#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/39/2003912.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_2003912
loop_
_publ_author_name
'Karolak-Wojciechowska, J.'
'Trzezwinska, H. B.'
'Lange, J.'
'Wieczorek, M.'
_publ_section_title
;
 Bicyclic [b]-Heteroannulated Pyridazine Derivatives. 3.
 Partially Hydrogenated Triazolo[4,3-b]pyridazines
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1829
_journal_page_last               1832
_journal_paper_doi               10.1107/S0108270195002848
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C19 H15 F3 N4 O1'
_chemical_formula_sum            'C19 H15 F3 N4 O'
_chemical_formula_weight         372.35
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_type_scat_source           'SHELXTL/PC (Sheldrick, 1990)'
_cell_angle_alpha                90
_cell_angle_beta                 104.43(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.397(4)
_cell_length_b                   9.696(3)
_cell_length_c                   12.140(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      42
_cell_measurement_theta_min      42
_cell_volume                     1755.2(8)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3866
_diffrn_reflns_theta_max         75
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.91
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       needles
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.296
_refine_ls_extinction_coef       'g = 0.002'
_refine_ls_extinction_method     empirical
_refine_ls_goodness_of_fit_obs   5.4
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     245
_refine_ls_number_reflns         1786
_refine_ls_R_factor_obs          0.073
_refine_ls_shift/esd_max         0.02
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/σ²(F)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.071
_reflns_number_observed          1786
_reflns_number_total             3490
_reflns_observed_criterion       F>4\s(F)
_cod_data_source_file            ka1108.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/\s^2^(F)' was changed to
'calc'. New tag '_refine_ls_weighting_details' was created. The value
of the new tag was set to 'w = 1/\s^2^(F)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C19 H15 F3 N4 O1'
_cod_database_code               2003912
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x,1/2-y,1/2+z
-x,-y,-z
-x,1/2+y,1/2-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
N1 .5316(3) -.1819(4) .9228(4) .067(1)
N2 .6005(3) -.2393(4) 1.0065(4) .062(1)
C3 .6762(3) -.1914(5) .9942(4) .051(1)
N4 .6613(2) -.1032(4) .9047(3) .051(1)
N5 .7278(2) -.0281(4) .8696(3) .051(1)
C6 .6946(3) .0318(5) .7754(4) .048(1)
C7 .6005(3) .0314(5) .7059(4) .055(1)
C8 .5312(3) .0050(6) .7714(5) .075(2)
C8a .5718(3) -.1004(5) .8630(4) .061(2)
O6 .7496(2) .1038(3) .7267(3) .052(1)
C31 .7635(4) -.2249(6) 1.0650(5) .071(2)
F1 .8199(2) -.2734(4) 1.0091(3) .110(1)
F2 .8052(2) -.1164(4) 1.1200(3) .100(1)
F3 .7581(2) -.3153(4) 1.1432(4) .132(1)
C61 .8436(3) .1011(5) .7844(4) .064(2)
C62 .8941(3) .1625(6) .7070(4) .055(1)
C63 .9584(4) .0893(7) .6753(5) .093(2)
C64 1.0068(4) .1483(8) .6051(6) .111(3)
C65 .9901(4) .2801(6) .5677(5) .080(2)
C66 .9251(4) .3511(5) .5979(5) .071(2)
C67 .8780(4) .2955(5) .6679(5) .067(2)
C81 .4399(3) -.0379(6) .7035(4) .060(1)
C82 .4255(4) -.1325(5) .6146(5) .062(2)
C83 .3418(4) -.1652(6) .5567(5) .080(2)
C84 .2709(4) -.1071(8) .5818(6) .097(2)
C85 .2815(4) -.0118(8) .6668(6) .097(3)
C86 .3652(4) .0251(6) .7291(5) .082(2)
H71 .595 -.040 .650 .09
H72 .588 .117 .667 .09
H8 .524 .090 .809 .11
H611 .863 .008 .803 .11
H612 .854 .153 .853 .11
H63 .970 -.003 .701 .14
H64 1.052 .095 .583 .15
H65 1.024 .322 .521 .12
H66 .911 .442 .569 .11
H67 .834 .349 .691 .11
H82 .476 -.174 .595 .10
H83 .333 -.230 .496 .13
H84 .212 -.131 .540 .14
H85 .230 .029 .684 .13
H86 .373 .091 .789 .13
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
N2 N1 C8a 105.2(4) no
N1 N2 C3 108.5(4) no
N2 C3 N4 109.9(4) no
N2 C3 C31 125.7(5) no
N4 C3 C31 124.5(4) no
C3 N4 N5 125.3(4) no
C3 N4 C8a 105.5(4) no
N5 N4 C8a 129.2(4) no
N4 N5 C6 110.4(4) yes
N5 C6 C7 128.8(4) yes
N5 C6 O6 118.5(4) yes
C7 C6 O6 112.7(4) yes
C6 C7 C8 115.0(4) no
C7 C8 C8a 106.4(4) no
C7 C8 C81 116.7(4) no
C8a C8 C81 111.8(4) no
N1 C8a N4 110.9(4) no
N1 C8a C8 129.5(5) no
N4 C8a C8 118.9(4) no
C6 O6 C61 116.4(4) no
O6 C61 C62 107.9(4) no
C3 C31 F1 114.4(5) no
C3 C31 F2 112.6(5) no
C3 C31 F3 111.3(5) no
F1 C31 F2 104.1(5) no
F1 C31 F3 107.6(5) no
F2 C31 F3 106.2(5) no
C61 C62 C63 120.4(5) no
C61 C62 C67 121.1(5) no
C63 C62 C67 118.5(5) no
C62 C63 C64 120.2(6) no
C63 C64 C65 120.4(6) no
C64 C65 C66 119.0(6) no
C65 C66 C67 121.3(6) no
C62 C67 C66 120.6(5) no
C8 C81 C82 123.7(5) no
C8 C81 C86 117.8(5) no
C82 C81 C86 118.5(5) no
C81 C82 C83 120.5(5) no
C82 C83 C84 121.1(6) no
C83 C84 C85 120.6(7) no
C84 C85 C86 120.9(6) no
C81 C86 C85 118.4(6) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 N2 1.394(6) no
N1 C8a 1.331(7) no
N2 C3 1.303(7) no
C3 N4 1.361(6) no
C3 C31 1.446(7) no
N4 N5 1.412(5) yes
N4 C8a 1.350(5) no
N5 C6 1.274(6) yes
C6 C7 1.490(6) no
C6 O6 1.348(6) yes
C7 C8 1.508(8) no
C8 C8a 1.530(7) no
C8 C81 1.506(6) no
O6 C61 1.448(5) yes
C61 C62 1.490(8) yes
C31 F1 1.320(8) no
C31 F2 1.328(7) no
C31 F3 1.314(8) no
C62 C63 1.355(9) no
C62 C67 1.381(8) no
C63 C64 1.392(10) no
C64 C65 1.365(10) no
C65 C66 1.344(9) no
C66 C67 1.363(9) no
C81 C82 1.396(8) no
C81 C86 1.410(8) no
C82 C83 1.348(8) no
C83 C84 1.335(10) no
C84 C85 1.369(11) no
C85 C86 1.375(8) no
