Electronic Supplementary Material for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2006

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Jong-In Hong'
_publ_contact_author_address     
;
Department of Chemistry
Seoul National University
College of Natural Sciences
Seoul
151-747
SOUTH KOREA
;

_publ_contact_author_email       JIHONG@SNU.AC.KR

_publ_section_title              
;
Formation of a discrete helical assembly through
charged hydrogen bonds
;
loop_
_publ_author_name
'Jong-In Hong.'
'Hae-Jo Kim.'
'Myoung Soo Lah.'
'Kyoung Jae Lee.'
;
Ho-Yong Lii
;

# Attachment 'o3_128tg_new.cif'

data_o3_128tg
_database_code_depnum_ccdc_archive 'CCDC 262127'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C60 H96 N12 O18'
_chemical_formula_weight         1273.49

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           Trigonal
_symmetry_space_group_name_H-M   R-3c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   27.5164(19)
_cell_length_b                   27.5164(19)
_cell_length_c                   14.685(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     9629.2(17)
_cell_formula_units_Z            6
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4648
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4104
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9619
_exptl_absorpt_correction_T_max  0.9807
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        <2.0
_diffrn_reflns_number            18655
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         28.30
_reflns_number_total             2641
_reflns_number_gt                1276
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    ORTEP3
_computing_publication_material  WinGX

_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^)+(0.1258P)^2^+12.2688P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2641
_refine_ls_number_parameters     188
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1472
_refine_ls_R_factor_gt           0.0729
_refine_ls_wR_factor_ref         0.2573
_refine_ls_wR_factor_gt          0.2045
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.068
_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
O1 O 0.31807(10) 0.49228(10) 1.05255(18) 0.0698(8) Uani 1 1 d . . .
O2 O 0.24232(12) 0.46389(12) 0.9688(2) 0.0885(9) Uani 1 1 d . . .
C6 C 0.30287(15) 0.42861(14) 0.9300(3) 0.0647(9) Uani 1 1 d . . .
H6 H 0.2843(15) 0.4214(15) 0.863(3) 0.078 Uiso 1 1 d . . .
C7 C 0.2872(2) 0.37457(17) 0.9827(3) 0.0829(12) Uani 1 1 d . . .
H7A H 0.3127(19) 0.3895(19) 1.036(3) 0.099 Uiso 1 1 d . . .
H7B H 0.248(2) 0.3552(18) 1.012(3) 0.099 Uiso 1 1 d . . .
C8 C 0.3029(3) 0.33707(18) 0.9296(4) 0.1084(18) Uani 1 1 d . . .
C9 C 0.28683(15) 0.46483(13) 0.9876(2) 0.0607(9) Uani 1 1 d . . .
H8A H 0.2918(15) 0.3006(16) 0.969(3) 0.073 Uiso 1 1 d . . .
H8B H 0.2840(16) 0.3274(16) 0.868(3) 0.073 Uiso 1 1 d . . .
N1 N 0.32140(13) 0.79733(12) 0.0448(2) 0.0650(8) Uani 1 1 d . . .
H1N H 0.2859(17) 0.7761(17) 0.023(3) 0.073(11) Uiso 1 1 d . . .
N2 N 0.40845(13) 0.82290(11) 0.0758(2) 0.0643(8) Uani 1 1 d . . .
H2N H 0.4377(18) 0.8207(16) 0.075(3) 0.072(12) Uiso 1 1 d . . .
C1 C 0.29011(14) 0.67901(13) 0.0453(2) 0.0539(8) Uani 1 1 d . . .
H1 H 0.2601(14) 0.6850(14) 0.046(2) 0.065 Uiso 1 1 d . . .
C2 C 0.34606(13) 0.72247(12) 0.0451(2) 0.0526(8) Uani 1 1 d . . .
C3 C 0.35896(13) 0.78145(13) 0.0536(2) 0.0557(8) Uani 1 1 d . . .
C4 C 0.34741(17) 0.85800(15) 0.0607(3) 0.0701(10) Uani 1 1 d . . .
H4A H 0.3267(16) 0.8647(15) 0.112(3) 0.084 Uiso 1 1 d . . .
H4B H 0.3411(17) 0.8750(17) 0.017(3) 0.084 Uiso 1 1 d . . .
C5 C 0.40832(16) 0.87590(15) 0.0815(3) 0.0698(10) Uani 1 1 d . . .
H5A H 0.4379(17) 0.9041(17) 0.036(3) 0.084 Uiso 1 1 d . . .
H5B H 0.4200(17) 0.8921(17) 0.146(3) 0.084 Uiso 1 1 d . . .
O1S O 0.1504(4) 0.3556(4) 0.9077(6) 0.132(4) Uani 0.485(11) 1 d PD A 1
H1S H 0.1822 0.3729 0.9321 0.198 Uiso 0.485(11) 1 calc PR A 1
C1S C 0.1154(4) 0.3289(3) 0.9653(6) 0.158(3) Uani 0.485(11) 1 d PD A 1
H1S1 H 0.0864 0.3397 0.9651 0.237 Uiso 0.485(11) 1 calc PR A 1
H1S2 H 0.1333 0.3366 1.0253 0.237 Uiso 0.485(11) 1 calc PR A 1
H1S3 H 0.0982 0.2887 0.9519 0.237 Uiso 0.485(11) 1 calc PR A 1
O2S O 0.1314(4) 0.3831(4) 0.9638(8) 0.138(4) Uani 0.515(11) 1 d PD A 2
H2S H 0.1667 0.4022 0.9649 0.206 Uiso 0.515(11) 1 calc PR A 2
C2S C 0.1154(4) 0.3289(3) 0.9653(6) 0.158(3) Uani 0.52 1 d PD A 2
H2S1 H 0.0852 0.3096 1.0099 0.237 Uiso 0.515(11) 1 calc PR A 2
H2S2 H 0.1473 0.3243 0.9822 0.237 Uiso 0.515(11) 1 calc PR A 2
H2S3 H 0.1018 0.3127 0.9048 0.237 Uiso 0.515(11) 1 calc PR A 2

