#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/91/2229167.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_2229167
loop_
_publ_author_name
'Zhang, Wen-Tai'
'Zhou, Cheng-He'
'Ji, Qing-Gang'
_publ_section_title
;
 2-Chloro-N-[(4-chlorophenyl)(phenyl)methyl]-N-[2-(4-nitro-1H-imidazol-1-yl)ethyl]ethanamine
;
_journal_coeditor_code           NG5107
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o491
_journal_paper_doi               10.1107/S160053681100256X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H20 Cl2 N4 O2'
_chemical_formula_moiety         'C20 H20 Cl2 N4 O2'
_chemical_formula_sum            'C20 H20 Cl2 N4 O2'
_chemical_formula_weight         419.30
_chemical_name_systematic
;
2-Chloro-N-[(4-chlorophenyl)(phenyl)methyl]-N-[2-(4-nitro-
1H-imidazol-1-yl)ethyl]ethanamine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.802(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8206(16)
_cell_length_b                   25.005(5)
_cell_length_c                   9.0450(17)
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.286
_cell_measurement_theta_min      2.433
_cell_volume                     1959.6(6)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9838
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.238
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0528
_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/[σ²(Fo²)+(0.0576P)²+0.9040P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1388
_reflns_number_gt                2464
_reflns_number_total             3449
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng5107.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2229167
_cod_database_fobs_code          2229167
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3270(3) 0.05952(13) 0.0927(3) 0.0487(7) Uani d . 1 . .
C C2 0.4173(4) 0.01834(13) 0.1569(4) 0.0615(9) Uani d . 1 . .
H H2 0.3972 -0.0165 0.1231 0.074 Uiso calc R 1 . .
C C3 0.5385(4) 0.02915(12) 0.2723(3) 0.0538(8) Uani d . 1 . .
H H3 0.5994 0.0009 0.3161 0.065 Uiso calc R 1 . .
C C4 0.5734(3) 0.07989(11) 0.3257(3) 0.0402(6) Uani d . 1 . .
C C5 0.4771(3) 0.12070(12) 0.2588(3) 0.0498(7) Uani d . 1 . .
H H5 0.4957 0.1556 0.2933 0.060 Uiso calc R 1 . .
C C6 0.3544(3) 0.11081(12) 0.1423(3) 0.0514(8) Uani d . 1 . .
H H6 0.2917 0.1386 0.0985 0.062 Uiso calc R 1 . .
C C7 0.7143(3) 0.08861(11) 0.4496(3) 0.0401(6) Uani d . 1 . .
H H7 0.7628 0.0533 0.4654 0.048 Uiso calc R 1 . .
C C8 0.6827(3) 0.10452(10) 0.6032(3) 0.0400(6) Uani d . 1 . .
C C9 0.8038(3) 0.10174(11) 0.7245(3) 0.0456(7) Uani d . 1 . .
H H9 0.8999 0.0902 0.7091 0.055 Uiso calc R 1 . .
C C10 0.7859(4) 0.11550(12) 0.8666(3) 0.0536(8) Uani d . 1 . .
H H10 0.8695 0.1137 0.9463 0.064 Uiso calc R 1 . .
C C11 0.6439(4) 0.13203(13) 0.8913(4) 0.0592(8) Uani d . 1 . .
H H11 0.6313 0.1417 0.9875 0.071 Uiso calc R 1 . .
C C12 0.5226(4) 0.13412(14) 0.7746(4) 0.0657(9) Uani d . 1 . .
H H12 0.4263 0.1448 0.7912 0.079 Uiso calc R 1 . .
C C13 0.5415(3) 0.12044(12) 0.6309(3) 0.0538(8) Uani d . 1 . .
H H13 0.4573 0.1220 0.5518 0.065 Uiso calc R 1 . .
C C14 0.9049(3) 0.10277(13) 0.2887(3) 0.0547(8) Uani d . 1 . .
H H14A 0.9671 0.1308 0.2559 0.066 Uiso calc R 1 . .
H H14B 0.8231 0.0941 0.2046 0.066 Uiso calc R 1 . .
C C15 1.0037(4) 0.05433(13) 0.3272(4) 0.0591(8) Uani d . 1 . .
H H15A 1.0457 0.0436 0.2400 0.071 Uiso calc R 1 . .
H H15B 0.9407 0.0252 0.3526 0.071 Uiso calc R 1 . .
C C16 0.7954(3) 0.18032(11) 0.3913(3) 0.0498(7) Uani d . 1 . .
H H16A 0.7132 0.1884 0.4456 0.060 Uiso calc R 1 . .
H H16B 0.7574 0.1876 0.2855 0.060 Uiso calc R 1 . .
C C17 0.9333(4) 0.21643(13) 0.4485(3) 0.0557(8) Uani d . 1 . .
H H17A 1.0205 0.2049 0.4051 0.067 Uiso calc R 1 . .
H H17B 0.9081 0.2528 0.4158 0.067 Uiso calc R 1 . .
C C18 1.1030(3) 0.19238(12) 0.6938(4) 0.0523(8) Uani d . 1 . .
