#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/41/4024155.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_4024155
loop_
_publ_author_name
'Subhankar Tripathi'
'Biswajit G. Roy'
'Michael G. B. Drew'
'Basudeb Achari'
'Sukhendu B. Mandal'
_publ_section_title
;
 Synthesis of Oxepane Ring Containing Monocyclic, Conformationally
 Restricted Bicyclic and Spirocyclic Nucleosides from D-Glucose:
 A Cycloaddition Approach
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7427
_journal_page_last               7430
_journal_paper_doi               10.1021/jo070846m
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C26 H31 N O6'
_chemical_formula_weight         453.52
_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                   5.6097(5)
_cell_length_b                   18.1997(13)
_cell_length_c                   21.936(2)
_cell_measurement_temperature    150(2)
_cell_volume                     2239.5(3)
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'Oxford Diffaction X-Calibur System'
_diffrn_measurement_method       '321 frames, counting time 10 s.'
_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  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0773
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12851
_diffrn_reflns_theta_full        30.10
_diffrn_reflns_theta_max         30.10
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         6338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0616
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
  w=1/[σ²(Fo²)+(0.0439P)²+0.5899P] where P=(Fo²+2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1216
_reflns_number_gt                4638
_reflns_number_total             6338
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070846m-File003.cif
_cod_data_source_block           43
_cod_original_formula_sum        C26H31NO6
_cod_database_code               4024155
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C3 C -0.0277(4) 1.16510(14) 0.00747(12) 0.0260(5) Uani 1 1 d . . .
H3 H 0.0079 1.2091 -0.0166 0.031 Uiso 1 1 calc R . .
C4 C -0.1617(5) 1.11003(13) -0.03125(12) 0.0277(6) Uani 1 1 d . . .
H4A H -0.3298 1.1224 -0.0303 0.033 Uiso 1 1 calc R . .
H4B H -0.1080 1.1149 -0.0731 0.033 Uiso 1 1 calc R . .
C6 C -0.1977(4) 1.01981(13) 0.04795(10) 0.0206(5) Uani 1 1 d . . .
H6A H -0.2604 0.9702 0.0502 0.025 Uiso 1 1 calc R . .
H6B H -0.3232 1.0532 0.0606 0.025 Uiso 1 1 calc R . .
C7 C 0.0128(4) 1.02690(12) 0.09230(10) 0.0171(4) Uani 1 1 d . . .
C8 C 0.1168(4) 1.10435(12) 0.09556(11) 0.0186(5) Uani 1 1 d . . .
H8 H 0.2500 1.1051 0.1245 0.022 Uiso 1 1 calc R . .
C9 C 0.2004(4) 1.13366(13) 0.03379(11) 0.0220(5) Uani 1 1 d . . .
H9A H 0.3211 1.1714 0.0386 0.026 Uiso 1 1 calc R . .
H9B H 0.2630 1.0945 0.0084 0.026 Uiso 1 1 calc R . .
C10 C 0.0332(4) 1.21966(13) 0.14829(12) 0.0252(5) Uani 1 1 d . . .
H10A H 0.1250 1.2491 0.1199 0.030 Uiso 1 1 calc R . .
H10B H 0.1399 1.2027 0.1801 0.030 Uiso 1 1 calc R . .
C11 C 0.1933(4) 0.91073(12) 0.09996(10) 0.0199(5) Uani 1 1 d . . .
H11 H 0.3491 0.8940 0.1147 0.024 Uiso 1 1 calc R . .
C13 C -0.0833(4) 0.81750(12) 0.09057(11) 0.0198(5) Uani 1 1 d . . .
C15 C 0.0116(4) 0.91489(12) 0.15253(11) 0.0180(5) Uani 1 1 d . . .
H15 H 0.0807 0.8986 0.1913 0.022 Uiso 1 1 calc R . .
C16 C -0.0634(4) 0.99568(11) 0.15473(10) 0.0180(5) Uani 1 1 d . . .
H16 H -0.2363 0.9999 0.1601 0.022 Uiso 1 1 calc R . .
C17 C -0.0552(4) 1.02243(14) 0.25965(11) 0.0233(5) Uani 1 1 d . . .
H17A H -0.0837 0.9704 0.2661 0.028 Uiso 1 1 calc R . .
H17B H -0.2082 1.0473 0.2594 0.028 Uiso 1 1 calc R . .
C31 C -0.1608(4) 1.26621(12) 0.17614(11) 0.0219(5) Uani 1 1 d . . .
