data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Michael Greaney' _publ_contact_author_address ;School of Chemistry, University of Edinburgh, King's Buildings, West Mains Rd Edinburgh EH9 3JJ ; _publ_contact_author_email Michael.Greaney@ed.ac.uk _publ_contact_author_phone '0131 650 4726' _publ_contact_author_fax '0131 650 4743' loop_ _publ_author_name _publ_author_address C.A.MacGowan ;School of Chemistry, University of Edinburgh, King's Buildings, West Mains Rd Edinburgh EH9 3JJ ; A.-K.Schmieder ;School of Chemistry, University of Edinburgh, King's Buildings, West Mains Rd Edinburgh EH9 3JJ ; L.Roberts ;Pfizer Global Research & Development, Sandwich Laboratories, Ramsgate Rd, Sandwich, Kent, CT13 9NJ, UK' ; 'Michael Greaney' ;School of Chemistry, University of Edinburgh, King's Buildings, West Mains Rd Edinburgh EH9 3JJ ; _publ_section_title ; Synthesis of the guanacastepene A-B hydrazulene ring system through photochemical ring transposition ; data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 638397' _audit_creation_date 04-10-11 _audit_creation_method CRYSTALS_ver_12.39 _oxford_structure_analysis_title 'cm137a in P2(1)/c' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.0186(2) _cell_length_b 14.4410(4) _cell_length_c 26.8635(8) _cell_angle_alpha 90 _cell_angle_beta 91.465(2) _cell_angle_gamma 90 _cell_volume 2334.07(12) _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' 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 8 # Given Formula = C13 H18 O3 # Dc = 1.27 Fooo = 960.00 Mu = 0.89 M = 444.57 # Found Formula = C13 H18 O3 # Dc = 1.27 FOOO = 960.00 Mu = 0.89 M = 444.57 _chemical_formula_sum 'C13 H18 O3' _chemical_formula_moiety 'C13 H18 O3' _chemical_compound_source ? _chemical_formula_weight 222.28 _cell_measurement_reflns_used 3167 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.09 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_max 0.53 _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.089 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Bruker SMART' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'SMART (Siemens, 1993)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _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 16695 _reflns_number_total 5050 _diffrn_reflns_av_R_equivalents 0.029 # Number of reflections with Friedels Law is 5050 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5062 _diffrn_reflns_theta_min 1.601 _diffrn_reflns_theta_max 26.935 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.935 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 33 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 34 _oxford_diffrn_Wilson_B_factor 1.84 _oxford_diffrn_Wilson_scale 2.63 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.48 _refine_diff_density_max 0.54 _refine_ls_number_reflns 5050 _refine_ls_number_restraints 0 _refine_ls_number_parameters 289 #_refine_ls_R_factor_ref 0.0928 _refine_ls_wR_factor_ref 0.1060 _refine_ls_goodness_of_fit_ref 0.8325 #_reflns_number_all 5050 _refine_ls_R_factor_all 0.0928 _refine_ls_wR_factor_all 0.1060 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 3264 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_gt 0.0911 _refine_ls_shift/su_max 0.000409 # 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 noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; p=P(6)*max(Fo^2^,0) + (1-P(6))Fc^2^ Method = SHELXL 97 (Sheldrick,1997) W= 1. / '[Sigma^2^(F*)+(P(1)p)^2^+P(2)p+P(4)+P(5)Sin(theta)'] P(i) are: 0.216E-01 0.00 0.00 0.00 0.00 0.333 ; # Check this file using the IUCr facility at: # http://journals.iucr.org/services/cif/checking/checkfull.html # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached 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 _atom_site_attached_hydrogens C11 C 1.3493(4) 0.16717(17) 1.00948(8) 0.0253 1.0000 Uani . . . . . . C12 C 1.2625(4) 0.26197(16) 0.99649(8) 0.0229 1.0000 Uani . . . . . . C13 C 1.0312(4) 0.25963(16) 0.97137(8) 0.0198 1.0000 Uani . . . . . . C14 C 1.0232(3) 0.19454(15) 0.92493(8) 0.0179 1.0000 Uani . . . . . . C15 C 0.7776(4) 0.17465(17) 0.90999(9) 0.0269 1.0000 Uani . . . . . . C16 C 0.7453(4) 0.09779(18) 0.87141(9) 0.0294 1.0000 Uani . . . . . . C17 C 0.8495(4) 0.00860(17) 0.89006(9) 0.0310 1.0000 Uani . . . . . . C18 C 1.0961(4) 0.02342(17) 0.90241(9) 0.0298 1.0000 Uani . . . . . . C110 C 1.2733(4) 0.09145(16) 0.97757(9) 0.0246 1.0000 Uani . . . . . . C111 C 0.9635(4) 0.35776(16) 0.95762(9) 0.0241 1.0000 Uani . . . . . . C112 C 0.6635(4) 0.45857(18) 0.94071(11) 0.0390 1.0000 Uani . . . . . . C113 C 1.1422(4) 0.23914(17) 0.88085(9) 0.0267 1.0000 Uani . . . . . . C19 C 1.1360(4) 0.10302(16) 0.93794(8) 0.0213 1.0000 Uani . . . . . . C21 C 0.4104(4) 0.14857(16) 0.75401(8) 0.0229 1.0000 Uani . . . . . . C22 C 0.5018(4) 0.23793(16) 0.77523(8) 0.0216 1.0000 Uani . . . . . . C23 C 0.7254(4) 0.26416(15) 0.75357(8) 0.0185 1.0000 Uani . . . . . . C24 C 0.7166(4) 0.26805(15) 0.69546(8) 0.0184 1.0000 Uani . . . . . . C25 C 0.9559(4) 0.27121(17) 0.67598(9) 0.0258 1.0000 Uani . . . . . . C26 C 0.9754(4) 0.25386(17) 0.62007(9) 0.0294 1.0000 Uani . . . . . . C27 C 0.8752(5) 0.16007(17) 0.60649(9) 0.0319 1.0000 Uani . . . . . . C28 C 0.6333(4) 0.15763(17) 0.62153(9) 0.0302 1.0000 Uani . . . . . . C29 C 0.6014(4) 0.18057(15) 0.67570(8) 0.0200 1.0000 Uani . . . . . . C210 C 0.4721(4) 0.12647(16) 0.70321(8) 0.0227 1.0000 Uani . . . . . . C211 C 0.8027(4) 0.35414(16) 0.77841(8) 0.0215 1.0000 Uani . . . . . . C212 C 1.1027(4) 0.45755(17) 0.79152(11) 0.0371 1.0000 Uani . . . . . . C213 C 0.5841(4) 0.35365(16) 0.67721(8) 0.0250 1.0000 Uani . . . . . . H110 H 1.3263 0.0274 0.9856 0.0294 1.0000 Uiso . . . . . . H111 H 1.2544 0.2992 1.0278 0.0275 1.0000 Uiso . . . . . . H112 H 1.3678 0.2922 0.9733 0.0275 1.0000 Uiso . . . . . . H113 H 0.4975 0.4599 0.9414 0.0468 1.0000 Uiso . . . . . . H114 H 0.7126 0.4706 0.9060 0.0468 1.0000 Uiso . . . . . . H115 H 0.7258 0.5074 0.9635 0.0468 1.0000 Uiso . . . . . . H116 H 1.0882 0.4558 0.8285 0.0444 1.0000 Uiso . . . . . . H117 H 1.0165 0.5112 0.7776 0.0444 1.0000 Uiso . . . . . . H118 H 1.2629 0.4644 0.7832 0.0444 1.0000 Uiso . . . . . . H119 H 0.6574 0.4112 0.6903 0.0300 1.0000 Uiso . . . . . . H120 H 0.4289 0.3501 0.6895 0.0300 1.0000 Uiso . . . . . . H121 H 0.5801 0.3551 0.6400 0.0300 1.0000 Uiso . . . . . . H122 H 1.1332 0.1966 0.8515 0.0321 1.0000 Uiso . . . . . . H123 H 1.0689 0.2993 0.8721 0.0321 1.0000 Uiso . . . . . . H124 H 1.3016 0.2504 0.8904 0.0321 1.0000 Uiso . . . . . . H131 H 0.9237 0.2355 0.9960 0.0238 1.0000 Uiso . . . . . . H151 H 0.6975 0.1565 0.9406 0.0322 1.0000 Uiso . . . . . . H152 H 0.7111 0.2328 0.8960 0.0322 1.0000 Uiso . . . . . . H161 H 0.5827 0.0877 0.8650 0.0351 1.0000 Uiso . . . . . . H162 H 0.8168 0.1166 0.8398 0.0351 1.0000 Uiso . . . . . . H171 H 0.7726 -0.0121 0.9207 0.0371 1.0000 Uiso . . . . . . H172 H 0.8330 -0.0400 0.8637 0.0371 1.0000 Uiso . . . . . . H181 H 1.1577 -0.0344 0.9179 0.0356 1.0000 Uiso . . . . . . H182 H 1.1748 0.0365 0.8708 0.0356 1.0000 Uiso . . . . . . H210 H 0.4146 0.0676 0.6881 0.0272 1.0000 Uiso . . . . . . H221 H 0.5212 0.2309 0.8121 0.0259 1.0000 Uiso . . . . . . H222 H 0.3930 0.2887 0.7677 0.0259 1.0000 Uiso . . . . . . H231 H 0.8342 0.2148 0.7636 0.0222 1.0000 Uiso . . . . . . H251 H 1.0191 0.3338 0.6836 0.0310 1.0000 Uiso . . . . . . H252 H 1.0455 0.2230 0.6941 0.0310 1.0000 Uiso . . . . . . H261 H 1.1357 0.2547 0.6112 0.0354 1.0000 Uiso . . . . . . H262 H 0.8940 0.3036 0.6012 0.0354 1.0000 Uiso . . . . . . H271 H 0.9597 0.1101 0.6244 0.0385 1.0000 Uiso . . . . . . H272 H 0.8839 0.1501 0.5697 0.0385 1.0000 Uiso . . . . . . H281 H 0.5735 0.0941 0.6150 0.0363 1.0000 Uiso . . . . . . H282 H 0.5480 0.2035 0.6007 0.0363 1.0000 Uiso . . . . . . O11 O 1.4886(3) 0.15549(13) 1.04302(6) 0.0364 1.0000 Uani . . . . . . O12 O 1.0907(3) 0.41920(12) 0.94793(7) 0.0379 1.0000 Uani . . . . . . O13 O 0.7428(3) 0.36852(11) 0.95691(6) 0.0300 1.0000 Uani . . . . . . O21 O 0.2818(3) 0.10058(12) 0.77737(6) 0.0362 1.0000 Uani . . . . . . O22 O 0.6887(3) 0.40186(12) 0.80403(6) 0.0336 1.0000 Uani . . . . . . O23 O 1.0165(3) 0.37218(11) 0.77012(6) 0.0286 1.0000 Uani . . . . . . 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 C11 0.0236(12) 0.0299(14) 0.0225(12) 0.0034(11) 0.0000(10) 0.0005(11) C12 0.0244(12) 0.0230(13) 0.0213(12) -0.0027(10) -0.0003(9) -0.0017(10) C13 0.0196(11) 0.0218(12) 0.0180(11) -0.0013(10) 0.0032(9) 0.0008(10) C14 0.0170(11) 0.0202(12) 0.0164(11) -0.0001(9) 0.0007(9) 0.0025(9) C15 0.0201(12) 0.0289(14) 0.0315(14) -0.0024(11) -0.0030(10) 0.0034(11) C16 0.0239(12) 0.0321(14) 0.0318(14) -0.0031(12) -0.0058(10) -0.0012(11) C17 0.0365(15) 0.0246(14) 0.0316(14) -0.0061(11) -0.0050(11) -0.0026(12) C18 0.0326(14) 0.0237(14) 0.0327(14) -0.0056(11) -0.0051(11) 0.0053(11) C110 0.0245(12) 0.0194(12) 0.0297(13) 0.0043(10) -0.0032(10) 0.0031(10) C111 0.0237(12) 0.0226(13) 0.0260(13) -0.0035(10) 0.0034(10) 0.0003(10) C112 0.0278(14) 0.0236(14) 0.066(2) 0.0050(14) 0.0013(13) 0.0088(12) C113 0.0315(13) 0.0263(13) 0.0225(12) 0.0004(10) 0.0042(10) -0.0022(11) C19 0.0195(11) 0.0215(12) 0.0231(12) 0.0010(10) 0.0031(9) 0.0001(10) C21 0.0190(11) 0.0245(13) 0.0253(12) 0.0043(10) 0.0002(9) -0.0008(10) C22 0.0213(11) 0.0230(13) 0.0205(11) 0.0002(10) 0.0024(9) 0.0001(10) C23 0.0190(11) 0.0175(12) 0.0192(11) 0.0007(9) 0.0001(9) 0.0017(9) C24 0.0189(11) 0.0175(12) 