# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2007

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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data_arc1447
_database_code_depnum_ccdc_archive 'CCDC 632847'
#=============================================================
# Diffractometer details
#=============================================================
_diffrn_measurement_device_type  
;
Nonius KappaCCD
;
_diffrn_radiation_monochromator  graphite
_computing_data_collection       
;
KappaCCD software 'Collect' (Nonius, 2000)
;
_computing_data_reduction        
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_cell_refinement       
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
#=============================================================
# General computing
#=============================================================
_computing_structure_refinement  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_publication_material  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'


_chemical_name_systematic        # IUPAC name, in full
;
?
;
_chemical_melting_point          ?
_exptl_crystal_thermal_history   
;
The material was crystallised at ambient temperature. A suitable crystal
was cooled rapidly to 150K for single-crystal X-ray diffraction analysis.
;
_refine_ls_matrix_type           full
_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_special_details          
;
The hydrogen atoms of the permethylpentalene were located in a difference
Fourier map and their coordinates and isotropic displacement parameters
subsequently refined, subject to restraint of the C-H distances to 1.00(5) \%A
and of the C-C-H and H-C-H angles to 109(4) \%. Other hydrogen atoms were
positioned geometrically.
;
#=============================================================

_cell_length_a                   7.8927(2)
_cell_angle_alpha                99.4761(7)
_cell_length_b                   10.0097(2)
_cell_angle_beta                 101.8991(7)
_cell_length_c                   14.9792(3)
_cell_angle_gamma                102.8466(7)
_cell_volume                     1101.18(4)

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1 '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 International_Tables_Vol_IV_Table_2.2B
'Sn ' -0.6537 1.4246 19.1889 5.8303 19.1005 0.5031 4.4585 26.8909 2.4663
83.9572 4.7821 International_Tables_Vol_IV_Table_2.2B


_cell_formula_units_Z            2
_chemical_formula_sum            ' C20 H36 Sn2 '
_chemical_formula_moiety         ' C20 H36 Sn2 '
_chemical_compound_source        
;
synthesis as described
;
_chemical_formula_weight         513.89


_cell_measurement_reflns_used    16301
_cell_measurement_theta_min      5
_cell_measurement_theta_max      28
_cell_measurement_temperature    150

_exptl_crystal_description       ' prism '
_exptl_crystal_colour            ' pale yellow '
_exptl_crystal_size_min          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_max          0.24

_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    2.265

_diffrn_measurement_method       \w

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_absorpt_correction_T_min  0.58
_exptl_absorpt_correction_T_max  0.67

_diffrn_standards_interval_time  0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0.00

_diffrn_ambient_temperature      150
_diffrn_reflns_number            16301
_reflns_number_total             5011
_diffrn_reflns_av_R_equivalents  0.024

_diffrn_reflns_theta_min         5.129
_diffrn_reflns_theta_max         27.532
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        27.532
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_reflns_limit_h_min              -10
_reflns_limit_h_max              9
_reflns_limit_k_min              -12
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              19


_refine_diff_density_min         -0.78
_refine_diff_density_max         0.88


_refine_ls_number_reflns         4143
_refine_ls_number_restraints     54
_refine_ls_number_parameters     271

#_refine_ls_R_factor_ref 0.0246
_refine_ls_wR_factor_ref         0.0290
_refine_ls_goodness_of_fit_ref   1.0405

#_reflns_number_all 5011
_refine_ls_R_factor_all          0.0315
_refine_ls_wR_factor_all         0.0349

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>3.00u(I)
_reflns_number_gt                4143
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_gt          0.0290


_refine_ls_shift/su_max          0.036881
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
0.505 0.212 0.263
;
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073

# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
Sn1 Sn 0.42387(2) 0.484293(17) 0.179292(11) 0.0221 1.0000 Uani .
Sn2 Sn 0.17418(2) 0.093646(17) 0.343309(12) 0.0234 1.0000 Uani .
C1 C 0.5902(3) 0.3330(3) 0.18526(17) 0.0218 1.0000 Uani D
C2 C 0.7091(3) 0.3855(3) 0.28326(18) 0.0226 1.0000 Uani D
C3 C 0.6558(3) 0.2975(3) 0.33925(17) 0.0211 1.0000 Uani D
C4 C 0.5101(3) 0.1816(3) 0.28159(18) 0.0214 1.0000 Uani .
C5 C 0.3968(3) 0.0443(3) 0.28707(19) 0.0245 1.0000 Uani D
C6 C 0.3049(4) -0.0216(3) 0.18563(19) 0.0265 1.0000 Uani D
C7 C 0.3464(3) 0.0706(3) 0.13040(18) 0.0245 1.0000 Uani D
C8 C 0.4738(3) 0.1975(3) 0.19078(17) 0.0216 1.0000 Uani .
C9 C 0.6828(4) 0.3316(3) 0.1050(2) 0.0298 1.0000 Uani D
C10 C 0.8589(4) 0.5178(3) 0.3129(2) 0.0328 1.0000 Uani D
C11 C 0.7395(4) 0.3165(3) 0.4417(2) 0.0338 1.0000 Uani D
C12 C 0.4889(4) -0.0440(3) 0.3451(2) 0.0349 1.0000 Uani D
C13 C 0.1754(4) -0.1655(3) 0.1541(2) 0.0376 1.0000 Uani D
C14 C 0.2738(4) 0.0473(3) 0.0267(2) 0.0351 1.0000 Uani D
C15 C 0.5839(4) 0.6744(3) 0.1568(2) 0.0369 1.0000 Uani .
C16 C 0.3541(4) 0.5250(3) 0.3096(2) 0.0322 1.0000 Uani .
C17 C 0.1828(4) 0.4086(3) 0.0675(2) 0.0339 1.0000 Uani .
C18 C 0.0384(5) -0.0922(4) 0.3801(3) 0.0448 1.0000 Uani .
C19 C -0.0046(4) 0.1489(4) 0.2365(2) 0.0378 1.0000 Uani .
C20 C 0.2726(4) 0.2556(3) 0.4692(2) 0.0354 1.0000 Uani .
H91 H 0.598(4) 0.306(4) 0.047(2) 0.044(10) 1.0000 Uiso D
H92 H 0.763(5) 0.428(3) 0.108(2) 0.047(10) 1.0000 Uiso D
H93 H 0.756(4) 0.269(3) 0.109(2) 0.033(9) 1.0000 Uiso D
H101 H 0.956(5) 0.513(4) 0.364(3) 0.069(14) 1.0000 Uiso D
H102 H 0.912(5) 0.535(4) 0.259(2) 0.052(11) 1.0000 Uiso D
H103 H 0.814(5) 0.601(4) 0.334(3) 0.057(12) 1.0000 Uiso D
H111 H 0.648(5) 0.286(5) 0.475(3) 0.085(17) 1.0000 Uiso D
H112 H 0.827(6) 0.260(5) 0.451(3) 0.11(2) 1.0000 Uiso D
H113 H 0.800(6) 0.414(4) 0.470(3) 0.097(19) 1.0000 Uiso D
H121 H 0.408(4) -0.132(3) 0.342(2) 0.038(9) 1.0000 Uiso D
H122 H 0.540(4) 0.011(3) 0.412(2) 0.040(10) 1.0000 Uiso D
H123 H 0.588(5) -0.059(4) 0.321(2) 0.053(12) 1.0000 Uiso D
H131 H 0.177(5) -0.205(4) 0.091(3) 0.067(14) 1.0000 Uiso D
H132 H 0.212(5) -0.227(4) 0.195(3) 0.061(13) 1.0000 Uiso D
H133 H 0.052(5) -0.164(4) 0.155(3) 0.067(14) 1.0000 Uiso D
H141 H 0.214(6) 0.120(4) 0.008(3) 0.077(15) 1.0000 Uiso D
H142 H 0.371(5) 0.053(4) -0.006(3) 0.072(15) 1.0000 Uiso D
H143 H 0.191(5) -0.045(4) 0.003(3) 0.072(15) 1.0000 Uiso D
H151 H 0.5125 0.7452 0.1538 0.0459 1.0000 Uiso .
H152 H 0.6944 0.7128 0.2096 0.0459 1.0000 Uiso .
H153 H 0.6191 0.6533 0.0967 0.0459 1.0000 Uiso .
H161 H 0.2789 0.5933 0.3080 0.0397 1.0000 Uiso .
H162 H 0.4660 0.5655 0.3614 0.0397 1.0000 Uiso .
H163 H 0.2847 0.4352 0.3206 0.0397 1.0000 Uiso .
H171 H 0.1129 0.4806 0.0680 0.0400 1.0000 Uiso .
H172 H 0.2151 0.3908 0.0063 0.0400 1.0000 Uiso .
H173 H 0.1082 0.3193 0.0764 0.0400 1.0000 Uiso .
H181 H -0.0634 -0.0734 0.4059 0.0528 1.0000 Uiso .
H182 H 0.1245 -0.1190 0.4284 0.0528 1.0000 Uiso .
H183 H -0.0092 -0.1706 0.3232 0.0528 1.0000 Uiso .
H191 H -0.1062 0.1715 0.2608 0.0472 1.0000 Uiso .
H192 H 0.0617 0.2328 0.2178 0.0472 1.0000 Uiso .
H193 H -0.0530 0.0683 0.1810 0.0472 1.0000 Uiso .
H201 H 0.1689 0.2753 0.4927 0.0411 1.0000 Uiso .
H202 H 0.3521 0.2239 0.5177 0.0411 1.0000 Uiso .