C32 C -0.1944(5) 1.33912(13) 0.16008(12) 0.0264(5) Uani 1 1 d . . .
H32 H -0.0975 1.3602 0.1305 0.032 Uiso 1 1 calc R . .
C33 C -0.3715(5) 1.38128(13) 0.18775(12) 0.0285(6) Uani 1 1 d . . .
H33 H -0.3926 1.4301 0.1766 0.034 Uiso 1 1 calc R . .
C34 C -0.5150(4) 1.35029(14) 0.23165(12) 0.0288(6) Uani 1 1 d . . .
H34 H -0.6321 1.3784 0.2506 0.035 Uiso 1 1 calc R . .
C35 C -0.4851(5) 1.27744(14) 0.24761(13) 0.0300(6) Uani 1 1 d . . .
H35 H -0.5828 1.2565 0.2771 0.036 Uiso 1 1 calc R . .
C36 C -0.3102(5) 1.23554(14) 0.21980(12) 0.0287(6) Uani 1 1 d . . .
H36 H -0.2924 1.1864 0.2304 0.034 Uiso 1 1 calc R . .
C131 C -0.2784(4) 0.79460(13) 0.04776(12) 0.0260(6) Uani 1 1 d . . .
H13D H -0.2157 0.7610 0.0181 0.039 Uiso 1 1 calc R . .
H13E H -0.3409 0.8371 0.0274 0.039 Uiso 1 1 calc R . .
H13F H -0.4035 0.7711 0.0704 0.039 Uiso 1 1 calc R . .
C132 C 0.0333(5) 0.75304(13) 0.12348(12) 0.0262(5) Uani 1 1 d . . .
H13A H 0.1069 0.7211 0.0942 0.039 Uiso 1 1 calc R . .
H13B H -0.0856 0.7263 0.1458 0.039 Uiso 1 1 calc R . .
H13C H 0.1520 0.7711 0.1512 0.039 Uiso 1 1 calc R . .
C171 C 0.0944(4) 1.05196(12) 0.31072(11) 0.0198(5) Uani 1 1 d . . .
C172 C 0.0284(4) 1.03731(13) 0.37081(11) 0.0239(5) Uani 1 1 d . . .
H172 H -0.1131 1.0124 0.3786 0.029 Uiso 1 1 calc R . .
C173 C 0.1705(5) 1.05930(14) 0.41906(11) 0.0287(6) Uani 1 1 d . . .
H173 H 0.1244 1.0494 0.4590 0.034 Uiso 1 1 calc R . .
C174 C 0.3830(5) 1.09630(14) 0.40750(12) 0.0285(6) Uani 1 1 d . . .
H174 H 0.4806 1.1105 0.4397 0.034 Uiso 1 1 calc R . .
C175 C 0.4483(4) 1.11189(13) 0.34865(12) 0.0253(5) Uani 1 1 d . . .
H175 H 0.5892 1.1373 0.3412 0.030 Uiso 1 1 calc R . .
C176 C 0.3053(4) 1.08999(12) 0.29987(11) 0.0220(5) Uani 1 1 d . . .
H176 H 0.3510 1.1008 0.2601 0.026 Uiso 1 1 calc R . .
O2 O -0.1743(3) 1.18450(9) 0.05979(8) 0.0294(4) Uani 1 1 d . . .
O5 O -0.1357(3) 1.03541(9) -0.01332(7) 0.0240(4) Uani 1 1 d . . .
O10 O 0.2100(3) 0.98058(8) 0.07357(7) 0.0196(4) Uani 1 1 d . . .
O12 O 0.0925(3) 0.85894(8) 0.05847(7) 0.0220(4) Uani 1 1 d . . .
O14 O -0.1805(3) 0.86885(8) 0.13367(7) 0.0210(4) Uani 1 1 d . . .
O16 O 0.0588(3) 1.03272(9) 0.20256(7) 0.0206(4) Uani 1 1 d . . .
N1 N -0.0691(3) 1.15575(10) 0.11602(9) 0.0211(4) Uani 1 1 d . . .
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'
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
O2 C3 C4 108.8(2) . . ?
O2 C3 C9 105.6(2) . . ?
C4 C3 C9 112.5(2) . . ?
O5 C4 C3 115.2(2) . . ?
O5 C6 C7 113.29(18) . . ?
O10 C7 C8 104.98(16) . . ?
O10 C7 C6 110.99(17) . . ?
C8 C7 C6 113.64(19) . . ?
O10 C7 C16 104.41(17) . . ?
