# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_tb055

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H40 B4 N4 O6'
_chemical_formula_weight         379.72

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   16.026(3)
_cell_length_b                   8.7017(15)
_cell_length_c                   17.485(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.469(6)
_cell_angle_gamma                90.00
_cell_volume                     2201.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9894
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      28.28

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9875
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'

_exptl_special_details           
; 
 Data collection is performed with three batch runs at phi = 0.00 deg 
 (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg 
 (650 frames). 
 Frame width = 0.30 deg in omega. 
 Data is merged, corrected for decay (if any), and treated with multi-scan 
 absorption corrections (if required). All symmetry-equivalent reflections 
 are merged for centrosymmetric data. 
 Friedel pairs are not merged for noncentrosymmetric data. 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26868
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.44
_diffrn_reflns_theta_max         24.11
_reflns_number_total             3449
_reflns_number_gt                2709
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0464P)²+1.8748P] 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         3449
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1302
_refine_ls_wR_factor_gt          0.1214
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.69272(18) 0.6759(3) -0.01744(16) 0.0280(6) Uani 1 1 d . . .
H1E H 0.6638 0.7624 0.0002 0.034 Uiso 1 1 calc R . .
B2 B 0.80514(18) 0.5957(3) 0.14028(16) 0.0325(6) Uani 1 1 d . . .
H2E H 0.7841 0.6793 0.1662 0.039 Uiso 1 1 calc R . .
H2F H 0.8234 0.5066 0.1793 0.039 Uiso 1 1 calc R . .
B3 B 0.8656(2) 0.7884(4) 0.05927(19) 0.0441(8) Uani 1 1 d . . .
H3E H 0.9196 0.8135 0.0480 0.053 Uiso 1 1 calc R . .
H3F H 0.8486 0.8808 0.0824 0.053 Uiso 1 1 calc R . .
B4 B 0.5900(2) 0.7310(4) -0.18335(18) 0.0427(7) Uani 1 1 d . . .
H4E H 0.5581 0.6746 -0.2366 0.064 Uiso 1 1 calc R . .
H4F H 0.6435 0.7849 -0.1837 0.064 Uiso 1 1 calc R . .
H4G H 0.5475 0.8058 -0.1773 0.064 Uiso 1 1 calc R . .
N1 N 0.78102(13) 0.7335(2) -0.02532(12) 0.0335(5) Uani 1 1 d . . .
H1C H 0.7641 0.8140 -0.0631 0.040 Uiso 1 1 calc R . .
H1D H 0.8014 0.6554 -0.0485 0.040 Uiso 1 1 calc R . .
N2 N 0.72485(12) 0.5484(2) 0.05108(11) 0.0281(4) Uani 1 1 d . . .
H2C H 0.7447 0.4656 0.0306 0.034 Uiso 1 1 calc R . .
H2D H 0.6747 0.5167 0.0595 0.034 Uiso 1 1 calc R . .
N3 N 0.88909(13) 0.6514(2) 0.12338(12) 0.0354(5) Uani 1 1 d . . .
H3C H 0.9100 0.5701 0.1028 0.042 Uiso 1 1 calc R . .
H3D H 0.9363 0.6809 0.1740 0.042 Uiso 1 1 calc R . .
N4 N 0.62384(14) 0.6132(2) -0.10593(11) 0.0369(5) Uani 1 1 d . . .
H4C H 0.5725 0.5764 -0.1011 0.044 Uiso 1 1 calc R . .
H4D H 0.6513 0.5311 -0.1192 0.044 Uiso 1 1 calc R . .
