#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/91/2019159.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2019159
loop_
_publ_author_name
'Tampier, Stefan'
'Burzlaff, Nicolai'
_publ_section_title
;
 Heteroscorpionate complexes based on
 bis(3,5-di-tert-butylpyrazol-1-yl)dithioacetate
;
_journal_coeditor_code           YP3040
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              981
_journal_page_last               985
_journal_paper_doi               10.1107/S0108270113021148
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          '[Li (C24 H39 N4 S2) (C4 H8 O1)], C4 H8 O'
_chemical_formula_moiety         'C28 H47 Li N4 O S2, C4 H8 O'
_chemical_formula_sum            'C32 H55 Li N4 O2 S2'
_chemical_formula_weight         598.86
_chemical_name_systematic
'[Bis(3,5-di-tert-butylpyrazol-1-yl)dithioacetato](tetrahydrofuran)lithium(I) tetrahydrofuran monosolvate'
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 105.013(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4026(3)
_cell_length_b                   16.3932(4)
_cell_length_c                   17.8867(4)
_cell_measurement_reflns_used    4077
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      23.81
_cell_measurement_theta_min      2.45
_cell_volume                     3512.56(15)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      220(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25289
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.295
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     490
_refine_ls_number_reflns         7066
_refine_ls_number_restraints     210
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.037
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0709P)²+0.7204P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1551
_reflns_number_gt                4549
_reflns_number_total             7066
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            yp3040.cif
_cod_data_source_block           compound1
_cod_original_cell_volume        3512.56(14)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2019159
_cod_database_fobs_code          2019159
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_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
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.50049(5) 0.82629(4) 0.04498(4) 0.0456(2) Uani d . 1 1 . .
S S2 0.50893(6) 0.65679(5) 0.10867(4) 0.0542(2) Uani d . 1 1 . .
N N1 0.70873(15) 0.81874(11) -0.04239(10) 0.0334(4) Uani d . 1 1 . .
N N2 0.64554(15) 0.74906(11) -0.05018(10) 0.0328(4) Uani d . 1 1 . .
N N3 0.74992(15) 0.70770(11) 0.07637(10) 0.0320(4) Uani d . 1 1 . .
N N4 0.77524(15) 0.77819(12) 0.11917(10) 0.0343(4) Uani d . 1 1 . .
C C1 0.69882(18) 0.84496(14) -0.11427(13) 0.0351(5) Uani d . 1 1 A .
C C2 0.6279(2) 0.79386(16) -0.16745(13) 0.0421(6) Uani d . 1 1 . .
H H2A 0.6076 0.7998 -0.2216 0.051 Uiso calc R 1 1 . .
C C3 0.59315(19) 0.73333(15) -0.12613(13) 0.0377(6) Uani d . 1 1 B .
C C4 0.7610(2) 0.91937(15) -0.12973(13) 0.0408(6) Uani d . 1 1 . .
C C5 0.8587(8) 0.8871(4) -0.1622(7) 0.093(3) Uani d PU 0.513(7) 1 A 1
H H5A 0.8286 0.8539 -0.2077 0.139 Uiso calc PR 0.513(7) 1 A 1
