#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/44/2224499.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_2224499
loop_
_publ_author_name
'Xu, Rui-Bo'
'Xu, Xing-You'
'Wang, Da-Qi'
'Yang, Xu-Jie'
'Li, Shuan'
_publ_section_title
;
 1,4-Bis{3-[4-(dimethylamino)benzylideneamino]propyl}piperazine
;
_journal_coeditor_code           XU2643
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2997
_journal_paper_doi               10.1107/S1600536809045619
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C28 H42 N6'
_chemical_formula_moiety         'C28 H42 N6'
_chemical_formula_sum            'C28 H42 N6'
_chemical_formula_weight         462.68
_chemical_name_systematic
;
1,4-Bis{3-[4-(dimethylamino)benzylideneamino]propyl}piperazine
;
_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                 105.921(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   17.599(2)
_cell_length_b                   6.4146(12)
_cell_length_c                   12.6643(18)
_cell_measurement_reflns_used    683
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      49.484
_cell_measurement_theta_min      2.407
_cell_volume                     1374.8(4)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 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  0.0883
_diffrn_reflns_av_sigmaI/netI    0.1111
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6788
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.41
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.118
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.172
_refine_ls_extinction_coef       0.015(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.337
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.337
_refine_ls_R_factor_all          0.1938
_refine_ls_R_factor_gt           0.0947
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0892P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2772
_refine_ls_wR_factor_ref         0.2982
_reflns_number_gt                961
_reflns_number_total             2416
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2643.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224499
_cod_database_fobs_code          2224499
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
N N1 0.9158(3) -0.7316(8) 1.1684(4) 0.0687(16) Uani d . 1 . .
N N2 0.7447(3) 0.0908(8) 0.9057(5) 0.0667(15) Uani d . 1 . .
N N3 0.5629(3) 0.4652(7) 0.5991(4) 0.0590(14) Uani d . 1 . .
C C1 0.7396(3) -0.0090(10) 0.9908(6) 0.0625(17) Uani d . 1 . .
H H1 0.7045 0.0408 1.0280 0.075 Uiso calc R 1 . .
C C2 0.7852(3) -0.1960(9) 1.0339(5) 0.0541(16) Uani d . 1 . .
C C3 0.8387(3) -0.2867(10) 0.9837(5) 0.0598(17) Uani d . 1 . .
H H3 0.8455 -0.2295 0.9194 0.072 Uiso calc R 1 . .
C C4 0.8822(3) -0.4629(9) 1.0298(5) 0.0563(16) Uani d . 1 . .
H H4 0.9183 -0.5194 0.9961 0.068 Uiso calc R 1 . .
C C5 0.8728(3) -0.5567(9) 1.1258(5) 0.0539(16) Uani d . 1 . .
C C6 0.8190(3) -0.4665(9) 1.1741(5) 0.0580(16) Uani d . 1 . .
H H6 0.8113 -0.5255 1.2375 0.070 Uiso calc R 1 . .
C C7 0.7766(3) -0.2905(10) 1.1299(5) 0.0672(18) Uani d . 1 . .
H H7 0.7414 -0.2333 1.1649 0.081 Uiso calc R 1 . .
C C8 0.9031(4) -0.8320(10) 1.2662(5) 0.083(2) Uani d . 1 . .
H H8A 0.9375 -0.9505 1.2856 0.124 Uiso calc R 1 . .
H H8B 0.8492 -0.8767 1.2510 0.124 Uiso calc R 1 . .
H H8C 0.9145 -0.7346 1.3260 0.124 Uiso calc R 1 . .
C C9 0.9638(4) -0.8399(10) 1.1115(6) 0.083(2) Uani d . 1 . .
H H9A 0.9889 -0.9563 1.1548 0.125 Uiso calc R 1 . .
H H9B 1.0033 -0.7471 1.0993 0.125 Uiso calc R 1 . .
H H9C 0.9312 -0.8890 1.0422 0.125 Uiso calc R 1 . .
C C10 0.6968(4) 0.2755(10) 0.8724(5) 0.0704(19) Uani d . 1 . .
H H10A 0.7309 0.3962 0.8784 0.084 Uiso calc R 1 . .
H H10B 0.6636 0.2962 0.9214 0.084 Uiso calc R 1 . .
C C11 0.6451(4) 0.2571(9) 0.7554(5) 0.0665(18) Uani d . 1 . .
H H11A 0.6095 0.1398 0.7500 0.080 Uiso calc R 1 . .
H H11B 0.6781 0.2311 0.7067 0.080 Uiso calc R 1 . .
C C12 0.5971(3) 0.4555(9) 0.7193(5) 0.0637(18) Uani d . 1 . .
