# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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. 
# 
#######################################################################

data_schm117
_database_code_depnum_ccdc_archive 'CCDC 1845098'
_audit_update_record             
;
2018-05-24 deposited with the CCDC.
2018-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
7,7-diethyl-8-methyl-7,8-dihydroimidazo[2',1':3,4][1,4,2]-diazaborinino[1,6,5-gh]purin-11-ium-7-uide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H17 B N6'
_chemical_formula_sum            'C13 H17 B N6'
_chemical_formula_weight         268.13

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.2834(4)
_cell_length_b                   7.5733(4)
_cell_length_c                   12.2004(7)
_cell_angle_alpha                92.486(2)
_cell_angle_beta                 94.926(2)
_cell_angle_gamma                96.678(2)
_cell_volume                     664.96(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9021
_cell_measurement_theta_min      7.7
_cell_measurement_theta_max      72.1

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.680
_shelx_estimated_absorpt_T_min   0.792
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8047
_exptl_absorpt_correction_T_max  0.9288
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 dx = 40 mm, 1 deg., 15+1 runs, 2452 frames, 4/6/8/10 sec./frame
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE with Photon100 detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            10331
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         6.762
_diffrn_reflns_theta_max         72.158
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2589
_reflns_number_gt                2467
_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       APEX3
_computing_cell_refinement       APEX3
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Shelxtl
_computing_publication_material  publCIF

