#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:14:46 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179052 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/14/4301467.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_4301467
loop_
_publ_author_name
'Jason L. Dutton'
'Paul J. Ragogna'
_publ_contact_author_address
;1151 Richmond Street 
London Ontario
N6A 5B7
;
_publ_contact_author_email       pragogna@uwo.ca
_publ_contact_author_name        'Paul J. Ragogna'
_publ_section_title
;
Donor-Acceptor Chemistry at Heavy Chalcogen Centers
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1722
_journal_page_last               1730
_journal_paper_doi               10.1021/ic801883e
_journal_volume                  48
_journal_year                    2009
_chemical_formula_moiety         'C13 H21 N4 Se, C F3 O3 S'
_chemical_formula_sum            'C14 H21 F3 N4 O3 S Se'
_chemical_formula_weight         461.37
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.31(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8047(16)
_cell_length_b                   7.4665(15)
_cell_length_c                   33.101(7)
_cell_measurement_reflns_used    38867
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1920.6(7)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2001)'
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full .957
_diffrn_measured_fraction_theta_max .957
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'φ scans, and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_sigmaI/netI    0.0678
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            9546
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         2.64
_exptl_absorpt_coefficient_mu    2.113
_exptl_absorpt_correction_T_max  0.9017
_exptl_absorpt_correction_T_min  0.6773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO-SMN (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         .492
_refine_diff_density_min         -.841
_refine_diff_density_rms         .096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4236
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0501P)²+2.0526P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1312
_reflns_number_gt                2808
_reflns_number_total             4236
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic801883e_si_001_4.cif
_cod_data_source_block           4DMAP
_cod_original_cell_volume        1920.7(7)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4301467
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.80554(6) 0.66390(5) 0.097278(12) 0.03742(16) Uani 1 1 d . . .
S1 S 0.35975(15) 0.06662(19) 0.14765(4) 0.0502(3) Uani 1 1 d . . .
N1 N 0.6115(5) 0.6047(5) 0.06647(11) 0.0391(8) Uani 1 1 d . . .
N2 N 0.6760(5) 0.6037(4) 0.14409(11) 0.0394(9) Uani 1 1 d . . .
N4 N 1.2052(4) 0.8360(4) -0.05691(11) 0.0378(8) Uani 1 1 d . . .
N3 N 0.9192(4) 0.7157(4) 0.03986(10) 0.0339(8) Uani 1 1 d . . .
C31 C 1.0838(5) 0.7686(6) 0.04548(13) 0.0380(10) Uani 1 1 d . . .
H31A H 1.1342 0.7800 0.0726 0.046 Uiso 1 1 calc R . .
C34 C 0.9394(5) 0.7411(5) -0.03157(12) 0.0339(9) Uani 1 1 d . . .
H34A H 0.8839 0.7315 -0.0583 0.041 Uiso 1 1 calc R . .
C2 C 0.5229(7) 0.5541(6) 0.13127(14) 0.0486(12) Uani 1 1 d . . .
H2A H 0.4393 0.5192 0.1489 0.058 Uiso 1 1 calc R . .
C35 C 0.8512(5) 0.7020(5) 0.00103(12) 0.0346(9) Uani 1 1 d . . .
H35A H 0.7353 0.6628 -0.0039 0.041 Uiso 1 1 calc R . .
C33 C 1.1127(5) 0.7959(5) -0.02568(13) 0.0323(9) Uani 1 1 d . . .
C32 C 1.1832(5) 0.8071(5) 0.01523(13) 0.0388(10) Uani 1 1 d . . .
H32A H 1.2999 0.8414 0.0214 0.047 Uiso 1 1 calc R . .
C21 C 0.2668(7) 0.1019(8) 0.19487(15) 0.0566(13) Uani 1 1 d . . .
C1 C 0.4904(6) 0.5562(6) 0.08825(14) 0.0463(11) Uani 1 1 d . . .
H1B H 0.3808 0.5224 0.0757 0.056 Uiso 1 1 calc R . .
F3 F 0.0976(4) 0.1070(4) 0.18984(10) 0.0734(9) Uani 1 1 d . . .
C37 C 1.1258(6) 0.8392(5) -0.09847(13) 0.0396(10) Uani 1 1 d . . .
H37A H 1.0794 0.7204 -0.1058 0.059 Uiso 1 1 calc R . .
H37B H 1.2121 0.8721 -0.1168 0.059 Uiso 1 1 calc R . .
H37C H 1.0323 0.9273 -0.1008 0.059 Uiso 1 1 calc R . .
