# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 182/1464 # CIF file data_global #============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author # Name and address of author for corresponding ; Philip Coppens Department of Chemistry State University of New York at Buffalo Buffalo, NY 14260-3000 USA ; _publ_contact_author_phone '+1 (716) 645-6800 ext 2217' _publ_contact_author_fax '+1 (716) 645-6948' _publ_contact_author_email 'coppens@acsu.buffalo.edu' _publ_contact_letter ; ; _publ_requested_journal 'Chemical Communications' _publ_section_title ; ; _publ_section_abstract ; ; #============================================================================== # 3. TITLE AND AUTHOR LIST loop_ _publ_author_name _publ_author_address 'Yuegang Zhang and Philip Coppens' ; Department of Chemistry Natural Sciences Complex State University of New York at Buffalo Buffalo, NY 14260-3000 USA ; #============================================================================== # data data_tppopanb _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; triphenylphosphine oxide p-amino-p'-nitrobiphenyl ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H25 N2 O3 P' _chemical_formula_weight 492.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2719(8) _cell_length_b 10.4330(10) _cell_length_c 14.4569(11) _cell_angle_alpha 106.122(4) _cell_angle_beta 107.714(5) _cell_angle_gamma 94.691(4) _cell_volume 1258.47(19) _cell_formula_units_Z 2 _cell_measurement_temperature 90(1) _cell_measurement_reflns_used 800 _cell_measurement_theta_min 2.07 _cell_measurement_theta_max 52.27 _exptl_crystal_description plate _exptl_crystal_colour 'orange red' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.144 _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 90(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART CCD 1K' _diffrn_measurement_method 'oscillation around \w axis' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 89125 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0644 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 52.27 _reflns_number_total 27997 _reflns_number_gt 16028 _reflns_threshold_expression >4sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXP-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^ > 4sigma(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^)+(0.0344P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0239(14) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 13140 _refine_ls_number_parameters 426 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0497 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0873 _refine_ls_wR_factor_gt 0.0837 _refine_ls_goodness_of_fit_ref 0.865 _refine_ls_restrained_S_all 0.865 _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 1.18021(8) 0.06195(8) 0.89328(6) 0.02033(13) Uani 1 1 d . . . C2 C 1.13859(8) 0.03375(8) 0.78685(6) 0.01966(13) Uani 1 1 d . . . C3 C 0.99789(8) 0.05473(8) 0.72942(6) 0.01890(13) Uani 1 1 d . . . C4 C 0.89286(8) 0.10690(8) 0.77588(6) 0.01797(12) Uani 1 1 d . . . C5 C 