#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/45/4024517.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_4024517
loop_
_publ_author_name
'Peng Peng'
'Bo-Xiao Tang'
'Shao-Feng Pi'
'Yun Liang'
'Jin-Heng Li'
_publ_section_title
;
Synthesis of (E)-3-(Isobenzofuran-3(1H)-ylidene)indolin-2-ones by the
Palladium-Catalyzed Intramolecular C-H Functionalization Process
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3569
_journal_page_last               3572
_journal_paper_doi               10.1021/jo900437p
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C18 H15 N O2'
_chemical_formula_sum            'C18 H15 N O2'
_chemical_formula_weight         277.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   '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                 105.711(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5969(17)
_cell_length_b                   7.8980(10)
_cell_length_c                   14.3767(19)
_cell_measurement_reflns_used    2294
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.76
_cell_measurement_theta_min      2.515
_cell_volume                     1376.9(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7011
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.91
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9791
_exptl_absorpt_correction_T_min  0.9684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0585
_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)+(0.0644P)²+0.3939P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1362
_refine_ls_wR_factor_ref         0.1436
_reflns_number_gt                2061
_reflns_number_total             2429
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo900437p_si_002.cif
_cod_data_source_block           6191m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4024517
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.17901(13) 0.5731(2) -0.03275(12) 0.0614(5) Uani 1 1 d . . .
O2 O 0.53467(11) 0.69450(18) 0.08269(10) 0.0450(4) Uani 1 1 d . . .
N1 N 0.21784(14) 0.4564(2) 0.11863(14) 0.0463(5) Uani 1 1 d . . .
C1 C 0.59190(17) 0.7862(3) 0.02444(16) 0.0447(5) Uani 1 1 d . . .
H1A H 0.6526 0.7200 0.0142 0.054 Uiso 1 1 calc R . .
H1B H 0.6205 0.8925 0.0549 0.054 Uiso 1 1 calc R . .
C2 C 0.50696(18) 0.8161(3) -0.06820(15) 0.0425(5) Uani 1 1 d . . .
C3 C 0.5152(2) 0.9003(3) -0.15054(18) 0.0546(6) Uani 1 1 d . . .
H3 H 0.5818 0.9469 -0.1541 0.066 Uiso 1 1 calc R . .
C4 C 0.4222(2) 0.9129(3) -0.22694(18) 0.0614(7) Uani 1 1 d . . .
H4 H 0.4256 0.9699 -0.2827 0.074 Uiso 1 1 calc R . .
C5 C 0.3238(2) 0.8418(3) -0.22174(17) 0.0587(7) Uani 1 1 d . . .
H5 H 0.2621 0.8514 -0.2744 0.070 Uiso 1 1 calc R . .
C6 C 0.31469(19) 0.7572(3) -0.14068(16) 0.0497(6) Uani 1 1 d . . .
H6 H 0.2481 0.7090 -0.1383 0.060 Uiso 1 1 calc R . .
C7 C 0.40810(18) 0.7456(2) -0.06208(15) 0.0404(5) Uani 1 1 d . . .
C8 C 0.42675(16) 0.6714(2) 0.03412(15) 0.0381(5) Uani 1 1 d . . .
C9 C 0.36295(17) 0.5903(2) 0.08262(15) 0.0394(5) Uani 1 1 d . . .
C10 C 0.39910(17) 0.5241(2) 0.18136(15) 0.0399(5) Uani 1 1 d . . .
C11 C 0.49839(19) 0.5236(3) 0.25270(16) 0.0463(6) Uani 1 1 d . . .
H11 H 0.5597 0.5770 0.2417 0.056 Uiso 1 1 calc R . .
C12 C 0.5068(2) 0.4435(3) 0.34082(17) 0.0520(6) Uani 1 1 d . . .
C13 C 0.4144(2) 0.3657(3) 0.35590(18) 0.0575(7) Uani 1 1 d . . .
H13 H 0.4202 0.3121 0.4147 0.069 Uiso 1 1 calc R . .
C14 C 0.3138(2) 0.3648(3) 0.28696(18) 0.0549(6) Uani 1 1 d . . .
H14 H 0.2524 0.3133 0.2988 0.066 Uiso 1 1 calc R . .
C15 C 0.30791(18) 0.4431(2) 0.19984(16) 0.0435(5) Uani 1 1 d . . .
C16 C 0.24485(18) 0.5446(3) 0.04566(17) 0.0436(5) Uani 1 1 d . . .
C17 C 0.1089(2) 0.3912(3) 0.1127(2) 0.0641(7) Uani 1 1 d . . .
H17A H 0.0761 0.4564 0.1540 0.096 Uiso 1 1 calc R . .
H17B H 0.1143 0.2750 0.1329 0.096 Uiso 1 1 calc R . .
H17C H 0.0639 0.3990 0.0472 0.096 Uiso 1 1 calc R . .
C18 C 0.6159(2) 0.4375(4) 0.4164(2) 0.0759(8) Uani 1 1 d . . .
H18A H 0.6036 0.4310 0.4793 0.114 Uiso 1 1 calc R . .
H18B H 0.6573 0.5379 0.4121 0.114 Uiso 1 1 calc R . .
H18C H 0.6565 0.3397 0.4059 0.114 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 C1 110.90(16) . . ?
C16 N1 C15 111.30(18) . . ?
C16 N1 C17 124.2(2) . . ?
C15 N1 C17 124.5(2) . . ?
