# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2022

####################################################################### 
# 
# 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_mz173
_database_code_depnum_ccdc_archive 'CCDC 2118170'
loop_
_audit_author_name
_audit_author_address
'Andrea Daolio'
;polytechnic of Milan
Italy
;
_audit_update_record             
;
2021-10-27 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;
_audit_creation_date             2021-10-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_chemical_name_common            ?
_chemical_name_systematic        'Hexamethonium Bromide Methanol solvate'
_chemical_formula_moiety         'C12 H30 N2 2+, C H4 O, 2Br 1-'
_chemical_formula_sum            'C13 H34 Br2 N2 O'
_chemical_formula_weight         394.24
_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 0.0033 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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.270(2)
_cell_length_b                   11.720(3)
_cell_length_c                   16.537(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.20(3)
_cell_angle_gamma                90.00
_cell_volume                     1795.3(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1410
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      23.06
_cell_measurement_theta_min      3.02
_exptl_absorpt_coefficient_mu    4.510
_exptl_absorpt_correction_T_max  0.7007
_exptl_absorpt_correction_T_min  0.4550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
Bruker KRYOFLEX low temperature device. 
The hexametonium dibromide was crystallized by isopropanol.
12345678901234567890123456789012345678901234567890123456789012345678901234567890
We obtained always very small needles. In a vial, after about a month we noticed
some bigger needles, possibly usefull to a data collection. We choose the larger
one, a lamina rather then a needle. Surprising the crystal contain methanol 
rather than isopropanol, 
;
_diffrn_reflns_av_R_equivalents  0.1308
_diffrn_reflns_av_unetI/netI     0.1329
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14875
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.13
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0.00
_reflns_number_gt                1749
_reflns_number_total             3154
_reflns_threshold_expression     I>2σ(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  
'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)'
_computing_structure_solution    
;
SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., 
Giacovazzo, C., Polidori, G. & Spagna, R. (2003). 
J. Appl. Cryst. 36, 1103.)
;
_refine_diff_density_max         1.392
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.136
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         3154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1293
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      0.953
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0432P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.1117
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
1.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
1.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.74526(7) 0.57281(6) 0.11468(4) 0.0236(2) Uani 1 1 d . . .
Br2 Br 0.28534(8) -0.05972(6) 0.11239(4) 0.0248(2) Uani 1 1 d . . .
N1 N 0.2053(6) 0.5732(5) 0.1140(3) 0.0202(13) Uani 1 1 d . . .
N2 N -0.1663(6) -0.0684(5) 0.1589(3) 0.0194(13) Uani 1 1 d . . .
C1 C 0.1322(8) 0.4584(6) 0.0990(4) 0.0237(18) Uani 1 1 d . . .
H1A H 0.1519 0.4336 0.0439 0.028 Uiso 1 1 calc R . .
H1B H 0.0277 0.4690 0.1018 0.028 Uiso 1 1 calc R . .
C2 C 0.1780(8) 0.3631(6) 0.1575(4) 0.0241(18) Uani 1 1 d . . .
H2A H 0.1571 0.3853 0.2129 0.029 Uiso 1 1 calc R . .
H2B H 0.2821 0.3499 0.1549 0.029 Uiso 1 1 calc R . .
C3 C 0.0948(8) 0.2523(6) 0.1344(4) 0.0260(19) Uani 1 1 d . . .
H3A H 0.0954 0.2421 0.0756 0.031 Uiso 1 1 calc R . .
H3B H 0.1452 0.1871 0.1595 0.031 Uiso 1 1 calc R . .
C4 C -0.0588(8) 0.2529(6) 0.1603(4) 0.0265(19) Uani 1 1 d . . .
H4A H -0.1062 0.3222 0.1393 0.032 Uiso 1 1 calc R . .
H4B H -0.0587 0.2564 0.2195 0.032 Uiso 1 1 calc R . .
C5 C -0.1484(8) 0.1481(6) 0.1315(4) 0.0222(18) Uani 1 1 d . . .
H5A H -0.2510 0.1607 0.1408 0.027 Uiso 1 1 calc R . .
H5B H -0.1373 0.1357 0.0734 0.027 Uiso 1 1 calc R . .
C6 C -0.0932(7) 0.0437(6) 0.1796(4) 0.0239(18) Uani 1 1 d . . .
H6A H 0.0103 0.0354 0.1712 0.029 Uiso 1 1 calc R . .
H6B H -0.1046 0.0589 0.2373 0.029 Uiso 1 1 calc R . .
C7 C 0.3639(8) 0.5659(6) 0.1087(4) 0.0297(18) Uani 1 1 d . . .
H7A H 0.4057 0.6412 0.1161 0.045 Uiso 1 1 calc R . .
H7B H 0.3876 0.5365 0.0560 0.045 Uiso 1 1 calc R . .
H7C H 0.4024 0.5152 0.1506 0.045 Uiso 1 1 calc R . .
C8 C 0.1471(8) 0.6521(6) 0.0494(4) 0.0261(19) Uani 1 1 d . . .
H8A H 0.0429 0.6564 0.0520 0.039 Uiso 1 1 calc R . .
H8B H 0.1724 0.6235 -0.0032 0.039 Uiso 1 1 calc R . .
H8C H 0.1883 0.7275 0.0577 0.039 Uiso 1 1 calc R . .
C9 C 0.1648(8) 0.6209(6) 0.1944(4) 0.0281(19) Uani 1 1 d . . .
H9A H 0.2020 0.5716 0.2374 0.042 Uiso 1 1 calc R . .
H9B H 0.0605 0.6253 0.1964 0.042 Uiso 1 1 calc R . .
H9C H 0.2057 0.6966 0.2012 0.042 Uiso 1 1 calc R . .
C10 C -0.1272(8) -0.1086(6) 0.0760(4) 0.0266(19) Uani 1 1 d . . .
H10A H -0.1700 -0.0579 0.0353 0.040 Uiso 1 1 calc R . .
H10B H -0.1633 -0.1854 0.0671 0.040 Uiso 1 1 calc R . .
H10C H -0.0230 -0.1082 0.0721 0.040 Uiso 1 1 calc R . .
C11 C -0.1110(8) -0.1529(6) 0.2196(4) 0.0277(19) Uani 1 1 d . . .
H11A H -0.0063 -0.1529 0.2210 0.042 Uiso 1 1 calc R . .
H11B H -0.1464 -0.2283 0.2049 0.042 Uiso 1 1 calc R . .
H11C H -0.1444 -0.1326 0.2726 0.042 Uiso 1 1 calc R . .
C12 C -0.3266(7) -0.0614(7) 0.1620(4) 0.0252(17) Uani 1 1 d . . .
H12A H -0.3531 -0.0394 0.2160 0.038 Uiso 1 1 calc R . .
H12B H -0.3684 -0.1353 0.1487 0.038 Uiso 1 1 calc R . .
H12C H -0.3627 -0.0051 0.1233 0.038 Uiso 1 1 calc R . .
C13 C 0.4884(8) 0.2366(7) 0.0575(4) 0.037(2) Uani 1 1 d . . .
H13A H 0.3951 0.2577 0.0334 0.055 Uiso 1 1 calc R . .
H13B H 0.5353 0.1829 0.0224 0.055 Uiso 1 1 calc R . .
H13C H 0.5479 0.3043 0.0642 0.055 Uiso 1 1 calc R . .
O1 O 0.4689(6) 0.1849(4) 0.1349(3) 0.0308(13) Uani 1 1 d . . .
H1 H 0.4183 0.1268 0.1291 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 C1 1.522(8) . ?
N1 C7 1.479(8) . ?
N1 C8 1.497(8) . ?
N1 C9 1.503(8) . ?
N2 C6 1.511(8) . ?
N2 C10 1.508(8) . ?
N2 C11 1.487(8) . ?
N2 C12 1.491(8) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 C2 1.526(9) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 C3 1.551(9) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 C4 1.503(9) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 C5 1.548(9) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 C6 1.537(9) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C13 O1 1.435(7) . ?
O1 H1 0.8300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C1 112.1(6) . . ?
C7 N1 C8 109.0(5) . . ?
C7 N1 C9 110.9(5) . . ?
C8 N1 C1 106.5(5) . . ?
C8 N1 C9 107.8(5) . . ?
C9 N1 C1 110.3(5) . . ?
C10 N2 C6 110.9(5) . . ?
C11 N2 C6 106.7(5) . . ?
C11 N2 C10 108.5(5) . . ?
C11 N2 C12 109.3(5) . . ?
C12 N2 C6 112.5(5) . . ?
C12 N2 C10 108.8(5) . . ?
N1 C1 H1A 108.4 . . ?
N1 C1 H1B 108.4 . . ?
N1 C1 C2 115.7(6) . . ?
H1A C1 H1B 107.4 . . ?
C2 C1 H1A 108.4 . . ?
C2 C1 H1B 108.4 . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
C1 C2 C3 109.5(6) . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 C2 113.2(6) . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C3 C4 C5 114.3(6) . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C4 C5 H5A 110.1 . . ?
C4 C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?
C6 C5 C4 107.9(6) . . ?
C6 C5 H5A 110.1 . . ?
C6 C5 H5B 110.1 . . ?
N2 C6 C5 115.9(6) . . ?
N2 C6 H6A 108.3 . . ?
N2 C6 H6B 108.3 . . ?
C5 C6 H6A 108.3 . . ?
C5 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
C13 O1 H1 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -179.9(6) . . . . ?
C1 C2 C3 C4 -76.8(7) . . . . ?
C2 C3 C4 C5 174.9(6) . . . . ?
C3 C4 C5 C6 70.9(7) . . . . ?
C4 C5 C6 N2 -179.0(6) . . . . ?
C7 N1 C1 C2 59.7(7) . . . . ?
C8 N1 C1 C2 178.9(6) . . . . ?
C9 N1 C1 C2 -64.4(7) . . . . ?
C10 N2 C6 C5 69.7(7) . . . . ?
C11 N2 C6 C5 -172.4(5) . . . . ?
C12 N2 C6 C5 -52.5(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ljl033
_database_code_depnum_ccdc_archive 'CCDC 2119855'
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;
_audit_creation_date             2021-10-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
# ========
# Chemical
# ========
_chemical_name_common            ljl033
_chemical_formula_moiety         'C12 H30 N2, C2 H3 N, 2(I)'
_chemical_formula_sum            'C14 H33 I2 N3'
_chemical_formula_weight         497.2472
_chemical_absolute_configuration unk
_chemical_compound_source        'see text'
# ==========
# Atom types
# ==========
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction (B3LYP).'
H H 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction (B3LYP).'
N N 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction (B3LYP).'
I I 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction (B3LYP).'

