# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_kr4
_database_code_depnum_ccdc_archive 'CCDC 2099918'
loop_
_audit_author_name
_audit_author_address
'Andrei V. Churakov'
;Institute of General and Inorganic Chemistry of the Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-07-28 deposited with the CCDC.	2021-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (S)-(2-(2-(methoxymethyl)pyrrolidin-1-yl)-2H-inden-2-yl)lithium 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 Li N O'
_chemical_formula_sum            'C15 H18 Li N O'
_chemical_formula_weight         235.24

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'
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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.6958(2)
_cell_length_b                   8.1833(2)
_cell_length_c                   20.4464(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1287.65(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.0

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'Siemens SMART CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8672
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_sigmaI/netI    0.0881
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2533
_reflns_number_gt                1708
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Siemens, 1995)'
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0619P)²+0.3091P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2533
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1423
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_chemical_absolute_configuration unk

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_multiplicit
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O O 0.3927(3) 0.2351(3) 0.88224(10) 0.0309(6) Uani 1 1 d . . .
N N 0.6525(3) 0.1656(3) 0.79378(11) 0.0251(6) Uani 1 1 d . . .
C1 C 0.5556(4) 0.1371(4) 0.73516(15) 0.0250(7) Uani 1 1 d . . .
C2 C 0.3753(4) 0.1025(4) 0.73331(16) 0.0264(7) Uani 1 1 d . . .
H2 H 0.3035 0.0857 0.7693 0.080 Uiso 1 1 calc R . .
C3 C 0.3245(4) 0.0981(4) 0.66682(14) 0.0241(7) Uani 1 1 d . . .
C4 C 0.1665(5) 0.0690(4) 0.63445(16) 0.0303(8) Uani 1 1 d . . .
H4 H 0.0678 0.0434 0.6586 0.080 Uiso 1 1 calc R . .
C5 C 0.1560(4) 0.0778(4) 0.56738(16) 0.0343(8) Uani 1 1 d . . .
H5 H 0.0499 0.0602 0.5467 0.080 Uiso 1 1 calc R . .
C6 C 0.3038(5) 0.1133(4) 0.52988(16) 0.0354(9) Uani 1 1 d . . .
H6 H 0.2944 0.1191 0.4846 0.080 Uiso 1 1 calc R . .
C7 C 0.4616(4) 0.1394(4) 0.55888(15) 0.0302(8) Uani 1 1 d . . .
H7 H 0.5583 0.1627 0.5332 0.080 Uiso 1 1 calc R . .