H H18 1.1775 0.1748 0.6516 0.063 Uiso calc R 1 . .
C C19 0.9802(3) 0.22472(11) 0.8478(3) 0.0479(7) Uani d . 1 . .
C C20 0.8953(3) 0.23602(11) 0.7104(4) 0.0521(8) Uani d . 1 . .
H H20 0.8017 0.2542 0.6891 0.063 Uiso calc R 1 . .
Cl Cl1 0.17478(11) 0.04618(4) -0.05458(11) 0.0835(3) Uani d . 1 . .
Cl Cl2 1.15787(10) 0.06636(4) 0.48090(12) 0.0777(3) Uani d . 1 . .
N N1 0.8356(2) 0.12352(9) 0.4102(2) 0.0412(5) Uani d . 1 . .
N N2 0.9760(3) 0.21524(9) 0.6115(3) 0.0458(6) Uani d . 1 . .
N N3 1.1106(3) 0.19743(10) 0.8388(3) 0.0538(6) Uani d . 1 . .
N N4 0.9403(4) 0.23746(13) 0.9901(4) 0.0692(8) Uani d . 1 . .
O O1 1.0250(3) 0.22177(12) 1.1050(3) 0.0897(9) Uani d . 1 . .
O O2 0.8228(4) 0.26290(15) 0.9864(4) 0.1142(12) Uani d . 1 . .
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C2 C1 C6 . . 121.1(3) ?
C2 C1 Cl1 . . 119.2(2) ?
C6 C1 Cl1 . . 119.8(2) ?
C1 C2 C3 . . 119.0(3) ?
C1 C2 H2 . . 120.5 ?
C3 C2 H2 . . 120.5 ?
C4 C3 C2 . . 122.8(3) ?
C4 C3 H3 . . 118.6 ?
C2 C3 H3 . . 118.6 ?
C3 C4 C5 . . 116.5(3) ?
C3 C4 C7 . . 119.3(2) ?
C5 C4 C7 . . 124.2(2) ?
C6 C5 C4 . . 121.8(3) ?
C6 C5 H5 . . 119.1 ?
C4 C5 H5 . . 119.1 ?
C1 C6 C5 . . 118.9(3) ?
C1 C6 H6 . . 120.6 ?
C5 C6 H6 . . 120.6 ?
N1 C7 C8 . . 109.3(2) ?
N1 C7 C4 . . 115.8(2) ?
C8 C7 C4 . . 116.5(2) ?
N1 C7 H7 . . 104.6 ?
C8 C7 H7 . . 104.6 ?
C4 C7 H7 . . 104.6 ?
C13 C8 C9 . . 117.5(3) ?
C13 C8 C7 . . 124.7(3) ?
C9 C8 C7 . . 117.8(2) ?
C10 C9 C8 . . 121.7(3) ?
C10 C9 H9 . . 119.2 ?
C8 C9 H9 . . 119.2 ?
C9 C10 C11 . . 119.8(3) ?
C9 C10 H10 . . 120.1 ?
C11 C10 H10 . . 120.1 ?
C12 C11 C10 . . 119.7(3) ?
C12 C11 H11 . . 120.2 ?
C10 C11 H11 . . 120.2 ?
C11 C12 C13 . . 120.4(3) ?
C11 C12 H12 . . 119.8 ?
C13 C12 H12 . . 119.8 ?
C8 C13 C12 . . 121.0(3) ?
C8 C13 H13 . . 119.5 ?
C12 C13 H13 . . 119.5 ?
N1 C14 C15 . . 115.1(2) ?
N1 C14 H14A . . 108.5 ?
C15 C14 H14A . . 108.5 ?
N1 C14 H14B . . 108.5 ?
C15 C14 H14B . . 108.5 ?
H14A C14 H14B . . 107.5 ?
C14 C15 Cl2 . . 111.8(2) ?
C14 C15 H15A . . 109.2 ?
Cl2 C15 H15A . . 109.2 ?
C14 C15 H15B . . 109.2 ?
Cl2 C15 H15B . . 109.2 ?
H15A C15 H15B . . 107.9 ?
N1 C16 C17 . . 112.0(2) ?
N1 C16 H16A . . 109.2 ?
C17 C16 H16A . . 109.2 ?
N1 C16 H16B . . 109.2 ?
C17 C16 H16B . . 109.2 ?
H16A C16 H16B . . 107.9 ?
N2 C17 C16 . . 111.8(2) ?
N2 C17 H17A . . 109.3 ?
C16 C17 H17A . . 109.3 ?
N2 C17 H17B . . 109.3 ?
C16 C17 H17B . . 109.3 ?
H17A C17 H17B . . 107.9 ?
N3 C18 N2 . . 113.2(3) ?
N3 C18 H18 . . 123.4 ?
N2 C18 H18 . . 123.4 ?
N3 C19 C20 . . 112.3(3) ?
N3 C19 N4 . . 121.4(3) ?
C20 C19 N4 . . 126.2(3) ?
N2 C20 C19 . . 105.0(3) ?
