# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_KV_a
_database_code_depnum_ccdc_archive 'CCDC 2387375'
loop_
_audit_author_name
_audit_author_address
'Alex P. Andrews'
;IISER Thiruvananthapuram
India
;
_audit_update_record             
;
2024-09-27 deposited with the CCDC.	2024-11-08 downloaded from the CCDC.
;
_audit_creation_date             2024-09-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_chemical_formula_moiety         'C13 H13 Br2 N O4'
_chemical_formula_sum            'C13 H13 Br2 N O4'
_chemical_formula_weight         407.059
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
Br -0.38188 2.46625 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95570 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   4.331(2)
_cell_length_b                   13.766(6)
_cell_length_c                   25.014(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.814(6)
_cell_angle_gamma                90
_cell_volume                     1490.6(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2364
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.46
_cell_measurement_theta_min      2.20
_exptl_absorpt_coefficient_mu    5.449
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4240
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1468 before and 0.0516 after correction.
The Ratio of minimum to maximum transmission is 0.5686.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.814
_exptl_crystal_description       needle
_exptl_crystal_F_000             798.877
_exptl_crystal_size_max          0.085
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.035
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_Laue_measured_fraction_full 0.9985
_diffrn_reflns_Laue_measured_fraction_max 0.9905
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            20274
_diffrn_reflns_point_group_measured_fraction_full 0.9985
_diffrn_reflns_point_group_measured_fraction_max 0.9905
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.51
_diffrn_reflns_theta_min         2.20
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9985
_diffrn_measured_fraction_theta_max 0.9905
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              5
_reflns_limit_h_min              -5
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              33
_reflns_limit_l_min              0
_reflns_number_gt                2074
_reflns_number_total             3752
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         1.0870
_refine_diff_density_min         -1.1824
_refine_diff_density_rms         0.2638
_refine_ls_d_res_high            0.7444
_refine_ls_d_res_low             9.2544
_refine_ls_goodness_of_fit_ref   1.0301
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    19
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3752
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1225
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.0301
_refine_ls_shift/su_max          -0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0259P)²+2.3310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.1026
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00H(H00a,H00b)
2.b Aromatic/amide H refined with riding coordinates:
 N007(H007), C00D(H00D)
2.c Idealised Me refined as rotating group:
 C00I(H00c,H00e,H00f), C00J(H00g,H00h,H00i), C00K(H00j,H00k,H00l)
;
_atom_sites_solution_primary     iterative
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
Br01 Br 0.63334(13) 0.63979(4) 0.35491(2) 0.05144(18) Uani 1.000000 .
Br02 Br 0.31704(14) 0.16311(4) 0.42019(2) 0.05626(19) Uani 1.000000 .
O003 O 0.2169(8) 0.5769(2) 0.25957(13) 0.0467(9) Uani 1.000000 .
O004 O 0.7440(8) 0.2360(2) 0.51506(14) 0.0504(9) Uani 1.000000 .
O005 O -0.0328(8) 0.4038(2) 0.23783(15) 0.0570(10) Uani 1.000000 .
O006 O 0.9581(9) 0.3850(3) 0.52247(15) 0.0616(11) Uani 1.000000 .
N007 N 0.6472(9) 0.4402(3) 0.42725(16) 0.0436(10) Uani 1.000000 .
H007 H 0.7492(9) 0.4875(3) 0.44173(16) 0.0524(12) Uiso 1.000000 R
C008 C 0.4427(10) 0.5186(3) 0.3416(2) 0.0386(11) Uani 1.000000 .
C009 C 0.4368(11) 0.2931(3) 0.41409(19) 0.0409(12) Uani 1.000000 .
C00A C 0.4815(10) 0.4443(3) 0.3792(2) 0.0388(11) Uani 1.000000 .
C00B C 0.2699(11) 0.5019(3) 0.29519(19) 0.0397(12) Uani 1.000000 .
C00C C 0.6223(11) 0.3482(3) 0.4482(2) 0.0406(12) Uani 1.000000 .
