# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2010

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Hiromitsu Takayama'
_publ_contact_author_email       HTAKAYAM@P.CHIBA-U.AC.JP

_publ_section_title              
;
Determination of Absolute Configuration of Trimeric
Indole Alkaloid, Psychotrimine, by First Asymmetric Total Synthesis
;
loop_
_publ_author_name
'Hiromitsu Takayama'
'Takeshi Ito'
'Mariko Kitajima'
'Noriyuki Kogure'
'Yohei Matsuda'
'Nobuaki Takahashi'

# Attachment 'nitrile-13.cif'

data_nitrile13
_database_code_depnum_ccdc_archive 'CCDC 754033'
#TrackingRef 'nitrile-13.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;

_chemical_formula_sum            'C25 H21 Br N2'
_chemical_formula_weight         429.35

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   13.567(3)
_cell_length_b                   11.127(3)
_cell_length_c                   14.395(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.453(3)
_cell_angle_gamma                90.00
_cell_volume                     2008.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173
_cell_measurement_reflns_used    2400
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      24.00

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_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    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    2.059
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5770
_exptl_absorpt_correction_T_max  0.6835
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173
_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 APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            6967
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         24.92
_reflns_number_total             3434
_reflns_number_gt                1999
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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^)+(0.0539P)^2^+2.0484P] 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       Fsqd
_refine_ls_number_reflns         3434
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1059
_refine_ls_wR_factor_gt          0.0996
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
Br1 Br 0.97629(4) 1.20714(5) 0.37658(4) 0.0773(3) Uani 1 1 d . . .
N3 N 1.0800(2) 1.0661(3) 0.2557(2) 0.0345(8) Uani 1 1 d . . .
C22 C 1.2551(3) 1.0571(3) 0.3606(3) 0.0388(10) Uani 1 1 d . . .
C18 C 1.1528(3) 0.8757(4) 0.3586(3) 0.0399(10) Uani 1 1 d . . .
H18 H 1.0894 0.8323 0.3345 0.048 Uiso 1 1 calc R . .
C17 C 1.1593(3) 0.9938(3) 0.3249(3) 0.0314(9) Uani 1 1 d . . .
C19 C 1.2446(3) 0.8285(4) 0.4286(3) 0.0426(10) Uani 1 1 d . . .
H19 H 1.2430 0.7510 0.4521 0.051 Uiso 1 1 calc R . .
C6 C 0.6537(3) 1.0045(3) -0.0983(3) 0.0344(9) Uani 1 1 d . . .
C24 C 0.9740(3) 1.0218(3) 0.1971(3) 0.0312(9) Uani 1 1 d . . .
C8 C 0.7959(3) 1.0750(3) 0.0610(3) 0.0389(10) Uani 1 1 d . . .
H8 H 0.7489 1.0663 0.0936 0.047 Uiso 1 1 calc R . .
C20 C 1.3396(3) 0.8918(4) 0.4656(3) 0.0463(11) Uani 1 1 d . . .
H20 H 1.4002 0.8566 0.5127 0.056 Uiso 1 1 calc R . .
C7 C 0.7605(3) 1.0482(3) -0.0356(3) 0.0347(9) Uani 1 1 d . . .
H7 H 0.8083 1.0580 -0.0672 0.042 Uiso 1 1 calc R . .
C25 C 0.9854(3) 0.9184(4) 0.1348(3) 0.0345(9) Uani 1 1 d . . .
C9 C 0.9164(3) 0.9826(4) 0.2652(3) 0.0383(10) Uani 1 1 d . . .
C23 C 0.9061(3) 1.1184(4) 0.1215(3) 0.0389(10) Uani 1 1 d . . .
H23A H 0.9018 1.1900 0.1583 0.047 Uiso 1 1 calc R . .
H23B H 0.9412 1.1402 0.0766 0.047 Uiso 1 1 calc R . .
