# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_cmpnd_4a
_database_code_depnum_ccdc_archive 'CCDC 1043411'
_audit_update_record             
;
2015-01-13 deposited with the CCDC.
2015-02-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 B N2, C4 H8 O, Cl'
_chemical_formula_sum            'C20 H28 B Cl N2 O'
_chemical_formula_weight         358.70

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   9.2150(2)
_cell_length_b                   13.4773(3)
_cell_length_c                   17.1221(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.697(2)
_cell_angle_gamma                90.00
_cell_volume                     2107.29(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    11619
_cell_measurement_theta_min      1.02
_cell_measurement_theta_max      30.03

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.131
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_special_details           
; 
Compound underwent phase transition upon cooling to 180 K
data collected above transition at 240(2) K 
;

_diffrn_ambient_temperature      240(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_reflns_number            21422
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_sigmaI/netI    0.0629
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.76
_diffrn_reflns_theta_max         29.98
_reflns_number_total             6052
_reflns_number_gt                3359
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_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.
 Some disorder in THF solvate molecule. Disorder refined with 
 fixed Uiso to obtain sof (50:50) then fixed sof and refined a common Uiso 
 for disordered C and O atoms with bond distance restraints. 
;

_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)+(0.0053P)²+1.8095P] 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         6052
_refine_ls_number_parameters     214
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1606
_refine_ls_R_factor_gt           0.0928
_refine_ls_wR_factor_ref         0.1786
_refine_ls_wR_factor_gt          0.1594
_refine_ls_goodness_of_fit_ref   1.276
_refine_ls_restrained_S_all      1.314
_refine_ls_shift/su_max          0.002
_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
Cl1 Cl 0.73920(8) 0.31289(7) 0.36136(5) 0.0615(3) Uani 1 1 d . . .
N1 N 0.0241(3) 0.22197(19) 0.32110(15) 0.0504(6) Uani 1 1 d . . .
H1 H -0.0505 0.2524 0.3363 0.061 Uiso 1 1 calc R . .
B1 B 0.0068(4) 0.1257(3) 0.2700(2) 0.0528(9) Uani 1 1 d . . .
N2 N 0.1777(3) 0.11334(19) 0.26582(15) 0.0487(6) Uani 1 1 d . . .
C10 C 0.1560(3) 0.2534(2) 0.33919(17) 0.0443(7) Uani 1 1 d . . .
C11 C 0.2579(3) 0.1859(2) 0.30587(17) 0.0458(7) Uani 1 1 d . . .
C12 C 0.4089(3) 0.1858(3) 0.3132(2) 0.0579(8) Uani 1 1 d . . .
H12 H 0.4646 0.2356 0.3416 0.069 Uiso 1 1 calc R . .
C13 C 0.4752(4) 0.1093(3) 0.2770(2) 0.0745(11) Uani 1 1 d . . .
H13 H 0.5778 0.1072 0.2803 0.089 Uiso 1 1 calc R . .
C14 C 0.3924(4) 0.0366(3) 0.2363(2) 0.0743(11) Uani 1 1 d . . .
H14 H 0.4380 -0.0150 0.2118 0.089 Uiso 1 1 calc R . .
C15 C 0.2424(4) 0.0397(3) 0.2316(2) 0.0617(9) Uani 1 1 d . . .
H15 H 0.1853 -0.0103 0.2041 0.074 Uiso 1 1 calc R . .
C21 C 0.1995(3) 0.3412(2) 0.38763(17) 0.0459(7) Uani 1 1 d . . .
C22 C 0.3142(3) 0.4015(2) 0.37162(19) 0.0544(8) Uani 1 1 d . . .
H22 H 0.3645 0.3867 0.3287 0.065 Uiso 1 1 calc R . .
C23 C 0.3549(4) 0.4831(3) 0.4186(2) 0.0636(9) Uani 1 1 d . . .
H23 H 0.4316 0.5243 0.4071 0.076 Uiso 1 1 calc R . .
C24 C 0.2834(4) 0.5038(3) 0.4819(2) 0.0664(10) Uani 1 1 d . . .
H24 H 0.3121 0.5586 0.5143 0.080 Uiso 1 1 calc R . .
C25 C 0.1700(4) 0.4448(3) 0.4980(2) 0.0646(10) Uani 1 1 d . . .
H25 H 0.1215 0.4593 0.5416 0.078 Uiso 1 1 calc R . .
C26 C 0.1259(3) 0.3637(3) 0.45071(18) 0.0576(9) Uani 1 1 d . . .
H26 H 0.0466 0.3244 0.4614 0.069 Uiso 1 1 calc R . .
C31 C -0.0520(4) 0.0348(3) 0.3168(2) 0.0751(11) Uani 1 1 d . . .
H31B H -0.1552 0.0469 0.3218 0.090 Uiso 1 1 calc R . .
H31A H -0.0475 -0.0254 0.2851 0.090 Uiso 1 1 calc R . .
C32 C 0.0280(6) 0.0154(4) 0.3973(3) 0.1134(17) Uani 1 1 d . . .
H32C H -0.0149 -0.0415 0.4202 0.170 Uiso 1 1 calc R . .
H32B H 0.0204 0.0731 0.4304 0.170 Uiso 1 1 calc R . .
H32A H 0.1303 0.0022 0.3935 0.170 Uiso 1 1 calc R . .
C33 C -0.0812(4) 0.1455(3) 0.1845(2) 0.0674(10) Uani 1 1 d . . .
H33B H -0.0752 0.0855 0.1528 0.081 Uiso 1 1 calc R . .
H33A H -0.1846 0.1555 0.1903 0.081 Uiso 1 1 calc R . .
C34 C -0.0318(5) 0.2323(4) 0.1392(2) 0.0951(14) Uani 1 1 d . . .
H34C H -0.0886 0.2346 0.0872 0.143 Uiso 1 1 calc R . .
H34B H 0.0711 0.2249 0.1340 0.143 Uiso 1 1 calc R . .
H34A H -0.0462 0.2934 0.1671 0.143 Uiso 1 1 calc R . .
O50A O 0.3891(14) 0.3201(9) 0.1414(7) 0.193(2) Uiso 0.50 1 d PD A 1
C51A C 0.363(2) 0.4035(12) 0.0777(9) 0.193(2) Uiso 0.50 1 d PD A 1
H51A H 0.2618 0.4285 0.0715 0.231 Uiso 0.50 1 calc PR A 1
H51B H 0.4316 0.4587 0.0882 0.231 Uiso 0.50 1 calc PR A 1
C52A C 0.392(2) 0.3443(14) 0.0116(9) 0.193(2) Uiso 0.50 1 d PD A 1
H52A H 0.4107 0.3874 -0.0320 0.231 Uiso 0.50 1 calc PR A 1
H52B H 0.3067 0.3026 -0.0065 0.231 Uiso 0.50 1 calc PR A 1
C53A C 0.520(2) 0.2819(13) 0.0366(10) 0.193(2) Uiso 0.50 1 d PD A 1
H53A H 0.5242 0.2251 0.0013 0.231 Uiso 0.50 1 calc PR A 1
H53B H 0.6110 0.3199 0.0392 0.231 Uiso 0.50 1 calc PR A 1
C54A C 0.4954(19) 0.2549(12) 0.1039(10) 0.193(2) Uiso 0.50 1 d PD A 1
H54A H 0.5887 0.2533 0.1389 0.231 Uiso 0.50 1 calc PR A 1
H54B H 0.4567 0.1871 0.1002 0.231 Uiso 0.50 1 calc PR A 1
O50B O 0.4352(14) 0.3683(9) 0.1587(6) 0.193(2) Uiso 0.50 1 d PD B 2
C51B C 0.3363(17) 0.3528(14) 0.0726(9) 0.193(2) Uiso 0.50 1 d PD B 2
H51C H 0.3033 0.2839 0.0654 0.231 Uiso 0.50 1 calc PR B 2
H51D H 0.2507 0.3966 0.0666 0.231 Uiso 0.50 1 calc PR B 2
C52B C 0.4365(18) 0.3788(15) 0.0171(9) 0.193(2) Uiso 0.50 1 d PD B 2
H52C H 0.4137 0.3412 -0.0321 0.231 Uiso 0.50 1 calc PR B 2
H52D H 0.4310 0.4498 0.0049 0.231 Uiso 0.50 1 calc PR B 2
C53B C 0.5789(18) 0.3529(14) 0.0564(10) 0.193(2) Uiso 0.50 1 d PD B 2
H53C H 0.6230 0.3023 0.0260 0.231 Uiso 0.50 1 calc PR B 2
H53D H 0.6424 0.4115 0.0605 0.231 Uiso 0.50 1 calc PR B 2
C54B C 0.5667(17) 0.3177(14) 0.1295(10) 0.193(2) Uiso 0.50 1 d PD B 2
H54C H 0.6562 0.3321 0.1654 0.231 Uiso 0.50 1 calc PR B 2
H54D H 0.5524 0.2457 0.1276 0.231 Uiso 0.50 1 calc PR B 2


