#------------------------------------------------------------------------------
#$Date: 2021-02-05 01:24:34 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261720 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/00/7060092.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_7060092
loop_
_publ_author_name
'Huynh, Huu-Tri'
'Jeannin, Olivier'
'Aubert, Emmanuel'
'Espinosa, Enrique'
'Fourmigué, Marc'
_publ_section_title
;
 Chalcogen bonding interactions in chelating, chiral bis(selenocyanates)
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              76
_journal_page_last               84
_journal_paper_doi               10.1039/D0NJ05293K
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C16 H22 Cl0.50 N2.50 Se2'
_chemical_formula_sum            'C16 H22 Cl0.5 N2.5 Se2'
_chemical_formula_weight         425
_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             2020-11-17T09:26:30-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-11-17 deposited with the CCDC.	2020-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.672(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0534(5)
_cell_length_b                   13.1176(6)
_cell_length_c                   16.4261(7)
_cell_measurement_reflns_used    2762
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.9794
_cell_measurement_theta_min      2.4384
_cell_measurement_wavelength     0.71073
_cell_volume                     1800.00(15)
_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 0.997
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_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  0.0365
_diffrn_reflns_av_unetI/netI     0.1411
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4121
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.688
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.179
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.366
_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    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4121
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1583
_refine_ls_R_factor_gt           0.0624
_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)+(0.0756P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1591
_reflns_Friedel_coverage         0
_reflns_number_gt                2069
_reflns_number_total             4121
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj05293k2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7060089--7060096.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C16 H22 Cl0.50 N2.50 Se2'
_cod_database_code               7060092
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 0.9436(7) 0.1570(3) 0.7560(3) 0.0325(12) Uani 1 1 d . . . . .
C2 C 1.1101(7) 0.1548(4) 0.7959(3) 0.0336(12) Uani 1 1 d . . . . .
C3 C 1.1993(8) 0.2180(4) 0.7635(4) 0.0502(16) Uani 1 1 d . . . . .
H3 H 1.3105 0.2169 0.7901 0.06 Uiso 1 1 calc R U . . .
C4 C 1.1247(10) 0.2819(4) 0.6927(4) 0.0571(19) Uani 1 1 d . . . . .
H4 H 1.1862 0.3234 0.6722 0.069 Uiso 1 1 calc R U . . .
C5 C 0.9603(9) 0.2847(4) 0.6522(4) 0.0545(18) Uani 1 1 d . . . . .
H5 H 0.9099 0.3276 0.6044 0.065 Uiso 1 1 calc R U . . .
C6 C 0.8717(8) 0.2219(4) 0.6845(3) 0.0434(15) Uani 1 1 d . . . . .
H6 H 0.7606 0.2232 0.6574 0.052 Uiso 1 1 calc R U . . .
C7 C 0.8374(7) 0.0915(4) 0.7869(3) 0.0443(15) Uani 1 1 d . . . . .
H7 H 0.9033 0.0333 0.8176 0.053 Uiso 1 1 calc R U . . .
C8 C 0.6892(8) 0.0464(5) 0.7158(4) 0.0613(18) Uani 1 1 d . . . . .
H8A H 0.6175 0.1003 0.6854 0.092 Uiso 1 1 calc R U . . .
H8B H 0.6368 0.0016 0.7424 0.092 Uiso 1 1 calc R U . . .
H8C H 0.7198 0.0088 0.6746 0.092 Uiso 1 1 calc R U . . .
C9 C 0.6405(9) 0.2541(5) 0.7965(5) 0.0600(18) Uani 1 1 d . . . . .
C10 C 1.2002(7) 0.0836(4) 0.8712(3) 0.0401(14) Uani 1 1 d . . . . .
H10 H 1.1238 0.0302 0.8701 0.048 Uiso 1 1 calc R U . . .
C11 C 1.3428(8) 0.0286(5) 0.8650(4) 0.0602(18) Uani 1 1 d . . . . .
H11A H 1.3092 -0.009 0.8107 0.09 Uiso 1 1 calc R U . . .
H11B H 1.3867 -0.0175 0.9139 0.09 Uiso 1 1 calc R U . . .
H11C H 1.4228 0.0775 0.8666 0.09 Uiso 1 1 calc R U . . .
C12 C 1.4222(10) 0.2342(6) 0.9787(4) 0.067(2) Uani 1 1 d . . . . .
