#------------------------------------------------------------------------------
#$Date: 2017-07-14 04:07:54 +0300 (Fri, 14 Jul 2017) $
#$Revision: 198701 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/04/7120440.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_7120440
loop_
_publ_author_name
'Huynh, Huu-Tri'
'Jeannin, Olivier'
'Fourmigué, Marc'
_publ_section_title
;
 Organic selenocyanates as strong and directional chalcogen bond donors
 for crystal engineering
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC04833E
_journal_year                    2017
_chemical_formula_moiety         'C10 H8 N2 Se2, C10 H8 N2'
_chemical_formula_sum            'C20 H16 N4 Se2'
_chemical_formula_weight         470.29
_chemical_name_systematic
'1,4-bis(selenocyanatomethyl)benzene, 4,4'-bipyridine'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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 - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_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             2017-02-21T16:35:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2017-06-21 deposited with the CCDC.
2017-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                99.421(3)
_cell_angle_beta                 94.558(2)
_cell_angle_gamma                104.661(2)
_cell_formula_units_Z            1
_cell_length_a                   5.3962(4)
_cell_length_b                   7.7356(6)
_cell_length_c                   11.7477(9)
_cell_measurement_reflns_used    4292
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.79
_cell_measurement_theta_min      2.77
_cell_measurement_wavelength     0.71073
_cell_volume                     464.25(6)
_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)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_UB_11      0.005248
_diffrn_orient_matrix_UB_12      -0.091718
_diffrn_orient_matrix_UB_13      0.050414
_diffrn_orient_matrix_UB_21      0.061161
_diffrn_orient_matrix_UB_22      0.100261
_diffrn_orient_matrix_UB_23      0.06967
_diffrn_orient_matrix_UB_31      -0.183094
_diffrn_orient_matrix_UB_32      -0.007987
_diffrn_orient_matrix_UB_33      0.013095
_diffrn_radiation_monochromator  graphite
_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  0.052
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12290
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.551
_diffrn_reflns_theta_min         2.773
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.993
_exptl_absorpt_correction_T_max  0.787
_exptl_absorpt_correction_T_min  0.259
_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    1.682
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2832
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0412
_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)+(0.0273P)²+0.2465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0841
_reflns_Friedel_coverage         0
_reflns_number_gt                2161
_reflns_number_total             2832
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7cc04833e1.cif
_cod_data_source_block           shelx
_cod_database_code               7120440
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.1896(5) 1.0418(4) 0.9294(2) 0.0325(5) Uani 1 1 d . .
H1 H 0.3183 1.0714 0.8822 0.039 Uiso 1 1 calc R U
C2 C 0.1055(5) 0.8638(3) 0.9465(2) 0.0277(5) Uani 1 1 d . .
C3 C -0.0852(5) 0.8248(4) 1.0185(2) 0.0334(6) Uani 1 1 d . .
H3 H -0.1433 0.7069 1.0318 0.04 Uiso 1 1 calc R U
C4 C 0.2178(5) 0.7205(4) 0.8884(2) 0.0328(5) Uani 1 1 d . .
H4A H 0.212 0.6292 0.9365 0.039 Uiso 1 1 calc R U
H4B H 0.3976 0.7749 0.8816 0.039 Uiso 1 1 calc R U
C5 C -0.2554(6) 0.4717(4) 0.7880(3) 0.0417(7) Uani 1 1 d . .
C6 C 0.4968(6) 0.7462(5) 0.5463(3) 0.0572(9) Uani 1 1 d . .
H6 H 0.3629 0.646 0.51 0.069 Uiso 1 1 calc R U
C7 C 0.6924(6) 0.8106(5) 0.4830(3) 0.0543(9) Uani 1 1 d . .
H7 H 0.69 0.7525 0.4069 0.065 Uiso 1 1 calc R U
C8 C 0.8919(5) 0.9613(4) 0.5326(2) 0.0328(6) Uani 1 1 d . .
