# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_jhbu1016d
_database_code_depnum_ccdc_archive 'CCDC 1518084'
_audit_update_record             
;
2016-11-20 deposited with the CCDC.
2017-08-08 downloaded from the CCDC.
;
_audit_creation_date             2016-10-19
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.10.10 svn.r3347 for OlexSys, GUI svn.r5252)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        'glyzide diazaborine'
_chemical_formula_moiety         'C9 H10 B N3 O2'
_chemical_formula_sum            'C9 H10 B N3 O2'
_chemical_formula_weight         203.01
_chemical_absolute_configuration unk
_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 0.0181 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'

_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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   17.2080(8)
_cell_length_b                   5.9717(2)
_cell_length_c                   9.2902(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     954.67(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2420
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.14
_cell_measurement_theta_min      5.14
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.907
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1182 before and 0.0848 after correction. The Ratio of minimum to maximum transmission is 0.7106. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.041
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0908
_diffrn_reflns_av_unetI/netI     0.0917
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5191
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.136
_diffrn_reflns_theta_min         5.140
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                1512
_reflns_number_total             1738
_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       'COSMO (BRUKER, V1.61, 2009)'
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.112
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.1(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1738
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0747
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1049P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1696
_refine_ls_wR_factor_ref         0.1781
_refine_special_details          
'The structure was refined by Least Squares using version 2014/6 of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). All non-hydrogen atoms were refined anisotropically. Hydrogen atom positions were calculated geometrically and refined using the riding model.'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.1(7) -0.1(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C1(H1C,H1D)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9)
;
_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 0.2982(2) -0.0307(6) 0.9565(4) 0.0183(8) Uani 1 1 d . . . . .
O2 O 0.1716(2) 0.5946(6) 0.8568(5) 0.0284(9) Uani 1 1 d . . . . .
N1 N 0.2082(2) 0.0283(7) 0.7503(4) 0.0179(9) Uani 1 1 d . . . . .
H1A H 0.2137 0.0184 0.6531 0.021 Uiso 1 1 calc R . . . .
H1B H 0.1910 -0.1060 0.7840 0.021 Uiso 1 1 calc R . . . .
N2 N 0.2736(2) 0.3406(7) 0.8528(5) 0.0194(9) Uani 1 1 d . . . . .
N3 N 0.3308(3) 0.5010(7) 0.8842(5) 0.0245(10) Uani 1 1 d . . . . .
C1 C 0.1518(3) 0.2088(8) 0.7876(6) 0.0211(10) Uani 1 1 d . . . . .
H1C H 0.1163 0.1580 0.8648 0.025 Uiso 1 1 calc R . . . .
H1D H 0.1204 0.2501 0.7023 0.025 Uiso 1 1 calc R . . . .
C2 C 0.1996(3) 0.4072(8) 0.8383(6) 0.0203(10) Uani 1 1 d . . . . .
C3 C 0.3988(3) 0.4469(8) 0.8346(6) 0.0255(12) Uani 1 1 d . . . . .
H3 H 0.4404 0.5431 0.8610 0.031 Uiso 1 1 calc R . . . .
C4 C 0.4193(3) 0.2572(9) 0.7436(6) 0.0223(10) Uani 1 1 d . . . . .
C5 C 0.3652(3) 0.0787(8) 0.7217(5) 0.0186(10) Uani 1 1 d . . . . .
C6 C 0.3854(3) -0.0914(10) 0.6276(5) 0.0228(11) Uani 1 1 d . . . . .
H6 H 0.3498 -0.2102 0.6110 0.027 Uiso 1 1 calc R . . . .
C7 C 0.4566(3) -0.0926(10) 0.5570(6) 0.0278(12) Uani 1 1 d . . . . .
H7 H 0.4691 -0.2107 0.4925 0.033 Uiso 1 1 calc R . . . .
C8 C 0.5098(3) 0.0801(11) 0.5810(7) 0.0330(13) Uani 1 1 d . . . . .
H8 H 0.5588 0.0780 0.5340 0.040 Uiso 1 1 calc R . . . .
C9 C 0.4914(3) 0.2534(10) 0.6727(7) 0.0299(12) Uani 1 1 d . . . . .
H9 H 0.5277 0.3710 0.6881 0.036 Uiso 1 1 calc R . . . .
B1 B 0.2901(3) 0.0916(9) 0.8238(5) 0.0159(10) Uani 1 1 d . . . . .
H1 H 0.306(5) -0.161(16) 0.945(8) 0.033(19) Uiso 1 1 d . . . . .


_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 B1 1.439(7) . ?
O1 H1 0.80(9) . ?
O2 C2 1.231(6) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C1 1.491(6) . ?
N1 B1 1.611(6) . ?
N2 N3 1.404(6) . ?
N2 C2 1.340(7) . ?
N2 B1 1.538(6) . ?
N3 C3 1.298(8) . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?
C1 C2 1.518(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.457(8) . ?
C4 C5 1.429(7) . ?
C4 C9 1.406(8) . ?
C5 C6 1.385(8) . ?
C5 B1 1.605(7) . ?
C6 H6 0.9500 . ?
C6 C7 1.390(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.397(9) . ?
C8 H8 0.9500 . ?
C8 C9 1.377(10) . ?
C9 H9 0.9500 . ?

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 O1 H1 113(6) . . ?
H1A N1 H1B 108.5 . . ?
C1 N1 H1A 110.2 . . ?
C1 N1 H1B 110.2 . . ?
C1 N1 B1 107.5(4) . . ?
B1 N1 H1A 110.2 . . ?
B1 N1 H1B 110.2 . . ?
N3 N2 B1 124.5(4) . . ?
C2 N2 N3 118.9(4) . . ?
C2 N2 B1 116.4(4) . . ?
C3 N3 N2 112.9(4) . . ?
N1 C1 H1C 110.4 . . ?
N1 C1 H1D 110.4 . . ?
N1 C1 C2 106.5(4) . . ?
H1C C1 H1D 108.6 . . ?
C2 C1 H1C 110.4 . . ?
C2 C1 H1D 110.4 . . ?
O2 C2 N2 128.9(5) . . ?
O2 C2 C1 122.7(5) . . ?
N2 C2 C1 108.3(4) . . ?
N3 C3 H3 115.9 . . ?
N3 C3 C4 128.1(5) . . ?
C4 C3 H3 115.9 . . ?
C5 C4 C3 120.3(5) . . ?
C9 C4 C3 119.9(5) . . ?
C9 C4 C5 119.8(5) . . ?
C4 C5 B1 113.9(4) . . ?
C6 C5 C4 118.2(5) . . ?
C6 C5 B1 127.6(4) . . ?
C5 C6 H6 119.2 . . ?
C5 C6 C7 121.6(5) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 119.9(5) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.2(5) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 H9 119.8 . . ?
C8 C9 C4 120.3(5) . . ?
C8 C9 H9 119.8 . . ?
O1 B1 N1 109.2(4) . . ?
O1 B1 N2 111.0(4) . . ?
O1 B1 C5 113.8(4) . . ?
N2 B1 N1 98.0(4) . . ?
N2 B1 C5 107.4(4) . . ?
C5 B1 N1 116.3(4) . . ?

