# 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_av42
_database_code_depnum_ccdc_archive 'CCDC 1031906'
_audit_update_record             
;
2014-10-31 deposited with the CCDC.
2015-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H21 B Cl2 N2 O5 Pd'
_chemical_formula_sum            'C20 H21 B Cl2 N2 O5 Pd'
_chemical_formula_weight         557.50
_chemical_absolute_configuration rmad

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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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                   9.8914(11)
_cell_length_b                   10.6681(12)
_cell_length_c                   22.200(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2342.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    7194
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.92

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    1.053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_process_details   'SABABS; Bruker,2001'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(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  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26164
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         27.98
_reflns_number_total             5483
_reflns_number_gt                5322
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97

_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)+(0.0356P)²+0.3757P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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   0.010(17)
_refine_ls_number_reflns         5483
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0215
_refine_ls_wR_factor_ref         0.0584
_refine_ls_wR_factor_gt          0.0579
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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
B1 B 0.5278(2) 0.2507(2) 0.57806(10) 0.0357(5) Uani 1 1 d . . .
C1 C 0.6455(2) 0.0247(2) 0.45903(10) 0.0477(5) Uani 1 1 d . . .
H1 H 0.7277 0.0755 0.4562 0.057 Uiso 1 1 calc R . .
C2 C 0.6383(2) -0.0421(2) 0.52006(11) 0.0470(5) Uani 1 1 d . . .
H2 H 0.7245 -0.0419 0.5418 0.056 Uiso 1 1 calc R . .
C3 C 0.5261(2) 0.0271(2) 0.55315(9) 0.0397(4) Uani 1 1 d . . .
H3 H 0.4791 -0.0276 0.5818 0.048 Uiso 1 1 calc R . .
C4 C 0.4345(2) 0.0662(2) 0.50117(9) 0.0387(4) Uani 1 1 d . . .
H4 H 0.3806 -0.0057 0.4878 0.046 Uiso 1 1 calc R . .
C5 C 0.3427(2) 0.1752(3) 0.51539(12) 0.0506(6) Uani 1 1 d . . .
H5A H 0.3065 0.2086 0.4781 0.061 Uiso 1 1 calc R . .
H5B H 0.2673 0.1456 0.5395 0.061 Uiso 1 1 calc R . .
C6 C 0.6172(3) -0.1899(3) 0.44286(14) 0.0631(8) Uani 1 1 d . . .
C7 C 0.7399(4) -0.2750(4) 0.4348(2) 0.1019(15) Uani 1 1 d . . .
H7A H 0.7532 -0.2917 0.3927 0.153 Uiso 1 1 calc R . .
H7B H 0.7251 -0.3525 0.4557 0.153 Uiso 1 1 calc R . .
H7C H 0.8187 -0.2344 0.4508 0.153 Uiso 1 1 calc R . .
C8 C 0.4908(4) -0.2456(4) 0.4153(2) 0.0969(14) Uani 1 1 d . . .
H8A H 0.4139 -0.1955 0.4262 0.145 Uiso 1 1 calc R . .
H8B H 0.4785 -0.3295 0.4299 0.145 Uiso 1 1 calc R . .
H8C H 0.4996 -0.2470 0.3722 0.145 Uiso 1 1 calc R . .
C9 C 0.5967(2) 0.3671(2) 0.60931(9) 0.0373(4) Uani 1 1 d . . .
C10 C 0.7103(2) 0.3551(2) 0.64738(9) 0.0366(4) Uani 1 1 d . . .
H10 H 0.7483 0.2767 0.6541 0.044 Uiso 1 1 calc R . .
C11 C 0.7655(2) 0.4609(2) 0.67490(9) 0.0383(4) Uani 1 1 d . . .
C12 C 0.7098(3) 0.5785(2) 0.66681(13) 0.0537(6) Uani 1 1 d . . .
H12 H 0.7448 0.6476 0.6870 0.064 Uiso 1 1 calc R . .
C13 C 0.5995(3) 0.5919(3) 0.62760(16) 0.0698(9) Uani 1 1 d . . .
H13 H 0.5627 0.6707 0.6205 0.084 Uiso 1 1 calc R . .
