# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1472564'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2016-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '3(C6 H11 N2), Cl6 Sc'
_chemical_formula_sum            'C18 H33 Cl6 N6 Sc'
_chemical_formula_weight         591.16

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'
Sc Sc 0.2519 0.3716 '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+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   19.4113(17)
_cell_length_b                   13.0587(12)
_cell_length_c                   11.0459(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2800.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4799
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.5

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.853
_shelx_estimated_absorpt_T_min   0.920
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.739
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Sealed Tube'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            15098
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.120
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.806
_diffrn_reflns_point_group_measured_fraction_full 0.806
_reflns_number_total             5189
_reflns_number_gt                4854
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.537
_reflns_Friedel_fraction_max     0.594
_reflns_Friedel_fraction_full    0.594

_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       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_structure_solution    'SUPERFLIP (Palatinus and Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-III (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2003), WinGX (Farrugia, 1999) and enCIFer (Allen et al., 2004).'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0392P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1639 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.12(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5189
_refine_ls_number_parameters     286
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0642
_refine_ls_wR_factor_gt          0.0626
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
C1 C 0.41215(14) -0.4093(2) -0.9217(3) 0.0286(6) Uani 1 1 d . . . . .
H1 H 0.3866 -0.3786 -0.9855 0.034 Uiso 1 1 calc R U . . .
C2 C 0.47308(15) -0.4308(2) -0.7565(3) 0.0408(7) Uani 1 1 d . . . . .
H2 H 0.4977 -0.4165 -0.6840 0.049 Uiso 1 1 calc R U . . .
C3 C 0.46255(17) -0.5230(3) -0.8048(3) 0.0405(7) Uani 1 1 d . . . . .
H3 H 0.4785 -0.5865 -0.7736 0.049 Uiso 1 1 calc R U . . .
C4 C 0.4427(2) -0.2480(2) -0.8133(3) 0.0398(8) Uani 1 1 d . . . . .
H4A H 0.4195 -0.2306 -0.7362 0.048 Uiso 1 1 calc R U . . .
H4B H 0.4169 -0.2148 -0.8800 0.048 Uiso 1 1 calc R U . . .
C5 C 0.5156(2) -0.2082(3) -0.8112(3) 0.0506(9) Uani 1 1 d . . . . .
H5A H 0.5390 -0.2274 -0.8865 0.076 Uiso 1 1 calc R U . . .
H5B H 0.5403 -0.2379 -0.7422 0.076 Uiso 1 1 calc R U . . .
H5C H 0.5150 -0.1334 -0.8036 0.076 Uiso 1 1 calc R U . . .
C6 C 0.39586(18) -0.5911(2) -0.9840(3) 0.0371(7) Uani 1 1 d . . . . .
H6A H 0.3835 -0.5634 -1.0635 0.056 Uiso 1 1 calc R U . . .
H6B H 0.3547 -0.6195 -0.9451 0.056 Uiso 1 1 calc R U . . .
H6C H 0.4304 -0.6453 -0.9940 0.056 Uiso 1 1 calc R U . . .
C7 C 0.17722(17) 0.0769(3) -1.0756(3) 0.0419(8) Uani 1 1 d . . . . .
H7 H 0.1634 0.1187 -1.0095 0.050 Uiso 1 1 calc R U . . .
C8 C 0.22357(17) 0.0234(3) -1.2439(3) 0.0504(9) Uani 1 1 d . . . . .
H8 H 0.2486 0.0228 -1.3178 0.060 Uiso 1 1 calc R U . . .
C9 C 0.19505(19) -0.0567(3) -1.1902(3) 0.0455(9) Uani 1 1 d . . . . .
H9 H 0.1946 -0.1251 -1.2196 0.055 Uiso 1 1 calc R U . . .
C10 C 0.2294(2) 0.2176(4) -1.1982(4) 0.0620(11) Uani 1 1 d . . . . .
H10A H 0.2136 0.2368 -1.2804 0.074 Uiso 1 1 calc R U . . .
H10B H 0.2067 0.2635 -1.1391 0.074 Uiso 1 1 calc R U . . .
C11 C 0.3056(3) 0.2296(4) -1.1898(5) 0.0818(15) Uani 1 1 d . . . . .
H11A H 0.3278 0.1859 -1.2505 0.123 Uiso 1 1 calc R U . . .
H11B H 0.3210 0.2094 -1.1088 0.123 Uiso 1 1 calc R U . . .
H11C H 0.3180 0.3012 -1.2046 0.123 Uiso 1 1 calc R U . . .
C12 C 0.1298(3) -0.0886(4) -1.0004(4) 0.0667(13) Uani 1 1 d . . . . .
H12A H 0.0891 -0.1176 -1.0402 0.100 Uiso 1 1 calc R U . . .
H12B H 0.1154 -0.0482 -0.9300 0.100 Uiso 1 1 calc R U . . .
H12C H 0.1603 -0.1441 -0.9739 0.100 Uiso 1 1 calc R U . . .
C13 C 0.42734(15) 0.0824(2) -0.8259(3) 0.0296(6) Uani 1 1 d . . . . .
H13 H 0.4670 0.1111 -0.7886 0.036 Uiso 1 1 calc R U . . .
C14 C 0.32065(16) 0.0337(2) -0.8598(3) 0.0380(7) Uani 1 1 d . . . . .
H14 H 0.2726 0.0227 -0.8494 0.046 Uiso 1 1 calc R U . . .
C15 C 0.35889(16) 0.0052(2) -0.9560(3) 0.0370(7) Uani 1 1 d . . . . .
H15 H 0.3429 -0.0295 -1.0262 0.044 Uiso 1 1 calc R U . . .
C16 C 0.34399(17) 0.1218(3) -0.6604(3) 0.0439(8) Uani 1 1 d . . . . .
H16A H 0.3056 0.1710 -0.6705 0.053 Uiso 1 1 calc R U . . .
H16B H 0.3834 0.1590 -0.6243 0.053 Uiso 1 1 calc R U . . .
C17 C 0.3219(2) 0.0373(4) -0.5760(4) 0.0727(14) Uani 1 1 d . . . . .
H17A H 0.2787 0.0072 -0.6053 0.109 Uiso 1 1 calc R U . . .
H17B H 0.3148 0.0653 -0.4947 0.109 Uiso 1 1 calc R U . . .
H17C H 0.3577 -0.0156 -0.5733 0.109 Uiso 1 1 calc R U . . .
C18 C 0.48504(15) 0.0212(2) -1.0134(3) 0.0359(7) Uani 1 1 d . . . . .
H18A H 0.4825 0.0698 -1.0809 0.054 Uiso 1 1 calc R U . . .
H18B H 0.4846 -0.0489 -1.0450 0.054 Uiso 1 1 calc R U . . .
H18C H 0.5277 0.0326 -0.9680 0.054 Uiso 1 1 calc R U . . .
N1 N 0.44192(13) -0.36001(19) -0.8305(2) 0.0312(5) Uani 1 1 d . . . . .
N2 N 0.42428(12) -0.50927(17) -0.9084(2) 0.0289(5) Uani 1 1 d . . . . .
N3 N 0.21010(15) 0.1085(2) -1.1724(2) 0.0466(7) Uani 1 1 d . . . . .
N4 N 0.16649(16) -0.0229(2) -1.0852(3) 0.0398(7) Uani 1 1 d . . . . .
N5 N 0.36414(12) 0.08148(18) -0.7794(2) 0.0303(5) Uani 1 1 d . . . . .
N6 N 0.42576(13) 0.03624(17) -0.9332(2) 0.0282(5) Uani 1 1 d . . . . .
Cl2 Cl 0.73348(4) 0.22876(5) -0.88173(6) 0.02821(15) Uani 1 1 d . . . . .
Cl3 Cl 0.69395(4) 0.22846(5) -0.56413(6) 0.02626(14) Uani 1 1 d . . . . .
Cl4 Cl 0.64388(3) 0.43169(4) -0.74346(6) 0.02709(14) Uani 1 1 d . . . . .
Cl5 Cl 0.55738(4) 0.26557(5) -0.94874(7) 0.02937(16) Uani 1 1 d . . . . .
Cl6 Cl 0.60924(3) 0.05449(4) -0.76966(6) 0.02640(14) Uani 1 1 d . . . . .
Cl7 Cl 0.51753(4) 0.25656(5) -0.63706(7) 0.02497(14) Uani 1 1 d . . . . .
Sc1 Sc 0.62714(3) 0.24178(3) -0.75840(6) 0.01973(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.327(4) . ?
C1 N2 1.335(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.334(5) . ?
C2 N1 1.374(4) . ?
C2 H2 0.9500 . ?
C3 N2 1.376(4) . ?
C3 H3 0.9500 . ?
C4 N1 1.475(4) . ?
C4 C5 1.509(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 N2 1.465(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 N3 1.312(4) . ?
C7 N4 1.323(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.324(5) . ?
C8 N3 1.388(4) . ?
C8 H8 0.9500 . ?
C9 N4 1.360(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.489(6) . ?
C10 N3 1.501(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N4 1.456(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N5 1.330(4) . ?
C13 N6 1.330(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.349(4) . ?
C14 N5 1.375(4) . ?
C14 H14 0.9500 . ?
C15 N6 1.383(4) . ?
C15 H15 0.9500 . ?
C16 N5 1.470(4) . ?
C16 C17 1.506(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N6 1.466(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
Cl2 Sc1 2.4790(10) . ?
Cl3 Sc1 2.5134(10) . ?
Cl4 Sc1 2.5066(7) . ?
Cl5 Sc1 2.5200(10) . ?
Cl6 Sc1 2.4735(8) . ?
Cl7 Sc1 2.5220(10) . ?

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 C1 N2 108.3(3) . . ?
N1 C1 H1 125.9 . . ?
N2 C1 H1 125.9 . . ?
C3 C2 N1 107.6(3) . . ?
C3 C2 H2 126.2 . . ?
N1 C2 H2 126.2 . . ?
C2 C3 N2 107.3(3) . . ?
C2 C3 H3 126.3 . . ?
N2 C3 H3 126.3 . . ?
N1 C4 C5 110.6(3) . . ?
N1 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C7 N4 108.7(3) . . ?
N3 C7 H7 125.6 . . ?
N4 C7 H7 125.6 . . ?
C9 C8 N3 107.4(3) . . ?
C9 C8 H8 126.3 . . ?
N3 C8 H8 126.3 . . ?
C8 C9 N4 107.2(3) . . ?
C8 C9 H9 126.4 . . ?
N4 C9 H9 126.4 . . ?
C11 C10 N3 109.6(4) . . ?
C11 C10 H10A 109.8 . . ?
N3 C10 H10A 109.8 . . ?
C11 C10 H10B 109.8 . . ?
N3 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N4 C12 H12A 109.5 . . ?
N4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N5 C13 N6 108.6(3) . . ?
N5 C13 H13 125.7 . . ?
N6 C13 H13 125.7 . . ?
C15 C14 N5 107.2(3) . . ?
C15 C14 H14 126.4 . . ?
N5 C14 H14 126.4 . . ?
C14 C15 N6 107.0(3) . . ?
C14 C15 H15 126.5 . . ?
N6 C15 H15 126.5 . . ?
N5 C16 C17 111.5(3) . . ?
N5 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
N5 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N6 C18 H18A 109.5 . . ?
N6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 N1 C2 108.5(2) . . ?
C1 N1 C4 125.6(3) . . ?
C2 N1 C4 125.9(3) . . ?
C1 N2 C3 108.3(3) . . ?
C1 N2 C6 125.8(3) . . ?
C3 N2 C6 125.6(3) . . ?
C7 N3 C8 107.7(3) . . ?
C7 N3 C10 125.1(3) . . ?
C8 N3 C10 127.2(3) . . ?
C7 N4 C9 108.9(3) . . ?
C7 N4 C12 127.2(3) . . ?
C9 N4 C12 123.8(3) . . ?
C13 N5 C14 108.8(2) . . ?
C13 N5 C16 126.0(2) . . ?
C14 N5 C16 125.2(3) . . ?
C13 N6 C15 108.5(3) . . ?
C13 N6 C18 125.6(3) . . ?
C15 N6 C18 126.0(2) . . ?
Cl6 Sc1 Cl2 91.23(3) . . ?
Cl6 Sc1 Cl4 178.91(4) . . ?
Cl2 Sc1 Cl4 89.77(3) . . ?
Cl6 Sc1 Cl3 92.69(3) . . ?
Cl2 Sc1 Cl3 91.99(3) . . ?
Cl4 Sc1 Cl3 86.87(3) . . ?
Cl6 Sc1 Cl5 90.26(3) . . ?
Cl2 Sc1 Cl5 89.85(3) . . ?
Cl4 Sc1 Cl5 90.15(3) . . ?
Cl3 Sc1 Cl5 176.49(3) . . ?
Cl6 Sc1 Cl7 89.08(3) . . ?
Cl2 Sc1 Cl7 178.71(4) . . ?
Cl4 Sc1 Cl7 89.93(3) . . ?
Cl3 Sc1 Cl7 89.24(3) . . ?
Cl5 Sc1 Cl7 88.89(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 -0.5(4) . . . . ?
N3 C8 C9 N4 -2.1(4) . . . . ?
N5 C14 C15 N6 0.0(4) . . . . ?
N2 C1 N1 C2 -0.8(3) . . . . ?
N2 C1 N1 C4 178.0(3) . . . . ?
C3 C2 N1 C1 0.8(4) . . . . ?
C3 C2 N1 C4 -177.9(3) . . . . ?
C5 C4 N1 C1 -120.1(3) . . . . ?
C5 C4 N1 C2 58.4(4) . . . . ?
N1 C1 N2 C3 0.4(3) . . . . ?
N1 C1 N2 C6 174.7(3) . . . . ?
C2 C3 N2 C1 0.1(4) . . . . ?
C2 C3 N2 C6 -174.3(3) . . . . ?
N4 C7 N3 C8 -2.9(4) . . . . ?
N4 C7 N3 C10 177.5(3) . . . . ?
C9 C8 N3 C7 3.1(4) . . . . ?
C9 C8 N3 C10 -177.3(3) . . . . ?
C11 C10 N3 C7 110.7(4) . . . . ?
C11 C10 N3 C8 -68.9(5) . . . . ?
N3 C7 N4 C9 1.6(4) . . . . ?
N3 C7 N4 C12 -177.7(4) . . . . ?
C8 C9 N4 C7 0.4(4) . . . . ?
C8 C9 N4 C12 179.7(4) . . . . ?
N6 C13 N5 C14 -0.3(3) . . . . ?
N6 C13 N5 C16 177.9(3) . . . . ?
C15 C14 N5 C13 0.2(4) . . . . ?
C15 C14 N5 C16 -178.1(3) . . . . ?
C17 C16 N5 C13 -112.9(4) . . . . ?
C17 C16 N5 C14 65.1(4) . . . . ?
N5 C13 N6 C15 0.3(3) . . . . ?
N5 C13 N6 C18 -179.8(3) . . . . ?
C14 C15 N6 C13 -0.2(4) . . . . ?
C14 C15 N6 C18 179.9(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
C9 H9 Cl2 0.95 2.64 3.383(3) 135.1 2_654
C13 H13 Cl6 0.95 2.87 3.604(3) 135.2 .
C13 H13 Cl7 0.95 2.72 3.548(3) 146.8 .
C7 H7 Cl2 0.95 2.80 3.496(3) 131.3 4_455
C7 H7 Cl5 0.95 2.64 3.407(3) 138.1 4_455
C14 H14 Cl4 0.95 2.82 3.692(3) 152.5 4_455
C15 H15 Cl3 0.95 2.73 3.434(3) 131.7 2_654
C15 H15 Cl6 0.95 2.86 3.604(3) 135.6 2_654
C1 H1 Cl3 0.95 2.65 3.506(3) 149.5 2_654
C3 H3 Cl5 0.95 3.13 3.679(3) 118.2 1_545
C3 H3 Cl7 0.95 2.65 3.586(3) 166.7 1_545

