#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/46/4024677.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_4024677
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         'C12 H19 N5 O2'
_chemical_formula_sum            'C12 H19 N5 O2'
_chemical_formula_weight         265.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_audit_creation_method
;
manual editing of the CIF file 
created by SHELXTL Ver. 6.14
and processed with modiCIfer-09152005. 
;
_cell_angle_alpha                101.189(10)
_cell_angle_beta                 112.835(10)
_cell_angle_gamma                102.974(10)
_cell_formula_units_Z            2
_cell_length_a                   7.9081(11)
_cell_length_b                   9.3887(11)
_cell_length_c                   10.1211(18)
_cell_measurement_reflns_used    4724
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.48
_cell_measurement_theta_min      2.30
_cell_volume                     640.96(16)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_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      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'R-AXIS SPIDER'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10082
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9951
_exptl_absorpt_correction_T_min  0.9732
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
NUMABS (Rigaku Inc., 2007)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.090(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3381
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0664
_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)+(0.1000P)²+0.0800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1649
_refine_ls_wR_factor_ref         0.1733
_reflns_number_gt                2881
_reflns_number_total             3381
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9006943_si_006.cif
_cod_data_source_block           12a_s081
_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_original_sg_symbol_Hall     '-P 1        '
_cod_original_sg_symbol_H-M      'P -1        '
_cod_database_code               4024677
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 0.06441(14) 0.85341(12) 0.57344(14) 0.0462(3) Uani 1 1 d . . .
O2 O 0.28953(18) 0.52828(13) 0.86172(16) 0.0571(4) Uani 1 1 d . . .
N1 N 0.44487(17) 1.17980(13) 0.63596(14) 0.0381(3) Uani 1 1 d . . .
N2 N 0.26911(17) 1.07143(13) 0.58681(15) 0.0393(3) Uani 1 1 d . . .
N3 N 0.75670(16) 0.95569(14) 0.77698(15) 0.0411(3) Uani 1 1 d . . .
N4 N 0.77791(17) 1.24933(14) 0.74660(15) 0.0424(3) Uani 1 1 d . . .
N5 N 0.39159(15) 0.76179(12) 0.73908(13) 0.0337(3) Uani 1 1 d . . .
C1 C 0.23578(19) 0.93404(15) 0.61365(16) 0.0350(3) Uani 1 1 d . . .
C2 C 0.40643(18) 0.89339(14) 0.68918(15) 0.0326(3) Uani 1 1 d . . .
C3 C 0.58768(18) 0.98990(14) 0.72074(15) 0.0325(3) Uani 1 1 d . . .
C4 C 0.59762(19) 1.14073(15) 0.69912(15) 0.0337(3) Uani 1 1 d . . .
C5 C 0.9429(2) 1.07185(19) 0.8215(2) 0.0456(4) Uani 1 1 d . . .
C6 C 0.9362(2) 1.23140(18) 0.86911(19) 0.0457(4) Uani 1 1 d . . .
C7 C 0.7560(2) 0.79732(18) 0.7328(2) 0.0453(4) Uani 1 1 d . . .
C8 C 0.7823(3) 1.40738(19) 0.7575(3) 0.0548(5) Uani 1 1 d . . .
C9 C 0.2230(2) 0.62182(16) 0.6470(2) 0.0494(4) Uani 1 1 d . . .
C10 C 0.2597(3) 0.49196(17) 0.7092(2) 0.0548(5) Uani 1 1 d . . .
C11 C 0.4565(3) 0.66100(19) 0.9515(2) 0.0545(5) Uani 1 1 d . . .
C12 C 0.4324(3) 0.79795(17) 0.89748(18) 0.0451(4) Uani 1 1 d . . .
H2N H 0.172(3) 1.104(2) 0.545(2) 0.060(6) Uiso 1 1 d . . .
H51 H 0.976(3) 1.056(2) 0.737(3) 0.065(6) Uiso 1 1 d . . .
H52 H 1.042(3) 1.056(2) 0.903(2) 0.050(5) Uiso 1 1 d . . .
H61 H 1.053(3) 1.301(2) 0.888(2) 0.051(5) Uiso 1 1 d . . .
H62 H 0.925(3) 1.255(2) 0.963(2) 0.053(5) Uiso 1 1 d . . .
H71 H 0.739(3) 0.744(3) 0.799(3) 0.070(6) Uiso 1 1 d . . .
H72 H 0.881(4) 0.799(3) 0.742(3) 0.087(8) Uiso 1 1 d . . .
H73 H 0.664(4) 0.743(3) 0.637(3) 0.080(7) Uiso 1 1 d . . .
