# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics # This journal is © The Owner Societies 2011 data_global _journal_name_full Phys.Chem.Chem.Phys.(PCCP) _journal_coden_Cambridge 1326 _publ_contact_author_name 'Katrusiak, Andrzej' _publ_contact_author_email katran@amu.edu.pl _publ_section_title ; Pressure-induced pseudorotation in crystalline pyrrolidine ; loop_ _publ_author_name K.Dziubek A.Katrusiak # Attachment '- pyrrolidine.cif' data_pyrrolidine_100K _database_code_depnum_ccdc_archive 'CCDC 809513' #TrackingRef '- pyrrolidine.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; azacyclopentane ; _chemical_name_common pyrrolidine _chemical_melting_point 210.15 _chemical_formula_moiety 'C4 H9 N' _chemical_formula_sum 'C4 H9 N' _chemical_formula_weight 71.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' 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 8.6367(6) _cell_length_b 5.2081(3) _cell_length_c 10.6375(8) _cell_angle_alpha 90.00 _cell_angle_beta 110.579(8) _cell_angle_gamma 90.00 _cell_volume 447.95(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2331 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 28.96 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_size_rad 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.055 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 160 _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Crystal grown in situ in 0.3 mm glass capillary at 210 K. ; _diffrn_ambient_temperature 100(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 '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 4396 _diffrn_reflns_av_R_equivalents 0.0142 _diffrn_reflns_av_sigmaI/netI 0.0137 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 29.68 _reflns_number_total 1184 _reflns_number_gt 987 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction, 2010)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction, 2010)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction, 2010)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _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^)+(0.0619P)^2^+0.0671P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1184 _refine_ls_number_parameters 73 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.1050 _refine_ls_wR_factor_gt 0.0986 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 N1 N 0.39491(9) 1.02004(15) 0.19553(8) 0.0239(2) Uani 1 1 d . . . H1 H 0.4653(14) 0.900(2) 0.2401(12) 0.029 Uiso 1 1 d . . . C2 C 0.31271(11) 0.92731(18) 0.05759(9) 0.0254(2) Uani 1 1 d . . . H21 H 0.3931(14) 0.855(2) 0.0224(12) 0.030 Uiso 1 1 d . . . H22 H 0.2563(14) 1.073(2) -0.0007(12) 0.030 Uiso 1 1 d . . . C3 C 0.18469(11) 0.72573(18) 0.06291(9) 0.0254(2) Uani 1 1 d . . . H31 H 0.0858(14) 0.727(2) -0.0162(12) 0.030 Uiso 1 1 d . . . H32 H 0.2292(15) 0.555(2) 0.0649(12) 0.030 Uiso 1 1 d . . . C4 C 0.15009(12) 0.79056(19) 0.19162(10) 0.0273(2) Uani 1 1 d . . . H41 H 0.1827(14) 0.647(3) 0.2553(12) 0.033 Uiso 1 1 d . . . H42 H 0.0311(15) 0.823(2) 0.1738(12) 0.033 Uiso 1 1 d . . . C5 C 0.26081(12) 1.02344(17) 0.25068(10) 0.0269(2) Uani 1 1 d . . . H51 H 0.1958(15) 1.182(3) 0.2221(13) 0.032 Uiso 1 1 d . . . H52 H 0.3066(15) 1.025(2) 0.3495(13) 0.032 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 N1 0.0210(4) 0.0206(4) 0.0276(4) -0.0012(3) 0.0051(3) -0.0017(3) C2 0.0279(4) 0.0255(5) 0.0258(4) -0.0019(3) 0.0134(4) -0.0078(3) C3 0.0273(4) 0.0251(5) 0.0236(4) -0.0019(3) 0.0090(4) -0.0090(3) C4 0.0304(5) 0.0239(4) 0.0335(5) 0.0003(4) 0.0185(4) -0.0038(3) C5 0.0376(5) 0.0184(4) 0.0287(5) -0.0015(3) 0.0167(4) -0.0006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.4690(12) . n N1 C5 1.4708(12) . n C2 C3 1.5401(12) . n C3 C4 1.5380(13) . n C4 C5 1.5355(13) . n 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 103.33(7) . . n N1 C2 C3 106.77(7) . . n C4 C3 C2 104.46(7) . . n C5 C4 C3 104.46(7) . . n N1 C5 C4 106.96(7) . . n _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 29.68 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 0.299 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.034 # AND data_pyrrolidine_200K _database_code_depnum_ccdc_archive 'CCDC 809514' #TrackingRef '- pyrrolidine.