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

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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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.
#
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#  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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#  data retrieval see:
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data_140407g

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H34 B N3'
_chemical_formula_weight         555.50

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '
_symmetry_space_group_name_Hall  'P 2ac 2ab'


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

_cell_length_a                   8.6210(9)
_cell_length_b                   18.3501(19)
_cell_length_c                   19.690(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3114.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    515
_cell_measurement_theta_min      2.5715
_cell_measurement_theta_max      26.4395

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1176
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15871
_diffrn_reflns_av_R_equivalents  0.1469
_diffrn_reflns_av_sigmaI/netI    0.2115
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         25.02
_reflns_number_total             5499
_reflns_number_gt                1840
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0272P)²+0.0000P] 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     constr
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(4)
_refine_ls_number_reflns         5499
_refine_ls_number_parameters     390
_refine_ls_number_restraints     1290
_refine_ls_R_factor_all          0.2034
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1190
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   0.752
_refine_ls_restrained_S_all      0.719
_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
N1 N 0.0829(4) 0.0776(2) 0.26509(17) 0.0524(9) Uani 1 1 d U . .
N2 N 0.2794(4) 0.0798(2) 0.35873(19) 0.0568(10) Uani 1 1 d U . .
N3 N -0.3923(6) -0.0843(3) 0.1366(2) 0.1018(15) Uani 1 1 d U . .
B1 B 0.0932(6) 0.0796(3) 0.3446(3) 0.0532(13) Uani 1 1 d U . .
C1 C 0.1768(5) 0.1227(3) 0.2279(2) 0.0558(12) Uani 1 1 d U . .
C2 C 0.3072(5) 0.1553(3) 0.2583(2) 0.0559(12) Uani 1 1 d U . .
C3 C 0.3673(5) 0.1279(3) 0.3210(2) 0.0571(12) Uani 1 1 d U . .
C4 C 0.5164(5) 0.1458(3) 0.3465(3) 0.0669(14) Uani 1 1 d U . .
H4 H 0.5756 0.1814 0.3250 0.080 Uiso 1 1 calc R . .
C5 C 0.5724(6) 0.1114(3) 0.4018(3) 0.0774(16) Uani 1 1 d U . .
H5 H 0.6704 0.1237 0.4179 0.093 Uiso 1 1 calc R . .
C6 C 0.4873(6) 0.0578(3) 0.4356(3) 0.0790(16) Uani 1 1 d U . .
H6 H 0.5288 0.0320 0.4720 0.095 Uiso 1 1 calc R . .
C7 C 0.3405(6) 0.0450(3) 0.4127(2) 0.0688(14) Uani 1 1 d U . .
H7 H 0.2800 0.0109 0.4353 0.083 Uiso 1 1 calc R . .
C8 C -0.0359(5) 0.0353(3) 0.2316(2) 0.0527(12) Uani 1 1 d U . .
C9 C -0.1899(5) 0.0438(2) 0.2512(2) 0.0636(12) Uani 1 1 d U . .
H9 H -0.2143 0.0762 0.2858 0.076 Uiso 1 1 calc R . .
C10 C -0.3077(5) 0.0047(3) 0.2200(3) 0.0702(14) Uani 1 1 d U . .
H10 H -0.4098 0.0118 0.2337 0.084 Uiso 1 1 calc R . .
C11 C -0.2763(6) -0.0437(3) 0.1698(3) 0.0740(15) Uani 1 1 d U . .
C12 C -0.1195(6) -0.0541(3) 0.1501(2) 0.0729(14) Uani 1 1 d U . .
H12 H -0.0944 -0.0880 0.1167 0.088 Uiso 1 1 calc R . .
C13 C -0.0041(5) -0.0134(3) 0.1811(2) 0.0636(13) Uani 1 1 d U . .
H13 H 0.0981 -0.0196 0.1671 0.076 Uiso 1 1 calc R . .
C14 C -0.5536(6) -0.0690(3) 0.1513(3) 0.124(2) Uani 1 1 d U . .
H14A H -0.5708 -0.0174 0.1501 0.186 Uiso 1 1 calc R . .
H14B H -0.5790 -0.0873 0.1957 0.186 Uiso 1 1 calc R . .
H14C H -0.6181 -0.0924 0.1180 0.186 Uiso 1 1 calc R . .
C15 C -0.3529(7) -0.1512(3) 0.1022(3) 0.117(2) Uani 1 1 d U . .
H15A H -0.2996 -0.1402 0.0607 0.175 Uiso 1 1 calc R . .
H15B H -0.4460 -0.1779 0.0923 0.175 Uiso 1 1 calc R . .
H15C H -0.2870 -0.1801 0.1309 0.175 Uiso 1 1 calc R . .
C16 C 0.1378(6) 0.1378(3) 0.1562(2) 0.0628(13) Uani 1 1 d U . .
C17 C -0.0084(6) 0.1622(3) 0.1375(3) 0.0698(14) Uani 1 1 d U . .
H17 H -0.0840 0.1687 0.1707 0.084 Uiso 1 1 calc R . .
C18 C -0.0439(7) 0.1769(3) 0.0703(3) 0.0915(17) Uani 1 1 d U . .
H18 H -0.1414 0.1949 0.0589 0.110 Uiso 1 1 calc R . .
C19 C 0.0630(9) 0.1652(3) 0.0213(3) 0.108(2) Uani 1 1 d U . .
H19 H 0.0379 0.1749 -0.0237 0.129 Uiso 1 1 calc R . .
C20 C 0.2096(8) 0.1391(3) 0.0371(3) 0.103(2) Uani 1 1 d U . .
H20 H 0.2821 0.1303 0.0030 0.124 Uiso 1 1 calc R . .
C21 C 0.2458(6) 0.1261(3) 0.1046(3) 0.0792(15) Uani 1 1 d U . .
H21 H 0.3443 0.1093 0.1158 0.095 Uiso 1 1 calc R . .
C22 C 0.3862(6) 0.2172(3) 0.2250(2) 0.0586(13) Uani 1 1 d U . .
C23 C 0.3114(6) 0.2825(3) 0.2188(2) 0.0678(14) Uani 1 1 d U . .
H23 H 0.2107 0.2865 0.2352 0.081 Uiso 1 1 calc R . .
C24 C 0.3789(7) 0.3423(3) 0.1894(2) 0.0813(16) Uani 1 1 d U . .
H24 H 0.3229 0.3853 0.1849 0.098 Uiso 1 1 calc R . .
C25 C 0.5309(7) 0.3385(3) 0.1665(2) 0.0840(16) Uani 1 1 d U . .
H25 H 0.5792 0.3793 0.1482 0.101 Uiso 1 1 calc R . .
C26 C 0.6091(6) 0.2733(3) 0.1712(3) 0.0846(17) Uani 1 1 d U . .
H26 H 0.7104 0.2697 0.1554 0.102 Uiso 1 1 calc R . .
C27 C 0.5374(6) 0.2136(3) 0.1992(2) 0.0763(15) Uani 1 1 d U . .
H27 H 0.5907 0.1695 0.2012 0.092 Uiso 1 1 calc R . .
C28 C 0.0202(5) 0.0091(3) 0.3804(2) 0.0569(12) Uani 1 1 d U . .
C29 C 0.0494(5) -0.0608(3) 0.3554(3) 0.0715(14) Uani 1 1 d U . .
H29 H 0.1094 -0.0657 0.3165 0.086 Uiso 1 1 calc R . .
C30 C -0.0082(6) -0.1234(3) 0.3867(3) 0.0820(16) Uani 1 1 d U . .
H30 H 0.0134 -0.1691 0.3687 0.098 Uiso 1 1 calc R . .
C31 C -0.0977(7) -0.1169(4) 0.4449(3) 0.0954(19) Uani 1 1 d U . .
H31 H -0.1376 -0.1583 0.4658 0.115 Uiso 1 1 calc R . .
C32 C -0.1270(6) -0.0498(4) 0.4713(3) 0.0925(17) Uani 1 1 d U . .
H32 H -0.1855 -0.0452 0.5108 0.111 Uiso 1 1 calc R . .
C33 C -0.0688(6) 0.0123(3) 0.4390(3) 0.0733(14) Uani 1 1 d U . .
H33 H -0.0908 0.0577 0.4576 0.088 Uiso 1 1 calc R . .
C34 C 0.0308(5) 0.1588(3) 0.3725(2) 0.0562(12) Uani 1 1 d U . .
C35 C -0.0670(5) 0.2044(3) 0.3353(2) 0.0627(13) Uani 1 1 d U . .
H35 H -0.0936 0.1911 0.2913 0.075 Uiso 1 1 calc R . .
C36 C -0.1256(6) 0.2682(3) 0.3612(3) 0.0791(16) Uani 1 1 d U . .
H36 H -0.1909 0.2967 0.3346 0.095 Uiso 1 1 calc R . .
C37 C -0.0894(7) 0.2903(3) 0.4253(3) 0.0884(17) Uani 1 1 d U . .
H37 H -0.1318 0.3330 0.4428 0.106 Uiso 1 1 calc R . .
C38 C 0.0096(7) 0.2494(3) 0.4636(3) 0.0880(18) Uani 1 1 d U . .
H38 H 0.0363 0.2643 0.5072 0.106 Uiso 1 1 calc R . .
C39 C 0.0707(6) 0.1847(3) 0.4369(3) 0.0743(14) Uani 1 1 d U . .
H39 H 0.1404 0.1581 0.4630 0.089 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
N1 C1 1.370(5) . ?
N1 C8 1.444(5) . ?
N1 B1 1.568(6) . ?
N2 C7 1.347(5) . ?
N2 C3 1.380(5) . ?
N2 B1 1.630(6) . ?
N3 C11 1.408(6) . ?
N3 C15 1.443(6) . ?
N3 C14 1.448(6) . ?
B1 C28 1.602(6) . ?
B1 C34 1.645(7) . ?
C1 C2 1.407(5) . ?
C1 C16 1.479(6) . ?
C2 C3 1.430(5) . ?
C2 C22 1.479(6) . ?
C3 C4 1.419(5) . ?
C4 C5 1.348(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.364(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.365(5) . ?
C8 C9 1.391(5) . ?
C9 C10 1.386(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.356(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.419(6) . ?
C12 C13 1.385(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.387(6) . ?
C16 C21 1.395(6) . ?
C17 C18 1.385(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.351(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.387(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.386(6) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.365(6) . ?
C22 C27 1.400(6) . ?
C23 C24 1.370(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.388(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.376(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.374(6) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C33 1.388(5) . ?
C28 C29 1.395(6) . ?
C29 C30 1.396(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.387(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.361(7) . ?
C31 H31 0.9300 . ?
C32 C33 1.398(6) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C34 C35 1.396(6) . ?
C34 C39 1.397(6) . ?
C35 C36 1.373(6) . ?
C35 H35 0.9300 . ?
C36 C37 1.362(6) . ?
C36 H36 0.9300 . ?
C37 C38 1.364(7) . ?
C37 H37 0.9300 . ?
C38 C39 1.401(6) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?

