#------------------------------------------------------------------------------
#$Date: 2022-05-17 04:43:58 +0300 (Tue, 17 May 2022) $
#$Revision: 275475 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/26/2022608.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_2022608
loop_
_publ_author_name
'Kaspiaruk, Hanna'
'Checińska, Lilianna'
_publ_section_title
;
 A comparison of three crystalline forms of miconazole: solvent-free,
 ethanol monosolvate and hemihydrate
;
_journal_coeditor_code           VP3025
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229622004909
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C18 H14 Cl4 N2 O, C2 H6 O'
_chemical_formula_moiety         'C18 H14 Cl4 N2 O, C2 H6 O'
_chemical_formula_sum            'C20 H20 Cl4 N2 O2'
_chemical_formula_weight         462.18
_chemical_name_systematic
'(RS)-1-[2-(2,4-Dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole ethanol monosolvate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                115.423(3)
_cell_angle_beta                 99.068(2)
_cell_angle_gamma                94.776(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0766(2)
_cell_length_b                   11.5926(3)
_cell_length_c                   13.0383(4)
_cell_measurement_reflns_used    11675
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.6350
_cell_measurement_theta_min      2.6190
_cell_volume                     1073.06(6)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2021)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2021)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL2018 (Sheldrick, 2015b) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy Dualflex HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24180
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.591
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.570
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.749
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2021)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       prism
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.257
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         5130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0362
_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)+(0.0433P)²+0.1988P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0971
_reflns_number_gt                3866
_reflns_number_total             5130
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vp3025sup1.cif
_cod_data_source_block           MIC_EtOH
_cod_database_code               2022608
_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   0.919
_shelx_estimated_absorpt_t_max   0.978
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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 Cl1 0.14615(5) 0.08937(5) -0.05873(5) 0.07059(17) Uani d 1 . .
Cl Cl2 0.70773(7) -0.04509(5) -0.21679(5) 0.07166(17) Uani d 1 . .
Cl Cl3 0.67375(7) 0.26069(5) 0.46201(4) 0.06363(15) Uani d 1 . .
Cl Cl4 1.03341(6) 0.73384(5) 0.74446(4) 0.06272(15) Uani d 1 . .
O O1 0.48976(13) 0.43158(11) 0.23092(9) 0.0402(2) Uani d 1 . .
O O2 0.7124(2) 0.74307(17) 0.25280(15) 0.0777(5) Uani d 1 . .
N N1 0.21936(16) 0.52871(14) 0.13424(11) 0.0418(3) Uani d 1 . .
N N2 0.0041(2) 0.62447(17) 0.19415(14) 0.0586(4) Uani d 1 . .
C C1 0.37277(19) 0.34750(16) 0.12555(13) 0.0391(3) Uani d 1 . .
H H1 0.275927 0.306907 0.142209 0.047 Uiso calc 1 . .
C C2 0.3125(2) 0.43001(18) 0.06778(14) 0.0466(4) Uani d 1 . .
H H2A 0.410557 0.472184 0.055019 0.056 Uiso calc 1 . .
H H2B 0.239912 0.373782 -0.007706 0.056 Uiso calc 1 . .
C C3 0.0507(2) 0.51503(19) 0.12910(15) 0.0500(4) Uani d 1 . .
H H3 -0.024188 0.437205 0.084697 0.060 Uiso calc 1 . .
C C4 0.1519(3) 0.7116(2) 0.24283(19) 0.0661(5) Uani d 1 . .
H H4 0.159886 0.798734 0.293764 0.079 Uiso calc 1 . .
C C5 0.2853(3) 0.6544(2) 0.20713(18) 0.0614(5) Uani d 1 . .
H H5 0.398861 0.693353 0.228280 0.074 Uiso calc 1 . .
C C6 0.45550(18) 0.24380(16) 0.04228(13) 0.0382(3) Uani d 1 . .
C C7 0.36393(19) 0.12702(17) -0.04457(14) 0.0440(4) Uani d 1 . .
C C8 0.4390(2) 0.03650(17) -0.12479(15) 0.0494(4) Uani d 1 . .
H H8 0.375017 -0.041364 -0.182530 0.059 Uiso calc 1 . .
C C9 0.6109(2) 0.06525(17) -0.11646(15) 0.0475(4) Uani d 1 . .
C C10 0.7070(2) 0.17954(18) -0.03113(16) 0.0514(4) Uani d 1 . .
H H10 0.823274 0.197012 -0.026139 0.062 Uiso calc 1 . .
C C11 0.6286(2) 0.26845(17) 0.04737(14) 0.0461(4) Uani d 1 . .
H H11 0.693174 0.346293 0.104702 0.055 Uiso calc 1 . .
C C12 0.5327(2) 0.37092(16) 0.30356(13) 0.0396(3) Uani d 1 . .
H H12A 0.579419 0.293805 0.261831 0.048 Uiso calc 1 . .
H H12B 0.431301 0.345013 0.324908 0.048 Uiso calc 1 . .
C C13 0.66083(18) 0.46299(15) 0.41111(12) 0.0368(3) Uani d 1 . .
