# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_La_NO3_B_CN4_H2O
_database_code_depnum_ccdc_archive 'CCDC 1532972'
_audit_update_record             
;
2017-02-15 deposited with the CCDC.
2017-04-20 downloaded from the CCDC.
;
_audit_creation_date             2015-04-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H8 B La N6 O10'
_chemical_formula_sum            'C4 H8 B La N6 O10'
_chemical_formula_weight         449.88
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
La La -0.2871 2.4523 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        ' P21/c '
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.902(2)
_cell_length_b                   11.629(2)
_cell_length_c                   10.850(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.77(3)
_cell_angle_gamma                90
_cell_volume                     1394.7(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.820
_cell_measurement_theta_min      2.542
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.126
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0604 before and 0.0403 after correction.
The Ratio of minimum to maximum transmission is 0.8387.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.143
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.131
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.059
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18300
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.542
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2704
_reflns_number_total             3061
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.809
_refine_diff_density_min         -0.863
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3061
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0202
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0195P)²+2.2769P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0443
_refine_ls_wR_factor_ref         0.0460
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O9(H9A,H9B), O8(H8A,H8B), O10(H10A,H10B), O7(H7A,H7B)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
La1 La 0.21435(2) 0.58316(2) 0.30968(2) 0.00678(5) Uani 1 1 d . . . . .
O2 O 0.35287(16) 0.71406(16) 0.23274(18) 0.0117(4) Uani 1 1 d . . . . .
O5 O -0.01601(17) 0.67834(17) 0.18575(18) 0.0151(4) Uani 1 1 d . . . . .
O9 O 0.19521(16) 0.78727(15) 0.38217(18) 0.0113(4) Uani 1 1 d . . . . .
H9A H 0.2663 0.8225 0.4118 0.017 Uiso 1 1 d GR . . . .
H9B H 0.1666 0.7878 0.4468 0.017 Uiso 1 1 d GR . . . .
O8 O 0.09091(16) 0.56794(16) 0.45214(18) 0.0124(4) Uani 1 1 d . . . . .
H8A H 0.0739 0.4976 0.4591 0.019 Uiso 1 1 d GR . . . .
H8B H 0.0255 0.6060 0.4168 0.019 Uiso 1 1 d GR . . . .
O10 O 0.35755(17) 0.60047(16) 0.55183(18) 0.0133(4) Uani 1 1 d . . . . .
H10A H 0.4059 0.5436 0.5719 0.020 Uiso 1 1 d GR . . . .
H10B H 0.3166 0.6008 0.6015 0.020 Uiso 1 1 d GR . . . .
O1 O 0.44759(17) 0.56530(16) 0.34280(18) 0.0139(4) Uani 1 1 d . . . . .
O4 O 0.11034(16) 0.68182(17) 0.08587(18) 0.0139(4) Uani 1 1 d . . . . .
O7 O 0.04159(17) 0.43850(17) 0.19827(19) 0.0172(4) Uani 1 1 d . . . . .
H7A H -0.0341 0.4436 0.1985 0.026 Uiso 1 1 d GR . . . .
H7B H 0.0474 0.3751 0.1531 0.026 Uiso 1 1 d GR . . . .
O3 O 0.54855(17) 0.70141(18) 0.29022(19) 0.0163(4) Uani 1 1 d . . . . .
O6 O -0.06826(17) 0.75745(18) -0.00938(19) 0.0191(4) Uani 1 1 d . . . . .
N6 N 0.0057(2) 0.70728(19) 0.0858(2) 0.0107(5) Uani 1 1 d . . . . .
N5 N 0.4538(2) 0.6611(2) 0.2889(2) 0.0114(5) Uani 1 1 d . . . . .
N2 N 0.1999(2) 0.0267(2) 0.2061(2) 0.0157(5) Uani 1 1 d . . . . .
