# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 1451327'
_audit_update_record             
;
2016-02-02 deposited with the CCDC.
2016-06-02 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            1b
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H15 B F15 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         661.22

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   10.7816(3)
_cell_length_b                   17.0803(4)
_cell_length_c                   14.4528(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.7450(10)
_cell_angle_gamma                90
_cell_volume                     2655.84(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9958
_cell_measurement_theta_min      2.2866
_cell_measurement_theta_max      25.6056
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.220
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1320

_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      200.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  BrukerKappaApex2
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            43375
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_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.
;

_reflns_number_total             4860
_reflns_number_gt                3940
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_gt          0.1378
_refine_ls_wR_factor_ref         0.1570
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_number_reflns         4860
_refine_ls_number_parameters     409
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0911P)²+2.5447P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.000
_refine_diff_density_min         -0.551
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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

_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.3026(2) 0.15447(14) 0.66071(17) 0.0238(5) Uani d . 1 . .
C C1 0.2919(2) 0.06590(13) 0.81864(15) 0.0261(5) Uani d . 1 . .
C C2 0.3440(3) 0.00410(16) 0.86816(18) 0.0393(6) Uani d . 1 . .
H H2 0.3978 -0.0312 0.8395 0.047 Uiso calc R 1 . .
C C3 0.3179(3) -0.00667(17) 0.95989(18) 0.0427(7) Uani d . 1 . .
H H3 0.3551 -0.0492 0.9937 0.051 Uiso calc R 1 . .
C C4 0.2388(2) 0.04343(15) 1.00341(16) 0.0323(5) Uani d . 1 . .
C C5 0.1885(2) 0.10536(14) 0.95141(16) 0.0301(5) Uani d . 1 . .
H H5 0.1349 0.141 0.9797 0.036 Uiso calc R 1 . .
C C6 0.2136(2) 0.11713(14) 0.85966(16) 0.0286(5) Uani d . 1 . .
H H6 0.1774 0.1599 0.8256 0.034 Uiso calc R 1 . .
C C7 0.2105(3) 0.03298(19) 1.10534(18) 0.0477(7) Uani d . 1 . .
C C8 0.2772(5) 0.1018(4) 1.1610(2) 0.1029(19) Uani d . 1 . .
H H8A 0.2601 0.0977 1.2266 0.154 Uiso calc R 1 . .
H H8B 0.2459 0.152 1.1363 0.154 Uiso calc R 1 . .
H H8C 0.367 0.0987 1.1548 0.154 Uiso calc R 1 . .
C C9 0.0754(3) 0.0457(3) 1.1202(2) 0.0666(10) Uani d . 1 . .
H H9A 0.0253 0.0075 1.0835 0.1 Uiso calc R 1 . .
H H9B 0.0514 0.0988 1.1007 0.1 Uiso calc R 1 . .
H H9C 0.0615 0.0389 1.1861 0.1 Uiso calc R 1 . .
C C10 0.2539(9) -0.0431(4) 1.1431(4) 0.196(5) Uani d . 1 . .
H H10A 0.243 -0.0447 1.2099 0.294 Uiso calc R 1 . .
H H10B 0.3421 -0.0499 1.1323 0.294 Uiso calc R 1 . .