# ========
# Symmetry
# ========
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-p 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 '+x, +y, +z'
2 '-x, -y, -z'
3 '-x+1/2, +y+1/2, -z+1/2'
4 '+x+1/2, -y+1/2, +z+1/2'

_symmetry_Int_Tables_number      14
_cell_length_a                   9.920(2)
_cell_length_b                   12.776(2)
_cell_length_c                   16.440(3)
_cell_angle_alpha                90.000000(0)
_cell_angle_beta                 96.07(2)
_cell_angle_gamma                90.000000(0)
_cell_volume                     2071.9(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4663
# =========
# Unit cell
# =========
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      28.08
_cell_measurement_theta_min      2.80
# ==============
# Absortion data
# ==============
_exptl_absorpt_coefficient_mu    3.031
_exptl_absorpt_correction_T_max  0.7149
_exptl_absorpt_correction_T_min  0.6308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# =======
# Crystal
# =======
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
Bruker KRYOFLEX low temperature device. 
;
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21599
_diffrn_reflns_theta_full        28.50
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         2.02
# ===========
# Reflections
# ===========
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0.00
_reflns_d_resolution_high        10.066527
_reflns_d_resolution_low         0.700291
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                4547
_reflns_number_total             4547
_reflns_threshold_expression     'F>0 & F/u(F)>3.0 & |F_calc|>10^-3'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_diff_density_max         1.1525
_refine_diff_density_min         -0.8440
_refine_diff_density_rms         0.1365
_refine_ls_coordinate_system     cartesian
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.2201
_refine_ls_goodness_of_fit_gt    1.2201
_refine_ls_hydrogen_treatment    refall
# ===============
# Refinement data
# ===============
_refine_ls_kind                  'Hirshfeld atom refinement (HAR)'
_refine_ls_matrix_type           full
_refine_ls_method_description    
;
   S.C. Capelli, H.-B. Burgi, B. Dittrich, S.Grabowsky
   and Dylan Jayatilaka, IUCrJ (2014). 1, 361-379
;
_refine_ls_number_constraints    165
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4547
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0404
_refine_ls_R_Fsqd_factor         0.0458
_refine_ls_shift/su_conv_tol     0.0100
_refine_ls_shift/su_max          0.0043
_refine_ls_shift/su_max_mean     0.0005
_refine_ls_shift/su_max_par      'H4A Uyy'
_refine_ls_structure_factor_coeff F
_refine_ls_SVD_threshold         0.1E-02
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.0235
_refine_ls_wR_factor_gt          0.0235
_refine_QCr_Psi_constraint       none
_refine_special_details          
;
  .  Hirshfeld atom refinement:
     .  Uses aspherical atomic scattering factors
        obtained from Hirshfeld partitioning of a
        gaussian quantum chemical wavefunction.
     .  Hirshfeld weight functions obtained from
        spherically averaged restricted atomic
        densities.
  .  Wavefunction type : B3LYP using cluster charges,
                        radius=8.0 angstrom
  .  Gaussian basis set: DGDZVP
  .  Refinement based on |F| with weight=1/sigma(|F|)
  .  Negative |F|^^2 were pruned from the data
  .  |F| < 3.0 sigma(|F|) were pruned from the data
  .  Eigenvalues < 0.1E-04 removed from normal equations
  . If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   HAR
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
# ======================
# Fractional coordinates
# ======================
loop_
_atom_site_label
_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_disorder_group
I1 0.73146(2) 0.079322(18) 0.121681(13) 0.02193(13) Uani 1.000000 .
I2 0.23892(2) 0.375005(18) 0.111418(13) 0.02364(13) Uani 1.000000 .
N1 0.7713(3) 0.4227(2) 0.12809(16) 0.0240(17) Uani 1.000000 .
N2 1.2042(3) 1.0352(2) 0.14023(16) 0.0193(16) Uani 1.000000 .
C1 0.7828(4) 0.5408(3) 0.1327(2) 0.025(2) Uani 1.000000 .
H1A 0.745(4) 0.562(3) 0.192(2) 0.049(12) Uiso 1.000000 .
H1B 0.713(4) 0.569(3) 0.081(2) 0.045(12) Uiso 1.000000 .
C2 0.9242(4) 0.5843(3) 0.1285(2) 0.028(2) Uani 1.000000 .
H2A 0.952(4) 0.565(4) 0.069(3) 0.078(16) Uiso 1.000000 .
H2B 0.998(4) 0.550(3) 0.174(2) 0.063(14) Uiso 1.000000 .
C3 0.9222(4) 0.7023(3) 0.1429(2) 0.027(2) Uani 1.000000 .
H3A 0.864(5) 0.743(4) 0.099(3) 0.079(16) Uiso 1.000000 .
H3B 0.903(5) 0.724(4) 0.208(3) 0.11(2) Uiso 1.000000 .
C4 1.0587(4) 0.7537(3) 0.1352(3) 0.029(2) Uani 1.000000 .
H4A 1.084(4) 0.742(3) 0.069(3) 0.076(16) Uiso 1.000000 .
H4B 1.125(5) 0.715(4) 0.172(3) 0.091(18) Uiso 1.000000 .
C5 1.0581(4) 0.8717(3) 0.1484(2) 0.025(2) Uani 1.000000 .
H5A 0.978(4) 0.911(3) 0.107(2) 0.065(14) Uiso 1.000000 .
H5B 1.031(4) 0.886(3) 0.210(2) 0.050(12) Uiso 1.000000 .
C6 1.1969(4) 0.9172(3) 0.1407(2) 0.023(2) Uani 1.000000 .
H6A 1.231(4) 0.894(3) 0.082(2) 0.057(13) Uiso 1.000000 .
H6B 1.265(3) 0.895(3) 0.191(2) 0.032(10) Uiso 1.000000 .
C7 1.3510(4) 1.0640(3) 0.1412(3) 0.030(2) Uani 1.000000 .
H7A 1.395(5) 1.023(4) 0.093(3) 0.079(17) Uiso 1.000000 .
H7B 1.355(4) 1.152(3) 0.139(2) 0.047(13) Uiso 1.000000 .
H7C 1.407(4) 1.031(3) 0.201(3) 0.066(14) Uiso 1.000000 .
C8 1.1506(4) 1.0832(3) 0.2134(2) 0.025(2) Uani 1.000000 .
H8A 1.196(4) 1.045(3) 0.264(2) 0.042(11) Uiso 1.000000 .
H8B 1.163(3) 1.169(3) 0.2100(19) 0.027(10) Uiso 1.000000 .
H8C 1.042(4) 1.069(3) 0.210(2) 0.044(12) Uiso 1.000000 .
C9 1.1280(4) 1.0794(3) 0.0644(2) 0.023(2) Uani 1.000000 .
H9A 1.171(4) 1.041(3) 0.011(2) 0.045(12) Uiso 1.000000 .
H9B 1.021(4) 1.067(3) 0.066(2) 0.030(10) Uiso 1.000000 .
H9C 1.147(3) 1.164(3) 0.066(2) 0.029(10) Uiso 1.000000 .
C10 0.8523(5) 0.3719(3) 0.2001(2) 0.032(2) Uani 1.000000 .
H10A 0.825(4) 0.412(3) 0.256(2) 0.058(14) Uiso 1.000000 .
H10B 0.828(4) 0.291(3) 0.194(2) 0.042(12) Uiso 1.000000 .
H10C 0.961(5) 0.389(4) 0.198(3) 0.079(17) Uiso 1.000000 .
C11 0.6241(4) 0.3965(4) 0.1297(3) 0.040(3) Uani 1.000000 .
H11A 0.603(5) 0.425(4) 0.183(3) 0.081(17) Uiso 1.000000 .
H11B 0.564(5) 0.436(4) 0.071(3) 0.078(17) Uiso 1.000000 .
H11C 0.618(4) 0.312(3) 0.130(2) 0.048(13) Uiso 1.000000 .
C12 0.8161(5) 0.3809(3) 0.0506(2) 0.030(2) Uani 1.000000 .
H12A 0.923(4) 0.391(3) 0.053(3) 0.062(15) Uiso 1.000000 .
H12B 0.805(4) 0.297(3) 0.049(2) 0.060(14) Uiso 1.000000 .
H12C 0.756(4) 0.420(3) -0.003(2) 0.036(11) Uiso 1.000000 .
N3 0.5404(5) 0.2985(4) 0.8512(3) 0.083(4) Uani 1.000000 .
C13 0.4948(4) 0.2517(3) 0.8999(2) 0.037(3) Uani 1.000000 .
C14 0.4376(5) 0.1934(3) 0.9622(2) 0.032(3) Uani 1.000000 .
H14A 0.519(4) 0.165(3) 1.005(3) 0.060(14) Uiso 1.000000 .
H14B 0.378(5) 0.131(4) 0.934(3) 0.084(18) Uiso 1.000000 .
H14C 0.370(5) 0.247(4) 0.995(3) 0.064(15) Uiso 1.000000 .

