#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/32/7103261.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_7103261
loop_
_publ_author_name
'Liu, Xinyu'
'Wada, Reiko'
'Boonyarattanakalin, Siwarutt'
'Castagner, Bastien'
'Seeberger, Peter H'
_publ_section_title
;
 Automated synthesis of lipomannan backbone alpha(1-6) oligomannoside
 via glycosyl phosphates: glycosyl tricyclic orthoesters revisited.
;
_journal_issue                   30
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3510
_journal_page_last               3512
_journal_paper_doi               10.1039/b804069a
_journal_year                    2008
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C27 H26 O6'
_chemical_formula_sum            'C27 H26 O6'
_chemical_formula_weight         446.48
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 107.452(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.9274(6)
_cell_length_b                   9.4363(7)
_cell_length_c                   12.4041(8)
_cell_measurement_reflns_used    8364
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.98
_cell_measurement_theta_min      3.17
_cell_volume                     1108.50(13)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Kappa CCD'
_computing_data_reduction        'Denzo + Scalepak (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP (Johnson,1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et Al., 1997)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0614
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3686
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Cut fragment'
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_coef       0.095(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         2248
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0496P)²+0.2717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                2019
_reflns_number_total             2248
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b804069a.txt
_cod_data_source_block           xliu1_seeber_06
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7103261
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2313(3) 0.5402(3) 0.7217(2) 0.0314(6) Uani 1 d . . .
O2 O 0.34137(19) 0.5894(2) 0.68228(16) 0.0339(5) Uani 1 d . . .
C3 C 0.4329(3) 0.6740(3) 0.7688(2) 0.0324(6) Uani 1 d . . .
H3A H 0.5329 0.6585 0.7697 0.028(7) Uiso 1 calc R . .
C4 C 0.4121(3) 0.6156(3) 0.8785(2) 0.0318(6) Uani 1 d . . .
H4A H 0.4969 0.5595 0.9210 0.045(9) Uiso 1 calc R . .
O5 O 0.29107(19) 0.5238(2) 0.84074(16) 0.0335(5) Uani 1 d . . .
O6 O 0.11819(19) 0.6360(2) 0.69912(17) 0.0352(5) Uani 1 d . . .
C7 C 0.1434(3) 0.7815(3) 0.6777(2) 0.0352(6) Uani 1 d . . .
H7A H 0.0557 0.8357 0.6702 0.029(7) Uiso 1 calc R . .
H7B H 0.1633 0.7869 0.6042 0.043(9) Uiso 1 calc R . .
C8 C 0.2637(3) 0.8539(3) 0.7665(2) 0.0320(6) Uani 1 d . . .
H8A H 0.2505 0.9581 0.7530 0.041(7) Uiso 1 calc R . .
O9 O 0.3996(2) 0.8186(2) 0.75255(17) 0.0346(5) Uani 1 d . . .
C10 C 0.2630(3) 0.8274(3) 0.8885(2) 0.0312(6) Uani 1 d . . .
H10A H 0.1735 0.7777 0.8872 0.037(8) Uiso 1 calc R . .
C11 C 0.3876(3) 0.7372(3) 0.9521(2) 0.0310(6) Uani 1 d . . .
H11A H 0.4739 0.7981 0.9745 0.050(7) Uiso 1 calc R . .
O12 O 0.35849(19) 0.6901(2) 1.05156(16) 0.0353(5) Uani 1 d . . .
C13 C 0.4779(3) 0.6660(4) 1.1479(2) 0.0400(7) Uani 1 d . . .
H13A H 0.5583 0.7251 1.1432 0.044(9) Uiso 1 calc R . .
H13B H 0.5066 0.5652 1.1509 0.061(12) Uiso 1 calc R . .
C14 C 0.4378(3) 0.7037(3) 1.2521(2) 0.0345(6) Uani 1 d . . .
C15 C 0.3803(3) 0.8347(4) 1.2599(2) 0.0379(7) Uani 1 d . . .
H15A H 0.3604 0.8977 1.1973 0.045(9) Uiso 1 calc R . .
C16 C 0.3509(3) 0.8759(4) 1.3583(3) 0.0445(7) Uani 1 d . . .
