#------------------------------------------------------------------------------
#$Date: 2018-01-30 16:30:45 +0200 (Tue, 30 Jan 2018) $
#$Revision: 205898 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/10/2001029.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_2001029
loop_
_publ_author_name
'Bruins Slot, H. J.'
'Leusen, F. J. J.'
'van der Haest, A. D.'
'van Bolhuis, F.'
_publ_section_title
;
 Structures of a pair of diastereomeric salts of ephedrine and
 fluoro-substituted cyclic phosphoric acid
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              587
_journal_page_last               590
_journal_paper_doi               10.1107/S0108270191011204
_journal_volume                  48
_journal_year                    1992
_chemical_formula_moiety         'C10 H16 N1 O1,C11 H13 F1 O4 P1'
_chemical_formula_sum            'C21 H29 F N O5 P'
_chemical_formula_weight         425.436
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_cell_angle_alpha                90
_cell_angle_beta                 98.14(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6790(10)
_cell_length_b                   8.1150(10)
_cell_length_c                   13.7970(10)
_cell_volume                     1072.8(2)
_diffrn_radiation_type           Mo
_diffrn_radiation_wavelength     0.71073
_exptl_absorpt_coefficient_mu    0.1617
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             452
_cod_data_source_file            ab0244.cif
_cod_data_source_block           ab0244b
_cod_original_formula_sum        'C21 H29 F1 N1 O5 P1'
_cod_database_code               2001029
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
P(2) .25439(5) .27270 .54797(3) .0141(2)
F(1) .55391(19) -.2100(2) .69966(11) .0509(9)
O(1) .38297(16) .3971(2) .55246(11) .0157(6)
O(3) .28677(14) .1798(2) .65152(10) .0127(6)
O(21) .12465(17) .3709(2) .54867(13) .0160(7)
O(22) .25389(17) .1498(2) .46724(11) .0261(8)
C(4) .4215(2) .0979(3) .67016(14) .0135(8)
C(5) .5383(2) .2293(3) .67327(15) .0142(8)
C(6) .5195(2) .3184(3) .57340(15) .0134(8)
C(41) .42109(16) -.00343(18) .76406(8) .0178(9)
C(42) .49224(16) -.15338(18) .77284(8) .0284(11)
C(43) .49120(16) -.24983(18) .85643(8) .0443(14)
C(44) .41902(16) -.19632(18) .93124(8) .0416(14)
C(45) .34787(16) -.04637(18) .92245(8) .0308(11)
C(46) .34890(16) .05007(18) .83886(8) .0246(10)
C(51) .5357(3) .3534(3) .75602(17) .0243(10)
C(52) .6817(2) .1430(4) .68343(16) .0144(9)
O(10) .16458(16) .1135(3) .27301(12) .0132(7)
N(2) -.06936(17) .1896(3) .40985(12) .0149(7)
C(1) .0209(2) .0716(3) .26375(15) .0168(8)
C(2) -.0693(2) .2095(3) .30174(14) .0154(8)
C(3) -.0233(3) .3817(3) .27810(18) .0293(11)
C(11) -.03337(15) .0397(2) .15735(8) .0198(9)
C(12) -.15916(15) -.0454(2) .13534(8) .0260(11)
C(13) -.21909(15) -.0660(2) .03804(8) .0279(12)
C(14) -.15324(15) -.0016(2) -0.03724(8) .0497(17)
C(15) -.02746(15) .0835(2) -0.01524(8) .0581(19)
C(16) .03248(15) .1041(2) .08206(8) .0342(12)
C(20) -.1860(3) .2768(3) .44794(16) .0284(10)
H(4) .4415(2) .0134(3) .61327(14) ?
H(43) .54629(16) -.36592(18) .86324(8) ?
H(44) .41822(16) -.27099(18) .99595(8) ?
H(45) .29198(16) -.00495(18) .98036(8) ?
H(46) .29382(16) .16616(18) .83206(8) ?