O1 O 0.19131(11) 0.4965(2) 0.14688(10) 0.0437(5) Uani 1 1 d . . .
O2 O 0.12894(12) 0.65173(19) -0.01433(10) 0.0421(5) Uani 1 1 d . . .
O3 O -0.04164(13) 0.6919(2) -0.15861(11) 0.0476(5) Uani 1 1 d . . .
O4 O 0.59974(11) 0.40593(19) 0.12516(9) 0.0347(4) Uani 1 1 d . . .
O5 O 0.63890(11) 0.24060(19) 0.00064(10) 0.0394(4) Uani 1 1 d . . .
O6 O 0.49326(11) 0.33544(19) -0.15553(10) 0.0405(4) Uani 1 1 d . . .
C1 C 0.1960(2) 0.4082(3) 0.21790(15) 0.0498(7) Uani 1 1 d . . .
H1A H 0.1771 0.4743 0.2538 0.060 Uiso 1 1 calc R . .
H1B H 0.2609 0.3769 0.2522 0.060 Uiso 1 1 calc R . .
C2 C 0.11387(17) 0.5983(3) 0.11274(15) 0.0405(6) Uani 1 1 d . . .
H2A H 0.1045 0.6474 0.1595 0.049 Uiso 1 1 calc R . .
H2B H 0.0574 0.5393 0.0777 0.049 Uiso 1 1 calc R . .
C3 C 0.12964(18) 0.7184(3) 0.06013(16) 0.0429(7) Uani 1 1 d . . .
H3A H 0.0806 0.7975 0.0444 0.052 Uiso 1 1 calc R . .
H3B H 0.1899 0.7690 0.0931 0.052 Uiso 1 1 calc R . .
C4 C 0.11571(19) 0.7611(3) -0.07971(18) 0.0474(7) Uani 1 1 d . . .
H4A H 0.1331 0.7129 -0.1221 0.057 Uiso 1 1 calc R . .
H4B H 0.1575 0.8495 -0.0547 0.057 Uiso 1 1 calc R . .
C5 C 0.01787(19) 0.8190(3) -0.12385(18) 0.0488(7) Uani 1 1 d . . .
H5A H 0.0008 0.8738 -0.0830 0.059 Uiso 1 1 calc R . .
H5B H 0.0122 0.8917 -0.1694 0.059 Uiso 1 1 calc R . .
C6 C -0.13642(19) 0.7325(3) -0.19384(17) 0.0506(7) Uani 1 1 d . . .
H6A H -0.1515 0.7973 -0.2446 0.061 Uiso 1 1 calc R . .
H6B H -0.1491 0.7931 -0.1521 0.061 Uiso 1 1 calc R . .
C7 C 0.62737(17) 0.4773(3) 0.20499(14) 0.0410(6) Uani 1 1 d . . .
H7A H 0.6948 0.4647 0.2387 0.049 Uiso 1 1 calc R . .
H7B H 0.5957 0.4279 0.2362 0.049 Uiso 1 1 calc R . .
C8 C 0.63067(18) 0.2499(3) 0.13340(16) 0.0406(6) Uani 1 1 d . . .
H8A H 0.6083 0.1925 0.1698 0.049 Uiso 1 1 calc R . .
H8B H 0.6991 0.2469 0.1604 0.049 Uiso 1 1 calc R . .
C9 C 0.59485(19) 0.1765(3) 0.04818(17) 0.0453(7) Uani 1 1 d . . .
H9A H 0.6065 0.0645 0.0546 0.054 Uiso 1 1 calc R . .
H9B H 0.5273 0.1928 0.0179 0.054 Uiso 1 1 calc R . .
C10 C 0.61766(18) 0.1666(3) -0.07795(16) 0.0434(7) Uani 1 1 d . . .
H10A H 0.6340 0.0565 -0.0670 0.052 Uiso 1 1 calc R . .
H10B H 0.6567 0.2115 -0.1033 0.052 Uiso 1 1 calc R . .
C11 C 0.51852(19) 0.1787(3) -0.14084(17) 0.0466(7) Uani 1 1 d . . .
H11A H 0.5098 0.1287 -0.1946 0.056 Uiso 1 1 calc R . .
H11B H 0.4787 0.1256 -0.1188 0.056 Uiso 1 1 calc R . .
C12 C 0.39624(17) 0.3564(3) -0.19330(16) 0.0414(7) Uani 1 1 d . . .
H12A H 0.3699 0.3097 -0.1569 0.050 Uiso 1 1 calc R . .
H12B H 0.3688 0.3039 -0.2489 0.050 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
B1 N1 1.562(3) . ?
B1 N2 1.550(3) . ?
B1 N4 1.562(3) . ?
B2 N3 1.573(3) . ?
B2 N2 1.591(3) . ?
B3 N3 1.567(4) . ?
B3 N1 1.591(3) . ?
B4 N4 1.595(3) . ?
O1 C2 1.430(3) . ?
O1 C1 1.434(3) . ?
O2 C3 1.421(3) . ?
O2 C4 1.431(3) . ?
O3 C5 1.415(3) . ?
O3 C6 1.417(3) . ?
O4 C7 1.414(3) . ?
O4 C8 1.431(3) . ?
O5 C9 1.416(3) . ?
O5 C10 1.420(3) . ?
O6 C12 1.416(3) . ?
O6 C11 1.414(3) . ?
C1 C6 1.498(4) 3_565 ?
C2 C3 1.484(4) . ?
C4 C5 1.506(4) . ?
C6 C1 1.498(4) 3_565 ?
C7 C12 1.488(4) 3_665 ?
C8 C9 1.490(4) . ?
C10 C11 1.497(4) . ?
C12 C7 1.488(4) 3_665 ?

