#------------------------------------------------------------------------------
#$Date: 2026-02-18 01:14:55 +0100 (Wed 18 de Feb de 2026) $
#$Revision: 304497 $
#$URL: svn://www.crystallography.net/cod/cif/7/72/02/7720221.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_7720221
loop_
_publ_author_name
'Zhang, Guoqi'
'Mei, Haiyu'
'Kanina, Amy'
'Chocho, Marilyn'
'Hiyaev, Paulina'
'Cheng, Shu-Yuan'
'Neary, Michelle C.'
_publ_section_title
;
 Isomers of 2,2':6',2″-terpyridine and 2,6-dipyrazin-2-ylpyridine
 with aliphatic substituents: synthesis, coordination chemistry, and
 catalytic and anticancer activities.
;
_journal_issue                   7
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2855
_journal_page_last               2867
_journal_paper_doi               10.1039/d5dt02824h
_journal_volume                  55
_journal_year                    2026
_chemical_formula_sum            'C17 H17 N5'
_chemical_formula_weight         291.36
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2025-10-22 deposited with the CCDC.	2026-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3655(18)
_cell_length_b                   6.9938(8)
_cell_length_c                   16.633(2)
_cell_measurement_reflns_used    4325
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.88
_cell_volume                     1554.8(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 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker cmos'
_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  0.0623
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7469
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         3.16
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9845
_exptl_absorpt_correction_T_min  0.9769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1548
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0591
_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)+(0.0816P)²+0.2794P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1473
_refine_ls_wR_factor_ref         0.1744
_reflns_number_gt                906
_reflns_number_total             1548
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d5dt02824h2.cif
_cod_data_source_block           umd579
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               7720221
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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 0.5571(2) 0.7500 0.47826(18) 0.0482(8) Uani 1 2 d S . .
HA H 0.5631 0.7500 0.4226 0.058 Uiso 1 2 calc SR . .
C2 C 0.4636(2) 0.7500 0.51383(18) 0.0471(8) Uani 1 2 d S . .
C3 C 0.5323(3) 0.7500 0.64066(18) 0.0533(9) Uani 1 2 d S . .
C4 C 0.6282(2) 0.7500 0.60929(17) 0.0510(8) Uani 1 2 d S . .
H4A H 0.6833 0.7500 0.6434 0.061 Uiso 1 2 calc SR . .
C5 C 0.6416(2) 0.7500 0.52616(16) 0.0442(8) Uani 1 2 d S . .
C6 C 0.7440(2) 0.7500 0.49189(18) 0.0488(8) Uani 1 2 d S . .
C7 C 0.9116(3) 0.7500 0.5086(2) 0.0905(14) Uani 1 2 d S . .
H7A H 0.9672 0.7500 0.5423 0.109 Uiso 1 2 calc SR . .
C8 C 0.9266(3) 0.7500 0.4288(2) 0.0988(15) Uani 1 2 d S . .
H8A H 0.9917 0.7500 0.4091 0.119 Uiso 1 2 calc SR . .
C9 C 0.7613(3) 0.7500 0.4107(2) 0.0851(13) Uani 1 2 d S . .
H9A H 0.7063 0.7500 0.3765 0.102 Uiso 1 2 calc SR . .
C10 C 0.3726(2) 0.7500 0.46318(19) 0.0497(8) Uani 1 2 d S . .
C11 C 0.2771(3) 0.7500 0.4969(2) 0.0672(10) Uani 1 2 d S . .
H11A H 0.2712 0.7500 0.5526 0.081 Uiso 1 2 calc SR . .
C12 C 0.2084(3) 0.7500 0.3737(3) 0.0805(12) Uani 1 2 d S . .
H12A H 0.1529 0.7500 0.3400 0.097 Uiso 1 2 calc SR . .
C13 C 0.3021(3) 0.7500 0.3397(2) 0.0758(11) Uani 1 2 d S . .
