#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:28:12 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180140 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/37/7103731.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_7103731
loop_
_publ_author_name
P.Clarke
M.Ebden
M.Grist
C.Wilson
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/b303706a
_journal_year                    2003
_chemical_formula_sum            'C15 H25 I O5'
_chemical_formula_weight         412.25
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   'geometrically placed, OH from delta-F'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                65.415(1)
_cell_angle_beta                 77.402(1)
_cell_angle_gamma                81.897(1)
_cell_formula_units_Z            2
_cell_length_a                   6.5249(5)
_cell_length_b                   11.3828(9)
_cell_length_c                   13.3018(10)
_cell_measurement_reflns_used    4648
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.1
_cell_volume                     875.35(12)
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2002)'
_computing_data_collection       'Bruker SMART version 5.624 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_publication_material  'SHELXL-97; PLATON (Spek, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker SMART1000 CCD area detector'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7666
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.71
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.846
_exptl_absorpt_correction_T_max  0.831
_exptl_absorpt_correction_T_min  0.530
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker Shelxtl v6.12'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.477
_refine_diff_density_min         -1.170
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    'riding model, OH rigid rotors'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3876
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0287P)²+1.4585P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0814
_reflns_number_gt                3298
_reflns_number_total             3876
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b303706a.txt
_cod_data_source_block           ibutac
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7103731
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.85878(4) -0.15680(2) 0.96012(2) 0.05959(11) Uani 1 1 d . . .
O1 O 0.7066(3) 0.37554(17) 0.57290(17) 0.0295(4) Uani 1 1 d . . .
H1 H 0.5945 0.3521 0.5675 0.035 Uiso 1 1 calc R . .
O2 O 0.8019(3) 0.16423(17) 0.63849(16) 0.0274(4) Uani 1 1 d . . .
O3 O 1.3458(3) 0.35862(19) 0.5226(2) 0.0377(5) Uani 1 1 d . . .
H3 H 1.3116 0.4378 0.4917 0.045 Uiso 1 1 calc R . .
O4 O 0.7211(4) 0.3811(3) 0.8637(2) 0.0558(7) Uani 1 1 d . . .
O5 O 0.4516(3) 0.4433(2) 0.7669(2) 0.0405(5) Uani 1 1 d . . .
C1 C 0.7908(4) 0.2778(2) 0.6615(2) 0.0263(5) Uani 1 1 d . . .
C2 C 1.0100(4) 0.3196(2) 0.6514(2) 0.0284(6) Uani 1 1 d . . .
H2A H 1.0048 0.4141 0.6308 0.034 Uiso 1 1 calc R . .
H2B H 1.0587 0.2749 0.7243 0.034 Uiso 1 1 calc R . .
C3 C 1.1613(4) 0.2855(3) 0.5618(2) 0.0293(6) Uani 1 1 d . . .
H3A H 1.0887 0.3070 0.4969 0.035 Uiso 1 1 calc R . .
C4 C 1.2394(4) 0.1418(3) 0.6023(3) 0.0342(6) Uani 1 1 d . . .
H4A H 1.2310 0.1104 0.5443 0.041 Uiso 1 1 calc R . .
H4B H 1.3895 0.1356 0.6083 0.041 Uiso 1 1 calc R . .
C5 C 1.1205(4) 0.0516(3) 0.7146(3) 0.0324(6) Uani 1 1 d . . .
H5A H 1.1312 0.0814 0.7733 0.039 Uiso 1 1 calc R . .
H5B H 1.1896 -0.0364 0.7345 0.039 Uiso 1 1 calc R . .
C6 C 0.8864(4) 0.0437(2) 0.7156(2) 0.0306(6) Uani 1 1 d . . .
C7 C 0.7458(5) 0.0167(3) 0.8308(3) 0.0385(7) Uani 1 1 d . . .
H7A H 0.6026 0.0009 0.8252 0.046 Uiso 1 1 calc R . .
