#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/65/1506568.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_1506568
loop_
_publ_author_name
'Wang, Ruo-Wen'
'Qing, Feng-Ling'
_publ_section_title
;
 Highly stereocontrolled synthesis of gem-difluoromethylenated azasugars:
 D- and L-1,4,6-trideoxy-4,4-difluoronojirimycin.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2189
_journal_page_last               2192
_journal_paper_doi               10.1021/ol050558h
_journal_volume                  7
_journal_year                    2005
_chemical_absolute_configuration ad
_chemical_formula_sum            'C6 H11 F2 N O2'
_chemical_formula_weight         167.16
_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            8
_cell_length_a                   9.6285(9)
_cell_length_b                   10.2351(9)
_cell_length_c                   15.0732(13)
_cell_measurement_reflns_used    4487
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55.091
_cell_measurement_theta_min      4.811
_cell_volume                     1485.4(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0880
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8702
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72331
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.511
_exptl_crystal_size_mid          0.488
_exptl_crystal_size_min          0.257
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.1(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         3231
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0413
_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)+(0.0527P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.0994
_reflns_number_gt                2998
_reflns_number_total             3231
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol050558hsi20050314_115827.cif
_cod_data_source_block           cd24522
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1506568
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
F1 F 1.07743(13) 0.19193(13) 0.21590(7) 0.0457(3) Uani 1 1 d .
F2 F 1.12445(15) 0.00835(12) 0.28341(10) 0.0583(4) Uani 1 1 d .
F3 F 0.98389(11) 0.35584(12) 1.03253(7) 0.0390(3) Uani 1 1 d .
F4 F 0.77601(12) 0.41949(12) 0.99593(9) 0.0451(3) Uani 1 1 d .
N1 N 1.03172(17) 0.31942(15) 0.38635(10) 0.0332(3) Uani 1 1 d .
N2 N 1.02820(16) 0.25109(15) 0.85959(9) 0.0296(3) Uani 1 1 d D
O1 O 0.67488(15) 0.20412(15) 0.32415(10) 0.0409(3) Uani 1 1 d D
O2 O 0.84917(17) 0.02485(13) 0.22614(9) 0.0417(3) Uani 1 1 d D
O3 O 0.87126(15) -0.03631(13) 0.96842(9) 0.0395(3) Uani 1 1 d D
O4 O 0.78682(14) 0.17688(15) 1.08272(9) 0.0379(3) Uani 1 1 d D
C1 C 0.8829(2) 0.29580(19) 0.39377(12) 0.0384(4) Uani 1 1 d .
C2 C 0.8199(2) 0.22372(16) 0.31440(11) 0.0299(4) Uani 1 1 d .
C3 C 0.8980(2) 0.09586(16) 0.29989(11) 0.0316(4) Uani 1 1 d .
C4 C 1.0526(2) 0.12329(17) 0.29338(12) 0.0335(4) Uani 1 1 d .
C5 C 1.1121(2) 0.19996(18) 0.37134(12) 0.0337(4) Uani 1 1 d .
C6 C 1.2652(3) 0.2311(3) 0.35895(16) 0.0483(5) Uani 1 1 d .
C7 C 0.9749(2) 0.11739(18) 0.86974(11) 0.0324(4) Uani 1 1 d .
C8 C 0.92922(19) 0.09165(16) 0.96494(11) 0.0278(3) Uani 1 1 d .
C9 C 0.82171(17) 0.19321(17) 0.99293(11) 0.0274(4) Uani 1 1 d .
C10 C 0.87695(17) 0.32959(17) 0.97546(11) 0.0280(3) Uani 1 1 d .
C11 C 0.92411(19) 0.35126(19) 0.88009(12) 0.0326(4) Uani 1 1 d .
C12 C 0.9847(3) 0.4869(2) 0.86615(19) 0.0528(6) Uani 1 1 d .
H1 H 0.836(3) 0.377(3) 0.4020(15) 0.045(6) Uiso 1 1 d .
H2 H 0.863(2) 0.249(2) 0.4496(16) 0.050(7) Uiso 1 1 d .
H3 H 0.832(2) 0.283(2) 0.2621(12) 0.024(5) Uiso 1 1 d .
H4 H 0.8863(19) 0.042(2) 0.3505(13) 0.028(5) Uiso 1 1 d .
H5 H 1.0983(18) 0.144(2) 0.4228(13) 0.028(5) Uiso 1 1 d .
