# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Andrzej Katrusiak' _publ_contact_author_email KATRAN@AMU.EDU.PL _publ_section_title ; Molecular association in low-temperature and high-pressure polymorphs of 1,1,1,2-tetrachloroethane ; loop_ _publ_author_name 'Andrzej Katrusiak' 'Maciej Bujak' # Attachment '1112TCE_CIF_LT_HPall16.cif' data_1112TCE_195K _database_code_depnum_ccdc_archive 'CCDC 746844' #TrackingRef '1112TCE_CIF_LT_HPall16.cif' # CHEMICAL DATA _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,1,2-tetrachloroethane ; _chemical_name_common 1,1,1,2-tetrachloroethane _chemical_melting_point ? _chemical_formula_moiety 'C2 H2 Cl4' _chemical_formula_sum 'C2 H2 Cl4' _chemical_formula_weight 167.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.2760(8) _cell_length_b 5.59764(17) _cell_length_c 10.3599(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.912(4) _cell_angle_gamma 90.00 _cell_volume 1214.58(8) _cell_formula_units_Z 8 _cell_measurement_temperature 195.0(1) _cell_measurement_reflns_used 3399 _cell_measurement_theta_min 3.73 _cell_measurement_theta_max 26.27 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.836 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 1.802 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6139 _exptl_absorpt_correction_T_max 0.7145 _exptl_absorpt_process_details ; Correction for absorption was made using CrysAlisRED (Oxford Diffraction, 2007). ; _exptl_special_details ; Data were collected at ambient pressure (100 kPa) and 195 K with the crystal obtained by the in-situ low-temperature crystallization technique. ; # EXPERIMENTAL DATA _diffrn_ambient_temperature 195.0(1) _diffrn_ambient_pressure 100 _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 \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 4591 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0128 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.77 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1076 _reflns_number_gt 927 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisCCD (Oxford Diffraction, 2007)' _computing_cell_refinement 'CrysAlisRED (Oxford Diffraction, 2007)' _computing_data_reduction 'CrysAlisRED (Oxford Diffraction, 2007)' _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. ; _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^)+(0.0340P)^2^+3.5032P] 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 SHELXL _refine_ls_extinction_coef 0.0062(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1076 _refine_ls_number_parameters 75 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.0940 _refine_ls_wR_factor_gt 0.0898 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.553 _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 Cl1 Cl 0.69355(6) -0.0148(2) 0.49137(13) 0.0596(5) Uani 1 1 d . . . Cl2 Cl 0.68800(7) 0.3780(2) 0.68212(14) 0.0653(5) Uani 1 1 d U . . Cl3 Cl 0.59541(10) 0.3684(3) 0.40967(15) 0.0936(7) Uani 1 1 d . . . Cl4 Cl 0.54923(7) 0.2019(3) 0.65110(17) 0.0874(6) Uani 1 1 d U . . C11 C 0.6441(5) 0.1851(13) 0.5469(7) 0.042(2) Uani 0.69(2) 1 d P A 1 C21 C 0.6014(4) 0.0270(15) 0.5978(8) 0.050(3) Uani 0.69(2) 1 d P A 1 H211 H 0.6275 -0.0700 0.6738 0.060 Uiso 0.69(2) 1 calc PR A 1 