C8 C7 C16 113.84(18) . . ?
C6 C7 C16 108.55(17) . . ?
N1 C8 C7 109.30(17) . . ?
N1 C8 C9 105.41(18) . . ?
C7 C8 C9 113.42(19) . . ?
C3 C9 C8 102.14(18) . . ?
N1 C10 C31 110.86(18) . . ?
O10 C11 O12 111.26(18) . . ?
O10 C11 C15 108.00(18) . . ?
O12 C11 C15 104.34(17) . . ?
O12 C13 O14 104.09(16) . . ?
O12 C13 C131 110.0(2) . . ?
O14 C13 C131 108.38(18) . . ?
O12 C13 C132 110.10(18) . . ?
O14 C13 C132 110.59(19) . . ?
C131 C13 C132 113.28(19) . . ?
O14 C15 C16 111.45(17) . . ?
O14 C15 C11 104.71(17) . . ?
C16 C15 C11 104.64(18) . . ?
O16 C16 C15 110.24(18) . . ?
O16 C16 C7 110.26(17) . . ?
C15 C16 C7 104.45(17) . . ?
O16 C17 C171 111.10(18) . . ?
C32 C31 C36 118.6(2) . . ?
C32 C31 C10 122.2(2) . . ?
C36 C31 C10 119.2(2) . . ?
C31 C32 C33 120.9(2) . . ?
C34 C33 C32 119.7(2) . . ?
C33 C34 C35 120.0(2) . . ?
C34 C35 C36 120.2(2) . . ?
C35 C36 C31 120.7(2) . . ?
C176 C171 C172 118.8(2) . . ?
C176 C171 C17 121.8(2) . . ?
C172 C171 C17 119.3(2) . . ?
C173 C172 C171 121.0(2) . . ?
C172 C173 C174 119.6(2) . . ?
C175 C174 C173 120.0(2) . . ?
C174 C175 C176 120.6(2) . . ?
C171 C176 C175 120.0(2) . . ?
C3 O2 N1 110.48(16) . . ?
C6 O5 C4 115.38(18) . . ?
C11 O10 C7 111.09(16) . . ?
C11 O12 C13 107.94(17) . . ?
C15 O14 C13 106.61(16) . . ?
C17 O16 C16 111.79(16) . . ?
O2 N1 C8 104.83(17) . . ?
O2 N1 C10 106.19(17) . . ?
C8 N1 C10 111.81(17) . . ?
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
C3 O2 1.455(3) . ?
C3 C4 1.514(4) . ?
C3 C9 1.516(3) . ?
C4 O5 1.421(3) . ?
C6 O5 1.417(3) . ?
C6 C7 1.535(3) . ?
C7 O10 1.450(2) . ?
C7 C8 1.527(3) . ?
C7 C16 1.543(3) . ?
C8 N1 1.471(3) . ?
C8 C9 1.530(3) . ?
C10 N1 1.477(3) . ?
C10 C31 1.508(3) . ?
C11 O10 1.400(3) . ?
C11 O12 1.427(3) . ?
C11 C15 1.541(3) . ?
C13 O12 1.427(3) . ?
C13 O14 1.437(3) . ?
C13 C131 1.501(3) . ?
C13 C132 1.525(3) . ?
C15 O14 1.427(3) . ?
C15 C16 1.530(3) . ?
C16 O16 1.423(3) . ?
C17 O16 1.419(3) . ?
C17 C171 1.499(3) . ?
C31 C32 1.386(3) . ?
C31 C36 1.389(3) . ?
C32 C33 1.395(3) . ?
C33 C34 1.376(4) . ?
C34 C35 1.382(4) . ?
C35 C36 1.385(4) . ?
C171 C176 1.391(3) . ?
C171 C172 1.395(3) . ?
C172 C173 1.384(3) . ?
C173 C174 1.392(4) . ?
C174 C175 1.372(4) . ?
C175 C176 1.395(3) . ?
O2 N1 1.464(3) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C3 C4 O5 -85.6(2) . . . . ?
C9 C3 C4 O5 31.0(3) . . . . ?
O5 C6 C7 O10 -55.9(2) . . . . ?
O5 C6 C7 C8 62.2(2) . . . . ?
O5 C6 C7 C16 -170.06(17) . . . . ?
O10 C7 C8 N1 -178.43(17) . . . . ?
C6 C7 C8 N1 60.1(2) . . . . ?
C16 C7 C8 N1 -64.9(2) . . . . ?
O10 C7 C8 C9 64.3(2) . . . . ?
