#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/95/2209586.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2209586
loop_
_publ_author_name
'Mendlik, Matthew T.'
'Coleman, Robert S.'
'Qi, Guizhong'
'Lowary, Todd L.'
'McDonald, Robert'
_publ_section_title
;Methyl
 2,3-amino-3-N,4-O-carbonyl-2,3-N-cyclo-2,3,6-trideoxy-β-<small>L</small>-allopyranoside
;
_journal_coeditor_code           LH2066
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2573
_journal_page_last               o2575
_journal_paper_doi               10.1107/S1600536806016709
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C8 H11 N O4'
_chemical_formula_moiety         'C8 H11 N O4'
_chemical_formula_sum            'C8 H11 N O4'
_chemical_formula_weight         185.18
_chemical_melting_point          416
_chemical_name_systematic
;
methyl
2,3-amino-3-N,4-O-carbonyl-2,3-N-cyclo-2,3,6-trideoxy-α-L-allopyranoside
;
_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                   5.7376(6)
_cell_length_b                   9.3890(9)
_cell_length_c                   16.2562(16)
_cell_measurement_reflns_used    6292
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      2.17
_cell_volume                     875.73(15)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2003)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
'Bruker SMART 1000 CCD area detector/PLATFORM'
_diffrn_measurement_method       ω
_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  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6970
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         2.51
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.9722
_exptl_absorpt_correction_T_min  0.7459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1076
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0294
_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)+(0.0517P)²+0.1153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0823
_reflns_number_gt                1014
_reflns_number_total             1076
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2066.cif
_cod_data_source_block           I
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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_database_code               2209586
_cod_database_fobs_code          2209586
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.4202(2) 0.08677(12) 0.37044(7) 0.0345(3) Uani d . 1
O O2 0.3579(3) -0.10326(15) 0.27907(8) 0.0459(4) Uani d . 1
O O3 0.2786(2) 0.11112(12) 0.52861(7) 0.0380(3) Uani d . 1
O O4 0.5914(3) -0.01120(15) 0.57114(9) 0.0486(4) Uani d . 1
N N 0.2850(3) -0.12917(14) 0.50668(9) 0.0376(4) Uani d . 1
C C1 0.4269(3) -0.06206(19) 0.35832(10) 0.0354(4) Uani d . 1
H H1 0.5905 -0.0952 0.3673 0.042 Uiso calc R 1
C C2 0.2702(3) -0.14453(18) 0.41484(11) 0.0376(4) Uani d . 1
H H2 0.2305 -0.2426 0.3953 0.045 Uiso calc R 1
C C3 0.0829(3) -0.07273(18) 0.46091(11) 0.0389(4) Uani d . 1
H H3 -0.0731 -0.1192 0.4666 0.047 Uiso calc R 1
C C4 0.1032(3) 0.08819(18) 0.46511(11) 0.0369(4) Uani d . 1
H H4 -0.0488 0.1328 0.4807 0.044 Uiso calc R 1
C C5 0.1963(3) 0.15052(17) 0.38601(10) 0.0370(4) Uani d . 1
H H5 0.2235 0.2543 0.3960 0.044 Uiso calc R 1
C C6 0.0244(4) 0.1390(2) 0.31579(13) 0.0516(5) Uani d . 1
H H6A 0.0913 0.1825 0.2664 0.062 Uiso calc R 1
H H6B -0.1200 0.1886 0.3305 0.062 Uiso calc R 1
H H6C -0.0096 0.0384 0.3050 0.062 Uiso calc R 1
C C7 0.5067(5) -0.0484(3) 0.21614(12) 0.0619(6) Uani d . 1
H H7A 0.4505 -0.0802 0.1623 0.074 Uiso calc R 1
H H7B 0.6658 -0.0831 0.2248 0.074 Uiso calc R 1
H H7C 0.5057 0.0560 0.2182 0.074 Uiso calc R 1
