# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Catherine Cazin'
_publ_contact_author_email       cc111@st-andrews.ac.uk

_publ_section_title              
;
Simple and Versatile Synthesis
of Copper and Silver N-Heterocyclic Carbene Complexes
in Water or Organic Solvents
;
loop_
_publ_author_name
'Cecilia Citadelle'
'E.Le Nouy'
'Fabrice Bisaro'
'Alexandra Slawin'
'Catherine Cazin'

# Attachment '- SICy=O.CIF'

data_SICyO
_database_code_depnum_ccdc_archive 'CCDC 761660'
#TrackingRef '- SICy=O.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H26 N2 O'
_chemical_formula_sum            'C15 H26 N2 O'
_chemical_formula_weight         250.38

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   21.439(13)
_cell_length_b                   5.948(3)
_cell_length_c                   11.280(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.636(15)
_cell_angle_gamma                90.00
_cell_volume                     1436.8(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    366(2)
_cell_measurement_reflns_used    2629
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      28.6

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9565
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      366(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8917
_diffrn_reflns_av_R_equivalents  0.1118
_diffrn_reflns_av_sigmaI/netI    0.1495
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         25.34
_reflns_number_total             2618
_reflns_number_gt                1248
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Corp., 2004)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2004)'
_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^)+(0.0901P)^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     SHELXL
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2618
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1690
_refine_ls_R_factor_gt           0.0797
_refine_ls_wR_factor_ref         0.2110
_refine_ls_wR_factor_gt          0.1693
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_restrained_S_all      0.942
_refine_ls_shift/su_max          0.095
_refine_ls_shift/su_mean         0.010

