# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_z1
_database_code_depnum_ccdc_archive 'CCDC 1402338'
_audit_update_record             
;
2015-05-22 deposited with the CCDC.
2015-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            dippy
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H24 B2 N2 O2'
_chemical_formula_weight         514.17

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   11.169(2)
_cell_length_b                   16.752(3)
_cell_length_c                   14.317(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.57(3)
_cell_angle_gamma                90.00
_cell_volume                     2567.5(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24493
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_av_sigmaI/netI    0.0670
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5844
_reflns_number_gt                3240
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0575P)²+0.1323P] where P=(Fo²+2Fc²)/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         5844
_refine_ls_number_parameters     457
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1189
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1383
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.62312(14) 0.25374(9) 0.66094(11) 0.0456(4) Uani 1 1 d . . .
N2 N 1.09723(16) 0.30752(10) 0.60012(12) 0.0373(4) Uani 1 1 d . . .
O2 O 1.07041(14) 0.36679(9) 0.75430(11) 0.0515(4) Uani 1 1 d . . .
N1 N 0.75159(17) 0.32353(10) 0.80969(13) 0.0408(4) Uani 1 1 d . . .
C23 C 0.88246(19) 0.36810(11) 0.60879(15) 0.0358(5) Uani 1 1 d . . .
C17 C 1.26818(19) 0.37000(12) 0.72013(16) 0.0396(5) Uani 1 1 d . . .
C16 C 1.21858(19) 0.32927(11) 0.62653(16) 0.0375(5) Uani 1 1 d . . .
C34 C 0.97289(19) 0.23123(12) 0.70225(14) 0.0357(5) Uani 1 1 d . . .
C33 C 1.0621(2) 0.16998(14) 0.71872(17) 0.0475(6) Uani 1 1 d . . .
C5 C 0.6816(2) 0.29088(13) 0.86336(17) 0.0451(6) Uani 1 1 d . . .
C30 C 0.8428(2) 0.14333(12) 0.76446(17) 0.0451(6) Uani 1 1 d . . .
C27 C 0.6699(2) 0.40914(13) 0.58973(18) 0.0485(6) Uani 1 1 d . . .
C6 C 0.5893(2) 0.23011(13) 0.81683(18) 0.0477(6) Uani 1 1 d . . .
C28 C 0.76914(19) 0.35732(11) 0.63253(15) 0.0365(5) Uani 1 1 d . . .
C29 C 0.85875(19) 0.21812(11) 0.72414(14) 0.0349(5) Uani 1 1 d . . .
C11 C 0.5635(2) 0.21465(12) 0.71692(18) 0.0447(5) Uani 1 1 d . . .
C22 C 1.1908(2) 0.38629(12) 0.77929(16) 0.0413(5) Uani 1 1 d . . .
C12 C 1.0473(2) 0.27035(14) 0.51383(16) 0.0479(6) Uani 1 1 d . . .
C14 C 1.2385(3) 0.27387(16) 0.4765(2) 0.0571(7) Uani 1 1 d . . .
B2 B 1.0040(2) 0.31830(14) 0.66655(17) 0.0361(5) Uani 1 1 d . . .
C24 C 0.8879(2) 0.42679(13) 0.54063(18) 0.0468(6) Uani 1 1 d . . .
C15 C 1.2905(2) 0.31199(14) 0.5634(2) 0.0516(6) Uani 1 1 d . . .
C31 C 0.9332(2) 0.08418(13) 0.78187(18) 0.0516(6) Uani 1 1 d . . .
C4 C 0.6988(3) 0.31891(17) 0.95892(19) 0.0582(7) Uani 1 1 d . . .
B1 B 0.7513(2) 0.28599(14) 0.70302(17) 0.0368(5) Uani 1 1 d . . .
C25 C 0.7874(2) 0.47494(13) 0.4976(2) 0.0544(7) Uani 1 1 d . . .
C21 C 1.2392(3) 0.42586(15) 0.8683(2) 0.0582(7) Uani 1 1 d . . .
C13 C 1.1153(3) 0.25222(16) 0.45099(19) 0.0546(6) Uani 1 1 d . . .
