# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1908245'
loop_
_audit_author_name
_audit_author_address
'Maciej Hodorowicz'
;Faculty of Chemistry Jagiellonian University
Poland
;
_audit_update_record             
;
2019-04-05 deposited with the CCDC.	2020-04-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H8 Cl Li3 N8 O2 W'
_chemical_formula_weight         584.42

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
W W -0.8490 6.8722 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2897(2)
_cell_length_b                   9.4735(2)
_cell_length_c                   13.3937(3)
_cell_angle_alpha                94.505(2)
_cell_angle_beta                 95.182(2)
_cell_angle_gamma                95.941(2)
_cell_volume                     1163.00(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    22288
_cell_measurement_theta_min      3.3070
_cell_measurement_theta_max      27.5990

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    5.107
_shelx_estimated_absorpt_T_min   0.428
_shelx_estimated_absorpt_T_max   0.629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.04730
_exptl_absorpt_correction_T_max  0.07245
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Spherical absorption correction
 using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      130.10(14)
_diffrn_measurement_method       'ω scans'
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.3756
_diffrn_reflns_number            51463
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.066
_diffrn_reflns_theta_max         28.706
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5760
_reflns_number_gt                5087
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0488P)²+3.8817P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5760
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0929
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
W1 W 0.12790(2) 0.29759(2) 0.26018(2) 0.02047(7) Uani 1 1 d . . . . .
N1 N 0.2212(5) 0.4475(5) 0.3915(4) 0.0345(11) Uani 1 1 d . . . . .
N16 N 0.0365(6) -0.0413(5) 0.1837(4) 0.0398(12) Uani 1 1 d . . . . .
N17 N 0.0765(6) 0.6171(5) 0.1904(4) 0.0384(11) Uani 1 1 d . . . . .
N12 N 0.0136(5) 0.2336(5) 0.3914(3) 0.0309(10) Uani 1 1 d . . . . .
C18 C -0.0991(6) 0.3063(7) 0.2165(4) 0.0343(12) Uani 1 1 d . . . . .
C4 C 0.3452(11) 0.6107(9) 0.5655(7) 0.081(4) Uani 1 1 d . . . . .
H4 H 0.388707 0.666093 0.624805 0.098 Uiso 1 1 calc R U . . .
N13 N 0.3638(5) 0.1172(5) 0.3834(4) 0.0382(11) Uani 1 1 d . . . . .
C11 C -0.0972(6) 0.1284(7) 0.3866(5) 0.0412(14) Uani 1 1 d . . . . .
H11 H -0.133130 0.081510 0.322537 0.049 Uiso 1 1 calc R U . . .
N18 N -0.2199(6) 0.3121(8) 0.1934(5) 0.0550(17) Uani 1 1 d . . . . .
C2 C 0.3227(8) 0.5572(6) 0.3869(6) 0.0479(17) Uani 1 1 d . . . . .
H2 H 0.352663 0.578695 0.323295 0.057 Uiso 1 1 calc R U . . .
C16 C 0.0676(6) 0.0777(6) 0.2095(4) 0.0269(10) Uani 1 1 d . . . . .
N14 N 0.4471(5) 0.3861(7) 0.1829(4) 0.0441(13) Uani 1 1 d . . . . .
C5 C 0.2408(11) 0.4993(9) 0.5710(6) 0.068(3) Uani 1 1 d . . . . .
H5 H 0.211070 0.477202 0.634514 0.082 Uiso 1 1 calc R U . . .
C10 C -0.1605(8) 0.0857(10) 0.4695(6) 0.061(2) Uani 1 1 d . . . . .
H10 H -0.238854 0.011623 0.462077 0.074 Uiso 1 1 calc R U . . .
C3 C 0.3855(10) 0.6408(8) 0.4735(7) 0.068(3) Uani 1 1 d . . . . .
H3 H 0.456581 0.718859 0.468261 0.082 Uiso 1 1 calc R U . . .
C17 C 0.0954(6) 0.5079(6) 0.2156(4) 0.0290(11) Uani 1 1 d . . . . .
C6 C 0.1778(8) 0.4180(7) 0.4836(4) 0.0429(16) Uani 1 1 d . . . . .
C13 C 0.2823(5) 0.1786(5) 0.3399(4) 0.0257(10) Uani 1 1 d . . . . .
