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

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Yong Cui'
_publ_contact_author_email       YONGCUI@SJTU.EDU.CN

_publ_section_title              
;
Water Clusters Induced Assembly
of Chiral Organic Microstructures Showing Reversible
Phase Transformations and Luminescence Switching
;
loop_
_publ_author_name
'Yong Cui.'
'Yu Fang.'
'Yan Liu.'
'Guozan Yuan.'
'Chengfeng Zhu.'

# Attachment 'CIF.cif'

data_(R)-1.2H2O
_database_code_depnum_ccdc_archive 'CCDC 747373'
#TrackingRef 'CIF.cif'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H32 N2 O4'
_chemical_formula_weight         460.56

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2

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

_cell_length_a                   12.366(5)
_cell_length_b                   27.132(10)
_cell_length_c                   7.849(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2633.2(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    4625
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25

_exptl_crystal_description       Tubule
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(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  ?
_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            10876
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0659
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4625
_reflns_number_gt                2730
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 1990)'
_computing_publication_material  SHELXL-97

_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^)+(0.1173P)^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    mixed
_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   2(5)
_refine_ls_number_reflns         4625
_refine_ls_number_parameters     271
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0674
_refine_ls_wR_factor_ref         0.1927
_refine_ls_wR_factor_gt          0.1739
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_restrained_S_all      1.871
_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 0.5761(5) 0.3991(2) 0.1131(6) 0.093(3) Uani 1 1 d G . .
C1 C 0.6838(5) 0.3849(2) 0.1003(6) 0.087(3) Uani 1 1 d G . .
H1A H 0.7183 0.3854 -0.0050 0.104 Uiso 1 1 calc R . .
C2 C 0.7400(3) 0.3700(2) 0.2448(7) 0.077(3) Uani 1 1 d G . .
H2A H 0.8120 0.3605 0.2363 0.093 Uiso 1 1 calc R . .
C3 C 0.6884(4) 0.3694(2) 0.4022(6) 0.058(2) Uani 1 1 d G . .
C4 C 0.5807(4) 0.3836(2) 0.4151(6) 0.072(2) Uani 1 1 d G . .
H4A H 0.5462 0.3831 0.5203 0.087 Uiso 1 1 calc R . .
C5 C 0.5246(3) 0.3985(2) 0.2705(8) 0.089(3) Uani 1 1 d G . .
H5A H 0.4525 0.4080 0.2791 0.107 Uiso 1 1 calc R . .
C12 C 0.6582(8) 0.2623(5) 0.9135(17) 0.112(4) Uani 1 1 d . . .
H12A H 0.7004 0.2479 1.0033 0.168 Uiso 1 1 calc R . .
H12B H 0.6279 0.2366 0.8442 0.168 Uiso 1 1 calc R . .
H12C H 0.6009 0.2817 0.9620 0.168 Uiso 1 1 calc R . .
C6 C 0.7434(3) 0.34913(18) 0.5635(6) 0.058(2) Uani 1 1 d G . .
C7 C 0.8527(3) 0.35597(17) 0.5975(6) 0.054(2) Uani 1 1 d GD . .
C8 C 0.9004(3) 0.33227(18) 0.7353(7) 0.054(2) Uani 1 1 d G . .
