#------------------------------------------------------------------------------
#$Date: 2022-12-20 12:58:25 +0200 (Tue, 20 Dec 2022) $
#$Revision: 279947 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/26/2022609.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_2022609
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, 0.5 H2 O'
_chemical_formula_moiety         'C18 H14 Cl4 N2 O, 0.5(H2 O)'
_chemical_formula_sum            'C18 H15 Cl4 N2 O1.5'
_chemical_formula_weight         425.12
_chemical_name_systematic
'(RS)-1-[2-(2,4-Dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole hemihydrate'
_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   mixed
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 117.864(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.0630(3)
_cell_length_b                   33.2610(16)
_cell_length_c                   16.5481(7)
_cell_measurement_reflns_used    11558
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.0300
_cell_measurement_theta_min      2.6100
_cell_volume                     3923.4(3)
_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 0.985
_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  0.0477
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            45202
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         2.449
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2021)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       needle
_exptl_crystal_F_000             1736
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.275
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     468
_refine_ls_number_reflns         9339
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0448
_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)+(0.0381P)²+1.3220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1077
_reflns_number_gt                6260
_reflns_number_total             9339
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vp3025sup1.cif
_cod_data_source_block           MIC_0.5H2O
_cod_depositor_comments
;

2022-12-20
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C36 H30 Cl8 N4 O3'
_cod_original_formula_weight         850.24
_cod_original_formula_moiety         '2(C18 H14 Cl4 N2 O), H2 O'
_cod_original_formula_iupac          '2C18 H14 Cl4 N2 O, H2 O'
_cod_original_formula_units_Z            4
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2022609
_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   0.930
_shelx_estimated_absorpt_t_max   0.976
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 0.70158(7) 0.20292(2) 0.64935(4) 0.05809(16) Uani d 1 . .
Cl Cl2 0.18072(9) 0.19687(2) 0.76263(5) 0.07108(19) Uani d 1 . .
Cl Cl3 0.24111(13) 0.02107(2) 0.41323(6) 0.0960(3) Uani d 1 . .
Cl Cl4 -0.32437(12) 0.02855(3) 0.07000(6) 0.1052(3) Uani d 1 . .
Cl Cl5 0.68527(7) 0.09835(2) -0.28394(4) 0.05897(16) Uani d 1 . .
Cl Cl6 1.22207(9) 0.06365(2) -0.37584(4) 0.07210(19) Uani d 1 . .
Cl Cl7 1.22930(12) -0.00976(2) 0.13554(5) 0.0890(2) Uani d 1 . .
Cl Cl8 1.78209(11) 0.06398(3) 0.42507(5) 0.1083(3) Uani d 1 . .
O O1 0.2630(2) 0.15330(4) 0.38629(9) 0.0559(4) Uani d 1 . .
O O2 1.1467(2) 0.10884(4) 0.00241(9) 0.0508(4) Uani d 1 . .
O O3 0.3841(3) 0.20511(8) 0.04599(18) 0.0917(6) Uani d 1 . .
N N1 0.4930(3) 0.21547(6) 0.36275(12) 0.0548(5) Uani d 1 . .
N N2 0.5342(5) 0.20483(7) 0.24160(18) 0.0865(7) Uani d 1 . .
N N3 0.8862(3) 0.17374(6) -0.04043(12) 0.0569(5) Uani d 1 . .
N N4 0.6856(4) 0.18401(9) 0.01256(18) 0.0895(8) Uani d 1 . .
C C1 0.3960(3) 0.17619(6) 0.46075(14) 0.0480(5) Uani d 1 . .
H H1 0.519448 0.163330 0.485287 0.058 Uiso calc 1 . .
C C2 0.4030(3) 0.21731(6) 0.42105(15) 0.0541(5) Uani d 1 . .
H H2A 0.276182 0.227428 0.385827 0.065 Uiso calc 1 . .
H H2B 0.471043 0.235987 0.470714 0.065 Uiso calc 1 . .
C C3 0.4140(4) 0.20459(8) 0.27436(17) 0.0702(7) Uani d 1 . .
H H3 0.288298 0.197663 0.240204 0.084 Uiso calc 1 . .
C C4 0.6982(5) 0.21632(10) 0.3132(3) 0.0884(9) Uani d 1 . .
H H4 0.810644 0.219201 0.310936 0.106 Uiso calc 1 . .
C C5 0.6772(4) 0.22302(9) 0.3883(2) 0.0737(7) Uani d 1 . .
