# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2009

data_global

_journal_coden_Cambridge         222
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Michael Buchmeiser'
'Bantu Bhasker'
'S. Blechert'
'Gajanan Pawar'
'Jochen Weckesser'
'Klaus Wurst'

_publ_contact_author_name        'Michael Buchmeiser'
_publ_contact_author_email       MICHAEL.BUCHMEISER@IOM-LEIPZIG.DE

_publ_section_title              
;
Ring-Opening Metathesis Polymerization-Derived, Polymer-Bound
Cu-Catalysts for Click-Chemistry and Hydrosilylation Reactions
Under Micellar Conditions
;

# Attachment '1.CIF'

data_1
_database_code_depnum_ccdc_archive 'CCDC 731614'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H28 Cl Cu N2'
_chemical_formula_sum            'C22 H28 Cl Cu N2'
_chemical_formula_weight         419.45

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   30.4627(5)
_cell_length_b                   8.9030(2)
_cell_length_c                   15.8730(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4304.91(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    233(2)
_cell_measurement_reflns_used    25513
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      26.0

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1760
_exptl_absorpt_coefficient_mu    1.146
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      233(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  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- and omega-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18276
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.34
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3761
_reflns_number_gt                3253
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       ?
_computing_data_reduction        'DENZO and SCALEPACK'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0453P)^2^+5.5529P] 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         3761
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1146
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.125659(12) 0.20068(4) 0.25404(2) 0.04045(15) Uani 1 1 d . . .
Cl1 Cl 0.12340(3) 0.33937(13) 0.14703(6) 0.0686(3) Uani 1 1 d . . .
N1 N 0.10345(8) 0.1304(3) 0.42021(14) 0.0380(6) Uani 1 1 d . . .
N2 N 0.15444(7) -0.0318(3) 0.36577(13) 0.0346(5) Uani 1 1 d . . .
C1 C 0.12804(8) 0.0874(3) 0.35483(17) 0.0333(6) Uani 1 1 d . . .
C2 C 0.10583(12) 0.0647(4) 0.50564(19) 0.0526(8) Uani 1 1 d . . .
H2A H 0.0826 -0.0104 0.5126 0.063 Uiso 1 1 calc . . .
H2B H 0.1014 0.1435 0.5479 0.063 Uiso 1 1 calc . . .
C3 C 0.15018(13) -0.0081(4) 0.5184(2) 0.0558(9) Uani 1 1 d . . .
H3A H 0.1731 0.0691 0.5208 0.067 Uiso 1 1 calc . . .
H3B H 0.1505 -0.0637 0.5716 0.067 Uiso 1 1 calc . . .
C4 C 0.15888(11) -0.1136(3) 0.44591(18) 0.0435(7) Uani 1 1 d . . .
H4A H 0.1886 -0.1551 0.4507 0.052 Uiso 1 1 calc . . .
H4B H 0.1379 -0.1971 0.4475 0.052 Uiso 1 1 calc . . .
C5 C 0.07386(10) 0.2565(4) 0.40872(17) 0.0409(7) Uani 1 1 d . . .
C6 C 0.03088(11) 0.2272(4) 0.3842(2) 0.0542(9) Uani 1 1 d . . .
C7 C 0.00303(11) 0.3505(6) 0.3747(3) 0.0682(11) Uani 1 1 d . . .
H7 H -0.0261 0.3340 0.3572 0.082 Uiso 1 1 calc . . .
C8 C 0.01668(12) 0.4953(5) 0.3900(2) 0.0630(10) Uani 1 1 d . . .
C9 C 0.05921(12) 0.5180(4) 0.4158(2) 0.0561(9) Uani 1 1 d . . .
H9 H 0.0685 0.6164 0.4277 0.067 Uiso 1 1 calc . . .
C10 C 0.08895(10) 0.4010(4) 0.42478(19) 0.0453(7) Uani 1 1 d . . .
C11 C 0.17975(9) -0.0869(3) 0.29540(16) 0.0336(6) Uani 1 1 d . . .
C12 C 0.16041(10) -0.1888(3) 0.24007(18) 0.0389(7) Uani 1 1 d . . .
