#------------------------------------------------------------------------------
#$Date: 2017-10-13 00:32:00 +0100 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/78/1507820.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_1507820
loop_
_publ_author_name
'Tian, Jun'
'Gao, Wen-Chao'
'Zhou, Dong-Mei'
'Zhang, Chi'
_publ_section_title
;
 Recyclable hypervalent iodine(III) reagent iodosodilactone as an
 efficient coupling reagent for direct esterification, amidation, and
 peptide coupling.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3020
_journal_page_last               3023
_journal_paper_doi               10.1021/ol301085v
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C8 H3 I O4'
_chemical_formula_sum            'C8 H3 I O4'
_chemical_formula_weight         290.00
_chemical_name_common            iodosodilactone
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.88(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.447(3)
_cell_length_b                   8.1328(16)
_cell_length_c                   6.7939(14)
_cell_measurement_reflns_used    1981
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.5
_cell_volume                     734.1(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear(Rigaku/MSC Inc., 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Rigaku Saturn CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0507
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4686
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.85
_diffrn_reflns_theta_min         1.53
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.334
_exptl_absorpt_correction_T_max  0.6711
_exptl_absorpt_correction_T_min  0.3987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.624
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         2.061
_refine_diff_density_min         -1.406
_refine_diff_density_rms         0.318
_refine_ls_extinction_coef       0.0316(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0307
_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^)+(0.0529P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.0962
_reflns_number_gt                1416
_reflns_number_total             1716
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301085v_si_002.cif
_cod_data_source_block           r90717a1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 1891 2012-01-12 08:04:46Z andrius 

 Adding full bibliography for 1507820.cif.

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scans' was replaced
with the value 'multi-scan' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1507820
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
I1 I 0.38158(2) 0.42328(4) 0.15108(5) 0.01072(18) Uani 1 1 d .
O4 O 0.4115(3) 0.9299(4) 0.1816(6) 0.0158(9) Uani 1 1 d .
C7 C 0.1774(4) 0.3145(6) -0.0373(8) 0.0135(11) Uani 1 1 d .
O2 O 0.1081(3) 0.2288(5) -0.1086(6) 0.0187(9) Uani 1 1 d .
C3 C 0.0949(4) 0.6023(6) -0.1018(8) 0.0123(11) Uani 1 1 d .
H3 H 0.0317 0.5576 -0.1589 0.015 Uiso 1 1 calc R
O3 O 0.4448(3) 0.6635(4) 0.2070(5) 0.0149(8) Uani 1 1 d .
O1 O 0.2662(3) 0.2516(4) 0.0466(5) 0.0144(8) Uani 1 1 d .
C5 C 0.1988(4) 0.8431(6) -0.0062(7) 0.0117(10) Uani 1 1 d .
H5 H 0.2057 0.9592 0.0025 0.014 Uiso 1 1 calc R
C6 C 0.2801(4) 0.7401(6) 0.0606(7) 0.0110(10) Uani 1 1 d .
C1 C 0.2640(4) 0.5738(6) 0.0452(7) 0.0104(11) Uani 1 1 d .
C4 C 0.1080(4) 0.7723(6) -0.0853(7) 0.0125(10) Uani 1 1 d .
H4 H 0.0524 0.8419 -0.1301 0.015 Uiso 1 1 calc R
C8 C 0.3837(4) 0.7867(7) 0.1538(6) 0.0101(11) Uani 1 1 d .
C2 C 0.1753(4) 0.4994(6) -0.0337(7) 0.0104(10) Uani 1 1 d .