H H10C 0.2055 -0.0853 1.1122 0.294 Uiso calc R 1 . .
C C11 0.3753(2) 0.22042(13) 0.72563(15) 0.0264(5) Uani d . 1 . .
C C12 0.3246(2) 0.28771(14) 0.76042(16) 0.0308(5) Uani d . 1 . .
C C13 0.3920(3) 0.34188(14) 0.81392(18) 0.0382(6) Uani d . 1 . .
C C14 0.5167(3) 0.33054(16) 0.83495(18) 0.0422(7) Uani d . 1 . .
C C15 0.5719(3) 0.26395(17) 0.80315(19) 0.0414(6) Uani d . 1 . .
C C16 0.5008(2) 0.21132(14) 0.75068(17) 0.0325(5) Uani d . 1 . .
C C17 0.3702(2) 0.13726(13) 0.56344(15) 0.0230(5) Uani d . 1 . .
C C18 0.3470(2) 0.06923(13) 0.51307(15) 0.0241(5) Uani d . 1 . .
C C19 0.3991(2) 0.05086(13) 0.43130(15) 0.0262(5) Uani d . 1 . .
C C20 0.4769(2) 0.10397(15) 0.39408(16) 0.0303(5) Uani d . 1 . .
C C21 0.5004(2) 0.17365(16) 0.43853(17) 0.0344(6) Uani d . 1 . .
C C22 0.4485(2) 0.18886(14) 0.52153(16) 0.0289(5) Uani d . 1 . .
C C23 0.1568(2) 0.17191(13) 0.62919(15) 0.0270(5) Uani d . 1 . .
C C24 0.0553(2) 0.12481(15) 0.64150(17) 0.0328(5) Uani d . 1 . .
C C25 -0.0642(3) 0.14140(18) 0.6074(2) 0.0446(7) Uani d . 1 . .
C C26 -0.0869(3) 0.20843(19) 0.5567(2) 0.0479(7) Uani d . 1 . .
C C27 0.0099(3) 0.25764(17) 0.5407(2) 0.0423(7) Uani d . 1 . .
C C28 0.1278(2) 0.23830(15) 0.57573(17) 0.0323(5) Uani d . 1 . .
F F1 0.20303(14) 0.30413(9) 0.74462(11) 0.0409(4) Uani d . 1 . .
F F2 0.33547(19) 0.40550(9) 0.84606(13) 0.0588(5) Uani d . 1 . .
F F3 0.5835(2) 0.38278(11) 0.88571(13) 0.0626(5) Uani d . 1 . .
F F4 0.69360(17) 0.25128(12) 0.82352(14) 0.0629(5) Uani d . 1 . .
F F5 0.56037(15) 0.14716(9) 0.72113(12) 0.0459(4) Uani d . 1 . .
F F6 0.26863(15) 0.01475(8) 0.54464(9) 0.0374(4) Uani d . 1 . .
F F7 0.37761(15) -0.01782(8) 0.38896(10) 0.0387(4) Uani d . 1 . .
F F8 0.53017(15) 0.08652(10) 0.31530(10) 0.0451(4) Uani d . 1 . .
F F9 0.57363(18) 0.22683(11) 0.40155(11) 0.0569(5) Uani d . 1 . .
F F10 0.47815(16) 0.25878(8) 0.55987(10) 0.0423(4) Uani d . 1 . .
F F11 0.06934(15) 0.05668(9) 0.68904(11) 0.0437(4) Uani d . 1 . .
F F12 -0.15709(16) 0.09224(13) 0.62279(15) 0.0684(6) Uani d . 1 . .
F F13 -0.20215(17) 0.22483(14) 0.52220(17) 0.0750(6) Uani d . 1 . .
F F14 -0.01006(18) 0.32302(11) 0.49088(14) 0.0602(5) Uani d . 1 . .
F F15 0.21966(14) 0.28813(9) 0.55637(11) 0.0407(4) Uani d . 1 . .
N N1 0.31804(19) 0.07218(11) 0.71949(12) 0.0274(4) Uani d . 1 . .
H H1A 0.2684 0.0358 0.6881 0.033 Uiso calc R 1 . .
H H1B 0.3988 0.0559 0.7151 0.033 Uiso calc R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 C11 . 1.633(3) ?
B1 C23 . 1.635(3) ?
B1 N1 . 1.645(3) ?
B1 C17 . 1.652(3) ?
C1 C2 . 1.375(3) ?
C1 C6 . 1.376(3) ?
C1 N1 . 1.482(3) ?
C2 C3 . 1.385(4) ?
C2 H2 . 0.95 ?
C3 C4 . 1.388(4) ?
C3 H3 . 0.95 ?
C4 C5 . 1.387(3) ?
C4 C7 . 1.534(3) ?
C5 C6 . 1.385(3) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
C7 C10 . 1.474(5) ?
C7 C9 . 1.502(5) ?
C7 C8 . 1.572(6) ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
C9 H9A . 0.98 ?
C9 H9B . 0.98 ?
C9 H9C . 0.98 ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 C12 . 1.382(3) ?
C11 C16 . 1.387(4) ?
C12 F1 . 1.345(3) ?
C12 C13 . 1.382(4) ?
C13 F2 . 1.344(3) ?
C13 C14 . 1.372(4) ?
C14 F3 . 1.336(3) ?
C14 C15 . 1.376(4) ?
C15 F4 . 1.343(3) ?
C15 C16 . 1.377(4) ?
C16 F5 . 1.354(3) ?