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; azacyclopentane ; _chemical_name_common pyrrolidine _chemical_melting_point 210.15 _chemical_formula_moiety 'C4 H9 N' _chemical_formula_sum 'C4 H9 N' _chemical_formula_weight 71.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' 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 8.717(2) _cell_length_b 5.2330(10) _cell_length_c 10.831(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.45(3) _cell_angle_gamma 90.00 _cell_volume 462.93(19) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 2296 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 27.05 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_size_rad 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.020 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 160 _exptl_absorpt_coefficient_mu 0.062 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Crystal grown in situ in 0.3 mm glass capillary at 210 K. ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _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 2975 _diffrn_reflns_av_R_equivalents 0.0722 _diffrn_reflns_av_sigmaI/netI 0.0629 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 29.80 _reflns_number_total 1187 _reflns_number_gt 712 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction, 2010)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction, 2010)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction, 2010)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _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^)+(0.2000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1187 _refine_ls_number_parameters 73 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1047 _refine_ls_R_factor_gt 0.0629 _refine_ls_wR_factor_ref 0.2815 _refine_ls_wR_factor_gt 0.1892 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 N1 N 0.3921(2) 1.0242(3) 0.19653(19) 0.0496(6) Uani 1 1 d . . . H1 H 0.456(3) 0.909(5) 0.235(3) 0.060 Uiso 1 1 d . . . C2 C 0.3109(3) 0.9330(4) 0.0621(2) 0.0522(7) Uani 1 1 d . . . H21 H 0.379(3) 0.876(6) 0.025(3) 0.063 Uiso 1 1 d . . . H22 H 0.253(3) 1.082(5) 0.002(3) 0.063 Uiso 1 1 d . . . C3 C 0.1896(3) 0.7291(5) 0.0676(2) 0.0521(7) Uani 1 1 d . . . H31 H 0.097(3) 0.738(5) -0.004(3) 0.062 Uiso 1 1 d . . . H32 H 0.235(3) 0.569(6) 0.068(3) 0.062 Uiso 1 1 d . . . C4 C 0.1550(3) 0.7880(5) 0.1928(2) 0.0571(7) Uani 1 1 d . . . H41 H 0.194(3) 0.647(6) 0.255(3) 0.068 Uiso 1 1 d . . . H42 H 0.055(4) 0.814(5) 0.188(3) 0.068 Uiso 1 1 d . . . C5 C 0.2630(3) 1.0171(4) 0.2528(3) 0.0583(8) Uani 1 1 d . . . H51 H 0.195(4) 1.163(6) 0.223(3) 0.070 Uiso 1 1 d . . . H52 H 0.300(4) 1.019(5) 0.344(4) 0.070 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 N1 0.0426(10) 0.0403(10) 0.0567(12) -0.0008(7) 0.0056(8) -0.0032(6) C2 0.0571(13) 0.0524(13) 0.0510(12) -0.0014(10) 0.0239(10) -0.0105(10) C3 0.0545(12) 0.0484(13) 0.0489(12) -0.0026(9) 0.0127(10) -0.0139(10) C4 0.0597(13) 0.0513(13) 0.0682(15) 0.0028(10) 0.0324(12) -0.0076(10) C5 0.0800(17) 0.0415(14) 0.0585(15) -0.0024(9) 0.0306(13) -0.0033(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 N1 C5 1.456(3) . n N1 C2 1.459(3) . n C2 C3 1.518(3) . n C3 C4 1.519(3) . n C4 C5 1.522(3) . n 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 103.48(17) . . n N1 C2 C3 106.96(17) . . n C2 C3 C4 104.53(18) . . n C3 C4 C5 104.77(18) . . n N1 C5 C4 107.11(19) . . n _diffrn_measured_fraction_theta_max 0.895 _diffrn_reflns_theta_full 29.80 _diffrn_measured_fraction_theta_full 0.895 _refine_diff_density_max 0.224 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.074 # AND data_pyrrolidine_15_kbar _database_code_depnum_ccdc_archive 'CCDC 809515' #TrackingRef '- pyrrolidine.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; azacyclopentane ; _chemical_name_common pyrrolidine _chemical_melting_point 210.15 _chemical_formula_moiety 'C4 H9 N' _chemical_formula_sum 'C4 H9 N' _chemical_formula_weight 71.