# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_jcw119
_database_code_depnum_ccdc_archive 'CCDC 2236565'
loop_
_audit_author_name
_audit_author_address
'Joe Ziller'
;University of California, Irvine
United States of America
;
_audit_update_record             
;
2023-01-16 deposited with the CCDC.	2023-03-14 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 H16 Br N3'
_chemical_formula_weight         210.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   6.6133(5)
_cell_length_b                   11.0336(9)
_cell_length_c                   12.9024(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.338(5)
_cell_angle_gamma                90
_cell_volume                     933.76(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    5831
_cell_measurement_theta_min      5.29
_cell_measurement_theta_max      68.39

_exptl_crystal_description       irregular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_method    not_measured
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.083
_exptl_absorpt_coefficient_mu    5.513
_shelx_estimated_absorpt_T_min   0.492
_shelx_estimated_absorpt_T_max   0.658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2187
_exptl_absorpt_correction_T_max  0.4675
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_absorpt_special_details   
; 
Reflections not merged 
15764 Corrected reflections written to file jcw119s.hkl 
Estimated minimum and maximum transmission:  0.2187  0.4675 
The ratio (0.4678) of these values is more reliable than their absolute values 
Additional spherical absorption correction applied with mu*r =  0.6000 
;
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'IuS microsource'
_diffrn_measurement_device_type  'Bruker X8 Prospector APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15280
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.293
_diffrn_reflns_theta_max         68.825
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1723
_reflns_number_gt                1453
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX3 2017.3-0, 2017'
_computing_cell_refinement       'Bruker SAINT 8.38a, 2013'
_computing_data_reduction        'Bruker SAINT 8.38a, 2013'
_computing_structure_solution    'Bruker SHELXTL 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
A colorless crystal of approximate dimensions 0.150 x 0.114 x 0.083 mm 
was mounted in a cryoloop and transferred to a Bruker X8 Prospector 
diffractometer system.  The APEX3 program package was used to determine 
the unit-cell parameters and for data collection (10 sec/frame scan time).  
The raw frame data was processed using SAINT and SADABS to yield the 
reflection data file.  Subsequent calculations were carried out using 
the SHELXTL program package.  The diffraction symmetry was 2/m and the 
systematic absences were consistent with the monoclinic space group 
P21/n that was later determined to be correct.

The structure was solved by direct methods and refined on F2 by full-matrix 
least-squares techniques.  The analytical scattering factors for neutral 
atoms were used throughout the analysis.  Hydrogen atoms were located from 
a difference-Fourier map and refined (x,y,z and Uiso).

Least-squares analysis yielded wR2 = 0.0700 and Goof = 1.033 for 155 
variables refined against 1723 data (0.83 Å), R1 = 0.0290 for those 
1453 data with I > 2.0sigma(I).  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0344P)²+0.9564P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1723
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0700
_refine_ls_wR_factor_gt          0.0657
_refine_ls_goodness_of_fit_ref   1.033
_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
Br1 Br 0.20102(4) 0.29167(3) 0.95771(2) 0.01869(12) Uani 1 1 d . . . . .
N1 N 0.2634(4) 0.5123(2) 0.80377(19) 0.0201(6) Uani 1 1 d . . . . .
N2 N 0.6021(4) 0.4784(3) 0.7497(2) 0.0244(6) Uani 1 1 d . . . . .
N3 N 0.2968(4) 0.4065(2) 0.64561(19) 0.0169(5) Uani 1 1 d . . . . .
C1 C 0.4811(5) 0.5576(3) 0.8044(3) 0.0276(7) Uani 1 1 d . . . . .
C2 C 0.5011(5) 0.4587(3) 0.6441(2) 0.0192(6) Uani 1 1 d . . . . .
C3 C 0.1710(5) 0.4914(3) 0.6939(2) 0.0181(6) Uani 1 1 d . . . . .
C4 C 0.1370(7) 0.5988(3) 0.8578(3) 0.0328(9) Uani 1 1 d . . . . .
C5 C 0.6648(6) 0.3660(4) 0.8053(3) 0.0303(8) Uani 1 1 d . . . . .
C6 C 0.2027(5) 0.3799(3) 0.5383(2) 0.0227(7) Uani 1 1 d . . . . .
H1 H 0.268(5) 0.439(3) 0.840(3) 0.019(9) Uiso 1 1 d . . . . .
H1A H 0.472(6) 0.637(4) 0.772(3) 0.036(10) Uiso 1 1 d . . . . .
H1B H 0.544(6) 0.559(4) 0.880(3) 0.047(12) Uiso 1 1 d . . . . .
H2A H 0.581(5) 0.402(3) 0.611(3) 0.024(9) Uiso 1 1 d . . . . .
H2B H 0.493(5) 0.537(3) 0.606(2) 0.018(8) Uiso 1 1 d . . . . .
H3A H 0.041(5) 0.463(3) 0.696(2) 0.018(8) Uiso 1 1 d . . . . .
H3B H 0.159(5) 0.572(3) 0.660(3) 0.018(8) Uiso 1 1 d . . . . .
H4A H 0.144(6) 0.682(4) 0.824(3) 0.037(11) Uiso 1 1 d . . . . .
H4B H 0.206(6) 0.602(4) 0.932(3) 0.036(11) Uiso 1 1 d . . . . .
H4C H -0.001(7) 0.570(4) 0.854(3) 0.042(12) Uiso 1 1 d . . . . .
H5A H 0.747(6) 0.317(3) 0.762(3) 0.033(10) Uiso 1 1 d . . . . .
H5B H 0.545(6) 0.315(3) 0.823(3) 0.033(10) Uiso 1 1 d . . . . .
H5C H 0.737(6) 0.385(4) 0.864(3) 0.035(11) Uiso 1 1 d . . . . .
H6A H 0.296(6) 0.321(4) 0.505(3) 0.043(11) Uiso 1 1 d . . . . .
H6B H 0.186(5) 0.457(3) 0.493(3) 0.022(9) Uiso 1 1 d . . . . .
H6C H 0.080(6) 0.344(4) 0.542(3) 0.036(10) 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
N1 C3 1.489(4) . ?
N1 C4 1.498(4) . ?
N1 C1 1.523(4) . ?
N1 H1 0.93(3) . ?
N2 C1 1.430(4) . ?
N2 C2 1.455(4) . ?
N2 C5 1.467(5) . ?
N3 C3 1.446(4) . ?
N3 C2 1.471(4) . ?
N3 C6 1.474(4) . ?
C1 H1A 0.97(4) . ?
C1 H1B 1.00(4) . ?
C2 H2A 0.95(3) . ?
C2 H2B 0.99(3) . ?
C3 H3A 0.92(4) . ?
C3 H3B 0.99(3) . ?
C4 H4A 1.02(4) . ?
C4 H4B 1.01(4) . ?
C4 H4C 0.96(4) . ?
C5 H5A 0.99(4) . ?
C5 H5B 1.02(4) . ?
C5 H5C 0.87(4) . ?
C6 H6A 1.02(4) . ?
C6 H6B 1.03(4) . ?
C6 H6C 0.91(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
C3 N1 C4 110.9(3) . . ?
C3 N1 C1 109.2(2) . . ?
C4 N1 C1 111.9(3) . . ?
C3 N1 H1 109(2) . . ?
C4 N1 H1 108(2) . . ?
C1 N1 H1 108(2) . . ?
C1 N2 C2 109.5(3) . . ?
C1 N2 C5 114.6(3) . . ?
C2 N2 C5 113.5(3) . . ?
C3 N3 C2 109.4(2) . . ?
C3 N3 C6 109.7(2) . . ?
C2 N3 C6 110.1(2) . . ?
N2 C1 N1 112.7(3) . . ?
N2 C1 H1A 110(2) . . ?
N1 C1 H1A 107(2) . . ?
N2 C1 H1B 107(2) . . ?
N1 C1 H1B 107(2) . . ?
H1A C1 H1B 113(3) . . ?
N2 C2 N3 111.0(2) . . ?
N2 C2 H2A 108(2) . . ?
N3 C2 H2A 108(2) . . ?
N2 C2 H2B 109.2(19) . . ?
N3 C2 H2B 110.7(19) . . ?
H2A C2 H2B 110(3) . . ?
N3 C3 N1 108.8(2) . . ?
N3 C3 H3A 113(2) . . ?
N1 C3 H3A 107(2) . . ?
N3 C3 H3B 114.4(19) . . ?
N1 C3 H3B 106.0(19) . . ?
H3A C3 H3B 107(3) . . ?
N1 C4 H4A 108(2) . . ?
N1 C4 H4B 105(2) . . ?
H4A C4 H4B 110(3) . . ?
N1 C4 H4C 111(2) . . ?
H4A C4 H4C 111(3) . . ?
H4B C4 H4C 112(3) . . ?
N2 C5 H5A 109(2) . . ?
N2 C5 H5B 113(2) . . ?
H5A C5 H5B 109(3) . . ?
N2 C5 H5C 108(3) . . ?
H5A C5 H5C 110(3) . . ?
H5B C5 H5C 108(3) . . ?
N3 C6 H6A 109(2) . . ?
N3 C6 H6B 111.8(19) . . ?
H6A C6 H6B 108(3) . . ?
N3 C6 H6C 108(2) . . ?
H6A C6 H6C 110(3) . . ?
H6B C6 H6C 111(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 Br1 0.93(3) 2.31(3) 3.202(3) 161(3) .

_refine_diff_density_max         0.613
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.089

####################################################################### 
# 
# 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_jcw116
_database_code_depnum_ccdc_archive 'CCDC 2236566'
loop_
_audit_author_name
_audit_author_address
'Joe Ziller'
;University of California, Irvine
United States of America
;
_audit_update_record             
;
2023-01-16 deposited with the CCDC.	2023-03-14 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            'C9 H21 Cl3 N3 Y'
_chemical_formula_weight         366.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Y Y -2.7962 3.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.6519(18)
_cell_length_b                   7.6180(11)
_cell_length_c                   15.904(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.870(3)
_cell_angle_gamma                90
_cell_volume                     1532.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    7804
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      30.23

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_method    not_measured
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.177
_exptl_absorpt_coefficient_mu    4.309
_shelx_estimated_absorpt_T_min   0.430
_shelx_estimated_absorpt_T_max   0.516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3449
_exptl_absorpt_correction_T_max  0.4330
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_absorpt_special_details   
; 
Reflections not merged 
24070 Corrected reflections written to file jcw116s.hkl 
Estimated minimum and maximum transmission:  0.3449  0.4330 
The ratio (0.7965) of these values is more reliable than their absolute values 
Additional spherical absorption correction applied with mu*r =  0.6000 
Lambda/2 correction factor = 0.00150 
;
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19925
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.280
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3137
_reflns_number_gt                2475
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2 2014.11-0, 2014'
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_structure_solution    'Bruker SHELXTL 2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
A colorless crystal of approximate dimensions 0.177 x 0.208 x 0.236 mm 
was mounted in a cryoloop and transferred to a Bruker SMART APEX II 
diffractometer system.  The APEX2 program package was used to determine 
the unit-cell parameters and for data collection (30 sec/frame scan time).  
The raw frame data was processed using SAINT and SADABS to yield the 
reflection data file.  Subsequent calculations were carried out using 
the SHELXTL program package.  The diffraction symmetry was 2/m and the 
systematic absences were consistent with the monoclinic space group P21/c 
that was later determined to be correct.

The structure was solved by direct methods and refined on F2 by full-matrix 
least-squares techniques.  The analytical scattering factors5 for neutral 
atoms were used throughout the analysis. Hydrogen atoms were included using 
a riding model.

Least-squares analysis yielded wR2 = 0.1458 and Goof = 1.098 for 149 
variables refined against 3137 data (0.80 Å), R1 = 0.0521 for those 
2475 data with I > 2.0sigma(I). The structure was refined as a 
two-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²+10.2089P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3137
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1458
_refine_ls_wR_factor_gt          0.1279
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.001
_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
Y1 Y 0.24454(5) 0.50395(8) 0.63860(4) 0.01464(18) Uani 1 1 d . . . . .
Cl1 Cl 0.38617(13) 0.2909(2) 0.58820(12) 0.0250(4) Uani 1 1 d . . . . .
Cl2 Cl 0.25757(15) 0.4615(2) 0.79815(10) 0.0271(4) Uani 1 1 d . . . . .
Cl3 Cl 0.07551(13) 0.3346(2) 0.60136(11) 0.0225(4) Uani 1 1 d . . . . .
N1 N 0.2455(5) 0.6538(7) 0.4982(3) 0.0191(12) Uani 1 1 d . . . . .
N2 N 0.3771(4) 0.7471(7) 0.6433(4) 0.0168(11) Uani 1 1 d . . . . .
N3 N 0.1478(4) 0.7865(7) 0.6487(3) 0.0181(12) Uani 1 1 d . . . . .
C1 C 0.3580(5) 0.7072(10) 0.4873(4) 0.0234(15) Uani 1 1 d . . . . .
H1A H 0.3642 0.7729 0.4339 0.028 Uiso 1 1 calc R U . . .
H1B H 0.4023 0.6006 0.4832 0.028 Uiso 1 1 calc R U . . .
C2 C 0.3992(5) 0.8195(9) 0.5583(4) 0.0215(15) Uani 1 1 d . . . . .
H2A H 0.4766 0.8331 0.5526 0.026 Uiso 1 1 calc R U . . .
H2B H 0.3671 0.9376 0.5536 0.026 Uiso 1 1 calc R U . . .
C3 C 0.4775(5) 0.6820(10) 0.6846(5) 0.0245(16) Uani 1 1 d . . . . .
H3A H 0.5234 0.7820 0.6982 0.037 Uiso 1 1 calc R U . . .
H3B H 0.5141 0.6028 0.6461 0.037 Uiso 1 1 calc R U . . .
H3C H 0.4605 0.6188 0.7363 0.037 Uiso 1 1 calc R U . . .
C4 C 0.3279(5) 0.8782(9) 0.7002(4) 0.0213(15) Uani 1 1 d . . . . .
H4A H 0.3747 0.9821 0.7048 0.026 Uiso 1 1 calc R U . . .
H4B H 0.3218 0.8264 0.7570 0.026 Uiso 1 1 calc R U . . .
C5 C 0.2199(5) 0.9366(9) 0.6699(4) 0.0190(14) Uani 1 1 d . . . . .
H5A H 0.1871 1.0089 0.7142 0.023 Uiso 1 1 calc R U . . .
H5B H 0.2279 1.0113 0.6195 0.023 Uiso 1 1 calc R U . . .
C6 C 0.0634(6) 0.7725(9) 0.7124(4) 0.0236(15) Uani 1 1 d . . . . .
H6A H 0.0221 0.8813 0.7129 0.035 Uiso 1 1 calc R U . . .
H6B H 0.0956 0.7534 0.7681 0.035 Uiso 1 1 calc R U . . .
H6C H 0.0169 0.6737 0.6983 0.035 Uiso 1 1 calc R U . . .
C7 C 0.0951(5) 0.8121(9) 0.5640(4) 0.0203(15) Uani 1 1 d . . . . .
H7A H 0.0573 0.9258 0.5635 0.024 Uiso 1 1 calc R U . . .
H7B H 0.0423 0.7179 0.5547 0.024 Uiso 1 1 calc R U . . .
C8 C 0.1736(5) 0.8093(9) 0.4932(4) 0.0216(15) Uani 1 1 d . . . . .
H8A H 0.1347 0.8074 0.4387 0.026 Uiso 1 1 calc R U . . .
H8B H 0.2165 0.9180 0.4954 0.026 Uiso 1 1 calc R U . . .
C9 C 0.2175(6) 0.5251(10) 0.4314(4) 0.0268(17) Uani 1 1 d . . . . .
H9D H 0.2252 0.5801 0.3761 0.040 Uiso 1 1 calc R U . . .
H9A H 0.1441 0.4869 0.4382 0.040 Uiso 1 1 calc R U . . .
H9B H 0.2646 0.4233 0.4357 0.040 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
Y1 N3 2.483(5) . ?
Y1 N2 2.499(5) . ?
Y1 N1 2.508(5) . ?
Y1 Cl1 2.5555(17) . ?
Y1 Cl3 2.5592(18) . ?
Y1 Cl2 2.5610(17) . ?
N1 C9 1.485(9) . ?
N1 C1 1.492(9) . ?
N1 C8 1.495(8) . ?
N2 C2 1.490(9) . ?
N2 C4 1.491(8) . ?
N2 C3 1.505(9) . ?
N3 C6 1.488(8) . ?
N3 C5 1.498(8) . ?
N3 C7 1.506(9) . ?
C1 C2 1.504(10) . ?
C4 C5 1.509(9) . ?
C7 C8 1.513(9) . ?

