#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/43/7204337.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_7204337
loop_
_publ_author_name
'Norman A. Bell'
'David J. Crouch'
'Derek J. Simmonds'
'Andres E. Goeta'
'Thomas Gelbrich'
'Michael B. Hursthouse'
_publ_section_title
;
 Structural and solvatochromic studies of a series of
 tricyanoquinodimethane-based zwitterions
;
_journal_issue                   5
_journal_name_full               'J. Mater. Chem.'
_journal_page_first              1274
_journal_page_last               1279
_journal_paper_doi               10.1039/b111392p
_journal_volume                  12
_journal_year                    2002
_chemical_formula_sum            'C23 H18 N4 Se'
_chemical_formula_weight         429.37
_chemical_name_systematic
;
(Z)-β-(N-butyl-2-benzoselenozolium)
-α-cyano-4-styryldicyanomethanide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                83.317(2)
_cell_angle_beta                 81.4890(10)
_cell_angle_gamma                89.601(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0663(3)
_cell_length_b                   9.4561(2)
_cell_length_c                   12.8115(5)
_cell_measurement_reflns_used    12468
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.2
_cell_volume                     959.83(6)
_computing_cell_refinement       'DENZO (Otwinowski, 1997)'
_computing_data_collection       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO (Otwinowski, 1997)'
_computing_molecular_graphics    ?'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'DIRDIF-96 (Beurskens et al., 1996)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD Diffractometer'
_diffrn_measurement_method       'ω and π 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  0.0662
_diffrn_reflns_av_sigmaI/netI    0.0793
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12251
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.17
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.972
_exptl_absorpt_correction_T_max  0.827
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995 & 1997)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.0038(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         3746
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0401
_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)+(0.0278P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0784
_reflns_number_gt                2937
_reflns_number_total             3746
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b111392p.txt
_cod_data_source_block           s92
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7204337
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.14486(4) 0.18128(3) 0.03079(2) 0.02473(13) Uani 1 d . . .
N1 N 0.2602(3) 0.2933(2) 0.18882(16) 0.0198(5) Uani 1 d . . .
N2 N 0.0833(3) 0.3742(2) -0.17871(19) 0.0322(6) Uani 1 d . . .
N3 N 0.5094(3) 1.2810(2) -0.16521(18) 0.0308(6) Uani 1 d . . .
N4 N 0.3054(5) 1.1879(3) -0.4444(2) 0.0700(12) Uani 1 d . . .
C1 C 0.1532(4) 0.0732(3) 0.1611(2) 0.0230(7) Uani 1 d . . .
C2 C 0.2170(3) 0.1520(3) 0.2314(2) 0.0203(6) Uani 1 d . . .
C3 C 0.2316(4) 0.0914(3) 0.3339(2) 0.0271(7) Uani 1 d . . .
H3 H 0.278(3) 0.143(3) 0.3844(19) 0.019(7) Uiso 1 d . . .
C4 C 0.1794(4) -0.0473(3) 0.3636(2) 0.0341(8) Uani 1 d . . .
H4 H 0.185(4) -0.094(3) 0.432(2) 0.040(9) Uiso 1 d . . .
C5 C 0.1158(4) -0.1268(3) 0.2931(2) 0.0324(8) Uani 1 d . . .
H5 H 0.073(4) -0.222(3) 0.314(2) 0.040(9) Uiso 1 d . . .
C6 C 0.1034(4) -0.0688(3) 0.1918(2) 0.0278(7) Uani 1 d . . .
H6 H 0.064(4) -0.121(3) 0.141(2) 0.028(8) Uiso 1 d . . .
C7 C 0.3437(4) 0.3838(3) 0.2541(2) 0.0217(6) Uani 1 d . . .
H7A H 0.412(3) 0.457(2) 0.2057(18) 0.007(6) Uiso 1 d . . .
H7B H 0.412(4) 0.321(3) 0.287(2) 0.022(8) Uiso 1 d . . .
C8 C 0.2246(4) 0.4467(3) 0.3393(2) 0.0242(7) Uani 1 d . . .