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 H1A O1 0.91 1.86 2.755(5) 166.6 3_554
N1 H1B O2 0.91 1.94 2.843(6) 170.9 1_545

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
N1 C1 C2 O2 168.9(5) . . . . ?
N1 C1 C2 N2 -9.3(6) . . . . ?
N2 N3 C3 C4 5.8(8) . . . . ?
N3 N2 C2 O2 -4.7(9) . . . . ?
N3 N2 C2 C1 173.3(4) . . . . ?
N3 N2 B1 O1 82.4(6) . . . . ?
N3 N2 B1 N1 -163.5(4) . . . . ?
N3 N2 B1 C5 -42.6(6) . . . . ?
N3 C3 C4 C5 -12.7(8) . . . . ?
N3 C3 C4 C9 164.9(6) . . . . ?
C1 N1 B1 O1 98.4(4) . . . . ?
C1 N1 B1 N2 -17.2(4) . . . . ?
C1 N1 B1 C5 -131.2(4) . . . . ?
C2 N2 N3 C3 -151.1(5) . . . . ?
C2 N2 B1 O1 -101.7(5) . . . . ?
C2 N2 B1 N1 12.5(5) . . . . ?
C2 N2 B1 C5 133.3(5) . . . . ?
C3 C4 C5 C6 176.3(5) . . . . ?
C3 C4 C5 B1 -9.2(7) . . . . ?
C3 C4 C9 C8 -176.9(5) . . . . ?
C4 C5 C6 C7 0.8(7) . . . . ?
C4 C5 B1 O1 -92.1(5) . . . . ?
C4 C5 B1 N1 139.7(4) . . . . ?
C4 C5 B1 N2 31.2(6) . . . . ?
C5 C4 C9 C8 0.8(8) . . . . ?
C5 C6 C7 C8 0.4(8) . . . . ?
C6 C5 B1 O1 81.8(6) . . . . ?
C6 C5 B1 N1 -46.4(7) . . . . ?
C6 C5 B1 N2 -154.9(5) . . . . ?
C6 C7 C8 C9 -1.1(8) . . . . ?
C7 C8 C9 C4 0.5(8) . . . . ?
C9 C4 C5 C6 -1.4(7) . . . . ?
C9 C4 C5 B1 173.1(4) . . . . ?
B1 N1 C1 C2 17.0(5) . . . . ?
B1 N2 N3 C3 24.7(7) . . . . ?
B1 N2 C2 O2 179.1(5) . . . . ?
B1 N2 C2 C1 -2.8(6) . . . . ?
B1 C5 C6 C7 -172.8(5) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id 1
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.1(7)
2 -0.1(7)

####################################################################### 
# 
# 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_jhbu1016b
_database_code_depnum_ccdc_archive 'CCDC 1518083'
_audit_update_record             
;
2016-11-20 deposited with the CCDC.
2017-08-08 downloaded from the CCDC.
;
_audit_creation_date             2016-10-10
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.10.04 svn.r3343 for OlexSys, GUI svn.r5250)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        'glyzide acetyl diazaborine'
_chemical_formula_moiety         'C10 H12 B N3 O2'
_chemical_formula_sum            'C10 H12 B N3 O2'
_chemical_formula_weight         217.04
_chemical_absolute_configuration unk
_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      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   8.5138(9)
_cell_length_b                   5.9254(6)
_cell_length_c                   10.2590(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.5113(11)
_cell_angle_gamma                90
_cell_volume                     498.69(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5325
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.04
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0539 before and 0.0494 after correction. The Ratio of minimum to maximum transmission is 0.9262. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       chunk
_exptl_crystal_F_000             228
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: water/dmso'
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8106
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.046
_diffrn_reflns_theta_min         2.483
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.989
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                1871
_reflns_number_total             1971
_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       'COSMO (BRUKER, V1.61, 2009)'
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 884 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1971
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0296
_refine_ls_restrained_S_all      1.033
_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)+(0.0355P)²+0.1140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0723
_refine_special_details          
'The structure was refined by Least Squares using version 2014/6 of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). All non-hydrogen atoms were refined anisotropically. Hydrogen atom positions were calculated geometrically and refined using the riding model.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 N3(H3A,H3B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C3(H3C,H3D,H3E)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_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 0.16015(19) 0.5393(3) 0.72095(16) 0.0184(4) Uani 1 1 d . . . . .
H1 H 0.1794 0.6772 0.7141 0.028 Uiso 1 1 calc GR . . A 1
O2 O -0.0391(2) -0.0898(3) 0.51655(18) 0.0253(4) Uani 1 1 d . . . . .
N1 N 0.1614(2) 0.1656(3) 0.6201(2) 0.0179(4) Uani 1 1 d . . . . .
N2 N 0.2535(2) 0.0126(3) 0.7133(2) 0.0196(4) Uani 1 1 d . . . . .
N3 N 0.0846(2) 0.4784(3) 0.4710(2) 0.0172(4) Uani 1 1 d . . . . .
H3A H 0.0345 0.6124 0.4763 0.021 Uiso 1 1 calc R . . . .
H3B H 0.1403 0.4905 0.4069 0.021 Uiso 1 1 calc R . . . .
C1 C 0.0262(3) 0.0979(4) 0.5294(3) 0.0193(5) Uani 1 1 d . . . . .
C2 C -0.0383(3) 0.2931(4) 0.4353(2) 0.0199(5) Uani 1 1 d . . . . .
H2A H -0.0538 0.2465 0.3400 0.024 Uiso 1 1 calc R . . . .
H2B H -0.1445 0.3445 0.4468 0.024 Uiso 1 1 calc R . . . .
C3 C 0.5064(3) -0.1012(4) 0.8584(3) 0.0250(6) Uani 1 1 d . . . . .
H3C H 0.5804 -0.1857 0.8179 0.038 Uiso 1 1 calc GR . . . .
H3D H 0.4331 -0.2064 0.8868 0.038 Uiso 1 1 calc GR . . . .
H3E H 0.5700 -0.0171 0.9372 0.038 Uiso 1 1 calc GR . . . .
C4 C 0.4082(3) 0.0605(4) 0.7564(2) 0.0192(5) Uani 1 1 d . . . . .
C5 C 0.4892(3) 0.2480(4) 0.7048(2) 0.0186(5) Uani 1 1 d . . . . .
C6 C 0.3975(3) 0.4207(4) 0.6261(2) 0.0173(5) Uani 1 1 d . . . . .
C7 C 0.4793(3) 0.5829(4) 0.5701(2) 0.0217(5) Uani 1 1 d . . . . .
H7 H 0.4185 0.6992 0.5153 0.026 Uiso 1 1 calc R . . . .
C8 C 0.6477(3) 0.5777(4) 0.5929(3) 0.0244(6) Uani 1 1 d . . . . .
H8 H 0.7011 0.6886 0.5533 0.029 Uiso 1 1 calc R . . . .
C9 C 0.7373(3) 0.4097(5) 0.6737(3) 0.0255(6) Uani 1 1 d . . . . .
H9 H 0.8526 0.4073 0.6907 0.031 Uiso 1 1 calc R . . . .
C10 C 0.6597(3) 0.2458(4) 0.7296(3) 0.0228(5) Uani 1 1 d . . . . .
H10 H 0.7219 0.1312 0.7849 0.027 Uiso 1 1 calc R . . . .
B1 B 0.2080(3) 0.4148(4) 0.6162(3) 0.0165(5) Uani 1 1 d . . . . .


