#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/28/8102801.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_8102801
loop_
_publ_author_name
'Wolfgang Frey'
'Hua Yang'
'Volker Jäger'
_publ_section_title
;
 Crystal structure of
 (3R,4R,5R,6S,1'R)-2-benzyl-3-methyl-4,5-O-isopropylidene-dioxy-6-(1'-nitroethyl)-tetrahydro-1,2-oxazine,
 C17H24N2O5
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              589
_journal_volume                  225
_journal_year                    2010
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C17 H24 N2 O5'
_chemical_formula_sum            'C17 H24 N2 O5'
_chemical_formula_weight         336.38
_chemical_name_systematic
; 
(3R,4R,5R,6S,1'R)-2-benzyl-3-methyl-4,5-O-isopropylidene-
dioxy-6-(1'-nitroethyl)-tetrahydro-1,2-oxazine
;
_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                   5.4614(11)
_cell_length_b                   17.508(4)
_cell_length_c                   18.562(3)
_cell_measurement_reflns_used    26
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17
_cell_measurement_theta_min      15
_cell_volume                     1774.9(6)
_computing_cell_refinement       'Siemens P3/PC Data Collection System'
_computing_data_collection       'Siemens P3/PC Data Collection System'
_computing_data_reduction        'SHELXTL-plus, XDISK (Sheldrick, 1991)'
_computing_molecular_graphics    'SHELXTL-plus, XP (Sheldrick, 1991)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nicolet P3'
_diffrn_measurement_method       Wyckoff-Scan
_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  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5818
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.60
_diffrn_standards_decay_%        5
_diffrn_standards_interval_count 50
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.9(12)
_refine_ls_extinction_coef       0.039(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         5186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0485
_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)+(0.0628P)²+0.1806P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1354
_reflns_number_gt                4025
_reflns_number_total             5186
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-3112.cff
_cod_data_source_block           wf1470yh
_cod_database_code               8102801
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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0980(2) 0.29230(7) 0.75701(6) 0.0554(3) Uani 1 1 d . . .
N1 N 0.0723(3) 0.24683(8) 0.80180(7) 0.0528(3) Uani 1 1 d . . .
C1 C 0.0325(3) 0.32425(9) 0.69799(9) 0.0505(4) Uani 1 1 d . . .
H1 H -0.0863 0.3519 0.6682 0.061 Uiso 1 1 calc R . .
O2 O 0.2313(3) 0.13419(7) 0.64217(7) 0.0612(3) Uani 1 1 d . . .
C2 C 0.1449(3) 0.26258(9) 0.65108(8) 0.0507(4) Uani 1 1 d . . .
H2 H 0.2703 0.2847 0.6196 0.061 Uiso 1 1 calc R . .
N2 N 0.3083(4) 0.42767(9) 0.65850(10) 0.0640(4) Uani 1 1 d . . .
O3 O -0.0404(3) 0.22668(7) 0.60895(6) 0.0581(3) Uani 1 1 d . . .
C3 C 0.2502(3) 0.19542(9) 0.69249(9) 0.0516(4) Uani 1 1 d . . .
H3 H 0.4225 0.2050 0.7042 0.062 Uiso 1 1 calc R . .
C4 C 0.1079(4) 0.17539(9) 0.76061(9) 0.0537(4) Uani 1 1 d . . .
H4 H -0.0520 0.1543 0.7473 0.064 Uiso 1 1 calc R . .
O4 O 0.1570(4) 0.45386(15) 0.61880(12) 0.1213(9) Uani 1 1 d . . .
C5 C 0.2495(5) 0.11640(12) 0.80415(12) 0.0765(6) Uani 1 1 d . . .
H5A H 0.3878 0.1404 0.8266 0.115 Uiso 1 1 calc R . .
H5B H 0.3052 0.0764 0.7728 0.115 Uiso 1 1 calc R . .
H5C H 0.1447 0.0952 0.8405 0.115 Uiso 1 1 calc R . .
O5 O 0.5261(4) 0.43628(12) 0.64921(13) 0.1040(7) Uani 1 1 d . . .
C6 C 0.0569(4) 0.15449(10) 0.58726(10) 0.0566(4) Uani 1 1 d . . .
C7 C 0.1936(6) 0.16085(14) 0.51621(11) 0.0785(7) Uani 1 1 d . . .
H7A H 0.2571 0.1117 0.5030 0.118 Uiso 1 1 calc R . .
H7B H 0.3263 0.1964 0.5213 0.118 Uiso 1 1 calc R . .
