#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:39:52 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180310 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/24/7152493.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_7152493
loop_
_publ_author_name
'Hashimoto, Yoshimitsu'
'Takada, Akiomi'
'Takikawa, Hiroshi'
'Suzuki, Keisuke'
_publ_section_title
;
 Synthesis of isoxazoles en route to semi-aromatized polyketides:
 dehydrogenation of benzonitrile oxide-para-quinone acetal cycloadducts.
;
_journal_issue                   30
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6003
_journal_page_last               6009
_journal_paper_doi               10.1039/c2ob25423a
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C13 H15 N O5'
_chemical_formula_sum            'C13 H15 N O5'
_chemical_formula_weight         265.26
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                   13.0620(11)
_cell_length_b                   12.0982(8)
_cell_length_c                   16.2166(13)
_cell_measurement_reflns_used    23309
_cell_measurement_temperature    169(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.12
_cell_volume                     2562.7(3)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-2004 (Burla, 2005)'
_diffrn_ambient_temperature      169(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Area Detector System'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23309
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.12
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9487
_exptl_absorpt_correction_T_min  0.9389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'absorption was corrected by ABSCOR'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2912
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0440
_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)+(0.0638P)²+0.5373P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1234
_reflns_number_gt                2304
_reflns_number_total             2912
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25423a.txt
_cod_data_source_block           shelxl_2c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' tag value 'orthorohmbic' was replaced with
'orthorhombic' value as specified in the replacement file
'/home/robertas/cod-tools/perl-scripts/inputs/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P bca'
_cod_database_code               7152493
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y-1/2, -z-1/2'
'x-1/2, y, -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 -0.06556(8) 0.16977(10) 0.71797(7) 0.0492(3) Uani 1 1 d .
O2 O 0.15926(12) 0.01815(13) 0.84921(8) 0.0709(4) Uani 1 1 d .
O3 O 0.21718(8) -0.06721(8) 0.60222(8) 0.0474(3) Uani 1 1 d .
O4 O 0.29643(7) 0.10216(8) 0.58227(7) 0.0420(3) Uani 1 1 d .
O5 O 0.12580(10) 0.11434(10) 0.41709(7) 0.0541(3) Uani 1 1 d .
N1 N 0.13277(10) 0.04342(10) 0.77843(8) 0.0416(3) Uani 1 1 d .
C1 C -0.02666(11) 0.15798(11) 0.64036(9) 0.0369(3) Uani 1 1 d .
C2 C 0.06846(10) 0.10289(10) 0.63579(8) 0.0312(3) Uani 1 1 d .
C3 C 0.11812(11) 0.08752(10) 0.56009(8) 0.0324(3) Uani 1 1 d .
C4 C 0.07170(12) 0.12879(11) 0.48870(9) 0.0377(3) Uani 1 1 d .
C5 C -0.02319(12) 0.18027(11) 0.49318(10) 0.0434(4) Uani 1 1 d .
H5 H -0.0551 0.2059 0.4441 0.052 Uiso 1 1 calc R
C6 C -0.07205(11) 0.19473(12) 0.56849(11) 0.0425(4) Uani 1 1 d .
H6 H -0.1370 0.2300 0.5706 0.051 Uiso 1 1 calc R
C7 C 0.11199(10) 0.06565(11) 0.71211(9) 0.0352(3) Uani 1 1 d .
C8 C 0.22000(11) 0.02966(11) 0.55417(9) 0.0348(3) Uani 1 1 d .
H8 H 0.2338 0.0097 0.4954 0.042 Uiso 1 1 calc R
C9 C 0.31196(13) -0.12697(13) 0.59442(13) 0.0548(5) Uani 1 1 d .
H9A H 0.3212 -0.1508 0.5365 0.066 Uiso 1 1 calc R
H9B H 0.3097 -0.1939 0.6295 0.066 Uiso 1 1 calc R
C10 C 0.39976(12) -0.05629(13) 0.61975(11) 0.0464(4) Uani 1 1 d .
H10A H 0.4650 -0.0948 0.6080 0.056 Uiso 1 1 calc R
H10B H 0.3963 -0.0416 0.6797 0.056 Uiso 1 1 calc R
C11 C 0.39577(12) 0.05120(14) 0.57292(14) 0.0567(5) Uani 1 1 d .
H11A H 0.4494 0.1018 0.5939 0.068 Uiso 1 1 calc R
H11B H 0.4094 0.0373 0.5138 0.068 Uiso 1 1 calc R
C12 C -0.16096(14) 0.22694(17) 0.72534(13) 0.0637(5) Uani 1 1 d .
H12A H -0.1547 0.3007 0.7008 0.076 Uiso 1 1 calc R
H12B H -0.1791 0.2340 0.7837 0.076 Uiso 1 1 calc R
H12C H -0.2145 0.1854 0.6965 0.076 Uiso 1 1 calc R
C13 C 0.08504(17) 0.16026(17) 0.34375(11) 0.0630(5) Uani 1 1 d .
