# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_soeta01
_database_code_depnum_ccdc_archive 'CCDC 1427940'
_audit_update_record             
;
2015-09-28 deposited with the CCDC.
2015-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ????
_chemical_melting_point          ????
_chemical_formula_moiety         C12H16N2O2
_chemical_formula_sum            'C12 H16 N2 O2'
_chemical_formula_weight         220.27

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/a'
_space_group_name_Hall           '-P 2yab'

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

_cell_length_a                   10.604(2)
_cell_length_b                   10.844(2)
_cell_length_c                   11.111(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.939(5)
_cell_angle_gamma                90
_cell_volume                     1254.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    93
_cell_measurement_reflns_used    4424
_cell_measurement_theta_min      3.498
_cell_measurement_theta_max      25.096

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.800
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7260
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku/MSC Inc., 2006)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      93
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Mercury (2x2 bin mode)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 14.4613
_diffrn_reflns_number            11158
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.498
_diffrn_reflns_theta_max         25.096
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             2195
_reflns_number_gt                1780
_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       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-3
_computing_publication_material  ORTEP-3

_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)+(0.0987P)²+0.1852P] 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         2195
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1622
_refine_ls_wR_factor_gt          0.1495
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 0.05061(14) 0.22609(14) -0.11540(15) 0.0437(4) Uani 1 1 d . . . . .
C2 C -0.01756(16) 0.32196(16) -0.07501(17) 0.0540(5) Uani 1 1 d . . . . .
H1 H -0.0201 0.3299 0.0096 0.065 Uiso 1 1 calc R U . . .
C3 C -0.08223(18) 0.40636(18) -0.1592(2) 0.0646(5) Uani 1 1 d . . . . .
H2 H -0.1288 0.4721 -0.1317 0.078 Uiso 1 1 calc R U . . .
C4 C -0.0790(2) 0.39511(19) -0.2814(2) 0.0698(6) Uani 1 1 d . . . . .
H3 H -0.1253 0.4516 -0.3387 0.084 Uiso 1 1 calc R U . . .
C5 C -0.0087(2) 0.3018(2) -0.32134(18) 0.0714(6) Uani 1 1 d . . . . .
H4 H -0.0056 0.2949 -0.4060 0.086 Uiso 1 1 calc R U . . .
C6 C 0.05680(19) 0.21878(16) -0.23909(16) 0.0572(5) Uani 1 1 d . . . . .
H5 H 0.1067 0.1559 -0.2669 0.069 Uiso 1 1 calc R U . . .
C7 C 0.11601(14) 0.13329(14) -0.02834(14) 0.0422(4) Uani 1 1 d . . . . .
N1 N 0.12667(12) 0.02347(12) -0.06841(12) 0.0465(4) Uani 1 1 d . . . . .
O1 O 0.19587(12) -0.05394(11) 0.02100(11) 0.0564(4) Uani 1 1 d . . . . .
H6 H 0.2059 -0.1230 -0.0101 0.085 Uiso 1 1 calc R U . . .
C8 C 0.17510(14) 0.17330(14) 0.10031(14) 0.0438(4) Uani 1 1 d . . . . .
O2 O 0.26677(12) 0.24467(12) 0.11584(12) 0.0613(4) Uani 1 1 d . . . . .
N2 N 0.12212(12) 0.12728(12) 0.18936(11) 0.0465(4) Uani 1 1 d . . . . .
H7 H 0.0500 0.0859 0.1677 0.056 Uiso 1 1 calc R U . . .
C9 C 0.17374(17) 0.13945(16) 0.32198(15) 0.0539(5) Uani 1 1 d . . . . .