C17 C18 . 1.385(3) ?
C17 C22 . 1.386(3) ?
C18 F6 . 1.356(3) ?
C18 C19 . 1.377(3) ?
C19 F7 . 1.336(3) ?
C19 C20 . 1.369(3) ?
C20 F8 . 1.342(3) ?
C20 C21 . 1.368(4) ?
C21 F9 . 1.338(3) ?
C21 C22 . 1.381(3) ?
C22 F10 . 1.346(3) ?
C23 C24 . 1.379(3) ?
C23 C28 . 1.396(3) ?
C24 F11 . 1.355(3) ?
C24 C25 . 1.378(4) ?
C25 F12 . 1.337(3) ?
C25 C26 . 1.373(4) ?
C26 F13 . 1.338(3) ?
C26 C27 . 1.372(4) ?
C27 F14 . 1.338(3) ?
C27 C28 . 1.378(4) ?
C28 F15 . 1.349(3) ?
N1 H1A . 0.92 ?
N1 H1B . 0.92 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 B1 C23 . . 116.80(19) ?
C11 B1 N1 . . 105.30(18) ?
C23 B1 N1 . . 111.26(18) ?
C11 B1 C17 . . 112.95(18) ?
C23 B1 C17 . . 105.37(18) ?
N1 B1 C17 . . 104.60(17) ?
C2 C1 C6 . . 120.3(2) ?
C2 C1 N1 . . 117.5(2) ?
C6 C1 N1 . . 122.1(2) ?
C1 C2 C3 . . 119.9(2) ?
C1 C2 H2 . . 120.0 ?
C3 C2 H2 . . 120.0 ?
C2 C3 C4 . . 121.4(2) ?
C2 C3 H3 . . 119.3 ?
C4 C3 H3 . . 119.3 ?
C5 C4 C3 . . 117.0(2) ?
C5 C4 C7 . . 120.9(2) ?
C3 C4 C7 . . 122.0(2) ?
C6 C5 C4 . . 122.4(2) ?
C6 C5 H5 . . 118.8 ?
C4 C5 H5 . . 118.8 ?
C1 C6 C5 . . 118.9(2) ?
C1 C6 H6 . . 120.5 ?
C5 C6 H6 . . 120.5 ?
C10 C7 C9 . . 111.2(4) ?
C10 C7 C4 . . 112.3(3) ?
C9 C7 C4 . . 112.1(2) ?
C10 C7 C8 . . 110.3(5) ?
C9 C7 C8 . . 103.5(3) ?
C4 C7 C8 . . 107.0(3) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C7 C9 H9A . . 109.5 ?
C7 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C7 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C7 C10 H10A . . 109.5 ?
C7 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C7 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C12 C11 C16 . . 113.6(2) ?
C12 C11 B1 . . 126.6(2) ?
C16 C11 B1 . . 119.7(2) ?
F1 C12 C11 . . 121.1(2) ?
F1 C12 C13 . . 115.3(2) ?
C11 C12 C13 . . 123.7(2) ?
F2 C13 C14 . . 119.9(2) ?
F2 C13 C12 . . 120.0(3) ?
C14 C13 C12 . . 120.1(2) ?
F3 C14 C13 . . 120.8(3) ?
F3 C14 C15 . . 120.4(3) ?
C13 C14 C15 . . 118.8(2) ?
F4 C15 C14 . . 119.8(3) ?
F4 C15 C16 . . 121.1(3) ?
C14 C15 C16 . . 119.1(3) ?
F5 C16 C15 . . 116.3(2) ?
F5 C16 C11 . . 118.9(2) ?
C15 C16 C11 . . 124.7(2) ?
C18 C17 C22 . . 113.46(19) ?
C18 C17 B1 . . 121.45(19) ?
C22 C17 B1 . . 125.01(19) ?
F6 C18 C19 . . 115.49(19) ?
F6 C18 C17 . . 119.61(19) ?
C19 C18 C17 . . 124.9(2) ?
F7 C19 C20 . . 119.6(2) ?
F7 C19 C18 . . 121.6(2) ?
C20 C19 C18 . . 118.7(2) ?
F8 C20 C21 . . 121.0(2) ?
F8 C20 C19 . . 119.6(2) ?
C21 C20 C19 . . 119.4(2) ?
F9 C21 C20 . . 119.9(2) ?
F9 C21 C22 . . 120.2(2) ?
C20 C21 C22 . . 119.9(2) ?
F10 C22 C21 . . 115.2(2) ?
F10 C22 C17 . . 121.3(2) ?
C21 C22 C17 . . 123.5(2) ?
C24 C23 C28 . . 113.2(2) ?
C24 C23 B1 . . 127.9(2) ?
C28 C23 B1 . . 118.6(2) ?
F11 C24 C25 . . 115.4(2) ?
F11 C24 C23 . . 120.2(2) ?
C25 C24 C23 . . 124.4(2) ?
F12 C25 C26 . . 120.2(3) ?
F12 C25 C24 . . 120.3(3) ?
C26 C25 C24 . . 119.5(3) ?
F13 C26 C27 . . 120.5(3) ?
F13 C26 C25 . . 120.2(3) ?
C27 C26 C25 . . 119.3(3) ?
F14 C27 C26 . . 120.3(3) ?
F14 C27 C28 . . 120.6(3) ?
C26 C27 C28 . . 119.0(3) ?
F15 C28 C27 . . 116.4(2) ?
F15 C28 C23 . . 119.1(2) ?
C27 C28 C23 . . 124.5(2) ?
C1 N1 B1 . . 122.81(17) ?
C1 N1 H1A . . 106.6 ?
B1 N1 H1A . . 106.6 ?
C1 N1 H1B . . 106.6 ?
B1 N1 H1B . . 106.6 ?
H1A N1 H1B . . 106.6 ?