H8A H 0.156(3) 0.371(3) 0.3851(19) 0.020(7) Uiso 1 d . . .
H8B H 0.155(4) 0.514(3) 0.305(2) 0.021(7) Uiso 1 d . . .
C9 C 0.3239(4) 0.5200(3) 0.4110(2) 0.0295(7) Uani 1 d . . .
H9A H 0.386(3) 0.594(3) 0.369(2) 0.025(7) Uiso 1 d . . .
H9B H 0.408(4) 0.448(3) 0.436(2) 0.030(8) Uiso 1 d . . .
C10 C 0.2160(5) 0.5706(4) 0.5064(3) 0.0351(8) Uani 1 d . . .
H10A H 0.287(4) 0.626(3) 0.545(2) 0.041(9) Uiso 1 d . . .
H10B H 0.162(4) 0.483(4) 0.556(3) 0.058(10) Uiso 1 d . . .
H10C H 0.128(4) 0.628(3) 0.487(2) 0.042(10) Uiso 1 d . . .
C11 C 0.2300(3) 0.3345(3) 0.0890(2) 0.0192(6) Uani 1 d . . .
C12 C 0.2622(4) 0.4736(3) 0.0366(2) 0.0218(6) Uani 1 d . . .
H12 H 0.306(3) 0.536(3) 0.079(2) 0.021(7) Uiso 1 d . . .
C13 C 0.2296(3) 0.5277(3) -0.0634(2) 0.0192(6) Uani 1 d . . .
C14 C 0.1506(4) 0.4395(3) -0.1269(2) 0.0218(6) Uani 1 d . . .
C15 C 0.2648(3) 0.6716(3) -0.1129(2) 0.0209(6) Uani 1 d . . .
C16 C 0.2231(4) 0.7191(3) -0.2141(2) 0.0255(7) Uani 1 d . . .
H16 H 0.1705 0.6543 -0.2506 0.021(7) Uiso 1 calc R . .
C17 C 0.2555(4) 0.8546(3) -0.2615(2) 0.0262(7) Uani 1 d . . .
H17 H 0.221(4) 0.887(3) -0.330(2) 0.035(8) Uiso 1 d . . .
C18 C 0.3340(4) 0.9559(3) -0.2105(2) 0.0220(6) Uani 1 d . . .
C19 C 0.3770(4) 0.9072(3) -0.1096(2) 0.0225(7) Uani 1 d . . .
H19 H 0.427(4) 0.971(3) -0.073(2) 0.028(8) Uiso 1 d . . .
C20 C 0.3438(4) 0.7720(3) -0.0618(2) 0.0234(7) Uani 1 d . . .
H20 H 0.372(4) 0.742(3) 0.006(2) 0.029(8) Uiso 1 d . . .
C21 C 0.3702(4) 1.0974(3) -0.2581(2) 0.0267(7) Uani 1 d . . .
C22 C 0.4485(4) 1.1975(3) -0.2066(2) 0.0251(7) Uani 1 d . . .
C23 C 0.3333(5) 1.1475(3) -0.3609(3) 0.0395(9) Uani 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'
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
C1 Se1 C11 87.10(11) . . ?
C11 N1 C2 116.9(2) . . ?
C11 N1 C7 124.7(2) . . ?
C2 N1 C7 118.3(2) . . ?
C2 C1 C6 120.7(3) . . ?
C2 C1 Se1 111.44(18) . . ?
C6 C1 Se1 127.9(2) . . ?
C1 C2 C3 120.6(2) . . ?
C1 C2 N1 113.8(2) . . ?
C3 C2 N1 125.6(2) . . ?
C4 C3 C2 118.1(3) . . ?
C4 C3 H3 119.2(15) . . ?
C2 C3 H3 122.7(15) . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 H4 122.2(18) . . ?
C5 C4 H4 116.4(18) . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 117.2(18) . . ?
C4 C5 H5 121.9(18) . . ?
C5 C6 C1 118.4(3) . . ?
C5 C6 H6 123.3(17) . . ?