_refine_diff_density_max         0.375
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_2014rmjdc1091a_ml
_database_code_depnum_ccdc_archive 'CCDC 1472565'
_audit_update_record             
;
2016-04-06 deposited with the CCDC.
2016-06-20 downloaded from the CCDC.
;
_audit_creation_date             2014-05-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '3(C6 H11 N2), Cl6 Y'
_chemical_formula_sum            'C18 H33 Cl6 N6 Y'
_chemical_formula_weight         635.11
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
Y Y -2.7962 3.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   19.580(2)
_cell_length_b                   13.0359(15)
_cell_length_c                   11.1656(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2849.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6036
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      2.6
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.626
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14268
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.557
_diffrn_reflns_theta_min         2.602
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.020183
_diffrn_orient_matrix_UB_12      -0.050450
_diffrn_orient_matrix_UB_13      -0.071194
_diffrn_orient_matrix_UB_21      -0.050571
_diffrn_orient_matrix_UB_22      0.039322
_diffrn_orient_matrix_UB_23      -0.042201
_diffrn_orient_matrix_UB_31      0.036637
_diffrn_orient_matrix_UB_32      0.033095
_diffrn_orient_matrix_UB_33      -0.013066
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           55.0
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_full    0.946
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                5049
_reflns_number_total             6374
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 1920 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.797
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         6374
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0282
_refine_ls_restrained_S_all      0.797
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0088P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0454
_refine_ls_wR_factor_ref         0.0479
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C4(H4A,H4B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C1(H1), C3(H3), C2(H2), C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C),
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.36511(15) 0.0756(2) 0.3978(3) 0.0234(8) Uani 1 1 d . . . . .
N4 N 0.42611(17) 0.0344(3) 0.5509(4) 0.0228(9) Uani 1 1 d . . . . .
C7 C 0.4276(2) 0.0775(4) 0.4446(4) 0.0236(11) Uani 1 1 d . . . . .
H7 H 0.4669 0.1055 0.4071 0.028 Uiso 1 1 calc R . . . .
C8 C 0.3221(2) 0.0305(3) 0.4799(4) 0.0283(11) Uani 1 1 d . . . . .
H8 H 0.2743 0.0200 0.4709 0.034 Uiso 1 1 calc R . . . .
C9 C 0.3601(2) 0.0043(3) 0.5750(4) 0.0277(10) Uani 1 1 d . . . . .
H9 H 0.3444 -0.0287 0.6456 0.033 Uiso 1 1 calc R . . . .
C10 C 0.3453(2) 0.1125(4) 0.2789(4) 0.0367(12) Uani 1 1 d . . . . .
H10A H 0.3844 0.1487 0.2419 0.044 Uiso 1 1 calc R . . . .
H10B H 0.3073 0.1621 0.2870 0.044 Uiso 1 1 calc R . . . .
C11 C 0.3233(3) 0.0252(5) 0.1986(5) 0.0535(18) Uani 1 1 d . . . . .
H11A H 0.3587 -0.0280 0.1982 0.080 Uiso 1 1 calc GR . . . .
H11B H 0.3165 0.0508 0.1170 0.080 Uiso 1 1 calc GR . . . .
H11C H 0.2805 -0.0040 0.2286 0.080 Uiso 1 1 calc GR . . . .
C12 C 0.48518(19) 0.0214(3) 0.6314(4) 0.0280(11) Uani 1 1 d . . . . .
H12A H 0.4855 -0.0487 0.6632 0.042 Uiso 1 1 calc GR . . . .
H12B H 0.4818 0.0702 0.6978 0.042 Uiso 1 1 calc GR . . . .
H12C H 0.5275 0.0339 0.5868 0.042 Uiso 1 1 calc GR . . . .
Y1 Y 0.37045(2) 0.75835(3) 0.87838(8) 0.01774(8) Uani 1 1 d . . . . .
Cl1 Cl 0.48533(5) 0.74420(8) 0.75330(10) 0.0212(2) Uani 1 1 d . . . . .
Cl2 Cl 0.39017(4) 0.95648(7) 0.88847(13) 0.0223(2) Uani 1 1 d . . . . .
Cl3 Cl 0.25926(5) 0.76917(9) 1.00808(10) 0.0240(2) Uani 1 1 d . . . . .
Cl4 Cl 0.35344(5) 0.55788(7) 0.86249(12) 0.0234(2) Uani 1 1 d . . . . .
Cl5 Cl 0.44191(5) 0.73356(9) 1.07800(10) 0.0251(3) Uani 1 1 d . . . . .
Cl6 Cl 0.30127(5) 0.76915(9) 0.67452(9) 0.0230(2) Uani 1 1 d . . . . .
N1 N 0.44080(17) 0.6373(3) 0.4495(3) 0.0239(8) Uani 1 1 d . . . . .
N2 N 0.42502(17) 0.4881(3) 0.5280(4) 0.0230(9) Uani 1 1 d . . . . .
N5 N 0.28908(18) 0.6069(3) 0.2960(4) 0.0336(10) Uani 1 1 d . . . . .
N6 N 0.33237(19) 0.4750(3) 0.2077(4) 0.0303(10) Uani 1 1 d . . . . .
C1 C 0.41283(19) 0.5876(3) 0.5414(4) 0.0226(10) Uani 1 1 d . . . . .
H1 H 0.3883 0.6182 0.6055 0.027 Uiso 1 1 calc R . . . .
C3 C 0.4621(2) 0.4742(4) 0.4251(4) 0.0321(12) Uani 1 1 d . . . . .
H3 H 0.4781 0.4107 0.3941 0.038 Uiso 1 1 calc R . . . .
C2 C 0.47132(18) 0.5666(3) 0.3766(5) 0.0319(10) Uani 1 1 d . . . . .
H2 H 0.4950 0.5808 0.3042 0.038 Uiso 1 1 calc R . . . .
C4 C 0.4411(2) 0.7496(3) 0.4320(4) 0.0309(10) Uani 1 1 d . . . . .
H4A H 0.4156 0.7828 0.4980 0.037 Uiso 1 1 calc R . . . .
H4B H 0.4178 0.7665 0.3558 0.037 Uiso 1 1 calc R . . . .
C5 C 0.5135(2) 0.7908(4) 0.4291(4) 0.0363(12) Uani 1 1 d . . . . .
H5A H 0.5387 0.7585 0.3632 0.054 Uiso 1 1 calc GR . . . .
H5B H 0.5363 0.7753 0.5051 0.054 Uiso 1 1 calc GR . . . .
H5C H 0.5125 0.8652 0.4170 0.054 Uiso 1 1 calc GR . . . .
C6 C 0.3985(2) 0.4064(4) 0.6049(4) 0.0287(11) Uani 1 1 d . . . . .
H6A H 0.3855 0.4351 0.6827 0.043 Uiso 1 1 calc GR . . . .
H6B H 0.4338 0.3540 0.6163 0.043 Uiso 1 1 calc GR . . . .
H6C H 0.3583 0.3752 0.5670 0.043 Uiso 1 1 calc GR . . . .
C13 C 0.3213(2) 0.5743(4) 0.1989(4) 0.0336(12) Uani 1 1 d . . . . .
H13 H 0.3344 0.6161 0.1331 0.040 Uiso 1 1 calc R . . . .
C14 C 0.2786(2) 0.5231(4) 0.3690(5) 0.0370(12) Uani 1 1 d . . . . .
H14 H 0.2559 0.5234 0.4441 0.044 Uiso 1 1 calc R . . . .
C15 C 0.3061(2) 0.4419(4) 0.3157(5) 0.0330(13) Uani 1 1 d . . . . .
H15 H 0.3073 0.3739 0.3461 0.040 Uiso 1 1 calc R . . . .
C16 C 0.2685(2) 0.7144(4) 0.3209(5) 0.0440(13) Uani 1 1 d . . . . .
H16A H 0.2903 0.7607 0.2618 0.053 Uiso 1 1 calc R . . . .
H16B H 0.2846 0.7345 0.4016 0.053 Uiso 1 1 calc R . . . .
C17 C 0.1925(2) 0.7262(4) 0.3145(5) 0.0515(15) Uani 1 1 d . . . . .
H17A H 0.1768 0.7100 0.2333 0.077 Uiso 1 1 calc GR . . . .
H17B H 0.1800 0.7970 0.3342 0.077 Uiso 1 1 calc GR . . . .
H17C H 0.1709 0.6793 0.3717 0.077 Uiso 1 1 calc GR . . . .
C18 C 0.3689(3) 0.4087(5) 0.1227(5) 0.0456(15) Uani 1 1 d . . . . .
H18A H 0.4081 0.3771 0.1629 0.068 Uiso 1 1 calc GR . . . .
H18B H 0.3849 0.4499 0.0549 0.068 Uiso 1 1 calc GR . . . .
H18C H 0.3380 0.3550 0.0937 0.068 Uiso 1 1 calc GR . . . .


_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
N3 C7 1.330(5) . ?
N3 C8 1.377(5) . ?
N3 C10 1.464(5) . ?
N4 C7 1.314(6) . ?
N4 C9 1.377(5) . ?
N4 C12 1.475(5) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.340(6) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.513(7) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
Y1 Cl1 2.6541(12) . ?
Y1 Cl2 2.6140(10) . ?
Y1 Cl3 2.6185(12) . ?
Y1 Cl4 2.6404(10) . ?
Y1 Cl5 2.6515(14) . ?
Y1 Cl6 2.6524(14) . ?
N1 C1 1.331(5) . ?
N1 C2 1.367(5) . ?
N1 C4 1.477(5) . ?
N2 C1 1.328(5) . ?
N2 C3 1.371(6) . ?
N2 C6 1.463(6) . ?
N5 C13 1.324(6) . ?
N5 C14 1.378(6) . ?
N5 C16 1.485(6) . ?
N6 C13 1.317(6) . ?
N6 C15 1.380(6) . ?
N6 C18 1.469(6) . ?
C1 H1 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.332(6) . ?
C2 H2 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.517(6) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.328(7) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.499(6) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N3 C8 108.1(4) . . ?
C7 N3 C10 126.3(3) . . ?
C8 N3 C10 125.6(3) . . ?
C7 N4 C9 108.6(4) . . ?
C7 N4 C12 125.7(4) . . ?
C9 N4 C12 125.8(4) . . ?
N3 C7 H7 125.5 . . ?
N4 C7 N3 109.0(4) . . ?
N4 C7 H7 125.5 . . ?
N3 C8 H8 126.4 . . ?
C9 C8 N3 107.2(4) . . ?
C9 C8 H8 126.4 . . ?
N4 C9 H9 126.4 . . ?
C8 C9 N4 107.1(4) . . ?
C8 C9 H9 126.4 . . ?
N3 C10 H10A 109.3 . . ?
N3 C10 H10B 109.3 . . ?
N3 C10 C11 111.4(4) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N4 C12 H12A 109.5 . . ?
N4 C12 H12B 109.5 . . ?
N4 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Cl2 Y1 Cl1 88.06(4) . . ?
Cl2 Y1 Cl3 92.62(4) . . ?
Cl2 Y1 Cl4 178.15(6) . . ?
Cl2 Y1 Cl5 90.36(4) . . ?
Cl2 Y1 Cl6 93.44(4) . . ?
Cl3 Y1 Cl1 177.99(5) . . ?
Cl3 Y1 Cl4 89.17(4) . . ?
Cl3 Y1 Cl5 88.88(4) . . ?
Cl3 Y1 Cl6 92.71(4) . . ?
Cl4 Y1 Cl1 90.16(3) . . ?
Cl4 Y1 Cl5 90.14(4) . . ?
Cl4 Y1 Cl6 86.01(4) . . ?
Cl5 Y1 Cl1 89.23(4) . . ?
Cl5 Y1 Cl6 175.82(5) . . ?
Cl6 Y1 Cl1 89.14(4) . . ?
C1 N1 C2 108.1(4) . . ?
C1 N1 C4 125.9(4) . . ?
C2 N1 C4 126.0(4) . . ?
C1 N2 C3 108.5(4) . . ?
C1 N2 C6 125.6(4) . . ?
C3 N2 C6 125.7(4) . . ?
C13 N5 C14 107.5(4) . . ?
C13 N5 C16 125.8(4) . . ?
C14 N5 C16 126.7(4) . . ?
C13 N6 C15 108.1(5) . . ?
C13 N6 C18 127.6(5) . . ?
C15 N6 C18 124.2(4) . . ?
N1 C1 H1 125.8 . . ?
N2 C1 N1 108.4(4) . . ?
N2 C1 H1 125.8 . . ?
N2 C3 H3 126.5 . . ?
C2 C3 N2 107.0(4) . . ?
C2 C3 H3 126.5 . . ?
N1 C2 H2 126.0 . . ?
C3 C2 N1 108.0(5) . . ?
C3 C2 H2 126.0 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 C5 110.9(4) . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N5 C13 H13 125.3 . . ?
N6 C13 N5 109.4(4) . . ?
N6 C13 H13 125.3 . . ?
N5 C14 H14 126.1 . . ?
C15 C14 N5 107.9(5) . . ?
C15 C14 H14 126.1 . . ?
N6 C15 H15 126.5 . . ?
C14 C15 N6 107.1(4) . . ?
C14 C15 H15 126.5 . . ?
N5 C16 H16A 109.5 . . ?
N5 C16 H16B 109.5 . . ?
N5 C16 C17 110.9(4) . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N6 C18 H18A 109.5 . . ?
N6 C18 H18B 109.5 . . ?
N6 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
C7 H7 Cl1 0.95 2.77 3.588(5) 145.0 2_664
C7 H7 Cl2 0.95 2.92 3.650(4) 134.6 2_664
C8 H8 Cl4 0.95 2.82 3.695(4) 153.1 3_544
C9 H9 Cl2 0.95 2.86 3.604(5) 135.8 1_545
C9 H9 Cl6 0.95 2.79 3.459(4) 128.6 1_545
C1 H1 Cl6 0.95 2.71 3.547(4) 146.6 .
C3 H3 Cl1 0.95 2.66 3.584(5) 165.0 2_664
C13 H13 Cl3 0.95 2.84 3.531(5) 130.0 1_554
C13 H13 Cl5 0.95 2.68 3.422(5) 135.9 1_554
C15 H15 Cl3 0.95 2.61 3.365(5) 136.2 3_544

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C8 C9 N4 0.6(5) . . . . ?
C7 N3 C8 C9 -1.0(5) . . . . ?
C7 N3 C10 C11 113.0(5) . . . . ?
C7 N4 C9 C8 0.1(5) . . . . ?
C8 N3 C7 N4 1.0(5) . . . . ?
C8 N3 C10 C11 -65.6(6) . . . . ?
C9 N4 C7 N3 -0.7(5) . . . . ?
C10 N3 C7 N4 -177.7(4) . . . . ?
C10 N3 C8 C9 177.8(4) . . . . ?
C12 N4 C7 N3 179.8(4) . . . . ?
C12 N4 C9 C8 179.5(4) . . . . ?
N2 C3 C2 N1 0.5(5) . . . . ?
N5 C14 C15 N6 -1.3(5) . . . . ?
C1 N1 C2 C3 -0.4(5) . . . . ?
C1 N1 C4 C5 118.8(5) . . . . ?
C1 N2 C3 C2 -0.5(5) . . . . ?
C3 N2 C1 N1 0.3(5) . . . . ?
C2 N1 C1 N2 0.1(5) . . . . ?
C2 N1 C4 C5 -58.7(6) . . . . ?
C4 N1 C1 N2 -177.8(4) . . . . ?
C4 N1 C2 C3 177.5(4) . . . . ?
C6 N2 C1 N1 -175.0(4) . . . . ?
C6 N2 C3 C2 174.8(4) . . . . ?
C13 N5 C14 C15 1.3(5) . . . . ?
C13 N5 C16 C17 109.9(5) . . . . ?
C13 N6 C15 C14 0.8(5) . . . . ?
C14 N5 C13 N6 -0.8(5) . . . . ?
C14 N5 C16 C17 -70.4(6) . . . . ?
C15 N6 C13 N5 0.0(5) . . . . ?
C16 N5 C13 N6 178.9(4) . . . . ?
C16 N5 C14 C15 -178.4(4) . . . . ?
C18 N6 C13 N5 -177.4(4) . . . . ?
C18 N6 C15 C14 178.3(4) . . . . ?

####################################################################### 
# 
# 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_2012kmjdc17a1x
_database_code_depnum_ccdc_archive 'CCDC 1472566'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2016-06-20 downloaded from the CCDC.
;
_audit_creation_date             2014-05-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '3(C6 H11 N2), Ce Cl6'
_chemical_formula_sum            'C18 H33 Ce Cl6 N6'
_chemical_formula_weight         686.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Ce Ce -0.2486 2.6331 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.492(3)
_cell_length_b                   12.549(2)
_cell_length_c                   14.708(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.482(3)
_cell_angle_gamma                90
_cell_volume                     2859.2(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6063
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.5
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.170
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plank
_exptl_crystal_F_000             1372
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1212
_diffrn_reflns_av_unetI/netI     0.0989
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13077
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.517
_diffrn_reflns_theta_min         2.500
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.011993
_diffrn_orient_matrix_UB_12      -0.031827
_diffrn_orient_matrix_UB_13      0.058876
_diffrn_orient_matrix_UB_21      -0.077495
_diffrn_orient_matrix_UB_22      0.017448
_diffrn_orient_matrix_UB_23      -0.006354
_diffrn_orient_matrix_UB_31      -0.009924
_diffrn_orient_matrix_UB_32      -0.055515
_diffrn_orient_matrix_UB_33      -0.031406
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           55.0
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4210
_reflns_number_total             6491
_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.

