#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006937.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2006937
loop_
_publ_author_name
'Zhang, D.-C.'
'Zhang, T.-Z.'
'Zhang, Y.-Q.'
'Ge, L.-Q.'
'Yu, K.-B.'
_publ_section_title
;
 4-[2-(3,4-Dimethoxyphenyl)ethenyl]-1-methylpyridinium
 Tetrafluoroborate
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              138
_journal_page_last               140
_journal_volume                  54
_journal_year                    1998
_chemical_formula_iupac          'C16 H18 N O2 + , B F4 -'
_chemical_formula_structural     (CH3O)2C6H3C2H2C5H4NCH3.BF4
_chemical_formula_sum            'C16 H18 B F4 N O2'
_chemical_formula_weight         343.12
_chemical_melting_point          467.5(5)
_chemical_name_common
'  3', 4'-dimethoxy-N-methyl-4-stilbazolium  tetrafluoroborate'
_chemical_name_systematic
;
'4-[2-(3,4-dimethoxyphenyl)ethenyl]-1-methylpyridinium tetrafluoroborate'
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.5174(14)
_cell_length_b                   13.9190(13)
_cell_length_c                   17.0708(15)
_cell_measurement_reflns_used    46
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      17.86
_cell_measurement_theta_min      4.62
_cell_volume                     3211.8(5)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        'SHELXL93 (Sheldrick, 1993)'
_computing_molecular_graphics    SHELXL93
_computing_publication_material  SHELXL93
_computing_structure_refinement  SHELXL93
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       \w
_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  0.0113
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            3569
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.39
_diffrn_standards_decay_%        1.38
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_type   psi_scan_(SHELXL93;_Sheldrick,_1993)
_exptl_crystal_colour            brown-yellow
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.70
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.142
_refine_ls_extinction_coef       0.0026(4)
_refine_ls_extinction_method     SHELXL93_(Sheldrick,_1993)
_refine_ls_goodness_of_fit_all   0.891
_refine_ls_goodness_of_fit_obs   1.085
_refine_ls_hydrogen_treatment    'H atoms refined isotropically'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         2821
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.891
_refine_ls_restrained_S_obs      1.085
_refine_ls_R_factor_all          0.071
_refine_ls_R_factor_obs          0.038
_refine_ls_shift/esd_max         0.023
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0607P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.103
_refine_ls_wR_factor_obs         0.094
_reflns_number_observed          1688
_reflns_number_total             2821
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    ka1254.cif
_[local]_cod_data_source_block   y487
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '467-468K' was changed to '467.5(5)'
- the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2006937
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
F1 0.0705(9) 0.1433(14) 0.0604(8) 0.0072(9) -0.0090(7) 0.0115(9)
F2 0.1136(12) 0.0687(10) 0.0826(10) -0.0060(9) 0.0065(9) 0.0088(8)
F3 0.0687(8) 0.1224(12) 0.0547(8) -0.0014(8) 0.0131(7) -0.0081(8)
F4 0.0945(11) 0.0769(9) 0.0624(8) -0.0047(8) 0.0063(8) -0.0160(7)
O1 0.0740(10) 0.0402(8) 0.0458(8) 0.0053(7) -0.0009(7) -0.0081(6)
O2 0.0970(12) 0.0381(8) 0.0386(7) 0.0007(8) 0.0080(8) 0.0003(7)
N 0.0450(9) 0.0354(9) 0.0511(10) -0.0005(7) 0.0047(8) 0.0015(8)
B 0.0454(13) 0.0472(13) 0.0216(9) 0.0003(11) -0.0008(10) 0.0023(10)
C1 0.065(2) 0.0351(12) 0.079(2) -0.0030(12) 0.008(2) -0.0026(12)
C2 0.0505(13) 0.0430(12) 0.0466(12) -0.0011(10) 0.0027(10) 0.0078(10)
