#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/70/1507029.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_1507029
loop_
_publ_author_name
'Teichert, Antje'
'Jantos, Katja'
'Harms, Klaus'
'Studer, Armido'
_publ_section_title
;
 One-pot homolytic aromatic substitutions/HWE olefinations under microwave
 conditions for the formation of a small oxindole library.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              3477
_journal_page_last               3480
_journal_paper_doi               10.1021/ol048759t
_journal_volume                  6
_journal_year                    2004
_chemical_formula_moiety         'C16 H12 N2 O3'
_chemical_formula_sum            'C16 H12 N2 O3'
_chemical_formula_weight         280.28
_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_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.095(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5880(8)
_cell_length_b                   21.2436(17)
_cell_length_c                   7.9723(9)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1284.2(2)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.894
_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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9594
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.22
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.0376
_exptl_absorpt_correction_T_min  0.9342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;

 ?

;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.020(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   1.041
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2563
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0342
_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)+(0.0486P)²+0.1715P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0908
_reflns_number_gt                2049
_reflns_number_total             2563
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol048759tsi20040630_105158.cif
_cod_data_source_block           teich02
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1507029
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
C1 C 0.24874(17) 0.30110(6) 0.93692(18) 0.0370(3) Uani 1 1 d
C3 C 0.40681(16) 0.21345(6) 0.99060(17) 0.0335(3) Uani 1 1 d
C4 C 0.4555(2) 0.15144(7) 1.0014(2) 0.0419(3) Uani 1 1 d
C5 C 0.6158(2) 0.13865(7) 1.0718(2) 0.0460(4) Uani 1 1 d
C6 C 0.72059(19) 0.18658(7) 1.1315(2) 0.0419(3) Uani 1 1 d
C7 C 0.66977(18) 0.24897(7) 1.11980(18) 0.0378(3) Uani 1 1 d
C8 C 0.51226(16) 0.26332(6) 1.04497(17) 0.0328(3) Uani 1 1 d
C9 C 0.41812(16) 0.32170(6) 1.01196(17) 0.0349(3) Uani 1 1 d
C10 C 0.44584(18) 0.38321(7) 1.03832(19) 0.0387(3) Uani 1 1 d
C11 C 0.59933(16) 0.41574(6) 1.10025(18) 0.0357(3) Uani 1 1 d
C12 C 0.58666(18) 0.46979(7) 1.2040(2) 0.0411(3) Uani 1 1 d
C13 C 0.72830(18) 0.50129(7) 1.2664(2) 0.0405(3) Uani 1 1 d
C14 C 0.88375(16) 0.47876(6) 1.22114(17) 0.0361(3) Uani 1 1 d
C15 C 0.90121(17) 0.42741(6) 1.11239(19) 0.0381(3) Uani 1 1 d
C16 C 0.75830(18) 0.39621(6) 1.05160(19) 0.0378(3) Uani 1 1 d
C17 C 0.1080(2) 0.19855(9) 0.8748(3) 0.0491(4) Uani 1 1 d
N2 N 0.25167(13) 0.23707(5) 0.92655(15) 0.0365(3) Uani 1 1 d
N14 N 1.03480(15) 0.51069(6) 1.29108(16) 0.0429(3) Uani 1 1 d
O1 O 0.12936(13) 0.33451(5) 0.89360(15) 0.0508(3) Uani 1 1 d
O2 O 1.01831(14) 0.55878(5) 1.37801(16) 0.0538(3) Uani 1 1 d
O3 O 1.17166(13) 0.48721(6) 1.26152(17) 0.0623(4) Uani 1 1 d
H4 H 0.384(2) 0.1200(9) 0.959(2) 0.057(5) Uiso 1 1 d
H5 H 0.652(2) 0.0948(8) 1.081(2) 0.051(4) Uiso 1 1 d
H6 H 0.831(2) 0.1770(7) 1.188(2) 0.048(4) Uiso 1 1 d
