# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1110th19
_database_code_depnum_ccdc_archive 'CCDC 1848682'
_audit_update_record             
;
2018-06-11 deposited with the CCDC.
2019-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014


_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 B N2 O3'
_chemical_formula_sum            'C15 H13 B N2 O3'
_chemical_formula_weight         280.08
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.2723(8)
_cell_length_b                   11.6971(6)
_cell_length_c                   10.6896(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.099(6)
_cell_angle_gamma                90
_cell_volume                     1383.10(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(1)
_cell_measurement_reflns_used    1486
_cell_measurement_theta_min      3.9770
_cell_measurement_theta_max      28.9570

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.986

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent (2013)
;

_exptl_absorpt_correction_T_min  0.99066
_exptl_absorpt_correction_T_max  1.00000

_diffrn_ambient_temperature      223(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_detector_area_resol_mean 16.0774
_diffrn_measurement_method       'ω scans'

_diffrn_reflns_number            6482
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.402
_diffrn_reflns_theta_max         30.476
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3718
_reflns_number_gt                2422
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_cell_refinement       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0883P)²+0.2766P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3718
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1738
_refine_ls_wR_factor_gt          0.1461
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_restrained_S_all      0.924
_refine_ls_shift/su_max          0.004
_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 0.13555(13) 0.15266(11) 0.02199(14) 0.0485(4) Uani 1 1 d . . . . .
O2 O 0.31484(13) 0.13780(11) 0.19266(15) 0.0529(4) Uani 1 1 d . . . . .
O3 O 0.08775(13) 0.30907(11) -0.08656(13) 0.0463(4) Uani 1 1 d . . . . .
N2 N 0.10377(14) -0.14442(13) 0.14890(15) 0.0364(4) Uani 1 1 d . . . . .
N1 N 0.12840(16) 0.04189(14) 0.21215(16) 0.0403(4) Uani 1 1 d . . . . .
C1 C 0.24468(16) -0.03629(16) 0.05273(17) 0.0368(4) Uani 1 1 d . . . . .
C6 C 0.3282(2) -0.0378(2) -0.0281(2) 0.0548(6) Uani 1 1 d . . . . .
H6 H 0.3669 0.0307 -0.0427 0.066 Uiso 1 1 calc R U . . .
C5 C 0.3558(2) -0.1357(3) -0.0871(2) 0.0671(7) Uani 1 1 d . . . . .
H5 H 0.4126 -0.1335 -0.1409 0.081 Uiso 1 1 calc R U . . .
C4 C 0.3003(2) -0.2373(2) -0.0672(2) 0.0633(7) Uani 1 1 d . . . . .
H4 H 0.3191 -0.3045 -0.1075 0.076 Uiso 1 1 calc R U . . .
C3 C 0.2171(2) -0.2403(2) 0.0117(2) 0.0513(5) Uani 1 1 d . . . . .
H3 H 0.1793 -0.3093 0.0263 0.062 Uiso 1 1 calc R U . . .
C2 C 0.19007(16) -0.13973(16) 0.06950(17) 0.0350(4) Uani 1 1 d . . . . .
C7 C 0.07482(17) -0.05683(16) 0.21452(16) 0.0366(4) Uani 1 1 d . . . . .
C8 C -0.0214(2) -0.0749(2) 0.2911(2) 0.0565(6) Uani 1 1 d . . . . .
H8A H -0.0011 -0.0327 0.3704 0.085 Uiso 1 1 calc R U . . .
H8B H -0.0272 -0.1557 0.3094 0.085 Uiso 1 1 calc R U . . .
H8C H -0.0982 -0.0481 0.2431 0.085 Uiso 1 1 calc R U . . .
C9 C 0.33945(16) 0.24631(16) 0.16765(18) 0.0357(4) Uani 1 1 d . . . . .
C14 C 0.44040(18) 0.29834(18) 0.2425(2) 0.0453(5) Uani 1 1 d . . . . .
H14 H 0.4873 0.2581 0.3107 0.054 Uiso 1 1 calc R U . . .
C13 C 0.4709(2) 0.4079(2) 0.2163(2) 0.0540(6) Uani 1 1 d . . . . .
H13 H 0.5391 0.4422 0.2668 0.065 Uiso 1 1 calc R U . . .
C12 C 0.4034(2) 0.4685(2) 0.1172(2) 0.0664(7) Uani 1 1 d . . . . .
H12 H 0.4263 0.5431 0.0991 0.080 Uiso 1 1 calc R U . . .
C11 C 0.3021(2) 0.41944(19) 0.0449(2) 0.0574(6) Uani 1 1 d . . . . .
H11 H 0.2548 0.4612 -0.0218 0.069 Uiso 1 1 calc R U . . .
C10 C 0.26932(17) 0.30816(15) 0.06984(17) 0.0356(4) Uani 1 1 d . . . . .
C15 C 0.15923(17) 0.25714(16) -0.00359(17) 0.0354(4) Uani 1 1 d . . . . .
B1 B 0.2104(2) 0.07581(19) 0.1208(2) 0.0394(5) Uani 1 1 d . . . . .
H2 H 0.058(2) -0.2051(18) 0.144(2) 0.042(6) Uiso 1 1 d . . . . .
H1 H 0.110(2) 0.093(2) 0.262(2) 0.052(7) 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 C15 1.291(2) . ?
O1 B1 1.514(2) . ?
O2 C9 1.337(2) . ?
O2 B1 1.467(2) . ?
O3 C15 1.237(2) . ?
N2 C7 1.318(2) . ?
N2 C2 1.410(2) . ?
N2 H2 0.87(2) . ?
N1 C7 1.306(2) . ?
N1 B1 1.521(3) . ?
N1 H1 0.86(2) . ?
C1 C2 1.385(3) . ?
C1 C6 1.396(3) . ?
C1 B1 1.583(3) . ?
C6 C5 1.371(3) . ?
C6 H6 0.9400 . ?
C5 C4 1.379(4) . ?
C5 H5 0.9400 . ?
C4 C3 1.377(3) . ?
C4 H4 0.9400 . ?
C3 C2 1.389(3) . ?
C3 H3 0.9400 . ?
C7 C8 1.494(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C9 C10 1.387(3) . ?
C9 C14 1.398(3) . ?
C14 C13 1.370(3) . ?
C14 H14 0.9400 . ?
C13 C12 1.377(3) . ?
C13 H13 0.9400 . ?
C12 C11 1.375(3) . ?
C12 H12 0.9400 . ?
C11 C10 1.393(3) . ?
C11 H11 0.9400 . ?
C10 C15 1.462(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O1 B1 126.82(15) . . ?
C9 O2 B1 122.75(15) . . ?
C7 N2 C2 124.10(16) . . ?
C7 N2 H2 117.3(14) . . ?
C2 N2 H2 117.7(14) . . ?
C7 N1 B1 125.72(17) . . ?
C7 N1 H1 115.9(15) . . ?
B1 N1 H1 118.2(15) . . ?
C2 C1 C6 116.02(19) . . ?
C2 C1 B1 120.68(17) . . ?
C6 C1 B1 123.29(19) . . ?
C5 C6 C1 122.4(2) . . ?
C5 C6 H6 118.8 . . ?
C1 C6 H6 118.8 . . ?
C6 C5 C4 119.9(2) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C3 C2 119.0(2) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C1 C2 C3 122.75(18) . . ?
C1 C2 N2 119.16(17) . . ?
C3 C2 N2 118.08(18) . . ?
N1 C7 N2 120.96(18) . . ?
N1 C7 C8 121.54(19) . . ?
N2 C7 C8 117.50(18) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 C10 122.40(16) . . ?
O2 C9 C14 118.43(17) . . ?
C10 C9 C14 119.16(18) . . ?
C13 C14 C9 120.0(2) . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?
C14 C13 C12 121.0(2) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C11 C12 C13 119.6(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C9 C10 C11 119.88(18) . . ?
C9 C10 C15 119.57(16) . . ?
C11 C10 C15 120.51(18) . . ?
O3 C15 O1 118.94(17) . . ?
O3 C15 C10 123.57(17) . . ?
O1 C15 C10 117.47(16) . . ?
O2 B1 O1 110.79(15) . . ?
O2 B1 N1 108.59(17) . . ?
O1 B1 N1 106.06(16) . . ?
O2 B1 C1 114.07(17) . . ?
O1 B1 C1 108.86(16) . . ?
N1 B1 C1 108.14(16) . . ?