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
N3 Y1 N2 71.74(18) . . ?
N3 Y1 N1 70.84(17) . . ?
N2 Y1 N1 71.15(19) . . ?
N3 Y1 Cl1 156.86(13) . . ?
N2 Y1 Cl1 90.37(13) . . ?
N1 Y1 Cl1 89.82(13) . . ?
N3 Y1 Cl3 92.35(14) . . ?
N2 Y1 Cl3 159.81(13) . . ?
N1 Y1 Cl3 92.22(14) . . ?
Cl1 Y1 Cl3 101.23(6) . . ?
N3 Y1 Cl2 94.02(13) . . ?
N2 Y1 Cl2 91.78(14) . . ?
N1 Y1 Cl2 159.82(13) . . ?
Cl1 Y1 Cl2 101.28(6) . . ?
Cl3 Y1 Cl2 101.92(6) . . ?
C9 N1 C1 108.4(5) . . ?
C9 N1 C8 110.3(5) . . ?
C1 N1 C8 111.0(5) . . ?
C9 N1 Y1 109.4(4) . . ?
C1 N1 Y1 104.2(4) . . ?
C8 N1 Y1 113.4(4) . . ?
C2 N2 C4 112.8(5) . . ?
C2 N2 C3 110.4(5) . . ?
C4 N2 C3 108.2(5) . . ?
C2 N2 Y1 112.5(4) . . ?
C4 N2 Y1 103.2(4) . . ?
C3 N2 Y1 109.3(4) . . ?
C6 N3 C5 110.0(5) . . ?
C6 N3 C7 107.8(5) . . ?
C5 N3 C7 111.3(5) . . ?
C6 N3 Y1 110.0(4) . . ?
C5 N3 Y1 112.2(4) . . ?
C7 N3 Y1 105.5(4) . . ?
N1 C1 C2 112.9(5) . . ?
N2 C2 C1 113.7(5) . . ?
N2 C4 C5 112.9(5) . . ?
N3 C5 C4 113.1(5) . . ?
N3 C7 C8 112.1(5) . . ?
N1 C8 C7 112.2(5) . . ?

_refine_diff_density_max         1.166
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.140

####################################################################### 
# 
# 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_jcw95
_database_code_depnum_ccdc_archive 'CCDC 2236567'
loop_
_audit_author_name
_audit_author_address
'Joe Ziller'
;University of California, Irvine
United States of America
;
_audit_update_record             
;
2023-01-16 deposited with the CCDC.	2023-03-14 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 H29 I2 N3 O Sm'
_chemical_formula_weight         647.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   17.308(4)
_cell_length_b                   8.404(2)
_cell_length_c                   13.853(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2015.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    5543
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      30.27

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_method    not_measured
_exptl_crystal_density_diffrn    2.135
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.226
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    5.979
_shelx_estimated_absorpt_T_min   0.345
_shelx_estimated_absorpt_T_max   0.534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6191
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_absorpt_special_details   
; 
Reflections not merged 
25736 Corrected reflections written to file jcw95s.hkl 
Estimated minimum and maximum transmission:  0.6191  0.7461 
The ratio (0.8298) of these values is more reliable than their absolute values 
Additional spherical absorption correction applied with mu*r =  0.2000 
Lambda/2 correction factor = 0.00150 
;
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21450
_diffrn_reflns_av_unetI/netI     0.1165
_diffrn_reflns_av_R_equivalents  0.0875
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.353
_diffrn_reflns_theta_max         27.868
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4718
_reflns_number_gt                3222
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.921
_reflns_Friedel_fraction_max     1.000
_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       'Bruker APEX2 2014.11-0, 2014'
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_structure_solution    'Bruker SHELXTL 2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
A green crystal of approximate dimensions 0.226 x 0.166 x 0.120 mm was 
mounted in a cryoloop and transferred to a Bruker SMART APEX II 
diffractometer system.  The APEX2 program package was used to determine 
the unit-cell parameters and for data collection (120 sec/frame scan time).  
The raw frame data was processed using SAINT and SADABS to yield the 
reflection data file.  Subsequent calculations were carried out using the 
SHELXTL program package.  The diffraction symmetry was mmm and the 
systematic absences were consistent with the orthorhombic space groups 
Pnma and Pna21.  It was later determined that space group Pna21 was correct. 

The structure was solved by direct methods and refined on F2 by full-matrix 
least-squares techniques.  The analytical scattering factors for neutral 
atoms were used throughout the analysis.  Hydrogen atoms were included using 
a riding model.  Disordered carbon atoms were included using multiple 
components, partial site-occupancy-factors and equivalent isotropic 
displacement parameters.  

Least-squares analysis yielded wR2 = 0.0563 and Goof = 0.985 for 179 
variables refined against 4718 data (0.76 Å), R1 = 0.0506 for those 3222 
data with I > 2.0sigma(I). The structure was refined as a two-component 
inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0121P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.05(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4718
_refine_ls_number_parameters     179
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.0563
_refine_ls_wR_factor_gt          0.0489
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# start Validation Reply Form
_vrf_PLAT973_jcw95               
;
PROBLEM: Check Calcd Positive Resid. Density on Sm1 1.55 eA-3
RESPONSE: ...Neither disorder nor alternative absorption 
corrections improved the model.
;
# end Validation Reply Form 

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
Sm1 Sm 0.42439(3) 0.62147(6) 0.54744(3) 0.01510(14) Uani 1 1 d . . . . .
I1 I 0.33758(5) 0.37862(10) 0.68862(6) 0.0300(2) Uani 1 1 d . . . . .
I2 I 0.55227(4) 0.79846(10) 0.67235(7) 0.0350(2) Uani 1 1 d . . . . .
O1 O 0.5160(5) 0.4094(9) 0.4851(5) 0.032(2) Uani 1 1 d . . . . .
N1 N 0.3250(5) 0.5782(10) 0.4035(6) 0.018(2) Uani 1 1 d . . . . .
N2 N 0.4369(5) 0.8359(10) 0.4032(6) 0.019(2) Uani 1 1 d . . . . .
N3 N 0.3112(4) 0.8320(9) 0.5460(7) 0.021(2) Uani 1 1 d . . . . .
C1 C 0.3199(7) 0.4053(14) 0.3940(9) 0.033(4) Uani 1 1 d . . . . .
H1A H 0.3702 0.3629 0.3741 0.049 Uiso 1 1 calc R U . . .
H1B H 0.2810 0.3783 0.3453 0.049 Uiso 1 1 calc R U . . .
H1C H 0.3051 0.3587 0.4561 0.049 Uiso 1 1 calc R U . . .
C2 C 0.3664(15) 0.623(3) 0.3114(17) 0.020(7) Uiso 0.5 1 d . . P A 1
H2A H 0.3328 0.6003 0.2552 0.024 Uiso 0.5 1 calc R U P A 1
H2B H 0.4141 0.5590 0.3049 0.024 Uiso 0.5 1 calc R U P A 1
C3 C 0.3869(14) 0.801(3) 0.3134(16) 0.014(6) Uiso 0.5 1 d . . P A 1
H3A H 0.3390 0.8651 0.3157 0.017 Uiso 0.5 1 calc R U P A 1
H3B H 0.4156 0.8296 0.2542 0.017 Uiso 0.5 1 calc R U P A 1
C2B C 0.3417(13) 0.674(3) 0.3153(17) 0.011(6) Uiso 0.5 1 d . . P A 2
H2BA H 0.3049 0.7639 0.3114 0.014 Uiso 0.5 1 calc R U P A 2
H2BB H 0.3343 0.6068 0.2573 0.014 Uiso 0.5 1 calc R U P A 2
C3B C 0.4244(14) 0.739(3) 0.3162(17) 0.020(6) Uiso 0.5 1 d . . P A 2
H3BA H 0.4616 0.6494 0.3153 0.024 Uiso 0.5 1 calc R U P A 2
H3BB H 0.4333 0.8046 0.2580 0.024 Uiso 0.5 1 calc R U P A 2
C4 C 0.5198(7) 0.8708(15) 0.3894(9) 0.037(3) Uani 1 1 d . . . . .
H4A H 0.5474 0.7719 0.3748 0.055 Uiso 1 1 calc R U . . .
H4B H 0.5408 0.9180 0.4484 0.055 Uiso 1 1 calc R U . . .
H4C H 0.5260 0.9455 0.3356 0.055 Uiso 1 1 calc R U . . .
C5 C 0.4022(14) 0.986(3) 0.4514(19) 0.013(7) Uiso 0.5 1 d . . P A 1
H5A H 0.4342 1.0136 0.5082 0.015 Uiso 0.5 1 calc R U P A 1
H5B H 0.4055 1.0753 0.4052 0.015 Uiso 0.5 1 calc R U P A 1
C6 C 0.3186(13) 0.968(3) 0.4839(17) 0.023(6) Uiso 0.5 1 d . . P A 1
H6A H 0.3022 1.0650 0.5189 0.027 Uiso 0.5 1 calc R U P A 1
H6B H 0.2847 0.9550 0.4269 0.027 Uiso 0.5 1 calc R U P A 1
C5B C 0.3927(17) 0.971(3) 0.416(2) 0.027(8) Uiso 0.5 1 d . . P A 2
H5BA H 0.3508 0.9710 0.3672 0.032 Uiso 0.5 1 calc R U P A 2
H5BB H 0.4255 1.0653 0.4038 0.032 Uiso 0.5 1 calc R U P A 2
C6B C 0.3576(14) 0.986(2) 0.5138(14) 0.014(6) Uiso 0.5 1 d . . P A 2
H6BA H 0.3221 1.0782 0.5142 0.017 Uiso 0.5 1 calc R U P A 2
H6BB H 0.3990 1.0067 0.5613 0.017 Uiso 0.5 1 calc R U P A 2
C7 C 0.2949(7) 0.8640(13) 0.6470(7) 0.031(3) Uani 1 1 d . . . . .
H7A H 0.3418 0.9033 0.6787 0.046 Uiso 1 1 calc R U . . .
H7B H 0.2778 0.7658 0.6787 0.046 Uiso 1 1 calc R U . . .
H7C H 0.2541 0.9445 0.6518 0.046 Uiso 1 1 calc R U . . .
C8 C 0.2410(13) 0.727(3) 0.5148(16) 0.023(6) Uiso 0.5 1 d . . P A 1
H8A H 0.2338 0.6408 0.5624 0.028 Uiso 0.5 1 calc R U P A 1
H8B H 0.1937 0.7935 0.5149 0.028 Uiso 0.5 1 calc R U P A 1
C9 C 0.2518(14) 0.654(3) 0.4138(18) 0.018(7) Uiso 0.5 1 d . . P A 1
H9A H 0.2103 0.5749 0.4022 0.021 Uiso 0.5 1 calc R U P A 1
H9B H 0.2468 0.7385 0.3645 0.021 Uiso 0.5 1 calc R U P A 1
C8B C 0.2489(14) 0.805(3) 0.4806(18) 0.024(6) Uiso 0.5 1 d . . P A 2
H8BA H 0.2557 0.8713 0.4222 0.029 Uiso 0.5 1 calc R U P A 2
H8BB H 0.1994 0.8347 0.5115 0.029 Uiso 0.5 1 calc R U P A 2
C9B C 0.2469(15) 0.634(4) 0.453(2) 0.026(7) Uiso 0.5 1 d . . P A 2
H9BA H 0.2035 0.6163 0.4078 0.031 Uiso 0.5 1 calc R U P A 2
H9BB H 0.2375 0.5691 0.5113 0.031 Uiso 0.5 1 calc R U P A 2
C10 C 0.5631(7) 0.4019(17) 0.4036(9) 0.049(4) Uani 1 1 d . . . . .
H10A H 0.5847 0.5085 0.3894 0.059 Uiso 1 1 calc R U . . .
H10B H 0.5325 0.3669 0.3471 0.059 Uiso 1 1 calc R U . . .
C11 C 0.6267(7) 0.2879(15) 0.4217(9) 0.034(3) Uani 1 1 d . . . . .
H11A H 0.6766 0.3292 0.3974 0.041 Uiso 1 1 calc R U . . .
H11B H 0.6160 0.1834 0.3915 0.041 Uiso 1 1 calc R U . . .
C12 C 0.6265(7) 0.2760(17) 0.5311(10) 0.047(4) Uani 1 1 d . . . . .
H12A H 0.6420 0.1678 0.5518 0.056 Uiso 1 1 calc R U . . .
H12B H 0.6631 0.3538 0.5593 0.056 Uiso 1 1 calc R U . . .
C13 C 0.5486(8) 0.3101(16) 0.5620(10) 0.057(4) Uani 1 1 d . . . . .
H13A H 0.5487 0.3680 0.6243 0.068 Uiso 1 1 calc R U . . .
H13B H 0.5186 0.2107 0.5696 0.068 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
Sm1 O1 2.538(7) . ?
Sm1 N3 2.640(7) . ?
Sm1 N1 2.659(8) . ?
Sm1 N2 2.699(8) . ?
Sm1 I2 3.1789(11) . ?
Sm1 I1 3.2012(10) . ?
O1 C10 1.394(13) . ?
O1 C13 1.466(13) . ?
N1 C9 1.43(2) . ?
N1 C1 1.462(13) . ?
N1 C2B 1.49(2) . ?
N1 C2 1.51(2) . ?
N1 C9B 1.59(3) . ?
N2 C5B 1.38(3) . ?
N2 C3B 1.47(2) . ?
N2 C4 1.477(13) . ?
N2 C3 1.54(2) . ?
N2 C5 1.55(3) . ?
N3 C8B 1.43(2) . ?
N3 C6 1.44(2) . ?
N3 C7 1.453(13) . ?
N3 C8 1.56(2) . ?
N3 C6B 1.59(2) . ?
C2 C3 1.54(3) . ?
C2B C3B 1.53(3) . ?
C5 C6 1.52(3) . ?
C5B C6B 1.49(3) . ?
C8 C9 1.54(3) . ?
C8B C9B 1.48(4) . ?
C10 C11 1.480(15) . ?
C11 C12 1.518(18) . ?
C12 C13 1.444(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Sm1 N3 158.8(3) . . ?
O1 Sm1 N1 93.0(3) . . ?
N3 Sm1 N1 66.8(3) . . ?
O1 Sm1 N2 99.6(2) . . ?
N3 Sm1 N2 66.8(3) . . ?
N1 Sm1 N2 65.7(3) . . ?
O1 Sm1 I2 94.52(18) . . ?
N3 Sm1 I2 101.97(19) . . ?
N1 Sm1 I2 157.34(19) . . ?
N2 Sm1 I2 92.00(19) . . ?
O1 Sm1 I1 93.07(18) . . ?
N3 Sm1 I1 94.79(19) . . ?
N1 Sm1 I1 93.86(18) . . ?
N2 Sm1 I1 156.26(19) . . ?
I2 Sm1 I1 107.01(3) . . ?
C10 O1 C13 109.8(9) . . ?
C10 O1 Sm1 132.3(7) . . ?
C13 O1 Sm1 113.1(7) . . ?
C9 N1 C1 113.5(13) . . ?
C1 N1 C2B 118.3(13) . . ?
C9 N1 C2 113.3(16) . . ?
C1 N1 C2 101.5(12) . . ?
C1 N1 C9B 106.5(13) . . ?
C2B N1 C9B 111.0(15) . . ?
C9 N1 Sm1 116.1(11) . . ?
C1 N1 Sm1 104.0(6) . . ?
C2B N1 Sm1 114.5(10) . . ?
C2 N1 Sm1 107.0(10) . . ?
C9B N1 Sm1 100.7(11) . . ?
C5B N2 C3B 118.6(17) . . ?
C5B N2 C4 113.1(14) . . ?
C3B N2 C4 98.4(12) . . ?
C4 N2 C3 118.6(12) . . ?
C4 N2 C5 105.7(11) . . ?
C3 N2 C5 106.6(14) . . ?
C5B N2 Sm1 114.2(12) . . ?
C3B N2 Sm1 103.0(10) . . ?
C4 N2 Sm1 107.8(7) . . ?
C3 N2 Sm1 115.1(9) . . ?
C5 N2 Sm1 101.1(10) . . ?
C8B N3 C7 119.6(13) . . ?
C6 N3 C7 116.5(12) . . ?
C6 N3 C8 110.6(15) . . ?
C7 N3 C8 102.7(11) . . ?
C8B N3 C6B 109.5(15) . . ?
C7 N3 C6B 102.6(10) . . ?
C8B N3 Sm1 117.3(11) . . ?
C6 N3 Sm1 118.2(10) . . ?
C7 N3 Sm1 105.1(6) . . ?
C8 N3 Sm1 101.7(10) . . ?
C6B N3 Sm1 99.9(9) . . ?
N1 C2 C3 109.7(18) . . ?
C2 C3 N2 109.3(17) . . ?
N1 C2B C3B 111.5(18) . . ?
N2 C3B C2B 110.0(18) . . ?
C6 C5 N2 114.6(19) . . ?
N3 C6 C5 109.8(18) . . ?
N2 C5B C6B 114(2) . . ?
C5B C6B N3 113.2(17) . . ?
C9 C8 N3 112.6(16) . . ?
N1 C9 C8 112.2(18) . . ?
N3 C8B C9B 110(2) . . ?
C8B C9B N1 112.3(19) . . ?
O1 C10 C11 109.1(10) . . ?
C10 C11 C12 102.2(10) . . ?
C13 C12 C11 106.5(11) . . ?
C12 C13 O1 104.9(10) . . ?

