# Electronic Supplementary Material (ESI) for ChemComm.
# 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. 
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#######################################################################

data_gb_er719
_database_code_depnum_ccdc_archive 'CCDC 1489647'
_audit_update_record             
;
2016-07-01 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;
_audit_creation_date             2016-07-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        gb_ER719
_chemical_formula_moiety         'C9 H20 B N O2'
_chemical_formula_sum            'C9 H20 B N O2'
_chemical_formula_weight         185.07
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1, -y+1, z+1/2'
'-x+1, y+1, z+1/2'

_cell_length_a                   10.1195(6)
_cell_length_b                   29.385(2)
_cell_length_c                   7.4892(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2227.0(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1027
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      19.92
_cell_measurement_theta_min      2.77
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.2624
_exptl_absorpt_correction_T_min  0.2333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1019 before and 0.0507 after correction.
The Ratio of minimum to maximum transmission is 0.8891.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_preparation       'Add amine to borane. Isolate solid'
_exptl_crystal_recrystallization_method 
'Melt Solid compound and slowly cool to RT'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.0791
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8760
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.123
_diffrn_reflns_theta_min         1.386
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                1716
_reflns_number_total             2442
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2442
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²+0.1250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.1063
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 B1(H1)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O1 O 0.3430(2) 0.38578(7) 0.3889(3) 0.0220(5) Uani 1 1 d . . . . .
O2 O 0.3620(2) 0.36779(7) 0.6913(3) 0.0220(5) Uani 1 1 d . . . . .
N1 N 0.5585(2) 0.40268(8) 0.5377(3) 0.0210(6) Uani 1 1 d . . . . .
H1A H 0.5940 0.3900 0.6376 0.025 Uiso 1 1 calc R . . . .
H1B H 0.5812 0.3847 0.4437 0.025 Uiso 1 1 calc R . . . .
C1 C 0.8533(4) 0.46461(13) 0.5879(6) 0.0372(10) Uani 1 1 d . . . . .
H1C H 0.947(3) 0.4627(10) 0.568(4) 0.027(9) Uiso 1 1 d . . . . .
H1D H 0.824(4) 0.4833(12) 0.686(6) 0.055(13) Uiso 1 1 d . . . . .
C2 C 0.7660(3) 0.44517(10) 0.4837(4) 0.0258(8) Uani 1 1 d . . . . .
H2 H 0.7974 0.4281 0.3848 0.031 Uiso 1 1 calc R . . . .
C3 C 0.6203(3) 0.44830(10) 0.5110(5) 0.0231(8) Uani 1 1 d . . . . .
H3A H 0.5796 0.4632 0.4058 0.028 Uiso 1 1 calc R . . . .
H3B H 0.6021 0.4676 0.6167 0.028 Uiso 1 1 calc R . . . .
C4 C 0.2411(3) 0.35346(10) 0.4337(4) 0.0218(7) Uani 1 1 d . . . . .
C5 C 0.2998(3) 0.33002(11) 0.6017(4) 0.0217(7) Uani 1 1 d . . . . .
C6 C 0.4064(3) 0.29527(11) 0.5537(4) 0.0271(8) Uani 1 1 d . . . . .
H6A H 0.4677 0.3087 0.4673 0.041 Uiso 1 1 calc GR . . . .
H6B H 0.3649 0.2683 0.5014 0.041 Uiso 1 1 calc GR . . . .
H6C H 0.4548 0.2866 0.6618 0.041 Uiso 1 1 calc GR . . . .
C7 C 0.1995(4) 0.30893(11) 0.7264(5) 0.0292(8) Uani 1 1 d . . . . .
H7A H 0.2453 0.2951 0.8283 0.044 Uiso 1 1 calc GR . . . .
H7B H 0.1495 0.2855 0.6625 0.044 Uiso 1 1 calc GR . . . .
H7C H 0.1388 0.3325 0.7693 0.044 Uiso 1 1 calc GR . . . .
C8 C 0.1136(3) 0.37946(12) 0.4747(5) 0.0289(8) Uani 1 1 d . . . . .
H8A H 0.1259 0.3979 0.5824 0.043 Uiso 1 1 calc GR . . . .
H8B H 0.0414 0.3578 0.4939 0.043 Uiso 1 1 calc GR . . . .
H8C H 0.0917 0.3994 0.3739 0.043 Uiso 1 1 calc GR . . . .
C9 C 0.2189(3) 0.32212(12) 0.2744(4) 0.0284(8) Uani 1 1 d . . . . .
H9A H 0.1838 0.3398 0.1741 0.043 Uiso 1 1 calc GR . . . .
H9B H 0.1556 0.2983 0.3070 0.043 Uiso 1 1 calc GR . . . .
H9C H 0.3029 0.3081 0.2396 0.043 Uiso 1 1 calc GR . . . .
B1 B 0.3994(3) 0.40186(13) 0.5573(5) 0.0218(8) Uani 1 1 d . . . . .
H1 H 0.3644 0.4326 0.5894 0.026 Uiso 1 1 calc R . . . .


