# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_2I
_database_code_depnum_ccdc_archive 'CCDC 1035083'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2015-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H29 B I N3'
_chemical_formula_weight         401.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   17.3182(7)
_cell_length_b                   19.7092(5)
_cell_length_c                   12.0924(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 120.773(2)
_cell_angle_gamma                90.00
_cell_volume                     3546.3(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    60769
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      30.50

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1632
_exptl_absorpt_coefficient_mu    1.804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.547
_exptl_absorpt_correction_T_max  0.736
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_special_details           'crystal-to-detector distance 30 mm'
_diffrn_ambient_temperature      150(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  'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method       
'two φ and four ω scans with 2° steps (440 frames)'
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            60769
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         30.50
_reflns_number_total             5407
_reflns_number_gt                4446
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL2000 (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)'

_refine_special_details          
;
 Structure solved by direct methods and subsequent Fourier-difference
 synthesis. All non-hydrogen atoms were refined with anisotropic
 displacement parameters. The H atoms were introduced at calculated
 positions and were treated as riding atoms with an isotropic displacement
 parameter equal to 1.2 times that of the parent atom (1.5 for CH₃). 
 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)+(0.0267P)²+0.6666P] 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         5407
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0596
_refine_ls_wR_factor_gt          0.0572
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.070

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
I1 I 0.368414(8) 0.155746(5) 0.399747(10) 0.03635(5) Uani 1 1 d . . .
N1 N 0.66075(8) 0.10336(6) 0.66629(11) 0.0261(3) Uani 1 1 d . . .
N2 N 0.62998(8) 0.22022(7) 0.66644(12) 0.0275(3) Uani 1 1 d . . .
N3 N 0.63122(9) 0.17123(7) 0.49287(12) 0.0287(3) Uani 1 1 d . . .
B1 B 0.74324(11) 0.09150(9) 0.78395(15) 0.0258(3) Uani 1 1 d . . .
C1 C 0.64030(9) 0.16705(8) 0.60859(13) 0.0251(3) Uani 1 1 d . . .
C2 C 0.59847(12) 0.04918(8) 0.58061(15) 0.0328(3) Uani 1 1 d . . .
H2A H 0.5408 0.0540 0.5748 0.039 Uiso 1 1 calc R . .
