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

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#
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#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_121031c_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H27 N2 O7'
_chemical_formula_weight         384.42

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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3882(14)
_cell_length_b                   11.1278(18)
_cell_length_c                   11.3535(18)
_cell_angle_alpha                71.834(2)
_cell_angle_beta                 79.964(2)
_cell_angle_gamma                73.789(2)
_cell_volume                     962.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3388
_cell_measurement_theta_min      1.90
_cell_measurement_theta_max      25.00

_exptl_crystal_description       rhombic
_exptl_crystal_colour            light-yellow
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             410
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9869
_exptl_absorpt_correction_T_max  0.9980
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'

_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  '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            4320
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3243
_reflns_number_gt                1988
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SHELXTL-Plus (Sheldrick, 1990)'
_computing_cell_refinement       'SHELXTL-Plus (Sheldrick, 1990)'
_computing_data_reduction        'SHELXTL-Plus (Sheldrick, 1990)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL V.5.0 (Sheldrick, 1997)'

_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)+(0.1368P)²+0.6907P] 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       0.009(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3243
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1295
_refine_ls_R_factor_gt           0.0874
_refine_ls_wR_factor_ref         0.2914
_refine_ls_wR_factor_gt          0.2333
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.1971(7) -0.1504(5) 0.4574(4) 0.0576(12) Uani 1 1 d . . .
C2 C 0.2148(6) -0.2408(4) 0.5753(4) 0.0565(12) Uani 1 1 d . . .
C3 C 0.2592(6) -0.2072(4) 0.6702(4) 0.0542(12) Uani 1 1 d . . .
H3 H 0.2737 -0.2679 0.7476 0.065 Uiso 1 1 calc R . .
C4 C 0.2822(6) -0.0832(4) 0.6506(4) 0.0520(11) Uani 1 1 d . . .
C5 C 0.2629(7) 0.0063(5) 0.5339(5) 0.0691(15) Uani 1 1 d . . .
H5 H 0.2775 0.0896 0.5202 0.083 Uiso 1 1 calc R . .
C6 C 0.2219(8) -0.0286(5) 0.4381(5) 0.0716(16) Uani 1 1 d . . .
H6 H 0.2111 0.0311 0.3599 0.086 Uiso 1 1 calc R . .
C7 C 0.3234(6) -0.0505(4) 0.7553(4) 0.0555(12) Uani 1 1 d . . .
C8 C 0.3087(6) 0.0916(4) 0.7447(4) 0.0532(12) Uani 1 1 d . . .
H8A H 0.3972 0.1218 0.6854 0.064 Uiso 1 1 calc R . .
H8B H 0.2029 0.1438 0.7140 0.064 Uiso 1 1 calc R . .
C9 C 0.3700(5) 0.2316(4) 0.8566(4) 0.0480(11) Uani 1 1 d . . .
H9A H 0.4762 0.2303 0.8063 0.058 Uiso 1 1 calc R . .
H9B H 0.3872 0.2310 0.9391 0.058 Uiso 1 1 calc R . .
C10 C 0.2477(6) 0.3585(4) 0.8008(4) 0.0517(11) Uani 1 1 d . . .
C11 C 0.1680(5) 0.0906(4) 0.9562(4) 0.0500(11) Uani 1 1 d . . .
H11A H 0.1122 0.0384 0.9309 0.060 Uiso 1 1 calc R . .
H11B H 0.0915 0.1750 0.9518 0.060 Uiso 1 1 calc R . .
C12 C 0.2087(6) 0.0251(4) 1.0892(4) 0.0487(11) Uani 1 1 d . . .
C13 C 0.1996(8) 0.4666(7) 0.3961(7) 0.098(2) Uani 1 1 d . . .
H13A H 0.1754 0.5551 0.4020 0.117 Uiso 1 1 calc R . .
H13B H 0.1128 0.4270 0.4482 0.117 Uiso 1 1 calc R . .
C14 C 0.3571(9) 0.3961(8) 0.4476(7) 0.106(2) Uani 1 1 d . . .
H14A H 0.3836 0.3080 0.4427 0.159 Uiso 1 1 calc R . .
H14B H 0.3482 0.3960 0.5331 0.159 Uiso 1 1 calc R . .
H14C H 0.4436 0.4377 0.4011 0.159 Uiso 1 1 calc R . .
C15 C 0.2042(11) 0.3392(7) 0.2507(7) 0.110(3) Uani 1 1 d . . .
H15A H 0.3217 0.2990 0.2363 0.133 Uiso 1 1 calc R . .
H15B H 0.1614 0.2868 0.3289 0.133 Uiso 1 1 calc R . .
C16 C 0.1156(11) 0.3374(8) 0.1489(8) 0.116(3) Uani 1 1 d . . .
H16A H 0.0005 0.3820 0.1591 0.174 Uiso 1 1 calc R . .
H16B H 0.1231 0.2488 0.1518 0.174 Uiso 1 1 calc R . .
H16C H 0.1659 0.3802 0.0700 0.174 Uiso 1 1 calc R . .
H1N H 0.412(6) 0.044(5) 0.904(4) 0.065(15) Uiso 1 1 d . . .
N1 N 0.3200(5) 0.1089(3) 0.8673(3) 0.0436(9) Uani 1 1 d . . .
N2 N 0.1873(5) 0.4732(4) 0.2623(4) 0.0674(12) Uani 1 1 d . . .
O1 O 0.1500(6) -0.1869(3) 0.3688(3) 0.0757(12) Uani 1 1 d . . .
H1 H 0.1451 -0.1277 0.3038 0.114 Uiso 1 1 calc R . .
O2 O 0.1850(6) -0.3587(3) 0.5890(3) 0.0754(12) Uani 1 1 d . . .
H2 H 0.2091 -0.4074 0.6577 0.113 Uiso 1 1 calc R . .
O3 O 0.3683(5) -0.1321(3) 0.8518(3) 0.0745(11) Uani 1 1 d . . .
O4 O 0.0876(4) -0.0031(4) 1.1647(3) 0.0679(10) Uani 1 1 d . . .
O5 O 0.3526(4) 0.0069(3) 1.1136(3) 0.0642(10) Uani 1 1 d . . .
O6 O 0.2963(5) 0.4583(3) 0.7913(3) 0.0716(11) Uani 1 1 d . . .
O7 O 0.1156(4) 0.3558(3) 0.7678(3) 0.0664(10) Uani 1 1 d . . .
C17A C 0.315(5) 0.553(6) 0.153(5) 0.23(2) Uani 0.50 1 d P . .
C17B C 0.292(3) 0.542(4) 0.189(3) 0.134(11) Uani 0.50 1 d P . .
C18A C 0.284(4) 0.602(3) 0.0518(17) 0.143(9) Uani 0.50 1 d P . .
C18B C 0.276(3) 0.6569(18) 0.121(5) 0.148(11) Uani 0.50 1 d P . .


