#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:58:54 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178927 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/56/4115651.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_4115651
loop_
_publ_author_name
'Hans J. Reich'
'Wayne S. Goldenberg'
'Birgir Ö. Gudmundsson'
'Aaron W. Sanders'
'Klaus J. Kulicke'
'Katya Simon'
'Ilia A. Guzei'
_publ_section_title
;
 Amine-Chelated Aryllithium Reagents Structure and Dynamics
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8067
_journal_page_last               8079
_journal_paper_doi               10.1021/ja010489b
_journal_volume                  123
_journal_year                    2001
_chemical_formula_sum            'C30 H48 Li2 N2 O2'
_chemical_formula_weight         482.58
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                117.115(2)
_cell_angle_beta                 102.521(2)
_cell_angle_gamma                98.701(2)
_cell_formula_units_Z            1
_cell_length_a                   8.8594(9)
_cell_length_b                   9.8398(10)
_cell_length_c                   10.4018(11)
_cell_measurement_temperature    173(2)
_cell_volume                     754.58(14)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3067
_diffrn_reflns_theta_full        26.43
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.9867
_exptl_absorpt_correction_T_min  0.9736
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.062
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3067
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1497
_refine_ls_wR_factor_ref         0.1616
_reflns_number_gt                2120
_reflns_number_total             3067
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja010489b.cif
_cod_data_source_block           rei02
_cod_original_cell_volume        754.58(13)
_cod_database_code               4115651
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
O1 O 0.18600(14) -0.22809(13) -0.06532(13) 0.0534(4) Uani 1 1 d .
N1 N 0.22886(15) 0.06220(14) 0.28224(14) 0.0346(3) Uani 1 1 d .
Li1 Li 0.0950(3) -0.0602(3) 0.0439(3) 0.0362(6) Uani 1 1 d .
C1 C 0.3514(2) 0.42659(19) 0.2754(2) 0.0464(4) Uani 1 1 d .
H1 H 0.3961 0.4949 0.3830 0.056 Uiso 1 1 calc R
C2 C 0.3898(2) 0.4781(2) 0.1793(2) 0.0558(5) Uani 1 1 d .
H2 H 0.4577 0.5826 0.2204 0.067 Uiso 1 1 calc R
C3 C 0.3285(2) 0.3763(2) 0.0245(2) 0.0522(5) Uani 1 1 d .
H3 H 0.3570 0.4083 -0.0426 0.063 Uiso 1 1 calc R
C4 C 0.22446(19) 0.2262(2) -0.03375(19) 0.0446(4) Uani 1 1 d .
H4 H 0.1839 0.1583 -0.1416 0.054 Uiso 1 1 calc R
C5 C 0.17497(18) 0.16751(17) 0.05528(17) 0.0352(4) Uani 1 1 d .
C6 C 0.24740(18) 0.27494(17) 0.21469(17) 0.0360(4) Uani 1 1 d .
C7 C 0.2099(2) 0.22261(18) 0.32355(17) 0.0398(4) Uani 1 1 d .
H7A H 0.2830 0.3008 0.4285 0.048 Uiso 1 1 calc R
H7B H 0.0977 0.2214 0.3225 0.048 Uiso 1 1 calc R
C8 C 0.39734(19) 0.0655(2) 0.2948(2) 0.0460(4) Uani 1 1 d .
H8A H 0.4289 0.0974 0.2257 0.069 Uiso 1 1 calc R
H8B H 0.4092 -0.0408 0.2671 0.069 Uiso 1 1 calc R
H8C H 0.4666 0.1422 0.4001 0.069 Uiso 1 1 calc R
C9 C 0.1670(2) 0.0005(2) 0.37297(18) 0.0445(4) Uani 1 1 d .
H9 H 0.0544 0.0091 0.3617 0.053 Uiso 1 1 calc R
C10 C 0.2601(2) 0.0949(3) 0.5445(2) 0.0600(5) Uani 1 1 d .
H10A H 0.3716 0.0894 0.5612 0.090 Uiso 1 1 calc R
H10B H 0.2084 0.0493 0.5959 0.090 Uiso 1 1 calc R
H10C H 0.2598 0.2065 0.5861 0.090 Uiso 1 1 calc R
C11 C 0.1546(3) -0.1751(2) 0.3077(2) 0.0624(6) Uani 1 1 d .
H11A H 0.0971 -0.2330 0.1975 0.094 Uiso 1 1 calc R
H11B H 0.0956 -0.2174 0.3572 0.094 Uiso 1 1 calc R
H11C H 0.2633 -0.1883 0.3260 0.094 Uiso 1 1 calc R
C12 C 0.1104(2) -0.3974(2) -0.1412(2) 0.0547(5) Uani 1 1 d .
