# Electronic Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_bors41 #TrackingRef 'web_deposit_cif_file_0_Boris_1363101981.BORS41.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H33 Cl Ni O3 P2' _chemical_formula_sum 'C19 H33 Cl Ni O3 P2' _chemical_formula_weight 465.55 _chemical_compound_source 'Synthesized by the authors. See text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni -3.0029 0.5091 '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 _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 18.8143(2) _cell_length_b 18.2714(2) _cell_length_c 14.9031(2) _cell_angle_alpha 90 _cell_angle_beta 117.8053(4) _cell_angle_gamma 90 _cell_volume 4531.62(9) _cell_formula_units_Z 8 _cell_measurement_temperature 100 _cell_measurement_reflns_used 19044 _cell_measurement_theta_min 5.89 _cell_measurement_theta_max 70.75 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1968 _exptl_absorpt_coefficient_mu 3.778 _exptl_absorpt_correction_Type multi-scan _exptl_absorpt_correction_T_min 0.7451 _exptl_absorpt_correction_T_max 0.8597 _exptl_absorpt_process_details 'Sadabs (Sheldrick, 2008)' _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker smart diffractometer equiped with an APEX II CCD Detector, a graphite monochromator. The crystal-to-detector distance was 5.0 cm, and the data collection was carried out in 512 x 512 pixel mode. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 10.0 degree scan in 33 frames over four different parts of the reciprocal space (132 frames total). ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Incoatec I\muS Microsource ' _diffrn_radiation_monochromator 'Quazar MX' _diffrn_measurement_device_type 'Bruker APEX II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.3 _diffrn_reflns_number 46267 _diffrn_reflns_av_R_equivalents 0.026 _diffrn_reflns_av_sigmaI/netI 0.0124 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 71.18 _reflns_number_total 4365 _reflns_number_gt 4150 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker AXS, 2009)' _computing_cell_refinement 'SAINT V7.68A(Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A(Bruker AXS, 2009)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'UdMX (Maris, 2004)' _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^)+(0.1000P)^2^] 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 4365 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0265 _refine_ls_R_factor_gt 0.0253 _refine_ls_wR_factor_ref 0.0984 _refine_ls_wR_factor_gt 0.0951 _refine_ls_goodness_of_fit_ref 0.918 _refine_ls_restrained_S_all 0.918 _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 C1 C 0.30806(7) 0.94552(6) 0.68628(9) 0.0151(2) Uani 1 1 d . . . C2 C 0.38541(7) 0.97320(6) 0.74183(9) 0.0158(2) Uani 1 1 d . . . C3 C 0.45032(7) 0.93268(6) 0.81209(9) 0.0167(2) Uani 1 1 d . . . H3 H 0.5018 0.9543 0.8498 0.020 Uiso 1 1 calc R . . C4 C 0.43712(7) 0.85951(7) 0.82507(9) 0.0183(2) Uani 1 1 d . . . C5 C 0.36079(7) 0.82786(6) 0.77109(9) 0.0188(2) Uani 1 1 d . . . H5 H 0.3520 0.7778 0.7801 0.023 Uiso 1 1 calc R . . C6 C 0.29865(7) 0.87170(6) 0.70433(9) 0.0165(2) Uani 1 1 d . . . C7 C 0.57350(8) 0.84632(8) 0.94936(13) 0.0337(3) Uani 1 1 d . . . H7A H 0.5937 0.8654 0.9041 0.051 Uiso 1 1 calc R . . H7B H 0.6108 0.8094 0.9946 0.051 Uiso 1 1 calc R . . H7C H 0.5688 0.8865 0.9899 0.051 Uiso 1 1 calc R . . C11 C 0.10103(8) 0.85751(7) 0.46178(10) 0.0226(3) Uani 1 1 d . . . H11 H 0.0864 0.8079 0.4765 0.027 Uiso 1 1 calc R . . C12 C 0.15591(9) 0.84683(9) 0.41294(11) 0.0358(3) Uani 1 1 d . . . H12A H 0.1276 0.8183 0.3504 0.054 Uiso 1 1 calc R . . H12B H 0.2046 0.8206 0.4601 0.054 Uiso 1 1 calc R . . H12C H 0.1707 0.8947 0.3970 0.054 Uiso 1 1 calc R . . C13 C 0.02290(8) 0.89703(8) 0.39095(10) 0.0289(3) Uani 1 1 d . . . H13A H 0.0355 0.9455 0.3741 0.043 Uiso 1 1 calc R . . H13B H -0.0107 0.9023 0.4248 0.043 Uiso 1 1 calc R . . H13C H -0.0061 0.8685 0.3286 0.043 Uiso 1 1 calc R . . C14 C 0.08737(7) 0.90884(6) 0.63860(9) 0.0179(2) Uani 1 1 d . . . H14 H 0.0411 0.9409 0.5945 0.021 Uiso 1 1 calc R . . C15 C 0.05287(8) 0.83390(7) 0.64324(11) 0.0276(3) Uani 1 1 d . . . H15A H 0.0970 0.7994 0.6799 0.041 Uiso 1 1 calc R . . H15B H 0.0192 0.8159 0.5742 0.041 Uiso 1 1 calc R . . H15C H 0.0203 0.8384 0.6786 0.041 Uiso 1 1 calc R . . C16 C 0.12966(9) 0.94496(9) 0.74280(10) 0.0300(3) Uani 1 1 d . . . H16A H 0.0927 0.9476 0.7721 0.045 Uiso 1 1 calc R . . H16B H 0.1466 0.9945 0.7359 0.045 Uiso 1 1 calc R . . H16C H 0.1769 0.9160 0.7873 0.045 Uiso 1 1 calc R . . C21 C 0.34370(7) 1.11414(6) 0.54161(9) 0.0181(2) Uani 1 1 d . . . H21 H 0.3000 1.1473 0.4942 0.022 Uiso 1 1 calc R . . C22 C 0.34531(8) 1.04751(7) 0.47963(9) 0.0227(3) Uani 1 1 d . . . H22A H 0.3518 1.0641 0.4214 0.034 Uiso 1 1 calc R . . H22B H 0.2948 1.0203 0.4556 0.034 Uiso 1 1 calc R . . H22C H 0.3903 1.0156 0.5224 0.034 Uiso 1 1 calc R . . C23 C 0.42252(8) 1.15744(7) 0.58411(11) 0.0270(3) Uani 1 1 d . . . H23A H 0.4670 1.1261 0.6300 0.040 Uiso 1 1 calc R . . H23B H 0.4187 1.2002 0.6214 0.040 Uiso 1 1 calc R . . H23C H 0.4322 1.1737 0.5281 0.040 Uiso 1 1 calc R . . C24 C 0.31278(7) 1.16612(6) 0.70694(9) 0.0181(2) Uani 1 1 d . . . H24 H 0.3692 1.1832 0.7500 0.022 Uiso 1 1 calc R . . C25 C 0.27716(9) 1.14539(7) 0.77750(10) 0.0267(3) Uani 1 1 d . . . H25A H 0.2824 1.1868 0.8219 0.040 Uiso 1 1 calc R . . H25B H 0.3061 1.1031 0.8188 0.040 Uiso 1 1 calc R . . H25C H 0.2202 1.1330 0.7368 0.040 Uiso 1 1 calc R . . C26 C 0.26554(8) 1.22897(7) 0.63601(9) 0.0223(3) Uani 1 1 d . . . H26A H 0.2106 1.2127 0.5908 0.033 Uiso 1 1 calc R . . H26B H 0.2919 1.2437 0.5955 0.033 Uiso 1 1 calc R . . H26C H 0.2639 1.2707 0.6764 0.033 Uiso 1 1 calc R . . Cl1 Cl 0.126675(17) 1.075985(15) 0.49155(2) 0.02238(11) Uani 1 1 d . . . Ni1 Ni 0.222795(12) 1.003806(10) 0.595003(15) 0.01384(10) Uani 1 1 d . . . O1 O 0.22182(5) 0.84237(4) 0.65177(7) 0.01923(19) Uani 1 1 d . . . O2 O 0.39950(5) 1.04528(4) 0.72550(7) 0.01789(19) Uani 1 1 d . . . O3 O 0.49637(5) 0.81379(5) 0.89041(7) 0.0240(2) Uani 1 1 d . . . P1 P 0.154929(17) 0.905657(15) 0.58228(2) 0.01477(11) Uani 1 1 d . . . P2 P 0.316321(17) 1.084461(15) 0.63844(2) 0.01401(11) Uani 1 1 d . . . 