H203 H 0.3425 0.3430 0.4557 0.0411 1.0000 Uiso .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Sn1 0.02032(9) 0.02517(10) 0.02207(9) 0.00637(7) 0.00506(7) 0.00828(7)
Sn2 0.02306(10) 0.02200(10) 0.02431(10) 0.00640(7) 0.00523(7) 0.00382(7)
C1 0.0198(11) 0.0258(12) 0.0204(11) 0.0036(9) 0.0038(9) 0.010(1)
C2 0.0173(11) 0.0242(12) 0.0239(12) 0.0031(9) 0.0013(9) 0.0060(9)
C3 0.0173(11) 0.0234(11) 0.0215(11) 0.0034(9) 0.0012(9) 0.0075(9)
C4 0.0199(11) 0.0212(11) 0.0236(12) 0.0036(9) 0.0043(9) 0.0083(9)
C5 0.0241(12) 0.0218(12) 0.0277(13) 0.0038(10) 0.0052(10) 0.0088(10)
C6 0.0248(12) 0.0207(12) 0.0291(13) -0.0039(10) 0.0005(10) 0.0087(10)
C7 0.0237(12) 0.0245(12) 0.0232(12) -0.0018(9) 0.0025(9) 0.0107(10)
C8 0.0204(11) 0.0228(12) 0.0204(11) 0.0012(9) 0.0021(9) 0.0085(9)
C9 0.0279(13) 0.0402(15) 0.0264(13) 0.0092(11) 0.0101(11) 0.0153(12)
C10 0.0221(13) 0.0345(15) 0.0342(15) 0.0075(12) -0.0005(11) -0.0007(11)
C11 0.0294(14) 0.0404(16) 0.0232(13) 0.0050(11) -0.0030(11) 0.0026(13)
C12 0.0356(15) 0.0284(14) 0.0422(17) 0.0135(13) 0.0037(13) 0.0133(12)
C13 0.0363(16) 0.0235(13) 0.0438(18) -0.0032(12) 0.0021(13) 0.0043(12)
C14 0.0368(15) 0.0371(16) 0.0228(13) -0.0036(11) -0.0022(11) 0.0093(13)
C15 0.0339(15) 0.0336(15) 0.0473(17) 0.0172(13) 0.0144(13) 0.0077(12)
C16 0.0388(15) 0.0345(14) 0.0259(13) 0.0051(11) 0.0130(12) 0.0117(12)
C17 0.0291(14) 0.0422(16) 0.0288(14) 0.0083(12) 0.0011(11) 0.0113(12)
C18 0.0434(18) 0.0353(16) 0.053(2) 0.0183(15) 0.0153(16) -0.0033(14)
C19 0.0342(15) 0.0490(18) 0.0347(15) 0.0103(13) 0.0058(12) 0.0223(14)
C20 0.0402(16) 0.0339(15) 0.0286(14) 0.0001(11) 0.0118(12) 0.0050(13)
_refine_ls_extinction_method     None
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Sn1 . C1 . 2.215(2) yes
Sn1 . C15 . 2.156(3) yes
Sn1 . C16 . 2.136(3) yes
Sn1 . C17 . 2.151(3) yes
Sn2 . C5 . 2.213(3) yes
Sn2 . C18 . 2.146(3) yes
Sn2 . C19 . 2.136(3) yes
Sn2 . C20 . 2.149(3) yes
C1 . C2 . 1.507(3) yes
C1 . C8 . 1.485(4) yes
C1 . C9 . 1.531(4) yes
C2 . C3 . 1.371(4) yes
C2 . C10 . 1.497(4) yes
C3 . C4 . 1.443(3) yes
C3 . C11 . 1.502(4) yes
C4 . C5 . 1.488(4) yes
C4 . C8 . 1.374(3) yes
C5 . C6 . 1.508(4) yes
C5 . C12 . 1.532(4) yes
C6 . C7 . 1.369(4) yes
C6 . C13 . 1.505(4) yes
C7 . C8 . 1.456(3) yes
C7 . C14 . 1.500(4) yes
C9 . H91 . 0.94(3) no
C9 . H92 . 1.02(3) no
C9 . H93 . 0.95(3) no
C10 . H101 . 0.98(4) no
C10 . H102 . 1.00(3) no
C10 . H103 . 1.01(3) no
C11 . H111 . 0.98(4) no
C11 . H112 . 0.98(4) no
C11 . H113 . 0.96(4) no
C12 . H121 . 0.95(3) no
C12 . H122 . 1.01(3) no
C12 . H123 . 0.96(3) no
C13 . H131 . 0.96(4) no
C13 . H132 . 0.98(3) no
C13 . H133 . 0.98(4) no
C14 . H141 . 1.00(4) no
C14 . H142 . 0.98(4) no
C14 . H143 . 0.97(4) no
C15 . H151 . 1.000 no
C15 . H152 . 1.000 no
C15 . H153 . 1.000 no
C16 . H161 . 1.000 no
C16 . H162 . 1.000 no
C16 . H163 . 1.000 no
C17 . H171 . 1.000 no
C17 . H172 . 1.000 no
C17 . H173 . 1.000 no
C18 . H181 . 1.000 no
C18 . H182 . 1.000 no
C18 . H183 . 1.000 no
C19 . H191 . 1.000 no
C19 . H192 . 1.000 no
C19 . H193 . 1.000 no
C20 . H201 . 1.000 no
C20 . H202 . 1.000 no
C20 . H203 . 1.000 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 . Sn1 . C15 . 107.41(11) yes
C1 . Sn1 . C16 . 108.58(10) yes
C15 . Sn1 . C16 . 110.26(12) yes
C1 . Sn1 . C17 . 112.70(11) yes
C15 . Sn1 . C17 . 108.59(12) yes
