# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_CSMCRI-4
_database_code_depnum_ccdc_archive 'CCDC 1986383'
loop_
_audit_author_name
_audit_author_address
'Subhadip Neogi'
;CSIR CSMCRI
India
;
_audit_update_record             
;
2020-02-26 deposited with the CCDC.	2020-10-27 downloaded from the CCDC.
;
_audit_creation_date             2020-02-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C21 H12 Li N O6'
_chemical_formula_sum            'C21 H12 Li N O6'
_chemical_formula_weight         381.27
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Li -0.00003 0.00005 1.12820 0.75080 0.61750 0.46530 3.95460 1.05240 85.39050
168.26100 0.0377000011504
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   15.8425(19)
_cell_length_b                   24.624(3)
_cell_length_c                   17.549(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.466(3)
_cell_angle_gamma                90
_cell_volume                     6371.0(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    118(2)
_cell_measurement_reflns_used    2760
_cell_measurement_theta_max      25.38
_cell_measurement_theta_min      2.33
_exptl_absorpt_coefficient_mu    0.058
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6052
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.7949
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             1568.9755
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_diffrn_reflns_av_R_equivalents  0.1011
_diffrn_reflns_av_unetI/netI     0.2252
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            68049
_diffrn_reflns_theta_full        29.2883
_diffrn_reflns_theta_max         29.29
_diffrn_reflns_theta_min         2.33
_diffrn_ambient_temperature      118.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              19
_reflns_limit_h_min              -21
_reflns_limit_k_max              32
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                2088
_reflns_number_total             8158
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.0081
_refine_diff_density_min         -0.7030
_refine_diff_density_rms         0.1148
_refine_ls_d_res_high            0.7264
_refine_ls_d_res_low             8.7576
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   0.7132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     263
_refine_ls_number_reflns         8158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0960
_refine_ls_restrained_S_all      0.7132
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1653P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2521
_refine_ls_wR_factor_ref         0.3067
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00E(H00E), C00H(H00H), C00I(H00I), C00J(H00J),
 C00L(H00L), C00M(H00M), C00O(H00O), C00P(H00P), C00Q(H00Q), C00S(H00S)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O001 O 0.4194(2) 0.61831(11) 0.66294(17) 0.0962(11) Uani 1.000000 .
O002 O 0.2684(2) 0.62268(10) 0.60060(18) 0.0898(9) Uani 1.000000 .
O003 O 0.6391(2) 0.28889(13) 0.46623(19) 0.0959(10) Uani 1.000000 .
N004 N 0.3358(2) 0.36682(12) 0.6025(2) 0.0775(10) Uani 1.000000 .
O005 O 0.6558(2) 0.22686(14) 0.56119(18) 0.1017(11) Uani 1.000000 .
O006 O 0.1390(2) 0.23543(12) 0.80590(19) 0.1081(12) Uani 1.000000 .
O007 O 0.0612(2) 0.20652(15) 0.68216(18) 0.1262(15) Uani 1.000000 .
C008 C 0.3398(2) 0.53647(14) 0.6273(2) 0.0548(9) Uani 1.000000 .
C009 C 0.4179(2) 0.50734(13) 0.6498(2) 0.0545(9) Uani 1.000000 .
H009 H 0.4743(2) 0.52586(13) 0.6710(2) 0.0654(11) Uiso 1.000000 R
C00A C 0.4047(3) 0.33973(14) 0.5814(3) 0.0678(11) Uani 1.000000 .
C00B C 0.4173(2) 0.45004(12) 0.6425(2) 0.0587(10) Uani 1.000000 .
H00B H 0.4727(2) 0.43046(12) 0.6580(2) 0.0705(12) Uiso 1.000000 R
C00C C 0.3444(3) 0.59698(14) 0.6312(2) 0.0623(11) Uani 1.000000 .
C00D C 0.5439(3) 0.29337(15) 0.5438(3) 0.0645(10) Uani 1.000000 .
C00E C 0.4421(3) 0.29244(14) 0.6176(2) 0.0651(10) Uani 1.000000 .
H00E H 0.4220(3) 0.27506(14) 0.6563(2) 0.0781(13) Uiso 1.000000 R
C00F C 0.2814(3) 0.33498(14) 0.6361(3) 0.0657(10) Uani 1.000000 .
C00G C 0.3374(3) 0.42361(14) 0.6135(2) 0.0627(10) Uani 1.000000 .
