# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #============================================================================== # 1. SUBMISSION DETAILS #============================================================================== _publ_contact_author_name 'Dr Davit Zargarian' _publ_contact_author_address ; Universit\'e de Montr\'eal D\'epartement de Chimie C.P. 6128, Succ. Centre-ville Montr\'eal, Qu\'ebec Canada, H3C 3J7 ; _publ_contact_author_phone '+1 514 343 2247' _publ_contact_author_fax '+1 514 343 7586' _publ_contact_author_email davitz@chimie.umontreal.ca _publ_section_title ; Structure of valer4 ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address D.Zargarian ; D\'epartement de Chimie Universit\'e de Montr\'eal C.P. 6128, Succ. Centre-ville, Montr\'eal, Qu\'ebec Canada H3C 3J7 ; V.Pandarus ; D\'epartement de Chimie Universit\'e de Montr\'eal C.P. 6128, Succ. Centre-ville, Montr\'eal, Qu\'ebec Canada H3C 3J7 ; #============================================================================== # 4. TEXT #============================================================================== _publ_section_abstract ; Here should be written a short abstract ; _publ_section_comment ; Here should be written the text of the article ; _publ_section_exptl_prep ; Small details about the preparation of the compound. ; _publ_section_exptl_refinement ; All non-H atoms were refined by full-matrix least-squares with anisotropic displacement parameters. The H atoms were generated geometrically (C-H 0.93 to 0.98, N-H 0.86 and O-H 0.82\%A) and were included in the refinement in the riding model approximation; their temperature factors were set to 1.5 times those of the equivalent isotropic temperature factors of the parent site (methyl) and 1.2 times for others. A final verification of possible voids was performed using the VOID routine of the PLATON program (Spek, 2000). ; _publ_section_references ; Bruker (1997). SHELXTL (1997). Release 5.10; The Complete Software Package for Single Crystal Structure Determination. Bruker AXS Inc., Madison, USA. Bruker (1999a). SAINT Release 6.06. Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, USA. Bruker (1999b). SMART Release 5.059; Bruker Molecular Analysis Research Tool, Bruker AXS Inc., Madison, USA. Sheldrick, G. M. (1986). SHELXS86. Program for Crystal Structure solution. University of G\"ottingen, Germany. Sheldrick, G. M. (1996). SADABS, Bruker Area Detector Absorption Corrections. Bruker AXS Inc., Madison, USA. Sheldrick, G. M. (1997a). SHELXS97. Program for Crystal Structure solution. University of G\"ottingen, Germany. Sheldrick, G. M. (1997b). SHELXL97. Program for crystal structure refinement. University of G\"ottingen, Germany. Spek, A. L. (2000). PLATON, 2000 version; Molecular Geometry Program, University of Utrecht, Utrecht, Holland. ; _publ_section_figure_captions ; Fig 1 Ortep view of the title compound. Thermal ellipsoids are shown at 30% probability levels. ; _publ_section_table_legends ; Table 1. Selected geometric parameters (\%A, \%) for the title compound. ; _publ_section_acknowledgements ; We are grateful to the Natural Sciences and Engineering Research Council of Canada and the Minist\`ere de l'Education du Qu\'ebec for financial support. ; # ======================================================== # STRUCTURAL DATA # ======================================================== data_valer4 _database_code_depnum_ccdc_archive 'CCDC 620341' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H33 Br Ni O2 P2' _chemical_formula_sum 'C15 H33 Br Ni O2 P2' _chemical_formula_weight 445.97 _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' Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 _symmetry_space_group_name_hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.7081(1) _cell_length_b 13.9372(2) _cell_length_c 17.1214(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2077.97(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 19980 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 72.86 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 5.062 _exptl_absorpt_correction_Type multi-scan _exptl_absorpt_correction_T_min 0.610 _exptl_absorpt_correction_T_max 0.780 _exptl_absorpt_process_details 'Sadabs (Sheldrick,1996)' _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 Platform diffractometer, equipped with a Bruker SMART 2K Charged-Coupled Device (CCD) Area Detector using the program SMART and normal focus sealed tube source graphite monochromated Cu-K\a radiation. The crystal-to-detector distance was 4.908 cm, and the data collection was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 9.0 degree scan in 30 frames over four different parts of the reciprocal space (120 frames total). One complete sphere of data was collected, to better than 0.8\%A resolution. Upon completion of the data collection, the first 101 frames were recollected in order to improve the decay correction analysis. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart 2000' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.5 _diffrn_standards_number 192 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% -0.25 _diffrn_reflns_number 25133 _diffrn_reflns_av_R_equivalents 0.044 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.09 _diffrn_reflns_theta_max 72.85 _reflns_number_total 4116 _reflns_number_gt 3847 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1999)' _computing_cell_refinement 'SMART (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'UdMX (local program)' _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^)+(0.0444P)^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_abs_structure_details 'Flack H D (1983), 1750 Friedel Pairs' _chemical_absolute_configuration rmad _refine_ls_abs_structure_Flack 0.02(2) _refine_ls_number_reflns 4116 _refine_ls_number_parameters 198 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0709 _refine_ls_wR_factor_gt 0.0698 _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_restrained_S_all 0.986 _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 Ni1 Ni 0.33993(6) 0.12888(3) 0.19402(3) 0.01674(11) Uani 1 1 d . . . Br1 Br 0.41283(5) 0.28783(2) 0.168409(18) 0.03028(10) Uani 1 1 d . . . P1 P 0.41059(9) 0.06901(5) 0.08352(4) 0.01604(13) Uani 1 1 d . . . P2 P 0.25504(9) 0.15422(5) 0.31029(4) 0.01833(15) Uani 1 1 d . . . O1 O 0.3906(3) -0.04734(14) 0.08990(11) 0.0239(5) Uani 1 1 d . . . O2 O 0.2025(3) 0.05050(15) 0.34527(12) 0.0283(5) Uani 1 1 d . . . C1 C 0.3465(4) -0.07729(19) 0.16684(18) 0.0264(6) Uani 1 1 d . . . H1A H 0.4397 -0.0974 0.1957 0.032 Uiso 1 1 calc R . . H1B H 0.2787 -0.1340 0.1623 0.032 Uiso 1 1 calc R . . C2 C 0.2653(5) -0.0020(2) 0.2134(2) 0.0387(9) Uani 1 1 d . . . H2 H 0.1584 -0.0020 0.1920 0.046 Uiso 1 1 calc R . . C3 C 0.2462(4) -0.0286(2) 0.29647(18) 0.0285(7) Uani 1 1 d . . . H3A H 0.1669 -0.0793 0.3005 0.034 Uiso 1 1 calc R . . H3B H 0.3440 -0.0557 0.3160 0.034 Uiso 1 1 calc R . . C4 C 0.6105(3) 0.0843(2) 0.05328(19) 0.0264(7) Uani 1 1 d . . . H4 H 0.6223 0.1520 0.0350 0.032 Uiso 1 1 calc R . . C5 C 0.2940(3) 0.0957(2) -0.00274(16) 0.0201(6) Uani 1 1 d . . . H5 H 0.3128 0.0439 -0.0421 0.024 Uiso 1 1 calc R . . C6 