#------------------------------------------------------------------------------
#$Date: 2023-09-05 23:23:32 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286194 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/94/7159481.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_7159481
loop_
_publ_author_name
'Zhu, Chen'
'Zhou, Jubao'
'Li, Tianxing'
'Yang, Jiaxin'
'Jin, Hui'
'Zhang, Lixin'
_publ_section_title
;
 Access to 2-pyridinones comprising enaminonitriles via AgOAc
 promoted cascade reactions of thioesters with aminomethylene
 malononitriles.
;
_journal_issue                   34
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6881
_journal_page_last               6885
_journal_paper_doi               10.1039/d3ob00915g
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C12 H8 Cl N3 O'
_chemical_formula_weight         245.66
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-05-31 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.1261(7)
_cell_length_b                   7.8636(5)
_cell_length_c                   25.4825(16)
_cell_measurement_reflns_used    2047
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.42
_cell_measurement_theta_min      2.43
_cell_volume                     2229.5(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  ccd
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1092
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            15315
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.003
_diffrn_reflns_theta_max         25.003
_diffrn_reflns_theta_min         3.198
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0533
_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)+(0.0538P)²+0.9908P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1385
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1166
_reflns_number_total             1957
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00915g2.cif
_cod_data_source_block           1_a
_cod_depositor_comments          'Adding full bibliography for 7159481.cif.'
_cod_database_code               7159481
_shelx_shelxl_version_number     2014/7
_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   0.937
_shelx_estimated_absorpt_t_max   0.937
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
C1 C 0.1237(2) 0.5423(3) 0.62735(8) 0.0486(10) Uani 1 1 d G . . . .
H1 H 0.1225 0.5047 0.5928 0.058 Uiso 1 1 calc R U . . .
C2 C 0.01950(17) 0.5368(3) 0.65738(12) 0.0652(12) Uani 1 1 d G . . . .
H2 H -0.0514 0.4956 0.6429 0.078 Uiso 1 1 calc R U . . .
C3 C 0.0213(2) 0.5931(4) 0.70909(11) 0.0785(14) Uani 1 1 d G . . . .
H3 H -0.0484 0.5894 0.7292 0.094 Uiso 1 1 calc R U . . .
C4 C 0.1273(3) 0.6548(3) 0.73077(7) 0.0716(13) Uani 1 1 d G . . . .
H4 H 0.1285 0.6924 0.7654 0.086 Uiso 1 1 calc R U . . .
C5 C 0.2315(2) 0.6602(3) 0.70074(8) 0.0529(10) Uani 1 1 d G . . . .
H5 H 0.3025 0.7015 0.7152 0.063 Uiso 1 1 calc R U . . .
C6 C 0.22975(17) 0.6040(3) 0.64903(8) 0.0389(8) Uani 1 1 d G . . . .
C7 C 0.4368(3) 0.5209(4) 0.64056(14) 0.0408(9) Uani 1 1 d . . . . .
H7 H 0.4287 0.4631 0.6722 0.049 Uiso 1 1 calc R U . . .
C8 C 0.5455(3) 0.5239(4) 0.61679(13) 0.0395(9) Uani 1 1 d . . . . .
C9 C 0.5597(3) 0.6097(4) 0.56728(13) 0.0393(9) Uani 1 1 d . . . . .
C10 C 0.4582(3) 0.6819(4) 0.54589(13) 0.0391(8) Uani 1 1 d . . . . .
C11 C 0.3438(3) 0.6809(4) 0.57033(13) 0.0392(8) Uani 1 1 d . . . . .
C12 C 0.6452(3) 0.4347(5) 0.63963(15) 0.0516(10) Uani 1 1 d . . . . .
Cl1 Cl 0.46768(8) 0.78360(12) 0.48631(3) 0.0525(3) Uani 1 1 d . . . . .
N1 N 0.3391(2) 0.5992(3) 0.61977(10) 0.0380(7) Uani 1 1 d . . . . .
N2 N 0.7261(3) 0.3655(5) 0.65653(14) 0.0747(11) Uani 1 1 d . . . . .
