# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2001

data_global

_journal_coden_Cambridge      207

_publ_requested_journal       'Perkin Transactions 1'

loop_
_publ_author_name
'Alcock, N.'
'Eldred, Colin'
'Smyth, Donald'
'Tye, Heather'
'Wills, M.'

_publ_contact_author_name     	'Dr M Wills'  
_publ_contact_author_address 
;
Dr M Wills
Department of Chemistry
University of Warwick
Coventry
CV4 7AL
UK
;

_publ_contact_author_email       'M.WILLS@WARWICK.AC.UK'

_publ_section_title
;
Synthesis and Applications to Asymmetric Catalysis of a Series of
Mono and Bi(Diazaphospholidine) Ligands
;

data_dipbor 

_database_code_CSD	169156


_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum 
'C22 H42 B2 N4 P2' 
_chemical_formula_weight     446.16 
_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' 
'B'  'B'   0.0013   0.0007 
'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    P2(1)2(1)2(1)

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

_cell_length_a                    13.347(2) 
_cell_length_b                    13.738(2) 
_cell_length_c                    14.152(2) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      2595.04(13) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     180(2) 
_cell_measurement_reflns_used     7843 
_cell_measurement_theta_min       3
_cell_measurement_theta_max       20 

_exptl_crystal_description        blocks 
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.4
_exptl_crystal_size_mid           0.4
_exptl_crystal_size_min           0.2
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.142 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              968 
_exptl_absorpt_coefficient_mu     0.184 
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.80
_exptl_absorpt_correction_T_max   0.93

_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        ? 
_diffrn_measurement_method        ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             15612 
_diffrn_reflns_av_R_equivalents   0.0433 
_diffrn_reflns_av_sigmaI/netI     0.0634 
_diffrn_reflns_limit_h_min        -17 
_diffrn_reflns_limit_h_max        17 
_diffrn_reflns_limit_k_min        -17 
_diffrn_reflns_limit_k_max        17 
_diffrn_reflns_limit_l_min        -9 
_diffrn_reflns_limit_l_max        19 
_diffrn_reflns_theta_min          2.07 
_diffrn_reflns_theta_max          28.50 
_reflns_number_total              6068 
_reflns_number_observed           4736 
_reflns_observed_criterion        >2sigma(I) 

_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS-96 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-96 (Sheldrick, 1996)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 

_refine_special_details 
; 
Refinement of F^2^ against ALL reflections.  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  
_refine_ls_weighting_details 
'calc w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.1870P] 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    -0.02(8) 
_refine_ls_number_reflns          6068 
_refine_ls_number_parameters      277 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0743 
_refine_ls_R_factor_obs           0.0493 
_refine_ls_wR_factor_all          0.1044 
_refine_ls_wR_factor_obs          0.0941 
_refine_ls_goodness_of_fit_all    1.037 
_refine_ls_goodness_of_fit_obs    1.064 
_refine_ls_restrained_S_all       1.037 
_refine_ls_restrained_S_obs       1.064 
_refine_ls_shift/esd_max          0.849 
_refine_ls_shift/esd_mean         0.019 

