# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2013


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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 
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#  except for the purpose of generating routine backup copies 
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data_ro11
_database_code_depnum_ccdc_archive 'CCDC 904928'
#TrackingRef 'web_deposit_cif_file_0_FranziskaEmmerling_1353515298.RO11rev2.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H41 Cu N5 O12'
_chemical_formula_weight         631.14

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   p_b_c_a

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                   17.319(13)
_cell_length_b                   15.007(13)
_cell_length_c                   21.514(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5592(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    211
_cell_measurement_theta_min      4
_cell_measurement_theta_max      27

_exptl_crystal_description       block
_exptl_crystal_colour            bluegreen
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2664
_exptl_absorpt_coefficient_mu    0.851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .45
_exptl_absorpt_correction_T_max  .56
_exptl_absorpt_process_details   'SADABS (Bruker. 2005)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      273(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 APEX CCD area-detector'
_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            15484
_diffrn_reflns_av_R_equivalents  0.2335
_diffrn_reflns_av_sigmaI/netI    0.3548
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5378
_reflns_number_gt                2284
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'SHELXTL (Bruker, 2001), ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0058P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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       0.00039(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         5378
_refine_ls_number_parameters     362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2678
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.0937
_refine_ls_wR_factor_gt          0.0732
_refine_ls_goodness_of_fit_ref   0.671
_refine_ls_restrained_S_all      0.671
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.001

