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

 
data_cmpd2 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C30 H44 B Cl2 Ga N2 O' 
_chemical_formula_weight          600.10 
 
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' 
 'N'  'N'   0.0061   0.0033 
 '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' 
 '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' 
 'Cl'  'Cl'   0.1484   0.1585 
 '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) 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z' 
 
_cell_length_a                    10.2077(10) 
_cell_length_b                    12.3372(11) 
_cell_length_c                    13.3681(15) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  106.068(11) 
_cell_angle_gamma                 90.00 
_cell_volume                      1617.7(3) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     123(2) 
_cell_measurement_reflns_used     5006
_cell_measurement_theta_min       2.07
_cell_measurement_theta_max       29.17 
 
_exptl_crystal_description        'block' 
_exptl_crystal_colour             'colourless' 
_exptl_crystal_size_max           0.28 
_exptl_crystal_size_mid           0.21 
_exptl_crystal_size_min           0.15 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.232 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              632 
_exptl_absorpt_coefficient_mu     1.039 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.755 
_exptl_absorpt_correction_T_max   0.859 
_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             13178 
_diffrn_reflns_av_R_equivalents   0.0351 
_diffrn_reflns_av_sigmaI/netI     0.0470 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        12 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        16 
_diffrn_reflns_theta_min          2.94 
_diffrn_reflns_theta_max          25.50 
_reflns_number_total              5768 
_reflns_number_gt                 5327 
_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)+(0.0407P)²+0.1562P] 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_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    -0.003(9) 
_refine_ls_number_reflns          5768 
_refine_ls_number_parameters      350 
_refine_ls_number_restraints      13 
_refine_ls_R_factor_all           0.0398 
_refine_ls_R_factor_gt            0.0338 
_refine_ls_wR_factor_ref          0.0830 
_refine_ls_wR_factor_gt           0.0783 
_refine_ls_goodness_of_fit_ref    1.062 
_refine_ls_restrained_S_all       1.099 
_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 0.68008(3) 0.91996(2) 0.12262(2) 0.02628(10) Uani 1 1 d . . . 
Cl2 Cl 0.72664(8) 1.05074(7) 0.02457(7) 0.0349(2) Uani 1 1 d . . . 
Cl1 Cl 0.46282(8) 0.93894(8) 0.11614(8) 0.0482(3) Uani 1 1 d . . . 
N1 N 0.8994(3) 0.7929(2) 0.29816(19) 0.0262(6) Uani 1 1 d . . . 
N2 N 0.8497(3) 0.95732(19) 0.3528(2) 0.0284(6) Uani 1 1 d . . . 
C13 C 0.9754(4) 0.8081(3) 0.4021(3) 0.0317(8) Uani 1 1 d . . . 
C14 C 0.9445(3) 0.9059(3) 0.4340(2) 0.0330(8) Uani 1 1 d . . . 
C20 C 0.8482(3) 1.1545(3) 0.3284(2) 0.0300(7) Uani 1 1 d . . . 
C15 C 0.7957(3) 1.0637(3) 0.3668(2) 0.0310(7) Uani 1 1 d . . . 
C16 C 0.6953(4) 1.0702(3) 0.4194(3) 0.0374(8) Uani 1 1 d . . . 
B1 B 0.8185(4) 0.8879(3) 0.2643(3) 0.0260(8) Uani 1 1 d . . . 
C1 C 0.9168(3) 0.6984(2) 0.2393(2) 0.0254(7) Uani 1 1 d . . . 
C17 C 0.6497(4) 1.1742(3) 0.4357(3) 0.0418(9) Uani 1 1 d . . . 
H17 H 0.5817 1.1816 0.4714 0.050 Uiso 1 1 calc R . . 
C18 C 0.7003(4) 1.2649(3) 0.4017(3) 0.0422(9) Uani 1 1 d . . . 
H18 H 0.6697 1.3344 0.4161 0.051 Uiso 1 1 calc R . . 
C6 C 1.0332(4) 0.6912(3) 0.2037(3) 0.0338(8) Uani 1 1 d . . . 
