#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/55/2215587.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2215587
loop_
_publ_author_name
'Kwak, Han'
'Park, Chi-Ho'
'Kim, Pan-Gi'
'Kim, Cheal'
'Kim, Youngmee'
_publ_section_title
;
 4,5-Dimethyl-1,2-bis(pyridine-3-carboxamido)benzene
;
_journal_coeditor_code           LH2501
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4104
_journal_page_last               o4105
_journal_paper_doi               10.1107/S1600536807044492
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C20 H18 N4 O2'
_chemical_formula_moiety         'C20 H18 N4 O2'
_chemical_formula_sum            'C20 H18 N4 O2'
_chemical_formula_weight         346.38
_chemical_name_systematic
;
4,5-Dimethyl-1,2-bis(pyridine-3-carboxamido)benzene
;
_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           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 101.467(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.086(2)
_cell_length_b                   17.960(5)
_cell_length_c                   12.135(3)
_cell_measurement_reflns_used    1519
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.57
_cell_measurement_theta_min      2.27
_cell_volume                     1727.1(8)
_computing_cell_refinement       'SMART (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  'SHELXTL (Bruker, 1998)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9503
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.155
_refine_ls_extinction_coef       0.0233(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3391
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0429
_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)+(0.0396P)²+0.2189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1108
_reflns_number_gt                2300
_reflns_number_total             3391
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2501.cif
_cod_data_source_block           I
_cod_original_cell_volume        1727.2(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2215587
_cod_database_fobs_code          2215587
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N1 0.5376(2) 0.74635(9) 0.34859(15) 0.0654(5) Uani d . 1
N N2 0.28726(18) 0.52612(8) 0.46355(13) 0.0414(4) Uani d . 1
H H2N 0.356(2) 0.5308(10) 0.5311(17) 0.054(5) Uiso d . 1
N N3 0.16193(17) 0.45162(7) 0.64598(11) 0.0395(3) Uani d . 1
H H3N 0.069(2) 0.4465(9) 0.6770(14) 0.048(5) Uiso d . 1
N N4 0.1892(2) 0.45996(12) 0.99772(15) 0.0791(6) Uani d . 1
O O1 0.16797(14) 0.58349(6) 0.29969(9) 0.0481(3) Uani d . 1
O O2 0.42842(14) 0.49969(7) 0.68104(10) 0.0513(3) Uani d . 1
C C1 0.4360(2) 0.68713(10) 0.33456(16) 0.0535(5) Uani d . 1
H H1 0.3927 0.6719 0.2612 0.064 Uiso calc R 1
