# Supplementary Material (ESI) for Chemical Science # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Chemical Science' _journal_coden_Cambridge 1475 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_address G.Bojase ; Research School of Chemistry, The Australian National University, Canberra, ACT 0200, Australia ; T.V.Nguyen ; Research School of Chemistry, The Australian National University, Canberra, ACT 0200, Australia ; A.D.Payne ; Research School of Chemistry, The Australian National University, Canberra, ACT 0200, Australia ; A.C.Willis ; Research School of Chemistry, The Australian National University, Canberra, ACT 0200, Australia ; M.S.Sherburn ; Research School of Chemistry, The Australian National University, Canberra, ACT 0200, Australia ; _publ_contact_author_name 'Sherburn, Michael' _publ_contact_author_email sherburn@rsc.anu.edu.au _publ_section_title ; Synthesis and properties of the ivyanes: the parent 1,1-oligocyclopropanes ; _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ; ? ; _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? #============================================================================= # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _publ_contact_author_address ; Research School of Chemistry, The Australian National University, Canberra, ACT 0200, Australia ; _publ_contact_author_fax ' 61 2 6125 8114 ' _publ_contact_author_phone ' 61 2 6125 4988 ' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_category ' fo ' _publ_requested_coeditor_name ? # Attachment '- MSS_Ivyane_CCDC766962and766963.cif' data_she0827 _database_code_depnum_ccdc_archive 'CCDC 766962' _audit_creation_date 08-09-12 _audit_creation_method CRYSTALS_ver_12.85 _audit_update_record ; 2008-09-12 - Report on C21 H30 by Anthony C. Willis for BJ and Mick Sherburn 2008-09-12 - passes checkcif tests with minor warnings ; _oxford_structure_analysis_title '9101515 she0827' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 9.5922(5) _cell_length_b 7.2501(4) _cell_length_c 24.0793(12) _cell_angle_alpha 90 _cell_angle_beta 95.810(2) _cell_angle_gamma 90 _cell_volume 1665.98(15) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,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 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 = C19 H26 # Dc = 1.01 Fooo = 624.00 Mu = 0.56 M = 254.42 # Found Formula = C21 H30 # Dc = 1.13 FOOO = 624.00 Mu = 0.62 M = 282.47 _chemical_formula_sum 'C21 H30' _chemical_formula_moiety 'C21 H30' _chemical_compound_source local _chemical_formula_weight 282.47 _cell_measurement_reflns_used 109069 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 25 _cell_measurement_temperature 200 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.03 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.53 _exptl_crystal_density_diffrn 1.126 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.062 # Sheldrick geometric approximatio 0.99 1.00 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.449 # 0.99 _exptl_absorpt_correction_T_max 0.998 # 1.00 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method ' \f and \w scans with CCD ' _diffrn_special_details ; CCD data collecting conditions- phi and omega scans of width 0.5 deg at rate 110 sec/frame, crystal-detector distance 35mm, multiple scan sets so over 90 percent of data collected with 4-fold redundancy or more. ; # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _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 ; ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997) ; _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 25035 _reflns_number_total 2968 _diffrn_reflns_av_R_equivalents 0.102 # Number of reflections with Friedels Law is 2968 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2987 _diffrn_reflns_theta_min 2.591 _diffrn_reflns_theta_max 25.159 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.159 _diffrn_measured_fraction_theta_full 0.989 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 28 _oxford_diffrn_Wilson_B_factor 3.14 _oxford_diffrn_Wilson_scale 4.58 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.50 _refine_diff_density_max 0.53 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 