#------------------------------------------------------------------------------
#$Date: 2021-11-24 11:52:27 +0200 (Wed, 24 Nov 2021) $
#$Revision: 270855 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/53/1565392.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_1565392
loop_
_publ_author_name
'Nwachukwu, Chideraa I.'
'Bosch, Eric'
_publ_section_title
;
 Synthesis of 4-[(2-imidazylethynyl)]-5-(2-pyridylethynyl)veratrole and
 characterization of the coordination complexes with silver(I) and
 palladium(II)
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119328
_journal_paper_doi               10.1016/j.ica.2019.119328
_journal_volume                  502
_journal_year                    2020
_chemical_formula_sum            'C20 H15 N3 O2'
_chemical_formula_weight         329.35
_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_hydrogens   mixed
_cell_angle_alpha                110.387(6)
_cell_angle_beta                 95.185(6)
_cell_angle_gamma                92.835(7)
_cell_formula_units_Z            2
_cell_length_a                   6.698(3)
_cell_length_b                   9.659(4)
_cell_length_c                   13.379(6)
_cell_measurement_reflns_used    1097
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.15
_cell_measurement_theta_min      2.26
_cell_volume                     805.0(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'XSeed (Barbour, 2001)'
_computing_publication_material  'XSeed (Barbour, 2001)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3660
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega 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  0.0593
_diffrn_reflns_av_unetI/netI     0.0791
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10255
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.142
_diffrn_reflns_theta_min         2.258
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014(Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       'cut block'
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3575
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1278
_refine_ls_R_factor_gt           0.0648
_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)+(0.1110P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1648
_refine_ls_wR_factor_ref         0.2067
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1868
_reflns_number_total             3575
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ICA-2020-502-119328.cif
_cod_data_source_block           eb608_a
_cod_original_cell_volume        804.9(6)
_cod_database_code               1565392
_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, -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
O1 O 0.7411(3) 0.6788(2) 0.42643(15) 0.0311(5) Uani 1 1 d . . . . .
N1 N 0.7632(3) 0.5200(3) 1.00272(18) 0.0287(6) Uani 1 1 d . . . . .
C1 C 0.7469(4) 0.5446(3) 1.1062(2) 0.0312(7) Uani 1 1 d . . . . .
H1 H 0.772854 0.466613 1.132130 0.037 Uiso 1 1 calc R U . . .
O2 O 0.7284(3) 0.3981(2) 0.31432(14) 0.0305(5) Uani 1 1 d . . . . .
N2 N 0.8231(4) 0.2167(3) 0.88451(19) 0.0290(6) Uani 1 1 d D . . . .
C2 C 0.6951(5) 0.6756(4) 1.1777(2) 0.0334(7) Uani 1 1 d . . . . .
H2 H 0.685494 0.687062 1.250539 0.040 Uiso 1 1 calc R U . . .
N3 N 0.8192(4) -0.0086(3) 0.75970(19) 0.0338(6) Uani 1 1 d . . . . .
C3 C 0.6576(4) 0.7890(3) 1.1411(2) 0.0328(7) Uani 1 1 d . . . . .
H3 H 0.621901 0.880844 1.188535 0.039 Uiso 1 1 calc R U . . .
C4 C 0.6723(4) 0.7680(3) 1.0337(2) 0.0298(7) Uani 1 1 d . . . . .
H4 H 0.646667 0.845126 1.006744 0.036 Uiso 1 1 calc R U . . .
C5 C 0.7252(4) 0.6325(3) 0.9667(2) 0.0281(7) Uani 1 1 d . . . . .
C6 C 0.7440(4) 0.6032(3) 0.8551(2) 0.0281(7) Uani 1 1 d . . . . .
C7 C 0.7568(4) 0.5763(3) 0.7615(2) 0.0282(7) Uani 1 1 d . . . . .
C8 C 0.7600(4) 0.5309(3) 0.6473(2) 0.0263(7) Uani 1 1 d . . . . .
C9 C 0.7532(4) 0.6340(3) 0.5948(2) 0.0275(7) Uani 1 1 d . . . . .
H9 H 0.753235 0.736664 0.635373 0.033 Uiso 1 1 calc R U . . .
C10 C 0.7464(4) 0.5866(3) 0.4834(2) 0.0269(7) Uani 1 1 d . . . . .
C11 C 0.7424(4) 0.4348(3) 0.4234(2) 0.0276(7) Uani 1 1 d . . . . .
C12 C 0.7549(4) 0.3327(3) 0.4746(2) 0.0265(6) Uani 1 1 d . . . . .
H12 H 0.758256 0.230561 0.433532 0.032 Uiso 1 1 calc R U . . .
C13 C 0.7625(4) 0.3794(3) 0.5870(2) 0.0259(6) Uani 1 1 d . . . . .
C14 C 0.7773(4) 0.2771(3) 0.6426(2) 0.0293(7) Uani 1 1 d . . . . .
C15 C 0.7914(4) 0.2046(3) 0.6993(2) 0.0303(7) Uani 1 1 d . . . . .
C16 C 0.8124(4) 0.1356(3) 0.7777(2) 0.0290(7) Uani 1 1 d . . . . .
C17 C 0.8388(4) 0.1193(3) 0.9369(2) 0.0318(7) Uani 1 1 d . . . . .
