#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/61/2226135.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_2226135
loop_
_publ_author_name
'Ather, Abdul Qayyum'
'Şahin, Onur'
'Khan, Islam Ullah'
'Khan, Misbahul Ain'
'Büyükgüngör, Orhan'
_publ_section_title
;
 3-(Piperidin-1-yl)-6-(1H-pyrazol-1-yl)pyridazine
;
_journal_coeditor_code           HB5436
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1295
_journal_paper_doi               10.1107/S1600536810016491
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H15 N5'
_chemical_formula_moiety         'C12 H15 N5'
_chemical_formula_sum            'C12 H15 N5'
_chemical_formula_weight         229.29
_chemical_name_systematic
;
3-(Piperidin-1-yl)-6-(1H-pyrazol-1-yl)pyridazine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 103.230(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9665(6)
_cell_length_b                   20.189(3)
_cell_length_c                   9.9695(13)
_cell_measurement_reflns_used    1639
_cell_measurement_temperature    296
_cell_measurement_theta_max      21.27
_cell_measurement_theta_min      2.33
_cell_volume                     1169.0(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_sigmaI/netI    0.0708
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11710
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1405
_refine_ls_R_factor_gt           0.0580
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0863P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1437
_refine_ls_wR_factor_ref         0.1815
_reflns_number_gt                1282
_reflns_number_total             2674
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5436.cif
_cod_data_source_block           I
_cod_original_cell_volume        1169.0(2)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2226135
_cod_database_fobs_code          2226135
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3406(6) 0.72572(15) 0.3173(3) 0.0738(9) Uani d . 1 . .
H H1 0.4014 0.6901 0.2782 0.089 Uiso calc R 1 . .
C C2 0.1112(6) 0.74333(16) 0.2984(3) 0.0756(9) Uani d . 1 . .
H H2 -0.0087 0.7203 0.2415 0.091 Uiso calc R 1 . .
C C3 0.4568(5) 0.77160(14) 0.4052(3) 0.0639(8) Uani d . 1 . .
H H3 0.6155 0.7740 0.4384 0.077 Uiso calc R 1 . .
C C4 0.3331(4) 0.86969(12) 0.5224(2) 0.0452(6) Uani d . 1 . .
C C5 0.1481(4) 0.90081(13) 0.5592(3) 0.0501(7) Uani d . 1 . .
H H5 -0.0019 0.8857 0.5274 0.060 Uiso calc R 1 . .
C C6 0.1955(4) 0.95375(14) 0.6429(2) 0.0496(7) Uani d . 1 . .
H H6 0.0779 0.9767 0.6699 0.060 Uiso calc R 1 . .
C C7 0.4275(4) 0.97398(12) 0.6893(2) 0.0415(6) Uani d . 1 . .
C C8 0.3360(4) 1.08147(13) 0.7801(3) 0.0540(7) Uani d . 1 . .
H H8A 0.1774 1.0665 0.7559 0.065 Uiso calc R 1 . .
H H8B 0.3581 1.1125 0.7098 0.065 Uiso calc R 1 . .
C C9 0.3800(4) 1.11603(15) 0.9163(3) 0.0638(8) Uani d . 1 . .
H H9A 0.3378 1.0870 0.9840 0.077 Uiso calc R 1 . .
H H9B 0.2842 1.1553 0.9085 0.077 Uiso calc R 1 . .
C C10 0.6306(4) 1.13584(14) 0.9652(3) 0.0674(8) Uani d . 1 . .
H H10A 0.6698 1.1689 0.9037 0.081 Uiso calc R 1 . .
H H10B 0.6567 1.1548 1.0569 0.081 Uiso calc R 1 . .
C C11 0.7792(4) 1.07512(14) 0.9672(3) 0.0580(8) Uani d . 1 . .
H H11A 0.9401 1.0879 0.9932 0.070 Uiso calc R 1 . .
H H11B 0.7501 1.0443 1.0359 0.070 Uiso calc R 1 . .
C C12 0.7328(4) 1.04124(14) 0.8292(3) 0.0530(7) Uani d . 1 . .
H H12A 0.7779 1.0702 0.7623 0.064 Uiso calc R 1 . .
H H12B 0.8244 1.0012 0.8360 0.064 Uiso calc R 1 . .
N N1 0.0810(4) 0.79630(13) 0.3697(2) 0.0692(7) Uani d . 1 . .
N N2 0.2982(4) 0.81341(11) 0.4357(2) 0.0536(6) Uani d . 1 . .
N N3 0.5964(3) 0.94188(11) 0.6493(2) 0.0493(6) Uani d . 1 . .
N N4 0.5475(3) 0.88877(11) 0.5649(2) 0.0523(6) Uani d . 1 . .
N N5 0.4896(3) 1.02450(10) 0.7825(2) 0.0449(5) Uani 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 0.0033 0.0016 '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 0.0061 0.0033 '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
C3 C1 C2 . . 104.9(3) ?
C3 C1 H1 . . 127.6 ?
C2 C1 H1 . . 127.6 ?
N1 C2 C1 . . 112.8(3) ?
N1 C2 H2 . . 123.6 ?
C1 C2 H2 . . 123.6 ?
C1 C3 N2 . . 106.9(3) ?
C1 C3 H3 . . 126.5 ?
N2 C3 H3 . . 126.5 ?
N4 C4 C5 . . 123.9(2) ?
