#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/11/2101190.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_2101190
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 <small>L</small>-prolinolium
 α-adamantylacetophenone-p-carboxylate
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              601
_journal_page_last               607
_journal_paper_doi               10.1107/S0108768194002582
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C24 H33 N1 O4 , C24 H33 N1 O4 , H2 O'
_chemical_formula_sum            'C48 H68 N2 O9'
_chemical_formula_weight         817.08
_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                   11.021(2)
_cell_length_b                   56.481(8)
_cell_length_c                   6.8400(10)
_cell_volume                     4257.7(12)
_diffrn_radiation_type           Cu
_diffrn_radiation_wavelength     1.54178
_exptl_absorpt_coefficient_mu    0.66
_exptl_crystal_density_diffrn    1.28
_exptl_crystal_F_000             1768
_cod_data_source_file            br0026.cif
_cod_data_source_block           br0026c
_cod_original_cell_volume        4258(2)
_cod_database_code               2101190
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
O(2H) .583(2) .0322(3) .823(2)
O(12) 1.0300(10) .12340(10) .4570(10)
O(19) .5780(10) .0739(2) 1.042(2)
O(20) .7150(10) .0783(2) 1.270(2)
O(26) .5570(10) .0521(2) .459(2)
O(42) 1.539(2) .1468(2) 1.325(2)
O(49) 1.1230(10) .0848(2) .668(2)
O(50) 1.1650(10) .0653(2) .937(2)
O(56) 1.0220(10) .0318(2) .799(2)
N(21) .3720(10) .0524(2) .169(2)
N(51) .9190(10) .0628(2) .489(2)
C(1) .981(2) .1739(3) .436(3)
C(2) 1.013(2) .1630(2) .636(2)
C(3) 1.139(2) .1702(3) .698(3)
C(4) 1.238(2) .1670(3) .545(3)
C(5) 1.202(2) .1801(3) .361(2)
C(6) 1.189(2) .2073(3) .397(3)
C(7) 1.085(2) .2099(2) .552(3)
C(8) .964(2) .2016(2) .461(3)
C(9) 1.080(2) .1712(2) .287(3)
C(10) 1.125(2) .1979(3) .732(3)
C(11) .881(2) .1559(3) .416(2)
C(12) .9560(10) .1389(3) .562(2)
C(19) .678(2) .0820(3) 1.102(3)
C(20) .344(2) .0554(3) .392(2)
C(22) .377(2) .0268(3) .138(3)
C(23) .294(2) .0157(3) .290(3)
C(24) .315(2) .0314(3) .458(3)
C(25) .452(2) .0671(3) .480(2)
C(41) 1.627(2) .1598(3) 1.022(4)
C(42) 1.541(2) .1464(3) 1.132(3)
C(49) 1.175(2) .0830(3) .837(3)
C(50) .8450(10) .0451(3) .612(3)
C(52) .974(2) .0488(4) .330(3)
C(53) .912(4) .0272(4) .323(5)
C(54) .841(2) .0226(4) .483(4)
C(55) .901(2) .0412(3) .803(3)
C(13) .8785(8) .12580(10) .7060(10)
C(14) .7711(9) .1149(2) .6460(10)