H212 H 0.5771 -0.0793 0.5247 0.060 Uiso 0.69(2) 1 calc PR A 1 C12 C 0.6151(11) 0.229(4) 0.5741(17) 0.045(6) Uani 0.31(2) 1 d P A 2 C22 C 0.6331(10) -0.017(3) 0.5621(18) 0.049(7) Uani 0.31(2) 1 d P A 2 H221 H 0.5967 -0.1058 0.5036 0.059 Uiso 0.31(2) 1 calc PR A 2 H222 H 0.6481 -0.0918 0.6518 0.059 Uiso 0.31(2) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0575(8) 0.0680(8) 0.0592(8) -0.0038(6) 0.0275(6) 0.0087(6) Cl2 0.0713(8) 0.0612(8) 0.0576(8) -0.0106(6) 0.0142(6) -0.0235(6) Cl3 0.1402(16) 0.0719(10) 0.0473(8) 0.0146(7) 0.0039(8) 0.0333(10) Cl4 0.0526(8) 0.1299(14) 0.0869(10) -0.0522(10) 0.0329(7) -0.0126(8) C11 0.044(5) 0.044(4) 0.037(4) 0.003(3) 0.013(3) 0.002(3) C21 0.043(5) 0.063(5) 0.048(4) -0.013(3) 0.021(3) -0.013(3) C12 0.038(10) 0.053(11) 0.035(8) -0.001(7) 0.002(7) -0.006(8) C22 0.050(12) 0.051(10) 0.046(9) -0.004(7) 0.015(8) -0.010(8) # 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 Cl1 C11 1.797(11) . ? Cl1 C22 1.74(3) . ? Cl2 C11 1.776(7) . ? Cl2 C12 1.830(15) . ? Cl3 C11 1.788(7) . ? Cl3 C12 1.787(16) . ? Cl4 C12 1.90(3) . ? Cl4 C21 1.747(11) . ? C11 C21 1.519(16) . ? C12 C22 1.45(4) . ? C21 H211 0.9700 . ? C21 H212 0.9700 . ? C22 H221 0.9700 . ? C22 H222 0.9700 . ? 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 C21 C11 Cl2 108.8(7) . . ? C21 C11 Cl3 109.2(7) . . ? Cl2 C11 Cl3 107.5(4) . . ? C21 C11 Cl1 105.8(6) . . ? Cl2 C11 Cl1 113.4(5) . . ? Cl3 C11 Cl1 112.0(5) . . ? C11 C21 Cl4 110.2(7) . . ? C11 C21 H211 109.6 . . ? Cl4 C21 H211 109.6 . . ? C11 C21 H212 109.6 . . ? Cl4 C21 H212 109.6 . . ? H211 C21 H212 108.1 . . ? C22 C12 Cl3 108.5(18) . . ? C22 C12 Cl2 105.7(17) . . ? Cl3 C12 Cl2 105.2(9) . . ? C22 C12 Cl4 103.7(15) . . ? Cl3 C12 Cl4 117.5(12) . . ? Cl2 C12 Cl4 115.6(12) . . ? C12 C22 Cl1 108.0(17) . . ? C12 C22 H221 110.1 . . ? Cl1 C22 H221 110.1 . . ? C12 C22 H222 110.1 . . ? Cl1 C22 H222 110.1 . . ? H221 C22 H222 108.4 . . ? 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 Cl2 C11 C21 Cl4 59.2(7) . . . . ? Cl3 C11 C21 Cl4 -57.8(7) . . . . ? Cl1 C11 C21 Cl4 -178.5(3) . . . . ? Cl3 C12 C22 Cl1 54.1(15) . . . . ? Cl2 C12 C22 Cl1 -58.3(14) . . . . ? Cl4 C12 C22 Cl1 179.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.578 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.060 ############################################################################# data_1112TCE_100K _database_code_depnum_ccdc_archive 'CCDC 746845' #TrackingRef '1112TCE_CIF_LT_HPall16.cif' # CHEMICAL DATA _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,1,2-tetrachloroethane ; _chemical_name_common 1,1,1,2-tetrachloroethane _chemical_melting_point ? _chemical_formula_moiety 'C2 H2 Cl4' _chemical_formula_sum 'C2 H2 Cl4' _chemical_formula_weight 167.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.1891(15) _cell_length_b 5.4975(2) _cell_length_c 10.2493(6) _cell_angle_alpha 90.00 _cell_angle_beta 110.055(7) _cell_angle_gamma 90.00 _cell_volume 1174.45(12) _cell_formula_units_Z 8 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 3882 _cell_measurement_theta_min 3.75 _cell_measurement_theta_max 30.04 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.898 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 1.864 