N4 N 0.5703(2) 0.1284(2) 0.5179(2) 0.0137(5) Uani 1 1 d . . . . .
N3 N 0.2530(2) 0.0404(2) 0.6197(2) 0.0128(5) Uani 1 1 d . . . . .
N1 N 0.2783(2) 0.3733(2) 0.3979(2) 0.0128(5) Uani 1 1 d . . . . .
C3 C 0.2824(2) 0.0879(2) 0.5448(3) 0.0096(5) Uani 1 1 d . . . . .
C1 C 0.2934(2) 0.2772(2) 0.4146(2) 0.0107(5) Uani 1 1 d . . . . .
C2 C 0.2551(2) 0.0766(2) 0.2992(3) 0.0105(5) Uani 1 1 d . . . . .
C4 C 0.4677(2) 0.1327(2) 0.4812(2) 0.0098(5) Uani 1 1 d . . . . .
B1 B 0.3244(3) 0.1437(3) 0.4345(3) 0.0092(6) 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
La1 O2 2.5987(18) . ?
La1 O5 2.796(2) . ?
La1 O9 2.5373(18) . ?
La1 O8 2.5028(18) . ?
La1 O10 2.555(2) . ?
La1 O1 2.6719(19) . ?
La1 O4 2.5527(19) . ?
La1 O7 2.584(2) . ?
La1 N3 2.689(2) 4_565 ?
La1 N1 2.629(2) . ?
O2 N5 1.285(3) . ?
O5 N6 1.250(3) . ?
O9 H9A 0.8862 . ?
O9 H9B 0.8860 . ?
O8 H8A 0.8530 . ?
O8 H8B 0.8533 . ?
O10 H10A 0.8497 . ?
O10 H10B 0.8504 . ?
O1 N5 1.273(3) . ?
O4 N6 1.280(3) . ?
O7 H7A 0.9031 . ?
O7 H7B 0.9027 . ?
O3 N5 1.216(3) . ?
O6 N6 1.228(3) . ?
N2 C2 1.140(4) . ?
N4 C4 1.137(3) . ?
N3 La1 2.689(2) 4_566 ?
N3 C3 1.139(3) . ?
N1 C1 1.135(3) . ?
C3 B1 1.595(4) . ?
C1 B1 1.592(4) . ?
C2 B1 1.595(4) . ?
C4 B1 1.593(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
O2 La1 O5 103.85(6) . . ?
O2 La1 O1 48.50(6) . . ?
O2 La1 N3 75.95(7) . 4_565 ?
O2 La1 N1 121.87(6) . . ?
O9 La1 O2 72.07(6) . . ?
O9 La1 O5 66.04(6) . . ?
O9 La1 O10 73.13(6) . . ?
O9 La1 O1 103.84(6) . . ?
O9 La1 O4 78.86(6) . . ?
O9 La1 O7 127.35(6) . . ?
O9 La1 N3 142.95(6) . 4_565 ?
O9 La1 N1 143.40(6) . . ?
O8 La1 O2 145.85(6) . . ?
O8 La1 O5 68.25(6) . . ?
O8 La1 O9 74.57(6) . . ?
O8 La1 O10 72.00(6) . . ?
O8 La1 O1 136.89(6) . . ?
O8 La1 O4 115.51(6) . . ?
O8 La1 O7 72.26(6) . . ?
O8 La1 N3 137.94(7) . 4_565 ?
O8 La1 N1 82.34(6) . . ?
O10 La1 O2 91.34(6) . . ?
O10 La1 O5 128.66(6) . . ?
O10 La1 O1 66.69(6) . . ?
O10 La1 O7 130.10(6) . . ?
O10 La1 N3 126.30(7) . 4_565 ?
O10 La1 N1 72.91(6) . . ?
O1 La1 O5 151.66(6) . . ?
O1 La1 N3 66.22(7) . 4_565 ?
O4 La1 O2 64.70(6) . . ?
O4 La1 O5 47.27(6) . . ?
