# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

 
data_compound1
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C30 H44 Al B Br2 N2 O' 
_chemical_formula_weight          646.28 
 
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' 
 'Al'  'Al'   0.0645   0.0514 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Br'  'Br'  -0.2901   2.4595 
 '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    P2(1)/c
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
 
_cell_length_a                    14.1479(7) 
_cell_length_b                    12.1971(7) 
_cell_length_c                    19.3891(13) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  100.086(6) 
_cell_angle_gamma                 90.00 
_cell_volume                      3294.1(3) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     123(2) 
_cell_measurement_reflns_used     6455 
_cell_measurement_theta_min       2.92 
_cell_measurement_theta_max       26.00
 
_exptl_crystal_description        'block' 
_exptl_crystal_colour             'colourless' 
_exptl_crystal_size_max           0.15 
_exptl_crystal_size_mid           0.10 
_exptl_crystal_size_min           0.10 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.303 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1336 
_exptl_absorpt_coefficient_mu     2.511 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.701 
_exptl_absorpt_correction_T_max   0.787 
_exptl_absorpt_process_details    'Sortav (Blessing)' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       123(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 X8' 
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             15151 
_diffrn_reflns_av_R_equivalents   0.0387 
_diffrn_reflns_av_sigmaI/netI     0.0575 
_diffrn_reflns_limit_h_min        -17 
_diffrn_reflns_limit_h_max        14 
_diffrn_reflns_limit_k_min        -10 
_diffrn_reflns_limit_k_max        15 
_diffrn_reflns_limit_l_min        -16 
_diffrn_reflns_limit_l_max        23 
_diffrn_reflns_theta_min          2.92 
_diffrn_reflns_theta_max          26.00 
_reflns_number_total              6455 
_reflns_number_gt                 4717 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0314P)²+1.1598P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          6455 
_refine_ls_number_parameters      350 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0686 
_refine_ls_R_factor_gt            0.0379 
_refine_ls_wR_factor_ref          0.0831 
_refine_ls_wR_factor_gt           0.0739 
_refine_ls_goodness_of_fit_ref    1.019 
_refine_ls_restrained_S_all       1.019 
_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 
Br1 Br 0.54425(2) 0.85974(2) 0.139631(19) 0.04193(11) Uani 1 1 d . . . 
Al1 Al 0.62094(5) 1.01186(7) 0.19551(4) 0.02397(19) Uani 1 1 d . . . 
O1 O 0.53873(12) 1.12372(15) 0.15401(10) 0.0271(4) Uani 1 1 d . . . 
N1 N 0.81322(14) 1.13022(17) 0.16337(11) 0.0211(5) Uani 1 1 d . . . 
C27 C 0.5266(2) 1.1476(3) 0.07829(15) 0.0370(8) Uani 1 1 d . . . 
H27A H 0.5001 1.0835 0.0501 0.044 Uiso 1 1 calc R . . 
H27B H 0.5884 1.1687 0.0648 0.044 Uiso 1 1 calc R . . 
Br2 Br 0.59521(2) 1.02198(3) 0.310096(17) 0.04489(11) Uani 1 1 d . . . 
N2 N 0.84533(15) 0.96760(17) 0.21778(11) 0.0219(5) Uani 1 1 d . . . 
C11 C 0.8365(2) 1.3462(3) 0.26549(17) 0.0390(8) Uani 1 1 d . . . 
H11A H 0.8835 1.2929 0.2544 0.058 Uiso 1 1 calc R . . 
H11B H 0.8389 1.3485 0.3163 0.058 Uiso 1 1 calc R . . 
H11C H 0.8516 1.4189 0.2489 0.058 Uiso 1 1 calc R . . 
C4 C 0.7707(2) 1.2127(3) 0.04774(15) 0.0342(7) Uani 1 1 d . . . 
C12 C 0.8131(2) 1.1146(3) 0.01524(17) 0.0484(9) Uani 1 1 d . . . 
H12 H 0.8409 1.0643 0.0543 0.058 Uiso 1 1 calc R . . 
C13 C 0.8949(3) 1.1496(4) -0.0222(2) 0.0888(17) Uani 1 1 d . . . 