_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 H1 0.8400 . ?
O1 B1 1.449(3) . ?
O2 C1 1.234(3) . ?
N1 N2 1.397(3) . ?
N1 C1 1.333(3) . ?
N1 B1 1.532(3) . ?
N2 C4 1.303(3) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 C2 1.493(3) . ?
N3 B1 1.621(3) . ?
C1 C2 1.512(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3C 0.9800 . ?
C3 H3D 0.9800 . ?
C3 H3E 0.9800 . ?
C3 C4 1.498(3) . ?
C4 C5 1.478(3) . ?
C5 C6 1.404(3) . ?
C5 C10 1.405(3) . ?
C6 C7 1.397(3) . ?
C6 B1 1.590(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.386(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(4) . ?
C10 H10 0.9500 . ?

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 O1 H1 109.5 . . ?
N2 N1 B1 122.78(18) . . ?
C1 N1 N2 120.28(19) . . ?
C1 N1 B1 116.94(19) . . ?
C4 N2 N1 115.0(2) . . ?
H3A N3 H3B 108.6 . . ?
C2 N3 H3A 110.3 . . ?
C2 N3 H3B 110.3 . . ?
C2 N3 B1 107.08(17) . . ?
B1 N3 H3A 110.3 . . ?
B1 N3 H3B 110.3 . . ?
O2 C1 N1 128.7(2) . . ?
O2 C1 C2 123.0(2) . . ?
N1 C1 C2 108.28(19) . . ?
N3 C2 C1 107.14(18) . . ?
N3 C2 H2A 110.3 . . ?
N3 C2 H2B 110.3 . . ?
C1 C2 H2A 110.3 . . ?
C1 C2 H2B 110.3 . . ?
H2A C2 H2B 108.5 . . ?
H3C C3 H3D 109.5 . . ?
H3C C3 H3E 109.5 . . ?
H3D C3 H3E 109.5 . . ?
C4 C3 H3C 109.5 . . ?
C4 C3 H3D 109.5 . . ?
C4 C3 H3E 109.5 . . ?
N2 C4 C3 115.0(2) . . ?
N2 C4 C5 124.6(2) . . ?
C5 C4 C3 120.2(2) . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 C10 120.0(2) . . ?
C10 C5 C4 119.1(2) . . ?
C5 C6 B1 114.8(2) . . ?
C7 C6 C5 118.5(2) . . ?
C7 C6 B1 126.7(2) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.4(2) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.6(2) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 H9 119.8 . . ?
C5 C10 H10 119.9 . . ?
C9 C10 C5 120.2(2) . . ?
C9 C10 H10 119.9 . . ?
O1 B1 N1 110.19(19) . . ?
O1 B1 N3 108.7(2) . . ?
O1 B1 C6 115.1(2) . . ?
N1 B1 N3 98.00(17) . . ?
N1 B1 C6 106.6(2) . . ?
C6 B1 N3 116.81(19) . . ?

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
N3 H3A O2 0.91 1.95 2.853(3) 169.4 1_565
N3 H3B O1 0.91 1.97 2.808(2) 152.8 2_564