O2 C1 C2 104.43(17) . . ?
O2 C1 H1A 110.9 . . ?
C2 C1 H1A 110.9 . . ?
O2 C1 H1B 110.9 . . ?
C2 C1 H1B 110.9 . . ?
H1A C1 H1B 108.9 . . ?
C3 C2 C7 121.5(2) . . ?
C3 C2 C1 129.8(2) . . ?
C7 C2 C1 108.68(19) . . ?
C4 C3 C2 118.1(2) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 121.7(2) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 118.2(2) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
C2 C7 C6 119.7(2) . . ?
C2 C7 C8 107.68(19) . . ?
C6 C7 C8 132.6(2) . . ?
C9 C8 O2 116.56(18) . . ?
C9 C8 C7 135.15(19) . . ?
O2 C8 C7 108.29(17) . . ?
C8 C9 C10 126.42(19) . . ?
C8 C9 C16 127.34(19) . . ?
C10 C9 C16 106.20(18) . . ?
C11 C10 C15 118.7(2) . . ?
C11 C10 C9 134.4(2) . . ?
C15 C10 C9 106.91(18) . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 118.9(2) . . ?
C13 C12 C18 121.0(2) . . ?
C11 C12 C18 120.0(2) . . ?
C14 C13 C12 122.5(2) . . ?
C14 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
C15 C14 C13 117.5(2) . . ?
C15 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
C14 C15 N1 128.7(2) . . ?
C14 C15 C10 122.1(2) . . ?
N1 C15 C10 109.25(19) . . ?
O1 C16 N1 123.3(2) . . ?
O1 C16 C9 130.4(2) . . ?
N1 C16 C9 106.33(19) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C18 H18A 109.5 . . ?
C12 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C12 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
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 C16 1.226(3) . ?
O2 C8 1.362(2) . ?
O2 C1 1.440(2) . ?
N1 C16 1.377(3) . ?
N1 C15 1.394(3) . ?
N1 C17 1.447(3) . ?
C1 C2 1.484(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.386(3) . ?
C2 C7 1.389(3) . ?
C3 C4 1.376(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.396(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.461(3) . ?
C8 C9 1.359(3) . ?
C9 C10 1.465(3) . ?
C9 C16 1.482(3) . ?
C10 C11 1.386(3) . ?
C10 C15 1.402(3) . ?
C11 C12 1.394(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(3) . ?
C12 C18 1.504(3) . ?
C13 C14 1.381(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 O2 C1 C2 -0.9(2) . . . . ?
O2 C1 C2 C3 179.1(2) . . . . ?
O2 C1 C2 C7 0.1(2) . . . . ?
C7 C2 C3 C4 0.2(3) . . . . ?
C1 C2 C3 C4 -178.8(2) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 C7 0.6(4) . . . . ?
C3 C2 C7 C6 0.7(3) . . . . ?
C1 C2 C7 C6 179.91(18) . . . . ?
C3 C2 C7 C8 -178.44(19) . . . . ?
C1 C2 C7 C8 0.7(2) . . . . ?
C5 C6 C7 C2 -1.1(3) . . . . ?
C5 C6 C7 C8 177.9(2) . . . . ?
C1 O2 C8 C9 -178.21(17) . . . . ?
C1 O2 C8 C7 1.4(2) . . . . ?
C2 C7 C8 C9 178.2(2) . . . . ?
C6 C7 C8 C9 -0.9(4) . . . . ?
C2 C7 C8 O2 -1.3(2) . . . . ?
C6 C7 C8 O2 179.7(2) . . . . ?
O2 C8 C9 C10 -0.6(3) . . . . ?
C7 C8 C9 C10 179.9(2) . . . . ?
O2 C8 C9 C16 -177.90(18) . . . . ?
C7 C8 C9 C16 2.7(4) . . . . ?
C8 C9 C10 C11 1.5(4) . . . . ?
C16 C9 C10 C11 179.2(2) . . . . ?
C8 C9 C10 C15 -176.97(19) . . . . ?
C16 C9 C10 C15 0.8(2) . . . . ?
C15 C10 C11 C12 0.2(3) . . . . ?
C9 C10 C11 C12 -178.2(2) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C10 C11 C12 C18 177.6(2) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C18 C12 C13 C14 -178.1(2) . . . . ?
C12 C13 C14 C15 1.0(4) . . . . ?
C13 C14 C15 N1 178.5(2) . . . . ?
C13 C14 C15 C10 -1.2(3) . . . . ?
C16 N1 C15 C14 180.0(2) . . . . ?
C17 N1 C15 C14 2.0(4) . . . . ?
C16 N1 C15 C10 -0.3(2) . . . . ?
C17 N1 C15 C10 -178.3(2) . . . . ?
C11 C10 C15 C14 0.7(3) . . . . ?
C9 C10 C15 C14 179.45(19) . . . . ?
C11 C10 C15 N1 -179.07(18) . . . . ?
C9 C10 C15 N1 -0.3(2) . . . . ?
C15 N1 C16 O1 -179.7(2) . . . . ?
C17 N1 C16 O1 -1.7(3) . . . . ?
C15 N1 C16 C9 0.8(2) . . . . ?
C17 N1 C16 C9 178.74(19) . . . . ?
C8 C9 C16 O1 -2.7(4) . . . . ?
C10 C9 C16 O1 179.6(2) . . . . ?
C8 C9 C16 N1 176.8(2) . . . . ?
C10 C9 C16 N1 -0.9(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658936