C14 C 0.5456(3) 0.4874(3) 0.59957(12) 0.0539(6) Uani 1 1 d . . .
H14 H 0.4730 0.4977 0.5734 0.065 Uiso 1 1 calc R . .
C15 C 0.9931(2) 0.4029(2) 0.68831(9) 0.0401(5) Uani 1 1 d . . .
H15 H 0.9900 0.3643 0.6508 0.048 Uiso 1 1 calc R . .
C16 C 1.1193(2) 0.4091(2) 0.72257(9) 0.0388(4) Uani 1 1 d . . .
C17 C 1.2416(2) 0.3641(3) 0.70118(11) 0.0528(6) Uani 1 1 d . . .
H17 H 1.2463 0.3217 0.6646 0.063 Uiso 1 1 calc R . .
C18 C 1.3574(3) 0.3835(3) 0.73558(12) 0.0631(8) Uani 1 1 d . . .
H18 H 1.4408 0.3539 0.7224 0.076 Uiso 1 1 calc R . .
C19 C 1.3473(3) 0.4468(3) 0.78911(12) 0.0625(7) Uani 1 1 d . . .
H19 H 1.4240 0.4610 0.8123 0.075 Uiso 1 1 calc R . .
C20 C 1.2220(2) 0.4899(3) 0.80870(10) 0.0520(6) Uani 1 1 d . . .
H20 H 1.2162 0.5325 0.8452 0.062 Uiso 1 1 calc R . .
Cl1 Cl 0.97194(7) 0.59917(7) 0.88947(3) 0.05544(15) Uani 1 1 d . . .
Cl2 Cl 0.68984(6) 0.55050(8) 0.81612(3) 0.05871(17) Uani 1 1 d . . .
N1 N 0.88637(17) 0.45220(17) 0.71157(7) 0.0373(4) Uani 1 1 d . . .
N2 N 1.10857(17) 0.47131(19) 0.77594(8) 0.0394(4) Uani 1 1 d . . .
O1 O 0.6467(3) -0.0712(2) 0.41599(9) 0.0797(7) Uani 1 1 d . . .
O2 O 0.5922(2) -0.16505(15) 0.50517(9) 0.0633(5) Uani 1 1 d . . .
O3 O 0.58596(16) 0.13363(14) 0.58253(6) 0.0405(3) Uani 1 1 d . . .
O4 O 0.52898(18) 0.10113(17) 0.45476(7) 0.0466(4) Uani 1 1 d . . .
O5 O 0.41112(17) 0.27399(15) 0.54749(8) 0.0470(4) Uani 1 1 d . . .
Pd1 Pd 0.915041(15) 0.519785(16) 0.796775(6) 0.03638(5) Uani 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
B1 O5 1.362(3) . ?
B1 O3 1.378(3) . ?
B1 C9 1.578(3) . ?
C1 O1 1.400(3) . ?
C1 O4 1.415(3) . ?
C1 C2 1.532(3) . ?
C1 H1 0.9800 . ?
C2 O2 1.427(3) . ?
C2 C3 1.522(3) . ?
C2 H2 0.9800 . ?
C3 O3 1.438(3) . ?
C3 C4 1.525(3) . ?
C3 H3 0.9800 . ?
C4 O4 1.440(3) . ?
C4 C5 1.509(3) . ?
C4 H4 0.9800 . ?
C5 O5 1.441(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O1 1.430(4) . ?
C6 O2 1.430(4) . ?
C6 C8 1.514(4) . ?
C6 C7 1.526(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C14 1.396(3) . ?
C9 C10 1.412(3) . ?
C10 C11 1.394(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(3) . ?
C11 N1 1.449(2) . ?
C12 C13 1.403(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.383(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 N1 1.287(3) . ?
C15 C16 1.464(3) . ?
C15 H15 0.9300 . ?
C16 N2 1.362(3) . ?
C16 C17 1.386(3) . ?
C17 C18 1.392(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.391(4) . ?
C19 H19 0.9300 . ?
C20 N2 1.352(3) . ?
C20 H20 0.9300 . ?
Cl1 Pd1 2.2953(6) . ?