C16 . Sn1 . C17 . 109.28(12) yes
C5 . Sn2 . C18 . 107.39(13) yes
C5 . Sn2 . C19 . 108.42(11) yes
C18 . Sn2 . C19 . 110.20(14) yes
C5 . Sn2 . C20 . 111.50(11) yes
C18 . Sn2 . C20 . 106.93(13) yes
C19 . Sn2 . C20 . 112.30(13) yes
Sn1 . C1 . C2 . 101.65(15) yes
Sn1 . C1 . C8 . 107.31(16) yes
C2 . C1 . C8 . 102.4(2) yes
Sn1 . C1 . C9 . 109.58(17) yes
C2 . C1 . C9 . 117.1(2) yes
C8 . C1 . C9 . 117.3(2) yes
C1 . C2 . C3 . 110.1(2) yes
C1 . C2 . C10 . 123.4(2) yes
C3 . C2 . C10 . 126.5(2) yes
C2 . C3 . C4 . 107.9(2) yes
C2 . C3 . C11 . 125.8(2) yes
C4 . C3 . C11 . 126.3(2) yes
C3 . C4 . C5 . 140.2(2) yes
C3 . C4 . C8 . 109.9(2) yes
C5 . C4 . C8 . 109.6(2) yes
Sn2 . C5 . C4 . 105.73(16) yes
Sn2 . C5 . C6 . 102.45(17) yes
C4 . C5 . C6 . 102.2(2) yes
Sn2 . C5 . C12 . 110.1(2) yes
C4 . C5 . C12 . 117.1(2) yes
C6 . C5 . C12 . 117.6(2) yes
C5 . C6 . C7 . 110.6(2) yes
C5 . C6 . C13 . 122.7(3) yes
C7 . C6 . C13 . 126.5(3) yes
C6 . C7 . C8 . 107.5(2) yes
C6 . C7 . C14 . 126.7(3) yes
C8 . C7 . C14 . 125.7(3) yes
C1 . C8 . C4 . 109.4(2) yes
C1 . C8 . C7 . 140.6(2) yes
C4 . C8 . C7 . 109.7(2) yes
C1 . C9 . H91 . 111.0(20) no
C1 . C9 . H92 . 111.7(19) no
H91 . C9 . H92 . 107(2) no
C1 . C9 . H93 . 109.3(18) no
H91 . C9 . H93 . 111(2) no
H92 . C9 . H93 . 108(2) no
C2 . C10 . H101 . 112(2) no
C2 . C10 . H102 . 110(2) no
H101 . C10 . H102 . 108(3) no
C2 . C10 . H103 . 111(2) no
H101 . C10 . H103 . 108(3) no
H102 . C10 . H103 . 108(2) no
C3 . C11 . H111 . 111(2) no
C3 . C11 . H112 . 110(3) no
H111 . C11 . H112 . 108(3) no
C3 . C11 . H113 . 111(2) no
H111 . C11 . H113 . 107(3) no
H112 . C11 . H113 . 109(3) no
C5 . C12 . H121 . 111.6(19) no
C5 . C12 . H122 . 109.5(18) no
H121 . C12 . H122 . 111(2) no
C5 . C12 . H123 . 108(2) no
H121 . C12 . H123 . 110(2) no
H122 . C12 . H123 . 107(2) no
C6 . C13 . H131 . 109(2) no
C6 . C13 . H132 . 110(2) no
H131 . C13 . H132 . 109(3) no
C6 . C13 . H133 . 113(2) no
H131 . C13 . H133 . 109(3) no
H132 . C13 . H133 . 108(3) no
C7 . C14 . H141 . 114(2) no
C7 . C14 . H142 . 111(2) no
H141 . C14 . H142 . 104(3) no
C7 . C14 . H143 . 110(2) no
H141 . C14 . H143 . 109(3) no
H142 . C14 . H143 . 108(3) no
Sn1 . C15 . H151 . 109.466 no
Sn1 . C15 . H152 . 109.467 no
H151 . C15 . H152 . 109.476 no
Sn1 . C15 . H153 . 109.466 no
H151 . C15 . H153 . 109.475 no
H152 . C15 . H153 . 109.476 no
Sn1 . C16 . H161 . 109.466 no
Sn1 . C16 . H162 . 109.467 no
H161 . C16 . H162 . 109.476 no
Sn1 . C16 . H163 . 109.467 no
H161 . C16 . H163 . 109.476 no
H162 . C16 . H163 . 109.476 no
Sn1 . C17 . H171 . 109.467 no
Sn1 . C17 . H172 . 109.466 no
H171 . C17 . H172 . 109.476 no
Sn1 . C17 . H173 . 109.467 no
H171 . C17 . H173 . 109.476 no
H172 . C17 . H173 . 109.476 no
Sn2 . C18 . H181 . 109.466 no
Sn2 . C18 . H182 . 109.467 no
H181 . C18 . H182 . 109.475 no
Sn2 . C18 . H183 . 109.467 no
H181 . C18 . H183 . 109.476 no
H182 . C18 . H183 . 109.476 no
Sn2 . C19 . H191 . 109.466 no
Sn2 . C19 . H192 . 109.466 no
H191 . C19 . H192 . 109.476 no
Sn2 . C19 . H193 . 109.467 no
H191 . C19 . H193 . 109.476 no
H192 . C19 . H193 . 109.476 no
Sn2 . C20 . H201 . 109.467 no
Sn2 . C20 . H202 . 109.467 no
H201 . C20 . H202 . 109.476 no
Sn2 . C20 . H203 . 109.467 no
H201 . C20 . H203 . 109.476 no
H202 . C20 . H203 . 109.476 no


