#------------------------------------------------------------------------------
#$Date: 2016-03-21 15:17:06 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178742 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/53/4085397.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_4085397
loop_
_publ_author_name
'Brendel, Matthias'
'Wenz, Jan'
'Shishkov, Igor V.'
'Rominger, Frank'
'Hofmann, Peter'
_publ_section_title
;
 Lithium Complexes of Neutral Bis-NHC Ligands
;
_journal_issue                   3
_journal_name_full               Organometallics
_journal_page_first              669
_journal_paper_doi               10.1021/om501229b
_journal_volume                  34
_journal_year                    2015
_chemical_formula_sum            'C39 H56 Br2 Li2 N4 O2'
_chemical_formula_weight         786.57
_chemical_name_common            '5 in manuscript'
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 128.579(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.395(4)
_cell_length_b                   18.564(3)
_cell_length_c                   14.160(3)
_cell_measurement_reflns_used    715
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      13.72
_cell_measurement_theta_min      2.86
_cell_volume                     4602.1(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.448
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II Quazar'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1290
_diffrn_reflns_av_unetI/netI     0.1163
_diffrn_reflns_Laue_measured_fraction_full 0.448
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7986
_diffrn_reflns_point_group_measured_fraction_full 0.448
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         19.027
_diffrn_reflns_theta_min         1.599
_diffrn_source                   'ImuS microsource'
_exptl_absorpt_coefficient_mu    1.793
_exptl_absorpt_correction_T_max  0.9583
_exptl_absorpt_correction_T_min  0.7312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_description       needle
_exptl_crystal_F_000             1640
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         1870
_refine_ls_number_restraints     67
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0685
_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)+(0.1141P)²+15.3706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1788
_refine_ls_wR_factor_ref         0.2129
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1145
_reflns_number_total             1870
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om501229b_si_002.cif
_cod_data_source_block           mbl26
_cod_depositor_comments
'Adding full bibliography for 4085393--4085398.cif.'
_cod_original_cell_volume        4602.3(15)
_cod_database_code               4085397
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.581
_shelx_estimated_absorpt_t_max   0.948
_shelxl_version_number           2013-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Li1 Li 0.0698(13) 0.4426(12) 0.582(2) 0.055(5) Uani 1 1 d . U .
Br1 Br 0.06650(9) 0.57452(8) 0.61677(14) 0.0602(7) Uani 1 1 d . U .
C1 C 0.0966(7) 0.3852(6) 0.7436(11) 0.037(3) Uani 1 1 d . U .
N2 N 0.1521(6) 0.3362(5) 0.8198(9) 0.044(3) Uani 1 1 d . U .
C3 C 0.1547(7) 0.3212(7) 0.9187(12) 0.048(4) Uani 1 1 d . U .
H3 H 0.1893 0.2894 0.9834 0.058 Uiso 1 1 calc R U .
C4 C 0.0992(7) 0.3597(7) 0.9059(13) 0.052(4) Uani 1 1 d . U .
H4 H 0.0854 0.3600 0.9571 0.062 Uiso 1 1 calc R U .
N5 N 0.0668(6) 0.3989(5) 0.8007(10) 0.041(3) Uani 1 1 d . U .
C10 C 0.0000 0.4418(9) 0.7500 0.040(4) Uani 1 2 d S TU P
H10A H 0.0083 0.4732 0.8137 0.048 Uiso 0.5 1 calc R U P
H10B H -0.0083 0.4732 0.6863 0.048 Uiso 0.5 1 calc R U P
C11 C 0.2024(8) 0.3021(8) 0.8012(12) 0.052(3) Uani 1 1 d . U .
C12 C 0.2719(9) 0.3369(9) 0.8486(14) 0.068(4) Uani 1 1 d . U .
C13 C 0.3199(10) 0.3029(12) 0.8301(17) 0.101(6) Uani 1 1 d . U .
H13 H 0.3653 0.3258 0.8537 0.121 Uiso 1 1 calc R U .
C14 C 0.3000(13) 0.2359(13) 0.7773(19) 0.111(7) Uani 1 1 d . U .
H14 H 0.3348 0.2118 0.7709 0.134 Uiso 1 1 calc R U .
C15 C 0.2338(12) 0.2023(12) 0.7339(18) 0.116(7) Uani 1 1 d . U .
H15 H 0.2225 0.1567 0.6958 0.139 Uiso 1 1 calc R U .
C16 C 0.1811(10) 0.2349(9) 0.7450(14) 0.076(4) Uani 1 1 d . U .
C17 C 0.2957(9) 0.4087(9) 0.9204(19) 0.097(5) Uani 1 1 d . U .
