#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:19:39 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178381 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/03/4020353.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4020353
loop_
_publ_author_name
'James C. Anderson'
'Gareth P. Howell'
'Ron M. Lawrence'
'Claire S. Wilson'
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5665
_journal_page_last               5670
_journal_paper_doi               10.1021/jo050762i
_journal_volume                  70
_journal_year                    2005
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H20 N2 O S'
_chemical_formula_weight         312.42
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 98.244(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3906(5)
_cell_length_b                   12.5141(9)
_cell_length_c                   18.0913(12)
_cell_measurement_temperature    120(2)
_cell_volume                     1655.9(2)
_diffrn_ambient_temperature      120(2)
_exptl_crystal_density_diffrn    1.253
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4020353
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7099(7) 0.0719(5) 0.1943(3) 0.0911(15) Uani 1 1 d DU . .
N2 N 0.7860(8) -0.0133(4) 0.1618(2) 0.1072(16) Uani 1 1 d DU B .
H2A H 0.8895 -0.0407 0.1800 0.129 Uiso 1 1 calc R . .
C3 C 0.6794(10) -0.0522(6) 0.0955(4) 0.113(2) Uani 1 1 d DU . .
H3A H 0.6371 -0.1256 0.1009 0.136 Uiso 0.50 1 calc PR A 1
H3' H 0.6201 -0.1144 0.1145 0.136 Uiso 0.50 1 calc PR A 2
C4 C 0.5173(9) 0.0307(6) 0.0843(3) 0.0987(16) Uani 1 1 d DU B .
H4A H 0.4028 -0.0075 0.0874 0.118 Uiso 1 1 calc R . .
N5 N 0.5550(7) 0.0996(4) 0.1477(2) 0.0981(14) Uani 1 1 d DU B .
C6 C 0.5005(9) 0.0872(6) 0.0110(3) 0.0987(16) Uani 1 1 d U . .
C7 C 0.3676(10) 0.0575(8) -0.0488(3) 0.118(2) Uani 1 1 d U B .
H7A H 0.2823 0.0046 -0.0430 0.141 Uiso 1 1 calc R . .
C8 C 0.3663(11) 0.1104(11) -0.1189(4) 0.138(3) Uani 1 1 d U . .
H8A H 0.2750 0.0939 -0.1582 0.166 Uiso 1 1 calc R B .
C9 C 0.4965(14) 0.1852(10) -0.1298(4) 0.143(3) Uani 1 1 d U B .
H9A H 0.4993 0.2156 -0.1766 0.172 Uiso 1 1 calc R . .
C10 C 0.6211(12) 0.2132(8) -0.0702(4) 0.126(2) Uani 1 1 d U . .
H10B H 0.7081 0.2647 -0.0765 0.151 Uiso 1 1 calc R B .
C11 C 0.6228(10) 0.1692(6) -0.0025(4) 0.1045(18) Uani 1 1 d U B .
H11B H 0.7075 0.1935 0.0370 0.125 Uiso 1 1 calc R . .
C12 C 0.8287(18) -0.0429(11) 0.0345(8) 0.100(3) Uiso 0.50 1 d PDU B 1
H12C H 0.7630 -0.0363 -0.0157 0.120 Uiso 0.50 1 calc PR B 1
H12D H 0.9033 0.0205 0.0452 0.120 Uiso 0.50 1 calc PR B 1
C13 C 0.950(2) -0.1405(12) 0.0391(9) 0.116(4) Uiso 0.50 1 d PDU B 1
H13D H 1.0324 -0.1350 0.0028 0.174 Uiso 0.50 1 calc PR B 1
H13E H 0.8761 -0.2034 0.0293 0.174 Uiso 0.50 1 calc PR B 1
H13F H 1.0191 -0.1453 0.0882 0.174 Uiso 0.50 1 calc PR B 1
C12' C 0.7509(17) -0.0956(11) 0.0375(7) 0.096(3) Uiso 0.50 1 d PDU B 2