H H5B 0.909 0.8544 -0.123 0.139 Uiso calc PR 0.513(7) 1 A 1
H H5C 0.8992 0.9329 -0.176 0.139 Uiso calc PR 0.513(7) 1 A 1
C C6 0.6905(7) 0.9699(5) -0.1922(6) 0.091(3) Uani d PU 0.513(7) 1 A 1
H H6A 0.6232 0.9859 -0.1779 0.137 Uiso calc PR 0.513(7) 1 A 1
H H6B 0.6705 0.9386 -0.2398 0.137 Uiso calc PR 0.513(7) 1 A 1
H H6C 0.7316 1.0182 -0.1997 0.137 Uiso calc PR 0.513(7) 1 A 1
C C7 0.8116(12) 0.9678(6) -0.0588(5) 0.107(4) Uani d PU 0.513(7) 1 A 1
H H7A 0.7529 0.9938 -0.0406 0.161 Uiso calc PR 0.513(7) 1 A 1
H H7B 0.8605 1.0091 -0.0708 0.161 Uiso calc PR 0.513(7) 1 A 1
H H7C 0.8542 0.9319 -0.0188 0.161 Uiso calc PR 0.513(7) 1 A 1
C C5A 0.7753(10) 0.9194(6) -0.2101(5) 0.096(3) Uani d PU 0.487(7) 1 A 2
H H5AA 0.7029 0.9149 -0.2469 0.144 Uiso calc PR 0.487(7) 1 A 2
H H5AB 0.8215 0.8734 -0.2164 0.144 Uiso calc PR 0.487(7) 1 A 2
H H5AC 0.8111 0.9697 -0.2191 0.144 Uiso calc PR 0.487(7) 1 A 2
C C6A 0.6860(6) 0.9945(4) -0.1231(6) 0.081(3) Uani d PU 0.487(7) 1 A 2
H H6AA 0.6617 0.9902 -0.0758 0.121 Uiso calc PR 0.487(7) 1 A 2
H H6AB 0.6213 0.9955 -0.1673 0.121 Uiso calc PR 0.487(7) 1 A 2
H H6AC 0.7285 1.0444 -0.1219 0.121 Uiso calc PR 0.487(7) 1 A 2
C C7A 0.8691(6) 0.9301(6) -0.0697(6) 0.074(3) Uani d PU 0.487(7) 1 A 2
H H7AA 0.8563 0.9262 -0.0186 0.112 Uiso calc PR 0.487(7) 1 A 2
H H7AB 0.9002 0.9832 -0.0759 0.112 Uiso calc PR 0.487(7) 1 A 2
H H7AC 0.921 0.8879 -0.0758 0.112 Uiso calc PR 0.487(7) 1 A 2
C C8 0.5074(2) 0.66674(16) -0.15768(14) 0.0472(7) Uani d . 1 1 . .
C C9 0.4641(7) 0.6814(5) -0.2452(4) 0.088(3) Uani d PU 0.808(13) 1 B 1
H H9A 0.5252 0.6756 -0.2694 0.132 Uiso calc PR 0.808(13) 1 B 1
H H9B 0.4334 0.736 -0.2543 0.132 Uiso calc PR 0.808(13) 1 B 1
H H9C 0.4065 0.6418 -0.2671 0.132 Uiso calc PR 0.808(13) 1 B 1
C C10 0.5547(6) 0.5816(3) -0.1453(4) 0.0743(18) Uani d PU 0.808(13) 1 B 1
H H10A 0.6199 0.5779 -0.1655 0.111 Uiso calc PR 0.808(13) 1 B 1
H H10B 0.4989 0.5428 -0.172 0.111 Uiso calc PR 0.808(13) 1 B 1
H H10C 0.5758 0.5693 -0.0903 0.111 Uiso calc PR 0.808(13) 1 B 1
C C11 0.4073(5) 0.6752(4) -0.1228(4) 0.0714(17) Uani d PU 0.808(13) 1 B 1
H H11A 0.3833 0.7317 -0.1257 0.107 Uiso calc PR 0.808(13) 1 B 1
H H11B 0.4288 0.6579 -0.0691 0.107 Uiso calc PR 0.808(13) 1 B 1
H H11C 0.3465 0.6413 -0.1515 0.107 Uiso calc PR 0.808(13) 1 B 1
C C9A 0.512(4) 0.644(2) -0.2394(16) 0.095(8) Uani d PU 0.192(13) 1 B 2
H H9A1 0.4507 0.6074 -0.262 0.143 Uiso calc PR 0.192(13) 1 B 2
H H9A2 0.5822 0.6176 -0.2377 0.143 Uiso calc PR 0.192(13) 1 B 2
H H9A3 0.5049 0.6932 -0.2707 0.143 Uiso calc PR 0.192(13) 1 B 2
C C10A 0.518(2) 0.5825(13) -0.1102(17) 0.068(6) Uani d PU 0.192(13) 1 B 2
H H10D 0.4814 0.5881 -0.0686 0.102 Uiso calc PR 0.192(13) 1 B 2
H H10E 0.5961 0.5695 -0.0886 0.102 Uiso calc PR 0.192(13) 1 B 2
H H10F 0.4825 0.539 -0.1447 0.102 Uiso calc PR 0.192(13) 1 B 2
C C11A 0.397(2) 0.6983(19) -0.163(2) 0.079(7) Uani d PU 0.192(13) 1 B 2
H H11D 0.3975 0.7281 -0.1159 0.118 Uiso calc PR 0.192(13) 1 B 2
H H11E 0.3446 0.6534 -0.1689 0.118 Uiso calc PR 0.192(13) 1 B 2
H H11F 0.3751 0.7345 -0.207 0.118 Uiso calc PR 0.192(13) 1 B 2
C C12 0.64205(18) 0.70426(15) 0.01973(12) 0.0333(5) Uani d . 1 1 . .
