#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/54/4025402.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_4025402
loop_
_publ_author_name
'Morteza Bararjanian'
'Saeed Balalaie'
'Frank Rominger'
'Barahman Movassagh'
'Hamid Reza Bijanzadeh'
_publ_contact_author_address
;      Department of Chemistry, Faculty of Science
       K. N. Toosi University of Technology
       P. O. Box: 15875-4416 
       Tehran
       Iran
;
_publ_contact_author_email       balalaie@yahoo.com
_publ_contact_author_fax         '+98 21 22853650'
_publ_contact_author_name        'Balalaie, Saeed'
_publ_contact_author_phone       '+98 21 22850266'
_publ_section_title
;
 Six-Component Reactions for the Stereoselective Synthesis of
 3-Arylidene-2-oxindoles via Sequential One-Pot Ugi/Heck
 Carbocyclization/Sonogashira/Nucleophilic Addition
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2806
_journal_page_last               2812
_journal_paper_doi               10.1021/jo902713x
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C35 H30 N2 O2'
_chemical_formula_weight         510.61
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                111.777(8)
_cell_angle_beta                 111.332(7)
_cell_angle_gamma                92.411(9)
_cell_formula_units_Z            2
_cell_length_a                   10.483(4)
_cell_length_b                   12.555(5)
_cell_length_c                   12.698(5)
_cell_measurement_reflns_used    1948
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      22.40
_cell_measurement_theta_min      2.48
_cell_volume                     1415.0(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0748
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12768
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9941
_exptl_absorpt_correction_T_min  0.9673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;

Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.

;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.190
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.190
_refine_ls_R_factor_all          0.1385
_refine_ls_R_factor_gt           0.0908
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0442P)²+0.5453P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1671
_reflns_number_gt                3846
_reflns_number_total             5772
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902713x_si_001.cif
_cod_data_source_block           sba45
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1415.1(9)
_cod_database_code               4025402
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7748(2) 0.31358(19) 0.4408(2) 0.0299(5) Uani 1 1 d . . .
C2 C 0.7753(3) 0.3108(2) 0.3321(3) 0.0303(6) Uani 1 1 d . . .
O2 O 0.8616(2) 0.37563(17) 0.32715(17) 0.0362(5) Uani 1 1 d . . .
C3 C 0.6484(3) 0.2229(2) 0.2280(3) 0.0290(6) Uani 1 1 d . . .
C4 C 0.6053(3) 0.1991(2) 0.1046(3) 0.0320(7) Uani 1 1 d . . .
C5 C 0.4644(3) 0.1387(2) 0.0204(3) 0.0355(7) Uani 1 1 d . . .
C6 C 0.3473(3) 0.0946(3) -0.0555(3) 0.0392(7) Uani 1 1 d . . .
C7 C 0.8774(3) 0.4003(2) 0.5616(2) 0.0292(6) Uani 1 1 d . . .
H7 H 0.924(3) 0.446(2) 0.539(2) 0.016(6) Uiso 1 1 d . . .
C8 C 0.9821(3) 0.3405(3) 0.6278(3) 0.0336(7) Uani 1 1 d . . .
O8 O 0.9451(2) 0.24854(19) 0.6302(2) 0.0531(6) Uani 1 1 d . . .
N9 N 1.1151(3) 0.3984(2) 0.6802(2) 0.0370(6) Uani 1 1 d . . .
H9 H 1.131(3) 0.465(2) 0.676(2) 0.022(7) Uiso 1 1 d . . .
C10 C 1.2386(3) 0.3643(3) 0.7530(3) 0.0415(8) Uani 1 1 d . . .
C11 C 0.6578(3) 0.2338(2) 0.4175(3) 0.0321(7) Uani 1 1 d . . .
C12 C 0.5783(3) 0.1782(2) 0.2887(3) 0.0314(7) Uani 1 1 d . . .
C13 C 0.4618(3) 0.0898(3) 0.2433(3) 0.0406(8) Uani 1 1 d . . .
H13 H 0.4079 0.0488 0.1564 0.049 Uiso 1 1 calc R . .
C14 C 0.4262(3) 0.0628(3) 0.3261(3) 0.0462(8) Uani 1 1 d . . .
H14 H 0.3473 0.0026 0.2958 0.055 Uiso 1 1 calc R . .
C15 C 0.5037(3) 0.1221(3) 0.4525(3) 0.0482(9) Uani 1 1 d . . .
H15 H 0.4749 0.1043 0.5080 0.058 Uiso 1 1 calc R . .
C16 C 0.6234(3) 0.2077(3) 0.5004(3) 0.0413(8) Uani 1 1 d . . .
H16 H 0.6788 0.2463 0.5873 0.050 Uiso 1 1 calc R . .
C17 C 1.2238(4) 0.3621(4) 0.8663(3) 0.0687(12) Uani 1 1 d . . .
H17A H 1.2086 0.4381 0.9142 0.103 Uiso 1 1 calc R . .
H17B H 1.3094 0.3461 0.9181 0.103 Uiso 1 1 calc R . .
H17C H 1.1440 0.3005 0.8400 0.103 Uiso 1 1 calc R . .