_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 C10 1.285(3) . ?
N1 B1 1.561(4) . ?
N1 H1 0.8700 . ?
B1 C31 1.597(5) . ?
B1 N2 1.595(4) . ?
B1 C33 1.598(5) . ?
N2 C15 1.334(4) . ?
N2 C11 1.356(4) . ?
C10 C21 1.470(4) . ?
C10 C11 1.476(4) . ?
C11 C12 1.380(4) . ?
C12 C13 1.386(5) . ?
C12 H12 0.9400 . ?
C13 C14 1.373(5) . ?
C13 H13 0.9400 . ?
C14 C15 1.374(5) . ?
C14 H14 0.9400 . ?
C15 H15 0.9400 . ?
C21 C26 1.384(4) . ?
C21 C22 1.390(4) . ?
C22 C23 1.385(4) . ?
C22 H22 0.9400 . ?
C23 C24 1.371(5) . ?
C23 H23 0.9400 . ?
C24 C25 1.371(5) . ?
C24 H24 0.9400 . ?
C25 C26 1.389(5) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?
C31 C32 1.496(6) . ?
C31 H31B 0.9800 . ?
C31 H31A 0.9800 . ?
C32 H32C 0.9700 . ?
C32 H32B 0.9700 . ?
C32 H32A 0.9700 . ?
C33 C34 1.508(5) . ?
C33 H33B 0.9800 . ?
C33 H33A 0.9800 . ?
C34 H34C 0.9700 . ?
C34 H34B 0.9700 . ?
C34 H34A 0.9700 . ?
O50A C54A 1.520(12) . ?
O50A C51A 1.563(12) . ?
C51A C52A 1.438(13) . ?
C51A H51A 0.9800 . ?
C51A H51B 0.9800 . ?
C52A C53A 1.466(15) . ?
C52A H52A 0.9800 . ?
C52A H52B 0.9800 . ?
C53A C54A 1.258(13) . ?
C53A H53A 0.9800 . ?
C53A H53B 0.9800 . ?
C54A H54A 0.9800 . ?
C54A H54B 0.9800 . ?
O50B C54B 1.532(12) . ?
O50B C51B 1.640(12) . ?
C51B C52B 1.454(13) . ?
C51B H51C 0.9800 . ?
C51B H51D 0.9800 . ?
C52B C53B 1.435(14) . ?
C52B H52C 0.9800 . ?
C52B H52D 0.9800 . ?
C53B C54B 1.357(13) . ?
C53B H53C 0.9800 . ?
C53B H53D 0.9800 . ?
C54B H54C 0.9800 . ?
C54B H54D 0.9800 . ?

