# 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_nl043d
_database_code_depnum_ccdc_archive 'CCDC 1423210'

_audit_update_record             
;
2015-09-09 deposited with the CCDC.
2015-10-22 downloaded from the CCDC.
;
_publcif_datablock.id            {670030e0-2226-4039-9562-cee8236b5de5}
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Adduct of N-methylimidazole and 4-(benzo[d][1,3,2]dioxaborol-2-yl)benzonitrile'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 B N3 O2'
_chemical_formula_sum            'C17 H14 B N3 O2'
_chemical_formula_weight         303.12

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           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'

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

_cell_length_a                   19.7880(17)
_cell_length_b                   6.0950(6)
_cell_length_c                   12.5928(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1518.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    160
_cell_measurement_theta_min      3
_cell_measurement_theta_max      22

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6349
_exptl_absorpt_correction_T_max  0.7460
_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            23705
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.24
_diffrn_reflns_theta_max         30.03
_reflns_number_total             4341
_reflns_number_gt                4062
_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)+(0.0444P)²+0.2912P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(7)
_refine_ls_number_reflns         4341
_refine_ls_number_parameters     209
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0861
_refine_ls_wR_factor_gt          0.0824
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_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 0.53938(4) 0.41639(14) 0.73126(7) 0.01827(18) Uani 1 1 d . . .
O2 O 0.52807(4) 0.75590(14) 0.63859(7) 0.01774(18) Uani 1 1 d . . .
N1 N 0.45688(5) 0.42830(16) 0.58514(8) 0.01604(19) Uani 1 1 d . . .
N2 N 0.44410(5) 0.17214(17) 0.46380(8) 0.0177(2) Uani 1 1 d . . .
N3 N 0.20895(6) 0.8848(2) 0.98865(10) 0.0253(2) Uani 1 1 d . . .
B1 B 0.48868(6) 0.5656(2) 0.68201(11) 0.0161(2) Uani 1 1 d . . .
C1 C 0.39778(6) 0.4723(2) 0.52891(11) 0.0198(2) Uani 1 1 d . . .
H1 H 0.3681 0.5923 0.5411 0.024 Uiso 1 1 calc R . .
C2 C 0.38971(6) 0.3146(2) 0.45381(11) 0.0206(2) Uani 1 1 d . . .
H2 H 0.3538 0.3038 0.4040 0.025 Uiso 1 1 calc R . .
C3 C 0.48325(6) 0.2451(2) 0.54361(10) 0.0175(2) Uani 1 1 d . . .
H3 H 0.5237 0.1767 0.5671 0.021 Uiso 1 1 calc R . .
C4 C 0.45604(7) -0.0244(2) 0.39919(11) 0.0233(3) Uani 1 1 d . . .
H4A H 0.4680 0.0193 0.3267 0.035 Uiso 1 1 calc R . .
H4B H 0.4150 -0.1141 0.3976 0.035 Uiso 1 1 calc R . .
H4C H 0.4931 -0.1097 0.4301 0.035 Uiso 1 1 calc R . .
C5 C 0.60153(6) 0.4978(2) 0.70272(9) 0.0161(2) Uani 1 1 d . . .