2968 _refine_ls_number_restraints 0 _refine_ls_number_parameters 190 _oxford_refine_ls_R_factor_ref 0.1161 _refine_ls_wR_factor_ref 0.1134 _refine_ls_goodness_of_fit_ref 0.9114 _refine_ls_shift/su_max 0.002759 # The values computed from all data _oxford_reflns_number_all 2968 _refine_ls_R_factor_all 0.1161 _refine_ls_wR_factor_all 0.1134 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1649 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_gt 0.0948 # 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 Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.18P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; #============================================================================== # 4. TEXT _publ_section_abstract #Text of the abstract ; The crystal structure of C~19~H~26~ is reported. ; _publ_section_comment #Text of the paper ; The crystallographic asymmetric unit consists of one C~19~H~26~ molecule. ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions #Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; Crystals of this compound were obtained as very thin fragile plates which diffracted only weakly and spots were of poor quality. Even with long exposure times, the number of reflections with intensities above background is limited. The observation:parameter ratio is therefore lower than we would like but the identity of the compound is clearly established, nonetheless. There do not appear to be any significant refinement anomalies. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:2.3) reflect changes in the illuminated volume of the crystal. They were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). Hydrogen atoms were observed in difference electron density maps prior to their inclusion. They were included at calculated positions and ride on the atoms to which they are respectively bonded. Peaks in the final difference electron density map tend to be all of similar magnitudes and are distributed randomly across the structure and appear to have no chemical significance. ; _publ_section_exptl_prep ; The compound was prepared by GB-M and recrystallized from n-pentane. The sample ID is BJ7DP. ; #**************************************************************************** # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.8. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Johnson, C.K. (1976) ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. ; # 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 _oxford_atom_site_special_shape _atom_site_attached_hydrogens C1 C 0.4589(2) 0.9036(3) 0.41327(8) 0.0394 1.0000 Uani . . . . . . . C2 C 0.5752(2) 1.0439(3) 0.41893(10) 0.0546 1.0000 Uani . . . . . . . C3 C 0.6047(2) 0.8483(3) 0.43503(9) 0.0555 1.0000 Uani . . . . . . . C4 C 0.39124(19) 0.8319(3) 0.35834(8) 0.0359 1.0000 Uani . . . . . . . C5 C 0.3229(2) 0.9714(3) 0.31823(8) 0.0480 1.0000 Uani . . . . . . . C6 C 0.4587(2) 0.8862(3) 0.30689(8) 0.0503 1.0000 Uani . . . . . . . C7 C 0.32952(19) 0.6381(3) 0.36138(7) 0.0343 1.0000 Uani . . . . . . . C8 C 0.3068(2) 0.5244(3) 0.30892(8) 0.0441 1.0000 Uani . . . . . . . C9 C 0.4307(2) 0.4860(3) 0.35045(9) 0.0492 1.0000 Uani . . . . . . . C10 C 0.22761(19) 0.6080(3) 0.40514(7) 0.0360 1.0000 Uani . . . . . . . C11 C 0.2257(2) 0.4232(3) 0.43502(8) 0.0501 1.0000 Uani . . . . . . . C12 C 0.2961(2) 0.5843(3) 0.46449(8) 0.0490 1.0000 Uani . . . . . . . C13 C 0.0852(2) 0.7037(3) 0.39484(8) 0.0389 1.0000 Uani . . . . . . . C14 C 0.0149(2) 0.7754(3) 0.44395(9) 0.0605 1.0000 Uani . . . . . . . C15 C 0.0801(2) 0.9067(3) 0.40649(10) 0.0562 1.0000 Uani . . . . . . . C16 C -0.01715(19) 0.6236(3) 0.34745(8) 0.0376 1.0000 Uani . . . . . . . C17 C -0.1369(2) 0.7413(3) 0.32250(9) 0.0511 1.0000 Uani . . . . . . . C18 C -0.0179(2) 0.6967(3) 0.28908(8) 0.0480 1.0000 Uani . . . . . . . C19 C -0.0453(2) 0.4212(3) 0.35303(8) 0.0390 1.0000 Uani . . . . . . . C20 C -0.1506(2) 0.3515(3) 0.39036(8) 0.0459 1.0000 Uani . . . . . . . C21 C -0.1778(2) 0.3277(3) 0.32835(8) 0.0470 1.0000 Uani . . . . . . . H11 H 0.3941 0.9141 0.4427 0.0457 1.0000 Uiso R . . . . . . H21 H 0.6131 1.0920 0.3857 0.0637 1.0000 Uiso R . . . . . . H22 H 0.5720 1.1380 