#------------------------------------------------------------------------------
#$Date: 2019-11-28 18:44:59 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244327 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/87/7238746.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_7238746
loop_
_publ_author_name
'Moran, Wesley J.'
'MacRory, Kerry L.'
'Rodríguez, Arantxa'
_publ_section_title
;
 Oxidative rearrangement of indoles to oxindoles
;
_journal_issue                   24
_journal_name_full               'RSC Advances'
_journal_page_first              8962
_journal_paper_doi               10.1039/c2ra21800c
_journal_volume                  2
_journal_year                    2012
_chemical_formula_sum            'C17 H19 N O5'
_chemical_formula_weight         317.34
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 111.05(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.215(13)
_cell_length_b                   7.397(7)
_cell_length_c                   16.759(15)
_cell_measurement_temperature    296(2)
_cell_volume                     1645(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14451
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9632
_exptl_absorpt_correction_T_min  0.9543
_exptl_absorpt_process_details   multiscan
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.008(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0619P)²+0.3216P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1363
_reflns_number_gt                2573
_reflns_number_total             3761
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ra21800c.txt
_cod_data_source_block           mo_wesley_unknown1_0m
_cod_database_code               7238746
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C8 C 0.39608(12) 0.2847(2) 0.31725(11) 0.0439(4) Uani 1 1 d .
C1 C 0.44059(12) 0.2397(2) 0.45951(10) 0.0411(4) Uani 1 1 d .
C7 C 0.50869(11) 0.3112(2) 0.35737(10) 0.0392(4) Uani 1 1 d .
C6 C 0.53167(11) 0.2826(2) 0.44853(10) 0.0384(4) Uani 1 1 d .
C5 C 0.61820(12) 0.2887(2) 0.51951(10) 0.0466(4) Uani 1 1 d .
H5 H 0.6796 0.3160 0.5143 0.056 Uiso 1 1 calc R
C2 C 0.43486(14) 0.2059(3) 0.53820(11) 0.0540(5) Uani 1 1 d .
H2 H 0.3738 0.1782 0.5440 0.065 Uiso 1 1 calc R
C3 C 0.52274(15) 0.2145(3) 0.60804(12) 0.0586(5) Uani 1 1 d .
H3 H 0.5212 0.1935 0.6623 0.070 Uiso 1 1 calc R
C4 C 0.61322(14) 0.2536(3) 0.59909(11) 0.0545(5) Uani 1 1 d .
H4 H 0.6719 0.2565 0.6473 0.065 Uiso 1 1 calc R
C10 C 0.67256(13) 0.3724(3) 0.33550(12) 0.0517(4) Uani 1 1 d .
C9 C 0.56200(12) 0.3488(2) 0.30659(10) 0.0432(4) Uani 1 1 d .
C11 C 0.51146(13) 0.3804(3) 0.21223(11) 0.0496(4) Uani 1 1 d .
C12 C 0.25757(12) 0.1904(3) 0.36656(12) 0.0533(5) Uani 1 1 d .
H12A H 0.2568 0.0958 0.4064 0.064 Uiso 1 1 calc R
H12B H 0.2263 0.1427 0.3091 0.064 Uiso 1 1 calc R
C13 C 0.19650(15) 0.3485(3) 0.37766(18) 0.0820(7) Uani 1 1 d .
H13A H 0.2261 0.3945 0.4349 0.123 Uiso 1 1 calc R
H13B H 0.1287 0.3099 0.3675 0.123 Uiso 1 1 calc R
H13C H 0.1959 0.4419 0.3377 0.123 Uiso 1 1 calc R
N1 N 0.36207(9) 0.23840(19) 0.38070(9) 0.0451(3) Uani 1 1 d .
O1 O 0.34564(9) 0.2992(2) 0.24221(8) 0.0615(4) Uani 1 1 d .
O3 O 0.70339(9) 0.36872(18) 0.26960(8) 0.0589(4) Uani 1 1 d .
