118.1(4) . . ?
C8 C7 C11 119.8(5) . . ?
C6 C7 C11 122.0(4) . . ?
C10 C5 C6 119.8(5) . . ?
C10 C5 C4 121.0(5) . . ?
C4 C5 C6 119.2(5) . . ?
N1 C19 H19A 109.4 . . ?
N1 C19 H19B 109.4 . . ?
N1 C19 C18 111.3(4) . . ?
H19A C19 H19B 108.0 . . ?
C18 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C16 C11 C7 124.1(5) . . ?
C16 C11 C12 117.4(4) . . ?
C12 C11 C7 118.5(4) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C4 C3 C2 119.4(5) . . ?
C12 C13 N1 117.7(4) . . ?
C12 C13 C14 121.3(4) . . ?
C14 C13 N1 121.0(4) . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C5 C10 H10 120.0 . . ?
C9 C10 C5 120.1(5) . . ?
C9 C10 H10 120.0 . . ?
C6 C1 B1 115.6(4) . . ?
C2 C1 C6 120.1(4) . . ?
C2 C1 B1 124.3(5) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.1(5) . . ?
C10 C9 H9 119.5 . . ?
C11 C16 H16 120.1 . . ?
C15 C16 C11 119.8(5) . . ?
C15 C16 H16 120.1 . . ?
C16 C15 H15 118.0 . . ?
C16 C15 C14 123.9(5) . . ?
C14 C15 H15 118.0 . . ?
O1 C20 N1 120.4(4) . . ?
O1 C20 C21 113.2(4) . . ?
N1 C20 C21 126.4(4) . . ?
C11 C12 B1 120.1(4) . . ?
C13 C12 C11 121.5(4) . . ?
C13 C12 B1 118.3(4) . . ?
C13 C14 C17 123.2(5) . . ?
C15 C14 C17 120.8(5) . . ?
C15 C14 C13 116.0(4) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 C3 121.3(5) . . ?
C1 C2 H2 119.3 . . ?
C5 C4 H4 119.0 . . ?
C3 C4 C5 121.9(5) . . ?
C3 C4 H4 119.0 . . ?
C17 C18 H18A 109.7 . . ?
C17 C18 H18B 109.7 . . ?
C19 C18 C17 109.8(5) . . ?
C19 C18 H18A 109.7 . . ?
C19 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
O1 B1 C1 122.1(4) . . ?
O1 B1 C12 116.5(4) . . ?
C12 B1 C1 121.4(5) . . ?
Cl1 C25 Cl4 100.5(5) . . ?
Cl1 C25 H25A 111.7 . . ?
Cl1 C25 H25B 111.7 . . ?
Cl4 C25 H25A 111.7 . . ?
Cl4 C25 H25B 111.7 . . ?
H25A C25 H25B 109.4 . . ?
Cl2 C26 Cl3 113.8(9) . . ?
Cl2 C26 H26A 108.8 . . ?
Cl2 C26 H26B 108.8 . . ?
Cl3 C26 H26A 108.8 . . ?
Cl3 C26 H26B 108.8 . . ?
H26A C26 H26B 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C19 C18 C17 64.1(6) . . . . ?
N1 C13 C12 C11 178.8(4) . . . . ?
N1 C13 C12 B1 -1.7(6) . . . . ?
N1 C13 C14 C17 1.0(7) . . . . ?
N1 C13 C14 C15 -179.7(4) . . . . ?
C8 C7 C11 C16 -1.8(7) . . . . ?
C8 C7 C11 C12 178.7(4) . . . . ?
C6 C7 C11 C16 179.4(4) . . . . ?
C6 C7 C11 C12 -0.1(6) . . . . ?
C6 C5 C10 C9 -1.7(7) . . . . ?
C6 C5 C4 C3 0.6(7) . . . . ?
C6 C1 C2 C3 0.4(7) . . . . ?
C6 C1 B1 O1 -176.9(4) . . . . ?
C6 C1 B1 C12 3.0(7) . . . . ?
C7 C8 C9 C10 0.3(7) . . . . ?
C7 C6 C5 C10 1.1(7) . . . . ?
C7 C6 C5 C4 -178.2(4) . . . . ?
C7 C6 C1 C2 177.7(4) . . . . ?
C7 C6 C1 B1 -1.3(6) . . . . ?
C7 C11 C16 C15 -179.8(4) . . . . ?
C7 C11 C12 C13 -178.7(4) . . . . ?
C7 C11 C12 B1 1.8(6) . . . . ?
C5 C6 C7 C8 0.1(6) . . . . ?
C5 C6 C7 C11 178.9(4) . . . . ?
C5 C6 C1 C2 -1.3(7) . . . . ?
C5 C6 C1 B1 179.6(4) . . . . ?
C5 C10 C9 C8 1.0(7) . . . . ?
C19 N1 C13 C12 -169.6(4) . . . . ?
C19 N1 C13 C14 11.5(6) . . . . ?
C19 N1 C20 O1 170.4(4) . . . . ?
C19 N1 C20 C21 -9.4(7) . . . . ?
C24 C21 C20 O1 4.4(6) . . . . ?
C24 C21 C20 N1 -175.8(5) . . . . ?
C11 C16 C15 C14 -0.6(7) . . . . ?
C11 C12 B1 O1 176.6(4) . . . . ?
C11 C12 B1 C1 -3.3(7) . . . . ?
C13 N1 C19 C18 -43.6(6) . . . . ?
C13 N1 C20 O1 -4.6(7) . . . . ?
C13 N1 C20 C21 175.6(4) . . . . ?
C13 C12 B1 O1 -2.9(6) . . . . ?
C13 C12 B1 C1 177.2(4) . . . . ?
C23 C21 C20 O1 -112.5(5) . . . . ?
C23 C21 C20 N1 67.3(7) . . . . ?
C10 C5 C4 C3 -178.7(5) . . . . ?
C1 C6 C7 C8 -178.9(4) . . . . ?
C1 C6 C7 C11 -0.1(7) . . . . ?
C1 C6 C5 C10 -179.8(4) . . . . ?
C1 C6 C5 C4 0.8(6) . . . . ?
C22 C21 C20 O1 121.5(5) . . . . ?
C22 C21 C20 N1 -58.7(6) . . . . ?
C9 C8 C7 C6 -0.9(7) . . . . ?
C9 C8 C7 C11 -179.7(4) . . . . ?
C16 C11 C12 C13 1.7(7) . . . . ?
C16 C11 C12 B1 -177.8(4) . . . . ?
C16 C15 C14 C17 179.3(5) . . . . ?
C16 C15 C14 C13 0.0(7) . . . . ?
C20 O1 B1 C1 -175.7(4) . . . . ?
C20 O1 B1 C12 4.4(7) . . . . ?
C20 N1 C19 C18 140.9(5) . . . . ?
C20 N1 C13 C12 5.8(7) . . . . ?
C20 N1 C13 C14 -173.2(4) . . . . ?
C12 C11 C16 C15 -0.3(7) . . . . ?
C12 C13 C14 C17 -177.8(4) . . . . ?
C12 C13 C14 C15 1.4(7) . . . . ?
C14 C17 C18 C19 -49.5(6) . . . . ?
C14 C13 C12 C11 -2.3(7) . . . . ?
C14 C13 C12 B1 177.2(4) . . . . ?
C2 C3 C4 C5 -1.6(8) . . . . ?
C2 C1 B1 O1 4.1(7) . . . . ?
C2 C1 B1 C12 -176.0(5) . . . . ?
C4 C5 C10 C9 177.6(5) . . . . ?
C4 C3 C2 C1 1.1(8) . . . . ?
C18 C17 C14 C13 18.6(7) . . . . ?
C18 C17 C14 C15 -160.6(5) . . . . ?
B1 O1 C20 N1 -0.7(7) . . . . ?
B1 O1 C20 C21 179.1(4) . . . . ?
