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

 
data_cmpd3 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C30 H44 B Br2 Ga N2 O' 
_chemical_formula_weight          689.02 
 
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' 
 'Ga'  'Ga'   0.2307   1.6083 
 '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' 
 
_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                    14.1260(7) 
_cell_length_b                    12.1475(6) 
_cell_length_c                    19.3683(11) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  100.037(5) 
_cell_angle_gamma                 90.00 
_cell_volume                      3272.6(3) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     123(2) 
_cell_measurement_reflns_used     6818
_cell_measurement_theta_min       1.98
_cell_measurement_theta_max       29.12 
 
_exptl_crystal_description        'block' 
_exptl_crystal_colour             'colourless' 
_exptl_crystal_size_max           0.38 
_exptl_crystal_size_mid           0.28 
_exptl_crystal_size_min           0.21 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.398 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1408 
_exptl_absorpt_coefficient_mu     3.306 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.362 
_exptl_absorpt_correction_T_max   0.543 
_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             22256 
_diffrn_reflns_av_R_equivalents   0.0355 
_diffrn_reflns_av_sigmaI/netI     0.0404 
_diffrn_reflns_limit_h_min        -17 
_diffrn_reflns_limit_h_max        15 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        -23 
_diffrn_reflns_limit_l_max        23 
_diffrn_reflns_theta_min          2.93 
_diffrn_reflns_theta_max          25.50 
_reflns_number_total              6093 
_reflns_number_gt                 4781 
_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)+(0.0313P)²+0.9897P] 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          6093 
_refine_ls_number_parameters      350 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0494 
_refine_ls_R_factor_gt            0.0314 
_refine_ls_wR_factor_ref          0.0725 
_refine_ls_wR_factor_gt           0.0660 
_refine_ls_goodness_of_fit_ref    1.029 
_refine_ls_restrained_S_all       1.029 
_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 
Ga1 Ga 0.128080(19) 0.50860(2) 0.195695(15) 0.02104(9) Uani 1 1 d . . . 
Br1 Br 0.09574(2) 0.52331(3) 0.310025(16) 0.04155(10) Uani 1 1 d . . . 
Br2 Br 0.04180(2) 0.35999(2) 0.139061(18) 0.03981(10) Uani 1 1 d . . . 
N2 N 0.31519(14) 0.62744(16) 0.16296(11) 0.0186(5) Uani 1 1 d . . . 
O1 O 0.04122(11) 0.63003(14) 0.15214(9) 0.0240(4) Uani 1 1 d . . . 
C1 C 0.34515(17) 0.35911(19) 0.25040(13) 0.0191(5) Uani 1 1 d . . . 
N1 N 0.34780(14) 0.46507(16) 0.21817(11) 0.0191(5) Uani 1 1 d . . . 
C6 C 0.32094(17) 0.2665(2) 0.20753(13) 0.0213(6) Uani 1 1 d . . . 
C25 C 0.41466(19) 0.6121(2) 0.17793(14) 0.0250(6) Uani 1 1 d . . . 
C2 C 0.36491(17) 0.3507(2) 0.32361(14) 0.0229(6) Uani 1 1 d . . . 
B1 B 0.2702(2) 0.5350(2) 0.18842(15) 0.0184(6) Uani 1 1 d . . . 
C26 C 0.43404(19) 0.5166(2) 0.21089(15) 0.0244(6) Uani 1 1 d . . . 
C13 C 0.27275(17) 0.7160(2) 0.11928(13) 0.0194(5) Uani 1 1 d . . . 
C10 C 0.3952(2) 0.4500(2) 0.36978(14) 0.0299(6) Uani 1 1 d . . . 
H10 H 0.3793 0.5176 0.3406 0.036 Uiso 1 1 calc R . . 
C4 C 0.33404(19) 0.1562(2) 0.31244(15) 0.0287(6) Uani 1 1 d . . . 
H4 H 0.3291 0.0865 0.3338 0.034 Uiso 1 1 calc R . . 
C3 C 0.35933(18) 0.2475(2) 0.35338(14) 0.0258(6) Uani 1 1 d . . . 
