#------------------------------------------------------------------------------
#$Date: 2022-01-29 00:50:46 +0200 (Sat, 29 Jan 2022) $
#$Revision: 272323 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/96/7129638.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_7129638
loop_
_publ_author_name
'Mondal, Biplab'
'Jagadeesh, Chenna'
'Das, Dinabandhu'
'Saha, Jaideep'
_publ_section_title
;
 An acid-promoted pseudocine substitution manifold of
 γ-aminocyclopentenone enables divergent access to polycyclic indole
 derivatives
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06883K
_journal_year                    2022
_chemical_formula_sum            'C29 H24 N2 O2'
_chemical_formula_weight         432.50
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-11-02 deposited with the CCDC.	2022-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                97.315(5)
_cell_angle_beta                 97.743(6)
_cell_angle_gamma                111.251(5)
_cell_formula_units_Z            2
_cell_length_a                   10.0315(17)
_cell_length_b                   10.8177(17)
_cell_length_c                   13.014(2)
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.02
_cell_measurement_theta_min      2.36
_cell_volume                     1280.3(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'X-Seed (Barbour 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018 (Sheldrick, 2015)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-III Photon 100 detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            57585
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.384
_diffrn_reflns_theta_min         2.221
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.060
_exptl_transmission_factor_max   0.7457
_exptl_transmission_factor_min   0.7182
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.030(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         6377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0661
_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)+(0.1359P)²+0.3136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2069
_refine_ls_wR_factor_ref         0.2241
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4877
_reflns_number_total             6377
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06883k2.cif
_cod_data_source_block           BM833
_cod_database_code               7129638
_shelx_shelxl_version_number     2018/3
_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_min   0.975
_shelx_estimated_absorpt_t_max   0.996
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
O1 O 0.2698(2) 0.20973(19) 0.73596(14) 0.0792(5) Uani 1 1 d . . . . .
N1 N 0.25504(16) 0.79030(15) 0.58157(12) 0.0432(4) Uani 1 1 d . . . . .
C1 C 0.2131(2) 0.28386(19) 0.70639(16) 0.0516(5) Uani 1 1 d . . . . .
O2 O -0.02911(18) 0.5443(2) 0.88164(13) 0.0735(5) Uani 1 1 d . . . . .
N2 N 0.1988(2) 0.5857(2) 0.97409(14) 0.0601(5) Uani 1 1 d . . . . .
C2 C 0.24475(19) 0.35592(17) 0.61251(15) 0.0427(4) Uani 1 1 d . . . . .
H2 H 0.344832 0.423748 0.631439 0.051 Uiso 1 1 calc R U . . .
C3 C 0.23347(18) 0.25885(17) 0.51429(15) 0.0418(4) Uani 1 1 d . . . . .
C4 C 0.0993(2) 0.1651(2) 0.45904(19) 0.0567(5) Uani 1 1 d . . . . .
H4 H 0.014960 0.159571 0.483855 0.068 Uiso 1 1 calc R U . . .
C5 C 0.0897(3) 0.0792(3) 0.3670(2) 0.0709(7) Uani 1 1 d . . . . .
H5 H -0.001286 0.018583 0.329569 0.085 Uiso 1 1 calc R U . . .
C6 C 0.2128(3) 0.0829(3) 0.3306(2) 0.0667(6) Uani 1 1 d . . . . .
H6 H 0.205781 0.025159 0.268972 0.080 Uiso 1 1 calc R U . . .
C7 C 0.3461(3) 0.1725(2) 0.38599(19) 0.0615(6) Uani 1 1 d . . . . .
H7 H 0.430130 0.174989 0.362112 0.074 Uiso 1 1 calc R U . . .
C8 C 0.3570(2) 0.2597(2) 0.47736(18) 0.0527(5) Uani 1 1 d . . . . .
H8 H 0.448460 0.319613 0.514404 0.063 Uiso 1 1 calc R U . . .
C9 C 0.13978(17) 0.43109(17) 0.60440(13) 0.0386(4) Uani 1 1 d . . . . .
H9 H 0.053206 0.373115 0.551132 0.046 Uiso 1 1 calc R U . . .
C10 C 0.19681(18) 0.56561(17) 0.57228(13) 0.0375(4) Uani 1 1 d . . . . .
C11 C 0.24427(17) 0.60062(17) 0.47684(13) 0.0385(4) Uani 1 1 d . . . . .
