#------------------------------------------------------------------------------
#$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013773.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_2013773
loop_
_publ_author_name
'Choudhury, A. R'
'Nagarajan, K.'
'Guru Row, T. N.'
_publ_section_title
;
An analysis of C-H...O and C-H...\p interactions in three substituted
4-ketotetrahydroindoles
;
_journal_name_full               'Acta Crystallographica, Section C'
_journal_page_first              o219
_journal_page_last               o222
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C23 H22 F N O2'
_chemical_formula_moiety         'C23 H22 F N O2'
_chemical_formula_sum            'C23 H22 F N O2'
_chemical_formula_weight         363.42
_chemical_melting_point          494
_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
_cell_angle_beta                 116.348(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.112(2)
_cell_length_b                   19.073(4)
_cell_length_c                   11.287(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1950.8(8)
_diffrn_ambient_temperature      273(2)
_exptl_crystal_density_diffrn    1.237
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_database_code               2013773
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,1/2-z
-x,-y,-z
1/2+x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
F1 0.25458(15) 0.35840(6) 0.68136(15) 0.1001(5) Uani d . 1 . . F
O1 0.81733(13) -0.04919(6) 0.59350(12) 0.0591(3) Uani d . 1 . . O
O2 0.74360(13) 0.41255(7) 0.27699(13) 0.0692(4) Uani d . 1 . . O
N1 0.58615(13) 0.15763(6) 0.58559(12) 0.0422(3) Uani d . 1 . . N
C1 0.66762(15) 0.16589(8) 0.51285(15) 0.0421(3) Uani d . 1 . . C
C2 0.73415(17) 0.10389(8) 0.51610(15) 0.0439(4) Uani d . 1 . . C
C3 0.73646(16) -0.01635(8) 0.62834(15) 0.0438(4) Uani d . 1 . . C
C4 0.6681(2) -0.05015(9) 0.70871(18) 0.0511(4) Uani d . 1 . . C
C5 0.63399(19) -0.00126(9) 0.79896(16) 0.0539(4) Uani d . 1 . . C
C6 0.5407(2) 0.06088(9) 0.71829(18) 0.0519(4) Uani d . 1 . . C
C7 0.60495(16) 0.09075(7) 0.63381(14) 0.0417(3) Uani d . 1 . . C
C8 0.69592(15) 0.05605(8) 0.59254(14) 0.0419(3) Uani d . 1 . . C
C9 0.50004(16) 0.21030(7) 0.61026(15) 0.0419(3) Uani d . 1 . . C
C10 0.56745(19) 0.26830(9) 0.68513(18) 0.0548(4) Uani d . 1 . . C
C11 0.4849(2) 0.31890(9) 0.7094(2) 0.0643(5) Uani d . 1 . . C
C12 0.3365(2) 0.30926(9) 0.6576(2) 0.0625(5) Uani d . 1 . . C
C13 0.2667(2) 0.25201(10) 0.5838(2) 0.0642(5) Uani d . 1 . . C
