data_publication_text _publ_requested_journal J.Am.Chem.Soc. _publ_contact_author_name 'Robert M. Coates' _publ_contact_author_address ;Department of Chemistry University of Illinois 600 South Mathews Avenue, Urbana, IL 61801 (USA) ; _publ_contact_author_email coates@scs.uiuc.edu _publ_contact_author_fax (+1)217-244-8024 loop_ _publ_author_name _publ_author_address 'Coates, R. M.' ;Department of Chemistry University of Illinois 600 South Mathews Avenue, Urbana, IL 61801 (USA) ; 'Miles, R. B.' ;Department of Chemistry University of Illinois 600 South Mathews Avenue, Urbana, IL 61801 (USA) ; data_pub3face _audit_creation_method SHELXL-97 _audit_update_record ; 2005-03-21 text and data added, rbm ; _chemical_name_systematic (1S,3S,6R,9R)-3-Chloro-5,5,9-trimethylbicyclo[4.4.0]decan-1-ol _chemical_name_common (1S,3S,6R,9R)-3-Chloro-5,5,9-trimethylbicyclo[4.4.0]decan-1-ol _chemical_melting_point 318 _chemical_formula_moiety 'C13 H23 Cl O' _chemical_formula_sum 'C13 H23 Cl O' _chemical_formula_structural ? _chemical_formula_weight 230.76 _chemical_absolute_configuration rmad _chemical_formula_analytical ? _chemical_compound_source synthesis 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_int_tables_number 19 _symmetry_space_group_name_Hall 'P 2ac 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.702(3) _cell_length_b 9.187(4) _cell_length_c 24.444(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1280.5(10) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 876 _cell_measurement_theta_min 3.34 _cell_measurement_theta_max 24.41 _exptl_crystal_description platy _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.197 _exptl_crystal_density_method ? _exptl_crystal_F_000 504 _exptl_crystal_id pub3face _exptl_crystal_preparation ; The data crystal was mounted using oil (Parantone-N, Exxon) to a 0.4 mm cryo-loop (Hampton Research) with the (1 1 1) scattering planes roughly normal to the spindle axis. ; _exptl_absorpt_coefficient_mu 0.273 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.89026 _exptl_absorpt_correction_T_max 0.98644 _exptl_absorpt_process_details '(Bruker, 2001)' _exptl_special_details ; Four frame series were filtered for statistical outliers then corrected for absorption by integration using SHELXTL/XPREP (Bruker, 2001). A series of identical frames was collected twice during the experiment to monitor decay. No decay correction was applied. ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'normal-focus sealed tube' _diffrn_radiation_wavelength_id pub3face _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_device 'Siemens Platform/CCD' _diffrn_measurement_method 'profile data from \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 94 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 365 _diffrn_standards_decay_% 6.4 _diffrn_reflns_number 10050 _diffrn_reflns_av_R_equivalents 0.0920 _diffrn_reflns_av_sigmaI/netI 0.0692 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 25.33 _reflns_number_total 2325 _reflns_number_gt 1699 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.625 (Bruker, 2001)' _computing_cell_refinement 'SAINT V6.22 (Bruker, 2001)' _computing_data_reduction 'SAINT V6.22 (Bruker, 2001)' _computing_structure_solution 'SHELXTL V6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXTL V6.12 (Bruker, 2001)' _computing_molecular_graphics 'SHELXTL V6.12 (Bruker, 2001)' _computing_publication_material 'CIFTAB (Sheldrick, 