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
C10 N1 B1 115.6(2) . . ?
C10 N1 H1 122.2 . . ?
B1 N1 H1 122.2 . . ?
N1 B1 C31 111.9(3) . . ?
N1 B1 N2 94.8(2) . . ?
C31 B1 N2 110.3(3) . . ?
N1 B1 C33 112.0(3) . . ?
C31 B1 C33 115.1(3) . . ?
N2 B1 C33 111.0(3) . . ?
C15 N2 C11 120.9(3) . . ?
C15 N2 B1 126.9(3) . . ?
C11 N2 B1 112.2(2) . . ?
N1 C10 C21 125.4(3) . . ?
N1 C10 C11 109.5(3) . . ?
C21 C10 C11 125.1(2) . . ?
N2 C11 C12 121.3(3) . . ?
N2 C11 C10 107.9(2) . . ?
C12 C11 C10 130.7(3) . . ?
C11 C12 C13 117.4(3) . . ?
C11 C12 H12 121.3 . . ?
C13 C12 H12 121.3 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
N2 C15 C14 120.1(3) . . ?
N2 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C26 C21 C22 119.4(3) . . ?
C26 C21 C10 119.4(3) . . ?
C22 C21 C10 121.1(3) . . ?
C23 C22 C21 120.2(3) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 120.0(3) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.1(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C26 120.7(3) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C21 C26 C25 119.5(3) . . ?
C21 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C32 C31 B1 116.0(3) . . ?
C32 C31 H31B 108.3 . . ?
B1 C31 H31B 108.3 . . ?
C32 C31 H31A 108.3 . . ?
B1 C31 H31A 108.3 . . ?
H31B C31 H31A 107.4 . . ?
C31 C32 H32C 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32C C32 H32B 109.5 . . ?
C31 C32 H32A 109.5 . . ?
H32C C32 H32A 109.5 . . ?
H32B C32 H32A 109.5 . . ?
C34 C33 B1 116.8(3) . . ?
C34 C33 H33B 108.1 . . ?
B1 C33 H33B 108.1 . . ?
C34 C33 H33A 108.1 . . ?
B1 C33 H33A 108.1 . . ?
H33B C33 H33A 107.3 . . ?
C33 C34 H34C 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34C C34 H34B 109.5 . . ?
C33 C34 H34A 109.5 . . ?
H34C C34 H34A 109.5 . . ?
H34B C34 H34A 109.5 . . ?
C54A O50A C51A 99.8(10) . . ?
C52A C51A O50A 97.0(11) . . ?
C52A C51A H51A 112.4 . . ?
O50A C51A H51A 112.4 . . ?
C52A C51A H51B 112.4 . . ?
O50A C51A H51B 112.4 . . ?
H51A C51A H51B 109.9 . . ?
C51A C52A C53A 108.5(13) . . ?
C51A C52A H52A 110.0 . . ?
C53A C52A H52A 110.0 . . ?
C51A C52A H52B 110.0 . . ?
C53A C52A H52B 110.0 . . ?
H52A C52A H52B 108.4 . . ?
C54A C53A C52A 101.4(14) . . ?
C54A C53A H53A 111.5 . . ?
C52A C53A H53A 111.5 . . ?
C54A C53A H53B 111.5 . . ?
C52A C53A H53B 111.5 . . ?
H53A C53A H53B 109.3 . . ?
C53A C54A O50A 115.1(13) . . ?
C53A C54A H54A 108.5 . . ?
O50A C54A H54A 108.5 . . ?
C53A C54A H54B 108.5 . . ?
O50A C54A H54B 108.5 . . ?
H54A C54A H54B 107.5 . . ?
C54B O50B C51B 91.0(10) . . ?
C52B C51B O50B 103.4(11) . . ?
C52B C51B H51C 111.1 . . ?
O50B C51B H51C 111.1 . . ?
C52B C51B H51D 111.1 . . ?
O50B C51B H51D 111.1 . . ?
H51C C51B H51D 109.0 . . ?
C53B C52B C51B 104.8(13) . . ?
C53B C52B H52C 110.8 . . ?
C51B C52B H52C 110.8 . . ?
C53B C52B H52D 110.8 . . ?
C51B C52B H52D 110.8 . . ?
H52C C52B H52D 108.9 . . ?
C54B C53B C52B 109.5(13) . . ?
C54B C53B H53C 109.8 . . ?
C52B C53B H53C 109.8 . . ?
C54B C53B H53D 109.8 . . ?
C52B C53B H53D 109.8 . . ?
H53C C53B H53D 108.2 . . ?
C53B C54B O50B 108.2(13) . . ?
C53B C54B H54C 110.1 . . ?
O50B C54B H54C 110.1 . . ?
C53B C54B H54D 110.1 . . ?
O50B C54B H54D 110.1 . . ?
H54C C54B H54D 108.4 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        29.98
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_cmpnd_4b
_database_code_depnum_ccdc_archive 'CCDC 1043412'
_audit_update_record             
;
2015-01-13 deposited with the CCDC.
2015-02-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 B2 F5 N2'
_chemical_formula_sum            'C12 H9 B2 F5 N2'
_chemical_formula_weight         297.83

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca
_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.934(3)
_cell_length_b                   12.290(4)
_cell_length_c                   21.001(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2564.0(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6665
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      27.82

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9655
_exptl_absorpt_correction_T_max  0.9791
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
Saint Plus, Bruker AXS, Madison, WI, USA.  
;

_diffrn_ambient_temperature      173(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_reflns_number            25423
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         27.88
_reflns_number_total             2957
_reflns_number_gt                2480
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT, v6.45a'
_computing_data_reduction        'Bruker SHELXTL XPREP'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury v2.3'
_computing_publication_material  'Bruker SHELXTL XCIF'

_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. 
 Structure solved by direct methods to reveal all non-H atoms. H atoms 
 added at calculated positions using a riding model and all non-H atoms
 refined anisotropically in latter stages of refinment.
;

