#------------------------------------------------------------------------------ #$Date: 2014-08-21 06:03:27 +0300 (Thu, 21 Aug 2014) $ #$Revision: 122296 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/21/77/7217795.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7217795 loop_ _publ_author_name 'Feng, Xiao-lin' 'Yu, Yang' 'Gao, Hao' 'Mu, Zhen-qiang' 'Cheng, Xiao-rui' 'Zhou, Wen-xia' 'Yao, Xin-sheng' _publ_section_title ; New sesquiterpenoids from the rhizomes of Acorus tatarinowii ; _journal_name_full 'RSC Advances' _journal_paper_doi 10.1039/C4RA06481J _journal_year 2014 _chemical_absolute_configuration ad _chemical_formula_moiety 'C15 H22 O2' _chemical_formula_sum 'C15 H22 O2' _chemical_formula_weight 234.33 _chemical_name_common acoronene _chemical_name_systematic ; ? ; _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2014-08-15 _audit_creation_method ; Olex2 1.2 (compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4862) ; _cell_angle_alpha 90.00 _cell_angle_beta 108.159(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 8.5501(2) _cell_length_b 6.48130(10) _cell_length_c 12.5837(3) _cell_measurement_reflns_used 6687 _cell_measurement_temperature 173.01(18) _cell_measurement_theta_max 62.5766 _cell_measurement_theta_min 3.6936 _cell_volume 662.60(3) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 173.01(18) _diffrn_detector_area_resol_mean 16.0288 _diffrn_measured_fraction_theta_full 0.978 _diffrn_measured_fraction_theta_max 0.978 _diffrn_measurement_details ; 1 omega -101.00 -60.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -32.8684 -178.0000 -90.0000 41 2 omega 55.00 81.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 32.8684 57.0000 0.0000 26 3 omega 14.00 101.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 32.8684 57.0000 -150.0000 87 4 omega -16.00 99.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 32.8684 0.0000 -180.0000 115 5 omega -37.00 58.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 32.8684 -38.0000 150.0000 95 6 omega 20.00 82.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 -94.0000 30.0000 62 7 omega 87.00 159.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 45.0000 60.0000 72 8 omega 34.00 73.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 -94.0000 90.0000 39 9 omega 39.00 82.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 -94.0000 150.0000 43 10 omega 21.00 47.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 -30.0000 90.0000 26 11 omega 82.00 161.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 83.0000 -102.0000 79 12 omega 18.00 65.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 -30.0000 -90.0000 47 13 omega 106.00 132.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 77.0000 -180.0000 26 14 omega 18.00 62.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 -30.0000 120.0000 44 15 omega 71.00 99.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 77.0000 -180.0000 28 16 omega 39.00 78.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 -111.0000 -120.0000 39 17 omega 75.00 101.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 77.0000 0.0000 26 18 omega 128.00 157.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 77.0000 0.0000 29 19 omega 39.00 70.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 -45.0000 120.0000 31 20 omega 26.00 72.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 -77.0000 -120.0000 46 21 omega 60.00 126.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 77.0000 -150.0000 66 22 omega 54.00 148.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 15.0000 30.0000 94 23 omega -109.00 -53.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -32.8684 178.0000 -150.0000 56 24 omega -109.00 -53.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -32.8684 178.0000 0.0000 56 25 omega -46.00 0.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -32.8684 -83.0000 102.0000 46 26 omega 35.00 109.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 32.8684 178.0000 -180.0000 74 27 omega 10.00 104.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 32.8684 46.0000 -49.0000 94 28 omega 3.00 103.