#------------------------------------------------------------------------------
#$Date: 2025-06-26 05:34:20 +0300 (Thu, 26 Jun 2025) $
#$Revision: 300216 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/35/2023529.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_2023529
loop_
_publ_author_name
'Mohan Kumar, Thaluru M.'
'Bhavya, Papegowda'
'Bhaskar, Besagarahally L.'
'Shankara Prasad, Holehundi J.'
'Yathirajan, Hemmige S.'
'Parkin, Sean'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 1-[2-(2-chloroethoxy)ethyl]-2-methyl-4-nitro-1H-imidazole
;
_journal_coeditor_code           NX2027
_journal_issue                   7
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989025005493
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          'C8 H12 Cl N3 O3'
_chemical_formula_moiety         'C8 H12 Cl N3 O3'
_chemical_formula_sum            'C8 H12 Cl N3 O3'
_chemical_formula_weight         233.66
_chemical_name_systematic
;
1-[2-(2-Chloroethoxy)ethyl]-2-methyl-4-nitro-1H-imidazole
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-2019/3 and CIFFIX'
_cell_angle_alpha                98.662(2)
_cell_angle_beta                 93.164(2)
_cell_angle_gamma                103.444(2)
_cell_formula_units_Z            4
_cell_length_a                   8.5810(4)
_cell_length_b                   11.1448(7)
_cell_length_c                   11.5757(5)
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.71
_cell_volume                     1059.71(10)
_computing_cell_refinement
;
APEX5 (Bruker, 2023)
;
_computing_data_collection
;
APEX5 (Bruker, 2023)
;
_computing_data_reduction
;
APEX5 (Bruker, 2023)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2020) and
Overlay.py (Parkin, 2025)
;
_computing_publication_material
;
SHELX (Sheldrick, 2008) and publCIF (Westrip 2010)
;
_computing_structure_refinement
;
SHELXL2019/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector_area_resol_mean 7.41
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            34130
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.561
_diffrn_reflns_theta_min         1.906
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_description       'solvent-rounded block'
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.353
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4879
_refine_ls_number_restraints     416
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0306
_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)+(0.0258P)²+0.4798P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0758
_reflns_number_gt                4337
_reflns_number_total             4879
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            nx2027.cif
_cod_data_source_block           I
_cod_database_code               2023529
_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   0.917
_shelx_estimated_absorpt_t_max   0.956
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
O O2A 0.92119(11) 0.09620(9) 0.10635(8) 0.0291(2) Uani d 1 . .
O O3A 0.92893(11) 0.11525(10) 0.29564(8) 0.0349(2) Uani d 1 . .
N N1A 0.47096(11) 0.15624(9) 0.13212(8) 0.01687(19) Uani d 1 . .
N N2A 0.62164(11) 0.14669(9) 0.29175(8) 0.01833(19) Uani d 1 . .
N N3A 0.86024(12) 0.11372(10) 0.19955(9) 0.0218(2) Uani d 1 . .
C C1A 0.61200(13) 0.13743(10) 0.09384(10) 0.0187(2) Uani d 1 . .
H H1A 0.641682 0.129776 0.015705 0.022 Uiso calc 1 . .
C C2A 0.70087(13) 0.13209(10) 0.19353(10) 0.0178(2) Uani d 1 . .
C C3A 0.48135(13) 0.16128(10) 0.25182(9) 0.0173(2) Uani d 1 . .
C C4A 0.35045(15) 0.18143(12) 0.32518(11) 0.0245(2) Uani d 1 . .
H H4AA 0.344755 0.269030 0.332592 0.037 Uiso calc 1 . .
H H4AB 0.372346 0.161678 0.403229 0.037 Uiso calc 1 . .
H H4AC 0.247736 0.126885 0.288206 0.037 Uiso calc 1 . .