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
O2 C1 C2 N3 -172.2(2) . . . . ?
N1 N2 C4 C3 178.9(2) . . . . ?
N1 N2 C4 C5 -5.5(3) . . . . ?
N1 C1 C2 N3 6.1(3) . . . . ?
N2 N1 C1 O2 3.1(4) . . . . ?
N2 N1 C1 C2 -175.0(2) . . . . ?
N2 N1 B1 O1 -79.3(3) . . . . ?
N2 N1 B1 N3 167.3(2) . . . . ?
N2 N1 B1 C6 46.2(3) . . . . ?
N2 C4 C5 C6 14.7(4) . . . . ?
N2 C4 C5 C10 -162.1(2) . . . . ?
C1 N1 N2 C4 152.5(2) . . . . ?
C1 N1 B1 O1 100.5(2) . . . . ?
C1 N1 B1 N3 -12.9(2) . . . . ?
C1 N1 B1 C6 -134.1(2) . . . . ?
C2 N3 B1 O1 -99.2(2) . . . . ?
C2 N3 B1 N1 15.4(2) . . . . ?
C2 N3 B1 C6 128.6(2) . . . . ?
C3 C4 C5 C6 -169.9(2) . . . . ?
C3 C4 C5 C10 13.3(3) . . . . ?
C4 C5 C6 C7 -174.5(2) . . . . ?
C4 C5 C6 B1 8.2(3) . . . . ?
C4 C5 C10 C9 175.0(2) . . . . ?
C5 C6 C7 C8 -1.1(3) . . . . ?
C5 C6 B1 O1 89.3(2) . . . . ?
C5 C6 B1 N1 -33.1(3) . . . . ?
C5 C6 B1 N3 -141.4(2) . . . . ?
C6 C5 C10 C9 -1.8(3) . . . . ?
C6 C7 C8 C9 -0.6(4) . . . . ?
C7 C6 B1 O1 -87.8(3) . . . . ?
C7 C6 B1 N1 149.8(2) . . . . ?
C7 C6 B1 N3 41.5(3) . . . . ?
C7 C8 C9 C10 1.1(4) . . . . ?
C8 C9 C10 C5 0.1(4) . . . . ?
C10 C5 C6 C7 2.2(3) . . . . ?
C10 C5 C6 B1 -175.1(2) . . . . ?
B1 N1 N2 C4 -27.7(3) . . . . ?
B1 N1 C1 O2 -176.7(2) . . . . ?
B1 N1 C1 C2 5.2(3) . . . . ?
B1 N3 C2 C1 -13.9(2) . . . . ?
B1 C6 C7 C8 175.9(2) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id 2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_jhbu1016a
_database_code_depnum_ccdc_archive 'CCDC 1518085'
_audit_update_record             
;
2016-11-20 deposited with the CCDC.
2017-08-08 downloaded from the CCDC.
;
_audit_creation_date             2016-10-07
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.10.04 svn.r3343 for OlexSys, GUI svn.r5250)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        'propazide diazaborine'
_chemical_formula_moiety         'C20 H20 B2 N4 O3'
_chemical_formula_sum            'C20 H20 B2 N4 O3'
_chemical_formula_weight         386.02
_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 0.0181 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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.67160(10)
_cell_length_b                   11.08430(10)
_cell_length_c                   12.4325(2)
_cell_angle_alpha                103.9410(10)
_cell_angle_beta                 97.63
_cell_angle_gamma                109.88
_cell_volume                     937.84(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9887
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.23
_cell_measurement_theta_min      4.46
_shelx_estimated_absorpt_T_max   0.824
_shelx_estimated_absorpt_T_min   0.728
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0443 before and 0.0326 after correction. The Ratio of minimum to maximum transmission is 0.9137. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.455
_exptl_crystal_size_mid          0.355
_exptl_crystal_size_min          0.27
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11521
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.227
_diffrn_reflns_theta_min         4.457
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3387
_reflns_number_total             3527
_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       'COSMO (BRUKER, V1.61, 2009)'
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0443(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3527
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0547P)²+0.3553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1028
_refine_special_details          
'The structure was refined by Least Squares using version 2014/6 of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). All non-hydrogen atoms were refined anisotropically. Hydrogen atom positions were calculated geometrically and refined using the riding model.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_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 0.28722(11) 0.68366(8) 0.74559(7) 0.0192(2) Uani 1 1 d . . . . .
O2 O 0.49087(12) 0.55576(8) 0.73174(7) 0.0219(2) Uani 1 1 d . . . . .
O3 O 0.47095(11) 0.79434(8) 0.62503(7) 0.0204(2) Uani 1 1 d . . . . .
N1 N 0.63780(13) 0.78194(10) 0.80369(8) 0.0195(2) Uani 1 1 d . . . . .
N2 N 0.80681(14) 0.88921(10) 0.87077(9) 0.0241(2) Uani 1 1 d . . . . .
N3 N 0.30950(14) 0.56826(10) 0.55706(8) 0.0195(2) Uani 1 1 d . . . . .
N4 N 0.23789(15) 0.45725(11) 0.45841(9) 0.0255(2) Uani 1 1 d . . . . .
C1 C 0.45536(17) 0.94056(12) 0.81444(10) 0.0204(3) Uani 1 1 d . . . . .
C2 C 0.29815(18) 0.97656(13) 0.80186(11) 0.0257(3) Uani 1 1 d . . . . .
H2 H 0.1806 0.9126 0.7523 0.031 Uiso 1 1 calc R . . . .
C3 C 0.3097(2) 1.10368(14) 0.86021(12) 0.0296(3) Uani 1 1 d . . . . .
H3 H 0.2014 1.1265 0.8490 0.036 Uiso 1 1 calc R . . . .
C4 C 0.4791(2) 1.19772(13) 0.93504(12) 0.0288(3) Uani 1 1 d . . . . .
H4 H 0.4868 1.2846 0.9752 0.035 Uiso 1 1 calc R . . . .
C5 C 0.63623(19) 1.16419(13) 0.95080(11) 0.0262(3) Uani 1 1 d . . . . .
H5 H 0.7516 1.2275 1.0030 0.031 Uiso 1 1 calc R . . . .
C6 C 0.62544(17) 1.03723(12) 0.89008(10) 0.0212(3) Uani 1 1 d . . . . .
C7 C 0.79253(17) 1.00319(12) 0.90774(11) 0.0243(3) Uani 1 1 d . . . . .
H7 H 0.9069 1.0756 0.9530 0.029 Uiso 1 1 calc R . . . .
C8 C 0.64054(17) 0.66105(12) 0.78904(10) 0.0209(3) Uani 1 1 d . . . . .
C9 C 0.80993(19) 0.63419(13) 0.83506(12) 0.0302(3) Uani 1 1 d . . . . .
H9A H 0.8501 0.5870 0.7708 0.036 Uiso 1 1 calc R . . . .
H9B H 0.9172 0.7210 0.8768 0.036 Uiso 1 1 calc R . . . .
C10 C 0.7661(3) 0.5502(3) 0.91354(19) 0.0754(8) Uani 1 1 d . . . . .
H10A H 0.6524 0.4679 0.8748 0.113 Uiso 1 1 calc GR . . . .
H10B H 0.7428 0.6016 0.9822 0.113 Uiso 1 1 calc GR . . . .
H10C H 0.8745 0.5261 0.9350 0.113 Uiso 1 1 calc GR . . . .
C11 C 0.13949(16) 0.42213(12) 0.67405(10) 0.0214(3) Uani 1 1 d . . . . .
C12 C 0.07828(18) 0.39377(13) 0.76905(11) 0.0259(3) Uani 1 1 d . . . . .
H12 H 0.1203 0.4636 0.8397 0.031 Uiso 1 1 calc R . . . .
C13 C -0.04338(19) 0.26480(14) 0.76208(12) 0.0305(3) Uani 1 1 d . . . . .
H13 H -0.0835 0.2475 0.8278 0.037 Uiso 1 1 calc R . . . .
C14 C -0.10656(19) 0.16117(13) 0.65970(13) 0.0305(3) Uani 1 1 d . . . . .
H14 H -0.1878 0.0728 0.6556 0.037 Uiso 1 1 calc R . . . .
C15 C -0.05057(18) 0.18724(13) 0.56383(12) 0.0287(3) Uani 1 1 d . . . . .
H15 H -0.0949 0.1171 0.4932 0.034 Uiso 1 1 calc R . . . .
C16 C 0.07213(17) 0.31762(12) 0.57087(11) 0.0235(3) Uani 1 1 d . . . . .
C17 C 0.13153(18) 0.34488(13) 0.46944(11) 0.0275(3) Uani 1 1 d . . . . .
H17 H 0.0854 0.2694 0.4025 0.033 Uiso 1 1 calc R . . . .
C18 C 0.39936(16) 0.68529(12) 0.54053(10) 0.0187(3) Uani 1 1 d . . . . .
C19 C 0.42319(17) 0.69483(12) 0.42487(10) 0.0222(3) Uani 1 1 d . . . . .
H19A H 0.2965 0.6727 0.3763 0.027 Uiso 1 1 calc R . . . .
H19B H 0.4719 0.6264 0.3900 0.027 Uiso 1 1 calc R . . . .
C20 C 0.5574(2) 0.83236(14) 0.42526(12) 0.0303(3) Uani 1 1 d . . . . .
H20A H 0.5669 0.8304 0.3471 0.045 Uiso 1 1 calc GR . . . .
H20B H 0.6840 0.8548 0.4722 0.045 Uiso 1 1 calc GR . . . .
H20C H 0.5080 0.9005 0.4568 0.045 Uiso 1 1 calc GR . . . .
B1 B 0.44867(18) 0.79693(14) 0.75017(11) 0.0195(3) Uani 1 1 d . . . . .
B2 B 0.29608(18) 0.56350(14) 0.68165(11) 0.0198(3) Uani 1 1 d . . . . .


