#------------------------------------------------------------------------------
#$Date: 2017-10-13 13:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201982 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/46/4024673.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_4024673
loop_
_publ_author_name
'Graham Pattison'
'Graham Sandford'
'Dmitry S. Yufit'
'Judith A. K. Howard'
'John A. Christopher'
'David D. Miller'
_publ_contact_author_address
;
Department of Chemistry
University of Durham
South Rd.
Durham
DH1 3LE
UK
;
_publ_contact_author_email       d.s.yufit@durham.ac.uk
_publ_contact_author_fax         '0191 384 4737'
_publ_contact_author_name        'Dmitry Yufit'
_publ_contact_author_phone       '0191 334 2004'
_publ_section_title
;
Polysubstituted Pyridazinones from Sequential Nucleophilic Substitution
Reactions of Tetrafluoropyridazine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5533
_journal_page_last               5540
_journal_paper_doi               10.1021/jo9006943
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C4 H F3 N2 O'
_chemical_formula_sum            'C4 H F3 N2 O'
_chemical_formula_weight         150.07
_chemical_melting_point          130.0(10)
_chemical_name_systematic
; 
 4,5,6-trifluoropyridazin-3(2H)-one 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
manual editing of the CIF file 
created by SHELXTL Ver. 6.10
and processed with modiCIfer-09152005. 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.17(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5739(15)
_cell_length_b                   4.9342(7)
_cell_length_c                   9.7643(13)
_cell_measurement_reflns_used    1710
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.44
_cell_measurement_theta_min      3.91
_cell_volume                     501.4(1)
_computing_cell_refinement       'SAINT Ver. 6.45  (Bruker-AXS, 2003)'
_computing_data_collection       'SMART Ver. 5.630 (Bruker-AXS, 2003)'
_computing_data_reduction        'SAINT Ver. 6.45'
_computing_molecular_graphics    'SHELXTL Ver. 6.14'
_computing_publication_material  'SHELXTL Ver. 6.14'
_computing_structure_refinement  'SHELXTL Ver. 6.14'
_computing_structure_solution    'SHELXTL Ver. 6.14 (Bruker-AXS, 2003)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Proteum M'
_diffrn_measurement_method       '0.30° ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bede Microsource'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_sigmaI/netI    0.0512
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5156
_diffrn_reflns_theta_full        29.49
_diffrn_reflns_theta_max         29.49
_diffrn_reflns_theta_min         1.96
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.988
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         1385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0473
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1401
_reflns_number_gt                1121
_reflns_number_total             1385
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo9006943_si_002.cif
_cod_data_source_block           1_s281
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_chemical_melting_point' value '129-131' was changed to '130.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_Hall     '-P 2ybc     '
_cod_original_sg_symbol_H-M      'P 1 21/c 1  '
_cod_database_code               4024673
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
F1 F 0.36771(9) 0.91977(19) 0.40897(10) 0.0197(3) Uani 1 1 d . . .
F2 F 0.45348(9) 0.5869(2) 0.63260(10) 0.0211(3) Uani 1 1 d . . .
F3 F 0.30333(10) 0.1674(2) 0.68124(10) 0.0228(3) Uani 1 1 d . . .
O1 O 0.12999(11) 0.8160(3) 0.25587(12) 0.0191(3) Uani 1 1 d . . .
N1 N 0.15015(14) 0.2794(3) 0.50287(14) 0.0173(3) Uani 1 1 d . . .
N2 N 0.10901(13) 0.4513(3) 0.39467(14) 0.0154(3) Uani 1 1 d . . .
C1 C 0.17249(15) 0.6701(3) 0.35589(16) 0.0140(3) Uani 1 1 d . . .
C2 C 0.29722(15) 0.7146(3) 0.44287(16) 0.0140(3) Uani 1 1 d . . .
C3 C 0.34021(15) 0.5525(3) 0.55125(16) 0.0143(3) Uani 1 1 d . . .
C4 C 0.25944(15) 0.3342(3) 0.57595(15) 0.0153(4) Uani 1 1 d . . .
H2N H 0.028(2) 0.400(4) 0.346(2) 0.021(5) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0195(5) 0.0180(5) 0.0218(5) 0.0045(4) 0.0041(4) -0.0054(4)
F2 0.0158(5) 0.0284(6) 0.0167(5) 0.0019(4) -0.0035(4) -0.0036(4)
F3 0.0293(6) 0.0212(5) 0.0164(5) 0.0068(4) 0.0004(4) -0.0018(4)
O1 0.0181(6) 0.0214(6) 0.0170(6) 0.0043(4) 0.0011(5) 0.0034(4)
N1 0.0198(7) 0.0176(7) 0.0149(7) -0.0003(5) 0.0039(5) -0.0019(5)
N2 0.0140(7) 0.0176(7) 0.0139(6) -0.0005(5) 0.0007(5) -0.0007(5)
C1 0.0140(8) 0.0150(7) 0.0134(7) -0.0024(6) 0.0037(6) 0.0026(5)
C2 0.0147(7) 0.0130(7) 0.0152(7) -0.0025(5) 0.0049(6) -0.0016(5)
C3 0.0125(7) 0.0166(8) 0.0134(7) -0.0039(6) 0.0011(5) -0.0002(5)
C4 0.0201(8) 0.0150(7) 0.0110(7) 0.0009(5) 0.0034(6) 0.0014(6)
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'
F F 0.0171 0.0103 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 N2 115.77(14) . . yes
C1 N2 N1 127.12(13) . . yes
C1 N2 H2N 121.5(12) . . ?
N1 N2 H2N 111.4(13) . . ?
O1 C1 N2 123.75(14) . . yes
O1 C1 C2 122.73(15) . . yes
N2 C1 C2 113.51(13) . . yes
F1 C2 C3 121.51(14) . . yes
F1 C2 C1 117.33(13) . . yes
C3 C2 C1 121.15(14) . . yes
F2 C3 C2 122.77(14) . . yes
F2 C3 C4 120.09(14) . . yes
C2 C3 C4 117.13(14) . . yes
N1 C4 F3 117.24(14) . . yes
N1 C4 C3 125.31(14) . . yes
F3 C4 C3 117.41(14) . . yes
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
F1 C2 1.3330(17) . yes
F2 C3 1.3260(18) . yes
F3 C4 1.3346(18) . yes
O1 C1 1.2327(19) . yes
N1 C4 1.275(2) . yes
N1 N2 1.3648(18) . yes
N2 C1 1.360(2) . yes
N2 H2N 0.94(2) . ?
C1 C2 1.454(2) . yes
C2 C3 1.340(2) . yes
C3 C4 1.422(2) . yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N O1 0.94(2) 1.83(2) 2.7714(18) 177.0(19) 2_545
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10328884
