#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:01:21 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178709 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/20/4082068.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_4082068
loop_
_publ_author_name
'Rakesh, Prakul'
'Singh, Harkesh B.'
'Butcher, Ray J.'
_publ_section_title
;
 Synthesis of Selenenium Ions: Isolation of Highly Conjugated,
 pH-Sensitive
 4,4′-Bis(methylimino)-1,1′-binaphthylene-5-diselenenium(II)
 Triflate
;
_journal_issue                   24
_journal_name_full               Organometallics
_journal_page_first              7275
_journal_paper_doi               10.1021/om400460z
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C22 H16 N2 Se2, 2(C F3 O3 S)'
_chemical_formula_sum            'C24 H16 F6 N2 O6 S2 Se2'
_chemical_formula_weight         764.43
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.6378(19)
_cell_length_b                   15.2112(8)
_cell_length_c                   7.9432(5)
_cell_measurement_reflns_used    5558
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      32.7059
_cell_measurement_theta_min      5.1173
_cell_volume                     2614.4(3)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_molecular_graphics    'SHELXLTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXLTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1168
_diffrn_reflns_av_sigmaI/netI    0.1292
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17731
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.86
_diffrn_reflns_theta_min         5.13
_exptl_absorpt_coefficient_mu    3.077
_exptl_absorpt_correction_T_max  0.899
_exptl_absorpt_correction_T_min  0.409
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.942
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'needle plate'
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.7154
_exptl_crystal_size_mid          0.1686
_exptl_crystal_size_min          0.0347
_refine_diff_density_max         1.465
_refine_diff_density_min         -0.981
_refine_diff_density_rms         0.154
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4465
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.1350
_refine_ls_R_factor_gt           0.0849
_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)+(0.0504P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1566
_refine_ls_wR_factor_ref         0.1778
_reflns_number_gt                2735
_reflns_number_total             4465
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400460z_si_002.cif
_cod_data_source_block           19
_cod_database_code               4082068
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, 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
Se Se 0.47317(2) 0.54217(3) 0.72528(7) 0.02444(17) Uani 1 1 d .
S S 0.62863(6) 0.56643(9) 0.65317(17) 0.0244(3) Uani 1 1 d .
F1 F 0.68973(19) 0.7120(3) 0.6001(5) 0.0594(12) Uani 1 1 d .
F2 F 0.6379(2) 0.7098(2) 0.8282(5) 0.0540(11) Uani 1 1 d .
F3 F 0.72221(19) 0.6365(3) 0.8113(5) 0.0550(11) Uani 1 1 d .
O1 O 0.57171(16) 0.6065(2) 0.5915(4) 0.0288(8) Uani 1 1 d .
O2 O 0.66691(18) 0.5293(3) 0.5245(5) 0.0364(10) Uani 1 1 d .
O3 O 0.62031(19) 0.5138(3) 0.8019(5) 0.0320(9) Uani 1 1 d .
N1 N 0.3961(2) 0.5052(3) 0.8017(5) 0.0236(9) Uani 1 1 d .
C1 C 0.4372(2) 0.6545(3) 0.7081(6) 0.0221(10) Uani 1 1 d .
C2 C 0.4644(2) 0.7333(3) 0.6565(6) 0.0229(10) Uani 1 1 d .
H2A H 0.5070 0.7366 0.6274 0.027 Uiso 1 1 calc R
C3 C 0.4265(2) 0.8063(3) 0.6498(6) 0.0247(11) Uani 1 1 d .
H3A H 0.4436 0.8606 0.6130 0.030 Uiso 1 1 calc R
C4 C 0.3640(2) 0.8039(3) 0.6948(6) 0.0223(10) Uani 1 1 d .
H4A H 0.3395 0.8554 0.6833 0.027 Uiso 1 1 calc R
C5 C 0.3373(2) 0.7270(3) 0.7562(6) 0.0210(10) Uani 1 1 d .
C6 C 0.2717(2) 0.7152(3) 0.8033(6) 0.0207(10) Uani 1 1 d .
C7 C 0.2532(2) 0.6283(3) 0.8578(6) 0.0226(10) Uani 1 1 d .
H7A H 0.2114 0.6204 0.8913 0.027 Uiso 1 1 calc R
C8 C 0.2913(2) 0.5571(3) 0.8645(6) 0.0229(10) Uani 1 1 d .
H8A H 0.2767 0.5020 0.9044 0.028 Uiso 1 1 calc R
C9 C 0.3536(2) 0.5672(3) 0.8105(6) 0.0220(10) Uani 1 1 d .
C10 C 0.3752(2) 0.6516(3) 0.7600(5) 0.0199(10) Uani 1 1 d .
C11 C 0.3871(3) 0.4107(3) 0.8312(7) 0.0277(11) Uani 1 1 d .
H11A H 0.3432 0.3989 0.8515 0.042 Uiso 1 1 calc R
H11B H 0.4113 0.3924 0.9296 0.042 Uiso 1 1 calc R
H11C H 0.4009 0.3777 0.7321 0.042 Uiso 1 1 calc R
C1A C 0.6730(3) 0.6610(4) 0.7273(7) 0.0368(14) 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 0.0000 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
N1 Se C1 85.8(2) .
O2 S O3 116.1(2) .
O2 S O1 114.4(2) .
O3 S O1 113.7(2) .
O2 S C1A 103.7(3) .
O3 S C1A 103.9(3) .
O1 S C1A 102.8(3) .
C9 N1 C11 126.8(4) .
C9 N1 Se 115.2(4) .
