# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_apx1807a
_database_code_depnum_ccdc_archive 'CCDC 1062520'
_audit_update_record             
;
2015-07-03 deposited with the CCDC.
2015-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H30 O Sn'
_chemical_formula_weight         369.10

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'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P nma'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   14.226(3)
_cell_length_b                   17.792(4)
_cell_length_c                   6.7620(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1711.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(1)
_cell_measurement_reflns_used    9972
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      28.53

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    1.486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6642
_exptl_absorpt_correction_T_max  0.8656
_exptl_absorpt_process_details   'SADABS v. 2.03 (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 with APEXII CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18503
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_sigmaI/netI    0.0098
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         28.60
_reflns_number_total             2160
_reflns_number_gt                2076
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II, v. 7.0 (Bruker AXS, 2009)'
_computing_cell_refinement       'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_publication_material  'SHELXTL, v. 6.14, (Bruker AXS, 2000)'

_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)+(0.0145P)²+1.0327P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2160
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0139
_refine_ls_R_factor_gt           0.0132
_refine_ls_wR_factor_ref         0.0344
_refine_ls_wR_factor_gt          0.0340
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn -0.071525(7) 0.7500 0.014086(15) 0.01127(4) Uani 1 2 d S . .
O1 O 0.06450(7) 0.7500 0.10333(17) 0.0124(2) Uani 1 2 d S . .
C1 C -0.07886(9) 0.65366(7) -0.17175(19) 0.0214(3) Uani 1 1 d . . .
H1A H -0.0196 0.6467 -0.2373 0.032 Uiso 1 1 calc R . .
H1B H -0.1274 0.6607 -0.2686 0.032 Uiso 1 1 calc R . .
H1C H -0.0928 0.6101 -0.0932 0.032 Uiso 1 1 calc R . .
C2 C -0.14210(12) 0.7500 0.2911(2) 0.0183(3) Uani 1 2 d S . .
H2A H -0.1630 0.7000 0.3211 0.028 Uiso 0.50 1 calc PR . .
H2B H -0.1953 0.7831 0.2848 0.028 Uiso 0.50 1 calc PR . .
H2C H -0.0998 0.7669 0.3924 0.028 Uiso 0.50 1 calc PR . .
C3 C 0.10668(10) 0.7500 0.2827(2) 0.0105(3) Uani 1 2 d S . .
C4 C 0.13212(7) 0.68053(6) 0.37323(16) 0.0113(2) Uani 1 1 d . . .
C5 C 0.17205(8) 0.68306(6) 0.56198(17) 0.0145(2) Uani 1 1 d . . .
H5 H 0.1870 0.6381 0.6249 0.017 Uiso 1 1 calc R . .
C6 C 0.19007(11) 0.7500 0.6582(2) 0.0157(3) Uani 1 2 d S . .
H6 H 0.2140 0.7500 0.7861 0.019 Uiso 1 2 calc SR . .
C7 C 0.11800(8) 0.60314(6) 0.27484(17) 0.0135(2) Uani 1 1 d . . .
C8 C 0.17509(9) 0.54146(7) 0.3797(2) 0.0229(3) Uani 1 1 d . . .
H8A H 0.2401 0.5557 0.3837 0.034 Uiso 1 1 calc R . .
H8B H 0.1687 0.4950 0.3087 0.034 Uiso 1 1 calc R . .
H8C H 0.1521 0.5351 0.5121 0.034 Uiso 1 1 calc R . .
C9 C 0.01405(8) 0.57991(7) 0.28822(18) 0.0179(2) Uani 1 1 d . . .
H9A H -0.0040 0.5759 0.4246 0.027 Uiso 1 1 calc R . .
H9B H 0.0055 0.5322 0.2243 0.027 Uiso 1 1 calc R . .
H9C H -0.0242 0.6171 0.2241 0.027 Uiso 1 1 calc R . .
C10 C 0.15147(9) 0.60279(7) 0.05820(18) 0.0179(2) Uani 1 1 d . . .
H10A H 0.1190 0.6413 -0.0142 0.027 Uiso 1 1 calc R . .
H10B H 0.1384 0.5547 0.0000 0.027 Uiso 1 1 calc R . .
H10C H 0.2179 0.6122 0.0537 0.027 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
Sn1 O1 2.0270(11) . ?
Sn1 C2 2.1251(17) . ?
Sn1 C1 2.1279(13) . ?
Sn1 C1 2.1279(13) 7_575 ?
O1 C3 1.3531(19) . ?
C3 C4 1.4260(13) 7_575 ?
C3 C4 1.4260(13) . ?
C4 C5 1.3978(16) . ?
C4 C7 1.5423(15) . ?
C5 C6 1.3811(14) . ?
C6 C5 1.3811(14) 7_575 ?
C7 C10 1.5403(16) . ?
C7 C9 1.5381(16) . ?
C7 C8 1.5384(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Sn1 C2 100.87(6) . . ?
O1 Sn1 C1 102.86(4) . . ?
C2 Sn1 C1 119.82(4) . . ?
O1 Sn1 C1 102.86(4) . 7_575 ?
C2 Sn1 C1 119.82(4) . 7_575 ?
C1 Sn1 C1 107.32(8) . 7_575 ?
C3 O1 Sn1 133.64(9) . . ?
O1 C3 C4 119.83(7) . 7_575 ?
O1 C3 C4 119.82(7) . . ?
C4 C3 C4 120.17(14) 7_575 . ?
C5 C4 C3 117.86(10) . . ?
C5 C4 C7 118.39(9) . . ?
C3 C4 C7 123.75(10) . . ?
C6 C5 C4 122.23(11) . . ?
C5 C6 C5 119.17(15) 7_575 . ?
C10 C7 C9 110.61(9) . . ?
C10 C7 C8 105.80(10) . . ?
C9 C7 C8 106.78(9) . . ?
C10 C7 C4 111.94(9) . . ?
C9 C7 C4 109.86(9) . . ?
C8 C7 C4 111.67(9) . . ?