C9 C 0.8388(4) 0.30173(19) 0.8392(6) 0.063(2) Uani 1 1 d G . .
C10 C 0.7295(3) 0.29489(19) 0.8052(7) 0.066(2) Uani 1 1 d G . .
C11 C 0.6818(3) 0.31859(19) 0.6674(7) 0.060(2) Uani 1 1 d G . .
H11A H 0.6087 0.3140 0.6446 0.072 Uiso 1 1 calc R . .
C13 C 0.8907(8) 0.2735(4) 0.9803(16) 0.096(3) Uani 1 1 d . . .
H13A H 0.8370 0.2541 1.0379 0.144 Uiso 1 1 calc R . .
H13B H 0.9231 0.2961 1.0595 0.144 Uiso 1 1 calc R . .
H13C H 0.9453 0.2522 0.9344 0.144 Uiso 1 1 calc R . .
C14 C 0.8964(8) 0.4369(3) 0.5028(14) 0.086(3) Uani 1 1 d D . .
H14A H 0.9445 0.4544 0.4285 0.130 Uiso 1 1 calc R . .
H14B H 0.9069 0.4478 0.6179 0.130 Uiso 1 1 calc R . .
H14C H 0.8230 0.4430 0.4692 0.130 Uiso 1 1 calc R . .
C15 C 1.0176(2) 0.34101(16) 0.7719(6) 0.0532(19) Uani 1 1 d G . .
C16 C 1.0450(3) 0.37158(17) 0.9073(6) 0.056(2) Uani 1 1 d GD . .
C17 C 1.1530(3) 0.38149(16) 0.9421(5) 0.055(2) Uani 1 1 d G . .
C18 C 1.2337(3) 0.36082(19) 0.8416(6) 0.062(2) Uani 1 1 d G . .
H18A H 1.3060 0.3674 0.8649 0.074 Uiso 1 1 calc R . .
C19 C 1.2063(3) 0.33024(18) 0.7062(6) 0.067(2) Uani 1 1 d G . .
C20 C 1.0982(3) 0.32033(14) 0.6714(5) 0.063(2) Uani 1 1 d G . .
C21 C 1.0667(5) 0.2850(2) 0.5324(7) 0.086(3) Uani 1 1 d G . .
H21A H 1.1305 0.2736 0.4747 0.129 Uiso 1 1 calc R . .
H21B H 1.0201 0.3013 0.4525 0.129 Uiso 1 1 calc R . .
H21C H 1.0294 0.2573 0.5812 0.129 Uiso 1 1 calc R . .
C22 C 1.2963(7) 0.3087(4) 0.6004(16) 0.101(4) Uani 1 1 d . . .
H22A H 1.2662 0.2884 0.5122 0.152 Uiso 1 1 calc R . .
H22B H 1.3426 0.2892 0.6716 0.152 Uiso 1 1 calc R . .
H22C H 1.3375 0.3349 0.5498 0.152 Uiso 1 1 calc R . .
C23 C 0.9390(8) 0.4403(3) 0.9903(16) 0.097(3) Uani 1 1 d D . .
H23A H 0.8819 0.4498 1.0665 0.146 Uiso 1 1 calc R . .
H23B H 0.9166 0.4459 0.8748 0.146 Uiso 1 1 calc R . .
H23C H 1.0025 0.4594 1.0142 0.146 Uiso 1 1 calc R . .
C24 C 1.1854(4) 0.41259(19) 1.0964(6) 0.061(2) Uani 1 1 d G . .
C25 C 1.1477(4) 0.40121(19) 1.2585(8) 0.075(3) Uani 1 1 d G . .
H25A H 1.0987 0.3756 1.2734 0.090 Uiso 1 1 calc R . .
C26 C 1.1832(5) 0.4281(2) 1.3984(6) 0.089(3) Uani 1 1 d G . .
H26A H 1.1580 0.4205 1.5068 0.107 Uiso 1 1 calc R . .
N2 N 1.2565(5) 0.4665(2) 1.3761(7) 0.085(2) Uani 1 1 d G . .
C27 C 1.2942(4) 0.47785(17) 1.2140(9) 0.079(3) Uani 1 1 d G . .
H27A H 1.3432 0.5035 1.1991 0.095 Uiso 1 1 calc R . .
C28 C 1.2587(4) 0.4509(2) 1.0741(6) 0.071(2) Uani 1 1 d G . .
H28A H 1.2839 0.4585 0.9656 0.086 Uiso 1 1 calc R . .
O1 O 0.9182(4) 0.3855(2) 0.4922(8) 0.0670(15) Uani 1 1 d D . .
O2 O 0.9623(4) 0.38972(19) 1.0132(7) 0.0631(15) Uani 1 1 d D . .
O3 O 0.5030(6) 0.4270(3) 0.7824(9) 0.103(2) Uani 1 1 d D . .
O4 O 0.3438(7) 0.4987(4) 0.7003(10) 0.114(3) Uani 1 1 d D . .
H41W H 0.311(8) 0.488(4) 0.596(9) 0.12(4) Uiso 1 1 d D . .
H31W H 0.516(10) 0.429(4) 0.902(6) 0.14(5) Uiso 1 1 d D . .
H42W H 0.389(11) 0.527(4) 0.678(15) 0.19(7) Uiso 1 1 d D . .
H32W H 0.445(11) 0.450(5) 0.759(16) 0.257 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
N1 0.091(6) 0.111(7) 0.078(6) 0.004(5) -0.018(5) 0.001(5)
C1 0.086(7) 0.112(8) 0.061(6) -0.017(6) -0.007(6) 0.000(6)