H7C H 0.0836 0.1785 0.4794 0.118 Uiso 1 1 calc R . .
C8 C -0.1493(4) 0.09768(14) 0.58524(15) 0.0768(6) Uani 1 1 d . . .
H8A H -0.0873 0.0487 0.5708 0.115 Uiso 1 1 calc R . .
H8B H -0.2710 0.1144 0.5514 0.115 Uiso 1 1 calc R . .
H8C H -0.2214 0.0936 0.6323 0.115 Uiso 1 1 calc R . .
C9 C 0.2240(4) 0.38220(10) 0.72311(9) 0.0564(4) Uani 1 1 d . . .
H9 H 0.3644 0.3546 0.7432 0.068 Uiso 1 1 calc R . .
C10 C 0.1302(6) 0.43812(13) 0.77875(12) 0.0825(8) Uani 1 1 d . . .
H10A H 0.2460 0.4789 0.7844 0.124 Uiso 1 1 calc R . .
H10B H 0.1089 0.4123 0.8240 0.124 Uiso 1 1 calc R . .
H10C H -0.0240 0.4586 0.7632 0.124 Uiso 1 1 calc R . .
C11 C -0.0741(5) 0.23301(12) 0.86734(10) 0.0689(5) Uani 1 1 d . . .
H11A H 0.0101 0.1958 0.8971 0.083 Uiso 1 1 calc R . .
H11B H -0.2304 0.2111 0.8535 0.083 Uiso 1 1 calc R . .
C12 C -0.1203(4) 0.30387(12) 0.91151(9) 0.0591(4) Uani 1 1 d . . .
C13 C -0.3283(4) 0.34671(16) 0.90333(12) 0.0777(6) Uani 1 1 d . . .
H13 H -0.4443 0.3329 0.8691 0.093 Uiso 1 1 calc R . .
C14 C -0.3667(5) 0.41084(17) 0.94606(15) 0.0889(8) Uani 1 1 d . . .
H14 H -0.5069 0.4402 0.9394 0.107 Uiso 1 1 calc R . .
C15 C -0.1997(5) 0.43134(14) 0.99799(12) 0.0790(7) Uani 1 1 d . . .
H15 H -0.2274 0.4739 1.0269 0.095 Uiso 1 1 calc R . .
C16 C 0.0075(5) 0.38857(14) 1.00669(11) 0.0737(6) Uani 1 1 d . . .
H16 H 0.1225 0.4023 1.0413 0.088 Uiso 1 1 calc R . .
C17 C 0.0466(4) 0.32494(12) 0.96414(10) 0.0630(5) Uani 1 1 d . . .
H17 H 0.1870 0.2958 0.9709 0.076 Uiso 1 1 calc R . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 N1 109.24(12) . . ?
C11 N1 C4 111.03(14) . . ?
C11 N1 O1 102.17(15) . . ?
C4 N1 O1 104.32(12) . . ?
O1 C1 C2 111.42(14) . . ?
O1 C1 C9 111.64(13) . . ?
C2 C1 C9 111.74(15) . . ?
O1 C1 H1 107.3 . . ?
C2 C1 H1 107.3 . . ?
C9 C1 H1 107.3 . . ?
C3 O2 C6 109.04(12) . . ?
O3 C2 C1 109.97(15) . . ?
O3 C2 C3 101.85(13) . . ?
C1 C2 C3 114.47(13) . . ?
O3 C2 H2 110.1 . . ?
C1 C2 H2 110.1 . . ?
C3 C2 H2 110.1 . . ?
O4 N2 O5 122.8(2) . . ?
O4 N2 C9 118.68(19) . . ?
O5 N2 C9 118.5(2) . . ?
C2 O3 C6 106.31(14) . . ?
O2 C3 C2 102.89(13) . . ?
O2 C3 C4 109.47(14) . . ?
C2 C3 C4 113.87(15) . . ?
O2 C3 H3 110.1 . . ?
C2 C3 H3 110.1 . . ?
C4 C3 H3 110.1 . . ?
N1 C4 C5 111.48(14) . . ?
N1 C4 C3 107.53(13) . . ?
C5 C4 C3 109.71(18) . . ?
N1 C4 H4 109.4 . . ?
C5 C4 H4 109.4 . . ?
C3 C4 H4 109.4 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O3 C6 O2 105.35(13) . . ?
O3 C6 C8 108.30(17) . . ?
O2 C6 C8 110.49(16) . . ?
O3 C6 C7 111.25(16) . . ?
O2 C6 C7 107.90(18) . . ?
C8 C6 C7 113.26(18) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C10 107.71(14) . . ?
