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#$Date: 2024-09-06 04:57:06 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294634 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/00/7160064.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_7160064
loop_
_publ_author_name
'Sarmah, Debasish'
'Choudhury, Anup'
'Bora, Utpal'
_publ_section_title
;
 Palladium nanoparticle catalyzed synthesis of indoles via
 intramolecular Heck cyclisation.
;
_journal_issue                   31
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6419
_journal_page_last               6431
_journal_paper_doi               10.1039/d4ob01177e
_journal_volume                  22
_journal_year                    2024
_chemical_formula_sum            'C12 H11 N O4'
_chemical_formula_weight         233.22
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2023-10-05 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   33.45(2)
_cell_length_b                   33.45(2)
_cell_length_c                   5.541(4)
_cell_measurement_reflns_used    997
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      13.62
_cell_measurement_theta_min      3.65
_cell_volume                     5369(6)
_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-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.2469
_diffrn_reflns_av_unetI/netI     0.0831
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            51845
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         3.655
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       Needle
_exptl_crystal_F_000             2196
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       0.0021(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.1260
_refine_ls_R_factor_gt           0.0781
_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)+(0.1377P)²+6.2532P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2172
_refine_ls_wR_factor_ref         0.2473
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1481
_reflns_number_total             2342
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01177e2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7160064.cif.'
_cod_original_cell_volume        5369(7)
_cod_database_code               7160064
_shelx_shelxl_version_number     2017/1
_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   0.971
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
O1 O 0.17584(12) 0.08729(15) 0.2707(7) 0.0789(14) Uani 1 1 d . . . . .
O2 O 0.20036(9) 0.05849(10) 0.5540(5) 0.0420(8) Uani 1 1 d . . . . .
O3 O 0.28031(9) 0.16673(8) -0.3181(4) 0.0310(7) Uani 1 1 d . . . . .
O4 O 0.21905(9) 0.14815(9) -0.0838(5) 0.0370(8) Uani 1 1 d . . . . .
N1 N 0.31064(11) 0.12363(10) -0.0235(6) 0.0264(8) Uani 1 1 d . . . . .
C1 C 0.35685(14) 0.09122(13) 0.1567(6) 0.0296(9) Uani 1 1 d . . . . .
H1 H 0.380425 0.103555 0.042873 0.035 Uiso 1 1 calc R U . . .
C2 C 0.35715(13) 0.06488(12) 0.3457(7) 0.0314(9) Uani 1 1 d . . . . .
H2 H 0.381382 0.058910 0.359929 0.038 Uiso 1 1 calc R U . . .
C3 C 0.32164(13) 0.04675(13) 0.5179(6) 0.0302(9) Uani 1 1 d . . . . .
H3 H 0.323308 0.029524 0.645212 0.036 Uiso 1 1 calc R U . . .
C4 C 0.28442(13) 0.05360(12) 0.5047(6) 0.0288(9) Uani 1 1 d . . . . .
H4 H 0.261116 0.041114 0.619979 0.035 Uiso 1 1 calc R U . . .
C5 C 0.28257(13) 0.08023(12) 0.3104(6) 0.0267(9) Uani 1 1 d . . . . .
C6 C 0.31915(13) 0.09859(12) 0.1441(6) 0.0264(9) Uani 1 1 d . . . . .
C7 C 0.25047(13) 0.09474(12) 0.2343(6) 0.0271(9) Uani 1 1 d . . . . .
C8 C 0.26983(12) 0.12176(12) 0.0275(6) 0.0254(8) Uani 1 1 d . . . . .
C9 C 0.20578(14) 0.08179(14) 0.3465(6) 0.0325(9) Uani 1 1 d . . . . .
C10 C 0.20500(15) 0.17192(15) -0.2499(8) 0.0440(11) Uani 1 1 d . . . . .
H10A H 0.177187 0.170369 -0.192482 0.066 Uiso 1 1 calc R U . . .
H10B H 0.228936 0.203631 -0.262206 0.066 Uiso 1 1 calc R U . . .
H10C H 0.199521 0.157599 -0.405860 0.066 Uiso 1 1 calc R U . . .
C11 C 0.15625(14) 0.04061(15) 0.6724(8) 0.0457(12) Uani 1 1 d . . . . .
H11A H 0.156003 0.024743 0.817210 0.069 Uiso 1 1 calc R U . . .
H11B H 0.151168 0.065647 0.712277 0.069 Uiso 1 1 calc R U . . .
