# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Oleg Ozerov' _publ_contact_author_address ; Chemistry Brandeis University 415 Soouth Street, MS#015 Waltham Massachusetts 02454 UNITED STATES OF AMERICA ; _publ_contact_author_email OZEROV@BRANDEIS.EDU _publ_section_title ; Skeletal Change In The PNP Pincer Ligand Leads To A Highly Regioselective Alkyne Dimerization Catalyst ; _publ_author_name 'Oleg Ozerov' data_3a_cif _database_code_depnum_ccdc_archive 'CCDC 281662' _audit_creation_date 05-09-27 _audit_creation_method CRYSTALS_ver_12.80 _oxford_structure_analysis_title OZ023 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 10.3888(4) _cell_length_b 12.6906(13) _cell_length_c 20.1427(8) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2655.6(3) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source Rh -1.1178 0.9187 19.2957 0.7515 14.3501 8.2176 4.7343 25.8749 1.2892 98.6062 5.3280 'International Tables Vol C 4.2.6.8 and 6.1.1.4' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C26 H40 N1 P2 Rh1 # Dc = 1.33 Fooo = 1104.00 Mu = 7.76 M = 531.46 # Found Formula = C26 H38 N1 P2 Rh1 # Dc = 1.32 FOOO = 1104.00 Mu = 7.76 M = 529.45 _chemical_formula_sum 'C26 H40 N1 P2 Rh1' _chemical_formula_moiety 'C26 H40 N1 P2 Rh1' _chemical_compound_source ? _chemical_formula_weight 531.46 _cell_measurement_reflns_used 17 _cell_measurement_theta_min 12 _cell_measurement_theta_max 22 _cell_measurement_temperature 294 _exptl_crystal_description 'triangle column' _exptl_crystal_colour orange-red _exptl_crystal_size_min 0.29 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_max 0.50 _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.779 # Sheldrick geometric approximatio 0.76 0.80 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; Azimutal absorption correction (North et al., 1968) ; _exptl_absorpt_correction_T_min 0.73 _exptl_absorpt_correction_T_max 0.80 _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \\w _computing_data_collection 'CAD4 Express, (Straver, 1992)' _computing_data_reduction 'RC93 (Watkin, Prout & Lilley, 1994)' _computing_cell_refinement 'CAD4 Express, (Straver, 1992)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 3 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 294 _diffrn_reflns_number 4469 _reflns_number_total 4468 _diffrn_reflns_av_R_equivalents 0.043 # Number of reflections with Friedels Law is 4468 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4020 _diffrn_reflns_theta_min 2.534 _diffrn_reflns_theta_max 30.433 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.433 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 28 _reflns_limit_h_min 0 _reflns_limit_h_max 14 _reflns_limit_k_min 0 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 28 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.49 _refine_diff_density_max 0.84 _refine_ls_number_reflns 2818 _refine_ls_number_restraints 0 _refine_ls_number_parameters 271 #_refine_ls_R_factor_ref 0.0489 _refine_ls_wR_factor_ref 0.0505 _refine_ls_goodness_of_fit_ref 1.1480 #_reflns_number_all 4468 _refine_ls_R_factor_all 0.1069 _refine_ls_wR_factor_all 0.0951 