#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/62/1506295.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_1506295
loop_
_publ_author_name
'Shibahara, Fumitoshi'
'Kitagawa, Asumi'
'Yamaguchi, Eiji'
'Murai, Toshiaki'
_publ_section_title
;
 Synthesis of 2-azaindolizines by using an iodine-mediated oxidative
 desulfurization promoted cyclization of N-2-pyridylmethyl thioamides and
 an investigation of their photophysical properties.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              5621
_journal_page_last               5624
_journal_paper_doi               10.1021/ol0623623
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C12 H9 N3 '
_chemical_formula_sum            'C12 H9 N3'
_chemical_formula_weight         195.22
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1126(6)
_cell_length_b                   13.096(2)
_cell_length_c                   14.347(2)
_cell_measurement_reflns_used    2109
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.4
_cell_volume                     960.6(2)
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_collection       CRYSTALCLEAR
_computing_data_reduction        'teXsan Ver. 2.0'
_computing_publication_material  'teXsan Ver. 2.0'
_computing_structure_refinement  'teXsan Ver. 2.0'
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 14.62
_diffrn_measured_fraction_theta_full 0.9954
_diffrn_measured_fraction_theta_max 0.9954
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.055
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7918
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             408.00
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.22
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  6572 Friedel Pairs'
_refine_ls_abs_structure_Flack   4.6(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1403
_refine_ls_R_factor_gt           0.0710
_refine_ls_shift/su_max          0.0031
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.05000(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1425
_reflns_number_gt                917
_reflns_number_total             1403
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ol0623623si20060926_103257.cif
_cod_data_source_block           '_AK75p'
_cod_original_sg_symbol_H-M      'P 21 21 21   '
_cod_original_formula_sum        'C12 H9 N3 '
_cod_database_code               1506295
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,-y,1/2+z
1/2+x,1/2-y,-z
-x,1/2+y,1/2-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
N(1) N 0.4524(6) 0.0813(2) 0.2221(2) 0.0514(9) Uani 1.00 1 d
N(2) N 0.6014(6) 0.0379(2) 0.0812(2) 0.0400(8) Uani 1.00 1 d
N(3) N 0.2330(6) -0.1324(2) 0.0800(2) 0.0495(9) Uani 1.00 1 d
C(1) C 0.6480(8) 0.1457(3) 0.1977(3) 0.057(1) Uani 1.00 1 d
C(2) C 0.4246(7) 0.0156(3) 0.1515(2) 0.0398(9) Uani 1.00 1 d
C(3) C 0.6479(7) -0.0071(3) -0.0043(3) 0.0458(10) Uani 1.00 1 d
C(4) C 0.8428(8) 0.0295(3) -0.0578(3) 0.056(1) Uani 1.00 1 d
C(5) C 0.9982(8) 0.1137(3) -0.0299(3) 0.060(1) Uani 1.00 1 d
C(6) C 0.9484(8) 0.1600(3) 0.0522(3) 0.057(1) Uani 1.00 1 d
C(7) C 0.7489(8) 0.1221(3) 0.1103(3) 0.047(1) Uani 1.00 1 d
C(8) C 0.2357(7) -0.0668(3) 0.1514(2) 0.0374(9) Uani 1.00 1 d
C(9) C 0.0611(8) -0.0747(3) 0.2268(2) 0.049(1) Uani 1.00 1 d
C(10) C -0.1202(8) -0.1526(3) 0.2270(3) 0.053(1) Uani 1.00 1 d
C(11) C -0.1255(8) -0.2203(3) 0.1536(3) 0.054(1) Uani 1.00 1 d
C(12) C 0.0527(8) -0.2072(3) 0.0831(3) 0.055(1) Uani 1.00 1 d
H(1) H 0.7156 0.2022 0.2343 0.0722 Uiso 1.00 1 calc
H(2) H 0.5345 -0.0629 -0.0257 0.0597 Uiso 1.00 1 calc
H(3) H 0.8768 -0.0036 -0.1186 0.0726 Uiso 1.00 1 calc
H(4) H 1.1398 0.1382 -0.0698 0.0783 Uiso 1.00 1 calc