H3 H 0.3732 0.2399 0.4029 0.031 Uiso 1 1 calc R . . 
C28 C 0.0269(2) 0.6475(3) 0.07653(15) 0.0362(7) Uani 1 1 d . . . 
H28A H 0.0006 0.5808 0.0507 0.043 Uiso 1 1 calc R . . 
H28B H 0.0878 0.6685 0.0612 0.043 Uiso 1 1 calc R . . 
C8 C 0.2480(2) 0.1808(2) 0.08992(15) 0.0329(7) Uani 1 1 d . . . 
H8A H 0.2847 0.1122 0.0980 0.049 Uiso 1 1 calc R . . 
H8B H 0.2342 0.1966 0.0395 0.049 Uiso 1 1 calc R . . 
H8C H 0.1874 0.1732 0.1077 0.049 Uiso 1 1 calc R . . 
C11 C 0.3418(2) 0.4566(3) 0.43174(16) 0.0418(8) Uani 1 1 d . . . 
H11A H 0.2725 0.4492 0.4148 0.063 Uiso 1 1 calc R . . 
H11B H 0.3549 0.5277 0.4553 0.063 Uiso 1 1 calc R . . 
H11C H 0.3636 0.3970 0.4649 0.063 Uiso 1 1 calc R . . 
C7 C 0.30647(19) 0.2749(2) 0.12807(14) 0.0270(6) Uani 1 1 d . . . 
H7 H 0.2705 0.3446 0.1143 0.032 Uiso 1 1 calc R . . 
C5 C 0.31570(18) 0.1655(2) 0.24016(14) 0.0256(6) Uani 1 1 d . . . 
H5 H 0.2992 0.1017 0.2124 0.031 Uiso 1 1 calc R . . 
C29 C -0.0451(2) 0.7414(3) 0.06573(19) 0.0570(10) Uani 1 1 d . . . 
H29A H -0.0124 0.8134 0.0750 0.068 Uiso 1 1 calc R . . 
H29B H -0.0819 0.7413 0.0173 0.068 Uiso 1 1 calc R . . 
C12 C 0.5038(2) 0.4486(3) 0.39579(17) 0.0453(8) Uani 1 1 d . . . 
H12A H 0.5208 0.3845 0.4261 0.068 Uiso 1 1 calc R . . 
H12B H 0.5230 0.5160 0.4224 0.068 Uiso 1 1 calc R . . 
H12C H 0.5372 0.4444 0.3556 0.068 Uiso 1 1 calc R . . 
C27 C -0.0482(2) 0.6604(3) 0.17674(17) 0.0394(8) Uani 1 1 d . . . 
H27A H -0.0343 0.7089 0.2183 0.047 Uiso 1 1 calc R . . 
H27B H -0.0819 0.5938 0.1894 0.047 Uiso 1 1 calc R . . 
C30 C -0.1083(2) 0.7195(3) 0.11672(18) 0.0501(9) Uani 1 1 d . . . 
H30A H -0.1634 0.6733 0.0954 0.060 Uiso 1 1 calc R . . 
H30B H -0.1332 0.7893 0.1329 0.060 Uiso 1 1 calc R . . 
C14 C 0.23119(17) 0.8042(2) 0.14962(14) 0.0234(6) Uani 1 1 d . . . 
C22 C 0.23403(18) 0.8090(2) 0.22795(14) 0.0277(6) Uani 1 1 d . . . 
H22 H 0.2218 0.7330 0.2440 0.033 Uiso 1 1 calc R . . 
C24 C 0.3344(2) 0.8434(2) 0.26524(16) 0.0368(7) Uani 1 1 d . . . 
H24A H 0.3818 0.7896 0.2551 0.055 Uiso 1 1 calc R . . 
H24B H 0.3354 0.8463 0.3159 0.055 Uiso 1 1 calc R . . 
H24C H 0.3500 0.9161 0.2485 0.055 Uiso 1 1 calc R . . 
C18 C 0.27292(19) 0.7095(2) 0.04736(14) 0.0305(7) Uani 1 1 d . . . 