_chemical_properties_physical    Air-sensitive
####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1451328'
_audit_update_record             
;
2016-02-02 deposited with the CCDC.
2016-06-02 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            2a
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H21 B F15 N3'
_chemical_formula_iupac          ?
_chemical_formula_weight         731.32

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   10.9239(7)
_cell_length_b                   19.2190(11)
_cell_length_c                   14.3968(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.539(3)
_cell_angle_gamma                90
_cell_volume                     3016.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      2.2740
_cell_measurement_theta_max      26.3066
_cell_measurement_temperature    110.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1472

_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      110.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  BrukerKappaApex2
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            48626
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_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.
;

_reflns_number_total             5530
_reflns_number_gt                4569
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0942
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_number_reflns         5530
_refine_ls_number_parameters     455
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0550P)²+1.3622P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.335
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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

_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.09673(17) 0.28201(9) 0.94927(13) 0.0146(4) Uani d . 1 . .
C C1 0.11643(14) 0.32514(8) 1.04861(11) 0.0142(3) Uani d . 1 . .
C C2 0.07624(15) 0.39199(8) 1.06708(11) 0.0155(3) Uani d . 1 . .
C C3 0.09674(15) 0.42549(8) 1.15172(12) 0.0171(4) Uani d . 1 . .
C C4 0.16187(15) 0.39299(9) 1.22373(11) 0.0182(4) Uani d . 1 . .
C C5 0.20751(15) 0.32725(9) 1.20890(11) 0.0175(4) Uani d . 1 . .
C C6 0.18468(15) 0.29591(8) 1.12350(11) 0.0159(3) Uani d . 1 . .
C C7 0.02640(14) 0.20641(8) 0.96067(11) 0.0148(3) Uani d . 1 . .
C C8 -0.02404(16) 0.18003(9) 1.04000(12) 0.0180(4) Uani d . 1 . .
C C9 -0.08281(17) 0.11634(9) 1.04311(12) 0.0228(4) Uani d . 1 . .
C C10 -0.09468(16) 0.07527(9) 0.96507(13) 0.0219(4) Uani d . 1 . .
C C11 -0.05036(16) 0.09941(9) 0.88395(12) 0.0190(4) Uani d . 1 . .
C C12 0.00588(15) 0.16356(8) 0.88307(11) 0.0160(3) Uani d . 1 . .
C C13 0.00413(15) 0.32321(8) 0.87086(11) 0.0156(3) Uani d . 1 . .
C C14 -0.11618(16) 0.33637(8) 0.89283(12) 0.0176(4) Uani d . 1 . .
C C15 -0.20478(15) 0.36498(8) 0.83229(13) 0.0200(4) Uani d . 1 . .
C C16 -0.17704(16) 0.38241(8) 0.74352(12) 0.0214(4) Uani d . 1 . .
C C17 -0.06008(17) 0.37059(9) 0.71736(12) 0.0206(4) Uani d . 1 . .
C C18 0.02647(15) 0.34161(8) 0.78035(12) 0.0173(4) Uani d . 1 . .
C C19 0.27541(15) 0.20441(8) 0.87946(12) 0.0157(3) Uani d . 1 . .
C C20 0.31177(15) 0.20426(9) 0.78823(12) 0.0194(4) Uani d . 1 . .
H H20 0.3116 0.2463 0.7536 0.023 Uiso calc R 1 . .
C C21 0.34813(16) 0.14267(10) 0.74841(13) 0.0244(4) Uani d . 1 . .
H H21 0.372 0.1425 0.6861 0.029 Uiso calc R 1 . .
