1,3-Bis(ethylamino)-2-nitrobenzene, 1,3-bis(<i>n</i>-octylamino)-2-nitrobenzene and 4-ethylamino-2-methyl-1<i>H</i>-benzimidazole
Walczak, Christopher P.; Yonkey, Matthew M.; Squattrito, Philip J.; Mohanty, Dillip K.; Kirschbaum, Kristin; Acta Crystallographica Section C 64 (2008) o248–o251; doi:10.1107/S0108270108008275

data_2016610
_publ_section_title
;
 1,3-Bis(ethylamino)-2-nitrobenzene,
 1,3-bis(<i>n</i>-octylamino)-2-nitrobenzene and
 4-ethylamino-2-methyl-1<i>H</i>-benzimidazole
;
_journal_coeditor_code           SK3210
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o248
_journal_page_last               o251
_journal_paper_doi               10.1107/S0108270108008275
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C22 H39 N3 O2'
_chemical_formula_moiety         'C22 H39 N3 O2'
_chemical_formula_sum            'C22 H39 N3 O2'
_chemical_formula_weight         377.56
_chemical_melting_point          343
_chemical_name_systematic
;
1,3-bis(n-octylamino)-2-nitrobenzene
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 121.560(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.5603(16)
_cell_length_b                   9.1066(7)
_cell_length_c                   12.6778(10)
_cell_measurement_reflns_used    4172
_cell_measurement_temperature    140.0(10)
_cell_measurement_theta_max      32.5
_cell_measurement_theta_min      2.2
_cell_volume                     2121.0(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_computing_molecular_graphics    'Crystal Maker (Palmer, 2006)'
_computing_publication_material
'SHELXTL (Version 6.10; Sheldrick, 2008) and local programs'
_computing_structure_refinement  'SHELXTL (Version 6.10; Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Version 6.10; Sheldrick, 2008)'
_diffrn_ambient_temperature      140.0(10)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 6000 CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8645
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.281
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2568
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0538
_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^)+(0.0768P)^2^+0.9135P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1394
_refine_ls_wR_factor_ref         0.1493
_reflns_number_gt                2012
_reflns_number_total             2568
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sk3210.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               2016610
_cod_database_fobs_code          2016610