# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_RS_13_0m-combined
_database_code_depnum_ccdc_archive 'CCDC 1843782'
_audit_update_record             
;
2018-05-17 deposited with the CCDC.
2018-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H12 N2, C2 H2 Br3 N O'
_chemical_formula_sum            'C8 H14 Br3 N3 O'
_chemical_formula_weight         407.95

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'
Br Br -0.2901 2.4595 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.4062(4)
_cell_length_b                   20.4294(14)
_cell_length_c                   9.5955(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.369(2)
_cell_angle_gamma                90
_cell_volume                     1254.74(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7036
_cell_measurement_theta_min      2.9124
_cell_measurement_theta_max      37.7185

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.160
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    9.625
_shelx_estimated_absorpt_T_min   0.101
_shelx_estimated_absorpt_T_max   0.645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4550
_exptl_absorpt_correction_T_max  0.7475
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube X-ray source'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12541
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.914
_diffrn_reflns_theta_max         29.573
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             3269
_reflns_number_gt                2726
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Apex3 v2016.9-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2016/6 (Sheldrick, 2015, 2016), 
SHELXLE Rev714 (Hübschle et al., 2011)
;
_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)+(0.0883P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0062(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3269
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1380
_refine_ls_wR_factor_gt          0.1293
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
C1 C -0.0150(9) 0.1741(3) 0.7209(6) 0.0245(13) Uani 1 1 d . . . . .
H1A H 0.125606 0.169888 0.682636 0.029 Uiso 1 1 calc R U . . .
H1B H -0.011684 0.211539 0.786504 0.029 Uiso 1 1 calc R U . . .
C2 C -0.1763(8) 0.1881(3) 0.6003(5) 0.0160(10) Uani 1 1 d . . . . .
H2A H -0.238006 0.232066 0.612383 0.019 Uiso 1 1 calc R U . . .
H2B H -0.106448 0.187366 0.510240 0.019 Uiso 1 1 calc R U . . .
C3 C -0.2714(8) 0.1216(3) 0.8541(5) 0.0204(12) Uani 1 1 d . . . . .
H3C H -0.267660 0.156832 0.924900 0.024 Uiso 1 1 calc R U . . .
H3D H -0.309947 0.080266 0.900529 0.024 Uiso 1 1 calc R U . . .
C4 C -0.4382(8) 0.1382(3) 0.7364(5) 0.0195(12) Uani 1 1 d . . . . .
H4A H -0.551971 0.105374 0.736395 0.023 Uiso 1 1 calc R U . . .
H4B H -0.499360 0.181719 0.754128 0.023 Uiso 1 1 calc R U . . .
C5 C -0.0723(9) 0.0605(3) 0.6940(5) 0.0218(12) Uani 1 1 d . . . . .
H5A H -0.101241 0.018925 0.742440 0.026 Uiso 1 1 calc R U . . .
H5B H 0.064824 0.056421 0.650840 0.026 Uiso 1 1 calc R U . . .
C6 C -0.2447(9) 0.0730(3) 0.5789(5) 0.0201(12) Uani 1 1 d . . . . .
H6A H -0.183037 0.071387 0.486040 0.024 Uiso 1 1 calc R U . . .
H6B H -0.352715 0.038494 0.582416 0.024 Uiso 1 1 calc R U . . .
C7 C 0.2641(7) 0.1338(3) 1.1761(5) 0.0100(9) Uani 1 1 d . . . . .
C8 C 0.3508(7) 0.0723(3) 1.1030(4) 0.0104(9) Uani 1 1 d . . . . .
N1 N -0.0642(6) 0.1146(2) 0.7959(4) 0.0124(8) Uani 1 1 d . . . . .
N2 N -0.3419(6) 0.1382(2) 0.5997(4) 0.0137(9) Uani 1 1 d . . . . .
N3 N 0.2554(6) 0.0555(2) 0.9824(4) 0.0099(8) Uani 1 1 d . . . . .
H3A H 0.301906 0.022080 0.934740 0.012 Uiso 1 1 calc R U . . .
H3B H 0.145945 0.077671 0.950452 0.012 Uiso 1 1 calc R U . . .
Br1 Br 0.31065(7) 0.20879(3) 1.05682(4) 0.01319(16) Uani 1 1 d . . . . .
Br2 Br -0.03463(7) 0.12335(3) 1.20208(4) 0.01338(17) Uani 1 1 d . . . . .
Br3 Br 0.40877(7) 0.14501(3) 1.35708(4) 0.01363(17) Uani 1 1 d . . . . .
O1 O 0.5047(5) 0.04410(19) 1.1555(3) 0.0150(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.455(7) . ?
C1 C2 1.545(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N2 1.471(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N1 1.468(7) . ?
C3 C4 1.559(6) . ?
C3 H3C 0.9900 . ?
C3 H3D 0.9900 . ?
C4 N2 1.472(7) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.475(7) . ?
C5 C6 1.551(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N2 1.487(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.553(7) . ?
C7 Br1 1.943(5) . ?
C7 Br3 1.948(4) . ?
C7 Br2 1.952(5) . ?
C8 O1 1.232(6) . ?
C8 N3 1.331(5) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?

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
N1 C1 C2 111.9(4) . . ?
N1 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
N2 C2 C1 109.6(4) . . ?
N2 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
N2 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
N1 C3 C4 110.4(4) . . ?
N1 C3 H3C 109.6 . . ?
C4 C3 H3C 109.6 . . ?
N1 C3 H3D 109.6 . . ?
C4 C3 H3D 109.6 . . ?
H3C C3 H3D 108.1 . . ?
N2 C4 C3 110.2(4) . . ?
N2 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
N2 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
N1 C5 C6 110.7(4) . . ?
N1 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
N2 C6 C5 110.0(4) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 Br1 107.8(3) . . ?
C8 C7 Br3 109.4(3) . . ?
Br1 C7 Br3 110.7(2) . . ?
C8 C7 Br2 109.9(3) . . ?
Br1 C7 Br2 109.7(2) . . ?
Br3 C7 Br2 109.4(2) . . ?
O1 C8 N3 124.4(5) . . ?
O1 C8 C7 119.3(4) . . ?
N3 C8 C7 116.3(4) . . ?
C1 N1 C3 109.0(4) . . ?
C1 N1 C5 107.5(5) . . ?
C3 N1 C5 108.5(4) . . ?
C2 N2 C4 109.0(4) . . ?
C2 N2 C6 108.4(4) . . ?
C4 N2 C6 108.2(4) . . ?
C8 N3 H3A 120.0 . . ?
C8 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?

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
N1 C1 C2 N2 2.7(7) . . . . ?
N1 C3 C4 N2 3.4(7) . . . . ?
N1 C5 C6 N2 3.8(7) . . . . ?
Br1 C7 C8 O1 112.8(4) . . . . ?
Br3 C7 C8 O1 -7.7(6) . . . . ?
Br2 C7 C8 O1 -127.8(4) . . . . ?
Br1 C7 C8 N3 -64.6(5) . . . . ?
Br3 C7 C8 N3 175.0(3) . . . . ?
Br2 C7 C8 N3 54.9(5) . . . . ?
C2 C1 N1 C3 -59.8(6) . . . . ?
C2 C1 N1 C5 57.7(6) . . . . ?
C4 C3 N1 C1 55.8(6) . . . . ?
C4 C3 N1 C5 -60.9(6) . . . . ?
C6 C5 N1 C1 -60.9(6) . . . . ?
C6 C5 N1 C3 56.8(6) . . . . ?
C1 C2 N2 C4 57.1(6) . . . . ?
C1 C2 N2 C6 -60.4(5) . . . . ?
C3 C4 N2 C2 -60.5(6) . . . . ?
C3 C4 N2 C6 57.1(6) . . . . ?
C5 C6 N2 C2 56.8(5) . . . . ?
C5 C6 N2 C4 -61.3(6) . . . . ?

_refine_diff_density_max         2.297
_refine_diff_density_min         -1.416
_refine_diff_density_rms         0.298



####################################################################### 
# 
# 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_RS32_0m
_database_code_depnum_ccdc_archive 'CCDC 1843787'
_audit_update_record             
;
2018-05-17 deposited with the CCDC.
2018-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H24 Br N4, C7 H4 N O3 S'
_chemical_formula_sum            'C19 H28 Br N5 O3 S'
_chemical_formula_weight         486.42

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_H-M_alt        'P 32 2 1'
_space_group_name_Hall           'P 32 2"'

_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'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'y, x, -z'
'-x, -x+y, -z+2/3'
'x-y, -y, -z+1/3'

_cell_length_a                   9.8558(5)
_cell_length_b                   9.8558(5)
_cell_length_c                   18.9035(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1590.22(19)
_cell_formula_units_Z            3
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9962
_cell_measurement_theta_min      3.2184
_cell_measurement_theta_max      36.2568

_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             756
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.330
_exptl_absorpt_coefficient_mu    2.068
_shelx_estimated_absorpt_T_min   0.437
_shelx_estimated_absorpt_T_max   0.549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6026
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube X-ray source'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39226
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.216
_diffrn_reflns_theta_max         36.367
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5144
_reflns_number_gt                4167
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

_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       'Apex3 v2016.9-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2017/1 (Sheldrick, 2017), 
SHELXLE Rev859 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The oxo-benzoisothiazolide-dioxide fragment is 1:1 disordered around a 
two fold axis. The benzene ring was restrained to resemble an ideal hexagon 
with C-H distances of 1.39 Angstrom. 

The ethylene moieties of the diazabicyclooctane unit were refined as 
disordered. The two disordered moieties were restrained to have similar 
geometries. Uij components of ADPs for disordered atoms closer to each other 
than 1.7 Angstrom were restrained to be similar. Subject to these conditions 
the occupancy ratio refined to 0.601(8) to 0.3999(8).

Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0306P)²+0.1893P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0127(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.012(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5144
_refine_ls_number_parameters     234
_refine_ls_number_restraints     264
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0661
_refine_ls_wR_factor_gt          0.0623
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.033
_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
N1 N 0.77338(13) 0.54626(15) 0.28610(7) 0.0181(2) Uani 0.601(8) 1 d . U P A 1
N2 N 0.503(6) 0.412(6) 0.229(3) 0.0231(3) Uani 0.601(8) 1 d . U P A 1
C1 C 0.6687(4) 0.3983(4) 0.3251(2) 0.0245(8) Uani 0.601(8) 1 d . U P A 1
H1A H 0.650679 0.422385 0.373905 0.029 Uiso 0.601(8) 1 calc R U P A 1
H1B H 0.717271 0.331569 0.327708 0.029 Uiso 0.601(8) 1 calc R U P A 1
C2 C 0.5121(8) 0.3128(8) 0.2844(3) 0.0256(10) Uani 0.601(8) 1 d . U P A 1
H2A H 0.501109 0.216378 0.262706 0.031 Uiso 0.601(8) 1 calc R U P A 1
H2B H 0.424242 0.281589 0.317949 0.031 Uiso 0.601(8) 1 calc R U P A 1
C3 C 0.7078(5) 0.6523(5) 0.2909(3) 0.0269(8) Uani 0.601(8) 1 d . U P A 1
H3A H 0.770243 0.746987 0.261725 0.032 Uiso 0.601(8) 1 calc R U P A 1
H3B H 0.710006 0.685416 0.340578 0.032 Uiso 0.601(8) 1 calc R U P A 1
C4 C 0.5379(11) 0.5613(10) 0.2638(5) 0.0285(13) Uani 0.601(8) 1 d . U P A 1
H4A H 0.465095 0.538064 0.304029 0.034 Uiso 0.601(8) 1 calc R U P A 1
H4B H 0.520357 0.627273 0.229713 0.034 Uiso 0.601(8) 1 calc R U P A 1
C5 C 0.7862(4) 0.5093(5) 0.21190(18) 0.0270(8) Uani 0.601(8) 1 d . U P A 1
H5A H 0.819566 0.429911 0.209299 0.032 Uiso 0.601(8) 1 calc R U P A 1
H5B H 0.864306 0.604640 0.186663 0.032 Uiso 0.601(8) 1 calc R U P A 1
C6 C 0.6211(12) 0.4445(9) 0.1779(5) 0.0315(14) Uani 0.601(8) 1 d . U P A 1
H6A H 0.624637 0.522061 0.143524 0.038 Uiso 0.601(8) 1 calc R U P A 1
H6B H 0.593619 0.347159 0.151598 0.038 Uiso 0.601(8) 1 calc R U P A 1
N1B N 0.77338(13) 0.54626(15) 0.28610(7) 0.0181(2) Uani 0.399(8) 1 d . U P A 2
N2B N 0.503(8) 0.412(9) 0.229(5) 0.0231(3) Uani 0.399(8) 1 d . U P A 2
C1B C 0.6941(7) 0.3742(6) 0.2979(4) 0.0285(12) Uani 0.399(8) 1 d . U P A 2
H1C H 0.690414 0.352253 0.349212 0.034 Uiso 0.399(8) 1 calc R U P A 2
H1D H 0.753914 0.330899 0.274309 0.034 Uiso 0.399(8) 1 calc R U P A 2
C2B C 0.5258(13) 0.2954(13) 0.2678(6) 0.0265(15) Uani 0.399(8) 1 d . U P A 2
H2C H 0.508531 0.208892 0.235639 0.032 Uiso 0.399(8) 1 calc R U P A 2
H2D H 0.448998 0.250849 0.306918 0.032 Uiso 0.399(8) 1 calc R U P A 2
C3B C 0.6781(7) 0.6085(8) 0.3160(4) 0.0266(12) Uani 0.399(8) 1 d . U P A 2
H3C H 0.733495 0.723833 0.310600 0.032 Uiso 0.399(8) 1 calc R U P A 2
H3D H 0.660774 0.583584 0.367104 0.032 Uiso 0.399(8) 1 calc R U P A 2
C4B C 0.5164(16) 0.5334(15) 0.2764(7) 0.0239(16) Uani 0.399(8) 1 d . U P A 2
H4C H 0.429900 0.487830 0.311300 0.029 Uiso 0.399(8) 1 calc R U P A 2
H4D H 0.508445 0.615011 0.249320 0.029 Uiso 0.399(8) 1 calc R U P A 2
C5B C 0.7906(6) 0.5787(9) 0.2078(3) 0.0312(13) Uani 0.399(8) 1 d . U P A 2
H5C H 0.866147 0.550767 0.187595 0.037 Uiso 0.399(8) 1 calc R U P A 2
H5D H 0.830851 0.691548 0.199105 0.037 Uiso 0.399(8) 1 calc R U P A 2
C6B C 0.6285(16) 0.4801(14) 0.1721(8) 0.0269(18) Uani 0.399(8) 1 d . U P A 2
H6C H 0.608181 0.546886 0.139704 0.032 Uiso 0.399(8) 1 calc R U P A 2
H6D H 0.626819 0.394383 0.144072 0.032 Uiso 0.399(8) 1 calc R U P A 2
Br1 Br 1.000000 0.65905(2) 0.333333 0.01891(6) Uani 1 2 d S T P . .
S1 S 0.3416(5) 0.3534(5) 0.5019(4) 0.0263(8) Uani 0.5 1 d . . P B -1
O1 O 0.0782(5) 0.3178(4) 0.35715(19) 0.0611(11) Uani 0.5 1 d . . P B -1
O2 O 0.4760(4) 0.3247(5) 0.4809(2) 0.0508(9) Uani 0.5 1 d . . P B -1
O3 O 0.3694(6) 0.4469(4) 0.55720(18) 0.0596(11) Uani 0.5 1 d . . P B -1
N3 N 0.2942(4) 0.4080(4) 0.42915(17) 0.0346(7) Uani 0.5 1 d . . P B -1
C7 C 0.1488(5) 0.3007(5) 0.4074(2) 0.0348(8) Uani 0.5 1 d . . P B -1
C8 C 0.1736(9) 0.1703(8) 0.5081(5) 0.0258(15) Uani 0.5 1 d G . P B -1
C9 C 0.0771(8) 0.1573(7) 0.4518(4) 0.0326(17) Uani 0.5 1 d G . P B -1
C10 C -0.0641(6) 0.0192(8) 0.4417(3) 0.0461(17) Uani 0.5 1 d G . P B -1
H10 H -0.130077 0.010285 0.403177 0.055 Uiso 0.5 1 calc R U P B -1
C11 C -0.1088(8) -0.1059(8) 0.4878(4) 0.060(2) Uani 0.5 1 d G . P B -1
H11 H -0.205302 -0.200289 0.480877 0.072 Uiso 0.5 1 calc R U P B -1
C12 C -0.0123(9) -0.0929(6) 0.5441(3) 0.062(3) Uani 0.5 1 d G . P B -1
H12 H -0.042819 -0.178358 0.575663 0.075 Uiso 0.5 1 calc R U P B -1
C13 C 0.1289(8) 0.0452(8) 0.5543(4) 0.0356(15) Uani 0.5 1 d G . P B -1
H13 H 0.194890 0.054148 0.592750 0.043 Uiso 0.5 1 calc R U P B -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.470(3) . ?
N1 C3 1.481(4) . ?
N1 C1 1.493(4) . ?
N1 Br1 2.1304(12) . ?
N2 C6 1.42(6) . ?
N2 C2 1.47(6) . ?
N2 C4 1.49(6) . ?
C1 C2 1.544(8) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.540(10) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.559(11) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
N1B C3B 1.468(6) . ?
N1B C1B 1.487(5) . ?
N1B C5B 1.506(5) . ?
N1B Br1 2.1304(12) . ?
N2B C4B 1.45(10) . ?
N2B C2B 1.47(10) . ?
N2B C6B 1.52(8) . ?
C1B C2B 1.546(13) . ?
C1B H1C 0.9900 . ?
C1B H1D 0.9900 . ?
C2B H2C 0.9900 . ?
C2B H2D 0.9900 . ?
C3B C4B 1.570(16) . ?
C3B H3C 0.9900 . ?
C3B H3D 0.9900 . ?
C4B H4C 0.9900 . ?
C4B H4D 0.9900 . ?
C5B C6B 1.549(16) . ?
C5B H5C 0.9900 . ?
C5B H5D 0.9900 . ?
C6B H6C 0.9900 . ?
C6B H6D 0.9900 . ?
S1 O3 1.328(8) . ?
S1 O2 1.539(9) . ?
S1 N3 1.629(9) . ?
S1 C8 1.739(3) . ?
O1 C7 1.238(5) . ?
N3 C7 1.352(6) . ?
C7 C9 1.484(7) . ?
C8 C9 1.3900 . ?
C8 C13 1.3900 . ?
C9 C10 1.3900 . ?
C10 C11 1.3900 . ?
C10 H10 0.9500 . ?
C11 C12 1.3900 . ?
C11 H11 0.9500 . ?
C12 C13 1.3900 . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

