# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Jie Zhang.'
_publ_contact_author_email       ZHANGJIE@FJIRSM.AC.CN

_publ_section_title              
;
Self-resolution of a hydrated helix from an achiral
zwitterionic salt, spontaneous chiral symmetry breaking in
crystallization, and redox chromism behavior of crystals
;
loop_
_publ_author_name
'Jie Zhang.'
'Chao-Yang Tu.'
'Wei-Min Xuan.'
'Qing-Xia Yao.'
'Hui Zhang.'

# Attachment 'CIF-B815456B.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 700752'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_absolute_configuration ' unk '
_chemical_formula_moiety         'C26 H20 N2 O4 5(H2 O)'
_chemical_formula_sum            'C26 H30 N2 O9'
_chemical_formula_weight         514.53

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   P3(2)21
_symmetry_space_group_name_Hall  P_32_2"

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

_cell_length_a                   9.6710(4)
_cell_length_b                   9.6710(4)
_cell_length_c                   22.6740(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     1836.54(17)
_cell_formula_units_Z            3
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4655
_cell_measurement_theta_min      2.4303
_cell_measurement_theta_max      27.4835

_exptl_crystal_description       Prism
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.3500
_exptl_crystal_size_mid          0.3000
_exptl_crystal_size_min          0.1800
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             804
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8644
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(R.H. Blessing, 1995&1997)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13804
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0133
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         4.21
_diffrn_reflns_theta_max         27.47
_reflns_number_total             1629
_reflns_number_gt                1518
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear(Rigaku Corp.,2000)'
_computing_cell_refinement       'CrystalClear(Rigaku Corp.,2000)'
_computing_data_reduction        'CrystalClear(Rigaku Corp.,2000)'
_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^)+(0.0689P)^2^+0.2465P] 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         1629
_refine_ls_number_parameters     180
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1176
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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 0.7250(2) 1.0003(3) 0.31377(9) 0.0761(6) Uani 1 1 d . . .
O2 O 0.5991(3) 0.8114(3) 0.38017(8) 0.0754(6) Uani 1 1 d . . .
N1 N 0.1738(2) 0.4655(2) 0.11096(7) 0.0427(4) Uani 1 1 d . . .
C1 C 0.6102(3) 0.8723(3) 0.33100(10) 0.0512(5) Uani 1 1 d . . .
C2 C 0.4750(3) 0.7854(3) 0.28749(9) 0.0462(5) Uani 1 1 d . . .
C3 C 0.4303(3) 0.8670(3) 0.24923(10) 0.0540(6) Uani 1 1 d . . .
H1 H 0.4822 0.9802 0.2509 0.065 Uiso 1 1 calc R . .
C4 C 0.3962(3) 0.6198(3) 0.28491(10) 0.0525(6) Uani 1 1 d . . .
H2 H 0.4231 0.5624 0.3122 0.063 Uiso 1 1 calc R . .
C5 C 0.3099(3) 0.7845(3) 0.20827(11) 0.0551(6) Uani 1 1 d . . .
H3 H 0.2780 0.8415 0.1828 0.066 Uiso 1 1 calc R . .
C6 C 0.2793(3) 0.5377(3) 0.24325(10) 0.0500(5) Uani 1 1 d . . .
H4 H 0.2283 0.4246 0.2413 0.060 Uiso 1 1 calc R . .
C7 C 0.2360(3) 0.6198(3) 0.20427(9) 0.0454(5) Uani 1 1 d . . .
C8 C 0.1119(3) 0.5300(3) 0.15774(10) 0.0516(6) Uani 1 1 d . . .
H6 H 0.0164 0.4407 0.1764 0.062 Uiso 1 1 calc R . .
H5 H 0.0793 0.6023 0.1394 0.062 Uiso 1 1 calc R . .
C9 C 0.3181(3) 0.5603(3) 0.08702(10) 0.0494(5) Uani 1 1 d . . .
H7 H 0.3802 0.6674 0.1002 0.059 Uiso 1 1 calc R . .
C10 C 0.0850(3) 0.3149(3) 0.09263(10) 0.0560(6) Uani 1 1 d . . .
H8 H -0.0162 0.2484 0.1103 0.067 Uiso 1 1 calc R . .
C11 C 0.3771(3) 0.5047(3) 0.04373(10) 0.0470(5) Uani 1 1 d . . .
H9 H 0.4800 0.5729 0.0276 0.056 Uiso 1 1 calc R . .
C12 C 0.1370(3) 0.2542(3) 0.04876(10) 0.0561(6) Uani 1 1 d . . .
H10 H 0.0708 0.1475 0.0357 0.067 Uiso 1 1 calc R . .
C13 C 0.2864(3) 0.3486(3) 0.02345(8) 0.0400(4) Uani 1 1 d . . .
O1W O 1.1490(4) 1.2829(4) 0.46263(11) 0.0972(9) Uani 1 1 d . . .
O2W O 0.8507(4) 0.9748(4) 0.45808(13) 0.1012(10) Uani 1 1 d . . .
O3W O 1.0000 1.2663(4) 0.3333 0.1118(16) Uani 1 2 d SD . .
H1W H 1.194(6) 1.285(5) 0.4296(19) 0.099(13) Uiso 1 1 d . . .
H2W H 0.777(6) 0.921(6) 0.4364(18) 0.103(15) Uiso 1 1 d . . .
H3W H 0.930(9) 1.175(5) 0.318(3) 0.22(4) Uiso 1 1 d 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
O1 0.0564(11) 0.0692(13) 0.0690(11) -0.0049(9) -0.0016(9) 0.0061(10)
O2 0.0764(14) 0.0766(14) 0.0581(10) -0.0005(10) -0.0179(10) 0.0270(11)
N1 0.0390(9) 0.0498(10) 0.0377(8) -0.0027(7) -0.0019(7) 0.0210(8)
C1 0.0487(12) 0.0538(13) 0.0516(12) -0.0093(10) 0.0002(10) 0.0261(11)
C2 0.0469(12) 0.0469(12) 0.0431(10) -0.0041(9) 0.0036(9) 0.0221(10)
C3 0.0590(14) 0.0399(11) 0.0598(12) -0.0007(9) -0.0027(11) 0.0222(10)
C4 0.0678(16) 0.0457(12) 0.0451(10) -0.0009(9) -0.0038(10) 0.0292(11)
C5 0.0623(15) 0.0493(13) 0.0564(12) 0.0010(10) -0.0051(11) 0.0299(12)
C6 0.0580(14) 0.0403(11) 0.0458(10) -0.0026(9) 0.0013(9) 0.0201(11)
C7 0.0425(11) 0.0529(12) 0.0402(9) -0.0046(9) 0.0046(8) 0.0235(10)
C8 0.0411(11) 0.0638(15) 0.0491(11) -0.0121(11) 0.0007(9) 0.0257(10)
C9 0.0433(12) 0.0442(12) 0.0533(11) -0.0029(9) 0.0054(9) 0.0162(10)
C10 0.0407(12) 0.0548(14) 0.0566(12) -0.0052(11) 0.0088(10) 0.0119(11)
C11 0.0414(11) 0.0442(12) 0.0508(11) -0.0006(9) 0.0057(9) 0.0180(10)
C12 0.0485(13) 0.0470(12) 0.0552(12) -0.0096(10) 0.0059(10) 0.0105(11)
C13 0.0396(10) 0.0445(11) 0.0341(8) 0.0021(8) -0.0015(7) 0.0196(9)
O1W 0.1031(19) 0.142(3) 0.0633(12) 0.0098(14) 0.0155(13) 0.0741(19)
O2W 0.0865(17) 0.099(2) 0.1015(19) 0.0097(15) -0.0362(15) 0.0343(16)
O3W 0.059(2) 0.0625(15) 0.212(5) -0.0145(14) -0.029(3) 0.0297(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
O1 C1 1.242(3) . ?
O2 C1 1.240(3) . ?
N1 C10 1.334(3) . ?
N1 C9 1.342(3) . ?
N1 C8 1.500(3) . ?
C1 C2 1.513(3) . ?
C2 C3 1.379(3) . ?
C2 C4 1.389(3) . ?
C3 C5 1.388(4) . ?
C3 H1 0.9500 . ?
C4 C6 1.380(3) . ?
C4 H2 0.9500 . ?
C5 C7 1.385(3) . ?
C5 H3 0.9500 . ?
C6 C7 1.385(3) . ?
C6 H4 0.9500 . ?
C7 C8 1.505(3) . ?
C8 H6 0.9900 . ?
C8 H5 0.9900 . ?
C9 C11 1.373(3) . ?
C9 H7 0.9500 . ?
C10 C12 1.372(3) . ?
C10 H8 0.9500 . ?
C11 C13 1.391(3) . ?
C11 H9 0.9500 . ?
C12 C13 1.390(3) . ?
C12 H10 0.9500 . ?
C13 C13 1.489(4) 6 ?
O1W H1W 0.86(4) . ?
O2W H2W 0.80(5) . ?
O3W H3W 0.88(2) . ?

