# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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_Complex

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H19 Cu N3 O2'
_chemical_formula_sum            'C17 H19 Cu N3 O2'
_chemical_formula_weight         360.89

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'
Cu Cu 0.3201 1.2651 '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           orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   8.2090(5)
_cell_length_b                   9.1718(6)
_cell_length_c                   20.3772(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1534.23(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    2524
_cell_measurement_theta_min      2.4270
_cell_measurement_theta_max      29.9450

_exptl_crystal_description       block
_exptl_crystal_colour            dark-blue
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748
_exptl_absorpt_coefficient_mu    1.437
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_T_max  0.810
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       n/a
_diffrn_detector_area_resol_mean 8.0053
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4550
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0512
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         28.00
_reflns_number_total             3262
_reflns_number_gt                3107
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    
;
SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0260P)²+0.0000P] where P=(Fo²+2Fc²)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(14)
_refine_ls_number_reflns         3262
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0715
_refine_ls_wR_factor_gt          0.0688
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 -0.57156(4) -0.52113(4) -0.490150(14) 0.01871(9) Uani 1 1 d . . .
O1 O -0.3929(2) -0.4998(2) -0.43176(8) 0.0235(4) Uani 1 1 d . . .
O2 O -0.1830(2) -0.7544(2) -0.56498(11) 0.0339(6) Uani 1 1 d . . .
N1 N -0.7028(3) -0.3841(3) -0.43855(11) 0.0206(5) Uani 1 1 d . . .
N2 N -0.7549(2) -0.5048(3) -0.55853(10) 0.0190(5) Uani 1 1 d . . .
N3 N -0.4314(3) -0.6254(3) -0.55161(11) 0.0273(5) Uani 1 1 d . . .
C1 C -0.0806(4) -0.4198(3) -0.23751(13) 0.0281(6) Uani 1 1 d . . .
H1 H -0.0692 -0.3800 -0.1947 0.034 Uiso 1 1 calc R . .
C2 C 0.0477(3) -0.4909(3) -0.26572(13) 0.0276(6) Uani 1 1 d . . .
H2 H 0.1470 -0.5012 -0.2422 0.033 Uiso 1 1 calc R . .
C3 C 0.0338(3) -0.5491(3) -0.32933(13) 0.0261(7) Uani 1 1 d . . .
H3 H 0.1237 -0.5978 -0.3489 0.031 Uiso 1 1 calc R . .
C4 C -0.1101(3) -0.5354(3) -0.36307(13) 0.0224(6) Uani 1 1 d . . .
H4 H -0.1192 -0.5756 -0.4059 0.027 Uiso 1 1 calc R . .
C5 C -0.2436(3) -0.4632(3) -0.33535(12) 0.0200(6) Uani 1 1 d . . .
C6 C -0.3929(3) -0.4443(3) -0.37298(12) 0.0197(6) Uani 1 1 d . . .
C7 C -0.5202(3) -0.3618(3) -0.34584(13) 0.0215(6) Uani 1 1 d . . .
C8 C -0.5032(4) -0.3100(4) -0.27983(14) 0.0277(7) Uani 1 1 d . . .
H8 H -0.5922 -0.2598 -0.2604 0.033 Uiso 1 1 calc R . .
C9 C -0.3671(4) -0.3290(4) -0.24412(14) 0.0301(7) Uani 1 1 d . . .
H9 H -0.3617 -0.2920 -0.2006 0.036 Uiso 1 1 calc R . .
C10 C -0.2303(3) -0.4047(3) -0.27124(13) 0.0225(6) Uani 1 1 d . . .
C11 C -0.6636(3) -0.3210(3) -0.38352(14) 0.0219(6) Uani 1 1 d . . .
C12 C -0.7654(3) -0.1956(4) -0.35828(15) 0.0301(7) Uani 1 1 d . . .
H12A H -0.8601 -0.2338 -0.3346 0.045 Uiso 1 1 calc R . .
H12B H -0.8024 -0.1360 -0.3953 0.045 Uiso 1 1 calc R . .
H12C H -0.6997 -0.1356 -0.3286 0.045 Uiso 1 1 calc R . .
C13 C -0.8533(3) -0.3407(3) -0.47250(14) 0.0255(6) Uani 1 1 d . . .
H13A H -0.8360 -0.2481 -0.4965 0.031 Uiso 1 1 calc R . .
