# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_14 #============================================================================== _audit_creation_date 09-08-24 _audit_creation_method CRYSTALS_ver_12.86 _oxford_structure_analysis_title CYPRO _chemical_name_systematic . _chemical_melting_point 'not measured' _refine_special_details ; The structure has a number of stereocentres present. It must be stated at this stage that all materials used were racemic, however, the RELATIVE stereochemistry is correct. There was also a minor component of disorder in the acetal ring system, that was modelled. ; _cell_length_a 6.8219(2) _cell_length_b 9.1724(4) _cell_length_c 9.3248(4) _cell_angle_alpha 88.1107(17) _cell_angle_beta 79.4709(16) _cell_angle_gamma 80.956(2) _cell_volume 566.52(4) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 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' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C13 H18 O3 # Dc = 1.30 Fooo = 240.00 Mu = 0.91 M = 222.28 # Found Formula = C13 H18 O3 # Dc = 1.30 FOOO = 240.00 Mu = 0.91 M = 222.28 _chemical_formula_sum 'C13 H18 O3' _chemical_formula_moiety 'C13 H18 O3' _chemical_compound_source . _chemical_formula_weight 222.28 _cell_measurement_reflns_used 2284 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 240 _exptl_absorpt_coefficient_mu 0.091 # Sheldrick geometric approximatio 0.98 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 0.98 # 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 \w # 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 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 8424 _reflns_number_total 2444 _diffrn_reflns_av_R_equivalents 0.036 # Number of reflections with Friedels Law is 4367 # Number of reflections without Friedels Law is 2444 # Theoretical number of reflections is about 2585 _diffrn_reflns_theta_min 5.213 _diffrn_reflns_theta_max 27.433 _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 25.238 _diffrn_measured_fraction_theta_full 0.970 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min -11 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 11 _oxford_diffrn_Wilson_B_factor 2.86 _oxford_diffrn_Wilson_scale 0.42 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.32 _refine_diff_density_max 0.32 # 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>-3.0\s(I) _refine_ls_number_reflns 2444 _refine_ls_number_restraints 90 _refine_ls_number_parameters 173 _oxford_refine_ls_R_factor_ref 0.0750 _refine_ls_wR_factor_ref 0.1182 _refine_ls_goodness_of_fit_ref 1.0019 _refine_ls_shift/su_max 0.001697 # The values computed from all data _oxford_reflns_number_all 2444 _refine_ls_R_factor_all 0.0750 _refine_ls_wR_factor_all 0.1182 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1880 _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_gt 0.1057 # 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, 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: 18.1 23.3 6.85 ; # 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 O1 O 