H H12A 0.6282 0.6463 0.0046 0.04 Uiso calc R 1 1 . .
C C13 0.54890(18) 0.73052(15) 0.05815(13) 0.0366(6) Uani d . 1 1 . .
C C14 0.83005(19) 0.64977(15) 0.09937(13) 0.0359(5) Uani d . 1 1 . .
C C15 0.90923(19) 0.68445(16) 0.15871(14) 0.0412(6) Uani d . 1 1 . .
H H15A 0.9756 0.6597 0.1871 0.049 Uiso calc R 1 1 . .
C C16 0.87333(18) 0.76334(15) 0.16942(12) 0.0364(6) Uani d . 1 1 . .
C C17 0.8319(2) 0.56637(16) 0.06327(14) 0.0446(6) Uani d . 1 1 . .
C C18 0.8322(2) 0.57615(18) -0.02235(15) 0.0520(7) Uani d . 1 1 . .
H H18A 0.9002 0.6034 -0.0256 0.078 Uiso calc R 1 1 . .
H H18B 0.7682 0.6084 -0.049 0.078 Uiso calc R 1 1 . .
H H18C 0.8283 0.5228 -0.0464 0.078 Uiso calc R 1 1 . .
C C19 0.7354(3) 0.51225(17) 0.07224(17) 0.0583(8) Uani d . 1 1 . .
H H19A 0.7387 0.5063 0.1267 0.087 Uiso calc R 1 1 . .
H H19B 0.7414 0.459 0.05 0.087 Uiso calc R 1 1 . .
H H19C 0.665 0.5372 0.0457 0.087 Uiso calc R 1 1 . .
C C20 0.9405(3) 0.52413(19) 0.10463(18) 0.0653(8) Uani d . 1 1 . .
H H20A 0.9432 0.5176 0.159 0.098 Uiso calc R 1 1 . .
H H20B 1.0034 0.557 0.0997 0.098 Uiso calc R 1 1 . .
H H20C 0.9441 0.471 0.0816 0.098 Uiso calc R 1 1 . .
C C21 0.9301(2) 0.82853(17) 0.22574(14) 0.0442(6) Uani d . 1 1 . .
C C22 1.0347(2) 0.7935(2) 0.28147(17) 0.0706(9) Uani d . 1 1 . .
H H22A 1.0142 0.7477 0.3092 0.106 Uiso calc R 1 1 . .
H H22B 1.07 0.8353 0.3181 0.106 Uiso calc R 1 1 . .
H H22C 1.0864 0.7753 0.2524 0.106 Uiso calc R 1 1 . .
C C23 0.8492(2) 0.8597(2) 0.27062(17) 0.0606(8) Uani d . 1 1 . .
H H23A 0.8284 0.8152 0.2998 0.091 Uiso calc R 1 1 . .
H H23B 0.7829 0.8813 0.2347 0.091 Uiso calc R 1 1 . .
H H23C 0.8848 0.9024 0.3059 0.091 Uiso calc R 1 1 . .
C C24 0.9652(2) 0.89896(19) 0.18110(17) 0.0610(8) Uani d . 1 1 . .
H H24A 0.8995 0.923 0.1465 0.091 Uiso calc R 1 1 . .
H H24B 1.0146 0.8786 0.1512 0.091 Uiso calc R 1 1 . .
H H24C 1.0039 0.94 0.2173 0.091 Uiso calc R 1 1 . .
Li Li1 0.6941(3) 0.8768(3) 0.0583(2) 0.0407(9) Uani d . 1 1 . .
