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 ; Pressure induced transformations of 1,4-diazabicyclo[2.2.2]octane (dabco) hydroiodide: diprotonation of dabco, its N-methylation and cocrystallization with methanol ; loop_ _publ_author_name 'Andrzej Katrusiak' 'Anna Olejniczak' # Attachment '18.txt' data_dabcoHI18 _database_code_depnum_ccdc_archive 'CCDC 762327' #TrackingRef '18.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4-diazabicyclo[2.2.2]octane dihydroiodide trimethanol cocrystal ; _chemical_name_common ;1,4-diazabicyclo(2.2.2)octane dihydroiodide trimethanol cocrystal ; _chemical_melting_point ? _chemical_formula_moiety 'C6 H14 N2, 3(C H4 O), 2(I)' _chemical_formula_sum 'C9 H26 I2 N2 O3' _chemical_formula_weight 464.12 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/m' _symmetry_space_group_name_Hall '-P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 7.385(3) _cell_length_b 7.782(5) _cell_length_c 12.82(8) _cell_angle_alpha 90.00 _cell_angle_beta 95.02(12) _cell_angle_gamma 90.00 _cell_volume 734(5) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_pressure 1800000 _cell_measurement_reflns_used 639 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 28.98 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.101 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 4.284 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.52 _exptl_absorpt_correction_T_max 0.69 _exptl_absorpt_process_details ; Katrusiak, A. (2003). REDSHABS - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Pozna\'n. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 ; _exptl_special_details ; Data were collected at room temperature and pressure of 1.80(5) GPa (1800000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line. ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD \k geometry' _diffrn_measurement_method ;HP omega scans - for more details see: A. Budzianowski, A. Katrusiak in High-Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168 ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 639 _diffrn_reflns_av_R_equivalents 0.0847 _diffrn_reflns_av_sigmaI/netI 0.0951 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 28.92 _reflns_number_total 281 _reflns_number_gt 195 _reflns_threshold_expression >2sigma(I) _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^)+(0.0316P)^2^+23.9176P] 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 281 _refine_ls_number_parameters 47 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.1172 _refine_ls_R_factor_gt 0.0617 _refine_ls_wR_factor_ref 0.1682 _refine_ls_wR_factor_gt 0.1424 _refine_ls_goodness_of_fit_ref 1.386 _refine_ls_restrained_S_all 1.374 _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 I1 I 0.7121(4) 0.2500 0.9911(11) 0.036(12) Uani 1 2 d S . . I2 I 0.1252(5) -0.2500 0.6121(11) 0.030(14) Uani 1 2 d S . . N1 N 0.341(6) 0.2500 0.759(7) 0.025(11) Uiso 1 2 d SD . . H1 H 0.4629 0.2500 0.7539 0.030 Uiso 1 2 calc SR . . C3 C 0.291(4) 0.093(4) 0.809(7) 0.026(9) Uiso 1 1 d D . . H3A H 0.3626 0.0806 0.8754 0.032 Uiso 1 1 calc R . . H3B H 0.3176 -0.0044 0.7652 0.032 Uiso 1 1 calc R . . N2 N 0.005(4) 0.2500 0.772(8) 0.010(9) Uiso 1 2 d SD . . H2 H -0.1176 0.2500 0.7753 0.012 Uiso 1 2 calc SR . . C4 C 0.080(3) 0.091(4) 0.828(7) 0.021(8) Uiso 1 1 d D . . H4A H 0.0217 -0.0119 0.7980 0.025 Uiso 1 1 calc R . . H4B H 0.0638 0.0955 0.9017 0.025 Uiso 1 1 calc R . . C2 C 0.040(6) 0.2500 0.660(9) 0.042(18) Uiso 1 2 d SD . . H2A H -0.0134 0.3511 0.6253 0.050 Uiso 0.50 1 calc PR . . H2B H -0.0134 0.1489 0.6253 0.050 Uiso 0.50 1 calc PR . . C1 C 0.247(6) 0.2500 0.653(8) 0.032(15) Uiso 1 2 d SD . . H1A H 0.2824 0.1490 0.6152 0.038 Uiso 0.50 1 calc PR . . H1B H 0.2824 0.3510 0.6152 0.038 Uiso 0.50 1 calc PR . . O11 O 0.656(3) 0.050(3) 0.707(6) 0.022(6) Uiso 1 1 d D . . H11 H 0.6705 -0.0322 0.7476 0.027 Uiso 1 1 calc R . . C11 C 0.621(5) -0.017(7) 0.593(7) 0.055(16) Uiso 1 1 d D . . H11A H 0.4928 -0.0342 0.5761 0.066 Uiso 1 1 calc R . . H11B H 0.6834 -0.1243 0.5857 0.066 Uiso 1 1 calc R . . H11C H 0.6646 0.0655 0.5453 0.066 Uiso 1 1 calc R . . O12 O 0.606(5) -0.2500 0.821(9) 0.033(10) Uiso 1 2 d S . . H12 H 0.5193 -0.2500 0.8569 0.040 Uiso 1 2 calc SR . . C12 C 0.761(8) -0.2500 0.884(19) 0.08(3) Uiso 1 2 d S . . H12A H 0.8627 -0.2500 0.8424 0.096 Uiso 1 2 calc SR . . H12B H 0.7654 -0.3507 0.9275 0.096 Uiso 0.50 1 calc PR . . H12C H 0.7654 -0.1493 0.9275 0.096 Uiso 0.50 1 calc PR . . 