H17 H 0.2599 0.4194 0.9381 0.116 Uiso 1 1 calc R U .
C19 C 0.1070(12) 0.1997(9) 0.6990(17) 0.100(5) Uani 1 1 d . U .
H19 H 0.0961 0.2126 0.7555 0.120 Uiso 1 1 calc R U .
O21 O 0.1336(7) 0.4200(6) 0.5345(11) 0.095(4) Uani 1 1 d . U .
C22 C 0.1780(12) 0.4622(11) 0.525(2) 0.145(8) Uani 1 1 d . U .
H22A H 0.2154 0.4881 0.6014 0.174 Uiso 1 1 calc R U .
H22B H 0.1463 0.4984 0.4600 0.174 Uiso 1 1 calc R U .
C23 C 0.2189(17) 0.4167(17) 0.495(3) 0.203(14) Uani 1 1 d . U .
H23A H 0.2154 0.4374 0.4271 0.244 Uiso 1 1 calc R U .
H23B H 0.2734 0.4110 0.5658 0.244 Uiso 1 1 calc R U .
C24 C 0.1795(15) 0.3497(14) 0.462(2) 0.158(9) Uani 1 1 d . U .
H24A H 0.1582 0.3369 0.3780 0.190 Uiso 1 1 calc R U .
H24B H 0.2151 0.3111 0.5164 0.190 Uiso 1 1 calc R U .
C25 C 0.1196(14) 0.3565(13) 0.470(2) 0.165(10) Uani 1 1 d . U .
H25A H 0.0696 0.3595 0.3878 0.198 Uiso 1 1 calc R U .
H25B H 0.1190 0.3144 0.5119 0.198 Uiso 1 1 calc R U .
C171 C 0.3810(17) 0.4050(15) 1.044(2) 0.258(17) Uani 1 1 d . U .
H17A H 0.3851 0.3655 1.0938 0.387 Uiso 1 1 calc R U .
H17B H 0.3938 0.4506 1.0877 0.387 Uiso 1 1 calc R U .
H17C H 0.4165 0.3965 1.0267 0.387 Uiso 1 1 calc R U .
C172 C 0.2973(19) 0.4710(12) 0.856(2) 0.221(14) Uani 1 1 d . U .
H17D H 0.2466 0.4774 0.7777 0.331 Uiso 1 1 calc R U .
H17E H 0.3347 0.4618 0.8425 0.331 Uiso 1 1 calc R U .
H17F H 0.3116 0.5147 0.9044 0.331 Uiso 1 1 calc R U .
C191 C 0.1099(12) 0.1189(10) 0.695(2) 0.154(9) Uani 1 1 d . U .
H19A H 0.0604 0.0988 0.6656 0.231 Uiso 1 1 calc R U .
H19B H 0.1499 0.1006 0.7768 0.231 Uiso 1 1 calc R U .
H19C H 0.1211 0.1046 0.6413 0.231 Uiso 1 1 calc R U .
C192 C 0.0418(10) 0.2267(10) 0.5760(17) 0.122(7) Uani 1 1 d . U .
H19D H 0.0384 0.2792 0.5784 0.184 Uiso 1 1 calc R U .
H19E H -0.0059 0.2049 0.5512 0.184 Uiso 1 1 calc R U .
H19F H 0.0502 0.2137 0.5181 0.184 Uiso 1 1 calc R U .
C31 C -0.011(4) 0.0928(15) 0.288(4) 0.29(2) Uani 1 1 d . U .
C32 C -0.0467(16) 0.1665(18) 0.215(3) 0.229(15) Uani 1 1 d . U .
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'
Br Br -0.2901 2.4595 '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
O21 Li1 C1 117.3(11) . .
O21 Li1 Br1 113.1(11) . .
C1 Li1 Br1 106.7(9) . .
O21 Li1 Br1 102.6(10) . 5_566
C1 Li1 Br1 116.0(10) . 5_566
Br1 Li1 Br1 100.1(7) . 5_566
O21 Li1 Li1 118.2(12) . 5_566
C1 Li1 Li1 124.5(12) . 5_566
Br1 Li1 Li1 50.9(6) . 5_566
Br1 Li1 Li1 49.1(6) 5_566 5_566
Li1 Br1 Li1 79.9(7) . 5_566
N5 C1 N2 101.5(10) . .
N5 C1 Li1 127.0(11) . .
N2 C1 Li1 130.9(10) . .
C1 N2 C3 111.9(10) . .
C1 N2 C11 125.1(10) . .
C3 N2 C11 123.0(10) . .
