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

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#                                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.
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#  fide research purposes only. It may contain copyright material
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data_feh02

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H19 N O'
_chemical_formula_weight         229.31

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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   5.79405(11)
_cell_length_b                   10.39092(18)
_cell_length_c                   22.3131(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1343.37(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.547
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3105
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.96
_diffrn_reflns_theta_max         61.62
_reflns_number_total             2011
_reflns_number_gt                1923
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0612P)²+0.0936P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_number_reflns         2011
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
C1 C -0.8031(3) -0.32493(17) -0.06496(8) 0.0265(4) Uani 1 1 d . . .
H1 H -0.8632 -0.3437 -0.0249 0.032 Uiso 1 1 calc R . .
C2 C -0.9247(4) -0.20601(16) -0.08897(8) 0.0297(4) Uani 1 1 d . . .
H2A H -0.8635 -0.1845 -0.1282 0.036 Uiso 1 1 calc R . .
H2B H -1.0883 -0.2235 -0.0933 0.036 Uiso 1 1 calc R . .
C3 C -0.9699(4) 0.02794(17) -0.07256(9) 0.0345(5) Uani 1 1 d . . .
H3 H -0.9049 0.0385 -0.1128 0.041 Uiso 1 1 calc R . .
C4 C -0.8809(4) 0.1350(2) -0.03316(11) 0.0519(6) Uani 1 1 d . . .
H4A H -0.9459 0.1268 0.0062 0.078 Uiso 1 1 calc R . .
H4B H -0.9245 0.2165 -0.0500 0.078 Uiso 1 1 calc R . .
H4C H -0.7158 0.1299 -0.0307 0.078 Uiso 1 1 calc R . .
C5 C -1.2291(4) 0.0325(2) -0.07692(12) 0.0530(6) Uani 1 1 d . . .
H5A H -1.2817 -0.0348 -0.1030 0.079 Uiso 1 1 calc R . .
H5B H -1.2759 0.1144 -0.0927 0.079 Uiso 1 1 calc R . .
H5C H -1.2949 0.0208 -0.0378 0.079 Uiso 1 1 calc R . .
C11 C -0.8506(3) -0.43942(17) -0.10512(7) 0.0258(4) Uani 1 1 d . . .
C12 C -0.6970(3) -0.47695(18) -0.14840(7) 0.0284(4) Uani 1 1 d . . .
H12 H -0.5569 -0.4340 -0.1519 0.034 Uiso 1 1 calc R . .
C13 C -0.7471(3) -0.57993(18) -0.18800(8) 0.0297(4) Uani 1 1 d . . .
C14 C -0.5941(4) -0.6153(2) -0.23508(9) 0.0411(5) Uani 1 1 d . . .
H14 H -0.4578 -0.5695 -0.2407 0.049 Uiso 1 1 calc R . .
C15 C -0.6460(4) -0.7159(2) -0.27196(9) 0.0496(6) Uani 1 1 d . . .
H15 H -0.5455 -0.7376 -0.3028 0.060 Uiso 1 1 calc R . .
C16 C -0.8489(4) -0.7866(2) -0.26382(10) 0.0459(6) Uani 1 1 d . . .
H16 H -0.8793 -0.8567 -0.2885 0.055 Uiso 1 1 calc R . .
C17 C -1.0033(4) -0.75384(19) -0.21998(9) 0.0391(5) Uani 1 1 d . . .
H17 H -1.1387 -0.8009 -0.2155 0.047 Uiso 1 1 calc R . .
C18 C -0.9574(3) -0.64821(17) -0.18138(8) 0.0304(4) Uani 1 1 d . . .
C19 C -1.1135(3) -0.60790(18) -0.13647(8) 0.0321(4) Uani 1 1 d . . .
H19 H -1.2524 -0.6515 -0.1315 0.038 Uiso 1 1 calc R . .
C20 C -1.0626(3) -0.50517(17) -0.10003(8) 0.0304(4) Uani 1 1 d . . .
H20 H -1.1697 -0.4786 -0.0716 0.036 Uiso 1 1 calc R . .
N1 N -0.8911(3) -0.09690(13) -0.04793(7) 0.0289(4) Uani 1 1 d . . .
H1A H -0.734(4) -0.0913(19) -0.0432(8) 0.035 Uiso 1 1 d . . .
O1 O -0.5648(2) -0.29615(11) -0.06011(5) 0.0314(3) Uani 1 1 d . . .
H1B H -0.5102 -0.3344 -0.0313 0.047 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
C1 0.0292(10) 0.0262(9) 0.0240(8) -0.0019(7) 0.0011(7) 0.0008(7)
C2 0.0376(11) 0.0251(9) 0.0264(9) -0.0014(7) -0.0017(7) 0.0028(8)
C3 0.0423(11) 0.0233(10) 0.0380(10) 0.0050(8) -0.0006(9) 0.0038(8)
C4 0.0640(15) 0.0254(10) 0.0663(15) -0.0025(10) -0.0183(13) 0.0059(10)
C5 0.0478(14) 0.0366(12) 0.0745(16) 0.0112(11) -0.0090(12) 0.0090(10)
C11 0.0314(10) 0.0243(9) 0.0218(8) 0.0015(7) -0.0032(7) 0.0027(7)
C12 0.0289(10) 0.0273(10) 0.0291(9) -0.0015(8) 0.0007(8) -0.0010(8)
C13 0.0333(10) 0.0297(10) 0.0262(9) -0.0033(8) -0.0050(7) 0.0066(8)
C14 0.0374(11) 0.0478(12) 0.0380(10) -0.0111(10) 0.0026(9) 0.0042(10)
C15 0.0521(14) 0.0576(14) 0.0391(11) -0.0216(11) -0.0012(10) 0.0114(11)
C16 0.0549(14) 0.0403(11) 0.0427(11) -0.0177(10) -0.0133(11) 0.0103(10)
C17 0.0445(12) 0.0306(10) 0.0420(11) -0.0065(9) -0.0128(10) 0.0005(9)
C18 0.0354(10) 0.0253(9) 0.0305(9) -0.0009(8) -0.0084(8) 0.0035(8)
C19 0.0323(10) 0.0287(10) 0.0352(10) 0.0007(8) -0.0014(8) -0.0046(9)
C20 0.0313(10) 0.0300(9) 0.0299(9) 0.0021(8) 0.0024(8) 0.0020(8)
N1 0.0329(8) 0.0214(7) 0.0324(8) 0.0003(6) -0.0005(7) 0.0024(6)
O1 0.0328(7) 0.0304(7) 0.0310(7) -0.0031(5) -0.0049(6) 0.0003(6)