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
C1 N1 C8 120.0(4) . . ?
C1 N1 B1 119.0(4) . . ?
C8 N1 B1 120.6(4) . . ?
C7 N2 C3 120.9(4) . . ?
C7 N2 B1 121.3(4) . . ?
C3 N2 B1 116.8(4) . . ?
C11 N3 C15 120.1(5) . . ?
C11 N3 C14 119.2(5) . . ?
C15 N3 C14 119.0(5) . . ?
N1 B1 C28 113.5(4) . . ?
N1 B1 N2 103.1(4) . . ?
C28 B1 N2 108.3(4) . . ?
N1 B1 C34 109.6(4) . . ?
C28 B1 C34 116.0(4) . . ?
N2 B1 C34 105.2(4) . . ?
N1 C1 C2 120.1(4) . . ?
N1 C1 C16 119.3(4) . . ?
C2 C1 C16 120.5(4) . . ?
C1 C2 C3 120.5(4) . . ?
C1 C2 C22 120.4(4) . . ?
C3 C2 C22 119.1(4) . . ?
N2 C3 C4 117.1(5) . . ?
N2 C3 C2 119.4(4) . . ?
C4 C3 C2 123.5(5) . . ?
C5 C4 C3 120.1(5) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 121.8(5) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C7 C6 C5 116.8(5) . . ?
C7 C6 H6 121.6 . . ?
C5 C6 H6 121.6 . . ?
N2 C7 C6 122.9(5) . . ?
N2 C7 H7 118.6 . . ?
C6 C7 H7 118.6 . . ?
C13 C8 C9 117.8(5) . . ?
C13 C8 N1 122.9(4) . . ?
C9 C8 N1 119.4(4) . . ?
C10 C9 C8 121.3(4) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C9 121.0(5) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 N3 122.9(5) . . ?
C10 C11 C12 118.5(5) . . ?
N3 C11 C12 118.6(5) . . ?
C13 C12 C11 119.4(5) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C8 C13 C12 122.0(4) . . ?
C8 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 117.6(5) . . ?
C17 C16 C1 121.4(5) . . ?
C21 C16 C1 121.0(5) . . ?
C18 C17 C16 121.1(5) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C19 C18 C17 120.0(6) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 121.2(6) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C21 C20 C19 118.6(6) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C20 C21 C16 121.4(5) . . ?
C20 C21 H21 119.3 . . ?
C16 C21 H21 119.3 . . ?
C23 C22 C27 116.7(5) . . ?
C23 C22 C2 119.7(5) . . ?
C27 C22 C2 123.5(5) . . ?
C22 C23 C24 122.7(5) . . ?
C22 C23 H23 118.7 . . ?
C24 C23 H23 118.7 . . ?
C23 C24 C25 119.9(6) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C26 C25 C24 119.0(6) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C27 C26 C25 120.0(5) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C22 121.7(5) . . ?
C26 C27 H27 119.2 . . ?
C22 C27 H27 119.2 . . ?
C33 C28 C29 115.6(5) . . ?
C33 C28 B1 123.3(5) . . ?
C29 C28 B1 121.0(5) . . ?
C28 C29 C30 122.4(5) . . ?
C28 C29 H29 118.8 . . ?
C30 C29 H29 118.8 . . ?
C31 C30 C29 119.5(6) . . ?
C31 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
C32 C31 C30 119.7(6) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C31 C32 C33 119.9(6) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C28 C33 C32 122.8(5) . . ?
C28 C33 H33 118.6 . . ?
C32 C33 H33 118.6 . . ?
C35 C34 C39 114.9(5) . . ?
C35 C34 B1 123.5(4) . . ?
C39 C34 B1 121.6(5) . . ?
C36 C35 C34 122.6(5) . . ?
C36 C35 H35 118.7 . . ?
C34 C35 H35 118.7 . . ?
C37 C36 C35 120.9(6) . . ?
C37 C36 H36 119.6 . . ?
C35 C36 H36 119.6 . . ?
C36 C37 C38 119.4(6) . . ?
C36 C37 H37 120.3 . . ?
C38 C37 H37 120.3 . . ?
C37 C38 C39 119.6(6) . . ?
C37 C38 H38 120.2 . . ?
C39 C38 H38 120.2 . . ?
C34 C39 C38 122.5(5) . . ?
C34 C39 H39 118.8 . . ?
C38 C39 H39 118.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 B1 C28 -161.9(4) . . . . ?
C8 N1 B1 C28 25.4(6) . . . . ?
C1 N1 B1 N2 -45.0(5) . . . . ?
C8 N1 B1 N2 142.2(4) . . . . ?
C1 N1 B1 C34 66.7(5) . . . . ?
C8 N1 B1 C34 -106.1(4) . . . . ?
C7 N2 B1 N1 -144.9(4) . . . . ?
C3 N2 B1 N1 47.0(5) . . . . ?
C7 N2 B1 C28 -24.4(6) . . . . ?
C3 N2 B1 C28 167.5(4) . . . . ?
C7 N2 B1 C34 100.2(5) . . . . ?
C3 N2 B1 C34 -67.8(5) . . . . ?
C8 N1 C1 C2 -170.3(4) . . . . ?
B1 N1 C1 C2 16.9(6) . . . . ?
C8 N1 C1 C16 10.9(6) . . . . ?
B1 N1 C1 C16 -161.9(4) . . . . ?
N1 C1 C2 C3 16.7(6) . . . . ?
C16 C1 C2 C3 -164.6(4) . . . . ?
N1 C1 C2 C22 -164.8(4) . . . . ?
C16 C1 C2 C22 13.9(7) . . . . ?
C7 N2 C3 C4 -7.7(6) . . . . ?
B1 N2 C3 C4 160.4(4) . . . . ?
C7 N2 C3 C2 170.5(4) . . . . ?
B1 N2 C3 C2 -21.4(6) . . . . ?
C1 C2 C3 N2 -13.4(6) . . . . ?
C22 C2 C3 N2 168.1(4) . . . . ?
C1 C2 C3 C4 164.6(4) . . . . ?
C22 C2 C3 C4 -13.9(7) . . . . ?
N2 C3 C4 C5 5.9(7) . . . . ?
C2 C3 C4 C5 -172.2(5) . . . . ?
C3 C4 C5 C6 0.0(7) . . . . ?
C4 C5 C6 C7 -4.1(8) . . . . ?
C3 N2 C7 C6 3.7(7) . . . . ?
B1 N2 C7 C6 -163.9(5) . . . . ?
C5 C6 C7 N2 2.3(8) . . . . ?
C1 N1 C8 C13 58.4(6) . . . . ?
B1 N1 C8 C13 -128.9(5) . . . . ?
C1 N1 C8 C9 -122.0(4) . . . . ?
B1 N1 C8 C9 50.7(6) . . . . ?
C13 C8 C9 C10 -0.8(7) . . . . ?
N1 C8 C9 C10 179.5(4) . . . . ?
C8 C9 C10 C11 0.8(8) . . . . ?
C9 C10 C11 N3 -179.8(5) . . . . ?
C9 C10 C11 C12 0.6(8) . . . . ?
C15 N3 C11 C10 -158.1(5) . . . . ?
C14 N3 C11 C10 6.5(8) . . . . ?
C15 N3 C11 C12 21.5(8) . . . . ?
C14 N3 C11 C12 -173.9(5) . . . . ?
C10 C11 C12 C13 -1.8(8) . . . . ?
N3 C11 C12 C13 178.6(5) . . . . ?
C9 C8 C13 C12 -0.5(7) . . . . ?
N1 C8 C13 C12 179.2(4) . . . . ?
C11 C12 C13 C8 1.8(7) . . . . ?
N1 C1 C16 C17 52.3(6) . . . . ?
C2 C1 C16 C17 -126.5(5) . . . . ?
N1 C1 C16 C21 -125.9(5) . . . . ?
C2 C1 C16 C21 55.3(6) . . . . ?
C21 C16 C17 C18 -2.4(7) . . . . ?
C1 C16 C17 C18 179.4(4) . . . . ?
C16 C17 C18 C19 2.3(8) . . . . ?
C17 C18 C19 C20 -0.5(9) . . . . ?
C18 C19 C20 C21 -1.1(10) . . . . ?
C19 C20 C21 C16 1.0(9) . . . . ?
C17 C16 C21 C20 0.7(7) . . . . ?
C1 C16 C21 C20 178.9(5) . . . . ?
C1 C2 C22 C23 67.0(6) . . . . ?
C3 C2 C22 C23 -114.5(5) . . . . ?
C1 C2 C22 C27 -113.8(5) . . . . ?
C3 C2 C22 C27 64.7(6) . . . . ?
C27 C22 C23 C24 -0.3(7) . . . . ?
C2 C22 C23 C24 179.0(4) . . . . ?
C22 C23 C24 C25 -2.1(8) . . . . ?
C23 C24 C25 C26 2.7(8) . . . . ?
C24 C25 C26 C27 -1.0(8) . . . . ?
C25 C26 C27 C22 -1.5(8) . . . . ?
C23 C22 C27 C26 2.1(7) . . . . ?
C2 C22 C27 C26 -177.1(5) . . . . ?
N1 B1 C28 C33 -139.3(4) . . . . ?
N2 B1 C28 C33 106.9(5) . . . . ?
C34 B1 C28 C33 -11.1(6) . . . . ?
N1 B1 C28 C29 43.7(6) . . . . ?
N2 B1 C28 C29 -70.1(5) . . . . ?
C34 B1 C28 C29 171.9(4) . . . . ?
C33 C28 C29 C30 0.6(7) . . . . ?
B1 C28 C29 C30 177.8(4) . . . . ?
C28 C29 C30 C31 -0.1(7) . . . . ?
C29 C30 C31 C32 -0.8(8) . . . . ?
C30 C31 C32 C33 1.1(9) . . . . ?
C29 C28 C33 C32 -0.3(7) . . . . ?
B1 C28 C33 C32 -177.5(5) . . . . ?
C31 C32 C33 C28 -0.5(8) . . . . ?
N1 B1 C34 C35 21.8(6) . . . . ?
C28 B1 C34 C35 -108.3(5) . . . . ?
N2 B1 C34 C35 132.0(4) . . . . ?
N1 B1 C34 C39 -159.6(4) . . . . ?
C28 B1 C34 C39 70.4(6) . . . . ?
N2 B1 C34 C39 -49.3(6) . . . . ?
C39 C34 C35 C36 -3.0(7) . . . . ?
B1 C34 C35 C36 175.8(4) . . . . ?
C34 C35 C36 C37 0.4(8) . . . . ?
C35 C36 C37 C38 1.7(8) . . . . ?
C36 C37 C38 C39 -1.0(8) . . . . ?
C35 C34 C39 C38 3.7(7) . . . . ?
B1 C34 C39 C38 -175.1(4) . . . . ?
C37 C38 C39 C34 -1.9(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.033
_database_code_depnum_ccdc_archive 'CCDC 1013247'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_exp_4178