H12A H 0.8142 -0.0396 0.0145 0.115 Uiso 0.50 1 calc PR B 2
H12B H 0.6503 -0.1193 0.0007 0.115 Uiso 0.50 1 calc PR B 2
C13' C 0.883(2) -0.1891(13) 0.0545(11) 0.131(5) Uiso 0.50 1 d PDU B 2
H13G H 0.9213 -0.2137 0.0090 0.196 Uiso 0.50 1 calc PR B 2
H13H H 0.8222 -0.2462 0.0767 0.196 Uiso 0.50 1 calc PR B 2
H13I H 0.9872 -0.1663 0.0885 0.196 Uiso 0.50 1 calc PR B 2
S14 S 0.7900(2) 0.12704(19) 0.27574(8) 0.1153(8) Uani 1 1 d U C 2
C15 C 0.4407(9) 0.1867(6) 0.1592(3) 0.0991(16) Uani 1 1 d U B 2
C16 C 0.4997(10) 0.2897(6) 0.1556(3) 0.0981(16) Uani 1 1 d U B 2
H16B H 0.6201 0.3028 0.1488 0.118 Uiso 1 1 calc R B 2
C17 C 0.3804(10) 0.3775(6) 0.1620(3) 0.1055(18) Uani 1 1 d U B 2
H17B H 0.4219 0.4475 0.1611 0.127 Uiso 1 1 calc R B 2
C18 C 0.2075(10) 0.3558(8) 0.1695(4) 0.1127(19) Uani 1 1 d U B 2
C19 C 0.1440(11) 0.2596(10) 0.1726(4) 0.129(2) Uani 1 1 d U B 2
H19B H 0.0218 0.2502 0.1781 0.154 Uiso 1 1 calc R B 2
C20 C 0.2572(11) 0.1670(8) 0.1678(4) 0.120(2) Uani 1 1 d U B 2
H20B H 0.2118 0.0980 0.1703 0.144 Uiso 1 1 calc R B 2
O21 O 0.0776(8) 0.4359(6) 0.1750(3) 0.1358(18) Uani 1 1 d U B 2
C22 C 0.1365(14) 0.5454(9) 0.1763(5) 0.144(3) Uani 1 1 d U B 2
H22D H 0.0338 0.5914 0.1789 0.216 Uiso 1 1 calc R B 2
H22E H 0.1881 0.5608 0.1317 0.216 Uiso 1 1 calc R B 2
H22F H 0.2271 0.5571 0.2191 0.216 Uiso 1 1 calc R B 2
C1A C 0.2317(8) 0.9005(5) 0.3167(3) 0.0708(14) Uiso 0.80 1 d PDU D 1
N2A N 0.1203(11) 0.9616(6) 0.3552(3) 0.108(3) Uiso 0.80 1 d PDU D 1
H2AA H 0.0404 1.0060 0.3341 0.130 Uiso 0.80 1 calc PR D 1
C1B C 0.181(3) 0.8613(17) 0.3120(10) 0.091(8) Uiso 0.20 1 d PDU D 2
N2B N 0.0933(19) 0.9312(12) 0.3568(5) 0.043(4) Uiso 0.20 1 d PDU D 2
H2BA H 0.0012 0.9680 0.3363 0.051 Uiso 0.20 1 calc PR D 2
C3A C 0.1526(10) 0.9428(6) 0.4350(3) 0.1057(17) Uani 1 1 d DU . .
H3AA H 0.0387 0.9215 0.4527 0.127 Uiso 1 1 calc R D 1
C4A C 0.2881(9) 0.8475(6) 0.4409(3) 0.0996(16) Uani 1 1 d DU D .
H4AA H 0.2185 0.7807 0.4402 0.119 Uiso 1 1 calc R E 1
N5A N 0.3668(11) 0.8561(6) 0.3703(3) 0.096(3) Uiso 0.80 1 d PDU D 1
N5B N 0.326(3) 0.8323(18) 0.3673(6) 0.059(6) Uiso 0.20 1 d PDU D 2
C6A C 0.4405(9) 0.8455(6) 0.5076(3) 0.1018(17) Uani 1 1 d U . .
C7A C 0.5978(10) 0.9112(6) 0.5085(4) 0.1110(19) Uani 1 1 d U D .
H7AA H 0.6114 0.9536 0.4674 0.133 Uiso 1 1 calc R . .
C8A C 0.7294(11) 0.9117(8) 0.5703(4) 0.127(2) Uani 1 1 d U . .
H8AA H 0.8314 0.9558 0.5724 0.153 Uiso 1 1 calc R D .
C9A C 0.7075(12) 0.8468(9) 0.6279(4) 0.137(3) Uani 1 1 d U D .
H9AA H 0.7998 0.8448 0.6686 0.164 Uiso 1 1 calc R . .
C10A C 0.5614(10) 0.7857(9) 0.6297(4) 0.127(3) Uani 1 1 d U . .
H10A H 0.5505 0.7452 0.6719 0.153 Uiso 1 1 calc R D .
C11A C 0.4303(10) 0.7825(7) 0.5707(3) 0.1069(18) Uani 1 1 d U D .
H11A H 0.3304 0.7376 0.5717 0.128 Uiso 1 1 calc R . .
C12A C 0.2197(12) 1.0439(6) 0.4702(4) 0.117(2) Uani 1 1 d U D .
H12E H 0.3185 1.0706 0.4454 0.140 Uiso 1 1 calc R . .
H12F H 0.2688 1.0304 0.5220 0.140 Uiso 1 1 calc R . .
