#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/49/2004929.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2004929 loop_ _publ_author_name 'Morales, G. A.' 'Fronczek, F. R.' _publ_section_title ; A Kryptoracemic Hydroperoxide ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1266 _journal_page_last 1268 _journal_volume 52 _journal_year 1996 _chemical_formula_moiety 'C16 H19 N1 O2 Si1' _chemical_formula_sum 'C16 H19 N O2 Si' _chemical_formula_weight 285.42 _chemical_name_systematic ; 2-(trimethylsilyl)-3-methyl-3H-benz[f]indolyl-3-hydroperoxide ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2y1' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_type_scat_source IntTabIV _cell_angle_alpha 90 _cell_angle_beta 96.40(1) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.734(1) _cell_length_b 17.075(1) _cell_length_c 9.764(1) _cell_measurement_reflns_used 25 _cell_measurement_temperature 295 _cell_measurement_theta_max 25 _cell_measurement_theta_min 20 _cell_volume 1612.7(3) _computing_cell_refinement CAD-4 _computing_data_collection 'CAD-4 (Enraf-Nonius, 1977)' _computing_data_reduction 'PROCESS MolEN (Fair, 1990)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'CIF IN MolEN' _computing_structure_refinement 'LSFM MolEN' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_measurement_device Enraf_Nonius_CAD4 _diffrn_measurement_method \q/2\q _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.021 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 6931 _diffrn_reflns_theta_max 74.88 _diffrn_standards_decay_% -5.4 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 1.28 _exptl_absorpt_correction_T_max 0.9978 _exptl_absorpt_correction_T_min 0.8942 _exptl_absorpt_correction_type \y_scans_(North,_Phillips_&_Mathews,_1968) _exptl_crystal_colour Golden_yellow _exptl_crystal_density_diffrn 1.176 _exptl_crystal_description prism _exptl_crystal_F_000 608 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.23 _refine_diff_density_max 0.39 _refine_diff_density_min -0.11 _refine_ls_abs_structure_details ; The structure with the opposite direction of the polar axis was refined under identical circumstances, yielding R=0.046, wR=0.054, S=2.433. The better refinement is reported. ; _refine_ls_extinction_coef 0.17E-05(2) _refine_ls_extinction_method isotropic_(Zachariasen,_1963) _refine_ls_goodness_of_fit_obs 2.146 _refine_ls_hydrogen_treatment 'H atoms: see text' _refine_ls_number_parameters 369 _refine_ls_number_reflns 5807 _refine_ls_R_factor_obs 