# 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 2018

####################################################################### 
# 
# 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. 
# 
#######################################################################

data_sad
_database_code_depnum_ccdc_archive 'CCDC 1587933'
_audit_update_record             
;
2017-11-27 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;
_audit_creation_date             2017-11-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H19 N O9'
_chemical_formula_sum            'C14 H19 N O9'
_chemical_formula_weight         345.30
_chemical_absolute_configuration syn
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   8.8584(18)
_cell_length_b                   7.6373(15)
_cell_length_c                   12.517(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.91(3)
_cell_angle_gamma                90
_cell_volume                     822.0(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    19394
_cell_measurement_temperature    200
_cell_measurement_theta_max      68.000
_cell_measurement_theta_min      3.638
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.017
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0805 before and 0.0612 after correction.
The Ratio of minimum to maximum transmission is 0.8732.
The λ/2 correction factor is 0.0000.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19394
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.975
_diffrn_reflns_theta_min         3.638
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            KappaCCD
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker kappaCCD'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_source_target            Mo
_diffrn_source_type              'fine-focus sealed tube'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.834
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                2838
_reflns_number_total             2885
_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       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    ?
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details 
;
 Flack x determined using 1239 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2885
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0564
_refine_ls_restrained_S_all      1.100
_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)+(0.0977P)²+1.2107P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1798
_refine_ls_wR_factor_ref         0.1812
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C1(H1A,H1B)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C21(H21A,H21B,
 H21C)
;
_atom_sites_solution_hydrogens   geom
_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
O10 O 0.7246(4) 0.1804(5) 0.2079(3) 0.0287(8) Uani 1 1 d . . . . .
O11 O 0.3688(4) 0.3538(5) 0.2616(3) 0.0297(9) Uani 1 1 d . . . . .
O12 O 0.7602(4) 0.2739(5) 0.4299(3) 0.0311(9) Uani 1 1 d . . . . .
O8 O 0.7362(5) 0.7421(6) 0.2903(4) 0.0407(10) Uani 1 1 d . . . . .
O9 O 0.7189(5) 0.4132(5) 0.0346(3) 0.0335(9) Uani 1 1 d . . . . .
N7 N 0.6778(5) 0.5855(6) 0.2894(4) 0.0279(10) Uani 1 1 d . . . . .
O18 O 0.5904(5) 0.0317(7) 0.0592(4) 0.0442(11) Uani 1 1 d . . . . .
O17 O 0.7834(6) 0.6094(7) -0.0782(4) 0.0465(12) Uani 1 1 d . . . . .
O19 O 0.2555(5) 0.1489(6) 0.3456(4) 0.0396(10) Uani 1 1 d . . . . .
C15 C 0.2456(6) 0.2785(8) 0.2912(4) 0.0293(12) Uani 1 1 d . . . . .
C13 C 0.7421(7) 0.4666(8) -0.0626(5) 0.0337(13) Uani 1 1 d . . . . .
O20 O 0.6754(6) 0.0450(8) 0.5109(5) 0.0585(15) Uani 1 1 d . . . . .
C4 C 0.5174(6) 0.2661(7) 0.2946(4) 0.0262(11) Uani 1 1 d . . . . .
H4 H 0.5029 0.1375 0.3035 0.031 Uiso 1 1 calc R . . . .
C5 C 0.6041(6) 0.3477(8) 0.4029(4) 0.0305(12) Uani 1 1 d . . . . .
H5 H 0.5495 0.3230 0.4625 0.037 Uiso 1 1 calc R . . . .
C2 C 0.6652(6) 0.4809(7) 0.2065(4) 0.0263(11) Uani 1 1 d . . . . .
C3 C 0.5965(6) 0.3015(7) 0.2016(4) 0.0261(11) Uani 1 1 d . . . . .
H3 H 0.5193 0.2859 0.1295 0.031 Uiso 1 1 calc R . . . .
C16 C 0.7774(7) 0.1171(9) 0.4790(5) 0.0378(14) Uani 1 1 d . . . . .
C14 C 0.7117(7) 0.0643(8) 0.1241(5) 0.0319(12) Uani 1 1 d . . . . .
C6 C 0.6228(6) 0.5419(8) 0.3892(4) 0.0297(12) Uani 1 1 d . . . . .
H6A H 0.5217 0.6003 0.3848 0.036 Uiso 1 1 calc R . . . .
H6B H 0.6981 0.5880 0.4549 0.036 Uiso 1 1 calc R . . . .
C1 C 0.7271(7) 0.5524(8) 0.1141(5) 0.0299(12) Uani 1 1 d . . . . .
H1A H 0.6640 0.6537 0.0798 0.036 Uiso 1 1 calc R . . . .
H1B H 0.8361 0.5915 0.1418 0.036 Uiso 1 1 calc R . . . .
C23 C 0.1020(7) 0.3813(9) 0.2449(5) 0.0396(14) Uani 1 1 d . . . . .
H23A H 0.1187 0.5037 0.2684 0.059 Uiso 1 1 calc GR . . . .
H23B H 0.0153 0.3327 0.2714 0.059 Uiso 1 1 calc GR . . . .
H23C H 0.0776 0.3754 0.1643 0.059 Uiso 1 1 calc GR . . . .
C22 C 0.8648(8) -0.0157(9) 0.1245(6) 0.0423(15) Uani 1 1 d . . . . .
H22A H 0.9237 0.0632 0.0879 0.063 Uiso 1 1 calc GR . . . .
H22B H 0.8486 -0.1278 0.0853 0.063 Uiso 1 1 calc GR . . . .
H22C H 0.9230 -0.0352 0.2007 0.063 Uiso 1 1 calc GR . . . .
C24 C 0.9377(8) 0.0459(12) 0.4894(7) 0.0513(17) Uani 1 1 d . . . . .
H24A H 0.9678 0.0616 0.4196 0.077 Uiso 1 1 calc GR . . . .
H24B H 0.9392 -0.0790 0.5075 0.077 Uiso 1 1 calc GR . . . .
H24C H 1.0112 0.1086 0.5480 0.077 Uiso 1 1 calc GR . . . .
C21 C 0.7071(12) 0.3197(11) -0.1449(6) 0.059(2) Uani 1 1 d . . . . .
H21A H 0.7730 0.2188 -0.1167 0.088 Uiso 1 1 calc GR . . . .
H21B H 0.7279 0.3583 -0.2146 0.088 Uiso 1 1 calc GR . . . .
H21C H 0.5975 0.2862 -0.1569 0.088 Uiso 1 1 calc GR . . . .