2001)' _refine_special_details ; ? ; _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^)+(0.0214P)^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 noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0277(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(7) _refine_ls_number_reflns 2325 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0687 _refine_ls_wR_factor_gt 0.0640 _refine_ls_goodness_of_fit_ref 0.935 _refine_ls_restrained_S_all 0.935 _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 Cl1 Cl 0.52205(9) 0.74846(7) 0.23760(2) 0.05013(19) Uani 1 1 d . . . O1 O 0.5114(2) 0.55340(15) 0.34451(5) 0.0307(3) Uani 1 1 d . . . H1 H 0.4808 0.4826 0.3240 0.046 Uiso 1 1 calc R . . C1 C 0.7620(3) 0.5686(2) 0.34963(8) 0.0259(5) Uani 1 1 d . . . C2 C 0.8674(3) 0.4262(2) 0.37182(8) 0.0307(5) Uani 1 1 d . . . H2A H 0.8224 0.3458 0.3470 0.037 Uiso 1 1 calc R . . H2B H 1.0405 0.4344 0.3709 0.037 Uiso 1 1 calc R . . C3 C 0.7927(4) 0.3856(2) 0.43013(9) 0.0388(6) Uani 1 1 d . . . H3 H 0.8996 0.3059 0.4426 0.047 Uiso 1 1 calc R . . C4 C 0.8349(4) 0.5155(3) 0.46790(9) 0.0458(7) Uani 1 1 d . . . H4A H 1.0058 0.5317 0.4716 0.055 Uiso 1 1 calc R . . H4B H 0.7718 0.4929 0.5047 0.055 Uiso 1 1 calc R . . C5 C 0.7198(4) 0.6553(2) 0.44669(9) 0.0387(6) Uani 1 1 d . . . H5A H 0.5476 0.6421 0.4453 0.046 Uiso 1 1 calc R . . H5B H 0.7540 0.7364 0.4721 0.046 Uiso 1 1 calc R . . C6 C 0.8110(3) 0.6933(2) 0.38973(8) 0.0288(5) Uani 1 1 d . . . H6 H 0.9855 0.6972 0.3934 0.035 Uiso 1 1 calc R . . C7 C 0.7372(3) 0.8467(2) 0.36876(9) 0.0297(5) Uani 1 1 d . . . C8 C 0.8403(4) 0.8706(2) 0.31099(9) 0.0357(6) Uani 1 1 d . . . H8A H 0.7668 0.9590 0.2954 0.043 Uiso 1 1 calc R . . H8B H 1.0099 0.8911 0.3150 0.043 Uiso 1 1 calc R . . C9 C 0.8127(3) 0.7484(3) 0.26979(8) 0.0367(5) Uani 1 1 d . . . H9 H 0.9293 0.7669 0.2400 0.044 Uiso 1 1 calc R . . C10 C 0.8704(4) 0.6005(2) 0.29381(8) 0.0320(5) Uani 1 1 d . . . H10A H 1.0430 0.5923 0.2971 0.038 Uiso 1 1 calc R . . H10B H 0.8176 0.5247 0.2678 0.038 Uiso 1 1 calc R . . C11 C 0.5424(4) 0.3279(2) 0.43490(9) 0.0499(6) Uani 1 1 d . . . H11A H 0.4313 0.4073 0.4282 0.075 Uiso 1 1 calc R . . H11B H 0.5174 0.2888 0.4717 0.075 Uiso 1 1 calc R . . H11C H 0.5179 0.2506 0.4079 0.075 Uiso 1 1 calc R . . C12 C 0.8489(4) 0.9647(2) 0.40500(10) 0.0443(6) Uani 1 1 d . . . H12A H 0.8243 1.0605 0.3883 0.066 Uiso 1 1 calc R . . H12B H 1.0174 0.9461 0.4085 0.066 Uiso 1 1 calc R . . H12C H 0.7760 0.9628 0.4413 0.066 Uiso 1 1 calc R . . C13 C 0.4722(4) 0.8709(2) 0.36946(9) 0.0398(6) Uani 1 1 d . . . H13A H 0.4363 0.9667 0.3539 0.060 Uiso 1 1 calc R . . H13B H 0.4151 0.8666 0.4072 0.060 Uiso 1 1 calc R . . H13C H 0.3953 0.7951 0.3477 0.060 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 0.0607(4) 0.0466(3) 0.0431(3) 0.0111(3) -0.0199(3) -0.0010(4) O1 0.0266(8) 0.0310(8) 0.0346(9) -0.0028(6) -0.0032(7) 0.0001(7) C1 0.0232(11) 0.0315(12) 0.0229(12) -0.0006(10) -0.0006(9) 0.0026(10) C2 0.0333(11) 0.0318(12) 0.0270(12) -0.0025(10) -0.0034(10) 0.0058(10) C3 0.0506(15) 0.0402(15) 0.0255(13) 0.0064(11) -0.0040(11) 0.0097(11) C4 0.0603(16) 0.0533(17) 0.0238(14) 0.0023(11) -0.0007(11) 0.0089(13) C5 0.0479(13) 0.0411(13) 0.0271(13) -0.0096(11) 0.0039(10) -0.0001(11) C6 0.0212(11) 0.0369(14) 0.0283(12) -0.0055(10) -0.0012(8) 0.0026(9) C7 0.0254(11) 0.0283(12) 0.0353(13) -0.0029(10) -0.0017(10) 0.0008(9) C8 0.0303(12) 0.0313(13) 0.0455(15) 0.0042(11) 0.0003(11) -0.0030(10) C9 0.0350(11) 0.0423(12) 0.0327(12) 0.0053(14) 