#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/53/2005387.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_2005387
loop_
_publ_author_name
'Fun, H.-K.'
'Sivakumar, K.'
'Chua, S.-O.'
'Ooi, M.-F.'
'Anwair, M. A. S.'
'Gan, E.-K.'
'Jackson, W. R.'
_publ_section_title
;
 Substituted Imidazonaphthyridine Derivatives. I. C₁₉H₁₄F₃N₃,
 C₁₈H₁₀F₅N₃, C₁₈H₁₁ClF₃N₃ and C₁₈H₁₁BrF₃N₃
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2231
_journal_page_last               2236
_journal_paper_doi               10.1107/S010827019600371X
_journal_volume                  52
_journal_year                    1996
_chemical_formula_sum            'C19 H14 F3 N3'
_chemical_formula_weight         341.33
_chemical_name_systematic
;
6-methyl-2-(4-methylphenyl)-8-trifluoromethylimidazo[1,2-a][1,8]
naphthyridine.
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                68.90(1)
_cell_angle_beta                 69.39(1)
_cell_angle_gamma                72.67(1)
_cell_formula_units_Z            2
_cell_length_a                   9.092(1)
_cell_length_b                   9.849(1)
_cell_length_c                   10.428(1)
_cell_measurement_reflns_used    36
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      10
_cell_volume                     799.62(16)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  'SHELXL93, PARST (Nardelli, 1983)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution
'SHELXTL/PC (Sheldrick, 1990) (direct methods)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4 diffractometer'
_diffrn_measurement_method       'θ/2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0123
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3324
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.18
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_description       'Thick plate'
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.24
_refine_ls_extinction_coef       0.011(4)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.045
_refine_ls_goodness_of_fit_obs   1.177
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         2760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_restrained_S_obs      1.177
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_obs          0.0457
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0922P)²+0.0191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1446
_refine_ls_wR_factor_obs         0.1352
_reflns_number_observed          1981
_reflns_number_total             2760
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            mu1237.cif
_cod_data_source_block           I
_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 

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.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0922P)^2^+0.0191P] where P=(Fo^2^+2Fc^2^)/3' 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^(Fo^2^)+(0.0922P)^2^+0.0191P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        799.62(14)
_cod_database_code               2005387
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_type_symbol
N1 1 0.2779(2) 1.0662(2) 0.9372(2) 0.0543(5) Uani d N
N2 1 0.2702(2) 0.9060(2) 0.5837(2) 0.0517(4) Uani d N
N3 1 0.2883(2) 0.9770(2) 0.7651(2) 0.0463(4) Uani d N
C1 1 0.3670(3) 0.9782(2) 0.8579(2) 0.0501(5) Uani d C
C2 1 0.5230(3) 0.8911(2) 0.8528(2) 0.0595(6) Uani d C
