# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cu-mn1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H34 Cu N6 O2'
_chemical_formula_sum            'C30 H34 Cu N6 O2'
_chemical_formula_weight         574.18

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'
Cu Cu 0.3201 1.2651 '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 2/c'
_symmetry_space_group_name_hall  '-C 2yc'
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'
'-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                   21.536
_cell_length_b                   9.920
_cell_length_c                   13.033
_cell_angle_alpha                90.00
_cell_angle_beta                 108.98
_cell_angle_gamma                90.00
_cell_volume                     2632.954
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.49

_exptl_crystal_description       Rod-shape
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1204
_exptl_absorpt_coefficient_mu    0.870
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.778
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5843
_diffrn_reflns_av_R_equivalents  0.0133
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3028
_reflns_number_gt                2734
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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^)+(0.0902P)^2^+0.6348P] 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    ref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3028
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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
Cu1 Cu 0.5000 0.49997(2) 0.2500 0.01230(14) Uani 1 2 d S . .
O1 O 0.53027(6) 0.63652(12) 0.17583(9) 0.0168(2) Uani 1 1 d . . .
N1 N 0.53568(6) 0.35529(14) 0.18590(11) 0.0140(3) Uani 1 1 d . . .
N2 N 0.61832(6) 0.95612(13) 0.16986(9) 0.0136(3) Uani 1 1 d . . .
N3 N 0.65175(6) 1.04371(14) 0.12628(10) 0.0174(3) Uani 1 1 d . . .
C1 C 0.56694(8) 0.36799(17) 0.11694(12) 0.0155(3) Uani 1 1 d . . .
H1 H 0.5807(11) 0.287(2) 0.0948(17) 0.025(5) Uiso 1 1 d . . .
C2 C 0.58373(9) 0.49434(13) 0.07886(15) 0.0143(4) Uani 1 1 d . . .
C3 C 0.56532(7) 0.62175(16) 0.11070(12) 0.0134(3) Uani 1 1 d . . .
C4 C 0.58663(7) 0.73896(15) 0.06933(11) 0.0132(3) Uani 1 1 d . . .
C5 C 0.62516(7) 0.72819(15) 0.00252(11) 0.0151(3) Uani 1 1 d . . .
H5 H 0.6400(10) 0.810(2) -0.0236(16) 0.024(5) Uiso 1 1 d . . .
C6 C 0.64346(7) 0.60326(16) -0.02963(12) 0.0171(3) Uani 1 1 d . . .
C7 C 0.62197(9) 0.48942(15) 0.00853(15) 0.0165(4) Uani 1 1 d . . .
H7 H 0.6323(11) 0.406(2) -0.0083(17) 0.027(5) Uiso 1 1 d . . .
C8 C 0.68543(9) 0.59595(18) -0.10266(14) 0.0237(4) Uani 1 1 d . . .
H8A H 0.6782(13) 0.661(3) -0.150(2) 0.058(8) Uiso 1 1 d . . .
H8B H 0.7293(17) 0.578(3) -0.068(2) 0.070(9) Uiso 1 1 d . . .
H8C H 0.6638(19) 0.526(3) -0.169(3) 0.072(11) Uiso 1 1 d . . .
C9 C 0.56542(7) 0.87589(15) 0.09657(11) 0.0140(3) Uani 1 1 d . . .
H9A H 0.5304(9) 0.869(2) 0.1273(14) 0.017(4) Uiso 1 1 d . . .
H9B H 0.5495(9) 0.9268(18) 0.0302(14) 0.016(4) Uiso 1 1 d . . .
C10 C 0.64212(7) 0.95234(15) 0.27975(11) 0.0159(3) Uani 1 1 d . . .
C11 C 0.69401(8) 1.04246(18) 0.30937(13) 0.0199(3) Uani 1 1 d . . .
H11 H 0.7200(11) 1.055(2) 0.3776(18) 0.032(5) Uiso 1 1 d . . .
C12 C 0.69805(8) 1.09646(15) 0.21223(12) 0.0197(3) Uani 1 1 d . . .
C13 C 0.61335(10) 0.8661(2) 0.34618(13) 0.0274(4) Uani 1 1 d . . .
H13A H 0.6341(11) 0.883(2) 0.4214(19) 0.041(6) Uiso 1 1 d . . .
H13B H 0.6167(13) 0.778(3) 0.330(2) 0.055(8) Uiso 1 1 d . . .
H13C H 0.5717(14) 0.892(3) 0.336(2) 0.052(7) Uiso 1 1 d . . .
C14 C 0.74403(10) 1.20138(19) 0.19713(16) 0.0296(4) Uani 1 1 d . . .
H14A H 0.7318(14) 1.287(3) 0.209(2) 0.065(8) Uiso 1 1 d . . .
H14B H 0.7871(13) 1.179(2) 0.2374(19) 0.042(6) Uiso 1 1 d . . .
H14C H 0.7410(11) 1.211(2) 0.120(2) 0.039(6) Uiso 1 1 d . . .
C15 C 0.52888(8) 0.22057(15) 0.22809(12) 0.0176(3) Uani 1 1 d . . .
H15A H 0.5709(11) 0.202(2) 0.2847(18) 0.035(6) Uiso 1 1 d . . .
H15B H 0.5192(10) 0.155(2) 0.1691(16) 0.023(5) Uiso 1 1 d . . .