H81 H 0.695(3) 1.413(3) 0.657(3) 0.071(7) Uiso 1 1 d . . .
H82 H 0.907(4) 1.471(3) 0.784(3) 0.088(8) Uiso 1 1 d . . .
H83 H 0.744(4) 1.452(3) 0.837(3) 0.091(8) Uiso 1 1 d . . .
H91 H 0.085(3) 0.629(2) 0.643(2) 0.068(6) Uiso 1 1 d . . .
H92 H 0.207(3) 0.595(3) 0.544(3) 0.066(6) Uiso 1 1 d . . .
H101 H 0.374(3) 0.470(3) 0.704(2) 0.065(6) Uiso 1 1 d . . .
H102 H 0.145(3) 0.393(2) 0.660(2) 0.055(5) Uiso 1 1 d . . .
H111 H 0.575(3) 0.642(2) 0.945(2) 0.057(5) Uiso 1 1 d . . .
H112 H 0.477(3) 0.678(3) 1.055(3) 0.076(7) Uiso 1 1 d . . .
H121 H 0.546(3) 0.888(2) 0.952(2) 0.059(5) Uiso 1 1 d . . .
H122 H 0.331(3) 0.828(3) 0.914(3) 0.067(6) 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_
_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
C11 O2 C10 109.19(13) . . yes
C4 N1 N2 116.66(11) . . yes
C1 N2 N1 126.79(12) . . yes
C1 N2 H2N 119.9(15) . . ?
N1 N2 H2N 112.7(15) . . ?
C3 N3 C5 119.95(12) . . yes
C3 N3 C7 120.81(12) . . yes
C5 N3 C7 113.61(12) . . yes
C4 N4 C6 114.24(12) . . yes
C4 N4 C8 116.53(13) . . yes
C6 N4 C8 115.46(13) . . yes
C2 N5 C12 113.05(10) . . yes
C2 N5 C9 119.63(11) . . yes
C12 N5 C9 110.77(13) . . yes
O1 C1 N2 119.02(12) . . yes
O1 C1 C2 125.05(12) . . yes
N2 C1 C2 115.92(12) . . yes
C3 C2 N5 119.92(11) . . yes
C3 C2 C1 119.13(12) . . yes
N5 C2 C1 120.85(12) . . yes
N3 C3 C2 124.34(12) . . yes
N3 C3 C4 118.76(11) . . yes
C2 C3 C4 116.82(11) . . yes
N1 C4 N4 117.17(12) . . yes
N1 C4 C3 123.46(12) . . yes
N4 C4 C3 119.37(12) . . yes
N3 C5 C6 111.16(12) . . yes
N3 C5 H51 108.9(13) . . ?
C6 C5 H51 111.4(13) . . ?
N3 C5 H52 108.8(12) . . ?
C6 C5 H52 110.1(11) . . ?
H51 C5 H52 106.4(17) . . ?
N4 C6 C5 108.67(13) . . yes
N4 C6 H61 109.6(12) . . ?
C5 C6 H61 108.1(12) . . ?
N4 C6 H62 111.8(12) . . ?
C5 C6 H62 112.8(12) . . ?
H61 C6 H62 105.8(17) . . ?
N3 C7 H71 112.5(14) . . ?
N3 C7 H72 109.1(16) . . ?
H71 C7 H72 104(2) . . ?
N3 C7 H73 112.0(17) . . ?
H71 C7 H73 109(2) . . ?
H72 C7 H73 110(2) . . ?
N4 C8 H81 110.5(13) . . ?
N4 C8 H82 110.4(17) . . ?
H81 C8 H82 106(2) . . ?
N4 C8 H83 112.0(15) . . ?
H81 C8 H83 110(2) . . ?
H82 C8 H83 107(2) . . ?
N5 C9 C10 108.98(13) . . yes
N5 C9 H91 115.5(12) . . ?
C10 C9 H91 106.7(12) . . ?
N5 C9 H92 108.9(13) . . ?
C10 C9 H92 108.5(13) . . ?
H91 C9 H92 108.1(18) . . ?
O2 C10 C9 110.64(14) . . yes
O2 C10 H101 109.6(13) . . ?
C9 C10 H101 110.9(13) . . ?
O2 C10 H102 101.2(11) . . ?
C9 C10 H102 114.7(11) . . ?
H101 C10 H102 109.5(16) . . ?
O2 C11 C12 111.25(14) . . yes
O2 C11 H111 109.9(12) . . ?
C12 C11 H111 107.4(12) . . ?
O2 C11 H112 106.9(15) . . ?
C12 C11 H112 113.0(14) . . ?
H111 C11 H112 108.5(19) . . ?
N5 C12 C11 110.06(13) . . yes
N5 C12 H121 106.9(13) . . ?