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 0.14204(5) 0.07938(4) 0.16233(4) 0.02694(15) Uani 1 d . . 
P2 P 0.33619(5) 0.23075(4) 0.27070(5) 0.02971(16) Uani 1 d . . 
B1 B 0.0957(2) 0.1541(2) 0.0582(2) 0.0355(7) Uani 1 d . . 
H01A H 0.0910 0.1096 -0.0019 0.053 Uiso 1 calc R . 
H01B H 0.1459 0.2114 0.0452 0.053 Uiso 1 calc R . 
H01C H 0.0246 0.1827 0.0737 0.053 Uiso 1 calc R . 
B2 B 0.4346(2) 0.1503(2) 0.3282(3) 0.0461(8) Uani 1 d . . 
H02A H 0.5062 0.1728 0.3067 0.069 Uiso 1 calc R . 
H02B H 0.4231 0.0777 0.3077 0.069 Uiso 1 calc R . 
H02C H 0.4289 0.1558 0.4020 0.069 Uiso 1 calc R . 
N11 N 0.25348(14) 0.02053(13) 0.16244(15) 0.0292(5) Uani 1 d . . 
N12 N 0.06838(15) -0.01856(14) 0.18197(15) 0.0322(5) Uani 1 d . . 
N21 N 0.32732(14) 0.23736(13) 0.15271(14) 0.0286(4) Uani 1 d . . 
N22 N 0.35086(16) 0.35159(14) 0.29210(14) 0.0354(5) Uani 1 d . . 
C1 C 0.2896(2) -0.00592(19) 0.06706(19) 0.0425(7) Uani 1 d . . 
H1A H 0.3600 -0.0258 0.0707 0.064 Uiso 1 calc R . 
H1B H 0.2833 0.0504 0.0250 0.064 Uiso 1 calc R . 
H1C H 0.2493 -0.0599 0.0424 0.064 Uiso 1 calc R . 
C2 C 0.23379(17) -0.06324(16) 0.22665(19) 0.0303(5) Uani 1 d . . 
H2A H 0.2272 -0.0357 0.2918 0.036 Uiso 1 calc R . 
C3 C 0.31222(19) -0.14313(18) 0.2323(2) 0.0376(6) Uani 1 d . . 
H3A H 0.3777 -0.1153 0.2511 0.045 Uiso 1 calc R . 
H3B H 0.3201 -0.1747 0.1698 0.045 Uiso 1 calc R . 
C4 C 0.2773(2) -0.21803(19) 0.3059(2) 0.0425(7) Uani 1 d . . 
H4A H 0.3246 -0.2736 0.3062 0.051 Uiso 1 calc R . 
H4B H 0.2789 -0.1877 0.3693 0.051 Uiso 1 calc R . 
C5 C 0.1714(2) -0.25590(18) 0.2861(2) 0.0422(7) Uani 1 d . . 
H5A H 0.1716 -0.2937 0.2266 0.051 Uiso 1 calc R . 
H5B H 0.1508 -0.3001 0.3378 0.051 Uiso 1 calc R . 
C6 C 0.09559(19) -0.17268(17) 0.2781(2) 0.0359(6) Uani 1 d . . 
H6A H 0.0284 -0.1988 0.2625 0.043 Uiso 1 calc R . 
H6B H 0.0911 -0.1371 0.3388 0.043 Uiso 1 calc R . 
C7 C 0.13103(18) -0.10496(16) 0.20056(18) 0.0300(5) Uani 1 d . . 
H7A H 0.1377 -0.1430 0.1407 0.036 Uiso 1 calc R . 
C8 C -0.0257(2) -0.0355(2) 0.1322(2) 0.0461(8) Uani 1 d . . 
H8A H -0.0679 -0.0794 0.1695 0.069 Uiso 1 calc R . 
H8B H -0.0118 -0.0650 0.0706 0.069 Uiso 1 calc R . 
H8C H -0.0605 0.0266 0.1231 0.069 Uiso 1 calc R . 
C9 C 0.13707(17) 0.14284(15) 0.27636(16) 0.0267(5) Uani 1 d . . 
C10 C 0.04751(19) 0.13063(18) 0.32531(18) 0.0347(6) Uani 1 d . . 
H10A H -0.0027 0.0898 0.2989 0.042 Uiso 1 calc R . 
C11 C 0.0289(2) 0.1758(2) 0.41112(19) 0.0409(7) Uani 1 d . . 
H11A H -0.0335 0.1666 0.4422 0.049 Uiso 1 calc R . 
C12 C 0.1014(2) 0.23408(19) 0.45087(18) 0.0395(7) Uani 1 d . . 
H12A H 0.0905 0.2637 0.5106 0.047 Uiso 1 calc R . 
C13 C 0.1902(2) 0.24898(18) 0.40292(17) 0.0350(6) Uani 1 d . . 
H13A H 0.2394 0.2904 0.4301 0.042 Uiso 1 calc R . 
C14 C 0.21033(18) 0.20499(16) 0.31550(16) 0.0267(5) Uani 1 d . . 
C15 C 0.4182(2) 0.2084(2) 0.10044(19) 0.0416(7) Uani 1 d . . 
H15A H 0.4025 0.2027 0.0330 0.062 Uiso 1 calc R . 
H15B H 0.4421 0.1455 0.1241 0.062 Uiso 1 calc R . 
H15C H 0.4705 0.2576 0.1095 0.062 Uiso 1 calc R . 
C16 C 0.29082(18) 0.33848(17) 0.13452(16) 0.0277(5) Uani 1 d . . 
H16A H 0.2187 0.3407 0.1537 0.033 Uiso 1 calc R . 
