# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_sx_nsa195_twin1_hklf4
_audit_block_doi                 10.5517/ccdc.csd.cc2p3khw
_database_code_depnum_ccdc_archive 'CCDC 2476078'
loop_
_audit_author_name
_audit_author_address
'Nattamai Bhuvanesh'
;Texas A and M university Crystallographic center
United States of America
;
_audit_update_record             
;
2025-07-25 deposited with the CCDC.	2025-12-29 downloaded from the CCDC.
;
_audit_creation_date             2025-04-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
shiqing.xu@tamu.edu
nbhuv@mail.chem.tamu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H31 B N2 O3, H2 O'
_chemical_formula_sum            'C23 H33 B N2 O4'
_chemical_formula_weight         412.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         C23H31N2BO3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.2002(3)
_cell_length_b                   14.5736(8)
_cell_length_c                   21.7237(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.027(4)
_cell_angle_gamma                90
_cell_volume                     2262.41(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6512
_cell_measurement_temperature    99.9(4)
_cell_measurement_theta_max      77.6290
_cell_measurement_theta_min      3.5540
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.745
_exptl_absorpt_coefficient_mu    0.653
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
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    1.211
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.024
_exptl_crystal_size_min          0.013
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            5286
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.479
_diffrn_reflns_theta_min         3.661
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -62.00   0.50    8.96    --  -47.48-142.00  72.00  116
  2  ω   -118.00 -71.00   0.50    8.96    --  -47.48-129.00-116.00   94
  3  ω    -89.00 -15.00   0.50    8.96    --  -47.48 129.00 -42.00  148
  4  ω     44.00 105.00   0.50    8.96    --   47.48-142.00  72.00  122
  5  ω     37.00  96.00   0.50    8.96    --   47.48-129.00-116.00  118
  6  ω   -155.00 -62.00   0.50   35.85    --  -91.75-142.00  72.00  186
  7  ω    -88.00 -21.00   0.50   35.85    --  -91.75 129.00 -42.00  134
  8  ω     79.00 113.00   0.50   35.85    --  113.25-129.00-116.00   68
  9  ω    104.00 133.00   0.50   35.85    --  113.25 129.00 -42.00   58
 10  ω     92.00 124.00   0.50   35.85    --  113.25-142.00  72.00   64
 11  ω     47.00  86.00   0.50   35.85    --  113.25-142.00  72.00   78
 12  ω    -12.00  27.00   0.50    8.96    --  -47.48  19.00  60.00   78
 13  ω    -12.00  28.00   0.50    8.96    --  -47.48  19.00 150.00   80
 14  ω    -27.00  10.00   0.50    8.96    --   47.48 -19.00-180.00   74
 15  ω   -158.00-108.00   0.50   35.85    --  -91.75 -61.00   0.00  100
 16  ω    -46.00 -21.00   0.50   35.85    --  -91.75  45.00 120.00   50
 17  ω    -49.00 -20.00   0.50   35.85    --  -91.75  45.00-180.00   58
 18  ω     42.00 106.00   0.50   35.85    --  113.25 -95.00  90.00  128
 19  ω    101.00 173.00   0.50   35.85    --  113.25  15.00  90.00  144
 20  ω     42.00  74.00   0.50   35.85    --  113.25 -61.00 150.00   64
 21  ω     42.00  74.00   0.50   35.85    --  113.25 -61.00 -60.00   64
 22  ω    147.00 178.00   0.50   35.85    --  113.25  30.00  60.00   62
 23  ω    101.00 126.00   0.50   35.85    --  113.25  30.00  60.00   50
 24  ω     42.00 136.00   0.50   35.85    --  113.25 -77.00-120.00  188
 25  ω    104.00 129.00   0.50   35.85    --  113.25 142.00 128.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0004475000
_diffrn_orient_matrix_UB_12      0.0192461000
_diffrn_orient_matrix_UB_13      0.0697668000
_diffrn_orient_matrix_UB_21      -0.0104024000
_diffrn_orient_matrix_UB_22      -0.1037952000
_diffrn_orient_matrix_UB_23      0.0124990000
_diffrn_orient_matrix_UB_31      0.2152269000
_diffrn_orient_matrix_UB_32      -0.0049604000
_diffrn_orient_matrix_UB_33      0.0089353000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           '1 mA'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           '50 kV'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4694
_reflns_number_total             5286
_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 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.142a 64-bit (release 17-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         5286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0631P)²+0.9677P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1221
_refine_special_details          
;
Several crystals were tried and found all of them 
to be twinned. The best among them was used for 
data collection. Data integration was carried out 
including both the twin components. Reflections 
from only the major component was used for final 
least square refinement cycles. 
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7537(13)
 0.2463(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
3.a Free rotating group:
 O4(H4D,H4E)
3.b Ternary CH refined with riding coordinates:
 C8(H8)
3.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C17(H17A,H17B)
3.d Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C19(H19), C20(H20),
 C21(H21), C22(H22), C23(H23)
3.e X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
3.f Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.69738(18) 0.37853(8) 0.45750(5) 0.0250(3) Uani 1 1 d . . . . .
O2 O 0.83949(18) 0.22677(9) 0.46841(6) 0.0261(3) Uani 1 1 d . . . . .
