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#$Date: 2016-04-05 20:16:11 +0300 (Tue, 05 Apr 2016) $
#$Revision: 181711 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/73/7037381.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_7037381
loop_
_publ_author_name
'Karhu, Aino J.'
'Pakkanen, Olli J.'
'Rautiainen, J. Mikko'
'Oilunkaniemi, Raija'
'Chivers, Tristram'
'Laitinen, Risto S.'
_publ_section_title
;
 The role of imidoselenium(ii) chlorides in the formation of cyclic
 selenium imides via cyclocondensation.
;
_journal_issue                   14
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              6210
_journal_page_last               6221
_journal_paper_doi               10.1039/c5dt04236d
_journal_volume                  45
_journal_year                    2016
_chemical_formula_sum            'C12 H27 Cl2 N3 Se4'
_chemical_formula_weight         600.10
_chemical_name_systematic
2,4,6-tris(tert-butyl)-1,7-dichlorido-2,4,6-triazy-1,3,5,7-triseleny-[7]catena
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-10-27 deposited with the CCDC.
2015-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.96(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.390(3)
_cell_length_b                   10.575(2)
_cell_length_c                   16.502(3)
_cell_measurement_reflns_used    3304
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.998
_cell_measurement_theta_min      3.277
_cell_volume                     2068.1(8)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Bruker, 2008)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker Nonius Kappaccd'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8089
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.277
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    7.352
_exptl_absorpt_correction_T_max  0.97563
_exptl_absorpt_correction_T_min  0.60155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'XPREP in SHELXTL (Sheldrick 2008)'
_exptl_crystal_colour            red-brown
_exptl_crystal_density_diffrn    1.927
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       0.0031(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3891
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0400
_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)+(0.0299P)²+8.4779P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0940
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3304
_reflns_number_total             3891
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5dt04236d2.cif
_cod_data_source_block           cmpd9a
_cod_depositor_comments
'Adding full bibliography for 7037381--7037383.cif.'
_cod_original_cell_volume        2068.0(8)
_cod_database_code               7037381
_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   0.157
_shelx_estimated_absorpt_t_max   0.321
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'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
Se1 Se 0.09460(4) 0.21568(5) 0.49343(3) 0.02351(16) Uani 1 1 d . .
Se2 Se 0.33454(4) 0.32172(5) 0.50245(3) 0.02103(15) Uani 1 1 d . .
Se3 Se 0.13672(4) 0.50183(5) 0.42180(3) 0.01976(15) Uani 1 1 d . .
Se4 Se 0.08857(5) 0.77948(5) 0.37309(3) 0.02523(16) Uani 1 1 d . .
Cl11 Cl 0.05680(13) 0.12272(16) 0.36374(9) 0.0402(4) Uani 1 1 d . .
Cl41 Cl -0.08120(12) 0.70855(14) 0.29445(9) 0.0344(3) Uani 1 1 d . .
N1 N 0.2406(4) 0.2043(4) 0.5412(3) 0.0206(9) Uani 1 1 d . .
N2 N 0.2600(4) 0.4650(4) 0.5122(3) 0.0212(9) Uani 1 1 d . .
N3 N 0.1837(3) 0.6508(4) 0.3764(3) 0.0204(9) Uani 1 1 d . .
C10 C 0.3006(5) 0.0856(5) 0.5828(4) 0.0267(12) Uani 1 1 d . .
C11 C 0.3632(7) 0.0251(6) 0.5253(5) 0.0521(19) Uani 1 1 d . .
H11A H 0.3094 0.0052 0.4703 0.078 Uiso 1 1 calc R U
H11B H 0.4002 -0.0529 0.5516 0.078 Uiso 1 1 calc R U
H11C H 0.4202 0.0841 0.5173 0.078 Uiso 1 1 calc R U
C12 C 0.2143(5) -0.0080(5) 0.5978(4) 0.0365(14) Uani 1 1 d . .
H12A H 0.1735 0.0312 0.6340 0.055 Uiso 1 1 calc R U
H12B H 0.2534 -0.0840 0.6257 0.055 Uiso 1 1 calc R U
H12C H 0.1608 -0.0314 0.5434 0.055 Uiso 1 1 calc R U
C13 C 0.3807(5) 0.1241(6) 0.6678(4) 0.0418(16) Uani 1 1 d . .