C00D C 0.1664(11) 0.3354(3) 0.3226(2) 0.0440(12) Uani 1.000000 .
H00D H 0.0739(11) 0.2753(3) 0.3164(2) 0.0528(15) Uiso 1.000000 R
C00E C 0.1313(11) 0.4094(3) 0.2859(2) 0.0415(12) Uani 1.000000 .
C00F C 0.3457(11) 0.3527(3) 0.3697(2) 0.0422(12) Uani 1.000000 .
C00G C 0.7924(12) 0.3271(4) 0.4987(2) 0.0451(13) Uani 1.000000 .
C00H C 0.9289(13) 0.2019(4) 0.5608(2) 0.0539(15) Uani 1.000000 .
H00a H 1.1468(13) 0.2103(4) 0.5543(2) 0.0646(17) Uiso 1.000000 R
H00b H 0.8795(13) 0.2388(4) 0.5925(2) 0.0646(17) Uiso 1.000000 R
C00I C -0.1817(13) 0.3143(4) 0.2251(2) 0.0581(15) Uani 1.000000 .
H00c H -0.295(7) 0.3205(9) 0.1917(8) 0.087(2) Uiso 1.000000 GR
H00e H -0.0295(15) 0.2641(7) 0.2223(14) 0.087(2) Uiso 1.000000 GR
H00f H -0.321(6) 0.2980(14) 0.2529(8) 0.087(2) Uiso 1.000000 GR
C00J C 0.3896(14) 0.5724(4) 0.2112(2) 0.0672(17) Uani 1.000000 .
H00g H 0.310(6) 0.619(2) 0.1861(6) 0.101(3) Uiso 1.000000 GR
H00h H 0.603(2) 0.586(3) 0.2195(3) 0.101(3) Uiso 1.000000 GR
H00i H 0.371(8) 0.5086(10) 0.1959(9) 0.101(3) Uiso 1.000000 GR
C00K C 0.8578(17) 0.0968(4) 0.5689(3) 0.087(2) Uani 1.000000 .
H00j H 0.913(10) 0.0607(6) 0.5378(8) 0.130(3) Uiso 1.000000 GR
H00k H 0.974(9) 0.0731(10) 0.5996(12) 0.130(3) Uiso 1.000000 GR
H00l H 0.641(3) 0.0892(6) 0.5746(19) 0.130(3) Uiso 1.000000 GR


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 C008 1.887(5) . ?
Br02 C009 1.871(5) . ?
O003 C00B 1.378(5) . ?
O003 C00J 1.443(6) . ?
O004 C00G 1.338(6) . ?
O004 C00H 1.454(6) . ?
O005 C00E 1.379(6) . ?
O005 C00I 1.422(6) . ?
O006 C00G 1.214(6) . ?
N007 H007 0.8600 . ?
N007 C00A 1.381(6) . ?
N007 C00C 1.376(6) . ?
C008 C00A 1.396(6) . ?
C008 C00B 1.380(6) . ?
C009 C00C 1.380(7) . ?
C009 C00F 1.427(7) . ?
C00A C00F 1.408(6) . ?
C00B C00E 1.424(6) . ?
C00C C00G 1.473(7) . ?
C00D H00D 0.9300 . ?
C00D C00E 1.376(7) . ?
C00D C00F 1.411(7) . ?
C00H H00a 0.9700 . ?
C00H H00b 0.9700 . ?
C00H C00K 1.494(7) . ?
C00I H00c 0.9600 . ?
C00I H00e 0.9600 . ?
C00I H00f 0.9600 . ?
C00J H00g 0.9600 . ?
C00J H00h 0.9600 . ?
C00J H00i 0.9600 . ?
C00K H00j 0.9600 . ?
C00K H00k 0.9600 . ?
C00K H00l 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00J O003 C00B 115.4(4) . . ?
C00H O004 C00G 117.1(4) . . ?
