#------------------------------------------------------------------------------
#$Date: 2017-11-29 10:00:00 +0200 (Wed, 29 Nov 2017) $
#$Revision: 203756 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/82/1548294.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_1548294
loop_
_publ_author_name
'Pratap S. Patil'
'Ting-Jen Rachel Cheng'
'Medel Manuel L. Zulueta'
'Shih-Ting Yang'
'Larry S. Lico'
'Shang-Cheng Hung'
_publ_section_title
;
 Total synthesis of tetraacylated phosphatidylinositol hexamannoside and
 evaluation of its immunomodulatory activity
;
_journal_name_full               'Nature Communications'
_journal_page_first              7239
_journal_paper_doi               10.1038/ncomms8239
_journal_volume                  6
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C27 H26 O5 S'
_chemical_formula_sum            'C27 H26 O5 S'
_chemical_formula_weight         462.54
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                115.307(2)
_cell_angle_beta                 97.601(2)
_cell_angle_gamma                94.255(2)
_cell_formula_units_Z            1
_cell_length_a                   4.65980(10)
_cell_length_b                   11.2839(3)
_cell_length_c                   12.0321(3)
_cell_measurement_reflns_used    7518
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      31.49
_cell_measurement_theta_min      3.33
_cell_volume                     560.85(3)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10062
_diffrn_reflns_point_group_measured_fraction_full 0.714
_diffrn_reflns_point_group_measured_fraction_max 0.692
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         27.097
_diffrn_reflns_theta_min         1.904
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.9474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_description       niddle
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 847 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3396
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0278
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0198P)²+0.1766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0573
_refine_ls_wR_factor_ref         0.0591
_reflns_number_gt                3188
_reflns_number_total             3396
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ncomms8239-s2.cif
_cod_data_source_block           i14220
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_database_code               1548294
loop_
_symmetry_equiv_pos_as_xyz
'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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.02859(11) 0.72699(6) 0.44237(5) 0.01751(14) Uani 1 d . .
O2 O -0.1567(3) 0.84830(16) 0.78183(15) 0.0148(4) Uani 1 d . .
O3 O 0.2170(3) 0.77669(15) 0.86817(14) 0.0127(3) Uani 1 d . .
O4 O 0.2014(3) 0.47962(16) 0.70746(15) 0.0131(3) Uani 1 d . .
O5 O -0.3113(3) 0.59268(15) 0.53090(14) 0.0130(3) Uani 1 d . .
O6 O -0.0431(3) 0.29578(16) 0.52645(15) 0.0163(4) Uani 1 d . .
C1 C -0.1778(5) 0.7219(2) 0.5602(2) 0.0129(5) Uani 1 d . .
H1 H -0.3389 0.7762 0.5622 0.015 Uiso 1 calc . .
C2 C 0.0221(5) 0.7907(2) 0.6891(2) 0.0132(5) Uani 1 d . .
H2 H 0.167 0.8619 0.6912 0.016 Uiso 1 calc . .
C3 C 0.1826(5) 0.7016(2) 0.7348(2) 0.0126(5) Uani 1 d . .
H3 H 0.379 0.6947 0.7095 0.015 Uiso 1 calc . .
C4 C 0.0122(5) 0.5653(2) 0.6864(2) 0.0124(5) Uani 1 d . .
H4 H -0.1561 0.5698 0.731 0.015 Uiso 1 calc . .
C5 C -0.1010(5) 0.5126(2) 0.5473(2) 0.0130(4) Uani 1 d . .
H5 H 0.0642 0.5171 0.5033 0.016 Uiso 1 calc . .
C6 C -0.2485(5) 0.3707(2) 0.4955(2) 0.0158(5) Uani 1 d . .
H6A H -0.4248 0.3674 0.5325 0.019 Uiso 1 calc . .
H6B H -0.3094 0.333 0.4037 0.019 Uiso 1 calc . .
C7 C 0.0471(5) 0.3481(2) 0.6570(2) 0.0140(5) Uani 1 d . .
H7 H -0.1281 0.3492 0.697 0.017 Uiso 1 calc . .
C8 C 0.2518(5) 0.2646(2) 0.6875(2) 0.0149(5) Uani 1 d . .
C9 C 0.3818(5) 0.3066(2) 0.8110(2) 0.0188(5) Uani 1 d . .
H9 H 0.3428 0.3871 0.8737 0.023 Uiso 1 calc . .
C10 C 0.5696(5) 0.2316(3) 0.8438(2) 0.0219(6) Uani 1 d . .
H10 H 0.6565 0.2604 0.9288 0.026 Uiso 1 calc . .
C11 C 0.6292(6) 0.1150(3) 0.7522(3) 0.0240(6) Uani 1 d . .
H11 H 0.7584 0.064 0.7741 0.029 Uiso 1 calc . .
C12 C 0.5004(6) 0.0733(3) 0.6295(3) 0.0250(6) Uani 1 d . .
