# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2010


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_address     
;
Division of Energy Systems Research and Department of Chemistry
Ajou University
Suwon 443-749
Republic of Korea
;
_publ_contact_author_email       hsyun@ajou.ac.kr
_publ_contact_author_fax         82-31-219-1615
_publ_contact_author_phone       82-31-219-2605
#=============================================
# SUBMISSION DETAILS
_publ_contact_author_name        
'Hoseop Yun' # Name of author for correspondence
_publ_author_name                O.Kwon

data_P-16
_database_code_depnum_ccdc_archive 'CCDC 761254'
_audit_update_record             
;
2009-12-01 # Formatted by publCIF
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_name_systematic        
;
4-(4-(dimethylamino)styryl)-1-(2,5-dimethylbenzyl)pyridinium
4-methylbenzenesulfonate
;
_chemical_formula_sum            'C31 H34 N2 O3 S'
_chemical_formula_weight         514.66
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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a                   7.6688(3)
_cell_length_b                   15.1880(6)
_cell_length_c                   11.8332(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.3468(11)
_cell_angle_gamma                90.00
_cell_volume                     1351.32(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(1)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      24.99
_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             548
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_diffrn_ambient_temperature      290(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-axis Rapid S'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10620
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         24.99
_reflns_number_total             4726
_reflns_number_gt                3866
_reflns_threshold_expression     >2\s(I)
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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^ > 2\s(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^)+(0.0493P)^2^+0.1019P] 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     SHELXL
_refine_ls_extinction_coef       0.0097(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(7)
_refine_ls_number_reflns         4726
_refine_ls_number_parameters     335
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.000
_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
S1 S 1.43740(8) 0.79691(4) 0.83642(5) 0.04822(17) Uani 1 1 d . . .
O1 O 1.5104(2) 0.86599(13) 0.77467(17) 0.0637(5) Uani 1 1 d . . .
O2 O 1.3933(3) 0.82726(13) 0.94332(16) 0.0683(6) Uani 1 1 d . . .
O3 O 1.5448(2) 0.71803(12) 0.84922(18) 0.0658(5) Uani 1 1 d . . .
N1 N 2.2004(3) 0.65298(15) 1.2922(2) 0.0625(6) Uani 1 1 d . . .
N2 N 0.8321(3) 0.52043(13) 0.91879(17) 0.0441(5) Uani 1 1 d . . .
C1 C 2.2911(5) 0.7358(2) 1.2931(4) 0.0945(12) Uani 1 1 d . . .
H1A H 2.4137 0.7286 1.3293 0.142 Uiso 1 1 calc R . .
H1B H 2.2366 0.7783 1.3352 0.142 Uiso 1 1 calc R . .
H1C H 2.2835 0.7559 1.2153 0.142 Uiso 1 1 calc R . .
C2 C 2.3009(4) 0.5793(2) 1.3502(3) 0.0729(9) Uani 1 1 d . . .
H2A H 2.4223 0.5967 1.3770 0.109 Uiso 1 1 calc R . .
H2B H 2.2966 0.5310 1.2973 0.109 Uiso 1 1 calc R . .
H2C H 2.2503 0.5614 1.4146 0.109 Uiso 1 1 calc R . .
C3 C 2.0238(3) 0.64586(17) 1.2464(2) 0.0496(6) Uani 1 1 d . . .
C4 C 1.9332(3) 0.56518(17) 1.2440(2) 0.0507(6) Uani 1 1 d . . .
H4 H 1.9941 0.5157 1.2773 0.061 Uiso 1 1 calc R . .
C5 C 1.7561(3) 0.55795(18) 1.1936(2) 0.0534(6) Uani 1 1 d . . .
H5 H 1.7002 0.5037 1.1944 0.064 Uiso 1 1 calc R . .
C6 C 1.6579(3) 0.62915(17) 1.1413(2) 0.0486(6) Uani 1 1 d . . .
C7 C 1.7444(4) 0.70847(18) 1.1452(2) 0.0580(7) Uani 1 1 d . . .
H7 H 1.6813 0.7575 1.1126 0.070 Uiso 1 1 calc R . .
C8 C 1.9212(4) 0.71822(18) 1.1954(2) 0.0585(7) Uani 1 1 d . . .
H8 H 1.9741 0.7733 1.1958 0.070 Uiso 1 1 calc R . .
C9 C 1.4719(3) 0.62170(17) 1.0838(2) 0.0499(6) Uani 1 1 d . . .
H9 H 1.4161 0.6728 1.0518 0.060 Uiso 1 1 calc R . .