All the crystals of [EMIM]3[CeCl6] looked at in this study 
were multiply twinned, thus explaining the relatively high 
Rint value, although the twinned components were very minor 
contributors to the overall dataset. This caused a couple of 
large Q-peaks to appear close to the cerium atoms 
(3.2 e/Å³ at ∼1.04 Å distance from Ce) as well as 
two large holes (-5.9 e/Å³ at ∼0.84 Å). Attempts 
to reprocess the dataset did not result in any improvement 
in the Rint value, nor were the Q-peaks or holes affected, 
and recollection was not possible. This explains the level A 
and B CheckCIF errors PLAT971_ALERT_2_A and PLAT971_ALERT_2_B.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         3.212
_refine_diff_density_min         -5.344
_refine_diff_density_rms         0.251
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         6491
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0644
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1684
_refine_ls_wR_factor_ref         0.1867
_refine_special_details          
;
All the crystals looked at in this study were multiply twinned. All attempts 
at multi-component twin integration failed. A satisfactory dataset was 
obtained by integrating on just the major component and ignoring the minor 
overlaps from the other domains. This caused a couple of large Q-peaks to 
appear close to the cerium atoms (3.2 eÅ³ at ca. 1.04 Å distance from 
Ce) as well as two large holes (--5.9 eÅ³ at ca. 0.84 Å from Ce). This 
explains the level A and B CheckCIF errors PLAT971_ALERT_2_A (holes) and 
PLAT971_ALERT_2_B (Q-peaks). 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C16(H16A,H16B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C15(H15), C2(H2), C3(H3), C1(H1), C14(H14), C7(H7), C8(H8), C9(H9)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C5(H5A,H5B,H5C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C),
 C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ce1 Ce 0.0000 0.0000 0.0000 0.01345(15) Uani 1 2 d S T P . .
Ce2 Ce -0.5000 0.0000 0.5000 0.01429(15) Uani 1 2 d S T P . .
Cl4 Cl -0.33596(10) 0.03442(14) 0.57141(11) 0.0204(3) Uani 1 1 d . . . . .
Cl1 Cl -0.03519(10) -0.18314(13) 0.10029(10) 0.0190(3) Uani 1 1 d . . . . .
Cl5 Cl -0.49203(10) -0.21305(13) 0.54996(11) 0.0220(4) Uani 1 1 d . . . . .
Cl3 Cl -0.00440(11) 0.12392(13) 0.15606(11) 0.0219(4) Uani 1 1 d . . . . .
Cl2 Cl 0.17584(11) -0.02158(15) 0.02030(14) 0.0271(4) Uani 1 1 d . . . . .
Cl6 Cl -0.56963(10) 0.04416(15) 0.66888(11) 0.0247(4) Uani 1 1 d . . . . .
N2 N -0.1819(4) -0.1366(4) 0.4161(4) 0.0185(12) Uani 1 1 d . . . . .
C6 C -0.2435(4) -0.1983(6) 0.4708(5) 0.0249(15) Uani 1 1 d . . . . .
H6A H -0.2561 -0.1601 0.5257 0.037 Uiso 1 1 calc GR . . . .
H6B H -0.2188 -0.2663 0.4859 0.037 Uiso 1 1 calc GR . . . .
H6C H -0.2958 -0.2088 0.4366 0.037 Uiso 1 1 calc GR . . . .
C4 C 0.0307(4) -0.0808(5) 0.3317(4) 0.0176(13) Uani 1 1 d . . . . .
H4A H 0.0367 -0.0654 0.2675 0.021 Uiso 1 1 calc R . . . .
H4B H 0.0583 -0.1488 0.3438 0.021 Uiso 1 1 calc R . . . .
C13 C -0.2961(5) 0.2105(6) 0.3572(6) 0.0292(17) Uani 1 1 d . . . . .
H13 H -0.3384 0.1819 0.3945 0.035 Uiso 1 1 calc R . . . .
N1 N -0.0621(3) -0.0882(4) 0.3542(4) 0.0179(11) Uani 1 1 d . . . . .
N5 N -0.3088(4) 0.2407(5) 0.2731(5) 0.0281(14) Uani 1 1 d . . . . .
C15 C -0.1735(5) 0.2686(7) 0.3083(5) 0.0328(18) Uani 1 1 d . . . . .
H15 H -0.1156 0.2877 0.3063 0.039 Uiso 1 1 calc R . . . .
C2 C -0.1269(4) -0.0220(6) 0.3197(5) 0.0205(14) Uani 1 1 d . . . . .
H2 H -0.1204 0.0327 0.2777 0.025 Uiso 1 1 calc R . . . .
C3 C -0.2016(4) -0.0533(6) 0.3597(5) 0.0208(14) Uani 1 1 d . . . . .
H3 H -0.2559 -0.0235 0.3504 0.025 Uiso 1 1 calc R . . . .
C1 C -0.0979(4) -0.1570(5) 0.4122(4) 0.0186(13) Uani 1 1 d . . . . .
H1 H -0.0689 -0.2101 0.4443 0.022 Uiso 1 1 calc R . . . .
N6 N -0.2149(4) 0.2260(5) 0.3820(4) 0.0241(13) Uani 1 1 d . . . . .
C5 C 0.0756(5) 0.0056(5) 0.3869(6) 0.0252(16) Uani 1 1 d . . . . .
H5A H 0.0516 0.0737 0.3713 0.038 Uiso 1 1 calc GR . . . .
H5B H 0.1362 0.0053 0.3736 0.038 Uiso 1 1 calc GR . . . .
H5C H 0.0675 -0.0077 0.4505 0.038 Uiso 1 1 calc GR . . . .
C17 C -0.3761(6) 0.1591(7) 0.1364(6) 0.045(2) Uani 1 1 d . . . . .
H17A H -0.3614 0.0887 0.1567 0.068 Uiso 1 1 calc GR . . . .
H17B H -0.3303 0.1869 0.0998 0.068 Uiso 1 1 calc GR . . . .
H17C H -0.4284 0.1563 0.1009 0.068 Uiso 1 1 calc GR . . . .
C18 C -0.1745(5) 0.2021(6) 0.4698(5) 0.0287(17) Uani 1 1 d . . . . .
H18A H -0.1728 0.2655 0.5063 0.043 Uiso 1 1 calc GR . . . .
H18B H -0.1168 0.1768 0.4604 0.043 Uiso 1 1 calc GR . . . .
H18C H -0.2074 0.1483 0.5004 0.043 Uiso 1 1 calc GR . . . .
C16 C -0.3892(5) 0.2298(8) 0.2169(6) 0.042(2) Uani 1 1 d . . . . .
H16A H -0.4073 0.2998 0.1962 0.050 Uiso 1 1 calc R . . . .
H16B H -0.4348 0.2008 0.2542 0.050 Uiso 1 1 calc R . . . .
C14 C -0.2305(5) 0.2779(8) 0.2397(5) 0.037(2) Uani 1 1 d . . . . .
H14 H -0.2199 0.3040 0.1816 0.044 Uiso 1 1 calc R . . . .
N4 N -0.2840(3) -0.2446(5) 0.2028(4) 0.0206(12) Uani 1 1 d . . . . .
C7 C -0.3485(4) -0.3072(6) 0.2277(5) 0.0259(16) Uani 1 1 d . . . . .
H7 H -0.4062 -0.2963 0.2125 0.031 Uiso 1 1 calc R . . . .
N3 N -0.3190(4) -0.3875(5) 0.2771(4) 0.0233(13) Uani 1 1 d . . . . .
C8 C -0.2306(4) -0.3764(6) 0.2833(5) 0.0243(15) Uani 1 1 d . . . . .
H8 H -0.1930 -0.4221 0.3137 0.029 Uiso 1 1 calc R . . . .
C9 C -0.2085(5) -0.2888(6) 0.2381(5) 0.0256(16) Uani 1 1 d . . . . .
H9 H -0.1529 -0.2620 0.2314 0.031 Uiso 1 1 calc R . . . .
C12 C -0.2930(5) -0.1461(6) 0.1502(5) 0.0303(17) Uani 1 1 d . . . . .
H12A H -0.3376 -0.1548 0.1051 0.045 Uiso 1 1 calc GR . . . .
H12B H -0.2394 -0.1302 0.1209 0.045 Uiso 1 1 calc GR . . . .
H12C H -0.3080 -0.0886 0.1902 0.045 Uiso 1 1 calc GR . . . .
C10 C -0.3712(6) -0.4753(7) 0.3147(6) 0.036(2) Uani 1 1 d . . . . .
H10A H -0.3387 -0.5412 0.3103 0.044 Uiso 1 1 calc R . . . .
H10B H -0.4232 -0.4833 0.2780 0.044 Uiso 1 1 calc R . . . .
C11 C -0.3964(5) -0.4582(7) 0.4124(5) 0.0317(18) Uani 1 1 d . . . . .
H11A H -0.4250 -0.3907 0.4181 0.048 Uiso 1 1 calc GR . . . .
H11B H -0.3456 -0.4588 0.4502 0.048 Uiso 1 1 calc GR . . . .
H11C H -0.4347 -0.5141 0.4310 0.048 Uiso 1 1 calc GR . . . .


_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
Ce1 Cl1 2.7872(16) . ?
Ce1 Cl1 2.7871(16) 3 ?
Ce1 Cl3 2.7738(16) 3 ?
Ce1 Cl3 2.7738(16) . ?
Ce1 Cl2 2.7514(17) 3 ?
Ce1 Cl2 2.7514(17) . ?
Ce2 Cl4 2.7756(15) 3_456 ?
Ce2 Cl4 2.7755(15) . ?
Ce2 Cl5 2.7752(17) . ?
Ce2 Cl5 2.7752(17) 3_456 ?
Ce2 Cl6 2.7722(17) . ?
Ce2 Cl6 2.7722(17) 3_456 ?
N2 C6 1.474(8) . ?
N2 C3 1.369(8) . ?
N2 C1 1.327(8) . ?
C4 N1 1.481(8) . ?
C4 C5 1.519(9) . ?
C13 N5 1.307(10) . ?
C13 N6 1.321(9) . ?
N1 C2 1.396(8) . ?
N1 C1 1.337(9) . ?
N5 C16 1.495(9) . ?
N5 C14 1.394(9) . ?
C15 N6 1.373(9) . ?
C15 C14 1.340(10) . ?
C2 C3 1.360(9) . ?
N6 C18 1.461(9) . ?
C17 C16 1.495(13) . ?
N4 C7 1.325(9) . ?
N4 C9 1.392(9) . ?
N4 C12 1.464(9) . ?
C7 N3 1.322(9) . ?
N3 C8 1.378(8) . ?
N3 C10 1.478(10) . ?
C8 C9 1.331(11) . ?
C10 C11 1.508(11) . ?

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
Cl1 Ce1 Cl1 180.0 3 . ?
Cl3 Ce1 Cl1 91.04(5) . . ?
Cl3 Ce1 Cl1 91.04(5) 3 3 ?
Cl3 Ce1 Cl1 88.96(5) 3 . ?
Cl3 Ce1 Cl1 88.96(5) . 3 ?
Cl3 Ce1 Cl3 180.0 3 . ?
Cl2 Ce1 Cl1 93.40(5) . . ?
Cl2 Ce1 Cl1 86.60(5) . 3 ?
Cl2 Ce1 Cl1 93.40(5) 3 3 ?
Cl2 Ce1 Cl1 86.60(5) 3 . ?
Cl2 Ce1 Cl3 90.19(5) . 3 ?
Cl2 Ce1 Cl3 89.81(5) . . ?
Cl2 Ce1 Cl3 89.81(5) 3 3 ?
Cl2 Ce1 Cl3 90.19(5) 3 . ?
Cl2 Ce1 Cl2 180.0 . 3 ?
Cl4 Ce2 Cl4 180.0 . 3_456 ?
Cl5 Ce2 Cl4 90.64(5) 3_456 3_456 ?
Cl5 Ce2 Cl4 89.36(5) . 3_456 ?
Cl5 Ce2 Cl4 89.36(5) 3_456 . ?
Cl5 Ce2 Cl4 90.64(5) . . ?
Cl5 Ce2 Cl5 180.0 3_456 . ?
Cl6 Ce2 Cl4 89.53(5) 3_456 3_456 ?
Cl6 Ce2 Cl4 90.47(5) . 3_456 ?
Cl6 Ce2 Cl4 89.53(5) . . ?
Cl6 Ce2 Cl4 90.47(5) 3_456 . ?
Cl6 Ce2 Cl5 88.40(5) . . ?
Cl6 Ce2 Cl5 91.60(5) 3_456 . ?
Cl6 Ce2 Cl5 88.40(5) 3_456 3_456 ?
Cl6 Ce2 Cl5 91.60(5) . 3_456 ?
Cl6 Ce2 Cl6 180.0 3_456 . ?
C3 N2 C6 126.2(6) . . ?
C1 N2 C6 124.2(6) . . ?
C1 N2 C3 109.5(5) . . ?
N1 C4 C5 111.5(5) . . ?
N5 C13 N6 110.8(7) . . ?
C2 N1 C4 125.4(6) . . ?
C1 N1 C4 126.3(5) . . ?
C1 N1 C2 108.3(6) . . ?
C13 N5 C16 128.0(7) . . ?
C13 N5 C14 107.8(6) . . ?
C14 N5 C16 124.0(7) . . ?
C14 C15 N6 108.7(7) . . ?
C3 C2 N1 106.4(6) . . ?
C2 C3 N2 107.3(6) . . ?
N2 C1 N1 108.4(5) . . ?
C13 N6 C15 106.8(6) . . ?
C13 N6 C18 127.9(6) . . ?
C15 N6 C18 125.3(6) . . ?
N5 C16 C17 112.0(7) . . ?
C15 C14 N5 106.0(7) . . ?
C7 N4 C9 107.1(6) . . ?
C7 N4 C12 125.3(6) . . ?
C9 N4 C12 127.6(6) . . ?
N3 C7 N4 110.2(6) . . ?
C7 N3 C8 107.4(6) . . ?
C7 N3 C10 125.9(6) . . ?
C8 N3 C10 126.7(6) . . ?
C9 C8 N3 108.1(6) . . ?
C8 C9 N4 107.3(6) . . ?
N3 C10 C11 113.3(7) . . ?

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
C13 H13 Cl5 0.93 2.79 3.566(8) 142.2 3_456
C15 H15 Cl1 0.93 2.72 3.544(8) 147.4 2
C2 H2 Cl3 0.93 2.79 3.581(7) 143.4 .
C3 H3 Cl6 0.93 2.73 3.567(7) 150.7 3_456
C1 H1 Cl1 0.93 2.70 3.547(6) 151.0 4_556
C1 H1 Cl3 0.93 2.80 3.333(7) 117.5 2_545
C7 H7 Cl5 0.93 2.73 3.427(7) 132.6 4
C8 H8 Cl2 0.93 2.75 3.513(7) 139.6 2_545
C9 H9 Cl1 0.93 2.84 3.629(8) 142.8 .

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1472567'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2016-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H33 N6, Br6 La'
_chemical_formula_sum            'C18 H33 Br6 La N6'
_chemical_formula_weight         951.87

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'
Br Br -0.2901 2.4595 '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                   15.925(5)
_cell_length_b                   12.787(4)
_cell_length_c                   15.252(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.588(5)
_cell_angle_gamma                90
_cell_volume                     3105.8(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9207
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      27.5

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.036
_exptl_crystal_F_000             1800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    9.111
_shelx_estimated_absorpt_T_min   0.611
_shelx_estimated_absorpt_T_max   0.839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.627
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Mitegen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            14407
_diffrn_reflns_av_unetI/netI     0.1324
_diffrn_reflns_av_R_equivalents  0.0919
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.950
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6318
_reflns_number_gt                4645
_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       
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;

_computing_structure_solution    'SUPERFLIP (Palatinus and Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-III (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2003), WinGX (Farrugia, 1999) and enCIFer (Allen et al., 2004).'

