#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/41/4024149.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_4024149
loop_
_publ_author_name
'Medha N. Kamat'
'Nigam P. Rath'
'Alexei V. Demchenko'
_publ_section_title
;
 Versatile Synthesis and Mechanism of Activation of S-Benzoxazolyl
 Glycosides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6938
_journal_page_last               6946
_journal_paper_doi               10.1021/jo0711844
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C26 H27 N O9 S'
_chemical_formula_weight         529.55
_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                 105.935(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.5994(16)
_cell_length_b                   6.3161(8)
_cell_length_c                   14.6613(17)
_cell_measurement_reflns_used    1495
_cell_measurement_temperature    165(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      2.3
_cell_volume                     1300.0(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker-SHELXTL (Sheldrick, 2002)'
_computing_publication_material  'Bruker-SHELXTL (Sheldrick, 2002)'
_computing_structure_refinement  'Bruker-SHELXTL (Sheldrick, 2002)'
_computing_structure_solution    'Bruker-SHELXTL (Sheldrick, 2002)'
_diffrn_ambient_temperature      165(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.1896
_diffrn_reflns_av_sigmaI/netI    0.4203
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15119
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.44
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_correction_T_min  0.9484
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4549
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.2833
_refine_ls_R_factor_gt           0.0843
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0195P)²+0.3801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1652
_reflns_number_gt                1574
_reflns_number_total             4549
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0711844-File005.cif
_cod_data_source_block           d7203
_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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'no' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4024149
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.65563(19) 0.8477(4) 0.2860(2) 0.0428(8) Uani 1 1 d . . .
O1 O 0.7779(4) 0.6286(9) 0.2197(4) 0.0346(18) Uani 1 1 d . . .
O2 O 0.9794(4) 0.4805(9) 0.1428(4) 0.0361(17) Uani 1 1 d . . .
O3 O 0.9443(6) 0.4478(12) -0.0147(5) 0.056(2) Uani 1 1 d . . .
O4 O 0.4900(5) 0.8014(10) 0.1622(5) 0.042(2) Uani 1 1 d . . .
O5 O 0.7395(4) 0.5225(10) 0.4527(4) 0.0351(17) Uani 1 1 d . . .
O6 O 0.8368(4) 0.1556(9) 0.4237(5) 0.0320(17) Uani 1 1 d . . .
O7 O 0.9634(5) 0.2322(11) 0.5468(5) 0.042(2) Uani 1 1 d . . .
O8 O 0.9561(4) 0.2114(9) 0.3010(4) 0.0323(18) Uani 1 1 d . . .
O9 O 0.9054(5) 0.0056(11) 0.1713(5) 0.049(2) Uani 1 1 d . . .
N1 N 0.5733(6) 0.4955(14) 0.1858(6) 0.034(2) Uani 1 1 d . . .
C1 C 0.7585(6) 0.6733(15) 0.3079(7) 0.038(3) Uani 1 1 d . . .
H1 H 0.8142 0.7550 0.3471 0.046 Uiso 1 1 calc R . .
C2 C 0.7524(7) 0.4687(15) 0.3621(7) 0.031(3) Uani 1 1 d . . .
H2 H 0.6985 0.3787 0.3254 0.037 Uiso 1 1 calc R . .
C3 C 0.8451(6) 0.3544(14) 0.3766(6) 0.029(2) Uani 1 1 d . . .
H3 H 0.8979 0.4411 0.4174 0.035 Uiso 1 1 calc R . .
C4 C 0.8637(6) 0.3142(15) 0.2821(6) 0.028(3) Uani 1 1 d . . .
H4 H 0.8130 0.2212 0.2420 0.033 Uiso 1 1 calc R . .
C5 C 0.8682(7) 0.5254(14) 0.2315(7) 0.036(3) Uani 1 1 d . . .
H5 H 0.9207 0.6155 0.2707 0.043 Uiso 1 1 calc R . .
C6 C 0.8785(6) 0.5026(16) 0.1329(6) 0.036(3) Uani 1 1 d . . .
H6A H 0.8436 0.3762 0.1015 0.043 Uiso 1 1 calc R . .
H6B H 0.8529 0.6290 0.0944 0.043 Uiso 1 1 calc R . .
C7 C 1.0051(9) 0.4573(15) 0.0614(9) 0.044(3) Uani 1 1 d . . .
