#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:19:53 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180500 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/69/7216940.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_7216940
loop_
_publ_author_name
'Heaney, Frances'
'Rooney, Oliver'
'Cunningham, Desmond'
'McArdle, Patrick'
_publ_section_title
;
 Simultaneous double 1,3-dipolar cycloaddition reactions involving
 bisnitrones or bisdipolarophiles. 1H NMR investigation of the
 conformational preferences of N-methyl- and N-phenyl-isoxazolidines
;
_journal_issue                   3
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              373
_journal_paper_doi               10.1039/b007164l
_journal_year                    2001
_chemical_formula_sum            'C13 H14 N2 O3'
_chemical_formula_weight         246.26
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(9)
_cell_angle_beta                 97.595(11)
_cell_angle_gamma                90.000(13)
_cell_formula_units_Z            4
_cell_length_a                   11.858(2)
_cell_length_b                   7.7841(11)
_cell_length_c                   13.3660(11)
_cell_measurement_temperature    293(2)
_cell_volume                     1222.9(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.777
_diffrn_measured_fraction_theta_max 0.777
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2519
_diffrn_reflns_theta_full        27.97
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.096
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0867P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1411
_reflns_number_gt                1455
_reflns_number_total             2286
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b007164l.txt
_cod_data_source_block           or1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 
;
_cod_database_code               7216940
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, -z-1/2'
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
O1 O 0.11999(13) -0.20563(19) 0.46049(11) 0.0652(4) Uani 1 1 d .
O2 O 0.38844(13) 0.1398(2) 0.35388(12) 0.0701(5) Uani 1 1 d .
O3 O 0.15309(11) 0.25259(16) 0.26734(9) 0.0539(4) Uani 1 1 d .
N1 N 0.08262(13) 0.2501(2) 0.35141(11) 0.0483(4) Uani 1 1 d .
N2 N 0.27411(13) -0.0546(2) 0.42117(12) 0.0528(4) Uani 1 1 d .
C1 C -0.08440(17) 0.1154(2) 0.24061(14) 0.0526(5) Uani 1 1 d .
C2 C -0.0708(2) 0.0894(3) 0.14027(16) 0.0743(7) Uani 1 1 d .
H2 H -0.0010 0.0528 0.1236 0.097 Uiso 1 1 calc R
C3 C -0.1604(4) 0.1176(4) 0.0649(2) 0.1027(10) Uani 1 1 d .
H3 H -0.1504 0.0999 -0.0022 0.133 Uiso 1 1 calc R
C4 C -0.2633(3) 0.1712(4) 0.0881(3) 0.1038(11) Uani 1 1 d .
H4 H -0.3230 0.1903 0.0368 0.135 Uiso 1 1 calc R
C5 C -0.2790(2) 0.1969(3) 0.1866(2) 0.0884(9) Uani 1 1 d .
H5 H -0.3494 0.2327 0.2024 0.115 Uiso 1 1 calc R
C6 C -0.18965(19) 0.1693(3) 0.26234(18) 0.0685(6) Uani 1 1 d .
H6 H -0.2005 0.1874 0.3292 0.089 Uiso 1 1 calc R
C7 C 0.01146(16) 0.0951(2) 0.32593(13) 0.0460(4) Uani 1 1 d .
H7 H -0.0209 0.0591 0.3864 0.060 Uiso 1 1 calc R
C8 C 0.02289(18) 0.4133(3) 0.34576(17) 0.0624(6) Uani 1 1 d .
H8A H -0.0113 0.4334 0.2776 0.087 Uiso 1 1 calc R
H8B H 0.0757 0.5040 0.3666 0.087 Uiso 1 1 calc R
H8C H -0.0353 0.4105 0.3894 0.087 Uiso 1 1 calc R
C9 C 0.10474(15) -0.0320(2) 0.30790(12) 0.0476(5) Uani 1 1 d .
H9 H 0.0770 -0.1199 0.2581 0.062 Uiso 1 1 calc R
C10 C 0.19605(17) 0.0822(2) 0.27095(14) 0.0500(5) Uani 1 1 d .
H10 H 0.2133 0.0451 0.2046 0.065 Uiso 1 1 calc R
C11 C 0.29910(18) 0.0638(3) 0.35056(15) 0.0532(5) Uani 1 1 d .
C12 C 0.16236(17) -0.1100(2) 0.40468(14) 0.0500(5) Uani 1 1 d .
C13 C 0.3555(2) -0.1079(3) 0.50625(18) 0.0755(7) Uani 1 1 d .
H13A H 0.3605 -0.0213 0.5578 0.106 Uiso 1 1 calc R
H13B H 0.4288 -0.1233 0.4845 0.106 Uiso 1 1 calc R
H13C H 0.3311 -0.2142 0.5327 0.106 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
C10 O3 N1 101.38(12)
C8 N1 C7 116.12(15)
C8 N1 O3 105.58(14)
C7 N1 O3 101.32(12)
C11 N2 C12 112.80(17)
C11 N2 C13 123.12(18)
C12 N2 C13 124.01(17)
C6 C1 C2 118.07(19)
C6 C1 C7 118.92(17)
C2 C1 C7 122.94(19)
C3 C2 C1 120.4(3)
C4 C3 C2 120.6(3)
C3 C4 C5 120.2(3)
C4 C5 C6 119.6(3)
C5 C6 C1 121.3(2)
N1 C7 C1 115.90(15)
N1 C7 C9 99.27(14)
C1 C7 C9 115.96(15)
C12 C9 C7 112.40(14)
C12 C9 C10 104.52(15)
C7 C9 C10 103.45(14)
O3 C10 C11 111.36(15)
O3 C10 C9 106.70(14)
C11 C10 C9 104.89(14)
O2 C11 N2 124.6(2)
O2 C11 C10 126.87(18)
N2 C11 C10 108.49(17)
O1 C12 N2 124.14(18)
O1 C12 C9 126.79(19)
N2 C12 C9 109.07(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C12 1.209(2)
O2 C11 1.209(2)
O3 C10 1.419(2)
O3 N1 1.4864(19)
N1 C8 1.452(2)
N1 C7 1.486(2)
N2 C11 1.379(3)
N2 C12 1.383(3)
N2 C13 1.451(3)
C1 C6 1.383(3)
C1 C2 1.387(3)
C1 C7 1.508(3)
C2 C3 1.381(4)
C3 C4 1.363(5)
C4 C5 1.369(5)
C5 C6 1.383(3)
C7 C9 1.527(3)
C9 C12 1.508(3)
C9 C10 1.532(3)
C10 C11 1.517(3)