C2 C 0.8148(3) 0.6174(3) 0.2173(2) 0.0300(7) Uani 1 1 d . . . 
C19 C 0.7962(4) 1.2564(3) 0.3462(3) 0.0374(8) Uani 1 1 d . . . 
H19 H 0.8274 1.3200 0.3199 0.045 Uiso 1 1 calc R . . 
C10 C 0.6900(3) 0.6254(3) 0.2589(3) 0.0367(8) Uani 1 1 d . . . 
H10 H 0.6519 0.7003 0.2444 0.044 Uiso 1 1 calc R . . 
C7 C 1.1397(4) 0.7817(3) 0.2241(3) 0.0401(8) Uani 1 1 d . . . 
H7 H 1.1337 0.8223 0.2874 0.048 Uiso 1 1 calc R . . 
C5 C 1.0452(4) 0.6015(3) 0.1439(3) 0.0463(10) Uani 1 1 d . . . 
H5 H 1.1238 0.5943 0.1195 0.056 Uiso 1 1 calc R . . 
C21 C 0.9578(4) 1.1453(3) 0.2707(3) 0.0340(8) Uani 1 1 d . . . 
H21 H 0.9399 1.0767 0.2294 0.041 Uiso 1 1 calc R . . 
C3 C 0.8325(4) 0.5307(3) 0.1564(3) 0.0390(8) Uani 1 1 d . . . 
H3 H 0.7652 0.4754 0.1398 0.047 Uiso 1 1 calc R . . 
C11 C 0.7294(4) 0.6079(4) 0.3771(3) 0.0503(10) Uani 1 1 d . . . 
H11A H 0.7784 0.5390 0.3941 0.075 Uiso 1 1 calc R . . 
H11B H 0.6468 0.6060 0.4008 0.075 Uiso 1 1 calc R . . 
H11C H 0.7882 0.6674 0.4117 0.075 Uiso 1 1 calc R . . 
C22 C 1.0991(4) 1.1351(4) 0.3470(3) 0.0478(10) Uani 1 1 d . . . 
H22A H 1.1188 1.1999 0.3911 0.072 Uiso 1 1 calc R . . 
H22B H 1.1674 1.1280 0.3083 0.072 Uiso 1 1 calc R . . 
H22C H 1.1021 1.0709 0.3907 0.072 Uiso 1 1 calc R . . 
C23 C 0.9543(4) 1.2382(3) 0.1934(3) 0.0479(10) Uani 1 1 d . . . 
H23A H 0.8602 1.2503 0.1516 0.072 Uiso 1 1 calc R . . 
H23B H 1.0108 1.2191 0.1475 0.072 Uiso 1 1 calc R . . 
H23C H 0.9898 1.3045 0.2318 0.072 Uiso 1 1 calc R . . 
C24 C 0.6317(5) 0.9708(3) 0.4550(3) 0.0570(12) Uani 1 1 d . . . 
H24 H 0.6625 0.9059 0.4229 0.068 Uiso 1 1 calc R . . 
O1 O 0.6609(2) 0.7984(2) 0.01972(19) 0.0391(6) Uani 1 1 d . . . 
C12 C 0.5772(4) 0.5451(3) 0.2074(4) 0.0530(10) Uani 1 1 d . . . 
H12A H 0.5505 0.5562 0.1318 0.079 Uiso 1 1 calc R . . 
H12B H 0.4981 0.5568 0.2341 0.079 Uiso 1 1 calc R . . 
H12C H 0.6107 0.4709 0.2231 0.079 Uiso 1 1 calc R . . 
C9 C 1.2859(4) 0.7361(4) 0.2452(3) 0.0549(11) Uani 1 1 d . . . 
H9A H 1.2971 0.7027 0.1815 0.082 Uiso 1 1 calc R . . 
H9B H 1.3015 0.6817 0.3006 0.082 Uiso 1 1 calc R . . 
H9C H 1.3519 0.7952 0.2667 0.082 Uiso 1 1 calc R . . 
C8 C 1.1114(4) 0.8609(3) 0.1338(4) 0.0554(11) Uani 1 1 d . . . 
