#------------------------------------------------------------------------------
#$Date: 2020-04-04 07:28:42 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250109 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/81/4038110.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_4038110
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_moiety         'C21 H19 N O3'
_chemical_formula_sum            'C21 H19 N O3'
_chemical_formula_weight         333.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 102.5359(17)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.5819(9)
_cell_length_b                   12.8776(5)
_cell_length_c                   13.9465(6)
_cell_measurement_reflns_used    3115
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.29
_cell_measurement_theta_min      2.53
_cell_volume                     3608.3(3)
_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  0.0307
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10809
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.878
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       Block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0014(3)
_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   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0710P)²+0.8493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1414
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2115
_reflns_number_total             3187
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03397_si_002.cif
_cod_data_source_block           8
_cod_depositor_comments
'Adding full bibliography for 4038109--4038113.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4038110
_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   0.977
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_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_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 0.84660(9) -0.18918(16) 0.09485(15) 0.0552(6) Uani 1 1 d . . . . .
H1 H 0.8134 -0.1391 0.0878 0.066 Uiso 1 1 calc R U . . .
C2 C 0.83055(11) -0.29397(18) 0.09261(17) 0.0673(6) Uani 1 1 d . . . . .
H2 H 0.7863 -0.3141 0.0841 0.081 Uiso 1 1 calc R U . . .
C3 C 0.87952(13) -0.36823(18) 0.10288(17) 0.0717(7) Uani 1 1 d . . . . .
H3 H 0.8676 -0.4380 0.1007 0.086 Uiso 1 1 calc R U . . .
C4 C 0.94597(12) -0.34200(16) 0.11641(17) 0.0634(6) Uani 1 1 d . . . . .
H4 H 0.9790 -0.3926 0.1240 0.076 Uiso 1 1 calc R U . . .
C5 C 0.96130(10) -0.23807(15) 0.11813(14) 0.0480(5) Uani 1 1 d . . . . .
C6 C 1.02056(9) -0.08712(16) 0.12976(13) 0.0445(5) Uani 1 1 d . . . . .
C7 C 0.94751(8) -0.05985(14) 0.11441(13) 0.0403(5) Uani 1 1 d . . . . .
C8 C 0.91271(9) -0.16017(15) 0.10766(13) 0.0436(5) Uani 1 1 d . . . . .
C9 C 0.92302(8) 0.03769(14) 0.10920(13) 0.0415(5) Uani 1 1 d . . . . .
C10 C 0.96551(9) 0.12925(15) 0.12038(14) 0.0467(5) Uani 1 1 d . . . . .
H10 H 1.0113 0.1193 0.1333 0.056 Uiso 1 1 calc R U . . .
C11 C 0.94279(10) 0.22604(16) 0.11317(15) 0.0538(5) Uani 1 1 d . . . . .
H11 H 0.8969 0.2354 0.1014 0.065 Uiso 1 1 calc R U . . .
C12 C 0.98445(12) 0.31902(18) 0.12238(17) 0.0624(6) Uani 1 1 d . . . . .
C13 C 1.09497(14) 0.3850(2) 0.1591(2) 0.0852(8) Uani 1 1 d . . . . .
H13A H 1.0883 0.4309 0.2113 0.102 Uiso 1 1 calc R U . . .
H13B H 1.0880 0.4244 0.0984 0.102 Uiso 1 1 calc R U . . .
C14 C 1.16337(14) 0.3409(3) 0.1827(2) 0.1128(11) Uani 1 1 d . . . . .
H14A H 1.1706 0.3059 0.2449 0.169 Uiso 1 1 calc R U . . .
H14B H 1.1953 0.3959 0.1859 0.169 Uiso 1 1 calc R U . . .
H14C H 1.1684 0.2924 0.1325 0.169 Uiso 1 1 calc R U . . .
C15 C 1.08641(10) -0.24993(19) 0.14451(16) 0.0665(6) Uani 1 1 d . . . . .
H15A H 1.1229 -0.2019 0.1533 0.100 Uiso 1 1 calc R U . . .