B1 C1 C2 C3 179.3(5) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_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
;
####################################################################### 
# 
# 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_mu699_boh_b_twin_refinalized_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2221505'
loop_
_audit_author_name
_audit_author_address
'Gary Stephen Nichol'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-11-22 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_mu699_boh_b_twin_refinalized_twin1_hklf4 
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         19 Note
RESPONSE: Not significant
;
# Added during the CSD deposition process: Tuesday 22 November 2022 04:31 PM
# end Validation Reply Form

_audit_creation_date             2022-06-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H26 B N O, C H Cl3'
_chemical_formula_sum            'C25 H27 B Cl3 N O'
_chemical_formula_weight         474.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.9253(5)
_cell_length_b                   13.1059(8)
_cell_length_c                   16.0617(6)
_cell_angle_alpha                86.088(4)
_cell_angle_beta                 72.721(3)
_cell_angle_gamma                77.089(4)
_cell_volume                     2336.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9651
_cell_measurement_temperature    120.1(5)
_cell_measurement_theta_max      28.8790
_cell_measurement_theta_min      3.7630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.410
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             992
_exptl_crystal_recrystallization_method 'Crystallised from chloroform at 4 C.'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.109
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0860
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18790
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.412
_diffrn_reflns_theta_min         3.322
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.1(5)
_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 0.907
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00 -26.00   1.00   20.00    --  -15.66 163.00-144.00   62
  2  ω    -64.00   7.00   1.00   20.00    --  -15.66 116.00  67.00   71
  3  ω     26.00  90.00   1.00   20.00    --   17.54-163.00-169.00   64
  4  ω     -7.00  66.00   1.00   20.00    --   17.54-116.00 -20.00   73
  5  ω    -88.00 -35.00   1.00   20.00    --  -15.66 178.00 -60.00   53
  6  ω    -83.00   1.00   1.00   20.00    --  -15.66 -57.00  90.00   84
  7  ω    -32.00  52.00   1.00   20.00    --  -15.66  57.00-150.00   84
  8  ω     -9.00  39.00   1.00   20.00    --   17.54  77.00  90.00   48
  9  ω     -9.00  39.00   1.00   20.00    --   17.54  77.00-120.00   48
 10  ω    -52.00  36.00   1.00   20.00    --   17.54 -38.00  60.00   88
 11  ω      1.00  85.00   1.00   20.00    --   17.54  57.00 -90.00   84
 12  ω      1.00  85.00   1.00   20.00    --   17.54  57.00   0.00   84
 13  ω    -88.00 -35.00   1.00   20.00    --  -15.66 178.00  30.00   53
 14  ω    -20.00  56.00   1.00   20.00    --   17.54 -99.00  60.00   76
 15  ω     -1.00  87.00   1.00   20.00    --   17.54  38.00 150.00   88
 16  ω    -20.00  56.00   1.00   20.00    --   17.54 -99.00-150.00   76
 17  ω     -1.00  87.00   1.00   20.00    --   17.54  38.00-120.00   88
 18  ω     35.00  90.00   1.00   20.00    --   17.54-178.00  90.00   55
 19  ω    -39.00  44.00   1.00   20.00    --   17.54 -77.00-120.00   83
;
_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      0.0095200000
_diffrn_orient_matrix_UB_12      0.0504742000
_diffrn_orient_matrix_UB_13      0.0049900000
_diffrn_orient_matrix_UB_21      -0.0618960000
_diffrn_orient_matrix_UB_22      0.0215766000
_diffrn_orient_matrix_UB_23      0.0057538000
_diffrn_orient_matrix_UB_31      -0.0119648000
_diffrn_orient_matrix_UB_32      -0.0083547000
_diffrn_orient_matrix_UB_33      0.0456170000
_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                12710
_reflns_number_total             18790
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     568
_refine_ls_number_reflns         18790
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      0.961
_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)+(0.0489P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1004
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5659(6)
 0.4341(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Ternary CH refined with riding coordinates:
 C49(H49), C50(H50)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C20(H20A,H20B), C25(H25A,H25B),
 C26(H26A,H26B), C27(H27A,H27B), C44(H44A,H44B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17),
 C30(H30), C31(H31), C35(H35), C36(H36), C37(H37), C39(H39), C40(H40), C41(H41)
3.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C46(H46A,H46B,
 H46C), C47(H47A,H47B,H47C), C48(H48A,H48B,H48C)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(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
B1 B 0.5587(2) 0.2761(2) 1.03259(15) 0.0170(6) Uani 1 1 d . . . . .
C1 C 0.21573(19) 0.40214(19) 1.20029(14) 0.0252(6) Uani 1 1 d . . . . .
H1A H 0.160922 0.352873 1.219090 0.030 Uiso 1 1 calc R U . . .
H1B H 0.199953 0.439681 1.147955 0.030 Uiso 1 1 calc R U . . .
C2 C 0.1885(2) 0.4807(2) 1.27244(15) 0.0297(6) Uani 1 1 d . . . . .
H2A H 0.201642 0.443546 1.325650 0.036 Uiso 1 1 calc R U . . .
H2B H 0.103232 0.517846 1.286323 0.036 Uiso 1 1 calc R U . . .
C3 C 0.2693(2) 0.55947(19) 1.24439(15) 0.0276(6) Uani 1 1 d . . . . .
H3A H 0.228989 0.619372 1.215334 0.033 Uiso 1 1 calc R U . . .
H3B H 0.280243 0.586447 1.296915 0.033 Uiso 1 1 calc R U . . .
C4 C 0.3918(2) 0.51380(18) 1.18294(13) 0.0198(5) Uani 1 1 d . . . . .
C5 C 0.42360(19) 0.41322(17) 1.14969(13) 0.0153(5) Uani 1 1 d . . . . .
C6 C 0.4759(2) 0.57659(18) 1.15500(14) 0.0238(5) Uani 1 1 d . . . . .
H6 H 0.454978 0.646606 1.175466 0.029 Uiso 1 1 calc R U . . .
C7 C 0.5892(2) 0.54045(18) 1.09833(14) 0.0212(5) Uani 1 1 d . . . . .
H7 H 0.645338 0.584728 1.082322 0.025 Uiso 1 1 calc R U . . .
C8 C 0.62110(19) 0.43881(17) 1.06458(13) 0.0163(5) Uani 1 1 d . . . . .
C9 C 0.53578(19) 0.37561(16) 1.08770(13) 0.0153(5) Uani 1 1 d . . . . .
C10 C 0.74349(19) 0.39903(17) 1.00396(13) 0.0170(5) Uani 1 1 d . . . . .
C11 C 0.8344(2) 0.45231(19) 0.99410(14) 0.0231(5) Uani 1 1 d . . . . .
H11 H 0.818455 0.514112 1.027063 0.028 Uiso 1 1 calc R U . . .
C12 C 0.9496(2) 0.4177(2) 0.93678(15) 0.0275(6) Uani 1 1 d . . . . .
H12 H 1.010047 0.456192 0.931755 0.033 Uiso 1 1 calc R U . . .
C13 C 0.9758(2) 0.3300(2) 0.88848(15) 0.0289(6) Uani 1 1 d . . . . .
H13 H 1.053618 0.308552 0.848828 0.035 Uiso 1 1 calc R U . . .
C14 C 0.8880(2) 0.27055(19) 0.89687(14) 0.0225(5) Uani 1 1 d . . . . .
C15 C 0.9130(2) 0.1788(2) 0.84762(16) 0.0307(6) Uani 1 1 d . . . . .
H15 H 0.991163 0.155840 0.808829 0.037 Uiso 1 1 calc R U . . .
C16 C 0.8269(2) 0.1222(2) 0.85456(15) 0.0304(6) Uani 1 1 d . . . . .
H16 H 0.844755 0.061401 0.820010 0.037 Uiso 1 1 calc R U . . .
C17 C 0.7128(2) 0.15469(18) 0.91290(14) 0.0236(5) Uani 1 1 d . . . . .
H17 H 0.653722 0.114842 0.917656 0.028 Uiso 1 1 calc R U . . .
C18 C 0.6832(2) 0.24276(18) 0.96383(13) 0.0172(5) Uani 1 1 d . . . . .
C19 C 0.77045(19) 0.30403(17) 0.95557(13) 0.0168(5) Uani 1 1 d . . . . .
C20 C 0.3747(2) 0.27158(18) 1.24632(13) 0.0193(5) Uani 1 1 d . . . . .
H20A H 0.365565 0.315738 1.296520 0.023 Uiso 1 1 calc R U . . .
H20B H 0.461165 0.238743 1.223902 0.023 Uiso 1 1 calc R U . . .
C21 C 0.3062(2) 0.18326(19) 1.28114(14) 0.0224(5) Uani 1 1 d . . . . .
C22 C 0.1890(2) 0.2200(2) 1.35417(15) 0.0319(6) Uani 1 1 d . . . . .
H22A H 0.206195 0.253413 1.400398 0.048 Uiso 1 1 calc R U . . .
H22B H 0.153912 0.159617 1.378216 0.048 Uiso 1 1 calc R U . . .