H H5 0.769185 0.231124 0.445610 0.088 Uiso calc 1 . .
C C6 0.3409(3) 0.18091(6) 0.53656(13) 0.0430(4) Uani d 1 . .
C C7 0.4697(3) 0.19338(6) 0.62376(13) 0.0419(4) Uani d 1 . .
C C8 0.4231(3) 0.19842(6) 0.69335(14) 0.0452(5) Uani d 1 . .
H H8 0.512332 0.206794 0.751067 0.054 Uiso calc 1 . .
C C9 0.2407(3) 0.19072(7) 0.67517(15) 0.0490(5) Uani d 1 . .
C C10 0.1075(3) 0.17834(7) 0.58965(16) 0.0572(6) Uani d 1 . .
H H10 -0.014826 0.173090 0.578278 0.069 Uiso calc 1 . .
C C11 0.1583(3) 0.17386(7) 0.52126(15) 0.0547(5) Uani d 1 . .
H H11 0.068128 0.165922 0.463381 0.066 Uiso calc 1 . .
C C12 0.2773(3) 0.11100(7) 0.40170(16) 0.0587(6) Uani d 1 . .
H H12A 0.262042 0.104702 0.455093 0.070 Uiso calc 1 . .
H H12B 0.399648 0.101554 0.412365 0.070 Uiso calc 1 . .
C C13 0.1262(3) 0.09079(7) 0.31868(16) 0.0533(5) Uani d 1 . .
C C14 0.0981(4) 0.04955(7) 0.31723(17) 0.0626(6) Uani d 1 . .
C C15 -0.0402(4) 0.03025(8) 0.2416(2) 0.0726(7) Uani d 1 . .
H H15 -0.057407 0.002628 0.242215 0.087 Uiso calc 1 . .
C C16 -0.1511(4) 0.05258(9) 0.16603(19) 0.0697(7) Uani d 1 . .
C C17 -0.1293(4) 0.09312(8) 0.16416(18) 0.0709(7) Uani d 1 . .
H H17 -0.206216 0.107970 0.112438 0.085 Uiso calc 1 . .
C C18 0.0099(3) 0.11188(8) 0.24084(16) 0.0634(6) Uani d 1 . .
H H18 0.025136 0.139557 0.239674 0.076 Uiso calc 1 . .
C C21 1.0023(3) 0.11427(6) -0.08828(13) 0.0465(5) Uani d 1 . .
H H21 0.889081 0.100122 -0.096147 0.056 Uiso calc 1 . .
C C22 0.9647(3) 0.15933(7) -0.09847(14) 0.0534(5) Uani d 1 . .
H H22A 1.081152 0.173431 -0.082773 0.064 Uiso calc 1 . .
H H22B 0.878139 0.165363 -0.161759 0.064 Uiso calc 1 . .
C C23 0.7097(4) 0.16848(9) -0.05411(19) 0.0713(7) Uani d 1 . .
H H23 0.616251 0.155454 -0.104575 0.086 Uiso calc 1 . .
C C24 0.8560(5) 0.19958(10) 0.0723(2) 0.0890(10) Uani d 1 . .
H H24 0.882190 0.212424 0.126934 0.107 Uiso calc 1 . .
C C25 0.9806(4) 0.19364(9) 0.04073(17) 0.0740(7) Uani d 1 . .
H H25 1.105748 0.201500 0.068588 0.089 Uiso calc 1 . .
C C26 1.0567(3) 0.09968(6) -0.15940(13) 0.0428(4) Uani d 1 . .
C C27 0.9243(3) 0.09325(6) -0.25002(13) 0.0430(4) Uani d 1 . .
C C28 0.9729(3) 0.08237(6) -0.31672(14) 0.0468(5) Uani d 1 . .
H H28 0.881519 0.078497 -0.376879 0.056 Uiso calc 1 . .
C C29 1.1606(3) 0.07737(7) -0.29179(15) 0.0499(5) Uani d 1 . .
C C30 1.2967(3) 0.08266(8) -0.20273(15) 0.0566(6) Uani d 1 . .
H H30 1.422457 0.078656 -0.186609 0.068 Uiso calc 1 . .
C C31 1.2443(3) 0.09399(7) -0.13746(15) 0.0526(5) Uani d 1 . .
H H31 1.336487 0.097905 -0.077492 0.063 Uiso calc 1 . .
C C32 1.1574(3) 0.06946(6) 0.03767(14) 0.0492(5) Uani d 1 . .
