#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:14:16 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179318 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/15/4321507.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_4321507
loop_
_publ_author_name
'Timothy J. Boyle'
'Dawn M. Pedrotty'
'Todd M. Alam'
'Sara C. Vick'
'Mark A. Rodriguez'
_publ_section_title
;
 Structural Diversity in Solvated Lithium Aryloxides. Syntheses,
 Characterization, and Structures of [Li(OAr)(THF)x]n and [Li(OAr)(py)x]2
 Complexes Where OAr = OC6H5, OC6H4(2-Me), OC6H3(2,6-(Me))2, OC6H4(2-Pri),
 OC6H3(2,6-(Pri))2, OC6H4(2-But), OC6H3(2,6-(But))2
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5133
_journal_page_last               5146
_journal_paper_doi               10.1021/ic000432a
_journal_volume                  39
_journal_year                    2000
_chemical_formula_sum            'C36 H58 Li2 N0 O4'
_chemical_formula_weight         568.70
_chemical_name_common            ' [Li(DBP)(THF)]2'
_chemical_name_systematic
; 
 ? 
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.993(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.483(3)
_cell_length_b                   14.693(4)
_cell_length_c                   20.207(5)
_cell_measurement_reflns_used    106
_cell_measurement_temperature    168(2)
_cell_volume                     3525.0(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      168(2)
_diffrn_measured_fraction_theta_full 0.925
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0767
_diffrn_reflns_av_sigmaI/netI    0.1225
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            22139
_diffrn_reflns_theta_full        28.51
_diffrn_reflns_theta_max         28.51
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.072
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       square
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          .5mm
_exptl_crystal_size_mid          .4mm
_exptl_crystal_size_min          .3mm
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.833
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         8264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.833
_refine_ls_R_factor_all          0.1714
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0801P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1673
_reflns_number_gt                3188
_reflns_number_total             8264
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic000432a_7.cif
_cod_data_source_block           dmtp022
_cod_original_cell_volume        3524.9(15)
_cod_database_code               4321507
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.4532(4) 1.0214(3) 0.0408(2) 0.0533(11) Uani 1 1 d . . .
Li2 Li 0.0115(4) 0.5746(3) 0.0253(2) 0.0502(11) Uani 1 1 d . . .
C1 C 0.65307(18) 0.89638(16) 0.09695(11) 0.0369(6) Uani 1 1 d . . .
C2 C 0.75699(19) 0.93544(15) 0.13970(12) 0.0417(6) Uani 1 1 d . . .
C3 C 0.8349(2) 0.87874(18) 0.18447(13) 0.0499(7) Uani 1 1 d . . .
H3 H 0.9035 0.9043 0.2130 0.060 Uiso 1 1 calc R A 1
C4 C 0.8170(2) 0.78700(17) 0.18932(13) 0.0519(7) Uani 1 1 d . . .
H4 H 0.8728 0.7500 0.2203 0.062 Uiso 1 1 calc R B 1
C5 C 0.7173(2) 0.74924(16) 0.14867(13) 0.0467(6) Uani 1 1 d . . .
H5 H 0.7049 0.6859 0.1525 0.056 Uiso 1 1 calc R C 1
C6 C 0.63458(18) 0.80099(15) 0.10234(11) 0.0371(6) Uani 1 1 d . . .
C7 C 0.7802(2) 1.03847(16) 0.13991(13) 0.0498(7) Uani 1 1 d . . .
C8 C 0.8985(2) 1.06375(18) 0.18852(17) 0.0798(10) Uani 1 1 d . . .
H8A H 0.9104 1.1294 0.1858 0.120 Uiso 1 1 calc R D 1
H8B H 0.9557 1.0307 0.1741 0.120 Uiso 1 1 calc R D 1
H8C H 0.9043 1.0472 0.2365 0.120 Uiso 1 1 calc R D 1
C9 C 0.6952(2) 1.09080(17) 0.16720(14) 0.0599(8) Uani 1 1 d . . .