C00H C 0.5038(2) 0.34097(15) 0.5057(3) 0.0674(11) Uani 1.000000 .
H00H H 0.5222(2) 0.35716(15) 0.4651(3) 0.0809(13) Uiso 1.000000 R
C00I C 0.4380(3) 0.36424(15) 0.5268(3) 0.0756(12) Uani 1.000000 .
H00I H 0.4139(3) 0.39833(15) 0.5035(3) 0.0907(15) Uiso 1.000000 R
C00J C 0.2561(3) 0.50593(16) 0.5946(3) 0.0733(11) Uani 1.000000 .
H00J H 0.1999(3) 0.52484(16) 0.5761(3) 0.0879(14) Uiso 1.000000 R
C00K C 0.6168(3) 0.2676(2) 0.5223(3) 0.0846(14) Uani 1.000000 .
C00L C 0.2560(3) 0.45173(15) 0.5898(3) 0.0692(11) Uani 1.000000 .
H00L H 0.2002(3) 0.43249(15) 0.5701(3) 0.0830(14) Uiso 1.000000 R
C00M C 0.5124(3) 0.26981(18) 0.5954(3) 0.0861(14) Uani 1.000000 .
H00M H 0.5380(3) 0.23608(18) 0.6190(3) 0.1033(16) Uiso 1.000000 R
C00N C 0.1814(3) 0.26989(16) 0.6979(3) 0.0837(13) Uani 1.000000 .
C00O C 0.2438(3) 0.30505(14) 0.7498(3) 0.0835(14) Uani 1.000000 .
H00O H 0.2520(3) 0.30771(14) 0.8061(3) 0.1002(16) Uiso 1.000000 R
C00P C 0.2172(3) 0.29814(15) 0.5834(3) 0.0809(13) Uani 1.000000 .
H00P H 0.2089(3) 0.29522(15) 0.5272(3) 0.0971(15) Uiso 1.000000 R
C00Q C 0.2936(3) 0.33614(16) 0.7163(3) 0.0817(13) Uani 1.000000 .
H00Q H 0.3388(3) 0.35959(16) 0.7514(3) 0.0980(16) Uiso 1.000000 R
C00R C 0.1182(4) 0.23520(18) 0.7287(3) 0.1078(19) Uani 1.000000 .
C00S C 0.1671(3) 0.26668(17) 0.6169(3) 0.0948(15) Uani 1.000000 .
H00S H 0.1223(3) 0.24260(17) 0.5829(3) 0.1138(18) Uiso 1.000000 R
Li4 Li -0.0654(4) 0.1948(3) 0.6489(4) 0.0702(17) Uani 1.000000 .


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
O001 C00C 1.230(5) . ?
O001 Li4 1.925(7) 5 ?
O002 C00C 1.290(4) . ?
O003 C00K 1.274(5) . ?
O003 Li4 1.971(7) 7_556 ?
N004 C00A 1.438(5) . ?
N004 C00F 1.441(4) . ?
N004 C00G 1.411(4) . ?
O005 C00K 1.243(5) . ?
O006 C00R 1.271(5) . ?
O006 Li4 1.915(7) 2_556 ?
O007 C00R 1.201(5) . ?
O007 Li4 1.896(7) . ?
C008 C009 1.358(4) . ?
C008 C00C 1.492(5) . ?
C008 C00J 1.447(5) . ?
C009 H009 0.9500 . ?
C009 C00B 1.417(4) . ?
C00A C00E 1.354(5) . ?
C00A C00I 1.391(5) . ?
C00B H00B 0.9500 . ?
C00B C00G 1.347(5) . ?
C00D C00H 1.384(5) . ?
C00D C00K 1.482(6) . ?
C00D C00M 1.318(6) . ?
C00E H00E 0.9500 . ?
C00E C00M 1.422(6) . ?
C00F C00P 1.423(5) . ?
C00F C00Q 1.350(5) . ?
C00G C00L 1.386(5) . ?
C00H H00H 0.9500 . ?
C00H C00I 1.355(5) . ?
C00I H00I 0.9500 . ?
C00J H00J 0.9500 . ?
C00J C00L 1.337(5) . ?
C00L H00L 0.9500 . ?
C00M H00M 0.9500 . ?
C00N C00O 1.378(5) . ?
C00N C00R 1.556(6) . ?
C00N C00S 1.356(5) . ?
C00O H00O 0.9500 . ?
C00O C00Q 1.377(5) . ?
C00P H00P 0.9500 . ?