H H32A 1.182458 0.050138 0.000794 0.059 Uiso calc 1 . .
H H32B 1.039489 0.062406 0.036366 0.059 Uiso calc 1 . .
C C33 1.3141(3) 0.06876(6) 0.13486(14) 0.0473(5) Uani d 1 . .
C C34 1.3572(3) 0.03368(7) 0.18546(15) 0.0549(5) Uani d 1 . .
C C35 1.4993(4) 0.03144(9) 0.27474(17) 0.0697(7) Uani d 1 . .
H H35 1.525958 0.007487 0.307428 0.084 Uiso calc 1 . .
C C36 1.5993(3) 0.06587(9) 0.31331(16) 0.0682(7) Uani d 1 . .
C C37 1.5612(3) 0.10123(9) 0.26620(16) 0.0681(7) Uani d 1 . .
H H37 1.630056 0.124227 0.293744 0.082 Uiso calc 1 . .
C C38 1.4183(3) 0.10250(7) 0.17668(16) 0.0585(6) Uani d 1 . .
H H38 1.392399 0.126545 0.144359 0.070 Uiso calc 1 . .
H H3A 0.434(7) 0.2015(16) 0.1051(14) 0.20(2) Uiso d 1 . .
H H3B 0.468(5) 0.1927(12) 0.036(3) 0.155(18) 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 . . 114.17(16) ?
C21 O2 C32 . . 114.50(15) ?
H3A O3 H3B . . 98(4) ?
C3 N1 C5 . . 106.3(2) ?
C3 N1 C2 . . 127.1(2) ?
C5 N1 C2 . . 126.5(2) ?
C3 N2 C4 . . 104.3(2) ?
C23 N3 C25 . . 106.7(2) ?
C23 N3 C22 . . 126.8(2) ?
C25 N3 C22 . . 126.5(2) ?
C23 N4 C24 . . 105.3(2) ?
O1 C1 C6 . . 112.19(17) ?
O1 C1 C2 . . 105.75(17) ?
C6 C1 C2 . . 110.18(17) ?
O1 C1 H1 . . 109.5 ?
C6 C1 H1 . . 109.5 ?
C2 C1 H1 . . 109.5 ?
N1 C2 C1 . . 112.14(18) ?
N1 C2 H2A . . 109.2 ?
C1 C2 H2A . . 109.2 ?
N1 C2 H2B . . 109.2 ?
C1 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
N2 C3 N1 . . 112.5(3) ?
N2 C3 H3 . . 123.8 ?
N1 C3 H3 . . 123.8 ?
C5 C4 N2 . . 111.2(3) ?
C5 C4 H4 . . 124.4 ?
N2 C4 H4 . . 124.4 ?
C4 C5 N1 . . 105.8(3) ?
C4 C5 H5 . . 127.1 ?
N1 C5 H5 . . 127.1 ?
C7 C6 C11 . . 116.89(19) ?
C7 C6 C1 . . 121.48(17) ?
C11 C6 C1 . . 121.61(18) ?
C8 C7 C6 . . 122.76(18) ?
C8 C7 Cl1 . . 117.07(15) ?
C6 C7 Cl1 . . 120.17(15) ?
C7 C8 C9 . . 118.28(19) ?
C7 C8 H8 . . 120.9 ?
C9 C8 H8 . . 120.9 ?
C10 C9 C8 . . 121.2(2) ?
C10 C9 Cl2 . . 120.16(16) ?
C8 C9 Cl2 . . 118.63(16) ?
C11 C10 C9 . . 119.07(19) ?
C11 C10 H10 . . 120.5 ?
C9 C10 H10 . . 120.5 ?
C10 C11 C6 . . 121.8(2) ?
C10 C11 H11 . . 119.1 ?
C6 C11 H11 . . 119.1 ?
O1 C12 C13 . . 108.36(19) ?
O1 C12 H12A . . 110.0 ?
C13 C12 H12A . . 110.0 ?
O1 C12 H12B . . 110.0 ?
C13 C12 H12B . . 110.0 ?
H12A C12 H12B . . 108.4 ?
C18 C13 C14 . . 116.9(2) ?
C18 C13 C12 . . 122.2(2) ?
C14 C13 C12 . . 120.9(2) ?
C15 C14 C13 . . 122.0(2) ?
C15 C14 Cl3 . . 118.8(2) ?
C13 C14 Cl3 . . 119.2(2) ?
C16 C15 C14 . . 118.8(2) ?