N4 C4 N2 . . 115.5(2) n
C5 C4 N2 . . 120.7(2) ?
C6 C5 C4 . . 117.1(2) ?
C6 C5 H5 . . 121.5 ?
C4 C5 H5 . . 121.5 ?
C5 C6 C7 . . 118.9(2) ?
C5 C6 H6 . . 120.6 ?
C7 C6 H6 . . 120.6 ?
N3 C7 N5 . . 117.3(2) ?
N3 C7 C6 . . 120.8(2) ?
N5 C7 C6 . . 121.9(2) ?
N5 C8 C9 . . 111.8(2) ?
N5 C8 H8A . . 109.3 ?
C9 C8 H8A . . 109.3 ?
N5 C8 H8B . . 109.3 ?
C9 C8 H8B . . 109.3 ?
H8A C8 H8B . . 107.9 ?
C8 C9 C10 . . 111.7(2) ?
C8 C9 H9A . . 109.3 ?
C10 C9 H9A . . 109.3 ?
C8 C9 H9B . . 109.3 ?
C10 C9 H9B . . 109.3 ?
H9A C9 H9B . . 107.9 ?
C11 C10 C9 . . 108.8(2) ?
C11 C10 H10A . . 109.9 ?
C9 C10 H10A . . 109.9 ?
C11 C10 H10B . . 109.9 ?
C9 C10 H10B . . 109.9 ?
H10A C10 H10B . . 108.3 ?
C12 C11 C10 . . 111.9(2) ?
C12 C11 H11A . . 109.2 ?
C10 C11 H11A . . 109.2 ?
C12 C11 H11B . . 109.2 ?
C10 C11 H11B . . 109.2 ?
H11A C11 H11B . . 107.9 ?
N5 C12 C11 . . 111.04(19) ?
N5 C12 H12A . . 109.4 ?
C11 C12 H12A . . 109.4 ?
N5 C12 H12B . . 109.4 ?
C11 C12 H12B . . 109.4 ?
H12A C12 H12B . . 108.0 ?
C2 N1 N2 . . 103.6(2) ?
C3 N2 N1 . . 111.8(2) ?
C3 N2 C4 . . 128.7(2) ?
N1 N2 C4 . . 119.4(2) n
C7 N3 N4 . . 120.05(19) ?
C4 N4 N3 . . 119.34(19) ?
C7 N5 C12 . . 118.89(18) ?
C7 N5 C8 . . 120.04(18) ?
C12 N5 C8 . . 113.3(2) ?
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
C1 C3 . 1.352(4) ?
C1 C2 . 1.384(4) ?
C1 H1 . 0.9300 ?
C2 N1 . 1.319(4) n
C2 H2 . 0.9300 ?
C3 N2 . 1.353(3) n
C3 H3 . 0.9300 ?
C4 N4 . 1.310(3) n
C4 C5 . 1.391(3) ?
C4 N2 . 1.414(3) n
C5 C6 . 1.346(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.415(3) ?
C6 H6 . 0.9300 ?
C7 N3 . 1.334(3) n
C7 N5 . 1.372(3) n
C8 N5 . 1.467(3) ?
C8 C9 . 1.496(4) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.516(3) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.510(4) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.504(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 N5 . 1.458(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
N1 N2 . 1.357(3) n
N3 N4 . 1.353(3) n
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
C3 C1 C2 N1 . . . . -0.5(4) ?
C2 C1 C3 N2 . . . . 0.4(3) ?
N4 C4 C5 C6 . . . . 0.4(4) ?
N2 C4 C5 C6 . . . . 179.5(2) ?
C4 C5 C6 C7 . . . . -0.7(4) ?
C5 C6 C7 N3 . . . . 1.0(4) ?
C5 C6 C7 N5 . . . . -175.2(2) ?
N5 C8 C9 C10 . . . . 54.4(3) ?
C8 C9 C10 C11 . . . . -54.9(3) ?
C9 C10 C11 C12 . . . . 55.6(3) ?
C10 C11 C12 N5 . . . . -55.7(3) ?
C1 C2 N1 N2 . . . . 0.4(3) ?
C1 C3 N2 N1 . . . . -0.2(3) ?
C1 C3 N2 C4 . . . . -179.6(2) ?
C2 N1 N2 C3 . . . . -0.1(3) ?
C2 N1 N2 C4 . . . . 179.4(2) ?
N4 C4 N2 C3 . . . . 9.6(4) ?
C5 C4 N2 C3 . . . . -169.6(2) ?
N4 C4 N2 N1 . . . . -169.8(2) ?
C5 C4 N2 N1 . . . . 11.0(3) ?
N5 C7 N3 N4 . . . . 175.5(2) ?
C6 C7 N3 N4 . . . . -0.9(3) ?
C5 C4 N4 N3 . . . . -0.3(4) ?
N2 C4 N4 N3 . . . . -179.4(2) ?
C7 N3 N4 C4 . . . . 0.5(3) ?
N3 C7 N5 C12 . . . . 1.6(3) ?
C6 C7 N5 C12 . . . . 177.9(2) ?
N3 C7 N5 C8 . . . . 148.8(2) ?
C6 C7 N5 C8 . . . . -34.8(3) ?
C11 C12 N5 C7 . . . . -156.3(2) ?
C11 C12 N5 C8 . . . . 54.3(3) ?
C9 C8 N5 C7 . . . . 157.0(2) ?
C9 C8 N5 C12 . . . . -54.1(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745035