C14 0.34993(18) 0.20199(9) 0.55971(18) 0.0522(4) Uani d . 1 . . C
C15 0.67816(16) 0.23226(8) 0.45051(14) 0.0427(4) Uani d . 1 . . C
C16 0.81536(18) 0.25265(9) 0.46274(18) 0.0529(4) Uani d . 1 . . C
C17 0.83263(19) 0.31212(9) 0.40332(18) 0.0573(4) Uani d . 1 . . C
C18 0.71305(17) 0.35407(8) 0.32950(15) 0.0473(4) Uani d . 1 . . C
C19 0.57575(19) 0.33536(9) 0.31572(17) 0.0543(4) Uani d . 1 . . C
C20 0.55954(18) 0.27460(9) 0.37593(18) 0.0555(4) Uani d . 1 . . C
C21 0.5437(4) -0.04221(14) 0.8545(3) 0.0829(7) Uani d . 1 . . C
C22 0.7775(3) 0.02470(16) 0.9109(2) 0.0837(7) Uani d . 1 . . C
C23 0.6276(3) 0.45901(14) 0.2033(3) 0.0835(7) Uani d . 1 . . C
H2 0.7935(17) 0.0944(8) 0.4719(14) 0.045(4) Uiso d . 1 . . H
H4A 0.7330(19) -0.0871(9) 0.7600(16) 0.059(5) Uiso d . 1 . . H
H4B 0.575(2) -0.0728(9) 0.6444(17) 0.060(5) Uiso d . 1 . . H
H6A 0.532(2) 0.0967(10) 0.7770(18) 0.067(5) Uiso d . 1 . . H
H6B 0.437(2) 0.0456(9) 0.6609(17) 0.061(5) Uiso d . 1 . . H
H10 0.674(2) 0.2724(9) 0.7212(17) 0.068(5) Uiso d . 1 . . H
H11 0.529(2) 0.3602(11) 0.762(2) 0.078(6) Uiso d . 1 . . H
H13 0.161(2) 0.2480(10) 0.5496(18) 0.077(6) Uiso d . 1 . . H
H14 0.3025(17) 0.1611(9) 0.5099(16) 0.052(4) Uiso d . 1 . . H
H16 0.901(2) 0.2242(10) 0.5145(17) 0.066(5) Uiso d . 1 . . H
H17 0.930(2) 0.3261(10) 0.4126(18) 0.071(5) Uiso d . 1 . . H
H19 0.489(2) 0.3630(9) 0.2640(17) 0.065(5) Uiso d . 1 . . H
H20 0.462(2) 0.2606(9) 0.3635(17) 0.066(5) Uiso d . 1 . . H
H21A 0.838(2) 0.0544(12) 0.882(2) 0.094(7) Uiso d . 1 . . H
H21B 0.840(3) -0.0166(14) 0.959(3) 0.113(9) Uiso d . 1 . . H
H21C 0.758(3) 0.0566(13) 0.970(3) 0.116(9) Uiso d . 1 . . H
H22A 0.604(2) -0.0790(13) 0.910(2) 0.096(7) Uiso d . 1 . . H
H23B 0.575(3) 0.4718(13) 0.252(3) 0.114(9) Uiso d . 1 . . H
H22C 0.522(3) -0.0119(14) 0.911(3) 0.116(9) Uiso d . 1 . . H
H23A 0.555(3) 0.4363(13) 0.124(3) 0.112(9) Uiso d . 1 . . H
H22B 0.447(3) -0.0596(15) 0.783(3) 0.130(11) Uiso d . 1 . . H
H23C 0.671(2) 0.4962(12) 0.181(2) 0.092(7) Uiso d . 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
F1 0.1069(10) 0.0639(7) 0.1599(13) 0.0262(7) 0.0866(10) -0.0064(8)
O1 0.0650(7) 0.0424(6) 0.0790(8) 0.0106(5) 0.0402(7) 0.0023(6)
O2 0.0616(7) 0.0595(8) 0.0907(9) 0.0040(6) 0.0375(7) 0.0307(7)
N1 0.0440(7) 0.0343(7) 0.0515(7) 0.0028(5) 0.0240(6) 0.0015(6)
C1 0.0405(8) 0.0382(8) 0.0486(9) -0.0014(6) 0.0205(7) 0.0011(7)
C2 0.0441(8) 0.0419(9) 0.0513(9) 0.0017(7) 0.0261(7) 0.0001(7)
C3 0.0404(8) 0.0380(8) 0.0477(9) 0.0008(6) 0.0146(7) -0.0026(7)
