#------------------------------------------------------------------------------ #$Date: 2012-01-04 10:35:04 +0000 (Wed, 04 Jan 2012) $ #$Revision: 31985 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/06/2000648.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_2000648 loop_ _publ_author_name 'Ianelli, S.' 'Nardelli, M.' 'Belletti, D.' 'Jamart-Gr\'egoire, B.' 'Forconi, H.' 'Caub\`ere, P.' _publ_contact_author ; Prof. Mario Nardelli Istituto di Chimica Generale ed Inorganica Universit\`a degli Studi di Parma Viale delle Scienze 78 I-43100 Parma Italy ; _publ_section_title ; Structure and conformation of 1'-phenylindan-2-spiro-4'-piperidin-1-one ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1727 _journal_page_last 1730 _journal_volume 48 _journal_year 1992 _chemical_formula_analytical ' C19 H19 N O ' _chemical_formula_moiety ' C19 H19 N O ' _chemical_formula_sum 'C19 H19 N O' _[local]_cod_chemical_formula_sum_orig ' C19 H19 N O ' _chemical_formula_weight 277.36 _chemical_name_systematic ; 1-Indanone-2-spiro-4'-N-phenylpiperidine ; _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _cell_angle_alpha 90.00(0.00) _cell_angle_beta 90.00(0.00) _cell_angle_gamma 90.00(0.00) _cell_formula_units_Z 8 _cell_length_a 29.018(3) _cell_length_b 8.5300(10) _cell_length_c 11.7620(10) _cell_measurement_reflns_used 30 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 37 _cell_measurement_theta_min 15 _cell_volume 2911(5) _computing_cell_refinement 'LQPARM (Nardelli & Mangia, 1984)' _computing_molecular_graphics 'ORTEP (Johnson, 1965)' _computing_publication_material 'PARST (Nardelli, 1983)' _computing_structure_refinement 'SHELX76 (Sheldrick, 1976)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1986)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Siemens--AED diffractometer' _diffrn_measurement_method \q--2\q _diffrn_radiation_monochromator 'nickel filter' _diffrn_radiation_source 'standard Cu anode' _diffrn_radiation_type 'X-ray Cu K-\a mean' _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3205 _diffrn_reflns_reduction_process ; Standard. Lp correction. ; _diffrn_reflns_theta_max 70 _diffrn_reflns_theta_min 3 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 50 _diffrn_standards_number 1 _exptl_absorpt_coefficient_mu .569 _exptl_absorpt_correction_type 'not applied' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.266 _exptl_crystal_description ; Thin prisms ; _exptl_crystal_F_000 1184.0 _exptl_crystal_size_max 0.77 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.09 _refine_diff_density_min -0.10 _refine_ls_goodness_of_fit_obs 0.8064 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 266 _refine_ls_number_reflns 1829 _refine_ls_number_restraints 0 _refine_ls_R_factor_obs 0.0395 _refine_ls_shift/esd_max 0.09 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme w=1/[\s^2^(F~o~)+0.003883F~o~^2^] _refine_ls_wR_factor_obs 0.0566 _reflns_observed_criterion I>3\s(I) _[local]_cod_data_source_file ka1005.cif _[local]_cod_data_source_block 3 _[local]_cod_cif_authors_sg_H-M 'P b c a ' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 13 2 3 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H Hydrogen .000 .000 'IT.4 Tab.2.2C ' 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 _atom_site_calc_attached_atom _atom_site_type_symbol O .42628(6) .3651(2) .99350(10) .0682(6) Uani . . O N .31783(5) .0629(2) .79970(10) .0430(5) Uani . . N C1 .41793(6) .4060(2) .8967(2) .0436(6) Uani . . C C2 .38472(6) .3223(2) .8159(2) .0401(5) Uani . . C C3 .38866(7) .4148(2) .7023(2) .0467(6) Uani . . C C4 .43274(7) .6737(2) .6578(2) .0501(7) Uani . . C C5 .46151(8) .7885(3) .7009(2) .0583(7) Uani . . C C6 .47866(8) .7807(3) .8107(2) .0572(7) Uani . . C C7 .46661(7) .6581(2) .8805(2) .0481(7) Uani . . C C8 .43686(6) .5446(2) .8388(2) .0381(6) Uani . . C C9 .41973(6) .5511(2) .7285(2) .0391(5) Uani . . C C10 .39885(7) .1499(2) .8030(2) .0455(6) Uani . . C C11 .36234(8) .0561(3) .7406(2) .0481(7) Uani . . C C12 .30227(7) .2264(2) .8024(2) .0458(6) Uani . . C C13 .33579(7) .3307(2) .8666(2) .0439(6) Uani . . C C14 .31252(6) -.0279(2) .8989(2) .0395(5) Uani . . C C15 .33727(7) -.1663(2) .9146(2) .0491(7) Uani . . C C16 .33050(8) -.2581(3) 1.0107(2) .0530(7) Uani . . C C17 .29947(8) -.2162(3) 1.0936(2) .0552(7) Uani . . C C18 .27443(8) -.0810(3) 1.0784(2) .0567(7) Uani . . C C19 .28044(7) .0121(3) .9832(2) .0505(6) Uani . . C H31 .3568(8) .459(3) .6777(19) .056(6) Uiso . C3 H H32 .4032(8) .351(3) .634(2) .061(6) Uiso . C3 H H4 .4208(8) .678(3) .572(2) .075(8) Uiso . C4 H H5 .4689(8) .878(3) .6515(19) .057(6) Uiso . C5 H H6 .4992(9) .860(3) .834(2) .073(8) Uiso . C6 H H7 .4770(8) .650(3) .951(2) .066(7) Uiso . C7 H H101 .4033(7) .108(3) .8850(19) .051(6) Uiso . C10 H H102 .4313(9) .146(3) .765(2) .063(7) Uiso . C10 H H111 .3689(8) -.056(3) .7315(18) .053(6) Uiso . C11 H H112 .3573(7) .104(3) .6665(19) .046(6) Uiso . C11 H H121 .3008(7) .256(3) .7192(18) .047(5) Uiso . C12 H H122 .2708(7) .226(3) .8383(17) .048(6) Uiso . C12 H H131 .3373(7) .299(2) .9454(18) .046(5) Uiso . C13 H H132 .3254(7) .439(3) .8570(18) .049(6) Uiso . C13 H H15 .3602(8) -.199(3) .861(2) .061(7) Uiso . C15 H H16 .3509(8) -.348(3) 1.022(2) .069(7) Uiso . C16 H H17 .2955(8) -.285(3) 1.1638(19) .059(6) Uiso . C17 H H18 .2522(10) -.047(3) 1.132(2) .081(8) Uiso . C18 H H19 .2613(7) .110(3) .9779(17) .054(6) Uiso . C19 H 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 O .0817(11) .0769(12) .0461(8) .0165(8) -.0183(7) -.0248(9) N .0441(9) .0385(9) .0465(8) -.0038(7) -.0006(7) -.0010(7) C1 .0450(10) .0469(11) .0388(10) .0012(8) -.0041(8) -.0025(9) C2 .0429(9) .0374(9) .0400(9) .0005(7) -.0026(7) -.0001(8) C3 .0548(11) .0445(11) .0410(10) .0025(8) -.0079(9) -.0064(9) C4 .0524(11) .0476(12) .0503(11) .0071(9) .0018(9) -.0024(9) C5 .0590(13) .0529(13) .0630(13) .0076(11) .0088(10) -.0092(11) C6 .0514(11) .0523(13) .0678(14) -.0080(11) .0061(10) -.0132(10) C7 .0420(10) .0541(13) .0483(11) -.0093(9) -.0016(9) -.0051(9) C8 .0354(8) .0389(10) .0399(9) -.0030(7) .0012(7) .0036(7) C9 .0396(9) .0374(10) .0402(9) -.0014(7) .0007(7) .0038(7) C10 .0414(10) .0428(11) .0523(11) .0020(9) .0075(9) .0028(8) C11 .0584(13) .0401(11) .0458(11) -.0059(9) .0078(9) -.0020(9) C12 .0419(10) .0415(11) .0542(11) .0013(9) -.0064(9) .0026(8) C13 .0452(11) .0366(11) .0500(11) -.0027(8) -.0014(8) .0027(8) C14 .0368(9) .0358(9) .0459(10) -.0054(8) -.0035(7) -.0059(7) C15 .0486(11) .0451(12) .0535(11) -.0054(9) .0006(9) .0034(9) C16 .0580(12) .0414(11) .0597(12) .0010(9) -.0059(10) -.0010(10) C17 .0627(13) .0485(12) .0544(11) .0034(10) .0007(10) -.0141(10) C18 .0534(12) .0554(13) .0613(13) -.0037(10) .0152(10) -.0105(10) C19 .0453(10) .0443(11) .0619(12) -.0012(10) .0076(9) .0003(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O C1 1.215(2) yes N C11 1.467(2) yes N C12 1.467(2) yes N C14 1.409(2) yes