0.93678(9) 0.13807(9) 0.88270(6) 0.02065(13) Uani 1 1 d . . . C6 C 1.07682(9) 0.11690(9) 0.94060(6) 0.02177(14) Uani 1 1 d . . . C7 C 0.74191(8) 0.12679(8) 0.71453(6) 0.01876(13) Uani 1 1 d . . . C8 C 0.72306(10) 0.15718(9) 0.62330(7) 0.02303(14) Uani 1 1 d . . . C9 C 0.58136(10) 0.17412(9) 0.56397(7) 0.02547(16) Uani 1 1 d . . . C10 C 0.45675(9) 0.16085(9) 0.59701(7) 0.02470(16) Uani 1 1 d . . . C11 C 0.47045(9) 0.13212(10) 0.68699(8) 0.02715(17) Uani 1 1 d . . . C12 C 0.61273(9) 0.11443(9) 0.74522(7) 0.02348(15) Uani 1 1 d . . . N1 N 1.31794(8) 0.03711(9) 0.94817(7) 0.03006(17) Uani 1 1 d . . . N2 N 0.30543(10) 0.17452(9) 0.53390(7) 0.03265(18) Uani 1 1 d . . . O1 O 0.29409(10) 0.20090(8) 0.45465(6) 0.04155(19) Uani 1 1 d . . . O2 O 0.19539(9) 0.15763(11) 0.56309(8) 0.0522(2) Uani 1 1 d . . . C13 C 0.66768(7) 0.34462(7) 0.35491(5) 0.01459(11) Uani 1 1 d . . . C14 C 0.79953(8) 0.28622(8) 0.37885(6) 0.01975(13) Uani 1 1 d . . . C15 C 0.90252(8) 0.32558(9) 0.47871(6) 0.02192(14) Uani 1 1 d . . . C16 C 0.87539(8) 0.42465(9) 0.55518(6) 0.02070(14) Uani 1 1 d . . . C17 C 0.74599(9) 0.48482(9) 0.53233(6) 0.02122(14) Uani 1 1 d . . . C18 C 0.64159(8) 0.44469(8) 0.43233(6) 0.01813(12) Uani 1 1 d . . . C19 C 0.62685(7) 0.39140(7) 0.16284(6) 0.01500(11) Uani 1 1 d . . . C20 C 0.70430(8) 0.52525(8) 0.21606(6) 0.01971(13) Uani 1 1 d . . . C21 C 0.76362(10) 0.60116(9) 0.16586(8) 0.02472(15) Uani 1 1 d . . . C22 C 0.74741(10) 0.54373(10) 0.06343(7) 0.02533(16) Uani 1 1 d . . . C23 C 0.67184(10) 0.41075(9) 0.01044(7) 0.02321(15) Uani 1 1 d . . . C24 C 0.61064(8) 0.33441(8) 0.05951(6) 0.01820(12) Uani 1 1 d . . . C25 C 0.35852(7) 0.33406(7) 0.21734(5) 0.01414(11) Uani 1 1 d . . . C26 C 0.25162(8) 0.24038(8) 0.22729(6) 0.01820(12) Uani 1 1 d . . . C27 C 0.10145(8) 0.26243(9) 0.21400(7) 0.02166(14) Uani 1 1 d . . . C28 C 0.05704(8) 0.37711(9) 0.19048(6) 0.02159(14) Uani 1 1 d . . . C29 C 0.16380(8) 0.47289(9) 0.18369(7) 0.02256(15) Uani 1 1 d . . . C30 C 0.31460(8) 0.45176(8) 0.19742(6) 0.01899(13) Uani 1 1 d . . . P1 P 0.544193(19) 0.289329(19) 0.222868(14) 0.01309(4) Uani 1 1 d . . . O3 O 0.52924(6) 0.14016(6) 0.17206(4) 0.01785(10) Uani 1 1 d . . . H1A H 1.3429(15) 0.0513(14) 1.0146(11) 0.038(3) Uiso 1 1 d . . . H1B H 1.3677(16) -0.0180(14) 0.9139(11) 0.044(4) Uiso 1 1 d . . . H2 H 1.2078(13) -0.0044(12) 0.7537(9) 0.025(3) Uiso 1 1 d . . . H3 H 0.9748(12) 0.0318(11) 0.6576(9) 0.020(3) Uiso 1 1 d . . . H5 H 0.8694(13) 0.1764(12) 0.9178(9) 0.026(3) Uiso 1 1 d . . . H6 H 1.1019(14) 0.1398(12) 1.0112(10) 0.030(3) Uiso 1 1 d . . . H8 H 0.8119(14) 0.1679(12) 0.6038(9) 0.030(3) Uiso 1 1 d . . . H9 H 0.5679(13) 0.1933(12) 0.5012(9) 0.025(3) Uiso 1 1 d . . . H11 H 0.3801(15) 0.1184(14) 0.7050(10) 0.040(4) Uiso 1 1 d . . . H12 H 0.6190(14) 0.0919(13) 0.8081(10) 0.035(3) Uiso 1 1 d . . . H14 H 0.8189(13) 0.2199(12) 0.3241(9) 0.027(3) Uiso 1 1 d . . . H15 H 0.9895(14) 0.2824(13) 0.4941(9) 0.031(3) Uiso 1 1 d . . . H16 H 0.9447(13) 0.4535(12) 0.6236(9) 0.027(3) Uiso 1 1 d . . . H17 H 0.7287(14) 0.5561(13) 0.5853(10) 