#------------------------------------------------------------------------------
#$Date: 2025-03-28 03:57:00 +0200 (Fri, 28 Mar 2025) $
#$Revision: 298635 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/04/7160452.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_7160452
loop_
_publ_author_name
'Mondal, Nurabul'
'Kumari, Vidya'
'Ali, Danish'
'Choudhury, Lokman H.'
_publ_section_title
;
 Synthesis of indole-linked β-cyano-enones: a pathway to
 indolyl-2-pyrrolones.
;
_journal_name_full               'Organic & biomolecular chemistry'
_journal_paper_doi               10.1039/d5ob00328h
_journal_year                    2025
_chemical_formula_moiety         'C25 H16 N2 O2'
_chemical_formula_sum            'C25 H16 N2 O2'
_chemical_formula_weight         376.40
_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_creation_date             2024-05-10
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-10 deposited with the CCDC.	2025-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                101.017(8)
_cell_angle_beta                 101.391(7)
_cell_angle_gamma                93.642(7)
_cell_formula_units_Z            2
_cell_length_a                   9.2194(12)
_cell_length_b                   10.0506(14)
_cell_length_c                   10.4838(14)
_cell_measurement_reflns_used    3531
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.77
_cell_measurement_theta_min      2.27
_cell_volume                     929.6(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_av_unetI/netI     0.0826
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12101
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.001
_diffrn_reflns_theta_max         25.001
_diffrn_reflns_theta_min         2.266
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1618 before and 0.0845 after correction.
The Ratio of minimum to maximum transmission is 0.7687.
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    1.345
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.089
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.242
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3197
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.242
_refine_ls_R_factor_all          0.1669
_refine_ls_R_factor_gt           0.1078
_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)+2.0385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1812
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2020
_reflns_number_total             3197
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ob00328h2.cif
_cod_data_source_block           blank_0m
_cod_database_code               7160452
_shelx_shelxl_version_number     2019/1
_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_max   0.996
_shelx_estimated_absorpt_t_min   0.992
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C2(H2A), C16(H16), C25(H25), C3(H3), C21(H21), C12(H12),
 C4(H4), C15(H15), C22(H22), C24(H24), C23(H23), C14(H14), C5(H5), C13(H13)
;
_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 0.2656(4) 0.7362(4) 0.0420(3) 0.0447(10) Uani 1 1 d . . . . .
O1 O 0.0969(4) 0.5335(4) 0.1399(4) 0.0525(11) Uani 1 1 d . . . . .
N2 N 0.7817(5) 0.5821(5) 0.1198(4) 0.0455(12) Uani 1 1 d . . . . .
H2 H 0.857679 0.538985 0.110103 0.055 Uiso 1 1 calc R U . . .
C10 C 0.3147(5) 0.7205(5) 0.1531(5) 0.0346(12) Uani 1 1 d . . . . .
C9 C 0.4075(5) 0.6031(5) 0.1734(5) 0.0328(12) Uani 1 1 d . . . . .
C8 C 0.5564(5) 0.6252(5) 0.1541(5) 0.0352(12) Uani 1 1 d . . . . .
C1 C 0.6307(5) 0.7484(5) 0.1325(5) 0.0362(12) Uani 1 1 d . . . . .
C11 C 0.3012(5) 0.8194(5) 0.2734(5) 0.0383(13) Uani 1 1 d . . . . .
C20 C 0.1290(6) 0.4062(5) 0.3072(5) 0.0373(13) Uani 1 1 d . . . . .
C17 C 0.3444(5) 0.4952(5) 0.2122(5) 0.0363(13) Uani 1 1 d . . . . .
C19 C 0.1843(5) 0.4812(5) 0.2149(5) 0.0410(13) Uani 1 1 d . . . . .
C7 C 0.6569(6) 0.5288(6) 0.1442(5) 0.0434(14) Uani 1 1 d . . . . .
H7 H 0.639502 0.439283 0.153246 0.052 Uiso 1 1 calc R U . . .
