# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_li8
_database_code_depnum_ccdc_archive 'CCDC 1856206'
_audit_update_record             
;
2018-07-16 deposited with the CCDC.
2018-11-01 downloaded from the CCDC.
;
_audit_creation_date             2018-07-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H8 Cu2 N7 S2, C7 H4 N2 S'
_chemical_formula_sum            'C23 H12 Cu2 N9 S3'
_chemical_formula_weight         637.68
_chemical_melting_point          ?
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'
Cu Cu 0.3201 1.2651 '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'
S S 0.1246 0.1234 '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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   9.5199(7)
_cell_length_b                   10.2672(6)
_cell_length_c                   12.5352(8)
_cell_angle_alpha                84.614(5)
_cell_angle_beta                 70.854(6)
_cell_angle_gamma                80.244(5)
_cell_volume                     1139.75(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8532
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3000
_cell_measurement_theta_min      2.6510
_exptl_absorpt_coefficient_mu    2.177
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.858
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             638
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15203
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.72
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     49.00  75.00   0.50    7.81    --    5.00   0.00  90.00   52
  2  ω    -29.00  81.00   0.50    7.81    --   -7.70  55.00 150.00  220
  3  ω    -96.00 -65.00   0.50    7.81    --   -7.70  14.00   0.00   62
  4  ω    -23.00  72.00   0.50    7.81    --   -7.70  55.00  30.00  190
  5  ω    -91.00 -65.00   0.50    7.81    --   -7.70  55.00 -90.00   52
  6  ω      3.00  74.00   0.50    7.81    --   -7.70  55.00 -90.00  142
  7  ω    -81.00 -53.00   0.50    7.81    --   -7.70  55.00  30.00   56
  8  ω    -50.00 -24.00   0.50    7.81    --   -7.70  14.00   0.00   52
  9  ω     17.00  80.00   0.50    7.81    --   -7.70  14.00   0.00  126
 10  ω    -80.00 -54.00   0.50    7.81    --   -7.70  55.00 150.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0515785000
_diffrn_orient_matrix_UB_12      -0.0583131000
_diffrn_orient_matrix_UB_13      -0.0178598000
_diffrn_orient_matrix_UB_21      -0.0062426000
_diffrn_orient_matrix_UB_22      -0.0188737000
_diffrn_orient_matrix_UB_23      0.0570852000
_diffrn_orient_matrix_UB_31      -0.0604920000
_diffrn_orient_matrix_UB_32      -0.0341375000
_diffrn_orient_matrix_UB_33      0.0040142000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3964
_reflns_number_total             4486
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.436
_refine_diff_density_min         -2.722
_refine_diff_density_rms         0.155
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4486
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.057
_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)+(0.1041P)²+3.9915P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1563
_refine_ls_wR_factor_ref         0.1664
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 N006, C010
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N1, C00V
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00S(H00S), C00T(H00T), C00U(H00U), C00W(H00W), C00Y(H00Y), C00Z(H00Z)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cu01 Cu 0.80701(6) 0.77938(5) 0.20194(4) 0.02017(19) Uani 1 d . . . .
Cu02 Cu 0.27725(6) 0.72668(6) 0.29410(5) 0.02356(19) Uani 1 d . . . .
S003 S 0.85486(12) 1.03266(11) -0.59363(9) 0.0214(3) Uani 1 d . . . .
S004 S 0.43256(13) 0.69987(11) -0.01773(9) 0.0227(3) Uani 1 d . . . .
S005 S -0.2071(3) 0.5008(2) 1.11265(16) 0.0637(5) Uani 1 d . . . .
N006 N -0.1302(6) 0.5593(10) 0.8963(9) 0.0119(11) Uani 1 d . . . U
N007 N 0.8577(4) 0.9695(4) -0.3702(3) 0.0206(8) Uani 1 d . . . .
N008 N 0.8580(4) 0.8519(4) 0.0321(3) 0.0200(8) Uani 1 d . . . .
N009 N 0.4233(4) 0.4949(4) 0.1506(3) 0.0211(8) Uani 1 d . . . .
