# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Nicolas Mezailles' _publ_contact_author_email NICOLAS.MEZAILLES@POLYTECHNIQUE.EDU _publ_section_title ; White Phosphorus as Single Source of "P" in the Synthesis of Nickel Phosphide ; loop_ _publ_author_name 'Nicolas Mezailles' 'Sophie Carenco' 'Xavier F LeGoff' 'Pascal LeFloch' 'Irene Resa' # Attachment 'chemcomm.cif' data_irg05007 _database_code_depnum_ccdc_archive 'CCDC 654636' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H66 Ni P2' _chemical_formula_sum 'C32 H66 Ni P2' _chemical_formula_weight 571.50 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' Ni Ni 0.3393 1.1124 '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 'C2/c ' 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 21.777(1) _cell_length_b 8.967(1) _cell_length_c 17.218(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.769(1) _cell_angle_gamma 90.00 _cell_volume 3361.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150.0(1) _cell_measurement_reflns_used 4592 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description Plate _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.129 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.690 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8197 _exptl_absorpt_correction_T_max 0.9469 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150.0(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15342 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 30.03 _reflns_number_total 4911 _reflns_number_gt 4007 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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/[\s^2^(Fo^2^)+(0.0476P)^2^+1.4756P] where P=(Fo^2^+2Fc^2^)/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 4911 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0995 _refine_ls_wR_factor_gt 0.0938 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 Ni1 Ni 0.0000 0.06734(3) 0.2500 0.02247(8) Uani 1 2 d S . . P1 P 0.041452(17) 0.21565(4) 0.16518(2) 0.02443(10) Uani 1 1 d . . . C1 C 0.01579(8) -0.22206(18) 0.16465(9) 0.0326(3) Uani 1 1 d . . . H1A H 0.0242 -0.2433 0.1094 0.039 Uiso 1 1 calc R . . H1B H -0.0036 -0.3119 0.1871 0.039 Uiso 1 1 calc R . . C2 C -0.02924(7) -0.09317(16) 0.16900(9) 0.0280(3) Uani 1 1 d . . . H2 H -0.0278 -0.0177 0.1304 0.034 Uiso 1 1 calc R . . C3 C -0.07236(7) -0.08134(16) 0.22718(9) 0.0279(3) Uani 1 1 d . . . H3 H -0.1000 0.0006 0.2259 0.033 Uiso 1 1 calc R . . C4 C 0.07731(7) -0.19304(17) 0.20757(9) 0.0316(3) Uani 1 1 d . . . H4A H 0.0929 -0.2885 0.2290 0.038 Uiso 1 1 calc R . . H4B H 0.1076 -0.1563 0.1698 0.038 Uiso 1 1 calc R . . C5 C 0.09470(7) 0.36444(17) 0.19730(9) 0.0285(3) Uani 1 1 d . . . H5A H 0.1049 0.4267 0.1517 0.034 Uiso 1 1 calc R . . H5B H 0.0731 0.4290 0.2348 0.034 Uiso 1 1 calc R . . C6 C 0.15457(7) 0.31099(18) 0.23508(9) 0.0305(3) Uani 1 1 d . . . H6A H 0.1449 0.2448 0.2793 0.037 Uiso 1 1 calc R . . H6B H 0.1779 0.2519 0.1969 0.037 Uiso 1 1 calc R . . C7 C 0.19434(8) 0.4390(2) 0.26396(11) 0.0392(4) Uani 1 1 d . . . H7A H 0.1703 0.5004 0.3005 0.047 Uiso 1 1 calc R . . H7B H 0.2052 0.5030 0.2193 0.047 Uiso 1 1 calc R . . C8 C 0.25296(9) 0.3875(3) 0.30449(12) 0.0501(5) Uani 1 1 d . . . H8A H 0.2426 0.3251 0.3492 