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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  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_1e

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
4-(Diethylphosphino)-1-(4-trifluoromethylphenyl)-1H-1,2,3-triazole
;
_chemical_name_common            ?
_chemical_melting_point          336
_chemical_formula_moiety         'C13 H15 F3 N3 P'
_chemical_formula_sum            'C13 H15 F3 N3 P'
_chemical_formula_weight         301.25

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 2(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                   5.4783(5)
_cell_length_b                   6.9229(6)
_cell_length_c                   18.7771(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.059(3)
_cell_angle_gamma                90.00
_cell_volume                     709.36(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    4682
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      30.39

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8283
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         29.56
_reflns_number_total             3679
_reflns_number_gt                3267
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0459P)²+0.1786P] 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   0.01(10)
_refine_ls_number_reflns         3679
_refine_ls_number_parameters     183
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1029
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.110
_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
P1 P 0.22817(10) 1.06842(8) 0.15158(3) 0.02140(12) Uani 1 1 d . . .
F3 F 0.0642(4) -0.0254(3) 0.50228(9) 0.0649(6) Uani 1 1 d . . .
F2 F -0.1071(4) -0.1560(3) 0.40626(11) 0.0753(8) Uani 1 1 d . . .
F1 F 0.2717(4) -0.1885(3) 0.43496(11) 0.0620(6) Uani 1 1 d . . .
C3 C 0.2414(4) 0.4497(3) 0.32067(11) 0.0205(4) Uani 1 1 d . . .
C12 C 0.5084(4) 1.2152(3) 0.16906(11) 0.0243(4) Uani 1 1 d . . .
H12A H 0.5257 1.2543 0.2200 0.029 Uiso 1 1 calc R . .
H12B H 0.6529 1.1360 0.1600 0.029 Uiso 1 1 calc R . .
C6 C 0.1404(4) 0.1168(3) 0.39327(11) 0.0236(5) Uani 1 1 d . . .
C7 C 0.3519(4) 0.2211(4) 0.41344(11) 0.0273(5) Uani 1 1 d . . .
H7 H 0.4608 0.1776 0.4523 0.033 Uiso 1 1 calc R . .
C2 C 0.1517(4) 0.7428(3) 0.24312(11) 0.0208(4) Uani 1 1 d . . .
H2 H -0.0223 0.7425 0.2379 0.025 Uiso 1 1 calc R . .
C5 C -0.0207(4) 0.1804(3) 0.33662(12) 0.0245(4) Uani 1 1 d . . .
H5 H -0.1656 0.1093 0.3230 0.029 Uiso 1 1 calc R . .
C10 C 0.2930(5) 0.9482(4) 0.06728(12) 0.0288(5) Uani 1 1 d . . .
H10A H 0.3191 1.0480 0.0310 0.035 Uiso 1 1 calc R . .
H10B H 0.4463 0.8727 0.0756 0.035 Uiso 1 1 calc R . .
C9 C 0.0860(5) -0.0608(4) 0.43376(13) 0.0323(5) Uani 1 1 d . . .
C4 C 0.0304(4) 0.3475(3) 0.30000(11) 0.0237(4) Uani 1 1 d . . .
H4 H -0.0785 0.3912 0.2612 0.028 Uiso 1 1 calc R . .
C8 C 0.4050(4) 0.3877(4) 0.37737(11) 0.0258(5) Uani 1 1 d . . .
H8 H 0.5500 0.4588 0.3909 0.031 Uiso 1 1 calc R . .
C1 C 0.3055(4) 0.8703(3) 0.21294(10) 0.0203(4) Uani 1 1 d . . .
C13 C 0.5028(5) 1.3950(4) 0.12229(13) 0.0351(6) Uani 1 1 d . . .
H13A H 0.4980 1.3567 0.0719 0.053 Uiso 1 1 calc R . .
H13B H 0.6500 1.4724 0.1349 0.053 Uiso 1 1 calc R . .
H13C H 0.3569 1.4715 0.1299 0.053 Uiso 1 1 calc R . .
C11 C 0.0876(5) 0.8146(4) 0.03834(14) 0.0398(6) Uani 1 1 d . . .
H11A H 0.0658 0.7119 0.0731 0.060 Uiso 1 1 calc R . .
H11B H 0.1293 0.7573 -0.0067 0.060 Uiso 1 1 calc R . .
H11C H -0.0649 0.8884 0.0300 0.060 Uiso 1 1 calc R . .
N1 N 0.3008(3) 0.6175(2) 0.28189(9) 0.0201(4) Uani 1 1 d . . .
N3 N 0.5423(3) 0.8159(3) 0.23521(10) 0.0266(4) Uani 1 1 d . . .
N2 N 0.5390(3) 0.6648(3) 0.27645(10) 0.0261(4) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C1 1.817(2) . ?
P1 C12 1.846(2) . ?
P1 C10 1.850(2) . ?
F3 C9 1.325(3) . ?
F2 C9 1.313(3) . ?
F1 C9 1.346(3) . ?
C3 C4 1.381(3) . ?
C3 C8 1.397(3) . ?
C3 N1 1.424(3) . ?
C12 C13 1.522(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C6 C7 1.389(3) . ?
C6 C5 1.392(3) . ?
C6 C9 1.490(3) . ?
C7 C8 1.381(3) . ?
C7 H7 0.9500 . ?
C2 N1 1.358(3) . ?
C2 C1 1.376(3) . ?
C2 H2 0.9500 . ?
C5 C4 1.387(3) . ?
C5 H5 0.9500 . ?
C10 C11 1.520(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C4 H4 0.9500 . ?
C8 H8 0.9500 . ?
C1 N3 1.380(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N1 N2 1.358(3) . ?
N3 N2 1.302(3) . ?

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 P1 C12 99.16(10) . . ?
C1 P1 C10 98.71(10) . . ?
C12 P1 C10 100.39(11) . . ?
C4 C3 C8 121.4(2) . . ?
C4 C3 N1 119.85(19) . . ?
C8 C3 N1 118.7(2) . . ?
C13 C12 P1 111.92(16) . . ?
C13 C12 H12A 109.2 . . ?
P1 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
P1 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C7 C6 C5 120.1(2) . . ?
C7 C6 C9 119.3(2) . . ?
C5 C6 C9 120.6(2) . . ?
C8 C7 C6 120.4(2) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
N1 C2 C1 105.63(18) . . ?
N1 C2 H2 127.2 . . ?
C1 C2 H2 127.2 . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C11 C10 P1 112.82(18) . . ?
C11 C10 H10A 109.0 . . ?
P1 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
P1 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
F2 C9 F3 109.6(2) . . ?
F2 C9 F1 105.0(2) . . ?
F3 C9 F1 103.8(2) . . ?
F2 C9 C6 113.8(2) . . ?
F3 C9 C6 112.5(2) . . ?
F1 C9 C6 111.5(2) . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C7 C8 C3 118.8(2) . . ?
C7 C8 H8 120.6 . . ?
C3 C8 H8 120.6 . . ?
C2 C1 N3 107.06(19) . . ?
C2 C1 P1 128.93(16) . . ?
N3 C1 P1 123.95(16) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 N1 C2 110.00(17) . . ?
N2 N1 C3 119.99(17) . . ?
C2 N1 C3 129.89(19) . . ?
N2 N3 C1 109.70(18) . . ?
N3 N2 N1 107.61(17) . . ?

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        29.56
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 986144'
#######################################################################
#
#                 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_1i

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
1-Benzyl-4-(diphenylphosphino)-1H-1,2,3-triazole 
;
_chemical_name_common            ?
_chemical_melting_point          371
_chemical_formula_moiety         'C21 H18 N3 P'
_chemical_formula_sum            'C21 H18 N3 P'
_chemical_formula_weight         343.35

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   10.0928(3)
_cell_length_b                   10.6178(3)
_cell_length_c                   17.3125(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.415(2)
_cell_angle_gamma                90.00
_cell_volume                     1835.29(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    9962
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      26.38