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.051
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0

####################################################################### 
# 
# 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_apx1873
_database_code_depnum_ccdc_archive 'CCDC 1062521'
_audit_update_record             
;
2015-07-03 deposited with the CCDC.
2015-08-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT094_apx1873             
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       5.92 Report
RESPONSE: Small unresolved twin component
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H26 O Sn'
_chemical_formula_weight         341.05

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'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   19.588(6)
_cell_length_b                   6.6588(19)
_cell_length_c                   13.866(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.618(3)
_cell_angle_gamma                90.00
_cell_volume                     1657.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(1)
_cell_measurement_reflns_used    6013
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      28.44

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    1.528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5943
_exptl_absorpt_correction_T_max  0.8875
_exptl_absorpt_process_details   'SADABS v. 2.03 (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 with APEXII CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8800
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         28.44
_reflns_number_total             3816
_reflns_number_gt                3618
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II, v. 7.0 (Bruker AXS, 2009)'
_computing_cell_refinement       'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_publication_material  'SHELXTL, v. 6.14, (Bruker AXS, 2000)'

_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)+(0.0512P)²+0.3891P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_number_reflns         3816
_refine_ls_number_parameters     161
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0286
_refine_ls_wR_factor_ref         0.0719
_refine_ls_wR_factor_gt          0.0700
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.003
_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
Sn1 Sn 0.19925(5) 0.239251(19) 1.06256(6) 0.01608(7) Uani 1 1 d . . .
C1 C 0.1005(2) 0.0648(6) 1.0167(3) 0.0287(8) Uani 1 1 d . . .
H1A H 0.0580 0.1523 0.9961 0.043 Uiso 1 1 calc R . .
H1B H 0.1024 -0.0170 1.0747 0.043 Uiso 1 1 calc R . .
H1C H 0.0963 -0.0197 0.9585 0.043 Uiso 1 1 calc R . .
C3 C 0.2989(2) 0.0691(7) 1.1365(3) 0.0316(9) Uani 1 1 d . . .
H3A H 0.3078 -0.0089 1.0845 0.047 Uiso 1 1 calc R . .
H3B H 0.2937 -0.0190 1.1880 0.047 Uiso 1 1 calc R . .
H3C H 0.3400 0.1585 1.1704 0.047 Uiso 1 1 calc R . .
O1 O 0.20382(13) 0.2982(4) 0.92150(18) 0.0190(4) Uani 1 1 d . . .
C4 C 0.19882(16) 0.4899(4) 0.8846(2) 0.0163(5) Uani 1 1 d . . .
C5 C 0.26499(16) 0.5973(4) 0.9051(2) 0.0177(6) Uani 1 1 d . . .
