# 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_10rt
_database_code_depnum_ccdc_archive 'CCDC 1845829'
_audit_update_record             
;
2018-07-26 deposited with the CCDC.
2018-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H16 Li N O5'
_chemical_formula_weight         273.21

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   5.4363(7)
_cell_length_b                   10.3418(13)
_cell_length_c                   11.8349(17)
_cell_angle_alpha                90
_cell_angle_beta                 99.739(5)
_cell_angle_gamma                90
_cell_volume                     655.78(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    500
_cell_measurement_theta_min      2
_cell_measurement_theta_max      20

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6323
_exptl_absorpt_correction_T_max  0.7450
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2435
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.493
_diffrn_reflns_theta_max         23.854
_diffrn_reflns_theta_full        23.854
_diffrn_measured_fraction_theta_max 0.780
_diffrn_measured_fraction_theta_full 0.780
_diffrn_reflns_Laue_measured_fraction_max 0.780
_diffrn_reflns_Laue_measured_fraction_full 0.780
_diffrn_reflns_point_group_measured_fraction_max 0.723
_diffrn_reflns_point_group_measured_fraction_full 0.724
_reflns_number_total             1462
_reflns_number_gt                1225
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_max     0.659
_reflns_Friedel_fraction_full    0.659

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0432P)²] 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_abs_structure_details 
;
 Flack x determined using 469 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.9(10)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         1462
_refine_ls_number_parameters     182
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.0875
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.033
_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_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
O1 O 1.3471(6) 0.2934(4) 0.7292(3) 0.0380(10) Uani 1 1 d . . . . .
Li1 Li 1.0260(15) 0.2788(9) 0.6463(7) 0.037(2) Uani 1 1 d . . . . .
C2 C 1.5655(10) 0.2566(4) 0.7591(4) 0.0235(13) Uani 1 1 d . . . . .
O3 O 1.7475(7) 0.3014(4) 0.7183(3) 0.0430(10) Uani 1 1 d . . . . .
C4 C 1.6246(9) 0.1588(5) 0.8538(4) 0.0251(13) Uani 1 1 d . . . . .
C5 C 1.4711(11) 0.0522(6) 0.8620(5) 0.0410(15) Uani 1 1 d . . . . .
C6 C 1.5244(14) -0.0328(7) 0.9525(6) 0.061(2) Uani 1 1 d . . . . .
H6 H 1.4215 -0.1038 0.9570 0.073 Uiso 1 1 calc R U . . .
C7 C 1.7250(15) -0.0135(8) 1.0346(6) 0.067(2) Uani 1 1 d . . . . .
H7 H 1.7563 -0.0700 1.0965 0.080 Uiso 1 1 calc R U . . .
C8 C 1.8834(14) 0.0881(7) 1.0283(5) 0.067(2) Uani 1 1 d . . . . .
H8 H 2.0232 0.0994 1.0847 0.080 Uiso 1 1 calc R U . . .
C9 C 1.8338(11) 0.1755(6) 0.9361(5) 0.0458(16) Uani 1 1 d . . . . .
H9 H 1.9417 0.2442 0.9307 0.055 Uiso 1 1 calc R U . . .
O10 O 1.2773(9) 0.0362(4) 0.7735(4) 0.0718(15) Uani 1 1 d . . . . .
C11 C 1.1061(12) -0.0665(6) 0.7760(6) 0.071(2) Uani 1 1 d . . . . .
H11A H 1.1929 -0.1475 0.7783 0.107 Uiso 1 1 calc R U . . .
H11B H 0.9803 -0.0630 0.7085 0.107 Uiso 1 1 calc R U . . .
H11C H 1.0289 -0.0585 0.8429 0.107 Uiso 1 1 calc R U . . .
O12 O 0.9720(6) 0.1380(3) 0.5342(3) 0.0377(11) Uani 1 1 d . . . . .
C13 C 1.0979(9) 0.0608(5) 0.4864(4) 0.0244(13) Uani 1 1 d . . . . .
O14 O 1.0181(6) -0.0445(3) 0.4425(3) 0.0359(11) Uani 1 1 d . . . . .
C15 C 1.3664(9) 0.1023(4) 0.4799(4) 0.0241(13) Uani 1 1 d . . . . .
H15 H 1.4686 0.0974 0.5564 0.029 Uiso 1 1 calc R U . . .
N16 N 1.4793(7) 0.0179(4) 0.3980(3) 0.0249(10) Uani 1 1 d . . . . .
H16A H 1.6319 -0.0068 0.4303 0.030 Uiso 1 1 calc R U . . .
H16B H 1.3864 -0.0525 0.3810 0.030 Uiso 1 1 calc R U . . .
C17 C 1.4915(10) 0.0935(5) 0.2915(4) 0.0387(16) Uani 1 1 d . . . . .
H17A H 1.4191 0.0450 0.2238 0.046 Uiso 1 1 calc R U . . .
H17B H 1.6627 0.1152 0.2860 0.046 Uiso 1 1 calc R U . . .
C18 C 1.3425(11) 0.2127(5) 0.3040(5) 0.0466(17) Uani 1 1 d . . . . .
H18A H 1.1670 0.1987 0.2744 0.056 Uiso 1 1 calc R U . . .
H18B H 1.4016 0.2850 0.2639 0.056 Uiso 1 1 calc R U . . .
C19 C 1.3838(10) 0.2368(5) 0.4317(4) 0.0344(14) Uani 1 1 d . . . . .
H19A H 1.2560 0.2931 0.4526 0.041 Uiso 1 1 calc R U . . .
H19B H 1.5465 0.2748 0.4581 0.041 Uiso 1 1 calc R 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
O1 C2 1.240(6) . ?
O1 Li1 1.858(9) . ?
Li1 O3 1.873(9) 1_455 ?
Li1 O12 1.958(9) . ?
Li1 O14 2.102(10) 2_756 ?
C2 O3 1.260(6) . ?
C2 C4 1.503(7) . ?
O3 Li1 1.873(9) 1_655 ?
C4 C9 1.377(7) . ?
C4 C5 1.396(7) . ?
C5 O10 1.364(7) . ?
C5 C6 1.378(8) . ?
C6 C7 1.347(9) . ?
C7 C8 1.368(9) . ?
C8 C9 1.408(8) . ?
O10 C11 1.415(7) . ?
O12 C13 1.248(6) . ?
C13 O14 1.252(6) . ?
C13 C15 1.536(7) . ?
O14 Li1 2.102(10) 2_746 ?
C15 N16 1.509(6) . ?
C15 C19 1.512(6) . ?
N16 C17 1.495(6) . ?
C17 C18 1.496(7) . ?
C18 C19 1.510(7) . ?