C6 C7 C8 C9 -57.2(2) . . . . ?
C16 C7 C8 C9 177.85(18) . . . . ?
O2 C3 C9 C8 26.4(2) . . . . ?
C4 C3 C9 C8 -92.1(2) . . . . ?
N1 C8 C9 C3 -34.4(2) . . . . ?
C7 C8 C9 C3 85.2(2) . . . . ?
O10 C11 C15 O14 114.78(19) . . . . ?
O12 C11 C15 O14 -3.7(2) . . . . ?
O10 C11 C15 C16 -2.6(2) . . . . ?
O12 C11 C15 C16 -121.03(18) . . . . ?
O14 C15 C16 O16 146.66(18) . . . . ?
C11 C15 C16 O16 -100.7(2) . . . . ?
O14 C15 C16 C7 -94.9(2) . . . . ?
C11 C15 C16 C7 17.7(2) . . . . ?
O10 C7 C16 O16 91.94(19) . . . . ?
C8 C7 C16 O16 -22.0(2) . . . . ?
C6 C7 C16 O16 -149.61(18) . . . . ?
O10 C7 C16 C15 -26.5(2) . . . . ?
C8 C7 C16 C15 -140.40(18) . . . . ?
C6 C7 C16 C15 92.0(2) . . . . ?
N1 C10 C31 C32 -119.5(2) . . . . ?
N1 C10 C31 C36 61.1(3) . . . . ?
C36 C31 C32 C33 1.0(4) . . . . ?
C10 C31 C32 C33 -178.4(2) . . . . ?
C31 C32 C33 C34 0.1(4) . . . . ?
C32 C33 C34 C35 -0.8(4) . . . . ?
C33 C34 C35 C36 0.4(4) . . . . ?
C34 C35 C36 C31 0.8(4) . . . . ?
C32 C31 C36 C35 -1.4(4) . . . . ?
C10 C31 C36 C35 178.0(2) . . . . ?
O16 C17 C171 C176 5.5(3) . . . . ?
O16 C17 C171 C172 -170.7(2) . . . . ?
C176 C171 C172 C173 -0.7(3) . . . . ?
C17 C171 C172 C173 175.6(2) . . . . ?
C171 C172 C173 C174 -0.3(3) . . . . ?
C172 C173 C174 C175 1.1(4) . . . . ?
C173 C174 C175 C176 -1.0(4) . . . . ?
C172 C171 C176 C175 0.9(3) . . . . ?
C17 C171 C176 C175 -175.3(2) . . . . ?
C174 C175 C176 C171 0.0(3) . . . . ?
C4 C3 O2 N1 111.4(2) . . . . ?
C9 C3 O2 N1 -9.6(2) . . . . ?
C7 C6 O5 C4 -90.3(2) . . . . ?
C3 C4 O5 C6 55.7(3) . . . . ?
O12 C11 O10 C7 98.7(2) . . . . ?
C15 C11 O10 C7 -15.2(2) . . . . ?
C8 C7 O10 C11 146.47(18) . . . . ?
C6 C7 O10 C11 -90.4(2) . . . . ?
C16 C7 O10 C11 26.4(2) . . . . ?
O10 C11 O12 C13 -134.21(18) . . . . ?
C15 C11 O12 C13 -18.0(2) . . . . ?
O14 C13 O12 C11 33.0(2) . . . . ?
C131 C13 O12 C11 148.94(18) . . . . ?
C132 C13 O12 C11 -85.5(2) . . . . ?
C16 C15 O14 C13 136.37(19) . . . . ?
C11 C15 O14 C13 23.8(2) . . . . ?
O12 C13 O14 C15 -35.3(2) . . . . ?
C131 C13 O14 C15 -152.31(19) . . . . ?
C132 C13 O14 C15 83.0(2) . . . . ?
C171 C17 O16 C16 171.43(18) . . . . ?
C15 C16 O16 C17 -83.2(2) . . . . ?
C7 C16 O16 C17 162.01(17) . . . . ?
C3 O2 N1 C8 -12.2(2) . . . . ?
C3 O2 N1 C10 106.3(2) . . . . ?
C7 C8 N1 O2 -93.3(2) . . . . ?
C9 C8 N1 O2 29.0(2) . . . . ?
C7 C8 N1 C10 152.1(2) . . . . ?
C9 C8 N1 C10 -85.6(2) . . . . ?
C31 C10 N1 O2 73.8(2) . . . . ?
C31 C10 N1 C8 -172.4(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21194012