C18 C 1.3649(3) 0.4574(3) 0.7923(4) 0.0672(12) Uani 1 1 d . . .
H18A H 1.3729 0.4587 0.7182 0.101 Uiso 1 1 calc R . .
H18B H 1.4499 0.4391 0.8419 0.101 Uiso 1 1 calc R . .
H18C H 1.3531 0.5343 0.8420 0.101 Uiso 1 1 calc R . .
C19 C 1.2541(4) 0.2461(3) 0.6716(3) 0.0575(10) Uani 1 1 d . . .
H19A H 1.1730 0.1862 0.6464 0.086 Uiso 1 1 calc R . .
H19B H 1.3396 0.2261 0.7182 0.086 Uiso 1 1 calc R . .
H19C H 1.2597 0.2496 0.5975 0.086 Uiso 1 1 calc R . .
C21 C 0.8072(3) 0.4769(2) 0.6376(3) 0.0342(7) Uani 1 1 d . . .
C22 C 0.7277(4) 0.5469(4) 0.5923(4) 0.0731(13) Uani 1 1 d . . .
H22 H 0.7183 0.5456 0.5145 0.088 Uiso 1 1 calc R . .
C23 C 0.6616(5) 0.6187(4) 0.6567(4) 0.0912(16) Uani 1 1 d . . .
H23 H 0.6071 0.6660 0.6230 0.109 Uiso 1 1 calc R . .
C24 C 0.6732(4) 0.6226(4) 0.7676(4) 0.0718(12) Uani 1 1 d . . .
H24 H 0.6263 0.6714 0.8117 0.086 Uiso 1 1 calc R . .
C25 C 0.7531(5) 0.5559(4) 0.8145(4) 0.0740(12) Uani 1 1 d . . .
H25 H 0.7628 0.5585 0.8929 0.089 Uiso 1 1 calc R . .
C26 C 0.8213(4) 0.4833(3) 0.7501(3) 0.0587(10) Uani 1 1 d . . .
H26 H 0.8781 0.4379 0.7853 0.070 Uiso 1 1 calc R . .
C31 C 0.6910(3) 0.2292(2) 0.0455(3) 0.0342(7) Uani 1 1 d . . .
C32 C 0.8327(3) 0.2261(3) 0.0851(3) 0.0446(8) Uani 1 1 d . . .
H32 H 0.8782 0.2087 0.1548 0.053 Uiso 1 1 calc R . .
C33 C 0.9067(4) 0.2484(3) 0.0228(4) 0.0637(11) Uani 1 1 d . . .
H33 H 1.0034 0.2462 0.0504 0.076 Uiso 1 1 calc R . .
C34 C 0.8442(5) 0.2738(4) -0.0782(4) 0.0704(12) Uani 1 1 d . . .
H34 H 0.8969 0.2889 -0.1200 0.085 Uiso 1 1 calc R . .
C35 C 0.7044(4) 0.2771(3) -0.1180(3) 0.0614(10) Uani 1 1 d . . .
H35 H 0.6598 0.2953 -0.1873 0.074 Uiso 1 1 calc R . .
C36 C 0.6297(4) 0.2542(3) -0.0574(3) 0.0465(8) Uani 1 1 d . . .
H36 H 0.5327 0.2553 -0.0867 0.056 Uiso 1 1 calc R . .
C41 C 0.2061(3) 0.0409(3) -0.1437(3) 0.0390(7) Uani 1 1 d . . .
C42 C 0.1004(3) 0.0393(3) -0.1031(3) 0.0562(10) Uani 1 1 d . . .
H42 H 0.1210 0.0754 -0.0169 0.067 Uiso 1 1 calc R . .
C43 C -0.0353(4) -0.0150(4) -0.1885(4) 0.0728(12) Uani 1 1 d . . .
H43 H -0.1080 -0.0158 -0.1608 0.087 Uiso 1 1 calc R . .
C44 C -0.0655(4) -0.0676(4) -0.3129(4) 0.0768(13) Uani 1 1 d . . .
H44 H -0.1587 -0.1057 -0.3710 0.092 Uiso 1 1 calc R . .
C45 C 0.0392(4) -0.0653(3) -0.3541(3) 0.0654(11) Uani 1 1 d . . .
H45 H 0.0178 -0.1009 -0.4405 0.078 Uiso 1 1 calc R . .
C46 C 0.1751(3) -0.0113(3) -0.2698(3) 0.0450(8) Uani 1 1 d . . .
H46 H 0.2472 -0.0100 -0.2980 0.054 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
C2 N1 C11 111.0(2) . . ?
C2 N1 C7 120.9(2) . . ?
C11 N1 C7 127.7(2) . . ?
O2 C2 N1 123.8(2) . . ?
O2 C2 C3 128.8(3) . . ?
N1 C2 C3 107.2(2) . . ?
C4 C3 C12 128.9(2) . . ?
C4 C3 C2 125.8(3) . . ?
C12 C3 C2 105.1(2) . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 C31 126.4(2) . . ?
C5 C4 C31 114.3(2) . . ?
C6 C5 C4 174.1(3) . . ?
