# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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data_dnp_037x
_database_code_depnum_ccdc_archive 'CCDC 1836979'
_audit_update_record             
;
2018-04-13 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

_database_code_CSD               ?

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H26 B Be I N6 O2'
_chemical_formula_weight         493.16

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'
Be Be 0.0005 0.0002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.4590(6)
_cell_length_b                   9.8300(4)
_cell_length_c                   15.3574(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2182.78(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    5365
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      30.4

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.491
_shelx_estimated_absorpt_T_min   0.680
_shelx_estimated_absorpt_T_max   0.841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.43
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   
; 
 BRUKER AXS SMART APEX 2 Vers. 3.0-2009
 R.H. Blessing, Acta Cryst. (1995) A51 33-38 
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Triumph Goebel mirror'
_diffrn_measurement_device_type  
; 
 Bruker D8 KAPPA series II with APEX II area detector system
;
_diffrn_measurement_method       
;
 Data collection strategy APEX 2/COSMO
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            14005
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.934
_diffrn_reflns_theta_max         30.506
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3429
_reflns_number_gt                2896
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'BRUKER D8 KAPPA APEX 2 (3.0-2009)'
_computing_cell_refinement       'BRUKER D8 KAPPA APEX 2 (3.0-2009)'
_computing_data_reduction        'BRUKER D8 KAPPA APEX 2 (3.0-2009)'
_computing_structure_solution    'BRUKER D8 KAPPA APEX 2 (3.0-2009)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'

_refine_special_details          
;
 Treatment of hydrogen atoms:    
 Riding model on idealized geometries 
 with the 1.2 fold isotropic displacement 
 parameters of the equivalent Uij of the 
 corresponding carbon atom.

 C7 is disorder over two position with SOF 0.5
 Solvent THF molecule ist disorder via a mirror-plane
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0129P)²+4.7348P] 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_number_reflns         3429
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0743
_refine_ls_wR_factor_gt          0.0711
_refine_ls_goodness_of_fit_ref   1.190
_refine_ls_restrained_S_all      1.190
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.95020(2) 0.2500 0.85271(2) 0.01744(7) Uani 1 2 d S T P . .
B1 B 0.9142(3) 0.2500 0.4502(3) 0.0208(9) Uani 1 2 d S T P . .
H1B H 0.9815 0.2500 0.4654 0.025 Uiso 1 2 calc R U P . .
Be1 Be 0.7318(3) 0.2500 0.4098(3) 0.0182(9) Uani 1 2 d S T P A .
O1 O 0.62445(18) 0.2500 0.38576(18) 0.0213(6) Uani 1 2 d S T P . .
N1 N 0.79505(16) 0.3855(3) 0.37121(15) 0.0267(5) Uani 1 1 d . . . . .
N2 N 0.88668(15) 0.3751(3) 0.39434(15) 0.0248(5) Uani 1 1 d . . . . .
N3 N 0.7588(2) 0.2500 0.5180(2) 0.0165(6) Uani 1 2 d S T P . .
N4 N 0.8526(2) 0.2500 0.5308(2) 0.0170(6) Uani 1 2 d S T P A .
C1 C 0.7889(2) 0.4921(4) 0.3173(2) 0.0410(9) Uani 1 1 d . . . . .
H1 H 0.7332 0.5240 0.2916 0.049 Uiso 1 1 calc R U . . .
C2 C 0.8760(2) 0.5496(5) 0.3043(3) 0.0487(11) Uani 1 1 d . . . . .
H2 H 0.8911 0.6255 0.2687 0.058 Uiso 1 1 calc R U . . .
C3 C 0.9352(2) 0.4728(4) 0.3540(2) 0.0368(8) Uani 1 1 d . . . . .
H3 H 1.0000 0.4867 0.3590 0.044 Uiso 1 1 calc R U . . .
C4 C 0.7187(3) 0.2500 0.5962(2) 0.0178(7) Uani 1 2 d S T P A .
H4 H 0.6538 0.2500 0.6062 0.021 Uiso 1 2 d R U P . .
C5 C 0.7857(3) 0.2500 0.6609(2) 0.0229(8) Uani 1 2 d S T P . .
H5 H 0.7761 0.2500 0.7220 0.028 Uiso 1 2 d R U P A .
C6 C 0.8705(3) 0.2500 0.6165(2) 0.0183(7) Uani 1 2 d S T P A .
H6 H 0.9301 0.2500 0.6426 0.022 Uiso 1 2 d R U P . .
C7 C 0.5612(4) 0.1343(7) 0.4159(5) 0.0293(14) Uani 0.5 1 d . . P A 1
H7A H 0.5793 0.0510 0.3880 0.035 Uiso 0.5 1 d R U P A 1
H7B H 0.5612 0.1229 0.4800 0.035 Uiso 0.5 1 d R U P A 1
C8 C 0.4712(2) 0.1729(5) 0.3872(2) 0.0475(10) Uani 1 1 d . . . . .
H8A H 0.4594 0.1681 0.3192 0.057 Uiso 0.5 1 d R U P A 2
H8B H 0.4154 0.1542 0.4150 0.057 Uiso 0.5 1 d R U P A 2
H8C H 0.4529 0.1383 0.4430 0.057 Uiso 0.5 1 d R U P A 1
H8D H 0.4297 0.1383 0.3437 0.057 Uiso 0.5 1 d R U P A 1
C7' C 0.5731(4) 0.1331(7) 0.3654(5) 0.0291(14) Uani 0.5 1 d . . P A 2
H7'A H 0.5924 0.0577 0.4007 0.035 Uiso 0.5 1 d R U P A 2
H7'B H 0.5800 0.1092 0.3051 0.035 Uiso 0.5 1 d R U P A 2
O2 O 0.6548(3) 0.3405(6) 0.1423(3) 0.0299(10) Uani 0.5 1 d . . P . .
C9 C 0.7101(4) 0.2500 0.0066(3) 0.0460(14) Uani 1 2 d S T P . .
H9A H 0.6608 0.2500 -0.0381 0.055 Uiso 1 2 calc R U P . .
H9B H 0.7710 0.2500 -0.0228 0.055 Uiso 1 2 calc R U P . .
C10 C 0.7007(2) 0.3718(4) 0.0661(2) 0.0420(8) Uani 1 1 d . . . . .
H10A H 0.7631 0.4068 0.0804 0.050 Uiso 1 1 calc R U . . .
H10B H 0.6667 0.4447 0.0353 0.050 Uiso 1 1 calc R U . . .
C11 C 0.6868(6) 0.2066(8) 0.1552(5) 0.0349(18) Uani 0.5 1 d . . P . .
H11A H 0.6418 0.1563 0.1916 0.042 Uiso 0.5 1 calc R U P . .
H11B H 0.7464 0.2094 0.1870 0.042 Uiso 0.5 1 calc R U P . .