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
C2 C1 C6 C5 -0.5(3) . . . . ?
B1 C1 C6 C5 -179.4(2) . . . . ?
C1 C6 C5 C4 0.0(4) . . . . ?
C6 C5 C4 C3 0.0(4) . . . . ?
C5 C4 C3 C2 0.5(4) . . . . ?
C6 C1 C2 C3 1.0(3) . . . . ?
B1 C1 C2 C3 179.98(17) . . . . ?
C6 C1 C2 N2 -179.36(17) . . . . ?
B1 C1 C2 N2 -0.4(3) . . . . ?
C4 C3 C2 C1 -1.0(3) . . . . ?
C4 C3 C2 N2 179.34(19) . . . . ?
C7 N2 C2 C1 -3.4(3) . . . . ?
C7 N2 C2 C3 176.20(18) . . . . ?
B1 N1 C7 N2 11.3(3) . . . . ?
B1 N1 C7 C8 -168.59(18) . . . . ?
C2 N2 C7 N1 -1.8(3) . . . . ?
C2 N2 C7 C8 178.11(18) . . . . ?
B1 O2 C9 C10 -1.3(3) . . . . ?
B1 O2 C9 C14 179.29(19) . . . . ?
O2 C9 C14 C13 177.47(19) . . . . ?
C10 C9 C14 C13 -1.9(3) . . . . ?
C9 C14 C13 C12 0.2(3) . . . . ?
C14 C13 C12 C11 1.4(4) . . . . ?
C13 C12 C11 C10 -1.3(4) . . . . ?
O2 C9 C10 C11 -177.4(2) . . . . ?
C14 C9 C10 C11 2.0(3) . . . . ?
O2 C9 C10 C15 4.6(3) . . . . ?
C14 C9 C10 C15 -176.05(17) . . . . ?
C12 C11 C10 C9 -0.4(4) . . . . ?
C12 C11 C10 C15 177.6(2) . . . . ?
B1 O1 C15 O3 -179.13(19) . . . . ?
B1 O1 C15 C10 -0.2(3) . . . . ?
C9 C10 C15 O3 175.14(18) . . . . ?
C11 C10 C15 O3 -2.9(3) . . . . ?
C9 C10 C15 O1 -3.8(3) . . . . ?
C11 C10 C15 O1 178.2(2) . . . . ?
C9 O2 B1 O1 -2.3(3) . . . . ?
C9 O2 B1 N1 -118.36(19) . . . . ?
C9 O2 B1 C1 120.97(19) . . . . ?
C15 O1 B1 O2 3.1(3) . . . . ?
C15 O1 B1 N1 120.7(2) . . . . ?
C15 O1 B1 C1 -123.1(2) . . . . ?
C7 N1 B1 O2 -137.61(19) . . . . ?
C7 N1 B1 O1 103.3(2) . . . . ?
C7 N1 B1 C1 -13.3(2) . . . . ?
C2 C1 B1 O2 128.41(19) . . . . ?
C6 C1 B1 O2 -52.7(3) . . . . ?
C2 C1 B1 O1 -107.3(2) . . . . ?
C6 C1 B1 O1 71.6(2) . . . . ?
C2 C1 B1 N1 7.5(2) . . . . ?
C6 C1 B1 N1 -173.63(18) . . . . ?