C C14 0.7314(2) 0.42108(16) 0.49085(13) 0.0402(3) Uani d 1 . .
C C15 0.8474(2) 0.50206(17) 0.59270(13) 0.0451(4) Uani d 1 . .
H H15 0.893305 0.471767 0.644574 0.054 Uiso calc 1 . .
C C16 0.8924(2) 0.62846(17) 0.61466(13) 0.0441(4) Uani d 1 . .
C C17 0.8280(2) 0.67429(17) 0.53826(15) 0.0485(4) Uani d 1 . .
H H17 0.861490 0.760103 0.554361 0.058 Uiso calc 1 . .
C C18 0.7119(2) 0.59063(17) 0.43642(14) 0.0447(4) Uani d 1 . .
H H18 0.667869 0.621257 0.384377 0.054 Uiso calc 1 . .
C C19 0.7899(4) 0.8659(3) 0.3475(3) 0.0888(8) Uani d 1 . .
H H19A 0.834458 0.922848 0.317696 0.107 Uiso calc 1 . .
H H19B 0.884063 0.854632 0.396659 0.107 Uiso calc 1 . .
C C20 0.6654(5) 0.9243(3) 0.4158(3) 0.1124(10) Uani d 1 . .
H H20A 0.575800 0.940105 0.368168 0.169 Uiso calc 1 . .
H H20B 0.720196 1.004767 0.481182 0.169 Uiso calc 1 . .
H H20C 0.618696 0.866454 0.442960 0.169 Uiso calc 1 . .
H H2 0.798(4) 0.705(3) 0.228(3) 0.120(11) Uiso d 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'
Cl Cl 0.1484 0.1585 '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'
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
C1 O1 C12 . . 112.51(12) ?
C19 O2 H2 . . 105(2) ?
C3 N1 C5 . . 106.99(15) ?
C3 N1 C2 . . 126.80(15) ?
C5 N1 C2 . . 126.07(15) ?
C3 N2 C4 . . 104.28(16) ?
O1 C1 C2 . . 107.00(13) ?
O1 C1 C6 . . 112.06(12) ?
C2 C1 C6 . . 107.83(12) ?
O1 C1 H1 . . 110.0 ?
C2 C1 H1 . . 110.0 ?
C6 C1 H1 . . 110.0 ?
N1 C2 C1 . . 114.19(12) ?
N1 C2 H2A . . 108.7 ?
C1 C2 H2A . . 108.7 ?
N1 C2 H2B . . 108.7 ?
C1 C2 H2B . . 108.7 ?
H2A C2 H2B . . 107.6 ?
N2 C3 N1 . . 112.10(17) ?
N2 C3 H3 . . 124.0 ?
N1 C3 H3 . . 124.0 ?
C5 C4 N2 . . 110.92(19) ?
C5 C4 H4 . . 124.5 ?
N2 C4 H4 . . 124.5 ?
C4 C5 N1 . . 105.72(18) ?
C4 C5 H5 . . 127.1 ?
N1 C5 H5 . . 127.1 ?
C7 C6 C11 . . 117.46(14) ?
C7 C6 C1 . . 122.84(13) ?
C11 C6 C1 . . 119.57(14) ?
C6 C7 C8 . . 122.37(14) ?
C6 C7 Cl1 . . 120.52(12) ?
C8 C7 Cl1 . . 117.10(13) ?
C9 C8 C7 . . 118.11(16) ?
C9 C8 H8 . . 120.9 ?
C7 C8 H8 . . 120.9 ?
C10 C9 C8 . . 121.51(15) ?
C10 C9 Cl2 . . 119.35(13) ?
C8 C9 Cl2 . . 119.15(13) ?
C9 C10 C11 . . 119.16(15) ?
C9 C10 H10 . . 120.4 ?
C11 C10 H10 . . 120.4 ?
C10 C11 C6 . . 121.39(15) ?
C10 C11 H11 . . 119.3 ?
C6 C11 H11 . . 119.3 ?
O1 C12 C13 . . 109.86(13) ?
O1 C12 H12A . . 109.7 ?
C13 C12 H12A . . 109.7 ?
O1 C12 H12B . . 109.7 ?
C13 C12 H12B . . 109.7 ?
H12A C12 H12B . . 108.2 ?
C18 C13 C14 . . 117.38(14) ?
C18 C13 C12 . . 122.69(14) ?
C14 C13 C12 . . 119.93(14) ?
C15 C14 C13 . . 122.61(15) ?
C15 C14 Cl3 . . 118.21(12) ?
C13 C14 Cl3 . . 119.18(12) ?
C16 C15 C14 . . 117.80(15) ?
C16 C15 H15 . . 121.1 ?
C14 C15 H15 . . 121.1 ?
C15 C16 C17 . . 121.88(15) ?
C15 C16 Cl4 . . 118.75(13) ?
C17 C16 Cl4 . . 119.36(14) ?
C16 C17 C18 . . 119.06(16) ?
C16 C17 H17 . . 120.5 ?
C18 C17 H17 . . 120.5 ?
C13 C18 C17 . . 121.24(15) ?
