# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

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

data_exp42241
_database_code_depnum_ccdc_archive 'CCDC 2055623'
loop_
_audit_author_name
_audit_author_address
'Manju Rajeswaran'
;Columbia University
United States of America
;
_audit_update_record             
;
2021-01-12 deposited with the CCDC.	2021-03-22 downloaded from the CCDC.
;
_audit_creation_date             2020-12-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H19 B Br N O5'
_chemical_formula_sum            'C16 H19 B Br N O5'
_chemical_formula_weight         396.04
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H19 B1 Br1 N1 O5'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   16.8549(14)
_cell_length_b                   9.7346(7)
_cell_length_c                   10.8047(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.873(8)
_cell_angle_gamma                90
_cell_volume                     1728.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1297
_cell_measurement_temperature    291.90(16)
_cell_measurement_theta_max      22.3620
_cell_measurement_theta_min      4.0990
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.404
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7907
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.423
_diffrn_reflns_theta_min         3.275
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.90(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0549
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     40.00  73.00   1.00   12.50    --   17.04-138.00 176.00   33
  2  ω     42.00  76.00   1.00   12.50    --   17.04 178.00 150.00   34
  3  ω    -16.00  10.00   1.00   12.50    --   17.04 -37.00-180.00   26
  4  ω    -38.00  85.00   1.00   12.50    --   17.04   0.00  60.00  123
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0384731000
_diffrn_orient_matrix_UB_12      0.0318063000
_diffrn_orient_matrix_UB_13      -0.0214046000
_diffrn_orient_matrix_UB_21      -0.0195158000
_diffrn_orient_matrix_UB_22      -0.0611144000
_diffrn_orient_matrix_UB_23      0.0131643000
_diffrn_orient_matrix_UB_31      0.0012864000
_diffrn_orient_matrix_UB_32      0.0237402000
_diffrn_orient_matrix_UB_33      0.0624795000
_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_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2160
_reflns_number_total             4000
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4000
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1355
_refine_ls_R_factor_gt           0.0664
_refine_ls_restrained_S_all      1.018
_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)+(0.0513P)²+1.3302P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1582
_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 Ternary CH refined with riding coordinates:
 C009(H009), C00G(H00J), C00I(H00K)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00C(H00C,H00D), C00D(H00E,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 C00K(H00O), C00M(H00P), C00N(H00Q), C00O(H00R)
2.d Idealised Me refined as rotating group:
 C00E(H00G,H00H,H00I), C00J(H00L,H00M,H00N)
;
_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
Br01 Br 0.80587(4) 0.99773(6) 0.50436(6) 0.0726(3) Uani 1 1 d . . . . .
O002 O 0.55132(17) 0.6297(3) 0.2012(2) 0.0447(7) Uani 1 1 d . . . . .
O003 O 0.59609(17) 0.5984(3) 0.4291(3) 0.0441(7) Uani 1 1 d . . . . .
O004 O 0.43723(18) 0.5467(3) 0.0775(3) 0.0526(8) Uani 1 1 d . . . . .
O005 O 0.76654(18) 0.5957(3) 0.3995(3) 0.0556(8) Uani 1 1 d . . . . .
N006 N 0.61423(19) 0.4163(3) 0.2891(3) 0.0365(8) Uani 1 1 d . . . . .
O007 O 0.5933(2) 0.4735(4) 0.6028(3) 0.0663(10) Uani 1 1 d . . . . .
C008 C 0.5002(3) 0.5301(5) 0.1558(4) 0.0404(10) Uani 1 1 d . . . . .
C009 C 0.7011(3) 0.6562(5) 0.3021(4) 0.0439(11) Uani 1 1 d . . . . .
H009 H 0.713409 0.643626 0.218328 0.053 Uiso 1 1 calc R U . . .
C00A C 0.6032(3) 0.4834(5) 0.4959(4) 0.0468(12) Uani 1 1 d . . . . .
C00B C 0.5285(3) 0.3943(4) 0.2151(4) 0.0432(10) Uani 1 1 d . . . . .
H00A H 0.527099 0.324956 0.150211 0.052 Uiso 1 1 calc R U . . .
H00B H 0.494038 0.364708 0.270891 0.052 Uiso 1 1 calc R U . . .
C00C C 0.6273(3) 0.3659(5) 0.4217(4) 0.0513(12) Uani 1 1 d . . . . .
H00C H 0.683963 0.341564 0.454189 0.062 Uiso 1 1 calc R U . . .
H00D H 0.593852 0.285845 0.426412 0.062 Uiso 1 1 calc R U . . .
C00D C 0.7021(3) 0.8097(5) 0.3334(4) 0.0524(12) Uani 1 1 d . . . . .
H00E H 0.690936 0.865325 0.257027 0.063 Uiso 1 1 calc R U . . .
H00F H 0.663201 0.831772 0.384361 0.063 Uiso 1 1 calc R U . . .
C00E C 0.6733(3) 0.3559(5) 0.2197(4) 0.0537(12) Uani 1 1 d . . . . .
H00G H 0.666762 0.257919 0.215343 0.081 Uiso 1 1 calc R U . . .
H00H H 0.727771 0.377986 0.263783 0.081 Uiso 1 1 calc R U . . .
H00I H 0.663287 0.392982 0.135293 0.081 Uiso 1 1 calc R U . . .
C00F C 0.8907(3) 0.6607(5) 0.5449(4) 0.0516(12) Uani 1 1 d . . . . .
C00G C 0.8056(3) 0.7025(5) 0.4847(5) 0.0600(13) Uani 1 1 d . . . . .
H00J H 0.775938 0.710002 0.552729 0.072 Uiso 1 1 calc R U . . .
B00H B 0.6184(3) 0.5839(5) 0.3048(4) 0.0360(11) Uani 1 1 d . . . . .
C00I C 0.7886(3) 0.8283(5) 0.4077(5) 0.0616(14) Uani 1 1 d . . . . .
H00K H 0.824318 0.829127 0.347433 0.074 Uiso 1 1 calc R U . . .
C00J C 0.8433(4) 0.4578(7) 0.6502(6) 0.093(2) Uani 1 1 d . . . . .
H00L H 0.794664 0.509317 0.649618 0.140 Uiso 1 1 calc R U . . .
H00M H 0.861382 0.414263 0.731313 0.140 Uiso 1 1 calc R U . . .
H00N H 0.832181 0.388981 0.584926 0.140 Uiso 1 1 calc R U . . .
C00K C 0.9580(3) 0.7366(7) 0.5265(5) 0.086(2) Uani 1 1 d . . . . .
H00O H 0.947997 0.813138 0.473834 0.103 Uiso 1 1 calc R U . . .
C00L C 0.9065(4) 0.5498(7) 0.6270(5) 0.0759(17) Uani 1 1 d . . . . .
C00M C 0.9883(4) 0.5176(8) 0.6873(6) 0.093(2) Uani 1 1 d . . . . .
H00P H 0.999533 0.444802 0.744280 0.112 Uiso 1 1 calc R U . . .
C00N C 1.0493(5) 0.5934(10) 0.6610(7) 0.105(3) Uani 1 1 d . . . . .
H00Q H 1.102611 0.569193 0.698794 0.126 Uiso 1 1 calc R U . . .
C00O C 1.0365(4) 0.7059(10) 0.5801(8) 0.111(3) Uani 1 1 d . . . . .
H00R H 1.079440 0.757461 0.563699 0.133 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
Br01 C00I 1.939(5) . ?
O002 C008 1.317(5) . ?
O002 B00H 1.472(5) . ?
O003 C00A 1.323(5) . ?
O003 B00H 1.481(5) . ?
O004 C008 1.212(5) . ?
O005 C009 1.467(5) . ?
O005 C00G 1.447(5) . ?