_refine_special_details          
;
All the crystals looked at in this study were multiply twinned. All attempts 
at multi-component twin integration failed. A satisfactory dataset was 
obtained by integrating on just the major component and ignoring the minor 
overlaps from the other domains. This caused a couple of large Q-peaks to 
appear close to the cerium atoms (3.2 eÅ³ at ca. 1.04 Å distance from 
La) as well as two large holes (--5.9 eÅ³ at ca. 0.84 Å from La). This 
explains the level A and B CheckCIF errors PLAT971_ALERT_2_A (holes) and 
PLAT971_ALERT_2_B (Q-peaks). 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0380P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6318
_refine_ls_number_parameters     289
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1156
_refine_ls_R_factor_gt           0.0818
_refine_ls_wR_factor_ref         0.1475
_refine_ls_wR_factor_gt          0.1337
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.147
_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
C1 C 0.6508(8) 0.3144(10) 0.2299(7) 0.034(3) Uani 1 1 d . . . . .
H1 H 0.5935 0.3023 0.2155 0.040 Uiso 1 1 calc R U . . .
C2 C 0.7671(8) 0.3826(10) 0.2862(7) 0.033(3) Uani 1 1 d . . . . .
H2 H 0.8042 0.4269 0.3183 0.039 Uiso 1 1 calc R U . . .
C3 C 0.7895(7) 0.2985(9) 0.2380(6) 0.026(3) Uani 1 1 d . . . . .
H3 H 0.8447 0.2725 0.2291 0.032 Uiso 1 1 calc R U . . .
C4 C 0.6277(9) 0.4793(12) 0.3178(8) 0.053(4) Uani 1 1 d . . . . .
H4A H 0.6606 0.5450 0.3196 0.063 Uiso 1 1 calc R U . . .
H4B H 0.5778 0.4908 0.2797 0.063 Uiso 1 1 calc R U . . .
C5 C 0.6001(9) 0.4519(11) 0.4083(8) 0.051(4) Uani 1 1 d . . . . .
H5A H 0.5681 0.3865 0.4066 0.077 Uiso 1 1 calc R U . . .
H5B H 0.5646 0.5080 0.4312 0.077 Uiso 1 1 calc R U . . .
H5C H 0.6494 0.4433 0.4465 0.077 Uiso 1 1 calc R U . . .
C6 C 0.7093(7) 0.1625(9) 0.1499(7) 0.028(3) Uani 1 1 d . . . . .
H6A H 0.7659 0.1411 0.1329 0.042 Uiso 1 1 calc R U . . .
H6B H 0.6755 0.1766 0.0972 0.042 Uiso 1 1 calc R U . . .
H6C H 0.6831 0.1064 0.1838 0.042 Uiso 1 1 calc R U . . .
C7 C 0.9048(7) 0.1552(8) 0.4123(6) 0.023(3) Uani 1 1 d . . . . .
H7 H 0.9343 0.2039 0.4482 0.028 Uiso 1 1 calc R U . . .
C8 C 0.8769(8) 0.0343(9) 0.3149(7) 0.029(3) Uani 1 1 d . . . . .
H8 H 0.8840 -0.0173 0.2708 0.035 Uiso 1 1 calc R U . . .
C9 C 0.8013(8) 0.0654(9) 0.3503(6) 0.028(3) Uani 1 1 d . . . . .
H9 H 0.7467 0.0407 0.3357 0.033 Uiso 1 1 calc R U . . .
C10 C 1.0304(7) 0.0825(9) 0.3349(6) 0.023(3) Uani 1 1 d . . . . .
H10A H 1.0577 0.1506 0.3472 0.028 Uiso 1 1 calc R U . . .
H10B H 1.0378 0.0665 0.2719 0.028 Uiso 1 1 calc R U . . .
C11 C 1.0717(8) -0.0011(9) 0.3892(7) 0.034(3) Uani 1 1 d . . . . .
H11A H 1.0458 -0.0689 0.3758 0.051 Uiso 1 1 calc R U . . .
H11B H 1.0646 0.0148 0.4516 0.051 Uiso 1 1 calc R U . . .
H11C H 1.1317 -0.0039 0.3757 0.051 Uiso 1 1 calc R U . . .
C12 C 0.7641(8) 0.1987(9) 0.4647(7) 0.035(3) Uani 1 1 d . . . . .
H12A H 0.7597 0.1657 0.5224 0.052 Uiso 1 1 calc R U . . .
H12B H 0.7088 0.1995 0.4360 0.052 Uiso 1 1 calc R U . . .
H12C H 0.7845 0.2706 0.4716 0.052 Uiso 1 1 calc R U . . .
C13 C 0.2884(11) 0.1990(11) -0.3427(9) 0.051(4) Uani 1 1 d . . . . .
H13 H 0.3284 0.1652 -0.3788 0.061 Uiso 1 1 calc R U . . .
C14 C 0.2325(11) 0.2688(14) -0.2348(10) 0.075(5) Uani 1 1 d . U . . .
H14 H 0.2238 0.2968 -0.1779 0.089 Uiso 1 1 calc R U . . .
C15 C 0.1757(10) 0.2602(12) -0.2969(8) 0.056(4) Uani 1 1 d . U . . .
H15 H 0.1185 0.2810 -0.2937 0.068 Uiso 1 1 calc R U . . .
C16 C 0.3827(11) 0.2239(13) -0.2130(11) 0.069(5) Uani 1 1 d . . . . .
H16A H 0.3987 0.2946 -0.1923 0.083 Uiso 1 1 calc R U . . .
H16B H 0.4290 0.1967 -0.2494 0.083 Uiso 1 1 calc R U . . .
C17 C 0.3700(10) 0.1514(13) -0.1334(9) 0.074(5) Uani 1 1 d . . . . .
H17A H 0.3159 0.1668 -0.1063 0.111 Uiso 1 1 calc R U . . .
H17B H 0.4154 0.1629 -0.0905 0.111 Uiso 1 1 calc R U . . .
H17C H 0.3708 0.0783 -0.1528 0.111 Uiso 1 1 calc R U . . .
C18 C 0.1744(10) 0.1890(11) -0.4541(8) 0.062(5) Uani 1 1 d . . . . .
H18A H 0.1754 0.2505 -0.4924 0.093 Uiso 1 1 calc R U . . .
H18B H 0.1161 0.1672 -0.4450 0.093 Uiso 1 1 calc R U . . .
H18C H 0.2056 0.1318 -0.4815 0.093 Uiso 1 1 calc R U . . .
N1 N 0.6805(7) 0.3929(8) 0.2805(5) 0.036(3) Uani 1 1 d . . . . .
N2 N 0.7144(7) 0.2579(8) 0.2038(5) 0.029(2) Uani 1 1 d . . . . .
N3 N 0.9391(6) 0.0903(7) 0.3542(5) 0.021(2) Uani 1 1 d . . . . .
N4 N 0.8226(6) 0.1398(7) 0.4112(5) 0.024(2) Uani 1 1 d . . . . .
N5 N 0.3062(8) 0.2307(9) -0.2660(8) 0.050(3) Uani 1 1 d . . . . .
N6 N 0.2143(8) 0.2156(9) -0.3675(8) 0.053(3) Uani 1 1 d . . . . .
Br1 Br 0.99601(8) 0.37572(9) 0.33806(6) 0.0252(3) Uani 1 1 d . . . . .
Br2 Br 0.81757(8) 0.52738(11) 0.48874(8) 0.0387(3) Uani 1 1 d . . . . .
Br3 Br 1.03414(8) 0.68967(9) 0.39577(7) 0.0285(3) Uani 1 1 d . . . . .
Br4 Br 0.50191(8) 0.27904(9) 0.05506(7) 0.0294(3) Uani 1 1 d . . . . .
Br5 Br 0.66998(7) 0.52969(9) 0.07433(7) 0.0269(3) Uani 1 1 d . . . . .
Br6 Br 0.42967(8) 0.55614(10) 0.17206(7) 0.0304(3) Uani 1 1 d . . . . .
La1 La 1.0000 0.5000 0.5000 0.0201(2) Uani 1 2 d S . P . .
La2 La 0.5000 0.5000 0.0000 0.0208(2) Uani 1 2 d S . P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.309(15) . ?
C1 N1 1.348(14) . ?
C1 H1 0.9500 . ?
C2 C3 1.353(15) . ?
C2 N1 1.387(15) . ?
C2 H2 0.9500 . ?
C3 N2 1.400(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.495(16) . ?
C4 N1 1.505(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 N2 1.473(13) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 N4 1.325(13) . ?
C7 N3 1.335(13) . ?
C7 H7 0.9500 . ?
C8 N3 1.357(13) . ?
C8 C9 1.383(16) . ?
C8 H8 0.9500 . ?
C9 N4 1.370(13) . ?
C9 H9 0.9500 . ?
C10 N3 1.489(13) . ?
C10 C11 1.501(14) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N4 1.453(13) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N6 1.254(17) . ?
C13 N5 1.268(15) . ?
C13 H13 0.9500 . ?
C14 C15 1.307(19) . ?
C14 N5 1.361(18) . ?
C14 H14 0.9500 . ?
C15 N6 1.370(16) . ?
C15 H15 0.9500 . ?
C16 N5 1.458(18) . ?
C16 C17 1.54(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N6 1.499(16) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
Br1 La1 2.9371(13) . ?
Br2 La1 2.9296(16) . ?
Br3 La1 2.9534(13) . ?
Br4 La2 2.9477(15) . ?
Br5 La2 2.9486(14) . ?
Br6 La2 2.9524(13) . ?
La1 Br2 2.9296(16) 3_766 ?
La1 Br1 2.9371(13) 3_766 ?
La1 Br3 2.9534(13) 3_766 ?
La2 Br4 2.9476(15) 3_665 ?
La2 Br5 2.9486(14) 3_665 ?
La2 Br6 2.9524(13) 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
N2 C1 N1 108.5(12) . . ?
N2 C1 H1 125.7 . . ?
N1 C1 H1 125.7 . . ?
C3 C2 N1 108.0(10) . . ?
C3 C2 H2 126.0 . . ?
N1 C2 H2 126.0 . . ?
C2 C3 N2 105.5(11) . . ?
C2 C3 H3 127.2 . . ?
N2 C3 H3 127.2 . . ?
C5 C4 N1 110.4(11) . . ?
C5 C4 H4A 109.6 . . ?
N1 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
N1 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C7 N3 108.1(10) . . ?
N4 C7 H7 125.9 . . ?
N3 C7 H7 125.9 . . ?
N3 C8 C9 108.1(10) . . ?
N3 C8 H8 126.0 . . ?
C9 C8 H8 126.0 . . ?
N4 C9 C8 104.8(10) . . ?
N4 C9 H9 127.6 . . ?
C8 C9 H9 127.6 . . ?
N3 C10 C11 111.2(9) . . ?
N3 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
N3 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N4 C12 H12A 109.5 . . ?
N4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N6 C13 N5 115.1(15) . . ?
N6 C13 H13 122.4 . . ?
N5 C13 H13 122.4 . . ?
C15 C14 N5 108.1(14) . . ?
C15 C14 H14 126.0 . . ?
N5 C14 H14 126.0 . . ?
C14 C15 N6 107.0(14) . . ?
C14 C15 H15 126.5 . . ?
N6 C15 H15 126.5 . . ?
N5 C16 C17 110.9(14) . . ?
N5 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
N5 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N6 C18 H18A 109.5 . . ?
N6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 N1 C2 107.9(11) . . ?
C1 N1 C4 124.7(12) . . ?
C2 N1 C4 127.2(11) . . ?
C1 N2 C3 110.0(10) . . ?
C1 N2 C6 126.1(11) . . ?
C3 N2 C6 123.9(10) . . ?
C7 N3 C8 108.6(10) . . ?
C7 N3 C10 125.4(9) . . ?
C8 N3 C10 126.0(9) . . ?
C7 N4 C9 110.4(9) . . ?
C7 N4 C12 123.7(10) . . ?
C9 N4 C12 125.8(10) . . ?
C13 N5 C14 104.6(14) . . ?
C13 N5 C16 132.0(14) . . ?
C14 N5 C16 123.2(13) . . ?
C13 N6 C15 105.2(13) . . ?
C13 N6 C18 128.1(13) . . ?
C15 N6 C18 126.7(13) . . ?
Br2 La1 Br2 180.0 . 3_766 ?
Br2 La1 Br1 89.86(3) . 3_766 ?
Br2 La1 Br1 90.14(3) 3_766 3_766 ?
Br2 La1 Br1 90.14(3) . . ?
Br2 La1 Br1 89.86(3) 3_766 . ?
Br1 La1 Br1 180.0 3_766 . ?
Br2 La1 Br3 86.66(4) . 3_766 ?
Br2 La1 Br3 93.34(4) 3_766 3_766 ?
Br1 La1 Br3 89.67(4) 3_766 3_766 ?
Br1 La1 Br3 90.33(4) . 3_766 ?
Br2 La1 Br3 93.34(4) . . ?
Br2 La1 Br3 86.66(4) 3_766 . ?
Br1 La1 Br3 90.33(4) 3_766 . ?
Br1 La1 Br3 89.67(4) . . ?
Br3 La1 Br3 180.0 3_766 . ?
Br4 La2 Br4 180.00(5) 3_665 . ?
Br4 La2 Br5 89.59(3) 3_665 . ?
Br4 La2 Br5 90.41(3) . . ?
Br4 La2 Br5 90.41(3) 3_665 3_665 ?
Br4 La2 Br5 89.59(3) . 3_665 ?
Br5 La2 Br5 180.0 . 3_665 ?
Br4 La2 Br6 89.01(4) 3_665 3_665 ?
Br4 La2 Br6 90.99(4) . 3_665 ?
Br5 La2 Br6 91.03(4) . 3_665 ?
Br5 La2 Br6 88.97(4) 3_665 3_665 ?
Br4 La2 Br6 90.99(4) 3_665 . ?
Br4 La2 Br6 89.01(4) . . ?
Br5 La2 Br6 88.97(4) . . ?
Br5 La2 Br6 91.03(4) 3_665 . ?
Br6 La2 Br6 180.0 3_665 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 -0.5(12) . . . . ?
N3 C8 C9 N4 -0.5(12) . . . . ?
N5 C14 C15 N6 0(2) . . . . ?
N2 C1 N1 C2 -0.6(12) . . . . ?
N2 C1 N1 C4 175.5(10) . . . . ?
C3 C2 N1 C1 0.7(12) . . . . ?
C3 C2 N1 C4 -175.2(10) . . . . ?
C5 C4 N1 C1 93.8(13) . . . . ?
C5 C4 N1 C2 -90.9(15) . . . . ?
N1 C1 N2 C3 0.3(12) . . . . ?
N1 C1 N2 C6 177.7(9) . . . . ?
C2 C3 N2 C1 0.2(12) . . . . ?
C2 C3 N2 C6 -177.4(9) . . . . ?
N4 C7 N3 C8 1.0(12) . . . . ?
N4 C7 N3 C10 179.9(9) . . . . ?
C9 C8 N3 C7 -0.2(12) . . . . ?
C9 C8 N3 C10 -179.2(9) . . . . ?
C11 C10 N3 C7 93.6(12) . . . . ?
C11 C10 N3 C8 -87.6(12) . . . . ?
N3 C7 N4 C9 -1.3(12) . . . . ?
N3 C7 N4 C12 -178.4(9) . . . . ?
C8 C9 N4 C7 1.2(12) . . . . ?
C8 C9 N4 C12 178.2(10) . . . . ?
N6 C13 N5 C14 3.2(19) . . . . ?
N6 C13 N5 C16 177.9(15) . . . . ?
C15 C14 N5 C13 -2.0(19) . . . . ?
C15 C14 N5 C16 -177.3(15) . . . . ?
C17 C16 N5 C13 -112.5(18) . . . . ?
C17 C16 N5 C14 61.4(19) . . . . ?
N5 C13 N6 C15 -2.9(19) . . . . ?
N5 C13 N6 C18 179.2(13) . . . . ?
C14 C15 N6 C13 1.4(19) . . . . ?
C14 C15 N6 C18 179.3(14) . . . . ?

