# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_n17_a22
_database_code_depnum_ccdc_archive 'CCDC 1574232'
_audit_update_record             
;
2017-09-13 deposited with the CCDC.
2018-01-17 downloaded from the CCDC.
;
_audit_creation_date             2017-09-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C27 H37 B Fe P2'
_chemical_formula_sum            'C27 H37 B Fe P2'
_chemical_formula_weight         490.17
_chemical_melting_point          ?
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'
P P 0.1023 0.0942 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   9.9177(4)
_cell_length_b                   11.5650(5)
_cell_length_c                   22.0296(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.9290(10)
_cell_angle_gamma                90.00
_cell_volume                     2520.82(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9146
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      30.35
_cell_measurement_theta_min      2.56
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0551 before and 0.0448 after correction. The Ratio of minimum to maximum transmission is 0.9014. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_special_details           
'The data collection nominally covered a full sphere of reciprocal space by a combination of 3 sets of ω scans each set at different φ and/or 2θ angles and each scan (10 s exposure) covering -0.300° degrees in ω. The crystal to detector distance was 5.05 cm.'
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            37814
_diffrn_reflns_theta_full        30.93
_diffrn_reflns_theta_max         30.93
_diffrn_reflns_theta_min         1.85
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.938
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           600.0
_diffrn_source_power             30.0
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                6511
_reflns_number_total             7498
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'SMART V5.631 (?, 2016)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         7498
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      0.925
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1217
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C25(H25A,H25B,
 H25C), C14(H14A,H14B,H14C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Fe1 Fe 0.023416(19) 0.778546(16) 0.291639(8) 0.01232(8) Uani 1 d . . .
P1 P 0.25229(3) 0.67011(3) 0.207252(16) 0.01189(9) Uani 1 d . . .
P2 P 0.00810(4) 0.83130(3) 0.142999(16) 0.01295(9) Uani 1 d . . .
C6 C -0.07830(14) 0.78752(12) 0.20911(6) 0.0135(3) Uani 1 d . . .
C19 C 0.24456(14) 0.73410(11) 0.07769(6) 0.0129(2) Uani 1 d . . .
C24 C 0.31971(14) 0.82840(12) 0.05734(6) 0.0146(3) Uani 1 d . . .
C22 C 0.40861(15) 0.71024(13) -0.02216(7) 0.0177(3) Uani 1 d . . .
C11 C 0.44206(14) 0.65831(12) 0.21114(6) 0.0146(3) Uani 1 d . . .
C2 C 0.20089(14) 0.86589(12) 0.28676(6) 0.0148(3) Uani 1 d . . .
C1 C 0.21639(14) 0.74384(12) 0.27638(6) 0.0126(2) Uani 1 d . . .
C23 C 0.39979(15) 0.81520(13) 0.00826(7) 0.0171(3) Uani 1 d . . .
C4 C 0.14035(16) 0.77022(13) 0.37290(7) 0.0180(3) Uani 1 d . . .
C3 C 0.15299(15) 0.88146(13) 0.34578(7) 0.0182(3) Uani 1 d . . .
C20 C 0.24833(14) 0.62890(12) 0.04521(6) 0.0146(3) Uani 1 d . . .
C15 C -0.12058(14) 0.80822(13) 0.07675(6) 0.0153(3) Uani 1 d . . .
B1 B 0.16937(16) 0.74467(13) 0.13841(7) 0.0127(3) Uani 1 d . . .
C10 C -0.09043(14) 0.67327(12) 0.23476(7) 0.0152(3) Uani 1 d . . .
C21 C 0.33025(15) 0.61839(13) -0.00347(6) 0.0172(3) Uani 1 d . . .
C7 C -0.13560(14) 0.86682(13) 0.25075(7) 0.0170(3) Uani 1 d . . .
C26 C 0.49742(17) 0.69630(16) -0.07440(7) 0.0244(3) Uani 1 d . . .
H26A H 0.4410 0.6834 -0.1121 0.037 Uiso 1 calc . . GR
H26B H 0.5576 0.6299 -0.0667 0.037 Uiso 1 calc . . GR
H26C H 0.5515 0.7665 -0.0784 0.037 Uiso 1 calc . . GR
C5 C 0.18019(15) 0.68584(13) 0.33069(7) 0.0159(3) Uani 1 d . . .