O3 O 0.51603(17) 0.23402(8) 0.45364(5) 0.0228(3) Uani 1 1 d . . . . .
N1 N 0.7103(2) 0.40460(10) 0.55879(6) 0.0221(3) Uani 1 1 d . . . . .
N2 N 0.7482(2) 0.52493(10) 0.48881(7) 0.0268(3) Uani 1 1 d . . . . .
H2A H 0.750973 0.541835 0.450044 0.032 Uiso 1 1 calc R U . . .
H2B H 0.763950 0.565969 0.518706 0.032 Uiso 1 1 calc R U . . .
C1 C 0.7720(3) 0.14689(13) 0.43344(9) 0.0258(4) Uani 1 1 d . . . . .
C2 C 0.5741(3) 0.17758(13) 0.40463(8) 0.0244(4) Uani 1 1 d . . . . .
C3 C 0.7645(3) 0.06682(13) 0.47860(9) 0.0306(4) Uani 1 1 d . . . . .
H3A H 0.887495 0.058932 0.502829 0.046 Uiso 1 1 calc R U . . .
H3B H 0.730257 0.010520 0.455261 0.046 Uiso 1 1 calc R U . . .
H3C H 0.670949 0.079705 0.506634 0.046 Uiso 1 1 calc R U . . .
C4 C 0.9055(3) 0.12316(16) 0.38653(10) 0.0352(5) Uani 1 1 d . . . . .
H4A H 0.926200 0.177643 0.361824 0.053 Uiso 1 1 calc R U . . .
H4B H 0.850964 0.074216 0.359116 0.053 Uiso 1 1 calc R U . . .
H4C H 1.025077 0.102368 0.408481 0.053 Uiso 1 1 calc R U . . .
C5 C 0.4353(3) 0.10009(14) 0.39062(9) 0.0301(4) Uani 1 1 d . . . . .
H5A H 0.411383 0.070783 0.429481 0.045 Uiso 1 1 calc R U . . .
H5B H 0.486853 0.054751 0.364022 0.045 Uiso 1 1 calc R U . . .
H5C H 0.317953 0.124557 0.369293 0.045 Uiso 1 1 calc R U . . .
C6 C 0.5793(3) 0.23739(14) 0.34683(9) 0.0335(4) Uani 1 1 d . . . . .
H6A H 0.458310 0.268079 0.336699 0.050 Uiso 1 1 calc R U . . .
H6B H 0.604702 0.198760 0.311888 0.050 Uiso 1 1 calc R U . . .
H6C H 0.678197 0.283569 0.354935 0.050 Uiso 1 1 calc R U . . .
C7 C 0.7202(2) 0.43770(12) 0.50216(8) 0.0223(3) Uani 1 1 d . . . . .
C8 C 0.6785(3) 0.30422(12) 0.55826(8) 0.0229(4) Uani 1 1 d . . . . .
H8 H 0.789065 0.274260 0.582546 0.027 Uiso 1 1 calc R U . . .
C9 C 0.5035(3) 0.28007(12) 0.58877(8) 0.0255(4) Uani 1 1 d . . . . .
H9A H 0.515104 0.306938 0.630917 0.031 Uiso 1 1 calc R U . . .
H9B H 0.392348 0.307660 0.564321 0.031 Uiso 1 1 calc R U . . .
C10 C 0.4745(3) 0.17638(14) 0.59330(10) 0.0317(4) Uani 1 1 d . . . . .
H10A H 0.432807 0.151926 0.551362 0.038 Uiso 1 1 calc R U . . .
H10B H 0.595636 0.147137 0.608374 0.038 Uiso 1 1 calc R U . . .
C11 C 0.3329(3) 0.15067(12) 0.63595(9) 0.0260(4) Uani 1 1 d . . . . .
C12 C 0.3886(3) 0.12679(15) 0.69748(10) 0.0356(5) Uani 1 1 d . . . . .
H12 H 0.517727 0.127584 0.713115 0.043 Uiso 1 1 calc R U . . .
C13 C 0.2577(4) 0.10184(16) 0.73621(10) 0.0409(5) Uani 1 1 d . . . . .
H13 H 0.297603 0.086163 0.778188 0.049 Uiso 1 1 calc R U . . .
C14 C 0.0702(3) 0.09964(15) 0.71420(10) 0.0397(5) Uani 1 1 d . . . . .
H14 H -0.019339 0.081947 0.740631 0.048 Uiso 1 1 calc R U . . .
C15 C 0.0136(3) 0.12351(15) 0.65309(11) 0.0378(5) Uani 1 1 d . . . . .
H15 H -0.115536 0.122136 0.637452 0.045 Uiso 1 1 calc R U . . .
C16 C 0.1445(3) 0.14942(13) 0.61463(9) 0.0293(4) Uani 1 1 d . . . . .
H16 H 0.103866 0.166555 0.572966 0.035 Uiso 1 1 calc R U . . .
C17 C 0.7381(3) 0.45989(12) 0.61566(8) 0.0244(4) Uani 1 1 d . . . . .
H17A H 0.643094 0.442329 0.642825 0.029 Uiso 1 1 calc R U . . .
H17B H 0.718844 0.525434 0.604712 0.029 Uiso 1 1 calc R U . . .
C18 C 0.9308(3) 0.44782(12) 0.65087(8) 0.0241(4) Uani 1 1 d . . . . .