O4 La1 O10 147.79(6) . . ?
O4 La1 O1 106.02(6) . . ?
O4 La1 O7 80.01(7) . . ?
O4 La1 N3 70.81(7) . 4_565 ?
O4 La1 N1 137.42(7) . . ?
O7 La1 O2 136.11(6) . . ?
O7 La1 O5 64.17(6) . . ?
O7 La1 O1 128.26(6) . . ?
O7 La1 N3 68.06(7) . 4_565 ?
O7 La1 N1 68.82(7) . . ?
N3 La1 O5 105.01(7) 4_565 . ?
N1 La1 O5 129.99(6) . . ?
N1 La1 O1 74.49(6) . . ?
N1 La1 N3 70.99(7) . 4_565 ?
N5 O2 La1 99.21(14) . . ?
N6 O5 La1 92.43(14) . . ?
La1 O9 H9A 111.2 . . ?
La1 O9 H9B 110.9 . . ?
H9A O9 H9B 107.7 . . ?
La1 O8 H8A 109.6 . . ?
La1 O8 H8B 109.5 . . ?
H8A O8 H8B 109.3 . . ?
La1 O10 H10A 109.4 . . ?
La1 O10 H10B 109.4 . . ?
H10A O10 H10B 109.5 . . ?
N5 O1 La1 96.02(14) . . ?
N6 O4 La1 103.47(14) . . ?
La1 O7 H7A 125.3 . . ?
La1 O7 H7B 125.4 . . ?
H7A O7 H7B 109.4 . . ?
O5 N6 O4 116.8(2) . . ?
O6 N6 O5 122.9(2) . . ?
O6 N6 O4 120.3(2) . . ?
O1 N5 O2 115.7(2) . . ?
O3 N5 O2 121.4(2) . . ?
O3 N5 O1 122.9(2) . . ?
C3 N3 La1 172.3(2) . 4_566 ?
C1 N1 La1 168.2(2) . . ?
N3 C3 B1 175.0(3) . . ?
N1 C1 B1 175.1(3) . . ?
N2 C2 B1 175.3(3) . . ?
N4 C4 B1 177.2(3) . . ?
C1 B1 C3 112.2(2) . . ?
C1 B1 C2 109.7(2) . . ?
C1 B1 C4 106.7(2) . . ?
C2 B1 C3 107.0(2) . . ?
C4 B1 C3 109.0(2) . . ?
C4 B1 C2 112.3(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_EMIM_La_NO3_B_CN4_H2O3
_database_code_depnum_ccdc_archive 'CCDC 1532973'
_audit_update_record             
;
2017-02-15 deposited with the CCDC.
2017-04-20 downloaded from the CCDC.
;
_audit_creation_date             2017-01-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H6 B3 La N13 O6, C6 H11 N2'
_chemical_formula_sum            'C18 H17 B3 La N15 O6'
_chemical_formula_weight         710.80
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
La La -0.2871 2.4523 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.5610(19)
_cell_length_b                   20.688(4)
_cell_length_c                   16.487(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.85(3)
_cell_angle_gamma                90
_cell_volume                     3152.2(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4059
_cell_measurement_temperature    100
_cell_measurement_theta_max      56.478
_cell_measurement_theta_min      4.691
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.412
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6821
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0685 before and 0.0513 after correction.
The Ratio of minimum to maximum transmission is 0.9147.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.056
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            48007
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.326
_diffrn_reflns_theta_min         1.613
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6648
_reflns_number_total             7852
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.649
_refine_diff_density_min         -1.134
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     414
_refine_ls_number_reflns         7852
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.211
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0306P)²+5.6225P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0746
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C15-C16
 2.5 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
3.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C17(H17), C14(H14)
3.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
La1 La 0.72249(2) 0.35408(2) 0.82625(2) 0.00873(5) Uani 1 1 d . . . . .