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
C5 N1 C3 110.8(2) . . ?
C5 N1 C1 109.4(2) . . ?
C3 N1 C1 109.0(2) . . ?
C5 N1 Br1 109.37(15) . . ?
C3 N1 Br1 108.62(17) . . ?
C1 N1 Br1 109.57(15) . . ?
C6 N2 C2 109(5) . . ?
C6 N2 C4 109(3) . . ?
C2 N2 C4 106(4) . . ?
N1 C1 C2 107.5(3) . . ?
N1 C1 H1A 110.2 . . ?
C2 C1 H1A 110.2 . . ?
N1 C1 H1B 110.2 . . ?
C2 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
N2 C2 C1 111.6(17) . . ?
N2 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
N2 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
N1 C3 C4 107.4(5) . . ?
N1 C3 H3A 110.2 . . ?
C4 C3 H3A 110.2 . . ?
N1 C3 H3B 110.2 . . ?
C4 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
N2 C4 C3 112(2) . . ?
N2 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
N2 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
N1 C5 C6 107.1(5) . . ?
N1 C5 H5A 110.3 . . ?
C6 C5 H5A 110.3 . . ?
N1 C5 H5B 110.3 . . ?
C6 C5 H5B 110.3 . . ?
H5A C5 H5B 108.5 . . ?
N2 C6 C5 112(2) . . ?
N2 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
N2 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
C3B N1B C1B 109.7(3) . . ?
C3B N1B C5B 108.5(4) . . ?
C1B N1B C5B 109.2(3) . . ?
C3B N1B Br1 110.1(2) . . ?
C1B N1B Br1 110.4(2) . . ?
C5B N1B Br1 108.9(2) . . ?
C4B N2B C2B 110(6) . . ?
C4B N2B C6B 111(4) . . ?
C2B N2B C6B 107(6) . . ?
N1B C1B C2B 109.7(5) . . ?
N1B C1B H1C 109.7 . . ?
C2B C1B H1C 109.7 . . ?
N1B C1B H1D 109.7 . . ?
C2B C1B H1D 109.7 . . ?
H1C C1B H1D 108.2 . . ?
N2B C2B C1B 110(3) . . ?
N2B C2B H2C 109.8 . . ?
C1B C2B H2C 109.8 . . ?
N2B C2B H2D 109.8 . . ?
C1B C2B H2D 109.8 . . ?
H2C C2B H2D 108.2 . . ?
N1B C3B C4B 109.3(7) . . ?
N1B C3B H3C 109.8 . . ?
C4B C3B H3C 109.8 . . ?
N1B C3B H3D 109.8 . . ?
C4B C3B H3D 109.8 . . ?
H3C C3B H3D 108.3 . . ?
N2B C4B C3B 110(4) . . ?
N2B C4B H4C 109.7 . . ?
C3B C4B H4C 109.7 . . ?
N2B C4B H4D 109.7 . . ?
C3B C4B H4D 109.7 . . ?
H4C C4B H4D 108.2 . . ?
N1B C5B C6B 108.9(5) . . ?
N1B C5B H5C 109.9 . . ?
C6B C5B H5C 109.9 . . ?
N1B C5B H5D 109.9 . . ?
C6B C5B H5D 109.9 . . ?
H5C C5B H5D 108.3 . . ?
N2B C6B C5B 109(3) . . ?
N2B C6B H6C 109.9 . . ?
C5B C6B H6C 109.9 . . ?
N2B C6B H6D 109.9 . . ?
C5B C6B H6D 109.9 . . ?
H6C C6B H6D 108.3 . . ?
N1B Br1 N1 179.73(7) . 5_765 ?
N1 Br1 N1 179.73(7) . 5_765 ?
O3 S1 O2 115.7(5) . . ?
O3 S1 N3 115.4(6) . . ?
O2 S1 N3 105.0(5) . . ?
O3 S1 C8 115.2(6) . . ?
O2 S1 C8 106.7(6) . . ?
N3 S1 C8 96.8(4) . . ?
C7 N3 S1 111.4(3) . . ?
O1 C7 N3 125.1(4) . . ?
O1 C7 C9 122.1(5) . . ?
N3 C7 C9 112.8(4) . . ?
C9 C8 C13 120.0 . . ?
C9 C8 S1 107.3(5) . . ?
C13 C8 S1 132.6(5) . . ?
C8 C9 C10 120.0 . . ?
C8 C9 C7 111.5(5) . . ?
C10 C9 C7 128.4(5) . . ?
C11 C10 C9 120.0 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C8 120.0 . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?

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
C5 N1 C1 C2 -54.3(3) . . . . ?
C3 N1 C1 C2 67.0(3) . . . . ?
Br1 N1 C1 C2 -174.2(2) . . . . ?
C6 N2 C2 C1 64(3) . . . . ?
C4 N2 C2 C1 -53(4) . . . . ?
N1 C1 C2 N2 -10(3) . . . . ?
C5 N1 C3 C4 65.8(4) . . . . ?
C1 N1 C3 C4 -54.7(4) . . . . ?
Br1 N1 C3 C4 -174.0(4) . . . . ?
C6 N2 C4 C3 -51(4) . . . . ?
C2 N2 C4 C3 66(3) . . . . ?
N1 C3 C4 N2 -11(2) . . . . ?
C3 N1 C5 C6 -54.1(4) . . . . ?
C1 N1 C5 C6 66.2(4) . . . . ?
Br1 N1 C5 C6 -173.8(3) . . . . ?
C2 N2 C6 C5 -52(3) . . . . ?
C4 N2 C6 C5 64(4) . . . . ?
N1 C5 C6 N2 -11(3) . . . . ?
C3B N1B C1B C2B 54.7(6) . . . . ?
C5B N1B C1B C2B -64.2(6) . . . . ?
Br1 N1B C1B C2B 176.2(4) . . . . ?
C4B N2B C2B C1B -64(5) . . . . ?
C6B N2B C2B C1B 57(5) . . . . ?
N1B C1B C2B N2B 7(4) . . . . ?
C1B N1B C3B C4B -62.7(6) . . . . ?
C5B N1B C3B C4B 56.6(6) . . . . ?
Br1 N1B C3B C4B 175.7(5) . . . . ?
C2B N2B C4B C3B 56(5) . . . . ?
C6B N2B C4B C3B -63(6) . . . . ?
N1B C3B C4B N2B 7(4) . . . . ?
C3B N1B C5B C6B -67.2(7) . . . . ?
C1B N1B C5B C6B 52.4(7) . . . . ?
Br1 N1B C5B C6B 173.0(6) . . . . ?
C4B N2B C6B C5B 52(7) . . . . ?
C2B N2B C6B C5B -68(5) . . . . ?
N1B C5B C6B N2B 12(4) . . . . ?
O3 S1 N3 C7 -118.1(4) . . . . ?
O2 S1 N3 C7 113.3(3) . . . . ?
C8 S1 N3 C7 4.0(7) . . . . ?
S1 N3 C7 O1 173.6(5) . . . . ?
S1 N3 C7 C9 -4.7(7) . . . . ?
O3 S1 C8 C9 120.1(6) . . . . ?
O2 S1 C8 C9 -109.9(5) . . . . ?
N3 S1 C8 C9 -2.1(6) . . . . ?
O3 S1 C8 C13 -62.9(11) . . . . ?
O2 S1 C8 C13 67.0(10) . . . . ?
N3 S1 C8 C13 174.9(7) . . . . ?
C13 C8 C9 C10 0.0 . . . . ?
S1 C8 C9 C10 177.4(10) . . . . ?
C13 C8 C9 C7 -177.7(7) . . . . ?
S1 C8 C9 C7 -0.3(5) . . . . ?
O1 C7 C9 C8 -175.2(5) . . . . ?
N3 C7 C9 C8 3.2(4) . . . . ?
O1 C7 C9 C10 7.4(11) . . . . ?
N3 C7 C9 C10 -174.3(7) . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C7 C9 C10 C11 177.2(8) . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 C8 0.0 . . . . ?
C9 C8 C13 C12 0.0 . . . . ?
S1 C8 C13 C12 -176.6(12) . . . . ?

_refine_diff_density_max         0.404
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.068



####################################################################### 
# 
# 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_cx0500
_database_code_depnum_ccdc_archive 'CCDC 1843788'
_audit_update_record             
;
2018-05-17 deposited with the CCDC.
2018-06-27 downloaded from the CCDC.
;
_audit_creation_date             2015-07-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C6 H12 N2, Br3 C N O2, C H Cl3'
_chemical_formula_sum            'C8 H13 Br3 Cl3 N3 O2'
_chemical_formula_weight         529.29
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   14.314(2)
_cell_length_b                   18.260(3)
_cell_length_c                   6.4262(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1679.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9864
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.066
_cell_measurement_theta_min      3.924
_shelx_estimated_absorpt_T_max   0.138
_shelx_estimated_absorpt_T_min   0.068
_exptl_absorpt_coefficient_mu    13.331
_exptl_absorpt_correction_T_max  0.1621
_exptl_absorpt_correction_T_min  0.0447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1320 before and 0.0665 after correction.
The Ratio of minimum to maximum transmission is 0.2758.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.093
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.436
_exptl_crystal_size_mid          0.385
_exptl_crystal_size_min          0.246
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.944
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9754
_diffrn_reflns_point_group_measured_fraction_full 0.855
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.061
_diffrn_reflns_theta_min         4.844
_diffrn_ambient_temperature      99.96
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Quazar optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   microsource
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.652
_reflns_Friedel_fraction_full    0.746
_reflns_Friedel_fraction_max     0.789
_reflns_number_gt                2596
_reflns_number_total             2603
_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       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.118
_refine_ls_abs_structure_details 
;
 Flack x determined using 1023 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.09(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2603
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0304
_refine_ls_restrained_S_all      1.107
_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)+(0.0403P)²+1.4290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0768
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
N1 N 0.4604(3) 0.2116(3) 0.4371(9) 0.0272(12) Uani 1 1 d . . . . .
N3 N 0.3596(3) 0.2865(3) 0.1885(9) 0.0260(11) Uani 1 1 d . . . . .
C3 C 0.3608(4) 0.2034(4) 0.4883(12) 0.0334(14) Uani 1 1 d . . . . .
H3A H 0.3499 0.2189 0.6338 0.040 Uiso 1 1 calc R . . . .
H3B H 0.3427 0.1512 0.4759 0.040 Uiso 1 1 calc R . . . .
C4 C 0.4747(5) 0.1865(4) 0.2234(11) 0.0326(15) Uani 1 1 d . . . . .
H4A H 0.4589 0.1338 0.2132 0.039 Uiso 1 1 calc R . . . .
H4B H 0.5411 0.1926 0.1845 0.039 Uiso 1 1 calc R . . . .
C5 C 0.4854(5) 0.2890(3) 0.4528(13) 0.0342(15) Uani 1 1 d . . . . .
H5A H 0.5526 0.2954 0.4213 0.041 Uiso 1 1 calc R . . . .
H5B H 0.4741 0.3065 0.5964 0.041 Uiso 1 1 calc R . . . .
C6 C 0.3007(5) 0.2496(4) 0.3421(12) 0.0318(14) Uani 1 1 d . . . . .
H6A H 0.2549 0.2178 0.2701 0.038 Uiso 1 1 calc R . . . .
H6B H 0.2656 0.2865 0.4236 0.038 Uiso 1 1 calc R . . . .
C7 C 0.4127(5) 0.2306(4) 0.0727(11) 0.0341(16) Uani 1 1 d . . . . .
H7A H 0.4523 0.2547 -0.0336 0.041 Uiso 1 1 calc R . . . .
H7B H 0.3690 0.1972 0.0005 0.041 Uiso 1 1 calc R . . . .
C8 C 0.4265(4) 0.3344(4) 0.2986(12) 0.0338(16) Uani 1 1 d . . . . .
H8A H 0.3921 0.3730 0.3749 0.041 Uiso 1 1 calc R . . . .
H8B H 0.4682 0.3586 0.1964 0.041 Uiso 1 1 calc R . . . .
Br1 Br 0.91168(4) 0.51072(3) 0.51063(12) 0.02899(19) Uani 1 1 d . . . . .
Br2 Br 0.93138(4) 0.63415(3) 0.16094(10) 0.02430(19) Uani 1 1 d . . . . .
Br3 Br 0.75312(4) 0.63231(3) 0.46937(12) 0.02526(19) Uani 1 1 d . . . . .
O2 O 0.7317(4) 0.5544(3) 0.0642(10) 0.0490(15) Uani 1 1 d . . . . .
O3 O 0.8218(4) 0.4640(3) 0.1264(9) 0.0441(13) Uani 1 1 d . . . . .
N2 N 0.7944(3) 0.5258(3) 0.1575(9) 0.0241(10) Uani 1 1 d . . . . .
C1 C 0.8443(4) 0.5725(3) 0.3216(10) 0.0210(11) Uani 1 1 d . . . . .
Cl1 Cl 0.65527(11) 0.42923(9) 0.4875(3) 0.0382(4) Uani 1 1 d . . . . .
Cl2 Cl 0.66511(12) 0.33452(10) 0.8485(3) 0.0450(5) Uani 1 1 d . . . . .
Cl3 Cl 0.53489(17) 0.45459(12) 0.8369(4) 0.0631(6) Uani 1 1 d . . . . .
C9 C 0.6455(5) 0.4244(4) 0.7606(13) 0.0382(17) Uani 1 1 d . . . . .
H9 H 0.6936 0.4573 0.8239 0.046 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
N1 C3 1.471(8) . ?
N1 C4 1.462(9) . ?
N1 C5 1.461(8) . ?
N3 C6 1.463(9) . ?
N3 C7 1.474(9) . ?
N3 C8 1.478(9) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C6 1.528(10) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C7 1.540(10) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C8 1.543(10) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
Br1 C1 1.918(6) . ?
Br2 C1 1.972(6) . ?
Br3 C1 1.948(6) . ?
O2 N2 1.200(7) . ?
O3 N2 1.210(7) . ?
N2 C1 1.532(8) . ?
Cl1 C9 1.763(8) . ?
Cl2 C9 1.759(8) . ?
Cl3 C9 1.747(8) . ?
C9 H9 1.0000 . ?

