#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/73/2007310.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2007310 loop_ _publ_author_name 'Rivera, Patricio' 'Manr\'iquez, Victor' 'Wittke, Oscar' _publ_section_title ; Absolute Configuration of a Tetrachloro Monoterpene from Plocamium cartilagineum ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 816 _journal_page_last 818 _journal_paper_doi 10.1107/S0108270197017976 _journal_volume 54 _journal_year 1998 _chemical_formula_sum 'C10 H14 Cl4' _chemical_formula_weight 276.01 _chemical_name_systematic ; (1R*,2R*,4R*,5S*,1'E)-1,2,4-trichloro-5-(2'-chloroethenyl-1,5- dimethylcyclohexane) ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 103.76(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 7.2690(10) _cell_length_b 8.030(2) _cell_length_c 11.055(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 12.5 _cell_measurement_theta_min 7.5 _cell_volume 626.8(2) _computing_cell_refinement P3/P4-PC _computing_data_collection 'P3/P4-PC Siemens (1991)' _computing_data_reduction 'XDISK (SHELXTL; Sheldrick, 1994)' _computing_molecular_graphics 'XP (SHELXTL)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _diffrn_ambient_temperature 295 _diffrn_measurement_device 'Siemens R3m' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0102 _diffrn_reflns_av_sigmaI/netI 0.0099 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 2534 _diffrn_reflns_theta_max 27.56 _diffrn_reflns_theta_min 1.90 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 47 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.905 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_meas ? _exptl_crystal_description prism _exptl_crystal_F_000 284 _exptl_crystal_size_max 0.92 _exptl_crystal_size_mid 0.64 _exptl_crystal_size_min 0.60 _refine_diff_density_max 0.183 _refine_diff_density_min -0.173 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack 0.00(7) _refine_ls_extinction_coef 0.006(3) _refine_ls_extinction_method 'SHELXL93 (Sheldrick, 1993)' _refine_ls_goodness_of_fit_all 1.090 _refine_ls_goodness_of_fit_obs 1.091 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 128 _refine_ls_number_reflns 2158 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.091 _refine_ls_restrained_S_obs 1.090 _refine_ls_R_factor_all 0.0266 _refine_ls_R_factor_obs .0258 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0466P)^2^+0.0833P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0724 _refine_ls_wR_factor_obs .0713 _reflns_number_observed 2100 _reflns_number_total '2159 (including Friedel pairs)' _reflns_observed_criterion >2sigma(I) _cod_data_source_file bs1027.cif _cod_data_source_block natur _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'Not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0466P)^2^+0.0833P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0466P)^2^+0.0833P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 2007310 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 .0733(6) .0866(4) .0384(2) .0119(4) -.0008(2) .0003(3) Cl2 .0737(6) .0725(4) .0559(3) -.0100(4) .0291(3) .0064(3) Cl3 .0527(5) .0630(3) .0500(3) -.0014(3) -.0003(2) .0169(2) Cl4 .0653(5) .0862(4) .0523(3) .0084(4) .0241(3) .0050(3) C1' .053(2) .0380(9) .0574(11) -.0007(9) .0201(10) .0028(8) C2' .050(2) .0523(11) .0485(10) .0028(11) .0156(10) .0018(9) C1 .064(2) .0385(9) .0383(9) .0090(10) .0108(9) .0014(7) C2 .051(2) .0443(9) .0394(9) -.0059(10) .0132(9) .0022(7) C3 .045(2) .0429(10) .0553(10) .0061(10) .0167(9) -.0017(8) C4 .042(2) .0311(8) .0529(10) .0055(9) .0115(9) .0009(7) C5 .042(2) .0341(8) .0451(9) .0002(9) .0111(8) -.0025(7) C6 .044(2) .0359(8) .0433(9) .0084(9) .0097(8) -.0002(7) C7 .104(3) .0408(11) .0653(14) .0120(13) .0291(15) .0130(10) C8 .046(2) .0568(12) .0704(14) -.0118(12) .0164(11) -.0200(11) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol Cl1 -.26274(11) .00004(9) .51946(5) .0685(2) Uani d . 