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

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_exp_3068
_database_code_depnum_ccdc_archive 'CCDC 1000768'
_audit_update_record             
;
2014-05-04 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 Mg N3 O5'
_chemical_formula_weight         400.65

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'
Mg Mg 0.0486 0.0363 '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           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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                   16.0685(17)
_cell_length_b                   14.6258(12)
_cell_length_c                   9.3457(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.798(8)
_cell_angle_gamma                90.00
_cell_volume                     1942.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    1475
_cell_measurement_theta_min      2.7910
_cell_measurement_theta_max      27.7050

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             828
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81428
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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            5284
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         25.01
_reflns_number_total             1716
_reflns_number_gt                1381
_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)+(0.1214P)²+4.3350P] 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         1716
_refine_ls_number_parameters     144
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.2148
_refine_ls_wR_factor_gt          0.1958
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.131
_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
Mg1 Mg 0.5000 0.95728(9) -0.2500 0.0305(5) Uani 1 2 d SU . .
O1 O 0.60729(18) 0.94682(18) -0.0193(3) 0.0467(7) Uani 1 1 d U . .
O2 O 0.60016(17) 1.03281(17) 0.1710(3) 0.0408(7) Uani 1 1 d U . .
N2 N 1.0000 0.8062(3) 0.7500 0.0338(9) Uani 1 2 d SU . .
N3 N 1.0000 0.6158(2) 0.7500 0.0328(9) Uani 1 2 d SU . .
O5 O 0.5000 0.8170(3) -0.2500 0.0725(13) Uani 1 2 d SU . .
N1 N 0.5000 0.6653(4) -0.2500 0.0839(18) Uani 1 2 d SU . .
C1 C 0.6341(2) 0.9689(2) 0.1242(4) 0.0348(8) Uani 1 1 d U . .
C2 C 0.7156(2) 0.9156(2) 0.2519(4) 0.0349(8) Uani 1 1 d U . .
C3 C 0.7417(2) 0.8315(3) 0.2155(4) 0.0391(8) Uani 1 1 d U . .
H3 H 0.7118 0.8099 0.1098 0.047 Uiso 1 1 calc R . .
C4 C 0.8120(2) 0.7796(2) 0.3356(4) 0.0388(8) Uani 1 1 d U . .
H4 H 0.8281 0.7230 0.3101 0.047 Uiso 1 1 calc R . .
C5 C 0.8586(2) 0.8119(2) 0.4944(4) 0.0328(8) Uani 1 1 d U . .
C6 C 0.8327(3) 0.8967(2) 0.5289(4) 0.0391(8) Uani 1 1 d U . .
H6 H 0.8639 0.9196 0.6337 0.047 Uiso 1 1 calc R . .
C7 C 0.7615(3) 0.9474(2) 0.4097(4) 0.0397(8) Uani 1 1 d U . .
H7 H 0.7442 1.0033 0.4356 0.048 Uiso 1 1 calc R . .
C8 C 0.9341(2) 0.7587(2) 0.6271(4) 0.0317(8) Uani 1 1 d U . .
C9 C 0.9359(2) 0.6637(2) 0.6264(4) 0.0346(8) Uani 1 1 d U . .
H9 H 0.8909 0.6326 0.5369 0.042 Uiso 1 1 calc R . .
C10 C 0.5144(6) 0.7565(6) -0.1854(11) 0.0519(17) Uani 0.50 1 d PU . .
H10 H 0.5361 0.7253 -0.0878 0.062 Uiso 0.50 1 calc PR . .
C11 C 0.4549(8) 0.6209(9) -0.3986(15) 0.095(3) Uani 0.50 1 d PU . .
H11A H 0.4991 0.5827 -0.4126 0.143 Uiso 0.50 1 calc PR . .
H11B H 0.4297 0.6654 -0.4839 0.143 Uiso 0.50 1 calc PR . .
H11C H 0.4046 0.5839 -0.4018 0.143 Uiso 0.50 1 calc PR . .


