#------------------------------------------------------------------------------
#$Date: 2016-03-23 00:10:58 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179097 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/59/4305926.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_4305926
loop_
_publ_author_name
'Rik Rani Koner'
'Manabendra Ray'
_publ_contact_author_address
;Depertment of Chemistry
IIT - Guwahati
North-Guwahati - 781039
;
_publ_contact_author_email       manabray@iitg.ernet.in
_publ_contact_author_fax         913612690762
_publ_contact_author_name        'Dr.Manabendra Ray'
_publ_contact_author_phone       913612582310
_publ_section_title
;
CuII-Mediated Synthesis of a New Fluorescent Pyrido[1,2-a]quinoxalin-11-ium
Derivative
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              9122
_journal_page_last               9124
_journal_paper_doi               10.1021/ic8008464
_journal_volume                  47
_journal_year                    2008
_chemical_compound_source        Synthesis
_chemical_formula_sum            'C13 H10 N4 O S'
_chemical_formula_weight         270.31
_chemical_name_common            ORGSCN
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.728(6)
_cell_angle_beta                 90.896(7)
_cell_angle_gamma                108.176(6)
_cell_formula_units_Z            4
_cell_length_a                   9.3055(9)
_cell_length_b                   11.6353(11)
_cell_length_c                   12.8604(13)
_cell_measurement_reflns_used    2835
_cell_measurement_temperature    296(2)
_cell_volume                     1258.4(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13215
_diffrn_reflns_theta_full        28.80
_diffrn_reflns_theta_max         28.80
_diffrn_reflns_theta_min         3.87
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.254
_exptl_crystal_colour            'dark orange'
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             560
_exptl_crystal_recrystallization_method 'Slow evaporation of methanol'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         6383
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.1137
_refine_ls_R_factor_gt           0.0728
_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)+(0.0900P)²+0.6781P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1949
_refine_ls_wR_factor_ref         0.2211
_reflns_number_gt                3732
_reflns_number_total             6383
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic8008464_si_002_1.cif
_cod_data_source_block           trial
_cod_database_code               4305926
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
S1 S 0.68003(13) 0.26246(11) 0.17848(9) 0.0905(4) Uani 1 1 d . . .
S2 S 0.73238(17) 0.79614(11) 0.73298(12) 0.1124(5) Uani 1 1 d . . .
N2 N 0.3456(2) 0.23170(18) 0.87805(17) 0.0445(5) Uani 1 1 d . . .
C12 C 0.4672(3) 0.3421(2) 0.87764(19) 0.0405(5) Uani 1 1 d . . .
C11 C 0.5972(3) 0.3912(2) 0.95128(19) 0.0421(5) Uani 1 1 d . . .
H25 H 0.6078 0.3515 1.0028 0.050 Uiso 1 1 calc R . .
C7 C 0.4488(3) 0.3997(2) 0.7972(2) 0.0449(5) Uani 1 1 d . . .
C9 C 0.6943(3) 0.5589(2) 0.8690(2) 0.0486(6) Uani 1 1 d . . .
H27 H 0.7706 0.6318 0.8666 0.058 Uiso 1 1 calc R . .
C10 C 0.7124(3) 0.5006(2) 0.9483(2) 0.0447(5) Uani 1 1 d . . .
N3 N 0.3239(3) 0.3535(2) 0.72047(18) 0.0559(6) Uani 1 1 d . . .
C8 C 0.5666(3) 0.5096(2) 0.7962(2) 0.0501(6) Uani 1 1 d . . .
H24 H 0.5571 0.5495 0.7446 0.060 Uiso 1 1 calc R . .
N2A N 0.3035(3) 0.6717(2) 0.40406(18) 0.0545(6) Uani 1 1 d . . .
C5 C 0.2202(3) 0.1869(2) 0.8013(2) 0.0519(6) Uani 1 1 d . . .
C14A C 0.8226(4) 0.2583(3) 0.1078(3) 0.0644(8) Uani 1 1 d . . .
N4A N 0.9229(4) 0.2553(3) 0.0563(3) 0.0921(10) Uani 1 1 d . . .
C12A C 0.3352(3) 0.7632(3) 0.3478(2) 0.0520(6) Uani 1 1 d . . .
C7A C 0.2228(4) 0.7437(3) 0.2630(2) 0.0621(8) Uani 1 1 d . . .
C11A C 0.4703(4) 0.8659(3) 0.3717(2) 0.0583(7) Uani 1 1 d . . .
H3 H 0.5426 0.8778 0.4280 0.070 Uiso 1 1 calc R . .
C10A C 0.4968(4) 0.9509(3) 0.3109(3) 0.0637(8) Uani 1 1 d . . .
C9A C 0.3860(5) 0.9296(4) 0.2250(3) 0.0728(9) Uani 1 1 d . . .
H5 H 0.4038 0.9848 0.1832 0.087 Uiso 1 1 calc R . .
C8A C 0.2549(4) 0.8307(4) 0.2024(3) 0.0729(9) Uani 1 1 d . . .