0.4472 0.0637 1.0000 Uiso R . . . . . . H31 H 0.6553 0.7680 0.4111 0.0653 1.0000 Uiso R . . . . . . H32 H 0.6215 0.8159 0.4741 0.0658 1.0000 Uiso R . . . . . . H51 H 0.2371 0.9353 0.2954 0.0546 1.0000 Uiso R . . . . . . H52 H 0.3221 1.1011 0.3287 0.0553 1.0000 Uiso R . . . . . . H61 H 0.4605 0.7965 0.2770 0.0599 1.0000 Uiso R . . . . . . H62 H 0.5425 0.9662 0.3105 0.0602 1.0000 Uiso R . . . . . . H81 H 0.3255 0.5769 0.2728 0.0522 1.0000 Uiso R . . . . . . H82 H 0.2295 0.4358 0.3068 0.0533 1.0000 Uiso R . . . . . . H91 H 0.5229 0.5245 0.3406 0.0576 1.0000 Uiso R . . . . . . H92 H 0.4348 0.3725 0.3722 0.0568 1.0000 Uiso R . . . . . . H111 H 0.2820 0.3212 0.4218 0.0588 1.0000 Uiso R . . . . . . H112 H 0.1371 0.3825 0.4463 0.0580 1.0000 Uiso R . . . . . . H121 H 0.3979 0.5846 0.4683 0.0578 1.0000 Uiso R . . . . . . H122 H 0.2520 0.6417 0.4958 0.0577 1.0000 Uiso R . . . . . . H141 H -0.0875 0.7693 0.4428 0.0732 1.0000 Uiso R . . . . . . H142 H 0.0626 0.7531 0.4825 0.0734 1.0000 Uiso R . . . . . . H151 H 0.0220 0.9884 0.3805 0.0669 1.0000 Uiso R . . . . . . H152 H 0.1689 0.9689 0.4207 0.0670 1.0000 Uiso R . . . . . . H171 H -0.2271 0.6835 0.3120 0.0594 1.0000 Uiso R . . . . . . H172 H -0.1473 0.8700 0.3355 0.0590 1.0000 Uiso R . . . . . . H181 H -0.0318 0.6081 0.2576 0.0566 1.0000 Uiso R . . . . . . H182 H 0.0455 0.7972 0.2825 0.0563 1.0000 Uiso R . . . . . . H191 H 0.0393 0.3407 0.3515 0.0458 1.0000 Uiso R . . . . . . H201 H -0.1313 0.2415 0.4135 0.0547 1.0000 Uiso R . . . . . . H202 H -0.2061 0.4448 0.4084 0.0545 1.0000 Uiso R . . . . . . H211 H -0.1679 0.2018 0.3132 0.0553 1.0000 Uiso R . . . . . . H212 H -0.2534 0.4010 0.3078 0.0552 1.0000 Uiso 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 C1 0.0355(12) 0.0416(12) 0.0394(12) 0.0004(10) -0.0038(9) -0.0038(10) C2 0.0534(14) 0.0526(14) 0.0547(14) 0.0029(12) -0.0098(11) -0.0198(12) C3 0.0433(14) 0.0648(16) 0.0543(14) 0.0035(13) -0.0152(11) 0.0021(13) C4 0.0335(11) 0.0388(12) 0.0343(11) 0.0043(10) -0.0019(9) -0.0019(10) C5 0.0493(14) 0.0422(13) 0.0495(14) 0.0094(11) -0.0102(11) -0.0076(11) C6 0.0476(14) 0.0575(14) 0.0447(13) 0.0055(11) -0.0004(11) -0.0122(12) C7 0.0330(11) 0.0361(11) 0.0319(11) -0.0009(9) -0.0057(9) 0.0009(10) C8 0.0412(12) 0.0471(13) 0.0436(13) -0.0063(10) 0.0017(10) -0.0002(11) C9 0.0398(13) 0.0454(14) 0.0609(15) -0.0001(11) -0.0023(11) 0.0062(11) C10 0.0354(12) 0.0375(12) 0.0330(11) 0.0038(9) -0.0057(9) -0.0036(10) C11 0.0487(13) 0.0518(14) 0.0469(13) 0.0127(11) -0.0092(11) -0.0086(11) C12 0.0461(13) 0.0648(15) 0.0336(12) 0.0079(11) -0.0081(10) -0.0096(12) C13 0.0372(12) 0.0418(12) 0.0376(11) -0.0047(10) 0.0031(9) -0.0029(10) C14 0.0433(13) 0.0874(19) 0.0515(14) -0.0198(14) 0.0087(11) -0.0041(14) C15 0.0428(13) 0.0505(14) 0.0737(17) -0.0163(13) -0.0022(12) 0.0008(12) C16 0.0348(11) 0.0369(11) 0.0400(12) 0.0003(10) -0.0009(9) -0.0006(10) C17 0.0398(13) 0.0463(13) 0.0645(15) 0.0030(11) -0.0083(11) 0.0033(11) C18 0.0486(13) 0.0520(14) 0.0413(13) 0.0097(11) -0.0060(11) -0.0098(11) C19 0.0348(11) 0.0420(12) 0.0385(12) -0.0006(10) -0.0036(9) -0.0046(10) C20 0.0500(14) 0.0482(13) 0.0394(12) 0.0020(11) 0.0038(10) -0.0095(11) C21 0.0455(13) 0.0508(13) 0.0428(13) -0.0008(11) -0.0048(10) -0.0079(11) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.3896(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 C1 . C2 . 1.505(3) yes C1 . C3 . 1.497(3) yes C1 . C4 . 1.506(3) yes C1 . H11 . 0.992 no C2 . C3 . 1.489(3) yes C2 . H21 . 0.976 no C2 . H22 . 0.966 no C3 . H31 . 0.982 no C3 . H32 . 0.968 no C4 . C5 . 1.503(3) yes C4 . C6 . 1.507(3) yes C4 . C7 . 1.529(3) yes C5 . C6 . 1.491(3) yes C5 . H51 . 0.978 no C5 . H52 . 0.974 no C6 . H61 . 0.972 no C6 . H62 . 0.988 no C7 . C8 . 1.506(3) yes C7 . C9 . 1.510(3) yes C7 . C10 . 1.524(3) yes C8 . C9 . 1.500(3) yes C8 . H81 . 0.982 no C8 . H82 . 0.978 no C9 . H91 . 0.979 no C9 . H92 . 0.974 no C10 . C11 . 1.522(3) yes C10 . C12 . 1.521(2) yes C10 . C13 . 1.530(3) yes C11 . C12 . 1.492(3) yes C11 . H111 . 0.987 no C11 . H112 . 0.964 no C12 . H121 . 0.972 no C12 . H122 . 0.992 no C13 . C14 . 1.512(3) yes C13 . C15 . 1.500(3) yes C13 . C16 . 1.541(3) yes C14 . C15 . 1.492(3) yes C14 . H141 . 0.981 no C14 . H142 . 