N00A N 0.2115(4) 0.6565(4) 0.4665(3) 0.0216(8) Uani 1 d . . . .
N00B N 0.4079(5) 0.1387(4) 0.4613(3) 0.0274(9) Uani 1 d . . . .
N00C N 0.5982(5) 0.7737(5) 0.2461(4) 0.0307(9) Uani 1 d . . . .
N00D N 1.1011(5) 0.7377(4) 0.2528(3) 0.0272(9) Uani 1 d . . . .
C00E C 0.9875(5) 0.7491(4) 0.2367(4) 0.0174(8) Uani 1 d . . . .
C00F C 0.4746(5) 0.7616(4) 0.2610(4) 0.0201(9) Uani 1 d . . . .
C00G C 0.4508(5) 0.2852(5) 0.2561(4) 0.0195(9) Uani 1 d . . . .
C00H C 0.9620(5) 0.9493(4) -0.3212(4) 0.0197(9) Uani 1 d . . . .
C00I C 0.1221(5) 0.5859(4) 0.6972(4) 0.0202(9) Uani 1 d . . . .
C00J C 0.9232(5) 0.9977(4) -0.4809(4) 0.0197(9) Uani 1 d . . . .
C00K C 0.9287(5) 0.9172(4) -0.1993(4) 0.0179(9) Uani 1 d . . . .
C00L C 0.7499(5) 0.8918(5) -0.0165(4) 0.0253(10) Uani 1 d . . . .
H00L H 0.6501 0.8968 0.0290 0.030 Uiso 1 calc . . R .
C00M C 1.0018(5) 0.8472(4) -0.0353(4) 0.0201(9) Uani 1 d . . . .
H00M H 1.0778 0.8220 -0.0030 0.024 Uiso 1 calc . . R .
C00N C 0.4900(6) 0.0851(5) 0.3626(4) 0.0261(10) Uani 1 d . . . .
H00N H 0.5335 -0.0031 0.3636 0.031 Uiso 1 calc . . R .
C00O C 0.5136(5) 0.1533(5) 0.2595(4) 0.0235(9) Uani 1 d . . . .
H00O H 0.5709 0.1115 0.1931 0.028 Uiso 1 calc . . R .
C00P C 1.0415(5) 0.8780(4) -0.1493(4) 0.0209(9) Uani 1 d . . . .
H00P H 1.1423 0.8728 -0.1928 0.025 Uiso 1 calc . . R .
C00Q C 0.3122(5) 0.6265(5) 0.5231(4) 0.0238(9) Uani 1 d . . . .
H00Q H 0.4130 0.6305 0.4837 0.029 Uiso 1 calc . . R .
C00R C 0.4716(5) 0.3676(5) 0.1507(4) 0.0208(9) Uani 1 d . . . .
C00S C 0.3653(5) 0.3420(5) 0.3587(4) 0.0242(10) Uani 1 d . . . .
H00S H 0.3210 0.4301 0.3606 0.029 Uiso 1 calc . . R .
C00T C 0.2726(5) 0.5901(5) 0.6371(4) 0.0248(10) Uani 1 d . . . .
H00T H 0.3456 0.5689 0.6728 0.030 Uiso 1 calc . . R .
C00U C 0.0668(5) 0.6511(5) 0.5255(4) 0.0241(10) Uani 1 d . . . .
H00U H -0.0039 0.6712 0.4876 0.029 Uiso 1 calc . . R .
C00V C 0.0725(5) 0.5521(4) 0.8183(4) 0.0200(9) Uani 1 d . . . U
C00W C 0.7793(5) 0.9254(5) -0.1294(4) 0.0255(10) Uani 1 d . . . .
H00W H 0.7010 0.9532 -0.1590 0.031 Uiso 1 calc . . R .
C00X C 0.4623(5) 0.5431(4) 0.0420(4) 0.0201(9) Uani 1 d . . . .
C00Y C 0.3477(5) 0.2650(5) 0.4569(4) 0.0256(10) Uani 1 d . . . .
H00Y H 0.2900 0.3039 0.5246 0.031 Uiso 1 calc . . R .
