# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 #TrackingRef '- All.cif' _audit_creation_method SHELXL-97 # PROCESSING SUMMARY ( IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_coeditor_code ? # SUBMISSION DETAILS _publ_contact_author_name 'Andrzej Katrusiak' _publ_contact_author_address ; Faculty of Chemistry Adam Mickiewicz University Grunwaldzka 6 60-780 Pozna\'n Poland ; _publ_contact_author_email katran@amu.edu.pl _publ_contact_letter ; Please consider this CIF submission for publication in ??? ; _publ_requested_category FO _publ_requested_coeditor_name ? # TITLE AND AUTHOR LIST _publ_section_title ; ??? ; loop_ _publ_author_name _publ_author_address M.Podsiadlo ; Faculty of Chemistry Adam Mickiewicz University Grunwaldzka 6 60-780 Pozna\'n Poland ; E.Patyk ; Faculty of Chemistry Adam Mickiewicz University Grunwaldzka 6 60-780 Pozna\'n Poland ; A.Katrusiak ; Faculty of Chemistry Adam Mickiewicz University Grunwaldzka 6 60-780 Pozna\'n Poland ; ############################################################################# data_23butdiol_0.43GPa _database_code_depnum_ccdc_archive 'CCDC 870121' #TrackingRef '- All.cif' # CHEMICAL DATA _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,3-butanediol ; _chemical_name_common 2,3-butanediol _chemical_melting_point 298 _chemical_formula_moiety 'C4 H10 O2' _chemical_formula_sum 'C4 H10 O2' _chemical_formula_weight 90.12 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' # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _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 5.0482(10) _cell_length_b 9.4220(19) _cell_length_c 10.250(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 487.56(17) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3678 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 24.98 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 200 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.34 _exptl_absorpt_correction_T_max 0.87 _exptl_absorpt_process_details ; Correction for absorption of the diamond-anvil cell and the sample were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam Mickiewicz University Pozna\'n; Katrusiak, A. (2004) Z. Kristallogr. 219, 461-467). ; # EXPERIMENTAL DATA _exptl_special_details ; Data were collected at room temperature and pressure of 0.43(5) GPa (430000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line. ; _diffrn_ambient_temperature 295(2) _diffrn_ambient_environment 'diamond-anvil cell' _diffrn_ambient_pressure 430000 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KM-4 CCD' _diffrn_measurement_method '\f- and \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3678 _diffrn_reflns_av_R_equivalents 0.0642 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 24.98 _reflns_number_total 467 _reflns_number_gt 369 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisCCD (Oxford Diffraction, 2004)' _computing_cell_refinement 'CrysAlisRED (Oxford Diffraction, 2004)' _computing_data_reduction 'CrysAlisRED (Oxford Diffraction, 2004); REDSHABS (Katrusiak, A. 2003)' _computing_structure_solution 'SHELXS--97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL--97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1990)' _computing_publication_material 'SHELXL--97 (Sheldrick, 1997)' # REFINEMENT DATA _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. The DAC imposes severe restrictions on which reflections can be collected, resulting in a low data:parameter ratio. ; _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^)+(0.0603P)^2^+0.1760P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(6) _refine_ls_number_reflns 467 _refine_ls_number_parameters 55 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0619 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1333 _refine_ls_wR_factor_gt 0.1242 _refine_ls_goodness_of_fit_ref 1.126 _refine_ls_restrained_S_all 1.253 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 O1 O 0.3033(7) -0.0537(8) 0.2016(3) 0.073(3) Uani 1 1 d . . . H1 H 0.1592 -0.0938 0.1991 0.109 Uiso 1 1 calc R . . O2 O 0.1929(7) 0.3132(8) 0.2953(3) 0.058(3) Uani 1 1 d . . . H2 H 0.3432 0.3463 0.2972 0.070 Uiso 1 1 calc R . . C1 C 0.0637(9) 0.1267(10) 0.0789(4) 0.0559(19) Uani 1 1 d U . . H11 H 0.0849 0.0667 0.0040 0.084 Uiso 1 1 calc R . . H12 H 0.0856 0.2241 0.0536 0.084 Uiso 1 1 calc R . . H13 H -0.1101 0.1135 0.1149 0.084 Uiso 1 1 calc R . . C2 C 0.2691(9) 0.0888(11) 0.1800(4) 0.0388(16) Uani 1 1 d U . . H21 H 0.4388 0.1252 0.1479 0.047 Uiso 1 1 calc R . . C3 C 0.2038(10) 0.1743(11) 0.3141(5) 0.045(2) Uani 1 1 d U . . H31 H 0.3453 0.1545 0.3769 0.055 Uiso 1 1 calc R . . C4 C -0.0560(9) 0.1195(9) 0.3704(4) 0.0561(19) Uani 1 1 d U . . H41 H -0.1089 0.1785 0.4421 0.084 Uiso 1 1 calc R . . H42 H -0.0324 0.0238 0.4004 0.084 Uiso 1 1 calc R . . H43 H -0.1904 0.1215 0.3041 0.084 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 O1 0.0368(17) 0.111(10) 0.071(2) 0.005(3) -0.0063(17) -0.003(3) O2 0.0296(17) 0.065(11) 0.080(3) 0.000(3) -0.0065(18) -0.002(3) C1 0.049(2) 0.079(6) 0.039(2) -0.002(2) -0.0009(19) -0.009(3) C2 0.031(2) 0.043(4) 0.0423(18) 0.000(2) 0.0094(15) -0.011(3) C3 0.027(2) 0.067(6) 0.042(2) 0.001(3) -0.0061(18) -0.002(3) C4 0.042(2) 0.079(6) 0.047(2) -0.006(3) 0.0115(17) -0.002(3) # MOLECULAR GEOMETRY _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 O1 C2 1.372(10) . ? O1 H1 0.8200 . ? O2 C3 1.325(9) . ? O2 H2 0.8200 . ? C1 C2 1.509(7) . ? C1 H11 0.9600 . ? C1 H12 0.9600 . ? C1 H13 0.9600 . ? C2 C3 1.626(9) . ? C2 H21 0.9800 . ? C3 C4 1.523(8) . ? C3 H31 0.9800 . ? C4 H41 0.9600 . ? C4 H42 0.9600 . ? C4 H43 0.9600 . ? 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 C2 O1 H1 109.5 . . ? C3 O2 H2 109.5 . . ? C2 C1 H11 109.5 . . ? C2 C1 H12 109.5 . . ? H11 C1 H12 109.5 . . ? C2 C1 H13 109.5 . . ? H11 C1 H13 109.5 . . ? H12 C1 H13 109.5 . . ? O1 C2 C1 115.4(6) . . ? O1 C2 C3 112.0(5) . . ? C1 C2 C3 108.9(6) . . ? O1 C2 H21 106.7 . . ? C1 C2 H21 106.7 . . ? C3 C2 H21 106.7 . . ? O2 C3 C4 110.8(6) . . ? O2 C3 C2 112.0(5) . . ? C4 C3 C2 109.1(6) . . ? O2 C3 H31 108.3 . . ? C4 C3 H31 108.3 . . ? C2 C3 H31 108.3 . . ? C3 C4 H41 109.5 . . ? C3 C4 H42 109.5 . . ? H41 C4 H42 109.5 . . ? C3 C4 H43 109.5 . . ? H41 C4 H43 109.5 . . ? H42 C4 H43 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 C2 C3 O2 174.6(5) . . . . ? C1 C2 C3 O2 -56.5(6) . . . . ? O1 C2 C3 C4 -62.4(6) . . . . ? C1 C2 C3 C4 66.5(9) . . . . ? _diffrn_measured_fraction_theta_max 0.552 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.552 _refine_diff_density_max 0.156 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.035 # # h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag # loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_squared_calc _refln_F_squared_meas _refln_F_squared_sigma _refln_observed_status 2 0 0 1220.37 1270.38 2.12 o 4 0 0 87.45 96.35 1.64 o 6 0 0 0.26 0.59 1.53 o 1 1 0 1482.78 1564.73 21.72 o 2 1 0 246.22 228.37 2.66 o 3 1 0 145.97 166.25 3.03 o 4 1 0 166.30 167.74 1.47 o 5 1 0 5.80 5.03 1.13 o 2 2 0 1.28 0.34 0.53 o 3 2 0 16.37 14.67 0.78 o 4 2 0 2.08 1.58 0.59 o 5 2 0 1.28 2.92 1.40 o 3 3 0 9.59 7.77 1.92 o 4 3 0 0.01 2.38 1.82 o 5 3 0 4.38 4.30 4.64 o 1 0 1 741.25 716.16 3.84 o 2 0 1 45.59 37.11 0.37 o 3 0 1 0.30 0.91 0.25 o 4 0 1 203.50 210.82 3.38 o 5 0 1 1.69 3.72 1.10 o -5 1 1 7.60 9.23 1.24 o -4 1 1 62.92 59.85 1.39 o -3 1 1 139.94 144.70 2.06 o -2 1 1 388.17 430.07 5.90 o -1 1 1 1319.36 1352.55 23.87 o 0 1 1 91.15 83.22 1.81 o 1 1 1 1319.44 1329.79 22.06 o 2 1 1 388.34 436.55 6.67 o 3 1 1 140.01 146.68 2.02 o 4 1 1 62.92 64.29 1.37 o 5 1 1 7.62 8.82 1.53 o -5 2 1 108.53 116.83 3.30 o -4 2 1 16.16 21.51 1.35 o -3 2 1 382.58 415.22 3.18 o -2 2 1 121.49 122.12 1.71 o 2 2 1 121.52 122.62 3.34 o 3 2 1 383.04 407.36 5.20 o 4 2 1 16.15 20.42 1.14 o 5 2 1 108.31 108.55 4.74 o -5 3 1 5.55 3.87 1.32 o -4 3 1 2.78 2.37 1.01 o -3 3 1 2.16 2.23 1.54 o 3 3 1 2.20 0.85 0.82 o 4 3 1 2.80 2.76 2.02 o 5 3 1 5.57 5.59 2.59 o 0 0 2 3796.94 3656.76 70.56 o 1 0 2 211.05 229.93 0.80 o 2 0 2 1989.13 1964.16 27.64 o 3 0 2 92.63 95.22 1.72 o 4 0 2 47.16 50.42 1.27 o 5 0 2 58.29 67.21 1.68 o -5 1 2 24.05 22.68 1.46 o -4 1 2 133.69 128.71 1.89 o -3 1 2 157.84 146.84 2.33 o -2 1 2 308.96 293.52 4.36 o -1 1 2 433.21 423.30 7.46 o 0 1 2 556.95 563.91 2.77 o 1 1 2 433.26 414.23 5.36 o 2 1 2 308.63 292.29 6.38 o 3 1 2 157.76 146.94 2.38 o 4 1 2 133.66 129.76 1.69 o 5 1 2 24.05 23.54 1.52 o -5 2 2 0.38 0.32 1.15 o -4 2 2 31.93 36.17 1.76 o -3 2 2 64.13 61.81 2.20 o -2 2 2 200.94 219.85 3.92 o -1 2 2 817.42 787.79 2.81 o 1 2 2 817.03 784.10 3.71 o 2 2 2 200.92 214.26 3.00 o 3 2 2 64.21 59.01 6.20 o 4 2 2 31.96 36.20 2.66 o 5 2 2 0.38 0.35 1.00 o -5 3 2 1.48 0.86 1.56 o -4 3 2 1.74 1.09 0.91 o -3 3 2 32.68 35.32 2.91 o -2 3 2 25.74 16.80 2.78 o 3 3 2 32.57 34.45 8.40 o 4 3 2 1.73 1.18 3.48 o 5 3 2 1.48 0.83 1.66 o -5 4 2 28.27 23.73 3.08 o -4 4 2 1.85 1.32 1.26 o 1 0 3 609.58 624.43 7.79 o 2 0 3 366.78 351.34 5.95 o 3 0 3 43.38 48.52 1.25 o 4 0 3 331.91 326.73 4.97 o 5 0 3 4.81 4.24 0.84 o -5 1 3 17.57 20.25 1.39 o -4 1 3 20.76 18.70 1.32 o -3 1 3 70.75 80.11 1.38 o -2 1 3 151.47 147.10 2.77 o -1 1 3 375.89 367.68 3.10 o 0 1 3 1539.11 1482.50 13.53 o 1 1 3 375.61 383.38 8.24 o 2 1 3 151.55 149.55 3.89 o 3 1 3 70.79 78.50 1.32 o 4 1 3 20.73 18.66 1.16 o 5 1 3 17.57 20.17 1.37 o -5 2 3 34.90 36.96 2.44 o -4 2 3 0.90 0.19 0.77 o -3 2 3 66.20 67.52 4.57 o -2 2 3 39.17 38.96 0.78 o -1 2 3 62.86 65.48 1.11 o 0 2 3 1510.91 1585.93 29.77 o 1 2 3 62.82 65.75 1.79 o 2 2 3 39.13 35.09 1.17 o 3 2 3 66.21 61.63 5.75 o 4 2 3 0.89 0.20 0.72 o 5 2 3 34.80 34.97 1.88 o -5 3 3 2.29 3.18 1.54 o -4 3 3 11.75 12.59 2.21 o -3 3 3 28.72 32.04 1.11 o -2 3 3 58.58 46.17 1.28 o -1 3 3 92.31 95.53 2.93 o 0 3 3 3.49 1.96 0.68 o 1 3 3 92.12 95.69 1.87 o 2 3 3 58.68 48.01 1.51 o 3 3 3 28.73 31.98 1.83 o 4 3 3 11.78 12.17 2.58 o 5 3 3 2.30 4.57 3.88 o -5 4 3 11.19 7.25 1.62 o -4 4 3 7.16 1.24 1.85 o -3 4 3 15.21 9.48 1.18 o 0 0 4 91.13 85.15 1.99 o 1 0 4 4.92 4.47 0.28 o 2 0 4 248.12 257.71 4.16 o 3 0 4 44.53 41.95 1.28 o 4 0 4 0.06 0.02 0.62 o -5 1 4 25.92 24.36 1.84 o -4 1 4 14.98 16.27 1.09 o -3 1 4 70.27 70.06 1.46 o -2 1 4 368.78 395.21 5.94 o -1 1 4 225.72 226.70 3.71 o 0 1 4 411.64 394.25 1.55 o 1 1 4 225.80 231.88 8.76 o 2 1 4 368.91 404.94 8.97 o 3 1 4 70.36 72.08 1.77 o 4 1 4 14.93 16.48 1.08 o 5 1 4 25.91 29.60 1.81 o -5 2 4 0.11 0.23 1.23 o -4 2 4 17.60 17.04 2.13 o -3 2 4 87.63 75.44 6.48 o -2 2 4 2.45 2.81 0.48 o -1 2 4 997.86 962.23 7.77 o 0 2 4 3.42 2.45 0.45 o 1 2 4 997.48 965.32 15.76 o 2 2 4 2.45 2.28 0.46 o 3 2 4 87.72 80.36 4.01 o 4 2 4 17.58 18.17 2.52 o 5 2 4 0.11 0.21 1.24 o -5 3 4 8.92 6.30 1.69 o -4 3 4 3.53 3.53 1.61 o -3 3 4 39.65 33.74 1.67 o -2 3 4 13.38 11.80 0.83 o -1 3 4 64.61 67.00 5.20 o 0 3 4 75.61 59.99 1.47 o 1 3 4 64.75 64.99 3.04 o 2 3 4 13.35 11.45 0.95 o 3 3 4 39.68 36.19 1.72 o 4 3 4 3.52 3.17 1.05 o 5 3 4 8.90 9.89 2.39 o -5 4 4 5.00 1.79 1.84 o -4 4 4 1.04 2.62 2.22 o -3 4 4 23.98 28.20 1.14 o -2 4 4 18.47 13.98 0.73 o -1 4 4 0.98 0.86 0.86 o 1 4 4 0.98 0.08 0.79 o 2 4 4 18.49 14.05 1.11 o 3 4 4 24.05 25.34 2.48 o 4 4 4 1.03 0.87 1.36 o 1 0 5 1.06 2.16 0.60 o 2 0 5 494.87 503.35 6.13 o 4 0 5 97.28 91.66 2.72 o 5 0 5 0.14 0.01 1.11 o -5 1 5 14.97 16.18 2.13 o -4 1 5 15.67 20.17 1.42 o -3 1 5 92.44 92.93 1.51 o -2 1 5 146.66 140.42 2.36 o -1 1 5 19.41 27.01 5.04 o 0 1 5 536.52 550.06 5.88 o 1 1 5 19.37 29.31 4.37 o 2 1 5 146.84 137.30 2.83 o 3 1 5 92.36 93.36 1.67 o 4 1 5 15.65 20.08 1.23 o 5 1 5 14.98 15.70 1.93 o -5 2 5 4.02 3.66 1.47 o -4 2 5 10.25 13.80 1.20 o -3 2 5 36.13 43.09 1.69 o -2 2 5 29.20 26.13 0.92 o -1 2 5 1.32 0.76 0.82 o 0 2 5 140.29 139.45 3.51 o 1 2 5 1.32 2.47 0.57 o 2 2 5 29.18 26.93 0.93 o 3 2 5 36.12 40.60 2.02 o 4 2 5 10.24 13.78 1.15 o 5 2 5 4.02 5.63 1.89 o -5 3 5 3.03 3.14 1.44 o -4 3 5 30.89 37.20 2.63 o -3 3 5 55.57 56.21 3.69 o -2 3 5 7.71 6.09 0.78 o -1 3 5 4.68 5.10 0.44 o 0 3 5 1.54 0.15 0.35 o 1 3 5 4.64 4.82 0.47 o 2 3 5 7.70 7.02 0.88 o 3 3 5 55.36 56.93 4.20 o 4 3 5 30.91 29.62 4.12 o 5 3 5 3.03 3.20 1.47 o -5 4 5 4.57 