0.075 Uiso 1 1 calc R . . H8B H 0.2764 0.4745 0.3224 0.075 Uiso 1 1 calc R . . H8C H 0.2777 0.3297 0.2681 0.075 Uiso 1 1 calc R . . C9 C 0.08713(7) 0.12337(17) 0.08925(8) 0.0286(3) Uani 1 1 d . . . H9A H 0.1205 0.0676 0.1158 0.034 Uiso 1 1 calc R . . H9B H 0.0603 0.0487 0.0635 0.034 Uiso 1 1 calc R . . C10 C 0.11638(8) 0.21700(18) 0.02537(9) 0.0329(3) Uani 1 1 d . . . H10A H 0.0836 0.2579 -0.0089 0.040 Uiso 1 1 calc R . . H10B H 0.1386 0.3020 0.0493 0.040 Uiso 1 1 calc R . . C11 C 0.16084(8) 0.1266(2) -0.02312(9) 0.0347(3) Uani 1 1 d . . . H11A H 0.1385 0.0419 -0.0473 0.042 Uiso 1 1 calc R . . H11B H 0.1933 0.0850 0.0113 0.042 Uiso 1 1 calc R . . C12 C 0.19068(9) 0.2190(2) -0.08667(11) 0.0482(5) Uani 1 1 d . . . H12A H 0.1592 0.2513 -0.1242 0.072 Uiso 1 1 calc R . . H12B H 0.2214 0.1584 -0.1132 0.072 Uiso 1 1 calc R . . H12C H 0.2106 0.3066 -0.0635 0.072 Uiso 1 1 calc R . . C13 C -0.01074(7) 0.33623(17) 0.10735(9) 0.0293(3) Uani 1 1 d . . . H13A H -0.0266 0.4151 0.1420 0.035 Uiso 1 1 calc R . . H13B H 0.0137 0.3861 0.0668 0.035 Uiso 1 1 calc R . . C14 C -0.06529(7) 0.26043(17) 0.06787(8) 0.0282(3) Uani 1 1 d . . . H14A H -0.0889 0.2049 0.1071 0.034 Uiso 1 1 calc R . . H14B H -0.0502 0.1878 0.0293 0.034 Uiso 1 1 calc R . . C15 C -0.10735(7) 0.37254(19) 0.02731(9) 0.0349(3) Uani 1 1 d . . . H15A H -0.1206 0.4477 0.0658 0.042 Uiso 1 1 calc R . . H15B H -0.0837 0.4252 -0.0130 0.042 Uiso 1 1 calc R . . C16 C -0.16409(8) 0.3037(2) -0.01051(11) 0.0464(4) Uani 1 1 d . . . H16A H -0.1516 0.2309 -0.0497 0.070 Uiso 1 1 calc R . . H16B H -0.1887 0.3822 -0.0354 0.070 Uiso 1 1 calc R . . H16C H -0.1885 0.2538 0.0291 0.070 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 Ni1 0.02320(13) 0.01633(13) 0.02784(14) 0.000 -0.00070(9) 0.000 P1 0.02497(18) 0.01842(18) 0.02985(19) 0.00089(13) -0.00135(14) -0.00182(13) C1 0.0386(8) 0.0240(8) 0.0353(8) -0.0042(6) 0.0026(6) -0.0007(6) C2 0.0320(7) 0.0194(7) 0.0326(7) -0.0020(5) -0.0032(6) -0.0035(6) C3 0.0264(7) 0.0200(7) 0.0373(8) -0.0027(6) -0.0033(6) -0.0029(5) C4 0.0323(8) 0.0218(7) 0.0409(8) 0.0013(6) 0.0052(6) 0.0049(6) C5 0.0293(7) 0.0215(7) 0.0347(7) -0.0010(6) -0.0010(6) -0.0044(6) C6 0.0288(7) 0.0282(8) 0.0345(8) 0.0003(6) -0.0009(6) -0.0044(6) C7 0.0324(8) 0.0381(10) 0.0470(9) -0.0083(7) -0.0057(7) -0.0064(7) C8 0.0366(9) 0.0618(13) 0.0518(10) -0.0039(10) -0.0105(8) -0.0088(9) C9 0.0313(7) 0.0245(7) 0.0299(7) 0.0020(6) 0.0017(6) -0.0025(6) C10 0.0385(8) 0.0284(8) 0.0319(7) 0.0025(6) 0.0009(6) -0.0055(6) C11 0.0343(8) 0.0371(9) 0.0328(7) 0.0000(7) 0.0018(6) -0.0058(7) C12 0.0492(11) 0.0579(13) 0.0377(9) -0.0003(8) 0.0077(8) -0.0167(9) C13 0.0301(7) 0.0207(7) 0.0371(7) 0.0041(6) -0.0021(6) -0.0015(6) C14 0.0290(7) 0.0258(7) 0.0296(7) 0.0023(6) -0.0004(6) 0.0000(6) C15 0.0333(8) 0.0321(8) 0.0391(8) 0.0042(7) -0.0044(6) 0.0038(7) C16 0.0359(9) 0.0518(12) 0.0510(10) 0.0016(9) -0.0106(8) 0.0031(8) _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 Ni1 C2 2.0971(14) . ? Ni1 C2 2.0971(14) 2 ? Ni1 C3 2.0973(14) . ? Ni1 C3 2.0973(14) 2 ? Ni1 P1 2.1799(4) 2 ? Ni1 P1 2.1799(4) . ? P1 C5 1.8475(15) . ? P1 C9 1.8488(15) . ? P1 C13 1.8498(15) . ? C1 C2 1.518(2) . ? C1 C4 1.543(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.386(2) . ? C2 