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_4519194
_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 K2 N7 O10'
_chemical_formula_sum            'C5 H K2 N7 O10'
_chemical_formula_weight         397.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-12
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2021.04.04 svn.r0348f7ac for OlexSys, GUI svn.r6303)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0151(4)
_cell_length_b                   9.5909(3)
_cell_length_c                   9.1204(3)
_cell_measurement_reflns_used    5536
_cell_measurement_temperature    99.97(18)
_cell_measurement_theta_max      33.5480
_cell_measurement_theta_min      2.5570
_cell_volume                     1225.94(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution
'SHELXT 2018/3 (Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(18)
_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 0.879
_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    -15.00  28.00   0.50    2.46    --   13.08 -57.00  90.00   86
  2  \w      3.00  29.00   0.50    2.46    --   13.08 -77.00  90.00   52
  3  \w     -5.00  20.00   0.50    2.46    --   13.08-103.00 -12.00   50
  4  \w      1.00  27.00   0.50    2.46    --   13.08 -57.00-120.00   52
  5  \w    -39.00  -8.00   0.50    2.46    --  -13.55 -37.00  90.00   62
  6  \w    -84.00 -21.00   0.50    2.46    --  -13.55 -34.00-167.00  126
;
_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      -0.0005920000
_diffrn_orient_matrix_UB_12      0.0552891000
_diffrn_orient_matrix_UB_13      -0.0516403000
_diffrn_orient_matrix_UB_21      0.0219144000
_diffrn_orient_matrix_UB_22      0.0445591000
_diffrn_orient_matrix_UB_23      0.0521877000
_diffrn_orient_matrix_UB_31      0.0455930000
_diffrn_orient_matrix_UB_32      -0.0207236000
_diffrn_orient_matrix_UB_33      -0.0256926000
_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  0.0422
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8907
_diffrn_reflns_point_group_measured_fraction_full 0.889
_diffrn_reflns_point_group_measured_fraction_max 0.727
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.622
_diffrn_reflns_theta_min         2.573
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.855
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.646
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (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    2.153
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Flack x determined using 1106 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3522
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0289P)^2^+0.1095P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0730
_reflns_Friedel_coverage         0.571
_reflns_Friedel_fraction_full    0.761
_reflns_Friedel_fraction_max     0.558
_reflns_number_gt                3305
_reflns_number_total             3522
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            am1c21510_si_002.cif
_cod_data_source_block           js421a
_cod_original_cell_volume        1225.94(6)
_cod_database_code               4519194
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C5HN7O10K2
_chemical_oxdiff_usercomment     JS167
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_olex2_refinement_description
;
;
_shelx_res_checksum              46404
_shelx_hkl_checksum              55747
_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 JS167
_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 1.118
_oxdiff_exptl_absorpt_empirical_full_min 0.925