2.28 2.08 o -4 4 5 6.26 3.19 4.12 o -3 4 5 0.24 0.02 0.70 o -2 4 5 14.59 12.26 1.42 o -1 4 5 31.32 46.79 8.05 o 0 4 5 0.79 0.65 0.73 o 1 4 5 31.35 30.32 12.30 o 2 4 5 14.59 11.92 1.58 o 3 4 5 0.23 0.02 1.19 o 4 4 5 6.25 3.55 2.12 o 5 4 5 4.56 4.49 4.06 o -4 5 5 0.81 1.15 1.04 o -3 5 5 14.49 15.90 1.20 o 0 0 6 109.47 117.01 2.04 o 1 0 6 0.56 2.24 0.41 o 2 0 6 199.42 240.40 11.59 o 3 0 6 6.85 7.36 0.93 o 4 0 6 7.34 5.90 1.63 o 5 0 6 1.53 2.67 1.52 o -5 1 6 16.88 15.90 3.20 o -4 1 6 29.53 31.49 1.79 o -3 1 6 106.56 113.98 1.76 o -2 1 6 23.15 18.70 0.92 o -1 1 6 54.20 51.67 3.36 o 0 1 6 399.42 419.10 11.29 o 1 1 6 54.25 52.31 2.51 o 2 1 6 23.19 19.33 1.84 o 3 1 6 106.63 116.17 2.01 o 4 1 6 29.50 31.81 1.53 o 5 1 6 16.89 15.16 2.51 o -5 2 6 1.34 2.59 1.69 o -4 2 6 14.68 12.57 1.53 o -3 2 6 49.22 48.47 1.88 o -2 2 6 1.04 1.25 0.50 o -1 2 6 229.51 252.61 5.31 o 0 2 6 0.91 1.21 0.48 o 1 2 6 229.74 254.70 7.61 o 2 2 6 1.03 1.94 0.62 o 3 2 6 49.16 49.70 2.24 o 4 2 6 14.66 14.13 1.81 o 5 2 6 1.34 1.96 1.52 o -4 3 6 1.44 2.96 1.07 o -3 3 6 25.31 19.36 1.59 o -2 3 6 17.95 18.27 1.26 o -1 3 6 39.84 46.88 1.39 o 0 3 6 13.52 15.08 0.81 o 1 3 6 39.88 42.79 2.83 o 2 3 6 17.94 18.44 1.01 o 3 3 6 25.42 23.00 1.71 o 4 3 6 1.44 2.92 1.17 o -4 4 6 2.58 4.07 1.28 o -3 4 6 6.86 7.25 1.85 o -2 4 6 28.19 26.48 1.78 o -1 4 6 1.92 2.15 0.71 o 0 4 6 1.11 1.51 0.66 o 1 4 6 1.92 2.07 0.99 o 2 4 6 28.17 27.19 2.02 o 3 4 6 6.85 7.98 1.16 o 4 4 6 2.57 1.85 2.60 o -4 5 6 11.77 6.94 2.21 o -3 5 6 33.50 18.74 0.97 o -2 5 6 3.00 2.61 0.59 o -1 5 6 1.82 5.65 1.84 o 0 5 6 6.74 1.59 2.38 o 1 5 6 1.83 0.38 1.14 o 2 5 6 2.99 2.62 0.88 o 1 0 7 15.61 14.76 1.00 o 2 0 7 32.47 32.29 0.99 o 3 0 7 11.87 13.79 1.33 o 4 0 7 45.96 50.31 2.16 o -4 1 7 7.22 6.98 1.66 o -3 1 7 31.42 30.93 3.48 o -2 1 7 97.29 105.06 2.55 o -1 1 7 88.96 93.93 2.62 o 0 1 7 8.67 3.77 0.80 o 1 1 7 88.92 93.69 3.13 o 2 1 7 97.20 96.12 3.58 o 3 1 7 31.40 34.72 1.77 o 4 1 7 7.22 8.19 1.34 o -4 2 7 7.92 6.71 1.34 o -3 2 7 22.54 23.87 1.68 o -2 2 7 58.39 54.45 2.36 o -1 2 7 14.16 11.70 1.00 o 0 2 7 0.00 0.31 0.53 o 1 2 7 14.16 11.51 1.27 o 2 2 7 58.39 57.74 3.03 o 3 2 7 22.53 22.09 3.19 o 4 2 7 7.92 5.37 1.25 o -4 3 7 4.42 3.22 1.21 o -3 3 7 4.68 4.89 1.37 o -2 3 7 19.72 22.97 1.74 o -1 3 7 49.88 54.13 1.74 o 0 3 7 10.25 8.81 1.10 o 1 3 7 49.78 56.27 1.76 o 2 3 7 19.75 21.36 1.47 o 3 3 7 4.63 3.12 1.41 o 4 3 7 4.42 3.96 1.43 o -4 4 7 0.70 1.33 1.20 o -3 4 7 5.36 5.17 1.69 o -2 4 7 0.55 0.28 1.20 o -1 4 7 44.92 44.51 1.81 o 0 4 7 1.59 3.16 0.77 o 1 4 7 44.83 44.45 1.72 o 2 4 7 0.55 0.37 0.86 o 3 4 7 5.39 5.20 1.92 o 4 4 7 0.70 3.46 2.09 o -4 5 7 3.89 4.21 2.80 o -3 5 7 8.95 5.35 1.17 o -2 5 7 5.40 2.49 0.77 o -1 5 7 13.52 7.01 0.64 o 0 5 7 16.26 11.45 0.89 o 1 5 7 13.48 7.05 1.13 o 2 5 7 5.40 2.39 0.65 o 3 5 7 8.95 4.88 1.35 o 4 5 7 3.89 3.60 2.93 o 0 0 8 233.99 279.39 9.87 o 1 0 8 1.27 1.86 0.57 o 2 0 8 151.12 163.26 3.56 o 3 0 8 5.48 4.23 1.45 o 4 0 8 7.88 7.83 1.62 o -4 1 8 1.69 2.93 1.23 o -3 1 8 3.20 3.54 0.84 o -2 1 8 44.33 48.30 1.83 o -1 1 8 89.98 96.00 3.18 o 0 1 8 36.62 44.05 1.76 o 1 1 8 90.05 96.00 3.39 o 2 1 8 44.23 48.45 2.01 o 3 1 8 3.20 3.11 1.20 o 4 1 8 1.67 2.70 1.18 o -4 2 8 1.17 0.95 1.57 o -3 2 8 5.04 4.58 1.53 o -2 2 8 10.35 10.76 1.54 o -1 2 8 12.68 12.59 1.66 o 0 2 8 0.84 1.18 0.71 o 1 2 8 12.68 10.24 1.62 o 2 2 8 10.35 9.17 1.21 o 3 2 8 5.02 4.75 1.45 o 4 2 8 1.17 0.76 1.03 o -4 3 8 9.69 8.85 1.54 o -3 3 8 2.56 1.87 1.55 o -2 3 8 4.86 5.46 1.38 o -1 3 8 12.72 12.27 1.42 o 0 3 8 18.45 16.13 2.04 o 1 3 8 12.78 9.26 1.52 o 2 3 8 4.88 6.57 1.65 o 3 3 8 2.56 1.87 1.45 o 4 3 8 9.69 9.05 1.53 o -3 4 8 2.77 1.95 1.50 o -2 4 8 10.89 9.08 2.25 o -1 4 8 1.74 4.57 1.38 o 0 4 8 4.25 5.60 1.09 o 1 4 8 1.75 1.80 0.82 o 2 4 8 10.88 9.46 1.61 o 3 4 8 2.80 4.16 2.56 o -3 5 8 2.89 3.52 1.46 o -2 5 8 16.64 14.31 1.65 o -1 5 8 16.44 13.55 1.54 o 0 5 8 1.91 3.96 0.98 o 1 5 8 16.48 11.79 3.08 o 2 5 8 16.67 14.48 2.38 o 3 5 8 2.88 3.39 2.09 o 1 0 9 1.61 1.53 0.58 o 2 0 9 0.02 0.32 0.79 o 3 0 9 0.21 1.01 1.31 o -4 1 9 23.05 26.39 3.74 o -3 1 9 2.58 3.31 1.76 o -2 1 9 0.79 4.01 1.89 o -1 1 9 47.73 53.53 1.87 o 0 1 9 15.84 14.13 1.31 o 1 1 9 47.73 55.54 2.10 o 2 1 9 0.77 4.33 1.69 o 3 1 9 2.57 3.24 1.50 o 4 1 9 23.04 27.75 2.41 o -3 2 9 15.60 14.27 2.23 o -2 2 9 1.74 3.27 1.23 o -1 2 9 5.62 4.57 1.29 o 0 2 9 2.09 4.08 0.83 o 1 2 9 5.60 4.47 1.44 o 2 2 9 1.74 3.45 1.35 o 3 2 9 15.57 15.44 2.69 o -3 3 9 11.85 9.54 1.88 o -2 3 9 12.76 11.71 1.78 o -1 3 9 0.35 0.32 1.59 o 0 3 9 21.81 28.03 3.09 o 1 3 9 0.35 0.35 0.85 o 2 3 9 12.77 8.99 2.20 o 3 3 9 11.85 8.94 1.84 o -3 4 9 9.73 10.94 1.85 o -2 4 9 0.34 0.32 1.35 o -1 4 9 20.87 24.54 3.07 o 0 4 9 1.04 1.25 1.71 o 1 4 9 20.88 19.21 2.01 o 2 4 9 0.34 0.21 1.45 o 3 4 9 9.73 10.88 1.94 o -3 5 9 0.38 3.49 2.19 o -2 5 9 5.97 5.48 1.97 o -1 5 9 16.33 13.81 2.42 o 0 5 9 0.47 2.95 2.16 o 1 5 9 16.34 13.65 3.05 o 2 5 9 5.96 2.41 2.58 o 3 5 9 0.38 2.09 3.35 o -2 6 9 1.15 1.21 1.84 o -1 6 9 3.10 1.35 1.31 o 0 6 9 3.89 1.71 1.16 o 1 6 9 3.09 1.40 2.44 o 0 0 10 58.95 50.14 8.15 o 1 0 10 2.32 1.83 0.85 o 2 0 10 26.20 17.76 8.67 o 3 0 10 0.70 5.86 3.81 o -3 1 10 7.93 6.93 1.82 o -2 1 10 9.82 11.52 1.98 o -1 1 10 19.99 28.82 2.54 o 0 1 10 25.06 26.57 2.70 o 1 1 10 19.96 29.02 2.06 o 2 1 10 9.83 13.37 2.44 o 3 1 10 7.94 9.25 2.32 o -3 2 10 1.29 2.60 1.77 o -2 2 10 1.20 2.17 1.30 o -1 2 10 2.81 3.36 1.19 o 0 2 10 0.01 0.10 2.58 o 1 2 10 2.81 2.63 1.21 o 2 2 10 1.20 3.41 1.98 o 3 2 10 1.29 2.32 1.56 o -3 3 10 2.48 1.91 1.52 o -2 3 10 12.61 14.75 2.19 o -1 3 10 9.11 8.43 1.50 o 0 3 10 1.80 1.68 1.34 o 1 3 10 9.06 11.17 1.46 o 2 3 10 12.60 16.41 2.30 o 3 3 10 2.49 4.13 1.81 o -2 4 10 0.66 0.60 1.46 o -1 4 10 2.56 2.82 1.14 o 0 4 10 0.53 2.21 1.27 o 1 4 10 2.57 3.32 2.08 o 2 4 10 0.65 0.65 1.81 o -2 5 10 2.26 1.59 1.46 o -1 5 10 5.37 7.96 2.31 o 0 5 10 38.21 37.56 3.27 o 1 5 10 5.35 6.39 2.30 o 2 5 10 2.26 2.14 2.64 o -1 6 10 6.87 1.61 1.84 o 0 6 10 0.37 1.51 1.65 o 1 6 10 6.87 2.93 2.18 o -2 1 11 9.08 8.71 2.27 o -1 1 11 3.03 5.69 1.62 o 0 1 11 2.67 1.52 1.39 o 1 1 11 3.04 6.33 1.60 o 2 1 11 9.10 9.86 2.01 o -2 2 11 0.63 0.46 1.68 o -1 2 11 0.21 1.99 1.45 o 0 2 11 6.22 4.92 1.62 o 1 2 11 0.21 2.09 1.21 o 2 2 11 0.62 0.38 1.62 o -2 3 11 1.36 2.45 1.61 o -1 3 11 7.76 7.30 1.66 o 0 3 11 20.70 17.52 2.95 o 1 3 11 7.77 7.30 1.69 o 2 3 11 1.37 5.26 2.31 o -1 4 11 9.09 6.21 1.82 o 1 4 11 9.09 6.21 1.98 o 0 1 12 1.01 0.62 1.26 o ################################################################## data_23butdiol_0.63GPa _database_code_depnum_ccdc_archive 'CCDC 870122' #TrackingRef '- All.cif' # CHEMICAL DATA _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,3-butanediol ; _chemical_name_common 2,3-butanediol _chemical_melting_point 298 _chemical_formula_moiety 'C4 H10 O2' _chemical_formula_sum 'C4 H10 O2' _chemical_formula_weight 90.12 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' # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _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 5.0292(10) _cell_length_b 9.3989(19) _cell_length_c 10.186(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 481.46(17) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3408 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 24.96 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 200 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.34 _exptl_absorpt_correction_T_max 0.87 _exptl_absorpt_process_details ; Correction for absorption of the diamond-anvil cell and the sample were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam Mickiewicz University Pozna\'n; Katrusiak, A. (2004) Z. Kristallogr. 219, 461-467). ; # EXPERIMENTAL DATA _exptl_special_details ; Data were collected at room temperature and pressure of 0.63(5) GPa (630000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line. ; _diffrn_ambient_temperature 295(2) _diffrn_ambient_environment 'diamond-anvil cell' _diffrn_ambient_pressure 630000 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KM-4 CCD' _diffrn_measurement_method '\f- and \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3408 _diffrn_reflns_av_R_equivalents 0.1126 _diffrn_reflns_av_sigmaI/netI 0.0531 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 24.96 _reflns_number_total 432 _reflns_number_gt 315 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisCCD (Oxford Diffraction, 2004)' _computing_cell_refinement 'CrysAlisRED (Oxford Diffraction, 2004)' _computing_data_reduction 'CrysAlisRED (Oxford Diffraction, 2004); REDSHABS (Katrusiak, A. 2003)' _computing_structure_solution 'SHELXS--97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL--97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1990)' _computing_publication_material 'SHELXL--97 (Sheldrick, 1997)' # REFINEMENT DATA _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. The DAC imposes severe restrictions on which reflections can be collected, resulting in a low data:parameter ratio. The relatively high R factors are due to the low quality of the crystal sample. Generally it was difficult to grow single crystals of this substance, and in this case we increased pressure from the previous experiment at 0.43 GPa to 0.63 GPa without melting the crystal. In the next experiments we performed all crystallization again to obtain better quality samples. ; _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^)+(0.1970P)^2^+0.2270P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2(10) _refine_ls_number_reflns 432 _refine_ls_number_parameters 55 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.1224 _refine_ls_R_factor_gt 0.1013 _refine_ls_wR_factor_ref 0.3079 _refine_ls_wR_factor_gt 0.2764 _refine_ls_goodness_of_fit_ref 1.157 _refine_ls_restrained_S_all 1.262 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 O1 O 0.3021(14) -0.0553(14) 0.2008(5) 0.050(2) Uani 1 1 d U . . H1 H 0.1565 -0.0944 0.1981 0.075 Uiso 1 1 calc R . . O2 O 0.1908(13) 0.3147(14) 0.2968(6) 0.042(2) Uani 1 1 d U . . H2 H 0.3404 0.3492 0.2985 0.050 Uiso 1 1 calc R . . C1 C 0.0627(19) 0.130(2) 0.0762(9) 0.051(3) Uani 1 1 d U . . H11 H 0.0821 0.0703 0.0003 0.077 Uiso 1 1 calc R . . H12 H 0.0901 0.2274 0.0517 0.077 Uiso 1 1 calc R . . H13 H -0.1129 0.1187 0.1117 0.077 Uiso 1 1 calc R . . C2 C 0.2711(15) 0.0864(18) 0.1812(6) 0.025(2) Uani 1 1 d U . . H21 H 0.4428 0.1215 0.1493 0.030 Uiso 1 1 calc R . . C3 C 0.2070(18) 0.175(2) 0.3120(7) 0.031(3) Uani 1 1 d U . . H31 H 0.3494 0.1560 0.3752 0.038 Uiso 1 1 calc R . . C4 C -0.0574(18) 0.1148(19) 0.3707(9) 0.048(3) Uani 1 1 d U . . H41 H -0.1129 0.1733 0.4430 0.072 Uiso 1 1 calc R . . H42 H -0.0287 0.0193 0.4009 0.072 Uiso 1 1 calc R . . H43 H -0.1929 0.1150 0.3043 0.072 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 O1 0.039(3) 0.053(4) 0.059(3) 0.007(3) -0.006(2) -0.005(3) O2 0.028(3) 0.042(4) 0.056(3) -0.003(3) 0.003(2) -0.002(3) C1 0.042(4) 0.059(7) 0.053(4) 0.009(4) -0.001(3) -0.004(5) C2 0.020(3) 0.025(4) 0.029(3) -0.004(3) 0.003(2) -0.002(3) C3 0.022(3) 0.034(4) 0.038(3) 0.002(3) -0.005(2) 0.000(3) C4 0.036(4) 0.059(7) 0.050(4) -0.005(4) 0.007(3) -0.002(5) # MOLECULAR GEOMETRY _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 O1 C2 1.356(17) . ? O1 H1 0.8200 . ? O2 C3 1.324(14) . ? O2 H2 0.8200 . ? C1 C2 1.552(13) . ? C1 H11 0.9600 . ? C1 H12 0.9600 . ? C1 H13 0.9600 . ? C2 C3 1.604(16) . ? C2 H21 0.9800 . ? C3 C4 1.564(16) . ? C3 H31 0.9800 . ? C4 H41 0.9600 . ? C4 H42 0.9600 . ? C4 H43 0.9600 . ? 