O4 O 0.6085(2) 0.24864(10) 0.84696(14) 0.0204(4) Uani 1 1 d . . . . .
O5 O 0.6573(2) 0.35186(11) 0.96526(13) 0.0193(4) Uani 1 1 d . . . . .
O6 O 0.6711(2) 0.44173(11) 0.71515(13) 0.0186(4) Uani 1 1 d . . . . .
O1 O 0.7669(2) 0.29653(11) 0.69396(13) 0.0246(5) Uani 1 1 d . . . . .
O2 O 0.5417(2) 0.31239(11) 0.68487(13) 0.0263(5) Uani 1 1 d . . . . .
N8 N 1.0506(2) 0.62463(11) 1.03686(14) 0.0165(5) Uani 1 1 d . . . . .
O3 O 0.6039(3) 0.26058(11) 0.58503(13) 0.0347(6) Uani 1 1 d . . . . .
N4 N -0.0292(2) 0.39463(12) 0.79218(15) 0.0193(5) Uani 1 1 d . . . . .
N2 N 0.4467(2) 0.39606(12) 0.80431(15) 0.0194(5) Uani 1 1 d . . . . .
N6 N 0.7469(2) 0.47639(11) 0.88536(14) 0.0156(5) Uani 1 1 d . . . . .
N10 N 0.9125(2) 0.25551(11) 0.86629(15) 0.0188(5) Uani 1 1 d . . . . .
N9 N 0.8467(3) 0.65267(12) 0.76468(16) 0.0244(5) Uani 1 1 d . . . . .
N1 N 0.6363(3) 0.28903(12) 0.65262(15) 0.0230(5) Uani 1 1 d . . . . .
N7 N 0.5855(3) 0.66245(13) 0.96336(18) 0.0282(6) Uani 1 1 d . . . . .
N13 N 0.9897(3) 0.06061(13) 0.77443(17) 0.0268(6) Uani 1 1 d . . . . .
C7 C 0.9497(3) 0.61608(12) 0.98381(16) 0.0131(5) Uani 1 1 d . . . . .
C11 C 1.2492(3) 0.18131(14) 0.88493(18) 0.0184(6) Uani 1 1 d . . . . .
N3 N 0.1350(3) 0.52659(15) 0.62342(18) 0.0328(6) Uani 1 1 d . . . . .
C5 C 0.7716(3) 0.52990(13) 0.89857(16) 0.0134(5) Uani 1 1 d . . . . .
N12 N 1.3532(3) 0.20530(14) 0.87991(19) 0.0306(6) Uani 1 1 d . . . . .
C8 C 0.8271(3) 0.63365(12) 0.82570(17) 0.0150(5) Uani 1 1 d . . . . .
C12 C 1.0374(3) 0.09990(13) 0.82182(17) 0.0163(5) Uani 1 1 d . . . . .
C1 C 0.3428(3) 0.42595(13) 0.79190(17) 0.0155(5) Uani 1 1 d . . . . .
C9 C 0.9884(3) 0.21208(13) 0.87937(17) 0.0156(5) Uani 1 1 d . . . . .
N11 N 1.1275(4) 0.09281(15) 1.04280(17) 0.0390(7) Uani 1 1 d . . . . .
C6 C 0.6759(3) 0.63975(13) 0.93938(18) 0.0168(5) Uani 1 1 d . . . . .
C3 C 0.0671(3) 0.42432(13) 0.78464(16) 0.0153(5) Uani 1 1 d . . . . .
N5 N 0.2371(3) 0.56079(16) 0.89936(19) 0.0381(7) Uani 1 1 d . . . . .
C2 C 0.1635(3) 0.50206(14) 0.68730(19) 0.0198(6) Uani 1 1 d . . . . .
C10 C 1.1161(3) 0.11896(14) 0.98084(18) 0.0212(6) Uani 1 1 d . . . . .
