#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/61/2016158.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_2016158
loop_
_publ_author_name
'Rodríguez, Ricaurte'
'Cobo, Justo'
'Nogueras, Manuel'
'Low, John N.'
'Glidewell, Christopher'
_publ_section_title
;
 Hydrogen-bonded sheets of R₂²(10) and R₄⁴(24)
 rings in 1-deoxy-1-morpholino-<small>D</small>-fructopyranose
;
_journal_coeditor_code           GG3112
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o507
_journal_page_last               o509
_journal_paper_doi               10.1107/S0108270107034312
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C10 H19 N O6'
_chemical_formula_moiety         'C10 H19 N O6'
_chemical_formula_sum            'C10 H19 N O6'
_chemical_formula_weight         249.26
_chemical_melting_point          420
_chemical_name_systematic
;
1-deoxy-1-morpholino-D-fructopyranose
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                104.598(10)
_cell_angle_beta                 90.393(12)
_cell_angle_gamma                104.834(10)
_cell_formula_units_Z            1
_cell_length_a                   5.2767(8)
_cell_length_b                   5.5375(5)
_cell_length_c                   10.2809(13)
_cell_measurement_reflns_used    1279
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.94
_cell_volume                     280.20(6)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg et al.,  2000)'
_computing_data_collection       'COLLECT (Hooft, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg et al.,  2003)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement
'OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'Sir2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7471
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.94
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             134
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.228
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1279
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0351P)²+0.0939P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0749
_reflns_number_gt                1163
_reflns_number_total             1279
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg3112.cif
_cod_data_source_block           I
_cod_original_cell_volume        280.19(6)
_cod_database_code               2016158
_cod_database_fobs_code          2016158
loop_
_symmetry_equiv_pos_as_xyz
'x, y, 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
C C1 0.8058(4) 0.5379(4) 0.4170(2) 0.0129(4) Uani d . 1
O O1 0.6404(3) 0.4344(3) 0.61585(15) 0.0123(3) Uani d . 1
O O2 0.4747(3) 0.7179(3) 0.52752(17) 0.0143(3) Uani d . 1
O O3 0.9703(3) 1.0861(3) 0.58303(16) 0.0160(4) Uani d . 1
O O4 0.9784(3) 1.1528(3) 0.87384(17) 0.0170(4) Uani d . 1
O O5 0.9330(3) 0.6445(3) 0.87697(18) 0.0175(4) Uani d . 1
O O11 0.3306(3) -0.0073(3) 0.08231(17) 0.0177(4) Uani d . 1
N N14 0.5902(4) 0.3908(4) 0.31449(19) 0.0133(4) Uani d . 1
C C2 0.7003(4) 0.6418(4) 0.5512(2) 0.0116(5) Uani d . 1
C C3 0.9004(5) 0.8760(4) 0.6437(2) 0.0122(4) Uani d . 1
C C4 0.7911(4) 0.9523(4) 0.7804(2) 0.0128(5) Uani d . 1
C C5 0.7099(5) 0.7228(4) 0.8417(2) 0.0141(5) Uani d . 1
C C6 0.5232(4) 0.4989(4) 0.7411(2) 0.0137(5) Uani d . 1
C C12 0.2641(5) -0.0188(5) 0.2152(2) 0.0175(5) Uani d . 1
C C13 0.4932(5) 0.1186(4) 0.3194(2) 0.0164(5) Uani d . 1
C C15 0.6631(5) 0.3968(4) 0.1777(2) 0.0157(5) Uani d . 1
C C16 0.4290(5) 0.2562(5) 0.0778(2) 0.0178(5) Uani d . 1
H H1A 0.9161 0.6841 0.3866 0.016 Uiso calc R 1
H H1B 0.9174 0.4248 0.4287 0.016 Uiso calc R 1
H H2 0.3923 0.6026 0.4499 0.022 Uiso d R 1
H H3 0.8297 1.1600 0.5928 0.024 Uiso d R 1
H H4 0.9955 1.3009 0.8587 0.026 Uiso d R 1
H H5 1.0355 0.7735 0.9443 0.026 Uiso d R 1
H H3A 1.0631 0.8221 0.6580 0.015 Uiso calc R 1
H H4A 0.6330 1.0148 0.7681 0.015 Uiso calc R 1
H H5A 0.6175 0.7736 0.9247 0.017 Uiso calc R 1