C17 C 0.2967(2) 0.37561(18) 0.03450(18) 0.0365(6) Uani 1 d . . 
H17A H 0.2591 0.3319 -0.0084 0.044 Uiso 1 calc R . 
H17B H 0.3674 0.3779 0.0133 0.044 Uiso 1 calc R . 
C18 C 0.2508(2) 0.47846(19) 0.0327(2) 0.0471(8) Uani 1 d . . 
H18A H 0.2583 0.5062 -0.0315 0.057 Uiso 1 calc R . 
H18B H 0.1783 0.4741 0.0468 0.057 Uiso 1 calc R . 
C19 C 0.3009(2) 0.5463(2) 0.1044(2) 0.0474(8) Uani 1 d . . 
H19A H 0.3712 0.5579 0.0851 0.057 Uiso 1 calc R . 
H19B H 0.2658 0.6098 0.1042 0.057 Uiso 1 calc R . 
C20 C 0.2994(2) 0.50447(19) 0.20420(19) 0.0417(7) Uani 1 d . . 
H20A H 0.3366 0.5478 0.2477 0.050 Uiso 1 calc R . 
H20B H 0.2295 0.4989 0.2270 0.050 Uiso 1 calc R . 
C21 C 0.34812(18) 0.40497(16) 0.20174(16) 0.0303(5) Uani 1 d . . 
H21A H 0.4182 0.4123 0.1779 0.036 Uiso 1 calc R . 
C22 C 0.4217(2) 0.3882(2) 0.3621(2) 0.0468(7) Uani 1 d . . 
H22A H 0.4044 0.4555 0.3784 0.070 Uiso 1 calc R . 
H22B H 0.4896 0.3863 0.3359 0.070 Uiso 1 calc R . 
H22C H 0.4186 0.3476 0.4189 0.070 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 0.0290(3) 0.0257(3) 0.0262(3) 0.0012(3) 0.0001(3) 0.0009(3) 
P2 0.0310(3) 0.0304(3) 0.0277(3) 0.0034(3) -0.0018(3) 0.0008(3) 
B1 0.0430(18) 0.0329(15) 0.0305(16) 0.0048(14) -0.0071(14) 0.0021(14) 
B2 0.0377(18) 0.0494(19) 0.051(2) 0.0117(18) -0.0122(16) 0.0076(15) 
N11 0.0320(10) 0.0253(10) 0.0304(11) 0.0027(10) 0.0065(10) 0.0010(9) 
N12 0.0285(11) 0.0273(10) 0.0407(14) 0.0009(10) -0.0018(9) -0.0023(8) 
N21 0.0329(11) 0.0272(10) 0.0257(10) 0.0005(9) 0.0039(9) 0.0037(9) 
N22 0.0438(13) 0.0343(11) 0.0282(11) 0.0003(9) -0.0076(11) -0.0068(10) 
C1 0.0486(16) 0.0396(15) 0.0394(16) 0.0014(14) 0.0143(14) 0.0061(13) 
C2 0.0314(12) 0.0277(12) 0.0317(13) 0.0029(11) 0.0034(11) 0.0031(10) 
C3 0.0338(14) 0.0310(13) 0.0480(16) 0.0006(13) -0.0006(13) 0.0033(11) 
C4 0.0478(17) 0.0309(14) 0.0489(17) 0.0054(13) -0.0086(13) 0.0061(12) 
C5 0.0491(16) 0.0316(13) 0.0459(16) 0.0079(13) -0.0013(14) 0.0014(12) 
C6 0.0379(14) 0.0312(13) 0.0386(15) 0.0058(13) 0.0010(13) -0.0054(11) 
C7 0.0321(13) 0.0259(12) 0.0321(13) -0.0027(10) 0.0008(11) 0.0016(10) 
C8 0.0366(15) 0.0380(15) 0.064(2) 0.0072(14) -0.0109(15) -0.0013(13) 
C9 0.0287(12) 0.0249(11) 0.0266(12) 0.0053(10) 0.0007(11) 0.0046(10) 
C10 0.0328(14) 0.0387(14) 0.0327(15) 0.0011(12) 0.0039(12) 0.0012(11) 
C11 0.0406(16) 0.0487(17) 0.0334(15) 0.0041(13) 0.0128(13) 0.0060(14) 
C12 0.0553(18) 0.0372(14) 0.0259(14) 0.0028(12) 0.0097(13) 0.0101(13) 
C13 0.0471(16) 0.0331(14) 0.0249(13) 0.0011(11) -0.0006(12) 0.0034(12) 
C14 0.0338(12) 0.0223(11) 0.0240(13) 0.0048(10) 0.0006(10) 0.0032(10) 
C15 0.0456(16) 0.0403(15) 0.0389(16) -0.0020(13) 0.0121(13) 0.0035(13) 
C16 0.0288(12) 0.0288(13) 0.0254(13) 0.0019(10) 0.0027(10) -0.0017(10) 
C17 0.0444(15) 0.0377(15) 0.0274(14) 0.0056(12) -0.0007(13) -0.0067(12) 
C18 0.0517(17) 0.0479(18) 0.0418(18) 0.0183(15) 0.0021(14) 0.0028(15) 
C19 0.0607(19) 0.0282(14) 0.0533(19) 0.0090(13) 0.0087(16) 0.0028(13) 
C20 0.0533(17) 0.0303(13) 0.0416(16) -0.0018(13) 0.0081(14) -0.0015(12) 
C21 0.0325(13) 0.0301(12) 0.0283(12) 0.0006(10) 0.0022(11) -0.0060(11) 
C22 0.0468(17) 0.0537(17) 0.0398(17) -0.0092(14) -0.0107(13) -0.0064(14) 

