#------------------------------------------------------------------------------
#$Date: 2020-10-10 08:30:15 +0300 (Sat, 10 Oct 2020) $
#$Revision: 258299 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/36/2243621.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_2243621
loop_
_publ_author_name
'Meesakul, Pornphimol'
'Richardson, Christopher'
'Laphookhieo, Surat'
'Pyne, Stephen G.'
_publ_section_title
;
 Synthesis and crystal structure of (+-)-Goniotamirenone C
;
_journal_coeditor_code           VM2241
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1728
_journal_page_last               1731
_journal_paper_doi               10.1107/S2056989020013298
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C13 H11 Cl O3'
_chemical_formula_moiety         'C13 H11 Cl O3'
_chemical_formula_sum            'C13 H11 Cl O3'
_chemical_formula_weight         250.67
_chemical_melting_point_gt       394
_chemical_melting_point_lt       396
_chemical_name_common            'Goniotamirenone C'
_chemical_name_systematic
;
6-(2-Chloro-1-hydroxy-2-phenylethyl)-2H-pyran-2-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.393(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.79348(19)
_cell_length_b                   27.8665(5)
_cell_length_c                   10.2288(3)
_cell_measurement_reflns_used    21920
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      30.3730
_cell_measurement_theta_min      2.2690
_cell_volume                     2317.49(11)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2018)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2018)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
ShelXL (Sheldrick, 2015a)
;
_computing_structure_solution
;
ShelXT (Sheldrick, 2015b)
;
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'HyPix Bantam HPC 3000'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            53946
_diffrn_reflns_theta_full        28.000
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         2.274
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.322
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2018)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.807
_refine_diff_density_min         -0.307
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         5716
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0395
_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)+(0.0419P)²+1.0958P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1025
_reflns_number_gt                4902
_reflns_number_total             5716
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vm2241sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        2317.49(10)
_cod_database_code               2243621
_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   0.871
_shelx_estimated_absorpt_t_max   0.956
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.32805(5) 0.27929(2) 0.32248(5) 0.03931(12) Uani d 1 . .
O O1 0.19539(12) 0.38851(4) 0.14334(12) 0.0280(2) Uani d 1 . .
C C2 0.06986(19) 0.41632(6) 0.15322(16) 0.0291(3) Uani d 1 . .
O O2 0.11024(14) 0.45514(4) 0.21042(13) 0.0358(3) Uani d 1 . .
C C3 -0.0917(2) 0.39555(6) 0.09867(19) 0.0371(4) Uani d 1 . .
H H3 -0.180630 0.412327 0.108707 0.045 Uiso calc 1 . .
C C4 -0.1185(2) 0.35297(7) 0.0340(2) 0.0410(4) Uani d 1 . .
H H4 -0.226415 0.339879 -0.002256 0.049 Uiso calc 1 . .
C C5 0.0135(2) 0.32706(6) 0.01912(19) 0.0375(4) Uani d 1 . .
H H5 -0.006149 0.297389 -0.030281 0.045 Uiso calc 1 . .
C C6 0.16559(19) 0.34516(5) 0.07573(16) 0.0286(3) Uani d 1 . .
C C7 0.32159(19) 0.32161(5) 0.08075(16) 0.0285(3) Uani d 1 . .
H H7 0.292338 0.289992 0.031228 0.034 Uiso calc 1 . .
O O7 0.40270(15) 0.34945(4) 0.01160(12) 0.0344(3) Uani d 1 . .
H H7A 0.450794 0.372588 0.063544 0.052 Uiso calc 1 . .
C C8 0.43932(19) 0.31233(5) 0.23401(17) 0.0284(3) Uani d 1 . .
H H8 0.469(2) 0.3433(7) 0.2880(19) 0.034 Uiso d 1 . .
C C9 0.5936(2) 0.28604(6) 0.24594(17) 0.0310(3) Uani d 1 . .
C C10 0.7444(2) 0.30839(7) 0.31029(19) 0.0377(4) Uani d 1 . .
H H10 0.749903 0.339773 0.348115 0.045 Uiso calc 1 . .