C4 0.0518(10) 0.0401(9) 0.0580(10) 0.0037(8) 0.0213(8) 0.0095(8)
C5 0.0616(10) 0.0524(10) 0.0488(9) 0.0055(8) 0.0256(8) 0.0092(8)
C6 0.0602(11) 0.0470(10) 0.0577(10) 0.0059(8) 0.0344(9) 0.0067(8)
C7 0.0431(8) 0.0359(8) 0.0456(8) 0.0010(6) 0.0193(7) 0.0014(6)
C8 0.0419(8) 0.0365(8) 0.0473(8) 0.0017(6) 0.0196(7) -0.0003(7)
C9 0.0442(8) 0.0354(8) 0.0483(8) 0.0030(6) 0.0225(7) 0.0023(7)
C10 0.0478(9) 0.0457(10) 0.0683(11) -0.0037(8) 0.0234(9) -0.0082(8)
C11 0.0736(13) 0.0419(10) 0.0824(13) -0.0031(9) 0.0393(11) -0.0156(9)
C12 0.0724(12) 0.0415(10) 0.0892(13) 0.0145(9) 0.0500(11) 0.0037(9)
C13 0.0465(10) 0.0550(11) 0.0947(14) 0.0075(9) 0.0346(10) 0.0043(10)
C14 0.0457(9) 0.0419(9) 0.0669(11) -0.0016(7) 0.0231(8) -0.0031(8)
C15 0.0437(8) 0.0379(8) 0.0473(8) -0.0003(6) 0.0210(7) 0.0009(7)
C16 0.0439(9) 0.0492(10) 0.0678(11) 0.0064(8) 0.0269(8) 0.0127(8)
C17 0.0451(9) 0.0554(11) 0.0770(12) 0.0007(8) 0.0323(9) 0.0142(9)
C18 0.0518(9) 0.0430(9) 0.0513(9) -0.0018(7) 0.0267(8) 0.0056(7)
C19 0.0456(9) 0.0536(10) 0.0603(10) 0.0060(8) 0.0205(8) 0.0151(8)
C20 0.0396(8) 0.0557(10) 0.0684(11) -0.0023(8) 0.0212(8) 0.0124(9)
C21 0.111(2) 0.0746(15) 0.0873(17) 0.0171(15) 0.0656(17) 0.0314(14)
C22 0.0902(16) 0.0896(18) 0.0526(12) 0.0009(15) 0.0149(12) -0.0037(12)
C23 0.0764(15) 0.0693(15) 0.1024(19) 0.0072(13) 0.0374(15) 0.0427(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C12 . 1.3545(18) ?
O1 C3 . 1.2252(17) ?
O2 C18 . 1.3613(18) ?
O2 C23 . 1.409(2) ?
N1 C7 . 1.3667(18) ?
N1 C1 . 1.4065(18) ?
N1 C9 . 1.4352(18) ?
C1 C2 . 1.353(2) ?
C1 C15 . 1.475(2) ?
C2 C8 . 1.422(2) ?
C2 H2 . 0.953(15) ?
C3 C8 . 1.446(2) ?
C3 C4 . 1.508(2) ?
C4 C5 . 1.529(2) ?
C4 H4A . 0.962(18) ?
C4 H4B . 0.996(18) ?
C5 C22 . 1.523(3) ?
C5 C21 . 1.531(3) ?
C5 C6 . 1.537(2) ?
C6 C7 . 1.485(2) ?
C6 H6A . 0.981(19) ?
C6 H6B . 1.001(18) ?
C7 C8 . 1.3717(19) ?
C9 C14 . 1.373(2) ?
C9 C10 . 1.375(2) ?
C10 C11 . 1.381(2) ?
C10 H10 . 0.972(18) ?
C11 C12 . 1.359(3) ?
C11 H11 . 0.97(2) ?
C12 C13 . 1.365(3) ?
C13 C14 . 1.377(2) ?
C13 H13 . 0.96(2) ?
C14 H14 . 0.956(17) ?
C15 C20 . 1.380(2) ?
C15 C16 . 1.388(2) ?
C16 C17 . 1.368(2) ?
C16 H16 . 0.968(19) ?
C17 C18 . 1.379(2) ?
C17 H17 . 0.976(19) ?
C18 C19 . 1.374(2) ?
C19 C20 . 1.389(2) ?
C19 H19 . 0.967(19) ?
C20 H20 . 0.974(18) ?
C21 H22A . 0.96(2) ?
C21 H22C . 0.96(3) ?
C21 H22B . 1.01(3) ?
C22 H21A . 0.99(2) ?
C22 H21B . 1.01(3) ?
C22 H21C . 0.99(3) ?
C23 H23B . 0.95(3) ?
C23 H23A . 0.97(3) ?
C23 H23C . 0.93(2) ?