O O1 0.69211(15) 0.98799(11) 0.09766(11) 0.0536(5) Uani d D 1 1 . .
C C25 0.6046(3) 1.00941(19) 0.1326(2) 0.0699(9) Uani d D 1 1 . .
H H25A 0.5801 0.9613 0.1564 0.084 Uiso calc R 1 1 . .
H H25B 0.5405 1.0314 0.0936 0.084 Uiso calc R 1 1 . .
C C26 0.6508(4) 1.0724(3) 0.1928(3) 0.1142(16) Uani d D 1 1 . .
H H26A 0.665 1.0492 0.2449 0.137 Uiso calc R 1 1 . .
H H26B 0.5992 1.1184 0.1886 0.137 Uiso calc R 1 1 . .
C C27 0.7588(3) 1.0993(2) 0.1756(2) 0.0983(13) Uani d D 1 1 . .
H H27A 0.7624 1.1589 0.1726 0.118 Uiso calc R 1 1 . .
H H27B 0.8234 1.0799 0.2157 0.118 Uiso calc R 1 1 . .
C C28 0.7557(3) 1.06179(18) 0.0999(2) 0.0676(9) Uani d D 1 1 . .
H H28A 0.7195 1.0983 0.0574 0.081 Uiso calc R 1 1 . .
H H28B 0.8314 1.0495 0.0958 0.081 Uiso calc R 1 1 . .
O O2 0.1078(4) 0.8440(3) -0.4725(3) 0.1200(17) Uani d PDU 0.665(5) 1 C 1
C C29 0.2012(7) 0.8312(5) -0.4191(6) 0.117(2) Uani d PDU 0.665(5) 1 C 1
H H29A 0.1982 0.8578 -0.3706 0.141 Uiso calc PR 0.665(5) 1 C 1
H H29B 0.2645 0.8537 -0.4357 0.141 Uiso calc PR 0.665(5) 1 C 1
C C30 0.2151(8) 0.7404(5) -0.4072(5) 0.115(2) Uani d PDU 0.665(5) 1 C 1
H H30A 0.1874 0.7212 -0.3637 0.138 Uiso calc PR 0.665(5) 1 C 1
H H30B 0.2926 0.7229 -0.4002 0.138 Uiso calc PR 0.665(5) 1 C 1
C C31 0.1351(8) 0.7118(6) -0.4905(6) 0.127(2) Uani d PDU 0.665(5) 1 C 1
H H31A 0.1723 0.7182 -0.5322 0.152 Uiso calc PR 0.665(5) 1 C 1
H H31B 0.1101 0.6552 -0.4891 0.152 Uiso calc PR 0.665(5) 1 C 1
C C32 0.0458(7) 0.7678(5) -0.4978(5) 0.122(2) Uani d PDU 0.665(5) 1 C 1
H H32A -0.0021 0.7532 -0.4641 0.147 Uiso calc PR 0.665(5) 1 C 1
H H32B 0.0004 0.7716 -0.5514 0.147 Uiso calc PR 0.665(5) 1 C 1
O O2A 0.1108(10) 0.6896(7) -0.4520(8) 0.134(3) Uani d PDU 0.335(5) 1 C 2
C C29A 0.2054(16) 0.7054(10) -0.3954(11) 0.125(4) Uani d PDU 0.335(5) 1 C 2
H H29C 0.2716 0.6853 -0.4099 0.15 Uiso calc PR 0.335(5) 1 C 2
H H29D 0.2022 0.6801 -0.3463 0.15 Uiso calc PR 0.335(5) 1 C 2
C C30A 0.2070(15) 0.7973(10) -0.3891(9) 0.110(3) Uani d PDU 0.335(5) 1 C 2
H H30C 0.2786 0.8193 -0.3589 0.132 Uiso calc PR 0.335(5) 1 C 2
H H30D 0.1451 0.8196 -0.3709 0.132 Uiso calc PR 0.335(5) 1 C 2
C C31A 0.1889(14) 0.8052(10) -0.4830(9) 0.122(3) Uani d PDU 0.335(5) 1 C 2
H H31C 0.1663 0.8607 -0.5005 0.147 Uiso calc PR 0.335(5) 1 C 2
H H31D 0.2581 0.7919 -0.4972 0.147 Uiso calc PR 0.335(5) 1 C 2
C C32A 0.1075(17) 0.7512(12) -0.5154(9) 0.130(3) Uani d PDU 0.335(5) 1 C 2
H H32C 0.1227 0.7252 -0.5609 0.156 Uiso calc PR 0.335(5) 1 C 2
H H32D 0.0346 0.7782 -0.5308 0.156 Uiso calc PR 0.335(5) 1 C 2
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_publ_flag
C13 S1 Li1 89.79(12) ?