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 2818 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_gt 0.0505 _refine_ls_shift/su_max 0.000451 _refine_ls_abs_structure_Flack 0.37(6) _refine_ls_abs_structure_details 'Flack, 0 Friedel-pairs' # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 2.03 0.234 1.77 ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Rh1 Rh 0.58367(4) 0.08694(4) 0.66211(2) 0.0363 1.0000 Uani . . . . . . P1 P 0.40399(15) 0.07513(14) 0.72364(7) 0.0358 1.0000 Uani . . . . . . P2 P 0.74089(14) 0.08320(15) 0.58584(7) 0.0356 1.0000 Uani . . . . . . C1 C 0.3778(6) -0.0679(4) 0.6218(3) 0.0327 1.0000 Uani . . . . . . C2 C 0.3307(6) -0.0374(6) 0.6850(3) 0.0404 1.0000 Uani . . . . . . C3 C 0.2356(7) -0.0960(7) 0.7191(3) 0.0540 1.0000 Uani . . . . . . C4 C 0.1823(8) -0.1843(7) 0.6904(5) 0.0634 1.0000 Uani . . . . . . C5 C 0.2194(7) -0.2118(6) 0.6291(5) 0.0572 1.0000 Uani . . . . . . C6 C 0.3169(7) -0.1590(5) 0.5941(4) 0.0447 1.0000 Uani . . . . . . C7 C 0.3425(9) -0.1952(6) 0.5243(5) 0.0623 1.0000 Uani . . . . . . C8 C 0.3333(9) -0.1030(8) 0.4766(4) 0.0654 1.0000 Uani . . . . . . C9 C 0.4599(7) -0.0492(6) 0.4720(3) 0.0446 1.0000 Uani . . . . . . C10 C 0.5154(8) -0.0420(6) 0.4098(4) 0.0506 1.0000 Uani . . . . . . C11 C 0.6361(9) -0.0016(7) 0.3985(4) 0.0548 1.0000 Uani . . . . . . C12 C 0.7037(7) 0.0335(6) 0.4525(3) 0.0463 1.0000 Uani . . . . . . C13 C 0.6545(6) 0.0291(5) 0.5169(3) 0.0379 1.0000 Uani . . . . . . C14 C 0.5294(6) -0.0141(5) 0.5291(3) 0.0345 1.0000 Uani . . . . . . C15 C 0.4106(8) 0.0488(7) 0.8134(3) 0.0527 1.0000 Uani . . . . . . C16 C 0.4613(11) 0.1469(9) 0.8500(4) 0.0789 1.0000 Uani . . . . . . C17 C 0.4958(9) -0.0473(9) 0.8273(5) 0.0774 1.0000 Uani . . . . . . C18 C 0.2895(7) 0.1850(6) 0.7135(4) 0.0505 1.0000 Uani . . . . . . C19 C 0.1591(8) 0.1681(8) 0.7448(5) 0.0666 1.0000 Uani . . . . . . C20 C 0.2761(10) 0.2087(8) 0.6397(5) 0.0726 1.0000 Uani . . . . . . C21 C 0.8086(7) 0.2086(6) 0.5550(4) 0.0492 1.0000 Uani . . . . . . C22 C 0.7001(10) 0.2842(7) 0.5371(5) 0.0699 1.0000 Uani . . . . . . C23 C 0.8977(9) 0.2554(7) 0.6084(5) 0.0757 1.0000 Uani . . . . . . C24 C 0.8784(7) -0.0053(7) 0.6022(4) 0.0562 1.0000 Uani . . . . . . C25 C 0.9757(9) -0.0165(8) 0.5462(6) 0.0779 1.0000 Uani . . . . . . C26 C 0.8285(10) -0.1095(7) 0.6259(5) 0.0706 1.0000 Uani . . . . . . N1 N 0.4840(5) -0.0105(4) 0.5956(3) 0.0348 1.0000 Uani . . . . . . H31 H 0.2083 -0.0744 0.7620 0.0703 1.0000 Uiso . . . . . . H41 H 0.1203 -0.2250 0.7137 0.0824 1.0000 Uiso . . . . . . H51 H 0.1777 -0.2697 0.6083 0.0743 1.0000 Uiso . . . . . . H71 H 0.4264 -0.2248 0.5219 0.0810 1.0000 Uiso . . . . . . H72 H 0.2808 -0.2471 0.5123 0.0810 1.0000 Uiso . . . . . . H81 H 0.2704 -0.0546 0.4922 0.0850 1.0000 Uiso . . . . . . H82 H 0.3090 -0.1280 0.4339 0.0850 1.0000 Uiso . . . . . . H101 H 0.4673 -0.0663 0.3727 0.0658 1.0000 Uiso . . . . . . H111 H 0.6712 0.0018 0.3550 0.0712 1.0000 Uiso . . . . . . H121 H 0.7873 0.0620 0.4459 0.0601 1.0000 Uiso . . . . . . H151 H 0.3259 0.0342 0.8287 0.0685 1.0000 Uiso . . . . . . H161 H 0.4646 0.1331 0.8963 0.1025 1.0000 Uiso . . . . . . H162 