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_2019206
_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         'C22 H22 N4 O4'
_chemical_formula_sum            'C22 H22 N4 O4'
_chemical_formula_weight         406.44
_chemical_melting_point          408
_chemical_name_common
2,4-dinitro-1,5-bis-N-(2-phenylethyl)aminobenzene
_chemical_name_systematic
;
4,6-Dinitro-<i>N</i>,<i>N</i>'-bis(2-phenylethyl)benzene-1,3-diamine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                93.4660(10)
_cell_angle_beta                 106.5950(10)
_cell_angle_gamma                106.9320(10)
_cell_formula_units_Z            2
_cell_length_a                   8.1121(7)
_cell_length_b                   10.1819(8)
_cell_length_c                   13.1018(11)
_cell_measurement_reflns_used    17364
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.65
_cell_measurement_theta_min      2.468
_cell_volume                     979.88(14)
_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 1.000
_diffrn_measured_fraction_theta_max 0.928
_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  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17364
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         33.03
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_correction_T_min  0.9809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelpiped
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.206
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         6868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0693P)^2^+0.1480P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1207
_reflns_number_gt                5289
_reflns_number_total             6868
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            cu3041.cif
_cod_data_source_block           C22H22N4O4
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2019206