#------------------------------------------------------------------------------
#$Date: 2025-08-19 23:06:29 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301812 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/72/4027258.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_4027258
loop_
_publ_author_name
'Bharat P. Gurale'
'Mysore S. Shashidhar'
'Rajesh G. Gonnade'
_publ_section_title
;
 Synthesis of the Aminocyclitol Units of (-)-Hygromycin A and
 Methoxyhygromycin from myo-Inositol
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5801
_journal_page_last               5807
_journal_paper_doi               10.1021/jo300444b
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C17 H25 N O10'
_chemical_formula_sum            'C17 H25 N O10'
_chemical_formula_weight         403.38
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_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                 103.406(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.345(2)
_cell_length_b                   11.1876(18)
_cell_length_c                   12.2187(19)
_cell_measurement_reflns_used    5215
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28.116
_cell_measurement_theta_min      2.275
_cell_volume                     2040.5(5)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    'SHELXTL, ORTEP3,MERCURY1.2.1'
_computing_publication_material  'SHELXTL, PLATON'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'BRUKER SMART APEX'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'Omega and phi 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  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7131
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9681
_exptl_absorpt_correction_T_min  0.9405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       rhombus
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         3525
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0351
_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)+(0.0467P)²+0.7377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0894
_reflns_number_gt                3475
_reflns_number_total             3525
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300444b_si_007.cif
_cod_data_source_block           compound_20
_cod_original_cell_volume        2040.5(6)
_cod_database_code               4027258
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, 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
O1 O 0.44925(9) 0.24588(13) 0.39432(11) 0.0319(3) Uani 1 1 d .
O3 O 0.21376(9) 0.53006(12) 0.23783(10) 0.0313(3) Uani 1 1 d .
O4 O 0.08774(9) 0.35654(13) 0.23926(11) 0.0319(3) Uani 1 1 d .
O5 O 0.19252(9) 0.15781(13) 0.21178(11) 0.0329(3) Uani 1 1 d .
O6 O 0.32346(9) 0.07357(12) 0.39748(11) 0.0326(3) Uani 1 1 d .
O7 O 0.49818(11) 0.1684(2) 0.25020(13) 0.0633(6) Uani 1 1 d .
O8 O 0.46732(16) 0.5698(2) 0.34473(18) 0.0823(8) Uani 1 1 d .
O9 O 0.26121(11) 0.55449(15) 0.07947(12) 0.0448(4) Uani 1 1 d .
O10 O 0.03597(10) 0.38449(17) 0.39514(12) 0.0475(4) Uani 1 1 d .
O11 O 0.24473(10) 0.04972(14) 0.52885(13) 0.0413(4) Uani 1 1 d .
N1 N 0.36375(11) 0.46252(14) 0.40452(14) 0.0291(3) Uani 1 1 d .
C1 C 0.36009(12) 0.25805(17) 0.32464(15) 0.0268(4) Uani 1 1 d .
C2 C 0.33888(13) 0.39107(18) 0.30296(15) 0.0285(4) Uani 1 1 d .
C3 C 0.23954(13) 0.40630(18) 0.24357(15) 0.0279(4) Uani 1 1 d .
C4 C 0.17801(12) 0.34365(17) 0.30594(15) 0.0270(4) Uani 1 1 d .
C5 C 0.20018(13) 0.21134(18) 0.31969(15) 0.0277(4) Uani 1 1 d .
C6 C 0.29700(12) 0.19760(18) 0.38685(15) 0.0274(4) Uani 1 1 d .
C7 C 0.51225(13) 0.1967(2) 0.34748(17) 0.0363(5) Uani 1 1 d .
C8 C 0.59845(15) 0.1812(3) 0.4343(2) 0.0525(6) Uani 1 1 d .
H8A H 0.6429 0.1431 0.3997 0.079 Uiso 1 1 calc R
H8B H 0.5880 0.1308 0.4956 0.079 Uiso 1 1 calc R
H8C H 0.6207 0.2596 0.4642 0.079 Uiso 1 1 calc R
C9 C 0.42729(15) 0.54791(19) 0.41701(18) 0.0392(5) Uani 1 1 d .
