# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global

_journal_coden_Cambridge         177
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Chiou, Wen-Hua'
'Chen, Guei-Tang'
'Kao, Chien-Lun'
'Gao, Yu-Kai'

_publ_contact_author_name        'Prof. Wen-Hua Chiou'
_publ_contact_author_email       wchiou@dragon.nchu.edu.tw

_publ_section_title              
;
Syntheses of (-)-Pelletierine and
(-)-Homopipecolic Acid.
;

# Attachment '- 4_KCATAM.cif'

data_kcatam
_database_code_depnum_ccdc_archive 'CCDC 855622'
#TrackingRef '- 4_KCATAM.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C7 H14 N O, C4 H5 O6'
_chemical_formula_sum            'C11 H19 N O7'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      297(2)
_chemical_formula_weight         277.27

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   'P 21'
_symmetry_int_tables_number      4
_chemical_absolute_configuration unk

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

_cell_length_a                   7.1563(10)
_cell_length_b                   8.3628(12)
_cell_length_c                   10.5833(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.637(2)
_cell_angle_gamma                90.00
_cell_volume                     626.19(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      1.95
_cell_measurement_theta_max      25.98
_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    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.96400
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_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_reflns_number            3552
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         25.98
_reflns_number_total             2243
_reflns_number_gt                2179
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.0733P)^2^+0.0392P] 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       0.054(8)
_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   0.4(9)
_refine_ls_number_reflns         2243
_refine_ls_number_parameters     193
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.002
_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
N N -0.6150(2) 0.34485(18) -0.23698(13) 0.0272(3) Uani 1 1 d . . .
H0A H -0.716(3) 0.394(3) -0.206(2) 0.034(5) Uiso 1 1 d . . .
H0B H -0.504(4) 0.375(3) -0.195(2) 0.046(6) Uiso 1 1 d . . .
O1 O -0.29959(19) 0.09869(19) -0.25604(15) 0.0458(4) Uani 1 1 d . . .
H1A H -0.3072 0.0169 -0.2144 0.069 Uiso 1 1 calc R . .
C1 C -0.6330(2) 0.1679(2) -0.25218(16) 0.0303(4) Uani 1 1 d . . .
H1B H -0.6110 0.1136 -0.1692 0.036 Uiso 1 1 calc R . .
C2 C -0.8287(3) 0.1335(2) -0.32227(17) 0.0358(4) Uani 1 1 d . . .
H2A H -0.9218 0.1719 -0.2717 0.043 Uiso 1 1 calc R . .
H2B H -0.8449 0.0188 -0.3324 0.043 Uiso 1 1 calc R . .
C3 C -0.8626(3) 0.2128(3) -0.45334(18) 0.0433(5) Uani 1 1 d . . .
H3A H -0.7968 0.1531 -0.5118 0.052 Uiso 1 1 calc R . .