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
C2 O1 Li1 153.4(4) . . ?
O1 Li1 O3 120.6(5) . 1_455 ?
O1 Li1 O12 116.0(5) . . ?
O3 Li1 O12 111.2(4) 1_455 . ?
O1 Li1 O14 102.2(4) . 2_756 ?
O3 Li1 O14 94.9(4) 1_455 2_756 ?
O12 Li1 O14 108.4(4) . 2_756 ?
O1 C2 O3 123.6(5) . . ?
O1 C2 C4 119.5(5) . . ?
O3 C2 C4 116.8(5) . . ?
C2 O3 Li1 151.1(5) . 1_655 ?
C9 C4 C5 118.8(5) . . ?
C9 C4 C2 119.3(5) . . ?
C5 C4 C2 121.9(5) . . ?
O10 C5 C6 123.5(6) . . ?
O10 C5 C4 115.8(5) . . ?
C6 C5 C4 120.6(6) . . ?
C7 C6 C5 120.2(7) . . ?
C6 C7 C8 121.0(7) . . ?
C7 C8 C9 119.7(7) . . ?
C4 C9 C8 119.6(6) . . ?
C5 O10 C11 120.0(5) . . ?
C13 O12 Li1 138.8(4) . . ?
O12 C13 O14 124.5(5) . . ?
O12 C13 C15 116.3(5) . . ?
O14 C13 C15 119.2(5) . . ?
C13 O14 Li1 165.0(4) . 2_746 ?
N16 C15 C19 103.4(4) . . ?
N16 C15 C13 111.4(4) . . ?
C19 C15 C13 113.4(4) . . ?
C17 N16 C15 108.7(4) . . ?
N16 C17 C18 104.2(4) . . ?
C17 C18 C19 104.1(5) . . ?
C18 C19 C15 102.5(4) . . ?

_refine_diff_density_max         0.136
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.041


# start Validation Reply Form
_vrf_THETM01_E_1_0rt             
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: poor diffracting crystal
;
_vrf_PLAT029_E_1_0rt             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.780 Why?  
RESPONSE: poor diffracting crystal
;
_vrf_PLAT089_E_1_0rt             
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       4.61 Note  
RESPONSE: poor diffracting crystal
;
_vrf_PLAT911_E_1_0rt             
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.569        200 Report
RESPONSE: poor diffracting crystal
;
# end Validation Reply Form
####################################################################### 
# 
# 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_1_007
_database_code_depnum_ccdc_archive 'CCDC 1845831'
_audit_update_record             
;
2018-05-28 deposited with the CCDC.
2018-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6.47 H7.93 Li0.50 N0.50 O2.47'
_chemical_formula_weight         135.63

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   5.4205(7)
_cell_length_b                   10.3464(13)
_cell_length_c                   11.5006(15)
_cell_angle_alpha                90
_cell_angle_beta                 99.500(4)
_cell_angle_gamma                90
_cell_volume                     636.14(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    432
_cell_measurement_theta_min      2
_cell_measurement_theta_max      20

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             286
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.616614
_exptl_absorpt_correction_T_max  0.746082
_exptl_absorpt_process_details   twinabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1761
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         3.592
_diffrn_reflns_theta_max         30.578
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.450
_diffrn_reflns_point_group_measured_fraction_full 0.529
_reflns_number_total             1761
_reflns_number_gt                1547
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0316P)²+0.1668P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.041(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   -0.7(11)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         1761
_refine_ls_number_parameters     184
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.0787
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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_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
Li1 Li 0.0272(6) 0.6632(4) 0.6445(3) 0.0147(8) Uani 1 1 d . . . A 1
O2 O -0.0363(3) 0.52185(15) 0.53135(13) 0.0136(3) Uani 1 1 d . . . A 1
C3 C 0.0917(4) 0.4423(2) 0.48524(17) 0.0105(4) Uani 1 1 d . . . A 1
O4 O 0.0154(3) 0.33425(15) 0.44438(13) 0.0138(3) Uani 1 1 d . . . A 1
C5 C 0.3638(4) 0.4825(2) 0.47934(17) 0.0106(4) Uani 1 1 d . . . A 1
H5 H 0.4665 0.4774 0.5599 0.013 Uiso 1 1 calc R U . A 1
N6 N 0.4771(3) 0.39656(17) 0.39594(15) 0.0099(4) Uani 1 1 d . . . A 1
H6A H 0.3781 0.3262 0.3764 0.012 Uiso 1 1 calc R U . A 1
H6B H 0.6307 0.3687 0.4310 0.012 Uiso 1 1 calc R U . A 1
C7 C 0.4996(4) 0.4740(2) 0.28654(18) 0.0143(4) Uani 1 1 d . . . A 1
H7A H 0.4352 0.4244 0.2143 0.017 Uiso 1 1 calc R U . A 1
H7B H 0.6758 0.4981 0.2851 0.017 Uiso 1 1 calc R U . A 1
C8 C 0.3407(4) 0.5930(2) 0.29633(18) 0.0151(5) Uani 1 1 d . . . A 1
H8A H 0.1621 0.5759 0.2657 0.018 Uiso 1 1 calc R U . A 1
H8B H 0.3978 0.6670 0.2531 0.018 Uiso 1 1 calc R U . A 1
C9 C 0.3832(4) 0.6182(2) 0.42948(18) 0.0130(4) Uani 1 1 d . . . A 1
H9A H 0.5501 0.6564 0.4568 0.016 Uiso 1 1 calc R U . A 1
H9B H 0.2531 0.6760 0.4516 0.016 Uiso 1 1 calc R U . A 1
O10 O 0.3537(3) 0.67065(17) 0.72590(13) 0.0162(3) Uani 1 1 d . . . A 1
C11 C 0.5729(4) 0.6365(2) 0.76236(17) 0.0108(4) Uani 1 1 d . . . A 1
O12 O 0.7611(3) 0.68782(17) 0.72901(13) 0.0167(4) Uani 1 1 d . . . A 1
C13 C 0.6236(4) 0.5313(2) 0.85448(18) 0.0115(4) Uani 1 1 d . . . A 1
C14 C 0.8380(4) 0.5396(2) 0.9394(2) 0.0173(5) Uani 1 1 d . . . A 1
H14 H 0.9523 0.6086 0.9362 0.021 Uiso 1 1 calc R U . A 1
C15 C 0.8871(4) 0.4481(3) 1.02881(19) 0.0223(5) Uani 1 1 d . . . A 1
H15 H 1.0334 0.4551 1.0866 0.027 Uiso 1 1 calc R U . A 1
C16 C 0.7230(5) 0.3474(3) 1.0332(2) 0.0225(5) Uani 1 1 d . . . A 1
H16 H 0.7554 0.2857 1.0950 0.027 Uiso 1 1 calc R U . A 1
C17 C 0.5109(5) 0.3353(3) 0.9482(2) 0.0203(5) Uani 1 1 d . . . A 1
H17 H 0.4001 0.2646 0.9509 0.024 Uiso 1 1 calc R U . A 1
C18 C 0.4605(4) 0.4273(2) 0.85878(19) 0.0158(4) Uani 1 1 d . . . A 1
H18 H 0.3151 0.4192 0.8006 0.019 Uiso 0.067(5) 1 calc R U P B 1
O19 O 0.2623(3) 0.41823(18) 0.76747(15) 0.0216(5) Uani 0.933(5) 1 d . . P B 2
C20 C 0.0945(5) 0.3123(3) 0.7664(2) 0.0216(6) Uani 0.933(5) 1 d . . P B 2
H20A H 0.1851 0.2312 0.7606 0.032 Uiso 0.933(5) 1 calc R U P B 2
H20B H -0.0402 0.3203 0.6986 0.032 Uiso 0.933(5) 1 calc R U P B 2
H20C H 0.0232 0.3125 0.8394 0.032 Uiso 0.933(5) 1 calc R U P B 2


