# 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 BA cif files.txt' _publ_contact_author_name 'Andrzej Katrusiak' _publ_contact_author_address ;Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznan Poland ; _publ_contact_author_fax +48(61)8291505 _publ_contact_author_phone +48(61)8291443 _publ_contact_author_email katran@amu.edu.pl _publ_section_title ; ? ; loop_ _publ_author_footnote ; Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznan Poland ; _publ_author_address ;Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznan Poland ; loop_ _publ_author_name 'Weizhao Cai.' 'Andrzej Katrusiak' #++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ data_benziocacid_0.64GPa(CCDC864018) _database_code_depnum_ccdc_archive 'CCDC 864018' #TrackingRef '- All BA cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'benzioc acid' _chemical_melting_point ? _chemical_formula_moiety 'C7 H6 O2' _chemical_formula_sum 'C7 H6 O2' _chemical_formula_weight 122.12 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-p 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.2959(8) _cell_length_b 5.0110(8) _cell_length_c 21.651(14) _cell_angle_alpha 90.00 _cell_angle_beta 98.78(4) _cell_angle_gamma 90.00 _cell_volume 567.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_pressure 640000 _cell_measurement_reflns_used 2300 _cell_measurement_theta_min 4.49 _cell_measurement_theta_max 28.41 _exptl_crystal_description plate-shaped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.433 _exptl_absorpt_correction_T_max 0.923 _exptl_absorpt_process_details ; Katrusiak, A. (2003). REDSHABS - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Pozna\'n. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 ; _exptl_special_details ; Data were collected at room temperature and pressure of 0.64(3) GPa (640000 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 296(2) _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 'Kuma KM4CCD \k geometry' _diffrn_measurement_method ;HP omega scans - for more details see: A. Budzianowski, A. Katrusiak in High-Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168 ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2300 _diffrn_reflns_av_R_equivalents 0.2105 _diffrn_reflns_av_sigmaI/netI 0.0900 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 4.49 _diffrn_reflns_theta_max 28.41 _reflns_number_total 201 _reflns_number_gt 180 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2004)' _computing_cell_refinement 'CrysAlis (Oxford Diffraction, 2004)' _computing_data_reduction 'CrysAlisRED (Oxford Diffraction, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury (Macrae et al., 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0548P)^2^+0.8397P] 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_number_reflns 201 _refine_ls_number_parameters 82 _refine_ls_number_restraints 113 _refine_ls_R_factor_all 0.1081 _refine_ls_R_factor_gt 0.0927 _refine_ls_wR_factor_ref 0.1883 _refine_ls_wR_factor_gt 0.1775 _refine_ls_goodness_of_fit_ref 1.211 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2303(10) 0.2437(10) 0.0130(7) 0.060(5) Uani 1 1 d DU . . H6A H 0.1728 0.1146 -0.0078 0.090 Uiso 0.76(13) 1 calc PR . . O2 O -0.0992(9) 0.1465(10) 0.0651(7) 0.057(4) Uani 1 1 d U . . H6 H -0.1287 0.0301 0.0384 0.086 Uiso 0.24(13) 1 calc PR . . C1 C 0.1032(14) 0.2816(12) 0.0560(13) 0.041(4) Uani 1 1 d U . . C2 C 0.1792(16) 0.4924(12) 0.1025(14) 0.041(4) Uani 1 1 d U . . C3 C 0.3898(14) 0.6563(15) 0.1033(10) 0.050(4) Uani 1 1 d U . . H1 H 0.4923 0.6244 0.0728 0.060 Uiso 1 1 calc R . . C4 C 0.4599(15) 0.8504(14) 0.1421(14) 0.044(4) Uani 1 1 d U . . H2 H 0.5954 0.9619 0.1368 0.053 Uiso 1 1 calc R . . C5 C 0.3243(14) 0.8844(13) 0.1916(8) 0.052(4) Uani 1 1 d DU . . H3 H 0.3743 1.0191 0.2204 0.062 Uiso 1 1 calc R . . C6 C 0.1189(14) 0.7269(13) 0.1997(7) 0.051(4) Uani 1 1 d DU . . H4 H 0.0328 0.7487 0.2337 0.061 Uiso 1 1 calc R . . C7 C 0.0459(16) 0.5304(14) 0.1537(14) 0.052(4) Uani 1 1 d DU . . H5 H -0.0943 0.4227 0.1571 0.062 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 0.067(4) 0.061(3) 0.058(13) -0.018(6) 0.030(7) -0.004(3) O2 0.057(3) 0.055(3) 0.058(13) 0.002(6) 0.006(6) -0.016(2) C1 0.043(4) 0.041(3) 0.043(12) -0.005(7) 0.021(8) 0.009(3) C2 0.044(4) 0.035(3) 0.042(11) 0.017(7) -0.001(7) 0.006(3) C3 0.043(4) 0.055(4) 0.051(12) 0.007(8) 0.000(7) 0.006(3) C4 0.036(4) 0.048(3) 0.045(12) -0.002(7) -0.002(7) 0.001(3) C5 0.055(4) 0.046(3) 0.052(12) 0.001(7) 0.002(8) 0.007(3) C6 0.051(4) 0.049(4) 0.052(12) 0.002(7) 0.008(8) -0.004(3) C7 0.053(4) 0.048(4) 0.052(12) 0.007(8) 0.002(8) -0.002(3) _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 C1 1.24(2) . ? O1 H6A 0.8200 . ? O2 C1 1.309(8) . ? O2 H6 0.8200 . ? C1 C2 1.47(3) . ? C2 C3 1.383(10) . ? C2 C7 1.41(4) . ? C3 C4 1.30(2) . ? C3 H1 0.9300 . ? C4 C5 1.39(3) . ? C4 H2 0.9300 . ? C5 C6 1.377(9) . ? C5 H3 0.9300 . ? C6 C7 1.41(3) . ? C6 H4 0.9300 . ? C7 H5 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H6A 109.5 . . ? C1 O2 H6 109.5 . . ? O1 C1 O2 125.7(15) . . ? O1 C1 C2 119.9(8) . . ? O2 C1 C2 114.3(16) . . ? C3 C2 C1 124.7(18) . . ? C3 C2 C7 114.2(19) . . ? C1 C2 C7 121.0(9) . . ? C4 C3 C2 127.0(16) . . ? C4 C3 H1 116.5 . . ? C2 C3 H1 116.5 . . ? C3 C4 C5 117.4(9) . . ? C3 C4 H2 121.3 . . ? C5 C4 H2 121.3 . . ? C6 C5 C4 122.7(12) . . ? C6 C5 H3 118.7 . . ? C4 C5 H3 118.7 . . ? C7 C6 C5 116.5(13) . . ? C7 C6 H4 121.8 . . ? C5 C6 H4 121.8 . . ? C6 C7 C2 122.1(8) . . ? C6 C7 H5 119.0 . . ? C2 C7 H5 119.