# Electronic Supplementary Material (ESI) for Chemical Communications.
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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_neummi805

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 B2 N2 O'
_chemical_formula_weight         370.01

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'
N N 0.0311 0.0180 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   5.2893(3)
_cell_length_b                   15.6927(8)
_cell_length_c                   20.2458(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1680.47(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    116
_cell_measurement_theta_min      27.00
_cell_measurement_theta_max      53.5

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    0.691
_shelx_estimated_absorpt_T_min   0.877
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_T_max  0.9450
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Imus-focus sealed tube'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'SMART APEX II DUO'
_diffrn_measurement_method       'omega/phi scans'
_diffrn_reflns_number            17542
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.563
_diffrn_reflns_theta_max         66.624
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             2950
_reflns_number_gt                2710
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_max     0.984
_reflns_Friedel_fraction_full    0.961

_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       COSMO
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 The structure shows a disorder in the B ans N Atoms Of the borazine
 and this causes also a disorder of the O-H group bonded to the boron.
 The Measurement has been carried out with Cu radiation, and this
 leads on a fixed Chi geometrie to an incompleteness of the data,
 Poor Data / Parameter Ratio and Missing # FCF.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0592P)²+0.1249P] 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_abs_structure_details 
;
 Flack x determined using 1037 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.12(18)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2950
_refine_ls_number_parameters     288
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0939
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.042
_refine_ls_shift/su_mean         0.002