C C11 0.8882(2) 0.28497(8) 0.3197(2) 0.0489(5) Uani d 1 . .
H H11 0.991429 0.300479 0.363557 0.059 Uiso calc 1 . .
C C12 0.8810(3) 0.23955(8) 0.2659(2) 0.0541(5) Uani d 1 . .
H H12 0.979428 0.223647 0.273004 0.065 Uiso calc 1 . .
C C13 0.7311(3) 0.21688(8) 0.2013(2) 0.0538(5) Uani d 1 . .
H H13 0.726550 0.185437 0.164088 0.065 Uiso calc 1 . .
C C14 0.5870(2) 0.24015(6) 0.1907(2) 0.0423(4) Uani d 1 . .
H H14 0.483896 0.224657 0.145734 0.051 Uiso calc 1 . .
Cl Cl1A 0.93903(13) 0.57893(5) 0.49691(10) 0.0377(2) Uani d 0.846(4) A 1
O O1A 0.7230(4) 0.49234(15) 0.2049(4) 0.0260(6) Uani d 0.846(4) A 1
C C2A 0.5818(5) 0.46527(14) 0.1782(7) 0.0268(10) Uani d 0.846(4) A 1
O O2A 0.5979(6) 0.42183(13) 0.1788(7) 0.0329(8) Uani d 0.846(4) A 1
C C3A 0.4349(5) 0.49166(15) 0.1631(8) 0.0289(8) Uani d 0.846(4) A 1
H H3A 0.336315 0.474783 0.150149 0.035 Uiso calc 0.846(4) A 1
C C4A 0.4360(5) 0.53973(17) 0.1673(8) 0.0292(8) Uani d 0.846(4) A 1
H H4A 0.338434 0.556466 0.158285 0.035 Uiso calc 0.846(4) A 1
C C5A 0.5820(4) 0.56627(14) 0.1851(4) 0.0279(6) Uani d 0.846(4) A 1
H H5A 0.581503 0.600358 0.184988 0.033 Uiso calc 0.846(4) A 1
C C6A 0.7197(4) 0.54175(13) 0.2019(5) 0.0255(7) Uani d 0.846(4) A 1
C C7A 0.8852(2) 0.56233(7) 0.2189(2) 0.0252(4) Uani d 0.846(4) A 1
H H7AA 0.871051 0.597715 0.202525 0.030 Uiso calc 0.846(4) A 1
O O7A 0.9428(6) 0.5433(2) 0.1172(4) 0.0296(8) Uani d 0.846(4) A 1
H H7AB 0.980517 0.515579 0.141834 0.044 Uiso calc 0.846(4) A 1
C C8A 1.0153(2) 0.55472(7) 0.3678(2) 0.0260(5) Uani d 0.846(4) A 1
H H8A 1.031853 0.519406 0.384443 0.031 Uiso calc 0.846(4) A 1
C C9A 1.1797(3) 0.57712(10) 0.3931(2) 0.0263(4) Uani d 0.846(4) A 1
C C10A 1.1931(3) 0.62302(12) 0.3442(3) 0.0329(6) Uani d 0.846(4) A 1
H H10A 1.096421 0.640320 0.290083 0.040 Uiso calc 0.846(4) A 1
C C11A 1.3472(5) 0.64377(11) 0.3740(4) 0.0398(7) Uani d 0.846(4) A 1
H H11A 1.355195 0.675081 0.340479 0.048 Uiso calc 0.846(4) A 1
C C12A 1.4879(5) 0.61874(18) 0.4524(6) 0.0413(10) Uani d 0.846(4) A 1
H H12A 1.592855 0.632815 0.472912 0.050 Uiso calc 0.846(4) A 1
C C13A 1.4758(6) 0.57314(17) 0.5009(5) 0.0409(12) Uani d 0.846(4) A 1
H H13A 1.572739 0.556021 0.555407 0.049 Uiso calc 0.846(4) A 1
C C14A 1.3225(6) 0.55226(13) 0.4703(4) 0.0339(7) Uani d 0.846(4) A 1
H H14A 1.315444 0.520686 0.502562 0.041 Uiso calc 0.846(4) A 1
