#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/12/4021269.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_4021269
loop_
_publ_author_name
'Seiichiro Higashiya'
'Woo Jin Chung'
'Dong Sung Lim'
'Silvana C. Ngo'
'William H. Kelly IV'
'Paul J. Toscano'
'John T. Welch'
_publ_section_title
;
 Synthesis of Mono- and Difluoroacetyltrialkylsilanes
 and the Corresponding Enol Silyl Ethers
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6323
_journal_page_last               6328
_journal_paper_doi               10.1021/jo049551o
_journal_volume                  69
_journal_year                    2004
_chemical_formula_moiety         'C20 H17 F O Si'
_chemical_formula_sum            'C20 H17 F O Si'
_chemical_formula_weight         320.43
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.9305(12)
_cell_length_b                   7.2465(6)
_cell_length_c                   28.317(2)
_cell_measurement_temperature    173(2)
_cell_volume                     3268.9(4)
_diffrn_ambient_temperature      173(2)
_exptl_crystal_density_diffrn    1.302
_cod_database_code               4021269
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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
Si1 Si 0.76241(4) 0.56606(9) 0.14320(2) 0.01816(17) Uani 1 1 d . . .
F1 F 0.59565(12) 0.7864(3) 0.14628(9) 0.0462(5) Uani 1 1 d . . .
O1 O 0.74746(13) 0.7521(3) 0.05792(9) 0.0295(5) Uani 1 1 d . . .
C1 C 0.71021(16) 0.7233(4) 0.09527(9) 0.0219(5) Uani 1 1 d . . .
C2 C 0.6263(2) 0.8138(5) 0.10133(14) 0.0421(8) Uani 1 1 d . . .
H2A H 0.6316 0.9478 0.0952 0.051 Uiso 1 1 calc R . .
H2B H 0.5863 0.7622 0.0781 0.051 Uiso 1 1 calc R . .
C3 C 0.81581(16) 0.7323(3) 0.18407(9) 0.0192(5) Uani 1 1 d . . .
C4 C 0.90251(17) 0.7352(4) 0.18978(10) 0.0256(6) Uani 1 1 d . . .
H4 H 0.9356 0.6483 0.1729 0.031 Uiso 1 1 calc R . .
C5 C 0.94213(19) 0.8601(5) 0.21920(12) 0.0355(7) Uani 1 1 d . . .
H5 H 1.0015 0.8598 0.2221 0.043 Uiso 1 1 calc R . .
C6 C 0.8945(2) 0.9849(5) 0.24414(11) 0.0338(7) Uani 1 1 d . . .
H6 H 0.9212 1.0706 0.2646 0.041 Uiso 1 1 calc R . .
C7 C 0.80849(19) 0.9869(4) 0.23974(10) 0.0291(6) Uani 1 1 d . . .
H7 H 0.7761 1.0740 0.2570 0.035 Uiso 1 1 calc R . .
C8 C 0.76907(17) 0.8614(4) 0.21002(10) 0.0257(5) Uani 1 1 d . . .
H8 H 0.7096 0.8630 0.2072 0.031 Uiso 1 1 calc R . .
C9 C 0.83875(15) 0.4159(3) 0.11116(9) 0.0189(5) Uani 1 1 d . . .
C10 C 0.89882(15) 0.4910(4) 0.08027(10) 0.0227(5) Uani 1 1 d . . .
H10 H 0.9029 0.6210 0.0765 0.027 Uiso 1 1 calc R . .
C11 C 0.95237(17) 0.3750(4) 0.05519(10) 0.0280(6) Uani 1 1 d . . .
H11 H 0.9927 0.4272 0.0344 0.034 Uiso 1 1 calc R . .
C12 C 0.94799(18) 0.1852(4) 0.05991(11) 0.0296(6) Uani 1 1 d . . .
H12 H 0.9846 0.1078 0.0423 0.036 Uiso 1 1 calc R . .
C13 C 0.88981(19) 0.1098(4) 0.09047(12) 0.0326(7) Uani 1 1 d . . .
