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

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_x

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 N O3'
_chemical_formula_weight         291.29

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           Orthorhombic
_symmetry_space_group_name_H-M   P212121

_chemical_absolute_configuration unk

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

_cell_length_a                   8.9540(18)
_cell_length_b                   9.4550(19)
_cell_length_c                   17.176(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1454.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      10
_cell_measurement_theta_max      13

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9731
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Nonius cad4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            3006
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         25.38
_reflns_number_total             2668
_reflns_number_gt                2015
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CAD4 EXPRESS(Enraf-Nonius,1994)'
_computing_cell_refinement       'CAD4 EXPRESS'
_computing_data_reduction        'XCAD4(Harms & Wocadlo,1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0700P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.102(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(19)
_refine_ls_number_reflns         2668
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1126
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N N 0.2340(3) 0.8104(3) 0.08229(14) 0.0450(6) Uani 1 1 d . . .
O1 O -0.0175(2) 0.7609(2) 0.07536(13) 0.0554(6) Uani 1 1 d . . .
C1 C 0.1539(3) 0.6061(3) 0.14737(14) 0.0354(6) Uani 1 1 d . . .
O2 O 0.0771(2) 0.6181(2) 0.22097(10) 0.0444(5) Uani 1 1 d . . .
C2 C 0.1082(3) 0.7347(3) 0.09702(16) 0.0397(7) Uani 1 1 d . . .
O3 O -0.0886(3) 0.4913(3) 0.28885(12) 0.0674(7) Uani 1 1 d . . .
C3 C 0.3593(3) 0.7512(3) 0.11948(18) 0.0443(7) Uani 1 1 d . . .
C4 C 0.5046(4) 0.7987(4) 0.1198(2) 0.0620(10) Uani 1 1 d . . .
H4A H 0.5316 0.8814 0.0942 0.074 Uiso 1 1 calc R . .
C5 C 0.6091(4) 0.7188(5) 0.1597(2) 0.0770(12) Uani 1 1 d . . .
H5A H 0.7082 0.7482 0.1601 0.092 Uiso 1 1 calc R . .
C6 C 0.5705(4) 0.5977(5) 0.1987(2) 0.0701(11) Uani 1 1 d . . .
H6A H 0.6429 0.5472 0.2258 0.084 Uiso 1 1 calc R . .
C7 C 0.4233(3) 0.5499(4) 0.19798(18) 0.0527(8) Uani 1 1 d . . .
H7A H 0.3966 0.4673 0.2238 0.063 Uiso 1 1 calc R . .
C8 C 0.3196(3) 0.6271(3) 0.15854(15) 0.0386(7) Uani 1 1 d . . .
C9 C 0.1025(3) 0.4666(3) 0.11437(15) 0.0374(6) Uani 1 1 d . . .
C10 C 0.0112(3) 0.4080(4) 0.16594(15) 0.0515(8) Uani 1 1 d . . .
H10A H -0.0321 0.3191 0.1606 0.062 Uiso 1 1 calc R . .
C11 C -0.0118(3) 0.5015(4) 0.23185(16) 0.0485(8) Uani 1 1 d . . .
C12 C 0.1405(3) 0.4155(3) 0.03619(16) 0.0359(6) Uani 1 1 d . . .
C13 C 0.2522(3) 0.4759(3) -0.00938(15) 0.0406(7) Uani 1 1 d . . .
H13A H 0.3106 0.5482 0.0111 0.049 Uiso 1 1 calc R . .
C14 C 0.2775(3) 0.4303(3) -0.08413(17) 0.0460(7) Uani 1 1 d . . .
H14A H 0.3517 0.4729 -0.1139 0.055 Uiso 1 1 calc R . .
C15 C 0.1936(4) 0.3220(3) -0.11543(18) 0.0521(8) Uani 1 1 d . . .
H15A H 0.2106 0.2914 -0.1661 0.063 Uiso 1 1 calc R . .
C16 C 0.0855(4) 0.2607(4) -0.0710(2) 0.0639(9) Uani 1 1 d . . .
H16A H 0.0289 0.1871 -0.0915 0.077 Uiso 1 1 calc R . .
C17 C 0.0591(4) 0.3064(3) 0.00391(18) 0.0576(9) Uani 1 1 d . . .
H17A H -0.0151 0.2630 0.0333 0.069 Uiso 1 1 calc R . .
C18 C 0.2332(5) 0.9425(4) 0.0390(2) 0.0707(11) Uani 1 1 d . . .
H18A H 0.1347 0.9598 0.0191 0.106 Uiso 1 1 calc R . .
H18B H 0.3025 0.9363 -0.0035 0.106 Uiso 1 1 calc R . .
H18C H 0.2619 1.0186 0.0728 0.106 Uiso 1 1 calc R . .