_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)+(0.0469P)²+0.2862P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_extinction_coef       0.017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2589
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0952
_refine_ls_wR_factor_gt          0.0938
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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_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
B1 B 0.43903(17) 0.25097(16) 0.19830(10) 0.0156(3) Uani 1 1 d . . . . .
N1 N 0.55445(13) 0.42879(12) 0.25545(8) 0.0163(2) Uani 1 1 d . . . . .
C2 C 0.71154(16) 0.53629(15) 0.23904(10) 0.0220(3) Uani 1 1 d . . . . .
H2 H 0.7950 0.5031 0.1883 0.026 Uiso 1 1 calc R U . . .
N3 N 0.74180(14) 0.69091(13) 0.29816(9) 0.0233(2) Uani 1 1 d . . . . .
C3A C 0.59046(15) 0.68670(15) 0.35762(9) 0.0174(2) Uani 1 1 d . . . . .
N4 N 0.54566(14) 0.80978(13) 0.43120(8) 0.0199(2) Uani 1 1 d . . . . .
C5 C 0.38587(17) 0.76212(15) 0.47360(10) 0.0195(3) Uani 1 1 d . . . . .
H5 H 0.3491 0.8471 0.5243 0.023 Uiso 1 1 calc R U . . .
N6 N 0.26764(13) 0.60845(12) 0.45449(8) 0.0183(2) Uani 1 1 d . . . . .
C7 C 0.31827(15) 0.49111(14) 0.38276(9) 0.0148(2) Uani 1 1 d . . . . .
C7A C 0.47740(15) 0.52700(14) 0.33127(9) 0.0154(2) Uani 1 1 d . . . . .
N8 N 0.21549(12) 0.32283(12) 0.35725(7) 0.0148(2) Uani 1 1 d . . . . .
C9 C 0.06374(15) 0.24610(15) 0.40688(9) 0.0183(3) Uani 1 1 d . . . . .
H9 H 0.0001 0.2999 0.4618 0.022 Uiso 1 1 calc R U . . .
C10 C 0.02542(16) 0.07994(15) 0.36119(9) 0.0191(3) Uani 1 1 d . . . . .
H10 H -0.0718 -0.0069 0.3777 0.023 Uiso 1 1 calc R U . . .
N11 N 0.15404(13) 0.05816(12) 0.28522(8) 0.0163(2) Uani 1 1 d . . . . .
C11 C 0.15222(17) -0.10826(15) 0.21876(10) 0.0218(3) Uani 1 1 d . . . . .
H11A H 0.1577 -0.0819 0.1411 0.033 Uiso 1 1 calc R U . . .
H11B H 0.0379 -0.1866 0.2272 0.033 Uiso 1 1 calc R U . . .
H11C H 0.2598 -0.1675 0.2436 0.033 Uiso 1 1 calc R U . . .
C12 C 0.27300(15) 0.20635(14) 0.28213(9) 0.0146(2) Uani 1 1 d . . . . .
C13 C 0.56730(16) 0.09056(15) 0.18867(10) 0.0207(3) Uani 1 1 d . . . . .
H13A H 0.6095 0.0600 0.2640 0.025 Uiso 1 1 calc R U . . .
H13B H 0.4893 -0.0155 0.1528 0.025 Uiso 1 1 calc R U . . .
C14 C 0.73799(17) 0.12895(17) 0.12473(11) 0.0256(3) Uani 1 1 d . . . . .
H14A H 0.8058 0.0245 0.1236 0.038 Uiso 1 1 calc R U . . .
H14B H 0.6985 0.1556 0.0490 0.038 Uiso 1 1 calc R U . . .
H14C H 0.8190 0.2313 0.1606 0.038 Uiso 1 1 calc R U . . .
C15 C 0.33808(17) 0.29943(16) 0.08068(9) 0.0214(3) Uani 1 1 d . . . . .
H15A H 0.4340 0.3198 0.0283 0.026 Uiso 1 1 calc R U . . .
H15B H 0.2507 0.1949 0.0512 0.026 Uiso 1 1 calc R U . . .
C16 C 0.23171(18) 0.46173(19) 0.08433(11) 0.0287(3) Uani 1 1 d . . . . .
H16A H 0.1764 0.4798 0.0102 0.043 Uiso 1 1 calc R U . . .
H16B H 0.1334 0.4421 0.1340 0.043 Uiso 1 1 calc R U . . .
H16C H 0.3171 0.5673 0.1111 0.043 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
B1 N1 1.6003(14) . ?
B1 C13 1.6226(16) . ?
B1 C15 1.6315(17) . ?
B1 C12 1.6643(16) . ?
N1 C2 1.3597(15) . ?
N1 C7A 1.3603(14) . ?
C2 N3 1.3339(15) . ?
C2 H2 0.9500 . ?
N3 C3A 1.3688(15) . ?
C3A N4 1.3527(15) . ?
C3A C7A 1.3905(15) . ?
N4 C5 1.3320(15) . ?
C5 N6 1.3635(15) . ?
C5 H5 0.9500 . ?
N6 C7 1.3251(14) . ?
C7 C7A 1.3705(16) . ?
C7 N8 1.4090(14) . ?
N8 C12 1.3694(14) . ?
N8 C9 1.3863(14) . ?
C9 C10 1.3427(16) . ?
C9 H9 0.9500 . ?
C10 N11 1.3913(14) . ?
C10 H10 0.9500 . ?
N11 C12 1.3397(14) . ?
N11 C11 1.4669(14) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 C14 1.5300(16) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.5283(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
N1 B1 C13 111.79(9) . . ?
N1 B1 C15 108.41(9) . . ?
C13 B1 C15 113.93(9) . . ?
N1 B1 C12 102.73(8) . . ?
C13 B1 C12 112.09(9) . . ?