C3 0.0547(13) 0.0421(13) 0.0370(11) 0.0033(10) 0.0009(10) 0.0031(9)
C4 0.0396(11) 0.0403(11) 0.0399(10) 0.0001(9) 0.0025(9) 0.0028(9)
C5 0.0708(15) 0.0413(13) 0.0391(11) 0.0003(11) 0.0037(11) 0.0047(10)
C6 0.0667(15) 0.0464(13) 0.0437(12) -0.0035(11) 0.0002(11) -0.0017(11)
C7 0.0510(12) 0.0405(11) 0.0415(11) 0.0004(10) 0.0003(10) 0.0040(10)
C8 0.0464(12) 0.0428(12) 0.0399(11) -0.0010(10) -0.0001(10) 0.0030(10)
C9 0.0419(12) 0.0405(11) 0.0383(10) -0.0010(9) -0.0001(9) -0.0015(9)
C10 0.0581(13) 0.0422(12) 0.0390(11) -0.0037(10) 0.0039(10) 0.0043(10)
C11 0.0538(13) 0.0512(13) 0.0342(10) 0.0010(10) 0.0026(9) -0.0029(10)
C12 0.0434(11) 0.0378(11) 0.0415(11) 0.0031(9) -0.0027(9) -0.0064(9)
C13 0.0470(11) 0.0384(11) 0.0370(10) -0.0012(10) 0.0003(9) 0.0024(9)
C14 0.0482(12) 0.0409(12) 0.0323(10) 0.0014(9) 0.0023(10) -0.0019(9)
C15 0.080(2) 0.048(2) 0.0562(14) 0.0024(15) 0.0018(14) -0.0176(13)
C16 0.107(2) 0.0499(15) 0.0406(13) 0.002(2) 0.0081(15) 0.0047(12)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
F1 0.19503(10) 0.07754(12) 0.75908(8) 0.0914(5) Uani d 1 F
F2 0.12273(11) 0.18519(10) 0.68038(8) 0.0883(5) Uani d 1 F
F3 0.03127(10) 0.09901(10) 0.76459(7) 0.0819(5) Uani d 1 F
F4 0.09881(11) 0.02890(10) 0.65907(7) 0.0780(4) Uani d 1 F
O1 0.37070(10) 0.23529(9) 0.54918(8) 0.0533(4) Uani d 1 O
O2 0.40256(11) 0.17183(9) 0.40975(7) 0.0579(4) Uani d 1 O
N 0.37381(11) -0.51036(11) 0.39984(9) 0.0438(4) Uani d 1 N
B 0.1127(2) 0.0980(2) 0.71650(11) 0.0381(5) Uani d 1 B
C1 0.3732(2) -0.6159(2) 0.3891(2) 0.0597(7) Uani d 1 C
C2 0.3757(2) -0.4727(2) 0.47253(12) 0.0467(5) Uani d 1 C
C3 0.3770(2) -0.37717(14) 0.48485(12) 0.0446(5) Uani d 1 C
C4 0.37605(13) -0.31286(13) 0.42186(11) 0.0399(5) Uani d 1 C
C5 0.3746(2) -0.3542(2) 0.34743(12) 0.0504(5) Uani d 1 C
C6 0.3744(2) -0.4513(2) 0.33763(12) 0.0523(6) Uani d 1 C
C7 0.37690(15) -0.20956(14) 0.43110(12) 0.0443(5) Uani d 1 C
C8 0.36492(14) -0.16323(14) 0.49861(12) 0.0430(5) Uani d 1 C
C9 0.36415(14) -0.06000(13) 0.51099(10) 0.0402(5) Uani d 1 C
C10 0.3462(2) -0.02392(15) 0.58519(12) 0.0464(5) Uani d 1 C
C11 0.3474(2) 0.07388(15) 0.60012(12) 0.0464(5) Uani d 1 C
C12 0.36704(14) 0.13779(13) 0.54105(10) 0.0409(5) Uani d 1 C
C13 0.38416(14) 0.10274(13) 0.46433(10) 0.0408(5) Uani d 1 C
C14 0.38250(15) 0.00606(13) 0.45008(11) 0.0404(5) Uani d 1 C
C15 0.3627(2) 0.2716(2) 0.6273(2) 0.0617(7) Uani d 1 C
C16 0.4204(3) 0.1407(2) 0.33127(13) 0.0658(7) Uani d 1 C
H1A 0.331(2) -0.630(2) 0.3458(18) 0.121(12) Uiso d 1 H
H1B 0.434(2) -0.637(2) 0.3750(18) 0.132(13) Uiso d 1 H
H1C 0.349(3) -0.647(3) 0.437(2) 0.169(15) Uiso d 1 H
H2 0.3755(13) -0.5201(14) 0.5126(11) 0.050(6) Uiso d 1 H
H3 0.3794(13) -0.3560(13) 0.5369(11) 0.045(5) Uiso d 1 H
H5 0.3778(13) -0.3146(14) 0.3032(11) 0.053(6) Uiso d 1 H
H6 0.3686(15) -0.4821(15) 0.2866(12) 0.068(7) Uiso d 1 H
H7 0.3819(13) -0.1731(14) 0.3839(11) 0.053(6) Uiso d 1 H
H8 0.3572(13) -0.1999(14) 0.5461(11) 0.051(6) Uiso d 1 H
H10 0.3314(13) -0.0656(13) 0.6228(11) 0.044(5) Uiso d 1 H
H11 0.3363(14) 0.0962(13) 0.6530(12) 0.053(6) Uiso d 1 H
H14 0.3976(12) -0.0141(12) 0.4024(10) 0.034(5) Uiso d 1 H
H15A 0.3714(15) 0.3365(19) 0.6256(13) 0.067(7) Uiso d 1 H
H15B 0.4141(17) 0.2441(16) 0.6635(14) 0.083(8) Uiso d 1 H
H15C 0.2947(17) 0.2575(16) 0.6493(14) 0.084(8) Uiso d 1 H
H16A 0.3604(18) 0.1138(18) 0.3064(15) 0.088(9) Uiso d 1 H
H16B 0.4734(18) 0.0956(16) 0.3267(13) 0.080(8) Uiso d 1 H
H16C 0.4341(15) 0.2005(17) 0.3012(12) 0.073(7) Uiso d 1 H
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'
B B 0.0013 0.0007 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C12 O1 C15 116.3(2) y
C13 O2 C16 117.3(2) y
C6 N C2 119.4(2) y
C6 N C1 120.6(2) y
C2 N C1 120.0(2) y
F1 B F2 110.2(2) y
F1 B F3 109.80(15) y
F2 B F3 109.9(2) y
F1 B F4 110.1(2) y
F2 B F4 108.07(15) y
F3 B F4 108.7(2) y
C3 C2 N 121.9(2) y
C2 C3 C4 120.8(2) ?