C1 C 0.6145(3) 1.0238(4) -0.2016(3) 0.0454(10) Uani 1 1 d . . .
H1 H 0.6579 1.0600 -0.2303 0.054 Uiso 1 1 calc R . .
C5 C 0.5890(3) 0.9454(4) -0.0590(3) 0.0457(11) Uani 1 1 d . . .
H5 H 0.6141 0.9297 0.0096 0.055 Uiso 1 1 calc R . .
C21 C 1.3441(3) 1.0076(4) 0.4322(3) 0.0450(10) Uani 1 1 d . . .
H21 H 1.4072 1.0514 0.4581 0.054 Uiso 1 1 calc R . .
C3 C 0.4488(3) 0.9336(4) -0.2221(4) 0.0569(13) Uani 1 1 d . . .
H3 H 0.3798 0.9115 -0.2632 0.068 Uiso 1 1 calc R . .
C10 C 0.8585(3) 0.8753(4) 0.2456(3) 0.0458(11) Uani 1 1 d . . .
H10 H 0.8582 0.8275 0.1925 0.055 Uiso 1 1 calc R . .
C4 C 0.4871(3) 0.9093(4) -0.1204(3) 0.0548(12) Uani 1 1 d . . .
H4 H 0.4446 0.8686 -0.0931 0.066 Uiso 1 1 calc R . .
C15 C 1.1324(3) 1.1609(4) 0.2207(3) 0.0438(10) Uani 1 1 d . . .
H15A H 1.0909 1.2345 0.2064 0.053 Uiso 1 1 calc R . .
H15B H 1.1434 1.1361 0.1607 0.053 Uiso 1 1 calc R . .
C11 C 0.8020(4) 0.8377(5) 0.3016(4) 0.0673(15) Uani 1 1 d . . .
H11 H 0.7640 0.7660 0.2862 0.081 Uiso 1 1 calc R . .
C12 C 0.8023(4) 0.9070(7) 0.3807(5) 0.085(2) Uani 1 1 d . . .
H12 H 0.7654 0.8815 0.4198 0.102 Uiso 1 1 calc R . .
C2 C 0.5123(4) 0.9900(4) -0.2620(3) 0.0563(12) Uani 1 1 d . . .
H2 H 0.4866 1.0060 -0.3306 0.068 Uiso 1 1 calc R . .
C14 C 0.9127(3) 1.0526(4) 0.3436(3) 0.0515(12) Uani 1 1 d . . .
C13 C 0.8569(4) 1.0141(7) 0.4020(3) 0.0754(17) Uani 1 1 d . . .
H13 H 0.8567 1.0610 0.4555 0.090 Uiso 1 1 calc R . .
N2 N 1.0024(3) 0.8456(4) 0.0865(3) 0.0497(9) Uani 1 1 d . . .
C26 C 1.2387(3) 1.1776(4) 0.3094(3) 0.0505(11) Uani 1 1 d . . .
H26A H 1.2958 1.1956 0.2867 0.061 Uiso 1 1 calc R . .
H26B H 1.2344 1.2412 0.3538 0.061 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
Br1 0.0856(4) 0.0798(4) 0.0473(3) -0.0255(3) 0.0038(3) 0.0268(3)
N3 0.0295(17) 0.0324(18) 0.0310(17) -0.0005(14) -0.0001(14) -0.0017(15)
C22 0.034(2) 0.038(2) 0.036(2) -0.0076(19) 0.0038(19) -0.0028(19)
C18 0.021(2) 0.067(3) 0.026(2) -0.014(2) 0.0023(17) 0.001(2)
C17 0.032(2) 0.031(2) 0.027(2) -0.0053(17) 0.0058(17) 0.0013(18)
C19 0.042(3) 0.039(2) 0.040(2) -0.0018(19) 0.008(2) 0.005(2)
C6 0.033(2) 0.031(2) 0.032(2) -0.0039(17) 0.0039(18) 0.0076(18)
C24 0.027(2) 0.035(2) 0.0252(19) -0.0062(17) 0.0031(16) -0.0019(17)
C8 0.033(2) 0.047(3) 0.031(2) 0.0034(18) 0.0045(18) 0.0052(19)
C20 0.034(2) 0.054(3) 0.038(2) 0.002(2) -0.0010(19) 0.011(2)
C7 0.034(2) 0.035(2) 0.032(2) 0.0033(17) 0.0081(18) 0.0057(18)
C25 0.026(2) 0.041(3) 0.033(2) 0.000(2) 0.0070(17) -0.0068(18)
C9 0.029(2) 0.052(3) 0.028(2) 0.0056(19) 0.0035(17) 0.011(2)
C23 0.037(2) 0.043(2) 0.029(2) 0.0036(18) 0.0038(18) 0.0062(19)
C1 0.051(3) 0.041(2) 0.033(2) -0.0028(19) 0.004(2) -0.001(2)
C5 0.037(2) 0.062(3) 0.033(2) -0.001(2) 0.007(2) 0.002(2)
C21 0.032(2) 0.046(3) 0.044(2) -0.006(2) 0.001(2) -0.001(2)
C3 0.037(3) 0.053(3) 0.055(3) -0.013(2) -0.010(2) 0.002(2)
C10 0.028(2) 0.065(3) 0.043(2) 0.015(2) 0.0117(19) 0.005(2)
C4 0.037(3) 0.063(3) 0.059(3) -0.008(2) 0.011(2) -0.004(2)
C15 0.039(2) 0.036(2) 0.045(2) 0.0000(19) 0.0043(19) -0.003(2)
C11 0.037(3) 0.099(4) 0.066(3) 0.037(3) 0.020(2) 0.017(3)
C12 0.051(3) 0.143(6) 0.071(4) 0.053(4) 0.036(3) 0.036(4)
C2 0.067(3) 0.048(3) 0.032(2) -0.002(2) -0.005(2) -0.003(2)
C14 0.047(3) 0.072(3) 0.028(2) -0.001(2) 0.005(2) 0.025(2)
C13 0.057(3) 0.131(6) 0.037(3) 0.013(3) 0.017(3) 0.043(4)
N2 0.047(2) 0.056(2) 0.044(2) -0.0147(19) 0.0154(17) -0.0024(18)
C26 0.039(2) 0.039(3) 0.053(3) 0.002(2) -0.005(2) -0.0034(19)