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
C10 N1 C9 120.09(18) . . ?
C10 N1 C8 120.12(19) . . ?
C9 N1 C8 119.8(2) . . ?
O2 C1 O1 125.3(2) . . ?
O2 C1 C2 118.5(2) . . ?
O1 C1 C2 116.2(2) . . ?
C3 C2 C4 119.0(2) . . ?
C3 C2 C1 121.5(2) . . ?
C4 C2 C1 119.4(2) . . ?
C2 C3 C5 120.3(2) . . ?
C2 C3 H1 119.8 . . ?
C5 C3 H1 119.8 . . ?
C6 C4 C2 120.8(2) . . ?
C6 C4 H2 119.6 . . ?
C2 C4 H2 119.6 . . ?
C7 C5 C3 120.5(2) . . ?
C7 C5 H3 119.8 . . ?
C3 C5 H3 119.8 . . ?
C4 C6 C7 120.2(2) . . ?
C4 C6 H4 119.9 . . ?
C7 C6 H4 119.9 . . ?
C5 C7 C6 119.2(2) . . ?
C5 C7 C8 120.9(2) . . ?
C6 C7 C8 119.9(2) . . ?
N1 C8 C7 111.49(18) . . ?
N1 C8 H6 109.3 . . ?
C7 C8 H6 109.3 . . ?
N1 C8 H5 109.3 . . ?
C7 C8 H5 109.3 . . ?
H6 C8 H5 108.0 . . ?
N1 C9 C11 121.0(2) . . ?
N1 C9 H7 119.5 . . ?
C11 C9 H7 119.5 . . ?
N1 C10 C12 121.3(2) . . ?
N1 C10 H8 119.4 . . ?
C12 C10 H8 119.4 . . ?
C9 C11 C13 120.05(19) . . ?
C9 C11 H9 120.0 . . ?
C13 C11 H9 120.0 . . ?
C10 C12 C13 120.1(2) . . ?
C10 C12 H10 120.0 . . ?
C13 C12 H10 120.0 . . ?
C12 C13 C11 117.46(19) . . ?
C12 C13 C13 121.78(13) . 6 ?
C11 C13 C13 120.76(12) . 6 ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.033