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
C4 N1 C3 108.2(5) . . ?
C5 N1 C3 108.7(5) . . ?
C5 N1 C4 109.5(6) . . ?
C6 N3 C7 108.6(5) . . ?
C6 N3 C8 108.9(5) . . ?
C7 N3 C8 108.5(5) . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
N1 C3 C6 110.6(5) . . ?
H3A C3 H3B 108.1 . . ?
C6 C3 H3A 109.5 . . ?
C6 C3 H3B 109.5 . . ?
N1 C4 H4A 109.6 . . ?
N1 C4 H4B 109.6 . . ?
N1 C4 C7 110.3(5) . . ?
H4A C4 H4B 108.1 . . ?
C7 C4 H4A 109.6 . . ?
C7 C4 H4B 109.6 . . ?
N1 C5 H5A 109.7 . . ?
N1 C5 H5B 109.7 . . ?
N1 C5 C8 110.0(5) . . ?
H5A C5 H5B 108.2 . . ?
C8 C5 H5A 109.7 . . ?
C8 C5 H5B 109.7 . . ?
N3 C6 C3 110.2(5) . . ?
N3 C6 H6A 109.6 . . ?
N3 C6 H6B 109.6 . . ?
C3 C6 H6A 109.6 . . ?
C3 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
N3 C7 C4 110.0(5) . . ?
N3 C7 H7A 109.7 . . ?
N3 C7 H7B 109.7 . . ?
C4 C7 H7A 109.7 . . ?
C4 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
N3 C8 C5 110.0(5) . . ?
N3 C8 H8A 109.7 . . ?
N3 C8 H8B 109.7 . . ?
C5 C8 H8A 109.7 . . ?
C5 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
O2 N2 O3 124.4(6) . . ?
O2 N2 C1 116.7(5) . . ?
O3 N2 C1 118.8(5) . . ?
Br1 C1 Br2 110.4(3) . . ?
Br1 C1 Br3 111.0(3) . . ?
Br3 C1 Br2 111.0(3) . . ?
N2 C1 Br1 110.0(4) . . ?
N2 C1 Br2 104.6(4) . . ?
N2 C1 Br3 109.6(4) . . ?
Cl1 C9 H9 108.7 . . ?
Cl2 C9 Cl1 110.7(4) . . ?
Cl2 C9 H9 108.7 . . ?
Cl3 C9 Cl1 109.6(4) . . ?
Cl3 C9 Cl2 110.4(4) . . ?
Cl3 C9 H9 108.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C3 C6 N3 2.1(8) . . . . ?
N1 C4 C7 N3 1.6(8) . . . . ?
N1 C5 C8 N3 2.6(8) . . . . ?
C3 N1 C4 C7 58.0(7) . . . . ?
C3 N1 C5 C8 -60.3(7) . . . . ?
C4 N1 C3 C6 -60.6(7) . . . . ?
C4 N1 C5 C8 57.7(7) . . . . ?
C5 N1 C3 C6 58.2(7) . . . . ?
C5 N1 C4 C7 -60.3(7) . . . . ?
C6 N3 C7 C4 -60.2(7) . . . . ?
C6 N3 C8 C5 57.5(7) . . . . ?
C7 N3 C6 C3 57.9(7) . . . . ?
C7 N3 C8 C5 -60.5(7) . . . . ?
C8 N3 C6 C3 -60.1(7) . . . . ?
C8 N3 C7 C4 58.0(7) . . . . ?
O2 N2 C1 Br1 161.4(5) . . . . ?
O2 N2 C1 Br2 -80.0(6) . . . . ?
O2 N2 C1 Br3 39.1(7) . . . . ?
O3 N2 C1 Br1 -20.5(7) . . . . ?
O3 N2 C1 Br2 98.1(6) . . . . ?
O3 N2 C1 Br3 -142.8(5) . . . . ?

# end Validation Reply Form
_olex2_date_sample_data_collection 2015-07-09
_olex2_date_sample_submission    2015-07-08
_olex2_submission_original_sample_id cx0500
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT431_cx0500              
;
PROBLEM: Short Inter HL..A  Contact Br2    ..  N1      ..       2.54 Ang.  
RESPONSE: We are confident in our model
;
####################################################################### 
# 
# 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_RS55_0m
_database_code_depnum_ccdc_archive 'CCDC 1843785'
_audit_update_record             
;
2018-05-17 deposited with the CCDC.
2018-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H12 Br4 N2, C H2 Cl2'
_chemical_formula_sum            'C7 H14 Br4 Cl2 N2'
_chemical_formula_weight         516.74

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_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'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   7.7632(3)
_cell_length_b                   7.4280(4)
_cell_length_c                   12.8269(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.7339(15)
_cell_angle_gamma                90
_cell_volume                     731.09(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9944
_cell_measurement_theta_min      3.1787
_cell_measurement_theta_max      33.0698

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.347
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    11.349
_shelx_estimated_absorpt_T_min   0.164
_shelx_estimated_absorpt_T_max   0.343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3861
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.
(2015). J. Appl. Cryst. 48 3-10.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube X-ray source'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36166
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.179
_diffrn_reflns_theta_max         33.195
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2979
_reflns_number_gt                2527
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Apex3 v2016.9-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/1 (Sheldrick, 2015, 2018), 
SHELXLE Rev882 (Hübschle et al., 2011)
;
_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)+(0.0263P)²+0.5313P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0095(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2979
_refine_ls_number_parameters     86
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0583
_refine_ls_wR_factor_gt          0.0546
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.002
_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
C1 C 0.3797(3) 0.750000 0.84171(18) 0.0164(4) Uani 1 2 d S T P . .
H1A H 0.454231 0.858056 0.855771 0.020 Uiso 0.5 1 calc R U P . .
H1AB H 0.454231 0.641944 0.855771 0.020 Uiso 0.5 1 calc R U P . .
C2 C 0.2376(3) 0.750000 0.91417(18) 0.0156(4) Uani 1 2 d S T P . .
H2A H 0.249816 0.641914 0.959856 0.019 Uiso 0.5 1 calc R U P . .
H2AB H 0.249816 0.858086 0.959856 0.019 Uiso 0.5 1 calc R U P . .
C3 C 0.1845(2) 0.5863(2) 0.70718(13) 0.0172(3) Uani 1 1 d . . . . .
H3A H 0.257589 0.477050 0.720295 0.021 Uiso 1 1 calc R U . . .
H3AB H 0.129847 0.586327 0.632237 0.021 Uiso 1 1 calc R U . . .
C4 C 0.0418(2) 0.5865(2) 0.77962(13) 0.0164(3) Uani 1 1 d . . . . .
H4A H -0.075224 0.586353 0.736330 0.020 Uiso 1 1 calc R U . . .
H4AB H 0.052636 0.477365 0.824468 0.020 Uiso 1 1 calc R U . . .
C5 C 0.3138(3) 0.750000 0.3691(2) 0.0237(5) Uani 1 2 d S T P . .
H5A H 0.375531 0.857800 0.401192 0.028 Uiso 0.5 1 calc R U P . .
H5AB H 0.375531 0.642200 0.401192 0.028 Uiso 0.5 1 calc R U P . .
N1 N 0.2936(2) 0.750000 0.73043(16) 0.0139(4) Uani 1 2 d S T P . .
N2 N 0.0641(2) 0.750000 0.84655(15) 0.0132(3) Uani 1 2 d S T P . .
Br1 Br 0.50026(3) 0.750000 0.63436(2) 0.01509(6) Uani 1 2 d S T P . .
Br2 Br 0.74352(3) 0.750000 0.52383(2) 0.02205(7) Uani 1 2 d S T P . .
Br3 Br -0.13090(3) 0.750000 0.95061(2) 0.01519(6) Uani 1 2 d S T P . .
Br4 Br -0.35394(3) 0.750000 1.07605(2) 0.01734(6) Uani 1 2 d S T P . .
Cl1 Cl 0.31914(11) 0.750000 0.23181(6) 0.03845(19) Uani 1 2 d S T P . .
Cl2 Cl 0.09708(8) 0.750000 0.39699(5) 0.02289(13) Uani 1 2 d S T P . .


_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
C1 N1 1.481(3) . ?
C1 C2 1.547(3) . ?
C1 H1A 0.9900 . ?
C1 H1AB 0.9900 . ?
C2 N2 1.487(3) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 N1 1.486(2) . ?
C3 C4 1.550(2) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 N2 1.4824(19) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 Cl1 1.768(3) . ?
C5 Cl2 1.772(3) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
N1 Br1 2.166(2) . ?
N2 Br3 2.1647(19) . ?
Br1 Br2 2.5278(3) . ?
Br3 Br4 2.5364(3) . ?

