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


data_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35

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                   9.4209(6)
_cell_length_b                   18.6410(12)
_cell_length_c                   9.7949(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.6340(10)
_cell_angle_gamma                90.00
_cell_volume                     1587.65(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4434
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      28.26

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.109
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  '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            7841
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2798
_reflns_number_gt                2408
_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)+(0.0596P)²+0.4206P] 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       0.039(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2798
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1215
_refine_ls_wR_factor_gt          0.1160
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.63062(14) 0.06184(7) 0.42113(14) 0.0479(3) Uani 1 1 d . . .
C1 C 0.64826(16) 0.03668(8) 0.29550(16) 0.0470(4) Uani 1 1 d . . .
C2 C 0.73064(16) -0.02582(8) 0.33240(16) 0.0435(3) Uani 1 1 d . . .
C3 C 0.76405(16) -0.03931(8) 0.48658(16) 0.0439(4) Uani 1 1 d . . .
C4 C 0.69996(16) 0.01626(8) 0.53754(17) 0.0466(4) Uani 1 1 d . . .
C5 C 0.5788(2) 0.07421(10) 0.15061(19) 0.0638(5) Uani 1 1 d . . .
H5A H 0.6026 0.0483 0.0773 0.077 Uiso 1 1 calc R . .
H5B H 0.6199 0.1219 0.1597 0.077 Uiso 1 1 calc R . .
H5C H 0.4693 0.0766 0.1214 0.077 Uiso 1 1 calc R . .
C6 C 0.7084(2) 0.03230(10) 0.68965(19) 0.0599(4) Uani 1 1 d . . .
H6A H 0.6065 0.0395 0.6870 0.072 Uiso 1 1 calc R . .
H6B H 0.7683 0.0749 0.7259 0.072 Uiso 1 1 calc R . .
H6C H 0.7557 -0.0072 0.7539 0.072 Uiso 1 1 calc R . .
C7 C 0.86333(18) -0.09504(8) 0.58180(17) 0.0497(4) Uani 1 1 d . . .
C8 C 0.9903(2) -0.12553(10) 0.5437(2) 0.0603(4) Uani 1 1 d . . .
H8A H 1.0765 -0.1368 0.6330 0.072 Uiso 1 1 calc R . .
H8B H 1.0209 -0.0910 0.4876 0.072 Uiso 1 1 calc R . .
H8C H 0.9550 -0.1683 0.4861 0.072 Uiso 1 1 calc R . .
C9 C 0.76360(16) -0.07322(8) 0.22674(16) 0.0466(4) Uani 1 1 d . . .
C10 C 0.7123(2) -0.14326(10) 0.2060(2) 0.0619(5) Uani 1 1 d . . .
H10A H 0.6567 -0.1607 0.2594 0.074 Uiso 1 1 calc R . .
C11 C 0.7418(3) -0.18807(11) 0.1072(2) 0.0775(6) Uani 1 1 d . . .
H11A H 0.7076 -0.2353 0.0961 0.093 Uiso 1 1 calc R . .
C12 C 0.8217(2) -0.16283(12) 0.0258(2) 0.0758(6) Uani 1 1 d . . .
H12A H 0.8404 -0.1926 -0.0416 0.091 Uiso 1 1 calc R . .
C13 C 0.8734(2) -0.09369(12) 0.0446(2) 0.0698(5) Uani 1 1 d . . .
H13A H 0.9278 -0.0765 -0.0101 0.084 Uiso 1 1 calc R . .
C14 C 0.84572(19) -0.04885(10) 0.14434(18) 0.0571(4) Uani 1 1 d . . .
H14A H 0.8824 -0.0020 0.1564 0.069 Uiso 1 1 calc R . .
C15 C 0.55009(19) 0.12831(9) 0.4273(2) 0.0600(5) Uani 1 1 d . . .
H15A H 0.5117 0.1243 0.5058 0.072 Uiso 1 1 calc R . .
H15B H 0.4622 0.1340 0.3348 0.072 Uiso 1 1 calc R . .
C16 C 0.64825(19) 0.19304(9) 0.4536(2) 0.0583(4) Uani 1 1 d . . .
C17 C 0.6511(2) 0.24830(11) 0.3681(3) 0.0807(6) Uani 1 1 d . . .
H17A H 0.5855 0.2556 0.2701 0.097 Uiso 1 1 calc R . .
C18 C 0.7728(3) 0.29361(12) 0.4547(4) 0.0955(8) Uani 1 1 d . . .
H18A H 0.8016 0.3368 0.4252 0.115 Uiso 1 1 calc R . .
C19 C 0.8369(3) 0.26322(13) 0.5842(3) 0.0881(7) Uani 1 1 d . . .
H19A H 0.9206 0.2817 0.6626 0.106 Uiso 1 1 calc R . .
O1 O 0.84848(18) -0.11536(8) 0.69428(15) 0.0805(4) Uani 1 1 d . . .
O2 O 0.76319(17) 0.19985(8) 0.58862(15) 0.0772(4) Uani 1 1 d . . .