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
N2 H2 O3 0.87(2) 2.04(2) 2.874(2) 159.2(19) 3
N1 H1 O3 0.86(2) 2.03(2) 2.874(2) 167(2) 4_566

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.038

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_1113th20
_database_code_depnum_ccdc_archive 'CCDC 1848683'
_audit_update_record             
;
2018-06-11 deposited with the CCDC.
2019-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 B2 N2 O3'
_chemical_formula_sum            'C15 H16 B2 N2 O3'
_chemical_formula_weight         293.92
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'

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'
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.3834(13)
_cell_length_b                   10.8026(9)
_cell_length_c                   12.7677(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.589(10)
_cell_angle_gamma                90
_cell_volume                     1526.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(1)
_cell_measurement_reflns_used    907
_cell_measurement_theta_min      3.6790
_cell_measurement_theta_max      29.0210

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.991

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.11347
_exptl_absorpt_correction_T_max  1.00000


_diffrn_ambient_temperature      173(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_detector_area_resol_mean 16.0774
_diffrn_measurement_method       'ω scans'

_diffrn_reflns_number            6288
_diffrn_reflns_av_unetI/netI     0.1112
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.283
_diffrn_reflns_theta_max         30.361
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4066
_reflns_number_gt                2170
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_cell_refinement       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_structure_solution    'SIR92 (Altomere, 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek, 2009)'