C3 1 0.5944(3) 0.8118(2) 0.7586(2) 0.0584(5) Uani d C
C4 1 0.5153(2) 0.8123(2) 0.6606(2) 0.0498(5) Uani d C
C5 1 0.5853(3) 0.7353(2) 0.5564(2) 0.0562(5) Uani d C
C6 1 0.4936(3) 0.7453(2) 0.4707(2) 0.0610(6) Uani d C
C7 1 0.3403(3) 0.8290(2) 0.4887(2) 0.0554(5) Uani d C
C8 1 0.3590(2) 0.8962(2) 0.6659(2) 0.0471(5) Uani d C
C9 1 0.1426(2) 1.0696(2) 0.7910(2) 0.0490(5) Uani d C
C10 1 0.1373(2) 1.1246(2) 0.8967(2) 0.0484(5) Uani d C
C11 1 0.0100(2) 1.2301(2) 0.9631(2) 0.0498(5) Uani d C
C12 1 -0.1263(3) 1.3027(3) 0.9151(3) 0.0646(6) Uani d C
C13 1 -0.2425(3) 1.4026(3) 0.9780(3) 0.0694(6) Uani d C
C14 1 -0.2314(3) 1.4365(2) 1.0919(2) 0.0590(6) Uani d C
C15 1 -0.0972(3) 1.3630(2) 1.1404(2) 0.0627(6) Uani d C
C16 1 0.0204(3) 1.2621(2) 1.0782(2) 0.0576(5) Uani d C
C17 1 0.7519(4) 0.6446(4) 0.5398(3) 0.0764(7) Uani d C
C18 1 0.2345(3) 0.8319(3) 0.4049(3) 0.0710(7) Uani d C
C19 1 -0.3580(4) 1.5474(3) 1.1594(3) 0.0803(8) Uani d C
F1 1 0.1459(2) 0.9639(2) 0.3628(2) 0.0990(6) Uani d F
F2 1 0.3170(2) 0.7939(2) 0.2863(2) 0.1213(7) Uani d F
F3 1 0.1331(3) 0.7415(2) 0.4791(2) 0.1314(8) Uani d F
H2 1 0.5826(29) 0.8960(24) 0.9148(24) 0.072(7) Uiso d H
H3 1 0.7067(29) 0.7551(24) 0.7501(23) 0.067(6) Uiso d H
H6 1 0.5325(26) 0.6988(23) 0.4010(24) 0.059(6) Uiso d H
H9 1 0.0613(27) 1.0838(22) 0.7453(22) 0.059(6) Uiso d H
H12 1 -0.1339(34) 1.2805(29) 0.8413(29) 0.091(8) Uiso d H
H13 1 -0.3421(36) 1.4483(28) 0.9475(29) 0.093(8) Uiso d H
H15 1 -0.0888(32) 1.3802(27) 1.2260(28) 0.089(8) Uiso d H
H16 1 0.1070(31) 1.2160(25) 1.1136(24) 0.067(7) Uiso d H
H17A 1 0.7872(37) 0.6101(33) 0.4606(36) 0.104(10) Uiso d H
H17B 1 0.7619(41) 0.5540(37) 0.6122(36) 0.119(12) Uiso d H
H17C 1 0.8270(45) 0.7004(36) 0.5274(35) 0.124(12) Uiso d H
H19A 1 -0.3294(47) 1.6415(42) 1.1374(38) 0.143(13) Uiso d H
H19B 1 -0.4624(61) 1.5494(46) 1.1507(48) 0.177(18) Uiso d H
H19C 1 -0.3914(48) 1.5022(38) 1.2568(41) 0.138(13) Uiso d H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C10 106.17(15)
C7 N2 C8 115.0(2)
C9 N3 C8 130.8(2)
C9 N3 C1 106.8(2)
C8 N3 C1 122.4(2)
N1 C1 N3 110.8(2)
N1 C1 C2 130.6(2)
N3 C1 C2 118.6(2)
C3 C2 C1 120.5(2)
C2 C3 C4 121.3(2)
C5 C4 C8 116.9(2)
C5 C4 C3 124.1(2)
C8 C4 C3 119.0(2)
C6 C5 C4 117.4(2)
C6 C5 C17 121.3(2)
C4 C5 C17 121.3(2)
C7 C6 C5 120.1(2)
N2 C7 C6 124.7(2)
N2 C7 C18 114.3(2)
C6 C7 C18 120.9(2)
N2 C8 N3 115.9(2)
N2 C8 C4 125.9(2)
N3 C8 C4 118.2(2)
N3 C9 C10 106.2(2)
C9 C10 N1 110.0(2)
C9 C10 C11 129.1(2)
N1 C10 C11 120.9(2)
C16 C11 C12 117.0(2)
C16 C11 C10 120.6(2)
C12 C11 C10 122.4(2)
C13 C12 C11 121.1(2)
C12 C13 C14 122.0(2)
C15 C14 C13 116.7(2)
C15 C14 C19 121.4(2)
C13 C14 C19 121.9(3)
C16 C15 C14 121.9(2)
C15 C16 C11 121.3(2)
F3 C18 F2 107.2(2)
F3 C18 F1 105.8(2)
F2 C18 F1 105.0(2)
F3 C18 C7 112.1(2)
F2 C18 C7 112.4(2)
F1 C18 C7 113.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.311(3)
N1 C10 1.382(3)
N2 C7 1.331(3)
N2 C8 1.333(2)
N3 C9 1.366(3)
N3 C8 1.392(2)
N3 C1 1.397(2)
C1 C2 1.416(3)
C2 C3 1.341(3)
C3 C4 1.440(3)
C4 C5 1.407(3)
C4 C8 1.408(3)
C5 C6 1.383(3)
C5 C17 1.498(3)
C6 C7 1.378(3)
C7 C18 1.499(3)
C9 C10 1.374(3)
C10 C11 1.461(3)
C11 C16 1.386(3)
C11 C12 1.396(3)
C12 C13 1.368(3)
C13 C14 1.386(3)
C14 C15 1.382(3)
C14 C19 1.500(4)
C15 C16 1.376(3)
C18 F3 1.316(3)
C18 F2 1.321(3)
C18 F1 1.322(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21138139
