#------------------------------------------------------------------------------
#$Date: 2025-01-06 15:50:49 +0200 (Mon, 06 Jan 2025) $
#$Revision: 297132 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160184.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_7160184
loop_
_publ_author_name
'Prabhakaran, Mohan'
'Sanjana, Ramesh'
'Parthasarathy, Kanniyappan'
_publ_section_title
;
 Ruthenium-catalyzed Heck coupling of 3-arylidene-oxindoles with alkenes:
 a facile synthesis of 3-allylidene-2(3H)-oxindoles.
;
_journal_issue                   48
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9348
_journal_page_last               9352
_journal_paper_doi               10.1039/d4ob01072h
_journal_volume                  22
_journal_year                    2024
_chemical_formula_sum            'C20 H16 N O3'
_chemical_formula_weight         318.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-08-24 deposited with the CCDC.	2024-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                119.1405(13)
_cell_angle_beta                 91.334(2)
_cell_angle_gamma                97.5234(17)
_cell_formula_units_Z            2
_cell_length_a                   9.5665(4)
_cell_length_b                   9.9423(4)
_cell_length_c                   10.1434(6)
_cell_measurement_reflns_used    5875
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.09
_cell_measurement_theta_min      2.36
_cell_volume                     831.17(7)
_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 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  0.0167
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10941
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.158
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       Block
_exptl_crystal_F_000             334
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2912
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0454
_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)+(0.0726P)²+0.2461P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1309
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2459
_reflns_number_total             2912
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01072h2.cif
_cod_data_source_block           33
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7160184.cif.
;
_cod_database_code               7160184
_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   0.973
_shelx_estimated_absorpt_t_max   0.986
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.28459(17) 0.55250(19) 1.23024(18) 0.0406(4) Uani 1 1 d . . . . .
C2 C 0.2679(2) 0.6361(2) 1.3823(2) 0.0518(5) Uani 1 1 d . . . . .
H2 H 0.3043 0.6099 1.4510 0.062 Uiso 1 1 calc R U . . .
C3 C 0.1951(2) 0.7603(2) 1.4292(2) 0.0597(5) Uani 1 1 d . . . . .
H3 H 0.1836 0.8200 1.5316 0.072 Uiso 1 1 calc R U . . .
C4 C 0.1391(2) 0.7973(2) 1.3267(2) 0.0598(5) Uani 1 1 d . . . . .
H4 H 0.0872 0.8789 1.3604 0.072 Uiso 1 1 calc R U . . .
C5 C 0.1590(2) 0.7148(2) 1.1745(2) 0.0507(5) Uani 1 1 d . . . . .
H5 H 0.1217 0.7412 1.1063 0.061 Uiso 1 1 calc R U . . .
C6 C 0.23524(17) 0.59241(19) 1.12480(18) 0.0385(4) Uani 1 1 d . . . . .
C7 C 0.27680(16) 0.48221(18) 0.97696(18) 0.0361(4) Uani 1 1 d . . . . .
C8 C 0.34519(17) 0.36736(19) 1.00389(18) 0.0398(4) Uani 1 1 d . . . . .
C9 C 0.26827(16) 0.48344(18) 0.84326(18) 0.0364(4) Uani 1 1 d . . . . .
C10 C 0.21408(17) 0.61350(18) 0.83478(17) 0.0372(4) Uani 1 1 d . . . . .
C11 C 0.29745(19) 0.7595(2) 0.8960(2) 0.0463(4) Uani 1 1 d . . . . .
H11 H 0.3883 0.7763 0.9416 0.056 Uiso 1 1 calc R U . . .
C12 C 0.2461(2) 0.8803(2) 0.8897(2) 0.0539(5) Uani 1 1 d . . . . .
H12 H 0.3032 0.9775 0.9314 0.065 Uiso 1 1 calc R U . . .
