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

####################################################################### 
# 
# 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_test1
_database_code_depnum_ccdc_archive 'CCDC 1409304'
_audit_update_record             
;
2015-06-27 deposited with the CCDC.
2016-10-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H27 B F2 N2 O2'
_chemical_formula_weight         424.29

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3457(12)
_cell_length_b                   8.8632(14)
_cell_length_c                   15.254(2)
_cell_angle_alpha                87.065(4)
_cell_angle_beta                 88.132(5)
_cell_angle_gamma                68.586(4)
_cell_volume                     1049.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2276
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      26.33

_exptl_crystal_description       DIAMOND
_exptl_crystal_colour            PINK
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9716
_exptl_absorpt_correction_T_max  0.9847
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11942
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_sigmaI/netI    0.0634
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.34
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3684
_reflns_number_gt                2504
_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, 2008)'
_computing_molecular_graphics    'MERCURY 3.2'
_computing_publication_material  'ORTEP 3V.2'

_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)+(0.1000P)²+0.3881P] 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         3684
_refine_ls_number_parameters     288
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.1690
_refine_ls_wR_factor_gt          0.1469
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_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
B1 B 0.3708(4) 0.4278(4) 0.4018(2) 0.0224(7) Uani 1 1 d . . .
F1 F 0.3894(2) 0.3929(2) 0.49096(10) 0.0310(5) Uani 1 1 d . . .
F2 F 0.2408(2) 0.3790(2) 0.37209(12) 0.0319(5) Uani 1 1 d . . .
N2 N 0.5399(3) 0.3391(3) 0.35124(14) 0.0205(6) Uani 1 1 d . . .
N1 N 0.3235(3) 0.6118(3) 0.38010(14) 0.0204(6) Uani 1 1 d . . .
C7 C 0.5509(3) 0.5785(3) 0.27027(17) 0.0191(6) Uani 1 1 d . . .
C8 C 0.6186(3) 0.4121(3) 0.28805(17) 0.0194(6) Uani 1 1 d . . .
C6 C 0.4047(3) 0.6796(3) 0.31548(18) 0.0189(6) Uani 1 1 d . . .
C12 C 0.7651(3) 0.2854(3) 0.25267(18) 0.0217(7) Uani 1 1 d . . .
C10 C 0.6308(4) 0.1787(3) 0.35543(19) 0.0227(7) Uani 1 1 d . . .
C4 C 0.3192(4) 0.8502(3) 0.31361(19) 0.0230(7) Uani 1 1 d . . .
C2 C 0.1982(4) 0.7336(4) 0.41819(18) 0.0242(7) Uani 1 1 d . . .
C9 C 0.5847(4) 0.0665(4) 0.4188(2) 0.0315(8) Uani 1 1 d . . .
H9A H 0.6145 0.0819 0.4771 0.047 Uiso 1 1 calc R . .
H9B H 0.6467 -0.0436 0.4035 0.047 Uiso 1 1 calc R . .
H9C H 0.4633 0.0892 0.4166 0.047 Uiso 1 1 calc R . .
C13 C 0.8950(4) 0.2958(4) 0.1848(2) 0.0279(7) Uani 1 1 d . . .
H13A H 0.9713 0.3401 0.2100 0.042 Uiso 1 1 calc R . .
H13B H 0.8369 0.3646 0.1361 0.042 Uiso 1 1 calc R . .
H13C H 0.9600 0.1893 0.1650 0.042 Uiso 1 1 calc R . .
C3 C 0.1926(4) 0.8813(4) 0.37813(19) 0.0258(7) Uani 1 1 d . . .
H3 H 0.1162 0.9835 0.3926 0.031 Uiso 1 1 calc R . .
C5 C 0.3512(4) 0.9764(3) 0.2533(2) 0.0288(7) Uani 1 1 d . . .
H5A H 0.3150 0.9686 0.1951 0.043 Uiso 1 1 calc R . .