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 C1 0.0146(6) 0.0149(5) 0.0174(5) 0.0023(4) 0.0088(4) 0.0014(4) C2 0.0190(6) 0.0129(5) 0.0181(5) 0.0015(4) 0.0110(5) -0.0004(4) C3 0.0135(5) 0.0174(6) 0.0194(5) 0.0014(4) 0.0078(4) 0.0002(4) C4 0.0175(6) 0.0171(6) 0.0210(6) 0.0049(4) 0.0097(5) 0.0046(4) C5 0.0206(6) 0.0139(5) 0.0243(6) 0.0028(4) 0.0125(5) 0.0005(4) C6 0.0159(5) 0.0160(5) 0.0199(6) -0.0001(4) 0.0102(5) -0.0010(4) C7 0.0195(6) 0.0223(6) 0.0425(9) 0.0077(6) 0.0005(6) 0.0004(5) C11 0.0247(6) 0.0216(6) 0.0211(6) -0.0053(5) 0.0105(5) -0.0032(5) C12 0.0391(8) 0.0428(8) 0.0305(8) -0.0090(6) 0.0205(7) 0.0039(6) C13 0.0268(7) 0.0361(7) 0.0175(6) -0.0043(5) 0.0051(5) -0.0025(5) C14 0.0149(6) 0.0210(6) 0.0186(6) 0.0027(4) 0.0086(5) 0.0005(4) C15 0.0219(6) 0.0267(7) 0.0366(7) 0.0115(6) 0.0157(6) 0.0005(5) C16 0.0312(7) 0.0411(8) 0.0214(6) -0.0026(6) 0.0153(6) -0.0024(6) C21 0.0199(6) 0.0160(5) 0.0212(6) 0.0043(4) 0.0119(5) 0.0022(4) C22 0.0276(6) 0.0215(6) 0.0231(6) 0.0016(5) 0.0152(5) 0.0034(5) C23 0.0259(7) 0.0261(7) 0.0339(7) 0.0009(5) 0.0182(6) -0.0065(5) C24 0.0200(6) 0.0148(5) 0.0180(6) -0.0012(4) 0.0075(5) -0.0001(4) C25 0.0382(7) 0.0250(6) 0.0212(6) -0.0004(5) 0.0174(6) 0.0013(5) C26 0.0260(6) 0.0171(6) 0.0228(6) 0.0007(5) 0.0105(5) 0.0037(4) Cl1 0.01637(18) 0.02208(18) 0.02355(18) 0.00538(11) 0.00501(14) 0.00359(10) Ni1 0.01278(15) 0.01265(15) 0.01576(16) 0.00152(7) 0.00638(11) 0.00009(6) O1 0.0147(4) 0.0139(4) 0.0269(5) 0.0026(3) 0.0078(4) -0.0011(3) O2 0.0139(4) 0.0138(4) 0.0230(4) 0.0042(3) 0.0062(3) -0.0005(3) O3 0.0170(4) 0.0169(4) 0.0304(5) 0.0071(4) 0.0047(4) 0.0023(3) P1 0.01398(17) 0.01389(17) 0.01643(18) 0.00035(10) 0.00707(14) -0.00095(9) P2 0.01358(18) 0.01190(17) 0.01614(18) 0.00164(9) 0.00660(14) 0.00033(9) _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_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 . . 1.3911(16) y C1 C6 . . 1.4025(16) y C1 Ni1 . . 1.8768(11) y C2 O2 . . 1.3871(14) y C2 C3 . . 1.3939(16) y C3 C4 . . 1.3896(17) y C3 H3 . . 0.9500 ? C4 O3 . . 1.3697(14) y C4 C5 . . 1.4023(17) y C5 C6 . . 1.3832(17) y C5 H5 . . 0.9500 ? C6 O1 . . 1.3907(14) y C7 O3 . . 1.4289(16) y C7 H7a . . 0.9800 ? C7 H7b . . 0.9800 ? C7 H7c . . 0.9800 ? C11 C12 . . 1.5281(19) y C11 C13 . . 1.5326(18) y C11 P1 . . 1.8244(12) y C11 H11 . . 1.0000 ? C12 H12a . . 0.9800 ? C12 H12b . . 0.9800 ? C12 H12c . . 0.9800 ? C13 H13a . . 0.9800 ? C13 H13b . . 0.9800 ? C13 H13c . . 0.9800 ? C14 C16 . . 1.5256(18) y C14 C15 . . 1.5307(17) y C14 P1 . . 1.8217(12) y C14 H14 . . 1.0000 ? C15 H15a . . 0.9800 ? C15 H15b . . 0.9800 ? C15 H15c . . 0.9800 ? C16 H16a . . 0.9800 ? C16 H16b . . 0.9800 ? C16 H16c . . 0.9800 ? C21 C23 . . 1.5330(17) y C21 C22 . . 1.5369(16) y C21 P2 . . 1.8263(12) y C21 H21 . . 1.0000 ? C22 H22a . . 0.9800 ? C22 H22b . . 0.9800 ? C22 H22c . . 0.9800 ? C23 H23a . . 0.9800 ? C23 H23b . . 0.9800 ? C23 H23c . . 0.9800 ? C24 C26 . . 1.5329(16) y C24 C25 . . 1.5349(17) y C24 P2 . . 1.8264(12) y C24 H24 . . 1.0000 ? C25 H25a . . 0.9800 ? C25 H25b . . 0.9800 ? C25 H25c . . 0.9800 ? C26 H26a . . 0.9800 ? C26 H26b . . 0.9800 ? C26 H26c . . 0.9800 ? Cl1 Ni1 . . 2.1876(3) y Ni1 P2 . . 2.1504(3) y Ni1 P1 . . 2.1579(3) y O1 P1 . . 1.6666(8) y O2 P2 . . 1.6586(8) y loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 C1 C6 . . . 115.22(10) y C2 C1 NI1 . . . 121.89(9) y C6 C1 NI1 . . . 122.89(9) y O2 C2 C1 . . . 118.25(10) y O2 C2 C3 . . . 117.64(10) y C1 C2 C3 . . . 124.10(11) y C4 C3 C2 . . . 117.70(11) y C4 C3 H3 . . . 121.2 ? C2 C3 H3 . . . 121.2 ? O3 C4 C3 . . . 123.15(11) y O3 C4 C5 . . . 115.62(10) y C3 C4 C5 . . . 121.24(11) y C6 C5 C4 . . . 118.01(11) y C6 C5 H5 . . . 121.0 ? C4 C5 H5 . . . 121.0 ? C5 C6 O1 . . . 119.32(10) y C5 C6 C1 . . . 123.71(11) y O1 C6 C1 . . . 116.98(10) y O3 C7 H7A . . . 109.5 ? O3 C7 H7B . . . 109.5 ? H7A C7 H7B . . . 109.5 ? O3 C7 H7C . . . 109.5 ? H7A C7 H7C . . . 109.5 ? H7B C7 H7C . . . 109.5 ? C12 C11 C13 . . . 112.10(11) y C12 C11 P1 . . . 109.97(9) y C13 C11 P1 . . . 111.41(9) y C12 C11 H11 . . . 107.7 ? C13 C11 H11 . . . 107.7 ? P1 C11 H11 . . . 107.7 ? 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 ? C11 C13 H13A . . . 109.5 ? C11 C13 H13B . . . 109.5 ? H13A C13 H13B . . . 109.5 ? C11 C13 H13C . . . 109.5 ? H13A C13 H13C . . . 109.5 ? H13B C13 H13C . . . 109.5 ? C16 C14 C15 . . . 111.83(11) y C16 C14 P1 . . . 109.76(9) y C15 C14 P1 . . . 113.20(9) y C16 C14 H14 . . . 107.2 ? C15 C14 H14 . . . 107.2 ? P1 C14 H14 . . . 107.2 ? 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 ? C23 C21 C22 . . . 111.76(10) y C23 C21 P2 . . . 113.69(9) y C22 C21 P2 . . . 109.36(8) y C23 C21 H21 . . . 107.2 ? C22 C21 H21 . . . 107.2 ? P2 C21 H21 . . . 107.2 ? 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 ? C21 C23 H23A . . . 109.5 ? C21 C23 H23B . . . 109.5 ? H23A C23 H23B . . . 109.5 ? C21 C23 H23C . . . 109.5 ? H23A C23 H23C . . . 109.5 ? H23B C23 H23C . . . 109.5 ? C26 C24 C25 . . . 111.05(10) y C26 C24 P2 . . . 112.77(8) y C25 C24 P2 . . . 108.83(8) y C26 C24 H24 . . . 108.0 ? C25 C24 H24 . . . 108.0 ? P2 C24 H24 . . . 108.0 ? C24 C25 H25A . . . 109.5 ? C24 C25 H25B . . . 109.5 ? H25A C25 H25B . . . 109.5 ? C24 C25 H25C . . . 109.5 ? H25A C25 H25C . . . 109.5 ? H25B C25 H25C . . . 109.5 ? C24 C26 H26A . . . 109.5 ? C24 C26 H26B . . . 109.5 ? H26A C26 H26B . . . 109.5 ? C24 C26 H26C . . . 109.5 ? H26A C26 H26C . . . 