#------------------------------------------------------------------------------
#$Date: 2009-11-14 13:09:05 +0000 (Sat, 14 Nov 2009) $
#$Revision: 846 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006644.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_2006644
_journal_volume                  C53
_journal_year  1997
_journal_page_first  1713
_journal_page_last  1714
_publ_section_title
;
Unusual Substitution of -SCH~3~ by -OH in 9,10-Dihydrophenanthrene
;
loop_
_publ_author_name
  'Sarkhel, Sanjay'
  'Goel, Atul'
  'Ram, Vishnu J.'
  'Chaudhuri, Siddhartha'
  'Maulik, Prakas R.'
_chemical_name_common  '9,10-dihydrophenanthrene'
_chemical_formula_sum  'C23 H19 Cl O4'
_chemical_formula_weight  394.83
_chemical_melting_point  '160-162 \%C'
_symmetry_cell_setting  Triclinic
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  8.9047(7)
_cell_length_b  9.6102(13)
_cell_length_c  12.9962(15)
_cell_angle_alpha  110.332(12)
_cell_angle_beta  104.167(8)
_cell_angle_gamma  97.458(8)
_cell_volume  982.5(2)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.335
_diffrn_ambient_temperature  293(2)
_refine_ls_R_factor_obs  .0646
_refine_ls_wR_factor_obs  .2228
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  C4  .3016(3)  .6605(3)  -.0295(2)  .0387(6) Uani d . 1 . C
  C4"A  .2582(3)  .7686(2)  -.0827(2)  .0414(6) Uani d . 1 . C
  O4"A  .3495(2)  .8847(2)  -.0669(2)  .0571(6) Uani d . 1 . O
  O4"B  .1046(2)  .7347(2)  -.1412(2)  .0529(5) Uani d . 1 . O
  C4"B  .0520(4)  .8320(4)  -.1980(4)  .0785(11) Uani d . 1 . C
  H4"1  -.0593(9)  .7929(19)  -.241(2)  .118 Uiso calc R 1 . H
  H4"2  .112(2)  .835(3)  -.2500(19)  .118 Uiso calc R 1 . H
  H4"3  .069(3)  .9333(9)  -.1414(4)  .118 Uiso calc R 1 . H
  C4A  .2216(3)  .5052(3)  -.0756(2)  .0382(6) Uani d . 1 . C
  C3  .4132(3)  .7246(3)  .0814(2)  .0423(6) Uani d . 1 . C
  O3"  .5063(2)  .8683(2)  .1290(2)  .0550(6) Uani d . 1 . O
  H3"  .499(4)  .9040(17)  .0796(8)  .083 Uiso calc R 1 . H
  C2  .4286(3)  .6403(3)  .1495(2)  .0475(7) Uani d . 1 . C
  H2  .5027(3)  .6831(3)  .2230(2)  .057 Uiso calc R 1 . H
  C1  .3359(3)  .4939(3)  .1103(2)  .0438(6) Uani d . 1 . C
  C1A  .2339(3)  .4227(3)  -.0047(2)  .0408(6) Uani d . 1 . C
  C10  .1329(3)  .2612(3)  -.0539(2)  .0463(7) Uani d . 1 . C
  H10A  .1125(3)  .2360(3)  .0083(2)  .056 Uiso calc R 1 . H
  H10B  .1903(3)  .1905(3)  -.0911(2)  .056 Uiso calc R 1 . H
