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

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

data_SB-LNE-7-6Br_a
_database_code_depnum_ccdc_archive 'CCDC 2283724'
loop_
_audit_author_name
_audit_author_address
'Subhankar Biswas'
;IIT Guwahati
India
;
_audit_update_record             
;
2023-07-22 deposited with the CCDC.	2023-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H18 Br N3 O3'
_chemical_formula_weight         464.31

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.1820(6)
_cell_length_b                   10.2729(6)
_cell_length_c                   19.3413(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2023.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9807
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      25.09

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    2.063
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5507
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   
;
 SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
 --------------------------------------------------------------------------

 Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48721
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.106
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3531
_reflns_number_gt                3323
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.994

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0350P)²+0.3910P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1355 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.040(3)
_chemical_absolute_configuration R,S
_refine_ls_number_reflns         3531
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0604
_refine_ls_wR_factor_gt          0.0585
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.09898(4) 0.70320(3) 0.44257(2) 0.05703(13) Uani 1 1 d . . . . .
O002 O 0.2869(2) 0.2776(2) 0.12586(13) 0.0590(6) Uani 1 1 d . . . . .
O003 O 0.1778(2) 0.0975(2) 0.22722(11) 0.0477(5) Uani 1 1 d . . . . .
N004 N 0.1201(2) 0.2985(2) 0.27036(12) 0.0384(5) Uani 1 1 d . . . . .
N005 N 0.3776(2) 0.1130(2) 0.33577(13) 0.0393(5) Uani 1 1 d . . . . .
O1 O 0.3686(3) 0.1036(3) 0.08102(13) 0.0772(8) Uani 1 1 d . . . . .
N1 N 0.3623(3) 0.1856(3) 0.12665(14) 0.0515(7) Uani 1 1 d . . . . .
C008 C 0.3326(3) 0.2264(3) 0.29738(15) 0.0375(6) Uani 1 1 d . . . . .
C009 C 0.5728(3) 0.2740(3) 0.28152(17) 0.0441(7) Uani 1 1 d . . . . .
H009 H 0.633473 0.336080 0.267279 0.053 Uiso 1 1 calc R U . . .
C00A C 0.3022(3) 0.0224(3) 0.36947(18) 0.0459(7) Uani 1 1 d . . . . .
H00A H 0.212594 0.009563 0.363240 0.055 Uiso 1 1 calc R U . . .
C00B C 0.2946(3) 0.3415(3) 0.34155(15) 0.0359(6) Uani 1 1 d . . . . .
C00C C 0.2018(3) 0.1956(3) 0.26006(14) 0.0385(6) Uani 1 1 d . . . . .
C00D C 0.1096(3) 0.4915(3) 0.34824(14) 0.0397(6) Uani 1 1 d . . . . .
H00D H 0.028139 0.520212 0.332680 0.048 Uiso 1 1 calc R U . . .
C00E C 0.5052(3) 0.1046(3) 0.36033(16) 0.0380(6) Uani 1 1 d . . . . .
C00F C 0.6040(3) 0.1943(3) 0.33379(15) 0.0394(6) Uani 1 1 d . . . . .
C00G C 0.1772(3) 0.5547(3) 0.40088(15) 0.0404(7) Uani 1 1 d . . . . .
C00H C 0.4413(3) 0.2658(3) 0.24483(16) 0.0412(7) Uani 1 1 d . . . . .
H00H H 0.419996 0.351973 0.226178 0.049 Uiso 1 1 calc R U . . .
C00I C 0.3573(3) 0.4048(3) 0.39462(16) 0.0441(7) Uani 1 1 d . . . . .
H00I H 0.438590 0.375899 0.410251 0.053 Uiso 1 1 calc R U . . .
C00J C 0.7341(3) 0.1942(3) 0.36897(16) 0.0413(6) Uani 1 1 d . . . . .
C00K C 0.2975(3) 0.5134(3) 0.42495(16) 0.0469(8) Uani 1 1 d . . . . .
H00K H 0.338656 0.557196 0.461016 0.056 Uiso 1 1 calc R U . . .
C00L C 0.1706(3) 0.3839(3) 0.32053(14) 0.0362(6) Uani 1 1 d . . . . .
C00M C 0.3805(3) -0.0452(3) 0.41342(17) 0.0498(8) Uani 1 1 d . . . . .
H00M H 0.354448 -0.113508 0.441834 0.060 Uiso 1 1 calc R U . . .
C00N C 0.5081(3) 0.0066(3) 0.40834(19) 0.0449(7) Uani 1 1 d . . . . .
H00N H 0.581297 -0.020784 0.433143 0.054 Uiso 1 1 calc R U . . .
C00O C 0.8124(3) 0.0839(3) 0.3686(2) 0.0517(8) Uani 1 1 d . . . . .
H00O H 0.784180 0.009705 0.345369 0.062 Uiso 1 1 calc R U . . .
C00P C 0.4587(3) 0.1717(3) 0.18464(17) 0.0487(8) Uani 1 1 d . . . . .
H00B H 0.546405 0.182907 0.166044 0.058 Uiso 1 1 calc R U . . .
H00C H 0.452798 0.083549 0.202418 0.058 Uiso 1 1 calc R U . . .
C00Q C -0.0113(3) 0.3065(4) 0.24116(17) 0.0503(8) Uani 1 1 d . . . . .
H00E H -0.012391 0.264974 0.196688 0.075 Uiso 1 1 calc R U . . .
H00F H -0.035915 0.396190 0.236173 0.075 Uiso 1 1 calc R U . . .
H00G H -0.072361 0.263526 0.271336 0.075 Uiso 1 1 calc R U . . .
C00R C 0.9317(3) 0.0832(4) 0.4022(2) 0.0647(10) Uani 1 1 d . . . . .
H00R H 0.982817 0.008161 0.401884 0.078 Uiso 1 1 calc R U . . .
C00S C 0.7784(3) 0.3034(4) 0.40401(18) 0.0542(8) Uani 1 1 d . . . . .
H00S H 0.727265 0.378421 0.404967 0.065 Uiso 1 1 calc R U . . .
C00T C 0.9757(3) 0.1912(5) 0.43600(19) 0.0690(11) Uani 1 1 d . . . . .
H00T H 1.057171 0.190629 0.457773 0.083 Uiso 1 1 calc R U . . .
C00U C 0.8984(4) 0.3013(5) 0.43757(19) 0.0708(11) Uani 1 1 d . . . . .
H00U H 0.927049 0.374711 0.461343 0.085 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 C00G 1.901(3) . ?
O002 N1 1.217(3) . ?
O003 C00C 1.216(4) . ?
N004 C00C 1.360(4) . ?
N004 C00L 1.406(4) . ?
N004 C00Q 1.454(4) . ?
N005 C00A 1.371(4) . ?
N005 C00E 1.386(4) . ?
N005 C008 1.456(4) . ?
O1 N1 1.222(4) . ?
N1 C00P 1.497(4) . ?
C008 C00B 1.509(4) . ?
C008 C00C 1.548(4) . ?
C008 C00H 1.556(4) . ?
C009 C00F 1.339(4) . ?
C009 C00H 1.518(4) . ?
C00A C00M 1.356(5) . ?
C00B C00I 1.372(4) . ?
C00B C00L 1.396(4) . ?
C00D C00L 1.377(4) . ?
C00D C00G 1.390(4) . ?
C00E C00N 1.369(4) . ?
C00E C00F 1.458(4) . ?
C00F C00J 1.489(4) . ?
C00G C00K 1.378(5) . ?
C00H C00P 1.524(4) . ?
C00I C00K 1.399(5) . ?
C00J C00O 1.385(4) . ?
C00J C00S 1.386(5) . ?
C00M C00N 1.408(5) . ?
C00O C00R 1.379(5) . ?
C00R C00T 1.363(6) . ?
C00S C00U 1.383(5) . ?
C00T C00U 1.379(6) . ?