0.0021(9) -0.0002(12) C10 0.0338(12) 0.0362(14) 0.0260(13) -0.0012(10) 0.0028(10) 0.0034(10) C11 0.0659(16) 0.0436(14) 0.0402(14) 0.0134(12) 0.0106(13) -0.0002(13) C12 0.0361(13) 0.0385(15) 0.0584(17) -0.0108(12) -0.0015(11) -0.0008(11) C13 0.0339(12) 0.0324(12) 0.0531(15) -0.0005(10) -0.0002(12) 0.0039(10) _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 C9 1.835(2) . ? O1 C1 1.441(2) . ? O1 H1 0.8400 . ? C1 C10 1.527(3) . ? C1 C6 1.533(3) . ? C1 C2 1.538(3) . ? C2 C3 1.534(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C11 1.527(3) . ? C3 C4 1.528(3) . ? C3 H3 1.0000 . ? C4 C5 1.533(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.527(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.558(3) . ? C6 H6 1.0000 . ? C7 C13 1.527(3) . ? C7 C12 1.538(3) . ? C7 C8 1.545(3) . ? C8 C9 1.516(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.516(3) . ? C9 H9 1.0000 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? 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 C1 O1 H1 109.5 . . ? O1 C1 C10 110.04(16) . . ? O1 C1 C6 107.97(15) . . ? C10 C1 C6 110.74(16) . . ? O1 C1 C2 109.61(16) . . ? C10 C1 C2 108.68(16) . . ? C6 C1 C2 109.79(16) . . ? C3 C2 C1 115.22(16) . . ? C3 C2 H2A 108.5 . . ? C1 C2 H2A 108.5 . . ? C3 C2 H2B 108.5 . . ? C1 C2 H2B 108.5 . . ? H2A C2 H2B 107.5 . . ? C11 C3 C4 111.84(19) . . ? C11 C3 C2 114.51(18) . . ? C4 C3 C2 109.14(18) . . ? C11 C3 H3 107.0 . . ? C4 C3 H3 107.0 . . ? C2 C3 H3 107.0 . . ? C3 C4 C5 112.50(18) . . ? C3 C4 H4A 109.1 . . ? C5 C4 H4A 109.1 . . ? C3 C4 H4B 109.1 . . ? C5 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? C6 C5 C4 110.73(18) . . ? C6 C5 H5A 109.5 . . ? C4 C5 H5A 109.5 . . ? C6 C5 H5B 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? C5 C6 C1 110.51(17) . . ? C5 C6 C7 114.50(17) . . ? C1 C6 C7 114.62(16) . . ? C5 C6 H6 105.4 . . ? C1 C6 H6 105.4 . . ? C7 C6 H6 105.4 . . ? C13 C7 C12 107.48(17) . . ? C13 C7 C8 111.45(18) . . ? C12 C7 C8 105.61(18) . . ? C13 C7 C6 113.27(17) . . ? C12 C7 C6 109.67(17) . . ? C8 C7 C6 109.06(17) . . ? C9 C8 C7 117.55(17) . . ? C9 C8 H8A 107.9 . . ? C7 C8 H8A 107.9 . . ? C9 C8 H8B 107.9 . . ? C7 C8 H8B 107.9 . . ? H8A C8 H8B 107.2 . . ? C8 C9 C10 112.57(17) . . ? C8 C9 Cl1 112.24(14) . . ? C10 C9 Cl1 111.24(15) . . ? C8 C9 H9 106.8 . . ? C10 C9 H9 106.8 . . ? Cl1 C9 H9 106.8 . . ? C9 C10 C1 115.49(17) . . ? C9 C10 H10A 108.4 . . ? C1 C10 H10A 108.4 . . ? C9 C10 H10B 108.4 . . ? C1 C10 H10B 108.4 . . ? H10A C10 H10B 107.5 . . ? C3 C11 H11A 109.5 . . ? C3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C7 C13 H13A 109.5 . . ? C7 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C7 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? 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 -64.9(2) . . . . ? C10 C1 C2 C3 174.77(17) . . . . ? C6 C1 C2 C3 53.5(2) . . . . ? C1 C2 C3 C11 74.5(2) . . . . ? C1 C2 C3 C4 -51.7(2) . . . . ? C11 C3 C4 C5 -74.7(2) . . . . ? C2 C3 C4 C5 53.0(2) . . . . ? C3 C4 C5 C6 -58.3(3) . . . . ? C4 C5 C6 C1 58.7(2) . . . . ? C4 C5 C6 C7 -170.10(17) . . . . ? O1 C1 C6 C5 64.1(2) . . . . ? C10 C1 C6 C5 -175.35(17) . . . . ? C2 C1 C6 C5 -55.3(2) . . . . ? O1 C1 C6 C7 -67.1(2) . . . . ? C10 C1 C6 C7 53.5(2) . . . . ? C2 C1 C6 C7 173.48(17) . . . . ? C5 C6 C7 C13 -55.1(2) . . . . ? C1 C6 C7 C13 74.1(2) . . . . ? C5 C6 C7 C12 64.9(2) . . . . ? C1 C6 C7 C12 -165.84(16) . . . . ? C5 C6 C7 C8 -179.87(17) . . . . ? C1 C6 C7 C8 -50.6(2) . . . . ? C13 C7 C8 C9 -79.1(2) . . . . ? C12 C7 C8 C9 164.52(17) . . . . ? C6 C7 C8 C9 46.7(2) . . . . ? C7 C8 C9 C10 -45.3(2) . . . . ? C7 C8 C9 Cl1 81.1(2) . . . . ? C8 C9 C10 C1 46.4(2) . . . . ? Cl1 C9 C10 C1 -80.53(19) . . . . ? O1 C1 C10 C9 68.6(2) . . . . ? C6 C1 C10 C9 -50.7(2) . . . . ? C2 C1 C10 C9 -171.37(16) . . . . ? 