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H19 B F2 N2'
_chemical_formula_weight         396.23

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   10.9427(7)
_cell_length_b                   12.7077(7)
_cell_length_c                   14.9474(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2078.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1800
_cell_measurement_theta_min      3.2920
_cell_measurement_theta_max      20.2650

_exptl_crystal_description       yellow
_exptl_crystal_colour            block
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9889
_exptl_absorpt_correction_T_max  0.9906
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_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            14308
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_sigmaI/netI    0.0765
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3651
_reflns_number_gt                2412
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0328P)²+0.0000P] 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   0.6(11)
_refine_ls_number_reflns         3651
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.8388(3) 0.6364(2) 0.1994(3) 0.0352(9) Uani 1 1 d . . .
F1 F 0.82248(17) 0.58138(12) 0.11981(13) 0.0512(5) Uani 1 1 d . . .
F2 F 0.95953(15) 0.67273(12) 0.20235(14) 0.0532(5) Uani 1 1 d . . .
N1 N 0.7474(2) 0.72494(15) 0.20860(17) 0.0329(6) Uani 1 1 d . . .
N2 N 0.8220(2) 0.55881(17) 0.27898(18) 0.0365(7) Uani 1 1 d . . .
C1 C 0.7127(3) 0.77961(19) 0.1285(2) 0.0354(7) Uani 1 1 d . . .
C2 C 0.8025(3) 0.8163(2) 0.0722(2) 0.0520(9) Uani 1 1 d . . .
H2 H 0.8841 0.8070 0.0876 0.062 Uiso 1 1 calc R . .
C3 C 0.7731(4) 0.8668(3) -0.0071(3) 0.0713(12) Uani 1 1 d . . .
H3 H 0.8347 0.8915 -0.0445 0.086 Uiso 1 1 calc R . .
C4 C 0.6528(5) 0.8804(3) -0.0302(3) 0.0725(13) Uani 1 1 d . . .
H4 H 0.6329 0.9131 -0.0839 0.087 Uiso 1 1 calc R . .
C5 C 0.5617(4) 0.8458(3) 0.0257(3) 0.0619(11) Uani 1 1 d . . .
H5 H 0.4803 0.8572 0.0108 0.074 Uiso 1 1 calc R . .
C6 C 0.5912(3) 0.7938(2) 0.1045(2) 0.0471(9) Uani 1 1 d . . .
H6 H 0.5294 0.7683 0.1413 0.056 Uiso 1 1 calc R . .
C7 C 0.7048(3) 0.75373(19) 0.2906(2) 0.0316(7) Uani 1 1 d . . .
C8 C 0.6314(3) 0.8520(2) 0.2975(2) 0.0402(8) Uani 1 1 d . . .
C9 C 0.6797(3) 0.9483(2) 0.2727(2) 0.0515(10) Uani 1 1 d . . .
H9 H 0.7600 0.9530 0.2527 0.062 Uiso 1 1 calc R . .
C10 C 0.6072(5) 1.0381(3) 0.2780(3) 0.0726(13) Uani 1 1 d . . .
H10 H 0.6395 1.1036 0.2633 0.087 Uiso 1 1 calc R . .
C11 C 0.4879(5) 1.0297(3) 0.3051(3) 0.0825(16) Uani 1 1 d . . .
H11 H 0.4390 1.0895 0.3065 0.099 Uiso 1 1 calc R . .
C12 C 0.4397(4) 0.9353(3) 0.3301(3) 0.0755(13) Uani 1 1 d . . .
H12 H 0.3590 0.9307 0.3492 0.091 Uiso 1 1 calc R . .
C13 C 0.5122(3) 0.8465(3) 0.3264(3) 0.0550(10) Uani 1 1 d . . .
H13 H 0.4800 0.7820 0.3439 0.066 Uiso 1 1 calc R . .
C14 C 0.7250(3) 0.6938(2) 0.3659(2) 0.0354(8) Uani 1 1 d . . .
C15 C 0.6931(3) 0.7364(2) 0.4562(2) 0.0404(8) Uani 1 1 d . . .
C16 C 0.7554(3) 0.8228(2) 0.4893(2) 0.0530(10) Uani 1 1 d . . .
H16 H 0.8181 0.8521 0.4555 0.064 Uiso 1 1 calc R . .
C17 C 0.7271(4) 0.8665(3) 0.5708(3) 0.0713(12) Uani 1 1 d . . .
H17 H 0.7708 0.9244 0.5914 0.086 Uiso 1 1 calc R . .
C18 C 0.6346(4) 0.8250(3) 0.6220(3) 0.0691(11) Uani 1 1 d . . .
H18 H 0.6156 0.8543 0.6773 0.083 Uiso 1 1 calc R . .
C19 C 0.5708(4) 0.7403(3) 0.5907(3) 0.0619(10) Uani 1 1 d . . .
H19 H 0.5077 0.7123 0.6249 0.074 Uiso 1 1 calc R . .
C20 C 0.5990(3) 0.6957(2) 0.5087(3) 0.0511(9) Uani 1 1 d . . .
H20 H 0.5546 0.6380 0.4885 0.061 Uiso 1 1 calc R . .
C21 C 0.7782(3) 0.5905(2) 0.3592(2) 0.0375(8) Uani 1 1 d . . .
C22 C 0.7834(3) 0.5199(2) 0.4317(2) 0.0550(10) Uani 1 1 d . . .
H22 H 0.7578 0.5414 0.4881 0.066 Uiso 1 1 calc R . .
C23 C 0.8260(4) 0.4200(3) 0.4193(3) 0.0695(12) Uani 1 1 d . . .
H23 H 0.8276 0.3732 0.4672 0.083 Uiso 1 1 calc R . .
C24 C 0.8664(4) 0.3883(3) 0.3366(3) 0.0668(12) Uani 1 1 d . . .
H24 H 0.8941 0.3200 0.3274 0.080 Uiso 1 1 calc R . .
C25 C 0.8648(3) 0.4589(2) 0.2690(2) 0.0524(10) Uani 1 1 d . . .
H25 H 0.8942 0.4384 0.2133 0.063 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 1.392(4) . ?
B1 F2 1.400(4) . ?
B1 N1 1.512(4) . ?
B1 N2 1.555(4) . ?
N1 C7 1.361(4) . ?
N1 C1 1.435(4) . ?
N2 C21 1.353(4) . ?
N2 C25 1.361(3) . ?
C1 C2 1.375(4) . ?
C1 C6 1.389(4) . ?
C2 C3 1.386(5) . ?
C3 C4 1.372(5) . ?
C4 C5 1.373(5) . ?
C5 C6 1.388(5) . ?
C7 C14 1.377(4) . ?
C7 C8 1.489(4) . ?
C8 C13 1.375(4) . ?
C8 C9 1.384(4) . ?
C9 C10 1.392(5) . ?
C10 C11 1.371(5) . ?
C11 C12 1.363(5) . ?
C12 C13 1.381(5) . ?
C14 C21 1.439(4) . ?
C14 C15 1.496(4) . ?
C15 C16 1.384(4) . ?
C15 C20 1.394(4) . ?
C16 C17 1.374(5) . ?
C17 C18 1.374(5) . ?
C18 C19 1.365(5) . ?
C19 C20 1.386(5) . ?
C21 C22 1.408(4) . ?
C22 C23 1.364(4) . ?
C23 C24 1.374(5) . ?
C24 C25 1.351(5) . ?

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 108.3(3) . . ?
F1 B1 N1 111.5(3) . . ?
F2 B1 N1 112.1(2) . . ?
F1 B1 N2 108.7(2) . . ?
F2 B1 N2 107.3(3) . . ?
N1 B1 N2 108.9(3) . . ?
C7 N1 C1 122.0(2) . . ?
C7 N1 B1 120.5(2) . . ?
C1 N1 B1 117.4(3) . . ?
C21 N2 C25 119.8(3) . . ?
C21 N2 B1 122.1(2) . . ?
C25 N2 B1 117.8(3) . . ?
C2 C1 C6 118.8(3) . . ?
C2 C1 N1 119.0(3) . . ?
C6 C1 N1 122.1(3) . . ?
C1 C2 C3 121.0(4) . . ?
C4 C3 C2 119.7(4) . . ?
C3 C4 C5 120.2(4) . . ?
C4 C5 C6 120.0(4) . . ?
C1 C6 C5 120.2(3) . . ?
N1 C7 C14 122.2(2) . . ?
N1 C7 C8 118.2(3) . . ?
C14 C7 C8 119.6(3) . . ?
C13 C8 C9 119.4(3) . . ?
C13 C8 C7 119.4(3) . . ?
C9 C8 C7 121.1(3) . . ?
C8 C9 C10 119.5(4) . . ?
C11 C10 C9 119.7(4) . . ?
C12 C11 C10 121.3(4) . . ?
C11 C12 C13 119.1(4) . . ?
C8 C13 C12 121.1(4) . . ?
C7 C14 C21 120.9(3) . . ?
C7 C14 C15 120.0(2) . . ?
C21 C14 C15 119.1(3) . . ?
C16 C15 C20 117.2(3) . . ?
C16 C15 C14 119.6(3) . . ?
C20 C15 C14 123.1(3) . . ?
C17 C16 C15 121.8(3) . . ?
C16 C17 C18 120.3(4) . . ?
C19 C18 C17 119.3(4) . . ?
C18 C19 C20 120.8(4) . . ?
C19 C20 C15 120.7(3) . . ?
N2 C21 C22 118.5(3) . . ?
N2 C21 C14 118.4(3) . . ?
C22 C21 C14 123.0(3) . . ?
C23 C22 C21 120.2(4) . . ?
C22 C23 C24 120.3(4) . . ?
C25 C24 C23 118.3(3) . . ?
C24 C25 N2 122.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 1013248'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_exp_4179

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C54 H48 B2 F4 N6'
_chemical_formula_weight         878.60

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'
F F 0.0171 0.0103 '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'

_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                   12.2723(9)
_cell_length_b                   14.7050(16)
_cell_length_c                   14.7883(16)
_cell_angle_alpha                69.664(10)
_cell_angle_beta                 67.961(8)
_cell_angle_gamma                82.665(7)
_cell_volume                     2319.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2202
_cell_measurement_theta_min      2.8210
_cell_measurement_theta_max      21.4770