C C5A 0.3362(11) 0.1720(6) 0.0572(9) 0.0202(4) Uani d 0.726(4) A 1
H H5A1 0.237703 0.158758 0.099079 0.024 Uiso calc 0.726(4) A 1
H H5A2 0.316384 0.108581 -0.015167 0.024 Uiso calc 0.726(4) A 1
C C6A 0.3727(5) 0.3019(4) 0.0251(3) 0.0229(6) Uani d 0.726(4) A 1
H H6A1 0.475029 0.316384 -0.012149 0.027 Uiso calc 0.726(4) A 1
H H6A2 0.286365 0.306822 -0.033069 0.027 Uiso calc 0.726(4) A 1
O O1A 0.38532(18) 0.39806(13) 0.12420(15) 0.0220(4) Uani d 0.726(4) A 1
C C7A 0.2349(2) 0.41695(19) 0.15685(16) 0.0259(5) Uani d 0.726(4) A 1
H H7A1 0.180335 0.347938 0.196203 0.031 Uiso calc 0.726(4) A 1
H H7A2 0.165106 0.417948 0.086170 0.031 Uiso calc 0.726(4) A 1
C C8A 0.2632(3) 0.5393(2) 0.2385(2) 0.0274(5) Uani d 0.726(4) A 1
H H8A1 0.158339 0.558782 0.252617 0.033 Uiso calc 0.726(4) A 1
H H8A2 0.326692 0.606367 0.200905 0.033 Uiso calc 0.726(4) A 1
Cl Cl1A 0.36807(19) 0.53736(14) 0.37668(12) 0.0386(2) Uani d 0.726(4) A 1
C C5C 0.341(3) 0.1759(15) 0.054(2) 0.0202(4) Uani d 0.274(4) A 2
H H5C1 0.236152 0.137875 0.081366 0.024 Uiso calc 0.274(4) A 2
H H5C2 0.345245 0.132358 -0.026044 0.024 Uiso calc 0.274(4) A 2
C C6C 0.3512(15) 0.3136(10) 0.0509(8) 0.0217(15) Uani d 0.274(4) A 2
H H6C1 0.457012 0.354212 0.027037 0.026 Uiso calc 0.274(4) A 2
H H6C2 0.265792 0.322112 -0.006061 0.026 Uiso calc 0.274(4) A 2
O O1C 0.3310(6) 0.3704(3) 0.1662(4) 0.0233(9) Uani d 0.274(4) A 2
C C7C 0.3083(7) 0.4938(5) 0.1727(4) 0.0267(11) Uani d 0.274(4) A 2
H H7C1 0.225414 0.495346 0.110339 0.032 Uiso calc 0.274(4) A 2
H H7C2 0.410135 0.552217 0.161089 0.032 Uiso calc 0.274(4) A 2
C C8C 0.2564(7) 0.5327(6) 0.2901(5) 0.0242(12) Uani d 0.274(4) A 2
H H8C1 0.161515 0.468239 0.303757 0.029 Uiso calc 0.274(4) A 2
H H8C2 0.222764 0.611874 0.290270 0.029 Uiso calc 0.274(4) A 2
Cl Cl1C 0.4080(5) 0.5545(4) 0.4069(3) 0.0406(6) Uani d 0.274(4) A 2
O O2B 0.31302(10) 0.11153(8) 0.58764(7) 0.02304(18) Uani d 1 . .
O O3B 0.32527(10) 0.15036(9) 0.77777(7) 0.0271(2) Uani d 1 . .
N N1B 0.79607(11) 0.14491(9) 0.64445(8) 0.01650(19) Uani d 1 . .
N N2B 0.64632(11) 0.15332(9) 0.79508(8) 0.01790(19) Uani d 1 . .
N N3B 0.38786(11) 0.13284(9) 0.68559(8) 0.01845(19) Uani d 1 . .
C C1B 0.64369(13) 0.13249(10) 0.59632(9) 0.0163(2) Uani d 1 . .
H H1B 0.607010 0.122179 0.515661 0.020 Uiso calc 1 . .
C C2B 0.55580(13) 0.13829(10) 0.69080(9) 0.0160(2) Uani d 1 . .
C C3B 0.79288(13) 0.15741(10) 0.76422(10) 0.0177(2) Uani d 1 . .
C C4B 0.93855(15) 0.17517(13) 0.84634(11) 0.0267(3) Uani d 1 . .
H H4BA 0.982002 0.100900 0.832161 0.040 Uiso calc 1 . .
H H4BB 0.910085 0.187629 0.927358 0.040 Uiso calc 1 . .
