#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/66/2016609.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2016609
loop_
_publ_author_name
'Walczak, Christopher P.'
'Yonkey, Matthew M.'
'Squattrito, Philip J.'
'Mohanty, Dillip K.'
'Kirschbaum, Kristin'
_publ_section_title
;
 1,3-Bis(ethylamino)-2-nitrobenzene,
 1,3-bis(n-octylamino)-2-nitrobenzene and
 4-ethylamino-2-methyl-1H-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          'C10 H15 N3 O2'
_chemical_formula_moiety         'C10 H15 N3 O2'
_chemical_formula_sum            'C10 H15 N3 O2'
_chemical_formula_weight         209.25
_chemical_melting_point          336
_chemical_name_systematic
;
1,3-bis(n-ethylamino)-2-nitrobenzene
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.492(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.0425(6)
_cell_length_b                   9.2564(10)
_cell_length_c                   11.4901(13)
_cell_measurement_reflns_used    2623
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      33.0
_cell_measurement_theta_min      2.8
_cell_volume                     523.61(10)
_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(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART 6000 CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0548
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3016
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1017
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0463
_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/[σ²(Fo²)+(0.0413P)²+0.1845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1207
_reflns_number_gt                919
_reflns_number_total             1017
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3210.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      P2/n
_cod_database_code               2016609
_cod_database_fobs_code          2016609
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y, -z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.9243(2) 0.50417(12) 0.82181(10) 0.0410(4) Uani d . 1
N N1 0.7500 0.43516(19) 0.7500 0.0281(4) Uani d S 1
N N2 1.1793(2) 0.27164(15) 0.89937(10) 0.0268(4) Uani d . 1
C C1 0.7500 0.2823(2) 0.7500 0.0248(5) Uani d S 1
C C2 0.9703(3) 0.20475(16) 0.82619(11) 0.0239(4) Uani d . 1
C C3 0.9629(3) 0.05350(16) 0.82223(12) 0.0257(4) Uani d . 1
C C4 0.7500 -0.0188(2) 0.7500 0.0271(5) Uani d S 1
C C5 1.3992(3) 0.19564(16) 0.97807(12) 0.0262(4) Uani d . 1
C C6 1.5899(3) 0.30237(19) 1.05306(15) 0.0340(4) Uani d . 1
H H2 1.176(3) 0.363(2) 0.9019(15) 0.034(5) Uiso d . 1
H H3 1.106(3) 0.0036(17) 0.8670(15) 0.028(4) Uiso d . 1
H H4 0.7500 -0.120(3) 0.7500 0.019(5) Uiso d S 1
H H5A 1.322(3) 0.1303(19) 1.0311(15) 0.033(4) Uiso d . 1
H H5B 1.499(3) 0.1344(18) 0.9323(14) 0.030(4) Uiso d . 1
H H6C 1.737(4) 0.254(2) 1.1045(17) 0.043(5) Uiso d . 1
H H6A 1.665(4) 0.368(2) 1.0015(17) 0.048(5) Uiso d . 1
H H6B 1.497(4) 0.357(2) 1.1008(17) 0.045(5) Uiso d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0352(7) 0.0268(7) 0.0515(7) -0.0012(5) -0.0113(5) -0.0040(5)
N1 0.0236(8) 0.0272(9) 0.0322(9) 0.000 0.0030(7) 0.000
N2 0.0258(7) 0.0246(7) 0.0296(7) 0.0017(5) 0.0053(5) 0.0004(5)
C1 0.0255(10) 0.0252(11) 0.0264(10) 0.000 0.0113(8) 0.000
C2 0.0229(7) 0.0298(8) 0.0218(7) 0.0002(6) 0.0108(6) 0.0012(5)
C3 0.0270(8) 0.0278(8) 0.0244(7) 0.0041(6) 0.0100(6) 0.0028(5)
C4 0.0367(12) 0.0216(11) 0.0272(10) 0.000 0.0162(9) 0.000
C5 0.0267(8) 0.0286(8) 0.0244(7) 0.0035(6) 0.0080(6) 0.0023(6)
C6 0.0322(9) 0.0348(9) 0.0317(8) 0.0064(7) -0.0001(7) -0.0009(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O1 N1 O1 . 4_757 118.21(17)
O1 N1 C1 . . 120.90(9)
O1 N1 C1 4_757 . 120.90(9)
C2 N2 C5 . . 123.68(14)
C2 N2 H2 . . 117.3(11)
C5 N2 H2 . . 118.9(11)
N1 C1 C2 . . 119.72(10)
N1 C1 C2 . 4_757 119.72(10)
C2 C1 C2 . 4_757 120.56(19)
N2 C2 C3 . . 119.40(13)
N2 C2 C1 . . 122.95(15)
C3 C2 C1 . . 117.66(14)
C4 C3 C2 . . 121.05(14)
C4 C3 H3 . . 120.6(10)
C2 C3 H3 . . 118.3(10)
C3 C4 C3 . 4_757 122.0(2)
C3 C4 H4 . . 119.00(10)
C3 C4 H4 4_757 . 119.00(10)
N2 C5 C6 . . 110.14(13)
N2 C5 H5A . . 109.1(9)
C6 C5 H5A . . 109.5(9)
N2 C5 H5B . . 110.9(9)
C6 C5 H5B . . 110.3(9)
H5A C5 H5B . . 106.9(14)
C5 C6 H6C . . 111.0(11)
C5 C6 H6A . . 110.1(11)
H6C C6 H6A . . 108.4(16)
C5 C6 H6B . . 110.5(11)
H6C C6 H6B . . 108.0(16)
H6A C6 H6B . . 108.7(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 N1 . 1.2441(14)
N1 O1 4_757 1.2441(14)
N1 C1 . 1.415(3)
N2 C2 . 1.3483(18)
N2 C5 . 1.4520(18)
N2 H2 . 0.85(2)
C1 C2 . 1.4472(17)
C1 C2 4_757 1.4472(18)
C2 C3 . 1.401(2)
C3 C4 . 1.3795(18)
C3 H3 . 0.915(17)
C4 C3 4_757 1.3795(18)
C4 H4 . 0.93(2)
C5 C6 . 1.511(2)
C5 H5A . 0.997(18)
C5 H5B . 0.982(17)
C6 H6C . 0.95(2)
C6 H6A . 0.98(2)
C6 H6B . 0.94(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2 O1 0.85(2) 1.91(2) 2.5660(10) 133(2) yes