C8 C 0.7220(5) 0.1289(3) 0.8665(3) 0.0414(7) Uani 1 1 d . . .
H8A H 0.8593 0.1435 0.8783 0.050 Uiso 1 1 calc R . .
H8B H 0.6212 0.1087 0.9381 0.050 Uiso 1 1 calc R . .
C9 C 0.6419(5) 0.2510(3) 0.7748(2) 0.0328(6) Uani 1 1 d . . .
H9A H 0.5011 0.2342 0.7669 0.039 Uiso 1 1 calc R . .
C10 C 0.6133(5) 0.3656(3) 0.8083(3) 0.0383(7) Uani 1 1 d . . .
C11 C 0.3779(5) 0.5607(3) 0.7900(3) 0.0450(8) Uani 1 1 d . . .
C12 C 0.2128(7) 0.6216(4) 0.7153(5) 0.0771(14) Uani 1 1 d . . .
H12A H 0.0997 0.5624 0.7392 0.116 Uiso 1 1 calc R . .
H12B H 0.2776 0.6386 0.6371 0.116 Uiso 1 1 calc R . .
H12C H 0.1548 0.7032 0.7213 0.116 Uiso 1 1 calc R . .
C13 C 0.2830(7) 0.5185(4) 0.9126(4) 0.0698(13) Uani 1 1 d . . .
H13A H 0.3940 0.4798 0.9578 0.105 Uiso 1 1 calc R . .
H13B H 0.1789 0.4545 0.9328 0.105 Uiso 1 1 calc R . .
H13C H 0.2144 0.5936 0.9270 0.105 Uiso 1 1 calc R . .
C14 C 0.5541(6) 0.6502(3) 0.7545(4) 0.0587(10) Uani 1 1 d . . .
H14A H 0.6590 0.6097 0.8035 0.088 Uiso 1 1 calc R . .
H14B H 0.4975 0.7320 0.7605 0.088 Uiso 1 1 calc R . .
H14C H 0.6203 0.6672 0.6766 0.088 Uiso 1 1 calc R . .
C15 C 0.8582(5) -0.0534(3) 0.6692(3) 0.0417(7) Uani 1 1 d . . .
H15A H 0.7083 -0.0568 0.6706 0.063 Uiso 1 1 calc R . .
H15B H 0.9137 -0.1392 0.7154 0.063 Uiso 1 1 calc R . .
H15C H 0.9343 -0.0269 0.5917 0.063 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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C6 118.3(2) . . ?
C10 O5 C11 122.1(3) . . ?
O1 C1 O2 104.3(2) . . ?
O1 C1 C2 105.1(2) . . ?
O2 C1 C2 111.7(2) . . ?
O1 C1 C9 111.7(2) . . ?
O2 C1 C9 107.0(2) . . ?
C2 C1 C9 116.5(2) . . ?
C3 C2 C1 109.1(2) . . ?
O3 C3 C2 111.0(2) . . ?
O3 C3 C4 106.3(2) . . ?
C2 C3 C4 113.9(2) . . ?
C5 C4 C3 115.7(2) . . ?
C4 C5 C6 114.3(2) . . ?
O2 C6 C15 103.1(2) . . ?
O2 C6 C7 106.0(2) . . ?
C15 C6 C7 111.4(2) . . ?
O2 C6 C5 111.1(2) . . ?
C15 C6 C5 110.9(2) . . ?
C7 C6 C5 113.8(3) . . ?
C8 C7 C6 113.5(2) . . ?
C8 C7 I1 109.6(2) . . ?
C6 C7 I1 111.31(18) . . ?
C7 C8 C9 109.2(3) . . ?
C10 C9 C8 110.8(3) . . ?
C10 C9 C1 112.3(2) . . ?
C8 C9 C1 110.0(2) . . ?
O4 C10 O5 126.6(3) . . ?
O4 C10 C9 124.1(3) . . ?
O5 C10 C9 109.3(3) . . ?
O5 C11 C13 108.4(3) . . ?