C26 C 0.6784(3) 0.46699(14) 0.5231(2) 0.0556(7) Uani 1 1 d . . .
C1 C 0.8324(2) 0.38299(14) 0.84725(18) 0.0523(6) Uani 1 1 d . . .
C32 C 1.0429(3) 0.09696(14) 0.75851(19) 0.0545(7) Uani 1 1 d . . .
C10 C 0.4711(2) 0.16017(15) 0.6713(2) 0.0588(7) Uani 1 1 d . . .
C3 C 0.7827(3) 0.37801(17) 0.9974(2) 0.0645(8) Uani 1 1 d . . .
C18 C 1.3928(2) 0.39654(16) 0.7514(2) 0.0633(7) Uani 1 1 d . . .
C7 C 0.5214(3) 0.18790(17) 0.8696(3) 0.0699(8) Uani 1 1 d . . .
C20 C 1.3612(3) 0.45028(16) 0.8970(2) 0.0703(8) Uani 1 1 d . . .
C19 C 1.4380(3) 0.43630(17) 0.8383(3) 0.0769(9) Uani 1 1 d . . .
C2 C 0.8488(3) 0.41128(18) 0.9400(2) 0.0668(8) Uani 1 1 d . . .
C8 C 0.4312(3) 0.13421(18) 0.8254(3) 0.0839(11) Uani 1 1 d . . .
C9 C 0.4057(3) 0.12044(17) 0.7267(3) 0.0770(10) Uani 1 1 d . . .
H1 H 0.958(2) 0.2585(13) 0.5026(17) 0.059(7) Uiso 1 1 d . . .
H2 H 1.112(2) 0.0567(14) 0.7749(18) 0.064(7) Uiso 1 1 d . . .
H3 H 0.961(2) 0.4340(12) 0.5215(16) 0.043(6) Uiso 1 1 d . . .
H4 H 0.602(2) 0.5002(14) 0.4915(19) 0.071(8) Uiso 1 1 d . . .
H5 H 0.920(2) 0.0315(14) 0.8118(18) 0.063(7) Uiso 1 1 d . . .
H6 H 0.886(2) 0.4049(13) 0.8038(18) 0.063(7) Uiso 1 1 d . . .
H7 H 1.074(2) 0.2229(14) 0.3903(19) 0.062(7) Uiso 1 1 d . . .
H8 H 0.586(2) 0.4046(13) 0.6068(17) 0.059(7) Uiso 1 1 d . . .
H9 H 0.764(2) 0.1326(13) 0.7794(17) 0.059(7) Uiso 1 1 d . . .
H10 H 0.790(2) 0.5138(13) 0.4455(18) 0.059(7) Uiso 1 1 d . . .
H11 H 1.292(2) 0.2604(15) 0.4337(19) 0.073(8) Uiso 1 1 d . . .
H12 H 0.652(2) 0.2933(14) 0.9920(19) 0.059(7) Uiso 1 1 d . . .
H13 H 1.452(3) 0.3838(15) 0.713(2) 0.079(9) Uiso 1 1 d . . .
H14 H 1.180(2) 0.4343(14) 0.9069(18) 0.061(8) Uiso 1 1 d . . .
H15 H 0.346(3) 0.0856(16) 0.689(2) 0.072(9) Uiso 1 1 d . . .
H16 H 0.452(2) 0.1506(13) 0.598(2) 0.062(8) Uiso 1 1 d . . .
H17 H 1.145(3) 0.1805(15) 0.703(2) 0.076(8) Uiso 1 1 d . . .
H18 H 0.913(3) 0.4548(18) 0.964(2) 0.095(10) Uiso 1 1 d . . .
H19 H 1.381(3) 0.3273(14) 0.5840(19) 0.071(8) Uiso 1 1 d . . .
H20 H 1.527(3) 0.4542(18) 0.856(2) 0.106(11) Uiso 1 1 d . . .
H21 H 0.797(3) 0.3957(16) 1.069(2) 0.083(9) Uiso 1 1 d . . .
H22 H 1.392(3) 0.4779(16) 0.962(2) 0.081(9) Uiso 1 1 d . . .