C15 C 0.1883(2) 0.8864(2) 0.10487(17) 0.0383(8) Uani 1 1 d . . . 
H15 H 0.1585 0.9469 0.1236 0.046 Uiso 1 1 calc R . . 
C23 C 0.1584(2) 0.8844(3) 0.24985(18) 0.0457(8) Uani 1 1 d . . . 
H23A H 0.1738 0.9611 0.2407 0.069 Uiso 1 1 calc R . . 
H23B H 0.1577 0.8748 0.3000 0.069 Uiso 1 1 calc R . . 
H23C H 0.0951 0.8659 0.2229 0.069 Uiso 1 1 calc R . . 
C17 C 0.2297(2) 0.7948(3) 0.00557(16) 0.0473(9) Uani 1 1 d . . . 
H17 H 0.2291 0.7928 -0.0436 0.057 Uiso 1 1 calc R . . 
C9 C 0.4029(2) 0.2836(3) 0.10331(16) 0.0420(8) Uani 1 1 d . . . 
H9A H 0.4378 0.3483 0.1247 0.063 Uiso 1 1 calc R . . 
H9B H 0.3921 0.2908 0.0521 0.063 Uiso 1 1 calc R . . 
H9C H 0.4409 0.2172 0.1172 0.063 Uiso 1 1 calc R . . 
C16 C 0.1881(2) 0.8818(3) 0.03395(19) 0.0519(10) Uani 1 1 d . . . 
H16 H 0.1589 0.9392 0.0044 0.062 Uiso 1 1 calc R . . 
C19 C 0.3150(2) 0.6112(3) 0.01485(16) 0.0445(8) Uani 1 1 d . . . 
H19 H 0.3422 0.5603 0.0539 0.053 Uiso 1 1 calc R . . 
C20 C 0.3975(3) 0.6463(4) -0.0219(2) 0.0779(14) Uani 1 1 d . . . 
H20A H 0.3733 0.6976 -0.0600 0.117 Uiso 1 1 calc R . . 
H20B H 0.4246 0.5813 -0.0412 0.117 Uiso 1 1 calc R . . 
H20C H 0.4475 0.6826 0.0119 0.117 Uiso 1 1 calc R . . 
C21 C 0.2384(3) 0.5482(4) -0.0341(2) 0.0801(14) Uani 1 1 d . . . 
H21A H 0.1895 0.5216 -0.0079 0.120 Uiso 1 1 calc R . . 
H21B H 0.2678 0.4854 -0.0540 0.120 Uiso 1 1 calc R . . 
H21C H 0.2082 0.5969 -0.0720 0.120 Uiso 1 1 calc R . . 
H25 H 0.4550(18) 0.665(2) 0.1662(13) 0.019(7) Uiso 1 1 d . . . 
H26 H 0.4914(19) 0.4843(19) 0.2269(13) 0.020(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 
Ga1 O1 2.0081(16) . ? 
Ga1 B1 2.061(3) . ? 
Ga1 Br2 2.3412(4) . ? 
Ga1 Br1 2.3445(4) . ? 
N2 C25 1.397(3) . ? 
N2 B1 1.420(3) . ? 
N2 C13 1.434(3) . ? 
O1 C28 1.459(3) . ? 
O1 C27 1.473(3) . ? 
C1 C2 1.400(3) . ? 
C1 C6 1.404(3) . ? 
C1 N1 1.434(3) . ? 
N1 C26 1.399(3) . ? 
N1 B1 1.427(3) . ? 
C6 C5 1.388(4) . ? 
C6 C7 1.520(4) . ? 
C25 C26 1.329(4) . ? 
C2 C3 1.387(4) . ? 
C2 C10 1.518(4) . ? 
C13 C18 1.396(4) . ? 
C13 C14 1.400(4) . ? 
C10 C11 1.527(4) . ? 
C10 C12 1.530(4) . ? 
C4 C3 1.374(4) . ? 
C4 C5 1.383(4) . ? 
C28 C29 1.519(4) . ? 
C8 C7 1.524(4) . ? 