Cl Cl1B 0.9422(9) 0.5930(2) 0.4962(7) 0.0377(2) Uani d 0.154(4) A 2
O O1B 0.722(3) 0.4848(8) 0.206(4) 0.050(7) Uani d 0.154(4) A 2
C C2B 0.566(3) 0.4672(8) 0.186(4) 0.038(6) Uani d 0.154(4) A 2
O O2B 0.561(3) 0.4241(9) 0.156(4) 0.040(6) Uani d 0.154(4) A 2
C C3B 0.437(3) 0.5015(8) 0.151(5) 0.039(7) Uani d 0.154(4) A 2
H H3B 0.326106 0.491106 0.113594 0.047 Uiso calc 0.154(4) A 2
C C4B 0.471(3) 0.5473(9) 0.170(4) 0.026(4) Uani d 0.154(4) A 2
H H4B 0.387210 0.569887 0.162666 0.031 Uiso calc 0.154(4) A 2
C C5B 0.633(2) 0.5624(8) 0.202(3) 0.034(5) Uani d 0.154(4) A 2
H H5B 0.654777 0.595892 0.207136 0.041 Uiso calc 0.154(4) A 2
C C6B 0.7555(18) 0.5324(7) 0.226(3) 0.033(5) Uani d 0.154(4) A 2
C C7B 0.9378(11) 0.5427(4) 0.2782(11) 0.025(2) Uani d 0.154(4) A 2
H H7B 0.999780 0.516699 0.344603 0.030 Uiso calc 0.154(4) A 2
O O7B 0.975(3) 0.5408(11) 0.1509(18) 0.023(3) Uani d 0.154(4) A 2
H H7BA 1.035535 0.517152 0.155396 0.035 Uiso calc 0.154(4) A 2
C C8B 0.9942(12) 0.5899(4) 0.3448(11) 0.035(3) Uani d 0.154(4) A 2
H H8B 0.931756 0.615484 0.277003 0.042 Uiso calc 0.154(4) A 2
C C9B 1.1750(11) 0.5987(6) 0.3843(12) 0.0263(4) Uani d 0.154(4) A 2
C C10B 1.236(2) 0.6409(5) 0.3507(11) 0.034(3) Uani d 0.154(4) A 2
H H10B 1.162789 0.665177 0.297904 0.041 Uiso calc 0.154(4) A 2
C C11B 1.405(2) 0.6475(6) 0.394(2) 0.058(7) Uani d 0.154(4) A 2
H H11B 1.446986 0.676333 0.371466 0.069 Uiso calc 0.154(4) A 2
C C12B 1.5126(12) 0.6119(9) 0.472(3) 0.044(8) Uani d 0.154(4) A 2
H H12B 1.628029 0.616455 0.501574 0.052 Uiso calc 0.154(4) A 2
C C13B 1.4514(18) 0.5697(8) 0.505(3) 0.053(12) Uani d 0.154(4) A 2
H H13B 1.524873 0.545420 0.558122 0.064 Uiso calc 0.154(4) A 2
C C14B 1.283(2) 0.5631(5) 0.4616(19) 0.042(7) Uani d 0.154(4) A 2
H H14B 1.240675 0.534262 0.484561 0.050 Uiso calc 0.154(4) A 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'
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
C6 O1 C2 . . 121.84(12) ?
O1 C2 C3 . . 116.39(14) ?
O2 C2 O1 . . 116.01(14) ?
O2 C2 C3 . . 127.58(15) ?
C2 C3 H3 . . 119.6 ?
C4 C3 C2 . . 120.89(16) ?
C4 C3 H3 . . 119.6 ?
C3 C4 H4 . . 119.8 ?
C3 C4 C5 . . 120.40(16) ?
C5 C4 H4 . . 119.8 ?
C4 C5 H5 . . 120.5 ?
C6 C5 C4 . . 118.97(16) ?
C6 C5 H5 . . 120.5 ?
O1 C6 C7 . . 111.82(13) ?
C5 C6 O1 . . 121.31(15) ?
C5 C6 C7 . . 126.81(14) ?