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 0.01498(19) 0.0085(2) 0.01556(19) 0.000 0.00794(13) 0.000
O1 0.0225(6) 0.0119(5) 0.0219(5) -0.0005(4) 0.0152(5) -0.0002(4)
N1 0.0158(6) 0.0095(6) 0.0160(6) -0.0003(5) 0.0045(5) 0.0001(5)
N2 0.0171(6) 0.0114(6) 0.0139(6) -0.0006(5) 0.0073(5) -0.0006(5)
N3 0.0213(7) 0.0140(6) 0.0200(6) -0.0007(5) 0.0112(5) -0.0025(5)
C1 0.0167(7) 0.0125(7) 0.0168(7) -0.0032(6) 0.0048(6) 0.0021(6)
C2 0.0140(8) 0.0152(9) 0.0139(8) -0.0018(4) 0.0050(6) -0.0005(5)
C3 0.0127(7) 0.0142(7) 0.0134(6) -0.0014(5) 0.0045(5) -0.0003(5)
C4 0.0122(7) 0.0134(7) 0.0133(6) -0.0017(5) 0.0033(5) 0.0013(5)
C5 0.0153(7) 0.0173(7) 0.0136(6) 0.0004(5) 0.0059(5) -0.0007(5)
C6 0.0159(7) 0.0211(8) 0.0156(6) -0.0010(6) 0.0070(5) 0.0014(6)
C7 0.0179(8) 0.0164(9) 0.0170(8) -0.0041(5) 0.0080(7) 0.0029(5)
C8 0.0275(9) 0.0252(9) 0.0250(8) 0.0011(7) 0.0173(7) 0.0055(7)
C9 0.0137(7) 0.0129(7) 0.0154(6) -0.0005(5) 0.0049(5) -0.0005(5)
C10 0.0191(7) 0.0139(8) 0.0147(7) -0.0021(6) 0.0055(5) 0.0033(6)
C11 0.0183(8) 0.0193(8) 0.0198(8) -0.0065(6) 0.0032(6) 0.0012(7)
C12 0.0183(7) 0.0152(7) 0.0268(8) -0.0046(6) 0.0087(6) -0.0002(6)
C13 0.0359(10) 0.0311(10) 0.0171(7) 0.0013(7) 0.0112(7) -0.0048(8)
C14 0.0283(10) 0.0241(9) 0.0409(10) -0.0087(7) 0.0174(8) -0.0099(7)
C15 0.0235(8) 0.0099(7) 0.0204(7) 0.0016(5) 0.0085(6) 0.0028(6)

_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 O1 1.8984(12) 2_655 ?
Cu1 O1 1.8984(12) . ?
Cu1 N1 1.9405(14) . ?
Cu1 N1 1.9405(14) 2_655 ?
O1 C3 1.3148(19) . ?
N1 C1 1.292(2) . ?
N1 C15 1.4704(19) . ?
N2 C10 1.3557(18) . ?
N2 N3 1.3645(19) . ?
N2 C9 1.4615(18) . ?
N3 C12 1.3403(19) . ?
C1 C2 1.437(2) . ?
C1 H1 0.93(2) . ?
C2 C7 1.418(3) . ?
C2 C3 1.426(2) . ?
C3 C4 1.419(2) . ?
C4 C5 1.388(2) . ?
C4 C9 1.5117(19) . ?
C5 C6 1.405(2) . ?
C5 H5 0.97(2) . ?
C6 C7 1.373(2) . ?
C6 C8 1.512(2) . ?
C7 H7 0.91(2) . ?
C8 H8A 0.87(3) . ?
C8 H8B 0.92(3) . ?
C8 H8C 1.09(4) . ?
C9 H9A 0.96(2) . ?
C9 H9B 0.964(18) . ?
C10 C11 1.384(2) . ?
C10 C13 1.488(2) . ?
C11 C12 1.403(2) . ?
C11 H11 0.89(2) . ?
C12 C14 1.493(2) . ?
C13 H13A 0.95(2) . ?
C13 H13B 0.90(3) . ?
C13 H13C 0.90(3) . ?
C14 H14A 0.91(3) . ?
C14 H14B 0.93(3) . ?
C14 H14C 0.99(2) . ?
C15 C15 1.528(3) 2_655 ?
C15 H15A 0.98(2) . ?
C15 H15B 0.98(2) . ?