C1 N1 N2 105.28(17) ?
C1 N1 Li1 132.83(19) ?
N2 N1 Li1 106.99(17) ?
C3 N2 N1 111.66(17) ?
C3 N2 C12 130.00(19) ?
N1 N2 C12 118.33(17) ?
C14 N3 N4 112.00(18) ?
C14 N3 C12 130.7(2) ?
N4 N3 C12 117.12(18) ?
C16 N4 N3 104.96(19) ?
C16 N4 Li1 137.3(2) ?
N3 N4 Li1 110.76(17) ?
N1 C1 C2 110.4(2) ?
N1 C1 C4 121.0(2) ?
C2 C1 C4 128.6(2) ?
C3 C2 C1 107.3(2) ?
C3 C2 H2A 126.3 ?
C1 C2 H2A 126.3 ?
N2 C3 C2 105.3(2) ?
N2 C3 C8 127.4(2) ?
C2 C3 C8 127.2(2) ?
C6 C4 C7 112.4(6) ?
C6 C4 C5A 57.9(6) ?
C7 C4 C5A 133.7(5) ?
C6 C4 C7A 136.1(5) ?
C7 C4 C7A 39.2(5) ?
C5A C4 C7A 112.5(6) ?
C6 C4 C1 111.2(3) ?
C7 C4 C1 113.4(4) ?
C5A C4 C1 111.8(4) ?
C7A C4 C1 111.7(4) ?
C6 C4 C5 105.8(6) ?
C7 C4 C5 107.5(6) ?
C5A C4 C5 49.2(5) ?
C7A C4 C5 70.7(5) ?
C1 C4 C5 106.1(3) ?
C6 C4 C6A 51.1(5) ?
C7 C4 C6A 69.1(6) ?
C5A C4 C6A 107.1(6) ?
C7A C4 C6A 107.0(5) ?
C1 C4 C6A 106.3(3) ?
C5 C4 C6A 145.7(4) ?
C4 C5 H5A 109.5 ?
C4 C5 H5B 109.5 ?
C4 C5 H5C 109.5 ?
C4 C6 H6A 109.5 ?
C4 C6 H6B 109.5 ?
C4 C6 H6C 109.5 ?
C4 C7 H7A 109.5 ?
C4 C7 H7B 109.5 ?
C4 C7 H7C 109.5 ?
C4 C5A H5AA 109.5 ?
C4 C5A H5AB 109.5 ?
H5AA C5A H5AB 109.5 ?
C4 C5A H5AC 109.5 ?
H5AA C5A H5AC 109.5 ?
H5AB C5A H5AC 109.5 ?
C4 C6A H6AA 109.5 ?
C4 C6A H6AB 109.5 ?
H6AA C6A H6AB 109.5 ?
C4 C6A H6AC 109.5 ?
H6AA C6A H6AC 109.5 ?
H6AB C6A H6AC 109.5 ?
C4 C7A H7AA 109.5 ?
C4 C7A H7AB 109.5 ?
H7AA C7A H7AB 109.5 ?
C4 C7A H7AC 109.5 ?
H7AA C7A H7AC 109.5 ?
H7AB C7A H7AC 109.5 ?
C11A C8 C10 131.9(12) ?
C11A C8 C9A 107.1(17) ?
C10 C8 C9A 78.9(14) ?
C11A C8 C3 109.0(11) ?
C10 C8 C3 113.6(3) ?
C9A C8 C3 109.5(12) ?
C11A C8 C11 30.6(13) ?
C10 C8 C11 110.4(4) ?
C9A C8 C11 130.3(15) ?
C3 C8 C11 110.2(3) ?
C11A C8 C9 78.7(13) ?