  C9  -.0245(3)  .2446(3)  -.1409(2)  .0487(7) Uani d . 1 . C
  H9A  -.0855(3)  .1395(3)  -.1745(2)  .058 Uiso calc R 1 . H
  H9B  -.0864(3)  .3088(3)  -.1027(2)  .058 Uiso calc R 1 . H
  C9A  .0084(3)  .2908(3)  -.2341(2)  .0415(6) Uani d . 1 . C
  C8  -.0762(3)  .2077(3)  -.3503(2)  .0514(7) Uani d . 1 . C
  H8  -.1582(3)  .1227(3)  -.3718(2)  .062 Uiso calc R 1 . H
  C7  -.0395(4)  .2501(3)  -.4337(3)  .0585(8) Uani d . 1 . C
  O7"  -.1153(3)  .1758(3)  -.5496(2)  .0876(9) Uani d . 1 . O
  C7"  -.2319(5)  .0382(4)  -.5895(3)  .0848(12) Uani d . 1 . C
  H7"1  -.276(3)  -.0003(19)  -.6720(4)  .127 Uiso calc R 1 . H
  H7"2  -.3153(18)  .0571(8)  -.555(2)  .127 Uiso calc R 1 . H
  H7"3  -.1838(9)  -.0357(12)  -.568(2)  .127 Uiso calc R 1 . H
  C6  .0840(4)  .3763(3)  -.4010(3)  .0610(8) Uani d . 1 . C
  H6  .1090(4)  .4055(3)  -.4571(3)  .073 Uiso calc R 1 . H
  C5  .1694(3)  .4583(3)  -.2869(2)  .0508(7) Uani d . 1 . C
  H5  .2542(3)  .5403(3)  -.2667(2)  .061 Uiso calc R 1 . H
  C5A  .1309(3)  .4203(3)  -.2003(2)  .0401(6) Uani d . 1 . C
  C1'  .3474(3)  .4168(3)  .1932(2)  .0435(6) Uani d . 1 . C
  C2'  .3867(3)  .2772(3)  .1703(3)  .0524(7) Uani d . 1 . C
  H2'  .4045(3)  .2277(3)  .1005(3)  .063 Uiso calc R 1 . H
  C3'  .4001(3)  .2093(3)  .2493(3)  .0570(8) Uani d . 1 . C
  H3'  .4267(3)  .1153(3)  .2329(3)  .068 Uiso calc R 1 . H
  C4'  .3734(3)  .2832(3)  .3526(3)  .0550(7) Uani d . 1 . C
  C5'  .3361(3)  .4233(3)  .3782(3)  .0557(7) Uani d . 1 . C
  H5'  .3202(3)  .4732(3)  .4486(3)  .067 Uiso calc R 1 . H
  C6'  .3223(3)  .4900(3)  .2978(2)  .0522(7) Uani d . 1 . C
  H6'  .2962(3)  .5842(3)  .3145(2)  .063 Uiso calc R 1 . H
  Cl  .38637(13)  .19813(11)  .45143(8)  .0820(4) Uani d . 1 . Cl
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
  C4  .0334(11)  .0399(12)  .0386(14)  .0016(9)  .0119(10)  .0125(10)
  C4"A  .0381(12)  .0352(12)  .0412(14)  -.0021(9)  .0117(10)  .0082(10)
  O4"A  .0474(10)  .0455(10)  .0694(14)  -.0069(8)  .0074(8)  .0256(9)
  O4"B  .0406(10)  .0446(10)  .0674(13)  -.0018(7)  .0038(8)  .0281(9)
  C4"B  .064(2)  .064(2)  .096(3)  .002(2)  -.008(2)  .045(2)
  C4A  .0337(11)  .0380(12)  .0411(14)  .0051(9)  .0136(9)  .0136(10)
  C3  .0353(12)  .0367(12)  .047(2)  .0009(9)  .0124(10)  .0107(10)
  O3"  .0515(11)  .0443(10)  .0495(12)  -.0100(8)  .0017(9)  .0126(8)
  C2  .0395(13)  .0476(14)  .043(2)  .0025(11)  .0033(10)  .0127(11)