0.041 _refine_ls_shift/esd_max 0.020 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme '4Fo^2^/[\s^2^(Fo^2^) + 0.0004 Fo^4^]' _refine_ls_wR_factor_obs 0.048 _reflns_number_observed 5807 _reflns_number_total 6562 _reflns_observed_criterion >3.0\s(I) _[local]_cod_data_source_file ta1061.cif _[local]_cod_data_source_block 1 _[local]_cod_cif_authors_sg_H-M 'P 21' _[local]_cod_chemical_formula_sum_orig 'C16 H19 N1 O2 Si1' _cod_original_cell_volume 1612.8(4) _cod_database_code 2004929 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag Si1A 0.57600(6) 1 0.23086(7) 0.0546(2) Uani ? O1A 0.5467(2) 0.88827(9) -0.0659(1) 0.0516(4) Uani ? O2A 0.4903(2) 0.9637(1) -0.1125(2) 0.0619(5) Uani ? N1A 0.3159(2) 0.9352(1) 0.1602(2) 0.0453(4) Uani ? C1A 0.4455(2) 0.9287(1) 0.1430(2) 0.0434(5) Uani ? C2A 0.4719(2) 0.8621(1) 0.0434(2) 0.0432(5) Uani ? C3A 0.3257(2) 0.8358(1) -0.0022(2) 0.0418(5) Uani ? C4A 0.2380(2) 0.8807(1) 0.0729(2) 0.0416(5) Uani ? C5A 0.2733(2) 0.7797(1) -0.0903(2) 0.0504(6) Uani ? C6A 0.1274(2) 0.7669(1) -0.1106(2) 0.0508(6) Uani ? C7A 0.0668(3) 0.7091(2) -0.2016(3) 0.0699(8) Uani ? C8A -0.0731(3) 0.6967(2) -0.2171(3) 0.0782(9) Uani ? C9A -0.1584(3) 0.7438(2) -0.1467(3) 0.0772(8) Uani ? C10A -0.1040(2) 0.8008(2) -0.0596(3) 0.0646(7) Uani ? C11A 0.0402(2) 0.8135(1) -0.0362(2) 0.0495(6) Uani ? C12A 0.0982(2) 0.8712(1) 0.0569(2) 0.0482(5) Uani ? C13A 0.5616(2) 0.7977(2) 0.1134(3) 0.0606(7) Uani ? C14A 0.7462(3) 0.9897(2) 0.1629(3) 0.095(1) Uani ? C15A 0.5003(4) 1.0978(2) 0.1922(3) 0.084(1) Uani ? C16A 0.5919(3) 0.9785(2) 0.4173(3) 0.0747(9) Uani ? Si1B 0.08680(8) 1.04709(5) 0.72225(7) 0.0705(2) Uani ? O1B 0.0701(2) 0.9705(1) 0.3884(2) 0.0640(5) Uani ? O2B 0.1987(2) 1.0127(1) 0.3733(2) 0.0598(4) Uani ? N1B 0.2843(2) 0.9318(1) 0.6767(2) 0.0525(5) Uani ? C1B 0.1647(2) 0.9609(1) 0.6334(2) 0.0540(6) Uani ? C2B 0.0965(2) 0.9179(2) 0.5038(2) 0.0549(6) Uani ? C3B 0.2041(2) 0.8573(1) 0.4832(2) 0.0494(5) Uani ? C4B 0.3133(2) 0.8681(1) 0.5884(2) 0.0481(5) Uani ? C5B 0.2068(2) 0.7987(1) 0.3906(2) 0.0548(6) Uani ? C6B 0.3227(2) 0.7479(1) 0.3982(2) 0.0540(6) Uani ? C7B 0.3288(3) 0.6839(2) 0.3064(3) 0.0708(8) Uani ? C8B 0.4391(3) 0.6347(2) 0.3172(3) 0.0820(9) Uani ? C9B 0.5491(3) 0.6481(2) 0.4160(3) 0.0821(8) Uani ? C10B 0.5496(3) 0.7092(2) 0.5057(3) 0.0721(8) Uani ? C11B 0.4348(2) 0.7606(1) 0.5012(2) 0.0539(6) Uani ? C12B 0.4278(2) 0.8223(1) 0.5983(2) 0.0544(6) Uani ? C13B -0.0440(3) 0.8831(2) 0.5204(3) 0.084(1) Uani ? C14B 0.0369(4) 1.1226(2) 0.5914(3) 