# Electronic Supplementary Material (ESI) for ChemComm.
# 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_FcBpin(6)
_database_code_depnum_ccdc_archive 'CCDC 1028777'
_audit_update_record             
;
2014-10-13 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H21 B Fe O2'
_chemical_formula_weight         311.99

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   12.7414(5)
_cell_length_b                   7.5452(3)
_cell_length_c                   15.8499(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.524(3)
_cell_angle_gamma                90.00
_cell_volume                     1475.06(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    56555
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      30.51

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            'translucent light orange'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    1.019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.697
_exptl_absorpt_correction_T_max  0.876
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_special_details           'crystal-to-detector distance 30 mm'
_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  'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method       
'two φ and six ω scans with 2° steps (491 frames)'
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            56555
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         30.51
_reflns_number_total             4496
_reflns_number_gt                3693
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL2000 (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)'

_refine_special_details          
;
 Structure solved by direct methods and subsequent Fourier-difference
 synthesis. All non-hydrogen atoms were refined with anisotropic
 displacement parameters. The H atoms were introduced at calculated
 positions and were treated as riding atoms with an isotropic displacement
 parameter equal to 1.2 times that of the parent atom (1.5 for CH₃). 
 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)+(0.0458P)²+0.0655P] 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_number_reflns         4496
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0823
_refine_ls_wR_factor_gt          0.0787
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.51
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.098

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
Fe Fe 0.386384(13) 0.19618(2) 0.144210(11) 0.02346(7) Uani 1 1 d . . .
B1 B 0.23720(11) 0.08734(19) -0.03318(9) 0.0256(3) Uani 1 1 d . . .
O1 O 0.12917(7) 0.05375(12) -0.04328(6) 0.02936(19) Uani 1 1 d . . .
O2 O 0.28786(7) -0.03499(12) -0.07305(6) 0.0301(2) Uani 1 1 d . . .
C1 C 0.10658(10) -0.12328(16) -0.08083(8) 0.0246(2) Uani 1 1 d . . .
C2 C 0.20559(10) -0.15710(17) -0.12136(8) 0.0256(2) Uani 1 1 d . . .
C3 C -0.00313(10) -0.11769(19) -0.14604(9) 0.0330(3) Uani 1 1 d . . .
H3A H -0.0596 -0.0939 -0.1154 0.050 Uiso 1 1 calc R . .
H3B H -0.0173 -0.2320 -0.1761 0.050 Uiso 1 1 calc R . .
H3C H -0.0034 -0.0236 -0.1887 0.050 Uiso 1 1 calc R . .
C4 C 0.10306(11) -0.2477(2) -0.00593(9) 0.0349(3) Uani 1 1 d . . .
H4A H 0.1726 -0.2434 0.0379 0.052 Uiso 1 1 calc R . .
H4B H 0.0894 -0.3690 -0.0281 0.052 Uiso 1 1 calc R . .
H4C H 0.0449 -0.2109 0.0206 0.052 Uiso 1 1 calc R . .
C5 C 0.18347(12) -0.1060(2) -0.21699(9) 0.0351(3) Uani 1 1 d . . .
H5A H 0.1540 0.0146 -0.2250 0.053 Uiso 1 1 calc R . .
H5B H 0.1310 -0.1888 -0.2521 0.053 Uiso 1 1 calc R . .
H5C H 0.2512 -0.1108 -0.2356 0.053 Uiso 1 1 calc R . .
C6 C 0.25251(12) -0.34270(19) -0.10745(9) 0.0343(3) Uani 1 1 d . . .
H6A H 0.3153 -0.3512 -0.1325 0.051 Uiso 1 1 calc R . .
H6B H 0.1974 -0.4287 -0.1360 0.051 Uiso 1 1 calc R . .
H6C H 0.2752 -0.3681 -0.0449 0.051 Uiso 1 1 calc R . .
C7 C 0.29604(10) 0.24595(18) 0.02046(8) 0.0263(2) Uani 1 1 d . . .
C8 C 0.25549(10) 0.34631(16) 0.08238(8) 0.0272(2) Uani 1 1 d . . .
H8 H 0.1842 0.3391 0.0904 0.033 Uiso 1 1 calc R . .
C9 C 0.33937(10) 0.45821(16) 0.12965(8) 0.0283(3) Uani 1 1 d . . .
