# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_mx3426
_audit_block_doi                 10.5517/cc1jlgh2
_database_code_depnum_ccdc_archive 'CCDC 1417924'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C5RA16097A 2015
_audit_update_record             
;
2016-04-12 deposited with the CCDC.
2016-04-13 downloaded from the CCDC.
;
_audit_creation_date             2014-12-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '4(H2 O), C16 H15 N O3'
_chemical_formula_sum            'C16 H23 N O7'
_chemical_formula_weight         341.35
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.3846(13)
_cell_length_b                   16.788(4)
_cell_length_c                   7.9738(16)
_cell_angle_alpha                90
_cell_angle_beta                 92.052(4)
_cell_angle_gamma                90
_cell_volume                     854.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3346
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4755
_cell_measurement_theta_min      1.2129
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9558
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         2.556
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             2029
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0010
_diffrn_orient_matrix_UB_12      0.1501
_diffrn_orient_matrix_UB_13      -0.0450
_diffrn_orient_matrix_UB_21      0.0087
_diffrn_orient_matrix_UB_22      -0.0169
_diffrn_orient_matrix_UB_23      -0.0565
_diffrn_orient_matrix_UB_31      -0.1241
_diffrn_orient_matrix_UB_32      -0.0017
_diffrn_orient_matrix_UB_33      -0.0187
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_full    0.946
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                3680
_reflns_number_total             3768
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution    
;
'SHELXS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1627 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.4(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3768
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0552P)²+0.0811P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0926
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C12(H12), C15(H15)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O7 O 0.7323(3) 0.30660(12) 0.5722(3) 0.0488(5) Uani 1 1 d . . . . .
O6 O 0.4593(3) 0.30182(13) 0.8329(3) 0.0486(5) Uani 1 1 d . . . . .
O5 O 0.1592(3) 0.27750(10) 0.5809(2) 0.0366(4) Uani 1 1 d . . . . .
O1 O 0.4088(2) 0.36786(8) 0.36620(19) 0.0281(3) Uani 1 1 d . . . . .
O2 O 0.0493(2) 0.36259(9) 0.1999(2) 0.0334(3) Uani 1 1 d . . . . .
O3 O -0.0749(3) 0.65664(11) 0.0157(2) 0.0432(4) Uani 1 1 d . . . . .
N1 N 1.3339(2) 0.53701(10) 0.7658(2) 0.0261(4) Uani 1 1 d . . . . .
C1 C 1.5302(3) 0.52542(15) 0.8670(3) 0.0337(5) Uani 1 1 d . . . . .
H1A H 1.6105 0.5738 0.8676 0.050 Uiso 1 1 calc GR . . . .
H1B H 1.6103 0.4833 0.8192 0.050 Uiso 1 1 calc GR . . . .
H1C H 1.4972 0.5117 0.9799 0.050 Uiso 1 1 calc GR . . . .
C2 C 1.2752(3) 0.60990(13) 0.7119(3) 0.0298(4) Uani 1 1 d . . . . .
H2 H 1.3600 0.6536 0.7371 0.036 Uiso 1 1 calc R . . . .
C3 C 1.0911(3) 0.62035(12) 0.6199(3) 0.0283(4) Uani 1 1 d . . . . .
H3 H 1.0524 0.6712 0.5844 0.034 Uiso 1 1 calc R . . . .
C4 C 0.9608(3) 0.55551(11) 0.5788(2) 0.0228(4) Uani 1 1 d . . . . .
C5 C 1.0290(3) 0.48061(12) 0.6368(3) 0.0266(4) Uani 1 1 d . . . . .
H5 H 0.9485 0.4357 0.6121 0.032 Uiso 1 1 calc R . . . .
C6 C 1.2126(3) 0.47301(13) 0.7293(3) 0.0278(4) Uani 1 1 d . . . . .
H6 H 1.2545 0.4230 0.7676 0.033 Uiso 1 1 calc R . . . .
C7 C 0.7670(3) 0.56736(12) 0.4790(2) 0.0242(4) Uani 1 1 d . . . . .
