Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 4-[(prop-2-en-1-yloxy)methyl]-3,6-bis(pyridin-2-yl)pyridazine
Filali, Mouad; Sebbar, Nada Kheira; Hökelek, Tuncer; Mague, Joel T.; Chakroune, Said; Ben-Tama, Abdessalam; El Hadrami, El Mestafa; Acta Crystallographica Section E 75 (2019) 1321–1326; doi:10.1107/S2056989019011186

data_2243059
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis and interaction energy and
 DFT studies of
 4-[(prop-2-en-1-yloxy)methyl]-3,6-bis(pyridin-2-yl)pyridazine
;
_journal_coeditor_code           LH5915
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1321
_journal_page_last               1326
_journal_paper_doi               10.1107/S2056989019011186
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C18 H16 N4 O'
_chemical_formula_moiety         'C18 H16 N4 O'
_chemical_formula_sum            'C18 H16 N4 O'
_chemical_formula_weight         304.35
_chemical_name_systematic
;
4-[(Prop-2-en-1-yloxy)methyl]-3,6-bis(pyridin-2-yl)pyridazine
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                90
_cell_angle_beta                 100.1320(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9420(2)
_cell_length_b                   15.1130(3)
_cell_length_c                   11.5829(3)
_cell_measurement_reflns_used    9267
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      74.4815
_cell_measurement_theta_min      4.8585
_cell_volume                     1540.91(6)
_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> (Sheldrick, 2008)
;
_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 0.987
_diffrn_measured_fraction_theta_max 0.967
_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  0.0287
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11678
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         74.473
_diffrn_reflns_theta_min         4.858
_diffrn_source                   'INCOATEC I\mS micro-focus source'
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.86
_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    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.241
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.150
_refine_ls_extinction_coef       0.0046(5)
_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   1.041
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3051
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0534P)^2^+0.3637P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1012
_reflns_number_gt                2688
_reflns_number_total             3051
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lh5915sup1.cif
_cod_data_source_block           I
_cod_database_code               2243059
_cod_database_fobs_code          2243059
_shelx_estimated_absorpt_t_min   0.841
_shelx_estimated_absorpt_t_max   0.949
_shelx_hkl_checksum              91509
_shelx_res_checksum              50229