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

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#                                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
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 N O2'
_chemical_formula_weight         315.36

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                   13.716(5)
_cell_length_b                   8.084(5)
_cell_length_c                   15.868(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 100.602(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1729.4(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9770
_exptl_absorpt_correction_T_max  0.9846
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11788
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3043
_reflns_number_gt                2366
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.1000P)²+0.0649P] 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         3043
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1497
_refine_ls_wR_factor_gt          0.1329
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
N1 N 0.33958(10) 1.08165(16) 0.52929(7) 0.0592(4) Uani 1 1 d . . .
C4 C 0.35031(11) 1.17691(18) 0.45689(9) 0.0529(4) Uani 1 1 d . . .
O1 O 0.06434(9) 0.14084(15) 0.46656(8) 0.0731(4) Uani 1 1 d . . .
C13 C 0.29328(11) 0.92547(19) 0.52217(9) 0.0525(4) Uani 1 1 d . . .
C19 C 0.15049(11) 0.4539(2) 0.50144(11) 0.0590(4) Uani 1 1 d . . .
H19 H 0.1527 0.3992 0.4502 0.071 Uiso 1 1 calc R . .
C7 C 0.38960(11) 1.13371(19) 0.61233(9) 0.0540(4) Uani 1 1 d . . .
C8 C 0.37112(12) 1.2867(2) 0.64390(10) 0.0635(5) Uani 1 1 d . . .
H8 H 0.3249 1.3571 0.6119 0.076 Uiso 1 1 calc R . .
C14 C 0.24332(13) 0.8703(2) 0.58594(10) 0.0625(4) Uani 1 1 d . . .
H14 H 0.2409 0.9378 0.6329 0.075 Uiso 1 1 calc R . .
C18 C 0.29609(11) 0.82106(19) 0.45334(10) 0.0578(4) Uani 1 1 d . . .
H18 H 0.3301 0.8532 0.4105 0.069 Uiso 1 1 calc R . .
O2 O 0.01590(11) 0.14624(17) 0.59199(8) 0.0863(4) Uani 1 1 d . . .
H2 H -0.0095 0.0580 0.5745 0.130 Uiso 1 1 calc R . .
C21 C 0.05969(11) 0.2119(2) 0.53329(11) 0.0601(4) Uani 1 1 d . . .
C17 C 0.24895(12) 0.67037(19) 0.44797(10) 0.0592(4) Uani 1 1 d . . .
H17 H 0.2507 0.6034 0.4006 0.071 Uiso 1 1 calc R . .
C20 C 0.10367(12) 0.3739(2) 0.55551(11) 0.0663(5) Uani 1 1 d . . .
H20 H 0.0990 0.4218 0.6079 0.080 Uiso 1 1 calc R . .
C3 C 0.27841(13) 1.1727(2) 0.38282(10) 0.0621(4) Uani 1 1 d . . .
H3 H 0.2220 1.1078 0.3808 0.074 Uiso 1 1 calc R . .
C16 C 0.19880(11) 0.61485(18) 0.51105(10) 0.0555(4) Uani 1 1 d . . .
C15 C 0.19802(12) 0.7195(2) 0.58091(11) 0.0640(4) Uani 1 1 d . . .
H15 H 0.1660 0.6858 0.6248 0.077 Uiso 1 1 calc R . .
C5 C 0.43186(12) 1.2785(2) 0.45867(11) 0.0638(4) Uani 1 1 d . . .
H5 H 0.4803 1.2840 0.5080 0.077 Uiso 1 1 calc R . .
C9 C 0.42186(14) 1.3353(2) 0.72389(12) 0.0772(5) Uani 1 1 d . . .
H9 H 0.4098 1.4387 0.7455 0.093 Uiso 1 1 calc R . .
C6 C 0.44194(16) 1.3716(2) 0.38822(13) 0.0777(5) Uani 1 1 d . . .
H6 H 0.4967 1.4404 0.3906 0.093 Uiso 1 1 calc R . .
C12 C 0.45739(13) 1.0305(2) 0.66103(11) 0.0745(5) Uani 1 1 d . . .
H12 H 0.4700 0.9267 0.6402 0.089 Uiso 1 1 calc R . .
C2 C 0.29052(15) 1.2646(2) 0.31232(11) 0.0752(5) Uani 1 1 d . . .
H2A H 0.2427 1.2593 0.2626 0.090 Uiso 1 1 calc R . .
C1 C 0.37201(17) 1.3638(2) 0.31440(13) 0.0843(6) Uani 1 1 d . . .
H1 H 0.3798 1.4250 0.2664 0.101 Uiso 1 1 calc R . .
C10 C 0.48940(15) 1.2316(3) 0.77095(12) 0.0877(6) Uani 1 1 d . . .
H10 H 0.5238 1.2652 0.8243 0.105 Uiso 1 1 calc R . .
C11 C 0.50654(14) 1.0802(3) 0.74030(12) 0.0919(7) Uani 1 1 d . . .
H11 H 0.5518 1.0095 0.7731 0.110 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
N1 C13 1.408(2) . ?
N1 C4 1.4131(19) . ?
N1 C7 1.4322(18) . ?
C4 C5 1.384(2) . ?
C4 C3 1.389(2) . ?
O1 C21 1.217(2) . ?
C13 C18 1.386(2) . ?
C13 C14 1.396(2) . ?
C19 C20 1.330(2) . ?
C19 C16 1.455(2) . ?
C19 H19 0.9300 . ?
C7 C8 1.376(2) . ?
C7 C12 1.376(2) . ?
C8 C9 1.387(2) . ?
C8 H8 0.9300 . ?
C14 C15 1.364(2) . ?
C14 H14 0.9300 . ?
C18 C17 1.374(2) . ?
C18 H18 0.9300 . ?
O2 C21 1.310(2) . ?
O2 H2 0.8200 . ?
C21 C20 1.458(3) . ?
C17 C16 1.389(2) . ?
C17 H17 0.9300 . ?
C20 H20 0.9300 . ?
C3 C2 1.378(2) . ?
C3 H3 0.9300 . ?
C16 C15 1.396(2) . ?
C15 H15 0.9300 . ?
C5 C6 1.375(2) . ?
C5 H5 0.9300 . ?
C9 C10 1.365(3) . ?
C9 H9 0.9300 . ?
C6 C1 1.372(3) . ?
C6 H6 0.9300 . ?
C12 C11 1.373(3) . ?
C12 H12 0.9300 . ?
C2 C1 1.371(3) . ?
C2 H2A 0.9300 . ?
C1 H1 0.9300 . ?
C10 C11 1.353(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?