H13 H 0.8863 -0.0203 0.0941 0.039 Uiso 1 1 calc R . .
C14 C 0.83624(18) 0.2244(4) 0.11594(12) 0.0268(6) Uani 1 1 d . . .
H14 H 0.7970 0.1708 0.1371 0.032 Uiso 1 1 calc R . .
C15 C 0.68109(16) 0.4225(4) 0.17305(10) 0.0208(5) Uani 1 1 d . . .
C16 C 0.68102(17) 0.3969(4) 0.22161(10) 0.0259(5) Uani 1 1 d . . .
H16 H 0.7217 0.4580 0.2405 0.031 Uiso 1 1 calc R . .
C17 C 0.6209(2) 0.2810(5) 0.24309(13) 0.0332(7) Uani 1 1 d . . .
H17 H 0.6222 0.2620 0.2763 0.040 Uiso 1 1 calc R . .
C18 C 0.56127(19) 0.1963(4) 0.21647(12) 0.0314(6) Uani 1 1 d . . .
H18 H 0.5207 0.1190 0.2311 0.038 Uiso 1 1 calc R . .
C19 C 0.55980(19) 0.2227(5) 0.16838(12) 0.0309(6) Uani 1 1 d . . .
H19 H 0.5177 0.1645 0.1498 0.037 Uiso 1 1 calc R . .
C20 C 0.61904(17) 0.3332(4) 0.14696(10) 0.0271(6) Uani 1 1 d . . .
H20 H 0.6175 0.3490 0.1137 0.033 Uiso 1 1 calc R . .
Si1' Si 0.48836(4) 0.44878(9) 0.41834(2) 0.01811(17) Uani 1 1 d . . .
F1' F 0.65365(12) 0.2244(3) 0.41459(9) 0.0427(5) Uani 1 1 d . . .
O1' O 0.50811(13) 0.2811(3) 0.50575(9) 0.0333(5) Uani 1 1 d . . .
C1' C 0.54054(17) 0.3008(4) 0.46725(10) 0.0237(5) Uani 1 1 d . . .
C2' C 0.6228(2) 0.1954(5) 0.45971(12) 0.0381(8) Uani 1 1 d . . .
H2'1 H 0.6648 0.2369 0.4832 0.046 Uiso 1 1 calc R . .
H2'2 H 0.6130 0.0618 0.4646 0.046 Uiso 1 1 calc R . .
C3' C 0.41260(15) 0.6027(4) 0.44963(9) 0.0200(5) Uani 1 1 d . . .
C4' C 0.41565(17) 0.7924(4) 0.44350(11) 0.0265(6) Uani 1 1 d . . .
H4' H 0.4553 0.8435 0.4222 0.032 Uiso 1 1 calc R . .
C5' C 0.36091(19) 0.9113(4) 0.46834(12) 0.0299(6) Uani 1 1 d . . .
H5' H 0.3635 1.0408 0.4633 0.036 Uiso 1 1 calc R . .
C6' C 0.30321(17) 0.8390(4) 0.50022(11) 0.0280(6) Uani 1 1 d . . .
H6' H 0.2670 0.9181 0.5176 0.034 Uiso 1 1 calc R . .
C7' C 0.29943(17) 0.6491(4) 0.50624(11) 0.0254(5) Uani 1 1 d . . .
H7' H 0.2593 0.5984 0.5274 0.031 Uiso 1 1 calc R . .
C8' C 0.35298(17) 0.5318(4) 0.48194(10) 0.0239(5) Uani 1 1 d . . .
H8' H 0.3496 0.4025 0.4870 0.029 Uiso 1 1 calc R . .
C9' C 0.43597(16) 0.2795(4) 0.37749(9) 0.0206(5) Uani 1 1 d . . .
C10' C 0.48255(16) 0.1543(4) 0.35138(10) 0.0249(5) Uani 1 1 d . . .
H10' H 0.5420 0.1564 0.3536 0.030 Uiso 1 1 calc R . .
C11' C 0.4444(2) 0.0260(4) 0.32206(10) 0.0307(6) Uani 1 1 d . . .
