#------------------------------------------------------------------------------
#$Date: 2016-03-21 06:11:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178497 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/08/4060819.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_4060819
_journal_name_full               Organometallics
_journal_paper_doi               10.1021/om010856s
_journal_year                    2002
_chemical_formula_sum            'C31 H50 Li N2 O3 P'
_chemical_formula_weight         536.64
_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                 110.635(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.3421(7)
_cell_length_b                   20.8431(7)
_cell_length_c                   16.3715(5)
_cell_measurement_temperature    160(2)
_cell_volume                     6176.7(4)
_diffrn_ambient_temperature      160(2)
_exptl_crystal_density_diffrn    1.154
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4060819
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
Li1 Li 0.2703(2) 0.25273(17) 0.4612(3) 0.0452(9) Uani 1 1 d . . .
P1 P 0.21491(3) 0.24232(3) 0.29768(4) 0.04125(17) Uani 1 1 d . . .
N1 N 0.34158(10) 0.33290(8) 0.46541(11) 0.0382(4) Uani 1 1 d . . .
N2 N 0.19252(10) 0.43967(8) 0.28467(13) 0.0485(5) Uani 1 1 d . . .
O1 O 0.19392(9) 0.27165(8) 0.51022(11) 0.0609(5) Uani 1 1 d . . .
O2 O 0.32686(9) 0.17901(7) 0.52205(10) 0.0507(4) Uani 1 1 d . . .
C1 C 0.17537(13) 0.16371(11) 0.2485(2) 0.0649(8) Uani 1 1 d . . .
H1A H 0.1748 0.1614 0.1885 0.097 Uiso 1 1 calc R . .
H1B H 0.1248 0.1597 0.2483 0.097 Uiso 1 1 calc R . .
H1C H 0.2057 0.1288 0.2830 0.097 Uiso 1 1 calc R . .
C2 C 0.30756(11) 0.23740(9) 0.29544(12) 0.0332(5) Uani 1 1 d . . .
C3 C 0.33356(13) 0.18511(10) 0.25788(14) 0.0397(5) Uani 1 1 d . . .
H3 H 0.3002 0.1514 0.2310 0.048 Uiso 1 1 calc R . .
C4 C 0.40484(13) 0.18138(10) 0.25895(14) 0.0434(6) Uani 1 1 d . . .
H4 H 0.4196 0.1452 0.2339 0.052 Uiso 1 1 calc R . .
C5 C 0.45533(13) 0.22958(10) 0.29604(15) 0.0442(6) Uani 1 1 d . . .
H5 H 0.5047 0.2269 0.2973 0.053 Uiso 1 1 calc R . .
C6 C 0.43145(12) 0.28238(10) 0.33156(14) 0.0402(5) Uani 1 1 d . . .
H6 H 0.4654 0.3162 0.3562 0.048 Uiso 1 1 calc R . .
C7 C 0.36005(11) 0.28741(9) 0.33221(13) 0.0330(5) Uani 1 1 d . . .
C8 C 0.33504(11) 0.34565(9) 0.37228(13) 0.0339(5) Uani 1 1 d . . .
H8 H 0.2807 0.3488 0.3395 0.041 Uiso 1 1 calc R . .
C9 C 0.31066(14) 0.38703(11) 0.50007(16) 0.0541(7) Uani 1 1 d . . .
H9A H 0.3054 0.3743 0.5552 0.081 Uiso 1 1 calc R . .
H9B H 0.2621 0.3986 0.4578 0.081 Uiso 1 1 calc R . .
H9C H 0.3439 0.4240 0.5101 0.081 Uiso 1 1 calc R . .
C10 C 0.41572(13) 0.31637(11) 0.52769(15) 0.0487(6) Uani 1 1 d . . .
H10A H 0.4458 0.3553 0.5439 0.073 Uiso 1 1 calc R . .
H10B H 0.4394 0.2858 0.5004 0.073 Uiso 1 1 calc R . .
H10C H 0.4110 0.2970 0.5800 0.073 Uiso 1 1 calc R . .