_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 C4 1.369(2) . ?
N1 C1 1.3853(19) . ?
N1 C15 1.466(2) . ?
C1 C2 1.369(2) . ?
C1 C5 1.489(2) . ?
C2 C3 1.441(2) . ?
C2 C9 1.482(2) . ?
C3 C4 1.385(2) . ?
C3 C7 1.467(2) . ?
C4 C6 1.491(2) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 O1 1.2230(19) . ?
C7 C8 1.495(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.380(2) . ?
C9 C14 1.392(2) . ?
C10 C11 1.385(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.373(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.365(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.384(2) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 C16 1.481(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.334(3) . ?
C16 O2 1.355(2) . ?
C17 C18 1.414(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.306(4) . ?
C18 H18A 0.9300 . ?
C19 O2 1.379(3) . ?
C19 H19A 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
C4 N1 C1 110.35(12) . . ?
C4 N1 C15 125.34(14) . . ?
C1 N1 C15 124.31(14) . . ?
C2 C1 N1 107.65(13) . . ?
C2 C1 C5 130.38(15) . . ?
N1 C1 C5 121.92(14) . . ?
C1 C2 C3 107.35(13) . . ?
C1 C2 C9 124.95(13) . . ?
C3 C2 C9 127.44(13) . . ?
C4 C3 C2 107.30(13) . . ?
C4 C3 C7 124.07(14) . . ?
C2 C3 C7 128.20(13) . . ?
N1 C4 C3 107.36(13) . . ?
N1 C4 C6 122.17(14) . . ?
C3 C4 C6 130.30(15) . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C3 121.74(15) . . ?
O1 C7 C8 119.13(15) . . ?
C3 C7 C8 119.08(13) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 117.72(15) . . ?
C10 C9 C2 120.74(14) . . ?
C14 C9 C2 121.54(14) . . ?
C9 C10 C11 121.32(17) . . ?
C9 C10 H10A 119.3 . . ?
C11 C10 H10A 119.3 . . ?
C12 C11 C10 120.10(19) . . ?
C12 C11 H11A 119.9 . . ?
C10 C11 H11A 119.9 . . ?
C13 C12 C11 119.46(18) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
C12 C13 C14 120.74(18) . . ?
C12 C13 H13A 119.6 . . ?
C14 C13 H13A 119.6 . . ?
C13 C14 C9 120.64(17) . . ?
C13 C14 H14A 119.7 . . ?
C9 C14 H14A 119.7 . . ?
N1 C15 C16 113.40(13) . . ?
N1 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
N1 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 O2 109.80(18) . . ?
C17 C16 C15 133.0(2) . . ?
O2 C16 C15 117.16(16) . . ?
C16 C17 C18 107.0(2) . . ?
C16 C17 H17A 126.5 . . ?
C18 C17 H17A 126.5 . . ?
C19 C18 C17 106.8(2) . . ?
C19 C18 H18A 126.6 . . ?
C17 C18 H18A 126.6 . . ?
C18 C19 O2 110.6(2) . . ?
C18 C19 H19A 124.7 . . ?
O2 C19 H19A 124.7 . . ?
C16 O2 C19 105.82(18) . . ?

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
C4 N1 C1 C2 -0.21(16) . . . . ?
C15 N1 C1 C2 179.24(13) . . . . ?
C4 N1 C1 C5 177.55(14) . . . . ?
C15 N1 C1 C5 -3.0(2) . . . . ?
N1 C1 C2 C3 0.17(16) . . . . ?
C5 C1 C2 C3 -177.34(15) . . . . ?
N1 C1 C2 C9 174.62(13) . . . . ?
C5 C1 C2 C9 -2.9(3) . . . . ?
C1 C2 C3 C4 -0.07(16) . . . . ?
C9 C2 C3 C4 -174.34(13) . . . . ?
C1 C2 C3 C7 -172.64(14) . . . . ?
C9 C2 C3 C7 13.1(2) . . . . ?
C1 N1 C4 C3 0.16(16) . . . . ?
C15 N1 C4 C3 -179.28(13) . . . . ?
C1 N1 C4 C6 175.85(13) . . . . ?
C15 N1 C4 C6 -3.6(2) . . . . ?
C2 C3 C4 N1 -0.06(15) . . . . ?
C7 C3 C4 N1 172.90(13) . . . . ?
C2 C3 C4 C6 -175.26(15) . . . . ?
C7 C3 C4 C6 -2.3(2) . . . . ?
C4 C3 C7 O1 30.9(2) . . . . ?
C2 C3 C7 O1 -157.66(16) . . . . ?
C4 C3 C7 C8 -146.44(15) . . . . ?
C2 C3 C7 C8 25.0(2) . . . . ?
C1 C2 C9 C10 -119.09(18) . . . . ?
C3 C2 C9 C10 54.2(2) . . . . ?
C1 C2 C9 C14 60.4(2) . . . . ?
C3 C2 C9 C14 -126.31(17) . . . . ?
C14 C9 C10 C11 0.3(3) . . . . ?
C2 C9 C10 C11 179.79(17) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C9 -0.5(3) . . . . ?
C10 C9 C14 C13 0.4(2) . . . . ?
C2 C9 C14 C13 -179.06(15) . . . . ?
C4 N1 C15 C16 95.00(19) . . . . ?
C1 N1 C15 C16 -84.4(2) . . . . ?
N1 C15 C16 C17 109.1(2) . . . . ?
N1 C15 C16 O2 -68.9(2) . . . . ?
O2 C16 C17 C18 -1.3(2) . . . . ?
C15 C16 C17 C18 -179.45(18) . . . . ?
C16 C17 C18 C19 1.0(3) . . . . ?
C17 C18 C19 O2 -0.4(3) . . . . ?
C17 C16 O2 C19 1.1(2) . . . . ?
C15 C16 O2 C19 179.55(15) . . . . ?
C18 C19 O2 C16 -0.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.029
_database_code_depnum_ccdc_archive 'CCDC 964609'