H 0.5452 0.1634 0.8344 0.1025 1.0000 Uiso . . . . . . H163 H 0.4054 0.2048 0.8419 0.1025 1.0000 Uiso . . . . . . H171 H 0.4985 -0.0601 0.8738 0.1006 1.0000 Uiso . . . . . . H172 H 0.5804 -0.0341 0.8115 0.1006 1.0000 Uiso . . . . . . H173 H 0.4613 -0.1072 0.8053 0.1006 1.0000 Uiso . . . . . . H181 H 0.3266 0.2453 0.7339 0.0657 1.0000 Uiso . . . . . . H191 H 0.1067 0.2282 0.7372 0.0866 1.0000 Uiso . . . . . . H192 H 0.1690 0.1576 0.7912 0.0866 1.0000 Uiso . . . . . . H193 H 0.1196 0.1078 0.7256 0.0866 1.0000 Uiso . . . . . . H201 H 0.2173 0.2652 0.6336 0.0944 1.0000 Uiso . . . . . . H202 H 0.3577 0.2277 0.6221 0.0944 1.0000 Uiso . . . . . . H203 H 0.2449 0.1479 0.6173 0.0944 1.0000 Uiso . . . . . . H211 H 0.8579 0.1947 0.5163 0.0640 1.0000 Uiso . . . . . . H221 H 0.7356 0.3485 0.5212 0.0909 1.0000 Uiso . . . . . . H222 H 0.6492 0.2976 0.5753 0.0909 1.0000 Uiso . . . . . . H223 H 0.6480 0.2536 0.5035 0.0909 1.0000 Uiso . . . . . . H231 H 0.9329 0.3199 0.5928 0.0985 1.0000 Uiso . . . . . . H232 H 0.9655 0.2072 0.6175 0.0985 1.0000 Uiso . . . . . . H233 H 0.8498 0.2678 0.6478 0.0985 1.0000 Uiso . . . . . . H241 H 0.9239 0.0246 0.6385 0.0730 1.0000 Uiso . . . . . . H251 H 1.0422 -0.0634 0.5595 0.1013 1.0000 Uiso . . . . . . H252 H 1.0116 0.0505 0.5363 0.1013 1.0000 Uiso . . . . . . H253 H 0.9339 -0.0437 0.5079 0.1013 1.0000 Uiso . . . . . . H261 H 0.8987 -0.1555 0.6344 0.0918 1.0000 Uiso . . . . . . H262 H 0.7803 -0.0997 0.6655 0.0918 1.0000 Uiso . . . . . . H263 H 0.7747 -0.1395 0.5928 0.0918 1.0000 Uiso . . . . . . 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 Rh1 0.02977(19) 0.0443(2) 0.0350(2) -0.0077(2) 0.0038(2) -0.0090(2) P1 0.0300(6) 0.0454(9) 0.0319(6) -0.0002(7) 0.0032(6) -0.0050(8) P2 0.0288(6) 0.0390(8) 0.0388(7) -0.0013(8) 0.0040(6) -0.0041(8) C1 0.032(3) 0.028(3) 0.039(3) 0.006(2) -0.005(2) -0.004(2) C2 0.031(3) 0.047(4) 0.043(3) 0.010(3) 0.000(3) -0.007(3) C3 0.044(3) 0.068(5) 0.050(3) 0.012(4) 0.003(3) -0.015(4) C4 0.053(4) 0.061(5) 0.076(6) 0.024(5) -0.007(4) -0.020(4) C5 0.041(4) 0.047(4) 0.084(6) 0.009(4) -0.013(4) -0.014(3) C6 0.043(3) 0.038(3) 0.054(4) -0.001(3) -0.016(3) -0.005(3) C7 0.064(5) 0.048(4) 0.075(6) -0.016(4) -0.004(4) -0.020(4) C8 0.063(5) 0.077(6) 0.056(4) -0.014(5) -0.023(4) -0.008(5) C9 0.046(3) 0.048(4) 0.040(3) -0.005(3) -0.012(3) 0.003(3) C10 0.065(5) 0.048(4) 0.039(4) -0.012(3) -0.013(4) 0.012(4) C11 0.068(5) 0.066(5) 0.030(3) -0.009(3) -0.003(3) 0.012(4) C12 0.048(4) 0.053(4) 0.038(3) -0.005(3) 0.007(3) 0.002(3) C13 0.037(3) 0.039(3) 0.038(3) -0.008(3) 0.006(3) 0.003(3) C14 0.038(3) 0.024(3) 0.041(3) -0.004(2) -0.006(3) 0.004(2) C15 0.047(3) 0.077(5) 0.035(3) 0.006(3) 0.007(3) -0.022(4) C16 0.088(7) 0.107(8) 0.041(5) -0.010(4) -0.004(4) -0.028(6) C17 0.066(5) 0.092(7) 0.074(6) 0.028(5) -0.019(5) -0.021(5) C18 0.042(4) 0.048(4) 0.061(5) -0.013(4) 0.008(3) 0.001(3) C19 0.052(5) 0.081(6) 0.067(5) 0.000(5) 0.014(4) 0.017(4) C20 0.072(6) 0.072(6) 0.074(5) 0.025(5) -0.004(5) 0.014(5) C21 0.051(4) 0.040(4) 0.056(4) -0.003(3) 0.013(4) -0.006(3) C22 0.082(6) 0.049(4) 0.079(6) 0.018(4) 0.003(5) 0.008(4) C23 0.064(6) 0.062(5) 0.101(6) -0.003(5) -0.019(5) -0.030(5) C24 0.042(4) 0.068(5) 0.059(4) 0.011(4) 0.002(3) 0.005(3) C25 0.058(5) 0.076(6) 0.100(8) 0.016(6) 0.032(5) 0.030(5) C26 0.077(6) 0.053(5) 0.081(6) 0.025(4) 0.009(5) 0.008(5) N1 0.031(2) 0.034(3) 0.039(3) -0.002(2) -0.002(2) -0.001(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.3048(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Rh1 . P1 . 