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
N1 C1 C2 108.70(18) . . ?
N1 C1 H1A 109.9 . . ?
C2 C1 H1A 109.9 . . ?
N1 C1 H1AB 109.9 . . ?
C2 C1 H1AB 109.9 . . ?
H1A C1 H1AB 108.3 . . ?
N2 C2 C1 108.36(18) . . ?
N2 C2 H2A 110.0 . . ?
C1 C2 H2A 110.0 . . ?
N2 C2 H2AB 110.0 . . ?
C1 C2 H2AB 110.0 . . ?
H2A C2 H2AB 108.4 . . ?
N1 C3 C4 108.46(14) . . ?
N1 C3 H3A 110.0 . . ?
C4 C3 H3A 110.0 . . ?
N1 C3 H3AB 110.0 . . ?
C4 C3 H3AB 110.0 . . ?
H3A C3 H3AB 108.4 . . ?
N2 C4 C3 108.45(14) . . ?
N2 C4 H4A 110.0 . . ?
C3 C4 H4A 110.0 . . ?
N2 C4 H4AB 110.0 . . ?
C3 C4 H4AB 110.0 . . ?
H4A C4 H4AB 108.4 . . ?
Cl1 C5 Cl2 111.56(15) . . ?
Cl1 C5 H5A 109.3 . . ?
Cl2 C5 H5A 109.3 . . ?
Cl1 C5 H5AB 109.3 . . ?
Cl2 C5 H5AB 109.3 . . ?
H5A C5 H5AB 108.0 . . ?
C1 N1 C3 110.69(12) . . ?
C1 N1 C3 110.69(12) . 4_575 ?
C3 N1 C3 109.81(18) . 4_575 ?
C1 N1 Br1 106.48(13) . . ?
C3 N1 Br1 109.55(10) . . ?
C3 N1 Br1 109.55(10) 4_575 . ?
C4 N2 C4 110.05(18) . 4_575 ?
C4 N2 C2 110.71(11) . . ?
C4 N2 C2 110.71(11) 4_575 . ?
C4 N2 Br3 109.03(10) . . ?
C4 N2 Br3 109.03(10) 4_575 . ?
C2 N2 Br3 107.25(14) . . ?
N1 Br1 Br2 179.45(5) . . ?
N2 Br3 Br4 178.72(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 0.000(1) . . . . ?
N1 C3 C4 N2 0.09(18) . . . . ?
C2 C1 N1 C3 -61.00(12) . . . . ?
C2 C1 N1 C3 61.00(12) . . . 4_575 ?
C2 C1 N1 Br1 180.000(1) . . . . ?
C4 C3 N1 C1 60.96(18) . . . . ?
C4 C3 N1 C3 -61.6(2) . . . 4_575 ?
C4 C3 N1 Br1 178.09(10) . . . . ?
C3 C4 N2 C4 61.6(2) . . . 4_575 ?
C3 C4 N2 C2 -61.11(18) . . . . ?
C3 C4 N2 Br3 -178.86(11) . . . . ?
C1 C2 N2 C4 61.17(12) . . . . ?
C1 C2 N2 C4 -61.16(12) . . . 4_575 ?
C1 C2 N2 Br3 180.000(1) . . . . ?

_refine_diff_density_max         1.142
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.149



####################################################################### 
# 
# 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_RS_12_0m
_database_code_depnum_ccdc_archive 'CCDC 1843786'
_audit_update_record             
;
2018-05-17 deposited with the CCDC.
2018-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H12 N2, C Br Cl3'
_chemical_formula_sum            'C7 H12 Br Cl3 N2'
_chemical_formula_weight         310.45

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_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'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.8771(3)
_cell_length_b                   16.4201(9)
_cell_length_c                   11.9239(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.625(2)
_cell_angle_gamma                90
_cell_volume                     1130.96(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9917
_cell_measurement_theta_min      3.0304
_cell_measurement_theta_max      36.3347

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    4.301
_shelx_estimated_absorpt_T_min   0.278
_shelx_estimated_absorpt_T_max   0.480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4983
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube X-ray source'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23547
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.029
_diffrn_reflns_theta_max         33.137
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4405
_reflns_number_gt                3439
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Apex3 v2016.9-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2016/6 (Sheldrick, 2015, 2016), 
SHELXLE Rev714 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The trichloro-bromo-methane molecules are disordered across a mirror plane 
and bromide atoms are 1:1 disordered with chloride atoms. Overlapping Br and 
Cl atoms were constrained to have identical ADPs, and all C-Cl bond distances 
were restrained to be similar.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+1.8115P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0069(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4405
_refine_ls_number_parameters     136
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0625
_refine_ls_wR_factor_gt          0.0562
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.116
_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
C1 C -0.1405(3) -0.04122(12) 0.15105(17) 0.0145(4) Uani 1 1 d . . . . .
H1A H -0.103335 -0.070366 0.084023 0.017 Uiso 1 1 calc R U . A 2
H1B H -0.311105 -0.038231 0.142511 0.017 Uiso 1 1 calc R U . A 2
C2 C -0.0392(3) -0.08867(12) 0.26152(17) 0.0152(4) Uani 1 1 d . . . . .
H2A H -0.166034 -0.105021 0.301069 0.018 Uiso 1 1 calc R U . B 2
H2B H 0.038754 -0.138679 0.241657 0.018 Uiso 1 1 calc R U . B 2
C3 C 0.2102(3) 0.03571(12) 0.16716(17) 0.0140(4) Uani 1 1 d . . . . .
H3A H 0.278977 0.090902 0.170858 0.017 Uiso 1 1 calc R U . C 2
H3B H 0.248716 0.007509 0.099697 0.017 Uiso 1 1 calc R U . C 2
C4 C 0.3125(3) -0.01231(13) 0.27685(18) 0.0152(4) Uani 1 1 d . . . . .
H4A H 0.394936 -0.061087 0.256280 0.018 Uiso 1 1 calc R U . D 2
H4B H 0.425715 0.022286 0.327344 0.018 Uiso 1 1 calc R U . D 2
C5 C -0.0953(3) 0.08380(12) 0.25695(17) 0.0156(4) Uani 1 1 d . . . . .
H5A H -0.265044 0.088734 0.250547 0.019 Uiso 1 1 calc R U . E 2
H5B H -0.028792 0.139366 0.261513 0.019 Uiso 1 1 calc R U . E 2
C6 C 0.0068(4) 0.03584(13) 0.36656(17) 0.0170(4) Uani 1 1 d . . . . .
H6A H 0.116183 0.070994 0.418256 0.020 Uiso 1 1 calc R U . F 2
H6B H -0.119418 0.019915 0.406789 0.020 Uiso 1 1 calc R U . F 2
C7 C 0.4761(4) 0.250000 0.4561(2) 0.0106(5) Uani 1 2 d DS T P . .
C8 C 0.5392(4) 0.250000 0.9472(2) 0.0105(5) Uani 1 2 d DS T P . .
Br1 Br 0.6414(4) 0.15563(17) 0.52765(19) 0.0100(2) Uani 0.5 1 d . . P G 1
Br2 Br 0.7104(3) 0.15765(14) 1.01943(13) 0.01061(19) Uani 0.5 1 d . . P H 1
Cl1 Cl 0.6237(11) 0.1599(4) 0.5122(5) 0.0100(2) Uani 0.5 1 d D . P G 2
Cl2 Cl 0.6883(8) 0.1591(4) 1.0009(4) 0.01061(19) Uani 0.5 1 d D . P H 2
Cl3 Cl 0.46069(12) 0.250000 0.30582(6) 0.01710(14) Uani 1 2 d DS T P G 2
Cl4 Cl 0.18989(11) 0.250000 0.48549(6) 0.01645(14) Uani 1 2 d DS T P G 2
Cl5 Cl 0.51679(12) 0.250000 0.79700(6) 0.01825(14) Uani 1 2 d DS T P H 2
Cl6 Cl 0.25563(11) 0.250000 0.98024(6) 0.01647(14) Uani 1 2 d DS T P H 2
N1 N -0.0432(3) 0.04212(10) 0.15562(14) 0.0124(3) Uani 1 1 d . . . I 2
N2 N 0.1281(3) -0.03748(10) 0.33790(14) 0.0113(3) Uani 1 1 d . . . J 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.480(2) . ?
C1 C2 1.552(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N2 1.474(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N1 1.473(2) . ?
C3 C4 1.551(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N2 1.472(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.469(3) . ?
C5 C6 1.549(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N2 1.471(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 Cl3 1.778(3) . ?
C7 Cl4 1.780(3) . ?
C7 Cl1 1.783(6) 4_565 ?
C7 Cl1 1.783(6) . ?
C7 Br1 1.941(3) 4_565 ?
C7 Br1 1.941(3) . ?
C8 Cl5 1.771(3) . ?
C8 Cl6 1.782(2) . ?
C8 Cl2 1.788(5) 4_565 ?
C8 Cl2 1.788(5) . ?
C8 Br2 1.933(2) . ?
C8 Br2 1.933(2) 4_565 ?

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
N1 C1 C2 110.34(15) . . ?
N1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
N2 C2 C1 110.25(15) . . ?
N2 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
N2 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
N1 C3 C4 110.07(15) . . ?
N1 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
N1 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.2 . . ?
N2 C4 C3 110.70(14) . . ?
N2 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
N1 C5 C6 110.50(15) . . ?
N1 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
N2 C6 C5 110.42(16) . . ?
N2 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
N2 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
Cl3 C7 Cl4 108.91(13) . . ?
Cl3 C7 Cl1 108.0(2) . . ?
Cl4 C7 Cl1 109.8(3) . . ?
Cl1 C7 Cl1 112.3(5) 4_565 . ?
Br1 C7 Br1 105.94(19) 4_565 . ?
Cl5 C8 Cl6 108.99(13) . . ?
Cl5 C8 Cl2 107.6(2) . 4_565 ?
Cl6 C8 Cl2 109.7(2) . 4_565 ?
Cl5 C8 Cl2 107.6(2) . . ?
Cl6 C8 Cl2 109.7(2) . . ?
Cl2 C8 Cl2 113.1(4) 4_565 . ?
Br2 C8 Br2 103.38(16) . 4_565 ?
C5 N1 C3 108.46(15) . . ?
C5 N1 C1 108.85(16) . . ?
C3 N1 C1 108.33(15) . . ?
C6 N2 C4 108.52(15) . . ?
C6 N2 C2 108.28(15) . . ?
C4 N2 C2 108.83(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 -1.1(2) . . . . ?
N1 C3 C4 N2 -0.1(2) . . . . ?
N1 C5 C6 N2 0.4(2) . . . . ?
C6 C5 N1 C3 -59.3(2) . . . . ?
C6 C5 N1 C1 58.35(19) . . . . ?
C4 C3 N1 C5 59.0(2) . . . . ?
C4 C3 N1 C1 -59.0(2) . . . . ?
C2 C1 N1 C5 -57.94(19) . . . . ?
C2 C1 N1 C3 59.8(2) . . . . ?
C5 C6 N2 C4 58.4(2) . . . . ?
C5 C6 N2 C2 -59.5(2) . . . . ?
C3 C4 N2 C6 -58.6(2) . . . . ?
C3 C4 N2 C2 59.0(2) . . . . ?
C1 C2 N2 C6 59.7(2) . . . . ?
C1 C2 N2 C4 -58.0(2) . . . . ?

