#------------------------------------------------------------------------------
#$Date: 2018-01-08 11:57:05 +0200 (Mon, 08 Jan 2018) $
#$Revision: 204919 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/00/02/8000259.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_8000259
loop_
_publ_author_name
'Garrett C. Moraski'
'Allen G. Oliver'
'Lowell D. Markley'
'Sanghyun Cho'
'Scott G. Franzblau'
'Marvin J. Miller'
_publ_section_title
;
 Scaffold-switching: An exploration of 5,6-fused bicyclic heteroaromatics
 systems to afford antituberculosis activity akin to the
 imidazo[1,2-a]pyridine-3-carboxylates
;
_journal_name_full               'Bioorganic & Medicinal Chemistry Letters'
_journal_page_first              3493
_journal_page_last               3498
_journal_paper_doi               10.1016/j.bmcl.2014.05.062
_journal_volume                  24
_journal_year                    2014
_chemical_formula_sum            'C16 H16 N4 O'
_chemical_formula_weight         280.33
_chemical_name_common
;
N-Benzyl-2,6-dimethylimidazo[1,2-b]pyridazine-3-carboxamide
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      11
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_cell_angle_alpha                90.
_cell_angle_beta                 106.2760(10)
_cell_angle_gamma                90.
_cell_formula_units_Z            2
_cell_length_a                   9.3005(8)
_cell_length_b                   6.6121(5)
_cell_length_c                   11.8267(10)
_cell_volume                     698.14(10)
_diffrn_ambient_temperature      120
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_exptl_absorpt_coefficient_mu    0.087
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             296
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1540
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_gt          0.1275
_refine_ls_wR_factor_ref         0.1306
_cod_data_source_file            Bioorg-Med-Chem-Lett-2014-24-3493-3498-2.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               8000259
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,1/2+y,-z
3 -x,-y,-z
4 x,1/2-y,z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O Uani 0.26712(14) 0.25000 1.05522(12) 1.000 0.0269(4) . . . .
N1 N Uani 0.51055(17) 0.25000 0.79346(13) 1.000 0.0201(4) . . . .
N4 N Uani 0.62630(16) 0.25000 0.98657(13) 1.000 0.0168(4) . . . .
N5 N Uani 0.73938(16) 0.25000 1.08855(13) 1.000 0.0193(4) . . . .
N12 N Uani 0.49978(16) 0.25000 1.18313(13) 1.000 0.0206(4) . . . .
C2 C Uani 0.40717(19) 0.25000 0.85507(15) 1.000 0.0187(5) . . . .
C3 C Uani 0.47377(19) 0.25000 0.97569(15) 1.000 0.0177(5) . . . .
C6 C Uani 0.8756(2) 0.25000 1.07619(16) 1.000 0.0210(5) . . . .
C7 C Uani 0.9064(2) 0.25000 0.96462(17) 1.000 0.0238(6) . . . .
C8 C Uani 0.7903(2) 0.25000 0.86417(16) 1.000 0.0227(5) . . . .
C9 C Uani 0.6432(2) 0.25000 0.87411(15) 1.000 0.0185(5) . . . .
C10 C Uani 0.2437(2) 0.25000 0.79171(16) 1.000 0.0240(5) . . . .
C11 C Uani 0.4045(2) 0.25000 1.07439(16) 1.000 0.0181(5) . . . .
C13 C Uani 0.4502(2) 0.25000 1.29012(16) 1.000 0.0229(5) . . . .
C14 C Uani 0.5888(2) 0.25000 1.39403(15) 1.000 0.0236(6) . . . .
C15 C Uani 0.6561(2) 0.0698(3) 1.43920(13) 1.000 0.0449(5) . . . .
C16 C Uani 0.7922(2) 0.0706(4) 1.52619(15) 1.000 0.0628(7) . . . .
C17 C Uani 0.8608(3) 0.25000 1.5683(2) 1.000 0.0582(11) . . . .
C18 C Uani 1.0001(2) 0.25000 1.18869(17) 1.000 0.0280(6) . . . .
H7A H Uiso 1.00690 0.25000 0.96040 1.000 0.0290 . . . .
H8A H Uiso 0.80850 0.25000 0.78900 1.000 0.0270 . . . .
H10A H Uiso 0.18800 0.25000 0.83360 0.500 0.0290 . . . .
H10B H Uiso 0.22060 0.12930 0.74730 0.500 0.0290 . . . .