C11 C 0.36641(12) 0.40918(9) 0.35374(14) 0.0376(5) Uani 1 1 d . . .
C12 C 0.43854(13) 0.42997(10) 0.39851(15) 0.0460(6) Uani 1 1 d . . .
H12 H 0.4696 0.4047 0.4454 0.055 Uiso 1 1 calc R . .
C13 C 0.46638(15) 0.48650(11) 0.37674(19) 0.0574(7) Uani 1 1 d . . .
H13 H 0.5155 0.4996 0.4088 0.069 Uiso 1 1 calc R . .
C14 C 0.42218(17) 0.52324(11) 0.3084(2) 0.0643(8) Uani 1 1 d . . .
H14 H 0.4410 0.5614 0.2924 0.077 Uiso 1 1 calc R . .
C15 C 0.35046(16) 0.50444(11) 0.26321(17) 0.0561(7) Uani 1 1 d . . .
H15 H 0.3203 0.5303 0.2164 0.067 Uiso 1 1 calc R . .
C16 C 0.32093(13) 0.44825(10) 0.28461(14) 0.0418(5) Uani 1 1 d . . .
C17 C 0.24134(13) 0.43125(11) 0.23372(14) 0.0466(6) Uani 1 1 d . . .
H17A H 0.2232 0.4585 0.1809 0.056 Uiso 1 1 calc R . .
H17B H 0.2388 0.3860 0.2144 0.056 Uiso 1 1 calc R . .
C18 C 0.18796(16) 0.50746(12) 0.3072(2) 0.0699(8) Uani 1 1 d . . .
H18A H 0.1670 0.5327 0.2536 0.105 Uiso 1 1 calc R . .
H18B H 0.2375 0.5234 0.3407 0.105 Uiso 1 1 calc R . .
H18C H 0.1563 0.5114 0.3423 0.105 Uiso 1 1 calc R . .
C19 C 0.11894(14) 0.41379(12) 0.23704(18) 0.0647(8) Uani 1 1 d . . .
H19A H 0.0875 0.4192 0.2721 0.097 Uiso 1 1 calc R . .
H19B H 0.1229 0.3681 0.2255 0.097 Uiso 1 1 calc R . .
H19C H 0.0972 0.4367 0.1816 0.097 Uiso 1 1 calc R . .
C20 C 0.17268(15) 0.22162(15) 0.55704(19) 0.0701(8) Uani 1 1 d . . .
H20A H 0.1990 0.2267 0.6206 0.084 Uiso 1 1 calc R . .
H20B H 0.1851 0.1791 0.5391 0.084 Uiso 1 1 calc R . .
C21 C 0.09116(17) 0.22713(19) 0.5357(3) 0.1032(12) Uani 1 1 d . . .
H21A H 0.0668 0.1848 0.5207 0.124 Uiso 1 1 calc R . .
H21B H 0.0797 0.2456 0.5852 0.124 Uiso 1 1 calc R . .
C22 C 0.0683(2) 0.2691(3) 0.4622(4) 0.191(3) Uani 1 1 d . . .
H22A H 0.0479 0.2435 0.4080 0.230 Uiso 1 1 calc R . .
H22B H 0.0288 0.2978 0.4661 0.230 Uiso 1 1 calc R . .
C23 C 0.12777(19) 0.30584(18) 0.4591(2) 0.0969(12) Uani 1 1 d . . .
H23A H 0.1269 0.3490 0.4839 0.116 Uiso 1 1 calc R . .
H23B H 0.1255 0.3107 0.3981 0.116 Uiso 1 1 calc R . .
C24 C 0.35168(14) 0.16483(12) 0.61433(15) 0.0545(7) Uani 1 1 d . . .
H24A H 0.3146 0.1387 0.6283 0.065 Uiso 1 1 calc R . .
H24B H 0.3603 0.2049 0.6489 0.065 Uiso 1 1 calc R . .
C25 C 0.42175(15) 0.12849(14) 0.63334(18) 0.0675(8) Uani 1 1 d . . .