C9 C 0.8841(6) 1.0369(4) 0.6472(2) 0.0427(7) Uani 1 1 d . .
H9 H 1.0141 1.1379 0.6857 0.051 Uiso 1 1 calc R U
C10 C 0.6811(6) 0.9603(4) 0.7032(3) 0.0467(7) Uani 1 1 d . .
H10 H 0.6804 1.0129 0.7802 0.056 Uiso 1 1 calc R U
N1 N -0.4344(6) 0.3936(4) 0.8211(3) 0.0635(8) Uani 1 1 d . .
N2 N 0.4874(4) 0.8178(4) 0.6555(2) 0.0445(6) Uani 1 1 d . .
Se1 Se 0.03277(5) 0.60064(4) 0.73157(2) 0.03822(11) Uani 1 1 d . .
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
C3 C1 C2 121.0(2) 2_577 .
C3 C1 H1 119.5 2_577 .
C2 C1 H1 119.5 . .
C1 C2 C3 118.0(2) . .
C1 C2 C4 120.4(2) . .
C3 C2 C4 121.6(2) . .
C1 C3 C2 121.0(2) 2_577 .
C1 C3 H3 119.5 2_577 .
C2 C3 H3 119.5 . .
C2 C4 Se1 112.67(17) . .
C2 C4 H4A 109.1 . .
Se1 C4 H4A 109.1 . .
C2 C4 H4B 109.1 . .
Se1 C4 H4B 109.1 . .
H4A C4 H4B 107.8 . .
N1 C5 Se1 178.8(3) . .
N2 C6 C7 124.1(3) . .
N2 C6 H6 117.9 . .
C7 C6 H6 117.9 . .
C6 C7 C8 119.9(3) . .
C6 C7 H7 120.1 . .
C8 C7 H7 120.1 . .
C7 C8 C9 116.3(2) . .
C7 C8 C8 122.2(3) . 2_776
C9 C8 C8 121.4(3) . 2_776
C10 C9 C8 119.1(3) . .
C10 C9 H9 120.4 . .
C8 C9 H9 120.4 . .
N2 C10 C9 124.8(3) . .
N2 C10 H10 117.6 . .
C9 C10 H10 117.6 . .
C10 N2 C6 115.7(3) . .
C5 Se1 C4 94.13(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C3 1.378(4) 2_577
C1 C2 1.390(3) .
C1 H1 0.93 .
C2 C3 1.390(3) .
C2 C4 1.490(4) .
C3 C1 1.378(4) 2_577
C3 H3 0.93 .
C4 Se1 1.982(2) .
C4 H4A 0.97 .
C4 H4B 0.97 .
C5 N1 1.136(4) .
C5 Se1 1.856(3) .
C6 N2 1.321(4) .
C6 C7 1.377(4) .
C6 H6 0.93 .
C7 C8 1.378(4) .
C7 H7 0.93 .
C8 C9 1.385(4) .
C8 C8 1.498(5) 2_776
C9 C10 1.377(4) .
C9 H9 0.93 .
C10 N2 1.321(4) .
C10 H10 0.93 .
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_4
C3 C1 C2 C3 -0.6(4) 2_577 .
C3 C1 C2 C4 179.2(2) 2_577 .
C1 C2 C3 C1 0.6(4) . 2_577
C4 C2 C3 C1 -179.2(2) . 2_577
C1 C2 C4 Se1 -88.3(3) . .
C3 C2 C4 Se1 91.5(3) . .
N2 C6 C7 C8 -1.4(6) . .
C6 C7 C8 C9 1.6(5) . .
C6 C7 C8 C8 -179.3(3) . 2_776
C7 C8 C9 C10 -0.7(4) . .
C8 C8 C9 C10 -179.9(3) 2_776 .
C8 C9 C10 N2 -0.4(5) . .
C9 C10 N2 C6 0.6(5) . .
C7 C6 N2 C10 0.3(5) . .
