Does electrophilic activation of nitroalkanes in polyphosphoric acid involve formation of nitrile oxides?
Aksenov, Alexander V.; Aksenov, Nicolai A.; Kirilov, Nikita K.; Skomorokhov, Anton A.; Aksenov, Dmitrii A.; Kurenkov, Igor A.; Sorokina, Elena A.; Nobi, Mezvah A.; Rubin, Michael; RSC Advances 11 (2021) 35937–35945; doi:10.1039/D1RA06503C

data_7243853
_publ_section_title
;
 Does electrophilic activation of nitroalkanes in polyphosphoric acid
 involve formation of nitrile oxides?
;
_journal_issue                   57
_journal_name_full               'RSC Advances'
_journal_page_first              35937
_journal_page_last               35945
_journal_paper_doi               10.1039/D1RA06503C
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C16 H10 F N O2'
_chemical_formula_sum            'C16 H10 F N O2'
_chemical_formula_weight         267.25
_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     dual
_audit_creation_date             2021-07-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-07-27 deposited with the CCDC.	2021-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.1230(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.77617(12)
_cell_length_b                   28.7775(6)
_cell_length_c                   7.41435(13)
_cell_measurement_reflns_used    7990
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.8930
_cell_measurement_theta_min      4.5550
_cell_volume                     1227.52(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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    'SHELXD  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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   -121.00   0.00   1.00    1.00    --  -41.35 -19.00 -60.00  121
  2  \w      6.00  82.00   1.00    1.00    --   41.35 -99.00-180.00   76
  3  \w     27.00  97.00   1.00    1.00    --   41.35-125.00   0.00   70
  4  \w     36.00 140.00   1.00    1.00    --  112.00 -30.00-120.00  104
  5  \w     30.00 106.00   1.00    1.00    --  112.00 -95.00  60.00   76
  6  \w     36.00 109.00   1.00    1.00    --  112.00-111.00 150.00   73
  7  \w     61.00 146.00   1.00    1.00    --  112.00 178.00 -60.00   85
  8  \w     36.00 109.00   1.00    1.00    --  112.00-111.00  60.00   73
  9  \w     36.00 109.00   1.00    1.00    --  112.00-111.00  30.00   73
 10  \w     36.00 109.00   1.00    1.00    --  112.00-111.00-150.00   73
 11  \w     36.00 109.00   1.00    1.00    --  112.00-111.00 120.00   73
 12  \w     39.00 138.00   1.00    1.00    --  112.00 -45.00  30.00   99
 13  \w     36.00 109.00   1.00    1.00    --  112.00-111.00-180.00   73
 14  \w     59.00 178.00   1.00    1.00    --  112.00  15.00 -30.00  119
 15  \w     83.00 178.00   1.00    1.00    --  112.00  61.00-150.00   95
 16  \w     36.00 145.00   1.00    1.00    --  112.00 -77.00-150.00  109
 17  \w     84.00 178.00   1.00    1.00    --  112.00  30.00-120.00   94
 18  \w    104.00 178.00   1.00    1.00    --  112.00 111.00 150.00   74
 19  \w     69.00 138.00   1.00    1.00    --  112.00 178.00-150.00   69
 20  \w    107.00 172.00   1.00    1.00    --  112.00 111.00  30.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2169299000
_diffrn_orient_matrix_UB_12      -0.0313253000
_diffrn_orient_matrix_UB_13      0.0092151000
_diffrn_orient_matrix_UB_21      0.1569269000
_diffrn_orient_matrix_UB_22      0.0433797000
_diffrn_orient_matrix_UB_23      0.0139656000
_diffrn_orient_matrix_UB_31      0.0038736000
_diffrn_orient_matrix_UB_32      -0.0015630000
_diffrn_orient_matrix_UB_33      0.2079661000
_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  0.0452
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            12715
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.239
_diffrn_reflns_theta_min         6.151
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.888
_exptl_absorpt_correction_T_max  0.907
_exptl_absorpt_correction_T_min  0.693
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_preparation
'Crystallized by slow evaporation of saturated solution in EtOAc.'
_exptl_crystal_recrystallization_method
'Prepared by cycloaddition reaction in PPA.'
_exptl_crystal_size_max          0.576
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2566
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0513
_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^)+(0.0730P)^2^+0.8486P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1374
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2438
_reflns_number_total             2566
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra06503c2.cif
_cod_data_source_block           anna_kur182_3
_cod_database_code               7243853
_shelx_shelxl_version_number     2018/3
_publ_section_exptl
;
Any special experimental details
;
_chemical_oxdiff_formula         C16H10FNO2
_reflns_odcompleteness_completeness 98.18
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C16(H16), C15(H15), C14(H14), C13(H13), C12(H12), C10(H10), C9(H9),
 C7(H7), C6(H6)
2.b Fitted hexagon refined as free rotating group:
 C11(C16,C15,C14,C13,C12)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              85628
_olex2_date_sample_data_collection 2021-07-03
_olex2_exptl_crystal_mounting_method
'Mounted on the glass stick by acrylic glue.'
_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 1.761
_oxdiff_exptl_absorpt_empirical_full_min 0.537