H23 H 0.541(3) 0.2019(18) 0.944(3) 0.101(11) Uiso 1 1 d . . .
H24 H 0.383(3) 0.101(2) 0.861(3) 0.119(12) Uiso 1 1 d . . .


_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 C11 1.349(2) . ?
O1 B1 1.487(3) . ?
N2 C16 1.349(3) . ?
N2 C12 1.354(3) . ?
N2 B2 1.608(3) . ?
O2 C22 1.330(2) . ?
O2 B2 1.502(3) . ?
N1 C1 1.349(3) . ?
N1 C5 1.358(3) . ?
N1 B1 1.651(3) . ?
C23 C24 1.399(3) . ?
C23 C28 1.412(3) . ?
C23 B2 1.607(3) . ?
C17 C22 1.399(3) . ?
C17 C18 1.407(3) . ?
C17 C16 1.465(3) . ?
C16 C15 1.399(3) . ?
C34 C33 1.403(3) . ?
C34 C29 1.414(3) . ?
C34 B2 1.616(3) . ?
C33 C32 1.392(3) . ?
C5 C4 1.407(3) . ?
C5 C6 1.467(3) . ?
C30 C31 1.386(3) . ?
C30 C29 1.412(3) . ?
C27 C26 1.382(3) . ?
C27 C28 1.403(3) . ?
C6 C11 1.400(3) . ?
C6 C7 1.405(3) . ?
C28 B1 1.613(3) . ?
C29 B1 1.618(3) . ?
C11 C10 1.393(3) . ?
C22 C21 1.401(3) . ?
C12 C13 1.366(3) . ?
C14 C13 1.369(4) . ?
C14 C15 1.372(4) . ?
C24 C25 1.377(3) . ?
C31 C32 1.375(3) . ?
C4 C3 1.366(4) . ?
C25 C26 1.372(3) . ?
C21 C20 1.369(4) . ?
C1 C2 1.373(3) . ?
C10 C9 1.391(4) . ?
C3 C2 1.370(4) . ?
C18 C19 1.375(4) . ?
C7 C8 1.364(5) . ?
C20 C19 1.380(4) . ?
C8 C9 1.379(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
C11 O1 B1 121.14(17) . . ?
C16 N2 C12 119.96(19) . . ?
C16 N2 B2 124.90(18) . . ?
C12 N2 B2 115.07(18) . . ?
C22 O2 B2 125.33(17) . . ?
C1 N1 C5 120.0(2) . . ?
C1 N1 B1 118.34(17) . . ?
C5 N1 B1 121.38(18) . . ?
C24 C23 C28 118.5(2) . . ?
C24 C23 B2 121.72(19) . . ?
C28 C23 B2 119.53(17) . . ?
C22 C17 C18 118.1(2) . . ?
C22 C17 C16 120.48(19) . . ?
C18 C17 C16 121.3(2) . . ?
N2 C16 C15 118.6(2) . . ?
N2 C16 C17 118.02(19) . . ?
C15 C16 C17 123.4(2) . . ?
C33 C34 C29 119.43(19) . . ?
C33 C34 B2 120.48(19) . . ?
C29 C34 B2 119.93(17) . . ?
C32 C33 C34 121.8(2) . . ?
N1 C5 C4 118.4(2) . . ?
N1 C5 C6 117.8(2) . . ?
C4 C5 C6 123.8(2) . . ?
C31 C30 C29 122.6(2) . . ?
C26 C27 C28 122.3(2) . . ?
C11 C6 C7 118.1(3) . . ?
C11 C6 C5 120.39(19) . . ?
C7 C6 C5 121.5(3) . . ?
C27 C28 C23 117.76(18) . . ?
C27 C28 B1 120.56(19) . . ?
C23 C28 B1 121.63(18) . . ?
C30 C29 C34 117.06(19) . . ?
C30 C29 B1 121.80(19) . . ?
C34 C29 B1 121.13(17) . . ?
O1 C11 C10 117.7(2) . . ?
O1 C11 C6 121.6(2) . . ?
C10 C11 C6 120.6(2) . . ?
O2 C22 C17 122.8(2) . . ?
O2 C22 C21 117.4(2) . . ?
