#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/93/4509378.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4509378
loop_
_publ_author_name
'Martins, Felipe T.'
'Bocelli, Márcio D.'
'Bonfilio, Rudy'
'de Araújo, Magali B.'
'Lima, Patrícia V. de'
'Neves, Person P.'
'Veloso, Marcia P.'
'Ellena, Javier'
'Doriguetto, Antônio C.'
_publ_section_title
;
 Conformational Polymorphism in Racemic Crystals of the Diuretic Drug
 Chlortalidone
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3235
_journal_paper_doi               10.1021/cg801322x
_journal_volume                  9
_journal_year                    2009
_chemical_formula_sum            'C14 H11 Cl N2 O4 S'
_chemical_formula_weight         338.76
_chemical_name_common            'chlortalidone Form III'
_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           SHELXL-97
_cell_angle_alpha                80.448(2)
_cell_angle_beta                 79.277(2)
_cell_angle_gamma                86.106(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9957(2)
_cell_length_b                   8.1467(2)
_cell_length_c                   11.4761(3)
_cell_measurement_reflns_used    14365
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.68
_cell_measurement_theta_min      3.35
_cell_volume                     723.77(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_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  0.0730
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14365
_diffrn_reflns_theta_full        26.68
_diffrn_reflns_theta_max         26.68
_diffrn_reflns_theta_min         3.35
_exptl_absorpt_coefficient_mu    0.428
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.151
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0534
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0909P)²+0.1363P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1503
_reflns_number_gt                2455
_reflns_number_total             2961
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg801322xsup1.cif
_cod_data_source_block           CTDFormIII
_cod_database_code               4509378
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
S1 S 1.33457(7) 0.11903(7) 0.16438(5) 0.0477(2) Uani 1 1 d .
Cl1 Cl 1.19244(8) 0.14129(9) -0.08663(5) 0.0611(2) Uani 1 1 d .
O2 O 0.7773(2) 0.27596(18) 0.43828(15) 0.0476(4) Uani 1 1 d .
O3 O 1.3486(2) 0.1320(2) 0.28475(16) 0.0614(5) Uani 1 1 d .
O1 O 0.35055(19) 0.6092(2) 0.34298(16) 0.0536(4) Uani 1 1 d .
O4 O 1.4575(2) 0.1989(2) 0.06842(17) 0.0609(5) Uani 1 1 d .
C4 C 0.6303(3) 0.8267(3) 0.3862(2) 0.0485(5) Uani 1 1 d .
H4 H 0.5289 0.8903 0.3916 0.058 Uiso 1 1 calc R
C10 C 1.0241(3) 0.2628(3) 0.2408(2) 0.0419(5) Uani 1 1 d .
H10 H 1.0605 0.2519 0.3142 0.050 Uiso 1 1 calc R
C9 C 0.8645(3) 0.3358(2) 0.22911(19) 0.0407(5) Uani 1 1 d .
C3 C 0.6374(3) 0.6648(3) 0.36285(18) 0.0407(5) Uani 1 1 d .
N1 N 0.5724(2) 0.4144(2) 0.32638(19) 0.0461(4) Uani 1 1 d .
C8 C 0.7869(3) 0.5687(2) 0.35548(18) 0.0390(4) Uani 1 1 d .
C2 C 0.5022(3) 0.5648(3) 0.34352(19) 0.0423(5) Uani 1 1 d .
C1 C 0.7525(3) 0.3945(3) 0.3378(2) 0.0410(5) Uani 1 1 d .
C13 C 0.9166(3) 0.2974(3) 0.0220(2) 0.0510(5) Uani 1 1 d .
H13 H 0.8807 0.3106 -0.0517 0.061 Uiso 1 1 calc R
C7 C 0.9367(3) 0.6319(3) 0.3689(2) 0.0484(5) Uani 1 1 d .
H7 H 1.0379 0.5679 0.3632 0.058 Uiso 1 1 calc R
N2 N 1.3348(3) -0.0734(3) 0.1527(2) 0.0584(6) Uani 1 1 d .
C12 C 1.0733(3) 0.2207(3) 0.0346(2) 0.0445(5) Uani 1 1 d .
C5 C 0.7789(3) 0.8900(3) 0.4012(2) 0.0550(6) Uani 1 1 d .
H5 H 0.7778 0.9978 0.4181 0.066 Uiso 1 1 calc R
C11 C 1.1296(3) 0.2060(3) 0.14409(19) 0.0412(5) Uani 1 1 d .
C14 C 0.8132(3) 0.3546(3) 0.1186(2) 0.0479(5) Uani 1 1 d .
H14 H 0.7081 0.4063 0.1094 0.057 Uiso 1 1 calc R
C6 C 0.9305(3) 0.7950(3) 0.3913(2) 0.0550(6) Uani 1 1 d .
H6 H 1.0297 0.8415 0.3998 0.066 Uiso 1 1 calc R
H2B H 1.321(4) -0.146(4) 0.219(3) 0.076(10) Uiso 1 1 d .
H2C H 1.370(4) -0.096(4) 0.092(3) 0.077(11) Uiso 1 1 d .
H2A H 0.737(4) 0.321(4) 0.505(3) 0.071(9) Uiso 1 1 d .
H1 H 0.520(4) 0.340(4) 0.312(3) 0.069(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'
S S 0.1246 0.1234 '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
O3 S1 O4 118.36(12)
O3 S1 N2 108.61(13)
O4 S1 N2 108.59(12)
O3 S1 C11 106.07(10)
O4 S1 C11 107.81(11)
N2 S1 C11 106.83(11)
C5 C4 C3 117.5(2)
C11 C10 C9 120.7(2)
C14 C9 C10 119.11(19)
C14 C9 C1 122.03(18)
C10 C9 C1 118.86(19)
C8 C3 C4 121.8(2)
C8 C3 C2 108.33(18)
C4 C3 C2 129.90(19)
C2 N1 C1 113.83(19)
C7 C8 C3 121.04(19)
C7 C8 C1 129.26(18)
C3 C8 C1 109.64(18)
O1 C2 N1 125.7(2)
O1 C2 C3 127.05(19)
N1 C2 C3 107.20(18)
O2 C1 N1 111.54(17)
O2 C1 C8 111.23(17)
N1 C1 C8 100.77(16)
O2 C1 C9 106.50(16)
N1 C1 C9 112.64(18)
C8 C1 C9 114.27(17)
C14 C13 C12 120.2(2)
C8 C7 C6 117.4(2)
C13 C12 C11 119.9(2)
C13 C12 Cl1 118.31(18)
C11 C12 Cl1 121.77(17)
C4 C5 C6 120.9(2)
C10 C11 C12 119.4(2)
C10 C11 S1 118.24(17)
C12 C11 S1 122.35(16)
C13 C14 C9 120.7(2)
C5 C6 C7 121.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.4281(18)
S1 O4 1.4310(18)
S1 N2 1.595(2)
S1 C11 1.781(2)
Cl1 C12 1.727(2)
O2 C1 1.411(3)
O1 C2 1.242(3)
C4 C5 1.377(3)
C4 C3 1.384(3)
C10 C11 1.388(3)
C10 C9 1.391(3)
C9 C14 1.386(3)
C9 C1 1.520(3)
C3 C8 1.381(3)
C3 C2 1.467(3)
N1 C2 1.342(3)
N1 C1 1.466(3)
C8 C7 1.379(3)
C8 C1 1.517(3)
C13 C14 1.381(3)
C13 C12 1.383(3)
C7 C6 1.391(3)
C12 C11 1.397(3)
C5 C6 1.389(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 667689