C11 N1 Se 117.8(3) .
C2 C1 C10 121.1(5) .
C2 C1 Se 128.7(4) .
C10 C1 Se 110.2(4) .
C3 C2 C1 116.7(5) .
C3 C2 H2A 121.6 .
C1 C2 H2A 121.6 .
C2 C3 C4 122.9(5) .
C2 C3 H3A 118.5 .
C4 C3 H3A 118.5 .
C5 C4 C3 120.9(5) .
C5 C4 H4A 119.5 .
C3 C4 H4A 119.5 .
C4 C5 C10 116.6(5) .
C4 C5 C6 126.2(5) .
C10 C5 C6 117.0(4) .
C6 C6 C7 119.9(5) 2_565
C6 C6 C5 123.1(5) 2_565
C7 C6 C5 116.9(4) .
C8 C7 C6 124.8(5) .
C8 C7 H7A 117.6 .
C6 C7 H7A 117.6 .
C7 C8 C9 118.4(5) .
C7 C8 H8A 120.8 .
C9 C8 H8A 120.8 .
N1 C9 C8 126.8(5) .
N1 C9 C10 113.6(5) .
C8 C9 C10 119.6(5) .
C1 C10 C5 121.6(5) .
C1 C10 C9 115.2(5) .
C5 C10 C9 123.2(5) .
N1 C11 H11A 109.5 .
N1 C11 H11B 109.5 .
H11A C11 H11B 109.5 .
N1 C11 H11C 109.5 .
H11A C11 H11C 109.5 .
H11B C11 H11C 109.5 .
F3 C1A F1 109.4(5) .
F3 C1A F2 108.4(5) .
F1 C1A F2 106.8(5) .
F3 C1A S 111.5(4) .
F1 C1A S 111.1(4) .
F2 C1A S 109.6(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Se N1 1.862(4) .
Se C1 1.883(5) .
S O2 1.432(4) .
S O3 1.439(4) .
S O1 1.459(4) .
S C1A 1.826(6) .
F1 C1A 1.324(7) .
F2 C1A 1.330(8) .
F3 C1A 1.311(7) .
N1 C9 1.320(7) .
N1 C11 1.470(6) .
C1 C2 1.397(7) .
C1 C10 1.404(7) .
C2 C3 1.383(7) .
C2 H2A 0.9500 .
C3 C4 1.398(7) .
C3 H3A 0.9500 .
C4 C5 1.394(7) .
C4 H4A 0.9500 .
C5 C10 1.411(7) .
C5 C6 1.477(7) .
C6 C6 1.416(10) 2_565
C6 C7 1.447(7) .
C7 C8 1.363(7) .
C7 H7A 0.9500 .
C8 C9 1.422(7) .
C8 H8A 0.9500 .
C9 C10 1.424(7) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2A O1 0.95 2.44 3.061(6) 122.8 .
C4 H4A O3 0.95 2.56 3.210(6) 125.5 3_656
C7 H7A O2 0.95 2.56 3.180(6) 123.0 4_466
C8 H8A O2 0.95 2.49 3.123(6) 124.3 4_466
C11 H11B O3 0.98 2.66 3.137(6) 110.6 5_667
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
C1 Se N1 C9 -0.1(4) . .
C1 Se N1 C11 174.6(4) . .
N1 Se C1 C2 179.1(5) . .
N1 Se C1 C10 0.4(3) . .
C10 C1 C2 C3 -3.7(7) . .
Se C1 C2 C3 177.7(4) . .
C1 C2 C3 C4 1.2(7) . .
C2 C3 C4 C5 2.7(7) . .
C3 C4 C5 C10 -3.9(7) . .
C3 C4 C5 C6 -178.1(4) . .
C4 C5 C6 C6 -5.1(6) . 2_565
C10 C5 C6 C6 -179.3(3) . 2_565
C4 C5 C6 C7 177.4(5) . .
C10 C5 C6 C7 3.2(6) . .
C6 C6 C7 C8 -179.2(4) 2_565 .
C5 C6 C7 C8 -1.7(7) . .
C6 C7 C8 C9 -1.7(7) . .
C11 N1 C9 C8 6.0(8) . .
Se N1 C9 C8 -179.9(4) . .
C11 N1 C9 C10 -174.5(4) . .
Se N1 C9 C10 -0.4(5) . .
C7 C8 C9 N1 -177.1(5) . .
C7 C8 C9 C10 3.4(7) . .
C2 C1 C10 C5 2.5(7) . .
Se C1 C10 C5 -178.7(4) . .
C2 C1 C10 C9 -179.6(4) . .
Se C1 C10 C9 -0.8(5) . .
C4 C5 C10 C1 1.4(7) . .
C6 C5 C10 C1 176.2(4) . .
C4 C5 C10 C9 -176.4(4) . .
C6 C5 C10 C9 -1.6(7) . .
N1 C9 C10 C1 0.7(6) . .
C8 C9 C10 C1 -179.7(4) . .
N1 C9 C10 C5 178.7(4) . .
C8 C9 C10 C5 -1.8(7) . .
O2 S C1A F3 -70.2(5) . .
O3 S C1A F3 51.5(5) . .
O1 S C1A F3 170.3(4) . .
O2 S C1A F1 52.1(5) . .
O3 S C1A F1 173.8(5) . .
O1 S C1A F1 -67.4(5) . .
O2 S C1A F2 169.8(4) . .
O3 S C1A F2 -68.5(4) . .
O1 S C1A F2 50.3(4) . .