C4 C3 N2 107.6(12) . .
C4 C3 H3 126.2 . .
N2 C3 H3 126.2 . .
C3 C4 N5 104.2(12) . .
C3 C4 H4 127.9 . .
N5 C4 H4 127.9 . .
C1 N5 C4 114.7(11) . .
C1 N5 C10 123.7(10) . .
C4 N5 C10 120.9(10) . .
N5 C10 N5 112.5(14) 2_556 .
N5 C10 H10A 109.1 2_556 .
N5 C10 H10A 109.1 . .
N5 C10 H10B 109.1 2_556 .
N5 C10 H10B 109.1 . .
H10A C10 H10B 107.8 . .
C16 C11 C12 124.5(15) . .
C16 C11 N2 117.7(14) . .
C12 C11 N2 117.7(13) . .
C13 C12 C11 116.8(17) . .
C13 C12 C17 121.0(16) . .
C11 C12 C17 122.1(13) . .
C14 C13 C12 119(2) . .
C14 C13 H13 120.6 . .
C12 C13 H13 120.6 . .
C15 C14 C13 124(2) . .
C15 C14 H14 118.1 . .
C13 C14 H14 118.1 . .
C14 C15 C16 120(2) . .
C14 C15 H15 119.8 . .
C16 C15 H15 119.8 . .
C11 C16 C15 115.6(18) . .
C11 C16 C19 122.0(14) . .
C15 C16 C19 122.4(17) . .
C172 C17 C12 113.2(18) . .
C172 C17 C171 103.8(19) . .
C12 C17 C171 111.6(16) . .
C172 C17 H17 109.4 . .
C12 C17 H17 109.4 . .
C171 C17 H17 109.4 . .
C192 C19 C16 111.8(16) . .
C192 C19 C191 109.0(17) . .
C16 C19 C191 112.9(17) . .
C192 C19 H19 107.6 . .
C16 C19 H19 107.6 . .
C191 C19 H19 107.6 . .
C22 O21 C25 107.4(15) . .
C22 O21 Li1 130.9(14) . .
C25 O21 Li1 119.4(13) . .
O21 C22 C23 108.9(18) . .
O21 C22 H22A 109.9 . .
C23 C22 H22A 109.9 . .
O21 C22 H22B 109.9 . .
C23 C22 H22B 109.9 . .
H22A C22 H22B 108.3 . .
C24 C23 C22 103.1(19) . .
C24 C23 H23A 111.2 . .
C22 C23 H23A 111.2 . .
C24 C23 H23B 111.2 . .
C22 C23 H23B 111.2 . .
H23A C23 H23B 109.1 . .
C25 C24 C23 108(2) . .
C25 C24 H24A 110.0 . .
C23 C24 H24A 110.0 . .
C25 C24 H24B 110.0 . .
C23 C24 H24B 110.0 . .
H24A C24 H24B 108.4 . .
O21 C25 C24 107(2) . .
O21 C25 H25A 110.3 . .
C24 C25 H25A 110.3 . .
O21 C25 H25B 110.3 . .
C24 C25 H25B 110.3 . .
H25A C25 H25B 108.6 . .
C17 C171 H17A 109.5 . .
C17 C171 H17B 109.5 . .
H17A C171 H17B 109.5 . .
C17 C171 H17C 109.5 . .
H17A C171 H17C 109.5 . .
H17B C171 H17C 109.5 . .
C17 C172 H17D 109.5 . .
C17 C172 H17E 109.5 . .
H17D C172 H17E 109.5 . .
C17 C172 H17F 109.5 . .
H17D C172 H17F 109.5 . .
H17E C172 H17F 109.5 . .
C19 C191 H19A 109.5 . .
C19 C191 H19B 109.5 . .
H19A C191 H19B 109.5 . .
C19 C191 H19C 109.5 . .
H19A C191 H19C 109.5 . .
H19B C191 H19C 109.5 . .
C19 C192 H19D 109.5 . .
C19 C192 H19E 109.5 . .
H19D C192 H19E 109.5 . .
C19 C192 H19F 109.5 . .
H19D C192 H19F 109.5 . .
H19E C192 H19F 109.5 . .
C31 C31 C32 77(2) 2 .
C31 C31 C32 55(2) 2 2
C32 C31 C32 56(2) . 2
C31 C32 C32 71(2) . 2
C31 C32 C31 48(2) . 2
C32 C32 C31 52.8(17) 2 2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Li1 O21 1.97(2) .
Li1 C1 2.24(2) .
Li1 Br1 2.51(2) .
