#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/50/4025069.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_4025069
loop_
_publ_author_name
'Tao-Shan Jiang'
'Ri-Yuan Tang'
'Xing-Guo Zhang'
'Xin-Hua Li'
'Jin-Heng Li'
_publ_section_title
;
Palladium-Catalyzed Intramolecular 5-exo-dig Hydroarylations
of N-Arylpropiolamides: Thermodynamics-Controlled Stereoselective Synthesis
of 3-Methyleneoxindoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8834
_journal_page_last               8837
_journal_paper_doi               10.1021/jo901963g
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C16 H13 N O'
_chemical_formula_sum            'C16 H13 N O'
_chemical_formula_weight         235.27
_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                 109.502(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.549(10)
_cell_length_b                   5.6866(18)
_cell_length_c                   15.507(5)
_cell_measurement_reflns_used    688
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.044
_cell_measurement_theta_min      2.945
_cell_volume                     2456.2(14)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL(Bruker, 2002)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scan'
_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  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0542
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6125
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.68
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9866
_exptl_absorpt_correction_T_min  0.9773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.256
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2164
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.256
_refine_ls_R_factor_all          0.1304
_refine_ls_R_factor_gt           0.1013
_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)+(0.0662P)²+2.7582P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1966
_refine_ls_wR_factor_ref         0.2101
_reflns_number_gt                1673
_reflns_number_total             2164
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo901963g_si_003.cif
_cod_data_source_block           2241m
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4025069
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.20611(9) 0.5906(5) 0.10272(19) 0.0522(8) Uani 1 1 d . . .
N1 N 0.16252(10) 0.3453(5) 0.1606(2) 0.0393(8) Uani 1 1 d . . .
C1 C 0.17318(14) 0.9796(7) -0.0332(3) 0.0502(11) Uani 1 1 d . . .
H1 H 0.1929 0.8573 -0.0025 0.060 Uiso 1 1 calc R . .
C2 C 0.19039(15) 1.1409(8) -0.0806(3) 0.0593(12) Uani 1 1 d . . .
H2 H 0.2216 1.1271 -0.0815 0.071 Uiso 1 1 calc R . .
C3 C 0.16189(17) 1.3220(8) -0.1266(3) 0.0590(12) Uani 1 1 d . . .
H3 H 0.1741 1.4319 -0.1574 0.071 Uiso 1 1 calc R . .
C4 C 0.11539(17) 1.3421(7) -0.1274(3) 0.0610(12) Uani 1 1 d . . .
H4 H 0.0958 1.4629 -0.1597 0.073 Uiso 1 1 calc R . .
C5 C 0.09823(15) 1.1814(7) -0.0796(3) 0.0501(11) Uani 1 1 d . . .
H5 H 0.0668 1.1960 -0.0800 0.060 Uiso 1 1 calc R . .
C6 C 0.12655(13) 0.9965(6) -0.0304(2) 0.0406(9) Uani 1 1 d . . .
C7 C 0.10507(12) 0.8384(6) 0.0191(2) 0.0413(10) Uani 1 1 d . . .
H7 H 0.0731 0.8755 0.0096 0.050 Uiso 1 1 calc R . .
C8 C 0.11991(12) 0.6525(6) 0.0750(2) 0.0365(9) Uani 1 1 d . . .
C9 C 0.08878(12) 0.5158(6) 0.1128(2) 0.0373(9) Uani 1 1 d . . .
C10 C 0.04133(13) 0.5365(7) 0.1059(3) 0.0489(11) Uani 1 1 d . . .
H10 H 0.0230 0.6612 0.0737 0.059 Uiso 1 1 calc R . .
C11 C 0.02108(15) 0.3707(8) 0.1471(3) 0.0585(12) Uani 1 1 d . . .
H11 H -0.0109 0.3848 0.1430 0.070 Uiso 1 1 calc R . .
C12 C 0.04809(15) 0.1845(8) 0.1942(3) 0.0581(12) Uani 1 1 d . . .
H12 H 0.0337 0.0730 0.2206 0.070 Uiso 1 1 calc R . .
C13 C 0.09605(14) 0.1597(7) 0.2032(3) 0.0483(10) Uani 1 1 d . . .
H13 H 0.1144 0.0355 0.2358 0.058 Uiso 1 1 calc R . .
C14 C 0.11535(12) 0.3270(6) 0.1616(2) 0.0379(9) Uani 1 1 d . . .
C15 C 0.16781(13) 0.5368(6) 0.1107(2) 0.0371(9) Uani 1 1 d . . .
C16 C 0.20134(14) 0.1849(7) 0.2064(3) 0.0548(11) Uani 1 1 d . . .
H16A H 0.2266 0.2165 0.1786 0.066 Uiso 1 1 d R . .
H16B H 0.2141 0.2299 0.2691 0.066 Uiso 1 1 d R . .
H16C H 0.1919 0.0307 0.1977 0.066 Uiso 1 1 d 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
C15 N1 C14 111.4(3) . . ?
C15 N1 C16 123.6(3) . . ?
C14 N1 C16 125.0(3) . . ?
C2 C1 C6 121.0(4) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.4(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.1(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 122.1(4) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C5 116.8(4) . . ?
C1 C6 C7 125.6(3) . . ?
C5 C6 C7 117.6(3) . . ?
C8 C7 C6 135.9(3) . . ?
C8 C7 H7 112.0 . . ?
C6 C7 H7 112.0 . . ?
C7 C8 C9 124.1(3) . . ?
C7 C8 C15 130.7(3) . . ?
C9 C8 C15 105.2(3) . . ?
C10 C9 C14 118.9(3) . . ?
C10 C9 C8 133.0(3) . . ?
C14 C9 C8 108.1(3) . . ?
C9 C10 C11 119.5(4) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 120.3(4) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 121.5(4) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 117.0(4) . . ?
C14 C13 H13 121.5 . . ?
C12 C13 H13 121.5 . . ?
C13 C14 C9 122.7(3) . . ?
C13 C14 N1 128.7(3) . . ?
C9 C14 N1 108.6(3) . . ?
O1 C15 N1 122.7(3) . . ?
O1 C15 C8 130.6(3) . . ?
N1 C15 C8 106.7(3) . . ?
N1 C16 H16A 104.9 . . ?
N1 C16 H16B 108.1 . . ?
H16A C16 H16B 107.2 . . ?
N1 C16 H16C 112.1 . . ?
H16A C16 H16C 110.1 . . ?
H16B C16 H16C 113.9 . . ?
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 C15 1.218(4) . ?
N1 C15 1.375(4) . ?
N1 C14 1.403(4) . ?
N1 C16 1.452(4) . ?
C1 C2 1.375(5) . ?
C1 C6 1.396(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.370(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.458(5) . ?
C7 C8 1.345(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.468(5) . ?
C8 C15 1.490(5) . ?
C9 C10 1.375(5) . ?
C9 C14 1.394(5) . ?
C10 C11 1.382(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(5) . ?
C13 H13 0.9300 . ?
C16 H16A 0.9945 . ?
C16 H16B 0.9530 . ?
C16 H16C 0.9170 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4557672