1.5986(2) 0.8267(2) -0.09216(19) 0.0389 1.0000 Uani . . . . . . . C2 C 1.4213(3) 0.8131(2) -0.0699(2) 0.0285 1.0000 Uani . . . . . . . C3 C 1.2749(3) 0.8283(2) 0.0733(2) 0.0252 1.0000 Uani . . . . . . . C4 C 1.1254(3) 0.7216(2) 0.0613(2) 0.0241 1.0000 Uani . . . . . . . C5 C 1.2048(3) 0.5633(2) 0.1038(3) 0.0305 1.0000 Uani . . . . . . . C6 C 1.1089(3) 0.7354(3) -0.1026(2) 0.0286 1.0000 Uani . . . . . . . C7 C 1.2975(3) 0.7915(3) -0.1832(2) 0.0315 1.0000 Uani . . . . . . . C8 C 1.2609(4) 0.6372(3) -0.2085(3) 0.0355 1.0000 Uani . . . . . . . C9 C 0.9277(3) 0.7793(2) 0.1637(2) 0.0266 1.0000 Uani . . . . . . . C10 C 0.9568(3) 0.8070(2) 0.31891(19) 0.0288 1.0000 Uani D . . . . . . O14 O 0.7764(2) 0.89779(15) 0.39242(17) 0.0350 1.0000 Uani D . . . . . . C15 C 1.1354(4) 0.8857(3) 0.3284(3) 0.0347 1.0000 Uani . . . . . . . C16 C 1.3317(3) 0.8279(3) 0.2225(2) 0.0314 1.0000 Uani . . . . . . . O110 O 0.9721(5) 0.6712(3) 0.3987(3) 0.0393 0.781(7) Uani D . P 1 1 . . C120 C 0.8479(5) 0.6966(3) 0.5375(3) 0.0419 0.781(7) Uani D . P 1 1 . . C130 C 0.6767(4) 0.8127(4) 0.5058(4) 0.0360 0.781(7) Uani D . P 1 1 . . O111 O 0.9708(12) 0.671(1) 0.3977(10) 0.0342 0.219(7) Uani D . P 1 2 . . C121 C 0.7757(14) 0.6588(8) 0.4775(11) 0.0391 0.219(7) Uani D . P 1 2 . . C131 C 0.6875(15) 0.8176(9) 0.5170(9) 0.0360 0.219(7) Uani D . P 1 2 . . H31 H 1.1963 0.9294 0.0619 0.0339 1.0000 Uiso R . . . . . . H53 H 1.1204 0.4962 0.0729 0.0507 1.0000 Uiso R . . . . . . H51 H 1.1961 0.5587 0.2107 0.0505 1.0000 Uiso R . . . . . . H52 H 1.3467 0.5360 0.0547 0.0501 1.0000 Uiso R . . . . . . H61 H 0.9743 0.7728 -0.1283 0.0355 1.0000 Uiso R . . . . . . H71 H 1.2909 0.8660 -0.2622 0.0394 1.0000 Uiso R . . . . . . H82 H 1.3515 0.5548 -0.1694 0.0455 1.0000 Uiso R . . . . . . H81 H 1.2255 0.6145 -0.3027 0.0454 1.0000 Uiso R . . . . . . H92 H 0.8708 0.8742 0.1244 0.0343 1.0000 Uiso R . . . . . . H91 H 0.8306 0.7082 0.1693 0.0345 1.0000 Uiso R . . . . . . H151 H 1.1581 0.8755 0.4310 0.0450 1.0000 Uiso R . . . . . . H152 H 1.0952 0.9920 0.3045 0.0446 1.0000 Uiso R . . . . . . H162 H 1.4361 0.8924 0.2229 0.0411 1.0000 Uiso R . . . . . . H161 H 1.3879 0.7263 0.2509 0.0414 1.0000 Uiso R . . . . . . H1202 H 0.9275 0.7358 0.6020 0.0489 0.781(7) Uiso R . P 1 1 . . H1201 H 0.8029 0.6057 0.5796 0.0495 0.781(7) Uiso R . P 1 1 . . H1301 H 0.6191 0.8771 0.5923 0.0457 0.781(7) Uiso R . P 1 1 . . H1302 H 0.5712 0.7651 0.4710 0.0465 0.781(7) Uiso R . P 1 1 . . H1211 H 0.7796 0.5974 0.5643 0.0511 0.219(7) Uiso R . P 1 2 . . H1212 H 0.7060 0.6144 0.4116 0.0510 0.219(7) Uiso R . P 1 2 . . H1311 H 0.7171 0.8506 0.6079 0.0450 0.219(7) Uiso R . P 1 2 . . H1312 H 0.5407 0.8281 0.5227 0.0452 0.219(7) Uiso R . P 1 2 . . 