# 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 ? loop_ _publ_author_name _publ_author_footnote _publ_author_address 'W. Nowicki' ; ? ; ; ? ; 'A. Olejniczak' '' '' 'M. Andrzejewski' '' '' 'A. Katrusiak' '' '' _publ_contact_author_address # Address of author for correspondence ; ? ; _publ_contact_author_email katran@amu.edu.pl _publ_contact_author_fax ? _publ_contact_author_phone ? #============================================================================= #============================================================================= # 1. SUBMISSION DETAILS _publ_contact_author_name 'Andrzej Katrusiak' # Name of author for correspondence _publ_contact_letter ; ? ; _publ_requested_category ? # Acta C: one of CI/CM/CO/FI/FM/FO _publ_requested_coeditor_name ? #============================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; 'dab' ; data_1 _database_code_depnum_ccdc_archive 'CCDC 860848' # Definition of non standard CIF items (Reliability indices used in FULLPROF) loop_ _publ_manuscript_incl_extra_item _publ_manuscript_incl_extra_info _publ_manuscript_incl_extra_defn # Name Explanation Standard? # ------ ----------- --------- '_pd_proc_ls_prof_cR_factor' 'Prof. R-factor CORRECTED for background' no '_pd_proc_ls_prof_cwR_factor' 'wProf.R-factor CORRECTED for background' no '_pd_proc_ls_prof_cwR_expected' 'wProf.Expected CORRECTED for background' no '_pd_proc_ls_prof_chi2' 'Chi-square for all considered points' no '_pd_proc_ls_prof_echi2' 'Chi-2 for points with Bragg contribution' no _publ_section_title_footnote ; ; #============================================================================= # 4. TEXT _publ_section_synopsis ; ? ; _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_exptl_prep # Details of the preparation of the sample(s) # should be given here. ; ? ; _publ_section_exptl_refinement ; ? ; _publ_section_references ; ? ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ; #============================================================================= #============================================================================= # If more than one structure is reported, the remaining sections should be # completed per structure. For each data set, replace the '?' in the # data_? line below by a unique identifier. _diffrn_radiation_wavelength 0.5385(1) #============================================================================= # 5. CHEMICAL DATA _chemical_name_systematic '1,4-diazabicyclo(2.2.2)octane hydrobromide' _chemical_name_common ? _chemical_formula_moiety 'C6 H13 N2, Br' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_sum 'C6 H13 Br N2' _chemical_formula_weight 193.08 _chemical_melting_point ? _chemical_compound_source ? # for minerals and # natural products loop_ _atom_type_symbol _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source n 12.21260 0.00570 3.13220 9.89330 2.01250 28.99750 1.16630 0.58260 -11.52900 0.00100 0.00200 International_Tables_for_Crystallography_Vol.C(1991)_Tables_6.1.1.4_and_6.1.1.5 c 2.31000 20.84390 1.02000 10.20750 1.58860 0.56870 0.86500 51.65120 0.21560 0.00000 0.00100 International_Tables_for_Crystallography_Vol.C(1991)_Tables_6.1.1.4_and_6.1.1.5 h 0.49300 10.51090 0.32291 26.12570 0.14019 3.14236 0.04081 57.79970 0.00304 0.00000 0.00000 International_Tables_for_Crystallography_Vol.C(1991)_Tables_6.1.1.4_and_6.1.1.5 br 17.17890 2.17230 5.23580 16.57960 5.63770 0.26090 3.98510 41.43280 2.95570 0.09000 1.64300 International_Tables_for_Crystallography_Vol.C(1991)_Tables_6.1.1.4_and_6.1.1.5 #============================================================================= # 6. POWDER SPECIMEN AND CRYSTAL DATA _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz #<--must include 'x,y,z' x,y,z -x+1/2,y,z+1/2 x+1/2,-y,z -x,-y,z+1/2 _cell_length_a 12.1290(4) _cell_length_b 12.7912(4) _cell_length_c 11.0668(4) _cell_angle_alpha 90.00000 _cell_angle_beta 90.00000 _cell_angle_gamma 90.00000 _cell_volume 1716.95(10) _cell_formula_units_Z 8 _cell_measurement_temperature 478 _cell_special_details ; ? ; # The next three fields give the specimen