H22C H 0.132090 0.270361 1.330438 0.048 Uiso 1 1 calc R U . . .
C23 C 0.3902(2) 0.1014(2) 1.32043(16) 0.0314(6) Uani 1 1 d . . . . .
H23A H 0.463856 0.073093 1.274484 0.047 Uiso 1 1 calc R U . . .
H23B H 0.349790 0.044512 1.346439 0.047 Uiso 1 1 calc R U . . .
H23C H 0.410527 0.134221 1.365450 0.047 Uiso 1 1 calc R U . . .
C24 C 0.2800(2) 0.1310(2) 1.20821(16) 0.0305(6) Uani 1 1 d . . . . .
H24A H 0.225989 0.182263 1.182652 0.046 Uiso 1 1 calc R U . . .
H24B H 0.241806 0.072356 1.232445 0.046 Uiso 1 1 calc R U . . .
H24C H 0.355434 0.105141 1.163035 0.046 Uiso 1 1 calc R U . . .
N1 N 0.34120(15) 0.34212(14) 1.17702(11) 0.0179(4) Uani 1 1 d . . . . .
O1 O 0.47270(13) 0.22118(12) 1.03921(9) 0.0222(4) Uani 1 1 d . . . . .
H1 H 0.410629 0.246948 1.078898 0.033 Uiso 1 1 calc R U . . .
B2 B 0.5601(2) 0.24455(19) 1.45435(15) 0.0153(5) Uani 1 1 d . . . . .
C25 C 0.85708(19) 0.36270(17) 1.30031(14) 0.0185(5) Uani 1 1 d . . . . .
H25A H 0.932042 0.309666 1.277284 0.022 Uiso 1 1 calc R U . . .
H25B H 0.859467 0.389444 1.355796 0.022 Uiso 1 1 calc R U . . .
C26 C 0.8523(2) 0.45253(17) 1.23550(14) 0.0202(5) Uani 1 1 d . . . . .
H26A H 0.850834 0.426466 1.179490 0.024 Uiso 1 1 calc R U . . .
H26B H 0.924815 0.482150 1.224506 0.024 Uiso 1 1 calc R U . . .
C27 C 0.7403(2) 0.53708(18) 1.27167(14) 0.0204(5) Uani 1 1 d . . . . .
H27A H 0.759129 0.586109 1.307208 0.025 Uiso 1 1 calc R U . . .
H27B H 0.717659 0.577202 1.222479 0.025 Uiso 1 1 calc R U . . .
C28 C 0.6343(2) 0.49405(17) 1.32712(13) 0.0154(5) Uani 1 1 d . . . . .
C29 C 0.64148(18) 0.38923(16) 1.35085(12) 0.0142(5) Uani 1 1 d . . . . .
C30 C 0.5233(2) 0.56281(17) 1.36046(13) 0.0178(5) Uani 1 1 d . . . . .
H30 H 0.516379 0.635197 1.346767 0.021 Uiso 1 1 calc R U . . .
C31 C 0.4241(2) 0.52886(17) 1.41243(13) 0.0174(5) Uani 1 1 d . . . . .
H31 H 0.349738 0.577590 1.432219 0.021 Uiso 1 1 calc R U . . .
C32 C 0.43132(19) 0.42320(16) 1.43657(13) 0.0150(5) Uani 1 1 d . . . . .
C33 C 0.54340(18) 0.35266(16) 1.40817(12) 0.0135(5) Uani 1 1 d . . . . .
C34 C 0.32310(19) 0.38627(16) 1.49219(13) 0.0157(5) Uani 1 1 d . . . . .
C35 C 0.20952(19) 0.44922(18) 1.50599(14) 0.0196(5) Uani 1 1 d . . . . .
H35 H 0.201255 0.516355 1.479301 0.024 Uiso 1 1 calc R U . . .
C36 C 0.1059(2) 0.41718(19) 1.55819(14) 0.0233(6) Uani 1 1 d . . . . .
H36 H 0.029338 0.462729 1.566511 0.028 Uiso 1 1 calc R U . . .
C37 C 0.1146(2) 0.32152(19) 1.59676(14) 0.0229(5) Uani 1 1 d . . . . .
H37 H 0.044227 0.300942 1.632684 0.027 Uiso 1 1 calc R U . . .
C38 C 0.22770(19) 0.25225(17) 1.58388(13) 0.0178(5) Uani 1 1 d . . . . .
C39 C 0.2380(2) 0.15183(19) 1.62169(15) 0.0237(6) Uani 1 1 d . . . . .
H39 H 0.167601 0.130241 1.656474 0.028 Uiso 1 1 calc R U . . .
C40 C 0.3475(2) 0.08450(19) 1.60931(14) 0.0242(5) Uani 1 1 d . . . . .
H40 H 0.353172 0.016926 1.635293 0.029 Uiso 1 1 calc R U . . .
C41 C 0.4518(2) 0.11676(17) 1.55757(13) 0.0185(5) Uani 1 1 d . . . . .
H41 H 0.527694 0.070355 1.549752 0.022 Uiso 1 1 calc R U . . .
C42 C 0.44667(19) 0.21390(17) 1.51789(13) 0.0149(5) Uani 1 1 d . . . . .
C43 C 0.33363(19) 0.28407(17) 1.53093(13) 0.0146(5) Uani 1 1 d . . . . .
C44 C 0.74612(18) 0.25733(16) 1.24181(13) 0.0165(5) Uani 1 1 d . . . . .
H44A H 0.739998 0.309661 1.195027 0.020 Uiso 1 1 calc R U . . .
H44B H 0.670166 0.231984 1.260037 0.020 Uiso 1 1 calc R U . . .
C45 C 0.84930(19) 0.16365(18) 1.20176(13) 0.0192(5) Uani 1 1 d . . . . .
C46 C 0.9541(2) 0.1979(2) 1.13181(14) 0.0277(6) Uani 1 1 d . . . . .
H46A H 0.923495 0.239881 1.087243 0.042 Uiso 1 1 calc R U . . .
H46B H 1.013416 0.135804 1.104650 0.042 Uiso 1 1 calc R U . . .
H46C H 0.992182 0.239784 1.159036 0.042 Uiso 1 1 calc R U . . .
C47 C 0.8957(2) 0.09735(18) 1.27159(15) 0.0216(5) Uani 1 1 d . . . . .
H47A H 0.931093 0.139412 1.300838 0.032 Uiso 1 1 calc R U . . .
H47B H 0.956801 0.036384 1.244223 0.032 Uiso 1 1 calc R U . . .
H47C H 0.828800 0.073761 1.314464 0.032 Uiso 1 1 calc R U . . .
C48 C 0.7946(2) 0.09654(19) 1.15634(16) 0.0290(6) Uani 1 1 d . . . . .
H48A H 0.730865 0.069645 1.199845 0.044 Uiso 1 1 calc R U . . .
H48B H 0.857206 0.037765 1.126615 0.044 Uiso 1 1 calc R U . . .
H48C H 0.760736 0.139376 1.113588 0.044 Uiso 1 1 calc R U . . .
N2 N 0.75369(15) 0.31248(13) 1.31769(10) 0.0143(4) Uani 1 1 d . . . . .
O2 O 0.67002(12) 0.18072(11) 1.44381(9) 0.0183(3) Uani 1 1 d . . . . .
H2 H 0.722304 0.207342 1.407367 0.027 Uiso 1 1 calc R U . . .
C49 C 0.8278(2) 0.13888(18) 0.57042(15) 0.0241(5) Uani 1 1 d . . . . .
H49 H 0.805581 0.099746 0.528516 0.029 Uiso 1 1 calc R U . . .
Cl1 Cl 0.69843(6) 0.18381(5) 0.65643(4) 0.03573(17) Uani 1 1 d . . . . .
Cl2 Cl 0.93644(6) 0.05286(5) 0.61043(4) 0.03841(18) Uani 1 1 d . . . . .
Cl3 Cl 0.88755(6) 0.24387(6) 0.51466(5) 0.03838(18) Uani 1 1 d . . . . .
C50 C 0.3691(2) 0.15982(19) 0.90446(15) 0.0257(6) Uani 1 1 d . . . . .
H50 H 0.427833 0.191802 0.921340 0.031 Uiso 1 1 calc R U . . .
Cl4 Cl 0.38938(8) 0.18018(6) 0.79220(4) 0.0528(2) Uani 1 1 d . . . . .
Cl5 Cl 0.39923(8) 0.02625(5) 0.92709(5) 0.0500(2) Uani 1 1 d . . . . .