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
O1A O 0.8901(2) 0.46133(7) 0.84669(5) 0.0371(3) Uani 0.3321(7) 1 d . . P A 1
H1AA H 0.917(4) 0.4941(13) 0.8801(10) 0.048(5) Uiso 0.3321(7) 1 d . . P A 1
O1B O 1.05554(12) 0.45513(4) 0.79035(3) 0.03622(15) Uani 0.6679(7) 1 d . . P A
2
H2AA H 1.172(2) 0.4899(6) 0.7873(5) 0.044(3) Uiso 0.6679(7) 1 d . . P A 2
N1 N 0.70089(10) 0.38881(3) 0.86000(2) 0.03406(14) Uani 0.6569(17) 1 d . . P A
1
N2 N 0.85628(9) 0.32691(3) 0.75162(2) 0.02786(12) Uani 0.6569(17) 1 d . . P A 1
B1 B 1.04743(10) 0.39070(3) 0.74153(3) 0.03024(14) Uani 0.6569(17) 1 d . . P A
1
B2 B 0.68749(10) 0.32850(3) 0.80884(3) 0.03062(14) Uani 0.6569(17) 1 d . . P A
1
H1A H 0.8166(16) 0.4265(5) 0.8610(4) 0.0194(19) Uiso 0.6569(17) 1 d . . P A 1
N11 N 1.04743(10) 0.39070(3) 0.74153(3) 0.03024(14) Uani 0.3431(17) 1 d D . P A
2
N12 N 0.68749(10) 0.32850(3) 0.80884(3) 0.03062(14) Uani 0.3431(17) 1 d . . P A
2
B11 B 0.70089(10) 0.38881(3) 0.86000(2) 0.03406(14) Uani 0.3431(17) 1 d . . P A
2
B12 B 0.85628(9) 0.32691(3) 0.75162(2) 0.02786(12) Uani 0.3431(17) 1 d . . P A
2
H1B H 1.098(3) 0.4382(6) 0.7665(6) 0.033 Uiso 0.3431(17) 1 d D U P A 2
C1 C 0.53276(11) 0.39131(4) 0.91567(3) 0.03560(15) Uani 1 1 d . . . . .
C2 C 0.33850(11) 0.32980(4) 0.92016(3) 0.03481(14) Uani 1 1 d . . . . .
C3 C 0.17024(12) 0.33653(4) 0.97387(3) 0.04058(16) Uani 1 1 d . . . . .
H3 H 0.0384 0.2958 0.9781 0.049 Uiso 1 1 calc R U . . .
C4 C 0.19061(12) 0.39987(4) 1.02013(3) 0.04220(16) Uani 1 1 d . . . . .
H4 H 0.0714 0.4032 1.0551 0.051 Uiso 1 1 calc R U . . .
C5 C 0.38521(11) 0.45928(4) 1.01601(3) 0.03951(15) Uani 1 1 d . . . . .
H5 H 0.4017 0.5026 1.0485 0.047 Uiso 1 1 calc R U . . .
C6 C 0.55351(11) 0.45448(4) 0.96435(3) 0.03795(15) Uani 1 1 d . . . . .
H6 H 0.6868 0.4949 0.9616 0.046 Uiso 1 1 calc R U . . .
C7 C 0.31768(11) 0.26353(4) 0.86966(3) 0.03657(14) Uani 1 1 d . . . . .
C8 C 0.48623(10) 0.26167(4) 0.81521(3) 0.03391(14) Uani 1 1 d . . . . .
C9 C 0.46436(11) 0.19833(3) 0.76581(3) 0.03404(14) Uani 1 1 d . . . . .
C10 C 0.26952(12) 0.13817(4) 0.77158(3) 0.04090(16) Uani 1 1 d . . . . .
H10 H 0.2487 0.0959 0.7385 0.049 Uiso 1 1 calc R U . . .
C11 C 0.10696(12) 0.14006(4) 0.82540(3) 0.04298(16) Uani 1 1 d . . . . .
H11 H -0.0231 0.0985 0.8288 0.052 Uiso 1 1 calc R U . . .
C12 C 0.13082(12) 0.20088(4) 0.87379(3) 0.04099(16) Uani 1 1 d . . . . .
H12 H 0.0189 0.2003 0.9105 0.049 Uiso 1 1 calc R U . . .
C13 C 0.64293(11) 0.19654(3) 0.70964(3) 0.03351(14) Uani 1 1 d . . . . .
C14 C 0.83289(10) 0.25990(3) 0.70243(3) 0.03076(13) Uani 1 1 d . . . . .
C15 C 1.00026(11) 0.25695(3) 0.64736(3) 0.03335(14) Uani 1 1 d . . . . .
C16 C 0.97551(12) 0.19032(4) 0.60231(3) 0.04125(16) Uani 1 1 d . . . . .
H16 H 1.0878 0.1874 0.5658 0.050 Uiso 1 1 calc R U . . .
C17 C 0.79241(13) 0.12865(4) 0.60946(3) 0.04606(18) Uani 1 1 d . . . . .
H17 H 0.7793 0.0839 0.5781 0.055 Uiso 1 1 calc R U . . .
C18 C 0.62830(12) 0.13193(4) 0.66224(3) 0.04095(16) Uani 1 1 d . . . . .
H18 H 0.5020 0.0892 0.6665 0.049 Uiso 1 1 calc R U . . .
C19 C 1.19652(11) 0.32243(4) 0.63790(3) 0.03147(14) Uani 1 1 d . . . . .
C20 C 1.22109(11) 0.38841(3) 0.68413(3) 0.03007(13) Uani 1 1 d . . . . .
C21 C 1.41027(10) 0.44976(3) 0.67584(3) 0.03142(14) Uani 1 1 d . . . . .
H21 H 1.4244 0.4948 0.7070 0.038 Uiso 1 1 calc R U . . .
C22 C 1.57648(11) 0.44638(4) 0.62356(3) 0.03506(15) Uani 1 1 d . . . . .
H22 H 1.7054 0.4881 0.6190 0.042 Uiso 1 1 calc R U . . .
C23 C 1.55339(12) 0.38125(4) 0.57761(3) 0.03654(15) Uani 1 1 d . . . . .
H23 H 1.6675 0.3783 0.5414 0.044 Uiso 1 1 calc R U . . .
C24 C 1.36588(12) 0.32076(4) 0.58406(3) 0.03651(15) Uani 1 1 d . . . . .
