# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012 data_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name R.S.Rathore _publ_contact_author_email 'ravindranath rathore@yahoo.com' loop_ _publ_author_name N.S.Karthikeyan G.Ramachandran K.Sathiyanarayanan R.S.Rathore data_4f _database_code_depnum_ccdc_archive 'CCDC 843588' #TrackingRef '- 4f_deposit msc13_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-[hydroxy(4-methylphenyl)methyl]cyclododecanone ; _chemical_name_common 2-(hydroxy(4-methylphenyl)methyl)cyclododecanone _chemical_melting_point ? _chemical_formula_moiety 'C20 H30 O2' _chemical_formula_sum 'C20 H30 O2' _chemical_formula_weight 302.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.0425(6) _cell_length_b 6.0319(3) _cell_length_c 12.6615(6) _cell_angle_alpha 90.00 _cell_angle_beta 106.214(5) _cell_angle_gamma 90.00 _cell_volume 883.14(7) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 3020 _cell_measurement_theta_min 2.7436 _cell_measurement_theta_max 29.0651 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.137 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.80601 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details '(CrysAlis Pro; Oxford Diffraction, 2010)' _exptl_special_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur Eos Gemini' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 15.9821 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 6355 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0484 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 29.13 _reflns_number_total 3638 _reflns_number_gt 2508 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0473P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(12) _refine_ls_number_reflns 3638 _refine_ls_number_parameters 204 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0706 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.0917 _refine_ls_wR_factor_gt 0.0846 _refine_ls_goodness_of_fit_ref 0.942 _refine_ls_restrained_S_all 0.942 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.63234(15) 0.2219(3) 0.67889(13) 0.0375(4) Uani 1 1 d . . . C2 C 0.51763(15) 0.2968(3) 0.69469(13) 0.0330(4) Uani 1 1 d . . . H2 H 0.5049 0.4506 0.6693 0.040 Uiso 1 1 calc R . . C3 C 0.51969(16) 0.2927(3) 0.81681(14) 0.0404(5) Uani 1 1 d . . . H3A H 0.4426 0.3247 0.8223 0.049 Uiso 1 1 calc R . . H3B H 0.5401 0.1445 0.8455 0.049 Uiso 1 1 calc R . . C4 C 0.60401(17) 0.4571(3) 0.88794(14) 0.0488(5) Uani 1 1 d . . . H4A H 0.5757 0.6062 0.8680 0.059 Uiso 1 1 calc R . . H4B H 0.6781 0.4432 0.8723 0.059 Uiso 1 1 calc R . . C5 C 0.62188(19) 0.4252(4) 1.01112(15) 0.0590(6) Uani 1 1 d . . . H5A H 0.6599 0.5558 1.0494 0.071 Uiso 1 1 calc R . . H5B H 0.5468 0.4136 1.0249 0.071 Uiso 1 1 calc R . . C6 C 0.69289(18) 0.2226(4) 1.05868(16) 0.0603(6) Uani 1 1 d . . . H6A H 0.6614 0.0954 1.0133 0.072 Uiso 1 1 calc R . . H6B H 0.6846 0.1953 1.1316 0.072 Uiso 1 1 calc R . . C7 C 0.82129(18) 0.2403(4) 1.06697(18) 0.0623(6) Uani 1 1 d . . . H7A H 0.8305 0.3400 1.0099 0.075 Uiso 1 1 calc R . . H7B H 0.8606 0.3065 1.1373 0.075 Uiso 1 1 calc R . . C8 C 0.88008(19) 0.0225(4) 1.05638(17) 0.0658(7) Uani 1 1 d . . . H8A H 0.9625 0.0484 1.0715 0.079 Uiso 1 1 calc R . . H8B H 0.8687 -0.0792 1.1118 0.079 Uiso 1 1 calc R . . C9 C 0.83696(19) -0.0867(4) 0.94466(16) 0.0595(6) Uani 1 1 d . . . H9A H 0.7540 -0.1064 0.9285 0.071 Uiso 1 1 calc R . . H9B H 0.8713 -0.2330 0.9489 0.071 Uiso 1 1 calc R . . C10 C 0.86195(17) 0.0367(4) 0.84935(15) 0.0546(5) Uani 1 1 d . . . H10A H 0.9445 0.0315 0.8577 0.065 Uiso 1 1 calc R . . H10B H 0.8405 0.1910 0.8526 0.065 Uiso 1 1 calc R . . C11 C 0.79848(18) -0.0558(4) 0.73694(16) 0.0576(6) Uani 1 1 d . . . H11A H 0.8124 -0.2142 0.7366 0.069 Uiso 1 1 calc R . . H11B H 0.8301 0.0111 0.6820 0.069 Uiso 1 1 calc R . . C12 C 0.66863(16) -0.0151(3) 0.70511(15) 0.0453(5) Uani 1 1 d . . . H12A H 0.6326 -0.1057 0.6414 0.054 Uiso 1 1 calc R . . H12B H 0.6391 -0.0645 0.7650 0.054 Uiso 1 1 calc R . . C13 C 0.41842(15) 0.1565(3) 0.62286(12) 0.0359(4) Uani 1 1 d . . . H13 H 0.4256 0.0041 0.6507 0.043 Uiso 1 1 calc R . . C14 C 0.30127(14) 0.2475(3) 0.62315(12) 0.0339(4) Uani 1 1 d . . . C15 C 0.22864(16) 0.1312(3) 0.67035(13) 0.0408(4) Uani 1 1 d . . . H15 H 0.2512 -0.0074 0.7011 0.049 Uiso 1 1 calc R . . C16 C 0.12303(17) 0.2174(4) 0.67268(15) 0.0475(5) Uani 1 1 d . . . H16 H 0.0756 0.1348 0.7045 0.057 Uiso 1 1 calc R . . C17 C 0.08619(15) 0.4226(3) 0.62902(13) 0.0433(5) Uani 1 1 d . . . C18 C 0.15838(17) 0.5373(3) 0.58041(14) 0.0480(5) Uani 1 1 d . . . H18 H 0.1352 0.6751 0.5490 0.058 Uiso 1 1 calc R . . C19 C 0.26438(16) 0.4525(3) 0.57711(14) 0.0437(5) Uani 1 1 d . . . H19 H 0.3110 0.5337 0.5438 0.052 Uiso 1 1 calc R . . C20 C -0.02685(17) 0.5214(4) 0.63479(17) 0.0661(7) Uani 1 1 d . . . H20A H -0.0625 0.5980 0.5674 0.099 Uiso 1 1 calc R . . H20B H -0.0129 0.6237 0.6951 0.099 Uiso 1 1 calc R . . H20C H -0.0772 0.4053 0.6455 0.099 Uiso 1 1 calc R . . O1 O 0.69149(12) 0.3476(2) 0.64332(12) 0.0575(4) Uani 1 1 d . . . O2 O 0.43574(12) 0.1585(2) 0.51615(10) 0.0471(4) Uani 1 1 d . . . H2O H 0.392(2) 0.053(5) 0.482(2) 0.093(9) Uiso 1 1 d . . . 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 0.0346(9) 0.0452(12) 0.0317(8) -0.0012(8) 0.0078(8) -0.0032(9) C2 0.0318(10) 0.0338(10) 0.0351(9) 0.0006(7) 0.0119(8) -0.0006(7) C3 0.0355(10) 0.0521(12) 0.0367(10) -0.0060(8) 0.0150(8) -0.0052(8) C4 0.0496(12) 0.0487(12) 0.0476(10) -0.0104(9) 0.0130(9) -0.0045(10) C5 0.0567(14) 0.0751(16) 0.0463(11) -0.0212(11) 0.0162(10) -0.0058(12) C6 0.0563(13) 0.0825(18) 0.0405(10) -0.0023(10) 0.0109(9) -0.0110(13) C7 0.0476(13) 0.0783(17) 0.0537(12) -0.0089(11) 0.0018(10) -0.0144(12) C8 0.0518(13) 0.0785(17) 0.0596(13) 0.0145(12) 0.0030(11) -0.0010(12) C9 0.0586(13) 0.0550(14) 0.0612(13) 0.0101(11) 0.0109(10) 0.0060(12) C10 0.0369(11) 0.0655(13) 0.0623(12) 0.0111(11) 0.0155(10) 0.0079(10) C11 0.0551(13) 0.0627(15) 0.0590(12) 0.0012(11) 0.0227(10) 0.0186(11) C12 0.0470(12) 0.0452(13) 0.0428(10) -0.0028(8) 0.0110(9) 0.0065(9) C13 0.0386(10) 0.0369(10) 0.0331(8) 0.0020(8) 0.0113(8) -0.0017(8) C14 0.0326(9) 0.0389(11) 0.0279(8) -0.0028(7) 0.0051(7) -0.0015(8) C15 0.0399(11) 0.0407(11) 0.0409(9) 0.0040(9) 0.0099(8) -0.0022(9) C16 0.0374(11) 0.0630(14) 0.0451(10) 0.0033(9) 0.0163(8) -0.0076(10) C17 0.0356(10) 0.0573(13) 0.0336(9) -0.0066(10) 0.0039(8) 0.0041(10) C18 0.0507(13) 0.0412(11) 0.0479(11) 0.0048(9) 0.0069(10) 0.0121(10) C19 0.0429(11) 0.0457(12) 0.0443(10) 0.0068(9) 0.0150(8) 0.0013(9) C20 0.0479(13) 0.0859(18) 0.0620(13) -0.0097(12) 0.0111(11) 0.0172(12) O1 0.0430(8) 0.0659(9) 0.0701(10) 0.0211(7) 0.0266(7) 0.0021(7) O2 0.0506(8) 0.0567(9) 0.0365(7) -0.0075(6) 0.0163(6) -0.0024(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.210(2) . ? C1 C12 1.505(3) . ? C1 C2 1.519(3) . ? C2 C13 1.537(2) . ? C2 C3 1.540(2) . ? C2 H2 0.9800 . ? C3 C4 