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
C00C N004 C00L 111.2(2) . . ?
C00C N004 C00Q 123.4(3) . . ?
C00L N004 C00Q 124.7(2) . . ?
C00A N005 C00E 108.6(2) . . ?
C00A N005 C008 127.5(2) . . ?
C00E N005 C008 121.4(2) . . ?
O002 N1 O1 124.0(3) . . ?
O002 N1 C00P 119.8(3) . . ?
O1 N1 C00P 116.1(3) . . ?
N005 C008 C00B 114.8(2) . . ?
N005 C008 C00C 110.2(2) . . ?
C00B C008 C00C 101.8(2) . . ?
N005 C008 C00H 108.5(2) . . ?
C00B C008 C00H 110.4(2) . . ?
C00C C008 C00H 111.2(2) . . ?
C00F C009 C00H 121.9(3) . . ?
C00M C00A N005 108.4(3) . . ?
C00I C00B C00L 119.4(3) . . ?
C00I C00B C008 132.5(3) . . ?
C00L C00B C008 108.1(2) . . ?
O003 C00C N004 126.8(3) . . ?
O003 C00C C008 125.9(3) . . ?
N004 C00C C008 107.4(2) . . ?
C00L C00D C00G 115.9(3) . . ?
C00N C00E N005 107.4(3) . . ?
C00N C00E C00F 133.5(3) . . ?
N005 C00E C00F 119.1(3) . . ?
C009 C00F C00E 119.3(3) . . ?
C009 C00F C00J 123.8(3) . . ?
C00E C00F C00J 116.9(3) . . ?
C00K C00G C00D 123.0(3) . . ?
C00K C00G Br01 118.5(2) . . ?
C00D C00G Br01 118.6(2) . . ?
C009 C00H C00P 106.8(2) . . ?
C009 C00H C008 109.7(2) . . ?
C00P C00H C008 114.6(2) . . ?
C00B C00I C00K 119.3(3) . . ?
C00O C00J C00S 118.5(3) . . ?
C00O C00J C00F 120.7(3) . . ?
C00S C00J C00F 120.8(3) . . ?
C00G C00K C00I 119.4(3) . . ?
C00D C00L C00B 123.0(3) . . ?
C00D C00L N004 127.2(3) . . ?
C00B C00L N004 109.7(2) . . ?
C00A C00M C00N 107.7(3) . . ?
C00E C00N C00M 107.8(3) . . ?
C00R C00O C00J 120.6(3) . . ?
N1 C00P C00H 115.8(3) . . ?
C00T C00R C00O 120.8(4) . . ?
C00U C00S C00J 120.3(4) . . ?
C00R C00T C00U 119.4(3) . . ?
C00T C00U C00S 120.5(4) . . ?

