#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2101189.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_2101189
loop_
_publ_author_name
'Jones, R.'
'Scheffer, J. R.'
'Trotter, J.'
'Yang, J.'
_publ_section_title
;
Crystal structures, chiralities and photochemistry of two polymorphs
of L-prolinolium
\a-adamantylacetophenone-p-carboxylate
;
_journal_issue 5
_journal_name_full 'Acta Crystallographica Section B'
_journal_page_first 601
_journal_page_last 607
_journal_volume 50
_journal_year 1994
_chemical_formula_sum 'C24 H33 N O4'
_chemical_formula_weight 399.53
_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 8
_cell_length_a 11.7980(10)
_cell_length_b 43.563(3)
_cell_length_c 8.4434(8)
_cell_volume 4339.5(6)
_diffrn_radiation_type Cu
_diffrn_radiation_wavelength 1.54178
_exptl_absorpt_coefficient_mu 0.62
_exptl_crystal_density_diffrn 1.22
_exptl_crystal_F_000 1728
_[local]_cod_data_source_file br0026.cif
_[local]_cod_data_source_block br0026b
_[local]_cod_chemical_formula_sum_orig 'C24 H33 N1 O4'
_cod_original_cell_volume 4340.0(10)
_cod_database_code 2101189
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
O(12) .8716(4) .40320(10) .1354(5)
O(19) 1.2797(4) .29760(10) .4862(5)
O(20) 1.2243(3) .27790(9) .2640(4)
O(26) 1.4635(4) .26091(8) .5211(5)
O(42) .3703(4) .40510(10) .3921(5)
O(49) .7712(4) .29877(9) .0311(5)
O(50) .6900(3) .27448(8) .2403(4)
O(56) .9536(4) .26376(8) .0143(6)
N(21) 1.2544(4) .22390(10) .4408(5)
N(51) .7445(4) .22250(10) .0742(5)
C(1) .8632(5) .43870(10) .4701(7)
C(2) .7398(5) .44090(10) .4058(8)
C(3) .6593(5) .4461(2) .5438(8)
C(4) .6622(5) .4201(2) .6585(8)
C(5) .7803(6) .4184(2) .7238(7)
C(6) .8114(7) .4467(2) .8076(8)
C(7) .8062(6) .47340(10) .6917(8)
C(8) .8921(6) .46740(10) .5551(8)
C(9) .8658(6) .41160(10) .5889(8)
C(10) .6878(6) .47510(10) .6246(8)
C(11) .9501(5) .43440(10) .3327(8)
C(12) .9392(5) .40460(10) .2438(7)
C(13) 1.0118(4) .37740(10) .2824(6)
C(14) 1.1020(4) .37930(10) .3861(7)
C(15) 1.1682(4) .35260(10) .4151(7)
C(16) 1.1469(4) .32620(10) .3370(6)
C(17) 1.0588(5) .32360(10) .2331(6)
C(18) .9887(4) .34880(10) .2075(6)
C(19) 1.2203(5) .29750(10) .3631(7)
C(20) 1.3716(4) .21140(10) .4694(7)
C(22) 1.1938(5) .1997(2) .3443(7)
C(23) 1.2611(6) .17040(10) .3675(8)
C(24) 1.3778(5) .18170(10) .3721(8)
C(25) 1.4591(6) .23390(10) .4244(7)
C(31) .3590(5) .43890(10) .0500(6)
C(32) .2411(5) .44040(10) .1156(7)
C(33) .1540(5) .4461(2) -.0155(8)
C(34) .1658(6) .4194(2) -.1336(9)
C(35) .2832(6) .41740(10) -.2014(8)
C(36) .3083(6) .4484(2) -.2884(7)
C(37) .2990(6) .47470(10) -.1713(8)
C(38) .3817(5) .47010(10) -.0384(8)
C(39) .3664(5) .41320(10) -.0699(7)
C(40) .1801(6) .4774(2) -.1004(8)
C(41) .4467(5) .43570(10) .1834(8)
C(42) .4381(5) .40680(10) .2834(7)
C(43) .5087(4) .37940(10) .2434(6)
C(44) .5954(5) .37920(10) .1321(7)
