# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_150412d
_database_code_depnum_ccdc_archive 'CCDC 1431520'
_audit_update_record             
;
2015-10-15 deposited with the CCDC.
2016-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H11 Li N14 O3'
_chemical_formula_weight         298.20

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   15.656(5)
_cell_length_b                   6.3323(19)
_cell_length_c                   23.814(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.342(3)
_cell_angle_gamma                90.00
_cell_volume                     2360.2(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2263
_cell_measurement_theta_min      2.603
_cell_measurement_theta_max      26.535

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.33
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9458
_exptl_absorpt_correction_T_max  0.9550
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5597
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2065
_reflns_number_gt                1634
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0793P)²+7.1695P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2065
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1656
_refine_ls_wR_factor_gt          0.1524
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Li1 Li 0.4843(4) 0.0250(8) 0.6092(2) 0.0353(13) Uani 1 1 d . . .
N1 N 0.44225(16) 0.4112(4) 0.67613(10) 0.0253(6) Uani 1 1 d . . .
N2 N 0.39838(18) 0.5140(4) 0.71526(11) 0.0328(7) Uani 1 1 d . . .
N3 N 0.40679(19) 0.7152(4) 0.70459(12) 0.0348(7) Uani 1 1 d . . .
N4 N 0.45506(18) 0.7461(4) 0.65941(11) 0.0303(6) Uani 1 1 d . . .
N5 N 0.56882(16) 0.6434(4) 0.56341(10) 0.0239(6) Uani 1 1 d . . .
N6 N 0.60695(17) 0.5396(4) 0.52170(11) 0.0311(7) Uani 1 1 d . . .
N7 N 0.58925(18) 0.3395(4) 0.52851(11) 0.0316(7) Uani 1 1 d . . .
N8 N 0.54054(17) 0.3104(4) 0.57368(11) 0.0282(6) Uani 1 1 d . . .
N9 N 0.66884(18) 0.2270(4) 0.69142(11) 0.0324(7) Uani 1 1 d . . .
H9 H 0.6656 0.3301 0.7148 0.039 Uiso 1 1 calc R . .
N10 N 0.6257(2) 0.0363(5) 0.70109(12) 0.0431(8) Uani 1 1 d . . .
H10A H 0.6032 0.0350 0.7355 0.052 Uiso 1 1 calc R . .
H10B H 0.6612 -0.0746 0.6979 0.052 Uiso 1 1 calc R . .
N11 N 0.75206(18) 0.4251(4) 0.63333(12) 0.0355(7) Uani 1 1 d . . .
H11 H 0.7726 0.4449 0.6006 0.043 Uiso 1 1 calc R . .
N12 N 0.7580(2) 0.5837(5) 0.67490(12) 0.0422(8) Uani 1 1 d . . .
H12A H 0.7371 0.5339 0.7067 0.063 Uiso 1 1 d R . .
H12B H 0.8125 0.6189 0.6804 0.063 Uiso 1 1 d R . .
N13 N 0.72022(17) 0.0782(4) 0.61144(11) 0.0328(7) Uani 1 1 d . . .
H13 H 0.6987 -0.0423 0.6200 0.039 Uiso 1 1 calc R . .
N14 N 0.76334(19) 0.1078(5) 0.56038(12) 0.0437(8) Uani 1 1 d . . .
H14A H 0.7984 -0.0005 0.5550 0.066 Uiso 1 1 d R . .
H14B H 0.7934 0.2270 0.5624 0.066 Uiso 1 1 d R . .
O1 O 0.44582(15) 0.2038(3) 0.67403(10) 0.0341(6) Uani 1 1 d . . .
O2 O 0.57410(15) 0.8485(3) 0.56846(10) 0.0348(6) Uani 1 1 d . . .
O3 O 0.38663(15) 0.0131(4) 0.54935(9) 0.0379(6) Uani 1 1 d . . .
H3C H 0.3900 -0.1131 0.5375 0.046 Uiso 1 1 d R . .
H3D H 0.3960 0.0948 0.5218 0.046 Uiso 1 1 d R . .
C1 C 0.47725(19) 0.5542(4) 0.64244(12) 0.0227(7) Uani 1 1 d . . .
C2 C 0.52799(18) 0.5020(4) 0.59468(12) 0.0219(6) Uani 1 1 d . . .
C3 C 0.71404(19) 0.2446(5) 0.64603(13) 0.0266(7) 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
Li1 O1 2.019(6) . ?
Li1 O2 2.056(6) 1_545 ?
Li1 O3 2.067(7) . ?