# ====
# ADPs
# ====

# ============
# Bond lengths
# ============
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C1 . 1.514(4) yes
N1 . C10 . 1.506(5) yes
N1 . C11 . 1.501(5) yes
N1 . C12 . 1.491(4) yes
N2 . C6 . 1.509(4) yes
N2 . C7 . 1.501(5) yes
N2 . C8 . 1.496(4) yes
N2 . C9 . 1.499(4) yes
C1 . H1A . 1.11(4) yes
C1 . H1B . 1.10(4) yes
C1 . C2 . 1.517(5) yes
C2 . H2A . 1.07(4) yes
C2 . H2B . 1.08(4) yes
C2 . C3 . 1.527(5) yes
C3 . H3A . 1.01(4) yes
C3 . H3B . 1.14(5) yes
C3 . C4 . 1.522(5) yes
C4 . H4A . 1.16(5) yes
C4 . H4B . 0.98(4) yes
C4 . C5 . 1.522(5) yes
C5 . H5A . 1.11(4) yes
C5 . H5B . 1.09(4) yes
C5 . C6 . 1.512(5) yes
C6 . H6A . 1.10(4) yes
C6 . H6B . 1.05(3) yes
C7 . H7A . 1.08(5) yes
C7 . H7B . 1.13(4) yes
C7 . H7C . 1.15(4) yes
C8 . H8A . 1.03(3) yes
C8 . H8B . 1.11(4) yes
C8 . H8C . 1.09(4) yes
C9 . H9A . 1.12(4) yes
C9 . H9B . 1.07(3) yes
C9 . H9C . 1.10(4) yes
C10 . H10A . 1.11(4) yes
C10 . H10B . 1.07(4) yes
C10 . H10C . 1.10(5) yes
C11 . H11A . 0.99(5) yes
C11 . H11B . 1.19(4) yes
C11 . H11C . 1.09(4) yes
C12 . H12A . 1.07(4) yes
C12 . H12B . 1.08(4) yes
C12 . H12C . 1.13(3) yes
N3 . C13 . 1.131(5) yes
C13 . C14 . 1.432(5) yes
C14 . H14A . 1.07(4) yes
C14 . H14B . 1.07(5) yes
C14 . H14C . 1.14(5) yes

# ===========
# Bond Angles
# ===========
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 . N1 . C10 . 111.0(3) yes
C1 . N1 . C11 . 106.8(3) yes
C1 . N1 . C12 . 111.8(3) yes
C10 . N1 . C11 . 109.2(3) yes
C10 . N1 . C12 . 109.6(3) yes
C11 . N1 . C12 . 108.3(3) yes
C6 . N2 . C7 . 107.0(3) yes
C6 . N2 . C8 . 112.6(3) yes
C6 . N2 . C9 . 111.2(3) yes
C7 . N2 . C8 . 108.5(3) yes
C7 . N2 . C9 . 108.6(3) yes
C8 . N2 . C9 . 108.9(3) yes
N1 . C1 . H1A . 105(2) yes
N1 . C1 . H1B . 104.5(19) yes
N1 . C1 . C2 . 115.3(3) yes
H1A . C1 . H1B . 111(3) yes
C2 . C1 . H1A . 111(2) yes
C2 . C1 . H1B . 111(2) yes
C1 . C2 . H2A . 107(2) yes
C1 . C2 . H2B . 113(2) yes
C1 . C2 . C3 . 109.2(3) yes
H2A . C2 . H2B . 109(3) yes
C3 . C2 . H2A . 112(3) yes
C3 . C2 . H2B . 108(2) yes
C2 . C3 . H3A . 115(3) yes
C2 . C3 . H3B . 113(3) yes
C2 . C3 . C4 . 112.8(3) yes
H3A . C3 . H3B . 113(3) yes
C4 . C3 . H3A . 99(3) yes
C4 . C3 . H3B . 102(3) yes
C3 . C4 . H4A . 108(2) yes
C3 . C4 . H4B . 106(3) yes
C3 . C4 . C5 . 113.5(3) yes
H4A . C4 . H4B . 108(3) yes
C5 . C4 . H4A . 106(2) yes
C5 . C4 . H4B . 115(3) yes
C4 . C5 . H5A . 112(2) yes
C4 . C5 . H5B . 108(2) yes
C4 . C5 . C6 . 110.6(3) yes
H5A . C5 . H5B . 105(3) yes
C6 . C5 . H5A . 112(2) yes
C6 . C5 . H5B . 109(2) yes
N2 . C6 . C5 . 115.4(3) yes
N2 . C6 . H6A . 104(2) yes
N2 . C6 . H6B . 104.5(18) yes
C5 . C6 . H6A . 110(2) yes
C5 . C6 . H6B . 109.8(19) yes
H6A . C6 . H6B . 113(3) yes
N2 . C7 . H7A . 110(2) yes
N2 . C7 . H7B . 107(2) yes
N2 . C7 . H7C . 107(2) yes
H7A . C7 . H7B . 116(3) yes
H7A . C7 . H7C . 104(3) yes
H7B . C7 . H7C . 112(3) yes
N2 . C8 . H8A . 107(2) yes
N2 . C8 . H8B . 108.5(18) yes
N2 . C8 . H8C . 109(2) yes
H8A . C8 . H8B . 118(3) yes
H8A . C8 . H8C . 108(3) yes
H8B . C8 . H8C . 106(3) yes
N2 . C9 . H9A . 106.4(19) yes
N2 . C9 . H9B . 109.4(18) yes
N2 . C9 . H9C . 106.5(17) yes
H9A . C9 . H9B . 114(3) yes
H9A . C9 . H9C . 111(3) yes
H9B . C9 . H9C . 109(3) yes
N1 . C10 . H10A . 107(2) yes
N1 . C10 . H10B . 104.1(19) yes
N1 . C10 . H10C . 110(2) yes
H10A . C10 . H10B . 117(3) yes
H10A . C10 . H10C . 105(3) yes
H10B . C10 . H10C . 114(3) yes
N1 . C11 . H11A . 103(3) yes
N1 . C11 . H11B . 107(2) yes
N1 . C11 . H11C . 106(2) yes
H11A . C11 . H11B . 115(4) yes
H11A . C11 . H11C . 111(3) yes
H11B . C11 . H11C . 114(3) yes
N1 . C12 . H12A . 108(2) yes
N1 . C12 . H12B . 109(2) yes
N1 . C12 . H12C . 109.7(19) yes
H12A . C12 . H12B . 103(3) yes
H12A . C12 . H12C . 114(3) yes
H12B . C12 . H12C . 112(3) yes
N3 . C13 . C14 . 179.4(5) yes
C13 . C14 . H14A . 108(2) yes
C13 . C14 . H14B . 109(3) yes
C13 . C14 . H14C . 109(2) yes
H14A . C14 . H14B . 112(3) yes
H14A . C14 . H14C . 110(3) yes
H14B . C14 . H14C . 109(3) yes

