#------------------------------------------------------------------------------
#$Date: 2022-09-14 23:33:16 +0300 (Wed, 14 Sep 2022) $
#$Revision: 277842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/06/4020631.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_4020631
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         'C25 H19 F2 N3 O2 S'
_chemical_formula_sum            'C25 H19 F2 N3 O2 S'
_chemical_formula_weight         463.49
_chemical_melting_point          186.2(8)
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.7318(4)
_cell_length_b                   9.9214(2)
_cell_length_c                   23.5820(5)
_cell_measurement_temperature    120(2)
_cell_volume                     4382.61(16)
_diffrn_ambient_temperature      120(2)
_exptl_crystal_density_diffrn    1.405
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '185.4-186.9' was changed to
'186.2(8)' - 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               4020631
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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
S1 S 0.159999(16) 1.03307(3) 0.453703(13) 0.02335(9) Uani 1 1 d . . .
F6 F 0.01271(4) 0.77955(9) 0.59931(3) 0.03085(19) Uani 1 1 d . . .
F7 F 0.08218(4) 1.00358(9) 0.56230(3) 0.0324(2) Uani 1 1 d . . .
O1 O 0.12061(5) 1.15520(10) 0.46265(4) 0.0306(2) Uani 1 1 d . . .
O2 O 0.18876(5) 1.00586(11) 0.39813(4) 0.0311(2) Uani 1 1 d . . .
N1 N 0.12110(6) 0.76453(12) 0.38436(5) 0.0254(2) Uani 1 1 d . . .
N4 N 0.04158(6) 0.56059(12) 0.43129(5) 0.0271(2) Uani 1 1 d . . .
N5 N 0.02885(5) 0.67563(11) 0.51512(4) 0.0236(2) Uani 1 1 d . . .
C2 C 0.13060(7) 0.62740(14) 0.36279(5) 0.0237(3) Uani 1 1 d . . .
C3 C 0.05945(7) 0.55023(14) 0.37151(5) 0.0236(3) Uani 1 1 d . . .
C6 C 0.03941(6) 0.78415(14) 0.54624(5) 0.0237(3) Uani 1 1 d . . .
C7 C 0.07521(7) 0.89491(14) 0.52823(5) 0.0244(3) Uani 1 1 d . . .
C8 C 0.10623(6) 0.89370(13) 0.47339(5) 0.0226(2) Uani 1 1 d . . .
C9 C 0.09665(6) 0.78062(13) 0.43903(5) 0.0222(2) Uani 1 1 d . . .
C10 C 0.05483(6) 0.67185(13) 0.46243(5) 0.0224(2) Uani 1 1 d . . .
C11 C 0.23138(7) 1.02819(13) 0.50254(5) 0.0230(3) Uani 1 1 d . . .
C12 C 0.22864(7) 1.11114(14) 0.54985(6) 0.0264(3) Uani 1 1 d . . .
C13 C 0.28433(8) 1.10602(16) 0.58865(6) 0.0316(3) Uani 1 1 d . . .
C14 C 0.34104(8) 1.01918(16) 0.58016(7) 0.0334(3) Uani 1 1 d . . .
C15 C 0.34371(7) 0.93761(15) 0.53268(7) 0.0324(3) Uani 1 1 d . . .
C16 C 0.28832(7) 0.94076(14) 0.49317(7) 0.0283(3) Uani 1 1 d . . .
C17 C 0.15445(7) 0.62843(14) 0.30171(5) 0.0236(3) Uani 1 1 d . . .
C18 C 0.20494(7) 0.53509(15) 0.28384(6) 0.0292(3) Uani 1 1 d . . .
C19 C 0.22399(8) 0.52677(17) 0.22699(7) 0.0340(3) Uani 1 1 d . . .
C20 C 0.19224(8) 0.61073(16) 0.18769(6) 0.0328(3) Uani 1 1 d . . .
C21 C 0.14247(8) 0.70561(15) 0.20524(6) 0.0306(3) Uani 1 1 d . . .
C22 C 0.12385(7) 0.71491(14) 0.26208(6) 0.0271(3) Uani 1 1 d . . .
C23 C -0.00053(7) 0.59815(14) 0.33290(6) 0.0259(3) Uani 1 1 d . . .
C24 C -0.01470(9) 0.52905(16) 0.28288(7) 0.0351(3) Uani 1 1 d . . .
C25 C -0.06677(11) 0.5766(2) 0.24552(8) 0.0500(5) Uani 1 1 d . . .
C26 C -0.10525(10) 0.6916(2) 0.25847(9) 0.0525(5) Uani 1 1 d . . .
C27 C -0.09212(9) 0.75957(19) 0.30837(8) 0.0443(4) Uani 1 1 d . . .