Cl2 Pd1 2.2921(6) . ?
N1 Pd1 2.0441(16) . ?
N2 Pd1 2.0362(17) . ?

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
O5 B1 O3 123.7(2) . . ?
O5 B1 C9 116.18(19) . . ?
O3 B1 C9 120.10(18) . . ?
O1 C1 O4 112.5(2) . . ?
O1 C1 C2 105.3(2) . . ?
O4 C1 C2 106.84(18) . . ?
O1 C1 H1 110.7 . . ?
O4 C1 H1 110.7 . . ?
C2 C1 H1 110.7 . . ?
O2 C2 C3 108.9(2) . . ?
O2 C2 C1 103.73(19) . . ?
C3 C2 C1 103.59(18) . . ?
O2 C2 H2 113.2 . . ?
C3 C2 H2 113.2 . . ?
C1 C2 H2 113.2 . . ?
O3 C3 C2 107.60(17) . . ?
O3 C3 C4 111.80(18) . . ?
C2 C3 C4 101.57(17) . . ?
O3 C3 H3 111.8 . . ?
C2 C3 H3 111.8 . . ?
C4 C3 H3 111.8 . . ?
O4 C4 C5 109.9(2) . . ?
O4 C4 C3 103.11(16) . . ?
C5 C4 C3 114.21(18) . . ?
O4 C4 H4 109.8 . . ?
C5 C4 H4 109.8 . . ?
C3 C4 H4 109.8 . . ?
O5 C5 C4 112.61(17) . . ?
O5 C5 H5A 109.1 . . ?
C4 C5 H5A 109.1 . . ?
O5 C5 H5B 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
O1 C6 O2 105.9(2) . . ?
O1 C6 C8 110.3(3) . . ?
O2 C6 C8 108.7(3) . . ?
O1 C6 C7 108.4(3) . . ?
O2 C6 C7 111.2(3) . . ?
C8 C6 C7 112.1(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 117.7(2) . . ?
C14 C9 B1 119.96(19) . . ?
C10 C9 B1 122.38(19) . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 121.40(19) . . ?
C12 C11 N1 117.41(19) . . ?
C10 C11 N1 121.2(2) . . ?
C11 C12 C13 118.9(2) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C9 122.1(2) . . ?
C13 C14 H14 119.0 . . ?
C9 C14 H14 119.0 . . ?
N1 C15 C16 118.18(18) . . ?
N1 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
N2 C16 C17 122.3(2) . . ?
N2 C16 C15 114.06(18) . . ?
C17 C16 C15 123.4(2) . . ?
C16 C17 C18 118.6(2) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C19 C18 C17 119.2(2) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 119.9(2) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
N2 C20 C19 121.5(2) . . ?
N2 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C15 N1 C11 118.49(16) . . ?
C15 N1 Pd1 113.68(13) . . ?
C11 N1 Pd1 127.71(13) . . ?
C20 N2 C16 118.35(19) . . ?
C20 N2 Pd1 128.37(16) . . ?
C16 N2 Pd1 113.24(13) . . ?
C1 O1 C6 111.2(2) . . ?
C2 O2 C6 109.8(2) . . ?
B1 O3 C3 120.78(17) . . ?
C1 O4 C4 109.34(17) . . ?
B1 O5 C5 120.72(18) . . ?
N2 Pd1 N1 80.25(7) . . ?
N2 Pd1 Cl2 173.00(6) . . ?
N1 Pd1 Cl2 95.10(5) . . ?
N2 Pd1 Cl1 93.83(5) . . ?
N1 Pd1 Cl1 173.61(5) . . ?
Cl2 Pd1 Cl1 91.01(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O2 -18.3(3) . . . . ?
O4 C1 C2 O2 101.5(2) . . . . ?
O1 C1 C2 C3 -132.1(2) . . . . ?
O4 C1 C2 C3 -12.3(2) . . . . ?
O2 C2 C3 O3 163.57(17) . . . . ?
C1 C2 C3 O3 -86.5(2) . . . . ?
O2 C2 C3 C4 -78.9(2) . . . . ?
C1 C2 C3 C4 31.1(2) . . . . ?