H8 H 0.1839 0.8195 0.1456 0.088 Uiso 1 1 calc R . .
C5A C 0.1695(4) 0.5711(3) 0.3753(3) 0.0639(8) Uani 1 1 d . . .
C1A C 0.4067(4) 0.6806(3) 0.4862(2) 0.0669(8) Uani 1 1 d . . .
H15 H 0.4976 0.7486 0.5059 0.080 Uiso 1 1 calc R . .
N3A N 0.0884(3) 0.6469(3) 0.2358(2) 0.0719(8) Uani 1 1 d . . .
C4A C 0.1432(5) 0.4776(4) 0.4281(3) 0.0828(10) Uani 1 1 d . . .
H12 H 0.0545 0.4076 0.4070 0.099 Uiso 1 1 calc R . .
C6A C 0.0648(4) 0.5653(4) 0.2913(3) 0.0779(10) Uani 1 1 d . . .
H10 H -0.0274 0.4988 0.2741 0.093 Uiso 1 1 calc R . .
C2A C 0.3776(5) 0.5918(4) 0.5387(3) 0.0794(10) Uani 1 1 d . . .
H14 H 0.4476 0.6007 0.5953 0.095 Uiso 1 1 calc R . .
C3A C 0.2454(5) 0.4878(4) 0.5095(3) 0.0852(11) Uani 1 1 d . . .
H13 H 0.2270 0.4262 0.5449 0.102 Uiso 1 1 calc R . .
C13A C 0.7693(4) 0.8412(4) 0.6369(3) 0.0840(12) Uani 1 1 d . . .
N5A N 0.7982(4) 0.8951(5) 0.5651(3) 0.1179(14) Uani 1 1 d . . .
N1A N 0.6263(4) 1.0515(3) 0.3325(3) 0.0825(8) Uani 1 1 d . . .
H3A H 0.6941 1.0641 0.3845 0.099 Uiso 1 1 calc R . .
H3B H 0.6409 1.1030 0.2943 0.099 Uiso 1 1 calc R . .
C1 C 0.3511(3) 0.1707(3) 0.9537(2) 0.0557(7) Uani 1 1 d . . .
H28 H 0.4355 0.2020 1.0060 0.067 Uiso 1 1 calc R . .
C6 C 0.2172(3) 0.2516(3) 0.7240(2) 0.0596(7) Uani 1 1 d . . .
H32 H 0.1327 0.2189 0.6718 0.071 Uiso 1 1 calc R . .
C4 C 0.1013(3) 0.0781(3) 0.8024(3) 0.0662(8) Uani 1 1 d . . .
H31 H 0.0161 0.0470 0.7509 0.079 Uiso 1 1 calc R . .
C2 C 0.2351(4) 0.0648(3) 0.9537(3) 0.0698(8) Uani 1 1 d . . .
H29 H 0.2411 0.0240 1.0052 0.084 Uiso 1 1 calc R . .
C3 C 0.1076(4) 0.0175(3) 0.8768(3) 0.0751(9) Uani 1 1 d . . .
H30 H 0.0279 -0.0547 0.8765 0.090 Uiso 1 1 calc R . .
N1 N 0.8390(3) 0.5533(2) 1.0220(2) 0.0602(6) Uani 1 1 d . . .
H5A H 0.8493 0.5194 1.0716 0.072 Uiso 1 1 calc R . .
H5B H 0.9090 0.6207 1.0190 0.072 Uiso 1 1 calc R . .
O1A O 0.8928(4) 0.1254(4) 0.4983(3) 0.1377(14) Uani 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'
S S 0.1246 0.1234 '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
C1 N2 C5 119.9(2) . . ?
C1 N2 C12 121.1(2) . . ?
C5 N2 C12 119.0(2) . . ?
C11 C12 C7 121.3(2) . . ?
C11 C12 N2 122.1(2) . . ?
C7 C12 N2 116.6(2) . . ?
C12 C11 C10 119.9(2) . . ?
C12 C11 H25 120.0 . . ?
C10 C11 H25 120.0 . . ?
N3 C7 C8 118.6(2) . . ?
N3 C7 C12 123.8(2) . . ?
C8 C7 C12 117.6(2) . . ?
C8 C9 C10 120.7(2) . . ?
C8 C9 H27 119.6 . . ?
C10 C9 H27 119.6 . . ?
N1 C10 C11 121.2(2) . . ?
N1 C10 C9 119.7(2) . . ?
C11 C10 C9 119.1(2) . . ?
C6 N3 C7 116.8(2) . . ?
C9 C8 C7 121.4(2) . . ?
C9 C8 H24 119.3 . . ?
C7 C8 H24 119.3 . . ?
C5A N2A C1A 119.3(3) . . ?
C5A N2A C12A 119.9(2) . . ?
C1A N2A C12A 120.8(3) . . ?
N2 C5 C4 118.5(3) . . ?
N2 C5 C6 118.8(2) . . ?
C4 C5 C6 122.7(3) . . ?
N4A C14A S1 179.1(3) . . ?
C11A C12A N2A 122.6(2) . . ?