N006 C00B 1.502(5) . ?
N006 C00C 1.483(5) . ?
N006 C00E 1.494(5) . ?
N006 B00H 1.641(6) . ?
O007 C00A 1.207(5) . ?
C008 C00B 1.500(6) . ?
C009 H009 0.9800 . ?
C009 C00D 1.531(6) . ?
C009 B00H 1.568(6) . ?
C00A C00C 1.504(6) . ?
C00B H00A 0.9700 . ?
C00B H00B 0.9700 . ?
C00C H00C 0.9700 . ?
C00C H00D 0.9700 . ?
C00D H00E 0.9700 . ?
C00D H00F 0.9700 . ?
C00D C00I 1.510(6) . ?
C00E H00G 0.9600 . ?
C00E H00H 0.9600 . ?
C00E H00I 0.9600 . ?
C00F C00G 1.494(6) . ?
C00F C00K 1.405(7) . ?
C00F C00L 1.384(7) . ?
C00G H00J 0.9800 . ?
C00G C00I 1.472(7) . ?
C00I H00K 0.9800 . ?
C00J H00L 0.9600 . ?
C00J H00M 0.9600 . ?
C00J H00N 0.9600 . ?
C00J C00L 1.456(9) . ?
C00K H00O 0.9300 . ?
C00K C00O 1.354(8) . ?
C00L C00M 1.423(8) . ?
C00M H00P 0.9300 . ?
C00M C00N 1.347(10) . ?
C00N H00Q 0.9300 . ?
C00N C00O 1.388(10) . ?
C00O H00R 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C008 O002 B00H 112.8(3) . . ?
C00A O003 B00H 113.8(3) . . ?
C00G O005 C009 109.3(3) . . ?
C00B N006 B00H 102.1(3) . . ?
C00C N006 C00B 112.7(3) . . ?
C00C N006 C00E 112.5(3) . . ?
C00C N006 B00H 103.6(3) . . ?
C00E N006 C00B 110.2(3) . . ?
C00E N006 B00H 115.1(3) . . ?
O002 C008 C00B 111.7(3) . . ?
O004 C008 O002 124.1(4) . . ?
O004 C008 C00B 124.2(4) . . ?
O005 C009 H009 109.4 . . ?
O005 C009 C00D 105.3(3) . . ?
O005 C009 B00H 109.6(3) . . ?
C00D C009 H009 109.4 . . ?
C00D C009 B00H 113.6(4) . . ?
B00H C009 H009 109.4 . . ?
O003 C00A C00C 110.8(4) . . ?
O007 C00A O003 125.0(4) . . ?
O007 C00A C00C 124.2(4) . . ?
N006 C00B H00A 110.5 . . ?
N006 C00B H00B 110.5 . . ?
C008 C00B N006 106.2(3) . . ?
C008 C00B H00A 110.5 . . ?
C008 C00B H00B 110.5 . . ?
H00A C00B H00B 108.7 . . ?
N006 C00C C00A 105.3(4) . . ?
N006 C00C H00C 110.7 . . ?
N006 C00C H00D 110.7 . . ?
C00A C00C H00C 110.7 . . ?
C00A C00C H00D 110.7 . . ?
H00C C00C H00D 108.8 . . ?
C009 C00D H00E 111.5 . . ?
C009 C00D H00F 111.5 . . ?
H00E C00D H00F 109.3 . . ?
C00I C00D C009 101.3(4) . . ?
C00I C00D H00E 111.5 . . ?
C00I C00D H00F 111.5 . . ?
N006 C00E H00G 109.5 . . ?
N006 C00E H00H 109.5 . . ?
N006 C00E H00I 109.5 . . ?
H00G C00E H00H 109.5 . . ?
H00G C00E H00I 109.5 . . ?
H00H C00E H00I 109.5 . . ?
C00K C00F C00G 121.5(5) . . ?
C00L C00F C00G 121.4(5) . . ?
C00L C00F C00K 117.1(5) . . ?
O005 C00G C00F 109.7(4) . . ?
O005 C00G H00J 107.1 . . ?
O005 C00G C00I 103.6(4) . . ?
C00F C00G H00J 107.1 . . ?
C00I C00G C00F 121.4(4) . . ?
C00I C00G H00J 107.1 . . ?
O002 B00H O003 110.7(3) . . ?
O002 B00H N006 102.4(3) . . ?
O002 B00H C009 112.7(4) . . ?
O003 B00H N006 100.1(3) . . ?
O003 B00H C009 112.4(3) . . ?
C009 B00H N006 117.6(3) . . ?
Br01 C00I H00K 108.1 . . ?
C00D C00I Br01 113.6(4) . . ?
C00D C00I H00K 108.1 . . ?
C00G C00I Br01 114.6(3) . . ?
C00G C00I C00D 104.1(4) . . ?
C00G C00I H00K 108.1 . . ?
H00L C00J H00M 109.5 . . ?
H00L C00J H00N 109.5 . . ?
H00M C00J H00N 109.5 . . ?
C00L C00J H00L 109.5 . . ?
C00L C00J H00M 109.5 . . ?
C00L C00J H00N 109.5 . . ?
C00F C00K H00O 117.8 . . ?
C00O C00K C00F 124.5(7) . . ?
C00O C00K H00O 117.8 . . ?
C00F C00L C00J 123.2(6) . . ?
C00F C00L C00M 119.6(7) . . ?
C00M C00L C00J 117.2(7) . . ?
C00L C00M H00P 120.3 . . ?
C00N C00M C00L 119.4(7) . . ?
C00N C00M H00P 120.3 . . ?
C00M C00N H00Q 118.5 . . ?
C00M C00N C00O 123.1(7) . . ?
C00O C00N H00Q 118.5 . . ?
C00K C00O C00N 116.4(8) . . ?
C00K C00O H00R 121.8 . . ?
C00N C00O H00R 121.8 . . ?

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
O002 C008 C00B N006 -10.3(4) . . . . ?
O003 C00A C00C N006 -13.6(5) . . . . ?
O004 C008 C00B N006 171.1(4) . . . . ?
O005 C009 C00D C00I 23.6(5) . . . . ?
O005 C009 B00H O002 -174.3(3) . . . . ?
O005 C009 B00H O003 59.8(5) . . . . ?
O005 C009 B00H N006 -55.5(5) . . . . ?
O005 C00G C00I Br01 163.8(3) . . . . ?
O005 C00G C00I C00D 39.2(5) . . . . ?
O007 C00A C00C N006 167.5(4) . . . . ?
C008 O002 B00H O003 -89.6(4) . . . . ?
C008 O002 B00H N006 16.3(4) . . . . ?
C008 O002 B00H C009 143.6(4) . . . . ?
C009 O005 C00G C00F -155.1(4) . . . . ?
C009 O005 C00G C00I -24.1(5) . . . . ?
C009 C00D C00I Br01 -163.9(3) . . . . ?
C009 C00D C00I C00G -38.6(5) . . . . ?
C00A O003 B00H O002 124.9(4) . . . . ?
C00A O003 B00H N006 17.4(4) . . . . ?
C00A O003 B00H C009 -108.1(4) . . . . ?
C00B N006 C00C C00A -86.7(4) . . . . ?
C00B N006 B00H O002 -21.0(4) . . . . ?
C00B N006 B00H O003 93.1(3) . . . . ?
C00B N006 B00H C009 -145.0(3) . . . . ?
C00C N006 C00B C008 129.3(4) . . . . ?
C00C N006 B00H O002 -138.2(3) . . . . ?
C00C N006 B00H O003 -24.2(4) . . . . ?
C00C N006 B00H C009 97.7(4) . . . . ?
C00D C009 B00H O002 68.3(5) . . . . ?
C00D C009 B00H O003 -57.7(5) . . . . ?
