#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/87/1508762.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_1508762
loop_
_publ_author_name
'Ghosh, Santanu'
'De, Subhadip'
'Kakde, Badrinath N.'
'Bhunia, Subhajit'
'Adhikary, Amit'
'Bisai, Alakesh'
_publ_section_title
;
 Intramolecular Dehydrogenative Coupling of sp(2) C-H and sp(3) C-H Bonds:
 An Expeditious Route to 2-Oxindoles.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5864
_journal_page_last               5867
_journal_paper_doi               10.1021/ol302767w
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C24 H24 N2 O6'
_chemical_formula_sum            'C24 H24 N2 O6'
_chemical_formula_weight         436.45
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 94.938(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2477(9)
_cell_length_b                   15.824(2)
_cell_length_c                   16.2391(17)
_cell_measurement_temperature    296(2)
_cell_volume                     2111.5(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_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  0.0722
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16893
_diffrn_reflns_theta_full        29.78
_diffrn_reflns_theta_max         29.78
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   'Empirical''Bruker SADABS V2.10'
_exptl_absorpt_process_details   'Bruker SADABS V2.10'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0525
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1933
_refine_ls_wR_factor_ref         0.2203
_reflns_number_gt                2415
_reflns_number_total             2935
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302767w_si_002.cif
_cod_data_source_block           Alakesh
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C24 H24 N2 O6 '
_cod_database_code               1508762
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'
'-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
O1 O 0.67184(12) 0.15965(6) 0.19167(7) 0.0339(3) Uani 1 1 d .
O2 O 0.90735(13) 0.22161(5) 0.16594(7) 0.0336(3) Uani 1 1 d .
O3 O 0.81609(13) 0.12392(6) 0.37801(6) 0.0338(3) Uani 1 1 d .
C7 C 0.6665(3) -0.03805(11) 0.38459(11) 0.0429(4) Uani 1 1 d .
C10 C 0.85251(15) 0.00836(7) 0.19169(8) 0.0229(3) Uani 1 1 d .
C11 C 0.90539(14) 0.08762(6) 0.24037(8) 0.0213(3) Uani 1 1 d .
C9 C 0.57710(19) 0.22121(8) 0.14083(10) 0.0371(4) Uani 1 1 d .
H3A H 0.6298 0.2760 0.1462 0.045 Uiso 1 1 calc R
H3B H 0.4697 0.2264 0.1603 0.045 Uiso 1 1 calc R
C8 C 0.83377(15) 0.16579(7) 0.19491(8) 0.0241(3) Uani 1 1 d .
C12 C 0.81979(14) 0.07489(7) 0.32092(8) 0.0243(3) Uani 1 1 d .
N6 N 0.74966(14) -0.00339(6) 0.31746(7) 0.0264(3) Uani 1 1 d .
C1 C 0.73404(17) -0.14638(8) 0.13564(10) 0.0326(4) Uani 1 1 d .
H1 H 0.6968 -0.1989 0.1165 0.039 Uiso 1 1 calc R
C2 C 0.70767(16) -0.12166(7) 0.21525(9) 0.0299(3) Uani 1 1 d .
H2 H 0.6526 -0.1564 0.2496 0.036 Uiso 1 1 calc R
C3 C 0.76640(15) -0.04318(7) 0.24187(8) 0.0242(3) Uani 1 1 d .
C4 C 0.87458(16) -0.01601(7) 0.11216(8) 0.0270(3) Uani 1 1 d .
H4 H 0.9285 0.0191 0.0776 0.032 Uiso 1 1 calc R
C5 C 0.81461(18) -0.09454(8) 0.08399(9) 0.0319(4) Uani 1 1 d .
H5 H 0.8290 -0.1119 0.0304 0.038 Uiso 1 1 calc R
C6 C 0.5612(2) 0.19556(12) 0.05240(12) 0.0510(5) Uani 1 1 d .
H6A H 0.6674 0.1910 0.0328 0.077 Uiso 1 1 calc R
H6B H 0.4989 0.2372 0.0204 0.077 Uiso 1 1 calc R
H6C H 0.5071 0.1419 0.0469 0.077 Uiso 1 1 calc R
H12 H 0.687(3) -0.0100(15) 0.4322(18) 0.077(8) Uiso 1 1 d .
H10 H 0.669(3) -0.0921(15) 0.3837(17) 0.075(8) Uiso 1 1 d .
H11 H 0.544(4) -0.0272(19) 0.374(2) 0.105(10) Uiso 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_3
C8 O1 C9 117.30(10) .
N6 C7 H12 113.2(17) .
N6 C7 H10 110.5(19) .
H12 C7 H10 120(2) .
N6 C7 H11 109.1(19) .
H12 C7 H11 101(2) .
H10 C7 H11 101(2) .
C4 C10 C3 120.10(11) .
C4 C10 C11 131.46(11) .
C3 C10 C11 108.43(11) .
C10 C11 C8 109.43(10) .
C10 C11 C12 101.50(9) .
C8 C11 C12 109.04(9) .
C10 C11 C11 109.83(8) 2_755
C8 C11 C11 115.64(8) 2_755
C12 C11 C11 110.46(12) 2_755
O1 C9 C6 111.25(12) .
O1 C9 H3A 109.4 .
C6 C9 H3A 109.4 .
O1 C9 H3B 109.4 .
C6 C9 H3B 109.4 .
H3A C9 H3B 108.0 .
O2 C8 O1 125.46(11) .
O2 C8 C11 126.89(11) .
O1 C8 C11 107.64(9) .
O3 C12 N6 125.01(12) .
O3 C12 C11 127.24(11) .
N6 C12 C11 107.74(10) .
C12 N6 C3 111.79(10) .
C12 N6 C7 122.68(12) .
C3 N6 C7 125.52(11) .
C5 C1 C2 121.36(12) .
C5 C1 H1 119.3 .
C2 C1 H1 119.3 .
C1 C2 C3 117.67(12) .
C1 C2 H2 121.2 .
C3 C2 H2 121.2 .
C2 C3 C10 121.62(12) .
C2 C3 N6 128.21(12) .
C10 C3 N6 110.16(10) .
C10 C4 C5 118.97(12) .
C10 C4 H4 120.5 .
C5 C4 H4 120.5 .
C1 C5 C4 120.20(13) .
C1 C5 H5 119.9 .
C4 C5 H5 119.9 .
C9 C6 H6A 109.5 .
C9 C6 H6B 109.5 .
H6A C6 H6B 109.5 .
C9 C6 H6C 109.5 .
H6A C6 H6C 109.5 .
H6B C6 H6C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C8 1.3356(15) .
O1 C9 1.4594(15) .
O2 C8 1.1912(15) .
O3 C12 1.2113(16) .
C7 N6 1.4451(19) .
C7 H12 0.90(3) .
C7 H10 0.86(2) .
C7 H11 1.02(3) .
C10 C4 1.3748(18) .
C10 C3 1.3905(17) .
C10 C11 1.5261(15) .
C11 C8 1.5325(15) .
C11 C12 1.5522(18) .
C11 C11 1.565(2) 2_755
C9 C6 1.487(2) .
C9 H3A 0.9700 .
C9 H3B 0.9700 .
C12 N6 1.3662(15) .
N6 C3 1.3971(17) .
C1 C5 1.383(2) .
C1 C2 1.386(2) .
C1 H1 0.9300 .
C2 C3 1.3883(16) .
C2 H2 0.9300 .
C4 C5 1.3997(16) .
C4 H4 0.9300 .
C5 H5 0.9300 .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