_exptl_crystal_description       stick
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      291(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43181
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         28.71
_reflns_number_total             4717
_reflns_number_gt                3603
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0478P)²+0.3360P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4717
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1050
_refine_ls_wR_factor_gt          0.0942
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
P1 P 0.17703(3) 0.15871(3) 0.137473(19) 0.04365(11) Uani 1 1 d . . .
C16 C 0.20369(13) 0.16398(12) 0.03513(7) 0.0432(3) Uani 1 1 d . . .
C1 C 0.34084(13) 0.20125(12) 0.18863(7) 0.0425(3) Uani 1 1 d . . .
C4 C 0.67210(12) 0.18105(12) 0.38628(8) 0.0450(3) Uani 1 1 d . . .
C10 C 0.07816(13) 0.30169(12) 0.14522(7) 0.0439(3) Uani 1 1 d . . .
C3 C 0.66641(15) 0.14943(16) 0.30131(9) 0.0538(3) Uani 1 1 d . . .
C2 C 0.43163(14) 0.11952(13) 0.22830(8) 0.0472(3) Uani 1 1 d . . .
C9 C 0.71307(15) 0.29854(15) 0.41508(10) 0.0563(4) Uani 1 1 d . . .
C11 C -0.01644(15) 0.30008(16) 0.19589(8) 0.0553(3) Uani 1 1 d . . .
C17 C 0.09362(15) 0.13935(15) -0.02059(9) 0.0546(3) Uani 1 1 d . . .
C13 C -0.08220(17) 0.51107(17) 0.16048(10) 0.0641(4) Uani 1 1 d . . .
C8 C 0.71848(18) 0.32559(18) 0.49318(11) 0.0671(4) Uani 1 1 d . . .
C5 C 0.63743(16) 0.09105(15) 0.43756(10) 0.0587(4) Uani 1 1 d . . .
C14 C 0.01060(18) 0.51401(16) 0.10970(11) 0.0661(4) Uani 1 1 d . . .
C18 C 0.10550(18) 0.12881(18) -0.09853(9) 0.0654(4) Uani 1 1 d . . .
C12 C -0.09534(18) 0.40481(18) 0.20353(10) 0.0675(4) Uani 1 1 d . . .
C19 C 0.22752(19) 0.14331(18) -0.12268(10) 0.0690(5) Uani 1 1 d . . .
C7 C 0.68381(17) 0.2356(2) 0.54366(10) 0.0695(5) Uani 1 1 d . . .
C15 C 0.09006(16) 0.41005(14) 0.10190(10) 0.0588(4) Uani 1 1 d . . .
C21 C 0.32609(17) 0.1786(2) 0.00980(10) 0.0704(5) Uani 1 1 d . . .
C6 C 0.64409(18) 0.1185(2) 0.51600(11) 0.0714(5) Uani 1 1 d . . .
C20 C 0.3372(2) 0.1687(2) -0.06866(11) 0.0832(6) Uani 1 1 d . . .
N3 N 0.53996(11) 0.18855(10) 0.25423(6) 0.0453(3) Uani 1 1 d . . .
N2 N 0.51993(13) 0.30943(10) 0.23305(7) 0.0553(3) Uani 1 1 d . . .
N1 N 0.39949(13) 0.31759(10) 0.19305(7) 0.0538(3) Uani 1 1 d . . .
H2 H 0.4276(16) 0.0342(17) 0.2376(9) 0.065(5) Uiso 1 1 d . . .
H3A H 0.7368(18) 0.1920(16) 0.2815(10) 0.065(5) Uiso 1 1 d . . .
H3B H 0.6752(16) 0.0607(18) 0.2940(9) 0.064(5) Uiso 1 1 d . . .
H5 H 0.6116(17) 0.0097(17) 0.4177(10) 0.069(5) Uiso 1 1 d . . .
H9 H 0.737(2) 0.360(2) 0.3795(11) 0.084(6) Uiso 1 1 d . . .
H8 H 0.7468(19) 0.407(2) 0.5117(11) 0.083(6) Uiso 1 1 d . . .
H6 H 0.622(2) 0.054(2) 0.5512(12) 0.091(6) Uiso 1 1 d . . .
H7 H 0.6887(19) 0.2551(19) 0.5974(12) 0.086(6) Uiso 1 1 d . . .
H15 H 0.1560(17) 0.4121(16) 0.0674(9) 0.067(5) Uiso 1 1 d . . .
H11 H -0.0234(18) 0.2229(19) 0.2263(11) 0.079(5) Uiso 1 1 d . . .
H13 H -0.1378(19) 0.5827(19) 0.1643(11) 0.080(5) Uiso 1 1 d . . .
H14 H 0.0220(19) 0.5822(19) 0.0788(11) 0.080(6) Uiso 1 1 d . . .
H12 H -0.163(2) 0.402(2) 0.2393(12) 0.092(6) Uiso 1 1 d . . .
H17 H 0.0058(19) 0.1283(17) -0.0040(10) 0.067(5) Uiso 1 1 d . . .
H19 H 0.2358(19) 0.1381(18) -0.1748(11) 0.080(5) Uiso 1 1 d . . .
H21 H 0.402(2) 0.1900(19) 0.0454(12) 0.095(7) Uiso 1 1 d . . .
H18 H 0.029(2) 0.1077(19) -0.1342(11) 0.088(6) Uiso 1 1 d . . .
H20 H 0.422(2) 0.176(2) -0.0842(13) 0.105(7) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C1 1.8147(13) . ?
P1 C16 1.8315(13) . ?
P1 C10 1.8325(14) . ?
C16 C21 1.379(2) . ?
C16 C17 1.3855(19) . ?
C1 N1 1.3670(17) . ?
C1 C2 1.3713(18) . ?
C4 C5 1.384(2) . ?
C4 C9 1.384(2) . ?
C4 C3 1.502(2) . ?
C10 C11 1.3881(19) . ?
C10 C15 1.3881(19) . ?
C3 N3 1.4701(17) . ?
C3 H3A 0.947(18) . ?
C3 H3B 0.956(19) . ?
C2 N3 1.3382(17) . ?
C2 H2 0.923(18) . ?
C9 C8 1.375(2) . ?
C9 H9 0.95(2) . ?
C11 C12 1.385(2) . ?
C11 H11 0.982(19) . ?
C17 C18 1.377(2) . ?
C17 H17 0.978(18) . ?
C13 C12 1.369(3) . ?
C13 C14 1.376(3) . ?
C13 H13 0.95(2) . ?
C8 C7 1.375(3) . ?
C8 H8 0.95(2) . ?
C5 C6 1.381(3) . ?
C5 H5 0.952(18) . ?
C14 C15 1.383(2) . ?
C14 H14 0.92(2) . ?
C18 C19 1.366(3) . ?
C18 H18 0.94(2) . ?
C12 H12 0.98(2) . ?
C19 C20 1.367(3) . ?
C19 H19 0.920(18) . ?
C7 C6 1.371(3) . ?
C7 H7 0.95(2) . ?
C15 H15 0.957(17) . ?
C21 C20 1.383(2) . ?
C21 H21 0.92(2) . ?
C6 H6 0.96(2) . ?
C20 H20 0.94(2) . ?
N3 N2 1.3420(15) . ?
N2 N1 1.3108(17) . ?

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 P1 C16 102.25(6) . . ?
C1 P1 C10 103.00(6) . . ?
C16 P1 C10 101.78(6) . . ?
C21 C16 C17 117.67(13) . . ?
C21 C16 P1 125.20(11) . . ?
C17 C16 P1 116.84(10) . . ?
N1 C1 C2 106.96(12) . . ?
N1 C1 P1 127.47(10) . . ?
C2 C1 P1 125.53(10) . . ?
C5 C4 C9 118.79(14) . . ?
C5 C4 C3 119.81(14) . . ?
C9 C4 C3 121.40(14) . . ?
C11 C10 C15 118.27(14) . . ?
C11 C10 P1 117.93(11) . . ?
C15 C10 P1 123.79(11) . . ?
N3 C3 C4 112.68(11) . . ?
N3 C3 H3A 107.5(10) . . ?
C4 C3 H3A 109.0(10) . . ?
N3 C3 H3B 107.2(10) . . ?
C4 C3 H3B 111.0(10) . . ?
H3A C3 H3B 109.5(14) . . ?
N3 C2 C1 105.94(12) . . ?
N3 C2 H2 122.3(10) . . ?
C1 C2 H2 131.8(10) . . ?
C8 C9 C4 120.61(16) . . ?
C8 C9 H9 120.9(12) . . ?
C4 C9 H9 118.5(12) . . ?
C12 C11 C10 120.58(15) . . ?
C12 C11 H11 122.1(11) . . ?
C10 C11 H11 117.3(11) . . ?
C18 C17 C16 121.46(14) . . ?
C18 C17 H17 119.4(10) . . ?
C16 C17 H17 119.1(10) . . ?
C12 C13 C14 119.72(16) . . ?
C12 C13 H13 120.9(11) . . ?
C14 C13 H13 119.3(11) . . ?
C7 C8 C9 120.17(17) . . ?
C7 C8 H8 120.6(11) . . ?
C9 C8 H8 119.3(11) . . ?
C6 C5 C4 120.31(16) . . ?
C6 C5 H5 121.2(10) . . ?
C4 C5 H5 118.4(10) . . ?
C13 C14 C15 120.22(16) . . ?
C13 C14 H14 123.0(12) . . ?
C15 C14 H14 116.7(12) . . ?
C19 C18 C17 120.18(15) . . ?
C19 C18 H18 121.1(12) . . ?
C17 C18 H18 118.7(12) . . ?
C13 C12 C11 120.44(16) . . ?
C13 C12 H12 120.1(12) . . ?
C11 C12 H12 119.5(12) . . ?
C18 C19 C20 119.25(16) . . ?
C18 C19 H19 120.6(12) . . ?
C20 C19 H19 120.1(12) . . ?
C6 C7 C8 119.81(17) . . ?
C6 C7 H7 120.8(13) . . ?
C8 C7 H7 119.4(13) . . ?
C14 C15 C10 120.77(16) . . ?
C14 C15 H15 120.6(11) . . ?
C10 C15 H15 118.6(11) . . ?
C16 C21 C20 120.58(16) . . ?
C16 C21 H21 119.9(13) . . ?
C20 C21 H21 119.4(13) . . ?
C7 C6 C5 120.30(17) . . ?
C7 C6 H6 120.4(12) . . ?
C5 C6 H6 119.3(12) . . ?
C19 C20 C21 120.87(17) . . ?
C19 C20 H20 120.2(14) . . ?
C21 C20 H20 118.9(14) . . ?
C2 N3 N2 110.44(11) . . ?
C2 N3 C3 129.17(12) . . ?
N2 N3 C3 120.37(12) . . ?
N1 N2 N3 107.37(10) . . ?
N2 N1 C1 109.29(10) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.71
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.037
_database_code_depnum_ccdc_archive 'CCDC 986145'
#######################################################################
#
#                 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_1j

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 1-(4-Bromophenyl)-4-(diphenylphosphino)-1H-1,2,3-triazole 
;
_chemical_name_common            ?
_chemical_melting_point          393
_chemical_formula_moiety         'C20 H15 Br N3 P'
_chemical_formula_sum            'C20 H15 Br N3 P'
_chemical_formula_weight         408.23

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.7216(2)
_cell_length_b                   12.5095(5)
_cell_length_c                   12.5281(5)
_cell_angle_alpha                86.643(2)
_cell_angle_beta                 79.834(2)
_cell_angle_gamma                82.749(2)
_cell_volume                     874.95(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5148
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      32.05