C00D C009 B00H N006 -173.0(3) . . . . ?
C00E N006 C00B C008 -104.1(4) . . . . ?
C00E N006 C00C C00A 148.0(4) . . . . ?
C00E N006 B00H O002 98.5(4) . . . . ?
C00E N006 B00H O003 -147.5(3) . . . . ?
C00E N006 B00H C009 -25.5(5) . . . . ?
C00F C00G C00I Br01 -72.5(6) . . . . ?
C00F C00G C00I C00D 162.9(4) . . . . ?
C00F C00K C00O C00N -1.8(9) . . . . ?
C00F C00L C00M C00N -1.7(9) . . . . ?
C00G O005 C009 C00D -0.2(5) . . . . ?
C00G O005 C009 B00H -122.7(4) . . . . ?
C00G C00F C00K C00O 178.6(5) . . . . ?
C00G C00F C00L C00J 6.8(8) . . . . ?
C00G C00F C00L C00M -176.9(5) . . . . ?
B00H O002 C008 O004 173.7(4) . . . . ?
B00H O002 C008 C00B -4.8(5) . . . . ?
B00H O003 C00A O007 175.1(4) . . . . ?
B00H O003 C00A C00C -3.7(5) . . . . ?
B00H N006 C00B C008 18.8(4) . . . . ?
B00H N006 C00C C00A 23.0(4) . . . . ?
B00H C009 C00D C00I 143.5(4) . . . . ?
C00J C00L C00M C00N 174.9(6) . . . . ?
C00K C00F C00G O005 118.2(5) . . . . ?
C00K C00F C00G C00I -2.5(7) . . . . ?
C00K C00F C00L C00J -176.7(5) . . . . ?
C00K C00F C00L C00M -0.4(8) . . . . ?
C00L C00F C00G O005 -65.5(6) . . . . ?
C00L C00F C00G C00I 173.8(5) . . . . ?
C00L C00F C00K C00O 2.2(8) . . . . ?
C00L C00M C00N C00O 2.2(11) . . . . ?
C00M C00N C00O C00K -0.5(11) . . . . ?

_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 1.233
_oxdiff_exptl_absorpt_empirical_full_min 0.887
####################################################################### 
# 
# 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_exp_4258
_database_code_depnum_ccdc_archive 'CCDC 2055627'
loop_
_audit_author_name
_audit_author_address
'Manju Rajeswaran'
;Columbia University
United States of America
;
_audit_update_record             
;
2021-01-12 deposited with the CCDC.	2021-03-22 downloaded from the CCDC.
;
_audit_creation_date             2020-12-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H17 B Br N O5'
_chemical_formula_sum            'C15 H17 B Br N O5'
_chemical_formula_weight         382.01
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H17 B1 Br1 N1 O5'
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'
Br Br -0.6763 1.2805 '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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   11.7731(8)
_cell_length_b                   6.9423(4)
_cell_length_c                   40.482(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3308.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2916
_cell_measurement_temperature    292.11(19)
_cell_measurement_theta_max      59.3940
_cell_measurement_theta_min      4.3720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            22840
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.071
_diffrn_reflns_theta_min         4.369
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.11(19)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1098
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -81.00 -46.00   1.00    1.08    --    0.00 178.00 120.00   35
  2  ω      2.00  36.00   1.00    1.08    --    0.00 -99.00 -30.00   34
  3  ω      1.00  39.00   1.00    1.08    --    0.00 -99.00-180.00   38
  4  ω    -33.00  -5.00   1.00    1.08    --    0.00  77.00 120.00   28
  5  ω     28.00  70.00   1.00    1.08    --    0.00  77.00 120.00   42
  6  ω      4.00  29.00   1.00    1.08    --    0.00 -99.00 150.00   25
  7  ω    -82.00 -35.00   1.00    1.08    --    0.00-178.00 -60.00   47
  8  ω   -115.00 -80.00   1.00    4.34    --  -59.50 -94.00 -60.00   35
  9  ω   -131.00 -80.00   1.00    4.34    --  -59.50 -94.00-120.00   51
 10  ω   -132.00 -83.00   1.00    4.34    --  -59.50 -94.00 -90.00   49
 11  ω    -73.00 -45.00   1.00    4.34    --  -59.50 125.00 -90.00   28
 12  ω   -132.00-103.00   1.00    4.34    --  -59.50-125.00-150.00   29
 13  ω   -129.00 -87.00   1.00    4.34    --  -59.50 -94.00-150.00   42
 14  ω    -84.00 -13.00   1.00    4.34    --  -59.50  73.00  90.00   71
 15  ω     41.00 129.00   1.00    4.34    --   59.50  61.00 -60.00   88
 16  ω    -11.00  35.00   1.00    4.34    --   59.50 -77.00 120.00   46
 17  ω     42.00 117.00   1.00    4.34    --   59.50-125.00-180.00   75
 18  ω     -6.00  25.00   1.00    4.34    --   59.50 -61.00 150.00   31
 19  ω     33.00  83.00   1.00    4.34    --   59.50 -61.00 150.00   50
 20  ω     10.00  87.00   1.00    4.34    --   59.50 -45.00 150.00   77
 21  ω     85.00 112.00   1.00    4.34    --  119.00-111.00 120.00   27
 22  ω    136.00 178.00   1.00    4.34    --  119.00  73.00  90.00   42
 23  ω     94.00 121.00   1.00    4.34    --  119.00  73.00  90.00   27
 24  ω    100.00 145.00   1.00    4.34    --  119.00 -37.00  30.00   45
 25  ω    113.00 161.00   1.00    4.34    --  119.00 -91.00 -30.00   48
 26  ω     44.00 177.00   1.00    4.34    --  119.00   0.00-150.00  133
 27  ω     49.00 144.00   1.00    4.34    --  119.00 -63.00 120.00   95
 28  ω     44.00 150.00   1.00    4.34    --  119.00 -25.00 -90.00  106
 29  ω     88.00 122.00   1.00    4.34    --  119.00  77.00 -90.00   34
 30  ω     61.00 109.00   1.00    4.34    --  119.00-111.00 -60.00   48
 31  ω     48.00 147.00   1.00    4.34    --  119.00 -50.00 -60.00   99
 32  ω     53.00  86.00   1.00    4.34    --  119.00 -91.00 -30.00   33
 33  ω     73.00 112.00   1.00    4.34    --  119.00-111.00-120.00   39
 34  ω     86.00 177.00   1.00    4.34    --  119.00  25.00-120.00   91
 35  ω     88.00 149.00   1.00    4.34    --  119.00 -37.00 120.00   61
 36  ω     69.00 112.00   1.00    4.34    --  119.00-111.00  30.00   43
 37  ω     86.00 111.00   1.00    4.34    --  119.00-111.00 -30.00   25
 38  ω     43.00 112.00   1.00    4.34    --  119.00-111.00 150.00   69
 39  ω    144.00 175.00   1.00    4.34    --  119.00 111.00-180.00   31
 40  ω     48.00  82.00   1.00    4.34    --  119.00-111.00 -30.00   34
 41  ω    131.00 174.00   1.00    4.34    --  119.00  77.00 -90.00   43
 42  ω     53.00  87.00   1.00    4.34    --  119.00 -37.00 120.00   34
 43  ω     83.00 157.00   1.00    4.34    --  119.00 -91.00 150.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0700130000
_diffrn_orient_matrix_UB_12      -0.0948696000
_diffrn_orient_matrix_UB_13      -0.0277071000
_diffrn_orient_matrix_UB_21      0.0306218000
_diffrn_orient_matrix_UB_22      0.2006663000
_diffrn_orient_matrix_UB_23      -0.0136747000
_diffrn_orient_matrix_UB_31      0.1061860000
_diffrn_orient_matrix_UB_32      0.0050911000
_diffrn_orient_matrix_UB_33      0.0221988000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_full    0.887
_reflns_Friedel_fraction_max     0.876
_reflns_number_gt                4919
_reflns_number_total             6312
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.873
_refine_diff_density_min         -0.721
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details 
;
 Flack x determined using 1531 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.32(3)
_refine_ls_extinction_coef       0.00031(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         6312
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0832
_refine_ls_restrained_S_all      1.079
_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)+(0.0950P)²+12.0558P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2259
_refine_ls_wR_factor_ref         0.2401
_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 Ternary CH refined with riding coordinates:
 C00G(H00H), C00J(H00J), C00N(H00N), C00U(H00U), C00W(H00W), C016(H016)
2.b Secondary CH2 refined with riding coordinates:
 C00H(H00I,H00K), C00M(H00M,H00O), C00O(H00A,H00B), C00P(H00P,H00Q), C00V(H00F,
 H00G), C011(H01A,H01B)
2.c Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00Q(H00R), C00X(H00X), C00Y(H00Y), C010(H010), C014(H014),
 C017(H017), C018(H018), C019(H019), C01A(H01C)
2.d Idealised Me refined as rotating group:
 C00S(H00C,H00D,H00E), C00Z(H00S,H00T,H00V)
;
_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
Br01 Br 0.83272(17) -0.1613(2) 0.66985(5) 0.0760(6) Uani 1 1 d . . . . .