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6048 _exptl_absorpt_correction_T_max 0.7069 _exptl_absorpt_process_details ; Correction for absorption was made using CrysAlisRED (Oxford Diffraction, 2007). ; _exptl_special_details ; Data were collected at ambient pressure (100 kPa) and 100 K with the crystal obtained by the in-situ low-temperature crystallization technique. ; # EXPERIMENTAL DATA _diffrn_ambient_temperature 100.0(1) _diffrn_ambient_pressure 100 _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 \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 4398 _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_sigmaI/netI 0.0117 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.83 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1034 _reflns_number_gt 944 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisCCD (Oxford Diffraction, 2007)' _computing_cell_refinement 'CrysAlisRED (Oxford Diffraction, 2007)' _computing_data_reduction 'CrysAlisRED (Oxford Diffraction, 2007)' _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. ; _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^)+(0.0089P)^2^+3.8001P] 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 SHELXL _refine_ls_extinction_coef 0.0013(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1034 _refine_ls_number_parameters 75 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0294 _refine_ls_R_factor_gt 0.0261 _refine_ls_wR_factor_ref 0.0543 _refine_ls_wR_factor_gt 0.0523 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.317 _refine_ls_shift/su_max 0.001 _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 Cl1 Cl 0.69409(3) -0.01567(14) 0.48899(7) 0.0329(2) Uani 1 1 d . . . Cl2 Cl 0.68902(4) 0.37962(15) 0.68299(8) 0.0413(2) Uani 1 1 d U . . Cl3 Cl 0.59493(5) 0.37070(17) 0.40782(8) 0.0591(3) Uani 1 1 d . . . Cl4 Cl 0.54904(4) 0.19685(19) 0.65215(9) 0.0524(3) Uani 1 1 d U . . C11 C 0.6446(3) 0.1843(8) 0.5459(4) 0.0226(15) Uani 0.702(15) 1 d P A 1 C21 C 0.6018(3) 0.0208(9) 0.5973(5) 0.0291(15) Uani 0.702(15) 1 d P A 1 H211 H 0.6282 -0.0783 0.6739 0.035 Uiso 0.702(15) 1 calc PR A 1 H212 H 0.5774 -0.0871 0.5231 0.035 Uiso 0.702(15) 1 calc PR A 1 C12 C 0.6144(7) 0.227(2) 0.5746(11) 0.032(4) Uani 0.298(15) 1 d P A 2 C22 C 0.6325(7) -0.018(2) 0.5618(12) 0.034(4) Uani 0.298(15) 1 d P A 2 H221 H 0.5958 -0.1086 0.5024 0.041 Uiso 0.298(15) 1 calc PR A 2 H222 H 0.6476 -0.0952 0.6523 0.041 Uiso 0.298(15) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0323(4) 0.0380(4) 0.0305(4) -0.0013(3) 0.0136(3) 0.0051(3) Cl2 0.0490(5) 0.0372(4) 0.0302(4) -0.0033(3) 0.0038(3) -0.0176(4) Cl3 0.0917(8) 0.0428(5) 0.0248(4) 0.0071(4) -0.0032(4) 0.0200(5) Cl4 0.0307(4) 0.0802(7) 0.0499(5) -0.0350(5) 0.0183(4) -0.0093(4) C11 0.023(3) 0.027(2) 0.018(2) 0.0009(17) 0.0061(19) 0.0018(19) C21 0.024(3) 0.039(3) 0.028(2) -0.010(2) 0.014(2) -0.009(2) C12 0.024(7) 0.046(8) 0.019(5) 0.002(5) 0.000(5) -0.010(6) C22 0.033(8) 0.038(7) 0.027(6) 0.003(5) 0.005(5) -0.008(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 Cl1 C11 1.787(6) . ? Cl1 C22 1.768(18) . ? Cl2 C11 1.775(4) . ? Cl2 C12 1.849(10) . ? Cl3 C11 1.788(4) . ? Cl3 C12 1.796(11) . ? Cl4 C12 1.884(18) . ? Cl4 C21 1.753(6) . ? C11 C21 1.527(9) . ? C12 C22 1.42(3) . ? C21 H211 0.9700 . ? C21 H212 0.9700 . ? C22 H221 0.9700 . ? C22 H222 0.9700 . ? 