#------------------------------------------------------------------------------
#$Date: 2025-01-01 05:35:38 +0200 (Wed, 01 Jan 2025) $
#$Revision: 297029 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/33/2023341.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_2023341
loop_
_publ_author_name
'Ben, Anna'
'Chęcińska, Lilianna'
_publ_section_title
;
 Crystal structure of luliconazole
;
_journal_coeditor_code           VM2310
_journal_issue                   1
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first              24
_journal_page_last               28
_journal_paper_doi               10.1107/S2056989024011812
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          'C14 H9 Cl2 N3 S2'
_chemical_formula_moiety         'C14 H9 Cl2 N3 S2'
_chemical_formula_sum            'C14 H9 Cl2 N3 S2'
_chemical_formula_weight         354.26
_chemical_name_common
;
Luliconazole
;
_chemical_name_systematic
(E)-[(4R)-4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene](1H-imidazol-1-yl)acetonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2019/2
_cell_angle_alpha                90
_cell_angle_beta                 95.7780(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.01360(10)
_cell_length_b                   8.15610(10)
_cell_length_c                   10.87180(10)
_cell_measurement_reflns_used    12732
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      76.5520
_cell_measurement_theta_min      4.0620
_cell_volume                     795.189(15)
_computing_cell_refinement
;
CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)
;
_computing_data_collection
;
CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)
;
_computing_data_reduction
;
CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020) and PLATON (Spek, 2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2019/2 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14902
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.156
_diffrn_reflns_theta_min         4.087
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    6.087
_exptl_absorpt_correction_T_max  0.787
_exptl_absorpt_correction_T_min  0.167
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2023)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.190
_refine_ls_abs_structure_details
;
Flack x determined using 1322 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   -0.010(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3132
_refine_ls_number_restraints     295
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0249
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0399P)²+0.0887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0693
_reflns_number_gt                3031
_reflns_number_total             3132
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vm2310.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2023341
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.376
_shelx_estimated_absorpt_t_max   0.838
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1A 0.7112(8) 0.3287(9) 1.1135(7) 0.0901(16) Uani d 0.5 A 1
Cl Cl2A 1.2841(5) 0.2715(10) 1.0208(5) 0.0882(15) Uani d 0.5 A 1
Cl Cl1B 0.7057(9) 0.2672(10) 1.1114(7) 0.114(3) Uani d 0.5 B 2
Cl Cl2B 1.2743(5) 0.3102(11) 1.0307(6) 0.105(2) Uani d 0.5 B 2
S S1 0.39907(7) 0.21429(7) 0.66512(6) 0.05387(17) Uani d 1 . .
S S2 0.59952(8) 0.49155(9) 0.73496(7) 0.0642(2) Uani d 1 . .
N N1 0.4012(3) 0.8370(3) 0.6007(3) 0.0670(6) Uani d 1 . .
N N2 0.2121(2) 0.4772(3) 0.51520(18) 0.0454(4) Uani d 1 . .
N N3 0.0737(3) 0.3647(3) 0.3584(2) 0.0658(7) Uani d 1 . .
C C1 0.3416(2) 0.5289(3) 0.5913(2) 0.0436(5) Uani d 1 . .
C C2 0.3726(3) 0.6999(3) 0.5944(2) 0.0488(5) Uani d 1 . .
C C3 0.2085(3) 0.3786(3) 0.4141(2) 0.0531(6) Uani d 1 . .
H H3 0.291839 0.327232 0.387726 0.064 Uiso calc 1 . .
C C4 -0.0127(3) 0.4596(4) 0.4260(3) 0.0724(9) Uani d 1 . .
H H4 -0.114889 0.473964 0.407721 0.087 Uiso calc 1 . .
C C5 0.0686(3) 0.5297(4) 0.5224(3) 0.0615(7) Uani d 1 . .
H H5 0.034806 0.599083 0.581389 0.074 Uiso calc 1 . .
C C6 0.4336(3) 0.4234(3) 0.6568(2) 0.0454(5) Uani d 1 . .
