# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_DPATPAN _database_code_depnum_ccdc_archive 'CCDC 915768' #TrackingRef '16191_web_deposit_cif_file_0_WangZhangYuan_1355486241.DPATPAN.cif' _chemical_name_common 2-(4-(diphenylamino)phenyl)-3,3-diphenylacrylonitrile _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H24 N2' _chemical_formula_weight 448.56 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 12.057(9) _cell_length_b 10.242(7) _cell_length_c 21.011(15) _cell_angle_alpha 90.00 _cell_angle_beta 103.453(9) _cell_angle_gamma 90.00 _cell_volume 2523.41 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z C7 C -0.02531(11) 0.26111(12) 0.01186(6) N1 N 0.53466(10) 0.28813(11) 0.13580(6) C18 C 0.42041(11) 0.27354(13) 0.09969(6) C13 C -0.01881(11) 0.30448(14) 0.08053(6) C6 C -0.14263(11) 0.25397(13) -0.03116(6) C14 C 0.07030(11) 0.22604(13) -0.00770(6) C26 C 0.54371(12) 0.08429(15) 0.19725(7) H26A H 0.4658 0.0894 0.1946 C16 C 0.22857(11) 0.35838(13) 0.06358(6) H16A H 0.1772 0.4263 0.0632 C21 C 0.59735(11) 0.18117(13) 0.16888(6) C20 C 0.27147(12) 0.14561(13) 0.03081(7) H20A H 0.2491 0.0688 0.0077 C27 C 0.58803(11) 0.41354(13) 0.13946(7) C17 C 0.34111(11) 0.37350(13) 0.09757(6) H17A H 0.3640 0.4515 0.1193 C15 C 0.19097(11) 0.24360(13) 0.03006(6) C1 C -0.23397(13) 0.21562(15) -0.00466(8) H1A H -0.2207 0.1946 0.0395 C19 C 0.38400(12) 0.15947(14) 0.06503(7) H19A H 0.4356 0.0920 0.0648 C5 C -0.16633(13) 0.28707(14) -0.09715(7) H5A H -0.1077 0.3152 -0.1158 C8 C -0.06598(13) 0.42295(15) 0.09284(7) H8A H -0.0991 0.4770 0.0581 C32 C 0.59163(13) 0.47963(15) 0.08257(8) H32A H 0.5618 0.4410 0.0422 C25 C 0.60568(13) -0.01937(15) 0.22932(8) H25A H 0.5687 -0.0843 0.2474 C22 C 0.71409(12) 0.17190(15) 0.17418(7) H22A H 0.7514 0.2356 0.1555 C33 C 0.06103(12) 0.16300(16) -0.06999(8) C12 C 0.02830(13) 0.22393(16) 0.13278(7) H12A H 0.0605 0.1444 0.1256 C28 C 0.63654(12) 0.47023(16) 0.19908(8) H28A H 0.6373 0.4256 0.2377 C4 C -0.27678(15) 0.27858(17) -0.13553(8) H4A H -0.2911 0.2999 -0.1797 C2 C -0.34399(13) 0.20862(17) -0.04350(9) H2A H -0.4037 0.1832 -0.0251 C30 C 0.68472(14) 0.66052(17) 0.14446(10) H30A H 0.7157 0.7439 0.1462 C3 C -0.36517(14) 0.23898(17) -0.10889(10) H3A H -0.4387 0.2328 -0.1350 C31 C 0.63937(14) 0.60290(16) 0.08545(9) H31A H 0.6406 0.6470 0.0469 C11 C 0.02715(14) 0.2628(2) 0.19626(8) H11A H 0.0579 0.2085 0.2314 C29 C 0.68405(14) 0.59396(17) 0.20120(9) H29A H 0.7158 0.6323 0.2414 C10 C -0.01923(15) 0.3812(2) 0.20719(8) H10A H -0.0198 0.4066 0.2496 C24 C 0.72112(14) -0.02778(16) 0.23480(8) H24A H 0.7625 -0.0974 0.2569 C23 C 0.77504(13) 0.06784(17) 0.20725(9) H23A H 0.8533 0.0626 0.2108 C9 C -0.06434(14) 0.4613(2) 0.15589(8) H9A H -0.0941 0.5421 0.1635 N2 N 0.05940(14) 0.11108(19) -0.11837(8) data_MeDPATPAN _database_code_depnum_ccdc_archive 'CCDC 915769' #TrackingRef '16192_web_deposit_cif_file_1_WangZhangYuan_1355486241.MeDPATPAN.cif' _chemical_name_common 3,3-diphenyl-2-(4-(phenyl(p-tolyl)amino)phenyl)acrylonitrile _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H26 N2' _chemical_formula_weight 462.58 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_Int_Tables_number 9 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 x,-y,1/2+z 3 1/2+x,1/2+y,z 4 1/2+x,1/2-y,1/2+z _cell_length_a 14.165(3) _cell_length_b 13.763(3) _cell_length_c 13.176(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.685(2) _cell_angle_gamma 90.00 _cell_volume 2560.12 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z N1 N -0.10151(15) 0.01972(16) 0.42196(19) C32 C 0.27622(17) 0.19729(18) 0.23696(19) C33 C 0.26099(17) 0.11349(18) 0.2895(2) C16 C 0.15931(18) 0.03591(19) 0.4139(2) H16 H 0.2138 0.0199 0.4546 C14 C -0.01037(17) 0.03522(19) 0.3868(2) C17 C 0.16768(17) 0.08088(17) 0.3204(2) C34 C 0.3403(2) 0.05397(19) 0.3254(2) C18 C 0.08524(18) 0.0952(2) 0.2574(2) H18 H 0.0892 0.1196 0.1921 C7 C -0.12137(17) -0.06642(19) 0.47625(19) C24 C 0.17923(19) 0.3199(2) 0.1341(2) H24 H 0.2111 0.3038 0.0775 C19 C -0.00275(19) 0.0735(2) 0.2905(2) H19 H -0.0572 0.0847 0.2478 C15 C 0.07197(19) 0.0146(2) 0.4474(2) H15 H 0.0682 -0.0137 0.5110 C5 C -0.20588(19) -0.1515(2) 0.6001(2) H5 H -0.2496 -0.1499 0.6491 C13 C -0.17326(17) 0.09119(19) 0.4003(2) C21 C 0.08395(19) 0.3706(2) 0.3008(2) H21 H 0.0515 0.3874 0.3569 C25 C 0.20313(17) 0.27447(17) 0.2265(2) C20 C 0.15571(18) 0.30211(18) 0.3106(2) H20 H 0.1725 0.2743 0.3739 C6 C -0.18472(18) -0.0666(2) 0.5507(2) H6 H -0.2135 -0.0088 0.5678 C31 C 0.36655(17) 0.21582(18) 0.19084(19) C22 C 0.0609(2) 0.4134(2) 0.2085(3) H22 H 0.0127 0.4594 0.2020 C1 C -0.0779(2) -0.1538(2) 0.4551(2) H1 H -0.0342 -0.1556 0.4061 C27 C 0.4926(2) 0.3244(2) 0.1537(2) H27 H 0.5205 0.3855 0.1597 C8 C -0.26555(19) 0.0644(2) 0.3696(2) H8 H -0.2810 -0.0010 0.3618 C23 C 0.1082(2) 0.3892(2) 0.1256(2) H23 H 0.0925 0.4193 0.0633 C11 C -0.2213(3) 0.2586(2) 0.3890(2) H11 H -0.2061 0.3242 0.3951 C2 C -0.0983(2) -0.2375(2) 0.5053(2) H2 H -0.0677 -0.2948 0.4899 C4 C -0.16338(19) -0.2390(2) 0.5783(2) C29 C 0.4953(2) 0.1611(2) 0.0950(2) H29 H 0.5243 0.1122 0.0601 C12 C -0.1515(2) 0.1891(2) 0.4094(2) H12 H -0.0898 0.2083 0.4292 N2 N 0.40007(19) 0.00694(19) 0.3631(2) C26 C 0.40817(19) 0.30767(19) 0.1952(2) H26 H 0.3784 0.3584 0.2266 C30 C 0.41088(19) 0.1426(2) 0.1383(2) H30 H 0.3837 0.0811 0.1324 C28 C 0.5361(2) 0.2516(3) 