C C22 0.34994(17) 0.08118(10) 0.79911(14) 0.0270(4) Uani d . 1 . .
H H22 0.375 0.039 0.7716 0.032 Uiso calc R 1 . .
C C23 0.31492(16) 0.08171(9) 0.89004(13) 0.0240(4) Uani d . 1 . .
H H23 0.3166 0.0397 0.925 0.029 Uiso calc R 1 . .
C C24 0.27742(15) 0.14314(9) 0.93049(12) 0.0185(4) Uani d . 1 . .
H H24 0.2533 0.1432 0.9928 0.022 Uiso calc R 1 . .
C C25 0.31696(15) 0.32159(8) 0.92011(11) 0.0150(3) Uani d . 1 . .
C C26 0.35673(16) 0.44999(8) 0.92732(12) 0.0193(4) Uani d . 1 . .
H H26 0.4229 0.4388 0.9762 0.023 Uiso calc R 1 . .
C C27 0.27743(19) 0.50803(9) 0.96338(15) 0.0296(4) Uani d . 1 . .
H H27A 0.2068 0.5158 0.9193 0.044 Uiso calc R 1 . .
H H27B 0.3259 0.5509 0.97 0.044 Uiso calc R 1 . .
H H27C 0.2486 0.4947 1.024 0.044 Uiso calc R 1 . .
C C28 0.41649(17) 0.47218(10) 0.83893(13) 0.0257(4) Uani d . 1 . .
H H28A 0.4636 0.4332 0.8156 0.038 Uiso calc R 1 . .
H H28B 0.4714 0.5116 0.8529 0.038 Uiso calc R 1 . .
H H28C 0.3528 0.4859 0.7916 0.038 Uiso calc R 1 . .
C C29 0.49541(16) 0.25654(9) 0.99718(12) 0.0186(4) Uani d . 1 . .
H H29 0.429 0.2271 1.0215 0.022 Uiso calc R 1 . .
C C30 0.55973(18) 0.29512(10) 1.07882(13) 0.0258(4) Uani d . 1 . .
H H30A 0.6244 0.3248 1.0561 0.039 Uiso calc R 1 . .
H H30B 0.5961 0.2614 1.1235 0.039 Uiso calc R 1 . .
H H30C 0.5001 0.3239 1.1094 0.039 Uiso calc R 1 . .
C C31 0.58258(17) 0.20955(9) 0.94839(13) 0.0253(4) Uani d . 1 . .
H H31A 0.5378 0.1857 0.8966 0.038 Uiso calc R 1 . .
H H31B 0.6176 0.1751 0.9926 0.038 Uiso calc R 1 . .
H H31C 0.6487 0.2375 0.9244 0.038 Uiso calc R 1 . .
F F1 0.01469(9) 0.42984(5) 1.00034(6) 0.0200(2) Uani d . 1 . .
F F2 0.05239(10) 0.49013(5) 1.16341(7) 0.0234(2) Uani d . 1 . .
F F3 0.17907(9) 0.42414(5) 1.30688(7) 0.0244(2) Uani d . 1 . .
F F4 0.27218(9) 0.29389(5) 1.27783(7) 0.0237(2) Uani d . 1 . .
F F5 0.23121(9) 0.23092(5) 1.11530(6) 0.0203(2) Uani d . 1 . .
F F6 -0.02077(10) 0.21663(5) 1.12040(7) 0.0251(2) Uani d . 1 . .
F F7 -0.12904(11) 0.09458(6) 1.12281(8) 0.0362(3) Uani d . 1 . .
F F8 -0.14991(11) 0.01291(5) 0.96769(8) 0.0334(3) Uani d . 1 . .
F F9 -0.06250(10) 0.06099(5) 0.80579(7) 0.0270(2) Uani d . 1 . .
F F10 0.04144(9) 0.18485(5) 0.79943(6) 0.0195(2) Uani d . 1 . .
F F11 -0.15111(9) 0.32078(5) 0.97925(7) 0.0212(2) Uani d . 1 . .
F F12 -0.31988(9) 0.37637(5) 0.85965(8) 0.0284(3) Uani d . 1 . .
F F13 -0.26238(10) 0.41097(5) 0.68406(8) 0.0314(3) Uani d . 1 . .
F F14 -0.02992(11) 0.38720(6) 0.63081(7) 0.0303(3) Uani d . 1 . .
F F15 0.13944(9) 0.33202(5) 0.74750(7) 0.0224(2) Uani d . 1 . .
N N1 0.23380(12) 0.26960(7) 0.91811(9) 0.0139(3) Uani d . 1 . .
N N2 0.27998(13) 0.38765(7) 0.91080(10) 0.0167(3) Uani d . 1 . .
H H2 0.2024 0.3946 0.8931 0.02 Uiso calc R 1 . .
N N3 0.43804(13) 0.30869(7) 0.93208(10) 0.0176(3) Uani d . 1 . .
H H3 0.4872 0.3332 0.8986 0.021 Uiso calc R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 N1 . 1.607(2) ?
B1 C1 . 1.655(2) ?
B1 C7 . 1.657(2) ?
B1 C13 . 1.668(2) ?
C1 C2 . 1.389(2) ?
C1 C6 . 1.391(2) ?
C2 F1 . 1.3508(18) ?
C2 C3 . 1.384(2) ?
C3 F2 . 1.3477(19) ?
C3 C4 . 1.371(2) ?
C4 F3 . 1.3412(19) ?
C4 C5 . 1.380(2) ?
C5 F4 . 1.3446(19) ?
C5 C6 . 1.378(2) ?
C6 F5 . 1.3563(18) ?
C7 C8 . 1.394(2) ?
C7 C12 . 1.395(2) ?
C8 F6 . 1.3530(19) ?
C8 C9 . 1.384(2) ?
C9 F7 . 1.348(2) ?
C9 C10 . 1.373(3) ?
C10 F8 . 1.3434(19) ?
C10 C11 . 1.372(3) ?
