#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/17/2211700.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_2211700
loop_
_publ_author_name
'Yang, Shu-Ping'
'Han, Li-Jun'
'Wang, Da-Qi'
'Xia, Hai-Tao'
_publ_section_title
;
 N,N'-Bis(4-chlorobenzylidene)propane-1,2-diamine
;
_journal_coeditor_code           AT2174
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o141
_journal_page_last               o143
_journal_paper_doi               10.1107/S160053680605183X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C17 H16 Cl2 N2'
_chemical_formula_moiety         'C17 H16 Cl2 N2'
_chemical_formula_sum            'C17 H16 Cl2 N2'
_chemical_formula_weight         319.22
_chemical_melting_point          350
_chemical_name_systematic
;
N,N'-Bis(4-chlorobenzylidene)propane-1,2-diamine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                81.031(3)
_cell_angle_beta                 72.354(2)
_cell_angle_gamma                82.339(3)
_cell_formula_units_Z            2
_cell_length_a                   7.731(3)
_cell_length_b                   9.301(3)
_cell_length_c                   11.970(3)
_cell_measurement_reflns_used    1262
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.268
_cell_measurement_theta_min      2.233
_cell_volume                     806.8(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Siemens SMART 1000 CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4174
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.80
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.397
_exptl_absorpt_correction_T_max  0.9284
_exptl_absorpt_correction_T_min  0.8025
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2794
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0446
_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)+(0.0349P)²+0.2563P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.1152
_reflns_number_gt                1704
_reflns_number_total             2794
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2174.cif
_cod_data_source_block           I
_cod_database_code               2211700
_cod_database_fobs_code          2211700
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cl Cl1 0.34835(11) 0.65472(11) 0.29418(7) 0.0814(3) Uani d . 1
Cl Cl2 0.63709(14) -0.06389(10) 1.12015(9) 0.0984(4) Uani d . 1
N N1 0.8410(3) 0.7925(2) 0.64059(19) 0.0515(6) Uani d . 1
N N2 0.9132(3) 0.5945(3) 0.8465(2) 0.0534(6) Uani d . 1
C C1 0.8769(4) 0.7224(3) 0.5533(2) 0.0501(7) Uani d . 1
H H1 0.9938 0.6765 0.5272 0.060 Uiso calc R 1
C C2 0.7447(4) 0.7087(3) 0.4899(2) 0.0462(7) Uani d . 1
C C3 0.5743(4) 0.7858(3) 0.5139(2) 0.0559(7) Uani d . 1
H H3 0.5407 0.8487 0.5717 0.067 Uiso calc R 1
C C4 0.4535(4) 0.7700(3) 0.4529(2) 0.0619(8) Uani d . 1
H H4 0.3400 0.8234 0.4684 0.074 Uiso calc R 1
C C5 0.5023(4) 0.6751(3) 0.3695(2) 0.0549(7) Uani d . 1
C C6 0.6710(4) 0.5992(3) 0.3422(2) 0.0596(8) Uani d . 1
H H6 0.7036 0.5365 0.2844 0.072 Uiso calc R 1
C C7 0.7921(4) 0.6177(3) 0.4023(2) 0.0566(8) Uani d . 1
H H7 0.9078 0.5679 0.3833 0.068 Uiso calc R 1
C C8 0.8004(4) 0.5522(3) 0.9424(2) 0.0505(7) Uani d . 1
H H8 0.7351 0.6228 0.9901 0.061 Uiso calc R 1
C C9 0.8641(4) 0.2859(3) 0.9251(2) 0.0522(7) Uani d . 1
H H9 0.9585 0.3057 0.8565 0.063 Uiso calc R 1
C C10 0.8261(4) 0.1438(3) 0.9657(2) 0.0588(8) Uani d . 1
H H10 0.8935 0.0679 0.9248 0.071 Uiso calc R 1
C C11 0.6868(4) 0.1150(3) 1.0679(3) 0.0565(8) Uani d . 1
C C12 0.5870(4) 0.2247(4) 1.1290(2) 0.0577(8) Uani d . 1
H H12 0.4939 0.2038 1.1979 0.069 Uiso calc R 1
C C13 0.6256(4) 0.3667(3) 1.0877(2) 0.0550(7) Uani d . 1
H H13 0.5578 0.4419 1.1293 0.066 Uiso calc R 1
C C14 0.7647(3) 0.3997(3) 0.9843(2) 0.0449(7) Uani d . 1
C C15 0.9896(4) 0.8019(3) 0.6909(2) 0.0513(7) Uani d . 1
H H15 1.0973 0.7404 0.6517 0.062 Uiso calc R 1
C C16 0.9342(4) 0.7509(3) 0.8212(2) 0.0551(7) Uani d . 1
H H16A 1.0256 0.7726 0.8550 0.066 Uiso calc R 1
H H16B 0.8198 0.8043 0.8584 0.066 Uiso calc R 1
C C17 1.0344(5) 0.9603(3) 0.6686(3) 0.0717(9) Uani d . 1
H H17A 1.0746 0.9903 0.5851 0.108 Uiso calc R 1
H H17B 1.1293 0.9691 0.7028 0.108 Uiso calc R 1
H H17C 0.9276 1.0214 0.7038 0.108 Uiso calc R 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'
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
_geom_angle_publ_flag
C1 N1 C15 117.5(2) y
C8 N2 C16 116.7(3) y
N1 C1 C2 123.9(3) y
N1 C1 H1 118.0 ?