C8 C 1.1088(7) 0.4481(17) 0.0766(7) 0.061(4) Uani 1 1 d . . .
H8A H 1.1339 0.3195 0.1121 0.091 Uiso 1 1 calc R . .
H8B H 1.1384 0.5726 0.1128 0.091 Uiso 1 1 calc R . .
H8C H 1.1232 0.4462 0.0152 0.091 Uiso 1 1 calc R . .
C9 C 0.5719(7) 0.6880(18) 0.2087(7) 0.036(3) Uani 1 1 d . . .
C10 C 0.4874(8) 0.4644(19) 0.1169(7) 0.038(3) Uani 1 1 d . . .
C11 C 0.4534(7) 0.2845(15) 0.0614(7) 0.033(3) Uani 1 1 d . . .
H11 H 0.4875 0.1547 0.0686 0.040 Uiso 1 1 calc R . .
C12 C 0.3667(7) 0.3123(18) -0.0043(8) 0.050(3) Uani 1 1 d . . .
H12 H 0.3398 0.1941 -0.0423 0.060 Uiso 1 1 calc R . .
C13 C 0.3159(7) 0.499(2) -0.0189(8) 0.053(3) Uani 1 1 d . . .
H13 H 0.2575 0.5071 -0.0673 0.063 Uiso 1 1 calc R . .
C14 C 0.3496(8) 0.672(2) 0.0365(8) 0.052(3) Uani 1 1 d . . .
H14 H 0.3142 0.7997 0.0299 0.062 Uiso 1 1 calc R . .
C15 C 0.4372(8) 0.6523(18) 0.1021(8) 0.042(3) Uani 1 1 d . . .
C16 C 0.6488(7) 0.4570(17) 0.4616(7) 0.052(3) Uani 1 1 d . . .
H16A H 0.6410 0.3023 0.4516 0.063 Uiso 1 1 calc R . .
H16B H 0.5973 0.5295 0.4136 0.063 Uiso 1 1 calc R . .
C17 C 0.6446(8) 0.513(2) 0.5588(9) 0.052(3) Uani 1 1 d . . .
C18 C 0.6104(8) 0.717(2) 0.5768(10) 0.078(4) Uani 1 1 d . . .
H18 H 0.5854 0.8116 0.5257 0.094 Uiso 1 1 calc R . .
C19 C 0.6138(10) 0.776(3) 0.6679(13) 0.095(6) Uani 1 1 d . . .
H19 H 0.5921 0.9121 0.6798 0.114 Uiso 1 1 calc R . .
C20 C 0.6486(13) 0.637(4) 0.7422(13) 0.123(8) Uani 1 1 d . . .
H20 H 0.6498 0.6795 0.8048 0.148 Uiso 1 1 calc R . .
C21 C 0.6815(11) 0.440(3) 0.7275(12) 0.115(7) Uani 1 1 d . . .
H21 H 0.7038 0.3435 0.7783 0.137 Uiso 1 1 calc R . .
C22 C 0.6808(8) 0.390(2) 0.6375(10) 0.077(5) Uani 1 1 d . . .
H22 H 0.7077 0.2576 0.6281 0.093 Uiso 1 1 calc R . .
C23 C 0.8942(8) 0.1251(16) 0.5113(8) 0.037(3) Uani 1 1 d . . .
C24 C 0.8650(7) -0.0662(15) 0.5569(7) 0.050(3) Uani 1 1 d . . .
H24A H 0.9003 -0.1900 0.5446 0.075 Uiso 1 1 calc R . .
H24B H 0.7966 -0.0904 0.5304 0.075 Uiso 1 1 calc R . .
H24C H 0.8791 -0.0434 0.6254 0.075 Uiso 1 1 calc R . .
C25 C 0.9666(8) 0.0624(14) 0.2373(8) 0.033(3) Uani 1 1 d . . .
C26 C 1.0679(7) -0.0132(17) 0.2607(6) 0.048(3) Uani 1 1 d . . .
H26A H 1.0758 -0.1075 0.2103 0.073 Uiso 1 1 calc R . .
H26B H 1.0835 -0.0902 0.3211 0.073 Uiso 1 1 calc R . .
H26C H 1.1106 0.1087 0.2661 0.073 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
C9 S1 C1 99.3(5) . . ?
