#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/38/2203817.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_2203817
loop_
_publ_author_name
'Metta-Magaña, Alejandro J.'
'Tlahuext, Hugo'
'Reyes-Martínez, Reyna'
_publ_section_title
;
 N-Isopropyl-α-glucoheptonamide
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1046
_journal_page_last               o1048
_journal_paper_doi               10.1107/S1600536804011821
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C10 H21 N O7'
_chemical_formula_moiety         'C10 H21 N O7'
_chemical_formula_sum            'C10 H21 N O7'
_chemical_formula_weight         267.28
_chemical_melting_point          534
_chemical_name_common            isopropylglucoheptonamide
_chemical_name_systematic        N-isopropyl-D-glycero-D-gulo-heptonamide
_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
_cell_angle_beta                 90.664(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.866(2)
_cell_length_b                   22.435(9)
_cell_length_c                   6.040(2)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.3
_cell_measurement_theta_min      3.5
_cell_volume                     659.3(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker 2000a)'
_computing_data_reduction        'SAINT (Bruker 2000b)'
_computing_molecular_graphics    'SHELXTL (Bruker 2000c)'
_computing_publication_material
'SHELXTL and enCIFer v1.1 (Allen et al. 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω 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  0.037
_diffrn_reflns_av_sigmaI/netI    0.033
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            3915
_diffrn_reflns_theta_full        27.3
_diffrn_reflns_theta_max         27.3
_diffrn_reflns_theta_min         1.8
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'trigonal prismatic'
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.00
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1504
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.00
_refine_ls_R_factor_all          0.048
_refine_ls_R_factor_gt           0.044
_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)+(0.0755P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.110
_refine_ls_wR_factor_ref         0.113
_reflns_number_gt                1361
_reflns_number_total             1504
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk6166.cif
_cod_data_source_block           I
_cod_original_cell_volume        659.3(5)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2203817
_cod_database_fobs_code          2203817
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_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
_atom_site_type_symbol
C1 0.1920(6) 0.37616(12) 0.1509(4) 0.0347(6) Uani d . 1 C
C2 0.0042(6) 0.40484(13) -0.0215(5) 0.0351(6) Uani d . 1 C
C3 0.1732(6) 0.44277(13) -0.1800(4) 0.0312(6) Uani d . 1 C
