#------------------------------------------------------------------------------
#$Date: 2022-05-17 04:43:58 +0300 (Tue, 17 May 2022) $
#$Revision: 275475 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/26/2022607.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_2022607
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'
_chemical_formula_moiety         'C18 H14 Cl4 N2 O'
_chemical_formula_sum            'C18 H14 Cl4 N2 O'
_chemical_formula_weight         416.11
_chemical_name_systematic
(RS)-1-[2-(2,4-Dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 102.814(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1902(5)
_cell_length_b                   18.5341(8)
_cell_length_c                   14.2507(7)
_cell_measurement_reflns_used    6096
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.6330
_cell_measurement_theta_min      2.6320
_cell_volume                     1851.81(18)
_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 0.976
_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  0.0567
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7789
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         2.642
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2021)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.206
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.883
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         7789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.883
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0683P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1384
_reflns_number_gt                3850
_reflns_number_total             7789
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vp3025sup1.cif
_cod_data_source_block           MIC
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2022607
_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   0.909
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.68824(15) 0.17840(5) 0.66591(6) 0.0804(3) Uani d 1 . .
Cl Cl2 0.68906(15) 0.46252(5) 0.59908(7) 0.0794(3) Uani d 1 . .
Cl Cl3 0.24762(17) 0.01407(5) 0.22361(8) 0.0892(3) Uani d 1 . .
Cl Cl4 0.08129(14) 0.16042(7) -0.10809(7) 0.0957(4) Uani d 1 . .
O O1 0.5211(3) 0.15622(11) 0.34559(14) 0.0559(5) Uani d 1 . .
N N1 0.7834(4) 0.04527(14) 0.43453(19) 0.0580(6) Uani d 1 . .
N N2 0.7429(4) -0.07207(18) 0.4525(3) 0.0828(10) Uani d 1 . .
C C1 0.6057(4) 0.15782(16) 0.4462(2) 0.0515(7) Uani d 1 . .
H H1 0.527172 0.129766 0.481121 0.062 Uiso calc 1 . .
C C2 0.7990(4) 0.12183(17) 0.4569(2) 0.0596(8) Uani d 1 . .
H H2A 0.868596 0.145360 0.414468 0.072 Uiso calc 1 . .
H H2B 0.871349 0.128103 0.522479 0.072 Uiso calc 1 . .
C C3 0.7542(5) -0.0085(2) 0.4926(3) 0.0739(10) Uani d 1 . .
H H3 0.742981 -0.001151 0.555641 0.089 Uiso calc 1 . .
C C4 0.7670(6) -0.0579(2) 0.3628(3) 0.0925(13) Uani d 1 . .
H H4 0.765698 -0.092567 0.315486 0.111 Uiso calc 1 . .
C C5 0.7930(7) 0.0128(2) 0.3513(3) 0.0886(12) Uani d 1 . .
H H5 0.813746 0.035301 0.296112 0.106 Uiso calc 1 . .
C C6 0.6268(4) 0.23446(16) 0.4851(2) 0.0503(7) Uani d 1 . .
C C7 0.6635(4) 0.24907(17) 0.5833(2) 0.0546(7) Uani d 1 . .
C C8 0.6819(4) 0.31846(18) 0.6198(2) 0.0587(8) Uani d 1 . .
H H8 0.705115 0.326855 0.685736 0.070 Uiso calc 1 . .
C C9 0.6646(4) 0.37477(17) 0.5553(2) 0.0579(8) Uani d 1 . .
C C10 0.6300(5) 0.36308(18) 0.4577(2) 0.0602(8) Uani d 1 . .
H H10 0.619176 0.401724 0.415225 0.072 Uiso calc 1 . .
C C11 0.6117(4) 0.29330(16) 0.4239(2) 0.0559(7) Uani d 1 . .
H H11 0.588458 0.285396 0.357855 0.067 Uiso calc 1 . .
C C12 0.3171(4) 0.16181(18) 0.3241(2) 0.0598(8) Uani d 1 . .
H H12A 0.278459 0.206467 0.349735 0.072 Uiso calc 1 . .
H H12B 0.262363 0.121804 0.352604 0.072 Uiso calc 1 . .
C C13 0.2501(4) 0.16037(16) 0.2166(2) 0.0530(7) Uani d 1 . .
C C14 0.2189(4) 0.09641(16) 0.1643(2) 0.0566(7) Uani d 1 . .