_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 O10 1.862(4) . ?
Li1 O12 1.885(4) 1_455 ?
Li1 O2 1.950(4) . ?
Li1 O4 2.037(4) 2_556 ?
O2 C3 1.250(3) . ?
C3 O4 1.256(3) . ?
C3 C5 1.545(3) . ?
O4 Li1 2.037(4) 2_546 ?
C5 N6 1.511(2) . ?
C5 C9 1.526(3) . ?
C5 H5 1.0000 . ?
N6 C7 1.513(3) . ?
N6 H6A 0.9100 . ?
N6 H6B 0.9100 . ?
C7 C8 1.517(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.533(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
O10 C11 1.244(3) . ?
C11 O12 1.265(3) . ?
C11 C13 1.512(3) . ?
O12 Li1 1.885(4) 1_655 ?
C13 C14 1.392(3) . ?
C13 C18 1.399(3) . ?
C14 C15 1.391(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.395(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
O19 C20 1.423(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
O10 Li1 O12 118.6(2) . 1_455 ?
O10 Li1 O2 114.5(2) . . ?
O12 Li1 O2 112.30(19) 1_455 . ?
O10 Li1 O4 103.65(18) . 2_556 ?
O12 Li1 O4 96.23(18) 1_455 2_556 ?
O2 Li1 O4 108.91(18) . 2_556 ?
C3 O2 Li1 136.70(18) . . ?
O2 C3 O4 124.96(19) . . ?
O2 C3 C5 116.26(19) . . ?
O4 C3 C5 118.78(18) . . ?
C3 O4 Li1 164.52(17) . 2_546 ?
N6 C5 C9 104.03(15) . . ?
N6 C5 C3 111.11(16) . . ?
C9 C5 C3 112.92(17) . . ?
N6 C5 H5 109.5 . . ?
C9 C5 H5 109.5 . . ?
C3 C5 H5 109.5 . . ?
C5 N6 C7 108.25(15) . . ?
C5 N6 H6A 110.0 . . ?
C7 N6 H6A 110.0 . . ?
C5 N6 H6B 110.0 . . ?
C7 N6 H6B 110.0 . . ?
H6A N6 H6B 108.4 . . ?
N6 C7 C8 104.08(16) . . ?
N6 C7 H7A 110.9 . . ?
C8 C7 H7A 110.9 . . ?
N6 C7 H7B 110.9 . . ?
C8 C7 H7B 110.9 . . ?
H7A C7 H7B 109.0 . . ?
C7 C8 C9 102.63(17) . . ?
C7 C8 H8A 111.2 . . ?
C9 C8 H8A 111.2 . . ?
C7 C8 H8B 111.2 . . ?
C9 C8 H8B 111.2 . . ?
H8A C8 H8B 109.2 . . ?
C5 C9 C8 102.17(18) . . ?
C5 C9 H9A 111.3 . . ?
C8 C9 H9A 111.3 . . ?
C5 C9 H9B 111.3 . . ?
C8 C9 H9B 111.3 . . ?
H9A C9 H9B 109.2 . . ?
C11 O10 Li1 158.9(2) . . ?
O10 C11 O12 123.5(2) . . ?
O10 C11 C13 119.57(18) . . ?
O12 C11 C13 116.91(18) . . ?
C11 O12 Li1 145.5(2) . 1_655 ?
C14 C13 C18 118.8(2) . . ?
C14 C13 C11 118.8(2) . . ?
C18 C13 C11 122.41(18) . . ?
C15 C14 C13 120.8(2) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.6(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C18 119.8(2) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C13 120.2(2) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
O19 C20 H20A 109.5 . . ?
O19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_1_1rt
_database_code_depnum_ccdc_archive 'CCDC 1845830'
_audit_update_record             
;
2018-07-26 deposited with the CCDC.
2018-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H14 Li N O4'
_chemical_formula_weight         243.18

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

_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'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   10.1119(18)
_cell_length_b                   10.5584(19)
_cell_length_c                   11.746(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1254.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    650
_cell_measurement_theta_min      2
_cell_measurement_theta_max      20

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7023
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31839
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.594
_diffrn_reflns_theta_max         30.652
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3869
_reflns_number_gt                2669
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    1.000

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0681P)²+0.3405P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 852 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3869
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0664
_refine_ls_wR_factor_ref         0.1516
_refine_ls_wR_factor_gt          0.1352
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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_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
O1 O 0.5016(3) 0.34947(19) 0.2917(2) 0.0445(6) Uani 1 1 d . . . . .
Li1 Li 0.5000 0.5000 0.3770(6) 0.0296(14) Uani 1 2 d S T P . .
C2 C 0.4493(3) 0.2568(3) 0.2435(2) 0.0257(6) Uani 1 1 d . . . . .
Li2 Li 0.5000 0.0000 0.3372(6) 0.0268(13) Uani 1 2 d S T P . .
O3 O 0.4926(3) 0.14757(18) 0.24958(19) 0.0411(6) Uani 1 1 d . . . . .
C4 C 0.3293(3) 0.2809(3) 0.1706(2) 0.0306(6) Uani 1 1 d . . . . .
C5 C 0.2859(4) 0.4030(4) 0.1511(3) 0.0520(10) Uani 1 1 d . . . . .
H5 H 0.3296 0.4705 0.1852 0.062 Uiso 1 1 calc R U . . .
C6 C 0.1785(4) 0.4262(5) 0.0817(4) 0.0722(14) Uani 1 1 d . . . . .
H6 H 0.1496 0.5088 0.0702 0.087 Uiso 1 1 calc R U . . .
C7 C 0.1157(4) 0.3290(6) 0.0308(4) 0.0769(16) Uani 1 1 d . . . . .
H7 H 0.0447 0.3452 -0.0174 0.092 Uiso 1 1 calc R U . . .
C8 C 0.1549(5) 0.2074(6) 0.0492(5) 0.0889(19) Uani 1 1 d . . . . .
H8 H 0.1099 0.1409 0.0146 0.107 Uiso 1 1 calc R U . . .
C9 C 0.2637(4) 0.1823(4) 0.1203(3) 0.0556(10) Uani 1 1 d . . . . .
H9 H 0.2908 0.0994 0.1330 0.067 Uiso 1 1 calc R U . . .
O10 O 0.6611(2) 0.4765(2) 0.4621(2) 0.0430(6) Uani 1 1 d . . . A 1
C11 C 0.7673(3) 0.4393(2) 0.5016(2) 0.0239(6) Uani 1 1 d . . . A 1
O12 O 0.84027(18) 0.5006(2) 0.56741(17) 0.0332(5) Uani 1 1 d . . . A 1
C13 C 0.8160(3) 0.3061(3) 0.4713(3) 0.0287(6) Uani 1 1 d . . . A 1
H13 H 0.8115 0.2533 0.5399 0.034 Uiso 1 1 calc R U . A 1
N14 N 0.7346(2) 0.2452(2) 0.38049(19) 0.0254(5) Uani 1 1 d . . . A 1
H14A H 0.7080 0.1689 0.4032 0.031 Uiso 1 1 calc R U . A 1
H14B H 0.6633 0.2920 0.3662 0.031 Uiso 1 1 calc R U . A 1
C15 C 0.8167(4) 0.2337(4) 0.2761(3) 0.0543(10) Uani 1 1 d . . . A 1
H15A H 0.7715 0.2679 0.2102 0.065 Uiso 1 1 calc R U . A 1
H15B H 0.8407 0.1463 0.2614 0.065 Uiso 1 1 calc R U . A 1
C16B C 0.9390(8) 0.3139(11) 0.3075(8) 0.069(3) Uani 0.573(12) 1 d . . P A 1
H16A H 1.0167 0.2830 0.2677 0.083 Uiso 0.573(12) 1 calc R U P A 1
H16B H 0.9251 0.4019 0.2870 0.083 Uiso 0.573(12) 1 calc R U P A 1
C16A C 0.9545(8) 0.2139(9) 0.3222(8) 0.042(3) Uani 0.427(12) 1 d . . P A 2
H2 H 0.962(6) 0.136(6) 0.339(5) 0.007(15) Uiso 0.427(12) 1 d . . P A 2
H3 H 1.031(8) 0.208(8) 0.282(7) 0.04(2) Uiso 0.427(12) 1 d . . P A 2
C17 C 0.9554(3) 0.3017(4) 0.4260(4) 0.0621(13) Uani 1 1 d . . . A 1
H17A H 1.0079 0.3708 0.4563 0.075 Uiso 1 1 calc R U . A 1
H17B H 0.9978 0.2221 0.4450 0.075 Uiso 1 1 calc R U . A 1


