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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/75/4507584.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_4507584
loop_
_publ_author_name
'Goud, N. Rajesh'
'Suresh, Kuthuru'
'Nangia, Ashwini'
_publ_section_title
;
 Solubility and Stability Advantage of Aceclofenac Salts
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1590
_journal_paper_doi               10.1021/cg301825u
_journal_volume                  13
_journal_year                    2013
_chemical_formula_sum            'C18 H18 Cl2 N2 O4'
_chemical_formula_weight         397.24
_chemical_name_systematic
; 
Aceclofenac-piperazine(0.5)
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.038(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1898(11)
_cell_length_b                   5.5983(7)
_cell_length_c                   34.890(4)
_cell_measurement_reflns_used    3282
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.95
_cell_measurement_theta_min      2.34
_cell_volume                     1790.5(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0605
_diffrn_reflns_av_sigmaI/netI    0.0453
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            17574
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         1.17
_exptl_absorpt_coefficient_mu    0.389
_exptl_absorpt_correction_T_max  0.9123
_exptl_absorpt_correction_T_min  0.8351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3515
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0499
_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)+(0.0428P)²+1.3416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1112
_reflns_number_gt                3143
_reflns_number_total             3515
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301825u_si_003.cif
_cod_data_source_block           Aceclofenac-piperazine
_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 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               4507584
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.64887(6) 0.62742(11) 0.134206(17) 0.02140(17) Uani 1 1 d .
Cl2 Cl 0.34800(7) 0.15992(11) 0.238842(17) 0.02221(17) Uani 1 1 d .
O3 O 0.48976(17) 0.1185(3) 0.08169(5) 0.0172(4) Uani 1 1 d .
O1 O 0.67499(19) -0.2146(3) 0.05501(5) 0.0244(4) Uani 1 1 d .
O2 O 0.82261(17) 0.0733(3) 0.03733(5) 0.0168(4) Uani 1 1 d .
N1 N 0.4286(2) 0.2711(4) 0.15909(6) 0.0174(4) Uani 1 1 d .
O4 O 0.34235(19) -0.1069(3) 0.04226(5) 0.0264(4) Uani 1 1 d .
C1 C 0.7026(2) -0.0013(4) 0.04780(6) 0.0138(5) Uani 1 1 d .
C11 C 0.4936(2) 0.4152(4) 0.18812(7) 0.0172(5) Uani 1 1 d .
C3 C 0.3795(2) -0.0373(4) 0.07378(7) 0.0158(5) Uani 1 1 d .
C16 C 0.4622(3) 0.3902(4) 0.22663(7) 0.0188(5) Uani 1 1 d .
C5 C 0.2153(2) 0.0898(4) 0.12574(6) 0.0145(5) Uani 1 1 d .
C7 C -0.0250(3) 0.2540(5) 0.13283(7) 0.0210(5) Uani 1 1 d .
H7 H -0.1275 0.2479 0.1270 0.025 Uiso 1 1 calc R
C8 C 0.0353(3) 0.4303(5) 0.15669(7) 0.0201(5) Uani 1 1 d .
H8 H -0.0260 0.5458 0.1673 0.024 Uiso 1 1 calc R
C4 C 0.3091(3) -0.1056(4) 0.11021(7) 0.0165(5) Uani 1 1 d .
H4A H 0.3866 -0.1483 0.1302 0.020 Uiso 1 1 calc R
H4B H 0.2480 -0.2492 0.1050 0.020 Uiso 1 1 calc R
C2 C 0.5803(3) 0.1805(4) 0.05075(7) 0.0175(5) Uani 1 1 d .
H2A H 0.6227 0.3413 0.0555 0.021 Uiso 1 1 calc R
H2B H 0.5195 0.1855 0.0262 0.021 Uiso 1 1 calc R
C6 C 0.0650(3) 0.0861(4) 0.11745(7) 0.0186(5) Uani 1 1 d .
H6 H 0.0233 -0.0341 0.1009 0.022 Uiso 1 1 calc R
C15 C 0.5216(3) 0.5378(5) 0.25524(7) 0.0220(6) Uani 1 1 d .
H15 H 0.4948 0.5198 0.2809 0.026 Uiso 1 1 calc R
C9 C 0.1850(3) 0.4393(4) 0.16522(7) 0.0170(5) Uani 1 1 d .
H9 H 0.2256 0.5622 0.1814 0.020 Uiso 1 1 calc R
C12 C 0.5982(2) 0.5899(4) 0.18093(7) 0.0181(5) Uani 1 1 d .
C13 C 0.6607(3) 0.7349(5) 0.20945(8) 0.0232(6) Uani 1 1 d .
H13 H 0.7314 0.8505 0.2035 0.028 Uiso 1 1 calc R
C10 C 0.2765(3) 0.2689(4) 0.15013(6) 0.0162(5) Uani 1 1 d .
C14 C 0.6204(3) 0.7121(5) 0.24647(8) 0.0251(6) Uani 1 1 d .
H14 H 0.6604 0.8160 0.2660 0.030 Uiso 1 1 calc R
N2 N 0.8794(2) 0.5281(4) 0.02304(6) 0.0185(5) Uani 1 1 d .
C17 C 0.8636(3) 0.5800(4) -0.01862(7) 0.0196(5) Uani 1 1 d .
H17A H 0.8832 0.7514 -0.0230 0.023 Uiso 1 1 calc R
H17B H 0.7625 0.5451 -0.0288 0.023 Uiso 1 1 calc R
C18 C 1.0306(3) 0.5711(4) 0.03935(7) 0.0189(5) Uani 1 1 d .
