#------------------------------------------------------------------------------
#$Date: 2025-07-06 19:58:36 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 301166 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/04/7160488.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_7160488
loop_
_publ_author_name
'Gao, Ying'
'Peng, Ju-Yin'
'Zhang, Yu-Na'
'Zhao, Xiao-Liang'
'Zhao, Yu-Long'
_publ_section_title
;
 A copper-catalyzed tandem cyclization reaction of N-acyl enamines
 and electron-deficient alkynes: direct synthesis of alkynyl substituted
 pyridines.
;
_journal_issue                   18
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4441
_journal_page_last               4445
_journal_paper_doi               10.1039/d5ob00390c
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C21 N2 O4'
_chemical_formula_sum            'C21 N2 O4'
_chemical_formula_weight         344.23
_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_primary     dual
_audit_creation_date             2021-12-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-03-04 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                96.900(10)
_cell_angle_beta                 104.419(11)
_cell_angle_gamma                106.168(10)
_cell_formula_units_Z            2
_cell_length_a                   8.6618(18)
_cell_length_b                   9.7333(19)
_cell_length_c                   12.207(3)
_cell_measurement_reflns_used    7181
_cell_measurement_temperature    278(2)
_cell_measurement_theta_max      25.127
_cell_measurement_theta_min      1.628
_cell_volume                     937.2(4)
_computing_cell_refinement       'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015b)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      278.4
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Quazar'
_diffrn_measurement_method       '0.5° ω and 0.5° φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       'Bruker APEX II'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15872
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        63.886
_diffrn_reflns_theta_max         63.886
_diffrn_reflns_theta_min         4.832
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.231
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0916
_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)+(0.2000P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2639
_refine_ls_wR_factor_ref         0.2858
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2380
_reflns_number_total             3082
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ob00390c2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7160488.cif.'
_cod_original_cell_volume        937.2(3)
_cod_database_code               7160488
_shelx_shelxl_version_number     2016/4
_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   0.867
_shelx_estimated_absorpt_t_min   0.843
_olex2_refinement_description
;
;
_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
O001 O 0.5766(3) 0.9721(2) 0.76407(19) 0.0609(7) Uani 1 1 d . . . . .
N002 N 0.5037(3) 0.6841(2) 0.3755(2) 0.0398(6) Uani 1 1 d . . . . .
O003 O 0.9927(3) 1.3298(3) 0.7853(2) 0.0752(8) Uani 1 1 d . . . . .
O004 O 0.3797(4) 0.7645(3) 0.7518(2) 0.0806(10) Uani 1 1 d . . . . .
O005 O 1.0166(4) 1.3411(3) 0.6080(3) 0.0805(9) Uani 1 1 d . . . . .
C006 C 0.3895(3) 0.6060(3) 0.4218(2) 0.0372(7) Uani 1 1 d . . . . .
C007 C 0.6097(3) 0.8750(3) 0.5458(2) 0.0372(7) Uani 1 1 d . . . . .
C008 C 0.2741(3) 0.4630(3) 0.3505(2) 0.0385(7) Uani 1 1 d . . . . .
C009 C 0.4934(4) 0.7938(3) 0.5941(2) 0.0398(7) Uani 1 1 d . . . . .
C00A C 0.3833(4) 0.6582(3) 0.5313(3) 0.0417(7) Uani 1 1 d . . . . .
C00B C 0.6102(3) 0.8130(3) 0.4352(2) 0.0393(7) Uani 1 1 d . . . . .
C00C C 0.7289(3) 1.0163(3) 0.6004(3) 0.0413(7) Uani 1 1 d . . . . .
C00D C 0.0617(4) 0.1919(3) 0.2163(3) 0.0466(8) Uani 1 1 d . . . . .
C00E C 0.8320(4) 1.1351(3) 0.6369(3) 0.0474(8) Uani 1 1 d . . . . .
C00F C 0.9569(4) 1.2782(3) 0.6732(3) 0.0481(8) Uani 1 1 d . . . . .
N00G N -0.1371(4) -0.0607(3) 0.0967(3) 0.0760(10) Uani 1 1 d . . . . .
C00H C 0.2884(4) 0.4137(3) 0.2424(3) 0.0518(8) Uani 1 1 d . . . . .
C00I C 0.4763(4) 0.8399(3) 0.7119(3) 0.0463(8) Uani 1 1 d . . . . .