H H6A 0.4773 0.3462 0.7785 0.016 Uiso calc R 1
H H6B 0.3591 0.5460 0.7251 0.016 Uiso calc R 1
H H12A 0.2032 -0.2024 0.2171 0.021 Uiso calc R 1
H H12B 0.1171 0.0610 0.2387 0.021 Uiso calc R 1
H H13A 0.4366 0.1119 0.4103 0.020 Uiso calc R 1
H H13B 0.6361 0.0313 0.3010 0.020 Uiso calc R 1
H H15A 0.8080 0.3134 0.1553 0.019 Uiso calc R 1
H H15B 0.7256 0.5786 0.1729 0.019 Uiso calc R 1
H H16A 0.2882 0.3458 0.0979 0.021 Uiso calc R 1
H H16B 0.4804 0.2608 -0.0141 0.021 Uiso calc R 1
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C6 O1 C2 113.03(16) no
C2 O2 H2 105.2 no
C3 O3 H3 105.5 no
C4 O4 H4 112.3 no
C5 O5 H5 109.1 no
C12 O11 C16 110.28(17) no
C1 N14 C15 112.40(18) no
C1 N14 C13 112.23(17) no
C15 N14 C13 108.98(17) no
O2 C2 O1 111.04(18) no
O2 C2 C1 109.26(19) no
O1 C2 C1 106.57(17) no
O2 C2 C3 108.22(17) no
O1 C2 C3 109.06(16) no
C1 C2 C3 112.71(17) no
O3 C3 C4 112.13(17) no
O3 C3 C2 111.32(17) no
C4 C3 C2 109.58(17) no
O3 C3 H3A 107.9 no
C4 C3 H3A 107.9 no
C2 C3 H3A 107.9 no
O4 C4 C5 107.62(17) no
O4 C4 C3 111.81(18) no
C5 C4 C3 111.30(17) no
O4 C4 H4A 108.7 no
C5 C4 H4A 108.7 no
C3 C4 H4A 108.7 no
O5 C5 C6 109.49(18) no
O5 C5 C4 111.32(19) no
C6 C5 C4 109.14(18) no
O5 C5 H5A 109.0 no
C6 C5 H5A 109.0 no
C4 C5 H5A 109.0 no
O1 C6 C5 110.79(18) no
O1 C6 H6A 109.5 no
C5 C6 H6A 109.5 no
O1 C6 H6B 109.5 no
C5 C6 H6B 109.5 no
H6A C6 H6B 108.1 no
O11 C12 C13 112.51(19) no
O11 C12 H12A 109.1 no
C13 C12 H12A 109.1 no
O11 C12 H12B 109.1 no
C13 C12 H12B 109.1 no
H12A C12 H12B 107.8 no
N14 C13 C12 109.47(19) no
N14 C13 H13A 109.8 no
C12 C13 H13A 109.8 no
N14 C13 H13B 109.8 no
C12 C13 H13B 109.8 no
H13A C13 H13B 108.2 no
N14 C15 C16 109.92(18) no
N14 C15 H15A 109.7 no
C16 C15 H15A 109.7 no
N14 C15 H15B 109.7 no
C16 C15 H15B 109.7 no
H15A C15 H15B 108.2 no
O11 C16 C15 111.57(19) no
O11 C16 H16A 109.3 no
C15 C16 H16A 109.3 no
O11 C16 H16B 109.3 no
C15 C16 H16B 109.3 no
H16A C16 H16B 108.0 no
N14 C1 C2 110.89(18) no
N14 C1 H1A 109.5 no
C2 C1 H1A 109.5 no
N14 C1 H1B 109.5 no
C2 C1 H1B 109.5 no
H1A C1 H1B 108.0 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C6 1.436(3) no
O1 C2 1.436(3) no
O2 C2 1.399(3) no
O2 H2 0.9112 no
O3 C3 1.424(3) no
O3 H3 0.9295 no
O4 C4 1.421(3) no
O4 H4 0.8553 no
O5 C5 1.428(3) no
O5 H5 0.9108 no
O11 C12 1.425(3) no
O11 C16 1.431(3) no
N14 C1 1.464(3) no
N14 C15 1.467(3) no
N14 C13 1.476(3) no
C2 C1 1.523(3) no
C2 C3 1.537(3) no
C3 C4 1.525(3) no
C3 H3A 1.00 no
C4 C5 1.524(3) no
C4 H4A 1.00 no
C5 C6 1.514(3) no
C5 H5A 1.00 no
C6 H6A 0.99 no
C6 H6B 0.99 no
C12 C13 1.513(3) no
C12 H12A 0.99 no
C12 H12B 0.99 no
C13 H13A 0.99 no
C13 H13B 0.99 no
C15 C16 1.508(3) no
C15 H15A 0.99 no
C15 H15B 0.99 no
C16 H16A 0.99 no
C16 H16B 0.99 no
C1 H1A 0.99 no
C1 H1B 0.99 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2 N14 . 0.91 2.06 2.652(3) 122 y
O3 H3 O1 1_565 0.93 1.99 2.874(2) 158 y
O4 H4 O5 1_565 0.86 1.98 2.785(2) 158 y
O5 H5 O11 1_666 0.91 2.01 2.897(2) 164 y
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
C6 O1 C2 O2 -57.6(2) no
C6 O1 C2 C1 -176.47(17) no
C6 O1 C2 C3 61.6(2) no
O2 C2 C3 O3 -60.2(2) no
O1 C2 C3 O3 178.93(18) no
C1 C2 C3 O3 60.8(2) no
O2 C2 C3 C4 64.4(2) no
O1 C2 C3 C4 -56.5(2) no
C1 C2 C3 C4 -174.60(18) no
O3 C3 C4 O4 -61.3(2) no
C2 C3 C4 O4 174.58(17) no
O3 C3 C4 C5 178.32(18) no
C2 C3 C4 C5 54.2(2) no
O4 C4 C5 O5 -55.4(2) no
C3 C4 C5 O5 67.4(2) no
O4 C4 C5 C6 -176.42(18) no
C3 C4 C5 C6 -53.6(2) no
C2 O1 C6 C5 -62.2(2) no
O5 C5 C6 O1 -66.0(2) no
C4 C5 C6 O1 56.1(2) no
C16 O11 C12 C13 -56.5(2) no
C1 N14 C13 C12 177.65(19) no
C15 N14 C13 C12 -57.2(2) no
O11 C12 C13 N14 57.2(3) no
C1 N14 C15 C16 -176.57(19) no
C13 N14 C15 C16 58.4(2) no
C12 O11 C16 C15 56.9(2) no
N14 C15 C16 O11 -58.8(2) no
C15 N14 C1 C2 151.84(18) no
C13 N14 C1 C2 -84.9(2) no
O2 C2 C1 N14 -37.5(2) no
O1 C2 C1 N14 82.6(2) no
C3 C2 C1 N14 -157.81(18) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 6025543