  C1  .0383(12)  .0457(13)  .045(2)  .0097(10)  .0111(10)  .0169(11)
  C1A  .0371(12)  .0364(12)  .0441(15)  .0058(9)  .0129(10)  .0111(10)
  C10  .0480(14)  .0394(13)  .048(2)  .0041(11)  .0119(11)  .0179(11)
  C9  .0415(13)  .0465(14)  .051(2)  -.0012(11)  .0130(11)  .0164(12)
  C9A  .0390(12)  .0346(12)  .048(2)  .0045(10)  .0129(10)  .0142(10)
  C8  .0467(14)  .0466(14)  .046(2)  -.0002(11)  .0097(11)  .0084(12)
  C7  .061(2)  .059(2)  .040(2)  -.0002(14)  .0086(13)  .0114(13)
  O7"  .103(2)  .086(2)  .0385(14)  -.0242(14)  .0041(12)  .0115(11)
  C7"  .085(2)  .080(2)  .050(2)  -.013(2)  -.004(2)  .008(2)
  C6  .068(2)  .066(2)  .041(2)  -.0009(14)  .0200(13)  .0158(13)
  C5  .0504(15)  .0490(14)  .047(2)  -.0016(11)  .0183(12)  .0144(12)
  C5A  .0392(12)  .0368(12)  .0396(15)  .0044(9)  .0118(10)  .0115(10)
  C1'  .0363(12)  .0431(13)  .0436(15)  .0045(10)  .0073(10)  .0137(10)
  C2'  .0513(14)  .054(2)  .056(2)  .0198(12)  .0190(12)  .0215(13)
  C3'  .059(2)  .0464(14)  .065(2)  .0175(12)  .0145(13)  .0237(13)
  C4'  .0485(15)  .060(2)  .055(2)  .0076(12)  .0087(12)  .0276(14)
  C5'  .062(2)  .055(2)  .046(2)  .0083(13)  .0157(13)  .0185(13)
  C6'  .055(2)  .0460(14)  .052(2)  .0149(12)  .0121(12)  .0166(12)
  Cl  .1033(8)  .0783(6)  .0721(7)  .0128(5)  .0204(5)  .0464(5)
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
  C4 C3 . 1.402(3) ?
  C4 C4A . 1.409(3) ?
  C4 C4"A . 1.477(3) ?
  C4"A O4"A . 1.213(3) ?
  C4"A O4"B . 1.326(3) ?
  O4"B C4"B . 1.437(4) ?
  C4"B H4"1 .  .96 ?
  C4"B H4"2 .  .96 ?
  C4"B H4"3 .  .96 ?
  C4A C1A . 1.405(4) ?
  C4A C5A . 1.488(3) ?
  C3 O3" . 1.354(3) ?
  C3 C2 . 1.389(4) ?
  O3" H3" .  .82 ?
  C2 C1 . 1.384(3) ?
  C2 H2 .  .93 ?
  C1 C1A . 1.410(4) ?
  C1 C1' . 1.497(4) ?
  C1A C10 . 1.514(3) ?
  C10 C9 . 1.519(4) ?
  C10 H10A .  .97 ?
  C10 H10B .  .97 ?
  C9 C9A . 1.505(4) ?
  C9 H9A .  .97 ?
  C9 H9B .  .97 ?
  C9A C8 . 1.390(4) ?
  C9A C5A . 1.402(3) ?
  C8 C7 . 1.376(5) ?
  C8 H8 .  .93 ?
  C7 O7" . 1.365(4) ?
  C7 C6 . 1.388(4) ?
  O7" C7" . 1.414(4) ?
  C7" H7"1 .  .96 ?
  C7" H7"2 .  .96 ?
  C7" H7"3 .  .96 ?
  C6 C5 . 1.371(4) ?
  C6 H6 .  .93 ?
  C5 C5A . 1.400(4) ?
  C5 H5 .  .93 ?
  C1' C2' . 1.381(4) ?
  C1' C6' . 1.385(4) ?
  C2' C3' . 1.385(4) ?
  C2' H2' .  .93 ?
  C3' C4' . 1.378(4) ?
  C3' H3' .  .93 ?
  C4' C5' . 1.376(4) ?
  C4' Cl . 1.736(3) ?
  C5' C6' . 1.392(4) ?
  C5' H5' .  .93 ?
  C6' H6' .  .93 ?