#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/60/1506060.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_1506060
loop_
_publ_author_name
'Alegret, Carlos'
'Benet-Buchholz, Jordi'
'Riera, Antoni'
_publ_contact_author
;
    Dr. Benet-Buchholz, Jordi
    Institut Català d'Investigació Química (ICIQ)    
    X-ray Diffraction Unit
    Avgda. Paīsos Catalans 16
    E-43007 Tarragona, Spain
;
_publ_section_title
;
 Stereodivergent syntheses of conduramines and aminocyclitols.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3069
_journal_page_last               3072
_journal_paper_doi               10.1021/ol061022e
_journal_volume                  8
_journal_year                    2006
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C15 H23 N O6'
_chemical_formula_weight         313.34
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 91.616(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.6041(4)
_cell_length_b                   8.7530(4)
_cell_length_c                   11.3766(5)
_cell_measurement_reflns_used    8991
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      71.68
_cell_measurement_theta_min      3.89
_cell_volume                     856.45(7)
_computing_cell_refinement       'SAINT+ Version 6.22 Bruker AXS, 2002'
_computing_data_collection       'Bruker-Nonius, Proteum 1.37, 2002'
_computing_data_reduction        'SAINT+ Version 6.22 Bruker AXS, 2002'
_computing_molecular_graphics    'Shelxtl Version 6.10 (Sheldrick, 2000)'
_computing_publication_material  'Shelxtl Version 6.10 (Sheldrick, 2000)'
_computing_structure_refinement  'Shelxtl Version 6.10 (Sheldrick, 2000)'
_computing_structure_solution    'Shelxtl Version 6.10 (Sheldrick, 2000)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 1024
_diffrn_detector_type            'Proteum CCD area detector 6000 K'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'three-circle diffractometer bruker-nonius'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support
'magnetic support whith 10 micron nylon fiber cryoloop'
_diffrn_radiation_monochromator  'Multilayer Montel mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_sigmaI/netI    0.0521
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8729
_diffrn_reflns_theta_full        71.67
_diffrn_reflns_theta_max         71.67
_diffrn_reflns_theta_min         3.89
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_source_current           120
_diffrn_source_power             40
_diffrn_source_size              '3 mm x 0.3 mm fine focus'
_diffrn_source_type              'Bruker-Nonius FR 591'
_exptl_absorpt_coefficient_mu    0.785
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6984
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 SADABS Version 2.1 2003 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(13)
_refine_ls_extinction_coef       0.065(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3060
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0413
_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)+(0.0668P)²+0.0533P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.0992
_reflns_number_gt                3037
_reflns_number_total             3060
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol061022esi20060428_063129.cif
_cod_data_source_block           cam12702g
_cod_depositor_comments
;
The following automatic conversions were performed:
'_diffrn_measurement_specimen_suppport' tag replaced with
'_diffrn_measurement_specimen_support'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1506060
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
O1 O -0.08383(14) -0.89847(15) -0.72311(9) 0.0298(3) Uani 1 1 d .
N1 N -0.20431(14) -1.06521(15) -0.60312(10) 0.0174(3) Uani 1 1 d .
H1B H -0.277(3) -1.131(3) -0.6011(18) 0.023(5) Uiso 1 1 d .
C1 C -0.13694(15) -1.00040(16) -0.49609(12) 0.0162(3) Uani 1 1 d .
H1A H -0.0427(19) -0.945(2) -0.5128(15) 0.009(4) Uiso 1 1 d .
O2 O -0.24544(12) -1.08393(13) -0.79556(9) 0.0230(3) Uani 1 1 d .
C2 C -0.23970(16) -0.87936(17) -0.44201(11) 0.0164(3) Uani 1 1 d .
H2A H -0.2805(19) -0.8025(19) -0.5006(14) 0.007(4) Uiso 1 1 d .
O3 O -0.36990(11) -0.95782(12) -0.39082(9) 0.0187(2) Uani 1 1 d .
C3 C -0.14525(17) -0.80035(16) -0.34462(12) 0.0174(3) Uani 1 1 d .
H3A H -0.063(2) -0.735(2) -0.3797(16) 0.017(4) Uiso 1 1 d .
O4 O -0.53090(13) -0.76251(15) -0.43383(10) 0.0273(3) Uani 1 1 d .
C4 C -0.07577(16) -0.91378(19) -0.26023(12) 0.0202(3) Uani 1 1 d .
H4A H -0.045(2) -0.873(3) -0.1865(18) 0.026(5) Uiso 1 1 d .
O5 O -0.24069(12) -0.69641(13) -0.27850(9) 0.0204(2) Uani 1 1 d .
C5 C -0.05515(17) -1.05933(19) -0.28842(12) 0.0202(3) Uani 1 1 d .
H5A H -0.008(2) -1.130(3) -0.2336(19) 0.027(5) Uiso 1 1 d .
O6 O -0.22477(13) -0.52741(13) -0.42669(11) 0.0262(3) Uani 1 1 d .
C6 C -0.09850(17) -1.12515(17) -0.40642(13) 0.0195(3) Uani 1 1 d .
H6A H -0.188(2) -1.202(3) -0.4023(18) 0.024(5) Uiso 1 1 d .
H6B H -0.009(2) -1.189(3) -0.4345(16) 0.025(5) Uiso 1 1 d .
C7 C -0.17100(17) -1.00535(18) -0.70853(13) 0.0188(3) Uani 1 1 d .
C8 C -0.2195(2) -1.0436(2) -0.91887(13) 0.0263(4) Uani 1 1 d .
C9 C -0.0476(2) -1.0565(3) -0.94583(14) 0.0371(5) Uani 1 1 d .
H9A H -0.006(3) -1.149(3) -0.917(2) 0.034(6) Uiso 1 1 d .