_shelx_F_calc_maximum            538.041521
# ================
# Instruction file
# ================
_olex2_submission_special_instructions 'No special instructions were received'
_QCr_Becke_grid_accuracy         high
_QCr_Becke_grid_basis_fn_cutoff  .1E-09
_QCr_Becke_grid_core_pruning_scheme treutler_ahlrichs
_QCr_Becke_grid_H_pts_per_n_shell 5
_QCr_Becke_grid_kind             mura_knowles
_QCr_Becke_grid_L_angular_grid   35
_QCr_Becke_grid_L_H_angular_grid 29
_QCr_Becke_grid_n_pts_for_row_1  5890
_QCr_Becke_grid_n_pts_for_row_2  9212
_QCr_Becke_grid_n_pts_for_row_3  10542
_QCr_Becke_grid_n_radial_H_pts   35
_QCr_Becke_grid_reduce_L_H_ang_grid T
_QCr_Becke_grid_rho_cutoff       .1E-05
_QCr_Becke_grid_scale_H-He_grid  T
_QCr_calc_basis_max_l            2
_QCr_calc_gaussian_basis_set     DGDZVP
_QCr_calc_gaussian_basis_set_kind cartesian
# ==========
# QCr method
# ==========
_QCr_calc_method                 'Kohn-Sham/b3lypgxb3lypgc/SCCF L=1 R=8.0 A'
_QCr_calc_spinorbital_kind       restricted
_QCr_calc_unit                   'See _atom_site_* in tonto.cif2'
_QCr_calc_unit_n_alpha_electrons 122
_QCr_calc_unit_n_beta_electrons  122
_QCr_calc_unit_n_electrons       244
_QCr_calc_unit_spin_multiplicity 1
# ============
# QCr software
# ============
_QCr_software                    Tonto
_QCr_software_build_date         '2019-12-17 16:54'
_QCr_software_platform           Linux-4.15.0-72-generic
_QCr_software_version            '19.12.17 v. dd352d58'
_QCr_software_website            https://github.com/dylan-jayatilaka/tonto
####################################################################### 
# 
# 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_ljl043
_database_code_depnum_ccdc_archive 'CCDC 952025'
loop_
_audit_author_name
_audit_author_address
'Andrea Daolio'
;polytechnic of Milan
Italy
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;
_audit_creation_date             2021-10-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H30 N2 2+, C H3 N, 2(Br 1-)'
_chemical_formula_sum            'C14 H33 Br2 N3'
_chemical_formula_weight         403.25
_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 0.0033 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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   12.4309(10)
_cell_length_b                   9.5074(8)
_cell_length_c                   15.9984(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.584(5)
_cell_angle_gamma                90.00
_cell_volume                     1884.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4865
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      31.41
_cell_measurement_theta_min      2.49
_exptl_absorpt_coefficient_mu    4.296
_exptl_absorpt_correction_T_max  0.219122
_exptl_absorpt_correction_T_min  0.126343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
The crystals are needles nearly perfect in the mother solution. In
polarized light, instead, they show clearly polysynthetic twinning, parallel to the main axis of the needle. Morever, they are very fragile and when
extracted from the solution, they recrystallyze in a few seconds, losing 
acetonitrile. The crystal used in data collection was a bit too long, but it
did not request to be cut. The crystal was put in a drop of FOMBLIN,
immediately transferred on a glass fiber, and put into a cold nitrogen stream
at -170 ï>0C produced by a Bruker KRYOFLEX low temperature device.
The crystal was a two-component twin, clearly identified by the
software CELL_NOW (Bruker AXS). 
;
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            44615
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         34.72
_diffrn_reflns_theta_min         2.49
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.833
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0.00
_reflns_number_gt                5410
_reflns_number_total             6920
_reflns_threshold_expression     I>2σ(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  
'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)'
_computing_structure_solution    
;
SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., 
Giacovazzo, C., Polidori, G. & Spagna, R. (2003). 
J. Appl. Cryst. 36, 1103.)
;
_refine_diff_density_max         0.961
_refine_diff_density_min         -1.410
_refine_diff_density_rms         0.260
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         6920
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0950P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1438
_refine_ls_wR_factor_ref         0.1519
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
The ratio between the two components of the twin was 0.580/0.420
;
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C6(H6A,H6B), C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B), C3(H3A,H3B)
1.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C),
 C9(H9A,H9B,H9C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.08372(3) 0.27955(5) 0.10989(2) 0.01572(10) Uani 1 1 d . . .
Br2 Br 0.39008(4) 0.77678(5) 0.12109(2) 0.01789(10) Uani 1 1 d . . .
N1 N 0.4277(3) 0.2462(3) 0.1211(2) 0.0108(6) Uani 1 1 d . . .
N2 N 1.0642(3) -0.1851(3) 0.15355(19) 0.0114(6) Uani 1 1 d . . .
C1 C 0.5487(4) 0.2368(4) 0.1231(3) 0.0153(7) Uani 1 1 d . . .
H1A H 0.5802 0.3063 0.1642 0.018 Uiso 1 1 calc R . .
H1B H 0.5710 0.2638 0.0673 0.018 Uiso 1 1 calc R . .
C6 C 0.7132(3) 0.0880(4) 0.1259(2) 0.0147(7) Uani 1 1 d . . .
H6A H 0.7516 0.1695 0.1528 0.018 Uiso 1 1 calc R . .
H6B H 0.7165 0.0974 0.0645 0.018 Uiso 1 1 calc R . .
C2 C 0.5963(3) 0.0926(4) 0.1458(3) 0.0163(7) Uani 1 1 d . . .
H2A H 0.5913 0.0742 0.2063 0.020 Uiso 1 1 calc R . .
H2B H 0.5549 0.0188 0.1137 0.020 Uiso 1 1 calc R . .
C4 C 0.8872(3) -0.0507(4) 0.1276(2) 0.0148(7) Uani 1 1 d . . .
H4A H 0.8855 -0.0417 0.0659 0.018 Uiso 1 1 calc R . .
H4B H 0.9291 0.0292 0.1530 0.018 Uiso 1 1 calc R . .
C5 C 0.9417(3) -0.1880(4) 0.1548(2) 0.0145(7) Uani 1 1 d . . .
H5A H 0.9126 -0.2641 0.1173 0.017 Uiso 1 1 calc R . .
H5B H 0.9232 -0.2106 0.2123 0.017 Uiso 1 1 calc R . .
C11 C 1.1025(4) -0.3324(5) 0.1647(3) 0.0202(8) Uani 1 1 d . . .
H11A H 1.0702 -0.3905 0.1187 0.030 Uiso 1 1 calc R . .
H11B H 1.0812 -0.3690 0.2182 0.030 Uiso 1 1 calc R . .
H11C H 1.1813 -0.3350 0.1645 0.030 Uiso 1 1 calc R . .
C7 C 0.3749(4) 0.1688(5) 0.0465(2) 0.0187(8) Uani 1 1 d . . .
H7A H 0.4019 0.2058 -0.0050 0.028 Uiso 1 1 calc R . .
H7B H 0.2965 0.1818 0.0444 0.028 Uiso 1 1 calc R . .
H7C H 0.3918 0.0683 0.0515 0.028 Uiso 1 1 calc R . .
C8 C 0.3989(4) 0.3990(5) 0.1130(3) 0.0272(10) Uani 1 1 d . . .
H8A H 0.4250 0.4365 0.0613 0.041 Uiso 1 1 calc R . .
H8B H 0.4325 0.4506 0.1612 0.041 Uiso 1 1 calc R . .
H8C H 0.3203 0.4096 0.1111 0.041 Uiso 1 1 calc R . .
C10 C 1.1157(4) -0.0959(5) 0.2226(2) 0.0177(8) Uani 1 1 d . . .
H10A H 1.0908 -0.1263 0.2763 0.026 Uiso 1 1 calc R . .
H10B H 1.0958 0.0027 0.2125 0.026 Uiso 1 1 calc R . .
H10C H 1.1944 -0.1056 0.2243 0.026 Uiso 1 1 calc R . .
C9 C 0.3850(3) 0.1876(5) 0.1995(2) 0.0172(8) Uani 1 1 d . . .
H9A H 0.3079 0.2091 0.1996 0.026 Uiso 1 1 calc R . .
H9B H 0.4239 0.2302 0.2488 0.026 Uiso 1 1 calc R . .
H9C H 0.3954 0.0855 0.2011 0.026 Uiso 1 1 calc R . .
C3 C 0.7713(3) -0.0457(4) 0.1549(2) 0.0133(7) Uani 1 1 d . . .
H3A H 0.7305 -0.1280 0.1313 0.016 Uiso 1 1 calc R . .
H3B H 0.7735 -0.0518 0.2167 0.016 Uiso 1 1 calc R . .
C12 C 1.0969(3) -0.1314(4) 0.0710(2) 0.0142(7) Uani 1 1 d . . .
H12A H 1.1752 -0.1412 0.0692 0.021 Uiso 1 1 calc R . .
H12B H 1.0769 -0.0321 0.0647 0.021 Uiso 1 1 calc R . .
H12C H 1.0600 -0.1860 0.0253 0.021 Uiso 1 1 calc R . .
N3 N 0.2979(4) 1.0679(5) 0.3587(2) 0.0296(9) Uani 1 1 d . . .
C13 C 0.2504(3) 1.0120(5) 0.4080(2) 0.0180(8) Uani 1 1 d . . .
C14 C 0.1912(4) 0.9398(5) 0.4698(2) 0.0194(8) Uani 1 1 d . . .
H14A H 0.2406 0.8797 0.5045 0.029 Uiso 1 1 calc R . .
H14B H 0.1343 0.8819 0.4411 0.029 Uiso 1 1 calc R . .
H14C H 0.1585 1.0092 0.5053 0.029 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 C1 1.504(5) . ?
N1 C7 1.508(5) . ?
N1 C8 1.499(5) . ?
N1 C9 1.507(5) . ?
N2 C5 1.525(5) . ?
N2 C11 1.485(5) . ?
N2 C10 1.495(5) . ?
N2 C12 1.501(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.526(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C2 1.513(6) . ?
C6 C3 1.516(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.518(6) . ?
C4 C3 1.539(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N3 C13 1.151(6) . ?
C13 C14 1.451(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C7 111.1(3) . . ?
C1 N1 C9 112.2(3) . . ?
C8 N1 C1 106.9(3) . . ?
C8 N1 C7 108.6(3) . . ?
C8 N1 C9 109.4(3) . . ?
C9 N1 C7 108.6(3) . . ?
C11 N2 C5 107.0(3) . . ?
C11 N2 C10 109.4(3) . . ?
C11 N2 C12 108.6(3) . . ?
C10 N2 C5 111.7(3) . . ?
C10 N2 C12 109.1(3) . . ?
C12 N2 C5 111.0(3) . . ?
N1 C1 H1A 108.5 . . ?
N1 C1 H1B 108.5 . . ?
N1 C1 C2 115.3(3) . . ?
H1A C1 H1B 107.5 . . ?
C2 C1 H1A 108.5 . . ?
C2 C1 H1B 108.5 . . ?
H6A C6 H6B 107.7 . . ?
C2 C6 H6A 108.8 . . ?
C2 C6 H6B 108.8 . . ?
C2 C6 C3 113.7(3) . . ?
C3 C6 H6A 108.8 . . ?
C3 C6 H6B 108.8 . . ?
C1 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
C6 C2 C1 109.7(4) . . ?
C6 C2 H2A 109.7 . . ?
C6 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C5 C4 C3 110.6(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
N2 C5 H5A 108.8 . . ?
N2 C5 H5B 108.8 . . ?
C4 C5 N2 113.9(3) . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C3 C4 111.9(3) . . ?
C6 C3 H3A 109.2 . . ?
C6 C3 H3B 109.2 . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C14 179.3(5) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1B Br2 0.99 3.13 4.050(3) 155.7 3_665
C2 H2B Br2 0.99 3.09 3.944(3) 145.5 1_545
C5 H5B Br1 0.99 2.86 3.817(3) 164.1 2_645
C11 H11C Br2 0.98 2.94 3.836(4) 152.2 1_645
C7 H7B Br1 0.98 3.06 3.972(4) 155.0 .
C7 H7C Br2 0.98 2.99 3.915(4) 158.7 1_545
C10 H10A Br1 0.98 3.07 3.978(3) 154.2 2_645
C10 H10B Br1 0.98 3.08 4.002(3) 156.3 1_655
C9 H9A Br1 0.98 3.10 3.996(3) 152.5 .
C9 H9B Br2 0.98 3.02 3.936(3) 155.3 2_645
C12 H12A Br2 0.98 2.84 3.770(3) 158.9 1_645
C12 H12B Br1 0.98 3.03 3.961(3) 158.5 1_655
C12 H12C Br1 0.98 2.83 3.793(3) 167.8 3_655
C14 H14A Br2 0.98 2.93 3.902(4) 172.4 4_576
C14 H14B Br1 0.98 2.93 3.868(4) 160.3 2
C14 H14C Br1 0.98 2.82 3.796(3) 176.0 4_576

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 C6 166.7(3) . . . . ?
C2 C6 C3 C4 175.8(3) . . . . ?
C5 C4 C3 C6 -178.0(3) . . . . ?
C11 N2 C5 C4 -168.9(3) . . . . ?
C7 N1 C1 C2 -71.5(4) . . . . ?
C8 N1 C1 C2 170.2(3) . . . . ?
C10 N2 C5 C4 71.5(4) . . . . ?
C9 N1 C1 C2 50.2(4) . . . . ?
C3 C6 C2 C1 173.8(3) . . . . ?
C3 C4 C5 N2 -163.2(3) . . . . ?
C12 N2 C5 C4 -50.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ljl033_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 952023'
loop_
_audit_author_name
_audit_author_address
'Andrea Daolio'
;polytechnic of Milan
Italy
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H30 N2 2+, C2 H3 N, 2(Cl 1-)'
_chemical_formula_sum            'C14 H33 I2 N3'
_chemical_formula_weight         497.23

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   9.920(2)
_cell_length_b                   12.776(2)
_cell_length_c                   16.440(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.07(2)
_cell_angle_gamma                90.00
_cell_volume                     2071.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    4663
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      28.08
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    3.031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_absorpt_correction_T_min  0.6308
_exptl_absorpt_correction_T_max  0.7149

_exptl_special_details           
; 
Bruker KRYOFLEX low temperature device. 
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            21599
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         30.51
_reflns_number_total             6177
_reflns_number_gt                4303
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    
;
SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., 
Giacovazzo, C., Polidori, G. & Spagna, R. (2003). 
J. Appl. Cryst. 36, 1103.)
;
_computing_structure_refinement  
'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)'

