##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_data_validation_number     ?
_journal_date_recd_electronic     2005-10-20
_journal_date_accepted     2005-11-02
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue     12
_journal_page_first     o4030
_journal_page_last     o4031
_journal_paper_category     EO
_journal_coeditor_code     SJ6141
_publ_contact_author_name     'Lingling Wang'
_publ_contact_author_address
;Key Lab of Brain Functional Genomics, MOE & STCSM, East China Normal
University
Shanghai 200062
People's Republic of China
;
_publ_contact_author_email     xiaoshuangyi@eyou.com
_publ_contact_author_fax     '8621 6260 1953'
_publ_contact_author_phone     '8621 6223 3855'
_publ_section_title
;
6-Chloro-2-(4-fluorophenyl)imidazo[1,2-b]pyridazine
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Wang, Lingling' .
;
Key Laboratory of Brain Functional Genomics
MOE & STCSM
East China Normal University
Shanghai 200062
People's Republic of China
;
    'Ma, Mingliang' .
;
Key Laboratory of Brain Functional Genomics
MOE & STCSM
East China Normal University
Shanghai 200062
People's Republic of China
;
    'Shen, Xiaohong' .
;
Key Laboratory of Brain Functional Genomics
MOE & STCSM
East China Normal University
Shanghai 200062
People's Republic of China
;
    'Zhao, Shiguo' .
;
Key Laboratory of Brain Functional Genomics
MOE & STCSM
East China Normal University
Shanghai 200062
People's Republic of China
;
data_I
_chemical_name_systematic
;
6-chloro-2-(4-fluorophenyl)imidazo[1,2-b]pyridazine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H7 Cl F N3'
_chemical_formula_sum     'C12 H7 Cl F N3'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C12 H7 Cl F N3'
_chemical_formula_weight     247.66
_chemical_melting_point     494
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     'P -1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     5.6051(7)
_cell_length_b     7.4946(10)
_cell_length_c     13.2471(17)
_cell_angle_alpha     101.308(2)
_cell_angle_beta     91.883(2)
_cell_angle_gamma     100.565(2)
_cell_volume     535.06(12)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1324
_cell_measurement_theta_min     5.650
_cell_measurement_theta_max     52.437
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.47
_exptl_crystal_size_mid     0.33
_exptl_crystal_size_min     0.27
_exptl_crystal_density_diffrn     1.537
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     252
_exptl_absorpt_coefficient_mu     0.348
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.685
_exptl_absorpt_correction_T_max     0.910
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3153
_diffrn_reflns_av_R_equivalents     0.0831
_diffrn_reflns_av_sigmaI/netI     0.0600
_diffrn_reflns_theta_min     1.57
_diffrn_reflns_theta_max     27.00
_diffrn_reflns_theta_full     27.00
_diffrn_measured_fraction_theta_max     0.971
_diffrn_measured_fraction_theta_full     0.971
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2260
_reflns_number_gt     1695
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0613
_refine_ls_R_factor_gt     0.0505
_refine_ls_wR_factor_gt     0.1245
_refine_ls_wR_factor_ref     0.1306
_refine_ls_goodness_of_fit_ref     0.958
_refine_ls_restrained_S_all     0.958
_refine_ls_number_reflns     2260
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
             'calc w = 1/[σ²(Fo²)+(0.0716P)²] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.296
_refine_diff_density_min     -0.241
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'F' 'F' 0.0171 0.0103
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 1997)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT (Bruker, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1997)'