Cl6 Cl 0.22428(7) 0.22226(7) 0.96357(5) 0.0578(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 C9 1.554(3) . ?
B1 C18 1.554(3) . ?
B1 O1 1.355(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.516(3) . ?
C1 N1 1.476(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.524(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.516(3) . ?
C4 C5 1.385(3) . ?
C4 C6 1.391(3) . ?
C5 C9 1.416(3) . ?
C5 N1 1.457(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.401(3) . ?
C8 C9 1.403(3) . ?
C8 C10 1.495(3) . ?
C10 C11 1.382(3) . ?
C10 C19 1.436(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.403(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.355(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.410(3) . ?
C14 C15 1.410(3) . ?
C14 C19 1.429(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.371(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.396(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.379(3) . ?
C18 C19 1.422(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.543(3) . ?
C20 N1 1.487(3) . ?
C21 C22 1.538(3) . ?
C21 C23 1.535(3) . ?
C21 C24 1.537(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O1 H1 0.8400 . ?
B2 C33 1.554(3) . ?
B2 C42 1.549(3) . ?
B2 O2 1.358(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.520(3) . ?
C25 N2 1.471(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.521(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.514(3) . ?
C28 C29 1.391(3) . ?
C28 C30 1.400(3) . ?
C29 C33 1.413(3) . ?
C29 N2 1.461(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.376(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.403(3) . ?
C32 C33 1.412(3) . ?
C32 C34 1.494(3) . ?
C34 C35 1.383(3) . ?
C34 C43 1.433(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.405(3) . ?
C36 H36 0.9500 . ?
C36 C37 1.357(3) . ?
C37 H37 0.9500 . ?
C37 C38 1.414(3) . ?
C38 C39 1.407(3) . ?
C38 C43 1.429(3) . ?
C39 H39 0.9500 . ?
C39 C40 1.371(3) . ?
C40 H40 0.9500 . ?
C40 C41 1.410(3) . ?
C41 H41 0.9500 . ?
C41 C42 1.381(3) . ?
C42 C43 1.418(3) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C44 C45 1.548(3) . ?
C44 N2 1.494(3) . ?
C45 C46 1.541(3) . ?
C45 C47 1.530(3) . ?
C45 C48 1.536(3) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
O2 H2 0.8400 . ?
C49 H49 1.0000 . ?
C49 Cl1 1.753(2) . ?
C49 Cl2 1.762(2) . ?
C49 Cl3 1.759(2) . ?
C50 H50 1.0000 . ?
C50 Cl4 1.756(2) . ?
C50 Cl5 1.742(2) . ?
C50 Cl6 1.747(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 B1 C18 118.1(2) . . ?
O1 B1 C9 122.5(2) . . ?
O1 B1 C18 119.3(2) . . ?
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
N1 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
N1 C1 C2 112.73(18) . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
C1 C2 C3 110.3(2) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 C2 113.3(2) . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C5 C4 C3 123.4(2) . . ?
C5 C4 C6 117.5(2) . . ?
C6 C4 C3 119.0(2) . . ?
C4 C5 C9 121.9(2) . . ?
C4 C5 N1 120.73(19) . . ?
C9 C5 N1 117.38(18) . . ?
C4 C6 H6 118.9 . . ?
C7 C6 C4 122.2(2) . . ?
C7 C6 H6 118.9 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C9 118.9(2) . . ?
C7 C8 C10 120.5(2) . . ?
C9 C8 C10 120.64(19) . . ?
C5 C9 B1 121.7(2) . . ?
C8 C9 B1 118.32(19) . . ?
C8 C9 C5 119.08(19) . . ?
C11 C10 C8 120.6(2) . . ?
C11 C10 C19 118.2(2) . . ?
C19 C10 C8 121.20(19) . . ?
C10 C11 H11 119.1 . . ?
C10 C11 C12 121.9(2) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.3(2) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C19 119.7(2) . . ?
C15 C14 C13 121.4(2) . . ?
C15 C14 C19 118.9(2) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.4(2) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.4(2) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 118.9 . . ?
C18 C17 C16 122.1(2) . . ?
C18 C17 H17 118.9 . . ?
C17 C18 B1 122.5(2) . . ?
C17 C18 C19 119.2(2) . . ?
C19 C18 B1 118.3(2) . . ?
C14 C19 C10 119.1(2) . . ?
C18 C19 C10 121.9(2) . . ?
C18 C19 C14 119.0(2) . . ?
H20A C20 H20B 107.1 . . ?
C21 C20 H20A 107.6 . . ?
C21 C20 H20B 107.6 . . ?
N1 C20 H20A 107.6 . . ?
N1 C20 H20B 107.6 . . ?
N1 C20 C21 118.77(17) . . ?
C22 C21 C20 112.90(19) . . ?
C23 C21 C20 105.61(18) . . ?
C23 C21 C22 107.56(19) . . ?
C23 C21 C24 108.45(19) . . ?
C24 C21 C20 112.23(18) . . ?
C24 C21 C22 109.81(19) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 N1 C20 115.46(17) . . ?
C5 N1 C1 110.00(17) . . ?
C5 N1 C20 109.00(15) . . ?
B1 O1 H1 109.5 . . ?
C42 B2 C33 117.44(19) . . ?
O2 B2 C33 122.1(2) . . ?
O2 B2 C42 120.4(2) . . ?
H25A C25 H25B 107.8 . . ?
C26 C25 H25A 109.0 . . ?
C26 C25 H25B 109.0 . . ?
N2 C25 H25A 109.0 . . ?
N2 C25 H25B 109.0 . . ?
N2 C25 C26 112.76(17) . . ?
C25 C26 H26A 109.7 . . ?
C25 C26 H26B 109.7 . . ?
C25 C26 C27 109.76(18) . . ?
H26A C26 H26B 108.2 . . ?
C27 C26 H26A 109.7 . . ?
C27 C26 H26B 109.7 . . ?
C26 C27 H27A 108.9 . . ?
C26 C27 H27B 108.9 . . ?
H27A C27 H27B 107.7 . . ?
C28 C27 C26 113.28(19) . . ?
C28 C27 H27A 108.9 . . ?
C28 C27 H27B 108.9 . . ?
C29 C28 C27 123.6(2) . . ?
C29 C28 C30 117.1(2) . . ?
C30 C28 C27 119.28(19) . . ?
C28 C29 C33 122.3(2) . . ?
C28 C29 N2 120.31(19) . . ?
C33 C29 N2 117.36(18) . . ?
C28 C30 H30 119.0 . . ?
C31 C30 C28 122.1(2) . . ?
C31 C30 H30 119.0 . . ?
C30 C31 H31 119.6 . . ?
C30 C31 C32 120.9(2) . . ?
C32 C31 H31 119.6 . . ?
C31 C32 C33 118.6(2) . . ?
C31 C32 C34 120.76(19) . . ?
C33 C32 C34 120.63(19) . . ?
C29 C33 B2 121.92(19) . . ?
C32 C33 B2 118.26(19) . . ?
C32 C33 C29 118.81(19) . . ?
C35 C34 C32 120.67(19) . . ?
C35 C34 C43 118.2(2) . . ?
C43 C34 C32 121.13(19) . . ?
C34 C35 H35 118.9 . . ?
C34 C35 C36 122.2(2) . . ?
C36 C35 H35 118.9 . . ?
C35 C36 H36 119.8 . . ?
C37 C36 C35 120.3(2) . . ?
C37 C36 H36 119.8 . . ?
C36 C37 H37 119.8 . . ?
C36 C37 C38 120.5(2) . . ?
C38 C37 H37 119.8 . . ?
C37 C38 C43 119.6(2) . . ?
C39 C38 C37 121.2(2) . . ?
C39 C38 C43 119.2(2) . . ?
C38 C39 H39 119.3 . . ?
C40 C39 C38 121.3(2) . . ?
C40 C39 H39 119.3 . . ?
C39 C40 H40 120.4 . . ?
C39 C40 C41 119.2(2) . . ?
C41 C40 H40 120.4 . . ?
C40 C41 H41 119.0 . . ?
C42 C41 C40 121.9(2) . . ?
C42 C41 H41 119.0 . . ?
C41 C42 B2 121.4(2) . . ?
C41 C42 C43 119.1(2) . . ?
C43 C42 B2 119.35(19) . . ?
C38 C43 C34 119.17(19) . . ?
C42 C43 C34 121.5(2) . . ?
C42 C43 C38 119.3(2) . . ?