C2 C 0.5966(6) 0.8818(5) 0.1292(5) 0.0466(14) Uani 1 1 d . . . . .
H2A H 0.505003 0.907948 0.142877 0.056 Uiso 1 1 calc R U . . .
C6 C 0.7714(6) 0.7166(6) 0.1124(5) 0.0414(14) Uani 1 1 d . . . . .
C16 C 0.3576(6) 0.8023(5) 0.4020(5) 0.0439(14) Uani 1 1 d . . . . .
H16 H 0.404518 0.725190 0.414985 0.053 Uiso 1 1 calc R U . . .
C25 C -0.0115(6) 0.3361(5) 0.2688(6) 0.0476(15) Uani 1 1 d . . . . .
H25 H -0.065021 0.327201 0.182011 0.057 Uiso 1 1 calc R U . . .
C3 C 0.6994(6) 0.9731(6) 0.1055(6) 0.0551(16) Uani 1 1 d . . . . .
H3 H 0.675889 1.061117 0.101825 0.066 Uiso 1 1 calc R U . . .
C18 C 0.4293(6) 0.3897(6) 0.2491(6) 0.0531(16) Uani 1 1 d . . . . .
C21 C 0.2079(6) 0.4171(6) 0.4352(5) 0.0496(15) Uani 1 1 d . . . . .
H21 H 0.303501 0.462299 0.461985 0.059 Uiso 1 1 calc R U . . .
C12 C 0.2356(6) 0.9370(6) 0.2576(6) 0.0532(16) Uani 1 1 d . . . . .
H12 H 0.200106 0.951563 0.172556 0.064 Uiso 1 1 calc R U . . .
C4 C 0.8384(7) 0.9376(7) 0.0868(6) 0.0616(18) Uani 1 1 d . . . . .
H4 H 0.906739 1.002811 0.073255 0.074 Uiso 1 1 calc R U . . .
C15 C 0.3441(6) 0.8994(6) 0.5101(6) 0.0527(16) Uani 1 1 d . . . . .
H15 H 0.382154 0.887819 0.595793 0.063 Uiso 1 1 calc R U . . .
N1 N 0.4956(6) 0.3045(6) 0.2776(7) 0.092(2) Uani 1 1 d . . . . .
C22 C 0.1444(7) 0.3605(6) 0.5237(6) 0.0581(17) Uani 1 1 d . . . . .
H22 H 0.197176 0.369046 0.610630 0.070 Uiso 1 1 calc R U . . .
C24 C -0.0725(7) 0.2795(6) 0.3576(6) 0.0579(17) Uani 1 1 d . . . . .
H24 H -0.167110 0.232218 0.330765 0.069 Uiso 1 1 calc R U . . .
C23 C 0.0049(7) 0.2920(6) 0.4852(7) 0.0624(18) Uani 1 1 d . . . . .
H23 H -0.037030 0.254222 0.545625 0.075 Uiso 1 1 calc R U . . .
C14 C 0.2753(7) 1.0120(6) 0.4917(6) 0.0629(18) Uani 1 1 d . . . . .
H14 H 0.263985 1.076042 0.564876 0.075 Uiso 1 1 calc R U . . .
C5 C 0.8758(6) 0.8088(7) 0.0881(6) 0.0586(17) Uani 1 1 d . . . . .
H5 H 0.967361 0.783686 0.073202 0.070 Uiso 1 1 calc R U . . .
C13 C 0.2226(7) 1.0316(6) 0.3656(7) 0.0675(19) Uani 1 1 d . . . . .
H13 H 0.177619 1.109900 0.353705 0.081 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_
_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
C7 N2 H2 125.0 . . ?
C7 N2 C6 110.1(4) . . ?
C6 N2 H2 125.0 . . ?
O2 C10 C9 119.9(4) . . ?
O2 C10 C11 122.5(5) . . ?
C11 C10 C9 117.4(4) . . ?
C8 C9 C10 113.8(4) . . ?
C17 C9 C10 118.0(4) . . ?
C17 C9 C8 128.2(4) . . ?
