#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/06/8100635.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_8100635
loop_
_publ_author_name
'Gültekin, Zeynep'
'Frey, Wolfgang'
'Jäger, Volker'
_publ_section_title
;
Crystal structure of (3aS,4R,5S,6R,6aS)-1-benzyl-4,5,6-trihydroxy-
5,6-O-isopropylidene-3,3a,4,5,6,6a-hexahydro-1H-cyclopent[c]isoxazole, 
C₁₆H₂₁NO₄
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              281
_journal_page_last               282
_journal_volume                  217
_journal_year                    2002
_chemical_formula_structural     'C16 H21 N1 O4'
_chemical_formula_sum            'C16 H21 N O4'
_chemical_melting_point          366.5(5)
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 110.222(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   39.820(2)
_cell_length_b                   5.3038(3)
_cell_length_c                   15.4373(9)
_cell_measurement_temperature    293(2)
_cell_volume                     3059.3(3)
_diffrn_ambient_temperature      293(2)
_exptl_crystal_density_diffrn    1.265
_refine_ls_R_factor_obs          0.0680
_refine_ls_wR_factor_obs         0.1835
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '366-367' was changed to '366.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_original_formula_sum        'C16 H21 N1 O4'
_cod_database_code               8100635
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
O1A O 0.21743(11) 0.7750(9) 0.7344(2) 0.0732(11) Uani 1 d . .
N1A N 0.23699(11) 0.5528(10) 0.7258(3) 0.0613(11) Uani 1 d . .
C1A C 0.1827(2) 0.6935(16) 0.7302(4) 0.079(2) Uani 1 d . .
H1A1 H 0.1654(2) 0.8290(16) 0.7088(4) 0.095 Uiso 1 calc R .
H1A2 H 0.1831(2) 0.6391(16) 0.7905(4) 0.095 Uiso 1 calc R .
O2A O 0.12148(9) 0.7225(13) 0.5693(3) 0.099(2) Uani 1 d . .
H2A H 0.1016(3) 0.6746(93) 0.5362(51) 0.149 Uiso 1 calc R .
C2A C 0.17314(14) 0.4734(13) 0.6619(4) 0.0671(15) Uani 1 d . .
H2A1 H 0.16375(14) 0.3300(13) 0.6864(4) 0.081 Uiso 1 calc R .
O3A O 0.20348(9) 0.3077(8) 0.4940(2) 0.0628(10) Uani 1 d . .
C3A C 0.20956(13) 0.4101(12) 0.6530(3) 0.0604(13) Uani 1 d . .
H3A H 0.21435(13) 0.2285(12) 0.6584(3) 0.072 Uiso 1 calc R .
C4A C 0.20788(11) 0.5114(11) 0.5583(3) 0.0521(11) Uani 1 d . .
H4A H 0.22842(11) 0.6186(11) 0.5624(3) 0.062 Uiso 1 calc R .
O4A O 0.16001(9) 0.5888(9) 0.4202(2) 0.0697(11) Uani 1 d . .
C5A C 0.17235(11) 0.6497(12) 0.5167(3) 0.0568(12) Uani 1 d . .
H5A H 0.17552(11) 0.8321(12) 0.5263(3) 0.068 Uiso 1 calc R .
C6A C 0.14795(12) 0.5451(14) 0.5647(3) 0.0654(14) Uani 1 d . .
H6A H 0.13605(12) 0.3931(14) 0.5323(3) 0.079 Uiso 1 calc R .
C7A C 0.18431(12) 0.4122(12) 0.4042(3) 0.0602(13) Uani 1 d . .
C8A C 0.1640(2) 0.2028(16) 0.3433(4) 0.099(2) Uani 1 d . .
H8A1 H 0.1805(2) 0.0850(16) 0.3330(4) 0.148 Uiso 1 calc R .
H8A2 H 0.1489(2) 0.2710(16) 0.2853(4) 0.148 Uiso 1 calc R .
H8A3 H 0.1495(2) 0.1181(16) 0.3728(4) 0.148 Uiso 1 calc R .
C9A C 0.2094(2) 0.5464(17) 0.3659(4) 0.081(2) Uani 1 d . .
H9A1 H 0.2257(2) 0.4268(17) 0.3553(4) 0.122 Uiso 1 calc R .
H9A2 H 0.2227(2) 0.6713(17) 0.4093(4) 0.122 Uiso 1 calc R .
H9A3 H 0.1959(2) 0.6267(17) 0.3088(4) 0.122 Uiso 1 calc R .
C10A C 0.2488(2) 0.4180(13) 0.8139(3) 0.072(2) Uani 1 d . .
H10A H 0.2595(2) 0.2591(13) 0.8061(3) 0.086 Uiso 1 calc R .
H10B H 0.2282(2) 0.3803(13) 0.8311(3) 0.086 Uiso 1 calc R .