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
Cu1 Cu 0.02352(4) 0.24106(5) 0.37254(5) 0.0413(2) Uani 1 1 d . . .
N1 N -0.0473(4) 0.2803(5) 0.4443(3) 0.0587(19) Uani 1 1 d . . .
N2 N -0.0187(3) 0.1129(3) 0.3727(3) 0.0479(13) Uani 1 1 d . . .
N3 N 0.0979(3) 0.1985(4) 0.3007(3) 0.0499(17) Uani 1 1 d . . .
N4 N 0.0997(3) 0.3384(4) 0.4055(3) 0.0491(16) Uani 1 1 d . . .
O1 O -0.1426(3) 0.3825(3) 0.2654(2) 0.0636(16) Uani 1 1 d . . .
O2 O -0.0477(3) 0.3074(3) 0.3078(2) 0.0460(13) Uani 1 1 d . . .
O3 O -0.2435(3) 0.0671(4) 0.3098(3) 0.110(2) Uani 1 1 d . . .
O4 O -0.2154(3) -0.0682(3) 0.2780(2) 0.0720(17) Uani 1 1 d . . .
H4 H -0.2610 -0.0697 0.2678 0.108 Uiso 1 1 calc R . .
O5 O 0.1810(3) 0.2827(3) 0.0950(2) 0.0806(18) Uani 1 1 d . . .
H5 H 0.1702 0.3135 0.0647 0.121 Uiso 1 1 calc R . .
O6 O 0.0634(3) 0.3203(3) 0.1234(3) 0.0664(15) Uani 1 1 d . . .
O7 O 0.1413(3) 0.6518(3) 0.3657(3) 0.113(2) Uani 1 1 d . . .
H7 H 0.1176 0.6947 0.3519 0.169 Uiso 1 1 calc R . .
O8 O 0.0378(4) 0.5906(3) 0.3471(3) 0.143(3) Uani 1 1 d . . .
C1 C -0.0555(6) 0.2186(7) 0.4955(4) 0.110(4) Uani 1 1 d . . .
H1A H -0.0911 0.2430 0.5258 0.132 Uiso 1 1 calc R . .
H1B H -0.0059 0.2106 0.5157 0.132 Uiso 1 1 calc R . .
C2 C -0.0850(5) 0.1294(7) 0.4731(4) 0.096(3) Uani 1 1 d . . .
H2A H -0.0995 0.0944 0.5092 0.116 Uiso 1 1 calc R . .
H2B H -0.1316 0.1396 0.4490 0.116 Uiso 1 1 calc R . .
C3 C -0.0327(5) 0.0773(6) 0.4359(4) 0.074(3) Uani 1 1 d . . .
H3A H -0.0532 0.0174 0.4323 0.089 Uiso 1 1 calc R . .
H3B H 0.0163 0.0733 0.4576 0.089 Uiso 1 1 calc R . .
C4 C 0.0448(5) 0.0569(4) 0.3466(4) 0.067(3) Uani 1 1 d . . .
H4A H 0.0260 -0.0026 0.3377 0.080 Uiso 1 1 calc R . .
H4B H 0.0868 0.0524 0.3762 0.080 Uiso 1 1 calc R . .
C5 C 0.0721(5) 0.1012(6) 0.2880(4) 0.095(3) Uani 1 1 d . . .
H5A H 0.0306 0.1012 0.2577 0.114 Uiso 1 1 calc R . .
H5B H 0.1150 0.0678 0.2708 0.114 Uiso 1 1 calc R . .
C6 C 0.1745(5) 0.1885(6) 0.3206(4) 0.083(3) Uani 1 1 d . . .
H6A H 0.2060 0.1664 0.2867 0.100 Uiso 1 1 calc R . .
H6B H 0.1768 0.1456 0.3543 0.100 Uiso 1 1 calc R . .
C7 C 0.2068(4) 0.2814(5) 0.3435(4) 0.086(3) Uani 1 1 d . . .
H7A H 0.2627 0.2780 0.3443 0.104 Uiso 1 1 calc R . .
H7B H 0.1927 0.3262 0.3131 0.104 Uiso 1 1 calc R . .
C8 C 0.1809(4) 0.3112(5) 0.4037(4) 0.068(3) Uani 1 1 d . . .
H8A H 0.2126 0.3612 0.4167 0.082 Uiso 1 1 calc R . .
H8B H 0.1886 0.2635 0.4335 0.082 Uiso 1 1 calc R . .
C9 C 0.0780(6) 0.3528(5) 0.4721(4) 0.087(3) Uani 1 1 d . . .
H9A H 0.1007 0.4078 0.4873 0.104 Uiso 1 1 calc R . .
H9B H 0.0971 0.3040 0.4974 0.104 Uiso 1 1 calc R . .
C10 C -0.0095(6) 0.3577(6) 0.4763(5) 0.118(4) Uani 1 1 d . . .
H10A H -0.0248 0.3585 0.5196 0.142 Uiso 1 1 calc R . .
H10B H -0.0271 0.4128 0.4573 0.142 Uiso 1 1 calc R . .
C11 C -0.1256(5) 0.3115(6) 0.4271(3) 0.084(3) Uani 1 1 d . . .
H11A H -0.1476 0.3396 0.4636 0.101 Uiso 1 1 calc R . .
H11B H -0.1565 0.2589 0.4187 0.101 Uiso 1 1 calc R . .
C12 C -0.1374(4) 0.3738(5) 0.3740(4) 0.084(3) Uani 1 1 d . . .
H12A H -0.1926 0.3825 0.3697 0.101 Uiso 1 1 calc R . .
H12B H -0.1157 0.4308 0.3863 0.101 Uiso 1 1 calc R . .
C13 C -0.1068(4) 0.3531(5) 0.3110(4) 0.045(2) Uani 1 1 d . . .
C14 C -0.0871(4) 0.1076(4) 0.3329(3) 0.049(2) Uani 1 1 d . . .
H14A H -0.0752 0.1368 0.2939 0.059 Uiso 1 1 calc R . .
H14B H -0.1281 0.1416 0.3526 0.059 Uiso 1 1 calc R . .
C15 C -0.1193(4) 0.0129(4) 0.3179(3) 0.058(2) Uani 1 1 d . . .
H15A H -0.0880 -0.0125 0.2850 0.070 Uiso 1 1 calc R . .
H15B H -0.1123 -0.0241 0.3544 0.070 Uiso 1 1 calc R . .
C16 C -0.1995(4) 0.0074(5) 0.2993(4) 0.052(2) Uani 1 1 d . . .
C17 C 0.0882(4) 0.2485(6) 0.2426(3) 0.063(2) Uani 1 1 d . . .
H17A H 0.0970 0.3111 0.2515 0.076 Uiso 1 1 calc R . .
H17B H 0.0348 0.2426 0.2297 0.076 Uiso 1 1 calc R . .
C18 C 0.1378(4) 0.2236(5) 0.1889(3) 0.061(2) Uani 1 1 d . . .
H18A H 0.1294 0.1613 0.1789 0.073 Uiso 1 1 calc R . .
H18B H 0.1916 0.2306 0.2006 0.073 Uiso 1 1 calc R . .
C19 C 0.1217(4) 0.2792(5) 0.1324(4) 0.058(2) Uani 1 1 d . . .
C20 C 0.0853(3) 0.4202(4) 0.3677(4) 0.057(2) Uani 1 1 d . . .
H20A H 0.0312 0.4359 0.3717 0.069 Uiso 1 1 calc R . .
H20B H 0.0946 0.4060 0.3244 0.069 Uiso 1 1 calc R . .
C21 C 0.1328(4) 0.5004(4) 0.3843(4) 0.073(2) Uani 1 1 d . . .
H21A H 0.1377 0.5035 0.4292 0.088 Uiso 1 1 calc R . .
H21B H 0.1842 0.4932 0.3671 0.088 Uiso 1 1 calc R . .
C22 C 0.1004(5) 0.5839(5) 0.3619(4) 0.063(3) Uani 1 1 d . . .
N5 N 0.1949(4) 0.0588(6) 0.4869(4) 0.102(3) Uani 1 1 d . . .
O9 O 0.1518(4) 0.1202(4) 0.4923(3) 0.1154(15) Uani 1 1 d . . .
O10 O 0.2421(4) 0.0399(4) 0.5236(3) 0.1154(15) Uani 1 1 d . . .
O11 O 0.1914(4) 0.0081(5) 0.4401(3) 0.1154(15) Uani 1 1 d . . .
O12 O 0.0901(3) 0.8060(3) 0.3419(2) 0.0613(15) Uani 1 1 d . . .
H12F H 0.0371 0.8087 0.3421 0.074 Uiso 1 1 d G . .
H12E H 0.1108 0.8275 0.3887 0.074 Uiso 1 1 d G . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0400(4) 0.0407(5) 0.0432(4) 0.0023(5) -0.0033(6) -0.0013(5)
N1 0.047(5) 0.073(5) 0.057(4) 0.013(4) 0.000(4) 0.008(4)
N2 0.040(3) 0.043(3) 0.061(4) 0.018(4) -0.023(4) -0.009(3)
N3 0.032(4) 0.057(4) 0.061(5) 0.015(4) 0.004(4) 0.016(3)
N4 0.055(4) 0.035(4) 0.058(4) 0.010(3) -0.016(4) -0.002(3)
O1 0.055(4) 0.077(4) 0.059(4) 0.003(3) -0.005(3) 0.027(3)
O2 0.041(3) 0.057(3) 0.040(3) 0.013(3) 0.021(3) 0.017(3)
O3 0.082(5) 0.065(4) 0.185(6) -0.052(4) -0.069(5) 0.013(4)
O4 0.040(3) 0.065(4) 0.111(5) -0.031(4) 0.014(3) -0.008(3)
O5 0.074(4) 0.102(5) 0.066(3) 0.005(3) 0.016(3) 0.021(3)
O6 0.037(3) 0.095(4) 0.067(3) 0.022(4) 0.003(4) 0.006(3)
O7 0.078(4) 0.044(4) 0.216(7) 0.030(5) -0.013(5) -0.010(3)
O8 0.106(5) 0.056(4) 0.268(10) 0.022(4) -0.095(6) -0.016(4)
C1 0.126(10) 0.127(10) 0.077(7) 0.025(8) 0.020(7) 0.034(8)
C2 0.089(8) 0.120(10) 0.080(8) 0.010(7) -0.001(7) -0.023(8)
C3 0.053(6) 0.098(7) 0.071(7) 0.036(6) -0.011(6) -0.026(6)
C4 0.081(7) 0.026(4) 0.092(7) 0.009(5) -0.034(6) -0.012(4)
C5 0.098(8) 0.066(7) 0.121(9) -0.051(7) 0.002(7) 0.003(6)
C6 0.059(6) 0.129(9) 0.061(6) 0.004(6) 0.002(6) 0.016(6)
C7 0.043(5) 0.053(7) 0.164(10) 0.027(6) 0.001(7) -0.014(5)
C8 0.047(6) 0.054(6) 0.103(7) -0.001(5) -0.022(6) 0.002(5)
C9 0.124(9) 0.064(7) 0.072(7) -0.011(5) -0.038(7) -0.029(7)
C10 0.128(10) 0.107(9) 0.120(9) -0.054(7) 0.059(9) -0.018(8)
C11 0.068(7) 0.132(9) 0.052(6) 0.002(6) 0.014(6) 0.016(6)
C12 0.081(6) 0.100(7) 0.071(6) 0.029(7) -0.005(7) 0.026(5)
C13 0.032(5) 0.070(6) 0.032(5) -0.007(5) 0.010(5) 0.005(4)
C14 0.053(5) 0.033(5) 0.062(5) -0.006(4) -0.020(4) -0.009(4)
C15 0.058(5) 0.039(5) 0.077(6) -0.002(4) -0.014(5) -0.006(4)
C16 0.037(6) 0.043(6) 0.077(7) -0.003(5) -0.015(5) 0.003(5)
C17 0.040(5) 0.083(6) 0.067(5) 0.002(6) 0.011(4) 0.003(5)
C18 0.068(6) 0.063(6) 0.052(5) 0.010(5) 0.021(5) 0.007(4)
C19 0.046(5) 0.088(7) 0.040(5) -0.025(5) 0.018(5) 0.000(5)
C20 0.050(5) 0.028(4) 0.093(6) -0.005(5) -0.027(5) 0.001(4)
C21 0.082(6) 0.041(5) 0.097(7) -0.010(5) -0.031(6) 0.005(5)
C22 0.048(5) 0.047(6) 0.094(7) -0.004(5) -0.042(6) -0.016(5)
N5 0.061(6) 0.128(8) 0.116(7) 0.058(6) -0.069(6) -0.046(5)
O9 0.110(3) 0.118(4) 0.118(4) -0.024(3) -0.018(3) 0.022(3)
O10 0.110(3) 0.118(4) 0.118(4) -0.024(3) -0.018(3) 0.022(3)
O11 0.110(3) 0.118(4) 0.118(4) -0.024(3) -0.018(3) 0.022(3)
O12 0.044(3) 0.081(4) 0.059(3) -0.012(3) -0.007(3) -0.007(3)

_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
Cu1 N1 2.058(6) . ?
Cu1 N2 2.058(5) . ?
Cu1 N4 2.092(6) . ?
Cu1 O2 2.110(5) . ?
Cu1 N3 2.112(6) . ?
N1 C1 1.445(9) . ?
N1 C11 1.482(8) . ?
N1 C10 1.501(10) . ?
N2 C14 1.465(7) . ?
N2 C3 1.482(8) . ?
N2 C4 1.492(8) . ?
N3 C6 1.402(8) . ?
N3 C17 1.468(7) . ?
N3 C5 1.552(9) . ?
N4 C8 1.464(8) . ?
N4 C20 1.494(7) . ?
N4 C9 1.497(8) . ?
O1 C13 1.243(8) . ?
O2 C13 1.234(7) . ?
O3 C16 1.197(7) . ?
O4 C16 1.254(8) . ?
O4 H4 0.8200 . ?
O5 C19 1.306(8) . ?
O5 H5 0.8200 . ?
O6 C19 1.200(7) . ?
O7 C22 1.243(7) . ?
O7 H7 0.8200 . ?
O8 C22 1.135(7) . ?
C1 C2 1.512(10) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.439(10) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.502(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.580(10) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.443(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.520(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.490(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.488(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 C15 1.559(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.449(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C17 C18 1.487(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.501(9) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C20 C21 1.501(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.455(9) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
N5 O10 1.171(8) . ?
N5 O9 1.191(9) . ?
N5 O11 1.263(9) . ?
O12 H12F 0.92(6) . ?
O12 H12E 1.1156 . ?

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 Cu1 N2 93.1(3) . . ?
N1 Cu1 N4 85.5(3) . . ?
N2 Cu1 N4 151.2(2) . . ?
N1 Cu1 O2 90.7(2) . . ?
N2 Cu1 O2 103.6(2) . . ?
N4 Cu1 O2 105.2(2) . . ?
N1 Cu1 N3 178.4(3) . . ?
N2 Cu1 N3 86.3(2) . . ?
N4 Cu1 N3 94.3(2) . . ?
O2 Cu1 N3 90.9(2) . . ?
C1 N1 C11 107.6(7) . . ?
C1 N1 C10 100.9(8) . . ?
C11 N1 C10 105.6(7) . . ?
C1 N1 Cu1 116.6(5) . . ?
C11 N1 Cu1 116.6(5) . . ?
C10 N1 Cu1 107.8(5) . . ?
C14 N2 C3 112.6(6) . . ?
C14 N2 C4 110.3(6) . . ?
C3 N2 C4 105.3(6) . . ?
C14 N2 Cu1 109.7(4) . . ?
C3 N2 Cu1 113.3(5) . . ?
C4 N2 Cu1 105.3(4) . . ?
C6 N3 C17 115.1(6) . . ?
C6 N3 C5 103.1(6) . . ?
C17 N3 C5 107.4(7) . . ?
C6 N3 Cu1 112.7(5) . . ?
C17 N3 Cu1 113.5(4) . . ?
C5 N3 Cu1 103.7(4) . . ?
C8 N4 C20 112.0(6) . . ?
C8 N4 C9 107.8(7) . . ?
C20 N4 C9 111.1(6) . . ?
C8 N4 Cu1 113.7(5) . . ?
C20 N4 Cu1 106.5(4) . . ?
C9 N4 Cu1 105.5(4) . . ?
C13 O2 Cu1 135.2(5) . . ?
C16 O4 H4 109.5 . . ?
C19 O5 H5 109.5 . . ?
C22 O7 H7 109.5 . . ?
N1 C1 C2 110.9(8) . . ?
N1 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.0 . . ?
C3 C2 C1 116.4(8) . . ?
C3 C2 H2A 108.2 . . ?
C1 C2 H2A 108.2 . . ?
C3 C2 H2B 108.2 . . ?
C1 C2 H2B 108.2 . . ?
H2A C2 H2B 107.3 . . ?
C2 C3 N2 114.7(7) . . ?
C2 C3 H3A 108.6 . . ?
N2 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
N2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
N2 C4 C5 107.3(6) . . ?
N2 C4 H4A 110.2 . . ?
C5 C4 H4A 110.2 . . ?
N2 C4 H4B 110.2 . . ?
C5 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
C4 C5 N3 111.1(6) . . ?
C4 C5 H5A 109.4 . . ?
N3 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
N3 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
N3 C6 C7 109.6(7) . . ?
N3 C6 H6A 109.7 . . ?
C7 C6 H6A 109.7 . . ?
N3 C6 H6B 109.7 . . ?
C7 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 C6 116.4(7) . . ?
C8 C7 H7A 108.2 . . ?
C6 C7 H7A 108.2 . . ?
C8 C7 H7B 108.2 . . ?
C6 C7 H7B 108.2 . . ?
H7A C7 H7B 107.3 . . ?
C7 C8 N4 114.1(7) . . ?
C7 C8 H8A 108.7 . . ?
N4 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
N4 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N4 C9 C10 108.3(7) . . ?
N4 C9 H9A 110.0 . . ?
C10 C9 H9A 110.0 . . ?
N4 C9 H9B 110.0 . . ?
C10 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
N1 C10 C9 111.7(7) . . ?
N1 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
N1 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
N1 C11 C12 121.0(7) . . ?
N1 C11 H11A 107.1 . . ?
C12 C11 H11A 107.1 . . ?
N1 C11 H11B 107.1 . . ?
C12 C11 H11B 107.1 . . ?
H11A C11 H11B 106.8 . . ?
C13 C12 C11 121.2(7) . . ?
C13 C12 H12A 107.0 . . ?
C11 C12 H12A 107.0 . . ?
C13 C12 H12B 107.0 . . ?
C11 C12 H12B 107.0 . . ?
H12A C12 H12B 106.8 . . ?
O2 C13 O1 124.5(7) . . ?
O2 C13 C12 117.6(7) . . ?
O1 C13 C12 117.9(7) . . ?
N2 C14 C15 117.3(5) . . ?
N2 C14 H14A 108.0 . . ?
C15 C14 H14A 108.0 . . ?
N2 C14 H14B 108.0 . . ?
C15 C14 H14B 108.0 . . ?
H14A C14 H14B 107.2 . . ?
C16 C15 C14 116.9(6) . . ?
C16 C15 H15A 108.1 . . ?
C14 C15 H15A 108.1 . . ?
C16 C15 H15B 108.1 . . ?
C14 C15 H15B 108.1 . . ?
H15A C15 H15B 107.3 . . ?
O3 C16 O4 127.3(7) . . ?
O3 C16 C15 121.0(8) . . ?
O4 C16 C15 111.3(7) . . ?
N3 C17 C18 117.7(6) . . ?
N3 C17 H17A 107.9 . . ?
C18 C17 H17A 107.9 . . ?
N3 C17 H17B 107.9 . . ?
C18 C17 H17B 107.9 . . ?
H17A C17 H17B 107.2 . . ?
C17 C18 C19 112.4(6) . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
O6 C19 O5 122.7(9) . . ?
O6 C19 C18 125.0(8) . . ?
O5 C19 C18 112.1(7) . . ?
N4 C20 C21 116.0(6) . . ?
N4 C20 H20A 108.3 . . ?
C21 C20 H20A 108.3 . . ?
N4 C20 H20B 108.3 . . ?
C21 C20 H20B 108.3 . . ?
H20A C20 H20B 107.4 . . ?
C22 C21 C20 113.6(6) . . ?
C22 C21 H21A 108.8 . . ?
C20 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
C20 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
O8 C22 O7 119.4(8) . . ?
O8 C22 C21 122.5(8) . . ?
O7 C22 C21 117.7(7) . . ?
O10 N5 O9 123.9(11) . . ?
O10 N5 O11 115.2(11) . . ?
O9 N5 O11 120.9(9) . . ?
H12F O12 H12E 107.8 . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.084


data_ro12
_database_code_depnum_ccdc_archive 'CCDC 904929'
#TrackingRef 'web_deposit_cif_file_1_FranziskaEmmerling_1353515298.RO12rev2.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H40 N4 O8, 5(H2 O)'
_chemical_formula_sum            ' C22 H50 N4 O13 '
_chemical_formula_weight         578.66

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 '
_symmetry_space_group_name_hall  '-P 1 '

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

_cell_length_a                   7.833(10)
_cell_length_b                   9.223(12)
_cell_length_c                   11.953(16)
_cell_angle_alpha                106.960(14)
_cell_angle_beta                 105.082(13)
_cell_angle_gamma                100.538(14)
_cell_volume                     765.6(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    156
_cell_measurement_theta_min      4
_cell_measurement_theta_max      27

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             314
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .976
_exptl_absorpt_correction_T_max  .98
_exptl_absorpt_process_details   'SADABS (Bruker. 2005)'

_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  'Bruker APEX CCD area-detector'
_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            4091
_diffrn_reflns_av_R_equivalents  0.1255
_diffrn_reflns_av_sigmaI/netI    0.8055
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         27.77
_reflns_number_total             3301
_reflns_number_gt                1517
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'SHELXTL (Bruker, 2001), ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'


_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0959P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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       0.045(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3301
_refine_ls_number_parameters     202
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.4343
_refine_ls_R_factor_gt           0.0849
_refine_ls_wR_factor_ref         0.2809
_refine_ls_wR_factor_gt          0.1808
_refine_ls_goodness_of_fit_ref   0.712
_refine_ls_restrained_S_all      0.711
_refine_ls_shift/su_max          0.088
_refine_ls_shift/su_mean         0.005

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
O1 O 0.0823(8) 0.4646(7) 0.3073(6) 0.078(2) Uani 1 1 d . . .
H1 H 0.0114 0.5199 0.3076 0.118 Uiso 1 1 calc R . .
O2 O -0.0254(8) 0.3612(7) 0.4338(6) 0.084(2) Uani 1 1 d . . .
O3 O 0.7267(11) 0.1868(8) 0.9541(7) 0.109(3) Uani 1 1 d . . .
H3 H 0.7444 0.1073 0.9671 0.163 Uiso 1 1 calc R . .
O4 O 0.4420(10) 0.0841(6) 0.9426(6) 0.088(2) Uani 1 1 d . . .
N1 N 0.3480(9) 0.2509(7) 0.3102(6) 0.0407(19) Uani 1 1 d . . .
N2 N 0.5775(8) 0.4484(7) 0.7197(6) 0.0423(19) Uani 1 1 d . . .
C1 C 0.0193(12) 0.3448(11) 0.3358(10) 0.061(3) Uani 1 1 d . . .
C2 C 0.0063(12) 0.1831(10) 0.2532(8) 0.069(3) Uani 1 1 d . . .
H2A H -0.1066 0.1461 0.1829 0.083 Uiso 1 1 calc R . .
H2B H -0.0011 0.1119 0.2987 0.083 Uiso 1 1 calc R . .
C3 C 0.1697(13) 0.1754(9) 0.2047(8) 0.070(3) Uani 1 1 d . . .
H3A H 0.1617 0.0661 0.1619 0.085 Uiso 1 1 calc R . .
H3B H 0.1647 0.2297 0.1460 0.085 Uiso 1 1 calc R . .
C4 C 0.5086(11) 0.2929(8) 0.2689(7) 0.047(2) Uani 1 1 d . . .
H4A H 0.5158 0.1984 0.2098 0.057 Uiso 1 1 calc R . .
H4B H 0.6209 0.3318 0.3399 0.057 Uiso 1 1 calc R . .
C6 C 0.3831(12) 0.1455(8) 0.3818(7) 0.057(3) Uani 1 1 d . . .
H6A H 0.4327 0.0664 0.3384 0.069 Uiso 1 1 calc R . .
H6B H 0.2667 0.0909 0.3843 0.069 Uiso 1 1 calc R . .
C7 C 0.5159(11) 0.2308(9) 0.5148(7) 0.056(3) Uani 1 1 d . . .
H7A H 0.5405 0.1536 0.5526 0.067 Uiso 1 1 calc R . .
H7B H 0.6317 0.2883 0.5135 0.067 Uiso 1 1 calc R . .
C8 C 0.4374(10) 0.3458(9) 0.5930(7) 0.046(2) Uani 1 1 d . . .
H8A H 0.3963 0.4131 0.5490 0.055 Uiso 1 1 calc R . .
H8B H 0.3312 0.2865 0.6039 0.055 Uiso 1 1 calc R . .
C5 C 0.4960(11) 0.4218(9) 0.2071(7) 0.054(3) Uani 1 1 d . . .
H5A H 0.6169 0.4696 0.2068 0.065 Uiso 1 1 calc R . .
H5B H 0.4140 0.3725 0.1218 0.065 Uiso 1 1 calc R . .
C9 C 0.6426(11) 0.3575(9) 0.8027(7) 0.058(3) Uani 1 1 d . . .
H9A H 0.7342 0.4315 0.8798 0.069 Uiso 1 1 calc R . .
H9B H 0.7019 0.2847 0.7623 0.069 Uiso 1 1 calc R . .
C10 C 0.4867(12) 0.2630(9) 0.8330(8) 0.072(3) Uani 1 1 d . . .
H10A H 0.3940 0.1891 0.7563 0.086 Uiso 1 1 calc R . .
H10B H 0.4285 0.3353 0.8752 0.086 Uiso 1 1 calc R . .
C11 C 0.5602(16) 0.1708(11) 0.9161(9) 0.065(3) Uani 1 1 d . . .
O5 O -0.0253(9) 0.7522(11) 0.3184(9) 0.187(4) Uani 1 1 d D . .
H11 H 0.024(7) 0.779(10) 0.270(4) 0.281 Uiso 1 1 d D . .
H12 H 0.053(7) 0.785(15) 0.391(3) 0.281 Uiso 1 1 d D . .
O6 O 0.0842(12) 0.2817(10) -0.0718(8) 0.208(5) Uani 1 1 d D . .
H13 H 0.038(5) 0.307(7) -0.014(3) 0.312 Uiso 1 1 d D . .
H14 H 0.113(14) 0.361(5) -0.093(7) 0.312 Uiso 1 1 d D . .
O7 O 0.1129(18) -0.0327(15) 0.5305(14) 0.137(6) Uani 0.50 1 d PD . .
H15 H 0.223(3) -0.031(8) 0.535(9) 0.205 Uiso 0.50 1 d PD . .
H16 H 0.064(11) -0.111(10) 0.547(13) 0.205 Uiso 0.50 1 d PD . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.093(5) 0.077(5) 0.104(5) 0.058(4) 0.048(4) 0.050(4)
O2 0.067(5) 0.111(5) 0.101(5) 0.064(4) 0.044(4) 0.021(4)
O3 0.141(7) 0.099(5) 0.112(6) 0.087(5) 0.032(6) 0.028(5)
O4 0.123(6) 0.060(4) 0.080(5) 0.041(3) 0.040(4) -0.010(4)
N1 0.043(5) 0.047(4) 0.042(4) 0.031(3) 0.012(4) 0.012(3)
N2 0.056(5) 0.030(4) 0.045(4) 0.017(3) 0.016(4) 0.016(4)
C1 0.034(6) 0.061(7) 0.096(9) 0.043(7) 0.010(6) 0.024(5)
C2 0.043(7) 0.071(7) 0.088(8) 0.040(6) 0.013(6) 0.000(5)
C3 0.070(8) 0.062(6) 0.070(7) 0.037(5) 0.005(6) 0.002(5)
C4 0.053(6) 0.046(6) 0.051(6) 0.024(4) 0.017(5) 0.021(5)
C6 0.086(7) 0.042(6) 0.049(6) 0.020(5) 0.029(6) 0.014(5)
C7 0.071(7) 0.042(5) 0.056(6) 0.029(5) 0.019(6) 0.002(5)
C8 0.040(6) 0.049(5) 0.053(6) 0.027(5) 0.016(5) 0.010(5)
C5 0.062(7) 0.056(6) 0.068(6) 0.039(5) 0.036(5) 0.023(5)
C9 0.070(7) 0.059(6) 0.054(6) 0.025(5) 0.032(5) 0.018(5)
C10 0.104(8) 0.050(6) 0.085(7) 0.046(5) 0.048(6) 0.018(5)
C11 0.081(9) 0.063(7) 0.061(7) 0.030(6) 0.026(7) 0.022(7)
O5 0.122(7) 0.241(9) 0.361(12) 0.236(9) 0.151(8) 0.119(7)
O6 0.130(8) 0.256(10) 0.173(9) 0.129(8) -0.027(7) -0.070(7)
O7 0.212(18) 0.091(11) 0.169(14) 0.063(10) 0.147(14) 0.036(11)

_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
O1 C1 1.299(10) . ?
O1 H1 0.8200 . ?
O2 C1 1.283(10) . ?
O3 C11 1.229(11) . ?
O3 H3 0.8200 . ?
O4 C11 1.275(11) . ?
N1 C6 1.488(8) . ?
N1 C4 1.495(9) . ?
N1 C3 1.497(9) . ?
N2 C8 1.520(8) . ?
N2 C9 1.525(9) . ?
N2 C5 1.560(9) 2_666 ?
C1 C2 1.498(11) . ?
C2 C3 1.541(11) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.577(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 C7 1.529(9) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.528(10) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C5 N2 1.560(9) 2_666 ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C9 C10 1.552(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.554(12) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
O5 H11 0.847(10) . ?
O5 H12 0.849(10) . ?
O6 H13 0.850(10) . ?
O6 H14 0.852(10) . ?
O7 H15 0.849(10) . ?
O7 H16 0.850(11) . ?

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
C1 O1 H1 109.5 . . ?
C11 O3 H3 109.5 . . ?
C6 N1 C4 109.2(6) . . ?
C6 N1 C3 110.6(6) . . ?
C4 N1 C3 112.8(6) . . ?
C8 N2 C9 114.5(6) . . ?
C8 N2 C5 112.1(6) . 2_666 ?
C9 N2 C5 107.9(6) . 2_666 ?
O2 C1 O1 122.3(9) . . ?
O2 C1 C2 119.4(9) . . ?
O1 C1 C2 118.2(10) . . ?
C1 C2 C3 114.0(7) . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
N1 C3 C2 110.1(7) . . ?
N1 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
N1 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
N1 C4 C5 112.9(6) . . ?
N1 C4 H4A 109.0 . . ?
C5 C4 H4A 109.0 . . ?
N1 C4 H4B 109.0 . . ?
C5 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
N1 C6 C7 114.3(6) . . ?
N1 C6 H6A 108.7 . . ?
C7 C6 H6A 108.7 . . ?
N1 C6 H6B 108.7 . . ?
C7 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C8 C7 C6 111.7(7) . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
N2 C8 C7 112.4(6) . . ?
N2 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
N2 C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
N2 C5 C4 110.2(6) 2_666 . ?
N2 C5 H5A 109.6 2_666 . ?
C4 C5 H5A 109.6 . . ?
N2 C5 H5B 109.6 2_666 . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
N2 C9 C10 114.2(7) . . ?
N2 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
N2 C9 H9B 108.7 . . ?
C10 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 C11 112.0(8) . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
O3 C11 O4 123.8(10) . . ?
O3 C11 C10 119.1(10) . . ?
O4 C11 C10 117.1(10) . . ?
H11 O5 H12 109.9(18) . . ?
H13 O6 H14 109.1(18) . . ?
H15 O7 H16 109.5(18) . . ?

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
O2 C1 C2 C3 -138.4(8) . . . . ?
O1 C1 C2 C3 39.2(11) . . . . ?
C6 N1 C3 C2 75.2(8) . . . . ?
C4 N1 C3 C2 -162.2(6) . . . . ?
C1 C2 C3 N1 51.2(10) . . . . ?
C6 N1 C4 C5 -172.6(6) . . . . ?
C3 N1 C4 C5 64.1(8) . . . . ?
C4 N1 C6 C7 77.4(8) . . . . ?
C3 N1 C6 C7 -157.9(7) . . . . ?
N1 C6 C7 C8 64.2(9) . . . . ?
C9 N2 C8 C7 -63.3(8) . . . . ?
C5 N2 C8 C7 173.5(6) 2_666 . . . ?
C6 C7 C8 N2 -171.9(6) . . . . ?
N1 C4 C5 N2 40.7(8) . . . 2_666 ?
C8 N2 C9 C10 -60.4(8) . . . . ?
C5 N2 C9 C10 65.1(8) 2_666 . . . ?
N2 C9 C10 C11 179.1(7) . . . . ?
C9 C10 C11 O3 3.9(13) . . . . ?
C9 C10 C11 O4 -177.3(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.77
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.055