dimensions in mm. The equatorial # plane contains the incident and diffracted beam. _pd_spec_size_axial ? # perpendicular to # equatorial plane _pd_spec_size_equat ? # parallel to # scattering vector # in transmission _pd_spec_size_thick ? # parallel to # scattering vector # in reflection # The next five fields are character fields that describe the specimen. _pd_spec_mounting '0.3 mm glass capillary' _pd_spec_mount_mode transmission _pd_spec_shape cylinder _pd_char_particle_morphology ? _pd_char_colour white # The following three fields describe the preparation of the specimen. # The cooling rate is in K/min. The pressure at which the sample was # prepared is in kPa. The temperature of preparation is in K. _pd_prep_cool_rate ? _pd_prep_pressure ? _pd_prep_temperature ? # The next four fields are normally only needed for transmission experiments. _exptl_absorpt_coefficient_mu ? _exptl_absorpt_correction_type cylinder _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #============================================================================= # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; # The following item is used to identify the equipment used to record # the powder pattern when the diffractogram was measured at a laboratory # other than the authors' home institution, e.g. when neutron or synchrotron # radiation is used. _pd_instr_location 'beamline B2 HASYLAB DESY' _pd_calibration_special_details 'NIST silicon standard (640b)' _diffrn_ambient_temperature 478 _diffrn_source ? _diffrn_radiation_type synchrotron _diffrn_source_target ? # Put here the chemical symbol of the anode _diffrn_radiation_monochromator 'Si(111) double crystal' _diffrn_measurement_device_type 'goniometer Huber' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? # Not in version 2.0.1 _diffrn_detector 'PSD detector system OBI' _diffrn_detector_type 'IP technology = OBI' _pd_meas_scan_method step _pd_meas_special_details ; ? ; # The following four items give details of the measured (not processed) # powder pattern. Angles are in degrees. _pd_meas_number_of_points 6244 _pd_meas_2theta_range_min 5.02400 _pd_meas_2theta_range_max 29.99600 _pd_meas_2theta_range_inc 0.004001 #============================================================================= # 8. REFINEMENT DATA _refine_special_details ; ? ; # Use the next field to give any special details about the fitting of the # powder pattern. _pd_proc_ls_special_details ; ? ; # The next three items are given as text. _pd_proc_ls_profile_function ? _pd_proc_ls_background_function ? _pd_proc_ls_pref_orient_corr ; ? ; # The following profile R-factors are NOT CORRECTED for background # The sum is extended to all non-excluded points. # These are the current CIF standard _pd_proc_ls_prof_R_factor 1.0963 _pd_proc_ls_prof_wR_factor 1.4437 _pd_proc_ls_prof_wR_expected 0.8012 # The following profile R-factors are CORRECTED for background # The sum is extended to all non-excluded points. # These items are not in the current CIF standard, but are defined above _pd_proc_ls_prof_cR_factor 16.7091 _pd_proc_ls_prof_cwR_factor 12.5845 _pd_proc_ls_prof_cwR_expected 6.9842 # The following items are not in the CIF standard, but are defined above _pd_proc_ls_prof_chi2 3.2467 _pd_proc_ls_prof_echi2 3.2467 # Items related to LS refinement _refine_ls_R_I_factor 5.9364 _refine_ls_number_reflns 932 _refine_ls_number_parameters 28 _refine_ls_number_restraints 134 # The following four items apply to angular dispersive measurements. # 2theta minimum, maximum and increment (in degrees) are for the # intensities used in the refinement. _pd_proc_2theta_range_min 5.0261 _pd_proc_2theta_range_max 29.9981 _pd_proc_2theta_range_inc 0.004001 _pd_proc_wavelength 0.538501 _pd_block_diffractogram_id ? # The id used for the block containing # the powder pattern profile (section 11) # Give appropriate details in the next two text fields. _pd_proc_info_excluded_regions ? _pd_proc_info_data_reduction ? # The following items are used to identify the programs used. _computing_data_collection ? _computing_structure_solution FOX _computing_structure_refinement FULLPROF _computing_molecular_graphics ? _computing_publication_material ? #============================================================================= # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type # Not in version 2.0.1 _atom_site_type_symbol N2 0.524632(17) 0.005112(17) 0.207512(17) 0.01703(10) 1.00000 Uiso N C6 0.50773(2) -0.00196(2) 0.07553(2) 0.05832(8) 1.00000 Uiso C H6a 0.51607 -0.07604 0.04639 0.07599 1.00000 Uiso H H6b 0.42798 0.01305 0.05158 0.07599 1.00000 Uiso H C5 0.580310(18) 0.066390(18) 0.000860(18) 0.05832(8) 1.00000 Uiso C H5a 0.54139 0.11730 -0.04650 0.07599 1.00000 Uiso H H5b 0.63274 0.02859 -0.04870 0.07599 1.00000 Uiso H C4 0.500332(18) 0.111343(18) 0.243283(18) 0.05832(8) 1.00000 Uiso C H4a 0.51033 0.11696 0.33167 0.07599 1.00000 Uiso H H4b 0.42432 0.12949 0.22592 0.07599 1.00000 Uiso H C3 0.578980(17) 0.187460(17) 0.175700(17) 0.05832(8) 1.00000 Uiso C H3a 0.53287 0.23607 0.12857 0.07599 1.00000 Uiso H H3b 0.62200 0.22682 0.23318 0.07599 1.00000 Uiso H C2 0.637354(16) -0.025256(16) 0.226354(16) 0.05832(8) 1.00000 Uiso C H2a 0.65315 -0.02028 0.31172 0.07599 1.00000 Uiso H H2b 0.65407 -0.09343 0.19994 0.07599 1.00000 Uiso H C1 0.721269(15) 0.057179(15) 0.166999(15) 0.05832(8) 1.00000 Uiso C H1a 0.76250 0.08822 0.21883 0.07599 1.00000 Uiso H H1b 0.76345 0.01379 0.11006 0.07599 1.00000 Uiso H N1 0.652586(14) 0.128246(14) 0.090126(14) 0.01703(10) 1.00000 Uiso N H1n 0.69850 0.17360 0.05116 0.07599 1.00000 Uiso H Br1 0.734465(9) 0.304465(9) -0.098515(9) 0.025386(4) 1.00000 Uiso Br N12 0.535495(15) 0.517435(15) 0.172135(15) 0.03247(10) 1.00000 Uiso N C16 0.49804(2) 0.49418(2) 0.29321(2) 0.04132(8) 1.00000 Uiso C H16a 0.42247 0.48805 0.30776 0.07599 1.00000 Uiso H H16b 0.53670 0.43204 0.32512 0.07599 1.00000 Uiso H C15 0.542160(16) 0.586340(16) 0.373930(16) 0.04132(8) 1.00000 Uiso C H15a 0.48177 0.61901 0.41836 0.07599 1.00000 Uiso H H15b 0.59411 0.56122 0.43269 0.07599 1.00000 Uiso H C12 0.648228(14) 0.519828(14) 0.158028(14) 0.04132(8) 1.00000 Uiso C H12a 0.68065 0.45702 0.18886 0.07599 1.00000 Uiso H H12b 0.66956 0.52515 0.07084 0.07599 1.00000 Uiso H C11 0.693725(15) 0.619445(15) 0.232505(15) 0.04132(8) 1.00000 Uiso C H11a 0.72290 0.66693 0.17185 0.07599 1.00000 Uiso H H11b 0.74714 0.59613 0.28417 0.07599 1.00000 Uiso H C14 0.478907(18) 0.609217(18) 0.122367(18) 0.04132(8) 1.00000 Uiso C H14a 0.40451 0.60791 0.11868 0.07599 1.00000 Uiso H H14b 0.51057 0.62504 0.04528 0.07599 1.00000 Uiso H C13 0.520342(16) 0.706842(16) 0.210702(16) 0.04132(8) 1.00000 Uiso C H13a 0.45347 0.73175 0.24979 0.07599 1.00000 Uiso H H13b 0.55012 0.75800 0.16118 0.07599 1.00000 Uiso H N11 0.597892(13) 0.667612(13) 0.297422(13) 0.03247(10) 1.00000 Uiso N H11n 0.62505 0.72217 0.34215 0.07599 1.00000 Uiso H Br11 0.745774(9) 0.814854(9) 0.467914(9) 0.025386(4) 1.00000 Uiso Br # Note: if the displacement parameters were refined anisotropically # the U matrices should be given as for single-crystal studies. #============================================================================= #============================================================================= # Additional structures (last six sections and associated data_? identifiers) # may be added at this point. #============================================================================= # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set. # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # Attachment 'dabcoHBrII.cif' data_dabcoHBrII _database_code_depnum_ccdc_archive 'CCDC 860849' #TrackingRef 'dabcoHBrII.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4-diazabicyclo[2.2.2]octane hydrobromide ; _chemical_name_common ; dabcoHBr ; _chemical_melting_point ? _chemical_formula_moiety 'C6 H13 N2, Br' _chemical_formula_sum 'C6 H13 Br N2' _chemical_formula_weight 193.09 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' _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)' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'C m c 21' _symmetry_space_group_name_Hall ' C 2c -2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, z+1/2' '-x, y, z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' _cell_length_a 7.542(4) _cell_length_b 10.176(5) _cell_length_c 10.161(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 779.