#------------------------------------------------------------------------------
#$Date: 2022-04-22 18:35:43 +0300 (Fri, 22 Apr 2022) $
#$Revision: 274634 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/43/7204304.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_7204304
loop_
_publ_author_name
'Zhang, Yan'
'Xue, Jie'
'Gao, Yi'
'Fun, Hoong-Kun'
'Xu, Jian-Hua'
_publ_section_title
;
 Photoinduced [2+2] cycloadditions (the Paterno--Büchi reaction) of
 1-acetylisatin with enol ethers---regioselectivity, diastereoselectivity
 and acid catalysed transformations of the spirooxetane products
;
_journal_coden_ASTM              JCSPCE
_journal_issue                   3
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              345
_journal_page_last               353
_journal_paper_doi               10.1039/b109697d
_journal_year                    2002
_chemical_formula_sum            'C16 H19 N O4'
_chemical_formula_weight         289.32
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.046(2)
_cell_angle_beta                 105.633(2)
_cell_angle_gamma                101.122(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2141(8)
_cell_length_b                   8.7676(8)
_cell_length_c                   12.0117(11)
_cell_measurement_reflns_used    1749
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      1.85
_cell_volume                     776.65(13)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type
;
Siemens SMART CCD area detector diffractometer
;
_diffrn_measurement_method       'ω 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  0.0560
_diffrn_reflns_av_sigmaI/netI    0.1095
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4387
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.85
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.051(12)
_refine_ls_extinction_expression Fc^*^==kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2676
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.1514
_refine_ls_R_factor_gt           0.0835
_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)+(0.1397P)²+0.0000P] where P==(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2189
_refine_ls_wR_factor_ref         0.2592
_reflns_number_gt                1305
_reflns_number_total             2676
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            b109697d.txt
_cod_data_source_block           compound17
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7204304
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
O1 O -0.1696(4) 0.3746(4) 0.5150(3) 0.0809(10) Uani 1 1 d . . .
O2 O 0.2658(5) 0.1886(5) 0.5929(3) 0.0929(12) Uani 1 1 d . . .
O3 O 0.2406(4) -0.0576(3) 0.3702(3) 0.0755(10) Uani 1 1 d . . .
O4 O 0.3586(3) 0.2288(4) 0.2601(3) 0.0648(9) Uani 1 1 d . . .
N1 N 0.0134(4) 0.2257(4) 0.4671(3) 0.0534(9) Uani 1 1 d . . .
C1 C 0.0208(5) 0.0808(5) 0.2814(4) 0.0540(11) Uani 1 1 d . . .
C2 C -0.0442(6) 0.0022(6) 0.1564(4) 0.0706(13) Uani 1 1 d . . .
H2A H 0.0186 -0.0577 0.1183 0.085 Uiso 1 1 calc R . .
C3 C -0.2041(6) 0.0153(6) 0.0903(4) 0.0847(15) Uani 1 1 d . . .
H3A H -0.2488 -0.0337 0.0064 0.102 Uiso 1 1 calc R . .
C4 C -0.2978(6) 0.1011(7) 0.1488(5) 0.0829(15) Uani 1 1 d . . .
H4A H -0.4056 0.1077 0.1029 0.099 Uiso 1 1 calc R . .
C5 C -0.2378(5) 0.1765(5) 0.2715(4) 0.0664(13) Uani 1 1 d . . .
H5A H -0.3028 0.2338 0.3091 0.080 Uiso 1 1 calc R . .
C6 C -0.0763(5) 0.1648(5) 0.3385(4) 0.0504(10) Uani 1 1 d . . .
C7 C -0.0378(6) 0.3307(5) 0.5517(4) 0.0611(12) Uani 1 1 d . . .
C8 C 0.0724(6) 0.3860(6) 0.6821(4) 0.0817(14) Uani 1 1 d . . .
H8A H 0.1687 0.3378 0.6915 0.122 Uiso 1 1 calc R . .
H8B H 0.0025 0.3530 0.7290 0.122 Uiso 1 1 calc R . .
H8C H 0.1173 0.5030 0.7099 0.122 Uiso 1 1 calc R . .
C9 C 0.1668(5) 0.1720(5) 0.4934(4) 0.0582(11) Uani 1 1 d . . .
C10 C 0.1886(5) 0.0905(5) 0.3729(4) 0.0543(11) Uani 1 1 d . . .
C11 C 0.3927(6) 0.0006(6) 0.3373(5) 0.0814(15) Uani 1 1 d . . .
H11A H 0.3798 -0.0531 0.2534 0.098 Uiso 1 1 calc R . .