0.1037(3) H28 H 0.5931 0.2636 0.0756 C3 C -0.1850(3) -0.3320(2) 0.6328(3) H3A H -0.1653 -0.3866 0.5944 H3B H -0.2518 -0.3361 0.6395 H3C H -0.1515 -0.3324 0.6992 C10 C -0.3125(3) 0.2316(3) 0.3599(3) H10 H -0.3592 0.2785 0.3466 C9 C -0.3346(2) 0.1343(3) 0.3505(2) H9 H -0.3965 0.1156 0.3311 data_PhNPATPAN _database_code_depnum_ccdc_archive 'CCDC 915770' #TrackingRef '16193_web_deposit_cif_file_2_WangZhangYuan_1355486241.PhNPATPAN.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 2-(4-(naphthalen-1-yl(phenyl)amino)phenyl)-3,3-diphenylacrylonitrile _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H26 N2' _chemical_formula_weight 498.60 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.118(3) _cell_length_b 12.072(3) _cell_length_c 12.647(3) _cell_angle_alpha 103.028(3) _cell_angle_beta 105.156(3) _cell_angle_gamma 104.109(4) _cell_volume 1375.3(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.204 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7671 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0614 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4757 _reflns_number_gt 2582 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0947P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4757 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1196 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1791 _refine_ls_wR_factor_gt 0.1530 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.975 _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 N1 N 0.9393(3) 0.5357(2) 0.2772(2) 0.0644(7) Uani 1 1 d . . . N2 N 0.5124(3) -0.0008(2) -0.1655(2) 0.0691(7) Uani 1 1 d . . . C1 C 0.8511(3) 0.5875(2) 0.3284(2) 0.0608(8) Uani 1 1 d . . . C2 C 0.7850(4) 0.5317(3) 0.3946(3) 0.0819(10) Uani 1 1 d . . . H2 H 0.7985 0.4604 0.4035 0.098 Uiso 1 1 calc R . . C3 C 0.7008(4) 0.5793(3) 0.4470(3) 0.0913(11) Uani 1 1 d . . . H3 H 0.6584 0.5414 0.4919 0.110 Uiso 1 1 calc R . . C4 C 0.6786(5) 0.6847(4) 0.4328(4) 0.1002(13) Uani 1 1 d . . . H4 H 0.6208 0.7180 0.4674 0.120 Uiso 1 1 calc R . . C5 C 0.7433(5) 0.7385(3) 0.3670(4) 0.0925(12) Uani 1 1 d . . . H5 H 0.7285 0.8091 0.3569 0.111 Uiso 1 1 calc R . . C6 C 0.8291(4) 0.6918(3) 0.3155(3) 0.0702(9) Uani 1 1 d . . . H6 H 0.8726 0.7308 0.2717 0.084 Uiso 1 1 calc R . . C7 C 1.0661(4) 0.6109(2) 0.2616(3) 0.0667(8) Uani 1 1 d . . . C8 C 1.0734(4) 0.6027(3) 0.1543(3) 0.0702(9) Uani 1 1 d . . . H8 H 0.9937 0.5518 0.0912 0.084 Uiso 1 1 calc R . . C9 C 1.1921(4) 0.6656(3) 0.1341(3) 0.0759(9) Uani 1 1 d . . . H9 H 1.1925 0.6565 0.0592 0.091 Uiso 1 1 calc R . . C10 C 1.3119(4) 0.7430(3) 0.2274(4) 0.0823(10) Uani 1 1 d . . . H10 H 1.3941 0.7854 0.2159 0.099 Uiso 1 