2.2457(16) yes Rh1 . P2 . 2.2428(14) yes Rh1 . N1 . 2.096(5) yes P1 . C2 . 1.795(7) yes P1 . C15 . 1.840(6) yes P1 . C18 . 1.844(8) yes P2 . C13 . 1.790(7) yes P2 . C21 . 1.848(7) yes P2 . C24 . 1.847(8) yes C1 . C2 . 1.418(9) yes C1 . C6 . 1.431(9) yes C1 . N1 . 1.423(7) yes C2 . C3 . 1.414(9) yes C3 . C4 . 1.376(13) yes C3 . H31 . 0.950 no C4 . C5 . 1.341(13) yes C4 . H41 . 0.950 no C5 . C6 . 1.404(11) yes C5 . H51 . 0.950 no C6 . C7 . 1.503(12) yes C7 . C8 . 1.517(13) yes C7 . H71 . 0.950 no C7 . H72 . 0.950 no C8 . C9 . 1.485(12) yes C8 . H81 . 0.950 no C8 . H82 . 0.950 no C9 . C10 . 1.382(11) yes C9 . C14 . 1.430(9) yes C10 . C11 . 1.374(12) yes C10 . H101 . 0.950 no C11 . C12 . 1.370(11) yes C11 . H111 . 0.950 no C12 . C13 . 1.396(9) yes C12 . H121 . 0.950 no C13 . C14 . 1.432(9) yes C14 . N1 . 1.421(8) yes C15 . C16 . 1.540(13) yes C15 . C17 . 1.533(14) yes C15 . H151 . 0.950 no C16 . H161 . 0.950 no C16 . H162 . 0.950 no C16 . H163 . 0.950 no C17 . H171 . 0.950 no C17 . H172 . 0.950 no C17 . H173 . 0.950 no C18 . C19 . 1.509(11) yes C18 . C20 . 1.524(13) yes C18 . H181 . 0.950 no C19 . H191 . 0.950 no C19 . H192 . 0.950 no C19 . H193 . 0.950 no C20 . H201 . 0.950 no C20 . H202 . 0.950 no C20 . H203 . 0.950 no C21 . C22 . 1.523(12) yes C21 . C23 . 1.538(12) yes C21 . H211 . 0.950 no C22 . H221 . 0.950 no C22 . H222 . 0.950 no C22 . H223 . 0.950 no C23 . H231 . 0.950 no C23 . H232 . 0.950 no C23 . H233 . 0.950 no C24 . C25 . 1.521(12) yes C24 . C26 . 1.500(12) yes C24 . H241 . 0.950 no C25 . H251 . 0.950 no C25 . H252 . 0.950 no C25 . H253 . 0.950 no C26 . H261 . 0.950 no C26 . H262 . 0.950 no C26 . H263 . 0.950 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag P1 . Rh1 . P2 . 169.11(6) yes P1 . Rh1 . N1 . 84.41(15) yes P2 . Rh1 . N1 . 84.82(15) yes Rh1 . P1 . C2 . 99.6(2) yes Rh1 . P1 . C15 . 121.6(3) yes C2 . P1 . C15 . 107.3(3) yes Rh1 . P1 . C18 . 115.1(3) yes C2 . P1 . C18 . 106.3(3) yes C15 . P1 . C18 . 105.6(4) yes Rh1 . P2 . C13 . 100.0(2) yes Rh1 . P2 . C21 . 119.3(2) yes C13 . P2 . C21 . 105.1(3) yes Rh1 . P2 . C24 . 117.0(3) yes C13 . P2 . C24 . 107.1(4) yes C21 . P2 . C24 . 106.8(4) yes C2 . C1 . C6 . 114.7(6) yes C2 . C1 . N1 . 117.4(5) yes C6 . C1 . N1 . 127.7(6) yes P1 . C2 . C1 . 117.4(4) yes P1 . C2 . C3 . 120.3(6) yes C1 . C2 . C3 . 122.2(7) yes C2 . C3 . C4 . 120.4(7) yes C2 . C3 . H31 . 119.8 no C4 . C3 . H31 . 119.8 no C3 . C4 . C5 . 118.9(8) yes C3 . C4 . H41 . 120.6 no C5 . C4 . H41 . 120.6 no C4 . C5 . C6 . 123.0(8) yes C4 . C5 . H51 . 118.5 no C6 . C5 . H51 . 118.5 no C1 . C6 . C5 . 120.6(7) yes C1 . C6 . C7 . 122.3(6) yes C5 . C6 . C7 . 116.8(7) yes C6 . C7 . C8 . 110.2(7) yes C6 . C7 . H71 . 109.3 no C8 . C7 . H71 . 109.3 no C6 . C7 . H72 . 