H25A H 0.4307 0.0995 0.6839 0.081 Uiso 1 1 calc R . .
H25B H 0.4644 0.1578 0.6449 0.081 Uiso 1 1 calc R . .
C26 C 0.40786(17) 0.09103(13) 0.5501(2) 0.0789(9) Uani 1 1 d . . .
H26A H 0.4548 0.0809 0.5415 0.095 Uiso 1 1 calc R . .
H26B H 0.3814 0.0505 0.5509 0.095 Uiso 1 1 calc R . .
C27 C 0.36119(17) 0.13497(13) 0.48010(17) 0.0686(8) Uani 1 1 d . . .
H27A H 0.3921 0.1585 0.4530 0.082 Uiso 1 1 calc R . .
H27B H 0.3232 0.1103 0.4341 0.082 Uiso 1 1 calc R . .
Li2 Li 0.2255(2) 0.75268(19) 0.4989(3) 0.0513(10) Uani 1 1 d . . .
P2 P 0.15807(3) 0.75792(3) 0.60551(4) 0.04660(18) Uani 1 1 d . . .
N3 N 0.29134(10) 0.66847(8) 0.55226(11) 0.0425(5) Uani 1 1 d . . .
N4 N 0.14306(12) 0.55594(10) 0.60033(16) 0.0673(7) Uani 1 1 d . . .
O3 O 0.29085(9) 0.82406(7) 0.49502(10) 0.0518(4) Uani 1 1 d . . .
O4 O 0.15450(11) 0.74097(11) 0.38079(12) 0.0817(6) Uani 1 1 d . . .
C28 C 0.11619(15) 0.83683(13) 0.6164(2) 0.0705(8) Uani 1 1 d . . .
H28A H 0.1090 0.8387 0.6727 0.106 Uiso 1 1 calc R . .
H28B H 0.0684 0.8416 0.5690 0.106 Uiso 1 1 calc R . .
H28C H 0.1492 0.8716 0.6131 0.106 Uiso 1 1 calc R . .
C29 C 0.24893(12) 0.76455(9) 0.68861(14) 0.0371(5) Uani 1 1 d . . .
C30 C 0.27184(13) 0.81662(10) 0.74779(14) 0.0423(5) Uani 1 1 d . . .
H30 H 0.2368 0.8491 0.7458 0.051 Uiso 1 1 calc R . .
C31 C 0.34195(13) 0.82263(10) 0.80777(15) 0.0447(6) Uani 1 1 d . . .
H31 H 0.3546 0.8591 0.8450 0.054 Uiso 1 1 calc R . .
C32 C 0.39447(13) 0.77576(11) 0.81432(14) 0.0441(6) Uani 1 1 d . . .
H32 H 0.4434 0.7800 0.8551 0.053 Uiso 1 1 calc R . .
C33 C 0.37409(12) 0.72228(10) 0.75980(13) 0.0378(5) Uani 1 1 d . . .
H33 H 0.4095 0.6895 0.7650 0.045 Uiso 1 1 calc R . .
C34 C 0.30316(11) 0.71544(9) 0.69774(13) 0.0330(5) Uani 1 1 d . . .
C35 C 0.28190(12) 0.65616(9) 0.63838(13) 0.0362(5) Uani 1 1 d . . .
H35 H 0.2273 0.6523 0.6231 0.043 Uiso 1 1 calc R . .
C36 C 0.25896(17) 0.61511(12) 0.49108(16) 0.0674(8) Uani 1 1 d . . .
H36A H 0.2535 0.6283 0.4316 0.101 Uiso 1 1 calc R . .
H36B H 0.2104 0.6041 0.4934 0.101 Uiso 1 1 calc R . .
H36C H 0.2916 0.5776 0.5077 0.101 Uiso 1 1 calc R . .
C37 C 0.36651(13) 0.68181(11) 0.55462(16) 0.0497(6) Uani 1 1 d . . .
H37A H 0.3946 0.6417 0.5636 0.075 Uiso 1 1 calc R . .
