# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009

data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'D Tanner'
'Charlotte H Gotfredsen'
'Pernille Harris'
'Masood Hosseini'
'M Sundaram Shanmugham'
'Paulo Vital'

_publ_contact_author_name        'D Tanner'
_publ_contact_author_email       DT@KEMI.DTU.DK

_publ_section_title              
;
Polycyclic Alkaloids via Transannular Mannich
Reactions
;

# Attachment 'mscy02m_final.cif'

data_mscy02m
_database_code_depnum_ccdc_archive 'CCDC 714338'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H29 N1 O4'
_chemical_formula_weight         311.42

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6851(7)
_cell_length_b                   10.6061(12)
_cell_length_c                   14.1542(16)
_cell_angle_alpha                93.957(2)
_cell_angle_beta                 91.847(2)
_cell_angle_gamma                96.174(2)
_cell_volume                     845.80(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2216
_cell_measurement_theta_min      2.887
_cell_measurement_theta_max      27.207

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             850
_exptl_absorpt_coefficient_mu    0.086
_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      120(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  'Bruker SMART platform ccd'
_diffrn_measurement_method       'profile data from \w/2\q scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11580
_diffrn_reflns_av_R_equivalents  0.1283
_diffrn_reflns_av_sigmaI/netI    0.1282
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.44
_diffrn_reflns_theta_max         28.02
_reflns_number_total             4082
_reflns_number_gt                2593
_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 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^)+(0.1024P)^2^+0.0000P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4082
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1175
_refine_ls_R_factor_gt           0.0678
_refine_ls_wR_factor_ref         0.1839
_refine_ls_wR_factor_gt          0.1484
_refine_ls_goodness_of_fit_ref   0.873
_refine_ls_restrained_S_all      0.873
_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 0.8929(3) 1.02752(19) 0.28325(15) 0.0180(4) Uani 1 1 d . . .
C2 C 0.9008(4) 0.9530(2) 0.36620(18) 0.0204(5) Uani 1 1 d . . .
H2A H 0.7559 0.8919 0.3641 0.025 Uiso 1 1 calc R . .
H2B H 0.8970 1.0113 0.4237 0.025 Uiso 1 1 calc R . .
C3 C 1.1156(4) 0.8789(2) 0.37591(19) 0.0242(6) Uani 1 1 d . . .
H3A H 1.2581 0.9406 0.3898 0.029 Uiso 1 1 calc R . .
H3B H 1.0950 0.8269 0.4311 0.029 Uiso 1 1 calc R . .
C4 C 1.1605(4) 0.7921(2) 0.29011(19) 0.0227(6) Uani 1 1 d . . .
H4A H 1.1791 0.8444 0.2350 0.027 Uiso 1 1 calc R . .
H4B H 1.3130 0.7576 0.3017 0.027 Uiso 1 1 calc R . .
C5 C 0.9749(4) 0.6821(2) 0.26349(18) 0.0203(5) Uani 1 1 d . . .
O5 O 0.7973(3) 0.66245(17) 0.30797(13) 0.0274(5) Uani 1 1 d . . .
C6 C 1.0250(4) 0.5972(2) 0.17806(19) 0.0231(6) Uani 1 1 d . . .
H6A H 1.1222 0.5315 0.1991 0.028 Uiso 1 1 calc R . .
H6B H 1.1198 0.6489 0.1343 0.028 Uiso 1 1 calc R . .
C7 C 0.8050(5) 0.5314(2) 0.12413(19) 0.0228(6) Uani 1 1 d . . .
H7A H 0.7087 0.4802 0.1677 0.027 Uiso 1 1 calc R . .
H7B H 0.8534 0.4727 0.0727 0.027 Uiso 1 1 calc R . .
C8 C 0.6538(4) 0.6253(2) 0.08134(18) 0.0186(5) Uani 1 1 d . . .
H8A H 0.6196 0.6891 0.1320 0.022 Uiso 1 1 calc R . .
