#------------------------------------------------------------------------------
#$Date: 2025-08-19 14:52:15 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301804 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/50/2215006.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_2215006
loop_
_publ_author_name
'Jin, Hui-Min'
'Li, Pei-Fan'
'Li, Cai-Yun'
'Liu, Bin'
_publ_section_title
;
 1,4-Bis(4-chlorobenzoyl)piperazine
;
_journal_coeditor_code           BT2456
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3689
_journal_page_last               o3689
_journal_paper_doi               10.1107/S1600536807037300
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C18 H16 Cl2 N2 O2'
_chemical_formula_moiety         'C18 H16 Cl2 N2 O2'
_chemical_formula_sum            'C18 H16 Cl2 N2 O2'
_chemical_formula_weight         363.23
_chemical_name_systematic
;
1,4-Bis(4-chlorobenzoyl)piperazine
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 96.959(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.892(2)
_cell_length_b                   11.413(2)
_cell_length_c                   12.653(2)
_cell_measurement_reflns_used    1786
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.15
_cell_measurement_theta_min      2.51
_cell_volume                     1704.7(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART 1K 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  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9538
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.394
_exptl_absorpt_correction_T_max  0.9543
_exptl_absorpt_correction_T_min  0.9397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.215
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0605P)²+0.0445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1320
_reflns_number_gt                1795
_reflns_number_total             3473
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2456.cif
_cod_data_source_block           I
_cod_original_cell_volume        1704.6(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2215006
_cod_database_fobs_code          2215006
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
'-x+1/2, y+1/2, -z+1/2'
'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
Cl Cl1 0.07297(8) 1.14374(6) 0.33438(7) 0.0734(3) Uani d . 1
Cl Cl2 0.67186(8) 1.15311(6) 0.41373(7) 0.0755(3) Uani d . 1
O O1 0.10101(17) 0.56724(16) 0.25514(15) 0.0608(6) Uani d . 1
O O2 0.73471(16) 0.58451(15) 0.37660(16) 0.0604(6) Uani d . 1
N N1 0.05304(18) 0.55966(16) 0.42159(16) 0.0431(6) Uani d . 1
N N2 0.56644(18) 0.56438(18) 0.43733(19) 0.0517(6) Uani d . 1
C C1 0.1649(2) 0.8111(2) 0.30465(19) 0.0445(6) Uani d . 1
H H1 0.2263 0.7707 0.2835 0.053 Uiso calc R 1
C C2 0.1644(2) 0.9320(2) 0.3036(2) 0.0485(7) Uani d . 1
H H2 0.2255 0.9731 0.2825 0.058 Uiso calc R 1