H37B H 0.3909 0.7115 0.6026 0.075 Uiso 1 1 calc R . .
H37C H 0.3643 0.7012 0.4992 0.075 Uiso 1 1 calc R . .
C38 C 0.31285(12) 0.59363(9) 0.68681(14) 0.0376(5) Uani 1 1 d . . .
C39 C 0.38663(13) 0.57465(10) 0.70840(15) 0.0458(6) Uani 1 1 d . . .
H39 H 0.4182 0.5989 0.6869 0.055 Uiso 1 1 calc R . .
C40 C 0.41510(14) 0.52115(10) 0.76054(17) 0.0521(6) Uani 1 1 d . . .
H40 H 0.4653 0.5092 0.7736 0.063 Uiso 1 1 calc R . .
C41 C 0.37063(15) 0.48565(10) 0.79305(17) 0.0541(7) Uani 1 1 d . . .
H41 H 0.3902 0.4501 0.8304 0.065 Uiso 1 1 calc R . .
C42 C 0.29705(15) 0.50243(11) 0.77067(17) 0.0546(7) Uani 1 1 d . . .
H42 H 0.2662 0.4774 0.7922 0.066 Uiso 1 1 calc R . .
C43 C 0.26684(13) 0.55525(10) 0.71728(15) 0.0450(6) Uani 1 1 d . . .
C44 C 0.18540(13) 0.56882(12) 0.69329(18) 0.0572(7) Uani 1 1 d . . .
H44A H 0.1656 0.5419 0.7298 0.069 Uiso 1 1 calc R . .
H44B H 0.1787 0.6143 0.7062 0.069 Uiso 1 1 calc R . .
C45 C 0.06731(16) 0.57793(15) 0.5774(3) 0.0975(12) Uani 1 1 d . . .
H45A H 0.0423 0.5525 0.6091 0.146 Uiso 1 1 calc R . .
H45B H 0.0414 0.5728 0.5144 0.146 Uiso 1 1 calc R . .
H45C H 0.0671 0.6233 0.5931 0.146 Uiso 1 1 calc R . .
C46 C 0.14511(18) 0.48726(13) 0.5794(2) 0.0926(11) Uani 1 1 d . . .
H46A H 0.1216 0.4621 0.6130 0.139 Uiso 1 1 calc R . .
H46B H 0.1966 0.4735 0.5945 0.139 Uiso 1 1 calc R . .
H46C H 0.1185 0.4806 0.5169 0.139 Uiso 1 1 calc R . .
C47 C 0.31504(16) 0.83913(13) 0.42363(17) 0.0637(7) Uani 1 1 d . . .
H47A H 0.2845 0.8738 0.3872 0.076 Uiso 1 1 calc R . .
H47B H 0.3117 0.8009 0.3865 0.076 Uiso 1 1 calc R . .
C48 C 0.39347(18) 0.86029(17) 0.4652(2) 0.0869(10) Uani 1 1 d . . .
H48A H 0.4076 0.8902 0.4268 0.104 Uiso 1 1 calc R . .
H48B H 0.4275 0.8231 0.4790 0.104 Uiso 1 1 calc R . .
C49 C 0.3940(2) 0.89366(15) 0.5475(2) 0.0958(11) Uani 1 1 d . . .
H49A H 0.4426 0.8887 0.5948 0.115 Uiso 1 1 calc R . .
H49B H 0.3832 0.9400 0.5368 0.115 Uiso 1 1 calc R . .
C50 C 0.33412(16) 0.86069(13) 0.57103(17) 0.0657(8) Uani 1 1 d . . .
H50A H 0.3560 0.8320 0.6218 0.079 Uiso 1 1 calc R . .
H50B H 0.3027 0.8927 0.5860 0.079 Uiso 1 1 calc R . .
C51 C 0.0926(3) 0.6994(3) 0.3665(3) 0.165(2) Uani 1 1 d . . .
H51A H 0.0856 0.6894 0.4222 0.198 Uiso 1 1 calc R . .