H24 H 1.3505 0.2772 0.5517 0.044 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A N1 1.5393(13) . ?
O1A H1AA 0.86(2) . ?
O1A H1A 0.730(8) . ?
O1B B1 1.4146(8) . ?
O1B H2AA 0.824(11) . ?
O1B H1B 0.595(12) . ?
N1 B2 1.4049(7) . ?
N1 C1 1.4362(8) . ?
N1 H1A 0.852(8) . ?
N2 B1 1.4374(7) . ?
N2 C14 1.4536(7) . ?
N2 B2 1.4628(7) . ?
B1 C20 1.4818(8) . ?
B2 C8 1.4999(8) . ?
C1 C6 1.4021(8) . ?
C1 C2 1.4127(8) . ?
C2 C3 1.4092(8) . ?
C2 C7 1.4625(8) . ?
C3 C4 1.3699(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.3913(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.3757(8) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.3966(9) . ?
C7 C8 1.4181(8) . ?
C8 C9 1.4148(8) . ?
C9 C10 1.4025(8) . ?
C9 C13 1.4785(8) . ?
C10 C11 1.3884(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.3735(9) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.3981(8) . ?
C13 C14 1.4211(8) . ?
C14 C15 1.4243(8) . ?
C15 C16 1.3937(8) . ?
C15 C19 1.4731(8) . ?
C16 C17 1.3768(9) . ?
C16 H16 0.9500 . ?
C17 C18 1.3776(9) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.4018(7) . ?
C19 C24 1.4112(8) . ?
C20 C21 1.3986(8) . ?
C21 C22 1.3771(8) . ?
C21 H21 0.9500 . ?
C22 C23 1.3875(8) . ?
C22 H22 0.9500 . ?
C23 C24 1.3790(9) . ?
C23 H23 0.9500 . ?
C24 H24 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
N1 O1A H1AA 114.3(14) . . ?
H1AA O1A H1A 102.9(15) . . ?
H2AA O1B H1B 87.4(15) . . ?
B2 N1 C1 124.46(5) . . ?
B2 N1 O1A 113.69(6) . . ?
C1 N1 O1A 121.32(6) . . ?
B2 N1 H1A 121.5(5) . . ?
C1 N1 H1A 114.0(5) . . ?
B1 N2 C14 117.80(4) . . ?
B1 N2 B2 122.00(4) . . ?
C14 N2 B2 120.20(4) . . ?
O1B B1 C20 123.13(5) . . ?
N2 B1 C20 122.04(5) . . ?
N1 B2 N2 124.38(5) . . ?
N1 B2 C8 116.32(5) . . ?
N2 B2 C8 119.30(5) . . ?
C6 C1 C2 119.66(5) . . ?
C6 C1 N1 121.49(5) . . ?
C2 C1 N1 118.83(5) . . ?
C3 C2 C1 117.25(5) . . ?
C3 C2 C7 123.04(5) . . ?
C1 C2 C7 119.71(5) . . ?
C4 C3 C2 122.15(6) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 120.23(6) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.18(6) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 121.50(6) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C12 C7 C8 118.48(5) . . ?
C12 C7 C2 120.80(5) . . ?
C8 C7 C2 120.71(5) . . ?
C9 C8 C7 120.84(5) . . ?
C9 C8 B2 119.24(5) . . ?
C7 C8 B2 119.91(5) . . ?
C10 C9 C8 118.30(5) . . ?
C10 C9 C13 121.38(5) . . ?
C8 C9 C13 120.32(5) . . ?
C11 C10 C9 120.40(6) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 121.18(6) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C7 120.77(6) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C18 C13 C14 118.42(5) . . ?
C18 C13 C9 120.42(5) . . ?
C14 C13 C9 121.16(5) . . ?
C13 C14 C15 119.81(5) . . ?
C13 C14 N2 119.73(5) . . ?
C15 C14 N2 120.46(5) . . ?
C16 C15 C14 118.57(5) . . ?
C16 C15 C19 120.29(5) . . ?
C14 C15 C19 121.14(5) . . ?
C17 C16 C15 121.64(6) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 119.90(6) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C13 121.65(6) . . ?
C17 C18 H18 119.2 . . ?
C13 C18 H18 119.2 . . ?
C20 C19 C24 118.07(5) . . ?
C20 C19 C15 119.59(5) . . ?
C24 C19 C15 122.33(5) . . ?
C21 C20 C19 119.65(5) . . ?
C21 C20 B1 121.39(5) . . ?
C19 C20 B1 118.95(5) . . ?
C22 C21 C20 121.50(5) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C21 C22 C23 119.18(5) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C24 C23 C22 120.45(5) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C19 121.13(5) . . ?
C23 C24 H24 119.4 . . ?
C19 C24 H24 119.4 . . ?

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.031

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 987402'