H H4BC 1.019765 0.248707 0.833718 0.040 Uiso calc 1 . .
C C5B 0.9357(11) 0.1542(6) 0.5756(11) 0.0193(8) Uani d 0.638(4) B 1
H H5B1 0.910198 0.085226 0.507494 0.023 Uiso calc 0.638(4) B 1
H H5B2 1.027707 0.143070 0.624673 0.023 Uiso calc 0.638(4) B 1
C C6B 0.9854(6) 0.2777(4) 0.5312(4) 0.0233(8) Uani d 0.638(4) B 1
H H6B1 1.073322 0.274029 0.479890 0.028 Uiso calc 0.638(4) B 1
H H6B2 0.892957 0.289801 0.483202 0.028 Uiso calc 0.638(4) B 1
O O1B 1.03761(19) 0.38096(16) 0.62241(18) 0.0281(5) Uani d 0.638(4) B 1
C C7B 1.2020(3) 0.4077(3) 0.6584(2) 0.0312(6) Uani d 0.638(4) B 1
H H7B1 1.263984 0.406201 0.588835 0.037 Uiso calc 0.638(4) B 1
H H7B2 1.223886 0.343287 0.702940 0.037 Uiso calc 0.638(4) B 1
C C8B 1.2537(6) 0.5338(5) 0.7340(4) 0.0293(9) Uani d 0.638(4) B 1
H H8B1 1.220284 0.596075 0.691951 0.035 Uiso calc 0.638(4) B 1
H H8B2 1.372571 0.557584 0.747663 0.035 Uiso calc 0.638(4) B 1
Cl Cl1B 1.1692(2) 0.5392(2) 0.87550(19) 0.0367(3) Uani d 0.638(4) B 1
C C5D 0.937(2) 0.1368(12) 0.580(2) 0.0193(8) Uani d 0.362(4) B 2
H H5D1 0.904352 0.077503 0.504957 0.023 Uiso calc 0.362(4) B 2
H H5D2 1.015649 0.106792 0.627016 0.023 Uiso calc 0.362(4) B 2
C C6D 1.0118(11) 0.2649(8) 0.5563(6) 0.0236(13) Uani d 0.362(4) B 2
H H6D1 1.098517 0.261355 0.503766 0.028 Uiso calc 0.362(4) B 2
H H6D2 0.929752 0.298498 0.517142 0.028 Uiso calc 0.362(4) B 2
O O1D 1.0767(3) 0.3445(2) 0.6658(2) 0.0178(6) Uani d 0.362(4) B 2
C C7D 1.1612(5) 0.4697(4) 0.6524(3) 0.0271(9) Uani d 0.362(4) B 2
H H7D1 1.083704 0.520077 0.636796 0.033 Uiso calc 0.362(4) B 2
H H7D2 1.229548 0.466398 0.586434 0.033 Uiso calc 0.362(4) B 2
C C8D 1.2633(12) 0.5263(9) 0.7665(6) 0.0341(17) Uani d 0.362(4) B 2
H H8D1 1.338712 0.605825 0.758187 0.041 Uiso calc 0.362(4) B 2
H H8D2 1.327000 0.468248 0.788573 0.041 Uiso calc 0.362(4) B 2
Cl Cl1D 1.1350(4) 0.5536(4) 0.8748(4) 0.0367(3) Uani d 0.362(4) 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 0.0033 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
C1A N1A C3A . . 107.79(9) ?
C1A N1A C5A . . 125.0(5) ?
C3A N1A C5A . . 127.2(5) ?
C1A N1A C5C . . 123.1(13) ?
C3A N1A C5C . . 129.0(13) ?
C3A N2A C2A . . 103.88(9) ?
O3A N3A O2A . . 123.38(10) ?
O3A N3A C2A . . 119.06(10) ?
O2A N3A C2A . . 117.55(9) ?
N1A C1A C2A . . 104.08(9) ?
N1A C1A H1A . . 128.0 ?
C2A C1A H1A . . 128.0 ?
C1A C2A N2A . . 112.85(10) ?
C1A C2A N3A . . 125.68(10) ?
N2A C2A N3A . . 121.47(10) ?
N2A C3A N1A . . 111.39(9) ?
N2A C3A C4A . . 125.06(10) ?
