#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:21:33 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180134 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/32/7103269.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_7103269
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            'C23 H23 N O'
_chemical_formula_weight         329.42
_chemical_name_systematic
;
?
;
_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'
_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                 115.235(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.227(7)
_cell_length_b                   32.76(2)
_cell_length_c                   5.358(3)
_cell_measurement_reflns_used    1151
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.58
_cell_volume                     1782(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      140(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0714
_diffrn_reflns_av_sigmaI/netI    0.0835
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            8387
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9978
_exptl_absorpt_correction_T_min  0.9817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(2)
_refine_ls_extinction_coef       0.0133(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3136
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0548
_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
[0.00000+1.00000exp(1.00(sinθ/λ)²)]/
[σ²(Fo²)+0.0000+0.0000*P+(0.0633P)²+0.0000sinθ/λ]
where P = 0.33333Fo² + 0.66667Fc²
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1358
_reflns_number_gt                2124
_reflns_number_total             3136
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b806374e.txt
_cod_data_source_block           ccn
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      Cc
_cod_database_code               7103269
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_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 0.2185(4) 0.18952(10) 0.9957(7) 0.0343(9) Uani 1 1 d . . .
H1 H 0.3060 0.1854 1.1557 0.041 Uiso 1 1 calc R . .
C2 C 0.1127(4) 0.16421(11) 1.0297(7) 0.0383(9) Uani 1 1 d . . .
H2A H 0.0237 0.1746 0.9100 0.046 Uiso 1 1 calc R . .
H2B H 0.1247 0.1644 1.2238 0.046 Uiso 1 1 calc R . .
C3 C 0.1329(3) 0.12118(11) 0.9418(7) 0.0355(9) Uani 1 1 d . . .
H3 H 0.1952 0.1056 1.1061 0.043 Uiso 1 1 calc R . .
C4 C 0.0070(4) 0.09757(11) 0.7994(8) 0.0376(9) Uani 1 1 d . . .
C5 C -0.0843(4) 0.10982(13) 0.5373(9) 0.0495(10) Uani 1 1 d . . .
H5 H -0.0637 0.1329 0.4553 0.059 Uiso 1 1 calc R . .
C6 C -0.2019(5) 0.09032(15) 0.3925(10) 0.0618(12) Uani 1 1 d . . .
H6 H -0.2597 0.0990 0.2119 0.074 Uiso 1 1 calc R . .
C7 C -0.2337(4) 0.05838(14) 0.5127(10) 0.0578(12) Uani 1 1 d . . .
H7 H -0.3160 0.0451 0.4167 0.069 Uiso 1 1 calc R . .
C8 C -0.1503(4) 0.04489(12) 0.7684(10) 0.0538(12) Uani 1 1 d . . .
H8 H -0.1752 0.0221 0.8456 0.065 Uiso 1 1 calc R . .
C9 C -0.0261(4) 0.06420(11) 0.9231(8) 0.0467(10) Uani 1 1 d . . .
C10 C 0.0615(5) 0.04825(14) 1.1940(10) 0.0635(13) Uani 1 1 d . . .
H10A H 0.1436 0.0388 1.1903 0.095 Uiso 1 1 calc R . .
H10B H 0.0187 0.0254 1.2412 0.095 Uiso 1 1 calc R . .
H10C H 0.0811 0.0698 1.3326 0.095 Uiso 1 1 calc R . .
C11 C 0.1873(3) 0.23451(11) 0.9450(7) 0.0341(9) Uani 1 1 d . . .
C12 C 0.0971(4) 0.24710(11) 0.6832(8) 0.0383(9) Uani 1 1 d . . .
H12 H 0.0592 0.2277 0.5391 0.046 Uiso 1 1 calc R . .
C13 C 0.0630(4) 0.28788(12) 0.6335(8) 0.0416(9) Uani 1 1 d . . .
H13 H 0.0023 0.2964 0.4548 0.050 Uiso 1 1 calc R . .
C14 C 0.1163(4) 0.31610(12) 0.8411(8) 0.0431(10) Uani 1 1 d . . .
H14 H 0.0921 0.3440 0.8068 0.052 Uiso 1 1 calc R . .
C15 C 0.2056(4) 0.30367(12) 1.1007(8) 0.0426(10) Uani 1 1 d . . .
