#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009110.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_2009110
loop_
_publ_author_name
'Mukherjee, S.'
'Parmar, V. S.'
'Errington, W.'
_publ_section_title
;
 5-Acetoxy-2,3-diphenylisoxazolidine and
 5-acetoxy-3-(4-nitrophenyl)-2-phenylisoxazolidine
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1829
_journal_page_last               1831
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C17 H17 N O3'
_chemical_formula_weight         283.32
_chemical_name_systematic
;
 2,3-Diphenyl-5-acetoxyisoxazolidene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.054(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7637(13)
_cell_length_b                   13.9610(15)
_cell_length_c                   9.6642(10)
_cell_measurement_reflns_used    3395
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.38
_cell_volume                     1460.4(3)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1994)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL/PC (Sheldrick, 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
' Siemens SMART CCD area-detector diffractometer'
_diffrn_measurement_method       '\w scans'
_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  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0574
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7904
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.38
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9930
_exptl_absorpt_correction_T_min  0.9756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.195
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0505
_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/[\s^2^(Fo^2^)+(0.0609P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1230
_reflns_number_gt                1790
_reflns_number_total             2848
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    cf1330.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21 /c'
_cod_database_code               2009110
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O1 -0.00526(11) 0.15182(10) 0.75364(13) 0.0361(4) Uani d . 1 O
O2 0.12873(12) 0.18138(10) 0.63145(14) 0.0381(4) Uani d . 1 O
O3 0.28018(14) 0.19404(12) 0.86161(18) 0.0548(5) Uani d . 1 O
N2 -0.10865(13) 0.10730(12) 0.62731(16) 0.0312(4) Uani d . 1 N
C3 -0.17271(17) 0.18903(14) 0.5309(2) 0.0323(5) Uani d . 1 C
H3A -0.2325 0.2184 0.5688 0.039 Uiso calc R 1 H
C4 -0.06624(18) 0.25912(15) 0.5518(2) 0.0383(5) Uani d . 1 C
H4A -0.0463 0.2600 0.4613 0.046 Uiso calc R 1 H
H4B -0.0883 0.3248 0.5709 0.046 Uiso calc R 1 H
C5 0.04170(18) 0.22140(15) 0.6864(2) 0.0352(5) Uani d . 1 C
H5A 0.0810 0.2745 0.7589 0.042 Uiso calc R 1 H
C6 0.2471(2) 0.17418(15) 0.7307(3) 0.0404(5) Uani d . 1 C
C7 0.3282(2) 0.13879(19) 0.6555(3) 0.0582(7) Uani d . 1 C
H7A 0.4144 0.1397 0.7273 0.087 Uiso calc R 1 H
H7B 0.3188 0.1803 0.5698 0.087 Uiso calc R 1 H
H7C 0.3045 0.0732 0.6199 0.087 Uiso calc R 1 H