C2 C1 H1 118.0 ?
C7 C2 C3 118.4(2) ?
C7 C2 C1 119.4(3) ?
C3 C2 C1 122.2(3) ?
C4 C3 C2 120.6(3) ?
C4 C3 H3 119.7 ?
C2 C3 H3 119.7 ?
C5 C4 C3 119.5(3) ?
C5 C4 H4 120.3 ?
C3 C4 H4 120.3 ?
C6 C5 C4 121.3(3) ?
C6 C5 Cl1 119.6(2) ?
C4 C5 Cl1 119.1(2) ?
C5 C6 C7 118.8(3) ?
C5 C6 H6 120.6 ?
C7 C6 H6 120.6 ?
C6 C7 C2 121.3(3) ?
C6 C7 H7 119.3 ?
C2 C7 H7 119.3 ?
N2 C8 C14 124.5(3) y
N2 C8 H8 117.8 ?
C14 C8 H8 117.8 ?
C10 C9 C14 121.1(3) ?
C10 C9 H9 119.5 ?
C14 C9 H9 119.5 ?
C9 C10 C11 119.3(3) ?
C9 C10 H10 120.4 ?
C11 C10 H10 120.4 ?
C12 C11 C10 121.2(3) ?
C12 C11 Cl2 119.0(2) ?
C10 C11 Cl2 119.8(3) ?
C11 C12 C13 119.3(3) ?
C11 C12 H12 120.4 ?
C13 C12 H12 120.4 ?
C12 C13 C14 121.0(3) ?
C12 C13 H13 119.5 ?
C14 C13 H13 119.5 ?
C9 C14 C13 118.2(3) ?
C9 C14 C8 122.3(2) ?
C13 C14 C8 119.4(3) ?
N1 C15 C16 110.4(2) y
N1 C15 C17 108.3(2) ?
C16 C15 C17 110.2(2) ?
N1 C15 H15 109.3 ?
C16 C15 H15 109.3 ?
C17 C15 H15 109.3 ?
N2 C16 C15 112.3(2) y
N2 C16 H16A 109.1 ?
C15 C16 H16A 109.1 ?
N2 C16 H16B 109.1 ?
C15 C16 H16B 109.1 ?
H16A C16 H16B 107.9 ?
C15 C17 H17A 109.5 ?
C15 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C15 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C5 1.740(3) y
Cl2 C11 1.734(3) y
N1 C1 1.258(3) y
N1 C15 1.467(3) y
N2 C8 1.256(3) y
N2 C16 1.459(3) y
C1 C2 1.473(4) ?
C1 H1 0.9300 ?
C2 C7 1.383(4) ?
C2 C3 1.384(4) ?
C3 C4 1.382(4) ?
C3 H3 0.9300 ?
C4 C5 1.370(4) ?
C4 H4 0.9300 ?
C5 C6 1.369(4) ?
C6 C7 1.383(4) ?
C6 H6 0.9300 ?
C7 H7 0.9300 ?
C8 C14 1.463(4) ?
C8 H8 0.9300 ?
C9 C10 1.373(4) ?
C9 C14 1.378(4) ?
C9 H9 0.9300 ?
C10 C11 1.380(4) ?
C10 H10 0.9300 ?
C11 C12 1.361(4) ?
C12 C13 1.375(4) ?
C12 H12 0.9300 ?
C13 C14 1.394(3) ?
C13 H13 0.9300 ?
C15 C16 1.503(3) ?
C15 C17 1.523(4) ?
C15 H15 0.9800 ?
C16 H16A 0.9700 ?
C16 H16B 0.9700 ?
C17 H17A 0.9600 ?
C17 H17B 0.9600 ?
C17 H17C 0.9600 ?
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
C12 H12 N1 2_667 0.93 2.72 3.613(4) 161.1
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
C15 N1 C1 C2 -177.2(2) y
N1 C1 C2 C7 -173.8(3) ?
N1 C1 C2 C3 7.1(4) ?
C7 C2 C3 C4 1.0(4) ?
C1 C2 C3 C4 -179.8(2) ?
C2 C3 C4 C5 1.2(4) ?
C3 C4 C5 C6 -2.4(4) ?
C3 C4 C5 Cl1 179.4(2) ?
C4 C5 C6 C7 1.2(4) ?
Cl1 C5 C6 C7 179.4(2) ?
C5 C6 C7 C2 1.1(4) ?
C3 C2 C7 C6 -2.2(4) ?
C1 C2 C7 C6 178.6(2) ?
C16 N2 C8 C14 -178.2(2) y
C14 C9 C10 C11 -0.4(4) ?
C9 C10 C11 C12 -0.1(4) ?
C9 C10 C11 Cl2 180.0(2) ?
C10 C11 C12 C13 0.3(4) ?
Cl2 C11 C12 C13 -179.8(2) ?
C11 C12 C13 C14 0.1(4) ?
C10 C9 C14 C13 0.8(4) ?
C10 C9 C14 C8 -179.2(2) ?
C12 C13 C14 C9 -0.6(4) ?
C12 C13 C14 C8 179.3(2) ?
N2 C8 C14 C9 5.3(4) ?
N2 C8 C14 C13 -174.7(2) ?
C1 N1 C15 C16 -126.3(3) y
C1 N1 C15 C17 112.9(3) ?
C8 N2 C16 C15 -151.0(2) y
N1 C15 C16 N2 68.0(3) y
C17 C15 C16 N2 -172.4(2) ?