C17 C -0.05201(16) 0.81958(14) 0.01679(7) 0.0216(3) Uani 1 d . . .
H17A H 0.0022 0.8905 0.0175 0.032 Uiso 1 calc . . GR
H17B H -0.1211 0.8229 -0.0172 0.032 Uiso 1 calc . . GR
H17C H 0.0067 0.7526 0.0117 0.032 Uiso 1 calc . . GR
C8 C -0.18009(15) 0.80264(15) 0.30091(7) 0.0210(3) Uani 1 d . . .
C27 C 0.31611(17) 0.94549(13) 0.08804(7) 0.0204(3) Uani 1 d . . .
C9 C -0.15166(15) 0.68353(15) 0.29119(7) 0.0203(3) Uani 1 d . . .
C18 C -0.22656(16) 0.90450(14) 0.08043(7) 0.0225(3) Uani 1 d . . .
H18A H -0.2632 0.9032 0.1206 0.034 Uiso 1 calc . . GR
H18B H -0.2999 0.8920 0.0490 0.034 Uiso 1 calc . . GR
H18C H -0.1842 0.9797 0.0740 0.034 Uiso 1 calc . . GR
C16 C -0.19151(17) 0.69065(14) 0.07914(7) 0.0211(3) Uani 1 d . . .
C13 C 0.51169(18) 0.77493(14) 0.20472(9) 0.0234(3) Uani 1 d . . .
C25 C 0.16530(16) 0.52550(13) 0.06258(7) 0.0201(3) Uani 1 d . . .
H25A H 0.1474 0.5307 0.1057 0.030 Uiso 1 calc . . GR
H25B H 0.2154 0.4542 0.0555 0.030 Uiso 1 calc . . GR
H25C H 0.0794 0.5247 0.0378 0.030 Uiso 1 calc . . GR
C14 C 0.48354(15) 0.60605(13) 0.27393(7) 0.0192(3) Uani 1 d . . .
H14A H 0.4621 0.6608 0.3058 0.029 Uiso 1 calc . . GR
H14B H 0.5809 0.5904 0.2769 0.029 Uiso 1 calc . . GR
H14C H 0.4340 0.5338 0.2791 0.029 Uiso 1 calc . . GR
C12 C 0.48423(15) 0.57385(15) 0.16252(7) 0.0232(3) Uani 1 d . . .
H12A H 0.4338 0.5014 0.1655 0.035 Uiso 1 calc . . GR
H12B H 0.5813 0.5582 0.1688 0.035 Uiso 1 calc . . GR
H12C H 0.4646 0.6078 0.1221 0.035 Uiso 1 calc . . GR
H21 H 0.3406(19) 0.5451(17) -0.0228(8) 0.022(5) Uiso 1 d . . .
H23 H 0.4477(19) 0.8837(17) -0.0070(9) 0.024(5) Uiso 1 d . . .
H16A H -0.2633(19) 0.6814(16) 0.0415(9) 0.019(5) Uiso 1 d . . .
H13A H 0.613(2) 0.7677(18) 0.2118(10) 0.028(6) Uiso 1 d . . .
H16B H -0.127(2) 0.6286(19) 0.0749(9) 0.029(5) Uiso 1 d . . .
H3 H 0.1335(18) 0.9494(17) 0.3637(8) 0.016(4) Uiso 1 d . . .
H4 H 0.110(2) 0.7573(17) 0.4135(9) 0.019(5) Uiso 1 d . . .
H13B H 0.487(2) 0.8034(19) 0.1672(10) 0.028(5) Uiso 1 d . . .
H16C H -0.233(2) 0.6828(19) 0.1186(10) 0.031(6) Uiso 1 d . . .
H5 H 0.174(2) 0.600(2) 0.3344(9) 0.031(5) Uiso 1 d . . .
H2 H 0.214(2) 0.9264(19) 0.2558(9) 0.030(5) Uiso 1 d . . .
H27A H 0.3122(19) 0.9396(17) 0.1310(9) 0.023(5) Uiso 1 d . . .
H8 H -0.219(2) 0.8314(17) 0.3344(9) 0.024(5) Uiso 1 d . . .
H9 H -0.1709(19) 0.6210(17) 0.3193(9) 0.024(5) Uiso 1 d . . .
