#------------------------------------------------------------------------------
#$Date: 2018-06-07 07:24:32 +0300 (Thu, 07 Jun 2018) $
#$Revision: 208159 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/54/2015444.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_2015444
loop_
_publ_author_name
'Şahin, Ertan'
'Kelebekli, Latif'
'Kara, Yunus'
'Balci, Metin'
_publ_section_title
;(1SR,2SR,3SR,4RS,5RS,6RS,7SR,8RS)-7,8-Dichlorobicyclo[4.2.0]octa-2,3,4,5-tetrayl
 tetraacetate
;
_journal_coeditor_code           HJ3010
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o432
_journal_page_last               o434
_journal_paper_doi               10.1107/S0108270106018336
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C16 H20 Cl2 O8'
_chemical_formula_moiety         'C16 H20 Cl2 O8'
_chemical_formula_sum            'C16 H20 Cl2 O8'
_chemical_formula_weight         411.22
_chemical_name_systematic
;(1SR,2SR,3SR,4RS,5RS,6RS,7SR,8RS)-7,8-Dichlorobicyclo[4.2.0]octa-2,3,4,5-tetrayl
tetraacetate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                111.427(2)
_cell_angle_beta                 98.2810(10)
_cell_angle_gamma                108.8340(10)
_cell_formula_units_Z            2
_cell_length_a                   8.9489(5)
_cell_length_b                   11.0230(8)
_cell_length_c                   11.2885(7)
_cell_measurement_reflns_used    7762
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      33.1519
_cell_measurement_theta_min      2.5185
_cell_volume                     936.71(11)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Rigaku R-AXIS RAPID S'
_diffrn_measurement_method       oscillation
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            64683
_diffrn_reflns_theta_full        33.21
_diffrn_reflns_theta_max         33.21
_diffrn_reflns_theta_min         2.17
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 50
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.387
_exptl_absorpt_correction_T_max  0.926
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.263
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.321
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         7145
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.321
_refine_ls_R_factor_gt           0.076
_refine_ls_shift/su_max          0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0595P)²+0.3756P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1896
_reflns_number_gt                6532
_reflns_number_total             7145
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hj3010.cif
_cod_data_source_block           4b
_cod_original_cell_volume        936.70(10)
_cod_database_code               2015444
_cod_database_fobs_code          2015444
_cod_depositor_comments
;
 Updating space group information.

 Antanas Vaitkus,
 2018-05-07
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -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_refinement_flags