C16 C15 H15 . . 120.6 ?
C14 C15 H15 . . 120.6 ?
C17 C16 C15 . . 121.5(2) ?
C17 C16 Cl4 . . 119.3(2) ?
C15 C16 Cl4 . . 119.2(2) ?
C16 C17 C18 . . 118.8(3) ?
C16 C17 H17 . . 120.6 ?
C18 C17 H17 . . 120.6 ?
C13 C18 C17 . . 122.1(2) ?
C13 C18 H18 . . 119.0 ?
C17 C18 H18 . . 119.0 ?
O2 C21 C26 . . 112.89(16) ?
O2 C21 C22 . . 105.38(17) ?
C26 C21 C22 . . 110.12(16) ?
O2 C21 H21 . . 109.5 ?
C26 C21 H21 . . 109.5 ?
C22 C21 H21 . . 109.5 ?
N3 C22 C21 . . 112.10(18) ?
N3 C22 H22A . . 109.2 ?
C21 C22 H22A . . 109.2 ?
N3 C22 H22B . . 109.2 ?
C21 C22 H22B . . 109.2 ?
H22A C22 H22B . . 107.9 ?
N4 C23 N3 . . 111.6(3) ?
N4 C23 H23 . . 124.2 ?
N3 C23 H23 . . 124.2 ?
C25 C24 N4 . . 110.1(3) ?
C25 C24 H24 . . 125.0 ?
N4 C24 H24 . . 125.0 ?
C24 C25 N3 . . 106.2(3) ?
C24 C25 H25 . . 126.9 ?
N3 C25 H25 . . 126.9 ?
C27 C26 C31 . . 116.89(18) ?
C27 C26 C21 . . 122.09(17) ?
C31 C26 C21 . . 120.94(18) ?
C28 C27 C26 . . 122.68(17) ?
C28 C27 Cl5 . . 116.84(15) ?
C26 C27 Cl5 . . 120.47(15) ?
C29 C28 C27 . . 118.29(19) ?
C29 C28 H28 . . 120.9 ?
C27 C28 H28 . . 120.9 ?
C30 C29 C28 . . 121.2(2) ?
C30 C29 Cl6 . . 120.45(16) ?
C28 C29 Cl6 . . 118.32(16) ?
C29 C30 C31 . . 119.31(19) ?
C29 C30 H30 . . 120.3 ?
C31 C30 H30 . . 120.3 ?
C30 C31 C26 . . 121.59(19) ?
C30 C31 H31 . . 119.2 ?
C26 C31 H31 . . 119.2 ?
O2 C32 C33 . . 108.14(17) ?
O2 C32 H32A . . 110.1 ?
C33 C32 H32A . . 110.1 ?
O2 C32 H32B . . 110.1 ?
C33 C32 H32B . . 110.1 ?
H32A C32 H32B . . 108.4 ?
C38 C33 C34 . . 117.5(2) ?
C38 C33 C32 . . 122.14(19) ?
C34 C33 C32 . . 120.4(2) ?
C33 C34 C35 . . 122.7(2) ?
C33 C34 Cl7 . . 119.16(17) ?
C35 C34 Cl7 . . 118.17(19) ?
C36 C35 C34 . . 117.6(2) ?
C36 C35 H35 . . 121.2 ?
C34 C35 H35 . . 121.2 ?
C37 C36 C35 . . 121.7(2) ?
C37 C36 Cl8 . . 119.3(2) ?
C35 C36 Cl8 . . 118.9(2) ?
C36 C37 C38 . . 119.3(3) ?
C36 C37 H37 . . 120.4 ?
C38 C37 H37 . . 120.4 ?
C33 C38 C37 . . 121.2(2) ?
C33 C38 H38 . . 119.4 ?
C37 C38 H38 . . 119.4 ?
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 . 1.7426(19) ?
Cl2 C9 . 1.739(2) ?
Cl3 C14 . 1.743(3) ?
Cl4 C16 . 1.744(3) ?
Cl5 C27 . 1.7455(19) ?
Cl6 C29 . 1.741(2) ?
Cl7 C34 . 1.743(2) ?
Cl8 C36 . 1.746(2) ?
O1 C1 . 1.419(2) ?
O1 C12 . 1.425(3) ?
O2 C21 . 1.417(2) ?
O2 C32 . 1.420(2) ?
O3 H3A . 0.874(19) ?
O3 H3B . 0.870(19) ?
N1 C3 . 1.344(3) ?
N1 C5 . 1.364(3) ?