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
C1 H1 Br4 0.95 2.85 3.579(12) 134.2 .
C2 H2 Br1 0.95 3.14 3.723(12) 121.6 .
C2 H2 Br2 0.95 2.91 3.683(11) 139.8 .
C3 H3 Br1 0.95 3.20 3.744(12) 118.3 .
C3 H3 Br3 0.95 2.92 3.755(11) 146.8 2_745
C7 H7 Br3 0.95 2.78 3.659(10) 153.8 3_766
C8 H8 Br1 0.95 2.89 3.708(12) 145.1 2_745
C9 H9 Br6 0.95 2.82 3.693(12) 153.7 2_645
C13 H13 Br4 0.95 3.04 3.765(17) 134.7 4_565
C15 H15 Br3 0.95 2.90 3.708(16) 143.9 3_665

_refine_diff_density_max         1.912
_refine_diff_density_min         -1.605
_refine_diff_density_rms         0.226

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_12mjdc14a1
_database_code_depnum_ccdc_archive 'CCDC 1472568'
_audit_update_record             
;
2016-04-06 deposited with the CCDC.
2016-06-20 downloaded from the CCDC.
;
_audit_creation_date             2014-05-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '3(C6 H11 N2), I6 La'
_chemical_formula_sum            'C18 H33 I6 La N6'
_chemical_formula_weight         1233.81
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.803(7)
_cell_length_b                   11.1325(15)
_cell_length_c                   17.017(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.162(7)
_cell_angle_gamma                90
_cell_volume                     3482.3(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    28995
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.1
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.439
_exptl_absorpt_coefficient_mu    6.562
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.221
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    2.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Prism
_exptl_crystal_F_000             2232
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            34033
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.441
_diffrn_reflns_theta_min         3.071
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 RX
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       
;
Crystal Goniometer
;
_diffrn_measurement_device_type  
;
Rigaku RAXIS conversion
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      0.008737
_diffrn_orient_matrix_UB_12      -0.087916
_diffrn_orient_matrix_UB_13      -0.006035
_diffrn_orient_matrix_UB_21      -0.027647
_diffrn_orient_matrix_UB_22      0.005637
_diffrn_orient_matrix_UB_23      -0.052376
_diffrn_orient_matrix_UB_31      0.052658
_diffrn_orient_matrix_UB_32      0.017547
_diffrn_orient_matrix_UB_33      -0.013414
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7104
_reflns_number_total             7929
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         2.183
_refine_diff_density_min         -1.011
_refine_diff_density_rms         0.205
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         7929
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0308
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0329P)²+6.1471P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0775
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C10(H10A,H10B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C),
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.59136(2) 1.39910(3) 0.37882(2) 0.01909(7) Uani 1 1 d . . . . .
I2 I 0.54505(2) 1.27618(2) 0.61219(2) 0.02088(8) Uani 1 1 d . . . . .
I3 I 0.35816(2) 1.36723(3) 0.40227(2) 0.02265(8) Uani 1 1 d . . . . .
I4 I 0.07001(2) 0.74068(2) 0.54520(2) 0.02211(8) Uani 1 1 d . . . . .
I5 I 0.02591(2) 1.06551(3) 0.68491(2) 0.02979(9) Uani 1 1 d . . . . .
I6 I 0.15823(2) 1.09840(3) 0.49915(2) 0.02489(8) Uani 1 1 d . . . . .
La1 La 0.5000 1.5000 0.5000 0.01361(8) Uani 1 2 d S T P . .
La2 La 0.0000 1.0000 0.5000 0.01521(8) Uani 1 2 d S T P . .
N1 N 0.4656(2) 0.9694(3) 0.6486(2) 0.0210(8) Uani 1 1 d . . . . .
N2 N 0.3846(2) 1.1105(3) 0.6328(2) 0.0217(8) Uani 1 1 d . . . . .
N3 N 0.2072(2) 0.8546(3) 0.7814(2) 0.0195(8) Uani 1 1 d . . . . .
N4 N 0.2240(2) 0.7563(3) 0.8933(2) 0.0206(8) Uani 1 1 d . . . . .
N5 N 0.1478(2) 1.4336(4) 0.6249(2) 0.0254(9) Uani 1 1 d . . . . .
N6 N 0.1506(2) 1.4353(3) 0.4988(3) 0.0254(9) Uani 1 1 d . . . . .
C1 C 0.4361(3) 1.0548(4) 0.6857(3) 0.0221(9) Uani 1 1 d . . . . .
H1 H 0.4497 1.0733 0.7414 0.027 Uiso 1 1 calc R . . . .
C2 C 0.4316(3) 0.9708(4) 0.5680(3) 0.0246(10) Uani 1 1 d . . . . .
H2 H 0.4413 0.9193 0.5270 0.029 Uiso 1 1 calc R . . . .
C3 C 0.3817(3) 1.0603(4) 0.5593(3) 0.0246(10) Uani 1 1 d . . . . .
H3 H 0.3502 1.0838 0.5105 0.029 Uiso 1 1 calc R . . . .
C4 C 0.5279(3) 0.8935(4) 0.6849(3) 0.0269(11) Uani 1 1 d . . . . .
H4A H 0.5212 0.8122 0.6610 0.032 Uiso 1 1 calc R . . . .
H4B H 0.5300 0.8858 0.7433 0.032 Uiso 1 1 calc R . . . .
C5 C 0.5987(3) 0.9463(4) 0.6717(3) 0.0262(10) Uani 1 1 d . . . . .
H5A H 0.5951 0.9606 0.6142 0.039 Uiso 1 1 calc GR . . . .
H5B H 0.6385 0.8900 0.6915 0.039 Uiso 1 1 calc GR . . . .
H5C H 0.6083 1.0224 0.7010 0.039 Uiso 1 1 calc GR . . . .
C6 C 0.3423(3) 1.2142(4) 0.6499(3) 0.0292(11) Uani 1 1 d . . . . .
H6A H 0.3414 1.2155 0.7073 0.044 Uiso 1 1 calc GR . . . .
H6B H 0.2924 1.2082 0.6183 0.044 Uiso 1 1 calc GR . . . .
H6C H 0.3647 1.2883 0.6356 0.044 Uiso 1 1 calc GR . . . .
C7 C 0.2538(3) 0.8344(4) 0.8505(3) 0.0212(9) Uani 1 1 d . . . . .
H7 H 0.3005 0.8699 0.8667 0.025 Uiso 1 1 calc R . . . .
C8 C 0.1459(3) 0.7868(5) 0.7794(3) 0.0292(11) Uani 1 1 d . . . . .
H8 H 0.1040 0.7839 0.7371 0.035 Uiso 1 1 calc R . . . .
C9 C 0.1565(3) 0.7250(5) 0.8492(3) 0.0286(11) Uani 1 1 d . . . . .
H9 H 0.1235 0.6700 0.8650 0.034 Uiso 1 1 calc R . . . .
C10 C 0.2248(3) 0.9275(4) 0.7161(3) 0.0277(11) Uani 1 1 d . . . . .
H10A H 0.2451 1.0056 0.7380 0.033 Uiso 1 1 calc R . . . .
H10B H 0.1797 0.9436 0.6756 0.033 Uiso 1 1 calc R . . . .
C11 C 0.2789(3) 0.8650(5) 0.6764(3) 0.0304(11) Uani 1 1 d . . . . .
H11A H 0.2607 0.7848 0.6588 0.046 Uiso 1 1 calc GR . . . .
H11B H 0.3255 0.8576 0.7149 0.046 Uiso 1 1 calc GR . . . .
H11C H 0.2858 0.9118 0.6298 0.046 Uiso 1 1 calc GR . . . .
C12 C 0.2577(3) 0.7100(5) 0.9730(3) 0.0291(11) Uani 1 1 d . . . . .
H12A H 0.3077 0.7398 0.9885 0.044 Uiso 1 1 calc GR . . . .
H12B H 0.2580 0.6220 0.9716 0.044 Uiso 1 1 calc GR . . . .
H12C H 0.2298 0.7372 1.0122 0.044 Uiso 1 1 calc GR . . . .
C13 C 0.1096(3) 1.4104(4) 0.5523(3) 0.0274(10) Uani 1 1 d . . . . .
H13 H 0.0611 1.3810 0.5399 0.033 Uiso 1 1 calc R . . . .
C14 C 0.2151(3) 1.4741(5) 0.6184(3) 0.0287(11) Uani 1 1 d . . . . .
H14 H 0.2532 1.4978 0.6617 0.034 Uiso 1 1 calc R . . . .
C15 C 0.2179(3) 1.4743(4) 0.5402(3) 0.0275(10) Uani 1 1 d . . . . .
H15 H 0.2581 1.4969 0.5177 0.033 Uiso 1 1 calc R . . . .
C16 C 0.1207(4) 1.4193(6) 0.6993(4) 0.0448(15) Uani 1 1 d . . . . .
H16A H 0.0721 1.3811 0.6864 0.054 Uiso 1 1 calc R . . . .
H16B H 0.1153 1.4995 0.7224 0.054 Uiso 1 1 calc R . . . .
C17 C 0.1708(5) 1.3439(10) 0.7607(4) 0.087(3) Uani 1 1 d . . . . .
H17A H 0.2188 1.3818 0.7742 0.130 Uiso 1 1 calc GR . . . .
H17B H 0.1753 1.2636 0.7386 0.130 Uiso 1 1 calc GR . . . .
H17C H 0.1508 1.3372 0.8093 0.130 Uiso 1 1 calc GR . . . .
C18 C 0.1275(4) 1.4258(5) 0.4110(3) 0.0391(13) Uani 1 1 d . . . . .
H18A H 0.1158 1.5059 0.3881 0.059 Uiso 1 1 calc GR . . . .
H18B H 0.0843 1.3744 0.3976 0.059 Uiso 1 1 calc GR . . . .
H18C H 0.1669 1.3907 0.3889 0.059 Uiso 1 1 calc GR . . . .


_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
I1 La1 3.1557(5) . ?
I2 La1 3.1448(4) . ?
I3 La1 3.1930(8) . ?
I4 La2 3.1988(5) . ?
I5 La2 3.1663(5) . ?
I6 La2 3.1733(10) . ?
La1 I1 3.1557(5) 3_686 ?
La1 I2 3.1448(4) 3_686 ?
La1 I3 3.1930(7) 3_686 ?
La2 I4 3.1988(5) 3_576 ?
La2 I5 3.1662(5) 3_576 ?
La2 I6 3.1734(10) 3_576 ?
N1 C1 1.326(6) . ?
N1 C2 1.387(6) . ?
N1 C4 1.470(6) . ?
N2 C1 1.329(6) . ?
N2 C3 1.360(6) . ?
N2 C6 1.467(6) . ?
N3 C7 1.329(6) . ?
N3 C8 1.373(6) . ?
N3 C10 1.469(6) . ?
N4 C7 1.331(6) . ?
N4 C9 1.377(6) . ?
N4 C12 1.464(6) . ?
N5 C13 1.317(7) . ?
N5 C14 1.369(7) . ?
N5 C16 1.469(7) . ?
N6 C13 1.341(7) . ?
N6 C15 1.381(7) . ?
N6 C18 1.468(7) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C2 C3 1.354(7) . ?
C3 H3 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.515(7) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.351(7) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.505(7) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.344(7) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.506(11) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I1 La1 I1 180.0 . 3_686 ?
I1 La1 I3 90.28(2) . . ?
I1 La1 I3 89.72(2) 3_686 . ?
I1 La1 I3 89.72(2) . 3_686 ?
I1 La1 I3 90.28(2) 3_686 3_686 ?
I2 La1 I1 89.964(11) 3_686 . ?
I2 La1 I1 90.036(12) 3_686 3_686 ?
I2 La1 I1 89.964(12) . 3_686 ?
I2 La1 I1 90.036(11) . . ?
I2 La1 I2 179.999(11) 3_686 . ?
I2 La1 I3 87.820(13) 3_686 . ?
I2 La1 I3 87.819(12) . 3_686 ?
I2 La1 I3 92.180(13) . . ?
I2 La1 I3 92.181(12) 3_686 3_686 ?
I3 La1 I3 180.0 3_686 . ?
I4 La2 I4 180.0 3_576 . ?
I5 La2 I4 89.975(10) 3_576 3_576 ?
I5 La2 I4 89.975(10) . . ?
I5 La2 I4 90.025(10) . 3_576 ?
I5 La2 I4 90.025(10) 3_576 . ?
I5 La2 I5 180.0 3_576 . ?
I5 La2 I6 91.322(11) 3_576 . ?
I5 La2 I6 91.323(11) . 3_576 ?
I5 La2 I6 88.677(11) 3_576 3_576 ?
I5 La2 I6 88.678(11) . . ?
I6 La2 I4 88.503(17) 3_576 3_576 ?
I6 La2 I4 91.497(16) . 3_576 ?
I6 La2 I4 91.497(17) 3_576 . ?
I6 La2 I4 88.503(16) . . ?
I6 La2 I6 180.0 . 3_576 ?
C1 N1 C2 108.1(4) . . ?
C1 N1 C4 126.0(4) . . ?
C2 N1 C4 125.7(4) . . ?
C1 N2 C3 108.3(4) . . ?
C1 N2 C6 125.5(4) . . ?
C3 N2 C6 126.0(4) . . ?
C7 N3 C8 108.8(4) . . ?
C7 N3 C10 123.4(4) . . ?
C8 N3 C10 127.4(4) . . ?
C7 N4 C9 108.2(4) . . ?
C7 N4 C12 126.0(4) . . ?
C9 N4 C12 125.8(4) . . ?
C13 N5 C14 108.7(4) . . ?
C13 N5 C16 124.5(5) . . ?
C14 N5 C16 126.8(5) . . ?
C13 N6 C15 108.3(4) . . ?
C13 N6 C18 125.9(5) . . ?
C15 N6 C18 125.8(4) . . ?
N1 C1 N2 109.3(4) . . ?
N1 C1 H1 125.4 . . ?
N2 C1 H1 125.4 . . ?
N1 C2 H2 126.8 . . ?
C3 C2 N1 106.4(4) . . ?
C3 C2 H2 126.8 . . ?
N2 C3 H3 126.0 . . ?
C2 C3 N2 108.0(4) . . ?
C2 C3 H3 126.0 . . ?
N1 C4 H4A 109.4 . . ?
N1 C4 H4B 109.4 . . ?
N1 C4 C5 111.2(4) . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C7 N4 108.7(4) . . ?
N3 C7 H7 125.7 . . ?
N4 C7 H7 125.7 . . ?
N3 C8 H8 126.5 . . ?
C9 C8 N3 106.9(4) . . ?
C9 C8 H8 126.5 . . ?
N4 C9 H9 126.3 . . ?
C8 C9 N4 107.4(4) . . ?
C8 C9 H9 126.3 . . ?
N3 C10 H10A 109.3 . . ?
N3 C10 H10B 109.3 . . ?
N3 C10 C11 111.4(4) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N4 C12 H12A 109.5 . . ?
N4 C12 H12B 109.5 . . ?
N4 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N5 C13 N6 108.6(4) . . ?
N5 C13 H13 125.7 . . ?
N6 C13 H13 125.7 . . ?
N5 C14 H14 126.0 . . ?
C15 C14 N5 108.0(4) . . ?
C15 C14 H14 126.0 . . ?
N6 C15 H15 126.8 . . ?
C14 C15 N6 106.4(4) . . ?
C14 C15 H15 126.8 . . ?
N5 C16 H16A 109.1 . . ?
N5 C16 H16B 109.1 . . ?
N5 C16 C17 112.3(6) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N6 C18 H18A 109.5 . . ?
N6 C18 H18B 109.5 . . ?
N6 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
C1 H1 I1 0.95 3.17 3.942(5) 139.8 4_586
C2 H2 I2 0.95 3.27 4.210(5) 172.5 3_676
C3 H3 I6 0.95 3.58 4.132(5) 119.7 .
C7 H7 I2 0.95 3.04 3.758(5) 134.0 2_646
C7 H7 I3 0.95 3.13 3.864(5) 134.9 4_586
C8 H8 I4 0.95 3.23 3.974(5) 136.7 .
C8 H8 I5 0.95 3.50 3.972(5) 113.5 .
C9 H9 I4 0.95 3.56 4.025(5) 112.5 4_576
C9 H9 I5 0.95 2.99 3.796(5) 143.2 2_546
C13 H13 I4 0.95 2.92 3.825(5) 160.4 3_576
C14 H14 I1 0.95 3.34 3.894(5) 119.0 3_686
C15 H15 I1 0.95 3.22 3.830(5) 124.0 3_686
C15 H15 I3 0.95 3.32 4.062(5) 136.1 .

