#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/18/4021839.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_4021839
loop_
_publ_author_name
'Sk. Sahabuddin'
'Ashim Roy'
'Michael G. B. Drew'
'Biswajit Gopal Roy'
'Basudeb Achari'
'Sukhendu B. Mandal'
_publ_section_title
;
 Sequential Ring-Closing Metathesis and Nitrone Cycloaddition on
 Glucose-Derived Substrates: A Divergent Approach to Analogues of
 Spiroannulated Carbanucleosides and Conformationally Locked Nucleosides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5980
_journal_page_last               5992
_journal_paper_doi               10.1021/jo0606554
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C14 H17 N O4'
_chemical_formula_weight         263.28
_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                   6.240(9)
_cell_length_b                   10.604(12)
_cell_length_c                   19.21(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1271(3)
_computing_cell_refinement       XDS
_computing_data_collection       'XDS (Kabsch, 1988)'
_computing_data_reduction        XDS
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.872
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_device       'Marresearch Image Plate'
_diffrn_measurement_method
'95 frames at 2 degree intervals, counting time 2 min.'
_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  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5729
_diffrn_reflns_theta_full        25.74
_diffrn_reflns_theta_max         25.74
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelopiped
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2.1(15)
_refine_ls_extinction_coef       0.040(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.936
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;

  w=1/[σ²(Fo²)+(0.0823P)²+0.1721P] where P=(Fo²+2Fc²)/3 

;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1195
_reflns_number_gt                1811
_reflns_number_total             2129
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0606554si20060515_023810_4.cif
_cod_database_code               4021839
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1/2, -y, z+1/2'
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 0.5025(3) 0.81554(19) 0.37114(14) 0.0361(6) Uani 1 1 d .
C2 C 0.2927(4) 0.75240(19) 0.36882(15) 0.0270(6) Uani 1 1 d .
H2 H 0.2369 0.7386 0.4159 0.032 Uiso 1 1 calc R
C3 C 0.2972(4) 0.62585(19) 0.32650(16) 0.0311(6) Uani 1 1 d .
H3 H 0.4455 0.6051 0.3142 0.037 Uiso 1 1 calc R
O3 O 0.2060(3) 0.52447(15) 0.36576(13) 0.0472(6) Uani 1 1 d .
H3A H 0.0818 0.5418 0.3759 0.057 Uiso 1 1 calc R
C4 C 0.1699(4) 0.6539(2) 0.26027(15) 0.0315(6) Uani 1 1 d .
H4 H 0.1040 0.5769 0.2419 0.038 Uiso 1 1 calc R
C5 C -0.0017(4) 0.7462(2) 0.28635(16) 0.0297(6) Uani 1 1 d .
H5 H -0.0812 0.7863 0.2483 0.036 Uiso 1 1 calc R
O5 O -0.1363(3) 0.67642(16) 0.33198(12) 0.0382(5) Uani 1 1 d .
H5A H -0.2291 0.7230 0.3479 0.046 Uiso 1 1 calc R
C6 C 0.1412(3) 0.83963(19) 0.32643(14) 0.0231(5) Uani 1 1 d .
H6 H 0.0598 0.8984 0.3556 0.028 Uiso 1 1 calc R
O7 O 0.5120(3) 0.88980(16) 0.30743(12) 0.0416(5) Uani 1 1 d .
C8 C 0.2996(4) 0.9054(2) 0.27749(16) 0.0331(7) Uani 1 1 d .
H8 H 0.2646 0.9953 0.2738 0.040 Uiso 1 1 calc R
C9 C 0.3012(6) 0.8459(2) 0.20597(18) 0.0480(8) Uani 1 1 d .
H9A H 0.1744 0.8724 0.1806 0.058 Uiso 1 1 calc R
H9B H 0.4258 0.8752 0.1805 0.058 Uiso 1 1 calc R
O10 O 0.3056(4) 0.71080(16) 0.20958(13) 0.0491(6) Uani 1 1 d .
C11 C 0.5321(5) 0.9026(3) 0.4313(2) 0.0517(9) Uani 1 1 d .
H11A H 0.6661 0.9473 0.4248 0.062 Uiso 1 1 calc R
H11B H 0.5468 0.8518 0.4731 0.062 Uiso 1 1 calc R
C12 C 0.3579(4) 0.9992(2) 0.44420(16) 0.0340(7) Uani 1 1 d .
C13 C 0.3494(5) 1.1081(2) 0.40405(17) 0.0392(7) Uani 1 1 d .
H13 H 0.4579 1.1244 0.3721 0.047 Uiso 1 1 calc R
C14 C 0.1818(6) 1.1925(3) 0.41092(17) 0.0471(8) Uani 1 1 d .
H14 H 0.1779 1.2644 0.3832 0.057 Uiso 1 1 calc R
C15 C 0.0221(6) 1.1711(3) 0.4580(2) 0.0532(9) Uani 1 1 d .
H15 H -0.0921 1.2271 0.4614 0.064 Uiso 1 1 calc R
C16 C 0.0300(5) 1.0676(3) 0.5001(2) 0.0561(10) Uani 1 1 d .
H16 H -0.0764 1.0546 0.5332 0.067 Uiso 1 1 calc R
C17 C 0.1982(6) 0.9810(3) 0.49344(17) 0.0463(8) Uani 1 1 d .
H17 H 0.2028 0.9106 0.5223 0.056 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
O7 N1 C2 104.9(2)
O7 N1 C11 108.2(2)
C2 N1 C11 114.6(2)
N1 C2 C6 106.6(2)
N1 C2 C3 112.9(2)
C6 C2 C3 104.4(2)
O3 C3 C4 112.2(2)
O3 C3 C2 111.2(3)
C4 C3 C2 104.79(19)
O10 C4 C3 110.0(2)
O10 C4 C5 111.6(2)
C3 C4 C5 102.4(2)
O5 C5 C4 106.4(2)
O5 C5 C6 111.6(2)
C4 C5 C6 99.8(2)
C8 C6 C5 111.1(2)
C8 C6 C2 101.5(2)
C5 C6 C2 103.37(18)
C8 O7 N1 110.89(18)
O7 C8 C9 107.8(2)
O7 C8 C6 107.1(2)
C9 C8 C6 111.8(2)
O10 C9 C8 111.9(2)
C4 O10 C9 116.4(2)
N1 C11 C12 117.2(2)
C17 C12 C13 117.8(3)
C17 C12 C11 122.2(3)
C13 C12 C11 119.9(3)
C14 C13 C12 120.9(3)
C15 C14 C13 120.5(3)
C16 C15 C14 120.0(3)
C15 C16 C17 120.1(3)
C12 C17 C16 120.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 O7 1.456(4)
N1 C2 1.471(4)
N1 C11 1.491(4)
C2 C6 1.553(4)
C2 C3 1.569(4)
C3 O3 1.431(3)
C3 C4 1.529(4)
C4 O10 1.424(4)
C4 C5 1.534(4)
C5 O5 1.421(4)
C5 C6 1.539(4)
C6 C8 1.532(4)
O7 C8 1.454(4)
C8 C9 1.512(5)
C9 O10 1.434(4)
C11 C12 1.514(4)
C12 C17 1.387(4)
C12 C13 1.389(4)
C13 C14 1.383(5)
C14 C15 1.365(5)
C15 C16 1.363(5)
C16 C17 1.400(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21194322
