#------------------------------------------------------------------------------
#$Date: 2023-10-06 03:03:32 +0300 (Fri, 06 Oct 2023) $
#$Revision: 286729 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/72/7247282.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_7247282
loop_
_publ_author_name
'Alfuth, Jan'
'Jeannin, Olivier'
'Fourmigué, Marc'
_publ_section_title
;
 Chalcogen bonding interactions in a series of aromatic selenocyanates
;
_journal_issue                   37
_journal_name_full               CrystEngComm
_journal_page_first              5316
_journal_page_last               5323
_journal_paper_doi               10.1039/D3CE00745F
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C8 H4 N2 Se2'
_chemical_formula_sum            'C8 H4 N2 Se2'
_chemical_formula_weight         286.05
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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     dual
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2023-01-17T17:17:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2023-08-29 deposited with the CCDC.	2023-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.910(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.1170(12)
_cell_length_b                   4.0552(5)
_cell_length_c                   11.8113(13)
_cell_measurement_reflns_used    3122
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.25
_cell_measurement_wavelength     0.71073
_cell_volume                     434.36(9)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      0.07731
_diffrn_orient_matrix_UB_12      0.167751
_diffrn_orient_matrix_UB_13      0.02425
_diffrn_orient_matrix_UB_21      0.075039
_diffrn_orient_matrix_UB_22      -0.13529
_diffrn_orient_matrix_UB_23      -0.035161
_diffrn_orient_matrix_UB_31      -0.0235
_diffrn_orient_matrix_UB_32      0.119864
_diffrn_orient_matrix_UB_33      -0.073625
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4064
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.472
_diffrn_reflns_theta_min         3.934
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.451
_exptl_absorpt_correction_T_max  0.776
_exptl_absorpt_correction_T_min  0.608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     55
_refine_ls_number_reflns         958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0184
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0119P)²+0.3115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0422
_refine_ls_wR_factor_ref         0.0435
_reflns_Friedel_coverage         0
_reflns_number_gt                850
_reflns_number_total             958
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00745f2.cif
_cod_data_source_block           shelx_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7247280--7247285.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7247282
_shelx_res_file
;
 
    shelx.res created by SHELXL-2014/7
 
 
TITL shelxt_a.res in P2(1)/c
CELL  0.71073   9.1170   4.0552  11.8113   90.000   95.910   90.000
ZERR     2.00   0.0012   0.0005   0.0013    0.000    0.005    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    SE
UNIT  16 8 4 4
MERG   2
FMAP   2
PLAN   20
BOND   $H
CONF
ACTA
LIST   4
L.S.  10
TEMP  -123.00
WGHT    0.011900    0.311500
FVAR       0.78716
C1    1    0.468636    0.322912    0.399203    11.00000    0.01690    0.01990 =
         0.01607   -0.00291    0.00158   -0.00025
AFIX  43
H1    2    0.446708    0.202349    0.330584    11.00000   -1.20000
AFIX   0
C2    1    0.357385    0.397445    0.467585    11.00000    0.01158    0.01534 =
         0.01633    0.00227   -0.00146    0.00019
C3    1    0.387830    0.573361    0.567697    11.00000    0.01455    0.01969 =
         0.01739    0.00022    0.00337    0.00123
AFIX  43
H3    2    0.311071    0.623063    0.613604    11.00000   -1.20000
AFIX   0
C4    1    0.152134    0.351939    0.277091    11.00000    0.01168    0.02067 =
         0.01958   -0.00057    0.00000    0.00046
N1    3    0.145937    0.413999    0.181671    11.00000    0.01857    0.03611 =
         0.02030    0.00293    0.00055   -0.00169
SE1   4    0.157703    0.244084    0.429412    11.00000    0.01257    0.02185 =
         0.01480    0.00190   -0.00014   -0.00295
HKLF    4
 
REM  shelxt_a.res in P2(1)/c
REM R1 =  0.0184 for     850 Fo > 4sig(Fo)  and  0.0214 for all     958 data
REM     55 parameters refined using      0 restraints
 