H2B H 0.6228 0.0051 0.6178 0.039 Uiso 1 1 calc R . .
C3 C 0.58507(11) 0.05292(9) 0.44510(15) 0.0345(4) Uani 1 1 d . . .
H3A H 0.6003 0.0096 0.4233 0.041 Uiso 1 1 calc R . .
H3B H 0.5225 0.0623 0.3830 0.041 Uiso 1 1 calc R . .
C4 C 0.64366(12) 0.10817(9) 0.43829(15) 0.0335(3) Uani 1 1 d . . .
H4A H 0.7062 0.0945 0.4865 0.040 Uiso 1 1 calc R . .
H4B H 0.6271 0.1156 0.3495 0.040 Uiso 1 1 calc R . .
C5 C 0.60044(12) 0.23391(8) 0.41849(15) 0.0349(4) Uani 1 1 d . . .
H5A H 0.5354 0.2368 0.3746 0.042 Uiso 1 1 calc R . .
H5B H 0.6182 0.2348 0.3543 0.042 Uiso 1 1 calc R . .
C6 C 0.64238(12) 0.29286(8) 0.51020(16) 0.0359(4) Uani 1 1 d . . .
H6A H 0.6203 0.3352 0.4634 0.043 Uiso 1 1 calc R . .
H6B H 0.7071 0.2918 0.5482 0.043 Uiso 1 1 calc R . .
C7 C 0.61966(11) 0.28926(9) 0.61520(16) 0.0344(4) Uani 1 1 d . . .
H7A H 0.6587 0.3198 0.6844 0.041 Uiso 1 1 calc R . .
H7B H 0.5582 0.3042 0.5811 0.041 Uiso 1 1 calc R . .
C8 C 0.62567(12) 0.21507(10) 0.78372(16) 0.0396(4) Uani 1 1 d . . .
H8A H 0.6151 0.1687 0.7967 0.059 Uiso 1 1 calc R . .
H8B H 0.5776 0.2430 0.7756 0.059 Uiso 1 1 calc R . .
H8C H 0.6815 0.2301 0.8559 0.059 Uiso 1 1 calc R . .
C9 C 0.77596(10) 0.02051(8) 0.85023(13) 0.0282(3) Uani 1 1 d . . .
H9 H 0.7255 -0.0115 0.8125 0.034 Uiso 1 1 calc R . .
C10 C 0.84773(12) -0.00273(9) 0.81868(16) 0.0346(4) Uani 1 1 d . . .
H10A H 0.8766 -0.0432 0.8686 0.042 Uiso 1 1 calc R . .
H10B H 0.8175 -0.0153 0.7285 0.042 Uiso 1 1 calc R . .
C11 C 0.92070(11) 0.04938(9) 0.84455(16) 0.0364(4) Uani 1 1 d . . .
H11A H 0.9497 0.0359 0.7974 0.044 Uiso 1 1 calc R . .
H11B H 0.9658 0.0483 0.9355 0.044 Uiso 1 1 calc R . .
C12 C 0.88683(11) 0.12265(9) 0.80720(15) 0.0338(4) Uani 1 1 d . . .
H12A H 0.8583 0.1271 0.7145 0.041 Uiso 1 1 calc R . .
H12B H 0.9383 0.1528 0.8459 0.041 Uiso 1 1 calc R . .
C13 C 0.81947(10) 0.14647(8) 0.84755(14) 0.0278(3) Uani 1 1 d . . .
H13 H 0.7950 0.1909 0.8091 0.033 Uiso 1 1 calc R . .
C14 C 0.85840(12) 0.15010(8) 0.99455(15) 0.0324(3) Uani 1 1 d . . .
H14A H 0.9115 0.1786 1.0320 0.039 Uiso 1 1 calc R . .
H14B H 0.8145 0.1720 1.0098 0.039 Uiso 1 1 calc R . .
C15 C 0.88371(11) 0.08209(9) 1.06487(14) 0.0336(3) Uani 1 1 d . . .
H15A H 0.9397 0.0665 1.0736 0.040 Uiso 1 1 calc R . .
H15B H 0.8937 0.0885 1.1507 0.040 Uiso 1 1 calc R . .
C16 C 0.81215(11) 0.02760(9) 0.99618(14) 0.0337(3) Uani 1 1 d . . .
H16A H 0.7620 0.0375 1.0081 0.040 Uiso 1 1 calc R . .
H16B H 0.8371 -0.0157 1.0371 0.040 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
N1 C1 1.3911(19) . ?
N1 B1 1.428(2) . ?
N1 C2 1.4945(19) . ?
N2 C1 1.322(2) . ?
N2 C8 1.461(2) . ?
N2 C7 1.468(2) . ?
N3 C1 1.3284(18) . ?
N3 C5 1.459(2) . ?
N3 C4 1.474(2) . ?
B1 C9 1.567(2) . ?
B1 C13 1.571(2) . ?