C2 0.070(5) 0.099(7) 0.063(6) -0.013(5) 0.010(5) 0.007(5)
C3 0.052(4) 0.062(5) 0.060(5) -0.008(4) -0.001(4) 0.000(3)
C4 0.060(5) 0.095(6) 0.062(6) 0.005(5) -0.001(5) 0.011(4)
C5 0.069(6) 0.122(8) 0.076(7) 0.012(6) -0.008(6) 0.014(5)
C12 0.082(6) 0.115(9) 0.139(10) 0.047(8) -0.010(7) -0.046(6)
C6 0.050(4) 0.048(4) 0.076(6) -0.008(4) 0.000(4) -0.002(3)
C7 0.050(4) 0.044(4) 0.069(5) -0.007(4) 0.008(4) 0.003(3)
C8 0.044(4) 0.048(4) 0.069(6) 0.008(4) -0.002(4) 0.002(3)
C9 0.050(4) 0.061(5) 0.079(6) 0.014(4) -0.001(4) -0.004(4)
C10 0.053(5) 0.059(5) 0.085(7) 0.010(5) 0.001(5) -0.009(4)
C11 0.046(4) 0.064(5) 0.070(6) 0.004(4) 0.002(4) -0.009(4)
C13 0.084(6) 0.082(6) 0.122(9) 0.046(6) -0.024(7) -0.013(5)
C14 0.101(7) 0.060(6) 0.098(8) 0.015(5) 0.007(6) -0.017(5)
C15 0.044(4) 0.048(4) 0.067(5) 0.008(4) 0.000(4) 0.001(3)
C16 0.050(4) 0.055(4) 0.063(5) 0.007(4) 0.010(4) 0.000(3)
C17 0.051(4) 0.054(5) 0.060(5) 0.012(4) -0.006(4) -0.004(3)
C18 0.042(4) 0.072(5) 0.072(6) 0.010(5) 0.001(4) -0.003(4)
C19 0.050(5) 0.068(5) 0.084(7) 0.014(5) 0.013(4) 0.005(4)
C20 0.057(5) 0.052(5) 0.081(6) 0.005(4) 0.006(4) 0.012(4)
C21 0.081(6) 0.072(6) 0.105(8) -0.024(5) 0.003(6) 0.012(4)
C22 0.057(5) 0.126(9) 0.120(9) -0.023(8) 0.015(6) 0.020(5)
C23 0.103(7) 0.073(7) 0.116(9) 0.002(6) 0.025(7) 0.022(5)
C24 0.045(4) 0.066(5) 0.072(6) 0.017(4) -0.002(4) 0.004(4)
C25 0.079(6) 0.080(6) 0.067(6) 0.012(5) -0.001(5) -0.014(5)
C26 0.097(7) 0.099(8) 0.070(7) 0.008(6) -0.013(6) -0.004(6)
N2 0.077(5) 0.077(5) 0.101(7) -0.007(5) -0.022(5) 0.016(4)
C27 0.064(6) 0.067(6) 0.106(9) 0.002(6) -0.012(6) -0.005(4)
C28 0.061(5) 0.073(6) 0.081(7) 0.008(5) -0.006(5) -0.010(4)
O1 0.059(3) 0.068(4) 0.073(4) 0.018(3) 0.009(3) -0.008(2)
O2 0.050(3) 0.069(4) 0.071(4) -0.002(3) 0.012(3) 0.003(2)
O3 0.104(5) 0.141(6) 0.065(5) 0.009(4) -0.013(4) 0.007(5)
O4 0.111(6) 0.140(7) 0.092(6) 0.009(5) -0.033(5) -0.023(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
N1 C1 1.3900 . ?
N1 C5 1.3900 . ?
C1 C2 1.3900 . ?
C1 H1A 0.9300 . ?
C2 C3 1.3900 . ?
C2 H2A 0.9300 . ?
C3 C4 1.3900 . ?
C3 C6 1.538(5) . ?
C4 C5 1.3900 . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C12 C10 1.510(10) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C6 C7 1.3900 . ?
C6 C11 1.3900 . ?
C7 C8 1.3900 . ?
C7 O1 1.407(6) . ?
C8 C9 1.3900 . ?
C8 C15 1.496(4) . ?
C9 C10 1.3900 . ?
C9 C13 1.491(10) . ?
C10 C11 1.3900 . ?
C11 H11A 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O1 1.421(9) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.3900 . ?
C15 C20 1.3900 . ?
C16 C17 1.3900 . ?
C16 O2 1.407(6) . ?
C17 C18 1.3900 . ?
C17 C24 1.529(6) . ?
C18 C19 1.3900 . ?
C18 H18A 0.9300 . ?
C19 C20 1.3900 . ?
C19 C22 1.507(9) . ?
C20 C21 1.5045 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 O2 1.413(9) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.3900 . ?
C24 C28 1.3900 . ?
C25 C26 1.3900 . ?
C25 H25A 0.9300 . ?
C26 N2 1.3900 . ?
C26 H26A 0.9300 . ?
N2 C27 1.3900 . ?
C27 C28 1.3900 . ?
C27 H27A 0.9300 . ?
C28 H28A 0.9300 . ?
O3 H31W 0.96(4) . ?
O3 H32W 0.96(4) . ?
O4 O4 0.00(3) 1 ?
O4 H41W 0.95(4) . ?
O4 H42W 0.96(4) . ?