H13A H 0.8703 1.2013 -0.0598 0.133 Uiso 1 1 calc R . . 
H13B H 0.9210 1.0849 -0.0422 0.133 Uiso 1 1 calc R . . 
H13C H 0.9456 1.1849 0.0113 0.133 Uiso 1 1 calc R . . 
C14 C 0.7365(3) 1.0514(4) -0.0332(2) 0.0851(16) Uani 1 1 d . . . 
H14A H 0.6872 1.0265 -0.0070 0.128 Uiso 1 1 calc R . . 
H14B H 0.7656 0.9877 -0.0521 0.128 Uiso 1 1 calc R . . 
H14C H 0.7070 1.0989 -0.0718 0.128 Uiso 1 1 calc R . . 
C6 C 0.6863(3) 1.3844(3) 0.0350(2) 0.0560(10) Uani 1 1 d . . . 
H6 H 0.6570 1.4419 0.0057 0.067 Uiso 1 1 calc R . . 
C5 C 0.7268(3) 1.2979(3) 0.00624(18) 0.0518(10) Uani 1 1 d . . . 
H5 H 0.7249 1.2958 -0.0430 0.062 Uiso 1 1 calc R . . 
C29 C 0.3914(2) 1.2179(3) 0.1187(2) 0.0556(10) Uani 1 1 d . . . 
H29A H 0.3397 1.1673 0.0974 0.067 Uiso 1 1 calc R . . 
H29B H 0.3619 1.2860 0.1328 0.067 Uiso 1 1 calc R . . 
C15 C 0.84347(17) 0.8617(2) 0.24998(14) 0.0216(6) Uani 1 1 d . . . 
C30 C 0.4531(2) 1.1655(2) 0.18059(18) 0.0398(8) Uani 1 1 d . . . 
H30A H 0.4722 1.2198 0.2184 0.048 Uiso 1 1 calc R . . 
H30B H 0.4185 1.1046 0.1990 0.048 Uiso 1 1 calc R . . 
C26 C 0.9032(2) 0.7873(3) 0.10300(17) 0.0431(8) Uani 1 1 d . . . 
H26A H 0.9383 0.8506 0.1257 0.065 Uiso 1 1 calc R . . 
H26B H 0.8927 0.7969 0.0520 0.065 Uiso 1 1 calc R . . 
H26C H 0.9408 0.7205 0.1157 0.065 Uiso 1 1 calc R . . 
C10 C 0.6611(2) 1.3890(3) 0.25172(19) 0.0511(10) Uani 1 1 d . . . 
H10A H 0.6765 1.4650 0.2416 0.077 Uiso 1 1 calc R . . 
H10B H 0.6618 1.3808 0.3021 0.077 Uiso 1 1 calc R . . 
H10C H 0.5972 1.3706 0.2259 0.077 Uiso 1 1 calc R . . 
C23 C 1.0021(2) 0.9525(3) 0.39527(18) 0.0481(9) Uani 1 1 d . . . 
H23A H 1.0205 0.8872 0.4239 0.072 Uiso 1 1 calc R . . 
H23B H 1.0202 1.0184 0.4234 0.072 Uiso 1 1 calc R . . 
H23C H 1.0352 0.9522 0.3549 0.072 Uiso 1 1 calc R . . 
C9 C 0.7355(2) 1.3122(2) 0.22926(15) 0.0298(7) Uani 1 1 d . . . 
H9 H 0.7230 1.2368 0.2457 0.036 Uiso 1 1 calc R . . 
C20 C 0.86364(18) 0.8531(2) 0.32347(14) 0.0250(6) Uani 1 1 d . . . 
C19 C 0.85902(19) 0.7495(2) 0.35297(15) 0.0282(6) Uani 1 1 d . . . 
H19 H 0.8727 0.7416 0.4025 0.034 Uiso 1 1 calc R . . 
B1 B 0.7666(2) 1.0373(2) 0.18847(16) 0.0212(7) Uani 1 1 d . . . 
C16 C 0.82100(18) 0.7689(2) 0.20715(14) 0.0243(6) Uani 1 1 d . . . 
