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#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/15/2221548.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_2221548
loop_
_publ_author_name
'Stefańska, Anita'
'Zarzeczańska, Dorota'
'Ossowski, Tadeusz'
'Sikorski, Artur'
_publ_section_title
;
 Pyrazino[2,3-b]indolizine-10-carbonitrile
;
_journal_coeditor_code           WW2144
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o772
_journal_page_last               o773
_journal_paper_doi               10.1107/S1600536809008939
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H6 N4'
_chemical_formula_moiety         'C11 H6 N4'
_chemical_formula_sum            'C11 H6 N4'
_chemical_formula_weight         194.20
_chemical_name_systematic
;
Pyrazino[2,3-b]indolizine-10-carbonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.260(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8515(5)
_cell_length_b                   14.147(2)
_cell_length_c                   16.606(3)
_cell_measurement_reflns_used    6832
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.99
_cell_volume                     904.6(2)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.4002
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Oxford Diffraction Ruby CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6832
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         3.13
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2008)'
_exptl_crystal_colour            orange-green
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.149
_refine_ls_extinction_coef       0.017(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0400
_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)+(0.0745P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1112
_reflns_number_gt                1186
_reflns_number_total             1606
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww2144.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221548
_cod_database_fobs_code          2221548
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
N N1 0.1906(3) 0.18749(8) 0.01142(7) 0.0395(3) Uani d . 1 . .
C C2 0.3590(4) 0.15549(12) -0.05644(9) 0.0463(4) Uani d . 1 . .
H H2 0.4296 0.0928 -0.0597 0.056 Uiso calc R 1 . .
C C3 0.4196(4) 0.21534(13) -0.11734(10) 0.0541(5) Uani d . 1 . .
H H3 0.5303 0.1943 -0.1632 0.065 Uiso calc R 1 . .
C C4 0.3135(4) 0.31070(13) -0.11094(11) 0.0554(5) Uani d . 1 . .
H H4 0.3574 0.3523 -0.1529 0.066 Uiso calc R 1 . .
C C5 0.1475(4) 0.34299(12) -0.04437(10) 0.0506(4) Uani d . 1 . .
H H5 0.0804 0.4060 -0.0415 0.061 Uiso calc R 1 . .
C C6 0.0772(4) 0.28097(10) 0.02016(9) 0.0412(4) Uani d . 1 . .
C C7 -0.0876(4) 0.29055(10) 0.09485(9) 0.0431(4) Uani d . 1 . .
C C8 -0.0708(4) 0.20124(11) 0.13408(9) 0.0410(4) Uani d . 1 . .
N N9 -0.1882(3) 0.17236(10) 0.20656(8) 0.0500(4) Uani d . 1 . .
C C10 -0.1199(4) 0.08189(13) 0.22182(10) 0.0538(5) Uani d . 1 . .
H H10 -0.1906 0.0569 0.2706 0.065 Uiso calc R 1 . .
C C11 0.0522(4) 0.02209(12) 0.16866(10) 0.0528(4) Uani d . 1 . .
H H11 0.0890 -0.0403 0.1844 0.063 Uiso calc R 1 . .
N N12 0.1684(3) 0.04892(9) 0.09592(8) 0.0482(4) Uani d . 1 . .
C C13 0.1002(3) 0.13879(10) 0.08115(9) 0.0387(4) Uani d . 1 . .
C C14 -0.2351(4) 0.37523(12) 0.12502(10) 0.0528(5) Uani d . 1 . .
N N15 -0.3567(4) 0.44383(12) 0.14836(11) 0.0782(5) Uani d . 1 . .
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'
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
C2 N1 C13 . . 129.87(13) ?
C2 N1 C6 . . 122.96(13) ?
C13 N1 C6 . . 107.18(11) ?
C3 C2 N1 . . 119.85(15) ?
C3 C2 H2 . . 120.1 ?
N1 C2 H2 . . 120.1 ?
C2 C3 C4 . . 119.29(15) ?
C2 C3 H3 . . 120.4 ?
C4 C3 H3 . . 120.4 ?
C5 C4 C3 . . 121.36(16) ?
C5 C4 H4 . . 119.3 ?
C3 C4 H4 . . 119.3 ?