_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)+(0.0792P)²+0.9442P] 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         2957
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1389
_refine_ls_wR_factor_gt          0.1307
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.95396(18) 0.15281(15) 0.94754(8) 0.0272(4) Uani 1 1 d . . .
B2 B 1.18440(18) 0.06977(16) 0.89253(9) 0.0321(4) Uani 1 1 d . . .
C10 C 0.93851(14) 0.00635(11) 0.87435(7) 0.0229(3) Uani 1 1 d . . .
F11 F 0.96545(11) 0.25734(8) 0.92610(5) 0.0373(3) Uani 1 1 d . . .
N11 N 0.80210(13) 0.11309(11) 0.93741(6) 0.0267(3) Uani 1 1 d . . .
C11 C 0.79824(15) 0.03043(12) 0.89518(7) 0.0260(3) Uani 1 1 d . . .
F12 F 0.99393(9) 0.14145(8) 1.00933(4) 0.0346(3) Uani 1 1 d . . .
N12 N 1.02461(12) 0.06848(10) 0.90209(6) 0.0243(3) Uani 1 1 d . . .
C12 C 0.67957(17) -0.01955(14) 0.87902(9) 0.0351(4) Uani 1 1 d . . .
H12 H 0.6790 -0.0794 0.8504 0.036(5) Uiso 1 1 calc R . .
C13 C 0.56138(17) 0.02071(16) 0.90614(10) 0.0414(4) Uani 1 1 d . . .
H13 H 0.4772 -0.0114 0.8957 0.055(7) Uiso 1 1 calc R . .
C14 C 0.56677(18) 0.10685(16) 0.94795(9) 0.0401(4) Uani 1 1 d . . .
H14 H 0.4862 0.1354 0.9657 0.060(7) Uiso 1 1 calc R . .
C15 C 0.68972(17) 0.15171(14) 0.96409(9) 0.0337(4) Uani 1 1 d . . .
H15 H 0.6943 0.2096 0.9940 0.035(5) Uiso 1 1 calc R . .
F21 F 1.23895(11) -0.01485(12) 0.92687(7) 0.0604(4) Uani 1 1 d . . .
C21 C 0.96406(15) -0.07917(12) 0.82653(7) 0.0248(3) Uani 1 1 d . . .
F22 F 1.22888(11) 0.16831(10) 0.91557(6) 0.0507(3) Uani 1 1 d . . .
C22 C 0.89359(17) -0.07564(14) 0.76899(8) 0.0326(4) Uani 1 1 d . . .
H22 H 0.8316 -0.0184 0.7610 0.039 Uiso 1 1 calc R . .
F23 F 1.21234(11) 0.05950(9) 0.82913(5) 0.0451(3) Uani 1 1 d . . .
C23 C 0.91400(18) -0.15533(15) 0.72380(8) 0.0385(4) Uani 1 1 d . . .
H23 H 0.8679 -0.1521 0.6842 0.046 Uiso 1 1 calc R . .
C24 C 1.0015(2) -0.23963(16) 0.73631(9) 0.0433(4) Uani 1 1 d . . .
H24 H 1.0145 -0.2951 0.7054 0.056(6) Uiso 1 1 calc R . .
C25 C 1.0705(2) -0.24417(15) 0.79341(9) 0.0428(4) Uani 1 1 d . . .
H25 H 1.1301 -0.3029 0.8016 0.056(6) Uiso 1 1 calc R . .
C26 C 1.05316(17) -0.16350(14) 0.83867(8) 0.0322(4) Uani 1 1 d . . .
H26 H 1.1017 -0.1659 0.8776 0.038(5) 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 F12 1.364(2) . ?
B1 F11 1.366(2) . ?
B1 N12 1.574(2) . ?
B1 N11 1.600(2) . ?
B2 F23 1.366(2) . ?
B2 F21 1.377(2) . ?
B2 F22 1.377(2) . ?
B2 N12 1.600(2) . ?
C10 N12 1.2861(19) . ?
C10 C21 1.476(2) . ?
C10 C11 1.490(2) . ?
N11 C15 1.336(2) . ?
N11 C11 1.349(2) . ?
C11 C12 1.372(2) . ?
C12 C13 1.396(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C21 C26 1.387(2) . ?
C21 C22 1.397(2) . ?
C22 C23 1.379(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.377(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.383(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.384(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F12 B1 F11 112.67(14) . . ?
F12 B1 N12 112.31(14) . . ?
F11 B1 N12 112.46(13) . . ?
F12 B1 N11 111.70(13) . . ?
F11 B1 N11 108.78(14) . . ?
N12 B1 N11 97.98(12) . . ?
F23 B2 F21 111.16(15) . . ?
F23 B2 F22 111.01(15) . . ?
F21 B2 F22 110.73(16) . . ?
F23 B2 N12 108.85(14) . . ?
F21 B2 N12 108.50(14) . . ?
F22 B2 N12 106.44(14) . . ?
N12 C10 C21 128.08(14) . . ?
N12 C10 C11 111.78(13) . . ?
C21 C10 C11 120.14(13) . . ?
C15 N11 C11 121.30(14) . . ?
C15 N11 B1 128.58(13) . . ?
C11 N11 B1 110.12(12) . . ?
N11 C11 C12 121.61(14) . . ?
N11 C11 C10 108.42(12) . . ?
C12 C11 C10 129.93(14) . . ?
C10 N12 B1 111.66(13) . . ?
C10 N12 B2 127.50(13) . . ?
B1 N12 B2 120.79(12) . . ?
C11 C12 C13 117.59(16) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 H12 121.2 . . ?
C14 C13 C12 120.02(16) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 119.84(16) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
N11 C15 C14 119.58(16) . . ?
N11 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C26 C21 C22 120.13(14) . . ?
C26 C21 C10 121.14(14) . . ?
C22 C21 C10 118.70(14) . . ?
C23 C22 C21 119.97(15) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 C23 C22 119.72(16) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 120.58(16) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C26 120.33(16) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 119.25(16) . . ?
C25 C26 H26 120.4 . . ?
C21 C26 H26 120.4 . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        27.88
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_cmpnd_4c
_database_code_depnum_ccdc_archive 'CCDC 1043413'
_audit_update_record             
;
2015-01-13 deposited with the CCDC.
2015-02-16 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_STRVA01_cmpnd_4c            
;
PROBLEM: Flack test results are ambiguous.
RESPONSE: The structure has Z' = 2 with a non-crystallographic
inversion centre between the two independent molecules (which differ
in the conformation of the Et groups attached to the B centre). In this
context absolute structure determination is not meaningful.
;
# end Validation Reply Form 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H19 B N3,C4 H8 O, Cl'
_chemical_formula_sum            'C19 H27 B Cl N3 O'
_chemical_formula_weight         359.71

