#------------------------------------------------------------------------------
#$Date: 2025-08-22 13:33:34 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301861 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/73/7157357.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_7157357
loop_
_publ_author_name
'Dong, Shanliang'
'Huang, Jingjing'
'Sha, Hongkai'
'Qiu, Lihua'
'Hu, Wenhao'
'Xu, Xinfang'
_publ_section_title
;
 Copper-catalyzed formal [1 + 2 + 2]-annulation of alkyne-tethered
 diazoacetates and pyridines: access to polycyclic indolizines.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1926
_journal_page_last               1932
_journal_paper_doi               10.1039/d0ob00222d
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C21 H15 N O'
_chemical_formula_weight         297.34
_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
;
2019-01-09 deposited with the CCDC.	2020-02-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.097(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4156(5)
_cell_length_b                   14.0062(6)
_cell_length_c                   11.1540(6)
_cell_measurement_reflns_used    6771
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.38
_cell_volume                     1426.66(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0657
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23104
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_min         2.663
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3268
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0402
_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)+(0.0237P)²+0.9819P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.1001
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2589
_reflns_number_total             3268
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00222d2.cif
_cod_data_source_block           DSL190107C
_cod_depositor_comments
'Adding full bibliography for 7157357--7157358.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7157357
_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.
;
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 0.85276(11) 0.50726(7) 0.84200(9) 0.0232(2) Uani 1 1 d . . . . .
N1 N 0.78819(13) 0.48328(8) 0.47008(11) 0.0182(3) Uani 1 1 d . . . . .
C16 C 0.55497(15) 0.68052(10) 0.53427(13) 0.0192(3) Uani 1 1 d . . . . .
C4 C 0.71639(15) 0.53863(10) 0.63315(13) 0.0189(3) Uani 1 1 d . . . . .
C3 C 0.79806(15) 0.46821(10) 0.59448(13) 0.0183(3) Uani 1 1 d . . . . .
C1 C 0.90674(15) 0.42335(10) 0.80532(13) 0.0195(3) Uani 1 1 d . . . . .
C2 C 0.88174(15) 0.39882(10) 0.67932(13) 0.0191(3) Uani 1 1 d . . . . .
C14 C 0.69544(15) 0.56221(10) 0.43026(13) 0.0184(3) Uani 1 1 d . . . . .
C12 C 0.72274(16) 0.53595(11) 0.22353(14) 0.0225(3) Uani 1 1 d . . . . .
H12 H 0.698564 0.551555 0.138072 0.027 Uiso 1 1 calc R U . . .
C17 C 0.55682(16) 0.76016(11) 0.45892(14) 0.0224(3) Uani 1 1 d . . . . .
H17 H 0.622891 0.761658 0.406750 0.027 Uiso 1 1 calc R U . . .
C15 C 0.65120(15) 0.59819(10) 0.53322(13) 0.0183(3) Uani 1 1 d . . . . .
C13 C 0.66151(16) 0.58547(10) 0.30343(14) 0.0212(3) Uani 1 1 d . . . . .
H13 H 0.595342 0.636149 0.273396 0.025 Uiso 1 1 calc R U . . .
C9 C 0.94047(16) 0.31233(11) 0.65063(14) 0.0224(3) Uani 1 1 d . . . . .
H9 H 0.920933 0.291929 0.566980 0.027 Uiso 1 1 calc R U . . .
C6 C 0.99353(16) 0.36773(11) 0.89680(14) 0.0227(3) Uani 1 1 d . . . . .
H6 H 1.011104 0.386544 0.980972 0.027 Uiso 1 1 calc R U . . .
C21 C 0.45862(16) 0.68221(11) 0.61234(14) 0.0210(3) Uani 1 1 d . . . . .
H21 H 0.456060 0.629486 0.665353 0.025 Uiso 1 1 calc R U . . .
C11 C 0.82293(16) 0.46085(11) 0.26876(14) 0.0221(3) Uani 1 1 d . . . . .
H11 H 0.868305 0.427786 0.213660 0.027 Uiso 1 1 calc R U . . .
C20 C 0.36705(16) 0.75954(11) 0.61346(14) 0.0225(3) Uani 1 1 d . . . . .
H20 H 0.303231 0.759604 0.667597 0.027 Uiso 1 1 calc R U . . .
C10 C 0.85427(16) 0.43602(10) 0.38946(13) 0.0204(3) Uani 1 1 d . . . . .