C13 C 0.1118(2) 0.8596(2) 0.8228(2) 0.0544(5) Uani 1 1 d . . . . .
C14 C 0.0303(2) 0.7135(3) 0.7607(2) 0.0616(5) Uani 1 1 d . . . . .
H14 H -0.0603 0.6968 0.7146 0.074 Uiso 1 1 calc R U . . .
C15 C 0.08049(19) 0.5910(2) 0.7654(2) 0.0519(5) Uani 1 1 d . . . . .
H15 H 0.0239 0.4933 0.7218 0.062 Uiso 1 1 calc R U . . .
C16 C 0.0556(3) 0.9927(3) 0.8182(3) 0.0849(8) Uani 1 1 d . . . . .
H16A H 0.0529 1.0754 0.9199 0.127 Uiso 1 1 calc R U . . .
H16B H -0.0383 0.9564 0.7664 0.127 Uiso 1 1 calc R U . . .
H16C H 0.1165 1.0307 0.7655 0.127 Uiso 1 1 calc R U . . .
C17 C 0.31516(17) 0.36308(19) 0.70629(18) 0.0401(4) Uani 1 1 d . . . . .
H17 H 0.3442 0.2790 0.7095 0.048 Uiso 1 1 calc R U . . .
C18 C 0.3190(2) 0.3659(2) 0.57704(19) 0.0487(4) Uani 1 1 d . . . . .
H18 H 0.2846 0.4472 0.5730 0.058 Uiso 1 1 calc R U . . .
C19 C 0.3732(2) 0.2509(2) 0.44015(19) 0.0490(4) Uani 1 1 d . . . . .
C20 C 0.4652(3) 0.0155(2) 0.3203(2) 0.0653(6) Uani 1 1 d . . . . .
H20A H 0.4045 -0.0201 0.2291 0.098 Uiso 1 1 calc R U . . .
H20B H 0.4750 -0.0714 0.3349 0.098 Uiso 1 1 calc R U . . .
H20C H 0.5567 0.0619 0.3120 0.098 Uiso 1 1 calc R U . . .
N1 N 0.34958(15) 0.41997(17) 1.15608(16) 0.0453(4) Uani 1 1 d . . . . .
O1 O 0.39101(15) 0.25132(15) 0.91377(14) 0.0571(4) Uani 1 1 d . . . . .
O2 O 0.3909(2) 0.2669(2) 0.33121(17) 0.0908(6) Uani 1 1 d . . . . .
O3 O 0.40424(15) 0.12996(14) 0.44820(13) 0.0547(4) 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
C2 C1 N1 127.84(15) . . ?
C2 C1 C6 122.52(16) . . ?
N1 C1 C6 109.64(14) . . ?
C1 C2 C3 117.64(17) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 121.03(17) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.96(17) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 119.24(17) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 118.47(15) . . ?
C5 C6 C7 134.35(15) . . ?
C1 C6 C7 107.15(13) . . ?
C9 C7 C6 129.49(14) . . ?
C9 C7 C8 125.02(14) . . ?
C6 C7 C8 105.32(12) . . ?
O1 C8 N1 124.21(14) . . ?
O1 C8 C7 129.55(15) . . ?
N1 C8 C7 106.23(13) . . ?
C7 C9 C17 121.96(14) . . ?
C7 C9 C10 120.32(14) . . ?
C17 C9 C10 117.69(13) . . ?
C15 C10 C11 118.63(15) . . ?
C15 C10 C9 120.85(15) . . ?
C11 C10 C9 120.52(14) . . ?
C12 C11 C10 120.33(17) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 121.45(18) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 117.78(16) . . ?
C14 C13 C16 121.1(2) . . ?
C12 C13 C16 121.2(2) . . ?
C13 C14 C15 121.48(18) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C10 C15 C14 120.32(18) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C9 124.01(15) . . ?
C18 C17 H17 118.0 . . ?
C9 C17 H17 118.0 . . ?
