#------------------------------------------------------------------------------
#$Date: 2020-04-04 07:28:42 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250109 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/81/4038111.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_4038111
loop_
_publ_author_name
'Parveen, Naziya'
'Sekar, Govindasamy'
_publ_section_title
;
 Palladium Nanoparticle-Catalyzed Stereoselective Domino Synthesis of
 3-Allylidene-2(3H)-oxindoles and
 3-Allylidene-2(3H)-benzofuranones.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4682
_journal_page_last               4694
_journal_paper_doi               10.1021/acs.joc.9b03397
_journal_volume                  85
_journal_year                    2020
_chemical_formula_sum            'C24 H19 N O2'
_chemical_formula_weight         353.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.613(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2530(6)
_cell_length_b                   8.2293(3)
_cell_length_c                   16.3693(8)
_cell_measurement_reflns_used    6323
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.57
_cell_measurement_theta_min      2.52
_cell_volume                     1898.34(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14458
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.982
_diffrn_reflns_theta_max         24.982
_diffrn_reflns_theta_min         1.768
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       Block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0105(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0407P)²+0.5137P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1049
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2645
_reflns_number_total             3339
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03397_si_002.cif
_cod_data_source_block           18
_cod_depositor_comments
'Adding full bibliography for 4038109--4038113.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038111
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.981
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.26060(10) -0.2250(2) 0.47544(10) 0.0496(4) Uani 1 1 d . . . . .
C2 C 0.17040(11) -0.1632(2) 0.47786(11) 0.0617(5) Uani 1 1 d . . . . .
H2 H 0.1525 -0.0637 0.4535 0.074 Uiso 1 1 calc R U . . .
C3 C 0.10727(13) -0.2517(3) 0.51702(13) 0.0730(6) Uani 1 1 d . . . . .
H3 H 0.0468 -0.2108 0.5187 0.088 Uiso 1 1 calc R U . . .
C4 C 0.13270(13) -0.3989(3) 0.55331(13) 0.0739(6) Uani 1 1 d . . . . .
H4 H 0.0889 -0.4569 0.5785 0.089 Uiso 1 1 calc R U . . .
C5 C 0.22269(13) -0.4622(2) 0.55295(12) 0.0669(5) Uani 1 1 d . . . . .
H5 H 0.2404 -0.5612 0.5780 0.080 Uiso 1 1 calc R U . . .
C6 C 0.28506(11) -0.3732(2) 0.51422(10) 0.0536(4) Uani 1 1 d . . . . .
C7 C 0.41962(11) -0.2919(2) 0.46624(10) 0.0507(4) Uani 1 1 d . . . . .
C8 C 0.34462(10) -0.16541(19) 0.44271(10) 0.0467(4) Uani 1 1 d . . . . .
C9 C 0.35459(10) -0.03101(19) 0.39653(9) 0.0461(4) Uani 1 1 d . . . . .
C10 C 0.44350(10) 0.01803(19) 0.37174(10) 0.0491(4) Uani 1 1 d . . . . .
H10 H 0.4988 -0.0310 0.3978 0.059 Uiso 1 1 calc R U . . .
C11 C 0.45124(11) 0.12939(19) 0.31370(10) 0.0500(4) Uani 1 1 d . . . . .
H11 H 0.3959 0.1831 0.2913 0.060 Uiso 1 1 calc R U . . .
C12 C 0.53757(11) 0.17496(18) 0.28206(10) 0.0469(4) Uani 1 1 d . . . . .
C13 C 0.62714(11) 0.1329(2) 0.32156(10) 0.0539(4) Uani 1 1 d . . . . .
H13 H 0.6329 0.0798 0.3722 0.065 Uiso 1 1 calc R U . . .
C14 C 0.70792(11) 0.1675(2) 0.28794(11) 0.0560(4) Uani 1 1 d . . . . .
H14 H 0.7672 0.1382 0.3158 0.067 Uiso 1 1 calc R U . . .
C15 C 0.70051(11) 0.24545(19) 0.21308(11) 0.0513(4) Uani 1 1 d . . . . .
C16 C 0.61254(12) 0.2927(2) 0.17327(12) 0.0622(5) Uani 1 1 d . . . . .
H16 H 0.6075 0.3480 0.1232 0.075 Uiso 1 1 calc R U . . .