C4 0.3208(6) 0.49653(12) -0.0772(4) 0.0306(6) Uani d . 1 C
C5 0.1398(5) 0.53999(11) 0.0456(4) 0.0284(5) Uani d . 1 C
C6 0.3119(6) 0.58734(12) 0.1655(4) 0.0322(6) Uani d . 1 C
C7 0.1397(6) 0.63217(13) 0.2891(5) 0.0393(7) Uani d . 1 C
C8 0.3943(8) 0.28165(14) 0.2836(6) 0.0473(8) Uani d . 1 C
C9 0.4991(11) 0.2294(2) 0.1520(7) 0.0738(13) Uani d . 1 C
H9A 0.6325 0.2079 0.2388 0.089 Uiso calc R 1 H
H9B 0.5829 0.2437 0.0189 0.089 Uiso calc R 1 H
H9C 0.3487 0.2035 0.1144 0.089 Uiso calc R 1 H
C10 0.2483(11) 0.26276(18) 0.4913(7) 0.0716(12) Uani d . 1 C
H10A 0.1703 0.2971 0.5614 0.086 Uiso calc R 1 H
H10B 0.3771 0.2441 0.5909 0.086 Uiso calc R 1 H
H10C 0.1047 0.2351 0.4538 0.086 Uiso calc R 1 H
N1 0.2133(6) 0.31719(12) 0.1412(4) 0.0420(6) Uani d . 1 N
O1 0.3181(6) 0.40739(10) 0.2843(3) 0.0533(6) Uani d . 1 O
O2 -0.1400(4) 0.35979(10) -0.1387(4) 0.0479(6) Uani d . 1 O
O3 0.3726(4) 0.40529(10) -0.2765(3) 0.0418(5) Uani d . 1 O
O4 0.4498(4) 0.52732(10) -0.2547(3) 0.0384(5) Uani d . 1 O
O5 -0.0524(4) 0.56883(8) -0.1012(3) 0.0331(4) Uani d . 1 O
O6 0.5062(4) 0.55920(10) 0.3101(3) 0.0387(5) Uani d . 1 O
O7 -0.0088(4) 0.60602(10) 0.4627(3) 0.0399(5) Uani d . 1 O
H2 -0.1280 0.4300 0.0415 0.048 Uiso d R 1 H
H3 0.0504 0.4562 -0.2844 0.048 Uiso d R 1 H
H4 0.4601 0.4844 0.0130 0.048 Uiso d R 1 H
H5 0.0329 0.5188 0.1492 0.048 Uiso d R 1 H
H6 0.4209 0.6069 0.0450 0.048 Uiso d R 1 H
H7A -0.0093 0.6513 0.1858 0.048 Uiso d R 1 H
H7B 0.2584 0.6574 0.3478 0.048 Uiso d R 1 H
H8 0.5441 0.3064 0.3160 0.048 Uiso d R 1 H
H1N 0.1381 0.3018 0.0446 0.060 Uiso d R 1 H
H2O -0.2894 0.3733 -0.1674 0.060 Uiso d R 1 H
H3O 0.3644 0.4107 -0.3932 0.060 Uiso d R 1 H
H4O 0.6034 0.5377 -0.2123 0.060 Uiso d R 1 H
H5O 0.0172 0.5767 -0.2111 0.060 Uiso d R 1 H
H6O 0.4309 0.5462 0.4059 0.060 Uiso d R 1 H
H7O -0.1650 0.5970 0.4242 0.060 Uiso d R 1 H
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
O1 C1 N1 124.0(3) yes
O1 C1 C2 120.0(2) yes
N1 C1 C2 116.0(2) yes
O2 C2 C1 109.3(2) ?
O2 C2 C3 110.6(2) ?
C1 C2 C3 109.9(2) yes
O2 C2 H2 107.1 ?
C1 C2 H2 112.6 ?
C3 C2 H2 107.2 ?
O3 C3 C2 107.7(2) ?
O3 C3 C4 108.3(2) ?
C2 C3 C4 116.0(2) yes
O3 C3 H3 111.0 ?
C2 C3 H3 105.3 ?
C4 C3 H3 108.6 ?
O4 C4 C5 108.6(2) ?
O4 C4 C3 106.5(2) ?
C5 C4 C3 115.7(2) yes
O4 C4 H4 105.4 ?
C5 C4 H4 109.6 ?
C3 C4 H4 110.5 ?
O5 C5 C4 111.5(2) ?
O5 C5 C6 109.2(2) yes
C4 C5 C6 111.1(2) yes
O5 C5 H5 106.0 ?
C4 C5 H5 109.1 ?
C6 C5 H5 109.8 ?
O6 C6 C7 111.0(2) ?
O6 C6 C5 109.7(2) ?
C7 C6 C5 113.1(2) yes
O6 C6 H6 106.5 ?
C7 C6 H6 111.6 ?
C5 C6 H6 104.5 ?
O7 C7 C6 112.5(2) ?
O7 C7 H7A 104.9 ?
C6 C7 H7A 111.3 ?
O7 C7 H7B 107.9 ?
C6 C7 H7B 105.2 ?
H7A C7 H7B 115.2 ?
N1 C8 C9 108.6(3) yes
N1 C8 C10 110.9(3) ?
C9 C8 C10 112.7(3) ?
N1 C8 H8 105.2 ?
C9 C8 H8 107.6 ?
C10 C8 H8 111.5 ?
C8 C9 H9A 109.5 ?
C8 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
C8 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
C8 C10 H10A 109.5 ?