_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0704P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4066
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.0810
_refine_ls_wR_factor_ref         0.2174
_refine_ls_wR_factor_gt          0.1694
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.82404(17) 0.09370(17) 0.58468(12) 0.0339(5) Uani 1 1 d . . . . .
O21 O 0.79379(19) 0.30602(16) 0.56582(13) 0.0391(5) Uani 1 1 d . . . . .
O11 O 0.96757(18) -0.00242(18) 0.72543(13) 0.0399(5) Uani 1 1 d . . . . .
N2 N 0.7704(2) 0.2021(2) 0.26986(16) 0.0349(6) Uani 1 1 d . . . . .
N1 N 0.9003(2) 0.20256(19) 0.44046(15) 0.0311(5) Uani 1 1 d . . . . .
C1 C 1.0473(3) 0.1284(2) 0.59589(19) 0.0345(6) Uani 1 1 d . . . . .
C2 C 1.0237(2) 0.1972(2) 0.5005(2) 0.0319(6) Uani 1 1 d . . . . .
C12 C 0.5647(3) 0.1333(3) 0.4451(2) 0.0408(7) Uani 1 1 d . . . . .
H12 H 0.5648 0.1288 0.5194 0.049 Uiso 1 1 calc R U . . .
C7 C 0.6716(3) 0.1665(2) 0.41557(19) 0.0329(6) Uani 1 1 d . . . . .
C6 C 1.1676(3) 0.1156(3) 0.6513(2) 0.0408(7) Uani 1 1 d . . . . .
H6 H 1.1858 0.0703 0.7169 0.049 Uiso 1 1 calc R U . . .
C13 C 0.8777(3) 0.2098(2) 0.3345(2) 0.0323(6) Uani 1 1 d . . . . .
H13 H 0.9445 0.2215 0.3028 0.039 Uiso 1 1 calc R U . . .
C3 C 1.1168(3) 0.2560(3) 0.4654(2) 0.0403(7) Uani 1 1 d . . . . .
H3 H 1.0992 0.3070 0.4030 0.048 Uiso 1 1 calc R U . . .
C9 C 0.5594(3) 0.1474(3) 0.2276(2) 0.0454(8) Uani 1 1 d . . . . .
H9 H 0.5581 0.1529 0.1531 0.055 Uiso 1 1 calc R U . . .
C5 C 1.2607(3) 0.1663(3) 0.6142(3) 0.0465(8) Uani 1 1 d . . . . .
H5 H 1.3423 0.1516 0.6510 0.056 Uiso 1 1 calc R U . . .
C8 C 0.6651(3) 0.1731(2) 0.3055(2) 0.0337(6) Uani 1 1 d . . . . .
C4 C 1.2340(3) 0.2393(3) 0.5220(2) 0.0467(8) Uani 1 1 d . . . . .
H4 H 1.2978 0.2781 0.4979 0.056 Uiso 1 1 calc R U . . .
C11 C 0.4602(3) 0.1073(3) 0.3701(2) 0.0486(8) Uani 1 1 d . . . . .
H11 H 0.3895 0.0846 0.3928 0.058 Uiso 1 1 calc R U . . .
C10 C 0.4572(3) 0.1139(3) 0.2607(2) 0.0504(8) Uani 1 1 d . . . . .
H10 H 0.3847 0.0953 0.2089 0.061 Uiso 1 1 calc R U . . .
B1 B 0.9389(3) 0.0704(3) 0.6351(2) 0.0337(7) Uani 1 1 d . . . . .
B2 B 0.7949(3) 0.1915(3) 0.5027(2) 0.0331(7) Uani 1 1 d . . . . .
C14 C 0.8740(3) -0.0540(3) 0.7687(2) 0.0456(8) Uani 1 1 d . . . . .
H14A H 0.8155 0.0106 0.7744 0.068 Uiso 1 1 calc R U . . .
H14B H 0.9089 -0.0883 0.8403 0.068 Uiso 1 1 calc R U . . .
H14C H 0.8332 -0.1200 0.7211 0.068 Uiso 1 1 calc R U . . .
C15 C 0.7687(4) 0.4195(3) 0.5116(2) 0.0643(11) Uani 1 1 d . . . . .
H15A H 0.8393 0.4462 0.4860 0.096 Uiso 1 1 calc R U . . .
H15B H 0.7498 0.4818 0.5610 0.096 Uiso 1 1 calc R U . . .
H15C H 0.6993 0.4097 0.4501 0.096 Uiso 1 1 calc R U . . .
H2 H 0.766(3) 0.205(3) 0.192(3) 0.077 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 B1 1.339(4) . ?
O1 B2 1.470(3) . ?
O21 C15 1.404(3) . ?
O21 B2 1.478(3) . ?
O11 B1 1.370(3) . ?
O11 C14 1.424(3) . ?
N2 C13 1.306(4) . ?
N2 C8 1.414(3) . ?
N2 H2 0.99(3) . ?
N1 C13 1.319(3) . ?
N1 C2 1.434(4) . ?
N1 B2 1.591(4) . ?
C1 C6 1.392(4) . ?
C1 C2 1.398(4) . ?
C1 B1 1.568(4) . ?
C2 C3 1.397(4) . ?
C12 C11 1.370(4) . ?
C12 C7 1.403(4) . ?
C12 H12 0.9500 . ?
C7 C8 1.392(3) . ?
C7 B2 1.596(4) . ?
C6 C5 1.373(4) . ?
C6 H6 0.9500 . ?
C13 H13 0.9500 . ?
C3 C4 1.372(4) . ?
C3 H3 0.9500 . ?
C9 C10 1.377(4) . ?
C9 C8 1.397(4) . ?
C9 H9 0.9500 . ?
C5 C4 1.390(4) . ?
C5 H5 0.9500 . ?
C4 H4 0.9500 . ?
C11 C10 1.390(4) . ?
C11 H11 0.9500 . ?
C10 H10 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
B1 O1 B2 120.6(2) . . ?
C15 O21 B2 119.3(2) . . ?
B1 O11 C14 120.0(2) . . ?
C13 N2 C8 123.3(2) . . ?
C13 N2 H2 117(2) . . ?
C8 N2 H2 119(2) . . ?
C13 N1 C2 118.8(2) . . ?
C13 N1 B2 121.9(2) . . ?
C2 N1 B2 119.26(19) . . ?
C6 C1 C2 117.4(3) . . ?
C6 C1 B1 123.5(2) . . ?
C2 C1 B1 119.1(3) . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 N1 122.1(2) . . ?
C1 C2 N1 116.8(2) . . ?
C11 C12 C7 122.0(2) . . ?
C11 C12 H12 119.0 . . ?
C7 C12 H12 119.0 . . ?
C8 C7 C12 116.2(3) . . ?
C8 C7 B2 121.6(2) . . ?
C12 C7 B2 122.2(2) . . ?
C5 C6 C1 122.1(3) . . ?
C5 C6 H6 118.9 . . ?
C1 C6 H6 118.9 . . ?
N2 C13 N1 124.9(3) . . ?
N2 C13 H13 117.5 . . ?
N1 C13 H13 117.5 . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C10 C9 C8 118.8(2) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C7 C8 C9 122.8(3) . . ?
C7 C8 N2 119.2(3) . . ?
C9 C8 N2 117.9(2) . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C9 C10 C11 119.9(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
O1 B1 O11 121.7(3) . . ?
O1 B1 C1 121.6(2) . . ?
O11 B1 C1 116.6(3) . . ?
O1 B2 O21 104.02(19) . . ?
O1 B2 N1 109.8(2) . . ?
O21 B2 N1 108.3(2) . . ?
O1 B2 C7 112.9(2) . . ?
O21 B2 C7 113.8(2) . . ?
N1 B2 C7 107.94(19) . . ?
O11 C14 H14A 109.5 . . ?
O11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O21 C15 H15A 109.5 . . ?
O21 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O21 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -3.3(4) . . . . ?
B1 C1 C2 C3 176.6(2) . . . . ?
C6 C1 C2 N1 175.8(2) . . . . ?
B1 C1 C2 N1 -4.2(3) . . . . ?
C13 N1 C2 C3 31.6(4) . . . . ?
B2 N1 C2 C3 -152.0(2) . . . . ?
C13 N1 C2 C1 -147.5(2) . . . . ?
B2 N1 C2 C1 28.9(3) . . . . ?
C11 C12 C7 C8 0.8(4) . . . . ?
C11 C12 C7 B2 -177.4(3) . . . . ?
C2 C1 C6 C5 -0.9(4) . . . . ?
B1 C1 C6 C5 179.2(3) . . . . ?
C8 N2 C13 N1 -6.2(4) . . . . ?
C2 N1 C13 N2 172.4(2) . . . . ?
B2 N1 C13 N2 -3.9(4) . . . . ?
C1 C2 C3 C4 4.2(4) . . . . ?
N1 C2 C3 C4 -174.9(2) . . . . ?
C1 C6 C5 C4 4.1(4) . . . . ?
C12 C7 C8 C9 -0.5(4) . . . . ?
B2 C7 C8 C9 177.7(3) . . . . ?
C12 C7 C8 N2 -178.0(2) . . . . ?
B2 C7 C8 N2 0.3(4) . . . . ?
C10 C9 C8 C7 -0.1(5) . . . . ?
C10 C9 C8 N2 177.3(3) . . . . ?
C13 N2 C8 C7 8.0(4) . . . . ?
C13 N2 C8 C9 -169.6(3) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C6 C5 C4 C3 -3.2(5) . . . . ?
C7 C12 C11 C10 -0.4(5) . . . . ?
C8 C9 C10 C11 0.6(5) . . . . ?
C12 C11 C10 C9 -0.3(5) . . . . ?
B2 O1 B1 O11 167.1(2) . . . . ?
B2 O1 B1 C1 -10.9(4) . . . . ?
C14 O11 B1 O1 -0.8(4) . . . . ?
C14 O11 B1 C1 177.3(2) . . . . ?
C6 C1 B1 O1 174.1(3) . . . . ?
C2 C1 B1 O1 -5.8(4) . . . . ?
C6 C1 B1 O11 -4.0(4) . . . . ?
C2 C1 B1 O11 176.1(2) . . . . ?
B1 O1 B2 O21 -83.4(3) . . . . ?
B1 O1 B2 N1 32.3(3) . . . . ?
B1 O1 B2 C7 152.8(2) . . . . ?
C15 O21 B2 O1 179.9(3) . . . . ?
C15 O21 B2 N1 63.1(4) . . . . ?
C15 O21 B2 C7 -56.9(4) . . . . ?
C13 N1 B2 O1 133.7(2) . . . . ?
C2 N1 B2 O1 -42.6(3) . . . . ?
C13 N1 B2 O21 -113.4(3) . . . . ?
C2 N1 B2 O21 70.4(3) . . . . ?
C13 N1 B2 C7 10.2(3) . . . . ?
C2 N1 B2 C7 -166.0(2) . . . . ?
C8 C7 B2 O1 -129.8(2) . . . . ?
C12 C7 B2 O1 48.4(3) . . . . ?
C8 C7 B2 O21 112.0(3) . . . . ?
C12 C7 B2 O21 -69.9(3) . . . . ?
C8 C7 B2 N1 -8.2(3) . . . . ?
C12 C7 B2 N1 169.9(2) . . . . ?