O3 O 0.2981(4) 0.2170(5) 0.12374(11) 0.0638(10) Uani 1 1 d . . .
O2 O 0.2888(5) -0.1023(5) 0.13396(11) 0.0729(11) Uani 1 1 d . . .
F2 F 0.3110(5) -0.0268(6) 0.22133(10) 0.1028(13) Uani 1 1 d . . .
C36 C 1.3835(5) 0.8921(6) -0.04988(15) 0.0473(12) Uani 1 1 d . . .
H36A H 1.3898 1.0056 -0.0349 0.071 Uiso 1 1 calc R . .
H36B H 1.4315 0.9083 -0.0760 0.071 Uiso 1 1 calc R . .
H36C H 1.4495 0.8005 -0.0340 0.071 Uiso 1 1 calc R . .
O1 O 0.5401(4) 0.0685(7) 0.15947(12) 0.0947(15) Uani 1 1 d . . .
C11 C 0.7519(7) 0.6071(6) 0.18719(14) 0.0504(13) Uani 1 1 d . . .
F1 F 0.3179(5) 0.2577(6) 0.21156(12) 0.1132(14) Uani 1 1 d . . .
C14 C 0.8585(9) 0.4378(7) 0.19344(16) 0.082(2) Uani 1 1 d . . .
H14A H 0.7842 0.3330 0.1882 0.124 Uiso 1 1 calc R . .
H14B H 0.9114 0.4337 0.2214 0.124 Uiso 1 1 calc R . .
H14C H 0.9487 0.4375 0.1747 0.124 Uiso 1 1 calc R . .
C13 C 0.8631(7) 0.7725(7) 0.19245(15) 0.0620(15) Uani 1 1 d . . .
H13A H 0.9505 0.7695 0.1730 0.093 Uiso 1 1 calc R . .
H13B H 0.9198 0.7758 0.2201 0.093 Uiso 1 1 calc R . .
H13C H 0.7913 0.8794 0.1876 0.093 Uiso 1 1 calc R . .
C12 C 0.6098(9) 0.6129(8) 0.21581(18) 0.083(2) Uani 1 1 d . . .
H12A H 0.5365 0.7176 0.2095 0.124 Uiso 1 1 calc R . .
H12B H 0.6613 0.6211 0.2439 0.124 Uiso 1 1 calc R . .
H12C H 0.5403 0.5037 0.2125 0.124 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F .0171 .0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -.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
N1 Se1 N2 85.63(16) . . ?
N1 Se1 N3 86.52(14) . . ?
N2 Se1 N3 172.07(14) . . ?
O1 S1 O3 114.6(3) . . ?
O1 S1 O2 116.0(3) . . ?
O3 S1 O2 114.5(2) . . ?
O1 S1 C21 103.1(2) . . ?
O3 S1 C21 102.9(3) . . ?
O2 S1 C21 103.2(2) . . ?
C1 N1 Se1 111.9(3) . . ?
C2 N2 C11 126.5(4) . . ?
C2 N2 Se1 109.5(3) . . ?
C11 N2 Se1 123.9(3) . . ?
C33 N4 C36 121.0(4) . . ?
C33 N4 C37 121.1(3) . . ?
C36 N4 C37 117.7(4) . . ?
C31 N3 C35 116.3(4) . . ?
C31 N3 Se1 112.9(3) . . ?
C35 N3 Se1 130.8(3) . . ?
N3 C31 C32 124.6(4) . . ?
N3 C31 H31A 117.7 . . ?
C32 C31 H31A 117.7 . . ?
C35 C34 C33 120.1(4) . . ?
C35 C34 H34A 120.0 . . ?
C33 C34 H34A 120.0 . . ?
N2 C2 C1 113.7(4) . . ?
N2 C2 H2A 123.2 . . ?
C1 C2 H2A 123.2 . . ?
N3 C35 C34 123.7(4) . . ?
N3 C35 H35A 118.2 . . ?
C34 C35 H35A 118.2 . . ?
N4 C33 C34 122.3(4) . . ?
N4 C33 C32 122.1(4) . . ?
C34 C33 C32 115.6(4) . . ?
C31 C32 C33 119.8(4) . . ?
C31 C32 H32A 120.1 . . ?
C33 C32 H32A 120.1 . . ?
F3 C21 F2 107.6(4) . . ?
F3 C21 F1 106.6(5) . . ?
F2 C21 F1 108.0(4) . . ?
F3 C21 S1 112.0(3) . . ?
F2 C21 S1 111.5(4) . . ?
F1 C21 S1 111.0(4) . . ?
N1 C1 C2 119.3(4) . . ?
