#------------------------------------------------------------------------------
#$Date: 2022-09-14 21:32:59 +0300 (Wed, 14 Sep 2022) $
#$Revision: 277840 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/06/4020643.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_4020643
loop_
_publ_author_name
'Wanlong Jiang'
'Chen Chen'
'Dragan Marinkovic'
'Joe A. Tran'
'Caroline W. Chen'
'L. Melissa Arellano'
'Nicole S. White'
'Fabio C. Tucci'
_publ_section_title
;
 Practical Asymmetric Synthesis of α-Branched
 2-Piperazinylbenzylamines by 1,2-Additions of Organometallic
 Reagents to N-tert-Butanesulfinyl Imines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8924
_journal_page_last               8931
_journal_paper_doi               10.1021/jo051514p
_journal_volume                  70
_journal_year                    2005
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C21 H34 F N3 O3 S), H2 O'
_chemical_formula_sum            'C21 H35 F N3 O3.5 S'
_chemical_formula_weight         436.58
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_cell_angle_alpha                104.9600(10)
_cell_angle_beta                 90.2230(10)
_cell_angle_gamma                98.0370(10)
_cell_formula_units_Z            2
_cell_length_a                   6.4664(3)
_cell_length_b                   12.2820(7)
_cell_length_c                   15.5671(8)
_cell_measurement_temperature    133(2)
_cell_volume                     1181.67(11)
_diffrn_ambient_temperature      133(2)
_exptl_crystal_density_diffrn    1.227
_cod_original_formula_sum        'C21 H35 F N3 O3.50 S'
_cod_database_code               4020643
loop_
_symmetry_equiv_pos_as_xyz
'x, y, 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
S1A S 0.89705(9) 0.06963(5) 0.21414(4) 0.01734(13) Uani 1 1 d . . .
H1A H 1.315(6) 0.054(3) 0.303(2) 0.021(9) Uiso 1 1 d . . .
O2A O 0.7131(3) 0.13392(19) 0.22989(14) 0.0260(4) Uani 1 1 d . . .
H2A H 1.146(9) -0.059(5) 0.270(4) 0.062(15) Uiso 1 1 d . . .
C3A C 1.0023(4) 0.0754(3) 0.32575(17) 0.0213(5) Uani 1 1 d . . .
H3A H 1.238(6) 0.011(4) 0.371(3) 0.036(11) Uiso 1 1 d . . .
C4A C 1.1893(7) 0.0104(4) 0.3131(2) 0.0357(8) Uani 1 1 d . . .
H4A H 0.786(7) -0.063(4) 0.329(3) 0.040(11) Uiso 1 1 d . . .
C5A C 0.8248(7) 0.0147(4) 0.3677(3) 0.0443(10) Uani 1 1 d . . .
H5A H 0.872(6) 0.016(3) 0.425(3) 0.025(9) Uiso 1 1 d . . .
C6A C 1.0630(6) 0.1971(3) 0.3802(2) 0.0291(7) Uani 1 1 d . . .
H6A H 0.707(8) 0.062(4) 0.375(3) 0.051(13) Uiso 1 1 d . . .
N7A N 1.0998(4) 0.14515(19) 0.18031(14) 0.0163(4) Uani 1 1 d . . .
H7A H 1.079(12) 0.186(7) 0.438(6) 0.11(3) Uiso 1 1 d . . .
C8A C 1.1180(4) 0.1179(2) 0.08186(16) 0.0168(5) Uani 1 1 d . . .
H8A H 0.931(7) 0.231(4) 0.379(3) 0.037(11) Uiso 1 1 d . . .
C9A C 1.2938(6) 0.2032(3) 0.06254(19) 0.0268(6) Uani 1 1 d . . .
H9A H 1.186(7) 0.238(4) 0.356(3) 0.045(12) Uiso 1 1 d . . .
C10A C 1.1630(4) -0.0046(2) 0.04994(16) 0.0148(5) Uani 1 1 d . . .
