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#$Date: 2016-03-26 00:07:36 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180061 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/07/7050703.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_7050703
loop_
_publ_author_name
'Wilhelm, Michaela'
'Koch, Rainer'
'Strasdeit, Henry'
_publ_section_title
;
Coordination chemistry of lipoic acid and related compounds. Part 4.
Experimental and theoretical studies on the 1:2 proton complex of N-(1-
adamantyl)lipoamide
;
_journal_name_full               'New Journal of Chemistry'
_journal_year                    2002
_chemical_formula_sum            'C38 H61 Cl7 N2 O2 S4'
_chemical_formula_weight         954.28
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 102.340(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.9150(10)
_cell_length_b                   19.7570(10)
_cell_length_c                   19.0100(10)
_cell_measurement_temperature    193(2)
_cell_volume                     4738.6(5)
_diffrn_ambient_temperature      193(2)
_exptl_crystal_density_diffrn    1.338
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7050703
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S1A S 0.1560(2) 0.71601(11) 0.36083(15) 0.0955(7) Uani 0.85 1 d P A 1
S1B S 0.1127(14) 0.7023(9) 0.2901(11) 0.122(5) Uiso 0.15 1 d P A 2
S2 S 0.24910(14) 0.68410(7) 0.29508(12) 0.0868(6) Uani 1 1 d . . .
O1 O 0.6095(2) 0.38383(13) 0.26687(19) 0.0487(8) Uani 1 1 d D A .
H12 H 0.5198(16) 0.377(2) 0.231(2) 0.058 Uiso 1 1 d D A .
N1 N 0.7253(2) 0.46406(15) 0.3169(2) 0.0349(8) Uani 1 1 d . A .
H1N H 0.7362 0.5078 0.3231 0.042 Uiso 1 1 calc R A .
C1 C 0.0588(5) 0.6533(4) 0.3328(4) 0.087(2) Uani 1 1 d . . .
H1A H 0.0103 0.6511 0.3666 0.105 Uiso 1 1 calc R A 1
H1B H 0.0166 0.6642 0.2843 0.105 Uiso 1 1 calc R A 1
C2 C 0.1123(5) 0.5891(3) 0.3314(5) 0.093(2) Uani 1 1 d . A .
H2A H 0.0604 0.5543 0.3091 0.111 Uiso 1 1 calc R . .
H2B H 0.1436 0.5746 0.3813 0.111 Uiso 1 1 calc R . .
C3 C 0.2029(5) 0.5954(3) 0.2870(4) 0.0785(19) Uani 1 1 d . A .
H3 H 0.1713 0.5859 0.2352 0.094 Uiso 1 1 calc R . .
C4 C 0.2886(4) 0.5470(2) 0.3119(4) 0.0625(15) Uani 1 1 d . . .
H4A H 0.2581 0.5009 0.3093 0.075 Uiso 1 1 calc R A .
H4B H 0.3204 0.5566 0.3631 0.075 Uiso 1 1 calc R . .
C5 C 0.3768(4) 0.5480(2) 0.2692(3) 0.0555(14) Uani 1 1 d . A .
H5A H 0.3465 0.5361 0.2184 0.067 Uiso 1 1 calc R . .
H5B H 0.4063 0.5943 0.2702 0.067 Uiso 1 1 calc R . .
C6 C 0.4647(3) 0.4992(2) 0.2995(3) 0.0464(11) Uani 1 1 d . . .
H6A H 0.4352 0.4529 0.2995 0.056 Uiso 1 1 calc R A .
H6B H 0.4964 0.5117 0.3499 0.056 Uiso 1 1 calc R . .
C7 C 0.5502(3) 0.4999(2) 0.2552(3) 0.0383(10) Uani 1 1 d . A .
H7A H 0.5170 0.4927 0.2038 0.046 Uiso 1 1 calc R . .
H7B H 0.5852 0.5448 0.2597 0.046 Uiso 1 1 calc R . .
C8 C 0.6316(3) 0.44597(19) 0.2798(2) 0.0372(10) Uani 1 1 d . . .