C9 C8 C1 128.2(4) . . ?
C7 C8 C9 126.4(5) . . ?
C7 C8 C1 105.3(4) . . ?
C2 C1 C8 136.4(5) . . ?
C6 C1 C8 106.4(4) . . ?
C6 C1 C2 117.2(5) . . ?
C16 C11 C10 122.9(5) . . ?
C12 C11 C10 118.6(5) . . ?
C12 C11 C16 118.4(5) . . ?
C25 C20 C19 119.2(5) . . ?
C21 C20 C19 121.2(5) . . ?
C21 C20 C25 119.3(5) . . ?
C9 C17 C19 121.4(4) . . ?
C9 C17 C18 121.4(5) . . ?
C18 C17 C19 117.2(5) . . ?
O1 C19 C20 119.8(5) . . ?
O1 C19 C17 119.3(5) . . ?
C20 C19 C17 120.9(5) . . ?
N2 C7 C8 110.5(5) . . ?
N2 C7 H7 124.7 . . ?
C8 C7 H7 124.7 . . ?
C1 C2 H2A 120.3 . . ?
C3 C2 C1 119.4(5) . . ?
C3 C2 H2A 120.3 . . ?
N2 C6 C1 107.6(5) . . ?
N2 C6 C5 128.7(5) . . ?
C5 C6 C1 123.7(5) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 C11 120.1(5) . . ?
C15 C16 H16 119.9 . . ?
C20 C25 H25 119.8 . . ?
C24 C25 C20 120.4(6) . . ?
C24 C25 H25 119.8 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.6(6) . . ?
C4 C3 H3 119.2 . . ?
N1 C18 C17 179.2(8) . . ?
C20 C21 H21 120.2 . . ?
C20 C21 C22 119.6(6) . . ?
C22 C21 H21 120.2 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(6) . . ?
C13 C12 H12 119.7 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.0(6) . . ?
C5 C4 H4 119.5 . . ?
C16 C15 H15 119.9 . . ?
C14 C15 C16 120.2(6) . . ?
C14 C15 H15 119.9 . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.8(6) . . ?
C23 C22 H22 119.6 . . ?
C25 C24 H24 119.8 . . ?
C23 C24 C25 120.3(6) . . ?
C23 C24 H24 119.8 . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.6(6) . . ?
C24 C23 H23 120.2 . . ?
C15 C14 H14 119.9 . . ?
C15 C14 C13 120.2(6) . . ?
C13 C14 H14 119.9 . . ?
C6 C5 H5 121.4 . . ?
C4 C5 C6 117.2(5) . . ?
C4 C5 H5 121.4 . . ?
C12 C13 C14 120.4(6) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
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 C10 1.207(5) . ?
O1 C19 1.227(6) . ?
N2 H2 0.8600 . ?
N2 C7 1.328(6) . ?
N2 C6 1.377(6) . ?
C10 C9 1.524(6) . ?
C10 C11 1.481(7) . ?
C9 C8 1.436(6) . ?
C9 C17 1.365(7) . ?
C8 C1 1.454(7) . ?
C8 C7 1.387(6) . ?
C1 C2 1.402(7) . ?
C1 C6 1.402(6) . ?
C11 C16 1.393(7) . ?
C11 C12 1.384(7) . ?
C20 C19 1.480(7) . ?
C20 C25 1.381(7) . ?
C20 C21 1.375(7) . ?
C17 C19 1.480(7) . ?
C17 C18 1.424(7) . ?
C7 H7 0.9300 . ?
C2 H2A 0.9300 . ?
C2 C3 1.368(7) . ?
C6 C5 1.386(7) . ?
C16 H16 0.9300 . ?
C16 C15 1.379(7) . ?
C25 H25 0.9300 . ?
C25 C24 1.369(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(8) . ?
C18 N1 1.135(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.378(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.363(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.363(8) . ?
C15 H15 0.9300 . ?
C15 C14 1.359(8) . ?
C22 H22 0.9300 . ?
C22 C23 1.366(8) . ?
