# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2011


data_global

_journal_coden_Cambridge         222
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Lang, Thomas'
'Graf, Ernest'
'Kyritsakas, Nathalie'
'Hosseini, Mir Wais'

_publ_contact_author_name        'Dr Hosseini, Mir Wais'
_publ_contact_author_email       hosseini@chimie.u-strasbg.fr

_publ_section_title              
;
Open and closed states of a porphyrin based molecular turnstile
;

# Attachment '- Hosseini News.cif'

data_e1377c
_database_code_depnum_ccdc_archive 'CCDC 810526'
#TrackingRef '- Hosseini News.cif'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C44 H24 Cl2 N8 Sn'

_chemical_formula_sum            'C44 H24 Cl2 N8 Sn'

_chemical_formula_weight         854.30

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic

_symmetry_space_group_name_H-M   Pnna

_symmetry_space_group_name_Hall  '-P 2a 2bc'

loop_

_symmetry_equiv_pos_as_xyz

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

_cell_length_a                   28.3515(17)

_cell_length_b                   14.9001(9)

_cell_length_c                   12.9781(8)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.00

_cell_angle_gamma                90.00

_cell_volume                     5482.5(6)

_cell_formula_units_Z            4

_cell_measurement_temperature    173(2)

_cell_measurement_reflns_used    4827

_cell_measurement_theta_min      2.53

_cell_measurement_theta_max      22.43

_exptl_crystal_description       prism

_exptl_crystal_colour            purple

_exptl_crystal_size_max          0.10

_exptl_crystal_size_mid          0.08

_exptl_crystal_size_min          0.06

_exptl_crystal_density_meas      none

_exptl_crystal_density_diffrn    1.035

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             1712

_exptl_absorpt_coefficient_mu    0.594

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9430

_exptl_absorpt_correction_T_max  0.9652

_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;

Owing to large disorder of the solvent present in the cavities

of this structure, the SQUEEZE command has been applied

;

_diffrn_ambient_temperature      173(2)

_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  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            60675

_diffrn_reflns_av_R_equivalents  0.0514

_diffrn_reflns_av_sigmaI/netI    0.0617

_diffrn_reflns_limit_h_min       0

_diffrn_reflns_limit_h_max       36

_diffrn_reflns_limit_k_min       0

_diffrn_reflns_limit_k_max       19

_diffrn_reflns_limit_l_min       0

_diffrn_reflns_limit_l_max       16

_diffrn_reflns_theta_min         1.44

_diffrn_reflns_theta_max         27.71

_reflns_number_total             6384

_reflns_number_gt                2513

_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;

Refinement of F^2^ against ALL reflections. The weighted R-factor wR and

goodness of fit S are based on F^2^, conventional R-factors R are based

on F, with F set to zero for negative F^2^. The threshold expression of

F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is

not relevant to the choice of reflections for refinement. R-factors based

on F^2^ 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/[\s^2^(Fo^2^)+(0.0846P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         6384