C11 F9 . 1.3456(19) ?
C11 C12 . 1.378(2) ?
C12 F10 . 1.3513(19) ?
C13 C18 . 1.386(2) ?
C13 C14 . 1.394(2) ?
C14 F11 . 1.357(2) ?
C14 C15 . 1.376(2) ?
C15 F12 . 1.358(2) ?
C15 C16 . 1.373(3) ?
C16 F13 . 1.3434(19) ?
C16 C17 . 1.373(3) ?
C17 F14 . 1.347(2) ?
C17 C18 . 1.386(2) ?
C18 F15 . 1.361(2) ?
C19 C24 . 1.387(2) ?
C19 C20 . 1.395(2) ?
C19 N1 . 1.455(2) ?
C20 C21 . 1.384(2) ?
C21 C22 . 1.389(3) ?
C22 C23 . 1.386(3) ?
C23 C24 . 1.389(2) ?
C25 N2 . 1.337(2) ?
C25 N3 . 1.346(2) ?
C25 N1 . 1.349(2) ?
C26 N2 . 1.473(2) ?
C26 C27 . 1.523(3) ?
C26 C28 . 1.526(2) ?
C29 N3 . 1.484(2) ?
C29 C31 . 1.516(2) ?
C29 C30 . 1.524(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 B1 C1 . . 104.00(12) ?
N1 B1 C7 . . 110.07(12) ?
C1 B1 C7 . . 112.95(13) ?
N1 B1 C13 . . 114.71(13) ?
C1 B1 C13 . . 112.83(13) ?
C7 B1 C13 . . 102.58(12) ?
C2 C1 C6 . . 112.70(14) ?
C2 C1 B1 . . 127.07(14) ?
C6 C1 B1 . . 120.15(14) ?
F1 C2 C3 . . 114.96(14) ?
F1 C2 C1 . . 120.76(14) ?
C3 C2 C1 . . 124.26(15) ?
F2 C3 C4 . . 119.95(14) ?
F2 C3 C2 . . 119.92(15) ?
C4 C3 C2 . . 120.13(15) ?
F3 C4 C3 . . 120.60(15) ?
F3 C4 C5 . . 120.98(15) ?
C3 C4 C5 . . 118.41(15) ?
F4 C5 C6 . . 120.53(14) ?
F4 C5 C4 . . 120.05(14) ?
C6 C5 C4 . . 119.41(15) ?
F5 C6 C5 . . 115.59(14) ?
F5 C6 C1 . . 119.36(14) ?
C5 C6 C1 . . 125.02(15) ?
C8 C7 C12 . . 112.92(15) ?
C8 C7 B1 . . 127.55(14) ?
C12 C7 B1 . . 119.41(14) ?
F6 C8 C9 . . 114.83(15) ?
F6 C8 C7 . . 121.40(14) ?
C9 C8 C7 . . 123.76(16) ?
F7 C9 C10 . . 119.79(15) ?
F7 C9 C8 . . 120.04(16) ?
C10 C9 C8 . . 120.17(16) ?
F8 C10 C11 . . 120.54(16) ?
F8 C10 C9 . . 120.65(16) ?
C11 C10 C9 . . 118.80(15) ?
F9 C11 C10 . . 120.29(15) ?
F9 C11 C12 . . 120.29(15) ?
C10 C11 C12 . . 119.42(15) ?
F10 C12 C11 . . 115.59(14) ?
F10 C12 C7 . . 119.61(14) ?
C11 C12 C7 . . 124.79(15) ?
C18 C13 C14 . . 112.96(15) ?
C18 C13 B1 . . 128.50(15) ?
C14 C13 B1 . . 118.26(14) ?
F11 C14 C15 . . 116.24(15) ?
F11 C14 C13 . . 119.36(14) ?
C15 C14 C13 . . 124.40(16) ?
F12 C15 C16 . . 119.48(15) ?
F12 C15 C14 . . 120.53(16) ?
C16 C15 C14 . . 119.99(16) ?
F13 C16 C17 . . 120.91(16) ?
F13 C16 C15 . . 120.56(16) ?
C17 C16 C15 . . 118.52(15) ?
F14 C17 C16 . . 119.97(15) ?
F14 C17 C18 . . 120.31(16) ?
C16 C17 C18 . . 119.72(16) ?
F15 C18 C17 . . 115.06(15) ?
F15 C18 C13 . . 120.53(14) ?
C17 C18 C13 . . 124.41(16) ?
C24 C19 C20 . . 120.04(15) ?
C24 C19 N1 . . 121.56(15) ?
C20 C19 N1 . . 118.39(14) ?
C21 C20 C19 . . 119.82(16) ?
C20 C21 C22 . . 120.35(17) ?
C23 C22 C21 . . 119.63(16) ?
C22 C23 C24 . . 120.51(17) ?
C19 C24 C23 . . 119.65(16) ?
N2 C25 N3 . . 118.44(14) ?
N2 C25 N1 . . 120.15(15) ?
N3 C25 N1 . . 121.41(14) ?
N2 C26 C27 . . 108.71(14) ?
N2 C26 C28 . . 111.16(14) ?
C27 C26 C28 . . 111.17(15) ?
N3 C29 C31 . . 111.25(14) ?
N3 C29 C30 . . 108.37(13) ?
C31 C29 C30 . . 111.98(15) ?
C25 N1 C19 . . 114.83(13) ?
C25 N1 B1 . . 121.44(13) ?
C19 N1 B1 . . 123.57(12) ?
C25 N2 C26 . . 126.22(14) ?
C25 N3 C29 . . 125.33(14) ?
####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1451329'
_audit_update_record             
;
2016-02-02 deposited with the CCDC.
2016-06-02 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            3a
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H21 N3'
_chemical_formula_iupac          ?
_chemical_formula_weight         219.33