C9 C 0.12919(17) 0.5734(5) 0.8243(2) 0.0213(6) Uani 1 1 d . . .
C8 C 0.1262(3) 0.7677(5) 0.7844(3) 0.0282(9) Uani 1 1 d . . .
H8 H 0.0803 0.8241 0.7432 0.034 Uiso 1 1 calc R . .
C6 C 0.2591(2) 0.7922(5) 0.8639(3) 0.0245(7) Uani 1 1 d . . .
H6 H 0.3022 0.8655 0.8761 0.029 Uiso 1 1 calc R . .
C7 C 0.1907(2) 0.8769(5) 0.8055(2) 0.0279(7) Uani 1 1 d . . .
H7 H 0.1879 1.0075 0.7804 0.033 Uiso 1 1 calc R . .
C10 C 0.33963(17) 0.5001(5) 0.9681(3) 0.0253(6) Uani 1 1 d . . .
H10 H 0.3333 0.4174 1.0224 0.030 Uiso 1 1 calc R . .
C14 C 0.0225(2) 0.3900(7) 0.6853(3) 0.0457(11) Uani 1 1 d . . .
H14A H -0.0196 0.3052 0.6744 0.069 Uiso 1 1 calc R . .
H14B H 0.0581 0.3181 0.6671 0.069 Uiso 1 1 calc R . .
H14C H 0.0063 0.5075 0.6419 0.069 Uiso 1 1 calc R . .
C13 C 0.05843(19) 0.4524(6) 0.8005(3) 0.0333(8) Uani 1 1 d . . .
H13 H 0.0727 0.3291 0.8425 0.040 Uiso 1 1 calc R . .
C11 C 0.3617(2) 0.3595(7) 0.8989(3) 0.0470(10) Uani 1 1 d . . .
H11A H 0.3230 0.2619 0.8673 0.070 Uiso 1 1 calc R . .
H11B H 0.4073 0.2922 0.9411 0.070 Uiso 1 1 calc R . .
H11C H 0.3686 0.4356 0.8448 0.070 Uiso 1 1 calc R . .
C12 C 0.4022(2) 0.6482(8) 1.0245(4) 0.0519(12) Uani 1 1 d . . .
H12A H 0.4105 0.7312 0.9736 0.078 Uiso 1 1 calc R . .
H12B H 0.4470 0.5757 1.0648 0.078 Uiso 1 1 calc R . .
H12C H 0.3886 0.7310 1.0707 0.078 Uiso 1 1 calc R . .
C2 C 0.1993(2) 0.5349(5) 1.1190(3) 0.0284(7) Uani 1 1 d . . .
H2A H 0.2417 0.6066 1.1187 0.043 Uiso 1 1 calc R . .
H2B H 0.2017 0.5295 1.1894 0.043 Uiso 1 1 calc R . .
H2C H 0.1545 0.6026 1.0743 0.043 Uiso 1 1 calc R . .
C15 C 0.0021(2) 0.5612(10) 0.8317(4) 0.0645(15) Uani 1 1 d . . .
H15A H 0.0254 0.6007 0.9043 0.097 Uiso 1 1 calc R . .
H15B H -0.0390 0.4734 0.8221 0.097 Uiso 1 1 calc R . .
H15C H -0.0158 0.6784 0.7885 0.097 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
Sn1 O1 2.032(3) . ?
Sn1 C2 2.118(3) . ?
Sn1 C1 2.124(4) . ?
Sn1 C3 2.130(4) . ?
O1 C4 1.364(4) . ?
C4 C9 1.398(4) . ?
C4 C5 1.406(4) . ?
C5 C6 1.404(4) . ?
C5 C10 1.516(4) . ?
C9 C8 1.398(4) . ?
C9 C13 1.521(5) . ?
C8 C7 1.384(6) . ?
C6 C7 1.379(5) . ?
C10 C12 1.523(5) . ?
C10 C11 1.522(5) . ?
C14 C13 1.523(5) . ?
C13 C15 1.521(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Sn1 C2 100.49(12) . . ?
O1 Sn1 C1 101.74(13) . . ?
C2 Sn1 C1 118.98(16) . . ?
O1 Sn1 C3 100.43(13) . . ?
C2 Sn1 C3 116.85(17) . . ?
C1 Sn1 C3 113.71(13) . . ?
C4 O1 Sn1 121.19(18) . . ?
O1 C4 C9 120.2(3) . . ?
O1 C4 C5 118.6(3) . . ?
C9 C4 C5 121.2(3) . . ?
C6 C5 C4 118.0(3) . . ?
C6 C5 C10 122.2(3) . . ?
C4 C5 C10 119.8(3) . . ?
C4 C9 C8 118.7(3) . . ?
C4 C9 C13 120.3(3) . . ?
C8 C9 C13 120.9(3) . . ?
C7 C8 C9 120.8(4) . . ?
C7 C6 C5 121.3(3) . . ?
C6 C7 C8 120.0(3) . . ?
C5 C10 C12 114.3(3) . . ?
C5 C10 C11 110.6(3) . . ?
C12 C10 C11 110.4(3) . . ?
C9 C13 C15 112.9(3) . . ?
C9 C13 C14 111.7(3) . . ?
C15 C13 C14 110.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.952
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         3.275
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.108
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0