_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 N12 1.689(2) . ? 
P1 N11 1.693(2) . ? 
P1 C9 1.835(2) . ? 
P1 B1 1.900(3) . ? 
P2 N21 1.676(2) . ? 
P2 N22 1.699(2) . ? 
P2 C14 1.830(2) . ? 
P2 B2 1.900(3) . ? 
N11 C1 1.478(3) . ? 
N11 C2 1.490(3) . ? 
N12 C8 1.458(3) . ? 
N12 C7 1.476(3) . ? 
N21 C15 1.476(3) . ? 
N21 C16 1.494(3) . ? 
N22 C22 1.459(3) . ? 
N22 C21 1.475(3) . ? 
C2 C3 1.519(3) . ? 
C2 C7 1.532(3) . ? 
C3 C4 1.536(4) . ? 
C4 C5 1.533(4) . ? 
C5 C6 1.531(3) . ? 
C6 C7 1.514(3) . ? 
C9 C10 1.392(3) . ? 
C9 C14 1.411(3) . ? 
C10 C11 1.386(4) . ? 
C11 C12 1.377(4) . ? 
C12 C13 1.381(4) . ? 
C13 C14 1.403(3) . ? 
C16 C17 1.507(3) . ? 
C16 C21 1.525(3) . ? 
C17 C18 1.540(4) . ? 
C18 C19 1.532(4) . ? 
C19 C20 1.525(4) . ? 
C20 C21 1.514(3) . ? 

