# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2004

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Prof Christian Wolf'
_publ_contact_author_address     
;
Department of Chemistry
Georgetown University
Washington
DC 20057
UNITED STATES OF AMERICA
;

_publ_contact_author_email       CW27@GEORGETOWN.EDU

_publ_section_title              
;
A highly congested N,N'-dioxide fluorosensor for
enantioselective recognition of chiral hydrogen bond donors
;
loop_
_publ_author_name
'Christian Wolf'
'Xuefeng Mei'

data_compound_1
_database_code_depnum_ccdc_archive 'CCDC 218159'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,8-Bis(3,3'-bis(3,5-dimethylphenyl)-9,9'-diacridyl)
naphthalene-N,N-dioxide
;
_chemical_name_common            
;1,8-Bis(3,3'-bis(3,5-dimethylphenyl)-9,9'-diacridyl)
naphthalene-N,N-dioxide
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H23 N2 O1.5'
_chemical_formula_sum            'C28 H23 N2 O1.50'
_chemical_formula_weight         411.48

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           Monoclininc
_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                   24.551(2)
_cell_length_b                   13.3883(12)
_cell_length_c                   13.7187(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.204(2)
_cell_angle_gamma                90.00
_cell_volume                     4307.5(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    186(2)
_cell_measurement_reflns_used    6145
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      28.29

