#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/52/4025245.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_4025245
loop_
_publ_author_name
'Guo-Lin Gao'
'Yan-Ning Niu'
'Ze-Yi Yan'
'Hong-Li Wang'
'Gang-Wei Wang'
'Ali Shaukat'
'Yong-Min Liang'
_publ_section_title
;
 Unexpected Domino Reaction via Pd-Catalyzed Sonogashira Coupling of
 Benzimidoyl Chlorides with 1,6-Enynes and Cyclization To Synthesize
 Quinoline Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1305
_journal_page_last               1308
_journal_paper_doi               10.1021/jo9026116
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C23 H17 N O'
_chemical_formula_weight         323.38
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 126.142(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.7675(10)
_cell_length_b                   8.4494(3)
_cell_length_c                   17.6278(8)
_cell_measurement_reflns_used    1862
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.56
_cell_measurement_theta_min      2.67
_cell_volume                     3460.2(3)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10004
_diffrn_reflns_theta_full        26.64
_diffrn_reflns_theta_max         26.64
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9769
_exptl_absorpt_correction_T_min  0.9718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0564P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1286
_reflns_number_gt                2153
_reflns_number_total             3622
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9026116_si_002.cif
_cod_data_source_block           c2c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        3460.2(2)
_cod_database_code               4025245
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.22916(6) 0.61215(18) 1.07338(11) 0.0526(4) Uani 1 1 d . . .
C2 C 0.17588(6) 0.69160(18) 1.03296(12) 0.0573(4) Uani 1 1 d . . .
H2 H 0.1694 0.7482 1.0712 0.069 Uiso 1 1 calc R . .
C3 C 0.13435(6) 0.68535(17) 0.93881(12) 0.0523(4) Uani 1 1 d . . .
C4 C 0.14484(6) 0.60256(17) 0.88072(11) 0.0511(4) Uani 1 1 d . . .
C5 C 0.10514(6) 0.58999(18) 0.78224(12) 0.0593(4) Uani 1 1 d . . .
H5 H 0.0695 0.6392 0.7524 0.071 Uiso 1 1 calc R . .
C6 C 0.11734(7) 0.5081(2) 0.72946(12) 0.0628(5) Uani 1 1 d . . .
C7 C 0.17167(7) 0.4335(2) 0.77618(13) 0.0690(5) Uani 1 1 d . . .
H7 H 0.1806 0.3764 0.7412 0.083 Uiso 1 1 calc R . .
C8 C 0.21116(7) 0.44307(19) 0.87097(13) 0.0663(5) Uani 1 1 d . . .
H8 H 0.2465 0.3925 0.8996 0.080 Uiso 1 1 calc R . .
C9 C 0.19934(6) 0.52833(17) 0.92629(11) 0.0526(4) Uani 1 1 d . . .
C10 C 0.07631(6) 0.75893(19) 0.89907(11) 0.0577(4) Uani 1 1 d . . .
C11 C 0.07017(6) 0.93165(17) 0.89161(10) 0.0490(4) Uani 1 1 d . . .
C12 C 0.11354(7) 1.02838(19) 0.90640(11) 0.0587(4) Uani 1 1 d . . .
H12 H 0.1477 0.9841 0.9219 0.070 Uiso 1 1 calc R . .
C13 C 0.10632(8) 1.1903(2) 0.89829(13) 0.0797(6) Uani 1 1 d . . .
H13 H 0.1354 1.2551 0.9075 0.096 Uiso 1 1 calc R . .
C14 C 0.05616(9) 1.2556(2) 0.87656(15) 0.0900(6) Uani 1 1 d . . .
H14 H 0.0515 1.3650 0.8721 0.108 Uiso 1 1 calc R . .
C15 C 0.01281(8) 1.1604(2) 0.86134(14) 0.0831(6) Uani 1 1 d . . .
H15 H -0.0212 1.2056 0.8461 0.100 Uiso 1 1 calc R . .