_refine_diff_density_max         0.296
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.032



####################################################################### 
# 
# 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_LNE_APNBS_mono_Br
_database_code_depnum_ccdc_archive 'CCDC 2283725'
loop_
_audit_author_name
_audit_author_address
'SUBHANKAR BISWAS'
;IIT GUWAHATI
India
;
_audit_update_record             
;
2023-07-22 deposited with the CCDC.	2023-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H18 Br N3 O3'
_chemical_formula_weight         464.31

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.7574(7)
_cell_length_b                   13.9180(14)
_cell_length_c                   9.8197(9)
_cell_angle_alpha                90
_cell_angle_beta                 107.102(3)
_cell_angle_gamma                90
_cell_volume                     1013.33(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    6939
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      27.56

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_absorpt_coefficient_mu    2.059
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5727
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
 --------------------------------------------------------------------------

 Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9275
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.617
_diffrn_reflns_theta_max         24.493
_diffrn_reflns_theta_full        24.493
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             3224
_reflns_number_gt                3025
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_max     0.917
_reflns_Friedel_fraction_full    0.917

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0304P)²+0.8063P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1300 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.040(5)
_chemical_absolute_configuration R,S
_refine_ls_number_reflns         3224
_refine_ls_number_parameters     272
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0570
_refine_ls_wR_factor_gt          0.0554
_refine_ls_goodness_of_fit_ref   0.709
_refine_ls_restrained_S_all      0.708
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000

