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_4038666
_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         'C36 H36 N18 O18'
_chemical_formula_sum            'C36 H36 N18 O18'
_chemical_formula_weight         1008.83
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-05-27
_audit_creation_method
;
FinalCif V61 by Daniel Kratzert, Freiburg 2019,
https://github.com/dkratzert/FinalCif
;
_cell_angle_alpha                90
_cell_angle_beta                 108.5802(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.44200(11)
_cell_length_b                   35.5880(4)
_cell_length_c                   12.41317(17)
_cell_measurement_reflns_used    15770
_cell_measurement_temperature    100.00(12)
_cell_measurement_theta_max      71.3160
_cell_measurement_theta_min      4.2440
_cell_volume                     4791.16(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_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      100.00(12)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_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   -152.00-126.00   0.50    8.84    --  -84.25-113.00 104.00   52
  2  \w    -11.00  60.00   0.50    2.21    --    0.00  57.00 -60.00  142
  3  \w   -155.00 -80.00   0.50    8.84    --  -84.25 -19.00  60.00  150
  4  \w    -60.00 -13.00   0.50    8.84    --  -84.25  38.00  90.00   94
  5  \w     29.00  55.00   0.50    2.21    --    0.00  38.00   0.00   52
  6  \w    108.00 142.00   0.50    8.84    --   98.05 113.00-163.00   68
  7  \w     97.00 165.00   0.50    8.84    --   98.05 125.00 -90.00  136
  8  \w    115.00 160.00   0.50    8.84    --   98.05  19.00 -60.00   90
  9  \w     53.00 108.00   0.50    8.84    --   98.05-113.00 104.00  110
 10  \w    -19.00  65.00   0.50    2.21    --    0.00  77.00-180.00  168
 11  \w     85.00 111.00   0.50    8.84    --   98.05-125.00  90.00   52
 12  \w     61.00 106.00   0.50    8.84    --   98.05 -99.00  30.00   90
 13  \w     52.00 100.00   0.50    8.84    --   98.05 -99.00 -60.00   96
 14  \w     45.00 103.00   0.50    8.84    --   98.05-125.00  30.00  116
 15  \w     39.00  67.00   0.50    8.84    --   98.05 -57.00 -90.00   56
 16  \w     52.00  78.00   0.50    8.84    --   98.05 -77.00 -90.00   52
 17  \w     92.00 129.00   0.50    9.00    --   99.40 132.00  83.00   74
 18  \w     67.00  92.00   0.50    3.00    --   48.20-137.00-162.00   50
 19  \w    105.00 131.00   0.50    9.00    --   99.40 137.00 -99.00   52
 20  \w     28.00 109.00   0.50    9.00    --   99.40 -19.00-180.00  162
 21  \w     77.00 106.00   0.50    9.00    --   99.40 -99.00-150.00   58
 22  \w     55.00  80.00   0.50    3.00    --   48.20-132.00  14.00   50
 23  \w     67.00 118.00   0.50    9.00    --   99.40-137.00-162.00  102
 24  \w     35.00  60.00   0.50    9.00    --   99.40-125.00-150.00   50
 25  \w     73.00 100.00   0.50    9.00    --   99.40-125.00-150.00   54
 26  \w    -14.00  60.00   0.50    3.00    --   48.20 -57.00 -30.00  148
 27  \w     51.00 105.00   0.50    9.00    --   99.40 -99.00 -60.00  108
 28  \w     53.00  78.00   0.50    9.00    --   99.40-132.00  14.00   50
 29  \w     51.00 106.00   0.50    9.00    --   99.40 -99.00  60.00  110
 30  \w     51.00  78.00   0.50    9.00    --   99.40 -77.00  30.00   54
 31  \w     35.00  65.00   0.50    9.00    --   99.40 -57.00  60.00   60
 32  \w     27.00  56.00   0.50    9.00    --   99.40 -38.00 120.00   58
 33  \w    -80.00 -55.00   0.50    3.00    --  -48.20 137.00 -99.00   50
 34  \w     28.00  61.00   0.50    9.00    --   99.40 -38.00 150.00   66
 35  \w     28.00  67.00   0.50    9.00    --   99.40 -57.00  90.00   78
 36  \w     29.00  96.00   0.50    9.00    --   99.40 -99.00  30.00  134
 37  \w     27.00  54.00   0.50    9.00    --   99.40 -38.00 -30.00   54
 38  \w    -60.00  27.00   0.50    3.00    --  -48.20  19.00-150.00  174
 39  \w     38.00  82.00   0.50    9.00    --   99.40 -77.00 -60.00   88
 40  \w     30.00  65.00   0.50    9.00    --   99.40 -99.00-150.00   70
 41  \w     29.00  84.00   0.50    9.00    --   99.40 -77.00-150.00  110
 42  \w     10.00  37.00   0.50    3.00    --   48.20 -57.00 150.00   54
 43  \w     28.00  60.00   0.50    9.00    --   99.40 -38.00-120.00   64
 44  \w     28.00  59.00   0.50    9.00    --   99.40 -38.00-150.00   62
 45  \w     27.00  61.00   0.50    9.00    --   99.40 -38.00-180.00   68