N2 C9 C1 108.39(15) . . ?
C10 C9 C1 113.93(19) . . ?
N2 C9 H9 108.9 . . ?
C10 C9 H9 108.9 . . ?
C1 C9 H9 108.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 113.82(15) . . ?
N1 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
N1 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C17 118.5(2) . . ?
C13 C12 C11 121.9(2) . . ?
C17 C12 C11 119.5(2) . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 120.7(2) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 119.3(2) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 120.1(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 121.1(2) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
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
O1 C1 1.422(2) . ?
O1 N1 1.4799(18) . ?
N1 C11 1.476(2) . ?
N1 C4 1.479(2) . ?
C1 C2 1.517(2) . ?
C1 C9 1.530(3) . ?
C1 H1 0.9800 . ?
O2 C3 1.426(2) . ?
O2 C6 1.440(2) . ?
C2 O3 1.425(2) . ?
C2 C3 1.518(2) . ?
C2 H2 0.9800 . ?
N2 O4 1.198(3) . ?
N2 O5 1.212(3) . ?
N2 C9 1.511(2) . ?
O3 C6 1.429(2) . ?
C3 C4 1.525(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.522(3) . ?
C4 H4 0.9800 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C8 1.503(3) . ?
C6 C7 1.520(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.513(3) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.508(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.370(3) . ?
C12 C17 1.386(3) . ?
C13 C14 1.391(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.366(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 N1 C11 167.76(14) . . . . ?
C1 O1 N1 C4 -76.52(15) . . . . ?
N1 O1 C1 C2 60.32(17) . . . . ?
N1 O1 C1 C9 -65.39(17) . . . . ?
O1 C1 C2 O3 74.67(17) . . . . ?
C9 C1 C2 O3 -159.69(13) . . . . ?
O1 C1 C2 C3 -39.3(2) . . . . ?
C9 C1 C2 C3 86.39(18) . . . . ?
C1 C2 O3 C6 -159.69(13) . . . . ?
C3 C2 O3 C6 -37.92(16) . . . . ?
C6 O2 C3 C2 -18.60(19) . . . . ?
C6 O2 C3 C4 102.82(17) . . . . ?
O3 C2 C3 O2 34.24(17) . . . . ?
C1 C2 C3 O2 152.86(16) . . . . ?
O3 C2 C3 C4 -84.13(16) . . . . ?
C1 C2 C3 C4 34.5(2) . . . . ?
C11 N1 C4 C5 -62.2(2) . . . . ?
O1 N1 C4 C5 -171.54(16) . . . . ?
C11 N1 C4 C3 177.50(16) . . . . ?
O1 N1 C4 C3 68.16(17) . . . . ?
O2 C3 C4 N1 -164.13(14) . . . . ?
C2 C3 C4 N1 -49.60(19) . . . . ?
O2 C3 C4 C5 74.46(19) . . . . ?
C2 C3 C4 C5 -171.01(15) . . . . ?
C2 O3 C6 O2 27.10(17) . . . . ?
C2 O3 C6 C8 145.34(16) . . . . ?
C2 O3 C6 C7 -89.57(19) . . . . ?
C3 O2 C6 O3 -4.11(19) . . . . ?
C3 O2 C6 C8 -120.86(18) . . . . ?
C3 O2 C6 C7 114.82(18) . . . . ?
O4 N2 C9 C10 -75.6(3) . . . . ?
O5 N2 C9 C10 104.1(3) . . . . ?
O4 N2 C9 C1 48.1(3) . . . . ?
O5 N2 C9 C1 -132.2(2) . . . . ?
O1 C1 C9 N2 -165.80(14) . . . . ?
C2 C1 C9 N2 68.67(18) . . . . ?
O1 C1 C9 C10 -45.9(2) . . . . ?
C2 C1 C9 C10 -171.45(16) . . . . ?
C4 N1 C11 C12 -179.27(18) . . . . ?
O1 N1 C11 C12 -68.5(2) . . . . ?
N1 C11 C12 C13 94.0(2) . . . . ?
N1 C11 C12 C17 -88.7(2) . . . . ?
C17 C12 C13 C14 1.5(3) . . . . ?
C11 C12 C13 C14 178.7(2) . . . . ?
C12 C13 C14 C15 -1.3(4) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C14 C15 C16 C17 -0.7(3) . . . . ?
C15 C16 C17 C12 0.9(3) . . . . ?
C13 C12 C17 C16 -1.3(3) . . . . ?
C11 C12 C17 C16 -178.58(18) . . . . ?