N1 C2 . 1.455(3) ?
N2 C3 . 1.312(3) ?
N2 C4 . 1.355(4) ?
N3 C23 . 1.344(3) ?
N3 C25 . 1.366(3) ?
N3 C22 . 1.456(3) ?
N4 C23 . 1.312(3) ?
N4 C24 . 1.365(4) ?
C1 C6 . 1.522(3) ?
C1 C2 . 1.529(3) ?
C1 H1 . 0.9800 ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 H3 . 0.9300 ?
C4 C5 . 1.348(4) ?
C4 H4 . 0.9300 ?
C5 H5 . 0.9300 ?
C6 C7 . 1.390(3) ?
C6 C11 . 1.392(3) ?
C7 C8 . 1.378(3) ?
C8 C9 . 1.381(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.380(3) ?
C10 C11 . 1.380(3) ?
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 C13 . 1.503(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C18 . 1.379(3) ?
C13 C14 . 1.389(3) ?
C14 C15 . 1.385(4) ?
C15 C16 . 1.367(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.362(4) ?
C17 C18 . 1.388(3) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
C21 C26 . 1.515(3) ?
C21 C22 . 1.523(3) ?
C21 H21 . 0.9800 ?
C22 H22A . 0.9700 ?
C22 H22B . 0.9700 ?
C23 H23 . 0.9300 ?
C24 C25 . 1.346(4) ?
C24 H24 . 0.9300 ?
C25 H25 . 0.9300 ?
C26 C27 . 1.392(3) ?
C26 C31 . 1.394(3) ?
C27 C28 . 1.381(3) ?
C28 C29 . 1.380(3) ?
C28 H28 . 0.9300 ?
C29 C30 . 1.377(3) ?
C30 C31 . 1.383(3) ?
C30 H30 . 0.9300 ?
C31 H31 . 0.9300 ?
C32 C33 . 1.511(3) ?
C32 H32A . 0.9700 ?
C32 H32B . 0.9700 ?
C33 C38 . 1.378(3) ?
C33 C34 . 1.383(3) ?
C34 C35 . 1.385(3) ?
C35 C36 . 1.374(4) ?
C35 H35 . 0.9300 ?
C36 C37 . 1.364(4) ?
C37 C38 . 1.389(3) ?
C37 H37 . 0.9300 ?
C38 H38 . 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
O3 H3A N2 . 0.874(19) 2.02(2) 2.878(4) 168(5) yes
O3 H3B N4 . 0.870(19) 1.99(2) 2.823(3) 160(4) yes
C2 H2B O3 4_566 0.97 2.59 3.354(3) 136.0 yes
C22 H22A O3 1_655 0.97 2.60 3.451(3) 146.8 yes
C25 H25 O3 1_655 0.93 2.44 3.236(4) 143.1 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 C6 . . . . -78.4(2) ?
C12 O1 C1 C2 . . . . 161.48(18) ?
C3 N1 C2 C1 . . . . 82.6(3) ?
C5 N1 C2 C1 . . . . -94.6(3) ?
O1 C1 C2 N1 . . . . -70.9(2) ?
C6 C1 C2 N1 . . . . 167.66(17) ?
C4 N2 C3 N1 . . . . 0.3(3) ?
C5 N1 C3 N2 . . . . -0.3(3) ?
C2 N1 C3 N2 . . . . -178.0(2) ?
C3 N2 C4 C5 . . . . -0.1(3) ?
N2 C4 C5 N1 . . . . 0.0(3) ?
C3 N1 C5 C4 . . . . 0.2(3) ?
C2 N1 C5 C4 . . . . 177.9(2) ?
O1 C1 C6 C7 . . . . 164.04(18) ?
C2 C1 C6 C7 . . . . -78.4(2) ?
O1 C1 C6 C11 . . . . -17.5(3) ?
C2 C1 C6 C11 . . . . 100.0(2) ?
C11 C6 C7 C8 . . . . 0.6(3) ?
C1 C6 C7 C8 . . . . 179.13(19) ?
C11 C6 C7 Cl1 . . . . 179.98(16) ?
C1 C6 C7 Cl1 . . . . -1.5(3) ?
C6 C7 C8 C9 . . . . 0.0(3) ?
Cl1 C7 C8 C9 . . . . -179.43(16) ?
C7 C8 C9 C10 . . . . -0.1(3) ?
C7 C8 C9 Cl2 . . . . 179.84(16) ?
C8 C9 C10 C11 . . . . -0.4(3) ?
