# 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_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



