#------------------------------------------------------------------------------
#$Date: 2019-11-24 05:16:59 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236811 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/70/7237084.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_7237084
loop_
_publ_author_name
'Kumar, Vijith'
'Leroy, César'
'Bryce, David L.'
_publ_section_title
;
 Halide ion recognition via chalcogen bonding in the solid state and in
 solution. Directionality and linearity
;
_journal_issue                   41
_journal_name_full               CrystEngComm
_journal_page_first              6406
_journal_paper_doi               10.1039/C8CE01365A
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C16 H36 N, C10 H8 N2 Se2,Cl'
_chemical_formula_sum            'C26 H44 Cl N3 Se2'
_chemical_formula_weight         592.01
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-I 2y'
_space_group_name_H-M_alt        'I 1 2/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-09-10 deposited with the CCDC.
2018-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.041(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5130(13)
_cell_length_b                   14.1548(18)
_cell_length_c                   17.6517(18)
_cell_measurement_reflns_used    8754
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.20
_cell_volume                     3068.6(6)
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_collection       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_molecular_graphics
'Olex2 (Dolomanov et al., 2009), Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1727
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            73740
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_min         1.840
_exptl_absorpt_coefficient_mu    2.514
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4234
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.994
_refine_diff_density_min         -0.853
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2901
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.174
_refine_ls_R_factor_all          0.1513
_refine_ls_R_factor_gt           0.0909
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+63.1347P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1968
_refine_ls_wR_factor_ref         0.2367
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1713
_reflns_number_total             2901
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce01365a2.cif
_cod_data_source_block           shelx_CCDC1
_cod_original_sg_symbol_H-M      'I 2/m'
_cod_database_code               7237084
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.572
_shelx_estimated_absorpt_t_max   0.752
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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
N2 N 0.4546(9) 0.000000 0.3013(6) 0.062(3) Uani 1 2 d S T P . .
C6 C 0.4150(13) 0.000000 0.3797(7) 0.065(4) Uani 1 2 d S T P . .
H6A H 0.445025 -0.056420 0.409450 0.078 Uiso 0.5 1 d R U P . .
H6B H 0.445025 0.056420 0.409440 0.078 Uiso 0.5 1 d R U P . .
C7 C 0.2934(14) 0.000000 0.3725(9) 0.089(6) Uani 1 2 d DS T P . .
H7A H 0.261476 -0.056773 0.344108 0.107 Uiso 0.5 1 calc R U P . .
H7B H 0.261476 0.056773 0.344108 0.107 Uiso 0.5 1 calc R U P . .
C8 C 0.2696(13) 0.000000 0.4548(9) 0.083(5) Uani 1 2 d DS T P . .
H8A H 0.302445 -0.056654 0.482921 0.099 Uiso 0.5 1 calc R U P . .
H8B H 0.302445 0.056654 0.482921 0.099 Uiso 0.5 1 calc R U P . .
C9 C 0.1521(15) 0.000000 0.4515(13) 0.130(9) Uani 1 2 d DS T P . .
H9A H 0.137389 0.000000 0.504099 0.156 Uiso 1 2 calc R U P . .
H9B H 0.120066 0.056530 0.424163 0.156 Uiso 0.5 1 calc R U P . .
H9C H 0.120066 -0.056530 0.424163 0.156 Uiso 0.5 1 calc R U P . .
C10 C 0.4141(8) 0.0871(9) 0.2540(5) 0.071(3) Uani 1 1 d . . . . .
H10A H 0.440635 0.083895 0.204739 0.085 Uiso 1 1 calc R U . . .
H10B H 0.333549 0.084635 0.241383 0.085 Uiso 1 1 calc R U . . .
C11 C 0.4468(12) 0.1792(10) 0.2907(7) 0.097(4) Uani 1 1 d D . . . .
H11A H 0.422385 0.182237 0.340819 0.117 Uiso 1 1 calc R U . . .
H11B H 0.527234 0.183443 0.301395 0.117 Uiso 1 1 calc R U . . .
C12 C 0.4019(10) 0.2613(11) 0.2434(7) 0.093(4) Uani 1 1 d D . . . .
H12A H 0.429090 0.259699 0.194303 0.111 Uiso 1 1 calc R U . . .
H12B H 0.321656 0.255301 0.230650 0.111 Uiso 1 1 calc R U . . .
C13 C 0.4295(16) 0.3526(12) 0.2804(10) 0.140(7) Uani 1 1 d D . . . .
H13A H 0.396979 0.403240 0.245564 0.211 Uiso 1 1 calc R U . . .
