# 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_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



