#------------------------------------------------------------------------------
#$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: svn://www.crystallography.net/cod/cif/2/2200388.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2200388
loop_
_publ_author_name
'Camiolo, Salvatore'
'Coles, Simon J.'
'Gale, Philip A.'
'Hursthouse, Michael B.'
'Sessler, Jonathan L.'
_publ_section_title
;
Tetrabutylammonium  meso-octamethylcalix[4]pyrrole fluoride dichloromethane
solvate
;
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o816
_journal_page_last               o818
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C16 H36 N 1+, C28 H36 N4, F 1-, C H2 Cl2'
_chemical_formula_moiety         'C16 H36 N 1+, C28 H36 N4, F 1-, C H2 Cl2'
_chemical_formula_sum            'C45 H64 Cl2 F N5'
_chemical_formula_weight         764.91
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P m n 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   19.846(4)
_cell_length_b                   10.653(2)
_cell_length_c                   10.469(2)
_cell_measurement_temperature    100(2)
_cell_volume                     2213.3(8)
_exptl_crystal_density_diffrn    1.148
_cod_depositor_comments
;
The following automatic conversions were performed:
'_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               2200388
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y, z+1/2'
'-x, y, z'
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
C23 .5 .6387(14) .9583(10) .124(5) Uani d S 1 . . C
H23A .5 .7081 .8954 .148 Uiso calc SR 1 . . H
H23B .5 .559 .9097 .148 Uiso calc SR 1 . . H
Cl1 .4255(2) .6468(3) 1.0462(3) .1823(19) Uani d U 1 . . Cl
C1 .35361(17) .0451(3) .6689(4) .0314(7) Uani d . 1 . . C
C2 .30480(18) .0584(4) .5779(4) .0389(9) Uani d . 1 . . C
H2 .2763 -.0063 .5465 .047 Uiso calc R 1 . . H
C3 .3042(2) .1854(4) .5385(4) .0420(9) Uani d . 1 . . C
H3 .2748 .2214 .4769 .05 Uiso calc R 1 . . H
C4 .35389(19) .2475(3) .6053(4) .0337(8) Uani d . 1 . . C
C5 .37307(18) -.0667(3) .7510(4) .0312(8) Uani d . 1 . . C
C6 .3705(2) -.0278(4) .8931(4) .0413(9) Uani d . 1 . . C
H6A .4041 .0377 .9092 .062 Uiso calc R 1 . . H
H6B .3803 -.1009 .9469 .062 Uiso calc R 1 . . H
H6C .3255 .0044 .9135 .062 Uiso calc R 1 . . H
C7 .32212(19) -.1737(4) .7299(5) .0449(10) Uani d . 1 . . C
H7A .2765 -.1429 .7469 .067 Uiso calc R 1 . . H
H7B .3324 -.2432 .788 .067 Uiso calc R 1 . . H
H7C .325 -.2031 .6413 .067 Uiso calc R 1 . . H
C8 .44301(17) -.1155(3) .7193(3) .0260(7) Uani d . 1 . . C
C9 .46408(16) -.2248(3) .6618(3) .0260(7) Uani d . 1 . . C
H9 .4358 -.2888 .6281 .031 Uiso calc R 1 . . H
C10 .3733(2) .3863(4) .6102(4) .0401(9) Uani d . 1 . . C
C11 .3697(3) .4327(4) .7504(4) .0463(10) Uani d . 1 . . C