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -1(3) . . . . ? O2 C1 C2 C3 178.4(15) . . . . ? O1 C1 C2 C7 -176.7(16) . . . . ? O2 C1 C2 C7 3(2) . . . . ? C1 C2 C3 C4 177.6(16) . . . . ? C7 C2 C3 C4 -6(3) . . . . ? C2 C3 C4 C5 6(2) . . . . ? C3 C4 C5 C6 -2(2) . . . . ? C4 C5 C6 C7 -1.8(18) . . . . ? C5 C6 C7 C2 1(2) . . . . ? C3 C2 C7 C6 2(3) . . . . ? C1 C2 C7 C6 178.4(12) . . . . ? _diffrn_measured_fraction_theta_max 0.141 _diffrn_reflns_theta_full 28.41 _diffrn_measured_fraction_theta_full 0.141 _refine_diff_density_max 0.086 _refine_diff_density_min -0.089 _refine_diff_density_rms 0.021 #++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ data_benziocacid_0.42GPa(CCDC864019) _database_code_depnum_ccdc_archive 'CCDC 864019' #TrackingRef '- All BA cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'benzioc acid' _chemical_melting_point ? _chemical_formula_moiety 'C7 H6 O2' _chemical_formula_sum 'C7 H6 O2' _chemical_formula_weight 122.12 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-p 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.3454(15) _cell_length_b 5.0400(16) _cell_length_c 21.688(17) _cell_angle_alpha 90.00 _cell_angle_beta 98.36(8) _cell_angle_gamma 90.00 _cell_volume 578.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_pressure 420000 _cell_measurement_reflns_used 1945 _cell_measurement_theta_min 4.15 _cell_measurement_theta_max 28.14 _exptl_crystal_description plate-shaped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.515 _exptl_absorpt_correction_T_max 0.932 _exptl_absorpt_process_details ; Katrusiak, A. (2003). REDSHABS - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Pozna\'n. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 ; _exptl_special_details ; Data were collected at room temperature and pressure of 0.42(3) GPa (420000 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 296(2) _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 'Kuma KM4CCD \k geometry' _diffrn_measurement_method ;HP omega scans - for more details see: A. Budzianowski, A. Katrusiak in High-Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168 ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1945 _diffrn_reflns_av_R_equivalents 0.2304 _diffrn_reflns_av_sigmaI/netI 0.1092 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 4.15 _diffrn_reflns_theta_max 28.14 _reflns_number_total 170 _reflns_number_gt 149 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2004)' _computing_cell_refinement 'CrysAlis (Oxford Diffraction, 2004)' _computing_data_reduction 'CrysAlisRED (Oxford Diffraction, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury (Macrae et al., 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0756P)^2^+0.8252P] 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_number_reflns 170 _refine_ls_number_parameters 82 _refine_ls_number_restraints 132 _refine_ls_R_factor_all 0.1250 _refine_ls_R_factor_gt 0.0999 _refine_ls_wR_factor_ref 0.2153 _refine_ls_wR_factor_gt 0.1986 _refine_ls_goodness_of_fit_ref 1.314 _refine_ls_restrained_S_all 0.906 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2244(12) 0.2437(10) 0.0142(8) 0.058(4) Uani 1 1 d DU . . H6A H 0.1645 0.1193 -0.0075 0.087 Uiso 0.80(13) 1 calc PR . . O2 O -0.0985(10) 0.1437(9) 0.0659(8) 0.056(4) Uani 1 1 d DU . . H6 H -0.1209 0.0303 0.0385 0.084 Uiso 0.20(13) 1 calc PR . . C1 C 0.0963(15) 0.2780(13) 0.0598(11) 0.045(4) Uani 1 1 d DU . . C2 C 0.1789(14) 0.4893(13) 0.1021(14) 0.041(3) Uani 1 1 d U . . C3 C 0.3870(16) 0.6459(13) 0.1007(14) 0.046(4) Uani 1 1 d U . . H1 H 0.4840 0.6198 0.0690 0.055 Uiso 1 1 calc R . . C4 C 0.4592(18) 0.8399(15) 0.1441(16) 0.050(4) Uani 1 1 d U . . H2 H 0.6000 0.9446 0.1409 0.061 Uiso 1 1 calc R . . C5 C 0.3287(15) 0.8768(14) 0.1901(8) 0.053(4) Uani 1 1 d DU . . H3 H 0.3781 1.0110 0.2187 0.064 Uiso 1 1 calc R . . C6 C 0.1203(19) 0.7241(14) 0.1977(15) 0.056(4) Uani 1 1 d U . . H4 H 0.0314 0.7508 0.2310 0.067 Uiso 1 1 calc R . . C7 C 0.0499(16) 0.5273(14) 0.1529(13) 0.046(3) Uani 1 1 d U . . H5 H -0.0872 0.4186 0.1572 0.055 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 0.071(4) 0.052(3) 0.052(10) -0.012(6) 0.013(6) -0.012(3) O2 0.056(3) 0.052(3) 0.062(11) -0.001(6) 0.012(6) -0.015(2) C1 0.050(5) 0.039(3) 0.044(9) 0.001(6) 0.002(7) 0.003(3) C2 0.040(4) 0.036(3) 0.046(8) -0.002(5) 0.004(6) 0.011(2) C3 0.045(4) 