H13A H 0.4355 0.1853 0.6588 0.063 Uiso 1 1 calc R U
H13B H 0.4206 0.0493 0.6967 0.063 Uiso 1 1 calc R U
H13C H 0.3378 0.1627 0.7027 0.063 Uiso 1 1 calc R U
C20 C 0.2961(4) 0.5485(5) 0.5898(3) 0.0220(11) Uani 1 1 d . .
C21 C 0.3844(4) 0.6396(5) 0.5777(4) 0.0270(12) Uani 1 1 d . .
H21A H 0.4481 0.5918 0.5693 0.041 Uiso 1 1 calc R U
H21B H 0.4110 0.6932 0.6280 0.041 Uiso 1 1 calc R U
H21C H 0.3514 0.6926 0.5279 0.041 Uiso 1 1 calc R U
C22 C 0.3436(5) 0.4683(5) 0.6688(3) 0.0305(13) Uani 1 1 d . .
H22A H 0.4109 0.4234 0.6646 0.046 Uiso 1 1 calc R U
H22B H 0.2866 0.4070 0.6738 0.046 Uiso 1 1 calc R U
H22C H 0.3638 0.5231 0.7189 0.046 Uiso 1 1 calc R U
C23 C 0.1942(5) 0.6210(5) 0.5996(4) 0.0287(12) Uani 1 1 d . .
H23A H 0.2173 0.6738 0.6506 0.043 Uiso 1 1 calc R U
H23B H 0.1362 0.5610 0.6047 0.043 Uiso 1 1 calc R U
H23C H 0.1635 0.6749 0.5498 0.043 Uiso 1 1 calc R U
C30 C 0.2452(4) 0.6421(5) 0.3094(3) 0.0244(11) Uani 1 1 d . .
C31 C 0.3042(5) 0.7679(6) 0.3076(4) 0.0378(15) Uani 1 1 d . .
H31A H 0.2478 0.8353 0.2913 0.057 Uiso 1 1 calc R U
H31B H 0.3472 0.7635 0.2664 0.057 Uiso 1 1 calc R U
H31C H 0.3556 0.7858 0.3640 0.057 Uiso 1 1 calc R U
C32 C 0.3341(5) 0.5394(5) 0.3356(4) 0.0292(13) Uani 1 1 d . .
H32A H 0.3865 0.5602 0.3911 0.044 Uiso 1 1 calc R U
H32B H 0.3758 0.5333 0.2936 0.044 Uiso 1 1 calc R U
H32C H 0.2975 0.4583 0.3392 0.044 Uiso 1 1 calc R U
C33 C 0.1615(5) 0.6126(6) 0.2229(3) 0.0313(13) Uani 1 1 d . .