H8A H 1.1187 0.8232 0.0710 0.083 Uiso 1 1 calc R . . 
H8B H 1.1779 0.9201 0.1503 0.083 Uiso 1 1 calc R . . 
H8C H 1.0192 0.8905 0.1218 0.083 Uiso 1 1 calc R . . 
C30 C 0.7614(4) 0.7785(4) -0.0355(4) 0.0619(12) Uani 1 1 d . . . 
H30A H 0.8400 0.7382 0.0088 0.074 Uiso 1 1 calc R . . 
H30B H 0.7945 0.8476 -0.0572 0.074 Uiso 1 1 calc R . . 
C4 C 0.9460(4) 0.5230(3) 0.1193(3) 0.0471(10) Uani 1 1 d . . . 
H4 H 0.9553 0.4633 0.0769 0.057 Uiso 1 1 calc R . . 
C25 C 0.4740(5) 0.9730(4) 0.4176(4) 0.0757(15) Uani 1 1 d . . . 
H25A H 0.4401 1.0334 0.4511 0.114 Uiso 1 1 calc R . . 
H25B H 0.4379 0.9046 0.4362 0.114 Uiso 1 1 calc R . . 
H25C H 0.4442 0.9825 0.3419 0.114 Uiso 1 1 calc R . . 
C26 C 0.6827(6) 0.9571(4) 0.5740(4) 0.0827(17) Uani 1 1 d . . . 
H26A H 0.7826 0.9559 0.5957 0.124 Uiso 1 1 calc R . . 
H26B H 0.6478 0.8889 0.5942 0.124 Uiso 1 1 calc R . . 
H26C H 0.6502 1.0178 0.6080 0.124 Uiso 1 1 calc R . . 
C27 C 0.5320(5) 0.7518(5) -0.0394(5) 0.095(2) Uani 1 1 d . . . 
H27A H 0.5154 0.6821 -0.0083 0.114 Uiso 1 1 calc R . . 
H27B H 0.4559 0.8018 -0.0403 0.114 Uiso 1 1 calc R . . 
C28 C 0.5432(6) 0.7350(4) -0.1439(4) 0.0832(17) Uani 1 1 d U . . 
H28A H 0.5146 0.8005 -0.1873 0.100 Uiso 1 1 calc R . . 
H28B H 0.4869 0.6728 -0.1776 0.100 Uiso 1 1 calc R . . 
C29 C 0.6897(7) 0.7129(6) -0.1279(5) 0.112(2) Uani 1 1 d U . . 
H29A H 0.7187 0.7348 -0.1898 0.134 Uiso 1 1 calc R . . 
H29B H 0.7093 0.6348 -0.1147 0.134 Uiso 1 1 calc R . . 
H14 H 0.981(4) 0.935(3) 0.500(3) 0.046(10) Uiso 1 1 d . . . 
H13 H 1.041(3) 0.753(3) 0.439(3) 0.033(9) 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 2.008(2) . ? 
Ga1 B1 2.064(4) . ? 
Ga1 Cl1 2.2078(8) . ? 
Ga1 Cl2 2.2118(9) . ? 
N1 C13 1.404(4) . ? 
N1 B1 1.433(4) . ? 
N1 C1 1.445(4) . ? 
N2 C14 1.392(4) . ? 
N2 B1 1.423(4) . ? 
N2 C15 1.456(4) . ? 
C13 C14 1.346(5) . ? 
C20 C15 1.399(5) . ? 
C20 C19 1.410(5) . ? 
C20 C21 1.529(5) . ? 
C15 C16 1.396(5) . ? 
C16 C17 1.403(5) . ? 
C16 C24 1.524(5) . ? 
C1 C6 1.399(5) . ? 
C1 C2 1.414(4) . ? 
C17 C18 1.362(5) . ? 
C18 C19 1.387(5) . ? 
C6 C5 1.390(5) . ? 
C6 C7 1.530(5) . ? 
C2 C3 1.386(5) . ? 
C2 C10 1.528(5) . ? 
C10 C12 1.531(5) . ? 
C10 C11 1.533(5) . ? 
