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

#######################################################################
#
#                 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.
#
#  This CIF is provided on the understanding that it is used for bona
#  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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mo_dm13088_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 N2 O3'
_chemical_formula_weight         268.27

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   5.1332(14)
_cell_length_b                   35.283(10)
_cell_length_c                   7.131(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.075(5)
_cell_angle_gamma                90.00
_cell_volume                     1267.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    2467
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      27.92

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9754
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7970
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.10
_reflns_number_total             2239
_reflns_number_gt                1766
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1189P)²+3.2574P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2239
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0847
_refine_ls_wR_factor_ref         0.2559
_refine_ls_wR_factor_gt          0.2451
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_restrained_S_all      1.155
_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
N1 N 0.5655(7) 0.86951(10) 0.9355(5) 0.0208(8) Uani 1 1 d . . .
N2 N 0.6059(8) 0.83417(10) 0.9341(5) 0.0242(9) Uani 1 1 d . . .
O1 O 1.2804(6) 1.00915(9) 0.7783(4) 0.0282(8) Uani 1 1 d . . .
H1 H 1.4216 1.0155 0.8520 0.042 Uiso 1 1 calc R . .
O2 O 1.2673(6) 0.96738(8) 1.0128(4) 0.0252(8) Uani 1 1 d . . .
O3 O 0.6069(7) 0.89149(9) 1.0784(4) 0.0326(9) Uani 1 1 d . . .
C1 C 1.1720(8) 0.98096(12) 0.8524(6) 0.0188(9) Uani 1 1 d . . .
C2 C 0.9260(8) 0.96586(12) 0.7358(6) 0.0224(9) Uani 1 1 d . . .
H2 H 0.8498 0.9782 0.6199 0.027 Uiso 1 1 calc R . .
C3 C 0.8096(8) 0.93556(12) 0.7888(6) 0.0194(9) Uani 1 1 d . . .
H3 H 0.8902 0.9240 0.9060 0.023 Uiso 1 1 calc R . .
C4 C 0.5658(8) 0.91797(12) 0.6825(5) 0.0186(9) Uani 1 1 d . . .
C5 C 0.4396(9) 0.93194(12) 0.5030(6) 0.0221(9) Uani 1 1 d . . .
H5 H 0.5128 0.9533 0.4508 0.027 Uiso 1 1 calc R . .
C6 C 0.2127(9) 0.91546(13) 0.4011(6) 0.0248(10) Uani 1 1 d . . .
H6 H 0.1321 0.9256 0.2805 0.030 Uiso 1 1 calc R . .
C7 C 0.1009(9) 0.88414(13) 0.4726(6) 0.0243(10) Uani 1 1 d . . .
H7 H -0.0580 0.8733 0.4031 0.029 Uiso 1 1 calc R . .
C8 C 0.2232(9) 0.86882(12) 0.6469(6) 0.0226(10) Uani 1 1 d . . .
H8 H 0.1527 0.8468 0.6955 0.027 Uiso 1 1 calc R . .
C9 C 0.4499(8) 0.88609(11) 0.7493(6) 0.0193(9) Uani 1 1 d . . .
C10 C 0.6918(9) 0.81674(12) 1.1167(6) 0.0220(9) Uani 1 1 d . . .
C11 C 0.5655(9) 0.82179(12) 1.2709(6) 0.0249(10) Uani 1 1 d . . .
H11 H 0.4231 0.8393 1.2623 0.030 Uiso 1 1 calc R . .
C12 C 0.6482(10) 0.80114(12) 1.4377(6) 0.0270(10) Uani 1 1 d . . .
H12 H 0.5611 0.8043 1.5428 0.032 Uiso 1 1 calc R . .
C13 C 0.8587(9) 0.77591(12) 1.4503(6) 0.0266(10) Uani 1 1 d . . .
H13 H 0.9195 0.7623 1.5654 0.032 Uiso 1 1 calc R . .
C14 C 0.9795(9) 0.77065(14) 1.2945(6) 0.0282(10) Uani 1 1 d . . .
H14 H 1.1206 0.7530 1.3021 0.034 Uiso 1 1 calc R . .
C15 C 0.8963(9) 0.79087(13) 1.1289(6) 0.0266(10) Uani 1 1 d . . .
H15 H 0.9799 0.7870 1.0225 0.032 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
N1 0.0174(19) 0.0232(19) 0.0188(18) -0.0003(14) -0.0042(14) -0.0040(14)
N2 0.027(2) 0.0266(19) 0.0169(17) 0.0008(14) -0.0017(15) -0.0005(15)
O1 0.0225(17) 0.0361(18) 0.0235(16) 0.0068(13) -0.0018(13) -0.0126(14)
O2 0.0231(17) 0.0331(17) 0.0168(15) 0.0054(12) -0.0024(12) -0.0043(13)
O3 0.048(2) 0.0315(18) 0.0171(16) -0.0031(12) 0.0021(14) -0.0038(15)
C1 0.015(2) 0.024(2) 0.016(2) -0.0008(16) 0.0023(16) 0.0001(16)
C2 0.018(2) 0.029(2) 0.019(2) 0.0032(17) -0.0014(17) -0.0009(17)
C3 0.015(2) 0.029(2) 0.0136(19) 0.0007(16) 0.0024(16) 0.0013(17)
C4 0.016(2) 0.027(2) 0.0126(19) 0.0000(15) 0.0003(16) -0.0010(16)
C5 0.022(2) 0.029(2) 0.0141(19) 0.0020(16) 0.0015(17) -0.0030(18)
C6 0.023(2) 0.037(2) 0.0118(19) 0.0023(17) -0.0029(17) -0.0005(19)
C7 0.017(2) 0.033(2) 0.022(2) -0.0028(17) -0.0007(17) -0.0022(17)
C8 0.022(2) 0.025(2) 0.021(2) 0.0004(16) 0.0039(17) -0.0029(17)
C9 0.021(2) 0.021(2) 0.0149(19) -0.0004(15) 0.0002(16) 0.0015(16)
C10 0.025(2) 0.023(2) 0.0154(19) -0.0003(16) -0.0022(16) -0.0075(17)
C11 0.021(2) 0.026(2) 0.028(2) 0.0042(18) 0.0032(18) 0.0012(18)
C12 0.029(3) 0.029(2) 0.024(2) 0.0037(18) 0.0082(18) -0.0030(19)
C13 0.024(2) 0.029(2) 0.025(2) 0.0069(17) 0.0011(18) -0.0017(18)
C14 0.018(2) 0.040(3) 0.026(2) 0.0015(19) 0.0009(18) 0.0029(19)
C15 0.026(2) 0.037(2) 0.017(2) -0.0006(18) 0.0049(17) 0.000(2)