C19 C 1.0725(3) 0.51037(13) 0.64340(8) 0.0248(4) Uani 1 1 d . . . . .
H19 H 1.046920 0.561347 0.616439 0.030 Uiso 1 1 calc R U . . .
C20 C 1.2507(3) 0.49915(14) 0.67488(8) 0.0292(4) Uani 1 1 d . . . . .
H20 H 1.346492 0.542132 0.669375 0.035 Uiso 1 1 calc R U . . .
C21 C 1.2884(3) 0.42506(15) 0.71434(9) 0.0318(4) Uani 1 1 d . . . . .
H21 H 1.410234 0.417060 0.735915 0.038 Uiso 1 1 calc R U . . .
C22 C 1.1481(3) 0.36256(15) 0.72233(9) 0.0359(5) Uani 1 1 d . . . . .
H22 H 1.174173 0.311719 0.749385 0.043 Uiso 1 1 calc R U . . .
C23 C 0.9705(3) 0.37397(14) 0.69106(9) 0.0314(4) Uani 1 1 d . . . . .
H23 H 0.874815 0.331151 0.697032 0.038 Uiso 1 1 calc R U . . .
B1 B 0.6800(3) 0.27854(13) 0.48433(9) 0.0219(4) Uani 1 1 d . . . . .
O4 O 0.83301(19) 0.68150(9) 0.55983(6) 0.0298(3) Uani 1 1 d G . . . .
H4D H 0.924282 0.716410 0.551137 0.045 Uiso 1 1 d G U . . .
H4E H 0.734592 0.716540 0.554239 0.045 Uiso 1 1 d G 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
O1 C7 1.293(2) . ?
O1 B1 1.580(2) . ?
O2 C1 1.442(2) . ?
O2 B1 1.451(2) . ?
O3 C2 1.447(2) . ?
O3 B1 1.437(2) . ?
N1 C7 1.332(2) . ?
N1 C8 1.481(2) . ?
N1 C17 1.468(2) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C7 1.325(2) . ?
C1 C2 1.551(3) . ?
C1 C3 1.530(3) . ?
C1 C4 1.523(3) . ?
C2 C5 1.514(3) . ?
C2 C6 1.533(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 H8 1.0000 . ?
C8 C9 1.535(3) . ?
C8 B1 1.650(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.530(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.507(3) . ?
C11 C12 1.392(3) . ?
C11 C16 1.378(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.376(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(3) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.510(3) . ?
C18 C19 1.393(3) . ?
C18 C23 1.393(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.385(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.383(3) . ?
C23 H23 0.9500 . ?
O4 H4D 0.8699 . ?
O4 H4E 0.8699 . ?

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
C7 O1 B1 110.29(13) . . ?
C1 O2 B1 108.67(14) . . ?
B1 O3 C2 107.65(13) . . ?
C7 N1 C8 112.12(14) . . ?
C7 N1 C17 124.16(15) . . ?
C17 N1 C8 123.63(14) . . ?
H2A N2 H2B 120.0 . . ?
C7 N2 H2A 120.0 . . ?
C7 N2 H2B 120.0 . . ?
O2 C1 C2 102.33(14) . . ?
O2 C1 C3 108.32(15) . . ?
O2 C1 C4 109.66(15) . . ?
C3 C1 C2 112.09(16) . . ?
C4 C1 C2 114.78(16) . . ?
C4 C1 C3 109.30(16) . . ?
O3 C2 C1 101.59(13) . . ?
O3 C2 C5 109.20(15) . . ?
O3 C2 C6 108.52(15) . . ?
C5 C2 C1 114.66(16) . . ?
C5 C2 C6 109.95(15) . . ?
C6 C2 C1 112.42(16) . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 N1 115.79(16) . . ?
O1 C7 N2 118.98(16) . . ?
N2 C7 N1 125.22(16) . . ?
N1 C8 H8 108.4 . . ?
N1 C8 C9 110.96(14) . . ?
N1 C8 B1 102.25(13) . . ?
C9 C8 H8 108.4 . . ?
C9 C8 B1 118.14(15) . . ?
B1 C8 H8 108.4 . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 C8 112.34(15) . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C9 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 C9 113.15(16) . . ?
C11 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C12 C11 C10 121.03(18) . . ?
C16 C11 C10 120.57(17) . . ?
C16 C11 C12 118.39(19) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.41(19) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.4 . . ?
C13 C14 C15 119.3(2) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.3(2) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 120.98(18) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
N1 C17 H17A 109.1 . . ?
N1 C17 H17B 109.1 . . ?
N1 C17 C18 112.60(15) . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C19 C18 C17 120.38(16) . . ?
C19 C18 C23 118.78(18) . . ?
C23 C18 C17 120.84(17) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.80(17) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.75(19) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 119.96(19) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.23(19) . . ?
C23 C22 H22 119.9 . . ?
C18 C23 H23 119.8 . . ?
C22 C23 C18 120.48(19) . . ?
C22 C23 H23 119.8 . . ?
O1 B1 C8 99.22(13) . . ?
O2 B1 O1 106.90(14) . . ?
O2 B1 C8 116.71(15) . . ?
O3 B1 O1 110.05(14) . . ?
O3 B1 O2 106.48(14) . . ?
