# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2009


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Gonzalo Blay'
_publ_contact_author_email       Gonzalo.Blay@uv.es
_publ_author_name                J.R.Pedro

data_ja489
_database_code_depnum_ccdc_archive 'CCDC 734711'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H25 N O2'
_chemical_formula_weight         335.43

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   P21

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

_cell_length_a                   9.9740(3)
_cell_length_b                   8.8110(3)
_cell_length_c                   12.1490(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.2480(10)
_cell_angle_gamma                90
_cell_volume                     1013.97(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.099
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.070
_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     0.71073
_diffrn_radiation_type           MoK\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            8581
_diffrn_reflns_av_R_equivalents  0.0957
_diffrn_reflns_av_sigmaI/netI    0.0988
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         26.74
_reflns_number_total             4178
_reflns_number_gt                2557
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       'HKL DENZO'
_computing_data_reduction        'HKL DENZO and SCALEPACK'
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1126P)^2^+0.0977P] where P=(Fo^2^+2Fc^2^)/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     SHELXL
_refine_ls_extinction_coef       0.025(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(2)
_refine_ls_number_reflns         4178
_refine_ls_number_parameters     252
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.0683
_refine_ls_wR_factor_ref         0.2119
_refine_ls_wR_factor_gt          0.1676
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.003
_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
O1 O 0.5367(3) 0.1342(2) 0.3624(2) 0.0586(6) Uani 1 1 d . . .
O2 O 0.6074(3) 0.3521(2) 0.4622(2) 0.0645(7) Uani 1 1 d . . .
N1 N 0.5106(4) 0.1604(4) 0.5343(3) 0.0665(9) Uani 1 1 d . . .
C1 C 0.5570(3) 0.2257(4) 0.4552(3) 0.0506(8) Uani 1 1 d . . .
C2 C 0.5981(4) 0.1844(4) 0.2741(3) 0.0547(8) Uani 1 1 d . . .
C3 C 0.7407(4) 0.1226(4) 0.3000(3) 0.0617(9) Uani 1 1 d . . .
C4 C 0.8550(4) 0.0682(4) 0.3229(3) 0.0682(10) Uani 1 1 d . . .
C5 C 0.9949(4) -0.0058(5) 0.3532(4) 0.0779(12) Uani 1 1 d . . .
C6 C 0.9822(7) -0.1485(8) 0.2874(8) 0.152(3) Uani 1 1 d . . .
H6A H 1.0730 -0.1966 0.3063 0.161(6) Uiso 1 1 calc R . .
H6B H 0.9486 -0.1268 0.2059 0.161(6) Uiso 1 1 calc R . .
H6C H 0.9170 -0.2148 0.3071 0.161(6) Uiso 1 1 calc R . .
C7 C 1.1027(6) 0.1003(8) 0.3337(7) 0.135(2) Uani 1 1 d . . .
H7A H 1.1927 0.0503 0.3537 0.161(6) Uiso 1 1 calc R . .
H7B H 1.1098 0.1889 0.3812 0.161(6) Uiso 1 1 calc R . .
H7C H 1.0747 0.1298 0.2536 0.161(6) Uiso 1 1 calc R . .
C8 C 1.0381(6) -0.0436(10) 0.4830(6) 0.135(3) Uani 1 1 d . . .
H8A H 1.1291 -0.0916 0.5063 0.161(6) Uiso 1 1 calc R . .
H8B H 0.9698 -0.1110 0.4973 0.161(6) Uiso 1 1 calc R . .
H8C H 1.0425 0.0481 0.5266 0.161(6) Uiso 1 1 calc R . .
C9 C 0.5298(4) 0.2265(4) 0.6484(3) 0.0612(9) Uani 1 1 d . . .
C10 C 0.6592(4) 0.1620(5) 0.7395(3) 0.0670(10) Uani 1 1 d . . .
C11 C 0.7430(5) 0.0498(5) 0.7164(5) 0.0875(13) Uani 1 1 d . . .
H11 H 0.7216 0.0103 0.6419 0.161(6) Uiso 1 1 calc R . .
C12 C 0.8591(7) -0.0045(6) 0.8039(8) 0.121(2) Uani 1 1 d . . .
H12 H 0.9151 -0.0802 0.7875 0.161(6) Uiso 1 1 calc R . .
C13 C 0.8916(7) 0.0522(9) 0.9135(7) 0.127(2) Uani 1 1 d . . .
H13 H 0.9684 0.0135 0.9719 0.161(6) Uiso 1 1 calc R . .
C14 C 0.8124(7) 0.1648(12) 0.9377(5) 0.129(2) Uani 1 1 d . . .
H14 H 0.8352 0.2045 1.0123 0.161(6) Uiso 1 1 calc R . .
C15 C 0.6968(5) 0.2201(8) 0.8501(4) 0.1021(16) Uani 1 1 d . . .
H15 H 0.6436 0.2984 0.8667 0.161(6) Uiso 1 1 calc R . .
C16 C 0.3965(5) 0.2051(6) 0.6806(5) 0.0798(12) Uani 1 1 d . . .
C17 C 0.4980(3) 0.1392(4) 0.1586(3) 0.0571(8) Uani 1 1 d . . .
C18 C 0.3619(4) 0.1981(5) 0.1257(4) 0.0793(12) Uani 1 1 d . . .
H18 H 0.3350 0.2612 0.1765 0.161(6) Uiso 1 1 calc R . .
C19 C 0.2665(5) 0.1648(7) 0.0197(5) 0.0982(14) Uani 1 1 d . . .
H19 H 0.1761 0.2058 -0.0014 0.161(6) Uiso 1 1 calc R . .
C20 C 0.3053(6) 0.0706(7) -0.0550(4) 0.0956(15) Uani 1 1 d . . .
H20 H 0.2406 0.0463 -0.1265 0.161(6) Uiso 1 1 calc R . .
C21 C 0.4376(6) 0.0131(6) -0.0248(4) 0.0919(14) Uani 1 1 d . . .
H21 H 0.4634 -0.0496 -0.0763 0.161(6) Uiso 1 1 calc R . .
C22 C 0.5353(5) 0.0461(4) 0.0817(4) 0.0728(11) Uani 1 1 d . . .
H22 H 0.6258 0.0056 0.1014 0.161(6) Uiso 1 1 calc R . .
H3 H 0.604(3) 0.291(4) 0.276(3) 0.047(8) Uiso 1 1 d . . .
H9 H 0.544(3) 0.336(4) 0.642(3) 0.049(8) Uiso 1 1 d . . .
H16A H 0.406(4) 0.248(5) 0.757(4) 0.080(12) Uiso 1 1 d . . .
H16B H 0.362(5) 0.088(6) 0.680(4) 0.087(13) Uiso 1 1 d . . .
H16C H 0.319(5) 0.249(6) 0.625(4) 0.093(15) Uiso 1 1 d . . .
H1N H 0.484(4) 0.082(5) 0.526(3) 0.064(12) Uiso 1 1 d . . .

