Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2002

data_ijmm 
_database_code_CSD                  186682

_journal_coden_Cambridge      182

_publ_requested_journal       'Chemical Communications'

loop_
_publ_author_name
'Scott, Peter'
'Clarke, Adam J.'
'Deeth, Robert J.'
'Munslow, Ian J.'
'Westmoreland, Ian'

_publ_contact_author_name     	'Chemical Communications'  
_publ_contact_author_address 
;
Chemistry
University of Warwick
Gibbett Hill Rd
Coventry
CV4 7AL
UNITED KINGDOM
;

_publ_contact_author_email       'PETER.SCOTT@WARWICK.AC.UK'

_publ_section_title		
;
Efficient predetermination of chirality-at-zirconium
;

_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
'C46 H62 N2 O2 Zr' 
_chemical_formula_weight          766.20 

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' 
'Zr'  'Zr'  -2.9673   0.5597 
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

_symmetry_cell_setting            Tetragonal
_symmetry_space_group_name_H-M    P4(3)2(1)2

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

_cell_length_a                    13.5618(2) 
_cell_length_b                    13.5618(2) 
_cell_length_c                    22.9202(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      4215.54(14) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     180(2) 
_cell_measurement_reflns_used     6141
_cell_measurement_theta_min       1.74
_cell_measurement_theta_max       29.23

_exptl_crystal_description        Block
_exptl_crystal_colour             'Pale Yellow'
_exptl_crystal_size_max           0.21
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.17
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.207 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1632 
_exptl_absorpt_coefficient_mu     0.298 
_exptl_absorpt_correction_type    SADABS
_exptl_absorpt_correction_T_min   0.749694
_exptl_absorpt_correction_T_max   0.927998
_exptl_absorpt_process_details    'SADABS (Sheldrick, 1996)' 

_exptl_special_details 
; 
? 
; 

_diffrn_ambient_temperature       180(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   'Siemens SMART diffractometer' 
_diffrn_measurement_method        '\w scans' 
_diffrn_detector_area_resol_mean  8.192 
_diffrn_standards_number          ?  
_diffrn_standards_interval_count  ?  
_diffrn_standards_interval_time   ?  
_diffrn_standards_decay_%         nil 
_diffrn_reflns_number             27767 
_diffrn_reflns_av_R_equivalents   0.1428 
_diffrn_reflns_av_sigmaI/netI     0.1192 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        18 
_diffrn_reflns_limit_k_min        -18 
_diffrn_reflns_limit_k_max        18 
_diffrn_reflns_limit_l_min        -31 
_diffrn_reflns_limit_l_max        31 
_diffrn_reflns_theta_min          1.74 
_diffrn_reflns_theta_max          29.23 
_reflns_number_total              5390 
_reflns_number_gt                 3477 
_reflns_threshold_expression      >2sigma(I) 

_computing_data_collection        'SMART (Siemens, 1994)' 
_computing_cell_refinement        'SAINT (Siemens, 1995)' 
_computing_data_reduction         'SAINT (Siemens, 1995)' 
_computing_structure_solution     'SHELXTL (Sheldrick, 1997)' 
_computing_structure_refinement   'SHELXTL (Sheldrick, 1997)'  
_computing_molecular_graphics     'SHELXTL (Sheldrick, 1997)' 
_computing_publication_material   'SHELXTL (Sheldrick, 1997)' 