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
O1 0.0598(15) 0.0527(14) 0.0922(19) 0.0007(13) 0.0062(13) 0.0247(12)
O2 0.0742(18) 0.099(2) 0.105(2) -0.0208(17) -0.0075(15) 0.0531(17)
C6 0.075(2) 0.0442(18) 0.078(2) 0.0024(16) -0.0004(18) 0.0317(16)
C7 0.097(3) 0.048(2) 0.105(3) 0.015(2) 0.007(3) 0.037(2)
C8 0.161(5) 0.052(2) 0.120(4) 0.004(3) -0.011(4) 0.058(3)
C9 0.054(2) 0.0451(18) 0.073(2) 0.0044(16) 0.0083(17) 0.0174(15)
N1 0.0561(18) 0.0519(17) 0.088(2) -0.0011(15) 0.0021(15) 0.0279(15)
N2 0.0531(18) 0.0504(17) 0.087(2) -0.0041(14) 0.0047(15) 0.0242(15)
C1 0.0510(18) 0.0545(19) 0.0582(19) 0.0028(14) 0.0013(14) 0.0278(16)
C2 0.0535(18) 0.0500(18) 0.0529(17) -0.0005(13) -0.0005(14) 0.0248(15)
C3 0.055(2) 0.0528(19) 0.0608(19) 0.0015(14) 0.0059(14) 0.0279(17)
C4 0.072(2) 0.050(2) 0.089(3) 0.0001(18) 0.006(2) 0.0310(19)
C5 0.063(2) 0.0476(19) 0.096(3) -0.0020(18) 0.013(2) 0.0251(17)
O1S 0.107(6) 0.125(8) 0.125(7) -0.019(6) 0.012(5) 0.029(6)
C1S 0.161(7) 0.120(6) 0.187(8) -0.019(5) 0.004(6) 0.066(5)
O2S 0.133(7) 0.099(6) 0.183(9) -0.014(6) -0.007(7) 0.060(5)
C2S 0.161(7) 0.120(6) 0.187(8) -0.019(5) 0.004(6) 0.066(5)

_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
O1 C9 1.253(4) . ?
O2 C9 1.243(4) . ?
C6 C6 1.504(7) 12_556 ?
C6 C9 1.530(5) . ?
C6 C7 1.535(5) . ?
C7 C8 1.518(7) . ?
C8 C8 1.501(12) 12_556 ?
N1 C3 1.314(4) . ?
N1 C4 1.470(5) . ?
N2 C3 1.307(4) . ?
N2 C5 1.462(4) . ?
C1 C2 1.385(4) 2_665 ?
C1 C2 1.400(4) . ?
C2 C1 1.385(4) 3_565 ?
C2 C3 1.483(4) . ?
C4 C5 1.523(6) . ?
O1S C1S 1.215(9) . ?

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
C6 C6 C9 112.7(3) 12_556 . ?
C6 C6 C7 111.5(3) 12_556 . ?
C9 C6 C7 108.7(3) . . ?
C8 C7 C6 111.2(4) . . ?
C8 C8 C7 111.6(4) 12_556 . ?
O2 C9 O1 123.6(3) . . ?
O2 C9 C6 117.8(3) . . ?
O1 C9 C6 118.6(3) . . ?
C3 N1 C4 110.2(3) . . ?
C3 N2 C5 111.3(3) . . ?
C2 C1 C2 120.2(3) 2_665 . ?
C1 C2 C1 119.8(3) 3_565 . ?
C1 C2 C3 120.4(3) 3_565 . ?
C1 C2 C3 119.6(3) . . ?
N2 C3 N1 112.6(3) . . ?
N2 C3 C2 123.4(3) . . ?
N1 C3 C2 123.9(3) . . ?
N1 C4 C5 103.4(3) . . ?
N2 C5 C4 102.5(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O2 0.91(4) 1.77(4) 2.642(4) 161(4) 3_564
N2 H2N O1 0.84(4) 1.89(4) 2.714(4) 169(4) 2_664
O1S H1S O2 0.84 2.27 2.923(10) 134.8 .
O2S H2S O2 0.84 1.92 2.733(10) 162.8 .

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.052