C28 C -0.04003(7) 0.71370(16) 0.34562(7) 0.0327(3) Uani 1 1 d . . .
H1N H 0.1507(10) 0.8235(19) 0.3728(8) 0.036(5) Uiso 1 1 d . . .
H4N H 0.0205(11) 0.4906(19) 0.4484(8) 0.045(5) Uiso 1 1 d . . .
H2 H 0.1679(8) 0.5773(16) 0.3854(7) 0.024(4) Uiso 1 1 d . . .
H3 H 0.0687(8) 0.4561(16) 0.3641(6) 0.024(4) Uiso 1 1 d . . .
H12 H 0.1904(9) 1.1710(17) 0.5553(7) 0.026(4) Uiso 1 1 d . . .
H13 H 0.2817(9) 1.1634(18) 0.6219(7) 0.034(4) Uiso 1 1 d . . .
H14 H 0.3781(10) 1.0159(19) 0.6073(8) 0.040(5) Uiso 1 1 d . . .
H15 H 0.3835(11) 0.878(2) 0.5248(8) 0.049(5) Uiso 1 1 d . . .
H16 H 0.2877(8) 0.8833(17) 0.4612(7) 0.030(4) Uiso 1 1 d . . .
H18 H 0.2259(9) 0.4739(18) 0.3116(7) 0.036(5) Uiso 1 1 d . . .
H19 H 0.2601(11) 0.461(2) 0.2160(8) 0.050(5) Uiso 1 1 d . . .
H20 H 0.2023(9) 0.6041(18) 0.1487(8) 0.039(5) Uiso 1 1 d . . .
H21 H 0.1193(9) 0.7667(18) 0.1779(7) 0.034(4) Uiso 1 1 d . . .
H22 H 0.0877(9) 0.7760(18) 0.2744(8) 0.036(4) Uiso 1 1 d . . .
H24 H 0.0121(9) 0.4556(17) 0.2739(7) 0.027(4) Uiso 1 1 d . . .
H25 H -0.0727(12) 0.527(2) 0.2093(10) 0.063(6) Uiso 1 1 d . . .
H26 H -0.1416(12) 0.726(2) 0.2325(10) 0.063(6) Uiso 1 1 d . . .
H27 H -0.1188(11) 0.839(2) 0.3185(9) 0.052(6) Uiso 1 1 d . . .
H28 H -0.0329(9) 0.7632(18) 0.3804(8) 0.036(5) 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 1.4343(10) . ?
S1 O2 1.4424(10) . ?
S1 C11 1.7653(13) . ?
S1 C8 1.7726(13) . ?
F6 C6 1.3485(14) . ?
F7 C7 1.3509(15) . ?
N1 C9 1.3774(16) . ?
N1 C2 1.4633(18) . ?
N1 H1N 0.852(19) . ?
N4 C10 1.3488(17) . ?
N4 C3 1.4527(16) . ?
N4 H4N 0.90(2) . ?
N5 C6 1.3180(17) . ?
N5 C10 1.3350(16) . ?
C2 C17 1.5081(17) . ?
C2 C3 1.5508(18) . ?
C2 H2 1.009(16) . ?
C3 C23 1.5222(19) . ?
C3 H3 0.965(16) . ?
C6 C7 1.3556(19) . ?
C7 C8 1.4179(17) . ?
C8 C9 1.3955(18) . ?
C9 C10 1.4433(17) . ?
C11 C12 1.3873(19) . ?
C11 C16 1.3925(19) . ?
C12 C13 1.3886(19) . ?
C12 H12 0.940(16) . ?
C13 C14 1.382(2) . ?
C13 H13 0.970(18) . ?
C14 C15 1.383(2) . ?
C14 H14 0.944(19) . ?
C15 C16 1.395(2) . ?
C15 H15 0.97(2) . ?
C16 H16 0.945(17) . ?
C17 C18 1.3891(19) . ?
C17 C22 1.3921(19) . ?
C18 C19 1.390(2) . ?
C18 H18 0.975(18) . ?
C19 C20 1.381(2) . ?
C19 H19 0.97(2) . ?
C20 C21 1.388(2) . ?
C20 H20 0.941(18) . ?
C21 C22 1.3881(19) . ?
C21 H21 0.985(17) . ?
C22 H22 0.954(18) . ?
C23 C24 1.390(2) . ?
C23 C28 1.397(2) . ?
C24 C25 1.396(2) . ?
C24 H24 0.910(17) . ?
C25 C26 1.384(3) . ?
C25 H25 0.99(2) . ?
C26 C27 1.379(3) . ?
C26 H26 0.98(2) . ?
C27 C28 1.390(2) . ?
C27 H27 0.96(2) . ?
C28 H28 0.965(18) . ?