C7 C 0.0622(7) 0.3001(8) 0.4832(4) 0.0416(15) Uani 1 1 d . . . . .
N15 N 0.1008(5) 0.2627(5) 0.0116(3) 0.0338(10) Uani 1 1 d . . . . .
C15 C 0.1097(5) 0.2733(5) 0.0977(4) 0.0258(10) Uani 1 1 d . . . . .
C14 C 0.3358(6) 0.3556(6) 0.2100(4) 0.0291(11) Uani 1 1 d . . . . .
C8 C 0.0022(10) 0.2597(11) 0.5702(5) 0.064(3) Uani 1 1 d . . . . .
H8 H 0.038039 0.306759 0.634233 0.077 Uiso 1 1 calc R U . . .
C9 C -0.1112(9) 0.1489(12) 0.5614(6) 0.074(3) Uani 1 1 d . . . . .
H9 H -0.152816 0.118809 0.619472 0.089 Uiso 1 1 calc R U . . .
Li1 Li -0.0590(11) 0.7604(10) 0.1404(7) 0.0315(19) Uani 1 1 d . . . . .
Cl1 Cl -0.28490(19) 0.7085(2) 0.20908(14) 0.0556(5) Uani 1 1 d . . . . .
O1 O -0.3506(7) 0.4614(9) 0.0074(5) 0.090(2) Uani 1 1 d . . . . .
O2 O -0.4197(10) 0.0694(11) 0.2065(10) 0.145(4) Uani 1 1 d . . . . .
Li3 Li -0.3467(10) 0.1949(14) -0.1142(10) 0.051(3) Uani 1 1 d . . . . .
Li2 Li -0.3554(13) 0.4613(16) 0.1485(11) 0.061(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
W1 C14 2.134(5) . ?
W1 C16 2.141(5) . ?
W1 C18 2.149(5) . ?
W1 C15 2.160(5) . ?
W1 C17 2.167(5) . ?
W1 C13 2.171(5) . ?
W1 N1 2.222(4) . ?
W1 N12 2.226(4) . ?
N1 C2 1.338(9) . ?
N1 C6 1.373(8) . ?
N16 C16 1.152(7) . ?
N16 Li1 2.010(10) 1_545 ?
N17 C17 1.139(7) . ?
N17 Li1 2.054(10) . ?
N12 C11 1.350(8) . ?
N12 C7 1.354(8) . ?
C18 N18 1.145(7) . ?
C4 C3 1.363(15) . ?
C4 C5 1.369(15) . ?
C4 H4 0.9500 . ?
N13 C13 1.147(7) . ?
C11 C10 1.372(8) . ?
C11 H11 0.9500 . ?
N18 Li2 2.076(14) . ?
C2 C3 1.397(9) . ?
C2 H2 0.9500 . ?
N14 C14 1.144(7) . ?
N14 Li2 2.005(13) 1_655 ?
C5 C6 1.395(9) . ?
C5 H5 0.9500 . ?
C10 C9 1.345(14) . ?
C10 H10 0.9500 . ?
C3 H3 0.9500 . ?
C6 C7 1.467(11) . ?
C7 C8 1.399(9) . ?
N15 C15 1.145(7) . ?
N15 Li1 2.028(10) 2_565 ?
C8 C9 1.398(14) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
Li1 Cl1 2.387(10) . ?
Cl1 Li2 2.420(16) . ?
O1 Li2 1.894(16) . ?

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
C14 W1 C16 106.8(2) . . ?
C14 W1 C18 140.3(2) . . ?
C16 W1 C18 81.2(2) . . ?
C14 W1 C15 70.8(2) . . ?
C16 W1 C15 70.89(19) . . ?
C18 W1 C15 75.8(2) . . ?
C14 W1 C17 80.7(2) . . ?
C16 W1 C17 140.25(19) . . ?
C18 W1 C17 70.5(2) . . ?
C15 W1 C17 75.40(19) . . ?
C14 W1 C13 72.76(19) . . ?
C16 W1 C13 73.50(19) . . ?
C18 W1 C13 144.1(2) . . ?
C15 W1 C13 117.52(19) . . ?
C17 W1 C13 143.05(19) . . ?
C14 W1 N1 81.7(2) . . ?
C16 W1 N1 144.31(18) . . ?
C18 W1 N1 114.8(2) . . ?