0.111(1) Uani ? C15B -0.0687(3) 1.0143(3) 0.7989(3) 0.107(1) Uani ? C16B 0.2150(4) 1.0829(2) 0.8614(3) 0.096(1) Uani ? H2OA 0.408(3) 0.950(2) -0.169(3) 0.10(1) Uiso ? H2OB 0.223(3) 0.979(2) 0.303(3) 0.12(1) Uiso ? H5A 0.3331 0.7488 -0.1386 0.0656 Uiso calc H7A 0.1241 0.6782 -0.2529 0.0908 Uiso calc H8A -0.1117 0.6561 -0.2757 0.1017 Uiso calc H9A -0.2556 0.7360 -0.1596 0.1004 Uiso calc H10A -0.1642 0.8328 -0.0135 0.0840 Uiso calc H12A 0.0409 0.9027 0.1072 0.0627 Uiso calc H131A 0.5184 0.7770 0.1882 0.0787 Uiso calc H132A 0.5731 0.7572 0.0489 0.0787 Uiso calc H133A 0.6494 0.8186 0.1468 0.0787 Uiso calc H141A 0.8099 1.0260 0.2083 0.1235 Uiso calc H142A 0.7799 0.9379 0.1790 0.1235 Uiso calc H143A 0.7357 1.0000 0.0667 0.1235 Uiso calc H151A 0.5609 1.1369 0.2335 0.1088 Uiso calc H152A 0.4875 1.1055 0.0952 0.1088 Uiso calc H153A 0.4137 1.1014 0.2279 0.1088 Uiso calc H161A 0.6568 1.0134 0.4647 0.0971 Uiso calc H162A 0.5045 0.9850 0.4505 0.0971 Uiso calc H163A 0.6225 0.9261 0.4327 0.0971 Uiso calc H5B 0.1317 0.7916 0.3208 0.0712 Uiso calc H7B 0.2545 0.6754 0.2363 0.0921 Uiso calc H8B 0.4405 0.5912 0.2567 0.1066 Uiso calc H9B 0.6264 0.6138 0.4218 0.1067 Uiso calc H10B 0.6276 0.7176 0.5717 0.0937 Uiso calc H12B 0.5018 0.8311 0.6686 0.0707 Uiso calc H131B -0.0357 0.8473 0.5953 0.1089 Uiso calc H132B -0.1063 0.9238 0.5380 0.1089 Uiso calc H133B -0.0782 0.8564 0.4383 0.1089 Uiso calc H141B -0.0022 1.1661 0.6337 0.1440 Uiso calc H142B 0.1163 1.1391 0.5508 0.1440 Uiso calc H143B -0.0292 1.1015 0.5222 0.1440 Uiso calc H151B -0.1074 1.0573 0.8430 0.1389 Uiso calc H152B -0.1348 0.9945 0.7284 0.1389 Uiso calc H153B -0.0440 0.9742 0.8645 0.1389 Uiso calc H161B 0.1774 1.1259 0.9065 0.1252 Uiso calc H162B 0.2376 1.0420 0.9260 0.1252 Uiso calc H163B 0.2960 1.0992 0.8235 0.1252 Uiso calc loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Si1A 0.0473(3) 0.0621(3) 0.0549(3) -0.0109(3) 0.0073(2) -0.0085(3) O1A 0.0496(7) 0.0580(8) 0.0500(7) 0.0013(7) 0.0186(6) 0.0058(7) O2A 0.0750(10) 0.0549(9) 0.0556(9) -0.0068(8) 0.0083(8) 0.0092(8) N1A 0.0425(8) 0.0524(9) 0.0419(8) -0.0022(8) 0.0083(7) -0.0072(8) C1A 0.0394(9) 0.0510(10) 0.0397(9) -0.0008(9) 0.0061(8) 0.0002(9) C2A 0.0403(9) 0.0460(10) 0.0450(10) 0.0007(8) 0.0109(8) 0.0020(9) C3A 0.0430(9) 0.0410(10) 0.0430(10) 0.0010(8) 0.0124(8) -0.0002(9) C4A 0.0432(9) 0.0420(10) 0.0406(9) 0.0001(8) 0.0100(8) -0.0044(9) C5A 0.0530(10) 0.0460(10) 0.0550(10) 0.0020(9) 0.0162(9) -0.0080(10) C6A 0.0560(10) 0.0490(10) 0.0480(10) -0.0060(10) 0.0080(10) -0.0050(10) C7A 