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 C21 C11 Cl2 109.0(4) . . ? C21 C11 Cl3 108.8(4) . . ? Cl2 C11 Cl3 107.7(2) . . ? C21 C11 Cl1 106.0(3) . . ? Cl2 C11 Cl1 113.2(3) . . ? Cl1 C11 Cl3 112.0(3) . . ? C11 C21 Cl4 110.4(4) . . ? C11 C21 H211 109.6 . . ? Cl4 C21 H211 109.6 . . ? C11 C21 H212 109.6 . . ? Cl4 C21 H212 109.6 . . ? H211 C21 H212 108.1 . . ? C22 C12 Cl3 108.1(12) . . ? C22 C12 Cl2 105.2(11) . . ? Cl3 C12 Cl2 104.2(6) . . ? C22 C12 Cl4 103.8(10) . . ? Cl3 C12 Cl4 118.1(8) . . ? Cl2 C12 Cl4 116.5(8) . . ? C12 C22 Cl1 108.4(11) . . ? C12 C22 H221 110.0 . . ? Cl1 C22 H221 110.0 . . ? C12 C22 H222 110.0 . . ? Cl1 C22 H222 110.0 . . ? H221 C22 H222 108.4 . . ? 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 Cl2 C11 C21 Cl4 59.4(4) . . . . ? Cl3 C11 C21 Cl4 -57.8(4) . . . . ? Cl1 C11 C21 Cl4 -178.4(2) . . . . ? Cl3 C12 C22 Cl1 53.6(10) . . . . ? Cl2 C12 C22 Cl1 -57.3(9) . . . . ? Cl4 C12 C22 Cl1 179.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.616 _refine_diff_density_min -0.592 _refine_diff_density_rms 0.056 ############################################################################# data_1112TCE_105GPa _database_code_depnum_ccdc_archive 'CCDC 746846' #TrackingRef '1112TCE_CIF_LT_HPall16.cif' # CHEMICAL DATA _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,2,2-tetrachloroethane ; _chemical_name_common 1,1,2,2-tetrachloroethane _chemical_melting_point ? _chemical_formula_moiety 'C2 H2 Cl4' _chemical_formula_sum 'C2 H2 Cl4' _chemical_formula_weight 167.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' # CRYSTAL DATA _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 5.7549(14) _cell_length_b 11.979(7) _cell_length_c 8.734(5) _cell_angle_alpha 90.00 _cell_angle_beta 110.32(4) _cell_angle_gamma 90.00 _cell_volume 564.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2929 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 27.48 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.974 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 1.939 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.63 _exptl_absorpt_correction_T_max 0.68 _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 1.05(5) GPa (1050000 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 1050000 _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 3635 _diffrn_reflns_av_R_equivalents 0.2175 _diffrn_reflns_av_sigmaI/netI 0.2842 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 24.96 _reflns_number_total 515 _reflns_number_gt 488 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisCCD (Oxford Diffraction, 2007)' _computing_cell_refinement 'CrysAlisRED (Oxford Diffraction, 2007)' _computing_data_reduction 'CrysAlisRED (Oxford Diffraction, 2007); 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^)+(0.1035P)^2^+2.3159P] 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 515 _refine_ls_number_parameters 55 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1269 _refine_ls_R_factor_gt 0.0861 _refine_ls_wR_factor_ref 0.2024 _refine_ls_wR_factor_gt 0.1978 _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_restrained_S_all 1.142 _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 Cl1 Cl 0.4180(4) 0.7738(3) 0.3084(3) 0.0540(9) Uani 1 1 d . . . Cl2 Cl 0.0118(4) 0.6574(3) 0.0681(3) 0.0521(9) Uani 1 1 d . . . Cl3 Cl 0.5010(4) 0.5588(2) 0.1913(4) 0.0538(10) Uani 1 1 d . . . Cl4 Cl 0.1121(4) 0.4516(2) 0.3398(3) 0.0460(9) Uani 1 1 d . . . C1 C 0.2864(14) 0.6408(8) 0.2415(11) 0.033(2) Uani 1 1 d U . . C2 C 0.2259(16) 0.5903(8) 0.3837(12) 0.039(2) Uani 1 1 d U . . H21 H 0.1026 0.6360 0.4063 0.047 Uiso 1 1 calc R . . H22 H 0.3741 0.5900 0.4805 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0552(14) 0.041(3) 0.060(3) -0.0047(10) 0.0122(13) -0.0115(12) Cl2 0.0426(12) 0.066(3) 0.037(3) 0.0118(10) -0.0001(11) -0.0057(11) Cl3 0.0570(15) 0.057(3) 0.065(3) 0.0043(11) 0.0433(15) 0.0102(12) Cl4 0.0542(14) 0.044(3) 0.045(2) -0.0006(9) 0.0236(12) -0.0085(11) C1 0.033(4) 0.033(6) 0.034(6) 0.002(3) 0.012(4) 0.006(3) C2 0.044(4) 0.033(7) 0.041(6) -0.004(3) 0.014(4) -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 Cl1 C1 1.774(10) . ? Cl2 C1 1.780(8) . ? Cl3 C1 1.749(9) . ? Cl4 C2 1.778(10) . ? C1 C2 1.527(13) . ? C2 H21 0.9700 . ? C2 H22 0.9700 . ? 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 C1 Cl3 111.2(6) . . ? C2 C1 Cl1 106.3(6) . . ? Cl3 C1 Cl1 109.2(4) . . ? C2 C1 Cl2 110.5(6) . . ? Cl3 C1 Cl2 110.2(5) . . ? Cl1 C1 Cl2 109.4(5) . . ? C1 C2 Cl4 111.5(7) . . ? C1 C2 H21 109.3 . . ? Cl4 C2 H21 109.3 . . ? C1 C2 H22 109.3 . . ? Cl4 C2 H22 109.3 . . ? H21 C2 H22 108.0 . . ? 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 Cl3 C1 C2 Cl4 -57.0(8) . . . . ? Cl1 C1 C2 Cl4 -175.8(4) . . . . ? Cl2 C1 C2 Cl4 65.6(7) . . . . ? _diffrn_measured_fraction_theta_max 0.520 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.520 _refine_diff_density_max 0.471 _refine_diff_density_min -0.423 _refine_diff_density_rms 0.124 ############################################################################# data_1112TCE_165GPa _database_code_depnum_ccdc_archive 'CCDC 746847' #TrackingRef '1112TCE_CIF_LT_HPall16.cif' # CHEMICAL DATA _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,2,2-tetrachloroethane ; _chemical_name_common 1,1,2,2-tetrachloroethane _chemical_melting_point ? _chemical_formula_moiety 'C2 H2 Cl4' _chemical_formula_sum 'C2 H2 Cl4' _chemical_formula_weight 167.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' # CRYSTAL DATA _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 5.6957(14) _cell_length_b 11.850(7) _cell_length_c 8.610(5) _cell_angle_alpha 90.00 _cell_angle_beta 110.35(4) _cell_angle_gamma 90.00 _cell_volume 544.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3282 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 28.18 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.046 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 2.009 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.54 _exptl_absorpt_correction_T_max 0.60 _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 1.65(5) GPa (1650000 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 1650000 _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 3565 _diffrn_reflns_av_R_equivalents 0.1536 _diffrn_reflns_av_sigmaI/netI 0.0629 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 25.00 _reflns_number_total 