1.006 no C15 . H151 . 0.991 no C15 . H152 . 0.993 no C16 . C17 . 1.507(3) yes C16 . C18 . 1.501(3) yes C16 . C19 . 1.501(3) yes C17 . C18 . 1.497(3) yes C17 . H171 . 0.971 no C17 . H172 . 0.992 no C18 . H181 . 0.992 no C18 . H182 . 0.973 no C19 . C20 . 1.506(3) yes C19 . C21 . 1.508(3) yes C19 . H191 . 1.003 no C20 . C21 . 1.499(3) yes C20 . H201 . 0.981 no C20 . H202 . 0.988 no C21 . H211 . 0.992 no C21 . H212 . 0.989 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 C2 . C1 . C3 . 59.50(14) yes C2 . C1 . C4 . 124.24(17) yes C3 . C1 . C4 . 121.28(18) yes C2 . C1 . H11 . 113.3 no C3 . C1 . H11 . 113.6 no C4 . C1 . H11 . 114.1 no C1 . C2 . C3 . 59.99(13) yes C1 . C2 . H21 . 120.1 no C3 . C2 . H21 . 118.5 no C1 . C2 . H22 . 117.7 no C3 . C2 . H22 . 120.5 no H21 . C2 . H22 . 111.4 no C1 . C3 . C2 . 60.51(13) yes C1 . C3 . H31 . 117.0 no C2 . C3 . H31 . 120.3 no C1 . C3 . H32 . 117.6 no C2 . C3 . H32 . 119.5 no H31 . C3 . H32 . 112.5 no C1 . C4 . C5 . 116.95(17) yes C1 . C4 . C6 . 116.67(16) yes C5 . C4 . C6 . 59.40(13) yes C1 . C4 . C7 . 114.21(15) yes C5 . C4 . C7 . 120.24(16) yes C6 . C4 . C7 . 118.69(17) yes C4 . C5 . C6 . 60.45(13) yes C4 . C5 . H51 . 117.9 no C6 . C5 . H51 . 119.2 no C4 . C5 . H52 . 119.9 no C6 . C5 . H52 . 118.5 no H51 . C5 . H52 . 112.0 no C4 . C6 . C5 . 60.15(13) yes C4 . C6 . H61 . 118.4 no C5 . C6 . H61 . 119.7 no C4 . C6 . H62 . 119.6 no C5 . C6 . H62 . 117.3 no H61 . C6 . H62 . 112.5 no C4 . C7 . C8 . 119.15(16) yes C4 . C7 . C9 . 113.83(15) yes C8 . C7 . C9 . 59.64(13) yes C4 . C7 . C10 . 116.32(16) yes C8 . C7 . C10 . 116.93(16) yes C9 . C7 . C10 . 118.98(16) yes C7 . C8 . C9 . 60.31(12) yes C7 . C8 . H81 . 120.4 no C9 . C8 . H81 . 117.3 no C7 . C8 . H82 . 116.7 no C9 . C8 . H82 . 117.3 no H81 . C8 . H82 . 114.4 no C7 . C9 . C8 . 60.05(12) yes C7 . C9 . H91 . 116.5 no C8 . C9 . H91 . 117.4 no C7 . C9 . H92 . 121.0 no C8 . C9 . H92 . 120.1 no H91 . C9 . H92 . 112.5 no C7 . C10 . C11 . 119.48(17) yes C7 . C10 . C12 . 114.82(16) yes C11 . C10 . C12 . 58.72(12) yes C7 . C10 . C13 . 116.59(15) yes C11 . C10 . C13 . 115.02(16) yes C12 . C10 . C13 . 119.81(17) yes C10 . C11 . C12 . 60.59(13) yes C10 . C11 . H111 . 118.3 no C12 . C11 . H111 . 120.3 no C10 . C11 . H112 . 117.1 no C12 . C11 . H112 . 118.3 no H111 . C11 . H112 . 112.9 no C10 . C12 . C11 . 60.68(12) yes C10 . C12 . H121 . 115.0 no C11 . C12 . H121 . 116.6 no C10 . C12 . H122 . 119.3 no C11 . C12 . H122 . 118.9 no H121 . C12 . H122 . 115.4 no C10 . C13 . C14 . 119.39(17) yes C10 . C13 . C15 . 117.37(17) yes C14 . C13 . C15 . 59.38(14) yes C10 . C13 . C16 . 116.14(16) yes C14 . C13 . C16 . 114.07(17) yes C15 . C13 . C16 . 118.54(18) yes C13 . C14 . C15 . 59.92(14) yes C13 . C14 . H141 . 119.1 no C15 . C14 . H141 . 119.5 no C13 . C14 . H142 . 118.0 no C15 . C14 . H142 . 118.8 no H141 . C14 . H142 . 112.3 no C13 . C15 . C14 . 60.70(14) yes C13 . C15 . H151 . 119.7 no C14 . C15 . H151 . 121.3 no C13 . C15 . H152 . 117.9 no C14 . C15 . H152 . 118.6 no H151 . C15 . H152 . 110.7 no C13 . C16 . C17 . 119.00(17) yes C13 . C16 . C18 . 120.18(16) yes C17 . C16 . C18 . 59.71(13) yes C13 . C16 . C19 . 114.13(16) yes C17 . C16 . C19 . 116.92(17) yes C18 . C16 . C19 . 116.43(17) yes C16 . C17 . C18 . 59.97(13) yes C16 . C17 . H171 . 118.8 no C18 . C17 . H171 . 118.2 no C16 . C17 . H172 . 120.2 no C18 . C17 . H172 . 118.6 no H171 . C17 . H172 . 112.0 no C16 . C18 . C17 . 60.32(13) yes C16 . C18 . H181 . 118.3 no C17 . C18 . H181 . 120.0 no C16 . C18 . H182 . 118.3 no C17 . C18 . H182 . 116.7 no H181 . C18 . H182 . 113.4 no C16 . C19 . C20 . 121.28(18) yes C16 . C19 . C21 . 123.80(18) yes C20 . C19 . C21 . 59.67(12) yes C16 . C19 . H191 . 114.3 no C20 . C19 . H191 . 114.8 no C21 . C19 . H191 . 112.2 no C19 . C20 . C21 . 60.26(12) yes C19 . C20 . H201 . 120.9 no C21 . C20 . H201 . 118.5 no C19 . C20 . H202 . 117.1 no C21 . C20 . H202 . 118.0 no H201 . C20 . H202 . 112.7 no C19 . C21 . C20 . 60.07(12) yes C19 . C21 . H211 . 116.8 no C20 . C21 . H211 . 117.4 no C19 . C21 . H212 . 120.0 no C20 . C21 . H212 . 118.7 no H211 . C21 . H212 . 113.8 no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag C2 C20 3.568(3) . 