data_global
_journal_name_full               J.Mater.Chem.

_journal_coden_Cambridge         1145

_publ_contact_author_name        'Zhou Yang'
_publ_contact_author_address     
;
Nonlinear Optics Laboratory
Swiss Federal Institute of Technology
ETH Zurich
Zurich
CH-8093
SWITZERLAND
;

_publ_contact_author_email       ZHOUYANG@PHYS.ETHZ.CH

_publ_section_title              
;
Synthesis and crystal structure of a new stilbazolium
salt with large second-order optical nonlinearity
;
loop_
_publ_author_name
'Zhou Yang'
'Volker Gramlich'
'Peter Gunter'
'Mojca Jazbinsek'
'Blanca Ruiz'

data_salt
_database_code_depnum_ccdc_archive 'CCDC 292764'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H26 N2 O3 S'
_chemical_formula_weight         446.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   7.864(4)
_cell_length_b                   8.054(4)
_cell_length_c                   9.893(5)
_cell_angle_alpha                70.04(5)
_cell_angle_beta                 73.31(5)
_cell_angle_gamma                83.69(5)
_cell_volume                     564.1(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    12
_cell_measurement_theta_min      10
_cell_measurement_theta_max      11

_exptl_crystal_description       platelet
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             236
_exptl_absorpt_coefficient_mu    1.521
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   SHELXPREP

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CAD4
_diffrn_measurement_method       ' \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         1
_diffrn_standards_interval_count 120
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4377
_diffrn_reflns_av_R_equivalents  0.1871
_diffrn_reflns_av_sigmaI/netI    0.1269
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         9.55
_diffrn_reflns_theta_max         72.33
_reflns_number_total             3313
_reflns_number_gt                1392
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CAD4
_computing_cell_refinement       CAD4
_computing_data_reduction        CAD4
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXLTL-Plus
_computing_publication_material  SHELXL-93