_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 B1 1.4153(15) . ?
O1 B2 1.4058(16) . ?
O2 C8 1.2880(15) . ?
O2 B2 1.5793(15) . ?
O3 C18 1.2844(15) . ?
O3 B1 1.5820(14) . ?
N1 N2 1.4061(14) . ?
N1 C8 1.3159(16) . ?
N1 B1 1.5926(15) . ?
N2 C7 1.2834(17) . ?
N3 N4 1.3980(14) . ?
N3 C18 1.3260(16) . ?
N3 B2 1.5781(16) . ?
N4 C17 1.2872(17) . ?
C1 C2 1.3948(17) . ?
C1 C6 1.4046(17) . ?
C1 B1 1.5800(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.3876(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3808(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.3962(18) . ?
C6 C7 1.4586(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.5008(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.498(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.3928(17) . ?
C11 C16 1.3983(18) . ?
C11 B2 1.5893(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.3906(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.4051(17) . ?
C16 C17 1.4601(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.4974(16) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.5206(17) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
B2 O1 B1 110.98(9) . . ?
C8 O2 B2 122.84(9) . . ?
C18 O3 B1 122.45(9) . . ?
N2 N1 B1 125.26(10) . . ?
C8 N1 N2 115.11(10) . . ?
C8 N1 B1 119.59(10) . . ?
C7 N2 N1 115.55(10) . . ?
N4 N3 B2 125.83(10) . . ?
C18 N3 N4 114.63(10) . . ?
C18 N3 B2 119.53(10) . . ?
C17 N4 N3 115.98(10) . . ?
C2 C1 C6 117.46(12) . . ?
C2 C1 B1 123.19(11) . . ?
C6 C1 B1 119.34(11) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.44(12) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.21(12) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.67(12) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 119.99(12) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C7 119.40(11) . . ?
C5 C6 C1 121.22(12) . . ?
C5 C6 C7 119.36(11) . . ?
N2 C7 C6 129.11(11) . . ?
N2 C7 H7 115.4 . . ?
C6 C7 H7 115.4 . . ?
O2 C8 N1 120.01(10) . . ?
O2 C8 C9 115.52(11) . . ?
N1 C8 C9 124.47(11) . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 C8 111.71(12) . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 118.02(11) . . ?
C12 C11 B2 122.45(11) . . ?
C16 C11 B2 119.28(11) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.03(12) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.47(12) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.60(12) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.90(13) . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C15 120.96(12) . . ?
C11 C16 C17 119.24(11) . . ?
C15 C16 C17 119.80(12) . . ?
N4 C17 C16 128.80(12) . . ?
N4 C17 H17 115.6 . . ?
C16 C17 H17 115.6 . . ?
O3 C18 N3 120.15(11) . . ?
O3 C18 C19 118.11(10) . . ?
N3 C18 C19 121.74(11) . . ?
C18 C19 H19A 108.7 . . ?
C18 C19 H19B 108.7 . . ?
C18 C19 C20 114.25(10) . . ?
H19A C19 H19B 107.6 . . ?
C20 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 B1 O3 109.62(9) . . ?
O1 B1 N1 109.64(10) . . ?
O1 B1 C1 117.14(10) . . ?
O3 B1 N1 102.18(9) . . ?
C1 B1 O3 108.12(9) . . ?
C1 B1 N1 109.08(10) . . ?
O1 B2 O2 109.33(9) . . ?
O1 B2 N3 109.80(10) . . ?
O1 B2 C11 119.97(10) . . ?
O2 B2 C11 104.00(9) . . ?
N3 B2 O2 103.46(9) . . ?
N3 B2 C11 108.91(10) . . ?