C5 C6 C41 178.3(3) . . ?
N1 C7 C21 111.7(2) . . ?
N1 C7 C8 110.4(2) . . ?
C21 C7 C8 115.0(2) . . ?
N1 C7 H7 102.3(15) . . ?
C21 C7 H7 108.6(15) . . ?
C8 C7 H7 108.0(15) . . ?
O8 C8 N9 124.6(3) . . ?
O8 C8 C7 121.9(3) . . ?
N9 C8 C7 113.5(3) . . ?
C8 N9 C10 126.2(3) . . ?
C8 N9 H9 117.8(17) . . ?
C10 N9 H9 115.9(17) . . ?
N9 C10 C17 109.7(3) . . ?
N9 C10 C19 109.5(2) . . ?
C17 C10 C19 111.5(3) . . ?
N9 C10 C18 106.3(3) . . ?
C17 C10 C18 110.2(3) . . ?
C19 C10 C18 109.4(3) . . ?
C16 C11 C12 122.7(3) . . ?
C16 C11 N1 128.8(3) . . ?
C12 C11 N1 108.5(2) . . ?
C13 C12 C11 118.5(3) . . ?
C13 C12 C3 133.1(3) . . ?
C11 C12 C3 108.2(2) . . ?
C14 C13 C12 119.2(3) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 120.8(3) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C16 121.3(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C11 C16 C15 117.4(3) . . ?
C11 C16 H16 121.3 . . ?
C15 C16 H16 121.3 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C26 C21 C22 117.7(3) . . ?
C26 C21 C7 123.7(3) . . ?
C22 C21 C7 118.6(3) . . ?
C23 C22 C21 121.6(4) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C24 C23 C22 120.5(4) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 118.7(4) . . ?
C23 C24 H24 120.7 . . ?
C25 C24 H24 120.7 . . ?
C24 C25 C26 121.1(4) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C21 C26 C25 120.4(4) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C36 C31 C32 117.7(3) . . ?
C36 C31 C4 120.5(3) . . ?
C32 C31 C4 121.6(3) . . ?
C33 C32 C31 119.7(3) . . ?
C33 C32 H32 120.2 . . ?
C31 C32 H32 120.2 . . ?
C34 C33 C32 121.6(4) . . ?
C34 C33 H33 119.2 . . ?
C32 C33 H33 119.2 . . ?
C35 C34 C33 119.2(4) . . ?
C35 C34 H34 120.4 . . ?
C33 C34 H34 120.4 . . ?
C36 C35 C34 119.7(4) . . ?
C36 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
C35 C36 C31 122.1(3) . . ?
C35 C36 H36 118.9 . . ?
C31 C36 H36 118.9 . . ?
C42 C41 C46 119.8(3) . . ?
C42 C41 C6 119.9(3) . . ?
C46 C41 C6 120.3(3) . . ?
C43 C42 C41 119.8(3) . . ?
C43 C42 H42 120.1 . . ?
C41 C42 H42 120.1 . . ?
C44 C43 C42 120.4(4) . . ?
C44 C43 H43 119.8 . . ?
C42 C43 H43 119.8 . . ?
C43 C44 C45 120.2(3) . . ?
C43 C44 H44 119.9 . . ?
C45 C44 H44 119.9 . . ?
C46 C45 C44 120.0(3) . . ?
C46 C45 H45 120.0 . . ?
C44 C45 H45 120.0 . . ?
C45 C46 C41 119.9(3) . . ?
C45 C46 H46 120.0 . . ?
C41 C46 H46 120.0 . . ?
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
N1 C2 1.369(3) . ?
N1 C11 1.417(3) . ?
N1 C7 1.469(3) . ?
C2 O2 1.226(3) . ?
C2 C3 1.500(4) . ?
C3 C4 1.368(4) . ?
C3 C12 1.465(4) . ?
C4 C5 1.434(4) . ?
C4 C31 1.479(4) . ?
C5 C6 1.195(4) . ?
C6 C41 1.432(4) . ?
C7 C21 1.512(4) . ?
C7 C8 1.530(4) . ?
C7 H7 0.92(2) . ?
C8 O8 1.216(3) . ?
C8 N9 1.341(4) . ?
N9 C10 1.478(4) . ?
N9 H9 0.87(3) . ?
C10 C17 1.512(5) . ?
C10 C19 1.518(4) . ?
C10 C18 1.525(5) . ?
C11 C16 1.368(4) . ?
C11 C12 1.403(4) . ?
C12 C13 1.398(4) . ?
C13 C14 1.378(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 C26 1.353(4) . ?
C21 C22 1.373(4) . ?
C22 C23 1.371(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.350(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.351(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.393(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C36 1.388(4) . ?
C31 C32 1.392(4) . ?
C32 C33 1.378(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.373(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.373(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.369(5) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C42 1.384(4) . ?
C41 C46 1.386(4) . ?
C42 C43 1.383(5) . ?
C42 H42 0.9500 . ?
C43 C44 1.369(5) . ?
C43 H43 0.9500 . ?
C44 C45 1.380(5) . ?
C44 H44 0.9500 . ?
C45 C46 1.380(4) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139091481
