# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_1
_audit_block_doi                 10.5517/ccxpmy4
_database_code_depnum_ccdc_archive 'CCDC 854947'
_audit_update_record             
;
2017-11-15 deposited with the CCDC.
2017-11-23 downloaded from the CCDC.
;
_audit_creation_date             2017-11-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '0.17(B5 H4 O10), 0.17(C7 H13 N2)'
_chemical_formula_sum            'C1.217 H2.957 B0.87 N0.348 O1.739'
_chemical_formula_weight         59.71
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           ' P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   11.366(2)
_cell_length_b                   11.650(2)
_cell_length_c                   11.659(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1543.9(5)
_cell_formula_units_Z            23
_cell_measurement_temperature    293(2)
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.4767
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712.5201
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15030
_diffrn_reflns_theta_full        25.0670
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         3.05
_diffrn_measured_fraction_theta_full 0.9978
_diffrn_measured_fraction_theta_max 0.9978
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.999
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              13
_reflns_limit_l_min              -13
_reflns_number_gt                2091
_reflns_number_total             2729
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.9528
_refine_diff_density_min         -0.3599
_refine_diff_density_rms         0.0873
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   1(7)
_refine_ls_d_res_high            0.8388
_refine_ls_d_res_low             6.6719
_refine_ls_goodness_of_fit_ref   1.1557
_refine_ls_matrix_type           full
_refine_ls_number_constraints    27
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2729
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0790
_refine_ls_restrained_S_all      1.1557
_refine_ls_shift/su_max          0.7319
_refine_ls_shift/su_mean         0.0637
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1424P)²+0.4329P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2206
_refine_ls_wR_factor_ref         0.2367
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7)
2.c Tetrahedral OH refined with riding coordinates:
 O1(H1), O2(H2), O3(H3), O4(H4)
2.d Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C2(H2a,H2b,H2c), C4(H4a,H4b,H4c)
;
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
B1 B -0.0635(4) 0.8827(4) 0.1874(5) 0.0418(12) Uani 1.000000
B2 B -0.0596(4) 1.0861(4) 0.1871(5) 0.0420(12) Uani 1.000000
B3 B 0.1201(4) 0.9834(4) 0.2400(4) 0.0348(9) Uani 1.000000
B4 B 0.3063(4) 0.9314(4) 0.1425(4) 0.0391(11) Uani 1.000000
B5 B 0.3008(4) 0.9330(5) 0.3464(5) 0.0408(11) Uani 1.000000
O1 O -0.1290(3) 0.7868(3) 0.1693(3) 0.0574(10) Uani 1.000000
H1 H -0.1915(3) 0.8046(3) 0.1389(3) 0.0861(15) Uiso 1.000000
O2 O -0.1229(3) 1.1837(3) 0.1703(4) 0.0631(11) Uani 1.000000
H2 H -0.1860(3) 1.1677(3) 0.1401(4) 0.0947(17) Uiso 1.000000
O3 O 0.3751(3) 0.9161(3) 0.0480(3) 0.0526(9) Uani 1.000000
H3 H 0.4373(3) 0.8859(3) 0.0670(3) 0.0789(14) Uiso 1.000000
O4 O 0.3624(3) 0.9166(4) 0.4440(3) 0.0621(11) Uani 1.000000
H4 H 0.4261(3) 0.8873(4) 0.4286(3) 0.0932(16) Uiso 1.000000
O5 O -0.1136(3) 0.9855(3) 0.1546(3) 0.0553(9) Uani 1.000000
O6 O 0.0485(2) 1.0865(2) 0.2356(2) 0.0387(7) Uani 1.000000
O7 O 0.0439(2) 0.8794(2) 0.2364(3) 0.0398(7) Uani 1.000000
O8 O 0.1984(2) 0.9792(3) 0.1386(2) 0.0409(7) Uani 1.000000
O9 O 0.3539(3) 0.8985(3) 0.2462(3) 0.0503(8) Uani 1.000000
O10 O 0.1911(2) 0.9805(3) 0.3448(2) 0.0384(7) Uani 1.000000
N1 N 0.3099(6) 0.4376(5) 0.5454(5) 0.0828(17) Uani 1.000000
N2 N 0.2132(4) 0.5880(5) 0.6010(4) 0.0661(13) Uani 1.000000
C1 C 0.3461(6) 0.3229(5) 0.5195(7) 0.0774(19) Uani 1.000000
H1a H 0.335(4) 0.2752(11) 0.5857(16) 0.116(3) Uiso 1.000000
H1b H 0.300(3) 0.2938(17) 0.457(3) 0.116(3) Uiso 1.000000
H1c H 0.4278(14) 0.3228(8) 0.499(4) 0.116(3) Uiso 1.000000
C2 C 0.1352(7) 0.3992(7) 0.6432(7) 0.095(2) Uani 1.000000
H2a H 0.105(4) 0.347(4) 0.5866(15) 0.143(4) Uiso 1.000000
H2b H 0.1688(15) 0.356(4) 0.705(3) 0.143(4) Uiso 1.000000
H2c H 0.072(3) 0.4465(8) 0.671(5) 0.143(4) Uiso 1.000000
C3 C 0.1274(9) 0.6614(11) 0.6521(13) 0.160(6) Uani 1.000000
H3a H 0.0519(9) 0.6360(11) 0.6228(13) 0.192(7) Uiso 1.000000
H3b H 0.1277(9) 0.6433(11) 0.7333(13) 0.192(7) Uiso 1.000000
C4 C 0.1262(11) 0.7691(9) 0.6459(15) 0.185(7) Uani 1.000000
H4a H 0.097(9) 0.8004(9) 0.716(4) 0.278(11) Uiso 1.000000
H4b H 0.205(2) 0.7967(10) 0.633(10) 0.278(11) Uiso 1.000000
H4c H 0.076(8) 0.7925(9) 0.584(6) 0.278(11) Uiso 1.000000
C5 C 0.2215(7) 0.4683(8) 0.5939(6) 0.084(2) Uani 1.000000
C6 C 0.3804(6) 0.5389(8) 0.5058(6) 0.091(2) Uani 1.000000
H6 H 0.4520(6) 0.5395(8) 0.4672(6) 0.109(3) Uiso 1.000000
C7 C 0.3177(7) 0.6243(8) 0.5383(8) 0.099(3) Uani 1.000000
H7 H 0.3367(7) 0.7005(8) 0.5236(8) 0.118(3) Uiso 1.000000


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 O1 1.359(6) . ?