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_absorpt_coefficient_mu    2.448
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.3637
_exptl_absorpt_correction_T_max  0.8339
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11222
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         28.69
_reflns_number_total             4448
_reflns_number_gt                3772
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0287P)²+0.2794P] 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         4448
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0630
_refine_ls_wR_factor_gt          0.0597
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
Br1 Br 0.34315(3) 0.187970(15) -0.038353(15) 0.02828(6) Uani 1 1 d . . .
P1 P 0.61961(8) 0.77724(3) 0.39387(3) 0.01895(9) Uani 1 1 d . . .
N1 N 0.6661(2) 0.53165(11) 0.20587(11) 0.0169(3) Uani 1 1 d . . .
N2 N 0.9014(2) 0.54611(11) 0.19147(11) 0.0201(3) Uani 1 1 d . . .
N3 N 0.9194(2) 0.62503(11) 0.25252(11) 0.0203(3) Uani 1 1 d . . .
C1 C 0.4471(3) 0.29258(13) 0.03990(13) 0.0186(3) Uani 1 1 d . . .
C2 C 0.3120(3) 0.32543(13) 0.13746(14) 0.0206(3) Uani 1 1 d . . .
H2 H 0.1690 0.2949 0.1659 0.025 Uiso 1 1 calc R . .
C3 C 0.3871(3) 0.40348(13) 0.19356(13) 0.0190(3) Uani 1 1 d . . .
H3 H 0.2972 0.4259 0.2614 0.023 Uiso 1 1 calc R . .
C4 C 0.5935(3) 0.44841(12) 0.15016(13) 0.0167(3) Uani 1 1 d . . .
C5 C 0.5347(3) 0.60245(13) 0.27667(13) 0.0180(3) Uani 1 1 d . . .
H5 H 0.3666 0.6093 0.3006 0.022 Uiso 1 1 calc R . .
C6 C 0.6962(3) 0.66246(12) 0.30667(13) 0.0176(3) Uani 1 1 d . . .
C7 C 0.8527(3) 0.75754(14) 0.47909(13) 0.0204(3) Uani 1 1 d . . .
C8 C 0.8996(3) 0.84782(15) 0.52855(15) 0.0271(4) Uani 1 1 d . . .
H8 H 0.8249 0.9172 0.5107 0.032 Uiso 1 1 calc R . .
C9 C 1.0533(4) 0.83767(16) 0.60313(15) 0.0310(4) Uani 1 1 d . . .
H9 H 1.0830 0.9000 0.6361 0.037 Uiso 1 1 calc R . .
C10 C 1.1640(3) 0.73753(16) 0.63016(14) 0.0297(4) Uani 1 1 d . . .
H10 H 1.2688 0.7307 0.6818 0.036 Uiso 1 1 calc R . .
C11 C 0.9658(3) 0.65701(14) 0.50620(14) 0.0261(4) Uani 1 1 d . . .
H11 H 0.9370 0.5945 0.4733 0.031 Uiso 1 1 calc R . .
C12 C 1.1207(4) 0.64748(16) 0.58124(15) 0.0302(4) Uani 1 1 d . . .
H12 H 1.1973 0.5785 0.5990 0.036 Uiso 1 1 calc R . .
C13 C 0.7196(3) 0.88660(13) 0.29945(13) 0.0186(3) Uani 1 1 d . . .
C14 C 0.5450(3) 0.97144(14) 0.28374(14) 0.0240(4) Uani 1 1 d . . .
H14 H 0.3878 0.9718 0.3241 0.029 Uiso 1 1 calc R . .
C15 C 0.5985(4) 1.05557(15) 0.20962(16) 0.0299(4) Uani 1 1 d . . .
H15 H 0.4788 1.1135 0.1999 0.036 Uiso 1 1 calc R . .
C16 C 0.8258(4) 1.05490(15) 0.15018(15) 0.0292(4) Uani 1 1 d . . .
H16 H 0.8616 1.1117 0.0984 0.035 Uiso 1 1 calc R . .
C17 C 1.0025(3) 0.97147(14) 0.16572(14) 0.0259(4) Uani 1 1 d . . .
H17 H 1.1592 0.9716 0.1250 0.031 Uiso 1 1 calc R . .
C18 C 0.9504(3) 0.88801(13) 0.24060(14) 0.0215(3) Uani 1 1 d . . .
H18 H 1.0722 0.8316 0.2519 0.026 Uiso 1 1 calc R . .
C19 C 0.7294(3) 0.41390(14) 0.05278(14) 0.0230(4) Uani 1 1 d . . .
H19 H 0.8722 0.4445 0.0241 0.028 Uiso 1 1 calc R . .
C20 C 0.6572(3) 0.33506(14) -0.00251(14) 0.0229(4) Uani 1 1 d . . .
H20 H 0.7507 0.3103 -0.0688 0.027 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
Br1 C1 1.8919(16) . ?
P1 C6 1.8174(16) . ?
P1 C13 1.8350(17) . ?
P1 C7 1.8352(17) . ?
N1 C5 1.351(2) . ?
N1 N2 1.3596(18) . ?
N1 C4 1.428(2) . ?
N2 N3 1.3086(19) . ?
N3 C6 1.375(2) . ?
C1 C2 1.380(2) . ?
C1 C20 1.383(2) . ?
C2 C3 1.387(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(2) . ?
C3 H3 0.9500 . ?
C4 C19 1.386(2) . ?
C5 C6 1.375(2) . ?
C5 H5 0.9500 . ?
C7 C11 1.392(2) . ?
C7 C8 1.396(2) . ?
C8 C9 1.382(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(3) . ?
C9 H9 0.9500 . ?
C10 C12 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.393(2) . ?
C13 C18 1.396(2) . ?
C14 C15 1.389(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.381(2) . ?
C19 H19 0.9500 . ?
C20 H20 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
C6 P1 C13 101.05(7) . . ?
C6 P1 C7 102.68(7) . . ?
C13 P1 C7 101.87(7) . . ?
C5 N1 N2 110.53(13) . . ?
C5 N1 C4 129.94(13) . . ?
N2 N1 C4 119.52(13) . . ?
N3 N2 N1 107.19(13) . . ?
N2 N3 C6 109.35(13) . . ?
C2 C1 C20 121.33(15) . . ?
C2 C1 Br1 119.64(12) . . ?
C20 C1 Br1 119.03(13) . . ?
C1 C2 C3 119.36(15) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 119.60(15) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C19 120.56(15) . . ?
C3 C4 N1 119.63(14) . . ?
C19 C4 N1 119.80(14) . . ?
N1 C5 C6 105.24(14) . . ?
N1 C5 H5 127.4 . . ?
C6 C5 H5 127.4 . . ?
C5 C6 N3 107.69(14) . . ?
C5 C6 P1 125.14(13) . . ?
N3 C6 P1 127.00(12) . . ?
C11 C7 C8 118.36(16) . . ?
C11 C7 P1 123.81(13) . . ?
C8 C7 P1 117.45(13) . . ?
C9 C8 C7 120.88(17) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.49(18) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C12 C10 C9 119.27(17) . . ?
C12 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C7 C11 C12 120.42(17) . . ?
C7 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C10 C12 C11 120.57(18) . . ?
C10 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C18 119.00(16) . . ?
C14 C13 P1 115.91(13) . . ?
C18 C13 P1 125.04(13) . . ?
C15 C14 C13 120.60(17) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 119.89(17) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.19(17) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 120.06(17) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C13 120.23(16) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
C20 C19 C4 120.00(16) . . ?
C20 C19 H19 120.0 . . ?
C4 C19 H19 120.0 . . ?
C19 C20 C1 119.11(16) . . ?
C19 C20 H20 120.4 . . ?
C1 C20 H20 120.4 . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        28.69
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 986146'
#######################################################################
#
#                 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_2c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 1-(4-Anisyl)-4-(diethylphosphino-borane)-1H-1,2,3-triazole 
;
_chemical_name_common            ?
_chemical_melting_point          338
_chemical_formula_moiety         'C13 H21 B N3 O P'
_chemical_formula_sum            'C13 H21 B N3 O P'
_chemical_formula_weight         277.11

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   15.8190(3)
_cell_length_b                   7.26290(10)
_cell_length_c                   13.1199(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.5540(10)
_cell_angle_gamma                90.00
_cell_volume                     1502.61(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    9651
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      30.33

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      291(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28283
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         30.03
_reflns_number_total             4391
_reflns_number_gt                3248
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0870P)²+0.1686P] 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_number_reflns         4391
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1454
_refine_ls_wR_factor_gt          0.1236
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
P1 P 0.32746(2) 0.36897(5) 0.44919(2) 0.04151(13) Uani 1 1 d . . .
N1 N 0.08896(7) 0.36753(14) 0.33670(8) 0.0369(2) Uani 1 1 d . . .
N2 N 0.08151(8) 0.3616(2) 0.43831(10) 0.0523(3) Uani 1 1 d . . .
N3 N 0.15783(8) 0.3635(2) 0.48405(9) 0.0522(3) Uani 1 1 d . . .
C3 C 0.01483(8) 0.37064(16) 0.26703(10) 0.0356(3) Uani 1 1 d . . .
C1 C 0.21560(9) 0.36944(19) 0.41261(10) 0.0394(3) Uani 1 1 d . . .
C6 C -0.12961(9) 0.38049(18) 0.13328(11) 0.0401(3) Uani 1 1 d . . .
C5 C -0.05140(9) 0.3440(2) 0.09685(11) 0.0421(3) Uani 1 1 d . . .
C4 C 0.02067(9) 0.33873(19) 0.16431(11) 0.0399(3) Uani 1 1 d . . .
C2 C 0.17152(9) 0.3712(2) 0.31834(10) 0.0411(3) Uani 1 1 d . . .
C8 C -0.06324(9) 0.4076(2) 0.30416(11) 0.0416(3) Uani 1 1 d . . .
C7 C -0.13487(9) 0.4118(2) 0.23764(11) 0.0445(3) Uani 1 1 d . . .
C12 C 0.36785(10) 0.1849(3) 0.37355(13) 0.0509(4) Uani 1 1 d . . .
C10 C 0.37009(11) 0.5836(3) 0.40351(13) 0.0537(4) Uani 1 1 d . . .
C9 C -0.20201(13) 0.3636(3) -0.03274(14) 0.0593(4) Uani 1 1 d . . .
C11 C 0.35196(14) 0.6299(3) 0.29160(16) 0.0672(5) Uani 1 1 d . . .
H11A H 0.3722 0.5322 0.2507 0.101 Uiso 1 1 calc R . .
H11B H 0.3802 0.7425 0.2766 0.101 Uiso 1 1 calc R . .
H11C H 0.2920 0.6443 0.2765 0.101 Uiso 1 1 calc R . .
C13 C 0.46348(13) 0.1711(3) 0.3815(2) 0.0824(6) Uani 1 1 d . . .
H13A H 0.4869 0.2807 0.3542 0.124 Uiso 1 1 calc R . .
H13B H 0.4803 0.0661 0.3434 0.124 Uiso 1 1 calc R . .
H13C H 0.4840 0.1576 0.4519 0.124 Uiso 1 1 calc R . .
B1 B 0.35140(15) 0.3438(4) 0.59397(14) 0.0626(5) Uani 1 1 d . . .
O1 O -0.20432(7) 0.38906(16) 0.07450(9) 0.0535(3) Uani 1 1 d . . .
H14 H 0.4325(13) 0.577(3) 0.4206(14) 0.063(5) Uiso 1 1 d . . .
H10 H 0.3522(13) 0.202(3) 0.3062(18) 0.078(6) Uiso 1 1 d . . .
H2 H 0.0725(12) 0.306(3) 0.1416(14) 0.059(5) Uiso 1 1 d . . .
H4 H -0.1881(10) 0.447(3) 0.2613(12) 0.052(4) Uiso 1 1 d . . .
H8 H -0.2575(17) 0.381(3) -0.0572(19) 0.084(7) Uiso 1 1 d . . .
H9 H 0.3482(12) 0.070(3) 0.3948(15) 0.062(5) Uiso 1 1 d . . .
H6 H -0.1815(13) 0.249(4) -0.0450(15) 0.074(6) Uiso 1 1 d . . .
H5 H -0.0626(11) 0.435(3) 0.3739(14) 0.057(5) Uiso 1 1 d . . .
H3 H -0.0457(11) 0.318(3) 0.0261(14) 0.059(5) Uiso 1 1 d . . .
H15 H 0.3567(13) 0.675(3) 0.4423(16) 0.074(6) Uiso 1 1 d . . .
H7 H -0.1626(13) 0.458(3) -0.0589(15) 0.083(7) Uiso 1 1 d . . .
H1 H 0.1879(13) 0.372(2) 0.2530(16) 0.063(6) Uiso 1 1 d . . .
H16 H 0.4275(16) 0.342(3) 0.6060(18) 0.089(7) Uiso 1 1 d . . .
H17 H 0.3219(15) 0.223(4) 0.6164(19) 0.098(7) Uiso 1 1 d . . .
H18 H 0.3303(15) 0.463(4) 0.6271(19) 0.101(8) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C1 1.7963(14) . ?
P1 C12 1.8116(17) . ?
P1 C10 1.8191(18) . ?
P1 B1 1.9159(19) . ?
N1 C2 1.3470(17) . ?
N1 N2 1.3483(16) . ?
N1 C3 1.4287(18) . ?
N2 N3 1.3049(19) . ?
N3 C1 1.3607(17) . ?
C3 C4 1.3778(19) . ?
C3 C8 1.3893(18) . ?
C1 C2 1.3708(19) . ?
C6 O1 1.3604(17) . ?
C6 C5 1.3868(19) . ?
C6 C7 1.397(2) . ?
C5 C4 1.387(2) . ?
C5 H3 0.959(19) . ?
C4 H2 0.924(19) . ?
C2 H1 0.92(2) . ?
C8 C7 1.374(2) . ?
C8 H5 0.935(18) . ?
C7 H4 0.956(16) . ?
C12 C13 1.511(3) . ?
C12 H10 0.91(2) . ?
C12 H9 0.94(2) . ?
C10 C11 1.511(3) . ?
C10 H14 1.00(2) . ?
C10 H15 0.88(2) . ?
C9 O1 1.423(2) . ?
C9 H8 0.92(3) . ?
C9 H6 0.91(2) . ?
C9 H7 1.01(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
B1 H16 1.20(2) . ?
B1 H17 1.05(3) . ?
B1 H18 1.03(3) . ?

