# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_kk1401
_database_code_depnum_ccdc_archive 'CCDC 1478230'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H56 Cl4 La2 O12'
_chemical_formula_sum            'C24 H56 Cl4 La2 O12'
_chemical_formula_weight         956.31

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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   11.3100(2)
_cell_length_b                   10.2958(2)
_cell_length_c                   17.6004(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.490(1)
_cell_angle_gamma                90.00
_cell_volume                     2040.09(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    11632
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      33.73

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             956
_exptl_absorpt_coefficient_mu    2.374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.629
_exptl_absorpt_correction_T_max  0.754
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

_exptl_special_details           
; 
 The -OH hydrogen atom on atom O3 was the 4th highest peak in the final difference 
 map and it's position is reasonable vis-a-vis H-bonding to Cl.  Although its
 position was refined satisfactorily, it should not be regarded as 'located 
 accurately'. 
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_reflns_number            18515
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0617
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.62
_diffrn_reflns_theta_max         33.75
_reflns_number_total             8079
_reflns_number_gt                5461
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0142P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8079
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0564
_refine_ls_wR_factor_gt          0.0548
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
La1 La 0.875358(10) 0.072215(11) 0.425019(6) 0.02366(4) Uani 1 1 d . . .
Cl1 Cl 0.67198(5) -0.07624(6) 0.37906(4) 0.04186(14) Uani 1 1 d . . .
Cl2 Cl 1.02349(5) -0.00434(6) 0.30979(3) 0.03427(12) Uani 1 1 d . . .
O1 O 0.67685(16) 0.29087(17) 0.59507(9) 0.0487(4) Uani 1 1 d . . .
C1 C 0.6992(3) 0.3951(3) 0.64739(17) 0.0685(9) Uani 1 1 d . . .
H1A H 0.7147 0.4746 0.6193 0.103 Uiso 1 1 calc R . .
H1B H 0.7686 0.3745 0.6831 0.103 Uiso 1 1 calc R . .
H1C H 0.6298 0.4082 0.6759 0.103 Uiso 1 1 calc R . .
C2 C 0.6551(2) 0.1704(2) 0.63181(13) 0.0451(6) Uani 1 1 d . . .
H2A H 0.5743 0.1709 0.6491 0.054 Uiso 1 1 calc R . .
H2B H 0.7131 0.1589 0.6771 0.054 Uiso 1 1 calc R . .
O3 O 0.78366(14) 0.05661(16) 0.55325(9) 0.0367(4) Uani 1 1 d D . .
H3A H 0.835(2) 0.043(2) 0.5923(13) 0.044 Uiso 1 1 d . . .
C3 C 0.6663(2) 0.0606(2) 0.57691(14) 0.0387(6) Uani 1 1 d . . .
H3 H 0.6099 0.0777 0.5307 0.046 Uiso 1 1 calc RD . .
C4 C 0.6319(2) -0.0681(2) 0.61078(19) 0.0585(8) Uani 1 1 d . . .
H4A H 0.6425 -0.1381 0.5743 0.088 Uiso 1 1 calc R . .
H4B H 0.5486 -0.0648 0.6217 0.088 Uiso 1 1 calc R . .
H4C H 0.6826 -0.0844 0.6582 0.088 Uiso 1 1 calc R . .
O5 O 0.76350(14) 0.20134(15) 0.30791(8) 0.0369(4) Uani 1 1 d . . .
C5 C 0.7409(3) 0.1389(3) 0.23491(13) 0.0571(8) Uani 1 1 d . . .
H5A H 0.7384 0.2043 0.1944 0.086 Uiso 1 1 calc R . .
H5B H 0.6645 0.0934 0.2325 0.086 Uiso 1 1 calc R . .
H5C H 0.8043 0.0763 0.2281 0.086 Uiso 1 1 calc R . .
C6 C 0.6653(2) 0.2806(3) 0.32313(14) 0.0520(7) Uani 1 1 d . . .
