# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1829970'
_audit_update_record             
;
2018-03-15 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H14 N2 O4'
_chemical_formula_weight         226.23

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.2976(5)
_cell_length_b                   13.2046(13)
_cell_length_c                   15.2907(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1069.63(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    980
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10121
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.038
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_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             1885
_reflns_number_gt                1802
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.670
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    
;    
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0398P)²+0.1986P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1.2(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1885
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0689
_refine_ls_wR_factor_gt          0.0671
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_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
O1 O 0.5238(3) 0.72295(11) 0.18958(11) 0.0411(4) Uani 1 1 d . . . . .
O2 O 0.1824(3) 0.65155(10) 0.24689(10) 0.0338(4) Uani 1 1 d . . . . .
H2 H 0.238520 0.600879 0.222731 0.051 Uiso 1 1 calc R U . . .
C1 C 0.3281(4) 0.72950(14) 0.22918(12) 0.0226(4) Uani 1 1 d . . . . .
C2 C 0.2167(4) 0.82677(13) 0.26168(12) 0.0234(4) Uani 1 1 d . . . . .
H2C H 0.156536 0.816690 0.320959 0.028 Uiso 1 1 calc R U . . .
H2D H 0.072129 0.843828 0.225642 0.028 Uiso 1 1 calc R U . . .
C3 C 0.3993(4) 0.91502(13) 0.26101(12) 0.0235(4) Uani 1 1 d . . . . .
H3A H 0.479822 0.918226 0.204111 0.028 Uiso 1 1 calc R U . . .
H3B H 0.304596 0.977229 0.268939 0.028 Uiso 1 1 calc R U . . .
C4 C 0.6013(3) 0.90942(13) 0.33035(11) 0.0202(4) Uani 1 1 d . . . . .
O3 O 0.7637(3) 0.98025(9) 0.33235(9) 0.0240(3) Uani 1 1 d . . . . .
O4 O 0.6012(3) 0.83725(10) 0.38244(9) 0.0287(3) Uani 1 1 d . . . . .
N1 N 0.1118(3) 0.98004(11) 0.46310(10) 0.0209(3) Uani 1 1 d . . . . .
H1 H -0.001447 0.977237 0.422874 0.025 Uiso 1 1 calc R U . . .
N2 N -0.0471(3) 0.83137(11) 0.51863(10) 0.0269(4) Uani 1 1 d . . . . .
H2A H -0.158174 0.831002 0.477594 0.032 Uiso 1 1 calc R U . . .
H2B H -0.044497 0.783376 0.556633 0.032 Uiso 1 1 calc R U . . .
C9 C 0.1193(3) 0.90565(13) 0.52327(12) 0.0208(4) Uani 1 1 d . . . . .
C10 C 0.6355(4) 1.15714(15) 0.52614(14) 0.0315(5) Uani 1 1 d . . . . .
H10A H 0.625970 1.192476 0.471372 0.047 Uiso 1 1 calc R U . . .
H10B H 0.804594 1.133130 0.535050 0.047 Uiso 1 1 calc R U . . .
H10C H 0.590111 1.202272 0.572789 0.047 Uiso 1 1 calc R U . . .
C6 C 0.4571(4) 1.06896(13) 0.52492(12) 0.0237(4) Uani 1 1 d . . . . .
C7 C 0.4696(4) 0.99161(14) 0.58838(12) 0.0256(4) Uani 1 1 d . . . . .
H7 H 0.592895 0.995254 0.631561 0.031 Uiso 1 1 calc R U . . .
C8 C 0.3073(4) 0.91196(14) 0.58844(12) 0.0235(4) Uani 1 1 d . . . . .
H8 H 0.319997 0.861984 0.631069 0.028 Uiso 1 1 calc R U . . .
C5 C 0.2754(4) 1.05946(13) 0.46312(12) 0.0225(4) Uani 1 1 d . . . . .
H5 H 0.262257 1.108421 0.419641 0.027 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
O1 C1 1.204(2) . ?
O2 C1 1.315(2) . ?