H16A H 0.3114 0.9666 1.3627 0.050(10) Uiso 1 calc R . .
C17 C 0.3797(3) 0.7843(4) 1.4499(3) 0.0470(8) Uani 1 d . . .
H17A H 0.3628 0.8131 1.5181 0.082(14) Uiso 1 calc R . .
C18 C 0.4326(3) 0.6517(4) 1.4414(3) 0.0447(7) Uani 1 d . . .
H18A H 0.4490 0.5873 1.5029 0.055(10) Uiso 1 calc R . .
C19 C 0.4625(3) 0.6108(4) 1.3425(2) 0.0389(7) Uani 1 d . . .
H19A H 0.4998 0.5192 1.3373 0.048(10) Uiso 1 calc R . .
O20 O 0.27363(19) 0.9561(2) 0.95118(17) 0.0356(5) Uani 1 d . . .
C21 C 0.1415(3) 1.0247(5) 0.9366(3) 0.0570(10) Uani 1 d . . .
H21A H 0.0705 0.9549 0.9443 0.095(17) Uiso 1 calc R . .
H21B H 0.1077 1.0671 0.8602 0.081(15) Uiso 1 calc R . .
C22 C 0.1601(3) 1.1378(3) 1.0243(3) 0.0380(7) Uani 1 d . . .
C23 C 0.2034(3) 1.2723(4) 1.0072(3) 0.0456(8) Uani 1 d . . .
H23A H 0.2196 1.2945 0.9374 0.090(16) Uiso 1 calc R . .
C24 C 0.2236(4) 1.3745(4) 1.0887(4) 0.0568(10) Uani 1 d . . .
H24A H 0.2525 1.4671 1.0750 0.073(13) Uiso 1 calc R . .
C25 C 0.2017(3) 1.3424(4) 1.1915(3) 0.0567(10) Uani 1 d . . .
H25A H 0.2175 1.4122 1.2492 0.068(12) Uiso 1 calc R . .
C26 C 0.1572(4) 1.2099(5) 1.2089(3) 0.0533(9) Uani 1 d . . .
H26A H 0.1411 1.1879 1.2788 0.080(14) Uiso 1 calc R . .
C27 C 0.1356(3) 1.1082(4) 1.1265(3) 0.0459(8) Uani 1 d . . .
H27A H 0.1035 1.0167 1.1394 0.047(9) Uiso 1 calc R . .
C28 C 0.1732(3) 0.3999(3) 0.6700(2) 0.0332(6) Uani 1 d . . .
C29 C 0.2351(3) 0.3260(4) 0.6010(3) 0.0409(7) Uani 1 d . . .
H29A H 0.3166 0.3627 0.5857 0.066(12) Uiso 1 calc R . .
C30 C 0.1774(4) 0.1975(4) 0.5540(3) 0.0507(9) Uani 1 d . . .
H30A H 0.2202 0.1467 0.5068 0.060(11) Uiso 1 calc R . .
C31 C 0.0589(4) 0.1429(4) 0.5750(3) 0.0475(8) Uani 1 d . . .
H31A H 0.0202 0.0552 0.5425 0.067(12) Uiso 1 calc R . .
C32 C -0.0030(4) 0.2168(4) 0.6438(3) 0.0476(8) Uani 1 d . . .
H32A H -0.0846 0.1799 0.6588 0.062(11) Uiso 1 calc R . .
C33 C 0.0539(3) 0.3448(4) 0.6910(3) 0.0427(7) Uani 1 d . . .
H33A H 0.0107 0.3953 0.7381 0.058(11) Uiso 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'
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
O2 C1 O6 112.2(2) . . ?
O2 C1 O5 105.8(2) . . ?
O6 C1 O5 109.7(2) . . ?
O2 C1 C28 112.4(2) . . ?
O6 C1 C28 107.4(2) . . ?
O5 C1 C28 109.4(2) . . ?
C1 O2 C3 108.1(2) . . ?
O9 C3 O2 111.5(2) . . ?
O9 C3 C4 112.8(2) . . ?
O2 C3 C4 104.0(2) . . ?
O5 C4 C11 112.2(2) . . ?
O5 C4 C3 104.3(2) . . ?
C11 C4 C3 110.3(2) . . ?
C1 O5 C4 108.6(2) . . ?