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 0.80630(5) 0.37079(3) 0.77000(4) 0.05584(15) Uani 1 1 d . . . . .
O002 O 0.0342(3) 0.4568(2) 0.4685(3) 0.0510(7) Uani 1 1 d . . . . .
N003 N 0.3503(4) 0.5887(2) 0.5595(3) 0.0319(6) Uani 1 1 d . . . . .
N004 N 0.1506(4) 0.4313(2) 0.2819(3) 0.0365(7) Uani 1 1 d . . . . .
C005 C 0.5903(5) 0.5366(3) 0.3535(4) 0.0388(9) Uani 1 1 d . . . . .
H005 H 0.670736 0.567381 0.430352 0.047 Uiso 1 1 calc R U . . .
C006 C 0.6271(5) 0.4636(2) 0.6889(4) 0.0325(8) Uani 1 1 d . . . . .
C007 C 0.4287(5) 0.5012(2) 0.3640(4) 0.0306(7) Uani 1 1 d . . . . .
C008 C 0.4777(6) 0.7186(3) 0.6783(5) 0.0399(10) Uani 1 1 d . . . . .
H008 H 0.558225 0.759672 0.740281 0.048 Uiso 1 1 calc R U . . .
C009 C 0.8387(5) 0.6283(3) 0.9503(4) 0.0390(9) Uani 1 1 d . . . . .
H009 H 0.735971 0.630858 0.980700 0.047 Uiso 1 1 calc R U . . .
C00A C 0.3077(6) 0.7436(3) 0.5877(4) 0.0454(10) Uani 1 1 d . . . . .
H00A H 0.255175 0.804154 0.579629 0.055 Uiso 1 1 calc R U . . .
C00B C 0.4509(4) 0.4216(2) 0.5990(3) 0.0300(8) Uani 1 1 d . . . . .
H00B H 0.478243 0.366084 0.547461 0.036 Uiso 1 1 calc R U . . .
O1 O 0.2287(5) 0.2628(2) 0.5315(5) 0.0758(10) Uani 1 1 d . . . . .
C00D C 0.6521(5) 0.5573(2) 0.7202(3) 0.0294(7) Uani 1 1 d . . . . .
C00E C 0.2334(5) 0.6644(3) 0.5142(4) 0.0407(9) Uani 1 1 d . . . . .
H00E H 0.122128 0.661469 0.444820 0.049 Uiso 1 1 calc R U . . .
C00F C 0.1558(5) 0.4609(3) 0.4145(4) 0.0364(8) Uani 1 1 d . . . . .
C00G C 1.0031(6) 0.6572(3) 1.0411(4) 0.0435(9) Uani 1 1 d . . . . .
H00G H 1.010693 0.677786 1.132769 0.052 Uiso 1 1 calc R U . . .
N1 N 0.2429(5) 0.2947(3) 0.6497(5) 0.0547(9) Uani 1 1 d . . . . .
C00I C 0.3473(5) 0.3857(3) 0.6994(4) 0.0456(10) Uani 1 1 d . . . . .
H00C H 0.431907 0.374690 0.792729 0.055 Uiso 1 1 calc R U . . .
H00D H 0.264156 0.435483 0.709252 0.055 Uiso 1 1 calc R U . . .
C00J C 0.6302(6) 0.5253(3) 0.2255(4) 0.0473(10) Uani 1 1 d . . . . .
H00J H 0.737727 0.549421 0.215731 0.057 Uiso 1 1 calc R U . . .
C00K C 0.9794(5) 0.5962(3) 0.7691(4) 0.0403(9) Uani 1 1 d . . . . .
H00K H 0.971972 0.576438 0.677088 0.048 Uiso 1 1 calc R U . . .
C00L C 0.3499(5) 0.4975(2) 0.4872(4) 0.0306(7) Uani 1 1 d . . . . .
C00M C 0.5043(5) 0.6222(2) 0.6591(4) 0.0313(7) Uani 1 1 d . . . . .
C00N C 0.3093(5) 0.4563(3) 0.2481(4) 0.0337(8) Uani 1 1 d . . . . .
C00O C -0.0004(5) 0.3803(4) 0.1867(4) 0.0548(10) Uani 1 1 d . . . . .
H00F H 0.038036 0.317521 0.167537 0.082 Uiso 1 1 calc R U . . .
H00H H -0.043683 0.415343 0.098992 0.082 Uiso 1 1 calc R U . . .
H00I H -0.095324 0.374458 0.230551 0.082 Uiso 1 1 calc R U . . .
C00P C 0.8262(5) 0.5958(2) 0.8147(4) 0.0318(7) Uani 1 1 d . . . . .
C00Q C 1.1551(6) 0.6555(3) 0.9967(5) 0.0447(10) Uani 1 1 d . . . . .
H00Q H 1.265798 0.674297 1.058154 0.054 Uiso 1 1 calc R U . . .
O00R O 0.1773(6) 0.2576(3) 0.7335(5) 0.0992(15) Uani 1 1 d . . . . .
C00S C 0.3473(6) 0.4429(3) 0.1212(4) 0.0436(9) Uani 1 1 d . . . . .
H00S H 0.267252 0.411619 0.044713 0.052 Uiso 1 1 calc R U . . .
C00T C 1.1424(5) 0.6257(3) 0.8597(5) 0.0463(10) Uani 1 1 d . . . . .
H00T H 1.244627 0.625654 0.828532 0.056 Uiso 1 1 calc R U . . .
C00U C 0.5117(6) 0.4785(3) 0.1132(4) 0.0512(10) Uani 1 1 d . . . . .
H00U H 0.542309 0.470454 0.029152 0.061 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 C006 1.893(3) . ?
O002 C00F 1.213(4) . ?
N003 C00E 1.375(5) . ?
N003 C00M 1.383(5) . ?
N003 C00L 1.454(4) . ?
N004 C00F 1.355(5) . ?
N004 C00N 1.410(5) . ?
N004 C00O 1.450(5) . ?
C005 C007 1.379(5) . ?
C005 C00J 1.389(6) . ?
C006 C00D 1.342(5) . ?
C006 C00B 1.510(5) . ?
C007 C00N 1.387(5) . ?
C007 C00L 1.509(5) . ?
C008 C00M 1.379(5) . ?
C008 C00A 1.400(6) . ?
C009 C00P 1.383(5) . ?
C009 C00G 1.383(6) . ?
C00A C00E 1.350(6) . ?
C00B C00I 1.528(5) . ?
C00B C00L 1.559(5) . ?
O1 N1 1.217(5) . ?
C00D C00M 1.444(5) . ?
C00D C00P 1.495(5) . ?
C00F C00L 1.550(5) . ?
C00G C00Q 1.373(6) . ?
N1 O00R 1.204(5) . ?
N1 C00I 1.506(6) . ?
C00J C00U 1.374(6) . ?
C00K C00T 1.378(5) . ?
C00K C00P 1.387(5) . ?
C00N C00S 1.374(5) . ?
C00Q C00T 1.383(6) . ?
C00S C00U 1.392(6) . ?