C13 C 0.9808(17) 0.4910(9) 1.0857(7) 0.054(4) Uani 0.5 1 d . . P A -1
H13A H 0.8713 0.4699 1.0724 0.065 Uiso 0.5 1 calc R U P A -1
H13B H 1.0488 0.4352 1.1177 0.065 Uiso 0.5 1 calc R U P A -1
C17A C 1.012(3) 0.5745(17) 1.1455(17) 0.043(5) Uani 0.5 1 d . U P A -1
H17A H 0.9932 0.554 1.1967 0.065 Uiso 0.5 1 calc R U P A -1
H17B H 1.1217 0.5954 1.1629 0.065 Uiso 0.5 1 calc R U P A -1
H17C H 0.9429 0.6304 1.1172 0.065 Uiso 0.5 1 calc R U P A -1
C15 C 1.1724(16) 0.5524(9) 1.0213(8) 0.056(3) Uani 0.5 1 d . . P A -1
H15A H 1.1821 0.5689 0.966 0.067 Uiso 0.5 1 calc R U P A -1
H15B H 1.1768 0.616 1.0524 0.067 Uiso 0.5 1 calc R U P A -1
C18A C 1.309(3) 0.4895(17) 1.074(2) 0.086(7) Uani 0.5 1 d . U P A -1
H18A H 1.4066 0.5257 1.084 0.129 Uiso 0.5 1 calc R U P A -1
H18B H 1.3025 0.4743 1.1298 0.129 Uiso 0.5 1 calc R U P A -1
H18C H 1.3078 0.4271 1.0433 0.129 Uiso 0.5 1 calc R U P A -1
C14 C 1.0159(15) 0.5920(8) 1.0454(6) 0.040(3) Uani 0.5 1 d . . P A -2
H14A H 0.9512 0.6421 1.0033 0.049 Uiso 0.5 1 calc R U P A -2
H14B H 1.1265 0.6134 1.0633 0.049 Uiso 0.5 1 calc R U P A -2
C16 C 1.1099(17) 0.4114(9) 1.0547(7) 0.056(3) Uani 0.5 1 d . . P A -2
H16A H 1.0837 0.3963 1.1054 0.067 Uiso 0.5 1 calc R U P A -2
H16B H 1.0901 0.3505 1.0185 0.067 Uiso 0.5 1 calc R U P A -2
C17B C 0.973(3) 0.5993(17) 1.1269(15) 0.039(5) Uani 0.5 1 d . U P A -2
H17D H 0.9915 0.6677 1.1495 0.059 Uiso 0.5 1 calc R U P A -2
H17E H 0.8628 0.5819 1.1109 0.059 Uiso 0.5 1 calc R U P A -2
H17F H 1.0393 0.5531 1.1713 0.059 Uiso 0.5 1 calc R U P A -2
C18B C 1.279(3) 0.439(2) 1.085(2) 0.099(9) Uani 0.5 1 d . U P A -2
H18D H 1.3431 0.3833 1.1178 0.149 Uiso 0.5 1 calc R U P A -2
H18E H 1.3052 0.4526 1.0345 0.149 Uiso 0.5 1 calc R U P A -2
H18F H 1.2989 0.4983 1.1213 0.149 Uiso 0.5 1 calc R U P A -2
N1 N 0.5569(9) 0.3131(5) 0.7498(5) 0.093(2) Uani 1 1 d . . . . .
N2 N 1.5228(10) 0.2849(6) 0.9776(4) 0.105(3) Uani 1 1 d . . . . .
N3 N 1 0.5 1 0.0396(16) Uani 1 2 d S . P . .
Cl1 Cl 1 0 1 0.0596(7) Uani 1 2 d S . P . .
Se1 Se 0.77372(8) 0.16239(4) 0.87611(4) 0.0506(2) Uani 1 1 d . . . . .
Se2 Se 1.26263(8) 0.15187(5) 0.98892(4) 0.0543(2) 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'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 118.6(5) . . ?
C6 C1 C7 118.6(5) . . ?
C2 C1 C7 122.8(5) . . ?
C1 C2 C3 119.2(5) . . ?
C1 C2 C10 122.8(5) . . ?
C3 C2 C10 117.9(5) . . ?
C4 C3 C2 120.9(6) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 120.7(6) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 118.4(6) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 122.2(6) . . ?
C5 C6 H6 118.9 . . ?
C1 C6 H6 118.9 . . ?
C1 C7 C8 116.7(4) . . ?
C1 C7 Se1 112.4(3) . . ?
C8 C7 Se1 109.1(4) . . ?
C1 C7 H7 106 . . ?
C8 C7 H7 106 . . ?
Se1 C7 H7 106 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 Se1 177.2(7) . . ?
C2 C10 C11 116.3(5) . . ?
C2 C10 Se2 112.0(3) . . ?
C11 C10 Se2 110.3(4) . . ?
C2 C10 H10 105.8 . . ?
C11 C10 H10 105.8 . . ?
Se2 C10 H10 105.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 Se2 176.1(7) . . ?
