Probing the Dynamic Covalent Chemistry Behavior of Nitrogen-Centered Di and Tri-Urazole Radicals.
Breton, Gary W.; Martin, Kenneth L.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01425

data_4038665
_publ_section_title
;
 Probing the Dynamic Covalent Chemistry Behavior of Nitrogen-Centered Di
 and Tri-Urazole Radicals.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01425
_journal_year                    2020
_chemical_formula_moiety         'C30 H32 N12 O14'
_chemical_formula_sum            'C30 H32 N12 O14'
_chemical_formula_weight         784.67
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-05-27
_audit_creation_method
;
Olex2 1.3-dev
(compiled 2020.05.22 svn.r1d9e7f8d for OlexSys, GUI svn.r6121)
;
_cell_angle_alpha                80.1888(17)
_cell_angle_beta                 78.9436(18)
_cell_angle_gamma                82.5255(18)
_cell_formula_units_Z            4
_cell_length_a                   13.5250(3)
_cell_length_b                   14.4928(3)
_cell_length_c                   20.6967(4)
_cell_measurement_reflns_used    22931
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      32.6130
_cell_measurement_theta_min      1.6320
_cell_volume                     3903.38(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3-dev (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.865
_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    -30.00  54.00   0.50   16.00    --  -14.26  19.00 -94.00  168
  2  \w      7.00  77.00   0.50   16.00    --   14.26  19.00 -94.00  140
  3  \w     -1.00  39.00   0.50   16.00    --   14.26  57.00 -30.00   80
  4  \w     39.00  64.00   0.50   16.00    --   14.26 178.00-120.00   50
  5  \w    -57.00  24.00   0.50   16.00    --   14.26 -19.00  97.00  162
  6  \w    -16.00  17.00   0.50   16.00    --  -14.26 -99.00 150.00   66
  7  \w     -8.00  18.00   0.50   16.00    --  -14.26 -99.00  90.00   52
  8  \w    -16.00  10.00   0.50   16.00    --   14.26 -99.00  90.00   52
  9  \w    -68.00   1.00   0.50   16.00    --  -14.26 -38.00 -90.00  138
 10  \w    -26.00  -1.00   0.50   16.00    --  -14.26 -99.00-150.00   50
 11  \w    -26.00   7.00   0.50   16.00    --  -14.26 -99.00 -90.00   66
 12  \w    -84.00   0.00   0.50   16.00    --  -14.26 -57.00  30.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0109875000
_diffrn_orient_matrix_UB_12      0.0492465000
_diffrn_orient_matrix_UB_13      -0.0087925000
_diffrn_orient_matrix_UB_21      0.0511634000
_diffrn_orient_matrix_UB_22      0.0064793000
_diffrn_orient_matrix_UB_23      -0.0002407000
_diffrn_orient_matrix_UB_31      0.0120918000
_diffrn_orient_matrix_UB_32      -0.0050003000
_diffrn_orient_matrix_UB_33      -0.0342033000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_unetI/netI     0.0833
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            81618
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.828
_diffrn_reflns_theta_min         1.627
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.524
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.50a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.335
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1029
_refine_ls_number_reflns         27178
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1156
_refine_ls_R_factor_gt           0.0642
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0788P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1663
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15629
_reflns_number_total             27178
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01425_si_002.cif
_cod_data_source_block           gb2019_rextal
_cod_original_cell_volume        3903.35(14)
_cod_database_code               4038665
_shelx_shelxl_version_number     2018/3
_cell_oxdiff_angle_alpha         80.1888(17)
_cell_oxdiff_angle_beta          78.9436(18)
_cell_oxdiff_angle_gamma         82.5255(18)
_cell_oxdiff_length_a            13.5250(3)
_cell_oxdiff_length_b            14.4928(3)
_cell_oxdiff_length_c            20.6967(4)
_cell_oxdiff_measurement_reflns_used 22931
_cell_oxdiff_volume              3903.35(14)
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.965
_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
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C26(H26), C41(H41), C56(H56)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C5(H5A,H5B,H5C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C),
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C35(H35A,
 H35B,H35C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C),
 C47(H47A,H47B,H47C), C50(H50A,H50B,H50C), C58(H58A,H58B,H58C), C59(H59A,H59B,
 H59C), C60(H60A,H60B,H60C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              88529
_shelx_hkl_checksum              84415
_shelx_fab_checksum              72453
_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 1.237
_oxdiff_exptl_absorpt_empirical_full_min 0.840