H H12A 0.5548 0.4618 0.7547 0.076 Uiso calc R 1 . .
H H12B 0.6309 0.5758 0.7431 0.076 Uiso calc R 1 . .
C C13 0.5345(4) 0.6762(9) 0.5644(5) 0.0710(19) Uani d . 1 . .
H H13A 0.5778 0.7745 0.5873 0.085 Uiso calc R 1 . .
H H13B 0.4940 0.7152 0.5995 0.085 Uiso calc R 1 . .
C C14 0.5005(4) 0.6860(10) 0.4399(5) 0.0678(18) Uani d . 1 . .
H H14A 0.4803 0.8251 0.4189 0.081 Uiso calc R 1 . .
H H14B 0.5422 0.6586 0.4051 0.081 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'
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
C5 N1 C9 . . 122.3(5) ?
C5 N1 C8 . . 119.7(5) ?
C9 N1 C8 . . 117.3(5) ?
C1 N2 C10 . . 119.0(5) ?
C13 N3 C14 . 3_666 110.2(5) ?
C13 N3 C12 . . 110.9(5) ?
C14 N3 C12 3_666 . 112.2(5) ?
N2 C1 C2 . . 124.6(6) ?
N2 C1 H1 . . 117.7 ?
C2 C1 H1 . . 117.7 ?
C7 C2 C3 . . 117.4(6) ?
C7 C2 C1 . . 120.0(6) ?
C3 C2 C1 . . 122.7(6) ?
C4 C3 C2 . . 120.4(6) ?
C4 C3 H3 . . 119.8 ?
C2 C3 H3 . . 119.8 ?
C3 C4 C5 . . 121.7(6) ?
C3 C4 H4 . . 119.2 ?
C5 C4 H4 . . 119.2 ?
N1 C5 C6 . . 122.3(6) ?
N1 C5 C4 . . 120.3(6) ?
C6 C5 C4 . . 117.4(6) ?
C7 C6 C5 . . 121.3(6) ?
C7 C6 H6 . . 119.3 ?
C5 C6 H6 . . 119.3 ?
C6 C7 C2 . . 121.9(6) ?
C6 C7 H7 . . 119.1 ?
C2 C7 H7 . . 119.1 ?
N1 C8 H8A . . 109.5 ?
N1 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
N1 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N1 C9 H9A . . 109.5 ?
N1 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
N1 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
N2 C10 C11 . . 111.5(5) ?
N2 C10 H10A . . 109.3 ?
C11 C10 H10A . . 109.3 ?
N2 C10 H10B . . 109.3 ?
C11 C10 H10B . . 109.3 ?
H10A C10 H10B . . 108.0 ?
C10 C11 C12 . . 111.2(5) ?
C10 C11 H11A . . 109.4 ?
C12 C11 H11A . . 109.4 ?
C10 C11 H11B . . 109.4 ?
C12 C11 H11B . . 109.4 ?
H11A C11 H11B . . 108.0 ?
N3 C12 C11 . . 112.3(5) ?
N3 C12 H12A . . 109.1 ?
C11 C12 H12A . . 109.1 ?
N3 C12 H12B . . 109.1 ?
C11 C12 H12B . . 109.1 ?
H12A C12 H12B . . 107.9 ?
N3 C13 C14 . . 110.6(5) ?
N3 C13 H13A . . 109.5 ?
C14 C13 H13A . . 109.5 ?
N3 C13 H13B . . 109.5 ?
C14 C13 H13B . . 109.5 ?
H13A C13 H13B . . 108.1 ?
N3 C14 C13 3_666 . 111.6(5) ?
N3 C14 H14A 3_666 . 109.3 ?
C13 C14 H14A . . 109.3 ?
N3 C14 H14B 3_666 . 109.3 ?
C13 C14 H14B . . 109.3 ?
H14A C14 H14B . . 108.0 ?
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
N1 C5 . 1.378(7) ?
N1 C9 . 1.432(7) ?
N1 C8 . 1.466(7) ?
N2 C1 . 1.278(7) ?
N2 C10 . 1.448(7) ?
N3 C13 . 1.468(7) ?
N3 C14 3_666 1.459(7) ?
N3 C12 . 1.477(7) ?
C1 C2 . 1.462(8) ?
C1 H1 . 0.9300 ?
C2 C7 . 1.404(7) ?
C2 C3 . 1.400(7) ?
C3 C4 . 1.399(8) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.407(7) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.387(8) ?
C6 C7 . 1.384(8) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 C11 . 1.516(8) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.527(8) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.527(8) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 N3 3_666 1.459(7) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 324110