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   9.38350(10)
_cell_length_b                   12.8596(3)
_cell_length_c                   16.6196(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.1807(12)
_cell_angle_gamma                90.00
_cell_volume                     1979.77(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    22890
_cell_measurement_theta_min      1.02
_cell_measurement_theta_max      29.13

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;


_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_reflns_number            25481
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0502
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         26.37
_reflns_number_total             7194
_reflns_number_gt                6037
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SHELXS (Sheldrick)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'


_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)+(0.0379P)²+1.0161P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.54(6)
_refine_ls_number_reflns         7194
_refine_ls_number_parameters     453
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.0973
_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
Cl1 Cl 0.26709(7) 0.62682(6) 0.11842(5) 0.0358(2) Uani 1 1 d . . .
Cl2 Cl 0.71587(7) 0.22436(6) 0.37826(5) 0.03328(19) Uani 1 1 d . . .
N1 N 0.4370(2) 0.1255(2) 0.41617(14) 0.0257(5) Uani 1 1 d . . .
H1B H 0.5138 0.1519 0.3994 0.031 Uiso 1 1 calc R . .
C1 C 0.2028(3) -0.0513(3) 0.50635(19) 0.0299(7) Uani 1 1 d . . .
H1A H 0.2525 -0.1107 0.5304 0.036 Uiso 1 1 calc R . .
B1 B 0.4420(3) 0.0211(3) 0.4646(2) 0.0263(7) Uani 1 1 d . . .
N2 N 0.2743(2) 0.0224(2) 0.47273(14) 0.0246(6) Uani 1 1 d . . .
C2 C 0.0549(3) -0.0406(3) 0.50606(19) 0.0325(8) Uani 1 1 d . . .
H2A H 0.0028 -0.0933 0.5290 0.039 Uiso 1 1 calc R . .
C3 C -0.0151(3) 0.0470(3) 0.47214(18) 0.0311(7) Uani 1 1 d . . .
H3A H -0.1156 0.0551 0.4724 0.037 Uiso 1 1 calc R . .
C4 C 0.0604(3) 0.1238(3) 0.43758(17) 0.0280(7) Uani 1 1 d . . .
H4A H 0.0134 0.1847 0.4144 0.034 Uiso 1 1 calc R . .
C5 C 0.2055(3) 0.1082(3) 0.43818(16) 0.0231(6) Uani 1 1 d . . .
C6 C 0.3130(3) 0.1703(3) 0.40248(18) 0.0239(7) Uani 1 1 d . . .
C7 C 0.2804(3) 0.2665(2) 0.35471(18) 0.0246(7) Uani 1 1 d . . .
C10 C 0.2126(3) 0.4427(3) 0.26716(19) 0.0350(8) Uani 1 1 d . . .
H10A H 0.1859 0.5050 0.2378 0.042 Uiso 1 1 calc R . .
C12 C 0.6334(3) -0.0910(3) 0.4008(2) 0.0400(7) Uani 1 1 d . . .
H12A H 0.6435 -0.1521 0.3669 0.060 Uiso 1 1 calc R . .
H12B H 0.6914 -0.1008 0.4548 0.060 Uiso 1 1 calc R . .
H12C H 0.6669 -0.0290 0.3751 0.060 Uiso 1 1 calc R . .
C13 C 0.4734(3) -0.0772(3) 0.4098(2) 0.0348(8) Uani 1 1 d . . .
H13A H 0.4400 -0.1411 0.4343 0.042 Uiso 1 1 calc R . .
H13B H 0.4157 -0.0693 0.3548 0.042 Uiso 1 1 calc R . .
C14 C 0.5404(3) 0.0301(3) 0.55279(19) 0.0314(7) Uani 1 1 d . . .
H14A H 0.5313 -0.0355 0.5828 0.038 Uiso 1 1 calc R . .
H14B H 0.6424 0.0365 0.5450 0.038 Uiso 1 1 calc R . .
C15 C 0.5055(4) 0.1205(3) 0.6059(2) 0.0438(8) Uani 1 1 d . . .
H15A H 0.5712 0.1189 0.6581 0.066 Uiso 1 1 calc R . .
H15B H 0.4057 0.1142 0.6158 0.066 Uiso 1 1 calc R . .
H15C H 0.5173 0.1863 0.5781 0.066 Uiso 1 1 calc R . .
C11 C 0.1455(3) 0.4137(3) 0.33143(19) 0.0322(8) Uani 1 1 d . . .
H11A H 0.0729 0.4583 0.3458 0.039 Uiso 1 1 calc R . .
C9 C 0.3192(3) 0.3796(3) 0.24636(19) 0.0349(8) Uani 1 1 d . . .
H9A H 0.3668 0.3973 0.2019 0.042 Uiso 1 1 calc R . .
C8 C 0.3566(3) 0.2894(3) 0.29131(18) 0.0281(7) Uani 1 1 d . . .
H8A H 0.4313 0.2450 0.2792 0.034 Uiso 1 1 calc R . .