C17 C 0.53243(12) 0.2582(2) 0.20734(11) 0.0592(5) Uani 1 1 d . . . . .
H17 H 0.4736 0.2911 0.1800 0.071 Uiso 1 1 calc R U . . .
C18 C 0.86653(13) 0.2240(3) 0.21058(14) 0.0853(7) Uani 1 1 d . . . . .
H18A H 0.8836 0.2766 0.2631 0.128 Uiso 1 1 calc R U . . .
H18B H 0.9128 0.2494 0.1755 0.128 Uiso 1 1 calc R U . . .
H18C H 0.8645 0.1086 0.2185 0.128 Uiso 1 1 calc R U . . .
C19 C 0.26945(10) 0.06928(19) 0.36532(10) 0.0481(4) Uani 1 1 d . . . . .
C20 C 0.25123(13) 0.2129(2) 0.40288(13) 0.0727(6) Uani 1 1 d . . . . .
H20 H 0.2929 0.2497 0.4483 0.087 Uiso 1 1 calc R U . . .
C21 C 0.17145(14) 0.3030(3) 0.37361(17) 0.0882(7) Uani 1 1 d . . . . .
H21 H 0.1592 0.3988 0.4002 0.106 Uiso 1 1 calc R U . . .
C22 C 0.11098(14) 0.2529(3) 0.30653(16) 0.0809(7) Uani 1 1 d . . . . .
H22 H 0.0572 0.3139 0.2874 0.097 Uiso 1 1 calc R U . . .
C23 C 0.12910(13) 0.1126(3) 0.26704(13) 0.0762(6) Uani 1 1 d . . . . .
H23 H 0.0882 0.0791 0.2204 0.091 Uiso 1 1 calc R U . . .
C24 C 0.20836(12) 0.0202(2) 0.29645(11) 0.0623(5) Uani 1 1 d . . . . .
H24 H 0.2203 -0.0754 0.2695 0.075 Uiso 1 1 calc R U . . .
N1 N 0.37916(10) -0.41052(19) 0.50716(10) 0.0579(4) Uani 1 1 d . . . . .
O1 O 0.50145(8) -0.29779(14) 0.45060(8) 0.0626(3) Uani 1 1 d . . . . .
O2 O 0.77580(8) 0.27966(15) 0.17307(8) 0.0652(4) Uani 1 1 d . . . . .
H1N H 0.4104(13) -0.502(2) 0.5259(12) 0.077(6) 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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.47(15) . . ?
C2 C1 C8 134.22(16) . . ?
C6 C1 C8 107.24(13) . . ?
C3 C2 C1 119.23(18) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C4 C3 C2 121.03(18) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.94(17) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 117.65(18) . . ?
C6 C5 H5 121.2 . . ?
C4 C5 H5 121.2 . . ?
C5 C6 C1 122.66(16) . . ?
C5 C6 N1 127.94(17) . . ?
C1 C6 N1 109.39(14) . . ?
O1 C7 N1 123.96(15) . . ?
O1 C7 C8 129.36(15) . . ?
N1 C7 C8 106.62(13) . . ?
C9 C8 C1 129.35(14) . . ?
C9 C8 C7 125.28(13) . . ?
C1 C8 C7 105.26(13) . . ?
C8 C9 C10 123.55(14) . . ?
C8 C9 C19 119.53(13) . . ?
C10 C9 C19 116.85(14) . . ?
C11 C10 C9 124.09(15) . . ?
C11 C10 H10 118.0 . . ?
C9 C10 H10 118.0 . . ?
C10 C11 C12 126.48(15) . . ?
C10 C11 H11 116.8 . . ?
C12 C11 H11 116.8 . . ?
C13 C12 C17 117.11(14) . . ?
C13 C12 C11 122.61(15) . . ?
C17 C12 C11 120.22(14) . . ?
C14 C13 C12 121.90(16) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C15 C14 C13 119.72(15) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
O2 C15 C14 124.24(15) . . ?
O2 C15 C16 116.01(15) . . ?
C14 C15 C16 119.75(15) . . ?
C17 C16 C15 120.14(16) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C12 121.34(16) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C24 118.64(16) . . ?
C20 C19 C9 121.36(15) . . ?
C24 C19 C9 119.98(15) . . ?
C19 C20 C21 120.45(19) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 120.6(2) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 119.87(19) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C22 C23 C24 120.05(19) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C19 C24 C23 120.37(19) . . ?
