#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:55:56 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180323 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/37/7153784.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_7153784
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         'C20 H18 B Br N3 P'
_chemical_formula_sum            'C20 H18 B Br N3 P'
_chemical_formula_weight         422.06
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 98.935(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.4175(3)
_cell_length_b                   15.1163(4)
_cell_length_c                   23.4211(7)
_cell_measurement_reflns_used    4905
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.52
_cell_volume                     3993.20(19)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            13208
_diffrn_reflns_theta_full        28.70
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    2.147
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         5129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0431P)²+3.8641P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.1037
_reflns_number_gt                3828
_reflns_number_total             5129
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00397g2.cif
_cod_data_source_block           2j
_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      'C 2/c'
_cod_database_code               7153784
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'
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
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
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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