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 Cu1 O1 88.95(7) 2_655 . ?
O1 Cu1 N1 175.22(4) 2_655 . ?
O1 Cu1 N1 93.38(7) . . ?
O1 Cu1 N1 93.38(7) 2_655 2_655 ?
O1 Cu1 N1 175.22(4) . 2_655 ?
N1 Cu1 N1 84.61(8) . 2_655 ?
C3 O1 Cu1 127.84(11) . . ?
C1 N1 C15 119.11(14) . . ?
C1 N1 Cu1 126.58(12) . . ?
C15 N1 Cu1 114.18(10) . . ?
C10 N2 N3 112.83(12) . . ?
C10 N2 C9 128.46(13) . . ?
N3 N2 C9 118.65(11) . . ?
C12 N3 N2 104.51(12) . . ?
N1 C1 C2 124.87(16) . . ?
N1 C1 H1 114.8(13) . . ?
C2 C1 H1 120.2(13) . . ?
C7 C2 C3 119.56(14) . . ?
C7 C2 C1 117.22(14) . . ?
C3 C2 C1 123.20(19) . . ?
O1 C3 C4 118.59(14) . . ?
O1 C3 C2 123.98(15) . . ?
C4 C3 C2 117.43(15) . . ?
C5 C4 C3 120.54(14) . . ?
C5 C4 C9 120.28(14) . . ?
C3 C4 C9 119.15(13) . . ?
C4 C5 C6 122.53(14) . . ?
C4 C5 H5 119.3(12) . . ?
C6 C5 H5 118.2(12) . . ?
C7 C6 C5 117.19(14) . . ?
C7 C6 C8 121.95(15) . . ?
C5 C6 C8 120.86(14) . . ?
C6 C7 C2 122.72(14) . . ?
C6 C7 H7 122.0(14) . . ?
C2 C7 H7 115.3(13) . . ?
C6 C8 H8A 114.1(19) . . ?
C6 C8 H8B 115.5(18) . . ?
H8A C8 H8B 114(3) . . ?
C6 C8 H8C 110(2) . . ?
H8A C8 H8C 89(2) . . ?
H8B C8 H8C 111(3) . . ?
N2 C9 C4 114.32(11) . . ?
N2 C9 H9A 108.3(11) . . ?
C4 C9 H9A 111.9(12) . . ?
N2 C9 H9B 106.0(11) . . ?
C4 C9 H9B 107.9(11) . . ?
H9A C9 H9B 108.1(15) . . ?
N2 C10 C11 105.68(14) . . ?
N2 C10 C13 123.00(14) . . ?
C11 C10 C13 131.31(14) . . ?
C10 C11 C12 106.03(14) . . ?
C10 C11 H11 123.9(15) . . ?
C12 C11 H11 129.9(15) . . ?
N3 C12 C11 110.95(14) . . ?
N3 C12 C14 120.47(15) . . ?
C11 C12 C14 128.56(15) . . ?
C10 C13 H13A 110.6(14) . . ?
C10 C13 H13B 109.9(16) . . ?
H13A C13 H13B 111(2) . . ?
C10 C13 H13C 109.3(17) . . ?
H13A C13 H13C 102(2) . . ?
H13B C13 H13C 113(2) . . ?
C12 C14 H14A 112.7(19) . . ?
C12 C14 H14B 110.1(15) . . ?
H14A C14 H14B 114(2) . . ?
C12 C14 H14C 111.9(13) . . ?
H14A C14 H14C 99(2) . . ?
H14B C14 H14C 109(2) . . ?
N1 C15 C15 109.39(9) . 2_655 ?
N1 C15 H15A 105.7(13) . . ?
C15 C15 H15A 112.5(13) 2_655 . ?
N1 C15 H15B 109.5(12) . . ?
C15 C15 H15B 107.6(12) 2_655 . ?
H15A C15 H15B 112.1(17) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.745
_refine_diff_density_rms         0.184
_database_code_depnum_ccdc_archive 'CCDC 905948'