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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_nl349a
_database_code_depnum_ccdc_archive 'CCDC 1423213'

_audit_update_record             
;
2015-09-09 deposited with the CCDC.
2015-10-22 downloaded from the CCDC.
;
_publcif_datablock.id            {882c22b0-08f3-4d27-8c3b-91e6d19ff52d}
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Adduct of N-methylimidazole and 2-phenylbenzo[d][1,3,2]dioxaborole'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 B N2 O2'
_chemical_formula_sum            'C16 H15 B N2 O2'
_chemical_formula_weight         278.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   8.0935(3)
_cell_length_b                   8.3643(5)
_cell_length_c                   20.7488(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.350(6)
_cell_angle_gamma                90.00
_cell_volume                     1400.57(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    253
_cell_measurement_theta_min      3
_cell_measurement_theta_max      22

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6242
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS 2008, Bruker AXS, 2008'

_exptl_special_details           ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3193
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         27.54
_reflns_number_total             3193
_reflns_number_gt                2964
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs, 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+11.4981P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.046(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3193
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1295
_refine_ls_R_factor_gt           0.1247
_refine_ls_wR_factor_ref         0.3266
_refine_ls_wR_factor_gt          0.3250
_refine_ls_goodness_of_fit_ref   1.285
_refine_ls_restrained_S_all      1.285
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5796(5) 0.0726(5) 0.09995(18) 0.0168(9) Uani 1 1 d . . .
O2 O 0.4331(5) 0.2387(5) 0.16833(19) 0.0195(10) Uani 1 1 d . . .
N1 N 0.3732(6) 0.2589(6) 0.0488(2) 0.0175(10) Uani 1 1 d . . .
N2 N 0.3698(6) 0.3426(6) -0.0512(2) 0.0203(11) Uani 1 1 d . . .
B1 B 0.4111(8) 0.1379(8) 0.1099(3) 0.0162(13) Uani 1 1 d . . .
C1 C 0.2816(7) 0.3975(7) 0.0438(3) 0.0203(12) Uani 1 1 d . . .
H1 H 0.2281 0.4464 0.0780 0.024 Uiso 1 1 calc R . .
C2 C 0.2798(8) 0.4531(7) -0.0176(3) 0.0227(13) Uani 1 1 d . . .
H2 H 0.2279 0.5478 -0.0343 0.027 Uiso 1 1 calc R . .
C3 C 0.4242(8) 0.2291(7) -0.0098(3) 0.0200(12) Uani 1 1 d . . .
H3 H 0.4896 0.1400 -0.0204 0.024 Uiso 1 1 calc R . .
C4 C 0.4008(9) 0.3453(8) -0.1200(3) 0.0284(15) Uani 1 1 d . . .
H4A H 0.4575 0.4449 -0.1299 0.043 Uiso 1 1 calc R . .
H4B H 0.2952 0.3389 -0.1463 0.043 Uiso 1 1 calc R . .
H4C H 0.4705 0.2540 -0.1298 0.043 Uiso 1 1 calc R . .
C5 C 0.6885(7) 0.1646(7) 0.1385(3) 0.0145(11) Uani 1 1 d . . .
C6 C 0.8584(7) 0.1634(8) 0.1408(3) 0.0213(13) Uani 1 1 d . . .
H6 H 0.9157 0.0957 0.1132 0.026 Uiso 1 1 calc R . .
C7 C 0.9456(8) 0.2671(8) 0.1857(3) 0.0234(13) Uani 1 1 d . . .
H7 H 1.0631 0.2721 0.1876 0.028 Uiso 1 1 calc R . .
C8 C 0.8580(8) 0.3621(8) 0.2274(3) 0.0238(13) Uani 1 1 d . . .
H8 H 0.9171 0.4298 0.2578 0.029 Uiso 1 1 calc R . .
C9 C 0.6843(8) 0.3581(7) 0.2246(3) 0.0210(13) Uani 1 1 d . . .
H9 H 0.6253 0.4216 0.2531 0.025 Uiso 1 1 calc R . .
C10 C 0.6020(7) 0.2609(7) 0.1800(3) 0.0162(11) Uani 1 1 d . . .
C11 C 0.2728(7) 0.0027(7) 0.1108(3) 0.0160(11) Uani 1 1 d . . .
C12 C 0.2440(7) -0.0741(8) 0.1699(3) 0.0206(12) Uani 1 1 d . . .
H12 H 0.2962 -0.0330 0.2090 0.025 Uiso 1 1 calc R . .
C13 C 0.1422(7) -0.2069(8) 0.1725(3) 0.0219(13) Uani 1 1 d . . .
H13 H 0.1255 -0.2555 0.2129 0.026 Uiso 1 1 calc R . .
C14 C 0.0648(8) -0.2687(8) 0.1160(3) 0.0239(13) Uani 1 1 d . . .
H14 H -0.0029 -0.3612 0.1173 0.029 Uiso 1 1 calc R . .
C15 C 0.0873(7) -0.1936(7) 0.0566(3) 0.0224(13) Uani 1 1 d . . .
H15 H 0.0315 -0.2328 0.0179 0.027 Uiso 1 1 calc R . .
C16 C 0.1908(7) -0.0625(7) 0.0549(3) 0.0186(12) Uani 1 1 d . . .
H16 H 0.2070 -0.0147 0.0143 0.022 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.379(6) . ?
O1 B1 1.498(7) . ?
O2 C10 1.383(7) . ?
O2 B1 1.476(7) . ?
N1 C3 1.337(7) . ?
N1 C1 1.376(7) . ?
N1 B1 1.633(8) . ?
N2 C3 1.332(8) . ?
N2 C2 1.395(8) . ?
N2 C4 1.469(8) . ?
B1 C11 1.592(8) . ?
C1 C2 1.356(9) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.372(8) . ?
C5 C10 1.405(8) . ?
C6 C7 1.421(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.405(9) . ?
C7 H7 0.9500 . ?
C8 C9 1.403(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.366(8) . ?
C9 H9 0.9500 . ?
C11 C16 1.403(8) . ?
C11 C12 1.418(8) . ?
C12 C13 1.387(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.406(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(9) . ?
C15 H15 0.9500 . ?
C16 H16 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
C5 O1 B1 105.3(4) . . ?
C10 O2 B1 106.1(4) . . ?
C3 N1 C1 106.9(5) . . ?
C3 N1 B1 122.6(5) . . ?
C1 N1 B1 130.5(5) . . ?
C3 N2 C2 108.0(5) . . ?
C3 N2 C4 124.4(5) . . ?
C2 N2 C4 127.6(5) . . ?
O2 B1 O1 105.5(4) . . ?
O2 B1 C11 115.9(5) . . ?
O1 B1 C11 113.0(5) . . ?
O2 B1 N1 106.7(5) . . ?
O1 B1 N1 103.8(4) . . ?
C11 B1 N1 111.0(4) . . ?
C2 C1 N1 109.1(5) . . ?
C2 C1 H1 125.5 . . ?
N1 C1 H1 125.5 . . ?
C1 C2 N2 105.9(5) . . ?
C1 C2 H2 127.0 . . ?
N2 C2 H2 127.0 . . ?
N2 C3 N1 110.1(5) . . ?
N2 C3 H3 124.9 . . ?
N1 C3 H3 124.9 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 O1 127.6(5) . . ?
C6 C5 C10 121.9(5) . . ?
O1 C5 C10 110.4(5) . . ?
C5 C6 C7 117.7(6) . . ?
C5 C6 H6 121.2 . . ?
C7 C6 H6 121.2 . . ?
C8 C7 C6 120.0(6) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 120.8(6) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 118.5(6) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C9 C10 O2 128.6(5) . . ?
C9 C10 C5 121.1(5) . . ?
O2 C10 C5 110.4(5) . . ?
C16 C11 C12 116.1(5) . . ?
C16 C11 B1 123.7(5) . . ?
C12 C11 B1 119.6(5) . . ?
C13 C12 C11 122.3(6) . . ?
C13 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C14 C13 C12 119.7(6) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 119.6(6) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 119.8(6) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C11 122.4(5) . . ?
C15 C16 H16 118.8 . . ?
C11 C16 H16 118.8 . . ?