Li1 N4 2.188(6) 1_545 ?
Li1 N8 2.188(6) . ?
Li1 N10 3.077(7) . ?
N1 O1 1.315(3) . ?
N1 C1 1.336(4) . ?
N1 N2 1.339(4) . ?
N2 N3 1.306(4) . ?
N3 N4 1.343(4) . ?
N4 C1 1.329(4) . ?
N4 Li1 2.188(6) 1_565 ?
N5 O2 1.307(3) . ?
N5 C2 1.337(4) . ?
N5 N6 1.342(4) . ?
N6 N7 1.308(4) . ?
N7 N8 1.346(4) . ?
N8 C2 1.329(4) . ?
N9 C3 1.311(4) . ?
N9 N10 1.405(4) . ?
N9 H9 0.8600 . ?
N10 H10A 0.9000 . ?
N10 H10B 0.9000 . ?
N11 C3 1.326(4) . ?
N11 N12 1.412(4) . ?
N11 H11 0.8600 . ?
N12 H12A 0.8899 . ?
N12 H12B 0.8900 . ?
N13 C3 1.343(4) . ?
N13 N14 1.417(4) . ?
N13 H13 0.8600 . ?
N14 H14A 0.8899 . ?
N14 H14B 0.8899 . ?
O2 Li1 2.056(6) 1_565 ?
O3 H3C 0.8500 . ?
O3 H3D 0.8500 . ?
C1 C2 1.441(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
_geom_angle_publ_flag
O1 Li1 O2 152.3(4) . 1_545 ?
O1 Li1 O3 108.6(3) . . ?
O2 Li1 O3 99.1(3) 1_545 . ?
O1 Li1 N4 88.0(2) . 1_545 ?
O2 Li1 N4 88.5(2) 1_545 1_545 ?
O3 Li1 N4 100.7(3) . 1_545 ?
O1 Li1 N8 87.8(2) . . ?
O2 Li1 N8 88.9(2) 1_545 . ?
O3 Li1 N8 93.5(2) . . ?
N4 Li1 N8 165.7(3) 1_545 . ?
O1 Li1 N10 70.5(2) . . ?
O2 Li1 N10 81.9(2) 1_545 . ?
O3 Li1 N10 178.1(3) . . ?
N4 Li1 N10 77.7(2) 1_545 . ?
N8 Li1 N10 88.1(2) . . ?
O1 N1 C1 129.5(3) . . ?
O1 N1 N2 122.3(2) . . ?
C1 N1 N2 108.2(2) . . ?
N3 N2 N1 106.4(2) . . ?
N2 N3 N4 111.0(2) . . ?
C1 N4 N3 105.5(2) . . ?
C1 N4 Li1 120.8(3) . 1_565 ?
N3 N4 Li1 133.2(2) . 1_565 ?
O2 N5 C2 130.1(3) . . ?
O2 N5 N6 121.8(2) . . ?
C2 N5 N6 108.1(2) . . ?
N7 N6 N5 106.5(2) . . ?
N6 N7 N8 110.9(2) . . ?
C2 N8 N7 105.5(2) . . ?
C2 N8 Li1 123.0(2) . . ?
N7 N8 Li1 131.5(2) . . ?
C3 N9 N10 118.6(3) . . ?
C3 N9 H9 120.7 . . ?
N10 N9 H9 120.7 . . ?
N9 N10 Li1 104.1(2) . . ?
N9 N10 H10A 110.9 . . ?
Li1 N10 H10A 110.9 . . ?
N9 N10 H10B 110.9 . . ?
Li1 N10 H10B 110.9 . . ?
H10A N10 H10B 109.0 . . ?
C3 N11 N12 118.4(3) . . ?
C3 N11 H11 120.8 . . ?
N12 N11 H11 120.8 . . ?
N11 N12 H12A 109.0 . . ?
N11 N12 H12B 109.2 . . ?
H12A N12 H12B 109.5 . . ?
C3 N13 N14 117.7(3) . . ?
C3 N13 H13 121.1 . . ?
N14 N13 H13 121.1 . . ?
N13 N14 H14A 109.2 . . ?
N13 N14 H14B 109.2 . . ?
H14A N14 H14B 109.5 . . ?
N1 O1 Li1 127.1(2) . . ?
N5 O2 Li1 122.8(2) . 1_565 ?
Li1 O3 H3C 102.3 . . ?
Li1 O3 H3D 111.8 . . ?
H3C O3 H3D 107.6 . . ?
N4 C1 N1 108.9(3) . . ?
