#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/52/1505279.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_1505279
loop_
_publ_author_name
'Shing, Tony K. M.'
'Wong, Wai F.'
'Cheng, Hau M.'
'Kwok, Wun S.'
'So, King H.'
_publ_section_title
;
 Intramolecular nitrile oxide-alkene cycloaddition of sugar derivatives
 with unmasked hydroxyl group(s).
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              753
_journal_page_last               756
_journal_paper_doi               10.1021/ol062873p
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C13 H21 N O6'
_chemical_formula_weight         287.31
_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                 96.269(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.1732(19)
_cell_length_b                   7.1417(19)
_cell_length_c                   14.467(4)
_cell_measurement_reflns_used    714
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.85
_cell_measurement_theta_min      3.18
_cell_volume                     736.7(3)
_computing_cell_refinement       'BRUKER SMART CCD DIFFRACTOMETER'
_computing_data_collection       'BRUKER SMART CCD DIFFRACTOMETER'
_computing_data_reduction        'BRUKER SMART CCD DIFFRACTOMETER'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'BRUKER SMART CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA SCAN'
_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  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5042
_diffrn_reflns_theta_full        28.05
_diffrn_reflns_theta_max         28.05
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.745269
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3353
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0378
_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)+(0.0495P)²+0.1050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.1045
_reflns_number_gt                2641
_reflns_number_total             3353
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol062873psi20061127_030048.cif
_cod_data_source_block           wwf87
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1505279
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
N1 N 0.3910(2) 0.6293(2) 0.47018(11) 0.0409(4) Uani 1 1 d .
O1 O 0.43097(19) 0.6330(2) 0.56897(9) 0.0507(4) Uani 1 1 d .
O2 O 1.04535(18) 0.4628(2) 0.34942(10) 0.0545(4) Uani 1 1 d .
H2A H 1.1328 0.5220 0.3318 0.082 Uiso 1 1 calc R
O3 O 0.74965(17) 0.5651(2) 0.21783(9) 0.0426(3) Uani 1 1 d .
O4 O 0.39629(16) 0.5883(2) 0.28109(8) 0.0395(3) Uani 1 1 d .
O5 O 0.5647(2) 0.3068(2) 0.17205(12) 0.0575(4) Uani 1 1 d .
O6 O 0.4196(2) 0.7805(2) 0.15349(10) 0.0536(4) Uani 1 1 d .
C1 C 0.6333(3) 0.6374(3) 0.59196(13) 0.0455(5) Uani 1 1 d .
H1B H 0.6790 0.5165 0.6151 0.055 Uiso 1 1 calc R
H1C H 0.6682 0.7312 0.6392 0.055 Uiso 1 1 calc R
C2 C 0.7148(2) 0.6859(3) 0.50200(13) 0.0377(4) Uani 1 1 d .
H2B H 0.7507 0.8183 0.5026 0.045 Uiso 1 1 calc R
C3 C 0.5426(2) 0.6568(3) 0.43455(12) 0.0337(4) Uani 1 1 d .
C4 C 0.8773(2) 0.5661(3) 0.47607(13) 0.0406(4) Uani 1 1 d .
H4A H 0.8522 0.4356 0.4887 0.049 Uiso 1 1 calc R
H4B H 0.9912 0.6019 0.5144 0.049 Uiso 1 1 calc R
C5 C 0.9070(2) 0.5880(3) 0.37356(13) 0.0391(4) Uani 1 1 d .
H5A H 0.9438 0.7170 0.3613 0.047 Uiso 1 1 calc R
C6 C 0.7271(2) 0.5397(3) 0.31394(13) 0.0348(4) Uani 1 1 d .
H6A H 0.6972 0.4079 0.3242 0.042 Uiso 1 1 calc R
C7 C 0.5612(2) 0.6587(3) 0.33391(12) 0.0352(4) Uani 1 1 d .