H2 0.9500 . ? C3 C4 1.510(2) 2 ? C3 H3 0.9500 . ? C4 C3 1.510(2) 2 ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.526(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.518(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.519(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.529(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.521(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.525(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.521(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.523(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.520(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 Ni1 C2 93.32(8) . 2 ? C2 Ni1 C3 38.60(6) . . ? C2 Ni1 C3 84.78(6) 2 . ? C2 Ni1 C3 84.78(6) . 2 ? C2 Ni1 C3 38.60(6) 2 2 ? C3 Ni1 C3 101.06(8) . 2 ? C2 Ni1 P1 137.69(4) . 2 ? C2 Ni1 P1 95.62(4) 2 2 ? C3 Ni1 P1 101.33(4) . 2 ? C3 Ni1 P1 125.39(4) 2 2 ? C2 Ni1 P1 95.62(4) . . ? C2 Ni1 P1 137.69(4) 2 . ? C3 Ni1 P1 125.39(4) . . ? C3 Ni1 P1 101.33(4) 2 . ? P1 Ni1 P1 104.81(2) 2 . ? C5 P1 C9 101.15(7) . . ? C5 P1 C13 96.76(7) . . ? C9 P1 C13 102.33(7) . . ? C5 P1 Ni1 120.26(5) . . ? C9 P1 Ni1 115.61(5) . . ? C13 P1 Ni1 117.40(5) . . ? C2 C1 C4 113.89(12) . . ? C2 C1 H1A 108.8 . . ? C4 C1 H1A 108.8 . . ? C2 C1 H1B 108.8 . . ? C4 C1 H1B 108.8 . . ? H1A C1 H1B 107.7 . . ? C3 C2 C1 122.57(14) . . ? C3 C2 Ni1 70.70(8) . . ? C1 C2 Ni1 111.40(10) . . ? C3 C2 H2 118.7 . . ? C1 C2 H2 118.7 . . ? Ni1 C2 H2 88.0 . . ? C2 C3 C4 122.86(14) . 2 ? C2 C3 Ni1 70.69(8) . . ? C4 C3 Ni1 110.07(10) 2 . ? C2 C3 H3 118.6 . . ? C4 C3 H3 118.6 2 . ? Ni1 C3 H3 89.2 . . ? C3 C4 C1 113.45(12) 2 . ? C3 C4 H4A 108.9 2 . ? C1 C4 H4A 108.9 . . ? C3 C4 H4B 108.9 2 . ? C1 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C6 C5 P1 115.46(11) . . ? C6 C5 H5A 108.4 . . ? P1 C5 H5A 108.4 . . ? C6 C5 H5B 108.4 . . ? P1 C5 H5B 108.4 . . ? H5A C5 H5B 107.5 . . ? C7 C6 C5 112.48(13) . . ? C7 C6 H6A 109.1 . . ? C5 C6 H6A 109.1 . . ? C7 C6 H6B 109.1 . . ? C5 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? C6 C7 C8 113.12(16) . . ? C6 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? C6 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 P1 119.74(11) . . ? C10 C9 H9A 107.4 . . ? P1 C9 H9A 107.4 . . ? C10 C9 H9B 107.4 . . ? P1 C9 H9B 107.4 . . ? H9A C9 H9B 106.9 . . ? C11 C10 C9 112.12(13) . . ? C11 C10 H10A 109.2 . . ? C9 C10 H10A 109.2 . . ? C11 C10 H10B 109.2 . . ? C9 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? C10 C11 C12 112.64(15) . . ? C10 C11 H11A 109.1 . . ? C12 C11 H11A 109.1 . . ? C10 C11 H11B 109.1 . . ? C12 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? 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 . . ? C14 C13 P1 116.74(10) . . ? C14 C13 H13A 108.1 . . ? P1 C13 H13A 108.1 . . ? C14 C13 H13B 108.1 . . ? P1 C13 H13B 108.1 . . ? H13A C13 H13B 107.3 . . ? C13 C14 C15 111.79(13) . . ? C13 C14 H14A 109.3 . . ? C15 C14 H14A 109.3 . . ? C13 C14 H14B 109.3 . . ? C15 C14 H14B 109.3 . . ? H14A C14 H14B 107.9 . . ? C16 C15 C14 114.14(15) . . ? C16 C15 H15A 108.7 . . ? C14 C15 H15A 108.7 . . ? C16 C15 H15B 108.7 . . ? C14 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.514 _refine_diff_density_min -0.470 _refine_diff_density_rms 0.057