C17 C18 C19 125.09(15) . . ?
C17 C18 H18 117.5 . . ?
C19 C18 H18 117.5 . . ?
O2 C19 O3 122.79(17) . . ?
O2 C19 C18 123.22(16) . . ?
O3 C19 C18 113.97(14) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C8 N1 C1 111.46(13) . . ?
C19 O3 C20 117.09(14) . . ?
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 1.376(2) . ?
C1 N1 1.400(2) . ?
C1 C6 1.401(2) . ?
C2 C3 1.380(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.466(2) . ?
C7 C9 1.363(2) . ?
C7 C8 1.516(2) . ?
C8 O1 1.218(2) . ?
C8 N1 1.365(2) . ?
C9 C17 1.454(2) . ?
C9 C10 1.493(2) . ?
C10 C15 1.381(2) . ?
C10 C11 1.387(2) . ?
C11 C12 1.384(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(3) . ?
C13 C16 1.512(2) . ?
C14 C15 1.387(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.326(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.465(2) . ?
C18 H18 0.9300 . ?
C19 O2 1.204(2) . ?
C19 O3 1.315(2) . ?
C20 O3 1.446(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
N1 C1 C2 C3 -177.61(17) . . . . ?
C6 C1 C2 C3 2.3(3) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C2 C3 C4 C5 -2.6(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 2.6(3) . . . . ?
C4 C5 C6 C7 -179.91(18) . . . . ?
C2 C1 C6 C5 -4.1(3) . . . . ?
N1 C1 C6 C5 175.76(15) . . . . ?
C2 C1 C6 C7 177.72(16) . . . . ?
N1 C1 C6 C7 -2.37(19) . . . . ?
C5 C6 C7 C9 10.9(3) . . . . ?
C1 C6 C7 C9 -171.42(16) . . . . ?
C5 C6 C7 C8 -173.63(19) . . . . ?
C1 C6 C7 C8 4.06(17) . . . . ?
C9 C7 C8 O1 -7.6(3) . . . . ?
C6 C7 C8 O1 176.69(18) . . . . ?
C9 C7 C8 N1 171.37(15) . . . . ?
C6 C7 C8 N1 -4.38(17) . . . . ?
C6 C7 C9 C17 179.99(15) . . . . ?
C8 C7 C9 C17 5.3(3) . . . . ?
C6 C7 C9 C10 2.0(3) . . . . ?
C8 C7 C9 C10 -172.63(14) . . . . ?
C7 C9 C10 C15 -105.91(19) . . . . ?
C17 C9 C10 C15 76.1(2) . . . . ?
C7 C9 C10 C11 74.4(2) . . . . ?
C17 C9 C10 C11 -103.67(18) . . . . ?
C15 C10 C11 C12 1.1(2) . . . . ?
C9 C10 C11 C12 -179.15(15) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C14 -0.6(3) . . . . ?
C11 C12 C13 C16 179.10(17) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C16 C13 C14 C15 -179.42(18) . . . . ?
C11 C10 C15 C14 -1.4(3) . . . . ?
C9 C10 C15 C14 178.84(16) . . . . ?
C13 C14 C15 C10 0.7(3) . . . . ?
C7 C9 C17 C18 -174.62(17) . . . . ?
C10 C9 C17 C18 3.4(2) . . . . ?
C9 C17 C18 C19 176.37(17) . . . . ?
C17 C18 C19 O2 -170.7(2) . . . . ?
C17 C18 C19 O3 7.6(3) . . . . ?
O1 C8 N1 C1 -177.88(16) . . . . ?
C7 C8 N1 C1 3.11(18) . . . . ?
C2 C1 N1 C8 179.36(17) . . . . ?
C6 C1 N1 C8 -0.5(2) . . . . ?
O2 C19 O3 C20 1.5(3) . . . . ?
C18 C19 O3 C20 -176.87(17) . . . . ?