H27B H 0.397(2) 0.990(2) 0.0810(10) 0.037(6) Uiso 1 d . . .
H7 H -0.1445(18) 0.9454(16) 0.2471(8) 0.014(4) Uiso 1 d . . .
H10 H -0.0588(18) 0.6032(18) 0.2186(8) 0.021(5) Uiso 1 d . . .
H27C H 0.237(2) 0.9874(19) 0.0730(10) 0.036(6) Uiso 1 d . . .
H13C H 0.486(2) 0.8223(19) 0.2352(10) 0.029(5) Uiso 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
Fe1 C6 2.0205(14) . ?
Fe1 C2 2.0386(14) . ?
Fe1 C1 2.0063(14) . ?
Fe1 C4 2.0674(15) . ?
Fe1 C3 2.0689(14) . ?
Fe1 C10 2.0330(14) . ?
Fe1 C7 2.0362(14) . ?
Fe1 C5 2.0307(15) . ?
Fe1 C8 2.0614(15) . ?
Fe1 C9 2.0543(15) . ?
P1 C11 1.8830(14) . ?
P1 C1 1.8020(14) . ?
P1 B1 1.8838(16) . ?
P2 C6 1.8118(15) . ?
P2 C15 1.8906(14) . ?
P2 B1 1.8959(16) . ?
C6 C10 1.445(2) . ?
C6 C7 1.4412(19) . ?
C19 C24 1.4112(19) . ?
C19 C20 1.4132(19) . ?
C19 B1 1.580(2) . ?
C24 C23 1.3931(19) . ?
C24 C27 1.515(2) . ?
C22 C23 1.392(2) . ?
C22 C21 1.395(2) . ?
C22 C26 1.505(2) . ?
C11 C13 1.526(2) . ?
C11 C14 1.540(2) . ?
C11 C12 1.529(2) . ?
C2 C1 1.4398(19) . ?
C2 C3 1.426(2) . ?
C1 C5 1.4385(19) . ?
C4 C3 1.428(2) . ?
C4 C5 1.423(2) . ?
C20 C21 1.3944(19) . ?
C20 C25 1.516(2) . ?
C15 C17 1.532(2) . ?
C15 C18 1.537(2) . ?
C15 C16 1.533(2) . ?
C10 C9 1.425(2) . ?
C7 C8 1.426(2) . ?
C8 C9 1.425(2) . ?

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
C6 Fe1 C2 107.86(6) . . ?
C6 Fe1 C4 175.84(6) . . ?
C6 Fe1 C3 137.84(6) . . ?
C6 Fe1 C10 41.78(6) . . ?
C6 Fe1 C7 41.62(5) . . ?
C6 Fe1 C5 136.79(6) . . ?
C6 Fe1 C8 69.54(6) . . ?
C6 Fe1 C9 69.73(6) . . ?
C2 Fe1 C4 68.50(6) . . ?
C2 Fe1 C3 40.61(6) . . ?
C2 Fe1 C8 142.47(6) . . ?
C2 Fe1 C9 175.81(6) . . ?
C1 Fe1 C6 106.42(6) . . ?
C1 Fe1 C2 41.69(5) . . ?
C1 Fe1 C4 69.56(6) . . ?
C1 Fe1 C3 69.49(6) . . ?
C1 Fe1 C10 105.83(6) . . ?
C1 Fe1 C7 138.16(6) . . ?
C1 Fe1 C5 41.74(5) . . ?
C1 Fe1 C8 174.47(6) . . ?
C1 Fe1 C9 135.06(6) . . ?
C4 Fe1 C3 40.38(6) . . ?
C10 Fe1 C2 135.18(6) . . ?
C10 Fe1 C4 139.52(6) . . ?
C10 Fe1 C3 175.26(6) . . ?
C10 Fe1 C7 69.33(6) . . ?
C10 Fe1 C8 68.64(6) . . ?
C10 Fe1 C9 40.82(6) . . ?
C7 Fe1 C2 111.94(6) . . ?
C7 Fe1 C4 141.07(6) . . ?
C7 Fe1 C3 113.47(6) . . ?
C7 Fe1 C8 40.72(6) . . ?
C7 Fe1 C9 68.73(6) . . ?
C5 Fe1 C2 69.22(6) . . ?
