# Supplementary Material (ESI) for ChemComm
# This journal is © The Royal Society of Chemistry 1999
# CCDC Number: 182/1447
 
data_aug698 
  
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             '[C2tBu2P2NPh]' 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C16 H23 N P2' 
_chemical_formula_weight          291.29 
_chemical_melting_point           ? 
_chemical_compound_source         ? 
  
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' 
 'P'  'P'   0.1023   0.0942 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_symmetry_cell_setting            orthorhombic 
_symmetry_space_group_name_H-M    Pna2(1) 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, z+1/2' 
 '-x+1/2, y+1/2, z+1/2' 
 'x+1/2, -y+1/2, z' 
  
_cell_length_a                    26.960(5) 
_cell_length_b                    5.916(2) 
_cell_length_c                    10.299(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      1642.6(8) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     25 
_cell_measurement_theta_min       7 
_cell_measurement_theta_max       10 
  
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           0.10 
_exptl_crystal_size_mid           0.10 
_exptl_crystal_size_min           0.05 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.178 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              624 
_exptl_absorpt_coefficient_mu     0.253 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
  
_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        ' Enraf-Nonius CAD4' 
_diffrn_measurement_method        \w--2\q 
_diffrn_standards_number          2 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   120 
_diffrn_standards_decay_%         0 
_diffrn_reflns_number             1071 
_diffrn_reflns_av_R_equivalents   0.0000 
_diffrn_reflns_av_sigmaI/netI     0.0751 
_diffrn_reflns_limit_h_min        0 
_diffrn_reflns_limit_h_max        28 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        6 
_diffrn_reflns_limit_l_min        0 
_diffrn_reflns_limit_l_max        10 
_diffrn_reflns_theta_min          2.49 
_diffrn_reflns_theta_max          21.96 
_reflns_number_total              1071 
_reflns_number_observed           859 
_reflns_observed_criterion        >2sigma(I) 
  
_computing_data_collection        'Enraf-Nonius CAD4' 
_computing_cell_refinement        'Enraf-Nonius CAD4' 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     'CAMERON (Watkin and Pearce,1993)' 
_computing_publication_material   SHELXL-93 
  