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 O1 0.0236(8) 0.0459(10) 0.0460(10) 0.0038(8) -0.0002(7) -0.0092(7) C2 0.0243(10) 0.0282(11) 0.0309(11) 0.0038(9) 0.0005(9) -0.0049(8) C3 0.0212(9) 0.0266(10) 0.0276(11) 0.0027(8) -0.0028(8) -0.0059(8) C4 0.0215(9) 0.0271(10) 0.0234(10) 0.0019(8) -0.0024(8) -0.0050(8) C5 0.0271(11) 0.0267(11) 0.0362(12) 0.0033(9) -0.0037(9) -0.0025(8) C6 0.0223(10) 0.0372(12) 0.0254(11) 0.0024(9) -0.0042(8) -0.0024(9) C7 0.0257(11) 0.0380(12) 0.0283(11) 0.0053(9) 0.0002(9) -0.0042(9) C8 0.0323(12) 0.0422(13) 0.0309(12) -0.0045(10) -0.0040(10) -0.0033(10) C9 0.0210(10) 0.0283(11) 0.0290(11) 0.0032(8) -0.0025(8) -0.0023(8) C10 0.0284(11) 0.0293(11) 0.0259(10) 0.0041(8) -0.0019(8) 0.0002(8) O14 0.0333(9) 0.0352(9) 0.0289(8) 0.0052(7) 0.0069(7) 0.0022(7) C15 0.0348(12) 0.0394(13) 0.0294(12) -0.0031(10) -0.0041(9) -0.0056(10) C16 0.0268(11) 0.0379(12) 0.0309(12) 0.0004(9) -0.0067(9) -0.0080(9) O110 0.045(2) 0.035(2) 0.031(2) 0.0125(19) 0.002(2) 0.002(2) C120 0.045(2) 0.048(2) 0.0274(16) 0.0107(14) 0.0011(14) -0.0016(15) C130 0.035(2) 0.047(2) 0.0242(19) 0.0074(17) -0.0015(17) -0.0077(19) O111 0.033(7) 0.033(6) 0.032(7) 0.005(6) 0.004(6) -0.004(7) C121 0.038(5) 0.039(5) 0.034(5) 0.006(4) 0.009(4) -0.005(4) C131 0.033(6) 0.040(6) 0.032(6) 0.002(5) 0.004(5) -0.009(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.514(9) 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 O1 . C2 . 1.214(3) yes C2 . C3 . 1.511(3) yes C2 . C7 . 1.503(3) yes C3 . C4 . 1.540(3) yes C3 . C16 . 1.511(3) yes C3 . H31 . 1.008 no C4 . C5 . 1.534(3) yes C4 . C6 . 1.552(3) yes C4 . C9 . 1.532(3) yes C5 . H53 . 0.989 no C5 . H51 . 0.987 no C5 . H52 . 0.989 no C6 . C7 . 1.521(3) yes C6 . C8 . 1.501(3) yes C6 . H61 . 0.997 no C7 . C8 . 1.509(3) yes C7 . H71 . 0.990 no C8 . H82 . 1.002 no C8 . H81 . 0.989 no C9 . C10 . 1.531(3) yes C9 . H92 . 0.983 no C9 . H91 . 0.994 no C10 . O14 . 1.444(2) yes C10 . C15 . 1.527(3) yes C10 . O110 . 1.429(3) yes C10 . O14 . 1.444(2) yes C10 . C15 . 1.527(3) yes C10 . O111 . 1.428(7) yes O14 . C130 . 1.428(3) yes O14 . C131 . 1.444(7) yes C15 . C16 . 1.542(3) yes C15 . H151 . 0.996 no C15 . H152 . 1.000 no C16 . H162 . 0.996 no C16 . H161 . 0.997 no O110 . C120 . 1.416(3) yes C120 . C130 . 1.516(3) yes C120 . H1202 . 0.990 no C120 . H1201 . 0.979 no C130 . H1301 . 0.998 no C130 . H1302 . 1.004 no O111 . C121 . 1.420(6) yes C121 . C131 . 1.516(6) yes C121 . H1211 . 0.972 no C121 . H1212 . 0.976 no C131 . H1311 . 0.974 no C131 . H1312 . 0.982 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 O1 . C2 . C3 . 127.8(2) yes O1 . C2 . C7 . 126.5(2) yes C3 . C2 . C7 . 105.53(17) yes C2 . C3 . C4 . 104.76(17) yes C2 . C3 . C16 . 125.52(18) yes C4 . C3 . C16 . 113.25(17) yes C2 . C3 . H31 . 101.1 no C4 . C3 . H31 . 104.3 no C16 . C3 . H31 . 105.3 no C3 . C4 . C5 . 111.89(17) yes C3 . C4 . C6 . 101.96(16) yes C5 . C4 . C6 . 112.18(18) yes C3 . C4 . C9 . 107.01(17) yes C5 . C4 . C9 . 110.12(17) yes C6 . C4 . C9 . 113.35(17) yes C4 . C5 . H53 . 108.5 no C4 . C5 . H51 . 108.4 no H53 . C5 . H51 . 110.3 no C4 . C5 . H52 . 109.5 no H53 . C5 . H52 . 109.9 no H51 . C5 . H52 . 110.0 no C4 . C6 . C7 . 107.57(17) yes C4 . C6 . C8 . 117.85(19) yes C7 . C6 . C8 . 59.89(15) yes C4 . C6 . H61 . 118.2 no C7 . C6 . H61 . 120.6 no C8 . C6 . H61 . 118.8 no C6 . C7 . C2 . 106.48(18) yes C6 . C7 . C8 . 