# 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 _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 ; Negative linear compression and expanding NH...N bond in an imidazoline compound ; loop_ _publ_author_name 'Aniola Michalina' A.Katrusiak 'Kia Reza' # AND data_0.08GPa _database_code_depnum_ccdc_archive 'CCDC 872961' #TrackingRef '- IMDZLNall.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic 2-(3-chlorophenyl)-imidazoline _chemical_name_common 2-(3-chlorophenyl)-imidazoline _chemical_melting_point 408 _chemical_formula_moiety 'C9 H9 Cl N2' _chemical_formula_sum 'C9 H9 Cl N2' _chemical_formula_weight 180.63 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fdd2 _symmetry_space_group_name_Hall 'F 2 -2d' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 19.875(6) _cell_length_b 39.36(3) _cell_length_c 4.398(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3441(5) _cell_formula_units_Z 16 _cell_measurement_temperature 296(2) _cell_measurement_pressure 80000 _cell_measurement_reflns_used 340 _cell_measurement_theta_min 4.10 _cell_measurement_theta_max 17.90 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas 1.395 _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.384 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.524 _exptl_absorpt_correction_T_max 0.884 _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 Data were collected at room temperature and pressure of 0.08(5) GPa (80000 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 16.4 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2242 _diffrn_reflns_av_R_equivalents 0.2946 _diffrn_reflns_av_sigmaI/netI 0.1363 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -3 _diffrn_reflns_limit_l_max 3 _diffrn_reflns_theta_min 4.10 _diffrn_reflns_theta_max 17.90 _reflns_number_total 340 _reflns_number_gt 300 _reflns_threshold_expression >2sigma(I) _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, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 2008' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.3(5) _refine_ls_number_reflns 340 _refine_ls_number_parameters 54 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1145 _refine_ls_R_factor_gt 0.0994 _refine_ls_wR_factor_ref 0.2367 _refine_ls_wR_factor_gt 0.2218 _refine_ls_goodness_of_fit_ref 1.291 _refine_ls_restrained_S_all 1.289 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.004 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 0.1657(3) 0.2467(2) 0.0229(13) 0.092(5) Uani 1 1 d . . . N1 N 0.0040(9) 0.1067(8) 0.189(3) 0.083(7) Uiso 1 1 d . . . H1 H -0.0334 0.1107 0.0979 0.100 Uiso 1 1 calc R . . N3 N 0.1098(7) 0.1171(7) 0.314(3) 0.057(5) Uiso 1 1 d . . . C7 C 0.1063(8) 0.1885(9) 0.069(5) 0.053(6) Uiso 1 1 d . . . H7 H 0.1400 0.1852 0.2132 0.064 Uiso 1 1 calc R . . C8 C 0.1032(8) 0.2172(9) -0.075(4) 0.040(6) Uiso 1 1 d . . . C9 C 0.0555(8) 0.2244(9) -0.256(4) 0.056(6) Uiso 1 1 d . . . H9 H 0.0540 0.2455 -0.3506 0.067 Uiso 1 1 calc R . . C10 C 0.0051(8) 0.2003(7) -0.313(4) 0.045(6) Uiso 1 1 d . . . H10 H -0.0299 0.2061 -0.4434 0.054 Uiso 1 1 calc R . . C11 C 0.0055(9) 0.1687(8) -0.185(4) 0.056(6) Uiso 1 1 d . . . H11 H -0.0281 0.1529 -0.2280 0.067 Uiso 1 1 calc R . . C6 C 0.0577(9) 0.1610(8) 0.010(4) 0.057(7) Uiso 1 1 d . . . C2 C 0.0597(9) 0.1282(8) 0.170(3) 0.043(6) Uiso 1 1 d . . . C5 C 0.0145(7) 0.0780(8) 0.370(4) 0.050(5) Uiso 1 1 d . . . H51 H 0.0076 0.0569 0.2592 0.060 Uiso 1 1 calc R . . H52 H -0.0126 0.0781 0.5531 0.060 Uiso 1 1 calc R . . C4 C 0.0922(9) 0.0854(10) 0.436(5) 0.071(7) Uiso 1 1 d . . . H41 H 0.1003 0.0853 0.6535 0.085 Uiso 1 1 calc R . . H42 H 0.1197 0.0677 0.3451 0.085 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 0.073(5) 0.067(15) 0.136(6) 0.011(6) -0.010(4) -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 Cl1 C8 1.75(3) . ? N1 C5 1.40(4) . ? N1 C2 1.40(3) . ? N3 C2 1.26(2) . ? N3 C4 1.40(4) . ? C7 C8 1.30(4) . ? C7 C6 1.47(4) . ? C8 C9 1.27(2) . ? C9 C10 1.40(3) . ? C10 C11 1.37(4) . ? C11 C6 1.38(2) . ? C6 C2 1.47(4) . ? C5 C4 1.60(2) . ? 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 C5 N1 C2 114.0(18) . . ? C2 N3 C4 107.7(16) . . ? C8 C7 C6 121(2) . . ? C7 C8 C9 122(3) . . ? C7 C8 Cl1 115.1(17) . . ? C9 C8 Cl1 122(2) . . ? C8 C9 C10 120(3) . . ? C11 C10 C9 123(2) . . ? C10 C11 C6 117(2) . . ? C11 C6 C2 121(2) . . ? C11 C6 C7 116(3) . . ? C2 C6 C7 122.8(19) . . ? N3 C2 C6 125(2) . . ? N3 C2 N1 113(2) . . ? C6 C2 N1 122.7(17) . . ? N1 C5 C4 96(2) . . ? N3 C4 C5 109(2) . . ? _diffrn_measured_fraction_theta_max 0.540 _diffrn_reflns_theta_full 17.90 _diffrn_measured_fraction_theta_full 0.540 _refine_diff_density_max 0.186 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.058 data_0.1MPa _database_code_depnum_ccdc_archive 'CCDC 872962' #TrackingRef '- IMDZLNall.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic 2-(3-chlorophenyl)-imidazoline _chemical_name_common 2-(3-chlorophenyl)-imidazoline _chemical_melting_point 408 _chemical_formula_moiety 'C9 H9 Cl N2' _chemical_formula_sum 'C9 H9 Cl N2' _chemical_formula_weight 180.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'F d d 2' _symmetry_space_group_name_Hall 'F 2 -2d' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 19.8523(3) _cell_length_b 39.3437(7) _cell_length_c 4.46970(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3491.12(11) _cell_formula_units_Z 16 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 35785 _cell_measurement_theta_min 2.07 _cell_measurement_theta_max 26.27 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 1.375 _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 3.392 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.447 _exptl_absorpt_correction_T_max 0.737 _exptl_absorpt_process_details ; Correction for absorption was made using XEMP (SHELXTL, Sheldrick (1990)). ; _exptl_special_details ; ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'multiwire proportional' _diffrn_measurement_method 'phi and omega 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 35785 _diffrn_reflns_av_R_equivalents 0.1654 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -48 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 4.50 _diffrn_reflns_theta_max 73.79 _reflns_number_total 1764 _reflns_number_gt 1704 _reflns_threshold_expression >2sigma(I) _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, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury (2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1278P)^2^+0.1073P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0009(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(3) _refine_ls_number_reflns 1764 _refine_ls_number_parameters 114 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0591 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1714 _refine_ls_wR_factor_gt 0.1695 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _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 Cl1 Cl 0.16497(4) 0.24642(2) 0.0212(4) 0.0973(5) Uani 1 1 d . . . N1 N 0.00180(10) 0.10797(6) 0.1797(6) 0.0629(6) Uani 1 1 d . . . H1 H -0.0441(19) 0.1202(10) 0.167(11) 0.090(12) Uiso 1 1 d . . . N3 N 0.10955(10) 0.11733(6) 0.3157(6) 0.0602(6) Uani 1 1 d . . . C7 C 0.10520(11) 0.18549(7) 0.0819(6) 0.0577(6) Uani 1 1 d . . . H7 H 0.1396 0.1806 0.2163 0.069 Uiso 1 1 calc R . . C8 C 0.10291(12) 0.21643(7) -0.0606(7) 0.0631(7) Uani 1 1 d . . . C9 C 0.05329(12) 0.22469(7) -0.2622(7) 0.0632(7) Uani 1 1 d . . . H9 H 0.0530 0.2458 -0.3567 0.076 Uiso 1 1 calc R . . C10 C 0.00354(13) 0.20082(9) -0.3213(7) 0.0652(7) Uani 1 1 d . . . H10 H -0.0306 0.2059 -0.4567 0.078 Uiso 1 1 calc R . . C11 C 0.00427(12) 0.16971(8) -0.1815(6) 0.0577(6) Uani 1 1 d . . . H11 H -0.0294 0.1539 -0.2224 0.069 Uiso 1 1 calc R . . C6 C 0.05536(10) 0.16163(6) 0.0222(6) 0.0508(6) Uani 1 1 d . . . C2 C 0.05724(10) 0.12859(7) 0.1789(5) 0.0508(6) Uani 1 1 d . . . C5 C 0.01548(13) 0.07979(9) 0.3802(8) 0.0703(8) Uani 1 1 d . . . H51 H 0.0060 0.0581 0.2851 0.084 Uiso 1 1 calc R . . H52 H -0.0107 0.0816 0.5629 0.084 Uiso 1 1 calc R . . C4 C 0.09088(12) 0.08396(8) 0.4419(9) 0.0684(8) Uani 1 1 d . . . H41 H 0.0997 0.0834 0.6553 0.082 Uiso 1 1 calc R . . H42 H 0.1163 0.0659 0.3464 0.082 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 0.0698(5) 0.0613(5) 0.1609(11) 0.0121(6) -0.0114(6) -0.0175(3) N1 0.0429(10) 0.0589(15) 0.0869(14) 0.0066(12) -0.0072(10) -0.0046(8) N3 0.0414(9) 0.0545(13) 0.0848(13) 0.0051(11) -0.0056(10) 0.0006(8) C7 0.0410(10) 0.0532(14) 0.0789(15) -0.0006(13) 0.0017(10) 0.0021(9) C8 0.0477(12) 0.0520(15) 0.0897(18) -0.0027(15) 0.0086(11) -0.0008(10) C9 0.0689(15) 0.0530(15) 0.0678(14) 0.0063(12) 0.0084(12) 0.0100(12) C10 0.0638(15) 0.0653(17) 0.0665(14) 0.0002(13) -0.0051(12) 0.0049(11) C11 0.0507(12) 0.0601(15) 0.0622(12) -0.0023(13) -0.0013(10) 0.0014(10) C6 0.0408(10) 0.0478(12) 0.0639(12) -0.0033(10) 0.0049(10) 0.0029(8) C2 0.0387(10) 0.0519(13) 0.0618(12) -0.0040(10) 0.0008(9) 0.0009(8) C5 0.0564(14) 0.0627(17) 0.092(2) 0.0102(16) -0.0017(13) -0.0079(12) C4 0.0575(14) 0.0575(18) 0.0903(18) 0.0104(15) -0.0016(13) 0.0020(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 C8 1.745(3) . ? N1 C2 1.367(3) . ? N1 C5 1.451(4) . ? N1 H1 1.03(4) . ? N3 C2 1.284(3) . ? N3 C4 1.476(4) . ? C7 C8 1.375(4) . ? C7 C6 1.390(3) . ? C7 H7 0.9300 . ? C8 C9 1.374(4) . ? C9 C10 1.389(4) . ? C9 H9 0.9300 . ? C10 C11 1.374(4) . ? C10 H10 0.9300 . ? C11 C6 1.400(4) . ? C11 H11 0.9300 . ? C6 C2 1.477(3) . ? C5 C4 1.531(3) . ? C5 H51 0.9700 . ? C5 H52 0.9700 . ? C4 H41 0.9700 . ? C4 H42 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 N1 C5 107.7(2) . . ? C2 N1 H1 116(2) . . ? C5 N1 H1 124(2) . . ? C2 N3 C4 106.6(2) . . ? C8 C7 C6 119.1(2) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C9 C8 C7 122.5(2) . . ? C9 C8 Cl1 118.9(2) . . ? C7 C8 Cl1 118.6(2) . . ? C8 C9 C10 118.3(3) . . ? C8 C9 H9 120.8 . . ? C10 C9 H9 120.8 . . ? C11 C10 C9 120.6(3) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C6 120.4(2) . . ? C10 C11 H11 119.8 . . ? C6 C11 H11 119.8 . . ? C7 C6 C11 119.2(2) . . ? C7 C6 C2 119.0(2) . . ? C11 C6 C2 121.8(2) . . ? N3 C2 N1 116.4(2) . . ? N3 C2 C6 123.4(2) . . ? N1 C2 C6 120.2(2) . . ? N1 C5 C4 102.2(2) . . ? N1 C5 H51 111.3 . . ? C4 C5 H51 111.3 . . ? N1 C5 H52 111.3 . . ? C4 C5 H52 111.3 . . ? H51 C5 H52 109.2 . . ? N3 C4 C5 105.8(2) . . ? N3 C4 H41 110.6 . . ? C5 C4 H41 110.6 . . ? N3 C4 H42 110.6 . . ? C5 C4 H42 110.6 . . ? H41 C4 H42 108.7 . . ? 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 C6 C7 C8 C9 -0.4(4) . . . . ? C6 C7 C8 Cl1 178.9(2) . . . . ? C7 C8 C9 C10 0.4(4) . . . . ? Cl1 C8 C9 C10 -178.9(2) . . . . ? C8 C9 C10 C11 -0.1(4) . . . . ? C9 C10 C11 C6 -0.2(4) . . . . ? C8 C7 C6 C11 0.1(4) . . . . ? C8 C7 C6 C2 -179.1(2) . . . . ? C10 C11 C6 C7 0.2(4) . . . . ? C10 C11 C6 C2 179.3(2) . . . . ? C4 N3 C2 N1 -1.2(3) . . . . ? C4 N3 C2 C6 179.8(2) . . . . ? C5 N1 C2 N3 8.1(3) . . . . ? C5 N1 C2 C6 -172.8(2) . . . . ? C7 C6 C2 N3 -16.2(4) . . . . ? C11 C6 C2 N3 164.6(3) . . . . ? C7 C6 C2 N1 164.8(3) . . . . ? C11 C6 C2 N1 -14.3(3) . . . . ? C2 N1 C5 C4 -10.7(3) . . . . ? C2 N3 C4 C5 -5.8(3) . . . . ? N1 C5 C4 N3 9.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 73.79 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.233 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.058 #AND data_1.2GPa _database_code_depnum_ccdc_archive 'CCDC 872963' #TrackingRef '- IMDZLNall.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic 2-(3-chlorophenyl)-imidazoline _chemical_name_common 2-(3-chlorophenyl)-imidazoline _chemical_melting_point 408 _chemical_formula_moiety 'C9 H9 Cl N2' _chemical_formula_sum 'C9 H9 Cl N2' _chemical_formula_weight 180.63 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'F d d 2' _symmetry_space_group_name_Hall 'F 2 -2d' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 19.659(9) _cell_length_b 38.94(4) _cell_length_c 4.070(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3115(5) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_pressure 1200000 _cell_measurement_reflns_used 373 _cell_measurement_theta_min 4.65 _cell_measurement_theta_max 24.68 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas 1.540 _exptl_crystal_density_diffrn 1.540 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.424 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.4911 _exptl_absorpt_correction_T_max 0.8528 _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 Data were collected at room temperature and pressure of 1.20(5) GPa (1200000 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 