#------------------------------------------------------------------------------
#$Date: 2019-11-26 14:18:37 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243491 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/61/1556130.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_1556130
loop_
_publ_author_name
'Lumbroso, Alexandre'
'Beaudet, Isabelle'
'Toupet, Loïc'
'Le Grognec, Erwan'
'Quintard, Jean-Paul'
_publ_section_title
;
 Stereodivergent synthesis of iminosugars from stannylated derivatives of
 (S)-vinylglycinol.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              160
_journal_page_last               163
_journal_paper_doi               10.1021/ol303213r
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C13 H19 N O3'
_chemical_formula_weight         237.29
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_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                   9.9170(10)
_cell_length_b                   10.626(2)
_cell_length_c                   11.3360(10)
_cell_measurement_temperature    150(2)
_cell_volume                     1194.6(3)
_computing_cell_refinement
'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.26'
_computing_data_collection
'CrysAlis CCD, Oxford Diffraction Ltd.,Version 1.171.26'
_computing_data_reduction
'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.26'
_computing_molecular_graphics    'PLATON_(Spek, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97_(Altomare & al., 1998)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 19.64
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD Saphire 3 Xcalibur'
_diffrn_measurement_method       'omega 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  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0156
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_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            14755
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.033
_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   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2595
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0282
_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)+(0.0576P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0820
_reflns_number_gt                2351
_reflns_number_total             2595
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol303213r_si_003.cif
_cod_data_source_block           elg6
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1556130
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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 -0.08299(9) 0.98848(9) 0.34849(8) 0.0315(2) Uani 1 1 d .
O2 O -0.22227(9) 1.05718(9) 0.20751(8) 0.0284(2) Uani 1 1 d .
O3 O 0.17471(10) 0.91042(9) 0.36123(7) 0.0294(2) Uani 1 1 d .
H3 H 0.1002 0.9393 0.3838 0.044 Uiso 1 1 calc R
N1 N -0.00438(10) 1.03587(9) 0.15984(8) 0.0187(2) Uani 1 1 d .
C1 C -0.09873(12) 1.02224(11) 0.24664(10) 0.0226(3) Uani 1 1 d .
C2 C -0.20948(14) 1.10192(13) 0.08640(11) 0.0268(3) Uani 1 1 d .
H2A H -0.2080 1.1950 0.0834 0.032 Uiso 1 1 calc R
H2B H -0.2846 1.0707 0.0369 0.032 Uiso 1 1 calc R
C3 C -0.07475(12) 1.04687(11) 0.04598(10) 0.0216(2) Uani 1 1 d .
H3A H -0.0266 1.1071 -0.0072 0.026 Uiso 1 1 calc R
C4 C -0.08630(13) 0.91904(12) -0.01118(10) 0.0250(3) Uani 1 1 d .
H4 H -0.1446 0.9094 -0.0770 0.030 Uiso 1 1 calc R
C5 C -0.01830(14) 0.81983(12) 0.02689(11) 0.0259(3) Uani 1 1 d .
H5 H -0.0351 0.7410 -0.0097 0.031 Uiso 1 1 calc R
C6 C 0.08442(13) 0.82466(11) 0.12519(11) 0.0247(3) Uani 1 1 d .
H6A H 0.1663 0.7778 0.1013 0.030 Uiso 1 1 calc R
H6B H 0.0469 0.7837 0.1965 0.030 Uiso 1 1 calc R
C7 C 0.12222(12) 0.96111(10) 0.15396(10) 0.0178(2) Uani 1 1 d .
H7 H 0.1719 0.9930 0.0833 0.021 Uiso 1 1 calc R
C8 C 0.21955(12) 0.97868(11) 0.25943(10) 0.0201(2) Uani 1 1 d .
C9 C 0.35867(12) 0.92309(11) 0.23056(11) 0.0218(3) Uani 1 1 d .
H9A H 0.4143 0.9234 0.3031 0.026 Uiso 1 1 calc R
H9B H 0.3471 0.8344 0.2058 0.026 Uiso 1 1 calc R
C10 C 0.43404(12) 0.99390(11) 0.13380(11) 0.0230(3) Uani 1 1 d .
H10A H 0.3862 0.9826 0.0579 0.028 Uiso 1 1 calc R
H10B H 0.5257 0.9581 0.1253 0.028 Uiso 1 1 calc R
C11 C 0.44483(14) 1.13443(11) 0.16161(13) 0.0291(3) Uani 1 1 d .
H11A H 0.4842 1.1787 0.0929 0.035 Uiso 1 1 calc R
H11B H 0.5063 1.1465 0.2295 0.035 Uiso 1 1 calc R
C12 C 0.30714(14) 1.19225(11) 0.19069(12) 0.0286(3) Uani 1 1 d .
H12A H 0.3194 1.2809 0.2155 0.034 Uiso 1 1 calc R
H12B H 0.2498 1.1916 0.1192 0.034 Uiso 1 1 calc R
C13 C 0.23682(13) 1.11897(11) 0.28927(11) 0.0253(3) Uani 1 1 d .