C9 C 0.8154(3) 0.41911(19) 0.3497(2) 0.0361(10) Uani 1 1 d . . .
C10 C 0.9071(3) 0.4660(2) 0.3823(3) 0.0457(11) Uani 1 1 d . A .
H10A H 0.8861 0.4956 0.4189 0.055 Uiso 1 1 calc R . .
H10B H 0.9250 0.4952 0.3442 0.055 Uiso 1 1 calc R . .
C11 C 0.7865(4) 0.3756(2) 0.4092(3) 0.0470(11) Uani 1 1 d . A .
H11A H 0.7270 0.3450 0.3886 0.056 Uiso 1 1 calc R . .
H11B H 0.7641 0.4048 0.4456 0.056 Uiso 1 1 calc R . .
C12 C 0.8486(4) 0.3743(2) 0.2926(3) 0.0462(11) Uani 1 1 d . A .
H12A H 0.8669 0.4028 0.2542 0.055 Uiso 1 1 calc R . .
H12B H 0.7894 0.3441 0.2706 0.055 Uiso 1 1 calc R . .
C13 C 1.0041(4) 0.4236(3) 0.4172(3) 0.0579(14) Uani 1 1 d . . .
H13 H 1.0642 0.4544 0.4381 0.069 Uiso 1 1 calc R A .
C14 C 0.9752(4) 0.3809(3) 0.4773(3) 0.0660(15) Uani 1 1 d . A .
H14A H 1.0374 0.3541 0.5016 0.079 Uiso 1 1 calc R . .
H14B H 0.9535 0.4107 0.5135 0.079 Uiso 1 1 calc R . .
C15 C 0.8847(4) 0.3338(3) 0.4448(3) 0.0605(14) Uani 1 1 d . . .
H15 H 0.8666 0.3050 0.4837 0.073 Uiso 1 1 calc R A .
C16 C 0.9157(5) 0.2880(3) 0.3875(3) 0.0666(16) Uani 1 1 d . A .
H16A H 0.9766 0.2592 0.4098 0.080 Uiso 1 1 calc R . .
H16B H 0.8556 0.2582 0.3663 0.080 Uiso 1 1 calc R . .
C17 C 0.9455(4) 0.3318(3) 0.3289(3) 0.0578(14) Uani 1 1 d . . .
H17 H 0.9672 0.3020 0.2921 0.069 Uiso 1 1 calc R A .
C18 C 1.0363(4) 0.3782(3) 0.3611(3) 0.0660(16) Uani 1 1 d . A .
H18A H 1.0557 0.4062 0.3227 0.079 Uiso 1 1 calc R . .
H18B H 1.0989 0.3509 0.3837 0.079 Uiso 1 1 calc R . .
S3A S 0.7233(8) 0.0524(4) 0.5308(5) 0.200(3) Uani 0.50 1 d PD B 4
S4A S 0.7184(4) 0.1081(4) 0.4570(3) 0.144(2) Uani 0.50 1 d PD B 4
S3B S 0.5423(5) 0.0778(3) 0.5468(3) 0.1308(18) Uani 0.50 1 d PD C 3
S4B S 0.6000(4) 0.0548(2) 0.4625(3) 0.1127(16) Uani 0.50 1 d PD C 3
O2 O 0.4301(2) 0.36185(13) 0.19875(19) 0.0491(9) Uani 1 1 d D . .
N2 N 0.3022(2) 0.28436(15) 0.1637(2) 0.0362(8) Uani 1 1 d . . .
H2N H 0.2871 0.2409 0.1598 0.043 Uiso 1 1 calc R A .
