#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/18/4021836.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_4021836
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            'C17 H23 N O4'
_chemical_formula_weight         305.36
_chemical_name_systematic
; 

 ? 

;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.190(10)
_cell_angle_beta                 91.880(10)
_cell_angle_gamma                108.790(10)
_cell_formula_units_Z            1
_cell_length_a                   5.502(7)
_cell_length_b                   6.094(7)
_cell_length_c                   12.278(14)
_cell_measurement_temperature    293(2)
_cell_volume                     387.3(8)
_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 0.896
_diffrn_measured_fraction_theta_max 0.896
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2424
_diffrn_reflns_theta_full        25.75
_diffrn_reflns_theta_max         25.75
_diffrn_reflns_theta_min         3.55
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelopiped
_exptl_crystal_F_000             164
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.239
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2424
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.238
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0368
_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)+(0.0492P)²+0.0396P] where P=(Fo²+2Fc²)/3 

;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0893
_reflns_number_gt                2374
_reflns_number_total             2424
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0606554si20060515_023810_1.cif
_cod_original_formula_sum        'C17 H23 N O4         '
_cod_database_code               4021836
loop_
_symmetry_equiv_pos_as_xyz
'x, y, 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
C11 C 0.4884(3) 0.6245(3) 0.89039(13) 0.0177(3) Uani 1 1 d .
O12 O 0.3692(2) 0.7851(2) 0.94184(10) 0.0218(3) Uani 1 1 d .
C13 C 0.4869(4) 0.9059(3) 1.04688(15) 0.0277(4) Uani 1 1 d .
H13A H 0.3851 0.9980 1.0766 0.033 Uiso 1 1 calc R
H13B H 0.6572 1.0116 1.0369 0.033 Uiso 1 1 calc R
C14 C 0.5085(4) 0.7370(4) 1.12821(16) 0.0354(5) Uani 1 1 d .
H14A H 0.3379 0.6395 1.1434 0.042 Uiso 1 1 calc R
H14B H 0.5947 0.8238 1.1966 0.042 Uiso 1 1 calc R
C15 C 0.6600(4) 0.5843(4) 1.08118(16) 0.0331(5) Uani 1 1 d .
H15A H 0.6637 0.4707 1.1311 0.040 Uiso 1 1 calc R
H15B H 0.8358 0.6802 1.0728 0.040 Uiso 1 1 calc R
C16 C 0.5348(4) 0.4589(3) 0.96993(15) 0.0252(4) Uani 1 1 d .
H16A H 0.3715 0.3429 0.9809 0.030 Uiso 1 1 calc R
H16B H 0.6443 0.3780 0.9371 0.030 Uiso 1 1 calc R
C21 C 0.7200(3) 0.7539(3) 0.82649(12) 0.0168(3) Uani 1 1 d .
H21 H 0.7868 0.6374 0.7900 0.020 Uiso 1 1 calc R
O21 O 0.9310(2) 0.9304(2) 0.88730(10) 0.0236(3) Uani 1 1 d .
H21A H 1.0481 0.8778 0.8988 0.028 Uiso 1 1 calc R
C22 C 0.5986(3) 0.8557(3) 0.73751(13) 0.0163(3) Uani 1 1 d .