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 32.8684 77.0000 30.0000 100 29 omega -134.00 -34.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -64.0000 -77.0000 30.0000 100 30 omega -134.00 -34.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -64.0000 -77.0000 90.0000 100 31 omega -134.00 -34.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -64.0000 -77.0000 -30.0000 100 32 omega -134.00 -34.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -64.0000 -77.0000 -90.0000 100 33 omega 61.00 163.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 30.0000 150.0000 102 34 omega 60.00 161.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 77.0000 150.0000 101 35 omega 18.00 90.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 -111.0000 120.0000 72 36 omega 60.00 161.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 77.0000 60.0000 101 37 omega 60.00 161.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 77.0000 -30.0000 101 38 omega 61.00 163.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 30.0000 -60.0000 102 39 omega 19.00 83.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 -94.0000 -60.0000 64 40 omega 18.00 69.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 90.5000 -30.0000 0.0000 51 41 omega -109.00 -57.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -32.8684 -178.0000 90.0000 52 42 omega -102.00 -11.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -32.8684 -57.0000 150.0000 91 43 omega 3.00 103.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 32.8684 77.0000 -90.0000 100 ; _diffrn_measurement_device_type 'Gemini S ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0984334000 _diffrn_orient_matrix_UB_12 -0.1991129000 _diffrn_orient_matrix_UB_13 -0.0416509000 _diffrn_orient_matrix_UB_21 0.1242104000 _diffrn_orient_matrix_UB_22 -0.0622737000 _diffrn_orient_matrix_UB_23 -0.0605328000 _diffrn_orient_matrix_UB_31 0.1042260000 _diffrn_orient_matrix_UB_32 -0.1138156000 _diffrn_orient_matrix_UB_33 0.1057984000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0154 _diffrn_reflns_av_unetI/netI 0.0109 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 8159 _diffrn_reflns_theta_full 62.66 _diffrn_reflns_theta_max 62.66 _diffrn_reflns_theta_min 3.70 _diffrn_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_source_current n/a _diffrn_source_voltage n/a _exptl_absorpt_coefficient_mu 0.595 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.58812 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.174 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.152 _refine_diff_density_min -0.118 _refine_diff_density_rms 0.023 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(18) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 158 _refine_ls_number_reflns 2074 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.074 _refine_ls_R_factor_all 0.0256 _refine_ls_R_factor_gt 0.0254 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0313P)^2^+0.1213P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0629 _refine_ls_wR_factor_ref 0.0630 _reflns_number_gt 2064 _reflns_number_total 2074 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c4ra06481j2.cif _[local]_cod_data_source_block acoronene _cod_original_cell_volume 662.60(2) _cod_database_code 7217795 _reflns_odcompleteness_completeness 98.14 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 61.08 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C1(H1), C4(H4), C11(H11) 2.b Secondary CH2 refined with riding coordinates: C6(H6A,H6B), C10(H10A,H10B), C3(H3A,H3B) 2.c Aromatic/amide H refined with riding coordinates: C9(H9) 2.d Idealised Me refined as rotating group: C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C12(H12A,H12B, H12C) ; _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z' 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_calc_flag _atom_site_refinement_flags_posn O1 O 0.96305(11) 0.48730(16) 0.00126(7) 0.0316(2) Uani 1 d . O2 O 1.24013(13) 0.78987(16) -0.45150(8) 0.0345(2) Uani 1 d . C1 C 0.95716(15) 0.57203(18) -0.18843(10) 