H12 H 0.5417 -0.0067 0.5669 0.03 Uiso 1 calc . .
C13 C 0.3100(5) 0.1470(2) 0.5955(2) 0.0194(5) Uani 1 d . .
H13 H 0.2211 0.1171 0.5106 0.023 Uiso 1 calc . .
C14 C -0.0490(5) 0.8303(2) 0.8899(2) 0.0129(5) Uani 1 d . .
H14 H -0.1934 0.7662 0.8987 0.015 Uiso 1 calc . .
C15 C 0.0114(5) 0.9589(2) 1.0071(2) 0.0146(5) Uani 1 d . .
C16 C 0.2071(6) 1.0636(2) 1.0176(2) 0.0217(5) Uani 1 d . .
H16 H 0.3024 1.0549 0.95 0.026 Uiso 1 calc . .
C17 C 0.2628(6) 1.1805(3) 1.1269(3) 0.0283(6) Uani 1 d . .
H17 H 0.3952 1.2526 1.1339 0.034 Uiso 1 calc . .
C18 C 0.1260(6) 1.1933(3) 1.2267(3) 0.0295(7) Uani 1 d . .
H18 H 0.166 1.2735 1.3018 0.035 Uiso 1 calc . .
C19 C -0.0668(6) 1.0895(3) 1.2163(3) 0.0275(6) Uani 1 d . .
H19 H -0.1598 1.0979 1.2844 0.033 Uiso 1 calc . .
C20 C -0.1268(6) 0.9716(3) 1.1060(2) 0.0208(5) Uani 1 d . .
H20 H -0.262 0.9002 1.0986 0.025 Uiso 1 calc . .
C21 C -0.2721(5) 0.6875(2) 0.3192(2) 0.0154(5) Uani 1 d . .
C22 C -0.4040(5) 0.5572(2) 0.2469(2) 0.0172(5) Uani 1 d . .
H22 H -0.3299 0.4879 0.2614 0.021 Uiso 1 calc . .
C23 C -0.6449(5) 0.5283(2) 0.1531(2) 0.0184(5) Uani 1 d . .
H23 H -0.737 0.4391 0.1056 0.022 Uiso 1 calc . .
C24 C -0.7535(5) 0.6271(3) 0.1275(2) 0.0157(5) Uani 1 d . .
C25 C -0.6164(5) 0.7570(3) 0.2001(2) 0.0178(5) Uani 1 d . .
H25 H -0.6876 0.8262 0.1844 0.021 Uiso 1 calc . .
C26 C -0.3787(5) 0.7874(3) 0.2947(2) 0.0164(5) Uani 1 d . .
H26 H -0.2881 0.8767 0.3429 0.02 Uiso 1 calc . .
C27 C -1.0087(5) 0.5945(3) 0.0235(2) 0.0204(5) Uani 1 d . .
H27A H -0.9407 0.6073 -0.0448 0.031 Uiso 1 calc . .
H27B H -1.1545 0.6529 0.0549 0.031 Uiso 1 calc . .
H27C H -1.0971 0.502 -0.0074 0.031 Uiso 1 calc . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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
C21 S C1 98.10(11) . .
C14 O2 C2 108.93(16) . .
C14 O3 C3 105.60(16) . .
C7 O4 C4 109.89(16) . .
C1 O5 C5 111.79(16) . .
C7 O6 C6 111.01(17) . .
O5 C1 C2 113.49(19) . .
O5 C1 S 113.18(15) . .
C2 C1 S 108.82(15) . .
O5 C1 H1 107 . .
C2 C1 H1 107 . .
S C1 H1 107 . .
O2 C2 C3 102.71(17) . .
O2 C2 C1 108.32(18) . .
C3 C2 C1 116.74(19) . .
O2 C2 H2 109.6 . .
C3 C2 H2 109.6 . .
C1 C2 H2 109.6 . .
O3 C3 C4 113.08(18) . .
O3 C3 C2 101.41(16) . .
C4 C3 C2 112.57(18) . .
O3 C3 H3 109.8 . .
C4 C3 H3 109.8 . .
C2 C3 H3 109.8 . .
O4 C4 C3 109.04(17) . .
O4 C4 C5 109.55(17) . .
C3 C4 C5 109.11(17) . .
O4 C4 H4 109.7 . .
C3 C4 H4 109.7 . .
C5 C4 H4 109.7 . .
O5 C5 C6 109.23(18) . .
O5 C5 C4 107.88(17) . .
C6 C5 C4 109.42(18) . .
O5 C5 H5 110.1 . .
C6 C5 H5 110.1 . .
C4 C5 H5 110.1 . .
O6 C6 C5 108.10(18) . .
O6 C6 H6A 110.1 . .
C5 C6 H6A 110.1 . .
O6 C6 H6B 110.1 . .
C5 C6 H6B 110.1 . .
H6A C6 H6B 108.4 . .
O6 C7 O4 110.99(18) . .
