#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:21:33 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180134 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/32/7103270.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_7103270
loop_
_publ_author_name
'Kang, Jun Yong'
'Bugarin, Alejandro'
'Connell, Brian T'
_publ_section_title
;
 Conversion of nitrosobenzenes to isoxazolidines: an efficient cascade
 process utilizing reactive nitrone intermediates.
;
_journal_issue                   30
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3522
_journal_page_last               3524
_journal_paper_doi               10.1039/b806374e
_journal_year                    2008
_chemical_formula_sum            'C16 H17 N O'
_chemical_formula_weight         239.31
_chemical_name_systematic
;
?
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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            8
_cell_length_a                   15.772(8)
_cell_length_b                   6.743(4)
_cell_length_c                   24.033(13)
_cell_measurement_reflns_used    5156
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.58
_cell_volume                     2556(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_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  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            26298
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9810
_exptl_absorpt_correction_T_min  0.9698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0705
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1229P)²+0.7678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1715
_refine_ls_wR_factor_ref         0.1870
_reflns_number_gt                2386
_reflns_number_total             2941
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b806374e.txt
_cod_data_source_block           pbcn
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      Pbcn
_cod_database_code               7103270
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, 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
C1 C 0.87180(9) 0.2305(2) 0.62518(6) 0.0234(3) Uani 1 1 d . . .
C2 C 0.90531(10) 0.1415(2) 0.67294(7) 0.0274(4) Uani 1 1 d . . .
H2 H 0.9357 0.0203 0.6702 0.033 Uiso 1 1 calc R . .
C3 C 0.89385(10) 0.2311(3) 0.72431(7) 0.0302(4) Uani 1 1 d . . .
H3 H 0.9167 0.1707 0.7567 0.036 Uiso 1 1 calc R . .
C4 C 0.84917(10) 0.4089(3) 0.72912(6) 0.0303(4) Uani 1 1 d . . .
H4 H 0.8406 0.4677 0.7646 0.036 Uiso 1 1 calc R . .
C5 C 0.81731(10) 0.4993(3) 0.68155(6) 0.0283(4) Uani 1 1 d . . .
H5 H 0.7878 0.6216 0.6845 0.034 Uiso 1 1 calc R . .
C6 C 0.82830(9) 0.4123(2) 0.62969(6) 0.0249(3) Uani 1 1 d . . .
H6 H 0.8065 0.4751 0.5973 0.030 Uiso 1 1 calc R . .
C7 C 0.89433(10) -0.0723(2) 0.56915(7) 0.0260(4) Uani 1 1 d . . .
H7A H 0.8506 -0.1386 0.5921 0.031 Uiso 1 1 calc R . .
H7B H 0.9511 -0.1172 0.5813 0.031 Uiso 1 1 calc R . .
C8 C 0.88052(10) -0.1122(2) 0.50738(6) 0.0256(4) Uani 1 1 d . . .
H8A H 0.8496 -0.2382 0.5015 0.031 Uiso 1 1 calc R . .
H8B H 0.9352 -0.1177 0.4872 0.031 Uiso 1 1 calc R . .
C9 C 0.82633(9) 0.0689(2) 0.48802(6) 0.0233(3) Uani 1 1 d . . .
H9 H 0.7705 0.0193 0.4741 0.028 Uiso 1 1 calc R . .
C10 C 0.86840(9) 0.1879(2) 0.44225(6) 0.0224(3) Uani 1 1 d . . .
C11 C 0.86461(9) 0.1201(2) 0.38704(6) 0.0241(3) Uani 1 1 d . . .
C12 C 0.90539(9) 0.2311(2) 0.34579(6) 0.0262(4) Uani 1 1 d . . .
H12 H 0.9031 0.1868 0.3083 0.031 Uiso 1 1 calc R . .
C13 C 0.94940(10) 0.4049(2) 0.35826(7) 0.0278(4) Uani 1 1 d . . .
H13 H 0.9772 0.4772 0.3296 0.033 Uiso 1 1 calc R . .
C14 C 0.95218(10) 0.4712(2) 0.41281(6) 0.0263(4) Uani 1 1 d . . .
H14 H 0.9817 0.5898 0.4218 0.032 Uiso 1 1 calc R . .
C15 C 0.91151(9) 0.3632(2) 0.45457(6) 0.0238(3) Uani 1 1 d . . .
H15 H 0.9132 0.4097 0.4919 0.029 Uiso 1 1 calc R . .
C16 C 0.81529(11) -0.0647(2) 0.37169(7) 0.0314(4) Uani 1 1 d . . .
H16A H 0.8166 -0.0829 0.3312 0.047 Uiso 1 1 calc R . .
H16B H 0.7564 -0.0507 0.3841 0.047 Uiso 1 1 calc R . .