C4 C5 C6 . . 120.35(16) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
N1 C6 C7 . . 109.19(12) ?
N1 C6 C5 . . 116.18(13) ?
C7 C6 C5 . . 134.63(14) ?
C6 C7 C14 . . 125.53(14) ?
C6 C7 C8 . . 107.47(12) ?
C14 C7 C8 . . 126.98(15) ?
N9 C8 C13 . . 122.01(14) ?
N9 C8 C7 . . 131.34(14) ?
C13 C8 C7 . . 106.65(13) ?
C10 N9 C8 . . 112.96(13) ?
N9 C10 C11 . . 123.77(15) ?
N9 C10 H10 . . 118.1 ?
C11 C10 H10 . . 118.1 ?
N12 C11 C10 . . 124.36(15) ?
N12 C11 H11 . . 117.8 ?
C10 C11 H11 . . 117.8 ?
C13 N12 C11 . . 111.60(13) ?
N12 C13 N1 . . 125.19(13) ?
N12 C13 C8 . . 125.30(14) ?
N1 C13 C8 . . 109.50(13) ?
N15 C14 C7 . . 179.0(2) ?
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
N1 C2 . 1.3883(19) ?
N1 C13 . 1.3980(18) ?
N1 C6 . 1.4014(18) ?
C2 C3 . 1.343(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.414(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.368(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.416(2) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.412(2) ?
C7 C14 . 1.422(2) ?
C7 C8 . 1.422(2) ?
C8 N9 . 1.3580(19) ?
C8 C13 . 1.419(2) ?
N9 C10 . 1.330(2) ?
C10 C11 . 1.400(2) ?
C10 H10 . 0.9300 ?
C11 N12 . 1.352(2) ?
C11 H11 . 0.9300 ?
N12 C13 . 1.3201(19) ?
C14 N15 . 1.149(2) ?
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
C2 H2 N12 3_655 0.93 2.61 3.487(2) 157 y
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
C13 N1 C2 C3 . . . . 179.88(14) ?
C6 N1 C2 C3 . . . . 0.1(2) ?
N1 C2 C3 C4 . . . . 0.6(2) ?
C2 C3 C4 C5 . . . . -0.6(2) ?
C3 C4 C5 C6 . . . . -0.1(2) ?
C2 N1 C6 C7 . . . . 179.16(12) ?
C13 N1 C6 C7 . . . . -0.67(14) ?
C2 N1 C6 C5 . . . . -0.79(19) ?
C13 N1 C6 C5 . . . . 179.38(12) ?
C4 C5 C6 N1 . . . . 0.8(2) ?
C4 C5 C6 C7 . . . . -179.16(15) ?
N1 C6 C7 C14 . . . . 179.76(14) ?
C5 C6 C7 C14 . . . . -0.3(3) ?
N1 C6 C7 C8 . . . . 1.01(15) ?
C5 C6 C7 C8 . . . . -179.06(15) ?
C6 C7 C8 N9 . . . . 179.88(14) ?
C14 C7 C8 N9 . . . . 1.2(3) ?
C6 C7 C8 C13 . . . . -0.94(16) ?
C14 C7 C8 C13 . . . . -179.67(14) ?
C13 C8 N9 C10 . . . . 1.07(19) ?
C7 C8 N9 C10 . . . . -179.86(16) ?
C8 N9 C10 C11 . . . . -0.5(2) ?
N9 C10 C11 N12 . . . . -0.1(3) ?
C10 C11 N12 C13 . . . . 0.2(2) ?
C11 N12 C13 N1 . . . . 179.34(12) ?
C11 N12 C13 C8 . . . . 0.4(2) ?
C2 N1 C13 N12 . . . . 1.2(2) ?
C6 N1 C13 N12 . . . . -178.99(13) ?
C2 N1 C13 C8 . . . . -179.75(12) ?
C6 N1 C13 C8 . . . . 0.07(14) ?
N9 C8 C13 N12 . . . . -1.1(2) ?
C7 C8 C13 N12 . . . . 179.60(14) ?
N9 C8 C13 N1 . . . . 179.82(11) ?
C7 C8 C13 N1 . . . . 0.55(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741941
