#------------------------------------------------------------------------------
#$Date: 2024-10-05 14:34:25 +0200 (Sat 05 de Oct de 2024) $
#$Revision: 295072 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/01/7160167.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_7160167
loop_
_publ_author_name
'Chouhan, Raju'
'Gogoi, Abhijit'
'Das, Sajal Kumar'
_publ_section_title
;
 Constructing spirooxindoles from non-oxindole precursors: a one-pot
 nitro-reduction/double lactamization approach to
 spiro[indoline-3,3'-quinoline]-2,2'-diones.
;
_journal_issue                   37
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7601
_journal_page_last               7606
_journal_paper_doi               10.1039/d4ob01178c
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C16 H12 N2 O2'
_chemical_formula_sum            'C16 H12 N2 O2'
_chemical_formula_weight         264.28
_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
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2kcyfb
_audit_creation_date             2024-04-09
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-06-24 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                102.192(10)
_cell_angle_beta                 96.254(10)
_cell_angle_gamma                105.998(9)
_cell_formula_units_Z            2
_cell_length_a                   5.713(2)
_cell_length_b                   9.479(4)
_cell_length_c                   12.310(5)
_cell_measurement_reflns_used    2723
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.86
_cell_measurement_theta_min      2.31
_cell_volume                     616.4(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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  0.0956
_diffrn_reflns_av_unetI/netI     0.0753
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20817
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.860
_diffrn_reflns_theta_min         1.720
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5821
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1187 before and 0.0880 after correction.
The Ratio of minimum to maximum transmission is 0.7806.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate/ haxane'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.054(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3210
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0534
_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)+(0.0585P)²+0.1574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1432
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2172
_reflns_number_total             3210
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01178c2.cif
_cod_data_source_block           ag453_a
_cod_database_code               7160167
_shelx_shelxl_version_number     2019/3
_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_max   0.981
_shelx_estimated_absorpt_t_min   0.976
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C4(H4), C13(H13), C16(H16), C14(H14), C5(H5), C7(H7),
 C15(H15), C6(H6)
;
_olex2_date_sample_data_collection 2024-03-26
_olex2_date_sample_submission    2024-03-26
_olex2_submission_original_sample_id AG453
_olex2_submission_special_instructions 'No special instructions were received'
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
O2 O 0.6587(2) 0.34804(13) 0.47438(10) 0.0242(3) Uani 1 1 d . . . . .
O1 O 1.1170(2) 0.21625(14) 0.51866(11) 0.0265(3) Uani 1 1 d . . . . .
N2 N 0.7482(3) 0.54961(16) 0.62484(12) 0.0219(3) Uani 1 1 d . . . . .
H2 H 0.672303 0.594378 0.585938 0.026 Uiso 1 1 calc R U . . .
N1 N 0.7940(3) 0.07129(16) 0.58220(13) 0.0229(4) Uani 1 1 d . . . . .
H1 H 0.787841 -0.016753 0.543157 0.027 Uiso 1 1 calc R U . . .
C3 C 0.6975(3) 0.25109(19) 0.70939(15) 0.0193(4) Uani 1 1 d . . . . .
C2 C 0.8874(3) 0.33524(19) 0.64921(15) 0.0195(4) Uani 1 1 d . . . . .
C1 C 0.9517(3) 0.20355(19) 0.57420(15) 0.0208(4) Uani 1 1 d . . . . .
C12 C 0.7563(3) 0.41098(19) 0.57316(15) 0.0203(4) Uani 1 1 d . . . . .
C4 C 0.5777(3) 0.3008(2) 0.79394(15) 0.0218(4) Uani 1 1 d . . . . .
H4 H 0.615144 0.403718 0.827655 0.026 Uiso 1 1 calc R U . . .
C10 C 1.0435(3) 0.58404(19) 0.79167(15) 0.0210(4) Uani 1 1 d . . . . .
C11 C 0.8549(3) 0.62589(19) 0.73752(15) 0.0204(4) Uani 1 1 d . . . . .
C8 C 0.6423(3) 0.09566(19) 0.66186(15) 0.0211(4) Uani 1 1 d . . . . .
C9 C 1.1169(3) 0.45562(19) 0.72561(15) 0.0223(4) Uani 1 1 d . . . . .
