#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:58:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180325 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/39/7153992.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_7153992
loop_
_publ_author_name
'Putapatri, Siddamal Reddy'
'Kanwal, Abhinav'
'Sridhar, Balasubramanian'
'Banerjee, Sanjay K.'
'Kantevari, Srinivas'
_publ_section_title
;
 Synthesis of l-rhamnose derived chiral bicyclic triazoles as novel
 sodium-glucose transporter (SGLT) inhibitors.
;
_journal_issue                   42
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8415
_journal_page_last               8421
_journal_paper_doi               10.1039/c4ob01319k
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C13 H15 N3 O3'
_chemical_formula_sum            'C13 H15 N3 O3'
_chemical_formula_weight         261.28
_chemical_name_systematic
; 
(4S,5R,6S,7R)-7-methyl-3-phenyl-4,5,6,7-tetrahydro-[1,2,3]triazolo
[1,5-a]pyridine-4,5,6-triol 
;
_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                   7.0280(11)
_cell_length_b                   12.5922(19)
_cell_length_c                   14.037(2)
_cell_measurement_reflns_used    7068
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.98
_cell_measurement_theta_min      2.90
_cell_volume                     1242.2(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'ω 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  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0114
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11307
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         1285
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0277
_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)+(0.0481P)²+0.1129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0727
_reflns_number_gt                1239
_reflns_number_total             1285
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c4ob01319k2.cif
_cod_data_source_block           as42m
_cod_depositor_comments
'Adding full bibliography for 7153992--7153993.cif.'
_cod_database_code               7153992
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
C1 C 0.1025(2) 0.78074(12) 0.70865(11) 0.0325(4) Uani 1 1 d .
C2 C -0.1077(2) 0.75761(13) 0.71144(13) 0.0366(4) Uani 1 1 d .
H2 H -0.1394 0.7096 0.6588 0.044 Uiso 1 1 calc R
C3 C -0.1677(3) 0.70526(14) 0.80581(14) 0.0446(4) Uani 1 1 d .
H3 H -0.2853 0.6651 0.7952 0.053 Uiso 1 1 calc R
C4 C -0.0159(3) 0.62982(14) 0.84285(14) 0.0447(4) Uani 1 1 d .
H4 H -0.0631 0.5939 0.9001 0.054 Uiso 1 1 calc R
C5 C 0.1664(3) 0.69085(13) 0.86719(12) 0.0397(4) Uani 1 1 d .
H5 H 0.1384 0.7416 0.9183 0.048 Uiso 1 1 calc R
C6 C 0.2203(2) 0.82991(12) 0.64364(13) 0.0341(4) Uani 1 1 d .
C7 C 0.1817(3) 0.87999(12) 0.55057(11) 0.0387(4) Uani 1 1 d .
C8 C 0.0100(3) 0.86535(15) 0.50278(13) 0.0515(5) Uani 1 1 d .
H8 H -0.0823 0.8208 0.5284 0.062 Uiso 1 1 calc R
C9 C -0.0239(4) 0.91700(17) 0.41712(14) 0.0661(6) Uani 1 1 d .
H9 H -0.1390 0.9070 0.3857 0.079 Uiso 1 1 calc R
C10 C 0.1117(5) 0.98275(16) 0.37852(15) 0.0752(8) Uani 1 1 d .
H10 H 0.0881 1.0177 0.3213 0.090 Uiso 1 1 calc R
C11 C 0.2810(5) 0.99666(18) 0.42437(15) 0.0725(8) Uani 1 1 d .
H11 H 0.3729 1.0409 0.3980 0.087 Uiso 1 1 calc R
C12 C 0.3173(3) 0.94562(15) 0.50951(13) 0.0540(5) Uani 1 1 d .
H12 H 0.4338 0.9553 0.5396 0.065 Uiso 1 1 calc R
C13 C 0.3271(3) 0.61918(17) 0.89905(14) 0.0520(5) Uani 1 1 d .
H13A H 0.4340 0.6617 0.9179 0.078 Uiso 1 1 calc R
H13B H 0.3636 0.5735 0.8474 0.078 Uiso 1 1 calc R
H13C H 0.2856 0.5769 0.9520 0.078 Uiso 1 1 calc R
N1 N 0.21827(18) 0.75062(11) 0.78006(10) 0.0342(3) Uani 1 1 d .
N2 N 0.3989(2) 0.77883(11) 0.76299(11) 0.0401(3) Uani 1 1 d .
N3 N 0.4003(2) 0.82745(12) 0.67996(11) 0.0394(3) Uani 1 1 d .
O1 O -0.20417(18) 0.85623(9) 0.69706(11) 0.0465(3) Uani 1 1 d .
O2 O -0.2002(2) 0.78144(13) 0.87797(11) 0.0632(4) Uani 1 1 d .
O3 O 0.0149(2) 0.55408(10) 0.77027(10) 0.0561(4) Uani 1 1 d .
H1O H -0.317(4) 0.8465(18) 0.6829(15) 0.055(6) Uiso 1 1 d .
H3O H 0.066(4) 0.5002(17) 0.7916(16) 0.071(7) Uiso 1 1 d .