O2 O 0.72790(11) 0.3936(3) 0.40654(9) 0.1004(7) Uani 1 1 d .
O4 O 0.49211(11) 0.5300(2) 0.18256(9) 0.0710(4) Uani 1 1 d .
O5 O 0.49908(10) 0.22654(18) 0.16822(8) 0.0586(4) Uani 1 1 d .
C16 C 0.4532(2) 0.2419(4) 0.07604(13) 0.0824(7) Uani 1 1 d .
H16A H 0.4090 0.3463 0.0615 0.099 Uiso 1 1 calc R
H16B H 0.4128 0.1353 0.0532 0.099 Uiso 1 1 calc R
C14 C 0.80981(15) 0.3873(3) 0.28616(15) 0.0752(6) Uani 1 1 d .
H14A H 0.8466 0.2884 0.3218 0.090 Uiso 1 1 calc R
H14B H 0.8346 0.4999 0.3160 0.090 Uiso 1 1 calc R
C15 C 0.82527(19) 0.3856(4) 0.20301(17) 0.0883(8) Uani 1 1 d .
H15A H 0.8037 0.2714 0.1752 0.133 Uiso 1 1 calc R
H15B H 0.8954 0.4032 0.2128 0.133 Uiso 1 1 calc R
H15C H 0.7866 0.4810 0.1673 0.133 Uiso 1 1 calc R
C17 C 0.5316(2) 0.2610(4) 0.03672(16) 0.1049(10) Uani 1 1 d .
H17A H 0.5706 0.3680 0.0584 0.157 Uiso 1 1 calc R
H17B H 0.4995 0.2700 -0.0243 0.157 Uiso 1 1 calc R
H17C H 0.5750 0.1572 0.0507 0.157 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
O1 C8 N1 126.25(16)
O1 C8 C7 126.15(15)
N1 C8 C7 107.59(14)
C2 C1 N1 127.37(16)
C2 C1 C6 122.77(15)
N1 C1 C6 109.86(15)
C9 C7 C6 136.20(15)
C9 C7 C8 119.29(15)
C6 C7 C8 104.50(13)
C5 C6 C1 118.33(16)
C5 C6 C7 134.26(15)
C1 C6 C7 107.41(14)
C6 C5 C4 119.29(17)
C3 C2 C1 117.43(18)
C2 C3 C4 121.07(18)
C3 C4 C5 121.10(17)
O2 C10 O3 122.93(17)
O2 C10 C9 126.29(16)
O3 C10 C9 110.77(16)
C7 C9 C10 125.88(16)
C7 C9 C11 121.93(16)
C10 C9 C11 112.13(14)
O4 C11 O5 126.25(18)
O4 C11 C9 121.97(17)
O5 C11 C9 111.61(16)
N1 C12 C13 112.85(16)
C8 N1 C1 110.57(15)
C8 N1 C12 124.07(15)
C1 N1 C12 125.34(15)
C10 O3 C14 118.35(16)
C11 O5 C16 116.25(17)
O5 C16 C17 110.9(2)
O3 C14 C15 108.45(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C8 O1 1.208(2)
C8 N1 1.361(2)
C8 C7 1.510(2)
C1 C2 1.373(3)
C1 N1 1.390(2)
C1 C6 1.408(2)
C7 C9 1.356(2)
C7 C6 1.458(3)
C6 C5 1.371(2)
C5 C4 1.385(3)
C2 C3 1.372(3)
C3 C4 1.378(3)
C10 O2 1.178(2)
C10 O3 1.327(2)
C10 C9 1.479(3)
C9 C11 1.502(3)
C11 O4 1.204(2)
C11 O5 1.333(2)
C12 N1 1.461(2)
C12 C13 1.507(3)
O3 C14 1.443(3)
O5 C16 1.449(3)
C16 C17 1.490(4)
C14 C15 1.487(3)