1.522(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.526(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.517(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.524(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.516(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.515(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.518(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.521(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.522(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 O2 1.4235(19) . ? C13 C14 1.515(2) . ? C13 H13 0.9800 . ? C14 C15 1.381(2) . ? C14 C19 1.386(2) . ? C15 C16 1.382(3) . ? C15 H15 0.9300 . ? C16 C17 1.378(3) . ? C16 H16 0.9300 . ? C17 C18 1.383(3) . ? C17 C20 1.506(3) . ? C18 C19 1.387(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? O2 H2O 0.86(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C12 120.83(17) . . ? O1 C1 C2 120.95(17) . . ? C12 C1 C2 118.19(16) . . ? C1 C2 C13 110.10(14) . . ? C1 C2 C3 111.54(14) . . ? C13 C2 C3 112.16(13) . . ? C1 C2 H2 107.6 . . ? C13 C2 H2 107.6 . . ? C3 C2 H2 107.6 . . ? C4 C3 C2 113.89(15) . . ? C4 C3 H3A 108.8 . . ? C2 C3 H3A 108.8 . . ? C4 C3 H3B 108.8 . . ? C2 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C3 C4 C5 113.78(17) . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4B 108.8 . . ? C5 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C6 C5 C4 114.23(18) . . ? C6 C5 H5A 108.7 . . ? C4 C5 H5A 108.7 . . ? C6 C5 H5B 108.7 . . ? C4 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? C5 C6 C7 114.81(19) . . ? C5 C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? C5 C6 H6B 108.6 . . ? C7 C6 H6B 108.6 . . ? H6A C6 H6B 107.5 . . ? C8 C7 C6 115.02(19) . . ? C8 C7 H7A 108.5 . . ? C6 C7 H7A 108.5 . . ? C8 C7 H7B 108.5 . . ? C6 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? C9 C8 C7 114.37(18) . . ? C9 C8 H8A 108.7 . . ? C7 C8 H8A 108.7 . . ? C9 C8 H8B 108.7 . . ? C7 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? C8 C9 C10 115.91(19) . . ? C8 C9 H9A 108.3 . . ? C10 C9 H9A 108.3 . . ? C8 C9 H9B 108.3 . . ? C10 C9 H9B 108.3 . . ? H9A C9 H9B 107.4 . . ? C9 C10 C11 113.88(19) . . ? C9 C10 H10A 108.8 . . ? C11 C10 H10A 108.8 . . ? C9 C10 H10B 108.8 . . ? C11 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C10 C11 C12 113.54(16) . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C1 C12 C11 115.18(17) . . ? C1 C12 H12A 108.5 . . ? C11 C12 H12A 108.5 . . ? C1 C12 H12B 108.5 . . ? C11 C12 H12B 108.5 . . ? H12A C12 H12B 107.5 . . ? O2 C13 C14 112.50(13) . . ? O2 C13 C2 105.14(14) . . ? C14 C13 C2 111.70(14) . . ? O2 C13 H13 109.1 . . ? C14 C13 H13 109.1 . . ? C2 C13 H13 109.1 . . ? C15 C14 C19 117.90(17) . . ? C15 C14 C13 121.34(16) . . ? C19 C14 C13 120.75(16) . . ? C14 C15 C16 121.07(18) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C17 C16 C15 121.65(18) . . ? C17 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C16 C17 C18 117.13(17) . . ? C16 C17 C20 122.01(18) . . ? C18 C17 C20 120.85(19) . . ? C17 C18 C19 121.84(18) . . ? C17 C18 H18 119.1 . . ? C19 C18 H18 119.1 . . ? C14 C19 C18 120.38(17) . . ? C14 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C13 O2 H2O 104.1(17) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C13 118.87(18) . . . . ? C12 C1 C2 C13 -59.12(18) . . . . ? O1 C1 C2 C3 -115.94(18) . . . . ? C12 C1 C2 C3 66.07(19) . . . . ? C1 C2 C3 C4 65.11(19) . . . . ? C13 C2 C3 C4 -170.86(15) . . . . ? C2 C3 C4 C5 -169.74(17) . . . . ? C3 C4 C5 C6 72.8(2) . . . . ? C4 C5 C6 C7 71.7(2) . . . . ? C5 C6 C7 C8 -149.85(19) . . . . ? C6 C7 C8 C9 65.2(3) . . . . ? C7 C8 C9 C10 65.9(3) . . . . ? C8 C9 C10 C11 -169.28(18) . . . . ? C9 C10 C11 C12 69.8(2) . . . . ? O1 C1 C12 C11 27.9(2) . . . . ? C2 C1 C12 C11 -154.06(15) . . . . ? C10 C11 C12 C1 70.8(2) . . . . ? C1 C2 C13 O2 -49.23(17) . . . . ? C3 C2 C13 O2 -174.07(14) . . . . ? C1 C2 C13 C14 -171.54(14) . . . . ? C3 C2 C13 C14 63.63(18) . . . . ? O2 C13 C14 C15 128.80(16) . . . . ? C2 C13 C14 C15 -113.22(17) . . . . ? O2 C13 C14 C19 -52.1(2) . . . . ? C2 C13 C14 C19 65.87(19) . . . . ? C19 C14 C15 C16 -0.7(2) . . . . ? C13 C14 C15 C16 178.44(15) . . . . ? C14 C15 C16 C17 -0.5(3) . . . . ? C15 C16 C17 C18 1.4(3) . . . . ? C15 C16 C17 C20 -177.77(17) . . . . ? C16 C17 C18 C19 -1.2(3) . . . . ? C20 C17 C18 C19 178.02(17) . . . . ? C15 C14 C19 C18 0.9(2) . . . . ? C13 C14 C19 C18 -178.22(15) . . . . ? C17 C18 C19 C14 0.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.874 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.122 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.028 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2O O1 0.86(3) 2.04(3) 2.8659(19) 160(2) 2_646 C12 H12A O2 0.97 2.40 3.367(2) 174 2_646 C20 H20A Cg1 0.97 2.89 3.843(2) 173 2_556 #[ 2556] = -X,1/2+Y,1-Z # [ 2646. ] = 1-x,-1/2+y,1-z #6-Membered Ring ( 1) C(14) C(15) C(16) C(17) C(18) C(19) # Attachment '- 4h_deposit msc10_revised.cif' data_4h _database_code_depnum_ccdc_archive 'CCDC 843589' #TrackingRef '- 4h_deposit msc10_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-[(4-chlorophenyl)(hydroxy)methyl]cyclododecanone ; _chemical_name_common 2-((4-chlorophenyl)(hydroxy)methyl)cyclododecanone _chemical_melting_point ? _chemical_formula_moiety 'C19 H27 Cl O2' _chemical_formula_sum 'C19 H27 Cl O2' _chemical_formula_weight 322.86 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 12.5731(3) _cell_length_b 5.99250(10) _cell_length_c 23.9975(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.709(2) _cell_angle_gamma 90.00 _cell_volume 1748.82(6) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 15187 _cell_measurement_theta_min 2.6272 _cell_measurement_theta_max 29.2105 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.224 _exptl_absorpt_correction_T_min 0.86353 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(CrysAlis Pro; Oxford Diffraction, 2010)' _exptl_special_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur Eos Gemini' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 15.9821 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 36168 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 29.28 _reflns_number_total 4422 _reflns_number_gt 2967 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0619P)^2^+0.1253P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4422 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0720 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1204 _refine_ls_wR_factor_gt 0.1124 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.64902(4) 0.76816(9) 0.518574(18) 0.07054(17) Uani 1 1 d . . . O1 O 0.29349(9) 0.57965(19) 0.15325(5) 0.0596(3) Uani 1 1 d . . . O2 O 0.29599(8) 0.3870(2) 0.27942(5) 0.0527(3) Uani 1 1 d . . . H2O H 0.2800(19) 0.285(4) 0.3033(10) 0.103(8) Uiso 1 1 d . . . C1 C 0.36094(10) 0.4532(2) 0.18183(6) 0.0418(3) Uani 1 1 d . . . C2 C 0.43548(10) 0.5279(2) 0.23910(6) 0.0388(3) Uani 1 1 d . . . H2 H 0.4169 0.6832 0.2454 0.047 Uiso 1 1 calc R . . C3 C 0.55707(11) 0.5215(3) 0.23879(6) 0.0455(3) Uani 1 1 d . . . H3A H 0.6013 0.5534 0.2774 0.055 Uiso 1 1 calc R . . H3B H 0.5752 0.3718 0.2289 0.055 Uiso 1 1 calc R . . C4 C 0.58753(12) 0.6854(3) 0.19709(7) 0.0496(4) Uani 1 1 d . . . H4A H 0.5828 0.8359 0.2112 