0.044(3) 0.048(9) 0.001(6) 0.002(6) 0.003(3) C4 0.042(4) 0.052(4) 0.054(10) -0.004(6) -0.004(6) -0.002(3) C5 0.062(5) 0.042(3) 0.054(9) -0.001(6) 0.003(7) 0.007(3) C6 0.062(5) 0.053(4) 0.053(9) -0.011(6) 0.011(7) 0.007(3) C7 0.056(4) 0.036(3) 0.046(9) 0.002(6) 0.007(6) 0.012(3) _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 C1 1.294(19) . ? O1 H6A 0.8200 . ? O2 C1 1.265(6) . ? O2 H6 0.8200 . ? C1 C2 1.43(3) . ? C2 C7 1.40(4) . ? C2 C3 1.368(10) . ? C3 C4 1.37(3) . ? C3 H1 0.9300 . ? C4 C5 1.31(3) . ? C4 H2 0.9300 . ? C5 C6 1.383(11) . ? C5 H3 0.9300 . ? C6 C7 1.40(3) . ? C6 H4 0.9300 . ? C7 H5 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H6A 109.5 . . ? C1 O2 H6 109.5 . . ? O2 C1 O1 122.9(14) . . ? O2 C1 C2 120.8(16) . . ? O1 C1 C2 116.2(9) . . ? C7 C2 C3 116(2) . . ? C7 C2 C1 117.8(9) . . ? C3 C2 C1 126(2) . . ? C2 C3 C4 123.0(19) . . ? C2 C3 H1 118.5 . . ? C4 C3 H1 118.5 . . ? C5 C4 C3 119.6(10) . . ? C5 C4 H2 120.2 . . ? C3 C4 H2 120.2 . . ? C4 C5 C6 122.6(17) . . ? C4 C5 H3 118.7 . . ? C6 C5 H3 118.7 . . ? C7 C6 C5 116.8(19) . . ? C7 C6 H4 121.6 . . ? C5 C6 H4 121.6 . . ? C6 C7 C2 122.1(10) . . ? C6 C7 H5 119.0 . . ? C2 C7 H5 119.0 . . ? 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 O2 C1 C2 C7 5(3) . . . . ? O1 C1 C2 C7 -178.2(15) . . . . ? O2 C1 C2 C3 179.3(16) . . . . ? O1 C1 C2 C3 -4(3) . . . . ? C7 C2 C3 C4 -4(3) . . . . ? C1 C2 C3 C4 -177.9(18) . . . . ? C2 C3 C4 C5 1(3) . . . . ? C3 C4 C5 C6 1(3) . . . . ? C4 C5 C6 C7 -1(3) . . . . ? C5 C6 C7 C2 -1(3) . . . . ? C3 C2 C7 C6 4(3) . . . . ? C1 C2 C7 C6 178.4(14) . . . . ? _diffrn_measured_fraction_theta_max 0.120 _diffrn_reflns_theta_full 28.14 _diffrn_measured_fraction_theta_full 0.120 _refine_diff_density_max 0.065 _refine_diff_density_min -0.064 _refine_diff_density_rms 0.019 data_benziocacid_0.21GPa(CCDC864020) _database_code_depnum_ccdc_archive 'CCDC 864020' #TrackingRef '- All BA cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'benzioc acid' _chemical_melting_point ? _chemical_formula_moiety 'C7 H6 O2' _chemical_formula_sum 'C7 H6 O2' _chemical_formula_weight 122.12 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-p 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.402(4) _cell_length_b 5.067(3) _cell_length_c 21.751(15) _cell_angle_alpha 90.00 _cell_angle_beta 98.10(6) _cell_angle_gamma 90.00 _cell_volume 589.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_pressure 210000 _cell_measurement_reflns_used 1939 _cell_measurement_theta_min 5.72 _cell_measurement_theta_max 27.98 _exptl_crystal_description plate-shaped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.495 _exptl_absorpt_correction_T_max 0.916 _exptl_absorpt_process_details ; Katrusiak, A. (2003). REDSHABS - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Pozna\'n. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 ; _exptl_special_details ; Data were collected at room temperature and pressure of 0.21(3) GPa (210000 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 296(2) _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 "'Oxford Diffraction Xcalibur Eos" _diffrn_measurement_method ;HP omega scans - for more details see: A. Budzianowski, A. Katrusiak in High-Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168 ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1939 _diffrn_reflns_av_R_equivalents 0.1626 _diffrn_reflns_av_sigmaI/netI 0.0866 _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 -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 5.72 _diffrn_reflns_theta_max 27.98 _reflns_number_total 218 _reflns_number_gt 170 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2004)' _computing_cell_refinement 'CrysAlis (Oxford Diffraction, 2004)' _computing_data_reduction 'CrysAlisRED (Oxford Diffraction, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury (Macrae et al., 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0162P] 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_number_reflns 218 _refine_ls_number_parameters 72 _refine_ls_number_restraints 63 _refine_ls_R_factor_all 0.1365 _refine_ls_R_factor_gt 0.0875 _refine_ls_wR_factor_ref 0.0847 _refine_ls_wR_factor_gt 0.0767 _refine_ls_goodness_of_fit_ref 1.477 _refine_ls_restrained_S_all 1.293 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.225(2) 0.2425(14) 0.0155(7) 0.070(6) Uani 1 1 d DU . . H6A H 0.1689 0.1197 -0.0068 0.105 Uiso 0.86(12) 1 calc PR . . O2 O -0.1020(13) 0.1420(6) 0.0666(4) 0.073(5) Uani 1 1 d DU . . H6 H -0.1294 0.0370 0.0378 0.110 Uiso 0.14(12) 1 calc PR . . C1 C 0.086(3) 0.276(2) 0.0605(8) 0.067(7) Uani 1 1 d DU . . C2 C 0.178(3) 0.4791(17) 0.1060(10) 0.053(3) Uiso 1 1 d . . . C3 C 0.382(3) 0.6373(8) 0.0996(10) 0.062(5) Uani 1 1 d U . . H1 H 0.4698 0.6135 0.0662 0.074 Uiso 1 1 calc R . . C4 C 0.456(3) 0.837(2) 0.1446(8) 0.069(7) Uani 1 1 d U . . H2 H 0.5908 0.9464 0.1411 0.082 Uiso 1 1 calc R . . C5 C 0.329(3) 0.861(2) 0.1904(11) 