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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/2/10/13/2101330.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_2101330
loop_
_publ_author_name
'Stensland, B.'
'Csöregh, I.'
'Högberg, T.'
_publ_section_title
;Conformation of the two potential antipsychotic agents
 (--)-(S)-3-bromo-5,6-dimethoxy-N-[(1-ethyl-2-pyrrolidinyl)methyl]benzamide,
 FLB 457, and its 2-hydroxy analogue, FLB 463
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              847
_journal_page_last               856
_journal_paper_doi               10.1107/S0108768195001790
_journal_volume                  51
_journal_year                    1995
_chemical_formula_sum            'C16 H24 Br2 N2 O3'
_chemical_formula_weight         452.2
_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                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   28.900(2)
_cell_length_b                   8.747(3)
_cell_length_c                   7.5850(10)
_cell_volume                     1917.4(7)
_diffrn_radiation_type           Cu
_diffrn_radiation_wavelength     1.54184
_exptl_absorpt_coefficient_mu    5.535
_exptl_crystal_density_diffrn    1.563
_cod_data_source_file            ab0336.cif
_cod_data_source_block           ab0336a
_cod_original_cell_volume        1917.4
_cod_database_code               2101330
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
C(1) .1030(5) -.1878(17) -.036(2) .042(5)
C(2) .0827(5) -.2838(17) -.153(2) .046(5)
C(3) .0382(6) -.3320(18) -.129(3) .056(6)
Br(3) .01098(8) -.4645(3) -.3021(3) .0894(9)
C(4) .0124(6) -.292(2) .017(2) .057(6)
C(5) .0322(6) -.1956(19) .136(2) .050(6)
O(5) .0087(4) -.1383(15) .2787(16) .071(5)
C(51) -.0389(7) -.173(3) .291(4) .098(10)
C(6) .0780(6) -.145(2) .118(2) .050(6)
O(6) .0956(4) -.0448(15) .2390(13) .056(4)
C(61) .1020(7) -.106(3) .411(2) .074(8)
C(7) .1518(5) -.135(2) -.073(2) .049(6)
O(7) .1704(4) -.1896(16) -.2036(18) .077(5)
N(8) .1712(4) -.0241(14) .0258(15) .044(4)
C(9) .2174(5) .036(2) -.016(2) .046(5)
C(10) .2164(4) .1645(15) -.148(2) .034(4)
C(11) .2650(5) .228(2) -.178(2) .062(6)
C(12) .2710(6) .351(2) -.037(3) .072(8)
C(13) .2244(8) .428(2) -.044(3) .074(8)
N(14) .1907(5) .2994(15) -.0700(18) .053(5)
C(15) .1489(6) .354(2) -.178(3) .076(8)
C(16) .1107(6) .234(2) -.190(3) .080(8)
Br .17184(7) .2602(3) .3470(2) .0728(7)
H(2) .1019(5) -.322(2) -.267(2) .05(1)
H(4) -.0223(6) -.335(2) .036(2) .05(1)
H(51A) -.0549(7) -.092(3) .379(4) .07(2)
H(51B) -.0432(7) -.288(3) .342(4) .07(02)
H(51C) -.0550(7) -.165(3) .162(4) .07(2)
H(61A) .1162(7) -.012(2) .486(2) .07(2)
H(61B) .1286(7) -.190(2) .387(2) .07(2)
H(61C) .0739(7) -.158(2) .483(2) .07(2)
H(8) .1526(4) .0210(10) .138(2) .05(1)
H(9A) .2329(5) .078(2) .105(2) .05(1)
H(9B) .2382(5) -.055(2) -.069(2) .05(1)
H(10) .2009(4) .119(2) -.266(2) .05(1)
H(11A) .2678(5) .278(2) -.308(2) .05(1)
H(11B) .2907(5) .139(2) -.163(2) .05(1)
H(12A) .2987(6) .429(2) -.069(3) .05(1)
H(12B) .2774(6) .301(2) .091(3) .05(1)
H(13A) .2229(8) .507(2) -.153(2) .05(1)
H(13B) .2174(8) .488(2) .077(2) .05(1)
H(14) .1763 .262(2) .054(2) .07(5)
H(15A) .1604(6) .381(2) -.310(3) .05(1)
H(15B) .1349(6) .455(2) -.117(3) .05(1)
H(16A) .0823(6) .287(2) -.260(3) .07(2)
H(16B) .0991(6) .196(2) -.063(3) .07(2)
H(16C) .1233(6) .138(2) -.266(3) .07(2)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(6) C(1) C(7) 123.0(10)
C(2) C(1) C(7) 118.0(10)
C(2) C(1) C(6) 119.0(10)
C(1) C(2) C(3) 121(2)
Br(3) C(3) C(2) 119.0(10)
C(2) C(3) C(4) 123(2)
Br(3) C(3) C(4) 119.0(10)
C(3) C(4) C(5) 117(2)
C(4) C(5) C(6) 122(2)
C(4) C(5) O(5) 123(2)
O(5) C(5) C(6) 115.0(10)
C(5) O(51) C(51) 117.0(10)
C(1) C(6) C(5) 118.0(10)
C(5) C(6) O(6) 119.0(10)
C(1) C(6) O(6) 122.0(10)
C(6) O(6) C(61) 115.0(10)
C(1) C(7) N(8) 120.0(10)
C(1) C(7) O(7) 116.0(10)
O(7) C(7) N(8) 123(2)
C(7) N(8) C(9) 121.0(10)
N(8) C(9) C(10) 113.0(10)
C(9) C(10) N(14) 109.0(10)
C(11) C(10) N(14) 103.0(10)
C(10) C(11) C(12) 105.0(10)
C(11) C(12) C(13) 101(2)
C(12) C(13) N(14) 104(2)
C(10) N(14) C(13) 109.0(10)
C(13) N(14) C(15) 110.0(10)
C(10) N(14) C(15) 115.0(10)
N(14) C(15) C(16) 113(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br(3) C(3) 1.92(2)
C(1) C(2) 1.36(2)
C(1) C(6) 1.42(2)
C(1) C(7) 1.51(2)
C(2) C(3) 1.36(2)
C(3) C(4) 1.38(2)
C(4) C(5) 1.36(2)
C(5) O(5) 1.37(2)
C(5) C(6) 1.40(2)
O(5) C(51) 1.41(2)
C(6) O(6) 1.36(2)
O(6) C(61) 1.42(2)
C(7) O(7) 1.23(2)
C(7) N(8) 1.35(2)
N(8) C(9) 1.47(2)
C(9) C(10) 1.50(2)
C(10) C(11) 1.53(2)
C(10) N(14) 1.51(2)
C(11) C(12) 1.53(3)
C(12) C(13) 1.51(3)
C(13) N(14) 1.50(2)
N(14) C(15) 1.54(2)
C(15) C(16) 1.52(3)