C10 C8 C9 108.3(4) ?
C9A C8 C9 31.7(15) ?
C3 C8 C9 106.9(3) ?
C11 C8 C9 107.2(4) ?
C11A C8 C10A 106.7(14) ?
C10 C8 C10A 32.1(9) ?
C9A C8 C10A 106.3(13) ?
C3 C8 C10A 117.7(8) ?
C11 C8 C10A 80.0(10) ?
C9 C8 C10A 129.1(9) ?
C8 C9 H9A 109.5 ?
C8 C9 H9B 109.5 ?
C8 C9 H9C 109.5 ?
C8 C10 H10A 109.5 ?
C8 C10 H10B 109.5 ?
C8 C10 H10C 109.5 ?
C8 C11 H11A 109.5 ?
C8 C11 H11B 109.5 ?
C8 C11 H11C 109.5 ?
C8 C9A H9A1 109.5 ?
C8 C9A H9A2 109.5 ?
H9A1 C9A H9A2 109.5 ?
C8 C9A H9A3 109.5 ?
H9A1 C9A H9A3 109.5 ?
H9A2 C9A H9A3 109.5 ?
C8 C10A H10D 109.5 ?
C8 C10A H10E 109.5 ?
H10D C10A H10E 109.5 ?
C8 C10A H10F 109.5 ?
H10D C10A H10F 109.5 ?
H10E C10A H10F 109.5 ?
C8 C11A H11D 109.5 ?
C8 C11A H11E 109.5 ?
H11D C11A H11E 109.5 ?
C8 C11A H11F 109.5 ?
H11D C11A H11F 109.5 ?
H11E C11A H11F 109.5 ?
N3 C12 N2 110.54(17) ?
N3 C12 C13 109.69(17) ?
N2 C12 C13 115.51(19) ?
N3 C12 H12A 106.9 ?
N2 C12 H12A 106.9 ?
C13 C12 H12A 106.9 ?
C12 C13 S2 113.64(17) ?
C12 C13 S1 118.61(17) ?
S2 C13 S1 127.75(14) ?
N3 C14 C15 105.4(2) ?
N3 C14 C17 126.3(2) ?
C15 C14 C17 128.2(2) ?
C14 C15 C16 107.5(2) ?
C14 C15 H15A 126.3 ?
C16 C15 H15A 126.3 ?
N4 C16 C15 110.1(2) ?
N4 C16 C21 120.4(2) ?
C15 C16 C21 129.5(2) ?
C14 C17 C20 108.2(2) ?
C14 C17 C19 112.3(2) ?
C20 C17 C19 107.6(2) ?
C14 C17 C18 109.5(2) ?
C20 C17 C18 107.5(2) ?
C19 C17 C18 111.6(2) ?
C17 C18 H18A 109.5 ?
C17 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C17 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
C17 C19 H19A 109.5 ?
C17 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C17 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
C17 C20 H20A 109.5 ?
C17 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
C17 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
C16 C21 C23 109.3(2) ?
C16 C21 C22 109.8(2) ?
C23 C21 C22 110.2(2) ?
C16 C21 C24 109.4(2) ?
C23 C21 C24 109.7(2) ?
C22 C21 C24 108.4(2) ?
C21 C22 H22A 109.5 ?
C21 C22 H22B 109.5 ?
H22A C22 H22B 109.5 ?
C21 C22 H22C 109.5 ?
H22A C22 H22C 109.5 ?
H22B C22 H22C 109.5 ?
C21 C23 H23A 109.5 ?
C21 C23 H23B 109.5 ?
H23A C23 H23B 109.5 ?
C21 C23 H23C 109.5 ?
H23A C23 H23C 109.5 ?
H23B C23 H23C 109.5 ?
C21 C24 H24A 109.5 ?
C21 C24 H24B 109.5 ?
H24A C24 H24B 109.5 ?
C21 C24 H24C 109.5 ?
H24A C24 H24C 109.5 ?
H24B C24 H24C 109.5 ?
O1 Li1 N4 126.2(2) y
O1 Li1 N1 138.4(2) y
N4 Li1 N1 87.65(17) y
O1 Li1 S1 104.01(17) y
N4 Li1 S1 96.71(17) y
N1 Li1 S1 93.64(16) y
C25 O1 C28 104.7(2) ?