C00I O005 C00E 117.4(4) . . ?
C00A N007 H007 125.6(3) . . ?
C00C N007 H007 125.6(3) . . ?
C00C N007 C00A 108.8(4) . . ?
C00A C008 Br01 119.1(4) . . ?
C00B C008 Br01 121.2(4) . . ?
C00B C008 C00A 119.7(4) . . ?
C00C C009 Br02 129.3(4) . . ?
C00F C009 Br02 122.9(4) . . ?
C00F C009 C00C 107.8(4) . . ?
C008 C00A N007 131.6(4) . . ?
C00F C00A N007 108.3(4) . . ?
C00F C00A C008 120.0(5) . . ?
C008 C00B O003 119.6(4) . . ?
C00E C00B O003 120.2(4) . . ?
C00E C00B C008 120.1(4) . . ?
C009 C00C N007 108.8(4) . . ?
C00G C00C N007 117.7(4) . . ?
C00G C00C C009 133.4(4) . . ?
C00E C00D H00D 120.7(3) . . ?
C00F C00D H00D 120.7(3) . . ?
C00F C00D C00E 118.6(4) . . ?
C00B C00E O005 113.3(4) . . ?
C00D C00E O005 125.6(4) . . ?
C00D C00E C00B 121.0(5) . . ?
C00A C00F C009 106.2(4) . . ?
C00D C00F C009 133.2(5) . . ?
C00D C00F C00A 120.6(5) . . ?
O006 C00G O004 124.2(5) . . ?
C00C C00G O004 111.6(4) . . ?
C00C C00G O006 124.2(5) . . ?
H00a C00H O004 110.1(3) . . ?
H00b C00H O004 110.1(3) . . ?
H00b C00H H00a 108.4 . . ?
C00K C00H O004 108.0(5) . . ?
C00K C00H H00a 110.1(4) . . ?
C00K C00H H00b 110.1(4) . . ?
H00c C00I O005 109.5 . . ?
H00e C00I O005 109.5 . . ?
H00e C00I H00c 109.5 . . ?
H00f C00I O005 109.5 . . ?
H00f C00I H00c 109.5 . . ?
H00f C00I H00e 109.5 . . ?
H00g C00J O003 109.5 . . ?
H00h C00J O003 109.5 . . ?
H00h C00J H00g 109.5 . . ?
H00i C00J O003 109.5 . . ?
H00i C00J H00g 109.5 . . ?
H00i C00J H00h 109.5 . . ?
H00j C00K C00H 109.5 . . ?
H00k C00K C00H 109.5 . . ?
H00k C00K H00j 109.5 . . ?
H00l C00K C00H 109.5 . . ?
H00l C00K H00j 109.5 . . ?
H00l C00K H00k 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br01 C008 C00A N007 -1.4(5) . . . . ?
Br01 C008 C00A C00F -179.0(3) . . . . ?
Br01 C008 C00B O003 -4.6(4) . . . . ?
Br01 C008 C00B C00E 179.3(4) . . . . ?
Br02 C009 C00C N007 179.8(5) . . . . ?
Br02 C009 C00C C00G 1.4(6) . . . . ?
Br02 C009 C00F C00A -179.5(4) . . . . ?
Br02 C009 C00F C00D -1.0(5) . . . . ?
O003 C00B C008 C00A 176.3(4) . . . . ?
O003 C00B C00E O005 4.1(5) . . . . ?
O003 C00B C00E C00D -176.0(4) . . . . ?
O004 C00G C00C N007 178.9(4) . . . . ?
O004 C00G C00C C009 -2.8(6) . . . . ?
O005 C00E C00B C008 -179.8(4) . . . . ?
O005 C00E C00D C00F 179.2(5) . . . . ?
O006 C00G C00C N007 -1.7(6) . . . . ?
O006 C00G C00C C009 176.7(5) . . . . ?
N007 C00A C008 C00B 177.8(5) . . . . ?
N007 C00A C00F C009 -0.1(4) . . . . ?