Br02 Br 0.42865(17) 0.6690(2) 0.33347(5) 0.0759(6) Uani 1 1 d . . . . .
O003 O 0.7670(8) 0.2258(14) 0.5589(3) 0.051(2) Uani 1 1 d . . . . .
O004 O 0.5048(8) 0.2777(14) 0.4444(2) 0.046(2) Uani 1 1 d . . . . .
O005 O 0.6020(8) 0.2317(17) 0.3752(3) 0.060(3) Uani 1 1 d . . . . .
O006 O 0.8868(8) 0.5035(15) 0.5709(3) 0.054(2) Uani 1 1 d . . . . .
O007 O 0.3831(8) 0.0039(16) 0.4314(3) 0.058(3) Uani 1 1 d . . . . .
O008 O 0.9413(10) 0.7427(17) 0.5374(3) 0.068(3) Uani 1 1 d . . . . .
O009 O 0.6686(7) 0.2883(18) 0.6282(3) 0.058(3) Uani 1 1 d . . . . .
O00A O 0.6272(10) 0.0896(14) 0.5290(3) 0.063(3) Uani 1 1 d . . . . .
N00B N 0.5865(9) -0.0320(14) 0.4359(3) 0.043(2) Uani 1 1 d . . . . .
O00C O 0.6404(10) 0.4160(15) 0.4742(3) 0.065(3) Uani 1 1 d . . . . .
O00D O 0.3327(10) -0.238(2) 0.4642(4) 0.080(4) Uani 1 1 d . . . . .
N00E N 0.6828(8) 0.5368(14) 0.5665(3) 0.042(2) Uani 1 1 d . . . . .
C00F C 0.8668(12) 0.643(2) 0.5484(4) 0.051(3) Uani 1 1 d . . . . .
C00G C 0.4879(10) 0.1647(17) 0.3846(3) 0.042(3) Uani 1 1 d . . . . .
H00H H 0.466566 0.051185 0.371640 0.051 Uiso 1 1 calc R . . . .
C00H C 0.4119(11) 0.336(2) 0.3757(4) 0.051(3) Uani 1 1 d . . . . .
H00I H 0.334062 0.296114 0.371824 0.062 Uiso 1 1 calc R . . . .
H00K H 0.413213 0.434151 0.392773 0.062 Uiso 1 1 calc R . . . .
C00I C 0.6637(12) 0.341(2) 0.3215(4) 0.050(3) Uani 1 1 d . . . . .
C00J C 0.6715(11) 0.133(2) 0.6506(4) 0.050(3) Uani 1 1 d . . . . .
H00J H 0.643236 0.018091 0.639286 0.060 Uiso 1 1 calc R . . . .
C00K C 0.6614(11) 0.222(2) 0.5449(4) 0.045(3) Uani 1 1 d . . . . .
C00L C 0.7835(19) 0.277(4) 0.2636(5) 0.083(6) Uani 1 1 d . . . . .
H00L H 0.821730 0.254870 0.243840 0.100 Uiso 1 1 calc R . . . .
C00M C 0.5294(12) -0.143(2) 0.4626(4) 0.051(3) Uani 1 1 d . . . . .
H00M H 0.542145 -0.084082 0.483995 0.061 Uiso 1 1 calc R . . . .
H00O H 0.556655 -0.275109 0.463235 0.061 Uiso 1 1 calc R . . . .
C00N C 0.7984(12) 0.103(2) 0.6584(3) 0.050(3) Uani 1 1 d . . . . .
H00N H 0.820184 0.187327 0.676788 0.060 Uiso 1 1 calc R . . . .
C00O C 0.8550(12) 0.174(2) 0.6270(4) 0.051(3) Uani 1 1 d . . . . .
H00A H 0.933148 0.211564 0.630980 0.061 Uiso 1 1 calc R . . . .
H00B H 0.852945 0.076732 0.609820 0.061 Uiso 1 1 calc R . . . .
C00P C 0.6735(11) 0.105(2) 0.4493(4) 0.048(3) Uani 1 1 d . . . . .
H00P H 0.731196 0.132996 0.432877 0.058 Uiso 1 1 calc R . . . .
H00Q H 0.709873 0.052323 0.468802 0.058 Uiso 1 1 calc R . . . .
C00Q C 0.6767(13) 0.164(2) 0.3091(4) 0.055(3) Uani 1 1 d . . . . .
H00R H 0.643405 0.060416 0.319959 0.066 Uiso 1 1 calc R . . . .
C00R C 0.6070(13) 0.283(2) 0.4577(4) 0.051(3) Uani 1 1 d . . . . .
C00S C 0.6378(13) 0.6752(19) 0.5915(4) 0.054(3) Uani 1 1 d . . . . .
H00C H 0.578176 0.750763 0.581814 0.081 Uiso 1 1 calc GR . . . .
H00D H 0.697867 0.758731 0.598729 0.081 Uiso 1 1 calc GR . . . .
H00E H 0.608363 0.605232 0.610093 0.081 Uiso 1 1 calc GR . . . .
C00T C 0.6012(12) 0.165(2) 0.6806(4) 0.055(4) Uani 1 1 d . . . . .
C00U C 0.4675(13) 0.405(2) 0.3445(4) 0.058(4) Uani 1 1 d . . . . .
H00U H 0.446277 0.320308 0.326208 0.069 Uiso 1 1 calc R . . . .
C00V C 0.5961(11) 0.400(2) 0.5533(3) 0.049(3) Uani 1 1 d . . . . .
H00F H 0.559498 0.453280 0.533844 0.059 Uiso 1 1 calc R . . . .
H00G H 0.538583 0.373202 0.569816 0.059 Uiso 1 1 calc R . . . .
C00W C 0.5936(12) 0.383(2) 0.3518(4) 0.052(3) Uani 1 1 d . . . . .
H00W H 0.621481 0.501641 0.361974 0.063 Uiso 1 1 calc R . . . .
C00X C 0.5380(16) 0.018(3) 0.6940(4) 0.074(5) Uani 1 1 d . . . . .
H00X H 0.538412 -0.101086 0.683479 0.089 Uiso 1 1 calc R . . . .
C00Y C 0.7386(18) 0.129(4) 0.2802(4) 0.080(6) Uani 1 1 d . . . . .
H00Y H 0.748409 0.003956 0.272614 0.096 Uiso 1 1 calc R . . . .
