# Electronic Supplementary Material (ESI) for ChemComm.
# 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_DW_B2_0064
_database_code_depnum_ccdc_archive 'CCDC 1454030'
_audit_update_record             
;
2016-02-17 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;
#===============================================================================
# H atom on Sn is **DISORDERED**
# There is one H atom on Sn, either above or below the horizontal mirror plane
# The H atom also lies in the vertical mirror plane
#===============================================================================
_audit_creation_method           SHELXL-2014/7

#-------------------------------------------------------------------------------
# Inserted by local software: cifUpdate ver. 3.0  (Andrew D. Bond, July 2015)
#-------------------------------------------------------------------------------
_cambridge_user_name             'Raul Garcia-Rodriguez'
_cambridge_user_crsid            rg589
_cambridge_supervisor_name       'Dominic Wright'
_cambridge_supervisor_crsid      dsw1000
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             MF051
_cambridge_data_id               DW_B2_0064

_database_code_CSD               ?
#-------------------------------------------------------------------------------

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H57 B2 Li N2 P2 Sn'
_chemical_formula_sum            'C20 H57 B2 Li N2 P2 Sn'
_chemical_formula_weight         534.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn 0.0259 5.4591 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Li Li 0.0008 0.0003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           63
_space_group_name_H-M_alt        'C m c m'
_space_group_name_Hall           '-C 2c 2'

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

_cell_length_a                   18.9850(8)
_cell_length_b                   10.8911(5)
_cell_length_c                   14.8749(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3075.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9957
_cell_measurement_theta_min      4.65
_cell_measurement_theta_max      70.21

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    7.625
_shelx_estimated_absorpt_T_min   0.297
_shelx_estimated_absorpt_T_max   0.461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5532
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18658
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.658
_diffrn_reflns_theta_max         70.208
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1576
_reflns_number_gt                1477
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_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)+(0.0212P)²+4.6457P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1576
_refine_ls_number_parameters     112
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0561
_refine_ls_wR_factor_gt          0.0546
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.229
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.047