0.035(3) Uiso 1 1 d . . . H18 H 0.5516(13) 0.4858(12) 0.4175(9) 0.025(3) Uiso 1 1 d . . . H20 H 0.7192(13) 0.5653(12) 0.2858(9) 0.022(3) Uiso 1 1 d . . . H21 H 0.8157(14) 0.6900(13) 0.2019(10) 0.035(3) Uiso 1 1 d . . . H22 H 0.7889(15) 0.5978(13) 0.0303(10) 0.036(3) Uiso 1 1 d . . . H23 H 0.6598(13) 0.3724(12) -0.0615(9) 0.026(3) Uiso 1 1 d . . . H24 H 0.5571(13) 0.2424(13) 0.0219(9) 0.029(3) Uiso 1 1 d . . . H26 H 0.2838(13) 0.1590(12) 0.2446(9) 0.026(3) Uiso 1 1 d . . . H27 H 0.0278(14) 0.1964(13) 0.2196(10) 0.033(3) Uiso 1 1 d . . . H28 H -0.0428(14) 0.3897(13) 0.1816(9) 0.033(3) Uiso 1 1 d . . . H29 H 0.1328(14) 0.5560(13) 0.1686(10) 0.033(3) Uiso 1 1 d . . . H30 H 0.3905(13) 0.5202(12) 0.1941(9) 0.027(3) Uiso 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 0.0165(2) 0.0146(3) 0.0229(3) -0.0002(3) 0.0029(2) 0.0015(2) C2 0.0176(3) 0.0150(3) 0.0233(3) 0.0017(3) 0.0074(2) 0.0007(2) C3 0.0192(3) 0.0159(3) 0.0201(3) 0.0041(3) 0.0070(2) -0.0003(2) C4 0.0173(2) 0.0160(3) 0.0203(3) 0.0062(3) 0.0058(2) 0.0018(2) C5 0.0199(3) 0.0211(3) 0.0207(3) 0.0052(3) 0.0073(2) 0.0062(3) C6 0.0212(3) 0.0215(4) 0.0183(3) 0.0019(3) 0.0042(2) 0.0059(3) C7 0.0188(3) 0.0161(3) 0.0212(3) 0.0077(3) 0.0052(2) 0.0023(2) C8 0.0251(3) 0.0218(4) 0.0239(4) 0.0115(3) 0.0073(3) 0.0026(3) C9 0.0310(4) 0.0210(4) 0.0232(4) 0.0109(3) 0.0040(3) 0.0047(3) C10 0.0239(3) 0.0190(4) 0.0266(4) 0.0082(3) 0.0008(3) 0.0061(3) C11 0.0207(3) 0.0314(4) 0.0332(4) 0.0162(4) 0.0084(3) 0.0090(3) C12 0.0203(3) 0.0284(4) 0.0267(4) 0.0152(3) 0.0084(3) 0.0071(3) N1 0.0214(3) 0.0327(4) 0.0237(3) -0.0031(3) -0.0001(2) 0.0112(3) N2 0.0303(3) 0.0254(4) 0.0339(4) 0.0089(3) -0.0017(3) 0.0113(3) O1 0.0457(4) 0.0352(4) 0.0332(4) 0.0143(3) -0.0055(3) 0.0120(3) O2 0.0281(3) 0.0745(7) 0.0583(6) 0.0311(5) 0.0079(3) 0.0241(4) C13 0.0139(2) 0.0154(3) 0.0146(3) 0.0046(2) 0.00522(19) 0.0032(2) C14 0.0165(2) 0.0201(3) 0.0207(3) 0.0036(3) 0.0056(2) 0.0062(2) C15 0.0162(2) 0.0242(4) 0.0236(4) 0.0079(3) 0.0034(2) 0.0063(3) C16 0.0168(2) 0.0263(4) 0.0165(3) 0.0070(3) 0.0026(2) 0.0019(3) C17 0.0199(3) 0.0252(4) 0.0152(3) 0.0022(3) 0.0051(2) 0.0046(3) C18 0.0172(2) 0.0209(3) 0.0154(3) 0.0036(3) 0.0054(2) 0.0067(2) C19 0.0136(2) 0.0152(3) 0.0173(3) 0.0057(2) 0.0065(2) 0.0024(2) C20 0.0194(3) 0.0160(3) 0.0232(3) 0.0044(3) 0.0089(2) 0.0004(2) C21 0.0235(3) 0.0182(4) 0.0341(4) 0.0103(3) 0.0113(3) -0.0002(3) C22 0.0246(3) 0.0264(4) 0.0328(4) 0.0179(4) 0.0132(3) 0.0039(3) C23 0.0259(3) 0.0276(4) 0.0217(4) 0.0133(3) 0.0108(3) 0.0057(3) C24 0.0193(3) 0.0194(3) 0.0169(3) 0.0072(3) 0.0068(2) 0.0024(2) C25 0.0128(2) 0.0158(3) 0.0132(3) 0.0039(2) 0.00466(18) 0.0009(2) C26 0.0180(2) 0.0158(3) 0.0207(3) 0.0033(3) 0.0095(2) -0.0001(2) C27 0.0164(2) 0.0223(4) 0.0234(4) 0.0012(3) 0.0099(2) -0.0027(3) C28 0.0133(2) 0.0307(4) 0.0185(3) 0.0044(3) 0.0056(2) 0.0030(3) C29 0.0175(3) 0.0303(4) 0.0253(4) 0.0145(3) 0.0085(2) 0.0092(3) C30 0.0154(2) 0.0229(3) 0.0236(3) 0.0129(3) 0.0082(2) 0.0052(2) P1 0.01348(6) 0.01259(8) 0.01304(8) 0.00324(6) 0.00528(5) 0.00157(5) O3 0.0217(2) 0.0131(2) 