109.5 ? H26B C26 H26C . . . 109.5 ? C1 NI1 P2 . . . 82.41(4) y C1 NI1 P1 . . . 82.11(4) y P2 NI1 P1 . . . 164.476(15 y C1 NI1 CL1 . . . 177.49(4) y P2 NI1 CL1 . . . 95.185(13) y P1 NI1 CL1 . . . 100.273(13 y C6 O1 P1 . . . 111.58(7) y C2 O2 P2 . . . 111.05(7) y C4 O3 C7 . . . 116.08(10) y O1 P1 C14 . . . 102.88(5) y O1 P1 C11 . . . 100.90(5) y C14 P1 C11 . . . 106.38(6) y O1 P1 NI1 . . . 106.12(3) y C14 P1 NI1 . . . 116.39(4) y C11 P1 NI1 . . . 121.44(4) y O2 P2 C21 . . . 103.61(5) y O2 P2 C24 . . . 100.51(5) y C21 P2 C24 . . . 107.24(5) y O2 P2 NI1 . . . 106.30(3) y C21 P2 NI1 . . . 117.28(4) y C24 P2 NI1 . . . 119.34(4) y loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C6 C1 C2 O2 . . . . 178.13(10) y NI1 C1 C2 O2 . . . . -2.49(15) y C6 C1 C2 C3 . . . . -0.82(17) y NI1 C1 C2 C3 . . . . 178.55(9) y O2 C2 C3 C4 . . . . -177.07(10) y C1 C2 C3 C4 . . . . 1.89(17) y C2 C3 C4 O3 . . . . 178.81(11) y C2 C3 C4 C5 . . . . -1.40(17) y O3 C4 C5 C6 . . . . 179.74(10) y C3 C4 C5 C6 . . . . -0.08(18) y C4 C5 C6 O1 . . . . -178.28(11) y C4 C5 C6 C1 . . . . 1.23(18) y C2 C1 C6 C5 . . . . -0.80(18) y NI1 C1 C6 C5 . . . . 179.84(9) y C2 C1 C6 O1 . . . . 178.72(10) y NI1 C1 C6 O1 . . . . -0.65(15) y C2 C1 NI1 P2 . . . . 2.94(9) y C6 C1 NI1 P2 . . . . -177.74(10) y C2 C1 NI1 P1 . . . . -175.84(10) y C6 C1 NI1 P1 . . . . 3.49(9) y C2 C1 NI1 CL1 . . . . -13.8(9) y C6 C1 NI1 CL1 . . . . 165.5(7) y C5 C6 O1 P1 . . . . 175.77(9) y C1 C6 O1 P1 . . . . -3.78(13) y C1 C2 O2 P2 . . . . -0.05(13) y C3 C2 O2 P2 . . . . 178.97(8) y C3 C4 O3 C7 . . . . 2.69(18) y C5 C4 O3 C7 . . . . -177.12(12) y C6 O1 P1 C14 . . . . -117.00(8) y C6 O1 P1 C11 . . . . 133.21(8) y C6 O1 P1 NI1 . . . . 5.73(8) y C16 C14 P1 O1 . . . . 71.45(9) y C15 C14 P1 O1 . . . . -54.27(10) y C16 C14 P1 C11 . . . . 177.08(9) y C15 C14 P1 C11 . . . . 51.36(11) y C16 C14 P1 NI1 . . . . -44.10(10) y C15 C14 P1 NI1 . . . . -169.82(8) y C12 C11 P1 O1 . . . . -68.42(10) y C13 C11 P1 O1 . . . . 166.66(9) y C12 C11 P1 C14 . . . . -175.47(9) y C13 C11 P1 C14 . . . . 59.61(10) y C12 C11 P1 NI1 . . . . 48.26(11) y C13 C11 P1 NI1 . . . . -76.66(10) y C1 NI1 P1 O1 . . . . -4.69(5) y P2 NI1 P1 O1 . . . . -9.23(7) y CL1 NI1 P1 O1 . . . . 176.10(4) y C1 NI1 P1 C14 . . . . 109.03(6) y P2 NI1 P1 C14 . . . . 104.50(7) y CL1 NI1 P1 C14 . . . . -70.18(5) y C1 NI1 P1 C11 . . . . -118.73(6) y P2 NI1 P1 C11 . . . . -123.26(7) y CL1 NI1 P1 C11 . . . . 62.06(5) y C2 O2 P2 C21 . . . . -122.21(8) y C2 O2 P2 C24 . . . . 126.99(8) y C2 O2 P2 NI1 . . . . 2.00(8) y C23 C21 P2 O2 . . . . -49.93(9) y C22 C21 P2 O2 . . . . 75.75(9) y C23 C21 P2 C24 . . . . 55.83(10) y C22 C21 P2 C24 . . . . -178.48(8) y C23 C21 P2 NI1 . . . . -166.66(7) y C22 C21 P2 NI1 . . . . -40.98(9) y C26 C24 P2 O2 . . . . 155.39(8) y C25 C24 P2 O2 . . . . -80.91(9) y C26 C24 P2 C21 . . . . 47.45(10) y C25 C24 P2 C21 . . . . 171.15(8) y C26 C24 P2 NI1 . . . . -89.02(9) y C25 C24 P2 NI1 . . . . 34.68(10) y C1 NI1 P2 O2 . . . . -2.49(5) y P1 NI1 P2 O2 . . . . 2.05(7) y CL1 NI1 P2 O2 . . . . 176.79(3) y C1 NI1 P2 C21 . . . . 112.77(5) y P1 NI1 P2 C21 . . . . 117.30(6) y CL1 NI1 P2 C21 . . . . -67.96(4) y C1 NI1 P2 C24 . . . . -114.97(6) y P1 NI1 P2 C24 . . . . -110.44(6) y CL1 NI1 P2 C24 . . . . 64.30(5) y _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 71.18 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.420 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.054 #=== END OF THE CIF FILE _database_code_depnum_ccdc_archive 'CCDC 928921' ####################################################################### # # 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_bors58 #TrackingRef 'web_deposit_cif_file_0_Boris_1363102032.BORS58.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H33 Cl Ni O4 P2' _chemical_formula_sum 'C20 H33 Cl Ni O4 P2' _chemical_formula_weight 493.56 _chemical_compound_source 'Synthesized by the authors. See text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 15.9080(12) _cell_length_b 13.0746(10) _cell_length_c 11.1340(8) _cell_angle_alpha 90 _cell_angle_beta 91.464(3) _cell_angle_gamma 90 _cell_volume 2315.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 61373 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 69.38 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 3.766 _exptl_absorpt_correction_Type multi-scan _exptl_absorpt_correction_T_min 0.4582 _exptl_absorpt_correction_T_max 0.6364 _exptl_absorpt_process_details 'Sadabs (Sheldrick, 2008)' _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker microstar diffractometer equiped with a Platinum 135 CCD Detector, a Helios optics and a Kappa goniometer. The crystal-to-detector distance was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 10.0 degree scan in 33 frames over three different parts of the reciprocal space (99 frames total). ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Helios optics' _diffrn_measurement_device_type 'Bruker Microstar' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.3 _diffrn_reflns_number 71820 _diffrn_reflns_av_R_equivalents 0.051 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 69.76 _reflns_number_total 4345 _reflns_number_gt 4333 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker AXS, 2009)' _computing_cell_refinement 'SAINT V7.68A(Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A(Bruker AXS, 2009)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Bruker AXS, 2003)' _computing_publication_material 'UdMX (Maris, 2004)' _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^)+(0.0579P)^2^+1.0935P] 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 4345 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0305 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0845 _refine_ls_wR_factor_gt 0.0844 