#------------------------------------------------------------------------------
#$Date: 2017-03-27 08:13:23 +0300 (Mon, 27 Mar 2017) $
#$Revision: 194538 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/10/2001068.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_2001068
loop_
_publ_author_name
'Bruins Slot, H. J.'
'Leusen, F. J. J.'
'van der Haest, A. D.'
'Smits, J. M. M.'
_publ_section_title
;
 Structures of a pair of diastereomeric salts of ephedrine and
 bromo-substituted cyclic phosphoric acid
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              372
_journal_page_last               376
_journal_paper_doi               10.1107/S010827019100906X
_journal_volume                  48
_journal_year                    1992
_chemical_formula_moiety         'C11 H13 Br1 O4 P1,C10 H16 N1 O1,2(H2 O1)'
_chemical_formula_sum            'C21 H33 Br N O7 P'
_chemical_formula_weight         522.372
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_cell_angle_alpha                90
_cell_angle_beta                 102.013(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.9469(9)
_cell_length_b                   7.7456(3)
_cell_length_c                   15.7571(5)
_cell_volume                     2500.54(17)
_diffrn_radiation_type           Cu
_diffrn_radiation_wavelength     1.54184
_exptl_absorpt_coefficient_mu    3.1931
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_F_000             1087.86
_cod_data_source_file            ab0223.cif
_cod_data_source_block           ab0223b
_cod_depositor_comments
;
 Marking attached hydrogen atoms.

 Antanas Vaitkus,
 2017-03-27
;
_cod_original_cell_volume        2500.5(2)
_cod_original_formula_sum        'C21 H33 Br1 N1 O7 P1'
_cod_database_code               2001068
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_attached_hydrogens
Br(1) .36794(4) -.4046 .41017(5) .1039(3) 0
P(2) .36075(5) .06879(17) .14384(5) .0560(3) 0
O(1) .43836(13) .0776(5) .15598(17) .0672(9) 0
O(3) .35072(12) .0649(4) .24158(15) .0550(8) 0
O(21) .33339(18) .2329(5) .1040(2) .0719(11) 0
O(22) .33633(18) -.0963(5) .1001(2) .0684(11) 0
C(4) .38818(18) -.0582(6) .3005(2) .0544(11) 0
C(5) .4618(2) -.0271(8) .3067(3) .0665(14) 0
C(6) .4750(2) -.0450(8) .2148(3) .0755(18) 0
C(41) .36317(15) -.0367(4) .38583(15) .0560(11) 0
C(42) .35418(15) -.1764(4) .43802(15) .0674(14) 0
C(43) .33152(15) -.1488(4) .51413(15) .0837(19) 0
C(44) .31786(15) .0184(4) .53805(15) .084(2) 0
C(45) .32685(15) .1580(4) .48586(15) .0802(19) 0
C(46) .34951(15) .1305(4) .40975(15) .0669(16) 0
C(51) .4842(3) .1484(10) .3435(4) .092(2) 0
C(52) .5011(3) -.1727(12) .3607(4) .099(3) 0
O(10) .26677(16) -.3751(5) .1384(3) .0746(11) 0
N(2) .20307(18) -.6783(5) .0727(2) .0585(10) 0
C(1) .1980(2) -.3790(6) .1230(3) .0611(14) 0
C(2) .1787(2) -.5659(6) .1367(3) .0648(16) 0
C(3) .2057(4) -.6316(8) .2281(3) .093(3) 0
C(11) .17005(14) -.2586(4) .18191(18) .0615(12) 0
C(12) .20941(14) -.1946(4) .25783(18) .0680(16) 0
C(13) .18291(14) -.0857(4) .31199(18) .0804(19) 0
C(14) .11703(14) -.0407(4) .29023(18) .095(2) 0
C(15) .07767(14) -.1046(4) .21431(18) .096(3) 0
C(16) .10417(14) -.2136(4) .16014(18) .0843(19) 0
C(20) .1781(3) -.8568(7) .0676(4) .0829(19) 0
O(101) .4122(4) .5391(13) .1370(6) .173(3) 2
O(102) .0 -.474(3) .0 .226(7) 2
O(103) .5 -.334(3) .0 .258(8) 2
H(4) .38193(18) -.1914(6) .2802(2) ? 0
H(43) .32456(15) -.2569(4) .55454(15) ? 0
H(44) .30031(15) .0397(4) .59697(15) ? 0
H(45) .31627(15) .2875(4) .50437(15) ? 0
H(46) .35647(15) .2386(4) .36934(15) ? 0
H(61) .4616(2) -.1736(8) .1911(3) ? 0
H(62) .5263(2) -.0246(8) .2174(3) ? 0
H(511) .4748(3) .1601(10) .4081(4) ? 0
H(512) .4579(3) .2480(10) .3026(4) ? 0
H(513) .5359(3) .1624(10) .3462(4) ? 0
H(521) .4938(3) -.1670(12) .4265(4) ? 0
H(522) .5523(3) -.1567(12) .3608(4) ? 0
H(523) .4846(3) -.2962(12) .3325(4) ? 0
H(1) .1782(2) -.3346(6) .0578(3) ? 0
H(2) .1262(2) -.5704(6) .1270(3) ? 0
H(10) .275(3) -.265(6) .122(4) ? 0
H(12) .26041(14) -.2294(4) .27468(18) ? 0
H(13) .21338(14) -.0361(4) .37077(18) ? 0
H(14) .09651(14) .0437(4) .33216(18) ? 0
H(15) .02667(14) -.0698(4) .19746(18) ? 0
H(16) .07370(14) -.2631(4) .10137(18) ? 0
H(21) .25567(18) -.6833(5) .0910(2) ? 0
H(22) .18874(18) -.6203(5) .0093(2) ? 0
H(31) .1882(4) -.5508(8) .2743(3) ? 0
H(32) .2584(4) -.6279(8) .2411(3) ? 0
H(33) .1896(4) -.7628(8) .2339(3) ? 0
H(201) .1980(3) -.9282(7) .0202(4) ? 0
H(202) .1255(3) -.8550(7) .0486(4) ? 0
H(203) .1924(3) -.9180(7) .1303(4) ? 0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br(1) C(42) 1.858(3)
P(2) O(1) 1.598(3)
P(2) O(3) 1.597(2)
P(2) O(21) 1.479(4)
P(2) O(22) 1.492(4)
O(1) C(6) 1.433(6)
O(3) C(4) 1.443(5)
C(4) C(5) 1.544(6)
C(4) C(41) 1.550(4)
C(5) C(6) 1.536(6)
C(5) C(51) 1.514(10)
C(5) C(52) 1.543(10)
C(41) C(42) 1.395(4)
C(41) C(46) 1.395(4)
C(42) C(43) 1.395(4)
C(43) C(44) 1.395(4)
C(44) C(45) 1.395(4)
C(45) C(46) 1.395(4)
O(10) C(1) 1.410(6)
N(2) C(2) 1.500(6)
N(2) C(20) 1.474(7)
C(1) C(2) 1.530(7)
C(1) C(11) 1.517(5)
C(2) C(3) 1.521(7)
C(11) C(12) 1.395(4)
C(11) C(16) 1.395(4)
C(12) C(13) 1.395(4)
C(13) C(14) 1.395(4)
C(14) C(15) 1.395(4)
C(15) C(16) 1.395(4)
