#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/13/2011302.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_2011302
loop_
_publ_author_name
'Li, Shu-Jin'
'Zhang, De-Chun'
'Huang, Zhong-Lin'
'Zhang, Yan-Qiu'
'Yu, Kai-Bei'
_publ_section_title
;
 4-[2-(4-Methoxyphenyl)ethenyl]-N-methylpyridinium
 tetraphenylborate
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1122
_journal_page_last               1123
_journal_paper_doi               10.1107/S0108270100007538
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C15 H16 N O + , C24 H20 B -'
_chemical_formula_sum            'C39 H36 B N O'
_chemical_formula_weight         545.50
_chemical_melting_point          509.5(5)
_chemical_name_common
;
N-methyl-4'-methoxy-4-stilbazolium tetraphenylborate
;
_chemical_name_systematic
;
4-[2-(4-methoxyphenyl)ethenyl]-N-methylpyridinum tetraphenylborate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.160(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.029(2)
_cell_length_b                   10.819(2)
_cell_length_c                   21.660(3)
_cell_measurement_reflns_used    26
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      17.23
_cell_measurement_theta_min      3.81
_cell_volume                     3014.3(8)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        'SHELXTL (Sheldrick, 1995)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full .999
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .010
_diffrn_reflns_av_sigmaI/netI    .040
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6502
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.58
_diffrn_standards_decay_%        2.74
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .070
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'XSCANS (Siemens, 1994)'
_exptl_crystal_colour            yellow-green
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_meas      ?
_exptl_crystal_description       granular
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          .60
_exptl_crystal_size_mid          .56
_exptl_crystal_size_min          .52
_refine_diff_density_max         .13
_refine_diff_density_min         -.11
_refine_ls_extinction_coef       .0103(7)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   .868
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         5318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .868
_refine_ls_R_factor_all          .070
_refine_ls_R_factor_gt           .036
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.047P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .088
_reflns_number_gt                3204
_reflns_number_total             5318
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            da1127.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '509-510' was changed to '509.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '509-510' was changed to '509.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2011302
_cod_database_fobs_code          2011302
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O .10266(9) .19999(12) .53477(6) .0769(4) Uani d . 1 . . O
N .29052(10) -.74021(13) .65390(6) .0595(4) Uani d . 1 . . N
B .69076(13) -.64864(16) .65696(7) .0442(4) Uani d . 1 . . B
C1 .33552(16) -.86130(17) .67301(8) .0823(6) Uani d . 1 . . C
H1A .3487 -.9059 .6368 .099 Uiso calc R 1 . . H
H1B .2877 -.9072 .6936 .099 Uiso calc R 1 . . H
H1C .3995 -.8500 .7012 .099 Uiso calc R 1 . . H
C2 .22191(14) -.68803(17) .68588(8) .0672(5) Uani d . 1 . . C
H2 .1996 -.7314 .7184 .081 Uiso calc R 1 . . H
C3 .18459(13) -.57303(18) .67152(8) .0665(5) Uani d . 1 . . C
H3 .1369 -.5388 .6943 .080 Uiso calc R 1 . . H
C4 .21622(12) -.50480(16) .62314(7) .0541(4) Uani d . 1 . . C
C5 .28438(12) -.56409(16) .58945(7) .0597(4) Uani d . 1 . . C
H5 .3053 -.5246 .5554 .072 Uiso calc R 1 . . H
C6 .32044(13) -.67866(17) .60586(7) .0638(5) Uani d . 1 . . C