H44A C44 H44B 107.1 . . ?
C45 C44 H44A 107.8 . . ?
C45 C44 H44B 107.8 . . ?
N2 C44 H44A 107.8 . . ?
N2 C44 H44B 107.8 . . ?
N2 C44 C45 118.17(16) . . ?
C46 C45 C44 112.56(19) . . ?
C47 C45 C44 111.91(17) . . ?
C47 C45 C46 110.19(18) . . ?
C47 C45 C48 108.82(19) . . ?
C48 C45 C44 105.64(17) . . ?
C48 C45 C46 107.47(18) . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C45 C47 H47A 109.5 . . ?
C45 C47 H47B 109.5 . . ?
C45 C47 H47C 109.5 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C45 C48 H48A 109.5 . . ?
C45 C48 H48B 109.5 . . ?
C45 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C25 N2 C44 115.30(16) . . ?
C29 N2 C25 110.30(16) . . ?
C29 N2 C44 108.69(15) . . ?
B2 O2 H2 109.5 . . ?
Cl1 C49 H49 108.5 . . ?
Cl1 C49 Cl2 110.04(12) . . ?
Cl1 C49 Cl3 111.10(13) . . ?
Cl2 C49 H49 108.5 . . ?
Cl3 C49 H49 108.5 . . ?
Cl3 C49 Cl2 110.08(13) . . ?
Cl4 C50 H50 108.1 . . ?
Cl5 C50 H50 108.1 . . ?
Cl5 C50 Cl4 110.13(13) . . ?
Cl5 C50 Cl6 112.10(14) . . ?
Cl6 C50 H50 108.1 . . ?
Cl6 C50 Cl4 110.23(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
B1 C18 C19 C10 -4.7(3) . . . . ?
B1 C18 C19 C14 175.82(18) . . . . ?
C1 C2 C3 C4 -31.6(3) . . . . ?
C2 C1 N1 C5 -58.3(2) . . . . ?
C2 C1 N1 C20 65.5(3) . . . . ?
C2 C3 C4 C5 5.2(3) . . . . ?
C2 C3 C4 C6 -177.61(19) . . . . ?
C3 C4 C5 C9 175.49(19) . . . . ?
C3 C4 C5 N1 -3.9(3) . . . . ?
C3 C4 C6 C7 -179.5(2) . . . . ?
C4 C5 C9 B1 -163.57(19) . . . . ?
C4 C5 C9 C8 5.3(3) . . . . ?
C4 C5 N1 C1 29.6(2) . . . . ?
C4 C5 N1 C20 -98.0(2) . . . . ?
C4 C6 C7 C8 2.3(3) . . . . ?
C5 C4 C6 C7 -2.1(3) . . . . ?
C6 C4 C5 C9 -1.8(3) . . . . ?
C6 C4 C5 N1 178.89(18) . . . . ?
C6 C7 C8 C9 1.3(3) . . . . ?
C6 C7 C8 C10 -179.52(19) . . . . ?
C7 C8 C9 B1 164.27(19) . . . . ?
C7 C8 C9 C5 -5.0(3) . . . . ?
C7 C8 C10 C11 13.3(3) . . . . ?
C7 C8 C10 C19 -167.71(19) . . . . ?
C8 C10 C11 C12 -179.07(19) . . . . ?
C8 C10 C19 C14 178.52(18) . . . . ?
C8 C10 C19 C18 -0.9(3) . . . . ?
C9 B1 C18 C17 178.82(19) . . . . ?
C9 B1 C18 C19 0.9(3) . . . . ?
C9 C5 N1 C1 -149.82(17) . . . . ?
C9 C5 N1 C20 82.6(2) . . . . ?
C9 C8 C10 C11 -167.60(19) . . . . ?
C9 C8 C10 C19 11.4(3) . . . . ?
C10 C8 C9 B1 -14.9(3) . . . . ?
C10 C8 C9 C5 175.87(17) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C10 C19 C14 -2.4(3) . . . . ?
C11 C10 C19 C18 178.12(19) . . . . ?
C11 C12 C13 C14 -1.6(3) . . . . ?
C12 C13 C14 C15 -179.8(2) . . . . ?
C12 C13 C14 C19 1.0(3) . . . . ?
C13 C14 C15 C16 -178.7(2) . . . . ?
C13 C14 C19 C10 1.1(3) . . . . ?
C13 C14 C19 C18 -179.50(19) . . . . ?
C14 C15 C16 C17 -1.3(4) . . . . ?
C15 C14 C19 C10 -178.2(2) . . . . ?
C15 C14 C19 C18 1.3(3) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C16 C17 C18 B1 -176.5(2) . . . . ?
C16 C17 C18 C19 1.4(3) . . . . ?
C17 C18 C19 C10 177.25(19) . . . . ?
C17 C18 C19 C14 -2.2(3) . . . . ?
C18 B1 C9 C5 177.92(18) . . . . ?
C18 B1 C9 C8 8.9(3) . . . . ?
C19 C10 C11 C12 1.9(3) . . . . ?
C19 C14 C15 C16 0.5(3) . . . . ?
C21 C20 N1 C1 60.2(3) . . . . ?
C21 C20 N1 C5 -175.43(18) . . . . ?
N1 C1 C2 C3 60.3(3) . . . . ?
N1 C5 C9 B1 15.8(3) . . . . ?
N1 C5 C9 C8 -175.31(16) . . . . ?
N1 C20 C21 C22 -85.2(2) . . . . ?
N1 C20 C21 C23 157.57(19) . . . . ?
N1 C20 C21 C24 39.6(3) . . . . ?
O1 B1 C9 C5 1.4(3) . . . . ?
O1 B1 C9 C8 -167.53(19) . . . . ?
O1 B1 C18 C17 -4.6(3) . . . . ?
O1 B1 C18 C19 177.48(19) . . . . ?
B2 C42 C43 C34 -5.1(3) . . . . ?
B2 C42 C43 C38 174.89(18) . . . . ?
C25 C26 C27 C28 -33.2(3) . . . . ?
C26 C25 N2 C29 -58.1(2) . . . . ?
C26 C25 N2 C44 65.5(2) . . . . ?
C26 C27 C28 C29 6.7(3) . . . . ?
C26 C27 C28 C30 -176.39(18) . . . . ?
C27 C28 C29 C33 174.99(19) . . . . ?
C27 C28 C29 N2 -3.9(3) . . . . ?
C27 C28 C30 C31 -178.92(19) . . . . ?
C28 C29 C33 B2 -162.84(19) . . . . ?
C28 C29 C33 C32 5.4(3) . . . . ?
C28 C29 N2 C25 28.8(2) . . . . ?
C28 C29 N2 C44 -98.5(2) . . . . ?
C28 C30 C31 C32 2.1(3) . . . . ?
C29 C28 C30 C31 -1.8(3) . . . . ?
C30 C28 C29 C33 -1.9(3) . . . . ?
C30 C28 C29 N2 179.13(17) . . . . ?
C30 C31 C32 C33 1.5(3) . . . . ?
C30 C31 C32 C34 -179.31(18) . . . . ?
C31 C32 C33 B2 163.61(18) . . . . ?
C31 C32 C33 C29 -5.1(3) . . . . ?
C31 C32 C34 C35 13.6(3) . . . . ?
C31 C32 C34 C43 -167.93(19) . . . . ?
C32 C34 C35 C36 -179.73(19) . . . . ?
C32 C34 C43 C38 179.79(18) . . . . ?
C32 C34 C43 C42 -0.2(3) . . . . ?
C33 B2 C42 C41 175.87(19) . . . . ?
C33 B2 C42 C43 0.4(3) . . . . ?
C33 C29 N2 C25 -150.22(17) . . . . ?
C33 C29 N2 C44 82.5(2) . . . . ?
C33 C32 C34 C35 -167.28(19) . . . . ?
C33 C32 C34 C43 11.2(3) . . . . ?
C34 C32 C33 B2 -15.6(3) . . . . ?
C34 C32 C33 C29 175.74(17) . . . . ?
C34 C35 C36 C37 -0.4(3) . . . . ?
C35 C34 C43 C38 -1.7(3) . . . . ?
C35 C34 C43 C42 178.32(19) . . . . ?
C35 C36 C37 C38 -1.0(3) . . . . ?
C36 C37 C38 C39 -178.4(2) . . . . ?
C36 C37 C38 C43 1.0(3) . . . . ?
C37 C38 C39 C40 -180.0(2) . . . . ?
C37 C38 C43 C34 0.4(3) . . . . ?