H10 H 0.921875 0.385969 0.418872 0.024 Uiso 1 1 calc R U . . .
C19 C 0.36815(17) 0.83678(11) 0.53595(14) 0.0241(3) Uani 1 1 d . . . . .
H19 H 0.303922 0.889171 0.535460 0.029 Uiso 1 1 calc R U . . .
C18 C 0.46404(17) 0.83682(11) 0.45908(14) 0.0244(3) Uani 1 1 d . . . . .
H18 H 0.465992 0.889764 0.406263 0.029 Uiso 1 1 calc R U . . .
C5 C 0.71404(16) 0.53992(11) 0.76626(13) 0.0218(3) Uani 1 1 d . . . . .
H5A H 0.694463 0.605627 0.790760 0.026 Uiso 1 1 calc R U . . .
H5B H 0.634421 0.498077 0.779346 0.026 Uiso 1 1 calc R U . . .
C7 C 1.05503(16) 0.28405(11) 0.86500(14) 0.0244(3) Uani 1 1 d . . . . .
H7 H 1.116394 0.246187 0.927304 0.029 Uiso 1 1 calc R U . . .
C8 C 1.02668(16) 0.25598(11) 0.74234(14) 0.0243(3) Uani 1 1 d . . . . .
H8 H 1.066452 0.197891 0.720963 0.029 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
C1 O1 C5 116.18(11) . . ?
C10 N1 C3 130.46(13) . . ?
C10 N1 C14 120.85(12) . . ?
C3 N1 C14 108.67(11) . . ?
C17 C16 C21 117.65(13) . . ?
C17 C16 C15 121.55(13) . . ?
C21 C16 C15 120.80(13) . . ?
C3 C4 C15 110.13(13) . . ?
C3 C4 C5 117.63(13) . . ?
C15 C4 C5 132.24(13) . . ?
C4 C3 N1 107.30(12) . . ?
C4 C3 C2 122.02(13) . . ?
N1 C3 C2 130.57(13) . . ?
O1 C1 C6 117.06(13) . . ?
O1 C1 C2 121.23(13) . . ?
C6 C1 C2 121.59(14) . . ?
C9 C2 C1 117.33(13) . . ?
C9 C2 C3 127.83(13) . . ?
C1 C2 C3 114.83(13) . . ?
C15 C14 C13 134.12(14) . . ?
C15 C14 N1 107.89(12) . . ?
C13 C14 N1 117.91(13) . . ?
C13 C12 C11 119.64(14) . . ?
C18 C17 C16 121.16(14) . . ?
C14 C15 C4 105.98(12) . . ?
C14 C15 C16 126.43(13) . . ?
C4 C15 C16 127.59(13) . . ?
C12 C13 C14 120.64(14) . . ?
C8 C9 C2 121.09(14) . . ?
C1 C6 C7 119.65(14) . . ?
C20 C21 C16 121.10(14) . . ?
C10 C11 C12 120.60(14) . . ?
C21 C20 C19 120.33(14) . . ?
C11 C10 N1 120.11(14) . . ?
C20 C19 C18 119.35(14) . . ?
C17 C18 C19 120.39(14) . . ?
O1 C5 C4 110.34(12) . . ?
C8 C7 C6 119.93(14) . . ?
C7 C8 C9 120.27(14) . . ?
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 1.3813(17) . ?
O1 C5 1.4462(17) . ?
N1 C10 1.3807(18) . ?
N1 C3 1.3841(18) . ?
N1 C14 1.4118(18) . ?
C16 C17 1.399(2) . ?
C16 C21 1.402(2) . ?
C16 C15 1.468(2) . ?
C4 C3 1.383(2) . ?
C4 C15 1.408(2) . ?
C4 C5 1.490(2) . ?
C3 C2 1.448(2) . ?
C1 C6 1.382(2) . ?
C1 C2 1.410(2) . ?
C2 C9 1.401(2) . ?
C14 C15 1.4069(19) . ?
C14 C13 1.410(2) . ?
C12 C13 1.363(2) . ?
C12 C11 1.421(2) . ?
C17 C18 1.384(2) . ?
C9 C8 1.387(2) . ?
C6 C7 1.391(2) . ?
C21 C20 1.386(2) . ?
C11 C10 1.352(2) . ?
C20 C19 1.386(2) . ?
C19 C18 1.388(2) . ?
C7 C8 1.386(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168353284