_computing_publication_material     'SHELXTL'
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_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    Cl1 0.36529(10) 0.81996(8) 1.31801(4) 0.0670(2) Uani d . 1 . . Cl
    F1 -0.1971(3) 0.7435(2) 0.46559(11) 0.1010(6) Uani d . 1 . . F
    N1 -0.2159(3) 0.6766(2) 0.93779(13) 0.0487(4) Uani d . 1 . . N
    N4 0.1221(3) 0.7882(2) 1.04173(12) 0.0451(4) Uani d . 1 . . N
    N5 0.2758(3) 0.8302(2) 1.12816(12) 0.0496(4) Uani d . 1 . . N
    C2 -0.0337(3) 0.7582(2) 0.88491(15) 0.0468(5) Uani d . 1 . . C
    C3 0.1760(3) 0.8278(2) 0.94772(15) 0.0485(5) Uani d . 1 . . C
    H3 0.3235 0.8890 0.9300 0.058 Uiso calc R 1 . . H
    C6 0.1764(3) 0.7742(3) 1.20699(16) 0.0496(5) Uani d . 1 . . C
    C7 -0.0677(3) 0.6793(3) 1.20807(16) 0.0528(5) Uani d . 1 . . C
    H7 -0.1248 0.6450 1.2680 0.063 Uiso calc R 1 . . H
    C8 -0.2143(3) 0.6400(3) 1.12104(16) 0.0514(5) Uani d . 1 . . C
    H8 -0.3744 0.5776 1.1193 0.062 Uiso calc R 1 . . H
    C9 -0.1192(3) 0.6958(2) 1.03229(15) 0.0461(5) Uani d . 1 . . C
    C10 -0.0741(3) 0.7576(2) 0.77545(15) 0.0476(5) Uani d . 1 . . C
    C11 -0.3013(4) 0.6785(3) 0.72334(17) 0.0595(6) Uani d . 1 . . C
    H11 -0.4269 0.6281 0.7596 0.071 Uiso calc R 1 . . H
    C12 -0.3436(4) 0.6734(3) 0.61991(18) 0.0689(6) Uani d . 1 . . C
    H12 -0.4957 0.6212 0.5861 0.083 Uiso calc R 1 . . H
    C13 -0.1558(4) 0.7472(3) 0.56837(18) 0.0680(6) Uani d . 1 . . C
    C14 0.0694(4) 0.8294(4) 0.61565(19) 0.0737(7) Uani d . 1 . . C
    H14 0.1926 0.8808 0.5787 0.088 Uiso calc R 1 . . H
    C15 0.1084(4) 0.8338(3) 0.71906(18) 0.0615(6) Uani d . 1 . . C
    H15 0.2604 0.8891 0.7522 0.074 Uiso calc R 1 . . H
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Cl1 0.0533(3) 0.0801(4) 0.0606(4) 0.0033(3) -0.0032(2) 0.0077(3)
    F1 0.0939(12) 0.1413(14) 0.0630(9) -0.0002(10) -0.0045(8) 0.0322(9)
    N1 0.0306(8) 0.0529(9) 0.0597(10) 0.0030(7) 0.0049(7) 0.0092(7)
    N4 0.0307(7) 0.0437(8) 0.0570(10) 0.0031(6) 0.0051(6) 0.0043(7)
    N5 0.0349(8) 0.0522(9) 0.0560(10) 0.0027(7) 0.0012(7) 0.0027(7)
    C2 0.0356(9) 0.0411(10) 0.0622(12) 0.0054(8) 0.0092(8) 0.0078(8)
    C3 0.0340(9) 0.0489(11) 0.0577(12) -0.0015(8) 0.0085(8) 0.0068(8)
    C6 0.0412(10) 0.0476(11) 0.0571(12) 0.0097(8) 0.0019(8) 0.0034(9)
    C7 0.0415(10) 0.0581(12) 0.0587(12) 0.0083(9) 0.0117(9) 0.0115(9)
    C8 0.0339(9) 0.0544(11) 0.0639(13) 0.0036(8) 0.0108(8) 0.0107(9)
    C9 0.0290(9) 0.0445(10) 0.0623(12) 0.0054(7) 0.0060(8) 0.0059(8)
    C10 0.0378(10) 0.0435(10) 0.0594(12) 0.0056(8) 0.0055(8) 0.0072(8)
    C11 0.0454(11) 0.0626(13) 0.0639(14) -0.0034(9) 0.0054(9) 0.0103(10)
    C12 0.0533(13) 0.0776(15) 0.0670(15) -0.0029(11) -0.0054(11) 0.0101(12)
    C13 0.0646(14) 0.0801(16) 0.0576(13) 0.0069(12) 0.0011(11) 0.0173(11)
    C14 0.0554(13) 0.0949(18) 0.0712(16) 0.0015(12) 0.0109(11) 0.0290(13)
    C15 0.0396(11) 0.0757(15) 0.0673(14) 0.0003(10) 0.0033(9) 0.0204(11)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cl1 C6 . 1.723(2) ?
    F1 C13 . 1.368(3) ?
    N1 C9 . 1.318(2) ?
    N1 C2 . 1.376(2) ?
    N4 N5 . 1.359(2) ?
    N4 C3 . 1.366(2) ?
    N4 C9 . 1.391(2) ?
    N5 C6 . 1.304(3) ?
    C2 C3 . 1.373(3) ?
    C2 C10 . 1.459(3) ?
    C3 H3 . 0.9300 ?
    C6 C7 . 1.423(3) ?
    C7 C8 . 1.344(3) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.412(3) ?
    C8 H8 . 0.9300 ?
    C10 C15 . 1.391(3) ?
    C10 C11 . 1.398(3) ?
    C11 C12 . 1.375(3) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.365(3) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.369(3) ?
    C14 C15 . 1.373(3) ?
    C14 H14 . 0.9300 ?
    C15 H15 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C9 N1 C2 . . 105.43(15) ?