0.060 Uiso 1 1 calc R . . H4B H 0.5345 0.6726 0.1600 0.060 Uiso 1 1 calc R . . C5 C 0.70279(12) 0.6483(3) 0.18887(7) 0.0594(4) Uani 1 1 d . . . H5A H 0.7239 0.7795 0.1706 0.071 Uiso 1 1 calc R . . H5B H 0.7539 0.6338 0.2265 0.071 Uiso 1 1 calc R . . C6 C 0.71418(13) 0.4450(3) 0.15315(7) 0.0613(4) Uani 1 1 d . . . H6A H 0.6831 0.3170 0.1681 0.074 Uiso 1 1 calc R . . H6B H 0.7917 0.4154 0.1576 0.074 Uiso 1 1 calc R . . C7 C 0.65830(15) 0.4687(3) 0.08915(7) 0.0643(5) Uani 1 1 d . . . H7A H 0.5970 0.5710 0.0849 0.077 Uiso 1 1 calc R . . H7B H 0.7102 0.5355 0.0703 0.077 Uiso 1 1 calc R . . C8 C 0.61606(16) 0.2528(3) 0.05824(8) 0.0684(5) Uani 1 1 d . . . H8A H 0.5892 0.2838 0.0174 0.082 Uiso 1 1 calc R . . H8B H 0.6771 0.1495 0.0629 0.082 Uiso 1 1 calc R . . C9 C 0.52527(14) 0.1405(3) 0.07901(8) 0.0597(4) Uani 1 1 d . . . H9A H 0.5510 0.1168 0.1202 0.072 Uiso 1 1 calc R . . H9B H 0.5114 -0.0050 0.0609 0.072 Uiso 1 1 calc R . . C10 C 0.41721(14) 0.2683(3) 0.06697(7) 0.0587(4) Uani 1 1 d . . . H10A H 0.4327 0.4229 0.0781 0.070 Uiso 1 1 calc R . . H10B H 0.3836 0.2653 0.0259 0.070 Uiso 1 1 calc R . . C11 C 0.33564(13) 0.1771(3) 0.09823(7) 0.0617(5) Uani 1 1 d . . . H11A H 0.2647 0.2468 0.0825 0.074 Uiso 1 1 calc R . . H11B H 0.3271 0.0181 0.0909 0.074 Uiso 1 1 calc R . . C12 C 0.36934(13) 0.2154(3) 0.16278(7) 0.0504(4) Uani 1 1 d . . . H12A H 0.3238 0.1224 0.1804 0.060 Uiso 1 1 calc R . . H12B H 0.4448 0.1661 0.1773 0.060 Uiso 1 1 calc R . . C13 C 0.41205(10) 0.3876(2) 0.28819(6) 0.0402(3) Uani 1 1 d . . . H13 H 0.4371 0.2344 0.2850 0.048 Uiso 1 1 calc R . . C14 C 0.47009(10) 0.4792(2) 0.34662(6) 0.0388(3) Uani 1 1 d . . . C15 C 0.55346(11) 0.3623(3) 0.38387(6) 0.0453(3) Uani 1 1 d . . . H15 H 0.5735 0.2227 0.3729 0.054 Uiso 1 1 calc R . . C16 C 0.60783(12) 0.4479(3) 0.43702(6) 0.0518(4) Uani 1 1 d . . . H16 H 0.6631 0.3663 0.4618 0.062 Uiso 1 1 calc R . . C17 C 0.57898(11) 0.6551(3) 0.45272(6) 0.0464(3) Uani 1 1 d . . . C18 C 0.49534(12) 0.7746(3) 0.41694(7) 0.0501(4) Uani 1 1 d . . . H18 H 0.4752 0.9134 0.4283 0.060 Uiso 1 1 calc R . . C19 C 0.44168(11) 0.6866(3) 0.36423(6) 0.0473(4) Uani 1 1 d . . . H19 H 0.3854 0.7676 0.3400 0.057 Uiso 1 1 calc 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 Cl1 0.0660(3) 0.0899(4) 0.0525(2) -0.0158(2) 0.0090(2) 0.0078(2) O1 0.0545(6) 0.0651(8) 0.0526(6) 0.0019(5) 0.0013(5) 0.0181(6) O2 0.0381(5) 0.0619(7) 0.0600(7) 0.0041(6) 0.0162(5) -0.0048(5) C1 0.0338(7) 0.0493(8) 0.0441(7) 0.0036(6) 0.0131(6) 0.0002(6) C2 0.0358(7) 0.0373(7) 0.0435(7) 0.0033(6) 0.0102(5) 0.0024(6) C3 0.0360(7) 0.0538(9) 0.0455(7) 0.0087(7) 0.0083(5) -0.0020(6) C4 0.0491(8) 0.0507(9) 0.0496(8) 0.0056(7) 0.0135(7) -0.0093(7) C5 0.0471(8) 0.0779(12) 0.0524(9) 0.0052(8) 0.0108(7) -0.0214(8) C6 0.0528(9) 0.0812(13) 0.0532(9) 0.0107(9) 0.0194(7) 0.0006(8) C7 0.0760(11) 0.0732(12) 0.0480(9) 0.0108(8) 0.0238(8) -0.0134(9) C8 0.0783(12) 0.0768(13) 0.0594(10) 0.0001(9) 0.0346(9) -0.0029(10) C9 0.0730(11) 0.0511(10) 0.0606(10) -0.0018(8) 0.0272(8) -0.0005(8) C10 0.0686(10) 0.0638(11) 0.0402(8) -0.0014(7) 0.0075(7) -0.0013(8) C11 0.0522(9) 0.0689(11) 0.0603(10) -0.0181(9) 0.0076(8) -0.0131(8) C12 0.0496(8) 0.0484(9) 0.0563(9) -0.0017(7) 0.0191(7) -0.0063(7) C13 0.0357(7) 0.0394(8) 0.0471(7) 0.0041(6) 0.0133(6) 0.0024(6) C14 0.0362(6) 0.0400(8) 0.0442(7) 0.0067(6) 0.0172(5) 0.0014(6) C15 0.0485(8) 0.0405(8) 0.0492(8) 0.0057(6) 0.0166(6) 0.0107(6) C16 0.0480(8) 0.0590(10) 0.0470(8) 0.0096(7) 0.0093(6) 0.0154(7) C17 0.0417(7) 0.0574(9) 0.0425(7) -0.0002(7) 0.0153(6) 0.0022(7) C18 0.0519(8) 0.0444(9) 0.0573(9) -0.0038(7) 0.0199(7) 0.0077(7) C19 0.0409(7) 0.0462(8) 0.0542(9) 0.0052(7) 0.0111(6) 0.0121(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C17 1.7394(15) . ? O1 C1 1.2117(16) . ? O2 C13 1.4204(16) . ? O2 H2O 0.90(2) . ? C1 C12 1.508(2) . ? C1 C2 1.5211(19) . ? C2 C3 1.5312(18) . ? C2 C13 1.5356(19) . ? C2 H2 0.9800 . ? C3 C4 1.519(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.528(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.518(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.525(2) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.519(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.514(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.522(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.518(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.516(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.5101(19) . ? C13 H13 0.9800 . ? C14 C15 1.3832(19) . ? C14 C19 1.388(2) . ? C15 C16 1.384(2) . ? C15 H15 0.9300 . ? C16 C17 1.373(2) . ? C16 H16 0.9300 . ? C17 C18 1.377(2) . ? C18 C19 1.378(2) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O2 H2O 107.3(15) . . ? O1 C1 C12 120.80(13) . . ? O1 C1 C2 120.62(13) . . ? C12 C1 C2 118.52(12) . . ? C1 C2 C3 112.03(11) . . ? C1 C2 C13 109.74(11) . . ? C3 C2 C13 112.10(11) . . ? C1 C2 H2 107.6 . . ? C3 C2 H2 107.6 . . ? C13 C2 H2 107.6 . . ? C4 C3 C2 113.94(12) . . ? C4 C3 H3A 108.8 . . ? C2 C3 H3A 108.8 . . ? C4 C3 H3B 108.8 . . ? C2 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C3 C4 C5 113.40(13) . . ? C3 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? C3 C4 H4B 108.9 . . ? C5 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C6 C5 C4 114.73(13) . . ? C6 C5 H5A 108.6 . . ? C4 C5 H5A 108.6 . . ? C6 C5 H5B 108.6 . . ? C4 C5 H5B 108.6 . . ? H5A C5 H5B 107.6 . . ? C5 C6 C7 114.11(15) . . ? C5 C6 H6A 108.7 . . ? C7 C6 H6A 108.7 . . ? C5 C6 H6B 108.7 . . ? C7 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C8 C7 C6 115.27(16) . . ? C8 C7 H7A 108.5 . . ? C6 C7 H7A 108.5 . . ? C8 C7 H7B 108.5 . . ? C6 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? C9 C8 C7 114.66(14) . . ? C9 C8 H8A 108.6 . . ? C7 C8 H8A 108.6 . . ? C9 C8 H8B 108.6 . . ? C7 C8 H8B 108.6 . . ? H8A C8 H8B 107.6 . . ? C8 C9 C10 115.16(15) . . ? C8 C9 H9A 108.5 . . ? C10 C9 H9A 108.5 . . ? C8 C9 H9B 108.5 . . ? C10 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? C11 C10 C9 114.06(15) . . ? C11 C10 H10A 108.7 . . ? C9 C10 H10A 108.7 . . ? C11 C10 H10B 108.7 . . ? C9 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C12 C11 C10 113.69(13) . . ? C12 C11 H11A 108.8 . . ? C10 C11 H11A 108.8 . . ? C12 C11 H11B 108.8 . . ? C10 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? C1 C12 C11 115.46(14) . . ? C1 C12 H12A 108.4 . . ? C11 C12 H12A 108.4 . . ? C1 C12 H12B 108.4 . . ? C11 C12 H12B 108.4 . . ? H12A C12 H12B 107.5 . . ? O2 C13 C14 112.00(11) . . ? O2 C13 C2 106.13(11) . . ? C14 C13 C2 111.82(11) . . ? O2 C13 H13 108.9 . . ? C14 C13 H13 108.9 . . ? C2 C13 H13 108.9 . . ? C15 C14 C19 117.93(13) . . ? C15 C14 C13 121.60(13) . . ? C19 C14 C13 120.47(12) . . ? C14 C15 C16 121.57(14) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C17 C16 C15 119.03(13) . . ? C17 C16 H16 120.5 . . ? C15 C16 H16 120.5 . . ? C16 C17 C18 120.82(14) . . ? C16 C17 Cl1 119.57(11) . . ? C18 C17 Cl1 119.62(12) . . ? C17 C18 C19 119.44(14) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? C18 C19 C14 121.20(13) . . ? C18 C19 H19 119.4 . . ? C14 C19 H19 119.4 . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -118.30(14) . . . . ? C12 C1 C2 C3 64.45(16) . . . . ? O1 C1 C2 C13 116.51(15) . . . . ? C12 C1 C2 C13 -60.75(15) . . . . ? C1 C2 C3 C4 65.11(17) . . . . ? C13 C2 C3 C4 -171.00(12) . . . . ? C2 C3 C4 C5 -169.31(13) . . . . ? C3 C4 C5 C6 73.45(18) . . . . ? C4 C5 C6 C7 71.42(18) . . . . ? C5 C6 C7 C8 -149.92(15) . . . . ? C6 C7 C8 C9 64.2(2) . . . . ? C7 C8 C9 C10 66.4(2) . . . . ? C8 C9 C10 C11 -168.44(14) . . . . ? C9 C10 C11 C12 70.0(2) . . . . ? O1 C1 C12 C11 29.1(2) . . . . ? C2 C1 C12 C11 -153.62(12) . . . . ? C10 C11 C12 C1 72.04(19) . . . . ? C1 C2 C13 O2 -48.21(14) . . . . ? C3 C2 C13 O2 -173.36(11) . . . . ? C1 C2 C13 C14 -170.61(11) . . . . ? C3 C2 C13 C14 64.24(15) . . . . ? O2 C13 C14 C15 127.40(13) . . . . ? C2 C13 C14 C15 -113.62(14) . . . . ? O2 C13 C14 C19 -53.39(17) . . . . ? C2 C13 C14 C19 65.59(16) . . . . ? C19 C14 C15 C16 -0.3(2) . . . . ? C13 C14 C15 C16 178.93(13) . . . . ? C14 C15 C16 C17 -0.8(2) . . . . ? C15 C16 C17 C18 1.6(2) . . . . ? C15 C16 C17 Cl1 -178.31(11) . . . . ? C16 C17 C18 C19 -1.4(2) . . . . ? Cl1 C17 C18 C19 178.55(11) . . . . ? C17 C18 C19 C14 0.3(2) . . . . ? C15 C14 C19 C18 0.6(2) . . . . ? C13 C14 C19 C18 -178.68(13) . . . . ? _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.348 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.033 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2O O1 0.90(2) 1.99(2) 2.8621(16) 166(2) 2_545 C12 H12A O2 0.97 2.43 3.403(2) 178 2_545 # [ 2545. ] = 1/2-x,-1/2+y,1/2-z # Attachment '- 4i_deposit_msc12 corrected_revised.cif' data_4i _database_code_depnum_ccdc_archive 'CCDC 843590' #TrackingRef '- 4i_deposit_msc12 corrected_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-[(4-bromophenyl)(hydroxy)methyl]cyclododecanone ; _chemical_name_common 2-((4-bromophenyl)(hydroxy)methyl)cyclododecanone _chemical_melting_point ? _chemical_formula_moiety 'C19 H27 Br O2' _chemical_formula_sum 'C19 H27 Br O2' _chemical_formula_weight 367.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y+1/2, z+1/2' _cell_length_a 12.5505(8) _cell_length_b 6.0048(5) _cell_length_c 24.4004(15) _cell_angle_alpha 90.00 _cell_angle_beta 104.889(7) _cell_angle_gamma 90.00 _cell_volume 1777.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 7291 _cell_measurement_theta_min 2.6951 _cell_measurement_theta_max 29.3081 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 2.318 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.67367 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details '(CrysAlis Pro; Oxford Diffraction, 2010)' _exptl_special_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur Eos Gemini' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 15.9821 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 25143 _diffrn_reflns_av_R_equivalents 0.0453 _diffrn_reflns_av_sigmaI/netI 0.0592 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 29.36 _reflns_number_total 4476 _reflns_number_gt 2396 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0378P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4476 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0788 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0703 _refine_ls_wR_factor_gt 0.0655 _refine_ls_goodness_of_fit_ref 0.850 _refine_ls_restrained_S_all 0.850 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.82187(13) 0.5440(3) 0.18182(7) 0.0393(4) Uani 1 1 d . . . C2 C 0.80339(13) 0.4698(3) 0.23824(6) 0.0368(4) Uani 1 1 d . . . H2 H 0.8285 0.3152 0.2445 0.044 Uiso 1 1 calc R . . C3 C 0.68154(13) 0.4751(3) 0.23813(7) 0.0439(4) Uani 1 1 d . . . H3A H 0.6753 0.4423 0.2761 0.053 Uiso 1 1 calc R . . H3B H 0.6535 0.6244 0.2286 0.053 Uiso 1 1 calc R . . C4 C 0.61019(14) 0.3123(3) 0.19708(8) 0.0490(5) Uani 1 1 d . . . H4A H 0.6281 0.1622 0.2111 0.059 Uiso 1 1 calc R . . H4B H 0.6278 0.3242 0.1607 0.059 Uiso 1 1 calc R . . C5 C 0.48684(15) 0.3501(4) 0.18832(8) 0.0603(6) Uani 1 1 d . . . H5A H 0.4478 0.2192 0.1703 0.072 Uiso 1 1 calc R . . H5B H 0.4716 0.3658 0.2251 0.072 Uiso 1 1 calc R . . C6 C 0.44197(16) 0.5512(4) 0.15293(8) 0.0627(6) Uani 1 1 d . . . H6A H 0.4878 0.6788 0.1677 0.075 Uiso 1 1 calc R . . H6B H 0.3683 0.5818 0.1568 0.075 Uiso 1 1 calc R . . C7 C 0.43686(17) 0.5250(4) 0.08974(8) 0.0655(6) Uani 1 1 d . . . H7A H 0.4953 0.4249 0.0861 0.079 Uiso 1 1 calc R . . H7B H 0.3673 0.4556 0.0710 0.079 Uiso 1 1 calc R . . C8 C 0.44771(18) 0.7409(4) 0.05914(10) 0.0715(7) Uani 1 1 d . . . H8A H 0.4345 0.7098 0.0189 0.086 Uiso 1 1 calc R . . H8B H 0.3908 0.8430 0.0639 0.086 Uiso 1 1 calc R . . C9 C 0.55862(16) 0.8547(3) 0.07927(9) 0.0599(6) Uani 1 1 d . . . H9A H 0.5546 0.9984 0.0606 0.072 Uiso 1 1 calc R . . H9B H 0.5725 0.8820 0.1197 0.072 Uiso 1 1 calc R . . C10 C 0.65552(16) 0.7276(3) 0.06867(8) 0.0594(6) Uani 1 1 d . . . H10A H 0.6502 0.7289 0.0283 0.071 Uiso 1 1 calc R . . H10B H 0.6508 0.5738 0.0800 0.071 Uiso 1 1 calc R . . C11 C 0.76741(16) 0.8202(4) 0.10003(8) 0.0601(6) Uani 1 1 d . . . H11A H 0.8238 0.7520 0.0848 0.072 Uiso 1 1 calc R . . H11B H 0.7684 0.9791 0.0931 0.072 Uiso 1 1 calc R . . C12 C 0.79529(16) 0.7803(3) 0.16340(8) 0.0493(5) Uani 1 1 d . . . H12A H 0.8579 0.8729 0.1812 0.059 Uiso 1 1 calc R . . H12B H 0.7334 0.8289 0.1774 0.059 Uiso 1 1 calc R . . C13 C 0.87438(13) 0.6102(3) 0.28676(7) 0.0394(4) Uani 1 1 d . . . H13 H 0.8459 0.7629 0.2836 0.047 Uiso 1 1 calc R . . C14 C 0.87354(13) 0.5186(3) 0.34416(7) 0.0370(4) Uani 1 1 d . . . C15 C 0.82780(14) 0.6363(3) 0.38121(8) 0.0454(5) Uani 1 1 d . . . H15 H 0.7976 0.7762 0.3707 0.054 Uiso 1 1 calc R . . C16 C 0.82598(14) 0.5502(3) 0.43362(8) 0.0499(5) Uani 1 1 d . . . H16 H 0.7952 0.6315 0.4582 0.060 Uiso 1 1 calc R . . C17 C 0.87007(13) 0.3440(3) 0.44881(7) 0.0434(5) Uani 1 1 d . . . C18 C 0.91702(14) 0.2237(3) 0.41291(8) 0.0487(5) Uani 1 1 d . . . H18 H 0.9473 0.0841 0.4237 0.058 Uiso 1 1 calc R . . C19 C 0.91881(14) 0.3117(3) 0.36088(8) 0.0448(5) Uani 1 1 d . . . H19 H 0.9509 0.2309 0.3368 0.054 Uiso 1 1 calc R . . O1 O 0.86210(10) 0.4179(2) 0.15374(5) 0.0567(4) Uani 1 1 d . . . O2 O 0.98179(10) 0.6114(2) 0.27787(6) 0.0507(4) Uani 1 1 d . . . Br1 Br 0.865385(18) 0.21877(4) 0.519587(8) 0.06551(11) Uani 1 1 d . . . H2O H 1.0149(18) 0.708(3) 0.2988(9) 0.072(8) Uiso 1 1 d . . . 