H13A H 0.3080 0.7500 0.2840 0.091 Uiso 1 2 calc SR . .
C14 C 0.5104(3) 0.7500 0.73150(18) 0.0645(10) Uani 1 2 d S . .
C15 C 0.6072(3) 0.7500 0.7810(2) 0.0969(15) Uani 1 2 d S . .
H15A H 0.6456 0.6379 0.7683 0.145 Uiso 0.50 1 calc PR . .
H15B H 0.5911 0.7500 0.8372 0.145 Uiso 1 2 calc SR . .
H15C H 0.6456 0.8621 0.7683 0.145 Uiso 0.50 1 calc PR . .
C16 C 0.4506(2) 0.5711(4) 0.75150(14) 0.0933(10) Uani 1 1 d . . .
H16A H 0.4892 0.4599 0.7380 0.140 Uiso 1 1 calc R . .
H16B H 0.3895 0.5709 0.7212 0.140 Uiso 1 1 calc R . .
H16C H 0.4355 0.5696 0.8079 0.140 Uiso 1 1 calc R . .
N1 N 0.4508(2) 0.7500 0.59371(16) 0.0546(7) Uani 1 2 d S . .
N2 N 0.8212(2) 0.7500 0.54160(16) 0.0760(10) Uani 1 2 d S . .
N3 N 0.8519(3) 0.7500 0.37794(19) 0.1074(14) Uani 1 2 d S . .
N4 N 0.1938(2) 0.7500 0.4529(2) 0.0818(10) Uani 1 2 d S . .
N5 N 0.3842(2) 0.7500 0.38410(16) 0.0613(8) Uani 1 2 d S . .
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'
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
C5 C1 C2 119.5(3) . . ?
C5 C1 HA 120.3 . . ?
C2 C1 HA 120.3 . . ?
N1 C2 C1 122.7(3) . . ?
N1 C2 C10 117.4(3) . . ?
C1 C2 C10 120.0(3) . . ?
N1 C3 C4 122.2(3) . . ?
N1 C3 C14 114.6(3) . . ?
C4 C3 C14 123.1(3) . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 H4A 120.2 . . ?
C5 C4 H4A 120.2 . . ?
C1 C5 C4 117.8(3) . . ?
C1 C5 C6 122.2(3) . . ?
C4 C5 C6 120.0(3) . . ?
N2 C6 C9 118.9(3) . . ?
N2 C6 C5 118.7(3) . . ?
C9 C6 C5 122.4(3) . . ?
N2 C7 C8 123.0(4) . . ?
N2 C7 H7A 118.5 . . ?
C8 C7 H7A 118.5 . . ?
N3 C8 C7 121.7(4) . . ?
N3 C8 H8A 119.1 . . ?
C7 C8 H8A 119.1 . . ?
N3 C9 C6 124.0(3) . . ?
N3 C9 H9A 118.0 . . ?
C6 C9 H9A 118.0 . . ?
N5 C10 C11 120.4(3) . . ?
N5 C10 C2 118.0(3) . . ?
C11 C10 C2 121.6(3) . . ?
N4 C11 C10 123.0(4) . . ?
N4 C11 H11A 118.5 . . ?
C10 C11 H11A 118.5 . . ?
N4 C12 C13 122.8(4) . . ?
N4 C12 H12A 118.6 . . ?
C13 C12 H12A 118.6 . . ?
N5 C13 C12 121.7(4) . . ?
N5 C13 H13A 119.1 . . ?
C12 C13 H13A 119.1 . . ?
C16 C14 C16 110.7(3) . 7_575 ?
C16 C14 C15 108.99(19) . . ?
C16 C14 C15 108.99(19) 7_575 . ?
C16 C14 C3 108.34(19) . . ?
C16 C14 C3 108.34(19) 7_575 . ?
C15 C14 C3 111.5(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C2 N1 C3 118.3(3) . . ?
