Pushing the Limit of Nitro Groups on a Pyrazole Ring with Energy-Stability Balance.
Singh, Jatinder; Staples, Richard J.; Shreeve, Jean'ne M.; ACS applied materials & interfaces 13 (2021) 61357–61364; doi:10.1021/acsami.1c21510

data_4519195
_publ_section_title
;
 Pushing the Limit of Nitro Groups on a Pyrazole Ring with
 Energy-Stability Balance.
;
_journal_issue                   51
_journal_name_full               'ACS applied materials &amp; interfaces'
_journal_page_first              61357
_journal_page_last               61364
_journal_paper_doi               10.1021/acsami.1c21510
_journal_volume                  13
_journal_year                    2021
_chemical_formula_moiety         'C5 H N7 O10, 2(H5 N2)'
_chemical_formula_sum            'C5 H11 N11 O10'
_chemical_formula_weight         385.25
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2021-07-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                60.694(5)
_cell_angle_beta                 69.675(4)
_cell_angle_gamma                70.204(4)
_cell_formula_units_Z            2
_cell_length_a                   8.7988(3)
_cell_length_b                   9.7297(4)
_cell_length_c                   9.9474(5)
_cell_measurement_reflns_used    6192
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      78.6820
_cell_measurement_theta_min      5.2140
_cell_volume                     681.40(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.973
_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    -77.00 -28.00   0.50    0.76    --  -47.36 108.00 176.00   98
  2  \w     23.00  79.00   0.50    0.76    --   47.36-108.00  79.00  112
  3  \w   -148.00-121.00   0.50    3.02    --  -91.75-108.00  79.00   54
  4  \w    -73.00 -48.00   0.50    3.02    --  -91.75 108.00 176.00   50
  5  \w     78.00 105.00   0.50    3.02    --  113.25-108.00  79.00   54
  6  \w    106.00 161.00   0.50    3.02    --  113.25 108.00 176.00  110
  7  \w    -62.00  13.00   0.50    0.76    --  -47.36  57.00 120.00  150
  8  \w    -21.00  26.00   0.50    0.76    --  -47.36  19.00-120.00   94
  9  \w    -61.00  14.00   0.50    0.76    --  -47.36  57.00-150.00  150
 10  \w    -24.00  28.00   0.50    0.76    --  -47.36  19.00-180.00  104
 11  \w    -20.00   6.00   0.50    0.76    --  -47.36  19.00 -30.00   52
 12  \w    -23.00  26.00   0.50    0.76    --  -47.36  19.00  90.00   98
 13  \w    -17.00  19.00   0.50    0.76    --   47.36 -19.00   0.00   72
 14  \w    -25.00  24.00   0.50    0.76    --   47.36 -19.00  30.00   98
 15  \w    -52.00 -27.00   0.50    3.02    --  -91.75  45.00  60.00   50
 16  \w   -163.00-127.00   0.50    3.02    --  -91.75 -94.00-150.00   72
 17  \w   -141.00 -97.00   0.50    3.02    --  -91.75 -15.00 120.00   88
 18  \w   -163.00-138.00   0.50    3.02    --  -91.75 -45.00 -90.00   50
 19  \w   -158.00-133.00   0.50    3.02    --  -91.75 -45.00-150.00   50
 20  \w     44.00  70.00   0.50    3.02    --  113.25 -61.00 150.00   52
 21  \w     47.00  75.00   0.50    3.02    --  113.25 -77.00  60.00   56
 22  \w     43.00  70.00   0.50    3.02    --  113.25 -61.00   0.00   54
 23  \w    129.00 169.00   0.50    3.02    --  113.25  45.00   0.00   80
 24  \w     71.00 101.00   0.50    3.02    --  113.25 -94.00 -90.00   60
 25  \w     42.00  69.00   0.50    3.02    --  113.25-125.00-180.00   54
 26  \w     44.00  70.00   0.50    3.02    --  113.25 -61.00-120.00   52
 27  \w     42.00  68.00   0.50    3.02    --  113.25 -94.00-180.00   52
 28  \w     79.00 104.00   0.50    3.02    --  113.25 -94.00-120.00   50
 29  \w     74.00 103.00   0.50    3.02    --  113.25 -94.00-180.00   58
 30  \w    123.00 175.00   0.50    3.02    --  113.25  45.00 -90.00  104
 31  \w     43.00  69.00   0.50    3.02    --  113.25 -94.00 -90.00   52
 32  \w    103.00 131.00   0.50    3.02    --  113.25  30.00 150.00   56
 33  \w    134.00 162.00   0.50    3.02    --  113.25  61.00  60.00   56
 34  \w     42.00  68.00   0.50    3.02    --  113.25 -94.00 -60.00   52
 35  \w     79.00 104.00   0.50    3.02    --  113.25 -94.00 -60.00   50
 36  \w     55.00 102.00   0.50    3.02    --  113.25 -94.00   0.00   94
 37  \w     42.00  67.00   0.50    3.02    --  113.25 -61.00  90.00   50
 38  \w    122.00 164.00   0.50    3.02    --  113.25  45.00-120.00   84