C C7 0.5759(3) 0.1646(4) 0.7514(3) 0.0624(7) Uani d 1 . .
H H7A 0.564313 0.069235 0.802923 0.075 Uiso calc 1 . .
H H7B 0.649020 0.138719 0.694683 0.075 Uiso calc 1 . .
C C8 0.6294(3) 0.3087(4) 0.8315(2) 0.0559(6) Uani d 1 . .
H H8 0.566602 0.317007 0.899744 0.067 Uiso calc 1 C 1
C C9A 0.7953(5) 0.2935(9) 0.8872(7) 0.0553(13) Uani d 0.5 A 1
C C10A 0.8435(7) 0.3149(11) 1.0117(7) 0.0556(14) Uani d 0.5 A 1
C C11A 0.9949(8) 0.3097(11) 1.0515(5) 0.0628(14) Uani d 0.5 A 1
H H11A 1.027154 0.324001 1.134743 0.075 Uiso calc 0.5 A 1
C C12A 1.0981(5) 0.2832(9) 0.9668(7) 0.0683(14) Uani d 0.5 A 1
C C13A 1.0499(6) 0.2618(8) 0.8423(6) 0.0619(14) Uani d 0.5 A 1
H H13A 1.118888 0.244023 0.785627 0.074 Uiso calc 0.5 A 1
C C14A 0.8985(7) 0.2670(7) 0.8025(5) 0.0579(14) Uani d 0.5 A 1
H H14A 0.866205 0.252683 0.719235 0.069 Uiso calc 0.5 A 1
C C9B 0.7923(5) 0.3066(9) 0.8760(7) 0.0528(13) Uani d 0.5 B 2
C C10B 0.8287(7) 0.2829(11) 1.0020(7) 0.0566(14) Uani d 0.5 B 2
C C11B 0.9773(8) 0.2807(11) 1.0507(5) 0.0646(14) Uani d 0.5 B 2
H H11B 1.001705 0.264790 1.135003 0.077 Uiso calc 0.5 B 2
C C12B 1.0895(5) 0.3021(9) 0.9733(7) 0.0632(13) Uani d 0.5 B 2
C C13B 1.0531(6) 0.3258(8) 0.8473(7) 0.0648(14) Uani d 0.5 B 2
H H13B 1.128176 0.340176 0.795514 0.078 Uiso calc 0.5 B 2
C C14B 0.9045(7) 0.3281(8) 0.7986(5) 0.0602(14) Uani d 0.5 B 2
H H14B 0.880120 0.343952 0.714286 0.072 Uiso calc 0.5 B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C6 S1 C7 . . 95.38(13) ?
C6 S2 C8 . . 95.13(12) ?
C3 N2 C5 . . 106.5(2) ?
C3 N2 C1 . . 126.6(2) ?
C5 N2 C1 . . 126.6(2) ?
C3 N3 C4 . . 104.8(2) ?
C6 C1 C2 . . 120.3(2) ?
C6 C1 N2 . . 122.8(2) ?
C2 C1 N2 . . 116.8(2) ?
N1 C2 C1 . . 177.5(3) ?
N3 C3 N2 . . 111.8(2) ?
N3 C3 H3 . . 124.1 ?
N2 C3 H3 . . 124.1 ?
C5 C4 N3 . . 111.4(2) ?
C5 C4 H4 . . 124.3 ?
N3 C4 H4 . . 124.3 ?
C4 C5 N2 . . 105.4(3) ?
C4 C5 H5 . . 127.3 ?
N2 C5 H5 . . 127.3 ?
C1 C6 S2 . . 120.55(19) ?
C1 C6 S1 . . 123.39(19) ?
S2 C6 S1 . . 116.03(14) ?
C8 C7 S1 . . 109.7(2) ?
C8 C7 H7A . . 109.7 ?
S1 C7 H7A . . 109.7 ?
C8 C7 H7B . . 109.7 ?
S1 C7 H7B . . 109.7 ?
H7A C7 H7B . . 108.2 ?
C9B C8 C7 . . 115.0(4) ?