_refine_diff_density_max         1.252
_refine_diff_density_min         -1.120
_refine_diff_density_rms         0.231

####################################################################### 
# 
# 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_jcw84
_database_code_depnum_ccdc_archive 'CCDC 2236571'
loop_
_audit_author_name
_audit_author_address
'Joe Ziller'
;University of California Irvine
United States of America
;
_audit_update_record             
;
2023-03-10 deposited with the CCDC.	2023-03-14 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         'C12 H30 Cl3 La N6'
_chemical_formula_sum            'C12 H30 Cl3 La N6'
_chemical_formula_weight         503.67

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      hexagonal
_space_group_IT_number           176
_space_group_name_H-M_alt        'P 63/m'
_space_group_name_Hall           '-P 6c'

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

_cell_length_a                   11.9427(7)
_cell_length_b                   11.9427(7)
_cell_length_c                   10.5184(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1299.23(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      30.48

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_method    not_measured
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.381
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.156
_exptl_absorpt_coefficient_mu    1.956
_shelx_estimated_absorpt_T_min   0.523
_shelx_estimated_absorpt_T_max   0.750
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.6149
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_absorpt_special_details   
; 
Reflections not merged 
32254 Corrected reflections written to file jcw84s.hkl 
Estimated minimum and maximum transmission:  0.6149  0.7461 
The ratio (0.8242) of these values is more reliable than their absolute values! 
Additional spherical absorption correction applied with mu*r =  0.2000 
Lambda/2 correction factor = 0.00150 
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31987
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.762
_diffrn_reflns_theta_max         30.502
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             1382
_reflns_number_gt                1329
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 Structure factors included contributions from the .fab file. 
  
 _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       'Bruker APEX2 2014.11-0, 2014'
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_structure_solution    'Bruker SHELXTL 2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
A colorless crystal of approximate dimensions 0.156 x 0.186 x 0.381 mm was mounted in a 
cryoloop and transferred to a Bruker SMART APEX II diffractometer.  The APEX2 program 
package was used to determine the unit-cell parameters and for data collection 
(10 sec/frame scan).  The raw frame data was processed using SAINT and SADABS to 
yield the reflection data file.  Subsequent calculations were carried out using the 
SHELXTL program package.  The systematic absences were consistent with the hexagonal 
space groups P63, P63/m and P6322.  The centrosymmetric space group P63/m was assigned 
and later determined to be correct.

The structure was solved by dual space methods and refined on F2 by full-matrix least-squares
techniques.  The analytical scattering factors for neutral atoms were used throughout 
the analysis. Hydrogen atoms were included using a riding model.

Least-squares analysis yielded wR2 = 0.0317 and Goof = 1.111 for 37 variables refined 
against 1382 data (0.70 Å), R1 = 0.0118 for those 1329 data with I > 2.0sigma(I).

There were several high residuals present in the final difference-Fourier map.  It was 
not possible to determine the nature of the residuals. The crystals were obtained from 
a mixture of THF and hexane, however, a suitable model for the solvent(s) could not be 
established. The SQUEEZE routine in the PLATON program package was used to 
account for the electrons in the solvent accessible voids. The empirical formula reported
does not contain contributions from the unidentified solvent(s).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0135P)²+0.2881P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1382
_refine_ls_number_parameters     37
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0124
_refine_ls_R_factor_gt           0.0118
_refine_ls_wR_factor_ref         0.0317
_refine_ls_wR_factor_gt          0.0315
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_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
La1 La 0.6667 0.3333 0.2500 0.01185(4) Uani 1 6 d S T P . .
Cl1 Cl 0.49327(4) 0.42536(4) 0.2500 0.02610(8) Uani 1 2 d S T P . .
N1 N 0.71313(8) 0.46188(8) 0.48079(8) 0.01754(15) Uani 1 1 d . . . . .
C1 C 0.79824(9) 0.41738(9) 0.53236(9) 0.02020(18) Uani 1 1 d . . . . .
H1A H 0.7950 0.4153 0.6264 0.024 Uiso 1 1 calc R U . . .
H1B H 0.8887 0.4752 0.5051 0.024 Uiso 1 1 calc R U . . .
C2 C 0.76311(11) 0.59957(10) 0.50613(12) 0.0280(2) Uani 1 1 d . . . . .
H2A H 0.7645 0.6136 0.5981 0.042 Uiso 1 1 calc R U . . .
H2B H 0.7072 0.6272 0.4651 0.042 Uiso 1 1 calc R U . . .
H2C H 0.8510 0.6500 0.4722 0.042 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
La1 N1 2.7759(8) 3_665 ?
La1 N1 2.7759(8) 12_666 ?
La1 N1 2.7759(8) 11_656 ?
La1 N1 2.7759(8) 2_655 ?
La1 N1 2.7759(8) . ?
La1 N1 2.7759(8) 10_556 ?
La1 Cl1 2.7878(4) 2_655 ?
La1 Cl1 2.7878(4) 3_665 ?
La1 Cl1 2.7878(4) . ?
N1 C2 1.4663(12) . ?
N1 C1 1.4662(12) . ?
N1 C1 1.4669(12) 2_655 ?
C1 N1 1.4669(12) 3_665 ?

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
N1 La1 N1 121.97(3) 3_665 12_666 ?
N1 La1 N1 151.932(15) 3_665 11_656 ?
N1 La1 N1 49.67(3) 12_666 11_656 ?
N1 La1 N1 49.67(3) 3_665 2_655 ?
N1 La1 N1 151.932(15) 12_666 2_655 ?
N1 La1 N1 121.97(3) 11_656 2_655 ?
N1 La1 N1 49.67(3) 3_665 . ?
N1 La1 N1 151.931(15) 12_666 . ?
N1 La1 N1 151.930(15) 11_656 . ?
N1 La1 N1 49.67(3) 2_655 . ?
N1 La1 N1 151.931(15) 3_665 10_556 ?
N1 La1 N1 49.67(3) 12_666 10_556 ?
N1 La1 N1 49.67(3) 11_656 10_556 ?
N1 La1 N1 151.928(15) 2_655 10_556 ?
N1 La1 N1 121.97(3) . 10_556 ?
N1 La1 Cl1 75.556(17) 3_665 2_655 ?
N1 La1 Cl1 75.556(17) 12_666 2_655 ?
N1 La1 Cl1 76.379(17) 11_656 2_655 ?
N1 La1 Cl1 76.379(17) 2_655 2_655 ?
N1 La1 Cl1 119.009(17) . 2_655 ?
N1 La1 Cl1 119.010(17) 10_556 2_655 ?
N1 La1 Cl1 76.379(17) 3_665 3_665 ?
N1 La1 Cl1 76.379(17) 12_666 3_665 ?
N1 La1 Cl1 119.010(17) 11_656 3_665 ?
N1 La1 Cl1 119.010(17) 2_655 3_665 ?
N1 La1 Cl1 75.555(17) . 3_665 ?
N1 La1 Cl1 75.556(17) 10_556 3_665 ?
Cl1 La1 Cl1 120.0 2_655 3_665 ?
N1 La1 Cl1 119.009(17) 3_665 . ?
N1 La1 Cl1 119.009(17) 12_666 . ?
N1 La1 Cl1 75.554(17) 11_656 . ?
N1 La1 Cl1 75.554(17) 2_655 . ?
N1 La1 Cl1 76.379(17) . . ?
N1 La1 Cl1 76.377(17) 10_556 . ?
Cl1 La1 Cl1 120.0 2_655 . ?
Cl1 La1 Cl1 120.0 3_665 . ?
C2 N1 C1 111.84(8) . . ?
C2 N1 C1 112.02(8) . 2_655 ?
C1 N1 C1 108.95(9) . 2_655 ?
C2 N1 La1 129.49(7) . . ?
C1 N1 La1 96.10(5) . . ?
C1 N1 La1 96.08(5) 2_655 . ?
N1 C1 N1 105.32(8) . 3_665 ?

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.049



####################################################################### 
# 
# 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_jcw115
_database_code_depnum_ccdc_archive 'CCDC 2236568'
loop_
_audit_author_name
_audit_author_address
'Joe Ziller'
;University of California, Irvine
United States of America
;
_audit_update_record             
;
2023-01-16 deposited with the CCDC.	2023-03-14 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            'C29 H54 F12 La N9 O12 S4'
_chemical_formula_weight         1215.96

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.4880(9)
_cell_length_b                   23.4369(19)
_cell_length_c                   19.8069(16)
_cell_angle_alpha                90
_cell_angle_beta                 92.0522(14)
_cell_angle_gamma                90
_cell_volume                     4865.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    9979
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      30.47

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_method    not_measured
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_F_000             2464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.199
_exptl_crystal_size_min          0.176
_exptl_absorpt_coefficient_mu    1.157
_shelx_estimated_absorpt_T_min   0.767
_shelx_estimated_absorpt_T_max   0.822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6267
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_absorpt_special_details   
; 
Reflections not merged 
48623 Corrected reflections written to file jcw115s.hkl 
Estimated minimum and maximum transmission:  0.6267  0.7461 
The ratio (0.8400) of these values is more reliable than their absolute values 
Additional spherical absorption correction applied with mu*r =  0.2000 
Lambda/2 correction factor = 0.00150 
;
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37461
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.738
_diffrn_reflns_theta_max         25.682
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             9139
_reflns_number_gt                6919
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2 2014.11-0, 2014'
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_structure_solution    'Bruker SHELXTL 2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
A colorless crystal of approximate dimensions 0.242 x 0.199 x 0.176 mm 
was mounted in a cryoloop and transferred to a Bruker SMART APEX II 
diffractometer system.  The APEX2 program package was used to determine 
the unit-cell parameters. Data collection used a 120 sec/frame scan time.  
The raw frame data was processed using SAINT and SADABS to yield the 
reflection data file.  Subsequent calculations were carried out using the 
SHELXTL program package.  The diffraction symmetry was 2/m and the 
systematic absences were consistent with the monoclinic space group P21/c 
that was later determined to be correct.

The structure was solved by direct methods and refined on F2 by full-matrix 
least-squares techniques.  The analytical scattering factors for neutral 
atoms were used throughout the analysis.  Hydrogen atom H(7) was located 
from a difference-Fourier map refined (x,y,z and Uiso).  The remaining 
hydrogen atoms were included using a riding model.  There was one molecule 
of toluene present and one molecule of HMe3tach present which is involved 
in hydrogen bonding to triflate oxygen atoms.