C15 W1 N1 142.03(19) . . ?
C17 W1 N1 74.70(18) . . ?
C13 W1 N1 76.40(17) . . ?
C14 W1 N12 144.37(18) . . ?
C16 W1 N12 81.80(19) . . ?
C18 W1 N12 74.50(18) . . ?
C15 W1 N12 142.13(19) . . ?
C17 W1 N12 115.12(19) . . ?
C13 W1 N12 77.06(17) . . ?
N1 W1 N12 73.10(19) . . ?
C2 N1 C6 118.8(6) . . ?
C2 N1 W1 124.2(5) . . ?
C6 N1 W1 116.8(4) . . ?
C16 N16 Li1 168.4(6) . 1_545 ?
C17 N17 Li1 151.3(6) . . ?
C11 N12 C7 117.4(5) . . ?
C11 N12 W1 124.5(4) . . ?
C7 N12 W1 118.0(4) . . ?
N18 C18 W1 179.5(7) . . ?
C3 C4 C5 118.9(7) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N12 C11 C10 123.3(7) . . ?
N12 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C18 N18 Li2 138.8(7) . . ?
N1 C2 C3 121.5(8) . . ?
N1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
N16 C16 W1 178.8(5) . . ?
C14 N14 Li2 172.6(8) . 1_655 ?
C4 C5 C6 120.2(9) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C9 C10 C11 119.8(8) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C4 C3 C2 120.1(9) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
N17 C17 W1 178.5(5) . . ?
N1 C6 C5 120.5(8) . . ?
N1 C6 C7 116.2(5) . . ?
C5 C6 C7 123.3(7) . . ?
N13 C13 W1 178.9(5) . . ?
N12 C7 C8 121.5(7) . . ?
N12 C7 C6 115.2(5) . . ?
C8 C7 C6 123.3(7) . . ?
C15 N15 Li1 173.1(6) . 2_565 ?
N15 C15 W1 178.9(5) . . ?
N14 C14 W1 179.7(6) . . ?
C9 C8 C7 118.9(7) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C10 C9 C8 119.0(6) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
N16 Li1 N15 109.3(5) 1_565 2_565 ?
N16 Li1 N17 108.7(5) 1_565 . ?
N15 Li1 N17 111.5(5) 2_565 . ?
N16 Li1 Cl1 113.0(5) 1_565 . ?
N15 Li1 Cl1 107.2(4) 2_565 . ?
N17 Li1 Cl1 107.1(4) . . ?
Li1 Cl1 Li2 102.8(4) . . ?
O1 Li2 N14 111.1(7) . 1_455 ?
O1 Li2 N18 105.8(8) . . ?
N14 Li2 N18 104.9(6) 1_455 . ?
O1 Li2 Cl1 103.3(6) . . ?
N14 Li2 Cl1 113.5(7) 1_455 . ?
N18 Li2 Cl1 118.0(6) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N12 C11 C10 -0.7(8) . . . . ?
W1 N12 C11 C10 176.2(5) . . . . ?
C6 N1 C2 C3 0.5(9) . . . . ?
W1 N1 C2 C3 -174.8(5) . . . . ?
C3 C4 C5 C6 0.3(10) . . . . ?
N12 C11 C10 C9 -0.6(10) . . . . ?
C5 C4 C3 C2 -1.1(11) . . . . ?
N1 C2 C3 C4 0.7(10) . . . . ?
C2 N1 C6 C5 -1.3(8) . . . . ?
W1 N1 C6 C5 174.3(4) . . . . ?
C2 N1 C6 C7 177.6(5) . . . . ?
W1 N1 C6 C7 -6.8(6) . . . . ?
C4 C5 C6 N1 0.9(9) . . . . ?
C4 C5 C6 C7 -177.9(6) . . . . ?
C11 N12 C7 C8 1.3(8) . . . . ?
W1 N12 C7 C8 -175.8(4) . . . . ?
C11 N12 C7 C6 -177.2(5) . . . . ?
W1 N12 C7 C6 5.6(6) . . . . ?
N1 C6 C7 N12 0.8(7) . . . . ?
C5 C6 C7 N12 179.7(5) . . . . ?
N1 C6 C7 C8 -177.7(5) . . . . ?
C5 C6 C7 C8 1.2(9) . . . . ?
N12 C7 C8 C9 -0.6(9) . . . . ?
