Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of methyl 4-[3,6-bis(pyridin-2-yl)pyridazin-4-yl]benzoate
Filali, Mouad; El Ghayati, Lhoussaine; Hökelek, Tuncer; Mague, Joel T.; Ben-Tama, Abdessalam; El Hadrami, El Mestafa; Sebbar, Nada Kheira; Acta Crystallographica Section E 75 (2019) 1672–1678; doi:10.1107/S2056989019013732

data_2243149
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis and interaction energy and
 DFT studies of methyl 4-[3,6-bis(pyridin-2-yl)pyridazin-4-yl]benzoate
;
_journal_coeditor_code           LH5927
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1672
_journal_page_last               1678
_journal_paper_doi               10.1107/S2056989019013732
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C22 H16 N4 O2'
_chemical_formula_moiety         'C22 H16 N4 O2'
_chemical_formula_sum            'C22 H16 N4 O2'
_chemical_formula_weight         368.39
_chemical_name_systematic
;
Methyl 4-[3,6-bis(pyridin-2-yl)pyridazin-4-yl]benzoate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     'dual space'
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                95.7350(10)
_cell_angle_beta                 95.8130(10)
_cell_angle_gamma                101.7800(10)
_cell_formula_units_Z            2
_cell_length_a                   6.04640(10)
_cell_length_b                   11.7175(3)
_cell_length_c                   13.2931(3)
_cell_measurement_reflns_used    6104
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      74.6533
_cell_measurement_theta_min      3.3678
_cell_volume                     910.16(3)
_computing_cell_refinement
;
<i>SAINT</i> (Bruker, 2016)
;
_computing_data_collection
;
<i>APEX3</i> (Bruker, 2016)
;
_computing_data_reduction
;
<i>SAINT</i>  (Bruker, 2016)
;
_computing_molecular_graphics
;
<i>DIAMOND</i> (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
<i>SHELXTL</i> (Bruker, 2016)
;
_computing_structure_refinement
;
<i>SHELXL2018</i> (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7056
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         74.646
_diffrn_reflns_theta_min         3.368
_diffrn_source                   'INCOATEC I\mS micro-focus source'
_exptl_absorpt_coefficient_mu    0.723
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Krause <i>et al.</i>, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.165
_refine_ls_extinction_coef       0.0087(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
<i>SHELXL2018</i> (Sheldrick, 2015<i>b</i>)
;
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         3426
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0539P)^2^+0.2048P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.0982
_reflns_number_gt                3139
_reflns_number_total             3426
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lh5927sup1.cif
_cod_data_source_block           I
_cod_database_code               2243149
_cod_database_fobs_code          2243149
_shelx_estimated_absorpt_t_min   0.834
_shelx_estimated_absorpt_t_max   0.953
_shelx_hkl_checksum              82806
_shelx_res_checksum              38870