H7 H 0.741(2) 0.2825(7) 1.162(2) 0.041(4) Uiso 1 1 d
H10 H 0.351(2) 0.4103(7) 1.011(2) 0.046(4) Uiso 1 1 d
H12 H 0.475(2) 0.4853(8) 1.233(2) 0.050(4) Uiso 1 1 d
H13 H 0.722(2) 0.5371(8) 1.338(2) 0.049(4) Uiso 1 1 d
H15 H 1.012(2) 0.4139(8) 1.080(2) 0.053(5) Uiso 1 1 d
H16 H 0.7697(19) 0.3603(7) 0.9720(19) 0.041(4) Uiso 1 1 d
H17A H 0.020(3) 0.2266(10) 0.849(3) 0.080(7) Uiso 1 1 d
H17B H 0.081(3) 0.1704(10) 0.971(3) 0.074(6) Uiso 1 1 d
H17C H 0.131(3) 0.1720(11) 0.772(3) 0.087(7) 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
O1 C1 N2 126.20(12)
O1 C1 C9 125.92(13)
N2 C1 C9 107.88(11)
N2 C3 C4 127.25(13)
N2 C3 C8 108.46(11)
C4 C3 C8 124.29(13)
C5 C4 C3 117.20(14)
C5 C4 H4 121.2(11)
C3 C4 H4 121.5(11)
C4 C5 C6 119.96(14)
C4 C5 H5 118.2(10)
C6 C5 H5 121.8(10)
C5 C6 C7 122.23(14)
C5 C6 H6 119.5(10)
C7 C6 H6 118.2(10)
C8 C7 C6 119.09(14)
C8 C7 H7 118.1(9)
C6 C7 H7 122.8(9)
C7 C8 C3 117.16(12)
C7 C8 C9 134.02(13)
C3 C8 C9 108.76(11)
C10 C9 C8 137.09(12)
C10 C9 C1 119.09(12)
C8 C9 C1 103.75(11)
C9 C10 C11 130.43(13)
C9 C10 H10 116.6(10)
C11 C10 H10 113.0(10)
C16 C11 C12 119.83(12)
C16 C11 C10 118.67(13)
C12 C11 C10 121.42(12)
C13 C12 C11 123.16(13)
C13 C12 H12 116.4(10)
C11 C12 H12 120.4(10)
C14 C13 C12 115.06(14)
C14 C13 H13 120.8(10)
C12 C13 H13 124.1(10)
C13 C14 C15 123.38(13)
C13 C14 N14 115.41(13)
C15 C14 N14 121.22(12)
C16 C15 C14 120.83(13)
C16 C15 H15 117.9(11)
C14 C15 H15 121.2(11)
C11 C16 C15 117.59(14)
C11 C16 H16 121.2(9)
C15 C16 H16 121.2(9)
N2 C17 H17A 103.7(14)
N2 C17 H17B 107.4(12)
H17A C17 H17B 113.1(18)
N2 C17 H17C 113.9(13)
H17A C17 H17C 109.2(19)
H17B C17 H17C 109.6(17)
C3 N2 C1 111.14(11)
C3 N2 C17 122.93(13)
C1 N2 C17 125.57(12)
O3 N14 O2 124.35(13)
O3 N14 C14 114.82(13)
O2 N14 C14 120.82(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.1920(16)
C1 N2 1.3630(17)
C1 C9 1.4646(18)
C3 N2 1.3617(17)
C3 C4 1.3701(19)
C3 C8 1.3875(19)
C4 C5 1.348(2)
C4 H4 0.917(19)
C5 C6 1.367(2)
C5 H5 0.974(17)
C6 C7 1.383(2)
C6 H6 0.957(17)
C7 C8 1.3510(19)
C7 H7 0.950(16)
C8 C9 1.4504(18)
C9 C10 1.3389(19)
C10 C11 1.4268(18)
C10 H10 0.939(17)
C11 C16 1.3460(18)
C11 C12 1.420(2)
C12 C13 1.346(2)
C12 H12 0.946(17)
C13 C14 1.3347(19)
C13 H13 0.955(17)
C14 C15 1.403(2)
C14 N14 1.4275(17)
C15 C16 1.3460(19)
C15 H15 0.932(18)
C16 H16 0.997(16)
C17 N2 1.4128(18)
C17 H17A 0.91(2)
C17 H17B 1.00(2)
C17 H17C 1.02(2)
N14 O3 1.1836(16)
N14 O2 1.2433(17)
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
N2 C3 C4 C5 -179.21(14)
C8 C3 C4 C5 1.0(2)
C3 C4 C5 C6 1.2(2)
C4 C5 C6 C7 -1.3(2)
C5 C6 C7 C8 -0.8(2)
C6 C7 C8 C3 2.8(2)
C6 C7 C8 C9 179.60(14)
N2 C3 C8 C7 177.13(12)
C4 C3 C8 C7 -3.0(2)
N2 C3 C8 C9 -0.42(15)
C4 C3 C8 C9 179.44(13)
C7 C8 C9 C10 0.8(3)
C3 C8 C9 C10 177.81(17)
C7 C8 C9 C1 -175.99(15)
C3 C8 C9 C1 0.97(14)
O1 C1 C9 C10 0.9(2)
N2 C1 C9 C10 -178.72(13)
O1 C1 C9 C8 178.43(14)
N2 C1 C9 C8 -1.19(15)
C8 C9 C10 C11 7.2(3)
C1 C9 C10 C11 -176.33(15)
C9 C10 C11 C16 38.9(2)
C9 C10 C11 C12 -144.49(16)
C16 C11 C12 C13 -4.2(2)
C10 C11 C12 C13 179.21(15)
C11 C12 C13 C14 1.2(2)
C12 C13 C14 C15 2.0(2)
C12 C13 C14 N14 -178.10(13)
C13 C14 C15 C16 -2.4(2)
N14 C14 C15 C16 177.68(13)
C12 C11 C16 C15 3.7(2)
C10 C11 C16 C15 -179.65(13)
C14 C15 C16 C11 -0.6(2)
C4 C3 N2 C1 179.77(14)
C8 C3 N2 C1 -0.38(15)
C4 C3 N2 C17 6.3(2)
C8 C3 N2 C17 -173.80(14)
O1 C1 N2 C3 -178.61(14)
C9 C1 N2 C3 1.01(15)
O1 C1 N2 C17 -5.4(2)
C9 C1 N2 C17 174.22(14)
C13 C14 N14 O3 174.01(14)
C15 C14 N14 O3 -6.1(2)
C13 C14 N14 O2 -4.9(2)
C15 C14 N14 O2 175.01(13)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 1838249 ChemSpider
