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#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/11/7051146.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_7051146
loop_
_publ_author_name
'Boryczka, Stanisław'
'Rozenberg, Mark S.'
'Schreurs, Antoine M. M.'
'Kroon, Jan'
'Starikov, Evgeni B.'
'Steiner, Thomas'
_publ_section_title
;
 A short C--H···N hydrogen bond with a very strong
 IR spectroscopic effect
;
_journal_issue                   9
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1111
_journal_paper_doi               10.1039/b102727c
_journal_volume                  25
_journal_year                    2001
_chemical_formula_sum            'C13 H11 N S Se'
_chemical_formula_weight         292.25
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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                75.170(2)
_cell_angle_beta                 71.033(3)
_cell_angle_gamma                63.780(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6112(3)
_cell_length_b                   8.8243(3)
_cell_length_c                   9.2589(3)
_cell_measurement_temperature    125(2)
_cell_volume                     591.64(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8849
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    3.319
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.413
_refine_diff_density_min         -1.221
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0744P)²+0.2890P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1089
_reflns_number_gt                2425
_reflns_number_total             2704
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b102727c.txt
_cod_data_source_block           (I)
_cod_original_cell_volume        591.65(3)
_cod_database_code               7051146
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
Se1 Se 0.12795(4) 0.82797(3) 0.13401(3) 0.01666(13) Uani 1 1 d . . .
S1 S 0.14014(10) 0.46468(9) 0.11853(9) 0.01803(18) Uani 1 1 d . . .
N1 N 0.2640(3) 0.3612(3) 0.5272(3) 0.0182(5) Uani 1 1 d . . .
C2 C 0.2270(4) 0.3505(4) 0.4048(4) 0.0184(6) Uani 1 1 d . . .
H2 H 0.2276 0.2449 0.3969 0.037(12) Uiso 1 1 calc R . .
C3 C 0.1859(4) 0.4858(4) 0.2825(3) 0.0146(6) Uani 1 1 d . . .
C4 C 0.1847(4) 0.6400(3) 0.2944(3) 0.0136(5) Uani 1 1 d . . .
C5 C 0.2235(4) 0.6569(4) 0.4270(3) 0.0151(6) Uani 1 1 d . . .
C6 C 0.2253(4) 0.8096(4) 0.4503(4) 0.0193(6) Uani 1 1 d . . .
H6 H 0.1961 0.9085 0.3767 0.032(11) Uiso 1 1 calc R . .
C7 C 0.2688(4) 0.8144(4) 0.5784(4) 0.0243(7) Uani 1 1 d . . .
H7 H 0.2717 0.9163 0.5916 0.030(11) Uiso 1 1 calc R . .
C8 C 0.3094(4) 0.6702(4) 0.6912(4) 0.0239(7) Uani 1 1 d . . .
H8 H 0.3385 0.6757 0.7797 0.045(13) Uiso 1 1 calc R . .
C9 C 0.3068(4) 0.5220(4) 0.6724(4) 0.0199(6) Uani 1 1 d . . .
H9 H 0.3336 0.4254 0.7487 0.009(8) Uiso 1 1 calc R . .
C10 C 0.2645(4) 0.5120(4) 0.5404(3) 0.0164(6) Uani 1 1 d . . .
C11 C 0.1463(4) 0.2504(4) 0.1590(4) 0.0222(7) Uani 1 1 d . . .
H11A H 0.2673 0.1682 0.1642 0.029(10) Uiso 1 1 calc R . .
H11B H 0.1126 0.2293 0.0769 0.033(11) Uiso 1 1 calc R . .
H11C H 0.0624 0.2377 0.2578 0.043(13) Uiso 1 1 calc R . .
C12 C 0.3768(4) 0.8092(4) 0.0388(4) 0.0201(6) Uani 1 1 d . . .
H12A H 0.4241 0.8308 0.1123 0.040(12) Uiso 1 1 calc R . .
H12B H 0.4540 0.6934 0.0102 0.034(11) Uiso 1 1 calc R . .
