# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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
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# 
#  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_1

_audit_creation_date             2013-09-10T19:42:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17 H16 N2 O3'
_chemical_formula_sum            'C17 H16 N2 O3'
_chemical_formula_weight         296.32
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121
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                   9.3671(6)
_cell_length_b                   9.5385(7)
_cell_length_c                   17.0984(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1527.71(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    4631
_cell_measurement_theta_min      4.64
_cell_measurement_theta_max      42.95

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prisms
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_number            1016
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.31
_diffrn_reflns_theta_max         43.32
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.93
_reflns_number_total             1016
_reflns_number_gt                843
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_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'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0871P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0048(8)
_refine_ls_number_reflns         1016
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1197
_refine_ls_wR_factor_gt          0.116
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881, 375 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.0(7)
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.042

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.3720(7) 0.9224(6) 0.7284(3) 0.0417(16) Uani 1 1 d . . .
H1 H 0.3272 1.0093 0.7102 0.05 Uiso 1 1 calc R . .
C2 C 0.3669(6) 0.9212(9) 0.8165(4) 0.0410(16) Uani 1 1 d . . .
C3 C 0.3509(6) 1.0452(8) 0.8574(5) 0.0518(17) Uani 1 1 d . . .
H3 H 0.3401 1.1286 0.8299 0.062 Uiso 1 1 calc R . .
C4 C 0.3504(6) 1.0478(8) 0.9380(5) 0.0535(18) Uani 1 1 d . . .
H4 H 0.3394 1.1327 0.9641 0.064 Uiso 1 1 calc R . .
C5 C 0.3662(6) 0.9263(11) 0.9802(4) 0.0466(17) Uani 1 1 d . . .
C6 C 0.3821(7) 0.8022(9) 0.9403(5) 0.064(2) Uani 1 1 d . . .
H6 H 0.393 0.7187 0.9678 0.077 Uiso 1 1 calc R . .
C7 C 0.3819(7) 0.8008(8) 0.8597(5) 0.0629(19) Uani 1 1 d . . .
H7 H 0.3922 0.7157 0.8338 0.075 Uiso 1 1 calc R . .
O8 O 0.3623(4) 0.9404(4) 1.0600(3) 0.0624(13) Uani 1 1 d . . .
C9 C 0.3924(8) 0.8173(8) 1.1046(4) 0.096(3) Uani 1 1 d . . .
H91 H 0.3189 0.7489 1.0957 0.144 Uiso 1 1 calc R . .
H92 H 0.3955 0.8407 1.1592 0.144 Uiso 1 1 calc R . .
H93 H 0.4829 0.7794 1.0888 0.144 Uiso 1 1 calc R . .
C10 C 0.2918(7) 0.7996(8) 0.6921(3) 0.0508(19) Uani 1 1 d . . .
H101 H 0.2994 0.8054 0.6356 0.061 Uiso 1 1 calc R . .
H102 H 0.3365 0.7128 0.7086 0.061 Uiso 1 1 calc R . .
N11 N 0.1362(7) 0.7960(10) 0.7144(3) 0.0593(16) Uani 1 1 d . . .
O12 O 0.0769(5) 0.9041(7) 0.7308(3) 0.0851(19) Uani 1 1 d . . .
O13 O 0.0805(5) 0.6816(7) 0.7150(3) 0.098(2) Uani 1 1 d . . .
C14 C 0.5233(8) 0.9179(7) 0.6968(5) 0.0438(17) Uani 1 1 d . . .
C15 C 0.6418(11) 0.9102(6) 0.7407(4) 0.0541(19) Uani 1 1 d . . .
H15 H 0.6428 0.9063 0.7951 0.065 Uiso 1 1 calc R . .
N16 N 0.7615(6) 0.9091(5) 0.6940(5) 0.0621(16) Uani 1 1 d . . .
H16 H 0.8486 0.9041 0.7096 0.075 Uiso 1 1 calc R . .
C17 C 0.7158(11) 0.9173(7) 0.6185(5) 0.0516(18) Uani 1 1 d . . .
C18 C 0.5675(10) 0.9246(6) 0.6171(4) 0.0448(17) Uani 1 1 d . . .
C19 C 0.4993(7) 0.9343(7) 0.5452(5) 0.0564(19) Uani 1 1 d . . .
H19 H 0.4001 0.9374 0.5429 0.068 Uiso 1 1 calc R . .
C20 C 0.5784(11) 0.9393(7) 0.4772(4) 0.071(2) Uani 1 1 d . . .
H20 H 0.5328 0.9477 0.4291 0.085 Uiso 1 1 calc R . .
C21 C 0.7271(14) 0.9316(8) 0.4808(5) 0.079(2) Uani 1 1 d . . .
H21 H 0.7795 0.9328 0.4346 0.095 Uiso 1 1 calc R . .
C22 C 0.7980(8) 0.9225(8) 0.5510(7) 0.075(2) Uani 1 1 d . . .
H22 H 0.8972 0.9198 0.5532 0.09 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.508(7) . ?
C1 C14 1.518(8) . ?
C1 C10 1.523(7) . ?
C1 H1 0.98 . ?
C2 C7 1.373(7) . ?
C2 C3 1.381(7) . ?
C3 C4 1.379(7) . ?
C3 H3 0.93 . ?
C4 C5 1.373(8) . ?
C4 H4 0.93 . ?
C5 O8 1.372(6) . ?
C5 C6 1.374(8) . ?
C6 C7 1.377(7) . ?
C6 H6 0.93 . ?
C7 H7 0.93 . ?
O8 C9 1.428(7) . ?
C9 H91 0.96 . ?
C9 H92 0.96 . ?
C9 H93 0.96 . ?
C10 N11 1.507(7) . ?
C10 H101 0.97 . ?
C10 H102 0.97 . ?
N11 O12 1.204(7) . ?
N11 O13 1.209(7) . ?
C14 C15 1.342(7) . ?
C14 C18 1.424(8) . ?
C15 N16 1.377(7) . ?
C15 H15 0.93 . ?
N16 C17 1.362(8) . ?
N16 H16 0.86 . ?
C17 C22 1.389(9) . ?
C17 C18 1.391(7) . ?
C18 C19 1.389(8) . ?
C19 C20 1.381(8) . ?
C19 H19 0.93 . ?
C20 C21 1.396(10) . ?
C20 H20 0.93 . ?
C21 C22 1.374(9) . ?
C21 H21 0.93 . ?
C22 H22 0.93 . ?

