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_4039023
_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_absolute_configuration unk
_chemical_formula_moiety         'C6 H8 N4'
_chemical_formula_sum            'C6 H8 N4'
_chemical_formula_weight         136.16
_chemical_name_systematic
;
3,6-Diiminocyclohexa-1,4-diene-1,4-diamine
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_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             2022-01-27
_audit_creation_method
;
FinalCif V97 by Daniel Kratzert, Freiburg 2022,
https://dkratzert.de/finalcif.html
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7151(10)
_cell_length_b                   7.7840(8)
_cell_length_c                   7.2910(8)
_cell_measurement_reflns_used    566
_cell_measurement_temperature    100
_cell_measurement_theta_max      69.272
_cell_measurement_theta_min      7.021
_cell_volume                     608.12(11)
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5565
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.244
_diffrn_reflns_theta_min         7.031
_diffrn_source                   'Microfocus Source'
_diffrn_source_current           0.42
_diffrn_source_power             0.0100296
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_diffrn_source_voltage           23.88
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_T_max  0.3220
_exptl_absorpt_correction_T_min  0.1708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1783 before and 0.0606 after correction.
The Ratio of minimum to maximum transmission is 0.5304.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       Fragment
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.228
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         1093
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.227
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0537
_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/[\s^2^(Fo^2^)+(0.0817P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1543
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.922
_reflns_number_gt                893
_reflns_number_total             1093
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            BTA_H2.cif
_cod_data_source_block           jw2423
_cod_database_code               4039023
_cod_database_fobs_code 4039023