Cu(II)-Catalyzed Aerobic Hydroperoxidation of Meldrum's Acid Derivatives and Application in Intramolecular Oxidation: A Conceptual Blueprint for O(2)/H(2) Dihydroxylation.
Krabbe, Scott W.; Do, Dung T.; Johnson, Jeffrey S.; Organic letters 14 (2012) 5932–5935; doi:10.1021/ol302848m

data_1508768
_publ_section_title
;
 Cu(II)-Catalyzed Aerobic Hydroperoxidation of Meldrum's Acid Derivatives
 and Application in Intramolecular Oxidation: A Conceptual Blueprint for
 O(2)/H(2) Dihydroxylation.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5932
_journal_page_last               5935
_journal_paper_doi               10.1021/ol302848m
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C9 H12 I O5, C12 H24 N'
_chemical_formula_sum            'C21 H36 I N O5'
_chemical_formula_weight         509.41
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-03-27
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled Mar 20 2012 17:37:33, GUI svn.r4124)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.1800(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3142(2)
_cell_length_b                   16.8691(3)
_cell_length_c                   10.6959(2)
_cell_measurement_reflns_used    4405
_cell_measurement_temperature    100
_cell_measurement_theta_max      69.92
_cell_measurement_theta_min      4.31
_cell_volume                     2329.09(7)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54179
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11077
_diffrn_reflns_theta_full        70.07
_diffrn_reflns_theta_max         70.07
_diffrn_reflns_theta_min         4.31
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    11.044
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7955
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
R(int) was 0.0692 before and 0.0499 after correction.
The Ratio of minimum to maximum transmission is 0.7955.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.104
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.063
_refine_diff_density_max         1.007
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0592P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1110
_reflns_number_gt                3434
_reflns_number_total             4334
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302848m_si_002.cif
_cod_data_source_block           x1203011
_cod_database_code               1508768