C C15 0.1655(4) 0.0963(2) 0.0652(2) 0.0646(8) Uani d 1 . .
H H15 0.143930 0.052975 0.031537 0.078 Uiso calc 1 . .
C C16 0.1448(4) 0.1607(2) 0.0169(2) 0.0643(9) Uani d 1 . .
C C17 0.1735(5) 0.2258(2) 0.0659(3) 0.0667(9) Uani d 1 . .
H H17 0.158809 0.269406 0.032798 0.080 Uiso calc 1 . .
C C18 0.2242(4) 0.22397(17) 0.1647(2) 0.0630(8) Uani d 1 . .
H H18 0.241914 0.267442 0.198140 0.076 Uiso calc 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 . . 113.6(2) ?
C3 N1 C5 . . 104.9(3) ?
C3 N1 C2 . . 127.2(3) ?
C5 N1 C2 . . 127.8(3) ?
C3 N2 C4 . . 103.3(3) ?
O1 C1 C2 . . 105.5(2) ?
O1 C1 C6 . . 111.8(2) ?
C2 C1 C6 . . 111.0(2) ?
O1 C1 H1 . . 109.5 ?
C2 C1 H1 . . 109.5 ?
C6 C1 H1 . . 109.5 ?
N1 C2 C1 . . 112.5(3) ?
N1 C2 H2A . . 109.1 ?
C1 C2 H2A . . 109.1 ?
N1 C2 H2B . . 109.1 ?
C1 C2 H2B . . 109.1 ?
H2A C2 H2B . . 107.8 ?
N2 C3 N1 . . 113.9(4) ?
N2 C3 H3 . . 123.1 ?
N1 C3 H3 . . 123.1 ?
C5 C4 N2 . . 110.9(4) ?
C5 C4 H4 . . 124.6 ?
N2 C4 H4 . . 124.6 ?
C4 C5 N1 . . 107.0(4) ?
C4 C5 H5 . . 126.5 ?
N1 C5 H5 . . 126.5 ?
C11 C6 C7 . . 116.8(3) ?
C11 C6 C1 . . 121.2(2) ?
C7 C6 C1 . . 122.0(3) ?
C8 C7 C6 . . 122.7(3) ?
C8 C7 Cl1 . . 117.2(2) ?
C6 C7 Cl1 . . 120.1(2) ?
C9 C8 C7 . . 117.8(3) ?
C9 C8 H8 . . 121.1 ?
C7 C8 H8 . . 121.1 ?
C10 C9 C8 . . 121.7(3) ?
C10 C9 Cl2 . . 119.5(3) ?
C8 C9 Cl2 . . 118.8(2) ?
C9 C10 C11 . . 119.0(3) ?
C9 C10 H10 . . 120.5 ?
C11 C10 H10 . . 120.5 ?
C10 C11 C6 . . 122.1(3) ?
C10 C11 H11 . . 119.0 ?
C6 C11 H11 . . 119.0 ?
O1 C12 C13 . . 107.4(2) ?
O1 C12 H12A . . 110.2 ?
C13 C12 H12A . . 110.2 ?
O1 C12 H12B . . 110.2 ?
C13 C12 H12B . . 110.2 ?
H12A C12 H12B . . 108.5 ?
C18 C13 C14 . . 117.0(3) ?
C18 C13 C12 . . 120.4(3) ?
C14 C13 C12 . . 122.6(3) ?
C15 C14 C13 . . 121.7(3) ?
C15 C14 Cl3 . . 118.3(3) ?
C13 C14 Cl3 . . 120.1(2) ?
C16 C15 C14 . . 119.2(3) ?
C16 C15 H15 . . 120.4 ?
C14 C15 H15 . . 120.4 ?
C15 C16 C17 . . 121.2(3) ?
C15 C16 Cl4 . . 119.2(3) ?
C17 C16 Cl4 . . 119.6(3) ?
C18 C17 C16 . . 118.1(3) ?
C18 C17 H17 . . 121.0 ?
C16 C17 H17 . . 121.0 ?
C17 C18 C13 . . 122.8(3) ?
C17 C18 H18 . . 118.6 ?
C13 C18 H18 . . 118.6 ?
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 . 1.744(3) ?
Cl2 C9 . 1.737(3) ?
Cl3 C14 . 1.734(3) ?
Cl4 C16 . 1.738(3) ?
