#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/47/1504736.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_1504736
loop_
_publ_author_name
'Khan, Faiz Ahmed'
'Sudheer, Ch'
_publ_section_title
;
 A chiral pool approach to the synthesis of optically active tetrahalo
 norbornyl building blocks.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3029
_journal_page_last               3032
_journal_paper_doi               10.1021/ol800990m
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C12 H12 Cl4 O5'
_chemical_formula_sum            'C12 H12 Cl4 O5'
_chemical_formula_weight         378.02
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3550(7)
_cell_length_b                   13.6917(12)
_cell_length_c                   14.3079(13)
_cell_measurement_reflns_used    2667
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.85
_cell_volume                     1440.8(2)
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_molecular_graphics    'Diamond 2.1'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-92
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area Detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0526
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9426
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        0.5
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.838
_exptl_absorpt_correction_T_max  0.9444
_exptl_absorpt_correction_T_min  0.9299
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS 2.10 (Bruker 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3540
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0323P)²+2.8529P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.1145
_reflns_number_gt                3098
_reflns_number_total             3540
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol800990m-file003.cif
_cod_data_source_block           22
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               1504736
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.4237(5) 0.4660(3) 0.1158(3) 0.0190(8) Uani 1 1 d .
C2 C 0.3159(5) 0.3945(3) 0.0512(3) 0.0188(8) Uani 1 1 d .
H2 H 0.1875 0.3896 0.0689 0.023 Uiso 1 1 calc R
C3 C 0.3413(5) 0.4374(3) -0.0480(3) 0.0162(7) Uani 1 1 d .
H3 H 0.2251 0.4624 -0.0714 0.019 Uiso 1 1 calc R
C4 C 0.4733(5) 0.5238(3) -0.0276(3) 0.0162(7) Uani 1 1 d .
C5 C 0.6530(5) 0.4881(3) 0.0113(3) 0.0180(7) Uani 1 1 d .
C6 C 0.6242(5) 0.4539(3) 0.0977(3) 0.0209(8) Uani 1 1 d .
C7 C 0.3874(5) 0.5654(3) 0.0653(3) 0.0194(8) Uani 1 1 d .
C8 C 0.1393(6) 0.6703(3) 0.0220(3) 0.0293(10) Uani 1 1 d .
H8A H 0.0092 0.6739 0.0265 0.044 Uiso 1 1 calc R
H8B H 0.1744 0.6699 -0.0426 0.044 Uiso 1 1 calc R
H8C H 0.1923 0.7259 0.0525 0.044 Uiso 1 1 calc R
C9 C 0.4548(7) 0.6847(3) 0.1828(3) 0.0318(11) Uani 1 1 d .
H9A H 0.5332 0.7395 0.1942 0.048 Uiso 1 1 calc R
H9B H 0.4769 0.6352 0.2289 0.048 Uiso 1 1 calc R
H9C H 0.3303 0.7054 0.1863 0.048 Uiso 1 1 calc R
C10 C 0.4078(5) 0.2957(3) 0.0474(3) 0.0199(8) Uani 1 1 d .
C11 C 0.4005(5) 0.3488(3) -0.1058(3) 0.0195(8) Uani 1 1 d .
H11 H 0.2907 0.3198 -0.1329 0.023 Uiso 1 1 calc R
C12 C 0.5354(6) 0.3638(3) -0.1845(3) 0.0225(8) Uani 1 1 d .
H12A H 0.4861 0.4101 -0.2292 0.027 Uiso 1 1 calc R
H12B H 0.6472 0.3908 -0.1595 0.027 Uiso 1 1 calc R
O1 O 0.4906(4) 0.64605(19) 0.09191(18) 0.0196(6) Uani 1 1 d .
O2 O 0.2025(4) 0.58172(19) 0.0666(2) 0.0212(6) Uani 1 1 d .
O3 O 0.4298(4) 0.2401(2) 0.1109(2) 0.0259(6) Uani 1 1 d .
O4 O 0.4751(4) 0.27858(19) -0.03897(19) 0.0210(6) Uani 1 1 d .
O5 O 0.5730(4) 0.2737(2) -0.2303(2) 0.0295(7) Uani 1 1 d .
H5 H 0.6453 0.2830 -0.2730 0.044 Uiso 1 1 calc R
Cl1 Cl 0.49310(14) 0.60880(7) -0.11980(6) 0.0229(2) Uani 1 1 d .
Cl2 Cl 0.35469(16) 0.45478(7) 0.23355(7) 0.0283(2) Uani 1 1 d .
Cl3 Cl 0.77670(15) 0.40369(8) 0.17201(8) 0.0321(3) Uani 1 1 d .
Cl4 Cl 0.85475(14) 0.49306(8) -0.04654(8) 0.0306(3) Uani 1 1 d .
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'
O O 0.0106 0.0060 '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
C6 C1 C2 109.0(3)
C6 C1 C7 100.6(3)
C2 C1 C7 100.7(3)
C6 C1 Cl2 115.8(3)
C2 C1 Cl2 111.3(3)
C7 C1 Cl2 117.9(3)
C10 C2 C3 104.6(3)
C10 C2 C1 110.8(3)
C3 C2 C1 104.1(3)
C11 C3 C2 103.3(3)
C11 C3 C4 121.7(3)
C2 C3 C4 101.0(3)
C5 C4 C3 111.6(3)
C5 C4 C7 99.0(3)
C3 C4 C7 100.5(3)
C5 C4 Cl1 114.5(3)
C3 C4 Cl1 114.4(3)
C7 C4 Cl1 115.1(3)
C6 C5 C4 108.3(3)
C6 C5 Cl4 126.9(3)
C4 C5 Cl4 124.8(3)
C5 C6 C1 105.9(3)
C5 C6 Cl3 128.2(3)
C1 C6 Cl3 125.9(3)
O2 C7 O1 113.9(3)
O2 C7 C1 107.7(3)
O1 C7 C1 118.0(3)
O2 C7 C4 117.7(3)
O1 C7 C4 107.3(3)
C1 C7 C4 90.4(3)
O3 C10 O4 122.3(4)
O3 C10 C2 127.0(4)
O4 C10 C2 110.6(3)
O4 C11 C12 109.3(3)
O4 C11 C3 105.9(3)
C12 C11 C3 118.7(3)
O5 C12 C11 110.6(3)
C7 O1 C9 116.2(3)
C7 O2 C8 116.6(3)
C10 O4 C11 110.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.507(6)
C1 C2 1.563(5)
C1 C7 1.564(5)
C1 Cl2 1.766(4)
C2 C10 1.514(5)
C2 C3 1.547(5)
C3 C11 1.531(5)
C3 C4 1.558(5)
C4 C5 1.515(5)
C4 C7 1.578(5)
C4 Cl1 1.765(4)
C5 C6 1.340(5)
C5 Cl4 1.700(4)
C6 Cl3 1.691(4)
C7 O2 1.378(5)
C7 O1 1.393(5)
C8 O2 1.447(5)
C9 O1 1.429(5)
C10 O3 1.196(5)
C10 O4 1.351(5)
C11 O4 1.463(5)
C11 C12 1.514(5)
C12 O5 1.425(5)