_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
N1 N2 1.264(5) . ?
N1 O3 1.266(5) . ?
N1 C9 1.468(5) . ?
N2 C10 1.431(5) . ?
O1 C1 1.301(5) . ?
O1 H1 0.8400 . ?
O2 C1 1.250(5) . ?
C1 C2 1.472(6) . ?
C2 C3 1.315(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.470(6) . ?
C3 H3 0.9500 . ?
C4 C9 1.398(6) . ?
C4 C5 1.408(6) . ?
C5 C6 1.377(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(6) . ?
C8 H8 0.9500 . ?
C10 C15 1.381(7) . ?
C10 C11 1.391(6) . ?
C11 C12 1.390(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.376(6) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

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
N2 N1 O3 127.5(3) . . ?
N2 N1 C9 115.1(3) . . ?
O3 N1 C9 117.4(3) . . ?
N1 N2 C10 116.1(3) . . ?
C1 O1 H1 109.5 . . ?
O2 C1 O1 122.8(4) . . ?
O2 C1 C2 121.4(4) . . ?
O1 C1 C2 115.8(3) . . ?
C3 C2 C1 121.3(4) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 125.7(4) . . ?
C2 C3 H3 117.1 . . ?
C4 C3 H3 117.1 . . ?
C9 C4 C5 116.1(4) . . ?
C9 C4 C3 122.7(4) . . ?
C5 C4 C3 121.2(4) . . ?
C6 C5 C4 121.8(4) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 120.7(4) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C8 119.4(4) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C7 C8 C9 119.2(4) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C4 122.8(4) . . ?
C8 C9 N1 116.9(4) . . ?
C4 C9 N1 120.2(4) . . ?
C15 C10 C11 119.9(4) . . ?
C15 C10 N2 116.0(4) . . ?
C11 C10 N2 123.7(4) . . ?
C12 C11 C10 119.8(4) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 119.8(4) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 119.8(4) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C10 120.2(4) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?

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
O3 N1 N2 C10 4.4(6) . . . . ?
C9 N1 N2 C10 -173.6(4) . . . . ?
O2 C1 C2 C3 -5.7(7) . . . . ?
O1 C1 C2 C3 174.7(4) . . . . ?
C1 C2 C3 C4 -179.4(4) . . . . ?
C2 C3 C4 C9 -178.8(4) . . . . ?
C2 C3 C4 C5 3.1(7) . . . . ?
C9 C4 C5 C6 1.0(6) . . . . ?
C3 C4 C5 C6 179.3(4) . . . . ?
C4 C5 C6 C7 -0.2(7) . . . . ?
C5 C6 C7 C8 -1.5(7) . . . . ?
C6 C7 C8 C9 2.4(7) . . . . ?
C7 C8 C9 C4 -1.6(7) . . . . ?
C7 C8 C9 N1 177.9(4) . . . . ?
C5 C4 C9 C8 -0.1(6) . . . . ?
C3 C4 C9 C8 -178.3(4) . . . . ?
C5 C4 C9 N1 -179.6(4) . . . . ?
C3 C4 C9 N1 2.2(6) . . . . ?
N2 N1 C9 C8 51.1(5) . . . . ?
O3 N1 C9 C8 -127.1(4) . . . . ?
N2 N1 C9 C4 -129.4(4) . . . . ?
O3 N1 C9 C4 52.4(5) . . . . ?
N1 N2 C10 C15 -136.1(4) . . . . ?
N1 N2 C10 C11 50.2(6) . . . . ?
C15 C10 C11 C12 0.9(7) . . . . ?
N2 C10 C11 C12 174.3(4) . . . . ?
C10 C11 C12 C13 0.8(7) . . . . ?
C11 C12 C13 C14 -2.0(7) . . . . ?
C12 C13 C14 C15 1.5(7) . . . . ?
C13 C14 C15 C10 0.2(7) . . . . ?
C11 C10 C15 C14 -1.4(7) . . . . ?
N2 C10 C15 C14 -175.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.090
_database_code_depnum_ccdc_archive 'CCDC 975924'