_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565)
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., 
Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). 
J. Appl. Cryst. 39, 453-457
;
_computing_publication_material  SHELXTL


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0247P)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    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6177
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0686
_refine_ls_wR_factor_gt          0.0607
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.973
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.73146(2) 0.079336(18) 0.121651(13) 0.02180(6) Uani 1 1 d . . .
I2 I 0.23891(2) 0.374947(18) 0.111433(13) 0.02335(7) Uani 1 1 d . . .
N1 N 0.7712(3) 0.4226(2) 0.12803(16) 0.0224(7) Uani 1 1 d . . .
N2 N 1.2043(3) 1.0351(2) 0.14034(15) 0.0180(6) Uani 1 1 d . . .
C1 C 0.7829(3) 0.5406(3) 0.1327(2) 0.0239(8) Uani 1 1 d . . .
H1A H 0.7502 0.5640 0.1845 0.029 Uiso 1 1 calc R . .
H1B H 0.7217 0.5710 0.0873 0.029 Uiso 1 1 calc R . .
C2 C 0.9238(4) 0.5845(3) 0.1284(2) 0.0263(8) Uani 1 1 d . . .
H2A H 0.9539 0.5694 0.0741 0.032 Uiso 1 1 calc R . .
H2B H 0.9882 0.5508 0.1705 0.032 Uiso 1 1 calc R . .
C3 C 0.9226(4) 0.7025(3) 0.1426(2) 0.0251(8) Uani 1 1 d . . .
H3A H 0.8538 0.7348 0.1022 0.030 Uiso 1 1 calc R . .
H3B H 0.8956 0.7165 0.1978 0.030 Uiso 1 1 calc R . .
C4 C 1.0586(4) 0.7537(3) 0.1353(2) 0.0267(8) Uani 1 1 d . . .
H4A H 1.0858 0.7392 0.0801 0.032 Uiso 1 1 calc R . .
H4B H 1.1273 0.7216 0.1758 0.032 Uiso 1 1 calc R . .
C5 C 1.0585(4) 0.8713(3) 0.1487(2) 0.0239(8) Uani 1 1 d . . .
H5A H 0.9910 0.9044 0.1080 0.029 Uiso 1 1 calc R . .
H5B H 1.0321 0.8867 0.2039 0.029 Uiso 1 1 calc R . .
C6 C 1.1969(3) 0.9170(3) 0.1409(2) 0.0216(7) Uani 1 1 d . . .
H6A H 1.2287 0.8906 0.0896 0.026 Uiso 1 1 calc R . .
H6B H 1.2605 0.8907 0.1868 0.026 Uiso 1 1 calc R . .
C7 C 1.3518(3) 1.0641(3) 0.1410(2) 0.0290(9) Uani 1 1 d . . .
H7A H 1.3608 1.1405 0.1407 0.044 Uiso 1 1 calc R . .
H7B H 1.3873 1.0349 0.0924 0.044 Uiso 1 1 calc R . .
H7C H 1.4030 1.0357 0.1903 0.044 Uiso 1 1 calc R . .
C8 C 1.1500(4) 1.0831(3) 0.21353(18) 0.0236(8) Uani 1 1 d . . .
H8A H 1.0543 1.0641 0.2138 0.035 Uiso 1 1 calc R . .
H8B H 1.1585 1.1594 0.2110 0.035 Uiso 1 1 calc R . .
H8C H 1.2017 1.0570 0.2635 0.035 Uiso 1 1 calc R . .
C9 C 1.1278(3) 1.0798(3) 0.06456(18) 0.0224(8) Uani 1 1 d . . .
H9A H 1.0317 1.0615 0.0632 0.034 Uiso 1 1 calc R . .
H9B H 1.1642 1.0509 0.0162 0.034 Uiso 1 1 calc R . .
H9C H 1.1377 1.1561 0.0648 0.034 Uiso 1 1 calc R . .
C10 C 0.8523(4) 0.3721(3) 0.2001(2) 0.0296(9) Uani 1 1 d . . .
H10A H 0.8223 0.3994 0.2509 0.044 Uiso 1 1 calc R . .
H10B H 0.9487 0.3878 0.1986 0.044 Uiso 1 1 calc R . .
H10C H 0.8387 0.2961 0.1978 0.044 Uiso 1 1 calc R . .
C11 C 0.6246(4) 0.3965(3) 0.1304(3) 0.0379(10) Uani 1 1 d . . .
H11A H 0.5937 0.4241 0.1808 0.057 Uiso 1 1 calc R . .
H11B H 0.6129 0.3203 0.1288 0.057 Uiso 1 1 calc R . .
H11C H 0.5712 0.4279 0.0830 0.057 Uiso 1 1 calc R . .
C12 C 0.8167(4) 0.3808(3) 0.0508(2) 0.0286(9) Uani 1 1 d . . .
H12A H 0.9124 0.3983 0.0485 0.043 Uiso 1 1 calc R . .
H12B H 0.7621 0.4121 0.0038 0.043 Uiso 1 1 calc R . .
H12C H 0.8054 0.3046 0.0492 0.043 Uiso 1 1 calc R . .
N3 N 0.5411(5) 0.2986(4) 0.8513(3) 0.0799(15) Uani 1 1 d . . .
C13 C 0.4953(4) 0.2522(3) 0.8997(2) 0.0356(10) Uani 1 1 d . . .
C14 C 0.4381(4) 0.1929(3) 0.9622(2) 0.0305(9) Uani 1 1 d . . .
H14A H 0.5113 0.1636 1.0001 0.046 Uiso 1 1 calc R . .
H14B H 0.3824 0.1360 0.9367 0.046 Uiso 1 1 calc R . .
H14C H 0.3817 0.2389 0.9922 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 C12 1.491(4) . ?
N1 C11 1.496(4) . ?
N1 C10 1.506(4) . ?
N1 C1 1.513(4) . ?
N2 C8 1.500(4) . ?
N2 C9 1.501(4) . ?
N2 C7 1.508(4) . ?
N2 C6 1.511(4) . ?
C1 C2 1.515(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.526(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.515(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.519(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.510(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N3 C13 1.125(5) . ?
C13 C14 1.441(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 C11 109.0(3) . . ?
C12 N1 C10 109.4(3) . . ?
C11 N1 C10 108.9(3) . . ?
C12 N1 C1 111.8(3) . . ?
C11 N1 C1 106.9(3) . . ?
C10 N1 C1 110.8(3) . . ?
C8 N2 C9 108.5(3) . . ?
C8 N2 C7 108.9(3) . . ?
C9 N2 C7 108.5(3) . . ?
C8 N2 C6 112.4(2) . . ?
C9 N2 C6 111.3(2) . . ?
C7 N2 C6 107.0(3) . . ?
N1 C1 C2 115.7(3) . . ?
N1 C1 H1A 108.4 . . ?
C2 C1 H1A 108.4 . . ?
N1 C1 H1B 108.4 . . ?
C2 C1 H1B 108.4 . . ?
H1A C1 H1B 107.4 . . ?
C1 C2 C3 109.7(3) . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C4 C3 C2 113.2(3) . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.8 . . ?
C3 C4 C5 113.6(3) . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 110.8(3) . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C5 C6 N2 115.5(3) . . ?
C5 C6 H6A 108.4 . . ?
N2 C6 H6A 108.4 . . ?
C5 C6 H6B 108.4 . . ?
N2 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C14 179.3(5) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 C1 C2 -59.0(4) . . . . ?
C11 N1 C1 C2 -178.1(3) . . . . ?
C10 N1 C1 C2 63.4(4) . . . . ?
N1 C1 C2 C3 -174.2(3) . . . . ?
C1 C2 C3 C4 -177.2(3) . . . . ?
C2 C3 C4 C5 179.7(3) . . . . ?
C3 C4 C5 C6 179.8(3) . . . . ?
C4 C5 C6 N2 171.1(3) . . . . ?
C8 N2 C6 C5 54.7(4) . . . . ?
C9 N2 C6 C5 -67.4(4) . . . . ?
C7 N2 C6 C5 174.2(3) . . . . ?

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
C1 H1A I1 0.99 3.18 4.086(3) 153.2 2_655
C6 H6B I2 0.99 3.32 4.090(3) 135.7 2_655
C7 H7A I2 0.98 3.25 4.141(4) 152.5 1_665
C8 H8C I2 0.98 3.12 3.987(3) 148.4 2_655
C9 H9A I1 0.98 3.23 4.138(4) 154.4 1_565
C9 H9B I1 0.98 3.08 4.044(3) 169.4 3_765
C9 H9C I2 0.98 3.04 3.981(3) 161.1 1_665
C10 H10A I1 0.98 3.19 4.099(4) 154.5 2_655
C10 H10C I1 0.98 3.18 4.094(4) 156.6 .
C11 H11B I1 0.98 3.30 4.194(4) 152.3 .
C12 H12A I2 0.98 3.31 4.202(4) 152.6 1_655
C12 H12B I2 0.98 3.31 4.104(4) 138.9 3_665
C12 H12C I1 0.98 3.23 4.137(4) 154.9 .
C14 H14A I1 0.98 3.00 3.980(4) 177.6 1_556
C14 H14B I1 0.98 3.09 4.042(4) 164.8 3_656
C14 H14C I2 0.98 3.08 4.045(4) 170.4 1_556