H10A H 1.089(6) 0.212(3) 0.206(2) 0.022(9) Uiso 1 1 d . . .
C11A C 1.3260(4) -0.0367(2) 0.09206(17) 0.0185(5) Uani 1 1 d . . .
H11A H 0.986(5) 0.128(3) 0.055(2) 0.008(7) Uiso 1 1 d . . .
C12A C 1.3585(4) -0.1484(3) 0.06941(18) 0.0215(5) Uani 1 1 d . . .
H12A H 1.266(6) 0.279(4) 0.088(3) 0.034(10) Uiso 1 1 d . . .
F13A F 1.5184(3) -0.17796(17) 0.11190(12) 0.0289(4) Uani 1 1 d . . .
H13A H 1.421(6) 0.199(3) 0.088(3) 0.027(10) Uiso 1 1 d . . .
C14A C 1.2366(5) -0.2317(2) 0.00604(19) 0.0237(6) Uani 1 1 d . . .
H14A H 1.310(12) 0.152(7) -0.029(5) 0.11(3) Uiso 1 1 d . . .
C15A C 1.0788(4) -0.1995(2) -0.03909(18) 0.0200(5) Uani 1 1 d . . .
H15A H 1.417(6) 0.030(3) 0.138(3) 0.030(10) Uiso 1 1 d . . .
C16A C 1.0409(4) -0.0868(2) -0.01817(16) 0.0158(5) Uani 1 1 d . . .
H16A H 1.265(7) -0.311(4) -0.010(3) 0.039(11) Uiso 1 1 d . . .
N17A N 0.8785(4) -0.05231(18) -0.06330(14) 0.0158(4) Uani 1 1 d . . .
H17A H 0.995(6) -0.248(3) -0.087(2) 0.024(9) Uiso 1 1 d . . .
C18A C 0.7087(4) -0.1428(2) -0.10473(17) 0.0169(5) Uani 1 1 d . . .
H18A H 0.662(8) -0.192(4) -0.063(3) 0.052(13) Uiso 1 1 d . . .
C19A C 0.5298(4) -0.0897(2) -0.13218(17) 0.0181(5) Uani 1 1 d . . .
H19A H 0.751(5) -0.193(3) -0.164(2) 0.015(7) Uiso 1 1 d . . .
N20A N 0.6014(4) -0.02048(19) -0.19271(14) 0.0175(4) Uani 1 1 d . . .
H20A H 0.474(7) -0.043(4) -0.074(3) 0.050 Uiso 1 1 d . . .
C21A C 0.7845(5) 0.0658(2) -0.15838(17) 0.0195(5) Uani 1 1 d . . .
H21A H 0.420(5) -0.144(3) -0.159(2) 0.017(8) Uiso 1 1 d . . .
C22A C 0.9557(4) 0.0101(2) -0.12899(17) 0.0187(5) Uani 1 1 d . . .
H22A H 0.723(6) 0.124(4) -0.118(3) 0.031(10) Uiso 1 1 d . . .
C23A C 0.4718(4) -0.0204(2) -0.26165(16) 0.0163(5) Uani 1 1 d . . .
H23A H 0.849(6) 0.098(3) -0.208(2) 0.020(8) Uiso 1 1 d . . .
O24A O 0.3120(3) -0.08628(17) -0.28452(12) 0.0207(4) Uani 1 1 d . . .
H24A H 1.086(5) 0.063(3) -0.1040(19) 0.006(6) Uiso 1 1 d . . .
O25A O 0.5495(3) 0.06183(17) -0.30162(13) 0.0230(4) Uani 1 1 d . . .
H25A H 1.017(7) -0.039(4) -0.181(3) 0.050 Uiso 1 1 d . . .
C26A C 0.4527(5) 0.0644(3) -0.38684(18) 0.0233(6) Uani 1 1 d . . .