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 P1 C12 103.76(7) . . ?
C1 P1 C10 107.07(7) . . ?
C12 P1 C10 107.22(9) . . ?
C1 P1 B1 112.21(8) . . ?
C12 P1 B1 114.98(10) . . ?
C10 P1 B1 111.04(10) . . ?
C2 N1 N2 109.85(12) . . ?
C2 N1 C3 130.06(11) . . ?
N2 N1 C3 120.09(11) . . ?
N3 N2 N1 107.70(11) . . ?
N2 N3 C1 109.33(11) . . ?
C4 C3 C8 120.40(14) . . ?
C4 C3 N1 120.51(12) . . ?
C8 C3 N1 119.09(12) . . ?
N3 C1 C2 107.49(12) . . ?
N3 C1 P1 121.14(10) . . ?
C2 C1 P1 131.36(10) . . ?
O1 C6 C5 124.90(13) . . ?
O1 C6 C7 115.56(12) . . ?
C5 C6 C7 119.54(14) . . ?
C6 C5 C4 119.73(13) . . ?
C6 C5 H3 121.8(11) . . ?
C4 C5 H3 118.5(11) . . ?
C3 C4 C5 120.26(13) . . ?
C3 C4 H2 119.2(11) . . ?
C5 C4 H2 120.4(11) . . ?
N1 C2 C1 105.63(12) . . ?
N1 C2 H1 121.3(13) . . ?
C1 C2 H1 133.1(13) . . ?
C7 C8 C3 119.51(13) . . ?
C7 C8 H5 124.1(11) . . ?
C3 C8 H5 116.3(11) . . ?
C8 C7 C6 120.56(13) . . ?
C8 C7 H4 120.2(10) . . ?
C6 C7 H4 119.0(10) . . ?
C13 C12 P1 113.94(14) . . ?
C13 C12 H10 105.7(13) . . ?
P1 C12 H10 110.7(14) . . ?
C13 C12 H9 105.9(11) . . ?
P1 C12 H9 110.6(12) . . ?
H10 C12 H9 109.8(18) . . ?
C11 C10 P1 117.63(12) . . ?
C11 C10 H14 109.7(11) . . ?
P1 C10 H14 105.9(11) . . ?
C11 C10 H15 111.1(14) . . ?
P1 C10 H15 110.4(15) . . ?
H14 C10 H15 100.7(17) . . ?
O1 C9 H8 103.2(16) . . ?
O1 C9 H6 109.3(13) . . ?
H8 C9 H6 114.1(18) . . ?
O1 C9 H7 108.3(12) . . ?
H8 C9 H7 112.7(18) . . ?
H6 C9 H7 108.9(19) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
P1 B1 H16 104.4(11) . . ?
P1 B1 H17 107.5(14) . . ?
H16 B1 H17 114.6(17) . . ?
P1 B1 H18 107.0(14) . . ?
H16 B1 H18 108.0(17) . . ?
H17 B1 H18 115(2) . . ?
C6 O1 C9 117.73(13) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.03
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.062
_database_code_depnum_ccdc_archive 'CCDC 986147'
#######################################################################
#
#                 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_2d

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 1-(4-Bromophenyl)-4-(diethylphosphino-borane)-1H-1,2,3-triazole 
;
_chemical_name_common            ?
_chemical_melting_point          321
_chemical_formula_moiety         'C12 H18 B Br N3 P'
_chemical_formula_sum            'C12 H18 B Br N3 P'
_chemical_formula_weight         325.98

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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   '
_symmetry_space_group_name_Hall  '-P 1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6993(2)
_cell_length_b                   10.2355(3)
_cell_length_c                   11.5727(5)
_cell_angle_alpha                105.331(2)
_cell_angle_beta                 104.973(2)
_cell_angle_gamma                107.292(2)
_cell_volume                     781.55(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    3525
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      25.76

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    2.719
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      291(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9184
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         26.73
_reflns_number_total             3307
_reflns_number_gt                2422
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0574P)²+0.4072P] 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         3307
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1234
_refine_ls_wR_factor_gt          0.1126
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
Br1 Br 1.58582(6) 0.86761(4) 1.14738(5) 0.1038(2) Uani 1 1 d . . .
P1 P 0.67447(12) -0.16345(8) 0.65449(8) 0.0611(2) Uani 1 1 d . . .
N3 N 0.7253(4) 0.1073(3) 0.6315(3) 0.0720(7) Uani 1 1 d . . .
C6 C 1.3826(5) 0.6812(3) 1.0435(3) 0.0668(8) Uani 1 1 d . . .
C7 C 1.2581(6) 0.6624(4) 0.9260(4) 0.0797(10) Uani 1 1 d . . .
H7 H 1.2700 0.7417 0.8994 0.096 Uiso 1 1 calc R . .
C8 C 1.1156(5) 0.5254(4) 0.8481(3) 0.0739(9) Uani 1 1 d . . .
H8 H 1.0301 0.5117 0.7685 0.089 Uiso 1 1 calc R . .
C3 C 1.0998(4) 0.4085(3) 0.8881(3) 0.0518(6) Uani 1 1 d . . .
N1 N 0.9569(3) 0.2659(2) 0.8051(2) 0.0511(5) Uani 1 1 d . . .
C1 C 0.9287(4) 0.1339(3) 0.8159(3) 0.0559(6) Uani 1 1 d . . .
H1 H 0.9962 0.1157 0.8850 0.067 Uiso 1 1 calc R . .
C2 C 0.7826(4) 0.0334(3) 0.7061(3) 0.0557(6) Uani 1 1 d . . .
C9 C 0.4221(5) -0.2060(4) 0.6408(4) 0.0732(9) Uani 1 1 d . . .
H9A H 0.4195 -0.1623 0.7254 0.088 Uiso 1 1 calc R . .
H9B H 0.3652 -0.1611 0.5857 0.088 Uiso 1 1 calc R . .
C10 C 0.2970(7) -0.3696(4) 0.5871(5) 0.1003(13) Uani 1 1 d . . .
H10A H 0.2852 -0.4118 0.4994 0.150 Uiso 1 1 calc R . .
H10B H 0.1696 -0.3843 0.5905 0.150 Uiso 1 1 calc R . .
H10C H 0.3571 -0.4164 0.6374 0.150 Uiso 1 1 calc R . .
N2 N 0.8296(4) 0.2470(3) 0.6906(3) 0.0687(7) Uani 1 1 d . . .
C4 C 1.2212(5) 0.4297(4) 1.0071(3) 0.0669(8) Uani 1 1 d . . .
H4 H 1.2071 0.3513 1.0351 0.080 Uiso 1 1 calc R . .
C5 C 1.3636(5) 0.5664(4) 1.0851(3) 0.0747(9) Uani 1 1 d . . .
H5 H 1.4467 0.5808 1.1658 0.090 Uiso 1 1 calc R . .
C11 C 0.6609(6) -0.2309(4) 0.4898(3) 0.0782(9) Uani 1 1 d . . .
H11A H 0.5762 -0.3348 0.4500 0.094 Uiso 1 1 calc R . .
H11B H 0.6010 -0.1799 0.4432 0.094 Uiso 1 1 calc R . .
C12 C 0.8542(7) -0.2121(6) 0.4760(6) 0.1173(16) Uani 1 1 d . . .
H12A H 0.9383 -0.1094 0.5132 0.176 Uiso 1 1 calc R . .
H12B H 0.8349 -0.2500 0.3864 0.176 Uiso 1 1 calc R . .
H12C H 0.9131 -0.2648 0.5195 0.176 Uiso 1 1 calc R . .
B1 B 0.8183(10) -0.2300(6) 0.7694(6) 0.123(2) Uani 1 1 d . . .
H1A H 0.9539 -0.1899 0.7806 0.184 Uiso 1 1 calc R . .
H1B H 0.7691 -0.3356 0.7343 0.184 Uiso 1 1 calc R . .
H1C H 0.8046 -0.1980 0.8511 0.184 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
Br1 C6 1.891(3) . ?
P1 C2 1.794(3) . ?
P1 C9 1.815(4) . ?
P1 C11 1.810(4) . ?
P1 B1 1.904(4) . ?
N3 N2 1.293(4) . ?
N3 C2 1.363(4) . ?
C6 C5 1.366(5) . ?
C6 C7 1.372(5) . ?
C7 C8 1.374(5) . ?
C7 H7 0.9300 . ?
C8 C3 1.377(4) . ?
C8 H8 0.9300 . ?
C3 C4 1.368(4) . ?
C3 N1 1.422(4) . ?
N1 N2 1.354(3) . ?
N1 C1 1.349(3) . ?
C1 C2 1.349(4) . ?
C1 H1 0.9300 . ?
C9 C10 1.516(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C4 C5 1.373(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C11 C12 1.499(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
B1 H1A 0.9600 . ?
B1 H1B 0.9600 . ?
B1 H1C 0.9600 . ?