O3 C3 C4 O4 75.2(2) . . . . ?
C2 C3 C4 O4 -39.3(2) . . . . ?
O3 C3 C4 C5 -44.0(2) . . . . ?
C2 C3 C4 C5 -158.5(2) . . . . ?
O4 C4 C5 O5 -71.8(3) . . . . ?
C3 C4 C5 O5 43.5(3) . . . . ?
O5 B1 C9 C14 -6.6(3) . . . . ?
O3 B1 C9 C14 173.3(2) . . . . ?
O5 B1 C9 C10 173.6(2) . . . . ?
O3 B1 C9 C10 -6.5(3) . . . . ?
C14 C9 C10 C11 1.5(3) . . . . ?
B1 C9 C10 C11 -178.62(19) . . . . ?
C9 C10 C11 C12 1.3(3) . . . . ?
C9 C10 C11 N1 -176.65(18) . . . . ?
C10 C11 C12 C13 -3.3(4) . . . . ?
N1 C11 C12 C13 174.8(3) . . . . ?
C11 C12 C13 C14 2.3(5) . . . . ?
C12 C13 C14 C9 0.6(5) . . . . ?
C10 C9 C14 C13 -2.5(4) . . . . ?
B1 C9 C14 C13 177.7(3) . . . . ?
N1 C15 C16 N2 -1.7(3) . . . . ?
N1 C15 C16 C17 -177.2(2) . . . . ?
N2 C16 C17 C18 -0.1(4) . . . . ?
C15 C16 C17 C18 175.1(3) . . . . ?
C16 C17 C18 C19 -0.3(5) . . . . ?
C17 C18 C19 C20 0.5(5) . . . . ?
C18 C19 C20 N2 -0.2(5) . . . . ?
C16 C15 N1 C11 172.15(19) . . . . ?
C16 C15 N1 Pd1 -4.2(3) . . . . ?
C12 C11 N1 C15 -123.1(3) . . . . ?
C10 C11 N1 C15 54.9(3) . . . . ?
C12 C11 N1 Pd1 52.6(3) . . . . ?
C10 C11 N1 Pd1 -129.29(18) . . . . ?
C19 C20 N2 C16 -0.2(4) . . . . ?
C19 C20 N2 Pd1 177.6(2) . . . . ?
C17 C16 N2 C20 0.4(4) . . . . ?
C15 C16 N2 C20 -175.2(2) . . . . ?
C17 C16 N2 Pd1 -177.7(2) . . . . ?
C15 C16 N2 Pd1 6.7(2) . . . . ?
O4 C1 O1 C6 -105.8(3) . . . . ?
C2 C1 O1 C6 10.2(3) . . . . ?
O2 C6 O1 C1 2.0(3) . . . . ?
C8 C6 O1 C1 119.5(3) . . . . ?
C7 C6 O1 C1 -117.5(3) . . . . ?
C3 C2 O2 C6 130.1(2) . . . . ?
C1 C2 O2 C6 20.3(3) . . . . ?
O1 C6 O2 C2 -14.6(3) . . . . ?
C8 C6 O2 C2 -133.1(3) . . . . ?
C7 C6 O2 C2 103.0(3) . . . . ?
O5 B1 O3 C3 1.4(3) . . . . ?
C9 B1 O3 C3 -178.55(17) . . . . ?
C2 C3 O3 B1 132.6(2) . . . . ?
C4 C3 O3 B1 21.9(3) . . . . ?
O1 C1 O4 C4 101.8(2) . . . . ?
C2 C1 O4 C4 -13.3(2) . . . . ?
C5 C4 O4 C1 155.54(18) . . . . ?
C3 C4 O4 C1 33.4(2) . . . . ?
O3 B1 O5 C5 -2.3(3) . . . . ?
C9 B1 O5 C5 177.6(2) . . . . ?
C4 C5 O5 B1 -20.6(3) . . . . ?
C20 N2 Pd1 N1 175.3(2) . . . . ?
C16 N2 Pd1 N1 -6.85(16) . . . . ?
C20 N2 Pd1 Cl2 -136.0(4) . . . . ?
C16 N2 Pd1 Cl2 41.9(5) . . . . ?