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1300P)^2^+7.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.41(8)
_refine_ls_number_reflns         3313
_refine_ls_number_parameters     256
_refine_ls_number_restraints     455
_refine_ls_R_factor_all          0.2150
_refine_ls_R_factor_gt           0.1299
_refine_ls_wR_factor_ref         0.3389
_refine_ls_wR_factor_gt          0.2828
_refine_ls_goodness_of_fit_ref   0.622
_refine_ls_restrained_S_all      0.609
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
S S 0.8407(3) 0.8753(3) 0.1122(2) 0.1021(8) Uani 1 1 d DU . .
O2 O 0.7813(8) 0.9270(9) -0.0276(6) 0.124(2) Uani 1 1 d DU . .
O1 O 0.7019(11) 0.8090(15) 0.2469(9) 0.194(4) Uani 1 1 d DU . .
N1 N 0.3584(5) 0.7116(5) 0.5635(4) 0.0887(19) Uani 1 1 d GDU . .
C2 C 0.3139(6) 0.7590(7) 0.4289(4) 0.095(2) Uani 1 1 d GDU . .
H2A H 0.3928 0.7358 0.3471 0.114 Uiso 1 1 calc R . .
C3 C 0.1515(7) 0.8411(7) 0.4166(5) 0.092(2) Uani 1 1 d GDU . .
H3A H 0.1218 0.8729 0.3265 0.110 Uiso 1 1 calc R . .
C4 C 0.0336(5) 0.8759(6) 0.5389(7) 0.092(2) Uani 1 1 d GDU . .
C5 C 0.0780(5) 0.8284(7) 0.6735(6) 0.098(2) Uani 1 1 d GDU . .
H5A H -0.0009 0.8517 0.7553 0.117 Uiso 1 1 calc R . .
C6 C 0.2404(6) 0.7463(7) 0.6858(4) 0.093(2) Uani 1 1 d GDU . .
H6A H 0.2701 0.7146 0.7759 0.111 Uiso 1 1 calc R . .
C7 C 0.5295(11) 0.6189(13) 0.5718(11) 0.107(3) Uani 1 1 d DU . .
H7A H 0.5903 0.6063 0.4766 0.160 Uiso 1 1 calc R . .
H7B H 0.5085 0.5042 0.6461 0.160 Uiso 1 1 calc R . .
H7C H 0.6011 0.6859 0.5980 0.160 Uiso 1 1 calc R . .
C8 C -0.1376(12) 0.9630(12) 0.5176(10) 0.096(2) Uani 1 1 d DU . .
H8A H -0.1566 0.9895 0.4238 0.115 Uiso 1 1 calc R . .
C9 C -0.2610(12) 1.0045(12) 0.6175(10) 0.098(2) Uani 1 1 d DU . .
H9A H -0.2385 0.9738 0.7103 0.118 Uiso 1 1 calc R . .
C10 C -0.4306(5) 1.0922(6) 0.6085(5) 0.093(2) Uani 1 1 d GDU . .
C11 C -0.4801(6) 1.1532(7) 0.4756(4) 0.093(2) Uani 1 1 d GDU . .
H11A H -0.4035 1.1386 0.3892 0.112 Uiso 1 1 calc R . .
C12 C -0.6442(7) 1.2360(9) 0.4719(5) 0.096(2) Uani 1 1 d GDU . .
H12A H -0.6773 1.2768 0.3829 0.116 Uiso 1 1 calc R . .
C13 C -0.7587(6) 1.2579(9) 0.6010(7) 0.093(2) Uani 1 1 d GDU . .
C14 C -0.7092(6) 1.1969(9) 0.7339(6) 0.096(2) Uani 1 1 d GDU . .
H14A H -0.7859 1.2115 0.8203 0.115 Uiso 1 1 calc R . .
C15 C -0.5452(6) 1.1141(7) 0.7376(4) 0.101(3) Uani 1 1 d GDU . .
H15A H -0.5121 1.0733 0.8265 0.121 Uiso 1 1 calc R . .
C16 C -1.0494(13) 1.3490(14) 0.7398(10) 0.116(4) Uani 1 1 d DU . .
H16A H -0.9897 1.3944 0.7916 0.173 Uiso 1 1 calc R . .
H16B H -1.0940 1.2336 0.8018 0.173 Uiso 1 1 calc R . .
H16C H -1.1463 1.4265 0.7167 0.173 Uiso 1 1 calc R . .
C17 C -0.9797(12) 1.4056(14) 0.4672(9) 0.110(3) Uani 1 1 d DU . .
H17A H -0.9686 1.3149 0.4225 0.165 Uiso 1 1 calc R . .
H17B H -0.9065 1.5035 0.3991 0.165 Uiso 1 1 calc R . .
H17C H -1.1013 1.4444 0.4899 0.165 Uiso 1 1 calc R . .
N2 N -0.9243(10) 1.3373(11) 0.6012(7) 0.105(2) Uani 1 1 d DU . .
O3 O 0.9329(10) 1.0215(9) 0.1122(8) 0.137(3) Uani 1 1 d DU . .
C10' C 1.1798(6) 0.7288(6) 0.0645(4) 0.115(2) Uani 1 1 d GDU . .
H10A H 1.2316 0.8356 0.0458 0.138 Uiso 1 1 calc R . .
C1' C 0.9963(6) 0.7177(7) 0.0988(4) 0.096(2) Uani 1 1 d GDU . .
C2' C 0.9188(6) 0.5581(8) 0.1268(6) 0.121(3) Uani 1 1 d GDU . .
H2'A H 0.7961 0.5507 0.1498 0.146 Uiso 1 1 calc R . .
C3' C 1.0249(8) 0.4097(7) 0.1203(6) 0.126(3) Uani 1 1 d GDU . .
