#------------------------------------------------------------------------------
#$Date: 2023-12-05 14:40:41 +0100 (Tue 05 de Dec de 2023) $
#$Revision: 288034 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/90/4039022.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4039022
loop_
_publ_author_name
'Johann O. E. Sosoe'
'Cédric Malveau'
'Thierry Maris'
'Radu Iftimie'
'James D. Wuest'
_publ_contact_author_id_orcid    0000-0001-9731-4046
_publ_section_title
;
 Refreshing the Legacy of Rudolf Nietzki: Benzene-1,2,4,5-tetramine and
 Related Compounds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              16302
_journal_page_last               16314
_journal_paper_doi               10.1021/acs.joc.3c01793
_journal_volume                  88
_journal_year                    2023
_chemical_formula_moiety         'C6 H14 N4, 4(Cl)'
_chemical_formula_sum            'C6 H14 Cl4 N4'
_chemical_formula_weight         284.01
_chemical_name_systematic
;
bensene-1,2,4,5-tetraaminium tetrachloride
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           58
_space_group_name_Hall           '-P 2 2n'
_space_group_name_H-M_alt        'P n n m'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_contact_author_email      thierry.maris@umontreal.ca
_audit_contact_author_name       'Thierry Maris'
_audit_contact_author_phone      '+1 514 340 4711 2579'
_audit_creation_method
;
FinalCif V85 by Daniel Kratzert, Freiburg 2021,
https://github.com/dkratzert/FinalCif
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0533(3)
_cell_length_b                   9.6682(3)
_cell_length_c                   7.3499(3)
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.591
_cell_measurement_theta_min      3.979
_cell_volume                     572.27(4)
_computing_cell_refinement
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            11865
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.560
_diffrn_reflns_theta_min         6.222
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.199914
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.9
_exptl_absorpt_coefficient_mu    6.095
_exptl_absorpt_correction_T_max  0.3107
_exptl_absorpt_correction_T_min  0.2067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1216 before and 0.0585 after correction.
The Ratio of minimum to maximum transmission is 0.6653.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_description       Block
_exptl_crystal_F_000             292
_exptl_crystal_recrystallization_method 'crystallized from HCl/H2O'
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.041(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     51
_refine_ls_number_reflns         672
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.0224
_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)+(0.0267P)²+0.2284P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0562
_refine_ls_wR_factor_ref         0.0562
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                672
_reflns_number_total             672
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            BTA_4HCl.cif
_cod_data_source_block           jw23121
_cod_database_code               4039022
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'
5 '-x, -y, -z'
6 'x, y, -z'
7 'x-1/2, -y-1/2, z-1/2'
8 '-x-1/2, y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.72990(11) 0.60825(9) 0.20514(13) 0.0156(2) Uani 1 1 d . . . . .
C1 C 1.000000 0.500000 0.1880(2) 0.0159(3) Uani 1 2 d S T P . .
C2 C 0.86553(12) 0.55457(10) 0.09424(14) 0.0146(2) Uani 1 1 d . . . . .
Cl1 Cl 0.67606(5) 0.38811(4) 0.500000 0.02263(17) Uani 1 2 d S T P . .
Cl2 Cl 0.39907(4) 0.69616(3) 0.000000 0.01762(16) Uani 1 2 d S T P . .
H1A H 0.641(2) 0.6371(18) 0.144(2) 0.030(4) Uiso 1 1 d . . . . .
H1 H 1.000000 0.500000 0.306(3) 0.020(5) Uiso 1 2 d S . P . .
H1B H 0.7005(19) 0.5461(17) 0.281(3) 0.028(4) Uiso 1 1 d . . . . .
H1C H 0.7620(19) 0.6751(16) 0.265(2) 0.026(4) Uiso 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0172(4) 0.0162(4) 0.0134(4) -0.0005(3) 0.0004(3) 0.0009(3)
C1 0.0194(6) 0.0164(6) 0.0118(6) 0.000 0.000 -0.0003(5)
C2 0.0163(4) 0.0129(4) 0.0147(5) -0.0003(4) 0.0012(4) -0.0005(3)
Cl1 0.0356(3) 0.0159(2) 0.0164(2) 0.000 0.000 0.00106(13)
Cl2 0.0176(2) 0.0197(2) 0.0156(2) 0.000 0.000 0.00181(11)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C2 N1 H1A 115.7(11) . .
C2 N1 H1B 108.9(10) . .
C2 N1 H1C 110.0(11) . .
H1A N1 H1B 109.2(15) . .
H1A N1 H1C 106.0(15) . .
H1B N1 H1C 106.8(16) . .
C2 C1 C2 120.43(13) . 2_765
C2 C1 H1 119.78(7) . .
C2 C1 H1 119.78(7) 2_765 .
C1 C2 N1 116.24(10) . .
C2 C2 N1 123.98(5) 6 .
C2 C2 C1 119.78(7) 6 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.4584(13) .
N1 H1A 0.887(18) .
N1 H1B 0.854(18) .
N1 H1C 0.823(17) .
C1 C2 1.3879(12) .
C1 C2 1.3879(12) 2_765
C1 H1 0.87(2) .
C2 C2 1.385(2) 6
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
_geom_hbond_publ_flag
N1 H1A Cl2 0.887(18) 2.293(18) 3.1771(10) 174.8(15) . yes
N1 H1B Cl1 0.854(18) 2.227(19) 3.0684(10) 168.5(15) . yes
N1 H1C Cl2 0.823(17) 2.398(17) 3.1826(10) 159.5(14) 7_676 yes
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
C2 C1 C2 N1 179.48(9) 2_765 . . .
C2 C1 C2 C2 -0.003(1) 2_765 . . 6

_cod_database_fobs_code 4039022