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 0.0292(9) 0.0441(12) 0.0440(10) -0.0034(9) 0.0080(8) -0.0033(8) C2 0.0330(9) 0.0344(10) 0.0432(10) -0.0036(8) 0.0103(7) 0.0005(8) C3 0.0387(10) 0.0523(12) 0.0425(10) -0.0057(9) 0.0137(8) -0.0074(9) C4 0.0485(11) 0.0476(12) 0.0507(11) -0.0020(10) 0.0122(9) -0.0130(9) C5 0.0464(12) 0.0811(16) 0.0548(12) -0.0062(12) 0.0154(10) -0.0223(12) C6 0.0439(12) 0.0840(17) 0.0569(13) -0.0083(12) 0.0071(10) -0.0039(11) C7 0.0598(14) 0.0768(17) 0.0510(12) -0.0067(12) -0.0022(10) -0.0172(12) C8 0.0611(14) 0.0777(17) 0.0635(13) -0.0049(13) -0.0064(11) 0.0009(12) C9 0.0594(13) 0.0481(13) 0.0658(13) 0.0016(11) 0.0042(10) 0.0021(11) C10 0.0710(15) 0.0678(15) 0.0383(10) -0.0010(10) 0.0119(10) -0.0015(12) C11 0.0566(13) 0.0648(15) 0.0637(13) 0.0152(11) 0.0243(11) -0.0032(11) C12 0.0423(11) 0.0473(12) 0.0568(12) 0.0016(10) 0.0099(9) -0.0050(9) C13 0.0321(10) 0.0386(11) 0.0468(10) -0.0032(9) 0.0090(8) 0.0013(8) C14 0.0277(9) 0.0390(11) 0.0428(10) -0.0064(9) 0.0062(7) -0.0011(8) C15 0.0443(11) 0.0379(11) 0.0511(11) -0.0045(9) 0.0073(9) 0.0091(9) C16 0.0490(12) 0.0533(13) 0.0478(11) -0.0097(10) 0.0135(9) 0.0100(10) C17 0.0333(10) 0.0537(13) 0.0418(10) -0.0016(9) 0.0070(8) 0.0028(9) C18 0.0419(11) 0.0441(12) 0.0582(12) 0.0045(10) 0.0095(9) 0.0115(9) C19 0.0420(10) 0.0441(12) 0.0503(11) -0.0028(9) 0.0158(9) 0.0109(9) O1 0.0647(9) 0.0604(9) 0.0501(8) -0.0046(7) 0.0239(7) 0.0130(7) O2 0.0343(8) 0.0586(9) 0.0604(9) -0.0051(8) 0.0142(6) -0.0068(7) Br1 0.06340(16) 0.08402(19) 0.05018(13) 0.01294(12) 0.01655(10) 0.01479(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.2147(19) . ? C1 C12 1.500(3) . ? C1 C2 1.520(2) . ? C2 C3 1.529(2) . ? C2 C13 1.538(2) . ? C2 H2 0.9800 . ? C3 C4 1.516(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.524(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.507(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.535(2) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.519(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.515(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.513(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.521(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.514(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 O2 1.4194(19) . ? C13 C14 1.507(2) . ? C13 H13 0.9800 . ? C14 C15 1.383(2) . ? C14 C19 1.383(2) . ? C15 C16 1.385(2) . ? C15 H15 0.9300 . ? C16 C17 1.368(3) . ? C16 H16 0.9300 . ? C17 C18 1.379(3) . ? C17 Br1 1.8982(18) . ? C18 C19 1.381(2) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? O2 H2O 0.81(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C12 120.87(16) . . ? O1 C1 C2 120.70(16) . . ? C12 C1 C2 118.34(16) . . ? C1 C2 C3 112.20(13) . . ? C1 C2 C13 110.09(14) . . ? C3 C2 C13 111.81(13) . . ? C1 C2 H2 107.5 . . ? C3 C2 H2 107.5 . . ? C13 C2 H2 107.5 . . ? C4 C3 C2 114.12(14) . . ? C4 C3 H3A 108.7 . . ? C2 C3 H3A 108.7 . . ? C4 C3 H3B 108.7 . . ? C2 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? C3 C4 C5 113.76(16) . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4B 108.8 . . ? C5 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C6 C5 C4 114.59(17) . . ? C6 C5 H5A 108.6 . . ? C4 C5 H5A 108.6 . . ? C6 C5 H5B 108.6 . . ? C4 C5 H5B 108.6 . . ? H5A C5 H5B 107.6 . . ? C5 C6 C7 113.98(18) . . ? C5 C6 H6A 108.8 . . ? C7 C6 H6A 108.8 . . ? C5 C6 H6B 108.8 . . ? C7 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C8 C7 C6 114.85(19) . . ? C8 C7 H7A 108.6 . . ? C6 C7 H7A 108.6 . . ? C8 C7 H7B 108.6 . . ? C6 C7 H7B 108.6 . . ? H7A C7 H7B 107.5 . . ? C9 C8 C7 114.62(17) . . ? C9 C8 H8A 108.6 . . ? C7 C8 H8A 108.6 . . ? C9 C8 H8B 108.6 . . ? C7 C8 H8B 108.6 . . ? H8A C8 H8B 107.6 . . ? C10 C9 C8 115.39(18) . . ? C10 C9 H9A 108.4 . . ? C8 C9 H9A 108.4 . . ? C10 C9 H9B 108.4 . . ? C8 C9 H9B 108.4 . . ? H9A C9 H9B 107.5 . . ? C9 C10 C11 114.09(17) . . ? C9 C10 H10A 108.7 . . ? C11 C10 H10A 108.7 . . ? C9 C10 H10B 108.7 . . ? C11 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C12 C11 C10 113.41(15) . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11B 108.9 . . ? C10 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C1 C12 C11 115.52(16) . . ? C1 C12 H12A 108.4 . . ? C11 C12 H12A 108.4 . . ? C1 C12 H12B 108.4 . . ? C11 C12 H12B 108.4 . . ? H12A C12 H12B 107.5 . . ? O2 C13 C14 112.19(13) . . ? O2 C13 C2 105.68(13) . . ? C14 C13 C2 111.98(14) . . ? O2 C13 H13 109.0 . . ? C14 C13 H13 109.0 . . ? C2 C13 H13 109.0 . . ? C15 C14 C19 118.31(16) . . ? C15 C14 C13 121.60(16) . . ? C19 C14 C13 120.09(15) . . ? C14 C15 C16 121.38(17) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C17 C16 C15 119.12(17) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C16 C17 C18 120.73(17) . . ? C16 C17 Br1 120.01(14) . . ? C18 C17 Br1 119.26(14) . . ? C17 C18 C19 119.63(17) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C18 C19 C14 120.82(17) . . ? C18 C19 H19 119.6 . . ? C14 C19 H19 119.6 . . ? C13 O2 H2O 105.0(16) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -118.47(18) . . . . ? C12 C1 C2 C3 65.0(2) . . . . ? O1 C1 C2 C13 116.32(18) . . . . ? C12 C1 C2 C13 -60.21(19) . . . . ? C1 C2 C3 C4 64.6(2) . . . . ? C13 C2 C3 C4 -171.12(15) . . . . ? C2 C3 C4 C5 -168.29(16) . . . . ? C3 C4 C5 C6 73.6(2) . . . . ? C4 C5 C6 C7 71.4(2) . . . . ? C5 C6 C7 C8 -151.26(18) . . . . ? C6 C7 C8 C9 65.3(3) . . . . ? C7 C8 C9 C10 65.0(3) . . . . ? C8 C9 C10 C11 -167.60(17) . . . . ? C9 C10 C11 C12 71.1(2) . . . . ? O1 C1 C12 C11 28.9(2) . . . . ? C2 C1 C12 C11 -154.59(15) . . . . ? C10 C11 C12 C1 71.7(2) . . . . ? C1 C2 C13 O2 -48.03(18) . . . . ? C3 C2 C13 O2 -173.46(14) . . . . ? C1 C2 C13 C14 -170.46(14) . . . . ? C3 C2 C13 C14 64.11(19) . . . . ? O2 C13 C14 C15 126.53(17) . . . . ? C2 C13 C14 C15 -114.83(17) . . . . ? O2 C13 C14 C19 -53.7(2) . . . . ? C2 C13 C14 C19 64.9(2) . . . . ? C19 C14 C15 C16 -0.6(3) . . . . ? C13 C14 C15 C16 179.17(16) . . . . ? C14 C15 C16 C17 -0.2(3) . . . . ? C15 C16 C17 C18 0.8(3) . . . . ? C15 C16 C17 Br1 -178.43(13) . . . . ? C16 C17 C18 C19 -0.5(3) . . . . ? Br1 C17 C18 C19 178.73(13) . . . . ? C17 C18 C19 C14 -0.4(3) . . . . ? C15 C14 C19 C18 0.9(3) . . . . ? C13 C14 C19 C18 -178.88(16) . . . . ? _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.351 _refine_diff_density_min -0.612 _refine_diff_density_rms 0.051 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2O O1 0.81(2) 2.10(2) 2.8863(18) 164(2) 2_755 C12 H12A O2 0.97 2.46 3.431(2) 177 2_755 # [ 2755. ] = 2-x,1/2+y,1/2-z #6-Membered Ring ( 1) C(14) C(15) C(16) C(17) C(18) C(19) # Attachment '- 4j_deposit vit-msc17_revised.cif' data_4j _database_code_depnum_ccdc_archive 'CCDC 843591' #TrackingRef '- 4j_deposit vit-msc17_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-[(4-ethylphenyl)(hydroxy)methyl]cyclododecanone ; _chemical_name_common 2-((4-ethylphenyl)(hydroxy)methyl)cyclododecanone _chemical_melting_point ? _chemical_formula_moiety 'C21 H32 O2' _chemical_formula_sum 'C21 H32 O2' _chemical_formula_weight 316.