H13A H 0.1470 1.1565 0.3039 0.030 Uiso 1 1 calc R
H13B H 0.2902 1.1269 0.3627 0.030 Uiso 1 1 calc R
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
C1 O2 C2 108.60(9)
C8 O3 H3 109.5
C1 N1 C3 108.38(9)
C1 N1 C7 123.65(10)
C3 N1 C7 113.79(9)
O1 C1 O2 120.44(11)
O1 C1 N1 128.75(12)
O2 C1 N1 110.77(10)
O2 C2 C3 103.50(10)
O2 C2 H2A 111.1
C3 C2 H2A 111.1
O2 C2 H2B 111.1
C3 C2 H2B 111.1
H2A C2 H2B 109.0
N1 C3 C4 109.93(10)
N1 C3 C2 100.48(9)
C4 C3 C2 114.00(10)
N1 C3 H3A 110.7
C4 C3 H3A 110.7
C2 C3 H3A 110.7
C5 C4 C3 122.56(11)
C5 C4 H4 118.7
C3 C4 H4 118.7
C4 C5 C6 123.84(11)
C4 C5 H5 118.1
C6 C5 H5 118.1
C5 C6 C7 110.73(10)
C5 C6 H6A 109.5
C7 C6 H6A 109.5
C5 C6 H6B 109.5
C7 C6 H6B 109.5
H6A C6 H6B 108.1
N1 C7 C6 107.96(10)
N1 C7 C8 115.30(9)
C6 C7 C8 115.52(9)
N1 C7 H7 105.7
C6 C7 H7 105.7
C8 C7 H7 105.7
O3 C8 C9 104.80(9)
O3 C8 C13 110.35(9)
C9 C8 C13 108.64(10)
O3 C8 C7 111.55(10)
C9 C8 C7 110.44(9)
C13 C8 C7 110.86(9)
C10 C9 C8 113.80(9)
C10 C9 H9A 108.8
C8 C9 H9A 108.8
C10 C9 H9B 108.8
C8 C9 H9B 108.8
H9A C9 H9B 107.7
C9 C10 C11 111.56(10)
C9 C10 H10A 109.3
C11 C10 H10A 109.3
C9 C10 H10B 109.3
C11 C10 H10B 109.3
H10A C10 H10B 108.0
C10 C11 C12 111.91(10)
C10 C11 H11A 109.2
C12 C11 H11A 109.2
C10 C11 H11B 109.2
C12 C11 H11B 109.2
H11A C11 H11B 107.9
C13 C12 C11 111.04(11)
C13 C12 H12A 109.4
C11 C12 H12A 109.4
C13 C12 H12B 109.4
C11 C12 H12B 109.4
H12A C12 H12B 108.0
C12 C13 C8 112.54(10)
C12 C13 H13A 109.1
C8 C13 H13A 109.1
C12 C13 H13B 109.1
C8 C13 H13B 109.1
H13A C13 H13B 107.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2191(15)
O2 C1 1.3548(15)
O2 C2 1.4585(16)
O3 C8 1.4337(13)
O3 H3 0.8400
N1 C1 1.3655(15)
N1 C3 1.4720(14)
N1 C7 1.4871(15)
C2 C3 1.5288(18)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.5093(17)
C3 H3A 1.0000
C4 C5 1.3238(19)
C4 H4 0.9500
C5 C6 1.5107(17)
C5 H5 0.9500
C6 C7 1.5327(16)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.5479(16)
C7 H7 1.0000
C8 C9 1.5360(17)
C8 C13 1.5382(16)
C9 C10 1.5257(16)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.5300(17)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.5332(19)
C11 H11A 0.9900
C11 H11B 0.9900
C12 C13 1.5302(19)
C12 H12A 0.9900
C12 H12B 0.9900
C13 H13A 0.9900
C13 H13B 0.9900
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
C2 O2 C1 O1 175.62(11)
C2 O2 C1 N1 -2.11(13)
C3 N1 C1 O1 165.71(13)
C7 N1 C1 O1 28.67(19)
C3 N1 C1 O2 -16.79(13)
C7 N1 C1 O2 -153.83(10)
C1 O2 C2 C3 18.99(12)
C1 N1 C3 C4 -93.49(11)
C7 N1 C3 C4 48.20(12)
C1 N1 C3 C2 26.98(12)
C7 N1 C3 C2 168.67(9)
O2 C2 C3 N1 -26.92(11)
O2 C2 C3 C4 90.59(12)
N1 C3 C4 C5 -12.33(17)
C2 C3 C4 C5 -124.25(13)
C3 C4 C5 C6 -4.3(2)
C4 C5 C6 C7 -13.09(17)
C1 N1 C7 C6 68.86(13)
C3 N1 C7 C6 -66.17(12)
C1 N1 C7 C8 -62.00(14)
C3 N1 C7 C8 162.97(9)
C5 C6 C7 N1 45.17(12)
C5 C6 C7 C8 175.91(10)
N1 C7 C8 O3 77.31(12)
C6 C7 C8 O3 -49.83(14)
N1 C7 C8 C9 -166.56(9)
C6 C7 C8 C9 66.30(13)
N1 C7 C8 C13 -46.10(13)
C6 C7 C8 C13 -173.24(10)
O3 C8 C9 C10 -172.47(9)
C13 C8 C9 C10 -54.52(12)
C7 C8 C9 C10 67.27(12)
C8 C9 C10 C11 53.63(13)
C9 C10 C11 C12 -52.08(14)
C10 C11 C12 C13 53.76(14)
C11 C12 C13 C8 -56.64(14)
O3 C8 C13 C12 170.19(10)
C9 C8 C13 C12 55.82(13)
C7 C8 C13 C12 -65.71(14)
