# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_author_address ;Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznan Poland ; loop_ _publ_author_footnote ; Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznan Poland ; _publ_contact_author_address ;Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznan Poland ; _publ_contact_author_email katran@amu.edu.pl _publ_contact_author_fax +48(61)8658008 _publ_contact_author_phone +48(61)8291443 _publ_contact_author_name 'Andrzej Katrusiak' _publ_section_title ; Electrostatic matching and structure-property relations of acetonitrile and its chloric derivatives ; loop_ _publ_author_name A.Olejniczak A.Katrusiak data_CAN _database_code_depnum_ccdc_archive 'CCDC 751844' _audit_creation_method SHELXL-97 _chemical_name_systematic ; chloroacetonitrile ; _chemical_name_common chloroacetonitrile _chemical_formula_moiety 'C2 H2 Cl1 N1' _chemical_formula_sum 'C2 H2 Cl1 N1' _chemical_formula_weight 75.50 _chemical_melting_point ? _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P bca' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.7821(16) _cell_length_b 7.0635(14) _cell_length_c 11.620(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 638.7(2) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_pressure 1300000 _cell_measurement_reflns_used 467 _cell_measurement_theta_min 4.27 _cell_measurement_theta_max 29.14 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.570 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.904 _exptl_absorpt_correction_type integration _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_absorpt_correction_T_min 0.57 _exptl_absorpt_correction_T_max 0.95 _exptl_special_details ; Data were collected at room temperature and pressure of 1.30(5) GPa (1300000 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_ambient_environment 'diamond-anvil cell' _diffrn_ambient_pressure 1300000 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _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 16.4 _diffrn_reflns_number 3723 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_theta_min 4.27 _diffrn_reflns_theta_max 29.14 _diffrn_reflns_theta_full 29.14 _diffrn_measured_fraction_theta_max 0.544 _diffrn_measured_fraction_theta_full 0.544 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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. ; _reflns_number_total 467 _reflns_number_gt 430 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1043 _refine_ls_wR_factor_gt 0.0995 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_number_reflns 467 _refine_ls_number_parameters 37 _refine_ls_number_restraints 0 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0434P)^2^+0.4815P] 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_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.148 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.042 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' N N 0.0061 0.0033 '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' _computing_data_collection 'CrysAlis (Oxford Diffraction, 2002)' _computing_cell_refinement 'CrysAlis (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis (Oxford Diffraction, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;X-Seed (Barbour, 2001) and POV-Ray (Persistence of Vision, 2004) ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' 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 0.42492(11) 0.24502(11) 0.28755(8) 0.0579(4) Uani 1 1 d . . . C1 C 0.3557(3) 0.1247(3) 0.0755(3) 0.0381(7) Uani 1 1 d . . . N1 N 0.2567(3) 0.0438(3) 0.0239(3) 0.0509(7) Uani 1 1 d . . . C2 C 0.4848(4) 0.2271(3) 0.1409(3) 0.0422(7) Uani 1 1 d . . . H1 H 0.4988 0.3530 0.1088 0.051 Uiso 1 1 calc R . . H2 H 0.5942 0.1618 0.1349 0.051 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 0.0579(7) 0.0766(6) 0.0393(9) -0.0111(3) 0.0031(3) -0.0096(3) C1 0.0381(16) 0.0409(13) 0.035(2) 0.0028(10) 0.0049(10) 0.0053(10) N1 0.0537(17) 0.0522(13) 0.047(2) -0.0002(11) -0.0051(11) -0.0004(11) C2 0.0384(17) 0.0499(14) 0.038(2) -0.0013(11) 0.0031(11) -0.0046(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.772(3) . ? C1 N1 1.131(4) . ? C1 C2 1.452(4) . ? C2 H1 0.9700 . ? C2 H2 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 N1 C1 C2 179.1(3) . . ? C1 C2 Cl1 110.9(2) . . ? C1 C2 H1 109.5 . . ? Cl1 C2 H1 109.5 . . ? C1 C2 H2 109.5 . . ? Cl1 C2 H2 109.5 . . ? H1 C2 H2 108.0 . . ? #AND data_dcan _database_code_depnum_ccdc_archive 'CCDC 751845' _audit_creation_method