1 calc R . . C11 C 1.3063(3) 0.7564(3) 0.3423(3) 0.0644(8) Uani 1 1 d . . . C12 C 1.4191(4) 0.8390(3) 0.4382(4) 0.0961(12) Uani 1 1 d . . . H12 H 1.4984 0.8874 0.4277 0.115 Uiso 1 1 calc R . . C13 C 1.4154(5) 0.8501(4) 0.5452(4) 0.1037(13) Uani 1 1 d . . . H13 H 1.4929 0.9039 0.6083 0.124 Uiso 1 1 calc R . . C14 C 1.2941(5) 0.7802(3) 0.5616(3) 0.0868(11) Uani 1 1 d . . . H14 H 1.2939 0.7881 0.6364 0.104 Uiso 1 1 calc R . . C15 C 1.1785(4) 0.7025(3) 0.4737(3) 0.0793(10) Uani 1 1 d . . . H15 H 1.0988 0.6587 0.4873 0.095 Uiso 1 1 calc R . . C16 C 1.1799(4) 0.6877(2) 0.3564(3) 0.0646(8) Uani 1 1 d . . . C17 C 0.8869(3) 0.4123(2) 0.2128(2) 0.0547(7) Uani 1 1 d . . . C18 C 0.7401(3) 0.3529(2) 0.1575(2) 0.0547(7) Uani 1 1 d . . . H18 H 0.6743 0.3941 0.1626 0.066 Uiso 1 1 calc R . . C19 C 0.6913(3) 0.2328(2) 0.0948(2) 0.0505(7) Uani 1 1 d . . . H19 H 0.5925 0.1944 0.0579 0.061 Uiso 1 1 calc R . . C20 C 0.7861(3) 0.1676(2) 0.0853(2) 0.0461(6) Uani 1 1 d . . . C21 C 0.9331(3) 0.2295(2) 0.1394(2) 0.0547(7) Uani 1 1 d . . . H21 H 0.9993 0.1890 0.1327 0.066 Uiso 1 1 calc R . . C22 C 0.9827(3) 0.3489(2) 0.2022(2) 0.0580(7) Uani 1 1 d . . . H22 H 1.0816 0.3878 0.2381 0.070 Uiso 1 1 calc R . . C23 C 0.7289(3) 0.0382(2) 0.0155(2) 0.0441(6) Uani 1 1 d . . . C24 C 0.6086(3) 0.0124(2) -0.0869(3) 0.0495(7) Uani 1 1 d . . . C25 C 0.7759(3) -0.0515(2) 0.0412(2) 0.0455(6) Uani 1 1 d . . . C26 C 0.7192(3) -0.1772(2) -0.0385(2) 0.0494(7) Uani 1 1 d . . . C27 C 0.6951(3) -0.2041(3) -0.1554(3) 0.0633(8) Uani 1 1 d . . . H27 H 0.7130 -0.1424 -0.1877 0.076 Uiso 1 1 calc R . . C28 C 0.6444(4) -0.3223(3) -0.2246(3) 0.0838(10) Uani 1 1 d . . . H28 H 0.6265 -0.3392 -0.3034 0.101 Uiso 1 1 calc R . . C29 C 0.6204(4) -0.4138(3) -0.1795(4) 0.0933(12) Uani 1 1 d . . . H29 H 0.5887 -0.4928 -0.2269 0.112 Uiso 1 1 calc R . . C30 C 0.6425(4) -0.3902(3) -0.0653(4) 0.0867(11) Uani 1 1 d . . . H30 H 0.6240 -0.4531 -0.0346 0.104 Uiso 1 1 calc R . . C31 C 0.6927(3) -0.2728(3) 0.0058(3) 0.0691(9) Uani 1 1 d . . . H31 H 0.7089 -0.2575 0.0844 0.083 Uiso 1 1 calc R . . C32 C 0.8872(3) -0.0306(2) 0.1536(2) 0.0473(6) Uani 1 1 d . . . C33 C 1.0078(3) -0.0679(2) 0.1571(2) 0.0567(7) Uani 1 1 d . . . H33 H 1.0179 -0.1071 0.0888 0.068 Uiso 1 1 calc R . . C34 C 1.1120(3) -0.0471(3) 0.2608(3) 0.0681(8) Uani 1 1 d . . . H34 H 1.1929 -0.0710 0.2620 0.082 Uiso 1 1 calc R . . C35 C 1.0977(4) 0.0083(3) 0.3617(3) 0.0764(10) Uani 1 1 d . . . H35 H 1.1687 0.0224 0.4314 0.092 Uiso 1 1 calc R . . C36 C 0.9778(4) 0.0433(3) 0.3601(3) 0.0760(9) Uani 1 1 d . . . H36 H 0.9673 0.0800 0.4290 0.091 Uiso 1 1 calc R . . C37 C 0.8728(3) 0.0241(2) 0.2567(2) 0.0603(8) Uani 1 1 d . . . H37 