H10C H Uiso 0.22910 0.25000 0.70570 0.500 0.0290 . . . .
H10D H Uiso 0.19300 0.14580 0.82330 0.500 0.0290 . . . .
H12 H Uiso 0.59970 0.25000 1.18980 1.000 0.0250 . . . .
H13 H Uiso 0.36720 0.11250 1.28610 1.000 0.0270 . . . .
H15A H Uiso 0.60920 -0.05500 1.41070 1.000 0.0540 . . . .
H16A H Uiso 0.83800 -0.05380 1.55680 1.000 0.0750 . . . .
H17A H Uiso 0.95520 0.25000 1.62610 1.000 0.0700 . . . .
H18A H Uiso 0.96900 0.25000 1.25690 1.000 0.0340 . . . .
H18B H Uiso 1.06350 0.12610 1.19270 1.000 0.0340 . . . .
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C9 105.58(15) . . . yes
N5 N4 C3 126.76(15) . . . yes
N5 N4 C9 125.81(15) . . . yes
C3 N4 C9 107.44(15) . . . yes
N4 N5 C6 115.53(15) . . . yes
C11 N12 C13 123.05(16) . . . yes
N1 C2 C3 111.85(16) . . . yes
N1 C2 C10 120.27(15) . . . yes
C3 C2 C10 127.88(17) . . . no
N4 C3 C2 104.22(15) . . . yes
N4 C3 C11 125.82(15) . . . yes
C2 C3 C11 129.97(17) . . . no
N5 C6 C7 123.51(17) . . . yes
N5 C6 C18 115.45(16) . . . yes
C7 C6 C18 121.03(17) . . . no
C6 C7 C8 119.39(18) . . . no
C7 C8 C9 118.62(17) . . . no
N1 C9 N4 110.91(16) . . . yes
N1 C9 C8 131.94(17) . . . yes
N4 C9 C8 117.15(16) . . . yes
O1 C11 N12 123.23(17) . . . yes
O1 C11 C3 120.76(16) . . . yes
N12 C11 C3 116.01(16) . . . yes
C11 N12 H12 118.00 . . . no
C13 N12 H12 119.00 . . . no
N12 C13 C14 107.43(15) . . . yes
C13 C14 C15 120.34(10) . . 4_555 no
C15 C14 C15 119.15(17) . . 4_555 no
C13 C14 C15 120.34(10) . . . no
C14 C15 C16 120.19(19) . . . no
C15 C16 C17 120.4(2) . . . no
C16 C17 C16 119.6(2) . . 4_555 no
C6 C7 H7A 120.00 . . . no
C8 C7 H7A 120.00 . . . no
C7 C8 H8A 121.00 . . . no
C9 C8 H8A 121.00 . . . no
C2 C10 H10A 115.00 . . . no
C2 C10 H10B 109.00 . . . no
C2 C10 H10C 110.00 . . . no
C2 C10 H10D 110.00 . . . no
C2 C10 H10B 109.00 . . 4_555 no
C2 C10 H10D 110.00 . . 4_555 no
H10A C10 H10B 105.00 . . . no
H10A C10 H10C 135.00 . . . no
H10A C10 H10D 46.00 . . . no
H10A C10 H10B 105.00 . . 4_555 no
H10A C10 H10D 46.00 . . 4_555 no
H10B C10 H10C 59.00 . . . no
H10B C10 H10D 64.00 . . . no
H10B C10 H10B 115.00 . . 4_555 no
H10B C10 H10D 139.00 . . 4_555 no
H10C C10 H10D 117.00 . . . no
H10B C10 H10C 59.00 4_555 . . no
H10C C10 H10D 117.00 . . 4_555 no
H10B C10 H10D 139.00 4_555 . . no
H10D C10 H10D 91.00 . . 4_555 no
H10B C10 H10D 64.00 4_555 . 4_555 no
N12 C13 H13 109.00 . . . no
N12 C13 H13 109.00 . . 4_555 no
C14 C13 H13 115.00 . . . no
C14 C13 H13 115.00 . . 4_555 no
H13 C13 H13 100.00 . . 4_555 no
C14 C15 H15A 120.00 . . . no
C16 C15 H15A 120.00 . . . no
C15 C16 H16A 120.00 . . . no
C17 C16 H16A 120.00 . . . no
C16 C17 H17A 120.00 . . . no
C16 C17 H17A 120.00 4_555 . . no
C6 C18 H18A 115.00 . . . no