N3 N 0.1757(2) 0.3265(2) 0.37531(15) 0.0267(6) Uani 1 1 d . . .
B100 B 0.5380(4) 0.8222(3) 0.0371(2) 0.0301(8) Uani 1 1 d . . .
N101 N 0.5505(2) 0.7182(2) 0.08499(14) 0.0271(6) Uani 1 1 d . . .
H10H H 0.4752 0.6881 0.1005 0.032 Uiso 1 1 calc R . .
C101 C 0.7734(3) 0.9035(3) -0.00478(19) 0.0335(7) Uani 1 1 d . . .
H10B H 0.7195 0.9601 -0.0308 0.040 Uiso 1 1 calc R . .
N102 N 0.7055(3) 0.8283(2) 0.03009(14) 0.0272(6) Uani 1 1 d . . .
C102 C 0.9203(3) 0.8997(3) -0.00330(19) 0.0353(8) Uani 1 1 d . . .
H10C H 0.9678 0.9528 -0.0287 0.042 Uiso 1 1 calc R . .
C103 C 0.9984(3) 0.8175(3) 0.03561(19) 0.0351(8) Uani 1 1 d . . .
H10D H 1.1001 0.8149 0.0376 0.042 Uiso 1 1 calc R . .
C104 C 0.9291(3) 0.7389(3) 0.07165(17) 0.0290(7) Uani 1 1 d . . .
H10E H 0.9815 0.6821 0.0983 0.035 Uiso 1 1 calc R . .
C105 C 0.7812(3) 0.7463(3) 0.06732(17) 0.0259(7) Uani 1 1 d . . .
C106 C 0.6781(3) 0.6788(3) 0.10066(17) 0.0257(7) Uani 1 1 d . . .
C107 C 0.7145(3) 0.5812(2) 0.14598(17) 0.0243(7) Uani 1 1 d . . .
C110 C 0.7918(3) 0.4039(3) 0.22915(18) 0.0313(7) Uani 1 1 d . . .
H11B H 0.8219 0.3415 0.2575 0.038 Uiso 1 1 calc R . .
C112 C 0.4657(4) 0.7191(4) -0.1030(2) 0.0506(10) Uani 1 1 d . . .
H11C H 0.3989 0.7218 -0.1547 0.076 Uiso 1 1 calc R . .
H11D H 0.4500 0.6547 -0.0742 0.076 Uiso 1 1 calc R . .
H11E H 0.5653 0.7211 -0.1138 0.076 Uiso 1 1 calc R . .
C113 C 0.4392(3) 0.8115(3) -0.0509(2) 0.0359(8) Uani 1 1 d . . .
H11F H 0.3370 0.8093 -0.0427 0.043 Uiso 1 1 calc R . .
H11N H 0.4517 0.8755 -0.0822 0.043 Uiso 1 1 calc R . .
C114 C 0.4904(3) 0.9164(3) 0.09070(19) 0.0374(8) Uani 1 1 d . . .
H11G H 0.4866 0.9806 0.0575 0.045 Uiso 1 1 calc R . .
H11H H 0.3912 0.9024 0.1010 0.045 Uiso 1 1 calc R . .
C115 C 0.5853(4) 0.9380(3) 0.1727(2) 0.0589(10) Uani 1 1 d . . .
H11I H 0.5959 0.8741 0.2053 0.088 Uiso 1 1 calc R . .
H11J H 0.5401 0.9919 0.2019 0.088 Uiso 1 1 calc R . .
H11K H 0.6806 0.9619 0.1635 0.088 Uiso 1 1 calc R . .
C109 C 0.6784(3) 0.4609(3) 0.24948(18) 0.0302(7) Uani 1 1 d . . .
H10F H 0.6292 0.4387 0.2922 0.036 Uiso 1 1 calc R . .
C111 C 0.8612(3) 0.4389(3) 0.16680(18) 0.0307(7) Uani 1 1 d . . .
H11M H 0.9378 0.3981 0.1525 0.037 Uiso 1 1 calc R . .
C108 C 0.6379(3) 0.5504(3) 0.20671(18) 0.0294(7) Uani 1 1 d . . .
H10G H 0.5588 0.5905 0.2185 0.035 Uiso 1 1 calc R . .
N103 N 0.8264(2) 0.5269(2) 0.12553(15) 0.0288(6) Uani 1 1 d . . .
O1 O 0.1363(3) 0.2541(2) 0.73321(16) 0.0558(7) Uani 1 1 d . . .
C4S C 0.0472(4) 0.3441(3) 0.7281(2) 0.0514(9) Uani 1 1 d . . .
H4SA H 0.0771 0.3949 0.6893 0.062 Uiso 1 1 calc R . .
H4SB H 0.0535 0.3776 0.7822 0.062 Uiso 1 1 calc R . .
C3S C -0.1023(4) 0.3068(3) 0.6991(2) 0.0555(10) Uani 1 1 d . . .
H3SA H -0.1620 0.3622 0.6691 0.067 Uiso 1 1 calc R . .
H3SB H -0.1491 0.2830 0.7451 0.067 Uiso 1 1 calc R . .
C1S C 0.0732(5) 0.1878(4) 0.6690(3) 0.0861(16) Uani 1 1 d . . .
H1SA H 0.0796 0.1146 0.6877 0.103 Uiso 1 1 calc R . .
H1SB H 0.1263 0.1942 0.6223 0.103 Uiso 1 1 calc R . .
C2S C -0.0806(4) 0.2168(4) 0.6429(3) 0.0648(12) Uani 1 1 d . . .
H2SA H -0.1455 0.1580 0.6502 0.078 Uiso 1 1 calc R . .
H2SB H -0.0983 0.2388 0.5851 0.078 Uiso 1 1 calc R . .
O2 O 1.1168(3) 1.0738(2) 0.25707(13) 0.0485(7) Uani 1 1 d . . .
C22S C 0.9690(4) 1.1260(4) 0.1360(2) 0.0599(11) Uani 1 1 d . . .
H22A H 0.9230 1.1897 0.1103 0.072 Uiso 1 1 calc R . .
H22B H 0.9095 1.0648 0.1161 0.072 Uiso 1 1 calc R . .
C23S C 1.1246(4) 1.1144(3) 0.1195(2) 0.0560(10) Uani 1 1 d . . .
H23A H 1.1277 1.0777 0.0675 0.067 Uiso 1 1 calc R . .
H23B H 1.1723 1.1829 0.1183 0.067 Uiso 1 1 calc R . .
C24S C 1.1934(4) 1.0504(3) 0.1914(2) 0.0509(9) Uani 1 1 d . . .
H24A H 1.1859 0.9754 0.1781 0.061 Uiso 1 1 calc R . .