C15 B1 C12 107.17(9) . . ?
C2 N1 C7A 102.31(9) . . ?
C2 N1 B1 137.06(10) . . ?
C7A N1 B1 119.75(9) . . ?
N3 C2 N1 116.25(10) . . ?
N3 C2 H2 121.9 . . ?
N1 C2 H2 121.9 . . ?
C2 N3 C3A 103.06(9) . . ?
N4 C3A N3 129.46(10) . . ?
N4 C3A C7A 121.74(10) . . ?
N3 C3A C7A 108.80(10) . . ?
C5 N4 C3A 113.46(10) . . ?
N4 C5 N6 129.10(11) . . ?
N4 C5 H5 115.4 . . ?
N6 C5 H5 115.4 . . ?
C7 N6 C5 115.26(10) . . ?
N6 C7 C7A 121.06(10) . . ?
N6 C7 N8 122.36(10) . . ?
C7A C7 N8 116.57(10) . . ?
N1 C7A C7 131.07(10) . . ?
N1 C7A C3A 109.57(10) . . ?
C7 C7A C3A 119.34(10) . . ?
C12 N8 C9 111.61(9) . . ?
C12 N8 C7 120.21(9) . . ?
C9 N8 C7 127.91(9) . . ?
C10 C9 N8 105.66(10) . . ?
C10 C9 H9 127.2 . . ?
N8 C9 H9 127.2 . . ?
C9 C10 N11 107.52(10) . . ?
C9 C10 H10 126.2 . . ?
N11 C10 H10 126.2 . . ?
C12 N11 C10 111.15(9) . . ?
C12 N11 C11 126.51(9) . . ?
C10 N11 C11 122.34(9) . . ?
N11 C11 H11A 109.5 . . ?
N11 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N11 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N11 C12 N8 104.06(9) . . ?
N11 C12 B1 129.02(9) . . ?
N8 C12 B1 126.63(9) . . ?
C14 C13 B1 115.77(10) . . ?
C14 C13 H13A 108.3 . . ?
B1 C13 H13A 108.3 . . ?
C14 C13 H13B 108.3 . . ?
B1 C13 H13B 108.3 . . ?
H13A C13 H13B 107.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 B1 115.62(10) . . ?
C16 C15 H15A 108.4 . . ?
B1 C15 H15A 108.4 . . ?
C16 C15 H15B 108.4 . . ?
B1 C15 H15B 108.4 . . ?
H15A C15 H15B 107.4 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
C13 B1 N1 C2 55.16(17) . . . . ?
C15 B1 N1 C2 -71.25(16) . . . . ?
C12 B1 N1 C2 175.53(12) . . . . ?
C13 B1 N1 C7A -137.76(10) . . . . ?
C15 B1 N1 C7A 95.83(11) . . . . ?
C12 B1 N1 C7A -17.39(12) . . . . ?
C7A N1 C2 N3 0.90(14) . . . . ?
B1 N1 C2 N3 169.44(12) . . . . ?
N1 C2 N3 C3A -0.94(14) . . . . ?
C2 N3 C3A N4 -179.32(12) . . . . ?
C2 N3 C3A C7A 0.57(13) . . . . ?
N3 C3A N4 C5 179.61(12) . . . . ?
C7A C3A N4 C5 -0.26(16) . . . . ?
C3A N4 C5 N6 1.46(18) . . . . ?
N4 C5 N6 C7 -0.79(18) . . . . ?
C5 N6 C7 C7A -1.12(16) . . . . ?
C5 N6 C7 N8 177.35(10) . . . . ?
C2 N1 C7A C7 -178.99(12) . . . . ?
B1 N1 C7A C7 9.97(18) . . . . ?
C2 N1 C7A C3A -0.45(12) . . . . ?
B1 N1 C7A C3A -171.49(9) . . . . ?
N6 C7 C7A N1 -179.41(11) . . . . ?
N8 C7 C7A N1 2.03(18) . . . . ?
N6 C7 C7A C3A 2.17(17) . . . . ?
N8 C7 C7A C3A -176.39(10) . . . . ?
N4 C3A C7A N1 179.83(10) . . . . ?
N3 C3A C7A N1 -0.07(13) . . . . ?
N4 C3A C7A C7 -1.43(17) . . . . ?
N3 C3A C7A C7 178.67(10) . . . . ?
N6 C7 N8 C12 179.70(10) . . . . ?
C7A C7 N8 C12 -1.76(15) . . . . ?
N6 C7 N8 C9 -6.83(18) . . . . ?
C7A C7 N8 C9 171.71(10) . . . . ?
C12 N8 C9 C10 -0.53(13) . . . . ?
C7 N8 C9 C10 -174.46(11) . . . . ?
N8 C9 C10 N11 0.19(13) . . . . ?
C9 C10 N11 C12 0.21(13) . . . . ?
C9 C10 N11 C11 -179.40(10) . . . . ?
C10 N11 C12 N8 -0.52(12) . . . . ?
C11 N11 C12 N8 179.08(10) . . . . ?
C10 N11 C12 B1 -174.56(10) . . . . ?
C11 N11 C12 B1 5.03(18) . . . . ?
C9 N8 C12 N11 0.64(12) . . . . ?
C7 N8 C12 N11 175.10(9) . . . . ?
C9 N8 C12 B1 174.88(10) . . . . ?
C7 N8 C12 B1 -10.66(16) . . . . ?
N1 B1 C12 N11 -168.10(10) . . . . ?
C13 B1 C12 N11 -47.93(15) . . . . ?
C15 B1 C12 N11 77.78(13) . . . . ?
N1 B1 C12 N8 19.10(14) . . . . ?
C13 B1 C12 N8 139.26(11) . . . . ?
C15 B1 C12 N8 -95.03(12) . . . . ?
N1 B1 C13 C14 -58.05(13) . . . . ?
C15 B1 C13 C14 65.29(13) . . . . ?
C12 B1 C13 C14 -172.79(10) . . . . ?
N1 B1 C15 C16 -48.97(13) . . . . ?
C13 B1 C15 C16 -174.13(10) . . . . ?
C12 B1 C15 C16 61.28(12) . . . . ?

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
C5 H5 N4 0.95 2.64 3.3625(15) 133.1 2_676
C9 H9 N6 0.95 2.43 3.3252(15) 156.1 2_566
C10 H10 N3 0.95 2.62 3.4138(15) 141.0 1_445
C11 H11B N3 0.98 2.49 3.4286(15) 160.9 1_445

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.039