H11A .4017 .385 .8026 .069 Uiso calc R 1 . . H
H11B .324 .4204 .7834 .069 Uiso calc R 1 . . H
H11C .3812 .5222 .7538 .069 Uiso calc R 1 . . H
C12 .3210(3) .4598(5) .5309(6) .0608(14) Uani d . 1 . . C
H12A .3289 .5501 .5408 .091 Uiso calc R 1 . . H
H12B .2756 .4392 .5607 .091 Uiso calc R 1 . . H
H12C .3254 .4368 .4406 .091 Uiso calc R 1 . . H
C13 .4429(2) .4112(3) .5585(4) .0379(9) Uani d . 1 . . C
C14 .4645(2) .4790(4) .4531(4) .0436(9) Uani d . 1 . . C
H14 .4364 .5185 .3917 .052 Uiso calc R 1 . . H
N1 .38363(14) .1611(3) .6846(3) .0302(6) Uani d . 1 . . N
H1 .4169 .1772 .7376 .036 Uiso calc R 1 . . H
N2 .5 -.0491(3) .7543(4) .0244(8) Uani d S 1 . . N
H2A .5 .0243 .7929 .029 Uiso calc SR 1 . . H
N3 .5 .3712(4) .6214(4) .0326(9) Uani d S 1 . . N
H3A .5 .3264 .692 .039 Uiso calc SR 1 . . H
F1 .5 .2000(2) .8234(3) .0289(6) Uani d S 1 . . F
N4 .5 .0539(4) .2866(4) .0239(8) Uani d S 1 . 2 N
C15 .4582(3) -.0020(6) .3947(6) .0139(12) Uani d P .4 . 1 C
H15A .4444 .012 .4844 .017 Uiso calc PR .4 . 1 H
H15B .4444 .0739 .3468 .017 Uiso calc PR .4 . 1 H
C16 .4110(2) -.1152(4) .3420(7) .0603(16) Uani d P .5 A 1 C
H16A .4387 -.1595 .2776 .072 Uiso calc PR .5 A 1 H
H16B .4062 -.174 .4146 .072 Uiso calc PR .5 A 1 H
C17 .3488(4) -.1065(8) .2898(8) .0422(16) Uani d P .6 A 1 C
H17A .3534 -.0992 .1959 .051 Uiso calc PR .6 A 1 H
H17B .3269 -.0289 .3212 .051 Uiso calc PR .6 A 1 H
C18 .3001(2) -.2269(5) .3229(5) .0505(11) Uani d P .5 A 1 C
H18A .3217 -.3043 .2933 .076 Uiso calc PR .5 A 1 H
H18B .2567 -.2166 .2796 .076 Uiso calc PR .5 A 1 H
H18C .2929 -.2315 .4153 .076 Uiso calc PR .5 A 1 H
C19 .4566(3) .1044(6) .1796(6) .0148(12) Uani d P .4 . 1 C
H19A .4435 .091 .0894 .018 Uiso calc PR .4 . 1 H
H19B .4435 .0271 .2257 .018 Uiso calc PR .4 . 1 H
C20 .4060(3) .2131(5) .2323(11) .091(3) Uani d P .5 B 1 C
H20A .3742 .1802 .297 .11 Uiso calc PR .5 B 1 H
H20B .431 .2854 .2681 .11 Uiso calc PR .5 B 1 H
C21 .3684(4) .2486(9) .1004(9) .0516(18) Uani d P .6 B 1 C
H21A .402 .2615 .0317 .062 Uiso calc PR .6 B 1 H
H21B .3381 .1794 .0744 .062 Uiso calc PR .6 B 1 H
C22 .3317(3) .3574(6) .1192(6) .0696(15) Uani d P .5 B 1 C
H22A .2961 .3417 .1821 .104 Uiso calc PR .5 B 1 H
H22B .3113 .3838 .0383 .104 Uiso calc PR .5 B 1 H
H22C .3615 .4238 .1507 .104 Uiso calc PR .5 B 1 H
C15' .4551(4) -.0459(7) .2263(7) .0414(15) Uani d P .6 C 2 C
H15C .483 -.1088 .181 .05 Uiso calc PR .6 C 2 H
H15D .4242 -.0068 .1637 .05 Uiso calc PR .6 C 2 H
C16' .4110(2) -.1152(4) .3420(7) .0603(16) Uani d P .5 C 2 C
C17' .3463(6) -.1661(13) .2460(12) .048(3) Uani d P .4 C 2 C
H17C .3248 -.0938 .2027 .058 Uiso calc PR .4 C 2 H
H17D .3637 -.2242 .18 .058 Uiso calc PR .4 C 2 H