Li1 Br1 2.58(2) 5_566
Li1 Li1 3.26(4) 5_566
Br1 Li1 2.58(2) 5_566
C1 N5 1.354(14) .
C1 N2 1.365(14) .
N2 C3 1.394(14) .
N2 C11 1.451(15) .
C3 C4 1.343(16) .
C3 H3 0.9500 .
C4 N5 1.389(16) .
C4 H4 0.9500 .
N5 C10 1.431(13) .
C10 N5 1.431(13) 2_556
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C16 1.39(2) .
C11 C12 1.409(19) .
C12 C13 1.41(2) .
C12 C17 1.56(2) .
C13 C14 1.38(3) .
C13 H13 0.9500 .
C14 C15 1.35(3) .
C14 H14 0.9500 .
C15 C16 1.42(2) .
C15 H15 0.9500 .
C16 C19 1.50(2) .
C17 C172 1.49(2) .
C17 C171 1.60(3) .
C17 H17 1.0000 .
C19 C192 1.50(2) .
C19 C191 1.50(2) .
C19 H19 1.0000 .
O21 C22 1.342(18) .
O21 C25 1.40(2) .
C22 C23 1.49(3) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 C24 1.42(3) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 C25 1.42(2) .
C24 H24A 0.9900 .
C24 H24B 0.9900 .
C25 H25A 0.9900 .
C25 H25B 0.9900 .
C171 H17A 0.9800 .
C171 H17B 0.9800 .
C171 H17C 0.9800 .
C172 H17D 0.9800 .
C172 H17E 0.9800 .
C172 H17F 0.9800 .
C191 H19A 0.9800 .
C191 H19B 0.9800 .
C191 H19C 0.9800 .
C192 H19D 0.9800 .
C192 H19E 0.9800 .
C192 H19F 0.9800 .
C31 C31 1.44(6) 2
C31 C32 1.60(4) .
C31 C32 1.90(4) 2
C32 C32 1.66(5) 2
C32 C31 1.90(4) 2
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
N5 C1 N2 C3 0.4(12) . .
Li1 C1 N2 C3 172.0(12) . .
N5 C1 N2 C11 179.3(11) . .
Li1 C1 N2 C11 -9(2) . .
C1 N2 C3 C4 1.1(14) . .
C11 N2 C3 C4 -177.8(12) . .
N2 C3 C4 N5 -2.1(14) . .
N2 C1 N5 C4 -1.9(13) . .
Li1 C1 N5 C4 -173.9(12) . .
N2 C1 N5 C10 -172.8(11) . .
Li1 C1 N5 C10 15.2(18) . .
C3 C4 N5 C1 2.6(15) . .
C3 C4 N5 C10 173.8(11) . .
C1 N5 C10 N5 100.0(11) . 2_556
C4 N5 C10 N5 -70.4(10) . 2_556
C1 N2 C11 C16 -94.5(15) . .
C3 N2 C11 C16 84.3(16) . .
C1 N2 C11 C12 89.6(16) . .
C3 N2 C11 C12 -91.5(15) . .
C16 C11 C12 C13 4(2) . .
N2 C11 C12 C13 179.8(12) . .
C16 C11 C12 C17 -174.5(14) . .
N2 C11 C12 C17 1(2) . .
C11 C12 C13 C14 -6(2) . .
C17 C12 C13 C14 173.3(17) . .
C12 C13 C14 C15 5(3) . .
C13 C14 C15 C16 -2(3) . .
C12 C11 C16 C15 -2(2) . .
N2 C11 C16 C15 -177.3(13) . .
C12 C11 C16 C19 178.5(15) . .
N2 C11 C16 C19 3(2) . .
C14 C15 C16 C11 1(3) . .
C14 C15 C16 C19 -179.6(19) . .
C13 C12 C17 C172 69(2) . .
C11 C12 C17 C172 -112(2) . .
C13 C12 C17 C171 -48(2) . .
C11 C12 C17 C171 131.0(19) . .
C11 C16 C19 C192 83(2) . .
C15 C16 C19 C192 -97(2) . .
C11 C16 C19 C191 -153.5(16) . .
C15 C16 C19 C191 27(3) . .
C25 O21 C22 C23 -22(3) . .
Li1 O21 C22 C23 175.4(19) . .
O21 C22 C23 C24 13(3) . .
C22 C23 C24 C25 1(4) . .
C22 O21 C25 C24 23(3) . .
Li1 O21 C25 C24 -172.7(16) . .
C23 C24 C25 O21 -14(3) . .
C31 C31 C32 C32 -56(4) 2 2
C32 C31 C32 C31 56(4) 2 2
