#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009111.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_2009111
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 H16 N2 O5'
_chemical_formula_weight         328.32
_chemical_name_systematic
;
 2-phenyl-3-(4-nitrophenyl)-5-acetoxyisoxazolidine
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.842(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.9115(13)
_cell_length_b                   11.6279(13)
_cell_length_c                   7.7010(7)
_cell_measurement_reflns_used    2974
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.54
_cell_measurement_theta_min      2.09
_cell_volume                     1595.6(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 0.912
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device_type  ' Siemens SMART 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  0.0549
_diffrn_reflns_av_sigmaI/netI    0.0675
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4693
_diffrn_reflns_theta_full        28.54
_diffrn_reflns_theta_max         28.54
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9681
_exptl_absorpt_correction_T_min  0.9603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.185
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   1.9(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2388
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.911
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0431
_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/[\s^2^(Fo^2^)+(0.0442P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0977
_reflns_number_gt                1714
_reflns_number_total             2388
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    cf1330.cif
_[local]_cod_data_source_block   II
_[local]_cod_cif_authors_sg_H-M  Cc
_cod_database_code               2009111
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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 0.60658(12) 0.73686(16) 0.5439(3) 0.0393(5) Uani d . 1 O
O2 0.58414(10) 0.56527(16) 0.6939(2) 0.0394(5) Uani d . 1 O
O3 0.46880(12) 0.58005(19) 0.5493(3) 0.0554(6) Uani d . 1 O
O4 1.02155(15) 0.4889(3) 1.0266(4) 0.0922(10) Uani d . 1 O
O5 0.96400(16) 0.3468(2) 0.8875(4) 0.0757(8) Uani d . 1 O
N2 0.68700(13) 0.72061(19) 0.5441(3) 0.0326(5) Uani d . 1 N
N3 0.96892(17) 0.4486(3) 0.9318(4) 0.0573(8) Uani d . 1 N
C3 0.71957(16) 0.7439(2) 0.7266(3) 0.0335(6) Uani d . 1 C
H3 0.7348 0.8265 0.7387 0.040 Uiso calc R 1 H
C4 0.65347(18) 0.7202(3) 0.8349(4) 0.0477(8) Uani d . 1 C
H4A 0.6653 0.6557 0.9171 0.057 Uiso calc R 1 H
H4B 0.6415 0.7893 0.9020 0.057 Uiso calc R 1 H
C5 0.58912(16) 0.6897(2) 0.7015(4) 0.0393(7) Uani d . 1 C
H5 0.5412 0.7232 0.7354 0.047 Uiso calc R 1 H
C6 0.51913(18) 0.5210(3) 0.6178(4) 0.0401(7) Uani d . 1 C
C7 0.5166(2) 0.3929(2) 0.6325(5) 0.0569(9) Uani d . 1 C
H7A 0.4839 0.3615 0.5341 0.085 Uiso calc R 1 H
H7B 0.4969 0.3716 0.7422 0.085 Uiso calc R 1 H
H7C 0.5673 0.3616 0.6308 0.085 Uiso calc R 1 H
C1" 0.71369(16) 0.7949(2) 0.4150(3) 0.0313(6) Uani d . 1 C
C2" 0.79020(17) 0.7992(2) 0.4027(4) 0.0387(7) Uani d . 1 C