1_665 no #------------------------------------------------------------------------------ loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C1 C4 C5 C6 . . . . 106.5(2) no C1 C4 C6 C5 . . . . -107.0(2) no C1 C4 C7 C8 . . . . -158.1(2) no C1 C4 C7 C9 . . . . -90.8(2) no C1 C4 C7 C10 . . . . 53.2(2) no C2 C1 C4 C5 . . . . -58.9(3) no C2 C1 C4 C6 . . . . 8.6(3) no C2 C1 C4 C7 . . . . 153.1(2) no C2 C3 C1 C4 . . . . 113.9(2) no C3 C1 C4 C5 . . . . -131.1(2) no C3 C1 C4 C6 . . . . -63.6(3) no C3 C1 C4 C7 . . . . 80.9(2) no C3 C2 C1 C4 . . . . -109.1(2) no C4 C7 C8 C9 . . . . 102.1(2) no C4 C7 C9 C8 . . . . -111.0(2) no C4 C7 C10 C11 . . . . -144.7(2) no C4 C7 C10 C12 . . . . -78.0(2) no C4 C7 C10 C13 . . . . 69.6(2) no C5 C4 C7 C8 . . . . 55.0(3) no C5 C4 C7 C9 . . . . 122.3(2) no C5 C4 C7 C10 . . . . -93.6(2) no C5 C6 C4 C7 . . . . 110.1(2) no C6 C4 C7 C8 . . . . -14.3(2) no C6 C4 C7 C9 . . . . 53.0(2) no C6 C4 C7 C10 . . . . -163.0(2) no C6 C5 C4 C7 . . . . -107.5(2) no C7 C10 C11 C12 . . . . 102.7(2) no C7 C10 C12 C11 . . . . -110.7(2) no C7 C10 C13 C14 . . . . -145.3(2) no C7 C10 C13 C15 . . . . -76.8(2) no C7 C10 C13 C16 . . . . 71.8(2) no C8 C7 C10 C11 . . . . 66.0(2) no C8 C7 C10 C12 . . . . 132.7(2) no C8 C7 C10 C13 . . . . -79.8(2) no C8 C9 C7 C10 . . . . 106.0(2) no C9 C7 C10 C11 . . . . -2.6(2) no C9 C7 C10 C12 . . . . 64.1(2) no C9 C7 C10 C13 . . . . -148.3(2) no C9 C8 C7 C10 . . . . -109.4(2) no C10 C13 C14 C15 . . . . 106.3(2) no C10 C13 C15 C14 . . . . -109.6(2) no C10 C13 C16 C17 . . . . -160.6(2) no C10 C13 C16 C18 . . . . -90.8(2) no C10 C13 C16 C19 . . . . 54.8(2) no C11 C10 C13 C14 . . . . 67.5(2) no C11 C10 C13 C15 . . . . 136.0(2) no C11 C10 C13 C16 . . . . -75.4(2) no C11 C12 C10 C13 . . . . 102.8(2) no C12 C10 C13 C14 . . . . 0.6(3) no C12 C10 C13 C15 . . . . 69.1(3) no C12 C10 C13 C16 . . . . -142.3(2) no C12 C11 C10 C13 . . . . -111.0(2) no C13 C16 C17 C18 . . . . 110.0(2) no C13 C16 C18 C17 . . . . -108.0(2) no C13 C16 C19 C20 . . . . 81.7(2) no C13 C16 C19 C21 . . . . 154.0(2) no C14 C13 C16 C17 . . . . 54.6(3) no C14 C13 C16 C18 . . . . 124.4(2) no C14 C13 C16 C19 . . . . -90.1(2) no C14 C15 C13 C16 . . . . 102.5(2) no C15 C13 C16 C17 . . . . -12.3(3) no C15 C13 C16 C18 . . . . 57.5(3) no C15 C13 C16 C19 . . . . -157.0(2) no C15 C14 C13 C16 . . . . -110.1(2) no C16 C19 C20 C21 . . . . 113.5(2) no C16 C19 C21 C20 . . . . -109.4(2) no C17 C16 C19 C20 . . . . -63.7(2) no C17 C16 C19 C21 . . . . 8.6(3) no C17 C18 C16 C19 . . . . 107.2(2) no C18 C16 C19 C20 . . . . -131.4(2) no C18 C16 C19 C21 . . . . -59.1(3) no C18 C17 C16 C19 . . . . -106.3(2) no #------------------------------------------------------------------------------ # start Validation Reply Form _vrf_ABSTM02_she0827 ; PROBLEM: The ratio of expected to reported Tmax/Tmin(RR') is < 0.50 RESPONSE: ... Crystals of this compound were obtained as very thin fragile plates which diffracted only weakly and spots were of poor quality. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:2.3) reflect changes in the illuminated volume of the crystal. They were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). ; _vrf_PLAT061_she0827 ; PROBLEM: Tmax/Tmin Range Test RR' too Large ............. 0.46 RESPONSE: ... The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:2.3) reflect changes in the illuminated volume of the crystal. They were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). ; # end Validation Reply Form #===END data_she0828 _database_code_depnum_ccdc_archive 'CCDC 766963' _audit_creation_date 08-09-16 _audit_creation_method CRYSTALS_ver_12.85 _audit_update_record ; 2008-09-16 - Report on C21 H30 by Anthony C. Willis for BJ and Mick Sherburn 2008-09-16 - passes checkcif tests with minor warnings ; _oxford_structure_analysis_title '9111708 she0828_60deg_data ' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 10.5317(2) _cell_length_b 13.1456(2) _cell_length_c 13.7434(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1902.71(5) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c n ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,z x+1/2,-y+1/2,-z x,-y,z+1/2 -x,y,-z+1/2 -x+1/2,-y+1/2,z+1/2 x+1/2,y+1/2,-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 