# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_mo_2016378_0ma
_database_code_depnum_ccdc_archive 'CCDC 1558694'

_audit_update_record             
;
2017-06-27 deposited with the CCDC.
2017-07-31 downloaded from the CCDC.
;
_audit_creation_date             2016-07-19
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5203)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13 N O4'
_chemical_formula_sum            'C12 H13 N O4'
_chemical_formula_weight         235.23
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.9045(4)
_cell_length_b                   10.4027(10)
_cell_length_c                   12.0076(10)
_cell_angle_alpha                83.328(4)
_cell_angle_beta                 80.762(6)
_cell_angle_gamma                89.239(6)
_cell_volume                     600.58(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3298
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.23
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0746 before and 0.0511 after correction.
The Ratio of minimum to maximum transmission is 0.8920.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_special_details           ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9835
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.567
_diffrn_reflns_theta_min         1.730
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1846
_reflns_number_total             2736
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2736
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0812
_refine_ls_restrained_S_all      1.072
_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)+(0.1194P)²+0.6842P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2603
_refine_ls_wR_factor_ref         0.2765
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.3, Nqual =  -1, Ralpha = 0.043
;
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 -0.3954(5) 0.7593(3) 0.0093(3) 0.0729(9) Uani 1 1 d . . . . .
O2 O -0.0091(5) 0.8689(3) -0.0691(2) 0.0596(7) Uani 1 1 d . . . . .
O3 O 0.5430(8) 0.8853(3) 0.3312(3) 0.0954(12) Uani 1 1 d . . . . .
O4 O 0.6530(6) 0.7522(3) 0.4748(2) 0.0703(8) Uani 1 1 d . . . . .
N1 N 0.0174(5) 0.7134(3) 0.0687(2) 0.0465(7) Uani 1 1 d . . . . .
H1 H 0.1831 0.7424 0.0627 0.056 Uiso 1 1 calc R . . . .
C1 C -0.0118(8) 0.4657(4) 0.3178(4) 0.0595(9) Uani 1 1 d . . . . .
H1A H 0.0648 0.4492 0.3840 0.071 Uiso 1 1 calc R . . . .
C2 C -0.1890(9) 0.3753(4) 0.2915(4) 0.0678(11) Uani 1 1 d . . . . .
H2 H -0.2327 0.2995 0.3401 0.081 Uiso 1 1 calc R . . . .
C3 C -0.3008(8) 0.3988(4) 0.1920(4) 0.0616(10) Uani 1 1 d . . . . .
H3 H -0.4213 0.3387 0.1744 0.074 Uiso 1 1 calc R . . . .
C4 C -0.2359(7) 0.5090(4) 0.1197(3) 0.0514(9) Uani 1 1 d . . . . .
H4 H -0.3101 0.5231 0.0528 0.062 Uiso 1 1 calc R . . . .
C5 C -0.0572(6) 0.6015(3) 0.1460(3) 0.0424(7) Uani 1 1 d . . . . .
C6 C 0.0545(6) 0.5810(3) 0.2471(3) 0.0451(8) Uani 1 1 d . . . . .
C7 C 0.2291(7) 0.6797(3) 0.2771(3) 0.0495(8) Uani 1 1 d . . . . .
H7 H 0.2391 0.7589 0.2319 0.059 Uiso 1 1 calc R . . . .
C8 C 0.3759(7) 0.6694(4) 0.3618(3) 0.0521(8) Uani 1 1 d . . . . .
H8 H 0.3811 0.5909 0.4072 0.062 Uiso 1 1 calc R . . . .
C9 C 0.5286(7) 0.7807(4) 0.3836(3) 0.0537(9) Uani 1 1 d . . . . .
C10 C 0.8014(11) 0.8568(5) 0.5077(5) 0.0877(16) Uani 1 1 d . . . . .
H10A H 0.8886 0.9096 0.4409 0.132 Uiso 1 1 calc GR . . . .