C17A C13 N3 121.8(13) . . ?
C17A C13 H13A 106.9 . . ?
N3 C13 H13A 106.9 . . ?
C17A C13 H13B 106.9 . . ?
N3 C13 H13B 106.9 . . ?
H13A C13 H13B 106.7 . . ?
C13 C17A H17A 109.5 . . ?
C13 C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C13 C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C18A C15 N3 114.4(11) . . ?
C18A C15 H15A 108.6 . . ?
N3 C15 H15A 108.6 . . ?
C18A C15 H15B 108.6 . . ?
N3 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C15 C18A H18A 109.5 . . ?
C15 C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C15 C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
N3 C14 C17B 120.8(12) . . ?
N3 C14 H14A 107.1 . . ?
C17B C14 H14A 107.1 . . ?
N3 C14 H14B 107.1 . . ?
C17B C14 H14B 107.1 . . ?
H14A C14 H14B 106.8 . . ?
C18B C16 N3 111.2(14) . . ?
C18B C16 H16A 109.4 . . ?
N3 C16 H16A 109.4 . . ?
C18B C16 H16B 109.4 . . ?
N3 C16 H16B 109.4 . . ?
H16A C16 H16B 108 . . ?
C14 C17B H17D 109.5 . . ?
C14 C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C14 C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C16 C18B H18D 109.5 . . ?
C16 C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C16 C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C14 N3 C16 115.0(6) . . ?
C13 N3 C15 106.5(7) . . ?
C9 Se1 C7 94.5(3) . . ?
C12 Se2 C10 96.5(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 C6 1.392(7) . ?
C1 C2 1.393(8) . ?
C1 C7 1.516(7) . ?
C2 C3 1.397(7) . ?
C2 C10 1.513(7) . ?
C3 C4 1.381(8) . ?
C3 H3 0.93 . ?
C4 C5 1.377(9) . ?
C4 H4 0.93 . ?
C5 C6 1.390(8) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.518(7) . ?
C7 Se1 2.000(5) . ?
C7 H7 0.98 . ?
C8 H8A 0.96 . ?
C8 H8B 0.96 . ?
C8 H8C 0.96 . ?
C9 N1 1.145(8) . ?
C9 Se1 1.843(8) . ?
C10 C11 1.516(8) . ?
C10 Se2 2.005(5) . ?
C10 H10 0.98 . ?
C11 H11A 0.96 . ?
C11 H11B 0.96 . ?
C11 H11C 0.96 . ?
C12 N2 1.134(9) . ?
C12 Se2 1.862(9) . ?
C13 C17A 1.42(3) . ?
C13 N3 1.488(10) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C17A H17A 0.96 . ?
C17A H17B 0.96 . ?
C17A H17C 0.96 . ?
C15 C18A 1.46(3) . ?
C15 N3 1.616(13) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C18A H18A 0.96 . ?
C18A H18B 0.96 . ?
C18A H18C 0.96 . ?
C14 N3 1.397(10) . ?
C14 C17B 1.53(3) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C16 C18B 1.46(3) . ?
C16 N3 1.568(11) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C17B H17D 0.96 . ?
C17B H17E 0.96 . ?
C17B H17F 0.96 . ?
C18B H18D 0.96 . ?
C18B H18E 0.96 . ?
C18B H18F 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.5(7) . . . . ?
C7 C1 C2 C3 -179.8(4) . . . . ?
C6 C1 C2 C10 -177.0(4) . . . . ?
C7 C1 C2 C10 2.7(7) . . . . ?
C1 C2 C3 C4 -0.2(8) . . . . ?
C10 C2 C3 C4 177.4(5) . . . . ?
C2 C3 C4 C5 -0.1(9) . . . . ?
C3 C4 C5 C6 0.1(8) . . . . ?
C4 C5 C6 C1 0.2(8) . . . . ?
C2 C1 C6 C5 -0.5(7) . . . . ?
C7 C1 C6 C5 179.8(5) . . . . ?
C6 C1 C7 C8 38.5(7) . . . . ?
C2 C1 C7 C8 -141.2(5) . . . . ?
C6 C1 C7 Se1 -88.5(5) . . . . ?
C2 C1 C7 Se1 91.7(5) . . . . ?
C1 C2 C10 C11 135.0(6) . . . . ?
C3 C2 C10 C11 -42.5(7) . . . . ?
C1 C2 C10 Se2 -96.9(5) . . . . ?
C3 C2 C10 Se2 85.6(5) . . . . ?
C17B C14 N3 C16 -63.1(15) . . . . ?
C17A C13 N3 C15 48.0(16) . . . . ?
C18B C16 N3 C14 -59.8(17) . . . . ?
C18A C15 N3 C13 66.9(16) . . . . ?