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y+1/2, z+1/2' _cell_length_a 12.665(14) _cell_length_b 5.8290(18) _cell_length_c 25.713(9) _cell_angle_alpha 90.00 _cell_angle_beta 100.94(5) _cell_angle_gamma 90.00 _cell_volume 1864(2) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 1827 _cell_measurement_theta_min 2.6473 _cell_measurement_theta_max 29.1484 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.128 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_T_min 0.36989 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(CrysAlis Pro; Oxford Diffraction, 2010)' _exptl_special_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur Eos Gemini' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 15.9821 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 7045 _diffrn_reflns_av_R_equivalents 0.0586 _diffrn_reflns_av_sigmaI/netI 0.0664 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3659 _reflns_number_gt 2320 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0984P)^2^+0.1388P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3659 _refine_ls_number_parameters 213 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1003 _refine_ls_R_factor_gt 0.0676 _refine_ls_wR_factor_ref 0.2113 _refine_ls_wR_factor_gt 0.1733 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.32845(17) 0.5294(4) 0.18377(8) 0.0463(5) Uani 1 1 d . . . C2 C 0.29933(17) 0.4617(4) 0.23631(8) 0.0433(5) Uani 1 1 d . . . H2 H 0.3201 0.3008 0.2427 0.052 Uiso 1 1 calc R . . C3 C 0.17945(18) 0.4764(4) 0.23497(8) 0.0515(6) Uani 1 1 d . . . H3A H 0.1557 0.6317 0.2255 0.062 Uiso 1 1 calc R . . H3B H 0.1662 0.4464 0.2703 0.062 Uiso 1 1 calc R . . C4 C 0.1124(2) 0.3115(4) 0.19658(9) 0.0567(6) Uani 1 1 d . . . H4A H 0.1241 0.1570 0.2105 0.068 Uiso 1 1 calc R . . H4B H 0.1374 0.3165 0.1632 0.068 Uiso 1 1 calc R . . C5 C -0.0072(2) 0.3618(5) 0.18621(11) 0.0736(8) Uani 1 1 d . . . H5A H -0.0455 0.2274 0.1703 0.088 Uiso 1 1 calc R . . H5B H -0.0292 0.3887 0.2198 0.088 Uiso 1 1 calc R . . C6 C -0.0403(2) 0.5657(5) 0.15059(11) 0.0752(8) Uani 1 1 d . . . H6A H 0.0056 0.6944 0.1637 0.090 Uiso 1 1 calc R . . H6B H -0.1134 0.6073 0.1529 0.090 Uiso 1 1 calc R . . C7 C -0.0347(2) 0.5273(5) 0.09227(10) 0.0752(8) Uani 1 1 d . . . H7A H 0.0225 0.4187 0.0905 0.090 Uiso 1 1 calc R . . H7B H -0.1016 0.4576 0.0748 0.090 Uiso 1 1 calc R . . C8 C -0.0154(2) 0.7409(5) 0.06164(11) 0.0797(9) Uani 1 1 d . . . H8A H -0.0216 0.7003 0.0246 0.096 Uiso 1 1 calc R . . H8B H -0.0716 0.8513 0.0641 0.096 Uiso 1 1 calc R . . C9 C 0.0924(2) 0.8540(5) 0.08040(11) 0.0722(8) Uani 1 1 d . . . H9A H 0.0939 0.9965 0.0611 0.087 Uiso 1 1 calc R . . H9B H 0.0986 0.8925 0.1176 0.087 Uiso 1 1 calc R . . C10 C 0.1891(2) 0.7130(5) 0.07411(9) 0.0636(7) Uani 1 1 d . . . H10A H 0.1934 0.7077 0.0369 0.076 Uiso 1 1 calc R . . H10B H 0.1790 0.5572 0.0855 0.076 Uiso 1 1 calc R . . C11 C 0.2942(2) 0.8039(5) 0.10507(9) 0.0641(7) Uani 1 1 d . . . H11A H 0.2990 0.9664 0.0977 0.077 Uiso 1 1 calc R . . H11B H 0.3530 0.7278 0.0927 0.077 Uiso 1 1 calc R . . C12 C 0.3085(2) 0.7710(4) 0.16475(8) 0.0549(6) Uani 1 1 d . . . H12A H 0.3684 0.8651 0.1818 0.066 Uiso 1 1 calc R . . H12B H 0.2445 0.8269 0.1762 0.066 Uiso 1 1 calc R . . C13 C 0.36535(16) 0.6022(4) 0.28140(8) 0.0448(5) Uani 1 1 d . . . H13 H 0.3401 0.7614 0.2783 0.054 Uiso 1 1 calc R . . C14 C 0.35471(16) 0.5119(4) 0.33516(7) 0.0412(5) Uani 1 1 d . . . C15 C 0.30003(18) 0.6327(4) 0.36781(8) 0.0528(6) Uani 1 1 d . . . H15 H 0.2701 0.7746 0.3570 0.063 Uiso 1 1 calc R . . C16 C 0.2890(2) 0.5440(5) 0.41729(9) 0.0614(7) Uani 1 1 d . . . H16 H 0.2523 0.6292 0.4387 0.074 Uiso 1 1 calc R . . C17 C 0.33078(19) 0.3365(5) 0.43463(9) 0.0607(7) Uani 1 1 d . . . C18 C 0.3859(2) 0.2172(4) 0.40172(9) 0.0597(7) Uani 1 1 d . . . H18 H 0.4163 0.0760 0.4128 0.072 Uiso 1 1 calc R . . C19 C 0.39719(18) 0.3017(4) 0.35281(8) 0.0512(6) Uani 1 1 d . . . H19 H 0.4339 0.2156 0.3315 0.061 Uiso 1 1 calc R . . C20 C 0.3219(3) 0.2402(6) 0.48854(10) 0.0841(9) Uani 1 1 d . . . H20A H 0.2630 0.3163 0.5008 0.101 Uiso 1 1 calc R . . H20B H 0.3044 0.0784 0.4847 0.101 Uiso 1 1 calc R . . C21 C 0.4202(2) 0.2669(6) 0.52907(10) 0.0839(10) Uani 1 1 d . . . H21A H 0.4800 0.2006 0.5165 0.126 Uiso 1 1 calc R . . H21B H 0.4110 0.1905 0.5610 0.126 Uiso 1 1 calc R . . H21C H 0.4336 0.4270 0.5362 0.126 Uiso 1 1 calc R . . O1 O 0.37152(15) 0.3934(3) 0.15929(6) 0.0702(6) Uani 1 1 d . . . O2 O 0.47300(13) 0.5963(3) 0.27406(7) 0.0611(5) Uani 1 1 d . . . H2O H 0.510(4) 0.707(7) 0.2945(19) 0.19(2) Uiso 1 1 d . . . 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 0.0467(12) 0.0516(13) 0.0387(10) 0.0000(10) 0.0030(9) 0.0023(11) C2 0.0479(12) 0.0414(11) 0.0384(10) -0.0013(9) 0.0026(9) 0.0009(10) C3 0.0513(13) 0.0591(14) 0.0419(11) -0.0053(11) 0.0031(10) -0.0046(11) C4 0.0585(14) 0.0538(14) 0.0538(13) -0.0022(11) 0.0004(11) -0.0126(12) C5 0.0604(16) 0.088(2) 0.0689(17) -0.0010(16) 0.0045(13) -0.0238(15) C6 0.0540(15) 0.094(2) 0.0722(17) -0.0030(16) -0.0022(13) 0.0045(15) C7 0.0690(17) 0.084(2) 0.0608(15) -0.0079(15) -0.0173(13) -0.0073(16) C8 0.0725(18) 0.085(2) 0.0713(18) -0.0018(17) -0.0136(14) 0.0135(16) C9 0.0763(18) 0.0594(16) 0.0739(17) 0.0032(14) -0.0036(14) 0.0091(15) C10 0.0778(18) 0.0695(16) 0.0413(12) 0.0016(12) 0.0059(12) 0.0081(14) C11 0.0714(17) 0.0652(16) 0.0572(14) 0.0182(12) 0.0160(13) 0.0013(14) C12 0.0605(14) 0.0489(13) 0.0524(13) 0.0034(11) 0.0031(11) -0.0041(12) C13 0.0432(11) 0.0441(12) 0.0445(11) -0.0027(10) 0.0019(9) 0.0000(10) C14 0.0397(11) 0.0424(11) 0.0376(10) -0.0051(9) -0.0027(9) -0.0015(9) C15 0.0512(13) 0.0517(13) 0.0512(13) -0.0105(11) -0.0009(10) 0.0075(11) C16 0.0581(14) 0.0794(18) 0.0458(12) -0.0147(13) 0.0078(11) 0.0012(14) C17 0.0502(13) 0.0835(18) 0.0430(12) 0.0019(13) -0.0049(11) -0.0090(14) C18 0.0623(15) 0.0595(15) 0.0502(13) 0.0091(12) -0.0073(12) 0.0013(13) C19 0.0546(13) 0.0511(14) 0.0449(12) -0.0026(10) 0.0017(10) 0.0063(11) C20 0.0769(19) 0.120(3) 0.0531(15) 0.0107(16) 0.0055(14) -0.0231(19) C21 0.093(2) 0.112(3) 0.0468(14) 0.0117(15) 0.0132(15) 0.0256(19) O1 0.0913(13) 0.0713(12) 0.0523(10) 0.0018(9) 0.0242(10) 0.0243(10) O2 0.0487(9) 0.0712(12) 0.0615(10) -0.0016(9) 0.0052(8) -0.0093(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.205(2) . ? C1 C12 1.496(3) . ? C1 C2 1.518(3) . ? C2 C3 1.514(3) . ? C2 C13 1.532(3) . ? C2 H2 0.9800 . ? C3 C4 1.517(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.517(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.510(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.531(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.518(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.510(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.509(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.512(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.523(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 O2 1.412(3) . ? C13 C14 1.509(3) . ? C13 H13 0.9800 . ? C14 C15 1.379(3) . ? C14 C19 1.380(3) . ? C15 C16 1.405(3) . ? C15 H15 0.9300 . ? C16 C17 1.361(4) . ? C16 H16 0.9300 . ? C17 C18 1.382(3) . ? C17 C20 1.519(3) . ? C18 C19 1.383(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.472(4) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? O2 H2O 0.91(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C12 120.9(2) . . ? O1 C1 C2 120.3(2) . . ? C12 C1 C2 118.75(19) . . ? C3 C2 C1 112.14(18) . . ? C3 C2 C13 112.83(17) . . ? C1 C2 C13 110.18(17) . . ? C3 C2 H2 107.1 . . ? C1 C2 H2 107.1 . . ? C13 C2 H2 107.1 . . ? C2 C3 C4 114.44(19) . . ? C2 C3 H3A 108.7 . . ? C4 C3 H3A 108.7 . . ? C2 C3 H3B 108.7 . . ? C4 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? C3 C4 C5 114.1(2) . . ? C3 C4 H4A 108.7 . . ? C5 C4 H4A 108.7 . . ? C3 C4 H4B 108.7 . . ? C5 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? C6 C5 C4 114.3(2) . . ? C6 C5 H5A 108.7 . . ? C4 C5 H5A 108.7 . . ? C6 