H6 H 1.279(3) 0.295(3) 0.3089(17) 0.057(7) Uiso 1 1 d .
H7 H 1.325(3) 0.157(4) 0.348(2) 0.078(10) Uiso 1 1 d .
H8 H 1.306(3) 0.273(3) 0.412(2) 0.078(10) Uiso 1 1 d .
H9 H 1.051(2) 0.373(2) 0.3413(14) 0.031(5) Uiso 1 1 d .
H10 H 0.667(3) 0.154(3) 0.3689(16) 0.070(9) Uiso 1 1 d D
H11 H 0.844(4) 0.084(3) 0.1836(19) 0.102(13) Uiso 1 1 d D
H12 H 1.052(2) 0.057(3) 0.8578(14) 0.042(6) Uiso 1 1 d .
H13 H 0.893(2) 0.100(2) 0.8311(15) 0.038(6) Uiso 1 1 d .
H14 H 1.010(2) 0.101(2) 1.0017(14) 0.031(5) Uiso 1 1 d .
H15 H 0.736(2) 0.184(2) 0.9566(13) 0.036(5) Uiso 1 1 d .
H16 H 0.840(2) 0.338(2) 0.8454(13) 0.032(5) Uiso 1 1 d .
H17 H 0.914(3) 0.553(3) 0.875(2) 0.077(9) Uiso 1 1 d .
H18 H 1.067(4) 0.500(3) 0.902(2) 0.095(12) Uiso 1 1 d .
H19 H 1.022(3) 0.494(3) 0.809(2) 0.091(11) Uiso 1 1 d .
H20 H 1.056(2) 0.268(2) 0.8074(11) 0.038(6) Uiso 1 1 d D
H21 H 0.901(3) -0.071(3) 1.0170(13) 0.059(8) Uiso 1 1 d D
H22 H 0.7041(18) 0.203(2) 1.0858(14) 0.039(6) Uiso 1 1 d 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'
F F 0.0171 0.0103 '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 N1 C5 113.14(15)
C1 N1 H9 111.2(13)
C5 N1 H9 106.9(14)
C11 N2 C7 112.99(14)
C11 N2 H20 105.7(16)
C7 N2 H20 113.3(16)
C2 O1 H10 105(2)
C3 O2 H11 104(2)
C8 O3 H21 106.0(19)
C9 O4 H22 104.0(15)
N1 C1 C2 114.15(15)
N1 C1 H1 109.4(15)
C2 C1 H1 109.5(15)
N1 C1 H2 109.8(14)
C2 C1 H2 110.9(14)
H1 C1 H2 102.4(19)
O1 C2 C3 112.26(15)
O1 C2 C1 112.14(15)
C3 C2 C1 109.30(15)
O1 C2 H3 106.3(11)
C3 C2 H3 110.3(11)
C1 C2 H3 106.3(11)
O2 C3 C4 111.81(15)
O2 C3 C2 113.04(15)
C4 C3 C2 109.51(14)
O2 C3 H4 107.2(13)
C4 C3 H4 106.0(12)
C2 C3 H4 109.0(13)
F2 C4 F1 104.81(15)
F2 C4 C3 110.04(15)
F1 C4 C3 108.54(15)
F2 C4 C5 109.63(15)
F1 C4 C5 108.92(15)
C3 C4 C5 114.44(15)
N1 C5 C6 110.87(17)
N1 C5 C4 110.49(14)
C6 C5 C4 112.20(17)
N1 C5 H5 107.1(12)
C6 C5 H5 110.8(11)
C4 C5 H5 105.2(12)
C5 C6 H6 111.0(16)
C5 C6 H7 116(2)
H6 C6 H7 107(2)
C5 C6 H8 111.9(18)
H6 C6 H8 106(2)
H7 C6 H8 104(3)
N2 C7 C8 111.09(14)
N2 C7 H12 107.8(14)
C8 C7 H12 106.3(13)
N2 C7 H13 112.3(14)
C8 C7 H13 107.0(13)
H12 C7 H13 112.2(18)
O3 C8 C7 107.86(14)
O3 C8 C9 110.50(15)
C7 C8 C9 109.78(14)
O3 C8 H14 112.8(12)
C7 C8 H14 107.0(13)
C9 C8 H14 108.8(12)
O4 C9 C10 111.14(15)
O4 C9 C8 110.34(14)