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 O1 H1 Cl1 0.84 2.63 3.4516(18) 168.0 3_645 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.33 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.223 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.036 _publ_requested_category FO _publ_section_references ; Sheldrick, G.M. (2001). SHELX-97-2. Program for crystal structure solution and refinement. Institute fur anorg chemie, G\"ottingen, Germany. Bruker AXS, Inc. (2001). Madison, Wisconsin, USA. ; _publ_section_figure_captions ; Figure 1. SHELXTL (Bruker, 2001) plot showing 35% probability ellipsoids for non-H atoms and circles of arbitrary size for H atoms. ; _publ_section_exptl_prep ; Crystals were grown by evaporation from pentane. ; _publ_section_exptl_refinement ; Systematic conditions suggested the unambiguous space group. Structure was phased by direct methods (Sheldrick, 2001). Methyl H atom positions, R-CH~3~, were optimized by rotation about R-C bonds with idealized C-H, R--H and H--H distances. Hydroxyl H atom positions, R-OH, were optimized by rotation about R-O bonds with idealized O-H and R--H distances. Remaining H atoms were included as riding idealized contributors. Methyl and hydroxyl H atom U's were assigned as 1.5 times U~eq~ of adjacent atom; remaining H atom U's were assigned as 1.2 times adjacent U~eq~. The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F^2^ (Sheldrick, 2001). The highest peaks in the final difference Fourier map were in the vicinity of atoms Cl1, C9, and C1; the final map had no other significant features. A final analysis of variance between observed and calculated structure factors showed no dependence on amplitude or resolution. ; _publ_contact_author ; Scott R. Wilson University of Illinois School of Chemical Sciences, Box 59-1 505 South Mathews Avenue Urbana, Illinois 61801 USA ; _publ_contact_author_phone '1 217 244 1708' _publ_contact_author_fax '1 217 244 8068' _publ_contact_author_email srwilson@uiuc.edu _publ_contact_letter ; Please consider this CIF submission for publication as a structural paper in Acta Crystallographica C. The figure and list of structure factors will be sent by normal mail. ; _publ_requested_journal 'Acta Crystallographica C' _publ_requested_coeditor_name ? _publ_section_title ; ? ; _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_acknowledgements ; The Materials Chemistry Laboratory at the University of Illinois was supported in part by Grant No. NSF CHE 95-03145 from the National Science Foundation. ; loop_ _publ_author_name _publ_author_address 'Wilson, Scott R.' ; University of Illinois School of Chemical Sciences, Box 59-1 505 South Mathews Avenue Urbana, Illinois 61801 USA ; 'Prussak-Wieckowska, Teresa' ; University of Illinois School of Chemical Sciences, Box 59-1 505 South Mathews Avenue Urbana, Illinois 61801 USA ; loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 0.00 -1.00 0.0250 0.00 0.00 1.00 0.0250 1.00 1.00 1.00 0.2700 -1.00 0.00 2.00 0.2800 0.00 -2.00 1.00 0.0600 0.00 1.00 -1.00 0.0600 _exptl_crystal_recrystallization_method 'recrystallized from pentane at 0 C'