C1' -0.23970(17) 0.15554(15) 0.3702(2) 0.0311(5) Uani d . 1 C
C2' -0.35434(18) 0.19276(16) 0.2823(2) 0.0405(6) Uani d . 1 C
H2'A -0.3917 0.2387 0.3237 0.049 Uiso calc R 1 H
C3' -0.4153(2) 0.16348(18) 0.1339(2) 0.0495(6) Uani d . 1 C
H3'A -0.4934 0.1901 0.0739 0.059 Uiso calc R 1 H
C4' -0.3624(2) 0.09575(18) 0.0739(2) 0.0486(6) Uani d . 1 C
H4'A -0.4047 0.0746 -0.0268 0.058 Uiso calc R 1 H
C5' -0.2480(2) 0.05896(16) 0.1606(2) 0.0459(6) Uani d . 1 C
H5'A -0.2111 0.0128 0.1191 0.055 Uiso calc R 1 H
C6' -0.18653(19) 0.08872(15) 0.3078(2) 0.0387(5) Uani d . 1 C
H6'A -0.1073 0.0632 0.3664 0.046 Uiso calc R 1 H
C1" -0.17667(17) 0.05059(14) 0.6908(2) 0.0301(5) Uani d . 1 C
C2" -0.30489(18) 0.05062(15) 0.6321(2) 0.0370(5) Uani d . 1 C
H2"A -0.3499 0.0927 0.5521 0.044 Uiso calc R 1 H
C3" -0.36710(19) -0.01121(16) 0.6910(2) 0.0425(6) Uani d . 1 C
H3"A -0.4549 -0.0121 0.6492 0.051 Uiso calc R 1 H
C4" -0.30346(19) -0.07125(16) 0.8091(2) 0.0402(5) Uani d . 1 C
H4"A -0.3468 -0.1129 0.8492 0.048 Uiso calc R 1 H
C5" -0.17593(19) -0.07018(14) 0.8687(2) 0.0368(5) Uani d . 1 C
H5"A -0.1313 -0.1108 0.9510 0.044 Uiso calc R 1 H
C6" -0.11283(18) -0.01051(14) 0.8093(2) 0.0339(5) Uani d . 1 C
H6"A -0.0251 -0.0113 0.8498 0.041 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0365(8) 0.0425(9) 0.0260(7) -0.0080(7) 0.0089(6) -0.0013(6)
O2 0.0358(8) 0.0454(10) 0.0345(8) -0.0018(7) 0.0153(7) -0.0033(7)
O3 0.0515(10) 0.0580(12) 0.0438(10) 0.0031(8) 0.0065(8) 0.0005(8)
N2 0.0314(9) 0.0338(10) 0.0250(8) -0.0026(8) 0.0074(7) -0.0001(7)
C3 0.0363(11) 0.0324(12) 0.0308(11) 0.0039(9) 0.0158(9) 0.0023(9)
C4 0.0430(12) 0.0351(13) 0.0370(12) -0.0020(10) 0.0157(10) 0.0004(10)
C5 0.0416(12) 0.0347(13) 0.0327(11) -0.0052(10) 0.0183(10) -0.0038(10)
C6 0.0425(13) 0.0336(14) 0.0446(14) -0.0036(10) 0.0167(11) 0.0062(11)
C7 0.0516(14) 0.0577(18) 0.0734(17) 0.0070(13) 0.0333(13) 0.0106(14)
C1' 0.0325(11) 0.0323(12) 0.0293(11) -0.0026(9) 0.0131(9) 0.0027(9)
C2' 0.0393(12) 0.0479(15) 0.0357(12) 0.0032(11) 0.0163(10) 0.0045(11)
C3' 0.0377(12) 0.0701(18) 0.0372(13) -0.0038(12) 0.0107(11) 0.0114(12)
C4' 0.0580(15) 0.0570(17) 0.0292(12) -0.0203(13) 0.0153(11) -0.0049(11)
C5' 0.0649(16) 0.0400(14) 0.0374(12) -0.0046(12) 0.0250(12) -0.0038(11)
C6' 0.0445(12) 0.0391(13) 0.0325(11) 0.0010(10) 0.0150(10) 0.0005(10)
C1" 0.0374(11) 0.0302(12) 0.0238(10) -0.0024(9) 0.0130(9) -0.0039(9)
C2" 0.0397(12) 0.0413(14) 0.0292(11) -0.0003(10) 0.0126(9) 0.0022(10)
C3" 0.0372(12) 0.0528(15) 0.0378(12) -0.0049(11) 0.0151(10) 0.0009(11)
C4" 0.0493(13) 0.0382(14) 0.0389(12) -0.0069(10) 0.0235(11) -0.0020(10)
C5" 0.0481(13) 0.0279(12) 0.0349(11) 0.0026(10) 0.0170(10) 0.0024(10)
C6" 0.0358(11) 0.0319(12) 0.0343(11) 0.0010(9) 0.0140(9) -0.0010(10)
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
C5 O1 N2 104.77(12) y
C6 O2 C5 116.87(15) ?
C1" N2 C3 117.82(15) ?
C1" N2 O1 107.26(12) ?
C3 N2 O1 104.29(14) y
N2 C3 C1' 109.88(16) ?
N2 C3 C4 102.72(15) y
C1' C3 C4 113.61(15) ?
