#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/79/2207956.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_2207956
loop_
_publ_author_name
'Dilek, Nefise'
'Güneş, Bilal'
'Şahin, Ertan'
'Ide, Semra'
'Ünlü, Serdar'
_publ_section_title
;
 6-[3-Phenyl-5-(trifluoromethyl)pyrazol-1-yl]pyridazin-3(2H)-one
;
_journal_coeditor_code           AT2001
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o446
_journal_page_last               o448
_journal_paper_doi               10.1107/S160053680504256X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H9 F3 N4 O1'
_chemical_formula_moiety         'C14 H9 F3 N4 O1'
_chemical_formula_sum            'C14 H9 F3 N4 O'
_chemical_formula_weight         306.25
_chemical_name_systematic
;
6-[3-Phenyl-5-(trifluoromethyl)pyrazol-1-yl]pyridazin-3(2H)-one
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                82.97(3)
_cell_angle_beta                 74.84(3)
_cell_angle_gamma                84.95(3)
_cell_formula_units_Z            2
_cell_length_a                   7.603(2)
_cell_length_b                   8.079(2)
_cell_length_c                   11.202(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      74.24
_cell_measurement_theta_min      4.11
_cell_volume                     658.0(3)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2839
_diffrn_reflns_theta_full        74.24
_diffrn_reflns_theta_max         74.24
_diffrn_reflns_theta_min         4.11
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.141
_exptl_absorpt_correction_T_max  0.7259
_exptl_absorpt_correction_T_min  0.6582
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0470
_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)+(0.1019P)²+0.0709P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1406
_reflns_number_gt                1979
_reflns_number_total             2555
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2001.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C14 H9 F3 N4 O1'
_cod_database_code               2207956
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
-x,-y,-z
loop_
_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
_atom_site_type_symbol
C1 0.2938(3) -0.4488(2) 1.13582(18) 0.0463(4) Uani d 1 C
C2 0.1313(3) -0.3913(2) 1.1007(2) 0.0534(5) Uani d 1 C
C3 0.1241(3) -0.2370(3) 1.0412(2) 0.0568(5) Uani d 1 C
C4 0.2788(3) -0.1348(2) 1.01490(19) 0.0512(5) Uani d 1 C
C5 0.4237(3) -0.6724(2) 1.27347(19) 0.0495(4) Uani d 1 C
C6 0.5696(3) -0.5850(3) 1.3019(2) 0.0583(5) Uani d 1 C
C7 0.3721(3) -0.8290(2) 1.3213(2) 0.0539(5) Uani d 1 C
C8 0.2182(3) -0.8535(2) 1.27909(18) 0.0496(4) Uani d 1 C
C9 0.1033(3) -0.9978(2) 1.31147(19) 0.0499(5) Uani d 1 C
C10 0.1569(3) -1.1399(3) 1.3798(2) 0.0627(6) Uani d 1 C
C11 0.0464(4) -1.2738(3) 1.4165(3) 0.0702(7) Uani d 1 C
C12 -0.1156(4) -1.2688(3) 1.3852(2) 0.0659(6) Uani d 1 C
C13 -0.1695(3) -1.1301(3) 1.3154(2) 0.0652(6) Uani d 1 C
C14 -0.0602(3) -0.9949(3) 1.2787(2) 0.0580(5) Uani d 1 C
N1 0.4381(2) -0.36511(19) 1.11129(17) 0.0527(4) Uani d 1 N
N2 0.4271(2) -0.2098(2) 1.05103(18) 0.0538(4) Uani d 1 N
N3 0.3045(2) -0.60768(18) 1.20470(15) 0.0485(4) Uani d 1 N
N4 0.1778(2) -0.71823(19) 1.20758(16) 0.0515(4) Uani d 1 N
O1 0.2841(2) 0.01111(18) 0.96438(16) 0.0671(5) Uani d 1 O
F1 0.6319(2) -0.67911(18) 1.39104(15) 0.0837(5) Uani d 1 F
F2 0.5104(2) -0.43810(16) 1.34564(14) 0.0744(4) Uani d 1 F
F3 0.71366(17) -0.55744(18) 1.20686(15) 0.0775(4) Uani d 1 F
H1 0.031(4) -0.467(3) 1.117(2) 0.077(7) Uiso d 1 H
H2 0.538(4) -0.148(3) 1.046(2) 0.079(8) Uiso d 1 H
H3 0.026(4) -0.189(4) 1.020(3) 0.089(9) Uiso d 1 H
H7 0.429(3) -0.899(3) 1.381(2) 0.073(7) Uiso d 1 H
H10 0.265(3) -1.139(3) 1.400(2) 0.062(6) Uiso d 1 H
H11 0.085(4) -1.362(4) 1.463(3) 0.098(10) Uiso d 1 H
H12 -0.191(4) -1.358(4) 1.409(3) 0.096(9) Uiso d 1 H
H13 -0.280(3) -1.126(3) 1.292(2) 0.060(6) Uiso d 1 H
H14 -0.100(3) -0.896(3) 1.233(2) 0.063(6) Uiso d 1 H
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'
F F 0.0727 0.0534 '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
_geom_angle_publ_flag
N4 N3 C5 111.44(15) yes
N4 N3 C1 118.10(15) yes
C5 N3 C1 130.45(16) yes
C1 N1 N2 116.18(16) yes
C8 N4 N3 105.40(15) yes
N1 N2 C4 126.27(16) yes
N1 N2 H2 110.8(15) ?
C4 N2 H2 122.4(15) ?
N1 C1 C2 124.50(17) ?
N1 C1 N3 115.41(16) yes
C2 C1 N3 120.08(17) ?
C14 C9 C10 118.65(19) ?