C7 C8 C9A . . 113.5(3) ?
C9B C8 S2 . . 106.1(3) ?
C7 C8 S2 . . 106.49(17) ?
C9A C8 S2 . . 111.6(3) ?
C7 C8 H8 . . 108.4 ?
C9A C8 H8 . . 108.4 ?
S2 C8 H8 . . 108.4 ?
C10A C9A C14A . . 120.0 ?
C10A C9A C8 . . 124.2(5) ?
C14A C9A C8 . . 115.7(5) ?
C11A C10A C9A . . 120.0 ?
C11A C10A Cl1A . . 121.8(6) ?
C9A C10A Cl1A . . 117.9(5) ?
C10A C11A C12A . . 120.0 ?
C10A C11A H11A . . 120.0 ?
C12A C11A H11A . . 120.0 ?
C13A C12A C11A . . 120.0 ?
C13A C12A Cl2A . . 121.5(5) ?
C11A C12A Cl2A . . 118.4(5) ?
C12A C13A C14A . . 120.0 ?
C12A C13A H13A . . 120.0 ?
C14A C13A H13A . . 120.0 ?
C13A C14A C9A . . 120.0 ?
C13A C14A H14A . . 120.0 ?
C9A C14A H14A . . 120.0 ?
C10B C9B C14B . . 120.0 ?
C10B C9B C8 . . 116.5(5) ?
C14B C9B C8 . . 123.5(5) ?
C11B C10B C9B . . 120.0 ?
C11B C10B Cl1B . . 113.7(6) ?
C9B C10B Cl1B . . 126.2(6) ?
C10B C11B C12B . . 120.0 ?
C10B C11B H11B . . 120.0 ?
C12B C11B H11B . . 120.0 ?
C11B C12B C13B . . 120.0 ?
C11B C12B Cl2B . . 121.5(5) ?
C13B C12B Cl2B . . 118.4(5) ?
C14B C13B C12B . . 120.0 ?
C14B C13B H13B . . 120.0 ?
C12B C13B H13B . . 120.0 ?
C13B C14B C9B . . 120.0 ?
C13B C14B H14B . . 120.0 ?
C9B C14B H14B . . 120.0 ?
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
Cl1A C10A . 1.711(3) ?
Cl2A C12A . 1.722(3) ?
Cl1B C10B . 1.710(3) ?
Cl2B C12B . 1.720(3) ?
S1 C6 . 1.737(3) ?
S1 C7 . 1.812(3) ?
S2 C6 . 1.736(2) ?
S2 C8 . 1.828(3) ?
N1 C2 . 1.148(4) ?
N2 C3 . 1.360(3) ?
N2 C5 . 1.371(3) ?
N2 C1 . 1.425(3) ?
N3 C3 . 1.306(3) ?
N3 C4 . 1.364(4) ?
C1 C6 . 1.348(3) ?
C1 C2 . 1.422(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.344(4) ?
C4 H4 . 0.9300 ?
C5 H5 . 0.9300 ?
C7 C8 . 1.512(4) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9B . 1.499(5) ?
C8 C9A . 1.561(5) ?
C8 H8 . 0.9800 ?
C9A C10A . 1.3900 ?
C9A C14A . 1.3900 ?
C10A C11A . 1.3900 ?
C11A C12A . 1.3900 ?
C11A H11A . 0.9300 ?
C12A C13A . 1.3900 ?
C13A C14A . 1.3900 ?
C13A H13A . 0.9300 ?
C14A H14A . 0.9300 ?
C9B C10B . 1.3900 ?
C9B C14B . 1.3900 ?
C10B C11B . 1.3900 ?
C11B C12B . 1.3900 ?
C11B H11B . 0.9300 ?
C12B C13B . 1.3900 ?
C13B C14B . 1.3900 ?
C13B H13B . 0.9300 ?
C14B H14B . 0.9300 ?