C19A C 0.6553(14) 0.0960(8) 0.5915(10) 0.107(5) Uiso 0.50 1 d PD B 4
H19A H 0.5801 0.0818 0.5836 0.128 Uiso 0.50 1 calc PR B 4
H19B H 0.6901 0.0876 0.6424 0.128 Uiso 0.50 1 calc PR B 4
C20A C 0.6635(13) 0.1611(7) 0.5739(8) 0.074(3) Uiso 0.50 1 d PD B 4
H20A H 0.7273 0.1811 0.6053 0.089 Uiso 0.50 1 calc PR B 4
H20B H 0.6008 0.1863 0.5819 0.089 Uiso 0.50 1 calc PR B 4
C21A C 0.6729(11) 0.1698(7) 0.4821(8) 0.078(4) Uiso 0.50 1 d PD B 4
H21A H 0.7311 0.2037 0.4847 0.094 Uiso 0.50 1 calc PR B 4
C19B C 0.6045(19) 0.1523(12) 0.5681(13) 0.142(8) Uiso 0.50 1 d PD C 3
H19C H 0.5568 0.1892 0.5458 0.171 Uiso 0.50 1 calc PR C 3
H19D H 0.6180 0.1584 0.6209 0.171 Uiso 0.50 1 calc PR C 3
C20B C 0.713(2) 0.1590(17) 0.5430(18) 0.192(12) Uiso 0.50 1 d PD C 3
H20C H 0.7678 0.1259 0.5660 0.231 Uiso 0.50 1 calc PR C 3
H20D H 0.7424 0.2055 0.5465 0.231 Uiso 0.50 1 calc PR C 3
C21B C 0.648(3) 0.1365(16) 0.4574(17) 0.26(2) Uiso 0.50 1 d PD C 3
H21B H 0.7023 0.1341 0.4272 0.316 Uiso 0.50 1 calc PR C 3
C22 C 0.5789(7) 0.2045(4) 0.4334(4) 0.097(2) Uani 1 1 d D C 3
H22A H 0.5094 0.2028 0.4473 0.117 Uiso 0.50 1 calc PR C 3
H22B H 0.6176 0.2457 0.4539 0.117 Uiso 0.50 1 calc PR C 3
C22D C 0.5789(7) 0.2045(4) 0.4334(4) 0.097(2) Uani 0.00 1 d P B 4
H22C H 0.5136 0.1854 0.4448 0.117 Uiso 0.50 1 calc PR B 4
H22D H 0.5813 0.2530 0.4470 0.117 Uiso 0.50 1 calc PR B 4
C23 C 0.5671(6) 0.2011(3) 0.3521(4) 0.0796(18) Uani 1 1 d . . .
H23A H 0.6360 0.2118 0.3399 0.095 Uiso 1 1 calc R C 3
H23B H 0.5477 0.1543 0.3356 0.095 Uiso 1 1 calc R C 3
C24 C 0.4846(4) 0.2490(2) 0.3128(3) 0.0502(12) Uani 1 1 d . A .
H24A H 0.5042 0.2957 0.3292 0.060 Uiso 1 1 calc R . .
H24B H 0.4157 0.2383 0.3252 0.060 Uiso 1 1 calc R . .
C25 C 0.4720(3) 0.2456(2) 0.2316(3) 0.0430(11) Uani 1 1 d . . .
H25A H 0.5422 0.2507 0.2191 0.052 Uiso 1 1 calc R A .
H25B H 0.4430 0.2008 0.2140 0.052 Uiso 1 1 calc R . .
C26 C 0.3995(3) 0.3000(2) 0.1956(3) 0.0391(10) Uani 1 1 d . A .
C27 C 0.2142(3) 0.33157(18) 0.1332(2) 0.0337(9) Uani 1 1 d . A .
C28 C 0.1168(3) 0.2874(2) 0.1034(3) 0.0426(11) Uani 1 1 d . . .
H28A H 0.1319 0.2572 0.0653 0.051 Uiso 1 1 calc R A .
H28B H 0.1002 0.2589 0.1424 0.051 Uiso 1 1 calc R . .
C29 C 0.2397(4) 0.3750(2) 0.0717(3) 0.0450(11) Uani 1 1 d . . .
H29A H 0.3029 0.4033 0.0901 0.054 Uiso 1 1 calc R A .
H29B H 0.2550 0.3454 0.0332 0.054 Uiso 1 1 calc R . .
C30 C 0.1905(3) 0.3774(2) 0.1931(3) 0.0408(10) Uani 1 1 d . . .