O3 B1 C8 116.82(15) . . ?
H4D O4 H4E 104.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2B O4 0.88 1.94 2.780(2) 158.7 . yes
O4 H4D O2 0.87 1.98 2.8421(19) 168.8 3_766 yes
O4 H4E O3 0.87 1.93 2.7817(18) 165.4 3_666 yes

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
O2 C1 C2 O3 -35.34(16) . . . . ?
O2 C1 C2 C5 -152.97(15) . . . . ?
O2 C1 C2 C6 80.47(17) . . . . ?
N1 C8 C9 C10 -175.81(15) . . . . ?
N1 C8 B1 O1 -4.60(16) . . . . ?
N1 C8 B1 O2 109.68(16) . . . . ?
N1 C8 B1 O3 -122.72(16) . . . . ?
N1 C17 C18 C19 96.73(19) . . . . ?
N1 C17 C18 C23 -83.0(2) . . . . ?
C1 O2 B1 O1 -123.04(14) . . . . ?
C1 O2 B1 O3 -5.42(18) . . . . ?
C1 O2 B1 C8 127.07(16) . . . . ?
C2 O3 B1 O1 96.78(16) . . . . ?
C2 O3 B1 O2 -18.73(18) . . . . ?
C2 O3 B1 C8 -151.16(15) . . . . ?
C3 C1 C2 O3 80.50(17) . . . . ?
C3 C1 C2 C5 -37.1(2) . . . . ?
C3 C1 C2 C6 -163.69(15) . . . . ?
C4 C1 C2 O3 -154.04(16) . . . . ?
C4 C1 C2 C5 88.3(2) . . . . ?
C4 C1 C2 C6 -38.2(2) . . . . ?
C7 O1 B1 O2 -115.97(15) . . . . ?
C7 O1 B1 O3 128.79(16) . . . . ?
C7 O1 B1 C8 5.71(18) . . . . ?
C7 N1 C8 C9 -124.27(16) . . . . ?
C7 N1 C8 B1 2.59(19) . . . . ?
C7 N1 C17 C18 -100.9(2) . . . . ?
C8 N1 C7 O1 1.3(2) . . . . ?
C8 N1 C7 N2 -179.83(17) . . . . ?
C8 N1 C17 C18 75.5(2) . . . . ?
C8 C9 C10 C11 166.34(16) . . . . ?
C9 C8 B1 O1 117.48(15) . . . . ?
C9 C8 B1 O2 -128.23(17) . . . . ?
C9 C8 B1 O3 -0.6(2) . . . . ?
C9 C10 C11 C12 -95.9(2) . . . . ?
C9 C10 C11 C16 84.8(2) . . . . ?
C10 C11 C12 C13 -179.0(2) . . . . ?
C10 C11 C16 C15 178.29(18) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C12 C11 C16 C15 -1.1(3) . . . . ?
C12 C13 C14 C15 -0.6(4) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C15 C16 C11 1.0(3) . . . . ?
C16 C11 C12 C13 0.4(3) . . . . ?
C17 N1 C7 O1 178.04(16) . . . . ?
C17 N1 C7 N2 -3.1(3) . . . . ?
C17 N1 C8 C9 58.9(2) . . . . ?
C17 N1 C8 B1 -174.19(15) . . . . ?
C17 C18 C19 C20 -179.08(16) . . . . ?
C17 C18 C23 C22 178.91(17) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C19 C18 C23 C22 -0.8(3) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C20 C21 C22 C23 -0.1(3) . . . . ?
C21 C22 C23 C18 0.5(3) . . . . ?
C23 C18 C19 C20 0.6(3) . . . . ?
B1 O1 C7 N1 -4.8(2) . . . . ?
B1 O1 C7 N2 176.23(16) . . . . ?
B1 O2 C1 C2 25.23(18) . . . . ?
B1 O2 C1 C3 -93.31(17) . . . . ?
B1 O2 C1 C4 147.48(16) . . . . ?
B1 O3 C2 C1 33.34(17) . . . . ?
B1 O3 C2 C5 154.84(15) . . . . ?
B1 O3 C2 C6 -85.30(17) . . . . ?
B1 C8 C9 C10 66.6(2) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder'
_olex2_submission_original_sample_id SXB_SN_250402_Sc_A195
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.637
_oxdiff_exptl_absorpt_empirical_full_min 0.459
_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 0.7537(13) 6688 11604 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.2463(13) 0 11604 nmt 0.9999 -0.0000 -0.0000 0.0002 -0.9998 0.0000 -0.7248
-0.0001 -1.0003

_twin_special_details            
;
Component 2 rotated by -179.9752° 
around [0.94 0.00 -0.34] (reciprocal) or [1.00 0.00 -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_xi_2025_5_13_ns
_audit_block_doi                 10.5517/ccdc.csd.cc2p3lr5
_database_code_depnum_ccdc_archive 'CCDC 2476117'
loop_
_audit_author_name
_audit_author_address
'Veerabhadra reddy Vulupala'
;Texas A and M university
United States of America
;
_audit_update_record             
;
2025-07-25 deposited with the CCDC.	2025-12-29 downloaded from the CCDC.