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 C2 O1 H1 109.5 . . ? C3 O2 H2 109.5 . . ? C2 C1 H11 109.5 . . ? C2 C1 H12 109.5 . . ? H11 C1 H12 109.5 . . ? C2 C1 H13 109.5 . . ? H11 C1 H13 109.5 . . ? H12 C1 H13 109.5 . . ? O1 C2 C1 115.9(9) . . ? O1 C2 C3 114.3(8) . . ? C1 C2 C3 107.5(10) . . ? O1 C2 H21 106.1 . . ? C1 C2 H21 106.1 . . ? C3 C2 H21 106.1 . . ? O2 C3 C4 110.6(11) . . ? O2 C3 C2 115.5(9) . . ? C4 C3 C2 107.5(11) . . ? O2 C3 H31 107.7 . . ? C4 C3 H31 107.7 . . ? C2 C3 H31 107.7 . . ? C3 C4 H41 109.5 . . ? C3 C4 H42 109.5 . . ? H41 C4 H42 109.5 . . ? C3 C4 H43 109.5 . . ? H41 C4 H43 109.5 . . ? H42 C4 H43 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 C2 C3 O2 176.3(8) . . . . ? C1 C2 C3 O2 -53.5(11) . . . . ? O1 C2 C3 C4 -59.8(11) . . . . ? C1 C2 C3 C4 70.4(14) . . . . ? _diffrn_measured_fraction_theta_max 0.521 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.521 _refine_diff_density_max 0.419 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.085 # # h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag # loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_squared_calc _refln_F_squared_meas _refln_F_squared_sigma _refln_observed_status 2 0 0 1232.48 1510.93 5.87 o 4 0 0 98.33 134.61 4.08 o 1 1 0 1451.22 1700.96 11.31 o 2 1 0 243.59 350.54 3.00 o 3 1 0 172.68 231.69 2.24 o 4 1 0 156.64 216.96 3.85 o 5 1 0 11.71 11.90 2.67 o 2 2 0 0.80 0.21 1.89 o 3 2 0 24.51 26.24 2.11 o 4 2 0 5.39 5.75 1.89 o 5 2 0 3.77 5.11 3.09 o 4 3 0 0.00 1.36 2.35 o 5 3 0 7.98 5.47 7.93 o 1 0 1 720.68 833.52 33.54 o 2 0 1 52.98 65.65 1.82 o 3 0 1 0.64 1.71 0.56 o 4 0 1 229.14 331.21 4.92 o 5 0 1 1.20 2.40 2.91 o -5 1 1 8.53 17.22 3.12 o -4 1 1 62.22 106.99 3.70 o -3 1 1 141.53 222.14 2.15 o -2 1 1 432.38 554.39 2.96 o -1 1 1 1313.35 1370.44 29.50 o 0 1 1 83.24 72.89 1.54 o 1 1 1 1313.40 1406.84 34.85 o 2 1 1 432.57 562.51 2.40 o 3 1 1 141.59 217.84 2.19 o 4 1 1 62.21 101.54 3.48 o 5 1 1 8.55 17.88 3.24 o -5 2 1 121.92 178.37 6.98 o -4 2 1 25.63 28.30 3.07 o -3 2 1 405.80 473.65 4.08 o -2 2 1 126.61 103.52 3.38 o 2 2 1 126.65 103.54 5.99 o 3 2 1 406.30 470.05 4.06 o 4 2 1 25.62 26.76 2.15 o 5 2 1 121.67 181.77 6.96 o -5 3 1 7.05 16.22 8.62 o -4 3 1 2.78 0.43 2.11 o -3 3 1 2.28 2.80 9.86 o 3 3 1 2.32 0.87 2.31 o 4 3 1 2.81 0.22 4.74 o 5 3 1 7.08 5.25 5.71 o 0 0 2 3826.03 4267.95 174.66 o 1 0 2 200.13 240.04 5.91 o 2 0 2 2065.22 2561.21 78.08 o 3 0 2 102.34 151.31 4.55 o 4 0 2 53.24 87.51 3.25 o 5 0 2 69.63 80.11 4.34 o -5 1 2 32.72 34.58 3.20 o -4 1 2 143.48 173.78 5.14 o -3 1 2 183.19 256.15 12.67 o -2 1 2 343.12 425.09 26.27 o -1 1 2 455.19 473.06 19.68 o 0 1 2 549.83 517.01 4.88 o 1 1 2 455.22 448.61 24.22 o 2 1 2 342.74 395.12 30.16 o 3 1 2 183.09 259.41 11.54 o 4 1 2 143.44 168.81 4.02 o 5 1 2 32.72 34.38 3.59 o -5 2 2 1.32 5.46 2.60 o -4 2 2 41.36 39.11 3.16 o -3 2 2 76.90 85.94 5.95 o -2 2 2 211.55 266.71 10.24 o -1 2 2 930.21 826.30 24.00 o 0 2 2 0.70 1.12 1.18 o 1 2 2 929.76 865.49 28.45 o 2 2 2 211.53 273.82 14.22 o 3 2 2 76.99 94.40 12.26 o 4 2 2 41.42 46.01 3.49 o 5 2 2 1.32 4.43 2.18 o -5 3 2 1.85 5.80 4.87 o -4 3 2 2.85 6.36 2.26 o -3 3 2 34.93 51.36 5.49 o -2 3 2 32.67 18.37 9.49 o 3 3 2 34.81 34.89 20.48 o 4 3 2 2.84 2.22 2.93 o 5 3 2 1.84 6.91 5.94 o 1 0 3 544.90 563.74 2.70 o 2 0 3 390.54 459.97 16.56 o 3 0 3 55.98 70.43 1.93 o 4 0 3 358.19 503.83 5.33 o 5 0 3 7.32 7.53 2.04 o -5 1 3 21.24 28.97 3.05 o -4 1 3 20.88 28.63 4.67 o -3 1 3 65.99 85.16 2.13 o -2 1 3 163.90 144.30 5.88 o -1 1 3 412.35 448.63 4.69 o 0 1 3 1687.21 1540.17 8.12 o 1 1 3 412.07 454.47 4.33 o 2 1 3 164.03 149.84 10.05 o 3 1 3 66.05 89.10 2.71 o 4 1 3 20.86 29.04 3.28 o 5 1 3 21.26 27.90 3.00 o -5 2 3 38.44 55.42 6.47 o -4 2 3 2.76 3.64 1.60 o -3 2 3 66.06 78.11 2.79 o -2 2 3 45.18 46.37 1.23 o -1 2 3 64.39 65.06 2.51 o 0 2 3 1511.64 1455.77 28.51 o 1 2 3 64.34 61.67 3.46 o 2 2 3 45.13 47.95 2.48 o 3 2 3 66.06 73.55 3.20 o 4 2 3 2.75 4.97 1.92 o 5 2 3 38.33 48.40 4.56 o -5 3 3 2.81 5.09 4.84 o -4 3 3 17.07 17.92 5.51 o -3 3 3 33.65 33.26 2.78 o -2 3 3 68.29 60.88 2.74 o -1 3 3 85.84 65.77 8.12 o 0 3 3 16.12 9.38 2.27 o 1 3 3 85.66 65.53 7.46 o 2 3 3 68.43 58.54 3.16 o 3 3 3 33.65 31.99 3.25 o 4 3 3 17.11 7.25 4.65 o 5 3 3 2.84 5.52 4.56 o -5 4 3 21.56 7.41 8.98 o -4 4 3 12.41 11.97 2.76 o -3 4 3 18.60 20.48 3.37 o 0 0 4 57.95 85.90 4.81 o 1 0 4 6.01 1.75 0.67 o 2 0 4 233.66 259.27 12.46 o 3 0 4 47.23 51.01 2.14 o 4 0 4 0.02 0.45 1.37 o 5 0 4 1.59 1.13 2.03 o -5 1 4 38.91 54.93 3.89 o -4 1 4 18.09 14.74 2.51 o -3 1 4 79.69 81.83 2.71 o -2 1 4 431.59 428.01 16.49 o -1 1 4 241.35 253.26 4.10 o 0 1 4 524.59 356.33 4.68 o 1 1 4 241.43 256.04 6.26 o 2 1 4 431.76 418.09 10.58 o 3 1 4 79.79 82.86 3.12 o 4 1 4 18.03 16.37 2.34 o 5 1 4 38.90 53.93 4.57 o -5 2 4 1.54 2.60 3.39 o -4 2 4 19.66 24.30 4.34 o -3 2 4 110.71 109.17 3.68 o -2 2 4 2.09 1.81 0.81 o -1 2 4 1155.97 975.98 33.91 o 0 2 4 3.15 0.39 1.19 o 1 2 4 1155.67 919.93 55.98 o 2 2 4 2.12 1.83 0.72 o 3 2 4 110.83 111.63 4.55 o 4 2 4 19.63 22.28 5.21 o 5 2 4 1.54 2.54 2.97 o -5 3 4 8.61 13.24 4.56 o -4 3 4 8.01 8.79 3.76 o -3 3 4 44.09 43.00 3.80 o -2 3 4 22.10 23.18 2.57 o -1 3 4 64.24 94.59 15.66 o 0 3 4 79.22 52.17 2.90 o 1 3 4 64.39 68.92 10.33 o 2 3 4 22.05 21.95 1.79 o 3 3 4 44.11 41.16 4.81 o 4 3 4 8.00 7.84 2.78 o 5 3 4 8.58 7.11 4.88 o -5 4 4 5.16 16.42 10.77 o -4 4 4 0.88 18.50 18.76 o -3 4 4 29.71 19.18 5.78 o -2 4 4 21.46 5.52 2.84 o 2 4 4 21.48 8.31 4.13 o 3 4 4 29.79 19.68 8.27 o 1 0 5 6.25 13.59 1.67 o 2 0 5 521.52 580.00 22.01 o 3 0 5 0.99 3.34 0.98 o 4 0 5 120.50 134.56 7.74 o 5 0 5 0.00 0.18 3.40 o -5 1 5 18.22 23.48 4.37 o -4 1 5 13.80 21.45 2.88 o -3 1 5 101.56 134.12 3.46 o -2 1 5 181.62 145.44 8.63 o -1 1 5 13.51 11.54 2.31 o 0 1 5 620.67 570.60 2.41 o 1 1 5 13.48 12.02 3.34 o 2 1 5 181.83 146.39 8.69 o 3 1 5 101.50 139.23 3.32 o 4 1 5 13.78 16.87 3.24 o 5 1 5 18.24 23.80 4.19 o -5 2 5 5.55 6.34 3.52 o -4 2 5 9.30 6.21 3.62 o -3 2 5 35.92 48.85 5.06 o -2 2 5 26.10 30.04 2.21 o -1 2 5 1.91 1.24 1.21 o 0 2 5 119.01 110.05 12.17 o 1 2 5 1.91 3.17 1.55 o 2 2 5 26.09 29.75 2.14 o 3 2 5 35.91 51.42 5.01 o 4 2 5 9.31 9.05 2.99 o 5 2 5 5.56 7.20 4.63 o -5 3 5 3.02 6.63 3.75 o -4 3 5 32.83 26.91 5.90 o -3 3 5 62.97 77.25 6.19 o -2 3 5 6.50 4.34 1.36 o -1 3 5 2.88 3.07 0.75 o 0 3 5 3.19 1.57 0.60 o 1 3 5 2.84 3.16 0.86 o 2 3 5 6.48 7.91 1.82 o 3 3 5 62.71 68.12 4.76 o 4 3 5 32.86 27.55 4.73 o 5 3 5 3.03 2.40 3.32 o -5 4 5 12.04 5.69 6.03 o -4 4 5 6.73 4.18 5.58 o -3 4 5 1.22 1.89 2.25 o -2 4 5 17.48 20.78 2.92 o -1 4 5 49.29 70.66 7.38 o 0 4 5 3.08 1.31 1.87 o 1 4 5 49.27 54.29 12.27 o 2 4 5 17.48 16.57 3.17 o 3 4 5 1.20 3.43 4.99 o 4 4 5 6.73 4.24 4.70 o 0 0 6 167.52 128.10 7.10 o 1 0 6 0.85 0.56 0.93 o 2 0 6 230.87 238.09 3.48 o 3 0 6 7.44 4.57 1.45 o 4 0 6 17.04 10.06 2.86 o 5 0 6 0.18 7.67 3.79 o -5 1 6 24.49 37.06 5.34 o -4 1 6 29.47 37.56 3.71 o -3 1 6 118.42 138.71 4.87 o -2 1 6 32.62 16.63 2.17 o -1 1 6 65.46 50.48 4.47 o 0 1 6 495.96 442.15 3.58 o 1 1 6 65.52 56.35 3.67 o 2 1 6 32.67 9.46 2.25 o 3 1 6 118.50 145.67 8.84 o 4 1 6 29.45 37.93 2.79 o 5 1 6 24.51 41.14 4.59 o -5 2 6 0.36 1.03 3.67 o -4 2 6 16.16 24.44 3.86 o -3 2 6 62.21 59.17 3.70 o -2 2 6 3.43 3.54 1.34 o -1 2 6 295.13 234.84 9.49 o 0 2 6 1.71 0.14 1.03 o 1 2 6 295.39 240.10 9.21 o 2 2 6 3.42 2.66 1.23 o 3 2 6 62.17 59.05 3.56 o 4 2 6 16.14 24.41 3.40 o 5 2 6 0.36 0.94 3.69 o -4 3 6 3.16 5.88 2.62 o -3 3 6 21.03 25.62 3.58 o -2 3 6 17.97 13.80 2.54 o -1 3 6 56.27 47.13 3.45 o 0 3 6 12.53 10.64 2.59 o 1 3 6 56.34 52.40 3.06 o 2 3 6 17.96 11.69 2.50 o 3 3 6 21.15 16.72 3.50 o 4 3 6 3.16 3.31 2.73 o -4 4 6 3.65 3.11 3.50 o -3 4 6 5.10 6.18 3.70 o -2 4 6 27.28 29.51 3.94 o -1 4 6 3.58 2.36 1.20 o 0 4 6 2.61 4.07 1.26 o 1 4 6 3.58 2.81 1.50 o 2 4 6 27.26 24.37 3.51 o 3 4 6 5.08 4.79 3.53 o 4 4 6 3.63 3.65 5.34 o -3 5 6 53.82 40.47 5.66 o 1 0 7 12.16 11.84 1.92 o 2 0 7 47.10 38.90 2.28 o 3 0 7 7.88 5.94 2.36 o 4 0 7 56.53 62.13 4.85 o -4 1 7 12.95 14.43 3.16 o -3 1 7 36.61 33.38 3.61 o -2 1 7 108.36 109.39 6.82 o -1 1 7 111.66 123.03 3.54 o 0 1 7 28.11 6.47 2.08 o 1 1 7 111.61 112.76 3.45 o 2 1 7 108.24 107.79 10.73 o 3 1 7 36.60 32.48 4.39 o 4 1 7 12.94 11.67 2.91 o -4 2 7 12.21 11.08 2.89 o -3 2 7 28.70 28.26 4.12 o -2 2 7 46.03 56.88 6.44 o -1 2 7 15.74 11.21 2.75 o 0 2 7 0.00 3.55 1.25 o 1 2 7 15.73 10.91 2.22 o 2 2 7 46.05 59.21 4.63 o 3 2 7 28.69 23.54 3.61 o 4 2 7 12.22 7.92 2.78 o -4 3 7 3.18 7.78 2.61 o -3 3 7 5.14 5.92 2.95 o -2 3 7 20.51 25.94 2.96 o -1 3 7 52.30 41.74 3.23 o 0 3 7 6.83 8.35 1.95 o 1 3 7 52.16 42.39 3.51 o 2 3 7 20.55 25.75 4.26 o 3 3 7 5.09 7.57 2.48 o 4 3 7 3.19 3.65 2.45 o -4 4 7 2.01 3.97 2.65 o -3 4 7 1.81 7.98 3.35 o -2 4 7 1.10 3.00 2.14 o -1 4 7 63.07 50.97 6.28 o 0 4 7 0.36 0.53 1.65 o 1 4 7 62.97 58.33 6.73 o 2 4 7 1.10 4.87 2.19 o 3 4 7 1.84 4.19 2.70 o 4 4 7 2.00 5.52 3.02 o -4 5 7 9.95 8.83 10.07 o -3 5 7 14.21 9.85 6.09 o -2 5 7 6.27 0.03 3.00 o -1 5 7 18.67 2.95 1.84 o 0 5 7 12.89 6.90 1.75 o 1 5 7 18.59 2.45 2.45 o 2 5 7 6.27 8.97 8.76 o 0 0 8 343.70 334.73 12.73 o 1 0 8 4.66 4.02 1.37 o 2 0 8 216.36 179.82 5.79 o 3 0 8 2.98 1.34 4.99 o 4 0 8 19.84 12.23 3.88 o -4 1 8 3.02 2.09 2.75 o -3 1 8 7.48 7.43 3.78 o -2 1 8 50.85 54.25 3.66 o -1 1 8 103.44 106.97 7.27 o 0 1 8 32.93 29.39 4.09 o 1 1 8 103.53 115.06 8.20 o 2 1 8 50.75 56.03 3.97 o 3 1 8 7.49 6.86 4.72 o 4 1 8 2.99 2.11 2.48 o -4 2 8 3.65 4.47 2.71 o -3 2 8 4.83 14.15 3.57 o -2 2 8 13.13 7.73 2.91 o -1 2 8 19.40 15.38 3.47 o 0 2 8 1.02 8.83 2.89 o 1 2 8 19.39 16.19 3.24 o 2 2 8 13.12 8.70 2.73 o 3 2 8 4.81 6.57 2.79 o 4 2 8 3.65 4.02 2.67 o -4 3 8 14.89 8.52 2.94 o -3 3 8 5.44 5.78 3.23 o -2 3 8 5.48 11.81 2.90 o -1 3 8 8.92 9.34 2.26 o 0 3 8 16.30 13.92 2.37 o 1 3 8 8.99 7.95 2.51 o 2 3 8 5.50 12.49 2.91 o 3 3 8 5.44 6.30 3.12 o 4 3 8 14.91 15.01 3.44 o -3 4 8 3.38 5.46 2.99 o -2 4 8 13.16 19.28 5.03 o -1 4 8 4.09 6.50 2.72 o 0 4 8 6.91 8.74 3.04 o 1 4 8 4.13 5.51 2.48 o 2 4 8 13.13 11.79 3.33 o 3 4 8 3.43 6.30 3.10 o -3 5 8 6.35 10.24 9.03 o -2 5 8 15.48 11.40 4.91 o -1 5 8 29.95 14.76 3.34 o 0 5 8 6.52 5.37 2.24 o 1 5 8 30.01 22.55 4.48 o 2 5 8 15.52 12.35 5.32 o 3 5 8 6.33 3.83 5.30 o 2 0 9 0.03 0.00 5.93 o 3 0 9 1.23 5.44 4.26 o -3 1 9 5.92 5.52 3.00 o -2 1 9 0.52 3.22 3.28 o -1 1 9 64.76 66.03 5.73 o 0 1 9 24.00 22.24 3.47 o 1 1 9 64.77 67.88 6.79 o 2 1 9 0.51 3.85 3.94 o 3 1 9 5.91 3.75 3.21 o -3 2 9 24.19 20.58 5.56 o -2 2 9 2.71 9.19 2.84 o -1 2 9 9.94 11.07 3.00 o 0 2 9 0.02 5.42 1.95 o 1 2 9 9.91 5.72 2.53 o 2 2 9 2.73 10.42 4.01 o 3 2 9 24.15 16.92 4.31 o -3 3 9 12.15 13.93 4.34 o -2 3 9 11.32 12.92 3.39 o -1 3 9 0.20 1.25 2.61 o 0 3 9 33.40 34.41 6.64 o 1 3 9 0.19 0.80 2.28 o 2 3 9 11.34 9.42 3.03 o 3 3 9 12.14 12.20 4.27 o -3 4 9 11.18 4.99 3.23 o -2 4 9 0.57 3.94 2.95 o -1 4 9 29.06 22.62 4.70 o 0 4 9 1.33 6.68 3.59 o 1 4 9 29.07 19.90 3.16 o 2 4 9 0.57 2.96 2.49 o 3 4 9 11.17 6.83 3.53 o -2 5 9 5.84 2.38 3.74 o -1 5 9 27.78 19.66 5.53 o 0 5 9 0.68 4.22 3.27 o 1 5 9 27.81 19.66 6.27 o 2 5 9 5.83 3.14 4.94 o -3 1 10 9.83 9.31 4.85 o -2 1 10 11.05 10.43 3.39 o -1 1 10 21.20 14.61 3.98 o 0 1 10 26.61 34.89 4.44 o 1 1 10 21.19 20.90 4.46 o 2 1 10 11.05 7.98 3.86 o 3 1 10 9.85 9.77 3.99 o -3 2 10 3.35 4.62 4.01 o -2 2 10 3.20 5.32 3.02 o -1 2 10 4.06 5.54 2.46 o 0 2 10 0.10 2.78 3.81 o 1 2 10 4.07 6.41 2.69 o 2 2 10 3.21 2.70 3.93 o 3 2 10 3.35 5.60 4.23 o -2 3 10 9.78 7.79 3.66 o -1 3 10 8.76 6.02 2.60 o 0 3 10 0.68 6.56 3.86 o 1 3 10 8.70 10.80 3.41 o 2 3 10 9.77 8.08 4.64 o -2 4 10 1.66 4.73 4.43 o -1 4 10 4.48 4.98 3.08 o 0 4 10 0.33 5.93 3.07 o 1 4 10 4.50 5.23 2.55 o 2 4 10 1.66 6.76 3.41 o -2 5 10 4.86 3.39 3.09 o -1 5 10 6.74 1.07 3.45 o 0 5 10 51.52 34.31 7.26 o 1 5 10 6.71 2.12 4.88 o 2 5 10 4.87 11.77 8.26 o -2 1 11 8.66 12.57 8.87 o -1 1 11 3.22 5.70 7.68 o 0 1 11 0.93 8.71 5.04 o 1 1 11 3.23 3.76 4.01 o 2 1 11 8.68 13.34 6.20 o -2 2 11 0.96 0.35 4.50 o -1 2 11 0.88 0.00 3.49 o 0 2 11 8.52 7.53 3.10 o 1 2 11 0.87 0.05 2.59 o 2 2 11 0.95 0.38 3.43 o -1 3 11 9.69 9.19 4.01 o 0 3 11 22.87 17.09 4.01 o 1 3 11 9.70 13.34 3.68 o -1 4 11 11.92 7.47 3.29 o 0 4 11 0.08 8.75 3.71 o 1 4 11 11.92 10.66 4.20 o ################################################################## data_23butdiol_0.72GPa _database_code_depnum_ccdc_archive 'CCDC 870123' #TrackingRef '- All.cif' # CHEMICAL DATA _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,3-butanediol ; _chemical_name_common 2,3-butanediol _chemical_melting_point 298 _chemical_formula_moiety 'C4 H10 O2' _chemical_formula_sum 'C4 H10 O2' _chemical_formula_weight 90.12 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' # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _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 4.9973(10) _cell_length_b 9.4478(19) _cell_length_c 10.076(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 475.72(16) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2886 _cell_measurement_theta_min 4.31 _cell_measurement_theta_max 25.00 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 200 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.55 _exptl_absorpt_correction_T_max 0.90 _exptl_absorpt_process_details ; Correction for absorption of the diamond-anvil cell and the sample were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam Mickiewicz University Pozna\'n; Katrusiak, A. (2004) Z. Kristallogr. 