C12 C 0.2609(2) 0.5288(2) 0.38532(14) 0.0454(4) Uani 1 1 d . . . . .
H12 H 0.237448 0.436176 0.377009 0.054 Uiso 1 1 calc R U . . .
C13 C 0.3131(2) 0.5985(2) 0.30728(16) 0.0558(5) Uani 1 1 d . . . . .
H13 H 0.325143 0.551841 0.246444 0.067 Uiso 1 1 calc R U . . .
C14 C 0.3476(3) 0.7366(3) 0.31821(18) 0.0623(6) Uani 1 1 d . . . . .
H14 H 0.382479 0.780166 0.264427 0.075 Uiso 1 1 calc R U . . .
C15 C 0.3316(2) 0.8111(2) 0.40651(17) 0.0543(5) Uani 1 1 d . . . . .
H15 H 0.354163 0.903418 0.413083 0.065 Uiso 1 1 calc R U . . .
C16 C 0.27970(18) 0.74145(18) 0.48585(14) 0.0417(4) Uani 1 1 d . . . . .
C17 C 0.2933(2) 0.9318(2) 0.62429(19) 0.0571(5) Uani 1 1 d . . . . .
H17A H 0.395330 0.973078 0.655450 0.086 Uiso 1 1 calc R U . . .
H17B H 0.237207 0.939699 0.677142 0.086 Uiso 1 1 calc R U . . .
H17C H 0.272836 0.976426 0.568588 0.086 Uiso 1 1 calc R U . . .
C18 C 0.20502(18) 0.68250(17) 0.63309(13) 0.0395(4) Uani 1 1 d . . . . .
C19 C 0.1635(2) 0.6937(2) 0.73810(15) 0.0479(4) Uani 1 1 d . . . . .
H19A H 0.064144 0.689032 0.729994 0.057 Uiso 1 1 calc R U . . .
H19B H 0.227332 0.779758 0.782357 0.057 Uiso 1 1 calc R U . . .
C20 C 0.17622(19) 0.5767(2) 0.79058(14) 0.0447(4) Uani 1 1 d . . . . .
C21 C 0.09042(19) 0.44089(19) 0.71208(14) 0.0439(4) Uani 1 1 d . . . . .
H21 H -0.012518 0.428525 0.698031 0.053 Uiso 1 1 calc R U . . .
C22 C 0.1002(2) 0.3172(2) 0.75381(18) 0.0572(5) Uani 1 1 d . . . . .
H22A H 0.127625 0.337704 0.830269 0.069 Uiso 1 1 calc R U . . .
H22B H 0.006724 0.241531 0.733428 0.069 Uiso 1 1 calc R U . . .
C23 C 0.0999(2) 0.5674(2) 0.88616(16) 0.0539(5) Uani 1 1 d . . . . .
C24 C 0.3388(2) 0.6143(2) 0.95214(15) 0.0499(4) Uani 1 1 d . . . . .
C25 C 0.4678(3) 0.6513(2) 1.02298(17) 0.0595(5) Uani 1 1 d . . . . .
H25 H 0.469895 0.655570 1.095031 0.071 Uiso 1 1 calc R U . . .
C26 C 0.5942(3) 0.6819(2) 0.98277(19) 0.0617(6) Uani 1 1 d . . . . .
H26 H 0.683069 0.707298 1.028693 0.074 Uiso 1 1 calc R U . . .
C27 C 0.5912(2) 0.6754(2) 0.87598(18) 0.0573(5) Uani 1 1 d . . . . .
H27 H 0.677625 0.695548 0.850793 0.069 Uiso 1 1 calc R U . . .
C28 C 0.4595(2) 0.63893(19) 0.80530(16) 0.0480(4) Uani 1 1 d . . . . .
H28 H 0.457978 0.636087 0.733414 0.058 Uiso 1 1 calc R U . . .
C29 C 0.33192(19) 0.60720(18) 0.84328(14) 0.0437(4) Uani 1 1 d . . . . .
H2A H 0.159(4) 0.562(3) 1.039(3) 0.102(10) Uiso 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
C16 N1 C18 107.67(14) . . ?
C16 N1 C17 124.92(16) . . ?
C18 N1 C17 126.97(17) . . ?
O1 C1 C22 125.3(2) . . ?
O1 C1 C2 125.0(2) . . ?
C22 C1 C2 109.66(16) . . ?