C 0.0779(4) 0.2226(2) 0.32566(17) 0.0267(6) Uani 1 1 d . . . H6 H 0.0373 0.2059 0.3786 0.032 Uiso 1 1 calc R . . C7 C 0.3945(4) 0.1999(2) 0.38199(16) 0.0267(7) Uani 1 1 d . . . H7 H 0.4204 0.2673 0.3669 0.032 Uiso 1 1 calc R . . C8 C 0.7152(4) 0.0714(3) 0.1235(2) 0.0384(9) Uani 1 1 d . . . H8A H 0.7119 0.0044 0.1408 0.058 Uiso 1 1 calc R . . H8B H 0.6806 0.1132 0.1660 0.058 Uiso 1 1 calc R . . H8C H 0.8206 0.0883 0.1090 0.058 Uiso 1 1 calc R . . C9 C 0.6550(4) 0.0193(3) -0.0147(2) 0.0417(9) Uani 1 1 d . . . H9A H 0.7594 0.0349 -0.0319 0.063 Uiso 1 1 calc R . . H9B H 0.5832 0.0290 -0.0581 0.063 Uiso 1 1 calc R . . H9C H 0.6511 -0.0479 0.0022 0.063 Uiso 1 1 calc R . . C10 C 0.3370(4) 0.1917(2) -0.04047(17) 0.0275(7) Uani 1 1 d . . . H10A H 0.2665 0.2052 -0.0837 0.041 Uiso 1 1 calc R . . H10B H 0.4424 0.1883 -0.0604 0.041 Uiso 1 1 calc R . . H10C H 0.3296 0.2429 -0.0015 0.041 Uiso 1 1 calc R . . C11 C 0.1240(3) 0.0930(2) 0.0191(2) 0.0303(7) Uani 1 1 d . . . H11A H 0.1022 0.1436 0.0573 0.045 Uiso 1 1 calc R . . H11B H 0.0991 0.0304 0.0419 0.045 Uiso 1 1 calc R . . H11C H 0.0616 0.1033 -0.0278 0.045 Uiso 1 1 calc R . . C12 C -0.0422(4) 0.1904(3) 0.2646(2) 0.0408(9) Uani 1 1 d . . . H12A H -0.1405 0.2219 0.2755 0.061 Uiso 1 1 calc R . . H12B H -0.0552 0.1207 0.2674 0.061 Uiso 1 1 calc R . . H12C H -0.0069 0.2083 0.2122 0.061 Uiso 1 1 calc R . . C13 C 0.1031(5) 0.3301(2) 0.3232(2) 0.0427(9) Uani 1 1 d . . . H13A H 0.1434 0.3484 0.2719 0.064 Uiso 1 1 calc R . . H13B H 0.1770 0.3485 0.3638 0.064 Uiso 1 1 calc R . . H13C H 0.0054 0.3631 0.3324 0.064 Uiso 1 1 calc R . . C14 C 0.3310(5) 0.2024(3) 0.46580(18) 0.0381(8) Uani 1 1 d . . . H14A H 0.2994 0.1376 0.4813 0.057 Uiso 1 1 calc R . . H14B H 0.2422 0.2455 0.4680 0.057 Uiso 1 1 calc R . . H14C H 0.4108 0.2256 0.5014 0.057 Uiso 1 1 calc R . . C15 C 0.5400(4) 0.1412(3) 0.3761(2) 0.0440(9) Uani 1 1 d . . . H15A H 0.6184 0.1686 0.4106 0.066 Uiso 1 1 calc R . . H15B H 0.5772 0.1422 0.3221 0.066 Uiso 1 1 calc R . . H15C H 0.5187 0.0749 0.3917 0.066 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 0.0244(2) 0.0141(2) 0.0117(2) -0.00009(17) 0.00182(18) -0.0008(2) Br1 0.0520(2) 0.01826(14) 0.02060(15) -0.00188(11) 0.00850(15) -0.01187(16) P1 0.0199(3) 0.0152(3) 0.0130(3) -0.0011(2) 0.0014(3) 0.0002(3) P2 0.0256(3) 0.0169(3) 0.0125(3) -0.0006(2) 0.0024(3) -0.0015(3) O1 0.0376(12) 0.0152(9) 0.0189(10) -0.0015(7) 0.0043(9) 0.0027(9) O2 0.0492(14) 0.0192(10) 0.0166(11) -0.0010(8) 0.0091(9) -0.0056(10) C1 0.0392(16) 0.0172(13) 0.0226(15) 0.0023(12) 0.0056(14) 0.0028(14) C2 0.068(3) 0.0196(15) 0.0281(18) 0.0020(13) 0.0126(17) -0.0033(18) C3 0.0462(19) 0.0171(13) 0.0221(15) 0.0004(11) 0.0058(14) -0.0007(14) C4 0.0213(15) 0.0286(15) 0.0293(16) -0.0047(12) 0.0077(12) -0.0022(13) C5 0.0282(15) 0.0182(13) 0.0137(13) -0.0004(10) -0.0027(11) 0.0015(12) C6 0.0279(14) 0.0274(15) 0.0250(15) -0.0059(12) 0.0070(13) 0.0028(14) C7 0.0340(17) 0.0323(16) 0.0137(13) -0.0013(11) -0.0031(12) -0.0115(16) C8 0.0200(15) 0.049(2) 0.046(2) -0.0078(18) -0.0058(14) 0.0053(16) C9 0.0311(17) 0.050(2) 0.044(2) -0.0169(17) 0.0156(16) -0.0005(19) C10 0.0429(18) 0.0217(15) 0.0178(15) 0.0009(11) -0.0026(14) 0.0021(15) C11 0.0262(17) 0.0373(18) 0.0275(16) -0.0014(13) -0.0034(12) 0.0059(14) C12 0.0236(17) 0.053(2) 0.046(2) -0.0069(17) -0.0019(14) 0.0064(17) C13 0.051(2) 0.0278(16) 0.049(2) -0.0035(15) 0.007(2) 0.0097(17) C14 0.053(2) 0.045(2) 0.0159(16) -0.0046(14) -0.0010(15) -0.015(2) C15 0.0382(19) 0.061(3) 0.0327(19) -0.0044(18) -0.0107(15) 0.001(2) _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 Ni1 C2 . . 1.964(3) Y Ni1 P2 . . 2.1527(8) Y Ni1 P1 . . 2.1574(8) Y Ni1 Br1 . . 2.3458(5) Y P1 O1 . . 1.635(2) Y P1 C4 . . 1.829(3) Y P1 C5 . . 1.830(3) Y P2 O2 . . 1.630(2) Y P2 C6 . . 1.833(3) Y P2 C7 . . 1.840(3) Y O1 C1 . . 1.434(3) Y O2 C3 . . 1.435(3) Y C1 C2 . . 1.495(4) Y C1 H1a . . 0.99 ? C1 H1b . . 0.99 ? C2 C3 . . 1.480(4) Y C2 H2 . . 1 ? C3 H3a . . 0.99 ? C3 H3b . . 0.99 ? C4 C8 . . 1.520(5) Y C4 C9 . . 1.525(4) Y C4 H4 . . 1 ? C5 C11 . . 1.528(4) Y C5 C10 . . 1.532(4) Y C5 H5 . . 1 ? C6 C13 . . 1.515(4) Y C6 C12 . . 1.545(4) Y C6 H6 . . 1 ? C7 C15 . . 1.511(5) Y C7 C14 . . 1.538(4) Y C7 H7 . . 1 ? C8 H8a . . 0.98 ? C8 H8b . . 0.98 ? C8 H8c . . 0.98 ? C9 H9a . . 0.98 ? C9 H9b . . 0.98 ? C9 H9c . . 0.98 ? C10 H10a . . 0.98 ? C10 H10b . . 0.98 ? C10 H10c . . 0.98 ? C11 H11a . . 0.98 ? C11 H11b . . 0.98 ? C11 H11c . . 0.98 ? C12 H12a . . 0.98 ? C12 H12b . . 0.98 ? C12 H12c . . 0.98 ? C13 H13a . . 0.98 ? C13 H13b . . 0.98 ? C13 H13c . . 0.98 ? C14 H14a . . 0.98 ? C14 H14b . . 0.98 ? C14 H14c . . 0.98 ? C15 H15a . . 0.98 ? C15 H15b . . 0.98 ? C15 H15c . . 0.98 ? 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 NI1 P2 . . . 83.28(10) Y C2 NI1 P1 . . . 83.28(10) Y P2 NI1 P1 . . . 166.50(3) Y C2 NI1 BR1 . . . 176.29(14) Y P2 NI1 BR1 . . . 96.36(3) Y P1 NI1 BR1 . . . 97.13(3) Y O1 P1 C4 . . . 103.64(13) Y O1 P1 C5 . . . 101.33(12) Y C4 P1 C5 . . . 106.01(14) Y O1 P1 NI1 . . . 107.14(8) Y C4 P1 NI1 . . . 118.35(10) Y C5 P1 NI1 . . . 118.09(10) Y O2 P2 C6 . . . 99.93(13) Y O2 P2 C7 . . . 104.28(13) Y C6 P2 C7 . . . 106.24(15) Y O2 P2 NI1 . . . 106.89(8) Y C6 P2 NI1 . . . 120.48(10) Y C7 P2 NI1 . . . 116.56(11) Y C1 O1 P1 . . . 112.25(17) Y C3 O2 P2 . . . 113.17(18) Y O1 C1 C2 . . . 114.3(2) Y O1 C1 H1A . . . 108.7 ? C2 C1 H1A . . . 108.7 ? O1 C1 H1B . . . 108.7 ? C2 C1 H1B . . . 108.7 ? H1A C1 H1B . . . 107.6 ? C3 C2 C1 . . . 112.9(3) Y C3 C2 NI1 . . . 115.6(2) Y C1 C2 NI1 . . . 113.9(2) Y C3 C2 H2 . . . 104.2 ? C1 C2 H2 . . . 104.2 ? NI1 C2 H2 . . . 104.2 ? O2 C3 C2 . . . 113.4(3) Y O2 C3 H3A . . . 108.9 ? C2 C3 H3A . . . 108.9 ? O2 C3 H3B . . . 108.9 ? C2 C3 H3B . . . 108.9 ? H3A C3 H3B . . . 107.7 ? C8 C4 C9 . . . 112.4(3) Y C8 C4 P1 . . . 109.5(2) Y C9 C4 P1 . . . 112.9(2) Y C8 C4 H4 . . . 107.2 ? C9 C4 H4 . . . 107.2 ? P1 C4 H4 . . . 107.2 ? C11 C5 C10 . . . 111.2(3) Y C11 C5 P1 . . . 109.6(2) Y C10 C5 P1 . . . 112.5(2) Y C11 C5 H5 . . . 107.8 ? C10 C5 H5 . . . 107.8 ? P1 C5 H5 . . . 107.8 ? C13 C6 C12 . . . 111.5(3) Y C13 C6 P2 . . . 112.8(2) Y C12 C6 P2 . . . 108.7(2) Y C13 C6 H6 . . . 107.8 ? C12 C6 H6 . . . 107.8 ? P2 C6 H6 . . . 107.8 ? C15 C7 C14 . . . 112.1(3) Y C15 C7 P2 . . . 108.7(2) Y C14 C7 P2 . . . 113.1(2) Y C15 C7 H7 . . . 107.5 ? C14 C7 H7 . . . 107.5 ? P2 C7 H7 . . . 107.5 ? C4 C8 H8A . . . 109.5 ? C4 C8 H8B . . . 109.5 ? H8A C8 H8B . . . 109.5 ? C4 C8 H8C . . . 109.5 ? H8A C8 H8C . . . 109.5 ? H8B C8 H8C . . . 109.5 ? C4 C9 H9A . . . 109.5 ? C4 C9 H9B . . . 109.5 ? H9A C9 H9B . . . 109.5 ? C4 C9 H9C . . . 109.5 ? H9A C9 H9C . . . 109.5 ? H9B C9 H9C . . . 109.5 ? C5 C10 H10A . . . 109.5 ? C5 C10 H10B . . . 109.5 ? H10A C10 H10B . . . 109.5 ? C5 C10 H10C . . . 109.5 ? H10A C10 H10C . . . 109.5 ? H10B C10 H10C . . . 109.5 ? C5 C11 H11A . . . 109.5 ? C5 C11 H11B . . . 109.5 ? H11A C11 H11B . . . 109.5 ? C5 C11 H11C . . . 109.5 ? H11A C11 H11C . . . 109.5 ? H11B C11 H11C . . . 109.5 ? C6 C12 H12A . . . 109.5 ? C6 C12 H12B . . . 109.5 ? H12A C12 H12B . . . 109.5 ? C6 C12 H12C . . . 109.5 ? H12A C12 H12C . . . 109.5 ? H12B C12 H12C . . . 109.5 ? C6 C13 H13A . . . 109.5 ? C6 C13 H13B . . . 109.5 ? H13A C13 H13B . . . 109.5 ? C6 C13 H13C . . . 