####################################################################### 
# 
# 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_apx1996_p21
_database_code_depnum_ccdc_archive 'CCDC 1062522'
_audit_update_record             
;
2015-08-05 deposited with the CCDC.
2015-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H39 N Sn'
_chemical_formula_weight         424.22

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'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.0759(19)
_cell_length_b                   18.516(6)
_cell_length_c                   10.153(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.675(3)
_cell_angle_gamma                90.00
_cell_volume                     1099.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(1)
_cell_measurement_reflns_used    9598
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      28.47

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             444
_exptl_absorpt_coefficient_mu    1.163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8180
_exptl_absorpt_correction_T_max  0.9127
_exptl_absorpt_process_details   'SADABS v. 2.03 (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 with APEXII CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12739
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         28.59
_reflns_number_total             5187
_reflns_number_gt                5072
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II, v. 7.0 (Bruker AXS, 2009)'
_computing_cell_refinement       'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_publication_material  'SHELXTL, v. 6.14, (Bruker AXS, 2000)'

_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)+(0.0179P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.050(13)
_refine_ls_number_reflns         5187
_refine_ls_number_parameters     220
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0180
_refine_ls_R_factor_gt           0.0173
_refine_ls_wR_factor_ref         0.0412
_refine_ls_wR_factor_gt          0.0408
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.129
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn 0.746756(16) 0.311100(9) 0.398300(10) 0.01840(4) Uani 1 1 d . . .
N1 N 0.5760(3) 0.40074(11) 0.3048(2) 0.0172(4) Uani 1 1 d . . .
H1 H 0.4339 0.4041 0.3026 0.021 Uiso 1 1 calc R . .
C1 C 0.6692(3) 0.45800(9) 0.24309(18) 0.0129(3) Uani 1 1 d . . .
C2 C 0.6442(3) 0.45906(9) 0.09921(17) 0.0120(3) Uani 1 1 d . . .
C3 C 0.7586(3) 0.51306(9) 0.04705(17) 0.0130(3) Uani 1 1 d . . .