_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 N4 1.525(5) . ?
B1 N2 1.551(4) . ?
B1 N2 1.551(4) 8_565 ?
Be1 O1 1.595(6) . ?
Be1 N3 1.707(6) . ?
Be1 N1 1.721(4) 8_565 ?
Be1 N1 1.721(4) . ?
O1 C7' 1.403(6) . ?
O1 C7' 1.403(6) 8_565 ?
O1 C7 1.531(6) 8_565 ?
O1 C7 1.531(6) . ?
N1 C1 1.338(4) . ?
N1 N2 1.375(3) . ?
N2 C3 1.342(4) . ?
N3 C4 1.334(5) . ?
N3 N4 1.370(4) . ?
N4 C6 1.341(5) . ?
C1 C2 1.395(4) . ?
C2 C3 1.372(5) . ?
C4 C5 1.388(5) . ?
C5 C6 1.402(5) . ?
C7 C8 1.426(7) . ?
C8 C8 1.515(9) 8_565 ?
C8 C7' 1.562(7) . ?
O2 C10 1.380(6) . ?
O2 C11 1.410(9) . ?
C9 C10 1.512(5) 8_565 ?
C9 C10 1.512(5) . ?
C11 C10 1.583(9) 8_565 ?

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
N4 B1 N2 107.4(2) . . ?
N4 B1 N2 107.4(2) . 8_565 ?
N2 B1 N2 104.8(3) . 8_565 ?
O1 Be1 N3 116.6(3) . . ?
O1 Be1 N1 115.9(2) . 8_565 ?
N3 Be1 N1 102.3(2) . 8_565 ?
O1 Be1 N1 115.9(2) . . ?
N3 Be1 N1 102.3(2) . . ?
N1 Be1 N1 101.4(3) 8_565 . ?
C7' O1 C7' 109.9(6) . 8_565 ?
C7 O1 C7 96.0(5) 8_565 . ?
C7' O1 Be1 124.5(3) . . ?
C7' O1 Be1 124.5(3) 8_565 . ?
C7 O1 Be1 120.7(3) 8_565 . ?
C7 O1 Be1 120.7(3) . . ?
C1 N1 N2 106.4(2) . . ?
C1 N1 Be1 141.6(3) . . ?
N2 N1 Be1 111.4(2) . . ?
C3 N2 N1 109.3(2) . . ?
C3 N2 B1 133.6(3) . . ?
N1 N2 B1 116.7(2) . . ?
C4 N3 N4 107.5(3) . . ?
C4 N3 Be1 141.0(3) . . ?
N4 N3 Be1 111.5(3) . . ?
C6 N4 N3 109.4(3) . . ?
C6 N4 B1 133.2(3) . . ?
N3 N4 B1 117.5(3) . . ?
N1 C1 C2 110.2(3) . . ?
C3 C2 C1 105.1(3) . . ?
N2 C3 C2 109.0(3) . . ?
N3 C4 C5 109.9(3) . . ?
C4 C5 C6 105.2(3) . . ?
N4 C6 C5 108.0(3) . . ?
C8 C7 O1 104.7(5) . . ?
C7 C8 C8 105.5(3) . 8_565 ?
C8 C8 C7' 104.5(3) 8_565 . ?
O1 C7' C8 104.2(5) . . ?
C10 O2 C11 99.7(6) . . ?
C10 C9 C10 104.7(4) 8_565 . ?
O2 C10 C9 112.3(4) . . ?
O2 C11 C10 112.0(7) . 8_565 ?

_refine_diff_density_max         0.597
_refine_diff_density_min         -1.150
_refine_diff_density_rms         0.103

_shelxl_version_number           2013-4