H9A H 0.6183 1.0766 0.1381 0.090 Uiso 1 1 calc R E 1
H9B H 0.7085 1.1564 0.1655 0.090 Uiso 1 1 calc R E 1
H9C H 0.7047 1.0726 0.2153 0.090 Uiso 1 1 calc R E 1
C10 C 0.7760(2) 1.07270(17) 0.06738(15) 0.0639(8) Uani 1 1 d . . .
H10A H 0.7003 1.0632 0.0349 0.096 Uiso 1 1 calc R F 1
H10B H 0.8309 1.0390 0.0511 0.096 Uiso 1 1 calc R F 1
H10C H 0.7943 1.1377 0.0698 0.096 Uiso 1 1 calc R F 1
C11 C 0.52377(19) 0.75469(16) 0.06036(12) 0.0408(6) Uani 1 1 d . . .
C12 C 0.4262(2) 0.79240(18) 0.08335(13) 0.0540(7) Uani 1 1 d . . .
H12A H 0.4389 0.7778 0.1325 0.081 Uiso 1 1 calc R G 1
H12B H 0.3553 0.7649 0.0551 0.081 Uiso 1 1 calc R G 1
H12C H 0.4222 0.8586 0.0771 0.081 Uiso 1 1 calc R G 1
C13 C 0.4997(2) 0.76841(17) -0.01837(12) 0.0500(7) Uani 1 1 d . . .
H13A H 0.4830 0.8327 -0.0300 0.075 Uiso 1 1 calc R H 1
H13B H 0.4350 0.7311 -0.0437 0.075 Uiso 1 1 calc R H 1
H13C H 0.5659 0.7502 -0.0315 0.075 Uiso 1 1 calc R H 1
C14 C 0.5267(2) 0.65107(16) 0.07243(14) 0.0574(8) Uani 1 1 d . . .
H14A H 0.5918 0.6250 0.0618 0.086 Uiso 1 1 calc R I 1
H14B H 0.4574 0.6237 0.0421 0.086 Uiso 1 1 calc R I 1
H14C H 0.5330 0.6387 0.1211 0.086 Uiso 1 1 calc R I 1
C15 C 0.07320(19) 0.41007(14) 0.12338(11) 0.0343(5) Uani 1 1 d . . .
C16 C 0.18784(19) 0.38196(15) 0.14990(11) 0.0364(6) Uani 1 1 d . . .
C17 C 0.2154(2) 0.31826(16) 0.20368(12) 0.0472(7) Uani 1 1 d . . .
H17 H 0.2910 0.2974 0.2207 0.057 Uiso 1 1 calc R J 1
C18 C 0.1376(2) 0.28415(16) 0.23322(13) 0.0522(7) Uani 1 1 d . . .
H18 H 0.1590 0.2394 0.2688 0.063 Uiso 1 1 calc R K 1
C19 C 0.0290(2) 0.31580(15) 0.21039(12) 0.0441(6) Uani 1 1 d . . .
H19 H -0.0238 0.2939 0.2318 0.053 Uiso 1 1 calc R L 1
C20 C -0.00621(19) 0.37905(15) 0.15682(11) 0.0365(6) Uani 1 1 d . . .
C21 C 0.27948(19) 0.42277(17) 0.12210(12) 0.0463(6) Uani 1 1 d . . .
C22 C 0.3972(2) 0.3861(2) 0.16103(14) 0.0674(8) Uani 1 1 d . . .
H22A H 0.4144 0.3982 0.2109 0.101 Uiso 1 1 calc R M 1
H22B H 0.4532 0.4163 0.1436 0.101 Uiso 1 1 calc R M 1
H22C H 0.3993 0.3203 0.1534 0.101 Uiso 1 1 calc R M 1
C23 C 0.2844(2) 0.52634(17) 0.13312(13) 0.0554(7) Uani 1 1 d . . .