H(61) .5298(2) .2295(3) .51662(15) ?
H(62) .5997(2) .4111(3) .57418(15) ?
H(511) .5488(3) .2897(3) .82546(17) ?
H(512) .4368(3) .4172(3) .74601(17) ?
H(513) .6192(3) .4413(3) .75502(17) ?
H(521) .7001(2) .0784(4) .75250(16) ?
H(522) .7626(2) .2337(4) .68052(16) ?
H(523) .6825(2) .0562(4) .62418(16) ?
H(1) .0122(2) -.0368(3) .30789(15) ?
H(2) -.1742(2) .1958(3) .26381(14) ?
H(10) .205(3) .127(4) .3360(19) ?
H(12) -.21014(15) -.0953(2) .19363(8) ?
H(13) -.31647(15) -.1318(2) .02101(8) ?
H(14) -.19964(15) -.0175(2) -.11257(8) ?
H(15) .02352(15) .1333(2) -.07352(8) ?
H(16) .12986(15) .1699(2) .09910(8) ?
H(21) .02816(17) .2370(3) .44717(12) ?
H(22) -.07732(17) .0599(3) .42566(12) ?
H(31) -0.0242(3) .3929(3) .20000(18) ?
H(32) .0810(3) .4039(3) .31513(18) ?
H(33) -.0939(3) .4711(3) .30208(18) ?
H(201) -.1784(3) .2566(3) .52589(16) ?
H(202) -.2846(3) .2300(3) .41210(16) ?
H(203) -.1791(3) .4071(3) .43361(16) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P(2) O(1) 1.5969(16)
F(1) C(42) 1.326(2)
C(4) C(41) 1.535(2)
C(41) C(42) 1.395(2)
C(44) C(45) 1.395(2)
O(10) C(1) 1.420(3)
C(1) C(11) 1.510(2)
C(12) C(13) 1.3950(16)
P(2) O(3) 1.6065(15)
O(1) C(6) 1.459(3)
C(5) C(6) 1.544(3)
C(41) C(46) 1.3950(19)
C(45) C(46) 1.3950(17)
N(2) C(2) 1.500(3)
C(2) C(3) 1.516(3)
C(13) C(14) 1.3948(18)
P(2) O(21) 1.4884(17)
O(3) C(4) 1.454(3)
C(5) C(51) 1.525(3)
C(42) C(43) 1.3950(17)
N(2) C(20) 1.490(3)
C(11) C(12) 1.395(2)
C(14) C(15) 1.395(2)
P(2) O(22) 1.4946(16)
C(4) C(5) 1.550(3)
C(5) C(52) 1.543(3)
C(43) C(44) 1.3951(19)
C(1) C(2) 1.555(3)
C(11) C(16) 1.3950(18)
C(15) C(16) 1.3950(16)
C(4) H(4) 1.080(3)
C(44) H(44) 1.0799(17)
C(51) H(512) 1.080(4)
C(52) H(523) 1.080(4)
O(10) H(10) 0.91(3)
C(2) H(2) 1.080(3)
C(12) H(12) 1.0801(18)
C(16) H(16) 1.080(2)
C(6) H(61) 1.080(3)
C(45) H(45) 1.0800(19)
C(51) H(513) 1.080(4)
N(2) H(21) 1.080(3)
C(3) H(31) 1.080(3)
C(13) H(13) 1.080(2)
C(20) H(201) 1.080(3)
C(6) H(62) 1.080(3)
C(46) H(46) 1.080(2)
C(52) H(521) 1.080(4)
N(2) H(22) 1.080(3)
C(3) H(32) 1.080(4)
C(14) H(14) 1.0800(16)
C(20) H(202) 1.080(4)
C(43) H(43) 1.080(2)
C(51) H(511) 1.080(3)
C(52) H(522) 1.080(4)
C(1) H(1) 1.080(3)
C(3) H(33) 1.080(4)
C(15) H(15) 1.0797(18)
C(20) H(203) 1.080(3)