C25 O1 Li1 117.9(2) ?
C28 O1 Li1 137.3(2) ?
O1 C25 C26 106.9(3) ?
O1 C25 H25A 110.3 ?
C26 C25 H25A 110.3 ?
O1 C25 H25B 110.3 ?
C26 C25 H25B 110.3 ?
H25A C25 H25B 108.6 ?
C25 C26 C27 104.5(3) ?
C25 C26 H26A 110.9 ?
C27 C26 H26A 110.9 ?
C25 C26 H26B 110.9 ?
C27 C26 H26B 110.9 ?
H26A C26 H26B 108.9 ?
C28 C27 C26 104.5(3) ?
C28 C27 H27A 110.9 ?
C26 C27 H27A 110.9 ?
C28 C27 H27B 110.9 ?
C26 C27 H27B 110.9 ?
H27A C27 H27B 108.9 ?
O1 C28 C27 105.0(3) ?
O1 C28 H28A 110.8 ?
C27 C28 H28A 110.8 ?
O1 C28 H28B 110.8 ?
C27 C28 H28B 110.8 ?
H28A C28 H28B 108.8 ?
C29 O2 C32 112.3(5) ?
O2 C29 C30 107.9(7) ?
O2 C29 H29A 110.1 ?
C30 C29 H29A 110.1 ?
O2 C29 H29B 110.1 ?
C30 C29 H29B 110.1 ?
H29A C29 H29B 108.4 ?
C29 C30 C31 97.7(6) ?
C29 C30 H30A 112.2 ?
C31 C30 H30A 112.2 ?
C29 C30 H30B 112.2 ?
C31 C30 H30B 112.2 ?
H30A C30 H30B 109.8 ?
C32 C31 C30 100.1(7) ?
C32 C31 H31A 111.7 ?
C30 C31 H31A 111.8 ?
C32 C31 H31B 111.8 ?
C30 C31 H31B 111.8 ?
H31A C31 H31B 109.5 ?
C31 C32 O2 100.8(7) ?
C31 C32 H32A 111.6 ?
O2 C32 H32A 111.6 ?
C31 C32 H32B 111.6 ?
O2 C32 H32B 111.6 ?
H32A C32 H32B 109.4 ?
C29A O2A C32A 106.4(11) ?
O2A C29A C30A 103.7(12) ?
O2A C29A H29C 111 ?
C30A C29A H29C 111 ?
O2A C29A H29D 111 ?
C30A C29A H29D 111 ?
H29C C29A H29D 109 ?
C29A C30A C31A 90.4(11) ?
C29A C30A H30C 113.6 ?
C31A C30A H30C 113.6 ?
C29A C30A H30D 113.6 ?
C31A C30A H30D 113.6 ?
H30C C30A H30D 110.8 ?
C32A C31A C30A 106.0(11) ?
C32A C31A H31C 110.6 ?
C30A C31A H31C 110.5 ?
C32A C31A H31D 110.5 ?
C30A C31A H31D 110.5 ?
H31C C31A H31D 108.7 ?
C31A C32A O2A 104.1(11) ?
C31A C32A H32C 110.9 ?
O2A C32A H32C 110.9 ?
C31A C32A H32D 110.9 ?
O2A C32A H32D 110.9 ?
H32C C32A H32D 109 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 Li1 2.492(4) y
N1 Li1 2.085(4) y
N4 Li1 2.060(5) y
Li1 O1 1.957(5) y
S1 C13 1.675(3) y
S2 C13 1.660(2) y
N1 C1 1.331(3) ?
N1 N2 1.372(2) ?
N2 C3 1.370(3) ?
N2 C12 1.460(3) ?
N3 C14 1.359(3) ?
N3 N4 1.377(3) ?
N3 C12 1.455(3) ?
N4 C16 1.334(3) ?
C1 C2 1.396(3) ?
C1 C4 1.506(3) ?
C2 C3 1.371(3) ?
C2 H2A 0.94 ?
C3 C8 1.527(3) ?
C4 C6 1.480(7) ?
C4 C7 1.490(8) ?
C4 C5A 1.493(7) ?