H23A H 0.2092 0.5523 0.1121 0.083 Uiso 1 1 calc R N 1
H23B H 0.3370 0.5530 0.1112 0.083 Uiso 1 1 calc R N 1
H23C H 0.3102 0.5397 0.1831 0.083 Uiso 1 1 calc R N 1
C24 C 0.2587(2) 0.40133(18) 0.04451(12) 0.0538(7) Uani 1 1 d . . .
H24A H 0.2518 0.3354 0.0373 0.081 Uiso 1 1 calc R O 1
H24B H 0.3220 0.4240 0.0302 0.081 Uiso 1 1 calc R O 1
H24C H 0.1890 0.4310 0.0167 0.081 Uiso 1 1 calc R O 1
C25 C -0.12822(19) 0.41496(16) 0.13542(12) 0.0428(6) Uani 1 1 d . . .
C26 C -0.1956(2) 0.37721(19) 0.18251(15) 0.0641(8) Uani 1 1 d . . .
H26A H -0.1578 0.3946 0.2309 0.096 Uiso 1 1 calc R P 1
H26B H -0.1995 0.3107 0.1789 0.096 Uiso 1 1 calc R P 1
H26C H -0.2720 0.4025 0.1675 0.096 Uiso 1 1 calc R P 1
C27 C -0.1928(2) 0.38461(17) 0.06053(13) 0.0554(7) Uani 1 1 d . . .
H27A H -0.2708 0.4063 0.0481 0.083 Uiso 1 1 calc R Q 1
H27B H -0.1924 0.3180 0.0578 0.083 Uiso 1 1 calc R Q 1
H27C H -0.1564 0.4102 0.0282 0.083 Uiso 1 1 calc R Q 1
C28 C -0.1300(2) 0.51932(16) 0.14143(12) 0.0487(7) Uani 1 1 d . . .
H28A H -0.0847 0.5462 0.1146 0.073 Uiso 1 1 calc R R 1
H28B H -0.0986 0.5370 0.1904 0.073 Uiso 1 1 calc R R 1
H28C H -0.2077 0.5412 0.1232 0.073 Uiso 1 1 calc R R 1
C29 C 0.0744(3) 0.73329(18) 0.12275(14) 0.0743(10) Uani 1 1 d . . .
H29A H 0.1476 0.7040 0.1466 0.089 Uiso 1 1 calc R S 1
H29B H 0.0229 0.7230 0.1507 0.089 Uiso 1 1 calc R S 1
C30 C 0.0900(3) 0.83246(19) 0.11391(16) 0.0807(10) Uani 1 1 d . . .
H30A H 0.0737 0.8678 0.1514 0.097 Uiso 1 1 calc R T 1
H30B H 0.1680 0.8457 0.1144 0.097 Uiso 1 1 calc R T 1
C31 C 0.0091(3) 0.85451(19) 0.04602(16) 0.0833(11) Uani 1 1 d . . .
H31A H -0.0613 0.8790 0.0518 0.100 Uiso 1 1 calc R U 1
H31B H 0.0411 0.9005 0.0216 0.100 Uiso 1 1 calc R U 1
C32 C -0.0127(4) 0.77118(19) 0.00742(18) 0.1156(16) Uani 1 1 d . . .
H32A H 0.0261 0.7716 -0.0286 0.139 Uiso 1 1 calc R V 1
H32B H -0.0945 0.7644 -0.0161 0.139 Uiso 1 1 calc R V 1
C33 C 0.3965(3) 1.0208(3) 0.17379(15) 0.1073(14) Uani 1 1 d . . .
H33A H 0.4678 1.0481 0.2033 0.129 Uiso 1 1 calc R W 1
H33B H 0.4041 0.9537 0.1764 0.129 Uiso 1 1 calc R W 1
C34 C 0.3031(4) 1.0496(2) 0.19782(18) 0.1050(14) Uani 1 1 d . . .
