#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/08/7150840.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_7150840
loop_
_publ_author_name
'Anegundi, Ramakrishna I.'
'Puranik, Vedavati G.'
'Hotha, Srinivas'
_publ_section_title
;
 Synthesis of 1,2,3-triazole and 1,2,3,4-tetrazole-fused glycosides and
 nucleosides by an intramolecular 1,3-dipolar cycloaddition reaction
;
_journal_issue                   4
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              779
_journal_page_last               786
_journal_paper_doi               10.1039/b716996e
_journal_volume                  6
_journal_year                    2008
_chemical_formula_moiety         'C11 H15 N3 O4'
_chemical_formula_sum            'C11 H15 N3 O4'
_chemical_formula_weight         253.26
_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                   5.495(1)
_cell_length_b                   10.054(2)
_cell_length_c                   21.330(4)
_cell_measurement_temperature    293(2)
_cell_volume                     1178.4(4)
_computing_cell_refinement       SMART
_computing_data_collection       SMART
_computing_data_reduction        SAINTPLUS
_computing_structure_refinement  'SHELXTL (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX CCD Area detector'
_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  0.0597
_diffrn_reflns_av_sigmaI/netI    0.1284
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5138
_diffrn_reflns_theta_full        23.27
_diffrn_reflns_theta_max         23.27
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.110
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle-like
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.099
_refine_diff_density_min         -0.091
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2.1(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.541
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         1686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.541
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0306
_refine_ls_wR_factor_ref         0.0357
_reflns_number_gt                920
_reflns_number_total             1686
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b716996e.txt
_cod_data_source_block           datam
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7150840
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
C1 C -0.0438(6) 0.1828(3) 0.85770(16) 0.0458(9) Uani 1 1 d . . .
C2 C 0.1565(6) 0.1731(3) 0.90690(14) 0.0389(9) Uani 1 1 d . . .
C3 C 0.2329(6) 0.3164(3) 0.91846(16) 0.0391(8) Uani 1 1 d . . .
C4 C 0.1541(6) 0.3806(3) 0.85675(14) 0.0402(8) Uani 1 1 d . . .
C5 C 0.1261(7) 0.5290(3) 0.85046(17) 0.0415(9) Uani 1 1 d . . .
C6 C 0.1309(7) 0.4929(3) 0.99041(15) 0.0450(10) Uani 1 1 d . . .
C7 C -0.0488(7) 0.5767(3) 0.95709(14) 0.0399(9) Uani 1 1 d . . .
C8 C -0.2462(7) 0.6496(3) 0.97486(17) 0.0492(10) Uani 1 1 d . . .
C13 C 0.4282(9) 0.0292(5) 0.77318(19) 0.0633(12) Uani 1 1 d . . .
C14 C 0.2451(7) 0.0327(3) 0.82371(15) 0.0441(9) Uani 1 1 d . . .
C15 C 0.1520(10) -0.1032(4) 0.8437(2) 0.0680(12) Uani 1 1 d . . .
N16 N -0.0532(5) 0.5855(2) 0.89399(12) 0.0409(7) Uani 1 1 d . . .
N17 N -0.2413(5) 0.6587(2) 0.87325(12) 0.0511(8) Uani 1 1 d . . .
N18 N -0.3586(5) 0.6994(2) 0.92397(15) 0.0562(8) Uani 1 1 d . . .
O9 O -0.0735(4) 0.31862(18) 0.84266(8) 0.0442(6) Uani 1 1 d . . .
O10 O 0.0429(4) 0.11229(19) 0.80531(8) 0.0461(6) Uani 1 1 d . . .
O11 O 0.3473(4) 0.10268(17) 0.87637(8) 0.0454(6) Uani 1 1 d . . .
O12 O 0.1038(4) 0.35618(17) 0.97313(8) 0.0464(6) Uani 1 1 d . . .
H1 H -0.195(5) 0.151(2) 0.8700(12) 0.038(10) Uiso 1 1 d . . .
H2 H 0.096(4) 0.1301(19) 0.9455(9) 0.018(7) Uiso 1 1 d . . .
H3 H 0.397(4) 0.3234(19) 0.9247(9) 0.008(7) Uiso 1 1 d . . .
H4 H 0.285(5) 0.349(2) 0.8234(10) 0.053(10) Uiso 1 1 d . . .
H8 H -0.288(5) 0.664(2) 1.0194(10) 0.046(9) Uiso 1 1 d . . .
H51 H 0.269(5) 0.571(2) 0.8602(11) 0.031(9) Uiso 1 1 d . . .
H52 H 0.072(4) 0.559(2) 0.8083(10) 0.036(8) Uiso 1 1 d . . .
H61 H 0.100(4) 0.495(2) 1.0371(9) 0.032(8) Uiso 1 1 d . . .
H62 H 0.297(5) 0.526(2) 0.9790(11) 0.040(9) Uiso 1 1 d . . .
H131 H 0.579(7) -0.010(3) 0.7901(14) 0.114(16) Uiso 1 1 d . . .
H132 H 0.363(5) -0.007(2) 0.7396(10) 0.048(10) Uiso 1 1 d . . .
H133 H 0.496(6) 0.125(3) 0.7639(13) 0.098(14) Uiso 1 1 d . . .
