#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/29/2222907.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222907
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Liew, Wei-Ching'
'Rai, Sankappa'
'Shetty, Prakash'
'Isloor, Arun M.'
_publ_section_title
;An orthorhombic polymorph of
 6-deoxy-6-iodo-1,2:3,4-di-O-isopropylidene-α-<small>D</small>-galactopyranoside
;
_journal_coeditor_code           TK2509
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1999
_journal_page_last               o2000
_journal_paper_doi               10.1107/S1600536809029031
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H19 I O5'
_chemical_formula_moiety         'C12 H19 I O5'
_chemical_formula_sum            'C12 H19 I O5'
_chemical_formula_weight         370.17
_chemical_name_systematic
;
6-deoxy-6-iodo-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.35950(10)
_cell_length_b                   11.5145(2)
_cell_length_c                   16.9945(2)
_cell_measurement_reflns_used    6517
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      3.0
_cell_volume                     1440.13(4)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω'
_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  0.046
_diffrn_reflns_av_sigmaI/netI    0.050
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            27359
_diffrn_reflns_theta_full        37.5
_diffrn_reflns_theta_max         37.5
_diffrn_reflns_theta_min         2.1
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.234
_exptl_absorpt_correction_T_max  0.785
_exptl_absorpt_correction_T_min  0.703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.87
_refine_diff_density_min         -1.24
_refine_ls_abs_structure_details 'Flack (1983), 3286 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.020(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         7509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.048
_refine_ls_R_factor_gt           0.035
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0418P)²+0.1348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.074
_refine_ls_wR_factor_ref         0.096
_reflns_number_gt                6211
_reflns_number_total             7509
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2509.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2222907
_cod_database_fobs_code          2222907
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.48767(2) -0.062287(16) 0.585388(10) 0.02322(5) Uani d . 1 . .
O O1 0.3941(3) 0.30650(19) 0.54871(11) 0.0202(4) Uani d . 1 . .
O O2 0.4126(2) 0.41053(17) 0.66190(11) 0.0174(4) Uani d . 1 . .
O O3 -0.0095(3) 0.31453(16) 0.74636(10) 0.0169(3) Uani d . 1 . .
O O4 0.0869(3) 0.13209(18) 0.77122(12) 0.0181(4) Uani d . 1 . .
O O5 0.2158(2) 0.16776(16) 0.61095(11) 0.0162(3) Uani d . 1 . .
C C1 0.2269(3) 0.2856(2) 0.58845(16) 0.0166(4) Uani d . 1 . .
H H1A 0.1256 0.3041 0.5532 0.020 Uiso calc R 1 . .
C C2 0.4873(3) 0.4031(2) 0.58404(14) 0.0167(4) Uani d . 1 . .
C C3 0.2281(3) 0.3722(2) 0.65788(15) 0.0166(4) Uani d . 1 . .
H H3A 0.1476 0.4379 0.6466 0.020 Uiso calc R 1 . .
C C4 0.1835(3) 0.3209(3) 0.73797(15) 0.0167(4) Uani d . 1 . .
H H4A 0.2335 0.3710 0.7793 0.020 Uiso calc R 1 . .
C C5 -0.0464(3) 0.2160(2) 0.79401(15) 0.0165(4) Uani d . 1 . .
C C6 0.2485(3) 0.1941(2) 0.75132(13) 0.0152(5) Uani d . 1 . .
H H6A 0.3359 0.1907 0.7948 0.018 Uiso calc R 1 . .
C C7 0.3309(3) 0.1412(2) 0.67660(15) 0.0165(5) Uani d . 1 . .
H H7A 0.4522 0.1737 0.6677 0.020 Uiso calc R 1 . .
C C8 0.3433(4) 0.0106(3) 0.68407(16) 0.0194(5) Uani d . 1 . .
H H8A 0.2220 -0.0221 0.6864 0.023 Uiso calc R 1 . .
H H8B 0.4059 -0.0092 0.7325 0.023 Uiso calc R 1 . .
C C9 0.4481(4) 0.5139(3) 0.53734(17) 0.0235(6) Uani d . 1 . .
H H9A 0.3193 0.5267 0.5353 0.035 Uiso calc R 1 . .
H H9B 0.4945 0.5057 0.4848 0.035 Uiso calc R 1 . .
H H9C 0.5058 0.5787 0.5626 0.035 Uiso calc R 1 . .
C C10 0.6874(4) 0.3785(3) 0.59115(18) 0.0220(5) Uani d . 1 . .
H H10A 0.7049 0.3032 0.6142 0.033 Uiso calc R 1 . .
H H10B 0.7430 0.4364 0.6240 0.033 Uiso calc R 1 . .
H H10C 0.7421 0.3804 0.5399 0.033 Uiso calc R 1 . .
C C11 -0.0254(4) 0.2444(3) 0.88146(15) 0.0241(5) Uani d . 1 . .