C18' .3001(2) -.2269(5) .3229(5) .0505(11) Uani d P .5 C 2 C
C19' .4577(3) .1589(6) .3477(7) .0384(14) Uani d P .6 D 2 C
H19C .4872 .227 .3795 .046 Uiso calc PR .6 D 2 H
H19D .4311 .1256 .4203 .046 Uiso calc PR .6 D 2 H
C20' .4060(3) .2131(5) .2323(11) .091(3) Uani d P .5 D 2 C
C21' .4106(5) .2930(9) .1543(10) .037(2) Uani d P .4 D 2 C
H21C .4306 .2577 .0754 .044 Uiso calc PR .4 D 2 H
H21D .441 .3599 .186 .044 Uiso calc PR .4 D 2 H
C22' .3317(3) .3574(6) .1192(6) .0696(15) Uani d P .5 D 2 C
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
C23 .220(16) .114(9) .037(4) 0 0 -.005(5)
Cl1 .292(5) .142(3) .113(2) -.098(3) .046(3) .031(2)
C1 .0295(15) .0304(16) .0342(17) -.0004(12) .0054(15) -.0083(15)
C2 .0286(15) .043(2) .045(2) .0012(14) -.0004(16) -.0136(17)
C3 .0346(18) .054(2) .037(2) .0096(16) -.0023(16) -.0057(18)
C4 .0383(17) .0340(18) .0288(17) .0059(14) -.0017(15) -.0005(14)
C5 .0306(15) .0274(15) .0355(19) -.0056(13) .0099(14) -.0065(15)
C6 .054(2) .0348(19) .0353(19) -.0041(17) .0201(18) -.0035(16)
C7 .0359(19) .0333(18) .066(3) -.0086(15) .020(2) -.0056(19)
C8 .0324(16) .0214(14) .0243(15) -.0034(12) .0048(13) -.0002(12)
C9 .0338(16) .0206(14) .0237(15) -.0053(12) .0011(13) -.0006(12)
C10 .052(2) .0322(18) .0363(19) .0130(16) -.0041(18) .0042(16)
C11 .066(3) .0252(16) .048(2) .0098(17) .012(2) -.0052(18)
C12 .068(3) .050(3) .064(3) .021(2) -.012(3) .012(2)
C13 .061(2) .0237(15) .0289(17) .0069(15) -.0047(17) .0011(14)
C14 .073(3) .0278(17) .0302(18) .0047(18) -.0076(19) .0036(15)
N1 .0308(13) .0302(14) .0297(13) .0022(11) -.0033(12) -.0019(12)
N2 .0308(18) .0199(16) .0225(18) 0 0 -.0044(14)
N3 .049(2) .0243(18) .0241(19) 0 0 .0011(16)
F1 .0393(14) .0245(12) .0228(13) 0 0 -.0022(11)
N4 .0248(16) .0276(18) .0192(18) 0 0 .0021(15)
C15 .015(3) .018(3) .008(3) .000(2) .004(2) .002(2)
C16 .036(2) .034(2) .111(5) -.0078(16) .025(3) .000(3)
C17 .040(3) .041(4) .045(4) -.004(3) -.005(3) .015(3)
C18 .040(2) .065(3) .046(2) -.0112(19) -.0119(19) .007(2)
C19 .023(3) .012(3) .009(3) -.001(2) -.003(3) .001(2)
C20 .073(4) .038(2) .163(8) .020(2) -.058(5) -.011(4)
C21 .043(4) .063(5) .049(4) .002(3) -.005(4) -.004(4)
C22 .080(4) .076(4) .053(3) .008(3) -.022(3) .014(3)
C15' .050(4) .039(3) .035(3) -.005(3) -.007(3) -.002(3)
C16' .036(2) .034(2) .111(5) -.0078(16) .025(3) .000(3)
C17' .061(7) .049(6) .035(6) -.038(6) -.008(5) .002(5)
C18' .040(2) .065(3) .046(2) -.0112(19) -.0119(19) .007(2)
C19' .042(3) .038(3) .034(3) .002(3) .004(3) -.002(3)
C20' .073(4) .038(2) .163(8) .020(2) -.058(5) -.011(4)
C21' .042(5) .032(5) .035(5) .005(4) -.001(4) .013(4)
C22' .080(4) .076(4) .053(3) .008(3) -.022(3) .014(3)
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
C23 Cl1 . 1.745(7) ?