C1 C6 H6 118.3(17) . . ?
N1 C7 C8 114.2(2) . . ?
N1 C7 H7A 108.4(13) . . ?
C8 C7 H7A 112.6(13) . . ?
N1 C7 H7B 103.0(16) . . ?
C8 C7 H7B 108.3(16) . . ?
H7A C7 H7B 110(2) . . ?
C7 C8 C9 110.0(3) . . ?
C7 C8 H8A 110.3(14) . . ?
C9 C8 H8A 107.2(15) . . ?
C7 C8 H8B 108.4(15) . . ?
C9 C8 H8B 110.3(15) . . ?
H8A C8 H8B 111(2) . . ?
C10 C9 C8 113.7(3) . . ?
C10 C9 H9A 111.8(15) . . ?
C8 C9 H9A 107.9(16) . . ?
C10 C9 H9B 109.7(15) . . ?
C8 C9 H9B 106.5(15) . . ?
H9A C9 H9B 107(2) . . ?
C9 C10 H10A 109.4(17) . . ?
C9 C10 H10B 109.4(17) . . ?
H10A C10 H10B 110(3) . . ?
C9 C10 H10C 112.4(19) . . ?
H10A C10 H10C 109(3) . . ?
H10B C10 H10C 106(3) . . ?
N1 C11 C12 123.7(2) . . ?
N1 C11 Se1 110.64(17) . . ?
C12 C11 Se1 125.7(2) . . ?
C13 C12 C11 128.0(2) . . ?
C13 C12 H12 118.3(16) . . ?
C11 C12 H12 113.6(16) . . ?
C12 C13 C14 120.4(2) . . ?
C12 C13 C15 125.5(2) . . ?
C14 C13 C15 114.1(2) . . ?
N2 C14 C13 177.0(3) . . ?
C16 C15 C20 116.8(2) . . ?
C16 C15 C13 121.8(2) . . ?
C20 C15 C13 121.4(3) . . ?
C17 C16 C15 122.4(2) . . ?
C17 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
C16 C17 C18 121.1(3) . . ?
C16 C17 H17 121.3(16) . . ?
C18 C17 H17 117.5(16) . . ?
C19 C18 C21 121.3(2) . . ?
C19 C18 C17 116.2(2) . . ?
C21 C18 C17 122.4(3) . . ?
C20 C19 C18 122.8(2) . . ?
C20 C19 H19 118.4(17) . . ?
C18 C19 H19 118.8(17) . . ?
C19 C20 C15 120.8(3) . . ?
C19 C20 H20 121.3(16) . . ?
C15 C20 H20 117.9(16) . . ?
C22 C21 C18 122.0(3) . . ?
C22 C21 C23 115.6(2) . . ?
C18 C21 C23 122.4(2) . . ?
N3 C22 C21 178.5(3) . . ?
N4 C23 C21 179.2(4) . . ?
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 C1 1.863(3) . ?
Se1 C11 1.883(2) . ?
N1 C11 1.349(3) . ?
N1 C2 1.409(3) . ?
N1 C7 1.492(3) . ?
N2 C14 1.150(3) . ?
N3 C22 1.151(3) . ?
N4 C23 1.147(4) . ?
C1 C2 1.389(4) . ?
C1 C6 1.399(4) . ?
C2 C3 1.393(4) . ?
C3 C4 1.374(4) . ?
C3 H3 0.97(2) . ?
C4 C5 1.395(4) . ?
C4 H4 0.94(3) . ?
C5 C6 1.366(4) . ?
C5 H5 0.96(3) . ?
C6 H6 0.95(3) . ?
C7 C8 1.518(4) . ?
C7 H7A 0.99(2) . ?
C7 H7B 0.91(3) . ?
C8 C9 1.529(4) . ?
C8 H8A 0.99(2) . ?
C8 H8B 0.95(3) . ?
C9 C10 1.514(4) . ?
C9 H9A 0.93(3) . ?
C9 H9B 1.02(3) . ?
C10 H10A 1.00(3) . ?
C10 H10B 1.04(3) . ?