SHELXL-97 _chemical_name_systematic ; dichloroacetonitrile ; _chemical_name_common dichloroacetonitrile _chemical_melting_point ? _chemical_formula_moiety 'C2 H Cl2 N' _chemical_formula_sum 'C2 H Cl2 N' _chemical_formula_weight 109.94 _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 2(1)/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 5.9360(12) _cell_length_b 17.940(4) _cell_length_c 7.5470(15) _cell_angle_alpha 90.00 _cell_angle_beta 92.44(3) _cell_angle_gamma 90.00 _cell_volume 803.0(3) _cell_formula_units_Z 8 _cell_measurement_reflns_used 640 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 29.96 _cell_measurement_temperature 296(2) _cell_measurement_pressure 1000000 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.819 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 1.394 _exptl_absorpt_correction_type integration _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_absorpt_correction_T_min 0.39 _exptl_absorpt_correction_T_max 0.79 _exptl_special_details ; Data were collected at room temperature and pressure of 1.00(5) GPa (1000000 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_ambient_environment 'diamond-anvil cell' _diffrn_ambient_pressure 1000000 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _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 16.4 _diffrn_reflns_number 5955 _diffrn_reflns_av_R_equivalents 0.1656 _diffrn_reflns_av_sigmaI/netI 0.1157 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 29.96 _diffrn_measured_fraction_theta_max 0.272 _diffrn_reflns_theta_full 29.96 _diffrn_measured_fraction_theta_full 0.272 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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. ; _reflns_number_total 640 _reflns_number_gt 322 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.2091 _refine_ls_R_factor_gt 0.0794 _refine_ls_wR_factor_ref 0.1994 _refine_ls_wR_factor_gt 0.1439 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_number_reflns 640 _refine_ls_number_parameters 61 _refine_ls_number_restraints 0 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0772P)^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_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.272 _refine_diff_density_min -0.299 _refine_diff_density_rms 0.072 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' N N 0.0061 0.0033 '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' _computing_data_collection 'CrysAlis (Oxford Diffraction, 2002)' _computing_cell_refinement 'CrysAlis (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis (Oxford Diffraction, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;X-Seed (Barbour, 2001) and POV-Ray (Persistence of Vision, 2004) ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' 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 Cl3 Cl -0.1520(4) 0.5883(5) -0.0509(4) 0.065(7) Uani 1 1 d . . . N1 N 0.4894(16) 0.7482(15) 0.5348(16) 0.062(3) Uiso 1 1 d . . . C2 C 0.6096(13) 0.6369(16) 0.3541(11) 0.025(3) Uiso 1 1 d . . . H1 H 0.6674 0.6551 0.2423 0.030 Uiso 1 1 calc R . . Cl4 Cl 0.2854(4) 0.5813(5) -0.2071(4) 0.091(8) Uani 1 1 d . . . C4 C 0.0929(16) 0.644(2) -0.0958(14) 0.048(3) Uiso 1 1 d . . . H2 H 0.1640 0.6615 0.0158 0.058 Uiso 1 1 calc R . . C3 C 0.0352(17) 0.7010(19) -0.1985(16) 0.033(3) Uiso 1 1 d . . . Cl2 Cl 0.8302(4) 0.5891(5) 0.4670(4) 0.066(8) Uani 1 1 d . . . C1 C 0.5378(16) 0.7006(18) 0.4524(15) 0.034(3) Uiso 1 1 d . . . Cl1 Cl 0.3854(4) 0.5763(5) 0.3008(4) 0.054(7) Uani 1 1 d . . . N2 N -0.0030(16) 0.7602(18) -0.2697(15) 0.052(3) Uiso 1 1 d . . . 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 Cl3 0.0553(18) 0.08(2) 0.0597(18) 0.004(4) 0.0215(13) -0.007(4) Cl4 0.0493(17) 0.16(2) 0.0652(19) -0.004(4) 0.0161(13) 0.014(4) Cl2 0.0579(19) 0.08(2) 0.0615(19) -0.011(4) -0.0136(13) 0.009(4) Cl1 0.0502(17) 0.05(2) 0.0606(18) 0.008(4) -0.0070(12) -0.002(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 Cl3 C4 1.80(2) . ? N1 C1 1.10(3) . ? C2 C1 1.44(3) . ? C2 Cl1 1.75(2) . ? C2 Cl2 1.755(17) . ? C2 H1 0.9800 . ? Cl4 C4 1.83(2) . ? C4 C3 1.32(4) . ? C4 H2 0.9800 . ? C3 N2 1.21(4) . ? 