Refreshing the Legacy of Rudolf Nietzki: Benzene-1,2,4,5-tetramine and Related Compounds
Johann O. E. Sosoe; Cédric Malveau; Thierry Maris; Radu Iftimie; James D. Wuest; Journal of Organic Chemistry 88 (2023) 16302–16314; doi:10.1021/acs.joc.3c01793

data_4039021
_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 H12 N4, 2(Cl)'
_chemical_formula_sum            'C6 H12 Cl2 N4'
_chemical_formula_weight         211.10
_chemical_name_systematic
;
4,6-diaminobenzene-1,3-diaminium 
2,5-diaminobenzene-1,4-diaminium dichloride
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_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_date             2022-07-16
_audit_creation_method
;
FinalCif V106 by Daniel Kratzert, Freiburg 2022,
https://dkratzert.de/finalcif.html
;
_cell_angle_alpha                90
_cell_angle_beta                 94.083(3)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   9.4236(6)
_cell_length_b                   14.5883(10)
_cell_length_c                   9.7872(7)
_cell_measurement_reflns_used    6098
_cell_measurement_temperature    150
_cell_measurement_theta_max      57.054
_cell_measurement_theta_min      4.093
_cell_volume                     1342.07(16)
_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    'XT  (Sheldrick, 2015)'
_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 0.993
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       '\w and \f 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  0.0459
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12141
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.027
_diffrn_reflns_theta_min         4.092
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.1993706
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.71
_exptl_absorpt_coefficient_mu    4.075
_exptl_absorpt_correction_T_max  0.5138
_exptl_absorpt_correction_T_min  0.3366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1539 before and 0.0744 after correction.
The Ratio of minimum to maximum transmission is 0.6551.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_description       Plate
_exptl_crystal_F_000             660
_exptl_crystal_recrystallization_method H2O/NaOH
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0458
_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/[\s^2^(Fo^2^)+(0.0872P)^2^+0.2570P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1429
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2128
_reflns_number_total             2656
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            BTA_2HCl.cif
_cod_data_source_block           jw24751
_cod_database_code               4039021
_cod_database_fobs_code 4039021