#------------------------------------------------------------------------------
#$Date: 2024-10-31 04:58:08 +0200 (Thu, 31 Oct 2024) $
#$Revision: 295686 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/26/2312671.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_2312671
loop_
_publ_author_name
'Wzgarda-Raj, Kinga'
'Dominikowska, Justyna'
'Wojtulewski, Sławomir'
'Rybarczyk-Pirek, Agnieszka J'
_publ_section_title
;
 X-ray studies of three 3,6-bis(pyridin-2-yl)-1,2,4,5-tetrazine
 cocrystals: an unexpected molecular conformation stabilized by hydrogen
 bonds.
;
_journal_coeditor_code           DG3037
_journal_issue                   'Pt 2'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              52
_journal_page_last               60
_journal_paper_doi               10.1107/S2053229622012256
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C12 H8 N6, 2C6 H5 N O3'
_chemical_formula_moiety         'C12 H8 N6, 2(C6 H5 N O3)'
_chemical_formula_sum            'C24 H18 N8 O6'
_chemical_formula_weight         514.46
_chemical_name_systematic
;
3,6-Bis(pyridin-2-yl)-1,2,4,5-tetrazine--4-carboxypyridine N-oxide (1/2)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.835(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.8067(2)
_cell_length_b                   21.3885(7)
_cell_length_c                   14.2669(6)
_cell_measurement_reflns_used    4366
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.1940
_cell_measurement_theta_min      3.8630
_cell_volume                     1105.78(9)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
olex2.solve (Bourhis et al.,  2015)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4052
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
;
Rigaku OD SuperNova (Dual, Cu at home/near) diffractometer with an Atlas
detector
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10838
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.488
_diffrn_reflns_theta_min         3.855
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.973
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_description       plate
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.037
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.296
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0421
_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)+(0.0682P)²+0.2944P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1110
_reflns_number_gt                1806
_reflns_number_total             2048
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dg3037sup1.cif
_cod_data_source_block           II
_cod_database_code               2312671
_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+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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O11 0.0482(3) 0.36504(5) 0.88197(8) 0.0185(3) Uani d 1 . .
O O141 -0.1328(3) 0.28463(5) 0.44542(8) 0.0179(3) Uani d 1 . .
O O142 0.1565(3) 0.20133(5) 0.53135(8) 0.0199(3) Uani d 1 . .
N N11 0.0458(3) 0.33948(6) 0.79700(9) 0.0132(3) Uani d 1 . .
N N1 1.1510(3) 0.44888(6) 0.47045(10) 0.0159(3) Uani d 1 . .
N N2 0.7372(4) 0.53549(6) 0.43554(10) 0.0159(3) Uani d 1 . .
N N32 0.5662(3) 0.51014(6) 0.24112(10) 0.0162(3) Uani d 1 . .
C C13 -0.1522(4) 0.34222(7) 0.62322(11) 0.0131(3) Uani d 1 . .
H H13 -0.279926 0.362247 0.564875 0.016 Uiso calc 1 . .
C C12 -0.1422(4) 0.36841(7) 0.71227(11) 0.0136(3) Uani d 1 . .
H H12 -0.264466 0.405830 0.714041 0.016 Uiso calc 1 . .
C C141 0.0080(4) 0.25757(7) 0.52272(11) 0.0135(3) Uani d 1 . .
C C15 0.2192(4) 0.25747(7) 0.70881(11) 0.0137(3) Uani d 1 . .
H H15 0.341600 0.219858 0.708654 0.016 Uiso calc 1 . .
C C16 0.2274(4) 0.28480(7) 0.79662(11) 0.0139(3) Uani d 1 . .
H H16 0.357243 0.265892 0.855793 0.017 Uiso calc 1 . .
C C14 0.0281(4) 0.28593(7) 0.62008(11) 0.0123(3) Uani d 1 . .
C C3 0.8910(4) 0.48456(7) 0.40830(11) 0.0135(3) Uani d 1 . .
C C35 0.7397(4) 0.39601(7) 0.17179(12) 0.0179(3) Uani d 1 . .
H H35 0.797713 0.358080 0.148287 0.021 Uiso calc 1 . .
C C34 0.5300(4) 0.44019(8) 0.10720(12) 0.0184(3) Uani d 1 . .
H H34 0.444011 0.432303 0.039907 0.022 Uiso calc 1 . .
C C33 0.4516(4) 0.49631(7) 0.14517(11) 0.0171(3) Uani d 1 . .
H H33 0.311986 0.525837 0.101626 0.021 Uiso calc 1 . .
C C36 0.8615(4) 0.40915(7) 0.27179(12) 0.0166(3) Uani d 1 . .
H H36 1.000670 0.380298 0.316770 0.020 Uiso calc 1 . .
C C31 0.7687(4) 0.46704(7) 0.30281(11) 0.0137(3) Uani d 1 . .
H H142 0.098(7) 0.1794(12) 0.4615(19) 0.042(7) Uiso d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C141 O142 H142 . . 110.8(13) ?
O11 N11 C12 . . 118.81(13) ?
O11 N11 C16 . . 119.79(12) ?
C12 N11 C16 . . 121.40(13) ?
N2 N1 C3 3_766 . 117.99(13) ?
N1 N2 C3 3_766 . 117.63(13) ?
C33 N32 C31 . . 117.46(13) ?
C12 C13 H13 . . 119.8 ?
C12 C13 C14 . . 120.40(13) ?