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 N1 C5 120.0 . . ?
N1 C1 C2 120.0 . . ?
N1 C1 H1A 120.0 . . ?
C2 C1 H1A 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 C6 122.2(4) . . ?
C4 C3 C6 117.6(4) . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C4 C5 N1 120.0 . . ?
C4 C5 H5A 120.0 . . ?
N1 C5 H5A 120.0 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C6 C11 120.0 . . ?
C7 C6 C3 122.7(4) . . ?
C11 C6 C3 116.9(4) . . ?
C8 C7 C6 120.0 . . ?
C8 C7 O1 118.4(4) . . ?
C6 C7 O1 121.5(4) . . ?
C7 C8 C9 120.0 . . ?
C7 C8 C15 119.1(4) . . ?
C9 C8 C15 120.9(4) . . ?
C8 C9 C10 120.0 . . ?
C8 C9 C13 120.4(5) . . ?
C10 C9 C13 119.5(5) . . ?
C11 C10 C9 120.0 . . ?
C11 C10 C12 117.5(5) . . ?
C9 C10 C12 122.5(5) . . ?
C10 C11 C6 120.0 . . ?
C10 C11 H11A 120.0 . . ?
C6 C11 H11A 120.0 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 120.0 . . ?
C16 C15 C8 118.5(3) . . ?
C20 C15 C8 121.5(3) . . ?
C15 C16 C17 120.0 . . ?
C15 C16 O2 118.9(3) . . ?
C17 C16 O2 121.0(3) . . ?
C16 C17 C18 120.0 . . ?
C16 C17 C24 120.9(3) . . ?
C18 C17 C24 119.0(3) . . ?
C19 C18 C17 120.0 . . ?
C19 C18 H18A 120.0 . . ?
C17 C18 H18A 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 C22 121.8(5) . . ?
C18 C19 C22 118.2(5) . . ?
C19 C20 C15 120.0 . . ?
C19 C20 C21 121.0 . . ?
C15 C20 C21 118.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C28 120.0 . . ?
C25 C24 C17 121.0(4) . . ?
C28 C24 C17 118.9(4) . . ?
C24 C25 C26 120.0 . . ?
C24 C25 H25A 120.0 . . ?
C26 C25 H25A 120.0 . . ?
N2 C26 C25 120.0 . . ?
N2 C26 H26A 120.0 . . ?
C25 C26 H26A 120.0 . . ?
C27 N2 C26 120.0 . . ?
N2 C27 C28 120.0 . . ?
N2 C27 H27A 120.0 . . ?
C28 C27 H27A 120.0 . . ?
C27 C28 C24 120.0 . . ?
C27 C28 H28A 120.0 . . ?
C24 C28 H28A 120.0 . . ?
C7 O1 C14 114.5(6) . . ?
C16 O2 C23 114.4(6) . . ?
H31W O3 H32W 106(6) . . ?
O4 O4 H41W 0(10) 1 . ?
O4 O4 H42W 0(10) 1 . ?
H41W O4 H42W 109(6) . . ?