_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
O1 C2 1.248(3) . ?
O1 Li1 1.879(4) . ?
Li1 O1 1.879(4) 2_665 ?
Li1 O10 1.927(4) 2_665 ?
Li1 O10 1.927(4) . ?
C2 O3 1.235(3) . ?
C2 C4 1.507(4) . ?
Li2 O3 1.869(4) . ?
Li2 O3 1.869(4) 2_655 ?
Li2 O12 1.966(4) 4_646 ?
Li2 O12 1.966(4) 3_456 ?
C4 C9 1.369(5) . ?
C4 C5 1.381(5) . ?
C5 C6 1.379(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.347(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.361(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.406(6) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
O10 C11 1.234(3) . ?
C11 O12 1.250(3) . ?
C11 C13 1.532(4) . ?
O12 Li2 1.966(4) 3_556 ?
C13 N14 1.493(3) . ?
C13 C17 1.507(5) . ?
C13 H13 0.9800 . ?
N14 C15 1.486(4) . ?
N14 H14A 0.8900 . ?
N14 H14B 0.8900 . ?
C15 C16B 1.543(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16B C17 1.408(10) . ?
C16B H16A 0.9700 . ?
C16B H16B 0.9700 . ?
C16A H2 0.85(7) . ?
C16A H3 0.91(9) . ?
C17 H17A 0.9700 . ?
C17 H17B 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
C2 O1 Li1 154.3(2) . . ?
O1 Li1 O1 115.5(4) 2_665 . ?
O1 Li1 O10 99.22(9) 2_665 2_665 ?
O1 Li1 O10 113.14(11) . 2_665 ?
O1 Li1 O10 113.14(11) 2_665 . ?
O1 Li1 O10 99.22(9) . . ?
O10 Li1 O10 117.5(4) 2_665 . ?
O3 C2 O1 123.8(3) . . ?
O3 C2 C4 118.4(3) . . ?
O1 C2 C4 117.8(3) . . ?
O3 Li2 O3 113.2(4) . 2_655 ?
O3 Li2 O12 110.12(10) . 4_646 ?
O3 Li2 O12 106.48(10) 2_655 4_646 ?
O3 Li2 O12 106.48(10) . 3_456 ?
O3 Li2 O12 110.12(10) 2_655 3_456 ?
O12 Li2 O12 110.5(3) 4_646 3_456 ?
C2 O3 Li2 145.5(3) . . ?
C9 C4 C5 118.9(3) . . ?
C9 C4 C2 120.5(3) . . ?
C5 C4 C2 120.6(3) . . ?
C6 C5 C4 121.0(4) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C7 C6 C5 119.9(5) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.7(4) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C9 120.0(4) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C4 C9 C8 119.5(4) . . ?
C4 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 O10 Li1 166.3(2) . . ?
O10 C11 O12 125.5(3) . . ?
O10 C11 C13 119.0(2) . . ?
O12 C11 C13 115.4(2) . . ?
C11 O12 Li2 146.7(2) . 3_556 ?
N14 C13 C17 104.5(3) . . ?
N14 C13 C11 112.6(2) . . ?
C17 C13 C11 114.3(3) . . ?
N14 C13 H13 108.4 . . ?
C17 C13 H13 108.4 . . ?
C11 C13 H13 108.4 . . ?
C15 N14 C13 108.4(2) . . ?
C15 N14 H14A 110.0 . . ?
C13 N14 H14A 110.0 . . ?
C15 N14 H14B 110.0 . . ?
C13 N14 H14B 110.0 . . ?
H14A N14 H14B 108.4 . . ?
N14 C15 C16B 101.9(4) . . ?
N14 C15 H15A 111.4 . . ?
C16B C15 H15A 111.4 . . ?
N14 C15 H15B 111.4 . . ?
C16B C15 H15B 111.4 . . ?
H15A C15 H15B 109.3 . . ?
C17 C16B C15 106.3(6) . . ?
C17 C16B H16A 110.5 . . ?
C15 C16B H16A 110.5 . . ?
C17 C16B H16B 110.5 . . ?
C15 C16B H16B 110.5 . . ?
H16A C16B H16B 108.7 . . ?
H2 C16A H3 89(6) . . ?
C16B C17 C13 103.7(4) . . ?
C16B C17 H17A 111.0 . . ?
C13 C17 H17A 111.0 . . ?
C16B C17 H17B 111.0 . . ?
C13 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.051


# start Validation Reply Form
_vrf_PLAT410_E_1_1rt             
;
PROBLEM: Short Intra H...H Contact  H15B     ..H2               1.53 Ang.  
RESPONSE: those are disordered atoms
;
# end Validation Reply Form



####################################################################### 
# 
# 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_1_090
_database_code_depnum_ccdc_archive 'CCDC 1845834'
_audit_update_record             
;
2018-05-28 deposited with the CCDC.
2018-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8.05 H9.44 Li0.67 N0.67 O2.72'
_chemical_formula_weight         163.67