H15B H 1.0861 -0.2919 0.0875 0.100 Uiso 1 1 calc R U . . .
H15C H 1.0914 -0.2937 0.2013 0.100 Uiso 1 1 calc R U . . .
C16 C 0.84979(9) 0.05644(14) 0.09007(15) 0.0445(5) Uani 1 1 d . . . . .
C17 C 0.81296(9) 0.05851(17) -0.00553(16) 0.0577(6) Uani 1 1 d . . . . .
H17 H 0.8337 0.0462 -0.0574 0.069 Uiso 1 1 calc R U . . .
C18 C 0.74554(10) 0.07877(19) -0.0243(2) 0.0724(7) Uani 1 1 d . . . . .
H18 H 0.7211 0.0799 -0.0888 0.087 Uiso 1 1 calc R U . . .
C19 C 0.71470(11) 0.0970(2) 0.0504(2) 0.0796(8) Uani 1 1 d . . . . .
H19 H 0.6692 0.1102 0.0371 0.095 Uiso 1 1 calc R U . . .
C20 C 0.75024(12) 0.0963(2) 0.1452(2) 0.0808(8) Uani 1 1 d . . . . .
H20 H 0.7289 0.1091 0.1963 0.097 Uiso 1 1 calc R U . . .
C21 C 0.81813(10) 0.07638(18) 0.16567(17) 0.0630(6) Uani 1 1 d . . . . .
H21 H 0.8422 0.0765 0.2303 0.076 Uiso 1 1 calc R U . . .
N1 N 1.02437(8) -0.19301(13) 0.13150(11) 0.0501(4) Uani 1 1 d . . . . .
O1 O 1.06894(6) -0.02994(12) 0.13908(10) 0.0594(4) Uani 1 1 d . . . . .
O2 O 0.96251(10) 0.40507(13) 0.10683(16) 0.1019(7) Uani 1 1 d . . . . .
O3 O 1.04913(8) 0.29854(12) 0.14889(11) 0.0706(5) Uani 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
C8 C1 C2 119.19(19) . . ?
C8 C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 121.7(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 117.2(2) . . ?
C5 C4 H4 121.4 . . ?
C3 C4 H4 121.4 . . ?
C4 C5 N1 127.60(18) . . ?
C4 C5 C8 122.64(19) . . ?
N1 C5 C8 109.75(17) . . ?
O1 C6 N1 123.85(17) . . ?
O1 C6 C7 129.54(18) . . ?
N1 C6 C7 106.60(16) . . ?
C9 C7 C8 130.04(16) . . ?
C9 C7 C6 124.86(17) . . ?
C8 C7 C6 105.10(15) . . ?
C1 C8 C5 118.64(18) . . ?
C1 C8 C7 134.17(17) . . ?
C5 C8 C7 107.19(16) . . ?
C7 C9 C10 122.63(16) . . ?
C7 C9 C16 120.74(16) . . ?
C10 C9 C16 116.62(16) . . ?
C11 C10 C9 123.97(18) . . ?
C11 C10 H10 118.0 . . ?
C9 C10 H10 118.0 . . ?
C10 C11 C12 124.9(2) . . ?
C10 C11 H11 117.6 . . ?
C12 C11 H11 117.6 . . ?
O2 C12 O3 123.3(2) . . ?
O2 C12 C11 123.4(2) . . ?
O3 C12 C11 113.3(2) . . ?
O3 C13 C14 107.1(2) . . ?
O3 C13 H13A 110.3 . . ?
C14 C13 H13A 110.3 . . ?
O3 C13 H13B 110.3 . . ?
C14 C13 H13B 110.3 . . ?
H13A C13 H13B 108.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 118.85(18) . . ?
C21 C16 C9 121.34(17) . . ?
C17 C16 C9 119.75(17) . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 120.1(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C21 120.3(2) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 119.9(2) . . ?
C16 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C6 N1 C5 111.35(15) . . ?
C6 N1 C15 123.57(17) . . ?