H26A H 0.426(8) -0.037(5) -0.513(4) 0.063(15) Uiso 1 1 d . . .
C27A C 0.4842(6) -0.0428(3) -0.4572(2) 0.0280(6) Uani 1 1 d . . .
H27A H 0.628(6) -0.043(3) -0.460(2) 0.013(7) Uiso 1 1 d . . .
C28A C 0.5818(6) 0.1695(3) -0.4048(2) 0.0310(7) Uani 1 1 d . . .
H28A H 0.410(6) -0.106(4) -0.443(3) 0.031(10) Uiso 1 1 d . . .
C29A C 0.2238(6) 0.0784(3) -0.3779(2) 0.0334(7) Uani 1 1 d . . .
H29A H 0.545(9) 0.186(5) -0.455(4) 0.070(17) Uiso 1 1 d . . .
H30A H 0.732(6) 0.171(3) -0.403(2) 0.023(9) Uiso 1 1 d . . .
H31A H 0.565(5) 0.232(3) -0.361(2) 0.013(7) Uiso 1 1 d . . .
H32A H 0.208(5) 0.133(3) -0.333(2) 0.016(8) Uiso 1 1 d . . .
H33A H 0.143(6) 0.009(4) -0.375(3) 0.030(10) Uiso 1 1 d . . .
H34A H 0.175(6) 0.096(3) -0.431(3) 0.023(9) Uiso 1 1 d . . .
S1B S 1.22644(9) 0.50842(5) 0.31722(4) 0.01770(13) Uani 1 1 d . . .
H1B H 1.535(8) 0.697(4) 0.324(3) 0.050(13) Uiso 1 1 d . . .
O2B O 1.1172(3) 0.40394(17) 0.24997(15) 0.0258(4) Uani 1 1 d . . .
H2B H 1.320(10) 0.743(5) 0.375(5) 0.086(19) Uiso 1 1 d . . .
C3B C 1.2918(5) 0.6132(2) 0.25220(18) 0.0212(5) Uani 1 1 d . . .
H3B H 1.437(7) 0.784(4) 0.281(3) 0.040(11) Uiso 1 1 d . . .
C4B C 1.4121(7) 0.7207(3) 0.3144(2) 0.0326(7) Uani 1 1 d . . .
H4B H 1.007(6) 0.664(3) 0.268(3) 0.026(9) Uiso 1 1 d . . .
C5B C 1.0824(6) 0.6372(3) 0.2217(3) 0.0337(7) Uani 1 1 d . . .
H5B H 0.992(8) 0.575(4) 0.201(3) 0.045(13) Uiso 1 1 d . . .
C6B C 1.4180(7) 0.5647(3) 0.1731(2) 0.0315(7) Uani 1 1 d . . .
H6B H 1.092(6) 0.692(3) 0.193(2) 0.023(9) Uiso 1 1 d . . .
N7B N 1.4600(4) 0.4854(2) 0.34315(14) 0.0174(4) Uani 1 1 d . . .
H7B H 1.539(6) 0.559(3) 0.201(2) 0.013(7) Uiso 1 1 d . . .
C8B C 1.4897(4) 0.4658(2) 0.43211(16) 0.0181(5) Uani 1 1 d . . .
H8B H 1.368(7) 0.502(4) 0.139(3) 0.034(11) Uiso 1 1 d . . .
C9B C 1.6300(5) 0.3722(3) 0.4222(2) 0.0253(6) Uani 1 1 d . . .
H9B H 1.450(6) 0.631(3) 0.148(2) 0.022(8) Uiso 1 1 d . . .
C10B C 1.5932(4) 0.5753(2) 0.49752(16) 0.0168(5) Uani 1 1 d . . .
H10B H 1.543(6) 0.445(3) 0.300(2) 0.024(9) Uiso 1 1 d . . .
C11B C 1.7698(5) 0.6340(3) 0.47157(18) 0.0228(6) Uani 1 1 d . . .
