# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_r131022b1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 N2 O3'
_chemical_formula_weight         260.29

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.7179(9)
_cell_length_b                   31.177(6)
_cell_length_c                   9.2903(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.99(3)
_cell_angle_gamma                90.00
_cell_volume                     1365.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2055
_cell_measurement_theta_min      2.2886
_cell_measurement_theta_max      27.7751

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.2000
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5918
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   CrystalClear

_exptl_special_details           
; 
???? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10094
_diffrn_reflns_av_R_equivalents  0.1475
_diffrn_reflns_av_sigmaI/netI    0.1799
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.31
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2606
_reflns_number_gt                848
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0986P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.034(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2606
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1805
_refine_ls_R_factor_gt           0.0909
_refine_ls_wR_factor_ref         0.2720
_refine_ls_wR_factor_gt          0.2120
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_restrained_S_all      0.939
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1305(7) 0.40106(12) -0.1627(4) 0.0716(12) Uani 1 1 d . . .
O2 O 0.3939(9) 0.27887(12) 0.3169(4) 0.0900(14) Uani 1 1 d . . .
O3 O 0.1302(8) 0.32176(10) 0.4550(4) 0.0731(12) Uani 1 1 d . . .
N1 N 0.4710(8) 0.39548(13) 0.0750(4) 0.0551(11) Uani 1 1 d . . .
N2 N 0.5695(9) 0.40826(13) -0.0583(5) 0.0553(11) Uani 1 1 d . . .
H2 H 0.774(10) 0.4026(14) -0.075(5) 0.083 Uiso 1 1 d . . .
C1 C 0.6522(11) 0.32004(15) 0.0542(6) 0.0731(17) Uani 1 1 d . . .
H1A H 0.5560 0.3125 -0.0350 0.110 Uiso 1 1 calc R . .
H1B H 0.6705 0.2951 0.1143 0.110 Uiso 1 1 calc R . .
H1C H 0.8372 0.3310 0.0351 0.110 Uiso 1 1 calc R . .
C2 C 0.4850(10) 0.35366(15) 0.1296(5) 0.0559(13) Uani 1 1 d . . .
C3 C 0.3255(9) 0.35228(15) 0.2503(5) 0.0534(13) Uani 1 1 d . . .
C4 C 0.1973(9) 0.39479(15) 0.2699(5) 0.0507(12) Uani 1 1 d . . .
C5 C 0.0071(10) 0.41258(15) 0.3666(5) 0.0563(13) Uani 1 1 d . . .
H5 H -0.0633 0.3962 0.4410 0.068 Uiso 1 1 calc R . .
C6 C -0.0738(10) 0.45543(17) 0.3485(6) 0.0665(15) Uani 1 1 d . . .
H6 H -0.1949 0.4677 0.4137 0.080 Uiso 1 1 calc R . .
C7 C 0.0229(11) 0.48026(17) 0.2347(6) 0.0687(15) Uani 1 1 d . . .
H7 H -0.0400 0.5084 0.2242 0.082 Uiso 1 1 calc R . .
C8 C 0.2107(10) 0.46376(16) 0.1373(6) 0.0615(14) Uani 1 1 d . . .
H8 H 0.2806 0.4804 0.0635 0.074 Uiso 1 1 calc R . .
C9 C 0.2903(9) 0.42044(15) 0.1559(5) 0.0504(12) Uani 1 1 d . . .
C10 C 0.3838(11) 0.40844(15) -0.1751(6) 0.0585(14) Uani 1 1 d . . .
C11 C 0.5138(11) 0.41890(17) -0.3180(6) 0.0758(17) Uani 1 1 d . . .
H11A H 0.4433 0.3992 -0.3902 0.114 Uiso 1 1 calc R . .
H11B H 0.7164 0.4164 -0.3084 0.114 Uiso 1 1 calc R . .
H11C H 0.4640 0.4477 -0.3458 0.114 Uiso 1 1 calc R . .