C1 O6 C7 118.7(2) . . ?
O6 C7 C8 116.0(2) . . ?
O9 C8 C7 111.5(2) . . ?
O9 C8 C10 111.0(2) . . ?
C7 C8 C10 113.9(2) . . ?
C3 O9 C8 113.2(2) . . ?
O20 C10 C11 106.2(2) . . ?
O20 C10 C8 112.1(2) . . ?
C11 C10 C8 111.2(2) . . ?
O12 C11 C10 106.4(2) . . ?
O12 C11 C4 113.2(2) . . ?
C10 C11 C4 111.2(2) . . ?
C11 O12 C13 116.3(2) . . ?
O12 C13 C14 108.3(2) . . ?
C15 C14 C19 119.2(3) . . ?
C15 C14 C13 119.7(3) . . ?
C19 C14 C13 121.1(3) . . ?
C14 C15 C16 120.8(3) . . ?
C15 C16 C17 119.9(3) . . ?
C18 C17 C16 119.6(3) . . ?
C17 C18 C19 120.3(3) . . ?
C14 C19 C18 120.1(3) . . ?
C10 O20 C21 113.7(2) . . ?
O20 C21 C22 108.9(2) . . ?
C23 C22 C27 118.3(3) . . ?
C23 C22 C21 121.4(3) . . ?
C27 C22 C21 120.2(3) . . ?
C24 C23 C22 121.3(3) . . ?
C23 C24 C25 119.7(3) . . ?
C26 C25 C24 119.5(3) . . ?
C25 C26 C27 120.6(3) . . ?
C26 C27 C22 120.5(3) . . ?
C33 C28 C29 119.3(3) . . ?
C33 C28 C1 119.2(3) . . ?
C29 C28 C1 121.4(3) . . ?
C30 C29 C28 119.7(3) . . ?
C29 C30 C31 120.9(3) . . ?
C32 C31 C30 119.4(3) . . ?
C31 C32 C33 120.0(3) . . ?
C28 C33 C32 120.6(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
C1 O2 1.403(3) . ?
C1 O6 1.403(3) . ?
C1 O5 1.425(3) . ?
C1 C28 1.509(4) . ?
O2 C3 1.425(3) . ?
C3 O9 1.404(4) . ?
C3 C4 1.538(4) . ?
C4 O5 1.441(3) . ?
C4 C11 1.531(4) . ?
O6 C7 1.435(4) . ?
C7 C8 1.521(4) . ?
C8 O9 1.450(3) . ?
C8 C10 1.536(4) . ?
C10 O20 1.429(3) . ?
C10 C11 1.514(4) . ?
C11 O12 1.419(3) . ?
O12 C13 1.427(3) . ?
C13 C14 1.505(4) . ?
C14 C15 1.376(4) . ?
C14 C19 1.386(4) . ?
C15 C16 1.393(4) . ?
C16 C17 1.389(5) . ?
C17 C18 1.374(5) . ?
C18 C19 1.400(4) . ?
O20 C21 1.425(4) . ?
C21 C22 1.496(5) . ?
C22 C23 1.377(5) . ?
C22 C27 1.389(5) . ?
C23 C24 1.368(6) . ?
C24 C25 1.391(6) . ?
C25 C26 1.365(6) . ?
C26 C27 1.371(5) . ?
C28 C33 1.388(4) . ?
C28 C29 1.383(4) . ?
C29 C30 1.392(5) . ?
C30 C31 1.379(5) . ?
C31 C32 1.380(5) . ?
C32 C33 1.386(5) . ?
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
O6 C1 O2 C3 87.7(3) . . . . ?
O5 C1 O2 C3 -31.9(3) . . . . ?
C28 C1 O2 C3 -151.2(2) . . . . ?
C1 O2 C3 O9 -95.4(3) . . . . ?
C1 O2 C3 C4 26.4(3) . . . . ?
O9 C3 C4 O5 109.9(2) . . . . ?
O2 C3 C4 O5 -11.0(3) . . . . ?
O9 C3 C4 C11 -10.8(3) . . . . ?
O2 C3 C4 C11 -131.7(2) . . . . ?
O2 C1 O5 C4 24.1(3) . . . . ?