H15 H 0.2427 0.3235 1.2427 0.051 Uiso 1 1 calc R . .
C16 C 0.2425(4) 0.26279(11) 1.1598(7) 0.0369(9) Uani 1 1 d . . .
C17 C 0.3393(4) 0.25070(12) 1.4426(7) 0.0444(10) Uani 1 1 d . . .
H17A H 0.3543 0.2738 1.5691 0.067 Uiso 1 1 calc R . .
H17B H 0.4226 0.2429 1.4381 0.067 Uiso 1 1 calc R . .
H17C H 0.3044 0.2275 1.5063 0.067 Uiso 1 1 calc R . .
C18 C 0.3055(3) 0.10544(11) 0.7775(7) 0.0334(8) Uani 1 1 d . . .
C19 C 0.3129(4) 0.06458(12) 0.8566(8) 0.0440(10) Uani 1 1 d . . .
H19 H 0.2489 0.0536 0.9100 0.053 Uiso 1 1 calc R . .
C20 C 0.4127(4) 0.04032(12) 0.8571(8) 0.0468(10) Uani 1 1 d . . .
H20 H 0.4162 0.0124 0.9076 0.056 Uiso 1 1 calc R . .
C21 C 0.5090(4) 0.05603(12) 0.7847(8) 0.0465(10) Uani 1 1 d . . .
H21 H 0.5793 0.0393 0.7905 0.056 Uiso 1 1 calc R . .
C22 C 0.5005(4) 0.09618(12) 0.7047(8) 0.0432(10) Uani 1 1 d . . .
H22 H 0.5651 0.1070 0.6526 0.052 Uiso 1 1 calc R . .
C23 C 0.4000(3) 0.12118(12) 0.6982(7) 0.0378(9) Uani 1 1 d . . .
H23 H 0.3952 0.1488 0.6405 0.045 Uiso 1 1 calc R . .
N1 N 0.1953(3) 0.12908(9) 0.7496(6) 0.0372(8) Uani 1 1 d . . .
O1 O 0.2182(2) 0.17236(7) 0.7452(4) 0.0378(6) 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
O1 C1 C11 107.6(3) . . ?
O1 C1 C2 101.8(3) . . ?
C11 C1 C2 114.8(3) . . ?
O1 C1 H1 110.7 . . ?
C11 C1 H1 110.7 . . ?
C2 C1 H1 110.7 . . ?
C1 C2 C3 103.8(3) . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
C3 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
N1 C3 C4 110.8(3) . . ?
N1 C3 C2 103.1(3) . . ?
C4 C3 C2 113.5(3) . . ?
N1 C3 H3 109.7 . . ?
C4 C3 H3 109.7 . . ?
C2 C3 H3 109.7 . . ?
C5 C4 C9 117.9(4) . . ?
C5 C4 C3 119.3(3) . . ?
C9 C4 C3 122.7(3) . . ?
C6 C5 C4 123.4(4) . . ?
C6 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
C7 C6 C5 118.4(5) . . ?
C7 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C6 C7 C8 121.5(4) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C7 C8 C9 121.4(4) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C4 C9 C8 117.3(4) . . ?
C4 C9 C10 123.0(4) . . ?
C8 C9 C10 119.7(4) . . ?
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 . . ?
C12 C11 C16 120.5(3) . . ?
C12 C11 C1 118.8(3) . . ?
C16 C11 C1 120.7(3) . . ?
C13 C12 C11 120.0(4) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 120.4(4) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.7(4) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 121.8(4) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C15 C16 C11 117.6(3) . . ?
C15 C16 C17 120.1(3) . . ?
C11 C16 C17 122.3(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 119.4(3) . . ?
C19 C18 N1 119.6(3) . . ?
C23 C18 N1 120.6(3) . . ?
C20 C19 C18 119.9(4) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 121.0(4) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C22 C21 C20 118.8(3) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C21 C22 C23 121.5(4) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 H22 119.2 . . ?
C22 C23 C18 119.4(4) . . ?
C22 C23 H23 120.3 . . ?
C18 C23 H23 120.3 . . ?
C18 N1 O1 112.7(3) . . ?
C18 N1 C3 118.6(3) . . ?
O1 N1 C3 108.7(2) . . ?
