#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/87/1508768.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_1508768
loop_
_publ_author_name
'Krabbe, Scott W.'
'Do, Dung T.'
'Johnson, Jeffrey S.'
_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       'ω and φ 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 λ/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/[σ²(Fo²)+(0.0592P)²+0.0000P] where P=(Fo²+2Fc²)/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
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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
I1 I 0.40253(2) 0.43013(2) 0.32891(3) 0.03811(13) Uani 1 1 d .
O1 O 0.2726(2) 0.6388(2) 0.4706(3) 0.0300(7) Uani 1 1 d .
O2 O 0.2036(2) 0.74440(18) 0.1874(3) 0.0247(6) Uani 1 1 d .
H2 H 0.1608 0.7413 0.1154 0.037 Uiso 1 1 calc R
O3 O 0.0813(2) 0.63195(19) 0.0654(3) 0.0272(7) Uani 1 1 d .
O4 O 0.1070(2) 0.55481(19) 0.2405(3) 0.0309(7) Uani 1 1 d .
O5 O 0.1432(3) 0.72591(19) 0.4208(3) 0.0308(7) Uani 1 1 d .
C1 C 0.3116(4) 0.5076(3) 0.4168(4) 0.0334(11) Uani 1 1 d .
H1C H 0.2373 0.4995 0.3754 0.040 Uiso 1 1 calc R
H1D H 0.3231 0.4939 0.5092 0.040 Uiso 1 1 calc R
C2 C 0.3390(3) 0.5939(3) 0.4045(4) 0.0274(10) Uani 1 1 d .
H2A H 0.4131 0.6024 0.4505 0.033 Uiso 1 1 calc R
C3 C 0.3193(3) 0.6301(3) 0.2679(4) 0.0263(9) Uani 1 1 d .
H3 H 0.3144 0.5865 0.2032 0.032 Uiso 1 1 calc R
C4 C 0.2118(3) 0.6704(3) 0.2493(4) 0.0215(9) Uani 1 1 d .
C5 C 0.2024(3) 0.6826(3) 0.3871(4) 0.0246(9) Uani 1 1 d .
C6 C 0.4056(4) 0.6885(3) 0.2546(5) 0.0377(12) Uani 1 1 d .
H6 H 0.3815 0.7156 0.1693 0.045 Uiso 1 1 calc R
C7 C 0.4275(4) 0.7536(3) 0.3588(6) 0.0425(12) Uani 1 1 d .
H7A H 0.3634 0.7826 0.3572 0.064 Uiso 1 1 calc R
H7B H 0.4795 0.7904 0.3416 0.064 Uiso 1 1 calc R
H7C H 0.4535 0.7293 0.4437 0.064 Uiso 1 1 calc R
C8 C 0.5048(5) 0.6449(4) 0.2529(7) 0.0605(18) Uani 1 1 d .
H8A H 0.5294 0.6160 0.3341 0.091 Uiso 1 1 calc R
H8B H 0.5577 0.6832 0.2427 0.091 Uiso 1 1 calc R
H8C H 0.4916 0.6074 0.1808 0.091 Uiso 1 1 calc R
C9 C 0.1236(3) 0.6137(3) 0.1785(4) 0.0218(9) Uani 1 1 d .
N1 N -0.0448(3) 0.4429(2) 0.1715(3) 0.0233(7) Uani 1 1 d .
H1A H 0.0066 0.4806 0.1831 0.028 Uiso 1 1 calc R
H1B H -0.0533 0.4231 0.0893 0.028 Uiso 1 1 calc R
C10 C 0.0146(4) 0.4054(3) 0.4043(4) 0.0288(10) Uani 1 1 d .
H10A H 0.0610 0.4522 0.4162 0.035 Uiso 1 1 calc R
H10B H -0.0515 0.4216 0.4234 0.035 Uiso 1 1 calc R
C11 C 0.0647(4) 0.3395(3) 0.4967(4) 0.0336(11) Uani 1 1 d .