C10 C 1.3743(3) 0.54812(17) 1.0730(2) 0.0503(6) Uani 1 1 d . . .
H10 H 1.4305 0.4967 1.1036 0.060 Uiso 1 1 calc R . .
C11 C 1.1889(3) 0.54158(16) 1.0177(2) 0.0449(6) Uani 1 1 d . . .
C12 C 1.0846(3) 0.61166(17) 0.9649(2) 0.0512(6) Uani 1 1 d . . .
H12 H 1.1359 0.6669 0.9623 0.061 Uiso 1 1 calc R . .
C13 C 0.9103(4) 0.60020(17) 0.9176(2) 0.0508(6) Uani 1 1 d . . .
H13 H 0.8434 0.6478 0.8839 0.061 Uiso 1 1 calc R . .
C14 C 0.9283(3) 0.45015(17) 0.9667(2) 0.0498(6) Uani 1 1 d . . .
H14 H 0.8743 0.3953 0.9665 0.060 Uiso 1 1 calc R . .
C15 C 1.1035(3) 0.45963(16) 1.0152(2) 0.0492(6) Uani 1 1 d . . .
H15 H 1.1681 0.4108 1.0474 0.059 Uiso 1 1 calc R . .
C16 C 0.6430(3) 0.50823(19) 0.8670(2) 0.0502(6) Uani 1 1 d . . .
H16A H 0.5814 0.5637 0.8697 0.060 Uiso 1 1 calc R . .
H16B H 0.5920 0.4660 0.9127 0.060 Uiso 1 1 calc R . .
C17 C 0.6116(3) 0.47651(15) 0.7435(2) 0.0414(5) Uani 1 1 d . . .
C18 C 0.4392(3) 0.45028(17) 0.6922(2) 0.0497(6) Uani 1 1 d . . .
C19 C 0.4092(3) 0.42153(19) 0.5789(2) 0.0611(7) Uani 1 1 d . . .
H19 H 0.2953 0.4038 0.5438 0.073 Uiso 1 1 calc R . .
C20 C 0.5436(4) 0.41851(17) 0.5165(2) 0.0544(7) Uani 1 1 d . . .
H20 H 0.5193 0.3986 0.4407 0.065 Uiso 1 1 calc R . .
C21 C 0.7130(3) 0.44474(17) 0.5660(2) 0.0480(6) Uani 1 1 d . . .
C22 C 0.7452(3) 0.47341(17) 0.6797(2) 0.0464(6) Uani 1 1 d . . .
H22 H 0.8595 0.4910 0.7140 0.056 Uiso 1 1 calc R . .
C23 C 0.2896(4) 0.4532(2) 0.7597(3) 0.0745(9) Uani 1 1 d . . .
H23A H 0.3353 0.4740 0.8364 0.112 Uiso 1 1 calc R . .
H23B H 0.2413 0.3952 0.7632 0.112 Uiso 1 1 calc R . .
H23C H 0.1979 0.4922 0.7220 0.112 Uiso 1 1 calc R . .
C24 C 0.8619(4) 0.4391(2) 0.4998(3) 0.0739(9) Uani 1 1 d . . .
H24A H 0.9701 0.4601 0.5473 0.111 Uiso 1 1 calc R . .
H24B H 0.8332 0.4747 0.4316 0.111 Uiso 1 1 calc R . .
H24C H 0.8770 0.3790 0.4785 0.111 Uiso 1 1 calc R . .
C31 C 0.9082(4) 0.7198(2) 0.6040(3) 0.0651(8) Uani 1 1 d . . .
C32 C 1.0682(4) 0.6852(2) 0.5879(3) 0.0788(9) Uani 1 1 d . . .
H32 H 1.0680 0.6458 0.5277 0.095 Uiso 1 1 calc R . .
C33 C 1.2285(4) 0.7072(2) 0.6583(3) 0.0658(8) Uani 1 1 d . . .
H33 H 1.3337 0.6823 0.6455 0.079 Uiso 1 1 calc R . .
C34 C 1.2320(3) 0.76625(15) 0.7476(2) 0.0443(6) Uani 1 1 d . . .
C35 C 1.0729(3) 0.8019(2) 0.7634(2) 0.0560(6) Uani 1 1 d . . .
H35 H 1.0732 0.8421 0.8227 0.067 Uiso 1 1 calc R . .
C36 C 0.9143(3) 0.7795(2) 0.6936(3) 0.0660(8) Uani 1 1 d . . .
H36 H 0.8094 0.8047 0.7065 0.079 Uiso 1 1 calc R . .
C37 C 0.7347(4) 0.6942(2) 0.5270(4) 0.1017(13) Uani 1 1 d . . .