H11C H 0.132221 0.019535 0.566292 0.069 Uiso 1 1 calc R U . . .
C12 C 0.25720(12) 0.14763(12) -0.1416(6) 0.0268(9) Uani 1 1 d . . . . .
H11 H 0.3294(17) 0.1380(15) -0.157(8) 0.053(13) 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'
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'
H H 0.0000 0.0000 '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
C9 O2 C11 116.2(3) . . ?
C12 O4 C10 115.8(3) . . ?
C8 N1 C6 109.9(3) . . ?
C2 C1 C6 116.6(4) . . ?
C1 C2 C3 121.3(4) . . ?
C4 C3 C2 122.2(3) . . ?
C3 C4 C5 118.2(4) . . ?
C6 C5 C4 118.1(3) . . ?
C6 C5 C7 107.0(3) . . ?
C4 C5 C7 134.9(3) . . ?
N1 C6 C1 128.3(3) . . ?
N1 C6 C5 108.0(3) . . ?
C1 C6 C5 123.6(3) . . ?
C8 C7 C5 105.9(3) . . ?
C8 C7 C9 127.6(3) . . ?
C5 C7 C9 126.5(3) . . ?
N1 C8 C7 109.2(3) . . ?
N1 C8 C12 114.5(3) . . ?
C7 C8 C12 136.3(3) . . ?
O1 C9 O2 120.9(4) . . ?
O1 C9 C7 128.3(4) . . ?
O2 C9 C7 110.7(3) . . ?
O3 C12 O4 123.6(3) . . ?
O3 C12 C8 121.9(3) . . ?
O4 C12 C8 114.5(3) . . ?
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 C9 1.182(5) . ?
O2 C9 1.350(4) . ?
O2 C11 1.443(5) . ?
O3 C12 1.212(4) . ?
O4 C12 1.324(4) . ?
O4 C10 1.440(5) . ?
N1 C8 1.364(5) . ?
N1 C6 1.372(4) . ?
C1 C2 1.372(5) . ?
C1 C6 1.403(5) . ?
C2 C3 1.403(5) . ?
C3 C4 1.376(5) . ?
C4 C5 1.418(5) . ?
C5 C6 1.404(5) . ?
C5 C7 1.445(5) . ?
C7 C8 1.401(5) . ?
C7 C9 1.470(5) . ?
C8 C12 1.474(5) . ?
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 -0.6(5) . . . . ?
C1 C2 C3 C4 1.2(6) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
C3 C4 C5 C7 179.8(4) . . . . ?
C8 N1 C6 C1 179.3(3) . . . . ?
C8 N1 C6 C5 -0.5(4) . . . . ?
C2 C1 C6 N1 179.5(3) . . . . ?
C2 C1 C6 C5 -0.7(5) . . . . ?
C4 C5 C6 N1 -178.7(3) . . . . ?
C7 C5 C6 N1 0.8(4) . . . . ?
C4 C5 C6 C1 1.4(5) . . . . ?
C7 C5 C6 C1 -179.0(3) . . . . ?
C6 C5 C7 C8 -0.9(4) . . . . ?
C4 C5 C7 C8 178.6(4) . . . . ?
C6 C5 C7 C9 176.7(3) . . . . ?
C4 C5 C7 C9 -3.9(6) . . . . ?
C6 N1 C8 C7 -0.1(4) . . . . ?
C6 N1 C8 C12 179.9(3) . . . . ?
C5 C7 C8 N1 0.6(4) . . . . ?
C9 C7 C8 N1 -176.9(3) . . . . ?
C5 C7 C8 C12 -179.4(4) . . . . ?
C9 C7 C8 C12 3.1(7) . . . . ?
C11 O2 C9 O1 0.8(6) . . . . ?
C11 O2 C9 C7 -175.3(3) . . . . ?
C8 C7 C9 O1 9.0(7) . . . . ?
C5 C7 C9 O1 -168.0(4) . . . . ?
C8 C7 C9 O2 -175.2(3) . . . . ?
C5 C7 C9 O2 7.8(5) . . . . ?
C10 O4 C12 O3 2.0(5) . . . . ?
C10 O4 C12 C8 -178.1(3) . . . . ?
N1 C8 C12 O3 3.8(5) . . . . ?
C7 C8 C12 O3 -176.2(4) . . . . ?
N1 C8 C12 O4 -176.1(3) . . . . ?
C7 C8 C12 O4 3.9(6) . . . . ?