H8B H 0.5009 0.5788 0.0573 0.022 Uiso 1 1 calc R . .
C9 C 0.7687(4) 0.6949(2) 0.00052(18) 0.0193(5) Uani 1 1 d . . .
H9A H 0.7808 0.6332 -0.0544 0.023 Uiso 1 1 calc R . .
H9B H 0.9311 0.7317 0.0212 0.023 Uiso 1 1 calc R . .
C10 C 0.6267(4) 0.8012(2) -0.03007(17) 0.0195(5) Uani 1 1 d . . .
H10A H 0.7193 0.8530 -0.0745 0.023 Uiso 1 1 calc R . .
H10B H 0.4776 0.7634 -0.0636 0.023 Uiso 1 1 calc R . .
C11 C 0.5704(4) 0.8851(2) 0.05443(17) 0.0148(5) Uani 1 1 d . . .
O11 O 0.3665(3) 0.89384(15) 0.07582(12) 0.0185(4) Uani 1 1 d . . .
C12 C 0.7741(4) 0.9550(2) 0.11423(17) 0.0162(5) Uani 1 1 d . . .
H12A H 0.8370 1.0315 0.0829 0.019 Uiso 1 1 calc R . .
H12B H 0.9025 0.8995 0.1194 0.019 Uiso 1 1 calc R . .
C13 C 0.6981(4) 0.9947(2) 0.21298(18) 0.0190(5) Uani 1 1 d . . .
H13A H 0.6076 1.0689 0.2089 0.023 Uiso 1 1 calc R . .
H13B H 0.5902 0.9243 0.2353 0.023 Uiso 1 1 calc R . .
C14 C 1.0113(4) 1.1453(2) 0.28107(17) 0.0166(5) Uani 1 1 d . . .
O14 O 0.9784(3) 1.21774(16) 0.21999(13) 0.0213(4) Uani 1 1 d . . .
O15 O 1.1690(3) 1.16986(15) 0.35498(12) 0.0200(4) Uani 1 1 d . . .
C16 C 1.2957(4) 1.2984(2) 0.37642(18) 0.0177(5) Uani 1 1 d . . .
C17 C 1.4436(4) 1.3398(2) 0.29413(19) 0.0214(6) Uani 1 1 d . . .
H17A H 1.5541 1.2771 0.2791 0.032 Uiso 1 1 calc R . .
H17B H 1.5328 1.4228 0.3116 0.032 Uiso 1 1 calc R . .
H17C H 1.3393 1.3460 0.2386 0.032 Uiso 1 1 calc R . .
C18 C 1.4520(5) 1.2804(3) 0.4613(2) 0.0284(6) Uani 1 1 d . . .
H18A H 1.3534 1.2548 0.5137 0.043 Uiso 1 1 calc R . .
H18B H 1.5499 1.3604 0.4805 0.043 Uiso 1 1 calc R . .
H18C H 1.5545 1.2141 0.4450 0.043 Uiso 1 1 calc R . .
C19 C 1.1160(4) 1.3900(3) 0.4010(2) 0.0271(6) Uani 1 1 d . . .
H19A H 1.0021 1.3896 0.3476 0.041 Uiso 1 1 calc R . .
H19B H 1.1976 1.4759 0.4144 0.041 Uiso 1 1 calc R . .
H19C H 1.0323 1.3636 0.4571 0.041 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
N1 0.0176(10) 0.0183(10) 0.0164(11) -0.0017(8) -0.0012(8) -0.0033(8)
C2 0.0203(12) 0.0191(12) 0.0196(13) -0.0011(10) 0.0021(10) -0.0066(9)
C3 0.0216(12) 0.0232(13) 0.0257(15) 0.0044(11) -0.0041(11) -0.0066(10)
C4 0.0168(11) 0.0234(13) 0.0282(15) 0.0068(11) 0.0017(10) -0.0006(10)
C5 0.0213(12) 0.0184(12) 0.0219(14) 0.0051(10) 0.0036(10) 0.0021(10)
O5 0.0281(10) 0.0267(10) 0.0253(11) -0.0016(8) 0.0118(8) -0.0068(8)
C6 0.0235(12) 0.0245(13) 0.0229(14) 0.0025(11) 0.0041(10) 0.0089(10)
C7 0.0313(13) 0.0134(12) 0.0238(14) -0.0014(10) 0.0107(11) 0.0023(10)
C8 0.0182(11) 0.0151(11) 0.0212(13) -0.0042(10) 0.0062(10) -0.0020(9)
C9 0.0212(12) 0.0172(12) 0.0189(13) -0.0036(10) 0.0038(10) 0.0012(9)
C10 0.0211(12) 0.0190(12) 0.0174(13) -0.0043(10) -0.0027(10) 0.0028(10)
C11 0.0163(11) 0.0126(11) 0.0156(12) 0.0027(9) 0.0009(9) 0.0007(9)
O11 0.0125(8) 0.0204(9) 0.0223(10) 0.0005(7) 0.0004(7) 0.0007(6)
C12 0.0122(11) 0.0166(11) 0.0188(13) -0.0027(9) 0.0007(9) -0.0006(9)
C13 0.0144(11) 0.0203(12) 0.0199(13) -0.0059(10) 0.0000(9) -0.0050(9)
C14 0.0128(11) 0.0198(12) 0.0159(12) -0.0038(10) 0.0023(9) -0.0014(9)
O14 0.0213(9) 0.0202(9) 0.0220(10) 0.0031(7) -0.0022(7) -0.0003(7)
O15 0.0202(8) 0.0156(8) 0.0217(9) 0.0014(7) -0.0067(7) -0.0067(7)
C16 0.0131(11) 0.0144(11) 0.0231(13) -0.0040(9) 0.0021(9) -0.0066(9)
C17 0.0148(11) 0.0203(12) 0.0281(15) -0.0006(10) 0.0054(10) -0.0022(9)
C18 0.0229(13) 0.0297(15) 0.0289(16) 0.0018(12) -0.0075(11) -0.0112(11)
C19 0.0170(12) 0.0273(14) 0.0341(16) -0.0111(12) 0.0058(11) -0.0037(10)