H11A H 0.0821 0.3603 0.5860 0.040 Uiso 1 1 calc R
H11B H 0.0144 0.2957 0.4922 0.040 Uiso 1 1 calc R
C12 C 0.1627(4) 0.3073(3) 0.4653(4) 0.0347(11) Uani 1 1 d .
H12A H 0.1900 0.2626 0.5237 0.042 Uiso 1 1 calc R
H12B H 0.2162 0.3493 0.4791 0.042 Uiso 1 1 calc R
C13 C 0.1396(4) 0.2791(3) 0.3257(5) 0.0344(11) Uani 1 1 d .
H13A H 0.2047 0.2610 0.3057 0.041 Uiso 1 1 calc R
H13B H 0.0916 0.2333 0.3146 0.041 Uiso 1 1 calc R
C14 C 0.0914(3) 0.3443(3) 0.2316(4) 0.0265(9) Uani 1 1 d .
H14A H 0.1419 0.3878 0.2357 0.032 Uiso 1 1 calc R
H14B H 0.0737 0.3230 0.1427 0.032 Uiso 1 1 calc R
C15 C -0.0057(3) 0.3762(3) 0.2645(4) 0.0228(9) Uani 1 1 d .
H15 H -0.0591 0.3333 0.2508 0.027 Uiso 1 1 calc R
C16 C -0.1435(3) 0.4843(3) 0.1770(4) 0.0240(9) Uani 1 1 d .
H16 H -0.1320 0.5128 0.2613 0.029 Uiso 1 1 calc R
C17 C -0.1664(3) 0.5452(3) 0.0691(5) 0.0277(9) Uani 1 1 d .
H17A H -0.1701 0.5184 -0.0143 0.033 Uiso 1 1 calc R
H17B H -0.1093 0.5844 0.0832 0.033 Uiso 1 1 calc R
C18 C -0.2687(4) 0.5883(3) 0.0633(5) 0.0340(11) Uani 1 1 d .
H18A H -0.2625 0.6195 0.1432 0.041 Uiso 1 1 calc R
H18B H -0.2834 0.6254 -0.0106 0.041 Uiso 1 1 calc R
C19 C -0.3574(4) 0.5297(3) 0.0487(5) 0.0332(11) Uani 1 1 d .
H19A H -0.3669 0.5008 -0.0340 0.040 Uiso 1 1 calc R
H19B H -0.4224 0.5584 0.0479 0.040 Uiso 1 1 calc R
C20 C -0.3338(4) 0.4711(3) 0.1602(5) 0.0353(11) Uani 1 1 d .
H20A H -0.3917 0.4330 0.1499 0.042 Uiso 1 1 calc R
H20B H -0.3281 0.5001 0.2421 0.042 Uiso 1 1 calc R
C21 C -0.2328(4) 0.4255(3) 0.1672(5) 0.0299(10) Uani 1 1 d .