C16 C 0.01914(7) 0.9998(2) 0.86833(12) 0.0644(5) Uani 1 1 d . . .
H16 H -0.0105 0.9359 0.8576 0.077 Uiso 1 1 calc R . .
C17 C 0.27420(6) 0.61118(19) 1.17651(11) 0.0560(4) Uani 1 1 d . . .
C18 C 0.31738(7) 0.4976(2) 1.21614(13) 0.0692(5) Uani 1 1 d . . .
H18 H 0.3176 0.4223 1.1779 0.083 Uiso 1 1 calc R . .
C19 C 0.35988(8) 0.4956(3) 1.31164(15) 0.0824(6) Uani 1 1 d . . .
H19 H 0.3888 0.4196 1.3372 0.099 Uiso 1 1 calc R . .
C20 C 0.35989(8) 0.6047(3) 1.36940(14) 0.0811(6) Uani 1 1 d . . .
H20 H 0.3886 0.6026 1.4338 0.097 Uiso 1 1 calc R . .
C21 C 0.31730(8) 0.7168(2) 1.33156(13) 0.0763(5) Uani 1 1 d . . .
H21 H 0.3170 0.7904 1.3705 0.092 Uiso 1 1 calc R . .
C22 C 0.27487(7) 0.7207(2) 1.23603(12) 0.0656(5) Uani 1 1 d . . .
H22 H 0.2463 0.7977 1.2111 0.079 Uiso 1 1 calc R . .
C23 C 0.07543(8) 0.4972(2) 0.62417(12) 0.0811(6) Uani 1 1 d . . .
H23A H 0.0379 0.5285 0.6050 0.122 Uiso 1 1 calc R . .
H23B H 0.0740 0.3901 0.6047 0.122 Uiso 1 1 calc R . .
H23C H 0.0877 0.5659 0.5957 0.122 Uiso 1 1 calc R . .
N1 N 0.24025(5) 0.53324(15) 1.02113(9) 0.0556(4) Uani 1 1 d . . .
O1 O 0.03629(5) 0.67166(14) 0.87530(11) 0.1002(5) 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'
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
N1 C1 C2 121.46(14) . . ?
N1 C1 C17 117.14(13) . . ?
C2 C1 C17 121.38(15) . . ?
C3 C2 C1 120.36(15) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.68(13) . . ?
C2 C3 C10 119.03(15) . . ?
C4 C3 C10 121.18(14) . . ?
C5 C4 C3 124.44(13) . . ?
C5 C4 C9 119.07(15) . . ?
C3 C4 C9 116.49(14) . . ?
C6 C5 C4 122.10(14) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C7 118.08(15) . . ?
C5 C6 C23 122.14(15) . . ?
C7 C6 C23 119.77(16) . . ?
C8 C7 C6 121.60(16) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 120.94(15) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
N1 C9 C8 118.61(14) . . ?
N1 C9 C4 123.18(15) . . ?
C8 C9 C4 118.20(15) . . ?
O1 C10 C11 122.25(14) . . ?
O1 C10 C3 118.24(14) . . ?
C11 C10 C3 119.51(13) . . ?
C12 C11 C16 119.22(15) . . ?
C12 C11 C10 121.61(13) . . ?
C16 C11 C10 119.16(14) . . ?
C13 C12 C11 120.23(15) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 119.84(17) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 120.28(18) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 120.55(16) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 119.87(16) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
C18 C17 C22 118.04(16) . . ?
C18 C17 C1 119.70(16) . . ?
C22 C17 C1 122.26(14) . . ?
C19 C18 C17 120.59(19) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 120.59(18) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C19 119.58(18) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.30(19) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 120.89(17) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
C6 C23 H23A 109.5 . . ?
C6 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C6 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 N1 C9 118.80(12) . . ?
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 N1 1.3197(19) . ?
C1 C2 1.4210(19) . ?
