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

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Ken Kamikawa'
_publ_contact_author_email       KAMIKAWA@C.S.OSAKAFU-U.AC.JP

_publ_section_title              
;
Induction of one-handed helical oligo(p-benzamide)s by
domino effect based on planar-axial-helical chirality relay
;
loop_
_publ_author_name
'Ken Kamikawa'
'Keisuke Fukumoto'
'Masaru Furusyo'
'Hiroyuki Matsuzaka'
'Shin Takemoto'
;
M.Uemura
;
'Kohei Yoshihara'

# Attachment 'kamikawa-shelxl1.cif'

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 705176'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 Fe I N O'
_chemical_formula_weight         445.07

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   P41212

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+1/2, x+1/2, z+1/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'y, x, -z'
'x+1/2, -y+1/2, -z+3/4'
'-y, -x, -z+1/2'

_cell_length_a                   11.742(3)
_cell_length_b                   11.742(3)
_cell_length_c                   24.521(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3381.0(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1744
_exptl_absorpt_coefficient_mu    2.719
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7727
_exptl_absorpt_correction_T_max  0.7727
_exptl_absorpt_process_details   abscor

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'rigaku raxis rapid'
_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            32883
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3878
_reflns_number_gt                3513
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'rigaku process auto'
_computing_cell_refinement       'rigaku process auto'
_computing_data_reduction        'rigaku process auto'
_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^)+(0.0483P)^2^+1.2132P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_number_reflns         3878
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0827
_refine_ls_wR_factor_gt          0.0801
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
I1 I 0.57739(3) 0.31419(2) 0.013027(12) 0.07655(11) Uani 1 1 d . . .
Fe1 Fe 0.60373(4) 0.14950(5) 0.13999(2) 0.05877(14) Uani 1 1 d . . .
O1 O 0.4790(3) 0.0270(3) 0.02479(14) 0.0875(10) Uani 1 1 d . . .
N1 N 0.2995(3) 0.0579(3) 0.05427(13) 0.0561(6) Uani 1 1 d . . .
C1 C 0.5244(3) 0.2547(3) 0.08872(14) 0.0536(7) Uani 1 1 d . . .
C2 C 0.5440(3) 0.3122(4) 0.13879(18) 0.0659(9) Uani 1 1 d . . .
H2 H 0.5857 0.3787 0.1438 0.079 Uiso 1 1 calc R . .
C3 C 0.4876(4) 0.2482(5) 0.17968(16) 0.0730(11) Uani 1 1 d . . .
H3 H 0.4863 0.2660 0.2166 0.088 Uiso 1 1 calc R . .
C4 C 0.4337(3) 0.1537(4) 0.15567(16) 0.0646(9) Uani 1 1 d . . .
H4 H 0.3915 0.0985 0.1739 0.078 Uiso 1 1 calc R . .
C5 C 0.4553(3) 0.1577(3) 0.09827(14) 0.0517(7) Uani 1 1 d . . .
C6 C 0.4142(3) 0.0756(3) 0.05605(14) 0.0566(8) Uani 1 1 d . . .
C7 C 0.2559(4) -0.0312(4) 0.01783(18) 0.0741(11) Uani 1 1 d . . .
H7A H 0.2497 -0.0015 -0.0185 0.111 Uiso 1 1 calc R . .
H7B H 0.1822 -0.0553 0.0302 0.111 Uiso 1 1 calc R . .
H7C H 0.3071 -0.0948 0.0180 0.111 Uiso 1 1 calc R . .
C8 C 0.2195(3) 0.1259(3) 0.08239(14) 0.0514(7) Uani 1 1 d . . .
C9 C 0.1364(3) 0.0756(4) 0.11429(17) 0.0663(10) Uani 1 1 d . . .
H9 H 0.1334 -0.0034 0.1170 0.080 Uiso 1 1 calc R . .
C10 C 0.0582(3) 0.1408(5) 0.14202(18) 0.0763(12) Uani 1 1 d . . .
H10 H 0.0026 0.1059 0.1633 0.092 Uiso 1 1 calc R . .
C11 C 0.0621(4) 0.2570(5) 0.1384(2) 0.0855(14) Uani 1 1 d . . .
H11 H 0.0097 0.3013 0.1573 0.103 Uiso 1 1 calc R . .
C12 C 0.1437(4) 0.3076(4) 0.1066(2) 0.0786(12) Uani 1 1 d . . .
H12 H 0.1465 0.3866 0.1045 0.094 Uiso 1 1 calc R . .
C13 C 0.2214(3) 0.2440(3) 0.07788(17) 0.0620(9) Uani 1 1 d . . .
H13 H 0.2748 0.2795 0.0556 0.074 Uiso 1 1 calc R . .
C14 C 0.7018(5) 0.0689(7) 0.1959(3) 0.114(2) Uani 1 1 d . . .
H14 H 0.6882 0.0664 0.2333 0.137 Uiso 1 1 calc R . .
C15 C 0.7647(4) 0.1514(7) 0.1685(4) 0.115(2) Uani 1 1 d . . .
H15 H 0.8011 0.2140 0.1839 0.138 Uiso 1 1 calc R . .
C16 C 0.7623(4) 0.1213(7) 0.1126(3) 0.117(3) Uani 1 1 d . . .
H16 H 0.7975 0.1608 0.0844 0.140 Uiso 1 1 calc R . .
C17 C 0.6973(5) 0.0210(7) 0.1072(3) 0.110(2) Uani 1 1 d . . .
H17 H 0.6811 -0.0173 0.0750 0.131 Uiso 1 1 calc R . .
C18 C 0.6632(5) -0.0087(6) 0.1578(4) 0.111(2) Uani 1 1 d . . .
H18 H 0.6196 -0.0726 0.1660 0.133 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
I1 0.0911(2) 0.06324(16) 0.07533(16) 0.01212(13) 0.00319(14) -0.01079(14)
Fe1 0.0373(2) 0.0704(3) 0.0686(3) 0.0109(2) -0.0006(2) 0.0016(2)
O1 0.0672(18) 0.094(2) 0.101(2) -0.0363(19) 0.0250(17) -0.0096(16)
N1 0.0526(15) 0.0490(15) 0.0666(16) -0.0048(13) -0.0028(13) -0.0051(12)
C1 0.0469(17) 0.0497(17) 0.0643(18) -0.0018(15) -0.0013(14) -0.0005(14)
C2 0.0562(19) 0.064(2) 0.078(2) -0.0134(19) -0.0067(18) -0.0029(17)
C3 0.051(2) 0.105(3) 0.063(2) -0.020(2) -0.0020(17) 0.000(2)
C4 0.0391(16) 0.088(3) 0.0665(19) -0.0018(18) 0.0062(15) -0.0004(17)
C5 0.0372(14) 0.0583(19) 0.0597(17) -0.0007(15) 0.0042(13) 0.0036(13)
C6 0.0564(19) 0.0530(17) 0.0604(18) -0.0039(15) 0.0055(15) -0.0067(16)
C7 0.085(3) 0.062(2) 0.075(2) -0.010(2) -0.006(2) -0.019(2)
C8 0.0422(15) 0.0588(19) 0.0534(16) 0.0003(14) -0.0085(13) -0.0017(13)
C9 0.0449(16) 0.078(2) 0.076(2) 0.012(2) -0.0099(16) -0.0040(17)
C10 0.0409(17) 0.115(4) 0.073(2) 0.014(2) -0.0034(17) 0.007(2)
C11 0.054(2) 0.110(4) 0.092(3) -0.015(3) -0.008(2) 0.024(2)
C12 0.061(2) 0.071(2) 0.104(3) -0.020(3) -0.018(2) 0.013(2)
C13 0.0500(19) 0.058(2) 0.078(2) -0.0014(19) -0.0128(17) 0.0013(15)
C14 0.073(3) 0.164(7) 0.105(4) 0.050(4) -0.014(3) 0.032(4)
C15 0.044(2) 0.144(6) 0.158(6) 0.002(5) -0.027(3) 0.008(3)
C16 0.048(2) 0.155(6) 0.148(6) 0.070(5) 0.032(3) 0.032(3)
C17 0.079(4) 0.120(5) 0.129(5) -0.005(4) 0.000(4) 0.046(4)
C18 0.083(4) 0.095(4) 0.155(6) 0.036(4) -0.019(4) 0.028(3)