data_arc1441
_database_code_depnum_ccdc_archive 'CCDC 632848'
#=============================================================
# Diffractometer details
#=============================================================
_diffrn_measurement_device_type  
;
Nonius KappaCCD
;
_diffrn_radiation_monochromator  graphite
_computing_data_collection       
;
KappaCCD software 'Collect' (Nonius, 2000)
;
_computing_data_reduction        
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_cell_refinement       
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
#=============================================================
# General computing
#=============================================================
_computing_structure_refinement  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_publication_material  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'


_chemical_name_systematic        # IUPAC name, in full
;
?
;
_chemical_melting_point          ?
_exptl_crystal_thermal_history   
;
The material was crystallised at ambient temperature. A suitable crystal
was cooled rapidly to 150K for single-crystal X-ray diffraction analysis.
;
_refine_ls_matrix_type           full
_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_special_details          
;
The hydrogen atoms of the permethylpentalene were located in a difference
Fourier map and their coordinates and isotropic displacement parameters
subsequently refined, subject to restraint of the C-H distances to 1,00(5) \%A
and of the C-C-H and H-C-H angles to 109(4) \%. Other hydrogen atoms were
positioned geometrically.

The largest peaks of residual electron density lie close to the methylene C
atoms of the tetramethylethylenediamine, suggesting that this residue might
be disordered. Attempts to model this led to no improvement in the agreement
with the diffraction data and were abandoned.
;
#=============================================================

_cell_length_a                   10.8575(2)
_cell_angle_alpha                90
_cell_length_b                   9.3133(2)
_cell_angle_beta                 90.8093(7)
_cell_length_c                   14.1063(3)
_cell_angle_gamma                90
_cell_volume                     1426.27(5)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2

# choose from: rm (reference molecule of
# known chirality), ad (anomolous
# dispersion - ie. Flack param), rmad
# (both rm and ad), syn (known from
# synthetic pathway), unk (unknown)
# or . (not applicable).

_chemical_absolute_configuration .

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 International_Tables_Vol_IV_Table_2.2B
'Li ' -0.0003 0.0001 1.1282 3.9546 0.7508 1.0524 0.6175 85.3905 0.4653 168.2610
0.0377 International_Tables_Vol_IV_Table_2.2B
'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 International_Tables_Vol_IV_Table_2.2B


_cell_formula_units_Z            2
_chemical_formula_sum            ' C26 H50 Li2 N4 '
_chemical_formula_moiety         ' C26 H50 Li2 N4 '
_chemical_compound_source        
;
synthesis as described
;
_chemical_formula_weight         432.58


_cell_measurement_reflns_used    14757
_cell_measurement_theta_min      5
_cell_measurement_theta_max      28
_cell_measurement_temperature    150

_exptl_crystal_description       ' prism '
_exptl_crystal_colour            ' orange '
_exptl_crystal_size_min          0.18
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_max          0.40

_exptl_crystal_density_diffrn    1.007
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.058


_diffrn_measurement_method       \w

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.99

_diffrn_standards_interval_time  0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0.00

_diffrn_ambient_temperature      150
_diffrn_reflns_number            14757
_reflns_number_total             3232
#3432 unique reflections including absences
_diffrn_reflns_av_R_equivalents  0.033

_diffrn_reflns_theta_min         5.186
_diffrn_reflns_theta_max         27.475
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        27.475
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -14
_reflns_limit_h_max              14
_reflns_limit_k_min              0
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              18



_refine_diff_density_min         -0.35
_refine_diff_density_max         0.63


_refine_ls_number_reflns         2297
_refine_ls_number_restraints     27
_refine_ls_number_parameters     181

#_refine_ls_R_factor_ref 0.0709
_refine_ls_wR_factor_ref         0.0961
_refine_ls_goodness_of_fit_ref   1.0173

#_reflns_number_all 3232
_refine_ls_R_factor_all          0.0934
_refine_ls_wR_factor_all         0.1117