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 
N12 P1 N11 97.51(10) . . ? 
N12 P1 C9 102.27(11) . . ? 
N11 P1 C9 104.93(10) . . ? 
N12 P1 B1 111.64(12) . . ? 
N11 P1 B1 123.02(13) . . ? 
C9 P1 B1 114.44(12) . . ? 
N21 P2 N22 97.63(10) . . ? 
N21 P2 C14 106.90(10) . . ? 
N22 P2 C14 103.48(11) . . ? 
N21 P2 B2 120.45(14) . . ? 
N22 P2 B2 114.37(13) . . ? 
C14 P2 B2 111.95(13) . . ? 
C1 N11 C2 115.12(18) . . ? 
C1 N11 P1 113.74(17) . . ? 
C2 N11 P1 102.39(14) . . ? 
C8 N12 C7 116.48(19) . . ? 
C8 N12 P1 123.26(18) . . ? 
C7 N12 P1 109.89(15) . . ? 
C15 N21 C16 115.63(19) . . ? 
C15 N21 P2 115.25(17) . . ? 
C16 N21 P2 104.18(14) . . ? 
C22 N22 C21 115.7(2) . . ? 
C22 N22 P2 122.21(18) . . ? 
C21 N22 P2 109.18(15) . . ? 
N11 C2 C3 117.9(2) . . ? 
N11 C2 C7 107.46(19) . . ? 
C3 C2 C7 111.06(19) . . ? 
C2 C3 C4 108.1(2) . . ? 
C5 C4 C3 112.6(2) . . ? 
C6 C5 C4 111.7(2) . . ? 
C7 C6 C5 107.9(2) . . ? 
N12 C7 C6 116.5(2) . . ? 
N12 C7 C2 104.44(18) . . ? 
C6 C7 C2 109.6(2) . . ? 
C10 C9 C14 118.2(2) . . ? 
C10 C9 P1 114.29(18) . . ? 
C14 C9 P1 127.40(18) . . ? 
C11 C10 C9 122.4(2) . . ? 
C12 C11 C10 119.5(3) . . ? 
C11 C12 C13 119.3(2) . . ? 
C12 C13 C14 122.3(3) . . ? 
C13 C14 C9 118.3(2) . . ? 
C13 C14 P2 113.44(18) . . ? 
C9 C14 P2 128.10(18) . . ? 
N21 C16 C17 117.4(2) . . ? 
N21 C16 C21 106.62(18) . . ? 
C17 C16 C21 110.93(19) . . ? 
C16 C17 C18 107.8(2) . . ? 
C19 C18 C17 112.0(2) . . ? 
C20 C19 C18 112.2(2) . . ? 
C21 C20 C19 108.3(2) . . ? 
N22 C21 C20 116.1(2) . . ? 
N22 C21 C16 104.80(17) . . ? 
C20 C21 C16 109.9(2) . . ? 