C1 O1 C5 112.6(7) . . ?
C7 O2 C6 116.3(8) . . ?
C15 O4 C9 102.5(7) . . ?
C16 O5 C2 112.2(7) . . ?
C23 O6 C3 117.9(7) . . ?
C25 O8 C4 116.7(8) . . ?
C9 N1 C10 104.6(9) . . ?
O1 C1 C2 110.9(7) . . ?
O1 C1 S1 108.6(6) . . ?
C2 C1 S1 116.1(6) . . ?
O5 C2 C3 109.1(7) . . ?
O5 C2 C1 108.8(8) . . ?
C3 C2 C1 107.5(7) . . ?
O6 C3 C2 107.1(7) . . ?
O6 C3 C4 110.6(7) . . ?
C2 C3 C4 109.6(7) . . ?
O8 C4 C3 107.0(7) . . ?
O8 C4 C5 108.6(7) . . ?
C3 C4 C5 109.9(8) . . ?
O1 C5 C6 105.0(8) . . ?
O1 C5 C4 107.0(7) . . ?
C6 C5 C4 114.2(8) . . ?
O2 C6 C5 106.3(8) . . ?
O3 C7 O2 120.2(11) . . ?
O3 C7 C8 126.7(11) . . ?
O2 C7 C8 113.2(11) . . ?
N1 C9 O4 115.9(9) . . ?
N1 C9 S1 132.1(10) . . ?
O4 C9 S1 111.9(8) . . ?
C15 C10 N1 109.0(10) . . ?
C15 C10 C11 121.1(10) . . ?
N1 C10 C11 129.7(11) . . ?
C12 C11 C10 114.3(9) . . ?
C11 C12 C13 124.9(10) . . ?
C14 C13 C12 120.0(10) . . ?
C13 C14 C15 117.1(11) . . ?
O4 C15 C14 129.6(11) . . ?
O4 C15 C10 108.0(10) . . ?
C14 C15 C10 122.4(11) . . ?
O5 C16 C17 107.6(8) . . ?
C22 C17 C18 115.4(12) . . ?
C22 C17 C16 124.1(12) . . ?
C18 C17 C16 120.1(12) . . ?
C19 C18 C17 120.1(14) . . ?
C18 C19 C20 120.2(16) . . ?
C21 C20 C19 121.2(17) . . ?
C22 C21 C20 117.2(17) . . ?
C21 C22 C17 125.7(14) . . ?
O7 C23 O6 124.1(9) . . ?
O7 C23 C24 124.5(10) . . ?
O6 C23 C24 111.3(10) . . ?
O9 C25 O8 124.8(10) . . ?
O9 C25 C26 124.6(10) . . ?
O8 C25 C26 110.6(10) . . ?
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
S1 C9 1.742(10) . ?
S1 C1 1.819(9) . ?
O1 C1 1.427(10) . ?
O1 C5 1.438(9) . ?
O2 C7 1.354(11) . ?
O2 C6 1.447(9) . ?
O3 C7 1.222(11) . ?
O4 C15 1.373(11) . ?
O4 C9 1.400(11) . ?
O5 C16 1.426(9) . ?
O5 C2 1.433(10) . ?
O6 C23 1.341(11) . ?
O6 C3 1.454(9) . ?
O7 C23 1.209(11) . ?
O8 C25 1.363(10) . ?
O8 C4 1.454(9) . ?
O9 C25 1.178(10) . ?
N1 C9 1.263(12) . ?
N1 C10 1.393(11) . ?
C1 C2 1.532(11) . ?
C2 C3 1.496(10) . ?
C3 C4 1.505(11) . ?
C4 C5 1.537(12) . ?
C5 C6 1.501(11) . ?
C7 C8 1.469(12) . ?
C10 C15 1.380(13) . ?
C10 C11 1.407(13) . ?
C11 C12 1.375(13) . ?
C12 C13 1.375(14) . ?
C13 C14 1.371(13) . ?
C14 C15 1.379(13) . ?
C16 C17 1.487(13) . ?
C17 C22 1.373(15) . ?
C17 C18 1.428(15) . ?
C18 C19 1.375(16) . ?
C19 C20 1.38(2) . ?
C20 C21 1.37(2) . ?
C21 C22 1.355(18) . ?
C23 C24 1.498(12) . ?
C25 C26 1.502(12) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9960542