H13B H 0.401194 0.355774 0.328369 0.211 Uiso 1 1 calc R U . . .
H13C H 0.508796 0.360180 0.291965 0.211 Uiso 1 1 calc R U . . .
C14 C 0.5797(11) 0.000000 0.3210(9) 0.076(5) Uani 1 2 d S T P A .
H14A H 0.604623 0.056490 0.352538 0.091 Uiso 0.5 1 calc R U P . .
H14B H 0.604623 -0.056490 0.352538 0.091 Uiso 0.5 1 calc R U P . .
C15 C 0.6311(13) 0.000000 0.2514(11) 0.098(6) Uani 1 2 d DS T P . .
H15A H 0.621589 0.062281 0.225455 0.117 Uiso 0.5 1 calc R U P A .
H15B H 0.597416 -0.048922 0.214316 0.117 Uiso 0.5 1 calc R U P . .
C16 C 0.7577(18) -0.022(3) 0.2808(16) 0.112(14) Uani 0.5 1 d D . P A -1
H16A H 0.782172 0.001670 0.334031 0.135 Uiso 0.5 1 calc R U P A -1
H16B H 0.771120 -0.090960 0.280353 0.135 Uiso 0.5 1 calc R U P A -1
C17 C 0.816(2) 0.026(4) 0.228(2) 0.20(2) Uani 0.5 1 d D U P A -1
H17A H 0.894148 0.014342 0.243758 0.304 Uiso 0.5 1 calc R U P A -1
H17B H 0.790750 0.001822 0.175469 0.304 Uiso 0.5 1 calc R U P A -1
H17C H 0.801748 0.094008 0.228889 0.304 Uiso 0.5 1 calc R U P A -1
Se1 Se 0.21383(10) 0.25357(11) -0.06965(7) 0.0832(5) Uani 1 1 d . . . . .
N1 N 0.4190(13) 0.2097(13) -0.1204(8) 0.158(7) Uani 1 1 d . . . . .
C1 C 0.1674(8) 0.0466(8) 0.0305(7) 0.081(4) Uani 1 1 d . . . . .
H1 H 0.100658 0.079679 0.027477 0.097 Uiso 1 1 calc R U . . .
C2 C 0.2653(8) 0.0979(9) 0.0349(5) 0.061(3) Uani 1 1 d . . . . .
C3 C 0.3615(7) 0.0479(7) 0.0402(5) 0.060(3) Uani 1 1 d . . . . .
H3 H 0.428257 0.081068 0.043856 0.073 Uiso 1 1 calc R U . . .
C4 C 0.2636(9) 0.2000(10) 0.0344(6) 0.077(3) Uani 1 1 d . . . . .
H4A H 0.337802 0.223718 0.055453 0.092 Uiso 1 1 calc R U . . .
H4B H 0.214897 0.222293 0.068723 0.092 Uiso 1 1 calc R U . . .
C5 C 0.3419(12) 0.2292(11) -0.0999(7) 0.096(4) Uani 1 1 d . . . . .
Cl1 Cl 0.500000 0.2109(3) 0.500000 0.0711(11) Uani 1 2 d S T P . .
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 0.0000 0.0000 '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'
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
C10 N2 C10 108.3(11) 6 .
C10 N2 C14 110.0(7) 6 .
C10 N2 C14 110.0(7) . .
C10 N2 C6 111.0(7) 6 .
C10 N2 C6 111.0(7) . .
C14 N2 C6 106.5(11) . .
C7 C6 N2 114.5(11) . .
C7 C6 H6A 108.7 . .
N2 C6 H6A 108.6 . .
C7 C6 H6B 108.7 . .
N2 C6 H6B 108.6 . .
H6A C6 H6B 107.6 . .
C6 C7 C8 107.3(13) . .
C6 C7 H7A 110.3 . .
C8 C7 H7A 110.3 . .
C6 C7 H7B 110.3 . .
C8 C7 H7B 110.3 . .
H7A C7 H7B 108.5 . .
C9 C8 C7 109.8(15) . .
C9 C8 H8A 109.7 . .
C7 C8 H8A 109.7 . .
C9 C8 H8B 109.7 . .
C7 C8 H8B 109.7 . .
H8A C8 H8B 108.2 . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C11 C10 N2 116.1(8) . .
C11 C10 H10A 108.3 . .
N2 C10 H10A 108.3 . .
C11 C10 H10B 108.3 . .
N2 C10 H10B 108.3 . .
H10A C10 H10B 107.4 . .
