#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:26:14 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178469 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/90/4029030.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_4029030
loop_
_publ_author_name
'Su, Chicheung'
'Guang, Jie'
'Williard, Paul G.'
_publ_section_title
;
 Structures of Lithium N-Monosubstituted Anilides: Trisolvated Monomer to
 Tetrasolvated Dimer.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1032
_journal_paper_doi               10.1021/jo402498z
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C15 H24 Li N O'
_chemical_formula_weight         241.29
_chemical_name_common            ccs06jun13
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                101.459(15)
_cell_angle_beta                 109.730(15)
_cell_angle_gamma                104.830(16)
_cell_formula_units_Z            2
_cell_length_a                   8.493(3)
_cell_length_b                   9.954(4)
_cell_length_c                   10.417(3)
_cell_measurement_reflns_used    5930
_cell_measurement_temperature    198.(2)
_cell_measurement_theta_max      28.8880
_cell_measurement_theta_min      2.1872
_cell_volume                     761.0(5)
_computing_cell_refinement       'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      198.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16436
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.053
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.214
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3116
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0736P)²+0.1687P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1412
_reflns_number_gt                2513
_reflns_number_total             3116
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo402498z_si_002.cif
_cod_data_source_block           958153
_cod_database_code               4029030
#BEGIN Tags that were not found in dictionaries:
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
C C1 0.4672(2) 0.39935(15) 0.22221(14) 0.0360(3) Uani d . . 1
H H1A 0.5175 0.5053 0.2369 0.043 Uiso calc U R 1
H H1B 0.3525 0.3587 0.1362 0.043 Uiso calc U R 1
C C2 0.5963(2) 0.32647(16) 0.19132(15) 0.0403(4) Uani d . . 1
C C3 0.5232(2) 0.16206(17) 0.16576(19) 0.0535(4) Uani d . . 1
H H3A 0.4097 0.1177 0.0806 0.08 Uiso calc U R 1
H H3B 0.504 0.1447 0.2496 0.08 Uiso calc U R 1
H H3C 0.6091 0.1182 0.1507 0.08 Uiso calc U R 1
C C4 0.6171(3) 0.3556(3) 0.05828(19) 0.0680(6) Uani d . . 1
H H4A 0.701 0.3123 0.038 0.102 Uiso calc U R 1
H H4B 0.6629 0.4614 0.0756 0.102 Uiso calc U R 1
H H4C 0.5008 0.3119 -0.0241 0.102 Uiso calc U R 1
C C5 0.7809(2) 0.39261(18) 0.31698(17) 0.0477(4) Uani d . . 1
H H5A 0.7718 0.3691 0.4018 0.072 Uiso calc U R 1
H H5B 0.8252 0.4991 0.3382 0.072 Uiso calc U R 1
H H5C 0.8637 0.3519 0.2913 0.072 Uiso calc U R 1
C C6 0.27420(18) 0.27626(13) 0.32283(13) 0.0318(3) Uani d . . 1
C C7 0.13236(19) 0.18604(15) 0.18847(15) 0.0395(3) Uani d . . 1
H H7 0.1441 0.1932 0.1023 0.047 Uiso calc U R 1
