# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu
_database_code_depnum_ccdc_archive 'CCDC 1015117'
_audit_update_record             
;
2014-07-19 deposited with the CCDC.
2015-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H N O'
_chemical_formula_weight         43.03

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           ?
_symmetry_space_group_name_H-M   ?

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                   17.662(10)
_cell_length_b                   16.526(9)
_cell_length_c                   7.599(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.592(9)
_cell_angle_gamma                90.00
_cell_volume                     2199(2)
_cell_formula_units_Z            44
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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_reflns_number            15358
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_sigmaI/netI    0.0612
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.16
_diffrn_reflns_theta_max         25.36
_reflns_number_total             3938
_reflns_number_gt                1915
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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 > 2sigma(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)+(0.1000P)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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.034(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3938
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1440
_refine_ls_R_factor_gt           0.0650
_refine_ls_wR_factor_ref         0.2140
_refine_ls_wR_factor_gt          0.1449
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
O1 O 1.03232(12) 0.59657(15) 0.3278(3) 0.0713(7) Uani 1 1 d . . .
H1 H 1.0783 0.5953 0.3625 0.107 Uiso 1 1 calc R . .
N3 N 1.17052(14) 0.53884(19) 0.3680(4) 0.0625(8) Uani 1 1 d . . .
C3 C 1.00903(18) 0.5229(2) 0.2650(4) 0.0554(9) Uani 1 1 d . . .
N4 N 0.81308(14) 0.57737(16) 0.0990(4) 0.0604(8) Uani 1 1 d . . .
C5 C 1.06049(17) 0.4586(2) 0.2631(4) 0.0557(9) Uani 1 1 d . . .
C6 C 0.93239(17) 0.5122(2) 0.1962(4) 0.0536(9) Uani 1 1 d . . .
C7 C 0.90873(17) 0.4374(2) 0.1283(4) 0.0577(9) Uani 1 1 d . . .
H7 H 0.8579 0.4310 0.0797 0.069 Uiso 1 1 calc R . .
C8 C 0.68946(17) 0.6421(2) 0.0840(4) 0.0559(9) Uani 1 1 d . . .
C9 C 1.03339(18) 0.3843(2) 0.1978(5) 0.0604(9) Uani 1 1 d . . .
H9 H 1.0674 0.3413 0.1998 0.072 Uiso 1 1 calc R . .
C10 C 1.28324(17) 0.5988(2) 0.5325(4) 0.0563(9) Uani 1 1 d . . .
C33 C 1.14166(18) 0.4711(2) 0.3135(5) 0.0641(10) Uani 1 1 d . . .
H33 H 1.1744 0.4276 0.3056 0.077 Uiso 1 1 calc R . .
C12 C 0.76903(18) 0.6494(2) 0.0754(4) 0.0573(9) Uani 1 1 d . . .
C34 C 0.88037(18) 0.5814(2) 0.1844(4) 0.0605(9) Uani 1 1 d . . .
H34 H 0.8966 0.6295 0.2406 0.073 Uiso 1 1 calc R . .
C14 C 0.79862(19) 0.7223(2) 0.0325(4) 0.0655(10) Uani 1 1 d . . .
H14 H 0.8506 0.7265 0.0249 0.079 Uiso 1 1 calc R . .
C15 C 1.25166(17) 0.5471(2) 0.3959(5) 0.0616(10) Uani 1 1 d . . .
C16 C 0.95730(19) 0.3716(2) 0.1293(5) 0.0602(9) Uani 1 1 d . . .
C17 C 0.65532(19) 0.5692(2) 0.1297(5) 0.0675(10) Uani 1 1 d . . .
H17 H 0.6853 0.5232 0.1529 0.081 Uiso 1 1 calc R . .
C18 C 1.36398(18) 0.6082(2) 0.5641(5) 0.0635(10) Uani 1 1 d . . .
C19 C 0.64239(19) 0.7116(2) 0.0530(4) 0.0644(10) Uani 1 1 d . . .
C20 C 1.3959(2) 0.6581(3) 0.7028(6) 0.0813(12) Uani 1 1 d . . .
H20 H 1.4487 0.6637 0.7247 0.098 Uiso 1 1 calc R . .
C21 C 0.7523(2) 0.7904(2) 0.0002(5) 0.0714(11) Uani 1 1 d . . .
H21 H 0.7735 0.8392 -0.0292 0.086 Uiso 1 1 calc R . .
C22 C 0.57848(19) 0.5653(3) 0.1403(5) 0.0770(12) Uani 1 1 d . . .
H22 H 0.5568 0.5168 0.1701 0.092 Uiso 1 1 calc R . .
C23 C 0.6762(2) 0.7857(2) 0.0114(5) 0.0741(11) Uani 1 1 d . . .
H23 H 0.6460 0.8317 -0.0085 0.089 Uiso 1 1 calc R . .
C24 C 1.29772(19) 0.5095(3) 0.2913(5) 0.0828(12) Uani 1 1 d . . .
H24 H 1.2762 0.4769 0.1981 0.099 Uiso 1 1 calc R . .
C25 C 1.2389(2) 0.6424(2) 0.6422(5) 0.0738(11) Uani 1 1 d . . .
H25 H 1.1860 0.6376 0.6246 0.089 Uiso 1 1 calc R . .
C26 C 1.3517(3) 0.6985(3) 0.8060(6) 0.0995(15) Uani 1 1 d . . .
H26 H 1.3739 0.7310 0.8987 0.119 Uiso 1 1 calc R . .
C27 C 0.9307(2) 0.2908(2) 0.0528(6) 0.0848(12) Uani 1 1 d . . .
H27A H 0.9137 0.2580 0.1441 0.127 Uiso 1 1 calc R . .
H27B H 0.9722 0.2642 0.0066 0.127 Uiso 1 1 calc R . .
H27C H 0.8894 0.2988 -0.0410 0.127 Uiso 1 1 calc R . .
C28 C 1.2726(2) 0.6909(3) 0.7718(6) 0.0970(14) Uani 1 1 d . . .
H28 H 1.2422 0.7201 0.8402 0.116 Uiso 1 1 calc R . .
C29 C 0.5328(2) 0.6334(3) 0.1068(6) 0.0885(14) Uani 1 1 d . . .
H29 H 0.4808 0.6302 0.1137 0.106 Uiso 1 1 calc R . .
C30 C 0.5639(2) 0.7047(3) 0.0640(5) 0.0800(12) Uani 1 1 d . . .
H30 H 0.5327 0.7499 0.0415 0.096 Uiso 1 1 calc R . .
C31 C 1.3774(2) 0.5191(3) 0.3222(6) 0.0928(14) Uani 1 1 d . . .
H31 H 1.4081 0.4926 0.2502 0.111 Uiso 1 1 calc R . .
C32 C 1.4097(2) 0.5669(3) 0.4563(5) 0.0809(12) Uani 1 1 d . . .
H32 H 1.4625 0.5724 0.4769 0.097 Uiso 1 1 calc R . .