C17 C22 C21 119.9(2) . . ?
N2 C12 C13 122.8(2) . . ?
C13 C14 C15 119.9(2) . . ?
O2 B2 C23 107.03(17) . . ?
O2 B2 N2 107.85(17) . . ?
C23 B2 N2 110.39(17) . . ?
O2 B2 C34 108.85(17) . . ?
C23 B2 C34 113.92(17) . . ?
N2 B2 C34 108.63(16) . . ?
C25 C24 C23 122.1(2) . . ?
C14 C15 C16 120.7(2) . . ?
C32 C31 C30 119.9(2) . . ?
C3 C4 C5 121.4(3) . . ?
O1 B1 C28 106.99(18) . . ?
O1 B1 C29 113.41(17) . . ?
C28 B1 C29 114.85(17) . . ?
O1 B1 N1 105.11(16) . . ?
C28 B1 N1 109.19(16) . . ?
C29 B1 N1 106.81(17) . . ?
C26 C25 C24 119.7(2) . . ?
C20 C21 C22 120.5(3) . . ?
C12 C13 C14 118.1(3) . . ?
C25 C26 C27 119.5(2) . . ?
N1 C1 C2 122.0(3) . . ?
C31 C32 C33 119.2(2) . . ?
C9 C10 C11 119.1(3) . . ?
C4 C3 C2 118.6(3) . . ?
C19 C18 C17 121.0(3) . . ?
C8 C7 C6 121.5(3) . . ?
C21 C20 C19 120.3(3) . . ?
C18 C19 C20 120.1(3) . . ?
C3 C2 C1 119.6(3) . . ?
C7 C8 C9 119.7(3) . . ?
C8 C9 C10 121.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.040
_exptl_crystal_recrystallization_method Sublimation
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_z1
_database_code_depnum_ccdc_archive 'CCDC 1402340'
_audit_update_record             
;
2015-05-22 deposited with the CCDC.
2015-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            dibm
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H34 B2 N4 O2'
_chemical_formula_weight         744.43

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'

_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                   23.440(5)
_cell_length_b                   9.4816(19)
_cell_length_c                   18.355(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.48(3)
_cell_angle_gamma                90.00
_cell_volume                     3821.6(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.598
_exptl_crystal_size_mid          0.433
_exptl_crystal_size_min          0.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1552
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17271
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4341
_reflns_number_gt                2670
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1056P)²+0.0000P] where P=(Fo²+2Fc²)/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         4341
_refine_ls_number_parameters     330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1722
_refine_ls_wR_factor_gt          0.1445
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_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 0.09641(6) 1.11227(14) 0.11781(7) 0.0573(4) Uani 1 1 d . . .
N1 N 0.07173(6) 0.86880(16) 0.14290(8) 0.0450(4) Uani 1 1 d . . .
C14 C 0.15396(7) 0.99410(19) 0.23817(9) 0.0416(4) Uani 1 1 d . . .
C13 C 0.11485(8) 0.87234(19) 0.21229(10) 0.0433(4) Uani 1 1 d . . .
C19 C 0.14052(8) 1.11148(18) 0.18566(9) 0.0417(4) Uani 1 1 d . . .
C20 C 0.06172(8) 0.9427(2) 0.00219(10) 0.0472(4) Uani 1 1 d . . .
N2 N 0.11737(8) 0.74745(17) 0.25045(9) 0.0529(4) Uani 1 1 d . . .
C21 C 0.01570(8) 0.95506(19) -0.07049(9) 0.0435(4) Uani 1 1 d . . .
C18 C 0.17649(9) 1.2323(2) 0.20837(11) 0.0504(5) Uani 1 1 d . . .
C15 C 0.20359(9) 1.0029(2) 0.30666(11) 0.0541(5) Uani 1 1 d . . .
C7 C 0.14853(9) 0.7098(2) 0.33053(12) 0.0573(5) Uani 1 1 d . . .
C22 C 0.02891(10) 0.9104(2) -0.13614(11) 0.0547(5) Uani 1 1 d . . .
C23 C 0.08417(11) 0.8535(3) -0.13060(14) 0.0650(6) Uani 1 1 d . . .