_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 C14 1.357(3) . ?
N1 C13 1.461(3) . ?
N1 C2 1.462(3) . ?
C2 C3 1.529(4) . ?
C3 C4 1.518(4) . ?
C4 C5 1.505(3) . ?
C5 O5 1.214(3) . ?
C5 C6 1.510(4) . ?
C6 C7 1.520(4) . ?
C7 C8 1.527(4) . ?
C8 C9 1.530(3) . ?
C9 C10 1.533(3) . ?
C10 C11 1.504(3) . ?
C11 O11 1.219(3) . ?
C11 C12 1.508(3) . ?
C12 C13 1.521(3) . ?
C14 O14 1.218(3) . ?
C14 O15 1.348(3) . ?
O15 C16 1.479(3) . ?
C16 C18 1.507(4) . ?
C16 C19 1.516(3) . ?
C16 C17 1.520(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
C14 N1 C13 116.0(2) . . ?
C14 N1 C2 122.7(2) . . ?
C13 N1 C2 118.44(19) . . ?
N1 C2 C3 115.7(2) . . ?
C4 C3 C2 115.5(2) . . ?
C5 C4 C3 116.8(2) . . ?
O5 C5 C4 122.3(2) . . ?
O5 C5 C6 122.2(2) . . ?
C4 C5 C6 115.6(2) . . ?
C5 C6 C7 114.4(2) . . ?
C6 C7 C8 112.5(2) . . ?
C7 C8 C9 114.14(19) . . ?
C8 C9 C10 111.91(19) . . ?
C11 C10 C9 110.8(2) . . ?
O11 C11 C10 121.3(2) . . ?
O11 C11 C12 120.7(2) . . ?
C10 C11 C12 118.06(19) . . ?
C11 C12 C13 111.50(18) . . ?
N1 C13 C12 114.63(19) . . ?
O14 C14 O15 125.3(2) . . ?
O14 C14 N1 124.0(2) . . ?
O15 C14 N1 110.7(2) . . ?
C14 O15 C16 121.08(18) . . ?
O15 C16 C18 102.51(19) . . ?
O15 C16 C19 108.65(18) . . ?
C18 C16 C19 111.4(2) . . ?
O15 C16 C17 111.18(19) . . ?
C18 C16 C17 110.8(2) . . ?
C19 C16 C17 111.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.02
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.075