C24 H24 0.9300 . ?
C24 C23 1.365(8) . ?
C23 H23 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.371(8) . ?
C5 H5 0.9300 . ?
C13 H13 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
O2 C10 C9 C8 75.6(6) . . . . ?
O2 C10 C9 C17 -107.2(6) . . . . ?
O2 C10 C11 C16 -179.9(5) . . . . ?
O2 C10 C11 C12 -2.9(8) . . . . ?
N2 C6 C5 C4 -179.5(6) . . . . ?
C10 C9 C8 C1 7.1(7) . . . . ?
C10 C9 C8 C7 -168.6(5) . . . . ?
C10 C9 C17 C19 9.2(7) . . . . ?
C10 C9 C17 C18 -172.1(5) . . . . ?
C10 C11 C16 C15 178.7(5) . . . . ?
C10 C11 C12 C13 -179.1(5) . . . . ?
C9 C10 C11 C16 -5.9(7) . . . . ?
C9 C10 C11 C12 171.1(5) . . . . ?
C9 C8 C1 C2 3.9(10) . . . . ?
C9 C8 C1 C6 -177.0(5) . . . . ?
C9 C8 C7 N2 176.8(5) . . . . ?
C9 C17 C19 O1 26.7(8) . . . . ?
C9 C17 C19 C20 -152.8(5) . . . . ?
C8 C9 C17 C19 -174.0(5) . . . . ?
C8 C9 C17 C18 4.7(8) . . . . ?
C8 C1 C2 C3 179.7(6) . . . . ?
C8 C1 C6 N2 0.6(6) . . . . ?
C8 C1 C6 C5 179.8(5) . . . . ?
C1 C8 C7 N2 0.3(6) . . . . ?
C1 C2 C3 C4 -1.1(9) . . . . ?
C1 C6 C5 C4 1.5(9) . . . . ?
C11 C10 C9 C8 -98.6(5) . . . . ?
C11 C10 C9 C17 78.7(6) . . . . ?
C11 C16 C15 C14 0.2(8) . . . . ?
C11 C12 C13 C14 0.5(10) . . . . ?
C20 C25 C24 C23 0.1(9) . . . . ?
C20 C21 C22 C23 1.0(9) . . . . ?
C17 C9 C8 C1 -169.8(5) . . . . ?
C17 C9 C8 C7 14.5(8) . . . . ?
C19 C20 C25 C24 -172.2(5) . . . . ?
C19 C20 C21 C22 171.5(5) . . . . ?
C7 N2 C6 C1 -0.5(6) . . . . ?
C7 N2 C6 C5 -179.6(5) . . . . ?
C7 C8 C1 C2 -179.7(6) . . . . ?
C7 C8 C1 C6 -0.6(5) . . . . ?
C2 C1 C6 N2 179.9(5) . . . . ?
C2 C1 C6 C5 -0.9(8) . . . . ?
C2 C3 C4 C5 1.7(10) . . . . ?
C6 N2 C7 C8 0.1(6) . . . . ?
C6 C1 C2 C3 0.7(8) . . . . ?
C16 C11 C12 C13 -2.0(9) . . . . ?
C16 C15 C14 C13 -1.8(9) . . . . ?
C25 C20 C19 O1 32.9(7) . . . . ?
C25 C20 C19 C17 -147.6(5) . . . . ?
C25 C20 C21 C22 -1.4(8) . . . . ?
C25 C24 C23 C22 -0.6(9) . . . . ?
C3 C4 C5 C6 -1.8(9) . . . . ?
C18 C17 C19 O1 -152.0(5) . . . . ?
C18 C17 C19 C20 28.5(7) . . . . ?
C21 C20 C19 O1 -140.1(5) . . . . ?
C21 C20 C19 C17 39.5(7) . . . . ?
C21 C20 C25 C24 0.9(8) . . . . ?
C21 C22 C23 C24 0.0(9) . . . . ?
C12 C11 C16 C15 1.7(8) . . . . ?
C15 C14 C13 C12 1.5(10) . . . . ?
