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#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/84/2228410.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228410
loop_
_publ_author_name
'Xie, Yong-Sheng'
'Dong, Wen-Liang'
'He, Li-Ping'
'Zhang, Xin-Ling'
'Zhao, Bao-Xiang'
_publ_section_title
;
 (E)-2,4-Dichloro-6-{1-[(2-chloroethyl)imino]ethyl}phenol
;
_journal_coeditor_code           IM2238
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3106
_journal_paper_doi               10.1107/S160053681004448X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C10 H10 Cl3 N O'
_chemical_formula_moiety         'C10 H10 Cl3 N O'
_chemical_formula_sum            'C10 H10 Cl3 N O'
_chemical_formula_weight         266.54
_chemical_name_systematic
;
(E)-2,4-Dichloro-6-{1-[(2-chloroethyl)imino]ethyl}phenol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 94.3760(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.5710(2)
_cell_length_b                   10.2323(2)
_cell_length_c                   7.73840(10)
_cell_measurement_reflns_used    2504
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.87
_cell_measurement_theta_min      2.43
_cell_volume                     1150.39(3)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω 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  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8253
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.43
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.768
_exptl_absorpt_correction_T_max  0.9511
_exptl_absorpt_correction_T_min  0.7617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.206
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2625
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0452P)²+0.1559P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0911
_reflns_number_gt                1940
_reflns_number_total             2625
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            im2238.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228410
_cod_database_fobs_code          2228410
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.57736(13) 0.15817(19) -0.1505(2) 0.0498(4) Uani d . 1 . .
C C2 0.61146(13) 0.0340(2) -0.1143(2) 0.0516(5) Uani d . 1 . .
H H2 0.5771 -0.0395 -0.1481 0.062 Uiso calc R 1 . .
C C3 0.69659(12) 0.02119(17) -0.0279(2) 0.0455(4) Uani d . 1 . .
C C4 0.75065(12) 0.12988(16) 0.0289(2) 0.0401(4) Uani d . 1 . .
C C5 0.71381(12) 0.25627(16) -0.0117(2) 0.0388(4) Uani d . 1 . .
C C6 0.62665(12) 0.26726(18) -0.1027(2) 0.0458(4) Uani d . 1 . .
H H6 0.6026 0.3495 -0.1303 0.055 Uiso calc R 1 . .
C C7 0.76729(12) 0.37256(16) 0.0405(2) 0.0403(4) Uani d . 1 . .
C C8 0.73432(14) 0.50736(18) -0.0072(3) 0.0559(5) Uani d . 1 . .
H H8A 0.6689 0.5122 0.0002 0.084 Uiso calc R 1 . .
H H8B 0.7487 0.5268 -0.1235 0.084 Uiso calc R 1 . .
H H8C 0.7642 0.5696 0.0710 0.084 Uiso calc R 1 . .
C C9 0.90715(13) 0.45820(17) 0.1910(2) 0.0491(4) Uani d . 1 . .
H H9A 0.8749 0.5189 0.2611 0.059 Uiso calc R 1 . .
H H9B 0.9276 0.5057 0.0925 0.059 Uiso calc R 1 . .
C C10 0.98893(13) 0.40380(19) 0.2962(2) 0.0509(5) Uani d . 1 . .
H H10A 0.9682 0.3582 0.3961 0.061 Uiso calc R 1 . .
H H10B 1.0284 0.4752 0.3382 0.061 Uiso calc R 1 . .
Cl Cl1 0.46922(4) 0.17442(7) -0.26165(8) 0.0791(2) Uani d . 1 . .
Cl Cl2 0.74236(4) -0.13318(4) 0.01161(8) 0.06643(18) Uani d . 1 . .
Cl Cl3 1.05345(3) 0.29415(5) 0.17400(7) 0.05817(16) Uani d . 1 . .
N N1 0.84464(10) 0.35378(14) 0.12961(19) 0.0418(3) Uani d D 1 . .
H H1N 0.858(3) 0.271(2) 0.146(5) 0.049(16) Uiso d PD 0.52(7) A 1
H H1O 0.855(3) 0.183(3) 0.145(6) 0.07(2) Uiso d PD 0.48(7) A 2
O O1 0.83069(9) 0.11256(12) 0.11379(18) 0.0494(3) Uani d 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
C6 C1 C2 . . 121.53(17) ?