;
_audit_creation_date             2025-05-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H27 B Br F N2 O3, C3 H7'
_chemical_formula_sum            'C21 H34 B Br F N2 O3'
_chemical_formula_weight         472.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNBFBrO
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.3295(2)
_cell_length_b                   22.0996(3)
_cell_length_c                   10.3207(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.717(2)
_cell_angle_gamma                90
_cell_volume                     2347.32(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12258
_cell_measurement_temperature    99.9(7)
_cell_measurement_theta_max      73.4170
_cell_measurement_theta_min      3.9520
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.620
_exptl_absorpt_coefficient_mu    2.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.142a (Rigaku Oxford Diffraction, 2024)
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    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             988
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.005
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            22936
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.487
_diffrn_reflns_theta_min         4.001
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(7)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -77.00   0.50    2.00    --  -47.48-129.00 -89.00   78
  2  ω    -69.00 -43.00   0.50    2.00    --  -47.48 129.00 -17.00   52
  3  ω   -115.00 -88.00   0.50    2.00    --  -47.48-142.00  98.00   54
  4  ω     56.00 104.00   0.50    2.00    --   47.48-142.00  98.00   96
  5  ω     60.00  85.00   0.50    2.00    --   47.48-129.00 -89.00   50
  6  ω    -65.00 -40.00   0.50    8.00    --  -91.75 142.00 154.00   50
  7  ω   -133.00-108.00   0.50    8.00    --  -91.75-142.00  98.00   50
  8  ω    -97.00 -72.00   0.50    8.00    --  -91.75-129.00 -89.00   50
  9  ω   -162.00-102.00   0.50    8.00    --  -91.75-129.00 -89.00  120
 10  ω     82.00 107.00   0.50    8.00    --  103.50-129.00 -89.00   50
 11  ω     93.00 139.00   0.50    8.00    --  103.50 142.00 154.00   92
 12  ω    111.00 137.00   0.50    8.00    --  103.50 129.00 -17.00   52
 13  ω     97.00 122.00   0.50    8.00    --  103.50-142.00  98.00   50
 14  ω    -12.00  28.00   0.50    2.00    --  -47.48  19.00   0.00   80
 15  ω    -11.00  28.00   0.50    2.00    --  -47.48  19.00-120.00   78
 16  ω    -10.00  27.00   0.50    2.00    --  -47.48  19.00-180.00   74
 17  ω    -71.00 -39.00   0.50    2.00    --  -47.48 142.00 154.00   64
 18  ω    -39.00  19.00   0.50    2.00    --  -47.48  38.00 -90.00  116
 19  ω    -12.00  18.00   0.50    2.00    --  -47.48  19.00  60.00   60
 20  ω    -23.00   3.00   0.50    2.00    --   47.48 -19.00-180.00   52
 21  ω    -20.00  11.00   0.50    2.00    --   47.48 -19.00  30.00   62
 22  ω    -27.00   5.00   0.50    2.00    --   47.48 -19.00 -60.00   64
 23  ω   -148.00-111.00   0.50    8.00    --  -91.75 -77.00-180.00   74
 24  ω   -163.00-116.00   0.50    8.00    --  -91.75 -61.00  90.00   94
 25  ω    -49.00 -24.00   0.50    8.00    --  -91.75  45.00 -60.00   50
 26  ω    -49.00 -24.00   0.50    8.00    --  -91.75  45.00 -30.00   50
 27  ω   -163.00-107.00   0.50    8.00    --  -91.75 -61.00   0.00  112
 28  ω    -48.00 -23.00   0.50    8.00    --  -91.75  45.00   0.00   50
 29  ω   -163.00-108.00   0.50    8.00    --  -91.75 -61.00-150.00  110
 30  ω   -158.00-118.00   0.50    8.00    --  -91.75 -95.00 -30.00   80
 31  ω    -46.00 -20.00   0.50    8.00    --  -91.75  45.00-150.00   52
 32  ω    -49.00 -21.00   0.50    8.00    --  -91.75  45.00 150.00   56
 33  ω    -70.00 -19.00   0.50    8.00    --  -91.75  61.00 -30.00  102
 34  ω    -47.00 -20.00   0.50    8.00    --  -91.75  45.00-180.00   54
 35  ω    -49.00 -24.00   0.50    8.00    --  -91.75  45.00  30.00   50
 36  ω    -48.00 -21.00   0.50    8.00    --  -91.75  45.00  90.00   54
 37  ω   -162.00-106.00   0.50    8.00    --  -91.75 -61.00  30.00  112
 38  ω     72.00 103.00   0.50    8.00    --  103.50 -95.00 -60.00   62
 39  ω     38.00  64.00   0.50    8.00    --  103.50 -95.00 -60.00   52
 40  ω     62.00 103.00   0.50    8.00    --  103.50 -95.00 120.00   82
 41  ω     96.00 123.00   0.50    8.00    --  103.50 -77.00 -90.00   54
 42  ω     31.00  83.00   0.50    8.00    --  103.50 -77.00 -90.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1084772000
_diffrn_orient_matrix_UB_12      0.0415226000
_diffrn_orient_matrix_UB_13      0.0019776000
_diffrn_orient_matrix_UB_21      -0.0838129000
_diffrn_orient_matrix_UB_22      -0.0559135000
_diffrn_orient_matrix_UB_23      -0.0075705000
_diffrn_orient_matrix_UB_31      0.0601373000
_diffrn_orient_matrix_UB_32      -0.0030621000
_diffrn_orient_matrix_UB_33      0.1641472000
_diffrn_oxdiff_digest_hkl        
;
4344dd6303dc28050f7f599d4d61dc705c6da1
;
_diffrn_radiation_collimation    0.12
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4050
_reflns_number_total             4457
_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 1.171.43.142a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.082
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         4457
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.089
_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)+(0.0712P)²+2.9569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1307
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C19(H19A,H19B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.86931(3) 0.76733(2) 0.56639(3) 0.03225(14) Uani 1 1 d . . . . .
