#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/52/1505277.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_1505277
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            'C12 H17 N O5'
_chemical_formula_weight         255.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0623(12)
_cell_length_b                   10.3743(16)
_cell_length_c                   15.809(2)
_cell_measurement_reflns_used    704
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.19
_cell_measurement_theta_min      2.35
_cell_volume                     1322.3(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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8990
_diffrn_reflns_theta_full        28.03
_diffrn_reflns_theta_max         28.03
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.666879
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(13)
_refine_ls_extinction_coef       0.016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3198
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0419
_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)+(0.0608P)²+0.0752P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1241
_reflns_number_gt                1899
_reflns_number_total             3198
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol062873psi20061127_025947.cif
_cod_data_source_block           skca34
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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)2(1)2(1)
_cod_database_code               1505277
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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 0.9420(2) 0.10954(18) 0.77098(15) 0.0722(6) Uani 1 1 d .
O1 O 0.6251(3) 0.2959(3) 0.50177(12) 0.1204(10) Uani 1 1 d .
O2 O 0.50814(18) 0.37015(15) 0.61909(9) 0.0592(4) Uani 1 1 d .
O3 O 1.0909(2) 0.15786(17) 0.73559(15) 0.0918(7) Uani 1 1 d .
O4 O 0.6493(2) 0.24260(18) 0.88754(10) 0.0679(5) Uani 1 1 d .
O5 O 0.49925(19) 0.36595(15) 0.79864(9) 0.0607(4) Uani 1 1 d .
C1 C 0.3999(4) 0.4441(3) 0.49088(16) 0.0844(9) Uani 1 1 d .
H1B H 0.4143 0.4358 0.4308 0.127 Uiso 1 1 calc R
H1C H 0.4161 0.5324 0.5071 0.127 Uiso 1 1 calc R
H1D H 0.2899 0.4175 0.5061 0.127 Uiso 1 1 calc R
C2 C 0.5227(3) 0.3618(3) 0.53506(16) 0.0674(7) Uani 1 1 d .
C3 C 0.6296(2) 0.3019(2) 0.66960(13) 0.0475(5) Uani 1 1 d .
H3A H 0.6673 0.2260 0.6381 0.057 Uiso 1 1 calc R
C4 C 0.7766(3) 0.3893(2) 0.68512(16) 0.0573(6) Uani 1 1 d .
H4A H 0.7378 0.4709 0.7076 0.069 Uiso 1 1 calc R
H4B H 0.8322 0.4063 0.6319 0.069 Uiso 1 1 calc R
C5 C 0.9003(2) 0.32897(19) 0.74734(14) 0.0477(5) Uani 1 1 d .
H5A H 0.9175 0.3869 0.7955 0.057 Uiso 1 1 calc R
C6 C 1.0666(3) 0.2889(2) 0.71065(18) 0.0685(7) Uani 1 1 d .
H6A H 1.0654 0.2962 0.6495 0.082 Uiso 1 1 calc R
H6B H 1.1547 0.3430 0.7327 0.082 Uiso 1 1 calc R
C7 C 0.8403(2) 0.20124(19) 0.77789(14) 0.0478(5) Uani 1 1 d .
C8 C 0.6663(3) 0.1831(2) 0.80731(13) 0.0498(5) Uani 1 1 d .
H8A H 0.6372 0.0915 0.8099 0.060 Uiso 1 1 calc R
C9 C 0.5459(2) 0.25775(19) 0.74939(13) 0.0478(5) Uani 1 1 d .
H9A H 0.4487 0.2048 0.7360 0.057 Uiso 1 1 calc R
C10 C 0.5119(3) 0.3301(3) 0.88518(14) 0.0630(6) Uani 1 1 d .
C11 C 0.5571(4) 0.4487(3) 0.93491(17) 0.0926(10) Uani 1 1 d .
H11A H 0.6580 0.4846 0.9130 0.139 Uiso 1 1 calc R
H11B H 0.5724 0.4261 0.9933 0.139 Uiso 1 1 calc R
H11C H 0.4696 0.5111 0.9302 0.139 Uiso 1 1 calc R
C12 C 0.3565(3) 0.2635(4) 0.91516(19) 0.0958(10) Uani 1 1 d .
H12A H 0.3371 0.1882 0.8813 0.144 Uiso 1 1 calc R
H12B H 0.2640 0.3212 0.9100 0.144 Uiso 1 1 calc R
H12C H 0.3695 0.2387 0.9733 0.144 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
C7 N1 O3 108.56(17)
C2 O2 C3 117.18(19)
N1 O3 C6 109.22(16)
C8 O4 C10 109.12(16)
C9 O5 C10 107.61(16)
O1 C2 O2 122.4(2)
O1 C2 C1 125.7(3)
O2 C2 C1 111.9(3)
O2 C3 C9 107.94(16)
O2 C3 C4 109.05(17)
C9 C3 C4 113.51(17)
C3 C4 C5 111.65(17)
C7 C5 C6 99.60(16)
C7 C5 C4 111.06(17)
C6 C5 C4 116.13(19)
O3 C6 C5 106.03(19)
N1 C7 C8 122.95(19)
N1 C7 C5 115.59(19)
C8 C7 C5 121.26(17)
O4 C8 C7 108.38(18)
O4 C8 C9 104.57(15)
C7 C8 C9 110.10(17)
O5 C9 C3 109.82(16)
O5 C9 C8 103.80(16)
C3 C9 C8 111.63(16)
O5 C10 O4 104.26(17)
O5 C10 C11 107.8(2)
O4 C10 C11 108.5(2)
O5 C10 C12 111.3(2)
O4 C10 C12 110.1(2)
C11 C10 C12 114.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C7 1.260(3)
N1 O3 1.417(3)
O1 C2 1.194(3)
O2 C2 1.337(3)
O2 C3 1.449(2)
O3 C6 1.429(3)
O4 C8 1.417(3)
O4 C10 1.433(3)
O5 C9 1.417(2)
O5 C10 1.422(3)
C1 C2 1.482(4)
C3 C9 1.502(3)
C3 C4 1.512(3)
C4 C5 1.534(3)
C5 C7 1.491(3)
C5 C6 1.519(3)
C7 C8 1.490(3)
C8 C9 1.543(3)
C10 C11 1.505(4)
C10 C12 1.507(4)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21199615 ChemSpider