C1 C2 1.531(2) yes C1 C8 1.471(2) yes C2 C3 1.556(2) yes C2 C10 1.534(2) yes C2 C13 1.542(2) yes C3 C9 1.504(2) yes C3 H31 1.04(2) no C3 H32 1.05(2) no C4 C5 1.383(3) yes C4 C9 1.388(2) yes C4 H4 1.07(2) no C5 C6 1.386(3) yes C5 H5 .98(2) no C6 C7 1.375(3) yes C6 H6 .94(2) no C7 C8 1.387(2) yes C7 H7 .89(2) no C8 C9 1.390(2) yes C10 C11 1.516(3) yes C10 H101 1.04(2) no C10 H102 1.04(2) no C11 H111 .98(2) no C11 H112 .97(2) no C12 C13 1.519(2) yes C12 H121 1.01(2) no C12 H122 1.01(2) no C13 H131 .97(2) no C13 H132 .98(2) no C14 C15 1.395(2) yes C14 C19 1.402(2) yes C15 C16 1.390(3) yes C15 H15 .96(2) no C16 C17 1.375(3) yes C16 H16 .97(2) no C17 C18 1.375(3) yes C17 H17 1.02(2) no C18 C19 1.384(3) yes C18 H18 .95(2) no C19 H19 1.00(2) no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance O C2 2.440(2) O C8 2.398(2) N C2 2.950(2) N C10 2.466(2) N C13 2.472(2) N C15 2.443(2) N C19 2.454(2) C1 C3 2.441(2) C1 C7 2.580(2) C1 C9 2.334(2) C1 C10 2.509(2) C1 C13 2.494(2) C2 C8 2.441(2) C2 C9 2.429(2) C2 C11 2.521(2) C2 C12 2.533(2) C3 C4 2.605(2) C3 C8 2.401(2) C3 C10 2.568(2) C3 C13 2.569(2) C4 C6 2.418(3) C4 C7 2.801(3) C4 C8 2.400(2) C5 C7 2.392(3) C5 C8 2.733(3) C5 C9 2.382(3) C6 C8 2.374(2) C6 C9 2.774(2) C7 C9 2.425(2) C10 C12 2.878(2) C10 C13 2.508(2) C11 C12 2.382(3) C11 C13 2.876(2) C11 C14 2.464(2) C11 C15 2.884(3) C12 C14 2.466(2) C12 C19 2.875(3) C14 C16 2.421(2) C14 C17 2.822(2) C14 C18 2.426(2) C15 C17 2.412(3) C15 C18 2.751(3) C15 C19 2.385(2) C16 C18 2.359(3) C16 C19 2.744(3) C17 C19 2.405(3) 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 C12 N C14 118.1(2) yes C11 N C14 117.8(2) yes C11 N C12 108.6(2) yes O C1 C8 126.2(2) yes O C1 C2 125.0(2) yes C2 C1 C8 108.8(2) yes C1 C2 C13 108.5(2) yes C1 C2 C10 109.9(2) yes C1 C2 C3 104.5(2) yes C10 C2 C13 109.2(2) yes C3 C2 C13 112.1(2) yes C3 C2 C10 112.4(2) yes C2 C3 H32 115.0(10) no C2 C3 H31 111.0(10) no C2 C3 C9 105.1(2) yes H31 C3 H32 109(2) no C9 C3 H32 108.0(10) no C9 C3 H31 108.0(10) no C9 C4 H4 120.0(10) no C5 C4 H4 121.0(10) no C5 C4 C9 118.5(2) yes C4 C5 H5 118.0(10) no C4 C5 C6 121.6(2) yes C6 C5 H5 121.0(10) no C5 C6 H6 118(2) no C5 C6 C7 120.1(2) yes C7 C6 H6 122.0(10) no C6 C7 H7 122(2) no C6 C7 C8 118.6(2) yes C8 C7 H7 119(2) no C1 C8 C7 129.0(2) yes C7 C8 C9 121.7(2) yes C1 C8 C9 109.3(2) yes C4 C9 C8 119.5(2) yes C3 C9 C8 112.0(2) yes C3 C9 C4 128.5(2) yes C2 C10 H102 108.0(10) no C2 C10 H101 106.0(10) no C2 C10 C11 111.5(2) yes H101 C10 H102 106(2) no C11 C10 H102 114.0(10) no C11 C10 H101 111.0(10) no N C11 C10 111.4(2) yes C10 C11 H112 109.0(10) no C10 C11 H111 116.0(10) no N C11 H112 106.0(10) no N C11 H111 105.0(10) no H111 C11 H112 110(2) no N C12 H122 107.0(10) no N C12 H121 103.0(10) no N C12 C13 111.8(2) yes H121 C12 H122 112(2) no C13 C12 H122 112.0(10) no C13 C12 H121 111.0(10) no C2 C13 C12 111.7(2) yes C12 C13 H132 107.0(10) no C12 C13 H131 110.0(10) no C2 C13 H132 106.0(10) no C2 C13 H131 108.0(10) no H131 C13 H132 113(2) no N C14 C19 121.7(2) yes N C14 C15 121.2(2) yes C15 C14 C19 117.1(2) yes C14 C15 H15 121.0(10) no C14 C15 C16 120.8(2) yes C16 C15 H15 118.0(10) no C15 C16 H16 118.0(10) no C15 C16 C17 121.5(2) yes C17 C16 H16 120.0(10) no C16 C17 H17 120.0(10) no C16 C17 C18 118.2(2) yes C18 C17 H17 122.0(10) no C17 C18 H18 122(2) no C17 C18 C19 121.3(2) yes C19 C18 H18 117(2) no C14 C19 C18 121.1(2) yes C18 C19 H19 117.0(10) no C14 C19 H19 122.0(10) no _cod_database_code 2000648