#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/10/2001057.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_2001057
loop_
_publ_author_name
'Kanters, J. A.'
'ter Horst, E. H.'
'Kroon, J.'
'Grech, E.'
_publ_section_title
;
 Complexes of the `proton sponge' 1,8-bis(dimethylamino)naphthalene
 (DMAN). III. Structure of
 [DMANH]⁺.[pentachlorophenolate]^{-^}.[pentachlorophenol]₂ at 100 K
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              328
_journal_page_last               332
_journal_paper_doi               10.1107/S0108270191009459
_journal_volume                  48
_journal_year                    1992
_chemical_formula_moiety         'C14 H19 N2,2(C6 H1 Cl5 O1),C6 Cl5 O1'
_chemical_formula_sum            'C32 H21 Cl15 N2 O3'
_chemical_formula_weight         1013.3
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.363(2)
_cell_length_b                   16.676(2)
_cell_length_c                   20.307(2)
_cell_volume                     3848.0(9)
_diffrn_radiation_type           Mo
_diffrn_radiation_wavelength     0.71073
_exptl_absorpt_coefficient_mu    1.12
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_F_000             2024
_cod_data_source_file            ge0273.cif
_cod_data_source_block           ge0273a
_cod_original_cell_volume        3847.9(4)
_cod_database_code               2001057
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
N(1) .03384(18) .02774(13) .33387(10) .0121(6)
H(1) -.034(2) -.0202(16) .3373(13) .0239(17)
N(2) -.11475(18) -.08122(13) .36407(10) .0135(7)
C(1) .0438(2) .04964(15) .40401(12) .0137(7)
C(2) .1065(2) .11515(17) .42346(13) .0180(8)
C(3) .1193(2) .13203(18) .49090(14) .0206(9)
C(4) .0736(2) .08134(17) .53678(13) .0200(9)
C(5) -.0365(2) -.04079(17) .56593(13) .0186(8)
C(6) -.0978(2) -.10742(18) .54802(13) .0197(8)
C(7) -.1215(2) -.12209(16) .48102(13) .0165(8)
C(8) -.0812(2) -.07089(16) .43349(12) .0135(7)
C(9) -.0107(2) -.00338(15) .44977(12) .0125(8)
C(10) .0091(2) .01249(15) .51819(13) .0145(8)
C(11) -.0046(2) .09392(17) .29072(14) .0180(8)
C(12) .1432(3) -.01052(18) .30907(14) .0221(9)
C(13) -.0874(3) -.16170(17) .33781(14) .0197(9)
C(14) -.2399(2) -.05945(19) .35412(14) .0202(9)
O(1) .80086(14) .23628(10) .24335(8) .0141(5)
C(15) .6879(2) .23191(14) .25142(11) .0112(7)
C(16) .6189(2) .29694(14) .27387(11) .0115(7)
C(17) .4977(2) .29378(15) .27991(11) .0115(7)
C(18) .43773(19) .22315(15) .26561(11) .0114(7)
C(19) .5021(2) .15618(15) .24649(12) .0123(7)
C(20) .6230(2) .16110(14) .23859(11) .0115(7)
Cl(1) .69337(5) .38435(4) .29397(3) .0172(2)
Cl(2) .41905(5) .37766(4) .30361(3) .0171(2)
Cl(3) .28591(5) .21900(4) .27157(3) .0194(2)
Cl(4) .43075(5) .06582(4) .23492(3) .0187(2)
Cl(5) .70282(5) .07847(4) .21261(3) .0159(2)
O(2) .95446(16) .16925(11) .16125(9) .0159(6)
H(8) .896(2) .1905(17) .1738(14) .0239(17)
C(21) .9695(2) .16582(15) .09597(12) .0135(7)
C(22) .9067(2) .21165(16) .05040(13) .0155(8)
C(23) .9311(2) .20612(16) -.01692(13) .0181(8)
C(24) 1.0151(2) .15269(17) -.03959(12) .0186(8)
C(25) 1.0783(2) .10691(16) .00529(13) .0176(8)
C(26) 1.0578(2) .11481(15) .07222(12) .0153(7)
Cl(6) .80033(6) .27591(4) .07961(3) .0211(2)
Cl(7) .85622(6) .26736(4) -.07149(3) .0257(2)
Cl(8) 1.04208(6) .14388(5) -.12306(3) .0305(2)
Cl(9) 1.18137(6) .03852(4) -.02197(3) .0253(2)
Cl(10) 1.14147(6) .06238(4) .12842(3) .0231(2)
O(3) -.04133(16) .30593(11) .31216(9) .0171(6)
H(9) -.102(2) .2851(17) .2996(14) .0239(17)
C(27) -.0310(2) .32121(15) .37615(12) .0144(8)
C(28) .0501(2) .38059(15) .39502(12) .0145(8)
C(29) .0711(2) .39876(15) .46060(13) .0160(8)
C(30) .0114(2) .35788(17) .51005(13) .0179(8)
C(31) -.0694(2) .29887(15) .49293(12) .0142(8)
C(32) -.0920(2) .28167(16) .42700(12) .0142(7)
Cl(11) .12259(6) .43158(4) .33323(3) .0202(2)
Cl(12) .17220(6) .47200(4) .48044(3) .0245(2)
Cl(13) .03438(6) .38161(5) .59174(3) .0253(2)
Cl(14) -.13929(6) .24470(4) .55370(3) .0219(2)
Cl(15) -.19613(6) .21097(4) .40589(3) .0193(2)
H(2) .144(2) .1484(16) .3934(12) ?