O2 H2 0.8200 . ?
C1 C2 1.498(2) . ?
C2 C3 1.514(2) . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C3 C4 1.508(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O4 1.242(2) . ?
C4 O3 1.271(2) . ?
N1 C9 1.346(2) . ?
N1 C5 1.361(2) . ?
N1 H1 0.8600 . ?
N2 C9 1.321(2) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C9 C8 1.411(3) . ?
C10 C6 1.500(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C6 C5 1.354(3) . ?
C6 C7 1.410(3) . ?
C7 C8 1.359(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C5 H5 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
C1 O2 H2 109.5 . . ?
O1 C1 O2 123.56(17) . . ?
O1 C1 C2 124.59(17) . . ?
O2 C1 C2 111.82(16) . . ?
C1 C2 C3 113.94(15) . . ?
C1 C2 H2C 108.8 . . ?
C3 C2 H2C 108.8 . . ?
C1 C2 H2D 108.8 . . ?
C3 C2 H2D 108.8 . . ?
H2C C2 H2D 107.7 . . ?
C4 C3 C2 114.24(15) . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
O4 C4 O3 123.31(17) . . ?
O4 C4 C3 119.24(16) . . ?
O3 C4 C3 117.46(15) . . ?
C9 N1 C5 122.91(16) . . ?
C9 N1 H1 118.5 . . ?
C5 N1 H1 118.5 . . ?
C9 N2 H2A 120.0 . . ?
C9 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N2 C9 N1 119.04(16) . . ?
N2 C9 C8 123.57(16) . . ?
N1 C9 C8 117.40(16) . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C6 C7 116.51(17) . . ?
C5 C6 C10 121.89(17) . . ?
C7 C6 C10 121.60(17) . . ?
C8 C7 C6 122.10(17) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C9 119.46(17) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C6 C5 N1 121.61(16) . . ?
C6 C5 H5 119.2 . . ?
N1 C5 H5 119.2 . . ?

_refine_diff_density_max         0.137
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1829971'
_audit_update_record             
;
2018-03-15 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H14 N2 O4'
_chemical_formula_weight         226.23

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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.932(2)
_cell_length_b                   20.575(3)
_cell_length_c                   10.644(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.413(2)
_cell_angle_gamma                90
_cell_volume                     1071.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1250
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12174
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.765
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             1845
_reflns_number_gt                1785
_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       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    
;    
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_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)+(0.0354P)²+0.3144P] 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     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.066(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1845
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0693
_refine_ls_wR_factor_gt          0.0687
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
O4 O 0.40639(14) 0.17498(3) 0.83821(6) 0.01778(19) Uani 1 1 d . . . . .
O3 O 0.42823(13) 0.23136(3) 1.01830(6) 0.01618(18) Uani 1 1 d . . . . .
C4 C 0.32753(18) 0.18721(4) 0.94220(8) 0.0126(2) Uani 1 1 d . . . . .
C3 C 0.09774(19) 0.14702(5) 0.98501(9) 0.0139(2) Uani 1 1 d . . . . .
H3A H -0.045959 0.176050 1.004621 0.017 Uiso 1 1 calc R U . . .
H3B H 0.167037 0.124128 1.062185 0.017 Uiso 1 1 calc R U . . .
C2 C -0.02387(19) 0.09783(5) 0.88688(9) 0.0146(2) Uani 1 1 d . . . . .
H2D H -0.104593 0.120774 0.811610 0.018 Uiso 1 1 calc R U . . .
H2C H 0.121236 0.070404 0.863176 0.018 Uiso 1 1 calc R U . . .
C1 C -0.23695(19) 0.05600(4) 0.93421(9) 0.0135(2) Uani 1 1 d . . . . .
O2 O -0.34878(14) 0.01334(3) 0.84983(6) 0.01904(19) Uani 1 1 d . . . . .
H2 H -0.458219 -0.009304 0.881883 0.029 Uiso 1 1 calc R U . . .
O1 O -0.30020(14) 0.05964(3) 1.04142(6) 0.01767(19) Uani 1 1 d . . . . .