109.3 no C8 . C7 . H72 . 109.3 no H71 . C7 . H72 . 109.5 no C7 . C8 . C9 . 109.7(7) yes C7 . C8 . H81 . 109.4 no C9 . C8 . H81 . 109.4 no C7 . C8 . H82 . 109.4 no C9 . C8 . H82 . 109.4 no H81 . C8 . H82 . 109.5 no C8 . C9 . C10 . 117.2(6) yes C8 . C9 . C14 . 122.8(7) yes C10 . C9 . C14 . 119.8(7) yes C9 . C10 . C11 . 123.8(7) yes C9 . C10 . H101 . 118.1 no C11 . C10 . H101 . 118.1 no C10 . C11 . C12 . 117.2(7) yes C10 . C11 . H111 . 121.4 no C12 . C11 . H111 . 121.4 no C11 . C12 . C13 . 122.5(7) yes C11 . C12 . H121 . 118.7 no C13 . C12 . H121 . 118.7 no P2 . C13 . C12 . 121.5(5) yes P2 . C13 . C14 . 118.0(5) yes C12 . C13 . C14 . 120.5(6) yes C13 . C14 . C9 . 116.1(6) yes C13 . C14 . N1 . 116.8(6) yes C9 . C14 . N1 . 126.9(6) yes P1 . C15 . C16 . 109.7(6) yes P1 . C15 . C17 . 110.2(6) yes C16 . C15 . C17 . 111.0(7) yes P1 . C15 . H151 . 108.6 no C16 . C15 . H151 . 108.6 no C17 . C15 . H151 . 108.6 no C15 . C16 . H161 . 109.5 no C15 . C16 . H162 . 109.5 no H161 . C16 . H162 . 109.5 no C15 . C16 . H163 . 109.5 no H161 . C16 . H163 . 109.5 no H162 . C16 . H163 . 109.5 no C15 . C17 . H171 . 109.5 no C15 . C17 . H172 . 109.5 no H171 . C17 . H172 . 109.5 no C15 . C17 . H173 . 109.5 no H171 . C17 . H173 . 109.5 no H172 . C17 . H173 . 109.5 no P1 . C18 . C19 . 115.2(6) yes P1 . C18 . C20 . 108.4(6) yes C19 . C18 . C20 . 110.7(7) yes P1 . C18 . H181 . 107.4 no C19 . C18 . H181 . 107.4 no C20 . C18 . H181 . 107.4 no C18 . C19 . H191 . 109.5 no C18 . C19 . H192 . 109.5 no H191 . C19 . H192 . 109.5 no C18 . C19 . H193 . 109.5 no H191 . C19 . H193 . 109.5 no H192 . C19 . H193 . 109.5 no C18 . C20 . H201 . 109.5 no C18 . C20 . H202 . 109.5 no H201 . C20 . H202 . 109.5 no C18 . C20 . H203 . 109.5 no H201 . C20 . H203 . 109.5 no H202 . C20 . H203 . 109.5 no P2 . C21 . C22 . 109.9(6) yes P2 . C21 . C23 . 109.0(6) yes C22 . C21 . C23 . 111.6(8) yes P2 . C21 . H211 . 108.7 no C22 . C21 . H211 . 108.7 no C23 . C21 . H211 . 108.7 no C21 . C22 . H221 . 109.5 no C21 . C22 . H222 . 109.5 no H221 . C22 . H222 . 109.5 no C21 . C22 . H223 . 109.5 no H221 . C22 . H223 . 109.5 no H222 . C22 . H223 . 109.5 no C21 . C23 . H231 . 109.5 no C21 . C23 . H232 . 109.5 no H231 . C23 . H232 . 109.5 no C21 . C23 . H233 . 109.5 no H231 . C23 . H233 . 109.5 no H232 . C23 . H233 . 109.5 no P2 . C24 . C25 . 116.0(6) yes P2 . C24 . C26 . 109.0(6) yes C25 . C24 . C26 . 112.5(8) yes P2 . C24 . H241 . 106.2 no C25 . C24 . H241 . 106.2 no C26 . C24 . H241 . 106.2 no C24 . C25 . H251 . 109.5 no C24 . C25 . H252 . 109.5 no H251 . C25 . H252 . 109.5 no C24 . C25 . H253 . 109.5 no H251 . C25 . H253 . 109.5 no H252 . C25 . H253 . 109.5 no C24 . C26 . H261 . 109.5 no C24 . C26 . H262 . 109.5 no H261 . C26 . H262 . 109.5 no C24 . C26 . H263 . 109.5 no H261 . C26 . H263 . 109.5 no H262 . C26 . H263 . 109.5 no C1 . N1 . C14 . 126.2(5) yes C1 . N1 . Rh1 . 116.6(4) yes C14 . N1 . Rh1 . 