59.39(15) yes C2 . C7 . C8 . 118.2(2) yes C6 . C7 . H71 . 121.4 no C2 . C7 . H71 . 117.8 no C8 . C7 . H71 . 119.4 no C7 . C8 . C6 . 60.71(15) yes C7 . C8 . H82 . 116.1 no C6 . C8 . H82 . 118.7 no C7 . C8 . H81 . 118.7 no C6 . C8 . H81 . 118.8 no H82 . C8 . H81 . 113.8 no C4 . C9 . C10 . 113.16(17) yes C4 . C9 . H92 . 107.8 no C10 . C9 . H92 . 107.4 no C4 . C9 . H91 . 110.5 no C10 . C9 . H91 . 108.1 no H92 . C9 . H91 . 109.8 no C9 . C10 . O14 . 107.95(17) yes C9 . C10 . C15 . 114.91(15) yes O14 . C10 . C15 . 107.59(17) yes C9 . C10 . O110 . 110.0(2) yes O14 . C10 . O110 . 105.83(8) yes C15 . C10 . O110 . 110.2(3) yes C9 . C10 . O14 . 107.95(17) yes C9 . C10 . C15 . 114.91(15) yes O14 . C10 . C15 . 107.59(17) yes C9 . C10 . O111 . 109.4(6) yes O14 . C10 . O111 . 105.82(9) yes C15 . C10 . O111 . 110.7(5) yes C10 . O14 . C130 . 108.74(8) yes C10 . O14 . C131 . 108.79(10) yes C10 . C15 . C16 . 114.83(18) yes C10 . C15 . H151 . 106.9 no C16 . C15 . H151 . 110.1 no C10 . C15 . H152 . 107.1 no C16 . C15 . H152 . 107.7 no H151 . C15 . H152 . 110.1 no C15 . C16 . C3 . 105.92(18) yes C15 . C16 . H162 . 111.2 no C3 . C16 . H162 . 110.3 no C15 . C16 . H161 . 110.6 no C3 . C16 . H161 . 110.9 no H162 . C16 . H161 . 108.0 no C10 . O110 . C120 . 107.72(9) yes O110 . C120 . C130 . 103.00(9) yes O110 . C120 . H1202 . 107.8 no C130 . C120 . H1202 . 111.3 no O110 . C120 . H1201 . 111.5 no C130 . C120 . H1201 . 113.4 no H1202 . C120 . H1201 . 109.6 no C120 . C130 . O14 . 102.34(9) yes C120 . C130 . H1301 . 111.2 no O14 . C130 . H1301 . 109.2 no C120 . C130 . H1302 . 110.5 no O14 . C130 . H1302 . 111.1 no H1301 . C130 . H1302 . 112.2 no C10 . O111 . C121 . 107.72(10) yes O111 . C121 . C131 . 103.01(10) yes O111 . C121 . H1211 . 112.8 no C131 . C121 . H1211 . 111.2 no O111 . C121 . H1212 . 106.3 no C131 . C121 . H1212 . 114.0 no H1211 . C121 . H1212 . 109.3 no C121 . C131 . O14 . 102.39(10) yes C121 . C131 . H1311 . 114.5 no O14 . C131 . H1311 . 112.0 no C121 . C131 . H1312 . 107.8 no O14 . C131 . H1312 . 110.2 no H1311 . C131 . H1312 . 109.7 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C5 . H51 . O110 . 133 0.99 2.26 3.025(5) yes C5 . H51 . O111 . 133 0.99 2.26 3.019(5) yes C6 . H61 . O1 1_455 157 1.00 2.50 3.435(5) yes C7 . H71 . O14 2_775 162 0.99 2.47 3.424(5) yes _database_code_depnum_ccdc_archive 'CCDC 953764' ####################################################################### # # 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_15 #============================================================================== _audit_creation_date 09-08-24 _audit_creation_method CRYSTALS_ver_12.86 _oxford_structure_analysis_title EPIMER _chemical_name_systematic . _chemical_melting_point 'not measured' _refine_special_details ; The structure has a number of stereocentres present. It must be stated at this stage that all materials used were racemic, however, the RELATIVE stereochemistry is correct. ; _cell_length_a 11.5140(2) _cell_length_b 7.34560(10) _cell_length_c 14.5121(3) _cell_angle_alpha 