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 C1 C 0.71833(8) 0.10725(11) 0.20566(12) 0.0181(3) Uani 1 1 d . . . C2 C 0.66851(8) 0.11820(11) 0.10089(12) 0.0184(3) Uani 1 1 d . . . C3 C 0.61316(8) 0.19865(11) 0.08236(12) 0.0190(3) Uani 1 1 d . . . H3 H 0.5785 0.2020 0.0117 0.023 Uiso 1 1 calc R . . C4 C 0.60950(8) 0.27475(11) 0.17013(12) 0.0183(3) Uani 1 1 d . . . C5 C 0.65962(8) 0.26968(11) 0.27498(12) 0.0196(3) Uani 1 1 d . . . H5 H 0.6584 0.3226 0.3334 0.023 Uiso 1 1 calc R . . C6 C 0.71113(8) 0.18511(11) 0.29098(12) 0.0186(3) Uani 1 1 d . . . C7 C 0.54867(9) 0.35972(11) 0.14789(12) 0.0197(3) Uani 1 1 d . . . C8 C 0.49567(10) 0.51719(12) 0.21363(15) 0.0294(3) Uani 1 1 d . . . H8A H 0.5089 0.5526 0.1389 0.044 Uiso 1 1 calc R . . H8B H 0.5010 0.5650 0.2812 0.044 Uiso 1 1 calc R . . H8C H 0.4380 0.4910 0.2082 0.044 Uiso 1 1 calc R . . C11 C 0.91950(9) 0.11163(12) 0.43164(13) 0.0233(3) Uani 1 1 d . . . H11 H 0.9564 0.0498 0.4375 0.028 Uiso 1 1 calc R . . C12 C 0.94756(10) 0.17397(13) 0.32323(15) 0.0308(3) Uani 1 1 d . . . H12A H 0.9102 0.2330 0.3118 0.046 Uiso 1 1 calc R . . H12B H 0.9450 0.1310 0.2511 0.046 Uiso 1 1 calc R . . H12C H 1.0054 0.1978 0.3374 0.046 Uiso 1 1 calc R . . C13 C 0.93041(11) 0.17094(13) 0.54992(15) 0.0322(4) Uani 1 1 d . . . H13A H 0.9882 0.1966 0.5576 0.048 Uiso 1 1 calc R . . H13B H 0.9189 0.1255 0.6175 0.048 Uiso 1 1 calc R . . H13C H 0.8911 0.2287 0.5501 0.048 Uiso 1 1 calc R . . C14 C 0.77627(9) 0.00796(11) 0.54004(13) 0.0224(3) Uani 1 1 d . . . H14 H 0.7746 0.0614 0.6042 0.027 Uiso 1 1 calc R . . C15 C 0.68725(10) -0.03308(15) 0.51811(16) 0.0330(4) Uani 1 1 d . . . H15A H 0.6882 -0.0872 0.4572 0.050 Uiso 1 1 calc R . . H15B H 0.6505 0.0226 0.4899 0.050 Uiso 1 1 calc R . . H15C H 0.6660 -0.0610 0.5932 0.050 Uiso 1 1 calc R . . C16 C 0.83620(10) -0.07724(13) 0.58185(14) 0.0281(3) Uani 1 1 d . . . H16A H 0.8123 -0.1131 0.6503 0.042 Uiso 1 1 calc R . . H16B H 0.8906 -0.0475 0.6060 0.042 Uiso 1 1 calc R . . H16C H 0.8441 -0.1257 0.5159 0.042 Uiso 1 1 calc R . . C21 C 0.82141(10) -0.03181(12) -0.06998(13) 0.0255(3) Uani 1 1 d . . . H21 H 0.7897 -0.0360 -0.1485 0.031 Uiso 1 1 calc R . . C22 C 0.86441(12) 0.07272(14) -0.06243(17) 0.0373(4) Uani 1 1 d . . . H22A H 0.8971 0.0777 0.0131 0.056 Uiso 1 1 calc R . . H22B H 0.8217 0.1267 -0.0654 0.056 Uiso 1 1 calc R . . H22C H 0.9020 0.0807 -0.1302 0.056 Uiso 1 1 calc R . . C23 C 0.88554(11) -0.11872(14) -0.06503(16) 0.0342(4) Uani 1 1 d . . . H23A H 0.9256 -0.1100 -0.1296 0.051 Uiso 1 1 calc R . . H23B H 0.8564 -0.1843 -0.0751 0.051 Uiso 1 1 calc R . . H23C H 0.9158 -0.1177 0.0128 0.051 Uiso 1 1 calc R . . C24 C 0.68959(9) -0.16334(11) 0.02329(13) 0.0238(3) Uani 1 1 d . . . H24 H 0.7284 -0.2206 0.0462 0.029 Uiso 1 1 calc R . . C25 C 0.66298(11) -0.17885(14) -0.10849(15) 0.0345(4) Uani 1 1 d . . . H25A H 0.6233 -0.2361 -0.1149 0.052 Uiso 1 1 calc R . . H25B H 0.7127 -0.1940 -0.1556 0.052 Uiso 1 1 calc R . . H25C H 0.6359 -0.1165 -0.1393 0.052 Uiso 1 1 calc R . . C26 C 0.61452(11) -0.16866(14) 0.10585(16) 0.0340(4) Uani 1 1 d . . . H26A H 0.5744 -0.1144 0.0842 0.051 Uiso 1 1 calc R . . H26B H 0.6339 -0.1595 0.1894 0.051 Uiso 1 1 calc R . . H26C H 0.5870 -0.2354 0.0969 0.051 Uiso 1 1 calc R . . Cl1 Cl 0.86754(3) -0.14117(3) 0.26030(4) 0.03739(12) Uani 1 1 d . . . Ni1 Ni 0.788110(14) -0.006699(18) 0.23101(2) 0.01816(10) Uani 1 1 d . . . O1 O 0.75806(6) 0.17518(8) 0.39759(9) 0.0220(2) Uani 1 1 d . . . O2 O 0.67522(6) 0.04375(8) 0.01245(9) 0.0218(2) Uani 1 1 d . . . O3 O 0.49966(7) 0.36294(8) 0.06343(10) 0.0276(2) Uani 1 1 d . . . O4 O 0.55349(6) 0.43282(8) 0.23234(9) 0.0247(2) Uani 1 1 d . . . P1 P 0.81245(2) 0.06741(3) 0.40189(3) 0.01790(10) Uani 1 1 d . . . P2 P 0.74631(2) -0.04383(3) 0.05033(3) 0.01856(10) Uani 1 1 d . . . 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 C1 0.0163(6) 0.0192(7) 0.0188(6) 0.0005(5) 0.0017(5) 0.0010(5) C2 0.0192(6) 0.0188(7) 0.0172(6) -0.0018(5) 0.0023(5) -0.0002(5) C3 0.0183(6) 0.0212(7) 0.0174(6) 0.0021(5) -0.0008(5) 0.0005(5) C4 0.0163(6) 0.0188(7) 0.0199(6) 0.0020(5) 0.0026(5) 0.0008(5) C5 0.0194(6) 0.0206(7) 0.0187(6) -0.0018(5) 0.0021(5) 0.0016(5) C6 0.0166(6) 0.0221(7) 0.0169(6) 0.0006(5) -0.0008(5) 0.0002(5) C7 0.0181(6) 0.0199(7) 0.0212(7) 0.0017(5) 0.0039(5) 0.0004(5) C8 0.0256(8) 0.0249(8) 0.0377(9) -0.0028(6) -0.0005(7) 0.0101(6) C11 0.0182(6) 0.0244(7) 0.0272(7) 0.0024(6) -0.0026(5) 0.0006(6) C12 0.0268(8) 0.0312(8) 0.0346(8) 0.0049(7) 0.0053(6) -0.0025(6) C13 0.0332(8) 0.0319(8) 0.0309(8) 0.0000(7) -0.0107(6) -0.0066(7) C14 0.0212(7) 0.0257(7) 0.0205(7) -0.0009(5) 0.0016(5) 0.0015(6) C15 0.0214(8) 0.0423(10) 0.0355(9) 0.0016(7) 0.0039(6) -0.0020(7) C16 0.0290(8) 0.0293(8) 0.0261(7) 0.0071(6) 0.0011(6) 0.0036(6) C21 0.0287(8) 0.0257(8) 0.0223(7) -0.0030(6) 0.0042(6) 0.0003(6) C22 0.0380(9) 0.0309(9) 0.0436(10) 0.0020(7) 0.0116(8) -0.0056(7) C23 0.0315(8) 0.0346(9) 0.0369(9) -0.0049(7) 0.0103(7) 0.0059(7) C24 0.0248(7) 0.0205(7) 0.0261(7) -0.0025(6) -0.0013(6) 0.0000(6) C25 0.0367(9) 0.0362(9) 0.0304(8) -0.0097(7) -0.0035(7) -0.0063(7) C26 0.0339(8) 0.0331(9) 0.0352(8) -0.0012(7) 0.0054(7) -0.0075(7) Cl1 0.0485(2) 0.0334(2) 0.0300(2) -0.00165(15) -0.00484(17) 0.02374(18) Ni1 0.01911(15) 0.01812(15) 0.01716(15) -0.00155(9) -0.00148(10) 0.00425(9) O1 0.0234(5) 0.0233(5) 0.0189(5) -0.0042(4) -0.0053(4) 0.0067(4) O2 0.0262(5) 0.0210(5) 0.0181(5) -0.0038(4) -0.0034(4) 0.0054(4) O3 0.0263(5) 0.0260(5) 0.0300(6) -0.0003(4) -0.0077(4) 0.0055(4) O4 0.0237(5) 0.0237(5) 0.0265(5) -0.0041(4) -0.0019(4) 0.0091(4) P1 0.01698(18) 0.01965(19) 0.01696(18) -0.00084(13) -0.00166(13) 0.00293(13) P2 0.02052(19) 0.01784(19) 0.01727(18) -0.00227(13) -0.00034(13) 0.00224(13) _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_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 C6 . . 