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
Sn1 Sn 0.5000 0.78893(2) 0.7500 0.04130(11) Uani 1 4 d S T P . .
H100 H 0.5000 0.7516 0.6967 0.062 Uiso 0.5 2 d R U P . .
P1 P 0.38944(3) 0.64100(6) 0.7500 0.02769(15) Uani 1 2 d S T P A .
N1 N 0.5000 0.2152(3) 0.6343(3) 0.0616(8) Uani 1 2 d S T P . .
H1 H 0.5000 0.273(5) 0.598(4) 0.096(19) Uiso 1 2 d S . P . .
B1 B 0.3982(2) 0.4622(3) 0.7500 0.0581(12) Uani 1 2 d S T P . .
H11 H 0.4302(13) 0.438(2) 0.6899(15) 0.054(7) Uiso 1 1 d . . . . .
H12 H 0.349(3) 0.421(4) 0.7500 0.095(15) Uiso 1 2 d S . P . .
Li1 Li 0.5000 0.3252(6) 0.7500 0.0371(15) Uani 1 4 d S T P . .
C1 C 0.4364(2) 0.1440(3) 0.6207(3) 0.1000(13) Uani 1 1 d . . . . .
H1B H 0.4373 0.1071 0.5606 0.150 Uiso 1 1 calc R U . . .
H1C H 0.3953 0.1978 0.6261 0.150 Uiso 1 1 calc R U . . .
H1D H 0.4338 0.0791 0.6662 0.150 Uiso 1 1 calc R U . . .
C2 C 0.33910(13) 0.6851(2) 0.64585(16) 0.0531(6) Uani 1 1 d D . . . .
C3A C 0.2851(3) 0.5875(6) 0.6210(4) 0.0659(19) Uani 0.527(7) 1 d D . P A 1
H31A H 0.3052 0.5059 0.6315 0.099 Uiso 0.527(7) 1 calc R U P A 1
H32A H 0.2429 0.5980 0.6581 0.099 Uiso 0.527(7) 1 calc R U P A 1
H33A H 0.2725 0.5959 0.5574 0.099 Uiso 0.527(7) 1 calc R U P A 1
C4A C 0.4022(3) 0.6594(6) 0.5717(3) 0.0626(16) Uani 0.527(7) 1 d D . P A 1
H41A H 0.4187 0.5745 0.5775 0.094 Uiso 0.527(7) 1 calc R U P A 1
H42A H 0.3838 0.6726 0.5109 0.094 Uiso 0.527(7) 1 calc R U P A 1
H43A H 0.4414 0.7158 0.5827 0.094 Uiso 0.527(7) 1 calc R U P A 1
C5A C 0.3166(4) 0.8137(6) 0.6337(8) 0.059(3) Uani 0.527(7) 1 d D . P A 1
H51A H 0.3550 0.8688 0.6515 0.089 Uiso 0.527(7) 1 calc R U P A 1
H52A H 0.3048 0.8279 0.5704 0.089 Uiso 0.527(7) 1 calc R U P A 1
H53A H 0.2752 0.8299 0.6711 0.089 Uiso 0.527(7) 1 calc R U P A 1
C3B C 0.2558(2) 0.6532(5) 0.6614(4) 0.0556(18) Uani 0.473(7) 1 d D . P A 2
H3B1 H 0.2394 0.6923 0.7169 0.083 Uiso 0.473(7) 1 calc R U P A 2
H3B2 H 0.2283 0.6841 0.6104 0.083 Uiso 0.473(7) 1 calc R U P A 2
H3B3 H 0.2497 0.5640 0.6661 0.083 Uiso 0.473(7) 1 calc R U P A 2
C4B C 0.3623(4) 0.6276(6) 0.5648(4) 0.064(2) Uani 0.473(7) 1 d D . P A 2
H4B1 H 0.3628 0.5383 0.5729 0.096 Uiso 0.473(7) 1 calc R U P A 2
H4B2 H 0.3302 0.6489 0.5157 0.096 Uiso 0.473(7) 1 calc R U P A 2
H4B3 H 0.4099 0.6561 0.5501 0.096 Uiso 0.473(7) 1 calc R U P A 2
C5B C 0.3368(5) 0.8283(5) 0.6386(9) 0.052(2) Uani 0.473(7) 1 d D . P A 2
H5B1 H 0.3206 0.8630 0.6957 0.077 Uiso 0.473(7) 1 calc R U P A 2
H5B2 H 0.3840 0.8594 0.6249 0.077 Uiso 0.473(7) 1 calc R U P A 2
H5B3 H 0.3043 0.8522 0.5905 0.077 Uiso 0.473(7) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sn1 P1 2.6460(6) 3_656 ?
Sn1 P1 2.6460(6) . ?
Sn1 H100 0.8908 . ?
P1 C2 1.883(2) . ?
P1 C2 1.883(2) 10_557 ?
P1 B1 1.954(4) . ?
N1 C1 1.448(4) . ?
N1 C1 1.448(4) 12_655 ?
N1 Li1 2.097(5) . ?
N1 H1 0.83(5) . ?
B1 Li1 2.442(5) . ?
B1 H11 1.11(2) . ?
B1 H12 1.04(5) . ?
Li1 N1 2.097(5) 10_557 ?
Li1 B1 2.442(5) 3_656 ?
Li1 H1 2.33(5) . ?
Li1 H11 2.02(2) . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C2 C4B 1.428(5) . ?
C2 C5A 1.476(7) . ?
C2 C3A 1.522(5) . ?
C2 C5B 1.564(6) . ?
C2 C3B 1.636(5) . ?
C2 C4A 1.652(5) . ?
C3A H31A 0.9800 . ?
C3A H32A 0.9800 . ?
C3A H33A 0.9800 . ?
C4A H41A 0.9800 . ?
C4A H42A 0.9800 . ?
C4A H43A 0.9800 . ?
C5A H51A 0.9800 . ?
C5A H52A 0.9800 . ?
C5A H53A 0.9800 . ?
C3B H3B1 0.9800 . ?
C3B H3B2 0.9800 . ?
C3B H3B3 0.9800 . ?
C4B H4B1 0.9800 . ?
C4B H4B2 0.9800 . ?
C4B H4B3 0.9800 . ?
C5B H5B1 0.9800 . ?
C5B H5B2 0.9800 . ?
C5B H5B3 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
P1 Sn1 P1 104.98(3) 3_656 . ?
P1 Sn1 H100 73.9 3_656 . ?
P1 Sn1 H100 73.9 . . ?
C2 P1 C2 110.76(17) . 10_557 ?
C2 P1 B1 107.30(10) . . ?
C2 P1 B1 107.30(10) 10_557 . ?
C2 P1 Sn1 104.32(7) . . ?
C2 P1 Sn1 104.32(7) 10_557 . ?
B1 P1 Sn1 122.62(12) . . ?
C1 N1 C1 112.8(4) . 12_655 ?
C1 N1 Li1 114.8(2) . . ?
C1 N1 Li1 114.8(2) 12_655 . ?
C1 N1 H1 108.4(18) . . ?
C1 N1 H1 108.4(18) 12_655 . ?
Li1 N1 H1 96(4) . . ?
P1 B1 Li1 132.6(2) . . ?
P1 B1 H11 106.3(13) . . ?
Li1 B1 H11 54.8(12) . . ?
P1 B1 H12 111(3) . . ?
Li1 B1 H12 117(3) . . ?
H11 B1 H12 113.1(18) . . ?
N1 Li1 N1 110.3(4) 10_557 . ?
N1 Li1 B1 110.43(7) 10_557 . ?
N1 Li1 B1 110.43(7) . . ?
N1 Li1 B1 110.43(7) 10_557 3_656 ?
N1 Li1 B1 110.43(7) . 3_656 ?
B1 Li1 B1 104.6(3) . 3_656 ?
N1 Li1 H1 131.1(14) 10_557 . ?
N1 Li1 H1 20.8(12) . . ?
B1 Li1 H1 98.5(8) . . ?
B1 Li1 H1 98.5(8) 3_656 . ?
N1 Li1 H11 135.4(7) 10_557 . ?
N1 Li1 H11 89.1(7) . . ?
B1 Li1 H11 26.8(7) . . ?
B1 Li1 H11 98.5(7) 3_656 . ?
H1 Li1 H11 73.6(11) . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C1 H1D 109.5 . . ?
H1B C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?
C5A C2 C3A 116.0(4) . . ?
C4B C2 C5B 112.8(5) . . ?
C4B C2 C3B 108.9(4) . . ?
C5B C2 C3B 101.2(4) . . ?
C5A C2 C4A 106.8(5) . . ?
C3A C2 C4A 102.0(3) . . ?
C4B C2 P1 115.2(3) . . ?
C5A C2 P1 119.3(5) . . ?
C3A C2 P1 111.3(3) . . ?
C5B C2 P1 109.0(5) . . ?
C3B C2 P1 108.7(2) . . ?
C4A C2 P1 98.0(2) . . ?
C2 C3A H31A 109.5 . . ?
C2 C3A H32A 109.5 . . ?
H31A C3A H32A 109.5 . . ?
C2 C3A H33A 109.5 . . ?
H31A C3A H33A 109.5 . . ?
H32A C3A H33A 109.5 . . ?
C2 C4A H41A 109.5 . . ?
C2 C4A H42A 109.5 . . ?
H41A C4A H42A 109.5 . . ?
C2 C4A H43A 109.5 . . ?
H41A C4A H43A 109.5 . . ?
H42A C4A H43A 109.5 . . ?
C2 C5A H51A 109.5 . . ?
C2 C5A H52A 109.5 . . ?
H51A C5A H52A 109.5 . . ?
C2 C5A H53A 109.5 . . ?
H51A C5A H53A 109.5 . . ?
H52A C5A H53A 109.5 . . ?
C2 C3B H3B1 109.5 . . ?
C2 C3B H3B2 109.5 . . ?
H3B1 C3B H3B2 109.5 . . ?
C2 C3B H3B3 109.5 . . ?
H3B1 C3B H3B3 109.5 . . ?
H3B2 C3B H3B3 109.5 . . ?
C2 C4B H4B1 109.5 . . ?
C2 C4B H4B2 109.5 . . ?
H4B1 C4B H4B2 109.5 . . ?
C2 C4B H4B3 109.5 . . ?
H4B1 C4B H4B3 109.5 . . ?
H4B2 C4B H4B3 109.5 . . ?
C2 C5B H5B1 109.5 . . ?
C2 C5B H5B2 109.5 . . ?
H5B1 C5B H5B2 109.5 . . ?
C2 C5B H5B3 109.5 . . ?
H5B1 C5B H5B3 109.5 . . ?
H5B2 C5B H5B3 109.5 . . ?