117.2(4) yes # Attachment 'Compound3b.cif' data_3b_cif _database_code_depnum_ccdc_archive 'CCDC 281663' _audit_creation_date 05-09-30 _audit_creation_method CRYSTALS_ver_12.80 _oxford_structure_analysis_title OZ022 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 18.053(14) _cell_length_b 18.053(14) _cell_length_c 16.603(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 5411(6) _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M 'I 41/a ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z+1/2 -x+1/2,-y+1/2,-z+1/2 -y+3/4,x+1/4,z+1/4 y+3/4,-x+1/4,-z+1/4 -y+5/4,x+3/4,z+3/4 y+5/4,-x+3/4,-z+3/4 -x+1/2,-y,z+1/2 x+1/2,y,-z+1/2 -x+1,-y+1/2,z+1 x+1,y+1/2,-z+1 y+3/4,-x+3/4,z+3/4 -y+3/4,x+3/4,-z+3/4 y+5/4,-x+5/4,z+5/4 -y+5/4,x+5/4,-z+5/4 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source Rh -1.1178 0.9187 19.2957 0.7515 14.3501 8.2176 4.7343 25.8749 1.2892 98.6062 5.3280 'International Tables Vol C 4.2.6.8 and 6.1.1.4' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C26 H42 N1 P2 Rh1 # Dc = 1.31 Fooo = 2224.00 Mu = 7.62 M = 266.74 # Found Formula = C26 H40 N1 P2 Rh1 # Dc = 1.30 FOOO = 2224.00 Mu = 7.62 M = 265.73 _chemical_formula_sum 'C26 H42 N1 P2 Rh1' _chemical_formula_moiety 'C26 H42 N1 P2 Rh1' _chemical_compound_source ? _chemical_formula_weight 533.48 _cell_measurement_reflns_used 15 _cell_measurement_theta_min 9 _cell_measurement_theta_max 14 _cell_measurement_temperature 294 _exptl_crystal_description diamond _exptl_crystal_colour red-orange _exptl_crystal_size_min 0.14 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_max 0.29 _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 2240 _exptl_absorpt_coefficient_mu 0.765 # Sheldrick geometric approximatio 0.80 0.90 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; Azimutal absorption correction (North et al., 1968) ; _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_T_max 0.90 _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \\w _computing_data_collection 'CAD4 Express, (Straver, 1992)' _computing_data_reduction 'RC93 (Watkin, Prout & Lilley, 1994)' _computing_cell_refinement 'CAD4 Express, (Straver, 1992)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 3 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 294 _diffrn_reflns_number 2209 _reflns_number_total 2050 _diffrn_reflns_av_R_equivalents 0.044 # Number of reflections with Friedels Law is 2050 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2045 _diffrn_reflns_theta_min 2.805 _diffrn_reflns_theta_max 23.678 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 23.678 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min 0 _reflns_limit_h_max 20 _reflns_limit_k_min 0 _reflns_limit_k_max 20 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.69 _refine_diff_density_max 0.57 _refine_ls_number_reflns 913 _refine_ls_number_restraints 0 _refine_ls_number_parameters 137 #_refine_ls_R_factor_ref 0.0578 _refine_ls_wR_factor_ref 0.0534 _refine_ls_goodness_of_fit_ref 1.1625 #_reflns_number_all 2050 _refine_ls_R_factor_all 0.2127 _refine_ls_wR_factor_all 0.1397 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 913 _refine_ls_R_factor_gt 0.0578 _refine_ls_wR_factor_gt 0.0534 _refine_ls_shift/su_max 0.000307 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.24 -0.443 0.922 ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens P1 P 1.01064(16) 