C10 H10C 0.94(4) . ?
C11 C12 1.412(4) . ?
C12 C13 1.385(4) . ?
C12 H12 0.95(3) . ?
C13 C14 1.443(4) . ?
C13 C15 1.444(3) . ?
C15 C16 1.410(4) . ?
C15 C20 1.419(4) . ?
C16 C17 1.363(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.422(4) . ?
C17 H17 0.97(3) . ?
C18 C19 1.413(4) . ?
C18 C21 1.417(4) . ?
C19 C20 1.362(4) . ?
C19 H19 0.93(3) . ?
C20 H20 0.95(3) . ?
C21 C22 1.416(4) . ?
C21 C23 1.421(4) . ?
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
C11 Se1 C1 C2 -1.3(2) . . . . ?
C11 Se1 C1 C6 178.3(3) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
Se1 C1 C2 C3 179.2(2) . . . . ?
C6 C1 C2 N1 -179.6(3) . . . . ?
Se1 C1 C2 N1 0.0(3) . . . . ?
C11 N1 C2 C1 2.0(4) . . . . ?
C7 N1 C2 C1 -174.8(2) . . . . ?
C11 N1 C2 C3 -177.1(3) . . . . ?
C7 N1 C2 C3 6.1(4) . . . . ?
C1 C2 C3 C4 -0.8(5) . . . . ?
N1 C2 C3 C4 178.3(3) . . . . ?
C2 C3 C4 C5 1.0(5) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C4 C5 C6 C1 -1.1(5) . . . . ?
C2 C1 C6 C5 1.3(5) . . . . ?
Se1 C1 C6 C5 -178.1(2) . . . . ?
C11 N1 C7 C8 103.3(3) . . . . ?
C2 N1 C7 C8 -80.2(3) . . . . ?
N1 C7 C8 C9 172.2(2) . . . . ?
C7 C8 C9 C10 -173.1(3) . . . . ?
C2 N1 C11 C12 178.2(2) . . . . ?
C7 N1 C11 C12 -5.2(4) . . . . ?
C2 N1 C11 Se1 -2.9(3) . . . . ?
C7 N1 C11 Se1 173.6(2) . . . . ?
C1 Se1 C11 N1 2.3(2) . . . . ?
C1 Se1 C11 C12 -178.9(3) . . . . ?
N1 C11 C12 C13 -177.2(3) . . . . ?
Se1 C11 C12 C13 4.2(4) . . . . ?
C11 C12 C13 C14 1.2(5) . . . . ?
C11 C12 C13 C15 179.7(3) . . . . ?
C12 C13 C14 N2 137(5) . . . . ?
C15 C13 C14 N2 -41(5) . . . . ?
C12 C13 C15 C16 -178.1(3) . . . . ?
C14 C13 C15 C16 0.4(4) . . . . ?
C12 C13 C15 C20 2.0(4) . . . . ?
C14 C13 C15 C20 -179.4(3) . . . . ?
C20 C15 C16 C17 -0.2(4) . . . . ?
C13 C15 C16 C17 179.9(3) . . . . ?
C15 C16 C17 C18 0.0(5) . . . . ?
C16 C17 C18 C19 0.6(4) . . . . ?
C16 C17 C18 C21 179.6(3) . . . . ?
C21 C18 C19 C20 180.0(3) . . . . ?
C17 C18 C19 C20 -1.1(4) . . . . ?
C18 C19 C20 C15 0.8(4) . . . . ?
C16 C15 C20 C19 -0.2(4) . . . . ?
C13 C15 C20 C19 179.7(3) . . . . ?
C19 C18 C21 C22 -1.0(4) . . . . ?
C17 C18 C21 C22 -180.0(3) . . . . ?
C19 C18 C21 C23 177.8(3) . . . . ?
C17 C18 C21 C23 -1.1(5) . . . . ?
C18 C21 C22 N3 -129(10) . . . . ?
C23 C21 C22 N3 53(10) . . . . ?
C22 C21 C23 N4 76(21) . . . . ?
C18 C21 C23 N4 -103(21) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21190205
