#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:04:42 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230369 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/71/7057108.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_7057108
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, 2(C3 H7 N O)'
_chemical_formula_sum            'C20 H24 N6 O2 Se4'
_chemical_formula_weight         696.29
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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             2018-01-18T14:29:44-00:00
_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                108.086(15)
_cell_angle_beta                 116.283(14)
_cell_angle_gamma                102.687(15)
_cell_formula_units_Z            1
_cell_length_a                   9.224(5)
_cell_length_b                   9.382(5)
_cell_length_c                   9.591(5)
_cell_measurement_reflns_used    4824
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.68
_cell_measurement_wavelength     0.71073
_cell_volume                     642.3(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 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_UB_11      -0.127599
_diffrn_orient_matrix_UB_12      -0.021674
_diffrn_orient_matrix_UB_13      -0.046229
_diffrn_orient_matrix_UB_21      -0.037968
_diffrn_orient_matrix_UB_22      -0.103695
_diffrn_orient_matrix_UB_23      -0.103763
_diffrn_orient_matrix_UB_31      -0.002946
_diffrn_orient_matrix_UB_32      -0.063468
_diffrn_orient_matrix_UB_33      0.066119
_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  0.0519
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14597
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_min         2.515
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.74
_exptl_absorpt_correction_T_max  0.532
_exptl_absorpt_correction_T_min  0.184
_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    1.8
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             338
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.891
_refine_diff_density_min         -0.94
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.04
_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)+(0.0299P)²+0.8650P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0905
_reflns_Friedel_coverage         0
_reflns_number_gt                2248
_reflns_number_total             2942
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj00554k1.cif
_cod_data_source_block           2-DMF2
_cod_depositor_comments
'Adding full bibliography for 7057104--7057109.cif.'
_cod_database_code               7057108
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 0.4060(5) 0.0004(4) 0.8377(4) 0.0257(7) Uani 1 1 d . .
C2 C 0.5924(5) 0.0729(4) 0.9381(5) 0.0245(7) Uani 1 1 d . .
C3 C 0.6806(5) 0.0703(4) 1.0975(5) 0.0269(8) Uani 1 1 d . .
H3 H 0.8045 0.1186 1.1645 0.032 Uiso 1 1 calc R U
C4 C 0.2964(5) -0.0054(5) 0.6642(5) 0.0315(8) Uani 1 1 d . .
H4A H 0.1837 -0.1018 0.594 0.038 Uiso 1 1 calc R U
H4B H 0.3572 -0.0189 0.6037 0.038 Uiso 1 1 calc R U
C5 C 0.7000(5) 0.1479(5) 0.8791(5) 0.0330(9) Uani 1 1 d . .
H5A H 0.6379 0.0842 0.7526 0.04 Uiso 1 1 calc R U
H5B H 0.813 0.1397 0.9318 0.04 Uiso 1 1 calc R U
C6 C 0.1140(6) 0.1623(5) 0.7724(5) 0.0384(9) Uani 1 1 d . .
C7 C 0.9003(6) 0.4655(6) 1.1771(7) 0.0507(12) Uani 1 1 d . .
C8 C 0.4529(6) -0.2824(5) 0.5139(6) 0.0412(10) Uani 1 1 d . .
H8 H 0.3318 -0.3174 0.4686 0.049 Uiso 1 1 calc R U
C9 C 0.4712(8) -0.3758(6) 0.7264(7) 0.0577(13) Uani 1 1 d . .
H9A H 0.5285 -0.2994 0.848 0.087 Uiso 1 1 calc R U
H9B H 0.486 -0.4758 0.7171 0.087 Uiso 1 1 calc R U
H9C H 0.3465 -0.4003 0.6648 0.087 Uiso 1 1 calc R U
C10 C 0.7387(7) -0.2522(7) 0.7264(7) 0.0634(14) Uani 1 1 d . .
H10A H 0.764 -0.3478 0.7043 0.095 Uiso 1 1 calc R U
H10B H 0.8021 -0.1833 0.8508 0.095 Uiso 1 1 calc R U
H10C H 0.7756 -0.1915 0.675 0.095 Uiso 1 1 calc R U
N1 N 0.0331(6) 0.1479(6) 0.8307(6) 0.0645(12) Uani 1 1 d . .