H5B H 0.4717 0.9588 0.2521 0.043 Uiso 1 1 calc R . .
H5C H 0.2871 1.0824 0.2741 0.043 Uiso 1 1 calc R . .
C11 C 0.7683(4) 0.1443(3) 0.29554(19) 0.0236(7) Uani 1 1 d . . .
H11 H 0.8495 0.0416 0.2861 0.028 Uiso 1 1 calc R . .
C1 C 0.0893(4) 0.7065(4) 0.4930(2) 0.0315(8) Uani 1 1 d . . .
H1A H 0.0577 0.6155 0.4819 0.047 Uiso 1 1 calc R . .
H1B H -0.0127 0.8016 0.4988 0.047 Uiso 1 1 calc R . .
H1C H 0.1533 0.6851 0.5464 0.047 Uiso 1 1 calc R . .
C16 C 0.6613(3) 0.7378(3) 0.05027(18) 0.0202(6) Uani 1 1 d . . .
C19 C 0.7890(3) 0.6772(3) 0.22548(18) 0.0205(6) Uani 1 1 d . . .
C18 C 0.8764(3) 0.7325(3) 0.15769(19) 0.0209(6) Uani 1 1 d . . .
C15 C 0.5794(3) 0.6841(3) 0.11763(18) 0.0213(6) Uani 1 1 d . . .
H15 H 0.4780 0.6690 0.1055 0.026 Uiso 1 1 calc R . .
C17 C 0.8129(4) 0.7613(3) 0.07128(19) 0.0226(7) Uani 1 1 d . . .
C14 C 0.6411(3) 0.6507(3) 0.20408(18) 0.0181(6) Uani 1 1 d . . .
C24 C 1.0354(4) 0.7566(4) 0.1752(2) 0.0275(7) Uani 1 1 d . . .
H24 H 1.0783 0.7320 0.2318 0.033 Uiso 1 1 calc R . .
C20 C 0.8537(4) 0.6459(4) 0.31825(18) 0.0253(7) Uani 1 1 d . . .
H20A H 0.7646 0.6370 0.3572 0.038 Uiso 1 1 calc R . .
H20B H 0.8856 0.7341 0.3348 0.038 Uiso 1 1 calc R . .
H20C H 0.9522 0.5467 0.3218 0.038 Uiso 1 1 calc R . .
C21 C 0.5983(4) 0.7687(4) -0.04355(18) 0.0281(7) Uani 1 1 d . . .
H21 H 0.6178 0.8656 -0.0673 0.034 Uiso 1 1 calc R . .
O1 O 1.1174(3) 0.8073(3) 0.12033(15) 0.0359(6) Uani 1 1 d . . .
O2 O 0.8968(3) 0.8114(3) 0.00551(13) 0.0313(5) Uani 1 1 d . . .
H2 H 0.9802 0.8254 0.0253 0.047 Uiso 1 1 calc R . .
C23 C 0.4074(4) 0.8006(4) -0.0509(2) 0.0358(8) Uani 1 1 d . . .
H23A H 0.3876 0.7015 -0.0386 0.054 Uiso 1 1 calc R . .
H23B H 0.3703 0.8410 -0.1093 0.054 Uiso 1 1 calc R . .
H23C H 0.3437 0.8795 -0.0095 0.054 Uiso 1 1 calc R . .
C22 C 0.7043(4) 0.6270(4) -0.0994(2) 0.0377(8) Uani 1 1 d . . .
H22A H 0.8242 0.6105 -0.0955 0.056 Uiso 1 1 calc R . .
H22B H 0.6693 0.6509 -0.1594 0.056 Uiso 1 1 calc R . .
H22C H 0.6861 0.5305 -0.0783 0.056 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
B1 F1 1.381(4) . ?
B1 F2 1.401(4) . ?
B1 N2 1.544(4) . ?
B1 N1 1.551(4) . ?
N2 C10 1.345(4) . ?
