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#$Date: 2021-01-09 08:05:55 +0200 (Sat, 09 Jan 2021) $
#$Revision: 260884 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/37/2243717.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_2243717
loop_
_publ_author_name
'Kalle, Paulina'
'Tatarin, Sergei V.'
'Zakharov, Alexander Yu.'
'Kiseleva, Marina A.'
'Bezzubov, Stanislav I.'
_publ_section_title
;
 Synthesis and comparative structural study of
 2-(pyridin-2-yl)-1H-perimidine and its mono- and
 di-N-methylated analogues
;
_journal_coeditor_code           WM5594
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              96
_journal_page_last               100
_journal_paper_doi               10.1107/S205698902100013X
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C16 H11 N3'
_chemical_formula_moiety         'C16 H11 N3'
_chemical_formula_sum            'C16 H11 N3'
_chemical_formula_weight         245.28
_chemical_name_systematic
;
2-(Pyridin-2-yl)-1H-perimidine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.382(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5479(5)
_cell_length_b                   5.0242(2)
_cell_length_c                   17.3881(7)
_cell_measurement_reflns_used    7163
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.270
_cell_measurement_theta_min      3.064
_cell_volume                     1160.29(8)
_computing_cell_refinement
;
SAINT (Bruker, 2017)
;
_computing_data_collection
;
APEX3 (Bruker, 2017)
;
_computing_data_reduction
;
SAINT (Bruker, 2017)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTON III CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16322
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.290
_diffrn_reflns_theta_min         3.497
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.327
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0568
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0570P)²+1.1159P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1402
_reflns_number_gt                2405
_reflns_number_total             2866
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5594sup1.cif
_cod_data_source_block           1
_cod_original_cell_volume        1160.28(8)
_cod_database_code               2243717
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.67572(10) 0.4402(3) 0.27627(8) 0.0154(3) Uani d 1 . .
N N3 0.71391(10) 0.0786(3) 0.17704(8) 0.0168(3) Uani d 1 . .
N N2 0.84493(10) 0.5837(3) 0.30290(8) 0.0155(3) Uani d 1 . .
C C12 0.79419(12) 0.2223(3) 0.21158(9) 0.0143(3) Uani d 1 . .
C C10 0.64357(12) 0.6204(3) 0.32655(9) 0.0149(3) Uani d 1 . .
C C1 0.77359(12) 0.4307(3) 0.26757(9) 0.0142(3) Uani d 1 . .
C C2 0.81956(12) 0.7734(3) 0.35506(9) 0.0150(3) Uani d 1 . .
C C13 0.89068(12) 0.1825(3) 0.19733(9) 0.0156(3) Uani d 1 . .
C C3 0.89194(13) 0.9430(3) 0.39534(9) 0.0174(3) Uani d 1 . .
C C8 0.52046(13) 0.8239(4) 0.38981(10) 0.0200(4) Uani d 1 . .
C C16 0.72925(13) -0.1115(3) 0.12658(10) 0.0189(4) Uani d 1 . .
C C15 0.82269(13) -0.1659(3) 0.10900(9) 0.0191(4) Uani d 1 . .
C C9 0.54570(12) 0.6318(3) 0.33781(9) 0.0182(3) Uani d 1 . .
C C6 0.69204(12) 0.9893(3) 0.41877(9) 0.0168(3) Uani d 1 . .
C C5 0.76845(13) 1.1625(3) 0.45756(9) 0.0186(3) Uani d 1 . .
C C14 0.90460(13) -0.0168(3) 0.14534(10) 0.0181(3) Uani d 1 . .
C C11 0.71827(12) 0.7951(3) 0.36697(9) 0.0145(3) Uani d 1 . .
C C7 0.59039(13) 0.9992(4) 0.42875(10) 0.0201(4) Uani d 1 . .
C C4 0.86549(13) 1.1376(3) 0.44599(9) 0.0187(4) Uani d 1 . .
H H3 0.9603(15) 0.931(4) 0.3862(11) 0.020(5) Uiso d 1 . .
H H13 0.9452(16) 0.282(4) 0.2226(12) 0.024(5) Uiso d 1 . .