_exptl_crystal_description       yellow
_exptl_crystal_colour            block
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9932
_exptl_absorpt_correction_T_max  0.9941
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_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            15483
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_sigmaI/netI    0.0958
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         25.02
_reflns_number_total             8180
_reflns_number_gt                4187
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0777P)²+0.6088P] 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     SHELXL
_refine_ls_extinction_coef       0.0075(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8180
_refine_ls_number_parameters     600
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1462
_refine_ls_R_factor_gt           0.0752
_refine_ls_wR_factor_ref         0.2352
_refine_ls_wR_factor_gt          0.1889
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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 0.4450(4) 1.0614(3) 0.2995(4) 0.0456(11) Uani 1 1 d . . .
B2 B 0.6661(5) 0.5699(4) 1.1619(4) 0.0559(13) Uani 1 1 d . . .
F1 F 0.3925(2) 1.13768(16) 0.24340(18) 0.0652(7) Uani 1 1 d . . .
F2 F 0.5364(2) 1.10089(17) 0.30712(18) 0.0655(7) Uani 1 1 d . . .
F3 F 0.6028(3) 0.64729(19) 1.1811(2) 0.1239(15) Uani 1 1 d . . .
F4 F 0.7429(3) 0.5446(3) 1.2153(2) 0.1205(14) Uani 1 1 d . . .
N1 N 0.4973(3) 0.9904(2) 0.2383(3) 0.0582(10) Uani 1 1 d . . .
N2 N 0.3580(3) 1.0097(2) 0.4050(2) 0.0475(8) Uani 1 1 d . . .
N3 N 0.1592(4) 1.2686(3) 0.6300(4) 0.0956(15) Uani 1 1 d . . .
N4 N 0.5817(3) 0.4824(2) 1.2061(2) 0.0460(8) Uani 1 1 d . . .
N5 N 0.7313(3) 0.5889(2) 1.0476(2) 0.0440(8) Uani 1 1 d . . .
N6 N 0.9137(4) 0.9699(3) 0.8422(3) 0.0828(13) Uani 1 1 d . . .
C1 C 0.5825(5) 1.0262(4) 0.1450(4) 0.098(2) Uani 1 1 d . . .
H1 H 0.6034 1.0913 0.1215 0.118 Uiso 1 1 calc R . .
C2 C 0.6384(6) 0.9714(4) 0.0847(4) 0.122(3) Uani 1 1 d . . .
H2 H 0.6969 0.9980 0.0209 0.146 Uiso 1 1 calc R . .
C3 C 0.6071(5) 0.8748(4) 0.1193(4) 0.094(2) Uani 1 1 d . . .
H3 H 0.6446 0.8356 0.0789 0.113 Uiso 1 1 calc R . .
C4 C 0.5218(4) 0.8377(3) 0.2121(3) 0.0649(13) Uani 1 1 d . . .
H4 H 0.5014 0.7726 0.2353 0.078 Uiso 1 1 calc R . .
C5 C 0.4638(3) 0.8953(3) 0.2738(3) 0.0479(10) Uani 1 1 d . . .
C6 C 0.3749(3) 0.8591(3) 0.3734(3) 0.0437(10) Uani 1 1 d . . .
C7 C 0.3380(3) 0.7549(3) 0.4091(3) 0.0451(10) Uani 1 1 d . . .
C8 C 0.2740(4) 0.7265(3) 0.3655(4) 0.0614(12) Uani 1 1 d . . .
H8 H 0.2535 0.7724 0.3127 0.074 Uiso 1 1 calc R . .
C9 C 0.2383(4) 0.6309(3) 0.3977(5) 0.0760(15) Uani 1 1 d . . .
H9 H 0.1974 0.6127 0.3650 0.091 Uiso 1 1 calc R . .
C10 C 0.2640(5) 0.5642(3) 0.4776(4) 0.0776(17) Uani 1 1 d . . .
H10 H 0.2384 0.5004 0.5015 0.093 Uiso 1 1 calc R . .
C11 C 0.3264(5) 0.5908(3) 0.5219(4) 0.0848(17) Uani 1 1 d . . .
H11 H 0.3442 0.5449 0.5762 0.102 Uiso 1 1 calc R . .
C12 C 0.3647(4) 0.6855(3) 0.4881(4) 0.0695(14) Uani 1 1 d . . .
H12 H 0.4089 0.7022 0.5191 0.083 Uiso 1 1 calc R . .
C13 C 0.3269(3) 0.9153(3) 0.4354(3) 0.0412(9) Uani 1 1 d . . .
C14 C 0.2387(3) 0.8725(3) 0.5411(3) 0.0437(10) Uani 1 1 d . . .
C15 C 0.2735(4) 0.8437(3) 0.6245(3) 0.0648(13) Uani 1 1 d . . .
H15 H 0.3495 0.8571 0.6158 0.078 Uiso 1 1 calc R . .
C16 C 0.1966(5) 0.7950(4) 0.7214(4) 0.0799(16) Uani 1 1 d . . .
H16 H 0.2208 0.7761 0.7779 0.096 Uiso 1 1 calc R . .
C17 C 0.0850(5) 0.7743(3) 0.7348(4) 0.0764(15) Uani 1 1 d . . .
H17 H 0.0336 0.7403 0.7998 0.092 Uiso 1 1 calc R . .
C18 C 0.0498(4) 0.8040(4) 0.6522(4) 0.0732(14) Uani 1 1 d . . .
H18 H -0.0265 0.7910 0.6613 0.088 Uiso 1 1 calc R . .
C19 C 0.1259(4) 0.8530(3) 0.5553(3) 0.0595(12) Uani 1 1 d . . .
H19 H 0.1008 0.8729 0.4994 0.071 Uiso 1 1 calc R . .
C20 C 0.3011(4) 1.0695(3) 0.4698(3) 0.0465(10) Uani 1 1 d . . .
C21 C 0.2008(4) 1.1197(3) 0.4642(3) 0.0537(11) Uani 1 1 d . . .
H21 H 0.1642 1.1102 0.4234 0.064 Uiso 1 1 calc R . .
C22 C 0.1529(4) 1.1841(3) 0.5178(3) 0.0574(12) Uani 1 1 d . . .
H22 H 0.0844 1.2169 0.5126 0.069 Uiso 1 1 calc R . .
C23 C 0.2043(4) 1.2009(3) 0.5786(3) 0.0561(11) Uani 1 1 d . . .
C24 C 0.3059(4) 1.1487(3) 0.5848(3) 0.0655(13) Uani 1 1 d . . .
H24 H 0.3420 1.1570 0.6266 0.079 Uiso 1 1 calc R . .
C25 C 0.3540(4) 1.0853(3) 0.5303(3) 0.0589(12) Uani 1 1 d . . .
H25 H 0.4231 1.0528 0.5343 0.071 Uiso 1 1 calc R . .
C26 C 0.0497(5) 1.3141(4) 0.6309(4) 0.0904(17) Uani 1 1 d . . .
H26A H 0.0543 1.3494 0.5614 0.136 Uiso 1 1 calc R . .
H26B H 0.0316 1.3581 0.6697 0.136 Uiso 1 1 calc R . .
H26C H -0.0109 1.2657 0.6622 0.136 Uiso 1 1 calc R . .
C27 C 0.2092(6) 1.2809(5) 0.6971(5) 0.110(2) Uani 1 1 d . . .