    N5 N4 C3 . . 126.43(15) ?
    N5 N4 C9 . . 126.37(16) ?
    C3 N4 C9 . . 107.20(16) ?
    C6 N5 N4 . . 113.38(16) ?
    C3 C2 N1 . . 111.03(18) ?
    C3 C2 C10 . . 128.26(17) ?
    N1 C2 C10 . . 120.68(16) ?
    N4 C3 C2 . . 105.47(16) ?
    N4 C3 H3 . . 127.3 ?
    C2 C3 H3 . . 127.3 ?
    N5 C6 C7 . . 126.02(19) ?
    N5 C6 Cl1 . . 115.28(15) ?
    C7 C6 Cl1 . . 118.70(16) ?
    C8 C7 C6 . . 118.90(19) ?
    C8 C7 H7 . . 120.6 ?
    C6 C7 H7 . . 120.6 ?
    C7 C8 C9 . . 118.34(18) ?
    C7 C8 H8 . . 120.8 ?
    C9 C8 H8 . . 120.8 ?
    N1 C9 N4 . . 110.88(16) ?
    N1 C9 C8 . . 132.12(17) ?
    N4 C9 C8 . . 117.00(17) ?
    C15 C10 C11 . . 117.5(2) ?
    C15 C10 C2 . . 122.11(17) ?
    C11 C10 C2 . . 120.36(17) ?
    C12 C11 C10 . . 121.7(2) ?
    C12 C11 H11 . . 119.2 ?
    C10 C11 H11 . . 119.2 ?
    C13 C12 C11 . . 118.0(2) ?
    C13 C12 H12 . . 121.0 ?
    C11 C12 H12 . . 121.0 ?
    C12 C13 F1 . . 118.3(2) ?
    C12 C13 C14 . . 122.9(2) ?
    F1 C13 C14 . . 118.7(2) ?
    C13 C14 C15 . . 118.3(2) ?
    C13 C14 H14 . . 120.9 ?
    C15 C14 H14 . . 120.9 ?
    C14 C15 C10 . . 121.5(2) ?
    C14 C15 H15 . . 119.2 ?
    C10 C15 H15 . . 119.2 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C3 N4 N5 C6 . . . . -179.37(17) ?
    C9 N4 N5 C6 . . . . 0.2(3) ?
    C9 N1 C2 C3 . . . . 0.0(2) ?
    C9 N1 C2 C10 . . . . 178.04(15) ?
    N5 N4 C3 C2 . . . . 179.61(15) ?
    C9 N4 C3 C2 . . . . 0.0(2) ?
    N1 C2 C3 N4 . . . . 0.0(2) ?
    C10 C2 C3 N4 . . . . -177.84(17) ?
    N4 N5 C6 C7 . . . . -0.5(3) ?
    N4 N5 C6 Cl1 . . . . 178.79(11) ?
    N5 C6 C7 C8 . . . . 0.6(3) ?
    Cl1 C6 C7 C8 . . . . -178.69(15) ?
    C6 C7 C8 C9 . . . . -0.3(3) ?
    C2 N1 C9 N4 . . . . 0.0(2) ?
    C2 N1 C9 C8 . . . . -179.5(2) ?
    N5 N4 C9 N1 . . . . -179.61(15) ?
    C3 N4 C9 N1 . . . . 0.0(2) ?
    N5 N4 C9 C8 . . . . 0.0(3) ?
    C3 N4 C9 C8 . . . . 179.64(15) ?
    C7 C8 C9 N1 . . . . 179.57(18) ?
    C7 C8 C9 N4 . . . . 0.1(3) ?
    C3 C2 C10 C15 . . . . -0.3(3) ?
    N1 C2 C10 C15 . . . . -178.01(19) ?
    C3 C2 C10 C11 . . . . 179.5(2) ?
    N1 C2 C10 C11 . . . . 1.8(3) ?
    C15 C10 C11 C12 . . . . 0.8(3) ?
    C2 C10 C11 C12 . . . . -178.99(19) ?
    C10 C11 C12 C13 . . . . 0.4(4) ?
    C11 C12 C13 F1 . . . . -179.6(2) ?
    C11 C12 C13 C14 . . . . -1.6(4) ?
    C12 C13 C14 C15 . . . . 1.4(4) ?
    F1 C13 C14 C15 . . . . 179.4(2) ?
    C13 C14 C15 C10 . . . . -0.1(4) ?
    C11 C10 C15 C14 . . . . -1.0(3) ?
    C2 C10 C15 C14 . . . . 178.79(19) ?
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
    C7 H7 F1 1_556 0.93 2.64 3.470(3) 149 yes
    C8 H8 N1 2_467 0.93 2.68 3.573(2) 161 yes