C13 C18 H18 . . 119.4 ?
C17 C18 H18 . . 119.4 ?
O2 C19 C20 . . 110.2(2) ?
O2 C19 H19A . . 109.6 ?
C20 C19 H19A . . 109.6 ?
O2 C19 H19B . . 109.6 ?
C20 C19 H19B . . 109.6 ?
H19A C19 H19B . . 108.1 ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
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
Cl1 C7 . 1.7375(16) ?
Cl2 C9 . 1.7355(16) ?
Cl3 C14 . 1.7366(17) ?
Cl4 C16 . 1.7434(16) ?
O1 C1 . 1.4205(18) ?
O1 C12 . 1.4215(18) ?
O2 C19 . 1.429(3) ?
O2 H2 . 0.88(3) ?
N1 C3 . 1.346(2) ?
N1 C5 . 1.354(2) ?
N1 C2 . 1.457(2) ?
N2 C3 . 1.314(2) ?
N2 C4 . 1.363(3) ?
C1 C2 . 1.516(2) ?
C1 C6 . 1.521(2) ?
C1 H1 . 0.9800 ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 H3 . 0.9300 ?
C4 C5 . 1.353(3) ?
C4 H4 . 0.9300 ?
C5 H5 . 0.9300 ?
C6 C7 . 1.384(2) ?
C6 C11 . 1.388(2) ?
C7 C8 . 1.388(2) ?
C8 C9 . 1.376(2) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.374(2) ?
C10 C11 . 1.385(2) ?
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 C13 . 1.500(2) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C18 . 1.380(2) ?
C13 C14 . 1.391(2) ?
C14 C15 . 1.383(2) ?
C15 C16 . 1.371(3) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.372(2) ?
C17 C18 . 1.390(2) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
C19 C20 . 1.464(4) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
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
O2 H2 N2 1_655 0.88(3) 1.99(3) 2.869(2) 172(3) yes
C5 H5 O2 . 0.93 2.49 3.398(3) 165.9 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
C12 O1 C1 C2 . . . . 169.42(12) ?
C12 O1 C1 C6 . . . . -72.58(15) ?
C3 N1 C2 C1 . . . . -88.93(19) ?
C5 N1 C2 C1 . . . . 95.9(2) ?
O1 C1 C2 N1 . . . . -63.34(17) ?
C6 C1 C2 N1 . . . . 175.94(14) ?
C4 N2 C3 N1 . . . . 0.0(2) ?
C5 N1 C3 N2 . . . . 0.1(2) ?
C2 N1 C3 N2 . . . . -175.75(15) ?
C3 N2 C4 C5 . . . . -0.1(2) ?
N2 C4 C5 N1 . . . . 0.2(2) ?
C3 N1 C5 C4 . . . . -0.2(2) ?
C2 N1 C5 C4 . . . . 175.75(16) ?
O1 C1 C6 C7 . . . . 156.72(15) ?
C2 C1 C6 C7 . . . . -85.78(19) ?
O1 C1 C6 C11 . . . . -27.4(2) ?
C2 C1 C6 C11 . . . . 90.08(17) ?
C11 C6 C7 C8 . . . . -0.2(3) ?
C1 C6 C7 C8 . . . . 175.77(15) ?
C11 C6 C7 Cl1 . . . . -178.97(13) ?
C1 C6 C7 Cl1 . . . . -3.0(2) ?
C6 C7 C8 C9 . . . . 0.1(3) ?
Cl1 C7 C8 C9 . . . . 178.91(14) ?
C7 C8 C9 C10 . . . . 0.4(3) ?
C7 C8 C9 Cl2 . . . . -179.12(14) ?
C8 C9 C10 C11 . . . . -0.8(3) ?
Cl2 C9 C10 C11 . . . . 178.75(14) ?
C9 C10 C11 C6 . . . . 0.7(3) ?
C7 C6 C11 C10 . . . . -0.2(3) ?
C1 C6 C11 C10 . . . . -176.29(16) ?
C1 O1 C12 C13 . . . . 178.03(11) ?
O1 C12 C13 C18 . . . . 5.8(2) ?
O1 C12 C13 C14 . . . . -175.05(12) ?
C18 C13 C14 C15 . . . . 0.6(2) ?
C12 C13 C14 C15 . . . . -178.61(14) ?
C18 C13 C14 Cl3 . . . . -179.05(12) ?
C12 C13 C14 Cl3 . . . . 1.79(19) ?
C13 C14 C15 C16 . . . . 0.3(2) ?
Cl3 C14 C15 C16 . . . . 179.90(12) ?
C14 C15 C16 C17 . . . . -1.1(2) ?
C14 C15 C16 Cl4 . . . . 178.10(11) ?
C15 C16 C17 C18 . . . . 0.9(2) ?
Cl4 C16 C17 C18 . . . . -178.22(13) ?
C14 C13 C18 C17 . . . . -0.7(2) ?
C12 C13 C18 C17 . . . . 178.45(15) ?
C16 C17 C18 C13 . . . . 0.0(2) ?

_cod_database_fobs_code 2022608