C4 C 0.2225(3) 0.52266(16) 0.84808(19) 0.0234(6) Uani 1 1 d . . . . .
N14 N 0.1696(4) 0.2901(2) 0.6128(2) 0.0631(12) Uani 1 1 d . . . . .
B2 B 0.8053(3) 0.60532(14) 0.91142(18) 0.0130(5) Uani 1 1 d . . . . .
B1 B 0.1992(3) 0.46880(15) 0.77736(19) 0.0141(6) Uani 1 1 d . . . . .
B3 B 1.0988(3) 0.15289(14) 0.89246(18) 0.0135(6) Uani 1 1 d . . . . .
N15 N 0.1610(3) 0.3623(2) 0.5191(2) 0.0696(14) Uani 1 1 d . . . . .
C18 C 0.0435(5) 0.3249(2) 0.6035(2) 0.0521(13) Uani 1 1 d . . . . .
H18 H -0.0277 0.3179 0.6336 0.062 Uiso 1 1 calc R . . . .
C17 C 0.0384(4) 0.3703(2) 0.5449(2) 0.0411(9) Uani 1 1 d . . . . .
H17 H -0.0356 0.4015 0.5256 0.049 Uiso 1 1 calc R . . . .
C14 C 0.2371(5) 0.3140(4) 0.5609(4) 0.098(3) Uani 1 1 d . . . . .
H14 H 0.3273 0.2991 0.5539 0.118 Uiso 1 1 calc R . . . .
C13 C 0.2283(7) 0.2310(4) 0.6694(3) 0.113(3) Uani 1 1 d . . . . .
H13A H 0.2575 0.2448 0.7282 0.169 Uiso 1 1 calc GR . . . .
H13B H 0.3120 0.2129 0.6533 0.169 Uiso 1 1 calc GR . . . .
H13C H 0.1524 0.1981 0.6624 0.169 Uiso 1 1 calc GR . . . .
C15 C 0.1915(6) 0.3876(3) 0.4386(4) 0.0793(17) Uani 1 1 d D . . . .
H15A H 0.2660 0.3617 0.4213 0.095 Uiso 1 1 calc R . . . .
H15B H 0.1029 0.3901 0.3919 0.095 Uiso 1 1 calc R . . . .
C16 C 0.2459(7) 0.4527(3) 0.4704(5) 0.102(2) Uani 1 1 d D . . . .
H16A H 0.3380 0.4481 0.5131 0.153 Uiso 1 1 calc GR . . . .
H16B H 0.1750 0.4737 0.4953 0.153 Uiso 1 1 calc GR . . . .
H16C H 0.2605 0.4790 0.4239 0.153 Uiso 1 1 calc GR . . . .
H5A H 0.583(5) 0.3466(19) 0.976(2) 0.034(11) Uiso 1 1 d . . . . .
H4A H 0.539(4) 0.2414(19) 0.859(2) 0.033(11) Uiso 1 1 d . . . . .
H6A H 0.652(5) 0.432(2) 0.669(3) 0.048(13) Uiso 1 1 d . . . . .
H4B H 0.618(4) 0.218(2) 0.812(3) 0.042(11) Uiso 1 1 d . . . . .
H6B H 0.624(5) 0.472(2) 0.718(3) 0.046(13) Uiso 1 1 d . . . . .
H5B H 0.696(5) 0.380(2) 1.003(3) 0.049(13) Uiso 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
La1 O4 2.500(2) . ?
La1 O5 2.525(2) . ?
La1 O6 2.534(2) . ?
La1 O1 2.613(2) . ?
La1 O2 2.665(2) . ?
La1 N8 2.736(3) 3_767 ?
La1 N4 2.709(2) 1_655 ?
La1 N2 2.711(2) . ?
La1 N6 2.700(2) . ?
La1 N10 2.698(2) . ?
O4 H4A 0.75(4) . ?
O4 H4B 0.88(4) . ?