1.399(2) y C1 C2 . . 1.4007(19) y C1 Ni1 . . 1.8750(14) y C2 C3 . . 1.384(2) y C2 O2 . . 1.3907(16) y C3 C4 . . 1.397(2) y C3 H3 . . 0.9500 ? C4 C5 . . 1.3983(19) y C4 C7 . . 1.4898(19) y C5 C6 . . 1.385(2) y C5 H5 . . 0.9500 ? C6 O1 . . 1.3920(16) y C7 O3 . . 1.2069(18) y C7 O4 . . 1.3416(18) y C8 O4 . . 1.4479(18) y C8 H8a . . 0.9800 ? C8 H8b . . 0.9800 ? C8 H8c . . 0.9800 ? C11 C12 . . 1.532(2) y C11 C13 . . 1.534(2) y C11 P1 . . 1.8207(14) y C11 H11 . . 1.0000 ? C12 H12a . . 0.9800 ? C12 H12b . . 0.9800 ? C12 H12c . . 0.9800 ? C13 H13a . . 0.9800 ? C13 H13b . . 0.9800 ? C13 H13c . . 0.9800 ? C14 C15 . . 1.528(2) y C14 C16 . . 1.531(2) y C14 P1 . . 1.8293(15) y C14 H14 . . 1.0000 ? C15 H15a . . 0.9800 ? C15 H15b . . 0.9800 ? C15 H15c . . 0.9800 ? C16 H16a . . 0.9800 ? C16 H16b . . 0.9800 ? C16 H16c . . 0.9800 ? C21 C23 . . 1.527(2) y C21 C22 . . 1.530(2) y C21 P2 . . 1.8243(15) y C21 H21 . . 1.0000 ? C22 H22a . . 0.9800 ? C22 H22b . . 0.9800 ? C22 H22c . . 0.9800 ? C23 H23a . . 0.9800 ? C23 H23b . . 0.9800 ? C23 H23c . . 0.9800 ? C24 C26 . . 1.527(2) y C24 C25 . . 1.530(2) y C24 P2 . . 1.8255(15) y C24 H24 . . 1.0000 ? C25 H25a . . 0.9800 ? C25 H25b . . 0.9800 ? C25 H25c . . 0.9800 ? C26 H26a . . 0.9800 ? C26 H26b . . 0.9800 ? C26 H26c . . 0.9800 ? Cl1 Ni1 . . 2.1848(4) y Ni1 P2 . . 2.1578(4) y Ni1 P1 . . 2.1613(4) y O1 P1 . . 1.6536(10) y O2 P2 . . 1.6564(10) y loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C6 C1 C2 . . . 115.90(12) y C6 C1 NI1 . . . 122.30(10) y C2 C1 NI1 . . . 121.79(10) y C3 C2 O2 . . . 119.11(12) y C3 C2 C1 . . . 123.11(13) y O2 C2 C1 . . . 117.78(12) y C2 C3 C4 . . . 118.35(12) y C2 C3 H3 . . . 120.8 ? C4 C3 H3 . . . 120.8 ? C3 C4 C5 . . . 121.14(12) y C3 C4 C7 . . . 116.96(12) y C5 C4 C7 . . . 121.88(12) y C6 C5 C4 . . . 117.91(12) y C6 C5 H5 . . . 121.0 ? C4 C5 H5 . . . 121.0 ? C5 C6 O1 . . . 119.13(12) y C5 C6 C1 . . . 123.50(12) y O1 C6 C1 . . . 117.37(12) y O3 C7 O4 . . . 123.06(13) y O3 C7 C4 . . . 124.02(13) y O4 C7 C4 . . . 112.92(12) y O4 C8 H8A . . . 109.5 ? O4 C8 H8B . . . 109.5 ? H8A C8 H8B . . . 109.5 ? O4 C8 H8C . . . 109.5 ? H8A C8 H8C . . . 109.5 ? H8B C8 H8C . . . 109.5 ? C12 C11 C13 . . . 112.23(13) y C12 C11 P1 . . . 108.39(10) y C13 C11 P1 . . . 113.67(11) y C12 C11 H11 . . . 107.4 ? C13 C11 H11 . . . 107.4 ? P1 C11 H11 . . . 107.4 ? 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 ? C11 C13 H13A . . . 109.5 ? C11 C13 H13B . . . 109.5 ? H13A C13 H13B . . . 109.5 ? C11 C13 H13C . . . 109.5 ? H13A C13 H13C . . . 109.5 ? H13B C13 H13C . . . 109.5 ? C15 C14 C16 . . . 111.13(13) y C15 C14 P1 . . . 108.97(11) y C16 C14 P1 . . . 110.97(10) y C15 C14 H14 . . . 108.6 ? C16 C14 H14 . . . 108.6 ? P1 C14 H14 . . . 108.6 ? 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 ? C23 C21 C22 . . . 111.44(14) y C23 C21 P2 . . . 111.03(11) y C22 C21 P2 . . . 109.69(11) y C23 C21 H21 . . . 108.2 ? C22 C21 H21 . . . 108.2 ? P2 C21 H21 . . . 108.2 ? 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 ? C21 C23 H23A . . . 109.5 ? C21 C23 H23B . . . 109.5 ? H23A C23 H23B . . . 109.5 ? C21 C23 H23C . . . 109.5 ? H23A C23 H23C . . . 109.5 ? H23B C23 H23C . . . 109.5 ? C26 C24 C25 . . . 111.70(13) y C26 C24 P2 . . . 109.30(11) y C25 C24 P2 . . . 113.27(11) y C26 C24 H24 . . . 107.4 ? C25 C24 H24 . . . 107.4 ? P2 C24 H24 . . . 107.4 ? C24 C25 H25A . . . 109.5 ? C24 C25 H25B . . . 109.5 ? H25A C25 H25B . . . 109.5 ? C24 C25 H25C . . . 109.5 ? H25A C25 H25C . . . 109.5 ? H25B C25 H25C . . . 109.5 ? C24 C26 H26A . . . 109.5 ? C24 C26 H26B . . . 109.5 ? H26A C26 H26B . . . 109.5 ? C24 C26 H26C . . . 109.5 ? H26A C26 H26C . . . 109.5 ? H26B C26 H26C . . . 109.5 ? C1 NI1 P2 . . . 82.60(4) y C1 NI1 P1 . . . 82.44(4) y P2 NI1 P1 . . . 164.919(18 y C1 NI1 CL1 . . . 179.02(4) y P2 NI1 CL1 . . . 96.975(17) y P1 NI1 CL1 . . . 98.014(17) y C6 O1 P1 . . . 111.90(8) y C2 O2 P2 . . . 111.58(8) y C7 O4 C8 . . . 114.66(11) y O1 P1 C11 . . . 102.77(6) y O1 P1 C14 . . . 102.17(6) y C11 P1 C14 . . . 107.15(7) y O1 P1 NI1 . . . 105.94(4) y C11 P1 NI1 . . . 116.63(5) y C14 P1 NI1 . . . 119.77(5) y O2 P2 C21 . . . 102.08(6) y O2 P2 C24 . . . 102.61(6) y C21 P2 C24 . . . 106.43(7) y O2 P2 NI1 . . . 105.90(4) y C21 P2 NI1 . . . 118.24(5) y C24 P2 NI1 . . . 119.05(5) y loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C6 C1 C2 C3 . . . . -2.0(2) y NI1 C1 C2 C3 . . . . 176.53(10) y C6 C1 C2 O2 . . . . 178.50(11) y NI1 C1 C2 O2 . . . . -3.02(17) y O2 C2 C3 C4 . . . . -177.65(12) y C1 C2 C3 C4 . . . . 2.8(2) y C2 C3 C4 C5 . . . . -0.7(2) y C2 C3 C4 C7 . . . . -179.43(12) y C3 C4 C5 C6 . . . . -2.0(2) y C7 C4 C5 C6 . . . . 176.61(12) y C4 C5 C6 O1 . . . . -176.34(12) y C4 C5 C6 C1 . . . . 3.0(2) y C2 C1 C6 C5 . . . . -1.0(2) y NI1 C1 C6 C5 . . . . -179.50(10) y C2 C1 C6 O1 . . . . 178.29(11) y NI1 C1 C6 O1 . . . . -0.18(18) y C3 C4 C7 O3 . . . . 4.7(2) y C5 C4 C7 O3 . . . . -173.95(14) y C3 C4 C7 O4 . . . . -175.61(12) y C5 C4 C7 O4 . . . . 5.69(18) y C6 C1 NI1 P2 . . . . -176.74(12) y C2 C1 NI1 P2 . . . . 4.88(10) y C6 C1 NI1 P1 . . . . 1.36(11) y C2 C1 NI1 P1 . . . . -177.02(11) y C6 C1 NI1 CL1 . . . . 119(3) y C2 C1 NI1 CL1 . . . . -60(3) y C5 C6 O1 P1 . . . . 177.74(10) y C1 C6 O1 P1 . . . . -1.61(15) y C3 C2 O2 P2 . . . . 178.53(10) y C1 C2 O2 P2 . . . . -1.91(15) y O3 C7 O4 C8 . . . . -0.7(2) y C4 C7 O4 C8 . . . . 179.65(12) y C6 O1 P1 C11 . . . . 125.21(9) y C6 O1 P1 C14 . . . . -123.80(10) y C6 O1 P1 NI1 . . . . 2.35(9) y C12 C11 P1 O1 . . . . -65.55(11) y C13 C11 P1 O1 . . . . 59.98(12) y C12 C11 P1 C14 . . . . -172.77(10) y C13 C11 P1 C14 . . . . -47.24(13) y C12 C11 P1 NI1 . . . . 49.83(12) y C13 C11 P1 NI1 . . . . 175.36(9) y C15 C14 P1 O1 . . . . 