#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/41/2014110.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_2014110
loop_
_publ_author_name
'Xiu-Li You '
'Cheng-Rong Lu'
'Yong Zhang'
'De-Chun Zhang'
_publ_section_title
;
 C---H···π, π--π and
 C---H···Cl interactions in chloro-substituted
 Schiff bases and
 4-chloro-N-[4-(dimethylamino)benzylidene]aniline
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o693
_journal_page_last               o695
_journal_paper_doi               10.1107/S0108270104017871
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C15 H15 Cl N2'
_chemical_formula_moiety         'C15 H15 Cl N2'
_chemical_formula_sum            'C15 H15 Cl N2'
_chemical_formula_weight         258.74
_chemical_melting_point          378
_chemical_name_systematic
;
4-chloro-N-[4-(dimethylamino)benzylidene]aniline
;
_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                 119.904(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.852(6)
_cell_length_b                   16.268(9)
_cell_length_c                   9.512(6)
_cell_measurement_reflns_used    3935
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.4835
_cell_measurement_theta_min      3.4588
_cell_volume                     1321.5(14)
_computing_cell_refinement       CrystalClear
_computing_data_collection
;
CrystalClear (Rigaku/MSC, 2001)
;
_computing_data_reduction
;
CrystalStructure (Rigaku/MSC & Rigaku Corporation, 2001)
;
_computing_molecular_graphics    reference?
_computing_publication_material  reference?
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  ' Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10180
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.46
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  0.9228
_exptl_absorpt_correction_T_min  0.8323
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.70
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.228
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2956
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0555
_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)+(0.0677P)²+0.3993P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1401
_refine_ls_wR_factor_ref         0.1433
_reflns_number_gt                2773
_reflns_number_total             2956
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            de1245.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               2014110
_cod_database_fobs_code          2014110
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_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
_atom_site_type_symbol
Cl1 0.89087(6) 0.37831(4) 0.21784(6) 0.0580(2) Uani d . 1 . . Cl
N1 0.60073(17) 0.38891(8) 0.63361(17) 0.0362(3) Uani d . 1 . . N
N2 0.18129(18) 0.37376(10) 0.97868(17) 0.0417(4) Uani d . 1 . . N
C1 0.40283(18) 0.35404(9) 0.69945(19) 0.0340(4) Uani d . 1 . . C
C2 0.47823(19) 0.38991(10) 0.8534(2) 0.0356(4) Uani d . 1 . . C
H2 0.5813 0.4108 0.8951 0.043 Uiso calc R 1 . . H
C3 0.40763(19) 0.39577(10) 0.94605(19) 0.0351(4) Uani d . 1 . . C
H3 0.4632 0.4197 1.0509 0.042 Uiso calc R 1 . . H
C4 0.25288(19) 0.36664(9) 0.88783(19) 0.0335(3) Uani d . 1 . . C
C5 0.17790(19) 0.32941(10) 0.7333(2) 0.0385(4) Uani d . 1 . . C
H5 0.0748 0.3084 0.6905 0.046 Uiso calc R 1 . . H
C6 0.2521(2) 0.32317(10) 0.6435(2) 0.0389(4) Uani d . 1 . . C
H6 0.1993 0.2971 0.5405 0.047 Uiso calc R 1 . . H
C7 0.47312(19) 0.35135(10) 0.5968(2) 0.0356(4) Uani d . 1 . . C
H7 0.4226 0.3206 0.4989 0.043 Uiso calc R 1 . . H
C8 0.66290(18) 0.38361(9) 0.52806(19) 0.0324(3) Uani d . 1 . . C
C9 0.66878(19) 0.31082(10) 0.4542(2) 0.0382(4) Uani d . 1 . . C
H9 0.6249 0.2620 0.4696 0.046 Uiso calc R 1 . . H
C10 0.7380(2) 0.30911(11) 0.3584(2) 0.0416(4) Uani d . 1 . . C
H10 0.7420 0.2593 0.3083 0.050 Uiso calc R 1 . . H
C11 0.80115(19) 0.38026(11) 0.3362(2) 0.0389(4) Uani d . 1 . . C
C12 0.7964(2) 0.45362(10) 0.4078(2) 0.0403(4) Uani d . 1 . . C
H12 0.8390 0.5025 0.3906 0.048 Uiso calc R 1 . . H
C13 0.7288(2) 0.45433(10) 0.5045(2) 0.0381(4) Uani d . 1 . . C
H13 0.7272 0.5040 0.5561 0.046 Uiso calc R 1 . . H
C14 0.0142(2) 0.36234(16) 0.9064(3) 0.0590(6) Uani d . 1 . . C
H14A -0.0407 0.4069 0.8292 0.089 Uiso calc R 1 . . H
H14B -0.0143 0.3629 0.9914 0.089 Uiso calc R 1 . . H
H14C -0.0157 0.3095 0.8495 0.089 Uiso calc R 1 . . H
C15 0.2598(3) 0.41126(16) 1.1376(2) 0.0572(5) Uani d . 1 . . C
H15A 0.3671 0.3903 1.1992 0.086 Uiso calc R 1 . . H
H15B 0.2032 0.3979 1.1951 0.086 Uiso calc R 1 . . H
H15C 0.2621 0.4710 1.1263 0.086 Uiso calc R 1 . . H
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C8 119.36(14) y
C4 N2 C14 120.87(16) y
C4 N2 C15 121.45(15) y
C14 N2 C15 116.13(17) y
C6 C1 C2 117.26(16) y
C6 C1 C7 120.36(15) y
C2 C1 C7 122.33(15) y
C3 C2 C1 121.85(15) ?