H 0.7921 0.0480 0.2564 0.072 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 N1 0.0696(17) 0.0436(14) 0.0810(17) 0.0169(12) 0.0356(14) 0.0112(12) N2 0.0604(17) 0.0710(17) 0.0672(17) 0.0241(13) 0.0114(14) 0.0144(13) C1 0.074(2) 0.0433(16) 0.0550(17) 0.0091(13) 0.0156(15) 0.0128(15) C2 0.112(3) 0.068(2) 0.085(2) 0.0275(18) 0.050(2) 0.041(2) C3 0.106(3) 0.087(3) 0.083(3) 0.017(2) 0.045(2) 0.029(2) C4 0.109(3) 0.088(3) 0.102(3) 0.000(2) 0.043(3) 0.046(3) C5 0.112(3) 0.063(2) 0.101(3) 0.020(2) 0.027(3) 0.038(2) C6 0.083(2) 0.0521(18) 0.070(2) 0.0162(15) 0.0174(18) 0.0230(17) C7 0.087(2) 0.0458(17) 0.073(2) 0.0181(16) 0.0318(19) 0.0245(17) C8 0.093(3) 0.0598(19) 0.0550(19) 0.0161(15) 0.0337(17) 0.0121(18) C9 0.094(3) 0.059(2) 0.071(2) 0.0219(17) 0.033(2) 0.0107(19) C10 0.092(3) 0.0553(19) 0.119(3) 0.041(2) 0.055(2) 0.0232(19) C11 0.066(2) 0.0428(16) 0.076(2) 0.0142(15) 0.0158(18) 0.0172(15) C12 0.087(3) 0.080(3) 0.111(3) 0.019(2) 0.019(3) 0.032(2) C13 0.104(3) 0.090(3) 0.095(3) 0.017(2) 0.008(3) 0.032(3) C14 0.103(3) 0.080(2) 0.075(2) 0.021(2) 0.023(2) 0.035(2) C15 0.113(3) 0.068(2) 0.056(2) 0.0163(17) 0.019(2) 0.041(2) C16 0.078(2) 0.0416(16) 0.074(2) 0.0206(15) 0.0189(18) 0.0256(16) C17 0.0611(19) 0.0409(15) 0.0661(18) 0.0177(13) 0.0285(15) 0.0143(14) C18 0.0560(18) 0.0487(16) 0.0709(19) 0.0212(14) 0.0310(15) 0.0237(14) C19 0.0426(15) 0.0488(16) 0.0642(18) 0.0185(13) 0.0235(13) 0.0149(13) C20 0.0481(16) 0.0426(14) 0.0524(16) 0.0185(12) 0.0212(13) 0.0149(13) C21 0.0485(17) 0.0508(17) 0.0717(19) 0.0218(14) 0.0253(15) 0.0197(14) C22 0.0434(16) 0.0502(17) 0.076(2) 0.0171(15) 0.0186(14) 0.0117(13) C23 0.0405(15) 0.0463(15) 0.0491(15) 0.0173(12) 0.0196(12) 0.0127(12) C24 0.0502(17) 0.0441(15) 0.0612(18) 0.0208(13) 0.0263(16) 0.0150(13) C25 0.0436(15) 0.0481(15) 0.0541(16) 0.0191(12) 0.0257(13) 0.0180(12) C26 0.0446(16) 0.0435(15) 0.0590(18) 0.0112(13) 0.0184(13) 0.0153(12) C27 0.0625(19) 0.0622(19) 0.064(2) 0.0105(15) 0.0262(15) 0.0215(15) C28 0.078(2) 0.078(2) 0.075(2) -0.006(2) 0.0195(19) 0.0241(19) C29 0.078(3) 0.059(2) 0.113(3) -0.004(2) 0.015(2) 0.0177(19) C30 0.077(2) 0.0461(19) 0.119(3) 0.020(2) 0.018(2) 0.0099(17) C31 0.069(2) 0.0558(19) 0.078(2) 0.0236(16) 0.0178(17) 0.0179(16) C32 0.0526(17) 0.0414(14) 0.0517(16) 0.0164(12) 0.0200(13) 0.0170(12) C33 0.0581(18) 0.0526(16) 0.0653(19) 0.0184(14) 0.0245(15) 0.0237(14) C34 0.0594(19) 0.067(2) 0.082(2) 0.0325(17) 0.0161(18) 0.0272(16) C35 0.077(2) 0.078(2) 0.064(2) 0.0268(18) 0.0035(18) 0.0245(19) C36 0.095(3) 0.079(2) 0.0516(19) 0.0178(16) 0.0209(18) 0.031(2) C37 0.067(2) 0.0617(18) 0.0574(19) 0.0175(14) 0.0246(16) 