H9 H 0.3342 0.5378 0.1749 0.034 Uiso 1 1 calc R . .
C10 C 0.43264(11) 0.43014(17) 0.09727(8) 0.0297(3) Uani 1 1 d . . .
H10 H 0.5005 0.4885 0.1168 0.036 Uiso 1 1 calc R . .
C11 C 0.40656(10) 0.29941(16) 0.03057(8) 0.0283(3) Uani 1 1 d . . .
H11 H 0.4543 0.2550 -0.0018 0.034 Uiso 1 1 calc R . .
C12 C 0.40038(11) -0.07310(18) 0.15421(9) 0.0322(3) Uani 1 1 d . . .
H12 H 0.3786 -0.1555 0.1078 0.039 Uiso 1 1 calc R . .
C13 C 0.33472(11) -0.00925(18) 0.20815(9) 0.0346(3) Uani 1 1 d . . .
H13 H 0.2615 -0.0412 0.2041 0.042 Uiso 1 1 calc R . .
C14 C 0.39826(12) 0.11109(19) 0.26919(9) 0.0362(3) Uani 1 1 d . . .
H14 H 0.3748 0.1739 0.3131 0.043 Uiso 1 1 calc R . .
C15 C 0.50263(12) 0.12099(19) 0.25314(9) 0.0357(3) Uani 1 1 d . . .
H15 H 0.5614 0.1912 0.2846 0.043 Uiso 1 1 calc R . .
C16 C 0.50402(11) 0.00738(18) 0.18170(9) 0.0334(3) Uani 1 1 d . . .
H16 H 0.5637 -0.0112 0.1569 0.040 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
Fe C11 2.0370(12) . ?
Fe C12 2.0423(13) . ?
Fe C7 2.0447(12) . ?
Fe C16 2.0450(13) . ?
Fe C13 2.0489(13) . ?
Fe C8 2.0507(12) . ?
Fe C14 2.0516(13) . ?
Fe C15 2.0527(14) . ?
Fe C10 2.0584(12) . ?
Fe C9 2.0620(12) . ?
B1 O1 1.3689(16) . ?
B1 O2 1.3684(17) . ?
B1 C7 1.5483(19) . ?
O1 C1 1.4612(15) . ?
O2 C2 1.4600(15) . ?
C1 C3 1.5164(17) . ?
C1 C4 1.5229(18) . ?
C1 C2 1.5734(16) . ?
C2 C6 1.5169(17) . ?
C2 C5 1.5203(17) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C11 1.4347(17) . ?
C7 C8 1.4345(18) . ?
C8 C9 1.4194(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.4236(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.4229(18) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C16 1.4190(19) . ?
C12 C13 1.4219(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.422(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.417(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.424(2) . ?
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
C11 Fe C12 114.90(5) . . ?
C11 Fe C7 41.16(5) . . ?
C12 Fe C7 105.92(5) . . ?
C11 Fe C16 106.11(5) . . ?
C12 Fe C16 40.63(5) . . ?
C7 Fe C16 127.01(5) . . ?
C11 Fe C13 148.67(6) . . ?
C12 Fe C13 40.68(5) . . ?
C7 Fe C13 116.11(5) . . ?
C16 Fe C13 68.43(5) . . ?
C11 Fe C8 68.54(5) . . ?
C12 Fe C8 129.15(5) . . ?
C7 Fe C8 41.01(5) . . ?
C16 Fe C8 166.56(5) . . ?
C13 Fe C8 109.30(5) . . ?
C11 Fe C14 168.06(6) . . ?
C12 Fe C14 68.28(6) . . ?
C7 Fe C14 150.59(6) . . ?
C16 Fe C14 68.30(6) . . ?
C13 Fe C14 40.59(6) . . ?
C8 Fe C14 119.24(5) . . ?
C11 Fe C15 128.68(6) . . ?
C12 Fe C15 68.24(6) . . ?
C7 Fe C15 166.28(6) . . ?
C16 Fe C15 40.67(6) . . ?
C13 Fe C15 68.19(6) . . ?
C8 Fe C15 152.05(6) . . ?
C14 Fe C15 40.40(6) . . ?
C11 Fe C10 40.66(5) . . ?
C12 Fe C10 148.64(5) . . ?
C7 Fe C10 68.85(5) . . ?
C16 Fe C10 116.55(5) . . ?
C13 Fe C10 169.81(6) . . ?
C8 Fe C10 68.03(5) . . ?