 46  \w    -57.00  22.00   0.50    3.00    --  -48.20  38.00 -30.00  158
 47  \w    -40.00 -13.00   0.50    9.00    --  -86.25  38.00  60.00   54
 48  \w    -61.00 -29.00   0.50    9.00    --  -86.25  38.00 120.00   64
 49  \w    -59.00 -15.00   0.50    9.00    --  -86.25  38.00  90.00   88
 50  \w    -67.00 -17.00   0.50    9.00    --  -86.25  19.00 -30.00  100
 51  \w    -81.00 -56.00   0.50    9.00    --  -86.25 137.00 -99.00   50
 52  \w    -91.00 -45.00   0.50    3.00    --  -48.20 132.00  83.00   92
 53  \w   -119.00 -67.00   0.50    3.00    --  -48.20-137.00-162.00  104
 54  \w   -110.00 -68.00   0.50    9.00    --  -86.25-137.00-162.00   84
 55  \w   -138.00-111.00   0.50    9.00    --  -86.25 -99.00-120.00   54
 56  \w   -157.00 -89.00   0.50    9.00    --  -86.25 -99.00 -30.00  136
 57  \w   -119.00 -94.00   0.50    3.00    --  -48.20-132.00  14.00   50
 58  \w   -120.00 -74.00   0.50    3.00    --  -48.20-125.00  30.00   92
 59  \w   -120.00 -95.00   0.50    9.00    --  -86.25-132.00  14.00   50
 60  \w   -111.00 -73.00   0.50    3.00    --  -48.20-125.00  60.00   76
 61  \w   -162.00 -76.00   0.50    9.00    --  -86.25 -19.00-120.00  172
;
_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      0.0370167000
_diffrn_orient_matrix_UB_12      -0.0282048000
_diffrn_orient_matrix_UB_13      0.0993142000
_diffrn_orient_matrix_UB_21      -0.0286944000
_diffrn_orient_matrix_UB_22      -0.0328356000
_diffrn_orient_matrix_UB_23      -0.0853364000
_diffrn_orient_matrix_UB_31      0.1340796000
_diffrn_orient_matrix_UB_32      0.0007620000
_diffrn_orient_matrix_UB_33      -0.0014503000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_sigmaI/netI    0.0823
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9462
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.652
_diffrn_reflns_theta_min         2.483
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.989
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.581
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
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    1.399
_exptl_crystal_description       needle
_exptl_crystal_F_000             2088
_exptl_crystal_size_max          0.336
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     681
_refine_ls_number_reflns         9462
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0544P)^2^+4.0628P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1269
_refine_ls_wR_factor_ref         0.1316
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7620
_reflns_number_total             9462
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01425_si_003.cif
_cod_data_source_block           gb2020_fin
_cod_database_code               4038666
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.732
_shelx_estimated_absorpt_t_max   0.963
_chemical_oxdiff_formula         'C144  H144  N72  O72  '
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O17-C35B \\sim O17-C35A \\sim O18-C36B \\sim O18-C36A
 with sigma of 0.004
3. Rigid body (RIGU) restrains
 O18, C36B
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 O18, C36A
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
4. Others
 Fixed Sof: C35A(0.5) H35A(0.5) H35B(0.5) H35C(0.5) C35B(0.5) H35D(0.5)
 H35E(0.5) H35F(0.5) C36A(0.5) H36A(0.5) H36B(0.5) H36C(0.5) C36B(0.5)
 H36D(0.5) H36E(0.5) H36F(0.5)
5.a Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C),
 C14(H14A,H14B,H14C), C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C23(H23A,H23B,
 H23C), C26(H26A,H26B,H26C), C34(H34A,H34B,H34C), C35A(H35A,H35B,H35C),
 C35B(H35D,H35E,H35F), C36A(H36A,H36B,H36C), C36B(H36D,H36E,H36F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 1.740
_oxdiff_exptl_absorpt_empirical_full_min 0.442
_cell_oxdiff_length_a            11.44462(11)
_cell_oxdiff_length_b            35.5847(5)
_cell_oxdiff_length_c            12.41256(18)
_cell_oxdiff_angle_alpha         89.9972(12)
_cell_oxdiff_angle_beta          108.5951(11)
_cell_oxdiff_angle_gamma         90.0038(10)
_cell_oxdiff_volume              4791.16(11)
_cell_oxdiff_measurement_reflns_used 15770
_diffrn_oxdiff_digest_frames
;
0169620440760e1e62af10326ad90643e6037362566
;
_diffrn_oxdiff_digest_hkl
;
01713f1f82a44abb9191cb222a7195fefeafd4
;
_shelx_res_checksum              62899
_shelx_hkl_checksum              42586
_shelx_fab_checksum              49372