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
N1 N 0.22339(12) 0.1989(4) 0.2917(3) 0.0360(8) Uani 1 1 d . . .
C2 C 0.25265(15) 0.1666(5) 0.4003(4) 0.0358(9) Uani 1 1 d . . .
O2 O 0.24950(11) -0.0061(3) 0.4619(2) 0.0421(7) Uani 1 1 d . . .
N3 N 0.28669(13) 0.3549(4) 0.4316(3) 0.0355(8) Uani 1 1 d . . .
C4 C 0.28628(16) 0.5084(5) 0.3307(3) 0.0386(10) Uani 1 1 d . . .
H4A H 0.3229 0.4877 0.2845 0.046 Uiso 1 1 calc R . .
H4B H 0.2842 0.6639 0.3563 0.046 Uiso 1 1 calc R . .
C5 C 0.22705(16) 0.4393(5) 0.2606(3) 0.0376(9) Uani 1 1 d . . .
H5A H 0.1910 0.5218 0.2860 0.045 Uiso 1 1 calc R . .
H5B H 0.2310 0.4605 0.1760 0.045 Uiso 1 1 calc R . .
C6 C 0.17000(15) 0.0571(5) 0.2523(3) 0.0359(9) Uani 1 1 d . . .
H6A H 0.1798 -0.0967 0.2783 0.043 Uiso 1 1 calc R . .
C7 C 0.10984(16) 0.1238(5) 0.3099(4) 0.0434(10) Uani 1 1 d . . .
H7A H 0.0990 0.2773 0.2885 0.052 Uiso 1 1 calc R . .
H7B H 0.1158 0.1162 0.3956 0.052 Uiso 1 1 calc R . .
C8 C 0.05682(17) -0.0352(5) 0.2684(4) 0.0482(11) Uani 1 1 d . . .
H8A H 0.0662 -0.1861 0.2966 0.058 Uiso 1 1 calc R . .
H8B H 0.0183 0.0125 0.3027 0.058 Uiso 1 1 calc R . .
C9 C 0.04784(18) -0.0384(6) 0.1343(4) 0.0485(11) Uani 1 1 d . . .
H9A H 0.0154 -0.1455 0.1110 0.058 Uiso 1 1 calc R . .
H9B H 0.0346 0.1091 0.1063 0.058 Uiso 1 1 calc R . .
C10 C 0.10788(17) -0.1027(6) 0.0784(4) 0.0477(10) Uani 1 1 d . . .
H10A H 0.1021 -0.0943 -0.0073 0.057 Uiso 1 1 calc R . .
H10B H 0.1183 -0.2568 0.0993 0.057 Uiso 1 1 calc R . .
C11 C 0.16181(17) 0.0514(5) 0.1192(4) 0.0449(10) Uani 1 1 d . . .
H11A H 0.2001 -0.0015 0.0860 0.054 Uiso 1 1 calc R . .
H11B H 0.1537 0.2023 0.0898 0.054 Uiso 1 1 calc R . .
C12 C 0.33444(16) 0.3506(5) 0.5270(3) 0.0365(9) Uani 1 1 d . . .
H12A H 0.3185 0.2566 0.5902 0.044 Uiso 1 1 calc R . .
C13 C 0.39560(16) 0.2443(5) 0.4907(3) 0.0417(10) Uani 1 1 d . . .
H13A H 0.3874 0.0952 0.4589 0.050 Uiso 1 1 calc R . .
H13B H 0.4133 0.3344 0.4290 0.050 Uiso 1 1 calc R . .
C14 C 0.44228(17) 0.2280(5) 0.5969(4) 0.0461(11) Uani 1 1 d . . .
H14A H 0.4815 0.1691 0.5707 0.055 Uiso 1 1 calc R . .
H14B H 0.4265 0.1243 0.6547 0.055 Uiso 1 1 calc R . .
C15 C 0.45349(16) 0.4570(5) 0.6551(4) 0.0453(10) Uani 1 1 d . . .
H15A H 0.4799 0.4388 0.7266 0.054 Uiso 1 1 calc R . .
H15B H 0.4750 0.5542 0.6013 0.054 Uiso 1 1 calc R . .
C16 C 0.39223(17) 0.5657(5) 0.6863(4) 0.0456(10) Uani 1 1 d . . .
H16A H 0.3734 0.4780 0.7478 0.055 Uiso 1 1 calc R . .
H16B H 0.4005 0.7151 0.7177 0.055 Uiso 1 1 calc R . .
C17 C 0.34664(16) 0.5829(5) 0.5799(4) 0.0419(10) Uani 1 1 d . . .
H17A H 0.3637 0.6806 0.5207 0.050 Uiso 1 1 calc R . .
H17B H 0.3077 0.6477 0.6041 0.050 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
N1 0.0388(17) 0.0335(15) 0.035(2) 0.0006(12) -0.0057(16) -0.0004(11)
C2 0.0334(19) 0.0372(19) 0.037(3) 0.0010(17) -0.0005(19) 0.0035(14)
O2 0.0486(16) 0.0359(13) 0.0411(19) 0.0033(11) -0.0068(13) -0.0012(9)
N3 0.0415(17) 0.0334(14) 0.031(2) 0.0006(13) -0.0036(16) -0.0020(11)
C4 0.046(2) 0.0397(19) 0.029(3) -0.0016(15) -0.0034(19) -0.0013(14)
C5 0.044(2) 0.0367(18) 0.032(3) 0.0012(15) -0.0026(18) 0.0035(14)
C6 0.039(2) 0.0335(17) 0.035(3) -0.0014(15) -0.0037(19) -0.0008(13)
C7 0.040(2) 0.052(2) 0.037(3) -0.0046(17) -0.0053(19) -0.0069(15)
C8 0.040(2) 0.060(2) 0.044(3) -0.0010(18) -0.003(2) -0.0039(16)
C9 0.046(2) 0.053(2) 0.045(3) 0.0005(18) -0.012(2) -0.0035(16)
C10 0.045(2) 0.060(2) 0.036(3) -0.0052(17) -0.011(2) -0.0046(16)
C11 0.042(2) 0.058(2) 0.035(3) -0.0043(18) 0.0011(19) -0.0034(16)
C12 0.041(2) 0.0392(18) 0.029(3) -0.0015(15) -0.0030(19) -0.0033(14)
C13 0.045(2) 0.0405(18) 0.039(3) -0.0038(16) -0.004(2) 0.0048(14)
C14 0.044(2) 0.048(2) 0.045(3) -0.0060(16) -0.008(2) 0.0059(15)
C15 0.042(2) 0.056(2) 0.037(3) -0.0019(17) -0.010(2) -0.0032(15)
C16 0.049(2) 0.0427(19) 0.044(3) -0.0069(17) -0.005(2) -0.0015(15)
C17 0.043(2) 0.0416(19) 0.040(3) -0.0036(15) -0.005(2) 0.0036(14)