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
_geom_hbond_publ_flag
C5 H5 N3 2_556 0.93 2.49 3.335(4) 151 yes
C11A H11A N3 1_656 0.93 2.45 3.371(6) 172 yes
C11B H11B N3 1_656 0.93 2.58 3.440(6) 154 yes
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 N2 C1 C6 . . . . -62.6(4) ?
C5 N2 C1 C6 . . . . 124.2(3) ?
C3 N2 C1 C2 . . . . 116.4(3) ?
C5 N2 C1 C2 . . . . -56.8(4) ?
C4 N3 C3 N2 . . . . 0.6(3) ?
C5 N2 C3 N3 . . . . -0.5(3) ?
C1 N2 C3 N3 . . . . -174.8(2) ?
C3 N3 C4 C5 . . . . -0.4(4) ?
N3 C4 C5 N2 . . . . 0.1(4) ?
C3 N2 C5 C4 . . . . 0.2(3) ?
C1 N2 C5 C4 . . . . 174.5(3) ?
C2 C1 C6 S2 . . . . -5.7(3) ?
N2 C1 C6 S2 . . . . 173.31(18) ?
C2 C1 C6 S1 . . . . 176.36(19) ?
N2 C1 C6 S1 . . . . -4.7(3) ?
C8 S2 C6 C1 . . . . 164.4(2) ?
C8 S2 C6 S1 . . . . -17.54(17) ?
C7 S1 C6 C1 . . . . 174.3(2) ?
C7 S1 C6 S2 . . . . -3.76(18) ?
C6 S1 C7 C8 . . . . 29.9(2) ?
S1 C7 C8 C9B . . . . -161.5(4) ?
S1 C7 C8 C9A . . . . -167.4(4) ?
S1 C7 C8 S2 . . . . -44.3(2) ?
C6 S2 C8 C9B . . . . 159.7(3) ?
C6 S2 C8 C7 . . . . 36.8(2) ?
C6 S2 C8 C9A . . . . 161.1(3) ?
C7 C8 C9A C10A . . . . -129.6(4) ?
S2 C8 C9A C10A . . . . 110.0(4) ?
C7 C8 C9A C14A . . . . 54.5(5) ?
S2 C8 C9A C14A . . . . -65.9(5) ?
C14A C9A C10A C11A . . . . 0.0 ?
C8 C9A C10A C11A . . . . -175.7(6) ?
C14A C9A C10A Cl1A . . . . -174.2(7) ?
C8 C9A C10A Cl1A . . . . 10.0(6) ?
C9A C10A C11A C12A . . . . 0.0 ?
Cl1A C10A C11A C12A . . . . 174.0(7) ?
C10A C11A C12A C13A . . . . 0.0 ?
C10A C11A C12A Cl2A . . . . -178.1(6) ?
C11A C12A C13A C14A . . . . 0.0 ?
Cl2A C12A C13A C14A . . . . 178.0(6) ?
C12A C13A C14A C9A . . . . 0.0 ?
C10A C9A C14A C13A . . . . 0.0 ?
C8 C9A C14A C13A . . . . 176.1(6) ?
C7 C8 C9B C10B . . . . -111.8(4) ?
S2 C8 C9B C10B . . . . 130.8(3) ?
C7 C8 C9B C14B . . . . 68.7(6) ?
S2 C8 C9B C14B . . . . -48.7(5) ?
C14B C9B C10B C11B . . . . 0.0 ?
C8 C9B C10B C11B . . . . -179.5(6) ?
C14B C9B C10B Cl1B . . . . 175.7(7) ?
C8 C9B C10B Cl1B . . . . -3.8(7) ?
C9B C10B C11B C12B . . . . 0.0 ?
Cl1B C10B C11B C12B . . . . -176.2(7) ?
C10B C11B C12B C13B . . . . 0.0 ?
C10B C11B C12B Cl2B . . . . 176.8(7) ?
C11B C12B C13B C14B . . . . 0.0 ?
Cl2B C12B C13B C14B . . . . -176.9(6) ?
C12B C13B C14B C9B . . . . 0.0 ?
C10B C9B C14B C13B . . . . 0.0 ?
C8 C9B C14B C13B . . . . 179.5(6) ?