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 C2 Cl1 111.9(8) . . ? C1 C2 Cl2 111.7(8) . . ? Cl1 C2 Cl2 110.6(16) . . ? C1 C2 H1 107.5 . . ? Cl1 C2 H1 107.5 . . ? Cl2 C2 H1 107.5 . . ? C3 C4 Cl3 110.3(9) . . ? C3 C4 Cl4 110.9(10) . . ? Cl3 C4 Cl4 105.9(18) . . ? C3 C4 H2 109.9 . . ? Cl3 C4 H2 109.9 . . ? Cl4 C4 H2 109.9 . . ? N2 C3 C4 169(3) . . ? N1 C1 C2 176.4(19) . . ? #AND data_TCAN _database_code_depnum_ccdc_archive 'CCDC 751846' _audit_creation_method SHELXL-97 _chemical_name_systematic ; trichloroacetonitrile ; _chemical_name_common trichloroacetonitrile _chemical_formula_moiety 'C2 Cl3 N' _chemical_formula_sum 'C2 Cl3 N' _chemical_formula_weight 144.38 _chemical_melting_point 357 _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'I 4(1)cd' _symmetry_space_group_name_Hall 'I 4bw -2c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-y, x+1/2, z+1/4' 'y+1/2, -x, z+3/4' 'x, -y, z+1/2' '-x+1/2, y+1/2, z' '-y, -x+1/2, z+3/4' 'y+1/2, x, z+1/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1, z+1' '-y+1/2, x+1, z+3/4' 'y+1, -x+1/2, z+5/4' 'x+1/2, -y+1/2, z+1' '-x+1, y+1, z+1/2' '-y+1/2, -x+1, z+5/4' 'y+1, x+1/2, z+3/4' _cell_length_a 15.251(2) _cell_length_b 15.251(2) _cell_length_c 8.1219(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1889.0(5) _cell_formula_units_Z 16 _cell_measurement_temperature 296(2) _cell_measurement_pressure 900000 _cell_measurement_reflns_used 822 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 29.29 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.031 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 1.759 _exptl_absorpt_correction_type integration _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_absorpt_correction_T_min 0.30 _exptl_absorpt_correction_T_max 0.64 _exptl_special_details ; Data were collected at room temperature and pressure of 0.90(5) GPa (900000 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_ambient_environment 'diamond-anvil cell' _diffrn_ambient_pressure 900000 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _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 16.4 _diffrn_reflns_number 5562 _diffrn_reflns_av_R_equivalents 0.1219 _diffrn_reflns_av_sigmaI/netI 0.0418 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 29.29 _diffrn_reflns_theta_full 29.29 _diffrn_measured_fraction_theta_max 0.645 _diffrn_measured_fraction_theta_full 0.645 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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. ; _reflns_number_total 822 _reflns_number_gt 729 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0707 _refine_ls_R_factor_gt 0.0636 _refine_ls_wR_factor_ref 0.1724 _refine_ls_wR_factor_gt 0.1613 _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_restrained_S_all 1.124 _refine_ls_number_reflns 822 _refine_ls_number_parameters 55 _refine_ls_number_restraints 1 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0915P)^2^+9.5586P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.538 _refine_diff_density_min -0.527 _refine_diff_density_rms 0.126 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.7(4) 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' N N 0.0061 0.0033 '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' _computing_data_collection 'CrysAlis (Oxford Diffraction, 2002)' _computing_cell_refinement 'CrysAlis (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis (Oxford Diffraction, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;X-Seed (Barbour, 2001) and POV-Ray (Persistence of Vision, 2004) ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' 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 Cl3 Cl 0.15240(15) 0.15665(15) 0.1553(3) 0.0458(5) Uani 1 1 d . . . Cl2 Cl 0.04287(12) 0.12449(16) 0.4383(2) 0.0496(6) Uani 1 1 d . . . Cl1 Cl 0.14742(15) -0.01589(12) 0.3016(3) 0.0481(6) Uani 1 1 d . . . N1 N 0.2728(5) 0.1379(5) 0.5344(8) 0.0424(16) Uani 1 1 d . . . C2 C 0.1439(5) 0.0988(6) 0.3417(8) 0.0380(17) Uani 1 1 d . . . C1 C 0.2160(5) 0.1205(5) 0.4496(8) 0.0313(14) Uani 1 1 d . . . 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 Cl3 0.0520(11) 0.0464(11) 0.0390(8) 0.0057(8) -0.0061(8) -0.0040(12) Cl2 0.0288(9) 0.0596(13) 0.0604(11) -0.0143(10) 0.0054(8) -0.0020(13) Cl1 0.0579(11) 0.0308(9) 0.0554(10) -0.0040(8) 0.0043(10) -0.0032(13) N1 0.037(3) 0.052(4) 0.038(3) 0.005(3) -0.003(3) 0.002(4) C2 0.035(3) 0.043(4) 0.036(3) -0.001(3) -0.004(3) -0.005(5) C1 0.035(3) 0.029(3) 0.030(3) 0.001(3) 0.004(3) 0.003(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 Cl3 C2 1.757(8) . ? Cl2 C2 1.773(8) . ? Cl1 C2 1.780(9) . ? N1 C1 1.138(10) . ? C2 C1 1.443(10) . ? 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 C2 Cl3 110.6(6) . . ? C1 C2 Cl2 110.0(5) . . ? Cl3 C2 Cl2 109.5(5) . . ? C1 C2 Cl1 108.3(6) . . ? Cl3 C2 Cl1 109.5(4) . . ? Cl2 C2 Cl1 108.9(5) . . ? N1 C1 C2 179.7(9) . . ?