H6 .3672 -.7158 .5833 .077 Uiso calc R 1 . . H
C7 .18011(13) -.37902(17) .61133(7) .0614(5) Uani d . 1 . . C
H7 .1262 -.3529 .6316 .074 Uiso calc R 1 . . H
C8 .21639(12) -.29757(16) .57449(7) .0590(4) Uani d . 1 . . C
H8 .2672 -.3256 .5522 .071 Uiso calc R 1 . . H
C9 .18524(12) -.16908(16) .56520(7) .0552(4) Uani d . 1 . . C
C10 .10596(13) -.11727(17) .59262(8) .0674(5) Uani d . 1 . . C
H10 .0718 -.1664 .6182 .081 Uiso calc R 1 . . H
C11 .07637(14) .00368(17) .58330(8) .0665(5) Uani d . 1 . . C
H11 .0228 .0354 .6023 .080 Uiso calc R 1 . . H
C12 .12592(13) .07825(17) .54584(7) .0591(4) Uani d . 1 . . C
C13 .20576(13) .02960(18) .51816(8) .0679(5) Uani d . 1 . . C
H13 .2400 .0795 .4930 .082 Uiso calc R 1 . . H
C14 .23460(13) -.09173(18) .52766(7) .0645(5) Uani d . 1 . . C
H14 .2882 -.1230 .5086 .077 Uiso calc R 1 . . H
C15 .01622(14) .25046(17) .55875(9) .0774(5) Uani d . 1 . . C
H15A -.0453 .2044 .5428 .093 Uiso calc R 1 . . H
H15B .0069 .3353 .5460 .093 Uiso calc R 1 . . H
H15C .0287 .2458 .6036 .093 Uiso calc R 1 . . H
C16 .61630(11) -.63389(13) .71136(6) .0420(3) Uani d . 1 . . C
C17 .63123(12) -.69754(14) .76809(7) .0549(4) Uani d . 1 . . C
H17 .6890 -.7487 .7773 .066 Uiso calc R 1 . . H
C18 .56405(14) -.68797(16) .81118(8) .0655(5) Uani d . 1 . . C
H18 .5767 -.7335 .8480 .079 Uiso calc R 1 . . H
C19 .47916(13) -.61218(16) .80010(8) .0632(5) Uani d . 1 . . C
H19 .4343 -.6054 .8293 .076 Uiso calc R 1 . . H
C20 .46104(12) -.54604(15) .74514(7) .0581(4) Uani d . 1 . . C
H20 .4042 -.4932 .7372 .070 Uiso calc R 1 . . H
C21 .52774(11) -.55848(14) .70190(7) .0497(4) Uani d . 1 . . C
H21 .5131 -.5146 .6646 .060 Uiso calc R 1 . . H
C22 .74043(11) -.51675(14) .63833(6) .0460(4) Uani d . 1 . . C
C23 .71699(12) -.39954(14) .65789(7) .0527(4) Uani d . 1 . . C
H23 .6677 -.3920 .6843 .063 Uiso calc R 1 . . H
C24 .76355(14) -.29307(15) .63989(8) .0642(5) Uani d . 1 . . C
H24 .7452 -.2167 .6545 .077 Uiso calc R 1 . . H
C25 .83580(14) -.29923(18) .60106(8) .0693(5) Uani d . 1 . . C
H25 .8671 -.2278 .5890 .083 Uiso calc R 1 . . H
C26 .86168(14) -.41300(19) .58002(8) .0759(5) Uani d . 1 . . C
H26 .9108 -.4190 .5533 .091 Uiso calc R 1 . . H
C27 .81494(13) -.51884(16) .59837(8) .0660(5) Uani d . 1 . . C
H27 .8339 -.5947 .5835 .079 Uiso calc R 1 . . H
C28 .61428(11) -.70558(13) .59592(6) .0441(4) Uani d . 1 . . C
C29 .58404(12) -.64129(14) .54018(6) .0523(4) Uani d . 1 . . C
H29 .6113 -.5628 .5362 .063 Uiso calc R 1 . . H
C30 .51534(13) -.68871(17) .49038(7) .0626(5) Uani d . 1 . . C
H30 .4968 -.6417 .4544 .075 Uiso calc R 1 . . H
C31 .47465(13) -.80478(18) .49410(8) .0653(5) Uani d . 1 . . C
H31 .4297 -.8378 .4605 .078 Uiso calc R 1 . . H
C32 .50112(12) -.87181(15) .54827(8) .0593(4) Uani d . 1 . . C
H32 .4740 -.9506 .5515 .071 Uiso calc R 1 . . H
C33 .56820(11) -.82186(14) .59802(7) .0503(4) Uani d . 1 . . C
H33 .5833 -.8679 .6346 .060 Uiso calc R 1 . . H
C34 .79047(11) -.73873(14) .68235(7) .0460(4) Uani d . 1 . . C
C35 .80708(12) -.85890(15) .66266(7) .0547(4) Uani d . 1 . . C
H35 .7582 -.8940 .6316 .066 Uiso calc R 1 . . H
C36 .89368(15) -.92842(17) .68753(9) .0668(5) Uani d . 1 . . C
H36 .9005 -1.0090 .6738 .080 Uiso calc R 1 . . H
C37 .96907(14) -.87920(19) .73217(9) .0705(5) Uani d . 1 . . C
H37 1.0274 -.9252 .7485 .085 Uiso calc R 1 . . H
C38 .95669(13) -.76085(18) .75218(8) .0663(5) Uani d . 1 . . C
H38 1.0074 -.7254 .7820 .080 Uiso calc R 1 . . H
C39 .86929(12) -.69418(15) .72819(7) .0578(4) Uani d . 1 . . C
H39 .8624 -.6148 .7435 .069 Uiso calc R 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B .0013 .0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 '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 O C15 118.24(14) y
C2 N C6 119.41(15) y
C2 N C1 119.98(15) y
C6 N C1 120.56(14) y
C22 B C28 109.87(12) y
C22 B C34 105.98(12) y
C28 B C34 113.07(12) y
C22 B C16 113.01(12) y
C28 B C16 105.12(11) y
C34 B C16 109.94(11) y
N C2 C3 120.88(16) ?
