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#$Date: 2025-07-01 14:16:55 +0300 (Tue, 01 Jul 2025) $
#$Revision: 1211 $
#$URL: svn://crystallography.net/testcod/cif/7/20/00/7200071.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_7200071
loop_
_publ_author_name
'Sanphui, Palash'
'Bolla, Geetha'
'Das, Uday'
'Mukherjee, Alok K.'
'Nangia, Ashwini'
_publ_section_title
;
 Acemetacin polymorphs: a rare case of carboxylic acid catemer and dimer
 synthons
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              34
_journal_paper_doi               10.1039/c2ce26534f
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C21 H18 Cl N O6'
_chemical_formula_weight         415.81
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 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                 102.47(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.858(3)
_cell_length_b                   4.8452(9)
_cell_length_c                   16.785(3)
_cell_measurement_reflns_used    557
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.3116
_cell_measurement_theta_min      3.3348
_cell_volume                     941.6(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω 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  0.0630
_diffrn_reflns_av_sigmaI/netI    0.1925
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3561
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.34
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         2846
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1903
_refine_ls_R_factor_gt           0.0882
_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)+(0.0292P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1598
_reflns_number_gt                1298
_reflns_number_total             2846
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26534f.txt
_cod_data_source_block           ACM_formI
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7200071
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.2432(2) 1.1007(7) -0.05933(17) 0.0801(11) Uani 1 1 d . . .
O6 O 0.3540(5) 0.0842(14) 0.5459(3) 0.0448(17) Uani 1 1 d . . .
O3 O 0.5624(5) 0.8330(12) 0.2575(3) 0.0351(16) Uani 1 1 d . . .
C11 C 0.2669(8) 0.5989(19) 0.3886(5) 0.031(2) Uani 1 1 d . . .
O2 O 0.4145(6) 0.5418(15) 0.2272(4) 0.059(2) Uani 1 1 d . . .
C12 C 0.1464(8) 0.5799(19) 0.3759(5) 0.033(2) Uani 1 1 d . . .
C14 C 0.1606(8) 0.2369(17) 0.4768(5) 0.038(2) Uani 1 1 d . . .
H14 H 0.1259 0.1178 0.5077 0.045 Uiso 1 1 calc R . .
O5 O 0.5791(6) 0.6420(14) 0.0541(4) 0.055(2) Uani 1 1 d . . .
O1 O -0.0849(6) 0.7507(17) 0.3258(4) 0.079(3) Uani 1 1 d . . .
C17 C 0.3018(8) -0.100(2) 0.5945(5) 0.051(3) Uani 1 1 d . . .
H17A H 0.2521 0.0028 0.6218 0.077 Uiso 1 1 calc R . .
H17B H 0.3610 -0.1891 0.6342 0.077 Uiso 1 1 calc R . .
H17C H 0.2573 -0.2367 0.5599 0.077 Uiso 1 1 calc R . .
C2 C -0.2006(8) 1.1759(19) 0.1034(7) 0.050(3) Uani 1 1 d . . .
H2 H -0.2560 1.3149 0.0937 0.059 Uiso 1 1 calc R . .
C15 C 0.2819(8) 0.2448(17) 0.4899(5) 0.032(2) Uani 1 1 d . . .
C13 C 0.0930(8) 0.4002(19) 0.4195(5) 0.042(3) Uani 1 1 d . . .
H13 H 0.0129 0.3904 0.4102 0.050 Uiso 1 1 calc R . .
O4 O 0.5066(8) 1.0092(16) 0.1054(5) 0.053(2) Uani 1 1 d . . .
C21 C 0.5596(8) 0.775(2) 0.1094(6) 0.036(2) Uani 1 1 d . . .
C6 C -0.0885(9) 0.830(2) 0.0535(6) 0.045(3) Uani 1 1 d . . .
H6 H -0.0702 0.7329 0.0101 0.054 Uiso 1 1 calc R . .
N1 N 0.0999(6) 0.7684(15) 0.3106(4) 0.0350(19) Uani 1 1 d . . .
C18 C 0.4124(7) 0.8900(19) 0.3278(5) 0.038(3) Uani 1 1 d . . .
H18A H 0.4113 1.0852 0.3148 0.046 Uiso 1 1 calc R . .
H18B H 0.4639 0.8644 0.3807 0.046 Uiso 1 1 calc R . .
C16 C 0.3342(8) 0.4256(16) 0.4459(5) 0.031(2) Uani 1 1 d . . .
H16 H 0.4143 0.4318 0.4544 0.037 Uiso 1 1 calc R . .
C4 C -0.0632(8) 0.9063(19) 0.1985(6) 0.038(3) Uani 1 1 d . . .
C20 C 0.6117(8) 0.6915(18) 0.1981(5) 0.041(3) Uani 1 1 d . . .
H20A H 0.6012 0.4945 0.2037 0.050 Uiso 1 1 calc R . .
H20B H 0.6941 0.7275 0.2095 0.050 Uiso 1 1 calc R . .
C19 C 0.4576(8) 0.7347(19) 0.2658(5) 0.032(2) Uani 1 1 d . . .
C3 C -0.1463(8) 1.102(2) 0.1823(6) 0.043(3) Uani 1 1 d . . .