90 _cell_angle_beta 113.2854(8) _cell_angle_gamma 90 _cell_volume 1127.42(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc ' 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' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C13 H18 O3 # Dc = 1.31 Fooo = 480.00 Mu = 0.92 M = 222.28 # Found Formula = C13 H18 O3 # Dc = 1.31 FOOO = 480.00 Mu = 0.92 M = 222.28 _chemical_formula_sum 'C13 H18 O3' _chemical_formula_moiety 'C13 H18 O3' _chemical_compound_source . _chemical_formula_weight 222.28 _cell_measurement_reflns_used 2691 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.50 _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.092 # Sheldrick geometric approximatio 0.98 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.68 _exptl_absorpt_correction_T_max 0.98 # 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 \w # 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 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 16706 _reflns_number_total 2561 _diffrn_reflns_av_R_equivalents 0.016 # Number of reflections with Friedels Law is 5031 # Number of reflections without Friedels Law is 2561 # Theoretical number of reflections is about 2585 _diffrn_reflns_theta_min 5.363 _diffrn_reflns_theta_max 27.479 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.654 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -14 _reflns_limit_h_max 13 _reflns_limit_k_min 0 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _oxford_diffrn_Wilson_B_factor 2.24 _oxford_diffrn_Wilson_scale 0.80 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.19 _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>3.0\s(I) _refine_ls_number_reflns 1963 _refine_ls_number_restraints 0 _refine_ls_number_parameters 145 _oxford_refine_ls_R_factor_ref 0.0358 _refine_ls_wR_factor_ref 0.0872 _refine_ls_goodness_of_fit_ref 0.9880 _refine_ls_shift/su_max 0.000226 # The values computed from all data _oxford_reflns_number_all 2561 _refine_ls_R_factor_all 0.0479 _refine_ls_wR_factor_all 0.0924 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2085 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_gt 0.0892 # 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^) + ( 0.04P)^2^ + 0.52P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # 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 0.80158(11) 0.36271(17) 0.32650(9) 0.0205 1.0000 Uani . . . . . . . C2 C 0.93852(12) 0.34363(18) 0.33566(10) 0.0240 1.0000 Uani . . . . . . . C3 C 0.97750(13) 0.14445(19) 0.35625(10) 0.0282 1.0000 Uani . . . . . . . C4 C 0.96326(13) 0.23796(19) 0.25816(11) 0.0292 1.0000 Uani . . . . . . . C5 C 0.86394(13) 0.04620(18) 0.35327(10) 0.0266 1.0000 Uani . . . . . . . C6 C 0.74853(12) 0.16723(18) 0.30148(9) 0.0226 1.0000 Uani . . . . . . . C7 C 0.63478(13) 0.12443(19) 0.32706(10) 0.0274 1.0000 Uani . . . . . . . C8 C 0.65685(13) 0.17713(19) 0.43442(10) 0.0278 1.0000 Uani . . . . . . . C9 C 0.69221(12) 0.37606(18) 0.45238(9) 0.0231 1.0000 Uani . . . . . . . C10 C 0.80945(11) 0.41804(18) 