O1 C1 . 1.429(3) ?
O1 C12 . 1.434(3) ?
N1 C3 . 1.341(5) ?
N1 C5 . 1.346(5) ?
N1 C2 . 1.453(4) ?
N2 C3 . 1.303(5) ?
N2 C4 . 1.354(6) ?
C1 C2 . 1.519(4) ?
C1 C6 . 1.520(4) ?
C1 H1 . 0.9800 ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 H3 . 0.9300 ?
C4 C5 . 1.339(6) ?
C4 H4 . 0.9300 ?
C5 H5 . 0.9300 ?
C6 C11 . 1.386(4) ?
C6 C7 . 1.391(4) ?
C7 C8 . 1.383(4) ?
C8 C9 . 1.379(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.374(4) ?
C10 C11 . 1.376(4) ?
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 C13 . 1.500(4) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C18 . 1.382(4) ?
C13 C14 . 1.392(4) ?
C14 C15 . 1.380(4) ?
C15 C16 . 1.369(5) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.386(5) ?
C17 C18 . 1.376(5) ?
C17 H17 . 0.9300 ?
C18 H18 . 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
C1 H1 N2 3_656 0.98 2.57 3.534(4) 166.7 yes
C5 H5 Cl2 4_565 0.93 2.75 3.534(4) 142.3 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 . . . . 157.6(2) ?
C12 O1 C1 C6 . . . . -81.7(3) ?
C3 N1 C2 C1 . . . . -81.5(4) ?
C5 N1 C2 C1 . . . . 97.7(4) ?
O1 C1 C2 N1 . . . . -67.7(3) ?
C6 C1 C2 N1 . . . . 171.0(3) ?
C4 N2 C3 N1 . . . . 0.1(4) ?
C5 N1 C3 N2 . . . . -0.6(4) ?
C2 N1 C3 N2 . . . . 178.8(3) ?
C3 N2 C4 C5 . . . . 0.4(5) ?
N2 C4 C5 N1 . . . . -0.7(5) ?
C3 N1 C5 C4 . . . . 0.7(4) ?
C2 N1 C5 C4 . . . . -178.6(3) ?
O1 C1 C6 C11 . . . . -15.6(4) ?
C2 C1 C6 C11 . . . . 101.9(3) ?
O1 C1 C6 C7 . . . . 164.9(2) ?
C2 C1 C6 C7 . . . . -77.6(4) ?
C11 C6 C7 C8 . . . . 0.9(4) ?
C1 C6 C7 C8 . . . . -179.6(3) ?
C11 C6 C7 Cl1 . . . . -179.1(2) ?
C1 C6 C7 Cl1 . . . . 0.4(4) ?
C6 C7 C8 C9 . . . . -0.7(5) ?
Cl1 C7 C8 C9 . . . . 179.3(2) ?
C7 C8 C9 C10 . . . . 0.1(5) ?
C7 C8 C9 Cl2 . . . . -179.4(2) ?
C8 C9 C10 C11 . . . . 0.2(5) ?
Cl2 C9 C10 C11 . . . . 179.7(3) ?
C9 C10 C11 C6 . . . . 0.1(5) ?
C7 C6 C11 C10 . . . . -0.6(4) ?
C1 C6 C11 C10 . . . . 179.9(3) ?
C1 O1 C12 C13 . . . . 179.2(2) ?
O1 C12 C13 C18 . . . . -92.5(3) ?
O1 C12 C13 C14 . . . . 84.9(3) ?
C18 C13 C14 C15 . . . . 0.3(5) ?
C12 C13 C14 C15 . . . . -177.1(3) ?
C18 C13 C14 Cl3 . . . . -179.9(2) ?
C12 C13 C14 Cl3 . . . . 2.7(4) ?
C13 C14 C15 C16 . . . . 0.7(5) ?
Cl3 C14 C15 C16 . . . . -179.1(2) ?
C14 C15 C16 C17 . . . . -1.0(5) ?
C14 C15 C16 Cl4 . . . . 179.0(2) ?
C15 C16 C17 C18 . . . . 0.2(5) ?
Cl4 C16 C17 C18 . . . . -179.8(2) ?
C16 C17 C18 C13 . . . . 0.9(5) ?
C14 C13 C18 C17 . . . . -1.2(5) ?
C12 C13 C18 C17 . . . . 176.3(3) ?

_cod_database_fobs_code 2022607