C2 C3 C4 121.34(16) ?
C5 C4 C3 116.02(16) ?
C5 C4 C7 123.80(15) ?
C3 C4 C7 120.16(15) ?
C6 C5 C4 120.54(15) ?
N C6 C5 121.72(15) ?
C8 C7 C4 126.42(16) y
C7 C8 C9 126.94(15) y
C10 C9 C14 116.80(17) ?
C10 C9 C8 122.48(15) ?
C14 C9 C8 120.71(15) ?
C11 C10 C9 122.23(16) ?
C10 C11 C12 119.97(16) ?
O C12 C11 123.91(16) ?
O C12 C13 116.88(16) ?
C11 C12 C13 119.20(17) ?
C14 C13 C12 120.37(16) ?
C13 C14 C9 121.42(16) ?
C17 C16 C21 114.35(13) ?
C17 C16 B 124.50(13) ?
C21 C16 B 121.08(12) ?
C18 C17 C16 122.94(15) ?
C19 C18 C17 120.55(15) ?
C18 C19 C20 119.09(15) ?
C19 C20 C21 119.71(15) ?
C20 C21 C16 123.34(14) ?
C23 C22 C27 114.32(14) ?
C23 C22 B 127.21(13) ?
C27 C22 B 118.47(14) ?
C22 C23 C24 123.13(15) ?
C25 C24 C23 120.67(17) ?
C24 C25 C26 118.68(17) ?
C25 C26 C27 120.24(16) ?
C26 C27 C22 122.97(16) ?
C29 C28 C33 114.42(14) ?
C29 C28 B 124.13(13) ?
C33 C28 B 121.31(13) ?
C30 C29 C28 123.21(15) ?
C31 C30 C29 120.09(16) ?
C30 C31 C32 119.11(16) ?
C31 C32 C33 119.97(16) ?
C32 C33 C28 123.17(15) ?
C39 C34 C35 114.00(14) ?
C39 C34 B 119.02(13) ?
C35 C34 B 126.98(14) ?
C36 C35 C34 122.74(16) ?
C37 C36 C35 120.59(17) ?
C38 C37 C36 118.61(17) ?
C37 C38 C39 120.13(18) ?
C38 C39 C34 123.90(16) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O C12 . 1.3642(19) y
O C15 . 1.4221(19) y
N C2 . 1.340(2) y
N C6 . 1.3443(19) y
N C1 . 1.468(2) y
B C22 . 1.643(2) n
B C28 . 1.643(2) n
B C34 . 1.647(2) n
B C16 . 1.649(2) n
C2 C3 . 1.354(2) ?
C3 C4 . 1.397(2) ?
C4 C5 . 1.392(2) ?
C4 C7 . 1.449(2) y
C5 C6 . 1.353(2) ?
C7 C8 . 1.325(2) y
C8 C9 . 1.453(2) y
C9 C10 . 1.389(2) ?
C9 C14 . 1.393(2) ?
C10 C11 . 1.370(2) ?
C11 C12 . 1.376(2) ?
C12 C13 . 1.385(2) ?
C13 C14 . 1.372(2) ?
C16 C17 . 1.3950(19) ?
C16 C21 . 1.4014(19) ?
C17 C18 . 1.381(2) ?
C18 C19 . 1.367(2) ?
C19 C20 . 1.377(2) ?
C20 C21 . 1.382(2) ?
C22 C23 . 1.386(2) ?
C22 C27 . 1.400(2) ?
C23 C24 . 1.386(2) ?
C24 C25 . 1.360(2) ?
C25 C26 . 1.373(2) ?
C26 C27 . 1.385(2) ?
C28 C29 . 1.3946(19) ?
C28 C33 . 1.398(2) ?
C29 C30 . 1.386(2) ?
C30 C31 . 1.370(2) ?
C31 C32 . 1.376(2) ?