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
O2 C8 C9 C10 -59.55(18) . . . . ?
O3 C18 C19 C20 8.87(15) . . . . ?
N1 N2 C7 C6 0.07(19) . . . . ?
N1 C8 C9 C10 120.53(17) . . . . ?
N2 N1 C8 O2 177.96(10) . . . . ?
N2 N1 C8 C9 -2.12(17) . . . . ?
N2 N1 B1 O1 -147.48(10) . . . . ?
N2 N1 B1 O3 96.30(12) . . . . ?
N2 N1 B1 C1 -17.99(14) . . . . ?
N3 N4 C17 C16 1.2(2) . . . . ?
N3 C18 C19 C20 -170.28(11) . . . . ?
N4 N3 C18 O3 179.91(9) . . . . ?
N4 N3 C18 C19 -0.96(16) . . . . ?
N4 N3 B2 O1 -149.40(10) . . . . ?
N4 N3 B2 O2 93.98(12) . . . . ?
N4 N3 B2 C11 -16.19(15) . . . . ?
C1 C2 C3 C4 -1.4(2) . . . . ?
C1 C6 C7 N2 -6.8(2) . . . . ?
C2 C1 C6 C5 0.36(17) . . . . ?
C2 C1 C6 C7 178.78(11) . . . . ?
C2 C1 B1 O1 -43.22(16) . . . . ?
C2 C1 B1 O3 81.17(13) . . . . ?
C2 C1 B1 N1 -168.45(10) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C3 C4 C5 C6 1.21(19) . . . . ?
C4 C5 C6 C1 -1.51(18) . . . . ?
C4 C5 C6 C7 -179.92(11) . . . . ?
C5 C6 C7 N2 171.60(12) . . . . ?
C6 C1 C2 C3 1.07(18) . . . . ?
C6 C1 B1 O1 135.43(11) . . . . ?
C6 C1 B1 O3 -100.18(11) . . . . ?
C6 C1 B1 N1 10.19(14) . . . . ?
C8 O2 B2 O1 -24.34(14) . . . . ?
C8 O2 B2 N3 92.61(12) . . . . ?
C8 O2 B2 C11 -153.62(10) . . . . ?
C8 N1 N2 C7 -164.40(11) . . . . ?
C8 N1 B1 O1 30.28(14) . . . . ?
C8 N1 B1 O3 -85.93(12) . . . . ?
C8 N1 B1 C1 159.78(10) . . . . ?
C11 C12 C13 C14 0.0(2) . . . . ?
C11 C16 C17 N4 -2.3(2) . . . . ?
C12 C11 C16 C15 -1.27(18) . . . . ?
C12 C11 C16 C17 179.07(11) . . . . ?
C12 C11 B2 O1 -44.33(17) . . . . ?
C12 C11 B2 O2 78.20(13) . . . . ?
C12 C11 B2 N3 -171.98(10) . . . . ?
C12 C13 C14 C15 -1.1(2) . . . . ?
C13 C14 C15 C16 1.0(2) . . . . ?
C14 C15 C16 C11 0.18(19) . . . . ?
C14 C15 C16 C17 179.85(12) . . . . ?
C15 C16 C17 N4 177.98(13) . . . . ?
C16 C11 C12 C13 1.17(18) . . . . ?
C16 C11 B2 O1 141.57(12) . . . . ?
C16 C11 B2 O2 -95.91(12) . . . . ?
C16 C11 B2 N3 13.91(15) . . . . ?
C18 O3 B1 O1 -22.99(14) . . . . ?
C18 O3 B1 N1 93.24(11) . . . . ?
C18 O3 B1 C1 -151.76(10) . . . . ?
C18 N3 N4 C17 -172.36(11) . . . . ?
C18 N3 B2 O1 32.35(14) . . . . ?
C18 N3 B2 O2 -84.27(12) . . . . ?
C18 N3 B2 C11 165.56(10) . . . . ?
B1 O1 B2 O2 54.60(12) . . . . ?
B1 O1 B2 N3 -58.26(12) . . . . ?
B1 O1 B2 C11 174.48(10) . . . . ?
B1 O3 C18 N3 -2.88(16) . . . . ?
B1 O3 C18 C19 177.96(10) . . . . ?
B1 N1 N2 C7 13.45(16) . . . . ?
B1 N1 C8 O2 -0.02(16) . . . . ?
B1 N1 C8 C9 179.89(11) . . . . ?
B1 C1 C2 C3 179.75(11) . . . . ?
B1 C1 C6 C5 -178.36(11) . . . . ?
B1 C1 C6 C7 0.05(16) . . . . ?
B2 O1 B1 O3 53.64(12) . . . . ?
B2 O1 B1 N1 -57.77(12) . . . . ?
B2 O1 B1 C1 177.27(10) . . . . ?
B2 O2 C8 N1 -3.03(17) . . . . ?
B2 O2 C8 C9 177.05(10) . . . . ?
B2 N3 N4 C17 9.31(17) . . . . ?
B2 N3 C18 O3 -1.65(16) . . . . ?
B2 N3 C18 C19 177.48(10) . . . . ?
B2 C11 C12 C13 -173.00(11) . . . . ?
B2 C11 C16 C15 173.10(11) . . . . ?
B2 C11 C16 C17 -6.57(17) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id 3
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sbbu915a
_database_code_depnum_ccdc_archive 'CCDC 1518086'
_audit_update_record             
;
2016-11-20 deposited with the CCDC.
2017-08-08 downloaded from the CCDC.
;
_audit_creation_date             2015-09-22
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2015.09.21 svn.r3230 for OlexSys, GUI svn.r5097)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        'acetyl diazaborine'
_chemical_formula_moiety         'C18 H16 B2 N4 O3'
_chemical_formula_sum            'C18 H16 B2 N4 O3'
_chemical_formula_weight         357.97
_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 0.0181 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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.35750(10)
_cell_length_b                   8.05570(10)
_cell_length_c                   15.1438(2)
_cell_angle_alpha                95.9130(10)
_cell_angle_beta                 94.5590(10)
_cell_angle_gamma                110.0140(10)
_cell_volume                     832.53(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.27
_cell_measurement_theta_min      5.90
_shelx_estimated_absorpt_T_max   0.833
_shelx_estimated_absorpt_T_min   0.746
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0450 before and 0.0368 after correction. The Ratio of minimum to maximum transmission is 0.9213. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       chunk
