#------------------------------------------------------------------------------
#$Date: 2025-08-18 15:30:32 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301775 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/30/1503083.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_1503083
loop_
_publ_author_name
'Ignatenko, Vasily A.'
'Deligonul, Nihal'
'Viswanathan, Rajesh'
_publ_section_title
;
 Branch-selective synthesis of oxindole and indene scaffolds: transition
 metal-controlled intramolecular aryl amidation leading to c3
 reverse-prenylated oxindoles.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              3594
_journal_page_last               3597
_journal_paper_doi               10.1021/ol1012372
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C22 H22 N2 O'
_chemical_formula_sum            'C22 H22 N2 O'
_chemical_formula_weight         330.42
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3995(11)
_cell_length_b                   12.2643(16)
_cell_length_c                   17.383(2)
_cell_measurement_reflns_used    4659
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      22.75
_cell_measurement_theta_min      2.34
_cell_volume                     1790.7(4)
_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      170(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker AXS APEX II 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  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20504
_diffrn_reflns_theta_full        27.04
_diffrn_reflns_theta_max         27.04
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        none
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9899
_exptl_absorpt_correction_T_min  0.9839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'AXScale in APEX 2 (Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.343
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2240
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.343
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0385
_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)+(0.0377P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0867
_reflns_number_gt                1872
_reflns_number_total             2240
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol1012372_si_002.cif
_cod_data_source_block           nd052510_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1503083
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
N1 N 0.71924(19) 0.53951(12) 0.85605(9) 0.0311(4) Uani 1 1 d .
N2 N 0.6937(3) 0.87417(16) 0.80992(12) 0.0539(5) Uani 1 1 d .
O1 O 0.77457(19) 0.62343(11) 0.97017(8) 0.0448(4) Uani 1 1 d .
C8 C 0.7741(2) 0.54436(14) 0.77996(11) 0.0303(4) Uani 1 1 d .
C1 C 0.8051(2) 0.60670(15) 0.90262(11) 0.0327(4) Uani 1 1 d .
C21 C 0.9454(2) 0.77894(15) 0.86478(12) 0.0370(5) Uani 1 1 d .
H21A H 0.9550 0.7973 0.9200 0.044 Uiso 1 1 calc R
H21B H 1.0405 0.8081 0.8382 0.044 Uiso 1 1 calc R
C2 C 0.9429(2) 0.65443(15) 0.85600(11) 0.0305(4) Uani 1 1 d .
C10 C 0.6204(2) 0.35940(16) 0.89622(11) 0.0312(4) Uani 1 1 d .
C7 C 0.7162(3) 0.49065(17) 0.71674(12) 0.0380(5) Uani 1 1 d .
H7 H 0.6314 0.4398 0.7212 0.046 Uiso 1 1 calc R
C3 C 0.9021(2) 0.61662(15) 0.77572(11) 0.0304(4) Uani 1 1 d .
C4 C 0.9669(3) 0.64033(17) 0.70480(11) 0.0383(5) Uani 1 1 d .
H4 H 1.0506 0.6920 0.7002 0.046 Uiso 1 1 calc R
C11 C 0.5482(3) 0.27740(18) 0.85475(13) 0.0429(5) Uani 1 1 d .
H11 H 0.4722 0.2951 0.8162 0.052 Uiso 1 1 calc R
C22 C 0.8040(3) 0.83199(16) 0.83379(12) 0.0376(5) Uani 1 1 d .
C15 C 0.7295(3) 0.33074(17) 0.95241(11) 0.0384(5) Uani 1 1 d .
H15 H 0.7805 0.3862 0.9816 0.046 Uiso 1 1 calc R
C16 C 1.1064(3) 0.60439(16) 0.88533(11) 0.0337(5) Uani 1 1 d .
C6 C 0.7850(3) 0.51283(18) 0.64649(13) 0.0432(5) Uani 1 1 d .
H6 H 0.7476 0.4764 0.6018 0.052 Uiso 1 1 calc R
C19 C 1.2399(2) 0.64727(17) 0.83605(12) 0.0389(5) Uani 1 1 d .
H19 H 1.2436 0.6220 0.7844 0.047 Uiso 1 1 calc R
C9 C 0.5818(3) 0.47713(17) 0.88144(13) 0.0397(5) Uani 1 1 d .
H9A H 0.4976 0.4816 0.8417 0.048 Uiso 1 1 calc R
H9B H 0.5393 0.5101 0.9292 0.048 Uiso 1 1 calc R
C17 C 1.1031(3) 0.47973(15) 0.87588(13) 0.0412(5) Uani 1 1 d .
H17A H 1.2045 0.4490 0.8934 0.062 Uiso 1 1 calc R
H17B H 1.0868 0.4614 0.8216 0.062 Uiso 1 1 calc R
H17C H 1.0159 0.4493 0.9066 0.062 Uiso 1 1 calc R
C14 C 0.7650(3) 0.22361(18) 0.96658(13) 0.0482(6) Uani 1 1 d .
H14 H 0.8393 0.2052 1.0057 0.058 Uiso 1 1 calc R
C20 C 1.3516(3) 0.71581(19) 0.85696(16) 0.0512(6) Uani 1 1 d .
