# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_mo_molan101_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 B N4'
_chemical_formula_weight         324.19

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   9.1229(9)
_cell_length_b                   10.9815(11)
_cell_length_c                   16.3366(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1636.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9705
_cell_measurement_theta_min      5.805
_cell_measurement_theta_max      54.150

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9712
_exptl_absorpt_correction_T_max  0.9819
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42384
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0124
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         27.15
_reflns_number_total             3624
_reflns_number_gt                3515
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0431P)²+0.4723P] 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         3624
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0779
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.90631(14) 0.48239(12) 0.31263(8) 0.0129(2) Uani 1 1 d . . .
C7 C 0.83457(13) 0.59583(11) 0.36029(7) 0.0137(2) Uani 1 1 d . . .
C12 C 0.68193(14) 0.61000(12) 0.36408(7) 0.0167(2) Uani 1 1 d . . .
H12 H 0.6208 0.5490 0.3410 0.020 Uiso 1 1 calc R . .
C8 C 0.92035(14) 0.68875(11) 0.39496(7) 0.0161(2) Uani 1 1 d . . .
H8 H 1.0242 0.6826 0.3928 0.019 Uiso 1 1 calc R . .
C1 C 1.06820(13) 0.44199(11) 0.33994(7) 0.0134(2) Uani 1 1 d . . .
C3 C 1.24281(14) 0.40069(11) 0.44982(7) 0.0202(3) Uani 1 1 d . . .
H3 H 1.2654 0.4002 0.5066 0.024 Uiso 1 1 calc R . .
C2 C 1.10522(13) 0.43935(11) 0.42323(7) 0.0161(2) Uani 1 1 d . . .
H2 H 1.0348 0.4645 0.4625 0.019 Uiso 1 1 calc R . .
C10 C 0.70532(15) 0.80074(12) 0.43534(8) 0.0209(3) Uani 1 1 d . . .
H10 H 0.6617 0.8695 0.4609 0.025 Uiso 1 1 calc R . .
C9 C 0.85674(15) 0.78956(12) 0.43236(8) 0.0199(3) Uani 1 1 d . . .
H9 H 0.9170 0.8508 0.4559 0.024 Uiso 1 1 calc R . .
C5 C 1.31255(14) 0.36261(12) 0.31054(8) 0.0201(3) Uani 1 1 d . . .
H5 H 1.3830 0.3361 0.2716 0.024 Uiso 1 1 calc R . .
C6 C 1.17474(13) 0.40124(11) 0.28470(7) 0.0173(2) Uani 1 1 d . . .
H6 H 1.1524 0.3999 0.2279 0.021 Uiso 1 1 calc R . .
C11 C 0.61798(15) 0.71094(13) 0.40080(7) 0.0208(3) Uani 1 1 d . . .
H11 H 0.5143 0.7185 0.4023 0.025 Uiso 1 1 calc R . .
C4 C 1.34676(14) 0.36298(12) 0.39318(8) 0.0206(3) Uani 1 1 d . . .
H4 H 1.4410 0.3375 0.4110 0.025 Uiso 1 1 calc R . .
N2 N 0.80014(11) 0.37106(9) 0.30466(6) 0.0134(2) Uani 1 1 d . . .
N4 N 0.66725(11) 0.25029(9) 0.22479(6) 0.0166(2) Uani 1 1 d . . .
N1 N 0.90013(11) 0.51332(9) 0.21491(6) 0.0131(2) Uani 1 1 d . . .
N3 N 0.74046(11) 0.28718(9) 0.35620(6) 0.0148(2) Uani 1 1 d . . .
C17 C 0.81123(13) 0.43748(10) 0.17165(7) 0.0136(2) Uani 1 1 d . . .
C19 C 0.66194(13) 0.21684(11) 0.30516(7) 0.0152(2) Uani 1 1 d . . .
C18 C 0.75415(13) 0.34718(10) 0.22865(7) 0.0137(2) Uani 1 1 d . . .
C13 C 0.96702(13) 0.60682(11) 0.17772(7) 0.0158(2) Uani 1 1 d . . .
H13 H 1.0303 0.6583 0.2083 0.019 Uiso 1 1 calc R . .
C14 C 0.94501(14) 0.62907(11) 0.09544(7) 0.0176(2) Uani 1 1 d . . .
H14 H 0.9936 0.6950 0.0693 0.021 Uiso 1 1 calc R . .
C20 C 0.57474(15) 0.11041(12) 0.33462(8) 0.0210(3) Uani 1 1 d . . .
H20A H 0.5573 0.1184 0.3936 0.032 Uiso 1 1 calc R . .
H20B H 0.6291 0.0351 0.3239 0.032 Uiso 1 1 calc R . .
H20C H 0.4806 0.1079 0.3057 0.032 Uiso 1 1 calc R . .
C16 C 0.78401(13) 0.45561(11) 0.08915(7) 0.0172(2) Uani 1 1 d . . .
H16 H 0.7214 0.4024 0.0595 0.021 Uiso 1 1 calc R . .
C15 C 0.85133(14) 0.55429(12) 0.05111(7) 0.0184(3) Uani 1 1 d . . .
H15 H 0.8332 0.5705 -0.0051 0.022 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 N2 1.5652(16) . ?
B1 C1 1.6053(17) . ?
B1 C7 1.6081(17) . ?
B1 N1 1.6332(15) . ?
C7 C12 1.4026(17) . ?
C7 C8 1.4052(17) . ?
C12 C11 1.3889(18) . ?
C8 C9 1.3913(17) . ?
C1 C6 1.3997(17) . ?
C1 C2 1.4022(16) . ?
C3 C4 1.3881(18) . ?
C3 C2 1.3944(17) . ?
C10 C9 1.3877(19) . ?
C10 C11 1.3878(19) . ?
C5 C4 1.3856(18) . ?
C5 C6 1.3924(17) . ?
N2 C18 1.3367(15) . ?
N2 N3 1.3616(14) . ?
N4 C18 1.3284(15) . ?
N4 C19 1.3642(16) . ?
N1 C13 1.3400(15) . ?
N1 C17 1.3605(15) . ?
N3 C19 1.3435(16) . ?
C17 C16 1.3849(16) . ?
C17 C18 1.4566(16) . ?
C19 C20 1.4934(17) . ?
C13 C14 1.3809(17) . ?
C14 C15 1.3890(18) . ?
C16 C15 1.3919(18) . ?