_chemical_melting_point          ?

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

_cell_length_a                   14.1014(5)
_cell_length_b                   11.3796(5)
_cell_length_c                   8.7040(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.869(2)
_cell_angle_gamma                90
_cell_volume                     1329.34(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6062
_cell_measurement_theta_min      2.3465
_cell_measurement_theta_max      26.3651
_cell_measurement_temperature    210.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.180
_exptl_crystal_density_diffrn    1.096
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480

_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      210.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  BrukerKappaApex2
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            13122
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_full        25.33
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10

_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.
;

_reflns_number_total             2435
_reflns_number_gt                2085
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1189
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_number_reflns         2435
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0654P)²+0.4029P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.312
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.24302(9) 0.96979(11) 0.32893(14) 0.0287(3) Uani d . 1 . .
C C2 0.17848(10) 0.99338(13) 0.41829(16) 0.0354(3) Uani d . 1 . .
H H2 0.1496 0.9308 0.4585 0.042 Uiso calc R 1 . .
C C3 0.15634(12) 1.10802(14) 0.44871(18) 0.0444(4) Uani d . 1 . .
H H3 0.1125 1.1224 0.509 0.053 Uiso calc R 1 . .
C C4 0.19801(13) 1.20093(14) 0.39125(19) 0.0473(4) Uani d . 1 . .
H H4 0.1828 1.2786 0.4119 0.057 Uiso calc R 1 . .
C C5 0.26233(12) 1.17884(13) 0.30296(19) 0.0439(4) Uani d . 1 . .
H H5 0.2908 1.242 0.263 0.053 Uiso calc R 1 . .
C C6 0.28541(11) 1.06470(13) 0.27259(17) 0.0367(3) Uani d . 1 . .
H H6 0.3301 1.0511 0.2135 0.044 Uiso calc R 1 . .
C C7 0.27301(9) 0.80939(11) 0.17518(15) 0.0285(3) Uani d . 1 . .
C C8 0.40747(10) 0.66606(12) 0.30776(17) 0.0343(3) Uani d . 1 . .
H H8 0.3857 0.6628 0.4055 0.041 Uiso calc R 1 . .
C C9 0.43070(14) 0.54219(15) 0.2654(2) 0.0589(5) Uani d . 1 . .
H H9A 0.3731 0.4923 0.2533 0.088 Uiso calc R 1 . .
H H9B 0.4869 0.5116 0.3509 0.088 Uiso calc R 1 . .
H H9C 0.447 0.5435 0.165 0.088 Uiso calc R 1 . .
C C10 0.49748(12) 0.74512(16) 0.3412(2) 0.0561(5) Uani d . 1 . .
H H10A 0.52 0.7483 0.2466 0.084 Uiso calc R 1 . .
H H10B 0.5504 0.7144 0.4319 0.084 Uiso calc R 1 . .
H H10C 0.4799 0.8236 0.3666 0.084 Uiso calc R 1 . .
C C11 0.12822(10) 0.91080(12) -0.02321(16) 0.0352(3) Uani d . 1 . .
H H11 0.1305 0.9768 0.052 0.042 Uiso calc R 1 . .
