#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/33/4023331.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4023331
loop_
_publ_author_name
'Kate M. Clapham'
'Andrei S. Batsanov'
'Ryan D. R. Greenwood'
'Martin R. Bryce'
'Amy E. Smith'
'Brian Tarbit'
_publ_contact_author             'Andrei S.Batsanov'
_publ_contact_author_email       a.s.batsanov@durham.ac.uk
_publ_section_title
;
 Functionalized Heteroarylpyridazines and Pyridazin-3(2H)-one
 Derivatives via Palladium-Catalyzed Cross-Coupling Methodology
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2176
_journal_page_last               2181
_journal_paper_doi               10.1021/jo702420q
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C15 H12 N4 O'
_chemical_formula_sum            'C15 H12 N4 O'
_chemical_formula_weight         264.29
_chemical_melting_point          439.2(3)
_chemical_name_systematic
' 3-methoxy-6-phenyl-4-(pyrimidin-5-yl)pyridazine   '
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                76.94(1)
_cell_angle_beta                 83.20(1)
_cell_angle_gamma                81.19(1)
_cell_formula_units_Z            2
_cell_length_a                   3.8868(4)
_cell_length_b                   10.5556(12)
_cell_length_c                   15.3809(17)
_cell_measurement_reflns_used    3559
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      2.65
_cell_volume                     605.16(11)
_computing_cell_refinement       'SAINT version 6.45A (Bruker, 2003)'
_computing_data_collection       'SMART version 5.049 (Bruker, 1998)'
_computing_data_reduction        'SAINT version 6.45A (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL version 6.14 (Bruker, 2003)'
_computing_publication_material  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_refinement  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_solution    'SHELXTL version 6.14 (Bruker, 2003)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Siemens SMART 1K CCD area detector'
_diffrn_measurement_method       'ω 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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7255
_diffrn_reflns_theta_full        28.99
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         1.36
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS 2.10 (Bruker, 2003), R(int)=0.043 before correction'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0405
_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)+(0.0582P)²+0.1264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1107
_reflns_number_gt                2505
_reflns_number_total             3174
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo702420q-File001_4.cif
_cod_data_source_block           22
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023331
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3793(2) 0.65227(8) 0.33088(6) 0.0203(2) Uani 1 1 d . . .
N1 N 0.0817(3) 0.34221(10) 0.37795(7) 0.0191(2) Uani 1 1 d . . .
N2 N 0.1831(3) 0.45380(10) 0.38858(7) 0.0193(2) Uani 1 1 d . . .
C3 C 0.2820(3) 0.54133(11) 0.31776(8) 0.0161(2) Uani 1 1 d . . .
C4 C 0.2969(3) 0.52485(11) 0.22830(8) 0.0152(2) Uani 1 1 d . . .
C5 C 0.1998(3) 0.40855(11) 0.21925(8) 0.0155(2) Uani 1 1 d . . .
H5 H 0.207(4) 0.3906(14) 0.1596(10) 0.018(3) Uiso 1 1 d . . .
C6 C 0.0873(3) 0.31845(11) 0.29638(8) 0.0154(2) Uani 1 1 d . . .
C7 C 0.3679(4) 0.66490(14) 0.42323(9) 0.0238(3) Uani 1 1 d . . .
H71 H 0.555(4) 0.6027(16) 0.4519(11) 0.034(4) Uiso 1 1 d . . .
H72 H 0.138(5) 0.6512(16) 0.4541(11) 0.034(4) Uiso 1 1 d . . .
H73 H 0.413(4) 0.7544(16) 0.4198(10) 0.027(4) Uiso 1 1 d . . .
N11 N 0.7090(3) 0.67864(10) 0.00322(7) 0.0207(2) Uani 1 1 d . . .
C12 C 0.6135(3) 0.80448(12) 0.00785(9) 0.0211(3) Uani 1 1 d . . .
H12 H 0.691(4) 0.8697(16) -0.0418(11) 0.029(4) Uiso 1 1 d . . .
N13 N 0.4241(3) 0.85033(10) 0.07514(7) 0.0220(2) Uani 1 1 d . . .
C14 C 0.3238(3) 0.75948(12) 0.14586(8) 0.0195(3) Uani 1 1 d . . .
H14 H 0.182(4) 0.7940(15) 0.1949(10) 0.026(4) Uiso 1 1 d . . .
C15 C 0.4106(3) 0.62480(11) 0.15032(8) 0.0155(2) Uani 1 1 d . . .
C16 C 0.6055(3) 0.59016(12) 0.07516(8) 0.0176(2) Uani 1 1 d . . .
H16 H 0.680(4) 0.4980(15) 0.0739(10) 0.023(4) Uiso 1 1 d . . .
C21 C -0.0342(3) 0.19334(11) 0.29235(8) 0.0155(2) Uani 1 1 d . . .
C22 C -0.0999(3) 0.10153(12) 0.37185(9) 0.0201(3) Uani 1 1 d . . .
H22 H -0.062(4) 0.1193(15) 0.4287(11) 0.026(4) Uiso 1 1 d . . .
C23 C -0.2134(3) -0.01620(13) 0.36919(9) 0.0225(3) Uani 1 1 d . . .
H23 H -0.259(4) -0.0769(16) 0.4242(11) 0.029(4) Uiso 1 1 d . . .