219, 461-467). ; # EXPERIMENTAL DATA _exptl_special_details ; Data were collected at room temperature and pressure of 0.72(5) GPa (720000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line. ; _diffrn_ambient_temperature 295(2) _diffrn_ambient_environment 'diamond-anvil cell' _diffrn_ambient_pressure 720000 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KM-4 CCD' _diffrn_measurement_method '\f- and \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 1832 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0162 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 4.31 _diffrn_reflns_theta_max 25.00 _reflns_number_total 318 _reflns_number_gt 310 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisCCD (Oxford Diffraction, 2004)' _computing_cell_refinement 'CrysAlisRED (Oxford Diffraction, 2004)' _computing_data_reduction 'CrysAlisRED (Oxford Diffraction, 2004); REDSHABS (Katrusiak, A. 2003)' _computing_structure_solution 'SHELXS--97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL--97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1990)' _computing_publication_material 'SHELXL--97 (Sheldrick, 1997)' # REFINEMENT DATA _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. The DAC imposes severe restrictions on which reflections can be collected, resulting in a low data:parameter ratio. ; _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^)+(0.0525P)^2^+0.1868P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(3) _refine_ls_number_reflns 318 _refine_ls_number_parameters 55 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0375 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0935 _refine_ls_wR_factor_gt 0.0930 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 O1 O 0.3076(4) -0.05279(18) 0.1991(5) 0.045(2) Uani 1 1 d . . . H1 H 0.1626 -0.0933 0.1966 0.067 Uiso 1 1 calc R . . O2 O 0.1914(4) 0.31592(17) 0.2940(5) 0.041(2) Uani 1 1 d . . . H2 H 0.3432 0.3488 0.2960 0.049 Uiso 1 1 calc R . . C1 C 0.0668(7) 0.1246(4) 0.0674(9) 0.042(4) Uani 1 1 d . . . H11 H 0.0992 0.0607 -0.0050 0.063 Uiso 1 1 calc R . . H12 H 0.0859 0.2203 0.0370 0.063 Uiso 1 1 calc R . . H13 H -0.1113 0.1105 0.1005 0.063 Uiso 1 1 calc R . . C2 C 0.2687(5) 0.0961(3) 0.1783(8) 0.033(4) Uani 1 1 d . . . H21 H 0.4407 0.1350 0.1490 0.040 Uiso 1 1 calc R . . C3 C 0.2033(6) 0.1652(3) 0.3145(8) 0.031(3) Uani 1 1 d . . . H31 H 0.3491 0.1443 0.3765 0.037 Uiso 1 1 calc R . . C4 C -0.0573(6) 0.1204(3) 0.3765(8) 0.042(5) Uani 1 1 d . . . H41 H -0.1008 0.1834 0.4481 0.063 Uiso 1 1 calc R . . H42 H -0.0406 0.0256 0.4100 0.063 Uiso 1 1 calc R . . H43 H -0.1966 0.1235 0.3110 0.063 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 O1 0.0319(10) 0.0241(12) 0.078(7) -0.0003(15) -0.003(2) 0.0041(7) O2 0.0302(10) 0.0252(12) 0.067(8) -0.0044(13) -0.001(2) -0.0005(7) C1 0.0381(19) 0.043(2) 0.044(13) -0.001(3) -0.008(3) 0.0001(14) C2 0.0243(14) 0.0266(19) 0.049(13) 0.001(2) 0.018(3) 0.0006(10) C3 0.0257(12) 0.0258(18) 0.040(12) 0.002(2) -0.005(3) 0.0027(11) C4 0.0344(15) 0.040(2) 0.051(15) -0.003(2) 0.005(3) -0.0001(13) # MOLECULAR GEOMETRY _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 O1 C2 1.435(4) . ? O2 C3 1.440(3) . ? C1 C2 1.530(11) . ? C2 C3 1.555(11) . ? C3 C4 1.505(6) . ? 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 C2 C1 111.6(4) . . ? O1 C2 C3 108.1(6) . . ? C1 C2 C3 115.6(4) . . ? O2 C3 C4 107.6(3) . . ? O2 C3 C2 107.3(6) . . ? C4 C3 C2 115.5(4) . . ? _diffrn_measured_fraction_theta_max 0.374 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.374 _refine_diff_density_max 0.100 _refine_diff_density_min -0.085 _refine_diff_density_rms 0.024 # # h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag # loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_squared_calc _refln_F_squared_meas _refln_F_squared_sigma _refln_observed_status 2 0 0 1184.20 1090.14 9.77 o 4 0 0 58.49 67.89 0.75 o 2 1 0 240.44 232.54 2.05 o 3 1 0 135.33 157.52 1.06 o 4 1 0 154.22 158.72 1.60 o 5 1 0 3.63 3.08 0.27 o 0 2 0 3.02 5.57 0.12 o 2 2 0 0.11 0.08 0.02 o 3 2 0 12.50 10.69 0.17 o 4 2 0 1.19 0.22 0.09 o 5 2 0 2.84 1.51 0.28 o 1 3 0 209.42 183.49 1.36 o 2 3 0 0.10 0.11 0.03 o 3 3 0 4.81 8.90 0.13 o 4 3 0 2.92 3.49 0.21 o 5 3 0 9.56 10.63 0.34 o 1 4 0 111.82 114.08 0.68 o 2 4 0 0.86 0.54 0.06 o 3 4 0 112.31 110.94 1.78 o 4 4 0 14.08 12.75 0.34 o 5 4 0 14.15 12.43 0.42 o 1 5 0 345.23 394.51 1.54 o 2 5 0 6.99 4.47 0.12 o 3 5 0 56.03 58.66 0.64 o 4 5 0 0.43 0.17 0.13 o 5 5 0 1.60 1.17 0.26 o 1 6 0 65.30 64.06 0.41 o 2 6 0 8.32 10.85 0.29 o 3 6 0 28.57 29.89 0.53 o 4 6 0 3.93 3.96 0.31 o 5 6 0 9.24 10.35 0.84 o 2 7 0 168.86 157.88 1.83 o 3 7 0 6.17 6.69 0.62 o 1 0 1 590.30 596.93 1.32 o 2 0 1 73.34 66.44 0.52 o 3 0 1 0.02 0.19 0.04 o 4 0 1 237.99 224.41 2.41 o 5 0 1 0.35 0.23 0.15 o -5 1 1 10.02 8.60 0.36 o -4 1 1 64.08 59.70 0.66 o -3 1 1 139.21 146.31 1.08 o -2 1 1 408.03 440.35 1.02 o 2 1 1 408.19 446.88 1.90 o 3 1 1 139.31 143.62 1.40 o 4 1 1 64.08 58.93 1.08 o 5 1 1 10.04 8.07 0.35 o -5 2 1 116.80 128.28 2.00 o -4 2 1 22.29 24.00 0.28 o -3 2 1 419.11 422.33 4.04 o -2 2 1 108.34 101.96 1.19 o -1 2 1 304.46 301.79 2.86 o 0 2 1 466.97 451.37 4.18 o 1 2 1 304.07 303.01 3.42 o 2 2 1 108.35 101.04 1.15 o 3 2 1 419.69 407.78 4.14 o 4 2 1 22.30 23.61 0.49 o 5 2 1 116.52 127.40 4.28 o -5 3 1 8.52 8.18 0.44 o -4 3 1 4.18 3.73 0.18 o -3 3 1 5.35 6.38 0.19 o -2 3 1 3.98 4.19 0.08 o -1 3 1 185.36 169.01 1.60 o 0 3 1 15.37 14.08 0.16 o 1 3 1 185.44 168.48 1.84 o 2 3 1 4.00 4.21 0.08 o 3 3 1 5.41 5.82 0.13 o 4 3 1 4.20 3.36 0.20 o 5 3 1 8.56 7.50 0.39 o -5 4 1 4.29 3.87 0.38 o -4 4 1 44.31 42.91 0.44 o -3 4 1 2.45 2.15 0.14 o -2 4 1 53.95 58.50 0.84 o -1 4 1 149.52 142.62 1.48 o 0 4 1 2.21 3.87 0.09 o 1 4 1 149.26 144.73 2.13 o 2 4 1 53.94 60.47 0.80 o 3 4 1 2.42 2.17 0.13 o 4 4 1 44.30 41.76 0.68 o 5 4 1 4.27 3.12 0.33 o -5 5 1 6.50 5.05 0.50 o -4 5 1 4.31 4.42 0.35 o -3 5 1 59.57 52.50 0.46 o -2 5 1 6.70 6.18 0.15 o -1 5 1 657.69 700.26 8.10 o 0 5 1 1.17 2.91 0.11 o 1 5 1 657.89 698.68 10.48 o 2 5 1 6.64 6.23 0.24 o 3 5 1 59.61 52.25 1.01 o 4 5 1 4.30 4.38 0.40 o 5 5 1 6.50 4.10 0.70 o -5 6 1 80.28 91.89 4.35 o -4 6 1 5.60 5.19 0.43 o -3 6 1 150.54 160.06 2.36 o -2 6 1 79.55 74.52 0.43 o -1 6 1 58.48 64.18 0.90 o 0 6 1 887.67 904.24 11.51 o 1 6 1 58.41 65.68 1.25 o 2 6 1 79.60 75.32 1.26 o 3 6 1 150.69 155.76 2.80 o 4 6 1 5.59 4.54 0.73 o 5 6 1 80.15 90.36 1.15 o -4 7 1 44.41 42.77 0.83 o -3 7 1 0.98 0.35 0.17 o -2 7 1 66.14 62.85 0.65 o -1 7 1 8.08 5.27 0.23 o 0 7 1 107.36 112.11 1.20 o 1 7 1 8.07 5.28 0.23 o 2 7 1 66.09 60.11 0.88 o 3 7 1 0.99 0.54 0.18 o 4 7 1 44.38 42.40 1.36 o -4 8 1 2.73 2.71 0.92 o -3 8 1 14.04 16.37 0.81 o -2 8 1 48.53 47.82 2.28 o -1 8 1 30.89 27.64 0.61 o 0 8 1 30.45 25.43 0.42 o 1 8 1 30.91 29.64 1.55 o 2 8 1 48.47 50.47 0.90 o 3 8 1 14.05 15.99 0.74 o 4 8 1 2.76 1.85 0.75 o 3 0 2 86.18 85.43 1.40 o 4 0 2 41.89 40.46 0.71 o 5 0 2 68.61 68.50 0.84 o -5 1 2 23.69 22.25 0.50 o -4 1 2 130.41 137.01 2.37 o -3 1 2 142.48 144.93 2.57 o -2 1 2 311.20 320.63 3.49 o 2 1 2 310.83 309.39 8.68 o 3 1 2 142.39 147.49 3.30 o 4 1 2 130.36 135.03 1.74 o 5 1 2 23.67 22.19 0.56 o -5 2 2 1.68 1.23 0.36 o -4 2 2 41.37 41.62 0.52 o -3 2 2 57.12 60.11 0.77 o -2 2 2 202.58 222.36 2.93 o -1 2 2 851.80 840.12 14.41 o 1 2 2 851.24 807.63 22.84 o 2 2 2 202.56 215.91 6.14 o 3 2 2 57.19 57.24 1.25 o 4 2 2 41.38 38.88 0.40 o 5 2 2 1.67 1.10 0.26 o -5 3 2 2.96 3.16 0.79 o -4 3 2 6.28 4.98 0.80 o -3 3 2 35.21 36.06 0.38 o -2 3 2 12.84 14.17 0.18 o -1 3 2 238.17 244.79 4.60 o 0 3 2 11.65 12.68 0.14 o 1 3 2 238.39 241.34 5.94 o 2 3 2 12.83 14.17 0.34 o 3 3 2 35.08 34.57 0.55 o 4 3 2 6.27 4.32 0.44 o 5 3 2 2.95 2.40 1.00 o -5 4 2 55.27 58.74 1.16 o -4 4 2 8.92 8.96 0.52 o -3 4 2 114.62 110.76 1.60 o -2 4 2 75.94 71.73 1.04 o -1 4 2 61.54 62.92 1.11 o 0 4 2 19.83 16.80 0.31 o 1 4 2 61.70 63.67 1.24 o 2 4 2 75.90 70.71 0.77 o 3 4 2 114.30 108.71 1.12 o 4 4 2 8.91 8.73 0.59 o 5 4 2 55.57 52.39 1.06 o -5 5 2 24.89 25.65 1.05 o -4 5 2 12.80 12.17 0.50 o -3 5 2 100.22 106.95 1.14 o -2 5 2 26.53 29.52 0.34 o -1 5 2 159.99 175.00 1.52 o 0 5 2 13.33 11.81 0.15 o 1 5 2 160.02 171.34 2.35 o 2 5 2 26.60 28.84 0.44 o 3 5 2 100.13 102.65 1.10 o 4 5 2 12.83 10.76 0.52 o 5 5 2 24.88 23.06 2.16 o -4 6 2 91.00 105.18 1.65 o -3 6 2 49.08 50.39 0.44 o -2 6 2 5.59 5.12 0.20 o -1 6 2 290.52 277.09 3.87 o 0 6 2 31.12 35.54 0.34 o 1 6 2 290.55 277.42 4.08 o 2 6 2 5.63 5.20 0.19 o 3 6 2 49.13 48.47 1.04 o 4 6 2 90.98 97.61 3.51 o -4 7 2 62.50 66.72 2.04 o -3 7 2 4.08 2.94 0.30 o -2 7 2 160.67 167.34 1.56 o -1 7 2 12.50 13.51 0.26 o 0 7 2 102.89 111.15 1.49 o 1 7 2 12.50 13.26 0.27 o 2 7 2 160.73 158.66 2.48 o 3 7 2 4.07 2.88 0.36 o 4 7 2 62.57 62.64 2.36 o -3 8 2 25.50 27.63 0.76 o -2 8 2 40.16 42.80 1.35 o -1 8 2 22.35 25.81 0.55 o 0 8 2 206.09 202.38 2.21 o 1 8 2 22.34 25.65 0.59 o 2 8 2 40.11 40.19 0.54 o 3 8 2 25.52 26.87 0.90 o -3 9 2 7.56 7.45 0.72 o -2 9 2 6.82 5.93 0.51 o -1 9 2 11.84 9.63 0.43 o 0 9 2 0.60 0.47 0.18 o 1 9 2 11.82 8.91 0.34 o 2 9 2 6.88 6.89 0.52 o 3 9 2 7.58 7.78 0.74 o -2 10 2 5.58 6.55 1.03 o -1 10 2 0.87 0.68 0.74 o 0 10 2 1.50 0.96 0.71 o 1 10 2 0.89 0.25 0.43 o 2 10 2 5.60 5.97 0.97 o -4 1 3 27.17 22.66 0.98 o -5 2 3 37.78 43.10 1.45 o -4 2 3 0.99 1.51 0.40 o -3 2 3 67.36 77.07 2.00 o 3 2 3 67.31 73.74 3.37 o 4 2 3 0.99 1.83 0.53 o 5 2 3 37.67 39.04 1.51 o -5 3 3 2.14 2.59 0.74 o -4 3 3 16.22 15.28 0.69 o -3 3 3 34.37 34.66 0.60 o -2 3 3 37.47 37.43 1.98 o 2 3 3 37.57 39.13 0.54 o 3 3 3 34.36 34.57 0.74 o 4 3 3 16.27 15.39 0.67 o 5 3 3 2.16 2.72 0.52 o -5 4 3 19.07 21.70 2.20 o -4 4 3 12.46 11.07 0.68 o -3 4 3 22.41 25.96 0.97 o -2 4 3 0.82 0.21 0.10 o -1 4 3 170.52 164.87 0.68 o 0 4 3 0.34 0.76 0.21 o 1 4 3 171.14 156.00 1.05 o 2 4 3 0.82 0.29 0.14 o 3 4 3 22.29 25.15 1.11 o 4 4 3 12.45 9.95 0.63 o 5 4 3 19.08 21.13 0.90 o -5 5 3 4.66 5.30 0.93 o -4 5 3 3.56 3.37 0.57 o -3 5 3 34.58 35.50 0.82 o -2 5 3 4.41 3.70 0.19 o -1 5 3 179.35 176.05 1.93 o 0 5 3 32.01 33.28 0.31 o 1 5 3 179.20 173.36 2.10 o 2 5 3 4.37 3.61 0.20 o 3 5 3 34.65 34.76 0.54 o 4 5 3 3.54 2.99 0.47 o 5 5 3 4.65 4.11 0.58 o -4 6 3 7.25 4.81 1.38 o -3 6 3 32.49 26.61 0.54 o -2 6 3 136.40 136.18 1.01 o -1 6 3 55.27 54.17 0.88 o 0 6 3 0.21 0.40 0.11 o 1 6 3 55.23 53.60 1.18 o 2 6 3 136.40 129.84 1.13 o 3 6 3 32.49 26.23 0.67 o 4 6 3 7.25 4.64 0.56 o -4 7 3 27.14 27.85 1.41 o -3 7 3 1.30 0.73 0.25 o -2 7 3 231.26 253.54 3.36 o -1 7 3 13.01 13.76 0.38 o 0 7 3 254.75 263.63 3.97 o 1 7 3 12.98 13.60 0.30 o 2 7 3 231.19 248.59 3.90 o 3 7 3 1.30 1.14 0.29 o 4 7 3 27.09 27.07 1.11 o -3 8 3 26.76 25.58 0.66 o -2 8 3 49.81 58.66 0.76 o -1 8 3 123.40 121.99 1.04 o 0 8 3 2.78 1.51 0.23 o 1 8 3 123.36 121.61 1.89 o 2 8 3 49.79 53.99 1.75 o 3 8 3 26.78 25.60 0.57 o -3 9 3 13.17 13.42 0.66 o -2 9 3 2.83 2.61 0.33 o -1 9 3 14.95 14.24 0.39 o 0 9 3 4.89 3.12 0.31 o 1 9 3 14.98 14.11 0.38 o 2 9 3 2.81 2.87 0.33 o 3 9 3 13.15 12.44 0.68 o -2 10 3 15.68 16.93 0.68 o -1 10 3 0.13 0.30 0.18 o 0 10 3 4.11 2.78 0.30 o 1 10 3 0.13 0.45 0.20 o 2 10 3 15.67 15.82 0.86 o -3 5 4 91.12 90.92 1.60 o 3 5 4 91.28 84.48 1.44 o -4 6 4 16.98 13.70 1.16 o -3 6 4 78.67 76.52 1.12 o -2 6 4 105.35 107.72 2.21 o -1 6 4 382.16 407.72 3.19 o 1 6 4 382.00 395.05 1.34 o 2 6 4 105.35 99.09 2.48 o 3 6 4 78.70 76.08 2.05 o 4 6 4 17.02 17.25 1.15 o -4 7 4 19.24 18.43 1.40 o -3 7 4 4.66 4.73 0.72 o -2 7 4 40.48 40.54 1.09 o -1 7 4 4.80 4.30 0.40 o 0 7 4 186.84 194.33 2.20 o 1 7 4 4.81 4.29 0.35 o 2 7 4 40.56 38.07 0.71 o 3 7 4 4.66 5.13 0.46 o 4 7 4 19.26 17.65 1.44 o -3 8 4 11.89 9.24 0.65 o -2 8 4 1.01 0.73 0.28 o -1 8 4 2.92 2.23 0.37 o 0 8 4 66.30 77.04 1.70 o 1 8 4 2.92 2.61 0.34 o 2 8 4 1.03 0.90 0.31 o 3 8 4 11.89 11.02 0.83 o -2 9 4 2.37 2.35 0.47 o -1 9 4 0.32 0.20 0.15 o 0 9 4 7.17 7.13 0.37 o 1 9 4 0.33 0.36 0.21 o 2 9 4 2.37 2.42 0.40 o -1 10 4 2.62 2.89 0.40 o 0 10 4 2.65 2.81 0.43 o 1 10 4 2.68 2.97 0.43 o ################################################################## data_23butdiol_0.97GPa _database_code_depnum_ccdc_archive 'CCDC 870124' #TrackingRef '- All.cif' # CHEMICAL DATA _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,3-butanediol ; _chemical_name_common 2,3-butanediol _chemical_melting_point 298 _chemical_formula_moiety 'C4 H10 O2' _chemical_formula_sum 'C4 H10 O2' _chemical_formula_weight 90.12 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' # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _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 4.9467(10) _cell_length_b 9.3791(19) _cell_length_c 9.834(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 456.25(16) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2301 _cell_measurement_theta_min 4.35 _cell_measurement_theta_max 28.12 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 200 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.54 _exptl_absorpt_correction_T_max 0.93 _exptl_absorpt_process_details ; Correction for absorption of the diamond-anvil cell and the sample were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam Mickiewicz University Pozna\'n; Katrusiak, A. (2004) Z. Kristallogr. 