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#$Date: 2019-11-04 08:50:26 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222273 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/36/4033699.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4033699
loop_
_publ_author_name
'Kaleta, Jiří'
'Rončević, Igor'
'Císařová, Ivana'
'Dračínský, Martin'
'Šolínová, Veronika'
'Kašička, Václav'
'Michl, Josef'
_publ_section_title
;
 Bridge-Chlorinated Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acids.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2448
_journal_page_last               2461
_journal_paper_doi               10.1021/acs.joc.8b02780
_journal_volume                  84
_journal_year                    2019
_chemical_compound_source        'Synthesized by Dr. Jiri Kaleta'
_chemical_formula_moiety         'C9 H10 Cl2 O4'
_chemical_formula_sum            'C9 H10 Cl2 O4'
_chemical_formula_weight         253.07
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 94.0800(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.6926(8)
_cell_length_b                   8.2181(4)
_cell_length_c                   17.5298(9)
_cell_measurement_reflns_used    9911
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.2137
_cell_measurement_theta_min      2.5270
_cell_volume                     2255.0(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12124
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.439
_diffrn_reflns_theta_min         5.059
_diffrn_source                   'I\mS  micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    5.148
_exptl_absorpt_correction_T_max  0.48
_exptl_absorpt_correction_T_min  0.37
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_description       prism
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.286
_exptl_crystal_size_mid          0.243
_exptl_crystal_size_min          0.168
_refine_diff_density_max         1.059
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2200
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0394
_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)+(0.0512P)²+6.1074P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1069
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2140
_reflns_number_total             2200
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b02780_si_006.cif
_cod_data_source_block           JK829
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4033699
_shelx_shelxl_version_number     2018/1
_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   0.321
_shelx_estimated_absorpt_t_max   0.478
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cl1 Cl 0.18826(3) 0.42465(7) 0.40195(3) 0.02834(18) Uani 1 1 d . .
Cl2 Cl 0.44793(3) 0.13464(7) 0.43741(3) 0.02924(18) Uani 1 1 d . .
O1 O 0.26719(10) -0.14412(19) 0.36271(10) 0.0292(4) Uani 1 1 d . .
O2 O 0.17677(10) 0.01680(18) 0.42269(8) 0.0225(3) Uani 1 1 d . .
O3 O 0.37813(11) 0.5515(2) 0.25297(9) 0.0335(4) Uani 1 1 d . .
O4 O 0.43281(10) 0.54941(19) 0.37465(8) 0.0235(3) Uani 1 1 d . .
C1 C 0.28385(13) 0.1431(2) 0.35877(11) 0.0184(4) Uani 1 1 d . .
C2 C 0.35053(13) 0.2381(3) 0.41092(12) 0.0209(4) Uani 1 1 d . .
H2 H 0.325541 0.295554 0.454397 0.025 Uiso 1 1 calc R U
C3 C 0.34322(13) 0.3349(3) 0.33521(11) 0.0189(4) Uani 1 1 d . .
C4 C 0.24501(13) 0.3111(3) 0.33524(12) 0.0220(4) Uani 1 1 d . .
H4 H 0.215858 0.310882 0.282626 0.026 Uiso 1 1 calc R U
C6 C 0.24198(13) -0.0117(3) 0.38015(11) 0.0191(4) Uani 1 1 d . .
C5 C 0.34175(15) 0.1692(3) 0.29098(12) 0.0249(5) Uani 1 1 d . .
H5A H 0.312219 0.169863 0.239162 0.030 Uiso 1 1 calc R U
H5B H 0.396079 0.107580 0.293662 0.030 Uiso 1 1 calc R U
C7 C 0.38641(13) 0.4893(3) 0.31516(11) 0.0195(4) Uani 1 1 d . .
C8 C 0.13163(17) -0.1261(3) 0.44614(15) 0.0344(6) Uani 1 1 d . .
H8A H 0.111683 -0.189089 0.400857 0.052 Uiso 1 1 calc R U
H8B H 0.082510 -0.092854 0.473967 0.052 Uiso 1 1 calc R U
H8C H 0.170105 -0.193279 0.479472 0.052 Uiso 1 1 calc R U
C9 C 0.47491(15) 0.7033(3) 0.36232(13) 0.0269(5) Uani 1 1 d . .
H9A H 0.517590 0.688682 0.324721 0.040 Uiso 1 1 calc R U
H9B H 0.503104 0.741602 0.410697 0.040 Uiso 1 1 calc R U
H9C H 0.432474 0.783736 0.343218 0.040 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C6 O2 C8 115.39(17)
C7 O4 C9 116.02(16)
C6 C1 C2 124.89(17)
C6 C1 C4 130.78(18)
C2 C1 C4 86.83(15)
C6 C1 C5 126.82(18)
C2 C1 C5 88.54(15)
C4 C1 C5 85.07(16)
C6 C1 C3 176.41(17)
C2 C1 C3 52.19(11)
C4 C1 C3 52.50(11)
C5 C1 C3 52.90(12)
C3 C2 C1 75.35(14)
C3 C2 Cl2 118.66(15)
C1 C2 Cl2 116.35(15)
C3 C2 H2 113.7
C1 C2 H2 113.7
Cl2 C2 H2 113.7
C7 C3 C2 129.29(18)
C7 C3 C4 125.06(18)
C2 C3 C4 87.00(15)
C7 C3 C5 127.85(17)
C2 C3 C5 88.57(16)
C4 C3 C5 84.89(16)
C7 C3 C1 177.46(17)
C2 C3 C1 52.46(11)
C4 C3 C1 52.47(12)
C5 C3 C1 52.66(11)
C1 C4 C3 75.02(14)
C1 C4 Cl1 119.73(15)
C3 C4 Cl1 118.42(15)
C1 C4 H4 112.9
C3 C4 H4 112.9
Cl1 C4 H4 112.9
O1 C6 O2 125.52(19)
O1 C6 C1 123.24(19)
O2 C6 C1 111.19(17)
C1 C5 C3 74.44(14)
C1 C5 H5A 116.1
C3 C5 H5A 116.1
C1 C5 H5B 116.1
C3 C5 H5B 116.1
H5A C5 H5B 113.0
O3 C7 O4 125.0(2)
O3 C7 C3 123.60(19)
O4 C7 C3 111.42(17)
O2 C8 H8A 109.5
O2 C8 H8B 109.5
H8A C8 H8B 109.5
O2 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O4 C9 H9A 109.5
O4 C9 H9B 109.5
H9A C9 H9B 109.5
O4 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C4 1.783(2)
Cl2 C2 1.782(2)
O1 C6 1.205(3)
O2 C6 1.329(3)
O2 C8 1.446(3)
O3 C7 1.203(3)
O4 C7 1.324(2)
O4 C9 1.450(3)
C1 C6 1.491(3)
C1 C2 1.550(3)
C1 C4 1.553(3)
C1 C5 1.561(3)
C1 C3 1.892(3)
C2 C3 1.545(3)
C2 H2 1.0000
C3 C7 1.492(3)
C3 C4 1.554(3)
C3 C5 1.566(3)
C4 H4 1.0000
C5 H5A 0.9900
C5 H5B 0.9900
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