H51B H 0.0994 0.6588 0.3389 0.198 Uiso 1 1 calc R . .
C52 C 0.0287(3) 0.7359(5) 0.3075(5) 0.237(4) Uani 1 1 d . . .
H52A H 0.0085 0.7137 0.2506 0.285 Uiso 1 1 calc R . .
H52B H -0.0106 0.7380 0.3331 0.285 Uiso 1 1 calc R . .
C53 C 0.0503(3) 0.7970(3) 0.2954(5) 0.212(4) Uani 1 1 d . . .
H53A H 0.0342 0.8283 0.3306 0.254 Uiso 1 1 calc R . .
H53B H 0.0290 0.8095 0.2332 0.254 Uiso 1 1 calc R . .
C54 C 0.13192(18) 0.7945(2) 0.3247(2) 0.0998(12) Uani 1 1 d . . .
H54A H 0.1481 0.7896 0.2739 0.120 Uiso 1 1 calc R . .
H54B H 0.1537 0.8344 0.3560 0.120 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
Li1 O2 1.944(4) . ?
Li1 O1 1.954(4) . ?
Li1 N1 2.152(4) . ?
Li1 P1 2.518(4) . ?
P1 C2 1.808(2) . ?
P1 C1 1.866(2) . ?
N1 C10 1.478(3) . ?
N1 C9 1.480(3) . ?
N1 C8 1.509(3) . ?
N2 C19 1.464(3) . ?
N2 C18 1.471(3) . ?
N2 C17 1.474(3) . ?
O1 C20 1.437(3) . ?
O1 C23 1.446(3) . ?
O2 C27 1.441(3) . ?
O2 C24 1.445(3) . ?
C2 C3 1.427(3) . ?
C2 C7 1.431(3) . ?
C3 C4 1.375(3) . ?
C4 C5 1.383(3) . ?
C5 C6 1.397(3) . ?
C6 C7 1.389(3) . ?
C7 C8 1.537(3) . ?
C8 C11 1.531(3) . ?
C11 C12 1.397(3) . ?
C11 C16 1.420(3) . ?
C12 C13 1.393(3) . ?
C13 C14 1.377(4) . ?
C14 C15 1.379(4) . ?
C15 C16 1.401(3) . ?
C16 C17 1.512(3) . ?
C20 C21 1.494(4) . ?
C21 C22 1.425(5) . ?
C22 C23 1.398(5) . ?
C24 C25 1.487(3) . ?
C25 C26 1.510(4) . ?
C26 C27 1.496(4) . ?
Li2 O4 1.953(4) . ?
Li2 O3 1.968(4) . ?
Li2 N3 2.164(4) . ?
Li2 P2 2.522(4) . ?
P2 C29 1.809(2) . ?
P2 C28 1.869(3) . ?
N3 C37 1.467(3) . ?
N3 C36 1.480(3) . ?
N3 C35 1.506(3) . ?
N4 C45 1.453(3) . ?
N4 C46 1.476(3) . ?
N4 C44 1.477(3) . ?
O3 C47 1.439(3) . ?
O3 C50 1.448(3) . ?
O4 C54 1.413(4) . ?
O4 C51 1.428(4) . ?
C29 C30 1.418(3) . ?
C29 C34 1.435(3) . ?
C30 C31 1.371(3) . ?
C31 C32 1.386(3) . ?
C32 C33 1.395(3) . ?
C33 C34 1.397(3) . ?
C34 C35 1.536(3) . ?
C35 C38 1.533(3) . ?
C38 C39 1.401(3) . ?
C38 C43 1.412(3) . ?
C39 C40 1.394(3) . ?
C40 C41 1.376(3) . ?
C41 C42 1.384(3) . ?
C42 C43 1.399(3) . ?
C43 C44 1.510(3) . ?
C47 C48 1.494(4) . ?
C48 C49 1.514(4) . ?
C49 C50 1.509(4) . ?
C51 C52 1.482(8) . ?
C52 C53 1.377(9) . ?
C53 C54 1.480(6) . ?