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
C2 P1 C9 104.82(14) . . ?
C2 P1 C11 104.84(16) . . ?
C9 P1 C11 104.40(17) . . ?
C2 P1 B1 110.7(2) . . ?
C9 P1 B1 115.3(3) . . ?
C11 P1 B1 115.7(3) . . ?
N2 N3 C2 109.5(2) . . ?
C5 C6 C7 120.9(3) . . ?
C5 C6 Br1 119.7(3) . . ?
C7 C6 Br1 119.4(3) . . ?
C6 C7 C8 119.4(3) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C7 C8 C3 119.9(3) . . ?
C7 C8 H8 120.1 . . ?
C3 C8 H8 120.1 . . ?
C4 C3 C8 120.1(3) . . ?
C4 C3 N1 120.3(2) . . ?
C8 C3 N1 119.6(3) . . ?
N2 N1 C1 109.4(2) . . ?
N2 N1 C3 120.1(2) . . ?
C1 N1 C3 130.3(2) . . ?
N1 C1 C2 106.0(2) . . ?
N1 C1 H1 127.0 . . ?
C2 C1 H1 127.0 . . ?
C1 C2 N3 107.6(2) . . ?
C1 C2 P1 129.9(2) . . ?
N3 C2 P1 122.5(2) . . ?
C10 C9 P1 113.9(3) . . ?
C10 C9 H9A 108.8 . . ?
P1 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
P1 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 N2 N1 107.4(2) . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.6(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C12 C11 P1 114.5(3) . . ?
C12 C11 H11A 108.6 . . ?
P1 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
P1 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
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 . . ?
P1 B1 H1A 109.5 . . ?
P1 B1 H1B 109.5 . . ?
H1A B1 H1B 109.5 . . ?
P1 B1 H1C 109.5 . . ?
H1A B1 H1C 109.5 . . ?
H1B B1 H1C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.73
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.688
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 986148'
#######################################################################
#
#                 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_2j

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 B Br N3 P'
_chemical_formula_sum            'C20 H18 B Br N3 P'
_chemical_formula_weight         422.06

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   11.4175(3)
_cell_length_b                   15.1163(4)
_cell_length_c                   23.4211(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.935(2)
_cell_angle_gamma                90.00
_cell_volume                     3993.20(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    4905
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      28.34

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1712
_exptl_absorpt_coefficient_mu    2.147
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      291(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13208
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         28.70
_reflns_number_total             5129
_reflns_number_gt                3828
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0431P)²+3.8641P] 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         5129
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1037
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
Br1 Br -0.57237(3) 0.14738(2) 0.471096(13) 0.07235(12) Uani 1 1 d . . .
P1 P 0.24370(5) 0.15522(3) 0.68342(2) 0.03891(12) Uani 1 1 d . . .
N1 N -0.05378(16) 0.12918(11) 0.57583(7) 0.0421(4) Uani 1 1 d . . .
N2 N 0.13082(18) 0.10584(13) 0.57414(8) 0.0528(5) Uani 1 1 d . . .
N3 N 0.02650(18) 0.10188(13) 0.54260(8) 0.0520(4) Uani 1 1 d . . .
C1 C -0.4107(2) 0.13973(15) 0.50472(10) 0.0516(5) Uani 1 1 d . . .
C2 C -0.3378(2) 0.07856(15) 0.48405(10) 0.0569(6) Uani 1 1 d . . .
H2 H -0.3681 0.0404 0.4543 0.068 Uiso 1 1 calc R . .
C3 C -0.2200(2) 0.07466(15) 0.50793(10) 0.0538(5) Uani 1 1 d . . .
H3 H -0.1700 0.0337 0.4945 0.065 Uiso 1 1 calc R . .
C4 C -0.1762(2) 0.13222(13) 0.55219(9) 0.0425(4) Uani 1 1 d . . .
C5 C 0.0016(2) 0.15059(13) 0.62922(8) 0.0423(4) Uani 1 1 d . . .
H5 H -0.0330 0.1709 0.6602 0.051 Uiso 1 1 calc R . .
C6 C 0.11892(19) 0.13609(13) 0.62801(8) 0.0415(4) Uani 1 1 d . . .
C7 C 0.31222(19) 0.25438(13) 0.66075(9) 0.0427(4) Uani 1 1 d . . .
C8 C 0.3406(3) 0.32261(18) 0.69938(13) 0.0758(8) Uani 1 1 d . . .
H8 H 0.3264 0.3172 0.7373 0.091 Uiso 1 1 calc R . .
C9 C 0.3902(4) 0.3992(2) 0.68149(19) 0.1070(13) Uani 1 1 d . . .
H9 H 0.4086 0.4457 0.7073 0.128 Uiso 1 1 calc R . .
C10 C 0.4122(3) 0.4069(2) 0.62607(19) 0.0928(11) Uani 1 1 d . . .
H10 H 0.4475 0.4581 0.6147 0.111 Uiso 1 1 calc R . .
C11 C 0.3425(2) 0.06395(13) 0.67606(8) 0.0449(5) Uani 1 1 d . . .
C12 C 0.4596(2) 0.07605(17) 0.67049(11) 0.0597(6) Uani 1 1 d . . .
H12 H 0.4894 0.1329 0.6680 0.072 Uiso 1 1 calc R . .
C13 C 0.5333(3) 0.0034(2) 0.66861(13) 0.0794(9) Uani 1 1 d . . .
H13 H 0.6124 0.0116 0.6647 0.095 Uiso 1 1 calc R . .
C14 C 0.4895(4) -0.0804(2) 0.67246(12) 0.0840(10) Uani 1 1 d . . .
H14 H 0.5390 -0.1290 0.6711 0.101 Uiso 1 1 calc R . .
C15 C 0.3733(4) -0.09306(17) 0.67824(12) 0.0777(9) Uani 1 1 d . . .
H15 H 0.3444 -0.1501 0.6812 0.093 Uiso 1 1 calc R . .
C16 C 0.2989(3) -0.02167(15) 0.67967(10) 0.0621(6) Uani 1 1 d . . .
H16 H 0.2197 -0.0306 0.6830 0.075 Uiso 1 1 calc R . .
C17 C 0.3830(3) 0.34066(19) 0.58740(14) 0.0729(8) Uani 1 1 d . . .
H17 H 0.3968 0.3470 0.5495 0.088 Uiso 1 1 calc R . .
C18 C 0.3328(2) 0.26378(16) 0.60438(10) 0.0547(6) Uani 1 1 d . . .
H18 H 0.3128 0.2183 0.5779 0.066 Uiso 1 1 calc R . .
C19 C -0.2494(2) 0.19278(17) 0.57294(10) 0.0558(6) Uani 1 1 d . . .
H19 H -0.2193 0.2309 0.6028 0.067 Uiso 1 1 calc R . .
C20 C -0.3676(2) 0.19646(18) 0.54921(11) 0.0610(6) Uani 1 1 d . . .
H20 H -0.4178 0.2369 0.5631 0.073 Uiso 1 1 calc R . .
B1 B 0.1946(3) 0.1637(2) 0.75759(11) 0.0569(7) Uani 1 1 d . . .
H1A H 0.1372 0.2103 0.7570 0.085 Uiso 1 1 calc R . .
H1B H 0.2621 0.1765 0.7863 0.085 Uiso 1 1 calc R . .
H1C H 0.1599 0.1087 0.7667 0.085 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
Br1 C1 1.895(2) . ?
P1 C6 1.795(2) . ?
P1 C11 1.807(2) . ?
P1 C7 1.808(2) . ?
P1 B1 1.911(2) . ?
N1 C5 1.350(3) . ?
N1 N3 1.356(2) . ?
N1 C4 1.422(3) . ?
N2 N3 1.302(3) . ?
N2 C6 1.368(3) . ?
C1 C20 1.380(3) . ?
C1 C2 1.381(3) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(3) . ?
C3 H3 0.9300 . ?
C4 C19 1.378(3) . ?
C5 C6 1.362(3) . ?
C5 H5 0.9300 . ?
C7 C8 1.377(3) . ?
C7 C18 1.384(3) . ?
C8 C9 1.383(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.365(5) . ?
C9 H9 0.9300 . ?
C10 C17 1.357(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(3) . ?
C11 C16 1.394(3) . ?
C12 C13 1.389(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.367(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.381(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.378(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
B1 H1A 0.9600 . ?
B1 H1B 0.9600 . ?
B1 H1C 0.9600 . ?

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 P1 C11 104.19(9) . . ?
C6 P1 C7 104.61(10) . . ?
C11 P1 C7 107.45(10) . . ?
C6 P1 B1 110.86(12) . . ?
C11 P1 B1 114.43(11) . . ?
C7 P1 B1 114.36(11) . . ?
C5 N1 N3 110.10(18) . . ?
C5 N1 C4 130.05(17) . . ?
N3 N1 C4 119.85(17) . . ?
N3 N2 C6 109.00(18) . . ?
N2 N3 N1 107.51(16) . . ?
C20 C1 C2 121.1(2) . . ?
C20 C1 Br1 119.11(19) . . ?
C2 C1 Br1 119.77(18) . . ?
C3 C2 C1 119.4(2) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C19 C4 C3 120.9(2) . . ?
C19 C4 N1 119.84(19) . . ?
C3 C4 N1 119.30(19) . . ?
N1 C5 C6 105.23(17) . . ?
N1 C5 H5 127.4 . . ?
C6 C5 H5 127.4 . . ?
C5 C6 N2 108.16(19) . . ?
C5 C6 P1 129.17(15) . . ?
N2 C6 P1 122.62(16) . . ?
C8 C7 C18 119.5(2) . . ?
C8 C7 P1 119.74(18) . . ?
C18 C7 P1 120.70(17) . . ?
C7 C8 C9 119.6(3) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C17 C10 C9 120.7(3) . . ?
C17 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C16 119.4(2) . . ?
C12 C11 P1 122.54(17) . . ?
C16 C11 P1 117.98(19) . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 119.9(3) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C10 C17 C18 119.9(3) . . ?
C10 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C7 120.0(2) . . ?
C17 C18 H18 120.0 . . ?
C7 C18 H18 120.0 . . ?
C20 C19 C4 119.6(2) . . ?
C20 C19 H19 120.2 . . ?
C4 C19 H19 120.2 . . ?
C19 C20 C1 119.5(2) . . ?
C19 C20 H20 120.3 . . ?
C1 C20 H20 120.3 . . ?
P1 B1 H1A 109.5 . . ?
P1 B1 H1B 109.5 . . ?
H1A B1 H1B 109.5 . . ?
P1 B1 H1C 109.5 . . ?
H1A B1 H1C 109.5 . . ?
H1B B1 H1C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.70
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 986149'
#######################################################################
#
#                 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_2n

