# 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

 
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