H151 H 0.032(6) -0.102(3) 0.8771(13) 0.101(17) Uiso 1 1 d . . .
H152 H 0.280(5) -0.147(3) 0.8539(13) 0.049(13) Uiso 1 1 d . . .
H153 H 0.071(6) -0.148(3) 0.8003(13) 0.102(12) Uiso 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O10 C1 O9 110.2(3) . . ?
O10 C1 C2 105.7(3) . . ?
O9 C1 C2 107.5(3) . . ?
O10 C1 H1 110.9(16) . . ?
O9 C1 H1 106.9(16) . . ?
C2 C1 H1 115.5(17) . . ?
O11 C2 C3 110.0(3) . . ?
O11 C2 C1 104.4(2) . . ?
C3 C2 C1 104.5(3) . . ?
O11 C2 H2 114.4(13) . . ?
C3 C2 H2 111.9(12) . . ?
C1 C2 H2 110.9(13) . . ?
O12 C3 C2 105.2(3) . . ?
O12 C3 C4 116.5(3) . . ?
C2 C3 C4 100.5(3) . . ?
O12 C3 H3 110.5(13) . . ?
C2 C3 H3 111.7(13) . . ?
C4 C3 H3 111.9(14) . . ?
O9 C4 C5 108.9(3) . . ?
O9 C4 C3 104.2(2) . . ?
C5 C4 C3 121.6(3) . . ?
O9 C4 H4 109.0(14) . . ?
C5 C4 H4 107.6(13) . . ?
C3 C4 H4 105.0(14) . . ?
N16 C5 C4 113.3(3) . . ?
N16 C5 H51 104.7(16) . . ?
C4 C5 H51 110.5(15) . . ?
N16 C5 H52 104.7(13) . . ?
C4 C5 H52 114.4(13) . . ?
H51 C5 H52 109(2) . . ?
O12 C6 C7 110.7(3) . . ?
O12 C6 H61 104.8(12) . . ?
C7 C6 H61 110.6(14) . . ?
O12 C6 H62 110.4(14) . . ?
C7 C6 H62 107.7(15) . . ?
H61 C6 H62 113(2) . . ?
N16 C7 C8 103.2(3) . . ?
N16 C7 C6 121.9(3) . . ?
C8 C7 C6 134.7(3) . . ?
N18 C8 C7 109.9(3) . . ?
N18 C8 H8 127.7(15) . . ?
C7 C8 H8 122.3(15) . . ?
C14 C13 H131 108(2) . . ?
C14 C13 H132 109(2) . . ?
H131 C13 H132 118(3) . . ?
C14 C13 H133 110.9(18) . . ?
H131 C13 H133 98(3) . . ?
H132 C13 H133 112(3) . . ?
O10 C14 O11 104.2(2) . . ?
O10 C14 C13 110.1(3) . . ?
O11 C14 C13 108.4(3) . . ?
O10 C14 C15 108.6(3) . . ?
O11 C14 C15 110.6(3) . . ?
C13 C14 C15 114.4(4) . . ?
C14 C15 H151 115(2) . . ?
C14 C15 H152 105(2) . . ?
H151 C15 H152 112(3) . . ?
C14 C15 H153 105.1(15) . . ?
H151 C15 H153 110(3) . . ?
H152 C15 H153 109(3) . . ?
N17 N16 C7 112.2(3) . . ?
N17 N16 C5 121.3(3) . . ?
C7 N16 C5 126.4(3) . . ?
N18 N17 N16 105.9(2) . . ?
N17 N18 C8 108.7(3) . . ?
C1 O9 C4 105.8(2) . . ?
C1 O10 C14 109.2(2) . . ?
C2 O11 C14 108.2(2) . . ?
C3 O12 C6 115.4(2) . . ?
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
C1 O10 1.406(3) . ?
C1 O9 1.412(3) . ?
C1 C2 1.524(4) . ?
C1 H1 0.93(2) . ?
C2 O11 1.423(3) . ?
C2 C3 1.520(4) . ?
C2 H2 0.988(19) . ?
C3 O12 1.423(3) . ?
C3 C4 1.529(4) . ?
C3 H3 0.91(2) . ?
C4 O9 1.429(3) . ?
C4 C5 1.505(4) . ?
C4 H4 1.06(2) . ?
C5 N16 1.468(4) . ?
C5 H51 0.92(2) . ?
C5 H52 0.995(19) . ?
C6 O12 1.431(3) . ?
C6 C7 1.480(4) . ?
C6 H61 1.011(18) . ?
C6 H62 1.00(3) . ?
C7 N16 1.349(3) . ?
C7 C8 1.363(4) . ?
C8 N18 1.345(4) . ?
C8 H8 0.99(2) . ?
C13 C14 1.475(5) . ?
C13 H131 0.99(3) . ?
C13 H132 0.88(2) . ?
C13 H133 1.05(3) . ?
C14 O10 1.424(3) . ?
C14 O11 1.439(3) . ?
C14 C15 1.520(5) . ?
C15 H151 0.97(3) . ?
C15 H152 0.86(3) . ?
C15 H153 1.12(3) . ?
N16 N17 1.344(3) . ?
N17 N18 1.324(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21195399