109.5 ? H13A C13 H13C . . . 109.5 ? H13B C13 H13C . . . 109.5 ? C7 C14 H14A . . . 109.5 ? C7 C14 H14B . . . 109.5 ? H14A C14 H14B . . . 109.5 ? C7 C14 H14C . . . 109.5 ? H14A C14 H14C . . . 109.5 ? H14B C14 H14C . . . 109.5 ? C7 C15 H15A . . . 109.5 ? C7 C15 H15B . . . 109.5 ? H15A C15 H15B . . . 109.5 ? C7 C15 H15C . . . 109.5 ? H15A C15 H15C . . . 109.5 ? H15B C15 H15C . . . 109.5 ? 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 C2 NI1 P1 O1 . . . . -10.48(16) Y P2 NI1 P1 O1 . . . . -5.2(2) Y BR1 NI1 P1 O1 . . . . 173.23(9) Y C2 NI1 P1 C4 . . . . -127.02(18) Y P2 NI1 P1 C4 . . . . -121.69(19) Y BR1 NI1 P1 C4 . . . . 56.70(12) Y C2 NI1 P1 C5 . . . . 102.95(17) Y P2 NI1 P1 C5 . . . . 108.28(19) Y BR1 NI1 P1 C5 . . . . -73.34(11) Y C2 NI1 P2 O2 . . . . 6.55(16) Y P1 NI1 P2 O2 . . . . 1.2(2) Y BR1 NI1 P2 O2 . . . . -177.17(9) Y C2 NI1 P2 C6 . . . . -106.27(18) Y P1 NI1 P2 C6 . . . . -111.60(19) Y BR1 NI1 P2 C6 . . . . 70.01(12) Y C2 NI1 P2 C7 . . . . 122.66(18) Y P1 NI1 P2 C7 . . . . 117.33(19) Y BR1 NI1 P2 C7 . . . . -61.06(12) Y C4 P1 O1 C1 . . . . 120.7(2) Y C5 P1 O1 C1 . . . . -129.5(2) Y NI1 P1 O1 C1 . . . . -5.2(2) Y C6 P2 O2 C3 . . . . 134.8(2) Y C7 P2 O2 C3 . . . . -115.4(2) Y NI1 P2 O2 C3 . . . . 8.6(2) Y P1 O1 C1 C2 . . . . 24.7(4) Y O1 C1 C2 C3 . . . . -169.7(3) Y O1 C1 C2 NI1 . . . . -35.2(4) Y P2 NI1 C2 C3 . . . . -21.0(3) Y P1 NI1 C2 C3 . . . . 157.8(3) Y P2 NI1 C2 C1 . . . . -154.2(3) Y P1 NI1 C2 C1 . . . . 24.5(3) Y P2 O2 C3 C2 . . . . -25.2(4) Y C1 C2 C3 O2 . . . . 166.0(3) Y NI1 C2 C3 O2 . . . . 32.3(4) Y O1 P1 C4 C8 . . . . -78.4(2) Y C5 P1 C4 C8 . . . . 175.4(2) Y NI1 P1 C4 C8 . . . . 40.0(3) Y O1 P1 C4 C9 . . . . 47.7(3) Y C5 P1 C4 C9 . . . . -58.6(3) Y NI1 P1 C4 C9 . . . . 166.1(2) Y O1 P1 C5 C11 . . . . 76.9(2) Y C4 P1 C5 C11 . . . . -175.2(2) Y NI1 P1 C5 C11 . . . . -39.7(2) Y O1 P1 C5 C10 . . . . -158.9(2) Y C4 P1 C5 C10 . . . . -51.0(2) Y NI1 P1 C5 C10 . . . . 84.5(2) Y O2 P2 C6 C13 . . . . 161.5(2) Y C7 P2 C6 C13 . . . . 53.4(3) Y NI1 P2 C6 C13 . . . . -82.0(2) Y O2 P2 C6 C12 . . . . -74.2(2) Y C7 P2 C6 C12 . . . . 177.6(2) Y NI1 P2 C6 C12 . . . . 42.3(3) Y O2 P2 C7 C15 . . . . 71.0(3) Y C6 P2 C7 C15 . . . . 176.0(2) Y NI1 P2 C7 C15 . . . . -46.6(3) Y O2 P2 C7 C14 . . . . -54.3(3) Y C6 P2 C7 C14 . . . . 50.8(3) Y NI1 P2 C7 C14 . . . . -171.8(2) Y _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 72.85 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.899 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.084 # Attachment 'valer7.cif' data_valer7 _database_code_depnum_ccdc_archive 'CCDC 620342' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H31 Br Ni O2 P2' _chemical_formula_sum 'C18 H31 Br Ni O2 P2' _chemical_formula_weight 479.99 _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' Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.9840(3) _cell_length_b 13.0363(3) _cell_length_c 13.4366(3) _cell_angle_alpha 78.494(2) _cell_angle_beta 77.305(1) _cell_angle_gamma 88.467(2) _cell_volume 2173.79(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5788 _cell_measurement_theta_min 3.44 _cell_measurement_theta_max 72.61 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 4.889 _exptl_absorpt_correction_Type multi-scan _exptl_absorpt_correction_T_min 0.590 _exptl_absorpt_correction_T_max 0.870 _exptl_absorpt_process_details 'Sadabs (Sheldrick,1996)' _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 Platform diffractometer, equipped with a Bruker SMART 2K Charged-Coupled Device (CCD) Area Detector using the program SMART and normal focus sealed tube source graphite monochromated Cu-K\a radiation. The crystal-to-detector distance was 4.908 cm, and the data collection was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 9.0 degree scan in 30 frames over four different parts of the reciprocal space (120 frames total). One complete sphere of data was collected, to better than 0.8\%A resolution. Upon completion of the data collection, the first 101 frames were recollected in order to improve the decay correction analysis. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart 2000' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.5 _diffrn_standards_number 188 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% -0.05 _diffrn_reflns_number 26424 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_av_sigmaI/netI 0.0459 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 72.99 _reflns_number_total 8305 _reflns_number_gt 6456 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1999)' _computing_cell_refinement 'SMART (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'UdMX (local program)' _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^)+(0.0463P)^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 8305 _refine_ls_number_parameters 449 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0875 _refine_ls_wR_factor_gt 0.0840 _refine_ls_goodness_of_fit_ref 0.976 _refine_ls_restrained_S_all 0.976 _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 Ni11 Ni 0.05357(3) 0.26057(3) 0.20342(4) 0.01470(11) Uani 1 1 d . . . Br11 Br 0.22502(2) 0.25266(2) 0.22911(3) 0.02375(9) Uani 1 1 d . . . P11 P 0.05192(5) 0.12061(5) 0.14149(5) 0.01515(15) Uani 1 1 d . . . P12 P 0.01231(6) 0.40014(5) 0.26336(6) 0.01576(15) Uani 1 1 d . . . O11 O -0.06680(15) 0.11426(15) 0.11520(15) 0.0203(4) Uani 1 1 d . . . O12 O -0.10844(15) 0.42958(15) 0.24752(16) 0.0214(4) Uani 1 1 d . . . C11 C -0.1505(2) 0.3547(2) 0.2065(2) 0.0175(6) Uani 1 1 d . . . C12 C -0.0852(2) 0.2719(2) 0.1816(2) 0.0159(6) Uani 1 1 d . . . C13 C -0.1288(2) 0.1978(2) 0.1406(2) 0.0174(6) Uani 1 1 d . . . C14 C -0.2301(2) 0.2050(2) 0.1221(2) 0.0228(6) Uani 1 1 d . . . H14 H -0.2569 0.1542 0.0922 0.027 Uiso 1 1 calc R . . C15 C -0.2913(2) 0.2889(2) 0.1488(2) 0.0252(7) Uani 1 1 d . . . H15 H -0.3613 0.2942 0.1380 0.030 Uiso 1 1 calc R . . C16 C -0.2522(2) 0.3651(2) 0.1908(2) 0.0225(6) Uani 1 1 d . . . H16 H -0.2942 0.4224 0.2082 0.027 Uiso 1 1 calc R . . C17 C 0.0597(2) -0.0034(2) 0.2299(2) 0.0181(6) Uani 1 1 d . . . H17 H 0.1347 -0.0128 0.2368 0.022 Uiso 1 1 calc R . . C18 C 0.1371(2) 0.1114(2) 0.0161(2) 0.0207(6) Uani 1 1 d . . . H18 H 0.1062 0.0573 -0.0126 0.025 Uiso 1 1 calc R . . C19 C -0.0047(2) 0.3931(2) 0.4034(2) 0.0229(7) Uani 1 1 d . . . H19 H -0.0493 0.4533 0.4216 0.027 Uiso 1 1 calc R . . C110 C 0.0886(2) 0.5189(2) 0.1976(2) 0.0170(6) Uani 1 1 d . . . H110 H 0.1608 0.5097 0.2124 0.020 Uiso 1 1 calc R . . C111 C 0.0275(2) -0.0967(2) 0.1903(2) 0.0237(7) Uani 1 1 d . . . H11A H 0.0372 -0.1616 0.2383 0.036 Uiso 1 1 calc R . . H11B H 0.0714 -0.0976 0.1211 0.036 Uiso 1 1 calc R . . H11C H -0.0469 -0.0908 0.1860 0.036 Uiso 1 1 calc R . . C112 C -0.0083(2) 0.0015(2) 0.3376(2) 0.0271(7) Uani 1 1 d . . . H11D H -0.0817 0.0147 0.3321 0.041 Uiso 1 1 calc R . . H11E H 0.0180 0.0581 0.3641 0.041 Uiso 1 1 calc R . . H11F H -0.0048 -0.0653 0.3854 0.041 Uiso 1 1 calc R . . C113 C 0.2495(2) 0.0793(3) 0.0251(2) 0.0291(7) Uani 1 1 d . . . H11G H 0.2945 0.0847 -0.0447 0.044 Uiso 1 1 calc R . . H11H H 0.2484 0.0069 0.0635 0.044 Uiso 1 1 calc R . . H11I H 0.2775 0.1257 0.0623 0.044 Uiso 1 1 calc R . . C114 C 0.1364(3) 0.2174(2) -0.0579(2) 