Least-squares analysis yielded wR2 = 0.0771 and Goof = 1.009 for 618 variables 
refined against 9139 data (0.82 Å), R1 = 0.0390 for those 6919 data with 
I > 2.0sigma(I).  
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0331P)²+3.0770P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9139
_refine_ls_number_parameters     618
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.0771
_refine_ls_wR_factor_gt          0.0705
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.002
_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
La1 La 0.22479(2) 0.19677(2) 0.57198(2) 0.01251(7) Uani 1 1 d . . . . .
S1 S 0.45139(9) 0.26093(4) 0.70808(5) 0.0224(2) Uani 1 1 d . . . . .
S2 S 0.24108(9) 0.36091(4) 0.59540(5) 0.0241(2) Uani 1 1 d . . . . .
S3 S -0.03776(9) 0.24499(4) 0.43942(5) 0.0283(2) Uani 1 1 d . . . . .
S4 S 0.35894(9) 0.04490(4) 0.63003(5) 0.0246(2) Uani 1 1 d . . . . .
F1 F 0.6604(2) 0.19923(11) 0.71727(11) 0.0430(6) Uani 1 1 d . . . . .
F2 F 0.5955(2) 0.23135(12) 0.81156(12) 0.0534(7) Uani 1 1 d . . . . .
F3 F 0.4989(2) 0.16105(10) 0.76420(13) 0.0485(7) Uani 1 1 d . . . . .
F4 F 0.1713(2) 0.46206(9) 0.55433(12) 0.0443(6) Uani 1 1 d . . . . .
F5 F 0.1579(2) 0.39863(9) 0.47661(12) 0.0388(6) Uani 1 1 d . . . . .
F6 F 0.0187(2) 0.40064(11) 0.55378(14) 0.0552(7) Uani 1 1 d . . . . .
F7 F -0.1779(2) 0.21547(13) 0.33390(13) 0.0671(9) Uani 1 1 d . . . . .
F8 F 0.0091(3) 0.17983(11) 0.33609(13) 0.0555(7) Uani 1 1 d . . . . .
F9 F -0.1318(3) 0.14697(13) 0.40153(15) 0.0911(12) Uani 1 1 d . . . . .
F10 F 0.3344(3) -0.01578(10) 0.51916(13) 0.0557(7) Uani 1 1 d . . . . .
F11 F 0.1700(2) -0.01690(10) 0.58070(15) 0.0571(8) Uani 1 1 d . . . . .
F12 F 0.3375(2) -0.06447(9) 0.61107(13) 0.0438(6) Uani 1 1 d . . . . .
O1 O 0.3936(2) 0.22637(11) 0.65472(12) 0.0244(6) Uani 1 1 d . . . . .
O2 O 0.5375(2) 0.30346(11) 0.68426(13) 0.0340(7) Uani 1 1 d . . . . .
O3 O 0.3639(2) 0.27840(11) 0.75766(12) 0.0307(6) Uani 1 1 d . . . . .
O4 O 0.2035(2) 0.30410(10) 0.57303(11) 0.0208(5) Uani 1 1 d . . . . .
O5 O 0.3689(2) 0.37647(11) 0.57792(13) 0.0295(6) Uani 1 1 d . . . . .
O6 O 0.2066(2) 0.37477(11) 0.66285(13) 0.0343(7) Uani 1 1 d . . . . .
O7 O 0.0534(2) 0.21107(10) 0.48076(11) 0.0209(6) Uani 1 1 d . . . . .
O8 O -0.1521(3) 0.25817(15) 0.47335(15) 0.0552(9) Uani 1 1 d . . . . .
O9 O 0.0192(3) 0.28949(11) 0.40255(14) 0.0415(8) Uani 1 1 d . . . . .
O10 O 0.2945(2) 0.09304(10) 0.59643(11) 0.0200(6) Uani 1 1 d . . . . .
O11 O 0.4933(2) 0.04187(12) 0.62081(15) 0.0423(8) Uani 1 1 d . . . . .
O12 O 0.3176(3) 0.03399(11) 0.69678(13) 0.0410(8) Uani 1 1 d . . . . .
N1 N 0.4740(3) 0.17792(12) 0.52469(14) 0.0187(7) Uani 1 1 d . . . . .
N2 N 0.3475(3) 0.24358(12) 0.46302(14) 0.0197(7) Uani 1 1 d . . . . .
N3 N 0.3058(3) 0.14593(13) 0.45404(14) 0.0206(7) Uani 1 1 d . . . . .
N4 N 0.1378(2) 0.16590(12) 0.70026(13) 0.0156(6) Uani 1 1 d . . . . .
N5 N 0.0086(3) 0.23153(12) 0.63954(15) 0.0204(7) Uani 1 1 d . . . . .
N6 N 0.0106(2) 0.13566(12) 0.60718(14) 0.0169(7) Uani 1 1 d . . . . .
C1 C 0.4769(3) 0.23279(16) 0.48951(18) 0.0235(9) Uani 1 1 d . . . . .
H1A H 0.5044 0.2635 0.5211 0.028 Uiso 1 1 calc R U . . .
H1B H 0.5371 0.2313 0.4522 0.028 Uiso 1 1 calc R U . . .
C2 C 0.3407(4) 0.30017(16) 0.43071(18) 0.0279(9) Uani 1 1 d . . . . .
H2A H 0.2521 0.3085 0.4166 0.042 Uiso 1 1 calc R U . . .
H2B H 0.3941 0.3004 0.3911 0.042 Uiso 1 1 calc R U . . .
H2C H 0.3714 0.3292 0.4629 0.042 Uiso 1 1 calc R U . . .
C3 C 0.3108(3) 0.19884(16) 0.41495(17) 0.0242(9) Uani 1 1 d . . . . .
H3A H 0.3742 0.1957 0.3793 0.029 Uiso 1 1 calc R U . . .
H3B H 0.2263 0.2073 0.3933 0.029 Uiso 1 1 calc R U . . .
C4 C 0.2495(4) 0.09894(17) 0.41378(19) 0.0336(10) Uani 1 1 d . . . . .
H4A H 0.2520 0.0638 0.4406 0.050 Uiso 1 1 calc R U . . .
H4B H 0.2981 0.0935 0.3730 0.050 Uiso 1 1 calc R U . . .
H4C H 0.1608 0.1082 0.4010 0.050 Uiso 1 1 calc R U . . .
C5 C 0.4372(3) 0.13322(16) 0.47659(18) 0.0240(9) Uani 1 1 d . . . . .
H5A H 0.4422 0.0953 0.4985 0.029 Uiso 1 1 calc R U . . .
H5B H 0.4943 0.1334 0.4378 0.029 Uiso 1 1 calc R U . . .
C6 C 0.5991(3) 0.16580(18) 0.55792(19) 0.0304(10) Uani 1 1 d . . . . .
H6A H 0.6242 0.1979 0.5872 0.046 Uiso 1 1 calc R U . . .
H6B H 0.6629 0.1605 0.5235 0.046 Uiso 1 1 calc R U . . .
H6C H 0.5932 0.1310 0.5851 0.046 Uiso 1 1 calc R U . . .
C7 C 0.0596(3) 0.21723(15) 0.70712(18) 0.0206(8) Uani 1 1 d . . . . .
H7A H -0.0108 0.2099 0.7379 0.025 Uiso 1 1 calc R U . . .
H7B H 0.1120 0.2491 0.7257 0.025 Uiso 1 1 calc R U . . .
C8 C -0.0625(4) 0.28582(16) 0.6406(2) 0.0303(10) Uani 1 1 d . . . . .
H8A H -0.0072 0.3159 0.6597 0.045 Uiso 1 1 calc R U . . .
H8B H -0.1373 0.2815 0.6684 0.045 Uiso 1 1 calc R U . . .
H8C H -0.0902 0.2962 0.5945 0.045 Uiso 1 1 calc R U . . .
C9 C -0.0728(3) 0.18513(15) 0.61425(18) 0.0195(8) Uani 1 1 d . . . . .
H9A H -0.1136 0.1954 0.5701 0.023 Uiso 1 1 calc R U . . .
H9B H -0.1405 0.1768 0.6464 0.023 Uiso 1 1 calc R U . . .
C10 C -0.0565(3) 0.08908(16) 0.57164(18) 0.0251(9) Uani 1 1 d . . . . .
H10A H -0.0820 0.1015 0.5259 0.038 Uiso 1 1 calc R U . . .
H10B H -0.1325 0.0786 0.5962 0.038 Uiso 1 1 calc R U . . .
H10C H 0.0002 0.0560 0.5691 0.038 Uiso 1 1 calc R U . . .
C11 C 0.0563(3) 0.11906(15) 0.67537(16) 0.0171(8) Uani 1 1 d . . . . .
H11A H -0.0164 0.1135 0.7052 0.021 Uiso 1 1 calc R U . . .
H11B H 0.1056 0.0831 0.6738 0.021 Uiso 1 1 calc R U . . .
C12 C 0.1990(3) 0.15110(16) 0.76604(16) 0.0228(9) Uani 1 1 d . . . . .
H12A H 0.2552 0.1181 0.7606 0.034 Uiso 1 1 calc R U . . .
H12B H 0.1332 0.1417 0.7982 0.034 Uiso 1 1 calc R U . . .
H12C H 0.2491 0.1836 0.7831 0.034 Uiso 1 1 calc R U . . .
C13 C 0.5559(4) 0.21047(18) 0.7525(2) 0.0321(10) Uani 1 1 d . . . . .
C14 C 0.1418(4) 0.40748(17) 0.5423(2) 0.0306(10) Uani 1 1 d . . . . .
C15 C -0.0876(4) 0.1940(2) 0.3746(2) 0.0438(12) Uani 1 1 d . . . . .
C16 C 0.2963(4) -0.01577(17) 0.5823(2) 0.0345(10) Uani 1 1 d . . . . .
N7 N 0.5143(3) 0.42949(14) 0.68808(16) 0.0238(7) Uani 1 1 d . . . . .
H7 H 0.485(3) 0.4020(15) 0.6583(18) 0.025(10) Uiso 1 1 d . . . . .
N8 N 0.5361(3) 0.49742(13) 0.59846(15) 0.0293(8) Uani 1 1 d . . . . .
N9 N 0.7162(3) 0.43887(15) 0.63027(16) 0.0325(8) Uani 1 1 d . . . . .
C17 C 0.4772(4) 0.48743(16) 0.66239(19) 0.0283(9) Uani 1 1 d . . . . .
H17A H 0.3832 0.4899 0.6564 0.034 Uiso 1 1 calc R U . . .
H17B H 0.5055 0.5169 0.6955 0.034 Uiso 1 1 calc R U . . .
C18 C 0.4936(4) 0.55199(17) 0.5704(2) 0.0420(11) Uani 1 1 d . . . . .
H18A H 0.4004 0.5522 0.5653 0.063 Uiso 1 1 calc R U . . .
H18B H 0.5307 0.5576 0.5262 0.063 Uiso 1 1 calc R U . . .
H18C H 0.5214 0.5829 0.6009 0.063 Uiso 1 1 calc R U . . .
C19 C 0.6748(4) 0.49477(18) 0.6072(2) 0.0367(11) Uani 1 1 d . . . . .
H19A H 0.7140 0.5035 0.5636 0.044 Uiso 1 1 calc R U . . .
H19B H 0.7040 0.5239 0.6404 0.044 Uiso 1 1 calc R U . . .
C20 C 0.7027(3) 0.39446(18) 0.57839(19) 0.0341(10) Uani 1 1 d . . . . .
H20A H 0.6132 0.3919 0.5626 0.051 Uiso 1 1 calc R U . . .
H20B H 0.7300 0.3577 0.5975 0.051 Uiso 1 1 calc R U . . .
H20C H 0.7558 0.4041 0.5403 0.051 Uiso 1 1 calc R U . . .
C21 C 0.6603(3) 0.42520(18) 0.6929(2) 0.0326(10) Uani 1 1 d . . . . .
H21A H 0.6937 0.4516 0.7284 0.039 Uiso 1 1 calc R U . . .
H21B H 0.6852 0.3859 0.7064 0.039 Uiso 1 1 calc R U . . .
C22 C 0.4570(4) 0.41819(17) 0.75422(18) 0.0301(10) Uani 1 1 d . . . . .
H22A H 0.4776 0.4497 0.7853 0.045 Uiso 1 1 calc R U . . .
H22B H 0.4915 0.3825 0.7731 0.045 Uiso 1 1 calc R U . . .
H22C H 0.3642 0.4150 0.7480 0.045 Uiso 1 1 calc R U . . .
C23 C -0.0765(4) -0.00147(18) 0.7677(2) 0.0369(11) Uani 1 1 d . . . . .
C24 C -0.1857(4) 0.01910(18) 0.7330(2) 0.0368(11) Uani 1 1 d . . . . .
H24 H -0.2167 -0.0005 0.6938 0.044 Uiso 1 1 calc R U . . .
C25 C -0.2495(4) 0.06678(19) 0.7540(2) 0.0374(11) Uani 1 1 d . . . . .
H25 H -0.3233 0.0798 0.7294 0.045 Uiso 1 1 calc R U . . .
C26 C -0.2050(4) 0.09600(19) 0.8117(2) 0.0395(11) Uani 1 1 d . . . . .
H26 H -0.2477 0.1292 0.8267 0.047 Uiso 1 1 calc R U . . .
C27 C -0.0986(4) 0.07586(19) 0.8464(2) 0.0379(11) Uani 1 1 d . . . . .
H27 H -0.0682 0.0952 0.8859 0.045 Uiso 1 1 calc R U . . .
C28 C -0.0351(4) 0.02818(18) 0.8250(2) 0.0370(11) Uani 1 1 d . . . . .
H28 H 0.0384 0.0153 0.8500 0.044 Uiso 1 1 calc R U . . .
C29 C -0.0077(4) -0.0526(2) 0.7445(3) 0.0570(14) Uani 1 1 d . . . . .
H29A H 0.0347 -0.0437 0.7025 0.085 Uiso 1 1 calc R U . . .
H29B H -0.0686 -0.0838 0.7365 0.085 Uiso 1 1 calc R U . . .
H29C H 0.0561 -0.0641 0.7792 0.085 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
La1 O1 2.468(2) . ?
La1 O7 2.525(2) . ?
La1 O4 2.525(2) . ?
La1 O10 2.579(2) . ?
La1 N6 2.774(3) . ?
La1 N2 2.778(3) . ?
La1 N3 2.782(3) . ?
La1 N5 2.795(3) . ?
La1 N4 2.824(3) . ?
La1 N1 2.842(3) . ?
S1 O3 1.427(3) . ?
S1 O2 1.436(3) . ?
S1 O1 1.447(2) . ?
S1 C13 1.819(4) . ?
S2 O6 1.434(3) . ?
S2 O5 1.444(2) . ?
S2 O4 1.453(2) . ?
S2 C14 1.818(4) . ?
S3 O9 1.417(3) . ?
S3 O8 1.430(3) . ?
S3 O7 1.470(2) . ?
S3 C15 1.818(5) . ?
S4 O12 1.429(3) . ?
S4 O11 1.429(3) . ?
S4 O10 1.463(2) . ?
S4 C16 1.818(4) . ?
F1 C13 1.347(4) . ?
F2 C13 1.320(4) . ?
F3 C13 1.327(4) . ?
F4 C14 1.336(4) . ?
F5 C14 1.334(4) . ?
F6 C14 1.328(4) . ?
F7 C15 1.322(5) . ?
F8 C15 1.332(5) . ?
F9 C15 1.316(5) . ?
F10 C16 1.326(5) . ?
F11 C16 1.324(4) . ?
F12 C16 1.340(4) . ?
N1 C5 1.459(4) . ?
N1 C1 1.464(4) . ?
N1 C6 1.474(4) . ?
N2 C1 1.459(4) . ?
N2 C3 1.459(4) . ?
N2 C2 1.473(4) . ?
N3 C3 1.464(4) . ?
N3 C5 1.464(4) . ?
N3 C4 1.471(5) . ?
N4 C7 1.465(4) . ?
N4 C11 1.466(4) . ?
N4 C12 1.473(4) . ?
N5 C9 1.461(4) . ?
N5 C7 1.463(4) . ?
N5 C8 1.475(4) . ?
N6 C9 1.462(4) . ?
N6 C10 1.465(4) . ?
N6 C11 1.469(4) . ?
N7 C22 1.484(5) . ?
N7 C17 1.497(5) . ?
N7 C21 1.535(5) . ?
N8 C17 1.447(5) . ?
N8 C18 1.457(5) . ?
N8 C19 1.460(5) . ?
N9 C21 1.428(5) . ?
N9 C19 1.449(5) . ?
N9 C20 1.466(5) . ?
C23 C28 1.388(6) . ?
C23 C24 1.400(6) . ?
C23 C29 1.479(6) . ?
C24 C25 1.374(6) . ?
C25 C26 1.399(6) . ?
C26 C27 1.373(6) . ?
C27 C28 1.375(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 La1 O7 155.93(8) . . ?
O1 La1 O4 77.06(8) . . ?
O7 La1 O4 79.21(7) . . ?
O1 La1 O10 87.05(8) . . ?
O7 La1 O10 116.69(7) . . ?
O4 La1 O10 164.10(7) . . ?
O1 La1 N6 123.11(8) . . ?
O7 La1 N6 71.71(8) . . ?
O4 La1 N6 116.07(7) . . ?
O10 La1 N6 72.12(7) . . ?
O1 La1 N2 93.64(8) . . ?
O7 La1 N2 74.30(8) . . ?
O4 La1 N2 69.91(8) . . ?
O10 La1 N2 112.45(8) . . ?
N6 La1 N2 143.23(8) . . ?
O1 La1 N3 116.38(8) . . ?
O7 La1 N3 71.76(8) . . ?
O4 La1 N3 117.59(8) . . ?
O10 La1 N3 70.18(8) . . ?
N6 La1 N3 105.33(8) . . ?
N2 La1 N3 49.67(8) . . ?
O1 La1 N5 100.09(8) . . ?
O7 La1 N5 74.64(8) . . ?
O4 La1 N5 68.43(8) . . ?
O10 La1 N5 114.46(8) . . ?
N6 La1 N5 49.61(8) . . ?
N2 La1 N5 131.55(8) . . ?
N3 La1 N5 143.54(8) . . ?
O1 La1 N4 73.85(8) . . ?
O7 La1 N4 115.68(7) . . ?
O4 La1 N4 102.49(7) . . ?
O10 La1 N4 71.83(7) . . ?
N6 La1 N4 49.55(8) . . ?
N2 La1 N4 166.80(8) . . ?
N3 La1 N4 139.80(8) . . ?
N5 La1 N4 49.49(8) . . ?
O1 La1 N1 67.44(8) . . ?
O7 La1 N1 115.10(8) . . ?
O4 La1 N1 103.89(8) . . ?
O10 La1 N1 69.98(8) . . ?
N6 La1 N1 139.91(8) . . ?
N2 La1 N1 49.32(8) . . ?
N3 La1 N1 49.04(8) . . ?
N5 La1 N1 166.99(8) . . ?
N4 La1 N1 125.94(8) . . ?
O3 S1 O2 117.01(16) . . ?
O3 S1 O1 113.60(15) . . ?
O2 S1 O1 113.60(15) . . ?
O3 S1 C13 104.14(17) . . ?
O2 S1 C13 103.60(17) . . ?
O1 S1 C13 102.66(17) . . ?
O6 S2 O5 115.72(16) . . ?
O6 S2 O4 114.63(15) . . ?
O5 S2 O4 113.72(15) . . ?
O6 S2 C14 104.16(18) . . ?
O5 S2 C14 103.14(16) . . ?
O4 S2 C14 103.31(16) . . ?
O9 S3 O8 117.35(19) . . ?
O9 S3 O7 114.02(15) . . ?
O8 S3 O7 113.27(16) . . ?
O9 S3 C15 103.62(19) . . ?
O8 S3 C15 104.5(2) . . ?
O7 S3 C15 101.70(17) . . ?
O12 S4 O11 116.27(17) . . ?
O12 S4 O10 114.10(15) . . ?
O11 S4 O10 114.94(15) . . ?
O12 S4 C16 103.01(19) . . ?
O11 S4 C16 103.55(18) . . ?
O10 S4 C16 102.37(17) . . ?
S1 O1 La1 156.03(15) . . ?
S2 O4 La1 153.13(14) . . ?
S3 O7 La1 154.51(14) . . ?
S4 O10 La1 159.30(14) . . ?
C5 N1 C1 109.2(3) . . ?
C5 N1 C6 111.3(3) . . ?
C1 N1 C6 110.4(3) . . ?
C5 N1 La1 95.88(18) . . ?
C1 N1 La1 93.16(18) . . ?
C6 N1 La1 134.2(2) . . ?
C1 N2 C3 109.3(3) . . ?
C1 N2 C2 110.0(3) . . ?
C3 N2 C2 110.9(3) . . ?
C1 N2 La1 95.91(19) . . ?
C3 N2 La1 95.98(19) . . ?
C2 N2 La1 132.6(2) . . ?
C3 N3 C5 106.5(3) . . ?
C3 N3 C4 111.6(3) . . ?
C5 N3 C4 111.6(3) . . ?
C3 N3 La1 95.68(19) . . ?
C5 N3 La1 98.26(19) . . ?
C4 N3 La1 130.3(2) . . ?
C7 N4 C11 108.9(3) . . ?
C7 N4 C12 109.8(3) . . ?
C11 N4 C12 110.6(3) . . ?
C7 N4 La1 94.19(18) . . ?
C11 N4 La1 95.30(18) . . ?
C12 N4 La1 135.4(2) . . ?
C9 N5 C7 109.5(3) . . ?
C9 N5 C8 110.9(3) . . ?
C7 N5 C8 110.7(3) . . ?
C9 N5 La1 95.36(18) . . ?
C7 N5 La1 95.46(18) . . ?
C8 N5 La1 132.6(2) . . ?
C9 N6 C10 111.0(3) . . ?
C9 N6 C11 107.4(3) . . ?
C10 N6 C11 112.3(3) . . ?
C9 N6 La1 96.18(18) . . ?
C10 N6 La1 130.0(2) . . ?
C11 N6 La1 97.29(18) . . ?
N2 C1 N1 106.8(3) . . ?
N2 C3 N3 106.1(3) . . ?
N1 C5 N3 106.1(3) . . ?
N5 C7 N4 106.9(3) . . ?
N5 C9 N6 106.2(3) . . ?
N4 C11 N6 106.2(3) . . ?
F2 C13 F3 107.4(3) . . ?
F2 C13 F1 107.2(3) . . ?
F3 C13 F1 107.4(3) . . ?
F2 C13 S1 110.6(3) . . ?
F3 C13 S1 112.6(3) . . ?
F1 C13 S1 111.3(3) . . ?
F6 C14 F5 107.8(3) . . ?
F6 C14 F4 107.8(3) . . ?
F5 C14 F4 106.7(3) . . ?
F6 C14 S2 111.6(3) . . ?
F5 C14 S2 112.4(3) . . ?
F4 C14 S2 110.3(3) . . ?
F9 C15 F7 108.1(4) . . ?
F9 C15 F8 108.1(4) . . ?
F7 C15 F8 106.9(4) . . ?
F9 C15 S3 111.1(3) . . ?
F7 C15 S3 111.2(4) . . ?
F8 C15 S3 111.3(3) . . ?
F11 C16 F10 108.2(4) . . ?
F11 C16 F12 107.5(3) . . ?
F10 C16 F12 107.3(3) . . ?
F11 C16 S4 111.8(3) . . ?
F10 C16 S4 112.0(3) . . ?
F12 C16 S4 109.9(3) . . ?
C22 N7 C17 110.7(3) . . ?
C22 N7 C21 111.5(3) . . ?
C17 N7 C21 109.1(3) . . ?
C17 N8 C18 110.0(3) . . ?
C17 N8 C19 110.1(3) . . ?
C18 N8 C19 111.8(3) . . ?
C21 N9 C19 110.5(3) . . ?
C21 N9 C20 114.7(3) . . ?
C19 N9 C20 113.6(3) . . ?
N8 C17 N7 109.3(3) . . ?
N9 C19 N8 111.2(3) . . ?
N9 C21 N7 111.7(3) . . ?
C28 C23 C24 117.1(4) . . ?
C28 C23 C29 121.2(4) . . ?
C24 C23 C29 121.7(4) . . ?
C25 C24 C23 122.1(4) . . ?
C24 C25 C26 119.5(4) . . ?
C27 C26 C25 118.8(4) . . ?
C26 C27 C28 121.3(4) . . ?
C27 C28 C23 121.2(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N7 H7 O2 0.92(4) 2.43(4) 2.965(4) 118(3) .
N7 H7 O5 0.92(4) 2.06(4) 2.897(4) 151(3) .