C6 C7 H7 . . 108.2 ?
C6 C7 C8 . . 111.08(13) ?
O7 C7 C6 . . 111.80(12) ?
O7 C7 H7 . . 108.2 ?
O7 C7 C8 . . 109.33(12) ?
C8 C7 H7 . . 108.2 ?
C7 O7 H7A . . 109.5 ?
Cl1 C8 H8 . . 104.0(10) ?
C7 C8 Cl1 . . 108.20(10) ?
C7 C8 H8 . . 110.5(10) ?
C9 C8 Cl1 . . 110.65(10) ?
C9 C8 C7 . . 113.63(13) ?
C9 C8 H8 . . 109.4(10) ?
C10 C9 C8 . . 119.35(15) ?
C10 C9 C14 . . 119.42(16) ?
C14 C9 C8 . . 121.21(15) ?
C9 C10 H10 . . 119.9 ?
C9 C10 C11 . . 120.13(18) ?
C11 C10 H10 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C12 C11 C10 . . 120.19(19) ?
C12 C11 H11 . . 119.9 ?
C11 C12 H12 . . 119.9 ?
C11 C12 C13 . . 120.20(18) ?
C13 C12 H12 . . 119.9 ?
C12 C13 H13 . . 120.0 ?
C12 C13 C14 . . 119.93(19) ?
C14 C13 H13 . . 120.0 ?
C9 C14 C13 . . 120.12(19) ?
C9 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C6A O1A C2A . . 121.9(3) ?
O1A C2A C3A . . 116.2(3) ?
O2A C2A O1A . . 116.4(4) ?
O2A C2A C3A . . 127.2(4) ?
C2A C3A H3A . . 119.6 ?
C4A C3A C2A . . 120.7(4) ?
C4A C3A H3A . . 119.6 ?
C3A C4A H4A . . 119.5 ?
C3A C4A C5A . . 121.1(4) ?
C5A C4A H4A . . 119.5 ?
C4A C5A H5A . . 120.8 ?
C6A C5A C4A . . 118.3(3) ?
C6A C5A H5A . . 120.8 ?
O1A C6A C7A . . 111.4(3) ?
C5A C6A O1A . . 121.5(3) ?
C5A C6A C7A . . 127.1(3) ?
C6A C7A H7AA . . 107.6 ?
C6A C7A C8A . . 112.6(2) ?
O7A C7A C6A . . 111.7(3) ?
O7A C7A H7AA . . 107.6 ?
O7A C7A C8A . . 109.7(2) ?
C8A C7A H7AA . . 107.6 ?
C7A O7A H7AB . . 109.5 ?
Cl1A C8A H8A . . 108.1 ?
C7A C8A Cl1A . . 109.13(12) ?
C7A C8A H8A . . 108.1 ?
C9A C8A Cl1A . . 108.45(14) ?
C9A C8A C7A . . 114.75(15) ?
C9A C8A H8A . . 108.1 ?
C10A C9A C8A . . 121.7(2) ?
C14A C9A C8A . . 119.6(3) ?
C14A C9A C10A . . 118.7(2) ?
C9A C10A H10A . . 119.7 ?
C9A C10A C11A . . 120.6(2) ?
C11A C10A H10A . . 119.7 ?
C10A C11A H11A . . 120.0 ?
C12A C11A C10A . . 119.9(3) ?
C12A C11A H11A . . 120.0 ?
C11A C12A H12A . . 120.0 ?
C11A C12A C13A . . 119.9(3) ?
C13A C12A H12A . . 120.0 ?
C12A C13A H13A . . 119.9 ?
C12A C13A C14A . . 120.3(3) ?
C14A C13A H13A . . 119.9 ?
C9A C14A C13A . . 120.6(3) ?
C9A C14A H14A . . 119.7 ?
C13A C14A H14A . . 119.7 ?
C6B O1B C2B . . 120.5(18) ?
O1B C2B C3B . . 116.5(19) ?
O2B C2B O1B . . 108(2) ?
O2B C2B C3B . . 130(2) ?
C2B C3B H3B . . 119.8 ?