Cl2 C9 C10 C11 . . . . 179.69(18) ?
C9 C10 C11 C6 . . . . 1.0(4) ?
C7 C6 C11 C10 . . . . -1.1(3) ?
C1 C6 C11 C10 . . . . -179.6(2) ?
C1 O1 C12 C13 . . . . 178.72(17) ?
O1 C12 C13 C18 . . . . 4.8(3) ?
O1 C12 C13 C14 . . . . -175.3(2) ?
C18 C13 C14 C15 . . . . -0.2(4) ?
C12 C13 C14 C15 . . . . 179.9(2) ?
C18 C13 C14 Cl3 . . . . 179.69(18) ?
C12 C13 C14 Cl3 . . . . -0.2(3) ?
C13 C14 C15 C16 . . . . 0.5(4) ?
Cl3 C14 C15 C16 . . . . -179.4(2) ?
C14 C15 C16 C17 . . . . -0.6(4) ?
C14 C15 C16 Cl4 . . . . 179.4(2) ?
C15 C16 C17 C18 . . . . 0.4(4) ?
Cl4 C16 C17 C18 . . . . -179.6(2) ?
C14 C13 C18 C17 . . . . 0.0(4) ?
C12 C13 C18 C17 . . . . 179.8(2) ?
C16 C17 C18 C13 . . . . -0.1(4) ?
C32 O2 C21 C26 . . . . -81.7(2) ?
C32 O2 C21 C22 . . . . 158.12(17) ?
C23 N3 C22 C21 . . . . -74.8(3) ?
C25 N3 C22 C21 . . . . 101.9(3) ?
O2 C21 C22 N3 . . . . -66.2(2) ?
C26 C21 C22 N3 . . . . 171.81(17) ?
C24 N4 C23 N3 . . . . -0.7(3) ?
C25 N3 C23 N4 . . . . 0.5(3) ?
C22 N3 C23 N4 . . . . 177.8(2) ?
C23 N4 C24 C25 . . . . 0.6(4) ?
N4 C24 C25 N3 . . . . -0.3(3) ?
C23 N3 C25 C24 . . . . -0.1(3) ?
C22 N3 C25 C24 . . . . -177.4(2) ?
O2 C21 C26 C27 . . . . 164.41(18) ?
C22 C21 C26 C27 . . . . -78.1(2) ?
O2 C21 C26 C31 . . . . -18.8(3) ?
C22 C21 C26 C31 . . . . 98.6(2) ?
C31 C26 C27 C28 . . . . -1.0(3) ?
C21 C26 C27 C28 . . . . 175.89(19) ?
C31 C26 C27 Cl5 . . . . 178.38(16) ?
C21 C26 C27 Cl5 . . . . -4.7(3) ?
C26 C27 C28 C29 . . . . 0.6(3) ?
Cl5 C27 C28 C29 . . . . -178.84(16) ?
C27 C28 C29 C30 . . . . 0.6(3) ?
C27 C28 C29 Cl6 . . . . -179.99(16) ?
C28 C29 C30 C31 . . . . -1.3(4) ?
Cl6 C29 C30 C31 . . . . 179.30(18) ?
C29 C30 C31 C26 . . . . 0.9(4) ?
C27 C26 C31 C30 . . . . 0.3(3) ?
C21 C26 C31 C30 . . . . -176.7(2) ?
C21 O2 C32 C33 . . . . -178.74(16) ?
O2 C32 C33 C38 . . . . 1.2(3) ?
O2 C32 C33 C34 . . . . -179.16(19) ?
C38 C33 C34 C35 . . . . -0.3(3) ?
C32 C33 C34 C35 . . . . -180.0(2) ?
C38 C33 C34 Cl7 . . . . 179.97(17) ?
C32 C33 C34 Cl7 . . . . 0.3(3) ?
C33 C34 C35 C36 . . . . 0.2(4) ?
Cl7 C34 C35 C36 . . . . 179.88(19) ?
C34 C35 C36 C37 . . . . 0.2(4) ?
C34 C35 C36 Cl8 . . . . -178.92(18) ?
C35 C36 C37 C38 . . . . -0.4(4) ?
Cl8 C36 C37 C38 . . . . 178.69(19) ?
C34 C33 C38 C37 . . . . 0.1(3) ?
C32 C33 C38 C37 . . . . 179.7(2) ?
C36 C37 C38 C33 . . . . 0.3(4) ?

_cod_database_fobs_code 2022609