C10 C 0.44593(16) 0.6130(2) 0.52799(19) 0.0432(5) Uani 1 1 d .
H10A H 0.4723 0.5575 0.5887 0.065 Uiso 1 1 calc R
H10B H 0.3898 0.6452 0.5411 0.065 Uiso 1 1 calc R
H10C H 0.4878 0.6788 0.5264 0.065 Uiso 1 1 calc R
C11 C 0.22507(13) 0.59387(19) 0.14899(16) 0.0326(4) Uani 1 1 d .
C12 C 0.18585(16) 0.7154(2) 0.1484(2) 0.0443(5) Uani 1 1 d .
H12A H 0.2252 0.7651 0.2052 0.066 Uiso 1 1 calc R
H12B H 0.1267 0.7097 0.1656 0.066 Uiso 1 1 calc R
H12C H 0.1798 0.7516 0.0739 0.066 Uiso 1 1 calc R
C13 C 0.02249(13) 0.37387(19) 0.29493(18) 0.0355(5) Uani 1 1 d .
C14 C -0.06745(16) 0.3742(3) 0.2144(2) 0.0521(6) Uani 1 1 d .
H14A H -0.0937 0.2941 0.2108 0.078 Uiso 1 1 calc R
H14B H -0.0607 0.3975 0.1395 0.078 Uiso 1 1 calc R
H14C H -0.1068 0.4313 0.2402 0.078 Uiso 1 1 calc R
C15 C 0.11922(16) 0.0790(2) 0.1779(2) 0.0488(6) Uani 1 1 d .
H15A H 0.1227 0.0159 0.2344 0.073 Uiso 1 1 calc R
H15B H 0.1211 0.0430 0.1053 0.073 Uiso 1 1 calc R
H15C H 0.0631 0.1234 0.1705 0.073 Uiso 1 1 calc R
C16 C 0.29239(13) 0.00889(19) 0.47378(16) 0.0336(4) Uani 1 1 d .
C17 C 0.32744(18) -0.1158(2) 0.4813(2) 0.0485(6) Uani 1 1 d .
H17A H 0.2991 -0.1626 0.5314 0.073 Uiso 1 1 calc R
H17B H 0.3925 -0.1147 0.5113 0.073 Uiso 1 1 calc R
H17C H 0.3138 -0.1520 0.4063 0.073 Uiso 1 1 calc R
H1 H 0.3549(13) 0.2200(17) 0.2563(18) 0.019(5) Uiso 1 1 d .
H2 H 0.3741(14) 0.4209(18) 0.2543(17) 0.022(5) Uiso 1 1 d .
H3 H 0.2281(15) 0.376(2) 0.170(2) 0.030(5) Uiso 1 1 d .
H4 H 0.1835(13) 0.3751(16) 0.3787(18) 0.016(4) Uiso 1 1 d .
H5 H 0.1595(15) 0.1718(19) 0.3593(19) 0.026(5) Uiso 1 1 d .
H6 H 0.3029(12) 0.2324(16) 0.4567(17) 0.014(4) Uiso 1 1 d .