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
O4 H41W N2 0.95(4) 1.95(5) 2.90(3) 175(11) 1_454
O3 H31W N1 0.96(4) 1.99(6) 2.851(8) 149(9) 1_556
O4 H42W O3 0.96(4) 2.01(7) 2.840(12) 144(10) 2_665
O3 H32W O4 0.96(4) 1.88(4) 2.842(12) 174(17) 1

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.042


# Attachment 'Racemic_1.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 759655'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H28 N2 O2'
_chemical_formula_weight         424.52

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           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   18.2891(18)
_cell_length_b                   6.7249(7)
_cell_length_c                   19.162(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.169(2)
_cell_angle_gamma                90.00
_cell_volume                     2332.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9831
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      27.55

_exptl_crystal_description       rod-like
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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  ?
_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            9831
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         27.55
_reflns_number_total             2664
_reflns_number_gt                1546
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 1990)'
_computing_publication_material  SHELXL-97

_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^)+(0.1140P)^2^+1.2399P] 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         2664
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.2204
_refine_ls_wR_factor_gt          0.1767
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.00836(9) 0.1537(3) 0.16670(9) 0.0429(5) Uani 1 1 d . . .
C2 C -0.03662(13) -0.1236(4) 0.22637(11) 0.0351(6) Uani 1 1 d . . .
C3 C -0.16976(13) -0.0997(4) 0.13827(13) 0.0432(6) Uani 1 1 d . . .
H3A H -0.2146 -0.0929 0.1087 0.052 Uiso 1 1 calc R . .
C4 C -0.11468(13) 0.0333(4) 0.12799(12) 0.0362(6) Uani 1 1 d . . .
C5 C -0.04785(13) 0.0191(4) 0.17317(12) 0.0354(6) Uani 1 1 d . . .
C6 C -0.09349(13) -0.2561(4) 0.23539(12) 0.0375(6) Uani 1 1 d . . .
C7 C -0.12620(13) 0.1835(4) 0.06989(12) 0.0392(6) Uani 1 1 d . . .
C8 C -0.16097(13) -0.2433(4) 0.19100(13) 0.0403(6) Uani 1 1 d . . .
C9 C -0.16106(15) 0.1319(5) 0.00308(13) 0.0479(7) Uani 1 1 d . . .
H9A H -0.1768 0.0019 -0.0062 0.057 Uiso 1 1 calc R . .
C10 C -0.22407(16) -0.3813(5) 0.19883(17) 0.0657(9) Uani 1 1 d . . .
H10A H -0.2665 -0.3438 0.1661 0.099 Uiso 1 1 calc R . .
H10B H -0.2357 -0.3729 0.2460 0.099 Uiso 1 1 calc R . .
H10C H -0.2102 -0.5153 0.1894 0.099 Uiso 1 1 calc R . .
N11 N -0.15182(15) 0.4627(4) -0.04093(13) 0.0600(7) Uani 1 1 d . . .
C12 C -0.08201(17) -0.4153(4) 0.29106(15) 0.0519(7) Uani 1 1 d . . .
H12A H -0.1264 -0.4923 0.2898 0.078 Uiso 1 1 calc R . .
H12B H -0.0701 -0.3547 0.3366 0.078 Uiso 1 1 calc R . .
H12C H -0.0422 -0.5005 0.2823 0.078 Uiso 1 1 calc R . .
C13 C -0.17219(17) 0.2732(5) -0.04919(14) 0.0542(8) Uani 1 1 d . . .
H13A H -0.1955 0.2337 -0.0933 0.065 Uiso 1 1 calc R . .
C14 C -0.10475(17) 0.3792(4) 0.07894(14) 0.0525(7) Uani 1 1 d . . .
H14A H -0.0810 0.4227 0.1224 0.063 Uiso 1 1 calc R . .
C15 C 0.05480(17) 0.0982(6) 0.11623(17) 0.0656(9) Uani 1 1 d . . .
H15A H 0.0919 0.1983 0.1145 0.098 Uiso 1 1 calc R . .
H15B H 0.0257 0.0858 0.0706 0.098 Uiso 1 1 calc R . .
H15C H 0.0781 -0.0267 0.1296 0.098 Uiso 1 1 calc R . .
C16 C -0.11867(19) 0.5107(5) 0.02323(16) 0.0615(9) Uani 1 1 d . . .
H16A H -0.1038 0.6421 0.0311 0.074 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
O1 0.0421(10) 0.0399(10) 0.0456(10) 0.0034(8) 0.0025(7) -0.0082(8)
C2 0.0365(12) 0.0357(13) 0.0319(12) -0.0044(10) 0.0013(9) 0.0006(10)
C3 0.0338(12) 0.0476(16) 0.0452(14) 0.0000(12) -0.0043(10) 0.0004(11)
C4 0.0399(12) 0.0317(13) 0.0352(12) -0.0008(10) -0.0014(10) 0.0036(11)
C5 0.0363(12) 0.0326(13) 0.0357(12) -0.0024(10) 0.0001(9) -0.0026(10)
C6 0.0425(13) 0.0301(13) 0.0391(13) -0.0005(10) 0.0032(10) -0.0003(11)
C7 0.0389(13) 0.0403(15) 0.0374(13) 0.0012(11) 0.0021(10) 0.0062(11)
C8 0.0395(13) 0.0334(14) 0.0473(14) -0.0027(11) 0.0041(11) -0.0049(11)
C9 0.0477(15) 0.0547(18) 0.0392(13) 0.0002(12) -0.0008(11) 0.0053(13)
C10 0.0464(16) 0.074(2) 0.075(2) 0.0099(18) 0.0007(15) -0.0180(16)
N11 0.0640(16) 0.0627(18) 0.0521(14) 0.0168(13) 0.0045(11) 0.0122(14)
C12 0.0564(16) 0.0459(17) 0.0521(15) 0.0118(13) 0.0028(13) -0.0021(14)
C13 0.0548(16) 0.070(2) 0.0359(13) 0.0059(13) 0.0005(11) 0.0097(15)
C14 0.0632(17) 0.0481(18) 0.0440(15) 0.0009(13) -0.0004(13) 0.0058(14)
C15 0.0531(17) 0.073(2) 0.074(2) 0.0040(18) 0.0230(16) -0.0059(16)
C16 0.081(2) 0.0401(17) 0.0614(18) 0.0069(14) 0.0044(16) 0.0073(16)