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.702(2) _cell_length_b 4.9380(10) _cell_length_c 10.572(2) _cell_angle_alpha 94.37(3) _cell_angle_beta 98.54(3) _cell_angle_gamma 99.59(3) _cell_volume 389.96(15) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 666 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 25.37 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.12 _exptl_crystal_size_rad 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.211 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 160 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.438 _exptl_absorpt_correction_T_max 0.826 _exptl_absorpt_process_details ; Corrections for absorption of the diamond-anvil cell and the sample were made using program REDSHADE [Katrusiak, A. (2003) REDSHADE. Adam Mickiewicz University Pozna\'n; Katrusiak, A. (2004) Z. Kristallogr. 219, 461-467]. ; _exptl_special_details ; Data were collected at room temperature and pressure of 1.50(5) GPa on a crystal obtained by the high-pressure in-situ crystallization technique. Pressure was calibrated by monitoring the shift of the R1 ruby fluorescence line. [Piermarini, G. J., Block, S., Barnett, J. D., Forman, R. A. (1975) J. Appl. Phys. 46, 2774-2780]. ; _diffrn_ambient_temperature 295(2) _diffrn_ambient_environment 'diamond-anvil cell' _diffrn_ambient_pressure 1500000 _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 2002 _diffrn_reflns_av_R_equivalents 0.0848 _diffrn_reflns_av_sigmaI/netI 0.1053 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 24.88 _reflns_number_total 434 _reflns_number_gt 259 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction, 2010)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction, 2010)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction, 2010); REDSHADE (Katrusiak, A. 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _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^)+(0.0903P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 434 _refine_ls_number_parameters 47 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1324 _refine_ls_R_factor_gt 0.0764 _refine_ls_wR_factor_ref 0.1920 _refine_ls_wR_factor_gt 0.1652 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 N1 N 0.3182(7) 1.1601(16) 0.226(2) 0.030(2) Uiso 1 1 d . . . H1 H 0.388(8) 1.057(14) 0.239(14) 0.036 Uiso 1 1 d . . . C2 C 0.3360(11) 1.120(2) 0.094(3) 0.047(3) Uiso 1 1 d . . . H21 H 0.4613 1.1418 0.0860 0.056 Uiso 1 1 calc R . . H22 H 0.2846 1.2564 0.0469 0.056 Uiso 1 1 calc R . . C3 C 0.2399(9) 0.8283(16) 0.0365(19) 0.042(2) Uiso 1 1 d . . . H32 H 0.3229 0.7010 0.0342 0.051 Uiso 1 1 calc R . . H31 H 0.1758 0.8299 -0.0496 0.051 Uiso 1 1 calc R . . C4 C 0.1096(9) 0.7535(18) 0.1329(19) 0.042(2) Uiso 1 1 d . . . H42 H -0.0128 0.7130 0.0884 0.050 Uiso 1 1 calc R . . H41 H 0.1356 0.5925 0.1740 0.050 Uiso 1 1 calc R . . C5 C 0.1359(9) 1.0003(18) 0.232(2) 0.047(2) Uiso 1 1 d . . . H51 H 0.0453 1.1120 0.2112 0.056 Uiso 1 1 calc R . . H52 H 0.1298 0.9418 0.3168 0.056 Uiso 1 1 calc R . . N6 N 0.5548(8) 0.7488(13) 0.3181(14) 0.0312(17) Uiso 1 1 d . . . H6 H 0.470(8) 0.607(15) 0.312(14) 0.037 Uiso 1 1 d . . . C7 C 0.6454(9) 0.7915(19) 0.454(2) 0.042(2) Uiso 1 1 d . . . H71 H 0.5615 0.7328 0.5107 0.050 Uiso 1 1 calc R . . H72 H 0.6963 0.9850 0.4784 0.050 Uiso 1 1 calc R . . C8 C 0.7947(10) 0.6146(18) 0.463(2) 0.032(2) Uiso 1 1 d . . . H81 H 0.9106 0.7289 0.4941 0.039 Uiso 1 1 calc R . . H82 H 0.7732 0.4719 0.5194 0.039 Uiso 1 1 calc R . . C9 C 0.7860(10) 0.492(2) 0.329(2) 0.043(3) Uiso 1 1 d . . . H91 H 0.7218 0.3027 0.3161 0.051 Uiso 1 1 calc R . . H92 H 0.9044 0.4959 0.3075 0.051 Uiso 1 1 calc R . . C10 C 0.6842(9) 0.6808(18) 0.250(2) 0.039(2) Uiso 1 1 d . . . H101 H 0.7650 0.8462 0.2381 0.047 Uiso 1 1 calc R . . H102 H 0.6295 0.5862 0.1665 0.047 Uiso 1 1 calc R . . _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 N1 C2 1.43(3) . n N1 C5 1.502(11) . n C2 C3 1.537(17) . n C3 C4 1.56(2) . n C4 C5 1.51(2) . n N6 C10 1.38(2) . n N6 C7 1.48(3) . n C7 C8 1.552(13) . n C8 C9 1.48(3) . n C9 C10 1.533(13) . n 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 104.0(12) . . n N1 C2 C3 109.7(13) . . n C2 C3 C4 101.7(16) . . n C5 C4 C3 107.0(9) . . n N1 C5 C4 105.4(13) . . n C10 N6 C7 103.8(7) . . n N6 C7 C8 106.4(18) . . n C9 C8 C7 104.7(14) . . n C8 C9 C10 102.3(13) . . n N6 C10 C9 107.2(17) . . n _diffrn_measured_fraction_theta_max 0.321 _diffrn_reflns_theta_full 24.88 _diffrn_measured_fraction_theta_full 0.321 _refine_diff_density_max 0.123 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.034 # END