C20 N2 Pd1 Cl1 -2.3(2) . . . . ?
C16 N2 Pd1 Cl1 175.58(15) . . . . ?
C15 N1 Pd1 N2 5.99(17) . . . . ?
C11 N1 Pd1 N2 -169.95(19) . . . . ?
C15 N1 Pd1 Cl2 -168.72(16) . . . . ?
C11 N1 Pd1 Cl2 15.33(18) . . . . ?
C15 N1 Pd1 Cl1 28.3(6) . . . . ?
C11 N1 Pd1 Cl1 -147.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.98
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.061
####################################################################### 
# 
# 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_ax74m
_database_code_depnum_ccdc_archive 'CCDC 1031907'
_audit_update_record             
;
2014-10-31 deposited with the CCDC.
2015-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H18 B N O5'
_chemical_formula_sum            'C14 H18 B N O5'
_chemical_formula_weight         291.10
_chemical_absolute_configuration rm

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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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                   5.3490(6)
_cell_length_b                   14.2059(17)
_cell_length_c                   19.214(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1460.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6404
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      24.11

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(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  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15547
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         26.25
_reflns_number_total             2958
_reflns_number_gt                2800
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97

_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)+(0.0352P)²+0.3277P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(12)
_refine_ls_number_reflns         2958
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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
B1 B 0.9204(5) 0.34504(16) 0.74640(10) 0.0497(5) Uani 1 1 d . . .
C1 C 0.9214(3) 0.43900(13) 0.92764(9) 0.0458(4) Uani 1 1 d . . .
H1 H 0.7437 0.4233 0.9320 0.055 Uiso 1 1 calc R . .
C2 C 1.0818(4) 0.34990(13) 0.92376(9) 0.0468(4) Uani 1 1 d . . .
H2 H 0.9875 0.2924 0.9341 0.056 Uiso 1 1 calc R . .
C3 C 1.1820(4) 0.35243(14) 0.85007(9) 0.0507(5) Uani 1 1 d . . .
H3 H 1.3476 0.3233 0.8466 0.061 Uiso 1 1 calc R . .
C4 C 1.1909(4) 0.45610(14) 0.83549(10) 0.0524(5) Uani 1 1 d . . .
H4 H 1.3375 0.4841 0.8580 0.063 Uiso 1 1 calc R . .
C5 C 1.1910(5) 0.47934(17) 0.75902(10) 0.0642(6) Uani 1 1 d . . .
H5A H 1.1619 0.5463 0.7531 0.077 Uiso 1 1 calc R . .
H5B H 1.3540 0.4649 0.7396 0.077 Uiso 1 1 calc R . .
C6 C 1.1820(4) 0.42872(16) 1.02358(9) 0.0542(5) Uani 1 1 d . . .
C7 C 1.3906(5) 0.4887(2) 1.05072(15) 0.0956(10) Uani 1 1 d . . .
H7A H 1.3265 0.5314 1.0851 0.143 Uiso 1 1 calc R . .
H7B H 1.4628 0.5238 1.0131 0.143 Uiso 1 1 calc R . .
H7C H 1.5161 0.4493 1.0714 0.143 Uiso 1 1 calc R . .
C8 C 1.0481(6) 0.3733(2) 1.07922(11) 0.0911(9) Uani 1 1 d . . .
H8A H 0.9208 0.3351 1.0582 0.137 Uiso 1 1 calc R . .
H8B H 0.9726 0.4159 1.1118 0.137 Uiso 1 1 calc R . .
H8C H 1.1655 0.3337 1.1031 0.137 Uiso 1 1 calc R . .
C9 C 0.7137(4) 0.29270(13) 0.70434(9) 0.0459(4) Uani 1 1 d . . .
C10 C 0.6529(4) 0.31921(13) 0.63676(9) 0.0476(4) Uani 1 1 d . . .
H10 H 0.7369 0.3697 0.6166 0.057 Uiso 1 1 calc R . .
C11 C 0.4712(4) 0.27289(12) 0.59840(9) 0.0448(4) Uani 1 1 d . . .
C12 C 0.3437(4) 0.19907(14) 0.62930(10) 0.0527(5) Uani 1 1 d . . .
