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_7062975
_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         'C14 H14 N6 O'
_chemical_formula_sum            'C14 H14 N6 O'
_chemical_formula_weight         282.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-09-18 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.3620(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.18010(10)
_cell_length_b                   17.2524(2)
_cell_length_c                   9.19780(10)
_cell_measurement_reflns_used    6423
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1880
_cell_measurement_theta_min      5.1390
_cell_volume                     1272.61(3)
_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      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.984
_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    -13.00  89.00   0.50    0.50    --    0.00  37.00-150.00  204
  2  \w    -89.00   9.00   0.50    0.50    --    0.00 -19.00-120.00  196
  3  \w    -29.00  89.00   0.50    0.50    --    0.00  82.00-180.00  236
  4  \w    -89.00  27.00   0.50    0.50    --    0.00 -77.00   0.00  232
  5  \w    -89.00  13.00   0.50    0.50    --    0.00 -37.00  60.00  204
  6  \w     62.00 123.00   0.50    1.00    --   94.00 -82.00-120.00  122
  7  \w      5.00 104.00   0.50    1.00    --   94.00 -30.00 -30.00  198
  8  \w      6.00 101.00   0.50    1.00    --   94.00 -61.00-150.00  190
  9  \w     76.00 168.00   0.50    1.00    --   94.00  55.00 -38.86  184
 10  \w     46.00 115.00   0.50    1.00    --   94.00 -82.00   0.00  138
 11  \w     12.00 122.00   0.50    1.00    --   94.00 -82.00 120.00  220
 12  \w      5.00  38.00   0.50    1.00    --   94.00 -77.00  90.00   66
 13  \w     61.00  87.00   0.50    1.00    --   94.00 -61.00 120.00   52
 14  \w      5.00 100.00   0.50    1.00    --   94.00 -82.00-150.00  190
 15  \w    121.00 182.00   0.50    1.00    --   94.00  30.00  60.00  122
 16  \w      5.00  50.00   0.50    1.00    --   94.00 -61.00 120.00   90
 17  \w     83.00 115.00   0.50    1.00    --   94.00 -61.00-120.00   64
 18  \w      6.00  97.00   0.50    1.00    --   94.00 -61.00   0.00  182
 19  \w     97.00 123.00   0.50    1.00    --   94.00 -82.00  30.00   52
 20  \w     79.00 180.00   0.50    1.00    --   94.00  45.00 -60.00  202
;
_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      -0.0494204000
_diffrn_orient_matrix_UB_12      -0.0832998000
_diffrn_orient_matrix_UB_13      -0.0509861000
_diffrn_orient_matrix_UB_21      -0.0455446000
_diffrn_orient_matrix_UB_22      0.0280781000
_diffrn_orient_matrix_UB_23      -0.1619158000
_diffrn_orient_matrix_UB_31      0.1799428000
_diffrn_orient_matrix_UB_32      -0.0157612000
_diffrn_orient_matrix_UB_33      -0.0190950000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0815
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6457
_diffrn_reflns_point_group_measured_fraction_full 0.706
_diffrn_reflns_point_group_measured_fraction_max 0.728
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.572
_diffrn_reflns_theta_min         5.536
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.820
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40535
_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 dark violet'
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       rhombohedral
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1623
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0777P)^2^+0.0863P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.474
_reflns_Friedel_fraction_full    0.456
_reflns_Friedel_fraction_max     0.471
_reflns_number_gt                1610
_reflns_number_total             1623
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj04766k2.cif
_cod_data_source_block           swj-1
_cod_depositor_comments
'Adding full bibliography for 7062975--7062979.cif.'
_cod_database_code               7062975
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C14(H14A,H14B), C13(H13A,H13B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C8(H8), C9(H9), C7(H7)
;
_shelx_res_checksum              40578
_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 5.892
_oxdiff_exptl_absorpt_empirical_full_min 0.377