N1 O1 C1 107.2(2) . . ?
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 O1 1.453(4) . ?
C1 C11 1.512(5) . ?
C1 C2 1.522(5) . ?
C1 H1 1.0000 . ?
C2 C3 1.534(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N1 1.494(4) . ?
C3 C4 1.503(5) . ?
C3 H3 1.0000 . ?
C4 C5 1.399(6) . ?
C4 C9 1.408(5) . ?
C5 C6 1.371(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.354(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.362(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.430(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.460(6) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.397(5) . ?
C11 C16 1.399(5) . ?
C12 C13 1.384(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.372(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.398(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.493(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.396(5) . ?
C18 C23 1.400(5) . ?
C18 N1 1.412(4) . ?
C19 C20 1.373(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.394(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.374(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.383(5) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
N1 O1 1.443(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 38.3(3) . . . . ?
C11 C1 C2 C3 154.2(3) . . . . ?
C1 C2 C3 N1 -26.0(3) . . . . ?
C1 C2 C3 C4 -145.9(3) . . . . ?
N1 C3 C4 C5 -46.8(4) . . . . ?
C2 C3 C4 C5 68.6(4) . . . . ?
N1 C3 C4 C9 135.6(3) . . . . ?
C2 C3 C4 C9 -108.9(4) . . . . ?
C9 C4 C5 C6 -2.0(6) . . . . ?
C3 C4 C5 C6 -179.7(4) . . . . ?
C4 C5 C6 C7 2.4(6) . . . . ?
C5 C6 C7 C8 -1.8(6) . . . . ?
C6 C7 C8 C9 0.9(6) . . . . ?
C5 C4 C9 C8 1.0(5) . . . . ?
C3 C4 C9 C8 178.6(3) . . . . ?
C5 C4 C9 C10 179.2(4) . . . . ?
C3 C4 C9 C10 -3.3(5) . . . . ?
C7 C8 C9 C4 -0.5(5) . . . . ?
C7 C8 C9 C10 -178.7(4) . . . . ?
O1 C1 C11 C12 36.2(4) . . . . ?
C2 C1 C11 C12 -76.3(4) . . . . ?
O1 C1 C11 C16 -146.9(3) . . . . ?
C2 C1 C11 C16 100.6(4) . . . . ?
C16 C11 C12 C13 0.8(5) . . . . ?
C1 C11 C12 C13 177.7(3) . . . . ?
C11 C12 C13 C14 -0.6(6) . . . . ?
C12 C13 C14 C15 0.6(5) . . . . ?
C13 C14 C15 C16 -0.7(6) . . . . ?
C14 C15 C16 C11 0.8(5) . . . . ?
C14 C15 C16 C17 179.9(3) . . . . ?
C12 C11 C16 C15 -0.9(5) . . . . ?
C1 C11 C16 C15 -177.7(3) . . . . ?
C12 C11 C16 C17 -179.9(4) . . . . ?
C1 C11 C16 C17 3.2(5) . . . . ?
C23 C18 C19 C20 0.3(6) . . . . ?
N1 C18 C19 C20 173.4(3) . . . . ?
C18 C19 C20 C21 1.3(6) . . . . ?
C19 C20 C21 C22 -1.8(6) . . . . ?
C20 C21 C22 C23 0.8(6) . . . . ?
C21 C22 C23 C18 0.6(6) . . . . ?
C19 C18 C23 C22 -1.2(5) . . . . ?
N1 C18 C23 C22 -174.3(3) . . . . ?
C19 C18 N1 O1 163.4(3) . . . . ?
C23 C18 N1 O1 -23.6(4) . . . . ?
C19 C18 N1 C3 34.8(5) . . . . ?
C23 C18 N1 C3 -152.2(3) . . . . ?
C4 C3 N1 C18 -103.6(3) . . . . ?
C2 C3 N1 C18 134.6(3) . . . . ?
C4 C3 N1 O1 125.9(3) . . . . ?
C2 C3 N1 O1 4.1(3) . . . . ?
C18 N1 O1 C1 -112.9(3) . . . . ?
C3 N1 O1 C1 20.7(3) . . . . ?
C11 C1 O1 N1 -157.5(2) . . . . ?
C2 C1 O1 N1 -36.5(3) . . . . ?