C00Z C 0.6326(14) -0.166(2) 0.4106(4) 0.060(4) Uani 1 1 d . . . . .
H00S H 0.687600 -0.249482 0.420668 0.089 Uiso 1 1 calc GR . . . .
H00T H 0.668023 -0.093276 0.393289 0.089 Uiso 1 1 calc GR . . . .
H00V H 0.571799 -0.241654 0.401599 0.089 Uiso 1 1 calc GR . . . .
C010 C 0.4744(17) 0.040(3) 0.7221(5) 0.081(6) Uani 1 1 d . . . . .
H010 H 0.434982 -0.063944 0.730940 0.097 Uiso 1 1 calc R . . . .
C011 C 0.7433(11) 0.6462(19) 0.5390(4) 0.047(3) Uani 1 1 d . . . . .
H01A H 0.731583 0.583493 0.517864 0.057 Uiso 1 1 calc R . . . .
H01B H 0.715531 0.777547 0.537604 0.057 Uiso 1 1 calc R . . . .
B012 B 0.4884(12) 0.115(2) 0.4227(4) 0.045(3) Uani 1 1 d . . . . .
C013 C 0.4023(13) -0.136(2) 0.4531(4) 0.055(3) Uani 1 1 d . . . . .
C014 C 0.5966(13) 0.348(3) 0.6957(5) 0.068(5) Uani 1 1 d . . . . .
H014 H 0.635662 0.452349 0.686734 0.082 Uiso 1 1 calc R . . . .
B015 B 0.7840(12) 0.4033(19) 0.5798(4) 0.042(3) Uani 1 1 d . . . . .
C016 C 0.7827(11) 0.345(2) 0.6181(4) 0.054(4) Uani 1 1 d . . . . .
H016 H 0.806842 0.456349 0.631266 0.065 Uiso 1 1 calc R . . . .
C017 C 0.4700(16) 0.213(4) 0.7366(5) 0.078(6) Uani 1 1 d . . . . .
H017 H 0.424531 0.229755 0.755217 0.093 Uiso 1 1 calc R . . . .
C018 C 0.7145(16) 0.496(2) 0.3048(5) 0.072(4) Uani 1 1 d . . . . .
H018 H 0.708329 0.620026 0.313323 0.087 Uiso 1 1 calc R . . . .
C019 C 0.774(2) 0.466(4) 0.2757(6) 0.101(8) Uani 1 1 d . . . . .
H019 H 0.806108 0.568789 0.264368 0.121 Uiso 1 1 calc R . . . .
C01A C 0.5317(18) 0.370(3) 0.7246(5) 0.082(6) Uani 1 1 d . . . . .
H01C H 0.529969 0.487535 0.735630 0.099 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br01 C00N 1.937(14) . ?
Br02 C00U 1.940(14) . ?
O003 C00K 1.367(16) . ?
O003 B015 1.509(17) . ?
O004 C00R 1.319(18) . ?
O004 B012 1.445(18) . ?
O005 C00G 1.472(15) . ?
O005 C00W 1.414(18) . ?
O006 C00F 1.350(18) . ?
O006 B015 1.441(16) . ?
O007 B012 1.501(17) . ?
O007 C013 1.328(18) . ?
O008 C00F 1.203(17) . ?
O009 C00J 1.408(18) . ?
O009 C016 1.460(16) . ?
O00A C00K 1.192(18) . ?
N00B C00M 1.490(18) . ?
N00B C00P 1.500(16) . ?
N00B C00Z 1.484(17) . ?
N00B B012 1.631(17) . ?
O00C C00R 1.204(19) . ?
O00D C013 1.17(2) . ?
N00E C00S 1.494(16) . ?
N00E C00V 1.491(17) . ?
N00E C011 1.524(17) . ?
N00E B015 1.603(17) . ?
C00F C011 1.503(18) . ?
C00G H00H 0.9800 . ?
C00G C00H 1.532(18) . ?
C00G B012 1.58(2) . ?
C00H H00I 0.9700 . ?
C00H H00K 0.9700 . ?
C00H C00U 1.50(2) . ?
C00I C00Q 1.34(2) . ?
C00I C00W 1.51(2) . ?
C00I C018 1.41(2) . ?
C00J H00J 0.9800 . ?
C00J C00N 1.541(19) . ?
C00J C00T 1.49(2) . ?
C00K C00V 1.496(19) . ?
C00L H00L 0.9300 . ?
C00L C00Y 1.34(3) . ?
C00L C019 1.40(3) . ?
C00M H00M 0.9700 . ?
C00M H00O 0.9700 . ?
C00M C013 1.55(2) . ?
C00N H00N 0.9800 . ?
C00N C00O 1.52(2) . ?
C00O H00A 0.9700 . ?
C00O H00B 0.9700 . ?
C00O C016 1.51(2) . ?
C00P H00P 0.9700 . ?
C00P H00Q 0.9700 . ?
C00P C00R 1.50(2) . ?
C00Q H00R 0.9300 . ?
C00Q C00Y 1.40(2) . ?
C00S H00C 0.9600 . ?
C00S H00D 0.9600 . ?
C00S H00E 0.9600 . ?
C00T C00X 1.38(2) . ?
C00T C014 1.41(2) . ?
C00U H00U 0.9800 . ?
C00U C00W 1.52(2) . ?
C00V H00F 0.9700 . ?
C00V H00G 0.9700 . ?
C00W H00W 0.9800 . ?
C00X H00X 0.9300 . ?
C00X C010 1.37(2) . ?
C00Y H00Y 0.9300 . ?
C00Z H00S 0.9600 . ?
C00Z H00T 0.9600 . ?
C00Z H00V 0.9600 . ?
C010 H010 0.9300 . ?
C010 C017 1.34(3) . ?
C011 H01A 0.9700 . ?
C011 H01B 0.9700 . ?
C014 H014 0.9300 . ?
C014 C01A 1.41(3) . ?
B015 C016 1.60(2) . ?
C016 H016 0.9800 . ?
C017 H017 0.9300 . ?
C017 C01A 1.39(3) . ?
C018 H018 0.9300 . ?
C018 C019 1.38(3) . ?
C019 H019 0.9300 . ?
C01A H01C 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00K O003 B015 111.6(10) . . ?
C00R O004 B012 113.1(11) . . ?
C00W O005 C00G 110.2(10) . . ?
C00F O006 B015 111.6(10) . . ?
C013 O007 B012 112.9(11) . . ?
C00J O009 C016 111.4(10) . . ?
C00M N00B C00P 112.0(11) . . ?
C00M N00B B012 104.0(10) . . ?
C00P N00B B012 101.8(9) . . ?
C00Z N00B C00M 109.9(11) . . ?
C00Z N00B C00P 113.5(11) . . ?
C00Z N00B B012 115.2(11) . . ?
C00S N00E C011 109.9(10) . . ?
C00S N00E B015 114.1(10) . . ?
C00V N00E C00S 114.1(10) . . ?
C00V N00E C011 112.0(10) . . ?
C00V N00E B015 105.2(9) . . ?
C011 N00E B015 100.7(9) . . ?
O006 C00F C011 110.5(11) . . ?
O008 C00F O006 122.3(13) . . ?
O008 C00F C011 127.1(15) . . ?
O005 C00G H00H 110.4 . . ?
O005 C00G C00H 103.1(10) . . ?
O005 C00G B012 108.7(10) . . ?
C00H C00G H00H 110.4 . . ?
C00H C00G B012 113.7(11) . . ?
B012 C00G H00H 110.4 . . ?
C00G C00H H00I 111.6 . . ?
C00G C00H H00K 111.6 . . ?
H00I C00H H00K 109.4 . . ?
C00U C00H C00G 101.1(11) . . ?