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

_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'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   10.0666(9)
_cell_length_b                   10.5869(8)
_cell_length_c                   11.7836(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1255.83(17)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    452
_cell_measurement_theta_min      2
_cell_measurement_theta_max      20

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             517
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6317
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4580
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.586
_diffrn_reflns_theta_max         23.263
_diffrn_reflns_theta_full        23.263
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             1777
_reflns_number_gt                1720
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_max     0.984
_reflns_Friedel_fraction_full    0.985

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0507P)²+1.1776P] 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_abs_structure_details 
;
 Flack x determined using 681 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(7)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         1777
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1293
_refine_ls_wR_factor_gt          0.1282
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_restrained_S_all      1.154
_refine_ls_shift/su_max          0.456
_refine_ls_shift/su_mean         0.016

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
O1 O 0.1587(3) -0.0020(3) 0.4260(2) 0.0177(7) Uani 1 1 d . . . . .
Li1 Li 0.0000 0.0000 0.3294(8) 0.018(2) Uani 1 2 d S T P . .
C2 C 0.2328(4) -0.0626(4) 0.4928(3) 0.0135(9) Uani 1 1 d . . . . .
Li2 Li 0.0000 0.5000 0.3831(8) 0.016(2) Uani 1 2 d S T P . .
O3 O 0.3388(3) -0.0238(3) 0.5336(3) 0.0226(7) Uani 1 1 d . . . . .
C4 C 0.1838(4) -0.1972(4) 0.5233(3) 0.0169(9) Uani 1 1 d . . . . .
H4 H 0.1894 -0.2517 0.4542 0.020 Uiso 1 1 calc R U . . .
N5 N 0.2654(3) -0.2560(3) 0.6165(3) 0.0147(8) Uani 1 1 d . . . . .
H5A H 0.2916 -0.3350 0.5958 0.018 Uiso 1 1 calc R U . . .
H5B H 0.3392 -0.2086 0.6298 0.018 Uiso 1 1 calc R U . . .
C6 C 0.1816(5) -0.2626(5) 0.7219(4) 0.0274(11) Uani 1 1 d . . . . .
H6A H 0.2303 -0.2284 0.7882 0.033 Uiso 1 1 calc R U . . .
H6B H 0.1550 -0.3507 0.7383 0.033 Uiso 1 1 calc R U . . .
C7 C 0.0609(6) -0.1815(6) 0.6942(5) 0.0459(15) Uani 1 1 d . . . . .
H7A H -0.0182 -0.2100 0.7371 0.055 Uiso 1 1 calc R U . . .
H7B H 0.0779 -0.0915 0.7118 0.055 Uiso 1 1 calc R U . . .
C8 C 0.0422(4) -0.2010(5) 0.5688(4) 0.0279(11) Uani 1 1 d . . . . .
H8A H -0.0125 -0.1328 0.5353 0.034 Uiso 1 1 calc R U . . .
H8B H -0.0002 -0.2835 0.5529 0.034 Uiso 1 1 calc R U . . .
O9 O -0.0061(3) 0.1490(3) 0.2426(2) 0.0208(7) Uani 1 1 d . . . . .
C10 C -0.0502(4) 0.2593(4) 0.2419(3) 0.0153(9) Uani 1 1 d . . . . .
O11 O 0.0019(3) 0.3490(3) 0.2970(2) 0.0231(7) Uani 1 1 d . . . . .
C12 C -0.1707(4) 0.2888(4) 0.1694(3) 0.0179(10) Uani 1 1 d . . . . .
C13 C -0.2400(5) 0.1921(5) 0.1171(4) 0.0323(12) Uani 1 1 d . . . A 1
H13 H -0.2147 0.1067 0.1292 0.039 Uiso 0.910(15) 1 calc R U P B 1
C14 C -0.3475(5) 0.2208(6) 0.0463(5) 0.0442(15) Uani 1 1 d . . . A 1
H14 H -0.3955 0.1544 0.0108 0.053 Uiso 1 1 calc R U . A 1
C15 C -0.3841(5) 0.3438(6) 0.0278(4) 0.0416(15) Uani 1 1 d . . . . .
H15 H -0.4561 0.3627 -0.0216 0.050 Uiso 1 1 calc R U . A 1
C16 C -0.3159(5) 0.4405(5) 0.0812(4) 0.0365(13) Uani 1 1 d . . . . .
H16 H -0.3423 0.5257 0.0697 0.044 Uiso 1 1 calc R U . . .
C17 C -0.2095(5) 0.4137(5) 0.1513(4) 0.0274(11) Uani 1 1 d . . . . .
H17 H -0.1627 0.4805 0.1873 0.033 Uiso 1 1 calc R U . . .
O18 O -0.262(7) 0.096(7) 0.173(6) 0.10(3) Uiso 0.090(15) 1 d . . P B 2
C19 C -0.413(13) 0.047(14) 0.132(13) 0.14(6) Uiso 0.090(15) 1 d . . P B 2
H19A H -0.4752 0.1181 0.1337 0.210 Uiso 0.090(15) 1 calc R U P B 2
H19B H -0.4445 -0.0195 0.1834 0.210 Uiso 0.090(15) 1 calc R U P B 2
H19C H -0.4084 0.0131 0.0545 0.210 Uiso 0.090(15) 1 calc R U P B 2


_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
O1 C2 1.260(5) . ?
O1 Li1 1.962(6) . ?
Li1 O9 1.881(6) 2 ?
Li1 O9 1.881(6) . ?
Li1 O1 1.962(6) 2 ?
C2 O3 1.241(5) . ?
C2 C4 1.550(6) . ?
Li2 O11 1.894(6) 2_565 ?
Li2 O11 1.894(6) . ?
Li2 O3 1.913(5) 4_556 ?
Li2 O3 1.913(5) 3_456 ?
O3 Li2 1.913(5) 3_556 ?
C4 N5 1.506(5) . ?
C4 C8 1.523(6) . ?
N5 C6 1.503(6) . ?
C6 C7 1.524(8) . ?
C7 C8 1.504(8) . ?
O9 C10 1.249(5) . ?
C10 O11 1.264(5) . ?
C10 C12 1.516(6) . ?
C12 C13 1.384(7) . ?
C12 C17 1.395(7) . ?
C13 C14 1.400(7) . ?
C14 C15 1.372(9) . ?
C15 C16 1.384(8) . ?
C16 C17 1.382(7) . ?
O18 C19 1.68(14) . ?
C19 C19 2.0(3) 2_455 ?