H11B H 0.5021 -0.0026 0.3920 0.098 Uiso 1 1 calc R . .
C12 C 0.3672(5) 0.1705(5) 0.3586(4) 0.0598(12) Uani 1 1 d . . .
H12A H 0.4514 0.2487 0.4350 0.072 Uiso 1 1 calc R . .
C13 C 0.3537(7) 0.3948(6) 0.2852(5) 0.0968(17) Uani 1 1 d . . .
H13A H 0.4637 0.4669 0.3450 0.116 Uiso 1 1 calc R . .
H13B H 0.2585 0.4101 0.3162 0.116 Uiso 1 1 calc R . .
C14 C 0.3240(15) 0.4302(10) 0.1628(9) 0.195(5) Uani 1 1 d . . .
H14A H 0.4190 0.4078 0.1339 0.234 Uiso 1 1 calc R . .
H14B H 0.2162 0.3514 0.1053 0.234 Uiso 1 1 calc R . .
C15 C 0.3141(18) 0.5639(17) 0.1574(10) 0.238(6) Uani 1 1 d . . .
H15A H 0.4214 0.6435 0.2148 0.285 Uiso 1 1 calc R . .
H15B H 0.2180 0.5865 0.1849 0.285 Uiso 1 1 calc R . .
C16 C 0.2861(17) 0.5927(17) 0.0331(9) 0.269(7) Uani 1 1 d . . .
H16A H 0.2806 0.7031 0.0410 0.403 Uiso 1 1 calc R . .
H16B H 0.1780 0.5180 -0.0245 0.403 Uiso 1 1 calc R . .
H16C H 0.3822 0.5751 0.0054 0.403 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O3 C11 92.5(3) . . ?
C12 O4 C13 113.4(4) . . ?
C7 N1 C9 125.9(3) . . ?
C7 N1 C6 125.1(3) . . ?
C9 N1 C6 108.8(3) . . ?
C6 C1 C2 120.6(3) . . ?
C6 C1 C10 109.7(3) . . ?
C2 C1 C10 129.7(4) . . ?
C3 C2 C1 118.4(4) . . ?
C3 C2 H2A 120.8 . . ?
C1 C2 H2A 120.8 . . ?
C4 C3 C2 120.0(4) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C5 C4 C3 122.4(4) . . ?
C5 C4 H4A 118.8 . . ?
C3 C4 H4A 118.8 . . ?
C4 C5 C6 117.8(4) . . ?
C4 C5 H5A 121.1 . . ?
C6 C5 H5A 121.1 . . ?
C1 C6 C5 120.7(4) . . ?
C1 C6 N1 109.8(3) . . ?
C5 C6 N1 129.5(4) . . ?
O1 C7 N1 118.9(4) . . ?
O1 C7 C8 122.6(4) . . ?
N1 C7 C8 118.4(4) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 N1 126.8(4) . . ?
O2 C9 C10 125.3(4) . . ?
N1 C9 C10 107.9(3) . . ?
O3 C10 C1 118.3(3) . . ?
O3 C10 C9 113.1(3) . . ?
C1 C10 C9 103.1(3) . . ?
O3 C10 C12 89.6(3) . . ?
C1 C10 C12 118.9(3) . . ?
C9 C10 C12 114.3(3) . . ?
O3 C11 C12 91.6(3) . . ?
O3 C11 H11A 113.4 . . ?
C12 C11 H11A 113.4 . . ?
O3 C11 H11B 113.4 . . ?
C12 C11 H11B 113.4 . . ?
H11A C11 H11B 110.7 . . ?
O4 C12 C11 113.8(4) . . ?
O4 C12 C10 117.6(3) . . ?
C11 C12 C10 85.0(3) . . ?
O4 C12 H12A 112.6 . . ?
C11 C12 H12A 112.6 . . ?
C10 C12 H12A 112.6 . . ?
O4 C13 C14 105.6(5) . . ?
O4 C13 H13A 110.6 . . ?
C14 C13 H13A 110.6 . . ?
O4 C13 H13B 110.6 . . ?
C14 C13 H13B 110.6 . . ?
H13A C13 H13B 108.8 . . ?
C15 C14 C13 119.9(10) . . ?
C15 C14 H14A 107.4 . . ?
C13 C14 H14A 107.4 . . ?
C15 C14 H14B 107.4 . . ?
C13 C14 H14B 107.4 . . ?
H14A C14 H14B 106.9 . . ?
C14 C15 C16 117.6(13) . . ?
C14 C15 H15A 107.9 . . ?