C(45) .6597(5) .35410(10) .1038(7)
C(46) .6371(5) .32630(10) .1819(6)
C(47) .5471(5) .32640(10) .2903(6)
C(48) .4872(5) .35280(10) .3233(7)
C(49) .7074(5) .29860(10) .1483(7)
C(50) .8676(5) .21650(10) .1161(6)
C(52) .6782(5) .19780(10) .1432(7)
C(53) .7494(6) .17030(10) .1125(9)
C(54) .8716(6) .1823(2) .1140(10)
C(55) .9508(5) .23230(10) .0044(7)
H(2A) .7340 .4573 .3326
H(2B) .7204 .4221 .3539
H(3) .5844 .4478 .5020
H(4A) .6096 .4238 .7414
H(4B) .6438 .4015 .6063
H(5) .7830 .4020 .7974
H(6A) .7600 .4502 .8927
H(6B) .8862 .4449 .8490
H(7) .8240 .4920 .7438
H(8A) .8909 .4841 .4829
H(8B) .9667 .4655 .5985
H(9A) .8445 .3932 .5370
H(9B) .9395 .4094 .6323
H(10A) .6833 .4915 .5514
H(10B) .6354 .4783 .7083
H(11A) .9398 .4508 .2594
H(11B) 1.0242 .4354 .3760
H(14) 1.1191 .3981 .4376
H(15) 1.2283 .3534 .4902
H(17) 1.0454 .3050 .1793
H(18) .9247 .3468 .1396
H(20) 1.3784 .2067 .5782
H(21A) 1.2575 .2427 .3825
H(21B) 1.2156 .2273 .5376
H(22A) 1.1178 .1972 .3812
H(22B) 1.1921 .2052 .2354
H(23A) 1.2406 .1606 .4648
H(23B) 1.2494 .1565 .2828
H(24A) 1.4048 .1856 .2684
H(24B) 1.4262 .1672 .4228
H(25A) 1.4469 .2402 .3184
H(25B) 1.5313 .2242 .4326
H(26) 1.3919 .2716 .5148
H(32A) .2371 .4569 .1899
H(32B) .2240 .4217 .1671
H(33) .0797 .4465 .0272
H(34A) .1132 .4220 -.2172
H(34B) .1493 .4006 -.0793
H(35) .2884 .4006 -.2736
H(36A) .2544 .4511 -.3710
H(36B) .3823 .4477 -.3319
H(37) .3173 .4933 -.2251
H(38A) .3735 .4866 .0352
H(38B) .4564 .4701 -.0793
H(39A) .3516 .3943 -.0175
H(39B) .4410 .4129 -.1126
H(40A) .1264 .4813 -.1817
H(40B) .1784 .4938 -.0258
H(41A) .4387 .4528 .2517
H(41B) .5199 .4362 .1363
H(44) .6107 .3974 .0735
H(45) .7206 .3552 .0306
H(47) .5266 .3078 .3426
H(48) .4305 .3525 .4028
H(50) .8821 .2236 .2209
H(51A) .7213 .2420 .1145
H(51B) .7359 .2229 -.0391
H(52A) .6690 .2009 .2540
H(52B) .6070 .1959 .0940
H(53A) .7390 .1554 .1937
H(53B) .7317 .1616 .0130
H(54A) .9101 .1754 .0220
H(54B) .9097 .1750 .2057
H(55A) .9293 .2271 -.1016
H(55B) 1.0243 .2248 .0248
H(56) .8802 .2718 -.0087
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(20) N(21) C(22) 105.6(4)
C(50) N(51) C(52) 107.0(4)
C(2) C(1) C(8) 109.5(5)
C(2) C(1) C(9) 106.9(5)
C(2) C(1) C(11) 111.2(5)
C(8) C(1) C(9) 109.0(5)
C(8) C(1) C(11) 108.1(5)
C(9) C(1) C(11) 112.1(4)
C(1) C(2) C(3) 109.0(5)
C(2) C(3) C(4) 111.7(5)
C(2) C(3) C(10) 109.8(5)
C(4) C(3) C(10) 110.2(6)
C(3) C(4) C(5) 107.3(5)
C(4) C(5) C(6) 111.5(6)
C(4) C(5) C(9) 110.1(5)
C(6) C(5) C(9) 110.5(6)
C(5) C(6) C(7) 108.9(6)
C(6) C(7) C(8) 108.8(5)
C(6) C(7) C(10) 108.3(6)
C(8) C(7) C(10) 109.4(6)
C(1) C(8) C(7) 110.5(5)
C(1) C(9) C(5) 108.5(5)
C(3) C(10) C(7) 110.1(5)
C(1) C(11) C(12) 114.7(5)
O(12) C(12) C(11) 118.5(5)
O(12) C(12) C(13) 119.8(5)
C(11) C(12) C(13) 121.7(5)
C(12) C(13) C(14) 122.0(5)
C(12) C(13) C(18) 119.1(5)
C(14) C(13) C(18) 118.9(5)