_atom_site_occupancy
C C1 0.4965(2) 0.61022(19) 0.77019(17) 0.0309(3) Uani d . 1
C C2 0.4544(2) 0.4592(2) 0.75323(18) 0.0330(3) Uani d . 1
C C3 0.2891(2) 0.3968(2) 0.7761(2) 0.0360(4) Uani d . 1
C C4 0.1506(2) 0.4225(2) 0.69984(19) 0.0356(4) Uani d . 1
C C5 0.1919(2) 0.5522(2) 0.67124(18) 0.0334(3) Uani d . 1
C C6 0.3678(2) 0.60502(19) 0.66193(17) 0.0314(3) Uani d . 1
C C7 0.1893(3) 0.2346(2) 0.6858(2) 0.0447(4) Uani d . 1
C C8 0.1028(2) 0.2742(2) 0.5867(2) 0.0430(4) Uani d . 1
C C9 0.6381(3) 0.3577(2) 0.8030(2) 0.0423(4) Uani d . 1
C C10 0.7875(3) 0.3840(3) 0.9028(3) 0.0567(6) Uani d . 1
C C11 0.5991(2) 0.8355(2) 0.96058(19) 0.0388(4) Uani d . 1
C C12 0.5772(4) 0.9116(3) 1.0926(2) 0.0553(6) Uani d . 1
C C13 0.0206(3) 0.6635(2) 0.7595(2) 0.0463(5) Uani d . 1
C C14 0.0142(3) 0.7843(3) 0.8721(3) 0.0739(9) Uani d . 1
C C15 0.5351(3) 0.7849(2) 0.61363(18) 0.0380(4) Uani d . 1
C C16 0.5744(3) 0.9313(3) 0.6258(3) 0.0543(6) Uani d . 1
Cl Cl1 0.05627(9) 0.15421(8) 0.76460(9) 0.0702(2) Uani d . 1
Cl Cl2 -0.10859(8) 0.17212(8) 0.49481(9) 0.0731(2) Uani d . 1
O O1 0.58777(17) 0.46418(16) 0.84715(14) 0.0399(3) Uani d . 1
O O2 0.5674(3) 0.2543(2) 0.6982(2) 0.0718(6) Uani d . 1
O O3 0.49473(16) 0.69586(14) 0.90194(12) 0.0343(3) Uani d . 1
O O4 0.6945(2) 0.88949(18) 0.91157(17) 0.0556(4) Uani d . 1
O O5 0.17410(16) 0.66642(15) 0.77633(14) 0.0384(3) Uani d . 1
O O6 -0.0960(2) 0.5712(2) 0.6667(2) 0.0735(6) Uani d . 1
O O7 0.40837(17) 0.74260(14) 0.66243(14) 0.0364(3) Uani d . 1
O O8 0.6049(2) 0.71054(18) 0.56760(16) 0.0477(4) Uani d . 1
H H1 0.603(3) 0.648(2) 0.761(2) 0.030(5) Uiso d . 1
H H10A 0.7554 0.3623 0.9728 0.085 Uiso calc R 1
H H10B 0.863 0.4824 0.9397 0.085 Uiso calc R 1
H H10C 0.8402 0.3243 0.8603 0.085 Uiso calc R 1
H H12A 0.6503 1.0109 1.1315 0.083 Uiso calc R 1
H H12B 0.6024 0.8708 1.1506 0.083 Uiso calc R 1
H H12C 0.4649 0.9021 1.0803 0.083 Uiso calc R 1
H H14A -0.0098 0.8477 0.8403 0.111 Uiso calc R 1
H H14B 0.119 0.8352 0.9401 0.111 Uiso calc R 1
H H14C -0.0708 0.7477 0.9085 0.111 Uiso calc R 1
H H16A 0.6382 0.947 0.5672 0.082 Uiso calc R 1
H H16B 0.6368 0.9997 0.716 0.082 Uiso calc R 1
H H16C 0.4735 0.9419 0.6019 0.082 Uiso calc R 1
H H2 0.460(3) 0.405(3) 0.662(2) 0.037(6) Uiso d . 1
H H3 0.306(3) 0.426(3) 0.872(3) 0.044(6) Uiso d . 1
H H4 0.066(3) 0.414(3) 0.743(2) 0.040(6) Uiso d . 1
H H5 0.111(3) 0.525(3) 0.586(3) 0.045(6) Uiso d . 1
H H6 0.368(3) 0.537(2) 0.575(2) 0.031(5) Uiso d . 1
H H7 0.246(3) 0.172(3) 0.654(2) 0.042(6) Uiso d . 1
H H8 0.157(3) 0.272(3) 0.526(2) 0.043(6) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 C2 C3 111.84(14) ?
C1 C2 H2 105.7(14) ?
C1 C6 C5 114.24(14) ?
C1 C6 H6 107.0(13) ?
C2 C1 C6 107.87(14) ?
C2 C1 H1 109.8(13) ?
C2 C3 C4 112.11(15) ?
C2 C3 C7 114.09(15) ?
C2 C3 H3 109.3(15) ?
C3 C2 H2 114.2(14) ?
C3 C4 H4 106.9(14) ?
C3 C7 Cl1 110.86(15) ?
C3 C7 H7 120.7(15) ?
C4 C3 H3 117.5(15) ?
C4 C5 C6 111.59(14) yes
C4 C5 H5 108.2(15) ?
C4 C8 C7 89.45(16) yes
C4 C8 Cl2 117.74(14) ?