_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
Br1 C14 1.901(5) . ?
N3 C17 1.407(5) . ?
N3 C24 1.447(4) . ?
N3 C15 1.466(5) . ?
C22 C21 1.369(5) . ?
C22 C17 1.392(5) . ?
C22 C26 1.505(6) . ?
C18 C19 1.373(5) . ?
C18 C17 1.414(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.384(6) . ?
C19 H19 0.9300 . ?
C6 C5 1.379(5) . ?
C6 C1 1.392(5) . ?
C6 C7 1.466(5) . ?
C24 C25 1.503(6) . ?
C24 C9 1.533(5) . ?
C24 C23 1.557(5) . ?
C8 C7 1.320(5) . ?
C8 C23 1.495(5) . ?
C8 H8 0.9300 . ?
C20 C21 1.385(6) . ?
C20 H20 0.9300 . ?
C7 H7 0.9300 . ?
C25 N2 1.146(5) . ?
C9 C14 1.387(5) . ?
C9 C10 1.397(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C1 C2 1.378(6) . ?
C1 H1 0.9300 . ?
C5 C4 1.386(6) . ?
C5 H5 0.9300 . ?
C21 H21 0.9300 . ?
C3 C2 1.357(6) . ?
C3 C4 1.381(6) . ?
C3 H3 0.9300 . ?
C10 C11 1.373(6) . ?
C10 H10 0.9300 . ?
C4 H4 0.9300 . ?
C15 C26 1.530(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C11 C12 1.374(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(8) . ?
C12 H12 0.9300 . ?
C2 H2 0.9300 . ?
C14 C13 1.397(7) . ?
C13 H13 0.9300 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?

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
C17 N3 C24 122.6(3) . . ?
C17 N3 C15 108.4(3) . . ?
C24 N3 C15 123.3(3) . . ?
C21 C22 C17 120.4(4) . . ?
C21 C22 C26 130.5(4) . . ?
C17 C22 C26 109.2(3) . . ?
C19 C18 C17 116.6(4) . . ?
C19 C18 H18 121.7 . . ?
C17 C18 H18 121.7 . . ?
C22 C17 N3 109.0(3) . . ?
C22 C17 C18 121.0(3) . . ?
N3 C17 C18 129.9(3) . . ?
C18 C19 C20 122.6(4) . . ?
C18 C19 H19 118.7 . . ?
C20 C19 H19 118.7 . . ?
C5 C6 C1 118.0(3) . . ?
C5 C6 C7 122.6(3) . . ?
C1 C6 C7 119.4(4) . . ?
N3 C24 C25 107.6(3) . . ?
N3 C24 C9 111.1(3) . . ?
C25 C24 C9 111.0(3) . . ?
N3 C24 C23 111.3(3) . . ?
C25 C24 C23 106.2(3) . . ?
C9 C24 C23 109.5(3) . . ?
C7 C8 C23 124.6(4) . . ?
C7 C8 H8 117.7 . . ?
C23 C8 H8 117.7 . . ?
C19 C20 C21 119.9(4) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.0 . . ?
C8 C7 C6 126.8(4) . . ?
C8 C7 H7 116.6 . . ?
C6 C7 H7 116.6 . . ?
N2 C25 C24 173.2(4) . . ?
C14 C9 C10 116.9(4) . . ?
C14 C9 C24 123.1(4) . . ?
C10 C9 C24 119.9(3) . . ?
C8 C23 C24 112.2(3) . . ?
C8 C23 H23A 109.2 . . ?
C24 C23 H23A 109.2 . . ?
C8 C23 H23B 109.2 . . ?
C24 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C2 C1 C6 120.9(4) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C6 C5 C4 120.8(4) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C22 C21 C20 119.4(4) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C2 C3 C4 119.8(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C11 C10 C9 122.6(5) . . ?
C11 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
C3 C4 C5 120.0(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N3 C15 C26 103.1(3) . . ?
N3 C15 H15A 111.1 . . ?
C26 C15 H15A 111.1 . . ?
N3 C15 H15B 111.1 . . ?
C26 C15 H15B 111.1 . . ?
H15A C15 H15B 109.1 . . ?
C10 C11 C12 119.3(5) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C13 120.2(5) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C9 C14 C13 120.9(5) . . ?
C9 C14 Br1 123.9(3) . . ?
C13 C14 Br1 115.2(4) . . ?
C12 C13 C14 120.0(5) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C22 C26 C15 102.5(3) . . ?
C22 C26 H26A 111.3 . . ?
C15 C26 H26A 111.3 . . ?
C22 C26 H26B 111.3 . . ?
C15 C26 H26B 111.3 . . ?
H26A C26 H26B 109.2 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.92
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.957
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.052