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#$Date: 2018-01-30 14:30:45 +0000 (Tue, 30 Jan 2018) $
#$Revision: 205898 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/13/2101331.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_2101331
loop_
_publ_author_name
'Stensland, B.'
'Cs\"oregh, I.'
'H\"ogberg, T.'
_publ_section_title
;Conformation of the two potential antipsychotic agents
 (--)-(<i>S</i>)-3-bromo-5,6-dimethoxy-<i>N</i>-[(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            'C17 H27 Br N2 O7 S'
_chemical_formula_weight         483.4
_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                90.0
_cell_angle_beta                 93.44(5)
_cell_angle_gamma                90.0
_cell_formula_units_Z            2
_cell_length_a                   15.264(5)
_cell_length_b                   8.087(4)
_cell_length_c                   8.541(3)
_cell_volume                     1052.4(7)
_diffrn_radiation_type           Cu
_diffrn_radiation_wavelength     1.54184
_exptl_absorpt_coefficient_mu    3.941
_exptl_crystal_density_diffrn    1.525
_cod_data_source_file            ab0336.cif
_cod_data_source_block           ab0336b
_cod_original_cell_volume        1052.4
_cod_original_formula_sum        'C17 H27 Br1 N2 O7 S1'
_cod_database_code               2101331
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
C(1) -.1974(3) -.7645(5) -.2436(5) .0360(10)
C(2) -.1502(3) -.8599(6) -.1292(5) .0390(10)
O(2) -.1815(3) -.8942(6) .0119(4) .0540(10)
C(3) -.0686(3) -.9225(6) -.1621(6) .0430(10)
Br(3) -.00513(4) -1.05600 -.01246(8) .0639(2)
C(4) -.0331(3) -.8938(7) -.3048(7) .048(2)
C(5) -.0773(3) -.7980(7) -.4164(6) .0440(10)
O(5) -.0428(4) -.7522(6) -.5551(6) .0600(10)
C(51) .0176(5) -.8574(12) -.6184(8) .076(3)
C(6) -.1596(3) -.7337(6) -.3882(5) .0360(10)
O(6) -.2024(2) -.6356(5) -.4973(4) .0420(10)
C(61) -.2256(5) -.7069(10) -.6469(7) .061(2)
C(7) -.2867(3) -.7044(6) -.2045(5) .0390(10)
O(7) -.3159(3) -.7412(6) -.0771(5) .0600(10)
N(8) -.3347(2) -.6144(6) -.3080(5) .0390(10)
C(9) -.4217(3) -.5535(8) -.2737(6) .0420(10)
C(10) -.4206(3) -.4000(7) -.1698(5) .0390(10)
C(11) -.5129(3) -.3427(9) -.1346(7) .056(2)
C(12) -.5330(5) -.2106(14) -.2573(13) .092(4)
C(13) -.4495(5) -.1206(10) -.2741(10) .071(2)
N(14) -.3805(3) -.2524(6) -.2526(5) .0430(10)
C(15) -.2993(4) -.1817(8) -.1711(3) .056(2)
C(16) -.2234(4) -.2994(11) -.1589(10) .072(2)
S -.67020(10) .2757(2) -.33670(10) .0489(4)
O(1S) -.6494(4) .4360(9) -.4042(7) .084(2)
O(2S) -.6582(4) .1432(6) -.4488(5) .065(2)
O(3S) -.6249(4) .2458(10) -.1897(5) .088(2)
C(1S) -.7840(5) .2825(16) -.3048(11) .091(3)
H(2) -.2390 -.8171 .0210 .09(3)
H(4) .0295(3) -.9473(7) -.3290(7) .076(6)