C6 C1 Cl1 . . 119.55(15) ?
C2 C1 Cl1 . . 118.92(15) ?
C3 C2 C1 . . 118.94(17) ?
C3 C2 H2 . . 120.5 ?
C1 C2 H2 . . 120.5 ?
C2 C3 C4 . . 122.61(16) ?
C2 C3 Cl2 . . 119.69(14) ?
C4 C3 Cl2 . . 117.69(13) ?
O1 C4 C3 . . 120.31(15) ?
O1 C4 C5 . . 122.71(15) ?
C3 C4 C5 . . 116.98(15) ?
C6 C5 C4 . . 119.49(16) ?
C6 C5 C7 . . 120.94(15) ?
C4 C5 C7 . . 119.56(15) ?
C1 C6 C5 . . 120.43(17) ?
C1 C6 H6 . . 119.8 ?
C5 C6 H6 . . 119.8 ?
N1 C7 C5 . . 116.87(14) ?
N1 C7 C8 . . 121.32(16) ?
C5 C7 C8 . . 121.82(16) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N1 C9 C10 . . 110.83(15) ?
N1 C9 H9A . . 109.5 ?
C10 C9 H9A . . 109.5 ?
N1 C9 H9B . . 109.5 ?
C10 C9 H9B . . 109.5 ?
H9A C9 H9B . . 108.1 ?
C9 C10 Cl3 . . 112.06(12) ?
C9 C10 H10A . . 109.2 ?
Cl3 C10 H10A . . 109.2 ?
C9 C10 H10B . . 109.2 ?
Cl3 C10 H10B . . 109.2 ?
H10A C10 H10B . . 107.9 ?
C7 N1 C9 . . 124.26(15) ?
C7 N1 H1N . . 113(3) ?
C9 N1 H1N . . 122(3) ?
C4 O1 H1O . . 112(4) ?
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 C6 . 1.363(3) ?
C1 C2 . 1.385(3) ?
C1 Cl1 . 1.7446(19) ?
C2 C3 . 1.370(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.413(2) ?
C3 Cl2 . 1.7326(18) ?
C4 O1 . 1.306(2) ?
C4 C5 . 1.426(2) ?
C5 C6 . 1.409(2) ?
C5 C7 . 1.462(2) ?
C6 H6 . 0.9300 ?
C7 N1 . 1.290(2) ?
C7 C8 . 1.498(2) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 N1 . 1.460(2) ?
C9 C10 . 1.498(3) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 Cl3 . 1.781(2) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
N1 H1N . 0.874(19) ?
O1 H1O . 0.827(19) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1N O1 . 0.88(2) 1.68(2) 2.479(2) 150(4)
C10 H10B O1 2_755 0.97 2.48 3.416(2) 159
C10 H10A Cl3 4_566 0.97 2.86 3.621(2) 136
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 . . . . 0.2(3) ?
Cl1 C1 C2 C3 . . . . 179.64(14) ?
C1 C2 C3 C4 . . . . 1.1(3) ?
C1 C2 C3 Cl2 . . . . -177.60(14) ?
C2 C3 C4 O1 . . . . 178.66(16) ?
Cl2 C3 C4 O1 . . . . -2.6(2) ?
C2 C3 C4 C5 . . . . -1.6(3) ?
Cl2 C3 C4 C5 . . . . 177.17(12) ?
O1 C4 C5 C6 . . . . -179.54(15) ?
C3 C4 C5 C6 . . . . 0.7(2) ?
O1 C4 C5 C7 . . . . 0.9(3) ?
C3 C4 C5 C7 . . . . -178.81(15) ?
C2 C1 C6 C5 . . . . -1.1(3) ?
Cl1 C1 C6 C5 . . . . 179.53(13) ?
C4 C5 C6 C1 . . . . 0.5(3) ?
C7 C5 C6 C1 . . . . -179.91(16) ?
C6 C5 C7 N1 . . . . 177.17(15) ?
C4 C5 C7 N1 . . . . -3.3(2) ?
C6 C5 C7 C8 . . . . -3.0(3) ?
C4 C5 C7 C8 . . . . 176.56(16) ?
N1 C9 C10 Cl3 . . . . 60.56(18) ?
C5 C7 N1 C9 . . . . 179.36(15) ?
C8 C7 N1 C9 . . . . -0.5(3) ?
C10 C9 N1 C7 . . . . 177.78(16) ?