C12 C 0.2920(11) 0.31392(17) 0.3396(6) 0.0651(15) Uani 1 1 d . . .
C13 C 0.0641(13) 0.28502(17) 0.5434(6) 0.086(2) Uani 1 1 d . . .
H13A H 0.2373 0.2713 0.5790 0.103 Uiso 1 1 calc R . .
H13B H -0.0463 0.2643 0.4876 0.103 Uiso 1 1 calc R . .
C14 C -0.1018(14) 0.30108(19) 0.6660(7) 0.103(2) Uani 1 1 d . . .
H14A H 0.0096 0.3216 0.7204 0.154 Uiso 1 1 calc R . .
H14B H -0.1490 0.2775 0.7271 0.154 Uiso 1 1 calc R . .
H14C H -0.2727 0.3145 0.6295 0.154 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.036(2) 0.113(3) 0.066(3) -0.004(2) 0.0097(19) -0.0049(18)
O2 0.119(4) 0.067(3) 0.086(3) 0.000(2) 0.035(3) 0.014(2)
O3 0.091(3) 0.064(2) 0.065(3) 0.0113(18) 0.025(2) -0.0017(18)
N1 0.045(3) 0.079(3) 0.042(3) 0.006(2) 0.011(2) -0.002(2)
N2 0.034(2) 0.090(3) 0.043(3) 0.008(2) 0.008(2) -0.003(2)
C1 0.067(4) 0.081(4) 0.073(4) -0.008(3) 0.025(3) 0.009(3)
C2 0.050(3) 0.071(3) 0.046(3) 0.002(2) 0.005(2) -0.004(2)
C3 0.048(3) 0.070(3) 0.043(3) -0.001(2) 0.008(2) 0.000(2)
C4 0.043(3) 0.070(3) 0.039(3) -0.002(2) 0.006(2) 0.000(2)
C5 0.059(3) 0.067(3) 0.043(3) 0.002(2) 0.010(2) -0.002(2)
C6 0.062(4) 0.080(4) 0.058(4) -0.009(3) 0.014(3) 0.016(3)
C7 0.072(4) 0.064(3) 0.070(4) -0.003(3) 0.007(3) 0.008(3)
C8 0.059(4) 0.069(3) 0.057(4) 0.008(3) 0.011(3) 0.000(3)
C9 0.036(3) 0.071(3) 0.044(3) 0.001(2) 0.003(2) -0.001(2)
C10 0.047(3) 0.073(3) 0.056(4) -0.002(3) 0.012(3) 0.004(3)
C11 0.063(4) 0.112(5) 0.053(4) 0.005(3) 0.012(3) 0.002(3)
C12 0.076(4) 0.068(4) 0.053(4) -0.001(3) 0.018(3) 0.000(3)
C13 0.113(5) 0.071(4) 0.076(5) 0.021(3) 0.036(4) -0.004(3)
C14 0.140(6) 0.089(4) 0.082(5) 0.014(4) 0.046(4) -0.017(4)

_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 C10 1.226(5) . ?
O2 C12 1.215(5) . ?
O3 C12 1.360(6) . ?
O3 C13 1.450(6) . ?
N1 C9 1.393(5) . ?
N1 N2 1.395(5) . ?
N1 C2 1.400(6) . ?
N2 C10 1.371(6) . ?
N2 H2 1.00(5) . ?
C1 C2 1.500(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.373(6) . ?
C3 C12 1.467(6) . ?
C3 C4 1.471(6) . ?
C4 C5 1.405(6) . ?
C4 C9 1.409(6) . ?
C5 C6 1.398(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.399(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.387(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.411(6) . ?
C8 H8 0.9300 . ?
C10 C11 1.517(6) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.491(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C12 O3 C13 116.3(4) . . ?
C9 N1 N2 123.2(4) . . ?
C9 N1 C2 110.3(4) . . ?
N2 N1 C2 125.1(4) . . ?