N1A C3A C4A . . 123.55(10) ?
C3A C4A H4AA . . 109.5 ?
C3A C4A H4AB . . 109.5 ?
H4AA C4A H4AB . . 109.5 ?
C3A C4A H4AC . . 109.5 ?
H4AA C4A H4AC . . 109.5 ?
H4AB C4A H4AC . . 109.5 ?
N1A C5A C6A . . 110.6(5) ?
N1A C5A H5A1 . . 109.5 ?
C6A C5A H5A1 . . 109.5 ?
N1A C5A H5A2 . . 109.5 ?
C6A C5A H5A2 . . 109.5 ?
H5A1 C5A H5A2 . . 108.1 ?
O1A C6A C5A . . 112.8(5) ?
O1A C6A H6A1 . . 109.0 ?
C5A C6A H6A1 . . 109.0 ?
O1A C6A H6A2 . . 109.0 ?
C5A C6A H6A2 . . 109.0 ?
H6A1 C6A H6A2 . . 107.8 ?
C7A O1A C6A . . 113.8(2) ?
O1A C7A C8A . . 108.77(17) ?
O1A C7A H7A1 . . 109.9 ?
C8A C7A H7A1 . . 109.9 ?
O1A C7A H7A2 . . 109.9 ?
C8A C7A H7A2 . . 109.9 ?
H7A1 C7A H7A2 . . 108.3 ?
C7A C8A Cl1A . . 112.35(16) ?
C7A C8A H8A1 . . 109.1 ?
Cl1A C8A H8A1 . . 109.1 ?
C7A C8A H8A2 . . 109.1 ?
Cl1A C8A H8A2 . . 109.1 ?
H8A1 C8A H8A2 . . 107.9 ?
N1A C5C C6C . . 113.1(12) ?
N1A C5C H5C1 . . 109.0 ?
C6C C5C H5C1 . . 109.0 ?
N1A C5C H5C2 . . 109.0 ?
C6C C5C H5C2 . . 109.0 ?
H5C1 C5C H5C2 . . 107.8 ?
O1C C6C C5C . . 107.2(13) ?
O1C C6C H6C1 . . 110.3 ?
C5C C6C H6C1 . . 110.3 ?
O1C C6C H6C2 . . 110.3 ?
C5C C6C H6C2 . . 110.3 ?
H6C1 C6C H6C2 . . 108.5 ?
C7C O1C C6C . . 113.8(6) ?
O1C C7C C8C . . 108.6(5) ?
O1C C7C H7C1 . . 110.0 ?
C8C C7C H7C1 . . 110.0 ?
O1C C7C H7C2 . . 110.0 ?
C8C C7C H7C2 . . 110.0 ?
H7C1 C7C H7C2 . . 108.3 ?
C7C C8C Cl1C . . 113.6(4) ?
C7C C8C H8C1 . . 108.8 ?
Cl1C C8C H8C1 . . 108.8 ?
C7C C8C H8C2 . . 108.8 ?
Cl1C C8C H8C2 . . 108.8 ?
H8C1 C8C H8C2 . . 107.7 ?
C1B N1B C3B . . 107.89(9) ?
C1B N1B C5B . . 123.2(5) ?
C3B N1B C5B . . 128.6(5) ?
C1B N1B C5D . . 126.2(10) ?
C3B N1B C5D . . 125.7(10) ?
C3B N2B C2B . . 103.77(9) ?
O3B N3B O2B . . 123.41(9) ?
O3B N3B C2B . . 118.99(9) ?
O2B N3B C2B . . 117.59(9) ?
N1B C1B C2B . . 103.94(9) ?
N1B C1B H1B . . 128.0 ?
C2B C1B H1B . . 128.0 ?
C1B C2B N2B . . 112.97(9) ?
C1B C2B N3B . . 125.27(10) ?
N2B C2B N3B . . 121.75(9) ?
N2B C3B N1B . . 111.43(9) ?
N2B C3B C4B . . 125.39(10) ?
N1B C3B C4B . . 123.18(10) ?
C3B C4B H4BA . . 109.5 ?
C3B C4B H4BB . . 109.5 ?
H4BA C4B H4BB . . 109.5 ?
C3B C4B H4BC . . 109.5 ?