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
C2 O1 Li1 148.2(3) . . ?
O9 Li1 O9 114.1(5) 2 . ?
O9 Li1 O1 110.57(13) 2 2 ?
O9 Li1 O1 106.25(13) . 2 ?
O9 Li1 O1 106.25(13) 2 . ?
O9 Li1 O1 110.56(13) . . ?
O1 Li1 O1 109.0(5) 2 . ?
O3 C2 O1 125.6(4) . . ?
O3 C2 C4 119.2(4) . . ?
O1 C2 C4 115.1(3) . . ?
O11 Li2 O11 115.2(5) 2_565 . ?
O11 Li2 O3 113.24(13) 2_565 4_556 ?
O11 Li2 O3 98.92(13) . 4_556 ?
O11 Li2 O3 98.92(12) 2_565 3_456 ?
O11 Li2 O3 113.24(13) . 3_456 ?
O3 Li2 O3 118.3(5) 4_556 3_456 ?
C2 O3 Li2 166.5(3) . 3_556 ?
N5 C4 C8 104.0(3) . . ?
N5 C4 C2 112.1(3) . . ?
C8 C4 C2 113.8(3) . . ?
C6 N5 C4 108.4(3) . . ?
N5 C6 C7 104.1(4) . . ?
C8 C7 C6 103.5(4) . . ?
C7 C8 C4 103.0(4) . . ?
C10 O9 Li1 143.0(3) . . ?
O9 C10 O11 123.5(4) . . ?
O9 C10 C12 118.7(4) . . ?
O11 C10 C12 117.8(3) . . ?
C10 O11 Li2 154.8(3) . . ?
C13 C12 C17 119.4(4) . . ?
C13 C12 C10 120.1(4) . . ?
C17 C12 C10 120.4(4) . . ?
C12 C13 C14 119.7(5) . . ?
C15 C14 C13 120.6(5) . . ?
C14 C15 C16 119.8(5) . . ?
C17 C16 C15 120.3(5) . . ?
C16 C17 C12 120.2(5) . . ?
O18 C19 C19 160(9) . 2_455 ?

_refine_diff_density_max         0.832
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.057


# start Validation Reply Form
_vrf_SHFSU01_C_1_090             
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.20
RESPONSE: The shift involves the H atoms in the methoxy group
;
_vrf_THETM01_C_1_090             
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: weak reflection at high angles
;
_vrf_PLAT080_C_1_090             
;
PROBLEM: Maximum Shift/Error ............................       0.46 Why ? 
RESPONSE: The shift involves the H atoms in the methoxy group
;
_vrf_PLAT412_C_1_090             
;
PROBLEM: Short Intra XH3 .. XHn     H14      ..H19C             1.59 Ang.  
RESPONSE: these are the H atoms in the methoxy group
;
_vrf_PLAT097_C_1_090             
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.83 eA-3  
RESPONSE: ...
;
_vrf_PLAT220_C_1_090             
;
PROBLEM: Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range       10.0 Ratio 
RESPONSE: this is the methoxy group
;
_vrf_PLAT413_C_1_090             
;
PROBLEM: Short Inter XH3 .. XHn     H6B      ..H19B             1.93 Ang.  
RESPONSE: these are the H atoms in the methoxy group
;
# end Validation Reply Form
####################################################################### 
# 
# 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_1_000
_database_code_depnum_ccdc_archive 'CCDC 1845832'
_audit_update_record             
;
2018-05-28 deposited with the CCDC.
2018-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H16 Li N O5'
_chemical_formula_weight         273.21

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   5.4170(3)
_cell_length_b                   10.3590(6)
_cell_length_c                   11.4916(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.5520(10)
_cell_angle_gamma                90
_cell_volume                     635.91(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    67
_cell_measurement_theta_min      2
_cell_measurement_theta_max      20

_exptl_crystal_description       prism
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6989
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10425
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.664
_diffrn_reflns_theta_max         23.316
_diffrn_reflns_theta_full        23.316
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1816
_reflns_number_gt                1780
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.876
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.998