_refine_special_details 
; 
 Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ 
 or flagged by the user for potential systematic errors.  Weighted R-factors 
 wR and all goodnesses 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 observed criterion 
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0168P)^2^+2.1122P] 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     riding 
_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    0.10(28) 
_refine_ls_number_reflns          1071 
_refine_ls_number_parameters      172 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0690 
_refine_ls_R_factor_obs           0.0444 
_refine_ls_wR_factor_all          0.1058 
_refine_ls_wR_factor_obs          0.0860 
_refine_ls_goodness_of_fit_all    1.110 
_refine_ls_goodness_of_fit_obs    1.031 
_refine_ls_restrained_S_all       1.110 
_refine_ls_restrained_S_obs       1.030 
_refine_ls_shift/esd_max          0.000 
_refine_ls_shift/esd_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_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
P1 P 0.10948(8) 0.3976(4) 0.0862(2) 0.0270(6) Uani 1 d . . 
P2 P 0.17537(8) 0.4750(4) -0.1340(2) 0.0264(6) Uani 1 d . . 
N N 0.1214(2) 0.3294(10) -0.1622(6) 0.024(2) Uani 1 d . . 
C1 C 0.1646(3) 0.5130(14) 0.0269(7) 0.021(2) Uani 1 d . . 
C2 C 0.0896(3) 0.2880(14) -0.0617(8) 0.026(2) Uani 1 d . . 
C3 C 0.2020(3) 0.6339(13) 0.1164(7) 0.020(2) Uani 1 d . . 
C4 C 0.2396(3) 0.7686(16) 0.0363(9) 0.042(3) Uani 1 d . . 
H4A H 0.2576(3) 0.6660(16) -0.0216(9) 0.063 Uiso 1 calc R . 
H4B H 0.2632(3) 0.8434(16) 0.0948(9) 0.063 Uiso 1 calc R . 
H4C H 0.2222(3) 0.8827(16) -0.0154(9) 0.063 Uiso 1 calc R . 
C5 C 0.1746(4) 0.7965(16) 0.2056(10) 0.051(3) Uani 1 d . . 
H5A H 0.1503(4) 0.7124(16) 0.2575(10) 0.077 Uiso 1 calc R . 
H5B H 0.1573(4) 0.9105(16) 0.1532(10) 0.077 Uiso 1 calc R . 
H5C H 0.1983(4) 0.8712(16) 0.2634(10) 0.077 Uiso 1 calc R . 
C6 C 0.2290(3) 0.4533(16) 0.1968(9) 0.049(3) Uani 1 d . . 
H6A H 0.2466(3) 0.3497(16) 0.1386(9) 0.073 Uiso 1 calc R . 
H6B H 0.2048(3) 0.3685(16) 0.2484(9) 0.073 Uiso 1 calc R . 
H6C H 0.2529(3) 0.5266(16) 0.2549(9) 0.073 Uiso 1 calc R . 
C7 C 0.0401(3) 0.1623(14) -0.0751(8) 0.028(2) Uani 1 d . . 
C8 C 0.0068(3) 0.2782(16) -0.1784(8) 0.039(3) Uani 1 d . . 
H8A H 0.0021(3) 0.4375(16) -0.1553(8) 0.058 Uiso 1 calc R . 
H8B H -0.0255(3) 0.2022(16) -0.1815(8) 0.058 Uiso 1 calc R . 
H8C H 0.0228(3) 0.2681(16) -0.2637(8) 0.058 Uiso 1 calc R . 
C9 C 0.0478(3) -0.0833(13) -0.1091(10) 0.042(3) Uani 1 d . . 
H9A H 0.0657(3) -0.0943(13) -0.1917(10) 0.062 Uiso 1 calc R . 
H9B H 0.0155(3) -0.1581(13) -0.1173(10) 0.062 Uiso 1 calc R . 
H9C H 0.0671(3) -0.1570(13) -0.0406(10) 0.062 Uiso 1 calc R . 
C10 C 0.0123(3) 0.1723(17) 0.0530(9) 0.052(3) Uani 1 d . . 
H10A H 0.0069(3) 0.3305(17) 0.0773(9) 0.078 Uiso 1 calc R . 
H10B H 0.0319(3) 0.0969(17) 0.1205(9) 0.078 Uiso 1 calc R . 
H10C H -0.0197(3) 0.0958(17) 0.0437(9) 0.078 Uiso 1 calc R . 
C11 C 0.1169(3) 0.2550(15) -0.2954(7) 0.019(2) Uani 1 d . . 
C12 C 0.0984(3) 0.4101(16) -0.3859(7) 0.025(2) Uani 1 d . . 
H12 H 0.0870(3) 0.5546(16) -0.3589(7) 0.030 Uiso 1 calc R . 
C13 C 0.0971(3) 0.3483(18) -0.5165(8) 0.034(3) Uani 1 d . . 
H13 H 0.0839(3) 0.4504(18) -0.5787(8) 0.040 Uiso 1 calc R . 
C14 C 0.1144(3) 0.1449(16) -0.5556(8) 0.030(2) Uani 1 d . . 
H14 H 0.1140(3) 0.1063(16) -0.6452(8) 0.036 Uiso 1 calc R . 
C15 C 0.1329(3) -0.0097(17) -0.4641(8) 0.029(2) Uani 1 d . . 
H15 H 0.1443(3) -0.1542(17) -0.4912(8) 0.035 Uiso 1 calc R . 
C16 C 0.1345(3) 0.0485(16) -0.3372(8) 0.028(2) Uani 1 d . . 
H16 H 0.1480(3) -0.0545(16) -0.2759(8) 0.034 Uiso 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 
P1 0.0335(13) 0.0351(13) 0.0123(11) -0.0016(13) 0.0018(11) -0.0023(13) 
P2 0.0270(11) 0.0351(13) 0.0170(11) -0.0043(13) 0.0031(12) -0.0056(11) 
N 0.032(4) 0.024(4) 0.016(4) -0.002(3) -0.005(3) 0.001(3) 
C1 0.033(5) 0.021(5) 0.008(4) -0.002(4) -0.009(4) 0.008(4) 
C2 0.029(5) 0.029(5) 0.019(4) 0.008(5) 0.003(4) 0.002(4) 
C3 0.025(4) 0.022(4) 0.015(5) -0.004(4) 0.003(4) -0.007(4) 
C4 0.043(6) 0.045(6) 0.038(6) 0.002(5) -0.009(5) -0.014(5) 
C5 0.051(6) 0.057(7) 0.045(6) -0.027(6) -0.002(6) -0.006(6) 
C6 0.056(6) 0.044(6) 0.046(6) 0.008(6) -0.027(6) -0.009(5) 
C7 0.026(5) 0.031(5) 0.027(6) 0.002(5) -0.002(4) -0.006(4) 
C8 0.033(5) 0.040(6) 0.043(7) 0.001(5) -0.003(5) -0.012(5) 
C9 0.035(5) 0.026(5) 0.064(8) 0.015(5) 0.000(5) -0.008(4) 
C10 0.042(6) 0.079(9) 0.036(7) -0.007(6) 0.011(5) -0.024(6) 
C11 0.023(4) 0.025(5) 0.009(5) 0.000(4) 0.000(4) -0.005(4) 
C12 0.031(5) 0.020(5) 0.024(6) -0.008(4) -0.002(4) 0.007(4) 
C13 0.039(6) 0.044(7) 0.019(6) 0.007(5) 0.001(4) -0.012(5) 
C14 0.028(5) 0.051(6) 0.011(5) -0.008(5) 0.002(5) -0.003(5) 
C15 0.037(5) 0.028(6) 0.021(5) -0.009(4) 0.005(4) -0.004(5) 
C16 0.027(5) 0.029(6) 0.028(6) 0.004(5) 0.002(4) -0.003(4) 
  