_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
O10 C3 1.451(6) . ?
O10 C14 1.358(7) . ?
O11 C15 1.362(7) . ?
O11 C4 1.446(6) . ?
O12 C5 1.456(6) . ?
O12 C16 1.338(8) . ?
O8 N7 1.302(6) . ?
O9 C13 1.345(7) . ?
O9 C1 1.446(7) . ?
N7 C2 1.293(7) . ?
N7 C6 1.484(7) . ?
O18 C14 1.207(7) . ?
O17 C13 1.182(8) . ?
O19 C15 1.193(8) . ?
C15 C23 1.489(8) . ?
C13 C21 1.504(10) . ?
O20 C16 1.205(8) . ?
C4 H4 1.0000 . ?
C4 C5 1.521(8) . ?
C4 C3 1.521(7) . ?
C5 H5 1.0000 . ?
C5 C6 1.507(9) . ?
C2 C3 1.494(8) . ?
C2 C1 1.498(7) . ?
C3 H3 1.0000 . ?
C16 C24 1.497(9) . ?
C14 C22 1.486(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C14 O10 C3 117.0(4) . . ?
C15 O11 C4 117.4(4) . . ?
C16 O12 C5 116.8(4) . . ?
C13 O9 C1 114.0(5) . . ?
O8 N7 C6 114.1(5) . . ?
C2 N7 O8 122.2(5) . . ?
C2 N7 C6 123.6(5) . . ?
O11 C15 C23 109.6(5) . . ?
O19 C15 O11 123.5(5) . . ?
O19 C15 C23 126.8(5) . . ?
O9 C13 C21 110.0(5) . . ?
O17 C13 O9 123.3(6) . . ?
O17 C13 C21 126.6(6) . . ?
O11 C4 H4 110.8 . . ?
O11 C4 C5 107.2(4) . . ?
O11 C4 C3 104.7(4) . . ?
C5 C4 H4 110.8 . . ?
C5 C4 C3 112.5(4) . . ?
C3 C4 H4 110.8 . . ?
O12 C5 C4 107.3(4) . . ?
O12 C5 H5 110.9 . . ?
O12 C5 C6 106.4(4) . . ?
C4 C5 H5 110.9 . . ?
C6 C5 C4 110.4(4) . . ?
C6 C5 H5 110.9 . . ?
N7 C2 C3 123.8(5) . . ?
N7 C2 C1 114.6(5) . . ?
C3 C2 C1 121.6(5) . . ?
O10 C3 C4 110.1(4) . . ?
O10 C3 C2 106.0(4) . . ?
O10 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
C2 C3 C4 112.9(5) . . ?
C2 C3 H3 109.2 . . ?
O12 C16 C24 111.5(5) . . ?
O20 C16 O12 123.3(6) . . ?
O20 C16 C24 125.2(6) . . ?
O10 C14 C22 111.0(5) . . ?
O18 C14 O10 123.4(5) . . ?
O18 C14 C22 125.6(6) . . ?
N7 C6 C5 112.6(5) . . ?
N7 C6 H6A 109.1 . . ?
N7 C6 H6B 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
O9 C1 C2 107.2(4) . . ?
O9 C1 H1A 110.3 . . ?
O9 C1 H1B 110.3 . . ?
C2 C1 H1A 110.3 . . ?
C2 C1 H1B 110.3 . . ?
H1A C1 H1B 108.5 . . ?
C15 C23 H23A 109.5 . . ?
C15 C23 H23B 109.5 . . ?
C15 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C14 C22 H22A 109.5 . . ?
C14 C22 H22B 109.5 . . ?
C14 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C16 C24 H24A 109.5 . . ?
C16 C24 H24B 109.5 . . ?
C16 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C13 C21 H21A 109.5 . . ?
C13 C21 H21B 109.5 . . ?
C13 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