H3 H -0.1680 1.1902 0.2258 0.052 Uiso 1 1 calc R . .
C7 C -0.0149(9) 0.804(2) 0.2847(6) 0.045(3) Uani 1 1 d . . .
C9 C 0.1812(7) 1.119(2) 0.2246(5) 0.045(3) Uani 1 1 d . . .
H9A H 0.2527 1.2184 0.2305 0.068 Uiso 1 1 calc R . .
H9B H 0.1211 1.2440 0.2313 0.068 Uiso 1 1 calc R . .
H9C H 0.1617 1.0375 0.1713 0.068 Uiso 1 1 calc R . .
C10 C 0.2943(7) 0.8017(17) 0.3329(5) 0.027(2) Uani 1 1 d . . .
C1 C -0.1692(8) 1.034(2) 0.0393(6) 0.050(3) Uani 1 1 d . . .
C8 C 0.1940(8) 0.8996(18) 0.2873(5) 0.031(2) Uani 1 1 d . . .
C5 C -0.0331(8) 0.765(2) 0.1340(6) 0.047(3) Uani 1 1 d . . .
H5 H 0.0235 0.6291 0.1442 0.057 Uiso 1 1 calc R . .
H4 H 0.469(13) 1.07(4) 0.066(8) 0.18(8) 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
_geom_angle_publ_flag
C15 O6 C17 117.5(7) . . ?
C19 O3 C20 114.9(7) . . ?
C16 C11 C12 118.7(9) . . ?
C16 C11 C10 133.2(8) . . ?
C12 C11 C10 108.1(8) . . ?
C13 C12 C11 122.1(9) . . ?
C13 C12 N1 131.3(8) . . ?
C11 C12 N1 106.5(8) . . ?
C13 C14 C15 121.3(9) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
O6 C17 H17A 109.5 . . ?
O6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C3 C2 C1 117.6(9) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
O6 C15 C16 116.3(8) . . ?
O6 C15 C14 123.9(8) . . ?
C16 C15 C14 119.8(8) . . ?
C14 C13 C12 118.3(9) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C21 O4 H4 123(10) . . ?
O5 C21 O4 127.4(9) . . ?
O5 C21 C20 120.4(10) . . ?
O4 C21 C20 111.8(9) . . ?
C1 C6 C5 119.6(9) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C7 N1 C8 131.1(8) . . ?
C7 N1 C12 121.4(8) . . ?
C8 N1 C12 107.5(7) . . ?
C19 C18 C10 112.6(8) . . ?
C19 C18 H18A 109.1 . . ?
C10 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C10 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C15 C16 C11 119.8(8) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
C3 C4 C5 119.2(9) . . ?
C3 C4 C7 121.9(9) . . ?
C5 C4 C7 118.3(9) . . ?
O3 C20 C21 114.1(7) . . ?
O3 C20 H20A 108.7 . . ?
C21 C20 H20A 108.7 . . ?
O3 C20 H20B 108.7 . . ?
C21 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
O2 C19 O3 120.8(9) . . ?
O2 C19 C18 127.4(9) . . ?
O3 C19 C18 111.8(8) . . ?
C4 C3 C2 122.7(9) . . ?
C4 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
O1 C7 N1 123.7(9) . . ?
O1 C7 C4 116.6(10) . . ?
N1 C7 C4 119.7(9) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 C11 108.2(8) . . ?
C8 C10 C18 126.3(8) . . ?
C11 C10 C18 125.5(8) . . ?
C6 C1 C2 121.2(9) . . ?
C6 C1 Cl1 119.7(9) . . ?
C2 C1 Cl1 118.9(8) . . ?
C10 C8 N1 109.7(8) . . ?
C10 C8 C9 126.6(8) . . ?
N1 C8 C9 123.7(8) . . ?
C4 C5 C6 119.7(9) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.728(10) . ?
O6 C15 1.368(9) . ?
O6 C17 1.437(9) . ?
O3 C19 1.366(10) . ?
O3 C20 1.435(9) . ?
C11 C16 1.391(11) . ?
C11 C12 1.402(11) . ?
C11 C10 1.441(11) . ?
O2 C19 1.188(10) . ?
C12 C13 1.377(11) . ?
C12 N1 1.442(10) . ?
C14 C13 1.364(11) . ?
C14 C15 1.407(11) . ?
C14 H14 0.9300 . ?
O5 C21 1.193(10) . ?
O1 C7 1.216(11) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C2 C3 1.390(12) . ?
C2 C1 1.393(12) . ?
C2 H2 0.9300 . ?
C15 C16 1.377(11) . ?
C13 H13 0.9300 . ?
O4 C21 1.292(12) . ?
O4 H4 0.77(14) . ?
C21 C20 1.537(11) . ?
C6 C1 1.364(13) . ?
C6 C5 1.405(12) . ?
C6 H6 0.9300 . ?
N1 C7 1.348(11) . ?
N1 C8 1.411(10) . ?
C18 C19 1.476(11) . ?
C18 C10 1.484(11) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C16 H16 0.9300 . ?
C4 C3 1.351(11) . ?
C4 C5 1.390(11) . ?
C4 C7 1.520(12) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C3 H3 0.9300 . ?
C9 C8 1.481(11) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C8 1.353(11) . ?
C5 H5 0.9300 . ?