C14 Fe C10 131.22(6) . . ?
C15 Fe C10 109.23(5) . . ?
C11 Fe C9 68.40(5) . . ?
C12 Fe C9 168.48(5) . . ?
C7 Fe C9 68.82(5) . . ?
C16 Fe C9 150.65(5) . . ?
C13 Fe C9 131.33(5) . . ?
C8 Fe C9 40.38(5) . . ?
C14 Fe C9 110.92(6) . . ?
C15 Fe C9 119.16(6) . . ?
C10 Fe C9 40.42(5) . . ?
O1 B1 O2 113.45(11) . . ?
O1 B1 C7 122.78(11) . . ?
O2 B1 C7 123.74(11) . . ?
B1 O1 C1 107.85(9) . . ?
B1 O2 C2 107.94(9) . . ?
O1 C1 C3 107.82(10) . . ?
O1 C1 C4 106.70(10) . . ?
C3 C1 C4 110.25(11) . . ?
O1 C1 C2 102.61(9) . . ?
C3 C1 C2 114.99(10) . . ?
C4 C1 C2 113.68(10) . . ?
O2 C2 C6 107.54(10) . . ?
O2 C2 C5 106.98(10) . . ?
C6 C2 C5 110.30(11) . . ?
O2 C2 C1 103.13(9) . . ?
C6 C2 C1 114.68(10) . . ?
C5 C2 C1 113.50(10) . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C11 C7 C8 106.68(11) . . ?
C11 C7 B1 127.24(11) . . ?
C8 C7 B1 125.16(11) . . ?
C11 C7 Fe 69.13(7) . . ?
C8 C7 Fe 69.72(7) . . ?
B1 C7 Fe 117.60(9) . . ?
C9 C8 C7 108.81(11) . . ?
C9 C8 Fe 70.24(7) . . ?
C7 C8 Fe 69.27(7) . . ?
C9 C8 H8 125.6 . . ?
C7 C8 H8 125.6 . . ?
Fe C8 H8 126.5 . . ?
C8 C9 C10 107.90(11) . . ?
C8 C9 Fe 69.38(7) . . ?
C10 C9 Fe 69.65(7) . . ?
C8 C9 H9 126.0 . . ?
C10 C9 H9 126.0 . . ?
Fe C9 H9 126.5 . . ?
C11 C10 C9 108.09(11) . . ?
C11 C10 Fe 68.86(7) . . ?
C9 C10 Fe 69.92(7) . . ?
C11 C10 H10 126.0 . . ?
C9 C10 H10 126.0 . . ?
Fe C10 H10 126.8 . . ?
C10 C11 C7 108.52(11) . . ?
C10 C11 Fe 70.48(7) . . ?
C7 C11 Fe 69.71(7) . . ?
C10 C11 H11 125.7 . . ?
C7 C11 H11 125.7 . . ?
Fe C11 H11 125.7 . . ?
C16 C12 C13 108.24(12) . . ?
C16 C12 Fe 69.79(8) . . ?
C13 C12 Fe 69.91(8) . . ?
C16 C12 H12 125.9 . . ?
C13 C12 H12 125.9 . . ?
Fe C12 H12 126.0 . . ?
C12 C13 C14 107.75(12) . . ?
C12 C13 Fe 69.41(7) . . ?
C14 C13 Fe 69.81(8) . . ?
C12 C13 H13 126.1 . . ?
C14 C13 H13 126.1 . . ?
Fe C13 H13 126.2 . . ?
C15 C14 C13 108.13(12) . . ?
C15 C14 Fe 69.84(8) . . ?
C13 C14 Fe 69.60(8) . . ?
C15 C14 H14 125.9 . . ?
C13 C14 H14 125.9 . . ?
Fe C14 H14 126.2 . . ?
C14 C15 C16 108.09(12) . . ?
C14 C15 Fe 69.76(8) . . ?
C16 C15 Fe 69.38(8) . . ?
C14 C15 H15 126.0 . . ?
C16 C15 H15 126.0 . . ?
Fe C15 H15 126.5 . . ?
C12 C16 C15 107.79(12) . . ?
C12 C16 Fe 69.58(7) . . ?
C15 C16 Fe 69.96(8) . . ?
C12 C16 H16 126.1 . . ?
C15 C16 H16 126.1 . . ?
Fe C16 H16 125.9 . . ?