16.4 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 2892 _diffrn_reflns_av_R_equivalents 0.3073 _diffrn_reflns_av_sigmaI/netI 0.2401 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 4.65 _diffrn_reflns_theta_max 24.68 _reflns_number_total 373 _reflns_number_gt 250 _reflns_threshold_expression >2sigma(I) _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, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 2008' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1063P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.8(7) _refine_ls_number_reflns 373 _refine_ls_number_parameters 33 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1802 _refine_ls_R_factor_gt 0.1266 _refine_ls_wR_factor_ref 0.2861 _refine_ls_wR_factor_gt 0.2628 _refine_ls_goodness_of_fit_ref 1.224 _refine_ls_restrained_S_all 1.222 _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 Cl1 Cl 0.1680(2) 0.2445(6) 0.043(2) 0.036(16) Uani 1 1 d . . . N1 N -0.0006(8) 0.1048(15) 0.169(4) 0.010(4) Uiso 1 1 d . . . H1 H -0.0402 0.1087 0.0871 0.012 Uiso 1 1 calc R . . N3 N 0.1067(7) 0.1105(15) 0.331(3) 0.010(4) Uiso 1 1 d . . . C7 C 0.1057(6) 0.1857(8) 0.081(2) 0.009(2) Uiso 1 1 d G . . H7 H 0.1411 0.1792 0.2194 0.011 Uiso 1 1 calc R . . C8 C 0.1046(6) 0.2186(8) -0.052(3) 0.009(2) Uiso 1 1 d G . . C9 C 0.0518(7) 0.2283(8) -0.260(3) 0.009(2) Uiso 1 1 d G . . H9 H 0.0510 0.2503 -0.3488 0.011 Uiso 1 1 calc R . . C10 C 0.0002(6) 0.2052(8) -0.334(3) 0.009(2) Uiso 1 1 d G . . H10 H -0.0352 0.2117 -0.4724 0.011 Uiso 1 1 calc R . . C11 C 0.0013(6) 0.1724(8) -0.200(3) 0.009(2) Uiso 1 1 d G . . H11 H -0.0332 0.1569 -0.2500 0.011 Uiso 1 1 calc R . . C6 C 0.0541(7) 0.1626(8) 0.007(3) 0.009(2) Uiso 1 1 d G . . C2 C 0.0525(10) 0.133(2) 0.166(4) 0.009(2) Uiso 1 1 d . . . C5 C 0.0163(8) 0.068(2) 0.325(6) 0.009(2) Uiso 1 1 d . . . H51 H 0.0174 0.0498 0.1578 0.011 Uiso 1 1 calc R . . H52 H -0.0161 0.0613 0.4942 0.011 Uiso 1 1 calc R . . C4 C 0.0959(9) 0.0751(19) 0.486(5) 0.009(2) Uiso 1 1 d . . . H41 H 0.0955 0.0760 0.7240 0.011 Uiso 1 1 calc R . . H42 H 0.1292 0.0585 0.4117 0.011 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 0.017(3) 0.04(5) 0.052(4) 0.031(10) -0.008(4) -0.003(7) _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 C8 1.65(2) . ? N1 C5 1.62(9) . ? N1 C2 1.51(7) . ? N3 C2 1.53(5) . ? N3 C4 1.53(8) . ? C7 C8 1.3900 . ? C7 C6 1.3900 . ? C8 C9 1.3900 . ? C9 C10 1.3900 . ? C10 C11 1.3900 . ? C11 C6 1.3900 . ? C6 C2 1.34(7) . ? C5 C4 1.72(3) . ? 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 C5 N1 C2 120(2) . . ? C2 N3 C4 126(3) . . ? C8 C7 C6 120.0 . . ? C9 C8 C7 120.0 . . ? C9 C8 Cl1 122.8(13) . . ? C7 C8 Cl1 117.2(13) . . ? C10 C9 C8 120.0 . . ? C9 C10 C11 120.0 . . ? C10 C11 C6 120.0 . . ? C11 C6 C7 120.0 . . ? C11 C6 C2 121.0(16) . . ? C7 C6 C2 118.6(17) . . ? N3 C2 C6 134(3) . . ? N3 C2 N1 94(4) . . ? C6 C2 N1 131(2) . . ? N1 C5 C4 100(4) . . ? N3 C4 C5 97(3) . . ? _diffrn_measured_fraction_theta_max 0.270 _diffrn_reflns_theta_full 24.68 _diffrn_measured_fraction_theta_full 0.270 _refine_diff_density_max 0.427 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.094 #END