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>3.00u(I)
_reflns_number_gt                2297
_refine_ls_R_factor_gt           0.0709
_refine_ls_wR_factor_gt          0.0961


_refine_ls_shift/su_max          0.017615
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
1.85 1.58 1.10
;
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073

# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

# Replace trailing . with the number of unfound
# hydrogen atoms attaced to relavent atom

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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
Li1 Li 0.6378(3) 0.3415(3) 0.4736(2) 0.0319 1.0000 Uani .
C1 C 0.55369(18) 0.4159(2) 0.60785(12) 0.0332 1.0000 Uani D
C2 C 0.66283(17) 0.4958(2) 0.59147(14) 0.0359 1.0000 Uani D
C3 C 0.65313(16) 0.57397(19) 0.50548(14) 0.0324 1.0000 Uani D
C4 C 0.53071(15) 0.54889(17) 0.46832(12) 0.0265 1.0000 Uani .
C5 C 0.5270(3) 0.3246(3) 0.69310(16) 0.0521 1.0000 Uani D
C6 C 0.7717(2) 0.5054(3) 0.65888(19) 0.0587 1.0000 Uani D
C7 C 0.7487(2) 0.6734(3) 0.4665(2) 0.0519 1.0000 Uani D
N1 N 0.79323(15) 0.19223(19) 0.48149(13) 0.0422 1.0000 Uani .
C8 C 0.7645(2) 0.0775(3) 0.4135(2) 0.0613 1.0000 Uani .
C9 C 0.6999(2) 0.1280(3) 0.32726(19) 0.0574 1.0000 Uani .
N2 N 0.59175(15) 0.21698(18) 0.34904(12) 0.0388 1.0000 Uani .
C10 C 0.9004(2) 0.2734(4) 0.4538(3) 0.0698 1.0000 Uani .
C11 C 0.8119(3) 0.1264(3) 0.5745(2) 0.0662 1.0000 Uani .
C12 C 0.4838(3) 0.1358(3) 0.37551(18) 0.0573 1.0000 Uani .
C13 C 0.5605(3) 0.3002(3) 0.26447(17) 0.0569 1.0000 Uani .
H51 H 0.474(3) 0.378(3) 0.741(2) 0.087(10) 1.0000 Uiso D
H52 H 0.602(3) 0.288(4) 0.722(2) 0.101(12) 1.0000 Uiso D
H53 H 0.481(3) 0.242(3) 0.678(2) 0.076(10) 1.0000 Uiso D
H61 H 0.768(3) 0.592(4) 0.699(3) 0.112(14) 1.0000 Uiso D
H62 H 0.853(3) 0.503(3) 0.6259(19) 0.063(8) 1.0000 Uiso D
H63 H 0.768(3) 0.426(4) 0.705(3) 0.106(14) 1.0000 Uiso D
H71 H 0.761(3) 0.756(4) 0.509(2) 0.087(11) 1.0000 Uiso D
H72 H 0.718(3) 0.716(4) 0.403(2) 0.099(12) 1.0000 Uiso D
H73 H 0.830(3) 0.627(4) 0.459(3) 0.131(16) 1.0000 Uiso D
H81 H 0.8434 0.0311 0.3945 0.0734 1.0000 Uiso .
H82 H 0.7112 0.0051 0.4455 0.0734 1.0000 Uiso .
H91 H 0.7584 0.1862 0.2889 0.0688 1.0000 Uiso .
H92 H 0.6721 0.0427 0.2896 0.0688 1.0000 Uiso .
H101 H 0.9173 0.3504 0.5017 0.0840 1.0000 Uiso .
H102 H 0.9732 0.2078 0.4505 0.0840 1.0000 Uiso .
H103 H 0.8850 0.3179 0.3903 0.0840 1.0000 Uiso .
H111 H 0.8317 0.2026 0.6223 0.0793 1.0000 Uiso .
H112 H 0.8817 0.0565 0.5717 0.0793 1.0000 Uiso .
H113 H 0.7352 0.0750 0.5933 0.0793 1.0000 Uiso .
H121 H 0.4147 0.2034 0.3891 0.0688 1.0000 Uiso .
H122 H 0.5030 0.0776 0.4334 0.0688 1.0000 Uiso .
H123 H 0.4591 0.0705 0.3223 0.0688 1.0000 Uiso .
H131 H 0.4872 0.3618 0.2773 0.0683 1.0000 Uiso .
H132 H 0.6319 0.3624 0.2474 0.0683 1.0000 Uiso .
H133 H 0.5411 0.2334 0.2108 0.0683 1.0000 Uiso .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Li1 0.0315(14) 0.0324(15) 0.0319(14) -0.0032(12) 0.0003(11) 0.0015(12)