0.0188(11) 0.0020(9) -0.0002(9) -0.0011(9) C25 0.0221(12) 0.0307(14) 0.0247(12) -0.0012(11) 0.0013(10) -0.0014(11) C26 0.0295(13) 0.0335(15) 0.0254(13) -0.0002(11) 0.0067(10) -0.0054(12) C27 0.0451(16) 0.0282(14) 0.0230(13) -0.0019(11) 0.0107(11) 0.0020(13) C28 0.0416(15) 0.0283(14) 0.0207(12) -0.0025(11) -0.0004(11) -0.0075(12) C29 0.0184(11) 0.0202(12) 0.0211(12) 0.0003(10) -0.0033(9) 0.0028(9) C210 0.0223(12) 0.0205(12) 0.0252(12) -0.0008(10) -0.0012(9) -0.0004(10) C211 0.0226(12) 0.0221(12) 0.0196(11) 0.0019(10) -0.0019(9) 0.0002(10) C212 0.0291(14) 0.0230(14) 0.0590(19) -0.0090(13) -0.0034(13) -0.0060(12) C213 0.0282(13) 0.0217(13) 0.0250(12) 0.0047(10) -0.0022(10) 0.0010(11) O11 0.0373(11) 0.0399(11) 0.0312(10) 0.0015(9) -0.0145(8) 0.0031(9) O12 0.0260(10) 0.0247(10) 0.0633(14) 0.0053(9) 0.0039(9) -0.0018(8) O13 0.0240(9) 0.0216(9) 0.0445(11) 0.0043(8) 0.0019(8) 0.0047(8) O21 0.0414(11) 0.0356(11) 0.0321(10) 0.0006(9) 0.0096(8) -0.0163(9) O22 0.0331(10) 0.0288(10) 0.0393(11) -0.0123(8) 0.0079(8) -0.0008(8) O23 0.0200(8) 0.0248(9) 0.0408(10) -0.0097(8) -0.0012(7) -0.0036(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.6548(10) 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 C11 . C12 . 1.503(3) yes C11 . C110 . 1.456(3) yes C11 . O11 . 1.227(3) yes C12 . C13 . 1.531(3) yes C12 . H111 . 1.000 no C12 . H112 . 1.000 no C13 . C14 . 1.562(3) yes C13 . C111 . 1.518(3) yes C13 . H131 . 1.000 no C14 . C15 . 1.549(3) yes C14 . C113 . 1.540(3) yes C14 . C19 . 1.522(3) yes C15 . C16 . 1.528(3) yes C15 . H151 . 1.000 no C15 . H152 . 1.000 no C16 . C17 . 1.512(3) yes C16 . H161 . 1.000 no C16 . H162 . 1.000 no C17 . C18 . 1.528(3) yes C17 . H171 . 1.000 no C17 . H172 . 1.000 no C18 . C19 . 1.509(3) yes C18 . H181 . 1.000 no C18 . H182 . 1.000 no C110 . C19 . 1.341(3) yes C110 . H110 . 1.000 no C111 . O12 . 1.204(3) yes C111 . O13 . 1.337(3) yes C112 . H113 . 1.000 no C112 . H114 . 1.000 no C112 . H115 . 1.000 no C112 . O13 . 1.448(3) yes C113 . H122 . 1.000 no C113 . H123 . 1.000 no C113 . H124 . 1.000 no C21 . C22 . 1.509(3) yes C21 . C210 . 1.459(3) yes C21 . O21 . 1.224(3) yes C22 . C23 . 1.528(3) yes C22 . H221 . 1.000 no C22 . H222 . 1.000 no C23 . C24 . 1.562(3) yes C23 . C211 . 1.528(3) yes C23 . H231 . 1.000 no C24 . C25 . 1.546(3) yes C24 . C29 . 1.530(3) yes C24 . C213 . 1.544(3) yes C25 . C26 . 1.530(3) yes C25 . H251 . 1.000 no C25 . H252 . 1.000 no C26 . C27 . 1.523(3) yes C26 . H261 . 1.000 no C26 . H262 . 1.000 no C27 . C28 . 1.521(3) yes C27 . H271 . 1.000 no C27 . H272 . 1.000 no C28 . C29 . 1.509(3) yes C28 . H281 . 1.000 no C28 . H282 . 1.000 no C29 . C210 . 1.338(3) yes C210 . H210 . 1.000 no C211 . O22 . 1.202(3) yes C211 . O23 . 1.337(3) yes C212 . H116 . 1.000 no C212 . H117 . 1.000 no C212 . H118 . 1.000 no C212 . O23 . 1.451(3) yes C213 . H119 . 1.000 no C213 . H120 . 1.000 no C213 . H121 . 1.000 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 C12 . C11 . C110 . 116.4(2) yes C12 . C11 . O11 . 121.5(2) yes C110 . C11 . O11 . 121.9(2) yes C11 . C12 . C13 . 112.88(19) yes C11 . C12 . H111 . 108.612 no C13 . C12 . H111 . 108.612 no C11 . C12 . H112 . 108.614 no C13 . C12 . H112 . 108.613 no H111 . C12 . H112 . 109.467 no C12 . C13 . C14 . 111.99(17) yes C12 . C13 . C111 . 108.78(19) yes C14 . C13 . C111 . 111.41(18) yes C12 . C13 . H131 . 108.181 no C14 . C13 . H131 . 108.179 no C111 . C13 . H131 . 108.179 no C13 . C14 . C15 . 109.18(17) yes C13 . C14 . C113 . 110.91(18) yes C15 . C14 . C113 . 109.73(18) yes C13 . C14 . C19 . 109.55(18) yes C15 . C14 . C19 . 108.40(19) yes C113 . C14 . C19 . 109.04(17) yes C14 . C15 . C16 . 114.50(19) yes C14 . C15 . H151 . 108.201 no C16 . C15 . H151 . 108.201 no C14 . C15 . H152 . 108.201 no C16 . C15 . H152 . 108.199 no H151 . C15 . H152 . 109.466 no C15 . C16 . C17 . 110.5(2) yes C15 . C16 . H161 . 109.224 no C17 . C16 . H161 . 109.222 no C15 . C16 . H162 . 109.222 no C17 . C16 . H162 . 109.222 no H161 . C16 . H162 . 109.469 no C16 . C17 . C18 . 110.2(2) yes C16 . C17 . H171 . 109.296 no C18 . C17 . H171 . 109.295 no C16 . C17 . H172 . 109.296 no C18 . C17 . H172 . 109.297 no H171 . C17 . H172 . 109.468 no C17 . C18 . C19 . 112.5(2) yes C17 . C18 . H181 . 108.721 no C19 . C18 . H181 . 108.723 no C17 . C18 . H182 . 108.721 no C19 . C18 . H182 . 108.723 no H181 . C18 . H182 . 109.465 no C11 . C110 . C19 . 123.5(2) yes C11 . C110 . H110 . 118.261 no C19 . C110 . H110 . 118.262 no C13 . C111 . O12 . 124.9(2) yes C13 . C111 . O13 . 111.9(2) yes O12 . C111 . O13 . 123.2(2) yes H113 . C112 . H114 . 109.477 no H113 . C112 . H115 . 109.476 no H114 . C112 . H115 . 109.474 no H113 . C112 . O13 . 109.468 no H114 . C112 . O13 . 