O5 C11 C14 111.1(3) . . ?
C13 C11 C14 112.7(4) . . ?
O5 C11 C12 101.7(3) . . ?
C13 C11 C12 111.9(4) . . ?
C14 C11 C12 110.5(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C7 2.172(3) . ?
O1 C1 1.395(3) . ?
O2 C1 1.437(3) . ?
O2 C6 1.449(3) . ?
O3 C3 1.436(3) . ?
O4 C10 1.199(4) . ?
O5 C10 1.335(4) . ?
O5 C11 1.486(3) . ?
C1 C2 1.531(4) . ?
C1 C9 1.540(4) . ?
C2 C3 1.520(4) . ?
C3 C4 1.542(4) . ?
C4 C5 1.527(4) . ?
C5 C6 1.540(4) . ?
C6 C15 1.520(4) . ?
C6 C7 1.536(4) . ?
C7 C8 1.515(4) . ?
C8 C9 1.534(4) . ?
C9 C10 1.521(4) . ?
C11 C13 1.505(5) . ?
C11 C14 1.509(5) . ?
C11 C12 1.520(6) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O3 0.84 1.83 2.636(3) 160.5 1_455
O3 H3 O1 0.84 1.93 2.754(3) 167.1 2_766
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 O2 C1 O1 179.3(2) . . . . ?
C6 O2 C1 C2 66.3(3) . . . . ?
C6 O2 C1 C9 -62.2(3) . . . . ?
O1 C1 C2 C3 -80.4(2) . . . . ?
O2 C1 C2 C3 32.1(3) . . . . ?
C9 C1 C2 C3 155.4(2) . . . . ?
C1 C2 C3 O3 160.7(2) . . . . ?
C1 C2 C3 C4 -79.3(3) . . . . ?
O3 C3 C4 C5 135.2(3) . . . . ?
C2 C3 C4 C5 12.7(4) . . . . ?
C3 C4 C5 C6 62.2(3) . . . . ?
C1 O2 C6 C15 176.0(2) . . . . ?
C1 O2 C6 C7 58.9(3) . . . . ?
C1 O2 C6 C5 -65.1(3) . . . . ?
C4 C5 C6 O2 -30.2(3) . . . . ?
C4 C5 C6 C15 83.8(3) . . . . ?
C4 C5 C6 C7 -149.8(2) . . . . ?
O2 C6 C7 C8 -53.0(3) . . . . ?
C15 C6 C7 C8 -164.3(3) . . . . ?
C5 C6 C7 C8 69.4(3) . . . . ?
O2 C6 C7 I1 -177.10(17) . . . . ?
C15 C6 C7 I1 71.5(3) . . . . ?
C5 C6 C7 I1 -54.7(3) . . . . ?
C6 C7 C8 C9 55.0(3) . . . . ?
I1 C7 C8 C9 -179.9(2) . . . . ?
C7 C8 C9 C10 179.3(3) . . . . ?
C7 C8 C9 C1 -55.9(3) . . . . ?
O1 C1 C9 C10 -65.5(3) . . . . ?
O2 C1 C9 C10 -179.0(2) . . . . ?
C2 C1 C9 C10 55.3(3) . . . . ?
O1 C1 C9 C8 170.6(2) . . . . ?
O2 C1 C9 C8 57.0(3) . . . . ?
C2 C1 C9 C8 -68.6(3) . . . . ?
C11 O5 C10 O4 -2.7(5) . . . . ?
C11 O5 C10 C9 177.0(2) . . . . ?
C8 C9 C10 O4 32.8(4) . . . . ?
C1 C9 C10 O4 -90.7(4) . . . . ?
C8 C9 C10 O5 -146.9(3) . . . . ?
C1 C9 C10 O5 89.6(3) . . . . ?
C10 O5 C11 C13 -68.1(4) . . . . ?
C10 O5 C11 C14 56.3(4) . . . . ?
C10 O5 C11 C12 173.8(3) . . . . ?
