#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/59/7155965.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_7155965
loop_
_publ_author_name
'Shiri, Morteza'
'Ranjbar, Maryam'
'Yasaei, Zahra'
'Zamanian, Fatemeh'
'Notash, Behrouz'
_publ_section_title
;
 Palladium-catalyzed tandem reaction of 2-chloroquinoline-3-carbaldehydes
 and isocyanides
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/C7OB02043K
_journal_year                    2017
_chemical_formula_moiety         'C21 H20 N2 O2'
_chemical_formula_sum            'C21 H20 N2 O2'
_chemical_formula_weight         332.39
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-03-26 deposited with the CCDC.
2017-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 112.46(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.937(3)
_cell_length_b                   8.9523(18)
_cell_length_c                   12.934(3)
_cell_measurement_reflns_used    3006
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.66
_cell_volume                     1705.4(7)
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_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  0.0877
_diffrn_reflns_av_sigmaI/netI    0.0818
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8780
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.66
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0124(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.858
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3006
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.858
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0476
_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)+(0.0560P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1175
_reflns_number_gt                1788
_reflns_number_total             3006
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob02043k2.cif
_cod_data_source_block           khd392h
_cod_original_cell_volume        1705.4(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7155965
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O -0.00459(10) 1.0305(2) 0.27980(13) 0.0673(5) Uani 1 1 d .
O2 O -0.12892(10) 0.66070(17) 0.04018(14) 0.0566(4) Uani 1 1 d .
N1 N 0.13987(11) 0.9049(2) 0.20838(13) 0.0467(5) Uani 1 1 d .
N2 N -0.09933(11) 0.90050(19) 0.12681(13) 0.0461(5) Uani 1 1 d .
C1 C 0.32952(15) 0.9297(3) 0.30765(18) 0.0648(7) Uani 1 1 d .
H1 H 0.2942 0.9844 0.3371 0.078 Uiso 1 1 calc R
C2 C 0.42229(18) 0.9364(4) 0.3573(2) 0.0859(9) Uani 1 1 d .
H2 H 0.4495 0.9970 0.4196 0.103 Uiso 1 1 calc R
C3 C 0.47615(18) 0.8542(4) 0.3158(2) 0.0875(9) Uani 1 1 d .
H3 H 0.5390 0.8575 0.3515 0.105 Uiso 1 1 calc R
C4 C 0.43711(17) 0.7689(3) 0.2231(2) 0.0742(7) Uani 1 1 d .
H4 H 0.4737 0.7145 0.1954 0.089 Uiso 1 1 calc R
C5 C 0.34242(15) 0.7615(3) 0.16840(18) 0.0564(6) Uani 1 1 d .
C6 C 0.28801(14) 0.8412(3) 0.21344(16) 0.0493(5) Uani 1 1 d .
C7 C 0.18993(13) 0.8317(2) 0.15967(15) 0.0441(5) Uani 1 1 d .
C8 C 0.15113(15) 0.7453(2) 0.06115(16) 0.0488(5) Uani 1 1 d .
C9 C 0.20880(16) 0.6734(3) 0.01509(19) 0.0618(6) Uani 1 1 d .
H9 H 0.1833 0.6219 -0.0522 0.074 Uiso 1 1 calc R
C10 C 0.30017(17) 0.6793(3) 0.0680(2) 0.0649(7) Uani 1 1 d .
H10 H 0.3362 0.6281 0.0378 0.078 Uiso 1 1 calc R
C11 C 0.05553(15) 0.7329(2) 0.01193(16) 0.0512(6) Uani 1 1 d .
H11 H 0.0273 0.6775 -0.0530 0.061 Uiso 1 1 calc R
C12 C 0.00647(14) 0.8041(2) 0.06219(15) 0.0445(5) Uani 1 1 d .
C13 C 0.05114(14) 0.8883(2) 0.15786(15) 0.0435(5) Uani 1 1 d .
C14 C -0.01710(14) 0.9513(2) 0.19830(16) 0.0466(5) Uani 1 1 d .
C15 C -0.09394(13) 0.8036(2) 0.03847(15) 0.0469(5) Uani 1 1 d .
H15 H -0.1269 0.8499 -0.0345 0.056 Uiso 1 1 calc R
C16 C -0.18377(14) 0.9337(3) 0.14293(17) 0.0508(6) Uani 1 1 d .
H16 H -0.1781 1.0350 0.1736 0.061 Uiso 1 1 calc R
C17 C -0.19780(16) 0.8296(3) 0.22674(18) 0.0693(7) Uani 1 1 d .