C6 C7 C8 C9 177.8(6) . . . . ?
C11 C10 C9 C8 1.4(11) . . . . ?
C7 C8 C9 C10 -0.8(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H5 Cl1 0.95 2.92 3.685(9) 138.5 2_566 yes

_refine_diff_density_max         2.707
_refine_diff_density_min         -2.080
_refine_diff_density_rms         0.174

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1966869'
loop_
_audit_author_name
_audit_author_address
'Maciej Hodorowicz'
;Faculty of Chemistry, Jagiellonian University
Poland
;
_audit_update_record             
;
2019-11-20 deposited with the CCDC.	2020-04-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H8 Li2 N8 O W'
_chemical_formula_weight         526.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0008 0.0003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
W W -5.4734 5.5774 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2411(3)
_cell_length_b                   9.5189(3)
_cell_length_c                   13.3940(4)
_cell_angle_alpha                94.706(3)
_cell_angle_beta                 96.181(3)
_cell_angle_gamma                96.111(3)
_cell_volume                     1159.48(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5924
_cell_measurement_theta_min      4.6820
_cell_measurement_theta_max      76.2150

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    9.391
_shelx_estimated_absorpt_T_min   0.454
_shelx_estimated_absorpt_T_max   0.651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76315
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            13421
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.334
_diffrn_reflns_theta_max         76.504
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4673
_reflns_number_gt                4361
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0688P)²+3.2180P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4673
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
W1 W 0.61913(2) 0.29748(2) 0.26161(2) 0.02598(11) Uani 1 1 d . . . . .
O1 O 0.7912(4) 0.2917(4) -0.2040(3) 0.0323(8) Uani 1 1 d . . . . .
N1 N 0.5085(6) 0.2327(6) 0.3919(3) 0.0381(12) Uani 1 1 d . . . . .
N2 N 0.7171(6) 0.4452(6) 0.3942(4) 0.0426(13) Uani 1 1 d . . . . .
N6 N 0.5893(8) 0.2626(6) 0.0133(4) 0.0483(14) Uani 1 1 d . . . . .
N5 N 0.2690(7) 0.3002(9) 0.1873(6) 0.068(2) Uani 1 1 d . . . . .
N3 N 0.9351(7) 0.3928(7) 0.1830(5) 0.0572(16) Uani 1 1 d . . . . .
N4 N 0.8603(7) 0.1160(6) 0.3795(5) 0.0491(14) Uani 1 1 d . . . . .
N7 N 0.5203(6) -0.0395(5) 0.1857(4) 0.0392(11) Uani 1 1 d . . . . .
N8 N 0.5611(7) 0.6140(5) 0.1937(4) 0.0406(12) Uani 1 1 d . . . . .
C11 C 0.8255(7) 0.3599(7) 0.2109(5) 0.0385(13) Uani 1 1 d . . . . .
C14 C 0.5987(7) 0.2737(6) 0.0996(4) 0.0324(12) Uani 1 1 d . . . . .
C3 C 0.8154(8) 0.5572(7) 0.3907(6) 0.0523(19) Uani 1 1 d . . . . .
H3 H 0.841255 0.581383 0.327013 0.063 Uiso 1 1 calc R U . . .
C10 C 0.3959(8) 0.1287(7) 0.3862(5) 0.0453(16) Uani 1 1 d . . . . .
H10 H 0.357397 0.083332 0.321555 0.054 Uiso 1 1 calc R U . . .
C4 C 0.8814(11) 0.6398(10) 0.4775(6) 0.0751(18) Uani 1 1 d . . . . .
H4 H 0.951983 0.718742 0.473676 0.090 Uiso 1 1 calc R U . . .
C6 C 0.7423(11) 0.4935(10) 0.5752(7) 0.0751(18) Uani 1 1 d . . . . .
H6 H 0.715872 0.469431 0.638814 0.090 Uiso 1 1 calc R U . . .
C1 C 0.5634(9) 0.2976(8) 0.4853(4) 0.0481(18) Uani 1 1 d . . . . .
C9 C 0.3331(10) 0.0842(10) 0.4693(6) 0.064(2) Uani 1 1 d . . . . .
H9 H 0.252623 0.011737 0.460779 0.077 Uiso 1 1 calc R U . . .
C12 C 0.7789(7) 0.1770(6) 0.3372(4) 0.0354(13) Uani 1 1 d . . . . .