O5 H5A 0.78(4) . ?
O5 H5B 0.86(5) . ?
O6 H6A 0.76(5) . ?
O6 H6B 0.78(5) . ?
O1 N1 1.269(3) . ?
O2 N1 1.258(3) . ?
N8 La1 2.736(2) 3_767 ?
N8 C7 1.138(3) . ?
O3 N1 1.228(3) . ?
N4 La1 2.709(2) 1_455 ?
N4 C3 1.139(4) . ?
N2 C1 1.144(4) . ?
N6 C5 1.141(3) . ?
N10 C9 1.140(4) . ?
N9 C8 1.140(4) . ?
N7 C6 1.140(4) . ?
N13 C12 1.139(4) . ?
C7 B2 1.592(4) . ?
C11 N12 1.134(4) . ?
C11 B3 1.587(4) . ?
N3 C2 1.137(4) . ?
C5 B2 1.596(4) . ?
C8 B2 1.592(4) . ?
C12 B3 1.598(4) . ?
C1 B1 1.599(4) . ?
C9 B3 1.595(4) . ?
N11 C10 1.136(4) . ?
C6 B2 1.595(4) . ?
C3 B1 1.593(4) . ?
N5 C4 1.138(4) . ?
C2 B1 1.592(4) . ?
C10 B3 1.588(4) . ?
C4 B1 1.587(4) . ?
N14 C18 1.379(6) . ?
N14 C14 1.294(6) . ?
N14 C13 1.553(7) . ?
N15 C17 1.356(5) . ?
N15 C14 1.322(6) . ?
N15 C15 1.523(7) . ?
C18 H18 0.9500 . ?
C18 C17 1.339(6) . ?
C17 H17 0.9500 . ?
C14 H14 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.489(8) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
O4 La1 O5 69.06(7) . . ?
O4 La1 O6 135.42(7) . . ?
O4 La1 O1 83.46(7) . . ?
O4 La1 O2 68.25(7) . . ?
O4 La1 N8 108.01(7) . 3_767 ?
O4 La1 N4 137.24(7) . 1_655 ?
O4 La1 N2 81.64(7) . . ?
O4 La1 N6 140.23(7) . . ?
O4 La1 N10 66.24(7) . . ?
O5 La1 O6 128.45(7) . . ?
O5 La1 O1 151.64(7) . . ?
O5 La1 O2 122.17(7) . . ?
O5 La1 N8 65.31(7) . 3_767 ?
O5 La1 N4 128.83(8) . 1_655 ?
O5 La1 N2 70.67(8) . . ?
O5 La1 N6 73.02(7) . . ?
O5 La1 N10 94.10(7) . . ?
O6 La1 O1 76.44(7) . . ?
O6 La1 O2 68.73(7) . . ?
O6 La1 N8 116.53(7) . 3_767 ?
O6 La1 N4 69.29(7) . 1_655 ?
O6 La1 N2 70.89(7) . . ?
O6 La1 N6 64.73(7) . . ?
O6 La1 N10 135.33(8) . . ?
O1 La1 O2 47.95(7) . . ?
O1 La1 N8 119.85(7) . 3_767 ?
O1 La1 N4 68.27(7) . 1_655 ?
O1 La1 N2 113.26(7) . . ?
O1 La1 N6 135.29(7) . . ?
O1 La1 N10 67.47(7) . . ?
O2 La1 N8 166.73(7) . 3_767 ?
O2 La1 N4 109.00(7) . 1_655 ?
O2 La1 N2 66.17(7) . . ?
O2 La1 N6 126.56(7) . . ?
O2 La1 N10 102.40(7) . . ?
N4 La1 N8 64.48(7) 1_655 3_767 ?
N4 La1 N2 138.35(7) 1_655 . ?
N2 La1 N8 126.67(7) . 3_767 ?
N6 La1 N8 64.81(7) . 3_767 ?