_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
I1 C1 2.078(3) . ?
Fe1 C1 1.994(4) . ?
Fe1 C15 2.016(5) . ?
Fe1 C5 2.023(3) . ?
Fe1 C16 2.007(5) . ?
Fe1 C2 2.035(4) . ?
Fe1 C4 2.034(3) . ?
Fe1 C3 2.038(4) . ?
Fe1 C14 2.026(5) . ?
Fe1 C18 2.032(6) . ?
Fe1 C17 2.032(6) . ?
O1 C6 1.221(5) . ?
N1 C6 1.364(5) . ?
N1 C8 1.413(5) . ?
N1 C7 1.468(5) . ?
C1 C5 1.418(5) . ?
C1 C2 1.420(5) . ?
C2 C3 1.417(6) . ?
C3 C4 1.406(6) . ?
C4 C5 1.431(5) . ?
C5 C6 1.494(5) . ?
C8 C9 1.384(5) . ?
C8 C13 1.391(5) . ?
C9 C10 1.376(6) . ?
C10 C11 1.368(8) . ?
C11 C12 1.370(8) . ?
C12 C13 1.374(6) . ?
C14 C15 1.392(10) . ?
C14 C18 1.381(10) . ?
C15 C16 1.416(10) . ?
C16 C17 1.410(11) . ?
C17 C18 1.351(10) . ?