H3B H -0.9966 0.2101 -0.4862 0.052 Uiso 1 1 calc R . .
C4 C -0.7947(3) 0.3847(3) -0.44781(18) 0.0407(4) Uani 1 1 d . . .
H4B H -0.8834 0.4508 -0.4104 0.049 Uiso 1 1 calc R . .
H4C H -0.7906 0.4229 -0.5339 0.049 Uiso 1 1 calc R . .
C5 C -0.6001(2) 0.4000(2) -0.36923(17) 0.0331(4) Uani 1 1 d . . .
H5B H -0.5537 0.5103 -0.3692 0.040 Uiso 1 1 calc R . .
C6 C -0.4561(3) 0.2828(3) -0.40780(18) 0.0423(5) Uani 1 1 d . . .
H6A H -0.3292 0.3257 -0.3874 0.051 Uiso 1 1 calc R . .
H6B H -0.4817 0.2614 -0.4988 0.051 Uiso 1 1 calc R . .
C7 C -0.4763(3) 0.1301(2) -0.33169(18) 0.0353(4) Uani 1 1 d . . .
H7A H -0.5136 0.0405 -0.3896 0.042 Uiso 1 1 calc R . .
O2 O -0.29016(19) 0.5220(2) -0.15207(17) 0.0481(4) Uani 1 1 d . . .
O3 O -0.30741(17) 0.77208(19) -0.22233(14) 0.0427(4) Uani 1 1 d . . .
O4 O 0.07057(18) 0.49509(17) -0.16201(14) 0.0365(3) Uani 1 1 d . . .
H4A H 0.007(4) 0.445(3) -0.127(2) 0.041(7) Uiso 1 1 d . . .
O5 O 0.05687(17) 0.73382(19) 0.03296(11) 0.0390(3) Uani 1 1 d . . .
H5A H 0.163(4) 0.708(3) 0.076(3) 0.050(7) Uiso 1 1 d . . .
O6 O 0.41596(18) 0.7426(2) -0.00160(13) 0.0531(4) Uani 1 1 d . . .
O7 O 0.34608(17) 0.77616(19) -0.21083(12) 0.0391(3) Uani 1 1 d . . .
H7B H 0.469(5) 0.768(6) -0.208(4) 0.093(11) Uiso 1 1 d . . .
C8 C -0.2202(2) 0.6457(2) -0.18490(16) 0.0304(4) Uani 1 1 d . . .
C9 C -0.0072(2) 0.6476(2) -0.18590(15) 0.0269(3) Uani 1 1 d . . .
H9A H 0.0144 0.6800 -0.2715 0.032 Uiso 1 1 calc R . .
C10 C 0.0930(2) 0.7674(2) -0.09093(15) 0.0284(3) Uani 1 1 d . . .
H10A H 0.0464 0.8749 -0.1151 0.034 Uiso 1 1 calc R . .
C11 C 0.3036(2) 0.7610(2) -0.09591(16) 0.0308(4) Uani 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
N 0.0244(7) 0.0283(8) 0.0289(7) -0.0032(5) 0.0037(5) 0.0009(5)
O1 0.0342(7) 0.0404(8) 0.0617(9) -0.0015(7) 0.0041(6) 0.0059(6)
C1 0.0310(8) 0.0279(9) 0.0321(8) 0.0013(7) 0.0049(6) -0.0005(7)
C2 0.0327(9) 0.0335(10) 0.0402(9) -0.0004(7) 0.0019(7) -0.0052(7)
C3 0.0426(10) 0.0506(12) 0.0336(9) -0.0050(8) -0.0048(7) -0.0003(9)
C4 0.0450(10) 0.0440(11) 0.0321(9) 0.0069(8) 0.0020(7) 0.0063(9)
C5 0.0369(9) 0.0292(9) 0.0349(9) 0.0021(7) 0.0110(7) 0.0010(7)
C6 0.0441(10) 0.0449(12) 0.0416(9) 0.0004(8) 0.0189(8) 0.0037(8)
C7 0.0338(9) 0.0329(10) 0.0402(9) -0.0060(7) 0.0085(7) 0.0036(7)
O2 0.0268(6) 0.0410(8) 0.0756(10) 0.0049(7) 0.0044(6) -0.0073(6)
O3 0.0253(6) 0.0451(9) 0.0581(8) 0.0117(7) 0.0075(5) 0.0037(6)
O4 0.0305(6) 0.0291(7) 0.0530(8) -0.0012(6) 0.0163(6) 0.0008(6)
O5 0.0293(6) 0.0585(9) 0.0301(6) -0.0097(6) 0.0071(5) -0.0016(6)
O6 0.0297(6) 0.0920(13) 0.0354(6) -0.0073(8) -0.0022(5) 0.0055(8)
O7 0.0241(6) 0.0546(9) 0.0397(6) 0.0114(6) 0.0075(5) 0.0007(6)
C8 0.0223(7) 0.0365(9) 0.0319(7) -0.0028(7) 0.0029(6) -0.0030(7)
C9 0.0230(7) 0.0316(9) 0.0267(7) -0.0011(6) 0.0057(5) 0.0005(6)
C10 0.0231(7) 0.0294(8) 0.0329(7) -0.0029(7) 0.0049(6) 0.0001(6)
C11 0.0239(7) 0.0311(8) 0.0373(8) -0.0038(7) 0.0040(6) -0.0008(7)