500 _reflns_number_gt 478 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisCCD (Oxford Diffraction, 2007)' _computing_cell_refinement 'CrysAlisRED (Oxford Diffraction, 2007)' _computing_data_reduction 'CrysAlisRED (Oxford Diffraction, 2007); 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^)+(0.1014P)^2^+0.9441P] 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 500 _refine_ls_number_parameters 55 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0713 _refine_ls_R_factor_gt 0.0691 _refine_ls_wR_factor_ref 0.1729 _refine_ls_wR_factor_gt 0.1707 _refine_ls_goodness_of_fit_ref 1.180 _refine_ls_restrained_S_all 1.165 _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 Cl1 Cl 0.4212(3) 0.77469(18) 0.3103(3) 0.0452(7) Uani 1 1 d . . . Cl2 Cl 0.0107(3) 0.65811(19) 0.0659(2) 0.0444(8) Uani 1 1 d . . . Cl3 Cl 0.5053(3) 0.55792(18) 0.1910(3) 0.0449(8) Uani 1 1 d . . . Cl4 Cl 0.1124(3) 0.44924(17) 0.3409(3) 0.0386(7) Uani 1 1 d . . . C1 C 0.2859(11) 0.6401(6) 0.2425(9) 0.0286(17) Uani 1 1 d U . . C2 C 0.2227(12) 0.5892(6) 0.3839(10) 0.0333(18) Uani 1 1 d U . . H21 H 0.0957 0.6349 0.4049 0.040 Uiso 1 1 calc R . . H22 H 0.3708 0.5898 0.4832 0.040 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0461(11) 0.033(2) 0.051(2) -0.0055(7) 0.0104(10) -0.0094(8) Cl2 0.0360(10) 0.055(2) 0.033(2) 0.0105(7) 0.0007(9) -0.0053(8) Cl3 0.0478(11) 0.046(2) 0.056(2) 0.0041(8) 0.0373(11) 0.0100(8) Cl4 0.0436(10) 0.036(2) 0.040(2) -0.0011(7) 0.0202(10) -0.0080(7) C1 0.025(3) 0.025(6) 0.036(6) 0.001(2) 0.010(3) 0.000(3) C2 0.038(3) 0.035(7) 0.030(7) -0.002(3) 0.016(3) 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 Cl1 C1 1.779(8) . ? Cl2 C1 1.777(7) . ? Cl3 C1 1.759(7) . ? Cl4 C2 1.766(8) . ? C1 C2 1.510(10) . ? C2 H21 0.9700 . ? C2 H22 0.9700 . ? 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 C1 Cl3 111.8(5) . . ? C2 C1 Cl2 110.5(4) . . ? Cl3 C1 Cl2 110.1(4) . . ? C2 C1 Cl1 106.9(5) . . ? Cl3 C1 Cl1 108.3(3) . . ? Cl2 C1 Cl1 109.0(4) . . ? C1 C2 Cl4 111.9(5) . . ? C1 C2 H21 109.2 . . ? Cl4 C2 H21 109.2 . . ? C1 C2 H22 109.2 . . ? Cl4 C2 H22 109.2 . . ? H21 C2 H22 107.9 . . ? 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 Cl3 C1 C2 Cl4 -56.2(6) . . . . ? Cl2 C1 C2 Cl4 66.8(5) . . . . ? Cl1 C1 C2 Cl4 -174.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.521 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.521 _refine_diff_density_max 0.434 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.116 ############################################################################# data_1112TCE_255GPa _database_code_depnum_ccdc_archive 'CCDC 746848' #TrackingRef '1112TCE_CIF_LT_HPall16.cif' # CHEMICAL DATA _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1,2,2-tetrachloroethane ; _chemical_name_common 1,1,2,2-tetrachloroethane _chemical_melting_point ? _chemical_formula_moiety 'C2 H2 Cl4' _chemical_formula_sum 'C2 H2 Cl4' _chemical_formula_weight 167.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' # CRYSTAL DATA _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 5.5937(14) _cell_length_b 11.586(6) _cell_length_c 8.336(5) _cell_angle_alpha 90.00 _cell_angle_beta 110.60(4) _cell_angle_gamma 90.00 _cell_volume 505.