H9A H 1.194789 0.410469 0.777097 0.027 Uiso 1 1 calc R U . . .
H9B H 1.235466 0.493737 0.679847 0.027 Uiso 1 1 calc R U . . .
C13 C 0.7662(3) 0.73699(19) 0.79551(16) 0.0236(4) Uani 1 1 d . . . . .
H13 H 0.639432 0.763503 0.759178 0.028 Uiso 1 1 calc R U . . .
C16 C 1.1423(3) 0.6564(2) 0.90390(16) 0.0254(4) Uani 1 1 d . . . . .
H16 H 1.267571 0.629174 0.940723 0.031 Uiso 1 1 calc R U . . .
C14 C 0.8682(4) 0.8081(2) 0.90808(16) 0.0252(4) Uani 1 1 d . . . . .
H14 H 0.809177 0.882456 0.947155 0.030 Uiso 1 1 calc R U . . .
C5 C 0.3990(3) 0.1937(2) 0.82808(16) 0.0246(4) Uani 1 1 d . . . . .
H5 H 0.318107 0.225663 0.885614 0.030 Uiso 1 1 calc R U . . .
C7 C 0.4609(3) -0.0116(2) 0.69245(16) 0.0245(4) Uani 1 1 d . . . . .
H7 H 0.420849 -0.114366 0.657671 0.029 Uiso 1 1 calc R U . . .
C15 C 1.0572(4) 0.7692(2) 0.96267(16) 0.0271(4) Uani 1 1 d . . . . .
H15 H 1.126599 0.817971 1.037810 0.033 Uiso 1 1 calc R U . . .
C6 C 0.3412(3) 0.0408(2) 0.77726(16) 0.0260(4) Uani 1 1 d . . . . .
H6 H 0.219553 -0.028448 0.800336 0.031 Uiso 1 1 calc R U . . .
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_
_citation_id
_citation_doi
_citation_year
1 10.1039/d4ob01178c 2024
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
C12 N2 H2 117.7 . . ?
C12 N2 C11 124.64(15) . . ?
C11 N2 H2 117.7 . . ?
C1 N1 H1 124.1 . . ?
C1 N1 C8 111.78(15) . . ?
C8 N1 H1 124.1 . . ?
C4 C3 C2 132.25(16) . . ?
C4 C3 C8 119.55(16) . . ?
C8 C3 C2 108.18(15) . . ?
C3 C2 C1 101.76(13) . . ?
C3 C2 C12 107.97(14) . . ?
C3 C2 C9 115.95(15) . . ?
C12 C2 C1 109.15(14) . . ?
C9 C2 C1 112.59(14) . . ?
C9 C2 C12 109.06(14) . . ?
O1 C1 N1 126.04(16) . . ?
O1 C1 C2 125.97(16) . . ?
N1 C1 C2 107.98(15) . . ?
O2 C12 N2 122.39(16) . . ?
O2 C12 C2 122.76(15) . . ?
N2 C12 C2 114.80(15) . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.81(17) . . ?
C5 C4 H4 120.6 . . ?
C11 C10 C9 117.46(16) . . ?
C16 C10 C11 118.80(17) . . ?
C16 C10 C9 123.64(16) . . ?
C10 C11 N2 119.11(16) . . ?
C13 C11 N2 120.14(16) . . ?
C13 C11 C10 120.70(17) . . ?
C3 C8 N1 109.70(15) . . ?
C7 C8 N1 127.99(16) . . ?
C7 C8 C3 122.31(17) . . ?
C2 C9 H9A 109.7 . . ?
C2 C9 H9B 109.7 . . ?
C10 C9 C2 109.89(15) . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C11 C13 H13 120.2 . . ?
C14 C13 C11 119.51(17) . . ?
C14 C13 H13 120.2 . . ?
C10 C16 H16 119.4 . . ?
C10 C16 C15 121.12(18) . . ?
C15 C16 H16 119.4 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.53(17) . . ?
C15 C14 H14 119.7 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.69(18) . . ?
C6 C5 H5 119.7 . . ?
C8 C7 H7 121.4 . . ?
C8 C7 C6 117.19(17) . . ?
C6 C7 H7 121.4 . . ?
C16 C15 H15 120.3 . . ?
C14 C15 C16 119.34(18) . . ?