N3 N 0.6687(2) 0.6150(4) 0.54437(11) 0.0539(9) Uani 1 1 d . . . . .
H3A H 0.6777 0.6656 0.5147 0.065 Uiso 1 1 calc R U . . .
H3B H 0.7293 0.5678 0.5594 0.065 Uiso 1 1 calc R U . . .
O1 O 0.2520(2) 0.7498(3) 0.55324(9) 0.0511(7) Uani 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'
Cl Cl 0.1484 0.1585 '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 C1 C6 120.0 . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 N1 119.43(19) . . ?
C1 C6 N1 120.43(19) . . ?
C8 C7 N1 122.2(3) . . ?
C8 C7 H7 118.9 . . ?
N1 C7 H7 118.9 . . ?
C7 C8 C12 120.0(3) . . ?
C7 C8 C9 119.9(3) . . ?
C12 C8 C9 120.0(3) . . ?
N3 C9 C10 123.7(3) . . ?
N3 C9 C8 119.5(3) . . ?
C10 C9 C8 116.8(3) . . ?
C9 C10 C11 124.1(3) . . ?
C9 C10 Cl1 119.4(3) . . ?
C11 C10 Cl1 116.5(3) . . ?
O1 C11 N1 118.9(3) . . ?
O1 C11 C10 125.8(3) . . ?
N1 C11 C10 115.3(3) . . ?
N2 C12 C8 178.0(4) . . ?
C7 N1 C11 121.6(3) . . ?
C7 N1 C6 119.4(3) . . ?
C11 N1 C6 119.0(3) . . ?
C9 N3 H3A 120.0 . . ?
C9 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
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
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 H1 0.9300 . ?
C2 C3 1.3900 . ?
C2 H2 0.9300 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 N1 1.428(3) . ?
C7 C8 1.353(4) . ?
C7 N1 1.357(4) . ?
C7 H7 0.9300 . ?
C8 C12 1.435(5) . ?
C8 C9 1.439(5) . ?
C9 N3 1.346(4) . ?
C9 C10 1.376(4) . ?
C10 C11 1.418(5) . ?
C10 Cl1 1.719(3) . ?
C11 O1 1.236(4) . ?
C11 N1 1.415(4) . ?
C12 N2 1.137(4) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
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
C6 C1 C2 C3 0.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C4 C5 C6 N1 -175.7(2) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C2 C1 C6 N1 175.6(2) . . . . ?
N1 C7 C8 C12 -178.2(3) . . . . ?
N1 C7 C8 C9 -1.2(5) . . . . ?
C7 C8 C9 N3 178.7(3) . . . . ?
C12 C8 C9 N3 -4.3(5) . . . . ?
C7 C8 C9 C10 -1.6(5) . . . . ?
C12 C8 C9 C10 175.4(3) . . . . ?
N3 C9 C10 C11 -178.3(3) . . . . ?
C8 C9 C10 C11 2.0(5) . . . . ?
N3 C9 C10 Cl1 0.7(5) . . . . ?
C8 C9 C10 Cl1 -178.9(3) . . . . ?
C9 C10 C11 O1 177.1(3) . . . . ?
Cl1 C10 C11 O1 -1.9(5) . . . . ?
C9 C10 C11 N1 0.2(5) . . . . ?
Cl1 C10 C11 N1 -178.8(2) . . . . ?
C8 C7 N1 C11 3.6(5) . . . . ?
C8 C7 N1 C6 -174.5(3) . . . . ?
O1 C11 N1 C7 179.8(3) . . . . ?
C10 C11 N1 C7 -3.1(4) . . . . ?
O1 C11 N1 C6 -2.1(4) . . . . ?
C10 C11 N1 C6 175.1(3) . . . . ?
C5 C6 N1 C7 50.9(3) . . . . ?
C1 C6 N1 C7 -124.7(3) . . . . ?
C5 C6 N1 C11 -127.2(2) . . . . ?
C1 C6 N1 C11 57.1(3) . . . . ?