H9B H 0.017(4) -0.970(5) -0.907(3) 0.068(9) Uiso 1 1 d .
H9C H -0.043(3) -1.055(3) -1.028(2) 0.041(6) Uiso 1 1 d .
C10 C -0.2814(2) -0.8849(2) -0.94518(14) 0.0320(4) Uani 1 1 d .
H10A H -0.225(3) -0.804(3) -0.902(3) 0.050(7) Uiso 1 1 d .
H10B H -0.395(3) -0.869(4) -0.930(2) 0.055(8) Uiso 1 1 d .
H10C H -0.274(3) -0.863(3) -1.0358(19) 0.032(5) Uiso 1 1 d .
C11 C -0.3134(3) -1.1626(3) -0.98515(18) 0.0497(6) Uani 1 1 d .
H11A H -0.267(3) -1.269(3) -0.965(2) 0.038(6) Uiso 1 1 d .
H11B H -0.301(3) -1.146(4) -1.066(3) 0.054(8) Uiso 1 1 d .
H11C H -0.416(3) -1.153(3) -0.962(2) 0.044(7) Uiso 1 1 d .
C12 C -0.50700(16) -0.8838(2) -0.38855(13) 0.0216(3) Uani 1 1 d .
C13 C -0.62200(18) -0.9742(2) -0.32057(15) 0.0309(4) Uani 1 1 d .
H13A H -0.7253 -0.9280 -0.3304 0.046 Uiso 1 1 calc R
H13B H -0.5908 -0.9741 -0.2371 0.046 Uiso 1 1 calc R
H13C H -0.6251 -1.0795 -0.3498 0.046 Uiso 1 1 calc R
C14 C -0.27119(16) -0.56130(18) -0.33192(14) 0.0219(3) Uani 1 1 d .
C15 C -0.3702(2) -0.4623(2) -0.25689(18) 0.0330(4) Uani 1 1 d .
H15A H -0.395(3) -0.368(3) -0.300(2) 0.037(6) Uiso 1 1 d .
H15B H -0.314(4) -0.428(4) -0.194(3) 0.056(8) Uiso 1 1 d .
H15C H -0.453(4) -0.516(4) -0.235(3) 0.067(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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 N1 C1 120.38(12)
N1 C1 C2 112.90(11)
N1 C1 C6 110.86(12)
C2 C1 C6 110.24(11)
C7 O2 C8 119.69(12)
O3 C2 C1 107.28(11)
O3 C2 C3 109.00(10)
C1 C2 C3 107.85(11)
C12 O3 C2 117.83(12)
O5 C3 C4 107.81(11)
O5 C3 C2 111.37(11)
C4 C3 C2 111.20(12)
C5 C4 C3 122.45(13)
C14 O5 C3 114.91(11)
C4 C5 C6 123.65(14)
C5 C6 C1 111.59(13)
O1 C7 N1 124.72(14)
O1 C7 O2 125.03(13)
N1 C7 O2 110.24(13)
O2 C8 C11 102.59(15)
O2 C8 C10 110.30(13)
C11 C8 C10 110.74(17)
O2 C8 C9 110.42(13)
C11 C8 C9 110.96(18)
C10 C8 C9 111.50(15)
O4 C12 O3 124.00(14)
O4 C12 C13 125.67(14)
O3 C12 C13 110.32(14)
O6 C14 O5 123.78(14)
O6 C14 C15 125.36(15)
O5 C14 C15 110.86(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.213(2)
N1 C7 1.347(2)
N1 C1 1.4494(17)
C1 C2 1.5209(19)
C1 C6 1.524(2)
O2 C7 1.3519(19)
O2 C8 1.4697(18)
C2 O3 1.4500(16)
C2 C3 1.5217(19)
O3 C12 1.3467(19)
C3 O5 1.4500(17)
C3 C4 1.494(2)
O4 C12 1.195(2)
C4 C5 1.327(2)
O5 C14 1.352(2)
C5 C6 1.498(2)
O6 C14 1.198(2)
C8 C11 1.507(3)
C8 C10 1.514(3)
C8 C9 1.523(3)
C12 C13 1.499(2)
C14 C15 1.499(2)
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 N1 C1 C2 92.39(15)
C7 N1 C1 C6 -143.36(14)
N1 C1 C2 O3 72.89(14)
C6 C1 C2 O3 -51.70(14)
N1 C1 C2 C3 -169.82(11)
C6 C1 C2 C3 65.58(14)
C1 C2 O3 C12 -148.98(12)
C3 C2 O3 C12 94.49(14)
O3 C2 C3 O5 -56.58(15)
C1 C2 C3 O5 -172.74(11)
O3 C2 C3 C4 63.68(14)
C1 C2 C3 C4 -52.48(14)
O5 C3 C4 C5 143.43(14)
C2 C3 C4 C5 21.09(19)
C4 C3 O5 C14 159.79(12)
C2 C3 O5 C14 -77.96(15)
C3 C4 C5 C6 0.1(2)
C4 C5 C6 C1 11.7(2)
N1 C1 C6 C5 -170.03(11)
C2 C1 C6 C5 -44.27(16)
C1 N1 C7 O1 1.2(2)
C1 N1 C7 O2 179.64(11)
C8 O2 C7 O1 1.7(2)
C8 O2 C7 N1 -176.78(13)
C7 O2 C8 C11 176.41(17)
C7 O2 C8 C10 -65.59(18)
C7 O2 C8 C9 58.1(2)
C2 O3 C12 O4 5.8(2)
C2 O3 C12 C13 -173.46(12)
C3 O5 C14 O6 0.2(2)
C3 O5 C14 C15 -179.99(13)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21199780 ChemSpider
2 139039418 PubChem