C11 C12 H121 113.3(13) . . ?
N5 C12 H122 111.9(14) . . ?
C11 C12 H122 109.9(14) . . ?
H121 C12 H122 104.8(18) . . ?
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 C1 1.2518(16) . yes
O2 C11 1.419(2) . yes
O2 C10 1.426(2) . yes
N1 C4 1.3012(18) . yes
N1 N2 1.3589(15) . yes
N2 C1 1.3587(17) . yes
N2 H2N 0.88(2) . ?
N3 C3 1.3737(17) . yes
N3 C5 1.4607(18) . yes
N3 C7 1.4654(19) . yes
N4 C4 1.3888(17) . yes
N4 C6 1.450(2) . yes
N4 C8 1.458(2) . yes
N5 C2 1.4208(16) . yes
N5 C12 1.459(2) . yes
N5 C9 1.4650(17) . yes
C1 C2 1.4474(18) . yes
C2 C3 1.3880(17) . yes
C3 C4 1.4639(18) . yes
C5 C6 1.501(2) . yes
C5 H51 0.98(2) . ?
C5 H52 0.96(2) . ?
C6 H61 0.93(2) . ?
C6 H62 0.98(2) . ?
C7 H71 0.94(3) . ?
C7 H72 0.96(3) . ?
C7 H73 0.91(3) . ?
C8 H81 1.00(3) . ?
C8 H82 0.93(3) . ?
C8 H83 1.02(3) . ?
C9 C10 1.511(2) . yes
C9 H91 1.09(2) . ?
C9 H92 0.97(2) . ?
C10 H101 0.99(2) . ?
C10 H102 1.01(2) . ?
C11 C12 1.514(2) . yes
C11 H111 1.02(2) . ?
C11 H112 0.97(3) . ?
C12 H121 0.96(2) . ?
C12 H122 0.97(2) . ?
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 0.88(2) 1.97(2) 2.8364(16) 172(2) 2_576
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
C4 N1 N2 C1 9.2(2) . . . . yes
N1 N2 C1 O1 172.77(13) . . . . yes
N1 N2 C1 C2 -6.8(2) . . . . yes
C12 N5 C2 C3 80.44(16) . . . . yes
C9 N5 C2 C3 -146.29(15) . . . . yes
C12 N5 C2 C1 -95.68(15) . . . . yes
C9 N5 C2 C1 37.58(19) . . . . yes
O1 C1 C2 C3 176.75(13) . . . . yes
N2 C1 C2 C3 -3.7(2) . . . . yes
O1 C1 C2 N5 -7.1(2) . . . . yes
N2 C1 C2 N5 172.47(12) . . . . yes
C5 N3 C3 C2 -173.45(14) . . . . yes
C7 N3 C3 C2 34.7(2) . . . . yes
C5 N3 C3 C4 3.2(2) . . . . yes
C7 N3 C3 C4 -148.59(14) . . . . yes
N5 C2 C3 N3 11.1(2) . . . . yes
C1 C2 C3 N3 -172.74(13) . . . . yes
N5 C2 C3 C4 -165.69(12) . . . . yes
C1 C2 C3 C4 10.50(19) . . . . yes
N2 N1 C4 N4 178.53(12) . . . . yes
N2 N1 C4 C3 -1.0(2) . . . . yes
C6 N4 C4 N1 154.23(14) . . . . yes
C8 N4 C4 N1 15.5(2) . . . . yes
C6 N4 C4 C3 -26.23(19) . . . . yes
C8 N4 C4 C3 -164.98(15) . . . . yes
N3 C3 C4 N1 174.54(13) . . . . yes
C2 C3 C4 N1 -8.5(2) . . . . yes
N3 C3 C4 N4 -5.0(2) . . . . yes
C2 C3 C4 N4 171.98(12) . . . . yes
C3 N3 C5 C6 27.7(2) . . . . yes
C7 N3 C5 C6 -178.59(15) . . . . yes
C4 N4 C6 C5 56.34(18) . . . . yes
C8 N4 C6 C5 -164.46(15) . . . . yes
N3 C5 C6 N4 -56.4(2) . . . . yes
C2 N5 C9 C10 169.72(14) . . . . yes
C12 N5 C9 C10 -56.06(19) . . . . yes
C11 O2 C10 C9 -61.84(18) . . . . yes
N5 C9 C10 O2 59.8(2) . . . . yes
C10 O2 C11 C12 60.1(2) . . . . yes
C2 N5 C12 C11 -167.91(13) . . . . yes
C9 N5 C12 C11 54.70(17) . . . . yes
O2 C11 C12 N5 -56.9(2) . . . . yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658995