219, 461-467). ; # EXPERIMENTAL DATA _exptl_special_details ; Data were collected at room temperature and pressure of 0.97(5) GPa (970000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line. ; _diffrn_ambient_temperature 295(2) _diffrn_ambient_environment 'diamond-anvil cell' _diffrn_ambient_pressure 970000 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KM-4 CCD' _diffrn_measurement_method '\f- and \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 1954 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -3 _diffrn_reflns_limit_l_max 3 _diffrn_reflns_theta_min 4.35 _diffrn_reflns_theta_max 28.12 _reflns_number_total 284 _reflns_number_gt 268 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisCCD (Oxford Diffraction, 2004)' _computing_cell_refinement 'CrysAlisRED (Oxford Diffraction, 2004)' _computing_data_reduction 'CrysAlisRED (Oxford Diffraction, 2004); REDSHABS (Katrusiak, A. 2003)' _computing_structure_solution 'SHELXS--97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL--97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1990)' _computing_publication_material 'SHELXL--97 (Sheldrick, 1997)' # REFINEMENT DATA _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. The DAC imposes severe restrictions on which reflections can be collected, resulting in a low data:parameter ratio. ; _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^)+(0.0437P)^2^+0.3168P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 3(4) _refine_ls_number_reflns 284 _refine_ls_number_parameters 25 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1045 _refine_ls_wR_factor_gt 0.1021 _refine_ls_goodness_of_fit_ref 1.126 _refine_ls_restrained_S_all 1.126 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 O1 O 0.3111(4) -0.0548(2) 0.1948(8) 0.0241(7) Uiso 1 1 d . . . H1 H 0.1650 -0.0960 0.1923 0.036 Uiso 1 1 calc R . . O2 O 0.1896(5) 0.3167(2) 0.2944(7) 0.0241(7) Uiso 1 1 d . . . H2 H 0.3430 0.3497 0.2965 0.029 Uiso 1 1 calc R . . C1 C 0.0641(8) 0.1241(4) 0.0631(13) 0.0327(11) Uiso 1 1 d . . . H11 H 0.0951 0.0597 -0.0112 0.049 Uiso 1 1 calc R . . H12 H 0.0826 0.2205 0.0318 0.049 Uiso 1 1 calc R . . H13 H -0.1150 0.1099 0.0982 0.049 Uiso 1 1 calc R . . C2 C 0.2701(6) 0.0956(3) 0.1751(11) 0.0213(8) Uiso 1 1 d . . . H21 H 0.4427 0.1359 0.1450 0.026 Uiso 1 1 calc R . . C3 C 0.2014(7) 0.1645(3) 0.3149(11) 0.0214(8) Uiso 1 1 d . . . H31 H 0.3475 0.1431 0.3790 0.026 Uiso 1 1 calc R . . C4 C -0.0650(7) 0.1188(4) 0.3774(12) 0.0306(10) Uiso 1 1 d . . . H41 H -0.1110 0.1823 0.4503 0.046 Uiso 1 1 calc R . . H42 H -0.0485 0.0234 0.4119 0.046 Uiso 1 1 calc R . . H43 H -0.2042 0.1216 0.3094 0.046 Uiso 1 1 calc R . . # MOLECULAR GEOMETRY _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 O1 C2 1.438(4) . ? O2 C3 1.442(4) . ? C1 C2 1.524(14) . ? C2 C3 1.556(13) . ? C3 C4 1.516(8) . ? 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 C2 C1 111.3(5) . . ? O1 C2 C3 108.7(7) . . ? C1 C2 C3 114.8(4) . . ? O2 C3 C4 107.5(3) . . ? O2 C3 C2 107.3(7) . . ? C4 C3 C2 115.4(5) . . ? _diffrn_measured_fraction_theta_max 0.265 _diffrn_reflns_theta_full 28.12 _diffrn_measured_fraction_theta_full 0.265 _refine_diff_density_max 0.094 _refine_diff_density_min -0.097 _refine_diff_density_rms 0.028 # # h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag # loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_squared_calc _refln_F_squared_meas _refln_F_squared_sigma _refln_observed_status 2 0 0 1198.86 1148.73 14.99 o 4 0 0 31.00 39.27 0.69 o 1 1 0 1429.39 1337.57 5.80 o 2 1 0 244.64 246.61 4.26 o 3 1 0 134.27 134.52 0.90 o 4 1 0 169.88 181.11 1.27 o 5 1 0 2.86 2.88 0.36 o 6 1 0 25.96 25.86 1.28 o 0 2 0 5.71 6.64 0.13 o 1 2 0 1242.44 1158.79 11.15 o 2 2 0 0.23 0.11 0.03 o 3 2 0 6.20 6.11 0.19 o 4 2 0 1.21 0.52 0.17 o 5 2 0 5.78 3.79 0.40 o 6 2 0 1.19 1.09 0.50 o 1 3 0 206.17 180.46 1.14 o 2 3 0 0.43 0.28 0.06 o 3 3 0 4.11 7.31 0.26 o 4 3 0 4.11 4.08 0.28 o 5 3 0 15.11 14.65 0.56 o 6 3 0 0.51 1.06 0.60 o 0 4 0 2089.00 2176.63 36.73 o 1 4 0 133.72 144.44 1.54 o 2 4 0 0.03 0.35 0.08 o 3 4 0 122.97 128.30 1.14 o 4 4 0 9.75 10.09 0.44 o 5 4 0 15.20 11.66 0.84 o 6 4 0 19.70 24.00 1.53 o 1 5 0 366.55 367.66 5.21 o 2 5 0 8.68 6.22 0.16 o 3 5 0 59.43 67.12 0.75 o 4 5 0 0.50 0.72 0.34 o 5 5 0 1.04 1.11 0.44 o 0 6 0 14.56 16.15 0.54 o 1 6 0 73.25 74.90 1.05 o 2 6 0 8.34 8.63 0.28 o 3 6 0 28.26 28.25 0.52 o 4 6 0 3.00 3.91 0.56 o 5 6 0 13.91 15.19 0.98 o 1 7 0 21.61 16.52 0.61 o 2 7 0 189.36 186.96 3.20 o 3 7 0 5.55 8.65 0.60 o 4 7 0 145.68 155.91 3.00 o 0 8 0 45.32 54.18 1.01 o 1 8 0 1.10 1.23 0.28 o 2 8 0 238.35 240.91 2.50 o 3 8 0 34.76 39.00 1.73 o 1 0 1 537.63 561.71 7.71 o 2 0 1 67.17 56.65 0.59 o 3 0 1 1.01 0.57 0.13 o 4 0 1 291.59 271.37 1.54 o 5 0 1 0.05 0.82 0.35 o 6 0 1 2.33 1.12 0.41 o -6 1 1 22.80 21.46 1.10 o -5 1 1 10.23 6.15 0.63 o -4 1 1 72.56 64.58 0.85 o -3 1 1 150.35 150.35 1.73 o -2 1 1 486.28 523.37 5.84 o -1 1 1 1235.31 1265.42 10.49 o 1 1 1 1235.44 1188.11 16.41 o 2 1 1 486.50 521.65 8.05 o 3 1 1 150.44 143.23 3.30 o 4 1 1 72.51 64.89 0.70 o 5 1 1 10.26 7.44 0.83 o 6 1 1 22.77 20.49 1.08 o -6 2 1 42.81 47.72 2.14 o -5 2 1 138.07 153.45 1.53 o -4 2 1 25.31 26.10 0.53 o -3 2 1 465.48 460.99 4.34 o -2 2 1 96.00 93.53 1.13 o -1 2 1 315.34 317.79 3.83 o 0 2 1 405.93 394.03 5.07 o 1 2 1 314.92 325.02 6.71 o 2 2 1 96.01 93.11 1.29 o 3 2 1 466.13 464.24 3.91 o 4 2 1 25.32 25.88 0.54 o 5 2 1 137.74 151.19 1.95 o 6 2 1 42.83 41.72 2.83 o -6 3 1 3.43 0.87 1.16 o -5 3 1 16.06 11.68 0.66 o -4 3 1 6.16 5.27 0.37 o -3 3 1 7.34 8.18 0.30 o -2 3 1 3.51 3.32 0.13 o -1 3 1 201.58 182.14 2.65 o 0 3 1 9.93 12.32 0.28 o 1 3 1 201.68 190.79 3.57 o 2 3 1 3.53 3.24 0.15 o 3 3 1 7.41 7.67 0.31 o 4 3 1 6.20 5.08 0.39 o 5 3 1 16.12 12.17 0.65 o 6 3 1 3.45 3.97 1.98 o -5 4 1 5.83 6.85 1.94 o -4 4 1 58.14 57.96 1.10 o -3 4 1 3.44 2.53 0.21 o -2 4 1 54.28 62.75 1.33 o -1 4 1 140.89 129.83 3.57 o 0 4 1 0.86 1.97 0.25 o 1 4 1 140.62 135.84 1.71 o 2 4 1 54.27 61.25 1.17 o 3 4 1 3.42 7.07 1.67 o 4 4 1 58.14 57.20 0.79 o 5 4 1 5.81 5.01 0.79 o -5 5 1 10.02 7.35 0.83 o -4 5 1 3.36 3.63 0.52 o -3 5 1 57.54 47.58 0.85 o -2 5 1 7.23 5.68 0.24 o -1 5 1 660.23 715.64 6.50 o 0 5 1 1.24 2.62 0.19 o 1 5 1 660.46 705.90 8.66 o 2 5 1 7.17 5.48 0.23 o 3 5 1 57.58 46.98 0.82 o 4 5 1 3.36 2.94 0.45 o 5 5 1 10.02 8.58 0.93 o -5 6 1 104.11 113.08 4.47 o -4 6 1 3.10 1.84 0.39 o -3 6 1 192.31 212.68 1.92 o -2 6 1 74.19 77.63 1.01 o -1 6 1 69.05 79.91 1.12 o 0 6 1 869.30 927.76 9.45 o 1 6 1 68.97 75.97 1.89 o 2 6 1 74.23 76.53 1.31 o 3 6 1 192.52 208.73 4.33 o 4 6 1 3.10 2.23 0.46 o 5 6 1 103.94 117.63 2.27 o -5 7 1 2.46 1.84 1.36 o -4 7 1 57.25 50.75 1.59 o -3 7 1 2.25 1.09 0.29 o -2 7 1 74.71 71.86 1.16 o -1 7 1 15.46 11.03 0.45 o 0 7 1 114.84 120.42 5.02 o 1 7 1 15.44 11.17 0.61 o 2 7 1 74.65 71.87 1.25 o 3 7 1 2.26 0.83 0.38 o 4 7 1 57.20 52.16 1.52 o 5 7 1 2.47 0.89 1.18 o -5 8 1 7.22 6.15 1.69 o -4 8 1 4.25 2.06 0.96 o -3 8 1 12.08 12.41 0.85 o -2 8 1 60.93 64.54 0.93 o -1 8 1 35.96 34.06 0.69 o 0 8 1 28.99 23.87 0.57 o 1 8 1 35.97 33.79 0.68 o 2 8 1 60.87 63.53 1.27 o 3 8 1 12.08 11.74 0.87 o 4 8 1 4.29 2.09 1.44 o -4 9 1 7.90 5.85 1.96 o -3 9 1 15.46 14.00 2.42 o -2 9 1 5.60 5.66 0.68 o -1 9 1 47.22 46.40 0.78 o 0 9 1 0.20 0.52 0.28 o 1 9 1 47.20 47.75 1.76 o 2 9 1 5.53 5.26 0.69 o 3 9 1 15.46 15.89 1.67 o 4 9 1 7.85 11.73 2.14 o -3 10 1 17.06 12.92 1.52 o -2 10 1 3.78 1.85 0.95 o -1 10 1 10.70 9.18 0.89 o 0 10 1 29.50 37.30 1.04 o 1 10 1 10.74 8.72 0.97 o 2 10 1 3.82 1.34 1.30 o 3 0 2 90.80 85.52 1.86 o 4 0 2 29.41 32.96 0.72 o -5 1 2 23.80 20.16 2.17 o -4 1 2 167.41 165.47 1.88 o -3 1 2 147.52 147.95 4.17 o 3 1 2 147.44 154.45 3.58 o 4 1 2 167.33 171.10 2.16 o 5 1 2 23.78 20.45 1.88 o -5 2 2 3.11 3.70 1.52 o -4 2 2 42.57 47.64 1.87 o -3 2 2 60.20 56.98 1.29 o -2 2 2 228.69 252.49 1.15 o 2 2 2 228.68 240.56 1.57 o 3 2 2 60.28 50.38 1.83 o 4 2 2 42.58 41.82 2.66 o 5 2 2 3.09 1.37 1.70 o -5 3 2 4.59 5.40 2.14 o -4 3 2 10.72 8.08 0.80 o -3 3 2 33.63 36.60 0.78 o -2 3 2 13.19 15.48 1.02 o -1 3 2 232.63 248.57 8.07 o 1 3 2 232.89 249.43 3.92 o 2 3 2 13.15 16.83 1.11 o 3 3 2 33.50 37.19 1.08 o 4 3 2 10.71 8.02 0.84 o 5 3 2 4.58 4.92 1.12 o -5 4 2 60.83 70.01 2.38 o -4 4 2 7.92 9.06 1.26 o -3 4 2 143.70 132.80 1.71 o -2 4 2 97.96 87.79 1.77 o -1 4 2 72.62 76.55 0.94 o 0 4 2 22.85 18.00 0.64 o 1 4 2 72.82 74.84 1.16 o 2 4 2 97.89 89.59 1.06 o 3 4 2 143.30 133.91 1.82 o 4 4 2 7.91 8.96 1.07 o 5 4 2 61.18 68.40 2.38 o -5 5 2 30.70 22.75 1.72 o -4 5 2 16.33 21.91 1.57 o -3 5 2 125.33 131.25 1.16 o -2 5 2 29.36 34.34 1.32 o -1 5 2 178.43 189.57 3.41 o 0 5 2 19.29 14.65 0.40 o 1 5 2 178.46 191.86 4.27 o 2 5 2 29.44 34.13 0.63 o 3 5 2 125.20 127.05 1.19 o 4 5 2 16.37 19.85 1.32 o 5 5 2 30.67 23.05 2.11 o -5 6 2 2.26 3.38 1.33 o -4 6 2 114.91 130.02 4.19 o -3 6 2 50.52 52.63 1.27 o -2 6 2 5.09 3.93 0.35 o -1 6 2 362.57 339.59 5.74 o 0 6 2 28.54 35.63 0.65 o 1 6 2 362.58 344.40 4.59 o 2 6 2 5.13 3.95 0.40 o 3 6 2 50.58 51.55 0.87 o 4 6 2 114.87 121.21 2.89 o 5 6 2 2.27 2.70 0.80 o -5 7 2 2.14 1.93 1.49 o -4 7 2 63.20 66.56 3.01 o -3 7 2 3.01 1.50 0.43 o -2 7 2 183.98 186.89 1.82 o -1 7 2 15.55 17.51 0.55 o 0 7 2 121.81 134.02 1.60 o 1 7 2 15.56 18.44 0.56 o 2 7 2 184.06 189.06 2.22 o 3 7 2 3.00 2.76 0.45 o 4 7 2 63.27 57.66 8.43 o 5 7 2 2.15 1.45 1.36 o -4 8 2 2.65 2.90 0.73 o -3 8 2 30.41 33.33 1.06 o -2 8 2 34.04 41.82 0.82 o -1 8 2 21.04 21.98 0.75 o 0 8 2 233.65 244.70 3.39 o 1 8 2 21.04 22.96 0.97 o 2 8 2 33.99 41.12 1.26 o 3 8 2 30.42 33.85 1.09 o 4 8 2 2.64 2.94 0.85 o -4 9 2 4.07 2.34 1.40 o -3 9 2 7.20 4.62 0.59 o -2 9 2 10.80 8.80 0.82 o -1 9 2 12.26 11.90 0.57 o 0 9 2 1.84 0.98 0.38 o 1 9 2 12.25 12.59 0.62 o 2 9 2 10.89 8.37 0.76 o 3 9 2 7.22 7.36 0.85 o 4 9 2 4.11 4.43 1.60 o -3 10 2 2.18 1.94 0.77 o -2 10 2 7.31 5.26 0.66 o -1 10 2 4.89 4.63 0.51 o 0 10 2 1.34 1.59 0.41 o 1 10 2 4.93 4.39 0.39 o 2 10 2 7.34 5.99 0.76 o 3 10 2 2.16 1.45 0.62 o -2 11 2 12.35 15.75 1.36 o -1 11 2 5.40 5.19 0.70 o 0 11 2 2.28 1.94 0.73 o 1 11 2 5.36 4.23 0.55 o 2 11 2 12.36 15.88 2.62 o -1 12 2 16.06 15.00 2.39 o -3 6 3 36.58 27.78 2.15 o -2 6 3 136.52 131.66 3.00 o 2 6 3 136.53 120.10 7.09 o 3 6 3 36.59 34.97 2.13 o -3 7 3 5.24 4.97 2.66 o -2 7 3 279.16 275.55 15.34 o -1 7 3 16.60 14.15 1.06 o 0 7 3 261.81 264.91 5.52 o 1 7 3 16.56 15.58 0.79 o 2 7 3 279.08 269.63 6.87 o 3 7 3 5.24 5.54 2.50 o -2 8 3 70.57 67.45 3.87 o -1 8 3 141.92 130.74 3.61 o 0 8 3 0.55 0.64 0.53 o 1 8 3 141.89 126.19 3.20 o 2 8 3 70.55 66.52 3.37 o -2 9 3 4.82 3.56 0.93 o -1 9 3 14.83 13.76 2.49 o 0 9 3 6.53 7.36 1.37 o 1 9 3 14.87 10.57 1.17 o 2 9 3 4.78 2.70 0.72 o -1 10 3 0.20 0.99 0.72 o 1 10 3 0.21 0.77 0.68 o ################################################################## data_2but_2.14GPa _database_code_depnum_ccdc_archive 'CCDC 870125' #TrackingRef '- All.cif' # CHEMICAL DATA _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-butanol ; _chemical_name_common 2-butanol _chemical_melting_point 158 _chemical_formula_moiety 'C4 H10 O' _chemical_formula_sum 'C4 H10 O' _chemical_formula_weight 74.12 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' # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _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 5.0580(10) _cell_length_b 5.2221(10) _cell_length_c 16.054(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 424.04(14) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3268 _cell_measurement_theta_min 4.10 _cell_measurement_theta_max 24.94 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.161 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 168 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.36 _exptl_absorpt_correction_T_max 0.84 _exptl_absorpt_process_details ; Correction for absorption of the diamond-anvil cell and the sample were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam Mickiewicz University Pozna\'n; Katrusiak, A. (2004) Z. Kristallogr. 