C10 C9 C8 109.93(14)
O4 C9 H15 108.8(12)
C10 C9 H15 106.4(13)
C8 C9 H15 110.1(13)
F3 C10 F4 105.05(14)
F3 C10 C9 109.60(14)
F4 C10 C9 109.23(14)
F3 C10 C11 109.89(14)
F4 C10 C11 108.98(14)
C9 C10 C11 113.71(14)
N2 C11 C12 110.32(16)
N2 C11 C10 107.50(14)
C12 C11 C10 112.18(18)
N2 C11 H16 110.9(12)
C12 C11 H16 111.8(13)
C10 C11 H16 103.9(12)
C11 C12 H17 110(2)
C11 C12 H18 111(2)
H17 C12 H18 114(3)
C11 C12 H19 110(2)
H17 C12 H19 110(3)
H18 C12 H19 101(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C4 1.384(2)
F2 C4 1.373(2)
F3 C10 1.368(2)
F4 C10 1.373(2)
N1 C1 1.458(3)
N1 C5 1.465(2)
N1 H9 0.89(2)
N2 C11 1.467(2)
N2 C7 1.469(2)
N2 H20 0.850(16)
O1 C2 1.419(2)
O1 H10 0.852(17)
O2 C3 1.409(2)
O2 H11 0.884(19)
O3 C8 1.425(2)
O3 H21 0.861(17)
O4 C9 1.404(2)
O4 H22 0.842(16)
C1 C2 1.531(3)
C1 H1 0.95(3)
C1 H2 0.99(2)
C2 C3 1.525(2)
C2 H3 0.998(19)
C3 C4 1.518(3)
C3 H4 0.95(2)
C4 C5 1.525(2)
C5 C6 1.520(3)
C5 H5 0.97(2)
C6 H6 1.01(3)
C6 H7 0.97(3)
C6 H8 0.99(3)
C7 C8 1.524(2)
C7 H12 0.98(2)
C7 H13 0.99(2)
C8 C9 1.526(2)
C8 H14 0.96(2)
C9 C10 1.517(2)
C9 H15 0.99(2)
C10 C11 1.524(2)
C11 C12 1.521(3)
C11 H16 0.97(2)
C12 H17 0.97(3)
C12 H18 0.97(4)
C12 H19 0.93(4)
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
C5 N1 C1 C2 -55.6(2)
N1 C1 C2 O1 -179.41(15)
N1 C1 C2 C3 55.4(2)
O1 C2 C3 O2 56.7(2)
C1 C2 C3 O2 -178.24(15)
O1 C2 C3 C4 -177.95(14)
C1 C2 C3 C4 -52.86(19)
O2 C3 C4 F2 -56.01(19)
C2 C3 C4 F2 177.91(14)
O2 C3 C4 F1 58.15(18)
C2 C3 C4 F1 -67.93(18)
O2 C3 C4 C5 -179.98(14)
C2 C3 C4 C5 53.9(2)
C1 N1 C5 C6 176.80(15)
C1 N1 C5 C4 51.8(2)
F2 C4 C5 N1 -176.72(14)
F1 C4 C5 N1 69.13(19)
C3 C4 C5 N1 -52.5(2)
F2 C4 C5 C6 59.0(2)
F1 C4 C5 C6 -55.2(2)
C3 C4 C5 C6 -176.82(16)
C11 N2 C7 C8 -61.07(19)
N2 C7 C8 O3 176.50(14)
N2 C7 C8 C9 56.04(19)
O3 C8 C9 O4 65.78(18)
C7 C8 C9 O4 -175.37(14)
O3 C8 C9 C10 -171.30(14)
C7 C8 C9 C10 -52.45(18)
O4 C9 C10 F3 53.44(17)
C8 C9 C10 F3 -69.01(16)
O4 C9 C10 F4 -61.15(17)
C8 C9 C10 F4 176.39(13)
O4 C9 C10 C11 176.87(14)
C8 C9 C10 C11 54.42(18)
C7 N2 C11 C12 -178.62(17)
C7 N2 C11 C10 58.77(18)
F3 C10 C11 N2 67.25(18)
F4 C10 C11 N2 -178.13(14)
C9 C10 C11 N2 -56.02(18)
F3 C10 C11 C12 -54.2(2)
F4 C10 C11 C12 60.4(2)
C9 C10 C11 C12 -177.46(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 23269765