O6 C1 O5 C4 -97.1(2) . . . . ?
C28 C1 O5 C4 145.3(2) . . . . ?
C11 C4 O5 C1 111.7(2) . . . . ?
C3 C4 O5 C1 -7.7(3) . . . . ?
O2 C1 O6 C7 -20.8(3) . . . . ?
O5 C1 O6 C7 96.5(3) . . . . ?
C28 C1 O6 C7 -144.7(2) . . . . ?
C1 O6 C7 C8 -53.2(3) . . . . ?
O6 C7 C8 O9 80.5(3) . . . . ?
O6 C7 C8 C10 -46.2(3) . . . . ?
O2 C3 O9 C8 67.1(3) . . . . ?
C4 C3 O9 C8 -49.4(3) . . . . ?
C7 C8 O9 C3 -63.9(3) . . . . ?
C10 C8 O9 C3 64.4(3) . . . . ?
O9 C8 C10 O20 103.7(3) . . . . ?
C7 C8 C10 O20 -129.3(3) . . . . ?
O9 C8 C10 C11 -14.9(3) . . . . ?
C7 C8 C10 C11 112.0(3) . . . . ?
O20 C10 C11 O12 72.0(3) . . . . ?
C8 C10 C11 O12 -165.8(2) . . . . ?
O20 C10 C11 C4 -164.3(2) . . . . ?
C8 C10 C11 C4 -42.1(3) . . . . ?
O5 C4 C11 O12 60.3(3) . . . . ?
C3 C4 C11 O12 176.2(2) . . . . ?
O5 C4 C11 C10 -59.4(3) . . . . ?
C3 C4 C11 C10 56.5(3) . . . . ?
C10 C11 O12 C13 -150.1(2) . . . . ?
C4 C11 O12 C13 87.5(3) . . . . ?
C11 O12 C13 C14 146.3(3) . . . . ?
O12 C13 C14 C15 -52.9(4) . . . . ?
O12 C13 C14 C19 129.5(3) . . . . ?
C19 C14 C15 C16 1.9(4) . . . . ?
C13 C14 C15 C16 -175.7(3) . . . . ?
C14 C15 C16 C17 0.0(5) . . . . ?
C15 C16 C17 C18 -2.1(5) . . . . ?
C16 C17 C18 C19 2.4(5) . . . . ?
C15 C14 C19 C18 -1.6(4) . . . . ?
C13 C14 C19 C18 175.9(3) . . . . ?
C17 C18 C19 C14 -0.5(4) . . . . ?
C11 C10 O20 C21 -153.5(3) . . . . ?
C8 C10 O20 C21 84.9(3) . . . . ?
C10 O20 C21 C22 167.4(3) . . . . ?
O20 C21 C22 C23 86.6(4) . . . . ?
O20 C21 C22 C27 -92.6(4) . . . . ?
C27 C22 C23 C24 0.7(5) . . . . ?
C21 C22 C23 C24 -178.4(3) . . . . ?
C22 C23 C24 C25 0.7(5) . . . . ?
C23 C24 C25 C26 -1.4(5) . . . . ?
C24 C25 C26 C27 0.7(5) . . . . ?
C25 C26 C27 C22 0.8(5) . . . . ?
C23 C22 C27 C26 -1.5(4) . . . . ?
C21 C22 C27 C26 177.7(3) . . . . ?
O2 C1 C28 C33 -173.0(3) . . . . ?
O6 C1 C28 C33 -49.1(3) . . . . ?
O5 C1 C28 C33 69.9(3) . . . . ?
O2 C1 C28 C29 6.1(4) . . . . ?
O6 C1 C28 C29 129.9(3) . . . . ?
O5 C1 C28 C29 -111.1(3) . . . . ?
C33 C28 C29 C30 -0.3(4) . . . . ?
C1 C28 C29 C30 -179.3(3) . . . . ?
C28 C29 C30 C31 0.2(5) . . . . ?
C29 C30 C31 C32 -0.1(5) . . . . ?
C30 C31 C32 C33 0.1(5) . . . . ?
C29 C28 C33 C32 0.2(4) . . . . ?
C1 C28 C33 C32 179.3(3) . . . . ?
C31 C32 C33 C28 -0.1(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653047