H34A H 0.3261 1.1009 0.2310 0.126 Uiso 1 1 calc R X 1
H34B H 0.2772 0.9988 0.2212 0.126 Uiso 1 1 calc R X 1
C35 C 0.2125(3) 1.0783(2) 0.1343(2) 0.0897(11) Uani 1 1 d . . .
H35A H 0.1610 1.0272 0.1145 0.108 Uiso 1 1 calc R Y 1
H35B H 0.1683 1.1294 0.1445 0.108 Uiso 1 1 calc R Y 1
C36 C 0.2747(2) 1.1068(2) 0.08706(15) 0.0686(9) Uani 1 1 d . . .
H36A H 0.2283 1.0979 0.0380 0.082 Uiso 1 1 calc R Z 1
H36B H 0.2959 1.1718 0.0942 0.082 Uiso 1 1 calc R Z 1
O1 O 0.57612(12) 0.94880(10) 0.05264(7) 0.0398(4) Uani 1 1 d . . .
O2 O 0.04015(12) 0.46416(10) 0.06741(7) 0.0369(4) Uani 1 1 d . . .
O3 O 0.02761(14) 0.69700(10) 0.05442(8) 0.0536(5) Uani 1 1 d . . .
O4 O 0.37287(14) 1.05071(13) 0.10345(8) 0.0624(5) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Li1 O1 99.5(2) . 3_675 ?
O1 Li1 O4 130.2(2) . . ?
O1 Li1 O4 130.2(2) 3_675 . ?
O1 Li1 Li1 50.45(16) . 3_675 ?
O1 Li1 Li1 49.00(16) 3_675 3_675 ?
O4 Li1 Li1 176.9(4) . 3_675 ?
O2 Li2 O2 98.86(19) . 3_565 ?
O2 Li2 O3 136.1(2) . . ?
O2 Li2 O3 125.0(2) 3_565 . ?
O2 Li2 Li2 50.43(15) . 3_565 ?
O2 Li2 Li2 48.43(15) 3_565 3_565 ?
O3 Li2 Li2 173.3(3) . 3_565 ?
O1 C1 C6 121.09(19) . . ?
O1 C1 C2 120.1(2) . . ?
C6 C1 C2 118.85(19) . . ?
C3 C2 C1 118.3(2) . . ?
C3 C2 C7 119.7(2) . . ?
C1 C2 C7 121.86(19) . . ?
C4 C3 C2 122.7(2) . . ?
C5 C4 C3 119.2(2) . . ?
C4 C5 C6 121.9(2) . . ?
C5 C6 C1 119.0(2) . . ?
C5 C6 C11 119.0(2) . . ?
C1 C6 C11 121.99(19) . . ?
C10 C7 C2 111.6(2) . . ?
C10 C7 C8 105.8(2) . . ?
C2 C7 C8 112.3(2) . . ?
C10 C7 C9 110.7(2) . . ?
C2 C7 C9 109.9(2) . . ?
C8 C7 C9 106.3(2) . . ?
C12 C11 C13 110.25(19) . . ?
C12 C11 C14 106.9(2) . . ?
C13 C11 C14 106.30(19) . . ?
C12 C11 C6 109.61(19) . . ?
C13 C11 C6 111.52(19) . . ?
C14 C11 C6 112.08(19) . . ?
O2 C15 C16 120.1(2) . . ?
O2 C15 C20 120.6(2) . . ?
C16 C15 C20 119.4(2) . . ?
C17 C16 C15 117.7(2) . . ?
C17 C16 C21 120.8(2) . . ?
C15 C16 C21 121.4(2) . . ?
C18 C17 C16 122.9(2) . . ?
C19 C18 C17 119.0(2) . . ?
C18 C19 C20 122.0(2) . . ?
C19 C20 C15 118.7(2) . . ?