H10B H 0.9394 0.8220 0.5509 0.132 Uiso 1 1 calc GR . . . .
H10C H 0.6748 0.9085 0.5531 0.132 Uiso 1 1 calc GR . . . .
C11 C -0.1516(6) 0.7781(3) 0.0036(3) 0.0469(8) Uani 1 1 d . . . . .
C12 C -0.1616(11) 0.9469(5) -0.1443(4) 0.0795(13) Uani 1 1 d . . . . .
H12A H -0.0372 1.0046 -0.1963 0.119 Uiso 1 1 calc GR . . . .
H12B H -0.2971 0.9964 -0.1008 0.119 Uiso 1 1 calc GR . . . .
H12C H -0.2523 0.8920 -0.1861 0.119 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
O1 C11 1.204(4) . ?
O2 C11 1.331(4) . ?
O2 C12 1.437(5) . ?
O3 C9 1.189(5) . ?
O4 C9 1.340(5) . ?
O4 C10 1.443(5) . ?
N1 H1 0.8600 . ?
N1 C5 1.415(4) . ?
N1 C11 1.350(4) . ?
C1 H1A 0.9300 . ?
C1 C2 1.385(6) . ?
C1 C6 1.397(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.364(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.405(4) . ?
C5 C6 1.404(5) . ?
C6 C7 1.458(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.331(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.459(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C11 O2 C12 116.5(3) . . ?
C9 O4 C10 116.1(4) . . ?
C5 N1 H1 117.5 . . ?
C11 N1 H1 117.5 . . ?
C11 N1 C5 125.0(3) . . ?
C2 C1 H1A 119.3 . . ?
C2 C1 C6 121.5(4) . . ?
C6 C1 H1A 119.3 . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.4(4) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 N1 119.9(3) . . ?
C6 C5 N1 119.9(3) . . ?
C6 C5 C4 120.1(3) . . ?
C1 C6 C5 118.0(3) . . ?
C1 C6 C7 121.8(3) . . ?
C5 C6 C7 120.2(3) . . ?
C6 C7 H7 116.3 . . ?
C8 C7 C6 127.4(4) . . ?
C8 C7 H7 116.3 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.2(4) . . ?
C9 C8 H8 119.9 . . ?
O3 C9 O4 122.2(4) . . ?
O3 C9 C8 126.7(4) . . ?
O4 C9 C8 111.1(3) . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 O2 123.9(3) . . ?
O1 C11 N1 126.3(3) . . ?
O2 C11 N1 109.8(3) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
N1 C5 C6 C1 -176.3(3) . . . . ?
N1 C5 C6 C7 5.0(4) . . . . ?
C1 C2 C3 C4 0.6(6) . . . . ?
C1 C6 C7 C8 10.0(6) . . . . ?
C2 C1 C6 C5 -2.0(5) . . . . ?
C2 C1 C6 C7 176.7(4) . . . . ?
C2 C3 C4 C5 -0.9(6) . . . . ?
C3 C4 C5 N1 177.7(3) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 C1 1.7(5) . . . . ?
C4 C5 C6 C7 -177.0(3) . . . . ?
C5 N1 C11 O1 8.0(6) . . . . ?
C5 N1 C11 O2 -172.5(3) . . . . ?
C5 C6 C7 C8 -171.4(3) . . . . ?
C6 C1 C2 C3 0.8(6) . . . . ?
C6 C7 C8 C9 -176.7(3) . . . . ?
C7 C8 C9 O3 -1.3(6) . . . . ?
C7 C8 C9 O4 177.4(3) . . . . ?
C10 O4 C9 O3 1.3(6) . . . . ?
C10 O4 C9 C8 -177.5(4) . . . . ?
C11 N1 C5 C4 36.2(5) . . . . ?
C11 N1 C5 C6 -145.8(3) . . . . ?
C12 O2 C11 O1 -0.3(6) . . . . ?
C12 O2 C11 N1 -179.7(3) . . . . ?

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