C00Z C 0.0173(5) 0.6175(5) 0.6391(4) 0.0254(10) Uani 1 d . . . .
H00Z H -0.0844 0.6158 0.6767 0.030 Uiso 1 calc . . R .
C010 C -0.0719(6) 0.5131(5) 0.9995(4) 0.0264(10) Uani 1 d . . . U
N1 N -0.0831(11) 0.5583(12) 0.8838(9) 0.049(3) Uani 1 d . . . U


_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
Cu01 N008 2.114(4) . ?
Cu01 N00C 1.890(5) . ?
Cu01 C00E 1.877(4) . ?
Cu02 N00A 2.134(4) . ?
Cu02 N00D 1.894(4) 1_455 ?
Cu02 C00F 1.876(4) . ?
S003 C00H 1.751(5) 2_774 ?
S003 C00J 1.725(5) . ?
S004 C00R 1.759(5) 2_665 ?
S004 C00X 1.730(5) . ?
S005 C00V 1.757(5) 2_567 ?
S005 C010 1.584(6) . ?
N006 C00V 1.848(7) . ?
N006 C010 1.573(12) . ?
N007 C00H 1.308(6) . ?
N007 C00J 1.348(6) . ?
N008 C00L 1.348(6) . ?
N008 C00M 1.348(6) . ?
N009 C00R 1.310(6) . ?
N009 C00X 1.356(6) . ?
N00A C00Q 1.350(6) . ?
N00A C00U 1.341(6) . ?
N00B C00N 1.339(7) . ?
N00B C00Y 1.330(7) . ?
N00C C00F 1.156(7) . ?
N00D Cu02 1.894(4) 1_655 ?
N00D C00E 1.149(7) . ?
C00G C00O 1.387(6) . ?
C00G C00R 1.476(6) . ?
C00G C00S 1.396(6) . ?
C00H S003 1.751(5) 2_774 ?
C00H C00K 1.471(6) . ?
C00I C00T 1.389(7) . ?
C00I C00V 1.461(6) . ?
C00I C00Z 1.398(7) . ?
C00J C00J 1.390(9) 2_774 ?
C00K C00P 1.399(6) . ?
C00K C00W 1.398(6) . ?
C00L H00L 0.9300 . ?
C00L C00W 1.372(7) . ?
C00M H00M 0.9300 . ?
C00M C00P 1.374(6) . ?
C00N H00N 0.9300 . ?
C00N C00O 1.381(7) . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00Q C00T 1.385(7) . ?
C00R S004 1.759(5) 2_665 ?
C00S H00S 0.9300 . ?
C00S C00Y 1.377(7) . ?
C00T H00T 0.9300 . ?
C00U H00U 0.9300 . ?
C00U C00Z 1.376(7) . ?
C00V S005 1.757(5) 2_567 ?
C00V N1 1.433(11) . ?
C00W H00W 0.9300 . ?
C00X C00X 1.368(9) 2_665 ?
C00Y H00Y 0.9300 . ?
C00Z H00Z 0.9300 . ?
C010 C010 1.354(9) 2_567 ?
C010 N1 1.513(12) . ?

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
N00C Cu01 N008 103.23(16) . . ?
C00E Cu01 N008 107.17(16) . . ?
C00E Cu01 N00C 149.59(18) . . ?
N00D Cu02 N00A 104.08(16) 1_455 . ?
C00F Cu02 N00A 105.67(17) . . ?
C00F Cu02 N00D 149.87(18) . 1_455 ?
C00J S003 C00H 87.8(2) . 2_774 ?
C00X S004 C00R 87.8(2) . 2_665 ?
C010 S005 C00V 87.7(3) . 2_567 ?
C010 N006 C00V 83.0(4) . . ?
C00H N007 C00J 108.2(4) . . ?
C00L N008 Cu01 121.8(3) . . ?
C00M N008 Cu01 120.7(3) . . ?
C00M N008 C00L 117.1(4) . . ?
C00R N009 C00X 108.3(4) . . ?
C00Q N00A Cu02 121.2(3) . . ?
C00U N00A Cu02 121.2(3) . . ?
C00U N00A C00Q 117.3(4) . . ?
