#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/40/2004098.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_2004098
loop_
_publ_author_name
'Merino, P.'
'Merchan, F. L.'
'Tejero, T.'
_publ_section_title
;Chiral Hydroxylamines. I.
 1-(N-Benzyl-N-hydroxyamino)-1-deoxy-2,3-O-isopropylidene-1-(1-methylimidazol-2-yl)-<small>D</small>-threo-triitol
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2400
_journal_page_last               2401
_journal_paper_doi               10.1107/S0108270195006962
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C17 H23 N3 O3'
_chemical_formula_sum            'C17 H23 N3 O3'
_chemical_formula_weight         317.38
_chemical_melting_point          376
_chemical_name_systematic
;
N-Benzyl-1-deoxy-1-(hydroxyamino)-2,3-O-diisopropylidene-1-
(N-methylimidazol-2-yl)-D-threo-triitol.
;
_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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.388(2)
_cell_length_b                   10.527(2)
_cell_length_c                   19.730(4)
_cell_measurement_reflns_used    62
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.656
_cell_measurement_theta_min      6.623
_cell_volume                     1742.2(6)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1992)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990b)'
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990a)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       'Profile data from 2θ/ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            1822
_diffrn_reflns_theta_max         22.55
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        3.70
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       'Transparent block'
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.147
_refine_ls_extinction_coef       0.0103(17)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.029
_refine_ls_goodness_of_fit_obs   1.063
_refine_ls_hydrogen_treatment    'H atoms refined as riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         1659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_restrained_S_obs      1.063
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_obs          0.0467
_refine_ls_shift/esd_max         -0.021
_refine_ls_shift/esd_mean        0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(F~o~^2^) + (0.0524P)^2^ + 0.5028P]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.1251
_refine_ls_wR_factor_obs         0.1027
_reflns_number_observed          1120
_reflns_number_total             1659
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            bk1141.cif
_cod_data_source_block           gly3
_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               2004098
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_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
O2 1 0.0258(4) 0.1100(3) 0.5841(2) 0.0582(11) Uani d . O
N2 1 0.2508(5) 0.1032(4) 0.4522(2) 0.0523(12) Uani d . N
O1 1 -0.1923(4) -0.1630(3) 0.4750(2) 0.0596(11) Uani d . O
H(O) 1 -0.2190 -0.2318 0.4909 0.058(18) Uiso calc R H
N3 1 0.3036(5) -0.0913(4) 0.4818(2) 0.0547(12) Uani d . N
N1 1 -0.0216(5) -0.1590(4) 0.4683(2) 0.0481(12) Uani d . N
C5 1 0.0174(6) -0.0294(4) 0.4876(3) 0.0465(14) Uani d . C
H5 1 -0.0449 0.0298 0.4599 0.077(8) Uiso calc R H
C1 1 0.1911(6) -0.0081(5) 0.4748(3) 0.0466(13) Uani d . C
C3 1 0.4096(7) 0.0876(6) 0.4452(3) 0.069(2) Uani d . C
H3 1 0.4827 0.1480 0.4305 0.092(8) Uiso calc R H
C7 1 0.0549(9) -0.1007(5) 0.6110(3) 0.072(2) Uani d . C
H7A 1 -0.0138 -0.1719 0.6219 0.077(8) Uiso calc R H
H7B 1 0.1537 -0.1329 0.5920 0.077(8) Uiso calc R H