_refine_ls_number_parameters     250

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.1372

_refine_ls_R_factor_gt           0.0775

_refine_ls_wR_factor_ref         0.2069

_refine_ls_wR_factor_gt          0.1938

_refine_ls_goodness_of_fit_ref   1.033

_refine_ls_restrained_S_all      1.033

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000

loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group

Sn1 Sn 1.0000 1.0000 1.0000 0.0746(3) Uani 1 2 d S . .
Cl1 Cl 0.95409(8) 0.99520(11) 1.1575(2) 0.1343(8) Uani 1 1 d . . .
N1 N 0.94727(14) 0.9261(2) 0.9260(4) 0.0714(13) Uani 1 1 d . . .
N2 N 0.96622(15) 1.1189(2) 0.9559(4) 0.0798(14) Uani 1 1 d . . .
C1 C 0.94474(18) 0.8336(3) 0.9224(5) 0.0697(16) Uani 1 1 d . . .
C2 C 0.90116(19) 0.8120(3) 0.8701(5) 0.0793(18) Uani 1 1 d . . .
H2 H 0.8894 0.7533 0.8573 0.095 Uiso 1 1 calc R . .
C3 C 0.88031(19) 0.8887(3) 0.8429(5) 0.0790(18) Uani 1 1 d . . .
H3 H 0.8513 0.8936 0.8065 0.095 Uiso 1 1 calc R . .
C4 C 0.90801(18) 0.9609(3) 0.8764(5) 0.0707(16) Uani 1 1 d . . .
C5 C 0.89704(18) 1.0545(3) 0.8677(5) 0.0727(16) Uani 1 1 d . . .
C6 C 0.92484(19) 1.1252(3) 0.9064(5) 0.0744(17) Uani 1 1 d . . .
C7 C 0.91491(19) 1.2195(3) 0.8902(5) 0.0876(19) Uani 1 1 d . . .
H7 H 0.8890 1.2433 0.8529 0.105 Uiso 1 1 calc R . .
C8 C 0.94925(19) 1.2680(3) 0.9378(5) 0.093(2) Uani 1 1 d . . .
H8 H 0.9510 1.3315 0.9423 0.112 Uiso 1 1 calc R . .
C9 C 0.9826(2) 1.2046(3) 0.9802(5) 0.0736(18) Uani 1 1 d . . .
C10 C 0.97599(18) 0.7742(3) 0.9678(5) 0.0693(17) Uani 1 1 d . . .
C11 C 0.85265(17) 1.0765(3) 0.8092(5) 0.0586(14) Uani 1 1 d . . .
C12 C 0.8130(2) 1.1003(5) 0.8668(6) 0.112(2) Uani 1 1 d . . .
H12 H 0.8141 1.0994 0.9399 0.135 Uiso 1 1 calc R . .
C13 C 0.7715(2) 1.1255(4) 0.8155(6) 0.091(2) Uani 1 1 d . . .
H13 H 0.7452 1.1457 0.8544 0.109 Uiso 1 1 calc R . .
C14 C 0.76855(19) 1.1217(3) 0.7140(5) 0.0665(15) Uani 1 1 d . . .
C15 C 0.8074(2) 1.0964(4) 0.6580(6) 0.092(2) Uani 1 1 d . . .
H15 H 0.8056 1.0935 0.5850 0.111 Uiso 1 1 calc R . .
C16 C 0.8491(2) 1.0752(3) 0.7070(5) 0.0743(16) Uani 1 1 d . . .
H16 H 0.8759 1.0593 0.6669 0.089 Uiso 1 1 calc R . .
C17 C 0.7245(2) 1.1462(4) 0.6648(5) 0.0877(19) Uani 1 1 d . . .
N3 N 0.6905(2) 1.1639(4) 0.6257(5) 0.129(2) Uani 1 1 d . . .
C18 C 0.96537(19) 0.6770(3) 0.9549(5) 0.0755(17) Uani 1 1 d . . .
C19 C 0.9773(2) 0.6287(3) 0.8748(6) 0.097(2) Uani 1 1 d . . .
H19 H 0.9938 0.6562 0.8195 0.116 Uiso 1 1 calc R . .
C20 C 0.9660(3) 0.5355(4) 0.8690(7) 0.112(3) Uani 1 1 d . . .
H20 H 0.9762 0.5025 0.8105 0.134 Uiso 1 1 calc R . .
N4 N 0.9427(2) 0.4942(3) 0.9391(7) 0.111(2) Uani 1 1 d . . .
C21 C 0.9314(3) 0.5405(4) 1.0191(9) 0.150(4) Uani 1 1 d . . .
H21 H 0.9154 0.5108 1.0737 0.181 Uiso 1 1 calc R . .
C22 C 0.9414(3) 0.6327(4) 1.0303(7) 0.129(3) Uani 1 1 d . . .
H22 H 0.9315 0.6638 1.0903 0.154 Uiso 1 1 calc R . .