N2 C8 1.409(3) . ?
N1 C2 1.341(4) . ?
N1 C6 1.409(3) . ?
C7 C8 1.389(4) . ?
C7 C6 1.406(4) . ?
C7 C14 1.494(4) . ?
C8 C12 1.436(4) . ?
C6 C4 1.416(4) . ?
C12 C11 1.374(4) . ?
C12 C13 1.498(4) . ?
C10 C11 1.396(4) . ?
C10 C9 1.492(4) . ?
C4 C3 1.382(4) . ?
C4 C5 1.505(4) . ?
C2 C3 1.402(4) . ?
C2 C1 1.500(4) . ?
C16 C15 1.375(4) . ?
C16 C17 1.404(4) . ?
C16 C21 1.518(4) . ?
C19 C14 1.389(4) . ?
C19 C18 1.415(4) . ?
C19 C20 1.507(4) . ?
C18 C17 1.413(4) . ?
C18 C24 1.454(4) . ?
C15 C14 1.409(4) . ?
C17 O2 1.352(3) . ?
C24 O1 1.234(3) . ?
C21 C23 1.520(4) . ?
C21 C22 1.528(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
F1 B1 F2 108.9(2) . . ?
F1 B1 N2 111.3(2) . . ?
F2 B1 N2 109.2(3) . . ?
F1 B1 N1 111.3(3) . . ?
F2 B1 N1 109.4(2) . . ?
N2 B1 N1 106.7(2) . . ?
C10 N2 C8 108.3(2) . . ?
C10 N2 B1 126.2(2) . . ?
C8 N2 B1 125.4(2) . . ?
C2 N1 C6 108.0(2) . . ?
C2 N1 B1 126.5(2) . . ?
C6 N1 B1 125.5(2) . . ?
C8 C7 C6 121.5(2) . . ?
C8 C7 C14 118.6(2) . . ?
C6 C7 C14 119.9(2) . . ?
C7 C8 N2 120.6(2) . . ?
C7 C8 C12 132.1(2) . . ?
N2 C8 C12 107.4(2) . . ?
C7 C6 N1 119.8(2) . . ?
C7 C6 C4 132.1(3) . . ?
N1 C6 C4 108.0(2) . . ?
C11 C12 C8 105.8(2) . . ?
C11 C12 C13 124.5(3) . . ?
C8 C12 C13 129.7(3) . . ?
N2 C10 C11 109.0(2) . . ?
N2 C10 C9 121.8(3) . . ?
C11 C10 C9 129.2(3) . . ?
C3 C4 C6 106.1(2) . . ?
C3 C4 C5 125.2(3) . . ?
C6 C4 C5 128.7(3) . . ?
N1 C2 C3 109.1(2) . . ?
N1 C2 C1 122.7(3) . . ?
C3 C2 C1 128.2(3) . . ?
C4 C3 C2 108.8(3) . . ?
C12 C11 C10 109.5(3) . . ?
C15 C16 C17 116.7(3) . . ?
C15 C16 C21 123.6(2) . . ?
C17 C16 C21 119.7(2) . . ?
C14 C19 C18 118.0(3) . . ?
C14 C19 C20 120.4(2) . . ?
C18 C19 C20 121.6(2) . . ?
C17 C18 C19 120.5(2) . . ?
C17 C18 C24 118.9(3) . . ?
C19 C18 C24 120.6(3) . . ?
C16 C15 C14 123.5(3) . . ?
O2 C17 C16 117.5(3) . . ?
O2 C17 C18 121.1(3) . . ?
C16 C17 C18 121.4(2) . . ?
C19 C14 C15 119.9(2) . . ?
C19 C14 C7 121.0(2) . . ?
C15 C14 C7 119.0(2) . . ?
O1 C24 C18 124.6(3) . . ?
C16 C21 C23 113.4(2) . . ?
C16 C21 C22 110.0(3) . . ?
C23 C21 C22 110.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.070