C19 C20 C25 119.6(2) . . ?
C15 C20 C25 121.7(2) . . ?
C23 C21 C22 106.5(2) . . ?
C23 C21 C16 109.5(2) . . ?
C22 C21 C16 112.2(2) . . ?
C23 C21 C24 109.7(2) . . ?
C22 C21 C24 106.5(2) . . ?
C16 C21 C24 112.36(19) . . ?
C28 C25 C27 110.44(19) . . ?
C28 C25 C20 110.84(18) . . ?
C27 C25 C20 110.34(19) . . ?
C28 C25 C26 106.5(2) . . ?
C27 C25 C26 106.2(2) . . ?
C20 C25 C26 112.4(2) . . ?
O3 C29 C30 106.2(2) . . ?
C31 C30 C29 104.5(2) . . ?
C32 C31 C30 106.3(2) . . ?
C31 C32 O3 108.7(3) . . ?
O4 C33 C34 107.6(3) . . ?
C33 C34 C35 105.6(3) . . ?
C36 C35 C34 103.2(3) . . ?
O4 C36 C35 105.9(2) . . ?
C1 O1 Li1 145.74(19) . . ?
C1 O1 Li1 133.69(19) . 3_675 ?
Li1 O1 Li1 80.5(2) . 3_675 ?
C15 O2 Li2 153.00(18) . . ?
C15 O2 Li2 125.85(17) . 3_565 ?
Li2 O2 Li2 81.14(19) . 3_565 ?
C29 O3 C32 108.2(2) . . ?
C29 O3 Li2 129.2(2) . . ?
C32 O3 Li2 122.5(2) . . ?
C33 O4 C36 107.9(2) . . ?
C33 O4 Li1 127.3(2) . . ?
C36 O4 Li1 124.82(19) . . ?
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 O1 1.822(4) . ?
Li1 O1 1.862(4) 3_675 ?
Li1 O4 1.891(5) . ?
Li1 Li1 2.382(9) 3_675 ?
Li2 O2 1.816(4) . ?
Li2 O2 1.872(4) 3_565 ?
Li2 O3 1.883(4) . ?
Li2 Li2 2.399(8) 3_565 ?
C1 O1 1.337(2) . ?
C1 C6 1.430(3) . ?
C1 C2 1.437(3) . ?
C2 C3 1.383(3) . ?
C2 C7 1.541(3) . ?
C3 C4 1.375(3) . ?
C4 C5 1.379(3) . ?
C5 C6 1.387(3) . ?
C6 C11 1.540(3) . ?
C7 C10 1.535(4) . ?
C7 C8 1.545(3) . ?
C7 C9 1.544(4) . ?
C11 C12 1.535(3) . ?
C11 C13 1.538(3) . ?
C11 C14 1.540(3) . ?
C15 O2 1.339(2) . ?
C15 C16 1.425(3) . ?
C15 C20 1.435(3) . ?
C16 C17 1.394(3) . ?
C16 C21 1.543(3) . ?
C17 C18 1.382(3) . ?
C18 C19 1.371(3) . ?
C19 C20 1.391(3) . ?
C20 C25 1.542(3) . ?
C21 C23 1.536(3) . ?
C21 C22 1.535(3) . ?
C21 C24 1.541(3) . ?
C25 C28 1.539(3) . ?
C25 C27 1.544(3) . ?
C25 C26 1.554(3) . ?
C29 O3 1.426(3) . ?
C29 C30 1.488(4) . ?
C30 C31 1.466(4) . ?
C31 C32 1.432(4) . ?
C32 O3 1.431(3) . ?
C33 O4 1.429(3) . ?
C33 C34 1.457(5) . ?
C34 C35 1.485(5) . ?
C35 C36 1.466(4) . ?
C36 O4 1.428(3) . ?
O1 Li1 1.862(4) 3_675 ?
O2 Li2 1.872(4) 3_565 ?