C4 C7A 1.496(8) ?
C4 C5 1.566(7) ?
C4 C6A 1.567(8) ?
C5 H5A 0.97 ?
C5 H5B 0.97 ?
C5 H5C 0.97 ?
C6 H6A 0.97 ?
C6 H6B 0.97 ?
C6 H6C 0.97 ?
C7 H7A 0.97 ?
C7 H7B 0.97 ?
C7 H7C 0.97 ?
C5A H5AA 0.97 ?
C5A H5AB 0.97 ?
C5A H5AC 0.97 ?
C6A H6AA 0.97 ?
C6A H6AB 0.97 ?
C6A H6AC 0.97 ?
C7A H7AA 0.97 ?
C7A H7AB 0.97 ?
C7A H7AC 0.97 ?
C8 C11A 1.44(3) ?
C8 C10 1.509(6) ?
C8 C9A 1.52(3) ?
C8 C11 1.533(7) ?
C8 C9 1.536(6) ?
C8 C10A 1.61(2) ?
C9 H9A 0.97 ?
C9 H9B 0.97 ?
C9 H9C 0.97 ?
C10 H10A 0.97 ?
C10 H10B 0.97 ?
C10 H10C 0.97 ?
C11 H11A 0.97 ?
C11 H11B 0.97 ?
C11 H11C 0.97 ?
C9A H9A1 0.97 ?
C9A H9A2 0.97 ?
C9A H9A3 0.97 ?
C10A H10D 0.97 ?
C10A H10E 0.97 ?
C10A H10F 0.97 ?
C11A H11D 0.97 ?
C11A H11E 0.97 ?
C11A H11F 0.97 ?
C12 C13 1.550(3) ?
C12 H12A 0.99 ?
C14 C15 1.369(3) ?
C14 C17 1.515(3) ?
C15 C16 1.397(3) ?
C15 H15A 0.94 ?
C16 C21 1.512(3) ?
C17 C20 1.525(4) ?
C17 C19 1.531(4) ?
C17 C18 1.541(3) ?
C18 H18A 0.97 ?
C18 H18B 0.97 ?
C18 H18C 0.97 ?
C19 H19A 0.97 ?
C19 H19B 0.97 ?
C19 H19C 0.97 ?
C20 H20A 0.97 ?
C20 H20B 0.97 ?
C20 H20C 0.97 ?
C21 C23 1.526(4) ?
C21 C22 1.529(4) ?
C21 C24 1.530(4) ?
C22 H22A 0.97 ?
C22 H22B 0.97 ?
C22 H22C 0.97 ?
C23 H23A 0.97 ?
C23 H23B 0.97 ?
C23 H23C 0.97 ?
C24 H24A 0.97 ?
C24 H24B 0.97 ?
C24 H24C 0.97 ?
O1 C25 1.430(3) ?
O1 C28 1.439(3) ?
C25 C26 1.495(5) ?
C25 H25A 0.98 ?
C25 H25B 0.98 ?
C26 C27 1.515(5) ?
C26 H26A 0.98 ?
C26 H26B 0.98 ?
C27 C28 1.479(5) ?
C27 H27A 0.98 ?
C27 H27B 0.98 ?
C28 H28A 0.98 ?
C28 H28B 0.98 ?
O2 C29 1.314(8) ?
O2 C32 1.475(8) ?
C29 C30 1.507(8) ?
C29 H29A 0.98 ?
C29 H29B 0.98 ?
C30 C31 1.630(10) ?
C30 H30A 0.98 ?
C30 H30B 0.98 ?
C31 C32 1.418(10) ?
C31 H31A 0.98 ?
C31 H31B 0.98 ?
C32 H32A 0.98 ?
C32 H32B 0.98 ?
O2A C29A 1.361(14) ?
O2A C32A 1.511(15) ?
C29A C30A 1.511(14) ?
C29A H29C 0.98 ?
C29A H29D 0.98 ?
C30A C31A 1.641(15) ?
C30A H30C 0.98 ?
C30A H30D 0.98 ?
C31A C32A 1.354(15) ?
C31A H31C 0.98 ?
C31A H31D 0.98 ?
C32A H32C 0.98 ?
C32A H32D 0.98 ?