C17 C 0.22471(9) 1.2370(2) 0.27818(12) 0.0588(5) Uani 1 1 d . . .
C1 C 0.04487(9) 0.7349(2) 0.13245(11) 0.0530(5) Uani 1 1 d . . .
B1 B 0.05242(9) 0.9934(2) 0.08073(11) 0.0454(5) Uani 1 1 d . . .
C12 C 0.13075(10) 0.7698(3) 0.38738(12) 0.0627(6) Uani 1 1 d . . .
C6 C 0.07288(10) 0.6586(2) 0.19846(12) 0.0561(5) Uani 1 1 d . . .
C16 C 0.23920(10) 1.1215(3) 0.32679(12) 0.0628(6) Uani 1 1 d . . .
C24 C 0.12898(12) 0.8399(3) -0.05856(16) 0.0737(7) Uani 1 1 d . . .
C2 C -0.00148(11) 0.6765(3) 0.06979(15) 0.0665(6) Uani 1 1 d . . .
C8 C 0.19143(12) 0.6041(3) 0.34735(17) 0.0809(8) Uani 1 1 d . . .
C3 C -0.01740(13) 0.5391(3) 0.07856(18) 0.0790(8) Uani 1 1 d . . .
C25 C 0.11785(10) 0.8850(3) 0.00594(13) 0.0650(6) Uani 1 1 d . . .
C4 C 0.01258(15) 0.4624(3) 0.1466(2) 0.0898(9) Uani 1 1 d . . .
C5 C 0.05837(13) 0.5201(3) 0.20866(18) 0.0773(7) Uani 1 1 d . . .
C11 C 0.15665(13) 0.7225(4) 0.46334(14) 0.0840(8) Uani 1 1 d . . .
C10 C 0.19783(15) 0.6157(4) 0.48010(18) 0.0985(11) Uani 1 1 d . . .
C9 C 0.21577(15) 0.5570(4) 0.4232(2) 0.1031(11) Uani 1 1 d . . .
H1 H 0.1657(8) 1.314(2) 0.1752(11) 0.052(5) Uiso 1 1 d . . .
H2 H -0.0008(10) 0.921(2) -0.1823(13) 0.067(7) Uiso 1 1 d . . .
H3 H -0.0493(9) 0.500(2) 0.0356(12) 0.062(6) Uiso 1 1 d . . .
H4 H 0.2134(9) 0.929(2) 0.3428(12) 0.064(6) Uiso 1 1 d . . .
H5 H 0.2745(11) 1.120(3) 0.3846(14) 0.085(7) Uiso 1 1 d . . .
H6 H 0.2521(9) 1.326(2) 0.2939(11) 0.060(6) Uiso 1 1 d . . .
H7 H 0.1508(10) 0.879(2) 0.0628(14) 0.073(7) Uiso 1 1 d . . .
H8 H 0.1699(13) 0.798(3) -0.0469(15) 0.101(9) Uiso 1 1 d . . .
H9 H -0.0026(10) 0.373(3) 0.1477(13) 0.077(7) Uiso 1 1 d . . .
H10 H -0.0209(11) 0.739(3) 0.0345(14) 0.079(8) Uiso 1 1 d . . .
H11 H 0.0919(14) 0.826(3) -0.1697(17) 0.111(10) Uiso 1 1 d . . .
H12 H 0.0976(10) 0.841(3) 0.3720(13) 0.072(7) Uiso 1 1 d . . .
H13 H 0.2040(11) 0.562(3) 0.3006(14) 0.084(7) Uiso 1 1 d . . .
H14 H 0.0822(11) 0.475(3) 0.2608(15) 0.090(8) Uiso 1 1 d . . .
H15 H 0.2429(16) 0.481(4) 0.4251(18) 0.129(12) Uiso 1 1 d . . .
H16 H 0.2181(17) 0.578(4) 0.535(2) 0.155(14) Uiso 1 1 d . . .
H18 H 0.1390(13) 0.767(3) 0.4963(16) 0.095(9) Uiso 1 1 d . . .


_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 C19 1.311(2) . ?
O1 B1 1.518(2) . ?
