# Supplementary Material (ESI) for ChemComm
# This journal is © The Royal Society of Chemistry 2000
# CCDC Number: 182/1807
  
data_frsad1 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C14 H19 N O2' 
_chemical_formula_weight          233.30 
  
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            Tetragonal 
_symmetry_space_group_name_H-M    P4(1)2(1)2 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, z+1/2' 
 '-y+1/2, x+1/2, z+1/4' 
 'y+1/2, -x+1/2, z+3/4' 
 '-x+1/2, y+1/2, -z+1/4' 
 'x+1/2, -y+1/2, -z+3/4' 
 'y, x, -z' 
 '-y, -x, -z+1/2' 
  
_cell_length_a                    9.4318(2) 
_cell_length_b                    9.4318(2) 
_cell_length_c                    27.9890(8) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      2489.87(10) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     95(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
  
_exptl_crystal_description        octahedra 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.80 
_exptl_crystal_size_mid           0.50 
_exptl_crystal_size_min           0.28 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.245 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1008 
_exptl_absorpt_coefficient_mu     0.083 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.9368 
_exptl_absorpt_correction_T_max   0.9772 
_exptl_absorpt_process_details    'Blessing, Acta Cryst. (1995) A51 33-38.' 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       95(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_%         No 
_diffrn_reflns_number             21320 
_diffrn_reflns_av_R_equivalents   0.0347 
_diffrn_reflns_av_sigmaI/netI     0.0180 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -32 
_diffrn_reflns_limit_l_max        37 
_diffrn_reflns_theta_min          2.28 
_diffrn_reflns_theta_max          28.29 
_reflns_number_total              3070 
_reflns_number_gt                 2830 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection        'Bruker SMART' 
_computing_cell_refinement        'Bruker SMART' 
_computing_data_reduction         'Bruker SHELXTL' 
_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 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^)+(0.0386P)^2^+0.5064P] 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        0.0035(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    -0.2(9) 
_refine_ls_number_reflns          3070 
_refine_ls_number_parameters      231 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0348 
_refine_ls_R_factor_gt            0.0306 
_refine_ls_wR_factor_ref          0.0770 
_refine_ls_wR_factor_gt           0.0747 
_refine_ls_goodness_of_fit_ref    1.039 
_refine_ls_restrained_S_all       1.039 
_refine_ls_shift/su_max           0.001 
_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 0.35408(13) 0.82528(13) 0.98468(4) 0.0222(2) Uani 1 1 d . . . 
H1 H 0.2617(16) 0.8167(16) 0.9692(5) 0.027(4) Uiso 1 1 d . . . 
C2 C 0.33537(14) 0.90299(14) 1.03299(4) 0.0257(3) Uani 1 1 d . . . 
H2B H 0.4123(17) 0.8829(16) 1.0562(5) 0.029(4) Uiso 1 1 d . . . 
H2A H 0.2473(19) 0.8845(18) 1.0496(6) 0.038(4) Uiso 1 1 d . . . 
C3 C 0.35844(13) 1.04563(13) 1.00681(4) 0.0252(2) Uani 1 1 d . . . 