C12 C11 C10 113.7(11) . .
C12 C11 H11A 108.8 . .
C10 C11 H11A 108.8 . .
C12 C11 H11B 108.8 . .
C10 C11 H11B 108.8 . .
H11A C11 H11B 107.7 . .
C13 C12 C11 114.3(12) . .
C13 C12 H12A 108.7 . .
C11 C12 H12A 108.7 . .
C13 C12 H12B 108.7 . .
C11 C12 H12B 108.7 . .
H12A C12 H12B 107.6 . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C15 C14 N2 113.3(12) . .
C15 C14 H14A 108.9 . .
N2 C14 H14A 108.9 . .
C15 C14 H14B 108.9 . .
N2 C14 H14B 108.9 . .
H14A C14 H14B 107.7 . .
C14 C15 C16 106.8(16) . .
C14 C15 H15A 110.4 . .
C16 C15 H15A 110.4 . .
C14 C15 H15B 110.4 . .
C16 C15 H15B 110.4 . .
H15A C15 H15B 108.6 . .
C14 C15 H15A 110.4(3) . 6
C16 C15 H15A 90.0(15) . 6
H15A C15 H15A 125.9 . 6
H15B C15 H15A 22.0 . 6
C14 C15 H15B 110.4(6) . 6
C16 C15 H15B 128.4(13) . 6
H15A C15 H15B 22.0 . 6
H15B C15 H15B 88.8 . 6
H15A C15 H15B 108.6 6 6
C17 C16 C15 107(2) . .
C17 C16 H16A 110.4 . .
C15 C16 H16A 110.4 . .
C17 C16 H16B 110.4 . .
C15 C16 H16B 110.4 . .
H16A C16 H16B 108.6 . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C5 Se1 C4 93.5(5) . .
C1 C1 C2 120.9(7) 6 .
C1 C1 H1 119.6 6 .
C2 C1 H1 119.6 . .
C3 C2 C1 118.4(11) . .
C3 C2 C4 121.6(10) . .
C1 C2 C4 120.1(10) . .
C3 C3 C2 120.8(7) 6 .
C3 C3 H3 119.6 6 .
C2 C3 H3 119.6 . .
C2 C4 Se1 113.1(8) . .
C2 C4 H4A 109.0 . .
Se1 C4 H4A 109.0 . .
C2 C4 H4B 109.0 . .
Se1 C4 H4B 109.0 . .
H4A C4 H4B 107.8 . .
N1 C5 Se1 176.3(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N2 C10 1.520(12) 6
N2 C10 1.520(12) .
N2 C14 1.538(18) .
N2 C6 1.555(16) .
C6 C7 1.50(2) .
C6 H6A 0.9900 .
C6 H6B 0.9899 .
C7 C8 1.537(19) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C9 1.461(18) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 C11 1.479(17) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.477(16) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.459(17) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 C15 1.49(2) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.60(3) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C15 H15A 0.9900 6
C15 H15B 0.9900 6
C16 C17 1.46(2) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
Se1 C5 1.816(14) .
Se1 C4 1.974(11) .
N1 C5 1.128(16) .
C1 C1 1.32(2) 6
C1 C2 1.414(14) .
C1 H1 0.9500 .
C2 C3 1.383(13) .
C2 C4 1.446(16) .
C3 C3 1.36(2) 6
C3 H3 0.9500 .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
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
C10 N2 C6 C7 -60.3(7) 6 .
C10 N2 C6 C7 60.3(7) . .
C14 N2 C6 C7 180.000(2) . .
N2 C6 C7 C8 180.000(3) . .
C6 C7 C8 C9 180.000(4) . .
C10 N2 C10 C11 -179.4(8) 6 .
C14 N2 C10 C11 -59.1(13) . .
C6 N2 C10 C11 58.5(13) . .
N2 C10 C11 C12 -177.9(11) . .
C10 C11 C12 C13 177.4(14) . .
C10 N2 C14 C15 59.6(7) 6 .
C10 N2 C14 C15 -59.6(7) . .
C6 N2 C14 C15 180.000(2) . .
N2 C14 C15 C16 -168.2(16) . .
C14 C15 C16 C17 -150(3) . .
C1 C1 C2 C3 -0.8(11) 6 .
C1 C1 C2 C4 179.6(7) 6 .
C1 C2 C3 C3 0.8(11) . 6
C4 C2 C3 C3 -179.7(7) . 6
C3 C2 C4 Se1 102.5(10) . .
C1 C2 C4 Se1 -77.9(11) . .