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 = C24 H34 # Dc = 1.13 Fooo = 712.00 Mu = 0.62 M = 161.27 # Found Formula = C24 H34 # Dc = 1.13 FOOO = 712.00 Mu = 0.62 M = 161.27 _chemical_formula_sum 'C24 H34' _chemical_formula_moiety 'C24 H34' _chemical_compound_source local _chemical_formula_weight 322.53 _cell_measurement_reflns_used 16396 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 30 _cell_measurement_temperature 200 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.30 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_max 0.36 _exptl_crystal_density_diffrn 1.126 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.062 # Sheldrick geometric approximatio 0.98 0.98 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.130 0 0 -1 0.230 1 1 0 0.170 -1 -1 0 0.120 -1 1 0 0.140 1 -1 0 0.190 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.978 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; #_diffrn_reflns_av_R_equivalents 0.030 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method ' \f and \w scans with CCD ' _diffrn_special_details ; CCD data collecting conditions- phi and omega scans of width 2.0 deg at rate 100 sec/frame, crystal-detector distance 28mm, multiple scan sets so over 90 percent of data collected with 4-fold redundancy or more. ; # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _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 ; ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997) ; _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 26812 _reflns_number_total 2770 _diffrn_reflns_av_R_equivalents 0.032 # Number of reflections with Friedels Law is 2770 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2784 _diffrn_reflns_theta_min 3.099 _diffrn_reflns_theta_max 30.035 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 30.035 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _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 19 _oxford_diffrn_Wilson_B_factor 2.45 _oxford_diffrn_Wilson_scale 0.57 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.18 _refine_diff_density_max 0.27 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 2770 _refine_ls_number_restraints 0 _refine_ls_number_parameters 160 _oxford_refine_ls_R_factor_ref 0.0563 _refine_ls_wR_factor_ref 0.1291 _refine_ls_goodness_of_fit_ref 0.9501 _refine_ls_shift/su_max 0.003113 # The values computed from all data _oxford_reflns_number_all 2770 _refine_ls_R_factor_all 0.0563 _refine_ls_wR_factor_all 0.1291 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2137 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_gt 0.1249 # 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 Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refxyz # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.08P)^2^ + 0.06P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; #============================================================================== # 4. TEXT _publ_section_abstract #Text of the abstract ; The crystal structure of C~19~H~26~ is reported. ; _publ_section_comment #Text of the paper ; The crystallographic asymmetric unit consists of one half of a C~24~H~34~ molecule. The other half of the molecule is generated by a crystallographic two-fold symmetry operation. ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions #Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; All hydrogen atoms were observed in difference electron density maps prior to their inclusion. H atoms were added at calculated positions and then refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom). Subsequently the H atoms were refined positionally without restraints. Peaks in the final difference electron density map tend to be all of similar magnitudes and are distributed randomly across the structure and appear to have no chemical significance. ; _publ_section_exptl_prep ; The compound was prepared by GB-M and recrystallized from n-pentane. The sample ID is BJ8DPF2. ; #**************************************************************************** # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (2000). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Coppens, P. (1970). The Evaluation of Absorption and Extinction in Single-Crystal Structure Analysis. Crystallographic Computing. F. R. Ahmed, S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 255-270. Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.8. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Johnson, C.K. (1976) ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. ; # 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 _oxford_atom_site_special_shape _atom_site_attached_hydrogens C1 C 0.73037(9) 0.44305(8) 0.38487(7) 0.0364 1.0000 Uani . . . . . . . C2 C 0.64636(11) 0.46268(11) 0.47090(9) 0.0493 1.0000 Uani . . . . . . . C3 C 0.59036(11) 0.46171(11) 0.37081(9) 0.0487 1.0000 Uani . . . . . . . C4 C 0.78991(9) 0.34152(7) 0.36326(6) 0.0314 1.0000 Uani . . . . . . . C5 C 0.85489(12) 0.28701(10) 0.44634(8) 0.0459 1.0000 Uani . . . . . . . C6 C 0.72800(12) 0.25026(9) 0.41071(9) 0.0487 1.0000 Uani . . . . . . . C7 C 0.83985(8) 0.33233(6) 0.25948(6) 0.0276 1.0000 Uani . . . . . . . C8 C 0.85036(11) 0.22780(8) 0.21480(9) 0.0400 1.0000 Uani . . . . . . . C9 C 0.73965(11) 0.29477(9) 0.18844(8) 0.0414 1.0000 Uani . . . . . . . C10 C 0.93489(8) 0.41255(6) 0.22550(6) 0.0263 1.0000 Uani . . . . . . . C11 C 0.93304(11) 0.44404(8) 0.11906(7) 0.0390 1.0000 Uani . . . . . . . C12 C 0.87505(11) 0.51245(8) 0.19306(8) 0.0417 1.0000 Uani . . . . . . . H11 H 0.7828(12) 0.4971(11) 0.3686(9) 0.0436 1.0000 Uiso . . . . . . . H21 H 0.6561(13) 0.5312(12) 0.5020(12) 0.0618 1.0000 Uiso . . . . . . . H22 H 0.6281(14) 0.4050(12) 0.5157(12) 0.0610 1.0000 Uiso . . . . . . . H31 H 0.5597(13) 0.5257(11) 0.3417(10) 0.0587 1.0000 Uiso . . . . . . . H32 H 0.5411(14) 0.4045(11) 0.3541(10) 0.0577 1.0000 Uiso . . . . . . . H51 H 0.8555(13) 0.3247(11) 0.5114(12) 0.0561 1.0000 Uiso . . . . . . . H52 H 0.9319(13) 0.2450(11) 0.4294(10) 0.0546 1.0000 Uiso . . . . . . . H61 H 0.6547(14) 0.2619(12) 0.4498(11) 0.0593 1.0000 Uiso . . . . . . . H62 H 0.7265(14) 0.1865(11) 0.3719(11) 0.0588 1.0000 Uiso . . . . . . . H81 H 0.9171(13) 0.2185(10) 0.1651(10) 0.0469 1.0000 Uiso . . . . . . . H82 H 0.8375(12) 0.1685(10) 0.2548(10) 0.0505 1.0000 Uiso . . . . . . . H91 H 0.7368(13) 0.3220(10) 0.1191(10) 0.0512 1.0000 Uiso . . . . . . . H92 H 0.6596(12) 0.2749(10) 0.2185(10) 0.0495 1.0000 Uiso . . . . . . . H111 H 1.0168(13) 0.4697(9) 0.0959(9) 0.0466 1.0000 Uiso . . . . . . . H112 H 0.8753(12) 0.4069(10) 0.0737(10) 0.0488 1.0000 Uiso . . . . . . . H121 H 0.9181(13) 0.5781(10) 0.2064(10) 0.0510 1.0000 Uiso . . . . . . . H122 H 0.7805(13) 0.5128(11) 0.1935(9) 0.0499 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 C1 0.0345(5) 0.0376(5) 0.0371(5) -0.0059(4) 0.0131(4) -0.0049(4) C2 0.0405(6) 0.0658(8) 0.0416(6) -0.0115(5) 0.0148(5) -0.0027(5) C3 0.0405(6) 0.0571(7) 0.0485(6) -0.0054(5) 0.0067(5) 0.0051(5) C4 0.0328(4) 0.0320(4) 0.0294(4) 0.0013(3) 0.0055(3) -0.0077(3) C5 0.0495(6) 0.0549(7) 0.0332(5) 0.0133(5) 0.0042(4) -0.0027(5) C6 0.0517(7) 0.0446(6) 0.0497(6) 0.0110(5) 0.0117(5) -0.0142(5) C7 0.0312(4) 0.0256(4) 0.0260(4) -0.0021(3) -0.0002(3) -0.0008(3) C8 0.0449(6) 0.0298(5) 0.0453(5) -0.0101(4) -0.0010(4) -0.0033(4) C9 0.0394(5) 0.0448(5) 0.0400(5) -0.0080(4) -0.0086(4) -0.0045(4) C10 0.0325(4) 0.0226(3) 0.0239(4) 0.0015(3) 0.0043(3) 0.0033(3) C11 0.0419(5) 0.0466(6) 0.0285(4) 0.0126(4) 0.0038(4) 0.0112(5) C12 0.0442(5) 0.0316(5) 0.0493(6) 0.0112(4) 0.0113(5) 0.0123(4) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.572(14) 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 C1 . C2 . 1.4991(14) yes C1 . C3 . 1.5073(15) yes C1 . C4 . 1.5043(13) yes C1 . H11 . 0.927(14) no C2 . C3 . 1.4967(18) yes C2 . H21 . 1.002(15) no C2 . H22 . 0.995(16) no C3 . H31 . 0.986(15) no C3 . H32 . 0.942(15) no C4 . C5 . 1.5118(14) yes C4 . C6 . 1.5131(13) yes C4 . C7 . 1.5250(12) yes C5 . C6 . 1.5030(17) yes C5 . H51 . 1.022(16) no C5 . H52 . 1.008(14) no C6 . H61 . 0.954(15) no C6 . H62 . 0.993(15) no C7 . C8 . 1.5092(12) yes C7 . C9 . 1.5201(13) yes C7 . C10 . 1.5271(11) yes C8 . C9 . 1.5052(15) yes C8 . H81 . 0.988(14) no C8 . H82 . 0.964(14) no C9 . H91 . 1.018(14) no C9 . H92 . 0.974(13) no C10 . C10 6_755 1.5280(17) yes C10 . C11 . 1.5204(12) yes C10 . C12 . 1.5232(12) yes C11 . C12 . 