 39  \w     45.00  70.00   0.50    3.02    --  113.25 -61.00 -90.00   50
 40  \w    146.00 172.00   0.50    3.02    --  113.25  61.00 -30.00   52
 41  \w     77.00 103.00   0.50    3.02    --  113.25 -94.00 150.00   52
 42  \w     49.00  75.00   0.50    3.02    --  113.25 -94.00 150.00   52
 43  \w     44.00  70.00   0.50    3.02    --  113.25 -61.00-180.00   52
 44  \w    123.00 178.00   0.50    3.02    --  113.25  45.00  90.00  110
 45  \w     60.00  93.00   0.50    3.02    --  113.25 -77.00   0.00   66
 46  \w     43.00  69.00   0.50    3.02    --  113.25 -61.00 -30.00   52
 47  \w    123.00 150.00   0.50    3.02    --  113.25  45.00  60.00   54
 48  \w     43.00  69.00   0.50    3.02    --  113.25 -94.00-120.00   52
 49  \w     54.00 102.00   0.50    3.02    --  113.25 -94.00 -30.00   96
 50  \w     44.00  69.00   0.50    3.02    --  113.25 -94.00 120.00   50
 51  \w     71.00 102.00   0.50    3.02    --  113.25 -94.00 120.00   62
 52  \w    130.00 170.00   0.50    3.02    --  113.25  61.00 -60.00   80
 53  \w     46.00  71.00   0.50    3.02    --  113.25 -94.00  60.00   50
 54  \w     79.00 104.00   0.50    3.02    --  113.25 -94.00  60.00   50
 55  \w    123.00 155.00   0.50    3.02    --  113.25  45.00-150.00   64
 56  \w     45.00  70.00   0.50    3.02    --  113.25 -61.00 120.00   50
 57  \w     42.00  70.00   0.50    3.02    --  113.25 -61.00  60.00   56
 58  \w     52.00 104.00   0.50    3.02    --  113.25 -94.00-150.00  104
 59  \w    125.00 164.00   0.50    3.02    --  113.25  45.00  30.00   78
 60  \w    152.00 178.00   0.50    3.02    --  113.25  30.00 150.00   52
 61  \w    107.00 147.00   0.50    3.02    --  113.25  30.00 -30.00   80
 62  \w     44.00  69.00   0.50    3.02    --  113.25 -61.00-150.00   50
 63  \w    150.00 175.00   0.50    3.02    --  113.25  61.00 120.00   50
 64  \w    127.00 161.00   0.50    3.02    --  113.25  77.00 150.00   68
 65  \w     79.00 104.00   0.50    3.02    --  113.25 -94.00  90.00   50
 66  \w     79.00 104.00   0.50    3.02    --  113.25 -77.00 120.00   50
 67  \w     42.00  69.00   0.50    3.02    --  113.25 -61.00 -60.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0649887026
_diffrn_orient_matrix_UB_12      -0.1793176220
_diffrn_orient_matrix_UB_13      0.0988579535
_diffrn_orient_matrix_UB_21      0.0566611723
_diffrn_orient_matrix_UB_22      0.0466745428
_diffrn_orient_matrix_UB_23      0.0995992821
_diffrn_orient_matrix_UB_31      -0.1702241810
_diffrn_orient_matrix_UB_32      -0.0100224706
_diffrn_orient_matrix_UB_33      0.1160732942
_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  0.0388
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9345
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.863
_diffrn_reflns_theta_min         5.229
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.585
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.459
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.878
_exptl_crystal_description       needle
_exptl_crystal_F_000             396
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.261
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         2896
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0589
_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^)+(0.1016P)^2^+0.9556P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1768
_refine_ls_wR_factor_ref         0.1787
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2659
_reflns_number_total             2896
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            am1c21510_si_003.cif
_cod_data_source_block           js721e
_cod_database_code               4519195
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C5H11N11O10
_chemical_oxdiff_usercomment     JS167B
_reflns_odcompleteness_completeness 98.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All H(H,H) groups
2. Restrained distances
 H10B-H10A
 1.39 with sigma of 0.02
 N10-H10A = N10-H10B
 0.93 with sigma of 0.02
 N11-H11B \\sim N11-H11A \\sim N11-H11C \\sim N8-H8A \\sim N8-H8B \\sim N9-H9C
\\sim N9-H9B \\sim N9-H9A ~
 N1-H1
 with sigma of 0.02
;
_shelx_res_checksum              81330
_shelx_hkl_checksum              4180
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id JS167B
_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 1.856
_oxdiff_exptl_absorpt_empirical_full_min 0.417