219, 461-467). ; # EXPERIMENTAL DATA _exptl_special_details ; Data were collected at room temperature and pressure of 2.14(5) GPa (2140000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line. ; _diffrn_ambient_temperature 295(2) _diffrn_ambient_environment 'diamond-anvil cell' _diffrn_ambient_pressure 2140000 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KM-4 CCD' _diffrn_measurement_method '\f- and \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3268 _diffrn_reflns_av_R_equivalents 0.1303 _diffrn_reflns_av_sigmaI/netI 0.0944 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.10 _diffrn_reflns_theta_max 24.94 _reflns_number_total 565 _reflns_number_gt 320 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisCCD (Oxford Diffraction, 2004)' _computing_cell_refinement 'CrysAlisRED (Oxford Diffraction, 2004)' _computing_data_reduction 'CrysAlisRED (Oxford Diffraction, 2004); REDSHABS (Katrusiak, A. 2003)' _computing_structure_solution 'SHELXS--97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL--97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1990)' _computing_publication_material 'SHELXL--97 (Sheldrick, 1997)' # REFINEMENT DATA _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. The DAC imposes severe restrictions on which reflections can be collected, resulting in a low data:parameter ratio. The relatively high R factors are due to the low quality of the crystal sample. Generally it was difficult to grow single crystals of this substance, and despite multiple tries the quality of the single crystal could not be improved. ; _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^)+(0.1091P)^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 constr _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 2(9) _refine_ls_number_reflns 565 _refine_ls_number_parameters 46 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.1265 _refine_ls_R_factor_gt 0.0805 _refine_ls_wR_factor_ref 0.2255 _refine_ls_wR_factor_gt 0.2045 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.247 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 O1 O 0.0740(11) 0.3512(7) 0.7733(3) 0.0748(18) Uani 1 1 d U . . H1 H 0.0252 0.4930 0.7576 0.112 Uiso 1 1 calc R . . C1 C -0.1157(19) 0.6174(10) 0.9240(5) 0.083(3) Uani 1 1 d U . . H11 H -0.2057 0.6184 0.9767 0.124 Uiso 1 1 calc R . . H12 H -0.2424 0.5980 0.8800 0.124 Uiso 1 1 calc R . . H13 H -0.0220 0.7758 0.9170 0.124 Uiso 1 1 calc R . . C2 C 0.0859(18) 0.3877(11) 0.9215(5) 0.073(2) Uani 1 1 d U . . H21 H 0.2119 0.4064 0.9667 0.087 Uiso 1 1 calc R . . H22 H -0.0089 0.2283 0.9299 0.087 Uiso 1 1 calc R . . C3 C 0.2249(16) 0.3769(9) 0.8443(5) 0.0542(19) Uani 1 1 d U . . H31 H 0.3269 0.5357 0.8390 0.065 Uiso 1 1 calc R . . C4 C 0.4239(15) 0.1515(10) 0.8452(4) 0.057(2) Uani 1 1 d U . . H41 H 0.5167 0.1460 0.7930 0.086 Uiso 1 1 calc R . . H42 H 0.3302 -0.0064 0.8532 0.086 Uiso 1 1 calc R . . H43 H 0.5480 0.1752 0.8897 0.086 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 O1 0.104(4) 0.042(2) 0.078(3) 0.000(2) -0.023(2) 0.006(3) C1 0.108(9) 0.035(3) 0.105(7) -0.003(3) 0.009(4) 0.005(4) C2 0.081(5) 0.054(3) 0.083(4) 0.011(3) -0.011(3) 0.002(3) C3 0.069(4) 0.021(2) 0.073(4) 0.007(3) -0.003(3) -0.006(3) C4 0.060(6) 0.038(3) 0.074(5) 0.004(3) 0.017(3) 0.019(4) # MOLECULAR GEOMETRY _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 O1 C3 1.378(8) . ? O1 H1 0.8200 . ? C1 C2 1.575(10) . ? C1 H11 0.9600 . ? C1 H12 0.9600 . ? C1 H13 0.9600 . ? C2 C3 1.426(11) . ? C2 H21 0.9700 . ? C2 H22 0.9700 . ? C3 C4 1.549(8) . ? C3 H31 0.9800 . ? C4 H41 0.9600 . ? C4 H42 0.9600 . ? C4 H43 0.9600 . ? 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 C3 O1 H1 109.5 . . ? C2 C1 H11 109.5 . . ? C2 C1 H12 109.5 . . ? H11 C1 H12 109.5 . . ? C2 C1 H13 109.5 . . ? H11 C1 H13 109.5 . . ? H12 C1 H13 109.5 . . ? C3 C2 C1 111.8(5) . . ? C3 C2 H21 109.3 . . ? C1 C2 H21 109.3 . . ? C3 C2 H22 109.3 . . ? C1 C2 H22 109.3 . . ? H21 C2 H22 107.9 . . ? O1 C3 C2 116.7(8) . . ? O1 C3 C4 107.0(5) . . ? C2 C3 C4 110.1(5) . . ? O1 C3 H31 107.6 . . ? C2 C3 H31 107.6 . . ? C4 C3 H31 107.6 . . ? C3 C4 H41 109.5 . . ? C3 C4 H42 109.5 . . ? H41 C4 H42 109.5 . . ? C3 C4 H43 109.5 . . ? H41 C4 H43 109.5 . . ? H42 C4 H43 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 C1 C2 C3 O1 -58.7(8) . . . . ? C1 C2 C3 C4 179.1(6) . . . . ? _diffrn_measured_fraction_theta_max 0.756 _diffrn_reflns_theta_full 24.94 _diffrn_measured_fraction_theta_full 0.756 _refine_diff_density_max 0.242 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.047 # # h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag # loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_squared_calc _refln_F_squared_meas _refln_F_squared_sigma _refln_observed_status 1 1 0 129.39 125.69 1.61 o 0 2 0 24.23 25.14 1.30 o 1 2 0 910.90 1001.70 3.77 o 2 2 0 55.13 55.05 3.90 o 1 3 0 36.13 33.69 1.53 o 2 3 0 106.22 110.42 3.31 o 3 3 0 4.49 5.03 2.42 o 0 4 0 673.15 788.66 6.64 o 1 4 0 34.75 31.61 3.12 o 2 4 0 0.61 0.96 1.68 o 3 4 0 3.63 5.29 2.69 o 1 5 0 5.82 8.76 3.48 o 2 5 0 5.98 3.90 2.10 o 3 5 0 2.10 5.07 3.06 o 1 6 0 4.96 11.42 4.10 o -2 1 1 200.97 164.81 9.15 o -1 1 1 1553.27 1589.65 12.32 o 0 1 1 416.18 428.02 1.98 o 1 1 1 1553.70 1562.57 13.96 o -3 2 1 2.47 1.69 3.23 o -2 2 1 8.59 6.02 2.24 o -1 2 1 370.73 411.23 15.88 o 0 2 1 260.50 297.78 1.83 o 1 2 1 370.50 418.02 10.56 o 2 2 1 8.58 5.49 2.03 o 3 2 1 2.46 1.16 3.65 o -3 3 1 5.33 2.46 1.00 o -2 3 1 91.28 87.07 3.21 o -1 3 1 248.58 271.52 3.81 o 0 3 1 20.62 23.63 1.35 o 1 3 1 248.55 273.23 2.97 o 2 3 1 91.26 86.91 2.44 o 3 3 1 5.34 5.21 1.54 o -4 4 1 0.58 1.14 5.02 o -3 4 1 5.05 3.62 2.59 o -2 4 1 0.94 0.82 1.82 o -1 4 1 36.92 39.42 3.36 o 0 4 1 1.50 4.62 2.12 o 1 4 1 36.87 39.92 3.48 o 2 4 1 0.95 0.76 1.24 o 3 4 1 5.05 4.98 2.50 o -3 5 1 12.30 7.96 3.63 o -2 5 1 1.43 6.86 1.99 o -1 5 1 54.56 72.64 5.58 o 0 5 1 12.61 19.19 1.66 o 1 5 1 54.60 70.74 7.11 o 2 5 1 1.43 5.39 2.01 o 3 5 1 12.27 8.96 3.09 o -1 6 1 11.58 19.25 3.01 o 0 6 1 10.39 21.94 5.71 o 1 6 1 11.53 20.12 4.06 o 1 0 2 684.94 633.38 2.90 o -2 1 2 49.28 65.26 2.99 o -1 1 2 137.53 147.06 1.70 o 0 1 2 952.35 1161.99 77.93 o 1 1 2 137.76 143.06 1.24 o 2 1 2 49.11 63.66 4.12 o -3 2 2 2.33 2.21 1.55 o -2 2 2 425.22 410.84 4.16 o -1 2 2 344.79 345.50 2.15 o 0 2 2 28.50 33.81 2.14 o 1 2 2 344.63 347.23 2.44 o 2 2 2 425.02 407.91 4.78 o 3 2 2 2.33 0.84 2.72 o -3 3 2 1.66 3.02 2.44 o -2 3 2 27.92 27.13 3.79 o -1 3 2 37.29 42.62 2.38 o 0 3 2 58.72 81.86 1.53 o 1 3 2 37.29 44.95 3.89 o 2 3 2 27.95 32.89 3.88 o 3 3 2 1.65 3.14 2.56 o -4 4 2 3.63 1.10 4.45 o -3 4 2 1.49 8.00 3.55 o -2 4 2 0.04 0.63 1.51 o -1 4 2 60.77 68.58 5.38 o 0 4 2 19.16 20.48 2.01 o 1 4 2 60.70 67.73 4.73 o 2 4 2 0.04 0.65 1.27 o 3 4 2 1.49 2.09 1.81 o -3 5 2 0.36 5.60 3.99 o -2 5 2 1.40 1.55 1.76 o -1 5 2 6.15 10.57 4.84 o 0 5 2 65.50 68.95 6.36 o 1 5 2 6.16 8.61 3.28 o 2 5 2 1.38 1.56 2.30 o 3 5 2 0.35 3.72 2.58 o -1 6 2 5.09 4.62 3.27 o 0 6 2 13.27 10.16 4.74 o 1 6 2 5.10 3.86 3.02 o 1 0 3 34.34 28.60 5.20 o 2 0 3 4.41 9.50 1.88 o -3 1 3 0.10 3.00 2.44 o -2 1 3 31.35 31.30 2.03 o -1 1 3 224.10 194.35 33.25 o 0 1 3 1236.42 1359.95 158.64 o 1 1 3 224.42 214.58 19.28 o 2 1 3 31.33 32.29 2.23 o -3 2 3 45.48 52.50 5.11 o -2 2 3 25.20 15.29 2.16 o -1 2 3 43.80 55.71 1.32 o 0 2 3 287.28 291.14 7.80 o 1 2 3 43.74 59.23 1.26 o 2 2 3 25.22 16.56 5.95 o 3 2 3 45.51 51.53 8.96 o -4 3 3 0.41 0.11 2.77 o -3 3 3 5.77 11.58 5.56 o -2 3 3 29.02 23.30 2.22 o -1 3 3 149.32 147.40 1.99 o 0 3 3 81.24 93.57 1.94 o 1 3 3 149.16 150.71 2.49 o 2 3 3 28.97 23.67 2.53 o 3 3 3 5.76 12.54 8.33 o -4 4 3 4.17 5.53 5.31 o -3 4 3 3.86 3.23 2.55 o -2 4 3 5.99 6.29 2.03 o -1 4 3 2.44 4.27 1.14 o 0 4 3 26.24 23.92 2.40 o 1 4 3 2.44 4.51 1.54 o 2 4 3 6.00 5.41 1.73 o 3 4 3 3.85 2.80 1.50 o -3 5 3 3.89 5.44 3.14 o -2 5 3 0.17 0.01 1.86 o -1 5 3 0.31 0.25 1.67 o 0 5 3 72.24 99.16 5.57 o 1 5 3 0.30 0.27 1.83 o 2 5 3 0.17 0.01 2.13 o 3 5 3 3.87 2.75 3.62 o -1 6 3 14.84 19.04 6.06 o 0 6 3 3.35 4.51 3.53 o 1 6 3 14.82 18.87 7.91 o 1 0 4 584.15 525.78 3.19 o 2 0 4 53.13 46.63 6.32 o 3 0 4 9.53 2.89 6.24 o -3 1 4 49.51 52.99 17.14 o -2 1 4 58.91 59.59 8.96 o -1 1 4 7.03 7.88 0.45 o 0 1 4 175.37 202.94 8.40 o 1 1 4 7.08 7.81 0.30 o 2 1 4 58.77 48.17 11.67 o -4 2 4 0.47 4.03 2.94 o -3 2 4 5.36 3.91 1.40 o -2 2 4 4.86 5.99 1.18 o -1 2 4 4.56 6.21 1.47 o 0 2 4 2.84 3.56 0.71 o 1 2 4 4.58 3.23 1.42 o 2 2 4 4.84 6.91 1.14 o 3 2 4 5.36 2.58 2.66 o -4 3 4 8.37 4.03 2.82 o -3 3 4 44.94 40.09 4.83 o -2 3 4 10.29 8.76 1.90 o -1 3 4 4.20 5.37 1.12 o 0 3 4 3.45 6.37 1.44 o 1 3 4 4.20 5.97 1.30 o 2 3 4 10.31 8.68 1.65 o 3 3 4 44.92 40.13 5.76 o -4 4 4 3.14 0.27 3.86 o -3 4 4 1.09 4.19 4.18 o -2 4 4 16.82 18.48 2.98 o -1 4 4 46.00 58.62 2.34 o 0 4 4 20.75 15.68 2.56 o 1 4 4 45.91 57.90 2.15 o 2 4 4 16.83 12.80 3.05 o 3 4 4 1.08 4.18 4.39 o -3 5 4 1.37 5.58 3.95 o -2 5 4 9.58 9.33 3.89 o -1 5 4 3.42 3.50 1.75 o 0 5 4 6.43 6.35 2.36 o 1 5 4 3.40 5.43 2.29 o 2 5 4 9.55 12.95 3.89 o 3 5 4 1.37 6.00 3.49 o 0 6 4 0.66 0.65 2.76 o 1 0 5 1657.81 1716.12 4.14 o 2 0 5 15.93 9.98 2.26 o 3 0 5 2.04 1.43 1.17 o -3 1 5 31.89 27.14 3.20 o -2 1 5 5.01 3.72 1.76 o -1 1 5 1.23 0.74 0.50 o 0 1 5 197.08 225.83 17.95 o 1 1 5 1.22 0.89 0.42 o 2 1 5 4.97 9.76 1.70 o 3 1 5 31.91 27.48 5.96 o -4 2 5 11.03 9.72 2.65 o -3 2 5 10.94 12.44 3.11 o -2 2 5 166.36 170.03 26.76 o -1 2 5 20.03 15.50 1.82 o 0 2 5 104.18 107.25 0.95 o 1 2 5 20.09 13.56 3.50 o 2 2 5 166.33 203.53 20.28 o 3 2 5 10.96 17.98 5.27 o -4 3 5 0.04 2.87 2.25 o -3 3 5 19.79 17.39 4.36 o -2 3 5 1.98 2.66 1.21 o -1 3 5 5.99 8.10 1.43 o 0 3 5 13.54 9.62 1.52 o 1 3 5 5.97 7.57 1.33 o 2 3 5 1.97 2.19 0.90 o 3 3 5 19.81 17.44 5.15 o 4 3 5 0.04 4.04 5.59 o -4 4 5 0.01 0.01 4.41 o -3 4 5 0.78 4.30 4.62 o -2 4 5 8.09 8.65 1.76 o -1 4 5 64.68 72.05 3.56 o 0 4 5 23.10 24.01 2.46 o 1 4 5 64.68 71.06 3.67 o 2 4 5 8.10 7.77 1.76 o 3 4 5 0.77 4.90 4.11 o 4 4 5 0.01 0.01 6.61 o -3 5 5 1.78 0.47 8.04 o -2 5 5 2.24 3.53 3.20 o -1 5 5 8.27 6.78 2.04 o 0 5 5 16.73 16.07 2.67 o 1 5 5 8.26 6.40 1.97 o 2 5 5 2.23 4.85 3.13 o 3 5 5 1.78 7.23 5.39 o 1 0 6 0.98 1.71 0.39 o 2 0 6 184.61 175.70 36.75 o 3 0 6 11.41 3.80 2.08 o -4 1 6 30.07 28.98 8.27 o -3 1 6 75.28 72.43 2.35 o -2 1 6 245.43 235.16 36.91 o -1 1 6 130.48 125.12 2.39 o 0 1 6 156.75 165.31 7.96 o 1 1 6 130.36 120.60 2.85 o 2 1 6 245.36 211.88 26.40 o 3 1 6 75.29 72.86 2.30 o -4 2 6 2.33 0.00 2.79 o -3 2 6 7.10 8.15 2.28 o -2 2 6 16.16 14.15 2.03 o -1 2 6 1.50 1.29 0.64 o 0 2 6 1.62 1.62 0.90 o 1 2 6 1.52 1.57 0.79 o 2 2 6 16.13 9.81 2.80 o 3 2 6 7.09 5.67 2.14 o -4 3 6 6.24 10.84 5.83 o -3 3 6 46.40 38.90 5.37 o -2 3 6 67.14 68.23 3.83 o -1 3 6 2.16 2.95 0.87 o 0 3 6 60.89 63.13 2.96 o 1 3 6 2.17 3.13 0.88 o 2 3 6 67.19 68.97 5.59 o 3 3 6 