H13A H 0.0151 0.1330 0.3355 0.076 Uiso 1 1 calc R
H13B H 0.1277 0.1385 0.2968 0.076 Uiso 1 1 calc R
H13C H 0.0840 0.2410 0.3483 0.076 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
C1 O1 C12 116.87(13)
C8 O3 C9 110.31(11)
C8 O4 C11 109.74(11)
C4 O5 C13 117.88(15)
C7 N1 O2 177.37(16)
O1 C1 C6 125.78(14)
O1 C1 C2 115.18(12)
C6 C1 C2 119.04(14)
C3 C2 C1 121.08(13)
C3 C2 C7 122.06(12)
C1 C2 C7 116.85(12)
C4 C3 C2 118.50(13)
C4 C3 C8 119.73(13)
C2 C3 C8 121.77(12)
O5 C4 C5 124.16(14)
O5 C4 C3 115.61(14)
C5 C4 C3 120.23(14)
C6 C5 C4 120.83(14)
C6 C5 H5 119.6
C4 C5 H5 119.6
C1 C6 C5 120.27(14)
C1 C6 H6 119.9
C5 C6 H6 119.9
N1 C7 C2 168.87(15)
O4 C8 O3 111.03(12)
O4 C8 C3 108.47(10)
O3 C8 C3 109.17(11)
O4 C8 H8 109.4
O3 C8 H8 109.4
C3 C8 H8 109.4
O3 C9 C10 110.48(12)
O3 C9 H9A 109.6
C10 C9 H9A 109.6
O3 C9 H9B 109.6
C10 C9 H9B 109.6
H9A C9 H9B 108.1
C9 C10 C11 109.27(14)
C9 C10 H10A 109.8
C11 C10 H10A 109.8
C9 C10 H10B 109.8
C11 C10 H10B 109.8
H10A C10 H10B 108.3
O4 C11 C10 110.27(13)
O4 C11 H11A 109.6
C10 C11 H11A 109.6
O4 C11 H11B 109.6
C10 C11 H11B 109.6
H11A C11 H11B 108.1
O1 C12 H12A 109.5
O1 C12 H12B 109.5
H12A C12 H12B 109.5
O1 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
O5 C13 H13A 109.5
O5 C13 H13B 109.5
H13A C13 H13B 109.5
O5 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3647(19)
O1 C12 1.4302(19)
O2 N1 1.2371(17)
O3 C8 1.4077(17)
O3 C9 1.4392(18)
O4 C8 1.4048(17)
O4 C11 1.4446(19)
O5 C4 1.3706(19)
O5 C13 1.416(2)
N1 C7 1.1415(18)
C1 C6 1.381(2)
C1 C2 1.4119(19)
C2 C3 1.4007(19)
C2 C7 1.435(2)
C3 C4 1.399(2)
C3 C8 1.5068(19)
C4 C5 1.389(2)
C5 C6 1.389(2)
C5 H5 0.9500
C6 H6 0.9500
C8 H8 1.0000
C9 C10 1.488(2)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.507(2)
C10 H10A 0.9900
C10 H10B 0.9900
C11 H11A 0.9900
C11 H11B 0.9900
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
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
C12 O1 C1 C6 -1.1(2)
C12 O1 C1 C2 178.90(13)
O1 C1 C2 C3 -178.49(12)
C6 C1 C2 C3 1.53(19)
O1 C1 C2 C7 0.43(17)
C6 C1 C2 C7 -179.55(12)
C1 C2 C3 C4 0.46(18)
C7 C2 C3 C4 -178.40(12)
C1 C2 C3 C8 179.55(12)
C7 C2 C3 C8 0.69(19)
C13 O5 C4 C5 3.7(2)
C13 O5 C4 C3 -176.41(13)
C2 C3 C4 O5 177.88(11)
C8 C3 C4 O5 -1.22(18)
C2 C3 C4 C5 -2.22(19)
C8 C3 C4 C5 178.68(12)
O5 C4 C5 C6 -178.11(13)
C3 C4 C5 C6 2.0(2)
O1 C1 C6 C5 178.24(13)
C2 C1 C6 C5 -1.8(2)
C4 C5 C6 C1 0.0(2)
O2 N1 C7 C2 -169(3)
C3 C2 C7 N1 178.5(7)
C1 C2 C7 N1 -0.4(8)
C11 O4 C8 O3 63.29(16)
C11 O4 C8 C3 -176.75(12)
C9 O3 C8 O4 -63.28(16)
C9 O3 C8 C3 177.18(13)
C4 C3 C8 O4 103.79(14)
C2 C3 C8 O4 -75.28(15)
C4 C3 C8 O3 -135.09(13)
C2 C3 C8 O3 45.83(16)
C8 O3 C9 C10 57.87(19)
O3 C9 C10 C11 -52.8(2)
C8 O4 C11 C10 -58.00(19)
C9 C10 C11 O4 53.0(2)