_exptl_crystal_F_000             372
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.249
_exptl_crystal_size_min          0.238
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a nylon loop using 
Paratone oil.  Data  were measured using omega and phi scans of 1.0° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structures are solved 
by the direct method using the SHELXS-97 program and refined by least squares 
method on F2, SHELXL-97, incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12241
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.259
_diffrn_reflns_theta_min         5.903
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2997
_reflns_number_total             3123
_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       'COSMO (BRUKER, V1.61, 2009)'
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0113(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3123
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.030
_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)+(0.0469P)²+0.3059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0933
_refine_special_details          
;
Structure refined by least squares method on F2, SHELXL-97, 
incorporated in Olex2 (Dolomanov et al., 2009). 
All H atoms were placed in calculated positions and refined using a riding 
model.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.80104(11) 0.02779(10) 0.69377(5) 0.01891(19) Uani 1 1 d . . . . .
O2 O 1.06527(11) 0.00009(11) 0.79238(6) 0.0233(2) Uani 1 1 d . . . . .
O3 O 0.95063(11) 0.35180(10) 0.72365(5) 0.0216(2) Uani 1 1 d . . . . .
N1 N 0.89801(13) 0.20355(13) 0.84328(6) 0.0204(2) Uani 1 1 d . . . . .
N2 N 0.89903(16) 0.22284(14) 0.93673(7) 0.0270(2) Uani 1 1 d . . . . .
N3 N 1.14780(14) 0.16607(13) 0.67965(7) 0.0220(2) Uani 1 1 d . . . . .
N4 N 1.30211(14) 0.24808(15) 0.63064(8) 0.0300(3) Uani 1 1 d . . . . .
C1 C 1.19310(16) 0.07991(15) 0.74214(8) 0.0224(3) Uani 1 1 d . . . . .
C2 C 1.39205(18) 0.07361(18) 0.76201(9) 0.0309(3) Uani 1 1 d . . . . .
H2A H 1.3870 -0.0179 0.8006 0.046 Uiso 1 1 calc GR . . . .
H2B H 1.4803 0.1900 0.7925 0.046 Uiso 1 1 calc GR . . . .
H2C H 1.4397 0.0445 0.7060 0.046 Uiso 1 1 calc GR . . . .
C3 C 0.71411(16) -0.13302(15) 0.82919(8) 0.0208(2) Uani 1 1 d . . . . .
C4 C 0.58888(17) -0.29565(16) 0.78224(8) 0.0249(3) Uani 1 1 d . . . . .
H4 H 0.5941 -0.3223 0.7201 0.030 Uiso 1 1 calc R . . . .
C5 C 0.45673(18) -0.41905(17) 0.82526(9) 0.0311(3) Uani 1 1 d . . . . .
H5 H 0.3706 -0.5279 0.7920 0.037 Uiso 1 1 calc R . . . .
C6 C 0.44943(19) -0.38486(18) 0.91621(10) 0.0339(3) Uani 1 1 d . . . . .
H6 H 0.3602 -0.4707 0.9454 0.041 Uiso 1 1 calc R . . . .
C7 C 0.57283(19) -0.22505(18) 0.96422(9) 0.0315(3) Uani 1 1 d . . . . .
H7 H 0.5699 -0.2014 1.0268 0.038 Uiso 1 1 calc R . . . .
C8 C 0.70187(17) -0.09837(16) 0.92055(8) 0.0242(3) Uani 1 1 d . . . . .
C9 C 0.81432(19) 0.07866(17) 0.96930(8) 0.0282(3) Uani 1 1 d . . . . .
H9 H 0.8261 0.0882 1.0327 0.034 Uiso 1 1 calc R . . . .
C10 C 0.93027(15) 0.35174(15) 0.80717(8) 0.0201(2) Uani 1 1 d . . . . .
C11 C 0.94032(18) 0.52320(16) 0.85888(8) 0.0271(3) Uani 1 1 d . . . . .
H11A H 0.8088 0.5168 0.8700 0.041 Uiso 1 1 calc GR . . . .
H11B H 0.9964 0.6213 0.8246 0.041 Uiso 1 1 calc GR . . . .
H11C H 1.0223 0.5441 0.9161 0.041 Uiso 1 1 calc GR . . . .
C12 C 0.89724(17) 0.20823(14) 0.56307(8) 0.0212(2) Uani 1 1 d . . . . .
C13 C 0.71288(17) 0.18841(16) 0.52223(8) 0.0247(3) Uani 1 1 d . . . . .
H13 H 0.6028 0.1456 0.5535 0.030 Uiso 1 1 calc R . . . .
C14 C 0.68784(19) 0.23038(17) 0.43655(9) 0.0293(3) Uani 1 1 d . . . . .
H14 H 0.5610 0.2144 0.4094 0.035 Uiso 1 1 calc R . . . .
C15 C 0.8479(2) 0.29583(17) 0.39024(9) 0.0313(3) Uani 1 1 d . . . . .
H15 H 0.8305 0.3264 0.3320 0.038 Uiso 1 1 calc R . . . .
C16 C 1.0320(2) 0.31618(17) 0.42913(9) 0.0308(3) Uani 1 1 d . . . . .
H16 H 1.1415 0.3605 0.3977 0.037 Uiso 1 1 calc R . . . .
C17 C 1.05650(18) 0.27122(15) 0.51504(8) 0.0249(3) Uani 1 1 d . . . . .
C18 C 1.25074(18) 0.29367(18) 0.55645(9) 0.0305(3) Uani 1 1 d . . . . .
H18 H 1.3545 0.3503 0.5238 0.037 Uiso 1 1 calc R . . . .
B1 B 0.86006(18) 0.01771(17) 0.78322(9) 0.0199(3) Uani 1 1 d . . . . .
B2 B 0.93524(18) 0.17441(17) 0.66258(9) 0.0202(3) Uani 1 1 d . . . . .


