#------------------------------------------------------------------------------
#$Date: 2019-08-23 07:15:17 +0300 (Fri, 23 Aug 2019) $
#$Revision: 217671 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/30/2243059.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_2243059
loop_
_publ_author_name
'Filali, Mouad'
'Sebbar, Nada Kheira'
'Hökelek, Tuncer'
'Mague, Joel T.'
'Chakroune, Said'
'Ben-Tama, Abdessalam'
'El Hadrami, El Mestafa'
_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
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT  (Bruker, 2016)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_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       'ω 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
;
(SADABS; Krause et al., 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+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015b)
;
_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/[σ²(Fo²)+(0.0534P)²+0.3637P] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_cod_data_source_file            lh5915sup1.cif
_cod_data_source_block           I
_cod_database_code               2243059
_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.
;
_shelx_estimated_absorpt_t_min   0.841
_shelx_estimated_absorpt_t_max   0.949
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
O O1 0.27225(10) 0.47749(5) 0.30640(7) 0.0319(2) Uani d 1
N N1 0.19512(11) 0.50876(6) 0.70191(8) 0.0283(2) Uani d 1
N N2 0.27872(11) 0.58215(6) 0.70850(8) 0.0283(2) Uani d 1
N N3 0.49183(11) 0.71463(6) 0.53716(8) 0.0299(2) Uani d 1
N N4 0.07708(13) 0.31558(7) 0.53457(10) 0.0370(3) Uani d 1
C C1 0.17076(12) 0.45900(7) 0.60429(10) 0.0249(2) Uani d 1
C C2 0.23110(12) 0.48225(7) 0.50338(10) 0.0244(2) Uani d 1
C C3 0.31696(12) 0.55846(7) 0.51158(10) 0.0257(2) Uani d 1
H H3 0.3616(15) 0.5785(9) 0.4416(12) 0.030(3) Uiso d 1
C C4 0.33924(12) 0.60672(7) 0.61566(9) 0.0244(2) Uani d 1
C C5 0.43278(12) 0.68871(7) 0.63070(10) 0.0250(2) Uani d 1
C C6 0.45861(13) 0.73441(8) 0.73683(10) 0.0292(3) Uani d 1
H H6 0.4125(17) 0.7131(10) 0.8002(13) 0.040(4) Uiso d 1
C C7 0.54897(14) 0.80913(8) 0.74716(11) 0.0329(3) Uani d 1
H H7 0.5668(18) 0.8438(11) 0.8229(15) 0.049(4) Uiso d 1
C C8 0.61156(14) 0.83614(8) 0.65191(11) 0.0326(3) Uani d 1
H H8 0.6740(17) 0.8887(10) 0.6564(14) 0.042(4) Uiso d 1
C C9 0.57918(14) 0.78700(8) 0.54977(11) 0.0323(3) Uani d 1
H H9 0.6207(17) 0.8041(10) 0.4814(14) 0.043(4) Uiso d 1
C C10 0.07702(12) 0.37891(7) 0.61505(10) 0.0269(3) Uani d 1
C C11 -0.00417(14) 0.37100(9) 0.70670(11) 0.0346(3) Uani d 1
H H11 -0.0048(18) 0.4190(11) 0.7619(14) 0.044(4) Uiso d 1
C C12 -0.08744(15) 0.29497(9) 0.71477(12) 0.0404(3) Uani d 1