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 0.0478(3) 0.0229(2) 0.1532(6) -0.0033(3) -0.0150(3) -0.0019(2)
Cl1 0.1113(16) 0.0884(13) 0.203(2) -0.0045(13) -0.0162(16) -0.0081(10)
N1 0.048(3) 0.0275(19) 0.139(4) -0.005(2) -0.015(3) -0.0013(18)
N2 0.051(3) 0.0215(18) 0.167(4) 0.008(2) -0.018(3) -0.0010(18)
C1 0.057(4) 0.036(2) 0.116(5) -0.004(3) -0.002(3) -0.003(2)
C2 0.061(4) 0.032(2) 0.145(6) -0.014(3) -0.017(4) 0.006(2)
C3 0.057(3) 0.038(3) 0.142(5) -0.026(3) -0.025(3) 0.000(2)
C4 0.057(3) 0.028(2) 0.127(5) 0.010(3) -0.010(3) 0.002(2)
C5 0.050(3) 0.033(2) 0.135(5) -0.006(3) 0.001(3) -0.003(2)
C6 0.051(3) 0.027(2) 0.146(5) 0.000(3) -0.018(3) 0.002(2)
C7 0.056(3) 0.035(3) 0.171(6) -0.007(3) -0.019(4) 0.007(2)
C8 0.061(4) 0.023(2) 0.196(7) 0.002(3) -0.028(4) 0.002(2)
C9 0.055(3) 0.029(2) 0.136(6) -0.006(3) -0.005(3) 0.005(2)
C10 0.040(3) 0.030(2) 0.138(5) 0.002(3) -0.013(3) 0.000(2)
C11 0.040(3) 0.023(2) 0.113(5) 0.000(3) -0.003(3) -0.0002(19)
C12 0.068(5) 0.120(6) 0.148(7) 0.019(5) -0.001(5) 0.009(4)
C13 0.045(4) 0.104(5) 0.123(6) 0.015(5) 0.002(4) 0.017(3)
C14 0.049(3) 0.048(3) 0.102(5) 0.014(3) -0.001(4) 0.002(2)
C15 0.055(4) 0.080(4) 0.142(6) 0.001(4) 0.002(4) 0.010(3)
C16 0.057(4) 0.061(3) 0.105(5) -0.005(3) -0.003(4) 0.016(3)
C17 0.068(4) 0.074(4) 0.121(6) 0.032(4) 0.000(4) 0.012(3)
N3 0.061(4) 0.122(5) 0.204(7) 0.058(4) -0.012(4) 0.030(3)
C18 0.054(3) 0.027(2) 0.146(5) -0.012(3) -0.012(4) 0.001(2)
C19 0.099(5) 0.031(3) 0.161(7) -0.001(3) -0.024(5) -0.002(3)
C20 0.114(6) 0.037(3) 0.185(8) -0.022(4) -0.044(6) 0.008(4)
N4 0.087(4) 0.024(3) 0.223(7) 0.004(3) -0.043(5) -0.014(2)
C21 0.120(7) 0.036(4) 0.295(12) -0.014(5) 0.028(7) -0.028(4)
C22 0.108(6) 0.039(3) 0.239(9) -0.021(4) 0.052(6) -0.025(3)

_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 2.090(4) 5_777 ?
Sn1 N1 2.090(4) . ?
Sn1 N2 2.094(4) 5_777 ?
Sn1 N2 2.094(4) . ?
Sn1 Cl1 2.425(3) 5_777 ?
Sn1 Cl1 2.425(3) . ?
N1 C1 1.381(5) . ?
N1 C4 1.386(6) . ?
N2 C6 1.341(6) . ?
N2 C9 1.395(6) . ?
C1 C10 1.384(7) . ?
C1 C2 1.446(7) . ?
C2 C3 1.335(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.401(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.433(6) . ?
C5 C6 1.409(6) . ?
C5 C11 1.506(7) . ?
C6 C7 1.448(6) . ?
C7 C8 1.360(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.446(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(8) 5_777 ?
C10 C9 1.390(8) 5_777 ?
C10 C18 1.489(6) . ?
C11 C16 1.330(7) . ?
C11 C12 1.395(8) . ?
C12 C13 1.403(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.322(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.373(8) . ?
C14 C17 1.449(8) . ?
C15 C16 1.380(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 N3 1.122(7) . ?
C18 C19 1.308(8) . ?
C18 C22 1.362(8) . ?
C19 C20 1.428(7) . ?
C19 H19 0.9500 . ?
C20 N4 1.282(10) . ?
C20 H20 0.9500 . ?
N4 C21 1.286(11) . ?
C21 C22 1.411(8) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