H4BA C4B H4BC . . 109.5 ?
H4BB C4B H4BC . . 109.5 ?
N1B C5B C6B . . 113.7(5) ?
N1B C5B H5B1 . . 108.8 ?
C6B C5B H5B1 . . 108.8 ?
N1B C5B H5B2 . . 108.8 ?
C6B C5B H5B2 . . 108.8 ?
H5B1 C5B H5B2 . . 107.7 ?
O1B C6B C5B . . 113.0(5) ?
O1B C6B H6B1 . . 109.0 ?
C5B C6B H6B1 . . 109.0 ?
O1B C6B H6B2 . . 109.0 ?
C5B C6B H6B2 . . 109.0 ?
H6B1 C6B H6B2 . . 107.8 ?
C7B O1B C6B . . 113.8(2) ?
O1B C7B C8B . . 109.9(3) ?
O1B C7B H7B1 . . 109.7 ?
C8B C7B H7B1 . . 109.7 ?
O1B C7B H7B2 . . 109.7 ?
C8B C7B H7B2 . . 109.7 ?
H7B1 C7B H7B2 . . 108.2 ?
C7B C8B Cl1B . . 113.0(3) ?
C7B C8B H8B1 . . 109.0 ?
Cl1B C8B H8B1 . . 109.0 ?
C7B C8B H8B2 . . 109.0 ?
Cl1B C8B H8B2 . . 109.0 ?
H8B1 C8B H8B2 . . 107.8 ?
N1B C5D C6D . . 107.5(9) ?
N1B C5D H5D1 . . 110.2 ?
C6D C5D H5D1 . . 110.2 ?
N1B C5D H5D2 . . 110.2 ?
C6D C5D H5D2 . . 110.2 ?
H5D1 C5D H5D2 . . 108.5 ?
O1D C6D C5D . . 108.7(9) ?
O1D C6D H6D1 . . 109.9 ?
C5D C6D H6D1 . . 109.9 ?
O1D C6D H6D2 . . 109.9 ?
C5D C6D H6D2 . . 109.9 ?
H6D1 C6D H6D2 . . 108.3 ?
C6D O1D C7D . . 113.3(4) ?
O1D C7D C8D . . 106.2(5) ?
O1D C7D H7D1 . . 110.5 ?
C8D C7D H7D1 . . 110.5 ?
O1D C7D H7D2 . . 110.5 ?
C8D C7D H7D2 . . 110.5 ?
H7D1 C7D H7D2 . . 108.7 ?
C7D C8D Cl1D . . 108.1(6) ?
C7D C8D H8D1 . . 110.1 ?
Cl1D C8D H8D1 . . 110.1 ?
C7D C8D H8D2 . . 110.1 ?
Cl1D C8D H8D2 . . 110.1 ?
H8D1 C8D H8D2 . . 108.4 ?
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
O2A N3A . 1.2336(13) ?
O3A N3A . 1.2257(13) ?
N1A C1A . 1.3617(14) ?
N1A C3A . 1.3753(14) ?
N1A C5A . 1.466(5) ?
N1A C5C . 1.470(14) ?
N2A C3A . 1.3197(14) ?
N2A C2A . 1.3648(14) ?
N3A C2A . 1.4286(14) ?
C1A C2A . 1.3643(16) ?
C1A H1A . 0.9500 ?
C3A C4A . 1.4827(15) ?
C4A H4AA . 0.9800 ?
C4A H4AB . 0.9800 ?
C4A H4AC . 0.9800 ?
C5A C6A . 1.516(6) ?
C5A H5A1 . 0.9900 ?
C5A H5A2 . 0.9900 ?
C6A O1A . 1.427(3) ?
C6A H6A1 . 0.9900 ?
C6A H6A2 . 0.9900 ?
O1A C7A . 1.417(2) ?
C7A C8A . 1.498(3) ?
C7A H7A1 . 0.9900 ?
C7A H7A2 . 0.9900 ?
C8A Cl1A . 1.797(3) ?
C8A H8A1 . 0.9900 ?
C8A H8A2 . 0.9900 ?
C5C C6C . 1.523(13) ?
C5C H5C1 . 0.9900 ?
C5C H5C2 . 0.9900 ?
