#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:38:54 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178400 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/22/4022260.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_4022260
loop_
_publ_author_name
'Timothy J. Donohoe'
'Kevin Blades'
'Peter R. Moore'
'Michael J. Waring'
'Jon J. G. Winter'
'Madeleine Helliwell'
'Nicholas J. Newcombe'
'Geoffrey Stemp'
_publ_section_title
;
 Directed Dihydroxylation of Cyclic Allylic Alcohols and
 Trichloroacetamides Using OsO₄/TMEDA
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7946
_journal_page_last               7956
_journal_paper_doi               10.1021/jo026161y
_journal_volume                  67
_journal_year                    2002
_chemical_formula_sum            'C13 H18 Cl3 N O5'
_chemical_formula_weight         374.63
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             1999-10-18
_audit_creation_method           'by teXsan v1.7'
_cell_angle_alpha                90.00
_cell_angle_beta                 93.721(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9186(15)
_cell_length_b                   12.083(2)
_cell_length_c                   13.501(3)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      39.6
_cell_measurement_theta_min      35.7
_cell_volume                     1777.4(6)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan (MSC, 1995)'
_computing_publication_material  'teXsan (MSC, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
SHELXS86 (Sheldrick, 1985)
;
_diffrn_ambient_temperature      296.2
_diffrn_measured_fraction_theta_full 0.898
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_device       'Rigaku AFC5R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3771
_diffrn_reflns_theta_full        77.77
_diffrn_reflns_theta_max         77.77
_diffrn_reflns_theta_min         4.92
_diffrn_standards_decay_%        -3.30
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.860
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.778
_exptl_absorpt_correction_type
;
\y scans (North,Phillips & Matthews, 1968)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.0024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0641
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0830P)²+1.3601P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1680
_refine_ls_wR_factor_ref         0.1905
_reflns_number_gt                2449
_reflns_number_total             3575
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo026161y_s7.cif
_cod_data_source_block           s769_SYN-46
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0830P)^2^+1.3601P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0830P)^2^+1.3601P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n     '
_cod_database_code               4022260
loop_
_symmetry_equiv_pos_as_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_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_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.15799(11) 0.05982(12) 0.59520(11) 0.1085(5) Uani 1 d .
Cl2 Cl 0.13593(11) 0.05330(14) 0.80648(11) 0.1100(5) Uani 1 d .
Cl3 Cl 0.19802(12) -0.14324(12) 0.70184(13) 0.1136(5) Uani 1 d .
O1 O -0.0622(3) -0.1427(2) 0.6560(2) 0.0812(8) Uani 1 d .
O2 O -0.2508(2) 0.08147(18) 0.82546(17) 0.0566(6) Uani 1 d .
O3 O -0.1705(4) -0.0491(3) 0.9297(3) 0.1181(14) Uani 1 d .
O4 O -0.4643(2) -0.04378(17) 0.84673(18) 0.0602(6) Uani 1 d .
O5 O -0.4575(3) -0.2203(2) 0.7987(2) 0.0782(8) Uani 1 d .
N1 N -0.1023(2) 0.0382(2) 0.6748(2) 0.0538(7) Uani 1 d .
H1 H -0.076(4) 0.100(4) 0.688(3) 0.076(13) Uiso 1 d .
C1 C 0.1103(3) -0.0219(3) 0.6947(3) 0.0693(10) Uani 1 d .
C2 C -0.0291(3) -0.0486(3) 0.6737(3) 0.0551(8) Uani 1 d .
C3 C -0.2349(3) 0.0296(3) 0.6558(2) 0.0525(7) Uani 1 d .
H3 H -0.2516 -0.0311 0.6087 0.063 Uiso 1 calc R
C4 C -0.2920(3) -0.0008(2) 0.7534(2) 0.0436(6) Uani 1 d .
H4 H -0.2602 -0.0731 0.7756 0.052 Uiso 1 calc R
C5 C -0.4321(3) -0.0044(2) 0.7494(3) 0.0496(7) Uani 1 d .
H5 H -0.4629 -0.0561 0.6977 0.059 Uiso 1 calc R
C6 C -0.4966(3) 0.1062(3) 0.7359(3) 0.0671(10) Uani 1 d .
H6A H -0.4527 0.1600 0.7780 0.081 Uiso 1 calc R
H6B H -0.5783 0.0990 0.7595 0.081 Uiso 1 calc R
C7 C -0.5089(4) 0.1522(4) 0.6307(4) 0.0951(15) Uani 1 d .
H7A H -0.5843 0.1228 0.5988 0.114 Uiso 1 calc R
H7B H -0.5196 0.2317 0.6357 0.114 Uiso 1 calc R
C8 C -0.4076(4) 0.1318(5) 0.5615(4) 0.0995(16) Uani 1 d .
H8A H -0.4201 0.0591 0.5321 0.119 Uiso 1 calc R
H8B H -0.4161 0.1855 0.5081 0.119 Uiso 1 calc R
C9 C -0.2811(4) 0.1375(4) 0.6057(4) 0.0819(13) Uani 1 d .
H9A H -0.2762 0.1964 0.6547 0.098 Uiso 1 calc R
H9B H -0.2270 0.1568 0.5542 0.098 Uiso 1 calc R
C10 C -0.1872(4) 0.0453(4) 0.9091(3) 0.0796(12) Uani 1 d .
C11 C -0.1414(6) 0.1439(5) 0.9690(4) 0.130(2) Uani 1 d .
H11A H -0.1778 0.1441 1.0318 0.195 Uiso 1 calc R
H11B H -0.1635 0.2106 0.9336 0.195 Uiso 1 calc R
H11C H -0.0537 0.1399 0.9797 0.195 Uiso 1 calc R
C12 C -0.4707(4) -0.1527(3) 0.8629(3) 0.0664(10) Uani 1 d .