73.92(11) y C16 C14 P1 O1 . . . . -163.40(10) y C15 C14 P1 C11 . . . . -178.43(11) y C16 C14 P1 C11 . . . . -55.75(12) y C15 C14 P1 NI1 . . . . -42.63(12) y C16 C14 P1 NI1 . . . . 80.05(11) y C1 NI1 P1 O1 . . . . -1.90(6) y P2 NI1 P1 O1 . . . . 5.36(8) y CL1 NI1 P1 O1 . . . . 178.98(4) y C1 NI1 P1 C11 . . . . -115.50(7) y P2 NI1 P1 C11 . . . . -108.23(8) y CL1 NI1 P1 C11 . . . . 65.38(6) y C1 NI1 P1 C14 . . . . 112.68(7) y P2 NI1 P1 C14 . . . . 119.94(8) y CL1 NI1 P1 C14 . . . . -66.44(6) y C2 O2 P2 C21 . . . . -119.39(10) y C2 O2 P2 C24 . . . . 130.47(9) y C2 O2 P2 NI1 . . . . 4.94(9) y C23 C21 P2 O2 . . . . -170.27(11) y C22 C21 P2 O2 . . . . 66.12(12) y C23 C21 P2 C24 . . . . -63.06(13) y C22 C21 P2 C24 . . . . 173.33(11) y C23 C21 P2 NI1 . . . . 74.07(12) y C22 C21 P2 NI1 . . . . -49.54(13) y C26 C24 P2 O2 . . . . -62.40(12) y C25 C24 P2 O2 . . . . 62.85(12) y C26 C24 P2 C21 . . . . -169.23(11) y C25 C24 P2 C21 . . . . -43.98(13) y C26 C24 P2 NI1 . . . . 54.06(12) y C25 C24 P2 NI1 . . . . 179.30(9) y C1 NI1 P2 O2 . . . . -5.00(6) y P1 NI1 P2 O2 . . . . -12.26(9) y CL1 NI1 P2 O2 . . . . 174.11(4) y C1 NI1 P2 C21 . . . . 108.58(7) y P1 NI1 P2 C21 . . . . 101.32(9) y CL1 NI1 P2 C21 . . . . -72.31(6) y C1 NI1 P2 C24 . . . . -119.70(7) y P1 NI1 P2 C24 . . . . -126.96(8) y CL1 NI1 P2 C24 . . . . 59.41(6) y _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 69.76 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.531 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.061 #=== END OF THE CIF FILE _database_code_depnum_ccdc_archive 'CCDC 928922' ####################################################################### # # 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_bors24 #TrackingRef 'web_deposit_cif_file_0_Boris_1363101910.Bors24.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H47 Cl Ni O2 P2' _chemical_formula_sum 'C26 H47 Cl Ni O2 P2' _chemical_formula_weight 547.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.4275(4) _cell_length_b 14.0330(5) _cell_length_c 20.5730(7) _cell_angle_alpha 90.00 _cell_angle_beta 101.1800(10) _cell_angle_gamma 90.00 _cell_volume 2953.30(18) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 9840 _cell_measurement_theta_min 3.84 _cell_measurement_theta_max 72.23 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 2.944 _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 200(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 37304 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.84 _diffrn_reflns_theta_max 72.53 _reflns_number_total 5817 _reflns_number_gt 5430 _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 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^)+(0.0821P)^2^+0.6846P] 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 5817 _refine_ls_number_parameters 303 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0464 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1176 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 C1 C 0.91723(16) 0.23896(12) 0.02253(8) 0.0302(3) Uani 1 1 d . . . C2 C 0.91870(15) 0.22547(11) -0.04484(8) 0.0290(3) Uani 1 1 d . . . C3 C 1.00986(15) 0.26702(11) -0.07735(8) 0.0290(3) Uani 1 1 d . . . C4 C 1.10703(16) 0.32151(11) -0.03708(8) 0.0299(3) Uani 1 1 d . . . H4 H 1.1724 0.3493 -0.0574 0.036 Uiso 1 1 calc R . . C5 C 1.11497(15) 0.33801(12) 0.03061(8) 0.0295(3) Uani 1 1 d . . . C6 C 1.01546(16) 0.29704(12) 0.05809(8) 0.0297(3) Uani 1 1 d . . . C11 C 0.99195(18) 0.18241(13) 0.21781(9) 0.0358(4) Uani 1 1 d . . . H11 H 1.0478 0.2275 0.2487 0.043 Uiso 1 1 calc R . . C12 C 1.0811(2) 0.11459(15) 0.18927(11) 0.0486(5) Uani 1 1 d . . . H12A H 1.1373 0.0803 0.2255 0.073 Uiso 1 1 calc R . . H12B H 1.1354 0.1511 0.1643 0.073 Uiso 1 1 calc R . . H12C H 1.0278 0.0688 0.1597 0.073 Uiso 1 1 calc R . . C13 C 0.9051(2) 0.1282(2) 0.25658(12) 0.0612(6) Uani 1 1 d . . . H13A H 0.8416 0.0900 0.2260 0.092 Uiso 1 1 calc R . . H13B H 0.8586 0.1735 0.2799 0.092 Uiso 1 1 calc R . . H13C H 0.9592 0.0861 0.2888 0.092 Uiso 1 1 calc R . . C14 C 0.80498(19) 0.34128(15) 0.18667(9) 0.0417(4) Uani 1 1 d . . . H14 H 0.7376 0.3073 0.2066 0.050 Uiso 1 1 calc R . . C15 C 0.7330(3) 0.4064(2) 0.13190(13) 0.0698(7) Uani 1 1 d . . . H15A H 0.6832 0.4542 0.1512 0.105 Uiso 1 1 calc R . . H15B H 0.6731 0.3682 0.0994 0.105 Uiso 1 1 calc R . . H15C H 0.7966 0.4383 0.1099 0.105 Uiso 1 1 calc R . . C16 C 0.8890(3) 0.39960(17) 0.24124(11) 0.0582(6) Uani 1 1 d . . . H16A H 0.9580 0.4321 0.2234 0.087 Uiso 1 1 calc R . . H16B H 0.9287 0.3573 0.2775 0.087 Uiso 1 1 calc R . . H16C H 0.8344 0.4470 0.2579 0.087 Uiso 1 1 calc R . . C21 C 0.68912(16) 0.00951(12) -0.05545(8) 0.0334(3) Uani 1 1 d . . . H21 H 0.6144 -0.0132 -0.0355 0.040 Uiso 1 1 calc R . . C22 C 0.81118(19) -0.04546(15) -0.02195(10) 0.0469(4) Uani 1 1 d . . . H22A H 0.7961 -0.1140 -0.0288 0.070 Uiso 1 1 calc R . . H22B H 0.8296 -0.0315 0.0256 0.070 Uiso 1 1 calc R . . H22C H 0.8859 -0.0260 -0.0413 0.070 Uiso 1 1 calc R . . C23 C 0.65433(18) -0.01018(14) -0.12993(9) 0.0399(4) Uani 1 1 d . . . H23A H 0.7231 0.0153 -0.1514 0.060 Uiso 1 1 calc R . . H23B H 0.5710 0.0206 -0.1486 0.060 Uiso 1 1 calc R . . H23C H 0.6466 -0.0791 -0.1375 0.060 Uiso 1 1 calc R . . C24 C 0.56605(17) 0.19789(13) -0.07948(9) 0.0355(4) Uani 1 1 d . . . H24 H 0.5577 0.1862 -0.1281 0.043 Uiso 1 1 calc R . . C25 C 0.5845(2) 0.30517(14) -0.06702(12) 0.0492(5) Uani 1 1 d . . . H25A H 0.5114 0.3398 -0.0940 0.074 Uiso 1 1 calc R . . H25B H 0.6666 0.3257 -0.0790 0.074 Uiso 1 1 calc R . . H25C H 0.5871 0.3187 -0.0200 0.074 Uiso 1 1 calc R . . C26 C 0.44206(18) 0.16138(15) -0.05855(12) 0.0474(5) Uani 1 1 d . . . H26A H 0.4514 0.1673 -0.0104 0.071 Uiso 1 1 calc R . . H26B H 0.4284 0.0943 -0.0714 0.071 Uiso 1 1 calc R . . H26C H 0.3670 0.1991 -0.0805 0.071 Uiso 1 1 calc R . . C31 C 1.00564(17) 0.25367(12) -0.15206(8) 0.0330(4) Uani 1 1 d . . . C32 