#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/04/4020438.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_4020438
loop_
_publ_author_name
'Kamal M. Dawood'
'Toshio Fuchigami'
_publ_section_title
;
 Electrolytic Partial Fluorination of Organic Compounds.
 Anodic Fluorination of Spiropyrazoline-5,3'-chroman-4-ones
 and Thiochromanone Analogues. A Route to Aroyl
 Fluoride Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7537
_journal_page_last               7541
_journal_paper_doi               10.1021/jo0507587
_journal_volume                  70
_journal_year                    2005
_chemical_formula_sum            'C29 H20 Cl F N2 O2'
_chemical_formula_weight         482.92
_chemical_name_common            'compound 6b'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 93.1640(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.1589(7)
_cell_length_b                   8.0433(2)
_cell_length_c                   18.0403(7)
_cell_measurement_temperature    213(2)
_cell_volume                     2341.14(15)
_diffrn_ambient_temperature      213(2)
_exptl_crystal_density_diffrn    1.370
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4020438
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
Cl1 Cl 0.33840(5) 0.15930(12) 0.77903(4) 0.0588(3) Uani 1 1 d . . .
F1 F -0.07280(14) 0.5931(2) 1.09487(17) 0.1077(10) Uani 1 1 d . . .
O1 O 0.05787(14) 0.5483(2) 1.09044(16) 0.0756(8) Uani 1 1 d . . .
O2 O 0.10627(10) 0.23081(19) 1.10233(10) 0.0328(4) Uani 1 1 d . . .
N1 N 0.26691(12) 0.2220(3) 1.22116(12) 0.0317(5) Uani 1 1 d . . .
N2 N 0.34746(12) 0.2670(3) 1.23200(12) 0.0335(5) Uani 1 1 d . . .
C1 C 0.37914(15) 0.2578(3) 1.16477(14) 0.0306(5) Uani 1 1 d . . .
C2 C 0.31740(14) 0.2093(3) 1.10992(14) 0.0274(5) Uani 1 1 d . . .
C3 C 0.24657(14) 0.1842(3) 1.14818(14) 0.0287(5) Uani 1 1 d . . .
C4 C 0.46799(15) 0.2954(3) 1.15978(14) 0.0298(5) Uani 1 1 d . . .
C5 C 0.50010(16) 0.3697(3) 1.09734(14) 0.0353(6) Uani 1 1 d . . .
C6 C 0.58410(16) 0.4064(3) 1.09620(15) 0.0399(6) Uani 1 1 d . . .
C7 C 0.63682(17) 0.3697(4) 1.15604(17) 0.0483(7) Uani 1 1 d . . .
C8 C 0.60581(18) 0.2947(5) 1.21761(19) 0.0597(9) Uani 1 1 d . . .
C9 C 0.52217(17) 0.2601(4) 1.21954(16) 0.0486(8) Uani 1 1 d . . .
C10 C 0.32243(14) 0.1901(3) 1.02884(14) 0.0268(5) Uani 1 1 d . . .
C11 C 0.26391(15) 0.2696(3) 0.98072(15) 0.0307(6) Uani 1 1 d . . .
C12 C 0.26823(15) 0.2588(3) 0.90416(15) 0.0332(6) Uani 1 1 d . . .
C13 C 0.33113(16) 0.1664(3) 0.87500(14) 0.0359(6) Uani 1 1 d . . .
C14 C 0.38797(15) 0.0825(3) 0.92059(15) 0.0352(6) Uani 1 1 d . . .
C15 C 0.38422(14) 0.0965(3) 0.99695(14) 0.0322(6) Uani 1 1 d . . .
C16 C 0.16634(14) 0.1045(3) 1.12388(15) 0.0313(6) Uani 1 1 d . . .
C17 C 0.02498(14) 0.1866(3) 1.09597(14) 0.0296(5) Uani 1 1 d . . .
C18 C -0.00242(16) 0.0222(3) 1.09562(18) 0.0438(7) Uani 1 1 d . . .
C19 C -0.08577(18) -0.0114(3) 1.0882(2) 0.0573(9) Uani 1 1 d . . .
C20 C -0.14445(16) 0.1129(4) 1.0817(2) 0.0531(8) Uani 1 1 d . . .
C21 C -0.11848(16) 0.2744(3) 1.08257(18) 0.0434(7) Uani 1 1 d . . .