0.37530(16) 0.24405(18) 0.0388 1.0000 Uani . . . . . . Rh1 Rh 1.0000 0.2500 0.21583(8) 0.0365 1.0000 Uani S T . . . . N1 N 1.0000 0.2500 0.3432(7) 0.0431 1.0000 Uani S T . . . . C1 C 1.0391(6) 0.3040(5) 0.3827(8) 0.0411 1.0000 Uani . . . . . . C2 C 1.0531(6) 0.3714(6) 0.3436(6) 0.0370 1.0000 Uani . . . . . . C3 C 1.0911(6) 0.4277(5) 0.3806(7) 0.0373 1.0000 Uani . . . . . . C4 C 1.1197(6) 0.4200(6) 0.4600(8) 0.0460 1.0000 Uani . . . . . . C5 C 1.1077(8) 0.3532(8) 0.4959(8) 0.0634 1.0000 Uani . . . . . . C6 C 1.0697(6) 0.2963(6) 0.4620(8) 0.0468 1.0000 Uani . . . . . . C7 C 1.1607(8) 0.4829(8) 0.4982(8) 0.0705 1.0000 Uani . . . . . . C8 C 1.0691(7) 0.4427(6) 0.1899(7) 0.0410 1.0000 Uani . . . . . . C9 C 1.1480(8) 0.4128(7) 0.1836(8) 0.0617 1.0000 Uani . . . . . . C10 C 1.0384(8) 0.4615(7) 0.1065(8) 0.0678 1.0000 Uani . . . . . . C11 C 0.9237(6) 0.4270(7) 0.2633(7) 0.0547 1.0000 Uani . . . . . . C12 C 0.8764(8) 0.3834(8) 0.3222(9) 0.0730 1.0000 Uani . . . . . . C13 C 0.9358(8) 0.5061(7) 0.2938(9) 0.0728 1.0000 Uani . . . . . . H31 H 1.0985 0.4730 0.3525 0.0485 1.0000 Uiso . . . . . . H51 H 1.1274 0.3459 0.5484 0.0825 1.0000 Uiso . . . . . . H61 H 1.0633 0.2513 0.4909 0.0608 1.0000 Uiso . . . . . . H71 H 1.1539 0.4814 0.5549 0.0917 1.0000 Uiso . . . . . . H72 H 1.2120 0.4787 0.4862 0.0917 1.0000 Uiso . . . . . . H73 H 1.1424 0.5285 0.4778 0.0917 1.0000 Uiso . . . . . . H81 H 1.0706 0.4871 0.2207 0.0533 1.0000 Uiso . . . . . . H91 H 1.1781 0.4475 0.1557 0.0803 1.0000 Uiso . . . . . . H92 H 1.1674 0.4050 0.2361 0.0803 1.0000 Uiso . . . . . . H93 H 1.1475 0.3672 0.1550 0.0803 1.0000 Uiso . . . . . . H101 H 1.0701 0.4963 0.0809 0.0882 1.0000 Uiso . . . . . . H102 H 1.0358 0.4177 0.0749 0.0882 1.0000 Uiso . . . . . . H103 H 0.9903 0.4822 0.1119 0.0882 1.0000 Uiso . . . . . . H111 H 0.8973 0.4300 0.2138 0.0711 1.0000 Uiso . . . . . . H121 H 0.8318 0.4096 0.3323 0.0949 1.0000 Uiso . . . . . . H122 H 0.9028 0.3771 0.3712 0.0949 1.0000 Uiso . . . . . . H123 H 0.8652 0.3363 0.2999 0.0949 1.0000 Uiso . . . . . . H131 H 0.8892 0.5292 0.3023 0.0946 1.0000 Uiso . . . . . . H132 H 0.9625 0.5047 0.3430 0.0946 1.0000 Uiso . . . . . . H133 H 0.9631 0.5334 0.2549 0.0946 1.0000 Uiso . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0400(17) 0.0360(16) 0.0404(18) -0.0023(14) 0.0005(14) -0.0006(14) Rh1 0.0396(11) 0.0360(11) 0.0339(6) 0.0000 0.0000 -0.0033(10) N1 0.065(12) 0.026(9) 0.038(7) 0.0000 0.0000 -0.019(9) C1 0.046(6) 0.031(6) 0.046(7) -0.006(6) 0.011(7) 0.008(5) C2 0.036(7) 0.036(7) 0.039(6) 0.001(5) -0.003(5) 0.000(5) C3 0.052(7) 0.024(6) 0.036(6) -0.010(6) 0.000(7) 0.003(5) C4 0.033(6) 0.047(7) 0.058(8) -0.016(7) -0.002(6) -0.004(5) C5 0.063(9) 0.066(9) 0.061(9) -0.008(8) -0.001(7) 0.003(8) C6 0.052(7) 0.049(7) 0.040(7) 0.008(6) 0.002(6) -0.019(6) C7 0.068(9) 0.079(10) 0.065(8) -0.028(8) -0.009(8) -0.019(8) C8 0.058(8) 0.025(6) 0.040(7) 0.007(5) 0.004(6) -0.015(6) C9 0.060(9) 0.061(9) 0.064(9) 0.004(7) 0.015(7) -0.017(7) C10 0.071(9) 0.065(8) 0.067(11) 0.019(8) 0.001(7) -0.011(7) C11 0.037(6) 0.078(9) 0.049(8) -0.009(7) 0.000(6) 0.007(6) C12 0.061(9) 0.064(9) 0.095(11) -0.025(8) 0.021(8) 0.009(8) C13 0.074(9) 0.055(8) 0.090(12) -0.016(8) 0.029(9) 0.018(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.0706(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag P1 . Rh1 . 