# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1475610'
_audit_update_record             
;
2016-04-21 deposited with the CCDC.
2016-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H26 N4 O2'
_chemical_formula_weight         378.47

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   block

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

_cell_length_a                   7.8442(7)
_cell_length_b                   23.492(2)
_cell_length_c                   10.7644(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.014(3)
_cell_angle_gamma                90.00
_cell_volume                     1964.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            origin
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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            14222
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4434
_reflns_number_gt                2491
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.1265P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4434
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1136
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.2271
_refine_ls_wR_factor_gt          0.1938
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.8737(4) 0.57730(12) 0.3297(3) 0.0727(9) Uani 1 1 d . . .
H1 H 0.9177 0.6123 0.3089 0.087 Uiso 1 1 calc R . .
C2 C 0.8593(4) 0.53496(12) 0.2396(3) 0.0738(9) Uani 1 1 d . . .
H2 H 0.8915 0.5416 0.1609 0.089 Uiso 1 1 calc R . .
C3 C 0.7968(4) 0.48334(11) 0.2691(3) 0.0602(7) Uani 1 1 d . . .
H3 H 0.7835 0.4544 0.2096 0.072 Uiso 1 1 calc R . .
C4 C 0.7527(3) 0.47403(10) 0.3883(2) 0.0504(6) Uani 1 1 d . . .
C5 C 0.7693(3) 0.52029(10) 0.4742(2) 0.0494(6) Uani 1 1 d . . .
C6 C 0.6901(3) 0.42046(10) 0.4272(3) 0.0528(6) Uani 1 1 d . . .
H6 H 0.6752 0.3906 0.3700 0.063 Uiso 1 1 calc R . .
C7 C 0.6521(3) 0.41205(9) 0.5448(2) 0.0445(6) Uani 1 1 d . . .
C8 C 0.6699(3) 0.45757(10) 0.6351(2) 0.0498(6) Uani 1 1 d . . .
C9 C 0.6333(3) 0.45197(12) 0.7580(3) 0.0581(7) Uani 1 1 d . . .
H9 H 0.6038 0.4165 0.7869 0.070 Uiso 1 1 calc R . .
C10 C 0.6402(4) 0.49787(12) 0.8361(3) 0.0668(8) Uani 1 1 d . . .
H10 H 0.6173 0.4944 0.9183 0.080 Uiso 1 1 calc R . .
C11 C 0.6836(4) 0.55090(13) 0.7872(3) 0.0739(8) Uani 1 1 d . . .
H11 H 0.6844 0.5825 0.8394 0.089 Uiso 1 1 calc R . .
C12 C 0.7207(3) 0.51292(9) 0.5973(3) 0.0489(6) Uani 1 1 d . . .
C13 C 0.5933(3) 0.35425(10) 0.5812(2) 0.0496(6) Uani 1 1 d . . .
C14 C 0.3704(3) 0.28127(9) 0.5490(2) 0.0445(5) Uani 1 1 d . . .
H14 H 0.3769 0.2798 0.6406 0.053 Uiso 1 1 calc R . .
C15 C 0.4658(3) 0.23055(9) 0.5075(2) 0.0486(6) Uani 1 1 d . . .
H15A H 0.5874 0.2348 0.5379 0.058 Uiso 1 1 calc R . .
H15B H 0.4525 0.2299 0.4166 0.058 Uiso 1 1 calc R . .
C16 C 0.4034(3) 0.17407(9) 0.5542(2) 0.0431(5) Uani 1 1 d . . .
C17 C 0.0958(3) 0.22312(10) 0.5376(2) 0.0443(6) Uani 1 1 d . . .
C18 C 0.1837(3) 0.27696(10) 0.4929(2) 0.0494(6) Uani 1 1 d . . .
H18A H 0.1757 0.2762 0.4022 0.059 Uiso 1 1 calc R . .
H18B H 0.1229 0.3105 0.5159 0.059 Uiso 1 1 calc R . .
C19 C -0.0659(3) 0.21027(13) 0.4444(3) 0.0641(7) Uani 1 1 d . . .
H19A H -0.0330 0.1994 0.3651 0.096 Uiso 1 1 calc R . .
H19B H -0.1372 0.2436 0.4336 0.096 Uiso 1 1 calc R . .
H19C H -0.1287 0.1797 0.4762 0.096 Uiso 1 1 calc R . .