C C2 0.5950(3) 0.76727(11) 0.45490(19) 0.0619(5) Uani d . 1
H H2 0.6652 0.8087 0.4676 0.074 Uiso calc R 1
C C3 0.5569(2) 0.73150(10) 0.54635(17) 0.0566(5) Uani d . 1
H H3 0.6001 0.7486 0.6187 0.068 Uiso calc R 1
C C4 0.4536(2) 0.66975(9) 0.52960(16) 0.0496(5) Uani d . 1
H H4 0.4272 0.6442 0.5905 0.060 Uiso calc R 1
C C5 0.3900(2) 0.64649(9) 0.42080(14) 0.0408(4) Uani d . 1
C C6 0.2720(2) 0.58253(9) 0.38911(14) 0.0402(4) Uani d . 1
C C7 0.19937(19) 0.45736(9) 0.44661(14) 0.0381(4) Uani d . 1
C C8 0.1681(2) 0.42332(9) 0.34149(14) 0.0458(4) Uani d . 1
H H8 0.2085 0.4458 0.2830 0.055 Uiso calc R 1
C C9 0.0792(2) 0.35732(10) 0.32058(14) 0.0468(4) Uani d . 1
C C10 0.0223(2) 0.32184(9) 0.40926(15) 0.0452(4) Uani d . 1
C C11 0.0582(2) 0.35489(9) 0.51430(14) 0.0424(4) Uani d . 1
H H11 0.0227 0.3312 0.5737 0.051 Uiso calc R 1
C C12 0.14512(19) 0.42190(8) 0.53512(13) 0.0363(4) Uani d . 1
C C13 0.2963(2) 0.48389(9) 0.71203(14) 0.0391(4) Uani d . 1
C C14 0.2776(2) 0.49965(9) 0.82949(14) 0.0403(4) Uani d . 1
C C15 0.3483(2) 0.56311(10) 0.88388(16) 0.0549(5) Uani d . 1
H H15 0.4049 0.5970 0.8468 0.066 Uiso calc R 1
C C16 0.3339(3) 0.57546(12) 0.99318(17) 0.0670(6) Uani d . 1
H H16 0.3776 0.6185 1.0306 0.080 Uiso calc R 1
C C17 0.2542(3) 0.52323(14) 1.04615(19) 0.0740(6) Uani d . 1
H H17 0.2447 0.5322 1.1201 0.089 Uiso calc R 1
C C18 0.1988(2) 0.45048(11) 0.89029(16) 0.0588(5) Uani d . 1
H H18 0.1495 0.4081 0.8538 0.071 Uiso calc R 1
C C19 0.0500(3) 0.32368(11) 0.20413(17) 0.0689(6) Uani d . 1
H H19A 0.0737 0.3602 0.1516 0.103 Uiso calc R 1
H H19B -0.0654 0.3079 0.1827 0.103 Uiso calc R 1
H H19C 0.1231 0.2816 0.2041 0.103 Uiso calc R 1
C C20 -0.0709(3) 0.24884(10) 0.39309(19) 0.0696(6) Uani d . 1
H H20A -0.0907 0.2315 0.4642 0.104 Uiso calc R 1
H H20B -0.0045 0.2128 0.3627 0.104 Uiso calc R 1
H H20C -0.1769 0.2556 0.3421 0.104 Uiso calc R 1
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
C1 N1 C2 115.76(17)
C6 N2 C7 125.53(15)
C6 N2 H2N 120.0(12)
C7 N2 H2N 114.5(12)
C13 N3 C12 129.50(14)
C13 N3 H3N 115.5(11)
C12 N3 H3N 114.9(11)
C18 N4 C17 116.35(19)
N1 C1 C5 125.06(18)
N1 C1 H1 117.5
C5 C1 H1 117.5
N1 C2 C3 124.06(18)
N1 C2 H2 118.0
C3 C2 H2 118.0
C2 C3 C4 119.02(18)
C2 C3 H3 120.5
C4 C3 H3 120.5
C3 C4 C5 118.88(17)
C3 C4 H4 120.6
C5 C4 H4 120.6
C4 C5 C1 117.21(16)
C4 C5 C6 125.11(15)
C1 C5 C6 117.65(15)
O1 C6 N2 123.77(15)
O1 C6 C5 120.29(15)
N2 C6 C5 115.94(15)
C8 C7 C12 118.58(15)
C8 C7 N2 120.63(15)
C12 C7 N2 120.78(14)
C9 C8 C7 122.53(16)
C9 C8 H8 118.7
C7 C8 H8 118.7
C8 C9 C10 119.05(15)
C8 C9 C19 119.53(16)
C10 C9 C19 121.40(17)
C11 C10 C9 118.08(15)
C11 C10 C20 120.10(16)
C9 C10 C20 121.80(16)
C10 C11 C12 122.98(15)
C10 C11 H11 118.5
C12 C11 H11 118.5
C11 C12 C7 118.73(15)