C14 C13 H13 . . 119.8 ?
N11 C12 C13 . . 119.73(14) ?
N11 C12 H12 . . 120.1 ?
C13 C12 H12 . . 120.1 ?
O141 C141 O142 . . 125.21(14) ?
O141 C141 C14 . . 122.18(14) ?
O142 C141 C14 . . 112.61(13) ?
C16 C15 H15 . . 119.9 ?
C16 C15 C14 . . 120.17(14) ?
C14 C15 H15 . . 119.9 ?
N11 C16 C15 . . 120.00(13) ?
N11 C16 H16 . . 120.0 ?
C15 C16 H16 . . 120.0 ?
C13 C14 C141 . . 119.64(13) ?
C15 C14 C13 . . 118.30(13) ?
C15 C14 C141 . . 122.06(13) ?
N1 C3 N2 . . 124.38(14) ?
N1 C3 C31 . . 117.72(14) ?
N2 C3 C31 . . 117.90(13) ?
C34 C35 H35 . . 120.4 ?
C36 C35 H35 . . 120.4 ?
C36 C35 C34 . . 119.20(14) ?
C35 C34 H34 . . 120.7 ?
C33 C34 C35 . . 118.59(15) ?
C33 C34 H34 . . 120.7 ?
N32 C33 C34 . . 123.37(14) ?
N32 C33 H33 . . 118.3 ?
C34 C33 H33 . . 118.3 ?
C35 C36 H36 . . 121.0 ?
C35 C36 C31 . . 117.92(14) ?
C31 C36 H36 . . 121.0 ?
N32 C31 C3 . . 115.54(13) ?
N32 C31 C36 . . 123.46(14) ?
C36 C31 C3 . . 121.00(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O11 N11 . 1.3273(16) ?
O141 C141 . 1.2150(19) ?
O142 C141 . 1.3187(19) ?
O142 H142 . 1.06(3) ?
N11 C12 . 1.3515(19) ?
N11 C16 . 1.359(2) ?
N1 N2 3_766 1.3200(18) ?
N1 C3 . 1.3454(19) ?
N2 C3 . 1.349(2) ?
N32 C33 . 1.336(2) ?
N32 C31 . 1.343(2) ?
C13 H13 . 0.9300 ?
C13 C12 . 1.378(2) ?
C13 C14 . 1.393(2) ?
C12 H12 . 0.9300 ?
C141 C14 . 1.496(2) ?
C15 H15 . 0.9300 ?
C15 C16 . 1.374(2) ?
C15 C14 . 1.392(2) ?
C16 H16 . 0.9300 ?
C3 C31 . 1.481(2) ?
C35 H35 . 0.9300 ?
C35 C34 . 1.389(2) ?
C35 C36 . 1.387(2) ?
C34 H34 . 0.9300 ?
C34 C33 . 1.386(2) ?
C33 H33 . 0.9300 ?
C36 H36 . 0.9300 ?
C36 C31 . 1.396(2) ?
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
_geom_hbond_publ_flag
C12 H12 N2 3_566 0.93 2.65 3.2978(19) 127.4 yes
C12 H12 N32 3_566 0.93 2.33 3.2329(19) 165.0 yes
O142 H142 O11 4_565 1.06(3) 1.45(3) 2.4878(15) 165(2) yes
O142 H142 N11 4_565 1.06(3) 2.33(3) 3.3549(17) 162(2) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O11 N11 C12 C13 . . . . -179.15(12) ?
O11 N11 C16 C15 . . . . 178.60(13) ?
O141 C141 C14 C13 . . . . 6.8(2) ?
O141 C141 C14 C15 . . . . -173.91(13) ?
O142 C141 C14 C13 . . . . -172.98(13) ?
O142 C141 C14 C15 . . . . 6.3(2) ?
N1 N2 C3 N1 3_766 . . . -0.2(2) ?
N1 N2 C3 C31 3_766 . . . -179.57(12) ?
N1 C3 C31 N32 . . . . -167.38(13) ?
N1 C3 C31 C36 . . . . 12.7(2) ?
N2 N1 C3 N2 3_766 . . . 0.2(2) ?
N2 N1 C3 C31 3_766 . . . 179.58(12) ?
N2 C3 C31 N32 . . . . 12.00(19) ?
N2 C3 C31 C36 . . . . -167.89(14) ?
C12 N11 C16 C15 . . . . -0.6(2) ?
C12 C13 C14 C141 . . . . 178.80(13) ?
C12 C13 C14 C15 . . . . -0.5(2) ?
C16 N11 C12 C13 . . . . 0.1(2) ?
C16 C15 C14 C13 . . . . 0.0(2) ?
C16 C15 C14 C141 . . . . -179.32(13) ?
C14 C13 C12 N11 . . . . 0.5(2) ?
C14 C15 C16 N11 . . . . 0.6(2) ?
C35 C34 C33 N32 . . . . -0.3(2) ?
C35 C36 C31 N32 . . . . 0.5(2) ?
C35 C36 C31 C3 . . . . -179.58(13) ?
C34 C35 C36 C31 . . . . -0.5(2) ?
C33 N32 C31 C3 . . . . 179.71(12) ?
C33 N32 C31 C36 . . . . -0.4(2) ?
C36 C35 C34 C33 . . . . 0.4(2) ?
C31 N32 C33 C34 . . . . 0.3(2) ?

_cod_database_fobs_code 2312671