N2 N 0.9947(7) 0.5246(7) 1.3253(7) 0.0848(16) Uani 1 1 d . .
N3 N 0.5505(5) -0.3032(4) 0.6499(4) 0.0403(8) Uani 1 1 d . .
O1 O 0.5093(4) -0.2206(4) 0.4430(4) 0.0547(8) Uani 1 1 d . .
Se1 Se 0.24801(5) 0.19258(5) 0.67846(5) 0.03601(13) Uani 1 1 d . .
Se2 Se 0.74703(6) 0.38161(5) 0.93915(6) 0.04390(15) 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'
O O 0.0106 0.006 '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
C3 C1 C2 118.3(3) 2_657
C3 C1 C4 118.5(3) 2_657
C2 C1 C4 123.1(3) .
C3 C2 C1 118.1(3) .
C3 C2 C5 118.8(3) .
C1 C2 C5 123.1(3) .
C1 C3 C2 123.6(3) 2_657
C1 C3 H3 118.2 2_657
C2 C3 H3 118.2 .
C1 C4 Se1 114.5(3) .
C1 C4 H4A 108.6 .
Se1 C4 H4A 108.6 .
C1 C4 H4B 108.6 .
Se1 C4 H4B 108.6 .
H4A C4 H4B 107.6 .
C2 C5 Se2 114.3(3) .
C2 C5 H5A 108.7 .
Se2 C5 H5A 108.7 .
C2 C5 H5B 108.7 .
Se2 C5 H5B 108.7 .
H5A C5 H5B 107.6 .
N1 C6 Se1 178.2(4) .
N2 C7 Se2 176.6(5) .
O1 C8 N3 125.1(4) .
O1 C8 H8 117.4 .
N3 C8 H8 117.4 .
N3 C9 H9A 109.5 .
N3 C9 H9B 109.5 .
H9A C9 H9B 109.5 .
N3 C9 H9C 109.5 .
H9A C9 H9C 109.5 .
H9B C9 H9C 109.5 .
N3 C10 H10A 109.5 .
N3 C10 H10B 109.5 .
H10A C10 H10B 109.5 .
N3 C10 H10C 109.5 .
H10A C10 H10C 109.5 .
H10B C10 H10C 109.5 .
C8 N3 C10 120.4(4) .
C8 N3 C9 120.9(4) .
C10 N3 C9 118.7(4) .
C6 Se1 C4 95.76(17) .
C7 Se2 C5 96.39(19) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C3 1.388(5) 2_657
C1 C2 1.399(5) .
C1 C4 1.491(5) .
C2 C3 1.389(5) .
C2 C5 1.497(5) .
C3 C1 1.388(5) 2_657
C3 H3 0.93 .
C4 Se1 1.982(4) .
C4 H4A 0.97 .
C4 H4B 0.97 .
C5 Se2 1.976(4) .
C5 H5A 0.97 .
C5 H5B 0.97 .
C6 N1 1.123(5) .
C6 Se1 1.847(4) .
C7 N2 1.135(6) .
C7 Se2 1.835(5) .
C8 O1 1.223(5) .
C8 N3 1.320(5) .
C8 H8 0.93 .
C9 N3 1.451(5) .
C9 H9A 0.96 .
C9 H9B 0.96 .
C9 H9C 0.96 .
C10 N3 1.439(6) .
C10 H10A 0.96 .
C10 H10B 0.96 .
C10 H10C 0.96 .
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 -0.1(6) 2_657 .
C4 C1 C2 C3 -179.7(3) . .
C3 C1 C2 C5 178.0(3) 2_657 .
C4 C1 C2 C5 -1.5(5) . .
C1 C2 C3 C1 0.1(6) . 2_657
C5 C2 C3 C1 -178.1(3) . 2_657
C3 C1 C4 Se1 93.8(4) 2_657 .
C2 C1 C4 Se1 -86.7(4) . .
C3 C2 C5 Se2 -95.3(4) . .
C1 C2 C5 Se2 86.6(4) . .
O1 C8 N3 C10 -0.2(7) . .
O1 C8 N3 C9 179.1(4) . .