C13A C 0.0673(12) 1.1314(7) 0.4669(4) 0.126(3) Uani 1 1 d U . .
H13A H 0.1196 1.1966 0.4882 0.189 Uiso 1 1 calc R D .
H13B H -0.0266 1.1076 0.4947 0.189 Uiso 1 1 calc R . .
H13C H 0.0154 1.1435 0.4159 0.189 Uiso 1 1 calc R . .
S14A S 0.2133(3) 0.8885(2) 0.22551(8) 0.1012(8) Uani 0.80 1 d PDU D 1
S14B S 0.1413(13) 0.8345(8) 0.2328(6) 0.098(3) Uiso 0.20 1 d PDU D 2
C15A C 0.4852(9) 0.7746(6) 0.3480(3) 0.0963(16) Uani 1 1 d U . .
C16A C 0.4447(10) 0.6662(6) 0.3526(3) 0.1015(17) Uani 1 1 d U D .
H16A H 0.3322 0.6452 0.3651 0.122 Uiso 1 1 calc R . .
C17A C 0.5697(10) 0.5901(6) 0.3389(3) 0.1014(17) Uani 1 1 d U . .
H17A H 0.5400 0.5182 0.3421 0.122 Uiso 1 1 calc R D .
C18A C 0.7351(9) 0.6173(6) 0.3208(3) 0.0972(16) Uani 1 1 d U D .
C19A C 0.7785(11) 0.7258(7) 0.3157(4) 0.1127(19) Uani 1 1 d U . .
H19A H 0.8919 0.7456 0.3035 0.135 Uiso 1 1 calc R D .
C20A C 0.6535(10) 0.8035(6) 0.3286(3) 0.1023(17) Uani 1 1 d U D .
H20A H 0.6824 0.8754 0.3243 0.123 Uiso 1 1 calc R . .
O21A O 0.8645(7) 0.5461(4) 0.3059(2) 0.1102(14) Uani 1 1 d U . .
C22A C 0.8136(11) 0.4343(7) 0.3086(4) 0.116(2) Uani 1 1 d U D .
H22A H 0.9146 0.3904 0.2993 0.174 Uiso 1 1 calc R . .
H22B H 0.7104 0.4205 0.2712 0.174 Uiso 1 1 calc R . .
H22C H 0.7822 0.4179 0.3570 0.174 Uiso 1 1 calc R . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N5 1.365(6) . ?
C1 N2 1.376(6) . ?
C1 S14 1.658(5) . ?
N2 C3 1.423(6) . ?
C3 C12' 1.354(14) . ?
C3 C4 1.575(10) . ?
C3 C12 1.672(16) . ?
C4 N5 1.429(6) . ?
C4 C6 1.493(9) . ?
N5 C15 1.413(9) . ?
C6 C7 1.404(9) . ?
C6 C11 1.411(10) . ?
C7 C8 1.430(11) . ?
C8 C9 1.377(14) . ?
C9 C10 1.360(12) . ?
C10 C11 1.341(10) . ?
C12 C13 1.511(15) . ?
C12' C13' 1.525(16) . ?
C15 C16 1.365(10) . ?
C15 C20 1.409(10) . ?
C16 C17 1.423(10) . ?
C17 C18 1.332(11) . ?
C18 C19 1.296(13) . ?
C18 O21 1.401(10) . ?
C19 C20 1.439(13) . ?
O21 C22 1.437(13) . ?
C1A N2A 1.383(6) . ?
C1A N5A 1.402(6) . ?
C1A S14A 1.643(6) . ?
N2A C3A 1.447(7) . ?
C1B N5B 1.408(9) . ?
C1B N2B 1.410(9) . ?
C1B S14B 1.46(2) . ?
N2B C3A 1.427(8) . ?
C3A C12A 1.470(10) . ?
C3A C4A 1.552(9) . ?
C4A N5B 1.413(8) . ?
C4A N5A 1.481(7) . ?
C4A C6A 1.529(9) . ?
N5A C15A 1.439(9) . ?
N5B C15A 1.462(17) . ?
C6A C11A 1.399(9) . ?
C6A C7A 1.422(10) . ?
C7A C8A 1.373(11) . ?
C8A C9A 1.350(12) . ?
C9A C10A 1.327(12) . ?
C10A C11A 1.335(10) . ?
C12A C13A 1.566(11) . ?
C15A C20A 1.388(10) . ?
C15A C16A 1.394(11) . ?
C16A C17A 1.374(9) . ?
C17A C18A 1.353(10) . ?
C18A O21A 1.362(8) . ?
C18A C19A 1.401(11) . ?
C19A C20A 1.385(10) . ?
O21A C22A 1.452(10) . ?