H2"A 0.8232 0.7552 0.4810 0.046 Uiso calc R 1 H
C3" 0.81917(19) 0.8666(2) 0.2782(4) 0.0437(7) Uani d . 1 C
H3"A 0.8718 0.8687 0.2709 0.052 Uiso calc R 1 H
C4" 0.77112(19) 0.9313(2) 0.1633(4) 0.0422(7) Uani d . 1 C
H4"A 0.7906 0.9773 0.0765 0.051 Uiso calc R 1 H
C5" 0.69573(18) 0.9280(2) 0.1764(4) 0.0421(8) Uani d . 1 C
H5"A 0.6632 0.9736 0.0995 0.051 Uiso calc R 1 H
C6" 0.66532(17) 0.8594(2) 0.2998(4) 0.0375(7) Uani d . 1 C
H6"A 0.6126 0.8566 0.3053 0.045 Uiso calc R 1 H
C1' 0.78694(15) 0.6671(2) 0.7752(3) 0.0305(6) Uani d . 1 C
C2' 0.78278(16) 0.5495(2) 0.7363(4) 0.0352(6) Uani d . 1 C
H2'A 0.7382 0.5186 0.6765 0.042 Uiso calc R 1 H
C3' 0.84288(17) 0.4784(2) 0.7841(4) 0.0391(7) Uani d . 1 C
H3'A 0.8405 0.3987 0.7571 0.047 Uiso calc R 1 H
C4' 0.90670(16) 0.5256(3) 0.8723(4) 0.0378(7) Uani d . 1 C
C5' 0.91287(17) 0.6412(2) 0.9109(4) 0.0422(7) Uani d . 1 C
H5'A 0.9575 0.6716 0.9707 0.051 Uiso calc R 1 H
C6' 0.85219(16) 0.7120(2) 0.8602(4) 0.0358(7) Uani d . 1 C
H6'A 0.8555 0.7921 0.8841 0.043 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 0.0336(12) 0.0395(11) 0.0444(11) 0.0035(9) 0.0025(9) 0.0066(9)
O2 0.0385(12) 0.0365(11) 0.0435(11) 0.0059(9) 0.0062(9) 0.0087(10)
O3 0.0436(14) 0.0585(15) 0.0629(15) 0.0013(12) -0.0011(11) 0.0070(12)
O4 0.0539(19) 0.081(2) 0.133(3) 0.0126(15) -0.0323(18) 0.0205(19)
O5 0.0797(19) 0.0495(16) 0.097(2) 0.0307(14) 0.0059(15) 0.0084(15)
N2 0.0309(13) 0.0319(12) 0.0340(12) 0.0044(10) -0.0008(10) 0.0001(10)
N3 0.0471(19) 0.0569(19) 0.068(2) 0.0184(15) 0.0065(16) 0.0208(17)
C3 0.0373(17) 0.0288(13) 0.0332(15) -0.0008(12) -0.0014(13) -0.0038(12)
C4 0.044(2) 0.0578(19) 0.0419(17) 0.0060(15) 0.0058(15) -0.0106(15)
C5 0.0378(18) 0.0379(16) 0.0431(17) 0.0067(14) 0.0087(13) -0.0009(14)
C6 0.0386(18) 0.0474(17) 0.0361(16) -0.0013(16) 0.0126(14) 0.0013(15)
C7 0.074(3) 0.0430(18) 0.057(2) -0.0079(18) 0.0220(18) -0.0023(17)
C1" 0.0395(17) 0.0244(13) 0.0298(14) 0.0001(11) 0.0022(12) -0.0046(11)
C2" 0.0424(18) 0.0350(16) 0.0390(16) 0.0081(13) 0.0053(13) 0.0014(14)
C3" 0.0433(18) 0.0417(17) 0.0475(18) 0.0014(14) 0.0120(14) -0.0007(15)
C4" 0.057(2) 0.0324(15) 0.0374(17) -0.0052(14) 0.0063(15) 0.0028(13)
C5" 0.057(2) 0.0288(15) 0.0384(18) 0.0008(14) -0.0036(15) 0.0048(13)
C6" 0.0384(17) 0.0311(15) 0.0414(16) -0.0019(13) -0.0035(12) 0.0005(13)
C1' 0.0370(16) 0.0257(13) 0.0287(14) 0.0018(12) 0.0026(12) 0.0037(11)
C2' 0.0383(17) 0.0307(14) 0.0352(15) -0.0030(13) -0.0023(12) -0.0006(12)
C3' 0.049(2) 0.0278(15) 0.0412(16) 0.0046(14) 0.0077(14) -0.0011(13)
C4' 0.0365(17) 0.0411(16) 0.0359(15) 0.0082(14) 0.0032(12) 0.0109(14)
C5' 0.0373(18) 0.0419(18) 0.0453(18) -0.0039(15) -0.0059(13) 0.0020(15)
C6' 0.0377(17) 0.0298(14) 0.0392(16) -0.0031(13) 0.0005(13) 0.0006(12)
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 104.9(2) y
C6 O2 C5 116.4(2) ?
C1" N2 O1 108.72(19) ?
C1" N2 C3 114.7(2) ?
O1 N2 C3 105.68(19) y
O4 N3 O5 124.2(3) y
O4 N3 C4' 117.8(3) ?
O5 N3 C4' 118.0(3) ?
N2 C3 C1' 110.5(2) ?
N2 C3 C4 103.3(2) y
C1' C3 C4 113.4(2) ?
C5 C4 C3 104.5(2) y
O1 C5 O2 112.0(2) ?
O1 C5 C4 106.1(2) y
O2 C5 C4 107.6(2) ?