C7 C8 1.516(5) . ? 
C7 C9 1.547(5) . ? 
C5 C4 1.374(5) . ? 
C21 C22 1.525(5) . ? 
C21 C23 1.537(5) . ? 
C3 C4 1.384(5) . ? 
C24 C26 1.541(7) . ? 
C24 C25 1.547(7) . ? 
O1 C30 1.441(5) . ? 
O1 C27 1.452(5) . ? 
C30 C29 1.489(7) . ? 
C27 C28 1.447(8) . ? 
C28 C29 1.476(8) . ? 
 
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 113.44(12) . . ? 
O1 Ga1 Cl1 98.39(7) . . ? 
B1 Ga1 Cl1 118.79(10) . . ? 
O1 Ga1 Cl2 97.77(8) . . ? 
B1 Ga1 Cl2 118.61(10) . . ? 
Cl1 Ga1 Cl2 106.12(4) . . ? 
C13 N1 B1 108.4(3) . . ? 
C13 N1 C1 121.9(3) . . ? 
B1 N1 C1 129.4(3) . . ? 
C14 N2 B1 108.7(3) . . ? 
C14 N2 C15 121.1(3) . . ? 
B1 N2 C15 130.1(3) . . ? 
C14 C13 N1 108.6(3) . . ? 
C13 C14 N2 109.6(3) . . ? 
C15 C20 C19 116.8(3) . . ? 
C15 C20 C21 122.3(3) . . ? 
C19 C20 C21 120.8(3) . . ? 
C16 C15 C20 123.2(3) . . ? 
C16 C15 N2 118.3(3) . . ? 
C20 C15 N2 118.5(3) . . ? 
C15 C16 C17 116.9(3) . . ? 
C15 C16 C24 123.1(3) . . ? 
C17 C16 C24 120.0(3) . . ? 
N2 B1 N1 104.7(3) . . ? 
N2 B1 Ga1 125.9(2) . . ? 
N1 B1 Ga1 129.4(2) . . ? 
C6 C1 C2 122.0(3) . . ? 
C6 C1 N1 118.7(3) . . ? 
C2 C1 N1 119.3(3) . . ? 
C18 C17 C16 121.8(3) . . ? 
C17 C18 C19 120.3(3) . . ? 
C5 C6 C1 117.7(3) . . ? 
C5 C6 C7 120.8(3) . . ? 
C1 C6 C7 121.4(3) . . ? 
C3 C2 C1 117.3(3) . . ? 
C3 C2 C10 121.4(3) . . ? 
C1 C2 C10 121.3(3) . . ? 
C18 C19 C20 120.8(3) . . ? 
C2 C10 C12 113.2(3) . . ? 
C2 C10 C11 111.0(3) . . ? 
C12 C10 C11 108.8(3) . . ? 
C8 C7 C6 111.0(3) . . ? 
C8 C7 C9 109.9(3) . . ? 
C6 C7 C9 111.7(3) . . ? 
C4 C5 C6 121.5(3) . . ? 
C22 C21 C20 110.9(3) . . ? 
C22 C21 C23 110.7(3) . . ? 
C20 C21 C23 113.6(3) . . ? 
C4 C3 C2 121.5(3) . . ? 
C16 C24 C26 111.0(4) . . ? 
C16 C24 C25 112.3(4) . . ? 
C26 C24 C25 111.1(4) . . ? 
C30 O1 C27 108.6(3) . . ? 
C30 O1 Ga1 122.0(2) . . ? 
C27 O1 Ga1 124.8(3) . . ? 
O1 C30 C29 105.2(4) . . ? 
C5 C4 C3 120.0(3) . . ? 
C28 C27 O1 106.3(4) . . ? 
C27 C28 C29 103.5(4) . . ? 
C28 C29 C30 105.3(5) . . ? 
 
_diffrn_measured_fraction_theta_max    0.998 
_diffrn_reflns_theta_full              25.50 
_diffrn_measured_fraction_theta_full   0.998 
_refine_diff_density_max    0.386 
_refine_diff_density_min   -0.325 
_refine_diff_density_rms    0.050 