C4B C3B C2B . . 120(2) ?
C4B C3B H3B . . 119.8 ?
C3B C4B H4B . . 120.6 ?
C3B C4B C5B . . 119(2) ?
C5B C4B H4B . . 120.6 ?
C4B C5B H5B . . 118.6 ?
C6B C5B C4B . . 122.8(17) ?
C6B C5B H5B . . 118.6 ?
O1B C6B C7B . . 112.2(15) ?
C5B C6B O1B . . 118.7(16) ?
C5B C6B C7B . . 129.1(16) ?
C6B C7B H7B . . 109.4 ?
O7B C7B C6B . . 104.2(15) ?
O7B C7B H7B . . 109.4 ?
O7B C7B C8B . . 107.1(14) ?
C8B C7B C6B . . 117.1(12) ?
C8B C7B H7B . . 109.4 ?
C7B O7B H7BA . . 109.5 ?
Cl1B C8B H8B . . 108.4 ?
C7B C8B Cl1B . . 107.0(7) ?
C7B C8B H8B . . 108.4 ?
C7B C8B C9B . . 113.7(9) ?
C9B C8B Cl1B . . 110.8(8) ?
C9B C8B H8B . . 108.4 ?
C10B C9B C8B . . 122.7(13) ?
C10B C9B C14B . . 120.0 ?
C14B C9B C8B . . 117.2(13) ?
C9B C10B H10B . . 120.0 ?
C9B C10B C11B . . 120.0 ?
C11B C10B H10B . . 120.0 ?
C10B C11B H11B . . 120.0 ?
C10B C11B C12B . . 120.0 ?
C12B C11B H11B . . 120.0 ?
C11B C12B H12B . . 120.0 ?
C13B C12B C11B . . 120.0 ?
C13B C12B H12B . . 120.0 ?
C12B C13B H13B . . 120.0 ?
C14B C13B C12B . . 120.0 ?
C14B C13B H13B . . 120.0 ?
C9B C14B H14B . . 120.0 ?
C13B C14B C9B . . 120.0 ?
C13B 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
Cl1 C8 . 1.8162(15) ?
O1 C2 . 1.3837(18) ?
O1 C6 . 1.3668(18) ?
C2 O2 . 1.2166(19) ?
C2 C3 . 1.435(2) ?
C3 H3 . 0.9500 ?
C3 C4 . 1.335(3) ?
C4 H4 . 0.9500 ?
C4 C5 . 1.424(3) ?
C5 H5 . 0.9500 ?
C5 C6 . 1.337(2) ?
C6 C7 . 1.504(2) ?
C7 H7 . 1.0000 ?
C7 O7 . 1.4125(18) ?
C7 C8 . 1.536(2) ?
O7 H7A . 0.8400 ?
C8 H8 . 1.005(19) ?
C8 C9 . 1.505(2) ?
C9 C10 . 1.384(2) ?
C9 C14 . 1.390(2) ?
C10 H10 . 0.9500 ?
C10 C11 . 1.393(2) ?
C11 H11 . 0.9500 ?
C11 C12 . 1.372(3) ?
C12 H12 . 0.9500 ?
C12 C13 . 1.382(3) ?
C13 H13 . 0.9500 ?
C13 C14 . 1.391(3) ?
C14 H14 . 0.9500 ?
Cl1A C8A . 1.823(2) ?
O1A C2A . 1.388(4) ?
O1A C6A . 1.377(4) ?
C2A O2A . 1.218(4) ?
C2A C3A . 1.443(4) ?
C3A H3A . 0.9500 ?
C3A C4A . 1.340(4) ?
C4A H4A . 0.9500 ?
C4A C5A . 1.432(4) ?
C5A H5A . 0.9500 ?
C5A C6A . 1.342(4) ?
C6A C7A . 1.512(4) ?
C7A H7AA . 1.0000 ?
C7A O7A . 1.422(4) ?
C7A C8A . 1.531(3) ?
O7A H7AB . 0.8400 ?
C8A H8A . 1.0000 ?
C8A C9A . 1.504(3) ?