0.0307(8) Uani 1 1 d . . . H11J H 0.1655 0.2718 -0.0305 0.046 Uiso 1 1 calc R . . H11K H 0.0637 0.2346 -0.0637 0.046 Uiso 1 1 calc R . . H11L H 0.1795 0.2136 -0.1267 0.046 Uiso 1 1 calc R . . C115 C 0.0991(3) 0.4031(3) 0.4353(2) 0.0309(8) Uani 1 1 d . . . H11M H 0.0862 0.3948 0.5112 0.046 Uiso 1 1 calc R . . H11N H 0.1311 0.4722 0.4025 0.046 Uiso 1 1 calc R . . H11O H 0.1470 0.3486 0.4130 0.046 Uiso 1 1 calc R . . C116 C -0.0658(3) 0.2920(3) 0.4624(3) 0.0382(9) Uani 1 1 d . . . H11P H -0.0215 0.2315 0.4513 0.057 Uiso 1 1 calc R . . H11Q H -0.1301 0.2869 0.4366 0.057 Uiso 1 1 calc R . . H11R H -0.0849 0.2930 0.5369 0.057 Uiso 1 1 calc R . . C117 C 0.1004(3) 0.5318(2) 0.0801(2) 0.0283(7) Uani 1 1 d . . . H11S H 0.0307 0.5411 0.0631 0.042 Uiso 1 1 calc R . . H11T H 0.1329 0.4692 0.0574 0.042 Uiso 1 1 calc R . . H11U H 0.1453 0.5933 0.0445 0.042 Uiso 1 1 calc R . . C118 C 0.0429(2) 0.6173(2) 0.2348(2) 0.0245(7) Uani 1 1 d . . . H11V H 0.0859 0.6784 0.1943 0.037 Uiso 1 1 calc R . . H11W H 0.0433 0.6106 0.3086 0.037 Uiso 1 1 calc R . . H11$ H -0.0297 0.6260 0.2253 0.037 Uiso 1 1 calc R . . Ni21 Ni 0.43914(4) 0.77105(4) 0.28443(4) 0.01553(11) Uani 1 1 d . . . Br21 Br 0.27667(2) 0.78791(3) 0.23735(3) 0.02683(9) Uani 1 1 d . . . P21 P 0.47355(6) 0.61584(5) 0.25449(6) 0.01608(15) Uani 1 1 d . . . P22 P 0.44059(6) 0.91823(6) 0.33467(6) 0.01703(15) Uani 1 1 d . . . O21 O 0.59145(15) 0.58798(15) 0.27989(16) 0.0215(4) Uani 1 1 d . . . O22 O 0.55852(15) 0.92885(15) 0.36053(16) 0.0228(5) Uani 1 1 d . . . C21 C 0.6349(2) 0.6712(2) 0.3085(2) 0.0175(6) Uani 1 1 d . . . C22 C 0.5733(2) 0.7595(2) 0.3174(2) 0.0164(6) Uani 1 1 d . . . C26 C 0.7365(2) 0.6630(2) 0.3256(2) 0.0201(6) Uani 1 1 d . . . H26 H 0.7768 0.6021 0.3174 0.024 Uiso 1 1 calc R . . C25 C 0.7775(2) 0.7466(2) 0.3552(2) 0.0217(6) Uani 1 1 d . . . H25 H 0.8472 0.7427 0.3669 0.026 Uiso 1 1 calc R . . C24 C 0.7192(2) 0.8359(2) 0.3681(2) 0.0222(6) Uani 1 1 d . . . H24 H 0.7476 0.8920 0.3897 0.027 Uiso 1 1 calc R . . C23 C 0.6184(2) 0.8407(2) 0.3483(2) 0.0188(6) Uani 1 1 d . . . C27 C 0.4944(2) 0.5871(2) 0.1237(2) 0.0223(6) Uani 1 1 d . . . H27 H 0.5353 0.5210 0.1233 0.027 Uiso 1 1 calc R . . C28 C 0.3876(2) 0.5113(2) 0.3417(2) 0.0218(6) Uani 1 1 d . . . H28 H 0.3213 0.5116 0.3153 0.026 Uiso 1 1 calc R . . C29 C 0.4339(2) 1.0392(2) 0.2411(2) 0.0201(6) Uani 1 1 d . . . H29 H 0.3596 1.0464 0.2316 0.024 Uiso 1 1 calc R . . C210 C 0.3531(2) 0.9332(2) 0.4573(2) 0.0244(7) Uani 1 1 d . . . H210 H 0.3814 0.9921 0.4815 0.029 Uiso 1 1 calc R . . C211 C 0.5624(3) 0.6756(3) 0.0473(3) 0.0411(9) Uani 1 1 d . . . H21A H 0.5818 0.6575 -0.0217 0.062 Uiso 1 1 calc R . . H21B H 0.6265 0.6855 0.0718 0.062 Uiso 1 1 calc R . . H21C H 0.5224 0.7406 0.0430 0.062 Uiso 1 1 calc R . . C212 C 0.3918(2) 0.5702(3) 0.0921(2) 0.0325(8) Uani 1 1 d . . . H21D H 0.3469 0.6312 0.0989 0.049 Uiso 1 1 calc R . . H21E H 0.3552 0.5075 0.1374 0.049 Uiso 1 1 calc R . . H21F H 0.4071 0.5612 0.0197 0.049 Uiso 1 1 calc R . . C213 C 0.4338(3) 0.4022(2) 0.3433(3) 0.0339(8) Uani 1 1 d . . . H21G H 0.5004 0.3994 0.3667 0.051 Uiso 1 1 calc R . . H21H H 0.4469 0.3869 0.2731 0.051 Uiso 1 1 calc R . . H21I H 0.3838 0.3502 0.3911 0.051 Uiso 1 1 calc R . . C214 C 0.3568(3) 0.5377(2) 0.4505(2) 0.0314(8) Uani 1 1 d . . . H21J H 0.3094 0.4827 0.4972 0.047 Uiso 1 1 calc R . . H21K H 0.3208 0.6049 0.4464 0.047 Uiso 1 1 calc R . . H21L H 0.4204 0.5422 0.4775 0.047 Uiso 1 1 calc R . . C215 C 0.5054(3) 1.0304(2) 0.1359(2) 0.0304(7) Uani 1 1 d . . . H21M H 0.5004 1.0943 0.0845 0.046 Uiso 1 1 calc R . . H21N H 0.4828 0.9699 0.1124 0.046 Uiso 1 1 calc R . . H21O H 0.5786 1.0215 0.1435 0.046 Uiso 1 1 calc R . . C216 C 0.4623(2) 1.1362(2) 0.2778(2) 0.0265(7) Uani 1 1 d . . . H21P H 0.5355 1.1317 0.2862 0.040 Uiso 1 1 calc R . . H21Q H 0.4150 1.1402 0.3446 0.040 Uiso 1 1 calc R . . H21R H 0.4547 1.1989 0.2261 0.040 Uiso 1 1 calc R . . C217 C 0.3546(3) 0.8329(3) 0.5396(2) 0.0349(8) Uani 1 1 d . . . H21S H 0.3103 0.8420 0.6064 0.052 Uiso 1 1 calc R . . H21T H 0.4272 0.8190 0.5476 0.052 Uiso 1 1 calc R . . H21U H 0.3272 0.7738 0.5175 0.052 Uiso 1 1 calc R . . C218 C 0.2415(2) 0.9605(3) 0.4434(2) 0.0294(7) Uani 1 1 d . . . H21V H 0.2151 0.9078 0.4120 0.044 Uiso 1 1 calc R . . H21W H 0.2424 1.0295 0.3980 0.044 Uiso 1 1 calc R . . H21$ H 0.1952 0.9617 0.5114 0.044 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 Ni11 0.0134(2) 0.0123(2) 0.0204(3) -0.00682(19) -0.00486(19) 0.00095(19) Br11 0.01583(16) 0.02605(17) 0.03529(19) -0.01529(14) -0.01039(13) 0.00525(13) P11 0.0158(3) 0.0126(3) 0.0188(4) -0.0064(3) -0.0048(3) 0.0002(3) P12 0.0154(3) 0.0122(3) 0.0208(4) -0.0063(3) -0.0038(3) 0.0010(3) O11 0.0202(10) 0.0162(10) 0.0289(12) -0.0094(8) -0.0104(9) 0.0016(8) O12 0.0157(10) 0.0153(10) 0.0343(12) -0.0084(9) -0.0049(9) 0.0034(8) C11 0.0145(14) 0.0141(13) 0.0222(15) -0.0013(11) -0.0022(11) -0.0024(11) C12 0.0138(13) 0.0128(13) 0.0194(15) -0.0018(11) -0.0016(11) 0.0011(11) C13 0.0155(14) 0.0141(13) 0.0224(15) -0.0025(11) -0.0043(11) -0.0004(11) C14 0.0206(15) 0.0197(15) 0.0300(17) -0.0031(12) -0.0104(13) -0.0049(13) C15 0.0151(14) 0.0254(16) 0.0339(18) 0.0019(13) -0.0092(13) -0.0031(13) C16 0.0147(14) 0.0185(15) 0.0317(17) -0.0010(12) -0.0031(12) 0.0014(12) C17 0.0169(14) 0.0146(14) 0.0231(15) -0.0041(11) -0.0049(12) 0.0016(12) C18 0.0232(15) 0.0218(15) 0.0167(15) -0.0080(12) 0.0006(12) -0.0032(13) C19 0.0293(17) 0.0184(15) 0.0205(15) -0.0088(12) -0.0003(13) 0.0000(13) C110 0.0150(14) 0.0136(13) 0.0233(15) -0.0048(11) -0.0054(12) -0.0007(11) C111 0.0279(16) 0.0138(14) 0.0295(17) -0.0057(12) -0.0054(14) 0.0008(13) C112 0.0314(17) 0.0236(16) 0.0234(17) -0.0017(13) -0.0022(14) -0.0016(14) C113 0.0242(17) 0.0334(18) 0.0277(18) -0.0138(14) 0.0058(14) -0.0003(14) C114 0.042(2) 0.0296(18) 0.0195(16) -0.0012(13) -0.0056(14) -0.0107(16) C115 0.0386(19) 0.0346(18) 0.0234(17) -0.0127(14) -0.0100(15) 0.0080(16) C116 0.055(2) 0.0288(18) 0.0254(18) -0.0045(14) 0.0036(17) -0.0130(17) C117 0.0366(19) 0.0224(16) 0.0225(17) -0.0001(13) -0.0031(14) -0.0035(14) C118 0.0271(16) 0.0162(15) 0.0314(18) -0.0069(13) -0.0069(14) -0.0002(13) Ni21 0.0142(2) 0.0149(2) 0.0202(3) -0.00746(19) -0.00613(19) 0.00126(19) Br21 0.01982(16) 0.02704(18) 0.0429(2) -0.01845(15) -0.01695(14) 0.00685(13) P21 0.0156(3) 0.0131(3) 0.0203(4) -0.0046(3) -0.0043(3) 0.0003(3) P22 0.0151(3) 0.0169(4) 0.0223(4) -0.0097(3) -0.0057(3) 0.0010(3) O21 0.0185(10) 0.0138(10) 0.0338(12) -0.0064(9) -0.0077(9) 0.0026(8) O22 0.0178(10) 0.0205(11) 0.0369(13) -0.0152(9) -0.0121(9) 0.0027(9) C21 0.0176(14) 0.0161(14) 0.0172(14) 0.0000(11) -0.0030(11) -0.0012(12) C22 0.0145(13) 0.0186(14) 0.0155(14) -0.0028(11) -0.0025(11) -0.0013(12) C26 0.0165(14) 0.0180(14) 0.0226(15) 0.0026(11) -0.0038(12) 0.0015(12) C25 0.0139(14) 0.0281(16) 0.0218(16) 0.0008(12) -0.0061(12) -0.0015(12) C24 0.0195(15) 0.0228(15) 0.0269(16) -0.0057(12) -0.0092(13) -0.0033(13) C23 0.0170(14) 0.0193(14) 0.0207(15) -0.0052(12) -0.0043(12) 0.0023(12) C27 0.0281(16) 0.0196(15) 0.0194(15) -0.0086(12) -0.0018(13) 0.0004(13) C28 0.0186(15) 0.0191(15) 0.0271(17) -0.0013(12) -0.0061(13) -0.0040(12) C29 0.0145(14) 0.0189(15) 0.0283(17) -0.0070(12) -0.0060(12) 0.0019(12) C210 0.0238(16) 0.0295(17) 0.0236(16) -0.0149(13) -0.0040(13) -0.0017(14) C211 0.052(2) 0.040(2) 0.0246(18) -0.0076(15) 0.0074(17) -0.0084(18) C212 0.0361(19) 0.040(2) 0.0298(18) -0.0196(15) -0.0141(15) 0.0100(16) C213 0.041(2) 0.0143(15) 0.043(2) -0.0024(14) -0.0053(17) -0.0052(15) C214 0.0368(19) 0.0288(17) 0.0239(17) 0.0033(13) -0.0037(14) -0.0046(15) C215 0.0348(19) 0.0253(17) 0.0276(18) -0.0044(13) -0.0005(15) 0.0033(15) C216 0.0221(16) 0.0193(15) 0.040(2) -0.0097(14) -0.0069(14) 0.0006(13) C217 0.039(2) 0.044(2) 0.0207(17) -0.0066(15) -0.0044(15) -0.0041(17) C218 0.0203(16) 0.0393(19) 0.0309(18) -0.0182(15) -0.0004(14) 0.0020(14) _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 Ni11 C12 . . 