C6C O1C . 1.426(8) ?
C6C H6C1 . 0.9900 ?
C6C H6C2 . 0.9900 ?
O1C C7C . 1.424(6) ?
C7C C8C . 1.488(7) ?
C7C H7C1 . 0.9900 ?
C7C H7C2 . 0.9900 ?
C8C Cl1C . 1.772(6) ?
C8C H8C1 . 0.9900 ?
C8C H8C2 . 0.9900 ?
O2B N3B . 1.2337(12) ?
O3B N3B . 1.2306(12) ?
N1B C1B . 1.3607(14) ?
N1B C3B . 1.3749(14) ?
N1B C5B . 1.468(7) ?
N1B C5D . 1.474(12) ?
N2B C3B . 1.3188(14) ?
N2B C2B . 1.3652(14) ?
N3B C2B . 1.4257(14) ?
C1B C2B . 1.3643(15) ?
C1B H1B . 0.9500 ?
C3B C4B . 1.4840(15) ?
C4B H4BA . 0.9800 ?
C4B H4BB . 0.9800 ?
C4B H4BC . 0.9800 ?
C5B C6B . 1.518(6) ?
C5B H5B1 . 0.9900 ?
C5B H5B2 . 0.9900 ?
C6B O1B . 1.408(4) ?
C6B H6B1 . 0.9900 ?
C6B H6B2 . 0.9900 ?
O1B C7B . 1.398(3) ?
C7B C8B . 1.495(5) ?
C7B H7B1 . 0.9900 ?
C7B H7B2 . 0.9900 ?
C8B Cl1B . 1.826(5) ?
C8B H8B1 . 0.9900 ?
C8B H8B2 . 0.9900 ?
C5D C6D . 1.494(11) ?
C5D H5D1 . 0.9900 ?
C5D H5D2 . 0.9900 ?
C6D O1D . 1.435(7) ?
C6D H6D1 . 0.9900 ?
C6D H6D2 . 0.9900 ?
O1D C7D . 1.450(4) ?
C7D C8D . 1.508(8) ?
C7D H7D1 . 0.9900 ?
C7D H7D2 . 0.9900 ?
C8D Cl1D . 1.752(9) ?
C8D H8D1 . 0.9900 ?
C8D H8D2 . 0.9900 ?
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
C1A H1A N2B 1_554 0.95 2.61 3.5144(15) 159.7 yes
C4A H4AA Cl1A . 0.98 2.91 3.888(2) 172.1 yes
C4A H4AA O1C . 0.98 2.39 3.024(4) 122.2 yes
C4A H4AB O2B . 0.98 2.34 3.2626(14) 156.6 yes
C5A H5A1 O2A 1_455 0.99 2.65 3.562(10) 153.0 yes
C5A H5A2 O3B 1_554 0.99 2.51 3.202(10) 126.6 yes
C7A H7A2 Cl1B 1_454 0.99 2.96 3.778(3) 140.8 yes
C8A H8A1 O1B 2_666 0.99 2.42 3.338(3) 153.4 yes
C8A H8A1 Cl1B 2_666 0.99 2.99 3.725(3) 132.3 yes
C8A H8A2 N2B 2_666 0.99 2.63 3.419(3) 137.1 yes
C5C H5C2 O3B 1_554 0.99 2.31 3.16(3) 143.9 yes
C1B H1B N2A . 0.95 2.65 3.5495(14) 157.4 yes
C4B H4BB O2A 1_556 0.98 2.45 3.2622(15) 140.1 yes
C4B H4BC O1D . 0.98 2.38 3.124(3) 132.6 yes
C5B H5B1 O3A . 0.99 2.53 3.199(12) 124.4 yes
C5B H5B1 O2B 2_656 0.99 2.60 3.439(10) 142.1 yes
C5B H5B2 O2B 1_655 0.99 2.60 3.379(10) 135.4 yes
C8B H8B2 O1A 2_766 0.99 2.39 3.292(5) 150.8 yes
C5D H5D1 O3A . 0.99 2.53 3.26(2) 129.8 yes
C5D H5D1 O2B 2_656 0.99 2.52 3.345(19) 141.0 yes
C5D H5D2 O2B 1_655 0.99 2.61 3.297(17) 126.9 yes
C7D H7D2 Cl1C 1_655 0.99 2.81 3.742(6) 157.1 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
C3A N1A C1A C2A . . . . -0.01(12) ?