0.0218(3) Uani 1 d . H1 H 0.9520 0.7227 -0.1841 0.026 Uiso 1 calc R C7 C 1.19249(15) 0.6453(2) -0.40706(10) 0.0236(3) Uani 1 d . C6 C 1.07027(16) 0.6775(2) -0.34394(11) 0.0239(3) Uani 1 d . H6A H 0.9599 0.6630 -0.3958 0.029 Uiso 1 calc R H6B H 1.0814 0.8176 -0.3154 0.029 Uiso 1 calc R C5 C 1.09014(14) 0.52826(19) -0.24610(10) 0.0205(3) Uani 1 d . C2 C 1.03314(15) 0.5008(2) -0.06842(10) 0.0236(3) Uani 1 d . C10 C 1.08118(16) 0.3089(2) -0.29426(11) 0.0243(3) Uani 1 d . H10A H 1.1121 0.2106 -0.2331 0.029 Uiso 1 calc R H10B H 0.9685 0.2796 -0.3387 0.029 Uiso 1 calc R C9 C 1.19130(16) 0.2803(2) -0.36551(10) 0.0266(3) Uani 1 d . H9 H 1.2249 0.1466 -0.3742 0.032 Uiso 1 calc R C8 C 1.24501(16) 0.4315(2) -0.41749(10) 0.0247(3) Uani 1 d . C4 C 1.25510(15) 0.5521(2) -0.14801(10) 0.0240(3) Uani 1 d . H4 H 1.3415 0.4711 -0.1645 0.029 Uiso 1 calc R C11 C 0.77831(14) 0.5031(2) -0.24845(10) 0.0248(3) Uani 1 d . H11 H 0.7621 0.5064 -0.3290 0.030 Uiso 1 calc R C14 C 1.35224(19) 0.3957(2) -0.49008(12) 0.0340(3) Uani 1 d . H14A H 1.2973 0.4453 -0.5642 0.051 Uiso 1 calc GR H14B H 1.3736 0.2507 -0.4929 0.051 Uiso 1 calc GR H14C H 1.4544 0.4681 -0.4596 0.051 Uiso 1 calc GR C13 C 0.73823(18) 0.2846(3) -0.21938(12) 0.0367(3) Uani 1 d . H13A H 0.8217 0.1913 -0.2263 0.055 Uiso 1 calc GR H13B H 0.6334 0.2434 -0.2696 0.055 Uiso 1 calc GR H13C H 0.7344 0.2818 -0.1440 0.055 Uiso 1 calc GR C15 C 1.31330(17) 0.7749(2) -0.12228(12) 0.0328(3) Uani 1 d . H15A H 1.3376 0.8327 -0.1856 0.049 Uiso 1 calc GR H15B H 1.4106 0.7774 -0.0584 0.049 Uiso 1 calc GR H15C H 1.2283 0.8544 -0.1067 0.049 Uiso 1 calc GR C3 C 1.21358(16) 0.4552(2) -0.04902(11) 0.0282(3) Uani 1 d . H3A H 1.2328 0.3075 -0.0465 0.034 Uiso 1 calc R H3B H 1.2806 0.5155 0.0209 0.034 Uiso 1 calc R C12 C 0.65597(16) 0.6546(3) -0.22539(12) 0.0335(3) Uani 1 d . H12A H 0.6686 0.6550 -0.1469 0.050 Uiso 1 calc GR H12B H 0.5459 0.6135 -0.2666 0.050 Uiso 1 calc GR H12C H 0.6765 0.7906 -0.2482 0.050 Uiso 1 calc GR loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0356(5) 0.0376(6) 0.0260(5) 0.0020(4) 0.0157(4) -0.0028(4) O2 0.0442(6) 0.0311(5) 0.0366(5) 0.0046(5) 0.0246(5) -0.0012(5) C1 0.0212(6) 0.0214(6) 0.0242(6) 0.0006(5) 0.0092(5) -0.0007(5) C7 0.0236(6) 0.0286(7) 0.0183(6) 0.0004(6) 0.0063(5) -0.0004(6) C6 0.0255(7) 0.0233(6) 0.0249(7) 0.0028(5) 0.0106(5) 0.0032(5) C5 0.0218(6) 0.0211(6) 0.0194(6) -0.0003(5) 0.0076(5) 0.0002(5) C2 0.0282(7) 0.0207(6) 0.0235(6) -0.0017(5) 0.0104(5) -0.0032(5) C10 0.0262(6) 0.0225(7) 0.0244(7) 0.0002(5) 0.0081(5) -0.0006(5) C9 0.0301(7) 0.0234(7) 0.0252(7) -0.0064(6) 0.0071(5) 0.0020(6) C8 0.0250(7) 0.0281(7) 0.0208(6) -0.0048(5) 0.0069(5) -0.0017(5) C4 0.0210(6) 0.0286(7) 0.0233(6) -0.0030(6) 0.0083(5) 0.0026(5) C11 0.0227(6) 0.0315(7) 0.0210(6) 0.0004(6) 0.0079(5) -0.0028(6) C14 0.0347(8) 0.0384(8) 0.0329(8) -0.0085(6) 0.0162(6) -0.0013(7) C13 0.0315(7) 0.0388(8) 0.0395(8) 0.0003(7) 0.0108(6) -0.0112(7) C15 0.0276(7) 0.0376(8) 0.0357(7) -0.0108(7) 0.0134(6) -0.0068(6) C3 0.0277(7) 0.0336(8) 0.0210(6) -0.0004(6) 0.0041(5) 0.0013(6) C12 0.0231(7) 0.0448(9) 0.0338(8) -0.0048(7) 0.0105(6) -0.0010(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 C1 C5 105.10(10) C2 C1 C11 116.72(10) C11 C1 C5 118.40(10) O2 C7 C6 121.14(12) O2 C7 C8 121.64(11) C8 C7 C6 117.15(11) C7 C6 C5 114.40(10) C1 C5 C4 102.96(9) C6 C5 C1 110.23(10) C6 C5 C10 106.71(10) C6 C5 C4 114.71(10) C10 C5 C1 113.51(10) C10 C5 C4 108.89(10) O1 C2 C1 126.02(11) O1 C2 C3 125.40(11) C3 C2 C1 108.56(10) C9 C10 C5 112.70(11) C8 C9 C10 125.27(13) C7 C8 C14 117.41(11) C9 C8 C7 118.99(11) C9 C8 C14 123.56(12) C15 C4 C5 114.45(11) C15 C4 C3 110.94(11) C3 C4 C5 102.74(10) C13 C11 C1 114.37(11) C12 C11 C1 110.68(11) C12 C11 C13 109.42(11) C2 C3 C4 105.76(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C2 1.2095(15) O2 C7 1.2243(16) C1 C5 1.5538(16) C1 C2 1.5180(17) C1 C11 1.5455(17) C7 C6 1.5112(17) C7 C8 1.4748(18) C6 C5 1.5331(17) C5 C10 1.5382(17) C5 C4 1.5657(16) C2 C3 1.5140(18) C10 C9 1.5002(17) C9 C8 1.336(2) C8 C14 1.5003(19) C4 C15 1.5286(19) C4 C3 1.5321(18) C11 C13 1.528(2) C11 C12 1.5271(19)