1.885(3) Y Ni11 P12 . . 2.1422(8) Y Ni11 P11 . . 2.1534(8) Y Ni11 Br11 . . 2.3231(5) Y P11 O11 . . 1.6631(19) Y P11 C17 . . 1.820(3) Y P11 C18 . . 1.825(3) Y P12 O12 . . 1.653(2) Y P12 C110 . . 1.819(3) Y P12 C19 . . 1.830(3) Y O11 C13 . . 1.390(3) Y O12 C11 . . 1.389(3) Y C11 C16 . . 1.382(4) Y C11 C12 . . 1.403(4) Y C12 C13 . . 1.390(4) Y C13 C14 . . 1.389(4) Y C14 C15 . . 1.392(4) Y C14 H14 . . 0.95 ? C15 C16 . . 1.393(4) Y C15 H15 . . 0.95 ? C16 H16 . . 0.95 ? C17 C111 . . 1.523(4) Y C17 C112 . . 1.533(4) Y C17 H17 . . 1 ? C18 C113 . . 1.531(4) Y C18 C114 . . 1.534(4) Y C18 H18 . . 1 ? C19 C115 . . 1.517(4) Y C19 C116 . . 1.536(4) Y C19 H19 . . 1 ? C110 C118 . . 1.527(4) Y C110 C117 . . 1.527(4) Y C110 H110 . . 1 ? C111 H11a . . 0.98 ? C111 H11b . . 0.98 ? C111 H11c . . 0.98 ? C112 H11d . . 0.98 ? C112 H11e . . 0.98 ? C112 H11f . . 0.98 ? C113 H11g . . 0.98 ? C113 H11h . . 0.98 ? C113 H11i . . 0.98 ? C114 H11j . . 0.98 ? C114 H11k . . 0.98 ? C114 H11l . . 0.98 ? C115 H11m . . 0.98 ? C115 H11n . . 0.98 ? C115 H11o . . 0.98 ? C116 H11p . . 0.98 ? C116 H11q . . 0.98 ? C116 H11r . . 0.98 ? C117 H11s . . 0.98 ? C117 H11t . . 0.98 ? C117 H11u . . 0.98 ? C118 H11v . . 0.98 ? C118 H11w . . 0.98 ? C118 H11$ . . 0.98 ? Ni21 C22 . . 1.884(3) Y Ni21 P21 . . 2.1570(8) Y Ni21 P22 . . 2.1591(8) Y Ni21 Br21 . . 2.3247(5) Y P21 O21 . . 1.656(2) Y P21 C28 . . 1.829(3) Y P21 C27 . . 1.831(3) Y P22 O22 . . 1.6579(19) Y P22 C29 . . 1.823(3) Y P22 C210 . . 1.826(3) Y O21 C21 . . 1.393(3) Y O22 C23 . . 1.387(3) Y C21 C26 . . 1.386(4) Y C21 C22 . . 1.394(4) Y C22 C23 . . 1.397(4) Y C26 C25 . . 1.388(4) Y C26 H26 . . 0.95 ? C25 C24 . . 1.390(4) Y C25 H25 . . 0.95 ? C24 C23 . . 1.389(4) Y C24 H24 . . 0.95 ? C27 C212 . . 1.518(4) Y C27 C211 . . 1.533(4) Y C27 H27 . . 1 ? C28 C213 . . 1.527(4) Y C28 C214 . . 1.534(4) Y C28 H28 . . 1 ? C29 C216 . . 1.527(4) Y C29 C215 . . 1.535(4) Y C29 H29 . . 1 ? C210 C218 . . 1.525(4) Y C210 C217 . . 1.538(4) Y C210 H210 . . 1 ? C211 H21a . . 0.98 ? C211 H21b . . 0.98 ? C211 H21c . . 0.98 ? C212 H21d . . 0.98 ? C212 H21e . . 0.98 ? C212 H21f . . 0.98 ? C213 H21g . . 0.98 ? C213 H21h . . 0.98 ? C213 H21i . . 0.98 ? C214 H21j . . 0.98 ? C214 H21k . . 0.98 ? C214 H21l . . 0.98 ? C215 H21m . . 0.98 ? C215 H21n . . 0.98 ? C215 H21o . . 0.98 ? C216 H21p . . 0.98 ? C216 H21q . . 0.98 ? C216 H21r . . 0.98 ? C217 H21s . . 0.98 ? C217 H21t . . 0.98 ? C217 H21u . . 0.98 ? C218 H21v . . 0.98 ? C218 H21w . . 0.98 ? C218 H21$ . . 0.98 ? 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 C12 NI11 P12 . . . 82.32(9) Y C12 NI11 P11 . . . 82.71(9) Y P12 NI11 P11 . . . 164.92(4) Y C12 NI11 BR11 . . . 178.10(8) Y P12 NI11 BR11 . . . 96.11(3) Y P11 NI11 BR11 . . . 98.88(3) Y O11 P11 C17 . . . 103.19(11) Y O11 P11 C18 . . . 100.96(12) Y C17 P11 C18 . . . 107.12(13) Y O11 P11 NI11 . . . 105.87(7) Y C17 P11 NI11 . . . 116.81(9) Y C18 P11 NI11 . . . 120.27(10) Y O12 P12 C110 . . . 103.48(11) Y O12 P12 C19 . . . 101.01(12) Y C110 P12 C19 . . . 107.21(13) Y O12 P12 NI11 . . . 106.69(8) Y C110 P12 NI11 . . . 117.63(9) Y C19 P12 NI11 . . . 118.43(10) Y C13 O11 P11 . . . 111.60(17) Y C11 O12 P12 . . . 111.68(17) Y C16 C11 O12 . . . 119.6(2) Y C16 C11 C12 . . . 123.2(3) Y O12 C11 C12 . . . 117.2(2) Y C13 C12 C11 . . . 116.3(2) Y C13 C12 NI11 . . . 121.7(2) Y C11 C12 NI11 . . . 122.0(2) Y C14 C13 O11 . . . 118.9(3) Y C14 C13 C12 . . . 123.0(3) Y O11 C13 C12 . . . 118.1(2) Y C13 C14 C15 . . . 118.1(3) Y C13 C14 H14 . . . 121 ? C15 C14 H14 . . . 121 ? C14 C15 C16 . . . 121.6(3) Y C14 C15 H15 . . . 119.2 ? C16 C15 H15 . . . 119.2 ? C11 C16 C15 . . . 117.9(3) Y C11 C16 H16 . . . 121 ? C15 C16 H16 . . . 121 ? C111 C17 C112 . . . 111.0(2) Y C111 C17 P11 . . . 112.7(2) Y C112 C17 P11 . . . 109.14(19) Y C111 C17 H17 . . . 107.9 ? C112 C17 H17 . . . 107.9 ? P11 C17 H17 . . . 107.9 ? C113 C18 C114 . . . 111.5(2) Y C113 C18 P11 . . . 112.5(2) Y C114 C18 P11 . . . 107.9(2) Y C113 C18 H18 . . . 108.2 ? C114 C18 H18 . . . 108.2 ? P11 C18 H18 . . . 108.2 ? C115 C19 C116 . . . 112.3(3) Y C115 C19 P12 . . . 112.7(2) Y C116 C19 P12 . . . 109.1(2) Y C115 C19 H19 . . . 107.5 ? C116 C19 H19 . . . 107.5 ? P12 C19 H19 . . . 107.5 ? C118 C110 C117 . . . 110.7(2) Y C118 C110 P12 . . . 113.74(19) Y C117 C110 P12 . . . 109.50(19) Y C118 C110 H110 . . . 107.5 ? C117 C110 H110 . . . 107.5 ? P12 C110 H110 . . . 107.5 ? C17 C111 H11A . . . 109.5 ? C17 C111 H11B . . . 109.5 ? H11A C111 H11B . . . 109.5 ? C17 C111 H11C . . . 109.5 ? H11A C111 H11C . . . 109.5 ? H11B C111 H11C . . . 109.5 ? C17 C112 H11D . . . 109.5 ? C17 C112 H11E . . . 109.5 ? H11D C112 H11E . . . 109.5 ? C17 C112 H11F . . . 109.5 ? H11D C112 H11F . . . 109.5 ? H11E C112 H11F . . . 109.5 ? C18 C113 H11G . . . 109.5 ? C18 C113 H11H . . . 109.5 ? H11G C113 H11H . . . 109.5 ? C18 C113 H11I . . . 109.5 ? H11G C113 H11I . . . 109.5 ? H11H C113 H11I . . . 109.5 ? C18 C114 H11J . . . 109.5 ? C18 C114 H11K . . . 109.5 ? H11J C114 H11K . . . 109.5 ? C18 C114 H11L . . . 109.5 ? H11J C114 H11L . . . 109.5 ? H11K C114 H11L . . . 109.5 ? C19 C115 H11M . . . 109.5 ? C19 C115 H11N . . . 109.5 ? H11M C115 H11N . . . 109.5 ? C19 C115 H11O . . . 109.5 ? H11M C115 H11O . . . 109.5 ? H11N C115 H11O . . . 109.5 ? C19 C116 H11P . . . 109.5 ? C19 C116 H11Q . . . 109.5 ? H11P C116 H11Q . . . 109.5 ? C19 C116 H11R . . . 109.5 ? H11P C116 H11R . . . 109.5 ? H11Q C116 H11R . . . 109.5 ? C110 C117 H11S . . . 109.5 ? C110 C117 H11T . . . 109.5 ? H11S C117 H11T . . . 109.5 ? C110 C117 H11U . . . 109.5 ? H11S C117 H11U . . . 109.5 ? H11T C117 H11U . . . 109.5 ? C110 C118 H11V . . . 109.5 ? C110 C118 H11W . . . 109.5 ? H11V C118 H11W . . . 109.5 ? C110 C118 H11$ . . . 109.5 ? H11V C118 H11$ . . . 109.5 ? H11W C118 H11$ . . . 109.5 ? C22 NI21 P21 . . . 82.48(9) Y C22 NI21 P22 . . . 82.36(9) Y P21 NI21 P22 . . . 164.38(4) Y C22 NI21 BR21 . . . 177.88(8) Y P21 NI21 BR21 . . . 97.49(3) Y P22 NI21 BR21 . . . 97.80(3) Y O21 P21 C28 . . . 103.86(12) Y O21 P21 C27 . . . 100.19(12) Y C28 P21 C27 . . . 106.63(13) Y O21 P21 NI21 . . . 105.99(7) Y C28 P21 NI21 . . . 115.23(10) Y C27 P21 NI21 . . . 122.31(10) Y O22 P22 C29 . . . 102.28(12) Y O22 P22 C210 . . . 101.62(12) Y C29 P22 C210 . . . 106.78(14) Y O22 P22 NI21 . . . 106.02(7) Y C29 P22 NI21 . . . 118.6(1) Y C210 P22 NI21 . . . 118.82(10) Y C21 O21 P21 . . . 111.85(17) Y C23 O22 P22 . . . 111.71(17) Y C26 C21 O21 . . . 119.0(2) Y C26 C21 C22 . . . 123.5(3) Y O21 C21 C22 . . . 117.5(2) Y C21 C22 C23 . . . 116.1(3) Y C21 C22 NI21 . . . 122.0(2) Y C23 C22 NI21 . . . 