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1472569'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2016-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '3(C7 H13 N2), Cl6 Y'
_chemical_formula_sum            'C21 H39 Cl6 N6 Y'
_chemical_formula_weight         677.19

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/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                   9.9170(8)
_cell_length_b                   16.2743(12)
_cell_length_c                   19.0282(16)
_cell_angle_alpha                90
_cell_angle_beta                 99.9730(10)
_cell_angle_gamma                90
_cell_volume                     3024.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9743
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.480
_shelx_estimated_absorpt_T_min   0.790
_shelx_estimated_absorpt_T_max   0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.675
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Sealed Tube'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            16980
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.012
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6878
_reflns_number_gt                5673
_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       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_structure_solution    'SUPERFLIP (Palatinus and Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-III (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2003), WinGX (Farrugia, 1999) and enCIFer (Allen et al., 2004).'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0339P)²+0.1609P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6878
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0674
_refine_ls_wR_factor_gt          0.0640
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
C1 C 0.44240(18) 0.91481(11) -0.06914(10) 0.0204(4) Uani 1 1 d . . . . .
C2 C 0.26528(18) 0.95842(12) -0.02222(11) 0.0235(4) Uani 1 1 d . . . . .
H2 H 0.1923 0.9594 0.0042 0.028 Uiso 1 1 calc R U . . .
C3 C 0.30211(18) 1.01979(12) -0.06253(11) 0.0239(4) Uani 1 1 d . . . . .
H3 H 0.2602 1.0723 -0.0697 0.029 Uiso 1 1 calc R U . . .
C4 C 0.34700(19) 0.81311(12) 0.00855(11) 0.0267(4) Uani 1 1 d . . . . .
H4A H 0.2995 0.8196 0.0499 0.032 Uiso 1 1 calc R U . . .
H4B H 0.4411 0.7934 0.0266 0.032 Uiso 1 1 calc R U . . .
C5 C 0.2727(2) 0.75045(12) -0.04172(13) 0.0328(5) Uani 1 1 d . . . . .
H5A H 0.3177 0.7452 -0.0834 0.049 Uiso 1 1 calc R U . . .
H5B H 0.1776 0.7680 -0.0571 0.049 Uiso 1 1 calc R U . . .
H5C H 0.2741 0.6973 -0.0174 0.049 Uiso 1 1 calc R U . . .
C6 C 0.4790(2) 1.03864(12) -0.14140(11) 0.0287(4) Uani 1 1 d . . . . .
H6A H 0.5773 1.0425 -0.1228 0.043 Uiso 1 1 calc R U . . .
H6B H 0.4397 1.0940 -0.1471 0.043 Uiso 1 1 calc R U . . .
H6C H 0.4647 1.0107 -0.1877 0.043 Uiso 1 1 calc R U . . .
C7 C 0.55410(19) 0.86365(12) -0.08864(11) 0.0255(4) Uani 1 1 d . . . . .
H7A H 0.5810 0.8218 -0.0518 0.038 Uiso 1 1 calc R U . . .
H7B H 0.6330 0.8986 -0.0924 0.038 Uiso 1 1 calc R U . . .
H7C H 0.5221 0.8367 -0.1346 0.038 Uiso 1 1 calc R U . . .
C8 C -0.02804(19) 0.81351(12) -0.17266(11) 0.0239(4) Uani 1 1 d . . . . .
C9 C 0.1257(2) 0.90109(14) -0.20035(11) 0.0313(5) Uani 1 1 d . . . . .
H9 H 0.1730 0.9508 -0.2058 0.038 Uiso 1 1 calc R U . . .
C10 C 0.1601(2) 0.82573(15) -0.22020(11) 0.0327(5) Uani 1 1 d . . . . .
H10 H 0.2366 0.8121 -0.2418 0.039 Uiso 1 1 calc R U . . .
C11 C -0.0656(2) 0.96071(12) -0.14338(11) 0.0295(5) Uani 1 1 d . . . . .
H11A H -0.0006 1.0058 -0.1272 0.035 Uiso 1 1 calc R U . . .
H11B H -0.1043 0.9415 -0.1017 0.035 Uiso 1 1 calc R U . . .
C12 C -0.1785(2) 0.99261(13) -0.19897(12) 0.0338(5) Uani 1 1 d . . . . .
H12A H -0.1412 1.0090 -0.2413 0.051 Uiso 1 1 calc R U . . .
H12B H -0.2210 1.0403 -0.1801 0.051 Uiso 1 1 calc R U . . .
H12C H -0.2473 0.9495 -0.2119 0.051 Uiso 1 1 calc R U . . .
C13 C 0.0629(2) 0.68264(13) -0.21374(13) 0.0384(6) Uani 1 1 d . . . . .
H13A H 0.0791 0.6551 -0.1672 0.058 Uiso 1 1 calc R U . . .
H13B H 0.1354 0.6676 -0.2404 0.058 Uiso 1 1 calc R U . . .
H13C H -0.0260 0.6655 -0.2406 0.058 Uiso 1 1 calc R U . . .
C14 C -0.1445(2) 0.77726(12) -0.14463(12) 0.0293(5) Uani 1 1 d . . . . .
H14A H -0.2275 0.7813 -0.1808 0.044 Uiso 1 1 calc R U . . .
H14B H -0.1581 0.8070 -0.1016 0.044 Uiso 1 1 calc R U . . .
H14C H -0.1252 0.7194 -0.1328 0.044 Uiso 1 1 calc R U . . .
C15 C 0.59100(19) 0.53915(12) -0.11989(11) 0.0241(4) Uani 1 1 d . . . . .
C16 C 0.5331(2) 0.40742(13) -0.12855(11) 0.0293(5) Uani 1 1 d . . . . .
H16 H 0.4800 0.3585 -0.1318 0.035 Uiso 1 1 calc R U . . .
C17 C 0.6687(2) 0.41252(12) -0.12663(11) 0.0265(4) Uani 1 1 d . . . . .
H17 H 0.7296 0.3679 -0.1286 0.032 Uiso 1 1 calc R U . . .
C18 C 0.3396(2) 0.50868(14) -0.12770(12) 0.0323(5) Uani 1 1 d . . . . .
H18A H 0.2816 0.4704 -0.1603 0.039 Uiso 1 1 calc R U . . .
H18B H 0.3232 0.5650 -0.1471 0.039 Uiso 1 1 calc R U . . .
C19 C 0.2995(2) 0.50454(14) -0.05490(12) 0.0347(5) Uani 1 1 d . . . . .
H19A H 0.3576 0.5419 -0.0224 0.052 Uiso 1 1 calc R U . . .
H19B H 0.3115 0.4482 -0.0366 0.052 Uiso 1 1 calc R U . . .
H19C H 0.2035 0.5208 -0.0584 0.052 Uiso 1 1 calc R U . . .
C20 C 0.84085(19) 0.52780(12) -0.12099(12) 0.0295(5) Uani 1 1 d . . . . .
H20A H 0.8399 0.5627 -0.1630 0.044 Uiso 1 1 calc R U . . .
H20B H 0.9053 0.4824 -0.1221 0.044 Uiso 1 1 calc R U . . .
H20C H 0.8693 0.5604 -0.0777 0.044 Uiso 1 1 calc R U . . .
C21 C 0.5872(2) 0.63009(12) -0.11265(13) 0.0321(5) Uani 1 1 d . . . . .
H21A H 0.6646 0.6481 -0.0768 0.048 Uiso 1 1 calc R U . . .
H21B H 0.5012 0.6464 -0.0978 0.048 Uiso 1 1 calc R U . . .
H21C H 0.5933 0.6557 -0.1586 0.048 Uiso 1 1 calc R U . . .
N1 N 0.35387(15) 0.89365(9) -0.02650(8) 0.0205(3) Uani 1 1 d . . . . .
N2 N 0.41220(15) 0.99197(9) -0.09143(9) 0.0213(3) Uani 1 1 d . . . . .
N3 N 0.00844(16) 0.89282(10) -0.17041(9) 0.0251(4) Uani 1 1 d . . . . .
N4 N 0.06323(16) 0.77204(11) -0.20316(9) 0.0269(4) Uani 1 1 d . . . . .
N5 N 0.48522(16) 0.48698(10) -0.12481(9) 0.0261(4) Uani 1 1 d . . . . .
N6 N 0.70337(16) 0.49477(10) -0.12117(9) 0.0237(4) Uani 1 1 d . . . . .
Cl1 Cl -0.03893(5) 0.63043(3) 0.21629(3) 0.02825(11) Uani 1 1 d . . . . .
Cl2 Cl -0.02926(5) 0.87064(3) 0.02968(2) 0.02169(10) Uani 1 1 d . . . . .
Cl3 Cl -0.30877(5) 0.74084(3) 0.07885(3) 0.02911(12) Uani 1 1 d . . . . .
Cl4 Cl -0.11682(5) 0.86384(3) 0.21604(3) 0.02668(11) Uani 1 1 d . . . . .
Cl5 Cl 0.21941(5) 0.78238(3) 0.17649(3) 0.02662(11) Uani 1 1 d . . . . .
Cl6 Cl 0.00596(5) 0.64855(3) 0.02861(3) 0.02644(11) Uani 1 1 d . . . . .
Y1 Y -0.04185(2) 0.75426(2) 0.12496(2) 0.01701(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.340(2) . ?
C1 N2 1.343(2) . ?
C1 C7 1.483(2) . ?
C2 C3 1.348(3) . ?
C2 N1 1.384(2) . ?
C2 H2 0.9500 . ?
C3 N2 1.381(2) . ?
C3 H3 0.9500 . ?
C4 N1 1.478(2) . ?
C4 C5 1.501(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 N2 1.462(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N3 1.339(2) . ?
C8 N4 1.339(2) . ?
C8 C14 1.476(3) . ?
C9 C10 1.344(3) . ?
C9 N3 1.388(2) . ?
C9 H9 0.9500 . ?
C10 N4 1.378(3) . ?
C10 H10 0.9500 . ?
C11 N3 1.468(2) . ?
C11 C12 1.494(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N4 1.469(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 N6 1.332(2) . ?
C15 N5 1.340(2) . ?
C15 C21 1.487(3) . ?
C16 C17 1.341(3) . ?
C16 N5 1.385(3) . ?
C16 H16 0.9500 . ?
C17 N6 1.381(2) . ?
C17 H17 0.9500 . ?
C18 N5 1.478(2) . ?
C18 C19 1.507(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 N6 1.465(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
Cl1 Y1 2.6580(5) . ?
Cl2 Y1 2.6398(5) . ?
Cl3 Y1 2.6496(5) . ?
Cl4 Y1 2.6800(5) . ?
Cl5 Y1 2.6464(5) . ?
Cl6 Y1 2.6167(5) . ?

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 C1 N2 107.34(16) . . ?
N1 C1 C7 127.11(17) . . ?
N2 C1 C7 125.55(17) . . ?
C3 C2 N1 107.08(16) . . ?
C3 C2 H2 126.5 . . ?
N1 C2 H2 126.5 . . ?
C2 C3 N2 107.12(16) . . ?
C2 C3 H3 126.4 . . ?
N2 C3 H3 126.4 . . ?
N1 C4 C5 111.76(16) . . ?
N1 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
N1 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 N4 107.49(17) . . ?
N3 C8 C14 126.69(17) . . ?
N4 C8 C14 125.79(17) . . ?
C10 C9 N3 107.35(19) . . ?
C10 C9 H9 126.3 . . ?
N3 C9 H9 126.3 . . ?
C9 C10 N4 106.93(18) . . ?
C9 C10 H10 126.5 . . ?
N4 C10 H10 126.5 . . ?
N3 C11 C12 111.86(17) . . ?
N3 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
N3 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C14 H14A 109.5 . . ?
C8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N6 C15 N5 107.60(16) . . ?
N6 C15 C21 125.17(17) . . ?
N5 C15 C21 127.21(18) . . ?
C17 C16 N5 106.95(18) . . ?
C17 C16 H16 126.5 . . ?
N5 C16 H16 126.5 . . ?
C16 C17 N6 107.31(18) . . ?
C16 C17 H17 126.3 . . ?
N6 C17 H17 126.3 . . ?
N5 C18 C19 111.49(18) . . ?
N5 C18 H18A 109.3 . . ?
C19 C18 H18A 109.3 . . ?
N5 C18 H18B 109.3 . . ?
C19 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N6 C20 H20A 109.5 . . ?
N6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C21 H21A 109.5 . . ?
C15 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C15 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 N1 C2 109.22(16) . . ?
C1 N1 C4 126.00(16) . . ?
C2 N1 C4 124.74(16) . . ?
C1 N2 C3 109.23(16) . . ?
C1 N2 C6 126.15(16) . . ?
C3 N2 C6 124.54(16) . . ?
C8 N3 C9 108.75(17) . . ?
C8 N3 C11 126.02(16) . . ?
C9 N3 C11 125.20(17) . . ?
C8 N4 C10 109.47(17) . . ?
C8 N4 C13 124.97(17) . . ?
C10 N4 C13 125.51(17) . . ?
C15 N5 C16 108.95(16) . . ?
C15 N5 C18 126.80(17) . . ?
C16 N5 C18 124.23(17) . . ?
C15 N6 C17 109.18(16) . . ?
C15 N6 C20 125.61(16) . . ?
C17 N6 C20 125.12(16) . . ?
Cl6 Y1 Cl2 87.400(17) . . ?
Cl6 Y1 Cl5 95.090(16) . . ?
Cl2 Y1 Cl5 88.321(16) . . ?
Cl6 Y1 Cl3 90.321(17) . . ?
Cl2 Y1 Cl3 89.717(16) . . ?
Cl5 Y1 Cl3 174.153(17) . . ?
Cl6 Y1 Cl1 88.673(17) . . ?
Cl2 Y1 Cl1 175.276(16) . . ?
Cl5 Y1 Cl1 89.414(17) . . ?
Cl3 Y1 Cl1 92.931(16) . . ?
Cl6 Y1 Cl4 174.141(16) . . ?
Cl2 Y1 Cl4 91.036(16) . . ?
Cl5 Y1 Cl4 90.504(16) . . ?
Cl3 Y1 Cl4 84.023(17) . . ?
Cl1 Y1 Cl4 93.129(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 0.3(2) . . . . ?
N3 C9 C10 N4 0.7(2) . . . . ?
N5 C16 C17 N6 0.5(2) . . . . ?
N2 C1 N1 C2 0.5(2) . . . . ?
C7 C1 N1 C2 -179.69(19) . . . . ?
N2 C1 N1 C4 178.30(16) . . . . ?
C7 C1 N1 C4 -1.9(3) . . . . ?
C3 C2 N1 C1 -0.5(2) . . . . ?
C3 C2 N1 C4 -178.36(17) . . . . ?
C5 C4 N1 C1 -80.2(2) . . . . ?
C5 C4 N1 C2 97.3(2) . . . . ?
N1 C1 N2 C3 -0.3(2) . . . . ?
C7 C1 N2 C3 179.91(18) . . . . ?
N1 C1 N2 C6 -177.19(17) . . . . ?
C7 C1 N2 C6 3.0(3) . . . . ?
C2 C3 N2 C1 0.0(2) . . . . ?
C2 C3 N2 C6 176.92(17) . . . . ?
N4 C8 N3 C9 0.0(2) . . . . ?
C14 C8 N3 C9 178.1(2) . . . . ?
N4 C8 N3 C11 177.86(18) . . . . ?
C14 C8 N3 C11 -4.1(3) . . . . ?
C10 C9 N3 C8 -0.4(2) . . . . ?
C10 C9 N3 C11 -178.32(18) . . . . ?
C12 C11 N3 C8 -84.5(2) . . . . ?
C12 C11 N3 C9 93.0(2) . . . . ?
N3 C8 N4 C10 0.4(2) . . . . ?
C14 C8 N4 C10 -177.7(2) . . . . ?
N3 C8 N4 C13 177.94(19) . . . . ?
C14 C8 N4 C13 -0.2(3) . . . . ?
C9 C10 N4 C8 -0.7(2) . . . . ?
C9 C10 N4 C13 -178.20(19) . . . . ?
N6 C15 N5 C16 0.6(2) . . . . ?
C21 C15 N5 C16 -178.1(2) . . . . ?
N6 C15 N5 C18 -177.98(19) . . . . ?
C21 C15 N5 C18 3.3(3) . . . . ?
C17 C16 N5 C15 -0.7(2) . . . . ?
C17 C16 N5 C18 177.97(19) . . . . ?
C19 C18 N5 C15 -95.6(2) . . . . ?
C19 C18 N5 C16 86.0(3) . . . . ?
N5 C15 N6 C17 -0.3(2) . . . . ?
C21 C15 N6 C17 178.5(2) . . . . ?
N5 C15 N6 C20 176.44(19) . . . . ?
C21 C15 N6 C20 -4.8(3) . . . . ?
C16 C17 N6 C15 -0.1(2) . . . . ?
C16 C17 N6 C20 -176.88(19) . . . . ?