_refine_diff_density_max         0.603
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.119



####################################################################### 
# 
# 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_RS_11_0m
_database_code_depnum_ccdc_archive 'CCDC 1843783'
_audit_update_record             
;
2018-05-17 deposited with the CCDC.
2018-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H12 N2, C H Br3'
_chemical_formula_sum            'C7 H13 Br3 N2'
_chemical_formula_weight         364.92

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'
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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.0754(3)
_cell_length_b                   15.7428(9)
_cell_length_c                   12.0401(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.8849(19)
_cell_angle_gamma                90
_cell_volume                     1126.88(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9987
_cell_measurement_theta_min      3.1125
_cell_measurement_theta_max      36.2822

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.151
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    10.694
_shelx_estimated_absorpt_T_min   0.154
_shelx_estimated_absorpt_T_max   0.446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4624
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube X-ray source'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21426
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.112
_diffrn_reflns_theta_max         36.376
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5336
_reflns_number_gt                3860
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Apex3 v2016.9-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2016/6 (Sheldrick, 2015, 2016), 
SHELXLE Rev714 (Hübschle et al., 2011)
;
_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)+(0.0131P)²+0.7095P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0032(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5336
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0511
_refine_ls_wR_factor_gt          0.0459
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
Br1 Br 0.83463(3) 0.16452(2) 0.56191(2) 0.01471(5) Uani 1 1 d . . . . .
C1 C 0.7435(3) 0.43741(12) 0.85586(16) 0.0171(4) Uani 1 1 d . . . . .
H1A H 0.581915 0.441035 0.858366 0.021 Uiso 1 1 calc R U . . .
H1B H 0.826841 0.419258 0.931633 0.021 Uiso 1 1 calc R U . . .
N1 N 0.8245(3) 0.52140(10) 0.82846(13) 0.0148(3) Uani 1 1 d . . . . .
Br2 Br 1.27655(3) 0.26270(2) 0.52940(2) 0.01927(5) Uani 1 1 d . . . . .
C2 C 0.7771(3) 0.37104(12) 0.76569(16) 0.0181(4) Uani 1 1 d . . . . .
H2A H 0.876633 0.324922 0.802686 0.022 Uiso 1 1 calc R U . . .
H2B H 0.630220 0.345717 0.730326 0.022 Uiso 1 1 calc R U . . .
N2 N 0.8780(3) 0.41161(10) 0.67740(13) 0.0153(3) Uani 1 1 d . . . . .
Br3 Br 0.81392(3) 0.29181(2) 0.35399(2) 0.02439(6) Uani 1 1 d . . . . .
C4 C 0.7287(4) 0.48055(13) 0.62513(16) 0.0223(4) Uani 1 1 d . . . . .
H4A H 0.579866 0.456872 0.589604 0.027 Uiso 1 1 calc R U . . .
H4B H 0.792842 0.508065 0.564986 0.027 Uiso 1 1 calc R U . . .
C5 C 1.0648(3) 0.51352(12) 0.82474(16) 0.0164(4) Uani 1 1 d . . . . .
H5A H 1.150391 0.494290 0.899538 0.020 Uiso 1 1 calc R U . . .
H5B H 1.124289 0.569608 0.808124 0.020 Uiso 1 1 calc R U . . .
C6 C 1.0959(3) 0.44885(13) 0.73186(17) 0.0198(4) Uani 1 1 d . . . . .
H6A H 1.163349 0.477827 0.673956 0.024 Uiso 1 1 calc R U . . .
H6B H 1.199665 0.403178 0.766466 0.024 Uiso 1 1 calc R U . . .
C7 C 0.9531(3) 0.26818(12) 0.51009(15) 0.0146(3) Uani 1 1 d . . . . .
H7 H 0.916068 0.316039 0.557705 0.018 Uiso 1 1 calc R U . . .
C3 C 0.7002(3) 0.54731(12) 0.71548(16) 0.0188(4) Uani 1 1 d . . . . .
H3A H 0.756662 0.603018 0.695305 0.023 Uiso 1 1 calc R U . . .
H3B H 0.538618 0.553598 0.716850 0.023 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C7 1.9378(18) . ?
C1 N1 1.472(2) . ?
C1 C2 1.550(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N1 C3 1.471(2) . ?
N1 C5 1.475(2) . ?
Br2 C7 1.9328(18) . ?
C2 N2 1.477(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N2 C4 1.470(2) . ?
N2 C6 1.473(2) . ?
Br3 C7 1.9316(18) . ?
C4 C3 1.548(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.552(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7 1.0000 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 110.49(14) . . ?
N1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
C3 N1 C1 108.94(15) . . ?
C3 N1 C5 108.57(14) . . ?
C1 N1 C5 108.06(15) . . ?
N2 C2 C1 110.28(15) . . ?
N2 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
N2 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C4 N2 C6 108.39(16) . . ?
C4 N2 C2 108.45(15) . . ?
C6 N2 C2 108.65(14) . . ?
N2 C4 C3 110.42(15) . . ?
N2 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
N2 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
N1 C5 C6 110.18(14) . . ?
N1 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
N2 C6 C5 110.52(15) . . ?
N2 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
Br3 C7 Br2 110.86(9) . . ?
Br3 C7 Br1 111.00(9) . . ?
Br2 C7 Br1 111.07(9) . . ?
Br3 C7 H7 107.9 . . ?
Br2 C7 H7 107.9 . . ?
Br1 C7 H7 107.9 . . ?
N1 C3 C4 110.55(15) . . ?
N1 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?

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
C2 C1 N1 C3 58.91(19) . . . . ?
C2 C1 N1 C5 -58.87(19) . . . . ?
N1 C1 C2 N2 -0.8(2) . . . . ?
C1 C2 N2 C4 -58.41(19) . . . . ?
C1 C2 N2 C6 59.20(19) . . . . ?
C6 N2 C4 C3 -57.9(2) . . . . ?
C2 N2 C4 C3 59.9(2) . . . . ?
C3 N1 C5 C6 -57.46(19) . . . . ?
C1 N1 C5 C6 60.55(19) . . . . ?
C4 N2 C6 C5 60.17(19) . . . . ?
C2 N2 C6 C5 -57.5(2) . . . . ?
N1 C5 C6 N2 -2.2(2) . . . . ?
C1 N1 C3 C4 -57.5(2) . . . . ?
C5 N1 C3 C4 59.9(2) . . . . ?
N2 C4 C3 N1 -1.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 N2 1.00 2.13 3.121(2) 171.6 .

_refine_diff_density_max         1.306
_refine_diff_density_min         -1.466
_refine_diff_density_rms         0.166



####################################################################### 
# 
# 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_RS_10B_0m
_database_code_depnum_ccdc_archive 'CCDC 1843784'
_audit_update_record             
;
2018-05-17 deposited with the CCDC.
2018-06-27 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT431_RS_10B_0m           
;
PROBLEM: Short Inter HL..A Contact  Br2      ..N2               2.73 Ang.
RESPONSE: Result of halogen bonding - a topic of this work
;
_vrf_PLAT431_RS_10B_0m_2         
;
PROBLEM: Short Inter HL..A Contact  Br3      ..N5               2.69 Ang.
RESPONSE: Result of halogen bonding - a topic of this work
;
_vrf_PLAT431_RS_10B_0m_3         
;
PROBLEM: Short Inter HL..A Contact  Br4      ..N1               2.74 Ang.
RESPONSE: Result of halogen bonding - a topic of this work
;
_vrf_PLAT431_RS_10B_0m_4         
;
PROBLEM: Short Inter HL..A Contact  Br9      ..N3               2.65 Ang.
RESPONSE: Result of halogen bonding - a topic of this work
;
# Added during the CSD deposition process: Thursday 17 May 2018 09:44 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H12 N2, C Br3 F'
_chemical_formula_sum            'C7 H12 Br3 F N2'
_chemical_formula_weight         382.92

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.5248(4)
_cell_length_b                   14.6823(8)
_cell_length_c                   19.4306(13)
_cell_angle_alpha                72.579(2)
_cell_angle_beta                 85.379(2)
_cell_angle_gamma                85.795(2)
_cell_volume                     1767.91(19)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9580
_cell_measurement_theta_min      3.0876
_cell_measurement_theta_max      36.3922