C C3 0.0730(2) 0.9914(2) 0.3340(2) 0.0466(7) Uani d . 1
C C4 -0.0192(2) 0.9316(2) 0.3633(2) 0.0524(7) Uani d . 1
H H4 -0.0816 0.9725 0.3819 0.063 Uiso calc R 1
C C5 -0.0182(2) 0.8109(2) 0.3649(2) 0.0462(7) Uani d . 1
H H5 -0.0803 0.7705 0.3848 0.055 Uiso calc R 1
C C6 0.0741(2) 0.7489(2) 0.33721(18) 0.0393(6) Uani d . 1
C C7 0.0774(2) 0.6181(2) 0.3351(2) 0.0407(6) Uani d . 1
C C8 0.0563(2) 0.6076(2) 0.52951(19) 0.0446(7) Uani d . 1
H H8A 0.0580 0.6925 0.5264 0.054 Uiso calc R 1
H H8B 0.1248 0.5815 0.5725 0.054 Uiso calc R 1
C C9 0.0460(2) 0.4316(2) 0.4195(2) 0.0459(7) Uani d . 1
H H9A 0.1142 0.3984 0.4578 0.055 Uiso calc R 1
H H9B 0.0398 0.4041 0.3464 0.055 Uiso calc R 1
C C10 0.6690(2) 0.8217(2) 0.31981(19) 0.0444(7) Uani d . 1
H H10 0.6819 0.7807 0.2589 0.053 Uiso calc R 1
C C11 0.6757(2) 0.9420(2) 0.3207(2) 0.0463(7) Uani d . 1
H H11 0.6916 0.9825 0.2604 0.056 Uiso calc R 1
C C12 0.6586(2) 1.0017(2) 0.4119(2) 0.0443(6) Uani d . 1
C C13 0.6332(2) 0.9435(2) 0.5015(2) 0.0468(7) Uani d . 1
H H13 0.6215 0.9849 0.5625 0.056 Uiso calc R 1
C C14 0.6253(2) 0.8229(2) 0.4990(2) 0.0450(7) Uani d . 1
H H14 0.6077 0.7830 0.5589 0.054 Uiso calc R 1
C C15 0.64333(19) 0.7606(2) 0.40892(19) 0.0386(6) Uani d . 1
C C16 0.6512(2) 0.6301(2) 0.4060(2) 0.0423(7) Uani d . 1
C C17 0.4532(2) 0.6053(2) 0.4531(2) 0.0516(7) Uani d . 1
H H17A 0.3984 0.5761 0.3962 0.062 Uiso calc R 1
H H17B 0.4512 0.6902 0.4510 0.062 Uiso calc R 1
C C18 0.5771(2) 0.4364(2) 0.4426(2) 0.0574(8) Uani d . 1
H H18A 0.6542 0.4136 0.4347 0.069 Uiso calc R 1
H H18B 0.5270 0.4009 0.3852 0.069 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'
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
C7 N1 C9 . . 119.9(2)
C7 N1 C8 . . 126.1(2)
C9 N1 C8 . . 112.61(19)
C16 N2 C17 . . 126.4(2)
C16 N2 C18 . . 120.1(2)
C17 N2 C18 . . 112.8(2)
C2 C1 C6 . . 120.6(2)
C2 C1 H1 . . 119.7
C6 C1 H1 . . 119.7
C3 C2 C1 . . 119.5(2)
C3 C2 H2 . . 120.3
C1 C2 H2 . . 120.2
C2 C3 C4 . . 120.9(2)
C2 C3 Cl1 . . 119.6(2)
C4 C3 Cl1 . . 119.5(2)
C5 C4 C3 . . 119.5(3)
C5 C4 H4 . . 120.3
C3 C4 H4 . . 120.3
C4 C5 C6 . . 120.8(2)
C4 C5 H5 . . 119.6
C6 C5 H5 . . 119.6
C5 C6 C1 . . 118.7(2)
C5 C6 C7 . . 122.5(2)
C1 C6 C7 . . 118.7(2)
O1 C7 N1 . . 122.0(2)
O1 C7 C6 . . 119.8(2)
N1 C7 C6 . . 118.2(2)
N1 C8 C9 . 2_566 110.8(2)
N1 C8 H8A . . 109.5
C9 C8 H8A 2_566 . 109.5
N1 C8 H8B . . 109.5
C9 C8 H8B 2_566 . 109.5
H8A C8 H8B . . 108.1
N1 C9 C8 . 2_566 109.5(2)
N1 C9 H9A . . 109.8
C8 C9 H9A 2_566 . 109.8
N1 C9 H9B . . 109.8
C8 C9 H9B 2_566 . 109.8
H9A C9 H9B . . 108.2
C11 C10 C15 . . 120.8(2)
C11 C10 H10 . . 119.6
C15 C10 H10 . . 119.6
C10 C11 C12 . . 119.1(2)
C10 C11 H11 . . 120.5
C12 C11 H11 . . 120.5
C11 C12 C13 . . 121.4(2)
C11 C12 Cl2 . . 118.8(2)
C13 C12 Cl2 . . 119.8(2)
C12 C13 C14 . . 118.9(2)
C12 C13 H13 . . 120.6