_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 C5 1.388(3) . ?
O1 C15 1.424(4) . ?
C2 C5 1.394(3) . ?
C2 C6 1.399(3) . ?
C2 C2 1.507(4) 2 ?
C3 C4 1.382(4) . ?
C3 C8 1.390(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.397(3) . ?
C4 C7 1.496(3) . ?
C6 C8 1.399(3) . ?
C6 C12 1.505(3) . ?
C7 C14 1.377(4) . ?
C7 C9 1.390(3) . ?
C8 C10 1.505(4) . ?
C9 C13 1.375(4) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N11 C13 1.331(4) . ?
N11 C16 1.331(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9300 . ?
C14 C16 1.382(4) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9300 . ?

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
C5 O1 C15 114.2(2) . . ?
C5 C2 C6 119.6(2) . . ?
C5 C2 C2 117.8(2) . 2 ?
C6 C2 C2 122.60(19) . 2 ?
C4 C3 C8 122.8(2) . . ?
C4 C3 H3A 118.6 . . ?
C8 C3 H3A 118.6 . . ?
C3 C4 C5 117.3(2) . . ?
C3 C4 C7 121.0(2) . . ?
C5 C4 C7 121.7(2) . . ?
O1 C5 C2 118.69(19) . . ?
O1 C5 C4 119.6(2) . . ?
C2 C5 C4 121.7(2) . . ?
C8 C6 C2 119.5(2) . . ?
C8 C6 C12 119.8(2) . . ?
C2 C6 C12 120.6(2) . . ?
C14 C7 C9 116.1(2) . . ?
C14 C7 C4 123.0(2) . . ?
C9 C7 C4 121.0(2) . . ?
C3 C8 C6 119.0(2) . . ?
C3 C8 C10 119.3(2) . . ?
C6 C8 C10 121.6(2) . . ?
C13 C9 C7 120.0(3) . . ?
C13 C9 H9A 120.0 . . ?
C7 C9 H9A 120.0 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 N11 C16 115.2(3) . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N11 C13 C9 124.4(3) . . ?
N11 C13 H13A 117.8 . . ?
C9 C13 H13A 117.8 . . ?
C7 C14 C16 119.8(3) . . ?
C7 C14 H14A 120.1 . . ?
C16 C14 H14A 120.1 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N11 C16 C14 124.6(3) . . ?
N11 C16 H16A 117.7 . . ?
C14 C16 H16A 117.7 . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.056