C6 C18 H18B 110.00 . . . no
C6 C18 H18B 110.00 . . 4_555 no
H18A C18 H18B 106.00 . . . no
H18A C18 H18B 106.00 . . 4_555 no
H18B C18 H18B 110.00 . . 4_555 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.234(2) . . yes
N1 C2 1.359(2) . . yes
N1 C9 1.331(2) . . yes
N4 N5 1.360(2) . . yes
N4 C3 1.388(2) . . yes
N4 C9 1.382(2) . . yes
N5 C6 1.315(2) . . yes
N12 C11 1.342(2) . . yes
N12 C13 1.463(2) . . yes
C2 C3 1.387(2) . . no
C2 C10 1.495(3) . . no
C3 C11 1.483(3) . . no
C6 C7 1.427(3) . . no
C6 C18 1.499(3) . . no
C7 C8 1.363(3) . . no
C8 C9 1.406(3) . . no
N12 H12 0.9100 . . no
C13 C14 1.511(3) . . no
C14 C15 1.382(2) . . no
C14 C15 1.382(2) . 4_555 no
C15 C16 1.390(2) . . no
C16 C17 1.373(3) . . no
C7 H7A 0.9500 . . no
C8 H8A 0.9500 . . no
C10 H10A 0.8100 . . no
C10 H10B 0.9500 . . no
C10 H10C 0.9900 . . no
C10 H10D 0.9700 . . no
C10 H10B 0.9500 . 4_555 no
C10 H10D 0.9700 . 4_555 no
C13 H13 1.1800 . . no
C13 H13 1.1800 . 4_555 no
C15 H15A 0.9500 . . no
C16 H16A 0.9500 . . no
C17 H17A 0.9500 . . no
C18 H18A 0.9300 . . no
C18 H18B 1.0000 . . no
C18 H18B 1.0000 . 4_555 no
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
_geom_hbond_publ_flag
N12 H12 N4 0.9100 2.4800 2.885(2) 107.00 . yes
N12 H12 N5 0.9100 2.0000 2.759(2) 140.00 . yes
C7 H7A O1 0.9500 2.3700 3.223(2) 150.00 1_655 yes
C10 H10A O1 0.8100 2.5200 3.063(2) 126.00 . yes
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
C9 N1 C2 C3 0.00(1) . . . . no
C9 N1 C2 C10 180.00(1) . . . . no
C2 N1 C9 N4 0.00(1) . . . . no
C2 N1 C9 C8 180.00(1) . . . . no
C3 N4 N5 C6 180.00(1) . . . . no
C9 N4 N5 C6 0.00(1) . . . . no
N5 N4 C3 C2 -180.00(1) . . . . no
N5 N4 C3 C11 0.00(1) . . . . no
C9 N4 C3 C2 0.00(1) . . . . no
C9 N4 C3 C11 180.00(1) . . . . no
N5 N4 C9 N1 180.00(1) . . . . no
N5 N4 C9 C8 0.00(1) . . . . no
C3 N4 C9 N1 0.00(1) . . . . no
C3 N4 C9 C8 180.00(1) . . . . no
N4 N5 C6 C7 0.00(1) . . . . no
N4 N5 C6 C18 180.00(1) . . . . no
C13 N12 C11 O1 0.00(1) . . . . no
C13 N12 C11 C3 180.00(1) . . . . no
C11 N12 C13 C14 180.00(1) . . . . no
N1 C2 C3 N4 0.00(1) . . . . no
N1 C2 C3 C11 -180.00(1) . . . . no
C10 C2 C3 N4 -180.00(1) . . . . no
C10 C2 C3 C11 0.00(1) . . . . no
N4 C3 C11 O1 180.00(1) . . . . no
N4 C3 C11 N12 0.00(1) . . . . no
C2 C3 C11 O1 0.00(1) . . . . no
C2 C3 C11 N12 180.00(1) . . . . no
N5 C6 C7 C8 0.00(1) . . . . no
C18 C6 C7 C8 180.00(1) . . . . no
C6 C7 C8 C9 0.00(1) . . . . no
C7 C8 C9 N1 180.00(1) . . . . no
C7 C8 C9 N4 0.00(1) . . . . no
N12 C13 C14 C15 -87.54(16) . . . . no
C13 C14 C15 C16 173.03(17) . . . . no
C15 C14 C15 C16 -2.1(3) 4_555 . . . no
C14 C15 C16 C17 0.2(3) . . . . no
C15 C16 C17 C16 1.7(3) . . . 4_555 no
