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.
Wzgarda-Raj, Kinga; Dominikowska, Justyna; Wojtulewski, Sławomir; Rybarczyk-Pirek, Agnieszka J; Acta crystallographica. Section C, Structural chemistry 79 (2023) 52–60; doi:10.1107/S2053229622012256

data_2312670
_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 H3 Br3 O'
_chemical_formula_moiety         'C12 H8 N6, 2(C6 H3 Br3 O)'
_chemical_formula_sum            'C24 H14 Br6 N6 O2'
_chemical_formula_weight         897.81
_chemical_name_systematic
;
3,6-Bis(pyridin-2-yl)-1,2,4,5-tetrazine--2,4,6-tribromophenol (1/2)
;
_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
_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                93.420(4)
_cell_angle_beta                 94.065(4)
_cell_angle_gamma                90.317(4)
_cell_formula_units_Z            1
_cell_length_a                   4.6374(2)
_cell_length_b                   11.0096(6)
_cell_length_c                   13.0262(7)
_cell_measurement_reflns_used    4275
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.3840
_cell_measurement_theta_min      3.4110
_cell_volume                     662.18(6)
_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 <i>et al.</i>,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
olex2.solve (Bourhis <i>et al.</i>,  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       '\w 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  0.0352
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7368
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.479
_diffrn_reflns_theta_min         3.408
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    11.268
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    2.252
_exptl_crystal_description       plate
_exptl_crystal_F_000             426
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.039
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.852
_refine_ls_extinction_coef       0.00063(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015<i>b</i>)
;
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0295
_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/[\s^2^(Fo^2^)+(0.0549P)^2^+0.1998P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0803
_reflns_number_gt                2256
_reflns_number_total             2453
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            dg3037sup1.cif
_cod_data_source_block           I
_cod_database_code               2312670
_shelx_hkl_checksum              72375
_shelx_res_checksum              81422
_cod_database_fobs_code 2312670