C5 C4 C3 104.91(16) y
O1 C5 O2 111.71(16) ?
O1 C5 C4 106.88(15) y
O2 C5 C4 107.28(15) ?
O3 C6 O2 123.35(19) ?
O3 C6 C7 125.7(2) ?
O2 C6 C7 110.91(19) ?
C2' C1' C6' 118.91(18) ?
C2' C1' C3 120.29(18) ?
C6' C1' C3 120.79(17) ?
C1' C2' C3' 120.5(2) ?
C4' C3' C2' 120.0(2) ?
C5' C4' C3' 119.6(2) ?
C4' C5' C6' 120.5(2) ?
C5' C6' C1' 120.4(2) ?
C2" C1" C6" 119.16(18) ?
C2" C1" N2 121.85(17) ?
C6" C1" N2 118.88(17) ?
C1" C2" C3" 119.65(19) ?
C4" C3" C2" 121.00(19) ?
C3" C4" C5" 119.21(19) ?
C4" C5" C6" 120.43(19) ?
C5" C6" C1" 120.52(18) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C5 1.397(2) y
O1 N2 1.4809(18) y
O2 C6 1.350(2) ?
O2 C5 1.438(2) y
O3 C6 1.202(2) ?
N2 C1" 1.424(2) y
N2 C3 1.479(2) y
C3 C1' 1.515(3) y
C3 C4 1.539(3) y
C4 C5 1.513(3) y
C6 C7 1.492(3) ?
C1' C2' 1.383(3) ?
C1' C6' 1.386(3) ?
C2' C3' 1.390(3) ?
C3' C4' 1.379(3) ?
C4' C5' 1.376(3) ?
C5' C6' 1.383(3) ?
C1" C2" 1.388(3) ?
C1" C6" 1.389(3) ?
C2" C3" 1.390(3) ?
C3" C4" 1.377(3) ?
C4" C5" 1.381(3) ?
C5" C6" 1.381(3) ?
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 O1 N2 C1" -167.77(15) ?
C5 O1 N2 C3 -42.08(17) y
C1" N2 C3 C1' -87.05(19) ?
O1 N2 C3 C1' 154.22(13) ?
C1" N2 C3 C4 151.74(15) ?
O1 N2 C3 C4 33.01(17) y
N2 C3 C4 C5 -13.67(19) y
C1' C3 C4 C5 -132.30(17) ?
N2 O1 C5 O2 -84.37(16) ?
N2 O1 C5 C4 32.69(18) y
C6 O2 C5 O1 -85.6(2) ?
C6 O2 C5 C4 157.59(16) ?
C3 C4 C5 O1 -11.7(2) y
C3 C4 C5 O2 108.22(17) ?
C5 O2 C6 O3 4.5(3) ?
C5 O2 C6 C7 -175.57(17) ?
N2 C3 C1' C2' 141.88(18) ?
C4 C3 C1' C2' -103.7(2) ?
N2 C3 C1' C6' -39.4(2) ?
C4 C3 C1' C6' 75.1(2) ?
C6' C1' C2' C3' 0.1(3) ?
C3 C1' C2' C3' 178.91(18) ?
C1' C2' C3' C4' 1.0(3) ?
C2' C3' C4' C5' -1.4(3) ?
C3' C4' C5' C6' 0.7(3) ?
C4' C5' C6' C1' 0.4(3) ?
C2' C1' C6' C5' -0.8(3) ?
C3 C1' C6' C5' -179.61(18) ?
C3 N2 C1" C2" 19.6(3) ?
O1 N2 C1" C2" 136.70(18) ?
C3 N2 C1" C6" -164.22(17) ?
O1 N2 C1" C6" -47.1(2) ?
C6" C1" C2" C3" -1.0(3) ?
N2 C1" C2" C3" 175.25(18) ?
C1" C2" C3" C4" 1.4(3) ?
C2" C3" C4" C5" -0.5(3) ?
C3" C4" C5" C6" -0.8(3) ?
C4" C5" C6" C1" 1.3(3) ?
C2" C1" C6" C5" -0.4(3) ?
N2 C1" C6" C5" -176.67(17) ?