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 Fe1 C15 130.6(3) . . ?
C1 Fe1 C5 41.33(14) . . ?
C15 Fe1 C5 169.4(3) . . ?
C1 Fe1 C16 109.0(2) . . ?
C15 Fe1 C16 41.2(3) . . ?
C5 Fe1 C16 129.7(3) . . ?
C1 Fe1 C2 41.25(15) . . ?
C15 Fe1 C2 108.5(3) . . ?
C5 Fe1 C2 69.58(14) . . ?
C16 Fe1 C2 118.0(3) . . ?
C1 Fe1 C4 69.22(16) . . ?
C15 Fe1 C4 148.7(3) . . ?
C5 Fe1 C4 41.30(14) . . ?
C16 Fe1 C4 168.0(3) . . ?
C2 Fe1 C4 68.99(17) . . ?
C1 Fe1 C3 68.64(16) . . ?
C15 Fe1 C3 117.1(3) . . ?
C5 Fe1 C3 68.76(14) . . ?
C16 Fe1 C3 151.0(3) . . ?
C2 Fe1 C3 40.73(19) . . ?
C4 Fe1 C3 40.41(17) . . ?
C1 Fe1 C14 169.2(3) . . ?
C15 Fe1 C14 40.3(3) . . ?
C5 Fe1 C14 148.7(3) . . ?
C16 Fe1 C14 67.8(3) . . ?
C2 Fe1 C14 130.1(3) . . ?
C4 Fe1 C14 116.2(2) . . ?
C3 Fe1 C14 108.8(3) . . ?
C1 Fe1 C18 149.6(3) . . ?
C15 Fe1 C18 67.3(3) . . ?
C5 Fe1 C18 116.6(2) . . ?
C16 Fe1 C18 66.6(3) . . ?
C2 Fe1 C18 168.4(3) . . ?
C4 Fe1 C18 108.6(2) . . ?
C3 Fe1 C18 130.3(3) . . ?
C14 Fe1 C18 39.8(3) . . ?
C1 Fe1 C17 117.6(2) . . ?
C15 Fe1 C17 68.8(3) . . ?
C5 Fe1 C17 107.5(2) . . ?
C16 Fe1 C17 40.8(3) . . ?
C2 Fe1 C17 151.3(3) . . ?
C4 Fe1 C17 128.6(3) . . ?
C3 Fe1 C17 166.7(3) . . ?
C14 Fe1 C17 67.3(3) . . ?
C18 Fe1 C17 38.8(3) . . ?
C6 N1 C8 123.7(3) . . ?
C6 N1 C7 118.2(3) . . ?
C8 N1 C7 117.9(3) . . ?
C5 C1 C2 109.4(3) . . ?
C5 C1 Fe1 70.4(2) . . ?
C2 C1 Fe1 70.9(2) . . ?
C5 C1 I1 126.1(3) . . ?
C2 C1 I1 124.3(3) . . ?
Fe1 C1 I1 129.13(18) . . ?
C1 C2 C3 106.5(3) . . ?
C1 C2 Fe1 67.8(2) . . ?
C3 C2 Fe1 69.7(3) . . ?
C4 C3 C2 109.4(3) . . ?
C4 C3 Fe1 69.7(2) . . ?
C2 C3 Fe1 69.5(2) . . ?
C3 C4 C5 107.8(4) . . ?
C3 C4 Fe1 69.9(2) . . ?
C5 C4 Fe1 68.93(19) . . ?
C1 C5 C4 106.9(3) . . ?
C1 C5 C6 126.0(3) . . ?
C4 C5 C6 127.1(3) . . ?
C1 C5 Fe1 68.2(2) . . ?
C4 C5 Fe1 69.8(2) . . ?
C6 C5 Fe1 126.7(2) . . ?
O1 C6 N1 121.6(3) . . ?
O1 C6 C5 122.4(3) . . ?
N1 C6 C5 116.1(3) . . ?
C9 C8 C13 118.8(4) . . ?
C9 C8 N1 120.2(4) . . ?
C13 C8 N1 120.9(3) . . ?
C10 C9 C8 120.8(4) . . ?
C11 C10 C9 120.0(5) . . ?
C10 C11 C12 119.5(5) . . ?
C13 C12 C11 121.4(5) . . ?
C12 C13 C8 119.4(4) . . ?
C15 C14 C18 107.9(7) . . ?
C15 C14 Fe1 69.5(3) . . ?
C18 C14 Fe1 70.4(3) . . ?
C14 C15 C16 106.4(7) . . ?
C14 C15 Fe1 70.2(3) . . ?
C16 C15 Fe1 69.1(3) . . ?
C17 C16 C15 108.1(6) . . ?
C17 C16 Fe1 70.5(3) . . ?
C15 C16 Fe1 69.7(3) . . ?
C18 C17 C16 106.9(7) . . ?
C18 C17 Fe1 70.6(4) . . ?
C16 C17 Fe1 68.6(4) . . ?
C17 C18 C14 110.7(7) . . ?
C17 C18 Fe1 70.6(4) . . ?
C14 C18 Fe1 69.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.868
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.070