H17 H 0.849422 0.142510 1.012325 0.038 Uiso 1 1 calc R U . . .
C18 C 0.8364(5) -0.0164(3) 0.8614(2) 0.0344(7) Uani 1 1 d . . . . .
H18 H 0.845343 -0.105499 0.875975 0.041 Uiso 1 1 calc R U . . .
C19 C 0.7503(5) 0.8334(3) 0.4853(2) 0.0356(8) Uani 1 1 d . . . . .
H19A H 0.631273 0.855735 0.523701 0.053 Uiso 1 1 calc R U . . .
H19B H 0.754170 0.887816 0.435775 0.053 Uiso 1 1 calc R U . . .
H19C H 0.871854 0.863233 0.536994 0.053 Uiso 1 1 calc R U . . .
C20 C 0.7039(5) 0.2438(3) 0.2516(2) 0.0351(7) Uani 1 1 d . . . . .
H20A H 0.826762 0.197966 0.263703 0.053 Uiso 1 1 calc R U . . .
H20B H 0.678198 0.230507 0.175421 0.053 Uiso 1 1 calc R U . . .
H20C H 0.590065 0.196750 0.272625 0.053 Uiso 1 1 calc R U . . .
H2N H 0.820(5) 0.318(2) 0.918(2) 0.050(11) Uiso 1 1 d 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
C10 O1 C19 117.3(2) . .
C1 N1 C5 117.2(2) . .
N1 C1 C2 124.3(3) . .
N1 C1 H1 117.8 . .
C2 C1 H1 117.8 . .
C11 O2 C20 116.4(2) . .
C17 N2 C16 106.7(3) . .
C17 N2 H2N 125(2) . .
C16 N2 H2N 129(2) . .
C3 C2 C1 118.3(3) . .
C3 C2 H2 120.8 . .
C1 C2 H2 120.8 . .
C16 N3 C18 103.9(2) . .
C2 C3 C4 119.3(3) . .
C2 C3 H3 120.4 . .
C4 C3 H3 120.4 . .
C5 C4 C3 118.9(3) . .
C5 C4 H4 120.6 . .
C3 C4 H4 120.6 . .
N1 C5 C4 122.0(3) . .
N1 C5 C6 116.0(2) . .
C4 C5 C6 121.9(3) . .
C7 C6 C5 178.7(3) . .
C6 C7 C8 174.4(3) . .
C9 C8 C13 119.7(3) . .
C9 C8 C7 121.4(3) . .
C13 C8 C7 118.9(2) . .
C10 C9 C8 120.3(3) . .
C10 C9 H9 119.8 . .
C8 C9 H9 119.8 . .
O1 C10 C9 124.1(3) . .
O1 C10 C11 116.1(2) . .
C9 C10 C11 119.8(3) . .
O2 C11 C12 124.0(3) . .
O2 C11 C10 115.7(2) . .
C12 C11 C10 120.3(3) . .
C11 C12 C13 120.4(3) . .
C11 C12 H12 119.8 . .
C13 C12 H12 119.8 . .
C8 C13 C12 119.5(3) . .
C8 C13 C14 118.7(2) . .
C12 C13 C14 121.9(3) . .
C15 C14 C13 172.8(3) . .
C14 C15 C16 172.8(3) . .
N3 C16 N2 111.8(3) . .
N3 C16 C15 127.1(3) . .
N2 C16 C15 121.1(3) . .
C18 C17 N2 106.9(3) . .
C18 C17 H17 126.6 . .
N2 C17 H17 126.6 . .
C17 C18 N3 110.8(3) . .
C17 C18 H18 124.6 . .
N3 C18 H18 124.6 . .
O1 C19 H19A 109.5 . .
O1 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
O1 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
O2 C20 H20A 109.5 . .
O2 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
O2 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C10 1.359(3) .
O1 C19 1.420(3) .
N1 C1 1.336(4) .
N1 C5 1.359(4) .
C1 C2 1.377(4) .
C1 H1 0.9500 .
O2 C11 1.370(3) .
O2 C20 1.425(3) .
N2 C17 1.357(4) .
N2 C16 1.363(4) .
N2 H2N 0.922(18) .
C2 C3 1.371(4) .
C2 H2 0.9500 .
N3 C16 1.331(4) .
N3 C18 1.384(4) .
C3 C4 1.394(4) .
C3 H3 0.9500 .
C4 C5 1.388(4) .
C4 H4 0.9500 .
C5 C6 1.439(4) .
C6 C7 1.198(4) .
C7 C8 1.438(4) .
C8 C9 1.405(4) .
C8 C13 1.405(4) .
C9 C10 1.393(4) .
C9 H9 0.9500 .
C10 C11 1.402(4) .
C11 C12 1.384(4) .
C12 C13 1.408(4) .
C12 H12 0.9500 .
C13 C14 1.430(4) .
C14 C15 1.200(4) .
C15 C16 1.426(4) .
C17 C18 1.345(4) .
C17 H17 0.9500 .
C18 H18 0.9500 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 O1 0.95 2.38 3.303(4) 164.2 1_556 yes
C9 H9 N3 0.95 2.43 3.369(4) 167.7 1_565 yes
N2 H2N N1 0.922(18) 1.97(2) 2.872(4) 167(3) . yes