C32 C33 . 1.385(2) ?
C34 C39 . 1.396(2) ?
C34 C35 . 1.396(2) ?
C35 C36 . 1.391(2) ?
C36 C37 . 1.371(2) ?
C37 C38 . 1.370(2) ?
C38 C39 . 1.378(2) ?
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 -1.8(2) ?
C1 N C2 C3 175.73(16) ?
N C2 C3 C4 -.1(3) ?
C2 C3 C4 C5 2.6(2) ?
C2 C3 C4 C7 -176.09(16) ?
C3 C4 C5 C6 -3.2(2) ?
C7 C4 C5 C6 175.39(16) ?
C2 N C6 C5 1.1(2) ?
C1 N C6 C5 -176.38(16) ?
C4 C5 C6 N 1.5(2) ?
C5 C4 C7 C8 -10.4(3) ?
C3 C4 C7 C8 168.18(16) y
C4 C7 C8 C9 -175.97(15) y
C7 C8 C9 C10 -3.9(3) y
C7 C8 C9 C14 176.17(16) y
C14 C9 C10 C11 .4(2) ?
C8 C9 C10 C11 -179.47(16) ?
C9 C10 C11 C12 -.2(3) ?
C15 O C12 C11 -5.8(2) y
C15 O C12 C13 175.51(14) y
C10 C11 C12 O -178.95(16) ?
C10 C11 C12 C13 -.3(3) ?
O C12 C13 C14 179.23(15) ?
C11 C12 C13 C14 .4(3) ?
C12 C13 C14 C9 -.2(3) ?
C10 C9 C14 C13 -.2(2) ?
C8 C9 C14 C13 179.66(15) ?
C22 B C16 C17 -123.47(15) ?
C28 B C16 C17 116.71(15) ?
C34 B C16 C17 -5.28(19) ?
C22 B C16 C21 59.85(17) ?
C28 B C16 C21 -59.97(17) ?
C34 B C16 C21 178.03(13) ?
C21 C16 C17 C18 .5(2) ?
B C16 C17 C18 -176.39(15) ?
C16 C17 C18 C19 -1.2(3) ?
C17 C18 C19 C20 .4(3) ?
C18 C19 C20 C21 .9(2) ?
C19 C20 C21 C16 -1.6(2) ?
C17 C16 C21 C20 .9(2) ?
B C16 C21 C20 177.89(13) ?
C28 B C22 C23 109.35(16) ?
C34 B C22 C23 -128.17(15) ?
C16 B C22 C23 -7.7(2) ?
C28 B C22 C27 -70.63(17) ?
C34 B C22 C27 51.85(17) ?
C16 B C22 C27 172.32(13) ?
C27 C22 C23 C24 -.4(2) ?
B C22 C23 C24 179.64(15) ?
C22 C23 C24 C25 .3(3) ?
C23 C24 C25 C26 .0(3) ?
C24 C25 C26 C27 -.2(3) ?
C25 C26 C27 C22 .1(3) ?
C23 C22 C27 C26 .2(2) ?
B C22 C27 C26 -179.80(16) ?
C22 B C28 C29 -9.31(19) ?
C34 B C28 C29 -127.49(15) ?
C16 B C28 C29 112.57(15) ?
C22 B C28 C33 175.26(12) ?
C34 B C28 C33 57.09(17) ?
C16 B C28 C33 -62.85(16) ?
C33 C28 C29 C30 -1.0(2) ?
B C28 C29 C30 -176.67(13) ?
C28 C29 C30 C31 -.9(2) ?
C29 C30 C31 C32 1.5(2) ?
C30 C31 C32 C33 -.1(2) ?
C31 C32 C33 C28 -1.9(2) ?
C29 C28 C33 C32 2.4(2) ?
B C28 C33 C32 178.20(13) ?
C22 B C34 C39 50.68(16) ?
C28 B C34 C39 171.10(13) ?
C16 B C34 C39 -71.76(16) ?
C22 B C34 C35 -128.85(14) ?
C28 B C34 C35 -8.4(2) ?
C16 B C34 C35 108.71(16) ?
C39 C34 C35 C36 1.1(2) ?
B C34 C35 C36 -179.30(14) ?
C34 C35 C36 C37 -1.8(2) ?
C35 C36 C37 C38 .7(2) ?
C36 C37 C38 C39 .8(2) ?
C37 C38 C39 C34 -1.5(2) ?
C35 C34 C39 C38 .5(2) ?
B C34 C39 C38 -179.12(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652302