_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 
P1 C2 1.740(9) . ? 
P1 C1 1.746(8) . ? 
P2 C1 1.697(8) . ? 
P2 N 1.715(6) . ? 
N C2 1.366(10) . ? 
N C11 1.446(10) . ? 
C1 C3 1.542(11) . ? 
C2 C7 1.534(11) . ? 
C3 C5 1.522(11) . ? 
C3 C4 1.530(11) . ? 
C3 C6 1.536(11) . ? 
C7 C9 1.509(11) . ? 
C7 C10 1.518(12) . ? 
C7 C8 1.553(11) . ? 
C11 C16 1.380(12) . ? 
C11 C12 1.399(12) . ? 
C12 C13 1.394(12) . ? 
C13 C14 1.352(12) . ? 
C14 C15 1.406(12) . ? 
C15 C16 1.351(12) . ? 
  
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 
C2 P1 C1 95.8(4) . . ? 
C1 P2 N 95.0(4) . . ? 
C2 N C11 127.6(7) . . ? 
C2 N P2 119.6(5) . . ? 
C11 N P2 112.7(5) . . ? 
C3 C1 P2 122.2(6) . . ? 
C3 C1 P1 121.9(6) . . ? 
P2 C1 P1 115.8(5) . . ? 
N C2 C7 124.4(8) . . ? 
N C2 P1 113.7(6) . . ? 
C7 C2 P1 121.8(6) . . ? 
C5 C3 C4 108.6(7) . . ? 
C5 C3 C6 110.1(7) . . ? 
C4 C3 C6 109.8(7) . . ? 
C5 C3 C1 109.6(6) . . ? 
C4 C3 C1 110.7(6) . . ? 
C6 C3 C1 108.0(7) . . ? 
C9 C7 C10 107.9(7) . . ? 
C9 C7 C2 111.7(7) . . ? 
C10 C7 C2 109.4(7) . . ? 
C9 C7 C8 110.2(7) . . ? 
C10 C7 C8 107.0(7) . . ? 
C2 C7 C8 110.5(7) . . ? 
C16 C11 C12 119.7(7) . . ? 
C16 C11 N 122.4(7) . . ? 
C12 C11 N 117.6(7) . . ? 
C13 C12 C11 118.7(9) . . ? 
C14 C13 C12 120.8(9) . . ? 
C13 C14 C15 120.1(8) . . ? 
C16 C15 C14 119.6(9) . . ? 
C15 C16 C11 121.1(9) . . ? 
  
_refine_diff_density_max    0.276 
_refine_diff_density_min   -0.306 
_refine_diff_density_rms    0.067