H30A H 0.2530 0.4059 0.2127 0.049 Uiso 1 1 calc R A .
H30B H 0.1748 0.3494 0.2327 0.049 Uiso 1 1 calc R . .
C31 C 0.0219(3) 0.3328(2) 0.0724(3) 0.0479(12) Uani 1 1 d . A .
H31 H -0.0415 0.3041 0.0530 0.057 Uiso 1 1 calc R . .
C32 C 0.0475(4) 0.3761(3) 0.0122(3) 0.0576(13) Uani 1 1 d . . .
H32A H -0.0140 0.4052 -0.0083 0.069 Uiso 1 1 calc R A .
H32B H 0.0620 0.3466 -0.0267 0.069 Uiso 1 1 calc R . .
C33 C 0.1444(4) 0.4202(2) 0.0416(3) 0.0521(12) Uani 1 1 d . A .
H33 H 0.1605 0.4488 0.0019 0.063 Uiso 1 1 calc R . .
C34 C 0.1213(4) 0.4659(2) 0.1015(3) 0.0584(14) Uani 1 1 d . . .
H34A H 0.1841 0.4943 0.1209 0.070 Uiso 1 1 calc R A .
H34B H 0.0612 0.4963 0.0817 0.070 Uiso 1 1 calc R . .
C35 C 0.0944(4) 0.4225(2) 0.1615(3) 0.0507(12) Uani 1 1 d . A .
H35 H 0.0786 0.4526 0.2002 0.061 Uiso 1 1 calc R . .
C36 C -0.0017(4) 0.3790(3) 0.1318(3) 0.0559(13) Uani 1 1 d . . .
H36A H -0.0632 0.4083 0.1120 0.067 Uiso 1 1 calc R A .
H36B H -0.0195 0.3512 0.1709 0.067 Uiso 1 1 calc R . .
Cl1 Cl 0.75221(9) 0.62466(5) 0.34432(7) 0.0473(3) Uani 1 1 d . . .
C1S C 0.2019(4) 0.3849(3) -0.1771(3) 0.0621(14) Uani 1 1 d . . .
H1S H 0.2151 0.3879 -0.2270 0.093 Uiso 1 1 calc R D 8
Cl2A Cl 0.0973(7) 0.4419(4) -0.1693(4) 0.0897(19) Uani 0.75 1 d P E 8
Cl3A Cl 0.1670(9) 0.3038(5) -0.1616(7) 0.096(2) Uani 0.75 1 d P E 8
Cl4A Cl 0.3168(5) 0.4076(3) -0.1159(4) 0.128(2) Uani 0.75 1 d P E 8
Cl2B Cl 0.127(2) 0.4518(11) -0.1680(12) 0.110(9) Uani 0.25 1 d P E 9
Cl3B Cl 0.145(3) 0.3037(12) -0.1576(19) 0.090(7) Uani 0.25 1 d P E 9
Cl4B Cl 0.3293(11) 0.3977(4) -0.1224(9) 0.065(3) Uani 0.25 1 d P E 9
C2S C 0.3722(5) 0.3695(3) 0.5160(4) 0.0744(17) Uani 1 1 d . . .
H2S H 0.3309 0.3767 0.5543 0.112 Uiso 1 1 calc R F 5
Cl5A Cl 0.3167(7) 0.3017(7) 0.4608(8) 0.084(3) Uani 0.50 1 d P G 5
Cl6A Cl 0.5045(13) 0.3528(7) 0.5564(7) 0.085(5) Uani 0.50 1 d P G 5
Cl7A Cl 0.368(2) 0.4378(14) 0.4683(16) 0.223(13) Uani 0.50 1 d P G 5
Cl5B Cl 0.319(2) 0.2889(15) 0.4768(19) 0.088(7) Uani 0.25 1 d P G 6
Cl6B Cl 0.5131(19) 0.3704(15) 0.5224(13) 0.192(15) Uani 0.25 1 d P G 6
Cl7B Cl 0.3350(18) 0.4391(11) 0.470(2) 0.123(8) Uani 0.25 1 d P G 6
Cl5C Cl 0.3277(8) 0.3450(8) 0.4280(7) 0.123(4) Uani 0.25 1 d P G 7
Cl6C Cl 0.488(3) 0.3411(19) 0.562(2) 0.094(8) Uani 0.25 1 d P G 7
Cl7C Cl 0.361(3) 0.4670(17) 0.4996(11) 0.126(6) Uani 0.25 1 d P G 7
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
S1A C1 1.763(8) . ?