1 . Cl Cl2 .19659(11) .05985(9) .59372(6) .0650(2) Uani d . 1 . Cl Cl3 .12960(9) -.16254(8) .96962(5) .0573(2) Uani d . 1 . Cl Cl4 -.39803(11) -.14692(10) 1.13748(5) .0662(2) Uani d . 1 . Cl C1' -.2847(4) -.2056(2) .9288(2) .0482(6) Uani d . 1 . C H1'A -.2711(4) -.3171(2) .9610(2) .080 Uiso d R 1 . H C2' -.3500(4) -.0961(3) .9947(2) .0496(6) Uani d . 1 . C H2'A -.3731(4) .0155(3) .9635(2) .080 Uiso d R 1 . H C1 -.1381(4) .0696(3) .6736(2) .0470(6) Uani d . 1 . C C2 .0627(4) .0003(3) .7045(2) .0446(6) Uani d . 1 . C H2A .1265(4) .0467(3) .7833(2) .080 Uiso d R 1 . H C3 .0685(4) -.1877(2) .7194(2) .0470(5) Uani d . 1 . C H3A .0014(4) -.2388(2) .6431(2) .080 Uiso d R 1 . H H3B .1974(4) -.2256(2) .7371(2) .080 Uiso d R 1 . H C4 -.0220(3) -.2387(2) .8244(2) .0420(6) Uani d . 1 . C H4A -.0231(3) -.3582(2) .8278(2) .080 Uiso d R 1 . H C5 -.2258(3) -.1771(2) .8077(2) .0402(5) Uani d . 1 . C C6 -.2391(3) .0094(2) .7730(2) .0411(5) Uani d . 1 . C H6A -.1903(3) .0720(2) .8477(2) .080 Uiso d R 1 . H H6B -.3709(3) .0369(2) .7447(2) .080 Uiso d R 1 . H C7 -.1405(5) .2600(3) .6699(3) .0687(9) Uani d . 1 . C H7A -.0758(5) .3025(3) .7499(3) .080 Uiso d R 1 . H H7B -.0777(5) .2980(3) .6078(3) .080 Uiso d R 1 . H H7C -.2690(5) .2990(3) .6499(3) .080 Uiso d R 1 . H C8 -.3531(4) -.2878(3) .7081(2) .0573(6) Uani d . 1 . C H8A -.3386(4) -.4020(3) .7343(2) .080 Uiso d R 1 . H H8B -.4830(4) -.2551(3) .6974(2) .080 Uiso d R 1 . H H8C -.3167(4) -.2756(3) .6306(2) .080 Uiso d R 1 . H 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 3 2 4 1 9 1 3 0 10 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2' C1' C5 127.5(2) yes C1' C2' Cl4 121.8(2) yes C2 C1 C7 112.1(2) yes C2 C1 C6 108.7(2) yes C7 C1 C6 109.2(2) yes C2 C1 Cl1 109.57(15) yes C7 C1 Cl1 106.4(2) yes C6 C1 Cl1 110.9(2) yes C3 C2 C1 112.9(2) yes C3 C2 Cl2 109.4(2) yes C1 C2 Cl2 113.25(14) yes C2 C3 C4 110.2(2) yes C3 C4 C5 113.8(2) yes C3 C4 Cl3 107.5(2) yes C5 C4 Cl3 111.23(14) yes C1' C5 C4 108.2(2) yes C1' C5 C8 107.2(2) yes C4 C5 C8 107.4(2) yes C1' C5 C6 110.6(2) yes C4 C5 C6 110.2(2) yes C8 C5 C6 113.0(2) yes C1 C6 C5 118.1(2) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C1 . 1.817(2) yes Cl2 C2 . 1.800(2) yes Cl3 C4 . 1.823(2) yes Cl4 C2' . 1.745(2) yes C1' C2' . 1.302(3) yes C1' C5 . 1.516(3) yes C1 C2 . 1.523(4) yes C1 C7 . 1.529(3) yes C1 C6 . 1.537(3) yes C2 C3 . 1.518(3) yes C3 C4 . 1.520(3) yes C4 C5 . 1.531(4) yes C5 C8 . 1.541(3) yes C5 C6 . 1.543(3) yes 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 C5 C1' C2' Cl4 -176.1(2) C7 C1 C2 C3 175.1(2) C6 C1 C2 C3 54.3(2) Cl1 C1 C2 C3 -67.0(2) C7 C1 C2 Cl2 -59.9(2) C6 C1 C2 Cl2 179.32(14) Cl1 C1 C2 Cl2 58.0(2) C1 C2 C3 C4 -60.2(2) Cl2 C2 C3 C4 172.8(2) C2 C3 C4 C5 56.4(2) C2 C3 C4 Cl3 -67.2(2) C2' C1' C5 C4 125.0(3) C2' C1' C5 C8 -119.5(3) C2' C1' C5 C6 4.1(4) C3 C4 C5 C1' -168.8(2) Cl3 C4 C5 C1' -47.2(2) C3 C4 C5 C8 75.8(2) Cl3 C4 C5 C8 -162.6(2) C3 C4 C5 C6 -47.7(2) Cl3 C4 C5 C6 73.9(2) C2 C1 C6 C5 -47.8(2) C7 C1 C6 C5 -170.3(2) Cl1 C1 C6 C5 72.7(2) C1' C5 C6 C1 164.4(2) C4 C5 C6 C1 44.7(2) C8 C5 C6 C1 -75.4(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 10478348 2 PubChem 21775918