N1 C13 1.321(2) . ?
N1 C1 1.400(2) . ?
N1 B1 1.594(2) . ?
C14 C15 1.385(3) . ?
C14 C19 1.433(2) . ?
C14 C13 1.447(2) . ?
C13 N2 1.366(2) . ?
C19 C18 1.397(3) . ?
C20 C21 1.396(2) . ?
C20 C25 1.404(3) . ?
C20 B1 1.605(3) . ?
N2 C6 1.418(3) . ?
N2 C7 1.439(2) . ?
C21 C22 1.410(2) . ?
C21 B1 1.617(3) 5_575 ?
C18 C17 1.381(3) . ?
C15 C16 1.372(3) . ?
C7 C12 1.375(3) . ?
C7 C8 1.377(3) . ?
C22 C23 1.374(3) . ?
C23 C24 1.377(4) . ?
C17 C16 1.378(3) . ?
C1 C6 1.366(3) . ?
C1 C2 1.391(3) . ?
B1 C21 1.617(3) 5_575 ?
C12 C11 1.386(3) . ?
C6 C5 1.386(3) . ?
C24 C25 1.367(3) . ?
C2 C3 1.380(4) . ?
C8 C9 1.382(4) . ?
C3 C4 1.403(4) . ?
C4 C5 1.376(4) . ?
C11 C10 1.357(5) . ?
C10 C9 1.372(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
C19 O1 B1 127.42(14) . . ?
C13 N1 C1 108.11(15) . . ?
C13 N1 B1 126.97(14) . . ?
C1 N1 B1 124.92(15) . . ?
C15 C14 C19 118.73(17) . . ?
C15 C14 C13 125.50(17) . . ?
C19 C14 C13 115.71(15) . . ?
N1 C13 N2 110.71(16) . . ?
N1 C13 C14 121.33(15) . . ?
N2 C13 C14 127.90(16) . . ?
O1 C19 C18 118.15(16) . . ?
O1 C19 C14 123.91(15) . . ?
C18 C19 C14 117.94(16) . . ?
C21 C20 C25 118.49(17) . . ?
C21 C20 B1 122.04(16) . . ?
C25 C20 B1 119.47(17) . . ?
C13 N2 C6 106.28(16) . . ?
C13 N2 C7 130.83(17) . . ?
C6 N2 C7 122.07(16) . . ?
C20 C21 C22 117.64(17) . . ?
C20 C21 B1 122.54(15) . 5_575 ?
C22 C21 B1 119.65(16) . 5_575 ?
C17 C18 C19 121.05(19) . . ?
C16 C15 C14 122.20(19) . . ?
C12 C7 C8 121.5(2) . . ?
C12 C7 N2 119.51(18) . . ?
C8 C7 N2 118.7(2) . . ?
C23 C22 C21 122.5(2) . . ?
C22 C23 C24 119.4(2) . . ?
C16 C17 C18 120.77(19) . . ?
C6 C1 C2 121.1(2) . . ?
C6 C1 N1 107.79(17) . . ?
C2 C1 N1 131.1(2) . . ?
O1 B1 N1 104.54(14) . . ?
O1 B1 C20 109.93(14) . . ?
N1 B1 C20 109.08(16) . . ?
O1 B1 C21 108.42(16) . 5_575 ?
N1 B1 C21 109.19(14) . 5_575 ?
C20 B1 C21 115.15(15) . 5_575 ?
C7 C12 C11 119.2(2) . . ?
C1 C6 C5 123.9(2) . . ?
C1 C6 N2 107.09(17) . . ?
C5 C6 N2 129.0(2) . . ?
C15 C16 C17 119.21(19) . . ?
C25 C24 C23 119.3(2) . . ?
C3 C2 C1 116.4(3) . . ?
C7 C8 C9 118.2(3) . . ?
C2 C3 C4 121.4(3) . . ?
C24 C25 C20 122.6(2) . . ?
C5 C4 C3 122.2(3) . . ?
C4 C5 C6 115.0(3) . . ?
C10 C11 C12 119.7(3) . . ?
C11 C10 C9 120.9(3) . . ?
C10 C9 C8 120.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.043