_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
O1 C3 1.352(4) . ?
N3 C33 1.276(4) . ?
N3 C15 1.427(4) . ?
C3 C6 1.396(4) . ?
C3 C5 1.400(4) . ?
N4 C34 1.279(4) . ?
N4 C12 1.421(4) . ?
C5 C9 1.385(5) . ?
C5 C33 1.449(4) . ?
C6 C7 1.382(4) . ?
C6 C34 1.462(4) . ?
C7 C16 1.384(4) . ?
C8 C17 1.411(5) . ?
C8 C19 1.419(4) . ?
C8 C12 1.421(4) . ?
C9 C16 1.391(4) . ?
C10 C15 1.402(4) . ?
C10 C25 1.414(5) . ?
C10 C18 1.423(4) . ?
C12 C14 1.370(5) . ?
C14 C21 1.393(5) . ?
C15 C24 1.361(5) . ?
C16 C27 1.507(5) . ?
C17 C22 1.372(5) . ?
C18 C20 1.397(5) . ?
C18 C32 1.401(5) . ?
C19 C30 1.404(5) . ?
C19 C23 1.416(5) . ?
C20 C26 1.354(5) . ?
C21 C23 1.360(5) . ?
C22 C29 1.388(5) . ?
C24 C31 1.405(5) . ?
C25 C28 1.345(5) . ?
C26 C28 1.393(5) . ?
C29 C30 1.358(6) . ?
C31 C32 1.354(5) . ?

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
C33 N3 C15 118.8(3) . . ?
O1 C3 C6 118.8(3) . . ?
O1 C3 C5 121.3(3) . . ?
C6 C3 C5 119.9(3) . . ?
C34 N4 C12 118.5(3) . . ?
C9 C5 C3 118.8(3) . . ?
C9 C5 C33 120.3(3) . . ?
C3 C5 C33 120.6(3) . . ?
C7 C6 C3 118.9(3) . . ?
C7 C6 C34 121.3(3) . . ?
C3 C6 C34 119.6(3) . . ?
C6 C7 C16 122.9(3) . . ?
C17 C8 C19 118.2(3) . . ?
C17 C8 C12 122.8(3) . . ?
C19 C8 C12 119.0(3) . . ?
C5 C9 C16 122.6(3) . . ?
C15 C10 C25 123.4(3) . . ?
C15 C10 C18 118.9(3) . . ?
C25 C10 C18 117.7(3) . . ?
N3 C33 C5 123.4(3) . . ?
C14 C12 N4 123.2(3) . . ?
C14 C12 C8 119.8(3) . . ?
N4 C12 C8 116.9(3) . . ?
N4 C34 C6 121.7(3) . . ?
C12 C14 C21 121.2(3) . . ?
C24 C15 C10 120.1(3) . . ?
C24 C15 N3 122.4(3) . . ?
C10 C15 N3 117.5(3) . . ?
C7 C16 C9 116.8(3) . . ?
C7 C16 C27 122.2(3) . . ?
C9 C16 C27 120.9(3) . . ?
C22 C17 C8 120.8(3) . . ?
C20 C18 C32 121.5(3) . . ?
C20 C18 C10 119.2(3) . . ?
C32 C18 C10 119.3(3) . . ?
C30 C19 C23 122.1(4) . . ?
C30 C19 C8 119.1(4) . . ?
C23 C19 C8 118.8(3) . . ?
C26 C20 C18 121.5(4) . . ?
C23 C21 C14 120.4(4) . . ?
C17 C22 C29 120.4(4) . . ?
C21 C23 C19 120.8(3) . . ?
C15 C24 C31 120.9(4) . . ?
C28 C25 C10 120.7(4) . . ?
C20 C26 C28 119.2(4) . . ?
C25 C28 C26 121.7(4) . . ?
C30 C29 C22 120.3(4) . . ?
C29 C30 C19 121.2(4) . . ?
C32 C31 C24 120.3(4) . . ?
C31 C32 C18 120.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.133