C00U C00H H00I 111.6 . . ?
C00U C00H H00K 111.6 . . ?
C00Q C00I C00W 123.1(14) . . ?
C00Q C00I C018 118.3(16) . . ?
C018 C00I C00W 118.5(14) . . ?
O009 C00J H00J 108.4 . . ?
O009 C00J C00N 105.1(11) . . ?
O009 C00J C00T 113.4(12) . . ?
C00N C00J H00J 108.4 . . ?
C00T C00J H00J 108.4 . . ?
C00T C00J C00N 113.1(12) . . ?
O003 C00K C00V 111.0(12) . . ?
O00A C00K O003 123.0(13) . . ?
O00A C00K C00V 126.0(13) . . ?
C00Y C00L H00L 119.7 . . ?
C00Y C00L C019 120.6(19) . . ?
C019 C00L H00L 119.7 . . ?
N00B C00M H00M 111.0 . . ?
N00B C00M H00O 111.0 . . ?
N00B C00M C013 103.8(11) . . ?
H00M C00M H00O 109.0 . . ?
C013 C00M H00M 111.0 . . ?
C013 C00M H00O 111.0 . . ?
Br01 C00N H00N 109.2 . . ?
C00J C00N Br01 112.3(10) . . ?
C00J C00N H00N 109.2 . . ?
C00O C00N Br01 114.6(10) . . ?
C00O C00N C00J 102.1(11) . . ?
C00O C00N H00N 109.2 . . ?
C00N C00O H00A 111.4 . . ?
C00N C00O H00B 111.4 . . ?
H00A C00O H00B 109.2 . . ?
C016 C00O C00N 102.1(11) . . ?
C016 C00O H00A 111.4 . . ?
C016 C00O H00B 111.4 . . ?
N00B C00P H00P 110.9 . . ?
N00B C00P H00Q 110.9 . . ?
N00B C00P C00R 104.4(11) . . ?
H00P C00P H00Q 108.9 . . ?
C00R C00P H00P 110.9 . . ?
C00R C00P H00Q 110.9 . . ?
C00I C00Q H00R 118.9 . . ?
C00I C00Q C00Y 122.2(17) . . ?
C00Y C00Q H00R 118.9 . . ?
O004 C00R C00P 111.1(13) . . ?
O00C C00R O004 123.0(14) . . ?
O00C C00R C00P 125.9(14) . . ?
N00E C00S H00C 109.5 . . ?
N00E C00S H00D 109.5 . . ?
N00E C00S H00E 109.5 . . ?
H00C C00S H00D 109.5 . . ?
H00C C00S H00E 109.5 . . ?
H00D C00S H00E 109.5 . . ?
C00X C00T C00J 120.7(14) . . ?
C00X C00T C014 118.6(15) . . ?
C014 C00T C00J 120.7(14) . . ?
Br02 C00U H00U 109.5 . . ?
C00H C00U Br02 113.2(10) . . ?
C00H C00U H00U 109.5 . . ?
C00H C00U C00W 103.3(12) . . ?
C00W C00U Br02 111.9(11) . . ?
C00W C00U H00U 109.5 . . ?
N00E C00V C00K 104.7(10) . . ?
N00E C00V H00F 110.8 . . ?
N00E C00V H00G 110.8 . . ?
C00K C00V H00F 110.8 . . ?
C00K C00V H00G 110.8 . . ?
H00F C00V H00G 108.9 . . ?
O005 C00W C00I 111.3(12) . . ?
O005 C00W C00U 105.9(12) . . ?
O005 C00W H00W 108.7 . . ?
C00I C00W C00U 113.4(13) . . ?
C00I C00W H00W 108.7 . . ?
C00U C00W H00W 108.7 . . ?
C00T C00X H00X 118.7 . . ?
C010 C00X C00T 123(2) . . ?
C010 C00X H00X 118.7 . . ?
C00L C00Y C00Q 120(2) . . ?
C00L C00Y H00Y 120.2 . . ?
C00Q C00Y H00Y 120.2 . . ?
N00B C00Z H00S 109.5 . . ?
N00B C00Z H00T 109.5 . . ?
N00B C00Z H00V 109.5 . . ?
H00S C00Z H00T 109.5 . . ?
H00S C00Z H00V 109.5 . . ?
H00T C00Z H00V 109.5 . . ?
C00X C010 H010 120.5 . . ?
C017 C010 C00X 119(2) . . ?
C017 C010 H010 120.5 . . ?
N00E C011 H01A 110.7 . . ?
N00E C011 H01B 110.7 . . ?
C00F C011 N00E 105.0(11) . . ?
C00F C011 H01A 110.7 . . ?
C00F C011 H01B 110.7 . . ?
H01A C011 H01B 108.8 . . ?
O004 B012 O007 111.6(11) . . ?
O004 B012 N00B 101.3(10) . . ?
O004 B012 C00G 115.0(12) . . ?
O007 B012 N00B 100.8(10) . . ?
O007 B012 C00G 109.8(11) . . ?
C00G B012 N00B 117.3(11) . . ?
O007 C013 C00M 110.7(13) . . ?
O00D C013 O007 125.2(15) . . ?
O00D C013 C00M 124.1(16) . . ?
C00T C014 H014 120.7 . . ?
C01A C014 C00T 118.6(18) . . ?
C01A C014 H014 120.7 . . ?
O003 B015 N00E 100.6(10) . . ?
O003 B015 C016 109.6(11) . . ?
O006 B015 O003 111.4(11) . . ?
O006 B015 N00E 105.1(10) . . ?
O006 B015 C016 111.8(11) . . ?
C016 B015 N00E 117.6(11) . . ?
O009 C016 C00O 103.8(12) . . ?
O009 C016 B015 110.4(11) . . ?
O009 C016 H016 109.1 . . ?
C00O C016 B015 115.2(12) . . ?
C00O C016 H016 109.1 . . ?
B015 C016 H016 109.1 . . ?
C010 C017 H017 119.1 . . ?
C010 C017 C01A 121.7(17) . . ?
C01A C017 H017 119.1 . . ?
C00I C018 H018 119.7 . . ?
C019 C018 C00I 120.5(18) . . ?
C019 C018 H018 119.7 . . ?
C00L C019 H019 120.7 . . ?
C018 C019 C00L 118.7(19) . . ?
C018 C019 H019 120.7 . . ?
C014 C01A H01C 120.3 . . ?
C017 C01A C014 119.3(19) . . ?
C017 C01A H01C 120.3 . . ?

_olex2_date_sample_data_collection 2020-12-29
_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 1.625
_oxdiff_exptl_absorpt_empirical_full_min 0.639
####################################################################### 
# 
# 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_exp_4247
_database_code_depnum_ccdc_archive 'CCDC 2055625'
loop_
_audit_author_name
_audit_author_address
'Manju Rajeswaran'
;Columbia University
United States of America
;
_audit_update_record             
;
2021-01-12 deposited with the CCDC.	2021-03-22 downloaded from the CCDC.