_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^)+(0.0317P)^2^+4.3403P] 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    0.00(6) 
_refine_ls_number_reflns          5390 
_refine_ls_number_parameters      235 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1351 
_refine_ls_R_factor_gt            0.0636 
_refine_ls_wR_factor_ref          0.1239 
_refine_ls_wR_factor_gt           0.0994 
_refine_ls_goodness_of_fit_ref    1.106 
_refine_ls_restrained_S_all       1.106 
_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 
Zr1 Zr 0.45006(3) 0.45006(3) 0.0000 0.01997(13) Uani 1 2 d S . . 
O1 O 0.4045(2) 0.58565(19) 0.01307(11) 0.0237(6) Uani 1 1 d . . . 
N1 N 0.5490(3) 0.4677(2) 0.09069(13) 0.0231(7) Uani 1 1 d . . . 
C1 C 0.6634(3) 0.3805(3) 0.02556(18) 0.0238(10) Uani 1 1 d . . . 
C2 C 0.6743(3) 0.2682(3) 0.0299(2) 0.0303(11) Uani 1 1 d . . . 
H2A H 0.7233 0.2523 0.0605 0.036 Uiso 1 1 calc R . . 
H2B H 0.6104 0.2393 0.0418 0.036 Uiso 1 1 calc R . . 
C3 C 0.7069(4) 0.2216(4) -0.0276(2) 0.0345(12) Uani 1 1 d . . . 
H3A H 0.6555 0.2354 -0.0578 0.041 Uiso 1 1 calc R . . 
C4 C 0.8039(4) 0.2684(4) -0.0471(2) 0.0386(13) Uani 1 1 d . . . 
H4A H 0.8560 0.2526 -0.0184 0.046 Uiso 1 1 calc R . . 
H4B H 0.8237 0.2398 -0.0851 0.046 Uiso 1 1 calc R . . 
C5 C 0.7951(3) 0.3797(4) -0.0532(2) 0.0360(12) Uani 1 1 d . . . 
H5A H 0.7469 0.3955 -0.0842 0.043 Uiso 1 1 calc R . . 
H5B H 0.8598 0.4073 -0.0649 0.043 Uiso 1 1 calc R . . 
C6 C 0.7620(3) 0.4276(3) 0.0045(2) 0.0284(10) Uani 1 1 d . . . 
H6A H 0.8128 0.4095 0.0342 0.034 Uiso 1 1 calc R . . 
C7 C 0.7588(3) 0.5427(3) 0.0029(2) 0.0338(10) Uani 1 1 d . . . 
H7A H 0.7013 0.5636 0.0272 0.041 Uiso 1 1 calc R . . 
C8 C 0.8509(4) 0.5851(4) 0.0316(3) 0.0623(19) Uani 1 1 d . . . 
H8A H 0.8464 0.6573 0.0322 0.093 Uiso 1 1 calc R . . 
H8B H 0.9093 0.5651 0.0094 0.093 Uiso 1 1 calc R . . 
H8C H 0.8561 0.5604 0.0716 0.093 Uiso 1 1 calc R . . 
C9 C 0.7446(4) 0.5875(4) -0.0571(2) 0.0508(15) Uani 1 1 d . . . 
H9A H 0.7374 0.6591 -0.0535 0.076 Uiso 1 1 calc R . . 
H9B H 0.6852 0.5598 -0.0751 0.076 Uiso 1 1 calc R . . 
H9C H 0.8020 0.5724 -0.0815 0.076 Uiso 1 1 calc R . . 
C10 C 0.7167(4) 0.1097(4) -0.0205(3) 0.0512(16) Uani 1 1 d . . . 
H10A H 0.6527 0.0817 -0.0097 0.077 Uiso 1 1 calc R . . 
H10B H 0.7650 0.0952 0.0102 0.077 Uiso 1 1 calc R . . 
H10C H 0.7388 0.0807 -0.0574 0.077 Uiso 1 1 calc R . . 
C11 C 0.6370(3) 0.4219(3) 0.08548(19) 0.0244(11) Uani 1 1 d . . . 
C12 C 0.7013(3) 0.4125(3) 0.13231(19) 0.0297(11) Uani 1 1 d . . . 
H12A H 0.7610 0.3767 0.1280 0.036 Uiso 1 1 calc R . . 
C13 C 0.6783(4) 0.4549(4) 0.1847(2) 0.0367(11) Uani 1 1 d . . . 
H13A H 0.7220 0.4499 0.2169 0.044 Uiso 1 1 calc R . . 
C14 C 0.5904(4) 0.5051(3) 0.1896(2) 0.0319(11) Uani 1 1 d . . . 
H14A H 0.5740 0.5371 0.2251 0.038 Uiso 1 1 calc R . . 
C15 C 0.5257(3) 0.5090(3) 0.14259(17) 0.0253(10) Uani 1 1 d . . . 
C16 C 0.4285(3) 0.5604(4) 0.14972(18) 0.0342(11) Uani 1 1 d . . . 
H16A H 0.4026 0.5785 0.1113 0.051 Uiso 1 1 calc R . . 
H16B H 0.4376 0.6200 0.1733 0.051 Uiso 1 1 calc R . . 
H16C H 0.3818 0.5162 0.1693 0.051 Uiso 1 1 calc R . . 
C17 C 0.3607(4) 0.3547(3) 0.06787(19) 0.0282(10) Uani 1 1 d . . . 
H17A H 0.3492 0.3948 0.1033 0.034 Uiso 1 1 calc R . . 
H17B H 0.2956 0.3384 0.0509 0.034 Uiso 1 1 calc R . . 
C18 C 0.4107(3) 0.2622(3) 0.0849(2) 0.0293(11) Uani 1 1 d . . . 
C19 C 0.4641(4) 0.2534(4) 0.1376(2) 0.0362(12) Uani 1 1 d . . . 
H19A H 0.4665 0.3079 0.1636 0.043 Uiso 1 1 calc R . . 
C20 C 0.5129(4) 0.1675(4) 0.1524(2) 0.0493(16) Uani 1 1 d . . . 
H20A H 0.5480 0.1639 0.1882 0.059 Uiso 1 1 calc R . . 
C21 C 0.5112(4) 0.0865(4) 0.1154(3) 0.0515(16) Uani 1 1 d . . . 
H21A H 0.5450 0.0276 0.1256 0.062 Uiso 1 1 calc R . . 
C22 C 0.4598(4) 0.0928(4) 0.0638(3) 0.0460(14) Uani 1 1 d . . . 
H22A H 0.4580 0.0379 0.0380 0.055 Uiso 1 1 calc R . . 
C23 C 0.4113(4) 0.1779(3) 0.0494(2) 0.0336(12) Uani 1 1 d . . . 
H23A H 0.3762 0.1800 0.0135 0.040 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 
Zr1 0.01838(17) 0.01838(17) 0.0232(3) -0.0001(2) 0.0001(2) -0.0009(3) 
O1 0.0326(17) 0.0143(15) 0.0242(16) 0.0024(12) 0.0020(13) 0.0003(11) 
N1 0.0244(19) 0.022(2) 0.0233(16) -0.0007(13) 0.0020(17) -0.0050(17) 
C1 0.024(2) 0.023(2) 0.024(2) 0.0022(18) 0.0006(19) 0.0040(19) 
C2 0.027(3) 0.030(3) 0.034(3) -0.005(2) 0.001(2) 0.001(2) 
C3 0.030(3) 0.035(3) 0.038(3) -0.011(2) -0.002(2) 0.006(2) 
C4 0.031(3) 0.045(3) 0.040(3) -0.007(2) 0.006(2) 0.011(2) 
C5 0.022(3) 0.045(3) 0.041(3) -0.001(3) 0.011(2) -0.002(2) 
C6 0.017(2) 0.036(3) 0.032(3) -0.003(2) 0.000(2) -0.0002(17) 
C7 0.028(2) 0.033(2) 0.039(3) -0.001(3) 0.007(2) -0.004(2) 
C8 0.052(4) 0.052(4) 0.083(5) -0.011(3) -0.017(3) -0.016(3) 
C9 0.056(4) 0.039(3) 0.058(4) 0.007(3) 0.002(3) -0.008(3) 
C10 0.055(4) 0.033(3) 0.067(4) -0.011(3) 0.008(3) 0.008(3) 
C11 0.022(2) 0.023(2) 0.028(2) 0.0027(18) -0.0032(19) -0.0007(18) 
C12 0.028(3) 0.032(3) 0.029(3) -0.001(2) -0.008(2) 0.003(2) 
C13 0.040(3) 0.040(3) 0.030(3) 0.000(3) -0.008(2) 0.000(3) 
C14 0.039(3) 0.031(3) 0.026(2) -0.001(2) 0.000(2) -0.008(2) 
C15 0.030(3) 0.022(2) 0.024(2) 0.0005(18) 0.0049(18) -0.0042(18) 
C16 0.039(3) 0.034(3) 0.030(2) -0.003(2) 0.008(2) 0.004(2) 
C17 0.029(3) 0.021(3) 0.035(2) 0.002(2) 0.004(2) -0.0049(18) 
C18 0.030(3) 0.024(3) 0.035(3) 0.004(2) 0.008(2) -0.009(2) 
C19 0.043(3) 0.033(3) 0.033(3) 0.002(2) 0.004(2) -0.002(3) 
C20 0.061(4) 0.049(4) 0.038(3) 0.015(3) -0.001(3) 0.002(3) 
C21 0.057(4) 0.028(3) 0.070(4) 0.014(3) 0.012(3) 0.010(3) 
C22 0.054(4) 0.028(3) 0.057(4) 0.004(2) 0.015(3) -0.005(3) 
C23 0.035(3) 0.025(3) 0.041(3) 0.003(2) 0.006(2) -0.005(2) 