H3'A H 0.9731 0.3029 0.1390 0.151 Uiso 1 1 calc R . .
C4' C 1.2084(8) 0.4208(6) 0.0859(6) 0.111(2) Uani 1 1 d GDU . .
C9' C 1.2859(6) 0.5804(6) 0.0580(5) 0.116(2) Uani 1 1 d GDU . .
C5' C 1.3105(9) 0.2703(9) 0.0765(9) 0.127(3) Uani 1 1 d DU . .
H5'A H 1.2565 0.1660 0.0917 0.152 Uiso 1 1 calc R . .
C6' C 1.4964(9) 0.2782(9) 0.0439(9) 0.134(3) Uani 1 1 d DU . .
H6'A H 1.5676 0.1785 0.0420 0.160 Uiso 1 1 calc R . .
C7' C 1.5698(10) 0.4401(9) 0.0146(10) 0.133(3) Uani 1 1 d DU . .
H7'A H 1.6927 0.4491 -0.0116 0.159 Uiso 1 1 calc R . .
C8' C 1.4671(9) 0.5868(10) 0.0229(9) 0.130(3) Uani 1 1 d DU . .
H8'A H 1.5212 0.6923 0.0044 0.156 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S 0.1054(14) 0.1290(15) 0.0627(10) -0.0267(10) -0.0253(9) 0.0284(12)
O2 0.142(4) 0.160(5) 0.074(3) -0.034(3) -0.061(3) 0.051(4)
O1 0.132(6) 0.241(8) 0.121(6) 0.018(6) -0.005(5) 0.022(6)
N1 0.084(3) 0.111(3) 0.065(3) -0.010(3) -0.025(3) -0.026(3)
C2 0.093(4) 0.124(4) 0.058(3) -0.014(3) -0.018(3) -0.014(4)
C3 0.083(4) 0.125(4) 0.060(3) -0.015(3) -0.020(3) -0.016(4)
C4 0.084(3) 0.116(4) 0.066(3) -0.017(3) -0.017(3) -0.012(3)
C5 0.100(4) 0.120(4) 0.065(3) -0.025(3) -0.013(3) -0.010(4)
C6 0.096(4) 0.115(4) 0.061(3) -0.018(3) -0.019(3) -0.016(4)
C7 0.075(5) 0.122(6) 0.105(6) -0.005(5) -0.036(4) 0.003(5)
C8 0.094(4) 0.119(4) 0.065(3) -0.019(3) -0.015(3) -0.014(4)
C9 0.092(4) 0.119(4) 0.073(4) -0.023(3) -0.013(3) -0.008(4)
C10 0.085(3) 0.119(4) 0.066(3) -0.018(3) -0.023(3) -0.002(3)
C11 0.091(4) 0.127(4) 0.048(3) -0.022(3) -0.009(3) 0.003(4)
C12 0.092(4) 0.140(4) 0.046(3) -0.014(3) -0.020(3) -0.002(4)
C13 0.092(3) 0.135(4) 0.042(3) -0.017(3) -0.020(3) 0.003(3)
C14 0.100(4) 0.130(4) 0.047(3) -0.018(3) -0.017(3) 0.005(4)
C15 0.093(4) 0.132(4) 0.060(4) -0.013(4) -0.019(3) 0.005(4)
C16 0.096(6) 0.140(7) 0.077(5) -0.010(5) -0.009(5) 0.009(6)
C17 0.091(5) 0.165(7) 0.061(4) -0.019(5) -0.026(4) 0.006(6)
N2 0.103(4) 0.149(4) 0.045(3) -0.013(3) -0.017(3) 0.003(4)
O3 0.182(6) 0.118(5) 0.133(5) -0.047(4) -0.071(4) 0.008(5)
C10' 0.143(4) 0.151(4) 0.049(3) -0.033(3) -0.032(3) 0.031(4)
C1' 0.126(3) 0.136(4) 0.040(2) -0.031(3) -0.046(3) 0.020(3)
C2' 0.147(4) 0.160(5) 0.059(3) -0.028(4) -0.046(3) 0.017(4)
C3' 0.145(4) 0.174(5) 0.059(3) -0.028(4) -0.046(3) 0.018(4)
C4' 0.135(4) 0.162(4) 0.044(3) -0.035(3) -0.045(3) 0.029(4)
C9' 0.146(4) 0.157(4) 0.048(3) -0.042(3) -0.036(3) 0.039(4)
C5' 0.160(5) 0.174(5) 0.063(3) -0.048(3) -0.048(3) 0.014(4)
C6' 0.160(5) 0.179(5) 0.070(3) -0.045(4) -0.051(4) 0.034(5)
C7' 0.153(5) 0.180(5) 0.074(3) -0.045(4) -0.050(4) 0.028(5)
C8' 0.155(5) 0.175(5) 0.063(3) -0.046(4) -0.038(4) 0.027(5)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
S O1 1.435(8) . ?
S O3 1.449(7) . ?
S O2 1.497(6) . ?
S C1' 1.675(5) . ?
N1 C2 1.3900 . ?
N1 C6 1.3900 . ?
N1 C7 1.476(9) . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C4 C8 1.484(10) . ?
C5 C6 1.3900 . ?
C8 C9 1.279(12) . ?
C9 C10 1.451(10) . ?
C10 C11 1.3900 . ?
C10 C15 1.3900 . ?
C11 C12 1.3900 . ?
C12 C13 1.3900 . ?
C13 C14 1.3900 . ?
C13 N2 1.386(9) . ?
C14 C15 1.3900 . ?
C16 N2 1.466(11) . ?
C17 N2 1.425(11) . ?
C10' C1' 1.3900 . ?
C10' C9' 1.3900 . ?
C1' C2' 1.3900 . ?
C2' C3' 1.3900 . ?
C3' C4' 1.3900 . ?
C4' C9' 1.3900 . ?
C4' C5' 1.394(8) . ?
C9' C8' 1.369(8) . ?
C5' C6' 1.407(8) . ?
C6' C7' 1.388(9) . ?
C7' C8' 1.369(9) . ?

