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#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/13/2101356.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_2101356
loop_
_publ_author_name
'Sheikh-Ali, B. M.'
'Rapta, M.'
'Jameson, G. B.'
'Weiss, R. G.'
_publ_section_title
;
 Molecular conformations and crystal packing properties of five
 4-alkyl-N-(4-cyanophenyl)piperidines by X-ray diffraction: a
 surprising dependence upon alkyl chain length
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              823
_journal_page_last               835
_journal_paper_doi               10.1107/S0108768194013054
_journal_volume                  51
_journal_year                    1995
_chemical_formula_sum            'C20 H30 N2'
_chemical_formula_weight         298.52
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.0
_cell_angle_beta                 102.74(3)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   12.331(2)
_cell_length_b                   11.086(2)
_cell_length_c                   13.929(3)
_cell_volume                     1857.2(6)
_diffrn_radiation_type           Cu
_diffrn_radiation_wavelength     1.54184
_exptl_absorpt_coefficient_mu    0.438
_exptl_crystal_density_diffrn    1.067
_exptl_crystal_F_000             656
_cod_data_source_file            gr0375.cif
_cod_data_source_block           gr0375e
_cod_database_code               2101356
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
N(1) -.0150(4) .1499(4) .0138(4) .083(2)
C(2) .0184(4) .1227(4) .0947(4) .063(2)
C(3) .0592(4) .0915(4) .1950(3) .0500(10)
C(4) .0660(4) .1770(4) .2686(4) .0550(10)
C(5) .1027(4) .1492(4) .3658(3) .0540(10)
C(6) .1359(4) .0317(4) .3965(3) .0470(10)
C(7) .1296(4) -.0544(4) .3209(3) .0530(10)
C(8) .0923(4) -.0256(4) .2233(3) .0550(10)
N(9) .1719(3) .0019(3) .4945(3) .0540(10)
C(10) .1845(5) .0968(4) .5682(3) .064(2)
C(12) .2485(6) -.0532(5) .7039(3) .090(2)
C(13) .2286(5) -.1492(4) .6269(3) .064(2)
C(11A) .2382(9) .0659(9) .6657(7) .056(2)
C(14A) .1712(10) -.1171(9) .5231(7) .060(2)
C(11B) .1812(10) .0498(9) .6746(7) .056(2)
C(14B) .2426(10) -.1069(9) .5269(7) .060(2)
C(15) .2720(4) -.0930(4) .8068(3) .061(2)
C(16) .2891(5) .0000(5) .8870(3) .067(2)
C(17) .3227(4) -.0464(4) .9907(3) .062(2)
C(18) .3386(5) .0503(5) 1.0687(3) .066(2)
C(19) .3779(4) .0071(4) 1.1735(3) .059(2)
C(20) .3910(4) .1056(4) 1.2496(3) .059(2)
C(21) .4273(4) .0641(5) 1.3553(3) .065(2)
C(22) .4380(5) .1650(5) 1.4284(4) .083(2)
H(4A) .0382(4) .2571(4) .2524(4) .066
H(5A) .1233(4) .2132(4) .4127(3) .064
H(7A) .1594(4) -.1331(4) .3396(3) .064
H(8A) .0885(4) -.0868(4) .1739(3) .066
H(10C) .1271(5) .1556(4) .5470(3) .080
H(10D) .2547(5) .1362(4) .5723(3) .080
H(10A) .1116(5) .1262(4) .5696(3) .080
H(10B) .2247(5) .1623(4) .5472(3) .080
H(12B) .3194(6) -.0218(5) .6984(3) .080
H(12A) .1704(6) -.0534(5) .7029(3) .080
H(13C) .1553(5) -.1825(4) .6191(3) .080
H(13D) .2808(5) -.2127(4) .6498(3) .080
H(13A) .1883(5) -.2144(4) .6481(3) .080
H(13B) .3010(5) -.1795(4) .6249(3) .080