C8 C 0.4783(4) 0.1311(4) 0.62780(15) 0.0258(7) Uani 1 1 d . . .
C9 C 0.6192(4) 0.1521(4) 0.67107(15) 0.0282(7) Uani 1 1 d . . .
H9 H 0.7340 0.1722 0.6592 0.080 Uiso 1 1 calc R . .
C10 C 0.8433(4) 0.1790(4) 0.78420(16) 0.0363(9) Uani 1 1 d . . .
H10A H 0.8759 0.2896 0.7724 0.080 Uiso 1 1 calc R . .
H10B H 0.8827 0.1048 0.7503 0.080 Uiso 1 1 calc R . .
C11 C 0.9186(5) 0.1325(5) 0.84982(17) 0.0438(10) Uani 1 1 d . . .
H11A H 0.9137 0.2233 0.8803 0.080 Uiso 1 1 calc R . .
H11B H 1.0380 0.0962 0.8456 0.080 Uiso 1 1 calc R . .
C12 C 0.8010(5) -0.0057(5) 0.8713(2) 0.0518(12) Uani 1 1 d . . .
H12A H 0.8056 -0.0206 0.9184 0.080 Uiso 1 1 calc R . .
H12B H 0.8329 -0.1074 0.8501 0.080 Uiso 1 1 calc R . .
C13 C 0.6201(5) 0.0512(4) 0.84947(16) 0.0315(8) Uani 1 1 d . . .
H13 H 0.5496 -0.0419 0.8352 0.080 Uiso 1 1 calc R . .
C14 C 0.5330(5) 0.1395(5) 0.90590(16) 0.0434(9) Uani 1 1 d . . .
H14A H 0.4905 0.0605 0.9374 0.080 Uiso 1 1 calc R . .
H14B H 0.6167 0.2094 0.9277 0.080 Uiso 1 1 calc R . .
C15 C 0.2861(5) 0.2949(5) 0.93499(17) 0.0442(10) Uani 1 1 d . . .
H15A H 0.3580 0.3493 0.9666 0.080 Uiso 1 1 calc R . .
H15B H 0.2275 0.2049 0.9555 0.080 Uiso 1 1 calc R . .
H15C H 0.2019 0.3704 0.9181 0.080 Uiso 1 1 calc R . .
Li Li 0.4955(7) 0.3769(6) 0.8131(3) 0.0305(13) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O 0.0358(12) 0.0342(13) 0.0227(11) 0.0000(10) 0.0052(10) -0.0010(11)
N 0.0279(15) 0.0249(14) 0.0225(13) -0.0019(11) 0.0001(11) -0.0024(12)
C1 0.0282(18) 0.0189(16) 0.0280(17) -0.0038(15) 0.0003(14) -0.0014(14)
C2 0.0275(17) 0.0225(16) 0.0290(17) -0.0037(13) 0.0048(14) 0.0032(15)
C3 0.0309(17) 0.0198(16) 0.0215(18) -0.0021(13) -0.0030(14) -0.0005(15)
C4 0.0340(19) 0.0260(17) 0.0309(19) 0.0008(14) -0.0006(16) 0.0023(15)
C5 0.038(2) 0.030(2) 0.035(2) -0.0035(15) -0.0091(17) -0.0015(17)
C6 0.051(2) 0.0312(19) 0.0236(18) 0.0030(15) -0.0050(16) 0.0004(17)
C7 0.0400(19) 0.0261(18) 0.0244(18) 0.0027(14) 0.0048(15) 0.0008(16)
C8 0.0334(18) 0.0177(15) 0.0262(17) 0.0023(14) 0.0052(14) 0.0039(15)
C9 0.0301(18) 0.0239(16) 0.0305(17) -0.0023(14) 0.0018(15) -0.0008(15)
C10 0.0244(19) 0.045(2) 0.040(2) -0.0084(17) -0.0016(15) 0.0003(16)
C11 0.039(2) 0.044(2) 0.049(2) -0.0081(19) -0.0108(17) 0.0052(19)
C12 0.056(3) 0.038(2) 0.062(3) 0.004(2) -0.024(2) 0.0024(19)
C13 0.0395(19) 0.0223(16) 0.0326(19) 0.0042(14) -0.0076(16) 0.0007(16)
C14 0.051(2) 0.053(2) 0.0256(18) 0.0169(18) -0.0050(17) -0.002(2)
C15 0.049(2) 0.051(3) 0.032(2) -0.0103(18) 0.0146(17) -0.0127(19)
Li 0.036(3) 0.026(3) 0.030(3) 0.002(2) 0.006(2) -0.003(3)