H13B H -0.9422 -0.3260 -0.4403 0.031 Uiso 1 1 calc R . .
C14 C -0.8984(3) -0.4611(3) -0.52012(13) 0.0244(6) Uani 1 1 d . . .
H14A H -0.9407 -0.5461 -0.4956 0.029 Uiso 1 1 calc R . .
H14B H -0.9851 -0.4265 -0.5500 0.029 Uiso 1 1 calc R . .
C15 C -0.7064(3) -0.3906(3) -0.60550(14) 0.0246(6) Uani 1 1 d . . .
H15A H -0.6876 -0.2990 -0.5819 0.037 Uiso 1 1 calc R . .
H15B H -0.7932 -0.3768 -0.6379 0.037 Uiso 1 1 calc R . .
H15C H -0.6060 -0.4202 -0.6279 0.037 Uiso 1 1 calc R . .
C16 C -0.7925(4) -0.6390(3) -0.59610(15) 0.0259(6) Uani 1 1 d . . .
H16A H -0.6963 -0.6686 -0.6213 0.039 Uiso 1 1 calc R . .
H16B H -0.8831 -0.6199 -0.6262 0.039 Uiso 1 1 calc R . .
H16C H -0.8228 -0.7171 -0.5657 0.039 Uiso 1 1 calc R . .
C17 C -0.3076(3) -0.6880(3) -0.55651(13) 0.0218(6) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.8986(17) . ?
Cu1 N3 1.951(2) . ?
Cu1 N1 1.961(2) . ?
Cu1 N2 2.056(2) . ?
O1 C6 1.302(3) . ?
O2 C17 1.203(3) . ?
N1 C11 1.302(4) . ?
N1 C13 1.471(3) . ?
N2 C14 1.470(3) . ?
N2 C15 1.474(3) . ?
N2 C16 1.482(4) . ?
N3 C17 1.171(4) . ?
C1 C2 1.366(4) . ?
C1 C10 1.415(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.406(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.372(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.400(4) . ?
C4 H4 0.9500 . ?
C5 C10 1.417(4) . ?
C5 C6 1.456(3) . ?
C6 C7 1.404(4) . ?
C7 C8 1.434(4) . ?
C7 C11 1.454(4) . ?
C8 C9 1.345(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.431(4) . ?
C9 H9 0.9500 . ?
C11 C12 1.512(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.516(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 N3 89.84(9) . . ?
O1 Cu1 N1 91.28(9) . . ?
N3 Cu1 N1 169.19(10) . . ?
O1 Cu1 N2 169.23(9) . . ?
N3 Cu1 N2 91.86(9) . . ?
N1 Cu1 N2 85.09(9) . . ?
C6 O1 Cu1 128.09(16) . . ?
C11 N1 C13 119.5(2) . . ?
C11 N1 Cu1 127.6(2) . . ?
C13 N1 Cu1 112.50(17) . . ?
C14 N2 C15 111.6(2) . . ?
C14 N2 C16 109.6(2) . . ?
C15 N2 C16 108.1(2) . . ?
C14 N2 Cu1 104.21(15) . . ?
C15 N2 Cu1 107.11(16) . . ?
C16 N2 Cu1 116.22(17) . . ?
C17 N3 Cu1 143.8(2) . . ?
C2 C1 C10 120.8(2) . . ?
C2 C1 H1 119.6 . . ?
C10 C1 H1 119.6 . . ?
C1 C2 C3 120.4(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 121.0(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C10 119.4(2) . . ?
C4 C5 C6 120.2(2) . . ?
C10 C5 C6 120.3(2) . . ?
O1 C6 C7 125.0(2) . . ?
O1 C6 C5 116.0(2) . . ?
C7 C6 C5 118.9(2) . . ?
C6 C7 C8 118.4(3) . . ?
C6 C7 C11 122.2(2) . . ?
C8 C7 C11 119.3(3) . . ?
C9 C8 C7 123.1(3) . . ?
C9 C8 H8 118.5 . . ?
C7 C8 H8 118.5 . . ?
C8 C9 C10 120.4(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C1 C10 C5 118.5(3) . . ?
C1 C10 C9 122.8(3) . . ?
C5 C10 C9 118.7(2) . . ?
N1 C11 C7 122.7(2) . . ?