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 N2 106.58(18) . . ?
N1 B1 N4 107.80(18) . . ?
N2 B1 N4 111.96(19) . . ?
N3 B2 N2 106.99(18) . . ?
N3 B3 N1 106.5(2) . . ?
B1 N1 B3 117.17(19) . . ?
B1 N2 B2 115.60(18) . . ?
B2 N3 B3 114.03(19) . . ?
B1 N4 B4 116.98(19) . . ?
C2 O1 C1 113.95(19) . . ?
C3 O2 C4 113.62(19) . . ?
C5 O3 C6 113.0(2) . . ?
C7 O4 C8 111.68(18) . . ?
C9 O5 C10 114.63(19) . . ?
C12 O6 C11 112.33(19) . . ?
O1 C1 C6 113.9(2) . 3_565 ?
O1 C2 C3 110.3(2) . . ?
O2 C3 C2 110.1(2) . . ?
O2 C4 C5 113.3(2) . . ?
O3 C5 C4 108.6(2) . . ?
O3 C6 C1 110.7(2) . 3_565 ?
O4 C7 C12 109.8(2) . 3_665 ?
O4 C8 C9 109.7(2) . . ?
O5 C9 C8 110.1(2) . . ?
O5 C10 C11 114.6(2) . . ?
O6 C11 C10 109.4(2) . . ?
O6 C12 C7 110.7(2) . 3_665 ?

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
N2 B1 N1 B3 -54.0(3) . . . . ?
N4 B1 N1 B3 -174.4(2) . . . . ?
N3 B3 N1 B1 55.1(3) . . . . ?
N1 B1 N2 B2 54.5(2) . . . . ?
N4 B1 N2 B2 172.19(19) . . . . ?
N3 B2 N2 B1 -57.3(3) . . . . ?
N2 B2 N3 B3 57.7(3) . . . . ?
N1 B3 N3 B2 -56.0(3) . . . . ?
N1 B1 N4 B4 -59.6(3) . . . . ?
N2 B1 N4 B4 -176.5(2) . . . . ?
C2 O1 C1 C6 82.5(3) . . . 3_565 ?
C1 O1 C2 C3 161.6(2) . . . . ?
C4 O2 C3 C2 162.2(2) . . . . ?
O1 C2 C3 O2 68.3(3) . . . . ?
C3 O2 C4 C5 -74.2(3) . . . . ?
C6 O3 C5 C4 173.7(2) . . . . ?
O2 C4 C5 O3 -58.0(3) . . . . ?
C5 O3 C6 C1 -171.6(2) . . . 3_565 ?
C8 O4 C7 C12 173.2(2) . . . 3_665 ?
C7 O4 C8 C9 176.4(2) . . . . ?
C10 O5 C9 C8 173.1(2) . . . . ?
O4 C8 C9 O5 69.5(3) . . . . ?
C9 O5 C10 C11 64.6(3) . . . . ?
C12 O6 C11 C10 -162.3(2) . . . . ?
O5 C10 C11 O6 56.9(3) . . . . ?
C11 O6 C12 C7 178.1(2) . . . 3_665 ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        24.11
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.041
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Hygroscopic'
_database_code_depnum_ccdc_archive 'CCDC 1022830'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_tb061

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H26 B4 N4 O2'
_chemical_formula_weight         205.53

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'