H3 H 0.7441 0.5135 -0.0465 0.016 Uiso 1 1 calc R . .
C4 C 0.8910(3) 0.56544(9) 0.12654(17) 0.0123(3) Uani 1 1 d . . .
C5 C 0.8954(3) 0.56678(9) 0.26470(18) 0.0140(3) Uani 1 1 d . . .
H5 H 0.9778 0.6032 0.3195 0.017 Uiso 1 1 calc R . .
C6 C 0.7826(3) 0.51621(9) 0.32457(17) 0.0133(3) Uani 1 1 d . . .
C7 C 0.5020(3) 0.40374(10) -0.00213(18) 0.0155(3) Uani 1 1 d . . .
C8 C 0.6272(4) 0.33139(9) 0.0106(2) 0.0229(4) Uani 1 1 d . . .
H8A H 0.5376 0.2978 -0.0540 0.034 Uiso 1 1 calc R . .
H8B H 0.6501 0.3129 0.1016 0.034 Uiso 1 1 calc R . .
H8C H 0.7727 0.3381 -0.0079 0.034 Uiso 1 1 calc R . .
C9 C 0.2598(3) 0.39373(12) 0.0153(2) 0.0254(4) Uani 1 1 d . . .
H9A H 0.1578 0.3792 -0.0704 0.038 Uiso 1 1 calc R . .
H9B H 0.2080 0.4385 0.0440 0.038 Uiso 1 1 calc R . .
H9C H 0.2627 0.3573 0.0829 0.038 Uiso 1 1 calc R . .
C10 C 0.4661(4) 0.42840(12) -0.1514(2) 0.0265(4) Uani 1 1 d . . .
H10A H 0.6106 0.4294 -0.1728 0.040 Uiso 1 1 calc R . .
H10B H 0.3999 0.4758 -0.1628 0.040 Uiso 1 1 calc R . .
H10C H 0.3654 0.3953 -0.2116 0.040 Uiso 1 1 calc R . .
C11 C 1.0150(3) 0.62468(9) 0.06853(18) 0.0154(3) Uani 1 1 d . . .
C12 C 1.0023(4) 0.61168(11) -0.08181(19) 0.0264(4) Uani 1 1 d . . .
H12A H 0.8454 0.6121 -0.1348 0.040 Uiso 1 1 calc R . .
H12B H 1.0692 0.5657 -0.0914 0.040 Uiso 1 1 calc R . .
H12C H 1.0844 0.6491 -0.1137 0.040 Uiso 1 1 calc R . .
C13 C 0.8982(3) 0.69696(10) 0.0788(2) 0.0229(4) Uani 1 1 d . . .
H13A H 0.9731 0.7347 0.0425 0.034 Uiso 1 1 calc R . .
H13B H 0.9077 0.7070 0.1729 0.034 Uiso 1 1 calc R . .
H13C H 0.7405 0.6945 0.0275 0.034 Uiso 1 1 calc R . .
C14 C 1.2675(3) 0.62848(11) 0.1500(2) 0.0215(4) Uani 1 1 d . . .
H14A H 1.3406 0.5833 0.1424 0.032 Uiso 1 1 calc R . .
H14B H 1.2780 0.6380 0.2444 0.032 Uiso 1 1 calc R . .
H14C H 1.3419 0.6665 0.1141 0.032 Uiso 1 1 calc R . .
C15 C 0.7818(3) 0.52989(10) 0.47531(18) 0.0170(4) Uani 1 1 d . . .
C16 C 0.8454(4) 0.60869(12) 0.5175(2) 0.0302(5) Uani 1 1 d . . .
H16A H 0.8284 0.6170 0.6075 0.045 Uiso 1 1 calc R . .
H16B H 0.7463 0.6407 0.4538 0.045 Uiso 1 1 calc R . .
H16C H 1.0011 0.6175 0.5174 0.045 Uiso 1 1 calc R . .
C17 C 0.5432(3) 0.51816(12) 0.4978(2) 0.0251(4) Uani 1 1 d . . .
H17A H 0.5030 0.4680 0.4855 0.038 Uiso 1 1 calc R . .
H17B H 0.4326 0.5465 0.4329 0.038 Uiso 1 1 calc R . .
H17C H 0.5455 0.5327 0.5889 0.038 Uiso 1 1 calc R . .
C18 C 0.9575(3) 0.48219(12) 0.57358(19) 0.0238(4) Uani 1 1 d . . .
H18A H 1.1058 0.4901 0.5597 0.036 Uiso 1 1 calc R . .
H18B H 0.9157 0.4324 0.5565 0.036 Uiso 1 1 calc R . .
