# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_Prosp14mz088_0m
_database_code_depnum_ccdc_archive 'CCDC 1421389'
_audit_update_record             
;
2016-12-09 deposited with the CCDC.
2016-12-12 downloaded from the CCDC.
;
_publcif_datablock.id            {58b8623f-414b-402a-bb91-2120daf4e90e}

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 '1-boranocaboxylic acid-3,5,7-Triaza-1-azoniatricyclo[3.3.1.1(3,7)]decane' 
;
_chemical_name_common            'Hexamethylenetetramine Boranocarboxylic acid'
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H14 B N4 O2'
_chemical_formula_sum            'C7 H14 B N4 O2'
_chemical_formula_weight         197.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   10.4040(4)
_cell_length_b                   11.3367(4)
_cell_length_c                   16.7032(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1970.09(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9935
_cell_measurement_theta_min      2.3211
_cell_measurement_theta_max      26.4304

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.804
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3817
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'Apex2 v2014.1-0 (Bruker, 2014)'

_exptl_special_details           ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  'Bruker AXS X8 Prospector CCD diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21034
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.296
_diffrn_reflns_theta_max         66.670
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             1727
_reflns_number_gt                1513
_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       'Apex2 v2014.1-0 (Bruker, 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0495P)²+0.8362P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1727
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0966
_refine_ls_wR_factor_gt          0.0920
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001

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
N1 N 0.06105(10) 0.62648(9) 0.17620(6) 0.0133(3) Uani 1 1 d . . . . .
N2 N -0.00136(10) 0.63518(10) 0.03469(7) 0.0161(3) Uani 1 1 d . . . . .
N4 N 0.20655(10) 0.71238(10) 0.07669(7) 0.0171(3) Uani 1 1 d . . . . .
N3 N 0.01032(11) 0.81631(9) 0.11345(7) 0.0168(3) Uani 1 1 d . . . . .
C1 C 0.11979(13) 0.60041(12) 0.33049(8) 0.0162(3) Uani 1 1 d . . . . .
C5 C 0.19896(12) 0.64448(11) 0.14971(8) 0.0157(3) Uani 1 1 d . . . . .
H5A H 0.2460 0.6850 0.1917 0.019 Uiso 1 1 calc R U . . .
H5B H 0.2392 0.5683 0.1414 0.019 Uiso 1 1 calc R U . . .
C6 C 0.13449(13) 0.65076(12) 0.01311(8) 0.0178(3) Uani 1 1 d . . . . .
H6A H 0.1402 0.6958 -0.0362 0.021 Uiso 1 1 calc R U . . .
H6B H 0.1731 0.5741 0.0037 0.021 Uiso 1 1 calc R U . . .
C4 C 0.00172(12) 0.74754(11) 0.18708(8) 0.0157(3) Uani 1 1 d . . . . .
H4A H -0.0878 0.7391 0.2023 0.019 Uiso 1 1 calc R U . . .
H4B H 0.0459 0.7889 0.2298 0.019 Uiso 1 1 calc R U . . .
C3 C -0.05806(12) 0.75211(12) 0.04879(8) 0.0177(3) Uani 1 1 d . . . . .
H3A H -0.1478 0.7431 0.0633 0.021 Uiso 1 1 calc R U . . .
H3B H -0.0541 0.7979 -0.0002 0.021 Uiso 1 1 calc R U . . .
C2 C -0.00974(12) 0.56677(12) 0.10759(8) 0.0161(3) Uani 1 1 d . . . . .
H2A H 0.0268 0.4892 0.0985 0.019 Uiso 1 1 calc R U . . .
H2B H -0.0994 0.5566 0.1220 0.019 Uiso 1 1 calc R U . . .
C7 C 0.14678(14) 0.82769(12) 0.09031(8) 0.0190(3) Uani 1 1 d . . . . .
H7A H 0.1530 0.8745 0.0418 0.023 Uiso 1 1 calc R U . . .
H7B H 0.1931 0.8688 0.1323 0.023 Uiso 1 1 calc R U . . .
O1 O 0.17654(9) 0.69473(8) 0.33540(6) 0.0198(3) Uani 1 1 d . . . . .
O2 O 0.11502(10) 0.53410(8) 0.39783(5) 0.0230(3) Uani 1 1 d . . . . .
H2 H 0.0780 0.4718 0.3882 0.035 Uiso 1 1 calc R U . . .
B1 B 0.05102(14) 0.54396(13) 0.25305(9) 0.0165(3) Uani 1 1 d . . . . .
H1A H 0.0962(4) 0.4574(8) 0.23947(16) 0.020 Uiso 1 1 calc R U . . .
H1B H -0.0521(10) 0.5279(2) 0.26687(16) 0.020 Uiso 1 1 calc R U . . .


_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
N1 C5 1.5154(16) . ?
N1 C4 1.5157(16) . ?
N1 C2 1.5212(16) . ?
N1 B1 1.5918(18) . ?
N2 C2 1.4461(17) . ?
N2 C6 1.4692(17) . ?
N2 C3 1.4699(17) . ?
N4 C5 1.4444(17) . ?
N4 C7 1.4653(18) . ?
N4 C6 1.4757(17) . ?
N3 C4 1.4589(17) . ?
N3 C7 1.4771(18) . ?
N3 C3 1.4840(17) . ?
C1 O1 1.2242(16) . ?
C1 O2 1.3537(16) . ?
C1 B1 1.6107(19) . ?

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
C5 N1 C4 107.38(9) . . ?
C5 N1 C2 107.36(9) . . ?
C4 N1 C2 107.22(9) . . ?
C5 N1 B1 112.13(10) . . ?
C4 N1 B1 114.13(10) . . ?
C2 N1 B1 108.32(9) . . ?
C2 N2 C6 109.21(10) . . ?
C2 N2 C3 108.94(10) . . ?
C6 N2 C3 108.48(10) . . ?
C5 N4 C7 108.73(10) . . ?
C5 N4 C6 109.12(10) . . ?
C7 N4 C6 108.57(10) . . ?
C4 N3 C7 109.04(10) . . ?
C4 N3 C3 108.79(10) . . ?
C7 N3 C3 108.25(10) . . ?
O1 C1 O2 116.55(11) . . ?
O1 C1 B1 127.96(11) . . ?
O2 C1 B1 115.49(11) . . ?
N4 C5 N1 111.72(10) . . ?
N2 C6 N4 111.66(11) . . ?
N3 C4 N1 110.97(10) . . ?
N2 C3 N3 111.50(10) . . ?
N2 C2 N1 111.50(10) . . ?
N4 C7 N3 111.75(10) . . ?
N1 B1 C1 112.64(10) . . ?

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-4


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