F1 F 0.91617(19) 0.66570(9) 0.4066(2) 0.0426(5) Uani 1 1 d . . . . .
O1 O 0.35835(19) 0.83287(8) 0.3429(2) 0.0218(4) Uani 1 1 d . . . . .
O2 O 0.5671(2) 0.88952(8) 0.42819(19) 0.0234(4) Uani 1 1 d . . . . .
O3 O 0.49816(19) 0.83678(8) 0.21422(19) 0.0209(4) Uani 1 1 d . . . . .
N1 N 0.4456(2) 0.75166(10) 0.4759(2) 0.0194(5) Uani 1 1 d . . . . .
H1 H 0.444349 0.718214 0.521540 0.023 Uiso 1 1 calc R U . . .
N2 N 0.2337(2) 0.78139(10) 0.4304(3) 0.0222(5) Uani 1 1 d . . . . .
C1 C 0.6104(3) 0.72424(11) 0.3903(3) 0.0181(5) Uani 1 1 d . . . . .
C2 C 0.7434(3) 0.71685(13) 0.4280(3) 0.0233(6) Uani 1 1 d . . . . .
C3 C 0.7869(3) 0.67126(14) 0.3678(3) 0.0285(6) Uani 1 1 d . . . . .
C4 C 0.7037(3) 0.63195(13) 0.2689(3) 0.0303(7) Uani 1 1 d . . . . .
H4 H 0.735868 0.600937 0.228536 0.036 Uiso 1 1 calc R U . . .
C5 C 0.5715(3) 0.63866(12) 0.2293(3) 0.0261(6) Uani 1 1 d . . . . .
H5 H 0.511715 0.611923 0.161294 0.031 Uiso 1 1 calc R U . . .
C6 C 0.5265(3) 0.68441(12) 0.2889(3) 0.0211(5) Uani 1 1 d . . . . .
H6 H 0.435513 0.688728 0.259730 0.025 Uiso 1 1 calc R U . . .
C7 C 0.5597(3) 0.77294(11) 0.4558(3) 0.0185(5) Uani 1 1 d . . . . .
H7 H 0.629547 0.784551 0.550481 0.022 Uiso 1 1 calc R U . . .
C8 C 0.3446(3) 0.78865(12) 0.4172(3) 0.0189(5) Uani 1 1 d . . . . .
C9 C 0.2132(3) 0.72776(13) 0.5036(3) 0.0267(6) Uani 1 1 d . . . . .
H9A H 0.140437 0.735778 0.530638 0.032 Uiso 1 1 calc R U . . .
H9B H 0.292243 0.720440 0.592266 0.032 Uiso 1 1 calc R U . . .
C10 C 0.1829(3) 0.67181(14) 0.4110(4) 0.0335(7) Uani 1 1 d . . . . .
H10A H 0.102301 0.678142 0.325297 0.050 Uiso 1 1 calc R U . . .
H10B H 0.172480 0.637102 0.464393 0.050 Uiso 1 1 calc R U . . .
H10C H 0.254317 0.663928 0.383278 0.050 Uiso 1 1 calc R U . . .
C11 C 0.1283(3) 0.82581(14) 0.3711(3) 0.0275(6) Uani 1 1 d . . . . .
H11A H 0.043680 0.804501 0.333660 0.033 Uiso 1 1 calc R U . . .
H11B H 0.135677 0.847304 0.290643 0.033 Uiso 1 1 calc R U . . .
C12 C 0.1326(3) 0.87133(15) 0.4825(4) 0.0381(8) Uani 1 1 d . . . . .
H12A H 0.057645 0.898506 0.441669 0.057 Uiso 1 1 calc R U . . .
H12B H 0.212960 0.894983 0.513565 0.057 Uiso 1 1 calc R U . . .
H12C H 0.130061 0.849995 0.564567 0.057 Uiso 1 1 calc R U . . .
C13 C 0.5588(3) 0.93234(12) 0.3196(3) 0.0263(6) Uani 1 1 d . . . . .
C14 C 0.5676(3) 0.89035(12) 0.2027(3) 0.0236(6) Uani 1 1 d . . . . .
C15 C 0.4285(4) 0.96562(13) 0.2682(3) 0.0333(7) Uani 1 1 d . . . . .
H15A H 0.357449 0.936931 0.220474 0.050 Uiso 1 1 calc R U . . .
H15B H 0.425572 0.997580 0.201112 0.050 Uiso 1 1 calc R U . . .
H15C H 0.419019 0.983622 0.350117 0.050 Uiso 1 1 calc R U . . .
C16 C 0.6693(4) 0.97720(14) 0.3834(4) 0.0374(8) Uani 1 1 d . . . . .