C13 C 0.18602(11) -0.2438(4) 0.17449(18) 0.0439(7) Uani 1 1 d . . .
H13 H 0.1736 -0.3127 0.1364 0.053 Uiso 1 1 calc . . .
C14 C 0.22914(11) -0.2005(4) 0.16362(19) 0.0454(8) Uani 1 1 d . . .
C15 C 0.24736(10) -0.1005(4) 0.2202(2) 0.0459(7) Uani 1 1 d . . .
H15 H 0.2767 -0.0706 0.2133 0.055 Uiso 1 1 calc . . .
C16 C 0.22328(9) -0.0430(3) 0.28730(18) 0.0377(6) Uani 1 1 d . . .
C61 C 0.01483(14) 0.0688(5) 0.3683(3) 0.0833(13) Uani 1 1 d . . .
H61A H -0.0156 0.0716 0.3506 0.125 Uiso 1 1 calc R . .
H61B H 0.0174 0.0104 0.4197 0.125 Uiso 1 1 calc R . .
H61C H 0.0325 0.0229 0.3245 0.125 Uiso 1 1 calc R . .
C81 C -0.01484(15) 0.6254(6) 0.3793(3) 0.0950(17) Uani 1 1 d . . .
H81A H -0.0358 0.6256 0.4254 0.143 Uiso 1 1 calc R . .
H81B H -0.0304 0.6149 0.3263 0.143 Uiso 1 1 calc R . .
H81C H 0.0014 0.7190 0.3794 0.143 Uiso 1 1 calc R . .
C101 C 0.13589(11) 0.4304(4) 0.4494(3) 0.0607(9) Uani 1 1 d . . .
H10A H 0.1373 0.5197 0.4843 0.091 Uiso 1 1 calc R . .
H10B H 0.1534 0.4453 0.3990 0.091 Uiso 1 1 calc R . .
H10C H 0.1472 0.3452 0.4807 0.091 Uiso 1 1 calc R . .
C121 C 0.11335(12) -0.2375(5) 0.2487(2) 0.0586(9) Uani 1 1 d . . .
H12A H 0.0942 -0.1574 0.2296 0.088 Uiso 1 1 calc R . .
H12B H 0.1071 -0.2598 0.3073 0.088 Uiso 1 1 calc R . .
H12C H 0.1084 -0.3265 0.2148 0.088 Uiso 1 1 calc R . .
C141 C 0.25609(14) -0.2618(5) 0.0909(2) 0.0654(10) Uani 1 1 d . . .
H14A H 0.2865 -0.2714 0.1082 0.098 Uiso 1 1 calc R . .
H14B H 0.2542 -0.1936 0.0434 0.098 Uiso 1 1 calc R . .
H14C H 0.2448 -0.3595 0.0747 0.098 Uiso 1 1 calc R . .
C161 C 0.24437(11) 0.0631(4) 0.3494(2) 0.0536(8) Uani 1 1 d . . .
H16A H 0.2487 0.0119 0.4027 0.080 Uiso 1 1 calc R . .
H16B H 0.2255 0.1495 0.3578 0.080 Uiso 1 1 calc R . .
H16C H 0.2725 0.0960 0.3277 0.080 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
Cu1 0.0432(2) 0.0471(3) 0.0311(2) 0.00519(16) 0.00087(14) 0.01248(16)
Cl1 0.0805(6) 0.0771(7) 0.0482(5) 0.0253(5) 0.0065(4) 0.0258(5)
N1 0.0428(13) 0.0403(14) 0.0310(12) 0.0007(11) 0.0049(10) 0.0088(11)
N2 0.0413(12) 0.0345(13) 0.0280(11) 0.0007(10) 0.0014(9) 0.0061(10)
C1 0.0330(14) 0.0367(16) 0.0303(14) -0.0030(12) -0.0005(11) 0.0021(12)
C2 0.068(2) 0.055(2) 0.0345(16) 0.0062(15) 0.0131(15) 0.0150(18)
C3 0.079(2) 0.053(2) 0.0348(16) 0.0093(15) -0.0005(16) 0.0153(19)
C4 0.0571(18) 0.0379(17) 0.0354(15) 0.0091(13) 0.0018(13) 0.0089(14)
C5 0.0412(16) 0.0504(18) 0.0312(14) -0.0002(14) 0.0066(12) 0.0132(14)
C6 0.0459(18) 0.069(2) 0.0473(18) -0.0074(17) 0.0023(15) 0.0093(17)
C7 0.0405(19) 0.106(3) 0.058(2) 0.000(2) 0.0002(15) 0.022(2)
C8 0.060(2) 0.074(3) 0.055(2) 0.012(2) 0.0132(18) 0.034(2)
C9 0.063(2) 0.049(2) 0.056(2) 0.0107(17) 0.0168(17) 0.0190(17)
C10 0.0466(17) 0.0496(19) 0.0395(16) 0.0032(14) 0.0082(13) 0.0122(15)
C11 0.0387(14) 0.0320(15) 0.0302(14) 0.0027(12) 0.0008(11) 0.0073(12)
C12 0.0390(15) 0.0426(17) 0.0352(15) -0.0008(13) -0.0012(12) 0.0024(13)
C13 0.0549(19) 0.0428(17) 0.0341(15) -0.0050(14) -0.0032(13) 0.0072(15)
C14 0.0517(19) 0.0474(19) 0.0372(16) 0.0059(14) 0.0076(14) 0.0171(15)
C15 0.0397(16) 0.0488(18) 0.0491(17) 0.0074(16) 0.0080(14) 0.0063(14)
C16 0.0418(15) 0.0317(15) 0.0397(15) 0.0053(13) -0.0010(12) 0.0021(12)
C61 0.057(2) 0.095(3) 0.098(3) -0.023(3) -0.010(2) -0.009(2)
C81 0.082(3) 0.113(4) 0.090(3) 0.033(3) 0.018(3) 0.060(3)
C101 0.058(2) 0.052(2) 0.072(2) -0.0058(19) -0.0039(18) 0.0064(17)
C121 0.0451(18) 0.078(3) 0.052(2) -0.0146(19) -0.0013(14) -0.0140(19)
C141 0.073(2) 0.072(2) 0.051(2) -0.0042(19) 0.0204(18) 0.022(2)
C161 0.0517(19) 0.051(2) 0.058(2) -0.0034(17) 0.0002(16) -0.0127(16)