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 C14 112.6(5) . . ?
C2 C1 C10 112.7(5) . . ?
C14 C1 C10 107.1(5) . . ?
C2 C1 H1 108.1 . . ?
C14 C1 H1 108.1 . . ?
C10 C1 H1 108.1 . . ?
C7 C2 C3 117.0(5) . . ?
C7 C2 C1 122.7(7) . . ?
C3 C2 C1 120.2(7) . . ?
C4 C3 C2 121.5(6) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 120.6(6) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
O8 C5 C4 115.9(8) . . ?
O8 C5 C6 125.5(8) . . ?
C4 C5 C6 118.6(6) . . ?
C5 C6 C7 120.3(6) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C6 122.1(6) . . ?
C2 C7 H7 119 . . ?
C6 C7 H7 119 . . ?
C5 O8 C9 116.4(5) . . ?
O8 C9 H91 109.5 . . ?
O8 C9 H92 109.5 . . ?
H91 C9 H92 109.5 . . ?
O8 C9 H93 109.5 . . ?
H91 C9 H93 109.5 . . ?
H92 C9 H93 109.5 . . ?
N11 C10 C1 113.1(6) . . ?
N11 C10 H101 109 . . ?
C1 C10 H101 109 . . ?
N11 C10 H102 109 . . ?
C1 C10 H102 109 . . ?
H101 C10 H102 107.8 . . ?
O12 N11 O13 124.9(7) . . ?
O12 N11 C10 119.0(7) . . ?
O13 N11 C10 116.1(8) . . ?
C15 C14 C18 107.3(6) . . ?
C15 C14 C1 125.0(7) . . ?
C18 C14 C1 127.6(8) . . ?
C14 C15 N16 110.4(5) . . ?
C14 C15 H15 124.8 . . ?
N16 C15 H15 124.8 . . ?
C17 N16 C15 107.0(5) . . ?
C17 N16 H16 126.5 . . ?
C15 N16 H16 126.5 . . ?
N16 C17 C22 128.0(10) . . ?
N16 C17 C18 109.4(7) . . ?
C22 C17 C18 122.5(9) . . ?
C19 C18 C17 118.5(8) . . ?
C19 C18 C14 135.7(9) . . ?
C17 C18 C14 105.8(6) . . ?
C20 C19 C18 120.1(6) . . ?
C20 C19 H19 120 . . ?
C18 C19 H19 120 . . ?
C19 C20 C21 119.7(7) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C22 C21 C20 121.7(7) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C17 117.4(7) . . ?
C21 C22 H22 121.3 . . ?
C17 C22 H22 121.3 . . ?