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0270P)²+0.0914P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.077(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 819 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         1816
_refine_ls_number_parameters     183
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0200
_refine_ls_R_factor_gt           0.0192
_refine_ls_wR_factor_ref         0.0484
_refine_ls_wR_factor_gt          0.0479
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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_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
O1 O 1.0362(2) 0.52094(13) 0.46871(12) 0.0148(3) Uani 1 1 d . . . . .
Li1 Li 0.9725(6) 0.6623(3) 0.3558(3) 0.0162(7) Uani 1 1 d . . . . .
C2 C 0.9075(4) 0.44140(19) 0.51452(16) 0.0124(4) Uani 1 1 d . . . . .
O3 O 0.9839(3) 0.33322(13) 0.55486(12) 0.0150(3) Uani 1 1 d . . . . .
C4 C 0.6364(4) 0.48145(18) 0.52008(17) 0.0122(5) Uani 1 1 d . . . . .
H4 H 0.5338 0.4764 0.4394 0.015 Uiso 1 1 calc R U . . .
N5 N 0.5223(3) 0.39588(15) 0.60358(14) 0.0117(4) Uani 1 1 d . . . . .
H5A H 0.3683 0.3684 0.5684 0.014 Uiso 1 1 calc R U . . .
H5B H 0.6207 0.3254 0.6231 0.014 Uiso 1 1 calc R U . . .
C6 C 0.5006(4) 0.47257(19) 0.71265(17) 0.0149(5) Uani 1 1 d . . . . .
H6A H 0.5658 0.4229 0.7848 0.018 Uiso 1 1 calc R U . . .
H6B H 0.3242 0.4965 0.7143 0.018 Uiso 1 1 calc R U . . .
C7 C 0.6588(4) 0.5916(2) 0.70285(17) 0.0157(5) Uani 1 1 d . . . . .
H7A H 0.8376 0.5749 0.7336 0.019 Uiso 1 1 calc R U . . .
H7B H 0.6011 0.6655 0.7460 0.019 Uiso 1 1 calc R U . . .
C8 C 0.6164(4) 0.6164(2) 0.57020(18) 0.0145(4) Uani 1 1 d . . . . .
H8A H 0.4491 0.6543 0.5428 0.017 Uiso 1 1 calc R U . . .
H8B H 0.7461 0.6745 0.5481 0.017 Uiso 1 1 calc R U . . .
O9 O 0.6463(2) 0.67116(14) 0.27370(11) 0.0159(3) Uani 1 1 d . . . . .
C10 C 0.4273(4) 0.63639(18) 0.23794(17) 0.0123(5) Uani 1 1 d . . . . .
O11 O 0.2393(2) 0.68712(14) 0.27149(12) 0.0174(4) Uani 1 1 d . . . . .
C12 C 0.3765(4) 0.53150(19) 0.14583(17) 0.0126(4) Uani 1 1 d . . . . .
C13 C 0.5381(4) 0.4264(2) 0.14168(17) 0.0148(4) Uani 1 1 d . . . . .
C14 C 0.4864(4) 0.3356(2) 0.05150(18) 0.0196(5) Uani 1 1 d . . . . .
H14 H 0.5964 0.2646 0.0486 0.024 Uiso 1 1 calc R U . . .
C15 C 0.2761(4) 0.3483(2) -0.03362(18) 0.0215(5) Uani 1 1 d . . . . .
H15 H 0.2433 0.2868 -0.0956 0.026 Uiso 1 1 calc R U . . .
C16 C 0.1130(4) 0.4500(2) -0.02917(17) 0.0209(5) Uani 1 1 d . . . . .
H16 H -0.0328 0.4579 -0.0874 0.025 Uiso 1 1 calc R U . . .
C17 C 0.1628(4) 0.5401(2) 0.06041(18) 0.0179(5) Uani 1 1 d . . . . .
H17 H 0.0489 0.6092 0.0637 0.022 Uiso 1 1 calc R U . . .
O18 O 0.7364(3) 0.41750(15) 0.23184(12) 0.0222(4) Uani 1 1 d . . . . .
C19 C 0.9047(4) 0.3120(2) 0.2324(2) 0.0221(5) Uani 1 1 d . . . . .
H19A H 0.8144 0.2308 0.2379 0.033 Uiso 1 1 calc R U . . .
H19B H 1.0396 0.3198 0.3003 0.033 Uiso 1 1 calc R U . . .
H19C H 0.9759 0.3127 0.1594 0.033 Uiso 1 1 calc R 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
O1 C2 1.251(2) . ?
O1 Li1 1.949(4) . ?
Li1 O9 1.862(3) . ?
Li1 O11 1.886(3) 1_655 ?
Li1 O3 2.041(4) 2_756 ?
C2 O3 1.256(3) . ?
C2 C4 1.537(3) . ?
O3 Li1 2.041(4) 2_746 ?
C4 N5 1.512(2) . ?
C4 C8 1.523(3) . ?
C4 H4 1.0000 . ?
N5 C6 1.505(2) . ?
N5 H5A 0.9100 . ?
N5 H5B 0.9100 . ?
C6 C7 1.517(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.525(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
O9 C10 1.243(2) . ?
C10 O11 1.262(2) . ?
C10 C12 1.510(3) . ?
O11 Li1 1.886(3) 1_455 ?
C12 C17 1.391(3) . ?
C12 C13 1.402(3) . ?
C13 O18 1.366(2) . ?
C13 C14 1.394(3) . ?
C14 C15 1.379(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
O18 C19 1.423(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C2 O1 Li1 136.54(16) . . ?
O9 Li1 O11 118.43(18) . 1_655 ?
O9 Li1 O1 115.01(19) . . ?
O11 Li1 O1 112.24(17) 1_655 . ?
O9 Li1 O3 103.47(16) . 2_756 ?
O11 Li1 O3 96.05(16) 1_655 2_756 ?
O1 Li1 O3 108.93(16) . 2_756 ?
O1 C2 O3 124.78(18) . . ?
O1 C2 C4 116.28(17) . . ?
O3 C2 C4 118.93(17) . . ?
C2 O3 Li1 164.40(16) . 2_746 ?
N5 C4 C8 103.65(15) . . ?
N5 C4 C2 111.22(15) . . ?
C8 C4 C2 113.08(16) . . ?
N5 C4 H4 109.6 . . ?
C8 C4 H4 109.6 . . ?
C2 C4 H4 109.6 . . ?
C6 N5 C4 108.41(14) . . ?
C6 N5 H5A 110.0 . . ?
C4 N5 H5A 110.0 . . ?
C6 N5 H5B 110.0 . . ?
C4 N5 H5B 110.0 . . ?
H5A N5 H5B 108.4 . . ?
N5 C6 C7 104.14(15) . . ?
N5 C6 H6A 110.9 . . ?
C7 C6 H6A 110.9 . . ?
N5 C6 H6B 110.9 . . ?
C7 C6 H6B 110.9 . . ?
H6A C6 H6B 108.9 . . ?
C6 C7 C8 102.57(16) . . ?
C6 C7 H7A 111.3 . . ?
C8 C7 H7A 111.3 . . ?
C6 C7 H7B 111.3 . . ?
C8 C7 H7B 111.3 . . ?
H7A C7 H7B 109.2 . . ?
C4 C8 C7 102.43(16) . . ?
C4 C8 H8A 111.3 . . ?
C7 C8 H8A 111.3 . . ?
C4 C8 H8B 111.3 . . ?
C7 C8 H8B 111.3 . . ?
H8A C8 H8B 109.2 . . ?
C10 O9 Li1 157.93(17) . . ?
O9 C10 O11 123.57(18) . . ?
O9 C10 C12 119.56(17) . . ?
O11 C10 C12 116.82(17) . . ?
C10 O11 Li1 145.70(18) . 1_455 ?
C17 C12 C13 118.47(19) . . ?
C17 C12 C10 118.83(19) . . ?
C13 C12 C10 122.69(18) . . ?
O18 C13 C14 123.62(18) . . ?
O18 C13 C12 116.33(17) . . ?
C14 C13 C12 120.01(18) . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.31(19) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 119.70(19) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C12 121.3(2) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
C13 O18 C19 118.57(16) . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         0.102
_refine_diff_density_min         -0.108
_refine_diff_density_rms         0.028


# start Validation Reply Form
_vrf_THETM01_C_1_0               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: The crystal did not diffract at high angle
;
_vrf_PLAT089_C_1_0               
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       5.29 Note  
RESPONSE: The crystal did not diffract at high angle
;
# end Validation Reply Form
####################################################################### 
# 
# 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_1_100
_database_code_depnum_ccdc_archive 'CCDC 1845833'
_audit_update_record             
;
2018-05-28 deposited with the CCDC.
2018-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H14 Li N O4'
_chemical_formula_weight         243.18

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

_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'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   10.0679(5)
_cell_length_b                   10.5702(6)
_cell_length_c                   11.7537(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1250.83(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    512
_cell_measurement_theta_min      2
_cell_measurement_theta_max      20

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6351
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11648
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.592
_diffrn_reflns_theta_max         30.652
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.826
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3200
_reflns_number_gt                3066
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.661
_reflns_Friedel_fraction_max     0.767
_reflns_Friedel_fraction_full    0.985

