#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:21:06 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178779 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/33/4103315.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_4103315
loop_
_publ_author_name
'James C. Griffith'
'Kevin M. Jones'
'Sylvain Picon'
'Michael J. Rawling'
'Benson M. Kariuki'
'Matthew Campbell'
'Nicholas C. O. Tomkinson'
_publ_contact_author
;
B. Kariuki,
School of Chemistry,
Cardiff University,
Main Building
Park Place
Cardiff
CF10 3AT
;
_publ_contact_author_email       kariukib@cardiff.ac.uk
_publ_section_title
;
 Alkene Syn Dihydroxylation with Malonoyl Peroxides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14409
_journal_page_last               14411
_journal_paper_doi               10.1021/ja1066674
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C6 H6 O4'
_chemical_formula_sum            'C6 H6 O4'
_chemical_formula_weight         142.11
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_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                 91.908(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.4920(7)
_cell_length_b                   6.1380(6)
_cell_length_c                   7.6100(8)
_cell_measurement_reflns_used    640
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      4.06
_cell_volume                     303.07(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997'
_computing_molecular_graphics    'Ortep-99 for Windows (Farrugia, 1995)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Sir-92 (A. Altomare et al., 1992)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD 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  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            1237
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         4.06
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.9737
_exptl_absorpt_correction_T_min  0.9737
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   Denzo/Scalepack
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             148
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     58
_refine_ls_number_reflns         739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0465
_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)+(0.0389P)²+0.1440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1127
_reflns_number_gt                640
_reflns_number_total             739
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1066674_si_004.cif
_cod_data_source_block           nct0805
_cod_database_code               4103315
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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 0.7659(3) 0.2500 0.0087(3) 0.0231(5) Uani 1 2 d S
C2 C 0.8290(3) 0.2500 0.1985(2) 0.0208(5) Uani 1 2 d S
C3 C 1.0577(3) 0.2500 0.1984(3) 0.0252(5) Uani 1 2 d S
C4 C 0.7316(2) 0.0738(3) 0.31912(18) 0.0263(4) Uani 1 1 d .
H4A H 0.6074 0.0081 0.2685 0.032 Uiso 1 1 calc R
H4B H 0.8285 -0.0370 0.3598 0.032 Uiso 1 1 calc R
C5 C 0.6901(4) 0.2500 0.4572(3) 0.0295(5) Uani 1 2 d S
H5A H 0.5498 0.2500 0.4973 0.035 Uiso 1 2 calc SR
H5B H 0.7886 0.2500 0.5559 0.035 Uiso 1 2 calc SR
O1 O 0.9411(2) 0.2500 -0.09280(18) 0.0292(4) Uani 1 2 d S
O2 O 1.1248(2) 0.2500 0.0271(2) 0.0300(4) Uani 1 2 d S
O3 O 0.6024(3) 0.2500 -0.0650(2) 0.0347(4) Uani 1 2 d S
O4 O 1.1845(3) 0.2500 0.3152(2) 0.0397(5) Uani 1 2 d S
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0298(11) 0.0196(10) 0.0201(10) 0.000 0.0021(8) 0.000
C2 0.0249(10) 0.0199(10) 0.0176(9) 0.000 0.0019(7) 0.000
C3 0.0281(11) 0.0224(10) 0.0253(10) 0.000 0.0017(8) 0.000
C4 0.0329(8) 0.0240(8) 0.0224(7) 0.0032(6) 0.0048(6) -0.0032(6)
C5 0.0351(12) 0.0329(12) 0.0209(10) 0.000 0.0066(9) 0.000
O1 0.0353(9) 0.0336(9) 0.0188(7) 0.000 0.0042(6) 0.000
O2 0.0264(8) 0.0353(9) 0.0287(8) 0.000 0.0065(6) 0.000
O3 0.0354(9) 0.0404(10) 0.0277(8) 0.000 -0.0069(7) 0.000
O4 0.0312(9) 0.0513(11) 0.0360(9) 0.000 -0.0076(7) 0.000
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O3 C1 O1 118.17(18) . .
O3 C1 C2 132.31(19) . .
O1 C1 C2 109.52(17) . .
C3 C2 C1 104.01(16) . .
C3 C2 C4 115.08(12) . .
C1 C2 C4 117.75(12) . .
C3 C2 C4 115.08(12) . 4_565
C1 C2 C4 117.75(12) . 4_565
C4 C2 C4 87.42(14) . 4_565
O4 C3 O2 118.05(19) . .
O4 C3 C2 131.7(2) . .
O2 C3 C2 110.22(17) . .
C5 C4 C2 89.89(11) . .
C5 C4 H4A 113.7 . .
C2 C4 H4A 113.7 . .
C5 C4 H4B 113.7 . .
C2 C4 H4B 113.7 . .
H4A C4 H4B 110.9 . .
C4 C5 C4 89.37(15) 4_565 .
C4 C5 H5A 113.8 4_565 .
C4 C5 H5A 113.8 . .
C4 C5 H5B 113.8 4_565 .
C4 C5 H5B 113.8 . .
H5A C5 H5B 111.0 . .
C1 O1 O2 108.32(14) . .
C3 O2 O1 107.93(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O3 1.184(3) .
C1 O1 1.396(3) .
C1 C2 1.489(3) .
C2 C3 1.485(3) .
C2 C4 1.565(2) .
C2 C4 1.565(2) 4_565
C3 O4 1.191(3) .
C3 O2 1.388(3) .
C4 C5 1.538(2) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C4 1.538(2) 4_565
C5 H5A 0.9700 .
C5 H5B 0.9700 .
O1 O2 1.477(2) .