H22 H 0.5798 1.0048 0.7653 0.020 Uiso 1 1 calc R
C23 C 0.3310(3) 0.6649(3) 0.70661(13) 0.0204(4) Uani 1 1 d .
H23 H 0.1913 0.7319 0.7088 0.024 Uiso 1 1 calc R
C24 C 0.3034(3) 0.4869(3) 0.79153(14) 0.0199(3) Uani 1 1 d .
H24 H 0.3656 0.3623 0.7607 0.024 Uiso 1 1 calc R
C25 C 0.3618(4) 0.5708(3) 0.58965(15) 0.0310(4) Uani 1 1 d .
H25A H 0.2881 0.4022 0.5792 0.037 Uiso 1 1 calc R
H25B H 0.2783 0.6359 0.5364 0.037 Uiso 1 1 calc R
N26 N 0.7455(3) 0.8775(2) 0.63800(11) 0.0208(3) Uani 1 1 d .
C27 C 0.6940(4) 1.0520(3) 0.57211(14) 0.0243(4) Uani 1 1 d .
H27A H 0.7408 1.2006 0.6171 0.029 Uiso 1 1 calc R
H27B H 0.5110 1.0041 0.5522 0.029 Uiso 1 1 calc R
O241 O 0.0438(2) 0.3861(2) 0.81575(12) 0.0294(3) Uani 1 1 d .
H241 H 0.0254 0.2621 0.8410 0.035 Uiso 1 1 calc R
O251 O 0.6363(3) 0.6438(2) 0.57898(10) 0.0285(3) Uani 1 1 d .
C31 C 0.8390(3) 1.0850(3) 0.46813(13) 0.0220(4) Uani 1 1 d .
C32 C 0.8232(4) 1.2634(4) 0.40665(15) 0.0302(4) Uani 1 1 d .
H32 H 0.7169 1.3497 0.4271 0.036 Uiso 1 1 calc R
C33 C 0.9660(5) 1.3118(4) 0.31530(17) 0.0407(5) Uani 1 1 d .
H33 H 0.9561 1.4313 0.2752 0.049 Uiso 1 1 calc R
C34 C 1.1230(5) 1.1826(4) 0.28361(18) 0.0469(6) Uani 1 1 d .
H34 H 1.2193 1.2160 0.2227 0.056 Uiso 1 1 calc R
C35 C 1.1359(5) 1.0027(4) 0.3434(2) 0.0452(6) Uani 1 1 d .
H35 H 1.2405 0.9153 0.3222 0.054 Uiso 1 1 calc R
C36 C 0.9929(4) 0.9533(4) 0.43460(16) 0.0324(4) Uani 1 1 d .
H36 H 1.0003 0.8313 0.4735 0.039 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
O12 C11 C16 112.19(15)
O12 C11 C21 111.18(15)
C16 C11 C21 116.56(15)
O12 C11 C24 106.13(15)
C16 C11 C24 111.05(15)
C21 C11 C24 98.44(14)
C13 O12 C11 115.95(14)
O12 C13 C14 111.84(17)
C13 C14 C15 110.03(17)
C14 C15 C16 109.92(17)
C15 C16 C11 113.14(16)
O21 C21 C22 111.33(15)
O21 C21 C11 117.61(15)
C22 C21 C11 103.65(15)
N26 C22 C21 111.35(15)
N26 C22 C23 107.30(14)
C21 C22 C23 103.61(15)
C25 C23 C24 114.13(17)
C25 C23 C22 102.43(15)
C24 C23 C22 105.32(14)
O241 C24 C23 111.48(14)
O241 C24 C11 115.09(15)
C23 C24 C11 104.73(15)
O251 C25 C23 104.82(14)
O251 N26 C22 102.07(13)
O251 N26 C27 109.89(15)
C22 N26 C27 110.65(14)
N26 C27 C31 113.86(16)
C25 O251 N26 107.08(13)
C36 C31 C32 119.14(18)
C36 C31 C27 122.99(16)
C32 C31 C27 117.81(17)
C33 C32 C31 120.2(2)
C34 C33 C32 120.3(2)
C33 C34 C35 119.6(2)
C36 C35 C34 120.2(2)
C31 C36 C35 120.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C11 O12 1.454(2)
C11 C16 1.538(2)
C11 C21 1.546(2)
C11 C24 1.548(3)
O12 C13 1.446(3)
C13 C14 1.526(3)
C14 C15 1.525(3)
C15 C16 1.528(3)
C21 O21 1.434(2)
C21 C22 1.538(2)
C22 N26 1.479(2)
C22 C23 1.563(3)
C23 C25 1.533(3)
C23 C24 1.548(3)
C24 O241 1.414(3)
C25 O251 1.444(3)
N26 O251 1.465(2)
N26 C27 1.483(2)
C27 C31 1.522(3)
C31 C36 1.390(3)
C31 C32 1.401(3)
C32 C33 1.389(3)
C33 C34 1.387(4)
C34 C35 1.392(4)
C35 C36 1.389(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21194324