46.41 39.02 7.02 o 4 3 6 6.24 10.94 8.07 o -4 4 6 4.79 2.75 8.19 o -3 4 6 2.74 7.73 3.72 o -2 4 6 17.42 22.12 2.26 o -1 4 6 1.42 1.67 1.20 o 0 4 6 4.25 6.39 2.00 o 1 4 6 1.42 3.33 1.57 o 2 4 6 17.40 22.42 2.40 o 3 4 6 2.72 2.66 3.09 o 4 4 6 4.80 0.00 15.01 o -3 5 6 2.84 1.86 4.68 o -2 5 6 18.24 16.52 6.28 o -1 5 6 13.64 15.19 2.28 o 0 5 6 0.11 0.01 1.98 o 1 5 6 13.60 14.65 2.91 o 2 5 6 18.25 21.30 5.05 o 3 5 6 2.84 0.40 6.26 o 1 0 7 164.00 160.95 2.17 o 2 0 7 94.88 79.57 5.53 o 3 0 7 0.54 0.95 0.69 o 4 0 7 41.27 30.59 8.36 o -4 1 7 0.78 2.19 2.20 o -3 1 7 7.13 6.71 1.83 o -2 1 7 36.00 27.07 1.30 o -1 1 7 106.75 122.19 8.87 o 0 1 7 0.03 2.59 1.82 o 1 1 7 106.87 118.52 7.04 o 2 1 7 35.97 26.69 1.47 o 3 1 7 7.13 3.87 2.13 o -4 2 7 8.61 8.58 5.18 o -3 2 7 165.32 135.33 5.50 o -2 2 7 31.08 19.22 2.02 o -1 2 7 37.56 30.42 4.93 o 0 2 7 25.63 35.24 3.89 o 1 2 7 37.54 31.20 2.06 o 2 2 7 31.05 20.22 2.35 o 3 2 7 165.33 125.87 5.39 o 4 2 7 8.61 6.93 3.48 o -4 3 7 0.21 0.23 2.36 o -3 3 7 2.35 5.09 2.41 o -2 3 7 15.53 12.59 2.25 o -1 3 7 21.47 25.48 2.55 o 0 3 7 4.21 2.17 1.14 o 1 3 7 21.43 25.56 3.15 o 2 3 7 15.58 9.98 2.42 o 3 3 7 2.35 4.96 2.75 o 4 3 7 0.21 0.23 3.62 o -4 4 7 9.76 12.57 22.29 o -3 4 7 1.69 4.54 3.08 o -2 4 7 5.78 7.52 2.67 o -1 4 7 11.29 10.42 3.03 o 0 4 7 4.86 4.41 1.56 o 1 4 7 11.29 14.55 4.01 o 2 4 7 5.79 5.83 7.48 o 3 4 7 1.69 3.91 2.40 o 4 4 7 9.77 12.54 11.44 o -2 5 7 2.61 3.94 5.37 o -1 5 7 7.34 7.93 2.49 o 0 5 7 3.77 1.35 1.95 o 1 5 7 7.36 6.19 2.95 o 2 5 7 2.61 5.05 2.62 o 1 0 8 75.24 60.46 14.21 o 2 0 8 3.40 4.50 1.27 o 3 0 8 18.03 11.73 2.24 o 4 0 8 0.89 1.13 1.53 o -4 1 8 11.05 8.01 2.64 o -3 1 8 7.36 6.36 2.24 o -2 1 8 76.46 66.96 2.02 o -1 1 8 119.58 142.25 9.12 o 0 1 8 104.58 85.29 10.21 o 1 1 8 119.53 146.08 6.73 o 2 1 8 76.54 66.29 1.72 o 3 1 8 7.35 7.05 1.81 o 4 1 8 11.05 11.41 9.49 o -5 2 8 0.22 0.45 4.12 o -4 2 8 2.72 5.90 6.04 o -3 2 8 1.03 0.00 2.60 o -2 2 8 9.40 11.15 1.70 o -1 2 8 9.07 6.11 1.44 o 0 2 8 1.21 1.97 0.89 o 1 2 8 9.08 7.61 1.61 o 2 2 8 9.40 10.06 2.18 o 3 2 8 1.04 1.03 0.98 o 4 2 8 2.72 6.61 5.23 o -4 3 8 6.27 8.96 4.33 o -3 3 8 2.29 5.43 1.58 o -2 3 8 58.55 57.50 4.02 o -1 3 8 8.26 8.76 2.32 o 0 3 8 81.51 98.94 4.56 o 1 3 8 8.25 6.34 2.53 o 2 3 8 58.49 57.54 4.09 o 3 3 8 2.30 1.98 2.00 o 4 3 8 6.27 4.58 5.05 o -3 4 8 4.52 4.94 2.79 o -2 4 8 0.39 0.79 2.32 o -1 4 8 15.37 17.84 2.69 o 0 4 8 4.60 2.46 2.05 o 1 4 8 15.39 17.12 3.14 o 2 4 8 0.39 0.98 5.18 o 3 4 8 4.52 4.59 3.15 o -2 5 8 2.16 4.94 4.11 o -1 5 8 15.06 22.33 3.04 o 0 5 8 0.10 0.09 2.46 o 1 5 8 15.07 22.56 3.42 o 2 5 8 2.17 5.74 6.04 o 1 0 9 84.34 80.81 3.03 o 2 0 9 70.90 72.56 6.34 o 3 0 9 1.47 3.17 1.07 o 4 0 9 14.26 10.70 3.76 o -4 1 9 0.72 0.42 2.90 o -3 1 9 3.67 4.82 1.79 o -2 1 9 26.47 27.37 1.94 o -1 1 9 3.35 4.94 1.38 o 1 1 9 3.33 3.45 0.89 o 2 1 9 26.49 27.36 2.42 o 3 1 9 3.68 6.85 2.53 o 4 1 9 0.72 0.32 2.43 o -4 2 9 1.54 3.73 3.26 o -3 2 9 32.28 23.68 3.99 o -2 2 9 23.97 16.79 2.79 o -1 2 9 0.47 2.95 1.64 o 0 2 9 3.19 4.20 1.55 o 1 2 9 0.46 2.72 1.80 o 2 2 9 23.99 18.69 2.55 o 3 2 9 32.26 23.08 3.32 o 4 2 9 1.53 3.77 3.19 o -4 3 9 0.61 0.37 3.75 o -3 3 9 7.11 7.28 3.17 o -2 3 9 11.41 13.76 3.54 o -1 3 9 1.44 2.47 1.55 o 0 3 9 1.71 1.40 1.41 o 1 3 9 1.44 1.19 1.92 o 2 3 9 11.42 10.54 2.73 o 3 3 9 7.10 6.84 2.63 o 4 3 9 0.61 0.31 3.38 o -3 4 9 5.31 6.21 2.83 o -2 4 9 7.59 7.28 3.09 o -1 4 9 12.67 10.92 3.12 o 0 4 9 0.77 2.62 2.22 o 1 4 9 12.68 8.05 3.28 o 2 4 9 7.59 6.31 2.89 o 3 4 9 5.30 5.13 2.88 o -2 5 9 3.95 7.99 3.91 o -1 5 9 2.16 2.24 2.12 o 0 5 9 0.29 0.01 2.73 o 1 5 9 2.15 2.25 3.52 o 2 5 9 3.96 5.39 4.78 o 1 0 10 0.06 2.83 2.85 o 2 0 10 5.10 5.62 1.22 o 3 0 10 4.43 8.97 2.06 o -5 1 10 0.62 3.20 6.61 o -4 1 10 4.74 6.42 2.87 o -3 1 10 10.31 9.03 2.26 o -2 1 10 3.35 3.06 1.48 o -1 1 10 29.00 42.09 6.98 o 1 1 10 29.04 42.38 4.46 o 2 1 10 3.37 3.10 1.30 o 3 1 10 10.30 6.84 1.93 o 4 1 10 4.73 4.76 1.88 o 5 1 10 0.62 4.97 7.38 o -4 2 10 0.00 0.02 2.91 o -3 2 10 2.95 4.11 2.07 o -2 2 10 7.29 8.55 1.79 o -1 2 10 9.74 11.44 1.88 o 0 2 10 0.03 2.56 1.44 o 1 2 10 9.74 11.39 2.48 o 2 2 10 7.30 5.06 1.59 o 3 2 10 2.95 3.57 1.66 o 4 2 10 0.00 0.02 2.22 o -4 3 10 1.13 2.95 3.83 o -3 3 10 9.87 9.72 2.62 o -2 3 10 3.77 4.21 2.16 o -1 3 10 2.51 0.34 2.11 o 0 3 10 1.98 3.17 1.51 o 1 3 10 2.50 1.37 4.43 o 2 3 10 3.77 3.82 2.39 o 3 3 10 9.87 15.05 3.89 o 4 3 10 1.13 3.08 3.62 o -3 4 10 1.41 5.32 3.83 o -2 4 10 4.32 5.63 2.42 o -1 4 10 1.11 0.00 1.72 o 0 4 10 16.52 11.16 3.93 o 1 4 10 1.11 1.28 1.95 o 2 4 10 4.33 4.32 2.69 o 3 4 10 1.42 4.68 3.36 o -1 5 10 7.45 4.58 3.55 o 0 5 10 6.81 5.50 3.02 o 1 5 10 7.47 5.77 3.43 o 1 0 11 4.39 0.00 5.54 o 2 0 11 7.55 7.60 1.69 o 3 0 11 2.61 2.39 1.78 o 4 0 11 0.02 1.99 3.03 o -4 1 11 0.49 0.61 3.10 o -3 1 11 5.53 5.54 1.83 o -2 1 11 10.91 8.69 2.55 o -1 1 11 39.45 39.20 12.49 o 1 1 11 39.39 36.41 2.45 o 2 1 11 10.93 9.47 4.14 o 3 1 11 5.52 8.80 2.19 o 4 1 11 0.49 0.58 1.81 o -4 2 11 2.39 2.27 3.22 o -3 2 11 0.31 0.01 2.95 o -2 2 11 14.32 13.18 2.05 o -1 2 11 2.35 2.10 2.94 o 0 2 11 0.49 1.47 2.21 o 1 2 11 2.34 4.45 1.66 o 2 2 11 14.33 20.78 3.59 o 3 2 11 0.30 0.02 2.13 o 4 2 11 2.38 2.32 4.22 o -3 3 11 1.96 8.58 3.09 o -2 3 11 5.24 5.34 2.94 o -1 3 11 22.44 18.73 4.74 o 0 3 11 3.51 3.76 1.75 o 1 3 11 22.51 17.47 5.61 o 2 3 11 5.23 7.21 2.46 o 3 3 11 1.97 5.29 2.65 o -3 4 11 1.64 0.98 3.19 o -2 4 11 2.84 5.17 3.24 o -1 4 11 0.66 3.89 2.64 o 0 4 11 2.23 4.38 2.81 o 1 4 11 0.66 3.09 2.89 o 2 4 11 2.83 5.29 3.26 o 3 4 11 1.64 0.94 2.78 o 0 5 11 4.81 3.13 2.76 o 1 0 12 36.06 37.31 7.63 o 2 0 12 1.11 3.40 1.85 o 3 0 12 6.80 6.68 2.70 o 4 0 12 2.51 3.54 2.18 o -4 1 12 0.50 0.71 1.88 o -3 1 12 1.46 1.97 2.55 o -2 1 12 1.51 3.58 1.77 o -1 1 12 5.14 5.50 3.89 o 1 1 12 5.15 3.33 1.41 o 2 1 12 1.51 2.73 2.07 o 3 1 12 1.46 1.97 1.89 o 4 1 12 0.50 0.66 2.40 o -4 2 12 3.33 6.84 2.69 o -3 2 12 2.14 3.78 1.85 o -2 2 12 28.59 23.26 3.37 o -1 2 12 1.87 0.00 5.72 o 1 2 12 1.87 1.00 1.92 o 2 2 12 28.60 22.52 4.06 o 3 2 12 2.14 3.26 2.17 o 4 2 12 3.33 5.58 2.72 o -3 3 12 2.81 5.17 3.60 o -2 3 12 3.03 3.06 10.40 o -1 3 12 0.99 7.82 6.15 o 0 3 12 8.79 4.92 1.92 o 1 3 12 0.98 5.36 2.61 o 2 3 12 3.04 3.03 3.14 o 3 3 12 2.81 4.04 2.83 o -2 4 12 1.12 4.61 3.37 o -1 4 12 6.75 7.27 2.94 o 0 4 12 19.99 19.49 7.63 o 1 4 12 6.76 3.34 4.40 o 2 4 12 1.12 3.01 2.34 o 2 0 13 1.36 2.44 1.62 o 3 0 13 0.42 3.46 3.06 o 4 0 13 0.12 0.13 2.55 o -4 1 13 0.08 0.05 2.04 o -3 1 13 0.82 0.45 1.94 o -2 1 13 1.58 1.92 1.68 o 1 1 13 33.89 35.62 3.98 o 2 1 13 1.58 2.33 2.03 o 3 1 13 0.83 0.51 2.17 o 4 1 13 0.09 0.04 2.41 o -3 2 13 0.10 0.57 2.27 o -2 2 13 0.76 1.58 2.58 o -1 2 13 20.20 20.51 9.77 o 1 2 13 20.21 20.76 4.65 o 2 2 13 0.76 2.47 3.90 o 3 2 13 0.10 0.50 3.40 o -3 3 13 0.10 0.17 3.63 o -2 3 13 0.50 0.99 4.21 o -1 3 13 23.48 27.12 11.34 o 0 3 13 10.92 5.06 2.15 o 1 3 13 23.49 23.98 5.91 o 2 3 13 0.50 0.99 4.07 o 3 3 13 0.10 0.21 2.69 o -2 4 13 0.36 1.38 5.09 o -1 4 13 0.37 4.33 4.21 o 0 4 13 0.05 1.57 4.51 o 1 4 13 0.37 4.69 3.98 o 2 4 13 0.36 3.36 3.36 o 2 0 14 5.28 11.23 3.59 o 3 0 14 4.22 4.66 2.37 o 4 0 14 0.06 0.28 2.25 o -3 1 14 0.15 0.12 1.89 o -2 1 14 2.32 5.54 3.90 o 2 1 14 2.33 2.44 3.67 o 3 1 14 0.15 0.23 1.87 o -3 2 14 1.51 4.94 2.82 o -2 2 14 19.40 21.57 6.93 o 1 2 14 6.07 3.80 3.85 o 2 2 14 19.40 15.40 9.90 o 3 2 14 1.51 2.42 3.41 o -2 3 14 2.78 7.24 4.96 o -1 3 14 0.39 3.65 5.09 o 1 3 14 0.39 2.23 3.70 o 2 3 14 2.77 7.15 9.00 o -1 4 14 6.97 5.06 5.20 o 1 4 14 6.98 5.82 4.20 o 2 0 15 0.82 7.41 5.21 o 3 0 15 0.35 3.17 2.29 o -3 1 15 2.42 5.04 2.47 o -2 1 15 2.69 5.09 5.43 o 2 1 15 2.69 3.48 2.67 o 3 1 15 2.42 4.62 2.45 o -3 2 15 0.63 3.59 4.84 o -2 2 15 0.61 0.30 3.55 o 1 2 15 0.56 5.01 3.17 o 2 2 15 0.61 0.34 3.09 o 3 2 15 0.63 4.38 3.80 o -2 3 15 2.21 3.97 4.37 o 1 3 15 5.72 5.13 4.70 o 2 3 15 2.21 3.42 5.63 o 2 0 16 0.00 3.99 4.10 o 3 0 16 0.06 4.05 5.10 o -3 1 16 0.59 0.08 3.73 o 2 1 16 0.01 4.06 3.24 o 3 1 16 0.59 0.09 4.79 o 2 2 16 0.63 4.73 5.74 o 1 3 16 0.55 1.97 4.94 o 2 1 17 0.60 0.00 3.55 o ################################################################## data_2but_2.33GPa _database_code_depnum_ccdc_archive 'CCDC 870126' #TrackingRef '- All.cif' # CHEMICAL DATA _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-butanol ; _chemical_name_common 2-butanol _chemical_melting_point 158 _chemical_formula_moiety 'C4 H10 O' _chemical_formula_sum 'C4 H10 O' _chemical_formula_weight 74.12 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' # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _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 5.0122(10) _cell_length_b 5.0885(10) _cell_length_c 16.044(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 409.20(14) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2975 _cell_measurement_theta_min 4.20 _cell_measurement_theta_max 24.92 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.203 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 168 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.41 _exptl_absorpt_correction_T_max 0.88 _exptl_absorpt_process_details ; Correction for absorption of the diamond-anvil cell and the sample were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam Mickiewicz University Pozna\'n; Katrusiak, A. (2004) Z. Kristallogr. 219, 461-467). ; # EXPERIMENTAL DATA _exptl_special_details ; Data were collected at room temperature and pressure of 2.33(5) GPa (2330000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line. ; _diffrn_ambient_temperature 295(2) _diffrn_ambient_environment 'diamond-anvil cell' _diffrn_ambient_pressure 2330000 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KM-4 CCD' _diffrn_measurement_method '\f- and \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 2975 _diffrn_reflns_av_R_equivalents 0.1644 _diffrn_reflns_av_sigmaI/netI 0.0779 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.20 _diffrn_reflns_theta_max 24.92 _reflns_number_total 408 _reflns_number_gt 304 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisCCD (Oxford Diffraction, 2004)' _computing_cell_refinement 'CrysAlisRED (Oxford Diffraction, 2004)' _computing_data_reduction 'CrysAlisRED (Oxford Diffraction, 2004); REDSHABS (Katrusiak, A. 2003)' _computing_structure_solution 'SHELXS--97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL--97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1990)' _computing_publication_material 'SHELXL--97 (Sheldrick, 1997)' # REFINEMENT DATA _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. The DAC imposes severe restrictions on which reflections can be collected, resulting in a low data:parameter ratio. The relatively high R factors are due to the low quality of the crystal sample. Generally it was difficult to grow single crystals of this substance, and despite multiple tries the quality of the single crystal could not be improved. ; _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^)+(0.1937P)^2^+0.1060P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -5(9) _refine_ls_number_reflns 408 _refine_ls_number_parameters 46 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.1301 _refine_ls_R_factor_gt 0.1118 _refine_ls_wR_factor_ref 0.3005 _refine_ls_wR_factor_gt 0.2797 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.146 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 O1 O 0.0644(16) 0.3214(10) 0.7751(4) 0.068(2) Uani 1 1 d U . . H1 H 0.0102 0.4629 0.7574 0.102 Uiso 1 1 calc R . . C1 C -0.112(2) 0.6155(12) 0.9256(6) 0.060(3) Uani 1 1 d U . . H11 H -0.2020 0.6166 0.9784 0.089 Uiso 1 1 calc R . . H12 H -0.2400 0.5941 0.8816 0.089 Uiso 1 1 calc R . . H13 H -0.0186 0.7786 0.9182 0.089 Uiso 1 1 calc R . . C2 C 0.088(2) 0.3870(12) 0.9233(6) 0.057(3) Uani 1 1 d U . . H21 H 0.2155 0.4093 0.9683 0.068 Uiso 1 1 calc R . . H22 H -0.0068 0.2239 0.9330 0.068 Uiso 1 1 calc R . . C3 C 0.2394(19) 0.3651(12) 0.8422(5) 0.046(2) Uani 1 1 d U . . H31 H 0.3432 0.5254 0.8325 0.055 Uiso 1 1 calc R . . C4 C 0.4241(17) 0.1284(12) 0.8453(5) 0.046(2) Uani 1 1 d U . . H41 H 0.5216 0.1161 0.7940 0.069 Uiso 1 1 calc R . . H42 H 0.3205 -0.0284 0.8532 0.069 Uiso 1 1 calc R . . H43 H 0.5468 0.1480 0.8909 0.069 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 O1 0.079(6) 0.036(3) 0.090(7) 0.007(3) -0.025(3) -0.004(3) C1 0.073(6) 0.029(3) 0.077(5) 0.003(3) 0.001(3) 0.011(3) C2 0.090(8) 0.025(3) 0.055(8) -0.003(4) -0.005(4) 0.007(4) C3 0.054(7) 0.025(3) 0.060(7) -0.003(3) -0.016(4) 0.007(4) C4 0.045(7) 0.032(3) 0.062(6) 0.004(3) 0.012(3) 0.003(4) # MOLECULAR GEOMETRY _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 O1 C3 1.406(10) . ? O1 H1 0.8200 . ? C1 C2 1.537(11) . ? C1 H11 0.9600 . ? C1 H12 0.9600 . ? C1 H13 0.9600 . ? C2 C3 1.509(14) . ? C2 H21 0.9700 . ? C2 H22 0.9700 . ? C3 C4 1.520(9) . ? C3 H31 0.9800 . ? C4 H41 0.9600 . ? C4 H42 0.9600 . ? C4 H43 0.9600 . ? 