_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                   6.9419(7)
_cell_length_b                   8.8077(8)
_cell_length_c                   12.4471(12)
_cell_angle_alpha                91.790(3)
_cell_angle_beta                 103.761(3)
_cell_angle_gamma                111.731(3)
_cell_volume                     680.63(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5725
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      28.31

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.003
_exptl_crystal_F_000             228
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.068
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6429
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'

_exptl_special_details           
; 
 Data collection is performed with four batch runs at phi = 0.00 deg 
 (600 frames), at phi = 90.00 deg (600 frames), at phi = 180.00 deg 
 (600 frames), and at phi = 270.00 deg (600 frames). 
 A fifth batch run is collected at phi = 0.00 deg (50 frames) to monitor 
 crystal and diffractometer stability. Frame width = 0.30 deg in omega. 
 Data is merged, corrected for decay (if any), and treated with multi-scan 
 absorption corrections (if required). All symmetry-equivalent reflections 
 are merged for centrosymmetric data. 
 Friedel pairs are not merged for noncentrosymmetric data. 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10580
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.699
_diffrn_reflns_theta_max         28.345
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             3314
_reflns_number_gt                2401
_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       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'

_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)+(0.0847P)²+0.1565P] 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         3314
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1753
_refine_ls_wR_factor_gt          0.1605
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
N1 N 0.28927(19) 0.27272(14) 0.94055(10) 0.0284(3) Uani 1 1 d . . . . .
H1A H 0.4473 0.3148 0.9720 0.034 Uiso 1 1 calc R U . . .
H1B H 0.2225 0.2060 0.9944 0.034 Uiso 1 1 calc R U . . .
N2 N -0.0218(2) 0.09491(16) 0.78267(11) 0.0336(3) Uani 1 1 d . . . . .
H2A H -0.0902 0.0287 0.8362 0.040 Uiso 1 1 calc R U . . .
H2B H -0.0659 0.0210 0.7120 0.040 Uiso 1 1 calc R U . . .
N3 N -0.0285(2) 0.35493(16) 0.87273(11) 0.0341(3) Uani 1 1 d . . . . .
H3A H -0.1042 0.2949 0.9261 0.041 Uiso 1 1 calc R U . . .
H3B H -0.0713 0.4495 0.8587 0.041 Uiso 1 1 calc R U . . .
N4 N 0.29033(19) 0.00555(14) 0.85493(10) 0.0285(3) Uani 1 1 d . . . . .
H4A H 0.4492 0.0474 0.8816 0.034 Uiso 1 1 calc R U . . .
H4B H 0.2468 -0.0662 0.7834 0.034 Uiso 1 1 calc R U . . .
O1 O -0.3165(2) -0.26618(18) 0.64293(12) 0.0582(4) Uani 1 1 d . . . . .
O2 O 0.1067(2) -0.13881(18) 0.61465(10) 0.0548(4) Uani 1 1 d . . . . .
B1 B 0.2277(3) 0.1577(2) 0.82972(14) 0.0281(3) Uani 1 1 d . . . . .
H1C H 0.3016 0.2193 0.7752 0.034 Uiso 1 1 calc R U . . .
B2 B -0.1106(3) 0.2366(3) 0.75989(16) 0.0422(4) Uani 1 1 d . . . . .
H2C H -0.0561 0.2978 0.7008 0.051 Uiso 1 1 calc R U . . .
H2D H -0.2699 0.1889 0.7355 0.051 Uiso 1 1 calc R U . . .
B3 B 0.2204(3) 0.4249(2) 0.93034(15) 0.0324(4) Uani 1 1 d . . . . .
H3C H 0.2525 0.4849 1.0052 0.039 Uiso 1 1 calc R U . . .
H3D H 0.2999 0.5019 0.8849 0.039 Uiso 1 1 calc R U . . .
B4 B 0.1948(3) -0.1068(2) 0.94220(15) 0.0325(4) Uani 1 1 d . . . . .
H4C H 0.2391 -0.0395 1.0147 0.049 Uiso 1 1 calc R U . . .
H4D H 0.2491 -0.1951 0.9499 0.049 Uiso 1 1 calc R U . . .
H4E H 0.0373 -0.1552 0.9158 0.049 Uiso 1 1 calc R U . . .
C1 C -0.4590(4) -0.3314(4) 0.7097(2) 0.0766(7) Uani 1 1 d . . . . .
H1D H -0.5367 -0.2600 0.7158 0.115 Uiso 1 1 calc R U . . .
H1E H -0.3769 -0.3371 0.7842 0.115 Uiso 1 1 calc R U . . .
H1F H -0.5622 -0.4423 0.6753 0.115 Uiso 1 1 calc R U . . .
C2 C -0.2004(4) -0.3644(2) 0.6304(2) 0.0640(6) Uani 1 1 d . . . . .
H2E H -0.3017 -0.4775 0.5963 0.077 Uiso 1 1 calc R U . . .
H2F H -0.1137 -0.3710 0.7044 0.077 Uiso 1 1 calc R U . . .
C3 C -0.0559(4) -0.2902(3) 0.5579(2) 0.0668(6) Uani 1 1 d . . . . .
H3E H 0.0102 -0.3664 0.5397 0.080 Uiso 1 1 calc R U . . .
H3F H -0.1403 -0.2715 0.4872 0.080 Uiso 1 1 calc R U . . .
C4 C 0.2489(4) -0.0591(4) 0.54972(18) 0.0754(8) Uani 1 1 d . . . . .
H4F H 0.3590 0.0445 0.5926 0.113 Uiso 1 1 calc R U . . .
H4G H 0.1674 -0.0358 0.4810 0.113 Uiso 1 1 calc R U . . .
H4H H 0.3183 -0.1311 0.5308 0.113 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 B1 1.557(2) . ?
N1 B3 1.580(2) . ?
N2 B1 1.561(2) . ?
N2 B2 1.590(2) . ?
N3 B2 1.572(2) . ?
N3 B3 1.573(2) . ?
N4 B1 1.574(2) . ?
N4 B4 1.5883(19) . ?
O1 C2 1.410(3) . ?
O1 C1 1.414(3) . ?
O2 C3 1.414(3) . ?
O2 C4 1.422(2) . ?
C2 C3 1.494(3) . ?