C37 C38 C43 C42 -179.63(19) . . . . ?
C38 C39 C40 C41 -0.1(3) . . . . ?
C39 C38 C43 C34 179.80(19) . . . . ?
C39 C38 C43 C42 -0.2(3) . . . . ?
C39 C40 C41 C42 -0.9(3) . . . . ?
C40 C41 C42 B2 -174.25(19) . . . . ?
C40 C41 C42 C43 1.3(3) . . . . ?
C41 C42 C43 C34 179.30(19) . . . . ?
C41 C42 C43 C38 -0.7(3) . . . . ?
C42 B2 C33 C29 178.28(18) . . . . ?
C42 B2 C33 C32 9.9(3) . . . . ?
C43 C34 C35 C36 1.7(3) . . . . ?
C43 C38 C39 C40 0.6(3) . . . . ?
C45 C44 N2 C25 62.2(2) . . . . ?
C45 C44 N2 C29 -173.45(17) . . . . ?
N2 C25 C26 C27 61.2(2) . . . . ?
N2 C29 C33 B2 16.1(3) . . . . ?
N2 C29 C33 C32 -175.61(17) . . . . ?
N2 C44 C45 C46 -86.9(2) . . . . ?
N2 C44 C45 C47 37.8(3) . . . . ?
N2 C44 C45 C48 156.07(18) . . . . ?
O2 B2 C33 C29 1.7(3) . . . . ?
O2 B2 C33 C32 -166.67(19) . . . . ?
O2 B2 C42 C41 -7.4(3) . . . . ?
O2 B2 C42 C43 177.06(18) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted in oil on MITEGEN holder.'
_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 1.144
_oxdiff_exptl_absorpt_empirical_full_min 0.927
_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 0.5659(6) 21450 49323 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.4341(6) 21469 49323 nmt -0.9996 0.0002 0.0009 -0.4879 0.9990 -0.0058
-0.0004 -0.0037 -0.9989

_twin_special_details            
;
Component 2 rotated by 179.9465° 
around [0.00 1.00 -0.00] (reciprocal) or [-0.24 0.97 -0.00] (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_mu667b_reprocess
_database_code_depnum_ccdc_archive 'CCDC 2221506'
loop_
_audit_author_name
_audit_author_address
'Gary Stephen Nichol'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-11-22 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;
_audit_creation_date             2022-11-22
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H25 B2 Br2 N O, C6 H6'
_chemical_formula_sum            'C30 H31 B2 Br2 N O'
_chemical_formula_weight         603.00
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.83580(10)
_cell_length_b                   11.60820(10)
_cell_length_c                   22.5888(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2579.10(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21042
_cell_measurement_temperature    119.99(17)
_cell_measurement_theta_max      29.4350
_cell_measurement_theta_min      3.6110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.168
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91579
_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    1.553
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 -3 28 0.1376
-1 2 32 0.1383
6 7 25 0.1531
10 8 -15 0.1045
-11 -2 -18 0.1333
-1 -14 16 0.1107
4 15 -10 0.1113
14 0 -7 0.0974
-9 5 21 0.1460
-5 -11 -21 0.1600
4 3 -30 0.1477

_exptl_crystal_recrystallization_method 
'Crystallised at room temperature by layering concentrated DCM solution with benzene.'
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.339
_exptl_crystal_size_min          0.261
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            57746
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.495
_diffrn_reflns_theta_min         3.510
_diffrn_ambient_temperature      120.00
_diffrn_detector_area_resol_mean 16.1042
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  15.00   1.00    5.00    --  -15.82 106.00  22.00   74
  2  ω    -15.00  60.00   1.00    5.00    --   17.54-106.00 -76.00   75
  3  ω    -88.00 -39.00   1.00    5.00    --  -15.82-178.00  90.00   49
  4  ω    -39.00  11.00   1.00    5.00    --  -15.82 -77.00   0.00   50
  5  ω    -33.00  51.00   1.00    5.00    --  -15.82  57.00 -30.00   84
  6  ω    -35.00  53.00   1.00    5.00    --  -15.82  38.00  90.00   88
  7  ω    -39.00  11.00   1.00    5.00    --  -15.82 -77.00 120.00   50
  8  ω     -9.00  39.00   1.00    5.00    --   17.54  77.00 120.00   48
  9  ω     39.00  90.00   1.00    5.00    --   17.54 178.00-120.00   51
 10  ω    -54.00  47.00   1.00    5.00    --   17.54 -19.00 150.00  101
 11  ω     -1.00  87.00   1.00    5.00    --   17.54  38.00   0.00   88
 12  ω    -83.00   1.00   1.00    5.00    --  -15.82 -57.00  60.00   84
 13  ω     -9.00  39.00   1.00    5.00    --   17.54  77.00 -60.00   48
 14  ω      1.00  48.00   1.00    5.00    --   17.54  57.00-150.00   47
 15  ω     -9.00  39.00   1.00    5.00    --   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_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.893
_reflns_number_gt                6143
_reflns_number_total             6623
_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. 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 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.494(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         6623
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0257
_refine_ls_restrained_S_all      1.051
_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)+(0.0253P)²+1.8106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0578
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.506(9)
 0.494(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1(H1A,H1B), C20(H20A,H20B), C3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C17(H17), C16(H16), C12(H12), C6(H6), C11(H11), C13(H13), C5(H5),
 C30(H30), C28(H28), C25(H25), C29(H29), C27(H27), C26(H26)
3.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.47600(3) 0.36725(3) 0.49496(2) 0.01518(7) Uani 1 1 d . . . . .
Br2 Br 0.27666(3) 0.29462(3) 0.38513(2) 0.01887(8) Uani 1 1 d . . . . .
O1 O 0.3496(2) 0.52349(19) 0.41350(9) 0.0132(4) Uani 1 1 d . . . . .
N1 N 0.5485(3) 0.4176(2) 0.36840(11) 0.0126(5) Uani 1 1 d . . . . .
C8 C 0.5805(3) 0.6144(3) 0.40642(13) 0.0122(6) Uani 1 1 d . . . . .
C18 C 0.3621(3) 0.7424(3) 0.42241(14) 0.0124(6) Uani 1 1 d . . . . .
C15 C 0.2531(3) 0.9619(3) 0.44363(14) 0.0181(7) Uani 1 1 d . . . . .
H15 H 0.215471 1.036047 0.450510 0.022 Uiso 1 1 calc R U . . .
C7 C 0.6616(3) 0.7100(3) 0.42088(13) 0.0139(6) Uani 1 1 d . . . . .
B2 B 0.4134(4) 0.4153(3) 0.41243(16) 0.0128(7) Uani 1 1 d . . . . .
C17 C 0.2229(4) 0.7614(3) 0.42214(14) 0.0159(6) Uani 1 1 d . . . . .
H17 H 0.163320 0.698418 0.415105 0.019 Uiso 1 1 calc R U . . .
C16 C 0.1679(3) 0.8710(3) 0.43197(14) 0.0187(6) Uani 1 1 d . . . . .
H16 H 0.072335 0.882418 0.430572 0.022 Uiso 1 1 calc R U . . .
C2 C 0.7433(3) 0.2855(3) 0.40061(15) 0.0196(7) Uani 1 1 d . . . . .
H2A H 0.783108 0.208356 0.393471 0.024 Uiso 1 1 calc R U . . .
H2B H 0.720250 0.291150 0.443171 0.024 Uiso 1 1 calc R U . . .
C9 C 0.6416(3) 0.5097(3) 0.39049(14) 0.0124(6) Uani 1 1 d . . . . .
C19 C 0.4520(3) 0.8365(3) 0.43376(13) 0.0131(6) Uani 1 1 d . . . . .
C12 C 0.6179(4) 1.0236(3) 0.46645(15) 0.0190(7) Uani 1 1 d . . . . .
H12 H 0.674817 1.085150 0.478835 0.023 Uiso 1 1 calc R U . . .
C6 C 0.8035(3) 0.6950(3) 0.42104(14) 0.0159(6) Uani 1 1 d . . . . .
H6 H 0.860920 0.758684 0.429480 0.019 Uiso 1 1 calc R U . . .
C1 C 0.6153(3) 0.2987(3) 0.36409(14) 0.0170(6) Uani 1 1 d . . . . .
H1A H 0.548806 0.239823 0.376958 0.020 Uiso 1 1 calc R U . . .
H1B H 0.637637 0.283209 0.322101 0.020 Uiso 1 1 calc R U . . .