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 N1 179.999(1) 5_777 . ?
N1 Sn1 N2 89.60(15) 5_777 5_777 ?
N1 Sn1 N2 90.40(15) . 5_777 ?
N1 Sn1 N2 90.40(15) 5_777 . ?
N1 Sn1 N2 89.60(15) . . ?
N2 Sn1 N2 180.0(2) 5_777 . ?
N1 Sn1 Cl1 89.30(14) 5_777 5_777 ?
N1 Sn1 Cl1 90.70(14) . 5_777 ?
N2 Sn1 Cl1 90.57(15) 5_777 5_777 ?
N2 Sn1 Cl1 89.43(15) . 5_777 ?
N1 Sn1 Cl1 90.70(14) 5_777 . ?
N1 Sn1 Cl1 89.30(14) . . ?
N2 Sn1 Cl1 89.43(15) 5_777 . ?
N2 Sn1 Cl1 90.57(15) . . ?
Cl1 Sn1 Cl1 179.999(1) 5_777 . ?
C1 N1 C4 108.4(4) . . ?
C1 N1 Sn1 125.3(4) . . ?
C4 N1 Sn1 126.2(3) . . ?
C6 N2 C9 109.6(4) . . ?
C6 N2 Sn1 126.2(3) . . ?
C9 N2 Sn1 124.1(4) . . ?
N1 C1 C10 126.2(5) . . ?
N1 C1 C2 106.4(4) . . ?
C10 C1 C2 127.2(4) . . ?
C3 C2 C1 108.2(4) . . ?
C3 C2 H2 125.9 . . ?
C1 C2 H2 125.9 . . ?
C2 C3 C4 109.1(5) . . ?
C2 C3 H3 125.5 . . ?
C4 C3 H3 125.5 . . ?
N1 C4 C3 107.9(4) . . ?
N1 C4 C5 125.1(4) . . ?
C3 C4 C5 126.9(5) . . ?
C6 C5 C4 125.3(5) . . ?
C6 C5 C11 119.0(4) . . ?
C4 C5 C11 115.7(4) . . ?
N2 C6 C5 127.4(4) . . ?
N2 C6 C7 107.9(4) . . ?
C5 C6 C7 124.4(5) . . ?
C8 C7 C6 108.0(5) . . ?
C8 C7 H7 126.0 . . ?
C6 C7 H7 126.0 . . ?
C7 C8 C9 107.1(4) . . ?
C7 C8 H8 126.4 . . ?
C9 C8 H8 126.4 . . ?
C10 C9 N2 126.8(4) 5_777 . ?
C10 C9 C8 126.1(4) 5_777 . ?
N2 C9 C8 107.1(5) . . ?
C1 C10 C9 127.0(4) . 5_777 ?
C1 C10 C18 116.4(5) . . ?
C9 C10 C18 116.5(4) 5_777 . ?
C16 C11 C12 118.5(6) . . ?
C16 C11 C5 124.2(5) . . ?
C12 C11 C5 117.3(6) . . ?
C11 C12 C13 119.4(7) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 120.9(7) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 119.2(6) . . ?
C13 C14 C17 118.9(6) . . ?
C15 C14 C17 121.9(6) . . ?
C14 C15 C16 120.5(7) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 121.4(6) . . ?
C11 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
N3 C17 C14 178.8(8) . . ?
C19 C18 C22 115.7(5) . . ?
C19 C18 C10 124.9(6) . . ?
C22 C18 C10 119.4(6) . . ?
C18 C19 C20 121.2(7) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
N4 C20 C19 123.0(7) . . ?
N4 C20 H20 118.5 . . ?
C19 C20 H20 118.5 . . ?
C20 N4 C21 116.3(6) . . ?
N4 C21 C22 123.7(8) . . ?
N4 C21 H21 118.1 . . ?
C22 C21 H21 118.1 . . ?
C18 C22 C21 119.9(7) . . ?
C18 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.992

_diffrn_reflns_theta_full        27.71

_diffrn_measured_fraction_theta_full 0.992

_refine_diff_density_max         1.499

_refine_diff_density_min         -0.594

_refine_diff_density_rms         0.171

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.250 0.721 -0.250 1166.4 336.1
2 0.750 0.718 0.250 1166.3 335.2
_platon_squeeze_details          
;
;