C4 C8 H8 115.2(17) ?
C5 C4 C3 121.16(15) yes
C5 C4 C8 120.03(17) ?
C5 C4 H4 111.6(14) ?
C5 C6 H6 107.4(13) ?
C6 C1 H1 109.6(13) ?
C6 C5 H5 110.1(15) ?
C7 C3 C4 87.73(15) ?
C7 C3 H3 114.9(15) ?
C7 C8 Cl2 121.08(16) ?
C7 C8 H8 107.2(16) ?
C8 C4 C3 87.36(14) yes
C8 C4 H4 106.8(15) ?
C8 C7 C3 87.74(15) ?
C8 C7 Cl1 113.82(15) ?
C8 C7 H7 118.4(15) ?
C9 C10 H10A 109.5 ?
C9 C10 H10B 109.5 ?
C9 C10 H10C 109.5 ?
C9 O1 C2 116.51(15) ?
C11 C12 H12A 109.5 ?
C11 C12 H12B 109.5 ?
C11 C12 H12C 109.5 ?
C11 O3 C1 116.81(14) ?
C13 C14 H14A 109.5 ?
C13 C14 H14B 109.5 ?
C13 C14 H14C 109.5 ?
C13 O5 C5 115.46(15) ?
C15 C16 H16A 109.5 ?
C15 C16 H16B 109.5 ?
C15 C16 H16C 109.5 ?
C15 O7 C6 115.49(14) ?
Cl1 C7 H7 105.0(15) ?
Cl2 C8 H8 105.7(17) ?
O1 C2 C1 107.03(14) yes
O1 C2 C3 111.15(15) ?
O1 C2 H2 106.5(13) ?
O1 C9 C10 111.2(2) ?
O2 C9 C10 125.4(2) ?
O2 C9 O1 123.35(19) ?
O3 C1 C2 108.45(14) yes
O3 C1 C6 111.42(13) ?
O3 C1 H1 109.6(13) ?
O3 C11 C12 110.73(18) ?
O4 C11 C12 125.4(2) ?
O4 C11 O3 123.87(18) ?
O5 C13 C14 111.6(2) ?
O5 C5 C4 109.55(15) ?
O5 C5 C6 109.17(15) yes
O5 C5 H5 108.1(15) ?
O6 C13 C14 125.2(2) yes
O6 C13 O5 123.1(2) yes
O7 C15 C16 111.57(17) ?
O7 C6 C1 111.41(14) ?
O7 C6 C5 107.94(13) yes
O7 C6 H6 108.6(13) ?
O8 C15 C16 125.86(19) ?
O8 C15 O7 122.57(18) ?
H10A C10 H10B 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
H12A C12 H12B 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
H14A C14 H14B 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
H16A C16 H16B 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 H1 0.95(2) ?
C2 C1 1.514(3) yes
C2 C3 1.520(3) yes
C2 H2 1.00(2) ?
C3 C4 1.567(3) yes
C3 C7 1.552(3) yes
C3 H3 0.99(3) ?
C4 C8 1.534(3) yes
C4 H4 0.96(2) ?
C5 C4 1.522(3) yes
C5 C6 1.526(2) yes
C5 H5 1.00(3) ?
C6 C1 1.525(2) yes
C6 H6 0.99(2) ?
C7 C8 1.538(3) yes
C7 H7 0.98(3) ?
C8 H8 0.89(3) ?
C9 C10 1.489(3) ?
C10 H10A 0.96 ?
C10 H10B 0.96 ?
C10 H10C 0.96 ?
C11 C12 1.497(3) ?
C12 H12A 0.96 ?
C12 H12B 0.96 ?
C12 H12C 0.96 ?
C13 C14 1.492(3) ?
C14 H14A 0.96 ?
C14 H14B 0.96 ?
C14 H14C 0.96 ?
C15 C16 1.485(3) yes
C16 H16A 0.96 ?
C16 H16B 0.96 ?