H33A H 0.1212 0.5341 0.2266 0.047 Uiso 1 1 calc R U
H33B H 0.2025 0.6028 0.1807 0.047 Uiso 1 1 calc R U
H33C H 0.1073 0.6822 0.2061 0.047 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 0.0000 0.0000 '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
N1 Se1 Cl11 107.17(15)
N2 Se2 N1 97.85(19)
N2 Se3 N3 102.55(18)
N3 Se4 Cl41 105.08(14)
C10 N1 Se1 124.4(3)
C10 N1 Se2 114.8(3)
Se1 N1 Se2 116.7(2)
C20 N2 Se2 122.2(3)
C20 N2 Se3 122.3(3)
Se2 N2 Se3 115.5(2)
C30 N3 Se4 119.3(3)
C30 N3 Se3 120.8(3)
Se4 N3 Se3 111.5(2)
N1 C10 C13 107.3(4)
N1 C10 C11 109.5(4)
C13 C10 C11 111.8(5)
N1 C10 C12 109.6(4)
C13 C10 C12 109.0(5)
C11 C10 C12 109.5(5)
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
C10 C12 H12A 109.5
C10 C12 H12B 109.5
H12A C12 H12B 109.5
C10 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C10 C13 H13A 109.5
C10 C13 H13B 109.5
H13A C13 H13B 109.5
C10 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
N2 C20 C21 107.9(4)
N2 C20 C23 109.5(4)
C21 C20 C23 110.3(4)
N2 C20 C22 110.2(4)
C21 C20 C22 110.7(4)
C23 C20 C22 108.3(5)
C20 C21 H21A 109.5
C20 C21 H21B 109.5
H21A C21 H21B 109.5
C20 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C20 C22 H22A 109.5
C20 C22 H22B 109.5
H22A C22 H22B 109.5
C20 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
C20 C23 H23A 109.5
C20 C23 H23B 109.5
H23A C23 H23B 109.5
C20 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
N3 C30 C31 107.9(4)
N3 C30 C32 108.2(4)
C31 C30 C32 108.6(5)
N3 C30 C33 110.1(4)
C31 C30 C33 111.0(5)
C32 C30 C33 111.0(5)
C30 C31 H31A 109.5
C30 C31 H31B 109.5
H31A C31 H31B 109.5
C30 C31 H31C 109.5
H31A C31 H31C 109.5
H31B C31 H31C 109.5
C30 C32 H32A 109.5
C30 C32 H32B 109.5
H32A C32 H32B 109.5
C30 C32 H32C 109.5
H32A C32 H32C 109.5
H32B C32 H32C 109.5
C30 C33 H33A 109.5
C30 C33 H33B 109.5
H33A C33 H33B 109.5
C30 C33 H33C 109.5
H33A C33 H33C 109.5
H33B C33 H33C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Se1 N1 1.754(4)
Se1 Cl11 2.2761(16)
Se2 N2 1.806(4)
Se2 N1 1.933(4)
Se3 N2 1.839(4)
Se3 N3 1.907(4)
Se4 N3 1.791(4)
Se4 Cl41 2.2536(17)
N1 C10 1.518(6)
N2 C20 1.511(6)
N3 C30 1.517(6)
C10 C13 1.518(9)
C10 C11 1.531(8)
C10 C12 1.528(8)
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C20 C21 1.514(7)
C20 C23 1.527(7)
C20 C22 1.522(7)
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
C22 H22A 0.9800
C22 H22B 0.9800
C22 H22C 0.9800
C23 H23A 0.9800
C23 H23B 0.9800
C23 H23C 0.9800
C30 C31 1.522(7)
C30 C32 1.518(7)
C30 C33 1.532(8)
C31 H31A 0.9800
C31 H31B 0.9800
C31 H31C 0.9800
C32 H32A 0.9800
C32 H32B 0.9800
C32 H32C 0.9800
C33 H33A 0.9800
C33 H33B 0.9800
C33 H33C 0.9800
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
Cl11 Se1 N1 C10 -78.4(4)
Cl11 Se1 N1 Se2 77.3(2)
N1 Se2 N2 C20 95.5(4)
N1 Se2 N2 Se3 -84.1(3)
N3 Se3 N2 C20 67.6(4)
N3 Se3 N2 Se2 -112.8(2)
Cl41 Se4 N3 C30 91.1(3)
Cl41 Se4 N3 Se3 -57.4(2)
Se1 N1 C10 C13 -133.2(4)
Se2 N1 C10 C13 70.7(5)
Se1 N1 C10 C11 105.2(5)
Se2 N1 C10 C11 -50.9(6)
Se1 N1 C10 C12 -15.0(6)
Se2 N1 C10 C12 -171.1(4)
Se2 N2 C20 C21 86.5(5)
Se3 N2 C20 C21 -94.0(5)
Se2 N2 C20 C23 -153.5(4)
Se3 N2 C20 C23 26.1(6)
Se2 N2 C20 C22 -34.5(6)
Se3 N2 C20 C22 145.1(4)
Se4 N3 C30 C31 52.9(5)
Se3 N3 C30 C31 -161.6(4)
Se4 N3 C30 C32 170.3(3)
Se3 N3 C30 C32 -44.3(5)
Se4 N3 C30 C33 -68.3(5)
Se3 N3 C30 C33 77.2(5)