C 1.1097(2) 0.31342(16) -0.17629(10) 0.0481(5) Uani 1 1 d . . . H32A H 1.0979 0.3807 -0.1661 0.072 Uiso 1 1 calc R . . H32B H 1.1010 0.3055 -0.2243 0.072 Uiso 1 1 calc R . . H32C H 1.1967 0.2924 -0.1540 0.072 Uiso 1 1 calc R . . C33 C 1.0298(2) 0.14860(14) -0.16673(10) 0.0465(4) Uani 1 1 d . . . H33A H 1.1160 0.1293 -0.1422 0.070 Uiso 1 1 calc R . . H33B H 1.0266 0.1404 -0.2143 0.070 Uiso 1 1 calc R . . H33C H 0.9622 0.1090 -0.1531 0.070 Uiso 1 1 calc R . . C34 C 0.87247(19) 0.28483(16) -0.19269(9) 0.0435(4) Uani 1 1 d . . . H34A H 0.8032 0.2455 -0.1805 0.065 Uiso 1 1 calc R . . H34B H 0.8725 0.2770 -0.2400 0.065 Uiso 1 1 calc R . . H34C H 0.8569 0.3519 -0.1834 0.065 Uiso 1 1 calc R . . C51 C 1.22641(16) 0.39718(12) 0.07167(8) 0.0340(4) Uani 1 1 d . . . C52 C 1.32460(19) 0.43096(15) 0.03025(10) 0.0464(5) Uani 1 1 d . . . H52A H 1.2805 0.4728 -0.0053 0.070 Uiso 1 1 calc R . . H52B H 1.3608 0.3757 0.0109 0.070 Uiso 1 1 calc R . . H52C H 1.3955 0.4660 0.0586 0.070 Uiso 1 1 calc R . . C53 C 1.3024(2) 0.33626(17) 0.12829(11) 0.0546(6) Uani 1 1 d . . . H53A H 1.3748 0.3736 0.1534 0.082 Uiso 1 1 calc R . . H53B H 1.3371 0.2796 0.1099 0.082 Uiso 1 1 calc R . . H53C H 1.2438 0.3167 0.1578 0.082 Uiso 1 1 calc R . . C54 C 1.1705(2) 0.48568(15) 0.09997(12) 0.0529(5) Uani 1 1 d . . . H54A H 1.2423 0.5246 0.1240 0.079 Uiso 1 1 calc R . . H54B H 1.1137 0.4659 0.1303 0.079 Uiso 1 1 calc R . . H54C H 1.1197 0.5231 0.0637 0.079 Uiso 1 1 calc R . . Cl1 Cl 0.64071(5) 0.11460(5) 0.11077(2) 0.05625(16) Uani 1 1 d . . . Ni1 Ni 0.78933(3) 0.18106(2) 0.063444(13) 0.03086(11) Uani 1 1 d . . . O1 O 1.01200(12) 0.31299(9) 0.12505(6) 0.0353(3) Uani 1 1 d . . . O2 O 0.82081(12) 0.16699(9) -0.08035(6) 0.0347(3) Uani 1 1 d . . . P1 P 0.89592(4) 0.25128(3) 0.14967(2) 0.03076(12) Uani 1 1 d . . . P2 P 0.71226(4) 0.13555(3) -0.036032(19) 0.02927(12) Uani 1 1 d . . . 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 C1 0.0250(7) 0.0352(8) 0.0316(8) -0.0016(6) 0.0085(6) -0.0034(6) C2 0.0223(7) 0.0338(8) 0.0317(8) -0.0024(6) 0.0075(6) -0.0044(6) C3 0.0240(7) 0.0333(8) 0.0314(8) -0.0006(6) 0.0094(6) -0.0009(6) C4 0.0236(7) 0.0345(8) 0.0337(8) 0.0018(6) 0.0108(6) -0.0034(6) C5 0.0236(7) 0.0322(7) 0.0330(8) 0.0004(6) 0.0065(6) -0.0028(6) C6 0.0270(8) 0.0358(8) 0.0273(7) -0.0016(6) 0.0080(6) -0.0026(6) C11 0.0310(8) 0.0438(9) 0.0337(8) -0.0014(7) 0.0094(7) 0.0003(7) C12 0.0474(11) 0.0471(10) 0.0546(12) -0.0001(9) 0.0184(9) 0.0085(9) C13 0.0489(12) 0.0884(17) 0.0505(12) 0.0250(12) 0.0201(10) 0.0038(12) C14 0.0379(9) 0.0498(10) 0.0390(9) -0.0049(8) 0.0116(7) 0.0057(8) C15 0.0752(17) 0.0692(15) 0.0566(13) -0.0095(11) -0.0085(12) 0.0291(13) C16 0.0684(14) 0.0583(13) 0.0434(11) -0.0158(9) -0.0002(10) 0.0162(11) C21 0.0250(7) 0.0366(8) 0.0396(8) -0.0002(7) 0.0091(6) -0.0042(6) C22 0.0387(10) 0.0479(10) 0.0521(11) 0.0023(9) 0.0036(8) 0.0056(8) C23 0.0320(8) 0.0432(9) 0.0447(10) -0.0092(7) 0.0081(7) -0.0037(7) C24 0.0302(8) 0.0381(8) 0.0378(9) 0.0000(7) 0.0057(7) -0.0026(7) C25 0.0465(11) 0.0381(9) 0.0625(13) 0.0042(9) 0.0093(9) 0.0005(8) C26 0.0269(9) 0.0516(11) 0.0638(12) 0.0065(9) 0.0089(8) -0.0001(8) C31 0.0304(8) 0.0402(9) 0.0313(8) -0.0009(6) 0.0132(6) -0.0031(7) C32 0.0459(11) 0.0664(13) 0.0360(9) 0.0019(8) 0.0179(8) -0.0147(9) C33 0.0565(12) 0.0458(10) 0.0414(10) -0.0053(8) 0.0198(9) 0.0039(9) C34 0.0380(9) 0.0598(11) 0.0327(8) 0.0007(8) 0.0067(7) 0.0024(9) C51 0.0284(8) 0.0373(8) 0.0364(8) -0.0015(7) 0.0064(6) -0.0087(7) C52 0.0344(9) 0.0576(12) 0.0486(10) -0.0038(9) 0.0118(8) -0.0181(9) C53 0.0396(11) 0.0645(13) 0.0525(12) 0.0139(10) -0.0089(9) -0.0169(10) C54 0.0513(12) 0.0449(11) 0.0666(13) -0.0174(9) 0.0217(10) -0.0150(9) Cl1 0.0440(3) 0.0841(4) 0.0454(3) -0.0029(2) 0.0206(2) -0.0307(2) Ni1 0.02434(17) 0.04131(19) 0.02903(18) -0.00287(10) 0.01039(12) -0.00837(11) O1 0.0334(6) 0.0453(7) 0.0290(6) -0.0062(5) 0.0110(5) -0.0130(5) O2 0.0293(6) 0.0466(6) 0.0296(6) -0.0071(5) 0.0097(5) -0.0131(5) P1 0.0265(2) 0.0398(2) 0.0280(2) -0.00316(15) 0.01019(16) -0.00448(16) P2 0.0227(2) 0.0364(2) 0.0299(2) -0.00195(15) 0.00801(15) -0.00600(15) _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 C1 C6 1.399(2) . ? C1 C2 1.402(2) . ? C1 Ni1 1.8929(16) . ? C2 C3 1.392(2) . ? C2 O2 1.4000(18) . ? C3 C4 1.404(2) . ? C3 C31 1.540(2) . ? C4 C5 1.398(2) . ? C4 H4 0.9500 . ? C5 C6 1.398(2) . ? C5 C51 1.540(2) . ? C6 O1 1.4030(19) . ? C11 C13 1.522(3) . ? C11 C12 1.525(3) . ? C11 P1 1.8325(18) . ? C11 H11 1.0000 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C16 1.522(3) . ? C14 C15 1.529(3) . ? C14 P1 1.8313(19) . ? C14 H14 1.0000 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C21 C23 1.530(2) . ? C21 C22 1.533(2) . ? C21 P2 1.8190(17) . ? C21 H21 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C26 1.528(3) . ? C24 C25 1.533(3) . ? C24 P2 1.8332(18) . ? C24 H24 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C31 C32 1.529(2) . ? C31 C33 1.536(3) . ? C31 C34 1.539(2) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C51 C52 1.529(2) . ? C51 C53 1.536(3) . ? C51 C54 1.534(3) . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C53 H53C 0.9800 . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? Cl1 Ni1 2.1919(5) . ? Ni1 P1 2.1421(5) . ? Ni1 P2 2.1457(5) . ? O1 P1 1.6459(12) . ? O2 P2 1.6454(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 C6 C1 C2 116.64(14) . . ? C6 C1 Ni1 121.67(12) . . ? C2 C1 Ni1 121.69(12) . . ? C3 C2 O2 119.44(14) . . ? C3 C2 C1 123.91(14) . . ? O2 C2 C1 116.65(13) . . ? C2 C3 C4 115.24(14) . . ? C2 C3 C31 122.58(14) . . ? C4 C3 C31 122.18(14) . . ? C5 C4 C3 125.06(15) . . ? C5 C4 H4 117.5 . . ? C3 C4 H4 117.5 . . ? C4 C5 C6 115.43(14) . . ? C4 C5 C51 121.88(14) . . ? C6 C5 C51 122.69(14) . . ? C5 C6 C1 123.61(15) . . ? C5 C6 O1 119.60(14) . . ? C1 C6 O1 116.78(14) . . ? C13 C11 C12 111.01(18) . . ? C13 C11 P1 111.87(14) . . ? C12 C11 P1 108.54(13) . . ? C13 C11 H11 108.4 . . ? C12 C11 H11 108.4 . . ? P1 C11 H11 108.4 . . ? 