C10 N2 N1 118.7(4) . . ?
C10 N2 H2 118(3) . . ?
N1 N2 H2 116(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 N1 107.7(4) . . ?
C3 C2 C1 132.2(5) . . ?
N1 C2 C1 120.1(4) . . ?
C2 C3 C12 124.1(5) . . ?
C2 C3 C4 108.2(4) . . ?
C12 C3 C4 127.7(5) . . ?
C5 C4 C9 118.6(4) . . ?
C5 C4 C3 135.2(4) . . ?
C9 C4 C3 106.2(4) . . ?
C6 C5 C4 118.6(4) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C7 121.6(5) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 121.3(5) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 116.7(5) . . ?
C7 C8 H8 121.7 . . ?
C9 C8 H8 121.7 . . ?
N1 C9 C4 107.5(4) . . ?
N1 C9 C8 129.3(4) . . ?
C4 C9 C8 123.1(4) . . ?
O1 C10 N2 121.5(5) . . ?
O1 C10 C11 123.2(5) . . ?
N2 C10 C11 115.3(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 O3 122.4(5) . . ?
O2 C12 C3 125.7(5) . . ?
O3 C12 C3 111.9(4) . . ?
O3 C13 C14 107.3(4) . . ?
O3 C13 H13A 110.3 . . ?
C14 C13 H13A 110.3 . . ?
O3 C13 H13B 110.3 . . ?
C14 C13 H13B 110.3 . . ?
H13A C13 H13B 108.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C9 N1 N2 C10 -72.2(6) . . . . ?
C2 N1 N2 C10 92.8(6) . . . . ?
C9 N1 C2 C3 -3.2(5) . . . . ?
N2 N1 C2 C3 -169.9(4) . . . . ?
C9 N1 C2 C1 176.1(4) . . . . ?
N2 N1 C2 C1 9.4(7) . . . . ?
N1 C2 C3 C12 -178.9(4) . . . . ?
C1 C2 C3 C12 2.0(9) . . . . ?
N1 C2 C3 C4 2.0(5) . . . . ?
C1 C2 C3 C4 -177.2(5) . . . . ?
C2 C3 C4 C5 176.4(5) . . . . ?
C12 C3 C4 C5 -2.8(9) . . . . ?
C2 C3 C4 C9 -0.1(5) . . . . ?
C12 C3 C4 C9 -179.2(5) . . . . ?
C9 C4 C5 C6 -2.2(7) . . . . ?
C3 C4 C5 C6 -178.3(5) . . . . ?
C4 C5 C6 C7 2.0(8) . . . . ?
C5 C6 C7 C8 -2.0(8) . . . . ?
C6 C7 C8 C9 2.2(8) . . . . ?
N2 N1 C9 C4 170.1(4) . . . . ?
C2 N1 C9 C4 3.1(5) . . . . ?
N2 N1 C9 C8 -11.6(8) . . . . ?
C2 N1 C9 C8 -178.6(5) . . . . ?
C5 C4 C9 N1 -179.0(4) . . . . ?
C3 C4 C9 N1 -1.8(5) . . . . ?
C5 C4 C9 C8 2.6(7) . . . . ?
C3 C4 C9 C8 179.8(4) . . . . ?
C7 C8 C9 N1 179.4(5) . . . . ?
C7 C8 C9 C4 -2.6(7) . . . . ?
N1 N2 C10 O1 6.0(7) . . . . ?
N1 N2 C10 C11 -174.8(4) . . . . ?
C13 O3 C12 O2 -5.3(8) . . . . ?
C13 O3 C12 C3 174.9(4) . . . . ?
C2 C3 C12 O2 -1.7(9) . . . . ?
C4 C3 C12 O2 177.3(5) . . . . ?
C2 C3 C12 O3 178.1(4) . . . . ?
C4 C3 C12 O3 -2.9(7) . . . . ?
C12 O3 C13 C14 177.5(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 983540'