C5 H5B 108.7 . . ? C4 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? C5 C6 C7 114.8(2) . . ? C5 C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? C5 C6 H6B 108.6 . . ? C7 C6 H6B 108.6 . . ? H6A C6 H6B 107.5 . . ? C8 C7 C6 115.5(2) . . ? C8 C7 H7A 108.4 . . ? C6 C7 H7A 108.4 . . ? C8 C7 H7B 108.4 . . ? C6 C7 H7B 108.4 . . ? H7A C7 H7B 107.5 . . ? C9 C8 C7 114.6(2) . . ? C9 C8 H8A 108.6 . . ? C7 C8 H8A 108.6 . . ? C9 C8 H8B 108.6 . . ? C7 C8 H8B 108.6 . . ? H8A C8 H8B 107.6 . . ? C10 C9 C8 115.5(2) . . ? C10 C9 H9A 108.4 . . ? C8 C9 H9A 108.4 . . ? C10 C9 H9B 108.4 . . ? C8 C9 H9B 108.4 . . ? H9A C9 H9B 107.5 . . ? C9 C10 C11 113.9(2) . . ? C9 C10 H10A 108.8 . . ? C11 C10 H10A 108.8 . . ? C9 C10 H10B 108.8 . . ? C11 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C10 C11 C12 114.3(2) . . ? C10 C11 H11A 108.7 . . ? C12 C11 H11A 108.7 . . ? C10 C11 H11B 108.7 . . ? C12 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C1 C12 C11 115.4(2) . . ? C1 C12 H12A 108.4 . . ? C11 C12 H12A 108.4 . . ? C1 C12 H12B 108.4 . . ? C11 C12 H12B 108.4 . . ? H12A C12 H12B 107.5 . . ? O2 C13 C14 111.74(17) . . ? O2 C13 C2 106.74(17) . . ? C14 C13 C2 112.11(17) . . ? O2 C13 H13 108.7 . . ? C14 C13 H13 108.7 . . ? C2 C13 H13 108.7 . . ? C15 C14 C19 117.6(2) . . ? C15 C14 C13 121.5(2) . . ? C19 C14 C13 120.92(19) . . ? C14 C15 C16 120.7(2) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C17 C16 C15 121.7(2) . . ? C17 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C16 C17 C18 117.2(2) . . ? C16 C17 C20 122.4(3) . . ? C18 C17 C20 120.4(3) . . ? C17 C18 C19 121.9(2) . . ? C17 C18 H18 119.0 . . ? C19 C18 H18 119.0 . . ? C14 C19 C18 120.9(2) . . ? C14 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C21 C20 C17 114.1(2) . . ? C21 C20 H20A 108.7 . . ? C17 C20 H20A 108.7 . . ? C21 C20 H20B 108.7 . . ? C17 C20 H20B 108.7 . . ? H20A C20 H20B 107.6 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C13 O2 H2O 108(3) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -118.9(2) . . . . ? C12 C1 C2 C3 64.6(2) . . . . ? O1 C1 C2 C13 114.6(2) . . . . ? C12 C1 C2 C13 -61.9(3) . . . . ? C1 C2 C3 C4 64.0(3) . . . . ? C13 C2 C3 C4 -170.90(18) . . . . ? C2 C3 C4 C5 -167.0(2) . . . . ? C3 C4 C5 C6 75.0(3) . . . . ? C4 C5 C6 C7 71.7(3) . . . . ? C5 C6 C7 C8 -152.4(3) . . . . ? C6 C7 C8 C9 64.8(3) . . . . ? C7 C8 C9 C10 64.2(3) . . . . ? C8 C9 C10 C11 -165.6(2) . . . . ? C9 C10 C11 C12 71.7(3) . . . . ? O1 C1 C12 C11 28.1(3) . . . . ? C2 C1 C12 C11 -155.5(2) . . . . ? C10 C11 C12 C1 71.8(3) . . . . ? C3 C2 C13 O2 -172.93(17) . . . . ? C1 C2 C13 O2 -46.8(2) . . . . ? C3 C2 C13 C14 64.4(2) . . . . ? C1 C2 C13 C14 -169.43(17) . . . . ? O2 C13 C14 C15 130.0(2) . . . . ? C2 C13 C14 C15 -110.2(2) . . . . ? O2 C13 C14 C19 -51.7(3) . . . . ? C2 C13 C14 C19 68.1(3) . . . . ? C19 C14 C15 C16 0.3(3) . . . . ? C13 C14 C15 C16 178.69(19) . . . . ? C14 C15 C16 C17 -0.5(4) . . . . ? C15 C16 C17 C18 0.8(4) . . . . ? C15 C16 C17 C20 178.5(2) . . . . ? C16 C17 C18 C19 -1.0(4) . . . . ? C20 C17 C18 C19 -178.8(2) . . . . ? C15 C14 C19 C18 -0.6(3) . . . . ? C13 C14 C19 C18 -178.9(2) . . . . ? C17 C18 C19 C14 0.9(4) . . . . ? C16 C17 C20 C21 -100.7(3) . . . . ? C18 C17 C20 C21 77.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.260 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.046 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2O O1 0.91(5) 2.04(5) 2.921(4) 164(4) 2_655 C12 H12A O2 0.97 2.50 3.475(5) 178 2_655 # [ 2655. ] = 1-x,1/2+y,1/2-z # 6-Membered Ring ( 1) C(14) C(15) C(16) C(17) C(18) C(19) # Attachment '- 5c_deposit_bks-vit-msc14_revised.cif' data_5c _database_code_depnum_ccdc_archive 'CCDC 843592' #TrackingRef '- 5c_deposit_bks-vit-msc14_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-(2,4-dichlorobenzylidene)cyclododecanone ; _chemical_name_common 2-(2,4-dichlorobenzylidene)cyclododecanone _chemical_melting_point ? _chemical_formula_moiety 'C19 H24 Cl2 O' _chemical_formula_sum 'C19 H24 Cl2 O' _chemical_formula_weight 339.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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' _cell_length_a 8.0433(6) _cell_length_b 9.0769(10) _cell_length_c 12.4273(10) _cell_angle_alpha 103.780(8) _cell_angle_beta 92.678(6) _cell_angle_gamma 92.933(7) _cell_volume 878.40(14) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 6274 _cell_measurement_theta_min 2.9591 _cell_measurement_theta_max 29.1506 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.369 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.83210 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details '(CrysAlis Pro; Oxford Diffraction, 2010)' _exptl_special_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur Eos Gemini' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 15.9821 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 10548 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3443 _reflns_number_gt 2867 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0436P)^2^+0.2428P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.026(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3443 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0949 _refine_ls_wR_factor_gt 0.0889 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1970(2) 0.92899(19) 0.36984(12) 0.0407(4) Uani 1 1 d . . . C2 C 0.34810(19) 0.83660(17) 0.35904(12) 0.0352(3) Uani 1 1 d . . . C3 C 0.5012(2) 0.90967(19) 0.32330(14) 0.0434(4) Uani 1 1 d . . . H3A H 0.5970 0.8535 0.3351 0.052 Uiso 1 1 calc R . . H3B H 0.5210 1.0126 0.3686 0.052 Uiso 1 1 calc R . . C4 C 0.4831(2) 0.91365(19) 0.20091(15) 0.0450(4) Uani 1 1 d . . . H4A H 0.3844 0.9663 0.1891 0.054 Uiso 1 1 calc R . . H4B H 0.5787 0.9716 0.1838 0.054 Uiso 1 1 calc R . . C5 C 0.4695(2) 0.7579(2) 0.12159(15) 0.0485(4) Uani 1 1 d . . . H5A H 0.3839 0.6954 0.1453 0.058 Uiso 1 1 calc R . . H5B H 0.5744 0.7110 0.1263 0.058 Uiso 1 1 calc R . . C6 C 0.4279(3) 0.7588(3) 0.00060(16) 0.0598(5) Uani 1 1 d . . . H6A H 0.5090 0.8268 -0.0217 0.072 Uiso 1 1 calc R . . H6B H 0.4383 0.6574 -0.0453 0.072 Uiso 1 1 calc R . . C7 C 0.2541(3) 0.8077(3) -0.02126(16) 0.0602(5) Uani 1 1 d . . . H7A H 0.2449 0.8224 -0.0961 0.072 Uiso 1 1 calc R . . H7B H 0.2403 0.9049 0.0296 0.072 Uiso 1 1 calc R . . C8 C 0.1122(3) 0.6949(2) -0.00857(16) 0.0616(5) Uani 1 1 d . . . H8A H 0.0853 0.6244 -0.0800 0.074 Uiso 1 1 calc R . . H8B H 0.1512 0.6366 0.0426 0.074 Uiso 1 1 calc R . . C9 C -0.0456(2) 0.7680(2) 0.03303(16) 0.0601(5) Uani 1 1 d . . . H9A H -0.1347 0.6892 0.0246 0.072 Uiso 1 1 calc R . . H9B H -0.0776 0.8357 -0.0131 0.072 Uiso 1 1 calc R . . C10 C -0.0288(2) 0.8575(2) 0.15358(15) 0.0504(4) Uani 1 1 d . . . H10A H -0.1235 0.9198 0.1683 0.060 Uiso 1 1 calc R . . H10B H 0.0710 0.9254 0.1645 0.060 Uiso 1 1 calc R . . C11 C -0.0192(2) 0.7599(2) 0.23729(15) 0.0470(4) Uani 1 1 d . . . H11A H 0.0644 0.6867 0.2162 0.056 Uiso 1 1 calc R . . H11B H -0.1257 0.7036 0.2348 0.056 Uiso 1 1 calc R . . C12 C 0.0242(2) 0.8521(2) 0.35617(14) 0.0467(4) Uani 1 1 d . . . H12A H -0.0563 0.9285 0.3764 0.056 Uiso 1 1 calc R . . H12B H 0.0163 0.7851 0.4063 0.056 Uiso 1 1 calc R . . C13 C 0.33733(19) 0.69686(17) 0.37647(12) 0.0354(3) Uani 1 1 d . . . H13 H 0.2334 0.6620 0.3934 0.043 Uiso 1 1 calc R . . C14 C 0.47170(19) 0.59220(17) 0.37183(12) 0.0329(3) Uani 1 1 d . . . C15 C 0.44986(19) 0.44351(17) 0.30820(12) 0.0346(3) Uani 1 1 d . . . C16 C 0.5720(2) 0.34083(18) 0.30208(12) 0.0394(4) Uani 1 1 d . . . H16 H 0.5538 0.2422 0.2584 0.047 Uiso 1 1 calc R . . C17 C 0.7214(2) 0.38798(19) 0.36233(13) 0.0389(4) Uani 1 1 d . . . C18 C 0.7482(2) 0.53303(19) 0.42860(13) 0.0413(4) Uani 1 1 d . . . H18 H 0.8489 0.5632 0.4698 0.050 Uiso 1 1 calc R . . C19 C 0.6237(2) 0.63295(18) 0.43293(13) 0.0385(4) Uani 1 1 d . . . H19 H 0.6418 0.7307 0.4781 0.046 Uiso 1 1 calc R . . Cl1 Cl 0.26222(6) 0.38208(6) 0.23205(4) 0.06100(17) Uani 1 1 d . . . Cl2 Cl 0.87742(6) 0.26072(6) 0.35561(4) 0.05906(17) Uani 1 1 d . . . O1 O 0.21587(18) 1.06629(14) 0.38612(12) 0.0631(4) Uani 1 1 d . . . 