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 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C16 C14 C15 110.64(19) . . ? C16 C14 P1 114.01(14) . . ? C15 C14 P1 108.98(15) . . ? C16 C14 H14 107.7 . . ? C15 C14 H14 107.7 . . ? P1 C14 H14 107.7 . . ? 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 . . ? C23 C21 C22 111.99(15) . . ? C23 C21 P2 113.03(12) . . ? C22 C21 P2 109.11(12) . . ? C23 C21 H21 107.5 . . ? C22 C21 H21 107.5 . . ? P2 C21 H21 107.5 . . ? 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 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C26 C24 C25 111.56(16) . . ? C26 C24 P2 111.81(13) . . ? C25 C24 P2 108.77(13) . . ? C26 C24 H24 108.2 . . ? C25 C24 H24 108.2 . . ? P2 C24 H24 108.2 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C32 C31 C33 107.98(16) . . ? C32 C31 C34 106.84(15) . . ? C33 C31 C34 109.34(16) . . ? C32 C31 C3 111.95(14) . . ? C33 C31 C3 109.80(14) . . ? C34 C31 C3 110.83(14) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 C33 H33A 109.5 . . ? C31 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C31 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C31 C34 H34A 109.5 . . ? C31 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C31 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C52 C51 C53 107.01(16) . . ? C52 C51 C54 107.79(16) . . ? C53 C51 C54 109.95(18) . . ? C52 C51 C5 112.15(14) . . ? C53 C51 C5 109.84(14) . . ? C54 C51 C5 110.04(15) . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C51 C53 H53A 109.5 . . ? C51 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C51 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C51 C54 H54A 109.5 . . ? C51 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C51 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? C1 Ni1 P1 82.74(5) . . ? C1 Ni1 P2 82.50(5) . . ? P1 Ni1 P2 164.79(2) . . ? C1 Ni1 Cl1 179.74(6) . . ? P1 Ni1 Cl1 97.24(2) . . ? P2 Ni1 Cl1 97.51(2) . . ? C6 O1 P1 112.26(10) . . ? C2 O2 P2 112.23(10) . . ? O1 P1 C14 103.66(8) . . ? O1 P1 C11 100.81(7) . . ? C14 P1 C11 107.21(8) . . ? O1 P1 Ni1 106.36(4) . . ? C14 P1 Ni1 115.73(6) . . ? C11 P1 Ni1 120.64(6) . . ? O2 P2 C21 102.43(7) . . ? O2 P2 C24 101.43(8) . . ? C21 P2 C24 107.13(8) . . ? O2 P2 Ni1 106.14(4) . . ? C21 P2 Ni1 120.53(6) . . ? C24 P2 Ni1 116.45(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.8(2) . . . . ? Ni1 C1 C2 C3 179.45(13) . . . . ? C6 C1 C2 O2 179.70(14) . . . . ? Ni1 C1 C2 O2 0.0(2) . . . . ? O2 C2 C3 C4 -177.71(14) . . . . ? C1 C2 C3 C4 2.8(2) . . . . ? O2 C2 C3 C31 1.8(2) . . . . ? C1 C2 C3 C31 -177.68(15) . . . . ? C2 C3 C4 C5 -1.9(2) . . . . ? C31 C3 C4 C5 178.65(15) . . . . ? C3 C4 C5 C6 -1.0(2) . . . . ? C3 C4 C5 C51 178.81(15) . . . . ? C4 C5 C6 C1 3.3(2) . . . . ? C51 C5 C6 C1 -176.54(15) . . . . ? C4 C5 C6 O1 -177.34(14) . . . . ? C51 C5 C6 O1 2.8(2) . . . . ? C2 C1 C6 C5 -2.4(3) . . . . ? Ni1 C1 C6 C5 177.26(13) . . . . ? C2 C1 C6 O1 178.17(14) . . . . ? Ni1 C1 C6 O1 -2.1(2) . . . . ? C2 C3 C31 C32 175.22(16) . . . . ? C4 C3 C31 C32 -5.3(2) . . . . ? C2 C3 C31 C33 -64.9(2) . . . . ? C4 C3 C31 C33 114.58(18) . . . . ? C2 C3 C31 C34 56.0(2) . . . . ? C4 C3 C31 C34 -124.52(17) . . . . ? C4 C5 C51 C52 -1.7(2) . . . . ? C6 C5 C51 C52 178.11(16) . . . . ? C4 C5 C51 C53 -120.57(19) . . . . ? C6 C5 C51 C53 59.3(2) . . . . ? C4 C5 C51 C54 118.26(18) . . . . ? C6 C5 C51 C54 -61.9(2) . . . . ? C6 C1 Ni1 P1 -0.75(13) . . . . ? C2 C1 Ni1 P1 178.94(14) . . . . ? C6 C1 Ni1 P2 175.58(14) . . . . ? C2 C1 Ni1 P2 -4.73(13) . . . . ? C6 C1 Ni1 Cl1 83(12) . . . . ? C2 C1 Ni1 Cl1 -97(12) . . . . ? C5 C6 O1 P1 -174.88(12) . . . . ? C1 C6 O1 P1 4.53(19) . . . . ? C3 C2 O2 P2 -172.86(12) . . . . ? C1 C2 O2 P2 6.62(18) . . . . ? C6 O1 P1 C14 -127.12(12) . . . . ? C6 O1 P1 C11 122.00(12) . . . . ? C6 O1 P1 Ni1 -4.64(12) . . . . ? C16 C14 P1 O1 -55.36(18) . . . . ? C15 C14 P1 O1 68.79(18) . . . . ? C16 C14 P1 C11 50.74(18) . . . . ? C15 C14 P1 C11 174.89(17) . . . . ? C16 C14 P1 Ni1 -171.39(14) . . . . ? C15 C14 P1 Ni1 -47.24(19) . . . . ? C13 C11 P1 O1 171.88(15) . . . . ? C12 C11 P1 O1 -65.29(14) . . . . ? C13 C11 P1 C14 63.77(18) . . . . ? C12 C11 P1 C14 -173.40(14) . . . . ? C13 C11 P1 Ni1 -71.61(16) . . . . ? C12 C11 P1 Ni1 51.22(15) . . . . ? C1 Ni1 P1 O1 2.82(7) . . . . ? P2 Ni1 P1 O1 -11.18(10) . . . . ? Cl1 Ni1 P1 O1 -176.93(5) . . . . ? C1 Ni1 P1 C14 117.31(9) . . . . ? P2 Ni1 P1 C14 103.31(11) . . . . ? Cl1 Ni1 P1 C14 -62.43(8) . . . . ? C1 Ni1 P1 C11 -110.83(8) . . . . ? P2 Ni1 P1 C11 -124.83(10) . . . . ? Cl1 Ni1 P1 C11 69.42(7) . . . . ? C2 O2 P2 C21 -136.47(11) . . . . ? C2 O2 P2 C24 112.90(12) . . . . ? C2 O2 P2 Ni1 -9.21(12) . . . . ? C23 C21 P2 O2 -53.41(13) . . . . ? C22 C21 P2 O2 71.89(14) . . . . ? C23 C21 P2 C24 52.88(14) . . . . ? C22 C21 P2 C24 178.18(13) . . . . ? C23 C21 P2 Ni1 -170.83(9) . . . . ? C22 C21 P2 Ni1 -45.53(14) . . . . ? C26 C24 P2 O2 165.98(13) . . . . ? C25 C24 P2 O2 -70.37(14) . . . . ? C26 C24 P2 C21 58.99(15) . . . . ? C25 C24 P2 C21 -177.36(13) . . . . ? C26 C24 P2 Ni1 -79.35(14) . . . . ? C25 C24 P2 Ni1 44.30(15) . . . . ? C1 Ni1 P2 O2 7.15(7) . . . . ? P1 Ni1 P2 O2 21.15(10) . . . . ? Cl1 Ni1 P2 O2 -173.11(5) . . . . ? C1 Ni1 P2 C21 122.67(8) . . . . ? P1 Ni1 P2 C21 136.67(9) . . . . ? Cl1 Ni1 P2 C21 -57.59(7) . . . . ? C1 Ni1 P2 C24 -104.85(8) . . . . ? P1 Ni1 P2 C24 -90.84(10) . . . . ? Cl1 Ni1 P2 C24 74.89(7) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 72.53 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.368 _refine_diff_density_min -0.827 _refine_diff_density_rms 0.137 _database_code_depnum_ccdc_archive 'CCDC 928920'