H37A H 0.6383 0.7230 0.5529 0.153 Uiso 1 1 calc R . .
H37B H 0.7195 0.6316 0.5299 0.153 Uiso 1 1 calc R . .
H37C H 0.7361 0.7118 0.4493 0.153 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
S1 0.0509(3) 0.0458(3) 0.0459(3) 0.0010(3) 0.0044(3) 0.0086(3)
O1 0.0662(12) 0.0585(11) 0.0642(13) 0.0050(9) 0.0072(10) -0.0126(9)
O2 0.0804(13) 0.0772(14) 0.0448(11) -0.0076(9) 0.0062(9) 0.0194(10)
O3 0.0630(12) 0.0551(11) 0.0736(14) 0.0020(10) -0.0006(10) 0.0240(9)
N1 0.0538(14) 0.0575(15) 0.0703(16) -0.0063(12) -0.0022(12) -0.0019(11)
N2 0.0482(11) 0.0474(12) 0.0369(12) -0.0028(9) 0.0090(9) 0.0053(10)
C1 0.069(2) 0.073(2) 0.131(3) -0.021(2) -0.006(2) -0.0107(18)
C2 0.0602(18) 0.081(2) 0.072(2) 0.0046(17) 0.0000(15) 0.0082(16)
C3 0.0529(15) 0.0507(15) 0.0440(15) -0.0072(12) 0.0069(12) 0.0028(12)
C4 0.0562(16) 0.0461(14) 0.0483(15) 0.0052(12) 0.0064(12) 0.0058(12)
C5 0.0565(15) 0.0495(16) 0.0535(16) 0.0037(13) 0.0090(13) -0.0031(13)
C6 0.0540(14) 0.0477(14) 0.0432(14) -0.0025(11) 0.0072(11) 0.0000(12)
C7 0.0610(17) 0.0486(16) 0.0603(17) -0.0006(13) 0.0023(13) 0.0069(13)
C8 0.0626(17) 0.0422(14) 0.0679(18) -0.0031(13) 0.0062(14) -0.0010(13)
C9 0.0569(15) 0.0498(15) 0.0419(14) 0.0017(11) 0.0074(11) 0.0059(13)
C10 0.0550(15) 0.0522(15) 0.0440(15) 0.0035(12) 0.0108(12) 0.0080(13)
C11 0.0498(14) 0.0520(15) 0.0337(13) 0.0003(11) 0.0103(11) 0.0050(12)
C12 0.0558(15) 0.0461(14) 0.0506(15) 0.0016(12) 0.0073(12) -0.0002(12)
C13 0.0598(16) 0.0469(14) 0.0441(15) 0.0010(11) 0.0062(12) 0.0074(12)
C14 0.0580(15) 0.0460(14) 0.0469(14) 0.0038(12) 0.0137(12) 0.0043(12)
C15 0.0564(15) 0.0434(14) 0.0483(15) 0.0093(11) 0.0116(12) 0.0075(12)
C16 0.0429(13) 0.0603(16) 0.0493(16) -0.0030(13) 0.0133(11) 0.0049(12)
C17 0.0429(12) 0.0397(12) 0.0416(13) 0.0048(10) 0.0089(10) 0.0058(10)
C18 0.0429(13) 0.0535(15) 0.0523(15) 0.0023(12) 0.0087(11) 0.0043(11)
C19 0.0438(14) 0.0682(18) 0.066(2) -0.0093(14) -0.0015(13) -0.0042(13)
C20 0.0634(16) 0.0552(16) 0.0407(14) -0.0041(11) 0.0008(12) 0.0067(13)
C21 0.0540(14) 0.0513(14) 0.0393(13) 0.0002(12) 0.0108(11) 0.0025(12)
C22 0.0438(13) 0.0504(14) 0.0455(15) -0.0017(11) 0.0098(11) -0.0028(11)
C23 0.0425(14) 0.100(2) 0.083(2) -0.0116(19) 0.0179(14) -0.0040(16)
C24 0.078(2) 0.096(2) 0.0553(18) -0.0126(17) 0.0299(16) -0.0092(18)
C31 0.0521(16) 0.0567(17) 0.082(2) 0.0069(16) 0.0007(14) -0.0056(14)
C32 0.0618(18) 0.079(2) 0.090(2) -0.0333(19) 0.0021(16) -0.0025(16)
C33 0.0505(16) 0.0647(18) 0.082(2) -0.0203(16) 0.0127(14) 0.0030(14)
C34 0.0451(13) 0.0427(13) 0.0468(14) 0.0037(11) 0.0136(11) 0.0039(10)
C35 0.0568(14) 0.0628(16) 0.0504(14) 0.0002(15) 0.0154(12) 0.0127(15)
C36 0.0473(14) 0.081(2) 0.0717(19) 0.0153(16) 0.0165(14) 0.0176(15)
C37 0.062(2) 0.081(2) 0.146(4) 0.008(2) -0.020(2) -0.0092(18)
_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
S1 O3 1.4447(18) . ?