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        28.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.953
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.147
####################################################################### 
# 
# 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_mz174
_database_code_depnum_ccdc_archive 'CCDC 952024'
loop_
_audit_author_name
_audit_author_address
'Andrea Daolio'
;polytechnic of Milan
Italy
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;
_audit_creation_date             2021-10-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H30 N2 2+,  2(Br 1-)'
_chemical_formula_sum            'C12 H30 Br2 N2'
_chemical_formula_weight         362.20
_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 0.0033 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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   5.4796(4)
_cell_length_b                   13.1109(11)
_cell_length_c                   11.5815(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.580(4)
_cell_angle_gamma                90.00
_cell_volume                     830.42(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4493
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      31.74
_cell_measurement_theta_min      2.35
_exptl_absorpt_coefficient_mu    4.864
_exptl_absorpt_correction_T_max  0.2661
_exptl_absorpt_correction_T_min  0.1935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       pseudo-hexagonal
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
Data were collected at low temperature to prevent hydration using a
Bruker KRYOFLEX low temperature device. 
;
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13885
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         32.79
_diffrn_reflns_theta_min         3.11
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2274
_reflns_number_total             2897
_reflns_threshold_expression     I>2σ(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  
'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)'
_computing_structure_solution    
;
SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., 
Giacovazzo, C., Polidori, G. & Spagna, R. (2003). 
J. Appl. Cryst. 36, 1103.)
;
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2897
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0235
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0216P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0441
_refine_ls_wR_factor_ref         0.0481
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1A(0.016) H1B(0.016) H2A(0.019) H2B(0.019) H4A(0.021) H4B(0.021)
 H4C(0.021) H5A(0.023) H5B(0.023) H5C(0.023) H6A(0.025) H6B(0.025) H6C(0.025)
 H3A(0.02) H3B(0.02)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.37712(3) 0.103133(11) 0.185334(12) 0.01466(5) Uani 1 1 d . . .
N1 N 0.9751(2) 0.32260(9) 0.38060(10) 0.0111(2) Uani 1 1 d . . .
C1 C 1.1017(3) 0.22695(11) 0.42667(13) 0.0131(3) Uani 1 1 d . . .
H1A H 1.185(3) 0.2501(13) 0.4999(15) 0.016 Uiso 1 1 d . . .
H1B H 1.218(3) 0.2077(13) 0.3713(14) 0.016 Uiso 1 1 d . . .
C2 C 0.9325(3) 0.13685(11) 0.44240(14) 0.0156(3) Uani 1 1 d . . .
H2A H 0.855(3) 0.1148(13) 0.3693(17) 0.019 Uiso 1 1 d . . .
H2B H 0.801(3) 0.1543(14) 0.4957(15) 0.019 Uiso 1 1 d . . .
C4 C 0.8058(3) 0.36261(12) 0.46618(13) 0.0142(3) Uani 1 1 d . . .
H4A H 0.676(3) 0.3130(14) 0.4805(15) 0.021 Uiso 1 1 d . . .
H4B H 0.735(3) 0.4211(14) 0.4353(17) 0.021 Uiso 1 1 d . . .
H4C H 0.891(3) 0.3712(13) 0.5387(17) 0.021 Uiso 1 1 d . . .
C5 C 1.1672(3) 0.40160(12) 0.36241(14) 0.0150(3) Uani 1 1 d . . .
H5A H 1.255(3) 0.4154(13) 0.4341(17) 0.023 Uiso 1 1 d . . .
H5B H 1.089(3) 0.4627(15) 0.3350(15) 0.023 Uiso 1 1 d . . .
H5C H 1.272(3) 0.3787(13) 0.3077(16) 0.023 Uiso 1 1 d . . .
C6 C 0.8386(3) 0.30348(13) 0.26690(13) 0.0169(3) Uani 1 1 d . . .
H6A H 0.712(4) 0.2587(14) 0.2748(17) 0.025 Uiso 1 1 d . . .
H6B H 0.952(3) 0.2748(15) 0.2165(16) 0.025 Uiso 1 1 d . . .
H6C H 0.781(3) 0.3650(14) 0.2384(17) 0.025 Uiso 1 1 d . . .
C3 C 1.0798(3) 0.04667(11) 0.49189(14) 0.0167(3) Uani 1 1 d . . .
H3A H 1.167(3) 0.0659(13) 0.5640(16) 0.020 Uiso 1 1 d . . .
H3B H 1.210(3) 0.0298(13) 0.4375(15) 0.020 Uiso 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 C1 1.5142(17) . ?
N1 C4 1.4943(18) . ?
N1 C5 1.5009(18) . ?
N1 C6 1.4943(18) . ?
C1 H1A 0.984(17) . ?
C1 H1B 0.965(17) . ?
C1 C2 1.520(2) . ?
C2 H2A 0.967(19) . ?
C2 H2B 1.005(17) . ?
C2 C3 1.523(2) . ?
C4 H4A 0.985(18) . ?
C4 H4B 0.921(19) . ?
C4 H4C 0.94(2) . ?
C5 H5A 0.95(2) . ?
C5 H5B 0.953(19) . ?
C5 H5C 0.933(19) . ?
C6 H6A 0.92(2) . ?
C6 H6B 0.954(19) . ?
C6 H6C 0.919(19) . ?
C3 C3 1.523(3) 3_756 ?
C3 H3A 0.970(18) . ?
C3 H3B 1.003(17) . ?

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 C1 110.30(11) . . ?
C4 N1 C5 108.71(11) . . ?
C4 N1 C6 110.26(12) . . ?
C5 N1 C1 108.12(11) . . ?
C6 N1 C1 111.38(11) . . ?
C6 N1 C5 107.99(11) . . ?
N1 C1 H1A 103.0(10) . . ?
N1 C1 H1B 106.8(10) . . ?
N1 C1 C2 114.60(12) . . ?
H1A C1 H1B 111.5(14) . . ?
C2 C1 H1A 112.8(10) . . ?
C2 C1 H1B 108.0(10) . . ?
C1 C2 H2A 111.4(11) . . ?
C1 C2 H2B 111.3(10) . . ?
C1 C2 C3 109.59(12) . . ?
H2A C2 H2B 108.3(14) . . ?
C3 C2 H2A 106.9(10) . . ?
C3 C2 H2B 109.2(10) . . ?
N1 C4 H4A 111.4(10) . . ?
N1 C4 H4B 107.3(11) . . ?
N1 C4 H4C 109.8(11) . . ?
H4A C4 H4B 108.9(16) . . ?
H4A C4 H4C 104.6(14) . . ?
H4B C4 H4C 114.9(16) . . ?
N1 C5 H5A 109.2(11) . . ?
N1 C5 H5B 108.8(11) . . ?
N1 C5 H5C 110.0(11) . . ?
H5A C5 H5B 108.9(15) . . ?
H5A C5 H5C 110.8(16) . . ?
H5B C5 H5C 109.2(15) . . ?
N1 C6 H6A 111.1(12) . . ?
N1 C6 H6B 107.3(11) . . ?
N1 C6 H6C 108.1(12) . . ?
H6A C6 H6B 109.4(17) . . ?
H6A C6 H6C 110.7(16) . . ?
H6B C6 H6C 110.3(17) . . ?
C2 C3 H3A 110.1(11) . . ?
C2 C3 H3B 108.3(10) . . ?
C3 C3 C2 112.03(16) 3_756 . ?
C3 C3 H3A 111.0(11) 3_756 . ?
C3 C3 H3B 109.6(10) 3_756 . ?
H3A C3 H3B 105.5(14) . . ?

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 C3 -178.52(12) . . . . ?
C1 C2 C3 C3 -179.23(16) . . . 3_756 ?
C4 N1 C1 C2 65.05(15) . . . . ?
C5 N1 C1 C2 -176.21(12) . . . . ?
C6 N1 C1 C2 -57.72(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_jm044
_database_code_depnum_ccdc_archive 'CCDC 2119854'
loop_
_audit_author_name
_audit_author_address
'Andrea Daolio'
;polytechnic of Milan
Italy
;
_audit_update_record             
;
2022-02-09 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;

_audit_creation_date             2020-5-28
_audit_creation_method           'Tonto 19.12.17 github v. dd352d58'

# ============
# QCr software
# ============

_QCr_software                    Tonto
_QCr_software_version            '19.12.17 v. dd352d58'
_QCr_software_platform           Linux-4.15.0-72-generic
_QCr_software_build_date         '2019-12-17 16:54'
_QCr_software_website            https://github.com/dylan-jayatilaka/tonto

# ========
# Chemical
# ========

_chemical_formula_moiety         'C12 H30 N2 2+, 2(Br 1-), 2(H2 O)'
_chemical_formula_sum            'C12 H34 Br2 N2 O2'
_chemical_formula_weight         398.23

# ==========
# QCr method
# ==========

_QCr_calc_method                 'Kohn-Sham/b3lypgxb3lypgc/SCCF L=1 R=8.0 A'
_QCr_calc_spinorbital_kind       restricted
_QCr_calc_gaussian_basis_set     DGDZVP
_QCr_calc_gaussian_basis_set_kind cartesian
_QCr_calc_basis_max_l            2

_QCr_calc_unit                   'See _atom_site_* in tonto.cif2'
_QCr_calc_unit_spin_multiplicity 1
_QCr_calc_unit_n_electrons       206
_QCr_calc_unit_n_alpha_electrons 103
_QCr_calc_unit_n_beta_electrons  103

_QCr_Becke_grid_kind             mura_knowles
_QCr_Becke_grid_accuracy         high
_QCr_Becke_grid_L_angular_grid   35
_QCr_Becke_grid_L_H_angular_grid 29
_QCr_Becke_grid_reduce_L_H_ang_grid T
_QCr_Becke_grid_core_pruning_scheme treutler_ahlrichs
_QCr_Becke_grid_scale_H-He_grid  T
_QCr_Becke_grid_n_pts_for_row_1  5890
_QCr_Becke_grid_n_pts_for_row_2  9212
_QCr_Becke_grid_n_pts_for_row_3  10542
_QCr_Becke_grid_n_radial_H_pts   35
_QCr_Becke_grid_H_pts_per_n_shell 5
_QCr_Becke_grid_basis_fn_cutoff  .1E-09
_QCr_Becke_grid_rho_cutoff       .1E-05

# =======
# Crystal
# =======

_exptl_crystal_description       table
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412

# ==============
# Absortion data
# ==============

_exptl_absorpt_coefficient_mu    4.501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_absorpt_correction_T_min  0.2766
_exptl_absorpt_correction_T_max  0.4005

# ========
# Symmetry
# ========

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'p 1 21/c 1'
_symmetry_space_group_name_Hall  '-p 2ybc'
_symmetry_Int_Tables_number      14

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

# =========
# Unit cell
# =========

_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    9842
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      30.02

_cell_length_a                   7.3339(13)
_cell_length_b                   18.292(3)
_cell_length_c                   7.0915(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.824(4)
_cell_angle_gamma                90.00
_cell_volume                     900.4(3)