O6 C7 C8 110.11(18) . .
O4 C7 C8 107.41(18) . .
O6 C7 H7 109.4 . .
O4 C7 H7 109.4 . .
C8 C7 H7 109.4 . .
C9 C8 C13 119.8(2) . .
C9 C8 C7 118.4(2) . .
C13 C8 C7 121.8(2) . .
C8 C9 C10 120.4(2) . .
C8 C9 H9 119.8 . .
C10 C9 H9 119.8 . .
C11 C10 C9 119.8(2) . .
C11 C10 H10 120.1 . .
C9 C10 H10 120.1 . .
C12 C11 C10 119.7(2) . .
C12 C11 H11 120.1 . .
C10 C11 H11 120.1 . .
C11 C12 C13 121.0(2) . .
C11 C12 H12 119.5 . .
C13 C12 H12 119.5 . .
C8 C13 C12 119.3(2) . .
C8 C13 H13 120.4 . .
C12 C13 H13 120.4 . .
O3 C14 O2 106.06(16) . .
O3 C14 C15 109.45(18) . .
O2 C14 C15 111.95(18) . .
O3 C14 H14 109.8 . .
O2 C14 H14 109.8 . .
C15 C14 H14 109.8 . .
C20 C15 C16 120.0(2) . .
C20 C15 C14 119.4(2) . .
C16 C15 C14 120.6(2) . .
C17 C16 C15 119.7(2) . .
C17 C16 H16 120.1 . .
C15 C16 H16 120.1 . .
C16 C17 C18 120.4(3) . .
C16 C17 H17 119.8 . .
C18 C17 H17 119.8 . .
C19 C18 C17 119.8(3) . .
C19 C18 H18 120.1 . .
C17 C18 H18 120.1 . .
C18 C19 C20 120.2(3) . .
C18 C19 H19 119.9 . .
C20 C19 H19 119.9 . .
C15 C20 C19 119.8(3) . .
C15 C20 H20 120.1 . .
C19 C20 H20 120.1 . .
C22 C21 C26 119.3(2) . .
C22 C21 S 120.57(18) . .
C26 C21 S 120.10(19) . .
C21 C22 C23 119.9(2) . .
C21 C22 H22 120 . .
C23 C22 H22 120 . .
C24 C23 C22 121.3(2) . .
C24 C23 H23 119.3 . .
C22 C23 H23 119.3 . .
C23 C24 C25 117.9(2) . .
C23 C24 C27 121.0(2) . .
C25 C24 C27 121.0(2) . .
C26 C25 C24 121.3(2) . .
C26 C25 H25 119.3 . .
C24 C25 H25 119.3 . .
C25 C26 C21 120.1(2) . .
C25 C26 H26 119.9 . .
C21 C26 H26 119.9 . .
C24 C27 H27A 109.5 . .
C24 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
C24 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S C21 1.776(2) .
S C1 1.833(2) .
O2 C14 1.432(3) .
O2 C2 1.438(3) .
O3 C14 1.425(3) .
O3 C3 1.438(3) .
O4 C7 1.430(3) .
O4 C4 1.433(3) .
O5 C1 1.416(3) .
O5 C5 1.431(3) .
O6 C7 1.410(3) .
O6 C6 1.437(3) .
C1 C2 1.535(3) .
C1 H1 1 .
C2 C3 1.532(3) .
C2 H2 1 .
C3 C4 1.506(3) .
C3 H3 1 .
C4 C5 1.517(3) .
C4 H4 1 .
C5 C6 1.515(3) .
C5 H5 1 .
C6 H6A 0.99 .
C6 H6B 0.99 .
C7 C8 1.506(3) .
C7 H7 1 .
C8 C9 1.384(3) .
C8 C13 1.391(3) .
C9 C10 1.394(3) .
C9 H9 0.95 .
C10 C11 1.385(4) .
C10 H10 0.95 .
C11 C12 1.376(4) .
C11 H11 0.95 .
C12 C13 1.396(3) .
C12 H12 0.95 .
C13 H13 0.95 .
C14 C15 1.503(3) .
C14 H14 1 .
C15 C20 1.386(3) .
C15 C16 1.387(3) .
C16 C17 1.383(4) .
C16 H16 0.95 .
C17 C18 1.391(4) .
C17 H17 0.95 .
C18 C19 1.372(4) .
C18 H18 0.95 .
C19 C20 1.395(4) .
C19 H19 0.95 .
C20 H20 0.95 .
C21 C22 1.388(3) .
C21 C26 1.390(3) .
C22 C23 1.391(3) .
C22 H22 0.95 .
C23 C24 1.389(3) .
C23 H23 0.95 .
C24 C25 1.393(4) .
C24 C27 1.505(3) .
C25 C26 1.384(3) .
C25 H25 0.95 .
C26 H26 0.95 .
C27 H27A 0.98 .
C27 H27B 0.98 .
C27 H27C 0.98 .
