#------------------------------------------------------------------------------
#$Date: 2023-10-06 03:03:32 +0300 (Fri, 06 Oct 2023) $
#$Revision: 286729 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/72/7247281.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_7247281
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           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      62
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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             2021-11-29T16:07:28-00:00
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.563(6)
_cell_length_b                   17.139(8)
_cell_length_c                   4.8436(19)
_cell_measurement_reflns_used    894
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.6
_cell_measurement_theta_min      3.52
_cell_measurement_wavelength     0.71073
_cell_volume                     959.9(8)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (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      293(2)
_diffrn_detector                 CCD-LDI-APEX2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_orient_matrix_UB_11      -0.063412
_diffrn_orient_matrix_UB_12      -0.039673
_diffrn_orient_matrix_UB_13      0.00171
_diffrn_orient_matrix_UB_21      -0.058812
_diffrn_orient_matrix_UB_22      0.042775
_diffrn_orient_matrix_UB_23      -0.002105
_diffrn_orient_matrix_UB_31      0.000075
_diffrn_orient_matrix_UB_32      -0.000765
_diffrn_orient_matrix_UB_33      -0.20644
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0792
_diffrn_reflns_av_unetI/netI     0.0805
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            5309
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.524
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.648
_exptl_absorpt_correction_T_max  0.858
_exptl_absorpt_correction_T_min  0.582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.979
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.056
_refine_diff_density_min         -1.424
_refine_diff_density_rms         0.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     58
_refine_ls_number_reflns         1132
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1206
_refine_ls_R_factor_gt           0.0688
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1224P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1798
_refine_ls_wR_factor_ref         0.2156
_reflns_Friedel_coverage         0
_reflns_number_gt                672
_reflns_number_total             1132
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00745f2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7247280--7247285.cif.'
_cod_database_code               7247281
_shelx_res_file
;
 
    shelx.res created by SHELXL-2014/7
 
TITL shelxt_a.res in Pnma
CELL  0.71073  11.5630  17.1390   4.8436   90.000   90.000   90.000
ZERR     4.00   0.0060   0.0080   0.0019    0.000    0.000    0.000
LATT   1
SYMM  1/2 - X, - Y, 1/2 + Z
SYMM  - X, 1/2 + Y, - Z
SYMM  1/2 + X, 1/2 - Y, 1/2 - Z
SFAC  C    H    N    SE
UNIT  32 16 8 8
MERG   2
FMAP   2
PLAN   20
BOND   $H
conf
acta
LIST   4
L.S.  10
WGHT    0.122400
FVAR       0.41180
C1    1    0.470604    0.680441    0.855336    11.00000    0.04173    0.03444 =
         0.05617   -0.00342    0.01393   -0.00120
C2    1    0.427998    0.750000    0.744373    10.50000    0.03525    0.03957 =
         0.05896    0.00000    0.00326    0.00000
AFIX  43
H2    2    0.373652    0.750000    0.602831    10.50000   -1.20000
AFIX   0
C3    1    0.595576    0.750000    1.155486    10.50000    0.05725    0.08229 =
         0.06281    0.00000   -0.01637    0.00000
AFIX  43
H3    2    0.653136    0.750000    1.289590    10.50000   -1.20000
AFIX   0
C4    1    0.554265    0.680639    1.059242    11.00000    0.04929    0.05807 =
         0.05797    0.01067   -0.00374    0.00670
AFIX  43
H4    2    0.582130    0.633849    1.130163    11.00000   -1.20000
AFIX   0
C5    1    0.276757    0.580103    0.854469    11.00000    0.04411    0.03500 =
         0.07344    0.00109   -0.00261    0.00197
N1    3    0.186537    0.576901    0.947451    11.00000    0.04719    0.06757 =
         0.09486   -0.00235    0.02083   -0.01133
SE1   4    0.422844    0.581076    0.696368    11.00000    0.04843    0.04078 =
         0.09337   -0.00991    0.02079   -0.00533
HKLF    4
 
REM  shelxt_a.res in Pnma
REM R1 =  0.0688 for     672 Fo > 4sig(Fo)  and  0.1206 for all    1132 data
REM     58 parameters refined using      0 restraints
 