C(13) C(14) C(15) 118.8(5)
C(14) C(15) C(16) 120.7(5)
C(15) C(16) C(17) 121.8(5)
C(15) C(16) C(19) 121.2(5)
C(17) C(16) C(19) 117.0(5)
C(16) C(17) C(18) 119.2(5)
C(13) C(18) C(17) 120.5(5)
O(19) C(19) O(20) 124.1(5)
O(19) C(19) C(16) 115.5(5)
O(20) C(19) C(16) 120.2(5)
N(21) C(20) C(24) 105.2(4)
N(21) C(20) C(25) 111.3(4)
C(24) C(20) C(25) 112.9(5)
N(21) C(22) C(23) 105.6(5)
C(22) C(23) C(24) 102.4(4)
C(20) C(24) C(23) 104.6(5)
O(26) C(25) C(20) 115.1(5)
C(32) C(31) C(38) 107.0(4)
C(32) C(31) C(39) 109.5(5)
C(32) C(31) C(41) 111.0(5)
C(38) C(31) C(39) 108.2(4)
C(38) C(31) C(41) 108.1(4)
C(39) C(31) C(41) 112.7(4)
C(31) C(32) C(33) 111.3(5)
C(32) C(33) C(34) 106.6(5)
C(32) C(33) C(40) 109.7(5)
C(34) C(33) C(40) 110.1(5)
C(33) C(34) C(35) 112.0(6)
C(34) C(35) C(36) 107.7(5)
C(34) C(35) C(39) 109.3(6)
C(36) C(35) C(39) 109.2(5)
C(35) C(36) C(37) 109.4(5)
C(36) C(37) C(38) 109.9(5)
C(36) C(37) C(40) 112.4(6)
C(38) C(37) C(40) 108.3(6)
C(31) C(38) C(37) 111.0(5)
C(31) C(39) C(35) 111.8(5)
C(33) C(40) C(37) 106.9(5)
C(31) C(41) C(42) 116.0(5)
O(42) C(42) C(41) 120.9(5)
O(42) C(42) C(43) 119.1(5)
C(41) C(42) C(43) 120.0(5)
C(42) C(43) C(44) 124.5(5)
C(42) C(43) C(48) 117.6(5)
C(44) C(43) C(48) 117.8(5)
C(43) C(44) C(45) 122.5(5)
C(44) C(45) C(46) 120.5(5)
C(45) C(46) C(47) 116.6(5)
C(45) C(46) C(49) 120.2(5)
C(47) C(46) C(49) 123.2(5)
C(46) C(47) C(48) 121.5(5)
C(43) C(48) C(47) 120.9(5)
O(49) C(49) O(50) 124.6(5)
O(49) C(49) C(46) 118.8(5)
O(50) C(49) C(46) 116.4(5)
N(51) C(50) C(54) 101.6(5)
N(51) C(50) C(55) 113.1(4)
C(54) C(50) C(55) 115.2(5)
N(51) C(52) C(53) 102.9(3)
C(52) C(53) C(54) 104.9(5)
C(50) C(54) C(53) 108.0(5)
O(56) C(55) C(50) 115.5(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O(12) C(12) 1.215(8)
O(19) C(19) 1.253(7)
O(20) C(19) 1.197(7)
O(26) C(25) 1.435(7)
O(42) C(42) 1.220(8)
O(49) C(49) 1.243(7)
O(50) C(49) 1.321(7)
O(56) C(55) 1.372(7)
N(21) C(20) 1.505(7)
N(21) C(22) 1.512(8)
N(51) C(50) 1.518(7)
N(51) C(52) 1.453(7)
C(1) C(2) 1.557(8)
C(1) C(8) 1.481(8)
C(1) C(9) 1.551(8)
C(1) C(11) 1.559(9)
C(2) C(3) 1.521(9)
C(3) C(4) 1.490(10)
C(3) C(10) 1.474(9)
C(4) C(5) 1.500(10)
C(5) C(6) 1.470(10)
C(5) C(9) 1.550(9)
C(6) C(7) 1.520(10)
C(7) C(8) 1.560(10)
C(7) C(10) 1.510(10)
C(11) C(12) 1.505(8)
C(12) C(13) 1.501(8)
C(13) C(14) 1.381(8)
C(13) C(18) 1.423(8)
C(14) C(15) 1.424(7)
C(15) C(16) 1.348(8)
C(16) C(17) 1.364(8)
C(16) C(19) 1.536(8)
C(17) C(18) 1.392(8)
C(20) C(24) 1.537(8)
C(20) C(25) 1.470(8)
C(22) C(23) 1.514(9)
C(23) C(24) 1.461(9)
C(31) C(32) 1.499(8)
C(31) C(38) 1.575(8)
C(31) C(39) 1.510(7)
C(31) C(41) 1.536(8)
C(32) C(33) 1.530(9)
C(33) C(34) 1.540(10)
C(33) C(40) 1.570(10)
C(34) C(35) 1.500(10)
C(35) C(36) 1.565(9)
C(35) C(39) 1.493(9)
C(36) C(37) 1.518(9)
C(37) C(38) 1.500(10)
C(37) C(40) 1.530(10)
C(41) C(42) 1.519(8)