# 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_ww
_database_code_depnum_ccdc_archive 'CCDC 1441925'
_audit_update_record             
;
2015-12-11 deposited with the CCDC.
2016-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 Mg N2 O10'
_chemical_formula_weight         522.75

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                   10.717(8)
_cell_length_b                   23.114(18)
_cell_length_c                   10.070(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.780(14)
_cell_angle_gamma                90.00
_cell_volume                     2412(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9720
_exptl_absorpt_correction_T_max  0.9747
_exptl_absorpt_process_details   sadabs

_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  bruker-CCD
_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            8662
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         28.28
_reflns_number_total             2980
_reflns_number_gt                2123
_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)+(0.0627P)²+0.7913P] 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         2980
_refine_ls_number_parameters     196
_refine_ls_number_restraints     74
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1300
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.077
_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 0.15786(3) -0.2500 0.0261(2) Uani 1 2 d S . .
O1 O 0.66037(13) 0.29437(6) -0.14821(17) 0.0420(4) Uani 1 1 d . . .
H1WA H 0.6898 0.2684 -0.1866 0.063 Uiso 1 1 calc R . .
O2 O 0.53768(12) 0.22272(5) -0.10334(15) 0.0322(3) Uani 1 1 d . . .
O3 O 0.28116(13) 0.26207(5) 0.22534(17) 0.0389(4) Uani 1 1 d . . .
O4 O 0.18511(12) 0.34815(5) 0.21614(16) 0.0349(4) Uani 1 1 d . . .
O5 O 0.56155(15) 0.09811(6) -0.09361(18) 0.0424(4) Uani 1 1 d D A .
C1 C 0.57446(17) 0.27385(7) -0.0948(2) 0.0277(4) Uani 1 1 d . . .
C2 C 0.51144(16) 0.31618(7) -0.0204(2) 0.0254(4) Uani 1 1 d . . .
C3 C 0.53437(17) 0.37478(7) -0.0295(2) 0.0279(4) Uani 1 1 d . . .
H3A H 0.5937 0.3874 -0.0765 0.033 Uiso 1 1 calc R . .
C4 C 0.46927(16) 0.41508(7) 0.0310(2) 0.0259(4) Uani 1 1 d . . .
C5 C 0.36087(16) 0.33673(7) 0.11449(19) 0.0230(4) Uani 1 1 d . . .
C6 C 0.42568(16) 0.29741(7) 0.0526(2) 0.0249(4) Uani 1 1 d . . .
H6A H 0.4115 0.2580 0.0601 0.030 Uiso 1 1 calc R . .
C7 C 0.38155(16) 0.39562(7) 0.1028(2) 0.0253(4) Uani 1 1 d . . .
H7A H 0.3370 0.4222 0.1428 0.030 Uiso 1 1 calc R . .
C8 C 0.26716(16) 0.31539(7) 0.1915(2) 0.0261(4) Uani 1 1 d . . .
C9 C 0.49003(17) 0.47529(7) 0.0118(2) 0.0305(4) Uani 1 1 d . . .
C10 C 0.5954(2) 0.11166(11) 0.0270(3) 0.0564(7) Uani 1 1 d DU . .
H10A H 0.5835 0.1508 0.0416 0.068 Uiso 0.595(15) 1 calc PR A 1
H10B H 0.5916 0.1499 0.0541 0.068 Uiso 0.405(15) 1 d PR A 2
C11 C 0.6624(9) 0.1087(4) 0.2776(6) 0.080(2) Uani 0.595(15) 1 d PDU A 1
H11A H 0.6251 0.1467 0.2693 0.119 Uiso 0.595(15) 1 calc PR A 1
H11B H 0.7529 0.1112 0.3219 0.119 Uiso 0.595(15) 1 calc PR A 1
H11C H 0.6207 0.0847 0.3313 0.119 Uiso 0.595(15) 1 calc PR A 1
C11A C 0.7105(14) 0.0856(6) 0.2577(10) 0.090(4) Uani 0.405(15) 1 d PDU A 2
H11D H 0.7147 0.1270 0.2653 0.134 Uiso 0.405(15) 1 calc PR A 2
H11E H 0.7963 0.0702 0.2750 0.134 Uiso 0.405(15) 1 calc PR A 2
H11F H 0.6685 0.0703 0.3236 0.134 Uiso 0.405(15) 1 calc PR A 2
C12 C 0.6927(9) 0.0255(3) 0.1271(9) 0.081(3) Uani 0.595(15) 1 d PDU A 1
H12A H 0.6746 0.0153 0.0317 0.121 Uiso 0.595(15) 1 calc PR A 1
H12B H 0.6509 -0.0015 0.1741 0.121 Uiso 0.595(15) 1 calc PR A 1
H12C H 0.7841 0.0244 0.1667 0.121 Uiso 0.595(15) 1 calc PR A 1
C12A C 0.6142(18) 0.0091(3) 0.0890(12) 0.100(4) Uani 0.405(15) 1 d PDU A 2
H12D H 0.5724 0.0046 -0.0067 0.150 Uiso 0.405(15) 1 calc PR A 2
H12E H 0.5599 -0.0061 0.1430 0.150 Uiso 0.405(15) 1 calc PR A 2
H12F H 0.6948 -0.0114 0.1103 0.150 Uiso 0.405(15) 1 calc PR A 2
N1 N 0.6449(11) 0.0833(3) 0.1404(7) 0.0545(18) Uani 0.595(15) 1 d PDU A 1
N1A N 0.6377(17) 0.0695(4) 0.1197(11) 0.056(3) Uani 0.405(15) 1 d PDU A 2