H7 H 0.7303 0.6188 0.4459 0.029 Uiso 1 1 calc R . . . .
C8 C 0.6402(3) 0.50710(11) 0.4336(2) 0.0233(4) Uani 1 1 d . . . . .
H8 H 0.6834 0.4569 0.4702 0.028 Uiso 1 1 calc R . . . .
C9 C 0.4443(3) 0.50904(11) 0.3349(2) 0.0216(4) Uani 1 1 d . . . . .
C10 C 0.3561(3) 0.57918(11) 0.2682(3) 0.0244(4) Uani 1 1 d . . . . .
H10 H 0.4244 0.6274 0.2872 0.029 Uiso 1 1 calc R . . . .
C11 C 0.1689(3) 0.57795(12) 0.1742(3) 0.0249(4) Uani 1 1 d . . . . .
C12 C 0.0615(3) 0.50505(12) 0.1457(3) 0.0253(4) Uani 1 1 d . . . . .
H12 H -0.0631 0.5042 0.0816 0.030 Uiso 1 1 calc R . . . .
C13 C 0.1413(3) 0.43594(11) 0.2124(2) 0.0241(4) Uani 1 1 d . . . . .
C14 C 0.3389(3) 0.43441(11) 0.3084(2) 0.0218(4) Uani 1 1 d . . . . .
C15 C 0.0841(3) 0.65153(13) 0.1053(3) 0.0333(5) Uani 1 1 d . . . . .
H15 H 0.1560 0.6984 0.1311 0.040 Uiso 1 1 calc R . . . .
C16 C -0.1413(3) 0.35674(14) 0.1017(3) 0.0367(5) Uani 1 1 d . . . . .
H16A H -0.2447 0.3912 0.1477 0.055 Uiso 1 1 calc GR . . . .
H16B H -0.1908 0.3028 0.1031 0.055 Uiso 1 1 calc GR . . . .
H16C H -0.1168 0.3723 -0.0117 0.055 Uiso 1 1 calc GR . . . .
O4 O 0.6015(2) 0.73905(10) 0.8497(2) 0.0354(4) Uani 1 1 d . . . . .
H6A H 0.449(6) 0.276(2) 0.933(5) 0.063(10) Uiso 1 1 d . . . . .
H6B H 0.362(6) 0.292(2) 0.776(5) 0.062(11) Uiso 1 1 d . . . . .
H7A H 0.646(5) 0.318(2) 0.498(4) 0.052(9) Uiso 1 1 d . . . . .
H7B H 0.655(7) 0.301(3) 0.663(5) 0.077(12) Uiso 1 1 d . . . . .
H5A H 0.216(5) 0.3038(19) 0.507(4) 0.044(8) Uiso 1 1 d . . . . .
H5B H 0.033(6) 0.285(2) 0.569(4) 0.054(9) Uiso 1 1 d . . . . .
H4A H 0.725(6) 0.716(2) 0.878(4) 0.056(9) Uiso 1 1 d . . . . .
H4B H 0.621(5) 0.784(2) 0.780(4) 0.046(8) Uiso 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
O1 C14 1.283(2) . ?
O2 C13 1.366(2) . ?
O2 C16 1.427(2) . ?
O3 C15 1.224(3) . ?
N1 C1 1.479(2) . ?
N1 C2 1.346(3) . ?
N1 C6 1.350(3) . ?
C2 C3 1.374(3) . ?
C3 C4 1.401(3) . ?
C4 C5 1.404(3) . ?
C4 C7 1.460(2) . ?
C5 C6 1.369(3) . ?
C7 C8 1.338(3) . ?
C8 C9 1.454(2) . ?
C9 C10 1.402(3) . ?
C9 C14 1.434(2) . ?
C10 C11 1.388(3) . ?
C11 C12 1.417(3) . ?
C11 C15 1.449(3) . ?
C12 C13 1.367(3) . ?
C13 C14 1.453(2) . ?

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
C13 O2 C16 117.24(16) . . ?
C2 N1 C1 120.99(17) . . ?