_cell_formula_units_Z            2.000000

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   HAR

# ===============
# Refinement data
# ===============

_refine_ls_kind                  'Hirshfeld atom refinement (HAR)'
_refine_ls_method_description    
;
   S.C. Capelli, H.-B. Burgi, B. Dittrich, S.Grabowsky
   and Dylan Jayatilaka, IUCrJ (2014). 1, 361-379
;
_refine_QCr_Psi_constraint       none

_refine_ls_SVD_threshold         0.1E-02
_refine_ls_coordinate_system     cartesian
_refine_ls_structure_factor_coeff F
_refine_ls_matrix_type           full
_refine_ls_R_factor_gt           0.0181
_refine_ls_R_factor_all          0.0181
_refine_ls_wR_factor_gt          0.0201
_refine_ls_wR_factor_all         0.0201
_refine_ls_R_Fsqd_factor         0.0233
_refine_ls_goodness_of_fit_gt    3.0720
_refine_ls_goodness_of_fit_all   3.0720
_refine_ls_number_reflns         2450
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_number_constraints    93
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_shift/su_conv_tol     0.0100
_refine_ls_shift/su_max          0.0014
_refine_ls_shift/su_max_mean     0.0003
_refine_ls_shift/su_max_par      'H3A px'
_refine_ls_extinction_method     none

_refine_diff_density_max         0.3988
_refine_diff_density_min         -0.4453
_refine_diff_density_rms         0.0475

_refine_special_details          
;
  .  Hirshfeld atom refinement:
     .  Uses aspherical atomic scattering factors
        obtained from Hirshfeld partitioning of a
        gaussian quantum chemical wavefunction.
     .  Hirshfeld weight functions obtained from
        spherically averaged restricted atomic
        densities.
  .  Wavefunction type : B3LYP using cluster charges,
                        radius=8.0 angstrom
  .  Gaussian basis set: DGDZVP
  .  Refinement based on |F| with weight=1/sigma(|F|)
  .  Negative |F|^^2 were pruned from the data
  .  |F| < 3.0 sigma(|F|) were pruned from the data
  .  Eigenvalues < 0.1E-04 removed from normal equations
  . If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
;

# ==========
# Atom types
# ==========
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction (B3LYP).'
H H 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction (B3LYP).'
N N 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction (B3LYP).'
O O 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction (B3LYP).'
Br Br 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction (B3LYP).'

# ======================
# Fractional coordinates
# ======================

loop_
_atom_site_label
_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_disorder_group
Br1 0.308810(16) 0.367179(6) 0.167385(18) 0.01479(8) Uani 1.000000 0
N1 0.64181(15) 0.12559(5) 0.28355(17) 0.0127(5) Uani 1.000000 0
C1 0.76377(19) 0.11945(7) 0.1481(2) 0.0137(6) Uani 1.000000 0
H1A 0.8522(19) 0.1696(8) 0.171(2) 0.025(4) Uiso 1.000000 0
H1B 0.661(2) 0.1240(7) -0.002(3) 0.031(4) Uiso 1.000000 0
C2 0.88433(18) 0.04994(7) 0.17605(19) 0.0140(6) Uani 1.000000 0
H2A 0.8091(18) 0.0006(8) 0.199(2) 0.038(5) Uiso 1.000000 0
H2B 1.015(2) 0.0527(7) 0.314(2) 0.034(4) Uiso 1.000000 0
C3 0.94296(18) 0.03532(6) -0.00846(19) 0.0138(6) Uani 1.000000 0
H3A 0.8191(19) 0.0295(7) -0.129(2) 0.031(4) Uiso 1.000000 0
H3B 1.0294(18) 0.0786(7) -0.034(2) 0.025(4) Uiso 1.000000 0
C4 0.5520(2) 0.20000(7) 0.2550(2) 0.0205(7) Uani 1.000000 0
H4A 0.470(2) 0.2068(8) 0.101(2) 0.037(4) Uiso 1.000000 0
H4B 0.6638(18) 0.2406(8) 0.304(2) 0.025(4) Uiso 1.000000 0
H4C 0.471(2) 0.2068(8) 0.348(3) 0.044(5) Uiso 1.000000 0
C5 0.7616(2) 0.11658(8) 0.4973(2) 0.0211(7) Uani 1.000000 0
H5A 0.668(2) 0.1266(7) 0.585(3) 0.042(5) Uiso 1.000000 0
H5B 0.874(3) 0.1561(10) 0.534(3) 0.060(5) Uiso 1.000000 0
H5C 0.824(2) 0.0605(10) 0.527(3) 0.055(5) Uiso 1.000000 0
C6 0.48327(19) 0.06996(7) 0.2306(2) 0.0177(7) Uani 1.000000 0
H6A 0.384(2) 0.0814(8) 0.328(2) 0.038(4) Uiso 1.000000 0
H6B 0.543(2) 0.0183(8) 0.258(2) 0.041(4) Uiso 1.000000 0
H6C 0.390(2) 0.0784(8) 0.072(2) 0.040(5) Uiso 1.000000 0
O1 1.03623(14) 0.27236(6) 0.40048(17) 0.0414(7) Uani 1.000000 0
H1 1.131000(0) 0.236100(0) 0.485000(0) 0.066000(0) Uiso 1.000000 0
H2 1.132000(0) 0.297000(0) 0.323000(0) 0.127000(0) Uiso 1.000000 0


# ====
# ADPs
# ====



# ===========
# Reflections
# ===========

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            30772
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0146
_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         30.24

_shelx_F_calc_maximum            158.221708

_reflns_d_resolution_high        6.941640
_reflns_d_resolution_low         0.705566
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                2450
_reflns_number_total             2450
_reflns_threshold_expression     'F>0 & F/u(F)>3.0 & |F_calc|>10^-3'


# ============
# Bond lengths
# ============

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C1 . 1.5131(16) yes
N1 . C4 . 1.4971(15) yes
N1 . C5 . 1.4955(16) yes
N1 . C6 . 1.4990(15) yes
C1 . C2 . 1.5247(17) yes
C2 . C3 . 1.5270(18) yes
C1 . H1A . 1.105(14) yes
C1 . H1B . 1.091(16) yes
C2 . H2A . 1.097(15) yes
C2 . H2B . 1.129(14) yes
C3 . H3A . 1.031(13) yes
C3 . H3B . 1.065(13) yes
C4 . H4A . 1.072(15) yes
C4 . H4B . 1.077(14) yes
C4 . H4C . 1.025(17) yes
C5 . H5A . 1.08(2) yes
C5 . H5B . 1.065(18) yes
C5 . H5C . 1.117(17) yes
C6 . H6A . 1.171(16) yes
C6 . H6B . 1.032(14) yes
C6 . H6C . 1.123(16) yes

# ===========
# Bond Angles
# ===========

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 . C1 . C2 . 114.60(10) yes
N1 . C1 . H1A . 106.5(7) yes
N1 . C1 . H1B . 104.4(9) yes
N1 . C4 . H4A . 108.6(8) yes
N1 . C4 . H4B . 109.1(7) yes
N1 . C4 . H4C . 110.1(9) yes
N1 . C5 . H5A . 107.1(9) yes
N1 . C5 . H5B . 109.0(10) yes
N1 . C5 . H5C . 111.3(9) yes
N1 . C6 . H6A . 108.0(7) yes
N1 . C6 . H6B . 109.2(8) yes
N1 . C6 . H6C . 109.1(8) yes
C1 . N1 . C4 . 107.82(10) yes
C1 . N1 . C5 . 111.17(11) yes
C1 . N1 . C6 . 111.10(10) yes
C4 . N1 . C5 . 109.04(10) yes
C4 . N1 . C6 . 108.15(10) yes
C5 . N1 . C6 . 109.48(10) yes
C1 . C2 . C3 . 110.28(10) yes
C1 . C2 . H2A . 114.0(7) yes
C1 . C2 . H2B . 111.7(7) yes
C2 . C1 . H1A . 112.7(7) yes
C2 . C1 . H1B . 112.3(7) yes
C2 . C3 . H3A . 108.0(8) yes
C2 . C3 . H3B . 111.3(8) yes
C3 . C2 . H2A . 106.1(8) yes
C3 . C2 . H2B . 110.7(8) yes
H1A . C1 . H1B . 105.5(9) yes
H2A . C2 . H2B . 103.8(10) yes
H3A . C3 . H3B . 110.5(10) yes
H4A . C4 . H4B . 111.6(10) yes
H4A . C4 . H4C . 113.1(12) yes
H4B . C4 . H4C . 104.1(11) yes
H5A . C5 . H5B . 109.3(13) yes
H5A . C5 . H5C . 110.4(12) yes
H5B . C5 . H5C . 109.8(13) yes
H6A . C6 . H6B . 110.8(12) yes
H6A . C6 . H6C . 106.1(11) yes
H6B . C6 . H6C . 113.4(12) yes

# ================
# Instruction file
# ================
####################################################################### 
# 
# 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_mz174_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2119853'
loop_
_audit_author_name
_audit_author_address
'Andrea Daolio'
;polytechnic of Milan
Italy
;
_audit_update_record             
;
2022-08-18 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;
_audit_creation_date             2022-08-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
# ========
# Chemical
# ========
_chemical_formula_moiety         'C12 H30 N2 2+,  2(Br 1-)'
_chemical_formula_sum            'C12 H30 Br2 N2'
_chemical_formula_weight         362.2043
# ==========
# Atom types
# ==========
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction (B3LYP).'
H H 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction (B3LYP).'
N N 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction (B3LYP).'
Br Br 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction (B3LYP).'

