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_7062976
_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         'C15 H10 N6 O, C4 H8 O'
_chemical_formula_sum            'C19 H18 N6 O2'
_chemical_formula_weight         362.39
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-18
_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                 105.501(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0018(9)
_cell_length_b                   10.3586(5)
_cell_length_c                   12.8117(8)
_cell_measurement_reflns_used    4187
_cell_measurement_temperature    294.61(10)
_cell_measurement_theta_max      69.7760
_cell_measurement_theta_min      5.3610
_cell_volume                     1790.61(19)
_computing_cell_refinement       'CrysAlisPro 1.171.39.22a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.22a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.22a (Rigaku OD, 2015)'
_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      294.61(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.998
_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    -89.00  20.00   0.50    1.00    --    0.00 -57.00 -30.00  218
  2  \w     21.00  88.00   0.50    1.00    --    0.00  19.00 -30.00  134
  3  \w     23.00  88.00   0.50    1.00    --    0.00  19.00-120.00  130
  4  \w     20.00  46.00   0.50    1.00    --    0.00  37.00   0.00   52
  5  \w      5.00  50.00   0.50    7.00    --   94.00 -15.00   0.00   90
  6  \w     21.00  46.00   0.50    7.00    --   94.00 -61.00 150.00   50
  7  \w     81.00 183.00   0.50    7.00    --   94.00  45.00 -90.00  204
  8  \w     79.00 174.00   0.50    7.00    --   94.00  61.00 120.00  190
  9  \w     39.00 104.00   0.50    7.00    --   94.00 -30.00   0.00  130
 10  \w     85.00 120.00   0.50    7.00    --   94.00  15.00 -90.00   70
 11  \w     61.00 109.00   0.50    7.00    --   94.00 -61.00 150.00   96
 12  \w      5.00 101.00   0.50    7.00    --   94.00 -45.00   0.00  192
 13  \w    104.00 129.00   0.50    7.00    --   94.00  77.00 -30.00   50
 14  \w     77.00 102.00   0.50    7.00    --   94.00  77.00 -30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: 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      -0.1114107000
_diffrn_orient_matrix_UB_12      0.0270713000
_diffrn_orient_matrix_UB_13      -0.0468164000
_diffrn_orient_matrix_UB_21      0.0246878000
_diffrn_orient_matrix_UB_22      0.1133886000
_diffrn_orient_matrix_UB_23      -0.0660527000
_diffrn_orient_matrix_UB_31      -0.0023710000
_diffrn_orient_matrix_UB_32      -0.0923475000
_diffrn_orient_matrix_UB_33      -0.0950244000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9859
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.559
_diffrn_reflns_theta_min         5.384
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.22a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3158
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.0954
_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^)+(0.1493P)^2^+0.9538P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2801
_refine_ls_wR_factor_ref         0.2988
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2127
_reflns_number_total             3158
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj04766k2.cif
_cod_data_source_block           swj-3
_cod_depositor_comments
'Adding full bibliography for 7062975--7062979.cif.'
_cod_database_code               7062976
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C1 N1 O1 H1'
_reflns_odcompleteness_completeness 99.91
_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. Restrained distances
 O6-C3
 2.1 with sigma of 0.002
 C3-C0AA
 1.4 with sigma of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C1(H1A,H1B), C0AA(H0AA,H0AB), C2(H2A,H2B)
3.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00C(H00C), C00D(H00D), C00F(H00F), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M)
;
_shelx_res_checksum              98942
_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 3.063
_oxdiff_exptl_absorpt_empirical_full_min 0.311