H11B H 1.357(6) 0.448(3) 0.450(2) 0.017(8) Uiso 1 1 d . . .
C12B C 1.8688(5) 0.7334(3) 0.5276(2) 0.0271(6) Uani 1 1 d . . .
H12B H 1.550(7) 0.301(4) 0.381(3) 0.046(12) Uiso 1 1 d . . .
F13B F 2.0391(3) 0.79073(18) 0.49899(14) 0.0404(5) Uani 1 1 d . . .
H13B H 1.767(5) 0.400(3) 0.399(2) 0.013(7) Uiso 1 1 d . . .
C14B C 1.8014(5) 0.7770(3) 0.6115(2) 0.0273(6) Uani 1 1 d . . .
H14B H 1.650(6) 0.360(4) 0.476(3) 0.034(10) Uiso 1 1 d . . .
C15B C 1.6228(5) 0.7189(2) 0.63770(18) 0.0241(6) Uani 1 1 d . . .
H15B H 1.820(8) 0.600(4) 0.410(3) 0.052(13) Uiso 1 1 d . . .
C16B C 1.5173(4) 0.6168(2) 0.58259(16) 0.0188(5) Uani 1 1 d . . .
H16B H 1.879(6) 0.854(3) 0.650(3) 0.030(10) Uiso 1 1 d . . .
N17B N 1.3352(4) 0.5574(2) 0.61043(15) 0.0214(5) Uani 1 1 d . . .
H17B H 1.576(6) 0.751(3) 0.688(3) 0.026(9) Uiso 1 1 d . . .
C18B C 1.3666(6) 0.4532(3) 0.6329(2) 0.0316(7) Uani 1 1 d . . .
H18B H 1.463(7) 0.474(4) 0.702(3) 0.042(11) Uiso 1 1 d . . .
C19B C 1.1581(7) 0.3835(3) 0.6428(3) 0.0403(9) Uani 1 1 d . . .
H19B H 1.473(6) 0.416(4) 0.589(3) 0.033(10) Uiso 1 1 d . . .
N20B N 1.0371(5) 0.4530(3) 0.7080(2) 0.0368(7) Uani 1 1 d . . .
H20B H 1.186(6) 0.313(3) 0.668(2) 0.024(9) Uiso 1 1 d . . .
C21B C 1.0068(6) 0.5593(3) 0.6902(2) 0.0316(7) Uani 1 1 d . . .
H21B H 1.059(7) 0.372(4) 0.577(3) 0.046(12) Uiso 1 1 d . . .
C22B C 1.2187(6) 0.6263(3) 0.6803(2) 0.0276(6) Uani 1 1 d . . .
H22B H 0.944(6) 0.608(3) 0.740(3) 0.029(9) Uiso 1 1 d . . .
C23B C 0.9436(6) 0.4051(3) 0.7719(2) 0.0328(7) Uani 1 1 d . . .
H23B H 0.957(8) 0.541(4) 0.636(4) 0.050 Uiso 1 1 d . . .
O24B O 0.9669(5) 0.3125(2) 0.77988(18) 0.0385(6) Uani 1 1 d . . .
H24B H 1.308(7) 0.646(4) 0.742(3) 0.045(12) Uiso 1 1 d . . .
O25B O 0.8313(5) 0.4779(2) 0.82448(17) 0.0475(7) Uani 1 1 d . . .
H25B H 1.204(5) 0.697(3) 0.669(2) 0.015(8) Uiso 1 1 d . . .
C26B C 0.7122(8) 0.4429(3) 0.8966(3) 0.0526(12) Uani 1 1 d . . .
C27B C 0.8577(10) 0.4188(5) 0.9640(3) 0.0687(16) Uani 1 1 d . . .
H28B H 0.9224 0.3515 0.9359 0.103 Uiso 1 1 calc R . .
H26B H 0.7778 0.4048 1.0144 0.103 Uiso 1 1 calc R . .