C6 C 0.66412(6) 0.4049(2) 0.72121(10) 0.0190(2) Uani 1 1 d . . .
H6 H 0.6683 0.2660 0.7548 0.023 Uiso 1 1 calc R . .
C7 C 0.72165(6) 0.5242(2) 0.68832(11) 0.0223(3) Uani 1 1 d . . .
H7 H 0.7654 0.4641 0.6994 0.027 Uiso 1 1 calc R . .
C8 C 0.71511(6) 0.7290(2) 0.63980(11) 0.0223(3) Uani 1 1 d . . .
H8 H 0.7545 0.8080 0.6200 0.027 Uiso 1 1 calc R . .
C9 C 0.65089(6) 0.8207(2) 0.61966(10) 0.0190(2) Uani 1 1 d . . .
H9 H 0.6463 0.9597 0.5863 0.023 Uiso 1 1 calc R . .
C10 C 0.59483(6) 0.7005(2) 0.65034(10) 0.0157(2) Uani 1 1 d . . .
C11 C 0.42806(6) 0.6454(2) 0.75840(10) 0.0166(2) Uani 1 1 d . . .
C12 C 0.39515(6) 0.8472(2) 0.74038(11) 0.0224(3) Uani 1 1 d . . .
H12 H 0.4108 0.9399 0.6850 0.027 Uiso 1 1 calc R . .
C13 C 0.34021(6) 0.9145(2) 0.80170(11) 0.0228(3) Uani 1 1 d . . .
H13 H 0.3185 1.0507 0.7879 0.027 Uiso 1 1 calc R . .
C14 C 0.31740(6) 0.7780(2) 0.88419(10) 0.0182(2) Uani 1 1 d . . .
C15 C 0.34992(7) 0.5792(2) 0.90591(11) 0.0227(3) Uani 1 1 d . . .
H15 H 0.3349 0.4886 0.9626 0.027 Uiso 1 1 calc R . .
C16 C 0.40474(6) 0.5154(2) 0.84307(11) 0.0215(3) Uani 1 1 d . . .
H16 H 0.4269 0.3806 0.8580 0.026 Uiso 1 1 calc R . .
C17 C 0.25737(6) 0.8385(2) 0.94347(10) 0.0208(2) 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 C5 1.3742(14) . ?
O1 B1 1.4894(16) . ?
O2 C10 1.3715(13) . ?
O2 B1 1.5004(16) . ?
N1 C3 1.3388(16) . ?
N1 C1 1.3932(15) . ?
N1 B1 1.6078(17) . ?
N2 C3 1.3447(16) . ?
N2 C2 1.3886(16) . ?
N2 C4 1.4673(16) . ?
N3 C17 1.1495(18) . ?
B1 C11 1.6126(17) . ?
C1 C2 1.3579(19) . ?
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 1.3817(16) . ?
C5 C10 1.4066(17) . ?
C6 C7 1.4127(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.396(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.4111(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.3842(16) . ?
C9 H9 0.9500 . ?
C11 C16 1.4060(18) . ?
C11 C12 1.4105(17) . ?
C12 C13 1.3951(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.4056(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.3991(18) . ?
C14 C17 1.4505(17) . ?
C15 C16 1.3979(18) . ?
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 105.86(9) . . ?
C10 O2 B1 105.71(9) . . ?
C3 N1 C1 106.81(11) . . ?
C3 N1 B1 125.31(10) . . ?
C1 N1 B1 127.88(10) . . ?
C3 N2 C2 107.90(10) . . ?
C3 N2 C4 126.28(11) . . ?
C2 N2 C4 125.82(11) . . ?
O1 B1 O2 105.90(9) . . ?
O1 B1 N1 105.16(9) . . ?
O2 B1 N1 109.22(10) . . ?
O1 B1 C11 115.89(10) . . ?
O2 B1 C11 111.77(10) . . ?
N1 B1 C11 108.56(9) . . ?
C2 C1 N1 108.45(11) . . ?
C2 C1 H1 125.8 . . ?
N1 C1 H1 125.8 . . ?
C1 C2 N2 106.76(11) . . ?
C1 C2 H2 126.6 . . ?
N2 C2 H2 126.6 . . ?
N1 C3 N2 110.08(11) . . ?
N1 C3 H3 125.0 . . ?
N2 C3 H3 125.0 . . ?
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 . . ?
O1 C5 C6 127.59(11) . . ?
O1 C5 C10 110.83(10) . . ?
C6 C5 C10 121.58(11) . . ?