_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
O C14 1.419(4) . ?
O C15 1.440(4) . ?
O Li 1.992(6) . ?
N C1 1.431(4) . ?
N C10 1.485(4) . ?
N C13 1.495(4) . ?
N Li 2.146(6) . ?
C1 C9 1.404(4) . ?
C1 C2 1.417(4) . ?
C1 Li 2.380(6) 3_646 ?
C1 Li 2.570(6) . ?
C2 C3 1.415(4) . ?
C2 Li 2.302(6) 3_646 ?
C3 C4 1.405(4) . ?
C3 C8 1.453(4) . ?
C3 Li 2.316(6) 3_646 ?
C4 C5 1.376(4) . ?
C5 C6 1.402(5) . ?
C6 C7 1.369(5) . ?
C7 C8 1.417(4) . ?
C8 C9 1.410(4) . ?
C8 Li 2.414(6) 3_646 ?
C9 Li 2.440(6) 3_646 ?
C10 C11 1.510(5) . ?
C11 C12 1.514(5) . ?
C12 C13 1.535(5) . ?
C13 C14 1.517(5) . ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C9 H9 0.9300 . ?
C13 H13 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?

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 O C15 111.4(3) . . ?
C14 O Li 105.1(2) . . ?
C15 O Li 124.0(3) . . ?
C1 N C10 114.6(2) . . ?
C1 N C13 116.7(2) . . ?
C10 N C13 108.1(3) . . ?
C1 N Li 89.6(2) . . ?
C10 N Li 121.4(2) . . ?
C13 N Li 105.7(2) . . ?
C9 C1 C2 109.5(3) . . ?
C9 C1 N 125.9(3) . . ?
C2 C1 N 124.4(3) . . ?
C9 C1 Li 75.4(2) . 3_646 ?
C2 C1 Li 69.4(2) . 3_646 ?
N C1 Li 125.4(2) . 3_646 ?
C9 C1 Li 125.1(2) . . ?
C2 C1 Li 89.6(2) . . ?
N C1 Li 56.60(18) . . ?
Li C1 Li 155.59(16) 3_646 . ?
C3 C2 C1 107.6(3) . . ?
C3 C2 Li 72.7(2) . 3_646 ?
C1 C2 Li 75.4(2) . 3_646 ?
C4 C3 C2 134.1(3) . . ?
C4 C3 C8 118.6(3) . . ?
C2 C3 C8 107.3(3) . . ?
C4 C3 Li 117.9(3) . 3_646 ?
C2 C3 Li 71.6(2) . 3_646 ?
C8 C3 Li 75.8(2) . 3_646 ?
C5 C4 C3 120.8(3) . . ?
C4 C5 C6 120.6(3) . . ?
C7 C6 C5 121.0(3) . . ?
C6 C7 C8 120.3(3) . . ?
C9 C8 C7 133.5(3) . . ?
C9 C8 C3 107.7(2) . . ?
C7 C8 C3 118.8(3) . . ?
C9 C8 Li 74.2(2) . 3_646 ?
C7 C8 Li 123.1(2) . 3_646 ?
C3 C8 Li 68.5(2) . 3_646 ?
C1 C9 C8 107.9(3) . . ?
C1 C9 Li 70.7(2) . 3_646 ?
C8 C9 Li 72.1(2) . 3_646 ?
N C10 C11 104.1(3) . . ?
C10 C11 C12 102.5(3) . . ?
C11 C12 C13 103.3(3) . . ?
N C13 C14 110.8(3) . . ?
N C13 C12 105.1(3) . . ?
C14 C13 C12 108.9(3) . . ?
O C14 C13 109.8(3) . . ?
O Li N 83.4(2) . . ?
O Li C2 158.6(3) . 3_656 ?
N Li C2 109.1(2) . 3_656 ?
O Li C3 124.6(3) . 3_656 ?
N Li C3 109.0(2) . 3_656 ?
C2 Li C3 35.69(13) 3_656 3_656 ?
O Li C1 138.6(3) . 3_656 ?
N Li C1 137.5(3) . 3_656 ?
C2 Li C1 35.18(13) 3_656 3_656 ?
C3 Li C1 58.20(17) 3_656 3_656 ?
O Li C8 100.4(2) . 3_656 ?
N Li C8 137.7(3) . 3_656 ?
C2 Li C8 58.61(17) 3_656 3_656 ?
C3 Li C8 35.71(13) 3_656 3_656 ?
C1 Li C8 56.66(16) 3_656 3_656 ?
O Li C9 107.4(2) . 3_656 ?
N Li C9 166.3(3) . 3_656 ?
C2 Li C9 58.04(16) 3_656 3_656 ?
C3 Li C9 58.12(16) 3_656 3_656 ?
C1 Li C9 33.84(12) 3_656 3_656 ?
C8 Li C9 33.77(12) 3_656 3_656 ?
O Li C1 93.8(2) . . ?
N Li C1 33.82(13) . . ?
C2 Li C1 106.2(2) 3_656 . ?
C3 Li C1 126.8(2) 3_656 . ?
C1 Li C1 117.1(2) 3_656 . ?
C8 Li C1 162.4(3) 3_656 . ?
C9 Li C1 148.4(2) 3_656 . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.052

_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-sensitive