C11A C 0.27547(14) 0.5637(13) 0.8906(3) 0.0624(13) Uani 1 d . .
C12A C 0.29410(15) 0.7688(15) 0.8751(4) 0.071(2) Uani 1 d . .
H12A H 0.29000(15) 0.8216(15) 0.8149(4) 0.086 Uiso 1 calc R .
C13A C 0.3187(2) 0.8971(16) 0.9474(4) 0.083(2) Uani 1 d . .
H13A H 0.3307(2) 1.0360(16) 0.9355(4) 0.100 Uiso 1 calc R .
C14A C 0.3255(2) 0.8207(20) 1.0362(4) 0.092(2) Uani 1 d . .
H14A H 0.3424(2) 0.9051(20) 1.0846(4) 0.111 Uiso 1 calc R .
C15A C 0.3076(2) 0.6217(20) 1.0533(4) 0.094(2) Uani 1 d . .
H15A H 0.3120(2) 0.5705(20) 1.1139(4) 0.113 Uiso 1 calc R .
C16A C 0.2827(2) 0.4933(17) 0.9815(3) 0.080(2) Uani 1 d . .
H16A H 0.2705(2) 0.3570(17) 0.9946(3) 0.097 Uiso 1 calc R .
O1B O -0.04485(9) 0.7381(7) 0.7741(2) 0.0540(8) Uani 1 d . .
N1B N -0.03291(9) 0.5082(8) 0.8264(2) 0.0476(9) Uani 1 d . .
C1B C -0.06860(12) 0.6651(12) 0.6836(3) 0.0569(12) Uani 1 d . .
H1B1 H -0.06869(12) 0.7912(12) 0.6380(3) 0.068 Uiso 1 calc R .
H1B2 H -0.09283(12) 0.6436(12) 0.6833(3) 0.068 Uiso 1 calc R .
O2B O -0.05095(8) 0.5903(10) 0.5204(2) 0.0658(11) Uani 1 d . .
H2B H -0.0429(14) 0.5621(105) 0.4791(18) 0.099 Uiso 1 calc R .
C2B C -0.05361(11) 0.4143(10) 0.6633(3) 0.0470(10) Uani 1 d . .
H2B1 H -0.07242(11) 0.2864(10) 0.6413(3) 0.056 Uiso 1 calc R .
O3B O 0.02959(8) 0.1946(8) 0.7387(2) 0.0596(9) Uani 1 d . .
C3B C -0.02593(10) 0.3426(10) 0.7587(2) 0.0464(10) Uani 1 d . .
H3B H -0.02723(10) 0.1638(10) 0.7733(2) 0.056 Uiso 1 calc R .
O4B O 0.03242(7) 0.4757(7) 0.6306(2) 0.0523(8) Uani 1 d . .
C4B C 0.01049(11) 0.4133(10) 0.7518(3) 0.0458(10) Uani 1 d . .
H4B H 0.02492(11) 0.5166(10) 0.8041(3) 0.055 Uiso 1 calc R .
C5B C 0.00317(10) 0.5466(11) 0.6596(2) 0.0453(10) Uani 1 d . .
H5B H 0.00192(10) 0.7298(11) 0.6660(2) 0.054 Uiso 1 calc R .
C6B C -0.03246(10) 0.4390(11) 0.5990(2) 0.0486(11) Uani 1 d . .
H6B H -0.02856(10) 0.2707(11) 0.5781(2) 0.058 Uiso 1 calc R .
C7B C 0.05271(12) 0.2821(12) 0.6923(3) 0.0551(12) Uani 1 d . .
C8B C 0.0590(2) 0.0702(14) 0.6336(5) 0.084(2) Uani 1 d . .
H8B1 H 0.0746(2) 0.1281(14) 0.6022(5) 0.126 Uiso 1 calc R .
H8B2 H 0.0365(2) 0.0186(14) 0.5891(5) 0.126 Uiso 1 calc R .
H8B3 H 0.0699(2) -0.0702(14) 0.6724(5) 0.126 Uiso 1 calc R .
C9B C 0.08660(13) 0.3965(20) 0.7578(4) 0.090(3) Uani 1 d . .
H9B1 H 0.10133(13) 0.4527(20) 0.7238(4) 0.136 Uiso 1 calc R .
H9B2 H 0.09932(13) 0.2724(20) 0.8023(4) 0.136 Uiso 1 calc R .
H9B3 H 0.08074(13) 0.5372(20) 0.7890(4) 0.136 Uiso 1 calc R .
C10B C -0.06227(12) 0.4129(12) 0.8557(3) 0.0572(12) Uani 1 d . .
H10C H -0.05431(12) 0.2637(12) 0.8936(3) 0.069 Uiso 1 calc R .
H10D H -0.08252(12) 0.3662(12) 0.8018(3) 0.069 Uiso 1 calc R .