C00Y N00B C00N 116.6(4) . . ?
C00F N00C Cu01 171.4(4) . . ?
C00E N00D Cu02 174.0(4) . 1_655 ?
N00D C00E Cu01 175.3(4) . . ?
N00C C00F Cu02 174.2(4) . . ?
C00O C00G C00R 123.4(4) . . ?
C00O C00G C00S 117.6(4) . . ?
C00S C00G C00R 119.0(4) . . ?
N007 C00H S003 117.0(3) . 2_774 ?
N007 C00H C00K 122.4(4) . . ?
C00K C00H S003 120.5(3) . 2_774 ?
C00T C00I C00V 121.5(4) . . ?
C00T C00I C00Z 118.2(4) . . ?
C00Z C00I C00V 120.3(4) . . ?
N007 C00J S003 133.1(4) . . ?
N007 C00J C00J 118.1(5) . 2_774 ?
C00J C00J S003 108.8(4) 2_774 . ?
C00P C00K C00H 122.5(4) . . ?
C00W C00K C00H 119.7(4) . . ?
C00W C00K C00P 117.8(4) . . ?
N008 C00L H00L 118.2 . . ?
N008 C00L C00W 123.5(4) . . ?
C00W C00L H00L 118.2 . . ?
N008 C00M H00M 118.4 . . ?
N008 C00M C00P 123.3(4) . . ?
C00P C00M H00M 118.4 . . ?
N00B C00N H00N 118.2 . . ?
N00B C00N C00O 123.7(5) . . ?
C00O C00N H00N 118.2 . . ?
C00G C00O H00O 120.4 . . ?
C00N C00O C00G 119.1(4) . . ?
C00N C00O H00O 120.4 . . ?
C00K C00P H00P 120.4 . . ?
C00M C00P C00K 119.2(4) . . ?
C00M C00P H00P 120.4 . . ?
N00A C00Q H00Q 118.4 . . ?
N00A C00Q C00T 123.2(4) . . ?
C00T C00Q H00Q 118.4 . . ?
N009 C00R S004 116.3(3) . 2_665 ?
N009 C00R C00G 122.2(4) . . ?
C00G C00R S004 121.4(3) . 2_665 ?
C00G C00S H00S 120.6 . . ?
C00Y C00S C00G 118.7(4) . . ?
C00Y C00S H00S 120.6 . . ?
C00I C00T H00T 120.6 . . ?
C00Q C00T C00I 118.9(4) . . ?
C00Q C00T H00T 120.6 . . ?
N00A C00U H00U 118.3 . . ?
N00A C00U C00Z 123.4(4) . . ?
C00Z C00U H00U 118.3 . . ?
S005 C00V N006 120.6(4) 2_567 . ?
C00I C00V S005 119.5(3) . 2_567 ?
C00I C00V N006 119.8(5) . . ?
N1 C00V S005 118.1(5) . 2_567 ?
N1 C00V N006 2.8(8) . . ?
N1 C00V C00I 122.4(6) . . ?
C00K C00W H00W 120.5 . . ?
C00L C00W C00K 119.1(4) . . ?
C00L C00W H00W 120.5 . . ?
N009 C00X S004 132.4(3) . . ?
N009 C00X C00X 118.4(5) . 2_665 ?
C00X C00X S004 109.1(4) 2_665 . ?
N00B C00Y C00S 124.3(5) . . ?
N00B C00Y H00Y 117.9 . . ?
C00S C00Y H00Y 117.9 . . ?
C00I C00Z H00Z 120.5 . . ?
C00U C00Z C00I 119.1(4) . . ?
C00U C00Z H00Z 120.5 . . ?
N006 C010 S005 111.3(4) . . ?
C010 C010 S005 120.4(6) 2_567 . ?
C010 C010 N006 128.3(6) 2_567 . ?
C010 C010 N1 112.7(7) 2_567 . ?
N1 C010 S005 126.8(5) . . ?
N1 C010 N006 15.6(5) . . ?
C00V N1 C010 101.1(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.450
_oxdiff_exptl_absorpt_empirical_full_min 0.835
