A new class of unique quinoidal-like imidazoliumyl tetrazinides: synthesis, structure, and mechanism
Geng, Yanxue; Sun, Weijun; Zhang, Weixu; Li, Mengyao; Wang, Guo; Wang, Jianchun; New Journal of Chemistry 48 (2024) 3467–3471; doi:10.1039/D3NJ04766K

data_7062978
_publ_section_title
;
 A new class of unique quinoidal-like imidazoliumyl tetrazinides:
 synthesis, structure, and mechanism
;
_journal_issue                   8
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3467
_journal_page_last               3471
_journal_paper_doi               10.1039/D3NJ04766K
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         '0.5(C12 H12 N12 O2), 0.5(H4 O2)'
_chemical_formula_sum            'C6 H9 N6 O2'
_chemical_formula_weight         197.19
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2023-09-18 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1035(3)
_cell_length_b                   6.3113(2)
_cell_length_c                   9.5102(2)
_cell_measurement_reflns_used    1522
_cell_measurement_temperature    298.68(10)
_cell_measurement_theta_max      72.2100
_cell_measurement_theta_min      7.8320
_cell_volume                     846.52(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.68(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -17.00  89.00   0.50    3.00    --    0.00  37.00-150.00  212
  2  \w    -22.00  89.00   0.50    3.00    --    0.00  57.00   0.00  222
  3  \w     71.00 113.00   0.50   10.00    --   94.60 -61.00 150.00   84
  4  \w     93.00 180.00   0.50   10.00    --   94.60  45.00-150.00  174
  5  \w     66.00 146.00   0.50   10.00    --   94.60  77.00 -90.00  160
  6  \w      7.00  73.00   0.50   10.00    --   94.60 -45.00-180.00  132
  7  \w    119.00 155.00   0.50   10.00    --   94.60  45.00 150.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0250408000
_diffrn_orient_matrix_UB_12      -0.1812086000
_diffrn_orient_matrix_UB_13      0.1020364000
_diffrn_orient_matrix_UB_21      -0.0348425000
_diffrn_orient_matrix_UB_22      -0.1350122000
_diffrn_orient_matrix_UB_23      -0.1245119000
_diffrn_orient_matrix_UB_31      0.1004691000
_diffrn_orient_matrix_UB_32      -0.0922814000
_diffrn_orient_matrix_UB_33      -0.0178721000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1243
_diffrn_reflns_av_unetI/netI     0.0799
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2220
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        66.568
_diffrn_reflns_theta_max         66.567
_diffrn_reflns_theta_min         5.611
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.035
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.547
_exptl_crystal_description       needle
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.560
_refine_diff_density_min         -1.358
_refine_diff_density_rms         0.410
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     89
_refine_ls_number_reflns         817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.1227
_refine_ls_R_factor_gt           0.1170
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2392
_refine_ls_wR_factor_ref         0.2478
_reflns_Friedel_coverage         0.000
_reflns_number_gt                694
_reflns_number_total             817
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj04766k2.cif
_cod_data_source_block           20190422-1
_cod_depositor_comments
'Adding full bibliography for 7062975--7062979.cif.'
_cod_database_code               7062978
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C1 N1 H1 Cl1 '
_reflns_odcompleteness_completeness 97.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Fixed Sof: H1A(0.5) H1C(0.5) H1B(0.5) H2A(0.5) H2B(0.5)
3.a Free rotating group:
 O2(H2A,H2B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1C,H1B)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.435
_oxdiff_exptl_absorpt_empirical_full_min 0.127