C C8 -0.0215(2) 0.08858(17) 0.18009(18) 0.0505(4) Uani d . . 1
H H8 -0.1133 0.0314 0.088 0.061 Uiso calc U R 1
C C9 -0.0472(2) 0.07087(18) 0.3003(2) 0.0533(4) Uani d . . 1
H H9 -0.154 0.0024 0.2923 0.064 Uiso calc U R 1
C C10 0.0881(2) 0.15642(18) 0.43360(19) 0.0489(4) Uani d . . 1
H H10 0.074 0.147 0.5184 0.059 Uiso calc U R 1
C C11 0.2434(2) 0.25532(15) 0.44433(15) 0.0386(3) Uani d . . 1
H H11 0.3335 0.3118 0.5373 0.046 Uiso calc U R 1
C C12 0.6850(3) 0.19089(18) 0.5941(2) 0.0639(5) Uani d . . 1
H H12A 0.747 0.166 0.5327 0.077 Uiso calc U R 1
H H12B 0.5545 0.1428 0.5371 0.077 Uiso calc U R 1
C C13 0.7431(3) 0.1434(2) 0.7239(2) 0.0644(5) Uani d . . 1
H H13A 0.774 0.0545 0.7033 0.077 Uiso calc U R 1
H H13B 0.6493 0.1242 0.761 0.077 Uiso calc U R 1
C C14 0.9045(3) 0.2728(2) 0.8272(2) 0.0627(5) Uani d . . 1
H H14A 1.0114 0.2713 0.8093 0.075 Uiso calc U R 1
H H14B 0.9286 0.276 0.9279 0.075 Uiso calc U R 1
C C15 0.8520(2) 0.39935(17) 0.79566(15) 0.0440(4) Uani d . . 1
H H15A 0.7925 0.4316 0.8566 0.053 Uiso calc U R 1
H H15B 0.9583 0.4828 0.8136 0.053 Uiso calc U R 1
Li Li1 0.6272(3) 0.4592(3) 0.5416(2) 0.0383(5) Uani d . . 1
N N1 0.43060(15) 0.38141(11) 0.34629(11) 0.0316(3) Uani d . . 1
O O1 0.73184(15) 0.34650(11) 0.64724(10) 0.0482(3) Uani d . . 1
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N1 C1 C2 . . 115.52(11)
N1 C1 H1A . . 108.4
C2 C1 H1A . . 108.4
N1 C1 H1B . . 108.4
C2 C1 H1B . . 108.4
H1A C1 H1B . . 107.5
C3 C2 C4 . . 110.19(14)
C3 C2 C5 . . 109.01(13)
C4 C2 C5 . . 108.19(14)
C3 C2 C1 . . 110.48(13)
C4 C2 C1 . . 108.07(13)
C5 C2 C1 . . 110.87(12)
C2 C3 H3A . . 109.5
C2 C3 H3B . . 109.5
H3A C3 H3B . . 109.5
C2 C3 H3C . . 109.5
H3A C3 H3C . . 109.5
H3B C3 H3C . . 109.5
C2 C4 H4A . . 109.5
C2 C4 H4B . . 109.5
H4A C4 H4B . . 109.5
C2 C4 H4C . . 109.5
H4A C4 H4C . . 109.5
H4B C4 H4C . . 109.5
C2 C5 H5A . . 109.5
C2 C5 H5B . . 109.5
H5A C5 H5B . . 109.5
C2 C5 H5C . . 109.5
H5A C5 H5C . . 109.5
H5B C5 H5C . . 109.5
N1 C6 C11 . . 117.97(11)
N1 C6 C7 . . 127.59(12)
C11 C6 C7 . . 114.40(13)
N1 C6 Li1 . 2_666 54.91(9)
C11 C6 Li1 . 2_666 83.45(10)
C7 C6 Li1 . 2_666 132.35(11)
C8 C7 C6 . . 121.70(14)
C8 C7 H7 . . 119.2
C6 C7 H7 . . 119.2
C7 C8 C9 . . 122.43(14)
C7 C8 H8 . . 118.8
C9 C8 H8 . . 118.8
C8 C9 C10 . . 117.74(15)
C8 C9 H9 . . 121.1
C10 C9 H9 . . 121.1
C11 C10 C9 . . 120.73(15)
C11 C10 H10 . . 119.6
C9 C10 H10 . . 119.6
C10 C11 C6 . . 123.00(14)
C10 C11 Li1 . 2_666 138.62(12)
C6 C11 Li1 . 2_666 65.40(9)
C10 C11 H11 . . 118.5
C6 C11 H11 . . 118.5
Li1 C11 H11 2_666 . 69.5
O1 C12 C13 . . 105.54(14)
O1 C12 H12A . . 110.6
C13 C12 H12A . . 110.6
O1 C12 H12B . . 110.6
C13 C12 H12B . . 110.6
H12A C12 H12B . . 108.8
C12 C13 C14 . . 102.34(15)
C12 C13 H13A . . 111.3
C14 C13 H13A . . 111.3
C12 C13 H13B . . 111.3
C14 C13 H13B . . 111.3
H13A C13 H13B . . 109.2
C13 C14 C15 . . 102.63(14)
C13 C14 H14A . . 111.2
C15 C14 H14A . . 111.2
C13 C14 H14B . . 111.2
C15 C14 H14B . . 111.2
H14A C14 H14B . . 109.2
O1 C15 C14 . . 105.60(13)
O1 C15 H15A . . 110.6
C14 C15 H15A . . 110.6