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
C2 H2 Cl2 0.95 2.74 3.5422(19) 142.4 .
C3 H3 Cl4 0.95 3.08 3.693(2) 123.8 3_575
C3 H3 Cl2 0.95 2.70 3.3878(19) 129.8 3_575
C10 H10 Cl1 0.95 2.66 3.482(2) 145.1 4_675
C16 H16 Cl3 0.95 2.67 3.520(2) 149.9 3_565
C17 H17 Cl5 0.95 2.69 3.544(2) 150.2 3_665
C17 H17 Cl6 0.95 2.97 3.577(2) 122.6 3_665

_refine_diff_density_max         0.486
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.061

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_2014rmjdc106a1x
_database_code_depnum_ccdc_archive 'CCDC 1472570'
_audit_update_record             
;
2016-04-06 deposited with the CCDC.
2016-06-20 downloaded from the CCDC.
;
_audit_creation_date             2014-05-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '3(C7 H13 N2), Cl6 La'
_chemical_formula_sum            'C21 H39 Cl6 La N6'
_chemical_formula_weight         727.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
La La -0.2871 2.4523 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.0265(17)
_cell_length_b                   16.306(2)
_cell_length_c                   19.133(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.265(3)
_cell_angle_gamma                90
_cell_volume                     3087.4(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7456
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.2
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.924
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26415
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.157
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Mitegen
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.026195
_diffrn_orient_matrix_UB_12      0.006286
_diffrn_orient_matrix_UB_13      0.097397
_diffrn_orient_matrix_UB_21      0.044700
_diffrn_orient_matrix_UB_22      0.039378
_diffrn_orient_matrix_UB_23      -0.014565
_diffrn_orient_matrix_UB_31      -0.030904
_diffrn_orient_matrix_UB_32      0.040469
_diffrn_orient_matrix_UB_33      0.014545
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6315
_reflns_number_total             7055
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.036
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         7055
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0229
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0280P)²+0.8322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0552
_refine_ls_wR_factor_ref         0.0566
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C18(H18A,H18B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C17(H17), C16(H16), C2(H2), C3(H3)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C21(H21A,H21B,
 H21C), C6(H6A,H6B,H6C), C20(H20A,H20B,H20C), C5(H5A,H5B,H5C), C7(H7A,H7B,H7C),
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N4 N 0.41528(16) 0.50404(10) 0.40685(8) 0.0188(3) Uani 1 1 d . . . . .
N2 N 0.69640(17) 0.00416(10) 0.37768(9) 0.0223(4) Uani 1 1 d . . . . .
N6 N 1.43550(17) 0.23170(11) 0.19885(9) 0.0244(4) Uani 1 1 d . . . . .
N3 N 0.35636(16) 0.60178(10) 0.47175(8) 0.0183(3) Uani 1 1 d . . . . .
N1 N 0.48113(18) 0.01168(11) 0.37546(9) 0.0270(4) Uani 1 1 d . . . . .
C8 C 0.44548(19) 0.58064(12) 0.42960(10) 0.0182(4) Uani 1 1 d . . . . .
C9 C 0.26802(19) 0.53746(12) 0.47523(10) 0.0212(4) Uani 1 1 d . . . . .
H9 H 0.1946 0.5364 0.5010 0.025 Uiso 1 1 calc R . . . .
C1 C 0.5858(2) -0.04039(12) 0.37998(11) 0.0235(4) Uani 1 1 d . . . . .
N5 N 1.48603(17) 0.10889(10) 0.17055(8) 0.0229(4) Uani 1 1 d . . . . .
C10 C 0.3059(2) 0.47658(12) 0.43514(10) 0.0218(4) Uani 1 1 d . . . . .
H10 H 0.2645 0.4242 0.4278 0.026 Uiso 1 1 calc R . . . .
C17 C 1.3389(2) 0.18049(14) 0.21889(11) 0.0305(5) Uani 1 1 d . . . . .
H17 H 1.2643 0.1963 0.2408 0.037 Uiso 1 1 calc R . . . .
C16 C 1.3707(2) 0.10374(14) 0.20132(11) 0.0302(5) Uani 1 1 d . . . . .
H16 H 1.3227 0.0551 0.2087 0.036 Uiso 1 1 calc R . . . .
C2 C 0.5281(2) 0.09044(14) 0.37149(11) 0.0302(5) Uani 1 1 d . . . . .
H2 H 0.4756 0.1392 0.3686 0.036 Uiso 1 1 calc R . . . .
C3 C 0.6611(2) 0.08556(12) 0.37239(11) 0.0264(5) Uani 1 1 d . . . . .
H3 H 0.7207 0.1303 0.3698 0.032 Uiso 1 1 calc R . . . .
C15 C 1.5240(2) 0.18747(12) 0.16937(10) 0.0222(4) Uani 1 1 d . . . . .
C13 C 0.4840(2) 0.45748(13) 0.35779(11) 0.0262(5) Uani 1 1 d . . . . .
H13A H 0.4700 0.4845 0.3114 0.039 Uiso 1 1 calc GR . . . .
H13B H 0.4470 0.4018 0.3529 0.039 Uiso 1 1 calc GR . . . .
H13C H 0.5809 0.4550 0.3762 0.039 Uiso 1 1 calc GR . . . .
C12 C 0.2787(2) 0.74488(12) 0.45835(12) 0.0292(5) Uani 1 1 d . . . . .
H12A H 0.3246 0.7505 0.4171 0.044 Uiso 1 1 calc GR . . . .
H12B H 0.2799 0.7976 0.4830 0.044 Uiso 1 1 calc GR . . . .
H12C H 0.1849 0.7277 0.4428 0.044 Uiso 1 1 calc GR . . . .
C11 C 0.3503(2) 0.68158(12) 0.50777(11) 0.0237(4) Uani 1 1 d . . . . .
H11A H 0.4432 0.7006 0.5259 0.028 Uiso 1 1 calc R . . . .
H11B H 0.3022 0.6747 0.5487 0.028 Uiso 1 1 calc R . . . .
C14 C 0.5562(2) 0.63150(12) 0.41048(11) 0.0238(4) Uani 1 1 d . . . . .
H14A H 0.6349 0.5968 0.4076 0.036 Uiso 1 1 calc GR . . . .
H14B H 0.5807 0.6738 0.4467 0.036 Uiso 1 1 calc GR . . . .
H14C H 0.5263 0.6576 0.3645 0.036 Uiso 1 1 calc GR . . . .
C21 C 1.6395(2) 0.22101(13) 0.14005(12) 0.0269(5) Uani 1 1 d . . . . .
H21A H 1.6136 0.2731 0.1162 0.040 Uiso 1 1 calc GR . . . .
H21B H 1.6667 0.1821 0.1060 0.040 Uiso 1 1 calc GR . . . .
H21C H 1.7153 0.2302 0.1785 0.040 Uiso 1 1 calc GR . . . .
C18 C 1.5565(2) 0.03888(12) 0.14488(11) 0.0283(5) Uani 1 1 d . . . . .
H18A H 1.5924 0.0553 0.1017 0.034 Uiso 1 1 calc R . . . .
H18B H 1.4913 -0.0063 0.1319 0.034 Uiso 1 1 calc R . . . .
C6 C 0.8317(2) -0.02875(13) 0.37684(12) 0.0292(5) Uani 1 1 d . . . . .
H6A H 0.8625 -0.0581 0.4212 0.044 Uiso 1 1 calc GR . . . .
H6B H 0.8941 0.0164 0.3719 0.044 Uiso 1 1 calc GR . . . .
H6C H 0.8293 -0.0666 0.3369 0.044 Uiso 1 1 calc GR . . . .
C20 C 1.4381(2) 0.32157(13) 0.20564(13) 0.0359(6) Uani 1 1 d . . . . .
H20A H 1.5257 0.3388 0.2319 0.054 Uiso 1 1 calc GR . . . .
H20B H 1.3658 0.3393 0.2312 0.054 Uiso 1 1 calc GR . . . .
H20C H 1.4245 0.3465 0.1584 0.054 Uiso 1 1 calc GR . . . .
C5 C 0.3001(3) -0.00523(15) 0.44708(12) 0.0352(5) Uani 1 1 d . . . . .
H5A H 0.3568 -0.0429 0.4789 0.053 Uiso 1 1 calc GR . . . .
H5B H 0.2049 -0.0206 0.4447 0.053 Uiso 1 1 calc GR . . . .
H5C H 0.3136 0.0509 0.4651 0.053 Uiso 1 1 calc GR . . . .
C7 C 0.5829(2) -0.13090(13) 0.38635(13) 0.0332(5) Uani 1 1 d . . . . .
H7A H 0.5955 -0.1558 0.3413 0.050 Uiso 1 1 calc GR . . . .
H7B H 0.4956 -0.1480 0.3983 0.050 Uiso 1 1 calc GR . . . .
H7C H 0.6557 -0.1487 0.4237 0.050 Uiso 1 1 calc GR . . . .
C4 C 0.3381(2) -0.01006(16) 0.37445(12) 0.0357(6) Uani 1 1 d . . . . .
H4A H 0.3219 -0.0664 0.3558 0.043 Uiso 1 1 calc R . . . .
H4B H 0.2802 0.0277 0.3423 0.043 Uiso 1 1 calc R . . . .
C19 C 1.6696(2) 0.00899(14) 0.19890(12) 0.0337(5) Uani 1 1 d . . . . .
H19A H 1.7363 0.0529 0.2105 0.050 Uiso 1 1 calc GR . . . .
H19B H 1.7127 -0.0383 0.1800 0.050 Uiso 1 1 calc GR . . . .
H19C H 1.6345 -0.0074 0.2417 0.050 Uiso 1 1 calc GR . . . .
La1 La 1.03814(2) 0.25164(2) 0.37491(2) 0.01464(4) Uani 1 1 d . . . . .
Cl6 Cl 1.02228(5) 0.37590(3) 0.47226(2) 0.02063(10) Uani 1 1 d . . . . .
Cl2 Cl 0.98284(5) 0.14252(3) 0.47662(3) 0.02646(11) Uani 1 1 d . . . . .
Cl3 Cl 1.04273(6) 0.11993(3) 0.28119(3) 0.02866(12) Uani 1 1 d . . . . .
Cl5 Cl 1.12573(5) 0.36540(3) 0.28048(3) 0.02674(11) Uani 1 1 d . . . . .
Cl1 Cl 0.76734(5) 0.28253(3) 0.31965(3) 0.02685(11) Uani 1 1 d . . . . .
Cl4 Cl 1.31431(5) 0.23989(3) 0.42714(3) 0.03227(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N4 C8 1.341(2) . ?
N4 C10 1.374(2) . ?
N4 C13 1.463(2) . ?
N2 C1 1.332(3) . ?
N2 C3 1.373(3) . ?
N2 C6 1.461(2) . ?
N6 C17 1.379(3) . ?
N6 C15 1.337(3) . ?
N6 C20 1.471(3) . ?
N3 C8 1.341(2) . ?
N3 C9 1.381(2) . ?
N3 C11 1.478(2) . ?
N1 C1 1.342(3) . ?
N1 C2 1.374(3) . ?
N1 C4 1.474(3) . ?
C8 C14 1.478(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.346(3) . ?
C1 C7 1.482(3) . ?
N5 C16 1.382(3) . ?
N5 C15 1.338(3) . ?
N5 C18 1.468(3) . ?
C10 H10 0.9500 . ?
C17 H17 0.9500 . ?
C17 C16 1.347(3) . ?
C16 H16 0.9500 . ?
C2 H2 0.9500 . ?
C2 C3 1.334(3) . ?
C3 H3 0.9500 . ?
C15 C21 1.472(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 C11 1.502(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.488(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C5 C4 1.501(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
La1 Cl6 2.7742(5) . ?
La1 Cl2 2.7582(6) . ?
La1 Cl3 2.8029(6) . ?
La1 Cl5 2.8262(6) . ?
La1 Cl1 2.7963(7) . ?
La1 Cl4 2.7950(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N4 C10 109.18(16) . . ?
C8 N4 C13 125.91(17) . . ?
C10 N4 C13 124.88(17) . . ?
C1 N2 C3 108.87(17) . . ?
C1 N2 C6 125.40(17) . . ?
C3 N2 C6 125.65(18) . . ?
C17 N6 C20 125.57(18) . . ?
C15 N6 C17 109.53(18) . . ?
C15 N6 C20 124.85(18) . . ?
C8 N3 C9 109.16(16) . . ?
C8 N3 C11 126.01(16) . . ?
C9 N3 C11 124.81(16) . . ?
C1 N1 C2 108.89(18) . . ?
C1 N1 C4 126.71(19) . . ?
C2 N1 C4 124.40(19) . . ?
N4 C8 N3 107.28(16) . . ?
N4 C8 C14 125.56(18) . . ?
N3 C8 C14 127.16(17) . . ?
N3 C9 H9 126.5 . . ?
C10 C9 N3 106.91(17) . . ?
C10 C9 H9 126.5 . . ?
N2 C1 N1 107.43(18) . . ?
N2 C1 C7 124.97(19) . . ?
N1 C1 C7 127.6(2) . . ?
C16 N5 C18 125.17(18) . . ?
C15 N5 C16 108.97(17) . . ?
C15 N5 C18 125.84(18) . . ?
N4 C10 H10 126.3 . . ?
C9 C10 N4 107.47(17) . . ?
C9 C10 H10 126.3 . . ?
N6 C17 H17 126.6 . . ?
C16 C17 N6 106.72(19) . . ?
C16 C17 H17 126.6 . . ?
N5 C16 H16 126.3 . . ?
C17 C16 N5 107.33(19) . . ?
C17 C16 H16 126.3 . . ?
N1 C2 H2 126.4 . . ?
C3 C2 N1 107.11(19) . . ?
C3 C2 H2 126.4 . . ?
N2 C3 H3 126.2 . . ?
C2 C3 N2 107.69(19) . . ?
C2 C3 H3 126.2 . . ?
N6 C15 N5 107.44(18) . . ?
N6 C15 C21 125.24(19) . . ?
N5 C15 C21 127.30(18) . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
N3 C11 C12 111.27(16) . . ?
N3 C11 H11A 109.4 . . ?
N3 C11 H11B 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C8 C14 H14A 109.5 . . ?
C8 C14 H14B 109.5 . . ?
C8 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C15 C21 H21A 109.5 . . ?
C15 C21 H21B 109.5 . . ?
C15 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N5 C18 H18A 109.2 . . ?
N5 C18 H18B 109.2 . . ?
N5 C18 C19 112.11(17) . . ?
H18A C18 H18B 107.9 . . ?
C19 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N6 C20 H20A 109.5 . . ?
N6 C20 H20B 109.5 . . ?
N6 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C4 C5 111.53(18) . . ?
N1 C4 H4A 109.3 . . ?
N1 C4 H4B 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
Cl6 La1 Cl3 176.210(15) . . ?
Cl6 La1 Cl5 90.403(18) . . ?
Cl6 La1 Cl1 88.001(16) . . ?
Cl6 La1 Cl4 88.313(16) . . ?
Cl2 La1 Cl6 87.578(19) . . ?
Cl2 La1 Cl3 89.02(2) . . ?
Cl2 La1 Cl5 173.163(16) . . ?
Cl2 La1 Cl1 95.147(18) . . ?
Cl2 La1 Cl4 90.208(18) . . ?
Cl3 La1 Cl5 93.166(19) . . ?
Cl1 La1 Cl3 90.640(17) . . ?
Cl1 La1 Cl5 91.308(18) . . ?
Cl4 La1 Cl3 93.372(16) . . ?
Cl4 La1 Cl5 83.201(18) . . ?
Cl4 La1 Cl1 173.364(16) . . ?

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
C9 H9 Cl6 0.95 2.72 3.524(2) 143.0 3_666
C9 H9 Cl6 0.95 3.14 3.601(2) 112.0 1_455
C10 H10 Cl6 0.95 2.81 3.455(2) 125.8 1_455
C10 H10 Cl5 0.95 3.09 3.686(2) 122.5 1_455
C17 H17 Cl3 0.95 2.76 3.515(2) 136.6 .
C2 H2 Cl4 0.95 2.67 3.521(2) 148.9 1_455
C3 H3 Cl2 0.95 3.06 3.630(2) 119.7 .
C3 H3 Cl1 0.95 2.73 3.580(2) 149.6 .