S1 O2 1.4476(19) . ?
S1 O1 1.4521(19) . ?
S1 C34 1.775(3) . ?
N1 C3 1.360(3) . ?
N1 C1 1.436(4) . ?
N1 C2 1.453(4) . ?
N2 C13 1.353(3) . ?
N2 C14 1.357(3) . ?
N2 C16 1.471(3) . ?
C3 C4 1.406(4) . ?
C3 C8 1.416(4) . ?
C4 C5 1.376(4) . ?
C5 C6 1.391(4) . ?
C6 C7 1.372(4) . ?
C6 C9 1.459(4) . ?
C7 C8 1.376(4) . ?
C9 C10 1.337(3) . ?
C10 C11 1.447(3) . ?
C11 C12 1.402(3) . ?
C11 C15 1.404(3) . ?
C12 C13 1.355(4) . ?
C14 C15 1.361(3) . ?
C16 C17 1.512(3) . ?
C17 C22 1.388(3) . ?
C17 C18 1.400(3) . ?
C18 C19 1.386(4) . ?
C18 C23 1.522(3) . ?
C19 C20 1.381(4) . ?
C20 C21 1.375(4) . ?
C21 C22 1.390(3) . ?
C21 C24 1.508(3) . ?
C31 C32 1.382(4) . ?
C31 C36 1.388(4) . ?
C31 C37 1.508(4) . ?
C32 C33 1.384(4) . ?
C33 C34 1.382(4) . ?
C34 C35 1.381(3) . ?
C35 C36 1.371(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
O3 S1 O2 113.51(12) . . ?
O3 S1 O1 112.57(12) . . ?
O2 S1 O1 112.90(12) . . ?
O3 S1 C34 105.41(11) . . ?
O2 S1 C34 105.55(12) . . ?
O1 S1 C34 106.06(11) . . ?
C3 N1 C1 121.0(2) . . ?
C3 N1 C2 121.4(2) . . ?
C1 N1 C2 117.4(2) . . ?
C13 N2 C14 120.2(2) . . ?
C13 N2 C16 120.7(2) . . ?
C14 N2 C16 119.0(2) . . ?
N1 C3 C4 121.8(2) . . ?
N1 C3 C8 122.3(2) . . ?
C4 C3 C8 115.9(2) . . ?
C5 C4 C3 121.3(2) . . ?
C4 C5 C6 122.2(2) . . ?
C7 C6 C5 116.9(2) . . ?
C7 C6 C9 120.4(2) . . ?
C5 C6 C9 122.8(2) . . ?
C6 C7 C8 122.5(3) . . ?
C7 C8 C3 121.2(3) . . ?
C10 C9 C6 125.9(2) . . ?
C9 C10 C11 125.6(2) . . ?
C12 C11 C15 116.1(2) . . ?
C12 C11 C10 125.0(2) . . ?
C15 C11 C10 118.9(2) . . ?
C13 C12 C11 121.1(2) . . ?
N2 C13 C12 120.9(2) . . ?
N2 C14 C15 120.2(2) . . ?
C14 C15 C11 121.4(2) . . ?
N2 C16 C17 113.55(18) . . ?
C22 C17 C18 119.3(2) . . ?
C22 C17 C16 122.8(2) . . ?
C18 C17 C16 117.85(19) . . ?
C19 C18 C17 118.2(2) . . ?
C19 C18 C23 121.2(2) . . ?
C17 C18 C23 120.6(2) . . ?
C20 C19 C18 121.9(2) . . ?
C21 C20 C19 120.3(2) . . ?
C20 C21 C22 118.4(2) . . ?
C20 C21 C24 120.8(2) . . ?
C22 C21 C24 120.8(2) . . ?
C17 C22 C21 121.9(2) . . ?
C32 C31 C36 117.1(3) . . ?
C32 C31 C37 121.3(3) . . ?
C36 C31 C37 121.5(3) . . ?
C31 C32 C33 122.2(3) . . ?
C34 C33 C32 119.9(3) . . ?
C35 C34 C33 118.2(2) . . ?
C35 C34 S1 121.5(2) . . ?
C33 C34 S1 120.29(18) . . ?
C36 C35 C34 121.6(3) . . ?
C35 C36 C31 121.0(3) . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.033