C19 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C7 N1 C6 111.47(14) . . ?
C7 N1 H1N 122.8(12) . . ?
C6 N1 H1N 125.7(12) . . ?
C15 O2 C18 117.07(15) . . ?
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
C1 C2 1.389(2) . ?
C1 C6 1.395(2) . ?
C1 C8 1.468(2) . ?
C2 C3 1.387(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(2) . ?
C5 H5 0.9300 . ?
C6 N1 1.397(2) . ?
C7 O1 1.2320(18) . ?
C7 N1 1.360(2) . ?
C7 C8 1.500(2) . ?
C8 C9 1.359(2) . ?
C9 C10 1.445(2) . ?
C9 C19 1.493(2) . ?
C10 C11 1.336(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.454(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(2) . ?
C12 C17 1.394(2) . ?
C13 C14 1.378(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(2) . ?
C14 H14 0.9300 . ?
C15 O2 1.3676(18) . ?
C15 C16 1.380(2) . ?
C16 C17 1.373(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O2 1.422(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.375(2) . ?
C19 C24 1.378(2) . ?
C20 C21 1.382(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.355(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.366(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.387(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
N1 H1N 0.908(19) . ?
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
C6 C1 C2 C3 -1.3(3) . . . . ?
C8 C1 C2 C3 -177.91(18) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C5 C6 N1 178.83(17) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
C8 C1 C6 C5 179.07(16) . . . . ?
C2 C1 C6 N1 -177.92(15) . . . . ?
C8 C1 C6 N1 -0.45(18) . . . . ?
C2 C1 C8 C9 -6.9(3) . . . . ?
C6 C1 C8 C9 176.21(16) . . . . ?
C2 C1 C8 C7 176.73(18) . . . . ?
C6 C1 C8 C7 -0.16(17) . . . . ?
O1 C7 C8 C9 1.4(3) . . . . ?
N1 C7 C8 C9 -175.83(15) . . . . ?
O1 C7 C8 C1 177.95(17) . . . . ?
N1 C7 C8 C1 0.73(17) . . . . ?
C1 C8 C9 C10 176.76(15) . . . . ?
C7 C8 C9 C10 -7.5(2) . . . . ?
C1 C8 C9 C19 -6.4(3) . . . . ?
C7 C8 C9 C19 169.32(15) . . . . ?
C8 C9 C10 C11 166.23(16) . . . . ?
C19 C9 C10 C11 -10.7(2) . . . . ?
C9 C10 C11 C12 -175.20(15) . . . . ?
C10 C11 C12 C13 -14.7(3) . . . . ?
C10 C11 C12 C17 162.41(17) . . . . ?
C17 C12 C13 C14 -1.7(3) . . . . ?
C11 C12 C13 C14 175.57(15) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 O2 -177.38(15) . . . . ?
C13 C14 C15 C16 1.9(3) . . . . ?
O2 C15 C16 C17 177.67(16) . . . . ?
C14 C15 C16 C17 -1.7(3) . . . . ?
C15 C16 C17 C12 -0.3(3) . . . . ?
C13 C12 C17 C16 1.9(3) . . . . ?
C11 C12 C17 C16 -175.40(16) . . . . ?
C8 C9 C19 C20 101.8(2) . . . . ?
C10 C9 C19 C20 -81.1(2) . . . . ?
C8 C9 C19 C24 -79.6(2) . . . . ?
C10 C9 C19 C24 97.41(18) . . . . ?
C24 C19 C20 C21 2.2(3) . . . . ?
C9 C19 C20 C21 -179.25(19) . . . . ?
C19 C20 C21 C22 -1.3(4) . . . . ?
C20 C21 C22 C23 -0.4(4) . . . . ?
C21 C22 C23 C24 1.1(3) . . . . ?
C20 C19 C24 C23 -1.4(3) . . . . ?
C9 C19 C24 C23 180.00(16) . . . . ?
C22 C23 C24 C19 -0.2(3) . . . . ?
O1 C7 N1 C6 -178.45(16) . . . . ?
C8 C7 N1 C6 -1.04(19) . . . . ?
C5 C6 N1 C7 -178.51(18) . . . . ?
C1 C6 N1 C7 1.0(2) . . . . ?
C14 C15 O2 C18 2.8(3) . . . . ?
C16 C15 O2 C18 -176.53(17) . . . . ?