_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 O1 1.417(2) . ?
C1 C11 1.515(2) . ?
C1 C2 1.520(2) . ?
C2 N1 1.470(2) . ?
C3 N1 1.481(2) . ?
C3 C5 1.506(3) . ?
C3 C4 1.509(3) . ?
C11 C12 1.370(2) . ?
C11 C20 1.410(3) . ?
C12 C13 1.418(3) . ?
C13 C18 1.418(3) . ?
C13 C14 1.423(3) . ?
C14 C15 1.364(3) . ?
C15 C16 1.398(3) . ?
C16 C17 1.369(3) . ?
C17 C18 1.420(3) . ?
C18 C19 1.413(3) . ?
C19 C20 1.374(3) . ?

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
O1 C1 C11 112.83(14) . . ?
O1 C1 C2 107.89(15) . . ?
C11 C1 C2 110.23(14) . . ?
N1 C2 C1 110.24(14) . . ?
N1 C3 C5 111.03(17) . . ?
N1 C3 C4 108.94(16) . . ?
C5 C3 C4 110.81(19) . . ?
C12 C11 C20 118.99(16) . . ?
C12 C11 C1 121.52(17) . . ?
C20 C11 C1 119.41(16) . . ?
C11 C12 C13 121.42(18) . . ?
C18 C13 C12 119.26(17) . . ?
C18 C13 C14 118.91(17) . . ?
C12 C13 C14 121.82(18) . . ?
C15 C14 C13 120.4(2) . . ?
C14 C15 C16 120.7(2) . . ?
C17 C16 C15 120.77(19) . . ?
C16 C17 C18 120.2(2) . . ?
C19 C18 C13 118.40(16) . . ?
C19 C18 C17 122.63(19) . . ?
C13 C18 C17 118.98(18) . . ?
C20 C19 C18 120.83(17) . . ?
C19 C20 C11 121.04(17) . . ?
C2 N1 C3 113.80(14) . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        61.62
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.033
_database_code_depnum_ccdc_archive 'CCDC 994083'