C13 C -0.4924(6) -0.1748(4) 0.9689(4) 0.116(2) Uani 1 d .
H13A H -0.5192 -0.2499 0.9759 0.175 Uiso 1 calc R
H13B H -0.5544 -0.1254 0.9900 0.175 Uiso 1 calc R
H13C H -0.4176 -0.1634 1.0090 0.175 Uiso 1 calc R
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'
N N 0.0311 0.0180 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
3 1 -4
0 2 -4
0 3 -3
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C10 O2 C4 117.3(3)
C12 O4 C5 119.0(3)
C2 N1 C3 122.4(3)
C2 N1 H1 122(3)
C3 N1 H1 116(3)
C2 C1 Cl3 111.1(3)
C2 C1 Cl2 111.0(2)
Cl3 C1 Cl2 109.1(2)
C2 C1 Cl1 107.9(3)
Cl3 C1 Cl1 108.8(2)
Cl2 C1 Cl1 108.8(2)
O1 C2 N1 125.1(3)
O1 C2 C1 120.2(3)
N1 C2 C1 114.6(3)
N1 C3 C9 108.1(3)
N1 C3 C4 108.6(3)
C9 C3 C4 116.0(3)
N1 C3 H3 108.0
C9 C3 H3 108.0
C4 C3 H3 108.0
O2 C4 C5 108.1(2)
O2 C4 C3 106.7(2)
C5 C4 C3 115.9(3)
O2 C4 H4 108.6
C5 C4 H4 108.6
C3 C4 H4 108.6
O4 C5 C6 104.9(3)
O4 C5 C4 106.1(3)
C6 C5 C4 115.9(3)
O4 C5 H5 109.9
C6 C5 H5 109.9
C4 C5 H5 109.9
C5 C6 C7 116.5(4)
C5 C6 H6A 108.2
C7 C6 H6A 108.2
C5 C6 H6B 108.2
C7 C6 H6B 108.2
H6A C6 H6B 107.3
C8 C7 C6 119.5(3)
C8 C7 H7A 107.5
C6 C7 H7A 107.5
C8 C7 H7B 107.5
C6 C7 H7B 107.5
H7A C7 H7B 107.0
C9 C8 C7 116.6(5)
C9 C8 H8A 108.2
C7 C8 H8A 108.2
C9 C8 H8B 108.2
C7 C8 H8B 108.2
H8A C8 H8B 107.3
C8 C9 C3 114.3(4)
C8 C9 H9A 108.7
C3 C9 H9A 108.7
C8 C9 H9B 108.7
C3 C9 H9B 108.7
H9A C9 H9B 107.6
O3 C10 O2 124.6(4)
O3 C10 C11 126.5(5)
O2 C10 C11 108.9(5)
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O5 C12 O4 122.6(3)
O5 C12 C13 127.0(3)
O4 C12 C13 110.3(3)
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.773(4)
Cl2 C1 1.768(4)
Cl3 C1 1.751(4)
O1 C2 1.212(4)
O2 C10 1.360(5)
O2 C4 1.442(3)
O3 C10 1.184(5)
O4 C12 1.336(4)
O4 C5 1.462(4)
O5 C12 1.206(4)
N1 C2 1.320(4)
N1 C3 1.458(4)
N1 H1 0.82(4)
C1 C2 1.564(5)
C3 C9 1.539(5)
C3 C4 1.539(4)
C3 H3 0.9800
C4 C5 1.527(4)
C4 H4 0.9800
C5 C6 1.516(5)
C5 H5 0.9800
C6 C7 1.524(6)
C6 H6A 0.9700
C6 H6B 0.9700
C7 C8 1.513(7)
C7 H7A 0.9700
C7 H7B 0.9700
C8 C9 1.470(6)
C8 H8A 0.9700
C8 H8B 0.9700
C9 H9A 0.9700
C9 H9B 0.9700
C10 C11 1.507(6)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 C13 1.490(6)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
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
C3 N1 C2 O1 1.1(6)
C3 N1 C2 C1 179.4(3)
Cl3 C1 C2 O1 -6.5(5)
Cl2 C1 C2 O1 -128.1(3)
Cl1 C1 C2 O1 112.6(4)
Cl3 C1 C2 N1 175.1(3)
Cl2 C1 C2 N1 53.5(4)
Cl1 C1 C2 N1 -65.7(4)
C2 N1 C3 C9 -148.5(4)
C2 N1 C3 C4 84.8(4)
C10 O2 C4 C5 113.3(3)
C10 O2 C4 C3 -121.4(3)
N1 C3 C4 O2 54.8(3)
C9 C3 C4 O2 -67.1(4)
N1 C3 C4 C5 175.3(3)
C9 C3 C4 C5 53.4(4)
C12 O4 C5 C6 150.3(3)
C12 O4 C5 C4 -86.6(4)
O2 C4 C5 O4 -65.1(3)
C3 C4 C5 O4 175.2(2)
O2 C4 C5 C6 50.9(4)
C3 C4 C5 C6 -68.8(4)
O4 C5 C6 C7 -163.8(3)
C4 C5 C6 C7 79.7(4)
C5 C6 C7 C8 -34.5(6)
C6 C7 C8 C9 -39.0(7)
C7 C8 C9 C3 84.1(6)
N1 C3 C9 C8 166.7(4)
C4 C3 C9 C8 -71.0(5)
C4 O2 C10 O3 -5.3(7)
C4 O2 C10 C11 174.1(4)
C5 O4 C12 O5 -4.2(6)
C5 O4 C12 C13 174.4(4)