H3A H 0.2642(17) 1.0906(17) 0.9958(6) 0.036(4) Uiso 1 1 d . . . 
H3B H 0.4204(18) 1.1163(18) 1.0227(5) 0.036(4) Uiso 1 1 d . . . 
C4 C 0.42514(12) 0.96396(12) 0.96440(4) 0.0200(2) Uani 1 1 d . . . 
H4 H 0.3959(14) 0.9925(15) 0.9318(5) 0.021(3) Uiso 1 1 d . . . 
C5 C 0.43549(15) 0.68683(13) 0.98337(5) 0.0267(3) Uani 1 1 d . . . 
H5A H 0.5262(17) 0.6994(16) 1.0010(6) 0.031(4) Uiso 1 1 d . . . 
H5B H 0.4576(16) 0.6566(16) 0.9509(5) 0.026(4) Uiso 1 1 d . . . 
H5C H 0.3772(18) 0.6138(19) 0.9984(6) 0.044(4) Uiso 1 1 d . . . 
C6 C 0.58590(12) 0.95607(12) 0.96610(4) 0.0180(2) Uani 1 1 d . . . 
O1 O 0.65631(9) 0.99407(9) 1.00122(3) 0.02323(19) Uani 1 1 d . . . 
N1 N 0.64605(10) 0.90025(10) 0.92693(3) 0.01886(19) Uani 1 1 d . . . 
H15 H 0.5899(17) 0.8763(17) 0.9019(5) 0.032(4) Uiso 1 1 d . . . 
C7 C 0.79742(11) 0.86852(12) 0.92431(4) 0.0185(2) Uani 1 1 d . . . 
H7 H 0.8320(14) 0.8635(14) 0.9572(4) 0.014(3) Uiso 1 1 d . . . 
C8 C 0.81480(13) 0.72093(12) 0.90153(4) 0.0210(2) Uani 1 1 d . . . 
H8A H 0.7854(15) 0.7235(15) 0.8668(5) 0.020(3) Uiso 1 1 d . . . 
H8B H 0.7513(16) 0.6536(16) 0.9199(5) 0.027(4) Uiso 1 1 d . . . 
O2 O 0.95828(9) 0.67410(9) 0.90228(3) 0.02251(18) Uani 1 1 d . . . 
H16 H 0.9810(18) 0.6590(19) 0.9337(6) 0.042(5) Uiso 1 1 d . . . 
C9 C 0.88101(12) 0.98129(12) 0.89787(4) 0.0191(2) Uani 1 1 d . . . 
C10 C 1.02335(13) 1.00315(12) 0.90938(4) 0.0245(2) Uani 1 1 d . . . 
H10 H 1.0673(17) 0.9517(17) 0.9365(5) 0.030(4) Uiso 1 1 d . . . 
C11 C 1.10356(13) 1.10297(13) 0.88451(5) 0.0290(3) Uani 1 1 d . . . 
H11 H 1.200(2) 1.1169(18) 0.8928(6) 0.045(5) Uiso 1 1 d . . . 
C12 C 1.04266(14) 1.18171(13) 0.84803(5) 0.0278(3) Uani 1 1 d . . . 
H12 H 1.0991(17) 1.2510(17) 0.8307(5) 0.031(4) Uiso 1 1 d . . . 
C13 C 0.90148(14) 1.15969(13) 0.83604(4) 0.0255(2) Uani 1 1 d . . . 
H13 H 0.8550(18) 1.2117(17) 0.8097(5) 0.035(4) Uiso 1 1 d . . . 
C14 C 0.82105(13) 1.06038(13) 0.86092(4) 0.0222(2) Uani 1 1 d . . . 
H14 H 0.7204(17) 1.0441(16) 0.8522(5) 0.031(4) 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 
C1 0.0186(5) 0.0252(6) 0.0230(5) 0.0023(5) 0.0001(4) -0.0009(5) 
C2 0.0241(6) 0.0284(6) 0.0245(6) 0.0019(5) 0.0056(5) 0.0035(5) 
C3 0.0250(6) 0.0244(6) 0.0261(6) -0.0008(5) 0.0039(5) 0.0074(5) 
C4 0.0195(5) 0.0203(5) 0.0202(5) 0.0008(4) 0.0008(4) 0.0038(4) 
C5 0.0311(7) 0.0205(6) 0.0284(6) 0.0013(5) 0.0041(5) 0.0007(5) 
C6 0.0204(5) 0.0162(5) 0.0175(5) 0.0024(4) 0.0009(4) 0.0012(4) 
O1 0.0229(4) 0.0272(4) 0.0196(4) -0.0042(3) -0.0012(3) 0.0011(3) 
N1 0.0167(4) 0.0222(5) 0.0177(4) -0.0013(4) -0.0009(4) 0.0008(3) 
C7 0.0157(5) 0.0222(5) 0.0176(5) -0.0013(4) -0.0005(4) 0.0013(4) 
C8 0.0203(5) 0.0199(5) 0.0228(5) -0.0005(4) 0.0033(4) 0.0010(4) 
O2 0.0227(4) 0.0245(4) 0.0203(4) 0.0008(3) 0.0039(3) 0.0057(3) 
C9 0.0184(5) 0.0188(5) 0.0201(5) -0.0040(4) 0.0017(4) 0.0013(4) 
C10 0.0196(6) 0.0206(5) 0.0331(6) -0.0008(5) -0.0030(5) 0.0023(4) 
C11 0.0179(6) 0.0238(6) 0.0451(7) -0.0035(5) 0.0011(5) -0.0009(5) 
C12 0.0275(6) 0.0201(6) 0.0358(6) -0.0013(5) 0.0092(5) -0.0027(5) 
C13 0.0290(6) 0.0221(6) 0.0254(6) 0.0004(5) 0.0025(5) 0.0020(5) 
C14 0.0205(5) 0.0231(6) 0.0229(5) -0.0008(4) -0.0006(4) 0.0007(4) 
  