_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 
Zr1 O1 1.963(2) . ? 
Zr1 O1 1.963(2) 7 ? 
Zr1 C17 2.358(4) 7 ? 
Zr1 C17 2.358(4) . ? 
Zr1 N1 2.485(3) . ? 
Zr1 N1 2.485(3) 7 ? 
O1 C1 1.415(5) 7 ? 
N1 C11 1.351(5) . ? 
N1 C15 1.352(5) . ? 
C1 O1 1.415(5) 7 ? 
C1 C11 1.526(6) . ? 
C1 C2 1.534(6) . ? 
C1 C6 1.558(6) . ? 
C2 C3 1.526(6) . ? 
C3 C4 1.528(6) . ? 
C3 C10 1.532(7) . ? 
C4 C5 1.521(7) . ? 
C5 C6 1.539(7) . ? 
C6 C7 1.562(6) . ? 
C7 C9 1.517(7) . ? 
C7 C8 1.523(7) . ? 
C11 C12 1.389(6) . ? 
C12 C13 1.367(6) . ? 
C13 C14 1.376(6) . ? 
C14 C15 1.390(6) . ? 
C15 C16 1.500(6) . ? 
C17 C18 1.479(7) . ? 
C18 C23 1.404(6) . ? 
C18 C19 1.414(7) . ? 
C19 C20 1.381(7) . ? 
C20 C21 1.388(7) . ? 
C21 C22 1.377(8) . ? 
C22 C23 1.369(7) . ? 