O3 C6 O2 122.9(3) ?
O3 C6 C7 124.8(3) ?
O2 C6 C7 112.2(3) ?
C2" C1" C6" 119.5(2) ?
C2" C1" N2 118.1(2) ?
C6" C1" N2 122.4(2) ?
C3" C2" C1" 120.9(3) ?
C2" C3" C4" 119.8(3) ?
C5" C4" C3" 119.4(3) ?
C4" C5" C6" 121.7(3) ?
C5" C6" C1" 118.8(3) ?
C6' C1' C2' 119.6(3) ?
C6' C1' C3 120.4(2) ?
C2' C1' C3 119.9(2) ?
C3' C2' C1' 120.4(3) ?
C2' C3' C4' 118.5(3) ?
C5' C4' C3' 122.5(3) ?
C5' C4' N3 119.1(3) ?
C3' C4' N3 118.3(3) ?
C4' C5' C6' 118.3(3) ?
C1' C6' C5' 120.6(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C5 1.397(3) y
O1 N2 1.453(3) y
O2 C6 1.351(4) ?
O2 C5 1.451(3) ?
O3 C6 1.210(4) ?
O4 N3 1.225(4) y
O5 N3 1.233(4) y
N2 C1" 1.435(3) ?
N2 C3 1.491(3) y
N3 C4' 1.467(4) ?
C3 C1' 1.517(4) ?
C3 C4 1.541(4) y
C4 C5 1.506(4) y
C6 C7 1.495(4) ?
C1" C2" 1.384(4) ?
C1" C6" 1.394(4) ?
C2" C3" 1.379(4) ?
C3" C4" 1.391(4) ?
C4" C5" 1.365(4) ?
C5" C6" 1.393(4) ?
C1' C6' 1.383(4) ?
C1' C2' 1.399(4) ?
C2' C3' 1.378(4) ?
C3' C4' 1.383(4) ?
C4' C5' 1.378(4) ?
C5' C6' 1.388(4) ?
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" -163.11(19) ?
C5 O1 N2 C3 -39.5(2) y
C1" N2 C3 C1' -94.5(3) ?
O1 N2 C3 C1' 145.8(2) ?
C1" N2 C3 C4 144.0(2) ?
O1 N2 C3 C4 24.2(3) y
N2 C3 C4 C5 -1.9(3) y
C1' C3 C4 C5 -121.5(3) ?
N2 O1 C5 O2 -79.1(3) ?
N2 O1 C5 C4 38.0(2) y
C6 O2 C5 O1 -80.7(3) ?
C6 O2 C5 C4 163.1(2) ?
C3 C4 C5 O1 -22.0(3) y
C3 C4 C5 O2 98.0(2) ?
C5 O2 C6 O3 4.5(4) ?
C5 O2 C6 C7 -174.2(2) ?
O1 N2 C1" C2" 175.3(2) ?
C3 N2 C1" C2" 57.2(3) ?
O1 N2 C1" C6" -6.7(3) ?
C3 N2 C1" C6" -124.7(3) ?
C6" C1" C2" C3" 0.1(4) ?
N2 C1" C2" C3" 178.2(2) ?
C1" C2" C3" C4" 0.1(4) ?
C2" C3" C4" C5" 0.5(4) ?
C3" C4" C5" C6" -1.4(4) ?
C4" C5" C6" C1" 1.6(4) ?
C2" C1" C6" C5" -0.9(4) ?
N2 C1" C6" C5" -178.9(2) ?
N2 C3 C1' C6' 134.8(2) ?
C4 C3 C1' C6' -109.9(3) ?
N2 C3 C1' C2' -46.3(3) ?
C4 C3 C1' C2' 69.1(3) ?
C6' C1' C2' C3' 0.8(4) ?
C3 C1' C2' C3' -178.2(2) ?
C1' C2' C3' C4' 0.6(4) ?
C2' C3' C4' C5' -1.3(4) ?
C2' C3' C4' N3 176.5(2) ?
O4 N3 C4' C5' 6.0(4) ?
O5 N3 C4' C5' -176.0(3) ?
O4 N3 C4' C3' -171.9(3) ?
O5 N3 C4' C3' 6.1(4) ?
C3' C4' C5' C6' 0.6(4) ?
N3 C4' C5' C6' -177.2(3) ?
C2' C1' C6' C5' -1.5(4) ?
C3 C1' C6' C5' 177.4(3) ?
C4' C5' C6' C1' 0.8(4) ?