C1 0.0385(9) 0.0351(9) 0.0261(8) -0.0004(7) 0.0007(7) 0.0095(7)
C2 0.0310(9) 0.0404(10) 0.0361(9) -0.0104(8) -0.0068(7) 0.0068(7)
C3 0.0267(8) 0.0303(9) 0.0403(9) -0.0056(7) 0.0020(7) -0.0009(6)
C4 0.0254(8) 0.0264(8) 0.0276(7) 0.0000(7) 0.0026(6) 0.0029(6)
C5 0.0671(15) 0.0548(14) 0.0347(10) 0.0146(10) 0.0094(10) 0.0188(12)
C6 0.0458(13) 0.0760(18) 0.0536(13) -0.0276(13) -0.0222(11) 0.0175(12)
C7 0.0384(11) 0.0428(12) 0.0750(16) -0.0066(11) 0.0143(11) -0.0115(9)
N1 0.0366(9) 0.0466(10) 0.0432(9) -0.0096(7) -0.0061(7) 0.0109(7)
C8 0.0602(14) 0.0575(14) 0.0657(15) -0.0243(12) -0.0177(12) 0.0272(12)
C9 0.0529(13) 0.0613(15) 0.0577(13) -0.0218(12) -0.0080(11) 0.0179(11)
N2 0.0362(8) 0.0394(9) 0.0406(9) -0.0112(7) -0.0056(7) 0.0066(6)
C10 0.0441(13) 0.0727(18) 0.093(2) -0.0188(16) 0.0138(13) 0.0012(12)
C11 0.0776(17) 0.0639(16) 0.0567(14) 0.0013(13) -0.0100(13) 0.0248(14)
C12 0.0681(15) 0.0504(13) 0.0536(13) -0.0055(11) 0.0051(11) -0.0133(12)
C13 0.0700(16) 0.0602(15) 0.0405(12) -0.0037(11) 0.0048(10) 0.0049(12)
_refine_ls_extinction_method     None
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Li1 . C1 . 2.224(3) yes
Li1 . C2 . 2.211(3) yes
Li1 . C3 . 2.217(4) yes
Li1 . C4 . 2.255(3) yes
Li1 . C4 2_666 2.258(3) yes
Li1 . N1 . 2.189(3) yes
Li1 . N2 . 2.158(3) yes
C1 . C2 . 1.421(3) yes
C1 . C4 2_666 1.440(2) yes
C1 . C5 . 1.504(3) yes
C2 . C3 . 1.417(3) yes
C2 . C6 . 1.509(3) yes
C3 . C4 . 1.441(2) yes
C3 . C7 . 1.501(3) yes
C4 . C4 2_666 1.446(3) yes
C5 . H51 . 1.02(3) no
C5 . H52 . 0.97(3) no
C5 . H53 . 0.94(3) no
C6 . H61 . 0.99(3) no
C6 . H62 . 1.00(3) no
C6 . H63 . 0.99(3) no
C7 . H71 . 0.98(3) no
C7 . H72 . 1.03(3) no
C7 . H73 . 0.99(4) no
N1 . C8 . 1.466(3) yes
N1 . C10 . 1.446(3) yes
N1 . C11 . 1.460(3) yes
C8 . C9 . 1.473(4) yes
C8 . H81 . 1.000 no
C8 . H82 . 1.000 no
C9 . N2 . 1.474(3) yes
C9 . H91 . 1.000 no
C9 . H92 . 1.000 no
N2 . C12 . 1.448(3) yes
N2 . C13 . 1.459(3) yes
C10 . H101 . 1.000 no
C10 . H102 . 1.000 no
C10 . H103 . 1.000 no
C11 . H111 . 1.000 no
C11 . H112 . 1.000 no
C11 . H113 . 1.000 no
C12 . H121 . 1.000 no
C12 . H122 . 1.000 no
C12 . H123 . 1.000 no
C13 . H131 . 1.000 no
C13 . H132 . 1.000 no
C13 . H133 . 1.000 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 . Li1 . C2 . 37.38(9) yes
C1 . Li1 . C3 . 63.52(11) yes
C2 . Li1 . C3 . 37.34(9) yes
C1 . Li1 . C4 . 62.88(10) yes
C2 . Li1 . C4 . 61.72(10) yes
C3 . Li1 . C4 . 37.59(8) yes
C1 . Li1 . C4 2_666 37.47(8) yes
C2 . Li1 . C4 2_666 61.67(10) yes
C3 . Li1 . C4 2_666 62.89(10) yes
C4 . Li1 . C4 2_666 37.36(9) yes
C1 . Li1 . N1 . 118.69(15) yes
C2 . Li1 . N1 . 106.74(14) yes
C3 . Li1 . N1 . 123.66(15) yes
C4 . Li1 . N1 . 160.51(17) yes
C4 2_666 Li1 . N1 . 153.73(16) yes
C1 . Li1 . N2 . 140.12(16) yes
C2 . Li1 . N2 . 170.39(17) yes
C3 . Li1 . N2 . 134.89(16) yes
C4 . Li1 . N2 . 108.67(14) yes