C(15) .7060(7) .1008(2) .776(2)
C(16) .7484(9) .09750(10) .9660(10)
C(17) .8560(10) .1083(2) 1.0260(10)
C(18) .9209(7) .12250(10) .8960(10)
C(43) 1.4318(8) .13300(10) 1.047(2)
C(44) 1.4242(8) .1286(2) .846(2)
C(45) 1.3340(10) .1136(2) .7740(10)
C(46) 1.2523(7) .10290(10) .901(2)
C(47) 1.2598(8) .1073(2) 1.1020(10)
C(48) 1.3500(10) .1223(2) 1.1740(10)
C(31) 1.6110(10) .18640(10) 1.006(2)
C(32) 1.6220(10) .1980(2) 1.2090(10)
C(38) 1.7100(10) .1965(2) .870(2)
C(39) 1.4850(10) .1916(2) .919(2)
C(33) 1.6050(10) .2249(2) 1.1900(10)
C(37) 1.6929(9) .2234(2) .850(2)
C(35) 1.4680(8) .2186(2) .900(2)
C(40) 1.7036(9) .2350(2) 1.054(2)
C(36) 1.5670(10) .2287(2) .7640(10)
C(34) 1.4787(9) .2302(2) 1.103(2)
H(2) .9572 .1694 .7278
H(3) 1.1605 .1624 .8161
H(4A) 1.2471 .1507 .5174
H(4B) 1.3115 .1732 .5950
H(5) 1.2628 .1775 .2648
H(6A) 1.2627 .2138 .4477
H(6B) 1.1682 .2153 .2802
H(7) 1.0769 .2263 .5813
H(8A) .8986 .2049 .5476
H(8B) .9507 .2090 .3396
H(9A) 1.0592 .1799 .1731
H(9B) 1.0883 .1549 .2535
H(10A) 1.0675 .2007 .8314
H(10B) 1.2016 .2042 .7695
H(11A) .8714 .1497 .2875
H(11B) .8049 .1608 .4651
H(12) 1.0626 .1046 .5182
H(14) .7426 .1171 .5160
H(15) .6335 .0933 .7349
H(17) .8853 .1061 1.1555
H(18) .9944 .1299 .9366
H(20) .2759 .0656 .4087
H(21A) .4479 .0594 .1377
H(21B) .3099 .0594 .0932
H(22A) .4568 .0211 .1555
H(22B) .3486 .0230 .0113
H(23A) .3165 -.0001 .3188
H(23B) .2111 .0161 .2498
H(24A) .3807 .0255 .5331
H(24B) .2440 .0321 .5366
H(25A) .4671 .0817 .4158
H(25B) .4387 .0697 .6146
H(26) .6322 .0616 .4305
H(32A) 1.7003 .1948 1.2614
H(32B) 1.5618 .1918 1.2923
H(33) 1.6120 .2322 1.3143
H(34A) 1.4182 .2240 1.1865
H(34B) 1.4684 .2469 1.0904
H(35) 1.3903 .2219 .8463
H(36A) 1.5600 .2217 .6380
H(36B) 1.5562 .2454 .7515
H(37) 1.7537 .2298 .7654
H(38A) 1.7879 .1934 .9220
H(38B) 1.7033 .1894 .7437
H(39A) 1.4787 .1846 .7938
H(39B) 1.4247 .1855 1.0030
H(40A) 1.6931 .2518 1.0409
H(40B) 1.7816 .2320 1.1060
H(41A) 1.7035 .1573 1.0809
H(41B) 1.6260 .1538 .8938
H(44) 1.4803 .1358 .7598
H(45) 1.3296 .1105 .6374
H(47) 1.2034 .1000 1.1885
H(48) 1.3541 .1253 1.3109
H(50) .7650 .0511 .6306
H(51A) .9793 .0701 .5669
H(51B) .8665 .0747 .4365
H(52A) .9640 .0573 .2103
H(52B) 1.0581 .0471 .3565
H(53A) .8679 .0270 .2100
H(53B) .9758 .0156 .3203
H(54A) .8695 .0094 .5523
H(54B) .7603 .0199 .4382
H(55A) .9043 .0557 .8707
H(55B) .8544 .0301 .8720
H(56) 1.0837 .0464 .8049
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) 105.0(10)
C(50) N(51) C(52) 106.0(10)
C(2) C(1) C(8) 109.0(10)
C(2) C(1) C(9) 114.0(10)