_exptl_crystal_description       Prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.46
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1736
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9289
_exptl_absorpt_correction_T_max  0.9647
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      186(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  'SMART platform CCD, Siemens/Bruker'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18167
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         27.00
_reflns_number_total             4690
_reflns_number_gt                3491
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART, Bruker'
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSEED, L. Barbour (1999); http:\x-seed.net'
_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^)+(0.0776P)^2^+3.1342P] 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         4690
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1576
_refine_ls_wR_factor_gt          0.1498
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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
O1 O 0.44954(6) 0.16420(9) 0.09252(10) 0.0287(3) Uani 1 1 d . . .
O1S O 0.5000 0.30691(17) 0.2500 0.0457(6) Uani 1 2 d S . .
N1 N 0.46424(6) 0.07004(11) 0.10616(11) 0.0223(3) Uani 1 1 d . . .
N1S N 0.2704(2) -0.2337(3) 0.2601(4) 0.152(2) Uani 1 1 d . . .
C1 C 0.39233(8) -0.17373(13) 0.09308(14) 0.0237(4) Uani 1 1 d . . .
H1 H 0.4008 -0.2429 0.1029 0.028 Uiso 1 1 calc R . .
C2 C 0.33685(8) -0.14385(15) 0.06238(15) 0.0271(4) Uani 1 1 d . . .
H2 H 0.3075 -0.1927 0.0498 0.032 Uiso 1 1 calc R . .
C3 C 0.32187(8) -0.04078(14) 0.04868(14) 0.0256(4) Uani 1 1 d . . .
C4 C 0.36456(8) 0.02843(14) 0.06341(14) 0.0245(4) Uani 1 1 d . . .
H4 H 0.3553 0.0973 0.0540 0.029 Uiso 1 1 calc R . .
C5 C 0.56252(8) 0.11900(14) 0.14317(14) 0.0275(4) Uani 1 1 d . . .
H5 H 0.5514 0.1870 0.1320 0.033 Uiso 1 1 calc R . .
C6 C 0.61884(8) 0.09356(15) 0.17006(15) 0.0303(4) Uani 1 1 d . . .
H6 H 0.6469 0.1444 0.1783 0.036 Uiso 1 1 calc R . .
C7 C 0.63597(8) -0.00700(15) 0.18572(15) 0.0286(4) Uani 1 1 d . . .
H7 H 0.6753 -0.0234 0.2034 0.034 Uiso 1 1 calc R . .
C8 C 0.59668(8) -0.08087(14) 0.17581(13) 0.0246(4) Uani 1 1 d . . .
H8 H 0.6090 -0.1483 0.1867 0.030 Uiso 1 1 calc R . .
C9 C 0.49569(7) -0.13254(13) 0.14331(13) 0.0205(4) Uani 1 1 d . . .
C10 C 0.43791(7) -0.10375(13) 0.11083(13) 0.0210(4) Uani 1 1 d . . .
C11 C 0.42239(7) -0.00165(13) 0.09256(13) 0.0215(4) Uani 1 1 d . . .
C12 C 0.52081(7) 0.04361(13) 0.13209(13) 0.0216(4) Uani 1 1 d . . .
C13 C 0.53704(7) -0.05877(13) 0.14929(13) 0.0206(4) Uani 1 1 d . . .
C14 C 0.50985(7) -0.24070(13) 0.16421(13) 0.0205(4) Uani 1 1 d . . .
C15 C 0.52524(8) -0.29483(14) 0.09134(14) 0.0249(4) Uani 1 1 d . . .
H15 H 0.5333 -0.2610 0.0363 0.030 Uiso 1 1 calc R . .
C16 C 0.52926(8) -0.39981(14) 0.09712(15) 0.0284(4) Uani 1 1 d . . .
H16 H 0.5417 -0.4356 0.0479 0.034 Uiso 1 1 calc R . .
C17 C 0.51543(8) -0.45038(14) 0.17256(15) 0.0266(4) Uani 1 1 d . . .
H17 H 0.5161 -0.5213 0.1734 0.032 Uiso 1 1 calc R . .
C18 C 0.5000 -0.39741(19) 0.2500 0.0223(5) Uani 1 2 d S . .
C19 C 0.5000 -0.29095(18) 0.2500 0.0196(5) Uani 1 2 d S . .
C20 C 0.26083(8) -0.01126(15) 0.02077(15) 0.0288(4) Uani 1 1 d . . .
C21 C 0.24059(9) 0.07317(16) -0.03809(16) 0.0333(5) Uani 1 1 d . . .
H21 H 0.2665 0.1140 -0.0597 0.040 Uiso 1 1 calc R . .
C22 C 0.18290(9) 0.09879(17) -0.06591(17) 0.0383(5) Uani 1 1 d . . .
C23 C 0.14591(9) 0.03786(17) -0.03314(17) 0.0384(5) Uani 1 1 d . . .
H23 H 0.1065 0.0539 -0.0530 0.046 Uiso 1 1 calc R . .
C24 C 0.16464(8) -0.04564(16) 0.02761(16) 0.0345(5) Uani 1 1 d . . .
C25 C 0.22232(8) -0.06945(16) 0.05368(16) 0.0315(5) Uani 1 1 d . . .
H25 H 0.2359 -0.1266 0.0948 0.038 Uiso 1 1 calc R . .
C26 C 0.12489(9) -0.10766(18) 0.06759(19) 0.0429(6) Uani 1 1 d . . .
H26A H 0.1419 -0.1736 0.0878 0.064 Uiso 1 1 calc R . .