H12A H -0.0045 -0.4193 -0.1471 0.066 Uiso 1 1 calc R
H12B H 0.1661 -0.4446 -0.0860 0.066 Uiso 1 1 calc R
C13 C 0.1249(3) -0.4637(3) -0.2970(3) 0.0858(8) Uani 1 1 d .
H13A H 0.0177 -0.5002 -0.3743 0.103 Uiso 1 1 calc R
H13B H 0.1695 -0.5556 -0.3214 0.103 Uiso 1 1 calc R
C14 C 0.2366(2) -0.3322(2) -0.2972(2) 0.0665(6) Uani 1 1 d .
H14A H 0.1765 -0.2921 -0.3577 0.080 Uiso 1 1 calc R
H14B H 0.3220 -0.3694 -0.3394 0.080 Uiso 1 1 calc R
C15 C 0.3076(2) -0.2051(2) -0.1306(2) 0.0629(6) Uani 1 1 d .
H15A H 0.4090 -0.2183 -0.0818 0.075 Uiso 1 1 calc R
H15B H 0.3304 -0.0974 -0.1183 0.075 Uiso 1 1 calc R
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
C15 O1 C12 107.35(13) . .
C15 O1 Li1 122.60(13) . .
C12 O1 Li1 126.40(13) . .
C8 N1 C7 109.75(12) . .
C8 N1 C9 112.80(12) . .
C7 N1 C9 111.85(12) . .
C8 N1 Li1 106.94(12) . .
C7 N1 Li1 98.62(11) . .
C9 N1 Li1 115.89(11) . .
O1 Li1 N1 109.03(13) . .
O1 Li1 C5 117.50(13) . .
N1 Li1 C5 86.39(10) . .
O1 Li1 C5 106.14(12) . 2
N1 Li1 C5 124.53(13) . 2
C5 Li1 C5 113.05(11) . 2
O1 Li1 Li1 131.91(18) . 2
N1 Li1 Li1 117.72(16) . 2
C5 Li1 Li1 57.81(11) . 2
C5 Li1 Li1 55.24(10) 2 2
O1 Li1 C7 134.74(12) . .
N1 Li1 C7 31.83(6) . .
C5 Li1 C7 59.70(8) . .
C5 Li1 C7 116.17(11) 2 .
Li1 Li1 C7 87.43(13) 2 .
C2 C1 C6 120.29(15) . .
C3 C2 C1 119.18(15) . .
C2 C3 C4 119.63(16) . .
C3 C4 C5 124.67(16) . .
C4 C5 C6 113.34(13) . .
C4 C5 Li1 139.40(13) . .
C6 C5 Li1 102.42(12) . .
C4 C5 Li1 108.06(12) . 2
C6 C5 Li1 119.58(12) . 2
Li1 C5 Li1 66.95(11) . 2
C1 C6 C5 122.80(14) . .
C1 C6 C7 118.65(13) . .
C5 C6 C7 118.55(13) . .
N1 C7 C6 112.10(12) . .
N1 C7 Li1 49.55(8) . .
C6 C7 Li1 77.01(9) . .
N1 C9 C11 111.11(14) . .
N1 C9 C10 114.92(13) . .
C11 C9 C10 110.66(15) . .
O1 C12 C13 105.33(16) . .
C12 C13 C14 107.12(17) . .
C13 C14 C15 103.60(18) . .
O1 C15 C14 104.59(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C15 1.434(2) .
O1 C12 1.442(2) .
O1 Li1 1.939(3) .
N1 C8 1.4638(19) .
N1 C7 1.4824(19) .
N1 C9 1.4849(19) .
N1 Li1 2.139(3) .
Li1 C5 2.186(3) .
Li1 C5 2.252(3) 2
Li1 Li1 2.449(5) 2
Li1 C7 2.779(3) .
C1 C2 1.389(3) .
C1 C6 1.395(2) .
C2 C3 1.370(3) .
C3 C4 1.389(2) .
C4 C5 1.403(2) .
C5 C6 1.419(2) .
C5 Li1 2.252(3) 2
C6 C7 1.517(2) .
C9 C11 1.517(2) .
C9 C10 1.532(2) .
C12 C13 1.490(3) .
C13 C14 1.507(3) .
C14 C15 1.509(3) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C15 O1 Li1 N1 -92.78(18) . .
C12 O1 Li1 N1 111.54(16) . .
C15 O1 Li1 C5 3.2(2) . .