N1 N -0.18543(16) 0.31373(4) 0.95976(7) 0.0140(2) Uani 1 1 d . . . . .
H1 H -0.307212 0.287312 0.980588 0.017 Uiso 1 1 calc R U . . .
N2 N -0.22656(17) 0.26542(4) 0.76259(8) 0.0164(2) Uani 1 1 d . . . . .
H2A H -0.345754 0.239209 0.786478 0.020 Uiso 1 1 calc R U . . .
H2B H -0.181854 0.262573 0.687313 0.020 Uiso 1 1 calc R U . . .
C9 C -0.11192(18) 0.31014(4) 0.84168(8) 0.0132(2) Uani 1 1 d . . . . .
C8 C 0.08451(19) 0.35533(5) 0.80810(9) 0.0143(2) Uani 1 1 d . . . . .
H8 H 0.138318 0.353858 0.727567 0.017 Uiso 1 1 calc R U . . .
C7 C 0.19517(19) 0.40098(5) 0.89315(9) 0.0155(2) Uani 1 1 d . . . . .
C5 C -0.07267(19) 0.35782(5) 1.04650(9) 0.0158(2) Uani 1 1 d . . . . .
H5 H -0.124757 0.357881 1.127413 0.019 Uiso 1 1 calc R U . . .
C6 C 0.1146(2) 0.40171(5) 1.01688(9) 0.0167(2) Uani 1 1 d . . . . .
H6 H 0.189308 0.431872 1.076635 0.020 Uiso 1 1 calc R U . . .
C10 C 0.3971(2) 0.44997(5) 0.85683(9) 0.0182(2) Uani 1 1 d . . . . .
H10A H 0.441797 0.440080 0.773792 0.027 Uiso 1 1 calc R U . . .
H10B H 0.559991 0.448489 0.916794 0.027 Uiso 1 1 calc R U . . .
H10C H 0.318464 0.492662 0.856694 0.027 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
O4 C4 1.2453(12) . ?
O3 C4 1.2744(11) . ?
C4 C3 1.5196(13) . ?
C3 C2 1.5209(13) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C2 C1 1.4952(13) . ?
C2 H2D 0.9700 . ?
C2 H2C 0.9700 . ?
C1 O1 1.2235(12) . ?
C1 O2 1.3242(12) . ?
O2 H2 0.8200 . ?
N1 C9 1.3543(12) . ?
N1 C5 1.3609(13) . ?
N1 H1 0.8600 . ?
N2 C9 1.3237(12) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C9 C8 1.4213(13) . ?
C8 C7 1.3682(14) . ?
C8 H8 0.9300 . ?
C7 C6 1.4239(14) . ?
C7 C10 1.5021(13) . ?
C5 C6 1.3577(14) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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
O4 C4 O3 124.62(9) . . ?
O4 C4 C3 119.15(8) . . ?
O3 C4 C3 116.23(8) . . ?
C4 C3 C2 113.54(8) . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C1 C2 C3 112.56(8) . . ?
C1 C2 H2D 109.1 . . ?
C3 C2 H2D 109.1 . . ?
C1 C2 H2C 109.1 . . ?
C3 C2 H2C 109.1 . . ?
H2D C2 H2C 107.8 . . ?
O1 C1 O2 122.63(9) . . ?
O1 C1 C2 123.64(8) . . ?
O2 C1 C2 113.73(8) . . ?
C1 O2 H2 109.5 . . ?
C9 N1 C5 122.07(8) . . ?
C9 N1 H1 119.0 . . ?
C5 N1 H1 119.0 . . ?
C9 N2 H2A 120.0 . . ?
C9 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N2 C9 N1 118.98(8) . . ?
N2 C9 C8 122.95(9) . . ?
N1 C9 C8 118.06(8) . . ?
C7 C8 C9 120.62(9) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C7 C6 118.95(9) . . ?
C8 C7 C10 120.76(9) . . ?
C6 C7 C10 120.28(9) . . ?
C6 C5 N1 121.11(9) . . ?
