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#$Date: 2024-07-05 20:24:05 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293165 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/78/7247856.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_7247856
loop_
_publ_author_name
'Zeng, Kui'
'Pandit, Neeraj Kumar'
'Oliveira, João C. A.'
'Dechert, Sebastian'
'Ackermann, Lutz'
'Zhang, Kai'
_publ_section_title
;
 Weak-coordination-auxiliary aminocatalysis enables directed [3 + 2]
 cyclization for 2-acylindolizines
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              5253
_journal_page_last               5259
_journal_paper_doi               10.1039/D3GC03552B
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C13 H15 N O'
_chemical_formula_sum            'C13 H15 N O'
_chemical_formula_weight         201.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-10-12 deposited with the CCDC.	2023-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.317(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5190(13)
_cell_length_b                   12.050(2)
_cell_length_c                   11.678(2)
_cell_measurement_reflns_used    155
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.1858
_cell_measurement_theta_min      2.4498
_cell_volume                     1041.0(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.10'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2012)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1020
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_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            31200
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.885
_diffrn_reflns_theta_min         2.449
_diffrn_source                   'Microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS, 2016)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0505
_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)+(0.0516P)²+0.5691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1372
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1762
_reflns_number_total             2483
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3gc03552b2.cif
_cod_data_source_block           kui1366_21
_cod_depositor_comments
'Adding full bibliography for 7247855--7247856.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7247856
_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   0.972
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.32576(18) 0.25470(11) 0.65553(11) 0.0323(3) Uani 1 1 d . . . . .
N1 N 0.31888(19) 0.59003(13) 0.55837(12) 0.0247(3) Uani 1 1 d . . . . .
C1 C 0.2636(2) 0.40909(15) 0.53121(14) 0.0232(4) Uani 1 1 d . . . . .
C2 C 0.3477(2) 0.48875(15) 0.61072(14) 0.0229(4) Uani 1 1 d . . . . .
C3 C 0.3715(2) 0.69489(15) 0.60042(15) 0.0263(4) Uani 1 1 d . . . . .
H3 H 0.439430 0.703304 0.676750 0.032 Uiso 1 1 calc R U . . .
C4 C 0.3259(2) 0.78529(16) 0.53247(16) 0.0292(4) Uani 1 1 d . . . . .
H4 H 0.361634 0.857017 0.561634 0.035 Uiso 1 1 calc R U . . .
C5 C 0.2245(3) 0.77365(16) 0.41736(16) 0.0304(4) Uani 1 1 d . . . . .
H5 H 0.194310 0.837314 0.369881 0.037 Uiso 1 1 calc R U . . .
C6 C 0.1715(2) 0.67164(16) 0.37611(16) 0.0278(4) Uani 1 1 d . . . . .
H6 H 0.103424 0.664202 0.299709 0.033 Uiso 1 1 calc R U . . .
C7 C 0.2163(2) 0.57628(15) 0.44535(14) 0.0217(4) Uani 1 1 d . . . . .
C8 C 0.1824(2) 0.46483(15) 0.42699(14) 0.0238(4) Uani 1 1 d . . . . .
C9 C 0.4520(2) 0.47696(16) 0.73133(15) 0.0274(4) Uani 1 1 d . . . . .
H9A H 0.526483 0.409796 0.736334 0.041 Uiso 1 1 calc R U . . .
H9B H 0.368013 0.471450 0.786291 0.041 Uiso 1 1 calc R U . . .
H9C H 0.530095 0.541897 0.750631 0.041 Uiso 1 1 calc R U . . .
C10 C 0.0738(2) 0.42077(16) 0.31614(15) 0.0291(4) Uani 1 1 d . . . . .
H10A H 0.026617 0.482855 0.265485 0.044 Uiso 1 1 calc R U . . .
H10B H -0.027099 0.376426 0.333861 0.044 Uiso 1 1 calc R U . . .
H10C H 0.150944 0.374219 0.276578 0.044 Uiso 1 1 calc R U . . .
C11 C 0.2649(2) 0.28977(16) 0.55752(15) 0.0255(4) Uani 1 1 d . . . . .
C12 C 0.1886(2) 0.20884(16) 0.46222(15) 0.0272(4) Uani 1 1 d . . . . .
H12A H 0.245688 0.222749 0.393496 0.033 Uiso 1 1 calc R U . . .
H12B H 0.057211 0.222398 0.438859 0.033 Uiso 1 1 calc R U . . .
C13 C 0.2183(3) 0.08828(16) 0.49852(16) 0.0338(5) Uani 1 1 d . . . . .
H13A H 0.164897 0.040005 0.433914 0.051 Uiso 1 1 calc R U . . .
H13B H 0.160987 0.073581 0.566029 0.051 Uiso 1 1 calc R U . . .
H13C H 0.348286 0.073443 0.519047 0.051 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
C2 N1 C3 130.06(15) . . ?
C2 N1 C7 109.24(14) . . ?
C3 N1 C7 120.69(15) . . ?
C2 C1 C8 108.36(16) . . ?
C2 C1 C11 123.02(16) . . ?
C8 C1 C11 128.61(16) . . ?
N1 C2 C1 107.37(15) . . ?
N1 C2 C9 121.52(15) . . ?
C1 C2 C9 131.12(16) . . ?
C4 C3 N1 119.91(16) . . ?
C3 C4 C5 120.56(18) . . ?
C6 C5 C4 119.83(17) . . ?
C5 C6 C7 120.72(17) . . ?
C8 C7 C6 133.38(16) . . ?
C8 C7 N1 108.33(15) . . ?
C6 C7 N1 118.28(16) . . ?
C7 C8 C1 106.69(15) . . ?
C7 C8 C10 122.50(16) . . ?
C1 C8 C10 130.79(17) . . ?
O1 C11 C1 121.23(17) . . ?
O1 C11 C12 119.48(17) . . ?
C1 C11 C12 119.29(15) . . ?
C11 C12 C13 113.18(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 C11 1.229(2) . ?
N1 C2 1.365(2) . ?
N1 C3 1.387(2) . ?
N1 C7 1.414(2) . ?
C1 C2 1.405(2) . ?
C1 C8 1.428(2) . ?
C1 C11 1.470(3) . ?
C2 C9 1.491(2) . ?
C3 C4 1.355(3) . ?
C4 C5 1.429(3) . ?
C5 C6 1.354(3) . ?
C6 C7 1.411(3) . ?
C7 C8 1.377(3) . ?
C8 C10 1.498(2) . ?
C11 C12 1.513(3) . ?
C12 C13 1.519(3) . ?