121.9(2) Y C21 C26 C25 . . . 117.8(3) Y C21 C26 H26 . . . 121.1 ? C25 C26 H26 . . . 121.1 ? C26 C25 C24 . . . 121.7(3) Y C26 C25 H25 . . . 119.2 ? C24 C25 H25 . . . 119.2 ? C23 C24 C25 . . . 118.1(3) Y C23 C24 H24 . . . 120.9 ? C25 C24 H24 . . . 120.9 ? O22 C23 C24 . . . 119.4(3) Y O22 C23 C22 . . . 117.8(2) Y C24 C23 C22 . . . 122.8(3) Y C212 C27 C211 . . . 112.1(3) Y C212 C27 P21 . . . 112.8(2) Y C211 C27 P21 . . . 108.3(2) Y C212 C27 H27 . . . 107.8 ? C211 C27 H27 . . . 107.8 ? P21 C27 H27 . . . 107.8 ? C213 C28 C214 . . . 112.6(3) Y C213 C28 P21 . . . 113.8(2) Y C214 C28 P21 . . . 109.1(2) Y C213 C28 H28 . . . 107 ? C214 C28 H28 . . . 107 ? P21 C28 H28 . . . 107 ? C216 C29 C215 . . . 111.2(2) Y C216 C29 P22 . . . 112.9(2) Y C215 C29 P22 . . . 109.0(2) Y C216 C29 H29 . . . 107.9 ? C215 C29 H29 . . . 107.9 ? P22 C29 H29 . . . 107.9 ? C218 C210 C217 . . . 111.9(3) Y C218 C210 P22 . . . 111.5(2) Y C217 C210 P22 . . . 109.4(2) Y C218 C210 H210 . . . 108 ? C217 C210 H210 . . . 108 ? P22 C210 H210 . . . 108 ? C27 C211 H21A . . . 109.5 ? C27 C211 H21B . . . 109.5 ? H21A C211 H21B . . . 109.5 ? C27 C211 H21C . . . 109.5 ? H21A C211 H21C . . . 109.5 ? H21B C211 H21C . . . 109.5 ? C27 C212 H21D . . . 109.5 ? C27 C212 H21E . . . 109.5 ? H21D C212 H21E . . . 109.5 ? C27 C212 H21F . . . 109.5 ? H21D C212 H21F . . . 109.5 ? H21E C212 H21F . . . 109.5 ? C28 C213 H21G . . . 109.5 ? C28 C213 H21H . . . 109.5 ? H21G C213 H21H . . . 109.5 ? C28 C213 H21I . . . 109.5 ? H21G C213 H21I . . . 109.5 ? H21H C213 H21I . . . 109.5 ? C28 C214 H21J . . . 109.5 ? C28 C214 H21K . . . 109.5 ? H21J C214 H21K . . . 109.5 ? C28 C214 H21L . . . 109.5 ? H21J C214 H21L . . . 109.5 ? H21K C214 H21L . . . 109.5 ? C29 C215 H21M . . . 109.5 ? C29 C215 H21N . . . 109.5 ? H21M C215 H21N . . . 109.5 ? C29 C215 H21O . . . 109.5 ? H21M C215 H21O . . . 109.5 ? H21N C215 H21O . . . 109.5 ? C29 C216 H21P . . . 109.5 ? C29 C216 H21Q . . . 109.5 ? H21P C216 H21Q . . . 109.5 ? C29 C216 H21R . . . 109.5 ? H21P C216 H21R . . . 109.5 ? H21Q C216 H21R . . . 109.5 ? C210 C217 H21S . . . 109.5 ? C210 C217 H21T . . . 109.5 ? H21S C217 H21T . . . 109.5 ? C210 C217 H21U . . . 109.5 ? H21S C217 H21U . . . 109.5 ? H21T C217 H21U . . . 109.5 ? C210 C218 H21V . . . 109.5 ? C210 C218 H21W . . . 109.5 ? H21V C218 H21W . . . 109.5 ? C210 C218 H21$ . . . 109.5 ? H21V C218 H21$ . . . 109.5 ? H21W C218 H21$ . . . 109.5 ? 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 C12 NI11 P11 O11 . . . . 0.20(11) Y P12 NI11 P11 O11 . . . . 7.22(17) Y BR11 NI11 P11 O11 . . . . -178.76(8) Y C12 NI11 P11 C17 . . . . -113.96(13) Y P12 NI11 P11 C17 . . . . -106.94(17) Y BR11 NI11 P11 C17 . . . . 67.08(11) Y C12 NI11 P11 C18 . . . . 113.45(14) Y P12 NI11 P11 C18 . . . . 120.46(17) Y BR11 NI11 P11 C18 . . . . -65.51(12) Y C12 NI11 P12 O12 . . . . -2.37(11) Y P11 NI11 P12 O12 . . . . -9.40(17) Y BR11 NI11 P12 O12 . . . . 176.54(8) Y C12 NI11 P12 C110 . . . . -117.94(13) Y P11 NI11 P12 C110 . . . . -124.96(16) Y BR11 NI11 P12 C110 . . . . 60.97(11) Y C12 NI11 P12 C19 . . . . 110.52(14) Y P11 NI11 P12 C19 . . . . 103.50(17) Y BR11 NI11 P12 C19 . . . . -70.57(12) Y C17 P11 O11 C13 . . . . 122.85(19) Y C18 P11 O11 C13 . . . . -126.46(19) Y NI11 P11 O11 C13 . . . . -0.39(19) Y C110 P12 O12 C11 . . . . 128.08(19) Y C19 P12 O12 C11 . . . . -121.03(19) Y NI11 P12 O12 C11 . . . . 3.35(19) Y P12 O12 C11 C16 . . . . 178.2(2) Y P12 O12 C11 C12 . . . . -2.7(3) Y C16 C11 C12 C13 . . . . -0.9(4) Y O12 C11 C12 C13 . . . . -179.9(2) Y C16 C11 C12 NI11 . . . . 179.7(2) Y O12 C11 C12 NI11 . . . . 0.6(4) Y P12 NI11 C12 C13 . . . . -178.2(2) Y P11 NI11 C12 C13 . . . . 0.0(2) Y P12 NI11 C12 C11 . . . . 1.2(2) Y P11 NI11 C12 C11 . . . . 179.4(2) Y P11 O11 C13 C14 . . . . 179.2(2) Y P11 O11 C13 C12 . . . . 0.4(3) Y C11 C12 C13 C14 . . . . 1.6(4) Y NI11 C12 C13 C14 . . . . -179.0(2) Y C11 C12 C13 O11 . . . . -179.7(2) Y NI11 C12 C13 O11 . . . . -0.3(4) Y O11 C13 C14 C15 . . . . 179.5(3) Y C12 C13 C14 C15 . . . . -1.8(4) Y C13 C14 C15 C16 . . . . 1.3(4) Y O12 C11 C16 C15 . . . . 179.5(2) Y C12 C11 C16 C15 . . . . 0.5(4) Y C14 C15 C16 C11 . . . . -0.6(4) Y O11 P11 C17 C111 . . . . 48.3(2) Y C18 P11 C17 C111 . . . . -57.8(2) Y NI11 P11 C17 C111 . . . . 163.91(17) Y O11 P11 C17 C112 . . . . -75.5(2) Y C18 P11 C17 C112 . . . . 178.4(2) Y NI11 P11 C17 C112 . . . . 40.1(2) Y O11 P11 C18 C113 . . . . -161.1(2) Y C17 P11 C18 C113 . . . . -53.5(2) Y NI11 P11 C18 C113 . . . . 83.1(2) Y O11 P11 C18 C114 . . . . 75.4(2) Y C17 P11 C18 C114 . . . . -176.97(19) Y NI11 P11 C18 C114 . . . . -40.4(2) Y O12 P12 C19 C115 . . . . -160.8(2) Y C110 P12 C19 C115 . . . . -52.8(2) Y NI11 P12 C19 C115 . . . . 83.3(2) Y O12 P12 C19 C116 . . . . 73.8(2) Y C110 P12 C19 C116 . . . . -178.2(2) Y NI11 P12 C19 C116 . . . . -42.2(3) Y O12 P12 C110 C118 . . . . 53.6(2) Y C19 P12 C110 C118 . . . . -52.6(2) Y NI11 P12 C110 C118 . . . . 170.95(17) Y O12 P12 C110 C117 . . . . -70.8(2) Y C19 P12 C110 C117 . . . . -177.1(2) Y NI11 P12 C110 C117 . . . . 46.5(2) Y C22 NI21 P21 O21 . . . . 0.34(11) Y P22 NI21 P21 O21 . . . . -13.61(17) Y BR21 NI21 P21 O21 . . . . 178.20(8) Y C22 NI21 P21 C28 . . . . 114.58(14) Y P22 NI21 P21 C28 . . . . 100.62(17) Y BR21 NI21 P21 C28 . . . . -67.57(11) Y C22 NI21 P21 C27 . . . . -113.17(14) Y P22 NI21 P21 C27 . . . . -127.13(17) Y BR21 NI21 P21 C27 . . . . 64.69(12) Y C22 NI21 P22 O22 . . . . 3.91(11) Y P21 NI21 P22 O22 . . . . 17.87(17) Y BR21 NI21 P22 O22 . . . . -173.95(8) Y C22 NI21 P22 C29 . . . . 118.03(13) Y P21 NI21 P22 C29 . . . . 131.99(16) Y BR21 NI21 P22 C29 . . . . -59.83(11) Y C22 NI21 P22 C210 . . . . -109.50(14) Y P21 NI21 P22 C210 . . . . -95.54(17) Y BR21 NI21 P22 C210 . . . . 72.64(12) Y C28 P21 O21 C21 . . . . -124.01(19) Y C27 P21 O21 C21 . . . . 125.88(19) Y NI21 P21 O21 C21 . . . . -2.18(19) Y C29 P22 O22 C23 . . . . -128.03(19) Y C210 P22 O22 C23 . . . . 121.7(2) Y NI21 P22 O22 C23 . . . . -3.1(2) Y P21 O21 C21 C26 . . . . -175.7(2) Y P21 O21 C21 C22 . . . . 3.6(3) Y C26 C21 C22 C23 . . . . -1.9(4) Y O21 C21 C22 C23 . . . . 178.8(2) Y C26 C21 C22 NI21 . . . . 175.7(2) Y O21 C21 C22 NI21 . . . . -3.7(4) Y P21 NI21 C22 C21 . . . . 1.7(2) Y P22 NI21 C22 C21 . . . . 177.9(2) Y P21 NI21 C22 C23 . . . . 179.1(2) Y P22 NI21 C22 C23 . . . . -4.7(2) Y O21 C21 C26 C25 . . . . -179.3(2) Y C22 C21 C26 C25 . . . . 1.4(4) Y C21 C26 C25 C24 . . . . 0.3(4) Y C26 C25 C24 C23 . . . . -1.3(4) Y P22 O22 C23 C24 . . . . -179.3(2) Y P22 O22 C23 C22 . . . . 0.0(3) Y C25 C24 C23 O22 . . . . 180.0(3) Y C25 C24 C23 C22 . . . . 0.7(4) Y C21 C22 C23 O22 . . . . -178.5(2) Y NI21 C22 C23 O22 . . . . 4.0(4) Y C21 C22 C23 C24 . . . . 0.8(4) Y NI21 C22 C23 C24 . . . . -176.8(2) Y O21 P21 C27 C212 . . . . 160.9(2) Y C28 P21 C27 C212 . . . . 53.0(2) Y NI21 P21 C27 C212 . . . . -82.7(2) Y O21 P21 C27 C211 . . . . -74.5(2) Y C28 P21 C27 C211 . . . . 177.6(2) Y NI21 P21 C27 C211 . . . . 42.0(3) Y O21 P21 C28 C213 . . . . -45.4(2) Y C27 P21 C28 C213 . . . . 59.9(3) Y NI21 P21 C28 C213 . . . . -160.9(2) Y O21 P21 C28 C214 . . . . 81.2(2) Y C27 P21 C28 C214 . . . . -173.5(2) Y NI21 P21 C28 C214 . . . . -34.3(2) Y O22 P22 C29 C216 . . . . -49.9(2) Y C210 P22 C29 C216 . . . . 