#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:04:42 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230369 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/71/7057105.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_7057105
loop_
_publ_author_name
'Jeannin, Olivier'
'Huynh, Huu-Tri'
'Riel, Asia Marie S.'
'Fourmigué, Marc'
_publ_section_title
;
 Chalcogen bonding interactions in organic selenocyanates: from
 cooperativity to chelation
;
_journal_issue                   13
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10502
_journal_paper_doi               10.1039/C8NJ00554K
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C14 H10 N4 Se4'
_chemical_formula_sum            'C14 H10 N4 Se4'
_chemical_formula_weight         550.1
_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
_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             2017-03-08T15:43:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2018-01-31 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.451(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.4173(12)
_cell_length_b                   13.172(3)
_cell_length_c                   11.795(2)
_cell_measurement_reflns_used    1197
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.14
_cell_measurement_theta_min      2.33
_cell_measurement_wavelength     0.71073
_cell_volume                     834.5(3)
_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 0.992
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_UB_11      -0.152531
_diffrn_orient_matrix_UB_12      -0.034956
_diffrn_orient_matrix_UB_13      0.019876
_diffrn_orient_matrix_UB_21      -0.097579
_diffrn_orient_matrix_UB_22      0.027344
_diffrn_orient_matrix_UB_23      -0.07124
_diffrn_orient_matrix_UB_31      0.043247
_diffrn_orient_matrix_UB_32      -0.061593
_diffrn_orient_matrix_UB_33      -0.042907
_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  0.0655
_diffrn_reflns_av_unetI/netI     0.0747
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6327
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.638
_diffrn_reflns_theta_min         2.329
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.792
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_correction_T_min  0.810
_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    2.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.745
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.14
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1923
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.914
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0439
_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)+(0.0654P)²+0.1321P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.101
_refine_ls_wR_factor_ref         0.1185
_reflns_Friedel_coverage         0
_reflns_number_gt                1281
_reflns_number_total             1923
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj00554k1.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7057104--7057109.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7057105
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
Se01 Se 0.83477(11) 0.71862(4) 0.46838(5) 0.0321(2) Uani 1 1 d . .
Se02 Se 0.71372(13) 1.03520(5) 0.17989(5) 0.0424(2) Uani 1 1 d . .
C3 C 0.5249(10) 0.9026(4) 0.4535(4) 0.0247(12) Uani 1 1 d . .
C2 C 0.6572(10) 0.9836(4) 0.4159(4) 0.0241(11) Uani 1 1 d . .
C4 C 0.8313(10) 0.9712(4) 0.3276(4) 0.0286(13) Uani 1 1 d . .
H4A H 0.8561 0.8993 0.3153 0.034 Uiso 1 1 calc R U
H4B H 0.9915 1.0001 0.3571 0.034 Uiso 1 1 calc R U
N1 N 0.8607(12) 0.7932(5) 0.7090(4) 0.0543(16) Uani 1 1 d . .
C7 C 0.8429(12) 0.7628(4) 0.6168(5) 0.0347(14) Uani 1 1 d . .
C5 C 0.4566(13) 0.9466(6) 0.1418(5) 0.0460(17) Uani 1 1 d . .
C6 C 0.5333(10) 0.7964(4) 0.4087(5) 0.0271(12) Uani 1 1 d . .
H6A H 0.5221 0.7991 0.326 0.033 Uiso 1 1 calc R U
H6B H 0.3883 0.76 0.4275 0.033 Uiso 1 1 calc R U
N2 N 0.2958(13) 0.8904(5) 0.1174(6) 0.073(2) Uani 1 1 d . .
C1 C 0.6291(9) 1.0787(4) 0.4620(4) 0.0246(12) Uani 1 1 d . .
H1 H 0.7163 1.1327 0.4357 0.03 Uiso 1 1 calc R U
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
C7 Se01 C6 95.3(2) . .
C5 Se02 C4 95.3(3) . .
C2 C3 C1 118.1(5) . 3_676
C2 C3 C6 124.3(5) . .
C1 C3 C6 117.6(5) 3_676 .
C1 C2 C3 118.9(5) . .
C1 C2 C4 118.9(5) . .
C3 C2 C4 122.3(5) . .
C2 C4 Se02 114.0(4) . .
C2 C4 H4A 108.7 . .
Se02 C4 H4A 108.7 . .
C2 C4 H4B 108.7 . .
Se02 C4 H4B 108.7 . .
H4A C4 H4B 107.6 . .
N1 C7 Se01 176.1(6) . .
N2 C5 Se02 179.5(7) . .
C3 C6 Se01 114.8(4) . .
C3 C6 H6A 108.6 . .
Se01 C6 H6A 108.6 . .
C3 C6 H6B 108.6 . .
Se01 C6 H6B 108.6 . .
H6A C6 H6B 107.5 . .
C2 C1 C3 123.1(5) . 3_676
C2 C1 H1 118.5 . .
C3 C1 H1 118.5 3_676 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Se01 C7 1.840(6) .
Se01 C6 1.978(5) .
Se02 C5 1.828(8) .
Se02 C4 1.966(5) .
C3 C2 1.390(7) .
C3 C1 1.403(7) 3_676
C3 C6 1.498(7) .
C2 C1 1.382(7) .
C2 C4 1.502(6) .
C4 H4A 0.97 .
C4 H4B 0.97 .
N1 C7 1.151(8) .
C5 N2 1.151(9) .
C6 H6A 0.97 .
C6 H6B 0.97 .
C1 C3 1.403(7) 3_676
C1 H1 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
C1 C3 C2 C1 -0.8(8) 3_676 .
C6 C3 C2 C1 178.4(5) . .
C1 C3 C2 C4 178.6(5) 3_676 .
C6 C3 C2 C4 -2.1(8) . .
C1 C2 C4 Se02 -69.8(6) . .
C3 C2 C4 Se02 110.7(5) . .
C2 C3 C6 Se01 77.5(6) . .
C1 C3 C6 Se01 -103.2(5) 3_676 .
C3 C2 C1 C3 0.9(9) . 3_676
C4 C2 C1 C3 -178.6(5) . 3_676