C5A N1A C1A C2A . . . . 178.2(3) ?
C5C N1A C1A C2A . . . . 176.0(8) ?
N1A C1A C2A N2A . . . . 0.01(13) ?
N1A C1A C2A N3A . . . . -179.85(10) ?
C3A N2A C2A C1A . . . . 0.00(13) ?
C3A N2A C2A N3A . . . . 179.87(10) ?
O3A N3A C2A C1A . . . . 177.43(11) ?
O2A N3A C2A C1A . . . . -3.03(17) ?
O3A N3A C2A N2A . . . . -2.42(17) ?
O2A N3A C2A N2A . . . . 177.12(10) ?
C2A N2A C3A N1A . . . . -0.01(12) ?
C2A N2A C3A C4A . . . . -179.66(11) ?
C1A N1A C3A N2A . . . . 0.02(13) ?
C5A N1A C3A N2A . . . . -178.2(3) ?
C5C N1A C3A N2A . . . . -175.7(9) ?
C1A N1A C3A C4A . . . . 179.67(10) ?
C5A N1A C3A C4A . . . . 1.5(4) ?
C5C N1A C3A C4A . . . . 3.9(9) ?
C1A N1A C5A C6A . . . . -76.1(7) ?
C3A N1A C5A C6A . . . . 101.8(7) ?
N1A C5A C6A O1A . . . . -65.6(8) ?
C5A C6A O1A C7A . . . . -81.8(5) ?
C6A O1A C7A C8A . . . . -165.1(2) ?
O1A C7A C8A Cl1A . . . . -66.8(2) ?
C1A N1A C5C C6C . . . . -92.7(19) ?
C3A N1A C5C C6C . . . . 82(2) ?
N1A C5C C6C O1C . . . . -64(2) ?
C5C C6C O1C C7C . . . . -169.2(10) ?
C6C O1C C7C C8C . . . . 168.8(6) ?
O1C C7C C8C Cl1C . . . . 68.1(6) ?
C3B N1B C1B C2B . . . . 0.02(12) ?
C5B N1B C1B C2B . . . . -174.9(3) ?
C5D N1B C1B C2B . . . . 175.7(6) ?
N1B C1B C2B N2B . . . . -0.18(12) ?
N1B C1B C2B N3B . . . . 178.29(10) ?
C3B N2B C2B C1B . . . . 0.27(12) ?
C3B N2B C2B N3B . . . . -178.27(10) ?
O3B N3B C2B C1B . . . . -173.51(11) ?
O2B N3B C2B C1B . . . . 5.93(16) ?
O3B N3B C2B N2B . . . . 4.84(16) ?
O2B N3B C2B N2B . . . . -175.72(10) ?
C2B N2B C3B N1B . . . . -0.25(12) ?
C2B N2B C3B C4B . . . . 178.83(11) ?
C1B N1B C3B N2B . . . . 0.15(13) ?
C5B N1B C3B N2B . . . . 174.7(3) ?
C5D N1B C3B N2B . . . . -175.6(6) ?
C1B N1B C3B C4B . . . . -178.95(11) ?
C5B N1B C3B C4B . . . . -4.4(4) ?
C5D N1B C3B C4B . . . . 5.3(6) ?
C1B N1B C5B C6B . . . . 71.3(8) ?
C3B N1B C5B C6B . . . . -102.5(8) ?
N1B C5B C6B O1B . . . . 63.8(10) ?
C5B C6B O1B C7B . . . . 88.4(5) ?
C6B O1B C7B C8B . . . . 166.9(3) ?
O1B C7B C8B Cl1B . . . . 68.2(4) ?
C1B N1B C5D C6D . . . . 88.2(13) ?
C3B N1B C5D C6D . . . . -96.8(14) ?
N1B C5D C6D O1D . . . . 67.1(16) ?
C5D C6D O1D C7D . . . . 176.3(8) ?
C6D O1D C7D C8D . . . . -162.6(6) ?
O1D C7D C8D Cl1D . . . . -69.9(7) ?