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 0.0491(10) 0.0405(9) 0.0298(8) 0.0021(6) -0.0001(7) 0.0088(7) C2 0.0382(8) 0.0354(8) 0.0297(7) 0.0040(6) -0.0019(6) 0.0037(6) C3 0.0384(9) 0.0373(9) 0.0540(10) 0.0127(7) -0.0053(7) -0.0024(7) C4 0.0401(9) 0.0434(10) 0.0566(10) 0.0219(8) 0.0072(7) 0.0008(7) C5 0.0469(10) 0.0510(10) 0.0515(10) 0.0170(8) 0.0101(8) 0.0104(8) C6 0.0652(13) 0.0708(13) 0.0480(11) 0.0183(9) 0.0213(9) 0.0121(10) C7 0.0692(13) 0.0746(14) 0.0420(10) 0.0221(9) 0.0077(9) 0.0127(11) C8 0.0674(13) 0.0625(12) 0.0463(11) -0.0024(9) -0.0034(9) 0.0043(10) C9 0.0538(11) 0.0695(13) 0.0530(11) 0.0099(9) -0.0135(9) 0.0045(10) C10 0.0431(10) 0.0547(11) 0.0531(10) 0.0118(8) -0.0021(8) 0.0113(8) C11 0.0336(9) 0.0509(10) 0.0551(10) 0.0106(8) -0.0008(7) 0.0014(7) C12 0.0403(9) 0.0564(11) 0.0466(10) 0.0144(8) 0.0114(7) 0.0145(8) C13 0.0354(8) 0.0404(9) 0.0304(7) 0.0085(6) 0.0025(6) 0.0017(6) C14 0.0367(8) 0.0338(8) 0.0298(7) 0.0112(6) 0.0027(6) 0.0004(6) C15 0.0337(8) 0.0384(8) 0.0305(7) 0.0074(6) -0.0003(6) -0.0026(6) C16 0.0471(9) 0.0349(8) 0.0338(8) 0.0035(6) 0.0031(7) 0.0032(7) C17 0.0394(9) 0.0455(9) 0.0363(8) 0.0165(7) 0.0070(6) 0.0099(7) C18 0.0382(9) 0.0464(9) 0.0404(9) 0.0154(7) -0.0076(7) -0.0016(7) C19 0.0460(9) 0.0332(8) 0.0349(8) 0.0081(6) -0.0057(7) -0.0030(7) Cl1 0.0437(3) 0.0569(3) 0.0711(3) -0.0011(2) -0.0183(2) -0.0041(2) Cl2 0.0538(3) 0.0658(3) 0.0604(3) 0.0157(2) 0.0053(2) 0.0263(2) O1 0.0659(9) 0.0384(7) 0.0760(9) -0.0037(6) -0.0091(7) 0.0128(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.214(2) . ? C1 C2 1.504(2) . ? C1 C12 1.507(2) . ? C2 C13 1.336(2) . ? C2 C3 1.504(2) . ? C3 C4 1.530(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.514(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.527(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.520(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.533(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.518(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.521(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.521(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.529(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.469(2) . ? C13 H13 0.9300 . ? C14 C15 1.390(2) . ? C14 C19 1.393(2) . ? C15 C16 1.381(2) . ? C15 Cl1 1.7359(15) . ? C16 C17 1.378(2) . ? C16 H16 0.9300 . ? C17 C18 1.377(2) . ? C17 Cl2 1.7404(16) . ? C18 C19 1.380(2) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 119.13(16) . . ? O1 C1 C12 120.28(15) . . ? C2 C1 C12 120.55(14) . . ? C13 C2 C1 119.65(14) . . ? C13 C2 C3 124.70(14) . . ? C1 C2 C3 115.58(13) . . ? C2 C3 C4 111.70(13) . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 107.9 . . ? C5 C4 C3 113.82(14) . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4B 108.8 . . ? C3 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C4 C5 C6 114.43(15) . . ? C4 C5 H5A 108.7 . . ? C6 C5 H5A 108.7 . . ? C4 C5 H5B 108.7 . . ? C6 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? C7 C6 C5 114.03(15) . . ? C7 C6 H6A 108.7 . . ? C5 C6 H6A 108.7 . . ? C7 C6 H6B 108.7 . . ? C5 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C6 C7 C8 114.42(17) . . ? C6 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? C6 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C9 C8 C7 114.41(18) . . ? C9 C8 H8A 108.7 . . ? C7 C8 H8A 108.7 . . ? C9 C8 H8B 108.7 . . ? C7 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? C8 C9 C10 113.99(15) . . ? C8 C9 H9A 108.8 . . ? C10 C9 H9A 108.8 . . ? C8 C9 H9B 108.8 . . ? C10 C9 H9B 108.8 . . ? H9A C9 H9B 107.6 . . ? C9 C10 C11 114.39(16) . . ? C9 C10 H10A 108.7 . . ? C11 C10 H10A 108.7 . . ? C9 C10 H10B 108.7 . . ? C11 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C10 C11 C12 113.23(15) . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C1 C12 C11 112.19(13) . . ? C1 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? C1 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C2 C13 C14 127.15(14) . . ? C2 C13 H13 116.4 . . ? C14 C13 H13 116.4 . . ? C15 C14 C19 116.42(14) . . ? C15 C14 C13 120.81(13) . . ? C19 C14 C13 122.73(14) . . ? C16 C15 C14 122.84(14) . . ? C16 C15 Cl1 117.77(12) . . ? C14 C15 Cl1 119.39(12) . . ? C15 C16 C17 118.38(14) . . ? C15 C16 H16 120.8 . . ? C17 C16 H16 120.8 . . ? C18 C17 C16 121.14(15) . . ? C18 C17 Cl2 119.64(13) . . ? C16 C17 Cl2 119.21(13) . . ? C17 C18 C19 119.06(15) . . ? C17 C18 H18 120.5 . . ? C19 C18 H18 120.5 . . ? C18 C19 C14 122.13(15) . . ? C18 C19 H19 118.9 . . ? C14 C19 H19 118.9 . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C13 158.76(16) . . . . ? C12 C1 C2 C13 -23.6(2) . . . . ? O1 C1 C2 C3 -24.0(2) . . . . ? C12 C1 C2 C3 153.62(14) . . . . ? C13 C2 C3 C4 105.13(17) . . . . ? C1 C2 C3 C4 -71.98(17) . . . . ? C2 C3 C4 C5 -64.90(19) . . . . ? C3 C4 C5 C6 172.15(15) . . . . ? C4 C5 C6 C7 -67.0(2) . . . . ? C5 C6 C7 C8 -68.3(2) . . . . ? C6 C7 C8 C9 147.71(17) . . . . ? C7 C8 C9 C10 -69.7(2) . . . . ? C8 C9 C10 C11 -72.1(2) . . . . ? C9 C10 C11 C12 171.21(15) . . . . ? O1 C1 C12 C11 110.48(18) . . . . ? C2 C1 C12 C11 -67.08(19) . . . . ? C10 C11 C12 C1 -65.10(19) . . . . ? C1 C2 C13 C14 -178.69(13) . . . . ? C3 C2 C13 C14 4.3(2) . . . . ? C2 C13 C14 C15 -128.62(17) . . . . ? C2 C13 C14 C19 53.8(2) . . . . ? C19 C14 C15 C16 -1.7(2) . . . . ? C13 C14 C15 C16 -179.43(14) . . . . ? C19 C14 C15 Cl1 178.51(11) . . . . ? C13 C14 C15 Cl1 0.83(19) . . . . ? C14 C15 C16 C17 0.4(2) . . . . ? Cl1 C15 C16 C17 -179.84(11) . . . . ? C15 C16 C17 C18 1.0(2) . . . . ? C15 C16 C17 Cl2 -179.81(11) . . . . ? C16 C17 C18 C19 -1.0(2) . . . . ? Cl2 C17 C18 C19 179.81(12) . . . . ? C17 C18 C19 C14 -0.4(2) . . . . ? C15 C14 C19 C18 1.7(2) . . . . ? C13 C14 C19 C18 179.37(14) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.207 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.035 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C19 H19 O1 0.93 2.38 3.259(2) 157 2_676 # [ 2676. ] = 1-x,2-y,1-z #Cg(1) [ 1] -> Cg(1) [ 2666.01] 3.6776(10) 0 3.4309(6) 1.324 #[ 2666] = 1-X,1-Y,1-Z #6-Membered Ring ( 1) C(14) C(15) C(16) C(17) C(18) C(19)