H H8 0.4528(16) 0.829(4) 0.3965(12) 0.024(5) Uiso d 1 . .
H H14 0.9698(17) -0.050(5) 0.1362(13) 0.031(6) Uiso d 1 . .
H H9 0.4957(14) 0.510(4) 0.3102(11) 0.016(5) Uiso d 1 . .
H H7 0.5720(16) 1.125(5) 0.4625(13) 0.030(6) Uiso d 1 . .
H H4 0.9168(15) 1.252(4) 0.4733(12) 0.023(5) Uiso d 1 . .
H H16 0.6709(15) -0.203(4) 0.1022(12) 0.024(5) Uiso d 1 . .
H H1 0.6349(17) 0.326(5) 0.2490(13) 0.032(6) Uiso d 1 . .
H H5 0.7526(14) 1.292(4) 0.4910(12) 0.019(5) Uiso d 1 . .
H H15 0.8299(15) -0.302(4) 0.0730(12) 0.024(5) Uiso 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
C10 N1 H1 . . 122.0(15) ?
C1 N1 C10 . . 121.71(14) ?
C1 N1 H1 . . 116.3(15) ?
C16 N3 C12 . . 117.31(14) ?
C1 N2 C2 . . 117.11(14) ?
N3 C12 C1 . . 115.40(14) ?
N3 C12 C13 . . 123.28(15) ?
C13 C12 C1 . . 121.31(14) ?
N1 C10 C11 . . 115.76(14) ?
C9 C10 N1 . . 123.16(15) ?
C9 C10 C11 . . 121.09(15) ?
N1 C1 C12 . . 114.06(14) ?
N2 C1 N1 . . 125.35(15) ?
N2 C1 C12 . . 120.59(14) ?
N2 C2 C11 . . 120.58(14) ?
C3 C2 N2 . . 120.44(14) ?
C3 C2 C11 . . 118.98(15) ?
C12 C13 H13 . . 121.8(13) ?
C14 C13 C12 . . 118.23(15) ?
C14 C13 H13 . . 119.9(13) ?
C2 C3 C4 . . 120.17(15) ?
C2 C3 H3 . . 118.9(12) ?
C4 C3 H3 . . 120.9(12) ?
C9 C8 H8 . . 117.3(13) ?
C7 C8 C9 . . 121.68(15) ?
C7 C8 H8 . . 121.0(13) ?
N3 C16 C15 . . 123.42(15) ?
N3 C16 H16 . . 114.7(13) ?
C15 C16 H16 . . 121.8(13) ?
C16 C15 H15 . . 120.4(12) ?
C14 C15 C16 . . 118.52(15) ?
C14 C15 H15 . . 121.0(12) ?
C10 C9 C8 . . 118.76(15) ?
C10 C9 H9 . . 120.1(11) ?
C8 C9 H9 . . 121.1(11) ?
C5 C6 C11 . . 118.24(15) ?
C5 C6 C7 . . 123.66(15) ?
C11 C6 C7 . . 118.11(15) ?
C6 C5 H5 . . 119.6(12) ?
C4 C5 C6 . . 120.29(15) ?
C4 C5 H5 . . 120.2(12) ?
C13 C14 H14 . . 119.4(14) ?
C15 C14 C13 . . 119.24(15) ?
C15 C14 H14 . . 121.4(14) ?
C10 C11 C2 . . 119.48(14) ?
C10 C11 C6 . . 119.78(14) ?
C6 C11 C2 . . 120.74(15) ?
C8 C7 C6 . . 120.58(15) ?
C8 C7 H7 . . 120.3(13) ?
C6 C7 H7 . . 119.2(13) ?
C3 C4 H4 . . 118.7(12) ?
C5 C4 C3 . . 121.57(15) ?
C5 C4 H4 . . 119.8(12) ?
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 C10 . 1.387(2) ?
N1 C1 . 1.365(2) ?
N1 H1 . 0.87(2) ?
N3 C12 . 1.344(2) ?
N3 C16 . 1.341(2) ?
N2 C1 . 1.292(2) ?