H17A H -0.1464 0.8370 0.2975 0.083 Uiso 1 1 calc R
H17B H -0.2010 0.7275 0.2003 0.083 Uiso 1 1 calc R
C18 C -0.28419(18) 0.8667(4) 0.2445(2) 0.0870(9) Uani 1 1 d .
H18A H -0.2941 0.7919 0.2929 0.104 Uiso 1 1 calc R
H18B H -0.2769 0.9625 0.2820 0.104 Uiso 1 1 calc R
C19 C -0.36618(17) 0.8730(4) 0.1366(2) 0.0806(8) Uani 1 1 d .
H19A H -0.3799 0.7734 0.1051 0.097 Uiso 1 1 calc R
H19B H -0.4180 0.9080 0.1516 0.097 Uiso 1 1 calc R
C20 C -0.35102(17) 0.9747(3) 0.0537(2) 0.0760(8) Uani 1 1 d .
H20A H -0.3456 1.0767 0.0808 0.091 Uiso 1 1 calc R
H20B H -0.4030 0.9697 -0.0166 0.091 Uiso 1 1 calc R
C21 C -0.26561(14) 0.9323(3) 0.03435(18) 0.0600(7) Uani 1 1 d .
H21A H -0.2730 0.8335 0.0013 0.072 Uiso 1 1 calc R
H21B H -0.2564 1.0024 -0.0176 0.072 Uiso 1 1 calc R
H2A H -0.0943(17) 0.616(3) 0.108(2) 0.086(9) Uiso 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
C15 O2 H2A 108.1(16)
C13 N1 C7 115.09(17)
C14 N2 C15 113.58(16)
C14 N2 C16 122.17(16)
C15 N2 C16 124.14(16)
C2 C1 C6 120.2(2)
C2 C1 H1 119.9
C6 C1 H1 119.9
C1 C2 C3 120.9(3)
C1 C2 H2 119.6
C3 C2 H2 119.6
C4 C3 C2 119.9(2)
C4 C3 H3 120.0
C2 C3 H3 120.0
C3 C4 C5 121.0(3)
C3 C4 H4 119.5
C5 C4 H4 119.5
C4 C5 C6 118.8(2)
C4 C5 C10 122.0(2)
C6 C5 C10 119.3(2)
C1 C6 C5 119.2(2)
C1 C6 C7 121.2(2)
C5 C6 C7 119.5(2)
N1 C7 C8 123.29(18)
N1 C7 C6 117.74(18)
C8 C7 C6 118.95(19)
C11 C8 C7 118.27(19)
C11 C8 C9 122.17(19)
C7 C8 C9 119.6(2)
C10 C9 C8 120.8(2)
C10 C9 H9 119.6
C8 C9 H9 119.6
C9 C10 C5 121.8(2)
C9 C10 H10 119.1
C5 C10 H10 119.1
C12 C11 C8 117.93(19)
C12 C11 H11 121.0
C8 C11 H11 121.0
C11 C12 C13 119.32(19)
C11 C12 C15 131.59(19)
C13 C12 C15 108.96(17)
N1 C13 C12 126.08(19)
N1 C13 C14 124.94(17)
C12 C13 C14 108.91(17)
O1 C14 N2 125.26(19)
O1 C14 C13 128.57(18)
N2 C14 C13 106.15(16)
O2 C15 N2 112.78(16)
O2 C15 C12 113.38(17)
N2 C15 C12 102.33(15)
O2 C15 H15 109.4
N2 C15 H15 109.4
C12 C15 H15 109.4
N2 C16 C21 112.30(16)
N2 C16 C17 111.83(18)
C21 C16 C17 110.55(19)
N2 C16 H16 107.3
C21 C16 H16 107.3
C17 C16 H16 107.3
C16 C17 C18 111.4(2)
C16 C17 H17A 109.3
C18 C17 H17A 109.3
C16 C17 H17B 109.3
C18 C17 H17B 109.3
H17A C17 H17B 108.0
C19 C18 C17 112.7(2)
C19 C18 H18A 109.1
C17 C18 H18A 109.1
C19 C18 H18B 109.1
C17 C18 H18B 109.1
H18A C18 H18B 107.8
C20 C19 C18 111.5(2)
C20 C19 H19A 109.3
C18 C19 H19A 109.3
C20 C19 H19B 109.3
C18 C19 H19B 109.3
H19A C19 H19B 108.0
C19 C20 C21 111.5(2)
C19 C20 H20A 109.3
C21 C20 H20A 109.3
C19 C20 H20B 109.3
C21 C20 H20B 109.3
H20A C20 H20B 108.0
C16 C21 C20 110.73(18)