C5 C4 C3 115.9(2) ?
C5 C4 C7 120.6(2) ?
C3 C4 C7 123.5(2) ?
C6 C5 C4 121.4(2) ?
N C6 C5 120.7(2) ?
C8 C7 C4 125.1(2) y
C7 C8 C9 127.3(2) y
C10 C9 C14 118.0(2) ?
C10 C9 C8 119.6(2) ?
C14 C9 C8 122.5(2) y
C9 C10 C11 121.5(2) ?
C12 C11 C10 120.3(2) ?
O1 C12 C11 125.3(2) ?
O1 C12 C13 115.5(2) ?
C11 C12 C13 119.2(2) ?
O2 C13 C14 125.2(2) ?
O2 C13 C12 114.8(2) ?
C14 C13 C12 120.0(2) ?
C13 C14 C9 120.9(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F1 B 1.360(2) y
F2 B 1.368(2) y
F3 B 1.373(2) y
F4 B 1.387(2) y
O1 C12 1.365(2) y
O1 C15 1.430(3) y
O2 C13 1.362(2) y
O2 C16 1.429(2) y
N C6 1.343(2) y
N C2 1.347(2) y
N C1 1.480(3) y
C2 C3 1.347(3) ?
C3 C4 1.399(3) ?
C4 C5 1.395(3) ?
C4 C7 1.447(3) y
C5 C6 1.363(3) ?
C7 C8 1.331(3) y
C8 C9 1.452(3) y
C9 C10 1.384(3) ?
C9 C14 1.410(2) ?
C10 C11 1.385(3) ?
C11 C12 1.371(3) ?
C12 C13 1.417(2) ?
C13 C14 1.368(3) ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
N F4 3.214(5) 4_546 yes
C6 F4 3.220(5) 4_546 yes
C3 F4 3.265(6) 8_655 yes
C7 O1 3.447(5) 5_656 yes
C8 O2 3.513(5) 5_656 yes
C9 C13 3.479(5) 5_656 yes
C9 C2 3.524(5) 8_665 yes
C12 C3 3.442(6) 8_665 yes
C14 C2 3.524(6) 8_665 yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C1 H1A F1 7_555 2.47(3) 3.318(5) 148(3) yes
C6 H6 F1 7_555 2.74(2) 3.281(4) 116(2) yes
C3 H3 F2 8_655 2.52(2) 3.449(7) 174(2) yes
C7 H7 F3 2_554 2.57(2) 3.462(5) 156(2) yes
C2 H2 F4 8_655 2.62(2) 3.203(7) 120.0(10) yes
C3 H3 F4 8_655 2.65(2) 3.265(6) 124.0(10) yes
C1 H1B F3 4_546 2.77(3) 3.392(6) 126(2) yes
C1 H1C O1 1_545 2.53(4) 3.429(6) 151(3) yes
C1 H1C O2 1_545 2.66(4) 3.002(5) 101(2) yes
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_publ_flag
C6 N C2 C3 0.8(3) ?
C1 N C2 C3 179.5(2) ?
N C2 C3 C4 0.3(3) ?
C2 C3 C4 C5 -0.6(3) ?
C2 C3 C4 C7 179.7(2) ?
C3 C4 C5 C6 -0.1(3) ?
C7 C4 C5 C6 179.6(2) ?
C2 N C6 C5 -1.5(3) ?
C1 N C6 C5 179.8(2) ?
C4 C5 C6 N 1.1(4) ?
C5 C4 C7 C8 170.5(2) y
C3 C4 C7 C8 -9.8(3) ?
C4 C7 C8 C9 -179.3(2) y
C7 C8 C9 C10 177.1(2) ?
C7 C8 C9 C14 -3.8(3) y
C14 C9 C10 C11 -0.9(3) ?
C8 C9 C10 C11 178.2(2) ?
C9 C10 C11 C12 -0.3(3) ?
C15 O1 C12 C11 6.4(3) y
C15 O1 C12 C13 -174.4(2) y
C10 C11 C12 O1 -179.6(2) ?
C10 C11 C12 C13 1.2(3) ?
C16 O2 C13 C14 0.7(3) y
C16 O2 C13 C12 180.0(2) y
O1 C12 C13 O2 0.4(2) ?
C11 C12 C13 O2 179.7(2) ?
O1 C12 C13 C14 179.7(2) ?
C11 C12 C13 C14 -1.0(3) ?
O2 C13 C14 C9 179.0(2) ?
C12 C13 C14 C9 -0.2(3) ?
C10 C9 C14 C13 1.1(3) ?
C8 C9 C14 C13 -178.0(2) ?