H12 H 0.2202 0.1674 0.6045 0.063 Uiso 1 1 calc R . .
C13 C 0.3983(4) 0.17229(14) 0.69631(11) 0.0589(5) Uani 1 1 d . . .
H13 H 0.3101 0.1231 0.7168 0.071 Uiso 1 1 calc R . .
C14 C 0.5825(4) 0.21763(13) 0.73342(9) 0.0527(5) Uani 1 1 d . . .
H14 H 0.6198 0.1980 0.7784 0.063 Uiso 1 1 calc R . .
N1 N 0.4284(4) 0.29562(14) 0.52864(9) 0.0578(5) Uani 1 1 d . . .
H1N H 0.279(4) 0.2740(15) 0.5142(11) 0.061(7) Uiso 1 1 d . . .
H2N H 0.471(4) 0.3531(16) 0.5186(10) 0.064(7) Uiso 1 1 d . . .
O1 O 1.0086(3) 0.48678(9) 0.98758(6) 0.0517(3) Uani 1 1 d . . .
O2 O 1.2787(2) 0.36672(10) 0.97172(6) 0.0554(4) Uani 1 1 d . . .
O3 O 1.0024(3) 0.30601(9) 0.80717(6) 0.0553(3) Uani 1 1 d . . .
O4 O 0.9667(3) 0.49093(9) 0.86720(6) 0.0563(4) Uani 1 1 d . . .
O5 O 1.0044(3) 0.42819(10) 0.72185(6) 0.0640(4) Uani 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
B1 O5 1.349(3) . ?
B1 O3 1.365(2) . ?
B1 C9 1.558(3) . ?
C1 O4 1.397(2) . ?
C1 O1 1.416(2) . ?
C1 C2 1.531(3) . ?
C1 H1 0.9800 . ?
C2 O2 1.420(2) . ?
C2 C3 1.514(3) . ?
C2 H2 0.9800 . ?
C3 O3 1.427(2) . ?
C3 C4 1.500(3) . ?
C3 H3 0.9800 . ?
C4 O4 1.433(3) . ?
C4 C5 1.506(3) . ?
C4 H4 0.9800 . ?
C5 O5 1.426(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O1 1.421(2) . ?
C6 O2 1.427(2) . ?
C6 C7 1.497(3) . ?
C6 C8 1.509(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.391(3) . ?
C9 C14 1.394(3) . ?
C10 C11 1.386(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(3) . ?
C11 N1 1.398(2) . ?
C12 C13 1.374(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
N1 H1N 0.90(2) . ?
N1 H2N 0.87(2) . ?

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
O5 B1 O3 123.2(2) . . ?
O5 B1 C9 118.21(18) . . ?
O3 B1 C9 118.53(18) . . ?
O4 C1 O1 111.46(14) . . ?
O4 C1 C2 107.39(14) . . ?
O1 C1 C2 104.56(14) . . ?
O4 C1 H1 111.1 . . ?
O1 C1 H1 111.1 . . ?
C2 C1 H1 111.1 . . ?
O2 C2 C3 109.87(16) . . ?
O2 C2 C1 104.18(14) . . ?
C3 C2 C1 102.97(15) . . ?
O2 C2 H2 113.0 . . ?
C3 C2 H2 113.0 . . ?
C1 C2 H2 113.0 . . ?
O3 C3 C4 111.54(15) . . ?
O3 C3 C2 106.89(16) . . ?
C4 C3 C2 102.07(15) . . ?
O3 C3 H3 111.9 . . ?
C4 C3 H3 111.9 . . ?
C2 C3 H3 111.9 . . ?
O4 C4 C3 103.48(16) . . ?
O4 C4 C5 109.85(18) . . ?
C3 C4 C5 113.42(16) . . ?
O4 C4 H4 110.0 . . ?
C3 C4 H4 110.0 . . ?
C5 C4 H4 110.0 . . ?
O5 C5 C4 112.12(17) . . ?
O5 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
O5 C5 H5B 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
O1 C6 O2 104.77(13) . . ?
O1 C6 C7 109.00(19) . . ?