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
N2 H2 O21 0.99(3) 1.71(4) 2.682(2) 166(3) 4_565

_refine_diff_density_max         0.325
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.067

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_1118th21
_database_code_depnum_ccdc_archive 'CCDC 1848684'
_audit_update_record             
;
2018-06-11 deposited with the CCDC.
2019-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014



_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H13 B N2 O2, H2 O'
_chemical_formula_sum            'C14 H15 B N2 O3'
_chemical_formula_weight         270.09
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'


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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.0763(5)
_cell_length_b                   9.3343(7)
_cell_length_c                   20.5929(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.821(7)
_cell_angle_gamma                90
_cell_volume                     1358.56(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    2085
_cell_measurement_theta_min      3.7850
_cell_measurement_theta_max      30.5260

_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.340
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.97017
_exptl_absorpt_correction_T_max  1.00000

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_detector_area_resol_mean 16.0774
_diffrn_measurement_method       'ω scans'

_diffrn_reflns_number            8052
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.416
_diffrn_reflns_theta_max         30.847
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3760
_reflns_number_gt                2877
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_cell_refinement       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_structure_solution    'SIR92 (Altomere, 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek, 2009)'


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1707P)²+1.4463P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3760
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1853
_refine_ls_wR_factor_gt          0.1541
_refine_ls_goodness_of_fit_ref   0.653
_refine_ls_restrained_S_all      0.653
_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 0.11013(16) 0.25991(14) 0.13804(6) 0.0318(3) Uani 1 1 d . . . . .
O2 O 0.43360(15) 0.30944(13) 0.12562(6) 0.0309(3) Uani 1 1 d . . . . .
O3 O -0.2324(2) 0.27952(15) 0.06136(8) 0.0412(3) Uani 1 1 d . . . . .
N2 N 0.26308(19) -0.03828(14) 0.01571(7) 0.0277(3) Uani 1 1 d . . . . .
N1 N 0.3266(2) 0.05559(16) 0.11726(7) 0.0323(3) Uani 1 1 d . . . . .
C11 C 0.1556(4) 0.5564(2) 0.25537(9) 0.0484(5) Uani 1 1 d . . . . .
H11 H 0.0864 0.6117 0.2848 0.058 Uiso 1 1 calc R U . . .
C7 C 0.1702(2) 0.36904(18) 0.17781(7) 0.0294(3) Uani 1 1 d . . . . .
C2 C 0.2250(2) 0.09593(16) -0.01407(7) 0.0248(3) Uani 1 1 d . . . . .
C8 C 0.3606(2) 0.39873(17) 0.17027(7) 0.0289(3) Uani 1 1 d . . . . .
C1 C 0.2349(2) 0.22047(16) 0.02346(7) 0.0250(3) Uani 1 1 d . . . . .
C13 C 0.3130(2) -0.05494(17) 0.07766(8) 0.0283(3) Uani 1 1 d . . . . .
C3 C 0.1795(2) 0.09803(19) -0.08105(8) 0.0314(4) Uani 1 1 d . . . . .
H3 H 0.1735 0.0115 -0.1053 0.038 Uiso 1 1 calc R U . . .
C12 C 0.0646(3) 0.4457(2) 0.22044(8) 0.0399(4) Uani 1 1 d . . . . .
H12 H -0.0649 0.4241 0.2258 0.048 Uiso 1 1 calc R U . . .
C10 C 0.3437(4) 0.5865(2) 0.24790(9) 0.0491(6) Uani 1 1 d . . . . .
H10 H 0.4019 0.6623 0.2723 0.059 Uiso 1 1 calc R U . . .
C9 C 0.4513(3) 0.50737(19) 0.20487(9) 0.0393(4) Uani 1 1 d . . . . .
H9 H 0.5813 0.5279 0.1998 0.047 Uiso 1 1 calc R U . . .
C6 C 0.1989(2) 0.34983(17) -0.00920(8) 0.0314(3) Uani 1 1 d . . . . .
H6 H 0.2059 0.4369 0.0147 0.038 Uiso 1 1 calc R U . . .
C14 C 0.3520(3) -0.20382(19) 0.10163(11) 0.0402(4) Uani 1 1 d . . . . .
H14A H 0.4400 -0.2003 0.1399 0.060 Uiso 1 1 calc R U . . .
H14B H 0.4082 -0.2599 0.0673 0.060 Uiso 1 1 calc R U . . .
H14C H 0.2334 -0.2488 0.1135 0.060 Uiso 1 1 calc R U . . .
C5 C 0.1534(3) 0.3544(2) -0.07552(9) 0.0366(4) Uani 1 1 d . . . . .
H5 H 0.1291 0.4436 -0.0965 0.044 Uiso 1 1 calc R U . . .
C4 C 0.1434(3) 0.2280(2) -0.11118(8) 0.0357(4) Uani 1 1 d . . . . .
H4 H 0.1117 0.2310 -0.1565 0.043 Uiso 1 1 calc R U . . .
B1 B 0.2769(2) 0.21239(19) 0.09995(8) 0.0262(3) Uani 1 1 d . . . . .
H2 H 0.253(3) -0.117(3) -0.0094(11) 0.038(6) Uiso 1 1 d . . . . .
H1 H 0.365(4) 0.029(3) 0.1571(13) 0.054(7) Uiso 1 1 d . . . . .
H32 H -0.328(5) 0.294(3) 0.0850(16) 0.073(9) Uiso 1 1 d . . . . .
H31 H -0.132(5) 0.276(3) 0.0892(15) 0.068(9) 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 C7 1.362(2) . ?
O1 B1 1.515(2) . ?
O2 C8 1.3615(19) . ?
O2 B1 1.507(2) . ?
O3 H32 0.86(4) . ?
O3 H31 0.89(3) . ?
N2 C13 1.316(2) . ?
N2 C2 1.415(2) . ?
N2 H2 0.90(2) . ?
N1 C13 1.316(2) . ?
N1 B1 1.543(2) . ?
N1 H1 0.89(3) . ?
C11 C10 1.376(4) . ?
C11 C12 1.398(3) . ?
C11 H11 0.9500 . ?
C7 C12 1.381(2) . ?
C7 C8 1.391(2) . ?
C2 C1 1.396(2) . ?
C2 C3 1.401(2) . ?
C8 C9 1.380(2) . ?
C1 C6 1.399(2) . ?
C1 B1 1.590(2) . ?
C13 C14 1.496(2) . ?
C3 C4 1.381(2) . ?
C3 H3 0.9500 . ?
C12 H12 0.9500 . ?
C10 C9 1.406(3) . ?
C10 H10 0.9500 . ?
C9 H9 0.9500 . ?
C6 C5 1.388(2) . ?
C6 H6 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C5 C4 1.389(3) . ?
C5 H5 0.9500 . ?
C4 H4 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
C7 O1 B1 107.58(12) . . ?
C8 O2 B1 107.93(12) . . ?
H32 O3 H31 105(3) . . ?
C13 N2 C2 124.13(14) . . ?
C13 N2 H2 118.0(14) . . ?
C2 N2 H2 117.9(14) . . ?
C13 N1 B1 126.28(14) . . ?
C13 N1 H1 111.1(17) . . ?
B1 N1 H1 122.6(17) . . ?
C10 C11 C12 121.14(18) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
O1 C7 C12 127.38(17) . . ?
O1 C7 C8 110.93(13) . . ?
C12 C7 C8 121.69(17) . . ?
C1 C2 C3 122.43(14) . . ?
C1 C2 N2 119.62(13) . . ?
C3 C2 N2 117.95(14) . . ?
O2 C8 C9 128.04(17) . . ?
O2 C8 C7 110.80(14) . . ?
C9 C8 C7 121.15(16) . . ?
C2 C1 C6 116.72(14) . . ?
C2 C1 B1 120.71(13) . . ?
C6 C1 B1 122.52(14) . . ?
N1 C13 N2 121.07(14) . . ?
N1 C13 C14 121.15(16) . . ?
N2 C13 C14 117.77(15) . . ?
C4 C3 C2 118.89(15) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C7 C12 C11 117.39(19) . . ?
C7 C12 H12 121.3 . . ?
C11 C12 H12 121.3 . . ?
C11 C10 C9 121.33(18) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C8 C9 C10 117.3(2) . . ?
C8 C9 H9 121.3 . . ?
C10 C9 H9 121.3 . . ?
C5 C6 C1 121.80(15) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C6 C5 C4 119.82(16) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C3 C4 C5 120.34(15) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
O2 B1 O1 102.75(12) . . ?
O2 B1 N1 109.50(13) . . ?
O1 B1 N1 109.42(13) . . ?
O2 B1 C1 114.67(13) . . ?
O1 B1 C1 112.72(13) . . ?
N1 B1 C1 107.65(13) . . ?