H20A H 1.3534 0.7436 0.9080 0.061 Uiso 1 1 calc R
H20B H 1.4307 0.7377 0.8211 0.061 Uiso 1 1 calc R
C18 C 1.1351(3) 0.62936(19) 0.97028(12) 0.0447(5) Uani 1 1 d .
H18A H 1.1329 0.7084 0.9783 0.067 Uiso 1 1 calc R
H18B H 1.2393 0.6007 0.9857 0.067 Uiso 1 1 calc R
H18C H 1.0517 0.5950 1.0013 0.067 Uiso 1 1 calc R
C12 C 0.5857(3) 0.16942(18) 0.86886(14) 0.0524(6) Uani 1 1 d .
H12 H 0.5362 0.1134 0.8397 0.063 Uiso 1 1 calc R
C13 C 0.6933(3) 0.14304(18) 0.92438(14) 0.0531(6) Uani 1 1 d .
H13 H 0.7187 0.0688 0.9339 0.064 Uiso 1 1 calc R
C5 C 0.9076(3) 0.58734(19) 0.64020(12) 0.0439(5) Uani 1 1 d .
H5 H 0.9520 0.6025 0.5911 0.053 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 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
C1 N1 C8 111.17(15)
C1 N1 C9 123.97(16)
C8 N1 C9 124.73(16)
C7 C8 C3 122.43(18)
C7 C8 N1 128.30(18)
C3 C8 N1 109.26(16)
O1 C1 N1 124.25(19)
O1 C1 C2 127.24(19)
N1 C1 C2 108.51(16)
C22 C21 C2 113.37(17)
C22 C21 H21A 108.9
C2 C21 H21A 108.9
C22 C21 H21B 108.9
C2 C21 H21B 108.9
H21A C21 H21B 107.7
C3 C2 C1 101.55(15)
C3 C2 C21 113.61(16)
C1 C2 C21 109.77(16)
C3 C2 C16 111.99(16)
C1 C2 C16 109.65(14)
C21 C2 C16 109.94(16)
C11 C10 C15 118.35(19)
C11 C10 C9 121.14(19)
C15 C10 C9 120.51(18)
C8 C7 C6 117.83(19)
C8 C7 H7 121.1
C6 C7 H7 121.1
C4 C3 C8 119.04(18)
C4 C3 C2 132.21(18)
C8 C3 C2 108.75(16)
C3 C4 C5 118.84(19)
C3 C4 H4 120.6
C5 C4 H4 120.6
C10 C11 C12 120.4(2)
C10 C11 H11 119.8
C12 C11 H11 119.8
N2 C22 C21 179.5(2)
C14 C15 C10 121.0(2)
C14 C15 H15 119.5
C10 C15 H15 119.5
C19 C16 C18 111.22(18)
C19 C16 C17 107.43(17)
C18 C16 C17 107.78(17)
C19 C16 C2 109.04(15)
C18 C16 C2 111.70(17)
C17 C16 C2 109.55(17)
C7 C6 C5 120.9(2)
C7 C6 H6 119.5
C5 C6 H6 119.5
C20 C19 C16 126.8(2)
C20 C19 H19 116.6
C16 C19 H19 116.6
N1 C9 C10 112.73(17)
N1 C9 H9A 109.0
C10 C9 H9A 109.0
N1 C9 H9B 109.0
C10 C9 H9B 109.0
H9A C9 H9B 107.8
C16 C17 H17A 109.5
C16 C17 H17B 109.5
H17A C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C15 C14 C13 120.0(2)
C15 C14 H14 120.0
C13 C14 H14 120.0
C19 C20 H20A 120.0
C19 C20 H20B 120.0
H20A C20 H20B 120.0
C16 C18 H18A 109.5
C16 C18 H18B 109.5
H18A C18 H18B 109.5
C16 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C13 C12 C11 120.3(2)
C13 C12 H12 119.8
C11 C12 H12 119.8
C12 C13 C14 120.0(2)
C12 C13 H13 120.0
C14 C13 H13 120.0
C6 C5 C4 120.8(2)
C6 C5 H5 119.6
C4 C5 H5 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.362(3)
N1 C8 1.402(2)
N1 C9 1.454(2)
N2 C22 1.140(3)
O1 C1 1.219(2)
C8 C7 1.370(3)
C8 C3 1.395(3)
C1 C2 1.529(3)
C21 C22 1.457(3)
C21 C2 1.535(3)
C21 H21A 0.9900
C21 H21B 0.9900
C2 C3 1.510(3)
C2 C16 1.588(3)
C10 C11 1.378(3)
C10 C15 1.385(3)
C10 C9 1.502(3)
C7 C6 1.378(3)
C7 H7 0.9500
C3 C4 1.379(3)
C4 C5 1.390(3)
C4 H4 0.9500
C11 C12 1.383(3)
C11 H11 0.9500
C15 C14 1.370(3)
C15 H15 0.9500
C16 C19 1.506(3)
C16 C18 1.527(3)
C16 C17 1.538(3)
C6 C5 1.381(3)
C6 H6 0.9500
C19 C20 1.311(3)
C19 H19 0.9500
C9 H9A 0.9900
C9 H9B 0.9900
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C14 C13 1.370(3)
C14 H14 0.9500
C20 H20A 0.9500
C20 H20B 0.9500
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
C12 C13 1.361(4)
C12 H12 0.9500
C13 H13 0.9500
C5 H5 0.9500
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139037788