0.054(6) Uani 1 1 d U . . H3 H 0.3820 0.9862 0.2207 0.065 Uiso 1 1 calc R . . C6 C 0.122(3) 0.7127(10) 0.1970(9) 0.071(2) Uiso 1 1 d . . . H4 H 0.0295 0.7327 0.2296 0.085 Uiso 1 1 calc R . . C7 C 0.064(3) 0.5214(14) 0.1476(10) 0.045(6) Uani 1 1 d U . . H5 H -0.0797 0.4207 0.1486 0.054 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 0.082(9) 0.058(3) 0.072(11) -0.008(6) 0.018(7) -0.016(5) O2 0.085(7) 0.069(2) 0.065(10) -0.007(4) 0.006(7) -0.012(4) C1 0.062(10) 0.072(6) 0.067(11) 0.007(7) 0.005(8) 0.018(6) C3 0.065(8) 0.061(2) 0.059(10) 0.007(6) 0.007(7) -0.001(5) C4 0.067(10) 0.074(5) 0.063(11) -0.003(7) 0.003(8) 0.003(6) C5 0.052(9) 0.054(4) 0.057(11) 0.000(7) 0.012(8) -0.002(6) C7 0.052(9) 0.040(3) 0.043(11) 0.001(6) 0.009(8) -0.007(5) _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 C1 1.32(2) . ? O1 H6A 0.8200 . ? O2 C1 1.244(15) . ? O2 H6 0.8200 . ? C1 C2 1.466(16) . ? C2 C7 1.19(5) . ? C2 C3 1.38(2) . ? C3 C4 1.42(2) . ? C3 H1 0.9300 . ? C4 C5 1.29(4) . ? C4 H2 0.9300 . ? C5 C6 1.37(2) . ? C5 H3 0.9300 . ? C6 C7 1.45(2) . ? C6 H4 0.9300 . ? C7 H5 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H6A 109.5 . . ? C1 O2 H6 109.5 . . ? O2 C1 O1 124.4(14) . . ? O2 C1 C2 120.9(18) . . ? O1 C1 C2 114.5(17) . . ? C7 C2 C3 118.6(13) . . ? C7 C2 C1 119(2) . . ? C3 C2 C1 123(2) . . ? C2 C3 C4 119(2) . . ? C2 C3 H1 120.3 . . ? C4 C3 H1 120.3 . . ? C5 C4 C3 118.2(17) . . ? C5 C4 H2 120.9 . . ? C3 C4 H2 120.9 . . ? C4 C5 C6 123.7(15) . . ? C4 C5 H3 118.1 . . ? C6 C5 H3 118.1 . . ? C5 C6 C7 113(2) . . ? C5 C6 H4 123.7 . . ? C7 C6 H4 123.7 . . ? C2 C7 C6 127(2) . . ? C2 C7 H5 116.4 . . ? C6 C7 H5 116.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C7 -2.9(17) . . . . ? O1 C1 C2 C7 179.7(12) . . . . ? O2 C1 C2 C3 -177.9(8) . . . . ? O1 C1 C2 C3 4.8(15) . . . . ? C7 C2 C3 C4 3.1(14) . . . . ? C1 C2 C3 C4 178.0(8) . . . . ? C2 C3 C4 C5 0.6(15) . . . . ? C3 C4 C5 C6 -2.7(19) . . . . ? C4 C5 C6 C7 1.3(15) . . . . ? C3 C2 C7 C6 -4.9(18) . . . . ? C1 C2 C7 C6 180.0(6) . . . . ? C5 C6 C7 C2 2.8(14) . . . . ? _diffrn_measured_fraction_theta_max 0.153 _diffrn_reflns_theta_full 27.98 _diffrn_measured_fraction_theta_full 0.153 _refine_diff_density_max 0.034 _refine_diff_density_min -0.031 _refine_diff_density_rms 0.009 #++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ data_benziocacid_1.96GPa(CCDC864021) _database_code_depnum_ccdc_archive 'CCDC 864021' #TrackingRef '- All BA cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'benzioc acid' _chemical_melting_point ? _chemical_formula_moiety 'C7 H6 O2' _chemical_formula_sum 'C7 H6 O2' _chemical_formula_weight 122.12 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-p 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.1036(11) _cell_length_b 4.8981(10) _cell_length_c 21.176(16) _cell_angle_alpha 90.00 _cell_angle_beta 100.38(6) _cell_angle_gamma 90.00 _cell_volume 520.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_pressure 1960000 _cell_measurement_reflns_used 2032 _cell_measurement_theta_min 4.27 _cell_measurement_theta_max 29.18 _exptl_crystal_description plate-shaped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.558 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.443 _exptl_absorpt_correction_T_max 0.923 _exptl_absorpt_process_details ; Katrusiak, A. (2003). REDSHABS - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Pozna\'n. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 ; _exptl_special_details ; Data were collected at room temperature and pressure of 1.96(3) GPa (1960000 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 296(2) _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 'Kuma KM4CCD \k geometry' _diffrn_measurement_method ;HP omega scans - for more details see: A. Budzianowski, A. Katrusiak in High-Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168 ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2032 _diffrn_reflns_av_R_equivalents 0.2626 _diffrn_reflns_av_sigmaI/netI 0.1048 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.27 _diffrn_reflns_theta_max 29.18 _reflns_number_total 214 _reflns_number_gt 160 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2004)' _computing_cell_refinement 'CrysAlis (Oxford Diffraction, 2004)' _computing_data_reduction 'CrysAlisRED (Oxford Diffraction, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury (Macrae et al., 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.1095P] 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_number_reflns 214 _refine_ls_number_parameters 82 _refine_ls_number_restraints 76 _refine_ls_R_factor_all 0.1128 _refine_ls_R_factor_gt 0.0765 _refine_ls_wR_factor_ref 0.1048 _refine_ls_wR_factor_gt 0.0919 _refine_ls_goodness_of_fit_ref 1.301 _refine_ls_restrained_S_all 1.158 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2307(8) 0.2485(6) 0.0131(6) 0.055(4) Uani 1 1 d U . . H6A H 0.1658 0.1192 -0.0089 0.082 Uiso 0.57(9) 1 calc PR . . O2 O -0.1120(6) 0.1487(6) 0.0620(5) 0.053(4) Uani 1 1 d U . . H6 H -0.1352 0.0321 0.0337 0.080 Uiso 0.43(9) 1 calc PR . . C1 C 0.0952(12) 0.2951(10) 0.0566(9) 0.045(4) Uani 1 1 d U . . C2 C 0.1795(11) 0.5086(10) 0.1041(10) 0.045(3) Uani 1 1 d U . . C3 C 0.3910(11) 0.6779(10) 0.1009(9) 0.052(4) Uani 1 1 d U . . H1 H 0.4899 0.6516 0.0686 0.062 Uiso 1 1 calc R . . C4 C 0.4594(13) 0.8829(9) 0.1439(10) 0.045(4) Uani 1 1 d U . . H2 H 0.5950 1.0031 0.1388 0.054 Uiso 1 1 calc R . . C5 C 0.3266(10) 0.9142(9) 0.1960(8) 0.049(4) Uani 1 1 d U . . H3 H 0.3801 1.0516 0.2258 0.059 Uiso 1 1 calc R . . C6 C 0.1188(14) 0.7458(9) 0.2037(8) 0.052(4) Uani 1 1 d DU . . H4 H 0.0336 0.7622 0.2389 0.063 Uiso 1 1 calc R . . C7 C 0.0401(11) 0.5438(9) 0.1550(9) 0.045(4) Uani 1 1 d DU . . H5 H -0.1064 0.4336 0.1571 0.054 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 0.068(3) 0.049(2) 0.048(11) -0.001(4) 0.012(6) -0.0037(18) O2 0.047(3) 0.053(2) 0.056(12) -0.011(5) 0.000(5) -0.0112(18) C1 0.050(4) 0.041(3) 0.046(11) 0.009(5) 0.011(6) 0.010(2) C2 0.047(3) 0.035(2) 0.052(10) -0.002(5) 0.007(6) 0.000(2) C3 0.055(4) 0.047(2) 0.054(11) -0.004(6) 0.014(6) -0.003(3) C4 0.039(3) 0.047(2) 0.047(11) 0.002(6) 0.001(6) -0.005(2) C5 0.048(4) 0.050(3) 0.049(11) -0.002(5) 0.008(7) 0.008(2) C6 0.063(4) 0.044(3) 0.053(11) -0.002(5) 0.019(7) -0.003(2) C7 0.044(3) 0.043(3) 0.044(10) 0.004(5) -0.002(6) 0.012(2) _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 C1 1.270(16) . ? O1 H6A 0.8200 . ? O2 C1 1.299(6) . ? O2 H6 0.8200 . ? C1 C2 1.460(17) . ? C2 C3 1.372(7) . ? C2 C7 1.40(2) . ? C3 C4 1.358(15) . ? C3 H1 0.9300 . ? C4 C5 1.40(2) . ? C4 H2 0.9300 . ? C5 C6 1.377(6) . ? C5 H3 0.9300 . ? C6 C7 1.434(19) . ? C6 H4 0.9300 . ? C7 H5 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H6A 109.5 . . ? C1 O2 H6 109.5 . . ? O1 C1 O2 121.5(10) . . ? O1 C1 C2 119.8(6) . . ? O2 C1 C2 118.6(11) . . ? C3 C2 C7 118.3(13) . . ? C3 C2 C1 122.4(14) . . ? C7 C2 C1 119.2(6) . . ? C2 C3 C4 121.6(13) . . ? C2 C3 H1 119.2 . . ? C4 C3 H1 119.2 . . ? C3 C4 C5 120.4(6) . . ? C3 C4 H2 119.8 . . ? C5 C4 H2 119.8 . . ? C6 C5 C4 121.4(11) . . ? C6 C5 H3 119.3 . . ? C4 C5 H3 119.3 . . ? C5 C6 C7 116.7(12) . . ? C5 C6 H4 121.7 . . ? C7 C6 H4 121.7 . . ? C6 C7 C2 121.5(6) . . ? C6 C7 H5 119.3 . . ? C2 C7 H5 119.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 5.0(18) . . . . ? O2 C1 C2 C3 -178.0(9) . . . . ? O1 C1 C2 C7 -175.1(11) . . . . ? O2 C1 C2 C7 2.0(16) . . . . ? C7 C2 C3 C4 -2.8(17) . . . . ? C1 C2 C3 C4 177.1(9) . . . . ? C2 C3 C4 C5 4.8(17) . . . . ? C3 C4 C5 C6 -2.3(17) . . . . ? C4 C5 C6 C7 -2.0(16) . . . . ? C5 C6 C7 C2 3.9(15) . . . . ? C3 C2 C7 C6 -1.6(16) . . . . ? C1 C2 C7 C6 178.4(10) . . . . ? _diffrn_measured_fraction_theta_max 0.153 _diffrn_reflns_theta_full 29.18 _diffrn_measured_fraction_theta_full 0.153 _refine_diff_density_max 0.053 _refine_diff_density_min -0.068 _refine_diff_density_rms 0.017 #+++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ data_benziocacid1.48GPa(CCDC864022) _database_code_depnum_ccdc_archive 'CCDC 864022' #TrackingRef '- All BA cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'benzioc acid' _chemical_melting_point ? _chemical_formula_moiety 'C7 H6 O2' _chemical_formula_sum 'C7 H6 O2' _chemical_formula_weight 122.12 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-p 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.1578(11) _cell_length_b 4.9334(11) _cell_length_c 21.302(15) _cell_angle_alpha 90.00 _cell_angle_beta 99.82(6) _cell_angle_gamma 90.00 _cell_volume 534.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_pressure 1480000 _cell_measurement_reflns_used 2128 _cell_measurement_theta_min 4.15 _cell_measurement_theta_max 28.63 _exptl_crystal_description plate-shaped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.482 _exptl_absorpt_correction_T_max 0.927 _exptl_absorpt_process_details ; Katrusiak, A. (2003). REDSHABS - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Pozna\'n. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 ; _exptl_special_details ; Data were collected at room temperature and pressure of 1.48(3) GPa (1480000 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 296(2) _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 'Kuma KM4CCD \k geometry' _diffrn_measurement_method ;HP omega scans - for more details see: A. Budzianowski, A. Katrusiak in High-Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168 ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2128 _diffrn_reflns_av_R_equivalents 0.1591 _diffrn_reflns_av_sigmaI/netI 0.0624 _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 -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 4.15 _diffrn_reflns_theta_max 28.63 _reflns_number_total 202 _reflns_number_gt 167 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2004)' _computing_cell_refinement 'CrysAlis (Oxford Diffraction, 2004)' _computing_data_reduction 