C(2) C(1) C(11) 89.0(10)
C(8) C(1) C(9) 105.0(10)
C(8) C(1) C(11) 126.0(10)
C(9) C(1) C(11) 114.0(10)
C(1) C(2) C(3) 111.0(10)
C(1) C(2) C(12) 88.0(10)
C(3) C(2) C(12) 133.0(10)
C(2) C(3) C(4) 116.0(10)
C(2) C(3) C(10) 103.0(10)
C(4) C(3) C(10) 107.0(10)
C(3) C(4) C(5) 109.0(10)
C(4) C(5) C(6) 112.0(10)
C(4) C(5) C(9) 110.0(10)
C(6) C(5) C(9) 107.0(10)
C(5) C(6) C(7) 106.0(10)
C(6) C(7) C(8) 109(2)
C(6) C(7) C(10) 108(2)
C(8) C(7) C(10) 117.0(10)
C(1) C(8) C(7) 104.0(10)
C(1) C(9) C(5) 113.0(10)
C(3) C(10) C(7) 111.0(10)
C(1) C(11) C(12) 88.0(10)
O(12) C(12) C(2) 118.0(10)
O(12) C(12) C(11) 111.0(10)
O(12) C(12) C(13) 111.0(10)
C(2) C(12) C(11) 84.0(10)
C(2) C(12) C(13) 116.0(10)
C(11) C(12) C(13) 114.0(10)
O(19) C(19) O(20) 122(2)
O(19) C(19) C(16) 118.0(10)
O(20) C(19) C(16) 120(2)
N(21) C(20) C(24) 104.0(10)
N(21) C(20) C(25) 106.0(10)
C(24) C(20) C(25) 117(2)
N(21) C(22) C(23) 107.0(10)
C(22) C(23) C(24) 101.0(10)
C(20) C(24) C(23) 111(2)
O(26) C(25) C(20) 110.0(10)
C(42) C(41) C(31) 119(2)
O(42) C(42) C(41) 122(2)
O(42) C(42) C(43) 112(2)
C(41) C(42) C(43) 125(2)
O(49) C(49) O(50) 122(2)
O(49) C(49) C(46) 117.0(10)
O(50) C(49) C(46) 120(2)
N(51) C(50) C(54) 104.0(10)
N(51) C(50) C(55) 111.0(10)
C(54) C(50) C(55) 113(2)
N(51) C(52) C(53) 107(2)
C(52) C(53) C(54) 115(2)
C(50) C(54) C(53) 106(2)
O(56) C(55) C(50) 116.0(10)
C(12) C(13) C(14) 120.3(9)
C(12) C(13) C(18) 119.4(9)
C(42) C(43) C(44) 120.0(10)
C(42) C(43) C(48) 119.0(10)
C(41) C(31) C(39) 109.0(10)
C(19) C(16) C(15) 119.0(10)
C(19) C(16) C(17) 121.0(10)
C(41) C(31) C(32) 110.0(10)
C(41) C(31) C(38) 109.0(10)
C(49) C(46) C(45) 121.0(10)
C(49) C(46) C(47) 118.0(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O(12) C(12) 1.40(2)
O(19) C(19) 1.26(2)
O(20) C(19) 1.24(2)
O(26) C(25) 1.45(2)
O(42) C(42) 1.32(2)
O(49) C(49) 1.29(2)
O(50) C(49) 1.21(2)
O(56) C(55) 1.43(2)
N(21) C(20) 1.56(2)
N(21) C(22) 1.47(2)
N(51) C(50) 1.54(2)
N(51) C(52) 1.47(2)
C(1) C(2) 1.53(2)
C(1) C(8) 1.59(2)
C(1) C(9) 1.50(3)
C(1) C(11) 1.51(2)
C(2) C(12) 1.58(2)
C(3) C(4) 1.52(3)
C(3) C(10) 1.59(2)
C(4) C(5) 1.52(3)
C(5) C(6) 1.56(2)
C(5) C(9) 1.52(3)
C(6) C(7) 1.56(3)
C(7) C(8) 1.54(3)
C(7) C(10) 1.47(3)
C(11) C(12) 1.61(2)
C(12) C(13) 1.50(2)
C(19) C(16) 1.49(2)
C(20) C(24) 1.47(2)
C(20) C(25) 1.49(3)
C(22) C(23) 1.52(3)
C(23) C(24) 1.47(3)
C(41) C(42) 1.43(3)
C(41) C(31) 1.51(2)
C(42) C(43) 1.54(2)
C(49) C(46) 1.48(2)
C(50) C(54) 1.55(3)
C(50) C(55) 1.47(2)
C(52) C(53) 1.40(4)
C(53) C(54) 1.37(4)