C22 C -0.03426(15) 0.3143(3) 1.09023(14) 0.0315(6) Uani 1 1 d . . .
C23 C -0.00986(19) 0.4900(3) 1.09157(18) 0.0477(8) Uani 1 1 d . . .
C24 C 0.21492(15) 0.2254(3) 1.28274(14) 0.0318(6) Uani 1 1 d . . .
C25 C 0.24529(17) 0.1674(3) 1.35099(16) 0.0416(7) Uani 1 1 d . . .
C26 C 0.1941(2) 0.1725(3) 1.41013(17) 0.0479(7) Uani 1 1 d . . .
C27 C 0.1140(2) 0.2313(3) 1.40146(17) 0.0487(8) Uani 1 1 d . . .
C28 C 0.08484(18) 0.2902(4) 1.33336(19) 0.0518(8) Uani 1 1 d . . .
C29 C 0.13568(18) 0.2904(4) 1.27380(16) 0.0447(7) Uani 1 1 d . . .
H1 H 0.4629 0.3932 1.0545 0.040 Uiso 1 1 d . . .
H2 H 0.6052 0.4599 1.0528 0.049 Uiso 1 1 d . . .
H3 H 0.6953 0.3974 1.1552 0.056 Uiso 1 1 d . . .
H4 H 0.6426 0.2635 1.2588 0.073 Uiso 1 1 d . . .
H5 H 0.5009 0.2081 1.2623 0.058 Uiso 1 1 d . . .
H6 H 0.2209 0.3324 1.0017 0.038 Uiso 1 1 d . . .
H7 H 0.2282 0.3154 0.8715 0.040 Uiso 1 1 d . . .
H8 H 0.4301 0.0155 0.8999 0.042 Uiso 1 1 d . . .
H9 H 0.4250 0.0409 1.0292 0.040 Uiso 1 1 d . . .
H10 H 0.1464 0.0401 1.1639 0.038 Uiso 1 1 d . . .
H11 H 0.1745 0.0318 1.0831 0.038 Uiso 1 1 d . . .
H12 H 0.0372 -0.0680 1.0990 0.053 Uiso 1 1 d . . .
H13 H -0.1047 -0.1247 1.0882 0.065 Uiso 1 1 d . . .
H14 H -0.2020 0.0862 1.0769 0.062 Uiso 1 1 d . . .
H15 H -0.1581 0.3626 1.0783 0.052 Uiso 1 1 d . . .
H16 H 0.3011 0.1244 1.3572 0.051 Uiso 1 1 d . . .
H17 H 0.2148 0.1353 1.4588 0.058 Uiso 1 1 d . . .
H18 H 0.0782 0.2321 1.4427 0.061 Uiso 1 1 d . . .
H19 H 0.0279 0.3299 1.3260 0.063 Uiso 1 1 d . . .
H20 H 0.1167 0.3372 1.2269 0.053 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
Cl1 C13 1.743(3) . ?
F1 C23 1.316(3) . ?
O1 C23 1.192(3) . ?
O2 C17 1.360(3) . ?
O2 C16 1.443(3) . ?
N1 N2 1.355(3) . ?
N1 C3 1.373(3) . ?
N1 C24 1.430(3) . ?
N2 C1 1.344(3) . ?
C1 C2 1.420(3) . ?
C1 C4 1.475(3) . ?
C2 C3 1.384(3) . ?
C2 C10 1.478(3) . ?
C3 C16 1.490(3) . ?
C4 C9 1.380(4) . ?
C4 C5 1.400(3) . ?
C5 C6 1.390(4) . ?
C6 C7 1.370(4) . ?
C7 C8 1.382(4) . ?
C8 C9 1.382(4) . ?
C10 C15 1.399(3) . ?
C10 C11 1.402(3) . ?
C11 C12 1.389(4) . ?
C12 C13 1.386(4) . ?
C13 C14 1.375(4) . ?
C14 C15 1.387(4) . ?
C17 C18 1.395(3) . ?
C17 C22 1.404(3) . ?
C18 C19 1.373(4) . ?
C19 C20 1.379(4) . ?
C20 C21 1.365(4) . ?
C21 C22 1.398(4) . ?
C22 C23 1.467(4) . ?
C24 C25 1.381(4) . ?
C24 C29 1.384(4) . ?
C25 C26 1.386(4) . ?
C26 C27 1.379(4) . ?
C27 C28 1.375(4) . ?
C28 C29 1.388(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9873435