C23 N2 C24 111.64(17) . . ?
C3 C2 C1 111.70(15) . . ?
C3 C2 C9 116.20(14) . . ?
C1 C2 C9 104.60(15) . . ?
C8 C3 C4 117.94(19) . . ?
C8 C3 C2 121.06(17) . . ?
C4 C3 C2 120.99(16) . . ?
C3 C4 C5 120.5(2) . . ?
C6 C5 C4 120.7(2) . . ?
C7 C6 C5 119.3(2) . . ?
C6 C7 C8 120.6(2) . . ?
C3 C8 C7 120.9(2) . . ?
C10 C9 C2 116.26(14) . . ?
C10 C9 C21 111.91(14) . . ?
C2 C9 C21 106.81(13) . . ?
C18 C10 C11 106.80(15) . . ?
C18 C10 C9 122.91(15) . . ?
C11 C10 C9 130.21(15) . . ?
C12 C11 C16 118.88(16) . . ?
C12 C11 C10 134.69(16) . . ?
C16 C11 C10 106.43(15) . . ?
C13 C12 C11 118.67(18) . . ?
C12 C13 C14 121.3(2) . . ?
C15 C14 C13 121.93(19) . . ?
C14 C15 C16 117.03(19) . . ?
N1 C16 C15 129.17(18) . . ?
N1 C16 C11 108.68(15) . . ?
C15 C16 C11 122.15(18) . . ?
C10 C18 N1 110.42(15) . . ?
C10 C18 C19 125.54(16) . . ?
N1 C18 C19 124.03(16) . . ?
C18 C19 C20 109.17(15) . . ?
C29 C20 C23 101.39(14) . . ?
C29 C20 C19 111.93(16) . . ?
C23 C20 C19 109.34(16) . . ?
C29 C20 C21 118.72(15) . . ?
C23 C20 C21 105.65(15) . . ?
C19 C20 C21 109.05(15) . . ?
C22 C21 C20 113.87(16) . . ?
C22 C21 C9 103.99(16) . . ?
C20 C21 C9 115.12(14) . . ?
C1 C22 C21 106.90(16) . . ?
O2 C23 N2 126.22(19) . . ?
O2 C23 C20 124.97(18) . . ?
N2 C23 C20 108.78(17) . . ?
C25 C24 C29 122.80(19) . . ?
C25 C24 N2 127.81(19) . . ?
C29 C24 N2 109.31(17) . . ?
C24 C25 C26 117.3(2) . . ?
C27 C26 C25 121.4(2) . . ?
C26 C27 C28 120.6(2) . . ?
C29 C28 C27 119.21(19) . . ?
C28 C29 C24 118.72(18) . . ?
C28 C29 C20 132.21(17) . . ?
C24 C29 C20 108.76(16) . . ?
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
O1 C1 1.210(2) . ?
N1 C16 1.379(2) . ?
N1 C18 1.388(2) . ?
N1 C17 1.449(2) . ?
C1 C22 1.491(3) . ?
C1 C2 1.539(3) . ?
O2 C23 1.218(3) . ?
N2 C23 1.351(3) . ?
N2 C24 1.402(3) . ?
C2 C3 1.511(3) . ?
C2 C9 1.547(2) . ?
C3 C8 1.385(3) . ?
C3 C4 1.387(3) . ?
C4 C5 1.389(3) . ?
C5 C6 1.370(4) . ?
C6 C7 1.367(4) . ?
C7 C8 1.386(3) . ?
C9 C10 1.495(2) . ?
C9 C21 1.552(2) . ?
C10 C18 1.373(2) . ?
C10 C11 1.436(2) . ?
C11 C12 1.401(3) . ?
C11 C16 1.418(2) . ?
C12 C13 1.388(3) . ?
C13 C14 1.389(3) . ?
C14 C15 1.380(3) . ?
C15 C16 1.401(3) . ?
C18 C19 1.485(2) . ?
C19 C20 1.549(3) . ?
C20 C29 1.516(3) . ?
C20 C23 1.541(3) . ?
C20 C21 1.551(3) . ?
C21 C22 1.536(3) . ?
C24 C25 1.376(3) . ?
C24 C29 1.400(3) . ?
C25 C26 1.381(3) . ?
C26 C27 1.378(3) . ?
C27 C28 1.396(3) . ?
C28 C29 1.377(3) . ?