N4 C1 C2 127.1(3) . . ?
N1 C1 C2 124.1(3) . . ?
N8 C2 N5 109.0(3) . . ?
N8 C2 C1 126.6(3) . . ?
N5 C2 C1 124.4(3) . . ?
N9 C3 N11 121.0(3) . . ?
N9 C3 N13 119.2(3) . . ?
N11 C3 N13 119.8(3) . . ?

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
O1 N1 N2 N3 -178.8(3) . . . . ?
C1 N1 N2 N3 0.5(3) . . . . ?
N1 N2 N3 N4 0.0(4) . . . . ?
N2 N3 N4 C1 -0.5(4) . . . . ?
N2 N3 N4 Li1 170.6(3) . . . 1_565 ?
O2 N5 N6 N7 -179.8(3) . . . . ?
C2 N5 N6 N7 -0.4(3) . . . . ?
N5 N6 N7 N8 0.0(3) . . . . ?
N6 N7 N8 C2 0.4(3) . . . . ?
N6 N7 N8 Li1 178.2(3) . . . . ?
O1 Li1 N8 C2 -8.5(4) . . . . ?
O2 Li1 N8 C2 -160.9(3) 1_545 . . . ?
O3 Li1 N8 C2 100.0(3) . . . . ?
N4 Li1 N8 C2 -81.4(12) 1_545 . . . ?
N10 Li1 N8 C2 -79.0(3) . . . . ?
O1 Li1 N8 N7 174.1(3) . . . . ?
O2 Li1 N8 N7 21.6(4) 1_545 . . . ?
O3 Li1 N8 N7 -77.4(4) . . . . ?
N4 Li1 N8 N7 101.1(12) 1_545 . . . ?
N10 Li1 N8 N7 103.6(3) . . . . ?
C3 N9 N10 Li1 -68.8(3) . . . . ?
O1 Li1 N10 N9 -82.3(2) . . . . ?
O2 Li1 N10 N9 95.2(2) 1_545 . . . ?
O3 Li1 N10 N9 -141(8) . . . . ?
N4 Li1 N10 N9 -174.6(2) 1_545 . . . ?
N8 Li1 N10 N9 6.1(3) . . . . ?
C1 N1 O1 Li1 -14.5(5) . . . . ?
N2 N1 O1 Li1 164.6(3) . . . . ?
O2 Li1 O1 N1 98.8(7) 1_545 . . . ?
O3 Li1 O1 N1 -77.7(4) . . . . ?
N4 Li1 O1 N1 -178.4(3) 1_545 . . . ?
N8 Li1 O1 N1 15.3(4) . . . . ?
N10 Li1 O1 N1 104.0(3) . . . . ?
C2 N5 O2 Li1 -23.8(5) . . . 1_565 ?
N6 N5 O2 Li1 155.5(3) . . . 1_565 ?
N3 N4 C1 N1 0.8(3) . . . . ?
Li1 N4 C1 N1 -171.7(3) 1_565 . . . ?
N3 N4 C1 C2 178.8(3) . . . . ?
Li1 N4 C1 C2 6.3(5) 1_565 . . . ?
O1 N1 C1 N4 178.3(3) . . . . ?
N2 N1 C1 N4 -0.8(3) . . . . ?
O1 N1 C1 C2 0.3(5) . . . . ?
N2 N1 C1 C2 -178.8(3) . . . . ?
N7 N8 C2 N5 -0.7(3) . . . . ?
Li1 N8 C2 N5 -178.7(3) . . . . ?
N7 N8 C2 C1 177.9(3) . . . . ?
Li1 N8 C2 C1 -0.1(5) . . . . ?
O2 N5 C2 N8 -180.0(3) . . . . ?
N6 N5 C2 N8 0.7(3) . . . . ?
O2 N5 C2 C1 1.4(5) . . . . ?
N6 N5 C2 C1 -178.0(3) . . . . ?
N4 C1 C2 N8 -170.5(3) . . . . ?
N1 C1 C2 N8 7.2(5) . . . . ?
N4 C1 C2 N5 7.9(5) . . . . ?
N1 C1 C2 N5 -174.5(3) . . . . ?
N10 N9 C3 N11 176.2(3) . . . . ?
N10 N9 C3 N13 -2.4(5) . . . . ?
N12 N11 C3 N9 12.9(5) . . . . ?
N12 N11 C3 N13 -168.5(3) . . . . ?
N14 N13 C3 N9 174.7(3) . . . . ?
N14 N13 C3 N11 -3.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.070