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.158
_exptl_crystal_F_000             1092
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.490
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    10.242
_shelx_estimated_absorpt_T_min   0.071
_shelx_estimated_absorpt_T_max   0.222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5534
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube X-ray source'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42132
_diffrn_reflns_av_unetI/netI     0.0802
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.793
_diffrn_reflns_theta_max         36.470
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             15837
_reflns_number_gt                10449
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Apex3 v2016.9-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2016/6 (Sheldrick, 2015, 2016), 
SHELXLE Rev714 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Two DABCO molecules are disordered around inversion centers. Their geometries 
were restrained to be similar to that of another not disordered DABCO molecule, 
and Uij components of ADPs were restrained to be similar to each other for atoms 
closer than 1.7 Angstrom.  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0202P)²+1.0467P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.00219(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         15837
_refine_ls_number_parameters     413
_refine_ls_number_restraints     63
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.0712
_refine_ls_wR_factor_gt          0.0656
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.046
_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
N1 N 0.2559(4) 0.60172(16) 0.36435(13) 0.0176(5) Uani 1 1 d . . . . .
C1 C 0.4110(5) 0.5776(2) 0.41862(17) 0.0222(6) Uani 1 1 d . . . . .
H1A H 0.485503 0.516397 0.418449 0.027 Uiso 1 1 calc R U . . .
H1B H 0.341932 0.569264 0.467211 0.027 Uiso 1 1 calc R U . . .
C2 C 0.5661(5) 0.6572(2) 0.40249(19) 0.0282(7) Uani 1 1 d . . . . .
H2A H 0.571326 0.679830 0.445453 0.034 Uiso 1 1 calc R U . . .
H2B H 0.705448 0.631588 0.391498 0.034 Uiso 1 1 calc R U . . .
C3 C 0.1426(5) 0.6901(2) 0.36751(18) 0.0247(7) Uani 1 1 d . . . . .
H3A H 0.063669 0.678982 0.414721 0.030 Uiso 1 1 calc R U . . .
H3B H 0.043587 0.709529 0.329074 0.030 Uiso 1 1 calc R U . . .
C4 C 0.2913(5) 0.7712(2) 0.35763(19) 0.0247(7) Uani 1 1 d . . . . .
H4A H 0.247609 0.827873 0.318131 0.030 Uiso 1 1 calc R U . . .
H4B H 0.287630 0.789973 0.402614 0.030 Uiso 1 1 calc R U . . .
C5 C 0.3637(6) 0.6172(2) 0.29333(17) 0.0298(8) Uani 1 1 d . . . . .
H5A H 0.262435 0.629271 0.255904 0.036 Uiso 1 1 calc R U . . .
H5B H 0.450234 0.559380 0.292121 0.036 Uiso 1 1 calc R U . . .
C6 C 0.5005(6) 0.7038(3) 0.27718(19) 0.0387(9) Uani 1 1 d . . . . .
H6A H 0.642767 0.684901 0.263057 0.046 Uiso 1 1 calc R U . . .
H6B H 0.447637 0.755930 0.236207 0.046 Uiso 1 1 calc R U . . .
N2 N 0.5025(4) 0.73793(17) 0.34014(13) 0.0205(5) Uani 1 1 d . . . . .
N3 N 0.3335(4) 0.32356(15) 0.09053(12) 0.0153(5) Uani 1 1 d D . . . .
C7 C 0.2768(5) 0.2528(2) 0.15993(15) 0.0208(6) Uani 1 1 d D . . . .
H7A H 0.302905 0.187476 0.155458 0.025 Uiso 1 1 calc R U . . .
H7B H 0.128208 0.261633 0.172651 0.025 Uiso 1 1 calc R U . . .
C8 C 0.4038(5) 0.2647(2) 0.22003(16) 0.0213(6) Uani 1 1 d D . . . .
H8A H 0.309779 0.277889 0.258900 0.026 Uiso 1 1 calc R U . . .
H8B H 0.485561 0.204609 0.241141 0.026 Uiso 1 1 calc R U . . .
C9 C 0.5555(5) 0.3100(2) 0.07328(17) 0.0240(6) Uani 1 1 d D . . . .
H9A H 0.595786 0.356935 0.026602 0.029 Uiso 1 1 calc R U . . .
H9B H 0.585963 0.245080 0.068494 0.029 Uiso 1 1 calc R U . . .
C10 C 0.6801(4) 0.3233(2) 0.13322(17) 0.0232(7) Uani 1 1 d D . . . .
H10A H 0.766671 0.264501 0.153553 0.028 Uiso 1 1 calc R U . . .
H10B H 0.772211 0.376727 0.112559 0.028 Uiso 1 1 calc R U . . .
C11 C 0.2928(5) 0.42016(19) 0.09834(16) 0.0206(6) Uani 1 1 d D . . . .
H11A H 0.144000 0.430657 0.109829 0.025 Uiso 1 1 calc R U . . .
H11B H 0.332041 0.468543 0.052286 0.025 Uiso 1 1 calc R U . . .
C12 C 0.4181(5) 0.4315(2) 0.15958(18) 0.0245(7) Uani 1 1 d D . . . .
H12A H 0.509310 0.485554 0.139960 0.029 Uiso 1 1 calc R U . . .
H12B H 0.322846 0.445949 0.197708 0.029 Uiso 1 1 calc R U . . .
N4 N 0.5423(4) 0.34348(16) 0.19072(13) 0.0187(5) Uani 1 1 d D . . . .
N5 N 0.350(2) 0.9823(9) 0.0529(8) 0.0155(8) Uani 0.5 1 d D . P A -1
C13 C 0.4294(10) 1.0777(4) 0.0424(3) 0.0245(14) Uani 0.5 1 d D . P A -1
H13A H 0.490907 1.078797 0.087064 0.029 Uiso 0.5 1 calc R U P A -1
H13B H 0.314318 1.126732 0.032762 0.029 Uiso 0.5 1 calc R U P A -1
C14 C 0.5931(11) 1.1013(4) -0.0214(3) 0.0285(15) Uani 0.5 1 d D . P A -1
H14A H 0.544639 1.158229 -0.059707 0.034 Uiso 0.5 1 calc R U P A -1
H14B H 0.722610 1.116229 -0.004733 0.034 Uiso 0.5 1 calc R U P A -1
C15 C 0.5239(8) 0.9109(4) 0.0692(3) 0.0186(12) Uani 0.5 1 d D . P A -1
H15A H 0.475655 0.846566 0.074865 0.022 Uiso 0.5 1 calc R U P A -1
H15B H 0.580076 0.910284 0.115161 0.022 Uiso 0.5 1 calc R U P A -1
C16 C 0.6952(9) 0.9352(4) 0.0073(3) 0.0261(14) Uani 0.5 1 d D . P A -1
H16A H 0.823332 0.947138 0.026541 0.031 Uiso 0.5 1 calc R U P A -1
H16B H 0.723753 0.880287 -0.012247 0.031 Uiso 0.5 1 calc R U P A -1
C17 C 0.2677(9) 0.9813(4) -0.0154(3) 0.0219(12) Uani 0.5 1 d D . P A -1
H17A H 0.153173 1.030246 -0.027819 0.026 Uiso 0.5 1 calc R U P A -1
H17B H 0.212992 0.918038 -0.009395 0.026 Uiso 0.5 1 calc R U P A -1
C18 C 0.4375(9) 1.0017(5) -0.0767(3) 0.0253(13) Uani 0.5 1 d D . P A -1
H18A H 0.459419 0.946319 -0.095995 0.030 Uiso 0.5 1 calc R U P A -1
H18B H 0.393782 1.058074 -0.116423 0.030 Uiso 0.5 1 calc R U P A -1
N5B N 0.632(2) 1.0201(9) -0.0507(8) 0.0155(8) Uani 0.5 1 d D . P A -1
N6 N 0.360(2) 1.0612(10) 0.4648(7) 0.0120(6) Uani 0.5 1 d D . P B -1
C19 C 0.3952(10) 0.9829(4) 0.4321(3) 0.0264(14) Uani 0.5 1 d D . P B -1
H19A H 0.444697 1.008836 0.380856 0.032 Uiso 0.5 1 calc R U P B -1
H19B H 0.264138 0.952240 0.433603 0.032 Uiso 0.5 1 calc R U P B -1
C20 C 0.5573(10) 0.9070(4) 0.4731(3) 0.0240(13) Uani 0.5 1 d D . P B -1
H20A H 0.493891 0.844644 0.493746 0.029 Uiso 0.5 1 calc R U P B -1
H20B H 0.673761 0.899110 0.439095 0.029 Uiso 0.5 1 calc R U P B -1
C21 C 0.5548(9) 1.1062(4) 0.4624(4) 0.0259(14) Uani 0.5 1 d D . P B -1
H21A H 0.533038 1.157211 0.486311 0.031 Uiso 0.5 1 calc R U P B -1
H21B H 0.602823 1.135924 0.411407 0.031 Uiso 0.5 1 calc R U P B -1
C22 C 0.7213(8) 1.0314(4) 0.5007(3) 0.0192(12) Uani 0.5 1 d D . P B -1
H22A H 0.837427 1.026809 0.465636 0.023 Uiso 0.5 1 calc R U P B -1
H22B H 0.775048 1.051806 0.539705 0.023 Uiso 0.5 1 calc R U P B -1
C23 C 0.2897(9) 1.0191(4) 0.5408(3) 0.0198(12) Uani 0.5 1 d D . P B -1
H23A H 0.161298 0.985949 0.543451 0.024 Uiso 0.5 1 calc R U P B -1
H23B H 0.259758 1.070429 0.564126 0.024 Uiso 0.5 1 calc R U P B -1
C24 C 0.4574(8) 0.9470(4) 0.5815(3) 0.0193(12) Uani 0.5 1 d D . P B -1
H24A H 0.504514 0.969316 0.620608 0.023 Uiso 0.5 1 calc R U P B -1
H24B H 0.398589 0.883824 0.603739 0.023 Uiso 0.5 1 calc R U P B -1
N6B N 0.633(2) 0.9380(10) 0.5313(7) 0.0120(6) Uani 0.5 1 d D . P B -1
C25 C 0.8707(5) 1.0106(2) 0.23416(16) 0.0250(7) Uani 1 1 d . . . . .
C26 C 0.8930(4) 0.32687(18) 0.39668(14) 0.0144(5) Uani 1 1 d . . . . .
C27 C 1.0051(4) 0.65595(18) 0.11220(15) 0.0148(5) Uani 1 1 d . . . . .
Br1 Br 0.99248(7) 1.06458(2) 0.29988(2) 0.04314(11) Uani 1 1 d . . . . .
Br2 Br 0.73102(5) 0.89535(2) 0.28489(2) 0.02004(7) Uani 1 1 d . . . . .
Br3 Br 1.07436(5) 0.98997(2) 0.16172(2) 0.01960(7) Uani 1 1 d . . . . .
Br4 Br 1.03545(4) 0.44239(2) 0.38674(2) 0.01667(6) Uani 1 1 d . . . . .
Br5 Br 0.75340(4) 0.33689(2) 0.31001(2) 0.01651(6) Uani 1 1 d . . . . .
Br6 Br 1.08276(4) 0.21508(2) 0.42040(2) 0.01424(6) Uani 1 1 d . . . . .
Br7 Br 0.89572(4) 0.55318(2) 0.19073(2) 0.01724(6) Uani 1 1 d . . . . .
Br8 Br 0.98973(5) 0.77306(2) 0.13848(2) 0.02098(7) Uani 1 1 d . . . . .
Br9 Br 0.86694(4) 0.67005(2) 0.02453(2) 0.01625(6) Uani 1 1 d . . . . .
F1 F 0.7257(3) 1.07720(12) 0.19991(10) 0.0367(5) Uani 1 1 d . . . . .
F2 F 0.7460(3) 0.31661(12) 0.45212(9) 0.0222(4) Uani 1 1 d . . . . .
F3 F 1.2085(2) 0.63339(11) 0.10065(9) 0.0196(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.459(4) . ?
N1 C3 1.461(4) . ?
N1 C1 1.469(4) . ?
C1 C2 1.547(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N2 1.481(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.549(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N2 1.476(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.546(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N2 1.456(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
N3 C9 1.473(4) . ?
N3 C7 1.474(4) . ?
N3 C11 1.474(3) . ?
C7 C8 1.542(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N4 1.468(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.538(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N4 1.464(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.552(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N4 1.467(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
N5 C17 1.474(13) . ?
N5 C15 1.474(13) . ?
N5 C13 1.481(13) . ?
C13 C14 1.543(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N5B 1.466(13) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.551(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N5B 1.467(13) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.536(8) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 N5B 1.473(13) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N6 C19 1.467(13) . ?
N6 C21 1.469(13) . ?
N6 C23 1.469(13) . ?
C19 C20 1.557(7) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 N6B 1.469(13) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.552(7) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 N6B 1.463(13) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.553(7) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 N6B 1.468(13) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 F1 1.367(4) . ?
C25 Br3 1.932(3) . ?
C25 Br2 1.936(3) . ?
C25 Br1 1.937(3) . ?
C26 F2 1.364(3) . ?
C26 Br5 1.941(3) . ?
C26 Br6 1.944(3) . ?
C26 Br4 1.945(3) . ?
C27 F3 1.361(3) . ?
C27 Br7 1.928(3) . ?
C27 Br8 1.929(3) . ?
C27 Br9 1.941(3) . ?

