Regioselective Nitration of N-Alkyl Anilines using tert-Butyl Nitrite under Mild Condition.
Chaudhary, Priyanka; Gupta, Surabhi; Muniyappan, Nalluchamy; Sabiah, Shahulhameed; Kandasamy, Jeyakumar; The Journal of organic chemistry 84 (2019) 104–119; doi:10.1021/acs.joc.8b02377

data_4035897
_publ_section_title
;
 Regioselective Nitration of N-Alkyl Anilines using tert-Butyl Nitrite
 under Mild Condition.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              104
_journal_page_last               119
_journal_paper_doi               10.1021/acs.joc.8b02377
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C9 H7 Cl N2 O2'
_chemical_formula_sum            'C9 H7 Cl N2 O2'
_chemical_formula_weight         210.62
_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   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-11-26
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                112.463(10)
_cell_angle_beta                 95.209(9)
_cell_angle_gamma                99.616(8)
_cell_formula_units_Z            2
_cell_length_a                   6.1027(5)
_cell_length_b                   8.5357(9)
_cell_length_c                   10.1750(11)
_cell_measurement_reflns_used    1407
_cell_measurement_temperature    295
_cell_measurement_theta_max      28.9568
_cell_measurement_theta_min      3.7445
_cell_volume                     475.92(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_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, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      295
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9949
_diffrn_measured_fraction_theta_max 0.9487
_diffrn_measurement_details
;
  1 omega  -71.00  -45.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -37.0000   90.0000 26

  2 omega   -5.00   27.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178   96.0000  -80.0000 32

  3 omega  -16.00   17.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -99.0000 -180.0000 33

  4 omega  -83.00  -42.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178 -178.0000 -150.0000 41

  5 omega  -37.00   44.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178   57.0000 -180.0000 81

  6 omega  -13.00   17.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -99.0000   60.0000 30

  7 omega  -37.00   -4.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178   77.0000   60.0000 33

  8 omega  -55.00  -21.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178   96.0000  -80.0000 34

  9 omega   -1.00   87.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2147   57.0000   60.0000 88

 10 omega   14.00   41.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2147  -57.0000  -90.0000 27

 11 omega  -50.00  -14.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2147  -57.0000  -90.0000 36

 12 omega   -2.00   88.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2147   57.0000  -60.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0053051000
_diffrn_orient_matrix_UB_12      0.0836338000
_diffrn_orient_matrix_UB_13      0.0500899000
_diffrn_orient_matrix_UB_21      0.0279281000
_diffrn_orient_matrix_UB_22      0.0351869000
_diffrn_orient_matrix_UB_23      -0.0507348000
_diffrn_orient_matrix_UB_31      -0.1161917000
_diffrn_orient_matrix_UB_32      -0.0161594000
_diffrn_orient_matrix_UB_33      -0.0278542000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5163
_diffrn_reflns_theta_full        29.02
_diffrn_reflns_theta_max         29.02
_diffrn_reflns_theta_min         3.75
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
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    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2216
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0491P)^2^+0.0486P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1128
_reflns_number_gt                1587
_reflns_number_total             2216
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02377_si_001.cif
_cod_data_source_block           4an
_cod_original_cell_volume        475.92(8)
_cod_database_code               4035897
_chemical_oxdiff_formula         'C9 H7 O2 N2 Cl'
_chemical_oxdiff_usercomment     'YELLOWCOLOUR PLATE, 295K, 0.7 0.18 0.06'
_reflns_odcompleteness_completeness 99.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32