0.0271(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.414(4) . ? N1 C17 1.416(3) . ? N1 C7 1.468(4) . ? N2 C24 1.144(3) . ? C1 C6 1.368(4) . ? C1 C2 1.389(4) . ? C2 C3 1.363(5) . ? C3 C4 1.385(5) . ? C4 C5 1.367(5) . ? C5 C6 1.366(5) . ? C7 C8 1.361(4) . ? C7 C16 1.371(4) . ? C8 C9 1.373(4) . ? C9 C10 1.392(5) . ? C10 C11 1.442(5) . ? C11 C12 1.394(5) . ? C11 C16 1.422(4) . ? C12 C13 1.341(5) . ? C13 C14 1.402(5) . ? C14 C15 1.342(5) . ? C15 C16 1.458(4) . ? C17 C18 1.387(4) . ? C17 C22 1.388(4) . ? C18 C19 1.379(4) . ? C19 C20 1.393(3) . ? C20 C21 1.391(4) . ? C20 C23 1.491(3) . ? C21 C22 1.373(4) . ? C23 C25 1.354(3) . ? C23 C24 1.437(4) . ? C25 C32 1.488(3) . ? C25 C26 1.494(3) . ? C26 C27 1.382(4) . ? C26 C31 1.392(4) . ? C27 C28 1.382(4) . ? C28 C29 1.353(5) . ? C29 C30 1.353(5) . ? C30 C31 1.382(4) . ? C32 C37 1.384(4) . ? C32 C33 1.393(4) . ? C33 C34 1.377(4) . ? C34 C35 1.362(4) . ? C35 C36 1.375(4) . ? C36 C37 1.381(4) . ? 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 C1 N1 C17 119.8(2) . . ? C1 N1 C7 121.1(2) . . ? C17 N1 C7 117.0(2) . . ? C6 C1 C2 118.6(3) . . ? C6 C1 N1 122.0(3) . . ? C2 C1 N1 119.4(3) . . ? C3 C2 C1 121.4(3) . . ? C2 C3 C4 119.6(4) . . ? C5 C4 C3 118.7(4) . . ? C6 C5 C4 121.9(3) . . ? C5 C6 C1 119.9(3) . . ? C8 C7 C16 119.8(3) . . ? C8 C7 N1 120.7(3) . . ? C16 C7 N1 119.5(3) . . ? C7 C8 C9 123.5(3) . . ? C8 C9 C10 119.1(3) . . ? C9 C10 C11 118.9(3) . . ? C12 C11 C16 119.9(3) . . ? C12 C11 C10 121.2(4) . . ? C16 C11 C10 118.8(3) . . ? C13 C12 C11 121.3(4) . . ? C12 C13 C14 119.8(4) . . ? C15 C14 C13 122.6(4) . . ? C14 C15 C16 118.9(4) . . ? C7 C16 C11 119.9(3) . . ? C7 C16 C15 122.7(3) . . ? C11 C16 C15 117.4(3) . . ? C18 C17 C22 118.6(2) . . ? C18 C17 N1 121.1(3) . . ? C22 C17 N1 120.2(3) . . ? C19 C18 C17 120.2(3) . . ? C18 C19 C20 121.8(3) . . ? C21 C20 C19 117.1(2) . . ? C21 C20 C23 122.8(2) . . ? C19 C20 C23 120.0(2) . . ? C22 C21 C20 121.5(2) . . ? C21 C22 C17 120.7(3) . . ? C25 C23 C24 120.1(2) . . ? C25 C23 C20 127.0(2) . . ? C24 C23 C20 112.8(2) . . ? N2 C24 C23 175.5(3) . . ? C23 C25 C32 121.3(2) . . ? C23 C25 C26 123.2(2) . . ? C32 C25 C26 115.5(2) . . ? C27 C26 C31 117.6(3) . . ? C27 C26 C25 122.9(2) . . ? C31 C26 C25 119.5(3) . . ? C26 C27 C28 120.3(3) . . ? C29 C28 C27 121.1(4) . . ? C28 C29 C30 119.9(3) . . ? C29 C30 C31 120.2(3) . . ? C30 C31 C26 120.9(3) . . ? C37 C32 C33 118.4(2) . . ? C37 C32 C25 121.3(2) . . ? C33 C32 C25 120.3(2) . . ? C34 C33 C32 120.4(3) . . ? C35 C34 C33 120.6(3) . . ? C34 C35 C36 119.8(3) . . ? C35 C36 C37 120.4(3) . . ? C36 C37 C32 120.4(3) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.456 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.040