C14 C13 H13 . . 120.6
C13 C14 C15 . . 121.0(2)
C13 C14 H14 . . 119.5
C15 C14 H14 . . 119.5
C14 C15 C10 . . 118.8(2)
C14 C15 C16 . . 123.4(2)
C10 C15 C16 . . 117.4(2)
O2 C16 N2 . . 121.1(2)
O2 C16 C15 . . 119.3(2)
N2 C16 C15 . . 119.6(2)
N2 C17 C18 . 2_666 110.2(2)
N2 C17 H17A . . 109.6
C18 C17 H17A 2_666 . 109.6
N2 C17 H17B . . 109.6
C18 C17 H17B 2_666 . 109.6
H17A C17 H17B . . 108.1
N2 C18 C17 . 2_666 109.3(2)
N2 C18 H18A . . 109.8
C17 C18 H18A 2_666 . 109.8
N2 C18 H18B . . 109.8
C17 C18 H18B 2_666 . 109.8
H18A C18 H18B . . 108.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cl1 C3 . 1.739(3)
Cl2 C12 . 1.735(3)
O1 C7 . 1.228(3)
O2 C16 . 1.219(3)
N1 C7 . 1.343(3)
N1 C9 . 1.464(3)
N1 C8 . 1.467(3)
N2 C16 . 1.354(3)
N2 C17 . 1.461(3)
N2 C18 . 1.467(3)
C1 C2 . 1.380(3)
C1 C6 . 1.395(3)
C1 H1 . 0.9300
C2 C3 . 1.375(4)
C2 H2 . 0.9300
C3 C4 . 1.380(4)
C4 C5 . 1.378(3)
C4 H4 . 0.9300
C5 C6 . 1.387(3)
C5 H5 . 0.9300
C6 C7 . 1.494(3)
C8 C9 2_566 1.513(3)
C8 H8A . 0.9700
C8 H8B . 0.9700
C9 C8 2_566 1.513(3)
C9 H9A . 0.9700
C9 H9B . 0.9700
C10 C11 . 1.376(3)
C10 C15 . 1.391(3)
C10 H10 . 0.9300
C11 C12 . 1.377(3)
C11 H11 . 0.9300
C12 C13 . 1.378(3)
C13 C14 . 1.380(3)
C13 H13 . 0.9300
C14 C15 . 1.382(3)
C14 H14 . 0.9300
C15 C16 . 1.492(3)
C17 C18 2_666 1.488(4)
C17 H17A . 0.9700
C17 H17B . 0.9700
C18 C17 2_666 1.488(4)
C18 H18A . 0.9700
C18 H18B . 0.9700
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
C2 H2 O1 3_555 0.93 2.42 3.350(3) 173
C11 H11 O2 3_655 0.93 2.34 3.265(3) 170
C18 H18B Cg1 ? 0.97 Missing 3.812(3) 155
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_4
_geom_torsion
C6 C1 C2 C3 . -0.6(4)
C1 C2 C3 C4 . -1.4(4)
C1 C2 C3 Cl1 . 179.15(19)
C2 C3 C4 C5 . 1.7(4)
Cl1 C3 C4 C5 . -178.8(2)
C3 C4 C5 C6 . -0.1(4)
C4 C5 C6 C1 . -1.9(4)
C4 C5 C6 C7 . -178.3(2)
C2 C1 C6 C5 . 2.2(4)
C2 C1 C6 C7 . 178.8(2)
C9 N1 C7 O1 . -4.5(4)
C8 N1 C7 O1 . 160.9(3)
C9 N1 C7 C6 . 174.9(2)
C8 N1 C7 C6 . -19.6(4)
C5 C6 C7 O1 . 127.9(3)
C1 C6 C7 O1 . -48.6(3)
C5 C6 C7 N1 . -51.5(3)
C1 C6 C7 N1 . 132.0(2)
C7 N1 C8 C9 2_566 136.7(2)
C9 N1 C8 C9 2_566 -57.0(3)
C7 N1 C9 C8 2_566 -136.4(2)
C8 N1 C9 C8 2_566 56.2(3)
C15 C10 C11 C12 . 1.1(4)
C10 C11 C12 C13 . -1.0(4)
C10 C11 C12 Cl2 . 177.85(19)
C11 C12 C13 C14 . 0.2(4)
Cl2 C12 C13 C14 . -178.64(19)
C12 C13 C14 C15 . 0.5(4)
C13 C14 C15 C10 . -0.4(4)
C13 C14 C15 C16 . 171.6(2)
C11 C10 C15 C14 . -0.5(4)
C11 C10 C15 C16 . -172.9(2)
C17 N2 C16 O2 . -166.5(3)
C18 N2 C16 O2 . 3.8(4)
C17 N2 C16 C15 . 14.5(4)
C18 N2 C16 C15 . -175.3(2)
C14 C15 C16 O2 . -124.8(3)
C10 C15 C16 O2 . 47.3(3)
C14 C15 C16 N2 . 54.3(4)
C10 C15 C16 N2 . -133.6(3)
C16 N2 C17 C18 2_666 -131.6(3)
C18 N2 C17 C18 2_666 57.6(3)
C16 N2 C18 C17 2_666 131.4(3)
C17 N2 C18 C17 2_666 -57.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139072881