H27A H 0.2028 1.2214 0.7530 0.164 Uiso 1 1 calc R . .
H27B H 0.1682 1.3313 0.7241 0.164 Uiso 1 1 calc R . .
H27C H 0.2906 1.2984 0.6597 0.164 Uiso 1 1 calc R . .
C28 C 0.4998(4) 0.4685(3) 1.3015(3) 0.0580(12) Uani 1 1 d . . .
H28 H 0.4904 0.5159 1.3321 0.070 Uiso 1 1 calc R . .
C29 C 0.4310(4) 0.3887(3) 1.3540(3) 0.0670(13) Uani 1 1 d . . .
H29 H 0.3755 0.3811 1.4195 0.080 Uiso 1 1 calc R . .
C30 C 0.4446(4) 0.3184(3) 1.3084(3) 0.0642(13) Uani 1 1 d . . .
H30 H 0.3998 0.2619 1.3437 0.077 Uiso 1 1 calc R . .
C31 C 0.5246(4) 0.3326(3) 1.2109(3) 0.0549(11) Uani 1 1 d . . .
H31 H 0.5332 0.2856 1.1798 0.066 Uiso 1 1 calc R . .
C32 C 0.5937(3) 0.4165(3) 1.1571(3) 0.0459(10) Uani 1 1 d . . .
C33 C 0.6761(3) 0.4359(3) 1.0537(3) 0.0455(10) Uani 1 1 d . . .
C34 C 0.6921(4) 0.3613(3) 1.0029(3) 0.0509(11) Uani 1 1 d . . .
C35 C 0.7912(4) 0.3044(3) 0.9885(3) 0.0691(14) Uani 1 1 d . . .
H35 H 0.8494 0.3122 1.0113 0.083 Uiso 1 1 calc R . .
C36 C 0.8055(6) 0.2361(4) 0.9407(4) 0.0920(19) Uani 1 1 d . . .
H36 H 0.8734 0.1987 0.9315 0.110 Uiso 1 1 calc R . .
C37 C 0.7225(8) 0.2223(4) 0.9066(4) 0.102(2) Uani 1 1 d . . .
H37 H 0.7331 0.1760 0.8744 0.123 Uiso 1 1 calc R . .
C38 C 0.6240(7) 0.2773(5) 0.9203(5) 0.105(2) Uani 1 1 d . . .
H38 H 0.5664 0.2687 0.8973 0.126 Uiso 1 1 calc R . .
C39 C 0.6084(5) 0.3464(4) 0.9686(4) 0.0776(15) Uani 1 1 d . . .
H39 H 0.5401 0.3833 0.9779 0.093 Uiso 1 1 calc R . .
C40 C 0.7383(3) 0.5220(3) 1.0018(3) 0.0441(10) Uani 1 1 d . . .
C41 C 0.8169(3) 0.5405(3) 0.8917(3) 0.0462(10) Uani 1 1 d . . .
C42 C 0.9377(4) 0.5354(3) 0.8642(4) 0.0656(13) Uani 1 1 d . . .
H42 H 0.9714 0.5244 0.9139 0.079 Uiso 1 1 calc R . .
C43 C 1.0088(4) 0.5466(4) 0.7627(4) 0.0790(16) Uani 1 1 d . . .
H43 H 1.0900 0.5418 0.7449 0.095 Uiso 1 1 calc R . .
C44 C 0.9604(5) 0.5646(4) 0.6890(4) 0.0856(17) Uani 1 1 d . . .
H44 H 1.0088 0.5727 0.6211 0.103 Uiso 1 1 calc R . .
C45 C 0.8423(5) 0.5709(4) 0.7141(4) 0.0833(16) Uani 1 1 d . . .
H45 H 0.8094 0.5836 0.6636 0.100 Uiso 1 1 calc R . .
C46 C 0.7712(4) 0.5583(3) 0.8151(3) 0.0676(13) Uani 1 1 d . . .
H46 H 0.6900 0.5619 0.8321 0.081 Uiso 1 1 calc R . .
C47 C 0.7821(3) 0.6840(3) 0.9903(3) 0.0470(10) Uani 1 1 d . . .
C48 C 0.8633(4) 0.7151(3) 1.0175(3) 0.0546(11) Uani 1 1 d . . .
H48 H 0.8891 0.6726 1.0687 0.066 Uiso 1 1 calc R . .
C49 C 0.9069(4) 0.8094(3) 0.9688(3) 0.0630(13) Uani 1 1 d . . .
H49 H 0.9607 0.8295 0.9886 0.076 Uiso 1 1 calc R . .
C50 C 0.8709(4) 0.8741(3) 0.8908(3) 0.0588(12) Uani 1 1 d . . .
C51 C 0.7891(4) 0.8420(3) 0.8657(3) 0.0569(12) Uani 1 1 d . . .
H51 H 0.7629 0.8842 0.8146 0.068 Uiso 1 1 calc R . .
C52 C 0.7450(3) 0.7486(3) 0.9146(3) 0.0524(11) Uani 1 1 d . . .
H52 H 0.6895 0.7290 0.8961 0.063 Uiso 1 1 calc R . .
C53 C 1.0196(6) 0.9935(4) 0.8492(6) 0.130(3) Uani 1 1 d . . .
H53A H 1.0079 0.9826 0.9200 0.194 Uiso 1 1 calc R . .
H53B H 1.0391 1.0605 0.8099 0.194 Uiso 1 1 calc R . .
H53C H 1.0825 0.9533 0.8221 0.194 Uiso 1 1 calc R . .
C54 C 0.8941(6) 1.0265(4) 0.7477(5) 0.117(2) Uani 1 1 d . . .
H54A H 0.9336 0.9965 0.6957 0.175 Uiso 1 1 calc R . .
H54B H 0.9244 1.0909 0.7246 0.175 Uiso 1 1 calc R . .
H54C H 0.8113 1.0296 0.7601 0.175 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 F2 1.384(5) . ?
B1 F1 1.390(5) . ?
B1 N2 1.511(5) . ?
B1 N1 1.540(6) . ?
B2 F3 1.346(6) . ?
B2 F4 1.385(6) . ?
B2 N5 1.513(6) . ?
B2 N4 1.551(6) . ?
N1 C1 1.352(5) . ?
N1 C5 1.369(5) . ?
N2 C13 1.360(4) . ?
N2 C20 1.450(5) . ?
N3 C23 1.394(6) . ?
N3 C27 1.417(7) . ?
N3 C26 1.420(6) . ?
N4 C28 1.353(5) . ?
N4 C32 1.363(5) . ?
N5 C40 1.354(5) . ?
N5 C47 1.437(4) . ?
N6 C50 1.407(5) . ?
N6 C53 1.435(7) . ?
N6 C54 1.448(7) . ?
C1 C2 1.347(7) . ?
C2 C3 1.383(7) . ?
C3 C4 1.350(6) . ?
C4 C5 1.398(6) . ?
C5 C6 1.428(5) . ?
C6 C13 1.367(5) . ?
C6 C7 1.505(5) . ?
C7 C8 1.364(6) . ?
C7 C12 1.375(5) . ?
C8 C9 1.389(6) . ?
C9 C10 1.362(7) . ?
C10 C11 1.341(7) . ?
C11 C12 1.385(6) . ?
C13 C14 1.494(5) . ?
C14 C15 1.368(5) . ?
C14 C19 1.372(5) . ?
C15 C16 1.379(6) . ?
C16 C17 1.367(7) . ?
C17 C18 1.358(7) . ?
C18 C19 1.376(6) . ?
C20 C21 1.367(5) . ?
C20 C25 1.377(6) . ?
C21 C22 1.379(6) . ?
C22 C23 1.373(6) . ?
C23 C24 1.394(6) . ?
C24 C25 1.376(6) . ?
C28 C29 1.349(5) . ?
C29 C30 1.381(6) . ?
C30 C31 1.366(6) . ?
C31 C32 1.398(5) . ?
C32 C33 1.432(5) . ?
C33 C40 1.381(5) . ?
C33 C34 1.488(5) . ?
C34 C39 1.372(6) . ?
C34 C35 1.376(6) . ?
C35 C36 1.376(7) . ?
C36 C37 1.357(8) . ?
C37 C38 1.355(9) . ?
C38 C39 1.391(8) . ?
C40 C41 1.496(5) . ?
C41 C46 1.379(6) . ?
C41 C42 1.382(5) . ?
C42 C43 1.386(6) . ?
C43 C44 1.363(7) . ?
C44 C45 1.354(7) . ?
C45 C46 1.377(6) . ?
C47 C52 1.377(5) . ?
C47 C48 1.381(6) . ?
C48 C49 1.390(5) . ?
C49 C50 1.394(6) . ?
C50 C51 1.376(6) . ?
C51 C52 1.382(5) . ?