C23 Cl1 4_655 1.745(7) ?
C23 H23A . .99 ?
C23 H23B . .99 ?
C1 C2 . 1.366(6) ?
C1 N1 . 1.382(5) ?
C1 C5 . 1.518(5) ?
C2 C3 . 1.415(6) ?
C2 H2 . .95 ?
C3 C4 . 1.379(6) ?
C3 H3 . .95 ?
C4 N1 . 1.373(5) ?
C4 C10 . 1.529(5) ?
C5 C8 . 1.519(5) ?
C5 C7 . 1.539(5) ?
C5 C6 . 1.546(6) ?
C6 H6A . .98 ?
C6 H6B . .98 ?
C6 H6C . .98 ?
C7 H7A . .98 ?
C7 H7B . .98 ?
C7 H7C . .98 ?
C8 C9 . 1.376(5) ?
C8 N2 . 1.384(4) ?
C9 C9 4_655 1.426(6) ?
C9 H9 . .95 ?
C10 C13 . 1.508(6) ?
C10 C12 . 1.542(6) ?
C10 C11 . 1.550(6) ?
C11 H11A . .98 ?
C11 H11B . .98 ?
C11 H11C . .98 ?
C12 H12A . .98 ?
C12 H12B . .98 ?
C12 H12C . .98 ?
C13 N3 . 1.378(5) ?
C13 C14 . 1.387(6) ?
C14 C14 4_655 1.408(10) ?
C14 H14 . .95 ?
N1 H1 . .88 ?
N2 C8 4_655 1.384(4) ?
N2 H2A . .88 ?
N3 C13 4_655 1.378(5) ?
N3 H3A . .88 ?
N4 C15' . 1.525(7) ?
N4 C15' 4_655 1.525(7) ?
N4 C19' 4_655 1.538(7) ?
N4 C19' . 1.538(7) ?
C15 C16 . 1.623(8) ?
C15 C15 4_655 1.660(12) ?
C15 H15A . .99 ?
C15 H15B . .99 ?
C16 C17 . 1.353(9) ?
C16 H16A . .99 ?
C16 H16B . .99 ?
C17 C18 . 1.643(9) ?
C17 H17A . .99 ?
C17 H17B . .99 ?
C18 H18A . .98 ?
C18 H18B . .98 ?
C18 H18C . .98 ?
C19 C20 . 1.629(9) ?
C19 C19 4_655 1.722(13) ?
C19 H19A . .99 ?
C19 H19B . .99 ?
C20 C21 . 1.615(12) ?
C20 H20A . .99 ?
C20 H20B . .99 ?
C21 C22 . 1.384(10) ?
C21 H21A . .99 ?
C21 H21B . .99 ?
C22 H22A . .98 ?
C22 H22B . .98 ?
C22 H22C . .98 ?
C15' H15C . .99 ?
C15' H15D . .99 ?
C17' H17C . .99 ?
C17' H17D . .99 ?
C19' H19C . .99 ?
C19' H19D . .99 ?
C21' H21C . .99 ?
C21' H21D . .99 ?