_refine_diff_density_max    0.261 
_refine_diff_density_min   -0.267 
_refine_diff_density_rms    0.048 

data_typhosa 

_database_code_CSD	169157


_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C15 H26 B N2 O P' 
_chemical_formula_weight          292.16 
_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' 
'B'  'B'   0.0013   0.0007 
'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' 
'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    P2(1)2(1)2(1)

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

_cell_length_a                    8.300(4) 
_cell_length_b                    13.789(5) 
_cell_length_c                    14.553(5) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      1665.6(11) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     200(2) 
_cell_measurement_reflns_used     2780 
_cell_measurement_theta_min       6 
_cell_measurement_theta_max       20 

_exptl_crystal_description        blocks
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.2
_exptl_crystal_size_mid           0.2
_exptl_crystal_size_min           0.16
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.165 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              632 
_exptl_absorpt_coefficient_mu     0.163 
_exptl_absorpt_correction_type    psi-scan
_exptl_absorpt_correction_T_min   0.61
_exptl_absorpt_correction_T_max   0.68

_exptl_special_details 
; 
? 
; 

_diffrn_ambient_temperature       200(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        ? 
_diffrn_measurement_method        ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             7586 
_diffrn_reflns_av_R_equivalents   0.0852 
_diffrn_reflns_av_sigmaI/netI     0.1013 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        18 
_diffrn_reflns_limit_l_min        -19 
_diffrn_reflns_limit_l_max        19 
_diffrn_reflns_theta_min          2.03 
_diffrn_reflns_theta_max          24.00 
_reflns_number_total              2605 
_reflns_number_observed           1846 
_reflns_observed_criterion        >2sigma(I) 

_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS-96 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-96 (Sheldrick, 1996)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 