C3 C2 H2 119.1 ?
C1 C2 H2 119.1 ?
C2 C3 C4 121.10(15) ?
C2 C3 H3 119.5 ?
C4 C3 H3 119.5 ?
N2 C4 C5 121.90(15) y
N2 C4 C3 121.19(15) y
C5 C4 C3 116.90(16) y
C6 C5 C4 120.90(16) ?
C6 C5 H5 119.5 ?
C4 C5 H5 119.5 ?
C5 C6 C1 121.95(15) ?
C5 C6 H6 119.0 ?
C1 C6 H6 119.0 ?
N1 C7 C1 122.31(15) y
N1 C7 H7 118.8 ?
C1 C7 H7 118.8 ?
C13 C8 C9 118.75(16) y
C13 C8 N1 117.70(14) y
C9 C8 N1 123.46(14) y
C10 C9 C8 120.50(16) ?
C10 C9 H9 119.8 ?
C8 C9 H9 119.8 ?
C11 C10 C9 119.46(16) ?
C11 C10 H10 120.3 ?
C9 C10 H10 120.3 ?
C10 C11 C12 121.24(17) y
C10 C11 Cl1 119.74(14) y
C12 C11 Cl1 119.01(14) y
C13 C12 C11 118.75(16) ?
C13 C12 H12 120.6 ?
C11 C12 H12 120.6 ?
C12 C13 C8 121.28(15) ?
C12 C13 H13 119.4 ?
C8 C13 H13 119.4 ?
N2 C14 H14A 109.5 ?
N2 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
N2 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
N2 C15 H15A 109.5 ?
N2 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
N2 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
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
Cl1 C11 . 1.744(2) y
N1 C7 . 1.280(2) y
N1 C8 . 1.415(2) y
N2 C4 . 1.366(2) y
N2 C14 . 1.445(3) y
N2 C15 . 1.445(3) y
C1 C6 . 1.397(2) ?
C1 C2 . 1.397(2) ?
C1 C7 . 1.452(2) y
C2 C3 . 1.371(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.419(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.411(2) ?
C5 C6 . 1.377(3) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 C13 . 1.393(2) ?
C8 C9 . 1.393(2) ?
C9 C10 . 1.384(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.379(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.387(2) ?
C12 C13 . 1.379(3) ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
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
_geom_hbond_publ_flag
C14 H14B Cl1 1_456 0.979 2.753 3.729(3) 174.5 y
C2 H2 Cl1 1_556 0.950 3.110 3.812(3) 132.0 y
C6 H6 N2 4_565 0.950 2.828 3.481(3) 126.8 y
C14 H14A N1 1_455 0.981 3.078 3.602(4) 114.9 y
C10 H10 N1 4_565 0.951 2.865 3.728(3) 151.5 y
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
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.8(2) ?
C7 C1 C2 C3 176.70(14) y
C1 C2 C3 C4 -1.1(2) ?
C14 N2 C4 C5 -15.4(3) y
C15 N2 C4 C5 179.36(18) y
C14 N2 C4 C3 165.29(18) y
C15 N2 C4 C3 0.1(3) y
C2 C3 C4 N2 -178.80(15) ?
C2 C3 C4 C5 1.9(2) ?
N2 C4 C5 C6 179.76(15) ?
C3 C4 C5 C6 -0.9(2) ?
C4 C5 C6 C1 -0.9(3) ?
C2 C1 C6 C5 1.7(2) ?
C7 C1 C6 C5 -175.78(15) y
C8 N1 C7 C1 179.93(13) y
C6 C1 C7 N1 170.00(16) y
C2 C1 C7 N1 -7.4(2) y
C7 N1 C8 C13 140.53(16) y
C7 N1 C8 C9 -43.0(2) y
C13 C8 C9 C10 -0.4(2) ?
N1 C8 C9 C10 -176.86(15) y
C8 C9 C10 C11 -0.1(2) ?
C9 C10 C11 C12 -0.1(3) ?
C9 C10 C11 Cl1 179.16(12) ?
C10 C11 C12 C13 0.9(3) ?
Cl1 C11 C12 C13 -178.39(12) ?
C11 C12 C13 C8 -1.4(2) ?
C9 C8 C13 C12 1.2(2) ?
N1 C8 C13 C12 177.87(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652391