O2 C6 C7 108.93(17) . . ?
O1 C6 C8 109.74(18) . . ?
O2 C6 C8 110.18(19) . . ?
C7 C6 C8 113.8(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 117.63(18) . . ?
C10 C9 B1 121.40(17) . . ?
C14 C9 B1 120.97(17) . . ?
C11 C10 C9 122.14(18) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C12 C11 C10 118.49(17) . . ?
C12 C11 N1 120.36(18) . . ?
C10 C11 N1 121.02(18) . . ?
C13 C12 C11 120.45(19) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.54(19) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C9 120.73(17) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C11 N1 H1N 111.2(15) . . ?
C11 N1 H2N 112.7(14) . . ?
H1N N1 H2N 119(2) . . ?
C1 O1 C6 109.44(13) . . ?
C2 O2 C6 106.74(14) . . ?
B1 O3 C3 121.49(16) . . ?
C1 O4 C4 108.44(14) . . ?
B1 O5 C5 120.26(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C1 C2 O2 105.59(16) . . . . ?
O1 C1 C2 O2 -12.93(19) . . . . ?
O4 C1 C2 C3 -9.12(19) . . . . ?
O1 C1 C2 C3 -127.64(15) . . . . ?
O2 C2 C3 O3 161.45(14) . . . . ?
C1 C2 C3 O3 -88.03(17) . . . . ?
O2 C2 C3 C4 -81.34(18) . . . . ?
C1 C2 C3 C4 29.19(19) . . . . ?
O3 C3 C4 O4 74.37(17) . . . . ?
C2 C3 C4 O4 -39.45(18) . . . . ?
O3 C3 C4 C5 -44.6(2) . . . . ?
C2 C3 C4 C5 -158.42(18) . . . . ?
O4 C4 C5 O5 -68.1(2) . . . . ?
C3 C4 C5 O5 47.1(3) . . . . ?
O5 B1 C9 C10 13.3(3) . . . . ?
O3 B1 C9 C10 -168.60(18) . . . . ?
O5 B1 C9 C14 -166.51(18) . . . . ?
O3 B1 C9 C14 11.6(3) . . . . ?
C14 C9 C10 C11 -0.8(3) . . . . ?
B1 C9 C10 C11 179.41(18) . . . . ?
C9 C10 C11 C12 1.3(3) . . . . ?
C9 C10 C11 N1 -174.48(19) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
N1 C11 C12 C13 175.3(2) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C12 C13 C14 C9 1.3(3) . . . . ?
C10 C9 C14 C13 -0.5(3) . . . . ?
B1 C9 C14 C13 179.31(18) . . . . ?
O4 C1 O1 C6 -122.85(16) . . . . ?
C2 C1 O1 C6 -7.14(19) . . . . ?
O2 C6 O1 C1 24.6(2) . . . . ?
C7 C6 O1 C1 141.03(18) . . . . ?
C8 C6 O1 C1 -93.7(2) . . . . ?
C3 C2 O2 C6 137.94(16) . . . . ?
C1 C2 O2 C6 28.22(19) . . . . ?
O1 C6 O2 C2 -33.1(2) . . . . ?
C7 C6 O2 C2 -149.6(2) . . . . ?
C8 C6 O2 C2 84.9(2) . . . . ?
O5 B1 O3 C3 1.2(3) . . . . ?
C9 B1 O3 C3 -176.80(16) . . . . ?
C4 C3 O3 B1 21.0(2) . . . . ?
C2 C3 O3 B1 131.81(18) . . . . ?
O1 C1 O4 C4 97.81(16) . . . . ?
C2 C1 O4 C4 -16.16(18) . . . . ?
C3 C4 O4 C1 35.29(17) . . . . ?
C5 C4 O4 C1 156.69(15) . . . . ?
O3 B1 O5 C5 1.1(3) . . . . ?
C9 B1 O5 C5 179.15(18) . . . . ?
C4 C5 O5 B1 -25.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H2N O1 0.87(2) 2.35(2) 3.208(2) 167(2) 2_664
N1 H1N N1 0.90(2) 2.27(2) 3.169(2) 172.8(19) 4_456

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.25
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.028