56.5(2) Y NI21 P22 C29 C216 . . . . -166.00(17) Y O22 P22 C29 C215 . . . . 74.3(2) Y C210 P22 C29 C215 . . . . -179.4(2) Y NI21 P22 C29 C215 . . . . -41.9(2) Y O22 P22 C210 C218 . . . . 162.1(2) Y C29 P22 C210 C218 . . . . 55.3(2) Y NI21 P22 C210 C218 . . . . -82.2(2) Y O22 P22 C210 C217 . . . . -73.6(2) Y C29 P22 C210 C217 . . . . 179.6(2) Y NI21 P22 C210 C217 . . . . 42.1(2) Y _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 72.99 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.703 _refine_diff_density_min -0.491 _refine_diff_density_rms 0.101 # Attachment 'valer10.cif' data_valer10 _database_code_depnum_ccdc_archive 'CCDC 620343' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H33 Br2 Ni O2 P2' _chemical_formula_sum 'C15 H33 Br2 Ni O2 P2' _chemical_formula_weight 525.88 _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' Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 '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 34.4889(8) _cell_length_b 7.0423(2) _cell_length_c 22.1302(5) _cell_angle_alpha 90.00 _cell_angle_beta 127.664(1) _cell_angle_gamma 90.00 _cell_volume 4254.90(18) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 16037 _cell_measurement_theta_min 3.24 _cell_measurement_theta_max 68.90 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2136 _exptl_absorpt_coefficient_mu 7.163 _exptl_absorpt_correction_Type multi-scan _exptl_absorpt_correction_T_min 0.660 _exptl_absorpt_correction_T_max 0.810 _exptl_absorpt_process_details 'Sadabs (Sheldrick,1996)' _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 Platform diffractometer, equipped with a Bruker SMART 2K Charged-Coupled Device (CCD) Area Detector using the program SMART and normal focus sealed tube source graphite monochromated Cu-K\a radiation. The crystal-to-detector distance was 4.908 cm, and the data collection was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 9.0 degree scan in 30 frames over four different parts of the reciprocal space (120 frames total). One complete sphere of data was collected, to better than 0.8\%A resolution. Upon completion of the data collection, the first 101 frames were recollected in order to improve the decay correction analysis. ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart 2000' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.5 _diffrn_standards_number 181 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.59 _diffrn_reflns_number 29028 _diffrn_reflns_av_R_equivalents 0.026 _diffrn_reflns_av_sigmaI/netI 0.0149 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 69.04 _reflns_number_total 3930 _reflns_number_gt 3610 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1999)' _computing_cell_refinement 'SMART (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'UdMX (local program)' _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^)+(0.1050P)^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 3930 _refine_ls_number_parameters 207 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1758 _refine_ls_wR_factor_gt 0.1735 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.083 _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 0.11848(3) 0.19621(11) 0.02187(4) 0.0193(2) Uani 1 1 d . . . Br1 Br 0.17935(2) 0.43549(10) 0.08372(4) 0.0418(2) Uani 1 1 d . . . Br2 Br 0.04041(2) 0.36112(10) -0.06150(4) 0.0446(2) Uani 1 1 d . . . P1 P 0.12959(5) 0.14200(18) -0.06610(7) 0.0239(3) Uani 1 1 d . . . P2 P 0.10892(4) 0.14312(16) 0.11239(7) 0.0197(3) Uani 1 1 d . . . O1 O 0.10221(14) -0.0560(5) -0.1068(2) 0.0313(8) Uani 1 1 d . . . O2 O 0.07516(13) -0.0464(5) 0.0838(2) 0.0253(7) Uani 1 1 d . . . C1 C 0.0683(2) -0.1102(8) -0.0914(3) 0.0308(11) Uani 1 1 d . . . H1A H 0.0607 -0.2473 -0.1020 0.037 Uiso 1 1 calc R . . H1B H 0.0374 -0.0381 -0.1252 0.037 Uiso 1 1 calc R . . C2 C 0.09129(18) -0.0689(7) -0.0084(3) 0.0251(10) Uani 1 1 d . . . H2 H 0.1190 -0.1597 0.0240 0.030 Uiso 1 1 calc R . . C3 C 0.05433(18) -0.1015(7) 0.0066(3) 0.0261(10) Uani 1 1 d . . . H3A H 0.0244 -0.0260 -0.0298 0.031 Uiso 1 1 calc R . . H3B H 0.0450 -0.2373 -0.0010 0.031 Uiso 1 1 calc R . . C4 C 0.1928(2) 0.0933(8) -0.0284(3) 0.0324(12) Uani 1 1 d . . . H4 H 0.2111 0.2163 -0.0096 0.039 Uiso 1 1 calc R . . C5 C 0.1026(3) 0.3158(10) -0.1432(4) 0.0477(16) Uani 1 1 d . . . H5 H 0.0754 0.3683 -0.1438 0.057 Uiso 1 1 calc R . . C6 C 0.16178(18) 0.0667(8) 0.2076(3) 0.0271(11) Uani 1 1 d . . . H6 H 0.1486 0.0009 0.2317 0.033 Uiso 1 1 calc R . . C7 C 0.07347(18) 0.3136(7) 0.1230(3) 0.0256(10) Uani 1 1 d . . . H7 H 0.0409 0.3217 0.0715 0.031 Uiso 1 1 calc R . . C8 C 0.2167(2) -0.0400(11) 0.0394(4) 0.0485(16) Uani 1 1 d . . . H8A H 0.1976 -0.1576 0.0239 0.073 Uiso 1 1 calc R . . H8B H 0.2178 0.0209 0.0803 0.073 Uiso 1 1 calc R . . H8C H 0.2501 -0.0695 0.0579 0.073 Uiso 1 1 calc R . . C9 C 0.1972(3) 0.0149(12) -0.0887(4) 0.0511(17) Uani 1 1 d . . . H9A H 0.2319 -0.0055 -0.0655 0.077 Uiso 1 1 calc R . . H9B H 0.1831 0.1061 -0.1307 0.077 Uiso 1 1 calc R . . H9C H 0.1796 -0.1059 -0.1084 0.077 Uiso 1 1 calc R . . C10 C 0.1344(3) 0.4877(11) -0.1213(4) 0.060(2) Uani 1 1 d U . . H10A H 0.1632 0.4535 -0.1179 0.091 Uiso 1 1 calc R . . H10B H 0.1449 0.5351 -0.0717 0.091 Uiso 1 1 calc R . . H10C H 0.1158 0.5868 -0.1600 0.091 Uiso 1 1 calc R . . C11 C 0.0757(4) 0.2408(15) -0.2208(5) 0.084(3) Uani 1 1 d U . . H11A H 0.0545 0.3401 -0.2576 0.126 Uiso 1 1 calc R . . H11B H 0.0557 0.1325 -0.2271 0.126 Uiso 1 1 calc R . . H11C H 0.0990 0.1995 -0.2297 0.126 Uiso 1 1 calc R . . C12 C 0.1920(2) -0.0789(10) 0.2016(3) 0.0420(14) Uani 1 1 d . . . H12A H 0.2090 -0.0160 0.1843 0.063 Uiso 1 1 calc R . . H12B H 0.1703 -0.1777 0.1649 0.063 Uiso 1 1 calc R . . H12C H 0.2161 -0.1367 0.2517 0.063 Uiso 1 1 calc R . . C13 C 0.1941(2) 0.2300(10) 0.2609(3) 0.0384(13) Uani 1 1 d . . . H13A H 0.2230 0.1781 0.3088 0.058 Uiso 1 1 calc R . . H13B H 0.1755 0.3085 0.2716 0.058 Uiso 1 1 calc R . . H13C H 0.2045 0.3078 0.2363 0.058 Uiso 1 1 calc R . . C14 C 0.0942(2) 0.5161(8) 0.1413(4) 0.0362(12) Uani 1 1 d U . . H14A H 0.0712 0.6025 0.1396 0.054 Uiso 1 1 calc R . . H14B H 0.0988 0.5562 0.1037 0.054 Uiso 1 1 calc R . . H14C H 0.1257 0.5189 0.1925 0.054 Uiso 1 1 calc R . . C15 C 0.0628(2) 0.2411(9) 0.1758(3) 0.0326(12) Uani 1 1 d U . . H15A H 0.0931 0.2403 0.2284 0.049 Uiso 1 1 calc R . . H15B H 0.0497 0.1118 0.1609 0.049 Uiso 1 1 calc R . . H15C H 0.0388 0.3242 0.1724 0.049 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 0.0178(4) 0.0185(4) 0.0193(4) -0.0015(3) 0.0102(4) -0.0027(3) Br1 0.0403(4) 0.0434(4) 0.0410(4) -0.0116(3) 0.0243(3) -0.0165(3) Br2 0.0407(4) 0.0459(4) 0.0403(4) 0.0050(3) 0.0213(3) 0.0087(3) P1 0.0270(6) 0.0229(6) 0.0232(6) -0.0018(5) 0.0159(6) -0.0039(5) P2 0.0172(6) 0.0198(6) 0.0193(6) -0.0006(4) 0.0097(5) -0.0017(4) O1 0.037(2) 0.032(2) 0.0317(19) -0.0138(16) 0.0241(17) -0.0137(16) O2 0.0274(18) 0.0238(18) 0.0269(17) -0.0033(14) 0.0178(15) -0.0070(14) C1 0.035(3) 0.029(3) 0.032(3) -0.010(2) 0.022(2) -0.013(2) C2 0.025(2) 0.024(2) 0.027(2) -0.0029(19) 0.016(2) -0.0045(19) C3 0.025(2) 0.025(2) 0.027(2) -0.007(2) 0.015(2) -0.008(2) C4 0.033(3) 0.034(3) 0.040(3) -0.008(2) 0.028(3) -0.005(2) C5 0.056(4) 0.048(4) 0.032(3) 0.011(3) 0.023(3) 0.000(3) C6 0.022(2) 0.033(3) 0.022(2) 0.005(2) 0.012(2) 0.001(2) C7 0.019(2) 0.028(3) 0.027(2) -0.002(2) 0.013(2) 0.0003(19) C8 0.040(3) 0.057(4) 0.051(4) 0.011(3) 0.029(3) 0.014(3) C9 0.052(4) 0.066(5) 0.054(4) -0.019(4) 0.042(4) -0.008(3) C10 0.085(5) 0.040(3) 0.045(4) 0.008(3) 0.034(4) -0.008(4) C11 0.098(6) 0.072(5) 0.052(4) 0.012(4) 0.031(4) -0.013(5) C12 0.032(3) 0.048(4) 0.033(3) 0.006(3) 0.013(3) 0.013(3) C13 0.026(3) 0.047(3) 0.026(3) -0.002(2) 0.008(2) -0.006(2) C14 0.041(3) 0.026(3) 0.044(3) -0.004(2) 0.028(3) 0.001(2) C15 0.031(3) 0.040(3) 0.033(3) -0.005(2) 0.022(2) -0.003(2) _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 Ni1 C2 . . 