#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:55:56 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180323 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/37/7153780.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7153780
loop_
_publ_author_name
'Veillard, Romain'
'Bernoud, Elise'
'Abdellah, Ibrahim'
'Lohier, Jean-François'
'Alayrac, Carole'
'Gaumont, Annie-Claude'
_publ_section_title
;
 Silyl alkynylphosphine-boranes: key precursors of triazolylphosphines via
 tandem desilylation-Click chemistry.
;
_journal_issue                   22
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3635
_journal_page_last               3640
_journal_paper_doi               10.1039/c4ob00397g
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C21 H18 N3 P'
_chemical_formula_sum            'C21 H18 N3 P'
_chemical_formula_weight         343.35
_chemical_melting_point          371
_chemical_name_systematic
; 
1-Benzyl-4-(diphenylphosphino)-1H-1,2,3-triazole 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.415(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0928(3)
_cell_length_b                   10.6178(3)
_cell_length_c                   17.3125(5)
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.80
_cell_volume                     1835.29(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            43181
_diffrn_reflns_theta_full        28.71
_diffrn_reflns_theta_max         28.71
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0478P)²+0.3360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1050
_reflns_number_gt                3603
_reflns_number_total             4717
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00397g2.cif
_cod_data_source_block           1i
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 7153779--7153787.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7153780
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'
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
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
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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)