C25 C 0.7483(2) 0.6836(2) 0.08901(16) 0.0361(7) Uani 1 1 d . . . 
H25A H 0.7853 0.6155 0.0973 0.054 Uiso 1 1 calc R . . 
H25B H 0.7350 0.6993 0.0387 0.054 Uiso 1 1 calc R . . 
H25C H 0.6877 0.6755 0.1063 0.054 Uiso 1 1 calc R . . 
C24 C 0.8059(2) 0.7775(2) 0.12745(15) 0.0289(7) Uani 1 1 d . . . 
H24 H 0.7696 0.8468 0.1138 0.035 Uiso 1 1 calc R . . 
C18 C 0.8349(2) 0.6582(2) 0.31158(16) 0.0306(7) Uani 1 1 d . . . 
H18 H 0.8308 0.5885 0.3328 0.037 Uiso 1 1 calc R . . 
C8 C 0.73059(18) 1.3072(2) 0.15075(15) 0.0253(6) Uani 1 1 d . . . 
C21 C 0.8930(2) 0.9522(2) 0.36945(15) 0.0333(7) Uani 1 1 d . . . 
H21 H 0.8759 1.0195 0.3405 0.040 Uiso 1 1 calc R . . 
C7 C 0.6876(2) 1.3891(2) 0.10627(19) 0.0406(8) Uani 1 1 d . . . 
H7 H 0.6585 1.4496 0.1253 0.049 Uiso 1 1 calc R . . 
C28 C 0.4566(2) 1.2423(3) 0.0689(2) 0.0599(11) Uani 1 1 d . . . 
H28A H 0.4903 1.3129 0.0803 0.072 Uiso 1 1 calc R . . 
H28B H 0.4209 1.2453 0.0202 0.072 Uiso 1 1 calc R . . 
C17 C 0.8166(2) 0.6677(2) 0.23952(15) 0.0288(7) Uani 1 1 d . . . 
H17 H 0.8009 0.6041 0.2116 0.035 Uiso 1 1 calc R . . 
C22 C 0.8407(2) 0.9574(3) 0.43219(16) 0.0456(9) Uani 1 1 d . . . 
H22A H 0.7714 0.9519 0.4157 0.068 Uiso 1 1 calc R . . 
H22B H 0.8554 1.0271 0.4568 0.068 Uiso 1 1 calc R . . 
H22C H 0.8620 0.8965 0.4642 0.068 Uiso 1 1 calc R . . 
C3 C 0.77150(18) 1.2188(2) 0.11995(14) 0.0224(6) Uani 1 1 d . . . 
C2 C 0.9318(2) 1.0189(2) 0.21078(16) 0.0271(7) Uani 1 1 d . . . 
C1 C 0.91296(19) 1.1144(2) 0.17861(16) 0.0278(7) Uani 1 1 d . . . 
H2 H 0.9873(19) 0.988(2) 0.2270(13) 0.017(7) Uiso 1 1 d . . . 
H1 H 0.9535(19) 1.164(2) 0.1653(13) 0.023(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 
Br1 Al1 2.3199(9) . ? 
Al1 O1 1.8798(19) . ? 
Al1 B1 2.113(3) . ? 
Al1 Br2 2.3168(9) . ? 
O1 C27 1.477(3) . ? 
O1 C30 1.487(3) . ? 
N1 C1 1.403(3) . ? 
N1 C3 1.432(3) . ? 
N1 B1 1.438(4) . ? 
C27 C28 1.511(4) . ? 
N2 C2 1.402(3) . ? 
N2 C15 1.436(3) . ? 
N2 B1 1.437(4) . ? 
C11 C9 1.535(4) . ? 
C4 C5 1.392(5) . ? 
C4 C3 1.400(4) . ? 
C4 C12 1.523(4) . ? 
C12 C14 1.515(5) . ? 
C12 C13 1.531(4) . ? 
C6 C5 1.366(5) . ? 
C6 C7 1.380(5) . ? 
C29 C28 1.479(5) . ? 
C29 C30 1.497(5) . ? 
C15 C16 1.407(4) . ? 
C15 C20 1.407(4) . ? 
C26 C24 1.537(4) . ? 