_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
Mg1 O1 2.044(2) 2_654 ?
Mg1 O1 2.044(2) . ?
Mg1 O5 2.052(5) . ?
Mg1 O2 2.065(2) 6_575 ?
Mg1 O2 2.065(2) 5_675 ?
Mg1 N3 2.318(4) 3_454 ?
O1 C1 1.245(4) . ?
O2 C1 1.258(4) . ?
O2 Mg1 2.065(2) 5_675 ?
N2 C8 1.337(4) . ?
N2 C8 1.337(4) 2_756 ?
N3 C9 1.334(4) 2_756 ?
N3 C9 1.334(4) . ?
N3 Mg1 2.318(4) 3_546 ?
O5 C10 1.034(8) 2_654 ?
O5 C10 1.034(8) . ?
N1 C11 1.392(12) . ?
N1 C11 1.392(12) 2_654 ?
N1 C10 1.437(10) . ?
N1 C10 1.437(10) 2_654 ?
C1 C2 1.514(4) . ?
C2 C7 1.385(5) . ?
C2 C3 1.392(5) . ?
C3 C4 1.389(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(5) . ?
C5 C8 1.488(4) . ?
C6 C7 1.383(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.390(5) . ?
C9 H9 0.9300 . ?
C10 C10 1.073(17) 2_654 ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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 Mg1 O1 171.41(17) 2_654 . ?
O1 Mg1 O5 85.71(8) 2_654 . ?
O1 Mg1 O5 85.71(8) . . ?
O1 Mg1 O2 92.45(10) 2_654 6_575 ?
O1 Mg1 O2 88.16(10) . 6_575 ?
O5 Mg1 O2 94.03(8) . 6_575 ?
O1 Mg1 O2 88.16(10) 2_654 5_675 ?
O1 Mg1 O2 92.45(10) . 5_675 ?
O5 Mg1 O2 94.03(8) . 5_675 ?
O2 Mg1 O2 171.95(16) 6_575 5_675 ?
O1 Mg1 N3 94.29(8) 2_654 3_454 ?
O1 Mg1 N3 94.29(8) . 3_454 ?
O5 Mg1 N3 180.000(1) . 3_454 ?
O2 Mg1 N3 85.97(8) 6_575 3_454 ?
O2 Mg1 N3 85.97(8) 5_675 3_454 ?
C1 O1 Mg1 144.6(2) . . ?
C1 O2 Mg1 135.4(2) . 5_675 ?
C8 N2 C8 117.4(4) . 2_756 ?
C9 N3 C9 116.5(4) 2_756 . ?
C9 N3 Mg1 121.74(19) 2_756 3_546 ?
C9 N3 Mg1 121.74(19) . 3_546 ?
C10 O5 C10 62.5(10) 2_654 . ?
C10 O5 Mg1 148.8(5) 2_654 . ?
C10 O5 Mg1 148.8(5) . . ?
C11 N1 C11 124.3(11) . 2_654 ?
C11 N1 C10 139.4(7) . . ?
C11 N1 C10 96.2(7) 2_654 . ?
C11 N1 C10 96.2(7) . 2_654 ?
C11 N1 C10 139.4(7) 2_654 2_654 ?
C10 N1 C10 43.8(7) . 2_654 ?
O1 C1 O2 125.4(3) . . ?
O1 C1 C2 116.9(3) . . ?
O2 C1 C2 117.7(3) . . ?
C7 C2 C3 119.0(3) . . ?
C7 C2 C1 120.1(3) . . ?
C3 C2 C1 120.7(3) . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 118.6(3) . . ?
C6 C5 C8 119.2(3) . . ?
C4 C5 C8 122.2(3) . . ?
C7 C6 C5 121.0(3) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C2 120.5(3) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
N2 C8 C9 121.0(3) . . ?
N2 C8 C5 117.1(3) . . ?
C9 C8 C5 121.9(3) . . ?