;
_audit_creation_date             2020-12-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H17 B Br N O5'
_chemical_formula_sum            'C11 H17 B Br N O5'
_chemical_formula_weight         333.97
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H17 B1 Br1 N1 O5'
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'
Br Br -0.6763 1.2805 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.7290(10)
_cell_length_b                   12.9542(7)
_cell_length_c                   13.1242(10)
_cell_angle_alpha                90
_cell_angle_beta                 109.149(7)
_cell_angle_gamma                90
_cell_volume                     2847.4(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1955
_cell_measurement_temperature    293.21(10)
_cell_measurement_theta_max      73.0490
_cell_measurement_theta_min      4.3120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5538
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.407
_diffrn_reflns_theta_min         4.315
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.21(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0549
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  38.00   1.00    1.00    --    0.00 -99.00  30.00   35
  2  ω    -65.00 -37.00   1.00    1.00    --    0.00-178.00 -30.00   28
  3  ω    -69.00 -37.00   1.00    1.00    --    0.00-178.00-120.00   32
  4  ω      4.00  33.00   1.00    1.00    --    0.00 -99.00-150.00   29
  5  ω   -135.00 -96.00   1.00    2.55    --  -59.50 -94.00-120.00   39
  6  ω   -124.00 -91.00   1.00    2.55    --  -59.50 -94.00 -60.00   33
  7  ω   -121.00 -84.00   1.00    2.55    --  -59.50 -45.00-150.00   37
  8  ω     37.00 109.00   1.00    2.55    --   59.50  61.00-120.00   72
  9  ω     33.00 117.00   1.00    2.55    --   59.50-125.00  60.00   84
 10  ω      7.00  80.00   1.00    2.55    --   59.50 -61.00  30.00   73
 11  ω    123.00 148.00   1.00    2.55    --  119.00 178.00 -60.00   25
 12  ω    111.00 173.00   1.00    2.55    --  119.00  77.00 120.00   62
 13  ω    120.00 178.00   1.00    2.55    --  119.00  63.00-120.00   58
 14  ω     92.00 143.00   1.00    2.55    --  119.00  50.00 -30.00   51
 15  ω     53.00 112.00   1.00    2.55    --  119.00-111.00  30.00   59
 16  ω     51.00 104.00   1.00    2.55    --  119.00 -99.00 121.00   53
 17  ω    108.00 151.00   1.00    2.55    --  119.00 -77.00-180.00   43
 18  ω    101.00 176.00   1.00    2.55    --  119.00 111.00  30.00   75
 19  ω     47.00  88.00   1.00    2.55    --  119.00 -77.00-180.00   41
 20  ω     82.00 123.00   1.00    2.55    --  119.00 -77.00  90.00   41
 21  ω     46.00  87.00   1.00    2.55    --  119.00-111.00   0.00   41
 22  ω     85.00 176.00   1.00    2.55    --  119.00  77.00 -90.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0301628000
_diffrn_orient_matrix_UB_12      0.1121599000
_diffrn_orient_matrix_UB_13      0.0072685000
_diffrn_orient_matrix_UB_21      0.0111421000
_diffrn_orient_matrix_UB_22      -0.0113723000
_diffrn_orient_matrix_UB_23      -0.1110138000
_diffrn_orient_matrix_UB_31      -0.0861813000
_diffrn_orient_matrix_UB_32      0.0379396000
_diffrn_orient_matrix_UB_33      -0.0552721000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2322
_reflns_number_total             2857
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.589
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2857
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      1.059
_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)+(0.0585P)²+2.7634P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1377
_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 Ternary CH refined with riding coordinates:
 C009(H009), C00D(H00E)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00C(H00C,H00D), C00F(H00I,H00J), C00G(H00K,H00L), C00H(H00M,
 H00N), C00J(H00O,H00P)
2.c Idealised Me refined as rotating group:
 C00E(H00F,H00G,H00H)
;
_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
Br01 Br 0.15071(3) 0.70399(4) 0.51247(4) 0.1020(2) Uani 1 1 d . . . . .
O002 O 0.36201(10) 0.42305(17) 0.76166(15) 0.0552(5) Uani 1 1 d . . . . .
O003 O 0.20373(10) 0.49904(17) 0.64584(16) 0.0555(5) Uani 1 1 d . . . . .
O004 O 0.33492(11) 0.27461(17) 0.64314(18) 0.0615(5) Uani 1 1 d . . . . .
O005 O 0.42983(14) 0.5669(2) 0.8269(2) 0.0791(7) Uani 1 1 d . . . . .
N006 N 0.34368(12) 0.44640(19) 0.57497(17) 0.0504(5) Uani 1 1 d . . . . .
O007 O 0.43083(14) 0.1964(2) 0.5976(2) 0.0858(8) Uani 1 1 d . . . . .
C008 C 0.39144(15) 0.5147(3) 0.7518(2) 0.0568(7) Uani 1 1 d . . . . .
C009 C 0.21773(15) 0.3905(2) 0.6381(2) 0.0542(6) Uani 1 1 d . . . . .
H009 H 0.188542 0.367833 0.564464 0.065 Uiso 1 1 calc R U . . .
C00A C 0.39538(16) 0.2729(3) 0.6043(2) 0.0618(8) Uani 1 1 d . . . . .
C00B C 0.37122(16) 0.5432(2) 0.6341(2) 0.0586(7) Uani 1 1 d . . . . .
H00A H 0.329513 0.595116 0.613714 0.070 Uiso 1 1 calc R U . . .
H00B H 0.417878 0.569635 0.619617 0.070 Uiso 1 1 calc R U . . .
C00C C 0.41137(15) 0.3797(3) 0.5695(2) 0.0600(7) Uani 1 1 d . . . . .
H00C H 0.461824 0.405914 0.617252 0.072 Uiso 1 1 calc R U . . .
H00D H 0.413438 0.378045 0.496559 0.072 Uiso 1 1 calc R U . . .
C00D C 0.12047(15) 0.5226(3) 0.6161(3) 0.0635(8) Uani 1 1 d . . . . .
H00E H 0.093158 0.498501 0.542395 0.076 Uiso 1 1 calc R U . . .
C00E C 0.28517(17) 0.4634(3) 0.4645(2) 0.0662(8) Uani 1 1 d . . . . .
H00F H 0.240298 0.501764 0.469794 0.099 Uiso 1 1 calc R U . . .
H00G H 0.267260 0.397870 0.431066 0.099 Uiso 1 1 calc R U . . .
H00H H 0.310429 0.501312 0.421759 0.099 Uiso 1 1 calc R U . . .
C00F C 0.18658(18) 0.3302(3) 0.7158(3) 0.0677(8) Uani 1 1 d . . . . .
H00I H 0.217044 0.348501 0.789516 0.081 Uiso 1 1 calc R U . . .
H00J H 0.193161 0.256795 0.706771 0.081 Uiso 1 1 calc R U . . .
C00G C 0.08473(18) 0.4692(3) 0.6934(3) 0.0797(11) Uani 1 1 d . . . . .
H00K H 0.109236 0.496357 0.765616 0.096 Uiso 1 1 calc R U . . .
H00L H 0.027909 0.483291 0.671458 0.096 Uiso 1 1 calc R U . . .
C00H C 0.09803(19) 0.3546(4) 0.6941(3) 0.0814(11) Uani 1 1 d . . . . .
H00M H 0.066594 0.325785 0.624973 0.098 Uiso 1 1 calc R U . . .
H00N H 0.080481 0.322942 0.749415 0.098 Uiso 1 1 calc R U . . .
B00I B 0.31033(17) 0.3796(3) 0.6575(2) 0.0499(7) Uani 1 1 d . . . . .
C00J C 0.1137(2) 0.6374(3) 0.6201(3) 0.0805(11) Uani 1 1 d . . . . .
H00O H 0.145071 0.661794 0.691259 0.097 Uiso 1 1 calc R U . . .
H00P H 0.058415 0.656065 0.607737 0.097 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
Br01 C00J 1.944(4) . ?
O002 C008 1.320(4) . ?
O002 B00I 1.484(4) . ?
O003 C009 1.437(4) . ?
O003 C00D 1.431(3) . ?
O004 C00A 1.329(4) . ?
O004 B00I 1.460(4) . ?
O005 C008 1.204(4) . ?
N006 C00B 1.471(4) . ?
N006 C00C 1.500(3) . ?
N006 C00E 1.497(3) . ?
N006 B00I 1.640(4) . ?
O007 C00A 1.192(4) . ?