_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 O1 1.347(5) . ?
C1 C6 1.372(7) . ?
C1 C2 1.404(7) . ?
C2 O2 1.360(5) . ?
C2 C3 1.382(6) . ?
C3 C4 1.391(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(7) . ?
C4 C7 1.466(6) . ?
C5 C6 1.386(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O3 1.224(5) . ?
C7 C8 1.519(6) . ?
C8 N1 1.485(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.501(5) . ?
C9 C10 1.519(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O7 1.241(5) . ?
C10 O6 1.254(5) . ?
C11 N1 1.502(5) . ?
C11 C12 1.510(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O5 1.233(5) . ?
C12 O4 1.254(5) . ?
C13 C14 1.452(9) . ?
C13 N2 1.518(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.487(10) . ?
C15 N2 1.503(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 H1N 0.95(5) . ?
N2 C17B 1.33(3) . ?
N2 C17A 1.69(3) . ?
O1 H1 0.8200 . ?
O2 H2 0.8200 . ?
C17A C18B 1.07(6) . ?
C17A C18A 1.15(5) . ?
C17B C18B 1.26(4) . ?
C17B C18A 1.50(3) . ?
C18A C18B 1.12(4) . ?

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 C1 C6 122.8(4) . . ?
O1 C1 C2 117.5(4) . . ?
C6 C1 C2 119.6(4) . . ?
O2 C2 C3 123.5(4) . . ?
O2 C2 C1 116.7(4) . . ?
C3 C2 C1 119.8(4) . . ?
C2 C3 C4 120.4(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.5(4) . . ?
C3 C4 C7 118.4(4) . . ?
C5 C4 C7 122.1(4) . . ?
C6 C5 C4 120.0(4) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C1 C6 C5 120.7(4) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
O3 C7 C4 123.2(4) . . ?
O3 C7 C8 118.1(4) . . ?
C4 C7 C8 118.7(4) . . ?
N1 C8 C7 111.0(4) . . ?
N1 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N1 C9 C10 116.0(3) . . ?
N1 C9 H9A 108.3 . . ?
C10 C9 H9A 108.3 . . ?
N1 C9 H9B 108.3 . . ?
C10 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
O7 C10 O6 126.5(4) . . ?
O7 C10 C9 119.7(4) . . ?
O6 C10 C9 113.7(4) . . ?
N1 C11 C12 112.7(4) . . ?
N1 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
N1 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
O5 C12 O4 126.7(4) . . ?
O5 C12 C11 118.5(4) . . ?
O4 C12 C11 114.8(4) . . ?
C14 C13 N2 117.2(6) . . ?
C14 C13 H13A 108.0 . . ?
N2 C13 H13A 108.0 . . ?
C14 C13 H13B 108.0 . . ?
N2 C13 H13B 108.0 . . ?
H13A C13 H13B 107.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 N2 114.1(6) . . ?
C16 C15 H15A 108.7 . . ?
N2 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
N2 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 N1 C9 113.2(3) . . ?
C8 N1 C11 112.4(3) . . ?
C9 N1 C11 113.7(3) . . ?
C8 N1 H1N 109(3) . . ?
C9 N1 H1N 101(3) . . ?
C11 N1 H1N 107(3) . . ?
C17B N2 C15 117(2) . . ?
C17B N2 C13 108.1(19) . . ?
C15 N2 C13 110.3(5) . . ?
C17B N2 C17A 8(4) . . ?
C15 N2 C17A 111(3) . . ?
C13 N2 C17A 116(3) . . ?
C1 O1 H1 109.5 . . ?
C2 O2 H2 109.5 . . ?
C18B C17A C18A 60(3) . . ?
C18B C17A N2 118(5) . . ?
C18A C17A N2 123(5) . . ?
C18B C17B N2 135(2) . . ?
C18B C17B C18A 46.7(18) . . ?
N2 C17B C18A 124(3) . . ?
C18B C18A C17A 56(3) . . ?
C18B C18A C17B 55(3) . . ?
C17A C18A C17B 10(2) . . ?
C17A C18B C18A 63(4) . . ?
C17A C18B C17B 18(4) . . ?
C18A C18B C17B 78(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O6 0.82 1.85 2.658(5) 166.6 1_545
O1 H1 O4 0.82 1.78 2.588(5) 167.0 1_554
N1 H1N O5 0.95(5) 1.89(5) 2.703(5) 142(4) 2_657

_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.957
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 987980'