N007 C00A C00F C00D -178.8(4) . . . . ?
N007 C00C C009 C00F 0.9(4) . . . . ?
C008 C00A C00F C009 178.0(5) . . . . ?
C008 C00A C00F C00D -0.8(5) . . . . ?
C008 C00B C00E C00D 0.0(5) . . . . ?
C009 C00F C00D C00E -177.4(6) . . . . ?
C00A C00F C00D C00E 1.0(5) . . . . ?
C00B C00E C00D C00F -0.6(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        DMICE-Br2
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate/hexane mixture'
####################################################################### 
# 
# 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_dmicebm
_database_code_depnum_ccdc_archive 'CCDC 2387376'
loop_
_audit_author_name
_audit_author_address
'Alex P. Andrews'
;IISER Thiruvananthapuram
India
;
_audit_update_record             
;
2024-09-27 deposited with the CCDC.	2024-11-08 downloaded from the CCDC.
;
_audit_creation_date             2024-09-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_chemical_formula_moiety         'C13 H12 Br3 N O4'
_chemical_formula_sum            'C13 H12 Br3 N O4'
_chemical_formula_weight         485.955
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
Br -0.38188 2.46625 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95570 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   20.394(4)
_cell_length_b                   12.616(2)
_cell_length_c                   14.923(3)
_cell_angle_alpha                90
_cell_angle_beta                 125.057(5)
_cell_angle_gamma                90
_cell_volume                     3142.9(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1915
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.73
_cell_measurement_theta_min      2.78
_exptl_absorpt_coefficient_mu    7.714
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5339
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1400 before and 0.0547 after correction.
The Ratio of minimum to maximum transmission is 0.7160.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.054
_exptl_crystal_density_meas      2.053
_exptl_crystal_density_method    NONE
_exptl_crystal_description       needle
_exptl_crystal_F_000             1868.240
_exptl_crystal_size_max          0.085
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.028
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_Laue_measured_fraction_full 0.9996
_diffrn_reflns_Laue_measured_fraction_max 0.9997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3091
_diffrn_reflns_point_group_measured_fraction_full 0.9996
_diffrn_reflns_point_group_measured_fraction_max 0.9997
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.13
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.9997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              20
_reflns_limit_h_min              -25
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                1712
_reflns_number_total             3091
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.0373
_refine_diff_density_min         -1.0289
_refine_diff_density_rms         0.2468
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             9.5609
_refine_ls_goodness_of_fit_ref   0.9883
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    17
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3091
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1092
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      0.9883
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0344P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0920
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C2(H2a,H2b,H2c), C13(H13a,H13b,H13c)
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
C1 C 0.6166(4) 0.1183(4) 0.5295(5) 0.079(2) Uani 1.000000 .
H1a H 0.644(2) 0.1742(8) 0.5821(5) 0.119(3) Uiso 1.000000 GR
H1b H 0.5773(5) 0.087(3) 0.5376(11) 0.119(3) Uiso 1.000000 GR
H1c H 0.6545(18) 0.065(2) 0.5413(13) 0.119(3) Uiso 1.000000 GR
C2 C 0.3948(4) 0.0918(4) 0.2764(5) 0.079(2) Uani 1.000000 .
H2a H 0.3539(17) 0.1307(13) 0.2133(6) 0.118(3) Uiso 1.000000 GR
H2b H 0.4374(6) 0.075(3) 0.2691(18) 0.118(3) Uiso 1.000000 GR
H2c H 0.373(2) 0.0274(15) 0.2824(15) 0.118(3) Uiso 1.000000 GR
C3 C 0.5371(3) 0.2533(4) 0.4039(4) 0.0456(14) Uani 1.000000 .
C4 C 0.4579(3) 0.2502(4) 0.3742(4) 0.0438(14) Uani 1.000000 .
C5 C 0.4148(3) 0.3432(4) 0.3505(4) 0.0430(14) Uani 1.000000 .