C2 C 0.6769(9) 0.4126(8) 0.4862(5) 0.052(2) Uani 1 1 d . . . . .
C15 C 0.5556(6) 0.0778(6) 0.2109(4) 0.0280(10) Uani 1 1 d . . . . .
C16 C 0.5826(7) 0.5060(6) 0.2188(4) 0.0326(12) Uani 1 1 d . . . . .
C7 C 0.5001(13) 0.2530(12) 0.5711(5) 0.078(4) Uani 1 1 d . . . . .
H7 H 0.536708 0.299159 0.635890 0.094 Uiso 1 1 calc R U . . .
C8 C 0.3872(12) 0.1448(11) 0.5629(7) 0.070(3) Uani 1 1 d . . . . .
H8 H 0.348271 0.113322 0.621031 0.084 Uiso 1 1 calc R U . . .
C5 C 0.8412(11) 0.6036(10) 0.5700(6) 0.0751(18) Uani 1 1 d . . . . .
H5 H 0.885058 0.658417 0.630236 0.090 Uiso 1 1 calc R U . . .
C13 C 0.3903(7) 0.2989(7) 0.2151(5) 0.0391(13) Uani 1 1 d . . . . .
Li1 Li 0.5716(19) 0.2400(16) -0.1413(11) 0.068(4) Uani 1 1 d . . . . .
Li2 Li 0.2167(18) 0.2016(15) -0.1063(16) 0.083(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
W1 C11 2.134(6) . ?
W1 C13 2.141(6) . ?
W1 C15 2.144(5) . ?
W1 C14 2.148(5) . ?
W1 C16 2.160(5) . ?
W1 C12 2.179(5) . ?
W1 N1 2.213(5) . ?
W1 N2 2.219(5) . ?
O1 Li1 2.300(18) . ?
N1 C10 1.349(9) . ?
N1 C1 1.369(8) . ?
N2 C3 1.332(10) . ?
N2 C2 1.375(10) . ?
N6 C14 1.145(8) . ?
N6 Li1 2.051(16) . ?
N5 C13 1.144(9) . ?
N3 C11 1.138(9) . ?
N4 C12 1.131(8) . ?
N7 C15 1.142(7) . ?
N7 Li1 2.019(16) 2_655 ?
N8 C16 1.138(8) . ?
N8 Li1 2.066(17) 2_665 ?
C3 C4 1.392(10) . ?
C3 H3 0.9500 . ?
C10 C9 1.384(9) . ?
C10 H10 0.9500 . ?
C4 C5 1.390(15) . ?
C4 H4 0.9500 . ?
C6 C5 1.327(16) . ?
C6 C2 1.405(10) . ?
C6 H6 0.9500 . ?
C1 C7 1.420(12) . ?
C1 C2 1.431(12) . ?
C9 C8 1.356(14) . ?
C9 H9 0.9500 . ?
C7 C8 1.374(16) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C5 H5 0.9500 . ?
Li1 Li2 3.35(2) . ?

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
C11 W1 C13 139.3(2) . . ?
C11 W1 C15 108.2(2) . . ?
C13 W1 C15 79.1(2) . . ?
C11 W1 C14 70.1(2) . . ?
C13 W1 C14 75.1(2) . . ?
C15 W1 C14 71.4(2) . . ?
C11 W1 C16 80.3(2) . . ?
C13 W1 C16 71.2(2) . . ?
C15 W1 C16 140.3(2) . . ?
C14 W1 C16 75.8(2) . . ?
C11 W1 C12 72.8(2) . . ?
C13 W1 C12 143.7(2) . . ?
C15 W1 C12 72.8(2) . . ?
C14 W1 C12 115.6(2) . . ?
C16 W1 C12 143.8(2) . . ?
C11 W1 N1 144.9(2) . . ?
C13 W1 N1 75.0(2) . . ?
C15 W1 N1 81.0(2) . . ?
C14 W1 N1 142.5(2) . . ?
C16 W1 N1 114.71(19) . . ?
C12 W1 N1 78.2(2) . . ?
C11 W1 N2 81.4(2) . . ?
C13 W1 N2 116.9(2) . . ?
C15 W1 N2 143.56(19) . . ?
C14 W1 N2 142.1(2) . . ?
C16 W1 N2 75.2(2) . . ?