_refine_diff_density_max         0.640
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.099

####################################################################### 
# 
# 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_jcw114
_database_code_depnum_ccdc_archive 'CCDC 2236570'
loop_
_audit_author_name
_audit_author_address
'Justin Wedal'
;University of California Irvine
United States of America
;
_audit_update_record             
;
2023-01-16 deposited with the CCDC.	2023-03-14 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 H29 I3 La N3 O'
_chemical_formula_weight         763.00

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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   16.0712(13)
_cell_length_b                   10.0909(8)
_cell_length_c                   13.2624(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2150.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    9938
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      30.40

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_method    not_measured
_exptl_crystal_density_diffrn    2.356
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.184
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.082
_exptl_absorpt_coefficient_mu    6.295
_shelx_estimated_absorpt_T_min   0.390
_shelx_estimated_absorpt_T_max   0.626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3064
_exptl_absorpt_correction_T_max  0.4330
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_absorpt_special_details   
; 
Reflections not merged 
27344 Corrected reflections written to file jcw114s.hkl 
Estimated minimum and maximum transmission:  0.3064  0.4330 
The ratio (0.7076) of these values is more reliable than their absolute values! 
Additional spherical absorption correction applied with mu*r =  0.6000 
Lambda/2 correction factor = 0.00150 
;
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25962
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.383
_diffrn_reflns_theta_max         30.510
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6364
_reflns_number_gt                5660
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.926
_reflns_Friedel_fraction_max     0.997
_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       'Bruker APEX2 2014.11-0, 2014'
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_structure_solution    'Bruker SHELXTL 2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
A colorless crystal of approximate dimensions 0.184 x 0.165 x 0.082 mm was 
mounted in a cryoloop and transferred to a Bruker SMART APEX II diffractometer 
system.  The APEX2 program package was used to determine the unit-cell 
parameters and for data collection (90 sec/frame scan time).  The raw frame 
data was processed using SAINT and SADABS to yield the reflection data file.  
Subsequent calculations were carried out using the SHELXTL program package.  
The diffraction symmetry was mmm and the systematic absences were consistent 
with the orthorhombic space groups Pnma and Pna21.  It was later determined 
that space group Pna21 was correct. 

The structure was solved by direct methods and refined on F2 by full-matrix 
least-squares techniques.  The analytical scattering factors for neutral 
atoms were used throughout the analysis.  Hydrogen atoms were included using 
a riding model.  The structure was refined as an inversion twin.

Least-squares analysis yielded wR2 = 0.0873 and Goof = 1.021 for 193 variables 
refined against 6364 data (0.70 Å), R1 = 0.0397 for those 5660 data with 
I > 2.0sigma(I).
 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+8.2419P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as a perfect inversion twin. 
;
_refine_ls_abs_structure_Flack   0.5
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6364
_refine_ls_number_parameters     193
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0872
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

# start Validation Reply Form
_vrf_PLAT971_jcw114              
;
PROBLEM: Check Calcd Resid. Dens.  0.85Ang From I1              3.86 eA-3  
RESPONSE: ...Residual density was observed near the I atom.  Neither  
disorder nor alternative absorption corrections improved the model.
;
_vrf_PLAT987_jcw114              
;
PROBLEM: The Flack x is >> 0 -  Do a BASF/TWIN Refinement     Please Check 
RESPONSE: ...Structure was refined as an inversion twin.
;
# end Validation Reply Form