C6 C5 H5 119.4 . . ?
N1 C5 H5 119.4 . . ?
C5 C6 C7 119.15(9) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
O4 C4 C3 C2 -3.99(12) . . . . ?
O3 C4 C3 C2 176.75(8) . . . . ?
C4 C3 C2 C1 176.32(7) . . . . ?
C3 C2 C1 O1 -2.13(13) . . . . ?
C3 C2 C1 O2 179.11(8) . . . . ?
C5 N1 C9 N2 178.95(8) . . . . ?
C5 N1 C9 C8 -1.59(13) . . . . ?
N2 C9 C8 C7 179.45(9) . . . . ?
N1 C9 C8 C7 0.01(13) . . . . ?
C9 C8 C7 C6 1.25(14) . . . . ?
C9 C8 C7 C10 -178.32(8) . . . . ?
C9 N1 C5 C6 1.88(14) . . . . ?
N1 C5 C6 C7 -0.53(14) . . . . ?
C8 C7 C6 C5 -1.00(14) . . . . ?
C10 C7 C6 C5 178.58(9) . . . . ?

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1829972'
_audit_update_record             
;
2018-03-15 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H24 N4 O8'
_chemical_formula_weight         424.41

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                   10.144(2)
_cell_length_b                   5.166(2)
_cell_length_c                   19.037(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.248(3)
_cell_angle_gamma                90
_cell_volume                     966.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1450
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.116
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8423
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.071
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_full        24.991
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             1674
_reflns_number_gt                1591
_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       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    
;    
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_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)+(0.0356P)²+0.3748P] 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     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.201(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1674
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0776
_refine_ls_wR_factor_gt          0.0762
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_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
O1 O 0.49470(8) -0.07174(16) 0.12863(4) 0.0216(2) Uani 1 1 d . . . . .
N1 N 0.74718(9) 0.63045(19) 0.27927(5) 0.0194(2) Uani 1 1 d . . . . .
H1 H 0.720481 0.646247 0.318575 0.023 Uiso 1 1 calc R U . . .
O4 O 0.78151(9) 0.40129(17) -0.01372(4) 0.0263(2) Uani 1 1 d . . . . .
H4 H 0.747123 0.514334 -0.042706 0.039 Uiso 1 1 calc R U . . .
O2 O 0.32710(8) 0.21362(16) 0.09487(4) 0.0234(2) Uani 1 1 d . . . . .
O3 O 0.89647(9) 0.31529(18) -0.09706(5) 0.0310(3) Uani 1 1 d . . . . .
N2 N 0.61032(10) 0.2683(2) 0.25175(5) 0.0239(3) Uani 1 1 d . . . . .
H2A H 0.586773 0.287243 0.291864 0.029 Uiso 1 1 calc R U . . .
H2B H 0.577783 0.142333 0.223198 0.029 Uiso 1 1 calc R U . . .
C9 C 0.69707(11) 0.4339(2) 0.23387(6) 0.0185(3) Uani 1 1 d . . . . .
C8 C 0.74079(11) 0.4129(2) 0.16901(6) 0.0210(3) Uani 1 1 d . . . . .
H8 H 0.707370 0.281130 0.136170 0.025 Uiso 1 1 calc R U . . .
C1 C 0.42345(11) 0.0753(2) 0.08252(6) 0.0169(3) Uani 1 1 d . . . . .
C5 C 0.83825(11) 0.8049(2) 0.26545(6) 0.0214(3) Uani 1 1 d . . . . .
H5 H 0.869959 0.937404 0.298346 0.026 Uiso 1 1 calc R U . . .
C4 C 0.95035(12) 0.0795(2) 0.01494(6) 0.0210(3) Uani 1 1 d . . . . .
H4A H 0.885485 -0.035873 0.028655 0.025 Uiso 1 1 calc R U . . .
H4B H 0.999702 0.168778 0.058291 0.025 Uiso 1 1 calc R U . . .
C7 C 0.83204(12) 0.5865(2) 0.15484(6) 0.0222(3) Uani 1 1 d . . . . .