H6A H 0.5947 0.2255 0.3281 0.062 Uiso 1 1 calc R . .
H6B H 0.6461 0.3417 0.2803 0.062 Uiso 1 1 calc R . .
O7 O 0.73939(14) 0.26314(14) 0.45302(8) 0.0388(4) Uani 1 1 d . . .
C7 C 0.6950(2) 0.3542(3) 0.39466(14) 0.0506(7) Uani 1 1 d . . .
H7 H 0.7615 0.4148 0.3858 0.061 Uiso 1 1 calc R . .
C8 C 0.5952(3) 0.4344(3) 0.42005(18) 0.0790(11) Uani 1 1 d . . .
H8A H 0.6255 0.4904 0.4626 0.118 Uiso 1 1 calc R . .
H8B H 0.5336 0.3770 0.4366 0.118 Uiso 1 1 calc R . .
H8C H 0.5615 0.4883 0.3775 0.118 Uiso 1 1 calc R . .
O9 O 0.99792(13) 0.29163(14) 0.39648(8) 0.0325(3) Uani 1 1 d . . .
C9 C 1.0159(2) 0.3380(2) 0.32139(12) 0.0435(6) Uani 1 1 d . . .
H9A H 1.0407 0.4292 0.3244 0.065 Uiso 1 1 calc R . .
H9B H 0.9415 0.3305 0.2882 0.065 Uiso 1 1 calc R . .
H9C H 1.0776 0.2860 0.3004 0.065 Uiso 1 1 calc R . .
C10 C 1.1068(2) 0.3011(2) 0.44581(12) 0.0358(5) Uani 1 1 d . . .
H10A H 1.1330 0.3928 0.4497 0.043 Uiso 1 1 calc R . .
H10B H 1.1698 0.2498 0.4244 0.043 Uiso 1 1 calc R . .
O11 O 1.03817(12) 0.12235(13) 0.51670(7) 0.0260(3) Uani 1 1 d . . .
C11 C 1.0862(2) 0.24984(19) 0.52418(12) 0.0309(5) Uani 1 1 d . . .
H11 H 1.1651 0.2438 0.5549 0.037 Uiso 1 1 calc R . .
C12 C 1.0077(2) 0.3386(2) 0.56641(12) 0.0396(6) Uani 1 1 d . . .
H12A H 0.9971 0.3013 0.6166 0.059 Uiso 1 1 calc R . .
H12B H 0.9301 0.3475 0.5369 0.059 Uiso 1 1 calc R . .
H12C H 1.0451 0.4242 0.5730 0.059 Uiso 1 1 calc R . .


_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 O11 2.3859(13) . ?
La1 O11 2.4144(13) 3_756 ?
La1 O7 2.5723(14) . ?
La1 O3 2.5773(15) . ?
La1 O5 2.6678(14) . ?
La1 O9 2.7222(14) . ?
La1 Cl1 2.8152(6) . ?
La1 Cl2 2.8620(5) . ?
La1 La1 3.9627(2) 3_756 ?
O1 C1 1.421(3) . ?
O1 C2 1.431(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.500(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
O3 C3 1.429(3) . ?
O3 H3A 0.87(2) . ?
C3 C4 1.519(3) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
O5 C6 1.424(3) . ?
O5 C5 1.438(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.481(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
O7 C7 1.445(3) . ?
C7 C8 1.501(3) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O9 C9 1.438(2) . ?
O9 C10 1.440(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.516(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
O11 C11 1.422(2) . ?
O11 La1 2.4144(13) 3_756 ?
C11 C12 1.517(3) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
O11 La1 O11 68.72(5) . 3_756 ?
O11 La1 O7 98.16(5) . . ?
O11 La1 O7 141.07(5) 3_756 . ?
O11 La1 O3 76.73(5) . . ?
O11 La1 O3 75.93(5) 3_756 . ?
O7 La1 O3 65.28(5) . . ?
O11 La1 O5 133.87(5) . . ?
O11 La1 O5 152.20(5) 3_756 . ?