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
C2 P1 C2 C4B -163.8(4) 10_557 . . . ?
B1 P1 C2 C4B -46.9(4) . . . . ?
Sn1 P1 C2 C4B 84.5(4) . . . . ?
C2 P1 C2 C5A 55.5(5) 10_557 . . . ?
B1 P1 C2 C5A 172.3(5) . . . . ?
Sn1 P1 C2 C5A -56.2(5) . . . . ?
C2 P1 C2 C3A -83.9(3) 10_557 . . . ?
B1 P1 C2 C3A 32.9(3) . . . . ?
Sn1 P1 C2 C3A 164.4(3) . . . . ?
C2 P1 C2 C5B 68.3(4) 10_557 . . . ?
B1 P1 C2 C5B -174.9(4) . . . . ?
Sn1 P1 C2 C5B -43.4(4) . . . . ?
C2 P1 C2 C3B -41.2(3) 10_557 . . . ?
B1 P1 C2 C3B 75.6(3) . . . . ?
Sn1 P1 C2 C3B -152.9(3) . . . . ?
C2 P1 C2 C4A 169.9(2) 10_557 . . . ?
B1 P1 C2 C4A -73.3(3) . . . . ?
Sn1 P1 C2 C4A 58.2(3) . . . . ?


_chemical_properties_physical    Air-sensitive