H24B H 1.2967 1.0687 0.2064 0.061 Uiso 1 1 calc R . .
C21S C 0.9907(4) 1.1331(4) 0.2266(2) 0.0608(10) Uani 1 1 d . . .
H21A H 1.0040 1.2065 0.2441 0.073 Uiso 1 1 calc R . .
H21B H 0.9057 1.1048 0.2476 0.073 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 C6 1.286(3) . ?
N1 B1 1.563(5) . ?
N1 H1B 0.8800 . ?
C1 N2 1.334(4) . ?
C1 C2 1.394(4) . ?
C1 H1A 0.9500 . ?
B1 N2 1.600(4) . ?
B1 C14 1.607(4) . ?
B1 C13 1.613(5) . ?
N2 C5 1.359(4) . ?
C2 C3 1.379(5) . ?
C2 H2A 0.9500 . ?
C3 C4 1.391(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.374(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.482(4) . ?
C6 C7 1.475(4) . ?
C7 N3 1.336(4) . ?
C7 C8 1.396(4) . ?
C10 C9 1.375(5) . ?
C10 C11 1.375(4) . ?
C10 H10A 0.9500 . ?
C12 C13 1.543(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.526(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C11 N3 1.343(4) . ?
C11 H11A 0.9500 . ?
C9 C8 1.395(5) . ?
C9 H9A 0.9500 . ?
C8 H8A 0.9500 . ?
B100 N101 1.550(5) . ?
B100 N102 1.597(4) . ?
B100 C113 1.608(5) . ?
B100 C114 1.609(5) . ?
N101 C106 1.288(4) . ?
N101 H10H 0.8800 . ?
C101 N102 1.340(4) . ?
C101 C102 1.376(4) . ?
C101 H10B 0.9500 . ?
N102 C105 1.364(4) . ?
C102 C103 1.386(5) . ?
C102 H10C 0.9500 . ?
C103 C104 1.389(5) . ?
C103 H10D 0.9500 . ?
C104 C105 1.381(4) . ?
C104 H10E 0.9500 . ?
C105 C106 1.472(4) . ?
C106 C107 1.475(4) . ?
C107 N103 1.349(4) . ?
C107 C108 1.387(4) . ?
C110 C109 1.378(4) . ?
C110 C111 1.384(4) . ?
C110 H11B 0.9500 . ?
C112 C113 1.514(5) . ?
C112 H11C 0.9800 . ?
C112 H11D 0.9800 . ?
C112 H11E 0.9800 . ?
C113 H11F 0.9900 . ?
C113 H11N 0.9900 . ?
C114 C115 1.530(5) . ?
C114 H11G 0.9900 . ?
C114 H11H 0.9900 . ?
C115 H11I 0.9800 . ?
C115 H11J 0.9800 . ?
C115 H11K 0.9800 . ?
C109 C108 1.374(5) . ?
C109 H10F 0.9500 . ?
C111 N103 1.337(4) . ?
C111 H11M 0.9500 . ?
C108 H10G 0.9500 . ?
O1 C1S 1.420(5) . ?
O1 C4S 1.421(4) . ?
C4S C3S 1.489(5) . ?
C4S H4SA 0.9900 . ?
C4S H4SB 0.9900 . ?
C3S C2S 1.521(6) . ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C1S C2S 1.487(5) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
C2S H2SA 0.9900 . ?
C2S H2SB 0.9900 . ?
O2 C21S 1.431(4) . ?
O2 C24S 1.431(4) . ?
C22S C21S 1.490(5) . ?
C22S C23S 1.535(5) . ?
C22S H22A 0.9900 . ?
C22S H22B 0.9900 . ?
C23S C24S 1.508(5) . ?
C23S H23A 0.9900 . ?
C23S H23B 0.9900 . ?
C24S H24A 0.9900 . ?
C24S H24B 0.9900 . ?
C21S H21A 0.9900 . ?
C21S H21B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 B1 115.3(2) . . ?
C6 N1 H1B 122.3 . . ?
B1 N1 H1B 122.3 . . ?
N2 C1 C2 119.7(3) . . ?
N2 C1 H1A 120.1 . . ?
C2 C1 H1A 120.1 . . ?
N1 B1 N2 94.9(2) . . ?
N1 B1 C14 111.9(3) . . ?
N2 B1 C14 110.6(2) . . ?
N1 B1 C13 112.0(3) . . ?
N2 B1 C13 109.1(3) . . ?
C14 B1 C13 116.2(3) . . ?
C1 N2 C5 121.1(2) . . ?
C1 N2 B1 126.5(3) . . ?
C5 N2 B1 112.4(2) . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C5 C4 C3 117.6(3) . . ?
C5 C4 H4A 121.2 . . ?
C3 C4 H4A 121.2 . . ?
N2 C5 C4 121.6(3) . . ?
N2 C5 C6 107.4(2) . . ?
C4 C5 C6 130.9(3) . . ?
N1 C6 C7 125.1(3) . . ?
N1 C6 C5 110.0(3) . . ?
C7 C6 C5 124.8(2) . . ?
N3 C7 C8 123.9(3) . . ?
N3 C7 C6 116.3(3) . . ?
C8 C7 C6 119.7(3) . . ?
C9 C10 C11 118.4(3) . . ?
C9 C10 H10A 120.8 . . ?
C11 C10 H10A 120.8 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C12 C13 B1 114.4(3) . . ?
C12 C13 H13A 108.7 . . ?
B1 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
B1 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 B1 116.0(3) . . ?
C15 C14 H14A 108.3 . . ?
B1 C14 H14A 108.3 . . ?
C15 C14 H14B 108.3 . . ?
B1 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C11 C10 124.5(3) . . ?