0.43141(9) 0.0222 1.0000 Uani . . . . . . . O11 O 0.58594(8) 0.48359(13) 0.39353(7) 0.0280 1.0000 Uani . . . . . . . C12 C 0.60208(15) 0.6548(2) 0.44400(11) 0.0350 1.0000 Uani . . . . . . . C13 C 0.67790(14) 0.6088(2) 0.55429(11) 0.0322 1.0000 Uani . . . . . . . O14 O 0.71433(9) 0.42245(14) 0.55377(7) 0.0311 1.0000 Uani . . . . . . . O15 O 0.86261(10) -0.10276(14) 0.38942(8) 0.0381 1.0000 Uani . . . . . . . C16 C 0.72670(13) 0.49937(19) 0.24556(10) 0.0276 1.0000 Uani . . . . . . . H21 H 0.9987 0.4397 0.3720 0.0295 1.0000 Uiso R . . . . . . H31 H 1.0640 0.1092 0.4056 0.0349 1.0000 Uiso R . . . . . . H41 H 1.0409 0.2646 0.2473 0.0361 1.0000 Uiso R . . . . . . H42 H 0.8936 0.2027 0.1956 0.0364 1.0000 Uiso R . . . . . . H61 H 0.7225 0.1475 0.2279 0.0253 1.0000 Uiso R . . . . . . H71 H 0.6193 -0.0070 0.3181 0.0327 1.0000 Uiso R . . . . . . H72 H 0.5618 0.1937 0.2807 0.0324 1.0000 Uiso R . . . . . . H81 H 0.7297 0.1049 0.4819 0.0360 1.0000 Uiso R . . . . . . H82 H 0.5796 0.1553 0.4476 0.0361 1.0000 Uiso R . . . . . . H101 H 0.8788 0.3476 0.4814 0.0250 1.0000 Uiso R . . . . . . H102 H 0.8260 0.5478 0.4401 0.0254 1.0000 Uiso R . . . . . . H121 H 0.6505 0.7420 0.4178 0.0429 1.0000 Uiso R . . . . . . H122 H 0.5164 0.7047 0.4344 0.0433 1.0000 Uiso R . . . . . . H131 H 0.7572 0.6854 0.5844 0.0397 1.0000 Uiso R . . . . . . H132 H 0.6238 0.6183 0.5946 0.0393 1.0000 Uiso R . . . . . . H161 H 0.6384 0.5000 0.2369 0.0397 1.0000 Uiso R . . . . . . H162 H 0.7585 0.6228 0.2654 0.0400 1.0000 Uiso R . . . . . . H163 H 0.7307 0.4676 0.1819 0.0396 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 0.0213(6) 0.0213(6) 0.0192(6) -0.0003(5) 0.0083(5) -0.0025(5) C2 0.0223(6) 0.0243(6) 0.0253(6) -0.0014(5) 0.0093(5) -0.0039(5) C3 0.0255(7) 0.0286(7) 0.0303(7) 0.0006(6) 0.0107(6) 0.0027(6) C4 0.0288(7) 0.0321(8) 0.0311(7) -0.0013(6) 0.0166(6) -0.0016(6) C5 0.0343(7) 0.0226(7) 0.0249(7) -0.0041(5) 0.0138(6) -0.0018(6) C6 0.0251(6) 0.0237(6) 0.0188(6) -0.0032(5) 0.0084(5) -0.0055(5) C7 0.0283(7) 0.0262(7) 0.0290(7) -0.0039(6) 0.0126(6) -0.0082(5) C8 0.0316(7) 0.0284(7) 0.0284(7) 0.0020(6) 0.0172(6) -0.0028(6) C9 0.0262(6) 0.0267(7) 0.0159(6) 0.0014(5) 0.0078(5) 0.0027(5) C10 0.0236(6) 0.0212(6) 0.0198(6) -0.0029(5) 0.0065(5) -0.0017(5) O11 0.0260(5) 0.0317(5) 0.0252(5) 0.0021(4) 0.0088(4) 0.0050(4) C12 0.0414(8) 0.0290(7) 0.0375(8) 0.0025(6) 0.0187(7) 0.0082(6) C13 0.0349(7) 0.0300(7) 0.0337(8) -0.0060(6) 0.0158(6) 0.0001(6) O14 0.0415(6) 0.0336(6) 0.0199(5) 0.0007(4) 0.0140(4) 0.0084(4) O15 0.0505(6) 0.0224(5) 0.0463(6) 0.0038(5) 0.0242(5) 0.0013(5) C16 0.0292(7) 0.0299(7) 0.0243(7) 0.0051(6) 0.0113(6) 0.0011(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.129(5) 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 . 1.5355(17) yes C1 . C6 . 1.5465(17) yes C1 . C10 . 1.5433(17) yes C1 . C16 . 1.5264(18) yes C2 . C3 . 1.5249(19) yes C2 . C4 . 1.4838(19) yes C2 . H21 . 0.984 no C3 . C4 . 1.5298(19) yes C3 . C5 . 1.4790(19) yes C3 . H31 . 1.004 no C4 . H41 . 0.987 no C4 . H42 . 0.979 no C5 . C6 . 