H(5) H 1.0509 0.2199 0.0746 0.0690 Uiso 1.00 1 calc
H(6) H 0.0666 -0.0262 0.2779 0.0639 Uiso 1.00 1 calc
H(7) H -0.2461 -0.1586 0.2762 0.0666 Uiso 1.00 1 calc
H(8) H -0.2518 -0.2760 0.1503 0.0635 Uiso 1.00 1 calc
H(9) H 0.0515 -0.2557 0.0333 0.0669 Uiso 1.00 1 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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
C(1) N(1) C(2) 106.4(3) yes
C(2) N(2) C(3) 132.0(3) yes
C(2) N(2) C(7) 107.4(3) yes
C(3) N(2) C(7) 120.6(3) yes
C(8) N(3) C(12) 116.7(3) yes
N(1) C(1) C(7) 111.6(4) yes
N(1) C(1) H(1) 126.7 no
C(7) C(1) H(1) 121.7 no
N(1) C(2) N(2) 110.3(3) yes
N(1) C(2) C(8) 123.4(3) yes
N(2) C(2) C(8) 126.2(3) yes
N(2) C(3) C(4) 118.8(3) yes
N(2) C(3) H(2) 119.5 no
C(4) C(3) H(2) 121.6 no
C(3) C(4) C(5) 122.1(4) yes
C(3) C(4) H(3) 118.5 no
C(5) C(4) H(3) 119.4 no
C(4) C(5) C(6) 119.4(4) yes
C(4) C(5) H(4) 120.4 no
C(6) C(5) H(4) 120.2 no
C(5) C(6) C(7) 119.7(4) yes
C(5) C(6) H(5) 122.4 no
C(7) C(6) H(5) 117.8 no
N(2) C(7) C(1) 104.2(3) yes
N(2) C(7) C(6) 119.4(3) yes
C(1) C(7) C(6) 136.5(4) yes
N(3) C(8) C(2) 119.1(3) yes
N(3) C(8) C(9) 122.4(3) yes
C(2) C(8) C(9) 118.5(3) yes
C(8) C(9) C(10) 118.8(4) yes
C(8) C(9) H(6) 121.0 no
C(10) C(9) H(6) 120.2 no
C(9) C(10) C(11) 119.3(4) yes
C(9) C(10) H(7) 120.9 no
C(11) C(10) H(7) 119.8 no
C(10) C(11) C(12) 118.0(4) yes
C(10) C(11) H(8) 122.1 no
C(12) C(11) H(8) 119.8 no
N(3) C(12) C(11) 124.8(4) yes
N(3) C(12) H(9) 117.6 no
C(11) C(12) H(9) 117.6 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N(1) C(1) 1.355(5) yes
N(1) C(2) 1.337(4) yes
N(2) C(2) 1.385(4) yes
N(2) C(3) 1.381(4) yes
N(2) C(7) 1.401(4) yes
N(3) C(8) 1.337(4) yes
N(3) C(12) 1.345(4) yes
C(1) C(7) 1.390(5) yes
C(1) H(1) 0.971 no
C(2) C(8) 1.449(4) yes
C(3) C(4) 1.345(5) yes
C(3) H(2) 0.982 no
C(4) C(5) 1.417(5) yes
C(4) H(3) 0.990 no
C(5) C(6) 1.349(6) yes
C(5) H(4) 0.977 no
C(6) C(7) 1.408(5) yes
C(6) H(5) 0.997 no
C(8) C(9) 1.406(5) yes
C(9) C(10) 1.378(5) yes
C(9) H(6) 0.970 no
C(10) C(11) 1.377(5) yes
C(10) H(7) 0.959 no
C(11) C(12) 1.372(5) yes
C(11) H(8) 0.975 no
C(12) H(9) 0.956 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
N(1) C(11) 3.567(5) 4_555
N(2) C(9) 3.473(4) 1_655
N(2) C(10) 3.553(4) 1_655
N(3) C(4) 3.519(5) 1_455
N(3) C(12) 3.543(5) 3_545
C(2) C(10) 3.383(5) 1_655
C(2) C(6) 3.396(5) 1_455
C(3) C(12) 3.567(6) 1_655
C(7) C(9) 3.462(5) 1_655
C(7) C(8) 3.559(5) 1_655
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_publ_flag
N(1) C(1) C(7) N(2) 0.1(4) yes
N(1) C(1) C(7) C(6) -178.8(4) yes
N(1) C(2) N(2) C(3) -179.9(3) yes
N(1) C(2) N(2) C(7) 0.4(4) yes
N(1) C(2) C(8) N(3) -176.0(3) yes
N(1) C(2) C(8) C(9) 4.1(5) yes
N(2) C(2) N(1) C(1) -0.3(4) yes
N(2) C(2) C(8) N(3) 3.4(5) yes
N(2) C(2) C(8) C(9) -176.6(3) yes
N(2) C(3) C(4) C(5) -1.2(5) yes
N(2) C(7) C(6) C(5) -1.2(5) yes
N(3) C(8) C(9) C(10) -0.3(5) yes
N(3) C(12) C(11) C(10) -0.3(6) yes
C(1) N(1) C(2) C(8) 179.2(3) yes
C(1) C(7) N(2) C(2) -0.3(4) yes
C(1) C(7) N(2) C(3) 179.9(3) yes
C(1) C(7) C(6) C(5) 177.6(4) yes
C(2) N(1) C(1) C(7) 0.1(4) yes
C(2) N(2) C(3) C(4) -177.6(3) yes
C(2) N(2) C(7) C(6) 178.8(3) yes
C(2) C(8) N(3) C(12) -179.6(3) yes
C(2) C(8) C(9) C(10) 179.6(3) yes
C(3) N(2) C(2) C(8) 0.7(6) yes
C(3) N(2) C(7) C(6) -0.9(5) yes
C(3) C(4) C(5) C(6) -0.9(6) yes
C(4) C(3) N(2) C(7) 2.1(5) yes
C(4) C(5) C(6) C(7) 2.0(6) yes
C(7) N(2) C(2) C(8) -179.0(3) yes
C(8) N(3) C(12) C(11) 0.0(5) yes
C(8) C(9) C(10) C(11) 0.0(5) yes
C(9) C(8) N(3) C(12) 0.3(5) yes
C(9) C(10) C(11) C(12) 0.3(6) yes
C(9) C(10) C(11) C(12) 0.3(6) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10511994
2 PubChem 12634289