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 0.29596(3) 0.60288(5) 0.50683(5) 0.00858(10) Uani 1 1 d . . . . .
I1 I 0.22543(4) 0.31423(6) 0.54889(7) 0.02458(17) Uani 1 1 d . . . . .
I2 I 0.40994(4) 0.67750(7) 0.31984(5) 0.02101(16) Uani 1 1 d . . . . .
I3 I 0.38556(4) 0.69308(6) 0.70515(5) 0.01726(14) Uani 1 1 d . . . . .
O1 O 0.4209(4) 0.4350(6) 0.5032(6) 0.0162(13) Uani 1 1 d . . . . .
N1 N 0.1508(6) 0.6734(9) 0.6030(7) 0.0176(18) Uani 1 1 d . . . . .
N2 N 0.1673(6) 0.6406(9) 0.3830(7) 0.0167(18) Uani 1 1 d . . . . .
N3 N 0.2490(5) 0.8624(8) 0.4830(6) 0.0160(18) Uani 1 1 d . . . . .
C1 C 0.0769(6) 0.6595(11) 0.5357(8) 0.019(2) Uani 1 1 d . . . . .
H1A H 0.0333 0.6094 0.5722 0.023 Uiso 1 1 calc R U . . .
H1B H 0.0545 0.7490 0.5215 0.023 Uiso 1 1 calc R U . . .
C2 C 0.0933(7) 0.5917(11) 0.4377(8) 0.019(2) Uani 1 1 d . . . . .
H2A H 0.1004 0.4957 0.4506 0.023 Uiso 1 1 calc R U . . .
H2B H 0.0440 0.6026 0.3938 0.023 Uiso 1 1 calc R U . . .
C3 C 0.1834(7) 0.5511(12) 0.2960(8) 0.024(2) Uani 1 1 d . . . . .
H3A H 0.2212 0.5948 0.2485 0.036 Uiso 1 1 calc R U . . .
H3B H 0.1308 0.5308 0.2620 0.036 Uiso 1 1 calc R U . . .
H3C H 0.2088 0.4687 0.3202 0.036 Uiso 1 1 calc R U . . .
C4 C 0.1544(7) 0.7807(11) 0.3466(9) 0.023(2) Uani 1 1 d . . . . .
H4A H 0.1017 0.8147 0.3754 0.027 Uiso 1 1 calc R U . . .
H4B H 0.1481 0.7793 0.2724 0.027 Uiso 1 1 calc R U . . .
C5 C 0.2234(6) 0.8757(11) 0.3735(9) 0.021(2) Uani 1 1 d . . . . .
H5A H 0.2047 0.9676 0.3606 0.025 Uiso 1 1 calc R U . . .
H5B H 0.2722 0.8581 0.3298 0.025 Uiso 1 1 calc R U . . .
C6 C 0.3226(6) 0.9480(9) 0.4978(9) 0.019(2) Uani 1 1 d . . . . .
H6A H 0.3418 0.9406 0.5677 0.029 Uiso 1 1 calc R U . . .
H6B H 0.3077 1.0403 0.4835 0.029 Uiso 1 1 calc R U . . .
H6C H 0.3671 0.9199 0.4520 0.029 Uiso 1 1 calc R U . . .
C7 C 0.1803(7) 0.9083(10) 0.5492(10) 0.024(2) Uani 1 1 d . . . . .
H7A H 0.1295 0.9198 0.5080 0.029 Uiso 1 1 calc R U . . .
H7B H 0.1952 0.9959 0.5776 0.029 Uiso 1 1 calc R U . . .
C8 C 0.1616(8) 0.8154(11) 0.6339(8) 0.023(2) Uani 1 1 d . . . . .
H8A H 0.1100 0.8454 0.6678 0.028 Uiso 1 1 calc R U . . .
H8B H 0.2073 0.8207 0.6837 0.028 Uiso 1 1 calc R U . . .
C9 C 0.1364(7) 0.5962(12) 0.6967(9) 0.027(2) Uani 1 1 d . . . . .
H9A H 0.1379 0.5013 0.6812 0.040 Uiso 1 1 calc R U . . .
H9B H 0.0819 0.6193 0.7248 0.040 Uiso 1 1 calc R U . . .
H9C H 0.1800 0.6171 0.7459 0.040 Uiso 1 1 calc R U . . .
C10 C 0.4322(8) 0.3476(13) 0.4170(8) 0.029(3) Uani 1 1 d . . . . .
H10A H 0.4630 0.3938 0.3627 0.034 Uiso 1 1 calc R U . . .
H10B H 0.3776 0.3190 0.3902 0.034 Uiso 1 1 calc R U . . .
C11 C 0.4811(7) 0.2294(12) 0.4540(9) 0.024(2) Uani 1 1 d . . . . .
H11A H 0.5406 0.2377 0.4358 0.029 Uiso 1 1 calc R U . . .
H11B H 0.4590 0.1461 0.4251 0.029 Uiso 1 1 calc R U . . .
C12 C 0.4696(7) 0.2322(10) 0.5680(8) 0.017(2) Uani 1 1 d . . . . .
H12A H 0.4183 0.1852 0.5885 0.021 Uiso 1 1 calc R U . . .
H12B H 0.5179 0.1925 0.6032 0.021 Uiso 1 1 calc R U . . .
C13 C 0.4633(6) 0.3793(10) 0.5888(8) 0.017(2) Uani 1 1 d . . . . .
H13A H 0.4313 0.3957 0.6514 0.020 Uiso 1 1 calc R U . . .
H13B H 0.5193 0.4188 0.5962 0.020 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
La1 O1 2.628(6) . ?
La1 N2 2.668(9) . ?
La1 N3 2.744(8) . ?
La1 N1 2.752(9) . ?
La1 I3 3.1337(9) . ?
La1 I2 3.1738(9) . ?
La1 I1 3.1749(9) . ?
O1 C13 1.438(12) . ?
O1 C10 1.455(13) . ?
N1 C9 1.484(14) . ?
N1 C1 1.493(13) . ?
N1 C8 1.501(14) . ?
N2 C2 1.478(13) . ?
N2 C3 1.488(14) . ?
N2 C4 1.509(14) . ?
N3 C6 1.478(12) . ?
N3 C7 1.484(14) . ?
N3 C5 1.515(14) . ?
C1 C2 1.491(15) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.509(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.493(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.510(16) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.524(14) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.513(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 La1 N2 132.3(3) . . ?
O1 La1 N3 145.4(2) . . ?
N2 La1 N3 65.1(3) . . ?
O1 La1 N1 145.4(2) . . ?
N2 La1 N1 65.9(3) . . ?
N3 La1 N1 64.8(3) . . ?
O1 La1 I3 81.46(17) . . ?
N2 La1 I3 146.2(2) . . ?
N3 La1 I3 86.90(17) . . ?
N1 La1 I3 85.72(19) . . ?
O1 La1 I2 72.39(16) . . ?
N2 La1 I2 86.13(19) . . ?
N3 La1 I2 80.92(18) . . ?
N1 La1 I2 142.19(19) . . ?
I3 La1 I2 108.76(2) . . ?
O1 La1 I1 71.62(15) . . ?
N2 La1 I1 87.85(18) . . ?
N3 La1 I1 142.91(18) . . ?
N1 La1 I1 81.55(19) . . ?
I3 La1 I1 106.44(3) . . ?
I2 La1 I1 124.13(3) . . ?
C13 O1 C10 108.9(7) . . ?
C13 O1 La1 126.8(6) . . ?
C10 O1 La1 120.0(6) . . ?
C9 N1 C1 109.1(8) . . ?
C9 N1 C8 106.9(9) . . ?
C1 N1 C8 110.1(8) . . ?
C9 N1 La1 112.6(6) . . ?
C1 N1 La1 111.9(6) . . ?
C8 N1 La1 106.0(7) . . ?
C2 N2 C3 108.5(8) . . ?
C2 N2 C4 111.0(9) . . ?
C3 N2 C4 110.2(9) . . ?
C2 N2 La1 105.9(6) . . ?
C3 N2 La1 104.8(6) . . ?
C4 N2 La1 116.0(6) . . ?
C6 N3 C7 109.5(8) . . ?
C6 N3 C5 107.0(8) . . ?
C7 N3 C5 109.8(9) . . ?
C6 N3 La1 108.8(6) . . ?
C7 N3 La1 115.7(6) . . ?
C5 N3 La1 105.6(6) . . ?
C2 C1 N1 115.0(8) . . ?
C2 C1 H1A 108.5 . . ?
N1 C1 H1A 108.5 . . ?
C2 C1 H1B 108.5 . . ?
N1 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
N2 C2 C1 114.6(9) . . ?
N2 C2 H2A 108.6 . . ?
C1 C2 H2A 108.6 . . ?
N2 C2 H2B 108.6 . . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C4 C5 114.7(9) . . ?
N2 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
N2 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C4 C5 N3 111.7(8) . . ?
C4 C5 H5A 109.3 . . ?
N3 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
N3 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
N3 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C7 C8 113.5(9) . . ?
N3 C7 H7A 108.9 . . ?
C8 C7 H7A 108.9 . . ?
N3 C7 H7B 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 N1 114.7(9) . . ?
C7 C8 H8A 108.6 . . ?
N1 C8 H8A 108.6 . . ?
C7 C8 H8B 108.6 . . ?
N1 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 C11 106.8(9) . . ?
O1 C10 H10A 110.4 . . ?
C11 C10 H10A 110.4 . . ?
O1 C10 H10B 110.4 . . ?
C11 C10 H10B 110.4 . . ?
H10A C10 H10B 108.6 . . ?
C10 C11 C12 104.2(9) . . ?
C10 C11 H11A 110.9 . . ?
C12 C11 H11A 110.9 . . ?
C10 C11 H11B 110.9 . . ?
C12 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
C13 C12 C11 102.0(9) . . ?
C13 C12 H12A 111.4 . . ?
C11 C12 H12A 111.4 . . ?
C13 C12 H12B 111.4 . . ?
C11 C12 H12B 111.4 . . ?
H12A C12 H12B 109.2 . . ?
O1 C13 C12 105.7(8) . . ?
O1 C13 H13A 110.6 . . ?
C12 C13 H13A 110.6 . . ?
O1 C13 H13B 110.6 . . ?
C12 C13 H13B 110.6 . . ?
H13A C13 H13B 108.7 . . ?

_refine_diff_density_max         3.879
_refine_diff_density_min         -1.764
_refine_diff_density_rms         0.235

####################################################################### 
# 
# 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_jcw107
_database_code_depnum_ccdc_archive 'CCDC 2236569'
loop_
_audit_author_name
_audit_author_address
'Joe Ziller'
;University of California, Irvine
United States of America
;
_audit_update_record             
;
2023-01-16 deposited with the CCDC.	2023-03-14 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            'C14 H31 Cl3 N3 O2 Y'
_chemical_formula_weight         468.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Y Y -2.7962 3.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.5589(5)
_cell_length_b                   13.5752(9)
_cell_length_c                   20.0150(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2053.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    9540
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      30.46

_exptl_crystal_description       irregular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_method    not_measured
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.377
_exptl_crystal_size_mid          0.271
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    3.240
_shelx_estimated_absorpt_T_min   0.375
_shelx_estimated_absorpt_T_max   0.523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6169
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_absorpt_special_details   
; 
Reflections not merged 
49261 Corrected reflections written to file jcw107s.hkl 
Estimated minimum and maximum transmission:  0.6169  0.7461 
The ratio (0.8268) of these values is more reliable than their absolute values 
Additional spherical absorption correction applied with mu*r =  0.2000 
Lambda/2 correction factor = 0.00150 
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49115
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.813
_diffrn_reflns_theta_max         30.549
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             6104
_reflns_number_gt                5625
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_max     0.946
_reflns_Friedel_fraction_full    0.951

_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       'Bruker APEX2 2014.11-0, 2014'
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_structure_solution    'Bruker SHELXTL 2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
A colorless crystal of approximate dimensions 0.230 x 0.271 x 0.377 mm 
was mounted in a cryoloop and transferred to a Bruker SMART APEX II 
diffractometer.  The APEX2 program package was used to determine the 
unit-cell parameters.  Data was collected using a 40 sec/frame scan time.  
The raw frame data was processed using SAINT and SADABS to yield the 
reflection data file.  Subsequent calculations were carried out using 
the SHELXTL program.  The diffraction symmetry was mmm and the systematic 
absences were consistent with the orthorhombic space group P212121 that
 was later determined to be correct.

The structure was solved by dual space methods and refined on F2 by 
full-matrix least-squares techniques.  The analytical scattering factors 
for neutral atoms were used throughout the analysis. Hydrogen atoms were 
included using a riding model.  

Least-squares analysis yielded wR2 = 0.0377 and Goof = 0.958 for 211 
variables refined against 6104 data (0.70 Å), R1 = 0.0188 for those 5625 
with I > 2.0sigma(I).  The absolute structure was assigned by refinement 
of the Flack parameter.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2228 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.0062(17)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6104
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.0188
_refine_ls_wR_factor_ref         0.0377
_refine_ls_wR_factor_gt          0.0372
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.958
_refine_ls_shift/su_max          0.001
_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
Y1 Y 0.86612(2) 0.46539(2) 0.14752(2) 0.00971(4) Uani 1 1 d . . . . .
Cl1 Cl 0.60568(6) 0.35901(3) 0.09531(2) 0.01587(10) Uani 1 1 d . . . . .
Cl2 Cl 0.69183(6) 0.56233(4) 0.23982(2) 0.01888(11) Uani 1 1 d . . . . .
Cl3 Cl 1.10880(6) 0.60472(3) 0.14434(2) 0.01782(10) Uani 1 1 d . . . . .
O1 O 1.00080(16) 0.43831(10) 0.03804(6) 0.0124(3) Uani 1 1 d . . . . .
O2 O 0.72336(17) 0.57962(10) 0.07189(7) 0.0161(3) Uani 1 1 d . . . . .
N1 N 0.8145(2) 0.32934(12) 0.23437(8) 0.0135(3) Uani 1 1 d . . . . .
N2 N 1.0477(2) 0.30482(12) 0.16007(7) 0.0114(3) Uani 1 1 d . . . . .
N3 N 1.0735(2) 0.41840(12) 0.24704(8) 0.0149(3) Uani 1 1 d . . . . .
C1 C 0.9071(2) 0.25224(14) 0.19675(9) 0.0137(4) Uani 1 1 d . . . . .
H1A H 0.8255 0.2188 0.1654 0.016 Uiso 1 1 calc R U . . .
H1B H 0.9583 0.2026 0.2273 0.016 Uiso 1 1 calc R U . . .
C2 C 0.6466(3) 0.29428(15) 0.26264(10) 0.0228(5) Uani 1 1 d . . . . .
H2A H 0.5878 0.3485 0.2861 0.034 Uiso 1 1 calc R U . . .
H2B H 0.6699 0.2405 0.2941 0.034 Uiso 1 1 calc R U . . .
H2C H 0.5700 0.2705 0.2266 0.034 Uiso 1 1 calc R U . . .
C3 C 0.9343(3) 0.36846(15) 0.28522(9) 0.0172(4) Uani 1 1 d . . . . .
H3A H 0.9845 0.3147 0.3127 0.021 Uiso 1 1 calc R U . . .
H3B H 0.8720 0.4154 0.3149 0.021 Uiso 1 1 calc R U . . .
C4 C 1.1891(3) 0.47680(16) 0.29027(10) 0.0256(5) Uani 1 1 d . . . . .
H4A H 1.2827 0.5071 0.2633 0.038 Uiso 1 1 calc R U . . .
H4B H 1.2424 0.4340 0.3242 0.038 Uiso 1 1 calc R U . . .
H4C H 1.1196 0.5284 0.3123 0.038 Uiso 1 1 calc R U . . .
C5 C 1.1735(2) 0.34525(14) 0.20878(9) 0.0152(4) Uani 1 1 d . . . . .
H5A H 1.2186 0.2927 0.2385 0.018 Uiso 1 1 calc R U . . .
H5B H 1.2750 0.3765 0.1858 0.018 Uiso 1 1 calc R U . . .
C6 C 1.1366(3) 0.23849(14) 0.11289(9) 0.0176(4) Uani 1 1 d . . . . .
H6A H 1.0551 0.2217 0.0765 0.026 Uiso 1 1 calc R U . . .
H6B H 1.1726 0.1783 0.1362 0.026 Uiso 1 1 calc R U . . .
H6C H 1.2412 0.2713 0.0944 0.026 Uiso 1 1 calc R U . . .
C7 C 0.9121(3) 0.39868(15) -0.02101(9) 0.0172(4) Uani 1 1 d . . . . .
H7A H 0.7976 0.4324 -0.0284 0.021 Uiso 1 1 calc R U . . .
H7B H 0.8901 0.3272 -0.0158 0.021 Uiso 1 1 calc R U . . .
C8 C 1.0370(3) 0.41767(18) -0.07866(10) 0.0211(5) Uani 1 1 d . . . . .
H8A H 1.0209 0.4846 -0.0973 0.025 Uiso 1 1 calc R U . . .
H8B H 1.0214 0.3685 -0.1147 0.025 Uiso 1 1 calc R U . . .
C9 C 1.2167(3) 0.40681(16) -0.04460(9) 0.0186(4) Uani 1 1 d . . . . .
H9A H 1.2476 0.3367 -0.0376 0.022 Uiso 1 1 calc R U . . .
H9B H 1.3115 0.4392 -0.0707 0.022 Uiso 1 1 calc R U . . .
C10 C 1.1847(2) 0.45888(16) 0.02077(9) 0.0149(4) Uani 1 1 d . . . . .
H10A H 1.2653 0.4335 0.0557 0.018 Uiso 1 1 calc R U . . .
H10B H 1.2040 0.5306 0.0159 0.018 Uiso 1 1 calc R U . . .
C11 C 0.5532(3) 0.62358(16) 0.08469(10) 0.0187(4) Uani 1 1 d . . . . .
H11A H 0.4996 0.5969 0.1260 0.022 Uiso 1 1 calc R U . . .
H11B H 0.4711 0.6127 0.0469 0.022 Uiso 1 1 calc R U . . .
C12 C 0.5980(3) 0.73159(15) 0.09232(10) 0.0216(5) Uani 1 1 d . . . . .
H12A H 0.6378 0.7464 0.1384 0.026 Uiso 1 1 calc R U . . .
H12B H 0.4947 0.7735 0.0816 0.026 Uiso 1 1 calc R U . . .
C13 C 0.7472(3) 0.74762(15) 0.04222(11) 0.0229(5) Uani 1 1 d . . . . .
H13A H 0.8459 0.7849 0.0627 0.027 Uiso 1 1 calc R U . . .
H13B H 0.7044 0.7840 0.0025 0.027 Uiso 1 1 calc R U . . .
C14 C 0.8057(3) 0.64324(15) 0.02336(10) 0.0187(4) Uani 1 1 d . . . . .
H14A H 0.7658 0.6264 -0.0223 0.022 Uiso 1 1 calc R U . . .
H14B H 0.9361 0.6373 0.0254 0.022 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
Y1 O2 2.4208(13) . ?
Y1 O1 2.4440(12) . ?
Y1 N1 2.5661(15) . ?
Y1 N2 2.5881(16) . ?
Y1 N3 2.6138(15) . ?
Y1 Cl2 2.6232(5) . ?
Y1 Cl3 2.6356(5) . ?
Y1 Cl1 2.6558(5) . ?
O1 C10 1.459(2) . ?
O1 C7 1.461(2) . ?
O2 C11 1.441(2) . ?
O2 C14 1.441(2) . ?
N1 C3 1.462(2) . ?
N1 C1 1.467(2) . ?
N1 C2 1.469(2) . ?
N2 C6 1.467(2) . ?
N2 C5 1.468(2) . ?
N2 C1 1.476(2) . ?
N3 C4 1.463(2) . ?
N3 C5 1.464(2) . ?
N3 C3 1.466(2) . ?
C7 C8 1.513(3) . ?
C8 C9 1.527(3) . ?
C9 C10 1.506(3) . ?
C11 C12 1.513(3) . ?
C12 C13 1.524(3) . ?
C13 C14 1.532(3) . ?