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 4-(Diethylphosphino-borane)-1-([2.2]-paracyclophan-4-yl)-1H-1,2,3-triazole 
;
_chemical_name_common            ?
_chemical_melting_point          413
_chemical_formula_moiety         'C22 H29 B N3 P'
_chemical_formula_sum            'C22 H29 B N3 P'
_chemical_formula_weight         377.26

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Pca2(1) '
_symmetry_space_group_name_Hall  'P 2c -2ac'

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

_cell_length_a                   11.0128(2)
_cell_length_b                   7.8943(2)
_cell_length_c                   24.9976(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2173.25(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      28.60

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      291(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34410
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         30.03
_reflns_number_total             6342
_reflns_number_gt                5510
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0729P)²+0.1252P] 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   -0.01(7)
_refine_ls_number_reflns         6342
_refine_ls_number_parameters     247
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
P1 P 0.94255(4) 1.19160(5) 0.183810(18) 0.04949(11) Uani 1 1 d . . .
C4 C 0.94087(11) 0.94740(16) -0.01268(6) 0.0383(3) Uani 1 1 d . . .
C3 C 1.01983(13) 0.80883(17) -0.01526(8) 0.0461(3) Uani 1 1 d . . .
C17 C 0.98237(12) 1.06029(18) 0.07883(7) 0.0431(3) Uani 1 1 d . . .
H17 H 1.0665 1.0513 0.0802 0.052 Uiso 1 1 calc R . .
C5 C 0.88054(14) 1.00869(17) -0.05742(6) 0.0439(3) Uani 1 1 d . . .
H5 H 0.8269 1.0990 -0.0540 0.053 Uiso 1 1 calc R . .
C8 C 1.05658(15) 0.7637(2) -0.06673(9) 0.0585(5) Uani 1 1 d . . .
H8 H 1.1218 0.6900 -0.0709 0.070 Uiso 1 1 calc R . .
C2 C 1.04095(18) 0.6881(2) 0.03005(10) 0.0615(5) Uani 1 1 d . . .
H2A H 1.0497 0.7521 0.0629 0.074 Uiso 1 1 calc R . .
H2B H 1.1164 0.6278 0.0239 0.074 Uiso 1 1 calc R . .
C11 C 0.73066(18) 0.6815(2) -0.10072(10) 0.0647(5) Uani 1 1 d . . .
C7 C 0.99850(19) 0.8257(2) -0.11159(9) 0.0625(5) Uani 1 1 d . . .
H7 H 1.0255 0.7936 -0.1454 0.075 Uiso 1 1 calc R . .
C15 C 0.74494(17) 0.6695(2) -0.00454(10) 0.0626(5) Uani 1 1 d . . .
H15 H 0.7159 0.7031 0.0287 0.075 Uiso 1 1 calc R . .
C18 C 0.90660(13) 1.12072(19) 0.11776(6) 0.0419(3) Uani 1 1 d . . .
C6 C 0.89991(18) 0.9359(2) -0.10707(7) 0.0546(4) Uani 1 1 d . . .
C16 C 0.69000(15) 0.7285(2) -0.05042(10) 0.0604(5) Uani 1 1 d . . .
H16 H 0.6241 0.8015 -0.0476 0.072 Uiso 1 1 calc R . .
C13 C 0.86635(19) 0.4850(2) -0.05720(13) 0.0755(7) Uani 1 1 d . . .
H13 H 0.9197 0.3940 -0.0597 0.091 Uiso 1 1 calc R . .
C19 C 0.8253(2) 1.3466(3) 0.19837(9) 0.0749(6) Uani 1 1 d . . .
H19A H 0.8396 1.4469 0.1769 0.090 Uiso 1 1 calc R . .
H19B H 0.7472 1.3002 0.1880 0.090 Uiso 1 1 calc R . .
C14 C 0.84499(17) 0.5586(2) -0.00775(11) 0.0687(6) Uani 1 1 d . . .
C1 C 0.9359(3) 0.5565(4) 0.03702(14) 0.0993(10) Uani 1 1 d . . .
H1A H 0.9708 0.4439 0.0395 0.119 Uiso 1 1 calc R . .
H1B H 0.8941 0.5795 0.0704 0.119 Uiso 1 1 calc R . .
C12 C 0.81009(19) 0.5441(3) -0.10263(12) 0.0716(6) Uani 1 1 d . . .
H12 H 0.8253 0.4915 -0.1352 0.086 Uiso 1 1 calc R . .
C9 C 0.8041(2) 0.9459(3) -0.15005(8) 0.0732(6) Uani 1 1 d . . .
H9A H 0.8434 0.9459 -0.1848 0.088 Uiso 1 1 calc R . .
H9B H 0.7604 1.0519 -0.1464 0.088 Uiso 1 1 calc R . .
C21 C 0.9107(2) 1.0107(3) 0.22587(8) 0.0695(6) Uani 1 1 d . . .
H21A H 0.9243 1.0419 0.2629 0.083 Uiso 1 1 calc R . .
H21B H 0.8257 0.9805 0.2221 0.083 Uiso 1 1 calc R . .
C10 C 0.7126(3) 0.7978(3) -0.14769(12) 0.0859(7) Uani 1 1 d . . .
H10A H 0.6310 0.8439 -0.1462 0.103 Uiso 1 1 calc R . .
H10B H 0.7193 0.7322 -0.1804 0.103 Uiso 1 1 calc R . .
C20 C 0.8201(4) 1.3974(4) 0.25664(11) 0.1122(12) Uani 1 1 d . . .
H20A H 0.8170 1.2977 0.2786 0.168 Uiso 1 1 calc R . .
H20B H 0.7490 1.4648 0.2628 0.168 Uiso 1 1 calc R . .
H20C H 0.8912 1.4621 0.2655 0.168 Uiso 1 1 calc R . .
N1 N 0.90910(10) 1.01662(15) 0.03810(5) 0.0387(2) Uani 1 1 d . . .
N2 N 0.79200(11) 1.04949(18) 0.05086(6) 0.0482(3) Uani 1 1 d . . .
N3 N 0.79081(11) 1.1117(2) 0.09889(6) 0.0510(3) Uani 1 1 d . . .
C22 C 0.9878(4) 0.8584(4) 0.21263(17) 0.1191(12) Uani 1 1 d . . .
H22A H 0.9575 0.8055 0.1807 0.179 Uiso 1 1 calc R . .
H22B H 0.9847 0.7792 0.2417 0.179 Uiso 1 1 calc R . .
H22C H 1.0702 0.8937 0.2070 0.179 Uiso 1 1 calc R . .
B1 B 1.1042(3) 1.2770(5) 0.18885(16) 0.0954(10) Uani 1 1 d . . .
H1C H 1.1603 1.1922 0.1767 0.143 Uiso 1 1 calc R . .
H1D H 1.1218 1.3054 0.2254 0.143 Uiso 1 1 calc R . .
H1E H 1.1119 1.3764 0.1670 0.143 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
P1 C18 1.7878(15) . ?
P1 C21 1.808(2) . ?
P1 C19 1.816(2) . ?
P1 B1 1.908(3) . ?
C4 C5 1.388(2) . ?
C4 C3 1.3989(19) . ?
C4 N1 1.4257(18) . ?
C3 C8 1.395(3) . ?
C3 C2 1.498(3) . ?
C17 N1 1.3440(19) . ?
C17 C18 1.368(2) . ?
C17 H17 0.9300 . ?
C5 C6 1.384(2) . ?
C5 H5 0.9300 . ?
C8 C7 1.381(3) . ?
C8 H8 0.9300 . ?
C2 C1 1.565(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C11 C16 1.385(3) . ?
C11 C12 1.394(3) . ?
C11 C10 1.503(4) . ?
C7 C6 1.396(3) . ?
C7 H7 0.9300 . ?
C15 C16 1.378(3) . ?
C15 C14 1.410(3) . ?
C15 H15 0.9300 . ?
C18 N3 1.3615(19) . ?
C6 C9 1.508(3) . ?
C16 H16 0.9300 . ?
C13 C12 1.375(4) . ?
C13 C14 1.386(4) . ?
C13 H13 0.9300 . ?
C19 C20 1.512(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C14 C1 1.502(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C12 H12 0.9300 . ?
C9 C10 1.545(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C21 C22 1.509(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N1 N2 1.3536(17) . ?
N2 N3 1.2973(19) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
B1 H1C 0.9600 . ?
B1 H1D 0.9600 . ?
B1 H1E 0.9600 . ?

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
C18 P1 C21 104.30(9) . . ?
C18 P1 C19 103.80(8) . . ?
C21 P1 C19 106.11(13) . . ?
C18 P1 B1 112.23(13) . . ?
C21 P1 B1 114.96(15) . . ?
C19 P1 B1 114.35(15) . . ?
C5 C4 C3 122.22(14) . . ?
C5 C4 N1 117.80(12) . . ?
C3 C4 N1 119.55(14) . . ?
C8 C3 C4 115.00(17) . . ?
C8 C3 C2 119.31(15) . . ?
C4 C3 C2 123.99(16) . . ?
N1 C17 C18 105.20(12) . . ?
N1 C17 H17 127.4 . . ?
C18 C17 H17 127.4 . . ?
C6 C5 C4 120.26(15) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C8 C3 121.60(16) . . ?
C7 C8 H8 119.2 . . ?
C3 C8 H8 119.2 . . ?
C3 C2 C1 113.06(17) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C16 C11 C12 116.2(2) . . ?
C16 C11 C10 120.19(19) . . ?
C12 C11 C10 122.1(2) . . ?
C8 C7 C6 121.04(17) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
N3 C18 C17 107.86(13) . . ?
N3 C18 P1 122.93(12) . . ?
C17 C18 P1 129.14(11) . . ?
C5 C6 C7 116.82(18) . . ?
C5 C6 C9 120.64(17) . . ?
C7 C6 C9 121.25(18) . . ?
C15 C16 C11 121.56(18) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
C12 C13 C14 121.18(18) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C20 C19 P1 113.49(17) . . ?
C20 C19 H19A 108.9 . . ?
P1 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
P1 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C13 C14 C15 116.3(2) . . ?
C13 C14 C1 123.2(2) . . ?
C15 C14 C1 119.0(3) . . ?
C14 C1 C2 113.74(19) . . ?
C14 C1 H1A 108.8 . . ?
C2 C1 H1A 108.8 . . ?
C14 C1 H1B 108.8 . . ?
C2 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C13 C12 C11 121.2(2) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C6 C9 C10 112.94(19) . . ?
C6 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C6 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C22 C21 P1 113.1(2) . . ?
C22 C21 H21A 109.0 . . ?
P1 C21 H21A 109.0 . . ?
C22 C21 H21B 109.0 . . ?
P1 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C11 C10 C9 113.91(19) . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 N1 N2 110.15(12) . . ?
C17 N1 C4 128.71(12) . . ?
N2 N1 C4 121.13(11) . . ?
N3 N2 N1 107.47(12) . . ?
N2 N3 C18 109.33(13) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
P1 B1 H1C 109.5 . . ?
P1 B1 H1D 109.5 . . ?
H1C B1 H1D 109.5 . . ?
P1 B1 H1E 109.5 . . ?
H1C B1 H1E 109.5 . . ?
H1D B1 H1E 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        30.03
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 986150'
#######################################################################
#
#                 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_9