S1A S2 2.012(3) . ?
S1B C1 1.52(2) . ?
S1B S2 1.781(18) . ?
S2 C3 1.847(6) . ?
O1 H12 1.221(8) . ?
O1 C8 1.273(5) . ?
O1 O2 2.439(4) . ?
N1 C8 1.313(5) . ?
N1 C9 1.490(5) . ?
N1 Cl1 3.222(3) . ?
C1 C2 1.448(9) . ?
C2 C3 1.587(8) . ?
C3 C4 1.463(8) . ?
C4 C5 1.533(7) . ?
C5 C6 1.507(7) . ?
C6 C7 1.526(6) . ?
C7 C8 1.501(5) . ?
C9 C10 1.528(6) . ?
C9 C11 1.530(6) . ?
C9 C12 1.531(6) . ?
C10 C13 1.535(6) . ?
C11 C15 1.543(7) . ?
C12 C17 1.542(6) . ?
C13 C18 1.520(8) . ?
C13 C14 1.529(8) . ?
C14 C15 1.518(8) . ?
C15 C16 1.533(8) . ?
C16 C17 1.522(8) . ?
C17 C18 1.511(8) . ?
S3A S4A 1.774(11) . ?
S3A C19A 1.810(18) . ?
S4A C21A 1.476(15) . ?
S3B C19B 1.68(2) . ?
S3B S4B 1.960(7) . ?
S4B C21B 1.74(3) . ?
O2 H12 1.224(8) . ?
O2 C26 1.282(5) . ?
N2 C26 1.311(5) . ?
N2 C27 1.488(5) . ?
C19A C20A 1.34(2) . ?
C20A C21A 1.78(2) . ?
C19B C20B 1.58(3) . ?
C20B C21B 1.73(3) . ?
C21B C22 1.62(3) . ?
C22 C23 1.522(10) . ?
C23 C24 1.499(7) . ?
C24 C25 1.519(7) . ?
C25 C26 1.492(6) . ?
C27 C30 1.535(6) . ?
C27 C28 1.537(5) . ?
C27 C29 1.541(6) . ?
C28 C31 1.532(6) . ?
C29 C33 1.529(7) . ?
C30 C35 1.541(6) . ?
C31 C32 1.521(7) . ?
C31 C36 1.531(7) . ?
C32 C33 1.529(7) . ?
C33 C34 1.531(7) . ?
C34 C35 1.526(7) . ?
C35 C36 1.516(7) . ?
Cl1 H1N 2.3447 . ?
Cl1 H2N 2.3497 2_655 ?
Cl1 H1S 2.3703 3_665 ?
Cl1 H2S 2.3984 3_666 ?
Cl1 N2 3.229(3) 2_655 ?
Cl1 C1S 3.361(6) 3_665 ?
Cl1 C2S 3.386(7) 3_666 ?
C1S Cl2B 1.666(19) . ?
C1S Cl3A 1.707(10) . ?
C1S Cl4A 1.738(9) . ?
C1S Cl4B 1.767(17) . ?
C1S Cl2A 1.789(8) . ?
C1S Cl3B 1.84(3) . ?
C2S Cl7A 1.620(19) . ?
C2S Cl7B 1.65(2) . ?
C2S Cl6C 1.66(4) . ?
C2S Cl5C 1.718(13) . ?
C2S Cl6A 1.748(17) . ?
C2S Cl5A 1.756(15) . ?
C2S Cl6B 1.80(3) . ?
C2S Cl5B 1.83(3) . ?
C2S Cl7C 1.95(3) . ?