C6 C 0.4495(3) 0.4426(4) 0.3563(4) 0.0364(12) Uani 1.000000 .
C7 C 0.5297(3) 0.4414(4) 0.3888(4) 0.0337(12) Uani 1.000000 .
C8 C 0.5734(3) 0.3486(4) 0.4115(4) 0.0383(13) Uani 1.000000 .
C9 C 0.4270(3) 0.5510(4) 0.3388(4) 0.0415(13) Uani 1.000000 .
C10 C 0.4912(3) 0.6105(4) 0.3631(4) 0.0393(13) Uani 1.000000 .
C11 C 0.5030(4) 0.7255(5) 0.3647(4) 0.0508(16) Uani 1.000000 .
C12 C 0.5984(4) 0.8588(4) 0.4104(5) 0.074(2) Uani 1.000000 .
H12a H 0.5979(4) 0.8886(4) 0.4699(5) 0.089(2) Uiso 1.000000 R
H12b H 0.5598(4) 0.8972(4) 0.3439(5) 0.089(2) Uiso 1.000000 R
C13 C 0.6781(4) 0.8693(5) 0.4341(5) 0.087(2) Uani 1.000000 .
H13a H 0.7166(5) 0.836(3) 0.5033(17) 0.130(3) Uiso 1.000000 GR
H13b H 0.6792(8) 0.835(3) 0.3776(18) 0.130(3) Uiso 1.000000 GR
H13c H 0.6908(11) 0.9430(5) 0.437(3) 0.130(3) Uiso 1.000000 GR
N1 N 0.5530(2) 0.5426(3) 0.3934(3) 0.0391(10) Uani 1.000000 .
H1 H 0.5999(2) 0.5617(3) 0.4126(3) 0.0470(12) Uiso 1.000000 R
O1 O 0.5782(2) 0.1601(3) 0.4226(3) 0.0579(11) Uani 1.000000 .
O2 O 0.4257(2) 0.1552(3) 0.3734(3) 0.0585(11) Uani 1.000000 .
O4 O 0.5769(2) 0.7478(3) 0.3971(3) 0.0583(10) Uani 1.000000 .
O5 O 0.4512(3) 0.7904(3) 0.3391(3) 0.0708(12) Uani 1.000000 .
Br1 Br 0.67850(3) 0.35630(5) 0.45079(5) 0.0591(2) Uani 1.000000 .
Br2 Br 0.31000(3) 0.33297(5) 0.31371(5) 0.0665(2) Uani 1.000000 .
Br3 Br 0.32582(4) 0.60672(5) 0.28558(5) 0.0663(2) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1a 0.9600 . ?
C1 H1b 0.9600 . ?
C1 H1c 0.9600 . ?
C1 O1 1.414(6) . ?
C2 H2a 0.9600 . ?
C2 H2b 0.9600 . ?
C2 H2c 0.9600 . ?
C2 O2 1.444(6) . ?
C3 C4 1.408(7) . ?
C3 C8 1.382(6) . ?
C3 O1 1.375(5) . ?
C4 C5 1.385(7) . ?
C4 O2 1.363(6) . ?
C5 C6 1.418(6) . ?
C5 Br2 1.880(5) . ?
C6 C7 1.415(6) . ?
C6 C9 1.419(6) . ?
C7 C8 1.391(6) . ?
C7 N1 1.350(5) . ?
C8 Br1 1.872(5) . ?
C9 C10 1.365(6) . ?
C9 Br3 1.871(5) . ?
C10 C11 1.468(7) . ?
C10 N1 1.369(5) . ?
C11 O4 1.323(6) . ?
C11 O5 1.211(6) . ?
C12 H12a 0.9700 . ?
C12 H12b 0.9700 . ?
C12 C13 1.456(7) . ?
C12 O4 1.446(6) . ?
C13 H13a 0.9600 . ?
C13 H13b 0.9600 . ?
C13 H13c 0.9600 . ?
N1 H1 0.8600 . ?