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
O1 0.0744(15) 0.0501(12) 0.0597(14) -0.0080(10) 0.0332(12) -0.0091(11)
O2 0.0794(17) 0.0465(12) 0.0758(17) -0.0042(11) 0.0364(14) -0.0087(12)
N1 0.096(2) 0.0430(16) 0.070(2) -0.0078(15) 0.0387(18) -0.0164(16)
C1 0.0487(18) 0.0436(16) 0.062(2) -0.0007(15) 0.0205(16) -0.0008(14)
C2 0.061(2) 0.0485(18) 0.060(2) -0.0002(15) 0.0277(18) -0.0005(14)
C3 0.064(2) 0.0628(19) 0.058(2) -0.0004(16) 0.0186(17) -0.0022(18)
C4 0.065(3) 0.068(2) 0.068(3) -0.0005(18) 0.0154(19) -0.0002(19)
C5 0.053(2) 0.077(2) 0.098(3) -0.002(2) 0.016(2) 0.0055(18)
C6 0.091(4) 0.118(4) 0.253(9) -0.059(5) 0.062(5) 0.013(3)
C7 0.076(3) 0.130(5) 0.207(7) 0.026(5) 0.058(4) 0.003(3)
C8 0.088(4) 0.163(6) 0.140(6) 0.045(5) 0.016(4) 0.031(4)
C9 0.078(2) 0.0519(19) 0.059(2) -0.0068(17) 0.0285(19) -0.0049(17)
C10 0.070(2) 0.065(2) 0.071(3) 0.0004(19) 0.030(2) -0.0131(19)
C11 0.081(3) 0.062(2) 0.118(4) 0.001(2) 0.028(3) -0.002(2)
C12 0.083(4) 0.075(3) 0.189(7) 0.015(4) 0.022(4) 0.001(3)
C13 0.088(4) 0.127(5) 0.143(6) 0.037(5) 0.004(4) -0.025(4)
C14 0.102(4) 0.183(6) 0.090(4) -0.006(5) 0.015(4) -0.017(5)
C15 0.082(3) 0.148(5) 0.073(3) -0.013(3) 0.019(3) 0.003(3)
C16 0.071(3) 0.101(4) 0.072(3) -0.006(3) 0.028(2) 0.007(2)
C17 0.059(2) 0.0552(18) 0.061(2) 0.0062(16) 0.0254(17) 0.0024(16)
C18 0.057(2) 0.099(3) 0.080(3) -0.011(2) 0.019(2) 0.013(2)
C19 0.070(3) 0.126(4) 0.091(4) 0.006(3) 0.013(3) 0.007(3)
C20 0.088(4) 0.121(4) 0.066(3) 0.008(3) 0.005(3) -0.014(3)
C21 0.115(4) 0.103(3) 0.054(3) -0.006(2) 0.021(3) 0.006(3)
C22 0.077(3) 0.076(2) 0.066(3) 0.003(2) 0.024(2) 0.016(2)

