#------------------------------------------------------------------------------
#$Date: 2022-09-14 23:33:16 +0300 (Wed, 14 Sep 2022) $
#$Revision: 277842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/06/4020634.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_4020634
loop_
_publ_author_name
'Aurelie Baron'
'Graham Sandford'
'Rachel Slater'
'Dmitry S. Yufit'
'Judith A. K. Howard'
'Antonio Vong'
_publ_section_title
;
 Polyfunctional Tetrahydropyrido[2,3-b]pyrazine Scaffolds
 from 4-Phenylsulfonyl Tetrafluoropyridine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9377
_journal_page_last               9381
_journal_paper_doi               10.1021/jo051453v
_journal_volume                  70
_journal_year                    2005
_chemical_formula_moiety         'C14 H13 F2 N3 O2 S'
_chemical_formula_sum            'C14 H13 F2 N3 O2 S'
_chemical_formula_weight         325.33
_chemical_melting_point          180.0(10)
_space_group_IT_number           2
_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                105.942(2)
_cell_angle_beta                 103.247(2)
_cell_angle_gamma                105.640(2)
_cell_formula_units_Z            4
_cell_length_a                   10.1943(5)
_cell_length_b                   10.5803(6)
_cell_length_c                   14.7937(8)
_cell_measurement_temperature    120(2)
_cell_volume                     1396.00(13)
_diffrn_ambient_temperature      120(2)
_exptl_crystal_density_diffrn    1.548
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '179.0-181.0' was changed to
'180.0(10)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4020634
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
S1 S 0.83699(5) 0.64592(5) 0.32880(3) 0.02210(12) Uani 1 1 d . A .
F6 F 0.54390(13) 0.84620(12) 0.12003(9) 0.0343(3) Uani 1 1 d . . .
F7 F 0.78235(12) 0.87233(11) 0.25944(8) 0.0312(3) Uani 1 1 d . . .
O1 O 0.96263(13) 0.74858(15) 0.33039(10) 0.0303(3) Uani 1 1 d . . .
O2 O 0.83975(14) 0.50725(14) 0.31849(10) 0.0291(3) Uani 1 1 d . . .
N1 N 0.56062(18) 0.37393(17) 0.19585(13) 0.0276(4) Uani 1 1 d . . .
H1N H 0.638(3) 0.375(2) 0.2366(17) 0.044(7) Uiso 1 1 d . . .
N4 N 0.33004(18) 0.38064(17) 0.06190(12) 0.0305(4) Uani 1 1 d . A .
H4N H 0.2563 0.3828 0.0184 0.037 Uiso 1 1 calc R . .
N5 N 0.44436(17) 0.61482(17) 0.09135(11) 0.0252(4) Uani 1 1 d . A .
C2 C 0.4146(4) 0.2612(4) 0.1685(3) 0.0191(7) Uiso 0.50 1 d P A 1
H2A H 0.3721 0.2896 0.2219 0.023 Uiso 0.50 1 calc PR A 1
C2A C 0.4657(4) 0.2465(4) 0.1263(3) 0.0322(9) Uiso 0.50 1 d P A 2
H2AA H 0.5087 0.2201 0.0728 0.039 Uiso 0.50 1 calc PR A 2
C3 C 0.3208(2) 0.2515(2) 0.07757(19) 0.0406(6) Uani 1 1 d . . .
H3B H 0.2991 0.2788 0.1384 0.049 Uiso 0.50 1 d P B 2
H3A H 0.3740 0.2214 0.0357 0.049 Uiso 0.50 1 d P C 1
H31 H 0.232(2) 0.182(2) 0.0460(17) 0.040 Uiso 1 1 d . . .
C6 C 0.5562(2) 0.7324(2) 0.14090(14) 0.0249(4) Uani 1 1 d . . .
C7 C 0.67662(19) 0.74561(19) 0.21033(13) 0.0221(4) Uani 1 1 d . A .
C8 C 0.68544(18) 0.62610(19) 0.23219(13) 0.0201(4) Uani 1 1 d . . .
C9 C 0.56965(19) 0.49924(19) 0.18209(13) 0.0219(4) Uani 1 1 d . A .