C1 C17 1.485(2) . ?
C2 C3 1.359(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.412(2) . ?
C3 C10 1.512(2) . ?
C4 C5 1.411(2) . ?
C4 C9 1.4181(19) . ?
C5 C6 1.361(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.415(2) . ?
C6 C23 1.506(2) . ?
C7 C8 1.360(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.406(2) . ?
C8 H8 0.9300 . ?
C9 N1 1.3641(19) . ?
C10 O1 1.2148(18) . ?
C10 C11 1.467(2) . ?
C11 C12 1.382(2) . ?
C11 C16 1.394(2) . ?
C12 C13 1.379(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.365(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.388(2) . ?
C17 C22 1.391(2) . ?
C18 C19 1.379(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.374(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.370(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.379(2) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
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
N1 C1 C2 C3 1.3(2) . . . . ?
C17 C1 C2 C3 -177.22(14) . . . . ?
C1 C2 C3 C4 -1.5(2) . . . . ?
C1 C2 C3 C10 174.69(13) . . . . ?
C2 C3 C4 C5 -179.26(14) . . . . ?
C10 C3 C4 C5 4.6(2) . . . . ?
C2 C3 C4 C9 0.7(2) . . . . ?
C10 C3 C4 C9 -175.48(13) . . . . ?
C3 C4 C5 C6 -179.76(15) . . . . ?
C9 C4 C5 C6 0.3(2) . . . . ?
C4 C5 C6 C7 0.3(2) . . . . ?
C4 C5 C6 C23 -178.84(14) . . . . ?
C5 C6 C7 C8 -0.5(2) . . . . ?
C23 C6 C7 C8 178.72(16) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C7 C8 C9 N1 179.49(15) . . . . ?
C7 C8 C9 C4 0.7(2) . . . . ?
C5 C4 C9 N1 -179.55(14) . . . . ?
C3 C4 C9 N1 0.5(2) . . . . ?
C5 C4 C9 C8 -0.8(2) . . . . ?
C3 C4 C9 C8 179.24(13) . . . . ?
C2 C3 C10 O1 -104.05(19) . . . . ?
C4 C3 C10 O1 72.1(2) . . . . ?
C2 C3 C10 C11 75.12(19) . . . . ?
C4 C3 C10 C11 -108.72(17) . . . . ?
O1 C10 C11 C12 -170.86(17) . . . . ?
C3 C10 C11 C12 10.0(2) . . . . ?
O1 C10 C11 C16 8.7(3) . . . . ?
C3 C10 C11 C16 -170.48(14) . . . . ?
C16 C11 C12 C13 0.1(2) . . . . ?
C10 C11 C12 C13 179.59(16) . . . . ?
C11 C12 C13 C14 0.8(3) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C14 C15 C16 C11 0.3(3) . . . . ?
C12 C11 C16 C15 -0.6(2) . . . . ?
C10 C11 C16 C15 179.84(16) . . . . ?
N1 C1 C17 C18 -17.6(2) . . . . ?
C2 C1 C17 C18 160.96(15) . . . . ?
N1 C1 C17 C22 162.55(14) . . . . ?
C2 C1 C17 C22 -18.9(2) . . . . ?
C22 C17 C18 C19 -0.7(2) . . . . ?
C1 C17 C18 C19 179.42(16) . . . . ?
C17 C18 C19 C20 0.8(3) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C19 C20 C21 C22 -0.4(3) . . . . ?
C20 C21 C22 C17 0.4(3) . . . . ?
C18 C17 C22 C21 0.2(2) . . . . ?
C1 C17 C22 C21 180.00(15) . . . . ?
C2 C1 N1 C9 -0.1(2) . . . . ?
C17 C1 N1 C9 178.47(13) . . . . ?
C8 C9 N1 C1 -179.50(14) . . . . ?
C4 C9 N1 C1 -0.8(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659146
2 PubChem 45112390