N2 C20 H20 . . 127.5 ?
C19 C20 H20 . . 127.5 ?
C14 N1 C16 . . 112.7(2) ?
C14 N1 C7 . . 113.5(2) ?
C16 N1 C7 . . 115.5(2) ?
C20 N2 C18 . . 106.5(2) ?
C20 N2 C17 . . 126.7(3) ?
C18 N2 C17 . . 126.8(3) ?
C18 N3 C19 . . 103.0(3) ?
O2 N4 O1 . . 125.0(3) ?
O2 N4 C19 . . 116.4(3) ?
O1 N4 C19 . . 118.5(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.364(4) ?
C1 C6 . 1.365(4) ?
C1 Cl1 . 1.737(3) ?
C2 C3 . 1.374(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.372(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.392(4) ?
C4 C7 . 1.524(4) ?
C5 C6 . 1.384(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N1 . 1.475(3) ?
C7 C8 . 1.520(4) ?
C7 H7 . 0.9800 ?
C8 C13 . 1.375(4) ?
C8 C9 . 1.382(4) ?
C9 C10 . 1.368(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.376(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.356(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.384(4) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 N1 . 1.450(4) ?
C14 C15 . 1.495(4) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 Cl2 . 1.779(3) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 N1 . 1.466(3) ?
C16 C17 . 1.525(4) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 N2 . 1.452(4) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 N3 . 1.307(4) ?
C18 N2 . 1.350(4) ?
C18 H18 . 0.9300 ?
C19 N3 . 1.353(4) ?
C19 C20 . 1.355(4) ?
C19 N4 . 1.432(4) ?
C20 N2 . 1.348(4) ?
C20 H20 . 0.9300 ?
N4 O2 . 1.211(4) ?
N4 O1 . 1.225(4) ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.6(5) ?
Cl1 C1 C2 C3 . . . . 179.4(2) ?
C1 C2 C3 C4 . . . . -0.4(5) ?
C2 C3 C4 C5 . . . . 1.3(4) ?
C2 C3 C4 C7 . . . . -177.3(3) ?
C3 C4 C5 C6 . . . . -1.3(4) ?
C7 C4 C5 C6 . . . . 177.2(3) ?
C2 C1 C6 C5 . . . . 0.6(5) ?
Cl1 C1 C6 C5 . . . . -179.4(2) ?
C4 C5 C6 C1 . . . . 0.4(5) ?
C3 C4 C7 N1 . . . . 118.5(3) ?
C5 C4 C7 N1 . . . . -60.0(3) ?
C3 C4 C7 C8 . . . . -110.9(3) ?
C5 C4 C7 C8 . . . . 70.6(3) ?
N1 C7 C8 C13 . . . . 121.7(3) ?
C4 C7 C8 C13 . . . . -11.9(4) ?
N1 C7 C8 C9 . . . . -59.8(3) ?
C4 C7 C8 C9 . . . . 166.6(2) ?
C13 C8 C9 C10 . . . . -1.6(4) ?
C7 C8 C9 C10 . . . . 179.7(3) ?
C8 C9 C10 C11 . . . . 0.7(4) ?
C9 C10 C11 C12 . . . . 0.5(5) ?
C10 C11 C12 C13 . . . . -0.9(5) ?
C9 C8 C13 C12 . . . . 1.2(4) ?
C7 C8 C13 C12 . . . . 179.8(3) ?
C11 C12 C13 C8 . . . . 0.0(5) ?
N1 C14 C15 Cl2 . . . . -58.3(3) ?
N1 C16 C17 N2 . . . . -70.4(3) ?
N3 C19 C20 N2 . . . . -0.3(3) ?
N4 C19 C20 N2 . . . . -178.3(3) ?
C15 C14 N1 C16 . . . . 156.5(3) ?
C15 C14 N1 C7 . . . . -69.7(3) ?
C17 C16 N1 C14 . . . . -83.4(3) ?
C17 C16 N1 C7 . . . . 143.8(2) ?
C8 C7 N1 C14 . . . . 163.5(2) ?
C4 C7 N1 C14 . . . . -62.6(3) ?
C8 C7 N1 C16 . . . . -64.1(3) ?
C4 C7 N1 C16 . . . . 69.8(3) ?
C19 C20 N2 C18 . . . . 0.6(3) ?
C19 C20 N2 C17 . . . . 179.6(3) ?
N3 C18 N2 C20 . . . . -0.7(3) ?
N3 C18 N2 C17 . . . . -179.7(3) ?
C16 C17 N2 C20 . . . . -70.0(4) ?
C16 C17 N2 C18 . . . . 108.8(3) ?
N2 C18 N3 C19 . . . . 0.4(3) ?
C20 C19 N3 C18 . . . . -0.1(3) ?
N4 C19 N3 C18 . . . . 178.0(3) ?
N3 C19 N4 O2 . . . . 178.6(3) ?
C20 C19 N4 O2 . . . . -3.6(5) ?
N3 C19 N4 O1 . . . . -2.0(4) ?
C20 C19 N4 O1 . . . . 175.8(3) ?