H1N H 0.3367(18) 0.445(2) 0.449(2) 0.041(7) 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'
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
C7 O1 C1 117.61(15)
C11 O3 C3 117.76(15)
C13 O4 C4 117.23(14)
C15 O5 C5 114.94(15)
C16 O6 C6 116.10(15)
C9 N1 C2 121.81(17)
O1 C1 C6 106.86(15)
O1 C1 C2 109.17(15)
C6 C1 C2 112.56(15)
N1 C2 C1 112.57(15)
N1 C2 C3 112.20(16)
C1 C2 C3 109.66(16)
O3 C3 C4 105.88(14)
O3 C3 C2 111.17(16)
C4 C3 C2 112.10(15)
O4 C4 C3 107.36(14)
O4 C4 C5 108.72(15)
C3 C4 C5 110.89(15)
O5 C5 C4 109.76(15)
O5 C5 C6 108.36(15)
C4 C5 C6 108.78(15)
O6 C6 C1 105.90(14)
O6 C6 C5 111.28(16)
C1 C6 C5 109.81(15)
O7 C7 O1 123.05(19)
O7 C7 C8 126.6(2)
O1 C7 C8 110.37(17)
O8 C9 N1 122.4(2)
O8 C9 C10 122.4(2)
N1 C9 C10 115.20(18)
O9 C11 O3 122.95(19)
O9 C11 C12 125.80(18)
O3 C11 C12 111.24(17)
O10 C13 O4 123.82(18)
O10 C13 C14 125.80(19)
O4 C13 C14 110.36(18)
O11 C16 O6 122.99(18)
O11 C16 C17 125.65(19)
O6 C16 C17 111.34(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.350(2)
O1 C1 1.440(2)
O3 C11 1.344(2)
O3 C3 1.437(2)
O4 C13 1.349(2)
O4 C4 1.442(2)
O5 C15 1.414(3)
O5 C5 1.428(2)
O6 C16 1.351(2)
O6 C6 1.443(2)
O7 C7 1.200(3)
O8 C9 1.212(3)
O9 C11 1.201(3)
O10 C13 1.200(3)
O11 C16 1.193(2)
N1 C9 1.348(3)
N1 C2 1.451(2)
C1 C6 1.521(3)
C1 C2 1.533(3)
C2 C3 1.538(3)
C3 C4 1.516(3)
C4 C5 1.519(3)
C5 C6 1.529(3)
C7 C8 1.501(3)
C9 C10 1.507(3)
C11 C12 1.487(3)
C13 C14 1.498(3)
C16 C17 1.490(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
C7 O1 C1 C6 125.96(17)
C7 O1 C1 C2 -112.05(18)
C9 N1 C2 C1 116.2(2)
C9 N1 C2 C3 -119.5(2)
O1 C1 C2 N1 -46.1(2)
C6 C1 C2 N1 72.4(2)
O1 C1 C2 C3 -171.75(14)
C6 C1 C2 C3 -53.27(19)
C11 O3 C3 C4 -149.94(16)
C11 O3 C3 C2 88.07(19)
N1 C2 C3 O3 45.0(2)
C1 C2 C3 O3 170.86(13)
N1 C2 C3 C4 -73.3(2)
C1 C2 C3 C4 52.6(2)
C13 O4 C4 C3 -142.42(17)
C13 O4 C4 C5 97.56(19)
O3 C3 C4 O4 62.56(18)
C2 C3 C4 O4 -176.05(15)
O3 C3 C4 C5 -178.80(14)
C2 C3 C4 C5 -57.4(2)
C15 O5 C5 C4 -109.9(2)
C15 O5 C5 C6 131.44(19)
O4 C4 C5 O5 59.61(18)
C3 C4 C5 O5 -58.20(19)
O4 C4 C5 C6 178.02(14)
C3 C4 C5 C6 60.21(18)
C16 O6 C6 C1 163.84(15)
C16 O6 C6 C5 -76.9(2)
O1 C1 C6 O6 -61.98(18)
C2 C1 C6 O6 178.19(14)
O1 C1 C6 C5 177.77(15)
C2 C1 C6 C5 57.9(2)
O5 C5 C6 O6 -57.64(19)
C4 C5 C6 O6 -176.93(14)
O5 C5 C6 C1 59.3(2)
C4 C5 C6 C1 -59.99(19)
C1 O1 C7 O7 3.6(3)
C1 O1 C7 C8 -175.06(19)
C2 N1 C9 O8 -0.1(3)
C2 N1 C9 C10 -179.32(18)
C3 O3 C11 O9 -5.4(3)
C3 O3 C11 C12 173.45(17)
C4 O4 C13 O10 3.6(3)
C4 O4 C13 C14 -174.85(19)
C6 O6 C16 O11 1.1(3)
C6 O6 C16 C17 -177.26(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 62707232