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
O1 S O3 112.3(6) . . ?
O1 S O2 114.2(5) . . ?
O3 S O2 109.4(4) . . ?
O1 S C1' 109.4(5) . . ?
O3 S C1' 105.1(4) . . ?
O2 S C1' 105.8(3) . . ?
C2 N1 C6 120.0 . . ?
C2 N1 C7 117.7(5) . . ?
C6 N1 C7 122.3(5) . . ?
C3 C2 N1 120.0 . . ?
C2 C3 C4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 C8 123.1(5) . . ?
C3 C4 C8 116.9(5) . . ?
C4 C5 C6 120.0 . . ?
C5 C6 N1 120.0 . . ?
C9 C8 C4 125.3(8) . . ?
C8 C9 C10 130.0(9) . . ?
C11 C10 C15 120.0 . . ?
C11 C10 C9 121.8(5) . . ?
C15 C10 C9 118.2(5) . . ?
C12 C11 C10 120.0 . . ?
C11 C12 C13 120.0 . . ?
C14 C13 C12 120.0 . . ?
C14 C13 N2 118.7(5) . . ?
C12 C13 N2 121.3(5) . . ?
C13 C14 C15 120.0 . . ?
C14 C15 C10 120.0 . . ?
C13 N2 C17 120.9(7) . . ?
C13 N2 C16 121.0(7) . . ?
C17 N2 C16 118.1(8) . . ?
C1' C10' C9' 120.0 . . ?
C2' C1' C10' 120.0 . . ?
C2' C1' S 110.6(3) . . ?
C10' C1' S 129.4(3) . . ?
C1' C2' C3' 120.0 . . ?
C2' C3' C4' 120.0 . . ?
C9' C4' C3' 120.0 . . ?
C9' C4' C5' 121.7(4) . . ?
C3' C4' C5' 118.3(4) . . ?
C8' C9' C4' 118.4(4) . . ?
C8' C9' C10' 121.6(4) . . ?
C4' C9' C10' 120.0 . . ?
C4' C5' C6' 119.1(6) . . ?
C7' C6' C5' 117.7(6) . . ?
C8' C7' C6' 122.1(6) . . ?
C7' C8' C9' 120.9(6) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        72.33
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.081