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
H1b C1 H1a 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?
O1 C1 H1a 109.5 . . ?
O1 C1 H1b 109.5 . . ?
O1 C1 H1c 109.5 . . ?
H2b C2 H2a 109.5 . . ?
H2c C2 H2a 109.5 . . ?
H2c C2 H2b 109.5 . . ?
O2 C2 H2a 109.5 . . ?
O2 C2 H2b 109.5 . . ?
O2 C2 H2c 109.5 . . ?
C8 C3 C4 120.9(5) . . ?
O1 C3 C4 119.7(5) . . ?
O1 C3 C8 119.4(5) . . ?
C5 C4 C3 120.2(5) . . ?
O2 C4 C3 119.2(5) . . ?
O2 C4 C5 120.6(5) . . ?
C6 C5 C4 120.8(5) . . ?
Br2 C5 C4 117.7(4) . . ?
Br2 C5 C6 121.5(4) . . ?
C7 C6 C5 116.8(4) . . ?
C9 C6 C5 138.1(5) . . ?
C9 C6 C7 105.1(4) . . ?
C8 C7 C6 123.0(4) . . ?
N1 C7 C6 108.2(4) . . ?
N1 C7 C8 128.8(5) . . ?
C7 C8 C3 118.4(5) . . ?
Br1 C8 C3 122.3(4) . . ?
Br1 C8 C7 119.4(4) . . ?
C10 C9 C6 108.8(4) . . ?
Br3 C9 C6 127.0(4) . . ?
Br3 C9 C10 124.2(4) . . ?
C11 C10 C9 132.1(5) . . ?
N1 C10 C9 107.7(5) . . ?
N1 C10 C11 120.1(5) . . ?
O4 C11 C10 111.0(5) . . ?
O5 C11 C10 123.9(6) . . ?
O5 C11 O4 125.1(6) . . ?
H12b C12 H12a 108.3 . . ?
C13 C12 H12a 109.8(4) . . ?
C13 C12 H12b 109.8(4) . . ?
O4 C12 H12a 109.8(3) . . ?
O4 C12 H12b 109.8(3) . . ?
O4 C12 C13 109.2(5) . . ?
H13a C13 C12 109.5 . . ?
H13b C13 C12 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C12 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
C10 N1 C7 110.1(4) . . ?
H1 N1 C7 124.9(3) . . ?
H1 N1 C10 124.9(3) . . ?
C3 O1 C1 115.2(4) . . ?
C4 O2 C2 115.2(4) . . ?
C12 O4 C11 116.6(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 C3 C4 -84.5(5) . . . . ?
C1 O1 C3 C8 97.2(5) . . . . ?
C2 O2 C4 C3 -81.6(5) . . . . ?
C2 O2 C4 C5 101.1(5) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C3 C4 C5 Br2 -179.0(4) . . . . ?
C3 C8 C7 C6 -1.2(6) . . . . ?
C3 C8 C7 N1 178.2(4) . . . . ?
C4 C5 C6 C7 -1.0(5) . . . . ?
C4 C5 C6 C9 179.5(4) . . . . ?
C5 C6 C7 C8 1.8(5) . . . . ?
C5 C6 C7 N1 -177.7(4) . . . . ?
C5 C6 C9 C10 177.7(7) . . . . ?
C5 C6 C9 Br3 -4.7(7) . . . . ?
C6 C7 C8 Br1 178.6(4) . . . . ?
C6 C7 N1 C10 -1.3(4) . . . . ?
C6 C9 C10 C11 -176.7(4) . . . . ?
C6 C9 C10 N1 1.2(4) . . . . ?
C7 N1 C10 C9 0.1(4) . . . . ?
C7 N1 C10 C11 178.3(4) . . . . ?
C9 C10 C11 O4 178.0(6) . . . . ?
C9 C10 C11 O5 -2.3(6) . . . . ?
C10 C11 O4 C12 -175.4(4) . . . . ?
C11 O4 C12 C13 -173.7(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
