#------------------------------------------------------------------------------
#$Date: 2016-03-25 16:19:32 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179963 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/57/7025712.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_7025712
loop_
_publ_author_name
'Choong, Sam L.'
'Jones, Cameron'
'Stasch, Andreas'
_publ_section_title
;
 Using "click" chemistry to access a new class of tripodal
 P3-ligand containing P=C bonds.
;
_journal_issue                   25
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5774
_journal_page_last               5776
_journal_paper_doi               10.1039/c002940h
_journal_volume                  39
_journal_year                    2010
_chemical_formula_sum            'C18 H24 N9 P3'
_chemical_formula_weight         459.37
_chemical_name_systematic
;
?
;
_space_group_IT_number           148
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   17.456(3)
_cell_length_b                   17.456(3)
_cell_length_c                   12.415(3)
_cell_measurement_temperature    123(2)
_cell_volume                     3276.2(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_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  0.0548
_diffrn_reflns_av_sigmaI/netI    0.0752
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2982
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         3.16
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav (Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0492
_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)+(0.0626P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1311
_reflns_number_gt                1048
_reflns_number_total             1586
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c002940h.txt
_cod_data_source_block           compound4
_cod_original_cell_volume        3276.2(9)
_cod_original_sg_symbol_H-M      R-3
_cod_database_code               7025712
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
P1 P 0.48199(4) 0.81988(5) 0.04234(6) 0.0344(3) Uani 1 1 d .
N1 N 0.54622(12) 0.83217(12) -0.06637(16) 0.0270(5) Uani 1 1 d .
C1 C 0.42182(14) 0.73489(14) -0.18349(18) 0.0224(5) Uani 1 1 d .
N2 N 0.63367(13) 0.87651(14) -0.04878(19) 0.0357(6) Uani 1 1 d .
C2 C 0.40185(14) 0.64612(15) -0.18384(18) 0.0222(5) Uani 1 1 d .
N3 N 0.65213(14) 0.90207(14) 0.05178(18) 0.0355(6) Uani 1 1 d .
C3 C 0.51760(14) 0.80737(15) -0.17964(18) 0.0257(6) Uani 1 1 d .
H3A H 0.5550 0.7867 -0.2147 0.031 Uiso 1 1 calc R
H3B H 0.5250 0.8597 -0.2196 0.031 Uiso 1 1 calc R
C4 C 0.47662(15) 0.62604(16) -0.1826(2) 0.0283(6) Uani 1 1 d .
H4A H 0.4527 0.5627 -0.1698 0.043 Uiso 1 1 calc R
H4B H 0.5183 0.6600 -0.1251 0.043 Uiso 1 1 calc R
H4C H 0.5073 0.6424 -0.2521 0.043 Uiso 1 1 calc R
C5 C 0.57951(16) 0.87912(16) 0.1127(2) 0.0334(6) Uani 1 1 d .
C6 C 0.59193(18) 0.90748(19) 0.2280(2) 0.0427(7) Uani 1 1 d .
H6A H 0.6258 0.8845 0.2652 0.064 Uiso 1 1 calc R
H6B H 0.5340 0.8843 0.2625 0.064 Uiso 1 1 calc R
H6C H 0.6241 0.9722 0.2318 0.064 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0238(4) 0.0409(5) 0.0321(4) -0.0025(3) -0.0008(3) 0.0115(3)
N1 0.0204(11) 0.0218(10) 0.0363(13) -0.0009(9) -0.0011(9) 0.0086(9)
C1 0.0236(12) 0.0223(13) 0.0192(12) 0.0010(9) 0.0034(9) 0.0100(10)
N2 0.0217(11) 0.0350(13) 0.0491(15) -0.0012(11) -0.0016(10) 0.0131(10)
C2 0.0264(13) 0.0249(13) 0.0174(12) 0.0013(9) 0.0028(9) 0.0143(10)
N3 0.0287(12) 0.0338(13) 0.0436(14) -0.0034(11) -0.0063(11) 0.0153(10)
C3 0.0234(12) 0.0235(13) 0.0283(13) 0.0062(10) 0.0069(11) 0.0103(11)
C4 0.0263(13) 0.0281(13) 0.0324(14) -0.0029(11) 0.0037(11) 0.0149(11)
C5 0.0298(14) 0.0264(14) 0.0425(16) 0.0027(12) -0.0042(12) 0.0129(12)
C6 0.0396(16) 0.0407(17) 0.0391(18) -0.0045(13) -0.0078(13) 0.0136(14)
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
_geom_angle_site_symmetry_1
N1 P1 C5 86.30(12) .
N2 N1 C3 116.33(19) .
N2 N1 P1 115.65(16) .
C3 N1 P1 127.74(15) .
C2 C1 C2 120.6(2) 2_665
C2 C1 C3 120.5(2) 2_665
C2 C1 C3 118.9(2) .
N3 N2 N1 111.5(2) .
C1 C2 C1 119.4(2) 3_565
C1 C2 C4 121.4(2) 3_565
C1 C2 C4 119.2(2) .
N2 N3 C5 113.4(2) .
N1 C3 C1 110.16(18) .
N1 C3 H3A 109.6 .
C1 C3 H3A 109.6 .
N1 C3 H3B 109.6 .
C1 C3 H3B 109.6 .
H3A C3 H3B 108.1 .
C2 C4 H4A 109.5 .
C2 C4 H4B 109.5 .
H4A C4 H4B 109.5 .
C2 C4 H4C 109.5 .
H4A C4 H4C 109.5 .
H4B C4 H4C 109.5 .
N3 C5 C6 118.6(2) .
N3 C5 P1 113.1(2) .
C6 C5 P1 128.4(2) .
C5 C6 H6A 109.5 .
C5 C6 H6B 109.5 .
H6A C6 H6B 109.5 .
C5 C6 H6C 109.5 .
H6A C6 H6C 109.5 .
H6B C6 H6C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 N1 1.698(2) .
P1 C5 1.723(3) .
N1 N2 1.340(3) .
N1 C3 1.483(3) .
C1 C2 1.404(3) 2_665
C1 C2 1.408(3) .
C1 C3 1.511(3) .
N2 N3 1.311(3) .
C2 C1 1.404(3) 3_565
C2 C4 1.511(3) .
N3 C5 1.353(3) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 C6 1.494(4) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