H16C H 0.8410 -0.1802 0.3898 0.047 Uiso 1 1 calc R . .
N1 N 0.88672(8) 0.14467(18) 0.57244(5) 0.0233(3) Uani 1 1 d . . .
O1 O 0.81204(6) 0.18574(15) 0.53726(4) 0.0240(3) Uani 1 1 d . . .
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
C2 C1 C6 119.61(14) . . ?
C2 C1 N1 119.82(14) . . ?
C6 C1 N1 120.44(13) . . ?
C3 C2 C1 119.62(15) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.94(15) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.43(15) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C6 C5 C4 120.52(16) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 119.85(14) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
N1 C7 C8 102.49(12) . . ?
N1 C7 H7A 111.3 . . ?
C8 C7 H7A 111.3 . . ?
N1 C7 H7B 111.3 . . ?
C8 C7 H7B 111.3 . . ?
H7A C7 H7B 109.2 . . ?
C7 C8 C9 103.32(12) . . ?
C7 C8 H8A 111.1 . . ?
C9 C8 H8A 111.1 . . ?
C7 C8 H8B 111.1 . . ?
C9 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
O1 C9 C10 112.07(12) . . ?
O1 C9 C8 105.60(12) . . ?
C10 C9 C8 113.01(12) . . ?
O1 C9 H9 108.7 . . ?
C10 C9 H9 108.7 . . ?
C8 C9 H9 108.7 . . ?
C15 C10 C11 119.80(14) . . ?
C15 C10 C9 120.54(13) . . ?
C11 C10 C9 119.66(14) . . ?
C12 C11 C10 118.41(14) . . ?
C12 C11 C16 120.25(14) . . ?
C10 C11 C16 121.31(14) . . ?
C13 C12 C11 121.75(14) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C14 C13 C12 119.33(14) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 119.84(14) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C10 C15 C14 120.86(14) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 N1 C7 118.00(12) . . ?
C1 N1 O1 107.70(11) . . ?
C7 N1 O1 102.77(11) . . ?
C9 O1 N1 104.09(10) . . ?
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
C1 C2 1.399(2) . ?
C1 C6 1.409(2) . ?
C1 N1 1.413(2) . ?
C2 C3 1.387(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.470(2) . ?
C7 C8 1.524(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.561(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O1 1.4392(18) . ?
C9 C10 1.515(2) . ?
C9 H9 1.0000 . ?
C10 C15 1.395(2) . ?
C10 C11 1.405(2) . ?
C11 C12 1.399(2) . ?
C11 C16 1.515(2) . ?
C12 C13 1.395(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.396(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N1 O1 1.4761(16) . ?
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
C6 C1 C2 C3 1.3(2) . . . . ?
N1 C1 C2 C3 177.02(14) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C2 C3 C4 C5 -1.4(2) . . . . ?
C3 C4 C5 C6 1.2(2) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C2 C1 C6 C5 -1.5(2) . . . . ?
N1 C1 C6 C5 -177.18(13) . . . . ?
N1 C7 C8 C9 -25.60(14) . . . . ?
C7 C8 C9 O1 -1.85(14) . . . . ?
C7 C8 C9 C10 120.99(13) . . . . ?
O1 C9 C10 C15 19.44(19) . . . . ?
C8 C9 C10 C15 -99.72(16) . . . . ?
O1 C9 C10 C11 -161.16(12) . . . . ?
C8 C9 C10 C11 79.68(17) . . . . ?
C15 C10 C11 C12 0.6(2) . . . . ?
C9 C10 C11 C12 -178.80(13) . . . . ?
C15 C10 C11 C16 -177.38(14) . . . . ?
C9 C10 C11 C16 3.2(2) . . . . ?
C10 C11 C12 C13 0.2(2) . . . . ?
C16 C11 C12 C13 178.23(14) . . . . ?
C11 C12 C13 C14 -0.7(2) . . . . ?
C12 C13 C14 C15 0.4(2) . . . . ?
C11 C10 C15 C14 -1.0(2) . . . . ?
C9 C10 C15 C14 178.44(13) . . . . ?
C13 C14 C15 C10 0.5(2) . . . . ?
C2 C1 N1 C7 32.35(19) . . . . ?
C6 C1 N1 C7 -151.96(14) . . . . ?
C2 C1 N1 O1 147.98(13) . . . . ?
C6 C1 N1 O1 -36.34(17) . . . . ?
C8 C7 N1 C1 162.13(12) . . . . ?
C8 C7 N1 O1 43.85(13) . . . . ?
C10 C9 O1 N1 -94.76(13) . . . . ?
C8 C9 O1 N1 28.69(13) . . . . ?
C1 N1 O1 C9 -171.42(11) . . . . ?
C7 N1 O1 C9 -46.13(13) . . . . ?