_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
N C2 1.358(4) . ?
N C3 1.408(4) . ?
N C18 1.454(4) . ?
O1 C2 1.211(3) . ?
C1 O2 1.443(3) . ?
C1 C9 1.508(4) . ?
C1 C8 1.509(4) . ?
C1 C2 1.547(4) . ?
O2 C11 1.373(4) . ?
O3 C11 1.200(3) . ?
C3 C4 1.376(4) . ?
C3 C8 1.398(4) . ?
C4 C5 1.384(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.371(6) . ?
C5 H5A 0.9300 . ?
C6 C7 1.393(5) . ?
C6 H6A 0.9300 . ?
C7 C8 1.362(4) . ?
C7 H7A 0.9300 . ?
C9 C10 1.327(4) . ?
C9 C12 1.467(4) . ?
C10 C11 1.451(4) . ?
C10 H10A 0.9300 . ?
C12 C17 1.379(4) . ?
C12 C13 1.392(4) . ?
C13 C14 1.373(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.379(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.363(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.378(4) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C2 N C3 111.5(2) . . ?
C2 N C18 123.0(3) . . ?
C3 N C18 125.3(3) . . ?
O2 C1 C9 104.7(2) . . ?
O2 C1 C8 110.3(2) . . ?
C9 C1 C8 117.6(2) . . ?
O2 C1 C2 107.6(2) . . ?
C9 C1 C2 113.4(2) . . ?
C8 C1 C2 103.2(2) . . ?
C11 O2 C1 109.4(2) . . ?
O1 C2 N 127.3(3) . . ?
O1 C2 C1 125.3(2) . . ?
N C2 C1 107.4(2) . . ?
C4 C3 C8 120.8(3) . . ?
C4 C3 N 128.8(3) . . ?
C8 C3 N 110.4(2) . . ?
C3 C4 C5 117.6(3) . . ?
C3 C4 H4A 121.2 . . ?
C5 C4 H4A 121.2 . . ?
C6 C5 C4 121.8(3) . . ?
C6 C5 H5A 119.1 . . ?
C4 C5 H5A 119.1 . . ?
C5 C6 C7 120.3(3) . . ?
C5 C6 H6A 119.8 . . ?
C7 C6 H6A 119.8 . . ?
C8 C7 C6 118.4(3) . . ?
C8 C7 H7A 120.8 . . ?
C6 C7 H7A 120.8 . . ?
C7 C8 C3 121.0(3) . . ?
C7 C8 C1 131.6(3) . . ?
C3 C8 C1 107.4(2) . . ?
C10 C9 C12 128.1(3) . . ?
C10 C9 C1 107.6(2) . . ?
C12 C9 C1 124.2(2) . . ?
C9 C10 C11 110.7(3) . . ?
C9 C10 H10A 124.6 . . ?
C11 C10 H10A 124.6 . . ?
O3 C11 O2 120.5(3) . . ?
O3 C11 C10 132.0(3) . . ?
O2 C11 C10 107.5(2) . . ?
C17 C12 C13 117.4(3) . . ?
C17 C12 C9 119.4(2) . . ?
C13 C12 C9 123.1(2) . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H13A 119.5 . . ?
C12 C13 H13A 119.5 . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14A 119.7 . . ?
C15 C14 H14A 119.7 . . ?
C16 C15 C14 119.0(3) . . ?
C16 C15 H15A 120.5 . . ?
C14 C15 H15A 120.5 . . ?
C15 C16 C17 120.7(3) . . ?