C C8 0.4068(3) -0.00846(17) 0.53677(10) 0.0350(4) Uani d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0334(6) 0.0337(6) 0.0364(6) -0.0084(5) 0.0051(5) -0.0046(5)
O2 0.0461(8) 0.0517(7) 0.0401(6) 0.0014(7) -0.0059(6) -0.0165(6)
O3 0.0529(8) 0.0250(5) 0.0361(5) 0.0038(6) 0.0093(6) -0.0017(4)
O4 0.0505(8) 0.0463(7) 0.0491(7) 0.0012(7) -0.0089(7) -0.0052(6)
N 0.0429(8) 0.0247(6) 0.0453(7) -0.0006(7) -0.0011(7) 0.0038(6)
C1 0.0323(9) 0.0359(8) 0.0379(8) 0.0041(7) -0.0028(8) -0.0117(7)
C2 0.0438(10) 0.0228(7) 0.0462(9) -0.0010(7) -0.0095(8) -0.0029(6)
C3 0.0308(8) 0.0331(8) 0.0528(9) -0.0046(8) 0.0017(8) 0.0099(8)
C4 0.0347(9) 0.0296(8) 0.0465(9) 0.0078(8) 0.0095(8) 0.0052(7)
C5 0.0453(9) 0.0238(7) 0.0419(9) 0.0020(8) 0.0048(8) 0.0047(7)
C6 0.0509(11) 0.0482(10) 0.0557(11) 0.0113(10) -0.0085(10) 0.0063(10)
C7 0.0628(14) 0.0868(16) 0.0362(9) 0.0043(13) 0.0027(9) -0.0182(11)
C8 0.0425(9) 0.0283(8) 0.0340(7) 0.0009(8) 0.0054(8) -0.0003(6)
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
_geom_angle_publ_flag
C1 O1 C5 117.39(14) yes
C1 O2 C7 112.94(16) yes
C4 O3 C8 108.86(12) yes
C2 N C3 59.27(12) yes
C2 N C8 116.57(14) yes
C3 N C8 105.90(13) yes
O1 C1 O2 113.19(15) yes
O1 C1 C2 114.15(14) yes
O1 C1 H1 108.2 no
O2 C1 C2 104.54(14) yes
O2 C1 H1 108.2 no
C2 C1 H1 108.2 no
N C2 C1 121.67(15) yes
N C2 C3 59.47(11) yes
N C2 H2 114.6 no
C1 C2 C3 120.81(15) yes
C1 C2 H2 114.6 no
C3 C2 H2 114.6 no
N C3 C2 61.25(12) yes
N C3 C4 105.93(15) yes
N C3 H3 120.0 no
C2 C3 C4 115.00(15) yes
C2 C3 H3 120.0 no
C4 C3 H3 120.0 no
O3 C4 C3 103.42(14) yes
O3 C4 C5 107.56(15) yes
O3 C4 H4 111.2 no
C3 C4 C5 112.02(15) yes
C3 C4 H4 111.2 no
C5 C4 H4 111.2 no
O1 C5 C4 107.71(13) yes
O1 C5 C6 114.80(14) yes
O1 C5 H5 107.1 no
C4 C5 C6 112.59(16) yes
C4 C5 H5 107.1 no
C6 C5 H5 107.1 no
C5 C6 H6A 109.5 no
C5 C6 H6B 109.5 no
C5 C6 H6C 109.5 no
H6A C6 H6B 109.5 no
H6A C6 H6C 109.5 no
H6B C6 H6C 109.5 no
O2 C7 H7A 109.5 no
O2 C7 H7B 109.5 no
O2 C7 H7C 109.5 no
H7A C7 H7B 109.5 no
H7A C7 H7C 109.5 no
H7B C7 H7C 109.5 no
O3 C8 O4 123.09(16) yes
O3 C8 N 111.25(15) yes
O4 C8 N 125.41(16) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.412(2) yes
O1 C5 1.440(2) yes
O2 C1 1.4020(19) yes
O2 C7 1.429(3) yes
O3 C4 1.458(2) yes
O3 C8 1.349(2) yes
O4 C8 1.198(3) yes
N C2 1.502(2) yes
N C3 1.476(2) yes
N C8 1.419(2) yes
C1 C2 1.501(3) yes
C1 H1 1.0000 no
C2 C3 1.473(3) yes
C2 H2 1.0000 no
C3 C4 1.517(2) yes
C3 H3 1.0000 no
C4 C5 1.510(2) yes
C4 H4 1.0000 no
C5 C6 1.513(3) yes
C5 H5 1.0000 no
C6 H6A 0.9800 no
C6 H6B 0.9800 no
C6 H6C 0.9800 no
C7 H7A 0.9800 no
C7 H7B 0.9800 no
C7 H7C 0.9800 no
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
_geom_torsion_publ_flag
C5 O1 C1 O2 78.93(18) no
C5 O1 C1 C2 -40.5(2) no
C1 O1 C5 C4 62.15(17) no
C1 O1 C5 C6 -64.13(19) no
C7 O2 C1 O1 62.2(2) no
C7 O2 C1 C2 -172.97(17) no
C8 O3 C4 C3 21.27(17) no
C8 O3 C4 C5 -97.39(15) no
C4 O3 C8 O4 163.76(16) no
C4 O3 C8 N -21.69(18) no
C3 N C2 C1 109.56(19) no
C8 N C2 C1 16.2(2) no
C8 N C2 C3 -93.39(16) no
C2 N C3 C4 -110.16(16) no
C8 N C3 C2 111.82(15) no
C8 N C3 C4 1.66(18) no
C2 N C8 O3 75.34(19) no
C2 N C8 O4 -110.3(2) no
C3 N C8 O3 12.18(18) no
C3 N C8 O4 -173.41(16) no
O1 C1 C2 N -54.9(2) no
O1 C1 C2 C3 16.1(2) no
O2 C1 C2 N -179.07(15) no
O2 C1 C2 C3 -108.15(17) no
N C2 C3 C4 95.15(17) no
C1 C2 C3 N -110.98(17) no
C1 C2 C3 C4 -15.8(2) no
N C3 C4 O3 -13.38(18) no
N C3 C4 C5 102.15(17) no
C2 C3 C4 O3 -78.62(17) no
C2 C3 C4 C5 36.9(2) no
O3 C4 C5 O1 54.93(16) no
O3 C4 C5 C6 -177.49(13) no
C3 C4 C5 O1 -58.0(2) no
C3 C4 C5 C6 69.5(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10148599