109.467 no H115 . C112 . O13 . 109.466 no C14 . C113 . H122 . 109.466 no C14 . C113 . H123 . 109.466 no H122 . C113 . H123 . 109.475 no C14 . C113 . H124 . 109.467 no H122 . C113 . H124 . 109.477 no H123 . C113 . H124 . 109.476 no C14 . C19 . C18 . 117.0(2) yes C14 . C19 . C110 . 123.5(2) yes C18 . C19 . C110 . 119.5(2) yes C22 . C21 . C210 . 116.19(19) yes C22 . C21 . O21 . 121.3(2) yes C210 . C21 . O21 . 122.4(2) yes C21 . C22 . C23 . 112.61(18) yes C21 . C22 . H221 . 108.682 no C23 . C22 . H221 . 108.682 no C21 . C22 . H222 . 108.682 no C23 . C22 . H222 . 108.682 no H221 . C22 . H222 . 109.466 no C22 . C23 . C24 . 112.46(18) yes C22 . C23 . C211 . 107.82(18) yes C24 . C23 . C211 . 114.08(18) yes C22 . C23 . H231 . 107.389 no C24 . C23 . H231 . 107.390 no C211 . C23 . H231 . 107.389 no C23 . C24 . C25 . 109.36(18) yes C23 . C24 . C29 . 108.70(17) yes C25 . C24 . C29 . 108.97(18) yes C23 . C24 . C213 . 110.50(18) yes C25 . C24 . C213 . 110.31(18) yes C29 . C24 . C213 . 108.96(18) yes C24 . C25 . C26 . 115.02(19) yes C24 . C25 . H251 . 108.068 no C26 . C25 . H251 . 108.068 no C24 . C25 . H252 . 108.069 no C26 . C25 . H252 . 108.069 no H251 . C25 . H252 . 109.468 no C25 . C26 . C27 . 109.93(19) yes C25 . C26 . H261 . 109.356 no C27 . C26 . H261 . 109.358 no C25 . C26 . H262 . 109.357 no C27 . C26 . H262 . 109.356 no H261 . C26 . H262 . 109.467 no C26 . C27 . C28 . 109.4(2) yes C26 . C27 . H271 . 109.480 no C28 . C27 . H271 . 109.483 no C26 . C27 . H272 . 109.482 no C28 . C27 . H272 . 109.485 no H271 . C27 . H272 . 109.466 no C27 . C28 . C29 . 113.4(2) yes C27 . C28 . H281 . 108.480 no C29 . C28 . H281 . 108.482 no C27 . C28 . H282 . 108.479 no C29 . C28 . H282 . 108.482 no H281 . C28 . H282 . 109.467 no C24 . C29 . C28 . 116.62(19) yes C24 . C29 . C210 . 123.7(2) yes C28 . C29 . C210 . 119.6(2) yes C21 . C210 . C29 . 123.7(2) yes C21 . C210 . H210 . 118.166 no C29 . C210 . H210 . 118.170 no C23 . C211 . O22 . 124.5(2) yes C23 . C211 . O23 . 112.12(19) yes O22 . C211 . O23 . 123.4(2) yes H116 . C212 . H117 . 109.476 no H116 . C212 . H118 . 109.475 no H117 . C212 . H118 . 109.476 no H116 . C212 . O23 . 109.467 no H117 . C212 . O23 . 109.467 no H118 . C212 . O23 . 109.467 no C24 . C213 . H119 . 109.466 no C24 . C213 . H120 . 109.467 no H119 . C213 . H120 . 109.476 no C24 . C213 . H121 . 109.467 no H119 . C213 . H121 . 109.476 no H120 . C213 . H121 . 109.477 no C112 . O13 . C111 . 115.34(19) yes C212 . O23 . C211 . 115.83(19) yes #===END data_cm036p _database_code_depnum_ccdc_archive 'CCDC 638398' _audit_creation_date 04-03-17 _audit_creation_method CRYSTALS_ver_12.20 # cm036p in P2(1)2(1)2(1) _publ_section_exptl_refinement ; H atoms placed geometrically after each cycle ; _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2003) ; _computing_publication_material ; CRYSTALS (Watkin et al 2003) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 7.2231(3) _cell_angle_alpha 90 _cell_length_b 9.3503(4) _cell_angle_beta 90 _cell_length_c 17.2474(6) _cell_angle_gamma 90 _cell_volume 1164.86(8) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration unk 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_IV_Table_2.2B '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_IV_Table_2.2B '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_IV_Table_2.2B _cell_formula_units_Z 4 _chemical_formula_sum ' C13 H18 O4 ' _chemical_formula_moiety ' C13 H18 O4 ' _chemical_compound_source ; ? ; _chemical_formula_weight 238.28 _cell_measurement_reflns_used 2243 _cell_measurement_theta_min 2 _cell_measurement_theta_max 26 _cell_measurement_temperature 150 _exptl_crystal_description ' lath ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.18 _exptl_crystal_size_mid 0.49 _exptl_crystal_size_max 0.57 _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.100 _diffrn_measurement_device_type ; Bruker SMART ; _diffrn_radiation_monochromator graphite _computing_data_collection ; SMART (Siemens, 1993) ; _computing_data_reduction ; SAINT (Siemens ,1995) ; _computing_cell_refinement ; SAINT (Siemens ,1995) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS (Siemens, 1996) ; _exptl_absorpt_correction_T_min 0.725 _exptl_absorpt_correction_T_max 1.000 # Sheldrick geometric definitions 0.95 0.98 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 8602 _reflns_number_total 1693 _diffrn_reflns_av_R_equivalents 0.03 # Number of reflections with Friedels Law is 1693 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1531 _diffrn_reflns_theta_min 2.362 _diffrn_reflns_theta_max 28.881 _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 27.437 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min 0 