H16A H 0.656375 1.001729 0.455504 0.056 Uiso 1 1 calc R U . . .
H16B H 0.671204 1.003613 0.308009 0.056 Uiso 1 1 calc R U . . .
H16C H 0.751806 0.955283 0.427915 0.056 Uiso 1 1 calc R U . . .
C17 C 0.5031(3) 0.91563(13) 0.0530(3) 0.0307(7) Uani 1 1 d . . . . .
H17A H 0.511632 0.886569 -0.014308 0.046 Uiso 1 1 calc R U . . .
H17B H 0.545106 0.953793 0.048061 0.046 Uiso 1 1 calc R U . . .
H17C H 0.410858 0.922908 0.028268 0.046 Uiso 1 1 calc R U . . .
C18 C 0.7068(3) 0.87143(14) 0.2354(4) 0.0325(7) Uani 1 1 d . . . . .
H18A H 0.750513 0.858487 0.335110 0.049 Uiso 1 1 calc R U . . .
H18B H 0.753675 0.905798 0.219213 0.049 Uiso 1 1 calc R U . . .
H18C H 0.705615 0.837878 0.172755 0.049 Uiso 1 1 calc R U . . .
B1 B 0.5046(3) 0.83495(14) 0.3571(3) 0.0206(6) Uani 1 1 d . . . . .
C19 C -0.0245(5) 1.01645(18) 0.0456(5) 0.0575(11) Uani 1 1 d . . . . .
H19A H -0.120178 1.019584 -0.006007 0.069 Uiso 1 1 calc R U . . .
H19B H 0.010789 1.058102 0.059192 0.069 Uiso 1 1 calc R U . . .
C20 C 0.0061(7) 0.9902(2) 0.1878(6) 0.0788(16) Uani 1 1 d . . . . .
H20A H 0.101173 0.983718 0.236435 0.095 Uiso 1 1 calc R U . . .
H20B H -0.035870 0.949953 0.174361 0.095 Uiso 1 1 calc R U . . .
C21 C -0.0344(6) 1.0265(2) 0.2838(6) 0.0742(14) Uani 1 1 d . . . . .
H21A H -0.008837 1.005373 0.375089 0.111 Uiso 1 1 calc R U . . .
H21B H -0.128981 1.031760 0.239331 0.111 Uiso 1 1 calc R U . . .
H21C H 0.007800 1.066194 0.300221 0.111 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 C2 1.901(3) . ?
F1 C3 1.353(3) . ?
O1 C8 1.291(3) . ?
O1 B1 1.602(4) . ?
O2 C13 1.440(3) . ?
O2 B1 1.435(4) . ?
O3 C14 1.453(3) . ?
O3 B1 1.446(3) . ?
N1 H1 0.8800 . ?
N1 C7 1.469(3) . ?
N1 C8 1.329(4) . ?
N2 C8 1.328(4) . ?
N2 C9 1.476(4) . ?
N2 C11 1.468(4) . ?
C1 C2 1.399(4) . ?
C1 C6 1.393(4) . ?
C1 C7 1.507(3) . ?
C2 C3 1.379(4) . ?
C3 C4 1.371(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(4) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 B1 1.665(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.512(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.514(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.558(4) . ?
C13 C15 1.532(5) . ?
C13 C16 1.515(4) . ?
C14 C17 1.513(4) . ?
C14 C18 1.527(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C19 1.470(8) 3_575 ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.479(7) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.489(8) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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 O1 B1 110.2(2) . . ?
B1 O2 C13 107.3(2) . . ?
B1 O3 C14 107.9(2) . . ?
C7 N1 H1 123.8 . . ?
C8 N1 H1 123.8 . . ?
C8 N1 C7 112.3(2) . . ?
C8 N2 C9 120.5(2) . . ?
C8 N2 C11 121.1(2) . . ?
C11 N2 C9 118.4(2) . . ?
C2 C1 C7 121.8(2) . . ?
C6 C1 C2 116.9(2) . . ?
C6 C1 C7 121.3(2) . . ?
C1 C2 Br1 121.5(2) . . ?
C3 C2 Br1 118.0(2) . . ?
C3 C2 C1 120.4(3) . . ?
F1 C3 C2 118.7(3) . . ?
F1 C3 C4 119.0(3) . . ?
C4 C3 C2 122.3(3) . . ?
C3 C4 H4 120.9 . . ?
C3 C4 C5 118.3(3) . . ?
C5 C4 H4 120.9 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 H6 118.9 . . ?
C5 C6 C1 122.1(3) . . ?
C5 C6 H6 118.9 . . ?
N1 C7 C1 111.0(2) . . ?
N1 C7 H7 109.1 . . ?
N1 C7 B1 102.9(2) . . ?
C1 C7 H7 109.1 . . ?
C1 C7 B1 115.4(2) . . ?
B1 C7 H7 109.1 . . ?
O1 C8 N1 116.2(2) . . ?
O1 C8 N2 120.4(2) . . ?
N2 C8 N1 123.4(2) . . ?
N2 C9 H9A 109.2 . . ?
N2 C9 H9B 109.2 . . ?
N2 C9 C10 112.1(2) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 H11A 109.3 . . ?
N2 C11 H11B 109.3 . . ?
N2 C11 C12 111.4(3) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 C14 101.9(2) . . ?