H H12 -0.147(2) 0.2897(11) 0.7774(16) 0.058(5) Uiso d 1
C C13 -0.08794(16) 0.22904(9) 0.63254(12) 0.0405(3) Uani d 1
H H13 -0.1415(19) 0.1766(12) 0.6368(14) 0.050(4) Uiso d 1
C C14 -0.00414(18) 0.24243(9) 0.54512(13) 0.0440(3) Uani d 1
H H14 -0.0035(19) 0.1969(11) 0.4852(15) 0.052(5) Uiso d 1
C C15 0.20351(13) 0.43087(8) 0.39007(10) 0.0279(3) Uani d 1
H H15A 0.0898(16) 0.4252(9) 0.3600(12) 0.032(3) Uiso d 1
H H15B 0.2466(16) 0.3702(10) 0.4016(12) 0.036(4) Uiso d 1
C C16 0.23624(15) 0.43750(8) 0.19364(10) 0.0321(3) Uani d 1
H H16A 0.1233(17) 0.4420(9) 0.1637(13) 0.037(4) Uiso d 1
H H16B 0.2670(16) 0.3739(10) 0.1992(13) 0.038(4) Uiso d 1
C C17 0.32018(17) 0.48569(9) 0.11329(11) 0.0377(3) Uani d 1
H H17 0.436(2) 0.4884(12) 0.1409(17) 0.065(5) Uiso d 1
C C18 0.2574(2) 0.51972(11) 0.01194(13) 0.0497(4) Uani d 1
H H18A 0.150(2) 0.5087(12) -0.0128(17) 0.065(6) Uiso d 1
H H18B 0.314(2) 0.5515(13) -0.0442(18) 0.068(5) 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
C15 O1 C16 111.09(9)
N2 N1 C1 121.37(9)
N1 N2 C4 119.14(9)
C9 N3 C5 117.07(10)
C10 N4 C14 117.42(11)
N1 C1 C2 121.82(10)
N1 C1 C10 113.24(10)
C2 C1 C10 124.93(10)
C3 C2 C1 116.06(10)
C3 C2 C15 119.63(10)
C1 C2 C15 124.29(10)
C2 C3 C4 119.36(10)
C2 C3 H3 119.3(8)
C4 C3 H3 121.3(8)
N2 C4 C3 122.25(10)
N2 C4 C5 115.80(10)
C3 C4 C5 121.95(10)
N3 C5 C6 122.61(10)
N3 C5 C4 116.15(10)
C6 C5 C4 121.24(10)
C7 C6 C5 119.03(11)
C7 C6 H6 122.1(9)
C5 C6 H6 118.8(9)
C6 C7 C8 118.99(11)
C6 C7 H7 120.0(9)
C8 C7 H7 121.0(9)
C9 C8 C7 118.05(11)
C9 C8 H8 121.2(9)
C7 C8 H8 120.7(9)
N3 C9 C8 124.25(11)
N3 C9 H9 115.5(9)
C8 C9 H9 120.3(9)
N4 C10 C11 122.32(11)
N4 C10 C1 117.02(10)
C11 C10 C1 120.65(10)
C12 C11 C10 118.85(12)
C12 C11 H11 120.9(9)
C10 C11 H11 120.3(10)
C13 C12 C11 119.41(12)
C13 C12 H12 121.3(10)
C11 C12 H12 119.3(10)
C14 C13 C12 117.79(12)
C14 C13 H13 121.0(10)
C12 C13 H13 121.2(10)
N4 C14 C13 124.22(13)
N4 C14 H14 116.4(10)
C13 C14 H14 119.4(10)
O1 C15 C2 108.29(9)
O1 C15 H15A 109.5(8)
C2 C15 H15A 110.0(8)
O1 C15 H15B 110.2(8)
C2 C15 H15B 111.0(8)
H15A C15 H15B 107.9(11)
O1 C16 C17 108.01(10)
O1 C16 H16A 109.7(8)
C17 C16 H16A 109.7(8)
O1 C16 H16B 109.5(9)
C17 C16 H16B 110.4(8)
H16A C16 H16B 109.5(12)
C18 C17 C16 124.63(15)
C18 C17 H17 120.8(11)
C16 C17 H17 114.5(11)
C17 C18 H18A 116.3(12)
C17 C18 H18B 125.0(12)
H18A C18 H18B 118.4(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C15 1.4224(13)
O1 C16 1.4237(14)
N1 N2 1.3322(13)
N1 C1 1.3434(15)
N2 C4 1.3386(14)
N3 C9 1.3370(15)
N3 C5 1.3445(14)
N4 C10 1.3362(15)
N4 C14 1.3400(17)
C1 C2 1.4151(15)
C1 C10 1.4901(15)
C2 C3 1.3782(15)
C2 C15 1.5075(15)
C3 C4 1.3930(15)
