#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:26:14 +0100 (lun 21 de mar de 2016) $
#$Revision: 178469 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/90/4029041.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_4029041
loop_
_publ_author_name
'Lv, Jinglei'
'Zhang-Negrerie, Daisy'
'Deng, Jun'
'Du, Yunfei'
'Zhao, Kang'
_publ_section_title
;
 Metal-Free Synthesis of 2-Oxindoles via PhI(OAc)2-Mediated Oxidative C-C
 Bond Formation.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1111
_journal_paper_doi               10.1021/jo4025539
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C12 H10 N2 O'
_chemical_formula_weight         198.22
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 99.470(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8684(13)
_cell_length_b                   13.971(2)
_cell_length_c                   8.8557(16)
_cell_measurement_reflns_used    2874
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      2.6
_cell_volume                     960.2(3)
_computing_cell_refinement       Crystalclear
_computing_data_collection       Crystalclear
_computing_data_reduction        Crystalclear
_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      113(2)
_diffrn_detector_area_resol_mean 14.22
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Saturn 724 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  multilayre
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12069
_diffrn_reflns_theta_full        27.78
_diffrn_reflns_theta_max         27.78
_diffrn_reflns_theta_min         2.62
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9840
_exptl_absorpt_correction_T_min  0.9787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Crystalclear
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0563
_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 w=1/[σ²(Fo²)+(0.0576P)²+0.0569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1300
_reflns_number_gt                1854
_reflns_number_total             2270
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4025539_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4029041
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.20612(16) 0.36830(8) 0.22395(14) 0.0298(3) Uani 1 1 d .
N1 N 0.28261(17) 0.42507(9) 0.46983(15) 0.0225(3) Uani 1 1 d .
N2 N -0.0409(2) 0.60390(10) 0.06419(17) 0.0326(4) Uani 1 1 d .
C1 C 0.3788(2) 0.34145(12) 0.53921(19) 0.0262(4) Uani 1 1 d .
H1A H 0.4993 0.3441 0.5202 0.031 Uiso 1 1 calc R
H1B H 0.3254 0.2819 0.4930 0.031 Uiso 1 1 calc R
C2 C 0.3759(2) 0.34196(12) 0.71173(19) 0.0270(4) Uani 1 1 d .
H2A H 0.4533 0.2908 0.7603 0.032 Uiso 1 1 calc R
H2B H 0.2578 0.3266 0.7289 0.032 Uiso 1 1 calc R
C3 C 0.4313(2) 0.43744(12) 0.7908(2) 0.0271(4) Uani 1 1 d .
H3A H 0.4105 0.4354 0.8980 0.033 Uiso 1 1 calc R
H3B H 0.5563 0.4472 0.7925 0.033 Uiso 1 1 calc R
C4 C 0.3320(2) 0.52045(12) 0.70779(19) 0.0242(4) Uani 1 1 d .
C5 C 0.2974(2) 0.60890(13) 0.7692(2) 0.0290(4) Uani 1 1 d .
H5 H 0.3395 0.6221 0.8739 0.035 Uiso 1 1 calc R
C6 C 0.2011(2) 0.67866(13) 0.6782(2) 0.0292(4) Uani 1 1 d .
H6 H 0.1807 0.7384 0.7232 0.035 Uiso 1 1 calc R
C7 C 0.1346(2) 0.66339(12) 0.52465(19) 0.0254(4) Uani 1 1 d .
H7 H 0.0691 0.7115 0.4655 0.031 Uiso 1 1 calc R
C8 C 0.1669(2) 0.57521(11) 0.45946(19) 0.0223(4) Uani 1 1 d .
C9 C 0.2645(2) 0.50740(11) 0.55408(19) 0.0223(4) Uani 1 1 d .
C10 C 0.1257(2) 0.52995(12) 0.31024(18) 0.0228(4) Uani 1 1 d .
C11 C 0.0342(2) 0.56992(11) 0.1748(2) 0.0251(4) Uani 1 1 d .
C12 C 0.2004(2) 0.43843(12) 0.32425(19) 0.0245(4) Uani 1 1 d .