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _refine_diff_density_min -0.27 _refine_diff_density_max 0.33 _refine_ls_number_reflns 1693 _refine_ls_number_restraints 0 _refine_ls_number_parameters 154 #_refine_ls_R_factor_ref 0.0664 _refine_ls_wR_factor_ref 0.1074 _refine_ls_goodness_of_fit_ref 0.8705 #_reflns_number_all 1693 _refine_ls_R_factor_all 0.0664 _refine_ls_wR_factor_all 0.1074 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 1320 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_gt 0.1000 _refine_ls_shift/su_max 0.000192 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; p=P(6)*max(Fo^2^,0)+ (1-P(6))Fc^2^ Method = SHELXL 97 (Sheldrick, 1997) W =1. /'[Sigma^2^(F*)+(P(1)p)^2^+P(2)p+P(4)+P(5)Sin(theta)'] P(i) are: 0.456E-01 0.00 0.00 0.00 0.00 0.333 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom 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 _atom_site_attached_hydrogens C1 C 0.1496(5) 0.0532(3) 0.66121(17) 0.0270 1.0000 Uani . . . . . . O2 O -0.1802(3) 0.0702(3) 0.65178(12) 0.0366 1.0000 Uani . . . . . . C3 C -0.0437(4) 0.0522(3) 0.69184(16) 0.0235 1.0000 Uani . . . . . . C4 C -0.0682(4) 0.0341(3) 0.77801(17) 0.0205 1.0000 Uani . . . . . . O5 O -0.0231(3) -0.1073(2) 0.80700(11) 0.0235 1.0000 Uani . . . . . . C6 C 0.0900(4) 0.0126(3) 0.82991(15) 0.0163 1.0000 Uani . . . . . . C7 C 0.2865(4) 0.0132(3) 0.79774(16) 0.0189 1.0000 Uani . . . . . . C8 C 0.2857(4) -0.0287(3) 0.71133(17) 0.0230 1.0000 Uani . . . . . . C9 C 0.4079(4) -0.0967(3) 0.84050(18) 0.0267 1.0000 Uani . . . . . . C10 C 0.0646(4) 0.0646(3) 0.91389(16) 0.0209 1.0000 Uani . . . . . . C11 C 0.1503(5) 0.2111(3) 0.92213(17) 0.0293 1.0000 Uani . . . . . . C12 C 0.3488(5) 0.2168(3) 0.89297(18) 0.0300 1.0000 Uani . . . . . . C13 C 0.3620(4) 0.1660(3) 0.80946(17) 0.0246 1.0000 Uani . . . . . . O14 O -0.1263(3) 0.0725(2) 0.93348(11) 0.0274 1.0000 Uani . . . . . . C15 C -0.1755(4) -0.0594(3) 0.96991(17) 0.0302 1.0000 Uani . . . . . . C16 C 0.0056(5) -0.1255(4) 0.9931(2) 0.0406 1.0000 Uani . . . . . . O17 O 0.1438(3) -0.0310(2) 0.96785(12) 0.0309 1.0000 Uani . . . . . . H11 H 0.1920 0.1548 0.6576 0.0325 1.0000 Uiso . . . . . . H12 H 0.1489 0.0095 0.6083 0.0325 1.0000 Uiso . . . . . . H41 H -0.1744 0.1028 0.7793 0.0246 1.0000 Uiso . . . . . . H81 H 0.2548 -0.1327 0.7077 0.0277 1.0000 Uiso . . . . . . H82 H 0.4129 -0.0121 0.6902 0.0277 1.0000 Uiso . . . . . . H91 H 0.5361 -0.0946 0.8186 0.0322 1.0000 Uiso . . . . . . H92 H 0.4125 -0.0723 0.8970 0.0322 1.0000 Uiso . . . . . . H93 H 0.3542 -0.1944 0.8338 0.0322 1.0000 Uiso . . . . . . H111 H 0.1491 0.2383 0.9782 0.0351 1.0000 Uiso . . . . . . H112 H 0.0746 0.2809 0.8918 0.0351 1.0000 Uiso . . . . . . H121 H 0.4277 0.1541 0.9264 0.0359 1.0000 Uiso . . . . . . H122 H 0.3944 0.3176 0.8962 0.0359 1.0000 Uiso . . . . . . H131 H 0.4949 0.1678 0.7934 0.0294 1.0000 Uiso . . . . . . H132 H 0.2892 0.2329 0.7761 0.0294 1.0000 Uiso . . . . . . H151 H -0.2547 -0.0416 1.0165 0.0363 1.0000 Uiso . . . . . . H152 H -0.2432 -0.1228 0.9328 0.0363 1.0000 Uiso . . . . . . H161 H 0.0113 -0.1372 1.0507 0.0488 1.0000 Uiso . . . . . . H162 H 0.0207 -0.2209 0.9677 0.0488 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 0.0355(17) 0.0274(16) 0.0182(13) -0.0019(13) 0.0048(13) 0.0010(15) O2 0.0384(13) 0.0418(13) 0.0296(12) -0.0032(11) -0.0167(11) 0.0059(13) C3 0.0335(17) 0.0160(13) 0.0209(13) -0.0033(11) -0.0061(13) 0.0026(13) C4 0.0158(13) 0.0182(13) 0.0275(14) 0.0046(12) -0.0020(12) 0.0011(12) O5 0.0221(10) 0.0210(10) 0.0272(10) 0.0022(9) -0.0032(9) -0.0042(9) C6 0.0173(12) 0.0148(12) 0.0169(12) 0.0015(10) 0.0011(11) 0.0000(11) C7 0.0178(14) 0.0200(14) 0.0190(13) 0.0026(12) 0.0015(11) 0.0014(12) C8 0.0209(14) 0.0216(14) 0.0266(14) -0.0009(13) 0.0076(13) 0.0028(13) C9 0.0170(14) 0.0292(16) 0.0340(16) 0.0033(14) -0.0003(14) 0.0050(13) C10 0.0178(14) 0.0265(14) 0.0183(13) 0.0016(12) 0.0012(11) 0.0011(13) C11 0.0389(19) 0.0274(16) 0.0215(14) -0.0066(12) 0.0063(15) -0.0061(15) C12 0.0330(18) 0.0266(15) 0.0305(16) -0.0037(14) 0.0003(15) -0.0116(15) C13 0.0190(14) 0.0271(14) 0.0276(15) 0.0014(13) 0.0027(14) -0.0028(13) O14 0.0253(11) 0.0308(12) 0.0263(10) 0.0027(9) 0.0082(9) 0.0045(10) C15 0.0286(16) 0.0382(18) 0.0237(14) 0.0047(15) 0.0060(14) -0.0079(16) C16 0.042(2) 0.0374(18) 0.0426(19) 0.0173(16) -0.0104(18) -0.0138(18) O17 0.0242(11) 0.0441(13) 0.0245(10) 0.0128(11) -0.0010(10) -0.0008(11) _refine_ls_extinction_method None 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 . C3 . 1.493(4) yes C1 . C8 . 1.517(4) yes C1 . H11 . 1.000 no C1 . H12 . 1.000 no O2 . C3 . 1.216(3) yes C3 . C4 . 1.506(4) yes C4 . O5 . 1.451(3) yes C4 . C6 . 1.466(4) yes C4 . H41 . 1.000 no O5 . C6 . 1.442(3) yes C6 . C7 . 1.524(4) yes C6 . C10 . 