N6 La1 N4 77.60(7) . 1_655 ?
N6 La1 N2 74.87(7) . . ?
N10 La1 N8 65.03(7) . 3_767 ?
N10 La1 N4 73.37(7) . 1_655 ?
N10 La1 N2 147.75(7) . . ?
N10 La1 N6 129.01(7) . . ?
La1 O4 H4A 131(3) . . ?
La1 O4 H4B 115(3) . . ?
H4A O4 H4B 106(4) . . ?
La1 O5 H5A 131(3) . . ?
La1 O5 H5B 119(3) . . ?
H5A O5 H5B 100(4) . . ?
La1 O6 H6A 119(3) . . ?
La1 O6 H6B 123(3) . . ?
H6A O6 H6B 105(4) . . ?
N1 O1 La1 98.99(16) . . ?
N1 O2 La1 96.80(16) . . ?
C7 N8 La1 175.0(2) . 3_767 ?
C3 N4 La1 164.7(2) . 1_455 ?
C1 N2 La1 165.5(2) . . ?
C5 N6 La1 166.5(2) . . ?
C9 N10 La1 176.2(2) . . ?
O2 N1 O1 116.2(2) . . ?
O3 N1 O1 122.0(3) . . ?
O3 N1 O2 121.8(3) . . ?
N8 C7 B2 178.0(3) . . ?
N12 C11 B3 175.8(3) . . ?
N6 C5 B2 176.7(3) . . ?
N9 C8 B2 177.7(3) . . ?
N13 C12 B3 176.2(3) . . ?
N2 C1 B1 178.2(3) . . ?
N10 C9 B3 176.1(3) . . ?
N7 C6 B2 176.2(3) . . ?
N4 C3 B1 176.8(3) . . ?
N3 C2 B1 178.3(3) . . ?
N11 C10 B3 177.8(3) . . ?
N5 C4 B1 178.7(3) . . ?
C18 N14 C13 130.5(4) . . ?
C14 N14 C18 107.3(4) . . ?
C14 N14 C13 122.2(5) . . ?
C7 B2 C5 110.1(2) . . ?
C7 B2 C6 108.0(2) . . ?
C8 B2 C7 109.2(2) . . ?
C8 B2 C5 108.1(2) . . ?
C8 B2 C6 112.3(2) . . ?
C6 B2 C5 109.2(2) . . ?
C3 B1 C1 109.6(2) . . ?
C2 B1 C1 110.5(2) . . ?
C2 B1 C3 109.6(2) . . ?
C4 B1 C1 109.0(2) . . ?
C4 B1 C3 108.3(2) . . ?
C4 B1 C2 109.8(2) . . ?
C11 B3 C12 111.6(2) . . ?
C11 B3 C9 106.6(2) . . ?
C11 B3 C10 110.6(2) . . ?
C9 B3 C12 108.7(2) . . ?
C10 B3 C12 107.3(2) . . ?
C10 B3 C9 111.9(2) . . ?
C17 N15 C15 127.3(4) . . ?
C14 N15 C17 109.5(4) . . ?
C14 N15 C15 120.7(4) . . ?
N14 C18 H18 125.8 . . ?
C17 C18 N14 108.4(3) . . ?
C17 C18 H18 125.8 . . ?
N15 C17 H17 127.3 . . ?
C18 C17 N15 105.4(4) . . ?
C18 C17 H17 127.3 . . ?
N14 C14 N15 109.4(5) . . ?
N14 C14 H14 125.3 . . ?
N15 C14 H14 125.3 . . ?
N14 C13 H13A 109.5 . . ?
N14 C13 H13B 109.5 . . ?
N14 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N15 C15 H15A 112.3 . . ?
N15 C15 H15B 112.3 . . ?
H15A C15 H15B 109.9 . . ?
C16 C15 N15 97.5(5) . . ?
C16 C15 H15A 112.3 . . ?
C16 C15 H15B 112.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