C13 C 0.3743(4) 0.9364(4) -0.0986(4) 0.0182(6) Uani 1 1 d . . .
C14 C 0.3654(4) 1.0419(4) -0.2078(4) 0.0215(6) Uani 1 1 d . . .
H14 H 0.3583 1.1265 -0.2955 0.037(12) Uiso 1 1 calc R . .
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'
Se Se -0.0929 2.2259 '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
C4 Se1 C12 95.85(12) . . ?
C3 S1 C11 103.24(15) . . ?
C2 N1 C10 118.6(3) . . ?
N1 C2 C3 124.6(3) . . ?
N1 C2 H2 117.7 . . ?
C3 C2 H2 117.7 . . ?
C4 C3 C2 117.6(3) . . ?
C4 C3 S1 119.3(2) . . ?
C2 C3 S1 123.1(2) . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 Se1 119.5(2) . . ?
C5 C4 Se1 121.1(2) . . ?
C10 C5 C6 118.6(3) . . ?
C10 C5 C4 117.7(3) . . ?
C6 C5 C4 123.7(3) . . ?
C7 C6 C5 120.3(3) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 121.0(3) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
N1 C10 C9 118.3(3) . . ?
N1 C10 C5 122.1(3) . . ?
C9 C10 C5 119.6(3) . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 Se1 107.5(2) . . ?
C13 C12 H12A 110.2 . . ?
Se1 C12 H12A 110.2 . . ?
C13 C12 H12B 110.2 . . ?
Se1 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C14 C13 C12 177.5(3) . . ?
C13 C14 H14 180.0 . . ?
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
Se1 C4 1.921(3) . ?
Se1 C12 1.982(3) . ?
S1 C3 1.758(3) . ?
S1 C11 1.811(3) . ?
N1 C2 1.308(4) . ?
N1 C10 1.369(4) . ?
C2 C3 1.424(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(4) . ?
C4 C5 1.430(4) . ?
C5 C10 1.420(4) . ?
C5 C6 1.426(4) . ?
C6 C7 1.370(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.413(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.373(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.417(4) . ?
C9 H9 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.465(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.183(4) . ?
C14 H14 0.9500 . ?
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
C14 H14 N1 0.95 2.30 3.225(4) 164.9 1_564
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
C10 N1 C2 C3 -0.3(4) . . . . ?
N1 C2 C3 C4 -0.1(4) . . . . ?
N1 C2 C3 S1 179.0(2) . . . . ?
C11 S1 C3 C4 -177.4(2) . . . . ?
C11 S1 C3 C2 3.5(3) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
S1 C3 C4 C5 -179.4(2) . . . . ?
C2 C3 C4 Se1 -179.4(2) . . . . ?
S1 C3 C4 Se1 1.4(3) . . . . ?
C12 Se1 C4 C3 -103.9(2) . . . . ?
C12 Se1 C4 C5 76.9(2) . . . . ?
C3 C4 C5 C10 0.9(4) . . . . ?
Se1 C4 C5 C10 -179.9(2) . . . . ?
C3 C4 C5 C6 -179.8(3) . . . . ?
Se1 C4 C5 C6 -0.7(4) . . . . ?
C10 C5 C6 C7 1.1(4) . . . . ?
C4 C5 C6 C7 -178.1(3) . . . . ?
C5 C6 C7 C8 -1.2(5) . . . . ?
C6 C7 C8 C9 0.5(5) . . . . ?
C7 C8 C9 C10 0.3(5) . . . . ?
C2 N1 C10 C9 -179.2(3) . . . . ?
C2 N1 C10 C5 1.0(4) . . . . ?
C8 C9 C10 N1 179.9(3) . . . . ?
C8 C9 C10 C5 -0.3(4) . . . . ?
C6 C5 C10 N1 179.4(3) . . . . ?
C4 C5 C10 N1 -1.4(4) . . . . ?
C6 C5 C10 C9 -0.4(4) . . . . ?
C4 C5 C10 C9 178.9(3) . . . . ?
C4 Se1 C12 C13 176.3(2) . . . . ?
Se1 C12 C13 C14 12(8) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4416248