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 Zr1 O1 127.83(18) . 7 ? 
O1 Zr1 C17 114.16(15) . 7 ? 
O1 Zr1 C17 104.54(15) 7 7 ? 
O1 Zr1 C17 104.54(15) . . ? 
O1 Zr1 C17 114.16(15) 7 . ? 
C17 Zr1 C17 82.6(2) 7 . ? 
O1 Zr1 N1 87.27(11) . . ? 
O1 Zr1 N1 69.66(11) 7 . ? 
C17 Zr1 N1 153.78(14) 7 . ? 
C17 Zr1 N1 77.17(13) . . ? 
O1 Zr1 N1 69.66(11) . 7 ? 
O1 Zr1 N1 87.27(11) 7 7 ? 
C17 Zr1 N1 77.17(13) 7 7 ? 
C17 Zr1 N1 153.78(14) . 7 ? 
N1 Zr1 N1 126.58(15) . 7 ? 
C1 O1 Zr1 132.5(2) 7 . ? 
C11 N1 C15 118.3(4) . . ? 
C11 N1 Zr1 111.0(2) . . ? 
C15 N1 Zr1 130.5(3) . . ? 
O1 C1 C11 107.7(3) 7 . ? 
O1 C1 C2 109.9(3) 7 . ? 
C11 C1 C2 109.2(3) . . ? 
O1 C1 C6 110.6(3) 7 . ? 
C11 C1 C6 109.3(3) . . ? 
C2 C1 C6 110.1(4) . . ? 
C3 C2 C1 112.5(4) . . ? 
C2 C3 C4 109.3(4) . . ? 
C2 C3 C10 110.1(4) . . ? 
C4 C3 C10 111.5(4) . . ? 
C5 C4 C3 111.8(4) . . ? 
C4 C5 C6 111.3(4) . . ? 
C5 C6 C1 110.1(4) . . ? 
C5 C6 C7 114.2(4) . . ? 
C1 C6 C7 113.2(3) . . ? 
C9 C7 C8 110.1(4) . . ? 
C9 C7 C6 115.1(4) . . ? 
C8 C7 C6 110.2(4) . . ? 
N1 C11 C12 121.9(4) . . ? 
N1 C11 C1 117.2(4) . . ? 
C12 C11 C1 120.9(4) . . ? 
C13 C12 C11 119.8(4) . . ? 
C12 C13 C14 118.5(4) . . ? 
C13 C14 C15 120.2(4) . . ? 
N1 C15 C14 121.2(4) . . ? 
N1 C15 C16 119.6(4) . . ? 
C14 C15 C16 119.2(4) . . ? 
C18 C17 Zr1 113.9(3) . . ? 
C23 C18 C19 115.1(4) . . ? 
C23 C18 C17 122.7(4) . . ? 
C19 C18 C17 122.2(4) . . ? 
C20 C19 C18 121.8(5) . . ? 
C19 C20 C21 120.6(5) . . ? 
C22 C21 C20 119.0(5) . . ? 
C23 C22 C21 120.1(5) . . ? 
C22 C23 C18 123.4(5) . . ? 

_diffrn_measured_fraction_theta_max    0.962 
_diffrn_reflns_theta_full              29.23 
_diffrn_measured_fraction_theta_full   0.962 
_refine_diff_density_max    0.394 
_refine_diff_density_min   -0.624 
_refine_diff_density_rms    0.093