_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 C4 1.441(4) . ?
O1 B1 1.463(4) . ?
O2 C5 1.442(4) . ?
O2 B1 1.467(4) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C3 1.493(4) . ?
N1 B1 1.617(4) . ?
C1 H1C 0.96(3) . ?
C1 H1D 0.97(4) . ?
C1 C2 1.310(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.492(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.552(4) . ?
C4 C8 1.531(4) . ?
C4 C9 1.524(4) . ?
C5 C6 1.528(4) . ?
C5 C7 1.512(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
B1 H1 1.0000 . ?

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
C4 O1 B1 106.9(2) . . ?
C5 O2 B1 108.6(2) . . ?
H1A N1 H1B 107.4 . . ?
C3 N1 H1A 108.2 . . ?
C3 N1 H1B 108.2 . . ?
C3 N1 B1 116.3(2) . . ?
B1 N1 H1A 108.2 . . ?
B1 N1 H1B 108.2 . . ?
H1C C1 H1D 117(3) . . ?
C2 C1 H1C 123(2) . . ?
C2 C1 H1D 120(2) . . ?
C1 C2 H2 118.1 . . ?
C1 C2 C3 123.9(3) . . ?
C3 C2 H2 118.1 . . ?
N1 C3 H3A 109.2 . . ?
N1 C3 H3B 109.2 . . ?
C2 C3 N1 112.1(3) . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
O1 C4 C5 102.0(2) . . ?
O1 C4 C8 108.7(2) . . ?
O1 C4 C9 108.7(3) . . ?
C8 C4 C5 112.4(3) . . ?
C9 C4 C5 115.0(2) . . ?
C9 C4 C8 109.5(3) . . ?
O2 C5 C4 101.7(2) . . ?
O2 C5 C6 108.4(3) . . ?
O2 C5 C7 108.7(3) . . ?
C6 C5 C4 112.1(3) . . ?
C7 C5 C4 115.2(3) . . ?
C7 C5 C6 110.2(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 B1 O2 105.6(3) . . ?
O1 B1 N1 108.4(3) . . ?
O1 B1 H1 111.2 . . ?
O2 B1 N1 109.2(2) . . ?
O2 B1 H1 111.2 . . ?
N1 B1 H1 111.2 . . ?

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 C4 C5 O2 38.1(3) . . . . ?
O1 C4 C5 C6 -77.4(3) . . . . ?
O1 C4 C5 C7 155.5(3) . . . . ?
C1 C2 C3 N1 -120.0(4) . . . . ?
C3 N1 B1 O1 103.5(3) . . . . ?
C3 N1 B1 O2 -141.9(3) . . . . ?
C4 O1 B1 O2 18.9(3) . . . . ?
C4 O1 B1 N1 135.8(2) . . . . ?
C5 O2 B1 O1 6.8(3) . . . . ?
C5 O2 B1 N1 -109.5(3) . . . . ?
C8 C4 C5 O2 -78.1(3) . . . . ?
C8 C4 C5 C6 166.3(3) . . . . ?
C8 C4 C5 C7 39.3(4) . . . . ?
C9 C4 C5 O2 155.6(3) . . . . ?
C9 C4 C5 C6 40.1(4) . . . . ?
C9 C4 C5 C7 -87.0(4) . . . . ?
B1 O1 C4 C5 -35.1(3) . . . . ?
B1 O1 C4 C8 83.8(3) . . . . ?
B1 O1 C4 C9 -157.1(3) . . . . ?
B1 O2 C5 C4 -27.4(3) . . . . ?
B1 O2 C5 C6 90.8(3) . . . . ?
B1 O2 C5 C7 -149.4(3) . . . . ?
B1 N1 C3 C2 -176.6(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_original_sample_id AllylNH2HBPin
_olex2_submission_special_instructions 'No special instructions were received'

_chemical_properties_physical    
', Air-sensitive,Moisture-sensitive,Heat-sensitive,Oxygen-sensitive'