C2 C3 1.535(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.519(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.511(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.511(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.544(2) . ?
C9 C16 1.5478(19) . ?
C9 H9 0.9800 . ?
C10 C11 1.531(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.537(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.550(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.547(2) . ?
C13 H13 0.9800 . ?
C14 C15 1.526(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.525(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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
C1 N1 B1 121.03(12) . . ?
C1 N1 C2 112.88(12) . . ?
B1 N1 C2 124.95(13) . . ?
C1 N2 C8 123.11(14) . . ?
C1 N2 C7 122.13(13) . . ?
C8 N2 C7 114.74(14) . . ?
C1 N3 C5 120.72(13) . . ?
C1 N3 C4 116.99(13) . . ?
C5 N3 C4 121.94(12) . . ?
N1 B1 C9 124.83(14) . . ?
N1 B1 C13 122.44(14) . . ?
C9 B1 C13 111.82(13) . . ?
N2 C1 N3 122.22(14) . . ?
N2 C1 N1 121.25(13) . . ?
N3 C1 N1 116.53(14) . . ?
N1 C2 C3 111.54(13) . . ?
N1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 110.61(13) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
N3 C4 C3 108.99(13) . . ?
N3 C4 H4A 109.9 . . ?
C3 C4 H4A 109.9 . . ?
N3 C4 H4B 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
N3 C5 C6 108.17(13) . . ?
N3 C5 H5A 110.1 . . ?
C6 C5 H5A 110.1 . . ?
N3 C5 H5B 110.1 . . ?
C6 C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?
C5 C6 C7 110.28(14) . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C7 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
N2 C7 C6 111.75(14) . . ?
N2 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
N2 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C16 113.64(13) . . ?
C10 C9 B1 105.34(12) . . ?
C16 C9 B1 109.39(13) . . ?
C10 C9 H9 109.4 . . ?
C16 C9 H9 109.4 . . ?
B1 C9 H9 109.4 . . ?
C11 C10 C9 115.78(13) . . ?
C11 C10 H10A 108.3 . . ?
C9 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
C9 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C10 C11 C12 114.78(14) . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.5 . . ?
C11 C12 C13 115.32(13) . . ?
C11 C12 H12A 108.4 . . ?
C13 C12 H12A 108.4 . . ?
C11 C12 H12B 108.4 . . ?
C13 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
C14 C13 C12 114.84(13) . . ?
C14 C13 B1 110.94(13) . . ?
C12 C13 B1 102.49(12) . . ?
C14 C13 H13 109.4 . . ?
C12 C13 H13 109.4 . . ?
B1 C13 H13 109.4 . . ?
C15 C14 C13 115.57(13) . . ?
C15 C14 H14A 108.4 . . ?
C13 C14 H14A 108.4 . . ?
C15 C14 H14B 108.4 . . ?
C13 C14 H14B 108.4 . . ?
H14A C14 H14B 107.4 . . ?
C16 C15 C14 113.15(13) . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 C9 115.26(13) . . ?
C15 C16 H16A 108.5 . . ?
C9 C16 H16A 108.5 . . ?
C15 C16 H16B 108.5 . . ?
C9 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?