C008 C00B 1.513(4) . ?
C009 H009 0.9800 . ?
C009 C00F 1.525(4) . ?
C009 B00I 1.583(4) . ?
C00A C00C 1.513(5) . ?
C00B H00A 0.9700 . ?
C00B H00B 0.9700 . ?
C00C H00C 0.9700 . ?
C00C H00D 0.9700 . ?
C00D H00E 0.9800 . ?
C00D C00G 1.527(5) . ?
C00D C00J 1.494(5) . ?
C00E H00F 0.9600 . ?
C00E H00G 0.9600 . ?
C00E H00H 0.9600 . ?
C00F H00I 0.9700 . ?
C00F H00J 0.9700 . ?
C00F C00H 1.534(4) . ?
C00G H00K 0.9700 . ?
C00G H00L 0.9700 . ?
C00G C00H 1.502(6) . ?
C00H H00M 0.9700 . ?
C00H H00N 0.9700 . ?
C00J H00O 0.9700 . ?
C00J H00P 0.9700 . ?

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
C008 O002 B00I 113.3(2) . . ?
C00D O003 C009 112.1(2) . . ?
C00A O004 B00I 112.2(2) . . ?
C00B N006 C00C 112.6(2) . . ?
C00B N006 C00E 113.0(2) . . ?
C00B N006 B00I 103.3(2) . . ?
C00C N006 B00I 101.3(2) . . ?
C00E N006 C00C 110.4(2) . . ?
C00E N006 B00I 115.6(2) . . ?
O002 C008 C00B 110.5(2) . . ?
O005 C008 O002 124.1(3) . . ?
O005 C008 C00B 125.4(3) . . ?
O003 C009 H009 108.4 . . ?
O003 C009 C00F 110.2(2) . . ?
O003 C009 B00I 105.7(2) . . ?
C00F C009 H009 108.4 . . ?
C00F C009 B00I 115.5(2) . . ?
B00I C009 H009 108.4 . . ?
O004 C00A C00C 110.8(2) . . ?
O007 C00A O004 123.6(3) . . ?
O007 C00A C00C 125.6(3) . . ?
N006 C00B C008 104.9(2) . . ?
N006 C00B H00A 110.8 . . ?
N006 C00B H00B 110.8 . . ?
C008 C00B H00A 110.8 . . ?
C008 C00B H00B 110.8 . . ?
H00A C00B H00B 108.8 . . ?
N006 C00C C00A 106.3(2) . . ?
N006 C00C H00C 110.5 . . ?
N006 C00C H00D 110.5 . . ?
C00A C00C H00C 110.5 . . ?
C00A C00C H00D 110.5 . . ?
H00C C00C H00D 108.7 . . ?
O003 C00D H00E 109.4 . . ?
O003 C00D C00G 109.7(3) . . ?
O003 C00D C00J 106.9(3) . . ?
C00G C00D H00E 109.4 . . ?
C00J C00D H00E 109.4 . . ?
C00J C00D C00G 111.9(3) . . ?
N006 C00E H00F 109.5 . . ?
N006 C00E H00G 109.5 . . ?
N006 C00E H00H 109.5 . . ?
H00F C00E H00G 109.5 . . ?
H00F C00E H00H 109.5 . . ?
H00G C00E H00H 109.5 . . ?
C009 C00F H00I 109.6 . . ?
C009 C00F H00J 109.6 . . ?
C009 C00F C00H 110.1(3) . . ?
H00I C00F H00J 108.2 . . ?
C00H C00F H00I 109.6 . . ?
C00H C00F H00J 109.6 . . ?
C00D C00G H00K 109.5 . . ?
C00D C00G H00L 109.5 . . ?
H00K C00G H00L 108.1 . . ?
C00H C00G C00D 110.7(3) . . ?
C00H C00G H00K 109.5 . . ?
C00H C00G H00L 109.5 . . ?
C00F C00H H00M 109.5 . . ?
C00F C00H H00N 109.5 . . ?
C00G C00H C00F 110.7(3) . . ?
C00G C00H H00M 109.5 . . ?
C00G C00H H00N 109.5 . . ?
H00M C00H H00N 108.1 . . ?
O002 B00I N006 99.3(2) . . ?
O002 B00I C009 114.1(2) . . ?
O004 B00I O002 110.6(2) . . ?
O004 B00I N006 102.7(2) . . ?
O004 B00I C009 113.6(2) . . ?
C009 B00I N006 115.2(2) . . ?
Br01 C00J H00O 109.3 . . ?
Br01 C00J H00P 109.3 . . ?
C00D C00J Br01 111.5(2) . . ?
C00D C00J H00O 109.3 . . ?
C00D C00J H00P 109.3 . . ?
H00O C00J H00P 108.0 . . ?

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
O002 C008 C00B N006 -13.9(3) . . . . ?
O003 C009 C00F C00H 55.7(4) . . . . ?
O003 C009 B00I O002 57.1(3) . . . . ?
O003 C009 B00I O004 -174.9(2) . . . . ?
O003 C009 B00I N006 -56.8(3) . . . . ?
O003 C00D C00G C00H -57.1(4) . . . . ?
O003 C00D C00J Br01 64.9(3) . . . . ?
O004 C00A C00C N006 -9.1(3) . . . . ?
O005 C008 C00B N006 165.2(3) . . . . ?
O007 C00A C00C N006 170.2(3) . . . . ?
C008 O002 B00I O004 129.1(2) . . . . ?
C008 O002 B00I N006 21.8(3) . . . . ?
C008 O002 B00I C009 -101.4(3) . . . . ?
C009 O003 C00D C00G 62.3(3) . . . . ?
C009 O003 C00D C00J -176.2(3) . . . . ?
C009 C00F C00H C00G -52.0(4) . . . . ?
C00A O004 B00I O002 -83.1(3) . . . . ?
C00A O004 B00I N006 22.1(3) . . . . ?
C00A O004 B00I C009 147.2(2) . . . . ?
C00B N006 C00C C00A 130.5(2) . . . . ?
C00B N006 B00I O002 -28.5(2) . . . . ?
C00B N006 B00I O004 -142.2(2) . . . . ?
C00B N006 B00I C009 93.8(3) . . . . ?
C00C N006 C00B C008 -82.6(3) . . . . ?
C00C N006 B00I O002 88.2(2) . . . . ?
C00C N006 B00I O004 -25.5(3) . . . . ?
C00C N006 B00I C009 -149.5(3) . . . . ?
C00D O003 C009 C00F -62.2(3) . . . . ?
C00D O003 C009 B00I 172.3(2) . . . . ?
C00D C00G C00H C00F 52.7(4) . . . . ?
C00E N006 C00B C008 151.5(2) . . . . ?
C00E N006 C00C C00A -102.2(3) . . . . ?
C00E N006 B00I O002 -152.5(2) . . . . ?
C00E N006 B00I O004 93.8(3) . . . . ?
C00E N006 B00I C009 -30.2(4) . . . . ?
C00F C009 B00I O002 -65.0(4) . . . . ?
C00F C009 B00I O004 63.0(3) . . . . ?
C00F C009 B00I N006 -178.9(3) . . . . ?
C00G C00D C00J Br01 -174.9(2) . . . . ?
B00I O002 C008 O005 174.3(3) . . . . ?
B00I O002 C008 C00B -6.6(3) . . . . ?
B00I O004 C00A O007 171.3(3) . . . . ?
B00I O004 C00A C00C -9.4(3) . . . . ?
B00I N006 C00B C008 25.9(2) . . . . ?
B00I N006 C00C C00A 20.7(3) . . . . ?
B00I C009 C00F C00H 175.3(3) . . . . ?
C00J C00D C00G C00H -175.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.317
_oxdiff_exptl_absorpt_empirical_full_min 0.830