O1 C15 H15B . . 110.6
C14 C15 H15B . . 110.6
H15A C15 H15B . . 108.8
O1 Li1 N1 . . 125.93(13)
O1 Li1 N1 . 2_666 115.81(12)
N1 Li1 N1 . 2_666 105.18(11)
O1 Li1 Li1 . 2_666 147.08(19)
N1 Li1 Li1 . 2_666 53.64(9)
N1 Li1 Li1 2_666 2_666 51.54(9)
O1 Li1 C6 . 2_666 115.12(11)
N1 Li1 C6 . 2_666 118.52(11)
N1 Li1 C6 2_666 2_666 33.39(6)
Li1 Li1 C6 2_666 2_666 71.99(11)
O1 Li1 C11 . 2_666 131.40(12)
N1 Li1 C11 . 2_666 99.49(10)
N1 Li1 C11 2_666 2_666 58.17(7)
Li1 Li1 C11 2_666 2_666 72.17(11)
C6 Li1 C11 2_666 2_666 31.15(5)
C6 N1 C1 . . 118.38(11)
C6 N1 Li1 . . 118.55(11)
C1 N1 Li1 . . 120.42(12)
C6 N1 Li1 . 2_666 91.70(11)
C1 N1 Li1 . 2_666 119.14(11)
Li1 N1 Li1 . 2_666 74.82(11)
C15 O1 C12 . . 109.56(12)
C15 O1 Li1 . . 125.57(11)
C12 O1 Li1 . . 124.48(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.4606(17)
C1 C2 . 1.544(2)
C1 H1A . 0.99
C1 H1B . 0.99
C2 C3 . 1.526(2)
C2 C4 . 1.528(2)
C2 C5 . 1.532(2)
C3 H3A . 0.98
C3 H3B . 0.98
C3 H3C . 0.98
C4 H4A . 0.98
C4 H4B . 0.98
C4 H4C . 0.98
C5 H5A . 0.98
C5 H5B . 0.98
C5 H5C . 0.98
C6 N1 . 1.3737(18)
C6 C11 . 1.4194(19)
C6 C7 . 1.4231(19)
C6 Li1 2_666 2.495(3)
C7 C8 . 1.377(2)
C7 H7 . 0.95
C8 C9 . 1.379(3)
C8 H8 . 0.95
C9 C10 . 1.387(2)
C9 H9 . 0.95
C10 C11 . 1.383(2)
C10 H10 . 0.95
C11 Li1 2_666 2.726(3)
C11 H11 . 0.95
C12 O1 . 1.435(2)
C12 C13 . 1.489(3)
C12 H12A . 0.99
C12 H12B . 0.99
C13 C14 . 1.499(3)
C13 H13A . 0.99
C13 H13B . 0.99
C14 C15 . 1.499(2)
C14 H14A . 0.99
C14 H14B . 0.99
C15 O1 . 1.4302(17)
C15 H15A . 0.99
C15 H15B . 0.99
Li1 O1 . 1.897(2)
Li1 N1 . 1.986(3)
Li1 N1 2_666 2.042(3)
Li1 Li1 2_666 2.448(5)
Li1 C6 2_666 2.495(3)
Li1 C11 2_666 2.726(3)
N1 Li1 2_666 2.043(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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
N1 C1 C2 C3 . . 58.95(16)
N1 C1 C2 C4 . . 179.58(13)
N1 C1 C2 C5 . . -62.02(16)
N1 C6 C7 C8 . . -177.17(13)
C11 C6 C7 C8 . . 0.7(2)
Li1 C6 C7 C8 2_666 . -103.43(18)
C6 C7 C8 C9 . . -0.8(2)
C7 C8 C9 C10 . . 0.5(2)
C8 C9 C10 C11 . . -0.3(2)
C9 C10 C11 C6 . . 0.3(2)
C9 C10 C11 Li1 . 2_666 89.5(2)
N1 C6 C11 C10 . . 177.62(13)
C7 C6 C11 C10 . . -0.5(2)
Li1 C6 C11 C10 2_666 . 133.36(15)
N1 C6 C11 Li1 . 2_666 44.26(11)
C7 C6 C11 Li1 . 2_666 -133.83(13)
O1 C12 C13 C14 . . -32.3(2)
C12 C13 C14 C15 . . 37.5(2)
C13 C14 C15 O1 . . -29.59(19)
C11 C6 N1 C1 . . 177.33(11)
C7 C6 N1 C1 . . -4.86(19)
Li1 C6 N1 C1 2_666 . -124.73(13)
C11 C6 N1 Li1 . . 15.68(17)
C7 C6 N1 Li1 . . -166.51(13)
Li1 C6 N1 Li1 2_666 . 73.62(13)
C11 C6 N1 Li1 . 2_666 -57.93(13)
C7 C6 N1 Li1 . 2_666 119.87(14)
C2 C1 N1 C6 . . -100.02(15)
C2 C1 N1 Li1 . . 61.28(16)
C2 C1 N1 Li1 . 2_666 150.11(12)
C14 C15 O1 C12 . . 9.80(19)
C14 C15 O1 Li1 . . -177.15(15)
C13 C12 O1 C15 . . 14.3(2)
C13 C12 O1 Li1 . . -158.87(16)
N1 Li1 O1 C15 . . -169.11(14)
N1 Li1 O1 C15 2_666 . -33.9(2)
Li1 Li1 O1 C15 2_666 . -92.3(3)
C6 Li1 O1 C15 2_666 . 3.2(2)
C11 Li1 O1 C15 2_666 . 35.3(2)
N1 Li1 O1 C12 . . 2.9(3)
N1 Li1 O1 C12 2_666 . 138.16(17)
Li1 Li1 O1 C12 2_666 . 79.8(3)
C6 Li1 O1 C12 2_666 . 175.26(15)
C11 Li1 O1 C12 2_666 . -152.61(16)