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 I1 0.0217(17) 0.024(2) 0.06(4) 0.000 0.006(6) 0.000 I2 0.036(2) 0.022(3) 0.03(4) 0.000 0.005(8) 0.000 _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 C3 1.44(5) . ? N1 C3 1.44(5) 4_565 ? N1 C1 1.47(5) . ? N1 H1 0.9100 . ? C3 C4 1.59(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? N2 C2 1.48(5) . ? N2 C4 1.51(4) 4_565 ? N2 C4 1.51(4) . ? N2 H2 0.9100 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C2 C1 1.54(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? O11 C11 1.56(5) . ? O11 H11 0.8200 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? O12 C12 1.34(16) . ? O12 H12 0.8200 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? 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 C3 N1 C3 116(7) . 4_565 ? C3 N1 C1 107(5) . . ? C3 N1 C1 107(5) 4_565 . ? C3 N1 H1 108.9 . . ? C3 N1 H1 108.9 4_565 . ? C1 N1 H1 108.9 . . ? N1 C3 C4 111(3) . . ? N1 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? N1 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? C2 N2 C4 112(4) . 4_565 ? C2 N2 C4 112(4) . . ? C4 N2 C4 110(6) 4_565 . ? C2 N2 H2 107.8 . . ? C4 N2 H2 107.8 4_565 . ? C4 N2 H2 107.8 . . ? N2 C4 C3 104(3) . . ? N2 C4 H4A 110.9 . . ? C3 C4 H4A 110.9 . . ? N2 C4 H4B 110.9 . . ? C3 C4 H4B 110.9 . . ? H4A C4 H4B 108.9 . . ? N2 C2 C1 108(6) . . ? N2 C2 H2A 110.0 . . ? C1 C2 H2A 110.0 . . ? N2 C2 H2B 110.0 . . ? C1 C2 H2B 110.0 . . ? H2A C2 H2B 108.4 . . ? N1 C1 C2 110(6) . . ? N1 C1 H1A 109.7 . . ? C2 C1 H1A 109.7 . . ? N1 C1 H1B 109.7 . . ? C2 C1 H1B 109.7 . . ? H1A C1 H1B 108.2 . . ? C11 O11 H11 109.5 . . ? O11 C11 H11A 109.5 . . ? O11 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O11 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C12 O12 H12 109.5 . . ? O12 C12 H12A 109.5 . . ? O12 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O12 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.135 _diffrn_reflns_theta_full 28.92 _diffrn_measured_fraction_theta_full 0.135 _refine_diff_density_max 0.625 _refine_diff_density_min -0.672 _refine_diff_density_rms 0.159 # Attachment '24.txt' data_dabcoHI24 _database_code_depnum_ccdc_archive 'CCDC 762328' #TrackingRef '24.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-methyl-1,4-diazabicyclo[2.2.2]octanium iodide dimethanol cocrystal ; _chemical_name_common ;N-methyl-1,4-diazabicyclo(2.2.2)octanium iodide dimethanol cocrystal ; _chemical_melting_point ? _chemical_formula_moiety 'C7 H15 N2, 2(C H4 O), I' _chemical_formula_sum 'C9 H23 I N2 O2' _chemical_formula_weight 318.19 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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/m' _symmetry_space_group_name_Hall '-P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 8.88(2) _cell_length_b 6.5844(4) _cell_length_c 10.335(10) _cell_angle_alpha 90.00 _cell_angle_beta 108.69(19) _cell_angle_gamma 90.00 _cell_volume 572.6(15) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_pressure 2400000 _cell_measurement_reflns_used 3760 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 29.22 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.845 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 2.777 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.59 _exptl_absorpt_correction_T_max 0.80 _exptl_absorpt_process_details ; Katrusiak, A. (2003). REDSHABS - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Pozna\'n. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 ; _exptl_special_details ; Data were collected at room temperature and pressure of 2.40(5) GPa (2400000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line. ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD \k geometry' _diffrn_measurement_method ;HP omega scans - for more details see: A. Budzianowski, A. Katrusiak in High-Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168 ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3760 _diffrn_reflns_av_R_equivalents 0.0683 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 29.20 _reflns_number_total 328 _reflns_number_gt 322 _reflns_threshold_expression >2sigma(I) _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^)+(0.0436P)^2^+2.8141P] 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 328 _refine_ls_number_parameters 42 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.0903 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.088 _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 I1 I 0.1700(4) 0.2500 0.28237(19) 0.039(4) Uani 1 2 d S . . N1 N 0.417(6) 0.2500 -0.119(3) 0.025(2) Uiso 1 2 d SD . . N2 N 0.147(5) 0.2500 -0.300(3) 0.018(2) Uiso 1 2 d SD . . C2 C 0.145(5) 0.2500 -0.154(3) 0.025(3) Uiso 1 2 d SD . . H2A H 0.0867 0.3689 -0.1409 0.030 Uiso 0.50 1 calc PR . . H2B H 0.0867 0.1311 -0.1409 0.030 Uiso 0.50 1 calc PR . . C1 C 0.306(5) 0.2500 -0.047(3) 0.025(3) Uiso 1 2 d SD . . H1A H 0.3197 0.3697 0.0099 0.030 Uiso 0.50 1 calc PR . . H1B H 0.3197 0.1303 0.0099 0.030 Uiso 0.50 1 calc PR . . C3 C 0.401(3) 0.0673(11) -0.2049(19) 0.0221(19) Uiso 1 1 d D . . H3A H 0.4848 0.0661 -0.2463 0.026 Uiso 1 1 calc R . . H3B H 0.4125 -0.0532 -0.1486 0.026 Uiso 1 1 calc R . . C4 C 0.245(3) 0.0640(12) -0.3126(19) 0.025(2) Uiso 1 1 d D . . H4A H 0.1888 -0.0589 -0.3047 0.030 Uiso 1 1 calc R . . H4B H 0.2604 0.0639 -0.4015 0.030 Uiso 1 1 calc R . . O11 O 0.584(4) 0.2500 0.406(2) 0.036(2) Uiso 1 2 d S . . H11 H 0.4906 0.2500 0.3570 0.044 Uiso 1 2 calc SR . . C11 C 0.589(6) 0.2500 0.546(3) 0.035(3) Uiso 1 2 d S . . H11A H 0.4830 0.2500 0.5505 0.042 Uiso 1 2 calc SR . . H11B H 0.6443 0.3690 0.5904 0.042 Uiso 0.50 1 calc PR . . H11C H 0.6443 0.1310 0.5904 0.042 Uiso 0.50 1 calc PR . . O12 O 0.730(5) 0.2500 0.039(3) 0.034(2) Uiso 1 2 d S . . H12 H 0.6364 0.2500 -0.0085 0.041 Uiso 1 2 calc SR . . C12 C 0.828(5) 0.2500 -0.048(3) 0.033(3) Uiso 1 2 d S . . H12A H 0.7614 0.2500 -0.1414 0.039 Uiso 1 2 calc SR . . H12B H 0.8935 0.1310 -0.0296 0.039 Uiso 0.50 1 calc PR . . H12C H 0.8935 0.3690 -0.0296 0.039 Uiso 0.50 1 calc PR . . C5 C 0.015(8) 0.2500 -0.397(4) 0.030(4) Uiso 1 2 d S . . H5A H 0.0347 0.2500 -0.4831 0.036 Uiso 1 2 calc SR . . H5B H -0.0444 0.3690 -0.3905 0.036 Uiso 0.50 1 calc PR . . H5C H -0.0444 0.1310 -0.3905 0.036 Uiso 0.50 1 calc PR . . 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 I1 0.052(10) 0.0284(4) 0.038(3) 0.000 0.018(6) 0.000 _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 C1 1.41(3) . ? N1 C3 1.475(16) . ? N1 C3 1.475(16) 4_565 ? N2 C5 1.28(8) . ? N2 C2 1.51(2) . ? N2 C4 1.53(3) 4_565 ? N2 C4 1.53(3) . ? C2 C1 1.50(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C3 C4 1.47(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? O11 C11 1.42(2) . ? O11 H11 0.8200 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? O12 C12 1.43(3) . ? O12 H12 0.8200 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? 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 N1 C3 112(2) . . ? C1 N1 C3 112(2) . 4_565 ? C3 N1 C3 109.3(17) . 4_565 ? C5 N2 C2 119(3) . . ? C5 N2 C4 109.8(17) . 4_565 ? C2 N2 C4 106.0(19) . 4_565 ? C5 N2 C4 109.8(17) . . ? C2 N2 C4 106.0(19) . . ? C4 N2 C4 106(3) 4_565 . ? C1 C2 N2 114(3) . . ? C1 C2 H2A 108.6 . . ? N2 C2 H2A 108.6 . . ? C1 C2 H2B 108.6 . . ? N2 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? N1 C1 C2 106(2) . . ? N1 C1 H1A 110.5 . . ? C2 C1 H1A 110.5 . . ? N1 C1 H1B 110.5 . . ? C2 C1 H1B 110.5 . . ? H1A C1 H1B 108.7 . . ? C4 C3 N1 111(2) . . ? C4 C3 H3A 109.5 . . ? N1 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C3 C4 N2 110.3(19) . . ? C3 C4 H4A 109.6 . . ? N2 C4 H4A 109.6 . . ? C3 C4 H4B 109.6 . . ? N2 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C11 O11 H11 109.5 . . ? O11 C11 H11A 109.5 . . ? O11 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O11 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C12 O12 H12 109.5 . . ? O12 C12 H12A 109.5 . . ? O12 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O12 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C5 H5A 109.5 . . ? N2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.196 _diffrn_reflns_theta_full 29.20 _diffrn_measured_fraction_theta_full 0.196 _refine_diff_density_max 0.296 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.074