H18C H 0.9612 0.4941 0.6662 0.036 Uiso 1 1 calc R . .
C19 C 0.5716(5) 0.21738(13) 0.2979(3) 0.0265(6) Uani 1 1 d . . .
H19A H 0.4277 0.2315 0.2372 0.040 Uiso 1 1 calc R . .
H19B H 0.5456 0.1844 0.3650 0.040 Uiso 1 1 calc R . .
H19C H 0.6632 0.1943 0.2465 0.040 Uiso 1 1 calc R . .
C20 C 0.7226(3) 0.3069(3) 0.60432(18) 0.0352(5) Uani 1 1 d . . .
H20A H 0.6092 0.3407 0.6155 0.053 Uiso 1 1 calc R . .
H20B H 0.8679 0.3191 0.6658 0.053 Uiso 1 1 calc R . .
H20C H 0.6799 0.2590 0.6242 0.053 Uiso 1 1 calc R . .
C21 C 1.0864(3) 0.32009(16) 0.3791(2) 0.0349(6) Uani 1 1 d . . .
H21A H 1.0921 0.3015 0.2918 0.052 Uiso 1 1 calc R . .
H21B H 1.1884 0.2929 0.4506 0.052 Uiso 1 1 calc R . .
H21C H 1.1318 0.3699 0.3863 0.052 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
Sn1 N1 2.050(2) . ?
Sn1 C21 2.131(2) . ?
Sn1 C20 2.1375(19) . ?
Sn1 C19 2.144(3) . ?
N1 C1 1.424(2) . ?
C1 C6 1.419(2) . ?
C1 C2 1.427(2) . ?
C2 C3 1.401(2) . ?
C2 C7 1.541(2) . ?
C3 C4 1.374(2) . ?
C4 C5 1.396(2) . ?
C4 C11 1.535(2) . ?
C5 C6 1.393(2) . ?
C6 C15 1.553(2) . ?
C7 C8 1.529(2) . ?
C7 C9 1.540(3) . ?
C7 C10 1.541(3) . ?
C11 C12 1.527(3) . ?
C11 C13 1.532(2) . ?
C11 C14 1.536(3) . ?
C15 C18 1.529(3) . ?
C15 C16 1.540(3) . ?
C15 C17 1.543(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Sn1 C21 106.01(10) . . ?
N1 Sn1 C20 108.83(14) . . ?
C21 Sn1 C20 114.61(8) . . ?
N1 Sn1 C19 108.13(7) . . ?
C21 Sn1 C19 112.84(11) . . ?
C20 Sn1 C19 106.23(14) . . ?
C1 N1 Sn1 126.50(14) . . ?
C6 C1 N1 119.81(16) . . ?
C6 C1 C2 119.14(15) . . ?
N1 C1 C2 121.02(16) . . ?
C3 C2 C1 118.06(15) . . ?
C3 C2 C7 117.90(15) . . ?
C1 C2 C7 124.03(15) . . ?
C4 C3 C2 123.59(16) . . ?
C3 C4 C5 116.88(15) . . ?
C3 C4 C11 123.29(15) . . ?
C5 C4 C11 119.64(15) . . ?
C6 C5 C4 123.24(16) . . ?
C5 C6 C1 118.34(15) . . ?
C5 C6 C15 116.95(15) . . ?
C1 C6 C15 124.65(15) . . ?
C8 C7 C9 110.74(15) . . ?
C8 C7 C10 106.12(15) . . ?
C9 C7 C10 105.22(16) . . ?
C8 C7 C2 110.46(15) . . ?
C9 C7 C2 112.60(15) . . ?
C10 C7 C2 111.39(15) . . ?
C12 C11 C13 107.87(16) . . ?
C12 C11 C4 111.94(15) . . ?
C13 C11 C4 108.28(14) . . ?
C12 C11 C14 108.60(15) . . ?
C13 C11 C14 109.70(15) . . ?
C4 C11 C14 110.41(15) . . ?
C18 C15 C16 106.70(16) . . ?
C18 C15 C17 109.90(16) . . ?
C16 C15 C17 105.50(16) . . ?
C18 C15 C6 111.20(15) . . ?
C16 C15 C6 111.18(15) . . ?
C17 C15 C6 112.08(15) . . ?

_diffrn_measured_fraction_theta_max 0.949
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.048
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0