0.076(2) 0.0640(10) 0.070(2) -0.0130(10) 0.0100(10) -0.0210(10) C8A 0.081(2) 0.077(2) 0.075(2) -0.0300(10) 0.0020(10) -0.0220(10) C9A 0.0590(10) 0.102(2) 0.071(2) -0.0280(10) 0.0060(10) -0.014(2) C10A 0.0500(10) 0.083(2) 0.0620(10) -0.0140(10) 0.0080(10) -0.0120(10) C11A 0.0480(10) 0.0550(10) 0.0460(10) -0.0060(10) 0.0082(9) -0.0030(10) C12A 0.0420(10) 0.0560(10) 0.0480(10) -0.0007(9) 0.0095(8) -0.0090(10) C13A 0.0500(10) 0.0600(10) 0.0730(10) 0.0070(10) 0.0130(10) 0.0150(10) C14A 0.0580(10) 0.133(3) 0.098(2) -0.030(2) 0.0230(10) -0.033(2) C15A 0.107(2) 0.062(2) 0.083(2) -0.0210(10) 0.014(2) -0.003(2) C16A 0.067(2) 0.094(2) 0.061(2) -0.0020(10) 0.0000(10) -0.011(2) Si1B 0.0852(4) 0.0711(4) 0.0604(3) 0.0347(3) 0.0318(3) 0.0144(3) O1B 0.0547(8) 0.0780(10) 0.0591(9) 0.0191(8) 0.0051(7) 0.0155(8) O2B 0.0743(9) 0.0564(9) 0.0513(8) 0.0057(8) 0.0184(7) 0.0009(8) N1B 0.0550(10) 0.0600(10) 0.0438(9) 0.0143(9) 0.0101(8) 0.0055(9) C1B 0.0550(10) 0.0600(10) 0.0490(10) 0.0160(10) 0.0158(9) 0.0110(10) C2B 0.0460(10) 0.0620(10) 0.0570(10) 0.0100(10) 0.0080(10) 0.0110(10) C3B 0.0470(10) 0.0500(10) 0.0520(10) 0.0031(9) 0.0071(9) 0.0090(10) C4B 0.0480(10) 0.0510(10) 0.0470(10) 0.0097(9) 0.0105(9) 0.0050(10) C5B 0.0570(10) 0.0540(10) 0.0540(10) -0.0060(10) 0.0060(10) 0.0070(10) C6B 0.0660(10) 0.0440(10) 0.0550(10) -0.0030(10) 0.0220(10) 0.0070(10) C7B 0.089(2) 0.0520(10) 0.076(2) -0.0120(10) 0.0280(10) -0.0030(10) C8B 0.112(2) 0.0520(10) 0.090(2) 0.0020(10) 0.0460(10) -0.0050(10) C9B 0.102(2) 0.0590(10) 0.094(2) 0.0250(10) 0.0510(10) 0.0110(10) C10B 0.0760(10) 0.072(2) 0.072(2) 0.0250(10) 0.0270(10) 0.0180(10) C11B 0.0580(10) 0.0520(10) 0.0550(10) 0.0100(10) 0.0210(10) 0.0100(10) C12B 0.0500(10) 0.0650(10) 0.0490(10) 0.0140(10) 0.0094(9) 0.0080(10) C13B 0.0480(10) 0.106(2) 0.098(2) 0.0020(10) 0.0150(10) 0.015(2) C14B 0.149(2) 0.097(2) 0.097(2) 0.068(2) 0.061(2) 0.040(2) C15B 0.100(2) 0.135(3) 0.095(2) 0.049(2) 0.0530(10) 0.033(2) C16B 0.127(2) 0.087(2) 0.080(2) 0.024(2) 0.031(2) -0.016(2) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C1A Si1A C14A 110.90(10) yes C1A Si1A C15A 104.90(10) yes C1A Si1A C16A 107.30(10) yes C14A Si1A C15A 111.3(2) yes C14A Si1A C16A 110.70(10) yes C15A Si1A C16A 111.60(10) yes O2A O1A C2A 107.70(10) yes O1A O2A H2OA 103.0(10) yes C1A N1A C4A 109.2(2) yes Si1A C1A N1A 120.0(2) yes Si1A C1A C2A 127.70(10) yes N1A C1A C2A 112.2(2) yes O1A C2A C1A 112.1(2) yes O1A C2A C3A 114.5(2) yes O1A C2A C13A 104.3(2) yes C1A C2A C3A 100.9(2) yes