Oxidative nucleophilic aromatic amination of nitrobenzenes
V. V. Khutorianskyi; M. Sonawane; M. Posta; B. Klepetarova; P. Beier; Chem.Commun. 52 (2016) 7237–; doi:

data_7118971
_publ_section_title
;
 Oxidative nucleophilic aromatic amination of nitrobenzenes
;
_journal_name_full               Chem.Commun.
_journal_page_first              7237
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration .
_chemical_formula_moiety         'C12 H9 F5 N2 O2 S'
_chemical_formula_sum            'C12 H9 F5 N2 O2 S'
_chemical_formula_weight         340.27
_chemical_name_systematic        2-Nitro-5-(pentafluorosulfanyl)-N-phenylaniline
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_update_record
;
2015-11-25 deposited with the CCDC.
2016-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.185(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8093(3)
_cell_length_b                   10.6449(3)
_cell_length_c                   10.6262(3)
_cell_measurement_reflns_used    7337
_cell_measurement_temperature    190
_cell_measurement_theta_max      75.6080
_cell_measurement_theta_min      5.5080
_cell_volume                     1335.52(6)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      190
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.047
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11863
_diffrn_reflns_theta_full        72.026
_diffrn_reflns_theta_max         75.817
_diffrn_reflns_theta_min         5.596
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.845
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.38706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.25
_refine_ls_extinction_coef       9.9(19)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0328
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2443
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.0005988
_refine_ls_shift/su_mean         0.0000408
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 7.91 3.17 6.03 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0609
_refine_ls_wR_factor_gt          0.0538
_refine_ls_wR_factor_ref         0.0538
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2443
_reflns_number_total             2727
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.34
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_r_factor_ref   0.0404
_oxford_refine_ls_scale          5.043(13)
_oxford_reflns_number_all        2727
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file            c6cc02235a2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Other' changed to 'other'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 4609 2016-04-01 06:22:49Z antanas 
;
_cod_original_cell_volume        1335.52(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7118971
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE N   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;