_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
O1 C1 1.349(4) . ?
O1 C2 1.460(4) . ?
O2 C1 1.214(4) . ?
N1 C1 1.323(5) . ?
N1 C9 1.459(5) . ?
N1 H1N 0.74(4) . ?
C2 C3 1.462(5) . ?
C2 C17 1.499(5) . ?
C2 H3 0.94(3) . ?
C3 C4 1.186(5) . ?
C4 C5 1.479(6) . ?
C5 C6 1.474(8) . ?
C5 C7 1.499(7) . ?
C5 C8 1.535(8) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C16 1.510(6) . ?
C9 C10 1.523(6) . ?
C9 H9 0.98(4) . ?
C10 C15 1.376(6) . ?
C10 C11 1.379(6) . ?
C11 C12 1.389(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.363(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.357(11) . ?
C13 H13 0.9300 . ?
C14 C15 1.390(9) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.98(5) . ?
C16 H16B 1.09(5) . ?
C16 H16C 0.94(5) . ?
C17 C22 1.379(5) . ?
C17 C18 1.389(5) . ?
C18 C19 1.372(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.352(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(6) . ?
C21 H21 0.9300 . ?
C22 H22 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
C1 O1 C2 116.5(2) . . ?
C1 N1 C9 123.0(3) . . ?
C1 N1 H1N 120(3) . . ?
C9 N1 H1N 116(3) . . ?
O2 C1 N1 125.4(3) . . ?
O2 C1 O1 123.9(3) . . ?
N1 C1 O1 110.7(3) . . ?
O1 C2 C3 109.4(3) . . ?
O1 C2 C17 107.3(3) . . ?
C3 C2 C17 114.9(3) . . ?
O1 C2 H3 108(2) . . ?
C3 C2 H3 109(2) . . ?
C17 C2 H3 108.0(19) . . ?
C4 C3 C2 177.7(4) . . ?
C3 C4 C5 177.4(4) . . ?
C4 C5 C6 109.1(4) . . ?
C4 C5 C7 110.7(4) . . ?
C6 C5 C7 112.9(5) . . ?
C4 C5 C8 106.9(4) . . ?
C6 C5 C8 108.7(6) . . ?
C7 C5 C8 108.3(5) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C16 109.3(3) . . ?
N1 C9 C10 111.7(3) . . ?
C16 C9 C10 112.3(4) . . ?
N1 C9 H9 107.0(19) . . ?
C16 C9 H9 108.0(19) . . ?
C10 C9 H9 108.2(19) . . ?
C15 C10 C11 118.0(4) . . ?
C15 C10 C9 118.7(4) . . ?
C11 C10 C9 123.3(4) . . ?
C10 C11 C12 120.3(5) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.5(6) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 120.2(6) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.4(7) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C10 C15 C14 121.6(6) . . ?
C10 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C9 C16 H16A 112(3) . . ?
C9 C16 H16B 115(3) . . ?
H16A C16 H16B 108(4) . . ?
C9 C16 H16C 111(3) . . ?
H16A C16 H16C 110(4) . . ?
H16B C16 H16C 101(4) . . ?
C22 C17 C18 118.3(3) . . ?
C22 C17 C2 123.3(3) . . ?
C18 C17 C2 118.4(3) . . ?
C19 C18 C17 121.2(4) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 119.6(5) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 120.0(4) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 121.1(5) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C17 C22 C21 119.8(4) . . ?
C17 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.74
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.054