# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_X17067
_database_code_depnum_ccdc_archive 'CCDC 1577981'
_audit_update_record             
;
2017-10-03 deposited with the CCDC.
2017-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 N2 O4'
_chemical_formula_weight         278.30

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                   6.746(3)
_cell_length_b                   7.246(3)
_cell_length_c                   7.434(3)
_cell_angle_alpha                77.801(7)
_cell_angle_beta                 83.650(8)
_cell_angle_gamma                88.409(7)
_cell_volume                     353.0(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8839
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      33.28

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             148
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.113
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.290833
_exptl_absorpt_correction_T_max  0.746552
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            2771
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.820
_diffrn_reflns_theta_max         33.642
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2771
_reflns_number_gt                2101
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _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 v2011.4.0 (Bruker-AXS, 2015)'
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component 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)+(0.1369P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2771
_refine_ls_number_parameters     134
_refine_ls_number_restraints     163
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.2064
_refine_ls_wR_factor_gt          0.1933
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.048
_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
O1 O 0.51580(14) 0.65815(12) 0.40051(13) 0.0276(3) Uani 1 1 d D U . . .
H1 H 0.512(7) 0.546(4) 0.464(6) 0.041 Uiso 0.5 1 d D U P . .
O2 O 0.81011(18) 0.56329(14) 0.28345(17) 0.0426(3) Uani 1 1 d . U . . .
C1 C 0.68145(19) 0.68289(15) 0.29706(16) 0.0216(3) Uani 1 1 d . U . . .
C2 C 0.71171(17) 0.87538(15) 0.18979(15) 0.0204(2) Uani 1 1 d . U . . .
C3 C 0.73738(17) 1.03452(15) 0.10549(15) 0.0199(2) Uani 1 1 d . U . . .
C4 C 0.76728(19) 1.22780(16) 0.00416(18) 0.0243(3) Uani 1 1 d . U . . .
H4A H 0.8984 1.2389 -0.0684 0.036 Uiso 1 1 calc R U . . .
H4B H 0.7604 1.3124 0.0916 0.036 Uiso 1 1 calc R U . . .
H4C H 0.6632 1.2627 -0.0791 0.036 Uiso 1 1 calc R U . . .
N1S N 1.1289(3) 0.1594(3) 0.3627(3) 0.0195(4) Uani 0.5 1 d . U P A -1
N2S N 0.9257(3) -0.0345(2) 0.5485(2) 0.0173(4) Uani 0.5 1 d . U P A -1
C1S C 1.2161(18) 0.3325(16) 0.2424(16) 0.0300(18) Uani 0.5 1 d . U P A -1
H1SA H 1.3588 0.3365 0.2553 0.045 Uiso 0.5 1 calc R U P A -1
H1SB H 1.1496 0.4432 0.2784 0.045 Uiso 0.5 1 calc R U P A -1
H1SC H 1.1978 0.3330 0.1133 0.045 Uiso 0.5 1 calc R U P A -1
C2S C 1.2181(4) -0.0157(3) 0.3877(3) 0.0217(4) Uani 0.5 1 d . U P A -1
H2S H 1.3466 -0.0449 0.3344 0.026 Uiso 0.5 1 calc R U P A -1
C3S C 1.0883(10) -0.1399(11) 0.5032(9) 0.0211(9) Uani 0.5 1 d . U P A -1
H3S H 1.1068 -0.2720 0.5438 0.025 Uiso 0.5 1 calc R U P A -1
C4S C 0.9512(10) 0.1420(11) 0.4615(9) 0.0202(9) Uani 0.5 1 d . U P A -1
H4S H 0.8576 0.2414 0.4680 0.024 Uiso 0.5 1 calc R U P A -1
C5S C 0.7396(4) -0.1050(3) 0.6649(3) 0.0221(4) Uani 0.5 1 d . U P A -1
H5SA H 0.6294 -0.0959 0.5859 0.027 Uiso 0.5 1 calc R U P A -1
H5SB H 0.7048 -0.0247 0.7564 0.027 Uiso 0.5 1 calc R U P A -1
C6S C 0.7619(16) -0.3064(15) 0.7649(16) 0.0254(14) Uani 0.5 1 d . U P A -1
H6SA H 0.7866 -0.3874 0.6746 0.038 Uiso 0.5 1 calc R U P A -1
H6SB H 0.6392 -0.3465 0.8459 0.038 Uiso 0.5 1 calc R U P A -1
H6SC H 0.8742 -0.3165 0.8395 0.038 Uiso 0.5 1 calc R U P A -1


_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 1.2787(15) . ?
O1 H1 0.846(18) . ?
O2 C1 1.2209(16) . ?
C1 C2 1.4604(15) . ?
C2 C3 1.1976(15) . ?
C3 C4 1.4512(16) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N1S C4S 1.329(6) . ?
N1S C2S 1.374(3) . ?
N1S C1S 1.473(11) . ?
N2S C4S 1.312(7) . ?
N2S C3S 1.371(6) . ?
N2S C5S 1.481(3) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
C2S C3S 1.366(7) . ?
C2S H2S 0.9500 . ?
C3S H3S 0.9500 . ?
C4S H4S 0.9500 . ?
C5S C6S 1.503(11) . ?
C5S H5SA 0.9900 . ?
C5S H5SB 0.9900 . ?
C6S H6SA 0.9800 . ?
C6S H6SB 0.9800 . ?
C6S H6SC 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
C1 O1 H1 109(3) . . ?
O2 C1 O1 126.13(11) . . ?
O2 C1 C2 119.76(11) . . ?
O1 C1 C2 114.11(10) . . ?
C3 C2 C1 178.48(12) . . ?
C2 C3 C4 179.58(14) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C4S N1S C2S 107.9(4) . . ?
C4S N1S C1S 127.0(6) . . ?
C2S N1S C1S 125.0(5) . . ?
C4S N2S C3S 109.7(3) . . ?
C4S N2S C5S 123.3(3) . . ?
C3S N2S C5S 126.9(3) . . ?
N1S C1S H1SA 109.5 . . ?
N1S C1S H1SB 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
N1S C1S H1SC 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
C3S C2S N1S 107.5(3) . . ?
C3S C2S H2S 126.2 . . ?
N1S C2S H2S 126.2 . . ?
C2S C3S N2S 105.7(5) . . ?
C2S C3S H3S 127.1 . . ?
N2S C3S H3S 127.1 . . ?
N2S C4S N1S 109.1(5) . . ?
N2S C4S H4S 125.4 . . ?
N1S C4S H4S 125.4 . . ?
N2S C5S C6S 111.4(5) . . ?
N2S C5S H5SA 109.3 . . ?
C6S C5S H5SA 109.3 . . ?
N2S C5S H5SB 109.3 . . ?
C6S C5S H5SB 109.3 . . ?
H5SA C5S H5SB 108.0 . . ?
C5S C6S H6SA 109.5 . . ?
C5S C6S H6SB 109.5 . . ?
H6SA C6S H6SB 109.5 . . ?
C5S C6S H6SC 109.5 . . ?
H6SA C6S H6SC 109.5 . . ?
H6SB C6S H6SC 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
O1 H1 O1 0.846(18) 1.609(18) 2.4519(18) 174(5) 2_666

_refine_diff_density_max         0.450
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.075