C11A C12A C7A 121.1(3) . . ?
N2A C12A C7A 116.3(3) . . ?
N3A C7A C8A 118.3(3) . . ?
N3A C7A C12A 124.4(3) . . ?
C8A C7A C12A 117.3(3) . . ?
C12A C11A C10A 119.8(3) . . ?
C12A C11A H3 120.1 . . ?
C10A C11A H3 120.1 . . ?
N1A C10A C11A 121.1(3) . . ?
N1A C10A C9A 120.0(3) . . ?
C11A C10A C9A 118.9(3) . . ?
C8A C9A C10A 121.2(3) . . ?
C8A C9A H5 119.4 . . ?
C10A C9A H5 119.4 . . ?
C9A C8A C7A 121.6(3) . . ?
C9A C8A H8 119.2 . . ?
C7A C8A H8 119.2 . . ?
N2A C5A C4A 119.2(3) . . ?
N2A C5A C6A 118.0(3) . . ?
C4A C5A C6A 122.8(3) . . ?
C2A C1A N2A 120.8(3) . . ?
C2A C1A H15 119.6 . . ?
N2A C1A H15 119.6 . . ?
C6A N3A C7A 116.6(3) . . ?
C3A C4A C5A 120.9(4) . . ?
C3A C4A H12 119.5 . . ?
C5A C4A H12 119.5 . . ?
N3A C6A C5A 124.8(3) . . ?
N3A C6A H10 117.6 . . ?
C5A C6A H10 117.6 . . ?
C1A C2A C3A 121.1(4) . . ?
C1A C2A H14 119.5 . . ?
C3A C2A H14 119.5 . . ?
C4A C3A C2A 118.7(4) . . ?
C4A C3A H13 120.7 . . ?
C2A C3A H13 120.7 . . ?
N5A C13A S2 171.0(4) . . ?
C10A N1A H3A 120.0 . . ?
C10A N1A H3B 120.0 . . ?
H3A N1A H3B 120.0 . . ?
C2 C1 N2 121.0(3) . . ?
C2 C1 H28 119.5 . . ?
N2 C1 H28 119.5 . . ?
N3 C6 C5 124.9(3) . . ?
N3 C6 H32 117.6 . . ?
C5 C6 H32 117.6 . . ?
C3 C4 C5 121.5(3) . . ?
C3 C4 H31 119.3 . . ?
C5 C4 H31 119.3 . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H29 119.9 . . ?
C3 C2 H29 119.9 . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H30 120.5 . . ?
C2 C3 H30 120.5 . . ?
C10 N1 H5A 120.0 . . ?
C10 N1 H5B 120.0 . . ?
H5A N1 H5B 120.0 . . ?
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
S1 C14A 1.625(4) . ?
S2 C13A 1.481(5) . ?
N2 C1 1.369(3) . ?
N2 C5 1.377(3) . ?
N2 C12 1.424(3) . ?
C12 C11 1.381(3) . ?
C12 C7 1.420(3) . ?
C11 C10 1.396(3) . ?
C11 H25 0.9300 . ?
C7 N3 1.372(3) . ?
C7 C8 1.404(4) . ?
C9 C8 1.361(4) . ?
C9 C10 1.412(4) . ?
C9 H27 0.9300 . ?
C10 N1 1.357(3) . ?
N3 C6 1.300(4) . ?
C8 H24 0.9300 . ?
N2A C5A 1.373(4) . ?
N2A C1A 1.375(4) . ?
N2A C12A 1.414(4) . ?
C5 C4 1.402(4) . ?
C5 C6 1.414(4) . ?
C14A N4A 1.156(4) . ?
C12A C11A 1.394(4) . ?
C12A C7A 1.417(4) . ?
C7A N3A 1.355(4) . ?
C7A C8A 1.411(5) . ?
C11A C10A 1.396(4) . ?
C11A H3 0.9300 . ?
C10A N1A 1.350(5) . ?
C10A C9A 1.411(5) . ?
C9A C8A 1.348(5) . ?
C9A H5 0.9300 . ?
C8A H8 0.9300 . ?
C5A C4A 1.404(5) . ?
C5A C6A 1.417(5) . ?
C1A C2A 1.353(5) . ?
C1A H15 0.9300 . ?
N3A C6A 1.313(5) . ?
C4A C3A 1.357(6) . ?
C4A H12 0.9300 . ?
C6A H10 0.9300 . ?
C2A C3A 1.383(6) . ?
C2A H14 0.9300 . ?
C3A H13 0.9300 . ?
C13A N5A 1.247(6) . ?
N1A H3A 0.8600 . ?
N1A H3B 0.8600 . ?
C1 C2 1.362(4) . ?
C1 H28 0.9300 . ?
C6 H32 0.9300 . ?
C4 C3 1.353(5) . ?
C4 H31 0.9300 . ?
C2 C3 1.389(5) . ?
C2 H29 0.9300 . ?
C3 H30 0.9300 . ?
N1 H5A 0.8600 . ?
N1 H5B 0.8600 . ?