C14 C15 H15 120.3 . . ?
C5 C6 C7 121.37(17) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
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
O2 C12 1.228(2) . ?
O1 C1 1.219(2) . ?
N2 H2 0.8600 . ?
N2 C12 1.349(2) . ?
N2 C11 1.403(2) . ?
N1 H1 0.8600 . ?
N1 C1 1.357(2) . ?
N1 C8 1.402(2) . ?
C3 C2 1.520(2) . ?
C3 C4 1.378(2) . ?
C3 C8 1.397(2) . ?
C2 C1 1.544(2) . ?
C2 C12 1.543(2) . ?
C2 C9 1.536(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.397(2) . ?
C10 C11 1.397(3) . ?
C10 C9 1.502(2) . ?
C10 C16 1.383(3) . ?
C11 C13 1.390(2) . ?
C8 C7 1.384(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C13 H13 0.9300 . ?
C13 C14 1.388(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.393(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.389(3) . ?
C15 H15 0.9300 . ?
C6 H6 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
N2 C11 C13 C14 177.93(16) . . . . ?
N1 C8 C7 C6 177.60(17) . . . . ?
C3 C2 C1 O1 -171.69(17) . . . . ?
C3 C2 C1 N1 7.51(17) . . . . ?
C3 C2 C12 O2 -90.75(19) . . . . ?
C3 C2 C12 N2 86.70(18) . . . . ?
C3 C2 C9 C10 -66.33(19) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C3 C8 C7 C6 -3.0(3) . . . . ?
C2 C3 C4 C5 176.43(18) . . . . ?
C2 C3 C8 N1 4.57(19) . . . . ?
C2 C3 C8 C7 -174.95(16) . . . . ?
C1 N1 C8 C3 0.5(2) . . . . ?
C1 N1 C8 C7 -179.97(18) . . . . ?
C1 C2 C12 O2 19.1(2) . . . . ?
C1 C2 C12 N2 -163.46(15) . . . . ?
C1 C2 C9 C10 177.06(14) . . . . ?
C12 N2 C11 C10 20.9(3) . . . . ?
C12 N2 C11 C13 -156.39(17) . . . . ?
C12 C2 C1 O1 74.4(2) . . . . ?
C12 C2 C1 N1 -106.43(16) . . . . ?
C12 C2 C9 C10 55.74(19) . . . . ?
C4 C3 C2 C1 174.71(19) . . . . ?
C4 C3 C2 C12 -70.5(2) . . . . ?
C4 C3 C2 C9 52.2(3) . . . . ?
C4 C3 C8 N1 -177.03(16) . . . . ?
C4 C3 C8 C7 3.5(3) . . . . ?
C4 C5 C6 C7 1.1(3) . . . . ?
C10 C11 C13 C14 0.7(3) . . . . ?
C10 C16 C15 C14 0.9(3) . . . . ?
C11 N2 C12 O2 179.51(16) . . . . ?
C11 N2 C12 C2 2.0(2) . . . . ?
C11 C10 C9 C2 -36.5(2) . . . . ?
C11 C10 C16 C15 -0.1(3) . . . . ?
C11 C13 C14 C15 0.0(3) . . . . ?
C8 N1 C1 O1 173.87(17) . . . . ?
C8 N1 C1 C2 -5.33(19) . . . . ?
C8 C3 C2 C1 -7.17(18) . . . . ?
C8 C3 C2 C12 107.65(16) . . . . ?
C8 C3 C2 C9 -129.70(16) . . . . ?
C8 C3 C4 C5 -1.5(3) . . . . ?
C8 C7 C6 C5 0.7(3) . . . . ?
C9 C2 C1 O1 -46.9(2) . . . . ?
C9 C2 C1 N1 132.31(16) . . . . ?
C9 C2 C12 O2 142.47(17) . . . . ?
C9 C2 C12 N2 -40.1(2) . . . . ?
C9 C10 C11 N2 -1.4(2) . . . . ?
C9 C10 C11 C13 175.83(16) . . . . ?
C9 C10 C16 C15 -176.39(17) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C16 C10 C11 N2 -177.92(16) . . . . ?
C16 C10 C11 C13 -0.7(3) . . . . ?
C16 C10 C9 C2 139.86(17) . . . . ?