H(51A) .0341(5) -.7949(12) -.7244(8) .103(9)
H(51B) -.0067(5) -.9799(12) -.6471(8) .103(9)
H(51C) .0753(5) -.8668(12) -.5395(8) .103(9)
H(61A) -.2601(5) -.6051(10) -.7045(7) .103(9)
H(61B) -.2706(5) -.8081(10) -.6324(7) .109(9)
H(61C) -.1732(5) -.7470(10) -.7174(7) .103(9)
H(8) -.3089(2) -.5858(6) -.4198(5) .076(6)
H(9A) -.4572(3) -.5240(8) -.3834(6) .076(6)
H(9B) -.4554(3) -.6509(8) -.2152(6) .076(6)
H(10) -.3830(3) -.4354(7) -.0639(5) .076(6)
H(11A) -.5138(3) -.2918(9) -.0178(7) .076(6)
H(11B) -.5592(3) -.4435(9) -.1469(7) .076(6)
H(12A) -.5829(5) -.1277(14) -.2193(13) .076(6)
H(12B) -.5551(5) -.2667(14) -.3675(13) .076(6)
H(13A) -.4483(5) -.0647(10) -.3888(10) .076(6)
H(13B) -.4403(5) -.0262(10) -.1852(10) .076(6)
H(14) -.3653 -.2994 -.3553 .06(2)
H(15A) -.2798(4) -.0740(8) -.2353(7) .076(6)
H(15B) -.3146(4) -.1457(8) -.0541(7) .076(6)
H(16A) -.1713(4) -.2335(11) -.0944(10) .103(9)
H(16B) -.2047(4) -.3225(11) -.2768(10) .103(9)
H(16C) -.2349(4) -.4157(11) -.1014(10) .103(9)
H(1S) -.8205(5) .3034(16) -.4152(11) .103(9)
H(2S) -.7963(5) .3824(16) -.2251(11) .103(9)
H(3S) -.8044(5) .1670(16) -.2550(11) .103(9)
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) 124.0(4)
C(2) C(1) C(7) 117.4(4)
C(2) C(1) C(6) 118.8(4)
C(1) C(2) C(3) 119.1(4)
C(1) C(2) O(2) 122.4(5)
O(2) C(2) C(3) 118.4(4)
Br(3) C(3) C(2) 120.0(4)
C(2) C(3) C(4) 121.5(5)
Br(3) C(3) C(4) 118.6(4)
C(3) C(4) C(5) 120.2(5)
C(4) C(5) C(6) 120.0(5)
C(4) C(5) O(5) 123.5(5)
O(5) C(5) C(6) 116.4(5)
C(5) O(51) C(51) 117.9(6)
C(1) C(6) C(5) 120.3(4)
C(5) C(6) O(6) 120.0(4)
C(1) C(6) O(6) 119.7(4)
C(6) O(6) C(61) 117.5(5)
C(1) C(7) N(8) 120.0(4)
C(1) C(7) O(7) 119.8(5)
O(7) C(7) N(8) 120.5(5)
C(7) N(8) C(9) 121.5(4)
N(8) C(9) C(10) 114.3(4)
C(9) C(10) N(14) 110.8(4)
C(9) C(10) C(11) 112.5(4)
C(11) C(10) N(14) 104.6(4)
C(10) C(11) C(12) 103.2(2)
C(11) C(12) C(13) 105.9(7)
C(12) C(13) N(14) 103.9(7)
C(10) N(14) C(13) 108.2(4)
C(13) N(14) C(15) 109.9(5)
C(10) N(14) C(15) 115.1(4)
N(14) C(15) C(16) 113.9(6)
O(3S) S C(1S) 107.4(4)
O(2S) S C(1S) 106.7(4)
O(2S) S O(3S) 112.5(4)
O(1S) S O(3S) 113.2(4)
O(1S) S O(2S) 110.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br(3) C(3) 1.895(5)
C(1) C(2) 1.409(6)
C(1) C(6) 1.417(7)
C(1) C(7) 1.503(7)
C(2) O(2) 1.352(6)
C(2) C(3) 1.388(7)
C(3) C(4) 1.382(8)
C(4) C(5) 1.374(8)
C(5) O(5) 1.376(7)
C(5) C(6) 1.394(7)
O(5) C(51) 1.388(10)
C(6) O(6) 1.361(6)
O(6) C(61) 1.427(7)
C(7) O(7) 1.237(7)
C(7) N(8) 1.331(6)
N(8) C(9) 1.462(6)
C(9) C(10) 1.526(8)
C(10) C(11) 1.531(7)
C(10) N(14) 1.533(7)
C(11) C(12) 1.515(13)
C(12) C(13) 1.482(12)
C(13) N(14) 1.501(9)
N(14) C(15) 1.498(7)
C(15) C(16) 1.499(10)
S O(1S) 1.462(7)
S O(2S) 1.456(5)
S O(3S) 1.417(5)
S C(1S) 1.774(7)