B1 O5 1.380(6) . ?
B1 O7 1.348(6) . ?
B2 O2 1.360(6) . ?
B2 O5 1.376(6) . ?
B2 O6 1.353(6) . ?
B3 O6 1.452(5) . ?
B3 O7 1.490(5) . ?
B3 O8 1.481(5) . ?
B3 O10 1.464(5) . ?
B4 O3 1.362(6) . ?
B4 O8 1.348(6) . ?
B4 O9 1.379(6) . ?
B5 O4 1.349(6) . ?
B5 O9 1.375(6) . ?
B5 O10 1.364(6) . ?
O1 H1 0.8200 . ?
O2 H2 0.8200 . ?
O3 H3 0.8200 . ?
O4 H4 0.8200 . ?
N1 C1 1.430(9) . ?
N1 C5 1.207(10) . ?
N1 C6 1.499(10) . ?
N2 C3 1.427(11) . ?
N2 C5 1.400(10) . ?
N2 C7 1.457(10) . ?
C1 H1a 0.9600 . ?
C1 H1b 0.9600 . ?
C1 H1c 0.9600 . ?
C2 H2a 0.9600 . ?
C2 H2b 0.9600 . ?
C2 H2c 0.9600 . ?
C2 C5 1.393(9) . ?
C3 H3a 0.9700 . ?
C3 H3b 0.9700 . ?
C3 C4 1.257(14) . ?
C4 H4a 0.9600 . ?
C4 H4b 0.9600 . ?
C4 H4c 0.9600 . ?
C6 H6 0.9300 . ?
C6 C7 1.282(11) . ?
C7 H7 0.9300 . ?

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 O1 116.4(4) . . ?
O7 B1 O1 122.6(4) . . ?
O7 B1 O5 121.1(4) . . ?
O5 B2 O2 115.9(4) . . ?
O6 B2 O2 122.6(4) . . ?
O6 B2 O5 121.5(4) . . ?
O7 B3 O6 110.3(3) . . ?
O8 B3 O6 109.6(4) . . ?
O8 B3 O7 107.4(3) . . ?
O10 B3 O6 111.0(3) . . ?
O10 B3 O7 109.0(4) . . ?
O10 B3 O8 109.5(3) . . ?
O8 B4 O3 123.3(4) . . ?
O9 B4 O3 116.6(4) . . ?
O9 B4 O8 120.0(4) . . ?
O9 B5 O4 116.6(4) . . ?
O10 B5 O4 122.9(4) . . ?
O10 B5 O9 120.5(4) . . ?
H1 O1 B1 109.5 . . ?
H2 O2 B2 109.5 . . ?
H3 O3 B4 109.5 . . ?
H4 O4 B5 109.5 . . ?
B2 O5 B1 118.6(3) . . ?
B3 O6 B2 121.4(3) . . ?
B3 O7 B1 121.0(3) . . ?
B4 O8 B3 122.3(3) . . ?
B5 O9 B4 119.5(3) . . ?
B5 O10 B3 121.7(3) . . ?
C5 N1 C1 128.0(8) . . ?
C6 N1 C1 121.1(7) . . ?
C6 N1 C5 110.9(7) . . ?
C5 N2 C3 131.9(7) . . ?
C7 N2 C3 126.3(7) . . ?
C7 N2 C5 101.8(6) . . ?
H1a C1 N1 109.5 . . ?
H1b C1 N1 109.5 . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 N1 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?
H2b C2 H2a 109.5 . . ?
H2c C2 H2a 109.5 . . ?
H2c C2 H2b 109.5 . . ?
C5 C2 H2a 109.5 . . ?
C5 C2 H2b 109.5 . . ?
C5 C2 H2c 109.5 . . ?
H3a C3 N2 105.9(5) . . ?
H3b C3 N2 105.9(7) . . ?
H3b C3 H3a 106.250192676(15) . . ?
C4 C3 N2 125.6(13) . . ?
C4 C3 H3a 105.9(8) . . ?
C4 C3 H3b 105.9(11) . . ?
H4a C4 C3 109.5 . . ?
H4b C4 C3 109.5 . . ?
H4b C4 H4a 109.5 . . ?
H4c C4 C3 109.5 . . ?
H4c C4 H4a 109.5 . . ?
H4c C4 H4b 109.5 . . ?
N2 C5 N1 112.3(6) . . ?
C2 C5 N1 127.4(9) . . ?
C2 C5 N2 120.3(8) . . ?
H6 C6 N1 128.6(4) . . ?
C7 C6 N1 102.8(6) . . ?
C7 C6 H6 128.6(5) . . ?
C6 C7 N2 112.1(7) . . ?
H7 C7 N2 123.9(4) . . ?
H7 C7 C6 123.9(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