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
C10 O2 B1 O1 13.8(6) . . . . ?
C10 O2 B1 C11 139.6(5) . . . . ?
C10 O2 B1 N1 -96.2(5) . . . . ?
C5 O1 B1 O2 -15.0(6) . . . . ?
C5 O1 B1 C11 -142.6(5) . . . . ?
C5 O1 B1 N1 97.1(5) . . . . ?
C3 N1 B1 O2 146.4(5) . . . . ?
C1 N1 B1 O2 -37.9(8) . . . . ?
C3 N1 B1 O1 35.2(7) . . . . ?
C1 N1 B1 O1 -149.0(5) . . . . ?
C3 N1 B1 C11 -86.4(6) . . . . ?
C1 N1 B1 C11 89.3(7) . . . . ?
C3 N1 C1 C2 -1.1(7) . . . . ?
B1 N1 C1 C2 -177.4(5) . . . . ?
N1 C1 C2 N2 1.4(7) . . . . ?
C3 N2 C2 C1 -1.2(7) . . . . ?
C4 N2 C2 C1 178.2(6) . . . . ?
C2 N2 C3 N1 0.6(7) . . . . ?
C4 N2 C3 N1 -178.9(5) . . . . ?
C1 N1 C3 N2 0.3(7) . . . . ?
B1 N1 C3 N2 176.9(5) . . . . ?
B1 O1 C5 C6 -172.1(6) . . . . ?
B1 O1 C5 C10 10.7(6) . . . . ?
O1 C5 C6 C7 -178.6(5) . . . . ?
C10 C5 C6 C7 -1.7(9) . . . . ?
C5 C6 C7 C8 2.1(9) . . . . ?
C6 C7 C8 C9 -1.0(10) . . . . ?
C7 C8 C9 C10 -0.6(10) . . . . ?
C8 C9 C10 O2 -179.5(6) . . . . ?
C8 C9 C10 C5 1.1(9) . . . . ?
B1 O2 C10 C9 172.8(6) . . . . ?
B1 O2 C10 C5 -7.7(6) . . . . ?
C6 C5 C10 C9 0.2(9) . . . . ?
O1 C5 C10 C9 177.5(5) . . . . ?
C6 C5 C10 O2 -179.4(5) . . . . ?
O1 C5 C10 O2 -2.1(6) . . . . ?
O2 B1 C11 C16 155.1(5) . . . . ?
O1 B1 C11 C16 -82.9(7) . . . . ?
N1 B1 C11 C16 33.2(7) . . . . ?
O2 B1 C11 C12 -33.9(8) . . . . ?
O1 B1 C11 C12 88.0(6) . . . . ?
N1 B1 C11 C12 -155.9(5) . . . . ?
C16 C11 C12 C13 0.7(8) . . . . ?
B1 C11 C12 C13 -171.0(5) . . . . ?
C11 C12 C13 C14 0.0(9) . . . . ?
C12 C13 C14 C15 -1.5(9) . . . . ?
C13 C14 C15 C16 2.3(9) . . . . ?
C14 C15 C16 C11 -1.6(9) . . . . ?
C12 C11 C16 C15 0.2(8) . . . . ?
B1 C11 C16 C15 171.4(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.145


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