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
F2 B1 F1 106.7(3) . . ?
F2 B1 N2 111.1(4) . . ?
F1 B1 N2 111.4(3) . . ?
F2 B1 N1 108.2(3) . . ?
F1 B1 N1 108.8(4) . . ?
N2 B1 N1 110.4(3) . . ?
F3 B2 F4 109.2(5) . . ?
F3 B2 N5 111.9(4) . . ?
F4 B2 N5 111.0(4) . . ?
F3 B2 N4 108.6(4) . . ?
F4 B2 N4 106.2(3) . . ?
N5 B2 N4 109.7(4) . . ?
C1 N1 C5 119.8(4) . . ?
C1 N1 B1 116.3(3) . . ?
C5 N1 B1 123.9(3) . . ?
C13 N2 C20 121.2(3) . . ?
C13 N2 B1 122.8(3) . . ?
C20 N2 B1 115.7(3) . . ?
C23 N3 C27 121.1(5) . . ?
C23 N3 C26 120.3(5) . . ?
C27 N3 C26 117.7(5) . . ?
C28 N4 C32 120.1(3) . . ?
C28 N4 B2 116.8(4) . . ?
C32 N4 B2 122.8(3) . . ?
C40 N5 C47 122.2(3) . . ?
C40 N5 B2 122.4(3) . . ?
C47 N5 B2 115.4(3) . . ?
C50 N6 C53 119.3(5) . . ?
C50 N6 C54 118.1(5) . . ?
C53 N6 C54 114.7(4) . . ?
C2 C1 N1 122.5(4) . . ?
C1 C2 C3 118.8(5) . . ?
C4 C3 C2 119.6(5) . . ?
C3 C4 C5 121.2(4) . . ?
N1 C5 C4 118.0(3) . . ?
N1 C5 C6 118.6(4) . . ?
C4 C5 C6 123.3(3) . . ?
C13 C6 C5 121.9(3) . . ?
C13 C6 C7 120.9(3) . . ?
C5 C6 C7 117.3(3) . . ?
C8 C7 C12 117.5(4) . . ?
C8 C7 C6 120.9(4) . . ?
C12 C7 C6 121.6(4) . . ?
C7 C8 C9 121.9(4) . . ?
C10 C9 C8 119.3(5) . . ?
C11 C10 C9 119.8(5) . . ?
C10 C11 C12 121.0(5) . . ?
C7 C12 C11 120.5(5) . . ?
N2 C13 C6 122.2(3) . . ?
N2 C13 C14 118.0(3) . . ?
C6 C13 C14 119.8(3) . . ?
C15 C14 C19 119.1(4) . . ?
C15 C14 C13 119.5(4) . . ?
C19 C14 C13 121.1(4) . . ?
C14 C15 C16 120.4(4) . . ?
C17 C16 C15 120.2(5) . . ?
C18 C17 C16 119.5(4) . . ?
C17 C18 C19 120.7(5) . . ?
C14 C19 C18 120.2(4) . . ?
C21 C20 C25 118.1(4) . . ?
C21 C20 N2 121.2(4) . . ?
C25 C20 N2 120.4(4) . . ?
C20 C21 C22 121.4(4) . . ?
C23 C22 C21 121.3(4) . . ?
C22 C23 C24 117.0(4) . . ?
C22 C23 N3 121.9(4) . . ?
C24 C23 N3 121.2(4) . . ?
C25 C24 C23 121.4(4) . . ?
C24 C25 C20 120.7(4) . . ?
C29 C28 N4 122.7(4) . . ?
C28 C29 C30 118.7(4) . . ?
C31 C30 C29 119.4(4) . . ?
C30 C31 C32 121.1(4) . . ?
N4 C32 C31 117.9(4) . . ?
N4 C32 C33 119.0(3) . . ?
C31 C32 C33 123.1(4) . . ?
C40 C33 C32 121.0(4) . . ?
C40 C33 C34 120.7(3) . . ?
C32 C33 C34 118.3(3) . . ?
C39 C34 C35 117.4(5) . . ?
C39 C34 C33 121.2(4) . . ?
C35 C34 C33 121.4(4) . . ?
C36 C35 C34 120.9(5) . . ?
C37 C36 C35 121.3(6) . . ?
C38 C37 C36 118.8(6) . . ?
C37 C38 C39 120.4(6) . . ?
C34 C39 C38 121.2(6) . . ?
N5 C40 C33 122.2(4) . . ?
N5 C40 C41 119.4(3) . . ?
C33 C40 C41 118.3(4) . . ?
C46 C41 C42 117.8(4) . . ?
C46 C41 C40 121.1(4) . . ?
C42 C41 C40 121.0(4) . . ?
C41 C42 C43 120.1(5) . . ?
C44 C43 C42 120.4(5) . . ?
C45 C44 C43 120.5(5) . . ?
C44 C45 C46 119.4(5) . . ?
C45 C46 C41 121.8(5) . . ?
C52 C47 C48 118.5(4) . . ?
C52 C47 N5 121.9(4) . . ?
C48 C47 N5 119.3(4) . . ?
C47 C48 C49 120.6(4) . . ?
C48 C49 C50 120.9(4) . . ?
C51 C50 C49 117.6(4) . . ?
C51 C50 N6 121.3(4) . . ?
C49 C50 N6 121.1(5) . . ?
C50 C51 C52 121.5(4) . . ?
C47 C52 C51 120.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.063
_database_code_depnum_ccdc_archive 'CCDC 1013249'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_140624c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H29 B N2'
_chemical_formula_weight         512.43