H7A H 0.5824 0.7878 0.3146 0.042 Uiso 1 1 calc R
C8 C 0.5926(3) 0.5001(3) 0.15824(14) 0.0447(5) Uani 1 1 d .
C9 C 0.4070(3) 0.5932(3) 0.18296(12) 0.0416(4) Uani 1 1 d .
C10 C 0.6369(3) 0.5452(5) 0.06063(15) 0.0684(8) Uani 1 1 d .
H10A H 0.7519 0.4849 0.0494 0.103 Uiso 1 1 calc R
H10B H 0.6499 0.6782 0.0542 0.103 Uiso 1 1 calc R
H10C H 0.5370 0.5011 0.0164 0.103 Uiso 1 1 calc R
C11 C 0.7241(4) 0.1892(5) 0.1647(2) 0.0832(9) Uani 1 1 d .
H11A H 0.6912 0.0614 0.1757 0.125 Uiso 1 1 calc R
H11B H 0.8248 0.2268 0.2101 0.125 Uiso 1 1 calc R
H11C H 0.7630 0.2006 0.1036 0.125 Uiso 1 1 calc R
C12 C 0.2322(3) 0.4944(4) 0.13914(16) 0.0579(6) Uani 1 1 d .
H12A H 0.1230 0.5573 0.1565 0.087 Uiso 1 1 calc R
H12B H 0.2326 0.3671 0.1605 0.087 Uiso 1 1 calc R
H12C H 0.2303 0.4962 0.0727 0.087 Uiso 1 1 calc R
C13 C 0.2651(4) 0.8976(4) 0.16801(18) 0.0705(7) Uani 1 1 d .
H13A H 0.2872 1.0215 0.1459 0.106 Uiso 1 1 calc R
H13B H 0.2510 0.9024 0.2332 0.106 Uiso 1 1 calc R
H13C H 0.1528 0.8479 0.1347 0.106 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'
N N 0.0061 0.0033 '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
C3 N1 O1 108.46(15)
N1 O1 C1 108.43(12)
C8 O3 C6 112.52(14)
C7 O4 C9 113.04(13)
C8 O5 C11 115.9(2)
C9 O6 C13 115.86(19)
O1 C1 C2 106.02(15)
C3 C2 C1 99.13(14)
C3 C2 C4 111.02(15)
C1 C2 C4 117.21(16)
N1 C3 C7 125.15(16)
N1 C3 C2 115.97(16)
C7 C3 C2 118.87(14)
C2 C4 C5 111.84(15)
O2 C5 C6 107.13(16)
O2 C5 C4 110.62(16)
C6 C5 C4 109.24(14)
O3 C6 C5 110.26(13)
O3 C6 C7 106.79(14)
C5 C6 C7 113.73(15)
O4 C7 C3 111.45(13)
O4 C7 C6 108.82(15)
C3 C7 C6 109.87(14)
O5 C8 O3 110.41(18)
O5 C8 C10 112.8(2)
O3 C8 C10 105.24(17)
O5 C8 C9 104.26(17)
O3 C8 C9 111.15(16)
C10 C8 C9 113.14(18)
O6 C9 O4 109.62(16)
O6 C9 C12 113.13(18)
O4 C9 C12 105.79(16)
O6 C9 C8 104.47(16)
O4 C9 C8 110.84(14)
C12 C9 C8 113.08(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C3 1.269(2)
N1 O1 1.427(2)
O1 C1 1.454(2)
O2 C5 1.408(2)
O3 C8 1.420(2)
O3 C6 1.429(2)
O4 C7 1.428(2)
O4 C9 1.430(2)
O5 C8 1.412(3)
O5 C11 1.431(3)
O6 C9 1.409(3)
O6 C13 1.422(3)
C1 C2 1.524(3)
C2 C3 1.503(2)
C2 C4 1.526(3)
C3 C7 1.477(2)
C4 C5 1.529(3)
C5 C6 1.511(2)
C6 C7 1.516(2)
C8 C10 1.516(3)
C8 C9 1.564(3)
C9 C12 1.516(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21199613