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
B1 O1 C7 C12 179.05(16) . . . . ?
B1 O1 C7 C8 -0.24(17) . . . . ?
C13 N2 C2 C1 -1.7(2) . . . . ?
C13 N2 C2 C3 177.89(14) . . . . ?
B1 O2 C8 C9 -178.19(16) . . . . ?
B1 O2 C8 C7 1.04(17) . . . . ?
O1 C7 C8 O2 -0.52(18) . . . . ?
C12 C7 C8 O2 -179.85(14) . . . . ?
O1 C7 C8 C9 178.77(14) . . . . ?
C12 C7 C8 C9 -0.6(2) . . . . ?
C3 C2 C1 C6 -0.7(2) . . . . ?
N2 C2 C1 C6 178.90(14) . . . . ?
C3 C2 C1 B1 176.89(14) . . . . ?
N2 C2 C1 B1 -3.5(2) . . . . ?
B1 N1 C13 N2 4.1(3) . . . . ?
B1 N1 C13 C14 -175.40(15) . . . . ?
C2 N2 C13 N1 1.6(2) . . . . ?
C2 N2 C13 C14 -178.86(14) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
N2 C2 C3 C4 -179.44(15) . . . . ?
O1 C7 C12 C11 -178.37(16) . . . . ?
C8 C7 C12 C11 0.9(2) . . . . ?
C10 C11 C12 C7 -0.6(3) . . . . ?
C12 C11 C10 C9 0.0(3) . . . . ?
O2 C8 C9 C10 179.15(15) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
C11 C10 C9 C8 0.3(3) . . . . ?
C2 C1 C6 C5 0.8(2) . . . . ?
B1 C1 C6 C5 -176.80(16) . . . . ?
C1 C6 C5 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C6 C5 C4 C3 -0.3(3) . . . . ?
C8 O2 B1 O1 -1.10(16) . . . . ?
C8 O2 B1 N1 -117.32(14) . . . . ?
C8 O2 B1 C1 121.57(14) . . . . ?
C7 O1 B1 O2 0.80(16) . . . . ?
C7 O1 B1 N1 117.07(13) . . . . ?
C7 O1 B1 C1 -123.17(14) . . . . ?
C13 N1 B1 O2 -133.35(16) . . . . ?
C13 N1 B1 O1 114.74(17) . . . . ?
C13 N1 B1 C1 -8.1(2) . . . . ?
C2 C1 B1 O2 129.56(15) . . . . ?
C6 C1 B1 O2 -53.0(2) . . . . ?
C2 C1 B1 O1 -113.33(16) . . . . ?
C6 C1 B1 O1 64.1(2) . . . . ?
C2 C1 B1 N1 7.4(2) . . . . ?
C6 C1 B1 N1 -175.10(14) . . . . ?

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
N2 H2 O3 0.90(2) 1.86(2) 2.7573(19) 180(2) 3
O3 H32 O2 0.86(4) 1.92(4) 2.7792(19) 170(3) 1_455
O3 H31 O1 0.89(3) 1.95(3) 2.8327(19) 171(3) .