1.5270(19) yes C5 . O15 . 1.2161(17) yes C6 . C7 . 1.5286(17) yes C6 . H61 . 0.999 no C7 . C8 . 1.5260(18) yes C7 . H71 . 0.981 no C7 . H72 . 0.985 no C8 . C9 . 1.5116(19) yes C8 . H81 . 1.001 no C8 . H82 . 0.993 no C9 . C10 . 1.5280(17) yes C9 . O11 . 1.4228(15) yes C9 . O14 . 1.4317(15) yes C10 . H101 . 0.987 no C10 . H102 . 0.971 no O11 . C12 . 1.4304(17) yes C12 . C13 . 1.528(2) yes C12 . H121 . 1.017 no C12 . H122 . 1.009 no C13 . O14 . 1.4328(17) yes C13 . H131 . 1.013 no C13 . H132 . 1.011 no C16 . H161 . 0.974 no C16 . H162 . 0.978 no C16 . H163 . 0.972 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 . C6 . 103.43(10) yes C2 . C1 . C10 . 106.31(10) yes C6 . C1 . C10 . 109.87(10) yes C2 . C1 . C16 . 112.02(10) yes C6 . C1 . C16 . 112.30(10) yes C10 . C1 . C16 . 112.40(11) yes C1 . C2 . C3 . 108.49(10) yes C1 . C2 . C4 . 118.72(11) yes C3 . C2 . C4 . 61.11(9) yes C1 . C2 . H21 . 117.5 no C3 . C2 . H21 . 119.5 no C4 . C2 . H21 . 118.5 no C2 . C3 . C4 . 58.12(9) yes C2 . C3 . C5 . 105.91(11) yes C4 . C3 . C5 . 115.06(11) yes C2 . C3 . H31 . 121.3 no C4 . C3 . H31 . 119.4 no C5 . C3 . H31 . 120.7 no C3 . C4 . C2 . 60.77(9) yes C3 . C4 . H41 . 117.9 no C2 . C4 . H41 . 118.4 no C3 . C4 . H42 . 119.4 no C2 . C4 . H42 . 120.6 no H41 . C4 . H42 . 111.5 no C3 . C5 . C6 . 108.51(11) yes C3 . C5 . O15 . 126.03(13) yes C6 . C5 . O15 . 125.40(13) yes C1 . C6 . C5 . 103.82(10) yes C1 . C6 . C7 . 115.51(10) yes C5 . C6 . C7 . 115.04(11) yes C1 . C6 . H61 . 108.0 no C5 . C6 . H61 . 106.0 no C7 . C6 . H61 . 107.8 no C6 . C7 . C8 . 112.52(11) yes C6 . C7 . H71 . 107.3 no C8 . C7 . H71 . 109.5 no C6 . C7 . H72 . 108.0 no C8 . C7 . H72 . 108.6 no H71 . C7 . H72 . 110.9 no C7 . C8 . C9 . 110.25(11) yes C7 . C8 . H81 . 108.9 no C9 . C8 . H81 . 107.3 no C7 . C8 . H82 . 110.8 no C9 . C8 . H82 . 108.9 no H81 . C8 . H82 . 110.7 no C8 . C9 . C10 . 111.08(10) yes C8 . C9 . O11 . 108.91(11) yes C10 . C9 . O11 . 112.72(10) yes C8 . C9 . O14 . 109.49(10) yes C10 . C9 . O14 . 110.15(10) yes O11 . C9 . O14 . 104.25(10) yes C1 . C10 . C9 . 115.55(10) yes C1 . C10 . H101 . 107.6 no C9 . C10 . H101 . 105.6 no C1 . C10 . H102 . 108.5 no C9 . C10 . H102 . 108.5 no H101 . C10 . H102 . 111.1 no C9 . O11 . C12 . 105.90(10) yes O11 . C12 . C13 . 104.28(11) yes O11 . C12 . H121 . 109.9 no C13 . C12 . H121 . 111.1 no O11 . C12 . H122 . 109.1 no C13 . C12 . H122 . 110.3 no H121 . C12 . H122 . 111.8 no C12 . C13 . O14 . 104.66(11) yes C12 . C13 . H131 . 112.0 no O14 . C13 . H131 . 108.5 no C12 . C13 . H132 . 111.3 no O14 . C13 . H132 . 108.5 no H131 . C13 . H132 . 111.6 no C13 . O14 . C9 . 107.42(10) yes C1 . C16 . H161 . 110.2 no C1 . C16 . H162 . 110.6 no H161 . C16 . H162 . 106.5 no C1 . C16 . H163 . 110.5 no H161 . C16 . H163 . 108.5 no H162 . C16 . H163 . 110.5 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C4 . H42 . O14 4_554 172 0.98 2.45 3.418(2) yes C6 . H61 . O14 4_554 166 1.00 2.54 3.520(2) yes C13 . H132 . O11 2_666 145 1.01 2.60 3.476(2) yes _database_code_depnum_ccdc_archive 'CCDC 953765'