_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 B1 1.4083(15) . ?
O1 B2 1.4085(15) . ?
O2 C1 1.2952(15) . ?
O2 B1 1.5609(14) . ?
O3 C10 1.2855(14) . ?
O3 B2 1.5844(15) . ?
N1 N2 1.4068(14) . ?
N1 C10 1.3197(15) . ?
N1 B1 1.5936(15) . ?
N2 C9 1.2853(17) . ?
N3 N4 1.4134(14) . ?
N3 C1 1.3161(16) . ?
N3 B2 1.5901(15) . ?
N4 C18 1.2855(18) . ?
C1 C2 1.4899(16) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.3959(17) . ?
C3 C8 1.3992(17) . ?
C3 B1 1.5852(17) . ?
C4 H4 0.9500 . ?
C4 C5 1.3894(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.383(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.3984(17) . ?
C8 C9 1.4634(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.4915(16) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.3950(17) . ?
C12 C17 1.4014(16) . ?
C12 B2 1.5789(17) . ?
C13 H13 0.9500 . ?
C13 C14 1.3881(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.3924(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.4004(18) . ?
C17 C18 1.4580(18) . ?
C18 H18 0.9500 . ?

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 O1 B2 111.09(9) . . ?
C1 O2 B1 119.55(9) . . ?
C10 O3 B2 120.67(9) . . ?
N2 N1 B1 123.53(9) . . ?
C10 N1 N2 115.32(10) . . ?
C10 N1 B1 121.15(10) . . ?
C9 N2 N1 115.56(10) . . ?
N4 N3 B2 124.04(9) . . ?
C1 N3 N4 114.50(10) . . ?
C1 N3 B2 121.46(10) . . ?
C18 N4 N3 115.20(10) . . ?
O2 C1 N3 120.71(10) . . ?
O2 C1 C2 116.18(11) . . ?
N3 C1 C2 123.06(11) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 C8 117.95(11) . . ?
C4 C3 B1 123.34(11) . . ?
C8 C3 B1 118.62(10) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.82(12) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.63(12) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.58(12) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.89(12) . . ?
C8 C7 H7 120.1 . . ?
C3 C8 C9 119.22(11) . . ?
C7 C8 C3 121.09(12) . . ?
C7 C8 C9 119.50(12) . . ?
N2 C9 C8 127.88(11) . . ?
N2 C9 H9 116.1 . . ?
C8 C9 H9 116.1 . . ?
O3 C10 N1 120.17(10) . . ?
O3 C10 C11 117.04(10) . . ?
N1 C10 C11 122.78(11) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 118.12(11) . . ?
C13 C12 B2 122.86(10) . . ?
C17 C12 B2 118.90(10) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 120.97(11) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.28(12) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.86(12) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.76(12) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 C18 119.12(11) . . ?
C16 C17 C12 121.00(12) . . ?
C16 C17 C18 119.87(11) . . ?
N4 C18 C17 129.45(11) . . ?
N4 C18 H18 115.3 . . ?
C17 C18 H18 115.3 . . ?
O1 B1 O2 110.56(9) . . ?
O1 B1 N1 109.64(9) . . ?
O1 B1 C3 116.41(10) . . ?
O2 B1 N1 102.66(8) . . ?
O2 B1 C3 109.38(9) . . ?
C3 B1 N1 107.26(9) . . ?
O1 B2 O3 108.90(9) . . ?
O1 B2 N3 109.21(9) . . ?
O1 B2 C12 119.14(10) . . ?
O3 B2 N3 103.57(8) . . ?
C12 B2 O3 105.77(9) . . ?
C12 B2 N3 109.11(9) . . ?

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
N1 N2 C9 C8 -6.36(19) . . . . ?
N2 N1 C10 O3 173.42(9) . . . . ?
N2 N1 C10 C11 -8.02(15) . . . . ?
N2 N1 B1 O1 159.55(9) . . . . ?
N2 N1 B1 O2 -82.92(12) . . . . ?
N2 N1 B1 C3 32.29(13) . . . . ?
N3 N4 C18 C17 -0.8(2) . . . . ?
N4 N3 C1 O2 179.42(10) . . . . ?
N4 N3 C1 C2 1.88(16) . . . . ?
N4 N3 B2 O1 156.28(10) . . . . ?
N4 N3 B2 O3 -87.80(12) . . . . ?
N4 N3 B2 C12 24.49(14) . . . . ?
C1 O2 B1 O1 34.06(13) . . . . ?
C1 O2 B1 N1 -82.82(11) . . . . ?
C1 O2 B1 C3 163.52(10) . . . . ?
C1 N3 N4 C18 163.42(11) . . . . ?
C1 N3 B2 O1 -23.73(14) . . . . ?
C1 N3 B2 O3 92.18(12) . . . . ?
C1 N3 B2 C12 -155.52(10) . . . . ?
C3 C4 C5 C6 -1.43(19) . . . . ?
C3 C8 C9 N2 14.3(2) . . . . ?
C4 C3 C8 C7 2.11(17) . . . . ?
C4 C3 C8 C9 -172.82(10) . . . . ?
C4 C3 B1 O1 30.48(16) . . . . ?
C4 C3 B1 O2 -95.70(12) . . . . ?
C4 C3 B1 N1 153.66(10) . . . . ?
C4 C5 C6 C7 1.1(2) . . . . ?
C5 C6 C7 C8 0.9(2) . . . . ?
C6 C7 C8 C3 -2.50(19) . . . . ?
C6 C7 C8 C9 172.41(12) . . . . ?
C7 C8 C9 N2 -160.71(13) . . . . ?
C8 C3 C4 C5 -0.15(17) . . . . ?
C8 C3 B1 O1 -145.92(10) . . . . ?
C8 C3 B1 O2 87.90(12) . . . . ?
C8 C3 B1 N1 -22.74(13) . . . . ?
C10 O3 B2 O1 32.47(13) . . . . ?
C10 O3 B2 N3 -83.66(11) . . . . ?
C10 O3 B2 C12 161.63(9) . . . . ?
C10 N1 N2 C9 160.59(11) . . . . ?
C10 N1 B1 O1 -20.15(14) . . . . ?
C10 N1 B1 O2 97.38(11) . . . . ?
C10 N1 B1 C3 -147.41(10) . . . . ?
C12 C13 C14 C15 -0.94(19) . . . . ?
C12 C17 C18 N4 7.4(2) . . . . ?
C13 C12 C17 C16 1.17(17) . . . . ?
C13 C12 C17 C18 179.77(11) . . . . ?
C13 C12 B2 O1 41.02(16) . . . . ?
C13 C12 B2 O3 -81.85(12) . . . . ?
C13 C12 B2 N3 167.31(10) . . . . ?
C13 C14 C15 C16 1.12(19) . . . . ?
C14 C15 C16 C17 -0.16(19) . . . . ?
C15 C16 C17 C12 -1.00(18) . . . . ?
C15 C16 C17 C18 -179.60(12) . . . . ?
C16 C17 C18 N4 -174.01(13) . . . . ?
C17 C12 C13 C14 -0.20(18) . . . . ?
C17 C12 B2 O1 -142.93(11) . . . . ?
C17 C12 B2 O3 94.20(12) . . . . ?
C17 C12 B2 N3 -16.65(14) . . . . ?
B1 O1 B2 O3 -59.46(11) . . . . ?
B1 O1 B2 N3 53.00(12) . . . . ?
B1 O1 B2 C12 179.23(10) . . . . ?
B1 O2 C1 N3 -4.37(16) . . . . ?
B1 O2 C1 C2 173.32(10) . . . . ?
B1 N1 N2 C9 -19.13(16) . . . . ?
B1 N1 C10 O3 -6.85(15) . . . . ?
B1 N1 C10 C11 171.70(10) . . . . ?
B1 C3 C4 C5 -176.58(11) . . . . ?
B1 C3 C8 C7 178.70(11) . . . . ?
B1 C3 C8 C9 3.78(16) . . . . ?
B2 O1 B1 O2 -58.80(11) . . . . ?
B2 O1 B1 N1 53.68(12) . . . . ?
B2 O1 B1 C3 175.61(9) . . . . ?
B2 O3 C10 N1 0.65(15) . . . . ?
B2 O3 C10 C11 -177.99(9) . . . . ?
B2 N3 N4 C18 -16.59(16) . . . . ?
B2 N3 C1 O2 -0.57(17) . . . . ?
B2 N3 C1 C2 -178.10(10) . . . . ?
B2 C12 C13 C14 175.88(11) . . . . ?
B2 C12 C17 C16 -175.07(11) . . . . ?
B2 C12 C17 C18 3.54(16) . . . . ?

_contact_Crystallographer_email  staples@chemistry.msu.com
_contact_Crystallographer_name   'Richard Staples'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id Sample
_olex2_submission_special_instructions 'No special instructions were received'