0.0181(2) 0.00280(19) 0.00803(18) 0.00224(18) _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 N1 1.3709(10) . yes C1 C2 1.4042(12) . yes C1 C6 1.4095(11) . yes C2 C3 1.3884(11) . yes C3 C4 1.4062(10) . yes C4 C5 1.4048(11) . yes C4 C7 1.4775(10) . yes C5 C6 1.3869(10) . yes C7 C8 1.4041(11) . yes C7 C12 1.4064(11) . yes C8 C9 1.3891(12) . yes C9 C10 1.3888(13) . yes C10 C11 1.3858(13) . yes C10 N2 1.4653(10) . yes C11 C12 1.3904(11) . yes N2 O1 1.2272(12) . yes N2 O2 1.2345(13) . yes C13 C18 1.3994(10) . yes C13 C14 1.4025(9) . yes C13 P1 1.7994(7) . yes C14 C15 1.3901(11) . yes C15 C16 1.3896(12) . yes C16 C17 1.3928(10) . yes C17 C18 1.3958(11) . yes C19 C20 1.4003(11) . yes C19 C24 1.4011(10) . yes C19 P1 1.8053(7) . yes C20 C21 1.3954(12) . yes C21 C22 1.3898(14) . yes C22 C23 1.3881(13) . yes C23 C24 1.3943(11) . yes C25 C30 1.4012(10) . yes C25 C26 1.4016(10) . yes C25 P1 1.8045(6) . yes C26 C27 1.3938(10) . yes C27 C28 1.3920(13) . yes C28 C29 1.3928(12) . yes C29 C30 1.3961(9) . yes P1 O3 1.4996(6) . yes 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 N1 C1 C2 120.25(7) . . yes N1 C1 C6 121.92(8) . . yes C2 C1 C6 117.83(7) . . yes C3 C2 C1 121.19(7) . . yes C2 C3 C4 121.24(7) . . yes C5 C4 C3 117.30(7) . . yes C5 C4 C7 121.46(7) . . yes C3 C4 C7 121.25(7) . . yes C6 C5 C4 121.83(7) . . yes C5 C6 C1 120.57(8) . . yes C8 C7 C12 118.13(7) . . yes C8 C7 C4 120.87(7) . . yes C12 C7 C4 121.00(7) . . yes C9 C8 C7 121.56(8) . . yes C10 C9 C8 118.44(8) . . yes C11 C10 C9 121.93(7) . . yes C11 C10 N2 118.88(8) . . yes C9 C10 N2 119.18(8) . . yes C10 C11 C12 119.00(8) . . yes C11 C12 C7 120.94(8) . . yes O1 N2 O2 123.39(8) . . yes O1 N2 C10 118.63(9) . . yes O2 N2 C10 117.97(9) . . yes C18 C13 C14 119.37(7) . . yes C18 C13 P1 123.59(5) . . yes C14 C13 P1 116.99(5) . . yes C15 C14 C13 120.54(7) . . yes C16 C15 C14 119.70(7) . . yes C15 C16 C17 120.42(7) . . yes C16 C17 C18 120.04(7) . . yes C17 C18 C13 119.92(6) . . yes C20 C19 C24 119.55(7) . . yes C20 C19 P1 121.98(6) . . yes C24 C19 P1 118.46(6) . . yes C21 C20 C19 119.94(8) . . yes C22 C21 C20 120.14(8) . . yes C23 C22 C21 120.21(8) . . yes C22 C23 C24 120.15(8) . . yes C23 C24 C19 120.00(8) . . yes C30 C25 C26 119.50(6) . . yes C30 C25 P1 123.33(5) . . yes C26 C25 P1 117.04(5) . . yes C27 C26 C25 119.99(7) . . yes C28 C27 C26 120.18(7) . . yes C27 C28 C29 120.20(6) . . yes C28 C29 C30 119.88(7) . . yes C29 C30 C25 120.17(7) . . yes O3 P1 C13 112.38(3) . . yes O3 P1 C25 111.01(3) . . yes C13 P1 C25 108.38(3) . . yes O3 P1 C19 112.58(3) . . yes C13 P1 C19 105.52(3) . . yes C25 P1 C19 106.63(3) . . yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O3 0.882(14) 2.280(14) 3.0552(10) 146.6(12) 1_656 N1 H1B O3 0.902(14) 2.030(15) 2.9310(10) 176.2(13) 2_756 C15 H15 O2 0.953(12) 2.511(12) 3.4470(11) 167.4(10) 1_655 _diffrn_measured_fraction_theta_max 0.452 _diffrn_reflns_theta_full 52.27 _diffrn_measured_fraction_theta_full 0.452 _refine_diff_density_max 0.497 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.058 #====END