C3 H3 1.012(14)
C4 C5 1.4880(15)
C5 C6 1.3934(16)
C6 C7 1.3813(17)
C6 H6 0.959(15)
C7 C8 1.3836(17)
C7 H7 1.010(17)
C8 C9 1.3836(17)
C8 H8 0.966(16)
C9 H9 0.968(15)
C10 C11 1.3926(17)
C11 C12 1.3813(18)
C11 H11 0.968(17)
C12 C13 1.378(2)
C12 H12 0.974(17)
C13 C14 1.377(2)
C13 H13 0.931(18)
C14 H14 0.978(17)
C15 H15A 1.019(14)
C15 H15B 0.994(15)
C16 C17 1.4851(18)
C16 H16A 1.011(15)
C16 H16B 0.999(15)
C17 C18 1.314(2)
C17 H17 1.03(2)
C18 H18A 0.96(2)
C18 H18B 1.01(2)
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C11 3.2992(16) 3_566 yes
O1 H3 2.232(14) . yes
O1 H11 2.850(16) 3_566 yes
N1 C8 3.4105(15) 2_646 yes
N4 C15 2.7895(16) . yes
N1 H8 2.586(15) 2_646 yes
N1 H11 2.441(16) . yes
N1 H15A 2.713(14) 3_566 yes
N2 H18B 2.86(2) 1_556 yes
N2 H13 2.744(17) 2_556 yes
N2 H6 2.455(15) . yes
N3 H3 2.522(14) . yes
N3 H15B 2.652(15) 3_666 yes
N4 H15A 2.632(14) . yes
N4 H15B 2.485(14) . yes
C1 C7 3.5853(17) 2_646 yes
C2 C10 3.5420(15) 3_566 yes
C3 C11 3.5866(17) 3_566 yes
C6 C12 3.5808(18) 2_556 yes
C8 C10 3.5797(17) 2_656 yes
C11 C15 3.5633(18) 3_566 yes
C1 H7 2.925(17) 2_646 yes
C6 H16B 2.933(15) 3_666 yes
C9 H15B 2.842(15) 3_666 yes
C18 H8 2.920(16) 2_645 yes
H6 H9 2.56(2) 4_576 yes
H8 N1 2.586(16) 2_656 yes
H11 H16A 2.57(2) 3_566 yes
H12 C6 2.886(18) 2_546 yes
H12 H14 2.53(3) 4_566 yes
H13 H18B 2.55(3) 2_545 yes
H15A H16A 2.36(2) . yes
H15B H16B 2.38(2) . yes
H16A H18A 2.33(2) . yes
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
C8 H8 N1 2_656 0.966(16) 2.585(16) 3.4104(15) 143.4(12) yes
C15 H15B Cg 3_666 0.994(15) 2.990(15) 3.8760(13) 149.0(11) 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
C1 N1 N2 C4 0.15(16)
N2 N1 C1 C2 -0.61(16)
N2 N1 C1 C10 178.92(9)
N1 C1 C2 C3 0.42(15)
C10 C1 C2 C3 -179.06(10)
N1 C1 C2 C15 -177.88(10)
C10 C1 C2 C15 2.64(17)
C1 C2 C3 C4 0.20(15)
C15 C2 C3 C4 178.58(10)
N1 N2 C4 C3 0.49(16)
N1 N2 C4 C5 -179.18(9)
C2 C3 C4 N2 -0.66(16)
C2 C3 C4 C5 179.00(10)
C9 N3 C5 C6 0.51(17)
C9 N3 C5 C4 -178.47(10)
N2 C4 C5 N3 -178.91(10)
C3 C4 C5 N3 1.41(15)
N2 C4 C5 C6 2.09(15)
C3 C4 C5 C6 -177.59(10)
N3 C5 C6 C7 -0.32(18)
C4 C5 C6 C7 178.61(10)
C5 C6 C7 C8 -0.24(18)
C6 C7 C8 C9 0.57(18)
C5 N3 C9 C8 -0.14(18)
C7 C8 C9 N3 -0.4(2)
C14 N4 C10 C11 -0.41(18)
C14 N4 C10 C1 178.51(11)
N1 C1 C10 N4 -164.56(10)
C2 C1 C10 N4 14.96(16)
N1 C1 C10 C11 14.38(15)
C2 C1 C10 C11 -166.10(11)
N4 C10 C11 C12 0.07(19)
C1 C10 C11 C12 -178.81(11)
C10 C11 C12 C13 0.1(2)
C11 C12 C13 C14 0.0(2)
C10 N4 C14 C13 0.6(2)
C12 C13 C14 N4 -0.4(2)
C16 O1 C15 C2 -173.64(9)
C3 C2 C15 O1 -2.59(14)
C1 C2 C15 O1 175.66(9)
C15 O1 C16 C17 -176.11(10)
O1 C16 C17 C18 -126.92(14)

_cod_database_fobs_code 2243059