H H11A 0.0946 0.2739 0.8910 0.036 Uiso calc R 1 . .
H H11B -0.0440 0.1753 0.9120 0.036 Uiso calc R 1 . .
H H11C -0.1136 0.3018 0.8963 0.036 Uiso calc R 1 . .
C C12 -0.2321(4) 0.1723(3) 0.77260(18) 0.0205(5) Uani d . 1 . .
H H12A -0.2307 0.1435 0.7196 0.031 Uiso calc R 1 . .
H H12B -0.3183 0.2346 0.7766 0.031 Uiso calc R 1 . .
H H12C -0.2662 0.1109 0.8078 0.031 Uiso calc R 1 . .
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'
I I -0.4742 1.8119 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C2 . . 110.17(19) ?
C3 O2 C2 . . 107.52(19) ?
C5 O3 C4 . . 106.8(2) ?
C6 O4 C5 . . 107.3(2) ?
C1 O5 C7 . . 112.42(19) ?
O5 C1 O1 . . 109.9(2) ?
O5 C1 C3 . . 114.4(2) ?
O1 C1 C3 . . 104.4(2) ?
O5 C1 H1A . . 109.3 ?
O1 C1 H1A . . 109.3 ?
C3 C1 H1A . . 109.3 ?
O2 C2 O1 . . 104.41(18) ?
O2 C2 C10 . . 108.2(2) ?
O1 C2 C10 . . 110.8(2) ?
O2 C2 C9 . . 110.8(2) ?
O1 C2 C9 . . 109.8(2) ?
C10 C2 C9 . . 112.5(2) ?
O2 C3 C4 . . 106.4(2) ?
O2 C3 C1 . . 104.0(2) ?
C4 C3 C1 . . 115.6(2) ?
O2 C3 H3A . . 110.2 ?
C4 C3 H3A . . 110.2 ?
C1 C3 H3A . . 110.2 ?
O3 C4 C3 . . 108.9(2) ?
O3 C4 C6 . . 104.1(2) ?
C3 C4 C6 . . 115.4(2) ?
O3 C4 H4A . . 109.4 ?
C3 C4 H4A . . 109.4 ?
C6 C4 H4A . . 109.4 ?
O3 C5 O4 . . 104.70(19) ?
O3 C5 C12 . . 107.7(2) ?
O4 C5 C12 . . 109.4(2) ?
O3 C5 C11 . . 111.4(2) ?
O4 C5 C11 . . 109.8(2) ?
C12 C5 C11 . . 113.5(2) ?
O4 C6 C7 . . 109.1(2) ?
O4 C6 C4 . . 104.4(2) ?
C7 C6 C4 . . 112.0(2) ?
O4 C6 H6A . . 110.4 ?
C7 C6 H6A . . 110.4 ?
C4 C6 H6A . . 110.4 ?
O5 C7 C8 . . 108.2(2) ?
O5 C7 C6 . . 109.1(2) ?
C8 C7 C6 . . 110.4(2) ?
O5 C7 H7A . . 109.7 ?
C8 C7 H7A . . 109.7 ?
C6 C7 H7A . . 109.7 ?
C7 C8 I1 . . 110.61(18) ?
C7 C8 H8A . . 109.5 ?
I1 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
I1 C8 H8B . . 109.5 ?
H8A C8 H8B . . 108.1 ?
C2 C9 H9A . . 109.5 ?
C2 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C2 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C2 C10 H10A . . 109.5 ?
C2 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C2 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C5 C11 H11A . . 109.5 ?
C5 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C5 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C5 C12 H12A . . 109.5 ?
C5 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C5 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 C8 . 2.155(3) ?
O1 C1 . 1.424(3) ?
O1 C2 . 1.438(3) ?
O2 C3 . 1.430(3) ?
O2 C2 . 1.435(3) ?
O3 C5 . 1.420(3) ?
O3 C4 . 1.429(3) ?
O4 C6 . 1.428(3) ?
O4 C5 . 1.431(3) ?
O5 C1 . 1.412(3) ?
O5 C7 . 1.434(3) ?
C1 C3 . 1.545(4) ?
C1 H1A . 0.9800 ?
C2 C10 . 1.505(4) ?
C2 C9 . 1.530(4) ?
C3 C4 . 1.519(4) ?
C3 H3A . 0.9800 ?
C4 C6 . 1.554(4) ?
C4 H4A . 0.9800 ?
C5 C12 . 1.501(4) ?
C5 C11 . 1.530(4) ?
C6 C7 . 1.533(4) ?
C6 H6A . 0.9800 ?
C7 C8 . 1.512(4) ?
C7 H7A . 0.9800 ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C8 H8B O2 4_646 0.97 2.42 3.377(3) 169 yes
C12 H12C O2 4_546 0.96 2.60 3.477(4) 152 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8582260