C16 C15 H15A 107.9 . . ?
C14 C15 H15B 107.9 . . ?
C16 C15 H15B 107.9 . . ?
H15A C15 H15B 107.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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
O1 C7 1.225(5) . ?
O2 C9 1.207(4) . ?
O3 C10 1.439(4) . ?
O3 C11 1.448(5) . ?
O4 C12 1.389(5) . ?
O4 C13 1.424(5) . ?
N1 C7 1.409(5) . ?
N1 C9 1.413(5) . ?
N1 C6 1.431(5) . ?
C1 C6 1.388(5) . ?
C1 C2 1.392(6) . ?
C1 C10 1.486(5) . ?
C2 C3 1.382(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.382(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.365(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.391(5) . ?
C5 H5A 0.9300 . ?
C7 C8 1.485(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.525(6) . ?
C10 C12 1.571(6) . ?
C11 C12 1.514(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9800 . ?
C13 C14 1.541(10) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.206(11) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.538(12) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
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 2.4(6) . . . . ?
C10 C1 C2 C3 -178.3(4) . . . . ?
C1 C2 C3 C4 -1.7(7) . . . . ?
C2 C3 C4 C5 0.6(8) . . . . ?
C3 C4 C5 C6 -0.1(7) . . . . ?
C2 C1 C6 C5 -2.0(6) . . . . ?
C10 C1 C6 C5 178.6(3) . . . . ?
C2 C1 C6 N1 176.5(4) . . . . ?
C10 C1 C6 N1 -2.9(4) . . . . ?
C4 C5 C6 C1 0.8(6) . . . . ?
C4 C5 C6 N1 -177.3(4) . . . . ?
C7 N1 C6 C1 173.1(4) . . . . ?
C9 N1 C6 C1 -3.1(4) . . . . ?
C7 N1 C6 C5 -8.7(6) . . . . ?
C9 N1 C6 C5 175.2(4) . . . . ?
C9 N1 C7 O1 176.0(4) . . . . ?
C6 N1 C7 O1 0.4(6) . . . . ?
C9 N1 C7 C8 -3.0(6) . . . . ?
C6 N1 C7 C8 -178.5(4) . . . . ?
C7 N1 C9 O2 10.6(7) . . . . ?
C6 N1 C9 O2 -173.3(4) . . . . ?
C7 N1 C9 C10 -168.5(4) . . . . ?
C6 N1 C9 C10 7.6(4) . . . . ?
C11 O3 C10 C1 114.3(4) . . . . ?
C11 O3 C10 C9 -125.1(4) . . . . ?
C11 O3 C10 C12 -8.7(3) . . . . ?
C6 C1 C10 O3 132.8(4) . . . . ?
C2 C1 C10 O3 -46.5(6) . . . . ?
C6 C1 C10 C9 7.2(4) . . . . ?
C2 C1 C10 C9 -172.1(4) . . . . ?
C6 C1 C10 C12 -120.4(4) . . . . ?
C2 C1 C10 C12 60.3(6) . . . . ?
O2 C9 C10 O3 43.1(6) . . . . ?
N1 C9 C10 O3 -137.8(3) . . . . ?
O2 C9 C10 C1 171.9(4) . . . . ?
N1 C9 C10 C1 -9.0(4) . . . . ?
O2 C9 C10 C12 -57.6(6) . . . . ?
N1 C9 C10 C12 121.5(3) . . . . ?
C10 O3 C11 C12 9.0(3) . . . . ?
C13 O4 C12 C11 -173.6(4) . . . . ?
C13 O4 C12 C10 89.4(4) . . . . ?
O3 C11 C12 O4 -126.3(4) . . . . ?
O3 C11 C12 C10 -8.3(3) . . . . ?
O3 C10 C12 O4 122.6(4) . . . . ?
C1 C10 C12 O4 0.1(5) . . . . ?
C9 C10 C12 O4 -122.1(4) . . . . ?
O3 C10 C12 C11 8.3(3) . . . . ?
C1 C10 C12 C11 -114.2(4) . . . . ?
C9 C10 C12 C11 123.7(4) . . . . ?
C12 O4 C13 C14 -173.9(5) . . . . ?
O4 C13 C14 C15 179.9(12) . . . . ?
C13 C14 C15 C16 179.5(10) . . . . ?
loop_
_cod_changelog_entry_id
_cod_changelog_entry_author
_cod_changelog_entry_date
_cod_changelog_entry_text
1 'Vaitkus, Antanas' 2022-04-22T18:30:00+03:00
'Updated bibliographic information.'