H21A H -0.2179 0.3901 0.2434 0.036 Uiso 1 1 calc R
H21B H -0.2401 0.3923 0.0891 0.036 Uiso 1 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'
I I -0.3257 6.8362 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 O1 C2 111.5(3)
C4 O2 H2 109.5
I1 C1 H1C 109.2
I1 C1 H1D 109.2
H1C C1 H1D 107.9
C2 C1 I1 111.9(3)
C2 C1 H1C 109.2
C2 C1 H1D 109.2
O1 C2 C1 105.6(4)
O1 C2 H2A 109.0
O1 C2 C3 105.6(3)
C1 C2 H2A 109.0
C1 C2 C3 118.3(4)
C3 C2 H2A 109.0
C2 C3 H3 109.3
C2 C3 C4 103.3(3)
C2 C3 C6 112.4(4)
C4 C3 H3 109.3
C6 C3 H3 109.3
C6 C3 C4 113.0(4)
O2 C4 C3 114.3(3)
O2 C4 C5 108.6(3)
O2 C4 C9 110.7(3)
C3 C4 C9 110.8(3)
C5 C4 C3 103.2(3)
C5 C4 C9 108.8(3)
O1 C5 C4 111.0(4)
O5 C5 O1 122.6(4)
O5 C5 C4 126.4(4)
C3 C6 H6 107.2
C7 C6 C3 113.7(4)
C7 C6 H6 107.2
C8 C6 C3 111.2(5)
C8 C6 H6 107.2
C8 C6 C7 110.1(5)
C6 C7 H7A 109.5
C6 C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7B 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C6 C8 H8A 109.5
C6 C8 H8B 109.5
C6 C8 H8C 109.5
H8A C8 H8B 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O3 C9 O4 128.3(4)
O3 C9 C4 115.4(4)
O4 C9 C4 116.2(3)
H1A N1 H1B 107.0
C15 N1 H1A 107.6
C15 N1 H1B 107.6
C16 N1 H1A 107.6
C16 N1 H1B 107.6
C16 N1 C15 119.0(3)
H10A C10 H10B 108.2
C11 C10 H10A 109.7
C11 C10 H10B 109.7
C11 C10 C15 109.9(4)
C15 C10 H10A 109.7
C15 C10 H10B 109.7
C10 C11 H11A 109.2
C10 C11 H11B 109.2
H11A C11 H11B 107.9
C12 C11 C10 112.2(4)
C12 C11 H11A 109.2
C12 C11 H11B 109.2
C11 C12 H12A 109.6
C11 C12 H12B 109.6
C11 C12 C13 110.4(4)
H12A C12 H12B 108.1
C13 C12 H12A 109.6
C13 C12 H12B 109.6
C12 C13 H13A 109.2
C12 C13 H13B 109.2
H13A C13 H13B 107.9
C14 C13 C12 111.9(4)
C14 C13 H13A 109.2
C14 C13 H13B 109.2
C13 C14 H14A 109.6
C13 C14 H14B 109.6
H14A C14 H14B 108.1
C15 C14 C13 110.3(4)
C15 C14 H14A 109.6
C15 C14 H14B 109.6
N1 C15 C10 110.7(3)
N1 C15 C14 106.7(3)
N1 C15 H15 109.0
C10 C15 H15 109.0
C14 C15 C10 112.5(4)
C14 C15 H15 109.0
N1 C16 H16 108.5
N1 C16 C17 107.4(3)
N1 C16 C21 111.6(4)
C17 C16 H16 108.5
C17 C16 C21 112.2(4)
C21 C16 H16 108.5
C16 C17 H17A 109.4
C16 C17 H17B 109.4
C16 C17 C18 111.2(4)
H17A C17 H17B 108.0
C18 C17 H17A 109.4
C18 C17 H17B 109.4
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 108.0
C19 C18 C17 110.9(4)
C19 C18 H18A 109.5
C19 C18 H18B 109.5
C18 C19 H19A 109.7
C18 C19 H19B 109.7
C18 C19 C20 109.6(4)
H19A C19 H19B 108.2
C20 C19 H19A 109.7
C20 C19 H19B 109.7
C19 C20 H20A 109.2
C19 C20 H20B 109.2