C5 N1 C15 125.07(18) . . ?
C12 O3 C13 117.87(19) . . ?
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 C8 1.385(3) . ?
C1 C2 1.388(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.397(2) . ?
C5 C8 1.402(3) . ?
C6 O1 1.223(2) . ?
C6 N1 1.366(3) . ?
C6 C7 1.513(2) . ?
C7 C9 1.350(2) . ?
C7 C8 1.470(3) . ?
C9 C10 1.456(3) . ?
C9 C16 1.492(2) . ?
C10 C11 1.327(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.462(3) . ?
C11 H11 0.9300 . ?
C12 O2 1.199(3) . ?
C12 O3 1.329(3) . ?
C13 O3 1.446(3) . ?
C13 C14 1.487(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N1 1.449(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C21 1.379(3) . ?
C16 C17 1.383(3) . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.353(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.365(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.388(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
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 C1 C2 C3 0.0(3) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 N1 179.42(19) . . . . ?
C3 C4 C5 C8 0.5(3) . . . . ?
O1 C6 C7 C9 -0.7(3) . . . . ?
N1 C6 C7 C9 179.48(17) . . . . ?
O1 C6 C7 C8 179.59(19) . . . . ?
N1 C6 C7 C8 -0.25(18) . . . . ?
C2 C1 C8 C5 -0.1(3) . . . . ?
C2 C1 C8 C7 -179.4(2) . . . . ?
C4 C5 C8 C1 -0.1(3) . . . . ?
N1 C5 C8 C1 -179.20(16) . . . . ?
C4 C5 C8 C7 179.34(18) . . . . ?
N1 C5 C8 C7 0.3(2) . . . . ?
C9 C7 C8 C1 -0.4(4) . . . . ?
C6 C7 C8 C1 179.3(2) . . . . ?
C9 C7 C8 C5 -179.73(19) . . . . ?
C6 C7 C8 C5 -0.02(19) . . . . ?
C8 C7 C9 C10 178.15(17) . . . . ?
C6 C7 C9 C10 -1.5(3) . . . . ?
C8 C7 C9 C16 -2.7(3) . . . . ?
C6 C7 C9 C16 177.67(16) . . . . ?
C7 C9 C10 C11 178.24(19) . . . . ?
C16 C9 C10 C11 -1.0(3) . . . . ?
C9 C10 C11 C12 -178.86(19) . . . . ?
C10 C11 C12 O2 173.0(2) . . . . ?
C10 C11 C12 O3 -6.4(3) . . . . ?
C7 C9 C16 C21 97.8(2) . . . . ?
C10 C9 C16 C21 -83.0(2) . . . . ?
C7 C9 C16 C17 -85.1(2) . . . . ?
C10 C9 C16 C17 94.1(2) . . . . ?
C21 C16 C17 C18 -0.9(3) . . . . ?
C9 C16 C17 C18 -178.11(19) . . . . ?
C16 C17 C18 C19 0.1(4) . . . . ?
C17 C18 C19 C20 0.4(4) . . . . ?
C18 C19 C20 C21 -0.2(4) . . . . ?
C17 C16 C21 C20 1.1(3) . . . . ?
C9 C16 C21 C20 178.3(2) . . . . ?
C19 C20 C21 C16 -0.6(4) . . . . ?
O1 C6 N1 C5 -179.42(18) . . . . ?
C7 C6 N1 C5 0.4(2) . . . . ?
O1 C6 N1 C15 -0.1(3) . . . . ?
C7 C6 N1 C15 179.78(16) . . . . ?
C4 C5 N1 C6 -179.5(2) . . . . ?
C8 C5 N1 C6 -0.5(2) . . . . ?
C4 C5 N1 C15 1.2(3) . . . . ?
C8 C5 N1 C15 -179.80(17) . . . . ?
O2 C12 O3 C13 -0.1(3) . . . . ?
C11 C12 O3 C13 179.30(19) . . . . ?
C14 C13 O3 C12 -176.5(2) . . . . ?
