A series of <i>N</i>-(2-phenylethyl)nitroaniline derivatives as precursors for slow and sustained nitric oxide release agents
Wade, Colin B.; Mohanty, Dillip K.; Squattrito, Philip J.; Amato, Nicholas J.; Kirschbaum, Kristin; Acta Crystallographica Section C 69 (2013) 1383–1389; doi:10.1107/S0108270113025869

data_2019208
_publ_section_title
;
 A series of <i>N</i>-(2-phenylethyl)nitroaniline derivatives as
 precursors for slow and sustained nitric oxide release agents
;
_journal_coeditor_code           CU3041
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1383
_journal_page_last               1389
_journal_paper_doi               10.1107/S0108270113025869
_journal_volume                  69
_journal_year                    2013
_chemical_formula_moiety         'C15 H16 N2 O4 S'
_chemical_formula_sum            'C15 H16 N2 O4 S'
_chemical_formula_weight         320.36
_chemical_melting_point          414
_chemical_name_common
4-(methylsulfonyl)-2-nitro-N-(2-phenylethyl)aniline
_chemical_name_systematic
;
4-(methylsulfonyl)-2-nitro-<i>N</i>-(2-phenylethyl)aniline
;
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   20.4639(13)
_cell_length_b                   20.4639(13)
_cell_length_c                   14.3952(14)
_cell_measurement_reflns_used    53474
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.86
_cell_measurement_theta_min      2.63
_cell_volume                     6028.3(8)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_molecular_graphics    'CrystalMaker (Palmer, 2013)'
_computing_publication_material  'APEX2 (Bruker, 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX DUO CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0090
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            52424
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         32.92
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.9546
_exptl_absorpt_correction_T_min  0.9120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cuboid
_exptl_crystal_F_000             2688
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.306
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         5524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0290
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0494P)^2^+3.0117P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0863
_reflns_number_gt                5155
_reflns_number_total             5524
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            cu3041.cif
_cod_data_source_block           C15H16N2O4S
_cod_original_cell_volume        6028.3(10)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               2019208