C4 1 0.1661(8) 0.2206(5) 0.4378(3) 0.074(2) Uani d . C
H4A 1 0.2404 0.2838 0.4225 0.138(10) Uiso calc R H
H4B 1 0.1139 0.2498 0.4782 0.138(10) Uiso calc R H
H4C 1 0.0881 0.2056 0.4031 0.138(10) Uiso calc R H
C6 1 -0.0263(7) -0.0117(5) 0.5619(3) 0.0533(14) Uani d . C
H6 1 -0.1422 -0.0183 0.5673 0.077(8) Uiso calc R H
C8 1 0.1097(9) 0.0992(6) 0.6461(3) 0.075(2) Uani d . C
C12 1 -0.0270(9) -0.0932(6) 0.3448(3) 0.065(2) Uani d . C
O3 1 0.0845(6) -0.0266(4) 0.6684(2) 0.096(2) Uani d . O
C11 1 0.0142(7) -0.1909(5) 0.3980(3) 0.062(2) Uani d . C
H11A 1 -0.0417 -0.2688 0.3869 0.077(8) Uiso calc R H
H11B 1 0.1275 -0.2086 0.3947 0.077(8) Uiso calc R H
C2 1 0.4412(7) -0.0327(6) 0.4638(3) 0.068(2) Uani d . C
H2 1 0.5417 -0.0700 0.4643 0.092(8) Uiso calc R H
C17 1 0.0879(10) -0.0207(7) 0.3153(3) 0.091(2) Uani d . C
H17 1 0.1942 -0.0327 0.3271 0.092(8) Uiso calc R H
C9 1 0.0365(10) 0.1823(7) 0.6985(3) 0.105(3) Uani d . C
H9A 1 0.0500 0.2697 0.6858 0.138(10) Uiso calc R H
H9B 1 0.0873 0.1674 0.7414 0.138(10) Uiso calc R H
H9C 1 -0.0752 0.1635 0.7021 0.138(10) Uiso calc R H
C13 1 -0.1809(9) -0.0752(6) 0.3250(3) 0.077(2) Uani d . C
H13 1 -0.2611 -0.1255 0.3434 0.092(8) Uiso calc R H
C16 1 0.0484(16) 0.0694(9) 0.2686(4) 0.114(3) Uani d . C
H16 1 0.1283 0.1178 0.2486 0.092(8) Uiso calc R H
C10 1 0.2807(8) 0.1264(9) 0.6338(4) 0.106(3) Uani d . C
H10A 1 0.2926 0.2125 0.6187 0.138(10) Uiso calc R H
H10B 1 0.3208 0.0697 0.5997 0.138(10) Uiso calc R H
H10C 1 0.3394 0.1144 0.6751 0.138(10) Uiso calc R H
C15 1 -0.1046(16) 0.0894(9) 0.2509(4) 0.122(4) Uani d . C
H15 1 -0.1310 0.1531 0.2203 0.092(8) Uiso calc R H
C14 1 -0.2189(11) 0.0158(8) 0.2784(4) 0.106(3) Uani d . C
H14 1 -0.3246 0.0269 0.2654 0.092(8) Uiso calc R 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
C8 O2 C6 110.2(4) yes
C1 N2 C3 107.2(5) yes
C1 N2 C4 128.4(4) yes
C3 N2 C4 124.5(5) yes
C1 N3 C2 106.6(4) yes
O1 N1 C5 103.1(4) yes
O1 N1 C11 106.6(4) ?
C5 N1 C11 114.7(4) ?
N1 C5 C1 108.4(4) yes
N1 C5 C6 108.2(4) ?
C1 C5 C6 112.2(5) ?
N3 C1 N2 110.5(4) yes
N3 C1 C5 126.2(5) ?
N2 C1 C5 123.2(5) ?
C2 C3 N2 106.3(5) yes
O3 C7 C6 104.7(4) yes
O2 C6 C7 102.9(4) yes
O2 C6 C5 109.4(4) ?
C7 C6 C5 115.7(4) yes
O3 C8 O2 105.7(5) yes
O3 C8 C10 112.1(7) ?
O2 C8 C10 109.0(6) ?
O3 C8 C9 105.8(6) ?
O2 C8 C9 110.4(6) ?
C10 C8 C9 113.6(7) ?
C13 C12 C17 118.0(7) ?
C13 C12 C11 120.8(6) ?
C17 C12 C11 121.2(7) ?
C7 O3 C8 107.2(4) yes
N1 C11 C12 117.2(4) ?
C3 C2 N3 109.4(5) yes
C12 C17 C16 120.5(9) ?
C12 C13 C14 120.8(8) ?
C15 C16 C17 121.0(10) ?
C14 C15 C16 119.0(10) ?
C15 C14 C13 120.6(9) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O2 C8 1.416(6) yes
O2 C6 1.423(6) yes
N2 C1 1.350(6) yes
N2 C3 1.349(7) yes
N2 C4 1.454(6) yes
O1 N1 1.439(5) yes
N3 C1 1.295(6) yes
N3 C2 1.355(6) yes
N1 C5 1.454(6) yes
N1 C11 1.459(6) yes
C5 C1 1.495(7) yes
C5 C6 1.523(7) yes
C3 C2 1.345(8) yes
C7 O3 1.399(7) yes
C7 C6 1.509(7) yes
C8 O3 1.412(7) yes
C8 C10 1.482(9) yes
C8 C9 1.488(9) yes
C12 C13 1.362(9) yes
C12 C17 1.360(8) yes
C12 C11 1.509(8) yes
C17 C16 1.364(11) yes
C13 C14 1.365(10) yes
C16 C15 1.346(11) yes
C15 C14 1.346(12) yes
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 C1 N3 C2 178.9(6) yes
C1 N3 C2 C3 -0.5(6) yes
N3 C2 C3 N2 0.3(7) yes
C2 C3 N2 C4 179.6(5) yes
N1 C11 C12 C13 -75.8(7) ?
C11 C12 C13 C14 178.0(5) ?
C12 C13 C14 C15 0.1(11) ?
C13 C14 C15 C16 2.1(13) ?
C14 C15 C16 C17 -2.4(15) ?
C5 C6 C7 O3 143.0(5) ?
C6 C7 O3 C8 -31.2(7) yes
C7 O3 C8 O2 26.3(7) yes
O3 C8 O2 C9 114.0(8) ?
C8 O2 C9 C10 32.9(6) ?
N1 C5 C6 C7 58.4(6) yes
N1 C5 C6 O2 174.1(4) yes
C1 C5 N1 C11 -57.9(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21187137