C5 Fe1 C4 40.61(6) . . ?
C5 Fe1 C3 68.42(6) . . ?
C5 Fe1 C10 108.76(6) . . ?
C5 Fe1 C7 178.09(6) . . ?
C5 Fe1 C8 139.10(6) . . ?
C5 Fe1 C9 110.00(6) . . ?
C8 Fe1 C4 114.55(6) . . ?
C8 Fe1 C3 116.03(6) . . ?
C9 Fe1 C4 113.77(6) . . ?
C9 Fe1 C3 143.31(6) . . ?
C9 Fe1 C8 40.52(7) . . ?
C11 P1 B1 116.72(7) . . ?
C1 P1 C11 104.51(6) . . ?
C1 P1 B1 111.29(7) . . ?
C6 P2 C15 104.46(6) . . ?
C6 P2 B1 110.02(7) . . ?
C15 P2 B1 114.30(7) . . ?
P2 C6 Fe1 120.21(7) . . ?
C10 C6 Fe1 69.58(8) . . ?
C10 C6 P2 128.78(11) . . ?
C7 C6 Fe1 69.77(8) . . ?
C7 C6 P2 124.24(11) . . ?
C7 C6 C10 106.61(12) . . ?
C24 C19 C20 118.14(13) . . ?
C24 C19 B1 119.95(12) . . ?
C20 C19 B1 121.71(12) . . ?
C19 C24 C27 121.32(13) . . ?
C23 C24 C19 120.22(13) . . ?
C23 C24 C27 118.46(13) . . ?
C23 C22 C21 117.86(13) . . ?
C23 C22 C26 121.39(14) . . ?
C21 C22 C26 120.74(14) . . ?
C13 C11 P1 112.89(11) . . ?
C13 C11 C14 109.60(12) . . ?
C13 C11 C12 110.63(13) . . ?
C14 C11 P1 105.91(10) . . ?
C12 C11 P1 109.57(10) . . ?
C12 C11 C14 108.03(12) . . ?
C1 C2 Fe1 67.95(8) . . ?
C3 C2 Fe1 70.84(8) . . ?
C3 C2 C1 108.34(12) . . ?
P1 C1 Fe1 118.84(7) . . ?
C2 C1 Fe1 70.35(8) . . ?
C2 C1 P1 128.88(11) . . ?
C5 C1 Fe1 70.04(8) . . ?
C5 C1 P1 123.86(11) . . ?
C5 C1 C2 106.83(12) . . ?
C22 C23 C24 121.81(14) . . ?
C3 C4 Fe1 69.86(8) . . ?
C5 C4 Fe1 68.31(8) . . ?
C5 C4 C3 107.96(13) . . ?
C2 C3 Fe1 68.55(8) . . ?
C2 C3 C4 108.18(13) . . ?
C4 C3 Fe1 69.75(8) . . ?
C19 C20 C25 121.18(13) . . ?
C21 C20 C19 120.10(13) . . ?
C21 C20 C25 118.72(13) . . ?
C17 C15 P2 109.71(10) . . ?
C17 C15 C18 109.20(12) . . ?
C17 C15 C16 109.71(13) . . ?
C18 C15 P2 106.55(10) . . ?
C16 C15 P2 112.69(10) . . ?
C16 C15 C18 108.88(13) . . ?
P1 B1 P2 121.49(8) . . ?
C19 B1 P1 116.15(10) . . ?
C19 B1 P2 122.33(10) . . ?
C6 C10 Fe1 68.65(8) . . ?
C9 C10 Fe1 70.39(8) . . ?
C9 C10 C6 108.47(13) . . ?
C20 C21 C22 121.76(13) . . ?
C6 C7 Fe1 68.61(8) . . ?
C8 C7 Fe1 70.59(9) . . ?
C8 C7 C6 108.57(13) . . ?
C1 C5 Fe1 68.22(8) . . ?
C4 C5 Fe1 71.09(9) . . ?
C4 C5 C1 108.67(13) . . ?
C7 C8 Fe1 68.69(8) . . ?
C9 C8 Fe1 69.47(9) . . ?
C9 C8 C7 108.17(13) . . ?
C10 C9 Fe1 68.79(8) . . ?
C8 C9 Fe1 70.01(9) . . ?
C8 C9 C10 108.18(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
