#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/05/4020572.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_4020572
loop_
_publ_author_name
'Michael C. Hillier'
'Jean-François Marcoux'
'Dalian Zhao'
'Edward J. J. Grabowski'
'Arlene E. McKeown'
'Richard D. Tillyer'
_publ_section_title
;
 Stereoselective Formation of Carbon-Carbon Bonds
 via SN2-Displacement: Synthesis of Substituted
 Cycloalkyl[b]indoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8385
_journal_page_last               8394
_journal_paper_doi               10.1021/jo051146p
_journal_volume                  70
_journal_year                    2005
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H14 Br Cl F N O'
_chemical_formula_sum            'C18 H14 Br Cl F N O'
_chemical_formula_weight         394.66
_chemical_melting_point          124.0(10)
_chemical_name_common            'Compound 14a'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.2721(13)
_cell_length_b                   12.916(3)
_cell_length_c                   23.515(6)
_cell_measurement_temperature    223(2)
_cell_volume                     1601.3(7)
_diffrn_ambient_temperature      223(2)
_exptl_crystal_density_diffrn    1.637
_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 '123-125' was changed to '124.0(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               4020572
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'
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
Br1 Br 1.01373(7) 0.46101(2) 0.750542(13) 0.04281(12) Uani 1 1 d . . .
C1 C 0.8212(6) 0.3396(2) 0.73585(13) 0.0323(8) Uani 1 1 d . . .
C2 C 0.6302(6) 0.3161(3) 0.77340(13) 0.0358(8) Uani 1 1 d . . .
H2 H 0.5994 0.3596 0.8047 0.043 Uiso 1 1 calc R . .
C3 C 0.4831(6) 0.2289(3) 0.76530(13) 0.0413(8) Uani 1 1 d . . .
C4 C 0.5192(7) 0.1611(2) 0.72125(13) 0.0374(7) Uani 1 1 d . . .
H4 H 0.4177 0.1017 0.7170 0.045 Uiso 1 1 calc R . .
C5 C 0.7145(6) 0.1841(2) 0.68271(12) 0.0283(7) Uani 1 1 d . . .
C6 C 0.8023(6) 0.1341(2) 0.63241(13) 0.0297(7) Uani 1 1 d . . .
C7 C 0.7670(7) 0.0361(2) 0.59833(14) 0.0368(8) Uani 1 1 d . . .
H7A H 0.5965 0.0324 0.5818 0.044 Uiso 1 1 calc R . .
H7B H 0.7967 -0.0256 0.6217 0.044 Uiso 1 1 calc R . .
C8 C 0.9708(9) 0.0474(3) 0.55186(15) 0.0595(12) Uani 1 1 d . . .
H8A H 1.0925 -0.0097 0.5548 0.071 Uiso 1 1 calc R . .
H8B H 0.8908 0.0439 0.5143 0.071 Uiso 1 1 calc R . .
C9 C 1.1100(7) 0.1508(2) 0.55832(13) 0.0358(8) Uani 1 1 d . . .
H9 H 1.2917 0.1368 0.5657 0.043 Uiso 1 1 calc R . .
C10 C 0.9924(6) 0.1922(2) 0.61135(11) 0.0295(7) Uani 1 1 d . . .
C11 C 0.8656(6) 0.2749(2) 0.68898(12) 0.0276(7) Uani 1 1 d . . .
C12 C 1.2455(6) 0.3511(2) 0.63399(13) 0.0312(7) Uani 1 1 d . . .
H12A H 1.3635 0.3194 0.6069 0.037 Uiso 1 1 calc R . .
H12B H 1.3371 0.3612 0.6698 0.037 Uiso 1 1 calc R . .
C13 C 1.1675(6) 0.4563(2) 0.61123(13) 0.0303(7) Uani 1 1 d . . .
C14 C 0.9559(7) 0.4717(2) 0.57819(13) 0.0362(8) Uani 1 1 d . . .
H14 H 0.8534 0.4149 0.5683 0.043 Uiso 1 1 calc R . .
C15 C 0.8915(7) 0.5701(2) 0.55925(15) 0.0410(9) Uani 1 1 d . . .
H15 H 0.7461 0.5800 0.5368 0.049 Uiso 1 1 calc R . .
C16 C 1.0416(8) 0.6524(2) 0.57362(13) 0.0394(9) Uani 1 1 d . . .
C17 C 1.2576(8) 0.6392(3) 0.60511(14) 0.0451(9) Uani 1 1 d . . .
H17 H 1.3623 0.6960 0.6138 0.054 Uiso 1 1 calc R . .
C18 C 1.3192(7) 0.5407(2) 0.62396(14) 0.0386(8) Uani 1 1 d . . .
H18 H 1.4667 0.5310 0.6458 0.046 Uiso 1 1 calc R . .
Cl1 Cl 0.9504(2) 0.77691(6) 0.55371(4) 0.0625(3) Uani 1 1 d . . .
F1 F 0.2950(4) 0.20984(17) 0.80367(9) 0.0554(6) Uani 1 1 d . . .
N1 N 1.0355(5) 0.27874(16) 0.64407(9) 0.0282(6) Uani 1 1 d . . .
O1 O 1.0898(4) 0.21768(17) 0.51033(9) 0.0361(5) Uani 1 1 d . . .
H1 H 0.9410 0.2378 0.5071 0.054 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
Br1 C1 1.900(3) . ?
C1 C2 1.373(4) . ?
C1 C11 1.403(4) . ?
C2 C3 1.381(5) . ?
C2 H2 0.9400 . ?
C3 F1 1.363(4) . ?
C3 C4 1.370(5) . ?
C4 C5 1.403(4) . ?
C4 H4 0.9400 . ?
C5 C6 1.425(4) . ?
C5 C11 1.426(4) . ?
C6 C10 1.347(4) . ?
C6 C7 1.510(4) . ?
C7 C8 1.539(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 C9 1.532(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 O1 1.425(3) . ?
C9 C10 1.491(4) . ?
C9 H9 0.9900 . ?
C10 N1 1.376(3) . ?
C11 N1 1.386(4) . ?
C12 N1 1.468(4) . ?
C12 C13 1.517(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 C14 1.374(4) . ?
C13 C18 1.384(4) . ?
C14 C15 1.389(4) . ?
C14 H14 0.9400 . ?
C15 C16 1.368(5) . ?
C15 H15 0.9400 . ?
C16 C17 1.369(5) . ?
C16 Cl1 1.742(3) . ?
C17 C18 1.386(5) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
O1 H1 0.8300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9892880