C8 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
C8 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
C1 N1 C8 124.4(3) yes
C1 N1 H1N 116.4 yes
C8 N1 H1N 118.8 yes
C2 O2 H2O 106.2 ?
C3 O3 H3O 106.0 ?
C4 O4 H4O 108.0 ?
C5 O5 H5O 110.2 ?
C6 O6 H6O 108.6 ?
C7 O7 H7O 112.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.227(3) yes
C1 N1 1.328(4) yes
C1 C2 1.521(4) yes
C2 O2 1.415(3) yes
C2 C3 1.528(4) yes
C2 H2 0.9393 ?
C3 O3 1.414(3) yes
C3 C4 1.532(4) yes
C3 H3 0.9148 ?
C4 O4 1.427(3) yes
C4 C5 1.514(4) yes
C4 H4 0.9061 ?
C5 O5 1.435(3) yes
C5 C6 1.530(4) yes
C5 H5 0.9468 ?
C6 O6 1.427(3) yes
C6 C7 1.512(4) yes
C6 H6 1.0056 ?
C7 O7 1.408(4) yes
C7 H7A 1.0434 ?
C7 H7B 0.8795 ?
C8 N1 1.461(4) yes
C8 C9 1.508(5) yes
C8 C10 1.510(6) yes
C8 H8 0.9348 ?
C9 H9A 0.9600 ?
C9 H9B 0.9600 ?
C9 H9C 0.9600 ?
C10 H10A 0.9600 ?
C10 H10B 0.9600 ?
C10 H10C 0.9600 ?
N1 H1N 0.7671 yes
O2 H2O 0.8044 ?
O3 H3O 0.7159 ?
O4 H4O 0.8214 ?
O5 H5O 0.7687 ?
O6 H6O 0.7471 ?
O7 H7O 0.8180 ?
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
N1 H1N O2 . 0.77 2.17 2.581(3) 114
O5 H5O O4 . 0.77 2.40 2.784(3) 113
O6 H6O O7 . 0.75 2.55 2.878(3) 109
O2 H2O O3 1_455 0.80 1.91 2.704(3) 172
O3 H3O O1 1_554 0.72 1.96 2.663(3) 168
O4 H4O O5 1_655 0.82 1.93 2.746(3) 175
O5 H5O O7 1_554 0.77 2.08 2.773(3) 150
O6 H6O O4 1_556 0.75 2.09 2.741(3) 145
O7 H7O O6 1_455 0.82 1.93 2.734(3) 167
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
O1 C1 C2 O2 -173.6(3) ?
N1 C1 C2 O2 8.3(3) yes
O1 C1 C2 C3 64.8(3) ?
N1 C1 C2 C3 -113.3(3) yes
O2 C2 C3 O3 -63.4(3) ?
C1 C2 C3 O3 57.4(3) ?
O2 C2 C3 C4 175.1(2) ?
C1 C2 C3 C4 -64.1(3) yes
O3 C3 C4 O4 62.4(2) ?
C2 C3 C4 O4 -176.4(2) ?
O3 C3 C4 C5 -176.7(2) ?
C2 C3 C4 C5 -55.6(3) yes
O4 C4 C5 O5 54.6(3) ?
C3 C4 C5 O5 -65.1(3) ?
O4 C4 C5 C6 -67.5(2) ?
C3 C4 C5 C6 172.9(2) yes
O5 C5 C6 O6 -179.30(19) ?
C4 C5 C6 O6 -55.9(2) ?
O5 C5 C6 C7 56.1(3) ?
C4 C5 C6 C7 179.5(2) yes
O6 C6 C7 O7 -59.7(3) ?
C5 C6 C7 O7 64.2(3) ?
O1 C1 N1 C8 -1.6(5) yes
C2 C1 N1 C8 176.5(3) yes
C9 C8 N1 C1 -145.4(4) ?
C10 C8 N1 C1 90.3(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21174207