C11 C12 N3 116.38(14)
C7 C12 N3 124.75(14)
O2 C13 N3 124.23(15)
O2 C13 C14 120.41(15)
N3 C13 C14 115.36(14)
C15 C14 C18 117.49(16)
C15 C14 C13 120.17(15)
C18 C14 C13 122.24(16)
C16 C15 C14 119.24(18)
C16 C15 H15 120.4
C14 C15 H15 120.4
C17 C16 C15 118.8(2)
C17 C16 H16 120.6
C15 C16 H16 120.6
N4 C17 C16 123.8(2)
N4 C17 H17 118.1
C16 C17 H17 118.1
N4 C18 C14 124.24(19)
N4 C18 H18 117.9
C14 C18 H18 117.9
C9 C19 H19A 109.5
C9 C19 H19B 109.5
H19A C19 H19B 109.5
C9 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C10 C20 H20A 109.5
C10 C20 H20B 109.5
H20A C20 H20B 109.5
C10 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
N1 C1 1.334(2)
N1 C2 1.335(3)
N2 C6 1.347(2)
N2 C7 1.419(2)
N2 H2N 0.90(2)
N3 C13 1.346(2)
N3 C12 1.428(2)
N3 H3N 0.907(17)
N4 C18 1.332(2)
N4 C17 1.338(3)
O1 C6 1.2340(19)
O2 C13 1.2345(19)
C1 C5 1.386(2)
C1 H1 0.9300
C2 C3 1.369(3)
C2 H2 0.9300
C3 C4 1.379(2)
C3 H3 0.9300
C4 C5 1.383(2)
C4 H4 0.9300
C5 C6 1.494(2)
C7 C8 1.392(2)
C7 C12 1.392(2)
C8 C9 1.383(2)
C8 H8 0.9300
C9 C10 1.404(2)
C9 C19 1.512(2)
C10 C11 1.384(2)
C10 C20 1.506(2)
C11 C12 1.391(2)
C11 H11 0.9300
C13 C14 1.490(2)
C14 C15 1.382(2)
C14 C18 1.384(2)
C15 C16 1.372(3)
C15 H15 0.9300
C16 C17 1.369(3)
C16 H16 0.9300
C17 H17 0.9300
C18 H18 0.9300
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C8 H8 O1 . 0.93 2.51 2.921(2) 107.2
N2 H2N O2 . 0.90(2) 1.88(2) 2.701(2) 150.8(16)
C17 H17 O1 1_556 0.93 2.55 3.461(3) 165.3
N3 H3N O1 3_566 0.907(17) 2.066(18) 2.9407(19) 161.6(15)
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
C2 N1 C1 C5 -1.1(3)
C1 N1 C2 C3 0.7(3)
N1 C2 C3 C4 0.3(3)
C2 C3 C4 C5 -0.8(3)
C3 C4 C5 C1 0.4(2)
C3 C4 C5 C6 -177.68(15)
N1 C1 C5 C4 0.6(3)
N1 C1 C5 C6 178.84(17)
C7 N2 C6 O1 6.3(3)
C7 N2 C6 C5 -174.10(13)
C4 C5 C6 O1 148.83(17)
C1 C5 C6 O1 -29.3(2)
C4 C5 C6 N2 -30.8(2)
C1 C5 C6 N2 151.08(16)
C6 N2 C7 C8 37.4(2)
C6 N2 C7 C12 -143.67(16)
C12 C7 C8 C9 2.8(2)
N2 C7 C8 C9 -178.30(15)
C7 C8 C9 C10 -2.0(3)
C7 C8 C9 C19 179.94(16)
C8 C9 C10 C11 0.0(2)
C19 C9 C10 C11 178.07(17)
C8 C9 C10 C20 -178.29(17)
C19 C9 C10 C20 -0.2(3)
C9 C10 C11 C12 1.1(2)
C20 C10 C11 C12 179.44(16)
C10 C11 C12 C7 -0.3(2)
C10 C11 C12 N3 175.65(14)
C8 C7 C12 C11 -1.6(2)
N2 C7 C12 C11 179.49(14)
C8 C7 C12 N3 -177.19(14)
N2 C7 C12 N3 3.9(2)
C13 N3 C12 C11 138.35(17)
C13 N3 C12 C7 -45.9(2)
C12 N3 C13 O2 7.3(3)
C12 N3 C13 C14 -172.16(14)
O2 C13 C14 C15 36.5(2)
N3 C13 C14 C15 -144.00(16)
O2 C13 C14 C18 -139.76(18)
N3 C13 C14 C18 39.7(2)
C18 C14 C15 C16 -1.6(3)
C13 C14 C15 C16 -178.07(17)
C14 C15 C16 C17 1.9(3)
C18 N4 C17 C16 -2.8(3)
C15 C16 C17 N4 0.3(3)
C17 N4 C18 C14 3.1(3)
C15 C14 C18 N4 -1.0(3)
C13 C14 C18 N4 175.37(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21123305
2 PubChem 139073189