C10 C 0.4473(2) 0.4997(2) 0.11106(13) 0.0234(4) Uani 1 1 d . . .
C11 C 0.79595(18) 0.71319(19) 0.43800(13) 0.0207(4) Uani 1 1 d . . .
C12 C 0.8874(2) 0.8411(2) 0.50832(15) 0.0335(5) Uani 1 1 d . A .
H12 H 0.9724 0.8918 0.4990 0.040 Uiso 1 1 calc R . .
C13 C 0.8542(3) 0.8959(2) 0.59347(16) 0.0391(5) Uani 1 1 d . . .
H13 H 0.9161 0.9845 0.6426 0.047 Uiso 1 1 calc R A .
C14 C 0.7319(2) 0.8214(2) 0.60601(14) 0.0324(5) Uani 1 1 d . A .
H14 H 0.7083 0.8597 0.6635 0.039 Uiso 1 1 calc R . .
C15 C 0.6424(2) 0.6915(2) 0.53650(15) 0.0323(5) Uani 1 1 d . . .
H15 H 0.5588 0.6400 0.5469 0.039 Uiso 1 1 calc R A .
C16 C 0.6739(2) 0.6360(2) 0.45171(14) 0.0275(4) Uani 1 1 d . A .
H16 H 0.6128 0.5463 0.4035 0.033 Uiso 1 1 calc R . .
C17 C 0.4450(3) 0.1296(2) 0.17078(19) 0.0392(5) Uani 1 1 d . . .
S2 S 0.32112(5) 0.64197(5) 0.31849(3) 0.02396(13) Uani 1 1 d . D .
F26 F 0.01989(13) 0.84105(12) 0.11447(9) 0.0361(3) Uani 1 1 d . . .
F27 F 0.26327(12) 0.86703(11) 0.24930(9) 0.0337(3) Uani 1 1 d . . .
O21 O 0.44566(14) 0.74128(15) 0.31563(10) 0.0333(3) Uani 1 1 d . . .
O22 O 0.32187(14) 0.50418(14) 0.31331(10) 0.0316(3) Uani 1 1 d . . .
N21 N 0.04672(18) 0.36738(17) 0.18413(13) 0.0275(4) Uani 1 1 d . . .
H21N H 0.125(2) 0.372(2) 0.2306(17) 0.038(6) Uiso 1 1 d . . .
N24 N -0.18665(18) 0.37355(17) 0.05299(12) 0.0306(4) Uani 1 1 d . D .
H24N H -0.2610 0.3751 0.0097 0.037 Uiso 1 1 calc R . .
N25 N -0.07689(17) 0.60879(17) 0.08490(11) 0.0256(3) Uani 1 1 d . D .
C22 C -0.0993(4) 0.2551(3) 0.1579(2) 0.0162(6) Uiso 0.50 1 d P D 1
H22A H -0.1408 0.2844 0.2118 0.019 Uiso 0.50 1 calc PR D 1
C22A C -0.0504(5) 0.2398(5) 0.1190(3) 0.0345(9) Uiso 0.50 1 d P D 2
H22B H -0.0088 0.2122 0.0649 0.041 Uiso 0.50 1 calc PR D 2
C23 C -0.1936(2) 0.2449(2) 0.0681(2) 0.0404(6) Uani 1 1 d . . .
H23B H -0.2146 0.2729 0.1291 0.049 Uiso 0.50 1 d P E 2
H23A H -0.1420 0.2142 0.0250 0.049 Uiso 0.50 1 d P F 1
H231 H -0.274(2) 0.177(2) 0.0412(17) 0.040 Uiso 1 1 d . . .
C26 C 0.0350(2) 0.7269(2) 0.13363(14) 0.0256(4) Uani 1 1 d . . .
C27 C 0.1573(2) 0.73963(19) 0.20059(14) 0.0240(4) Uani 1 1 d . D .
C28 C 0.16780(19) 0.6198(2) 0.22128(13) 0.0224(4) Uani 1 1 d . . .
C29 C 0.05278(19) 0.49242(19) 0.17190(13) 0.0214(4) Uani 1 1 d . D .
C30 C -0.0711(2) 0.4929(2) 0.10228(13) 0.0230(4) Uani 1 1 d . . .