END
 
WGHT      0.0126      0.3006
 
REM Highest difference peak  0.305,  deepest hole -0.514,  1-sigma level  0.084
Q1    1   0.3639  0.5539  0.5030  11.00000  0.05    0.30
Q2    1   0.3943  0.4350  0.4204  11.00000  0.05    0.28
Q3    1   0.6017  0.0985  0.2604  11.00000  0.05    0.25
Q4    1   0.1072  0.2559  0.5471  11.00000  0.05    0.25
Q5    1   0.4203  0.2959  0.4529  11.00000  0.05    0.23
Q6    1   0.4673  0.5380  0.5917  11.00000  0.05    0.22
Q7    1   0.3792  0.7117  0.5611  11.00000  0.05    0.22
Q8    1   0.1400  0.2613  0.1389  11.00000  0.05    0.21
Q9    1   0.1461  0.3097  0.3326  11.00000  0.05    0.20
Q10   1   0.5040  0.1776  0.5196  11.00000  0.05    0.20
Q11   1   0.5356 -0.1977  0.3599  11.00000  0.05    0.19
Q12   1   0.0044  0.2615  0.0554  11.00000  0.05    0.18
Q13   1  -0.0405  0.3952  0.4779  11.00000  0.05    0.18
Q14   1   0.0159  0.5368  0.3995  11.00000  0.05    0.18
Q15   1   0.3067  0.3587  0.4544  11.00000  0.05    0.18
Q16   1   0.0466  0.4988  0.5397  11.00000  0.05    0.18
Q17   1   0.4115  0.2967  0.6156  11.00000  0.05    0.18
Q18   1   0.0453  0.4497  0.0516  11.00000  0.05    0.18
Q19   1   0.3773  0.8752  0.4777  11.00000  0.05    0.17
Q20   1   0.4085  0.7406  0.4177  11.00000  0.05    0.17
;
_shelx_res_checksum              98838
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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4686(2) 0.3229(5) 0.39920(16) 0.0176(4) Uani 1 1 d . . . . .
H1 H 0.4467 0.2023 0.3306 0.021 Uiso 1 1 calc R U . . .
C2 C 0.35738(18) 0.3974(4) 0.46758(15) 0.0146(3) Uani 1 1 d . . . . .
C3 C 0.3878(2) 0.5734(5) 0.56770(15) 0.0171(4) Uani 1 1 d . . . . .
H3 H 0.3111 0.6231 0.6136 0.021 Uiso 1 1 calc R U . . .
C4 C 0.15213(19) 0.3519(5) 0.27709(16) 0.0174(3) Uani 1 1 d . . . . .
N1 N 0.14594(17) 0.4140(5) 0.18167(13) 0.0251(4) Uani 1 1 d . . . . .
Se1 Se 0.15770(2) 0.24408(4) 0.42941(2) 0.01652(9) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0169(9) 0.0199(9) 0.0161(9) -0.0029(7) 0.0016(7) -0.0003(7)
C2 0.0116(8) 0.0153(8) 0.0163(8) 0.0023(7) -0.0015(6) 0.0002(6)
C3 0.0146(8) 0.0197(9) 0.0174(9) 0.0002(7) 0.0034(6) 0.0012(7)
C4 0.0117(8) 0.0207(8) 0.0196(9) -0.0006(7) 0.0000(6) 0.0005(7)
N1 0.0186(8) 0.0361(11) 0.0203(9) 0.0029(7) 0.0006(7) -0.0017(7)
Se1 0.01257(11) 0.02185(13) 0.01480(12) 0.00190(6) -0.00014(7) -0.00295(6)
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 0 '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'
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
C3 C1 C2 119.42(17) 3_666 . ?
C3 C1 H1 120.3 3_666 . ?
C2 C1 H1 120.3 . . ?
C3 C2 C1 120.87(16) . . ?
C3 C2 Se1 117.79(12) . . ?
C1 C2 Se1 121.29(13) . . ?
C2 C3 C1 119.72(16) . 3_666 ?
C2 C3 H3 120.1 . . ?
C1 C3 H3 120.1 3_666 . ?
N1 C4 Se1 178.38(18) . . ?
C4 Se1 C2 94.69(8) . . ?
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
C1 C3 1.392(3) 3_666 ?
C1 C2 1.393(2) . ?
C1 H1 0.95 . ?
C2 C3 1.384(2) . ?
C2 Se1 1.9327(17) . ?
C3 C1 1.392(3) 3_666 ?
C3 H3 0.95 . ?
C4 N1 1.150(2) . ?
C4 Se1 1.8471(19) . ?
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
C3 C1 C2 C3 0.1(3) 3_666 . . . ?
C3 C1 C2 Se1 -177.34(13) 3_666 . . . ?
C1 C2 C3 C1 -0.1(3) . . . 3_666 ?
Se1 C2 C3 C1 177.43(14) . . . 3_666 ?