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0686P)²+0.6380P] 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_abs_structure_details 
;
 Flack x determined using 1210 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3200
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1268
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_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_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
Li1 Li 0.5000 0.5000 0.6170(4) 0.0132(9) Uani 1 2 d S T P . .
O2 O 0.33844(16) 0.47556(15) 0.53365(15) 0.0185(4) Uani 1 1 d . . . . .
C3 C 0.2319(2) 0.43658(19) 0.49302(17) 0.0115(4) Uani 1 1 d . . . . .
O4 O 0.15798(14) 0.49741(15) 0.42609(12) 0.0134(3) Uani 1 1 d . . . . .
C5 C 0.1837(2) 0.30176(19) 0.52331(17) 0.0119(4) Uani 1 1 d . . . . .
H5 H 0.1895 0.2470 0.4541 0.014 Uiso 1 1 calc R U . . .
N6 N 0.26572(17) 0.24403(16) 0.61667(15) 0.0112(3) Uani 1 1 d . . . . .
H6A H 0.3392 0.2920 0.6295 0.013 Uiso 1 1 calc R U . . .
H6B H 0.2925 0.1651 0.5961 0.013 Uiso 1 1 calc R U . . .
C7 C 0.1826(2) 0.2372(2) 0.72326(19) 0.0199(5) Uani 1 1 d . . . . .
H7A H 0.2318 0.2709 0.7896 0.024 Uiso 1 1 calc R U . . .
H7B H 0.1555 0.1490 0.7395 0.024 Uiso 1 1 calc R U . . .
C8 C 0.0618(3) 0.3197(3) 0.6956(2) 0.0284(6) Uani 1 1 d . . . . .
H8A H -0.0171 0.2924 0.7395 0.034 Uiso 1 1 calc R U . . .
H8B H 0.0799 0.4099 0.7121 0.034 Uiso 1 1 calc R U . . .
C9 C 0.0419(2) 0.2982(2) 0.5691(2) 0.0203(5) Uani 1 1 d . . . . .
H9A H -0.0131 0.3659 0.5350 0.024 Uiso 1 1 calc R U . . .
H9B H -0.0004 0.2153 0.5542 0.024 Uiso 1 1 calc R U . . .
O10 O 0.50270(18) 0.65076(15) 0.70296(13) 0.0177(3) Uani 1 1 d . . . . .
C11 C 0.4507(2) 0.74082(18) 0.75832(17) 0.0106(4) Uani 1 1 d . . . . .
O12 O 0.49382(17) 0.85142(14) 0.75772(13) 0.0160(3) Uani 1 1 d . . . . .
C13 C 0.3303(2) 0.7107(2) 0.83087(17) 0.0130(4) Uani 1 1 d . . . . .
C14 C 0.2605(2) 0.8087(2) 0.8837(2) 0.0208(5) Uani 1 1 d . . . . .
H14 H 0.2854 0.8942 0.8710 0.025 Uiso 1 1 calc R U . . .
C15 C 0.1537(3) 0.7802(3) 0.9553(2) 0.0278(6) Uani 1 1 d . . . . .
H15 H 0.1067 0.8466 0.9920 0.033 Uiso 1 1 calc R U . . .
C16 C 0.1159(2) 0.6560(3) 0.9730(2) 0.0273(6) Uani 1 1 d . . . . .
H16 H 0.0438 0.6372 1.0224 0.033 Uiso 1 1 calc R U . . .
C17 C 0.1834(2) 0.5585(2) 0.9184(2) 0.0231(5) Uani 1 1 d . . . . .
H17 H 0.1563 0.4733 0.9293 0.028 Uiso 1 1 calc R U . . .
C18 C 0.2910(2) 0.5859(2) 0.8477(2) 0.0182(5) Uani 1 1 d . . . . .
H18 H 0.3375 0.5192 0.8110 0.022 Uiso 1 1 calc R U . . .
Li19 Li 0.5000 1.0000 0.6711(4) 0.0135(9) Uani 1 2 d S T P . .


_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 O10 1.887(3) 2_665 ?
Li1 O10 1.887(3) . ?
Li1 O2 1.917(3) 2_665 ?
Li1 O2 1.917(3) . ?
O2 C3 1.244(3) . ?
C3 O4 1.260(2) . ?
C3 C5 1.547(3) . ?
O4 Li19 1.958(3) 3_466 ?
C5 N6 1.503(3) . ?
C5 C9 1.526(3) . ?
C5 H5 1.0000 . ?
N6 C7 1.509(3) . ?
N6 H6A 0.9100 . ?
N6 H6B 0.9100 . ?
C7 C8 1.531(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.518(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
O10 C11 1.267(2) . ?
C11 O12 1.247(2) . ?
C11 C13 1.515(3) . ?
O12 Li19 1.873(3) . ?
C13 C18 1.391(3) . ?
C13 C14 1.398(3) . ?
C14 C15 1.398(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.396(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
Li19 O12 1.873(3) 2_675 ?
Li19 O4 1.958(3) 4_556 ?
Li19 O4 1.958(3) 3_566 ?

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
O10 Li1 O10 115.3(3) 2_665 . ?
O10 Li1 O2 113.56(7) 2_665 2_665 ?
O10 Li1 O2 98.49(7) . 2_665 ?
O10 Li1 O2 98.49(7) 2_665 . ?
O10 Li1 O2 113.57(7) . . ?
O2 Li1 O2 118.5(3) 2_665 . ?
C3 O2 Li1 166.53(17) . . ?
O2 C3 O4 125.46(19) . . ?
O2 C3 C5 119.16(18) . . ?
O4 C3 C5 115.37(17) . . ?
C3 O4 Li19 148.37(15) . 3_466 ?
N6 C5 C9 104.27(16) . . ?
N6 C5 C3 111.69(16) . . ?
C9 C5 C3 113.42(17) . . ?
N6 C5 H5 109.1 . . ?
C9 C5 H5 109.1 . . ?
C3 C5 H5 109.1 . . ?
C5 N6 C7 108.72(16) . . ?
C5 N6 H6A 109.9 . . ?
C7 N6 H6A 109.9 . . ?
C5 N6 H6B 109.9 . . ?
C7 N6 H6B 109.9 . . ?
H6A N6 H6B 108.3 . . ?
N6 C7 C8 103.72(18) . . ?
N6 C7 H7A 111.0 . . ?
C8 C7 H7A 111.0 . . ?
N6 C7 H7B 111.0 . . ?
C8 C7 H7B 111.0 . . ?
H7A C7 H7B 109.0 . . ?
C9 C8 C7 103.1(2) . . ?
C9 C8 H8A 111.1 . . ?
C7 C8 H8A 111.1 . . ?
C9 C8 H8B 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
C8 C9 C5 102.62(18) . . ?
C8 C9 H9A 111.2 . . ?
C5 C9 H9A 111.2 . . ?
C8 C9 H9B 111.2 . . ?
C5 C9 H9B 111.2 . . ?
H9A C9 H9B 109.2 . . ?
C11 O10 Li1 154.67(16) . . ?
O12 C11 O10 123.9(2) . . ?
O12 C11 C13 118.60(18) . . ?
O10 C11 C13 117.51(18) . . ?
C11 O12 Li19 143.19(18) . . ?
C18 C13 C14 119.7(2) . . ?
C18 C13 C11 120.46(19) . . ?
C14 C13 C11 119.8(2) . . ?
C13 C14 C15 119.6(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 120.2(2) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
O12 Li19 O12 114.1(3) . 2_675 ?
O12 Li19 O4 106.16(7) . 4_556 ?
O12 Li19 O4 110.85(7) 2_675 4_556 ?
O12 Li19 O4 110.85(7) . 3_566 ?
O12 Li19 O4 106.16(7) 2_675 3_566 ?
O4 Li19 O4 108.7(2) 4_556 3_566 ?

_refine_diff_density_max         1.030
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.069

# start Validation Reply Form
_vrf_PLAT097_C_1_1               
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.03 eA-3  
RESPONSE: it is due to disorder in the conformation of the proline ring 
;
_vrf_PLAT919_C_1_1               
;
PROBLEM: Reflection # Likely Affected by the Beamstop ...          2 Check 
RESPONSE: this is due to the beamstop position
;
_vrf_PLAT934_C_1_1               
;
PROBLEM: Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          2 Check 
RESPONSE: this is due to the beamstop position
;
# end Validation Reply Form