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 Y1 O1 73.82(4) . . ?
O2 Y1 N1 144.77(5) . . ?
O1 Y1 N1 124.22(5) . . ?
O2 Y1 N2 146.78(5) . . ?
O1 Y1 N2 74.90(5) . . ?
N1 Y1 N2 53.75(5) . . ?
O2 Y1 N3 154.18(5) . . ?
O1 Y1 N3 113.37(5) . . ?
N1 Y1 N3 53.08(5) . . ?
N2 Y1 N3 53.30(5) . . ?
O2 Y1 Cl2 83.98(3) . . ?
O1 Y1 Cl2 156.37(3) . . ?
N1 Y1 Cl2 78.91(4) . . ?
N2 Y1 Cl2 128.36(4) . . ?
N3 Y1 Cl2 83.51(4) . . ?
O2 Y1 Cl3 80.53(3) . . ?
O1 Y1 Cl3 78.25(3) . . ?
N1 Y1 Cl3 129.69(4) . . ?
N2 Y1 Cl3 103.75(4) . . ?
N3 Y1 Cl3 77.06(4) . . ?
Cl2 Y1 Cl3 90.371(16) . . ?
O2 Y1 Cl1 76.81(3) . . ?
O1 Y1 Cl1 82.77(3) . . ?
N1 Y1 Cl1 76.26(4) . . ?
N2 Y1 Cl1 88.47(4) . . ?
N3 Y1 Cl1 127.71(4) . . ?
Cl2 Y1 Cl1 100.232(17) . . ?
Cl3 Y1 Cl1 153.725(16) . . ?
C10 O1 C7 108.42(13) . . ?
C10 O1 Y1 125.47(10) . . ?
C7 O1 Y1 126.11(10) . . ?
C11 O2 C14 104.89(15) . . ?
C11 O2 Y1 123.51(11) . . ?
C14 O2 Y1 127.81(11) . . ?
C3 N1 C1 108.73(14) . . ?
C3 N1 C2 112.62(15) . . ?
C1 N1 C2 112.25(15) . . ?
C3 N1 Y1 96.66(11) . . ?
C1 N1 Y1 95.36(10) . . ?
C2 N1 Y1 128.72(11) . . ?
C6 N2 C5 111.11(15) . . ?
C6 N2 C1 110.67(15) . . ?
C5 N2 C1 108.48(14) . . ?
C6 N2 Y1 134.19(12) . . ?
C5 N2 Y1 95.35(10) . . ?
C1 N2 Y1 94.22(10) . . ?
C4 N3 C5 111.63(15) . . ?
C4 N3 C3 111.76(16) . . ?
C5 N3 C3 109.23(15) . . ?
C4 N3 Y1 132.58(13) . . ?
C5 N3 Y1 94.40(10) . . ?
C3 N3 Y1 94.57(10) . . ?
N1 C1 N2 104.70(14) . . ?
N1 C3 N3 104.45(14) . . ?
N3 C5 N2 105.44(14) . . ?
O1 C7 C8 105.53(15) . . ?
C7 C8 C9 101.42(15) . . ?
C10 C9 C8 101.53(15) . . ?
O1 C10 C9 105.58(15) . . ?
O2 C11 C12 102.67(16) . . ?
C11 C12 C13 103.76(17) . . ?
C12 C13 C14 104.09(16) . . ?
O2 C14 C13 105.30(16) . . ?

_refine_diff_density_max         0.470
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_jcw89
_database_code_depnum_ccdc_archive 'CCDC 2244010'
loop_
_audit_author_name
_audit_author_address
'Joe Ziller'
;University of California Irvine
United States of America
;
_audit_update_record             
;
2023-02-22 deposited with the CCDC.	2023-03-14 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            'C40 H80 F24 La4 N12 O30 S8'
_chemical_formula_weight         2477.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   15.371(5)
_cell_length_b                   15.387(5)
_cell_length_c                   18.158(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.231(5)
_cell_angle_gamma                90
_cell_volume                     4288(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    9826
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      28.29

_exptl_crystal_description       irregular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_method    not_measured
_exptl_crystal_density_diffrn    1.919
_exptl_crystal_F_000             2432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.087
_exptl_absorpt_coefficient_mu    2.277
_shelx_estimated_absorpt_T_min   0.592
_shelx_estimated_absorpt_T_max   0.827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6748
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_absorpt_special_details   
; 
Reflections not merged 
77402 Corrected reflections written to file jcw89s.hkl 
Estimated minimum and maximum transmission:  0.6748  0.7457 
The ratio (0.9049) of these values is more reliable than their absolute values 
Additional spherical absorption correction applied with mu*r =  0.2000 
Lambda/2 correction factor = 0.00150 
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            75840
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.690
_diffrn_reflns_theta_max         28.334
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10679
_reflns_number_gt                8252
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2 2014.11-0, 2014'
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_structure_solution    'Bruker SHELXTL 2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
A colorless crystal of approximate dimensions 0.087 x 0.151 x 0.257 mm 
was mounted in a cryoloop and transferred to a Bruker SMART APEX II 
diffractometer system.  The APEX2 program package was used to determine 
the unit-cell parameters and for data collection (120 sec/frame scan time).  
The raw frame data was processed using SAINT and SADABS to yield the 
reflection data file.  Subsequent calculations were carried out using 
the SHELXTL program package.  The diffraction symmetry was 2/m and the 
systematic absences were consistent with the monoclinic space group P21/n 
that was later determined to be correct.

The structure was solved by direct methods and refined on F2 by full-matrix 
least-squares techniques.  The analytical scattering factors for neutral 
atoms were used throughout the analysis.  The molecule was located about an 
inversion center.  Hydrogen atoms H(1) and H(2) were located from a 
difference-Fourier map and refined (x,y,z, riding Uiso) with d(O-H) = 0.80Å.  
The remaining hydrogen atoms were included using a riding model.  There were 
two molecules of tetrahydrofuran solvent present per tetrameric formula-unit.  
The solvent molecule exhibited high thermal motion and was refined using 
isotropic displacement parameters.

Least-squares analysis yielded wR2 = 0.1122 and Goof = 1.062 for 519 
variables refined against 10679 data (0.75 Å), R1 = 0.0394 for those 8252 
data with I > 2.0sigma(I).  
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0637P)²+5.4953P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         10679
_refine_ls_number_parameters     519
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1122
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

# start Validation Reply Form
_vrf_PLAT416_jcw89               
;
PROBLEM: Short Intra D-H..H-D H2 ..H2 . 1.81 Ang.
RESPONSE: ...The bridging hydroxide hydrogen atoms were located 
in a difference-map then refined with fixed d(O-H) = 0.80 ang.
;
_vrf_PLAT420_jcw89               
;
PROBLEM: D-H Bond Without Acceptor O1 --H1 . Please Check
RESPONSE: ...The hydroxide ligands brige the Lanthanum atoms.
There are no donar-acceptor interactions.
;
# end Validation Reply Form 