####################################################################### 
# 
# 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_5TBDH
_database_code_depnum_ccdc_archive 'CCDC 1035084'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2015-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H30 B N3 O4'
_chemical_formula_weight         351.25

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   7.1546(4)
_cell_length_b                   12.8526(7)
_cell_length_c                   20.4294(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1878.59(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    42486
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      25.68

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           'crystal-to-detector distance 30 mm'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method       
'two φ and three ω scans with 2° steps (308 frames)'
_diffrn_reflns_number            42486
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.547
_diffrn_reflns_theta_max         25.678
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3552
_reflns_number_gt                3234
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL2000 (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)'

_refine_special_details          
;
 Structure solved by intrinsic phasing. One C atom of the TBD molecule
 is disordered over two positions which were refined with occupancies
 constrained to sum to unity. All non-hydrogen atoms were refined with
 anisotropic displacement parameters, with restraints for two bond lengths
 in the disordered part:
DFIX 1.52 0.01 C15 C16B
DFIX 1.52 0.01 C16B C17
 The H atoms bound to N atoms were found on a difference Fourier map
 and all the others were introduced at calculated positions; all were treated
 as riding atoms with an isotropic displacement parameter equal to 1.2
 times that of the parent atom. 
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0433P)²+0.2454P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3552
_refine_ls_number_parameters     237
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0882
_refine_ls_wR_factor_gt          0.0856
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.068
_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
O1 O 0.9197(2) 0.50797(12) 0.54621(7) 0.0397(4) Uani 1 1 d . . . . .
O2 O 0.6733(2) 0.55259(13) 0.48711(9) 0.0504(5) Uani 1 1 d . . . . .
O3 O 0.9671(2) 0.33144(12) 0.58862(7) 0.0382(4) Uani 1 1 d . . . . .
O4 O 1.0463(3) 0.18843(15) 0.53600(10) 0.0670(6) Uani 1 1 d . . . . .
N1 N 0.3254(3) 0.55630(14) 0.42423(9) 0.0405(5) Uani 1 1 d . . . . .
H1 H 0.4323 0.5315 0.4467 0.049 Uiso 1 1 d R U . . .
N2 N 0.2248(3) 0.39270(15) 0.39699(10) 0.0450(5) Uani 1 1 d . . . . .
H2 H 0.3393 0.3697 0.4155 0.054 Uiso 1 1 d R U . . .
N3 N 0.0350(3) 0.53506(14) 0.37611(9) 0.0375(4) Uani 1 1 d . . . . .
B1 B 0.9992(3) 0.44747(19) 0.60426(12) 0.0329(5) Uani 1 1 d . . . . .
C1 C 0.7452(3) 0.50099(18) 0.53028(12) 0.0409(5) Uani 1 1 d . . . . .
H1A H 0.6691 0.4530 0.5535 0.049 Uiso 1 1 calc R U . . .
C2 C 1.0697(4) 0.28001(19) 0.54882(12) 0.0496(6) Uani 1 1 d . . . . .
H2A H 1.1700 0.3154 0.5280 0.060 Uiso 1 1 calc R U . . .
C3 C 1.2140(3) 0.47996(17) 0.61290(10) 0.0363(5) Uani 1 1 d . . . . .
H3 H 1.2811 0.4662 0.5708 0.044 Uiso 1 1 calc R U . . .
C4 C 1.3017(3) 0.4121(2) 0.66683(12) 0.0455(6) Uani 1 1 d . . . . .
H4A H 1.3129 0.3401 0.6501 0.055 Uiso 1 1 calc R U . . .
H4B H 1.4298 0.4379 0.6754 0.055 Uiso 1 1 calc R U . . .
C5 C 1.1960(4) 0.4089(2) 0.73154(12) 0.0508(6) Uani 1 1 d . . . . .
H5A H 1.2258 0.4727 0.7565 0.061 Uiso 1 1 calc R U . . .
H5B H 1.2419 0.3488 0.7573 0.061 Uiso 1 1 calc R U . . .
C6 C 0.9837(4) 0.4002(2) 0.72514(11) 0.0465(6) Uani 1 1 d . . . . .