####################################################################### 
# 
# 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_2014rmjdc1261x
_database_code_depnum_ccdc_archive 'CCDC 1472571'
_audit_update_record             
;
2016-04-06 deposited with the CCDC.
2016-06-20 downloaded from the CCDC.
;
_audit_creation_date             2014-08-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '3(C7 H13 N2), I6 La'
_chemical_formula_sum            'C21 H39 I6 La N6'
_chemical_formula_weight         1275.89
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.347(2)
_cell_length_b                   11.075(3)
_cell_length_c                   16.577(3)
_cell_angle_alpha                92.594(3)
_cell_angle_beta                 90.255(3)
_cell_angle_gamma                106.930(4)
_cell_volume                     1815.1(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5182
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.7
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.299
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.335
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1164
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16557
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_min         2.460
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
scan:
	Number of images: 256
	           Slice: -110.0000 - 18.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -70.0000
	             Phi: 225.0000
	             XTD: 45.0032
	          2theta: -20.0198
scan:
	Number of images: 256
	           Slice: -110.0000 - 18.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -70.0000
	             Phi: 0.0000
	             XTD: 45.0032
	          2theta: -20.0198
scan:
	Number of images: 132
	           Slice: -71.0000 - -5.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -30.0000
	             Phi: 45.0000
	             XTD: 45.0032
	          2theta: -20.0198
scan:
	Number of images: 88
	           Slice: -90.0000 - -46.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -30.0000
	             Phi: 135.0000
	             XTD: 45.0032
	          2theta: -20.0198
scan:
	Number of images: 54
	           Slice: -110.0000 - -83.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -30.0000
	             Phi: 270.0000
	             XTD: 45.0032
	          2theta: -20.0198
;
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.037343
_diffrn_orient_matrix_UB_12      -0.081532
_diffrn_orient_matrix_UB_13      -0.046556
_diffrn_orient_matrix_UB_21      0.088622
_diffrn_orient_matrix_UB_22      0.020874
_diffrn_orient_matrix_UB_23      -0.025297
_diffrn_orient_matrix_UB_31      0.022826
_diffrn_orient_matrix_UB_32      -0.020608
_diffrn_orient_matrix_UB_33      0.051982
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           55.0
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7810
_reflns_number_total             8311
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         8311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0209
_refine_ls_R_factor_gt           0.0189
_refine_ls_restrained_S_all      0.984
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0110P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0412
_refine_ls_wR_factor_ref         0.0421
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C11(H11A,H11B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C10(H10), C2(H2), C16(H16), C9(H9), C3(H3)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C),
 C12(H12A,H12B,H12C), C21(H21A,H21B,H21C), C20(H20A,H20B,H20C), C19(H19A,H19B,
 H19C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
La1 La 0.5000 0.0000 0.5000 0.01238(5) Uani 1 2 d S T P . .
La2 La 0.0000 -0.5000 0.0000 0.01347(5) Uani 1 2 d S T P . .
I2 I 0.45640(2) -0.02478(2) 0.31082(2) 0.01673(4) Uani 1 1 d . . . . .
I1 I 0.81621(2) 0.09243(2) 0.46987(2) 0.01861(4) Uani 1 1 d . . . . .
I4 I 0.25445(2) -0.26734(2) 0.05022(2) 0.01763(4) Uani 1 1 d . . . . .
I3 I 0.49400(2) -0.28991(2) 0.48846(2) 0.01738(4) Uani 1 1 d . . . . .
I6 I 0.14010(2) -0.68799(2) 0.07939(2) 0.02214(5) Uani 1 1 d . . . . .
I5 I -0.12625(2) -0.47251(2) 0.17039(2) 0.02122(5) Uani 1 1 d . . . . .
N2 N 0.4568(2) -0.4936(2) 0.24233(14) 0.0175(5) Uani 1 1 d . . . . .
N1 N 0.5142(2) -0.6600(2) 0.20576(14) 0.0165(5) Uani 1 1 d . . . . .
N3 N -0.1092(2) -0.3399(2) 0.39501(15) 0.0174(5) Uani 1 1 d . . . . .
N4 N -0.0148(2) -0.4894(2) 0.38421(15) 0.0197(5) Uani 1 1 d . . . . .
N6 N 0.0550(2) -0.9551(2) 0.23005(15) 0.0203(5) Uani 1 1 d . . . . .
C1 C 0.4928(3) -0.5548(3) 0.17924(17) 0.0165(6) Uani 1 1 d . . . . .
N5 N -0.0888(2) -1.0170(2) 0.13096(15) 0.0189(5) Uani 1 1 d . . . . .
C15 C -0.0580(3) -0.9404(3) 0.19736(18) 0.0181(6) Uani 1 1 d . . . . .
C4 C 0.5564(3) -0.7557(3) 0.15669(17) 0.0193(6) Uani 1 1 d . . . . .
H4A H 0.6016 -0.8011 0.1923 0.023 Uiso 1 1 calc R . . . .
H4B H 0.6229 -0.7128 0.1167 0.023 Uiso 1 1 calc R . . . .
C17 C 0.0955(3) -1.0434(3) 0.18251(18) 0.0215(6) Uani 1 1 d . . . . .
H17 H 0.1727 -1.0712 0.1917 0.026 Uiso 1 1 calc R . . . .
C10 C -0.1408(3) -0.5409(3) 0.41696(19) 0.0240(6) Uani 1 1 d . . . . .
H10 H -0.1785 -0.6257 0.4317 0.029 Uiso 1 1 calc R . . . .
C6 C 0.4192(3) -0.3761(3) 0.23890(19) 0.0240(6) Uani 1 1 d . . . . .
H6A H 0.4861 -0.3155 0.2077 0.036 Uiso 1 1 calc GR . . . .
H6B H 0.4164 -0.3404 0.2938 0.036 Uiso 1 1 calc GR . . . .
H6C H 0.3300 -0.3939 0.2129 0.036 Uiso 1 1 calc GR . . . .
C2 C 0.4901(3) -0.6651(3) 0.28773(17) 0.0184(6) Uani 1 1 d . . . . .
H2 H 0.4971 -0.7300 0.3215 0.022 Uiso 1 1 calc R . . . .
C8 C 0.0017(3) -0.3678(3) 0.37057(17) 0.0182(6) Uani 1 1 d . . . . .
C7 C 0.5104(3) -0.5115(3) 0.09574(17) 0.0215(6) Uani 1 1 d . . . . .
H7A H 0.4424 -0.4689 0.0834 0.032 Uiso 1 1 calc GR . . . .
H7B H 0.4997 -0.5844 0.0578 0.032 Uiso 1 1 calc GR . . . .
H7C H 0.6010 -0.4525 0.0907 0.032 Uiso 1 1 calc GR . . . .
C11 C -0.1382(3) -0.2175(3) 0.39068(18) 0.0199(6) Uani 1 1 d . . . . .
H11A H -0.0521 -0.1484 0.3942 0.024 Uiso 1 1 calc R . . . .
H11B H -0.1934 -0.2059 0.4374 0.024 Uiso 1 1 calc R . . . .
C16 C 0.0058(3) -1.0824(3) 0.12113(19) 0.0220(6) Uani 1 1 d . . . . .
H16 H 0.0070 -1.1432 0.0791 0.026 Uiso 1 1 calc R . . . .
C9 C -0.1996(3) -0.4468(3) 0.42379(18) 0.0216(6) Uani 1 1 d . . . . .
H9 H -0.2867 -0.4530 0.4445 0.026 Uiso 1 1 calc R . . . .
C3 C 0.4550(3) -0.5612(3) 0.31065(17) 0.0202(6) Uani 1 1 d . . . . .
H3 H 0.4332 -0.5385 0.3637 0.024 Uiso 1 1 calc R . . . .
C13 C 0.0816(3) -0.5590(3) 0.3624(2) 0.0303(7) Uani 1 1 d . . . . .
H13A H 0.0525 -0.6428 0.3848 0.045 Uiso 1 1 calc GR . . . .
H13B H 0.1713 -0.5125 0.3843 0.045 Uiso 1 1 calc GR . . . .
H13C H 0.0855 -0.5681 0.3034 0.045 Uiso 1 1 calc GR . . . .
C14 C 0.1226(3) -0.2832(3) 0.33298(19) 0.0226(6) Uani 1 1 d . . . . .
H14A H 0.1259 -0.3105 0.2762 0.034 Uiso 1 1 calc GR . . . .
H14B H 0.2043 -0.2872 0.3615 0.034 Uiso 1 1 calc GR . . . .
H14C H 0.1172 -0.1963 0.3365 0.034 Uiso 1 1 calc GR . . . .
C18 C -0.2082(3) -1.0335(3) 0.07766(19) 0.0263(7) Uani 1 1 d . . . . .
H18A H -0.1888 -1.0614 0.0226 0.032 Uiso 1 1 calc R . . . .
H18B H -0.2281 -0.9517 0.0742 0.032 Uiso 1 1 calc R . . . .
C12 C -0.2126(3) -0.2091(3) 0.31344(19) 0.0245(6) Uani 1 1 d . . . . .
H12A H -0.1545 -0.2118 0.2673 0.037 Uiso 1 1 calc GR . . . .
H12B H -0.2365 -0.1297 0.3149 0.037 Uiso 1 1 calc GR . . . .
H12C H -0.2950 -0.2805 0.3080 0.037 Uiso 1 1 calc GR . . . .
C21 C -0.1350(3) -0.8548(3) 0.2285(2) 0.0252(7) Uani 1 1 d . . . . .
H21A H -0.0943 -0.8135 0.2799 0.038 Uiso 1 1 calc GR . . . .
H21B H -0.2289 -0.9039 0.2370 0.038 Uiso 1 1 calc GR . . . .
H21C H -0.1325 -0.7906 0.1893 0.038 Uiso 1 1 calc GR . . . .
C20 C 0.1279(3) -0.8847(3) 0.3015(2) 0.0301(7) Uani 1 1 d . . . . .
H20A H 0.1733 -0.7974 0.2881 0.045 Uiso 1 1 calc GR . . . .
H20B H 0.1952 -0.9248 0.3194 0.045 Uiso 1 1 calc GR . . . .
H20C H 0.0639 -0.8847 0.3449 0.045 Uiso 1 1 calc GR . . . .
C19 C -0.3293(3) -1.1300(4) 0.1098(2) 0.0337(8) Uani 1 1 d . . . . .
H19A H -0.4076 -1.1395 0.0740 0.050 Uiso 1 1 calc GR . . . .
H19B H -0.3488 -1.1020 0.1641 0.050 Uiso 1 1 calc GR . . . .
H19C H -0.3101 -1.2114 0.1122 0.050 Uiso 1 1 calc GR . . . .
C5 C 0.4390(3) -0.8507(3) 0.11257(19) 0.0236(6) Uani 1 1 d . . . . .
H5A H 0.3937 -0.8063 0.0773 0.035 Uiso 1 1 calc GR . . . .
H5B H 0.3748 -0.8963 0.1519 0.035 Uiso 1 1 calc GR . . . .
H5C H 0.4725 -0.9108 0.0799 0.035 Uiso 1 1 calc GR . . . .


_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 I2 3.1545(6) 2_656 ?
La1 I2 3.1545(6) . ?
La1 I1 3.1800(7) . ?
La1 I1 3.1800(7) 2_656 ?
La1 I3 3.1903(7) 2_656 ?
La1 I3 3.1903(7) . ?
La2 I4 3.1779(5) 2_545 ?
La2 I4 3.1780(5) . ?
La2 I6 3.1869(5) 2_545 ?
La2 I6 3.1870(5) . ?
La2 I5 3.1565(5) 2_545 ?
La2 I5 3.1566(5) . ?
N2 C1 1.333(4) . ?
N2 C6 1.466(4) . ?
N2 C3 1.383(4) . ?
N1 C1 1.340(4) . ?
N1 C4 1.474(4) . ?
N1 C2 1.383(3) . ?
N3 C8 1.333(4) . ?
N3 C11 1.476(4) . ?
N3 C9 1.384(4) . ?
N4 C10 1.386(4) . ?
N4 C8 1.337(4) . ?
N4 C13 1.465(4) . ?
N6 C15 1.341(3) . ?
N6 C17 1.387(4) . ?
N6 C20 1.465(4) . ?
C1 C7 1.480(4) . ?
N5 C15 1.337(4) . ?
N5 C16 1.383(4) . ?
N5 C18 1.478(4) . ?
C15 C21 1.483(4) . ?
C4 C5 1.515(4) . ?
C17 C16 1.342(4) . ?
C10 C9 1.351(4) . ?
C2 C3 1.343(4) . ?
C8 C14 1.485(4) . ?
C11 C12 1.511(4) . ?
C18 C19 1.508(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
I2 La1 I2 180.0 2_656 . ?
I2 La1 I1 87.778(8) . . ?
I2 La1 I1 92.221(7) 2_656 . ?
I2 La1 I1 92.221(7) . 2_656 ?
I2 La1 I1 87.779(7) 2_656 2_656 ?
I2 La1 I3 86.451(6) . . ?
I2 La1 I3 93.549(6) 2_656 . ?
I2 La1 I3 93.550(6) . 2_656 ?
I2 La1 I3 86.450(6) 2_656 2_656 ?
I1 La1 I1 180.0 2_656 . ?
I1 La1 I3 92.133(8) . . ?
I1 La1 I3 87.867(8) 2_656 . ?
I1 La1 I3 87.868(8) . 2_656 ?
I1 La1 I3 92.132(8) 2_656 2_656 ?
I3 La1 I3 180.0 . 2_656 ?
I4 La2 I4 180.0 2_545 . ?
I4 La2 I6 89.775(18) . 2_545 ?
I4 La2 I6 89.774(17) 2_545 . ?
I4 La2 I6 90.225(18) . . ?
I4 La2 I6 90.225(18) 2_545 2_545 ?
I6 La2 I6 180.0 2_545 . ?
I5 La2 I4 89.575(11) . . ?
I5 La2 I4 90.425(11) 2_545 . ?
I5 La2 I4 89.576(11) 2_545 2_545 ?
I5 La2 I4 90.424(11) . 2_545 ?
I5 La2 I6 87.114(12) . . ?
I5 La2 I6 92.885(12) 2_545 . ?
I5 La2 I6 87.114(12) 2_545 2_545 ?
I5 La2 I6 92.886(12) . 2_545 ?
I5 La2 I5 180.0 2_545 . ?
C1 N2 C6 125.2(2) . . ?
C1 N2 C3 109.3(2) . . ?
C3 N2 C6 125.4(2) . . ?
C1 N1 C4 126.3(2) . . ?
C1 N1 C2 108.8(2) . . ?
C2 N1 C4 124.8(2) . . ?
C8 N3 C11 127.2(2) . . ?
C8 N3 C9 109.3(2) . . ?
C9 N3 C11 123.5(2) . . ?
C10 N4 C13 125.6(3) . . ?
C8 N4 C10 109.4(2) . . ?
C8 N4 C13 124.9(3) . . ?
C15 N6 C17 108.6(2) . . ?
C15 N6 C20 125.8(2) . . ?
C17 N6 C20 125.5(2) . . ?
N2 C1 N1 107.6(2) . . ?
N2 C1 C7 126.0(3) . . ?
N1 C1 C7 126.4(3) . . ?
C15 N5 C16 109.5(2) . . ?
C15 N5 C18 125.6(2) . . ?
C16 N5 C18 124.9(3) . . ?
N6 C15 C21 126.6(3) . . ?
N5 C15 N6 107.5(2) . . ?
N5 C15 C21 125.9(3) . . ?
N1 C4 C5 112.7(2) . . ?
C16 C17 N6 107.6(2) . . ?
C9 C10 N4 106.6(3) . . ?
C3 C2 N1 107.3(3) . . ?
N3 C8 N4 107.6(2) . . ?
N3 C8 C14 127.7(3) . . ?
N4 C8 C14 124.6(3) . . ?
N3 C11 C12 112.0(2) . . ?
C17 C16 N5 106.7(3) . . ?
C10 C9 N3 107.1(3) . . ?
C2 C3 N2 106.9(3) . . ?
N5 C18 C19 110.5(2) . . ?

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
C17 H17 I4 0.95 3.40 3.948(3) 118.8 1_545
C10 H10 I3 0.95 3.41 3.956(3) 118.5 2_546
C2 H2 I2 0.95 3.16 3.933(3) 139.2 1_545
C2 H2 I3 0.95 3.15 3.775(3) 125.2 2_646
C16 H16 I4 0.95 3.27 3.883(3) 124.3 1_545
C9 H9 I3 0.95 3.27 3.892(3) 124.8 2_546
C3 H3 I3 0.95 3.38 3.883(3) 115.3 2_646

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 0.5(3) . . . . ?
N4 C10 C9 N3 0.2(3) . . . . ?
N6 C17 C16 N5 0.5(3) . . . . ?
C1 N2 C3 C2 -0.3(3) . . . . ?
C1 N1 C4 C5 -82.9(3) . . . . ?
C1 N1 C2 C3 -0.5(3) . . . . ?
C15 N6 C17 C16 -0.3(3) . . . . ?
C15 N5 C16 C17 -0.5(3) . . . . ?
C15 N5 C18 C19 -84.9(4) . . . . ?
C4 N1 C1 N2 -179.6(2) . . . . ?
C4 N1 C1 C7 -1.6(4) . . . . ?
C4 N1 C2 C3 179.5(2) . . . . ?
C17 N6 C15 N5 0.0(3) . . . . ?
C17 N6 C15 C21 -179.8(3) . . . . ?
C10 N4 C8 N3 1.1(3) . . . . ?
C10 N4 C8 C14 -177.7(3) . . . . ?
C6 N2 C1 N1 -177.5(2) . . . . ?
C6 N2 C1 C7 4.5(4) . . . . ?
C6 N2 C3 C2 177.2(3) . . . . ?
C2 N1 C1 N2 0.4(3) . . . . ?
C2 N1 C1 C7 178.4(3) . . . . ?
C2 N1 C4 C5 97.1(3) . . . . ?
C8 N3 C11 C12 91.8(3) . . . . ?
C8 N3 C9 C10 0.5(3) . . . . ?
C8 N4 C10 C9 -0.8(3) . . . . ?
C11 N3 C8 N4 -178.9(3) . . . . ?
C11 N3 C8 C14 -0.2(5) . . . . ?
C11 N3 C9 C10 178.5(3) . . . . ?
C16 N5 C15 N6 0.3(3) . . . . ?
C16 N5 C15 C21 -179.9(3) . . . . ?
C16 N5 C18 C19 92.6(3) . . . . ?
C9 N3 C8 N4 -0.9(3) . . . . ?
C9 N3 C8 C14 177.7(3) . . . . ?
C9 N3 C11 C12 -85.8(3) . . . . ?
C3 N2 C1 N1 -0.1(3) . . . . ?
C3 N2 C1 C7 -178.1(3) . . . . ?
C13 N4 C10 C9 -176.7(3) . . . . ?
C13 N4 C8 N3 177.0(3) . . . . ?
C13 N4 C8 C14 -1.7(5) . . . . ?
C18 N5 C15 N6 178.1(3) . . . . ?
C18 N5 C15 C21 -2.1(5) . . . . ?
C18 N5 C16 C17 -178.4(3) . . . . ?
C20 N6 C15 N5 177.0(3) . . . . ?
C20 N6 C15 C21 -2.8(5) . . . . ?
C20 N6 C17 C16 -177.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