_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
Cu1 C1 1.892(3) . ?
Cu1 Cl1 2.1011(9) . ?
N1 C1 1.336(3) . ?
N1 C5 1.451(4) . ?
N1 C2 1.479(4) . ?
N2 C1 1.343(4) . ?
N2 C11 1.443(3) . ?
N2 C4 1.472(3) . ?
C2 C3 1.512(5) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 C4 1.509(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 C10 1.390(5) . ?
C5 C6 1.391(5) . ?
C6 C7 1.395(5) . ?
C6 C61 1.514(6) . ?
C7 C8 1.376(6) . ?
C7 H7 0.9400 . ?
C8 C9 1.373(5) . ?
C8 C81 1.514(5) . ?
C9 C10 1.388(4) . ?
C9 H9 0.9400 . ?
C10 C101 1.505(5) . ?
C11 C16 1.388(4) . ?
C11 C12 1.393(4) . ?
C12 C13 1.390(4) . ?
C12 C121 1.504(5) . ?
C13 C14 1.380(5) . ?
C13 H13 0.9400 . ?
C14 C15 1.381(5) . ?
C14 C141 1.518(4) . ?
C15 C16 1.390(4) . ?
C15 H15 0.9400 . ?
C16 C161 1.509(4) . ?
C61 H61A 0.9700 . ?
C61 H61B 0.9700 . ?
C61 H61C 0.9700 . ?
C81 H81A 0.9700 . ?
C81 H81B 0.9700 . ?
C81 H81C 0.9700 . ?
C101 H10A 0.9700 . ?
C101 H10B 0.9700 . ?
C101 H10C 0.9700 . ?
C121 H12A 0.9700 . ?
C121 H12B 0.9700 . ?
C121 H12C 0.9700 . ?
C141 H14A 0.9700 . ?
C141 H14B 0.9700 . ?
C141 H14C 0.9700 . ?
C161 H16A 0.9700 . ?
C161 H16B 0.9700 . ?
C161 H16C 0.9700 . ?