N2 C2 . 1.404(2) ?
C12 C1 . 1.493(2) ?
C12 C13 . 1.392(2) ?
C10 C9 . 1.379(2) ?
C10 C11 . 1.417(2) ?
C2 C3 . 1.381(2) ?
C2 C11 . 1.432(2) ?
C13 C14 . 1.387(2) ?
C13 H13 . 0.93(2) ?
C3 C4 . 1.409(2) ?
C3 H3 . 0.97(2) ?
C8 C9 . 1.410(2) ?
C8 C7 . 1.371(2) ?
C8 H8 . 0.95(2) ?
C16 C15 . 1.387(2) ?
C16 H16 . 0.94(2) ?
C15 C14 . 1.384(2) ?
C15 H15 . 0.94(2) ?
C9 H9 . 0.97(2) ?
C6 C5 . 1.417(2) ?
C6 C11 . 1.420(2) ?
C6 C7 . 1.422(2) ?
C5 C4 . 1.374(2) ?
C5 H5 . 0.93(2) ?
C14 H14 . 0.94(2) ?
C7 H7 . 0.93(2) ?
C4 H4 . 0.95(2) ?
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
N1 C10 C9 C8 . . . . -179.50(15) ?
N1 C10 C11 C2 . . . . -1.0(2) ?
N1 C10 C11 C6 . . . . 179.00(14) ?
N3 C12 C1 N1 . . . . 1.1(2) ?
N3 C12 C1 N2 . . . . -178.67(14) ?
N3 C12 C13 C14 . . . . -0.5(2) ?
N3 C16 C15 C14 . . . . 0.1(3) ?
N2 C2 C3 C4 . . . . 178.31(14) ?
N2 C2 C11 C10 . . . . 1.0(2) ?
N2 C2 C11 C6 . . . . -179.07(14) ?
C12 N3 C16 C15 . . . . 0.2(2) ?
C12 C13 C14 C15 . . . . 0.8(2) ?
C10 N1 C1 N2 . . . . -0.8(2) ?
C10 N1 C1 C12 . . . . 179.41(13) ?
C1 N1 C10 C9 . . . . -178.72(15) ?
C1 N1 C10 C11 . . . . 1.0(2) ?
C1 N2 C2 C3 . . . . 179.62(14) ?
C1 N2 C2 C11 . . . . -0.7(2) ?
C1 C12 C13 C14 . . . . 179.19(14) ?
C2 N2 C1 N1 . . . . 0.7(2) ?
C2 N2 C1 C12 . . . . -179.58(13) ?
C2 C3 C4 C5 . . . . 0.8(2) ?
C13 C12 C1 N1 . . . . -178.61(14) ?
C13 C12 C1 N2 . . . . 1.6(2) ?
C3 C2 C11 C10 . . . . -179.38(14) ?
C3 C2 C11 C6 . . . . 0.6(2) ?
C16 N3 C12 C1 . . . . -179.71(13) ?
C16 N3 C12 C13 . . . . 0.0(2) ?
C16 C15 C14 C13 . . . . -0.6(2) ?
C9 C10 C11 C2 . . . . 178.63(15) ?
C9 C10 C11 C6 . . . . -1.3(2) ?
C9 C8 C7 C6 . . . . -1.1(3) ?
C6 C5 C4 C3 . . . . 0.5(2) ?
C5 C6 C11 C10 . . . . -179.34(14) ?
C5 C6 C11 C2 . . . . 0.7(2) ?
C5 C6 C7 C8 . . . . -179.48(16) ?
C11 C10 C9 C8 . . . . 0.8(2) ?
C11 C2 C3 C4 . . . . -1.3(2) ?
C11 C6 C5 C4 . . . . -1.3(2) ?
C11 C6 C7 C8 . . . . 0.6(2) ?
C7 C8 C9 C10 . . . . 0.4(3) ?
C7 C6 C5 C4 . . . . 178.83(16) ?
C7 C6 C11 C10 . . . . 0.6(2) ?
C7 C6 C11 C2 . . . . -179.37(14) ?

_cod_database_fobs_code 2243717