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 0.32207(2) 0.56249(2) 0.60593(2) 0.01741(7) Uani 1 1 d . . . . .
La2 La 0.40106(2) 0.69401(2) 0.44360(2) 0.01851(7) Uani 1 1 d . . . . .
S1 S 0.19717(7) 0.57520(7) 0.42586(6) 0.0246(2) Uani 1 1 d . . . . .
S2 S 0.42711(8) 0.77860(7) 0.63361(6) 0.0262(2) Uani 1 1 d . . . . .
S3 S 0.51096(7) 0.44387(7) 0.71370(6) 0.0228(2) Uani 1 1 d . . . . .
S4 S 0.34377(7) 0.31054(7) 0.57549(6) 0.0213(2) Uani 1 1 d . . . . .
F1 F 0.2270(2) 0.4496(2) 0.33462(17) 0.0404(7) Uani 1 1 d . . . . .
F2 F 0.1041(2) 0.4399(2) 0.38439(19) 0.0454(8) Uani 1 1 d . . . . .
F3 F 0.1210(2) 0.5332(2) 0.29925(17) 0.0504(9) Uani 1 1 d . . . . .
F4 F 0.58502(19) 0.7552(2) 0.69242(18) 0.0428(7) Uani 1 1 d . . . . .
F5 F 0.4992(2) 0.8227(2) 0.76086(17) 0.0516(9) Uani 1 1 d . . . . .
F6 F 0.5522(2) 0.8877(2) 0.66811(18) 0.0498(9) Uani 1 1 d . . . . .
F7 F 0.5432(2) 0.5409(3) 0.82886(19) 0.0598(10) Uani 1 1 d . . . . .
F8 F 0.6147(2) 0.5762(2) 0.7360(2) 0.0484(8) Uani 1 1 d . . . . .
F9 F 0.6517(2) 0.4635(2) 0.7989(2) 0.0515(9) Uani 1 1 d . . . . .
F10 F 0.22510(19) 0.3132(2) 0.46709(18) 0.0419(7) Uani 1 1 d . . . . .
F11 F 0.3257(2) 0.2171(2) 0.45644(18) 0.0457(8) Uani 1 1 d . . . . .
F12 F 0.3532(2) 0.3529(2) 0.43702(16) 0.0403(7) Uani 1 1 d . . . . .
O1 O 0.29484(19) 0.68776(18) 0.53306(17) 0.0215(6) Uani 1 1 d D . . . .
H1 H 0.263(2) 0.7270(16) 0.543(3) 0.026 Uiso 1 1 d D U . . .
O2 O 0.43444(19) 0.57324(19) 0.52084(17) 0.0233(6) Uani 1 1 d D . . . .
H2 H 0.4805(12) 0.549(2) 0.521(3) 0.028 Uiso 1 1 d D U . . .
O3 O 0.2367(2) 0.5213(2) 0.48355(18) 0.0328(8) Uani 1 1 d . . . . .
O4 O 0.2588(2) 0.6259(2) 0.38662(17) 0.0287(7) Uani 1 1 d . . . . .
O5 O 0.1196(2) 0.6188(3) 0.4444(2) 0.0443(10) Uani 1 1 d . . . . .
O6 O 0.4043(2) 0.6962(2) 0.66616(18) 0.0298(7) Uani 1 1 d . . . . .
O7 O 0.4632(2) 0.7720(2) 0.56167(17) 0.0290(7) Uani 1 1 d . . . . .
O8 O 0.3657(2) 0.8470(2) 0.6410(2) 0.0409(9) Uani 1 1 d . . . . .
O9 O 0.4467(2) 0.5071(2) 0.68797(18) 0.0326(8) Uani 1 1 d . . . . .
O10 O 0.4805(2) 0.3779(2) 0.7596(2) 0.0436(9) Uani 1 1 d . . . . .
O11 O 0.5660(2) 0.4144(2) 0.6574(2) 0.0375(8) Uani 1 1 d . . . . .
O12 O 0.3196(2) 0.3989(2) 0.59223(19) 0.0289(7) Uani 1 1 d . . . . .
O13 O 0.4371(2) 0.2976(2) 0.57617(19) 0.0302(7) Uani 1 1 d . . . . .
O14 O 0.2976(2) 0.2455(2) 0.6131(2) 0.0347(8) Uani 1 1 d . . . . .
N1 N 0.2557(3) 0.5305(3) 0.7424(2) 0.0309(9) Uani 1 1 d . . . . .
N2 N 0.1925(3) 0.6475(3) 0.6758(3) 0.0353(10) Uani 1 1 d . . . . .
N3 N 0.1592(2) 0.5051(3) 0.6406(2) 0.0280(8) Uani 1 1 d . . . . .
N4 N 0.4487(2) 0.8599(2) 0.4021(2) 0.0278(8) Uani 1 1 d . . . . .
N5 N 0.3574(3) 0.7853(3) 0.3160(2) 0.0333(9) Uani 1 1 d . . . . .
N6 N 0.3007(3) 0.8435(3) 0.4228(2) 0.0315(9) Uani 1 1 d . . . . .
C1 C 0.2196(3) 0.6177(4) 0.7502(3) 0.0376(12) Uani 1 1 d . . . . .
H1A H 0.2641 0.6573 0.7731 0.045 Uiso 1 1 calc R U . . .
H1B H 0.1691 0.6161 0.7817 0.045 Uiso 1 1 calc R U . . .
C2 C 0.1222(3) 0.5916(4) 0.6459(3) 0.0358(11) Uani 1 1 d . . . . .
H2A H 0.0731 0.5913 0.6789 0.043 Uiso 1 1 calc R U . . .
H2B H 0.1005 0.6125 0.5966 0.043 Uiso 1 1 calc R U . . .
C3 C 0.1861(3) 0.4736(3) 0.7133(3) 0.0324(11) Uani 1 1 d . . . . .
H3A H 0.2073 0.4130 0.7105 0.039 Uiso 1 1 calc R U . . .
H3B H 0.1364 0.4750 0.7457 0.039 Uiso 1 1 calc R U . . .
C4 C 0.2963(4) 0.4980(5) 0.8116(3) 0.0482(15) Uani 1 1 d . . . . .
H4A H 0.2519 0.4916 0.8479 0.072 Uiso 1 1 calc R U . . .
H4B H 0.3410 0.5391 0.8303 0.072 Uiso 1 1 calc R U . . .
H4C H 0.3233 0.4414 0.8032 0.072 Uiso 1 1 calc R U . . .
C5 C 0.1668(5) 0.7396(4) 0.6768(4) 0.062(2) Uani 1 1 d . . . . .
H5A H 0.1213 0.7477 0.7119 0.094 Uiso 1 1 calc R U . . .
H5B H 0.1444 0.7570 0.6274 0.094 Uiso 1 1 calc R U . . .
H5C H 0.2175 0.7753 0.6918 0.094 Uiso 1 1 calc R U . . .
C6 C 0.1001(3) 0.4449(4) 0.6007(3) 0.0450(14) Uani 1 1 d . . . . .
H6A H 0.0469 0.4383 0.6274 0.067 Uiso 1 1 calc R U . . .
H6B H 0.1286 0.3883 0.5966 0.067 Uiso 1 1 calc R U . . .
H6C H 0.0853 0.4678 0.5512 0.067 Uiso 1 1 calc R U . . .
C7 C 0.4319(3) 0.8442(3) 0.3240(3) 0.0347(11) Uani 1 1 d . . . . .
H7A H 0.4836 0.8176 0.3029 0.042 Uiso 1 1 calc R U . . .
H7B H 0.4186 0.8995 0.2979 0.042 Uiso 1 1 calc R U . . .
C8 C 0.2807(3) 0.8286(3) 0.3443(3) 0.0361(11) Uani 1 1 d . . . . .
H8A H 0.2695 0.8844 0.3184 0.043 Uiso 1 1 calc R U . . .
H8B H 0.2285 0.7913 0.3368 0.043 Uiso 1 1 calc R U . . .
C9 C 0.3738(3) 0.9045(3) 0.4320(3) 0.0306(10) Uani 1 1 d . . . . .
H9A H 0.3859 0.9188 0.4848 0.037 Uiso 1 1 calc R U . . .
H9B H 0.3606 0.9590 0.4046 0.037 Uiso 1 1 calc R U . . .
C10 C 0.5291(3) 0.9088(3) 0.4187(3) 0.0404(13) Uani 1 1 d . . . . .
H10A H 0.5243 0.9663 0.3956 0.061 Uiso 1 1 calc R U . . .
H10B H 0.5784 0.8774 0.3993 0.061 Uiso 1 1 calc R U . . .
H10C H 0.5386 0.9154 0.4722 0.061 Uiso 1 1 calc R U . . .
C11 C 0.3397(5) 0.7540(4) 0.2405(3) 0.0535(17) Uani 1 1 d . . . . .
H11A H 0.3182 0.8022 0.2092 0.080 Uiso 1 1 calc R U . . .
H11B H 0.2956 0.7081 0.2403 0.080 Uiso 1 1 calc R U . . .
H11C H 0.3934 0.7309 0.2215 0.080 Uiso 1 1 calc R U . . .
C12 C 0.2249(4) 0.8746(4) 0.4598(4) 0.0477(15) Uani 1 1 d . . . . .
H12A H 0.2072 0.9314 0.4397 0.071 Uiso 1 1 calc R U . . .
H12B H 0.2397 0.8801 0.5128 0.071 Uiso 1 1 calc R U . . .
H12C H 0.1768 0.8332 0.4518 0.071 Uiso 1 1 calc R U . . .
C13 C 0.1613(3) 0.4950(3) 0.3575(3) 0.0326(11) Uani 1 1 d . . . . .
C14 C 0.5215(4) 0.8121(3) 0.6924(3) 0.0346(11) Uani 1 1 d . . . . .
C15 C 0.5839(3) 0.5103(3) 0.7724(3) 0.0319(11) Uani 1 1 d . . . . .
C16 C 0.3100(3) 0.2985(3) 0.4775(3) 0.0310(10) Uani 1 1 d . . . . .
O15 O 0.0428(5) 0.8031(4) 0.5231(4) 0.099(2) Uiso 1 1 d . . . . .
C17 C -0.0008(10) 0.8751(10) 0.5503(8) 0.145(5) Uiso 1 1 d . . . . .
H17A H 0.0346 0.9280 0.5434 0.174 Uiso 1 1 calc R U . . .
H17B H -0.0071 0.8675 0.6039 0.174 Uiso 1 1 calc R U . . .
C18 C -0.0848(9) 0.8869(9) 0.5143(7) 0.134(4) Uiso 1 1 d . . . . .
H18A H -0.0949 0.9485 0.5007 0.161 Uiso 1 1 calc R U . . .
H18B H -0.1314 0.8672 0.5459 0.161 Uiso 1 1 calc R U . . .
C19 C -0.0806(6) 0.8292(6) 0.4452(5) 0.089(3) Uiso 1 1 d . . . . .
H19A H -0.1379 0.8036 0.4301 0.107 Uiso 1 1 calc R U . . .
H19B H -0.0571 0.8609 0.4032 0.107 Uiso 1 1 calc R U . . .
C20 C -0.0196(7) 0.7646(7) 0.4760(6) 0.101(3) Uiso 1 1 d . . . . .
H20A H -0.0517 0.7204 0.5034 0.121 Uiso 1 1 calc R U . . .
H20B H 0.0091 0.7349 0.4356 0.121 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
La1 O1 2.362(3) . ?
La1 O2 2.387(3) . ?
La1 O9 2.510(3) . ?
La1 O12 2.530(3) . ?
La1 O3 2.594(3) . ?
La1 O6 2.620(3) . ?
La1 N2 2.752(4) . ?
La1 N3 2.761(4) . ?
La1 N1 2.777(4) . ?
La1 La2 3.8289(9) . ?
La2 O2 2.367(3) . ?
La2 O1 2.369(3) . ?
La2 O13 2.537(3) 3_666 ?
La2 O11 2.551(3) 3_666 ?
La2 O4 2.588(3) . ?
La2 O7 2.592(3) . ?
La2 N5 2.761(4) . ?
La2 N4 2.771(4) . ?
La2 N6 2.783(4) . ?
S1 O5 1.424(4) . ?
S1 O3 1.443(3) . ?
S1 O4 1.446(3) . ?
S1 C13 1.813(5) . ?
S2 O8 1.426(4) . ?
S2 O6 1.451(3) . ?
S2 O7 1.452(3) . ?
S2 C14 1.826(5) . ?
S3 O10 1.410(4) . ?
S3 O11 1.437(4) . ?
S3 O9 1.444(3) . ?
S3 C15 1.817(5) . ?
S4 O14 1.423(3) . ?
S4 O12 1.446(3) . ?
S4 O13 1.448(3) . ?
S4 C16 1.834(5) . ?
F1 C13 1.315(6) . ?
F2 C13 1.334(6) . ?
F3 C13 1.332(6) . ?
F4 C14 1.312(6) . ?
F5 C14 1.318(6) . ?
F6 C14 1.339(6) . ?
F7 C15 1.317(6) . ?
F8 C15 1.315(6) . ?
F9 C15 1.334(6) . ?
F10 C16 1.328(6) . ?
F11 C16 1.336(5) . ?
F12 C16 1.318(6) . ?
O11 La2 2.551(3) 3_666 ?
O13 La2 2.537(3) 3_666 ?
N1 C3 1.459(6) . ?
N1 C4 1.460(7) . ?
N1 C1 1.462(7) . ?
N2 C2 1.461(7) . ?
N2 C1 1.465(7) . ?
N2 C5 1.471(7) . ?
N3 C3 1.445(6) . ?
N3 C2 1.454(6) . ?
N3 C6 1.460(6) . ?
N4 C7 1.448(7) . ?
N4 C10 1.464(6) . ?
N4 C9 1.471(6) . ?
N5 C7 1.462(7) . ?
N5 C11 1.462(7) . ?
N5 C8 1.471(7) . ?
N6 C12 1.458(6) . ?
N6 C8 1.460(7) . ?
N6 C9 1.467(6) . ?
O15 C20 1.382(11) . ?
O15 C17 1.399(14) . ?
C17 C18 1.425(16) . ?
C18 C19 1.541(14) . ?
C19 C20 1.456(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 La1 O2 72.11(10) . . ?
O1 La1 O9 135.66(11) . . ?
O2 La1 O9 81.47(11) . . ?
O1 La1 O12 139.10(11) . . ?
O2 La1 O12 90.72(10) . . ?
O9 La1 O12 74.14(11) . . ?
O1 La1 O3 69.79(10) . . ?
O2 La1 O3 79.15(11) . . ?
O9 La1 O3 139.26(11) . . ?
O12 La1 O3 70.65(10) . . ?
O1 La1 O6 70.08(11) . . ?
O2 La1 O6 82.32(11) . . ?
O9 La1 O6 71.64(11) . . ?
O12 La1 O6 145.71(10) . . ?
O3 La1 O6 139.27(10) . . ?
O1 La1 N2 76.13(12) . . ?
O2 La1 N2 146.55(11) . . ?
O9 La1 N2 115.87(13) . . ?
O12 La1 N2 120.74(12) . . ?
O3 La1 N2 99.61(13) . . ?
O6 La1 N2 77.23(12) . . ?
O1 La1 N3 104.75(11) . . ?
O2 La1 N3 150.25(11) . . ?
O9 La1 N3 115.33(12) . . ?
O12 La1 N3 72.26(11) . . ?
O3 La1 N3 72.30(12) . . ?
O6 La1 N3 125.32(11) . . ?
N2 La1 N3 50.04(12) . . ?
O1 La1 N1 125.61(11) . . ?
O2 La1 N1 154.90(11) . . ?
O9 La1 N1 73.53(12) . . ?
O12 La1 N1 84.67(12) . . ?
O3 La1 N1 121.85(12) . . ?
O6 La1 N1 87.67(11) . . ?
N2 La1 N1 50.28(13) . . ?
N3 La1 N1 49.93(12) . . ?
O1 La1 La2 36.03(7) . . ?
O2 La1 La2 36.17(7) . . ?
O9 La1 La2 111.84(8) . . ?
O12 La1 La2 116.99(8) . . ?
O3 La1 La2 68.70(8) . . ?
O6 La1 La2 74.94(8) . . ?
N2 La1 La2 111.89(9) . . ?
N3 La1 La2 132.50(9) . . ?
N1 La1 La2 158.31(9) . . ?
O2 La2 O1 72.34(10) . . ?
O2 La2 O13 86.70(10) . 3_666 ?
O1 La2 O13 144.92(11) . 3_666 ?
O2 La2 O11 82.37(12) . 3_666 ?
O1 La2 O11 129.70(11) . 3_666 ?
O13 La2 O11 72.28(11) 3_666 3_666 ?
O2 La2 O4 93.95(10) . . ?
O1 La2 O4 70.02(10) . . ?
O13 La2 O4 141.03(11) 3_666 . ?
O11 La2 O4 69.22(11) 3_666 . ?
O2 La2 O7 79.40(11) . . ?
O1 La2 O7 71.82(10) . . ?
O13 La2 O7 76.97(11) 3_666 . ?
O11 La2 O7 144.93(11) 3_666 . ?
O4 La2 O7 141.46(10) . . ?
O2 La2 N5 158.64(12) . . ?
O1 La2 N5 116.87(12) . . ?
O13 La2 N5 92.82(12) 3_666 . ?
O11 La2 N5 77.17(13) 3_666 . ?
O4 La2 N5 73.16(12) . . ?
O7 La2 N5 121.31(12) . . ?
O2 La2 N4 146.34(11) . . ?
O1 La2 N4 115.25(10) . . ?
O13 La2 N4 68.80(11) 3_666 . ?
O11 La2 N4 109.93(12) 3_666 . ?
O4 La2 N4 119.65(11) . . ?
O7 La2 N4 72.99(11) . . ?
N5 La2 N4 50.11(12) . . ?
O2 La2 N6 146.00(11) . . ?
O1 La2 N6 74.23(11) . . ?
O13 La2 N6 118.63(11) 3_666 . ?
O11 La2 N6 125.03(12) 3_666 . ?
O4 La2 N6 80.28(12) . . ?
O7 La2 N6 84.56(12) . . ?
N5 La2 N6 50.14(12) . . ?
N4 La2 N6 49.84(12) . . ?
O2 La2 La1 36.53(7) . . ?
O1 La2 La1 35.91(7) . . ?
O13 La2 La1 119.47(8) 3_666 . ?
O11 La2 La1 106.98(9) 3_666 . ?
O4 La2 La1 78.24(7) . . ?
O7 La2 La1 74.11(8) . . ?
N5 La2 La1 147.42(10) . . ?
N4 La2 La1 142.76(8) . . ?
N6 La2 La1 110.10(9) . . ?
O5 S1 O3 115.0(2) . . ?
O5 S1 O4 116.3(2) . . ?
O3 S1 O4 114.0(2) . . ?
O5 S1 C13 104.8(2) . . ?
O3 S1 C13 101.8(2) . . ?
O4 S1 C13 102.3(2) . . ?
O8 S2 O6 115.5(2) . . ?
O8 S2 O7 115.2(2) . . ?
O6 S2 O7 114.8(2) . . ?
O8 S2 C14 104.2(2) . . ?
O6 S2 C14 102.2(2) . . ?
O7 S2 C14 102.4(2) . . ?
O10 S3 O11 114.9(2) . . ?
O10 S3 O9 115.6(2) . . ?
O11 S3 O9 113.7(2) . . ?
O10 S3 C15 105.8(2) . . ?
O11 S3 C15 103.1(2) . . ?
O9 S3 C15 101.5(2) . . ?
O14 S4 O12 114.8(2) . . ?
O14 S4 O13 114.8(2) . . ?
O12 S4 O13 113.18(19) . . ?
O14 S4 C16 105.8(2) . . ?
O12 S4 C16 103.7(2) . . ?
O13 S4 C16 102.7(2) . . ?
La1 O1 La2 108.06(11) . . ?
La2 O2 La1 107.29(11) . . ?
S1 O3 La1 130.78(19) . . ?
S1 O4 La2 125.73(18) . . ?
S2 O6 La1 129.67(19) . . ?
S2 O7 La2 129.39(18) . . ?
S3 O9 La1 155.0(2) . . ?
S3 O11 La2 150.1(2) . 3_666 ?
S4 O12 La1 162.5(2) . . ?
S4 O13 La2 166.2(2) . 3_666 ?
C3 N1 C4 112.1(4) . . ?
C3 N1 C1 108.1(4) . . ?
C4 N1 C1 112.1(4) . . ?
C3 N1 La1 94.7(3) . . ?
C4 N1 La1 131.9(3) . . ?
C1 N1 La1 94.9(3) . . ?
C2 N2 C1 109.0(4) . . ?
C2 N2 C5 112.2(5) . . ?
C1 N2 C5 110.7(5) . . ?
C2 N2 La1 95.0(3) . . ?
C1 N2 La1 95.8(3) . . ?
C5 N2 La1 131.7(4) . . ?
C3 N3 C2 109.8(4) . . ?
C3 N3 C6 112.3(4) . . ?
C2 N3 C6 112.3(4) . . ?
C3 N3 La1 95.7(3) . . ?
C2 N3 La1 94.9(3) . . ?
C6 N3 La1 129.5(3) . . ?
C7 N4 C10 112.9(4) . . ?
C7 N4 C9 109.8(4) . . ?
C10 N4 C9 110.7(4) . . ?
C7 N4 La2 94.4(3) . . ?
C10 N4 La2 130.6(3) . . ?
C9 N4 La2 96.1(3) . . ?
C7 N5 C11 113.6(5) . . ?
C7 N5 C8 108.8(4) . . ?
C11 N5 C8 111.5(4) . . ?
C7 N5 La2 94.6(3) . . ?
C11 N5 La2 130.0(3) . . ?
C8 N5 La2 95.7(3) . . ?
C12 N6 C8 111.9(4) . . ?
C12 N6 C9 111.3(4) . . ?
C8 N6 C9 109.2(4) . . ?
C12 N6 La2 131.3(3) . . ?
C8 N6 La2 95.0(3) . . ?
C9 N6 La2 95.7(2) . . ?
N1 C1 N2 106.7(4) . . ?
N3 C2 N2 106.3(4) . . ?
N3 C3 N1 107.2(4) . . ?
N4 C7 N5 107.3(4) . . ?
N6 C8 N5 106.5(4) . . ?
N6 C9 N4 105.6(4) . . ?
F1 C13 F3 108.3(4) . . ?
F1 C13 F2 108.2(4) . . ?
F3 C13 F2 106.5(4) . . ?
F1 C13 S1 111.6(3) . . ?
F3 C13 S1 110.7(3) . . ?
F2 C13 S1 111.3(4) . . ?
F4 C14 F5 108.4(4) . . ?
F4 C14 F6 107.7(4) . . ?
F5 C14 F6 108.6(4) . . ?
F4 C14 S2 112.2(3) . . ?
F5 C14 S2 110.2(4) . . ?
F6 C14 S2 109.6(3) . . ?
F8 C15 F7 108.5(4) . . ?
F8 C15 F9 107.5(4) . . ?
F7 C15 F9 107.9(4) . . ?
F8 C15 S3 111.5(4) . . ?
F7 C15 S3 110.7(3) . . ?
F9 C15 S3 110.5(3) . . ?
F12 C16 F10 109.5(4) . . ?
F12 C16 F11 109.3(4) . . ?
F10 C16 F11 108.1(4) . . ?
F12 C16 S4 110.7(3) . . ?
F10 C16 S4 110.1(3) . . ?
F11 C16 S4 109.1(3) . . ?
C20 O15 C17 103.2(9) . . ?
O15 C17 C18 112.2(12) . . ?
C17 C18 C19 102.8(11) . . ?
C20 C19 C18 97.8(9) . . ?
O15 C20 C19 110.7(9) . . ?

_refine_diff_density_max         1.935
_refine_diff_density_min         -1.211
_refine_diff_density_rms         0.160