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
I1 0.0111(2) 0.0079(3) 0.0122(2) 0.00071(12) -0.00122(13) 0.00060(12)
O4 0.014(2) 0.011(2) 0.021(2) -0.0010(14) -0.0022(16) -0.0020(14)
C7 0.016(3) 0.011(3) 0.013(2) 0.000(2) 0.002(2) 0.001(2)
O2 0.017(2) 0.012(2) 0.025(2) -0.0031(16) -0.0025(16) -0.0054(15)
C3 0.011(2) 0.015(3) 0.011(2) 0.001(2) 0.001(2) 0.001(2)
O3 0.016(2) 0.006(2) 0.0219(19) -0.0001(15) 0.0000(15) -0.0009(15)
O1 0.0154(19) 0.0050(19) 0.0208(18) -0.0004(15) -0.0035(15) -0.0001(14)
C5 0.023(3) 0.003(3) 0.010(2) 0.0008(19) 0.005(2) 0.000(2)
C6 0.014(3) 0.010(3) 0.009(2) -0.0004(19) 0.0028(19) -0.001(2)
C1 0.009(2) 0.015(3) 0.007(2) 0.0008(18) 0.0003(19) 0.0040(19)
C4 0.014(3) 0.012(3) 0.012(2) 0.004(2) 0.0023(19) 0.006(2)
C8 0.010(2) 0.015(3) 0.005(2) 0.0004(19) 0.0001(18) 0.002(2)
C2 0.013(3) 0.008(3) 0.010(2) -0.0013(19) 0.0005(19) -0.0005(19)
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'
I I -0.4742 1.8119 '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
C1 I1 O1 77.91(19)
C1 I1 O3 77.30(17)
O1 I1 O3 155.21(14)
O2 C7 O1 122.2(5)
O2 C7 C2 124.8(5)
O1 C7 C2 113.0(4)
C2 C3 C4 119.2(5)
C2 C3 H3 120.4
C4 C3 H3 120.4
C8 O3 I1 115.7(3)
C7 O1 I1 116.6(3)
C4 C5 C6 118.5(5)
C4 C5 H5 120.8
C6 C5 H5 120.8
C1 C6 C5 117.4(5)
C1 C6 C8 114.2(5)
C5 C6 C8 128.4(5)
C2 C1 C6 125.7(5)
C2 C1 I1 116.9(4)
C6 C1 I1 117.4(4)
C5 C4 C3 122.5(5)
C5 C4 H4 118.7
C3 C4 H4 118.7
O4 C8 O3 121.3(5)
O4 C8 C6 123.3(5)
O3 C8 C6 115.4(5)
C1 C2 C3 116.7(5)
C1 C2 C7 115.5(5)
C3 C2 C7 127.8(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C1 2.041(5)
I1 O1 2.126(4)
I1 O3 2.141(4)
O4 C8 1.229(6)
C7 O2 1.204(6)
C7 O1 1.343(6)
C7 C2 1.504(7)
C3 C2 1.389(7)
C3 C4 1.396(7)
C3 H3 0.9500
O3 C8 1.311(6)
C5 C4 1.381(7)
C5 C6 1.396(7)
C5 H5 0.9500
C6 C1 1.371(7)
C6 C8 1.487(7)
C1 C2 1.370(7)
C4 H4 0.9500
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
C1 I1 O3 C8 0.6(3)
O1 I1 O3 C8 1.3(5)
O2 C7 O1 I1 177.0(4)
C2 C7 O1 I1 -2.3(5)
C1 I1 O1 C7 1.2(4)
O3 I1 O1 C7 0.5(5)
C4 C5 C6 C1 -0.7(7)
C4 C5 C6 C8 -178.8(4)
C5 C6 C1 C2 1.3(8)
C8 C6 C1 C2 179.7(5)
C5 C6 C1 I1 -178.1(3)
C8 C6 C1 I1 0.3(6)
O1 I1 C1 C2 0.4(4)
O3 I1 C1 C2 -179.9(4)
O1 I1 C1 C6 179.8(4)
O3 I1 C1 C6 -0.5(4)
C6 C5 C4 C3 -0.4(7)
C2 C3 C4 C5 1.0(8)
I1 O3 C8 O4 178.9(4)
I1 O3 C8 C6 -0.7(5)
C1 C6 C8 O4 -179.2(5)
C5 C6 C8 O4 -1.1(8)
C1 C6 C8 O3 0.3(6)
C5 C6 C8 O3 178.4(4)
C6 C1 C2 C3 -0.7(8)
I1 C1 C2 C3 178.7(4)
C6 C1 C2 C7 178.9(5)
I1 C1 C2 C7 -1.7(6)
C4 C3 C2 C1 -0.5(7)
C4 C3 C2 C7 180.0(5)
O2 C7 C2 C1 -176.6(5)
O1 C7 C2 C1 2.6(6)
O2 C7 C2 C3 2.9(8)
O1 C7 C2 C3 -177.8(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28282178