C00J C 0.1514(4) 0.3758(3) 0.3894(3) 0.0489(8) Uani 1 1 d . . . . .
C00K C 0.1831(4) 0.2784(4) 0.1753(3) 0.0564(9) Uani 1 1 d . . . . .
C00L C 0.0456(4) 0.2405(3) 0.3231(3) 0.0515(8) Uani 1 1 d . . . . .
C00M C 0.7354(4) 0.8926(4) 0.3786(3) 0.0579(9) Uani 1 1 d . . . . .
C00N C -0.0479(4) 0.0506(4) 0.1491(3) 0.0574(9) Uani 1 1 d . . . . .
C00O C 0.5690(5) 1.0246(4) 0.8799(3) 0.0695(11) Uani 1 1 d . . . . .
C00P C 1.2876(6) 1.4543(5) 0.8807(6) 0.1113(19) Uani 1 1 d . . . . .
C00Q C 1.1222(6) 1.4724(4) 0.8346(4) 0.0897(14) Uani 1 1 d . . . . .
C00R C 0.6871(8) 1.1793(5) 0.9194(4) 0.1019(18) 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C00I O001 C00O 116.1(3) . . ?
C00B N002 C006 119.4(2) . . ?
C00F O003 C00Q 117.5(3) . . ?
N002 C006 C008 116.7(2) . . ?
N002 C006 C00A 121.1(3) . . ?
C00A C006 C008 122.2(3) . . ?
C009 C007 C00B 117.7(2) . . ?
C009 C007 C00C 124.8(3) . . ?
C00B C007 C00C 117.5(3) . . ?
C00H C008 C006 120.0(3) . . ?
C00J C008 C006 121.1(3) . . ?
C00J C008 C00H 118.9(3) . . ?
C007 C009 C00I 125.4(3) . . ?
C00A C009 C007 119.0(3) . . ?
C00A C009 C00I 115.6(3) . . ?
C009 C00A C006 119.8(3) . . ?
N002 C00B C007 122.9(3) . . ?
N002 C00B C00M 116.3(3) . . ?
C007 C00B C00M 120.8(3) . . ?
C00E C00C C007 174.1(3) . . ?
C00K C00D C00N 120.7(3) . . ?
C00L C00D C00K 120.1(3) . . ?
C00L C00D C00N 119.2(3) . . ?
C00C C00E C00F 176.3(3) . . ?
O003 C00F C00E 111.8(3) . . ?
O005 C00F O003 125.4(3) . . ?
O005 C00F C00E 122.8(3) . . ?
C00K C00H C008 120.7(3) . . ?
O001 C00I C009 112.7(3) . . ?
O004 C00I O001 124.0(3) . . ?
O004 C00I C009 123.3(3) . . ?
C008 C00J C00L 120.8(3) . . ?
C00H C00K C00D 119.5(3) . . ?
C00D C00L C00J 119.9(3) . . ?
N00G C00N C00D 178.6(4) . . ?
O001 C00O C00R 106.5(3) . . ?
O003 C00Q C00P 110.4(4) . . ?
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
O001 C00I 1.312(4) . ?
O001 C00O 1.469(4) . ?
N002 C006 1.355(4) . ?
N002 C00B 1.326(3) . ?
O003 C00F 1.326(4) . ?
O003 C00Q 1.464(4) . ?
O004 C00I 1.193(4) . ?
O005 C00F 1.192(4) . ?
C006 C008 1.482(4) . ?
C006 C00A 1.392(4) . ?
C007 C009 1.396(4) . ?
C007 C00B 1.413(4) . ?
C007 C00C 1.432(4) . ?
C008 C00H 1.396(4) . ?
C008 C00J 1.386(4) . ?
C009 C00A 1.389(4) . ?
C009 C00I 1.510(4) . ?
C00B C00M 1.512(4) . ?
C00C C00E 1.198(4) . ?
C00D C00K 1.392(5) . ?
C00D C00L 1.387(5) . ?
C00D C00N 1.441(4) . ?
C00E C00F 1.443(4) . ?
N00G C00N 1.141(4) . ?
C00H C00K 1.391(4) . ?
C00J C00L 1.389(4) . ?
C00O C00R 1.507(5) . ?
C00P C00Q 1.471(7) . ?