_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
N1 C2 1.364(5) . ?
N1 C6 1.474(4) . ?
N1 C5 1.475(4) . ?
C2 O2 1.244(4) . ?
C2 N3 1.374(4) . ?
N3 C12 1.451(5) . ?
N3 C4 1.459(4) . ?
C4 C5 1.521(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C11 1.504(5) . ?
C6 C7 1.523(5) . ?
C6 H6A 0.9800 . ?
C7 C8 1.535(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.516(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.508(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.529(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C17 1.523(4) . ?
C12 C13 1.528(4) . ?
C12 H12A 0.9800 . ?
C13 C14 1.528(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.526(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.520(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.516(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 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
C2 N1 C6 120.6(3) . . ?
C2 N1 C5 108.8(3) . . ?
C6 N1 C5 122.2(3) . . ?
O2 C2 N1 125.7(3) . . ?
O2 C2 N3 124.8(4) . . ?
N1 C2 N3 109.5(3) . . ?
C2 N3 C12 121.7(3) . . ?
C2 N3 C4 109.0(3) . . ?
C12 N3 C4 124.6(3) . . ?
N3 C4 C5 102.2(3) . . ?
N3 C4 H4A 111.3 . . ?
C5 C4 H4A 111.3 . . ?
N3 C4 H4B 111.3 . . ?
C5 C4 H4B 111.3 . . ?
H4A C4 H4B 109.2 . . ?
N1 C5 C4 101.0(3) . . ?
N1 C5 H5A 111.6 . . ?
C4 C5 H5A 111.6 . . ?
N1 C5 H5B 111.6 . . ?
C4 C5 H5B 111.6 . . ?
H5A C5 H5B 109.4 . . ?
N1 C6 C11 111.5(3) . . ?
N1 C6 C7 112.5(3) . . ?
C11 C6 C7 111.7(3) . . ?
N1 C6 H6A 106.9 . . ?
C11 C6 H6A 106.9 . . ?
C7 C6 H6A 106.9 . . ?
C6 C7 C8 109.8(3) . . ?
C6 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
C6 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C7 111.8(3) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 110.4(3) . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C9 C10 C11 111.8(3) . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
C6 C11 C10 111.5(3) . . ?
C6 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C6 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
N3 C12 C17 112.2(3) . . ?
N3 C12 C13 113.2(3) . . ?
C17 C12 C13 110.2(3) . . ?
N3 C12 H12A 106.9 . . ?
C17 C12 H12A 106.9 . . ?
C13 C12 H12A 106.9 . . ?
C14 C13 C12 110.9(3) . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 C15 111.4(3) . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 111.0(3) . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C17 C16 C15 112.2(3) . . ?
C17 C16 H16A 109.2 . . ?
C15 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 C12 110.0(3) . . ?
C16 C17 H17A 109.7 . . ?
C12 C17 H17A 109.7 . . ?
C16 C17 H17B 109.7 . . ?
C12 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 O2 18.6(5) . . . . ?
C5 N1 C2 O2 167.3(3) . . . . ?
C6 N1 C2 N3 -161.7(2) . . . . ?
C5 N1 C2 N3 -12.9(3) . . . . ?
O2 C2 N3 C12 15.3(5) . . . . ?
N1 C2 N3 C12 -164.5(3) . . . . ?
O2 C2 N3 C4 171.9(3) . . . . ?
N1 C2 N3 C4 -7.8(3) . . . . ?
C2 N3 C4 C5 24.1(3) . . . . ?
C12 N3 C4 C5 179.9(3) . . . . ?
C2 N1 C5 C4 26.9(3) . . . . ?
C6 N1 C5 C4 175.0(3) . . . . ?
N3 C4 C5 N1 -29.6(3) . . . . ?
C2 N1 C6 C11 -156.5(3) . . . . ?
C5 N1 C6 C11 59.0(4) . . . . ?
C2 N1 C6 C7 77.1(4) . . . . ?
C5 N1 C6 C7 -67.4(4) . . . . ?
N1 C6 C7 C8 -178.1(3) . . . . ?
C11 C6 C7 C8 55.5(4) . . . . ?
C6 C7 C8 C9 -56.4(4) . . . . ?
C7 C8 C9 C10 56.6(4) . . . . ?
C8 C9 C10 C11 -55.2(4) . . . . ?
N1 C6 C11 C10 177.9(3) . . . . ?
C7 C6 C11 C10 -55.2(3) . . . . ?
C9 C10 C11 C6 55.0(4) . . . . ?
C2 N3 C12 C17 -156.3(3) . . . . ?
C4 N3 C12 C17 50.8(4) . . . . ?
C2 N3 C12 C13 78.2(4) . . . . ?
C4 N3 C12 C13 -74.7(4) . . . . ?
N3 C12 C13 C14 -175.6(3) . . . . ?
C17 C12 C13 C14 57.8(4) . . . . ?
C12 C13 C14 C15 -55.4(4) . . . . ?
C13 C14 C15 C16 53.4(4) . . . . ?
C14 C15 C16 C17 -54.7(4) . . . . ?
C15 C16 C17 C12 57.2(4) . . . . ?
N3 C12 C17 C16 174.7(3) . . . . ?
C13 C12 C17 C16 -58.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.060