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
C00E N003 C00M 108.8(3) . . ?
C00E N003 C00L 127.1(3) . . ?
C00M N003 C00L 121.1(3) . . ?
C00F N004 C00N 111.7(3) . . ?
C00F N004 C00O 123.9(3) . . ?
C00N N004 C00O 124.4(3) . . ?
C007 C005 C00J 118.4(4) . . ?
C00D C006 C00B 123.8(3) . . ?
C00D C006 Br01 121.9(3) . . ?
C00B C006 Br01 114.1(2) . . ?
C00N C007 C005 120.2(3) . . ?
C00N C007 C00L 108.2(3) . . ?
C005 C007 C00L 131.6(3) . . ?
C00M C008 C00A 107.8(4) . . ?
C00P C009 C00G 120.4(4) . . ?
C00E C00A C008 108.1(4) . . ?
C006 C00B C00I 107.9(3) . . ?
C006 C00B C00L 109.3(3) . . ?
C00I C00B C00L 115.1(3) . . ?
C006 C00D C00M 118.0(3) . . ?
C006 C00D C00P 122.3(3) . . ?
C00M C00D C00P 119.7(3) . . ?
C00A C00E N003 108.3(4) . . ?
O002 C00F N004 126.8(3) . . ?
O002 C00F C00L 126.1(3) . . ?
N004 C00F C00L 107.1(3) . . ?
C00Q C00G C009 120.4(4) . . ?
O00R N1 O1 123.9(4) . . ?
O00R N1 C00I 115.7(4) . . ?
O1 N1 C00I 120.3(3) . . ?
N1 C00I C00B 113.6(3) . . ?
C00U C00J C005 120.4(4) . . ?
C00T C00K C00P 120.2(3) . . ?
N003 C00L C007 114.8(3) . . ?
N003 C00L C00F 112.0(3) . . ?
C007 C00L C00F 102.1(3) . . ?
N003 C00L C00B 108.7(3) . . ?
C007 C00L C00B 110.5(3) . . ?
C00F C00L C00B 108.7(3) . . ?
C008 C00M N003 106.9(3) . . ?
C008 C00M C00D 133.2(3) . . ?
N003 C00M C00D 119.9(3) . . ?
C00S C00N C007 122.4(3) . . ?
C00S C00N N004 127.9(3) . . ?
C007 C00N N004 109.7(3) . . ?
C009 C00P C00K 119.0(3) . . ?
C009 C00P C00D 120.6(3) . . ?
C00K C00P C00D 120.3(3) . . ?
C00G C00Q C00T 119.5(4) . . ?
C00N C00S C00U 116.5(4) . . ?
C00K C00T C00Q 120.4(4) . . ?
C00J C00U C00S 122.1(4) . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.033



