Selective synthesis of β-nitrated N-heterocycles and N-nitroso-2-alkoxyamine aldehydes from inactivated cyclic amines promoted by tBuONO and oxoammonium salt
He, Yan; Zheng, Zhi; Liu, Yajie; Qiao, Jiajie; Zhang, Xinying; Fan, Xuesen; Chemical Communications  (2019) –; doi:10.1039/C9CC05963F

data_7124221
_publ_section_title
;
 Selective synthesis of \b-nitrated N-heterocycles and
 N-nitroso-2-alkoxyamine aldehydes from inactivated cyclic amines promoted
 by tBuONO and oxoammonium salt
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05963F
_journal_year                    2019
_chemical_formula_moiety         'C12 H13 F N2 O2'
_chemical_formula_sum            'C12 H13 F N2 O2'
_chemical_formula_weight         236.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-03
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_audit_update_record
;
2019-06-14 deposited with the CCDC.    2019-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.716(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3361(8)
_cell_length_b                   15.5990(14)
_cell_length_c                   7.4565(5)
_cell_measurement_reflns_used    2093
_cell_measurement_temperature    296.83(10)
_cell_measurement_theta_max      72.0370
_cell_measurement_theta_min      4.4300
_cell_volume                     1157.29(16)
_computing_cell_refinement       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.83(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6296
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_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    -82.00   5.00   1.00    1.00    --  -40.64 105.00-169.00   87
  2  \w     22.00  47.00   1.00    1.00    --   40.64-105.00  90.00   25
  3  \w    104.00 160.00   1.00    1.00    --  103.55 105.00-169.00   56
  4  \w     54.00  79.00   1.00    1.00    --  103.55-105.00  90.00   25
  5  \w   -110.00 -14.00   1.00    1.00    --  -40.64 -57.00   0.00   96
  6  \w      5.00  34.00   1.00    1.00    --   40.64 -99.00 -30.00   29
  7  \w     43.00  86.00   1.00    1.00    --   40.64-125.00  30.00   43
  8  \w    118.00 144.00   1.00    1.00    --  103.55 178.00  30.00   26
  9  \w     60.00  92.00   1.00    1.00    --  103.55 178.00  30.00   32
 10  \w     53.00 111.00   1.00    1.00    --  103.55-111.00 150.00   58
 11  \w    119.00 175.00   1.00    1.00    --  103.55  30.00   0.00   56
 12  \w     82.00 108.00   1.00    1.00    --  103.55  30.00   0.00   26
 13  \w    119.00 175.00   1.00    1.00    --  103.55 111.00 150.00   56
 14  \w    112.00 178.00   1.00    1.00    --  103.55 111.00   0.00   66
 15  \w     52.00 124.00   1.00    1.00    --  103.55 -61.00-120.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1012625000
_diffrn_orient_matrix_UB_12      0.0738083000
_diffrn_orient_matrix_UB_13      0.0620344000
_diffrn_orient_matrix_UB_21      0.1155753000
_diffrn_orient_matrix_UB_22      -0.0604929000
_diffrn_orient_matrix_UB_23      -0.0104069000
_diffrn_orient_matrix_UB_31      -0.0191386000
_diffrn_orient_matrix_UB_32      0.0253334000
_diffrn_orient_matrix_UB_33      -0.2052490000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5095
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.300
_diffrn_reflns_theta_min         4.444
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.878
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.42a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0493
_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^)+(0.0860P)^2^+0.1681P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1557
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1682
_reflns_number_total             2223
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05963f2.cif
_cod_data_source_block           hy-20190521
_cod_database_code               7124221
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_shelx_estimated_absorpt_t_max   0.917
_shelx_estimated_absorpt_t_min   0.844
_diffrn_oxdiff_digest_frames
;
011ea2e844e155620fea88e287f30c0a1900029a4f7
;
_diffrn_oxdiff_digest_hkl
;
01e33540874f2040a330716b91b5073dc8dbb1
;
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C8(H8), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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 1.324
_oxdiff_exptl_absorpt_empirical_full_min 0.796