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/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                   10.9565(8)
_cell_length_b                   19.2414(16)
_cell_length_c                   13.7066(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.0020(10)
_cell_angle_gamma                90.00
_cell_volume                     2878.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2877
_cell_measurement_theta_min      2.2785
_cell_measurement_theta_max      21.78

_exptl_crystal_description       ABC
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9681
_exptl_absorpt_correction_T_max  0.9733
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14281
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0610
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         25.02
_reflns_number_total             5066
_reflns_number_gt                2706
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.2000P)²+0.0000P] 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         5066
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1186
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.2325
_refine_ls_wR_factor_gt          0.1591
_refine_ls_goodness_of_fit_ref   0.758
_refine_ls_restrained_S_all      0.758
_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
N1 N 0.19672(19) 0.00083(11) 0.67631(16) 0.0439(6) Uani 1 1 d . . .
N2 N 0.30928(18) 0.11143(10) 0.72402(16) 0.0376(5) Uani 1 1 d . . .
C12 C 0.3283(2) 0.11996(13) 0.6272(2) 0.0388(6) Uani 1 1 d . . .
C4 C 0.2215(3) 0.01136(14) 0.5819(2) 0.0467(7) Uani 1 1 d . . .
C20 C 0.3832(2) 0.14703(12) 0.79934(19) 0.0381(6) Uani 1 1 d . . .
C5 C 0.2795(2) 0.07506(14) 0.5564(2) 0.0440(7) Uani 1 1 d . . .
C25 C 0.3295(2) 0.17686(13) 0.8773(2) 0.0453(7) Uani 1 1 d . . .
H25 H 0.2447 0.1760 0.8783 0.054 Uiso 1 1 calc R . .
C26 C 0.2258(2) 0.03350(13) 0.8606(2) 0.0414(6) Uani 1 1 d . . .
C21 C 0.5101(2) 0.14987(15) 0.8001(2) 0.0497(7) Uani 1 1 d . . .
H21 H 0.5488 0.1294 0.7496 0.060 Uiso 1 1 calc R . .
C13 C 0.3997(2) 0.18129(14) 0.5965(2) 0.0458(7) Uani 1 1 d . . .
C1 C 0.1521(3) -0.06126(15) 0.7026(2) 0.0600(9) Uani 1 1 d . . .
H1 H 0.1385 -0.0681 0.7679 0.072 Uiso 1 1 calc R . .
C32 C 0.0701(2) 0.10555(15) 0.73216(19) 0.0436(7) Uani 1 1 d . . .
C37 C 0.0624(3) 0.17739(16) 0.7229(2) 0.0574(8) Uani 1 1 d . . .
H37 H 0.1346 0.2028 0.7232 0.069 Uiso 1 1 calc R . .
C27 C 0.1455(3) 0.03946(14) 0.9326(2) 0.0477(7) Uani 1 1 d . . .
H27 H 0.0725 0.0635 0.9186 0.057 Uiso 1 1 calc R . .
C24 C 0.4003(3) 0.20777(15) 0.9532(2) 0.0552(8) Uani 1 1 d . . .
H24 H 0.3628 0.2264 1.0056 0.066 Uiso 1 1 calc R . .
C6 C 0.2886(3) 0.08800(14) 0.4500(2) 0.0475(7) Uani 1 1 d . . .
C23 C 0.5243(3) 0.21137(15) 0.9526(2) 0.0602(8) Uani 1 1 d . . .
H23 H 0.5715 0.2327 1.0038 0.072 Uiso 1 1 calc R . .
C33 C -0.0423(2) 0.07134(17) 0.7310(2) 0.0571(8) Uani 1 1 d . . .
H33 H -0.0432 0.0232 0.7365 0.068 Uiso 1 1 calc R . .
C22 C 0.5787(3) 0.18291(16) 0.8752(2) 0.0600(9) Uani 1 1 d . . .
H22 H 0.6632 0.1860 0.8735 0.072 Uiso 1 1 calc R . .
B1 B 0.1998(3) 0.06524(15) 0.7519(2) 0.0410(7) Uani 1 1 d . . .
C34 C -0.1531(3) 0.1071(2) 0.7219(2) 0.0697(10) Uani 1 1 d . . .
H34 H -0.2262 0.0825 0.7214 0.084 Uiso 1 1 calc R . .
C31 C 0.3324(3) -0.00454(15) 0.8863(2) 0.0552(8) Uani 1 1 d . . .
H31 H 0.3891 -0.0101 0.8403 0.066 Uiso 1 1 calc R . .
C14 C 0.3568(3) 0.24710(16) 0.6079(2) 0.0638(9) Uani 1 1 d . . .
H14 H 0.2854 0.2543 0.6384 0.077 Uiso 1 1 calc R . .
C3 C 0.1905(3) -0.04133(16) 0.5136(2) 0.0694(10) Uani 1 1 d . . .
H3 H 0.2026 -0.0340 0.4481 0.083 Uiso 1 1 calc R . .
C28 C 0.1705(3) 0.01079(18) 1.0247(2) 0.0625(9) Uani 1 1 d . . .
H28 H 0.1151 0.0166 1.0718 0.075 Uiso 1 1 calc R . .
C11 C 0.2066(3) 0.13101(17) 0.3984(3) 0.0690(9) Uani 1 1 d . . .
H11 H 0.1470 0.1534 0.4312 0.083 Uiso 1 1 calc R . .
C19 C 0.1263(4) -0.11412(17) 0.6387(3) 0.0773(11) Uani 1 1 d . . .
H19 H 0.0980 -0.1566 0.6598 0.093 Uiso 1 1 calc R . .
C18 C 0.5071(3) 0.17266(18) 0.5512(2) 0.0666(9) Uani 1 1 d . . .
H18 H 0.5370 0.1280 0.5430 0.080 Uiso 1 1 calc R . .
C2 C 0.1434(4) -0.10281(18) 0.5409(3) 0.0800(11) Uani 1 1 d . . .