C6 N2 C7 116.9(3) . . ?
C8 N3 C9 115.5(3) . . ?
C12 N4 C11 114.9(3) . . ?
C13 N5 C10 117.2(3) . . ?
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 C5 1.382(4) . ?
C1 C2 1.383(4) . ?
C1 HA 0.9300 . ?
C2 N1 1.340(4) . ?
C2 C10 1.479(4) . ?
C3 N1 1.341(4) . ?
C3 C4 1.384(4) . ?
C3 C14 1.539(4) . ?
C4 C5 1.394(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.482(4) . ?
C6 N2 1.323(4) . ?
C6 C9 1.370(4) . ?
C7 N2 1.327(4) . ?
C7 C8 1.343(5) . ?
C7 H7A 0.9300 . ?
C8 N3 1.308(5) . ?
C8 H8A 0.9300 . ?
C9 N3 1.328(4) . ?
C9 H9A 0.9300 . ?
C10 N5 1.324(4) . ?
C10 C11 1.395(4) . ?
C11 N4 1.332(4) . ?
C11 H11A 0.9300 . ?
C12 N4 1.332(5) . ?
C12 C13 1.374(5) . ?
C12 H12A 0.9300 . ?
C13 N5 1.323(4) . ?
C13 H13A 0.9300 . ?
C14 C16 1.521(3) . ?
C14 C16 1.521(3) 7_575 ?
C14 C15 1.534(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C5 C1 C2 N1 0.0 . . . . ?
C5 C1 C2 C10 180.0 . . . . ?
N1 C3 C4 C5 0.0 . . . . ?
C14 C3 C4 C5 180.0 . . . . ?
C2 C1 C5 C4 0.0 . . . . ?
C2 C1 C5 C6 180.0 . . . . ?
C3 C4 C5 C1 0.0 . . . . ?
C3 C4 C5 C6 180.0 . . . . ?
C1 C5 C6 N2 180.0 . . . . ?
C4 C5 C6 N2 0.0 . . . . ?
C1 C5 C6 C9 0.0 . . . . ?
C4 C5 C6 C9 180.0 . . . . ?
N2 C7 C8 N3 0.0 . . . . ?
N2 C6 C9 N3 0.0 . . . . ?
C5 C6 C9 N3 180.0 . . . . ?
N1 C2 C10 N5 180.0 . . . . ?
C1 C2 C10 N5 0.0 . . . . ?
N1 C2 C10 C11 0.0 . . . . ?
C1 C2 C10 C11 180.0 . . . . ?
N5 C10 C11 N4 0.0 . . . . ?
C2 C10 C11 N4 180.0 . . . . ?
N4 C12 C13 N5 0.0 . . . . ?
N1 C3 C14 C16 60.1(2) . . . . ?
C4 C3 C14 C16 -119.9(2) . . . . ?
N1 C3 C14 C16 -60.1(2) . . . 7_575 ?
C4 C3 C14 C16 119.9(2) . . . 7_575 ?
N1 C3 C14 C15 180.0 . . . . ?
C4 C3 C14 C15 0.000(1) . . . . ?
C1 C2 N1 C3 0.0 . . . . ?
C10 C2 N1 C3 180.0 . . . . ?
C4 C3 N1 C2 0.0 . . . . ?
C14 C3 N1 C2 180.0 . . . . ?
C9 C6 N2 C7 0.0 . . . . ?
C5 C6 N2 C7 180.0 . . . . ?
C8 C7 N2 C6 0.0 . . . . ?
C7 C8 N3 C9 0.0 . . . . ?
C6 C9 N3 C8 0.0 . . . . ?
C13 C12 N4 C11 0.0 . . . . ?
C10 C11 N4 C12 0.0 . . . . ?
C12 C13 N5 C10 0.0 . . . . ?
C11 C10 N5 C13 0.0 . . . . ?
C2 C10 N5 C13 180.0 . . . . ?