C12 O1 Li1 C5 -152.46(14) . .
C15 O1 Li1 C5 130.83(15) . 2
C12 O1 Li1 C5 -24.9(2) . 2
C15 O1 Li1 Li1 73.4(3) . 2
C12 O1 Li1 Li1 -82.3(3) . 2
C15 O1 Li1 C7 -70.2(2) . .
C12 O1 Li1 C7 134.08(17) . .
C8 N1 Li1 O1 35.11(16) . .
C7 N1 Li1 O1 148.91(12) . .
C9 N1 Li1 O1 -91.62(15) . .
C8 N1 Li1 C5 -82.77(12) . .
C7 N1 Li1 C5 31.02(11) . .
C9 N1 Li1 C5 150.50(11) . .
C8 N1 Li1 C5 161.58(14) . 2
C7 N1 Li1 C5 -84.63(16) . 2
C9 N1 Li1 C5 34.8(2) . 2
C8 N1 Li1 Li1 -133.27(17) . 2
C7 N1 Li1 Li1 -19.5(2) . 2
C9 N1 Li1 Li1 100.00(19) . 2
C8 N1 Li1 C7 -113.79(14) . .
C9 N1 Li1 C7 119.48(15) . .
C6 C1 C2 C3 -2.1(3) . .
C1 C2 C3 C4 2.5(3) . .
C2 C3 C4 C5 0.0(3) . .
C3 C4 C5 C6 -2.5(2) . .
C3 C4 C5 Li1 -152.23(18) . .
C3 C4 C5 Li1 132.39(17) . 2
O1 Li1 C5 C4 33.0(3) . .
N1 Li1 C5 C4 142.59(18) . .
C5 Li1 C5 C4 -91.2(2) 2 .
Li1 Li1 C5 C4 -91.2(2) 2 .
C7 Li1 C5 C4 160.9(2) . .
O1 Li1 C5 C6 -118.68(15) . .
N1 Li1 C5 C6 -9.08(12) . .
C5 Li1 C5 C6 117.11(14) 2 .
Li1 Li1 C5 C6 117.11(14) 2 .
C7 Li1 C5 C6 9.27(9) . .
O1 Li1 C5 Li1 124.21(19) . 2
N1 Li1 C5 Li1 -126.19(15) . 2
C5 Li1 C5 Li1 0.0 2 2
C7 Li1 C5 Li1 -107.84(12) . 2
C2 C1 C6 C5 -0.7(3) . .
C2 C1 C6 C7 179.38(15) . .
C4 C5 C6 C1 2.9(2) . .
Li1 C5 C6 C1 163.22(15) . .
Li1 C5 C6 C1 -126.41(16) 2 .
C4 C5 C6 C7 -177.21(13) . .
Li1 C5 C6 C7 -16.86(16) . .
Li1 C5 C6 C7 53.50(18) 2 .
C8 N1 C7 C6 63.24(16) . .
C9 N1 C7 C6 -170.77(12) . .
Li1 N1 C7 C6 -48.32(14) . .
C8 N1 C7 Li1 111.56(14) . .
C9 N1 C7 Li1 -122.46(14) . .
C1 C6 C7 N1 -131.18(15) . .
C5 C6 C7 N1 48.90(18) . .
C1 C6 C7 Li1 -166.86(15) . .
C5 C6 C7 Li1 13.22(13) . .
O1 Li1 C7 N1 -43.42(17) . .
C5 Li1 C7 N1 -143.44(13) . .
C5 Li1 C7 N1 113.96(15) 2 .
Li1 Li1 C7 N1 162.81(18) 2 .
O1 Li1 C7 C6 91.33(18) . .
N1 Li1 C7 C6 134.75(14) . .
C5 Li1 C7 C6 -8.69(9) . .
C5 Li1 C7 C6 -111.29(13) 2 .
Li1 Li1 C7 C6 -62.43(13) 2 .
C8 N1 C9 C11 -67.59(18) . .
C7 N1 C9 C11 168.11(14) . .
Li1 N1 C9 C11 56.14(18) . .
C8 N1 C9 C10 59.01(19) . .
C7 N1 C9 C10 -65.28(18) . .
Li1 N1 C9 C10 -177.26(14) . .
C15 O1 C12 C13 -28.8(2) . .
Li1 O1 C12 C13 129.92(19) . .
O1 C12 C13 C14 10.0(3) . .
C12 C13 C14 C15 11.0(3) . .
C12 O1 C15 C14 36.0(2) . .
Li1 O1 C15 C14 -123.65(17) . .
C13 C14 C15 O1 -28.2(2) . .