C2 N1 C6 120.23(16) . . ?
C6 N1 C1 118.78(18) . . ?
N1 C2 C3 120.65(17) . . ?
C2 C3 C4 120.98(18) . . ?
C3 C4 C5 116.38(16) . . ?
C3 C4 C7 120.37(17) . . ?
C5 C4 C7 123.24(16) . . ?
C6 C5 C4 120.70(18) . . ?
N1 C6 C5 121.06(18) . . ?
C8 C7 C4 122.50(17) . . ?
C7 C8 C9 129.07(18) . . ?
C10 C9 C8 123.37(16) . . ?
C10 C9 C14 119.87(16) . . ?
C14 C9 C8 116.76(16) . . ?
C11 C10 C9 121.24(17) . . ?
C10 C11 C12 120.12(17) . . ?
C10 C11 C15 119.65(18) . . ?
C12 C11 C15 120.23(17) . . ?
C13 C12 C11 119.95(16) . . ?
O2 C13 C12 125.71(16) . . ?
O2 C13 C14 112.65(15) . . ?
C12 C13 C14 121.64(16) . . ?
O1 C14 C9 123.54(15) . . ?
O1 C14 C13 119.31(16) . . ?
C9 C14 C13 117.15(15) . . ?
O3 C15 C11 124.9(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 H6A O4 0.92(4) 1.88(4) 2.781(3) 169(3) 2_647
O6 H6B O5 0.77(4) 2.01(4) 2.757(3) 164(4) .
O7 H7A O1 0.81(4) 2.00(4) 2.789(2) 164(3) .
O7 H7B O6 0.89(4) 1.88(4) 2.761(3) 170(4) .
O5 H5A O1 0.83(4) 2.01(4) 2.823(2) 167(3) .
O5 H5B O7 0.82(4) 1.95(4) 2.767(3) 172(3) 1_455
O4 H4A O3 0.90(4) 1.93(4) 2.782(2) 157(3) 1_656
O4 H4B O1 0.94(3) 1.84(3) 2.763(2) 166(3) 2_656
O4 H4B O2 0.94(3) 2.49(3) 3.081(2) 121(2) 2_656

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 C13 C14 O1 1.7(3) . . . . ?
O2 C13 C14 C9 -177.51(16) . . . . ?
N1 C2 C3 C4 -0.5(3) . . . . ?
C1 N1 C2 C3 -179.1(2) . . . . ?
C1 N1 C6 C5 179.67(19) . . . . ?
C2 N1 C6 C5 0.2(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C2 C3 C4 C7 -179.19(19) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C3 C4 C7 C8 178.5(2) . . . . ?
C4 C5 C6 N1 -0.7(3) . . . . ?
C4 C7 C8 C9 -179.74(19) . . . . ?
C5 C4 C7 C8 -0.8(3) . . . . ?
C6 N1 C2 C3 0.3(3) . . . . ?
C7 C4 C5 C6 179.74(19) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C7 C8 C9 C14 -178.79(19) . . . . ?
C8 C9 C10 C11 179.77(18) . . . . ?
C8 C9 C14 O1 -0.2(3) . . . . ?
C8 C9 C14 C13 179.01(16) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C9 C10 C11 C15 -179.14(19) . . . . ?
C10 C9 C14 O1 -179.57(19) . . . . ?
C10 C9 C14 C13 -0.4(3) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
C10 C11 C15 O3 177.1(2) . . . . ?
C11 C12 C13 O2 177.23(19) . . . . ?
C11 C12 C13 C14 -2.0(3) . . . . ?
C12 C11 C15 O3 -2.8(3) . . . . ?
C12 C13 C14 O1 -178.90(18) . . . . ?
C12 C13 C14 C9 1.8(3) . . . . ?
C14 C9 C10 C11 -0.9(3) . . . . ?
C15 C11 C12 C13 -179.37(19) . . . . ?
C16 O2 C13 C12 3.4(3) . . . . ?
C16 O2 C13 C14 -177.32(17) . . . . ?