C19 C20 C21 112.0(4)
H20A C20 H20B 107.9
C21 C20 H20A 109.2
C21 C20 H20B 109.2
C16 C21 C20 109.5(4)
C16 C21 H21A 109.8
C16 C21 H21B 109.8
C20 C21 H21A 109.8
C20 C21 H21B 109.8
H21A C21 H21B 108.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C1 2.148(5)
O1 C2 1.470(5)
O1 C5 1.346(5)
O2 H2 0.8400
O2 C4 1.405(5)
O3 C9 1.241(5)
O4 C9 1.244(5)
O5 C5 1.193(5)
C1 H1C 0.9900
C1 H1D 0.9900
C1 C2 1.513(7)
C2 H2A 1.0000
C2 C3 1.546(6)
C3 H3 1.0000
C3 C4 1.553(6)
C3 C6 1.546(6)
C4 C5 1.524(5)
C4 C9 1.559(6)
C6 H6 1.0000
C6 C7 1.540(7)
C6 C8 1.516(7)
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
N1 H1A 0.9200
N1 H1B 0.9200
N1 C15 1.508(5)
N1 C16 1.502(5)
C10 H10A 0.9900
C10 H10B 0.9900
C10 C11 1.528(6)
C10 C15 1.535(6)
C11 H11A 0.9900
C11 H11B 0.9900
C11 C12 1.525(7)
C12 H12A 0.9900
C12 H12B 0.9900
C12 C13 1.525(7)
C13 H13A 0.9900
C13 H13B 0.9900
C13 C14 1.522(6)
C14 H14A 0.9900
C14 H14B 0.9900
C14 C15 1.519(6)
C15 H15 1.0000
C16 H16 1.0000
C16 C17 1.520(6)
C16 C21 1.532(6)
C17 H17A 0.9900
C17 H17B 0.9900
C17 C18 1.531(6)
C18 H18A 0.9900
C18 H18B 0.9900
C18 C19 1.519(7)
C19 H19A 0.9900
C19 H19B 0.9900
C19 C20 1.521(7)
C20 H20A 0.9900
C20 H20B 0.9900
C20 C21 1.535(6)
C21 H21A 0.9900
C21 H21B 0.9900
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
I1 C1 C2 O1 -178.9(3)
I1 C1 C2 C3 63.3(4)
O1 C2 C3 C4 -21.9(4)
O1 C2 C3 C6 100.3(4)
O2 C4 C5 O1 -137.1(4)
O2 C4 C5 O5 41.5(6)
O2 C4 C9 O3 19.7(5)
O2 C4 C9 O4 -162.7(4)
C1 C2 C3 C4 95.9(4)
C1 C2 C3 C6 -141.9(4)
C2 O1 C5 O5 -177.2(4)
C2 O1 C5 C4 1.4(5)
C2 C3 C4 O2 139.8(4)
C2 C3 C4 C5 22.0(4)
C2 C3 C4 C9 -94.3(4)
C2 C3 C6 C7 -52.7(6)
C2 C3 C6 C8 72.2(5)
C3 C4 C5 O1 -15.4(5)
C3 C4 C5 O5 163.2(5)
C3 C4 C9 O3 -108.2(4)
C3 C4 C9 O4 69.4(5)
C4 C3 C6 C7 63.9(5)
C4 C3 C6 C8 -171.3(4)
C5 O1 C2 C1 -112.6(4)
C5 O1 C2 C3 13.4(5)
C5 C4 C9 O3 139.0(4)
C5 C4 C9 O4 -43.4(5)
C6 C3 C4 O2 18.0(5)
C6 C3 C4 C5 -99.8(4)
C6 C3 C4 C9 143.9(4)
C9 C4 C5 O1 102.3(4)
C9 C4 C5 O5 -79.1(6)
N1 C16 C17 C18 177.6(4)
N1 C16 C21 C20 -174.6(4)
C10 C11 C12 C13 -55.6(6)
C11 C10 C15 N1 -174.1(4)
C11 C10 C15 C14 -54.9(5)
C11 C12 C13 C14 56.0(6)
C12 C13 C14 C15 -55.9(5)
C13 C14 C15 N1 177.1(4)
C13 C14 C15 C10 55.6(5)
C15 N1 C16 C17 -177.2(3)
C15 N1 C16 C21 -53.9(5)
C15 C10 C11 C12 54.7(5)
C16 N1 C15 C10 -59.8(5)
C16 N1 C15 C14 177.5(3)
C16 C17 C18 C19 -56.1(5)
C17 C16 C21 C20 -54.0(5)
C17 C18 C19 C20 57.7(5)
C18 C19 C20 C21 -58.7(5)
C19 C20 C21 C16 56.4(5)
C21 C16 C17 C18 54.6(5)