H2O H -0.281(4) 0.824(2) 0.861(2) 0.085(9) 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
N1 C1 C6 104.86(14)
N1 C1 C2 121.28(15)
C6 C1 C2 133.86(16)
O1 C2 C1 107.07(13)
O1 C2 C3 111.35(15)
C1 C2 C3 111.95(15)
O1 C2 H2 108.8
C1 C2 H2 108.8
C3 C2 H2 108.8
O2 C3 C4 107.01(16)
O2 C3 C2 111.74(14)
C4 C3 C2 111.72(15)
O2 C3 H3 108.8
C4 C3 H3 108.8
C2 C3 H3 108.8
O3 C4 C3 106.43(15)
O3 C4 C5 111.80(15)
C3 C4 C5 110.46(14)
O3 C4 H4 109.4
C3 C4 H4 109.4
C5 C4 H4 109.4
N1 C5 C13 111.31(15)
N1 C5 C4 106.04(13)
C13 C5 C4 113.00(15)
N1 C5 H5 108.8
C13 C5 H5 108.8
C4 C5 H5 108.8
N3 C6 C1 107.41(15)
N3 C6 C7 120.75(15)
C1 C6 C7 131.84(16)
C12 C7 C8 118.29(17)
C12 C7 C6 119.74(17)
C8 C7 C6 121.95(16)
C9 C8 C7 120.3(2)
C9 C8 H8 119.9
C7 C8 H8 119.9
C10 C9 C8 120.3(2)
C10 C9 H9 119.8
C8 C9 H9 119.8
C11 C10 C9 119.8(2)
C11 C10 H10 120.1
C9 C10 H10 120.1
C10 C11 C12 120.6(2)
C10 C11 H11 119.7
C12 C11 H11 119.7
C11 C12 C7 120.7(2)
C11 C12 H12 119.7
C7 C12 H12 119.7
C5 C13 H13A 109.5
C5 C13 H13B 109.5
H13A C13 H13B 109.5
C5 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
N2 N1 C1 111.41(13)
N2 N1 C5 121.02(13)
C1 N1 C5 127.55(14)
N3 N2 N1 106.78(13)
N2 N3 C6 109.54(13)
C2 O1 H1O 111.1(16)
C3 O2 H2O 111(2)
C4 O3 H3O 111.1(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.346(2)
C1 C6 1.379(2)
C1 C2 1.506(2)
C2 O1 1.429(2)
C2 C3 1.539(2)
C2 H2 0.9800
C3 O2 1.414(2)
C3 C4 1.520(2)
C3 H3 0.9800
C4 O3 1.412(2)
C4 C5 1.533(2)
C4 H4 0.9800
C5 N1 1.482(2)
C5 C13 1.513(2)
C5 H5 0.9800
C6 N3 1.364(2)
C6 C7 1.476(2)
C7 C12 1.387(3)
C7 C8 1.393(3)
C8 C9 1.388(3)
C8 H8 0.9300
C9 C10 1.374(4)
C9 H9 0.9300
C10 C11 1.364(4)
C10 H10 0.9300
C11 C12 1.381(3)
C11 H11 0.9300
C12 H12 0.9300
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
N1 N2 1.3397(19)
N2 N3 1.317(2)
O1 H1O 0.83(2)
O2 H2O 0.82(3)
O3 H3O 0.82(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2O N2 0.82(3) 2.70(3) 3.247(2) 126(2) 1_455
O3 H3O O1 0.82(2) 2.06(2) 2.8612(18) 163(2) 3_546
O1 H1O N3 0.83(2) 2.00(3) 2.814(2) 167(2) 1_455
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
N1 C1 C2 O1 126.37(15)
C6 C1 C2 O1 -54.3(3)
N1 C1 C2 C3 4.1(2)
C6 C1 C2 C3 -176.60(16)
O1 C2 C3 O2 -36.0(2)
C1 C2 C3 O2 83.85(19)
O1 C2 C3 C4 -155.84(14)
C1 C2 C3 C4 -36.0(2)
O2 C3 C4 O3 179.86(14)
C2 C3 C4 O3 -57.52(18)
O2 C3 C4 C5 -58.59(19)
C2 C3 C4 C5 64.0(2)
O3 C4 C5 N1 63.89(16)
C3 C4 C5 N1 -54.43(19)
O3 C4 C5 C13 -58.3(2)
C3 C4 C5 C13 -176.62(15)
N1 C1 C6 N3 -0.52(18)
C2 C1 C6 N3 -179.92(18)
N1 C1 C6 C7 179.94(15)
C2 C1 C6 C7 0.5(3)
N3 C6 C7 C12 -14.7(2)
C1 C6 C7 C12 164.81(18)
N3 C6 C7 C8 166.73(16)
C1 C6 C7 C8 -13.8(3)
C12 C7 C8 C9 -1.1(3)
C6 C7 C8 C9 177.55(17)
C7 C8 C9 C10 0.2(3)
C8 C9 C10 C11 0.5(3)
C9 C10 C11 C12 -0.3(3)
C10 C11 C12 C7 -0.6(3)
C8 C7 C12 C11 1.3(3)
C6 C7 C12 C11 -177.37(17)
C6 C1 N1 N2 0.36(18)
C2 C1 N1 N2 179.86(15)
C6 C1 N1 C5 -177.73(14)
C2 C1 N1 C5 1.8(2)
C13 C5 N1 N2 -31.1(2)
C4 C5 N1 N2 -154.40(15)
C13 C5 N1 C1 146.80(17)
C4 C5 N1 C1 23.5(2)
C1 N1 N2 N3 -0.05(18)
C5 N1 N2 N3 178.18(13)
N1 N2 N3 C6 -0.29(18)
C1 C6 N3 N2 0.51(18)
C7 C6 N3 N2 -179.89(13)