C10 C9 1.528(4) . ? 
C23 C21 1.538(4) . ? 
C9 C8 1.513(4) . ? 
C20 C19 1.393(4) . ? 
C20 C21 1.516(4) . ? 
C19 C18 1.381(4) . ? 
C16 C17 1.391(4) . ? 
C16 C24 1.526(4) . ? 
C25 C24 1.523(4) . ? 
C18 C17 1.381(4) . ? 
C8 C7 1.389(4) . ? 
C8 C3 1.405(4) . ? 
C21 C22 1.531(4) . ? 
C2 C1 1.326(4) . ? 
 
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 
O1 Al1 B1 113.79(10) . . ? 
O1 Al1 Br2 100.51(6) . . ? 
B1 Al1 Br2 111.91(9) . . ? 
O1 Al1 Br1 100.19(7) . . ? 
B1 Al1 Br1 117.98(9) . . ? 
Br2 Al1 Br1 110.57(3) . . ? 
C27 O1 C30 108.5(2) . . ? 
C27 O1 Al1 121.61(15) . . ? 
C30 O1 Al1 125.50(17) . . ? 
C1 N1 C3 121.5(2) . . ? 
C1 N1 B1 108.9(2) . . ? 
C3 N1 B1 128.9(2) . . ? 
O1 C27 C28 103.3(2) . . ? 
C2 N2 C15 121.7(2) . . ? 
C2 N2 B1 109.1(2) . . ? 
C15 N2 B1 129.2(2) . . ? 
C5 C4 C3 117.6(3) . . ? 
C5 C4 C12 121.0(3) . . ? 
C3 C4 C12 121.4(3) . . ? 
C14 C12 C4 111.4(3) . . ? 
C14 C12 C13 111.5(3) . . ? 
C4 C12 C13 111.3(3) . . ? 
C5 C6 C7 120.5(3) . . ? 
C6 C5 C4 121.2(3) . . ? 
C28 C29 C30 105.5(3) . . ? 
C16 C15 C20 121.5(2) . . ? 
C16 C15 N2 119.1(2) . . ? 
C20 C15 N2 119.4(2) . . ? 
O1 C30 C29 105.3(2) . . ? 
C8 C9 C10 113.5(3) . . ? 
C8 C9 C11 110.3(2) . . ? 
C10 C9 C11 109.7(2) . . ? 
C19 C20 C15 117.9(2) . . ? 
C19 C20 C21 120.6(3) . . ? 
C15 C20 C21 121.5(2) . . ? 
C18 C19 C20 121.2(3) . . ? 
N2 B1 N1 103.4(2) . . ? 
N2 B1 Al1 125.80(19) . . ? 
N1 B1 Al1 130.4(2) . . ? 
C17 C16 C15 118.1(3) . . ? 
C17 C16 C24 120.6(2) . . ? 
C15 C16 C24 121.3(2) . . ? 
C25 C24 C16 114.3(2) . . ? 
C25 C24 C26 109.8(2) . . ? 
C16 C24 C26 110.1(2) . . ? 
C17 C18 C19 120.2(3) . . ? 
C7 C8 C3 117.2(3) . . ? 
C7 C8 C9 122.2(3) . . ? 
C3 C8 C9 120.6(2) . . ? 
C20 C21 C22 112.3(2) . . ? 
C20 C21 C23 110.5(2) . . ? 
C22 C21 C23 109.8(3) . . ? 
C6 C7 C8 121.3(3) . . ? 
C29 C28 C27 103.7(3) . . ? 
C18 C17 C16 121.1(3) . . ? 
C4 C3 C8 122.3(3) . . ? 
C4 C3 N1 118.5(2) . . ? 
C8 C3 N1 119.1(2) . . ? 
C1 C2 N2 109.3(3) . . ? 
C2 C1 N1 109.4(2) . . ? 
 
_diffrn_measured_fraction_theta_max    0.998 
_diffrn_reflns_theta_full              26.00 
_diffrn_measured_fraction_theta_full   0.998 
_refine_diff_density_max    0.577 
_refine_diff_density_min   -0.418 
_refine_diff_density_rms    0.068 
