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


data_ye69sadpbca

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 N3 O2'
_chemical_formula_weight         335.40

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   12.835(3)
_cell_length_b                   9.3810(19)
_cell_length_c                   28.713(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3457.2(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    3406
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.5

_exptl_crystal_description       needle
_exptl_crystal_colour            dark
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1424
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9832
_exptl_absorpt_correction_T_max  0.9992
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      170(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18350
_diffrn_reflns_av_R_equivalents  0.1756
_diffrn_reflns_av_unetI/netI     0.1617
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3394
_reflns_number_gt                2245
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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 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)+(0.0749P)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       0.0146(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3394
_refine_ls_number_parameters     231
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1587
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.1596
_refine_ls_wR_factor_gt          0.1328
_refine_ls_goodness_of_fit_ref   0.769
_refine_ls_restrained_S_all      0.770
_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
C1 C 0.3126(3) 0.1612(3) 0.27232(11) 0.0378(8) Uani 1 1 d . . .
C2 C 0.3014(3) 0.0541(4) 0.23956(11) 0.0514(10) Uani 1 1 d . . .
H2 H 0.2461 -0.0126 0.2425 0.062 Uiso 1 1 calc R . .
C3 C 0.3698(3) 0.0430(4) 0.20258(12) 0.0593(11) Uani 1 1 d . . .
H3 H 0.3615 -0.0321 0.1807 0.071 Uiso 1 1 calc R . .
C4 C 0.4490(3) 0.1383(5) 0.19703(13) 0.0584(11) Uani 1 1 d . . .
H4 H 0.4951 0.1304 0.1713 0.070 Uiso 1 1 calc R . .
C5 C 0.4619(3) 0.2467(4) 0.22920(13) 0.0537(10) Uani 1 1 d . . .
H5 H 0.5173 0.3131 0.2257 0.064 Uiso 1 1 calc R . .
C6 C 0.3937(3) 0.2586(4) 0.26670(11) 0.0448(9) Uani 1 1 d . . .
H6 H 0.4025 0.3336 0.2886 0.054 Uiso 1 1 calc R . .
C7 C 0.2419(3) 0.1596(4) 0.31353(11) 0.0382(8) Uani 1 1 d . . .
C8 C 0.2067(2) 0.3809(4) 0.40991(11) 0.0388(9) Uani 1 1 d . . .
H8 H 0.2517 0.4545 0.3994 0.047 Uiso 1 1 calc R . .
C9 C 0.1621(2) 0.3916(3) 0.45553(11) 0.0369(8) Uani 1 1 d . . .
C10 C 0.0974(2) 0.2862(3) 0.47489(12) 0.0386(9) Uani 1 1 d . . .
C11 C 0.0607(3) 0.2935(3) 0.52035(12) 0.0400(9) Uani 1 1 d . . .
C12 C -0.0045(3) 0.1744(4) 0.53947(9) 0.0526(10) Uani 1 1 d D . .
H12A H 0.0204 0.0825 0.5266 0.063 Uiso 1 1 calc R . .
H12B H -0.0778 0.1875 0.5296 0.063 Uiso 1 1 calc R . .
C13 C 0.0009(3) 0.1697(4) 0.59298(9) 0.0564(11) Uani 1 1 d D . .
H13A H -0.0533 0.1045 0.6051 0.068 Uiso 1 1 calc R . .
H13B H 0.0698 0.1333 0.6029 0.068 Uiso 1 1 calc R . .
C14 C -0.0157(3) 0.3167(4) 0.61237(12) 0.0550(11) Uani 1 1 d . . .
H14A H -0.0865 0.3500 0.6041 0.066 Uiso 1 1 calc R . .
H14B H -0.0108 0.3133 0.6468 0.066 Uiso 1 1 calc R . .
C15 C 0.0824(3) 0.5408(4) 0.62317(12) 0.0548(10) Uani 1 1 d . . .
H15A H 0.0854 0.5115 0.6563 0.066 Uiso 1 1 calc R . .
H15B H 0.0251 0.6107 0.6197 0.066 Uiso 1 1 calc R . .
C16 C 0.1836(3) 0.6096(4) 0.60980(10) 0.0614(11) Uani 1 1 d D . .
H16A H 0.2418 0.5427 0.6155 0.074 Uiso 1 1 calc R . .
H16B H 0.1951 0.6959 0.6290 0.074 Uiso 1 1 calc R . .
C17 C 0.1802(3) 0.6505(4) 0.55799(9) 0.0520(10) Uani 1 1 d D . .
H17A H 0.1274 0.7259 0.5530 0.062 Uiso 1 1 calc R . .
H17B H 0.2489 0.6883 0.5483 0.062 Uiso 1 1 calc R . .
C18 C 0.1534(2) 0.5219(3) 0.52928(12) 0.0403(9) Uani 1 1 d . . .
C19 C 0.1886(3) 0.5071(3) 0.48423(11) 0.0430(9) Uani 1 1 d . . .
H19 H 0.2331 0.5788 0.4720 0.052 Uiso 1 1 calc R . .
C20 C 0.0907(2) 0.4112(4) 0.54807(11) 0.0396(9) Uani 1 1 d . . .
N1 N 0.2401(2) 0.2774(3) 0.34005(9) 0.0412(8) Uani 1 1 d . . .
H1N H 0.274(2) 0.362(4) 0.3319(11) 0.062 Uiso 1 1 d . . .
N2 N 0.1876(2) 0.2742(3) 0.38259(9) 0.0400(7) Uani 1 1 d . . .
N3 N 0.0610(2) 0.4169(3) 0.59437(9) 0.0476(8) Uani 1 1 d . . .
O1 O 0.19021(17) 0.0525(2) 0.32391(7) 0.0454(6) Uani 1 1 d . . .
O2 O 0.06790(18) 0.1708(2) 0.44898(7) 0.0479(7) Uani 1 1 d . . .
H2A H 0.0948 0.1762 0.4224 0.072 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
C1 C2 1.384(4) . ?
C1 C6 1.394(4) . ?
C1 C7 1.492(4) . ?
C2 C3 1.382(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.364(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.240(3) . ?
C7 N1 1.342(4) . ?
C8 N2 1.295(4) . ?
C8 C9 1.433(4) . ?
C8 H8 0.9500 . ?
C9 C19 1.403(4) . ?
C9 C10 1.405(4) . ?
C10 O2 1.368(3) . ?
C10 C11 1.390(4) . ?
C11 C20 1.414(4) . ?
C11 C12 1.500(4) . ?
C12 C13 1.5388(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.502(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N3 1.456(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 N3 1.453(4) . ?
C15 C16 1.500(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5368(19) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.501(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.377(4) . ?
C18 C20 1.421(4) . ?
C19 H19 0.9500 . ?
C20 N3 1.384(4) . ?
N1 N2 1.395(3) . ?
N1 H1N 0.94(3) . ?
O2 H2A 0.8400 . ?