C00P C00S 1.384(5) . ?
C00Q H00Q 0.9500 . ?
C00S H00S 0.9500 . ?

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
Li4 O001 C00C 120.3(3) 5 . ?
Li4 O003 C00K 130.4(4) 7_556 . ?
C00F N004 C00A 118.5(3) . . ?
C00G N004 C00A 121.2(3) . . ?
C00G N004 C00F 117.8(3) . . ?
Li4 O006 C00R 118.6(3) 2_556 . ?
Li4 O007 C00R 138.3(4) . . ?
C00C C008 C009 119.3(4) . . ?
C00J C008 C009 116.5(3) . . ?
C00J C008 C00C 124.0(3) . . ?
H009 C009 C008 119.2(2) . . ?
C00B C009 C008 121.7(3) . . ?
C00B C009 H009 119.17(19) . . ?
C00E C00A N004 121.4(4) . . ?
C00I C00A N004 119.5(3) . . ?
C00I C00A C00E 119.0(4) . . ?
H00B C00B C009 120.34(19) . . ?
C00G C00B C009 119.3(3) . . ?
C00G C00B H00B 120.3(2) . . ?
O002 C00C O001 125.3(3) . . ?
C008 C00C O001 118.0(4) . . ?
C008 C00C O002 116.6(4) . . ?
C00K C00D C00H 120.2(4) . . ?
C00M C00D C00H 118.9(4) . . ?
C00M C00D C00K 120.8(4) . . ?
H00E C00E C00A 121.3(3) . . ?
C00M C00E C00A 117.4(4) . . ?
C00M C00E H00E 121.3(3) . . ?
C00P C00F N004 118.4(4) . . ?
C00Q C00F N004 122.4(3) . . ?
C00Q C00F C00P 119.0(3) . . ?
C00B C00G N004 119.8(3) . . ?
C00L C00G N004 119.1(3) . . ?
C00L C00G C00B 121.0(3) . . ?
H00H C00H C00D 120.4(3) . . ?
C00I C00H C00D 119.3(4) . . ?
C00I C00H H00H 120.4(3) . . ?
C00H C00I C00A 122.0(4) . . ?
H00I C00I C00A 119.0(2) . . ?
H00I C00I C00H 119.0(3) . . ?
H00J C00J C008 119.2(2) . . ?
C00L C00J C008 121.6(3) . . ?
C00L C00J H00J 119.2(2) . . ?
O005 C00K O003 122.2(5) . . ?
C00D C00K O003 118.8(4) . . ?
C00D C00K O005 118.9(5) . . ?
C00J C00L C00G 120.0(4) . . ?
H00L C00L C00G 120.0(2) . . ?
H00L C00L C00J 120.0(2) . . ?
C00E C00M C00D 123.2(4) . . ?
H00M C00M C00D 118.4(3) . . ?
H00M C00M C00E 118.4(3) . . ?
C00R C00N C00O 120.8(4) . . ?
C00S C00N C00O 122.3(4) . . ?
C00S C00N C00R 116.8(4) . . ?
H00O C00O C00N 121.6(3) . . ?
C00Q C00O C00N 116.8(4) . . ?
C00Q C00O H00O 121.6(2) . . ?
H00P C00P C00F 121.1(2) . . ?
C00S C00P C00F 117.8(4) . . ?
C00S C00P H00P 121.1(3) . . ?
C00O C00Q C00F 123.3(4) . . ?
H00Q C00Q C00F 118.4(2) . . ?
H00Q C00Q C00O 118.4(2) . . ?
O007 C00R O006 124.4(4) . . ?
C00N C00R O006 114.8(4) . . ?
C00N C00R O007 120.3(4) . . ?
C00P C00S C00N 120.7(4) . . ?
H00S C00S C00N 119.7(2) . . ?
H00S C00S C00P 119.7(3) . . ?
O003 Li4 O001 106.0(3) 7_556 5_445 ?
O006 Li4 O001 109.6(4) 2_556 5_445 ?
O006 Li4 O003 95.5(3) 2_556 7_556 ?
O007 Li4 O001 106.1(3) . 5_445 ?
O007 Li4 O003 116.6(4) . 7_556 ?
O007 Li4 O006 121.9(4) . 2_556 ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.197 0.000 -0.073 1688.1 108.7 ?
2 0.155 0.500 -0.649 1688.1 108.7 ?


_olex2_submission_special_instructions 'No special instructions were received'