C5 C6 C7 117.51(11) . . ?
C5 C6 H6 121.2 . . ?
C7 C6 H6 121.2 . . ?
C8 C7 C6 120.92(11) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 121.07(11) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 117.52(11) . . ?
C10 C9 H9 121.2 . . ?
C8 C9 H9 121.2 . . ?
O2 C10 C9 127.70(11) . . ?
O2 C10 C5 110.95(10) . . ?
C9 C10 C5 121.33(11) . . ?
C16 C11 C12 117.50(11) . . ?
C16 C11 B1 121.79(11) . . ?
C12 C11 B1 120.69(11) . . ?
C13 C12 C11 121.82(12) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C14 119.03(12) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 120.64(11) . . ?
C15 C14 C17 119.76(12) . . ?
C13 C14 C17 119.52(11) . . ?
C16 C15 C14 119.14(12) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C11 121.84(12) . . ?
C15 C16 H16 119.1 . . ?
C11 C16 H16 119.1 . . ?
N3 C17 C14 178.49(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
C5 O1 B1 O2 -8.78(12) . . . . ?
C5 O1 B1 N1 106.81(10) . . . . ?
C5 O1 B1 C11 -133.32(10) . . . . ?
C10 O2 B1 O1 7.38(12) . . . . ?
C10 O2 B1 N1 -105.41(10) . . . . ?
C10 O2 B1 C11 134.44(10) . . . . ?
C3 N1 B1 O1 -15.11(15) . . . . ?
C1 N1 B1 O1 164.45(11) . . . . ?
C3 N1 B1 O2 98.17(13) . . . . ?
C1 N1 B1 O2 -82.28(14) . . . . ?
C3 N1 B1 C11 -139.73(11) . . . . ?
C1 N1 B1 C11 39.82(16) . . . . ?
C3 N1 C1 C2 -0.27(14) . . . . ?
B1 N1 C1 C2 -179.89(11) . . . . ?
N1 C1 C2 N2 0.08(14) . . . . ?
C3 N2 C2 C1 0.14(14) . . . . ?
C4 N2 C2 C1 179.51(12) . . . . ?
C1 N1 C3 N2 0.36(14) . . . . ?
B1 N1 C3 N2 179.99(10) . . . . ?
C2 N2 C3 N1 -0.31(14) . . . . ?
C4 N2 C3 N1 -179.69(11) . . . . ?
B1 O1 C5 C6 -173.71(12) . . . . ?
B1 O1 C5 C10 7.08(13) . . . . ?
O1 C5 C6 C7 -177.30(12) . . . . ?
C10 C5 C6 C7 1.84(18) . . . . ?
C5 C6 C7 C8 0.53(19) . . . . ?
C6 C7 C8 C9 -1.6(2) . . . . ?
C7 C8 C9 C10 0.36(19) . . . . ?
B1 O2 C10 C9 178.27(12) . . . . ?
B1 O2 C10 C5 -3.32(12) . . . . ?
C8 C9 C10 O2 -179.74(12) . . . . ?
C8 C9 C10 C5 2.00(18) . . . . ?
O1 C5 C10 O2 -2.45(13) . . . . ?
C6 C5 C10 O2 178.28(11) . . . . ?
O1 C5 C10 C9 176.08(11) . . . . ?
C6 C5 C10 C9 -3.19(18) . . . . ?
O1 B1 C11 C16 -29.01(16) . . . . ?
O2 B1 C11 C16 -150.46(12) . . . . ?
N1 B1 C11 C16 89.01(13) . . . . ?
O1 B1 C11 C12 152.76(11) . . . . ?
O2 B1 C11 C12 31.31(15) . . . . ?
N1 B1 C11 C12 -89.22(13) . . . . ?
C16 C11 C12 C13 -1.82(19) . . . . ?
B1 C11 C12 C13 176.48(12) . . . . ?
C11 C12 C13 C14 0.5(2) . . . . ?
C12 C13 C14 C15 1.1(2) . . . . ?
C12 C13 C14 C17 -175.55(12) . . . . ?
C13 C14 C15 C16 -1.27(19) . . . . ?
C17 C14 C15 C16 175.39(12) . . . . ?
C14 C15 C16 C11 -0.2(2) . . . . ?
C12 C11 C16 C15 1.66(19) . . . . ?
B1 C11 C16 C15 -176.62(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        30.03
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.040


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?

_exptl_crystal_recrystallization_method 'Vapour Deposition'