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 C3 O1 H1 109.5 . . ? C2 C1 H11 109.5 . . ? C2 C1 H12 109.5 . . ? H11 C1 H12 109.5 . . ? C2 C1 H13 109.5 . . ? H11 C1 H13 109.5 . . ? H12 C1 H13 109.5 . . ? C3 C2 C1 113.8(7) . . ? C3 C2 H21 108.8 . . ? C1 C2 H21 108.8 . . ? C3 C2 H22 108.8 . . ? C1 C2 H22 108.8 . . ? H21 C2 H22 107.7 . . ? O1 C3 C2 111.0(10) . . ? O1 C3 C4 106.3(6) . . ? C2 C3 C4 109.6(6) . . ? O1 C3 H31 110.0 . . ? C2 C3 H31 110.0 . . ? C4 C3 H31 110.0 . . ? C3 C4 H41 109.5 . . ? C3 C4 H42 109.5 . . ? H41 C4 H42 109.5 . . ? C3 C4 H43 109.5 . . ? H41 C4 H43 109.5 . . ? H42 C4 H43 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 C1 C2 C3 O1 -61.0(9) . . . . ? C1 C2 C3 C4 -178.1(7) . . . . ? _diffrn_measured_fraction_theta_max 0.551 _diffrn_reflns_theta_full 24.92 _diffrn_measured_fraction_theta_full 0.551 _refine_diff_density_max 0.325 _refine_diff_density_min -0.385 _refine_diff_density_rms 0.087 # # h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag # loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_squared_calc _refln_F_squared_meas _refln_F_squared_sigma _refln_observed_status 1 1 0 53.47 79.19 2.87 o 0 2 0 69.91 71.31 1.89 o 1 2 0 796.09 734.18 9.23 o 1 3 0 58.48 53.50 1.12 o 2 3 0 26.49 21.84 4.55 o 0 4 0 566.85 825.88 16.59 o 1 4 0 42.70 46.59 4.30 o 2 4 0 2.13 0.90 1.01 o 1 5 0 0.94 4.31 1.58 o 2 5 0 5.64 3.13 2.67 o 0 6 0 3.27 3.16 2.19 o 1 0 1 563.87 578.28 53.75 o -1 1 1 1593.26 1922.00 119.21 o 0 1 1 413.50 496.39 13.11 o 1 1 1 1593.74 1796.19 87.58 o -2 2 1 17.03 11.66 2.99 o -1 2 1 488.69 555.33 12.56 o 0 2 1 169.13 155.36 1.19 o 1 2 1 488.17 533.75 12.06 o 2 2 1 17.06 11.21 3.56 o -2 3 1 82.85 93.46 11.53 o -1 3 1 187.64 270.13 4.66 o 0 3 1 25.81 14.22 2.04 o 1 3 1 187.73 248.97 7.84 o 2 3 1 82.89 98.94 7.29 o -2 4 1 6.71 8.42 1.40 o -1 4 1 2.99 5.93 1.09 o 0 4 1 65.63 93.41 1.90 o 1 4 1 2.97 4.72 1.04 o 2 4 1 6.75 9.23 2.43 o -2 5 1 0.76 3.66 2.75 o -1 5 1 63.29 74.62 2.85 o 0 5 1 17.66 17.47 2.46 o 1 5 1 63.34 73.67 2.72 o 2 5 1 0.75 4.56 3.76 o 0 6 1 0.73 2.42 2.08 o 1 0 2 688.61 603.64 17.73 o -2 1 2 65.75 72.36 4.24 o -1 1 2 76.59 55.90 5.73 o 0 1 2 688.25 1056.66 37.80 o 1 1 2 76.75 56.58 4.73 o 2 1 2 65.53 82.21 14.52 o -2 2 2 392.25 496.57 53.32 o -1 2 2 276.17 360.91 27.51 o 0 2 2 100.45 172.14 5.09 o 1 2 2 276.06 299.60 27.02 o 2 2 2 391.89 507.63 29.81 o -2 3 2 75.84 84.19 4.25 o -1 3 2 51.00 72.62 2.84 o 0 3 2 108.39 131.86 3.85 o 1 3 2 50.96 69.17 1.92 o 2 3 2 75.73 81.15 7.55 o -2 4 2 1.16 3.07 1.32 o -1 4 2 74.42 73.57 3.54 o 0 4 2 0.70 0.41 0.92 o 1 4 2 74.26 79.64 4.58 o 2 4 2 1.17 2.56 1.17 o -2 5 2 4.11 6.04 2.41 o -1 5 2 2.42 5.17 1.44 o 0 5 2 21.36 19.06 2.24 o 1 5 2 2.40 4.43 1.25 o 2 5 2 4.09 3.00 1.81 o 0 6 2 18.01 17.32 2.58 o 1 0 3 39.37 51.06 0.41 o 2 0 3 17.24 16.56 1.68 o -2 1 3 16.19 16.55 2.02 o -1 1 3 210.28 178.95 1.93 o 0 1 3 1250.74 1301.25 5.46 o 1 1 3 210.57 179.69 1.87 o 2 1 3 16.20 13.52 1.50 o -2 2 3 46.84 45.47 3.91 o -1 2 3 71.88 102.20 1.97 o 0 2 3 203.83 236.78 1.48 o 1 2 3 71.80 102.62 2.38 o 2 2 3 46.89 48.31 4.57 o -3 3 3 35.36 31.61 3.62 o -2 3 3 21.53 25.25 1.92 o -1 3 3 175.98 256.38 13.54 o 0 3 3 65.87 76.24 2.97 o 1 3 3 175.86 257.53 9.08 o 2 3 3 21.53 26.22 2.43 o -3 4 3 6.12 6.87 4.48 o -2 4 3 17.86 19.42 1.86 o -1 4 3 35.48 48.74 1.53 o 0 4 3 45.72 42.89 3.02 o 1 4 3 35.52 44.16 1.56 o 2 4 3 17.90 19.26 1.76 o -2 5 3 4.63 2.49 1.86 o -1 5 3 2.17 3.25 1.23 o 0 5 3 64.50 79.15 3.72 o 1 5 3 2.16 2.24 1.22 o 2 5 3 4.61 4.63 1.86 o 1 0 4 611.28 522.35 1.80 o 2 0 4 67.27 60.78 1.13 o 3 0 4 17.46 12.44 3.71 o -3 1 4 46.15 58.82 4.85 o -2 1 4 83.42 112.82 2.51 o -1 1 4 14.01 7.09 0.30 o 1 1 4 14.05 7.24 0.45 o 2 1 4 83.25 108.29 1.47 o 3 1 4 46.22 46.82 7.64 o -3 2 4 4.38 1.94 1.20 o -2 2 4 21.38 26.16 2.97 o -1 2 4 2.43 1.66 0.59 o 0 2 4 59.25 82.97 2.80 o 1 2 4 2.46 1.70 0.59 o 2 2 4 21.46 27.55 3.63 o 3 2 4 4.38 5.38 1.87 o -3 3 4 59.18 74.27 6.46 o -2 3 4 14.52 11.48 2.06 o -1 3 4 17.64 17.58 1.28 o 0 3 4 0.22 2.25 0.64 o 1 3 4 17.59 21.40 1.72 o 2 3 4 14.48 13.16 2.00 o 3 3 4 59.16 72.97 23.13 o -3 4 4 0.82 3.10 2.98 o -2 4 4 16.05 16.18 2.46 o -1 4 4 44.09 51.37 3.55 o 0 4 4 74.78 84.67 4.22 o 1 4 4 43.97 53.80 5.03 o 2 4 4 16.06 13.88 2.19 o 3 4 4 0.83 1.25 2.75 o -3 5 4 0.09 2.98 2.86 o -2 5 4 17.70 16.81 3.56 o -1 5 4 2.49 2.81 1.26 o 0 5 4 72.94 106.73 3.13 o 1 5 4 2.48 3.68 1.25 o 2 5 4 17.68 18.33 3.31 o 1 0 5 1896.15 1311.95 210.62 o 2 0 5 12.21 11.24 3.02 o 3 0 5 0.55 0.47 0.62 o -3 1 5 68.73 61.27 2.30 o -2 1 5 19.75 22.22 7.66 o -1 1 5 8.78 5.87 0.36 o 1 1 5 8.75 5.71 0.46 o 2 1 5 19.67 17.94 3.50 o 3 1 5 68.76 60.56 2.32 o -3 2 5 23.17 11.93 1.68 o -2 2 5 204.39 156.65 24.87 o -1 2 5 25.99 29.28 6.02 o 0 2 5 77.48 80.91 2.66 o 1 2 5 26.07 35.50 6.36 o 2 2 5 204.31 192.60 20.63 o 3 2 5 23.19 16.14 2.49 o -3 3 5 6.25 2.99 1.39 o -2 3 5 4.88 4.86 1.03 o -1 3 5 7.88 10.97 1.30 o 0 3 5 0.24 1.81 0.68 o 1 3 5 7.87 8.54 1.26 o 2 3 5 4.84 4.85 1.21 o 3 3 5 6.27 3.60 2.98 o -3 4 5 5.69 4.67 2.49 o -2 4 5 7.19 8.48 2.40 o -1 4 5 80.07 119.57 6.87 o 0 4 5 9.08 3.63 1.24 o 1 4 5 80.03 111.72 4.84 o 2 4 5 7.20 6.18 2.13 o 3 4 5 5.69 4.16 2.06 o -2 5 5 8.38 6.40 2.69 o -1 5 5 29.95 19.82 2.92 o 0 5 5 8.18 6.18 1.57 o 1 5 5 29.89 19.99 3.29 o 2 5 5 8.36 8.45 3.23 o 1 0 6 0.67 0.62 0.49 o 2 0 6 237.71 147.22 15.37 o 3 0 6 10.09 7.88 1.12 o -3 1 6 82.39 74.87 8.93 o -2 1 6 273.68 246.45 9.60 o -1 1 6 171.69 126.08 21.27 o 1 1 6 171.57 198.80 35.74 o 2 1 6 273.60 259.19 6.32 o 3 1 6 82.44 80.86 8.80 o -3 2 6 8.59 10.39 3.24 o -2 2 6 21.95 13.30 0.94 o -1 2 6 2.19 0.93 0.52 o 1 2 6 2.21 1.08 0.91 o 2 2 6 21.95 14.86 1.19 o 3 2 6 8.57 7.55 1.92 o -3 3 6 52.63 40.82 3.62 o -2 3 6 98.73 132.28 3.25 o -1 3 6 0.51 0.10 0.88 o 0 3 6 81.95 84.75 5.36 o 1 3 6 0.51 0.07 1.01 o 2 3 6 98.88 130.00 5.39 o 3 3 6 52.64 41.16 3.66 o -3 4 6 0.00 2.98 1.83 o -2 4 6 14.91 20.58 2.68 o -1 4 6 6.21 4.77 1.36 o 0 4 6 0.17 1.18 1.18 o 1 4 6 6.24 3.52 1.67 o 2 4 6 14.86 20.98 2.18 o 3 4 6 0.00 2.66 1.99 o -2 5 6 12.28 11.58 2.72 o -1 5 6 8.25 7.03 2.20 o 0 5 6 0.08 0.08 1.90 o 1 5 6 8.25 6.21 2.97 o 2 5 6 12.31 5.42 2.51 o 1 0 7 158.66 101.78 8.52 o 2 0 7 99.09 121.10 1.81 o 3 0 7 0.79 1.85 0.67 o 4 0 7 47.14 50.05 4.81 o -4 1 7 0.17 0.90 1.46 o -3 1 7 12.27 13.76 1.99 o -2 1 7 57.83 58.76 7.00 o -1 1 7 97.14 101.37 12.69 o 1 1 7 97.25 110.41 11.46 o 2 1 7 57.80 57.68 5.98 o 3 1 7 12.26 16.02 2.67 o 4 1 7 0.17 1.21 3.18 o -4 2 7 12.77 13.91 3.51 o -3 2 7 220.62 215.37 5.70 o -2 2 7 42.31 40.61 5.91 o -1 2 7 39.12 41.45 4.66 o 1 2 7 39.07 36.22 4.11 o 2 2 7 42.24 43.78 4.98 o 3 2 7 220.64 219.86 4.01 o 4 2 7 12.79 13.66 2.97 o -4 3 7 0.04 3.13 3.53 o -3 3 7 1.50 2.96 1.33 o -2 3 7 1.06 3.49 1.39 o -1 3 7 47.70 53.28 5.46 o 1 3 7 47.65 53.70 2.96 o 2 3 7 1.07 1.92 1.10 o 3 3 7 1.51 4.13 1.46 o -3 4 7 3.09 4.83 1.92 o -2 4 7 4.56 3.65 1.95 o -1 4 7 6.03 14.10 2.53 o 0 4 7 2.02 2.73 1.32 o 1 4 7 6.01 10.88 2.22 o 2 4 7 4.55 4.06 2.23 o 3 4 7 3.10 3.42 1.53 o -2 5 7 6.06 4.78 2.35 o -1 5 7 4.20 3.49 2.83 o 0 5 7 6.16 13.72 10.20 o 1 5 7 4.18 3.46 2.51 o 2 5 7 6.06 4.86 2.63 o 1 0 8 102.41 70.62 8.55 o 2 0 8 4.20 1.89 0.76 o 3 0 8 18.19 17.35 2.84 o 4 0 8 1.72 2.78 1.64 o -4 1 8 15.55 11.84 3.43 o -3 1 8 9.43 5.69 1.81 o -2 1 8 92.88 98.04 1.40 o -1 1 8 133.38 201.94 17.27 o 1 1 8 133.28 171.86 18.78 o 2 1 8 92.98 100.03 1.84 o 3 1 8 9.43 8.34 1.61 o 4 1 8 15.54 10.33 4.79 o -4 2 8 1.99 4.75 2.25 o -3 2 8 5.39 1.85 1.31 o -2 2 8 7.51 8.00 1.21 o -1 2 8 7.03 5.42 0.97 o 1 2 8 7.03 5.20 1.52 o 2 2 8 7.49 7.63 1.22 o 3 2 8 5.40 3.29 1.39 o 4 2 8 1.99 2.96 1.99 o -4 3 8 9.67 9.23 3.14 o -3 3 8 1.89 1.76 1.91 o -2 3 8 92.94 100.53 3.64 o -1 3 8 5.55 3.02 0.84 o 1 3 8 5.56 3.15 1.96 o 2 3 8 92.89 96.45 3.49 o 3 3 8 1.90 1.82 1.66 o 4 3 8 9.67 6.58 2.96 o -3 4 8 0.55 0.24 1.51 o -2 4 8 0.98 2.86 1.67 o -1 4 8 23.51 18.86 3.35 o 1 4 8 23.54 18.08 4.15 o 2 4 8 0.99 3.51 1.57 o 3 4 8 0.55 0.25 1.24 o -2 5 8 2.92 3.45 2.03 o -1 5 8 9.56 5.16 2.75 o 1 5 8 9.56 8.36 2.79 o 2 5 8 2.92 4.55 2.38 o 1 0 9 127.26 159.07 5.30 o 2 0 9 88.27 66.25 8.20 o 3 0 9 1.53 3.45 1.10 o 4 0 9 17.83 25.02 5.64 o -4 1 9 1.68 3.76 1.61 o -3 1 9 5.11 5.29 1.59 o -2 1 9 41.86 58.56 7.40 o -1 1 9 3.57 2.44 1.77 o 1 1 9 3.56 2.18 1.33 o 2 1 9 41.90 48.64 11.51 o 3 1 9 5.12 7.06 1.90 o 4 1 9 1.68 4.76 2.33 o -4 2 9 2.50 3.66 1.72 o -3 2 9 36.11 20.36 3.92 o -2 2 9 25.79 19.42 3.08 o -1 2 9 6.02 8.02 3.85 o 1 2 9 6.03 4.46 1.70 o 2 2 9 25.84 20.13 2.00 o 3 2 9 36.10 40.97 6.02 o 4 2 9 2.49 3.34 1.89 o -4 3 9 0.75 2.20 1.68 o -3 3 9 10.91 8.00 2.33 o -2 3 9 7.00 4.11 1.72 o -1 3 9 4.26 2.71 1.75 o 1 3 9 4.22 2.07 1.15 o 2 3 9 7.01 8.32 2.87 o 3 3 9 10.90 8.18 2.65 o 4 3 9 0.75 3.76 2.14 o -3 4 9 5.28 6.35 2.03 o -2 4 9 5.40 3.32 1.57 o -1 4 9 34.49 39.28 7.47 o 1 4 9 34.53 38.96 4.70 o 2 4 9 5.40 3.16 1.32 o 3 4 9 5.28 6.03 1.80 o -1 5 9 16.10 13.24 10.13 o 1 5 9 16.10 12.78 4.52 o 2 0 10 7.61 6.85 1.50 o 3 0 10 11.00 9.33 2.44 o 4 0 10 0.16 4.22 2.15 o -4 1 10 5.95 4.28 1.73 o -3 1 10 17.94 24.83 1.43 o -2 1 10 2.74 3.03 1.42 o 2 1 10 2.76 2.60 1.07 o 3 1 10 17.91 24.16 1.68 o 4 1 10 5.94 5.14 1.62 o -4 2 10 1.09 0.39 1.89 o -3 2 10 5.38 4.42 1.52 o -2 2 10 20.34 13.53 1.78 o -1 2 10 9.69 15.18 4.68 o 1 2 10 9.68 6.42 2.88 o 2 2 10 20.33 13.64 2.82 o 3 2 10 5.38 5.01 1.81 o 4 2 10 1.09 0.37 1.68 o -4 3 10 2.25 4.84 2.11 o -3 3 10 13.54 15.16 3.79 o -2 3 10 8.00 8.18 2.27 o 1 3 10 4.26 5.60 1.58 o 2 3 10 7.98 7.07 1.73 o 3 3 10 13.53 8.47 2.98 o 4 3 10 2.25 4.34 2.11 o -3 4 10 0.85 4.13 1.95 o -2 4 10 9.69 7.20 2.64 o -1 4 10 2.88 2.33 3.68 o 1 4 10 2.88 2.66 2.94 o 2 4 10 9.70 11.48 2.24 o 3 4 10 0.85 2.41 1.52 o 2 0 11 7.19 9.12 1.51 o 3 0 11 3.38 5.60 1.62 o 4 0 11 0.05 2.82 1.52 o -4 1 11 1.83 0.80 1.74 o -3 1 11 6.72 5.83 1.71 o -2 1 11 12.96 7.35 2.96 o 2 1 11 12.99 11.82 2.11 o 3 1 11 6.71 4.81 1.68 o 4 1 11 1.83 0.83 1.59 o -4 2 11 7.00 5.92 2.43 o -3 2 11 1.14 3.61 1.79 o -2 2 11 25.98 34.20 4.74 o 2 2 11 26.01 33.60 4.79 o 3 2 11 1.13 5.40 1.90 o 4 2 11 6.98 11.88 2.82 o -3 3 11 5.58 8.78 2.93 o -2 3 11 4.63 7.16 2.38 o 2 3 11 4.64 5.44 2.66 o 3 3 11 5.59 8.43 2.82 o -2 4 11 2.03 2.62 3.77 o 2 4 11 2.03 3.24 2.59 o 2 0 12 2.05 1.33 0.97 o 3 0 12 7.55 9.08 2.53 o 4 0 12 2.45 4.02 2.36 o -4 1 12 0.17 0.09 1.62 o -3 1 12 4.94 4.06 1.58 o -2 1 12 1.93 1.07 1.99 o 2 1 12 1.93 1.06 1.21 o 3 1 12 4.94 4.36 1.52 o 4 1 12 0.17 0.07 1.82 o -4 2 12 5.35 6.35 2.63 o -3 2 12 1.44 3.75 1.52 o -2 2 12 39.51 46.35 16.74 o 2 2 12 39.52 62.01 16.28 o 3 2 12 1.44 3.25 1.50 o 4 2 12 5.35 7.59 2.35 o -3 3 12 5.28 6.96 3.50 o -2 3 12 2.75 1.96 3.07 o 2 3 12 2.77 5.46 2.97 o 3 3 12 5.28 4.43 2.31 o -2 4 12 1.91 1.85 3.34 o 2 4 12 1.91 1.18 4.48 o 2 0 13 0.05 1.36 1.28 o 3 0 13 0.01 3.49 2.04 o 4 0 13 0.42 2.69 1.70 o -4 1 13 0.29 0.02 1.79 o -3 1 13 2.07 4.50 1.46 o -2 1 13 0.74 1.75 1.65 o 2 1 13 0.74 2.05 2.01 o 3 1 13 2.08 4.30 1.49 o 4 1 13 0.29 0.07 2.23 o -3 2 13 0.28 0.29 1.93 o 2 2 13 3.62 3.62 2.48 o 3 2 13 0.27 0.34 1.60 o -3 3 13 0.26 3.14 2.04 o 2 3 13 0.03 5.71 4.07 o 3 3 13 0.26 2.29 2.22 o 3 0 14 2.37 4.08 3.75 o 4 0 14 0.14 0.59 1.90 o -3 1 14 0.09 2.83 1.54 o 3 1 14 0.09 2.30 1.55 o -3 2 14 1.11 2.24 2.19 o 3 2 14 1.12 2.43 1.50 o 3 0 15 0.67 1.40 3.03 o -3 1 15 3.38 3.00 2.74 o 3 1 15 3.38 4.08 2.38 o -3 2 15 6.15 1.66 2.93 o 3 2 15 6.14 2.26 6.27 o ##################################################################