1.4885(15) yes C11 . H111 . 0.997(13) no C11 . H112 . 0.998(14) no C12 . H121 . 0.992(14) no C12 . H122 . 0.996(13) 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 C2 . C1 . C3 . 59.71(8) yes C2 . C1 . C4 . 123.67(10) yes C3 . C1 . C4 . 121.80(9) yes C2 . C1 . H11 . 114.2(8) no C3 . C1 . H11 . 115.3(8) no C4 . C1 . H11 . 112.6(8) no C1 . C2 . C3 . 60.41(7) yes C1 . C2 . H21 . 115.5(9) no C3 . C2 . H21 . 116.1(9) no C1 . C2 . H22 . 118.1(9) no C3 . C2 . H22 . 119.0(9) no H21 . C2 . H22 . 116.2(12) no C1 . C3 . C2 . 59.87(7) yes C1 . C3 . H31 . 120.8(8) no C2 . C3 . H31 . 119.7(8) no C1 . C3 . H32 . 116.1(9) no C2 . C3 . H32 . 116.6(9) no H31 . C3 . H32 . 113.7(12) no C1 . C4 . C5 . 117.40(9) yes C1 . C4 . C6 . 116.03(9) yes C5 . C4 . C6 . 59.58(7) yes C1 . C4 . C7 . 113.49(7) yes C5 . C4 . C7 . 120.85(8) yes C6 . C4 . C7 . 119.27(8) yes C4 . C5 . C6 . 60.25(7) yes C4 . C5 . H51 . 115.7(8) no C6 . C5 . H51 . 116.5(8) no C4 . C5 . H52 . 116.7(8) no C6 . C5 . H52 . 117.6(8) no H51 . C5 . H52 . 117.6(11) no C4 . C6 . C5 . 60.16(7) yes C4 . C6 . H61 . 117.7(10) no C5 . C6 . H61 . 119.0(9) no C4 . C6 . H62 . 116.4(8) no C5 . C6 . H62 . 117.4(9) no H61 . C6 . H62 . 115.2(13) no C4 . C7 . C8 . 118.55(8) yes C4 . C7 . C9 . 112.77(8) yes C8 . C7 . C9 . 59.59(7) yes C4 . C7 . C10 . 117.22(7) yes C8 . C7 . C10 . 117.14(8) yes C9 . C7 . C10 . 118.87(8) yes C7 . C8 . C9 . 60.56(6) yes C7 . C8 . H81 . 116.5(8) no C9 . C8 . H81 . 117.2(8) no C7 . C8 . H82 . 119.6(8) no C9 . C8 . H82 . 120.1(8) no H81 . C8 . H82 . 113.2(11) no C7 . C9 . C8 . 59.85(6) yes C7 . C9 . H91 . 120.5(7) no C8 . C9 . H91 . 117.0(8) no C7 . C9 . H92 . 114.6(8) no C8 . C9 . H92 . 114.3(8) no H91 . C9 . H92 . 117.7(11) no C10 6_755 C10 . C7 . 116.97(6) yes C10 6_755 C10 . C11 . 115.82(8) yes C7 . C10 . C11 . 118.29(8) yes C10 6_755 C10 . C12 . 120.02(6) yes C7 . C10 . C12 . 114.44(8) yes C11 . C10 . C12 . 58.56(6) yes C10 . C11 . C12 . 60.82(6) yes C10 . C11 . H111 . 112.8(7) no C12 . C11 . H111 . 112.1(7) no C10 . C11 . H112 . 118.4(8) no C12 . C11 . H112 . 118.2(7) no H111 . C11 . H112 . 120.4(10) no C10 . C12 . C11 . 60.63(6) yes C10 . C12 . H121 . 120.5(8) no C11 . C12 . H121 . 117.7(8) no C10 . C12 . H122 . 114.6(8) no C11 . C12 . H122 . 114.7(8) no H121 . C12 . H122 . 116.8(11) no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag C2 C2 3.333(2) . 2_666 no C2 C3 3.455(2) . 2_666 no #------------------------------------------------------------------------------ loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C1 C4 C5 C6 . . . . 105.6(1) no C1 C4 C6 C5 . . . . -107.89(9) no C1 C4 C7 C8 . . . . -154.69(9) no C1 C4 C7 C9 . . . . -88.1(1) no C1 C4 C7 C10 . . . . 55.5(1) no C2 C1 C4 C5 . . . . -47.2(1) no C2 C1 C4 C6 . . . . 20.4(1) no C2 C1 C4 C7 . . . . 164.04(9) no C2 C3 C1 C4 . . . . 113.2(1) no C3 C1 C4 C5 . . . . -119.7(1) no C3 C1 C4 C6 . . . . -52.2(1) no C3 C1 C4 C7 . . . . 91.5(1) no C3 C2 C1 C4 . . . . -110.1(1) no C4 C7 C8 C9 . . . . 101.04(9) no C4 C7 C9 C8 . . . . -110.78(9) no C4 C7 C10 C10 . . . 6_755 67.0(1) no C4 C7 C10 C11 . . . . -147.05(8) no C4 C7 C10 C12 . . . . -81.0(1) no C5 C4 C7 C8 . . . . 57.7(1) no C5 C4 C7 C9 . . . . 124.4(1) no C5 C4 C7 C10 . . . . -92.0(1) no C5 C6 C4 C7 . . . . 110.6(1) no C6 C4 C7 C8 . . . . -12.3(1) no C6 C4 C7 C9 . . . . 54.3(1) no C6 C4 C7 C10 . . . . -162.08(9) no C6 C5 C4 C7 . . . . -108.0(1) no C7 C10 C10 C7 . . 6_755 6_755 78.4(1) no C7 C10 C10 C11 . . 6_755 6_755 -68.40(6) no C7 C10 C10 C12 . . 6_755 6_755 -135.46(6) no C7 C10 C11 C12 . . . . 102.80(9) no C7 C10 C12 C11 . . . . -109.41(9) no C8 C7 C10 C10 . . . 6_755 -83.2(1) no C8 C7 C10 C11 . . . . 62.7(1) no C8 C7 C10 C12 . . . . 128.79(9) no C8 C9 C7 C10 . . . . 106.29(9) no C9 C7 C10 C10 . . . 6_755 -151.71(9) no C9 C7 C10 C11 . . . . -5.7(1) no C9 C7 C10 C12 . . . . 60.3(1) no C9 C8 C7 C10 . . . . -109.17(9) no C10 C10 C11 C12 . 6_755 6_755 6_755 -110.83(7) no C10 C10 C12 C11 . 6_755 6_755 6_755 103.7(1) no C11 C10 C10 C11 . . 6_755 6_755 144.8(1) no C11 C10 C10 C12 . . 6_755 6_755 77.7(1) no C12 C10 C10 C12 . . 6_755 6_755 10.7(2) no #------------------------------------------------------------------------------ #===END