# 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 1825038'
_audit_update_record             
;
2018-02-21 deposited with the CCDC.
2018-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H11 N O3'
_chemical_formula_sum            'C11 H11 N O3'
_chemical_formula_weight         205.21

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                   8.0084(3)
_cell_length_b                   8.1626(3)
_cell_length_c                   8.5962(3)
_cell_angle_alpha                63.646(2)
_cell_angle_beta                 69.490(2)
_cell_angle_gamma                73.138(2)
_cell_volume                     465.51(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3584
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      28.21

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.463
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9788
_exptl_absorpt_correction_T_max  0.9872
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            7164
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.737
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1801
_reflns_number_gt                1440
_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, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0505P)²+0.0413P] 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_number_reflns         1801
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.1044
_refine_ls_wR_factor_gt          0.0976
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
C1 C 0.86503(15) 0.01284(17) 0.36835(16) 0.0301(3) Uani 1 1 d . . . . .
C2 C 0.89510(17) 0.16881(18) 0.21490(17) 0.0353(3) Uani 1 1 d . . . . .
H2 H 0.9970 0.1615 0.1220 0.042 Uiso 1 1 calc R U . . .
C3 C 0.77854(18) 0.33935(19) 0.19187(18) 0.0379(3) Uani 1 1 d . . . . .
C4 C 0.60293(17) 0.20242(17) 0.49369(17) 0.0333(3) Uani 1 1 d . . . . .
C5 C 0.45710(18) 0.2325(2) 0.62886(19) 0.0407(3) Uani 1 1 d . . . . .
H5 H 0.3872 0.3492 0.6103 0.049 Uiso 1 1 calc R U . . .
C6 C 0.41689(18) 0.0882(2) 0.79027(19) 0.0435(4) Uani 1 1 d . . . . .
H6 H 0.3183 0.1069 0.8816 0.052 Uiso 1 1 calc R U . . .
C7 C 0.52140(18) -0.0847(2) 0.81885(19) 0.0425(3) Uani 1 1 d . . . . .
H7 H 0.4931 -0.1819 0.9290 0.051 Uiso 1 1 calc R U . . .
C8 C 0.66723(17) -0.11319(18) 0.68456(18) 0.0365(3) Uani 1 1 d . . . . .
H8 H 0.7375 -0.2299 0.7049 0.044 Uiso 1 1 calc R U . . .
C9 C 0.71137(15) 0.03094(17) 0.51766(17) 0.0300(3) Uani 1 1 d . . . . .
C10 C 1.11684(16) -0.18624(18) 0.24164(18) 0.0357(3) Uani 1 1 d . . . . .
H10A H 1.2160 -0.1282 0.2228 0.043 Uiso 1 1 calc R U . . .
H10B H 1.0786 -0.1307 0.1313 0.043 Uiso 1 1 calc R U . . .
C11 C 1.18056(18) -0.38982(19) 0.28490(19) 0.0433(4) Uani 1 1 d . . . . .
H11A H 1.2914 -0.4072 0.1959 0.052 Uiso 1 1 calc R U . . .
H11B H 1.2074 -0.4469 0.4011 0.052 Uiso 1 1 calc R U . . .
N1 N 0.96767(13) -0.15264(14) 0.38562(14) 0.0341(3) Uani 1 1 d . . . . .
H1 H 0.9442 -0.2438 0.4871 0.041 Uiso 1 1 calc R U . . .
O1 O 0.78928(15) 0.48098(13) 0.05625(14) 0.0542(3) Uani 1 1 d . . . . .
O2 O 0.63432(12) 0.35290(12) 0.33409(12) 0.0420(3) Uani 1 1 d . . . . .
O3 O 1.05094(13) -0.47982(13) 0.28832(13) 0.0490(3) Uani 1 1 d . . . . .
H3 H 1.0667 -0.4766 0.1875 0.074 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
C1 N1 1.3362(15) . ?
C1 C2 1.3723(18) . ?
C1 C9 1.4627(16) . ?
C2 C3 1.4069(18) . ?
C2 H2 0.9300 . ?
C3 O1 1.2222(16) . ?
C3 O2 1.3774(15) . ?
C4 O2 1.3768(16) . ?
C4 C5 1.3821(18) . ?
C4 C9 1.3856(18) . ?
C5 C6 1.368(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.380(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.3736(18) . ?
C7 H7 0.9300 . ?
C8 C9 1.3981(18) . ?
C8 H8 0.9300 . ?
C10 N1 1.4524(15) . ?
C10 C11 1.5009(18) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O3 1.4213(17) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
N1 H1 0.8600 . ?
O3 H3 0.8200 . ?

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
N1 C1 C2 123.08(11) . . ?
N1 C1 C9 119.33(11) . . ?
C2 C1 C9 117.58(11) . . ?
C1 C2 C3 122.91(12) . . ?
C1 C2 H2 118.5 . . ?
C3 C2 H2 118.5 . . ?
O1 C3 O2 114.66(12) . . ?
O1 C3 C2 127.00(13) . . ?
O2 C3 C2 118.34(12) . . ?
O2 C4 C5 116.09(11) . . ?
O2 C4 C9 122.00(11) . . ?
C5 C4 C9 121.92(12) . . ?
C6 C5 C4 119.13(13) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C7 120.58(12) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 119.99(13) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 120.87(12) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C4 C9 C8 117.50(12) . . ?
C4 C9 C1 118.16(11) . . ?
C8 C9 C1 124.34(11) . . ?
N1 C10 C11 111.27(11) . . ?
N1 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
N1 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O3 C11 C10 112.63(11) . . ?
O3 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
O3 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C1 N1 C10 123.28(11) . . ?
C1 N1 H1 118.4 . . ?
C10 N1 H1 118.4 . . ?
C4 O2 C3 120.87(10) . . ?
C11 O3 H3 109.5 . . ?

_refine_diff_density_max         0.154
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.050

_shelxl_version_number           2014-3