C7 C9 1.525(4) . ? 
C29 C30 1.466(5) . ? 
C27 C30 1.498(4) . ? 
C14 C15 1.390(4) . ? 
C14 C22 1.512(4) . ? 
C22 C23 1.522(4) . ? 
C22 C24 1.532(4) . ? 
C18 C17 1.389(4) . ? 
C18 C19 1.518(4) . ? 
C15 C16 1.374(5) . ? 
C17 C16 1.369(5) . ? 
C19 C21 1.516(4) . ? 
C19 C20 1.529(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 Ga1 B1 112.81(9) . . ? 
O1 Ga1 Br2 98.02(5) . . ? 
B1 Ga1 Br2 121.44(8) . . ? 
O1 Ga1 Br1 97.78(5) . . ? 
B1 Ga1 Br1 113.89(8) . . ? 
Br2 Ga1 Br1 109.274(16) . . ? 
C25 N2 B1 108.5(2) . . ? 
C25 N2 C13 121.7(2) . . ? 
B1 N2 C13 129.1(2) . . ? 
C28 O1 C27 108.17(19) . . ? 
C28 O1 Ga1 119.76(15) . . ? 
C27 O1 Ga1 122.94(15) . . ? 
C2 C1 C6 121.7(2) . . ? 
C2 C1 N1 119.4(2) . . ? 
C6 C1 N1 118.9(2) . . ? 
C26 N1 B1 108.3(2) . . ? 
C26 N1 C1 122.4(2) . . ? 
B1 N1 C1 129.3(2) . . ? 
C5 C6 C1 117.7(2) . . ? 
C5 C6 C7 120.8(2) . . ? 
C1 C6 C7 121.4(2) . . ? 
C26 C25 N2 109.4(2) . . ? 
C3 C2 C1 118.1(2) . . ? 
C3 C2 C10 120.2(2) . . ? 
C1 C2 C10 121.6(2) . . ? 
N2 B1 N1 104.6(2) . . ? 
N2 B1 Ga1 130.34(19) . . ? 
N1 B1 Ga1 124.64(19) . . ? 
C25 C26 N1 109.2(2) . . ? 
C18 C13 C14 122.4(2) . . ? 
C18 C13 N2 118.2(2) . . ? 
C14 C13 N2 119.3(2) . . ? 
C2 C10 C11 112.2(2) . . ? 
C2 C10 C12 110.4(2) . . ? 
C11 C10 C12 110.3(2) . . ? 
C3 C4 C5 120.1(2) . . ? 
C4 C3 C2 121.1(2) . . ? 
O1 C28 C29 102.7(2) . . ? 
C6 C7 C8 114.0(2) . . ? 
C6 C7 C9 110.7(2) . . ? 
C8 C7 C9 109.8(2) . . ? 
C4 C5 C6 121.2(2) . . ? 
C30 C29 C28 104.0(3) . . ? 
O1 C27 C30 105.7(2) . . ? 
C29 C30 C27 106.4(3) . . ? 
C15 C14 C13 117.2(3) . . ? 
C15 C14 C22 122.0(3) . . ? 
C13 C14 C22 120.7(2) . . ? 
C14 C22 C23 113.9(2) . . ? 
C14 C22 C24 110.1(2) . . ? 
C23 C22 C24 110.0(2) . . ? 
C17 C18 C13 117.6(3) . . ? 
C17 C18 C19 120.6(3) . . ? 
C13 C18 C19 121.8(3) . . ? 
C16 C15 C14 121.2(3) . . ? 
C16 C17 C18 121.1(3) . . ? 
C17 C16 C15 120.5(3) . . ? 
C21 C19 C18 111.6(3) . . ? 
C21 C19 C20 111.6(3) . . ? 
C18 C19 C20 111.0(3) . . ? 
 
_diffrn_measured_fraction_theta_max    0.998 
_diffrn_reflns_theta_full              25.50 
_diffrn_measured_fraction_theta_full   0.998 
_refine_diff_density_max    0.463 
_refine_diff_density_min   -0.351 
_refine_diff_density_rms    0.068 