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
C14 C1 C2 C7 -79.9(7) . . . . ?
C10 C1 C2 C7 41.4(8) . . . . ?
C14 C1 C2 C3 98.1(7) . . . . ?
C10 C1 C2 C3 -140.6(6) . . . . ?
C7 C2 C3 C4 0.2(9) . . . . ?
C1 C2 C3 C4 -177.9(6) . . . . ?
C2 C3 C4 C5 0.0(10) . . . . ?
C3 C4 C5 O8 -179.2(6) . . . . ?
C3 C4 C5 C6 -0.1(9) . . . . ?
O8 C5 C6 C7 178.9(5) . . . . ?
C4 C5 C6 C7 -0.1(9) . . . . ?
C3 C2 C7 C6 -0.4(9) . . . . ?
C1 C2 C7 C6 177.7(6) . . . . ?
C5 C6 C7 C2 0.4(11) . . . . ?
C4 C5 O8 C9 -174.1(6) . . . . ?
C6 C5 O8 C9 6.9(9) . . . . ?
C2 C1 C10 N11 59.2(7) . . . . ?
C14 C1 C10 N11 -176.4(5) . . . . ?
C1 C10 N11 O12 27.2(8) . . . . ?
C1 C10 N11 O13 -152.2(5) . . . . ?
C2 C1 C14 C15 1.5(9) . . . . ?
C10 C1 C14 C15 -122.9(6) . . . . ?
C2 C1 C14 C18 -176.6(6) . . . . ?
C10 C1 C14 C18 59.0(8) . . . . ?
C18 C14 C15 N16 -1.1(6) . . . . ?
C1 C14 C15 N16 -179.5(6) . . . . ?
C14 C15 N16 C17 0.5(6) . . . . ?
C15 N16 C17 C22 178.5(7) . . . . ?
C15 N16 C17 C18 0.4(7) . . . . ?
N16 C17 C18 C19 179.7(5) . . . . ?
C22 C17 C18 C19 1.5(11) . . . . ?
N16 C17 C18 C14 -1.0(8) . . . . ?
C22 C17 C18 C14 -179.3(6) . . . . ?
C15 C14 C18 C19 -179.7(7) . . . . ?
C1 C14 C18 C19 -1.3(11) . . . . ?
C15 C14 C18 C17 1.3(7) . . . . ?
C1 C14 C18 C17 179.7(6) . . . . ?
C17 C18 C19 C20 -1.3(9) . . . . ?
C14 C18 C19 C20 179.7(7) . . . . ?
C18 C19 C20 C21 1.3(10) . . . . ?
C19 C20 C21 C22 -1.6(12) . . . . ?
C20 C21 C22 C17 1.7(11) . . . . ?
N16 C17 C22 C21 -179.5(7) . . . . ?
C18 C17 C22 C21 -1.7(11) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 976490'