H7 H 0.860799 0.572313 0.112231 0.027 Uiso 1 1 calc R U . . .
C2 C 0.45176(12) 0.1009(2) 0.00833(6) 0.0217(3) Uani 1 1 d . . . . .
H2C H 0.489672 0.271187 0.004478 0.026 Uiso 1 1 calc R U . . .
H2D H 0.366201 0.089658 -0.028084 0.026 Uiso 1 1 calc R U . . .
C3 C 0.87425(11) 0.2755(2) -0.03839(6) 0.0185(3) Uani 1 1 d . . . . .
C6 C 0.88319(12) 0.7871(2) 0.20404(6) 0.0231(3) Uani 1 1 d . . . . .
H6 H 0.946253 0.904558 0.194726 0.028 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
O1 C1 1.2479(14) . ?
N1 C9 1.3493(15) . ?
N1 C5 1.3618(15) . ?
N1 H1 0.8600 . ?
O4 C3 1.3211(14) . ?
O4 H4 0.8200 . ?
O2 C1 1.2784(14) . ?
O3 C3 1.2102(14) . ?
N2 C9 1.3301(16) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C9 C8 1.4151(16) . ?
C8 C7 1.3625(17) . ?
C8 H8 0.9300 . ?
C1 C2 1.5148(16) . ?
C5 C6 1.3586(17) . ?
C5 H5 0.9300 . ?
C4 C3 1.5054(16) . ?
C4 C4 1.515(2) 3_755 ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C7 C6 1.4073(18) . ?
C7 H7 0.9300 . ?
C2 C2 1.516(2) 3_655 ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C6 H6 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
C9 N1 C5 122.75(10) . . ?
C9 N1 H1 118.6 . . ?
C5 N1 H1 118.6 . . ?
C3 O4 H4 109.5 . . ?
C9 N2 H2A 120.0 . . ?
C9 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N2 C9 N1 119.25(10) . . ?
N2 C9 C8 122.91(11) . . ?
N1 C9 C8 117.83(10) . . ?
C7 C8 C9 119.77(11) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
O1 C1 O2 123.20(10) . . ?
O1 C1 C2 119.95(10) . . ?
O2 C1 C2 116.83(10) . . ?
C6 C5 N1 120.57(11) . . ?
C6 C5 H5 119.7 . . ?
N1 C5 H5 119.7 . . ?
C3 C4 C4 112.92(12) . 3_755 ?
C3 C4 H4A 109.0 . . ?
C4 C4 H4A 109.0 3_755 . ?
C3 C4 H4B 109.0 . . ?
C4 C4 H4B 109.0 3_755 . ?
H4A C4 H4B 107.8 . . ?
C8 C7 C6 120.66(11) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C1 C2 C2 114.53(12) . 3_655 ?
C1 C2 H2C 108.6 . . ?
C2 C2 H2C 108.6 3_655 . ?
C1 C2 H2D 108.6 . . ?
C2 C2 H2D 108.6 3_655 . ?
H2C C2 H2D 107.6 . . ?
O3 C3 O4 123.72(10) . . ?
O3 C3 C4 123.76(10) . . ?
O4 C3 C4 112.51(9) . . ?
C5 C6 C7 118.41(11) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?

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
C5 N1 C9 N2 178.75(10) . . . . ?
C5 N1 C9 C8 -0.81(16) . . . . ?
N2 C9 C8 C7 -178.68(11) . . . . ?
N1 C9 C8 C7 0.87(16) . . . . ?
C9 N1 C5 C6 -0.04(17) . . . . ?
C9 C8 C7 C6 -0.11(17) . . . . ?
O1 C1 C2 C2 12.15(19) . . . 3_655 ?
O2 C1 C2 C2 -169.30(12) . . . 3_655 ?
C4 C4 C3 O3 -4.93(19) 3_755 . . . ?
C4 C4 C3 O4 175.76(12) 3_755 . . . ?
N1 C5 C6 C7 0.82(17) . . . . ?
C8 C7 C6 C5 -0.73(18) . . . . ?

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.038