2.011(5) Y Ni1 P1 . . 2.2348(14) Y Ni1 P2 . . 2.2514(14) Y Ni1 Br1 . . 2.3683(9) Y Ni1 Br2 . . 2.4355(10) Y P1 O1 . . 1.615(4) Y P1 C5 . . 1.825(6) Y P1 C4 . . 1.829(6) Y P2 O2 . . 1.624(3) Y P2 C7 . . 1.828(5) Y P2 C6 . . 1.833(5) Y O1 C1 . . 1.454(6) Y O2 C3 . . 1.444(6) Y C1 C2 . . 1.519(7) Y C1 H1a . . 0.99 ? C1 H1b . . 0.99 ? C2 C3 . . 1.519(7) Y C2 H2 . . 1 ? C3 H3a . . 0.99 ? C3 H3b . . 0.99 ? C4 C8 . . 1.517(9) Y C4 C9 . . 1.536(8) Y C4 H4 . . 1 ? C5 C11 . . 1.464(11) Y C5 C10 . . 1.502(10) Y C5 H5 . . 1 ? C6 C12 . . 1.525(8) Y C6 C13 . . 1.532(8) Y C6 H6 . . 1 ? C7 C15 . . 1.513(7) Y C7 C14 . . 1.534(7) Y C7 H7 . . 1 ? C8 H8a . . 0.98 ? C8 H8b . . 0.98 ? C8 H8c . . 0.98 ? C9 H9a . . 0.98 ? C9 H9b . . 0.98 ? C9 H9c . . 0.98 ? C10 H10a . . 0.98 ? C10 H10b . . 0.98 ? C10 H10c . . 0.98 ? C11 H11a . . 0.98 ? C11 H11b . . 0.98 ? C11 H11c . . 0.98 ? C12 H12a . . 0.98 ? C12 H12b . . 0.98 ? C12 H12c . . 0.98 ? C13 H13a . . 0.98 ? C13 H13b . . 0.98 ? C13 H13c . . 0.98 ? C14 H14a . . 0.98 ? C14 H14b . . 0.98 ? C14 H14c . . 0.98 ? C15 H15a . . 0.98 ? C15 H15b . . 0.98 ? C15 H15c . . 0.98 ? 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 NI1 P1 . . . 81.04(15) Y C2 NI1 P2 . . . 81.40(15) Y P1 NI1 P2 . . . 160.57(6) Y C2 NI1 BR1 . . . 157.09(15) Y P1 NI1 BR1 . . . 93.54(4) Y P2 NI1 BR1 . . . 99.43(4) Y C2 NI1 BR2 . . . 96.64(15) Y P1 NI1 BR2 . . . 96.91(5) Y P2 NI1 BR2 . . . 93.33(4) Y BR1 NI1 BR2 . . . 106.13(4) Y O1 P1 C5 . . . 105.5(3) Y O1 P1 C4 . . . 102.7(2) Y C5 P1 C4 . . . 109.7(3) Y O1 P1 NI1 . . . 106.30(14) Y C5 P1 NI1 . . . 116.0(3) Y C4 P1 NI1 . . . 115.21(19) Y O2 P2 C7 . . . 102.3(2) Y O2 P2 C6 . . . 100.3(2) Y C7 P2 C6 . . . 108.6(2) Y O2 P2 NI1 . . . 104.47(13) Y C7 P2 NI1 . . . 118.55(17) Y C6 P2 NI1 . . . 119.22(17) Y C1 O1 P1 . . . 112.1(3) Y C3 O2 P2 . . . 113.7(3) Y O1 C1 C2 . . . 109.5(4) Y O1 C1 H1A . . . 109.8 ? C2 C1 H1A . . . 109.8 ? O1 C1 H1B . . . 109.8 ? C2 C1 H1B . . . 109.8 ? H1A C1 H1B . . . 108.2 ? C3 C2 C1 . . . 110.4(4) Y C3 C2 NI1 . . . 110.5(3) Y C1 C2 NI1 . . . 111.9(3) Y C3 C2 H2 . . . 107.9 ? C1 C2 H2 . . . 107.9 ? NI1 C2 H2 . . . 107.9 ? O2 C3 C2 . . . 109.9(4) Y O2 C3 H3A . . . 109.7 ? C2 C3 H3A . . . 109.7 ? O2 C3 H3B . . . 109.7 ? C2 C3 H3B . . . 109.7 ? H3A C3 H3B . . . 108.2 ? C8 C4 C9 . . . 110.8(6) Y C8 C4 P1 . . . 110.0(4) Y C9 C4 P1 . . . 113.3(4) Y C8 C4 H4 . . . 107.5 ? C9 C4 H4 . . . 107.5 ? P1 C4 H4 . . . 107.5 ? C11 C5 C10 . . . 118.9(7) Y C11 C5 P1 . . . 116.8(6) Y C10 C5 P1 . . . 112.6(5) Y C11 C5 H5 . . . 101.6 ? C10 C5 H5 . . . 101.6 ? P1 C5 H5 . . . 101.6 ? C12 C6 C13 . . . 110.9(5) Y C12 C6 P2 . . . 110.5(4) Y C13 C6 P2 . . . 114.2(4) Y C12 C6 H6 . . . 107 ? C13 C6 H6 . . . 107 ? P2 C6 H6 . . . 107 ? C15 C7 C14 . . . 113.7(5) Y C15 C7 P2 . . . 112.0(4) Y C14 C7 P2 . . . 113.9(4) Y C15 C7 H7 . . . 105.4 ? C14 C7 H7 . . . 105.4 ? P2 C7 H7 . . . 105.4 ? C4 C8 H8A . . . 109.5 ? C4 C8 H8B . . . 109.5 ? H8A C8 H8B . . . 109.5 ? C4 C8 H8C . . . 109.5 ? H8A C8 H8C . . . 109.5 ? H8B C8 H8C . . . 109.5 ? C4 C9 H9A . . . 109.5 ? C4 C9 H9B . . . 109.5 ? H9A C9 H9B . . . 109.5 ? C4 C9 H9C . . . 109.5 ? H9A C9 H9C . . . 109.5 ? H9B C9 H9C . . . 109.5 ? C5 C10 H10A . . . 109.5 ? C5 C10 H10B . . . 109.5 ? H10A C10 H10B . . . 109.5 ? C5 C10 H10C . . . 109.5 ? H10A C10 H10C . . . 109.5 ? H10B C10 H10C . . . 109.5 ? C5 C11 H11A . . . 109.5 ? C5 C11 H11B . . . 109.5 ? H11A C11 H11B . . . 109.5 ? C5 C11 H11C . . . 109.5 ? H11A C11 H11C . . . 109.5 ? H11B C11 H11C . . . 109.5 ? C6 C12 H12A . . . 109.5 ? C6 C12 H12B . . . 109.5 ? H12A C12 H12B . . . 109.5 ? C6 C12 H12C . . . 109.5 ? H12A C12 H12C . . . 109.5 ? H12B C12 H12C . . . 109.5 ? C6 C13 H13A . . . 109.5 ? C6 C13 H13B . . . 109.5 ? H13A C13 H13B . . . 109.5 ? C6 C13 H13C . . . 109.5 ? H13A C13 H13C . . . 109.5 ? H13B C13 H13C . . . 109.5 ? C7 C14 H14A . . . 109.5 ? C7 C14 H14B . . . 109.5 ? H14A C14 H14B . . . 109.5 ? C7 C14 H14C . . . 109.5 ? H14A C14 H14C . . . 109.5 ? H14B C14 H14C . . . 109.5 ? C7 C15 H15A . . . 109.5 ? C7 C15 H15B . . . 109.5 ? H15A C15 H15B . . . 109.5 ? C7 C15 H15C . . . 109.5 ? H15A C15 H15C . . . 109.5 ? H15B C15 H15C . . . 109.5 ? 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 C2 NI1 P1 O1 . . . . 8.3(2) Y P2 NI1 P1 O1 . . . . 33.9(2) Y BR1 NI1 P1 O1 . . . . 165.90(16) Y BR2 NI1 P1 O1 . . . . -87.37(16) Y C2 NI1 P1 C5 . . . . 125.1(3) Y P2 NI1 P1 C5 . . . . 150.7(3) Y BR1 NI1 P1 C5 . . . . -77.3(3) Y BR2 NI1 P1 C5 . . . . 29.5(3) Y C2 NI1 P1 C4 . . . . -104.7(3) Y P2 NI1 P1 C4 . . . . -79.1(3) Y BR1 NI1 P1 C4 . . . . 52.9(2) Y BR2 NI1 P1 C4 . . . . 159.6(2) Y C2 NI1 P2 O2 . . . . -13.1(2) Y P1 NI1 P2 O2 . . . . -38.7(2) Y BR1 NI1 P2 O2 . . . . -169.89(14) Y BR2 NI1 P2 O2 . . . . 83.14(14) Y C2 NI1 P2 C7 . . . . -126.1(2) Y P1 NI1 P2 C7 . . . . -151.7(2) Y BR1 NI1 P2 C7 . . . . 77.09(19) Y BR2 NI1 P2 C7 . . . . -29.87(19) Y C2 NI1 P2 C6 . . . . 97.8(3) Y P1 NI1 P2 C6 . . . . 72.2(3) Y BR1 NI1 P2 C6 . . . . -59.0(2) Y BR2 NI1 P2 C6 . . . . -166.0(2) Y C5 P1 O1 C1 . . . . -107.6(4) Y C4 P1 O1 C1 . . . . 137.4(4) Y NI1 P1 O1 C1 . . . . 16.0(4) Y C7 P2 O2 C3 . . . . 113.3(4) Y C6 P2 O2 C3 . . . . -134.9(3) Y NI1 P2 O2 C3 . . . . -10.8(3) Y P1 O1 C1 C2 . . . . -40.9(5) Y O1 C1 C2 C3 . . . . 173.0(4) Y O1 C1 C2 NI1 . . . . 49.5(5) Y P1 NI1 C2 C3 . . . . -154.2(4) Y P2 NI1 C2 C3 . . . . 34.1(3) Y BR1 NI1 C2 C3 . . . . 128.0(4) Y BR2 NI1 C2 C3 . . . . -58.2(3) Y P1 NI1 C2 C1 . . . . -30.7(3) Y P2 NI1 C2 C1 . . . . 157.7(4) Y BR1 NI1 C2 C1 . . . . -108.4(5) Y BR2 NI1 C2 C1 . . . . 65.3(4) Y P2 O2 C3 C2 . . . . 38.5(5) Y C1 C2 C3 O2 . . . . -175.1(4) Y NI1 C2 C3 O2 . . . . -50.8(5) Y O1 P1 C4 C8 . . . . -72.3(5) Y C5 P1 C4 C8 . . . . 175.9(5) Y NI1 P1 C4 C8 . . . . 42.8(5) Y O1 P1 C4 C9 . . . . 52.3(5) Y C5 P1 C4 C9 . . . . -59.5(6) Y NI1 P1 C4 C9 . . . . 167.4(4) Y O1 P1 C5 C11 . . . . -17.3(8) Y C4 P1 C5 C11 . . . . 92.7(8) Y NI1 P1 C5 C11 . . . . -134.6(7) Y O1 P1 C5 C10 . . . . -160.0(6) Y C4 P1 C5 C10 . . . . -50.0(7) Y NI1 P1 C5 C10 . . . . 82.7(6) Y O2 P2 C6 C12 . . . . 72.1(4) Y C7 P2 C6 C12 . . . . 178.9(4) Y NI1 P2 C6 C12 . . . . -41.1(5) Y O2 P2 C6 C13 . . . . -162.1(4) Y C7 P2 C6 C13 . . . . -55.2(5) Y NI1 P2 C6 C13 . . . . 84.8(4) Y O2 P2 C7 C15 . . . . 55.7(4) Y C6 P2 C7 C15 . . . . -49.8(4) Y NI1 P2 C7 C15 . . . . 169.9(3) Y O2 P2 C7 C14 . . . . -173.5(4) Y C6 P2 C7 C14 . . . . 81.0(4) Y NI1 P2 C7 C14 . . . . -59.3(4) Y _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 69.04 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.641 _refine_diff_density_min -1.423 _refine_diff_density_rms 0.161