H2 H 0.1228 -0.1370 0.4945 0.096 Uiso 1 1 calc R . .
C36 C -0.0481(3) 0.2128(2) 0.7134(3) 0.0736(10) Uani 1 1 d . . .
H36 H -0.0487 0.2609 0.7068 0.088 Uiso 1 1 calc R . .
C35 C -0.1556(3) 0.1776(2) 0.7136(3) 0.0757(11) Uani 1 1 d . . .
H35 H -0.2298 0.2014 0.7082 0.091 Uiso 1 1 calc R . .
C29 C 0.2754(3) -0.02592(17) 1.0470(3) 0.0669(9) Uani 1 1 d . . .
H29 H 0.2919 -0.0452 1.1090 0.080 Uiso 1 1 calc R . .
C7 C 0.3746(4) 0.0554(2) 0.3976(3) 0.0794(11) Uani 1 1 d . . .
H7 H 0.4315 0.0254 0.4294 0.095 Uiso 1 1 calc R . .
C30 C 0.3563(3) -0.03410(17) 0.9774(3) 0.0658(9) Uani 1 1 d . . .
H30 H 0.4276 -0.0597 0.9917 0.079 Uiso 1 1 calc R . .
C10 C 0.2099(5) 0.1419(2) 0.2997(3) 0.1006(14) Uani 1 1 d . . .
H10 H 0.1531 0.1717 0.2672 0.121 Uiso 1 1 calc R . .
C15 C 0.4206(5) 0.30373(19) 0.5734(3) 0.0979(14) Uani 1 1 d . . .
H15 H 0.3905 0.3486 0.5794 0.117 Uiso 1 1 calc R . .
C8 C 0.3765(5) 0.0672(3) 0.2975(3) 0.1018(15) Uani 1 1 d . . .
H8 H 0.4351 0.0453 0.2632 0.122 Uiso 1 1 calc R . .
C16 C 0.5277(5) 0.2930(3) 0.5307(3) 0.1086(16) Uani 1 1 d . . .
H16 H 0.5717 0.3307 0.5101 0.130 Uiso 1 1 calc R . .
C9 C 0.2935(6) 0.1105(2) 0.2493(3) 0.1031(16) Uani 1 1 d . . .
H9 H 0.2949 0.1182 0.1824 0.124 Uiso 1 1 calc R . .
C17 C 0.5697(4) 0.2276(3) 0.5185(3) 0.0992(14) Uani 1 1 d . . .
H17 H 0.6411 0.2204 0.4879 0.119 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
N1 C1 1.352(3) . ?
N1 C4 1.360(3) . ?
N1 B1 1.614(4) . ?
N2 C12 1.372(3) . ?
N2 C20 1.430(3) . ?
N2 B1 1.567(3) . ?
C12 C5 1.372(4) . ?
C12 C13 1.495(3) . ?
C4 C3 1.401(4) . ?
C4 C5 1.438(4) . ?
C20 C25 1.389(4) . ?
C20 C21 1.390(4) . ?
C5 C6 1.491(4) . ?
C25 C24 1.377(4) . ?
C26 C27 1.383(4) . ?
C26 C31 1.397(4) . ?
C26 B1 1.613(4) . ?
C21 C22 1.376(4) . ?
C13 C14 1.364(4) . ?
C13 C18 1.388(4) . ?
C1 C19 1.356(4) . ?
C32 C37 1.390(4) . ?
C32 C33 1.395(4) . ?
C32 B1 1.621(4) . ?
C37 C36 1.385(4) . ?
C27 C28 1.384(4) . ?
C24 C23 1.361(4) . ?
C6 C11 1.372(4) . ?
C6 C7 1.384(4) . ?
C23 C22 1.376(4) . ?
C33 C34 1.390(4) . ?
C34 C35 1.363(5) . ?
C31 C30 1.377(4) . ?
C14 C15 1.399(5) . ?
C3 C2 1.356(4) . ?
C28 C29 1.361(4) . ?
C11 C10 1.373(5) . ?
C19 C2 1.387(5) . ?
C18 C17 1.358(5) . ?
C36 C35 1.358(5) . ?
C29 C30 1.366(4) . ?
C7 C8 1.392(5) . ?
C10 C9 1.338(6) . ?
C15 C16 1.372(6) . ?
C8 C9 1.361(6) . ?
C16 C17 1.354(6) . ?

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
C1 N1 C4 119.5(2) . . ?
C1 N1 B1 119.7(2) . . ?
C4 N1 B1 120.1(2) . . ?
C12 N2 C20 121.1(2) . . ?
C12 N2 B1 119.2(2) . . ?
C20 N2 B1 119.6(2) . . ?
C5 C12 N2 121.7(2) . . ?
C5 C12 C13 118.6(2) . . ?
N2 C12 C13 119.6(2) . . ?
N1 C4 C3 118.1(2) . . ?
N1 C4 C5 119.2(2) . . ?
C3 C4 C5 122.7(3) . . ?
C25 C20 C21 118.0(2) . . ?
C25 C20 N2 120.1(2) . . ?
C21 C20 N2 121.8(2) . . ?
C12 C5 C4 121.2(2) . . ?
C12 C5 C6 122.1(2) . . ?
C4 C5 C6 116.7(2) . . ?
C24 C25 C20 120.7(3) . . ?
C27 C26 C31 115.7(3) . . ?
C27 C26 B1 123.7(2) . . ?
C31 C26 B1 120.6(2) . . ?
C22 C21 C20 120.3(3) . . ?
C14 C13 C18 118.4(3) . . ?
C14 C13 C12 120.5(3) . . ?
C18 C13 C12 121.0(3) . . ?
N1 C1 C19 123.4(3) . . ?
C37 C32 C33 115.0(3) . . ?
C37 C32 B1 122.4(2) . . ?
C33 C32 B1 122.4(3) . . ?
C32 C37 C36 122.9(3) . . ?
C26 C27 C28 122.1(3) . . ?
C25 C24 C23 121.0(3) . . ?
C11 C6 C7 116.8(3) . . ?
C11 C6 C5 120.6(3) . . ?
C7 C6 C5 122.6(3) . . ?
C22 C23 C24 119.0(3) . . ?
C32 C33 C34 122.0(3) . . ?
C23 C22 C21 121.1(3) . . ?
N2 B1 N1 104.6(2) . . ?
N2 B1 C26 111.3(2) . . ?
N1 B1 C26 107.1(2) . . ?
N2 B1 C32 111.5(2) . . ?
N1 B1 C32 107.0(2) . . ?
C26 B1 C32 114.7(2) . . ?
C35 C34 C33 120.7(3) . . ?
C30 C31 C26 122.3(3) . . ?
C13 C14 C15 119.9(3) . . ?
C2 C3 C4 121.5(3) . . ?
C29 C28 C27 120.5(3) . . ?
C6 C11 C10 121.9(4) . . ?
C2 C19 C1 117.9(3) . . ?
C17 C18 C13 121.8(4) . . ?
C19 C2 C3 119.3(3) . . ?
C35 C36 C37 120.4(4) . . ?
C36 C35 C34 119.0(3) . . ?
C28 C29 C30 119.3(3) . . ?
C6 C7 C8 120.4(4) . . ?
C31 C30 C29 120.1(3) . . ?
C9 C10 C11 121.2(5) . . ?
C16 C15 C14 119.8(4) . . ?
C9 C8 C7 120.8(4) . . ?
C17 C16 C15 120.4(4) . . ?
C10 C9 C8 118.9(4) . . ?
C16 C17 C18 119.7(4) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.039
_database_code_depnum_ccdc_archive 'CCDC 1013250'