H(11A) .2047(9) .1142(9) .7085(7) .067
H(11B) .3135(9) .0936(9) .6743(7) .067
H(14A) .2042(10) -.1641(9) .4792(7) .072
H(14B) .0952(10) -.1425(9) .5139(7) .072
H(11C) .1054(10) .0308(9) .6753(7) .067
H(11D) .2051(10) .1132(9) .7214(7) .067
H(14C) .3190(10) -.0862(9) .5308(7) .072
H(14D) .2226(10) -.1706(9) .4797(7) .072
H(15A) .3404(4) -.1375(4) .8188(3) .073
H(15B) .2146(4) -.1482(4) .8147(3) .073
H(16A) .3384(5) .0623(5) .8747(3) .080
H(16B) .2175(5) .0358(5) .8834(3) .080
H(17A) .2724(4) -.1065(4) 1.0049(3) .075
H(17B) .3939(4) -.0836(4) .9949(3) .075
H(18A) .2687(5) .0910(5) 1.0623(3) .079
H(18B) .3930(5) .1078(5) 1.0580(3) .079
H(19A) .4490(4) -.0314(4) 1.1810(3) .071
H(19B) .3247(4) -.0519(4) 1.1839(3) .071
H(20A) .3180(4) .1371(4) 1.2476(3) .071
H(20B) .4363(4) .1695(4) 1.2331(3) .071
H(21A) .5021(4) .0374(5) 1.3587(3) .078
H(21B) .3846(4) -.0028(5) 1.3705(3) .078
H(22A) .4686(5) .1350(5) 1.4934(4) .125
H(22B) .4831(5) .2301(5) 1.4139(4) .125
H(22C) .3637(5) .1934(5) 1.4249(4) .125
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N(1) C(2) C(3) 178.9(6)
C(4) C(3) C(8) 117.6(4)
C(4) C(3) C(2) 120.8(4)
C(8) C(3) C(2) 121.6(4)
C(5) C(4) C(3) 122.2(4)
C(4) C(5) C(6) 121.5(4)
N(9) C(6) C(5) 122.2(4)
N(9) C(6) C(7) 121.9(4)
C(5) C(6) C(7) 115.9(4)
C(8) C(7) C(6) 122.2(4)
C(7) C(8) C(3) 120.7(4)
C(14A) N(9) C(6) 119.6(5)
C(14A) N(9) C(10) 119.7(5)
C(6) N(9) C(10) 119.1(4)
C(14A) N(9) C(14B) 35.2(5)
C(6) N(9) C(14B) 122.0(5)
C(10) N(9) C(14B) 113.9(5)
C(11A) C(10) N(9) 117.2(5)
C(11A) C(10) C(11B) 28.8(6)
N(9) C(10) C(11B) 113.7(5)
C(11B) C(12) C(11A) 31.1(6)
C(11B) C(12) C(15) 120.0(6)
C(11A) C(12) C(15) 128.9(6)
C(11B) C(12) C(13) 112.0(6)
C(11A) C(12) C(13) 114.1(5)
C(15) C(12) C(13) 117.0(6)
C(12) C(13) C(14A) 119.3(5)
C(12) C(13) C(14B) 113.9(5)
C(14A) C(13) C(14B) 33.8(5)
C(11B) C(11A) C(10) 87.7(13)
C(11B) C(11A) C(12) 74.3(12)
C(10) C(11A) C(12) 124.6(8)
C(14B) C(14A) N(9) 79.8(11)
(14B) C(14A) C(13) 73.7(10)
N(9) C(14A) C(13) 118.2(7)
C(11A) C(11B) C(12) 74.5(12)
C(11A) C(11B) C(10) 63.5(11)
C(12) C(11B) C(10) 113.6(7)
C(14A) C(14B) N(9) 64.9(10)
C(14A) C(14B) C(13) 72.5(10)
N(9) C(14B) C(13) 110.5(7)
C(12) C(15) C(16) 119.1(4)
(15) C(16) C(17) 116.4(4)
C(16) C(17) C(18) 114.5(4)
C(17) C(18) C(19) 115.7(4)
C(20) C(19) C(18) 114.3(4)
C(19) C(20) C(21) 115.3(4)
C(22) C(21) C(20) 113.4(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N(1) C(2) 1.151(6)
C(2) C(3) 1.420(7)
C(3) C(4) 1.384(6)
C(3) C(8) 1.392(6)
C(4) C(5) 1.365(6)
C(5) C(6) 1.404(6)
C(6) N(9) 1.379(5)
C(6) C(7) 1.411(6)
C(7) C(8) 1.373(6)
N(9) C(14A) 1.379(10)
N(9) C(10) 1.454(6)
N(9) C(14B) 1.498(11)
C(10) C(11A) 1.415(10)
C(10) C(11B) 1.580(10)
C(12) C(11B) 1.418(11)
C(12) C(11A) 1.419(11)
C(12) C(15) 1.467(6)
C(12) C(13) 1.492(7)
C(13) C(14A) 1.505(10)
C(13) C(14B) 1.515(10)
C(11A) C(11B) 0.761(14)
C(14A) C(14B) 0.877(13)
C(15) C(16) 1.499(6)
C(16) C(17) 1.503(6)
C(17) C(18) 1.508(6)
C(18) C(19) 1.511(6)
C(19) C(20) 1.505(6)
C(20) C(21) 1.514(6)
C(21) C(22) 1.498(7)