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
B1 N1 B3 115.56(12) . . ?
B1 N2 B2 114.60(13) . . ?
B2 N3 B3 116.75(12) . . ?
B1 N4 B4 118.74(11) . . ?
C2 O1 C1 112.15(19) . . ?
C3 O2 C4 112.45(16) . . ?
N1 B1 N2 106.77(11) . . ?
N1 B1 N4 109.47(12) . . ?
N2 B1 N4 108.89(12) . . ?
N3 B2 N2 106.84(13) . . ?
N3 B3 N1 107.17(12) . . ?
O1 C2 C3 109.37(19) . . ?
O2 C3 C2 109.18(17) . . ?

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
B3 N1 B1 N2 -57.87(15) . . . . ?
B3 N1 B1 N4 -175.59(11) . . . . ?
B2 N2 B1 N1 58.46(16) . . . . ?
B2 N2 B1 N4 176.56(12) . . . . ?
B4 N4 B1 N1 56.46(16) . . . . ?
B4 N4 B1 N2 -59.92(16) . . . . ?
B3 N3 B2 N2 53.05(18) . . . . ?
B1 N2 B2 N3 -55.94(18) . . . . ?
B2 N3 B3 N1 -52.18(17) . . . . ?
B1 N1 B3 N3 54.38(15) . . . . ?
C1 O1 C2 C3 179.14(19) . . . . ?
C4 O2 C3 C2 -178.9(2) . . . . ?
O1 C2 C3 O2 67.6(3) . . . . ?

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
N4 H4B O2 0.99 2.06 2.9891(18) 155.3 .
N4 H4A H4C 0.99 2.27 3.181(2) 153.0 2_657
N1 H1A H3C 0.99 2.12 2.998(2) 146.7 2_667
N1 H1B H4E 0.99 2.26 3.117(2) 144.5 2_557
N3 H3A H4D 0.99 2.08 3.067(2) 173.3 2_557

_refine_diff_density_max         0.339
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.049

_shelxl_version_number           2013-4


_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Hygroscopic'
_database_code_depnum_ccdc_archive 'CCDC 1022831'