_refine_special_details 
; 
Refinement of F^2^ against ALL reflections.  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  
_refine_ls_weighting_details 
'calc w=1/[\s^2^(Fo^2^)+(0.0220P)^2^+0.7000P] 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     ? 
_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    0.23(19) 
_refine_ls_number_reflns          2605 
_refine_ls_number_parameters      193 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1065 
_refine_ls_R_factor_obs           0.0637 
_refine_ls_wR_factor_all          0.1124 
_refine_ls_wR_factor_obs          0.0973 
_refine_ls_goodness_of_fit_all    1.068 
_refine_ls_goodness_of_fit_obs    1.114 
_refine_ls_restrained_S_all       1.068 
_refine_ls_restrained_S_obs       1.114 
_refine_ls_shift/esd_max          0.001 
_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 0.76835(13) 0.93023(8) 0.77864(8) 0.0333(3) Uani 1 d . . 
C1 C 0.7629(5) 0.8171(3) 0.8432(3) 0.0318(10) Uani 1 d . . 
C2 C 0.9030(5) 0.7813(3) 0.8835(3) 0.0410(13) Uani 1 d . . 
H2A H 0.9997 0.8179 0.8795 0.049 Uiso 1 calc R . 
C3 C 0.9035(7) 0.6930(3) 0.9295(3) 0.0489(14) Uani 1 d . . 
H3A H 0.9997 0.6697 0.9572 0.059 Uiso 1 calc R . 
C4 C 0.7645(7) 0.6398(3) 0.9345(3) 0.0522(14) Uani 1 d . . 
H4A H 0.7655 0.5791 0.9655 0.063 Uiso 1 calc R . 
C5 C 0.6238(6) 0.6723(3) 0.8958(3) 0.0473(13) Uani 1 d . . 
H5A H 0.5286 0.6341 0.8984 0.057 Uiso 1 calc R . 
C6 C 0.6230(6) 0.7630(3) 0.8522(3) 0.0376(12) Uani 1 d . . 
O7 O 0.4862(4) 0.8030(2) 0.8174(2) 0.0568(10) Uani 1 d . . 
C8 C 0.3464(6) 0.7437(4) 0.8077(5) 0.088(2) Uani 1 d . . 
H8A H 0.2599 0.7815 0.7791 0.131 Uiso 1 calc R . 
H8B H 0.3114 0.7213 0.8684 0.131 Uiso 1 calc R . 
H8C H 0.3718 0.6877 0.7689 0.131 Uiso 1 calc R . 
N9 N 0.9678(4) 0.9482(2) 0.7614(2) 0.0344(9) Uani 1 d . . 
C10 C 1.0343(5) 0.9270(4) 0.6708(3) 0.0546(13) Uani 1 d . . 
H10A H 1.1522 0.9277 0.6740 0.082 Uiso 1 calc R . 
H10B H 0.9977 0.9761 0.6269 0.082 Uiso 1 calc R . 
H10C H 0.9977 0.8628 0.6507 0.082 Uiso 1 calc R . 
C11 C 1.0140(5) 1.0413(3) 0.8029(3) 0.0339(11) Uani 1 d . . 
H11A H 0.9872 1.0944 0.7587 0.041 Uiso 1 calc R . 
C12 C 1.1904(5) 1.0511(3) 0.8307(3) 0.0435(12) Uani 1 d . . 
H12A H 1.2606 1.0453 0.7760 0.052 Uiso 1 calc R . 
H12B H 1.2198 0.9992 0.8746 0.052 Uiso 1 calc R . 
C13 C 1.2124(5) 1.1506(3) 0.8754(4) 0.0525(14) Uani 1 d . . 
H13A H 1.3240 1.1559 0.8990 0.063 Uiso 1 calc R . 
H13B H 1.1973 1.2015 0.8282 0.063 Uiso 1 calc R . 
C14 C 1.0955(6) 1.1684(4) 0.9539(3) 0.0511(15) Uani 1 d . . 
H14A H 1.1226 1.1246 1.0055 0.061 Uiso 1 calc R . 
H14B H 1.1083 1.2359 0.9758 0.061 Uiso 1 calc R . 
C15 C 0.9212(5) 1.1522(3) 0.9265(3) 0.0426(13) Uani 1 d . . 
H15A H 0.8877 1.2013 0.8807 0.051 Uiso 1 calc R . 
H15B H 0.8504 1.1581 0.9809 0.051 Uiso 1 calc R . 
C16 C 0.9074(5) 1.0511(3) 0.8857(3) 0.0328(11) Uani 1 d . . 
H16A H 0.9420 1.0027 0.9329 0.039 Uiso 1 calc R . 
N17 N 0.7468(4) 1.0237(2) 0.8514(2) 0.0330(8) Uani 1 d . . 
C18 C 0.6181(5) 1.0177(3) 0.9200(3) 0.0436(13) Uani 1 d . . 
H18A H 0.5960 1.0825 0.9446 0.065 Uiso 1 calc R . 
H18B H 0.6518 0.9747 0.9700 0.065 Uiso 1 calc R . 
H18C H 0.5204 0.9918 0.8912 0.065 Uiso 1 calc R . 
B19 B 0.6358(8) 0.9386(5) 0.6726(4) 0.0497(15) Uani 1 d . . 
H19A H 0.6961(47) 1.0026(32) 0.6349(31) 0.074 Uiso 1 d . . 
H19B H 0.6441(52) 0.8662(32) 0.6423(31) 0.074 Uiso 1 d . . 
H19C H 0.5069(53) 0.9533(31) 0.6971(31) 0.074 Uiso 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 
P1 0.0377(7) 0.0299(6) 0.0324(6) -0.0002(6) -0.0007(6) 0.0008(6) 
C1 0.033(3) 0.028(2) 0.034(3) -0.0048(19) 0.008(2) 0.004(2) 
C2 0.039(3) 0.038(3) 0.046(3) -0.005(3) -0.003(3) -0.001(2) 
C3 0.062(4) 0.037(3) 0.048(3) 0.007(3) -0.011(3) 0.003(3) 
C4 0.081(4) 0.035(3) 0.041(3) 0.004(2) 0.008(3) -0.003(3) 
C5 0.050(3) 0.037(3) 0.055(4) 0.002(3) 0.005(3) -0.012(3) 
C6 0.040(3) 0.032(3) 0.040(3) -0.006(2) 0.001(3) -0.002(2) 
O7 0.039(2) 0.048(2) 0.084(3) 0.0107(19) -0.0097(19) -0.0076(18) 
C8 0.048(3) 0.077(4) 0.138(6) 0.009(4) -0.024(4) -0.025(3) 
N9 0.041(2) 0.029(2) 0.033(2) 0.0004(17) 0.0113(17) -0.0018(18) 
C10 0.066(3) 0.047(3) 0.051(3) -0.009(3) 0.019(3) 0.010(3) 
C11 0.039(3) 0.030(3) 0.033(3) 0.004(2) 0.003(2) 0.002(2) 
C12 0.040(3) 0.042(3) 0.049(3) 0.007(2) 0.003(2) -0.005(2) 
C13 0.039(3) 0.045(3) 0.073(4) 0.007(3) -0.010(3) -0.011(3) 
C14 0.060(4) 0.042(3) 0.050(4) -0.002(3) -0.020(3) -0.006(3) 
C15 0.051(3) 0.039(3) 0.037(3) 0.000(2) 0.001(3) 0.003(3) 
C16 0.038(3) 0.028(3) 0.032(3) 0.008(2) -0.005(2) 0.000(2) 
N17 0.033(2) 0.0369(19) 0.029(2) -0.0021(15) 0.006(2) 0.0001(19) 
C18 0.040(3) 0.045(3) 0.046(3) -0.012(2) 0.006(3) -0.007(2) 
B19 0.062(4) 0.048(4) 0.039(3) 0.003(3) -0.013(3) 0.013(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 N17 1.6777(32) . ? 
P1 N9 1.6926(34) . ? 
P1 C1 1.8224(40) . ? 
P1 B19 1.8984(55) . ? 
C1 C6 1.3858(55) . ? 
C1 C2 1.3926(58) . ? 
C2 C3 1.3886(57) . ? 
C3 C4 1.3695(62) . ? 
C4 C5 1.3726(61) . ? 
C5 C6 1.4022(58) . ? 
C6 O7 1.3600(49) . ? 
O7 C8 1.4260(49) . ? 
N9 C10 1.4586(49) . ? 
N9 C11 1.4691(47) . ? 
C11 C16 1.5013(53) . ? 
C11 C12 1.5252(54) . ? 
C12 C13 1.5303(56) . ? 
C13 C14 1.5185(63) . ? 
C14 C15 1.5171(60) . ? 
C15 C16 1.5189(56) . ? 
C16 N17 1.4731(51) . ? 
N17 C18 1.4645(49) . ? 
B19 H19A 1.1541(433) . ? 
B19 H19B 1.0936(425) . ? 
B19 H19C 1.1460(436) . ? 