_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 O2 2.0705(18) . ?
Mg1 O2 2.0705(18) 2_654 ?
Mg1 O5 2.0719(19) 2_654 ?
Mg1 O5 2.0719(19) . ?
Mg1 O4 2.1015(19) 7 ?
Mg1 O4 2.1015(19) 8 ?
O1 C1 1.271(2) . ?
O1 H1WA 0.8200 . ?
O2 C1 1.242(2) . ?
O3 C8 1.277(2) . ?
O4 C8 1.233(2) . ?
O4 Mg1 2.1015(19) 7 ?
O5 C10 1.216(3) . ?
C1 C2 1.494(2) . ?
C2 C3 1.384(3) . ?
C2 C6 1.385(3) . ?
C3 C4 1.394(2) . ?
C3 H3A 0.9300 . ?
C4 C7 1.399(3) . ?
C4 C9 1.430(2) . ?
C5 C6 1.385(2) . ?
C5 C7 1.389(2) . ?
C5 C8 1.500(2) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C9 C9 1.197(3) 5_665 ?
C10 N1 1.306(7) . ?
C10 N1A 1.345(10) . ?
C10 H10A 0.9300 . ?
C10 H10B 0.9299 . ?
C11 N1 1.468(7) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C11A N1A 1.457(8) . ?
C11A H11D 0.9600 . ?
C11A H11E 0.9600 . ?
C11A H11F 0.9600 . ?
C12 N1 1.448(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12A N1A 1.438(9) . ?
C12A H12D 0.9600 . ?
C12A H12E 0.9600 . ?
C12A H12F 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
O2 Mg1 O2 87.23(10) . 2_654 ?
O2 Mg1 O5 172.36(6) . 2_654 ?
O2 Mg1 O5 88.52(9) 2_654 2_654 ?
O2 Mg1 O5 88.52(9) . . ?
O2 Mg1 O5 172.36(6) 2_654 . ?
O5 Mg1 O5 96.39(11) 2_654 . ?
O2 Mg1 O4 87.28(6) . 7 ?
O2 Mg1 O4 98.23(6) 2_654 7 ?
O5 Mg1 O4 87.05(6) 2_654 7 ?
O5 Mg1 O4 87.89(7) . 7 ?
O2 Mg1 O4 98.23(6) . 8 ?
O2 Mg1 O4 87.28(6) 2_654 8 ?
O5 Mg1 O4 87.89(7) 2_654 8 ?
O5 Mg1 O4 87.05(6) . 8 ?
O4 Mg1 O4 172.42(8) 7 8 ?
C1 O1 H1WA 109.5 . . ?
C1 O2 Mg1 137.67(13) . . ?
C8 O4 Mg1 138.03(12) . 7 ?
C10 O5 Mg1 122.90(15) . . ?
O2 C1 O1 125.25(17) . . ?
O2 C1 C2 118.82(16) . . ?
O1 C1 C2 115.90(15) . . ?
C3 C2 C6 119.69(16) . . ?
C3 C2 C1 119.79(16) . . ?
C6 C2 C1 120.46(15) . . ?
C2 C3 C4 120.51(16) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C3 C4 C7 119.25(16) . . ?
C3 C4 C9 118.60(16) . . ?
C7 C4 C9 122.08(16) . . ?
C6 C5 C7 119.71(16) . . ?
C6 C5 C8 119.71(15) . . ?
C7 C5 C8 120.56(15) . . ?
C2 C6 C5 120.69(16) . . ?
C2 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C5 C7 C4 120.13(15) . . ?
C5 C7 H7A 119.9 . . ?
C4 C7 H7A 119.9 . . ?
O4 C8 O3 125.45(17) . . ?
O4 C8 C5 120.54(16) . . ?
O3 C8 C5 114.00(15) . . ?
C9 C9 C4 175.7(3) 5_665 . ?
O5 C10 N1 134.0(4) . . ?
O5 C10 N1A 117.9(5) . . ?
N1 C10 N1A 16.3(6) . . ?
O5 C10 H10A 113.0 . . ?
N1 C10 H10A 113.0 . . ?
N1A C10 H10A 129.0 . . ?
O5 C10 H10B 120.9 . . ?
N1 C10 H10B 105.0 . . ?
N1A C10 H10B 121.1 . . ?
H10A C10 H10B 8.3 . . ?
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 . . ?
N1A C11A H11D 109.5 . . ?
N1A C11A H11E 109.5 . . ?
H11D C11A H11E 109.5 . . ?
N1A C11A H11F 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1A C12A H12D 109.5 . . ?
N1A C12A H12E 109.5 . . ?
H12D C12A H12E 109.5 . . ?
N1A C12A H12F 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
C10 N1 C12 117.1(6) . . ?
C10 N1 C11 123.3(6) . . ?
C12 N1 C11 119.5(6) . . ?
C10 N1A C12A 123.0(7) . . ?
C10 N1A C11A 118.7(7) . . ?
C12A N1A C11A 118.3(9) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.052