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 C1 C6 118.4(3) . . ?
C2 C1 C7 117.9(3) . . ?
C6 C1 C7 123.6(3) . . ?
C3 C2 C1 120.7(4) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 121.0(4) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 120.0(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O1 C7 N1 121.4(3) . . ?
O1 C7 C1 121.6(3) . . ?
N1 C7 C1 116.9(3) . . ?
N2 C8 C9 122.2(3) . . ?
N2 C8 H8 118.9 . . ?
C9 C8 H8 118.9 . . ?
C19 C9 C10 117.0(3) . . ?
C19 C9 C8 119.6(3) . . ?
C10 C9 C8 123.2(3) . . ?
O2 C10 C11 117.1(3) . . ?
O2 C10 C9 120.4(3) . . ?
C11 C10 C9 122.5(3) . . ?
C10 C11 C20 118.3(3) . . ?
C10 C11 C12 119.7(3) . . ?
C20 C11 C12 121.9(3) . . ?
C11 C12 C13 111.2(3) . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 109.8(3) . . ?
C14 C13 H13A 109.7 . . ?
C12 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
C12 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
N3 C14 C13 111.4(3) . . ?
N3 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
N3 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
N3 C15 C16 111.3(3) . . ?
N3 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
N3 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 C17 109.3(3) . . ?
C15 C16 H16A 109.8 . . ?
C17 C16 H16A 109.8 . . ?
C15 C16 H16B 109.8 . . ?
C17 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
C18 C17 C16 109.7(3) . . ?
C18 C17 H17A 109.7 . . ?
C16 C17 H17A 109.7 . . ?
C18 C17 H17B 109.7 . . ?
C16 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C19 C18 C20 118.0(3) . . ?
C19 C18 C17 121.4(3) . . ?
C20 C18 C17 120.6(3) . . ?
C18 C19 C9 123.3(3) . . ?
C18 C19 H19 118.3 . . ?
C9 C19 H19 118.3 . . ?
N3 C20 C11 119.7(3) . . ?
N3 C20 C18 119.5(3) . . ?
C11 C20 C18 120.8(3) . . ?
C7 N1 N2 119.2(3) . . ?
C7 N1 H1N 123(2) . . ?
N2 N1 H1N 118(2) . . ?
C8 N2 N1 115.0(3) . . ?
C20 N3 C15 121.7(3) . . ?
C20 N3 C14 120.1(3) . . ?
C15 N3 C14 116.3(3) . . ?
C10 O2 H2A 109.5 . . ?