O2 C13 C15 108.9(2) . . ?
O2 C13 C16 108.6(2) . . ?
C15 C13 C14 112.5(2) . . ?
C16 C13 C14 114.7(2) . . ?
C16 C13 C15 109.8(3) . . ?
O3 C14 C13 102.1(2) . . ?
O3 C14 C17 109.7(2) . . ?
O3 C14 C18 107.6(2) . . ?
C17 C14 C13 114.3(2) . . ?
C17 C14 C18 109.8(2) . . ?
C18 C14 C13 112.7(2) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 B1 C7 98.10(19) . . ?
O2 B1 O1 109.9(2) . . ?
O2 B1 O3 107.6(2) . . ?
O2 B1 C7 113.6(2) . . ?
O3 B1 O1 107.3(2) . . ?
O3 B1 C7 119.5(2) . . ?
C19 C19 H19A 108.2 3_575 . ?
C19 C19 H19B 108.2 3_575 . ?
C19 C19 C20 116.5(5) 3_575 . ?
H19A C19 H19B 107.3 . . ?
C20 C19 H19A 108.2 . . ?
C20 C19 H19B 108.2 . . ?
C19 C20 H20A 108.3 . . ?
C19 C20 H20B 108.3 . . ?
C19 C20 C21 116.0(4) . . ?
H20A C20 H20B 107.4 . . ?
C21 C20 H20A 108.3 . . ?
C21 C20 H20B 108.3 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
Br1 C2 C3 F1 -1.9(4) . . . . ?
Br1 C2 C3 C4 178.9(2) . . . . ?
F1 C3 C4 C5 -179.4(3) . . . . ?
O2 C13 C14 O3 35.2(3) . . . . ?
O2 C13 C14 C17 153.7(2) . . . . ?
O2 C13 C14 C18 -80.0(3) . . . . ?
N1 C7 B1 O1 -0.6(2) . . . . ?
N1 C7 B1 O2 115.3(2) . . . . ?
N1 C7 B1 O3 -115.9(3) . . . . ?
C1 C2 C3 F1 179.8(2) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C1 C7 B1 O1 120.4(2) . . . . ?
C1 C7 B1 O2 -123.7(3) . . . . ?
C1 C7 B1 O3 5.1(4) . . . . ?
C2 C1 C6 C5 1.1(4) . . . . ?
C2 C1 C7 N1 -144.1(2) . . . . ?
C2 C1 C7 B1 99.4(3) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
C6 C1 C2 Br1 -179.30(18) . . . . ?
C6 C1 C2 C3 -1.0(4) . . . . ?
C6 C1 C7 N1 35.9(3) . . . . ?
C6 C1 C7 B1 -80.6(3) . . . . ?
C7 N1 C8 O1 6.1(3) . . . . ?
C7 N1 C8 N2 -174.9(2) . . . . ?
C7 C1 C2 Br1 0.7(3) . . . . ?
C7 C1 C2 C3 179.0(2) . . . . ?
C7 C1 C6 C5 -178.9(2) . . . . ?
C8 O1 B1 O2 -114.9(2) . . . . ?
C8 O1 B1 O3 128.4(2) . . . . ?
C8 O1 B1 C7 3.9(2) . . . . ?
C8 N1 C7 C1 -126.7(2) . . . . ?
C8 N1 C7 B1 -2.8(3) . . . . ?
C8 N2 C9 C10 -76.8(3) . . . . ?
C8 N2 C11 C12 -95.5(3) . . . . ?
C9 N2 C8 O1 174.2(2) . . . . ?
C9 N2 C8 N1 -4.8(4) . . . . ?
C9 N2 C11 C12 85.3(3) . . . . ?
C11 N2 C8 O1 -5.0(4) . . . . ?
C11 N2 C8 N1 176.0(2) . . . . ?
C11 N2 C9 C10 102.4(3) . . . . ?
C13 O2 B1 O1 -97.6(2) . . . . ?
C13 O2 B1 O3 19.0(3) . . . . ?
C13 O2 B1 C7 153.6(2) . . . . ?
C14 O3 B1 O1 123.3(2) . . . . ?
C14 O3 B1 O2 5.0(3) . . . . ?
C14 O3 B1 C7 -126.4(3) . . . . ?
C15 C13 C14 O3 -81.3(3) . . . . ?
C15 C13 C14 C17 37.1(3) . . . . ?
C15 C13 C14 C18 163.5(2) . . . . ?
C16 C13 C14 O3 152.4(3) . . . . ?
C16 C13 C14 C17 -89.2(3) . . . . ?
C16 C13 C14 C18 37.1(3) . . . . ?
B1 O1 C8 N1 -6.4(3) . . . . ?
B1 O1 C8 N2 174.5(2) . . . . ?
B1 O2 C13 C14 -33.3(3) . . . . ?
B1 O2 C13 C15 85.7(3) . . . . ?
B1 O2 C13 C16 -154.8(2) . . . . ?
B1 O3 C14 C13 -24.7(3) . . . . ?
B1 O3 C14 C17 -146.3(2) . . . . ?
B1 O3 C14 C18 94.2(3) . . . . ?
C19 C19 C20 C21 175.1(6) 3_575 . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_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 2.080
_oxdiff_exptl_absorpt_empirical_full_min 0.562