2.318(3) yes P1 . C2 . 1.824(11) yes P1 . C8 . 1.845(11) yes P1 . C11 . 1.854(12) yes Rh1 . N1 . 2.115(12) yes N1 . C1 11_654 1.370(12) yes N1 . C1 . 1.370(12) yes C1 . C2 . 1.403(15) yes C1 . C6 . 1.435(17) yes C2 . C3 . 1.371(14) yes C3 . C4 . 1.423(16) yes C3 . H31 . 0.950 no C4 . C5 . 1.363(18) yes C4 . C7 . 1.498(16) yes C5 . C6 . 1.357(17) yes C5 . H51 . 0.950 no C6 . H61 . 0.950 no C7 . H71 . 0.950 no C7 . H72 . 0.950 no C7 . H73 . 0.950 no C8 . C9 . 1.526(17) yes C8 . C10 . 1.530(17) yes C8 . H81 . 0.950 no C9 . H91 . 0.950 no C9 . H92 . 0.950 no C9 . H93 . 0.950 no C10 . H101 . 0.950 no C10 . H102 . 0.950 no C10 . H103 . 0.950 no C11 . C12 . 1.518(19) yes C11 . C13 . 1.531(17) yes C11 . H111 . 0.950 no C12 . H121 . 0.950 no C12 . H122 . 0.950 no C12 . H123 . 0.950 no C13 . H131 . 0.950 no C13 . H132 . 0.950 no C13 . H133 . 0.950 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag Rh1 . P1 . C2 . 100.4(4) yes Rh1 . P1 . C8 . 126.4(4) yes C2 . P1 . C8 . 103.1(5) yes Rh1 . P1 . C11 . 117.1(4) yes C2 . P1 . C11 . 102.7(5) yes C8 . P1 . C11 . 103.7(6) yes P1 . Rh1 . P1 11_654 156.68(16) yes P1 . Rh1 . N1 . 78.34(9) yes P1 11_654 Rh1 . N1 . 78.34(9) yes C1 11_654 N1 . Rh1 . 118.6(7) yes C1 11_654 N1 . C1 . 122.8(14) yes Rh1 . N1 . C1 . 118.6(7) yes N1 . C1 . C2 . 119.3(11) yes N1 . C1 . C6 . 124.7(10) yes C2 . C1 . C6 . 116.0(10) yes P1 . C2 . C1 . 112.1(9) yes P1 . C2 . C3 . 126.0(9) yes C1 . C2 . C3 . 121.8(10) yes C2 . C3 . C4 . 121.5(10) yes C2 . C3 . H31 . 119.2 no C4 . C3 . H31 . 119.2 no C3 . C4 . C5 . 115.8(11) yes C3 . C4 . C7 . 119.8(11) yes C5 . C4 . C7 . 124.4(12) yes C4 . C5 . C6 . 124.6(13) yes C4 . C5 . H51 . 117.7 no C6 . C5 . H51 . 117.7 no C1 . C6 . C5 . 120.2(11) yes C1 . C6 . H61 . 119.9 no C5 . C6 . H61 . 119.9 no C4 . C7 . H71 . 109.5 no C4 . C7 . H72 . 109.4 no H71 . C7 . H72 . 109.4 no C4 . C7 . H73 . 109.5 no H71 . C7 . H73 . 109.5 no H72 . C7 . H73 . 109.5 no P1 . C8 . C9 . 109.5(8) yes P1 . C8 . C10 . 112.3(9) yes C9 . C8 . C10 . 110.8(10) yes P1 . C8 . H81 . 108.0 no C9 . C8 . H81 . 108.1 no C10 . C8 . H81 . 108.0 no C8 . C9 . H91 . 109.4 no C8 . C9 . H92 . 109.5 no H91 . C9 . H92 . 109.5 no C8 . C9 . H93 . 109.5 no H91 . C9 . H93 . 109.5 no H92 . C9 . H93 . 109.5 no C8 . C10 . H101 . 109.5 no C8 . C10 . H102 . 109.4 no H101 . C10 . H102 . 109.5 no C8 . C10 . H103 . 109.5 no H101 . C10 . H103 . 109.5 no H102 . C10 . H103 . 109.5 no P1 . C11 . C12 . 109.0(9) yes P1 . C11 . C13 . 113.9(9) yes C12 . C11 . C13 . 110.5(11) yes P1 . C11 . H111 . 107.7 no C12 . C11 . H111 . 107.7 no C13 . C11 . H111 . 107.7 no C11 . C12 . H121 . 109.5 no C11 . C12 . H122 . 109.5 no H121 . C12 . H122 . 109.5 no C11 . C12 . H123 . 109.5 no H121 . C12 . H123 . 109.5 no H122 . C12 . H123 . 109.5 no C11 . C13 . H131 . 109.4 no C11 . C13 . H132 . 109.5 no H131 . C13 . H132 . 109.5 no C11 . C13 . H133 . 109.5 no H131 . C13 . H133 . 109.5 no H132 . C13 . H133 . 109.5 no