_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 C5 1.5153(17) . ? 
C1 C2 1.5480(17) . ? 
C1 C4 1.5755(17) . ? 
C1 H1 0.976(15) . ? 
C2 C3 1.5473(18) . ? 
C2 H2B 0.992(16) . ? 
C2 H2A 0.968(18) . ? 
C3 C4 1.5484(16) . ? 
C3 H3A 1.032(17) . ? 
C3 H3B 0.991(17) . ? 
C4 C6 1.5189(16) . ? 
C4 H4 0.990(13) . ? 
C5 H5A 0.994(16) . ? 
C5 H5B 0.976(15) . ? 
C5 H5C 0.977(18) . ? 
C6 O1 1.2390(14) . ? 
C6 N1 1.3421(14) . ? 
N1 C7 1.4606(14) . ? 
N1 H15 0.907(16) . ? 
C7 C9 1.5168(15) . ? 
C7 C8 1.5398(16) . ? 
C7 H7 0.978(13) . ? 
C8 O2 1.4237(14) . ? 
C8 H8A 1.010(14) . ? 
C8 H8B 1.013(15) . ? 
O2 H16 0.918(18) . ? 
C9 C14 1.3949(16) . ? 
C9 C10 1.3960(16) . ? 
C10 C11 1.3941(18) . ? 
C10 H10 0.992(15) . ? 
C11 C12 1.3869(19) . ? 
C11 H11 0.950(19) . ? 
C12 C13 1.3889(19) . ? 
C12 H12 0.973(16) . ? 
C13 C14 1.3920(17) . ? 
C13 H13 0.989(16) . ? 
C14 H14 0.992(16) . ? 
  
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 
C5 C1 C2 119.14(10) . . ? 
C5 C1 C4 119.42(10) . . ? 
C2 C1 C4 88.28(9) . . ? 
C5 C1 H1 111.7(9) . . ? 
C2 C1 H1 108.9(9) . . ? 
C4 C1 H1 106.8(9) . . ? 
C3 C2 C1 88.97(9) . . ? 
C3 C2 H2B 111.9(9) . . ? 
C1 C2 H2B 113.4(9) . . ? 
C3 C2 H2A 120.3(10) . . ? 
C1 C2 H2A 115.6(10) . . ? 
H2B C2 H2A 106.2(13) . . ? 
C2 C3 C4 89.29(9) . . ? 
C2 C3 H3A 112.2(9) . . ? 
C4 C3 H3A 109.0(9) . . ? 
C2 C3 H3B 117.1(9) . . ? 
C4 C3 H3B 116.0(10) . . ? 
H3A C3 H3B 111.4(13) . . ? 
C6 C4 C3 113.95(10) . . ? 
C6 C4 C1 111.88(9) . . ? 
C3 C4 C1 87.94(9) . . ? 
C6 C4 H4 108.7(8) . . ? 
C3 C4 H4 117.3(8) . . ? 
C1 C4 H4 116.0(8) . . ? 
C1 C5 H5A 108.7(9) . . ? 
C1 C5 H5B 112.5(9) . . ? 
H5A C5 H5B 108.3(13) . . ? 
C1 C5 H5C 108.2(10) . . ? 
H5A C5 H5C 110.8(13) . . ? 
H5B C5 H5C 108.4(13) . . ? 
O1 C6 N1 122.34(10) . . ? 
O1 C6 C4 123.07(10) . . ? 
N1 C6 C4 114.56(10) . . ? 
C6 N1 C7 122.31(9) . . ? 
C6 N1 H15 118.8(10) . . ? 
C7 N1 H15 118.7(10) . . ? 
N1 C7 C9 112.89(9) . . ? 
N1 C7 C8 108.07(9) . . ? 
C9 C7 C8 112.12(9) . . ? 
N1 C7 H7 106.8(8) . . ? 
C9 C7 H7 108.7(8) . . ? 
C8 C7 H7 108.1(8) . . ? 
O2 C8 C7 112.06(10) . . ? 
O2 C8 H8A 106.4(8) . . ? 
C7 C8 H8A 110.3(8) . . ? 
O2 C8 H8B 111.1(9) . . ? 
C7 C8 H8B 107.1(8) . . ? 
H8A C8 H8B 109.9(11) . . ? 
C8 O2 H16 106.5(11) . . ? 
C14 C9 C10 118.82(11) . . ? 
C14 C9 C7 121.74(10) . . ? 
C10 C9 C7 119.39(10) . . ? 
C11 C10 C9 120.42(11) . . ? 
C11 C10 H10 119.0(10) . . ? 
C9 C10 H10 120.5(10) . . ? 
C12 C11 C10 120.29(12) . . ? 
C12 C11 H11 120.2(11) . . ? 
C10 C11 H11 119.5(11) . . ? 
C11 C12 C13 119.66(12) . . ? 
C11 C12 H12 120.1(9) . . ? 
C13 C12 H12 120.3(9) . . ? 
C12 C13 C14 120.15(12) . . ? 
C12 C13 H13 122.1(10) . . ? 
C14 C13 H13 117.7(10) . . ? 
C13 C14 C9 120.65(11) . . ? 
C13 C14 H14 120.2(9) . . ? 
C9 C14 H14 119.2(9) . . ? 
  
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 
C1 C2 C3 C4 -17.87(9) . . . . ? 
C2 C3 C4 C1 17.56(9) . . . . ? 
  
_diffrn_measured_fraction_theta_max    0.995 
_diffrn_reflns_theta_full              28.29 
_diffrn_measured_fraction_theta_full   0.995 
_refine_diff_density_max    0.186 
_refine_diff_density_min   -0.135 
_refine_diff_density_rms    0.032 

_publ_requested_journal   'test'