H26B H 0.0885 -0.1155 0.0141 0.064 Uiso 1 1 calc R . .
H26C H 0.1184 -0.0744 0.1268 0.064 Uiso 1 1 calc R . .
C27 C 0.16129(11) 0.1898(2) -0.1312(2) 0.0564(7) Uani 1 1 d . . .
H27A H 0.1933 0.2232 -0.1468 0.085 Uiso 0.50 1 calc PR . .
H27B H 0.1435 0.2359 -0.0942 0.085 Uiso 0.50 1 calc PR . .
H27C H 0.1331 0.1693 -0.1949 0.085 Uiso 0.50 1 calc PR . .
H27D H 0.1200 0.1957 -0.1438 0.085 Uiso 0.50 1 calc PR . .
H27E H 0.1697 0.1830 -0.1964 0.085 Uiso 0.50 1 calc PR . .
H27F H 0.1801 0.2497 -0.0957 0.085 Uiso 0.50 1 calc PR . .
C1S C 0.32050(16) -0.3952(3) 0.2436(3) 0.0828(11) Uani 1 1 d . . .
H1S1 H 0.3127 -0.4124 0.1713 0.124 Uiso 1 1 calc R . .
H1S2 H 0.3073 -0.4493 0.2790 0.124 Uiso 1 1 calc R . .
H1S3 H 0.3616 -0.3857 0.2743 0.124 Uiso 1 1 calc R . .
C2S C 0.29164(13) -0.3063(3) 0.2524(3) 0.0696(9) Uani 1 1 d . . .
H1S H 0.4825(13) 0.261(2) 0.203(2) 0.078(10) Uiso 1 1 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 0.0315(7) 0.0184(7) 0.0347(8) 0.0041(5) 0.0074(6) 0.0039(6)
O1S 0.0533(15) 0.0257(11) 0.0538(15) 0.000 0.0093(12) 0.000
N1 0.0261(8) 0.0207(8) 0.0203(8) 0.0020(6) 0.0072(6) 0.0026(6)
N1S 0.163(4) 0.126(3) 0.220(5) 0.086(3) 0.139(4) 0.074(3)
C1 0.0250(9) 0.0203(9) 0.0251(9) -0.0001(7) 0.0062(7) 0.0012(7)
C2 0.0223(9) 0.0281(10) 0.0298(10) -0.0022(8) 0.0062(8) -0.0025(8)
C3 0.0216(9) 0.0312(10) 0.0229(9) -0.0001(7) 0.0048(7) 0.0044(8)
C4 0.0257(9) 0.0243(9) 0.0230(9) 0.0018(7) 0.0064(7) 0.0050(8)
C5 0.0317(10) 0.0239(9) 0.0275(10) 0.0016(7) 0.0095(8) -0.0022(8)
C6 0.0273(10) 0.0338(11) 0.0301(11) -0.0012(8) 0.0089(8) -0.0083(8)
C7 0.0223(9) 0.0365(11) 0.0274(10) 0.0000(8) 0.0079(8) -0.0018(8)
C8 0.0239(9) 0.0285(10) 0.0222(9) 0.0019(7) 0.0077(7) 0.0018(8)
C9 0.0221(9) 0.0240(9) 0.0158(8) 0.0001(7) 0.0062(7) 0.0014(7)
C10 0.0217(9) 0.0233(9) 0.0184(9) 0.0005(7) 0.0065(7) 0.0021(7)
C11 0.0226(9) 0.0238(9) 0.0180(9) 0.0001(7) 0.0059(7) 0.0011(7)
C12 0.0232(9) 0.0249(9) 0.0173(9) 0.0001(7) 0.0068(7) 0.0001(7)
C13 0.0226(9) 0.0238(9) 0.0159(8) 0.0013(7) 0.0062(7) 0.0005(7)
C14 0.0155(8) 0.0211(9) 0.0238(9) 0.0016(7) 0.0044(7) 0.0010(7)
C15 0.0241(9) 0.0279(10) 0.0243(9) -0.0001(7) 0.0096(7) 0.0021(8)
C16 0.0277(10) 0.0286(10) 0.0306(10) -0.0055(8) 0.0112(8) 0.0044(8)
C17 0.0244(9) 0.0181(9) 0.0367(11) -0.0039(7) 0.0080(8) 0.0006(7)
C18 0.0165(12) 0.0221(13) 0.0271(13) 0.000 0.0046(10) 0.000
C19 0.0144(11) 0.0204(12) 0.0223(12) 0.000 0.0029(9) 0.000
C20 0.0229(9) 0.0314(10) 0.0297(10) -0.0040(8) 0.0041(8) 0.0039(8)
C21 0.0276(10) 0.0363(11) 0.0347(11) 0.0005(9) 0.0072(8) 0.0067(9)
C22 0.0309(11) 0.0410(12) 0.0402(12) -0.0007(10) 0.0063(9) 0.0148(10)
C23 0.0235(10) 0.0462(13) 0.0431(13) -0.0079(10) 0.0059(9) 0.0120(10)
C24 0.0248(10) 0.0400(12) 0.0385(12) -0.0104(9) 0.0089(9) 0.0031(9)
C25 0.0250(10) 0.0329(11) 0.0354(11) -0.0021(8) 0.0069(8) 0.0041(8)
C26 0.0273(11) 0.0451(13) 0.0571(15) -0.0094(11) 0.0137(10) 0.0001(10)
C27 0.0426(14) 0.0567(16) 0.0659(17) 0.0127(13) 0.0097(12) 0.0240(12)
C1S 0.102(3) 0.074(2) 0.061(2) 0.0003(16) 0.0055(18) 0.027(2)
C2S 0.0560(18) 0.072(2) 0.090(2) 0.0336(18) 0.0357(17) 0.0167(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 N1 1.3094(19) . ?
N1 C12 1.374(2) . ?
N1 C11 1.378(2) . ?
N1S C2S 1.123(5) . ?
C1 C2 1.361(3) . ?
C1 C10 1.424(3) . ?
C2 C3 1.426(3) . ?
C3 C4 1.368(3) . ?
C3 C20 1.486(3) . ?
C4 C11 1.415(3) . ?
C5 C6 1.365(3) . ?
C5 C12 1.414(3) . ?
C6 C7 1.408(3) . ?
C7 C8 1.360(3) . ?
C8 C13 1.431(2) . ?
C9 C13 1.401(2) . ?
C9 C10 1.409(2) . ?
C9 C14 1.497(2) . ?
C10 C11 1.421(2) . ?
C12 C13 1.427(2) . ?
C14 C15 1.375(2) . ?
C14 C19 1.437(2) . ?
C15 C16 1.410(3) . ?
C16 C17 1.361(3) . ?
C17 C18 1.419(2) . ?
C18 C17 1.419(2) 2_655 ?
C18 C19 1.425(3) . ?
C19 C14 1.437(2) 2_655 ?
C20 C21 1.393(3) . ?
C20 C25 1.399(3) . ?
C21 C22 1.396(3) . ?
C22 C23 1.390(3) . ?
C22 C27 1.512(3) . ?
C23 C24 1.389(3) . ?
C24 C25 1.391(3) . ?
C24 C26 1.503(3) . ?
C1S C2S 1.408(5) . ?