1.539(4) yes C7 . C8 . 1.541(4) yes C7 . C9 . 1.539(4) yes C7 . C13 . 1.542(4) yes C8 . H81 . 1.000 no C8 . H82 . 1.000 no C9 . H91 . 1.000 no C9 . H92 . 1.001 no C9 . H93 . 0.999 no C10 . C11 . 1.509(4) yes C10 . O14 . 1.421(3) yes C10 . O17 . 1.412(3) yes C11 . C12 . 1.520(4) yes C11 . H111 . 1.000 no C11 . H112 . 0.999 no C12 . C13 . 1.520(4) yes C12 . H121 . 1.000 no C12 . H122 . 1.000 no C13 . H131 . 1.000 no C13 . H132 . 1.000 no O14 . C15 . 1.429(4) yes C15 . C16 . 1.501(5) yes C15 . H151 . 1.000 no C15 . H152 . 1.000 no C16 . O17 . 1.402(4) yes C16 . H161 . 1.000 no C16 . H162 . 1.000 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 C3 . C1 . C8 . 113.7(2) yes C3 . C1 . H11 . 108.347 no C8 . C1 . H11 . 108.452 no C3 . C1 . H12 . 108.394 no C8 . C1 . H12 . 108.458 no H11 . C1 . H12 . 109.471 no C1 . C3 . O2 . 123.8(2) yes C1 . C3 . C4 . 117.4(2) yes O2 . C3 . C4 . 118.8(3) yes C3 . C4 . O5 . 114.6(2) yes C3 . C4 . C6 . 121.8(2) yes O5 . C4 . C6 . 59.27(16) yes C3 . C4 . H41 . 92.289 no O5 . C4 . H41 . 138.546 no C6 . C4 . H41 . 132.265 no C4 . O5 . C6 . 60.88(16) yes C4 . C6 . O5 . 59.85(17) yes C4 . C6 . C7 . 120.2(2) yes O5 . C6 . C7 . 115.5(2) yes C4 . C6 . C10 . 116.0(2) yes O5 . C6 . C10 . 115.9(2) yes C7 . C6 . C10 . 116.9(2) yes C6 . C7 . C8 . 110.3(2) yes C6 . C7 . C9 . 110.7(2) yes C8 . C7 . C9 . 107.2(2) yes C6 . C7 . C13 . 106.5(2) yes C8 . C7 . C13 . 111.3(2) yes C9 . C7 . C13 . 110.8(2) yes C7 . C8 . C1 . 115.2(2) yes C7 . C8 . H81 . 107.985 no C1 . C8 . H81 . 108.082 no C7 . C8 . H82 . 107.982 no C1 . C8 . H82 . 108.057 no H81 . C8 . H82 . 109.465 no C7 . C9 . H91 . 109.482 no C7 . C9 . H92 . 109.422 no H91 . C9 . H92 . 109.416 no C7 . C9 . H93 . 109.506 no H91 . C9 . H93 . 109.524 no H92 . C9 . H93 . 109.478 no C6 . C10 . C11 . 109.0(2) yes C6 . C10 . O14 . 110.8(2) yes C11 . C10 . O14 . 109.2(2) yes C6 . C10 . O17 . 111.8(2) yes C11 . C10 . O17 . 110.3(2) yes O14 . C10 . O17 . 105.6(2) yes C10 . C11 . C12 . 112.8(3) yes C10 . C11 . H111 . 108.559 no C12 . C11 . H111 . 108.611 no C10 . C11 . H112 . 108.637 no C12 . C11 . H112 . 108.657 no H111 . C11 . H112 . 109.533 no C11 . C12 . C13 . 111.2(3) yes C11 . C12 . H121 . 109.056 no C13 . C12 . H121 . 109.063 no C11 . C12 . H122 . 109.009 no C13 . C12 . H122 . 109.072 no H121 . C12 . H122 . 109.434 no C7 . C13 . C12 . 113.1(2) yes C7 . C13 . H131 . 108.592 no C12 . C13 . H131 . 108.527 no C7 . C13 . H132 . 108.570 no C12 . C13 . H132 . 108.525 no H131 . C13 . H132 . 109.514 no C10 . O14 . C15 . 107.5(2) yes O14 . C15 . C16 . 104.8(2) yes O14 . C15 . H151 . 110.569 no C16 . C15 . H151 . 110.666 no O14 . C15 . H152 . 110.587 no C16 . C15 . H152 . 110.683 no H151 . C15 . H152 . 109.436 no C15 . C16 . O17 . 106.1(2) yes C15 . C16 . H161 . 110.224 no O17 . C16 . H161 . 110.392 no C15 . C16 . H162 . 110.192 no O17 . C16 . H162 . 110.366 no H161 . C16 . H162 . 109.485 no C10 . O17 . C16 . 108.4(2) yes #===END data_mg6001 _database_code_depnum_ccdc_archive 'CCDC 638399' _chemical_compound_source 'C. McGowan' _exptl_crystal_recrystallization_method ; Recrystallisation by evaporation from diethyl ether solution. ; _audit_creation_date 06-06-19 _audit_creation_method CRYSTALS_ver_12.83 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.8884(2) _cell_length_b 8.7287(3) _cell_length_c 10.4626(3) _cell_angle_alpha 90 _cell_angle_beta 103.724(2) _cell_angle_gamma 90 _cell_volume 611.12(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 c 1 ' _symmetry_space_group_name_Hall 'P -2yc' loop_ _symmetry_equiv_pos_as_xyz x,y,z x,-y,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 2 # Given Formula = C14 H22 O2 # Dc = 1.21 Fooo = 244.00 Mu = 0.78 M = 222.33 # Found Formula = C14 H22 O2 # Dc = 1.21 FOOO = 244.00 Mu = 0.78 M = 222.33 _chemical_formula_sum 'C14 H22 O2' _chemical_formula_moiety 'C14 H22 O2' _chemical_formula_weight 222.33 _cell_measurement_reflns_used 6283 _cell_measurement_theta_min 3 _cell_measurement_theta_max 31 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.25 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_max 0.78 _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.078 # Sheldrick geometric approximatio 0.97 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS version 2006/1' _exptl_absorpt_correction_T_min 0.75 _exptl_absorpt_correction_T_max 0.98 _exptl_special_details ; Used Oxford Cryosystems low temperature device. Data collection strategy optimised with COSMO. ; _diffrn_measurement_device_type 'Bruker SMART Apex CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'SMART (Siemens, 1993)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _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 