C9A C10A . 1.395(3) ?
C9A C14A . 1.387(4) ?
C10A H10A . 0.9500 ?
C10A C11A . 1.396(4) ?
C11A H11A . 0.9500 ?
C11A C12A . 1.380(6) ?
C12A H12A . 0.9500 ?
C12A C13A . 1.383(5) ?
C13A H13A . 0.9500 ?
C13A C14A . 1.390(5) ?
C14A H14A . 0.9500 ?
Cl1B C8B . 1.775(11) ?
O1B C2B . 1.399(18) ?
O1B C6B . 1.356(16) ?
C2B O2B . 1.235(18) ?
C2B C3B . 1.417(17) ?
C3B H3B . 0.9500 ?
C3B C4B . 1.310(17) ?
C4B H4B . 0.9500 ?
C4B C5B . 1.395(14) ?
C5B H5B . 0.9500 ?
C5B C6B . 1.314(14) ?
C6B C7B . 1.512(15) ?
C7B H7B . 1.0000 ?
C7B O7B . 1.458(17) ?
C7B C8B . 1.478(12) ?
O7B H7BA . 0.8400 ?
C8B H8B . 1.0000 ?
C8B C9B . 1.504(12) ?
C9B C10B . 1.3900 ?
C9B C14B . 1.3900 ?
C10B H10B . 0.9500 ?
C10B C11B . 1.3900 ?
C11B H11B . 0.9500 ?
C11B C12B . 1.3900 ?
C12B H12B . 0.9500 ?
C12B C13B . 1.3900 ?
C13B H13B . 0.9500 ?
C13B C14B . 1.3900 ?
C14B H14B . 0.9500 ?
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
O7 H7A O2A . 0.84 1.95 2.775(4) 169 yes
O7 H7A O2B . 0.84 1.79 2.63(3) 173 yes
O7A H7AB O2 1_655 0.84 2.01 2.835(6) 170 yes
O7B H7BA O2 1_655 0.84 1.86 2.63(3) 153 yes
C3 H3 O2A 1_455 0.95 2.33 3.220(6) 155 yes
C3 H3 O2B 1_455 0.95 2.52 3.42(4) 158 yes
C3A H3A O2 . 0.95 2.36 3.236(5) 153 yes
C5 H5 Cl1 4_565 0.95 2.70 3.6042(17) 159 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
Cl1 C8 C9 C10 . . . . -120.90(15) ?
Cl1 C8 C9 C14 . . . . 60.55(19) ?
O1 C2 C3 C4 . . . . -4.2(2) ?
O1 C6 C7 O7 . . . . -61.88(17) ?
O1 C6 C7 C8 . . . . 60.54(16) ?
C2 O1 C6 C5 . . . . -1.8(2) ?
C2 O1 C6 C7 . . . . -179.31(12) ?
C2 C3 C4 C5 . . . . 0.6(3) ?
O2 C2 C3 C4 . . . . 177.78(17) ?
C3 C4 C5 C6 . . . . 2.6(3) ?
C4 C5 C6 O1 . . . . -2.1(2) ?
C4 C5 C6 C7 . . . . 175.07(16) ?
C5 C6 C7 O7 . . . . 120.76(17) ?
C5 C6 C7 C8 . . . . -116.82(18) ?
C6 O1 C2 O2 . . . . -176.92(13) ?
C6 O1 C2 C3 . . . . 4.8(2) ?
C6 C7 C8 Cl1 . . . . 53.13(14) ?
C6 C7 C8 C9 . . . . 176.44(12) ?
C7 C8 C9 C10 . . . . 117.14(16) ?
C7 C8 C9 C14 . . . . -61.4(2) ?
O7 C7 C8 Cl1 . . . . 176.98(10) yes
O7 C7 C8 C9 . . . . -59.71(16) ?
C8 C9 C10 C11 . . . . -178.70(16) ?
C8 C9 C14 C13 . . . . 179.04(17) ?
C9 C10 C11 C12 . . . . -0.3(3) ?
C10 C9 C14 C13 . . . . 0.5(3) ?
C10 C11 C12 C13 . . . . 0.4(3) ?