_refine_diff_density_max         0.389
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.046

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_1122th23
_database_code_depnum_ccdc_archive 'CCDC 1848685'
_audit_update_record             
;
2018-06-11 deposited with the CCDC.
2019-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014


_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 B N2 O4'
_chemical_formula_sum            'C17 H17 B N2 O4'
_chemical_formula_weight         324.13
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 3-methoxypropionitrile'

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'
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.4042(11)
_cell_length_b                   9.1650(5)
_cell_length_c                   13.2350(9)
_cell_angle_alpha                90
_cell_angle_beta                 113.504(8)
_cell_angle_gamma                90
_cell_volume                     1602.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    2245
_cell_measurement_theta_min      3.5390
_cell_measurement_theta_max      29.9770

_exptl_crystal_description       block
_exptl_crystal_colour            'pale brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_T_min  0.97715
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_detector_area_resol_mean 16.0774
_diffrn_measurement_method       'ω scans'

_diffrn_reflns_number            10442
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.357
_diffrn_reflns_theta_max         30.791
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4470
_reflns_number_gt                3341
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_cell_refinement       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1058P)²+4.1734P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4470
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1521
_refine_ls_wR_factor_gt          0.1240
_refine_ls_goodness_of_fit_ref   0.583
_refine_ls_restrained_S_all      0.583
_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 0.69853(10) 0.46352(13) 0.36059(9) 0.0285(3) Uani 1 1 d . . . . .
O3 O 0.73919(10) 0.63394(13) 0.24149(9) 0.0303(3) Uani 1 1 d . . . . .
O2 O 0.68154(11) 0.53933(14) 0.50969(10) 0.0338(3) Uani 1 1 d . . . . .
O4 O 0.54973(10) 0.40714(15) -0.11877(10) 0.0356(3) Uani 1 1 d . . . . .
N1 N 0.62970(11) 0.42522(16) 0.16253(11) 0.0260(3) Uani 1 1 d . . . . .
N2 N 0.70655(11) 0.23242(16) 0.11663(11) 0.0260(3) Uani 1 1 d . . . . .
C14 C 0.62491(12) 0.31006(18) 0.10261(12) 0.0243(3) Uani 1 1 d . . . . .
C8 C 0.80438(12) 0.26602(18) 0.19546(13) 0.0248(3) Uani 1 1 d . . . . .
C2 C 0.76076(12) 0.73452(17) 0.32154(12) 0.0242(3) Uani 1 1 d . . . . .
C9 C 0.81657(12) 0.37970(18) 0.26915(13) 0.0261(3) Uani 1 1 d . . . . .
C13 C 0.88550(14) 0.1823(2) 0.19613(16) 0.0338(4) Uani 1 1 d . . . . .
H13 H 0.8750 0.1069 0.1434 0.041 Uiso 1 1 calc R U . . .
C1 C 0.74117(12) 0.70994(17) 0.41550(12) 0.0230(3) Uani 1 1 d . . . . .
C7 C 0.70466(12) 0.56614(18) 0.43190(12) 0.0232(3) Uani 1 1 d . . . . .
C17 C 0.57097(19) 0.4157(3) -0.21476(18) 0.0565(7) Uani 1 1 d . . . . .
H17A H 0.6283 0.3520 -0.2060 0.085 Uiso 1 1 calc R U . . .
H17B H 0.5879 0.5166 -0.2253 0.085 Uiso 1 1 calc R U . . .
H17C H 0.5114 0.3845 -0.2791 0.085 Uiso 1 1 calc R U . . .
C15 C 0.52526(13) 0.2616(2) 0.01570(14) 0.0316(4) Uani 1 1 d . . . . .
H15A H 0.4710 0.3266 0.0174 0.038 Uiso 1 1 calc R U . . .
H15B H 0.5103 0.1615 0.0329 0.038 Uiso 1 1 calc R U . . .
C3 C 0.80233(16) 0.8678(2) 0.30966(16) 0.0354(4) Uani 1 1 d . . . . .
H3 H 0.8158 0.8863 0.2462 0.043 Uiso 1 1 calc R U . . .
C16 C 0.52452(14) 0.2635(2) -0.09864(14) 0.0345(4) Uani 1 1 d . . . . .
H16A H 0.5745 0.1930 -0.1037 0.041 Uiso 1 1 calc R U . . .
H16B H 0.4567 0.2364 -0.1537 0.041 Uiso 1 1 calc R U . . .
C6 C 0.76089(14) 0.81946(19) 0.49502(14) 0.0307(4) Uani 1 1 d . . . . .
H6 H 0.7455 0.8036 0.5576 0.037 Uiso 1 1 calc R U . . .
C10 C 0.91488(15) 0.4045(2) 0.34717(17) 0.0404(5) Uani 1 1 d . . . . .
H10 H 0.9264 0.4811 0.3992 0.048 Uiso 1 1 calc R U . . .
C5 C 0.80235(17) 0.9499(2) 0.48299(16) 0.0396(4) Uani 1 1 d . . . . .
H5 H 0.8163 1.0239 0.5373 0.048 Uiso 1 1 calc R U . . .
C12 C 0.98126(15) 0.2104(3) 0.2745(2) 0.0452(5) Uani 1 1 d . . . . .
H12 H 1.0372 0.1541 0.2762 0.054 Uiso 1 1 calc R U . . .
C4 C 0.82374(18) 0.9726(2) 0.39076(17) 0.0416(5) Uani 1 1 d . . . . .
H4 H 0.8537 1.0621 0.3833 0.050 Uiso 1 1 calc R U . . .
B1 B 0.72359(14) 0.4795(2) 0.26069(14) 0.0243(3) Uani 1 1 d . . . . .
C11 C 0.99566(16) 0.3206(3) 0.3506(2) 0.0514(6) Uani 1 1 d . . . . .
H11 H 1.0614 0.3386 0.4054 0.062 Uiso 1 1 calc R U . . .
H1 H 0.5700(16) 0.470(2) 0.1451(17) 0.032(5) Uiso 1 1 d . . . . .
H2 H 0.6978(17) 0.153(3) 0.0790(19) 0.036(6) 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 C7 1.3102(19) . ?
O1 B1 1.510(2) . ?
O3 C2 1.3441(19) . ?
O3 B1 1.471(2) . ?
O2 C7 1.2267(19) . ?
O4 C16 1.419(2) . ?
O4 C17 1.423(2) . ?
N1 C14 1.305(2) . ?
N1 B1 1.537(2) . ?
N1 H1 0.90(2) . ?
N2 C14 1.323(2) . ?
N2 C8 1.413(2) . ?
N2 H2 0.87(2) . ?
C14 C15 1.505(2) . ?
C8 C9 1.390(2) . ?
C8 C13 1.395(2) . ?
C2 C3 1.397(2) . ?
C2 C1 1.399(2) . ?
C9 C10 1.399(2) . ?
C9 B1 1.588(2) . ?
C13 C12 1.380(3) . ?
C13 H13 0.9500 . ?
C1 C6 1.399(2) . ?
C1 C7 1.467(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C15 C16 1.509(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C6 C5 1.373(3) . ?
C6 H6 0.9500 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9500 . ?
C5 C4 1.389(3) . ?
C5 H5 0.9500 . ?
C12 C11 1.381(3) . ?
C12 H12 0.9500 . ?
C4 H4 0.9500 . ?
C11 H11 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
C7 O1 B1 126.16(13) . . ?
C2 O3 B1 121.80(12) . . ?
C16 O4 C17 112.40(17) . . ?
C14 N1 B1 126.20(14) . . ?
C14 N1 H1 113.7(14) . . ?
B1 N1 H1 120.0(14) . . ?
C14 N2 C8 123.74(14) . . ?
C14 N2 H2 117.1(15) . . ?
C8 N2 H2 118.9(15) . . ?
N1 C14 N2 121.40(15) . . ?
N1 C14 C15 120.41(15) . . ?
N2 C14 C15 118.18(15) . . ?
C9 C8 C13 122.48(16) . . ?
C9 C8 N2 119.43(14) . . ?
C13 C8 N2 118.09(15) . . ?
O3 C2 C3 119.07(14) . . ?
O3 C2 C1 121.68(14) . . ?
C3 C2 C1 119.24(15) . . ?
C8 C9 C10 116.57(16) . . ?
C8 C9 B1 121.01(14) . . ?
C10 C9 B1 122.36(15) . . ?
C12 C13 C8 119.03(18) . . ?
C12 C13 H13 120.5 . . ?
C8 C13 H13 120.5 . . ?
C2 C1 C6 120.05(15) . . ?
C2 C1 C7 119.18(14) . . ?
C6 C1 C7 120.70(14) . . ?
O2 C7 O1 119.86(15) . . ?
O2 C7 C1 122.51(15) . . ?
O1 C7 C1 117.62(13) . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C15 C16 112.72(15) . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C4 C3 C2 119.60(16) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
O4 C16 C15 107.40(14) . . ?
O4 C16 H16A 110.2 . . ?
C15 C16 H16A 110.2 . . ?
O4 C16 H16B 110.2 . . ?
C15 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
C5 C6 C1 120.29(16) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C11 C10 C9 121.68(19) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C6 C5 C4 119.46(17) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C13 C12 C11 119.94(19) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C3 C4 C5 121.32(18) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
O3 B1 O1 110.54(13) . . ?
O3 B1 N1 107.99(14) . . ?
O1 B1 N1 105.77(13) . . ?
O3 B1 C9 112.55(14) . . ?
O1 B1 C9 111.82(13) . . ?
N1 B1 C9 107.83(13) . . ?
C10 C11 C12 120.26(19) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?