# ========
# Symmetry
# ========
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-p 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 '+x, +y, +z'
2 '-x, -y, -z'
3 '-x, +y+1/2, -z+1/2'
4 '+x, -y+1/2, +z+1/2'

_symmetry_Int_Tables_number      14
_cell_length_a                   5.4796(4)
_cell_length_b                   13.1109(11)
_cell_length_c                   11.5815(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.580(4)
_cell_angle_gamma                90.00
_cell_volume                     830.42(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4493
# =========
# Unit cell
# =========
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      31.74
_cell_measurement_theta_min      2.35
# ==============
# Absortion data
# ==============
_exptl_absorpt_coefficient_mu    4.864
_exptl_absorpt_correction_T_max  0.2661
_exptl_absorpt_correction_T_min  0.1935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# =======
# Crystal
# =======
_exptl_crystal_description       pseudo-hexagonal
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13885
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         32.79
_diffrn_reflns_theta_min         3.11
# ===========
# Reflections
# ===========
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_d_resolution_high        6.555450
_reflns_d_resolution_low         0.657840
_reflns_limit_h_max              7
_reflns_limit_h_min              -8
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                2351
_reflns_number_total             2351
_reflns_threshold_expression     'F>0 & F/u(F)>3.0 & |F_calc|>10^-3'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_diff_density_max         0.5089
_refine_diff_density_min         -0.3598
_refine_diff_density_rms         0.0756
_refine_ls_coordinate_system     cartesian
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.2126
_refine_ls_goodness_of_fit_gt    1.2126
_refine_ls_hydrogen_treatment    refall
# ===============
# Refinement data
# ===============
_refine_ls_kind                  'Hirshfeld atom refinement (HAR)'
_refine_ls_matrix_type           full
_refine_ls_method_description    
;
   S.C. Capelli, H.-B. Burgi, B. Dittrich, S.Grabowsky
   and Dylan Jayatilaka, IUCrJ (2014). 1, 361-379
;
_refine_ls_number_constraints    75
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2351
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0243
_refine_ls_R_Fsqd_factor         0.0279
_refine_ls_shift/su_conv_tol     0.0100
_refine_ls_shift/su_max          0.0011
_refine_ls_shift/su_max_mean     0.0003
_refine_ls_shift/su_max_par      'H3A Uxz'
_refine_ls_structure_factor_coeff F
_refine_ls_SVD_threshold         0.1E-02
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.0161
_refine_ls_wR_factor_gt          0.0161
_refine_QCr_Psi_constraint       none
_refine_special_details          
;
  .  Hirshfeld atom refinement:
     .  Uses aspherical atomic scattering factors
        obtained from Hirshfeld partitioning of a
        gaussian quantum chemical wavefunction.
     .  Hirshfeld weight functions obtained from
        spherically averaged restricted atomic
        densities.
  .  Wavefunction type : B3LYP using cluster charges,
                        radius=8.0 angstrom
  .  Gaussian basis set: DGDZVP
  .  Refinement based on |F| with weight=1/sigma(|F|)
  .  Negative |F|^^2 were pruned from the data
  .  |F| < 3.0 sigma(|F|) were pruned from the data
  .  Eigenvalues < 0.1E-04 removed from normal equations
  . If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   HAR
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
# ======================
# Fractional coordinates
# ======================
loop_
_atom_site_label
_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_disorder_group
N1 0.97522(18) 0.32251(8) 0.38059(9) 0.0117(5) Uani 1.000000 .
C1 1.1012(3) 0.22699(10) 0.42630(12) 0.0137(7) Uani 1.000000 .
H1A 1.189(3) 0.2484(12) 0.5043(14) 0.031(5) Uiso 1.000000 .
H1B 1.235(3) 0.2068(12) 0.3646(14) 0.032(5) Uiso 1.000000 .
C2 0.9330(3) 0.13706(10) 0.44229(13) 0.0163(7) Uani 1.000000 .
H2A 0.851(3) 0.1146(13) 0.3614(15) 0.040(5) Uiso 1.000000 .
H2B 0.792(3) 0.1556(13) 0.4992(14) 0.037(5) Uiso 1.000000 .
C4 0.8057(3) 0.36236(11) 0.46622(13) 0.0155(7) Uani 1.000000 .
H4A 0.666(3) 0.3054(12) 0.4772(13) 0.027(4) Uiso 1.000000 .
H4B 0.732(3) 0.4286(13) 0.4343(15) 0.038(5) Uiso 1.000000 .
H4C 0.912(3) 0.3723(11) 0.5447(14) 0.031(5) Uiso 1.000000 .
C5 1.1665(2) 0.40142(11) 0.36259(12) 0.0160(6) Uani 1.000000 .
H5A 1.264(3) 0.4125(12) 0.4423(15) 0.037(5) Uiso 1.000000 .
H5B 1.076(3) 0.4681(13) 0.3321(14) 0.037(5) Uiso 1.000000 .
H5C 1.282(3) 0.3731(13) 0.3008(15) 0.044(5) Uiso 1.000000 .
C6 0.8392(3) 0.30334(12) 0.26709(12) 0.0179(7) Uani 1.000000 .
H6A 0.699(3) 0.2502(13) 0.2776(15) 0.037(5) Uiso 1.000000 .
H6B 0.970(3) 0.2709(13) 0.2112(14) 0.035(5) Uiso 1.000000 .
H6C 0.775(3) 0.3723(12) 0.2388(14) 0.035(5) Uiso 1.000000 .
C3 1.0797(3) 0.04671(10) 0.49183(13) 0.0176(7) Uani 1.000000 .
H3A 1.169(3) 0.0658(13) 0.5740(16) 0.049(5) Uiso 1.000000 .
H3B 1.219(3) 0.0288(12) 0.4327(14) 0.035(5) Uiso 1.000000 .
Br5 1.62293(2) 0.603142(10) 0.314667(12) 0.01452(6) Uani 1.000000 .

# ====
# ADPs
# ====

# ============
# Bond lengths
# ============
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C1 . 1.5098(16) yes
N1 . C4 . 1.4948(16) yes
N1 . C5 . 1.4966(17) yes
N1 . C6 . 1.4914(16) yes
C1 . H1A . 1.034(16) yes
C1 . H1B . 1.086(16) yes
C1 . C2 . 1.5150(18) yes
C2 . H2A . 1.055(17) yes
C2 . H2B . 1.075(16) yes
C2 . C3 . 1.5234(19) yes
C4 . H4A . 1.083(15) yes
C4 . H4B . 1.018(17) yes
C4 . H4C . 1.057(16) yes
C5 . H5A . 1.047(17) yes
C5 . H5B . 1.054(17) yes
C5 . H5C . 1.052(17) yes
C6 . H6A . 1.051(17) yes
C6 . H6B . 1.083(17) yes
C6 . H6C . 1.016(16) yes
C3 . H3A . 1.071(18) yes
C3 . H3B . 1.084(16) yes

# ===========
# Bond Angles
# ===========
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 . N1 . C4 . 110.29(10) yes
C1 . N1 . C5 . 108.26(10) yes
C1 . N1 . C6 . 111.20(10) yes
C4 . N1 . C5 . 108.69(10) yes
C4 . N1 . C6 . 110.27(10) yes
C5 . N1 . C6 . 108.04(10) yes
N1 . C1 . H1A . 104.9(9) yes
N1 . C1 . H1B . 106.4(9) yes
N1 . C1 . C2 . 114.85(11) yes
H1A . C1 . H1B . 110.3(12) yes
C2 . C1 . H1A . 110.9(9) yes
C2 . C1 . H1B . 109.3(9) yes
C1 . C2 . H2A . 109.6(9) yes
C1 . C2 . H2B . 111.4(9) yes
C1 . C2 . C3 . 109.91(11) yes
H2A . C2 . H2B . 109.1(12) yes
C3 . C2 . H2A . 107.6(9) yes
C3 . C2 . H2B . 109.1(9) yes
N1 . C4 . H4A . 108.1(8) yes
N1 . C4 . H4B . 107.8(9) yes
N1 . C4 . H4C . 106.3(9) yes
H4A . C4 . H4B . 111.3(12) yes
H4A . C4 . H4C . 109.9(11) yes
H4B . C4 . H4C . 113.1(12) yes
N1 . C5 . H5A . 107.2(9) yes
N1 . C5 . H5B . 107.6(9) yes
N1 . C5 . H5C . 107.9(9) yes
H5A . C5 . H5B . 112.4(13) yes
H5A . C5 . H5C . 110.7(13) yes
H5B . C5 . H5C . 110.7(12) yes
N1 . C6 . H6A . 109.8(9) yes
N1 . C6 . H6B . 106.3(9) yes
N1 . C6 . H6C . 106.1(9) yes
H6A . C6 . H6B . 109.0(13) yes
H6A . C6 . H6C . 112.8(12) yes
H6B . C6 . H6C . 112.6(13) yes
C2 . C3 . H3A . 110.6(9) yes
C2 . C3 . H3B . 107.9(9) yes
H3A . C3 . H3B . 108.3(13) yes

_shelx_F_calc_maximum            150.386532
# ================
# Instruction file
# ================
_olex2_submission_special_instructions 'No special instructions were received'
_QCr_Becke_grid_accuracy         high
_QCr_Becke_grid_basis_fn_cutoff  .1E-09
_QCr_Becke_grid_core_pruning_scheme treutler_ahlrichs
_QCr_Becke_grid_H_pts_per_n_shell 5
_QCr_Becke_grid_kind             mura_knowles
_QCr_Becke_grid_L_angular_grid   35
_QCr_Becke_grid_L_H_angular_grid 29
_QCr_Becke_grid_n_pts_for_row_1  5890
_QCr_Becke_grid_n_pts_for_row_2  9212
_QCr_Becke_grid_n_pts_for_row_3  10542
_QCr_Becke_grid_n_radial_H_pts   35
_QCr_Becke_grid_reduce_L_H_ang_grid T
_QCr_Becke_grid_rho_cutoff       .1E-05
_QCr_Becke_grid_scale_H-He_grid  T
_QCr_calc_basis_max_l            2
_QCr_calc_gaussian_basis_set     DGDZVP
_QCr_calc_gaussian_basis_set_kind cartesian
# ==========
# QCr method
# ==========
_QCr_calc_method                 'Kohn-Sham/b3lypgxb3lypgc/SCCF L=1 R=8.0 A'
_QCr_calc_spinorbital_kind       restricted
_QCr_calc_unit                   'See _atom_site_* in tonto.cif2'
_QCr_calc_unit_n_alpha_electrons 93
_QCr_calc_unit_n_beta_electrons  93
_QCr_calc_unit_n_electrons       186
_QCr_calc_unit_spin_multiplicity 1
# ============
# QCr software
# ============
_QCr_software                    Tonto
_QCr_software_build_date         '2019-12-17 16:54'
_QCr_software_platform           Linux-4.15.0-72-generic
_QCr_software_version            '19.12.17 v. dd352d58'
_QCr_software_website            https://github.com/dylan-jayatilaka/tonto