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (R)-1-Benzyl-4-(methyl-tert-butylphosphino-borane)-1H-1,2,3-triazole 
;
_chemical_name_common            ?
_chemical_melting_point          399
_chemical_formula_moiety         'C14 H23 B N3 P'
_chemical_formula_sum            'C14 H23 B N3 P'
_chemical_formula_weight         275.13
_chemical_absolute_configuration ad


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'
P P 0.1023 0.0942 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.8500(2)
_cell_length_b                   11.1410(2)
_cell_length_c                   14.4209(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1582.53(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9840
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      34.49

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32222
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         34.49
_reflns_number_total             6676
_reflns_number_gt                6142
_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0420P)²+0.1605P] 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   0.01(5)
_refine_ls_number_reflns         6676
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0832
_refine_ls_wR_factor_gt          0.0799
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
P1 P 0.82331(2) 0.58823(2) 0.849768(15) 0.01913(5) Uani 1 1 d . A .
C4 C 0.29682(9) 0.64143(8) 0.62578(6) 0.02171(16) Uani 1 1 d . . .
C1 C 0.65276(9) 0.57419(8) 0.80678(6) 0.01995(15) Uani 1 1 d . . .
C2 C 0.55972(10) 0.66183(9) 0.78448(7) 0.02295(17) Uani 1 1 d . . .
H2 H 0.5722 0.7464 0.7862 0.028 Uiso 1 1 calc R . .
C10 C 0.81020(10) 0.60682(10) 0.97687(7) 0.02760(18) Uani 1 1 d . . .
C3 C 0.31521(10) 0.64826(10) 0.72936(7) 0.02793(19) Uani 1 1 d . . .
H3A H 0.3070 0.7330 0.7493 0.034 Uiso 1 1 calc R . .
H3B H 0.2419 0.6021 0.7599 0.034 Uiso 1 1 calc R . .
C6 C 0.36161(13) 0.70723(10) 0.47280(8) 0.0325(2) Uani 1 1 d . . .
H6 H 0.4191 0.7536 0.4339 0.039 Uiso 1 1 calc R . .
C5 C 0.38109(11) 0.70894(10) 0.56818(7) 0.0287(2) Uani 1 1 d . . .
H5 H 0.4518 0.7561 0.5942 0.034 Uiso 1 1 calc R . .
C7 C 0.25955(12) 0.63884(11) 0.43409(8) 0.0326(2) Uani 1 1 d . . .
H7 H 0.2465 0.6382 0.3688 0.039 Uiso 1 1 calc R . .
C8 C 0.17652(12) 0.57133(12) 0.49084(8) 0.0360(2) Uani 1 1 d . . .
H8 H 0.1063 0.5240 0.4644 0.043 Uiso 1 1 calc R . .
C9 C 0.19498(10) 0.57211(10) 0.58671(7) 0.0298(2) Uani 1 1 d . . .
H9 H 0.1377 0.5251 0.6253 0.036 Uiso 1 1 calc R . .
C11A C 0.7950(3) 0.7494(2) 0.99094(16) 0.0338(5) Uani 0.563(5) 1 d P A 1
H11A H 0.7176 0.7786 0.9548 0.051 Uiso 0.563(5) 1 calc PR A 1
H11B H 0.8781 0.7895 0.9699 0.051 Uiso 0.563(5) 1 calc PR A 1
H11C H 0.7802 0.7670 1.0568 0.051 Uiso 0.563(5) 1 calc PR A 1
C12A C 0.9395(5) 0.5702(4) 1.0215(3) 0.0389(8) Uani 0.563(5) 1 d P A 1
H12A H 1.0160 0.6028 0.9861 0.058 Uiso 0.563(5) 1 calc PR A 1
H12B H 0.9454 0.4824 1.0227 0.058 Uiso 0.563(5) 1 calc PR A 1
H12C H 0.9424 0.6013 1.0850 0.058 Uiso 0.563(5) 1 calc PR A 1
C13A C 0.6861(3) 0.5494(3) 1.01815(15) 0.0399(7) Uani 0.563(5) 1 d P A 1
H13A H 0.6874 0.5597 1.0856 0.060 Uiso 0.563(5) 1 calc PR A 1
H13B H 0.6854 0.4636 1.0031 0.060 Uiso 0.563(5) 1 calc PR A 1
H13C H 0.6046 0.5875 0.9926 0.060 Uiso 0.563(5) 1 calc PR A 1
C11B C 0.7276(5) 0.7062(4) 1.0031(2) 0.0499(11) Uani 0.437(5) 1 d P A 2
H11D H 0.7276 0.7140 1.0708 0.075 Uiso 0.437(5) 1 calc PR A 2
H11E H 0.6345 0.6931 0.9812 0.075 Uiso 0.437(5) 1 calc PR A 2
H11F H 0.7638 0.7797 0.9753 0.075 Uiso 0.437(5) 1 calc PR A 2
C12B C 0.9571(6) 0.6106(5) 1.0160(4) 0.0373(10) Uani 0.437(5) 1 d P A 2
H12D H 1.0037 0.6822 0.9926 0.056 Uiso 0.437(5) 1 calc PR A 2
H12E H 1.0064 0.5386 0.9961 0.056 Uiso 0.437(5) 1 calc PR A 2
H12F H 0.9539 0.6133 1.0839 0.056 Uiso 0.437(5) 1 calc PR A 2
C13B C 0.7494(4) 0.4821(4) 1.0174(2) 0.0471(12) Uani 0.437(5) 1 d P A 2
H13D H 0.7561 0.4822 1.0852 0.071 Uiso 0.437(5) 1 calc PR A 2
H13E H 0.8014 0.4144 0.9924 0.071 Uiso 0.437(5) 1 calc PR A 2
H13F H 0.6540 0.4742 0.9991 0.071 Uiso 0.437(5) 1 calc PR A 2
C14 C 0.89369(13) 0.44222(11) 0.82811(10) 0.0397(3) Uani 1 1 d . . .
H14A H 0.8443 0.3822 0.8646 0.060 Uiso 1 1 calc R A .
H14B H 0.9897 0.4416 0.8460 0.060 Uiso 1 1 calc R . .
H14C H 0.8855 0.4232 0.7620 0.060 Uiso 1 1 calc R . .
B1 B 0.92125(14) 0.71391(16) 0.78889(10) 0.0399(3) Uani 1 1 d . . .
N3 N 0.44689(8) 0.60115(8) 0.75962(5) 0.02214(14) Uani 1 1 d . . .
N2 N 0.46741(9) 0.48172(8) 0.76436(6) 0.02572(16) Uani 1 1 d . . .
N1 N 0.59226(9) 0.46489(8) 0.79319(6) 0.02407(15) Uani 1 1 d . . .
H1A H 0.929(2) 0.6770(18) 0.7208(15) 0.070(6) Uiso 1 1 d . . .
H1B H 1.0202(19) 0.7227(17) 0.8288(13) 0.063(5) Uiso 1 1 d . . .
H1C H 0.8654(17) 0.7936(16) 0.7980(12) 0.049(5) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C14 1.7956(11) . ?
P1 C1 1.7974(9) . ?
P1 C10 1.8491(10) . ?
P1 B1 1.9137(14) . ?
C4 C9 1.3856(14) . ?
C4 C5 1.3945(14) . ?
C4 C3 1.5066(13) . ?
C1 N1 1.3699(12) . ?
C1 C2 1.3772(12) . ?
C2 N3 1.3494(13) . ?
C2 H2 0.9500 . ?
C10 C11B 1.425(3) . ?
C10 C12A 1.483(4) . ?
C10 C13A 1.502(2) . ?
C10 C12B 1.554(6) . ?
C10 C11A 1.608(2) . ?
C10 C13B 1.622(3) . ?
C3 N3 1.4656(12) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C6 C7 1.3795(17) . ?
C6 C5 1.3890(15) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C7 C8 1.3799(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.3945(15) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
B1 H1A 1.07(2) . ?
B1 H1B 1.136(19) . ?
B1 H1C 1.053(18) . ?
N3 N2 1.3476(12) . ?
N2 N1 1.3116(12) . ?

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
C14 P1 C1 102.83(5) . . ?
C14 P1 C10 107.51(6) . . ?
C1 P1 C10 106.64(4) . . ?
C14 P1 B1 112.86(8) . . ?
C1 P1 B1 112.12(5) . . ?
C10 P1 B1 114.08(6) . . ?
C9 C4 C5 119.30(9) . . ?
C9 C4 C3 121.22(9) . . ?
C5 C4 C3 119.45(9) . . ?
N1 C1 C2 107.90(8) . . ?
N1 C1 P1 122.23(7) . . ?
C2 C1 P1 129.85(7) . . ?
N3 C2 C1 104.77(8) . . ?
N3 C2 H2 127.6 . . ?
C1 C2 H2 127.6 . . ?
C11B C10 C12A 126.1(2) . . ?
C11B C10 C13A 76.2(2) . . ?
C12A C10 C13A 114.2(2) . . ?
C11B C10 C12B 114.5(3) . . ?
C12A C10 C12B 18.33(18) . . ?
C13A C10 C12B 128.7(2) . . ?
C11B C10 C11A 31.4(2) . . ?
C12A C10 C11A 107.23(18) . . ?
C13A C10 C11A 107.14(16) . . ?
C12B C10 C11A 90.8(2) . . ?
C11B C10 C13B 111.0(3) . . ?
C12A C10 C13B 85.7(2) . . ?
C13A C10 C13B 36.14(17) . . ?
C12B C10 C13B 103.7(2) . . ?
C11A C10 C13B 140.0(2) . . ?
C11B C10 P1 112.95(16) . . ?
C12A C10 P1 109.8(2) . . ?
C13A C10 P1 113.70(10) . . ?
C12B C10 P1 107.3(2) . . ?
C11A C10 P1 104.02(10) . . ?
C13B C10 P1 106.68(14) . . ?
N3 C3 C4 112.55(8) . . ?
N3 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
N3 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C7 C6 C5 120.59(10) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C5 C4 120.02(10) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C7 C8 119.54(10) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 120.48(10) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C4 C9 C8 120.06(10) . . ?
C4 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C11A H11A 109.5 . . ?
C10 C11A H11B 109.5 . . ?
C10 C11A H11C 109.5 . . ?
C10 C12A H12A 109.5 . . ?
C10 C12A H12B 109.5 . . ?
C10 C12A H12C 109.5 . . ?
C10 C13A H13A 109.5 . . ?
C10 C13A H13B 109.5 . . ?
C10 C13A H13C 109.5 . . ?
C10 C11B H11D 109.5 . . ?
C10 C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10 C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C10 C12B H12D 109.5 . . ?
C10 C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C10 C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C10 C13B H13D 109.5 . . ?
C10 C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C10 C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
P1 C14 H14A 109.5 . . ?
P1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
P1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
P1 B1 H1A 100.3(11) . . ?
P1 B1 H1B 105.2(10) . . ?
H1A B1 H1B 115.7(15) . . ?
P1 B1 H1C 107.2(9) . . ?
H1A B1 H1C 118.7(14) . . ?
H1B B1 H1C 108.2(13) . . ?
N2 N3 C2 110.95(8) . . ?
N2 N3 C3 120.09(8) . . ?
C2 N3 C3 128.95(9) . . ?
N1 N2 N3 107.33(8) . . ?
N2 N1 C1 109.04(8) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        34.49
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 986151'
#######################################################################
#
#                 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_10