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
C13 N1 C4 122.42(11) . . ?
C13 N1 C7 118.02(12) . . ?
C4 N1 C7 118.94(12) . . ?
C5 C4 C3 118.51(15) . . ?
C5 C4 N1 120.77(14) . . ?
C3 C4 N1 120.71(14) . . ?
C18 C13 C14 117.71(15) . . ?
C18 C13 N1 122.10(13) . . ?
C14 C13 N1 120.18(13) . . ?
C20 C19 C16 129.15(16) . . ?
C20 C19 H19 115.4 . . ?
C16 C19 H19 115.4 . . ?
C8 C7 C12 119.43(15) . . ?
C8 C7 N1 120.67(14) . . ?
C12 C7 N1 119.89(14) . . ?
C7 C8 C9 119.51(17) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C15 C14 C13 121.50(15) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C17 C18 C13 120.50(14) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
C21 O2 H2 109.5 . . ?
O1 C21 O2 122.12(16) . . ?
O1 C21 C20 123.31(15) . . ?
O2 C21 C20 114.56(16) . . ?
C18 C17 C16 122.09(14) . . ?
C18 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C19 C20 C21 120.53(16) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C2 C3 C4 120.05(17) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C17 C16 C15 116.97(15) . . ?
C17 C16 C19 119.31(14) . . ?
C15 C16 C19 123.72(14) . . ?
C14 C15 C16 121.21(15) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C6 C5 C4 120.65(17) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C10 C9 C8 120.17(18) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C1 C6 C5 120.66(17) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C11 C12 C7 120.27(19) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 119.9 . . ?
C1 C2 C3 121.01(18) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 H2A 119.5 . . ?
C2 C1 C6 119.08(17) . . ?
C2 C1 H1 120.5 . . ?
C6 C1 H1 120.5 . . ?
C11 C10 C9 120.25(18) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?

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
C13 N1 C4 C5 -147.29(15) . . . . ?
C7 N1 C4 C5 23.5(2) . . . . ?
C13 N1 C4 C3 33.8(2) . . . . ?
C7 N1 C4 C3 -155.39(14) . . . . ?
C4 N1 C13 C18 30.5(2) . . . . ?
C7 N1 C13 C18 -140.36(15) . . . . ?
C4 N1 C13 C14 -150.12(15) . . . . ?
C7 N1 C13 C14 39.0(2) . . . . ?
C13 N1 C7 C8 -129.71(16) . . . . ?
C4 N1 C7 C8 59.1(2) . . . . ?
C13 N1 C7 C12 50.7(2) . . . . ?
C4 N1 C7 C12 -120.50(17) . . . . ?
C12 C7 C8 C9 0.7(2) . . . . ?
N1 C7 C8 C9 -178.87(15) . . . . ?
C18 C13 C14 C15 -0.5(2) . . . . ?
N1 C13 C14 C15 -179.83(14) . . . . ?
C14 C13 C18 C17 1.5(2) . . . . ?
N1 C13 C18 C17 -179.15(14) . . . . ?
C13 C18 C17 C16 -1.3(2) . . . . ?
C16 C19 C20 C21 179.89(14) . . . . ?
O1 C21 C20 C19 1.2(3) . . . . ?
O2 C21 C20 C19 179.90(15) . . . . ?
C5 C4 C3 C2 1.9(2) . . . . ?
N1 C4 C3 C2 -179.16(15) . . . . ?
C18 C17 C16 C15 0.1(2) . . . . ?
C18 C17 C16 C19 -179.95(14) . . . . ?
C20 C19 C16 C17 176.01(16) . . . . ?
C20 C19 C16 C15 -4.1(3) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C17 C16 C15 C14 1.0(2) . . . . ?
C19 C16 C15 C14 -178.99(15) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
N1 C4 C5 C6 -179.76(15) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
C8 C7 C12 C11 -0.3(3) . . . . ?
N1 C7 C12 C11 179.24(17) . . . . ?
C4 C3 C2 C1 -1.3(3) . . . . ?
C3 C2 C1 C6 -0.3(3) . . . . ?
C5 C6 C1 C2 1.4(3) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C9 C10 C11 C12 1.1(3) . . . . ?
C7 C12 C11 C10 -0.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.031
_database_code_depnum_ccdc_archive 'CCDC 976845'