H6A H 0.9267 0.4174 0.7679 0.056 Uiso 1 1 calc R U . . .
H6B H 0.9516 0.3270 0.7151 0.056 Uiso 1 1 calc R U . . .
C7 C 0.8957(3) 0.47048(18) 0.67249(11) 0.0390(5) Uani 1 1 d . . . . .
H7 H 0.7611 0.4510 0.6678 0.047 Uiso 1 1 calc R U . . .
C8 C 0.9072(4) 0.58825(19) 0.68685(13) 0.0492(6) Uani 1 1 d . . . . .
H8A H 0.8288 0.6255 0.6545 0.059 Uiso 1 1 calc R U . . .
H8B H 0.8533 0.6013 0.7307 0.059 Uiso 1 1 calc R U . . .
C9 C 1.1035(4) 0.63398(19) 0.68489(13) 0.0505(6) Uani 1 1 d . . . . .
H9A H 1.1682 0.6159 0.7262 0.061 Uiso 1 1 calc R U . . .
H9B H 1.0934 0.7107 0.6830 0.061 Uiso 1 1 calc R U . . .
C10 C 1.2237(3) 0.59742(18) 0.62759(12) 0.0438(6) Uani 1 1 d . . . . .
H10A H 1.3554 0.6161 0.6367 0.053 Uiso 1 1 calc R U . . .
H10B H 1.1849 0.6359 0.5879 0.053 Uiso 1 1 calc R U . . .
C11 C 0.1935(3) 0.49503(17) 0.39953(10) 0.0343(5) Uani 1 1 d . . . . .
C12 C 0.3060(4) 0.66831(19) 0.42653(13) 0.0494(6) Uani 1 1 d . . . . .
H12A H 0.3535 0.6992 0.3854 0.059 Uiso 1 1 calc R U . . .
H12B H 0.3804 0.6966 0.4633 0.059 Uiso 1 1 calc R U . . .
C13 C 0.1037(4) 0.69609(18) 0.43547(12) 0.0470(6) Uani 1 1 d . . . . .
H13A H 0.0884 0.7726 0.4335 0.056 Uiso 1 1 calc R U . . .
H13B H 0.0602 0.6720 0.4789 0.056 Uiso 1 1 calc R U . . .
C14 C -0.0115(4) 0.64584(18) 0.38261(11) 0.0429(6) Uani 1 1 d . . . . .
H14A H -0.1458 0.6532 0.3932 0.052 Uiso 1 1 calc R U . . .
H14B H 0.0118 0.6816 0.3405 0.052 Uiso 1 1 calc R U . . .
C15 C -0.1055(4) 0.4712(2) 0.34362(13) 0.0507(6) Uani 1 1 d D . . . .
H15A H -0.1528 0.5085 0.3047 0.061 Uiso 0.857(7) 1 d R U P . .
H15B H -0.2111 0.4598 0.3739 0.061 Uiso 0.857(7) 1 d R U P . .
H15C H -0.2297 0.5024 0.3503 0.061 Uiso 0.143(7) 1 d R U P . .
H15D H -0.0801 0.4694 0.2959 0.061 Uiso 0.143(7) 1 d R U P . .
C16A C -0.0269(5) 0.3670(2) 0.32124(16) 0.0502(11) Uani 0.857(7) 1 d . . P . .
H16A H -0.1305 0.3200 0.3095 0.060 Uiso 0.857(7) 1 d R U P . .
H16B H 0.0513 0.3765 0.2818 0.060 Uiso 0.857(7) 1 d R U P . .
C16B C -0.1070(18) 0.3663(10) 0.3713(9) 0.051(6) Uani 0.143(7) 1 d D . P . .
H16C H -0.1864 0.3228 0.3427 0.061 Uiso 0.143(7) 1 d R U P . .
H16D H -0.1653 0.3676 0.4152 0.061 Uiso 0.143(7) 1 d R U P . .
C17 C 0.0851(4) 0.3190(2) 0.37372(14) 0.0569(7) Uani 1 1 d D . . . .
H17A H 0.1456 0.2553 0.3572 0.068 Uiso 0.857(7) 1 d R U P . .
H17B H 0.0037 0.2998 0.4109 0.068 Uiso 0.857(7) 1 d R U P . .
H17C H 0.0761 0.2605 0.4050 0.068 Uiso 0.143(7) 1 d R U P . .
H17D H 0.1226 0.2908 0.3306 0.068 Uiso 0.143(7) 1 d 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
O1 C1 1.293(3) . ?
O1 B1 1.528(3) . ?
O2 C1 1.218(3) . ?
O3 C2 1.279(3) . ?
O3 B1 1.542(3) . ?
O4 C2 1.217(3) . ?
N1 C11 1.329(3) . ?
N1 C12 1.447(3) . ?
N1 H1 0.9472 . ?
N2 C11 1.335(3) . ?
N2 C17 1.456(3) . ?
N2 H2 0.9493 . ?
N3 C11 1.334(3) . ?
N3 C15 1.458(3) . ?
N3 C14 1.468(3) . ?
B1 C3 1.603(3) . ?
B1 C7 1.606(3) . ?
C1 H1A 0.9500 . ?
C2 H2A 0.9500 . ?
C3 C4 1.539(3) . ?
C3 C10 1.541(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.523(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.529(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.539(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.544(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.523(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.527(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C12 C13 1.502(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.504(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16B 1.462(11) . ?
C15 C16A 1.522(4) . ?
C15 H15A 0.9893 . ?
C15 H15B 0.9868 . ?
C15 H15C 0.9843 . ?
C15 H15D 0.9909 . ?
C16A C17 1.474(4) . ?
C16A H16A 0.9852 . ?
C16A H16B 0.9889 . ?
C16B C17 1.503(11) . ?
C16B H16C 0.9873 . ?
C16B H16D 0.9901 . ?
C17 H17A 0.9864 . ?
C17 H17B 0.9883 . ?
C17 H17C 0.9885 . ?
C17 H17D 0.9902 . ?