C16 C21 H21A 109.5
C20 C21 H21A 109.5
C16 C21 H21B 109.5
C20 C21 H21B 109.5
H21A C21 H21B 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C14 1.222(2)
O2 C15 1.399(2)
O2 H2A 0.93(3)
N1 C13 1.320(3)
N1 C7 1.359(3)
N2 C14 1.361(3)
N2 C15 1.463(2)
N2 C16 1.469(3)
C1 C2 1.370(3)
C1 C6 1.390(3)
C1 H1 0.9300
C2 C3 1.385(4)
C2 H2 0.9300
C3 C4 1.355(4)
C3 H3 0.9300
C4 C5 1.402(3)
C4 H4 0.9300
C5 C6 1.409(3)
C5 C10 1.419(3)
C6 C7 1.450(3)
C7 C8 1.415(3)
C8 C11 1.414(3)
C8 C9 1.425(3)
C9 C10 1.353(3)
C9 H9 0.9300
C10 H10 0.9300
C11 C12 1.352(3)
C11 H11 0.9300
C12 C13 1.391(3)
C12 C15 1.510(3)
C13 C14 1.486(3)
C15 H15 0.9800
C16 C21 1.508(3)
C16 C17 1.510(3)
C16 H16 0.9800
C17 C18 1.516(3)
C17 H17A 0.9700
C17 H17B 0.9700
C18 C19 1.505(4)
C18 H18A 0.9700
C18 H18B 0.9700
C19 C20 1.494(3)
C19 H19A 0.9700
C19 H19B 0.9700
C20 C21 1.523(3)
C20 H20A 0.9700
C20 H20B 0.9700
C21 H21A 0.9700
C21 H21B 0.9700
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
C6 C1 C2 C3 -0.9(4)
C1 C2 C3 C4 1.9(5)
C2 C3 C4 C5 -0.4(4)
C3 C4 C5 C6 -1.8(4)
C3 C4 C5 C10 176.6(3)
C2 C1 C6 C5 -1.4(4)
C2 C1 C6 C7 179.8(2)
C4 C5 C6 C1 2.7(3)
C10 C5 C6 C1 -175.8(2)
C4 C5 C6 C7 -178.4(2)
C10 C5 C6 C7 3.1(3)
C13 N1 C7 C8 0.9(3)
C13 N1 C7 C6 -177.88(18)
C1 C6 C7 N1 -4.0(3)
C5 C6 C7 N1 177.16(18)
C1 C6 C7 C8 177.2(2)
C5 C6 C7 C8 -1.6(3)
N1 C7 C8 C11 -0.9(3)
C6 C7 C8 C11 177.82(19)
N1 C7 C8 C9 179.4(2)
C6 C7 C8 C9 -1.9(3)
C11 C8 C9 C10 -175.6(2)
C7 C8 C9 C10 4.0(3)
C8 C9 C10 C5 -2.6(4)
C4 C5 C10 C9 -179.5(2)
C6 C5 C10 C9 -1.0(4)
C7 C8 C11 C12 -0.3(3)
C9 C8 C11 C12 179.4(2)
C8 C11 C12 C13 1.3(3)
C8 C11 C12 C15 -174.0(2)
C7 N1 C13 C12 0.3(3)
C7 N1 C13 C14 176.96(18)
C11 C12 C13 N1 -1.5(3)
C15 C12 C13 N1 174.86(19)
C11 C12 C13 C14 -178.55(18)
C15 C12 C13 C14 -2.2(2)
C15 N2 C14 O1 -178.1(2)
C16 N2 C14 O1 -1.7(3)
C15 N2 C14 C13 0.7(2)
C16 N2 C14 C13 177.03(17)
N1 C13 C14 O1 2.6(4)
C12 C13 C14 O1 179.7(2)
N1 C13 C14 N2 -176.11(19)
C12 C13 C14 N2 1.0(2)
C14 N2 C15 O2 120.26(18)
C16 N2 C15 O2 -56.0(2)
C14 N2 C15 C12 -1.9(2)
C16 N2 C15 C12 -178.19(17)
C11 C12 C15 O2 56.4(3)
C13 C12 C15 O2 -119.29(19)
C11 C12 C15 N2 178.2(2)
C13 C12 C15 N2 2.5(2)
C14 N2 C16 C21 153.2(2)
C15 N2 C16 C21 -30.9(3)
C14 N2 C16 C17 -81.9(3)
C15 N2 C16 C17 94.1(2)
N2 C16 C17 C18 178.9(2)
C21 C16 C17 C18 -55.2(3)
C16 C17 C18 C19 53.2(3)
C17 C18 C19 C20 -52.6(4)
C18 C19 C20 C21 54.3(3)
N2 C16 C21 C20 -177.24(19)
C17 C16 C21 C20 57.1(3)
C19 C20 C21 C16 -57.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139193285