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_pressure 400000 _cell_measurement_reflns_used 2424 _cell_measurement_theta_min 3.36 _cell_measurement_theta_max 28.74 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 5.189 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.43 _exptl_absorpt_correction_T_max 0.62 _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 0.40(5) GPa (400000 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 2424 _diffrn_reflns_av_R_equivalents 0.0761 _diffrn_reflns_av_sigmaI/netI 0.0653 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 28.74 _diffrn_measured_fraction_theta_max 0.557 _diffrn_reflns_theta_full 28.74 _diffrn_measured_fraction_theta_full 0.557 _reflns_number_total 611 _reflns_number_gt 515 _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. ; _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^)+(0.0320P)^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 0.00(4) _refine_ls_number_reflns 611 _refine_ls_number_parameters 49 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0598 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.0720 _refine_ls_wR_factor_gt 0.0637 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.469 _refine_diff_density_min -0.519 _refine_diff_density_rms 0.088 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 Br1 Br 0.0000 0.05849(7) 0.15176(19) 0.0397(3) Uani 1 2 d S . . N1 N 0.5000 0.2671(6) 0.0350(6) 0.0307(19) Uani 1 2 d S . . H1N H 0.5000 0.3438 0.0810 0.037 Uiso 1 2 calc SR . . C1 C 0.5000 0.1557(7) 0.1286(12) 0.036(3) Uani 1 2 d S . . H1B H 0.3956 0.1594 0.1842 0.043 Uiso 0.50 1 calc PR . . H1C H 0.6044 0.1594 0.1842 0.043 Uiso 0.50 1 calc PR . . C2 C 0.5000 0.0279(9) 0.0474(10) 0.045(3) Uani 1 2 d S . . H2B H 0.6040 -0.0235 0.0697 0.054 Uiso 0.50 1 calc PR . . H2C H 0.3960 -0.0235 0.0697 0.054 Uiso 0.50 1 calc PR . . N2 N 0.5000 0.0545(6) -0.0915(7) 0.040(2) Uani 1 2 d S . . C3 C 0.3376(8) 0.2610(6) -0.0479(6) 0.0358(17) Uani 1 1 d . . . H3A H 0.3345 0.3352 -0.1078 0.043 Uiso 1 1 calc R . . H3B H 0.2328 0.2643 0.0073 0.043 Uiso 1 1 calc R . . C4 C 0.3410(11) 0.1335(6) -0.1251(7) 0.048(2) Uani 1 1 d . . . H4A H 0.2350 0.0831 -0.1055 0.057 Uiso 1 1 calc R . . H4B H 0.3413 0.1528 -0.2185 0.057 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 Br1 0.0379(6) 0.0368(5) 0.0443(5) -0.0072(8) 0.000 0.000 N1 0.036(7) 0.024(4) 0.032(5) -0.014(3) 0.000 0.000 C1 0.056(7) 0.035(5) 0.016(7) 0.011(5) 0.000 0.000 C2 0.052(9) 0.038(7) 0.044(7) 0.008(5) 0.000 0.000 N2 0.051(7) 0.022(5) 0.046(5) -0.014(4) 0.000 0.000 C3 0.030(6) 0.033(5) 0.045(5) 0.000(3) -0.002(3) 0.005(3) C4 0.058(7) 0.039(5) 0.045(5) -0.003(4) -0.008(3) -0.004(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 C1 1.480(11) . ? N1 C3 1.488(6) . ? N1 C3 1.488(6) 4_655 ? N1 H1N 0.9100 . ? C1 C2 1.540(12) . ? C1 H1B 0.9700 . ? C1 H1C 0.9700 . ? C2 N2 1.437(12) . ? C2 H2B 0.9700 . ? C2 H2C 0.9700 . ? N2 C4 1.484(8) 4_655 ? N2 C4 1.484(8) . ? C3 C4 1.516(9) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 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 C1 N1 C3 109.4(4) . . ? C1 N1 C3 109.4(4) . 4_655 ? C3 N1 C3 110.8(6) . 4_655 ? C1 N1 H1N 109.1 . . ? C3 N1 H1N 109.1 . . ? C3 N1 H1N 109.1 4_655 . ? N1 C1 C2 107.6(8) . . ? N1 C1 H1B 110.2 . . ? C2 C1 H1B 110.2 . . ? N1 C1 H1C 110.2 . . ? C2 C1 H1C 110.2 . . ? H1B C1 H1C 108.5 . . ? N2 C2 C1 111.6(7) . . ? N2 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? N2 C2 H2C 109.3 . . ? C1 C2 H2C 109.3 . . ? H2B C2 H2C 108.0 . . ? C2 N2 C4 109.1(5) . 4_655 ? C2 N2 C4 109.1(5) . . ? C4 N2 C4 107.9(8) 4_655 . ? N1 C3 C4 108.4(5) . . ? N1 C3 H3A 110.0 . . ? C4 C3 H3A 110.0 . . ? N1 C3 H3B 110.0 . . ? C4 C3 H3B 110.0 . . ? H3A C3 H3B 108.4 . . ? N2 C4 C3 111.0(6) . . ? N2 C4 H4A 109.4 . . ? C3 C4 H4A 109.4 . . ? N2 C4 H4B 109.4 . . ? C3 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ?