# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H17 Cu N O9'
_chemical_formula_weight         370.79

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4875(3)
_cell_length_b                   9.4303(3)
_cell_length_c                   10.4406(4)
_cell_angle_alpha                78.225(2)
_cell_angle_beta                 84.542(3)
_cell_angle_gamma                83.261(2)
_cell_volume                     714.78(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2492
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      25.33

_exptl_crystal_description       plate
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_F_000             382
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    1.575
_shelx_estimated_absorpt_T_min   0.609
_shelx_estimated_absorpt_T_max   0.723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5
_exptl_absorpt_correction_T_max  0.7
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5462
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.998
_diffrn_reflns_theta_max         25.385
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2594
_reflns_number_gt                2181
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0517P)²+0.7946P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2594
_refine_ls_number_parameters     224
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.1047
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.065
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7863(5) 1.0033(4) 0.7689(4) 0.0154(8) Uani 1 1 d . . . . .
C2 C 0.8110(5) 1.0932(4) 0.6327(3) 0.0126(8) Uani 1 1 d . . . . .
C3 C 0.8626(5) 1.2326(4) 0.6211(4) 0.0145(8) Uani 1 1 d . . . . .
H3 H 0.8834 1.2644 0.6965 0.017 Uiso 1 1 calc R U . . .
C4 C 0.8838(5) 1.3250(4) 0.5011(4) 0.0141(8) Uani 1 1 d . . . . .
H4 H 0.9208 1.4168 0.4962 0.017 Uiso 1 1 calc R U . . .
C5 C 0.8497(5) 1.2803(4) 0.3875(3) 0.0116(8) Uani 1 1 d . . . . .
C6 C 0.8672(5) 1.3846(4) 0.2567(4) 0.0154(8) Uani 1 1 d . . . . .
C7 C 0.7983(5) 1.1421(4) 0.3959(4) 0.0137(8) Uani 1 1 d . . . . .
H7 H 0.7775 1.1119 0.3197 0.016 Uiso 1 1 calc R U . . .
C8 C 0.7773(5) 1.0475(4) 0.5164(4) 0.0119(8) Uani 1 1 d . . . . .
C9 C 0.6685(5) 0.8437(4) 0.4325(4) 0.0150(8) Uani 1 1 d . . . . .
C10 C 0.6243(5) 0.6901(4) 0.4756(4) 0.0169(8) Uani 1 1 d . . . . .
H10A H 0.7065 0.6302 0.4261 0.020 Uiso 1 1 calc R U . . .
H10B H 0.5038 0.6854 0.4510 0.020 Uiso 1 1 calc R U . . .
C11 C 0.6316(6) 0.6208(4) 0.6208(4) 0.0208(9) Uani 1 1 d . . . . .
H11A H 0.7536 0.6118 0.6449 0.031 Uiso 1 1 calc R U . . .
H11B H 0.5893 0.5261 0.6364 0.031 Uiso 1 1 calc R U . . .
H11C H 0.5564 0.6810 0.6725 0.031 Uiso 1 1 calc R U . . .
Cu1 Cu 0.67523(6) 0.77921(5) 0.96227(4) 0.01321(17) Uani 1 1 d . . . . .
H12A H 0.424(6) 0.919(4) 0.829(3) 0.020 Uiso 1 1 d D U . . .
H13A H 0.823(4) 0.522(5) 0.870(3) 0.020 Uiso 1 1 d D U . . .
H14A H 1.007(4) 0.740(5) 0.962(3) 0.020 Uiso 1 1 d D U . . .
H15A H 0.468(4) 0.638(4) 1.129(4) 0.020 Uiso 1 1 d D U . . .
H12B H 0.353(5) 0.874(4) 0.977(3) 0.020 Uiso 1 1 d D U . . .
H13B H 0.769(5) 0.481(4) 0.993(3) 0.020 Uiso 1 1 d D U . . .
H14B H 0.941(5) 0.681(3) 1.100(3) 0.020 Uiso 1 1 d D U . . .
H15B H 0.661(4) 0.625(4) 1.179(4) 0.020 Uiso 1 1 d D U . . .
N1 N 0.7230(4) 0.9083(3) 0.5256(3) 0.0158(7) Uani 1 1 d . . . . .
H1 H 0.7243 0.8547 0.6028 0.019 Uiso 1 1 calc R U . . .
O1 O 0.7697(3) 0.8683(3) 0.7816(2) 0.0135(6) Uani 1 1 d . . . . .
O2 O 0.7815(4) 1.0652(3) 0.8638(3) 0.0252(7) Uani 1 1 d . . . . .
O3 O 0.9456(4) 1.4953(3) 0.2507(3) 0.0209(6) Uani 1 1 d . . . . .
O4 O 0.7988(4) 1.3534(3) 0.1606(2) 0.0212(6) Uani 1 1 d . . . . .
O5 O 0.6550(4) 0.9052(3) 0.3166(3) 0.0266(7) Uani 1 1 d . . . . .
O12 O 0.4276(4) 0.8481(4) 0.9053(3) 0.0339(8) Uani 1 1 d D . . . .
O13 O 0.7277(4) 0.5338(3) 0.9220(3) 0.0208(6) Uani 1 1 d D . . . .
O14 O 0.9200(5) 0.7601(4) 1.0311(3) 0.0363(8) Uani 1 1 d D . . . .
O15 O 0.5652(5) 0.6894(4) 1.1413(3) 0.0449(9) Uani 1 1 d D . . . .


_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 O2 1.244(5) . ?
C1 O1 1.272(5) . ?
C1 C2 1.506(5) . ?
C2 C3 1.392(5) . ?
C2 C8 1.422(5) . ?
C3 C4 1.379(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(5) . ?
C4 H4 0.9300 . ?
C5 C7 1.385(5) . ?
C5 C6 1.515(5) . ?
C6 O3 1.244(5) . ?
C6 O4 1.270(5) . ?
C7 C8 1.393(5) . ?
C7 H7 0.9300 . ?
C8 N1 1.401(5) . ?
C9 O5 1.238(4) . ?
C9 N1 1.363(5) . ?
C9 C10 1.493(5) . ?
C10 C11 1.527(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
Cu1 O12 1.996(3) . ?
Cu1 O1 2.001(2) . ?
Cu1 O14 2.007(3) . ?
Cu1 O15 2.028(4) . ?
Cu1 O13 2.417(3) . ?
N1 H1 0.8600 . ?
O12 H12A 0.931(19) . ?
O12 H12B 0.945(19) . ?
O13 H13A 0.865(19) . ?
O13 H13B 0.867(19) . ?
O14 H14A 0.955(19) . ?
O14 H14B 0.936(19) . ?
O15 H15A 0.948(19) . ?
O15 H15B 0.947(19) . ?

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 C1 O1 123.0(3) . . ?
O2 C1 C2 118.3(3) . . ?
O1 C1 C2 118.7(3) . . ?
C3 C2 C8 118.1(3) . . ?
C3 C2 C1 117.5(3) . . ?
C8 C2 C1 124.3(3) . . ?
C4 C3 C2 122.0(3) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C7 C5 C4 119.5(3) . . ?
C7 C5 C6 121.2(3) . . ?
C4 C5 C6 119.3(3) . . ?
O3 C6 O4 124.4(3) . . ?
O3 C6 C5 118.3(3) . . ?
O4 C6 C5 117.4(3) . . ?
C5 C7 C8 121.3(3) . . ?
C5 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C7 C8 N1 121.5(3) . . ?
C7 C8 C2 119.3(3) . . ?
N1 C8 C2 119.2(3) . . ?
O5 C9 N1 123.6(4) . . ?
O5 C9 C10 119.6(3) . . ?
N1 C9 C10 116.8(3) . . ?
C9 C10 C11 118.1(3) . . ?
C9 C10 H10A 107.8 . . ?
C11 C10 H10A 107.8 . . ?
C9 C10 H10B 107.8 . . ?
C11 C10 H10B 107.8 . . ?
H10A C10 H10B 107.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O12 Cu1 O1 87.57(12) . . ?
O12 Cu1 O14 165.46(14) . . ?
O1 Cu1 O14 91.89(12) . . ?
O12 Cu1 O15 89.24(14) . . ?
O1 Cu1 O15 176.66(13) . . ?
O14 Cu1 O15 91.45(15) . . ?
O12 Cu1 O13 104.05(12) . . ?
O1 Cu1 O13 93.65(10) . . ?
O14 Cu1 O13 90.48(12) . . ?
O15 Cu1 O13 86.16(13) . . ?
C9 N1 C8 130.7(3) . . ?
C9 N1 H1 114.6 . . ?
C8 N1 H1 114.6 . . ?
C1 O1 Cu1 112.7(2) . . ?
Cu1 O12 H12A 114(3) . . ?
Cu1 O12 H12B 109(2) . . ?
H12A O12 H12B 114(4) . . ?
Cu1 O13 H13A 112(3) . . ?
Cu1 O13 H13B 106(3) . . ?
H13A O13 H13B 98(4) . . ?
Cu1 O14 H14A 107(2) . . ?
Cu1 O14 H14B 114(3) . . ?
H14A O14 H14B 104(4) . . ?
Cu1 O15 H15A 109(3) . . ?
Cu1 O15 H15B 103(3) . . ?
H15A O15 H15B 111(4) . . ?

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 12.5(5) . . . . ?
O1 C1 C2 C3 -168.2(3) . . . . ?
O2 C1 C2 C8 -164.5(4) . . . . ?
O1 C1 C2 C8 14.8(5) . . . . ?
C8 C2 C3 C4 -0.9(5) . . . . ?
C1 C2 C3 C4 -178.1(3) . . . . ?
C2 C3 C4 C5 1.3(5) . . . . ?
C3 C4 C5 C7 -1.3(5) . . . . ?
C3 C4 C5 C6 177.9(3) . . . . ?
C7 C5 C6 O3 -166.6(3) . . . . ?
C4 C5 C6 O3 14.1(5) . . . . ?
C7 C5 C6 O4 14.1(5) . . . . ?
C4 C5 C6 O4 -165.2(3) . . . . ?
C4 C5 C7 C8 1.0(5) . . . . ?
C6 C5 C7 C8 -178.2(3) . . . . ?
C5 C7 C8 N1 179.1(3) . . . . ?
C5 C7 C8 C2 -0.7(5) . . . . ?
C3 C2 C8 C7 0.6(5) . . . . ?
C1 C2 C8 C7 177.6(3) . . . . ?
C3 C2 C8 N1 -179.2(3) . . . . ?
C1 C2 C8 N1 -2.2(5) . . . . ?
O5 C9 C10 C11 -176.4(3) . . . . ?
N1 C9 C10 C11 3.9(5) . . . . ?
O5 C9 N1 C8 -1.4(6) . . . . ?
C10 C9 N1 C8 178.3(3) . . . . ?
C7 C8 N1 C9 -6.0(6) . . . . ?
C2 C8 N1 C9 173.8(4) . . . . ?
O2 C1 O1 Cu1 14.3(4) . . . . ?
C2 C1 O1 Cu1 -165.0(2) . . . . ?

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
O15 H15A O13 0.948(19) 2.48(2) 3.406(5) 166(4) 2_667
C7 H7 O5 0.93 2.26 2.883(5) 124.2 .
N1 H1 O1 0.86 1.96 2.673(4) 139.4 .
O14 H14B O3 0.936(19) 2.10(2) 3.027(4) 171(4) 1_546
O14 H14A O4 0.955(19) 2.08(2) 3.021(5) 166(4) 2_776
O15 H15B O3 0.947(19) 2.43(2) 3.363(5) 169(4) 1_546
O12 H12A O5 0.931(19) 2.08(2) 2.982(4) 164(4) 2_676
O12 H12B O2 0.945(19) 2.01(2) 2.953(4) 174(4) 2_677
O13 H13B O4 0.867(19) 1.92(2) 2.773(4) 166(4) 1_546
O13 H13A O3 0.865(19) 2.05(2) 2.918(4) 177(4) 2_776

_refine_diff_density_max         0.638
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.109

_shelxl_version_number           2014-1

_database_code_depnum_ccdc_archive 'CCDC 1005775'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H15 Cu N O9'
_chemical_formula_weight         356.77

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5580(10)
_cell_length_b                   9.2626(13)
_cell_length_c                   10.5360(14)
_cell_angle_alpha                104.104(4)
_cell_angle_beta                 90.218(4)
_cell_angle_gamma                96.517(5)
_cell_volume                     710.35(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9500
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      25.35

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_F_000             366
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    1.581
_shelx_estimated_absorpt_T_min   0.632
_shelx_estimated_absorpt_T_max   0.753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6
_exptl_absorpt_correction_T_max  0.7
_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_measurement_device_type  'Bruker APEX-II PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17154
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.283
_diffrn_reflns_theta_max         25.529
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2607
_reflns_number_gt                2451
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0676P)²+0.6598P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2607
_refine_ls_number_parameters     213
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1095
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.133
_refine_ls_shift/su_max          0.006
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.66748(4) 0.72240(3) 0.97229(3) 0.02764(16) Uani 1 1 d . . . . .
O1 O 0.7463(3) 0.6294(2) 0.79400(18) 0.0306(4) Uani 1 1 d . . . . .
O2 O 0.7726(4) 0.4242(3) 0.8612(2) 0.0474(6) Uani 1 1 d . . . . .
N1 N 0.7111(3) 0.6034(2) 0.5403(2) 0.0265(5) Uani 1 1 d . . . . .
H1 H 0.7052 0.6517 0.6207 0.032 Uiso 1 1 calc R U . . .
O5 O 0.6540(3) 0.6254(3) 0.3332(2) 0.0417(5) Uani 1 1 d . . . . .
O3 O 0.8189(3) 0.1611(3) 0.1536(2) 0.0441(6) Uani 1 1 d . . . . .
O4 O 0.9964(3) 0.0393(3) 0.2468(2) 0.0445(6) Uani 1 1 d . . . . .
O13 O 0.7065(3) 0.9593(3) 0.9156(2) 0.0406(5) Uani 1 1 d D . . . .
O12 O 0.5780(4) 0.8246(3) 1.1488(2) 0.0549(7) Uani 1 1 d D . . . .
H12A H 0.4901 0.8651 1.1380 0.082 Uiso 1 1 calc DR U . . .
O11 O 0.4187(3) 0.6376(3) 0.9103(2) 0.0493(6) Uani 1 1 d D . . . .
O14 O 0.9203(4) 0.7513(3) 1.0422(3) 0.0531(6) Uani 1 1 d D . . . .
C7 C 0.7713(4) 0.4913(3) 0.7732(3) 0.0288(6) Uani 1 1 d . . . . .
C1 C 0.8012(3) 0.4083(3) 0.6347(2) 0.0244(5) Uani 1 1 d . . . . .
C6 C 0.7703(3) 0.4614(3) 0.5228(2) 0.0219(5) Uani 1 1 d . . . . .
C9 C 0.6620(4) 0.6765(3) 0.4523(3) 0.0292(6) Uani 1 1 d . . . . .
C10 C 0.6157(4) 0.8311(3) 0.5135(3) 0.0390(7) Uani 1 1 d . . . . .
H10A H 0.6445 0.8948 0.4552 0.058 Uiso 1 1 calc R U . . .
H10B H 0.6824 0.8711 0.5946 0.058 Uiso 1 1 calc R U . . .
H10C H 0.4905 0.8264 0.5298 0.058 Uiso 1 1 calc R U . . .
C5 C 0.8000(3) 0.3732(3) 0.3988(2) 0.0244(5) Uani 1 1 d . . . . .
H5 H 0.7775 0.4072 0.3249 0.029 Uiso 1 1 calc R U . . .
C4 C 0.8631(3) 0.2348(3) 0.3848(3) 0.0257(5) Uani 1 1 d . . . . .
C3 C 0.8945(4) 0.1846(3) 0.4945(3) 0.0301(6) Uani 1 1 d . . . . .
H3 H 0.9383 0.0929 0.4857 0.036 Uiso 1 1 calc R U . . .
C2 C 0.8620(4) 0.2686(3) 0.6171(3) 0.0297(6) Uani 1 1 d . . . . .
H2 H 0.8810 0.2314 0.6897 0.036 Uiso 1 1 calc R U . . .
C8 C 0.8960(4) 0.1382(3) 0.2509(3) 0.0309(6) Uani 1 1 d . . . . .
H13B H 0.803(4) 0.958(4) 0.868(3) 0.046 Uiso 1 1 d D U . . .
H13A H 0.758(5) 1.019(4) 0.988(3) 0.046 Uiso 1 1 d D U . . .
H14B H 0.964(5) 0.836(3) 1.103(3) 0.046 Uiso 1 1 d D U . . .
H11A H 0.360(5) 0.598(4) 0.975(3) 0.046 Uiso 1 1 d D U . . .
H11B H 0.354(4) 0.704(4) 0.883(4) 0.046 Uiso 1 1 d D U . . .
H14A H 0.995(4) 0.748(4) 0.969(3) 0.046 Uiso 1 1 d D U . . .
H12B H 0.662(4) 0.900(3) 1.203(3) 0.046 Uiso 1 1 d D U . . .


_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 O1 1.9903(19) . ?
Cu1 O11 1.996(3) . ?
Cu1 O14 2.011(3) . ?
Cu1 O12 2.027(3) . ?
Cu1 O13 2.398(2) . ?
O1 C7 1.281(4) . ?
O2 C7 1.236(4) . ?
N1 C9 1.348(4) . ?
N1 C6 1.407(3) . ?
N1 H1 0.8600 . ?
O5 C9 1.227(4) . ?
O3 C8 1.251(4) . ?
O4 C8 1.247(4) . ?
O13 H13B 0.883(19) . ?
O13 H13A 0.884(19) . ?
O12 H12A 0.8200 . ?
O12 H12B 0.958(19) . ?
O11 H11A 0.944(19) . ?
O11 H11B 0.922(19) . ?
O14 H14B 0.909(19) . ?
O14 H14A 0.957(19) . ?
C7 C1 1.505(4) . ?
C1 C2 1.391(4) . ?
C1 C6 1.412(4) . ?
C6 C5 1.396(4) . ?
C9 C10 1.502(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C5 C4 1.393(4) . ?
C5 H5 0.9300 . ?
C4 C3 1.376(4) . ?
C4 C8 1.513(4) . ?
C3 C2 1.375(4) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?

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 Cu1 O11 87.93(10) . . ?
O1 Cu1 O14 90.25(10) . . ?
O11 Cu1 O14 164.27(12) . . ?
O1 Cu1 O12 176.48(9) . . ?
O11 Cu1 O12 90.37(11) . . ?
O14 Cu1 O12 92.21(11) . . ?
O1 Cu1 O13 87.95(8) . . ?
O11 Cu1 O13 104.06(10) . . ?
O14 Cu1 O13 91.48(10) . . ?
O12 Cu1 O13 89.48(10) . . ?
C7 O1 Cu1 115.61(17) . . ?
C9 N1 C6 130.9(2) . . ?
C9 N1 H1 114.6 . . ?
C6 N1 H1 114.6 . . ?
Cu1 O13 H13B 106(2) . . ?
Cu1 O13 H13A 102(3) . . ?
H13B O13 H13A 96(3) . . ?
Cu1 O12 H12A 109.5 . . ?
Cu1 O12 H12B 116(2) . . ?
H12A O12 H12B 107.0 . . ?
Cu1 O11 H11A 110(2) . . ?
Cu1 O11 H11B 114(2) . . ?
H11A O11 H11B 112(3) . . ?
Cu1 O14 H14B 121(2) . . ?
Cu1 O14 H14A 107(2) . . ?
H14B O14 H14A 106(3) . . ?
O2 C7 O1 123.1(3) . . ?
O2 C7 C1 119.1(3) . . ?
O1 C7 C1 117.9(2) . . ?
C2 C1 C6 118.3(2) . . ?
C2 C1 C7 117.0(2) . . ?
C6 C1 C7 124.7(2) . . ?
C5 C6 N1 121.9(2) . . ?
C5 C6 C1 119.6(2) . . ?
N1 C6 C1 118.5(2) . . ?
O5 C9 N1 125.0(3) . . ?
O5 C9 C10 121.6(3) . . ?
N1 C9 C10 113.5(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 C8 119.5(2) . . ?
C5 C4 C8 121.1(2) . . ?
C2 C3 C4 120.7(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C2 C1 121.4(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
O4 C8 O3 125.0(3) . . ?
O4 C8 C4 116.8(3) . . ?
O3 C8 C4 118.2(2) . . ?

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
Cu1 O1 C7 O2 -10.2(4) . . . . ?
Cu1 O1 C7 C1 170.11(18) . . . . ?
O2 C7 C1 C2 -11.8(4) . . . . ?
O1 C7 C1 C2 167.9(2) . . . . ?
O2 C7 C1 C6 167.5(3) . . . . ?
O1 C7 C1 C6 -12.8(4) . . . . ?
C9 N1 C6 C5 4.8(4) . . . . ?
C9 N1 C6 C1 -175.6(3) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
C7 C1 C6 C5 -178.9(2) . . . . ?
C2 C1 C6 N1 -179.2(2) . . . . ?
C7 C1 C6 N1 1.6(4) . . . . ?
C6 N1 C9 O5 3.0(5) . . . . ?
C6 N1 C9 C10 -177.2(3) . . . . ?
N1 C6 C5 C4 178.3(2) . . . . ?
C1 C6 C5 C4 -1.2(4) . . . . ?
C6 C5 C4 C3 0.6(4) . . . . ?
C6 C5 C4 C8 -179.9(2) . . . . ?
C5 C4 C3 C2 0.9(4) . . . . ?
C8 C4 C3 C2 -178.6(3) . . . . ?
C4 C3 C2 C1 -1.8(4) . . . . ?
C6 C1 C2 C3 1.1(4) . . . . ?
C7 C1 C2 C3 -179.5(3) . . . . ?
C3 C4 C8 O4 -20.0(4) . . . . ?
C5 C4 C8 O4 160.6(3) . . . . ?
C3 C4 C8 O3 158.7(3) . . . . ?
C5 C4 C8 O3 -20.8(4) . . . . ?

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
N1 H1 O1 0.86 1.91 2.634(3) 140.3 .
O12 H12A O13 0.82 2.48 3.274(4) 162.6 2_677
C5 H5 O5 0.93 2.30 2.919(3) 123.2 .
O13 H13B O4 0.883(19) 1.948(19) 2.829(3) 175(4) 2_766
O13 H13A O3 0.884(19) 1.93(2) 2.800(3) 168(3) 1_566
O14 H14B O4 0.909(19) 2.10(2) 2.989(3) 166(3) 1_566
O11 H11A O2 0.944(19) 2.04(2) 2.954(3) 163(3) 2_667
O11 H11B O3 0.922(19) 2.01(2) 2.919(4) 169(3) 2_666
O14 H14A O3 0.957(19) 2.15(2) 3.047(4) 156(3) 2_766

_refine_diff_density_max         0.675
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.119

_shelxl_version_number           2014-1

_database_code_depnum_ccdc_archive 'CCDC 1005776'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_H2L1

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H25 N3 O7'
_chemical_formula_weight         383.40

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8968(15)
_cell_length_b                   8.8683(18)
_cell_length_c                   16.015(3)
_cell_angle_alpha                99.775(7)
_cell_angle_beta                 98.719(7)
_cell_angle_gamma                111.790(7)
_cell_volume                     997.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2369
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      22.37

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.98
_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_measurement_device_type  'Bruker APEX-II PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14662
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.552
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3652
_reflns_number_gt                1863
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1699P)²+0.0761P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3652
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1473
_refine_ls_R_factor_gt           0.0832
_refine_ls_wR_factor_ref         0.2831
_refine_ls_wR_factor_gt          0.2266
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.001
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.4885(5) 0.9688(4) 0.2377(2) 0.0640(9) Uani 1 1 d . . . . .
C3 C 0.3232(5) 0.8866(5) 0.1738(2) 0.0724(10) Uani 1 1 d . . . . .
H3 H 0.2403 0.9371 0.1641 0.087 Uiso 1 1 calc R U . . .
C4 C 0.2837(5) 0.7289(5) 0.1251(2) 0.0700(10) Uani 1 1 d . . . . .
H4 H 0.1716 0.6732 0.0829 0.084 Uiso 1 1 calc R U . . .
C5 C 0.4040(5) 0.6503(4) 0.1364(2) 0.0615(9) Uani 1 1 d . . . . .
C6 C 0.3534(5) 0.4799(4) 0.0806(2) 0.0656(9) Uani 1 1 d . . . . .
C7 C 0.5760(5) 0.7352(4) 0.2018(2) 0.0622(9) Uani 1 1 d . . . . .
C8 C 0.6132(5) 0.8939(4) 0.2510(2) 0.0662(9) Uani 1 1 d . . . . .
H8 H 0.7242 0.9511 0.2937 0.079 Uiso 1 1 calc R U . . .
C9 C 0.8630(5) 0.7127(4) 0.2745(2) 0.0692(10) Uani 1 1 d . . . . .
C10 C 0.9556(5) 0.5923(5) 0.2701(3) 0.0818(11) Uani 1 1 d . . . . .
H10A H 0.9842 0.5744 0.2134 0.098 Uiso 1 1 calc R U . . .
H10B H 0.8678 0.4856 0.2754 0.098 Uiso 1 1 calc R U . . .
C11 C 1.1338(6) 0.6504(6) 0.3397(3) 0.0981(14) Uani 1 1 d . . . . .
H11A H 1.2240 0.7533 0.3333 0.147 Uiso 1 1 calc R U . . .
H11B H 1.1837 0.5666 0.3339 0.147 Uiso 1 1 calc R U . . .
H11C H 1.1070 0.6683 0.3962 0.147 Uiso 1 1 calc R U . . .
C13 C 0.6336(7) 0.8182(6) 0.4823(3) 0.1024(14) Uani 1 1 d . . . . .
H13A H 0.5409 0.7770 0.4282 0.154 Uiso 1 1 calc R U . . .
H13B H 0.7260 0.9266 0.4840 0.154 Uiso 1 1 calc R U . . .
H13C H 0.5744 0.8270 0.5299 0.154 Uiso 1 1 calc R U . . .
C12 C 0.8899(7) 0.7606(6) 0.5581(3) 0.1248(19) Uani 1 1 d . . . . .
H12A H 0.9463 0.6817 0.5506 0.187 Uiso 1 1 calc R U . . .
H12B H 0.8574 0.7687 0.6136 0.187 Uiso 1 1 calc R U . . .
H12C H 0.9770 0.8685 0.5557 0.187 Uiso 1 1 calc R U . . .
C14 C 0.6641(5) 0.5559(5) 0.4365(2) 0.0806(12) Uani 1 1 d . . . . .
H14 H 0.7316 0.4905 0.4435 0.097 Uiso 1 1 calc R U . . .
C16 C -0.0043(6) 0.8223(5) 0.8162(3) 0.0932(13) Uani 1 1 d . . . . .
H16A H -0.0968 0.7210 0.8229 0.140 Uiso 1 1 calc R U . . .
H16B H 0.0444 0.7969 0.7667 0.140 Uiso 1 1 calc R U . . .
H16C H -0.0607 0.8991 0.8074 0.140 Uiso 1 1 calc R U . . .
C15 C 0.2587(6) 0.8056(5) 0.9145(3) 0.0900(12) Uani 1 1 d . . . . .
H15A H 0.3502 0.8666 0.9684 0.135 Uiso 1 1 calc R U . . .
H15B H 0.3213 0.7916 0.8687 0.135 Uiso 1 1 calc R U . . .
H15C H 0.1789 0.6976 0.9202 0.135 Uiso 1 1 calc R U . . .
C17 C 0.1814(5) 1.0452(5) 0.9423(2) 0.0751(11) Uani 1 1 d . . . . .
H17 H 0.2813 1.0902 0.9910 0.090 Uiso 1 1 calc R U . . .
C1 C 0.5422(5) 1.1414(5) 0.2932(2) 0.0737(10) Uani 1 1 d . . . . .
N1 N 0.6983(4) 0.6578(3) 0.21485(18) 0.0690(8) Uani 1 1 d . . . . .
H1 H 0.6647 0.5611 0.1801 0.083 Uiso 1 1 calc R U . . .
N2 N 0.7225(4) 0.7048(4) 0.4894(2) 0.0785(9) Uani 1 1 d . . . . .
N3 N 0.1467(4) 0.8973(4) 0.89371(18) 0.0715(8) Uani 1 1 d . . . . .
O1 O 0.6868(4) 1.2112(4) 0.3500(2) 0.1142(12) Uani 1 1 d . . . . .
O2 O 0.4234(4) 1.2059(3) 0.27607(18) 0.0991(10) Uani 1 1 d . . . . .
H2O H 0.4614 1.2996 0.3086 0.149 Uiso 1 1 calc R U . . .
O3 O 0.1921(4) 0.4220(3) 0.02491(18) 0.0878(9) Uani 1 1 d . . . . .
H3O H 0.1649 0.3248 -0.0005 0.132 Uiso 1 1 calc R U . . .
O4 O 0.4504(4) 0.4020(3) 0.08469(17) 0.0846(8) Uani 1 1 d . . . . .
O5 O 0.9309(4) 0.8478(4) 0.3279(2) 0.1057(11) Uani 1 1 d . . . . .
O6 O 0.5149(5) 0.4996(4) 0.3752(2) 0.1098(11) Uani 1 1 d . . . . .
O7 O 0.0905(4) 1.1281(3) 0.92771(17) 0.0886(9) Uani 1 1 d . . . . .


_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
C2 C3 1.384(5) . ?
C2 C8 1.388(5) . ?
C2 C1 1.502(5) . ?
C3 C4 1.376(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(5) . ?
C4 H4 0.9300 . ?
C5 C7 1.431(4) . ?
C5 C6 1.492(5) . ?
C6 O4 1.209(4) . ?
C6 O3 1.303(4) . ?
C7 N1 1.389(4) . ?
C7 C8 1.390(5) . ?
C8 H8 0.9300 . ?
C9 O5 1.220(4) . ?
C9 N1 1.355(4) . ?
C9 C10 1.500(5) . ?
C10 C11 1.510(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 N2 1.434(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C12 N2 1.446(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 O6 1.284(4) . ?
C14 N2 1.313(5) . ?
C14 H14 0.9300 . ?
C16 N3 1.445(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15 N3 1.446(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C17 O7 1.228(4) . ?
C17 N3 1.313(5) . ?
C17 H17 0.9300 . ?
C1 O1 1.218(4) . ?
C1 O2 1.286(4) . ?
N1 H1 0.8600 . ?
O2 H2O 0.8200 . ?
O3 H3O 0.8200 . ?

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
C3 C2 C8 120.2(3) . . ?
C3 C2 C1 122.1(3) . . ?
C8 C2 C1 117.7(3) . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 122.5(3) . . ?
C3 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
C4 C5 C7 118.9(3) . . ?
C4 C5 C6 119.8(3) . . ?
C7 C5 C6 121.4(3) . . ?
O4 C6 O3 122.4(3) . . ?
O4 C6 C5 124.7(3) . . ?
O3 C6 C5 112.9(3) . . ?
N1 C7 C8 122.2(3) . . ?
N1 C7 C5 119.8(3) . . ?
C8 C7 C5 117.9(3) . . ?
C2 C8 C7 121.5(3) . . ?
C2 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
O5 C9 N1 123.5(3) . . ?
O5 C9 C10 122.3(3) . . ?
N1 C9 C10 114.2(3) . . ?
C9 C10 C11 113.9(3) . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O6 C14 N2 120.6(4) . . ?
O6 C14 H14 119.7 . . ?
N2 C14 H14 119.7 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O7 C17 N3 124.4(3) . . ?
O7 C17 H17 117.8 . . ?
N3 C17 H17 117.8 . . ?
O1 C1 O2 124.0(3) . . ?
O1 C1 C2 121.3(4) . . ?
O2 C1 C2 114.7(3) . . ?
C9 N1 C7 129.3(3) . . ?
C9 N1 H1 115.4 . . ?
C7 N1 H1 115.4 . . ?
C14 N2 C13 124.2(3) . . ?
C14 N2 C12 118.2(4) . . ?
C13 N2 C12 117.5(4) . . ?
C17 N3 C16 120.4(3) . . ?
C17 N3 C15 121.8(3) . . ?
C16 N3 C15 117.8(3) . . ?
C1 O2 H2O 109.5 . . ?
C6 O3 H3O 109.5 . . ?

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
N1 H1 O4 0.86 1.98 2.680(3) 138.5 .
O2 H2O O6 0.82 1.77 2.584(4) 173.0 1_565
O3 H3O O7 0.82 1.75 2.560(3) 169.0 1_544
C8 H8 O5 0.93 2.19 2.824(5) 124.2 .
C12 H12C O5 0.96 2.64 3.289(6) 125.1 2_776
C14 H14 O1 0.93 2.54 3.215(5) 130.1 1_545
C17 H17 O4 0.93 2.63 3.289(4) 128.3 1_566

_refine_diff_density_max         0.943
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.063

_shelxl_version_number           2014-1

_database_code_depnum_ccdc_archive 'CCDC 1005777'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_H2L2

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H13 N O6'
_chemical_formula_weight         255.22

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.2402(4)
_cell_length_b                   15.2755(8)
_cell_length_c                   9.6698(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.276(2)
_cell_angle_gamma                90
_cell_volume                     1204.49(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4048
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      23.67

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.116
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.97
_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_measurement_device_type  'Bruker APEX-II PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21464
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.498
_diffrn_reflns_theta_max         25.367
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2214
_reflns_number_gt                1542
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0804P)²+0.3047P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2214
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1419
_refine_ls_wR_factor_gt          0.1254
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.002
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0098(3) 0.60340(14) 0.2375(2) 0.0417(5) Uani 1 1 d . . . . .
C2 C 0.1212(2) 0.56582(13) 0.3585(2) 0.0358(5) Uani 1 1 d . . . . .
C3 C 0.1279(3) 0.47565(14) 0.3748(2) 0.0432(6) Uani 1 1 d . . . . .
H3 H 0.0631 0.4405 0.3105 0.052 Uiso 1 1 calc R U . . .
C4 C 0.2282(3) 0.43697(14) 0.4839(2) 0.0428(6) Uani 1 1 d . . . . .
H4 H 0.2320 0.3763 0.4927 0.051 Uiso 1 1 calc R U . . .
C5 C 0.3237(2) 0.48959(13) 0.5807(2) 0.0357(5) Uani 1 1 d . . . . .
C6 C 0.4351(3) 0.45050(13) 0.7003(2) 0.0394(5) Uani 1 1 d . . . . .
C7 C 0.3206(3) 0.57962(13) 0.5666(2) 0.0364(5) Uani 1 1 d . . . . .
H7 H 0.3862 0.6141 0.6315 0.044 Uiso 1 1 calc R U . . .
C8 C 0.2201(3) 0.61925(13) 0.4560(2) 0.0342(5) Uani 1 1 d . . . . .
C9 C 0.2908(3) 0.77529(13) 0.5127(2) 0.0407(5) Uani 1 1 d . . . . .
C10 C 0.2554(3) 0.86455(15) 0.4535(3) 0.0559(7) Uani 1 1 d . . . . .
H10A H 0.3352 0.9051 0.4983 0.084 Uiso 1 1 calc R U . . .
H10B H 0.1478 0.8824 0.4692 0.084 Uiso 1 1 calc R U . . .
H10C H 0.2604 0.8636 0.3550 0.084 Uiso 1 1 calc R U . . .
C11 C 0.7230(4) 0.68379(18) 0.8965(3) 0.0823(10) Uani 1 1 d . . . . .
H11A H 0.8144 0.7185 0.9379 0.124 Uiso 1 1 calc R U . . .
H11B H 0.6236 0.7071 0.9227 0.124 Uiso 1 1 calc R U . . .
H11C H 0.7167 0.6851 0.7966 0.124 Uiso 1 1 calc R U . . .
N1 N 0.2137(2) 0.71008(11) 0.43565(18) 0.0422(5) Uani 1 1 d . . . . .
H1 H 0.1503 0.7269 0.3620 0.051 Uiso 1 1 calc R U . . .
O1 O -0.0008(2) 0.68062(10) 0.20794(16) 0.0579(5) Uani 1 1 d . . . . .
O2 O -0.0768(2) 0.54389(11) 0.16293(17) 0.0640(6) Uani 1 1 d . . . . .
H2O H -0.1325 0.5672 0.0959 0.096 Uiso 1 1 calc R U . . .
O3 O 0.5198(2) 0.49334(10) 0.78712(17) 0.0600(5) Uani 1 1 d . . . . .
O4 O 0.4308(2) 0.36476(10) 0.70100(17) 0.0580(5) Uani 1 1 d . . . . .
H4O H 0.4944 0.3463 0.7676 0.087 Uiso 1 1 calc R U . . .
O5 O 0.3828(2) 0.76300(10) 0.62277(16) 0.0557(5) Uani 1 1 d . . . . .
O6 O 0.7436(3) 0.59877(12) 0.9427(2) 0.0971(9) Uani 1 1 d . . . . .
H6 H 0.6806 0.5667 0.8925 0.146 Uiso 1 1 calc R U . . .


_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 1.214(3) . ?
C1 O2 1.307(3) . ?
C1 C2 1.494(3) . ?
C2 C3 1.387(3) . ?
C2 C8 1.413(3) . ?
C3 C4 1.376(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9300 . ?
C5 C7 1.382(3) . ?
C5 C6 1.494(3) . ?
C6 O3 1.205(2) . ?
C6 O4 1.310(2) . ?
C7 C8 1.393(3) . ?
C7 H7 0.9300 . ?
C8 N1 1.401(3) . ?
C9 O5 1.229(2) . ?
C9 N1 1.347(3) . ?
C9 C10 1.491(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 O6 1.376(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
N1 H1 0.8600 . ?
O2 H2O 0.8200 . ?
O4 H4O 0.8200 . ?
O6 H6 0.8200 . ?

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 O2 122.0(2) . . ?
O1 C1 C2 124.99(19) . . ?
O2 C1 C2 112.97(18) . . ?
C3 C2 C8 119.20(18) . . ?
C3 C2 C1 118.74(18) . . ?
C8 C2 C1 122.05(18) . . ?
C4 C3 C2 121.57(19) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 119.17(19) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C7 C5 C4 120.59(19) . . ?
C7 C5 C6 118.35(18) . . ?
C4 C5 C6 121.05(18) . . ?
O3 C6 O4 123.57(19) . . ?
O3 C6 C5 123.51(19) . . ?
O4 C6 C5 112.92(18) . . ?
C5 C7 C8 120.57(19) . . ?
C5 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 N1 122.96(18) . . ?
C7 C8 C2 118.89(18) . . ?
N1 C8 C2 118.15(17) . . ?
O5 C9 N1 123.32(19) . . ?
O5 C9 C10 122.29(19) . . ?
N1 C9 C10 114.39(18) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O6 C11 H11A 109.5 . . ?
O6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 N1 C8 130.48(18) . . ?
C9 N1 H1 114.8 . . ?
C8 N1 H1 114.8 . . ?
C1 O2 H2O 109.5 . . ?
C6 O4 H4O 109.5 . . ?
C11 O6 H6 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 C1 C2 C3 -176.1(2) . . . . ?
O2 C1 C2 C3 3.2(3) . . . . ?
O1 C1 C2 C8 3.6(4) . . . . ?
O2 C1 C2 C8 -177.1(2) . . . . ?
C8 C2 C3 C4 0.2(3) . . . . ?
C1 C2 C3 C4 179.9(2) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C7 -1.2(3) . . . . ?
C3 C4 C5 C6 -179.7(2) . . . . ?
C7 C5 C6 O3 1.7(3) . . . . ?
C4 C5 C6 O3 -179.7(2) . . . . ?
C7 C5 C6 O4 -178.4(2) . . . . ?
C4 C5 C6 O4 0.2(3) . . . . ?
C4 C5 C7 C8 0.8(3) . . . . ?
C6 C5 C7 C8 179.35(19) . . . . ?
C5 C7 C8 N1 -179.1(2) . . . . ?
C5 C7 C8 C2 0.0(3) . . . . ?
C3 C2 C8 C7 -0.5(3) . . . . ?
C1 C2 C8 C7 179.77(19) . . . . ?
C3 C2 C8 N1 178.7(2) . . . . ?
C1 C2 C8 N1 -1.0(3) . . . . ?
O5 C9 N1 C8 -1.7(4) . . . . ?
C10 C9 N1 C8 178.3(2) . . . . ?
C7 C8 N1 C9 -2.5(4) . . . . ?
C2 C8 N1 C9 178.4(2) . . . . ?

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
O6 H6 O3 0.82 1.91 2.731(2) 174.7 .
O4 H4O O5 0.82 1.86 2.632(2) 156.5 2_646
O2 H2O O6 0.82 1.74 2.554(2) 170.3 1_454
N1 H1 O1 0.86 1.93 2.656(2) 140.9 .
C10 H10A O3 0.96 2.61 3.501(3) 153.6 2_656
C7 H7 O5 0.93 2.28 2.885(3) 122.5 .

_refine_diff_density_max         0.248
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.052

_shelxl_version_number           2014-1

_database_code_depnum_ccdc_archive 'CCDC 1005778'