O7 La1 O5 61.26(5) . . ?
O3 La1 O5 120.45(5) . . ?
O11 La1 O9 64.63(4) . . ?
O11 La1 O9 125.04(4) 3_756 . ?
O7 La1 O9 74.07(5) . . ?
O3 La1 O9 117.90(5) . . ?
O5 La1 O9 69.89(5) . . ?
O11 La1 Cl1 150.26(3) . . ?
O11 La1 Cl1 87.61(3) 3_756 . ?
O7 La1 Cl1 89.02(4) . . ?
O3 La1 Cl1 80.30(4) . . ?
O5 La1 Cl1 74.61(4) . . ?
O9 La1 Cl1 144.49(3) . . ?
O11 La1 Cl2 94.16(3) . . ?
O11 La1 Cl2 80.32(3) 3_756 . ?
O7 La1 Cl2 138.37(3) . . ?
O3 La1 Cl2 156.23(4) . . ?
O5 La1 Cl2 81.74(4) . . ?
O9 La1 Cl2 75.81(3) . . ?
Cl1 La1 Cl2 99.467(18) . . ?
O11 La1 La1 34.59(3) . 3_756 ?
O11 La1 La1 34.13(3) 3_756 3_756 ?
O7 La1 La1 124.02(3) . 3_756 ?
O3 La1 La1 73.36(3) . 3_756 ?
O5 La1 La1 162.98(4) . 3_756 ?
O9 La1 La1 95.27(3) . 3_756 ?
Cl1 La1 La1 119.824(13) . 3_756 ?
Cl2 La1 La1 86.629(11) . 3_756 ?
C1 O1 C2 112.9(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 109.46(19) . . ?
O1 C2 H2A 109.8 . . ?
C3 C2 H2A 109.8 . . ?
O1 C2 H2B 109.8 . . ?
C3 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
C3 O3 La1 135.73(14) . . ?
C3 O3 H3A 109.9(17) . . ?
La1 O3 H3A 114.3(17) . . ?
O3 C3 C2 110.3(2) . . ?
O3 C3 C4 111.64(19) . . ?
C2 C3 C4 111.3(2) . . ?
O3 C3 H3 107.8 . . ?
C2 C3 H3 107.8 . . ?
C4 C3 H3 107.8 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 O5 C5 110.42(18) . . ?
C6 O5 La1 117.45(13) . . ?
C5 O5 La1 119.88(14) . . ?
O5 C5 H5A 109.5 . . ?
O5 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O5 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O5 C6 C7 109.6(2) . . ?
O5 C6 H6A 109.8 . . ?
C7 C6 H6A 109.8 . . ?
O5 C6 H6B 109.8 . . ?
C7 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
C7 O7 La1 122.21(13) . . ?
O7 C7 C6 107.9(2) . . ?
O7 C7 C8 111.4(2) . . ?
C6 C7 C8 114.7(2) . . ?
O7 C7 H7 107.5 . . ?
C6 C7 H7 107.5 . . ?
C8 C7 H7 107.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C9 O9 C10 110.12(16) . . ?
C9 O9 La1 124.37(12) . . ?
C10 O9 La1 111.46(11) . . ?
O9 C9 H9A 109.5 . . ?
O9 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O9 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O9 C10 C11 109.15(17) . . ?
O9 C10 H10A 109.9 . . ?
C11 C10 H10A 109.9 . . ?
O9 C10 H10B 109.9 . . ?
C11 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C11 O11 La1 121.70(11) . . ?
C11 O11 La1 126.24(11) . 3_756 ?
La1 O11 La1 111.28(5) . 3_756 ?
O11 C11 C10 109.14(16) . . ?
O11 C11 C12 111.42(18) . . ?
C10 C11 C12 112.61(18) . . ?
O11 C11 H11 107.8 . . ?
C10 C11 H11 107.8 . . ?
C12 C11 H11 107.8 . . ?
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 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        33.75
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         1.023
_refine_diff_density_min         -0.811
_refine_diff_density_rms         0.087