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
O1 N1 C12 119.98(15) . . ?
O1 N1 C11 119.24(14) . . ?
C12 N1 C11 120.78(15) . . ?
C2 C1 C10 121.55(17) . . ?
C1 C2 C3 121.36(17) . . ?
C4 C3 C2 118.65(17) . . ?
C4 C3 C20 121.85(17) . . ?
C2 C3 C20 119.49(17) . . ?
C3 C4 C11 120.63(17) . . ?
C6 C5 C12 119.65(18) . . ?
C5 C6 C7 120.86(18) . . ?
C8 C7 C6 120.61(18) . . ?
C7 C8 C13 121.13(18) . . ?
C13 C9 C10 118.02(16) . . ?
C13 C9 C14 123.20(16) . . ?
C10 C9 C14 118.70(15) . . ?
C9 C10 C11 120.74(16) . . ?
C9 C10 C1 122.73(16) . . ?
C11 C10 C1 116.52(16) . . ?
N1 C11 C4 119.06(16) . . ?
N1 C11 C10 119.73(16) . . ?
C4 C11 C10 121.19(16) . . ?
N1 C12 C5 119.24(16) . . ?
N1 C12 C13 120.09(15) . . ?
C5 C12 C13 120.66(16) . . ?
C9 C13 C12 120.35(16) . . ?
C9 C13 C8 122.55(16) . . ?
C12 C13 C8 117.07(16) . . ?
C15 C14 C19 119.85(17) . . ?
C15 C14 C9 117.95(16) . . ?
C19 C14 C9 121.61(16) . . ?
C14 C15 C16 120.94(17) . . ?
C17 C16 C15 120.65(17) . . ?
C16 C17 C18 120.17(18) . . ?
C17 C18 C17 120.0(2) 2_655 . ?
C17 C18 C19 119.99(12) 2_655 . ?
C17 C18 C19 119.99(12) . . ?
C18 C19 C14 117.92(11) . 2_655 ?
C18 C19 C14 117.92(11) . . ?
C14 C19 C14 124.2(2) 2_655 . ?
C21 C20 C25 118.68(18) . . ?
C21 C20 C3 121.66(18) . . ?
C25 C20 C3 119.66(18) . . ?
C20 C21 C22 121.1(2) . . ?
C23 C22 C21 118.3(2) . . ?
C23 C22 C27 121.1(2) . . ?
C21 C22 C27 120.6(2) . . ?
C24 C23 C22 122.29(19) . . ?
C23 C24 C25 118.0(2) . . ?
C23 C24 C26 121.88(19) . . ?
C25 C24 C26 120.1(2) . . ?
C24 C25 C20 121.5(2) . . ?
N1S C2S C1S 177.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.051

#===END