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
N2 B1 C1 112.12(10) . . ?
N2 B1 C7 113.17(10) . . ?
C1 B1 C7 117.00(10) . . ?
N2 B1 N1 93.42(8) . . ?
C1 B1 N1 111.15(9) . . ?
C7 B1 N1 107.34(9) . . ?
C12 C7 C8 117.03(11) . . ?
C12 C7 B1 120.76(11) . . ?
C8 C7 B1 122.07(11) . . ?
C11 C12 C7 121.65(12) . . ?
C9 C8 C7 121.50(12) . . ?
C6 C1 C2 116.86(11) . . ?
C6 C1 B1 123.23(10) . . ?
C2 C1 B1 119.80(10) . . ?
C4 C3 C2 119.88(11) . . ?
C3 C2 C1 121.69(11) . . ?
C9 C10 C11 119.63(12) . . ?
C10 C9 C8 120.07(13) . . ?
C4 C5 C6 119.86(12) . . ?
C5 C6 C1 121.93(11) . . ?
C10 C11 C12 120.11(12) . . ?
C5 C4 C3 119.76(12) . . ?
C18 N2 N3 108.44(9) . . ?
C18 N2 B1 115.14(9) . . ?
N3 N2 B1 136.42(9) . . ?
C18 N4 C19 101.02(10) . . ?
C13 N1 C17 120.33(10) . . ?
C13 N1 B1 125.93(10) . . ?
C17 N1 B1 113.65(9) . . ?
C19 N3 N2 102.61(9) . . ?
N1 C17 C16 121.64(11) . . ?
N1 C17 C18 107.32(10) . . ?
C16 C17 C18 130.99(11) . . ?
N3 C19 N4 115.06(11) . . ?
N3 C19 C20 122.27(11) . . ?
N4 C19 C20 122.67(11) . . ?
N4 C18 N2 112.86(10) . . ?
N4 C18 C17 136.75(11) . . ?
N2 C18 C17 110.37(10) . . ?
N1 C13 C14 120.71(11) . . ?
C13 C14 C15 119.49(11) . . ?
C17 C16 C15 117.85(11) . . ?
C14 C15 C16 119.94(11) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.15
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.039
_database_code_depnum_ccdc_archive 'CCDC 1001413'