C11 C 0.6751(4) 0.9159(3) 0.45305(15) 0.0177(7) Uani 1 1 d . . . . .
H11 H 0.770952 0.906984 0.455587 0.021 Uiso 1 1 calc R U . . .
C20 C 0.4925(3) 0.4494(3) 0.30619(12) 0.0141(6) Uani 1 1 d . . . . .
H20A H 0.446893 0.379444 0.290958 0.017 Uiso 1 1 calc R U . . .
H20B H 0.420069 0.507220 0.312808 0.017 Uiso 1 1 calc R U . . .
C13 C 0.4807(4) 1.0402(3) 0.46176(13) 0.0168(6) Uani 1 1 d . . . . .
H13 H 0.442771 1.113968 0.469329 0.020 Uiso 1 1 calc R U . . .
C10 C 0.5971(3) 0.8222(3) 0.43627(13) 0.0129(6) Uani 1 1 d . . . . .
C14 C 0.3954(3) 0.9472(3) 0.44559(14) 0.0154(6) Uani 1 1 d . . . . .
B1 B 0.4249(3) 0.6227(3) 0.41310(14) 0.0119(6) Uani 1 1 d . . . . .
C4 C 0.7821(3) 0.4931(3) 0.39365(13) 0.0143(6) Uani 1 1 d . . . . .
C3 C 0.8470(3) 0.3773(3) 0.38505(16) 0.0188(6) Uani 1 1 d . . . . .
H3A H 0.927820 0.369941 0.410886 0.023 Uiso 1 1 calc R U . . .
H3B H 0.876475 0.368268 0.343410 0.023 Uiso 1 1 calc R U . . .
C5 C 0.8599(3) 0.5891(3) 0.40911(15) 0.0183(7) Uani 1 1 d . . . . .
H5 H 0.955880 0.580974 0.411487 0.022 Uiso 1 1 calc R U . . .
C23 C 0.4761(4) 0.5041(3) 0.20371(14) 0.0258(8) Uani 1 1 d . . . . .
H23A H 0.441336 0.427103 0.194502 0.039 Uiso 1 1 calc R U . . .
H23B H 0.520529 0.536478 0.168600 0.039 Uiso 1 1 calc R U . . .
H23C H 0.400619 0.554093 0.215623 0.039 Uiso 1 1 calc R U . . .
C30 C 0.1153(4) 0.5304(4) 0.28739(17) 0.0312(9) Uani 1 1 d . . . . .
H30 H 0.144571 0.521989 0.327235 0.037 Uiso 1 1 calc R U . . .
C24 C 0.6345(4) 0.6185(3) 0.26530(16) 0.0286(8) Uani 1 1 d . . . . .
H24A H 0.560865 0.667438 0.280177 0.043 Uiso 1 1 calc R U . . .
H24B H 0.668817 0.649992 0.227934 0.043 Uiso 1 1 calc R U . . .
H24C H 0.708271 0.616077 0.294420 0.043 Uiso 1 1 calc R U . . .
C21 C 0.5803(4) 0.4959(3) 0.25488(14) 0.0207(7) Uani 1 1 d . . . . .
C28 C 0.0140(4) 0.6458(4) 0.21113(18) 0.0353(9) Uani 1 1 d . . . . .
H28 H -0.026691 0.715905 0.198555 0.042 Uiso 1 1 calc R U . . .
C25 C 0.1301(4) 0.4417(4) 0.24847(19) 0.0344(9) Uani 1 1 d . . . . .
H25 H 0.169733 0.371341 0.261176 0.041 Uiso 1 1 calc R U . . .
C29 C 0.0572(4) 0.6339(4) 0.26854(18) 0.0355(9) Uani 1 1 d . . . . .
H29 H 0.047522 0.696093 0.295538 0.043 Uiso 1 1 calc R U . . .
C27 C 0.0295(5) 0.5561(4) 0.17166(17) 0.0395(11) Uani 1 1 d . . . . .
H27 H 0.000469 0.564827 0.131790 0.047 Uiso 1 1 calc R U . . .
C26 C 0.0870(5) 0.4540(4) 0.18998(19) 0.0387(10) Uani 1 1 d . . . . .
H26 H 0.097279 0.392088 0.162856 0.046 Uiso 1 1 calc R U . . .
C22 C 0.6962(4) 0.4188(4) 0.23469(16) 0.0321(9) Uani 1 1 d . . . . .
H22A H 0.767256 0.417537 0.265119 0.048 Uiso 1 1 calc R U . . .
H22B H 0.734149 0.448714 0.197630 0.048 Uiso 1 1 calc R U . . .
H22C H 0.662103 0.340480 0.228313 0.048 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 B2 2.041(4) . ?
Br2 B2 2.038(4) . ?
O1 B2 1.404(4) . ?
O1 B1 1.369(4) . ?
N1 B2 1.660(4) . ?
N1 C9 1.494(4) . ?
N1 C1 1.532(4) . ?
N1 C20 1.554(4) . ?
C8 C7 1.405(4) . ?
C8 C9 1.402(4) . ?
C8 B1 1.541(5) . ?
C18 C17 1.387(5) . ?
C18 C19 1.428(4) . ?
C18 B1 1.536(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.372(5) . ?
C15 C14 1.411(5) . ?
C7 C6 1.406(4) . ?
C7 C10 1.490(5) . ?
C17 H17 0.9500 . ?
C17 C16 1.401(5) . ?
C16 H16 0.9500 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.513(4) . ?
C2 C3 1.517(4) . ?
C9 C4 1.397(4) . ?
C19 C10 1.437(4) . ?
C19 C14 1.426(4) . ?
C12 H12 0.9500 . ?
C12 C11 1.404(5) . ?
C12 C13 1.367(5) . ?
C6 H6 0.9500 . ?
C6 C5 1.375(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C11 H11 0.9500 . ?
C11 C10 1.384(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.542(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.415(5) . ?
C4 C3 1.501(4) . ?
C4 C5 1.396(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C23 C21 1.547(5) . ?
C30 H30 0.9500 . ?
C30 C25 1.362(6) . ?
C30 C29 1.396(6) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C24 C21 1.537(5) . ?
C21 C22 1.520(5) . ?
C28 H28 0.9500 . ?
C28 C29 1.372(6) . ?
C28 C27 1.379(6) . ?
C25 H25 0.9500 . ?
C25 C26 1.395(6) . ?
C29 H29 0.9500 . ?
C27 H27 0.9500 . ?
C27 C26 1.377(7) . ?
C26 H26 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
B1 O1 B2 120.6(3) . . ?
C9 N1 B2 107.6(2) . . ?
C9 N1 C1 113.8(2) . . ?
C9 N1 C20 110.4(2) . . ?
C1 N1 B2 111.5(2) . . ?
C1 N1 C20 108.0(2) . . ?
C20 N1 B2 105.2(2) . . ?
C7 C8 B1 119.4(3) . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 B1 120.3(3) . . ?
C17 C18 C19 119.4(3) . . ?
C17 C18 B1 122.7(3) . . ?
C19 C18 B1 117.8(3) . . ?
C16 C15 H15 119.4 . . ?
C16 C15 C14 121.2(3) . . ?
C14 C15 H15 119.4 . . ?
C8 C7 C6 117.7(3) . . ?
C8 C7 C10 120.2(3) . . ?
C6 C7 C10 122.0(3) . . ?
Br2 B2 Br1 106.70(16) . . ?
O1 B2 Br1 111.3(2) . . ?
O1 B2 Br2 109.0(2) . . ?
O1 B2 N1 110.7(2) . . ?
N1 B2 Br1 108.1(2) . . ?
N1 B2 Br2 111.0(2) . . ?
C18 C17 H17 119.2 . . ?
C18 C17 C16 121.6(3) . . ?
C16 C17 H17 119.2 . . ?
C15 C16 C17 119.6(3) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
H2A C2 H2B 108.0 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C1 C2 C3 111.2(3) . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C8 C9 N1 116.3(3) . . ?
C4 C9 N1 121.7(3) . . ?
C4 C9 C8 122.0(3) . . ?
C18 C19 C10 122.3(3) . . ?
C14 C19 C18 118.7(3) . . ?
C14 C19 C10 118.9(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C13 C12 C11 120.3(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 C7 120.7(3) . . ?
C5 C6 H6 119.6 . . ?
N1 C1 H1A 108.6 . . ?
N1 C1 H1B 108.6 . . ?
C2 C1 N1 114.5(3) . . ?