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 Dichlorobis[1-benzyl-4-(di-tert-butylphosphino)-1H-1,2,3-triazole]palladium(II) 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H52 Cl2 N6 P2 Pd'
_chemical_formula_sum            'C34 H52 Cl2 N6 P2 Pd'
_chemical_formula_weight         784.06

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'
P P 0.1023 0.0942 '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'
Pd Pd -0.9988 1.0072 '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  '
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   10.2656(5)
_cell_length_b                   20.6740(10)
_cell_length_c                   9.0479(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.041(2)
_cell_angle_gamma                90.00
_cell_volume                     1890.83(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9812
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      35.52

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.38
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39732
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0156
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         29.13
_reflns_number_total             5081
_reflns_number_gt                4696
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0241P)²+0.7435P] 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         5081
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0196
_refine_ls_wR_factor_ref         0.0531
_refine_ls_wR_factor_gt          0.0508
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
Pd1 Pd 0.0000 0.5000 0.5000 0.01585(4) Uani 1 2 d S . .
P1 P 0.14204(3) 0.586600(13) 0.46027(3) 0.01529(6) Uani 1 1 d . . .
Cl1 Cl 0.14707(3) 0.427235(14) 0.43030(4) 0.02998(7) Uani 1 1 d . . .
C14 C 0.21223(11) 0.58478(6) 0.27961(13) 0.0210(2) Uani 1 1 d . . .
C10 C 0.27253(12) 0.59708(6) 0.63167(14) 0.0256(2) Uani 1 1 d . . .
C15 C 0.24968(14) 0.65303(6) 0.23224(15) 0.0287(3) Uani 1 1 d . . .
H15A H 0.3157 0.6719 0.3119 0.043 Uiso 1 1 calc R . .
H15B H 0.1706 0.6805 0.2152 0.043 Uiso 1 1 calc R . .
H15C H 0.2865 0.6501 0.1395 0.043 Uiso 1 1 calc R . .
C16 C 0.33417(13) 0.54091(6) 0.29005(16) 0.0287(3) Uani 1 1 d . . .
H16A H 0.3138 0.4982 0.3269 0.043 Uiso 1 1 calc R . .
H16B H 0.4081 0.5600 0.3594 0.043 Uiso 1 1 calc R . .
H16C H 0.3585 0.5365 0.1905 0.043 Uiso 1 1 calc R . .
C13 C 0.34226(15) 0.53194(8) 0.67187(17) 0.0387(3) Uani 1 1 d . . .
H13A H 0.3901 0.5192 0.5918 0.058 Uiso 1 1 calc R . .
H13B H 0.2763 0.4989 0.6830 0.058 Uiso 1 1 calc R . .
H13C H 0.4048 0.5363 0.7664 0.058 Uiso 1 1 calc R . .
C17 C 0.10099(13) 0.55831(7) 0.15865(14) 0.0288(3) Uani 1 1 d . . .
H17A H 0.1312 0.5572 0.0618 0.043 Uiso 1 1 calc R . .
H17B H 0.0232 0.5864 0.1511 0.043 Uiso 1 1 calc R . .
H17C H 0.0776 0.5145 0.1860 0.043 Uiso 1 1 calc R . .
C12 C 0.37658(14) 0.64854(8) 0.61518(17) 0.0367(3) Uani 1 1 d . . .
H12A H 0.3325 0.6898 0.5861 0.055 Uiso 1 1 calc R . .
H12B H 0.4268 0.6350 0.5378 0.055 Uiso 1 1 calc R . .
H12C H 0.4369 0.6537 0.7111 0.055 Uiso 1 1 calc R . .
C11 C 0.20045(15) 0.61587(8) 0.76069(15) 0.0368(3) Uani 1 1 d . . .
H11A H 0.2635 0.6159 0.8555 0.055 Uiso 1 1 calc R . .
H11B H 0.1299 0.5845 0.7667 0.055 Uiso 1 1 calc R . .
H11C H 0.1620 0.6591 0.7421 0.055 Uiso 1 1 calc R . .
C1 C 0.05510(11) 0.66313(5) 0.43772(12) 0.0174(2) Uani 1 1 d . . .
C2 C -0.06090(12) 0.67683(5) 0.34229(13) 0.0209(2) Uani 1 1 d . . .
H2 H -0.1171 0.6473 0.2810 0.025 Uiso 1 1 calc R . .
C4 C -0.26658(13) 0.81166(6) 0.37551(14) 0.0251(2) Uani 1 1 d . . .
C9 C -0.24164(15) 0.87432(7) 0.42671(16) 0.0323(3) Uani 1 1 d . . .
H9 H -0.1726 0.8985 0.3954 0.039 Uiso 1 1 calc R . .
C5 C -0.36943(15) 0.77748(8) 0.42008(18) 0.0373(3) Uani 1 1 d . . .
H5 H -0.3884 0.7347 0.3846 0.045 Uiso 1 1 calc R . .
C8 C -0.31693(18) 0.90189(8) 0.52347(18) 0.0440(4) Uani 1 1 d . . .
H8 H -0.2989 0.9448 0.5587 0.053 Uiso 1 1 calc R . .
C3 C -0.18267(14) 0.78186(6) 0.27253(14) 0.0297(3) Uani 1 1 d . . .
H3A H -0.2396 0.7557 0.1953 0.036 Uiso 1 1 calc R . .
H3B H -0.1422 0.8167 0.2206 0.036 Uiso 1 1 calc R . .
C7 C -0.41732(17) 0.86742(9) 0.5684(2) 0.0493(4) Uani 1 1 d . . .
H7 H -0.4680 0.8863 0.6356 0.059 Uiso 1 1 calc R . .
C6 C -0.44473(17) 0.80559(10) 0.5165(2) 0.0499(4) Uani 1 1 d . . .
H6 H -0.5152 0.7820 0.5465 0.060 Uiso 1 1 calc R . .
N3 N -0.07785(10) 0.74068(5) 0.35403(12) 0.0228(2) Uani 1 1 d . . .
N1 N 0.10257(12) 0.71980(5) 0.50317(14) 0.0327(3) Uani 1 1 d . . .
N2 N 0.02092(13) 0.76680(5) 0.45232(16) 0.0375(3) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 Cl1 2.2961(3) 3_566 ?
Pd1 Cl1 2.2961(3) . ?
Pd1 P1 2.3756(3) 3_566 ?
Pd1 P1 2.3756(3) . ?
P1 C1 1.8104(11) . ?
P1 C10 1.8767(12) . ?
P1 C14 1.8982(12) . ?
C14 C16 1.5354(17) . ?
C14 C17 1.5380(17) . ?
C14 C15 1.5427(16) . ?
C10 C12 1.5333(19) . ?
C10 C11 1.5371(19) . ?
C10 C13 1.5386(19) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C1 N1 1.3639(15) . ?
C1 C2 1.3730(16) . ?
C2 N3 1.3381(14) . ?
C2 H2 0.9500 . ?
C4 C9 1.3846(19) . ?
C4 C5 1.388(2) . ?
C4 C3 1.5066(18) . ?
C9 C8 1.387(2) . ?
C9 H9 0.9500 . ?
C5 C6 1.390(2) . ?
C5 H5 0.9500 . ?
C8 C7 1.372(3) . ?
C8 H8 0.9500 . ?
C3 N3 1.4661(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C7 C6 1.374(3) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
N3 N2 1.3402(15) . ?
N1 N2 1.3130(16) . ?

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
Cl1 Pd1 Cl1 180.0 3_566 . ?
Cl1 Pd1 P1 90.107(11) 3_566 3_566 ?
Cl1 Pd1 P1 89.892(11) . 3_566 ?
Cl1 Pd1 P1 89.894(11) 3_566 . ?
Cl1 Pd1 P1 90.107(11) . . ?
P1 Pd1 P1 180.0 3_566 . ?
C1 P1 C10 105.02(5) . . ?
C1 P1 C14 100.01(5) . . ?
C10 P1 C14 112.98(6) . . ?
C1 P1 Pd1 111.85(4) . . ?
C10 P1 Pd1 109.30(4) . . ?
C14 P1 Pd1 116.78(4) . . ?
C16 C14 C17 109.26(10) . . ?
C16 C14 C15 108.50(10) . . ?
C17 C14 C15 108.53(10) . . ?
C16 C14 P1 112.74(8) . . ?
C17 C14 P1 105.88(8) . . ?
C15 C14 P1 111.81(8) . . ?
C12 C10 C11 109.53(12) . . ?
C12 C10 C13 109.09(11) . . ?
C11 C10 C13 107.91(12) . . ?
C12 C10 P1 114.12(9) . . ?
C11 C10 P1 106.74(9) . . ?
C13 C10 P1 109.27(9) . . ?
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 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C1 C2 107.51(10) . . ?
N1 C1 P1 124.75(9) . . ?
C2 C1 P1 127.42(9) . . ?
N3 C2 C1 105.32(10) . . ?
N3 C2 H2 127.3 . . ?
C1 C2 H2 127.3 . . ?
C9 C4 C5 119.01(13) . . ?
C9 C4 C3 119.82(12) . . ?
C5 C4 C3 121.17(13) . . ?
C4 C9 C8 120.31(14) . . ?
C4 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C4 C5 C6 120.28(15) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C8 C9 120.25(16) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
N3 C3 C4 112.02(10) . . ?
N3 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
N3 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C8 C7 C6 120.11(15) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C6 C5 120.04(16) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C2 N3 N2 110.88(10) . . ?
C2 N3 C3 128.83(11) . . ?
N2 N3 C3 120.25(10) . . ?
N2 N1 C1 109.01(10) . . ?
N1 N2 N3 107.29(10) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        29.13
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 986152'