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
C1 Cu1 Cl1 176.20(9) . . ?
C1 N1 C5 118.2(2) . . ?
C1 N1 C2 124.8(2) . . ?
C5 N1 C2 116.9(2) . . ?
C1 N2 C11 119.2(2) . . ?
C1 N2 C4 123.9(2) . . ?
C11 N2 C4 116.9(2) . . ?
N1 C1 N2 117.5(2) . . ?
N1 C1 Cu1 118.8(2) . . ?
N2 C1 Cu1 123.61(19) . . ?
N1 C2 C3 109.6(2) . . ?
N1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
N1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C4 C3 C2 108.8(3) . . ?
C4 C3 H3A 109.9 . . ?
C2 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
N2 C4 C3 109.6(2) . . ?
N2 C4 H4A 109.8 . . ?
C3 C4 H4A 109.8 . . ?
N2 C4 H4B 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
C10 C5 C6 122.4(3) . . ?
C10 C5 N1 119.2(3) . . ?
C6 C5 N1 118.3(3) . . ?
C5 C6 C7 117.1(4) . . ?
C5 C6 C61 121.7(3) . . ?
C7 C6 C61 121.2(3) . . ?
C8 C7 C6 122.3(3) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C9 C8 C7 118.4(3) . . ?
C9 C8 C81 121.2(4) . . ?
C7 C8 C81 120.3(4) . . ?
C8 C9 C10 122.4(4) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
C9 C10 C5 117.4(3) . . ?
C9 C10 C101 121.1(3) . . ?
C5 C10 C101 121.5(3) . . ?
C16 C11 C12 121.9(3) . . ?
C16 C11 N2 119.1(2) . . ?
C12 C11 N2 118.9(2) . . ?
C13 C12 C11 117.7(3) . . ?
C13 C12 C121 120.1(3) . . ?
C11 C12 C121 122.2(3) . . ?
C14 C13 C12 121.9(3) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C13 C14 C15 118.8(3) . . ?
C13 C14 C141 120.6(3) . . ?
C15 C14 C141 120.6(3) . . ?
C14 C15 C16 121.5(3) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C11 C16 C15 118.1(3) . . ?
C11 C16 C161 121.5(3) . . ?
C15 C16 C161 120.4(3) . . ?
C6 C61 H61A 109.5 . . ?
C6 C61 H61B 109.5 . . ?
H61A C61 H61B 109.5 . . ?
C6 C61 H61C 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
C8 C81 H81A 109.5 . . ?
C8 C81 H81B 109.5 . . ?
H81A C81 H81B 109.5 . . ?
C8 C81 H81C 109.5 . . ?
H81A C81 H81C 109.5 . . ?
H81B C81 H81C 109.5 . . ?
C10 C101 H10A 109.5 . . ?
C10 C101 H10B 109.5 . . ?
H10A C101 H10B 109.5 . . ?
C10 C101 H10C 109.5 . . ?
H10A C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
C12 C121 H12A 109.5 . . ?
C12 C121 H12B 109.5 . . ?
H12A C121 H12B 109.5 . . ?
C12 C121 H12C 109.5 . . ?
H12A C121 H12C 109.5 . . ?
H12B C121 H12C 109.5 . . ?
C14 C141 H14A 109.5 . . ?
C14 C141 H14B 109.5 . . ?
H14A C141 H14B 109.5 . . ?
C14 C141 H14C 109.5 . . ?
H14A C141 H14C 109.5 . . ?
H14B C141 H14C 109.5 . . ?
C16 C161 H16A 109.5 . . ?
C16 C161 H16B 109.5 . . ?
H16A C161 H16B 109.5 . . ?
C16 C161 H16C 109.5 . . ?
H16A C161 H16C 109.5 . . ?
H16B C161 H16C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.052