C2 C1 H1A 108.6 . . ?
C2 C1 H1B 108.6 . . ?
H1A C1 H1B 107.6 . . ?
C12 C11 H11 118.8 . . ?
C10 C11 C12 122.4(3) . . ?
C10 C11 H11 118.8 . . ?
N1 C20 H20A 106.2 . . ?
N1 C20 H20B 106.2 . . ?
H20A C20 H20B 106.4 . . ?
C21 C20 N1 124.4(3) . . ?
C21 C20 H20A 106.2 . . ?
C21 C20 H20B 106.2 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C19 C10 C7 120.9(3) . . ?
C11 C10 C7 121.0(3) . . ?
C11 C10 C19 118.1(3) . . ?
C15 C14 C19 119.4(3) . . ?
C15 C14 C13 120.3(3) . . ?
C13 C14 C19 120.3(3) . . ?
O1 B1 C8 119.1(3) . . ?
O1 B1 C18 122.8(3) . . ?
C18 B1 C8 118.0(3) . . ?
C9 C4 C3 122.5(3) . . ?
C5 C4 C9 116.4(3) . . ?
C5 C4 C3 120.9(3) . . ?
C2 C3 H3A 110.0 . . ?
C2 C3 H3B 110.0 . . ?
C4 C3 C2 108.3(3) . . ?
C4 C3 H3A 110.0 . . ?
C4 C3 H3B 110.0 . . ?
H3A C3 H3B 108.4 . . ?
C6 C5 C4 122.7(3) . . ?
C6 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
C25 C30 H30 120.1 . . ?
C25 C30 C29 119.8(4) . . ?
C29 C30 H30 120.1 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
C20 C21 C23 102.3(3) . . ?
C24 C21 C20 113.7(3) . . ?
C24 C21 C23 106.6(3) . . ?
C22 C21 C20 116.1(3) . . ?
C22 C21 C23 108.0(3) . . ?
C22 C21 C24 109.3(3) . . ?
C29 C28 H28 120.0 . . ?
C29 C28 C27 120.0(4) . . ?
C27 C28 H28 120.0 . . ?
C30 C25 H25 119.9 . . ?
C30 C25 C26 120.1(4) . . ?
C26 C25 H25 119.9 . . ?
C30 C29 H29 119.9 . . ?
C28 C29 C30 120.1(4) . . ?
C28 C29 H29 119.9 . . ?
C28 C27 H27 120.0 . . ?
C26 C27 C28 120.1(4) . . ?
C26 C27 H27 120.0 . . ?
C25 C26 H26 120.1 . . ?
C27 C26 C25 119.8(4) . . ?
C27 C26 H26 120.1 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 C9 C4 C3 -10.4(5) . . . . ?
N1 C9 C4 C5 173.5(3) . . . . ?
N1 C20 C21 C23 176.2(3) . . . . ?
N1 C20 C21 C24 -69.2(4) . . . . ?
N1 C20 C21 C22 58.9(4) . . . . ?
C8 C7 C6 C5 -1.9(5) . . . . ?
C8 C7 C10 C19 -3.2(5) . . . . ?
C8 C7 C10 C11 177.2(3) . . . . ?
C8 C9 C4 C3 171.2(3) . . . . ?
C8 C9 C4 C5 -4.9(5) . . . . ?
C18 C17 C16 C15 -1.6(5) . . . . ?
C18 C19 C10 C7 6.4(5) . . . . ?
C18 C19 C10 C11 -174.0(3) . . . . ?
C18 C19 C14 C15 -2.3(4) . . . . ?
C18 C19 C14 C13 174.8(3) . . . . ?
C7 C8 C9 N1 -172.4(3) . . . . ?
C7 C8 C9 C4 6.1(5) . . . . ?
C7 C8 B1 O1 -163.8(3) . . . . ?
C7 C8 B1 C18 12.9(4) . . . . ?
C7 C6 C5 C4 3.1(5) . . . . ?
B2 O1 B1 C8 4.8(4) . . . . ?
B2 O1 B1 C18 -171.7(3) . . . . ?
B2 N1 C9 C8 -43.8(3) . . . . ?
B2 N1 C9 C4 137.7(3) . . . . ?
B2 N1 C1 C2 -102.7(3) . . . . ?
B2 N1 C20 C21 161.6(3) . . . . ?
C17 C18 C19 C10 178.3(3) . . . . ?
C17 C18 C19 C14 1.1(4) . . . . ?
C17 C18 B1 O1 -11.0(5) . . . . ?
C17 C18 B1 C8 172.4(3) . . . . ?
C16 C15 C14 C19 1.6(5) . . . . ?
C16 C15 C14 C13 -175.6(3) . . . . ?
C9 N1 B2 Br1 -64.6(2) . . . . ?
C9 N1 B2 Br2 178.67(19) . . . . ?
C9 N1 B2 O1 57.5(3) . . . . ?
C9 N1 C1 C2 19.3(4) . . . . ?
C9 N1 C20 C21 45.8(4) . . . . ?
C9 C8 C7 C6 -2.5(4) . . . . ?
C9 C8 C7 C10 178.4(3) . . . . ?
C9 C8 B1 O1 11.3(4) . . . . ?
C9 C8 B1 C18 -172.0(3) . . . . ?
C9 C4 C3 C2 -25.1(4) . . . . ?
C9 C4 C5 C6 0.3(5) . . . . ?
C19 C18 C17 C16 0.8(5) . . . . ?
C19 C18 B1 O1 166.9(3) . . . . ?
C19 C18 B1 C8 -9.8(4) . . . . ?
C12 C11 C10 C7 178.4(3) . . . . ?
C12 C11 C10 C19 -1.2(5) . . . . ?
C12 C13 C14 C15 176.7(3) . . . . ?
C12 C13 C14 C19 -0.5(5) . . . . ?
C6 C7 C10 C19 177.8(3) . . . . ?
C6 C7 C10 C11 -1.8(5) . . . . ?
C1 N1 B2 Br1 60.8(3) . . . . ?
C1 N1 B2 Br2 -55.9(3) . . . . ?
C1 N1 B2 O1 -177.0(2) . . . . ?
C1 N1 C9 C8 -167.9(3) . . . . ?
C1 N1 C9 C4 13.6(4) . . . . ?
C1 N1 C20 C21 -79.2(3) . . . . ?
C1 C2 C3 C4 56.6(4) . . . . ?
C11 C12 C13 C14 2.5(5) . . . . ?
C20 N1 B2 Br1 177.62(19) . . . . ?
C20 N1 B2 Br2 60.9(3) . . . . ?
C20 N1 B2 O1 -60.2(3) . . . . ?
C20 N1 C9 C8 70.5(3) . . . . ?
C20 N1 C9 C4 -108.0(3) . . . . ?
C20 N1 C1 C2 142.2(3) . . . . ?
C13 C12 C11 C10 -1.7(5) . . . . ?
C10 C7 C6 C5 177.2(3) . . . . ?
C10 C19 C14 C15 -179.6(3) . . . . ?
C10 C19 C14 C13 -2.4(5) . . . . ?
C14 C15 C16 C17 0.4(5) . . . . ?
C14 C19 C10 C7 -176.4(3) . . . . ?
C14 C19 C10 C11 3.2(5) . . . . ?
B1 O1 B2 Br1 81.9(3) . . . . ?
B1 O1 B2 Br2 -160.7(2) . . . . ?
B1 O1 B2 N1 -38.3(4) . . . . ?
B1 C8 C7 C6 172.5(3) . . . . ?
B1 C8 C7 C10 -6.5(4) . . . . ?
B1 C8 C9 N1 12.6(4) . . . . ?
B1 C8 C9 C4 -169.0(3) . . . . ?
B1 C18 C17 C16 178.6(3) . . . . ?
B1 C18 C19 C10 0.4(5) . . . . ?
B1 C18 C19 C14 -176.8(3) . . . . ?
C3 C2 C1 N1 -55.6(4) . . . . ?
C3 C4 C5 C6 -175.8(3) . . . . ?
C5 C4 C3 C2 150.7(3) . . . . ?
C30 C25 C26 C27 0.0(7) . . . . ?
C28 C27 C26 C25 -0.3(7) . . . . ?
C25 C30 C29 C28 0.5(6) . . . . ?
C29 C30 C25 C26 -0.1(6) . . . . ?
C29 C28 C27 C26 0.7(7) . . . . ?
C27 C28 C29 C30 -0.8(6) . . . . ?

_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
;
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.506(9)
2 0.494(9)