H(3) .160(2) .1758(16) .5049(12) ?
H(4) .083(2) .0949(15) .5823(13) ?
H(5) -.020(2) -.0272(16) .6119(13) ?
H(6) -.127(2) -.1437(16) .5814(12) ?
H(7) -.165(2) -.1704(15) .4674(12) ?
H(111) -.077(2) .1164(16) .3060(13) ?
H(112) -.016(2) .0720(16) .2470(13) ?
H(113) .056(2) .1336(16) .2888(12) ?
H(121) .206(2) .0284(16) .3063(13) ?
H(122) .170(2) -.0557(17) .3390(12) ?
H(123) .127(2) -.0339(16) .2653(13) ?
H(131) -.140(2) -.2028(16) .3576(13) ?
H(132) -.112(2) -.1613(16) .2922(14) ?
H(133) .002(2) -.1704(16) .3462(13) ?
H(141) -.255(2) -.0001(17) .3683(13) ?
H(142) -.300(2) -.0968(15) .3758(12) ?
H(143) -.258(2) -.0614(16) .3075(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N(1) H(1) 1.11(2)
N(1) C(11) 1.475(4)
N(2) C(8) 1.470(3)
N(2) C(14) 1.482(3)
C(1) C(9) 1.424(3)
C(3) C(4) 1.361(4)
C(5) C(6) 1.361(4)
C(6) C(7) 1.408(4)
C(8) C(9) 1.421(4)
N(1) C(1) 1.475(3)
N(1) C(12) 1.485(4)
N(2) C(13) 1.477(4)
C(1) C(2) 1.363(4)
C(2) C(3) 1.406(4)
C(4) C(10) 1.413(4)
C(5) C(10) 1.413(4)
C(7) C(8) 1.368(4)
C(9) C(10) 1.432(4)
O(1) C(15) 1.296(3)
C(15) C(20) 1.416(3)
C(17) C(18) 1.391(3)
C(19) C(20) 1.386(3)
Cl(2) C(17) 1.728(3)
Cl(4) C(19) 1.727(3)
C(15) C(16) 1.414(3)
C(16) C(17) 1.384(3)
C(18) C(19) 1.390(3)
Cl(1) C(16) 1.734(2)
Cl(3) C(18) 1.731(2)
Cl(5) C(20) 1.732(2)
O(2) H(8) 0.79(2)
C(21) C(22) 1.396(4)
C(22) C(23) 1.398(4)
C(24) C(25) 1.389(4)
Cl(6) C(22) 1.721(3)
Cl(8) C(24) 1.729(3)
Cl(10) C(26) 1.724(2)
O(2) C(21) 1.338(3)
C(21) C(26) 1.401(3)
C(23) C(24) 1.384(4)
C(25) C(26) 1.385(4)
Cl(7) C(23) 1.731(3)
Cl(9) C(25) 1.726(3)
O(3) H(9) 0.81(2)
C(27) C(28) 1.406(3)
C(28) C(29) 1.386(4)
C(30) C(31) 1.390(4)
Cl(11) C(28) 1.725(3)
Cl(13) C(30) 1.725(3)
Cl(15) C(32) 1.724(3)
O(3) C(27) 1.329(3)
C(27) C(32) 1.408(3)
C(29) C(30) 1.390(4)
C(31) C(32) 1.393(3)
Cl(12) C(29) 1.724(3)
Cl(14) C(31) 1.723(3)