C20 C 0.0457(4) 0.23141(12) 0.6682(3) 0.0650(8) Uani 1 1 d . . .
H20A H 0.0018 0.1963 0.6965 0.097 Uiso 1 1 calc R . .
H20B H -0.0412 0.2603 0.6653 0.097 Uiso 1 1 calc R . .
H20C H 0.1451 0.2428 0.7251 0.097 Uiso 1 1 calc R . .
C21 C 0.4615(4) 0.12545(11) 0.4756(3) 0.0623(7) Uani 1 1 d . . .
H21A H 0.4281 0.0897 0.5082 0.093 Uiso 1 1 calc R . .
H21B H 0.5844 0.1266 0.4791 0.093 Uiso 1 1 calc R . .
H21C H 0.4085 0.1295 0.3901 0.093 Uiso 1 1 calc R . .
C22 C 0.4718(4) 0.16532(11) 0.6925(3) 0.0620(7) Uani 1 1 d . . .
H22A H 0.4317 0.1956 0.7410 0.093 Uiso 1 1 calc R . .
H22B H 0.5954 0.1654 0.7036 0.093 Uiso 1 1 calc R . .
H22C H 0.4314 0.1295 0.7201 0.093 Uiso 1 1 calc R . .
N1 N 0.8294(3) 0.57172(9) 0.4437(2) 0.0601(6) Uani 1 1 d . . .
N2 N 0.7228(3) 0.55927(9) 0.6741(2) 0.0592(6) Uani 1 1 d . . .
N3 N 0.4465(2) 0.33530(7) 0.51568(19) 0.0465(5) Uani 1 1 d . . .
H3A H 0.3964 0.3549 0.4536 0.056 Uiso 1 1 calc R . .
N4 N 0.2104(2) 0.17293(8) 0.53811(19) 0.0471(5) Uani 1 1 d . . .
O1 O 0.6753(3) 0.32714(7) 0.66840(19) 0.0680(6) Uani 1 1 d . . .
O2 O 0.1426(3) 0.12436(8) 0.5574(2) 0.0716(6) Uani 1 1 d . . .
H2A H 0.1439 0.1196 0.6330 0.107 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 N1 1.328(3) . ?
C1 C2 1.383(4) . ?
C2 C3 1.362(4) . ?
C3 C4 1.392(3) . ?
C4 C5 1.421(3) . ?
C4 C6 1.434(3) . ?
C5 N1 1.354(3) . ?
C5 C12 1.439(4) . ?
C6 C7 1.355(3) . ?
C7 C8 1.439(3) . ?
C7 C13 1.503(3) . ?
C8 C9 1.399(3) . ?
C8 C12 1.435(3) . ?
C9 C10 1.363(4) . ?
C10 C11 1.413(4) . ?
C11 N2 1.312(4) . ?
C12 N2 1.366(3) . ?
C13 O1 1.238(3) . ?
C13 N3 1.340(3) . ?
C14 N3 1.468(3) . ?
C14 C15 1.507(3) . ?
C14 C18 1.508(3) . ?
C15 C16 1.524(3) . ?
C16 N4 1.500(3) . ?
C16 C22 1.525(4) . ?
C16 C21 1.528(3) . ?
C17 N4 1.482(3) . ?
C17 C20 1.525(3) . ?
C17 C19 1.533(4) . ?
C17 C18 1.549(3) . ?
N4 O2 1.288(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
N1 C1 C2 124.8(2) . . ?
C3 C2 C1 118.3(3) . . ?
C2 C3 C4 119.9(3) . . ?
C3 C4 C5 117.9(2) . . ?
C3 C4 C6 123.1(2) . . ?
C5 C4 C6 119.0(2) . . ?
N1 C5 C4 121.9(2) . . ?
N1 C5 C12 118.4(2) . . ?
C4 C5 C12 119.7(2) . . ?
C7 C6 C4 122.0(2) . . ?
C6 C7 C8 120.7(2) . . ?
C6 C7 C13 119.4(2) . . ?
C8 C7 C13 120.0(2) . . ?
C9 C8 C12 117.1(2) . . ?
C9 C8 C7 123.8(2) . . ?
C12 C8 C7 119.1(2) . . ?
C10 C9 C8 120.9(3) . . ?
C9 C10 C11 117.3(3) . . ?
N2 C11 C10 125.3(3) . . ?
N2 C12 C8 122.1(2) . . ?
N2 C12 C5 118.6(2) . . ?
C8 C12 C5 119.3(2) . . ?
O1 C13 N3 123.1(2) . . ?
O1 C13 C7 121.1(2) . . ?
N3 C13 C7 115.8(2) . . ?
N3 C14 C15 112.05(18) . . ?
N3 C14 C18 111.41(18) . . ?
C15 C14 C18 108.8(2) . . ?
C14 C15 C16 113.27(18) . . ?
N4 C16 C15 110.06(17) . . ?
N4 C16 C22 108.82(19) . . ?
C15 C16 C22 110.72(19) . . ?
N4 C16 C21 107.28(18) . . ?
C15 C16 C21 109.51(19) . . ?
C22 C16 C21 110.4(2) . . ?
N4 C17 C20 109.38(19) . . ?
N4 C17 C19 107.0(2) . . ?
C20 C17 C19 109.4(2) . . ?
N4 C17 C18 110.78(17) . . ?
C20 C17 C18 111.4(2) . . ?
C19 C17 C18 108.7(2) . . ?
C14 C18 C17 112.34(19) . . ?
C1 N1 C5 117.2(2) . . ?
C11 N2 C12 117.2(2) . . ?
C13 N3 C14 120.48(19) . . ?
O2 N4 C17 116.19(18) . . ?
O2 N4 C16 115.48(18) . . ?
C17 N4 C16 126.03(17) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.063
_chemical_properties_physical    Heat-sensitive