11221 _reflns_number_total 1885 _diffrn_reflns_av_R_equivalents 0.049 # Number of reflections with Friedels Law is 1885 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1887 _diffrn_reflns_theta_min 2.333 _diffrn_reflns_theta_max 30.638 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.638 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.22 _refine_diff_density_max 0.24 _refine_ls_number_reflns 1885 _refine_ls_number_restraints 3 _refine_ls_number_parameters 149 #_refine_ls_R_factor_ref 0.0348 _refine_ls_wR_factor_ref 0.0801 _refine_ls_goodness_of_fit_ref 0.9682 #_reflns_number_all 1885 _refine_ls_R_factor_all 0.0348 _refine_ls_wR_factor_all 0.0801 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1788 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_gt 0.0795 _refine_ls_shift/su_max 0.000191 # 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 unk _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # 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^ + 0.00P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_special_details ; The hydrogen atoms were placed geometrically, except for H(1) which was found in a fourier difference map. The position of the hydroxy hydrogen (H(1)) was refined subject to an O-H distance restraint of 0.84(5) Angstroms. The remaining hydrogens were refined subject to geometric and X-H distance restraints and then constrained to ride on their host atoms. Checkcif output: 061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............0.80 Sadabs corrects for all systematic errors that lead to disparities in the intensities of equivalent data. It is possible that the larger than expected range of transmission is accounted for by crystal decay or absorption by the mounting fibre. 063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.78mm It has been shown (Gorbitz C. H., Acta Cryst. 1999. B55,1090-1098) that this is not in fact a serious problem.795_ALERT_4_C C-Atom in CIF Coordinate List out of Sequence .. C7 The atom list given is intended to be more chemically significant. #=============================================================================== Resolution & Completeness Statistics (Cumulative) #=============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------- 20.82 0.500 1.000 644 644 0 23.01 0.550 1.000 858 858 0 25.24 0.600 1.000 1113 1113 0 #----------------------------------------------------------- ACTA Min. Res. #--- 27.51 0.650 0.999 1414 1412 2 29.84 0.700 0.996 1766 1759 7 30.64 0.717 0.996 1893 1885 8 ; # End of 'script/refcif.dat' # 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 _atom_site_attached_hydrogens C1 C -0.2737(2) 0.46355(15) 0.04774(15) 0.0223 1.0000 Uani . . . . . . O1 O -0.44550(18) 0.45122(13) -0.04196(14) 0.0293 1.0000 Uani D . . . . . C2 C -0.2620(2) 0.60173(17) 0.13365(17) 0.0283 1.0000 Uani . . . . . . C3 C -0.0731(2) 0.69836(16) 0.14665(16) 0.0273 1.0000 Uani . . . . . . C4 C 0.1196(2) 0.62656(16) 0.22831(16) 0.0263 1.0000 Uani . . . . . . C5 C 0.1976(2) 0.48678(15) 0.16655(15) 0.0220 1.0000 Uani . . . . . . C6 C 0.0725(2) 0.33878(14) 0.15612(14) 0.0182 1.0000 Uani . . . . . . C61 C 0.0393(2) 0.29071(16) 0.29077(15) 0.0233 1.0000 Uani . . . . . . C7 C -0.1284(2) 0.35333(15) 0.05756(14) 0.0192 1.0000 Uani . . . . . . C8 C -0.1693(2) 0.22209(15) -0.02603(15) 0.0222 1.0000 Uani . . . . . . O8 O -0.32724(18) 0.19886(12) -0.11263(13) 0.0296 1.0000 Uani . . . . . . C9 C 0.0034(2) 0.11298(15) 0.00751(16) 0.0268 1.0000 Uani . . . . . . C10 C 0.1758(2) 0.20660(14) 0.09224(15) 0.0203 1.0000 Uani . . . . . . C11 C 0.3288(2) 0.10237(16) 0.18380(15) 0.0236 1.0000 Uani . . . . . . C12 C 0.4028(3) -0.02063(19) 0.10147(18) 0.0336 1.0000 Uani . . . . . . C13 C 0.5098(2) 0.18644(18) 0.26637(17) 0.0303 1.0000 Uani . . . . . . H1 H -0.437(3) 0.363(2) -0.077(2) 0.0431 1.0000 Uiso D . . . . . H21 H -0.3784 0.6616 0.1001 0.0346 1.0000 Uiso R . . . . . H22 H -0.2673 0.5672 0.2209 0.0338 1.0000 Uiso R . . . . . H31 H -0.0942 0.7952 0.1889 0.0339 1.0000 Uiso R . . . . . H32 H -0.0565 0.7190 0.0570 0.0316 1.0000 Uiso R . . . . . H41 H 0.2249 0.7035 0.2404 0.0318 1.0000 Uiso R . . . . . H42 H 0.1000 0.5997 0.3143 0.0298 1.0000 Uiso R . . . . . H51 H 0.3315 0.4636 0.2170 0.0255 1.0000 Uiso R . . . . . H52 H 0.2094 0.5164 0.0798 0.0258 1.0000 Uiso R . . . . . H611 H -0.0217 0.1886 0.2876 0.0353 1.0000 Uiso R . . . . . H612 H -0.0468 0.3583 0.3208 0.0352 1.0000 Uiso R . . . . . H613 H 0.1619 0.2873 0.3558 0.0346 1.0000 Uiso R . . . . . H91 H 0.0367 0.0754 -0.0708 0.0312 1.0000 Uiso R . . . . . H92 H -0.0312 0.0285 0.0591 0.0329 1.0000 Uiso R . . . . . H101 H 0.2429 0.2570 0.0302 0.0248 1.0000 Uiso R . . . . . H111 H 0.2638 0.0500 0.2446 0.0288 1.0000 Uiso R . . . . . H121 H 0.5021 -0.0817 0.1608 0.0508 1.0000 Uiso R . . . . . H122 H 0.4619 0.0260 0.0351 0.0505 1.0000 Uiso R . . . . . H123 H 0.2994 -0.0902 0.0578 0.0498 1.0000 Uiso R . . . . . H131 H 0.6046 0.1154 0.3185 0.0435 1.0000 Uiso R . . . . . H132 H 0.4758 0.2584 0.3249 0.0434 1.0000 Uiso R . . . . . H133 H 0.5757 0.2409 0.2078 0.0443 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 0.0234(6) 0.0241(6) 0.0191(5) 0.0029(5) 0.0048(4) 0.0005(5) O1 0.0228(5) 0.0350(6) 0.0272(5) 0.0028(4) -0.0002(4) 0.0032(4) C2 0.0292(6) 0.0263(6) 0.0303(7) -0.0019(5) 0.0086(5) 0.0065(5) C3 0.0372(7) 0.0185(6) 0.0269(7) -0.0014(5) 0.0090(6) 0.0022(5) C4 0.0322(7) 0.0213(6) 0.0240(6) -0.0046(5) 0.0040(5) -0.0040(5) C5 0.0231(6) 0.0197(5) 0.0225(6) -0.0018(5) 0.0038(4) -0.0036(4) C6 0.0194(5) 0.0182(5) 0.0160(5) 0.0007(4) 0.0026(4) -0.0010(4) C61 0.0254(6) 0.0271(6) 0.0174(5) 0.0033(4) 0.0053(5) 0.0013(5) C7 0.0192(5) 0.0208(5) 0.0169(5) 0.0007(4) 0.0029(4) -0.0020(4) C8 0.0256(6) 0.0204(6) 0.0194(5) 0.0010(5) 0.0028(4) -0.0036(4) O8 0.0308(5) 0.0300(5) 0.0234(5) -0.0015(4) -0.0024(4) -0.0061(4) C9 0.0317(7) 0.0197(6) 0.0257(7) -0.0032(5) 0.0007(5) 0.0002(5) C10 0.0227(5) 0.0184(5) 0.0198(5) 0.0013(4) 0.0047(4) 0.0019(4) C11 0.0246(6) 0.0220(6) 0.0240(6) 0.0043(5) 0.0056(5) 0.0033(5) C12 0.0384(8) 0.0276(7) 0.0352(7) 0.0024(6) 0.0099(7) 0.0119(6) C13 0.0232(6) 0.0309(7) 0.0341(7) 0.0067(6) 0.0015(5) 0.0024(5) _refine_ls_extinction_coef 138(19) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 1.747(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 . O1 . 1.3289(16) yes C1 . C2 . 1.495(2) yes C1 . C7 . 1.3742(18) yes O1 . H1 . 0.86(2) no C2 . C3 . 1.529(2) yes C2 . H21 . 0.952 no C2 . H22 . 0.970 no C3 . C4 . 1.532(2) yes C3 . H31 . 0.981 no C3 . H32 . 0.988 no C4 . C5 . 1.5359(19) yes C4 . H41 . 0.974 no C4 . H42 . 0.970 no C5 . C6 . 1.5423(17) yes C5 . H51 . 0.969 no C5 . H52 . 0.966 no C6 . C61 . 1.5382(17) yes C6 . C7 . 1.5224(16) yes C6 . C10 . 1.5844(17) yes C61 . H611 . 0.982 no C61 . H612 . 0.941 no C61 . H613 . 0.951 no C7 . C8 . 1.4282(18) yes C8 . O8 . 1.2560(16) yes C8 . C9 . 1.499(2) yes C9 . C10 . 1.5376(19) yes C9 . H91 . 0.959 no C9 . H92 . 0.976 no C10 . C11 . 1.5418(18) yes C10 . H101 . 0.984 no C11 . C12 . 1.537(2) yes C11 . C13 . 1.526(2) yes C11 . H111 . 0.975 no C12 . H121 . 0.967 no C12 . H122 . 0.974 no C12 . H123 . 0.965 no C13 . H131 . 0.970 no C13 . H132 . 0.945 no C13 . H133 . 0.970 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 . C1 . C2 . 113.70(12) yes O1 . C1 . C7 . 120.45(12) yes C2 . C1 . C7 . 125.83(12) yes C1 . O1 . H1 . 103.5(16) no C1 . C2 . C3 . 114.96(12) yes C1 . C2 . H21 . 107.5 no C3 . C2 . H21 . 110.8 no C1 . C2 . H22 . 107.8 no C3 . C2 . H22 . 108.0 no H21 . C2 . H22 . 107.5 no C2 . C3 . C4 . 115.49(12) yes C2 . C3 . H31 . 107.5 no C4 . C3 . H31 . 107.6 no C2 . C3 . H32 . 107.7 no C4 . C3 . H32 . 108.9 no H31 . C3 . H32 . 109.5 no C3 . C4 . C5 . 115.69(11) yes C3 . C4 . H41 . 108.1 no C5 . C4 . H41 . 106.2 no C3 . C4 . H42 . 108.9 no C5 . C4 . H42 . 109.7 no H41 . C4 . H42 . 108.0 no C4 . C5 . C6 . 116.74(11) yes C4 . C5 . H51 . 108.6 no C6 . C5 . H51 . 107.9 no C4 . C5 . H52 . 107.4 no C6 . C5 . H52 . 109.2 no H51 . C5 . H52 . 106.6 no C5 . C6 . C61 . 111.44(10) yes C5 . C6 . C7 . 112.39(10) yes C61 . C6 . C7 . 109.54(10) yes C5 . C6 . C10 . 109.91(9) yes C61 . C6 . C10 . 111.52(10) yes C7 . C6 . C10 . 101.67(10) yes C6 . C61 . H611 . 111.8 no C6 . C61 . H612 . 112.1 no H611 . C61 . H612 . 106.3 no C6 . C61 . H613 . 111.3 no H611 . C61 . H613 . 107.3 no H612 . C61 . H613 . 107.7 no C6 . C7 . C1 . 129.63(11) yes C6 . C7 . C8 . 111.31(11) yes C1 . C7 . C8 . 118.78(12) yes C7 . C8 . O8 . 125.63(13) yes C7 . C8 . C9 . 109.62(12) yes O8 . C8 . C9 . 124.73(12) yes C8 . C9 . C10 . 105.00(11) yes C8 . C9 . H91 . 110.8 no C10 . C9 . H91 . 111.5 no C8 . C9 . H92 . 108.9 no C10 . C9 . H92 . 109.8 no H91 . C9 . H92 . 110.7 no C9 . C10 . C6 . 105.51(10) yes C9 . C10 . C11 . 111.42(11) yes C6 . C10 . C11 . 118.48(10) yes C9 . C10 . H101 . 106.0 no C6 . C10 . H101 . 106.3 no C11 . C10 . H101 . 108.3 no C10 . C11 . C12 . 109.43(11) yes C10 . C11 . C13 . 114.47(11) yes C12 . C11 . C13 . 108.57(12) yes C10 . C11 . H111 . 109.3 no C12 . C11 . H111 . 107.7 no C13 . C11 . H111 . 107.2 no C11 . C12 . H121 . 107.7 no C11 . C12 . H122 . 111.0 no H121 . C12 . H122 . 109.7 no C11 . C12 . H123 . 113.6 no H121 . C12 . H123 . 106.7 no H122 . C12 . H123 . 108.2 no C11 . C13 . H131 . 111.2 no C11 . C13 . H132 . 113.1 no H131 . C13 . H132 . 107.3 no C11 . C13 . H133 . 108.7 no H131 . C13 . H133 . 108.4 no H132 . C13 . H133 . 108.0 no