C12 W1 N2 77.10(19) . . ?
N1 W1 N2 73.0(2) . . ?
C10 N1 C1 117.8(6) . . ?
C10 N1 W1 124.5(4) . . ?
C1 N1 W1 117.5(5) . . ?
C3 N2 C2 118.9(6) . . ?
C3 N2 W1 124.6(5) . . ?
C2 N2 W1 116.4(5) . . ?
C14 N6 Li1 179.3(7) . . ?
C15 N7 Li1 171.8(7) . 2_655 ?
C16 N8 Li1 153.9(7) . 2_665 ?
N3 C11 W1 179.4(7) . . ?
N6 C14 W1 179.0(6) . . ?
N2 C3 C4 122.0(9) . . ?
N2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
N1 C10 C9 123.7(8) . . ?
N1 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
C5 C4 C3 118.2(10) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C5 C6 C2 119.7(10) . . ?
C5 C6 H6 120.2 . . ?
C2 C6 H6 120.2 . . ?
N1 C1 C7 119.0(9) . . ?
N1 C1 C2 115.4(6) . . ?
C7 C1 C2 125.5(8) . . ?
C8 C9 C10 119.6(10) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
N4 C12 W1 177.7(6) . . ?
N2 C2 C6 120.3(9) . . ?
N2 C2 C1 116.7(5) . . ?
C6 C2 C1 122.9(8) . . ?
N7 C15 W1 178.5(5) . . ?
N8 C16 W1 178.0(5) . . ?
C8 C7 C1 121.6(8) . . ?
C8 C7 H7 119.2 . . ?
C1 C7 H7 119.2 . . ?
C9 C8 C7 118.1(7) . . ?
C9 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
C6 C5 C4 120.8(8) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
N5 C13 W1 177.9(6) . . ?
N7 Li1 N6 106.8(7) 2_655 . ?
N7 Li1 N8 111.1(8) 2_655 2_665 ?
N6 Li1 N8 107.7(8) . 2_665 ?
N7 Li1 O1 112.3(7) 2_655 . ?
N6 Li1 O1 113.3(8) . . ?
N8 Li1 O1 105.7(7) 2_665 . ?
N7 Li1 Li2 69.3(6) 2_655 . ?
N6 Li1 Li2 79.8(7) . . ?
N8 Li1 Li2 60.9(6) 2_665 . ?
O1 Li1 Li2 164.5(7) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N2 C3 C4 1.7(9) . . . . ?
W1 N2 C3 C4 -174.9(5) . . . . ?
C1 N1 C10 C9 0.0(9) . . . . ?
W1 N1 C10 C9 176.3(5) . . . . ?
N2 C3 C4 C5 -0.6(10) . . . . ?
C10 N1 C1 C7 0.1(8) . . . . ?
W1 N1 C1 C7 -176.6(4) . . . . ?
C10 N1 C1 C2 -176.5(5) . . . . ?
W1 N1 C1 C2 6.9(7) . . . . ?
N1 C10 C9 C8 -1.3(10) . . . . ?
C3 N2 C2 C6 -2.0(9) . . . . ?
W1 N2 C2 C6 174.9(5) . . . . ?
C3 N2 C2 C1 175.6(5) . . . . ?
W1 N2 C2 C1 -7.5(7) . . . . ?
C5 C6 C2 N2 1.3(10) . . . . ?
C5 C6 C2 C1 -176.2(6) . . . . ?
N1 C1 C2 N2 0.5(8) . . . . ?
C7 C1 C2 N2 -175.9(6) . . . . ?
N1 C1 C2 C6 178.1(6) . . . . ?
C7 C1 C2 C6 1.7(10) . . . . ?
N1 C1 C7 C8 1.2(10) . . . . ?
C2 C1 C7 C8 177.4(7) . . . . ?
C10 C9 C8 C7 2.5(10) . . . . ?
C1 C7 C8 C9 -2.5(11) . . . . ?
C2 C6 C5 C4 -0.2(11) . . . . ?
C3 C4 C5 C6 -0.2(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 N8 0.95 2.65 3.425(9) 139.4 2_666
C7 H7 N8 0.95 2.65 3.425(9) 139.4 2_666

_refine_diff_density_max         1.996
_refine_diff_density_min         -1.471
_refine_diff_density_rms         0.167