C24 C -0.2616(3) -0.04444(13) 0.28803(9) 0.0205(3) Uani 1 1 d . . .
H24 H -0.340(4) -0.1271(17) 0.2885(11) 0.035(4) Uiso 1 1 d . . .
C25 C -0.1992(3) 0.04601(13) 0.20915(9) 0.0201(3) Uani 1 1 d . . .
H25 H -0.233(4) 0.0273(15) 0.1510(11) 0.026(4) Uiso 1 1 d . . .
C26 C -0.0874(3) 0.16436(12) 0.21119(8) 0.0179(2) Uani 1 1 d . . .
H26 H -0.057(4) 0.2240(15) 0.1579(11) 0.021(4) Uiso 1 1 d . . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 1.00 0.0250
0.00 0.00 -1.00 0.0250
0.00 -1.00 0.00 0.0850
0.00 1.00 0.00 0.0850
1.00 0.00 0.00 0.2100
-1.00 0.00 0.00 0.2100
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C7 116.42(9) . . ?
C6 N1 N2 120.30(10) . . ?
C3 N2 N1 119.95(10) . . ?
N2 C3 O1 118.33(11) . . ?
N2 C3 C4 123.87(11) . . ?
O1 C3 C4 117.79(10) . . ?
C5 C4 C3 115.11(10) . . ?
C5 C4 C15 122.39(11) . . ?
C3 C4 C15 122.50(11) . . ?
C4 C5 C6 119.51(11) . . ?
C4 C5 H5 119.2(8) . . ?
C6 C5 H5 121.3(8) . . ?
N1 C6 C5 121.23(11) . . ?
N1 C6 C21 115.79(10) . . ?
C5 C6 C21 122.97(11) . . ?
O1 C7 H71 108.4(10) . . ?
O1 C7 H72 110.4(10) . . ?
H71 C7 H72 112.3(14) . . ?
O1 C7 H73 105.2(9) . . ?
H71 C7 H73 109.7(13) . . ?
H72 C7 H73 110.5(13) . . ?
C12 N11 C16 115.59(11) . . ?
N13 C12 N11 127.12(12) . . ?
N13 C12 H12 115.6(9) . . ?
N11 C12 H12 117.2(9) . . ?
C12 N13 C14 115.83(11) . . ?
N13 C14 C15 122.88(12) . . ?
N13 C14 H14 115.3(9) . . ?
C15 C14 H14 121.8(9) . . ?
C16 C15 C14 115.48(11) . . ?
C16 C15 C4 121.84(11) . . ?
C14 C15 C4 122.67(11) . . ?
N11 C16 C15 123.09(11) . . ?
N11 C16 H16 116.7(9) . . ?
C15 C16 H16 120.1(9) . . ?
C26 C21 C22 118.65(11) . . ?
C26 C21 C6 121.76(11) . . ?
C22 C21 C6 119.60(11) . . ?
C23 C22 C21 120.29(12) . . ?
C23 C22 H22 119.9(9) . . ?
C21 C22 H22 119.8(9) . . ?
C24 C23 C22 120.50(12) . . ?
C24 C23 H23 120.6(10) . . ?
C22 C23 H23 118.9(10) . . ?
C25 C24 C23 119.61(12) . . ?
C25 C24 H24 122.0(10) . . ?
C23 C24 H24 118.4(10) . . ?
C24 C25 C26 120.29(12) . . ?
C24 C25 H25 120.4(9) . . ?
C26 C25 H25 119.3(9) . . ?
C25 C26 C21 120.65(12) . . ?
C25 C26 H26 118.4(9) . . ?
C21 C26 H26 120.9(9) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.3476(14) . ?
O1 C7 1.4512(15) . ?
N1 C6 1.3310(15) . ?
N1 N2 1.3469(14) . ?
N2 C3 1.3201(15) . ?
C3 C4 1.4188(16) . ?
C4 C5 1.3785(16) . ?
C4 C15 1.4807(16) . ?
C5 C6 1.4134(16) . ?
C5 H5 0.974(15) . ?
C6 C21 1.4853(16) . ?
C7 H71 0.976(17) . ?
C7 H72 0.975(18) . ?
C7 H73 0.976(16) . ?
N11 C12 1.3390(17) . ?
N11 C16 1.3421(15) . ?
C12 N13 1.3357(17) . ?
C12 H12 0.960(16) . ?
N13 C14 1.3407(16) . ?
C14 C15 1.3979(17) . ?
C14 H14 0.984(15) . ?
C15 C16 1.3938(17) . ?
C16 H16 0.975(15) . ?
C21 C26 1.3955(17) . ?
C21 C22 1.4021(17) . ?
C22 C23 1.3912(17) . ?
C22 H22 0.967(16) . ?
C23 C24 1.3867(18) . ?
C23 H23 0.956(16) . ?
C24 C25 1.3857(18) . ?
C24 H24 0.965(17) . ?
C25 C26 1.3920(17) . ?
C25 H25 0.986(16) . ?
C26 H26 0.921(15) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 O1 C3 N2 0.34(16) . . . . ?
N1 C6 C21 C22 -8.58(16) . . . . ?
C16 C15 C4 C5 -35.89(17) . . . . ?
C5 C6 C21 C26 -8.33(17) . . . . ?
C3 C4 C15 C14 -37.90(17) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658653