C11B C -0.07363(12) 0.6116(12) 0.9098(3) 0.0569(13) Uani 1 d . .
C12B C -0.0508(2) 0.6859(15) 0.9962(3) 0.072(2) Uani 1 d . .
H12B H -0.0287(2) 0.6078(15) 1.0224(3) 0.086 Uiso 1 calc R .
C13B C -0.0609(2) 0.8768(15) 1.0437(4) 0.084(2) Uani 1 d . .
H13B H -0.0454(2) 0.9268(15) 1.1015(4) 0.100 Uiso 1 calc R .
C14B C -0.0934(2) 0.9915(17) 1.0060(5) 0.089(2) Uani 1 d . .
H14B H -0.1001(2) 1.1178(17) 1.0386(5) 0.107 Uiso 1 calc R .
C15B C -0.1162(2) 0.9218(17) 0.9206(5) 0.087(2) Uani 1 d . .
H15B H -0.1382(2) 1.0012(17) 0.8947(5) 0.104 Uiso 1 calc R .
C16B C -0.10615(13) 0.7332(15) 0.8737(4) 0.071(2) Uani 1 d . .
H16B H -0.12176(13) 0.6859(15) 0.8157(4) 0.085 Uiso 1 calc R .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C1A 1.429(7) . ?
O1A N1A 1.444(7) . ?
N1A C10A 1.462(6) . ?
N1A C3A 1.477(7) . ?
C1A C2A 1.531(9) . ?
C1A H1A1 0.97 . ?
C1A H1A2 0.97 . ?
O2A C6A 1.433(8) . ?
O2A H2A 0.82 . ?
C2A C6A 1.537(7) . ?
C2A C3A 1.541(7) . ?
C2A H2A1 0.98 . ?
O3A C4A 1.437(6) . ?
O3A C7A 1.442(5) . ?
C3A C4A 1.536(6) . ?
C3A H3A 0.98 . ?
C4A C5A 1.524(6) . ?
C4A H4A 0.98 . ?
O4A C7A 1.428(7) . ?
O4A C5A 1.436(6) . ?
C5A C6A 1.516(7) . ?
C5A H5A 0.98 . ?
C6A H6A 0.98 . ?
C7A C8A 1.499(9) . ?
C7A C9A 1.504(8) . ?
C8A H8A1 0.96 . ?
C8A H8A2 0.96 . ?
C8A H8A3 0.96 . ?
C9A H9A1 0.96 . ?
C9A H9A2 0.96 . ?
C9A H9A3 0.96 . ?
C10A C11A 1.502(8) . ?
C10A H10A 0.97 . ?
C10A H10B 0.97 . ?
C11A C12A 1.383(10) . ?
C11A C16A 1.384(7) . ?
C12A C13A 1.384(9) . ?
C12A H12A 0.93 . ?
C13A C14A 1.363(9) . ?
C13A H13A 0.93 . ?
C14A C15A 1.351(12) . ?
C14A H14A 0.93 . ?
C15A C16A 1.385(10) . ?
C15A H15A 0.93 . ?
C16A H16A 0.93 . ?
O1B C1B 1.443(5) . ?
O1B N1B 1.449(5) . ?
N1B C3B 1.464(6) . ?
N1B C10B 1.481(6) . ?
C1B C2B 1.534(7) . ?
C1B H1B1 0.97 . ?
C1B H1B2 0.97 . ?
O2B C6B 1.428(5) . ?
O2B H2B 0.82 . ?
C2B C6B 1.512(5) . ?
C2B C3B 1.551(5) . ?
C2B H2B1 0.98 . ?
O3B C7B 1.425(5) . ?
O3B C4B 1.439(6) . ?
C3B C4B 1.537(5) . ?
C3B H3B 0.98 . ?
O4B C5B 1.435(4) . ?
O4B C7B 1.443(6) . ?
C4B C5B 1.524(6) . ?
C4B H4B 0.98 . ?
C5B C6B 1.515(6) . ?
C5B H5B 0.98 . ?
C6B H6B 0.98 . ?
C7B C9B 1.506(8) . ?
C7B C8B 1.518(9) . ?
C8B H8B1 0.96 . ?
C8B H8B2 0.96 . ?
C8B H8B3 0.96 . ?
C9B H9B1 0.96 . ?
C9B H9B2 0.96 . ?
C9B H9B3 0.96 . ?
C10B C11B 1.507(7) . ?
C10B H10C 0.97 . ?
C10B H10D 0.97 . ?
C11B C16B 1.380(8) . ?
C11B C12B 1.387(7) . ?
C12B C13B 1.388(9) . ?
C12B H12B 0.93 . ?
C13B C14B 1.366(9) . ?
C13B H13B 0.93 . ?
C14B C15B 1.368(10) . ?
C14B H14B 0.93 . ?
C15B C16B 1.374(10) . ?
C15B H15B 0.93 . ?
C16B H16B 0.93 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653821