H11' H 0.4778 -0.0579 0.3044 0.037 Uiso 1 1 calc R . .
C12' C 0.3570(2) 0.0200(4) 0.31855(10) 0.0312(6) Uani 1 1 d . . .
H12' H 0.3304 -0.0685 0.2988 0.037 Uiso 1 1 calc R . .
C13' C 0.30940(18) 0.1453(5) 0.34429(11) 0.0330(6) Uani 1 1 d . . .
H13' H 0.2499 0.1430 0.3417 0.040 Uiso 1 1 calc R . .
C14' C 0.34706(17) 0.2731(4) 0.37354(12) 0.0279(6) Uani 1 1 d . . .
H14' H 0.3135 0.3569 0.3911 0.034 Uiso 1 1 calc R . .
C15' C 0.56999(16) 0.5894(3) 0.38786(9) 0.0199(5) Uani 1 1 d . . .
C16' C 0.63186(18) 0.6787(4) 0.41450(11) 0.0282(6) Uani 1 1 d . . .
H16' H 0.6317 0.6659 0.4479 0.034 Uiso 1 1 calc R . .
C17' C 0.69322(19) 0.7852(5) 0.39322(13) 0.0328(7) Uani 1 1 d . . .
H17' H 0.7362 0.8399 0.4118 0.039 Uiso 1 1 calc R . .
C18' C 0.69196(18) 0.8120(4) 0.34449(11) 0.0302(6) Uani 1 1 d . . .
H18' H 0.7325 0.8894 0.3299 0.036 Uiso 1 1 calc R . .
C19' C 0.6317(2) 0.7258(5) 0.31760(11) 0.0316(6) Uani 1 1 d . . .
H19' H 0.6312 0.7424 0.2843 0.038 Uiso 1 1 calc R . .
C20' C 0.57141(17) 0.6141(4) 0.33898(10) 0.0264(5) Uani 1 1 d . . .
H20' H 0.5306 0.5539 0.3200 0.032 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
Si1 C15 1.864(3) . ?
Si1 C9 1.867(3) . ?
Si1 C3 1.875(3) . ?
Si1 C1 1.957(3) . ?
F1 C2 1.378(5) . ?
O1 C1 1.231(4) . ?
C1 C2 1.499(4) . ?
C3 C4 1.391(4) . ?
C3 C8 1.403(4) . ?
C4 C5 1.383(4) . ?
C5 C6 1.376(5) . ?
C6 C7 1.376(4) . ?
C7 C8 1.389(4) . ?
C9 C14 1.395(4) . ?
C9 C10 1.406(4) . ?
C10 C11 1.393(4) . ?
C11 C12 1.383(4) . ?
C12 C13 1.381(5) . ?
C13 C14 1.392(4) . ?
C15 C16 1.387(4) . ?
C15 C20 1.393(4) . ?
C16 C17 1.411(4) . ?
C17 C18 1.360(5) . ?
C18 C19 1.375(5) . ?
C19 C20 1.379(4) . ?
Si1' C15' 1.864(3) . ?
Si1' C3' 1.867(3) . ?
Si1' C9' 1.881(3) . ?
Si1' C1' 1.939(3) . ?
F1' C2' 1.385(4) . ?
O1' C1' 1.215(4) . ?
C1' C2' 1.532(4) . ?
C3' C4' 1.386(4) . ?
C3' C8' 1.415(4) . ?
C4' C5' 1.414(4) . ?
C5' C6' 1.391(4) . ?
C6' C7' 1.388(4) . ?
C7' C8' 1.387(4) . ?
C9' C10' 1.386(4) . ?
C9' C14' 1.422(4) . ?
C10' C11' 1.387(4) . ?
C11' C12' 1.397(5) . ?
C12' C13' 1.390(4) . ?
C13' C14' 1.379(4) . ?
C15' C20' 1.396(4) . ?
C15' C16' 1.400(4) . ?
C16' C17' 1.383(4) . ?
C17' C18' 1.394(5) . ?
C18' C19' 1.375(5) . ?
C19' C20' 1.394(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658508