END
 
WGHT      0.1224      0.0000
 
REM Highest difference peak  1.056,  deepest hole -1.424,  1-sigma level  0.240
Q1    1   0.3774  0.6081  0.5420  11.00000  0.05    1.06
Q2    1   0.0802  0.5085  1.0046  11.00000  0.05    0.51
Q3    1   0.3192  0.5019  0.9815  11.00000  0.05    0.49
Q4    1   0.5435  0.6539  1.0197  11.00000  0.05    0.48
Q5    1   0.0792  0.5724  1.1001  11.00000  0.05    0.47
Q6    1   0.5977  0.7500  1.0329  10.50000  0.05    0.47
Q7    1   0.5932  0.5815  1.0050  11.00000  0.05    0.47
Q8    1   0.2181  0.5812  1.0793  11.00000  0.05    0.46
Q9    1   0.4751  0.5463  0.4510  11.00000  0.05    0.46
Q10   1   0.5810  0.5668  1.0368  11.00000  0.05    0.45
Q11   1   0.4359  0.7201  0.8705  11.00000  0.05    0.45
Q12   1   0.2436  0.4975  1.0141  11.00000  0.05    0.45
Q13   1   0.1221  0.5730  0.9895  11.00000  0.05    0.41
Q14   1   0.6822  0.6761  1.0389  11.00000  0.05    0.41
Q15   1   0.3702  0.5921  1.0467  11.00000  0.05    0.41
Q16   1   0.3402  0.5831  0.4104  11.00000  0.05    0.41
Q17   1   0.5129  0.5829  0.4206  11.00000  0.05    0.40
Q18   1   0.6889  0.5733  1.0011  11.00000  0.05    0.39
Q19   1   0.3216  0.5776  1.0294  11.00000  0.05    0.39
Q20   1   0.3793  0.5500  0.4911  11.00000  0.05    0.39
;
_shelx_res_checksum              95282
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, 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 0.4706(7) 0.6804(4) 0.8553(17) 0.0441(19) Uani 1 1 d . . . . .
C2 C 0.4280(8) 0.75 0.744(2) 0.045(3) Uani 1 2 d S T P . .
H2 H 0.3737 0.75 0.6028 0.054 Uiso 1 2 calc R U P . .
C3 C 0.5956(11) 0.75 1.155(3) 0.067(4) Uani 1 2 d S T P . .
H3 H 0.6531 0.75 1.2896 0.081 Uiso 1 2 calc R U P . .
C4 C 0.5543(7) 0.6806(5) 1.059(2) 0.055(2) Uani 1 1 d . . . . .
H4 H 0.5821 0.6338 1.1302 0.066 Uiso 1 1 calc R U . . .
C5 C 0.2768(7) 0.5801(4) 0.854(2) 0.051(2) Uani 1 1 d . . . . .
N1 N 0.1865(6) 0.5769(4) 0.947(2) 0.070(2) Uani 1 1 d . . . . .
Se1 Se 0.42284(8) 0.58108(5) 0.6964(3) 0.0609(5) 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 0.042(4) 0.034(4) 0.056(5) -0.003(4) 0.014(4) -0.001(3)
C2 0.035(5) 0.040(6) 0.059(8) 0 0.003(5) 0
C3 0.057(8) 0.082(11) 0.063(10) 0 -0.016(6) 0
C4 0.049(5) 0.058(5) 0.058(6) 0.011(5) -0.004(4) 0.007(4)
C5 0.044(5) 0.035(4) 0.073(6) 0.001(4) -0.003(4) 0.002(3)
N1 0.047(4) 0.068(6) 0.095(6) -0.002(4) 0.021(4) -0.011(3)
Se1 0.0484(6) 0.0408(6) 0.0934(10) -0.0099(5) 0.0208(5) -0.0053(3)
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
C4 C1 C2 121.3(8) . . ?
C4 C1 Se1 118.9(7) . . ?
C2 C1 Se1 119.6(7) . . ?
C1 C2 C1 117.1(11) 7_575 . ?
C1 C2 H2 121.4 7_575 . ?
C1 C2 H2 121.4 . . ?
C4 C3 C4 121.4(12) 7_575 . ?
C4 C3 H3 119.3 7_575 . ?
C4 C3 H3 119.3 . . ?
C3 C4 C1 119.4(9) . . ?
C3 C4 H4 120.3 . . ?
C1 C4 H4 120.3 . . ?
N1 C5 Se1 177.5(8) . . ?
C5 Se1 C1 95.9(3) . . ?
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 C4 1.382(12) . ?
C1 C2 1.397(10) . ?
C1 Se1 1.949(8) . ?
C2 C1 1.397(10) 7_575 ?
C2 H2 0.93 . ?
C3 C4 1.363(11) 7_575 ?
C3 C4 1.363(11) . ?
C3 H3 0.93 . ?
C4 H4 0.93 . ?
C5 N1 1.138(11) . ?
C5 Se1 1.855(9) . ?
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
C4 C1 C2 C1 -2.2(15) . . . 7_575 ?
Se1 C1 C2 C1 -176.2(5) . . . 7_575 ?
C4 C3 C4 C1 1(2) 7_575 . . . ?
C2 C1 C4 C3 0.4(15) . . . . ?
Se1 C1 C4 C3 174.4(9) . . . . ?