N1 C11 C12 119.6(3) . . ?
C7 C11 C12 117.6(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 108.0(2) . . ?
N1 C13 H13A 110.1 . . ?
C14 C13 H13A 110.1 . . ?
N1 C13 H13B 110.1 . . ?
C14 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
N2 C14 C13 110.1(2) . . ?
N2 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
N2 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 O2 176.4(3) . . ?

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
N3 Cu1 O1 C6 -175.2(2) . . . . ?
N1 Cu1 O1 C6 15.6(2) . . . . ?
N2 Cu1 O1 C6 85.7(5) . . . . ?
O1 Cu1 N1 C11 -3.8(2) . . . . ?
N3 Cu1 N1 C11 -99.7(5) . . . . ?
N2 Cu1 N1 C11 -173.6(3) . . . . ?
O1 Cu1 N1 C13 169.16(19) . . . . ?
N3 Cu1 N1 C13 73.3(6) . . . . ?
N2 Cu1 N1 C13 -0.69(18) . . . . ?
O1 Cu1 N2 C14 -95.1(4) . . . . ?
N3 Cu1 N2 C14 165.98(17) . . . . ?
N1 Cu1 N2 C14 -24.41(17) . . . . ?
O1 Cu1 N2 C15 23.4(5) . . . . ?
N3 Cu1 N2 C15 -75.60(18) . . . . ?
N1 Cu1 N2 C15 94.01(17) . . . . ?
O1 Cu1 N2 C16 144.3(4) . . . . ?
N3 Cu1 N2 C16 45.34(19) . . . . ?
N1 Cu1 N2 C16 -145.05(19) . . . . ?
O1 Cu1 N3 C17 17.5(4) . . . . ?
N1 Cu1 N3 C17 113.5(6) . . . . ?
N2 Cu1 N3 C17 -173.1(4) . . . . ?
C10 C1 C2 C3 0.7(4) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C10 -0.6(4) . . . . ?
C3 C4 C5 C6 177.4(3) . . . . ?
Cu1 O1 C6 C7 -13.7(4) . . . . ?
Cu1 O1 C6 C5 170.45(18) . . . . ?
C4 C5 C6 O1 1.0(4) . . . . ?
C10 C5 C6 O1 178.9(2) . . . . ?
C4 C5 C6 C7 -175.2(3) . . . . ?
C10 C5 C6 C7 2.8(4) . . . . ?
O1 C6 C7 C8 179.0(3) . . . . ?
C5 C6 C7 C8 -5.2(4) . . . . ?
O1 C6 C7 C11 -4.4(4) . . . . ?
C5 C6 C7 C11 171.4(3) . . . . ?
C6 C7 C8 C9 4.2(5) . . . . ?
C11 C7 C8 C9 -172.5(3) . . . . ?
C7 C8 C9 C10 -0.4(5) . . . . ?
C2 C1 C10 C5 -0.9(4) . . . . ?
C2 C1 C10 C9 -178.9(3) . . . . ?
C4 C5 C10 C1 0.8(4) . . . . ?
C6 C5 C10 C1 -177.2(3) . . . . ?
C4 C5 C10 C9 178.9(3) . . . . ?
C6 C5 C10 C9 1.0(4) . . . . ?
C8 C9 C10 C1 175.9(3) . . . . ?
C8 C9 C10 C5 -2.2(5) . . . . ?
C13 N1 C11 C7 177.6(2) . . . . ?
Cu1 N1 C11 C7 -9.9(4) . . . . ?
C13 N1 C11 C12 -5.1(4) . . . . ?
Cu1 N1 C11 C12 167.4(2) . . . . ?
C6 C7 C11 N1 16.4(4) . . . . ?
C8 C7 C11 N1 -167.0(3) . . . . ?
C6 C7 C11 C12 -160.9(3) . . . . ?
C8 C7 C11 C12 15.7(4) . . . . ?
C11 N1 C13 C14 -161.1(2) . . . . ?
Cu1 N1 C13 C14 25.3(3) . . . . ?
C15 N2 C14 C13 -70.3(3) . . . . ?
C16 N2 C14 C13 170.0(2) . . . . ?
Cu1 N2 C14 C13 45.0(2) . . . . ?
N1 C13 C14 N2 -47.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.062
_database_code_depnum_ccdc_archive 'CCDC 1019456'