C C12 0.11070(13) 0.96032(14) -0.19080(19) 0.0479(4) Uani d . 1 . .
H H12A 0.1644 1.0137 -0.1903 0.072 Uiso calc R 1 . .
H H12B 0.0479 1.0024 -0.2238 0.072 Uiso calc R 1 . .
H H12C 0.1086 0.8966 -0.2658 0.072 Uiso calc R 1 . .
C C13 0.04596(12) 0.82785(16) -0.0164(2) 0.0538(5) Uani d . 1 . .
H H13A 0.044 0.7616 -0.0874 0.081 Uiso calc R 1 . .
H H13B -0.0174 0.8688 -0.0508 0.081 Uiso calc R 1 . .
H H13C 0.0585 0.7999 0.0933 0.081 Uiso calc R 1 . .
N N1 0.27058(8) 0.85241(9) 0.31295(13) 0.0312(3) Uani d . 1 . .
N N2 0.32501(9) 0.70931(10) 0.17345(15) 0.0350(3) Uani d . 1 . .
N N3 0.22596(8) 0.85306(11) 0.02397(14) 0.0341(3) Uani d . 1 . .
H H3N 0.2336(12) 0.8080(15) -0.051(2) 0.040(4) Uiso d . 1 . .
H H2N 0.3224(11) 0.6823(14) 0.081(2) 0.038(4) Uiso d . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.3944(19) ?
C1 C2 . 1.3928(19) ?
C1 N1 . 1.4099(16) ?
C2 C3 . 1.386(2) ?
C2 H2 . 0.94 ?
C3 C4 . 1.376(2) ?
C3 H3 . 0.94 ?
C4 C5 . 1.380(2) ?
C4 H4 . 0.94 ?
C5 C6 . 1.384(2) ?
C5 H5 . 0.94 ?
C6 H6 . 0.94 ?
C7 N1 . 1.3054(17) ?
C7 N2 . 1.3571(17) ?
C7 N3 . 1.3724(17) ?
C8 N2 . 1.4583(18) ?
C8 C10 . 1.510(2) ?
C8 C9 . 1.518(2) ?
C8 H8 . 0.99 ?
C9 H9A . 0.97 ?
C9 H9B . 0.97 ?
C9 H9C . 0.97 ?
C10 H10A . 0.97 ?
C10 H10B . 0.97 ?
C10 H10C . 0.97 ?
C11 N3 . 1.4673(17) ?
C11 C12 . 1.512(2) ?
C11 C13 . 1.511(2) ?
C11 H11 . 0.99 ?
C12 H12A . 0.97 ?
C12 H12B . 0.97 ?
C12 H12C . 0.97 ?
C13 H13A . 0.97 ?
C13 H13B . 0.97 ?
C13 H13C . 0.97 ?
N2 H2N . 0.853(17) ?
N3 H3N . 0.862(18) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 118.11(12) ?
C6 C1 N1 . . 122.57(12) ?
C2 C1 N1 . . 119.00(12) ?
C3 C2 C1 . . 120.82(14) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C4 C3 C2 . . 120.50(14) ?
C4 C3 H3 . . 119.8 ?
C2 C3 H3 . . 119.8 ?
C3 C4 C5 . . 119.30(14) ?
C3 C4 H4 . . 120.4 ?
C5 C4 H4 . . 120.4 ?
C4 C5 C6 . . 120.71(15) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C5 C6 C1 . . 120.56(14) ?
C5 C6 H6 . . 119.7 ?
C1 C6 H6 . . 119.7 ?
N1 C7 N2 . . 119.43(12) ?
N1 C7 N3 . . 127.16(12) ?
N2 C7 N3 . . 113.39(11) ?
N2 C8 C10 . . 111.70(12) ?
N2 C8 C9 . . 107.29(12) ?
C10 C8 C9 . . 111.65(13) ?
N2 C8 H8 . . 108.7 ?
C10 C8 H8 . . 108.7 ?
C9 C8 H8 . . 108.7 ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C8 C10 H10A . . 109.5 ?
C8 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C8 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
N3 C11 C12 . . 107.35(12) ?
N3 C11 C13 . . 112.08(12) ?
C12 C11 C13 . . 111.76(13) ?
N3 C11 H11 . . 108.5 ?
C12 C11 H11 . . 108.5 ?
C13 C11 H11 . . 108.5 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C11 C13 H13A . . 109.5 ?
C11 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C11 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C7 N1 C1 . . 122.11(11) ?
C7 N2 C8 . . 125.10(12) ?
C7 N2 H2N . . 116.5(11) ?
C8 N2 H2N . . 115.4(11) ?
C7 N3 C11 . . 124.52(11) ?
C7 N3 H3N . . 112.0(11) ?
C11 N3 H3N . . 112.2(11) ?