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2858 _cell_measurement_theta_min 3.14 _cell_measurement_theta_max 28.90 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.204 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 2.164 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.54 _exptl_absorpt_correction_T_max 0.59 _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 2.55(5) GPa (2550000 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 2550000 _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 3193 _diffrn_reflns_av_R_equivalents 0.2712 _diffrn_reflns_av_sigmaI/netI 0.1002 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 24.90 _reflns_number_total 443 _reflns_number_gt 404 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisCCD (Oxford Diffraction, 2007)' _computing_cell_refinement 'CrysAlisRED (Oxford Diffraction, 2007)' _computing_data_reduction 'CrysAlisRED (Oxford Diffraction, 2007); 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^)+(0.1535P)^2^+0.9252P] 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 443 _refine_ls_number_parameters 55 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0973 _refine_ls_R_factor_gt 0.0901 _refine_ls_wR_factor_ref 0.2365 _refine_ls_wR_factor_gt 0.2272 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.140 _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 Cl1 Cl 0.4258(4) 0.7769(3) 0.3145(4) 0.0417(11) Uani 1 1 d . . . Cl2 Cl 0.0091(4) 0.6591(3) 0.0610(3) 0.0402(11) Uani 1 1 d . . . Cl3 Cl 0.5118(4) 0.5567(2) 0.1910(4) 0.0402(10) Uani 1 1 d . . . Cl4 Cl 0.1140(4) 0.4442(2) 0.3426(4) 0.0379(10) Uani 1 1 d . . . C1 C 0.2885(14) 0.6432(9) 0.2431(14) 0.030(2) Uani 1 1 d U . . C2 C 0.2214(17) 0.5857(10) 0.3882(16) 0.039(3) Uani 1 1 d U . . H21 H 0.0902 0.6310 0.4100 0.047 Uiso 1 1 calc R . . H22 H 0.3715 0.5862 0.4918 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0360(14) 0.036(3) 0.049(3) -0.0052(9) 0.0109(13) -0.0064(10) Cl2 0.0290(13) 0.048(3) 0.038(3) 0.0075(9) 0.0047(13) -0.0045(9) Cl3 0.0434(14) 0.035(3) 0.055(3) 0.0037(10) 0.0329(15) 0.0069(10) Cl4 0.0381(14) 0.037(3) 0.043(3) -0.0008(9) 0.0198(14) -0.0084(10) C1 0.017(4) 0.032(9) 0.041(9) 0.005(3) 0.010(4) 0.002(4) C2 0.030(4) 0.035(10) 0.054(10) -0.005(4) 0.017(5) -0.011(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 Cl1 C1 1.739(11) . ? Cl2 C1 1.764(9) . ? Cl3 C1 1.770(10) . ? Cl4 C2 1.741(11) . ? C1 C2 1.537(15) . ? C2 H21 0.9700 . ? C2 H22 0.9700 . ? 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 C1 Cl1 108.5(8) . . ? C2 C1 Cl2 109.5(6) . . ? Cl1 C1 Cl2 110.6(5) . . ? C2 C1 Cl3 109.7(7) . . ? Cl1 C1 Cl3 108.9(4) . . ? Cl2 C1 Cl3 109.6(6) . . ? C1 C2 Cl4 113.4(8) . . ? C1 C2 H21 108.9 . . ? Cl4 C2 H21 108.9 . . ? C1 C2 H22 108.9 . . ? Cl4 C2 H22 108.9 . . ? H21 C2 H22 107.7 . . ? 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 Cl1 C1 C2 Cl4 -173.4(5) . . . . ? Cl2 C1 C2 Cl4 65.7(8) . . . . ? Cl3 C1 C2 Cl4 -54.6(8) . . . . ? _diffrn_measured_fraction_theta_max 0.503 _diffrn_reflns_theta_full 24.90 _diffrn_measured_fraction_theta_full 0.503 _refine_diff_density_max 0.746 _refine_diff_density_min -0.541 _refine_diff_density_rms 0.178 #############################################################################