N3 C11 H11A 117.8 . . ?
C10 C11 H11A 117.8 . . ?
C10 C9 C8 119.2(3) . . ?
C10 C9 H9A 120.4 . . ?
C8 C9 H9A 120.4 . . ?
C9 C8 C7 117.7(3) . . ?
C9 C8 H8A 121.2 . . ?
C7 C8 H8A 121.2 . . ?
C7 N3 C11 116.3(3) . . ?
N101 B100 N102 94.9(2) . . ?
N101 B100 C113 112.3(3) . . ?
N102 B100 C113 111.7(2) . . ?
N101 B100 C114 111.8(3) . . ?
N102 B100 C114 111.5(3) . . ?
C113 B100 C114 113.4(3) . . ?
C106 N101 B100 115.8(2) . . ?
C106 N101 H10H 122.1 . . ?
B100 N101 H10H 122.1 . . ?
N102 C101 C102 120.7(3) . . ?
N102 C101 H10B 119.6 . . ?
C102 C101 H10B 119.6 . . ?
C101 N102 C105 120.4(3) . . ?
C101 N102 B100 127.5(3) . . ?
C105 N102 B100 112.1(2) . . ?
C101 C102 C103 119.3(3) . . ?
C101 C102 H10C 120.3 . . ?
C103 C102 H10C 120.3 . . ?
C102 C103 C104 120.5(3) . . ?
C102 C103 H10D 119.8 . . ?
C104 C103 H10D 119.8 . . ?
C105 C104 C103 117.6(3) . . ?
C105 C104 H10E 121.2 . . ?
C103 C104 H10E 121.2 . . ?
N102 C105 C104 121.5(3) . . ?
N102 C105 C106 107.5(2) . . ?
C104 C105 C106 130.9(3) . . ?
N101 C106 C105 109.7(3) . . ?
N101 C106 C107 124.8(3) . . ?
C105 C106 C107 125.5(3) . . ?
N103 C107 C108 123.4(3) . . ?
N103 C107 C106 115.9(3) . . ?
C108 C107 C106 120.7(3) . . ?
C109 C110 C111 119.0(3) . . ?
C109 C110 H11B 120.5 . . ?
C111 C110 H11B 120.5 . . ?
C113 C112 H11C 109.5 . . ?
C113 C112 H11D 109.5 . . ?
H11C C112 H11D 109.5 . . ?
C113 C112 H11E 109.5 . . ?
H11C C112 H11E 109.5 . . ?
H11D C112 H11E 109.5 . . ?
C112 C113 B100 117.6(3) . . ?
C112 C113 H11F 107.9 . . ?
B100 C113 H11F 107.9 . . ?
C112 C113 H11N 107.9 . . ?
B100 C113 H11N 107.9 . . ?
H11F C113 H11N 107.2 . . ?
C115 C114 B100 117.2(3) . . ?
C115 C114 H11G 108.0 . . ?
B100 C114 H11G 108.0 . . ?
C115 C114 H11H 108.0 . . ?
B100 C114 H11H 108.0 . . ?
H11G C114 H11H 107.2 . . ?
C114 C115 H11I 109.5 . . ?
C114 C115 H11J 109.5 . . ?
H11I C115 H11J 109.5 . . ?
C114 C115 H11K 109.5 . . ?
H11I C115 H11K 109.5 . . ?
H11J C115 H11K 109.5 . . ?
C108 C109 C110 118.6(3) . . ?
C108 C109 H10F 120.7 . . ?
C110 C109 H10F 120.7 . . ?
N103 C111 C110 123.6(3) . . ?
N103 C111 H11M 118.2 . . ?
C110 C111 H11M 118.2 . . ?
C109 C108 C107 118.9(3) . . ?
C109 C108 H10G 120.5 . . ?
C107 C108 H10G 120.5 . . ?
C111 N103 C107 116.4(3) . . ?
C1S O1 C4S 105.9(3) . . ?
O1 C4S C3S 105.8(3) . . ?
O1 C4S H4SA 110.6 . . ?
C3S C4S H4SA 110.6 . . ?
O1 C4S H4SB 110.6 . . ?
C3S C4S H4SB 110.6 . . ?
H4SA C4S H4SB 108.7 . . ?
C4S C3S C2S 103.4(3) . . ?
C4S C3S H3SA 111.1 . . ?
C2S C3S H3SA 111.1 . . ?
C4S C3S H3SB 111.1 . . ?
C2S C3S H3SB 111.1 . . ?
H3SA C3S H3SB 109.0 . . ?
O1 C1S C2S 109.8(3) . . ?
O1 C1S H1SA 109.7 . . ?
C2S C1S H1SA 109.7 . . ?
O1 C1S H1SB 109.7 . . ?
C2S C1S H1SB 109.7 . . ?
H1SA C1S H1SB 108.2 . . ?
C1S C2S C3S 103.3(3) . . ?
C1S C2S H2SA 111.1 . . ?
C3S C2S H2SA 111.1 . . ?
C1S C2S H2SB 111.1 . . ?
C3S C2S H2SB 111.1 . . ?
H2SA C2S H2SB 109.1 . . ?
C21S O2 C24S 109.2(3) . . ?
C21S C22S C23S 101.8(3) . . ?
C21S C22S H22A 111.4 . . ?
C23S C22S H22A 111.4 . . ?
C21S C22S H22B 111.4 . . ?
C23S C22S H22B 111.4 . . ?
H22A C22S H22B 109.3 . . ?
C24S C23S C22S 102.2(3) . . ?
C24S C23S H23A 111.3 . . ?
C22S C23S H23A 111.3 . . ?
C24S C23S H23B 111.3 . . ?
C22S C23S H23B 111.3 . . ?
H23A C23S H23B 109.2 . . ?
O2 C24S C23S 106.6(3) . . ?
O2 C24S H24A 110.4 . . ?
C23S C24S H24A 110.4 . . ?
O2 C24S H24B 110.4 . . ?
C23S C24S H24B 110.4 . . ?
H24A C24S H24B 108.6 . . ?
O2 C21S C22S 107.3(3) . . ?
O2 C21S H21A 110.3 . . ?
C22S C21S H21A 110.3 . . ?
O2 C21S H21B 110.3 . . ?
C22S C21S H21B 110.3 . . ?
H21A C21S H21B 108.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.087