N3 C9 C8 122.0(3) . . ?
N3 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
O5 C10 C10 58.8(5) . 2_654 ?
O5 C10 N1 126.9(8) . . ?
C10 C10 N1 68.1(4) 2_654 . ?
O5 C10 H10 150.6 . . ?
C10 C10 H10 150.6 2_654 . ?
N1 C10 H10 82.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
O1 Mg1 O1 C1 -123.7(4) 2_654 . . . ?
O5 Mg1 O1 C1 -123.7(4) . . . . ?
O2 Mg1 O1 C1 142.1(4) 6_575 . . . ?
O2 Mg1 O1 C1 -29.8(5) 5_675 . . . ?
N3 Mg1 O1 C1 56.3(4) 3_454 . . . ?
O1 Mg1 O5 C10 26.0(9) 2_654 . . 2_654 ?
O1 Mg1 O5 C10 -154.0(9) . . . 2_654 ?
O2 Mg1 O5 C10 -66.1(9) 6_575 . . 2_654 ?
O2 Mg1 O5 C10 113.9(9) 5_675 . . 2_654 ?
N3 Mg1 O5 C10 0(100) 3_454 . . 2_654 ?
O1 Mg1 O5 C10 -154.0(9) 2_654 . . . ?
O1 Mg1 O5 C10 26.0(9) . . . . ?
O2 Mg1 O5 C10 113.9(9) 6_575 . . . ?
O2 Mg1 O5 C10 -66.1(9) 5_675 . . . ?
N3 Mg1 O5 C10 0(100) 3_454 . . . ?
Mg1 O1 C1 O2 -18.0(7) . . . . ?
Mg1 O1 C1 C2 163.5(3) . . . . ?
Mg1 O2 C1 O1 95.5(4) 5_675 . . . ?
Mg1 O2 C1 C2 -85.9(4) 5_675 . . . ?
O1 C1 C2 C7 167.0(3) . . . . ?
O2 C1 C2 C7 -11.7(5) . . . . ?
O1 C1 C2 C3 -17.2(5) . . . . ?
O2 C1 C2 C3 164.1(3) . . . . ?
C7 C2 C3 C4 0.6(5) . . . . ?
C1 C2 C3 C4 -175.2(3) . . . . ?
C2 C3 C4 C5 -1.0(6) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C3 C4 C5 C8 179.9(3) . . . . ?
C4 C5 C6 C7 1.1(5) . . . . ?
C8 C5 C6 C7 -178.6(3) . . . . ?
C5 C6 C7 C2 -1.5(6) . . . . ?
C3 C2 C7 C6 0.6(6) . . . . ?
C1 C2 C7 C6 176.5(3) . . . . ?
C8 N2 C8 C9 -1.4(2) 2_756 . . . ?
C8 N2 C8 C5 177.3(3) 2_756 . . . ?
C6 C5 C8 N2 -28.6(4) . . . . ?
C4 C5 C8 N2 151.7(3) . . . . ?
C6 C5 C8 C9 150.1(3) . . . . ?
C4 C5 C8 C9 -29.6(5) . . . . ?
C9 N3 C9 C8 -1.5(2) 2_756 . . . ?
Mg1 N3 C9 C8 178.5(2) 3_546 . . . ?
N2 C8 C9 N3 3.0(5) . . . . ?
C5 C8 C9 N3 -175.6(3) . . . . ?
Mg1 O5 C10 C10 180.000(5) . . . 2_654 ?
C10 O5 C10 N1 0.000(2) 2_654 . . . ?
Mg1 O5 C10 N1 180.000(2) . . . . ?
C11 N1 C10 O5 -12.3(14) . . . . ?
C11 N1 C10 O5 172.0(9) 2_654 . . . ?
C10 N1 C10 O5 0.000(1) 2_654 . . . ?
C11 N1 C10 C10 -12.3(14) . . . 2_654 ?
C11 N1 C10 C10 172.0(9) 2_654 . . 2_654 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.081