C15 C16 H16A 119.6 . . ?
C17 C16 H16A 119.6 . . ?
C16 C17 C12 121.3(3) . . ?
C16 C17 H17A 119.4 . . ?
C12 C17 H17A 119.4 . . ?
N C18 H18A 109.5 . . ?
N C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 C1 O2 C11 -0.6(3) . . . . ?
C8 C1 O2 C11 -127.9(2) . . . . ?
C2 C1 O2 C11 120.3(2) . . . . ?
C3 N C2 O1 177.7(3) . . . . ?
C18 N C2 O1 2.7(4) . . . . ?
C3 N C2 C1 -2.4(3) . . . . ?
C18 N C2 C1 -177.4(3) . . . . ?
O2 C1 C2 O1 -62.1(3) . . . . ?
C9 C1 C2 O1 53.1(4) . . . . ?
C8 C1 C2 O1 -178.7(3) . . . . ?
O2 C1 C2 N 117.9(2) . . . . ?
C9 C1 C2 N -126.8(2) . . . . ?
C8 C1 C2 N 1.4(3) . . . . ?
C2 N C3 C4 -178.5(3) . . . . ?
C18 N C3 C4 -3.7(5) . . . . ?
C2 N C3 C8 2.5(3) . . . . ?
C18 N C3 C8 177.4(3) . . . . ?
C8 C3 C4 C5 0.3(5) . . . . ?
N C3 C4 C5 -178.5(3) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
C4 C5 C6 C7 1.1(6) . . . . ?
C5 C6 C7 C8 -0.7(5) . . . . ?
C6 C7 C8 C3 0.2(4) . . . . ?
C6 C7 C8 C1 -179.2(3) . . . . ?
C4 C3 C8 C7 0.0(4) . . . . ?
N C3 C8 C7 179.1(3) . . . . ?
C4 C3 C8 C1 179.5(3) . . . . ?
N C3 C8 C1 -1.5(3) . . . . ?
O2 C1 C8 C7 64.8(4) . . . . ?
C9 C1 C8 C7 -55.0(4) . . . . ?
C2 C1 C8 C7 179.5(3) . . . . ?
O2 C1 C8 C3 -114.6(2) . . . . ?
C9 C1 C8 C3 125.6(3) . . . . ?
C2 C1 C8 C3 0.1(3) . . . . ?
O2 C1 C9 C10 -1.6(3) . . . . ?
C8 C1 C9 C10 121.1(3) . . . . ?
C2 C1 C9 C10 -118.6(3) . . . . ?
O2 C1 C9 C12 173.9(2) . . . . ?
C8 C1 C9 C12 -63.4(3) . . . . ?
C2 C1 C9 C12 56.9(3) . . . . ?
C12 C9 C10 C11 -172.1(3) . . . . ?
C1 C9 C10 C11 3.2(3) . . . . ?
C1 O2 C11 O3 -178.3(3) . . . . ?
C1 O2 C11 C10 2.4(3) . . . . ?
C9 C10 C11 O3 177.2(3) . . . . ?
C9 C10 C11 O2 -3.6(3) . . . . ?
C10 C9 C12 C17 11.2(4) . . . . ?
C1 C9 C12 C17 -163.4(3) . . . . ?
C10 C9 C12 C13 -171.6(3) . . . . ?
C1 C9 C12 C13 13.8(4) . . . . ?
C17 C12 C13 C14 1.5(4) . . . . ?
C9 C12 C13 C14 -175.8(3) . . . . ?
C12 C13 C14 C15 -0.9(4) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
C14 C15 C16 C17 0.5(5) . . . . ?
C15 C16 C17 C12 0.1(5) . . . . ?
C13 C12 C17 C16 -1.1(4) . . . . ?
C9 C12 C17 C16 176.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.036
_database_code_depnum_ccdc_archive 'CCDC 987924'