C11 C12 C13 C14 . . . . 0.0(3) ?
C12 C13 C14 C9 . . . . -0.4(3) ?
C14 C9 C10 C11 . . . . -0.1(3) ?
Cl1A C8A C9A C10A . . . . -79.9(2) ?
Cl1A C8A C9A C14A . . . . 98.3(2) ?
O1A C2A C3A C4A . . . . 3.6(9) ?
O1A C6A C7A O7A . . . . 54.5(5) ?
O1A C6A C7A C8A . . . . -69.4(4) ?
C2A O1A C6A C5A . . . . 5.8(7) ?
C2A O1A C6A C7A . . . . -173.9(4) ?
C2A C3A C4A C5A . . . . 0.7(10) ?
O2A C2A C3A C4A . . . . 178.7(7) ?
C3A C4A C5A C6A . . . . -2.0(8) ?
C4A C5A C6A O1A . . . . -1.2(6) ?
C4A C5A C6A C7A . . . . 178.5(5) ?
C5A C6A C7A O7A . . . . -125.3(5) ?
C5A C6A C7A C8A . . . . 110.8(4) ?
C6A O1A C2A O2A . . . . 177.5(6) ?
C6A O1A C2A C3A . . . . -6.8(8) ?
C6A C7A C8A Cl1A . . . . -54.6(2) ?
C6A C7A C8A C9A . . . . -176.5(2) ?
C7A C8A C9A C10A . . . . 42.4(3) ?
C7A C8A C9A C14A . . . . -139.4(2) ?
O7A C7A C8A Cl1A . . . . -179.6(3) yes
O7A C7A C8A C9A . . . . 58.5(3) ?
C8A C9A C10A C11A . . . . 177.4(2) ?
C8A C9A C14A C13A . . . . -176.9(3) ?
C9A C10A C11A C12A . . . . 0.1(4) ?
C10A C9A C14A C13A . . . . 1.4(4) ?
C10A C11A C12A C13A . . . . 0.1(4) ?
C11A C12A C13A C14A . . . . 0.4(4) ?
C12A C13A C14A C9A . . . . -1.2(4) ?
C14A C9A C10A C11A . . . . -0.9(3) ?
Cl1B C8B C9B C10B . . . . -107.5(10) ?
Cl1B C8B C9B C14B . . . . 70.4(11) ?
O1B C2B C3B C4B . . . . -15(6) ?
O1B C6B C7B O7B . . . . 80(3) ?
O1B C6B C7B C8B . . . . -162(2) ?
C2B O1B C6B C5B . . . . -11(5) ?
C2B O1B C6B C7B . . . . 167(3) ?
C2B C3B C4B C5B . . . . 11(6) ?
O2B C2B C3B C4B . . . . -167(5) ?
C3B C4B C5B C6B . . . . -6(5) ?
C4B C5B C6B O1B . . . . 6(4) ?
C4B C5B C6B C7B . . . . -172(3) ?
C5B C6B C7B O7B . . . . -101(3) ?
C5B C6B C7B C8B . . . . 17(3) ?
C6B O1B C2B O2B . . . . 173(4) ?
C6B O1B C2B C3B . . . . 16(5) ?
C6B C7B C8B Cl1B . . . . 61.4(16) ?
C6B C7B C8B C9B . . . . -175.9(15) ?
C7B C8B C9B C10B . . . . 132.0(10) ?
C7B C8B C9B C14B . . . . -50.2(12) ?
O7B C7B C8B Cl1B . . . . 177.9(11) yes
O7B C7B C8B C9B . . . . -59.5(15) ?
C8B C9B C10B C11B . . . . 177.8(12) ?
C8B C9B C14B C13B . . . . -177.9(12) ?
C9B C10B C11B C12B . . . . 0.0 ?
C10B C9B C14B C13B . . . . 0.0 ?
C10B C11B C12B C13B . . . . 0.0 ?
C11B C12B C13B C14B . . . . 0.0 ?
C12B C13B C14B C9B . . . . 0.0 ?
C14B C9B C10B C11B . . . . 0.0 ?