C1A C2A C13A 112.3(2) yes C3A C2A C13A 113.1(2) yes C2A C3A C4A 106.9(2) yes C2A C3A C5A 132.5(2) yes C4A C3A C5A 120.6(2) yes N1A C4A C3A 110.7(2) yes N1A C4A C12A 127.2(2) yes C3A C4A C12A 122.1(2) yes C3A C5A C6A 119.8(2) yes C5A C6A C7A 122.2(2) yes C5A C6A C11A 119.0(2) yes C7A C6A C11A 118.8(2) yes C6A C7A C8A 121.1(3) yes C7A C8A C9A 119.9(3) yes C8A C9A C10A 120.7(2) yes C9A C10A C11A 121.4(2) yes C6A C11A C10A 118.1(2) yes C6A C11A C12A 120.0(2) yes C10A C11A C12A 121.9(2) yes C4A C12A C11A 118.6(2) yes C1B Si1B C14B 108.20(10) yes C1B Si1B C15B 109.6(2) yes C1B Si1B C16B 108.70(10) yes C14B Si1B C15B 109.2(2) yes C14B Si1B C16B 112.6(2) yes C15B Si1B C16B 108.7(2) yes O2B O1B C2B 107.80(10) yes O1B O2B H2OB 93.0(10) yes C1B N1B C4B 108.9(2) yes Si1B C1B N1B 122.4(2) yes Si1B C1B C2B 125.6(2) yes N1B C1B C2B 112.0(2) yes O1B C2B C1B 111.5(2) yes O1B C2B C3B 113.0(2) yes O1B C2B C13B 104.1(2) yes C1B C2B C3B 101.2(2) yes C1B C2B C13B 114.1(2) yes C3B C2B C13B 113.3(2) yes C2B C3B C4B 107.1(2) yes C2B C3B C5B 131.8(2) yes C4B C3B C5B 121.1(2) yes N1B C4B C3B 110.8(2) yes N1B C4B C12B 127.5(2) yes C3B C4B C12B 121.6(2) yes C3B C5B C6B 119.5(2) yes C5B C6B C7B 121.8(2) yes C5B C6B C11B 119.3(2) yes C7B C6B C11B 118.9(2) yes C6B C7B C8B 121.0(2) yes C7B C8B C9B 119.9(3) yes C8B C9B C10B 121.6(3) yes C9B C10B C11B 120.5(2) yes C6B C11B C10B 118.0(2) yes C6B C11B C12B 119.8(2) yes C10B C11B C12B 122.2(2) yes C4B C12B C11B 118.6(2) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Si1A C1A 1.894(2) yes Si1A C14A 1.861(3) yes Si1A C15A 1.847(3) yes Si1A C16A 1.847(3) yes O1A O2A 1.453(2) yes O1A C2A 1.430(3) yes O2A H2OA 0.95(3) yes N1A C1A 1.296(3) yes N1A C4A 1.423(3) yes C1A C2A 1.536(3) yes C2A C3A 1.511(3) yes C2A C13A 1.518(3) yes C3A C4A 1.411(3) yes C3A C5A 1.350(3) yes C4A C12A 1.361(3) yes C5A C6A 1.428(3) yes C6A C7A 1.413(3) yes C6A C11A 1.421(3) yes C7A C8A 1.369(4) yes C8A C9A 1.391(4) yes C9A C10A 1.361(4) yes C10A C11A 1.413(3) yes C11A C12A 1.415(3) yes Si1B C1B 1.909(3) yes Si1B C14B 1.841(3) yes Si1B C15B 1.849(4) yes Si1B C16B 1.844(3) yes O1B O2B 1.465(3) yes O1B C2B 1.442(3) yes O2B H2OB 0.95(3) yes N1B C1B 1.293(3) yes N1B C4B 1.435(3) yes C1B C2B 1.547(3) yes C2B C3B 1.502(3) yes C2B C13B 1.516(4) yes C3B C4B 1.406(3) yes C3B C5B 1.351(3) yes C4B C12B 1.357(3) yes C5B C6B 1.419(3) yes C6B C7B 1.418(4) yes C6B C11B 1.415(3) yes C7B C8B 1.359(4) yes C8B C9B 1.378(4) yes C9B C10B 1.362(4) yes C10B C11B 1.418(4) yes C11B C12B 1.424(3) yes