_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
N C1 1.492(2) . ?
N C5 1.493(2) . ?
N H0A 0.93(2) . ?
N H0B 0.89(3) . ?
O1 C7 1.416(2) . ?
O1 H1A 0.8200 . ?
C1 C2 1.511(2) . ?
C1 C7 1.533(2) . ?
C1 H1B 0.9800 . ?
C2 C3 1.524(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.515(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.517(3) . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
C5 C6 1.522(3) . ?
C5 H5B 0.9800 . ?
C6 C7 1.528(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9800 . ?
O2 C8 1.222(3) . ?
O3 C8 1.261(2) . ?
O4 C9 1.399(2) . ?
O4 H4A 0.75(3) . ?
O5 C10 1.402(2) . ?
O5 H5A 0.85(3) . ?
O6 C11 1.194(2) . ?
O7 C11 1.303(2) . ?
O7 H7B 0.88(4) . ?
C8 C9 1.526(2) . ?
C9 C10 1.520(2) . ?
C9 H9A 0.9800 . ?
C10 C11 1.516(2) . ?
C10 H10A 0.9800 . ?

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 N C5 102.86(13) . . ?
C1 N H0A 114.5(15) . . ?
C5 N H0A 111.3(14) . . ?
C1 N H0B 113.0(18) . . ?
C5 N H0B 101.6(16) . . ?
H0A N H0B 112(2) . . ?
C7 O1 H1A 109.5 . . ?
N C1 C2 107.49(15) . . ?
N C1 C7 101.85(14) . . ?
C2 C1 C7 113.08(15) . . ?
N C1 H1B 111.3 . . ?
C2 C1 H1B 111.3 . . ?
C7 C1 H1B 111.3 . . ?
C1 C2 C3 111.91(16) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C2 111.81(16) . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C3 C4 C5 111.35(16) . . ?
C3 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 H4C 109.4 . . ?
C5 C4 H4C 109.4 . . ?
H4B C4 H4C 108.0 . . ?
N C5 C4 107.38(14) . . ?
N C5 C6 101.48(14) . . ?
C4 C5 C6 113.67(17) . . ?
N C5 H5B 111.3 . . ?
C4 C5 H5B 111.3 . . ?
C6 C5 H5B 111.3 . . ?
C5 C6 C7 106.00(14) . . ?
C5 C6 H6A 110.5 . . ?
C7 C6 H6A 110.5 . . ?
C5 C6 H6B 110.5 . . ?
C7 C6 H6B 110.5 . . ?
H6A C6 H6B 108.7 . . ?
O1 C7 C1 113.13(15) . . ?
O1 C7 C6 107.84(16) . . ?
C1 C7 C6 104.59(15) . . ?
O1 C7 H7A 110.4 . . ?
C1 C7 H7A 110.4 . . ?
C6 C7 H7A 110.4 . . ?
C9 O4 H4A 110(2) . . ?
C10 O5 H5A 106.3(17) . . ?
C11 O7 H7B 109(2) . . ?
O2 C8 O3 126.48(15) . . ?
O2 C8 C9 117.61(16) . . ?
O3 C8 C9 115.88(15) . . ?
O4 C9 C10 110.23(14) . . ?
O4 C9 C8 111.06(15) . . ?
C10 C9 C8 112.03(13) . . ?
O4 C9 H9A 107.8 . . ?
C10 C9 H9A 107.8 . . ?
C8 C9 H9A 107.8 . . ?
O5 C10 C11 110.45(13) . . ?
O5 C10 C9 110.57(14) . . ?
C11 C10 C9 109.06(13) . . ?
O5 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
O6 C11 O7 124.78(15) . . ?
O6 C11 C10 121.56(15) . . ?
O7 C11 C10 113.66(13) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.98
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.056