H1 H 0.143(3) 0.3811(17) 0.122(3) 0.071(8) Uiso 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0416(8) 0.0242(7) 0.0232(7) -0.0027(5) 0.0040(6) 0.0061(5)
N1 0.0253(8) 0.0205(7) 0.0215(8) 0.0017(5) 0.0032(6) 0.0025(6)
N2 0.0461(10) 0.0242(8) 0.0272(9) -0.0005(6) 0.0051(7) 0.0058(7)
C1 0.0285(9) 0.0209(8) 0.0288(10) 0.0039(7) 0.0039(7) 0.0042(7)
C2 0.0306(10) 0.0234(9) 0.0269(10) 0.0041(7) 0.0041(7) 0.0021(7)
C3 0.0272(9) 0.0272(9) 0.0257(9) 0.0030(7) 0.0009(7) -0.0016(7)
C4 0.0240(9) 0.0236(9) 0.0246(9) 0.0005(7) 0.0032(7) -0.0030(7)
C5 0.0347(10) 0.0267(9) 0.0247(10) -0.0031(7) 0.0023(8) -0.0030(8)
C6 0.0357(10) 0.0234(9) 0.0286(10) -0.0039(7) 0.0058(8) 0.0006(7)
C7 0.0295(9) 0.0213(8) 0.0262(9) 0.0029(7) 0.0064(7) 0.0016(7)
C8 0.0223(9) 0.0224(9) 0.0227(9) 0.0015(7) 0.0055(7) -0.0016(6)
C9 0.0227(9) 0.0196(8) 0.0251(9) 0.0002(7) 0.0048(7) -0.0021(6)
C10 0.0239(9) 0.0216(8) 0.0234(9) 0.0022(7) 0.0053(7) 0.0004(7)
C11 0.0327(10) 0.0180(8) 0.0253(10) -0.0029(7) 0.0068(7) 0.0005(7)
C12 0.0263(9) 0.0241(9) 0.0237(9) -0.0005(7) 0.0057(7) -0.0006(7)
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
C12 O1 H1 114.6(14)
C12 N1 C9 108.72(13)
C12 N1 C1 129.67(14)
C9 N1 C1 121.60(13)
N1 C1 C2 108.78(13)
N1 C1 H1A 109.9
C2 C1 H1A 109.9
N1 C1 H1B 109.9
C2 C1 H1B 109.9
H1A C1 H1B 108.3
C1 C2 C3 114.15(14)
C1 C2 H2A 108.7
C3 C2 H2A 108.7
C1 C2 H2B 108.7
C3 C2 H2B 108.7
H2A C2 H2B 107.6
C4 C3 C2 110.96(14)
C4 C3 H3A 109.4
C2 C3 H3A 109.4
C4 C3 H3B 109.4
C2 C3 H3B 109.4
H3A C3 H3B 108.0
C9 C4 C5 115.49(15)
C9 C4 C3 117.21(15)
C5 C4 C3 127.29(15)
C4 C5 C6 120.86(16)
C4 C5 H5 119.6
C6 C5 H5 119.6
C7 C6 C5 122.35(16)
C7 C6 H6 118.8
C5 C6 H6 118.8
C6 C7 C8 118.24(16)
C6 C7 H7 120.9
C8 C7 H7 120.9
C7 C8 C9 117.71(15)
C7 C8 C10 136.80(16)
C9 C8 C10 105.49(14)
C4 C9 N1 125.28(15)
C4 C9 C8 125.36(15)
N1 C9 C8 109.37(14)
C12 C10 C11 125.73(15)
C12 C10 C8 106.76(14)
C11 C10 C8 127.47(15)
N2 C11 C10 179.16(18)
O1 C12 N1 118.08(15)
O1 C12 C10 132.24(16)
N1 C12 C10 109.66(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C12 1.3281(19)
O1 H1 0.97(3)
N1 C12 1.357(2)
N1 C9 1.391(2)
N1 C1 1.471(2)
N2 C11 1.159(2)
C1 C2 1.532(2)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.536(2)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.519(2)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C9 1.390(2)
C4 C5 1.395(2)
C5 C6 1.404(2)
C5 H5 0.9500
C6 C7 1.391(2)
C6 H6 0.9500
C7 C8 1.401(2)
C7 H7 0.9500
C8 C9 1.406(2)
C8 C10 1.453(2)
C10 C12 1.404(2)
C10 C11 1.409(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N2 0.97(3) 1.73(3) 2.694(2) 175(2) 3_565
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 N1 C1 C2 -154.67(16)
C9 N1 C1 C2 25.6(2)
N1 C1 C2 C3 -51.04(19)
C1 C2 C3 C4 51.1(2)
C2 C3 C4 C9 -24.0(2)
C2 C3 C4 C5 154.63(16)
C9 C4 C5 C6 -0.4(2)
C3 C4 C5 C6 -179.06(16)
C4 C5 C6 C7 0.6(3)
C5 C6 C7 C8 -0.5(3)
C6 C7 C8 C9 0.2(2)
C6 C7 C8 C10 -179.63(18)
C5 C4 C9 N1 -179.82(15)
C3 C4 C9 N1 -1.0(2)
C5 C4 C9 C8 0.0(2)
C3 C4 C9 C8 178.88(15)
C12 N1 C9 C4 -179.79(16)
C1 N1 C9 C4 0.0(2)
C12 N1 C9 C8 0.33(18)
C1 N1 C9 C8 -179.89(14)
C7 C8 C9 C4 0.1(2)
C10 C8 C9 C4 179.91(15)
C7 C8 C9 N1 179.94(14)
C10 C8 C9 N1 -0.21(18)
C7 C8 C10 C12 179.83(18)
C9 C8 C10 C12 0.02(18)
C7 C8 C10 C11 2.0(3)
C9 C8 C10 C11 -177.84(16)
C12 C10 C11 N2 -167(13)
C8 C10 C11 N2 10(13)
C9 N1 C12 O1 178.47(14)
C1 N1 C12 O1 -1.3(3)
C9 N1 C12 C10 -0.31(18)
C1 N1 C12 C10 179.93(15)
C11 C10 C12 O1 -0.5(3)
C8 C10 C12 O1 -178.37(17)
C11 C10 C12 N1 178.09(16)
C8 C10 C12 N1 0.18(18)