C10 C 0.1839(3) 0.2736(2) 0.3596(2) 0.0852(7) Uani 1 1 d . . . . .
H8 H 0.2447 0.3156 0.3172 0.128 Uiso 1 1 calc R U . . .
H9 H 0.2142 0.2795 0.4484 0.128 Uiso 1 1 calc R U . . .
H10 H 0.0993 0.3127 0.3375 0.128 Uiso 1 1 calc R U . . .
C11 C 0.0803(3) 0.0747(3) 0.3885(2) 0.0943(9) Uani 1 1 d . . . . .
H11 H -0.0050 0.1119 0.3647 0.141 Uiso 1 1 calc R U . . .
H12 H 0.1098 0.0832 0.4771 0.141 Uiso 1 1 calc R U . . .
H13 H 0.0758 -0.0129 0.3665 0.141 Uiso 1 1 calc R U . . .
C12 C 0.3045(3) 0.0770(3) 0.3492(2) 0.0944(8) Uani 1 1 d . . . . .
H14 H 0.2954 -0.0096 0.3239 0.142 Uiso 1 1 calc R U . . .
H15 H 0.3394 0.0816 0.4374 0.142 Uiso 1 1 calc R U . . .
H16 H 0.3629 0.1187 0.3040 0.142 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 C2 1.388(2) . ?
C1 C6 1.390(2) . ?
C1 C7 1.475(2) . ?
C2 C3 1.392(3) . ?
C2 H1 0.9500 . ?
C3 C4 1.371(3) . ?
C3 H2 0.9500 . ?
C4 C5 1.379(3) . ?
C4 H3 0.9500 . ?
C5 C6 1.374(3) . ?
C5 H4 0.9500 . ?
C6 H5 0.9500 . ?
C7 N1 1.284(2) . ?
C7 C8 1.511(2) . ?
N1 O1 1.3976(17) . ?
O1 H6 0.8400 . ?
C8 O2 1.2288(19) . ?
C8 N2 1.325(2) . ?
N2 C9 1.477(2) . ?
N2 H7 0.8800 . ?
C9 C10 1.512(3) . ?
C9 C11 1.516(3) . ?
C9 C12 1.521(3) . ?
C10 H8 0.9800 . ?
C10 H9 0.9800 . ?
C10 H10 0.9800 . ?
C11 H11 0.9800 . ?
C11 H12 0.9800 . ?
C11 H13 0.9800 . ?
C12 H14 0.9800 . ?
C12 H15 0.9800 . ?
C12 H16 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
C2 C1 C6 119.16(15) . . ?
C2 C1 C7 120.52(15) . . ?
C6 C1 C7 120.32(14) . . ?
C1 C2 C3 119.69(17) . . ?
C1 C2 H1 120.2 . . ?
C3 C2 H1 120.2 . . ?
C4 C3 C2 120.36(18) . . ?
C4 C3 H2 119.8 . . ?
C2 C3 H2 119.8 . . ?
C3 C4 C5 120.03(18) . . ?
C3 C4 H3 120.0 . . ?
C5 C4 H3 120.0 . . ?
C6 C5 C4 120.20(19) . . ?
C6 C5 H4 119.9 . . ?
C4 C5 H4 119.9 . . ?
C5 C6 C1 120.48(17) . . ?
C5 C6 H5 119.8 . . ?
C1 C6 H5 119.8 . . ?
N1 C7 C1 117.84(14) . . ?
N1 C7 C8 123.11(14) . . ?
C1 C7 C8 118.90(13) . . ?
C7 N1 O1 112.30(13) . . ?
N1 O1 H6 109.5 . . ?
O2 C8 N2 124.66(15) . . ?
O2 C8 C7 119.25(14) . . ?
N2 C8 C7 116.09(13) . . ?
C8 N2 C9 125.59(13) . . ?
C8 N2 H7 117.2 . . ?
C9 N2 H7 117.2 . . ?
N2 C9 C10 110.80(16) . . ?
N2 C9 C11 106.97(15) . . ?
C10 C9 C11 109.26(19) . . ?
N2 C9 C12 108.06(15) . . ?
C10 C9 C12 111.1(2) . . ?
C11 C9 C12 110.6(2) . . ?
C9 C10 H8 109.5 . . ?
C9 C10 H9 109.5 . . ?
H8 C10 H9 109.5 . . ?
C9 C10 H10 109.5 . . ?
H8 C10 H10 109.5 . . ?
H9 C10 H10 109.5 . . ?
C9 C11 H11 109.5 . . ?
C9 C11 H12 109.5 . . ?
H11 C11 H12 109.5 . . ?
C9 C11 H13 109.5 . . ?
H11 C11 H13 109.5 . . ?
H12 C11 H13 109.5 . . ?
C9 C12 H14 109.5 . . ?
C9 C12 H15 109.5 . . ?
H14 C12 H15 109.5 . . ?
C9 C12 H16 109.5 . . ?
H14 C12 H16 109.5 . . ?
H15 C12 H16 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
C6 C1 C2 C3 2.3(3) . . . . ?
C7 C1 C2 C3 -177.88(15) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C4 C5 C6 C1 1.5(3) . . . . ?
C2 C1 C6 C5 -3.1(3) . . . . ?
C7 C1 C6 C5 177.07(17) . . . . ?
C2 C1 C7 N1 149.30(15) . . . . ?
C6 C1 C7 N1 -30.9(2) . . . . ?
C2 C1 C7 C8 -34.9(2) . . . . ?
C6 C1 C7 C8 144.90(16) . . . . ?
C1 C7 N1 O1 177.00(12) . . . . ?
C8 C7 N1 O1 1.4(2) . . . . ?
N1 C7 C8 O2 109.73(19) . . . . ?
C1 C7 C8 O2 -65.82(19) . . . . ?
N1 C7 C8 N2 -70.3(2) . . . . ?
C1 C7 C8 N2 114.11(16) . . . . ?
O2 C8 N2 C9 -8.9(3) . . . . ?
C7 C8 N2 C9 171.21(14) . . . . ?
C8 N2 C9 C10 59.9(2) . . . . ?
C8 N2 C9 C11 178.94(19) . . . . ?
C8 N2 C9 C12 -61.9(2) . . . . ?

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.035

_shelxl_version_number           2014-3