C31 C 0.28488(18) 0.7170(2) 0.42779(13) 0.0225(4) Uani 1 1 d . . .
C32 C 0.3349(2) 0.8620(2) 0.47156(15) 0.0313(4) Uani 1 1 d . D .
H32 H 0.3854 0.9196 0.4423 0.038 Uiso 1 1 calc R . .
C33 C 0.3097(2) 0.9219(2) 0.55948(16) 0.0371(5) Uani 1 1 d . . .
H33 H 0.3448 1.0212 0.5916 0.045 Uiso 1 1 calc R D .
C34 C 0.2331(2) 0.8358(2) 0.59947(15) 0.0339(5) Uani 1 1 d . D .
H34 H 0.2172 0.8764 0.6599 0.041 Uiso 1 1 calc R . .
C35 C 0.1797(2) 0.6919(2) 0.55274(15) 0.0365(5) Uani 1 1 d . . .
H35 H 0.1246 0.6343 0.5799 0.044 Uiso 1 1 calc R D .
C36 C 0.2057(2) 0.6306(2) 0.46627(14) 0.0289(4) Uani 1 1 d . D .
H36 H 0.1698 0.5313 0.4341 0.035 Uiso 1 1 calc R . .
C37 C -0.0688(3) 0.1228(2) 0.16042(19) 0.0375(5) Uani 1 1 d . . .
H371 H -0.005(2) 0.136(2) 0.2227(18) 0.040 Uiso 1 1 d . . .
H171 H 0.489(2) 0.138(2) 0.2330(18) 0.040 Uiso 1 1 d . . .
H172 H 0.363(3) 0.054(3) 0.1478(17) 0.040 Uiso 1 1 d . . .
H173 H 0.483(3) 0.092(3) 0.1311(17) 0.040 Uiso 1 1 d . . .
H372 H -0.154(3) 0.052(2) 0.1430(17) 0.040 Uiso 1 1 d . . .
H373 H 0.000(2) 0.101(2) 0.1298(16) 0.040 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
S1 O1 1.4292(14) . ?
S1 O2 1.4416(13) . ?
S1 C8 1.7669(17) . ?
S1 C11 1.7692(18) . ?
F6 C6 1.3526(19) . ?
F7 C7 1.347(2) . ?
N1 C2A 1.375(4) . ?
N1 C9 1.378(2) . ?
N1 C2 1.518(4) . ?
N4 C10 1.353(2) . ?
N4 C3 1.429(3) . ?
N5 C6 1.318(2) . ?
N5 C10 1.334(2) . ?
C2 C3 1.420(4) . ?
C2 C17 1.513(4) . ?
C2A C3 1.510(4) . ?
C2A C17 1.542(5) . ?
C6 C7 1.353(2) . ?
C7 C8 1.409(2) . ?
C8 C9 1.394(3) . ?
C9 C10 1.437(2) . ?
C11 C12 1.373(3) . ?
C11 C16 1.384(2) . ?
C12 C13 1.392(3) . ?
C13 C14 1.366(3) . ?
C14 C15 1.377(3) . ?
C15 C16 1.380(3) . ?
S2 O21 1.4309(14) . ?
S2 O22 1.4409(14) . ?
S2 C31 1.7630(18) . ?
S2 C28 1.7758(18) . ?
F26 C26 1.353(2) . ?
F27 C27 1.352(2) . ?
N21 C22A 1.363(4) . ?
N21 C29 1.371(2) . ?
N21 C22 1.518(4) . ?
N24 C30 1.346(2) . ?
N24 C23 1.425(3) . ?
N25 C26 1.320(2) . ?
N25 C30 1.334(2) . ?
C22 C23 1.408(4) . ?
C22 C37 1.521(4) . ?
C22A C23 1.504(5) . ?
C22A C37 1.512(5) . ?
C26 C27 1.350(3) . ?
C27 C28 1.408(2) . ?
C28 C29 1.393(3) . ?
C29 C30 1.437(2) . ?
C31 C36 1.382(3) . ?
C31 C32 1.383(3) . ?
C32 C33 1.396(3) . ?
C33 C34 1.383(3) . ?
C34 C35 1.376(3) . ?
C35 C36 1.385(3) . ?