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 
N17 P1 N9 94.91(17) . . ? 
N17 P1 C1 109.27(17) . . ? 
N9 P1 C1 103.07(19) . . ? 
N17 P1 B19 113.9(2) . . ? 
N9 P1 B19 115.9(2) . . ? 
C1 P1 B19 117.2(3) . . ? 
C6 C1 C2 118.0(4) . . ? 
C6 C1 P1 122.0(4) . . ? 
C2 C1 P1 120.0(3) . . ? 
C3 C2 C1 121.1(4) . . ? 
C4 C3 C2 119.5(5) . . ? 
C3 C4 C5 121.3(4) . . ? 
C4 C5 C6 118.8(4) . . ? 
O7 C6 C1 116.5(4) . . ? 
O7 C6 C5 122.3(4) . . ? 
C1 C6 C5 121.2(5) . . ? 
C6 O7 C8 118.9(4) . . ? 
O7 C8 H8C 109.5(3) . . ? 
C10 N9 C11 116.6(4) . . ? 
C10 N9 P1 118.3(3) . . ? 
C11 N9 P1 108.8(2) . . ? 
N9 C11 C16 104.8(3) . . ? 
N9 C11 C12 115.9(3) . . ? 
C16 C11 C12 110.1(3) . . ? 
C11 C12 C13 107.9(3) . . ? 
C14 C13 C12 112.9(4) . . ? 
C15 C14 C13 112.8(4) . . ? 
C14 C15 C16 108.0(4) . . ? 
N17 C16 C11 103.7(3) . . ? 
N17 C16 C15 115.9(3) . . ? 
C11 C16 C15 110.6(3) . . ? 
C18 N17 C16 116.3(3) . . ? 
C18 N17 P1 117.6(3) . . ? 
C16 N17 P1 108.3(3) . . ? 

_refine_diff_density_max    0.207 
_refine_diff_density_min   -0.281 
_refine_diff_density_rms    0.060