C16 H16C 0.96 ?
Cl1 C7 1.788(2) yes
Cl2 C8 1.769(2) yes
O1 C2 1.450(2) ?
O1 C9 1.344(2) ?
O2 C9 1.197(3) ?
O3 C1 1.447(2) yes
O3 C11 1.353(2) ?
O4 C11 1.199(3) yes
O5 C13 1.348(2) yes
O5 C5 1.453(2) ?
O6 C13 1.201(3) ?
O7 C15 1.354(2) yes
O7 C6 1.439(2) ?
O8 C15 1.202(2) ?
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 O4 . 0.95(3) 2.35(2) 2.690(3) 100.5(17) ?
C1 H1 O8 . 0.95(3) 2.52(2) 3.031(3) 114.1(17) ?
C2 H2 O2 . 1.00(2) 2.29(3) 2.672(3) 100.9(18) ?
C2 H2 O8 2_666 1.00(2) 2.31(2) 3.279(2) 161(2) yes
C8 H8 O8 2_666 0.89(3) 2.50(3) 3.339(3) 158(2) 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
_geom_torsion_publ_flag
C1 C2 C3 C4 47.1(2) ?
C1 C2 C3 C7 144.89(17) yes
C1 O3 C11 C12 177.04(17) ?
C1 O3 C11 O4 -2.4(3) ?
C2 C3 C4 C5 -29.4(2) yes
C2 C3 C4 C8 94.47(17) yes
C2 C3 C7 C8 -92.65(17) ?
C2 C3 C7 Cl1 152.67(14) ?
C2 O1 C9 C10 173.39(18) ?
C2 O1 C9 O2 -8.5(3) ?
C3 C2 C1 C6 -64.25(18) ?
C3 C2 C1 O3 56.56(18) ?
C3 C4 C8 C7 20.85(14) yes
C3 C4 C8 Cl2 146.18(16) ?
C3 C7 C8 C4 -21.06(14) yes
C3 C7 C8 Cl2 -143.59(16) ?
C4 C3 C7 C8 20.60(14) ?
C4 C3 C7 Cl1 -94.08(15) ?
C4 C5 C6 C1 -43.8(2) ?
C4 C5 C6 O7 -168.35(14) yes
C5 C4 C8 C7 145.72(17) yes
C5 C4 C8 Cl2 -89.0(2) ?
C5 C6 C1 C2 63.27(18) ?
C5 C6 C1 O3 -55.66(19) ?
C5 O5 C13 C14 179.9(2) yes
C5 O5 C13 O6 2.2(3) ?
C6 C5 C4 C3 27.2(2) yes
C6 C5 C4 C8 -79.5(2) ?
C6 O7 C15 C16 -176.54(18) ?
C6 O7 C15 O8 3.1(3) ?
C7 C3 C4 C5 -144.56(17) yes
C7 C3 C4 C8 -20.67(15) ?
C9 O1 C2 C1 -138.95(17) ?
C9 O1 C2 C3 98.66(19) ?
C11 O3 C1 C2 149.13(15) ?
C11 O3 C1 C6 -92.29(18) ?
C13 O5 C5 C4 -86.5(2) ?
C13 O5 C5 C6 151.07(17) ?
C15 O7 C6 C1 73.77(18) ?
C15 O7 C6 C5 -160.03(15) ?
Cl1 C7 C8 C4 90.79(16) ?
Cl1 C7 C8 Cl2 -31.7(2) ?
O1 C2 C1 C6 173.79(13) ?
O1 C2 C1 O3 -65.40(16) ?
O1 C2 C3 C4 166.70(14) ?
O1 C2 C3 C7 -95.55(19) ?
O5 C5 C4 C3 -93.81(18) ?
O5 C5 C4 C8 159.49(15) ?
O5 C5 C6 C1 77.40(18) ?
O5 C5 C6 O7 -47.11(18) ?
O7 C6 C1 C2 -174.09(13) ?
O7 C6 C1 O3 66.98(17) ?