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
B1 N1 C14 N2 -5.5(3) . . . . ?
B1 N1 C14 C15 174.08(15) . . . . ?
C8 N2 C14 N1 -0.3(2) . . . . ?
C8 N2 C14 C15 -179.84(15) . . . . ?
C14 N2 C8 C9 5.2(2) . . . . ?
C14 N2 C8 C13 -175.02(16) . . . . ?
B1 O3 C2 C3 162.11(17) . . . . ?
B1 O3 C2 C1 -18.9(2) . . . . ?
C13 C8 C9 C10 -1.6(3) . . . . ?
N2 C8 C9 C10 178.15(16) . . . . ?
C13 C8 C9 B1 175.82(16) . . . . ?
N2 C8 C9 B1 -4.4(2) . . . . ?
C9 C8 C13 C12 1.7(3) . . . . ?
N2 C8 C13 C12 -178.08(17) . . . . ?
O3 C2 C1 C6 -177.44(16) . . . . ?
C3 C2 C1 C6 1.5(2) . . . . ?
O3 C2 C1 C7 5.6(2) . . . . ?
C3 C2 C1 C7 -175.47(16) . . . . ?
B1 O1 C7 O2 179.64(15) . . . . ?
B1 O1 C7 C1 -1.3(2) . . . . ?
C2 C1 C7 O2 -176.51(16) . . . . ?
C6 C1 C7 O2 6.5(2) . . . . ?
C2 C1 C7 O1 4.5(2) . . . . ?
C6 C1 C7 O1 -172.49(15) . . . . ?
N1 C14 C15 C16 118.68(18) . . . . ?
N2 C14 C15 C16 -61.7(2) . . . . ?
O3 C2 C3 C4 179.27(18) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C17 O4 C16 C15 168.37(16) . . . . ?
C14 C15 C16 O4 -56.69(19) . . . . ?
C2 C1 C6 C5 -2.0(3) . . . . ?
C7 C1 C6 C5 175.00(17) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
B1 C9 C10 C11 -177.3(2) . . . . ?
C1 C6 C5 C4 0.6(3) . . . . ?
C8 C13 C12 C11 -0.2(3) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
C6 C5 C4 C3 1.3(3) . . . . ?
C2 O3 B1 O1 20.0(2) . . . . ?
C2 O3 B1 N1 135.28(15) . . . . ?
C2 O3 B1 C9 -105.81(17) . . . . ?
C7 O1 B1 O3 -10.1(2) . . . . ?
C7 O1 B1 N1 -126.72(16) . . . . ?
C7 O1 B1 C9 116.16(17) . . . . ?
C14 N1 B1 O3 127.32(16) . . . . ?
C14 N1 B1 O1 -114.32(17) . . . . ?
C14 N1 B1 C9 5.5(2) . . . . ?
C8 C9 B1 O3 -119.33(17) . . . . ?
C10 C9 B1 O3 58.0(2) . . . . ?
C8 C9 B1 O1 115.53(16) . . . . ?
C10 C9 B1 O1 -67.2(2) . . . . ?
C8 C9 B1 N1 -0.3(2) . . . . ?
C10 C9 B1 N1 176.98(16) . . . . ?
C9 C10 C11 C12 1.3(4) . . . . ?
C13 C12 C11 C10 -1.2(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
C16 H16A O1 0.99 2.48 3.462(2) 171.9 4_565
N1 H1 O4 0.90(2) 1.97(2) 2.8604(19) 172(2) 3_665
N2 H2 O2 0.87(2) 1.95(2) 2.8159(19) 174(2) 4_565

_refine_diff_density_max         0.321
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.043

_shelxl_version_number           2014-3