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 C1 C2 C3 0.8(5) . . . . ?
C7 C1 C2 C3 -174.8(3) . . . . ?
C1 C2 C3 C4 -0.9(6) . . . . ?
C2 C3 C4 C5 0.7(6) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C4 C5 C6 C1 0.4(5) . . . . ?
C2 C1 C6 C5 -0.6(5) . . . . ?
C7 C1 C6 C5 174.8(3) . . . . ?
C2 C1 C7 O1 15.1(5) . . . . ?
C6 C1 C7 O1 -160.3(3) . . . . ?
C2 C1 C7 N1 -167.7(3) . . . . ?
C6 C1 C7 N1 16.9(5) . . . . ?
N2 C8 C9 C19 177.7(3) . . . . ?
N2 C8 C9 C10 2.2(5) . . . . ?
C19 C9 C10 O2 179.7(3) . . . . ?
C8 C9 C10 O2 -4.7(5) . . . . ?
C19 C9 C10 C11 -0.2(5) . . . . ?
C8 C9 C10 C11 175.4(3) . . . . ?
O2 C10 C11 C20 179.5(3) . . . . ?
C9 C10 C11 C20 -0.6(5) . . . . ?
O2 C10 C11 C12 2.6(4) . . . . ?
C9 C10 C11 C12 -177.5(3) . . . . ?
C10 C11 C12 C13 156.4(3) . . . . ?
C20 C11 C12 C13 -20.3(4) . . . . ?
C11 C12 C13 C14 47.6(4) . . . . ?
C12 C13 C14 N3 -57.9(4) . . . . ?
N3 C15 C16 C17 57.2(4) . . . . ?
C15 C16 C17 C18 -54.5(4) . . . . ?
C16 C17 C18 C19 -150.5(3) . . . . ?
C16 C17 C18 C20 29.4(4) . . . . ?
C20 C18 C19 C9 2.7(5) . . . . ?
C17 C18 C19 C9 -177.4(3) . . . . ?
C10 C9 C19 C18 -0.9(5) . . . . ?
C8 C9 C19 C18 -176.7(3) . . . . ?
C10 C11 C20 N3 -175.8(3) . . . . ?
C12 C11 C20 N3 1.0(5) . . . . ?
C10 C11 C20 C18 2.5(5) . . . . ?
C12 C11 C20 C18 179.3(3) . . . . ?
C19 C18 C20 N3 174.8(3) . . . . ?
C17 C18 C20 N3 -5.1(5) . . . . ?
C19 C18 C20 C11 -3.5(5) . . . . ?
C17 C18 C20 C11 176.6(3) . . . . ?
O1 C7 N1 N2 6.6(5) . . . . ?
C1 C7 N1 N2 -170.6(3) . . . . ?
C9 C8 N2 N1 -177.7(3) . . . . ?
C7 N1 N2 C8 166.9(3) . . . . ?
C11 C20 N3 C15 -174.8(3) . . . . ?
C18 C20 N3 C15 6.9(5) . . . . ?
C11 C20 N3 C14 -11.0(4) . . . . ?
C18 C20 N3 C14 170.7(3) . . . . ?
C16 C15 N3 C20 -33.9(4) . . . . ?
C16 C15 N3 C14 161.7(3) . . . . ?
C13 C14 N3 C20 40.3(4) . . . . ?
C13 C14 N3 C15 -155.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.061

# start Validation Reply Form
_vrf_PLAT020_ye69sapbca          
;
PROBLEM: Large R(int) ................................. 0.18
RESPONSE: Data were not of the highest quality.  
;
# end Validation Reply Form
_database_code_depnum_ccdc_archive 'CCDC 972999'