H27B H 0.9668 0.4845 0.9852 0.103 Uiso 1 1 calc R . .
C28B C 0.6088(12) 0.5469(3) 0.9367(4) 0.085(2) Uani 1 1 d . . .
H29B H 0.7097 0.6052 0.9766 0.127 Uiso 1 1 calc R . .
H30B H 0.4891 0.5255 0.9704 0.127 Uiso 1 1 calc R . .
H31B H 0.5606 0.5773 0.8890 0.127 Uiso 1 1 calc R . .
C29B C 0.5475(7) 0.3411(3) 0.8561(3) 0.0419(9) Uani 1 1 d . . .
H32B H 0.4618 0.3592 0.8110 0.063 Uiso 1 1 calc R . .
H34B H 0.4583 0.3233 0.9029 0.063 Uiso 1 1 calc R . .
H33B H 0.6162 0.2752 0.8283 0.063 Uiso 1 1 calc R . .
O1C O 0.6960(4) 0.3537(2) 0.20550(15) 0.0276(5) Uani 1 1 d . . .
H1C H 0.693(7) 0.296(4) 0.211(3) 0.037(13) Uiso 1 1 d . . .
H2C H 0.839(6) 0.381(3) 0.212(2) 0.015(8) Uiso 1 1 d . . .
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
S1A O2A 1.504(2) . ?
S1A N7A 1.665(2) . ?
S1A C3A 1.844(3) . ?
C3A C6A 1.511(4) . ?
C3A C5A 1.523(5) . ?
C3A C4A 1.526(5) . ?
N7A C8A 1.491(3) . ?
C8A C9A 1.521(4) . ?
C8A C10A 1.528(4) . ?
C10A C11A 1.393(4) . ?
C10A C16A 1.409(3) . ?
C11A C12A 1.372(4) . ?
C12A F13A 1.364(3) . ?
C12A C14A 1.374(4) . ?
C14A C15A 1.394(4) . ?
C15A C16A 1.394(4) . ?
C16A N17A 1.431(3) . ?
N17A C18A 1.463(3) . ?
N17A C22A 1.478(3) . ?
C18A C19A 1.515(4) . ?
C19A N20A 1.461(3) . ?
N20A C23A 1.359(3) . ?
N20A C21A 1.471(3) . ?
C21A C22A 1.507(4) . ?
C23A O24A 1.210(3) . ?
C23A O25A 1.358(3) . ?
O25A C26A 1.474(3) . ?
C26A C29A 1.517(5) . ?
C26A C27A 1.518(5) . ?
C26A C28A 1.526(4) . ?
S1B O2B 1.513(2) . ?
S1B N7B 1.642(2) . ?
S1B C3B 1.839(3) . ?
C3B C6B 1.517(4) . ?
C3B C5B 1.525(5) . ?
C3B C4B 1.528(4) . ?
N7B C8B 1.482(3) . ?
C8B C10B 1.527(3) . ?
C8B C9B 1.539(4) . ?
C10B C11B 1.382(4) . ?
C10B C16B 1.407(3) . ?
C11B C12B 1.374(4) . ?
C12B F13B 1.362(4) . ?
C12B C14B 1.375(4) . ?
C14B C15B 1.391(4) . ?
C15B C16B 1.405(4) . ?
C16B N17B 1.425(4) . ?
N17B C18B 1.451(4) . ?
N17B C22B 1.475(4) . ?
C18B C19B 1.524(5) . ?
C19B N20B 1.454(4) . ?
N20B C23B 1.381(4) . ?
N20B C21B 1.441(5) . ?
C21B C22B 1.527(5) . ?
C23B O24B 1.205(4) . ?
C23B O25B 1.344(4) . ?
O25B C26B 1.483(4) . ?
C26B C28B 1.517(6) . ?
C26B C27B 1.518(8) . ?
C26B C29B 1.520(6) . ?