N1 C1 H1B 120.3 . . ?
C2 C1 H1B 120.3 . . ?
N4 C37 H37A 109.5 . . ?
N4 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
N4 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N4 C36 H36A 109.5 . . ?
N4 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N4 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N2 C11 C13 107.3(4) . . ?
N2 C11 C14 106.3(4) . . ?
C13 C11 C14 111.3(5) . . ?
N2 C11 C12 110.3(4) . . ?
C13 C11 C12 110.4(4) . . ?
C14 C11 C12 111.1(5) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
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
Se1 N1 1.801(4) . ?
Se1 N2 1.979(4) . ?
Se1 N3 2.205(3) . ?
S1 O1 1.425(4) . ?
S1 O3 1.431(4) . ?
S1 O2 1.434(4) . ?
S1 C21 1.802(5) . ?
N1 C1 1.292(5) . ?
N2 C2 1.285(6) . ?
N2 C11 1.494(6) . ?
N4 C33 1.348(5) . ?
N4 C36 1.451(5) . ?
N4 C37 1.456(5) . ?
N3 C31 1.341(5) . ?
N3 C35 1.348(5) . ?
C31 C32 1.353(6) . ?
C31 H31A 0.9500 . ?
C34 C35 1.364(6) . ?
C34 C33 1.410(6) . ?
C34 H34A 0.9500 . ?
C2 C1 1.423(6) . ?
C2 H2A 0.9500 . ?
C35 H35A 0.9500 . ?
C33 C32 1.416(6) . ?
C32 H32A 0.9500 . ?
C21 F3 1.316(5) . ?
C21 F2 1.324(6) . ?
C21 F1 1.333(6) . ?
C1 H1B 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C11 C13 1.510(7) . ?
C11 C14 1.516(7) . ?
C11 C12 1.524(7) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Se1 N1 C1 0.4(3) . . . . ?
N3 Se1 N1 C1 179.3(3) . . . . ?
N1 Se1 N2 C2 -0.2(3) . . . . ?
N3 Se1 N2 C2 -8.3(11) . . . . ?
N1 Se1 N2 C11 176.6(3) . . . . ?
N3 Se1 N2 C11 168.6(8) . . . . ?
N1 Se1 N3 C31 -179.4(3) . . . . ?
N2 Se1 N3 C31 -171.3(8) . . . . ?
N1 Se1 N3 C35 0.3(4) . . . . ?
N2 Se1 N3 C35 8.3(11) . . . . ?
C35 N3 C31 C32 -0.4(6) . . . . ?
Se1 N3 C31 C32 179.3(3) . . . . ?
C11 N2 C2 C1 -176.7(4) . . . . ?
Se1 N2 C2 C1 0.0(5) . . . . ?
C31 N3 C35 C34 -1.0(6) . . . . ?
Se1 N3 C35 C34 179.4(3) . . . . ?
C33 C34 C35 N3 1.4(6) . . . . ?
C36 N4 C33 C34 180.0(4) . . . . ?
C37 N4 C33 C34 5.3(6) . . . . ?
C36 N4 C33 C32 0.3(6) . . . . ?
C37 N4 C33 C32 -174.4(4) . . . . ?
C35 C34 C33 N4 180.0(4) . . . . ?
C35 C34 C33 C32 -0.3(5) . . . . ?
N3 C31 C32 C33 1.4(6) . . . . ?
N4 C33 C32 C31 178.7(4) . . . . ?
C34 C33 C32 C31 -0.9(6) . . . . ?
O1 S1 C21 F3 179.0(4) . . . . ?
O3 S1 C21 F3 59.5(4) . . . . ?
O2 S1 C21 F3 -59.9(4) . . . . ?
O1 S1 C21 F2 -60.4(4) . . . . ?
O3 S1 C21 F2 -179.9(4) . . . . ?
O2 S1 C21 F2 60.7(4) . . . . ?
O1 S1 C21 F1 60.1(5) . . . . ?
O3 S1 C21 F1 -59.4(4) . . . . ?
O2 S1 C21 F1 -178.8(4) . . . . ?
Se1 N1 C1 C2 -0.5(5) . . . . ?
N2 C2 C1 N1 0.3(6) . . . . ?
C2 N2 C11 C13 -141.9(5) . . . . ?
Se1 N2 C11 C13 41.8(5) . . . . ?
C2 N2 C11 C14 98.9(6) . . . . ?
Se1 N2 C11 C14 -77.4(5) . . . . ?
C2 N2 C11 C12 -21.6(6) . . . . ?
Se1 N2 C11 C12 162.0(3) . . . . ?