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
C1 O1 B1 121.28(18) . . ?
C2 O3 B1 123.11(18) . . ?
C11 N1 C12 122.3(2) . . ?
C11 N1 H1 123.9 . . ?
C12 N1 H1 113.4 . . ?
C11 N2 C17 122.6(2) . . ?
C11 N2 H2 115.9 . . ?
C17 N2 H2 121.3 . . ?
C11 N3 C15 122.15(19) . . ?
C11 N3 C14 122.28(19) . . ?
C15 N3 C14 115.55(19) . . ?
O1 B1 O3 106.03(16) . . ?
O1 B1 C3 108.04(17) . . ?
O3 B1 C3 114.66(18) . . ?
O1 B1 C7 114.12(18) . . ?
O3 B1 C7 106.83(17) . . ?
C3 B1 C7 107.36(18) . . ?
O2 C1 O1 123.5(2) . . ?
O2 C1 H1A 118.2 . . ?
O1 C1 H1A 118.2 . . ?
O4 C2 O3 123.9(2) . . ?
O4 C2 H2A 118.1 . . ?
O3 C2 H2A 118.1 . . ?
C4 C3 C10 113.41(19) . . ?
C4 C3 B1 108.80(19) . . ?
C10 C3 B1 108.66(18) . . ?
C4 C3 H3 108.6 . . ?
C10 C3 H3 108.6 . . ?
B1 C3 H3 108.6 . . ?
C5 C4 C3 115.8(2) . . ?
C5 C4 H4A 108.3 . . ?
C3 C4 H4A 108.3 . . ?
C5 C4 H4B 108.3 . . ?
C3 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?
C4 C5 C6 114.9(2) . . ?
C4 C5 H5A 108.5 . . ?
C6 C5 H5A 108.5 . . ?
C4 C5 H5B 108.5 . . ?
C6 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C5 C6 C7 115.0(2) . . ?
C5 C6 H6A 108.5 . . ?
C7 C6 H6A 108.5 . . ?
C5 C6 H6B 108.5 . . ?
C7 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
C6 C7 C8 114.9(2) . . ?
C6 C7 B1 108.07(18) . . ?
C8 C7 B1 108.73(18) . . ?
C6 C7 H7 108.3 . . ?
C8 C7 H7 108.3 . . ?
B1 C7 H7 108.3 . . ?
C9 C8 C7 115.0(2) . . ?
C9 C8 H8A 108.5 . . ?
C7 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C8 C9 C10 114.9(2) . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9B 108.5 . . ?
C10 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C9 C10 C3 115.2(2) . . ?
C9 C10 H10A 108.5 . . ?
C3 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
C3 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
N1 C11 N3 120.8(2) . . ?
N1 C11 N2 118.7(2) . . ?
N3 C11 N2 120.5(2) . . ?
N1 C12 C13 109.4(2) . . ?
N1 C12 H12A 109.8 . . ?
C13 C12 H12A 109.8 . . ?
N1 C12 H12B 109.8 . . ?
C13 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
C12 C13 C14 109.8(2) . . ?
C12 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
C12 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
N3 C14 C13 110.94(19) . . ?
N3 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.0 . . ?
N3 C15 C16B 110.4(7) . . ?
N3 C15 C16A 112.2(2) . . ?
N3 C15 H15A 109.2 . . ?
C16A C15 H15A 108.2 . . ?
N3 C15 H15B 109.1 . . ?
C16A C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
N3 C15 H15C 109.3 . . ?
C16B C15 H15C 108.4 . . ?
N3 C15 H15D 109.5 . . ?
C16B C15 H15D 111.1 . . ?
H15C C15 H15D 108.1 . . ?
C17 C16A C15 110.5(2) . . ?
C17 C16A H16A 109.2 . . ?
C15 C16A H16A 109.5 . . ?
C17 C16A H16B 109.7 . . ?
C15 C16A H16B 110.2 . . ?
H16A C16A H16B 107.7 . . ?
C15 C16B C17 112.3(9) . . ?
C15 C16B H16C 107.3 . . ?
C17 C16B H16C 108.5 . . ?
C15 C16B H16D 109.8 . . ?
C17 C16B H16D 111.2 . . ?
H16C C16B H16D 107.6 . . ?
N2 C17 C16A 109.8(2) . . ?
N2 C17 C16B 112.0(6) . . ?
N2 C17 H17A 110.5 . . ?
C16A C17 H17A 109.7 . . ?
N2 C17 H17B 108.4 . . ?
C16A C17 H17B 110.1 . . ?
H17A C17 H17B 108.3 . . ?
N2 C17 H17C 109.2 . . ?
C16B C17 H17C 105.6 . . ?
N2 C17 H17D 110.0 . . ?
C16B C17 H17D 111.5 . . ?
H17C C17 H17D 108.3 . . ?

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
N1 H1 O2 0.95 1.93 2.801(2) 151.8 .
N2 H2 O4 0.95 1.93 2.873(3) 170.4 4_456

_refine_diff_density_max         0.162
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.028

_shelxl_version_number           2014-3