C14 C9 C8 121.75(17) ?
C10 C9 C8 119.57(18) ?
C2 C3 C4 120.13(19) ?
C2 C3 H3 124.0(19) ?
C4 C3 H3 115.8(19) ?
O1 C4 N2 119.92(18) yes
O1 C4 C3 125.26(18) ?
N2 C4 C3 114.82(17) ?
N4 C8 C7 110.35(17) ?
N4 C8 C9 121.68(17) ?
C7 C8 C9 127.85(17) ?
C3 C2 C1 118.02(19) ?
C3 C2 H1 122.4(15) ?
C1 C2 H1 119.5(15) ?
C5 C7 C8 106.27(18) ?
C5 C7 H7 122.7(15) ?
C8 C7 H7 130.6(15) ?
C13 C14 C9 120.4(2) ?
C13 C14 H14 120.3(15) ?
C9 C14 H14 119.2(15) ?
C7 C5 N3 106.53(17) ?
C7 C5 C6 125.89(19) ?
N3 C5 C6 127.31(17) ?
C9 C10 C11 120.5(2) ?
C9 C10 H10 117.3(15) ?
C11 C10 H10 122.2(15) ?
F3 C6 F2 107.08(18) yes
F3 C6 F1 106.23(18) yes
F2 C6 F1 106.37(19) yes
F3 C6 C5 114.65(19) yes
F2 C6 C5 113.01(17) yes
F1 C6 C5 108.98(17) yes
C12 C11 C10 120.4(2) ?
C12 C11 H11 122(2) ?
C10 C11 H11 117(2) ?
C11 C12 C13 119.9(2) ?
C11 C12 H12 121.5(19) ?
C13 C12 H12 118.6(19) ?
C14 C13 C12 120.1(2) ?
C14 C13 H13 119.2(15) ?
C12 C13 H13 120.7(15) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 1.243(2) yes
F2 C6 1.336(3) yes
N3 N4 1.362(2) yes
N3 C5 1.368(2) yes
N3 C1 1.422(2) yes
F3 C6 1.326(3) yes
N1 C1 1.290(2) yes
N1 N2 1.357(2) yes
N4 C8 1.336(2) yes
F1 C6 1.341(2) yes
N2 C4 1.363(3) yes
N2 H2 1.01(3) ?
C1 C2 1.416(3) ?
C9 C14 1.383(3) ?
C9 C10 1.392(3) ?
C9 C8 1.471(3) ?
C3 C2 1.344(3) ?
C3 C4 1.444(3) ?
C3 H3 0.88(3) ?
C8 C7 1.409(3) ?
C2 H1 0.99(3) ?
C7 C5 1.362(3) ?
C7 H7 0.99(2) ?
C14 C13 1.387(3) ?
C14 H14 0.96(2) ?
C5 C6 1.486(3) ?
C10 C11 1.385(3) ?
C10 H10 0.91(2) ?
C11 C12 1.362(4) ?
C11 H11 0.91(3) ?
C12 C13 1.381(3) ?
C12 H12 0.93(3) ?
C13 H13 0.94(2) ?
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
N2 H2 O1 2_657 1.00(3) 1.79(3) 2.790(2) 172(2) yes
C2 H1 F3 1_455 0.99(3) 2.50(3) 3.418(3) 156(2) 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
_geom_torsion_publ_flag
C5 N3 N4 C8 0.1(2) ?
C1 N3 N4 C8 -179.13(17) ?
C1 N1 N2 C4 0.3(3) ?
N2 N1 C1 C2 2.1(3) ?
N2 N1 C1 N3 -176.82(17) yes
N4 N3 C1 N1 -164.22(18) yes
C5 N3 C1 N1 16.8(3) yes
N4 N3 C1 C2 16.8(3) yes
C5 N3 C1 C2 -162.3(2) yes
N1 N2 C4 O1 177.2(2) yes
N1 N2 C4 C3 -2.3(3) ?
C2 C3 C4 O1 -177.4(2) yes
C2 C3 C4 N2 2.1(3) ?
N3 N4 C8 C7 -0.3(2) ?
N3 N4 C8 C9 175.91(17) ?
C14 C9 C8 N4 -5.7(3) yes
C10 C9 C8 N4 176.1(2) ?
C14 C9 C8 C7 169.8(2) ?
C10 C9 C8 C7 -8.4(3) ?
C4 C3 C2 C1 -0.1(4) ?
N1 C1 C2 C3 -2.2(3) ?
N3 C1 C2 C3 176.7(2) ?
N4 C8 C7 C5 0.5(2) ?
C9 C8 C7 C5 -175.5(2) ?
C10 C9 C14 C13 1.2(4) ?
C8 C9 C14 C13 -177.0(2) ?
C8 C7 C5 N3 -0.4(2) ?
C8 C7 C5 C6 174.1(2) ?
N4 N3 C5 C7 0.2(2) ?
C1 N3 C5 C7 179.28(19) ?
N4 N3 C5 C6 -174.14(19) yes
C1 N3 C5 C6 4.9(4) yes
C14 C9 C10 C11 -1.5(4) ?
C8 C9 C10 C11 176.8(2) ?
C7 C5 C6 F3 113.4(2) yes
N3 C5 C6 F3 -73.3(3) yes
C7 C5 C6 F2 -123.5(2) yes
N3 C5 C6 F2 49.8(3) yes
C7 C5 C6 F1 -5.4(3) yes
N3 C5 C6 F1 167.9(2) yes
C9 C10 C11 C12 0.6(4) ?
C10 C11 C12 C13 0.6(4) ?
C9 C14 C13 C12 0.0(4) ?
C11 C12 C13 C14 -0.9(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126619