H18A H 1.0381 0.5306 0.0670 0.023 Uiso 1 1 calc R
H18B H 1.0554 0.7421 0.0367 0.023 Uiso 1 1 calc R
H1B H 0.480(3) 0.244(5) 0.1409(8) 0.021(7) Uiso 1 1 d .
H1A H 0.815(3) 0.629(5) 0.0367(8) 0.027(8) Uiso 1 1 d .
H2C H 0.855(3) 0.379(6) 0.0263(9) 0.036(9) Uiso 1 1 d .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C3 O3 C2 117.61(18) . .
C11 N1 C10 122.1(2) . .
C11 N1 H1B 115.1(19) . .
C10 N1 H1B 115.8(19) . .
O1 C1 O2 124.8(2) . .
O1 C1 C2 117.5(2) . .
O2 C1 C2 117.6(2) . .
N1 C11 C16 122.1(2) . .
N1 C11 C12 122.4(2) . .
C16 C11 C12 115.5(2) . .
O4 C3 O3 124.1(2) . .
O4 C3 C4 125.4(2) . .
O3 C3 C4 110.5(2) . .
C15 C16 C11 122.4(2) . .
C15 C16 Cl2 118.9(2) . .
C11 C16 Cl2 118.63(19) . .
C6 C5 C10 119.0(2) . .
C6 C5 C4 119.7(2) . .
C10 C5 C4 121.2(2) . .
C8 C7 C6 119.6(2) . .
C8 C7 H7 120.2 . .
C6 C7 H7 120.2 . .
C7 C8 C9 120.3(2) . .
C7 C8 H8 119.9 . .
C9 C8 H8 119.9 . .
C3 C4 C5 113.87(19) . .
C3 C4 H4A 108.8 . .
C5 C4 H4A 108.8 . .
C3 C4 H4B 108.8 . .
C5 C4 H4B 108.8 . .
H4A C4 H4B 107.7 . .
O3 C2 C1 110.77(18) . .
O3 C2 H2A 109.5 . .
C1 C2 H2A 109.5 . .
O3 C2 H2B 109.5 . .
C1 C2 H2B 109.5 . .
H2A C2 H2B 108.1 . .
C7 C6 C5 121.4(2) . .
C7 C6 H6 119.3 . .
C5 C6 H6 119.3 . .
C16 C15 C14 119.8(2) . .
C16 C15 H15 120.1 . .
C14 C15 H15 120.1 . .
C8 C9 C10 120.5(2) . .
C8 C9 H9 119.7 . .
C10 C9 H9 119.7 . .
C13 C12 C11 122.4(2) . .
C13 C12 Cl1 118.72(19) . .
C11 C12 Cl1 118.85(19) . .
C14 C13 C12 119.9(2) . .
C14 C13 H13 120.1 . .
C12 C13 H13 120.1 . .
C9 C10 C5 119.3(2) . .
C9 C10 N1 121.6(2) . .
C5 C10 N1 119.2(2) . .
C13 C14 C15 119.9(2) . .
C13 C14 H14 120.1 . .
C15 C14 H14 120.1 . .
C17 N2 C18 111.70(19) . .
C17 N2 H1A 110.3(16) . .
C18 N2 H1A 107.9(17) . .
C17 N2 H2C 108(2) . .
C18 N2 H2C 110(2) . .
H1A N2 H2C 109(3) . .
N2 C17 C18 109.8(2) . 3_765
N2 C17 H17A 109.7 . .
C18 C17 H17A 109.7 3_765 .
N2 C17 H17B 109.7 . .
C18 C17 H17B 109.7 3_765 .
H17A C17 H17B 108.2 . .
N2 C18 C17 110.0(2) . 3_765
N2 C18 H18A 109.7 . .
C17 C18 H18A 109.7 3_765 .
N2 C18 H18B 109.7 . .
C17 C18 H18B 109.7 3_765 .
H18A C18 H18B 108.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C12 1.739(2) .
Cl2 C16 1.734(3) .
O3 C3 1.350(3) .
O3 C2 1.450(3) .
O1 C1 1.250(3) .
O2 C1 1.257(3) .
N1 C11 1.396(3) .
N1 C10 1.411(3) .
N1 H1B 0.83(3) .
O4 C3 1.194(3) .
C1 C2 1.526(3) .
C11 C16 1.401(3) .
C11 C12 1.406(3) .
C3 C4 1.516(3) .
C16 C15 1.379(4) .
C5 C6 1.391(3) .
C5 C10 1.406(3) .
C5 C4 1.516(3) .
C7 C8 1.382(4) .
C7 C6 1.385(3) .
C7 H7 0.9500 .
C8 C9 1.388(3) .
C8 H8 0.9500 .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C6 H6 0.9500 .
C15 C14 1.381(4) .
C15 H15 0.9500 .
C9 C10 1.399(3) .
C9 H9 0.9500 .
C12 C13 1.378(4) .
C13 C14 1.375(4) .
C13 H13 0.9500 .
C14 H14 0.9500 .
N2 C17 1.479(3) .
N2 C18 1.484(3) .
N2 H1A 0.97(3) .
N2 H2C 0.88(3) .
C17 C18 1.511(3) 3_765
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C17 1.511(3) 3_765
C18 H18A 0.9900 .
C18 H18B 0.9900 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146448