'CrysAlisRED (Oxford Diffraction, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury (Macrae et al., 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.2671P] 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_number_reflns 202 _refine_ls_number_parameters 82 _refine_ls_number_restraints 76 _refine_ls_R_factor_all 0.0886 _refine_ls_R_factor_gt 0.0667 _refine_ls_wR_factor_ref 0.1053 _refine_ls_wR_factor_gt 0.0990 _refine_ls_goodness_of_fit_ref 1.353 _refine_ls_restrained_S_all 1.178 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2307(9) 0.2473(7) 0.0142(7) 0.052(4) Uani 1 1 d DU . . H6A H 0.1679 0.1192 -0.0078 0.078 Uiso 0.63(10) 1 calc PR . . O2 O -0.1085(8) 0.1492(6) 0.0638(6) 0.053(4) Uani 1 1 d U . . H6 H -0.1420 0.0398 0.0346 0.079 Uiso 0.37(10) 1 calc PR . . C1 C 0.0956(12) 0.2918(10) 0.0563(10) 0.041(4) Uani 1 1 d U . . C2 C 0.1785(10) 0.5010(10) 0.1055(9) 0.038(3) Uani 1 1 d U . . C3 C 0.3912(11) 0.6707(10) 0.1026(11) 0.043(4) Uani 1 1 d U . . H1 H 0.4893 0.6431 0.0703 0.052 Uiso 1 1 calc R . . C4 C 0.4610(12) 0.8726(9) 0.1442(11) 0.040(4) Uani 1 1 d U . . H2 H 0.5984 0.9884 0.1393 0.049 Uiso 1 1 calc R . . C5 C 0.3241(12) 0.9068(9) 0.1952(10) 0.045(4) Uani 1 1 d U . . H3 H 0.3744 1.0433 0.2249 0.054 Uiso 1 1 calc R . . C6 C 0.1167(12) 0.7407(9) 0.2018(9) 0.041(4) Uani 1 1 d DU . . H4 H 0.0279 0.7606 0.2360 0.049 Uiso 1 1 calc R . . C7 C 0.0426(11) 0.5410(10) 0.1556(10) 0.044(4) Uani 1 1 d U . . H5 H -0.1019 0.4320 0.1586 0.053 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 0.059(3) 0.050(2) 0.049(11) -0.009(5) 0.015(6) -0.0024(17) O2 0.048(3) 0.051(2) 0.060(13) -0.010(5) 0.012(5) -0.0123(17) C1 0.043(4) 0.039(3) 0.042(11) 0.008(6) 0.009(7) 0.008(2) C2 0.038(3) 0.033(2) 0.042(10) 0.003(6) 0.006(6) 0.004(2) C3 0.039(3) 0.046(3) 0.044(11) 0.001(6) 0.006(6) 0.003(2) C4 0.035(3) 0.044(2) 0.040(11) 0.001(6) 0.000(6) -0.010(2) C5 0.046(3) 0.047(3) 0.044(11) 0.010(6) 0.012(7) 0.007(2) C6 0.051(3) 0.037(3) 0.039(11) 0.010(6) 0.019(6) 0.005(2) C7 0.047(3) 0.041(3) 0.045(11) 0.006(6) 0.010(7) 0.003(2) _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 C1 1.245(18) . ? O1 H6A 0.8200 . ? O2 C1 1.299(6) . ? O2 H6 0.8200 . ? C1 C2 1.48(2) . ? C2 C7 1.39(2) . ? C2 C3 1.390(7) . ? C3 C4 1.342(19) . ? C3 H1 0.9300 . ? C4 C5 1.40(2) . ? C4 H2 0.9300 . ? C5 C6 1.373(7) . ? C5 H3 0.9300 . ? C6 C7 1.40(2) . ? C6 H4 0.9300 . ? C7 H5 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H6A 109.5 . . ? C1 O2 H6 109.5 . . ? O1 C1 O2 123.9(12) . . ? O1 C1 C2 120.2(6) . . ? O2 C1 C2 115.6(14) . . ? C7 C2 C3 117.1(13) . . ? C7 C2 C1 121.4(6) . . ? C3 C2 C1 121.5(14) . . ? C4 C3 C2 122.8(14) . . ? C4 C3 H1 118.6 . . ? C2 C3 H1 118.6 . . ? C3 C4 C5 119.2(7) . . ? C3 C4 H2 120.4 . . ? C5 C4 H2 120.4 . . ? C6 C5 C4 120.7(13) . . ? C6 C5 H3 119.7 . . ? C4 C5 H3 119.7 . . ? C7 C6 C5 118.3(13) . . ? C7 C6 H4 120.9 . . ? C5 C6 H4 120.9 . . ? C2 C7 C6 121.8(6) . . ? C2 C7 H5 119.1 . . ? C6 C7 H5 119.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C7 -175.2(12) . . . . ? O2 C1 C2 C7 -0.8(18) . . . . ? O1 C1 C2 C3 6.7(18) . . . . ? O2 C1 C2 C3 -178.9(9) . . . . ? C7 C2 C3 C4 -2.4(19) . . . . ? C1 C2 C3 C4 175.8(11) . . . . ? C2 C3 C4 C5 4(2) . . . . ? C3 C4 C5 C6 -1.7(19) . . . . ? C4 C5 C6 C7 -1.3(18) . . . . ? C3 C2 C7 C6 -0.8(19) . . . . ? C1 C2 C7 C6 -179.0(9) . . . . ? C5 C6 C7 C2 2.5(19) . . . . ? _diffrn_measured_fraction_theta_max 0.148 _diffrn_reflns_theta_full 28.63 _diffrn_measured_fraction_theta_full 0.148 _refine_diff_density_max 0.079 _refine_diff_density_min -0.069 _refine_diff_density_rms 0.018 #++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ data_benziocacid_1.12GPa(CCDC864023) _database_code_depnum_ccdc_archive 'CCDC 864023' #TrackingRef '- All BA cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'benzioc acid' _chemical_melting_point ? _chemical_formula_moiety 'C7 H6 O2' _chemical_formula_sum 'C7 H6 O2' _chemical_formula_weight 122.12 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-p 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.2086(10) _cell_length_b 4.9633(11) _cell_length_c 21.468(15) _cell_angle_alpha 90.00 _cell_angle_beta 99.48(6) _cell_angle_gamma 90.00 _cell_volume 547.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_pressure 1120000 _cell_measurement_reflns_used 2058 _cell_measurement_theta_min 3.97 _cell_measurement_theta_max 28.43 _exptl_crystal_description plate-shaped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.482 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.456 _exptl_absorpt_correction_T_max 0.923 _exptl_absorpt_process_details ; Katrusiak, A. (2003). REDSHABS - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Pozna\'n. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 ; _exptl_special_details ; Data were collected at room temperature and pressure of 1.12(3) GPa (1120000 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 296(2) _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 'Kuma KM4CCD \k geometry' _diffrn_measurement_method ;HP omega scans - for more details see: A. Budzianowski, A. Katrusiak in High-Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168 ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2058 _diffrn_reflns_av_R_equivalents 0.1640 _diffrn_reflns_av_sigmaI/netI 0.0670 _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 -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.97 _diffrn_reflns_theta_max 28.43 _reflns_number_total 189 _reflns_number_gt 143 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2004)' _computing_cell_refinement 'CrysAlis (Oxford Diffraction, 2004)' _computing_data_reduction 'CrysAlisRED (Oxford Diffraction, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury (Macrae et al., 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1102P)^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_number_reflns 189 _refine_ls_number_parameters 82 _refine_ls_number_restraints 78 _refine_ls_R_factor_all 0.0716 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1503 _refine_ls_wR_factor_gt 0.1324 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 0.983 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2284(8) 0.2435(7) 0.0140(6) 0.061(4) Uani 1 1 d DU . . H6A H 0.1668 0.1137 -0.0069 0.091 Uiso 0.71(9) 1 calc PR . . O2 O -0.1057(7) 0.1508(7) 0.0650(6) 0.055(4) Uani 1 1 d DU . . H6 H -0.1374 0.0387 0.0367 0.083 Uiso 0.29(9) 1 calc PR . . C1 C 0.0982(11) 0.2880(9) 0.0574(7) 0.042(4) Uani 1 1 d DU . . C2 C 0.1788(10) 0.4970(9) 0.1042(9) 0.042(4) Uani 1 1 d U . . C3 C 0.3885(11) 0.6644(9) 0.1007(10) 0.047(4) Uani 1 1 d U . . H1 H 0.4838 0.6385 0.0681 0.056 Uiso 1 1 calc R . . C4 C 0.4594(12) 0.8626(9) 0.1425(10) 0.044(4) Uani 1 1 d U . . H2 H 0.5968 0.9762 0.1377 0.053 Uiso 1 1 calc R . . C5 C 0.3239(11) 0.8975(8) 0.1937(8) 0.050(4) Uani 1 1 d DU . . H3 H 0.3752 1.0335 0.2229 0.060 Uiso 1 1 calc R . . C6 C 0.1175(11) 0.7345(8) 0.2014(10) 0.046(4) Uani 1 1 d U . . H4 H 0.0312 0.7552 0.2358 0.055 Uiso 1 1 calc R . . C7 C 0.0426(11) 0.5362(9) 0.1555(9) 0.046(4) Uani 1 1 d U . . H5 H -0.1000 0.4276 0.1588 0.056 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 0.068(3) 0.056(2) 0.064(11) -0.013(5) 0.025(6) -0.0028(18) O2 0.057(3) 0.054(2) 0.059(13) -0.011(5) 0.020(5) -0.0127(16) C1 0.045(3) 0.037(2) 0.041(11) 0.009(6) 0.002(7) 0.010(2) C2 0.048(3) 0.036(2) 0.043(10) 0.006(6) 0.008(6) 0.006(2) C3 0.043(3) 0.048(2) 0.050(12) -0.005(6) 0.007(7) -0.001(2) C4 0.040(3) 0.045(2) 0.044(11) 0.004(6) -0.004(6) -0.007(2) C5 0.055(4) 0.048(2) 0.047(11) 0.011(6) 0.009(7) 0.010(2) C6 0.052(4) 0.045(3) 0.043(11) 0.008(6) 0.009(7) 0.002(2) C7 0.054(4) 0.040(3) 0.045(11) 0.009(6) 0.010(7) 0.002(2) _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 C1 1.259(12) . ? O1 H6A 0.8200 . ? O2 C1 1.294(5) . ? O2 H6 0.8200 . ? C1 C2 1.456(19) . ? C2 C3 1.384(7) . ? C2 C7 1.42(2) . ? C3 C4 1.342(19) . ? C3 H1 0.9300 . ? C4 C5 1.41(2) . ? C4 H2 0.9300 . ? C5 C6 1.377(7) . ? C5 H3 0.9300 . ? C6 C7 1.40(2) . ? C6 H4 0.9300 . ? C7 H5 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H6A 109.5 . . ? C1 O2 H6 109.5 . . ? O1 C1 O2 123.6(9) . . ? O1 C1 C2 120.4(6) . . ? O2 C1 C2 116.0(11) . . ? C3 C2 C7 117.4(14) . . ? C3 C2 C1 122.1(14) . . ? C7 C2 C1 120.6(6) . . ? C4 C3 C2 122.4(14) . . ? C4 C3 H1 118.8 . . ? C2 C3 H1 118.8 . . ? C3 C4 C5 119.6(7) . . ? C3 C4 H2 120.2 . . ? C5 C4 H2 120.2 . . ? C6 C5 C4 121.5(12) . . ? C6 C5 H3 119.3 . . ? C4 C5 H3 119.3 . . ? C5 C6 C7 117.4(14) . . ? C5 C6 H4 121.3 . . ? C7 C6 H4 121.3 . . ? C6 C7 C2 121.7(6) . . ? C6 C7 H5 119.1 . . ? C2 C7 H5 119.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 4.2(17) . . . . ? O2 C1 C2 C3 -177.9(9) . . . . ? O1 C1 C2 C7 -175.9(10) . . . . ? O2 C1 C2 C7 2.0(18) . . . . ? C7 C2 C3 C4 -2.0(19) . . . . ? C1 C2 C3 C4 178.0(10) . . . . ? C2 C3 C4 C5 2.7(18) . . . . ? C3 C4 C5 C6 -0.9(17) . . . . ? C4 C5 C6 C7 -1.5(18) . . . . ? C5 C6 C7 C2 2.2(19) . . . . ? C3 C2 C7 C6 -1(2) . . . . ? C1 C2 C7 C6 179.5(9) . . . . ? _diffrn_measured_fraction_theta_max 0.137 _diffrn_reflns_theta_full 28.43 _diffrn_measured_fraction_theta_full 0.137 _refine_diff_density_max 0.055 _refine_diff_density_min -0.075 _refine_diff_density_rms 0.018 #++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ data_benziocacid_2.21GPa(CCDC864024) _database_code_depnum_ccdc_archive 'CCDC 864024' #TrackingRef '- All BA cif files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Benzioc acid' _chemical_melting_point ? _chemical_formula_moiety 'C7 H6 O2' _chemical_formula_sum 'C7 H6 O2' _chemical_formula_weight 122.12 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-p 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.077(14) _cell_length_b 4.893(9) _cell_length_c 21.10(6) _cell_angle_alpha 90.00 _cell_angle_beta 100.6(4) _cell_angle_gamma 90.00 _cell_volume 515(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_pressure 2210000 _cell_measurement_reflns_used 1349 _cell_measurement_theta_min 4.28 _cell_measurement_theta_max 27.14 _exptl_crystal_description plate-shaped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.574 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.609 _exptl_absorpt_correction_T_max 0.949 _exptl_absorpt_process_details ; Katrusiak, A. (2003). REDSHABS - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Pozna\'n. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 ; _exptl_special_details ; Data were collected at room temperature and pressure of 2.21(3) GPa (2210000 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 296(2) _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 'Kuma KM4CCD \k geometry' _diffrn_measurement_method ;HP omega scans - for more details see: A. Budzianowski, A. Katrusiak in High-Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168 ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1349 _diffrn_reflns_av_R_equivalents 0.3204 _diffrn_reflns_av_sigmaI/netI 0.2852 _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 4.28 _diffrn_reflns_theta_max 27.24 _reflns_number_total 162 _reflns_number_gt 93 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2004)' _computing_cell_refinement 'CrysAlis (Oxford Diffraction, 2004)' _computing_data_reduction 'CrysAlisRED (Oxford Diffraction, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury (Macrae et al., 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^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_number_reflns 162 _refine_ls_number_parameters 82 _refine_ls_number_restraints 135 _refine_ls_R_factor_all 0.2213 _refine_ls_R_factor_gt 0.0982 _refine_ls_wR_factor_ref 0.1479 _refine_ls_wR_factor_gt 0.1083 _refine_ls_goodness_of_fit_ref 1.269 _refine_ls_restrained_S_all 0.873 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.222(2) 0.2512(10) 0.0075(10) 0.031(3) Uani 1 1 d DU . . H6A H 0.1656 0.1140 -0.0129 0.047 Uiso 0.52(14) 1 calc PR . . O2 O -0.120(2) 0.1544(12) 0.0603(10) 0.029(4) Uani 1 1 d DU . . H6 H -0.1461 0.0375 0.0320 0.035 Uiso 0.48(14) 1 calc PR . . C1 C 0.099(4) 0.2803(16) 0.0578(17) 0.009(3) Uani 1 1 d U . . C2 C 0.174(4) 0.5177(18) 0.1031(16) 0.014(3) Uani 1 1 d U . . C3 C 0.400(3) 0.6729(16) 0.1034(11) 0.016(3) Uani 1 1 d U . . H1 H 0.5144 0.6282 0.0752 0.019 Uiso 1 1 calc R . . C4 C 0.461(4) 0.887(2) 0.1433(17) 0.030(4) Uani 1 1 d U . . H2 H 0.5820 1.0208 0.1361 0.037 Uiso 1 1 calc R . . C5 C 0.323(2) 0.899(2) 0.1993(9) 0.036(4) Uani 1 1 d DU . . H3 H 0.3928 1.0133 0.2335 0.043 Uiso 1 1 calc R . . C6 C 0.100(3) 0.7495(18) 0.2032(11) 0.019(4) Uani 1 1 d DU . . H4 H -0.0019 0.7791 0.2349 0.023 Uiso 1 1 calc R . . C7 C 0.037(3) 0.5488(17) 0.1558(13) 0.014(4) Uani 1 1 d DU . . H5 H -0.1024 0.4288 0.1588 0.017 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 0.037(5) 0.030(4) 0.027(7) -0.005(4) 0.005(5) -0.002(3) O2 0.026(5) 0.033(4) 0.028(7) -0.002(5) 0.004(5) -0.003(3) C1 0.011(5) 0.003(4) 0.012(6) 0.004(4) -0.001(5) -0.001(4) C2 0.015(5) 0.013(4) 0.015(6) 0.002(4) 0.003(5) 0.000(3) C3 0.014(5) 0.013(4) 0.019(7) 0.005(4) 0.001(5) -0.003(4) C4 0.037(6) 0.023(5) 0.029(7) 0.001(5) 0.000(5) -0.010(4) C5 0.038(6) 0.035(5) 0.033(7) -0.005(5) 0.001(5) -0.005(4) C6 0.020(5) 0.017(5) 0.020(7) -0.005(5) 0.001(5) 0.009(4) C7 0.013(5) 0.014(4) 0.016(7) -0.004(4) 0.006(5) 0.005(4) _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 C1 1.34(3) . ? O1 H6A 0.8200 . ? O2 C1 1.278(13) . ? O2 H6 0.8200 . ? C1 C2 1.51(3) . ? C2 C3 1.378(14) . ? C2 C7 1.42(3) . ? C3 C4 1.34(3) . ? C3 H1 0.9300 . ? C4 C5 1.48(3) . ? C4 H2 0.9300 . ? C5 C6 1.363(14) . ? C5 H3 0.9300 . ? C6 C7 1.40(3) . ? C6 H4 0.9300 . ? C7 H5 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H6A 109.5 . . ? C1 O2 H6 109.5 . . ? O2 C1 O1 121(3) . . ? O2 C1 C2 117.7(15) . . ? O1 C1 C2 119.1(10) . . ? C3 C2 C7 118(2) . . ? C3 C2 C1 122.6(14) . . ? C7 C2 C1 118.4(10) . . ? C4 C3 C2 121.8(13) . . ? C4 C3 H1 119.1 . . ? C2 C3 H1 119.1 . . ? C3 C4 C5 116.3(10) . . ? C3 C4 H2 121.8 . . ? C5 C4 H2 121.8 . . ? C6 C5 C4 123.1(17) . . ? C6 C5 H3 118.4 . . ? C4 C5 H3 118.4 . . ? C5 C6 C7 114.7(13) . . ? C5 C6 H4 122.6 . . ? C7 C6 H4 122.6 . . ? C2 C7 C6 123.6(11) . . ? C2 C7 H5 118.2 . . ? C6 C7 H5 118.2 . . ? 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 O2 C1 C2 C3 -178(2) . . . . ? O1 C1 C2 C3 -14(4) . . . . ? O2 C1 C2 C7 15(4) . . . . ? O1 C1 C2 C7 179(2) . . . . ? C7 C2 C3 C4 -14(3) . . . . ? C1 C2 C3 C4 179(3) . . . . ? C2 C3 C4 C5 18(3) . . . . ? C3 C4 C5 C6 -17(3) . . . . ? C4 C5 C6 C7 11(3) . . . . ? C3 C2 C7 C6 8(3) . . . . ? C1 C2 C7 C6 176(2) . . . . ? C5 C6 C7 C2 -7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.141 _diffrn_reflns_theta_full 27.24 _diffrn_measured_fraction_theta_full 0.141 _refine_diff_density_max 0.068 _refine_diff_density_min -0.075 _refine_diff_density_rms 0.022