C4 2_666 Li1 . N2 . 111.03(14) yes
N1 . Li1 . N2 . 82.49(12) yes
Li1 . C1 . C2 . 70.82(13) yes
Li1 . C1 . C4 2_666 72.56(12) yes
C2 . C1 . C4 2_666 106.41(16) yes
Li1 . C1 . C5 . 126.24(16) yes
C2 . C1 . C5 . 126.63(18) yes
C4 2_666 C1 . C5 . 126.68(19) yes
Li1 . C2 . C1 . 71.80(13) yes
Li1 . C2 . C3 . 71.54(13) yes
C1 . C2 . C3 . 110.87(16) yes
Li1 . C2 . C6 . 126.83(16) yes
C1 . C2 . C6 . 125.2(2) yes
C3 . C2 . C6 . 123.8(2) yes
Li1 . C3 . C2 . 71.12(13) yes
Li1 . C3 . C4 . 72.64(12) yes
C2 . C3 . C4 . 106.56(15) yes
Li1 . C3 . C7 . 125.35(16) yes
C2 . C3 . C7 . 125.96(19) yes
C4 . C3 . C7 . 127.27(19) yes
Li1 . C4 . Li1 2_666 142.64(9) yes
Li1 . C4 . C1 2_666 122.84(14) yes
Li1 2_666 C4 . C1 2_666 69.97(12) yes
Li1 . C4 . C3 . 69.78(12) yes
Li1 2_666 C4 . C3 . 122.85(14) yes
C1 2_666 C4 . C3 . 143.94(17) yes
Li1 . C4 . C4 2_666 71.46(14) yes
Li1 2_666 C4 . C4 2_666 71.18(14) yes
C1 2_666 C4 . C4 2_666 108.10(18) yes
C3 . C4 . C4 2_666 107.96(18) yes
C1 . C5 . H51 . 112.0(17) no
C1 . C5 . H52 . 111.6(19) no
H51 . C5 . H52 . 111(2) no
C1 . C5 . H53 . 113.0(18) no
H51 . C5 . H53 . 104(2) no
H52 . C5 . H53 . 105(2) no
C2 . C6 . H61 . 112(2) no
C2 . C6 . H62 . 113.1(16) no
H61 . C6 . H62 . 109(2) no
C2 . C6 . H63 . 109(2) no
H61 . C6 . H63 . 103(2) no
H62 . C6 . H63 . 109(2) no
C3 . C7 . H71 . 110.4(18) no
C3 . C7 . H72 . 109.9(19) no
H71 . C7 . H72 . 105(2) no
C3 . C7 . H73 . 113(2) no
H71 . C7 . H73 . 107(3) no
H72 . C7 . H73 . 110(3) no
Li1 . N1 . C8 . 105.85(15) yes
Li1 . N1 . C10 . 106.12(17) yes
C8 . N1 . C10 . 111.7(2) yes
Li1 . N1 . C11 . 114.19(17) yes
C8 . N1 . C11 . 107.9(2) yes
C10 . N1 . C11 . 111.1(2) yes
N1 . C8 . C9 . 113.7(2) yes
N1 . C8 . H81 . 108.406 no
C9 . C8 . H81 . 108.406 no
N1 . C8 . H82 . 108.405 no
C9 . C8 . H82 . 108.405 no
H81 . C8 . H82 . 109.466 no
C8 . C9 . N2 . 112.3(2) yes
C8 . C9 . H91 . 108.770 no
N2 . C9 . H91 . 108.770 no
C8 . C9 . H92 . 108.772 no
N2 . C9 . H92 . 108.771 no
H91 . C9 . H92 . 109.466 no
Li1 . N2 . C9 . 107.22(15) yes
Li1 . N2 . C12 . 104.44(15) yes
C9 . N2 . C12 . 114.3(2) yes
Li1 . N2 . C13 . 115.40(16) yes
C9 . N2 . C13 . 107.76(19) yes
C12 . N2 . C13 . 107.98(18) yes
N1 . C10 . H101 . 109.466 no
N1 . C10 . H102 . 109.467 no
H101 . C10 . H102 . 109.475 no
N1 . C10 . H103 . 109.467 no
H101 . C10 . H103 . 109.475 no
H102 . C10 . H103 . 109.477 no
N1 . C11 . H111 . 109.467 no
N1 . C11 . H112 . 109.466 no
H111 . C11 . H112 . 109.476 no
N1 . C11 . H113 . 109.467 no
H111 . C11 . H113 . 109.476 no
H112 . C11 . H113 . 109.476 no
N2 . C12 . H121 . 109.467 no
N2 . C12 . H122 . 109.466 no
H121 . C12 . H122 . 109.475 no
N2 . C12 . H123 . 109.467 no
H121 . C12 . H123 . 109.476 no
H122 . C12 . H123 . 109.476 no
N2 . C13 . H131 . 109.467 no
N2 . C13 . H132 . 109.467 no
H131 . C13 . H132 . 109.476 no
N2 . C13 . H133 . 109.467 no
H131 . C13 . H133 . 109.475 no
H132 . C13 . H133 . 109.476 no