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
C5 N1 C3 109.2(2) . . ?
C5 N1 C1 107.9(2) . . ?
C3 N1 C1 108.6(2) . . ?
N1 C1 C2 110.7(2) . . ?
N1 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
N2 C2 C1 109.7(2) . . ?
N2 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 . . ?
N2 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
N1 C3 C4 110.9(2) . . ?
N1 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.0 . . ?
N2 C4 C3 109.5(2) . . ?
N2 C4 H4A 109.8 . . ?
C3 C4 H4A 109.8 . . ?
N2 C4 H4B 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
N1 C5 C6 109.9(2) . . ?
N1 C5 H5A 109.7 . . ?
C6 C5 H5A 109.7 . . ?
N1 C5 H5B 109.7 . . ?
C6 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
N2 C6 C5 111.0(3) . . ?
N2 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 N2 C4 108.7(3) . . ?
C6 N2 C2 108.9(3) . . ?
C4 N2 C2 107.9(2) . . ?
C9 N3 C7 108.7(2) . . ?
C9 N3 C11 108.5(2) . . ?
C7 N3 C11 108.7(2) . . ?
N3 C7 C8 110.1(2) . . ?
N3 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
N3 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N4 C8 C7 110.4(2) . . ?
N4 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
N4 C8 H8B 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
N3 C9 C10 110.2(2) . . ?
N3 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
N3 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
N4 C10 C9 110.5(2) . . ?
N4 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N3 C11 C12 109.9(2) . . ?
N3 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
N3 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
N4 C12 C11 110.2(2) . . ?
N4 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
N4 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C10 N4 C12 108.6(2) . . ?
C10 N4 C8 109.1(2) . . ?
C12 N4 C8 108.6(2) . . ?
C17 N5 C15 108.6(9) . . ?
C17 N5 C13 108.3(9) . . ?
C15 N5 C13 108.0(9) . . ?
N5 C13 C14 110.7(7) . . ?
N5 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
N5 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
N5B C14 C13 110.3(7) . . ?
N5B C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
N5B C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
N5 C15 C16 110.2(7) . . ?
N5 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
N5 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
N5B C16 C15 110.5(7) . . ?
N5B C16 H16A 109.5 . . ?
C15 C16 H16A 109.5 . . ?
N5B C16 H16B 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
N5 C17 C18 110.4(7) . . ?
N5 C17 H17A 109.6 . . ?
C18 C17 H17A 109.6 . . ?
N5 C17 H17B 109.6 . . ?
C18 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
N5B C18 C17 110.9(7) . . ?
N5B C18 H18A 109.5 . . ?
C17 C18 H18A 109.5 . . ?
N5B C18 H18B 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C14 N5B C16 109.1(10) . . ?
C14 N5B C18 108.0(9) . . ?
C16 N5B C18 108.5(9) . . ?
C19 N6 C21 109.1(10) . . ?
C19 N6 C23 107.4(9) . . ?
C21 N6 C23 108.5(9) . . ?
N6 C19 C20 110.8(7) . . ?
N6 C19 H19A 109.5 . . ?
C20 C19 H19A 109.5 . . ?
N6 C19 H19B 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
N6B C20 C19 109.6(7) . . ?
N6B C20 H20A 109.7 . . ?
C19 C20 H20A 109.7 . . ?
N6B C20 H20B 109.7 . . ?
C19 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
N6 C21 C22 110.8(7) . . ?
N6 C21 H21A 109.5 . . ?
C22 C21 H21A 109.5 . . ?
N6 C21 H21B 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
N6B C22 C21 109.9(7) . . ?
N6B C22 H22A 109.7 . . ?
C21 C22 H22A 109.7 . . ?
N6B C22 H22B 109.7 . . ?
C21 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
N6 C23 C24 110.4(7) . . ?
N6 C23 H23A 109.6 . . ?
C24 C23 H23A 109.6 . . ?
N6 C23 H23B 109.6 . . ?
C24 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
N6B C24 C23 110.1(7) . . ?
N6B C24 H24A 109.6 . . ?
C23 C24 H24A 109.6 . . ?
N6B C24 H24B 109.6 . . ?
C23 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
C22 N6B C24 108.8(9) . . ?
C22 N6B C20 109.5(9) . . ?
C24 N6B C20 108.3(9) . . ?
F1 C25 Br3 108.0(2) . . ?
F1 C25 Br2 107.5(2) . . ?
Br3 C25 Br2 111.94(14) . . ?
F1 C25 Br1 106.42(18) . . ?
Br3 C25 Br1 110.73(17) . . ?
Br2 C25 Br1 111.95(15) . . ?
F2 C26 Br5 107.31(17) . . ?
F2 C26 Br6 108.03(16) . . ?
Br5 C26 Br6 111.40(13) . . ?
F2 C26 Br4 108.30(17) . . ?
Br5 C26 Br4 110.96(12) . . ?
Br6 C26 Br4 110.69(13) . . ?
F3 C27 Br7 107.59(17) . . ?
F3 C27 Br8 106.77(17) . . ?
Br7 C27 Br8 110.62(14) . . ?
F3 C27 Br9 108.80(18) . . ?
Br7 C27 Br9 110.78(13) . . ?
Br8 C27 Br9 112.08(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 56.9(3) . . . . ?
C3 N1 C1 C2 -61.4(3) . . . . ?
N1 C1 C2 N2 4.4(4) . . . . ?
C5 N1 C3 C4 -62.0(3) . . . . ?
C1 N1 C3 C4 55.5(3) . . . . ?
N1 C3 C4 N2 6.0(4) . . . . ?
C3 N1 C5 C6 54.6(4) . . . . ?
C1 N1 C5 C6 -63.2(3) . . . . ?
N1 C5 C6 N2 6.8(4) . . . . ?
C5 C6 N2 C4 -62.6(4) . . . . ?
C5 C6 N2 C2 54.7(4) . . . . ?
C3 C4 N2 C6 55.0(3) . . . . ?
C3 C4 N2 C2 -62.9(3) . . . . ?
C1 C2 N2 C6 -60.7(3) . . . . ?
C1 C2 N2 C4 57.1(3) . . . . ?
C9 N3 C7 C8 58.4(3) . . . . ?
C11 N3 C7 C8 -59.5(3) . . . . ?
N3 C7 C8 N4 0.6(3) . . . . ?
C7 N3 C9 C10 -59.5(3) . . . . ?
C11 N3 C9 C10 58.5(3) . . . . ?
N3 C9 C10 N4 1.2(3) . . . . ?
C9 N3 C11 C12 -59.5(3) . . . . ?
C7 N3 C11 C12 58.5(3) . . . . ?
N3 C11 C12 N4 0.9(4) . . . . ?
C9 C10 N4 C12 -60.1(3) . . . . ?
C9 C10 N4 C8 58.1(3) . . . . ?
C11 C12 N4 C10 58.7(3) . . . . ?
C11 C12 N4 C8 -59.8(3) . . . . ?
C7 C8 N4 C10 -59.1(3) . . . . ?
C7 C8 N4 C12 59.1(3) . . . . ?
C17 N5 C13 C14 -56.6(11) . . . . ?
C15 N5 C13 C14 60.8(10) . . . . ?
N5 C13 C14 N5B -3.3(7) . . . . ?
C17 N5 C15 C16 59.8(10) . . . . ?
C13 N5 C15 C16 -57.4(10) . . . . ?
N5 C15 C16 N5B -2.0(7) . . . . ?
C15 N5 C17 C18 -57.5(10) . . . . ?
C13 N5 C17 C18 59.5(10) . . . . ?
N5 C17 C18 N5B -2.1(7) . . . . ?
C13 C14 N5B C16 -56.9(11) . . . . ?
C13 C14 N5B C18 60.8(10) . . . . ?
C15 C16 N5B C14 60.1(11) . . . . ?
C15 C16 N5B C18 -57.3(10) . . . . ?
C17 C18 N5B C14 -58.1(10) . . . . ?
C17 C18 N5B C16 60.0(10) . . . . ?
C21 N6 C19 C20 59.1(11) . . . . ?
C23 N6 C19 C20 -58.3(11) . . . . ?
N6 C19 C20 N6B -2.0(7) . . . . ?
C19 N6 C21 C22 -56.6(11) . . . . ?
C23 N6 C21 C22 60.1(11) . . . . ?
N6 C21 C22 N6B -2.6(7) . . . . ?
C19 N6 C23 C24 61.1(10) . . . . ?
C21 N6 C23 C24 -56.7(10) . . . . ?
N6 C23 C24 N6B -3.0(6) . . . . ?
C21 C22 N6B C24 -57.7(10) . . . . ?
C21 C22 N6B C20 60.6(11) . . . . ?
C23 C24 N6B C22 61.0(10) . . . . ?
C23 C24 N6B C20 -58.0(10) . . . . ?
C19 C20 N6B C22 -57.9(11) . . . . ?
C19 C20 N6B C24 60.6(10) . . . . ?

_refine_diff_density_max         2.111
_refine_diff_density_min         -1.944
_refine_diff_density_rms         0.183



