Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'David, William' 'Florence, Alastair' 'Frampton, Christopher S.' 'Kennedy, Alan R.' 'Shankland, Kenneth' 'Shankland, Norman' _publ_contact_author_name 'Dr Norman Shankland' _publ_contact_author_address ; University of Strathlcyde Glasgow G43 ONR UNITED KINGDOM ; _publ_contact_author_email n.shankland@strath.ac.uk _publ_contact_author_fax 0141-552-6443 _publ_contact_author_phone 0141-548-2969 _publ_contact_letter ; This cif contains details of the crystal structure of zopiclone (form II) determined from synchrotron powder diffraction data as discussed in the the attached manuscript, "Structural transformations in zopiclone". Please deposit the crystal structure with the Cambridge Crystallographic Data Centre. ; _publ_section_references ; Molecular Structure Corporation (1985, 1992). teXsan. Crystal Structure Analysis Package, The Woodlands, TX, USA 77381 ; _publ_requested_journal 'Chemical Communications' _publ_section_title 'Structural Transformations in Zopiclone' #============================================================================= data_zopanh-powder _database_code_CSD 171566 #============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; (6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-oxo-5H-pyrrolo(3,4-b)pyrazin-5-yl)-4- methyl-1-piperazine carboxylate ; _chemical_name_common zopiclone _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C17 Cl N6 O3' _chemical_formula_weight ? _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source 'O' 'O' 'International Tables Vol C Table 6.1.1.4' 'N' 'N' 'International Tables Vol C Table 6.1.1.4' 'Cl' 'Cl' 'International Tables Vol C Table 6.1.1.4' 'C' 'C' 'International Tables Vol C Table 6.1.1.4' #============================================================================== # 6. POWDER SPECIMEN AND CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,1/2+y,1/2-z' '-x,-y,-z' 'x,1/2-y,1/2+z' _cell_length_a 15.2023(4) _cell_length_b 7.1510(1) _cell_length_c 17.6577(3) _cell_angle_alpha 90.0 _cell_angle_beta 111.213(1) _cell_angle_gamma 90.0 _cell_volume 1789.5 _cell_formula_units_Z 4 _cell_measurement_temperature 325 _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 10 # perpendicular to # equatorial plane _pd_spec_size_equat 1 # 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 '1.0mm borosilicate 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 325 # The next four fields are normally only needed for transmission experiments. _exptl_absorpt_coefficient_mu ? _exptl_absorpt_correction_type ? # include if applicable _exptl_absorpt_process_details ? # include if applicable _exptl_absorpt_correction_T_min ? # include if applicable _exptl_absorpt_correction_T_max ? # include if applicable #============================================================================== # 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 'BM16 diffractometer, ESRF, Grenoble, France' _pd_calibration_special_details 'Rietveld refinement against Si powder pattern' _diffrn_ambient_temperature 325 _diffrn_source synchrotron _diffrn_source_target ? _diffrn_source_type 'ESRF BM16' _diffrn_measurement_device_type '2 circle diffractometer' _diffrn_detector 'multiple crystal analyser' _diffrn_detector_type ? # make or model of detector _pd_meas_scan_method step # options are 'step', 'cont', # 'tof', 'fixed' or # 'disp' (= dispersive) _pd_meas_special_details ; Total data collection time was about 200 minutes for the data range specified. ; # The following six items are used for angular dispersive measurements only. _diffrn_radiation_wavelength 0.80008 _diffrn_radiation_monochromator 'Si 111' # The following four items give details of the measured (not processed) # powder pattern. Angles are in degrees. _pd_meas_number_of_points 3401 _pd_meas_2theta_range_min 1.000 _pd_meas_2theta_range_max 18.000 _pd_meas_2theta_range_inc 0.005 # The following three items are used for time-of-flight measurements only. _pd_instr_dist_src/spec ? _pd_instr_dist_spec/detc ? _pd_meas_2theta_fixed ? #============================================================================== # 8. REFINEMENT DATA # Use the next field to give any special details about the fitting of the # powder pattern. _pd_proc_ls_special_details ; The structure solution was obtained by global optimisation using the DASH V1.0 program. The internal coordinate description of the zopiclone molecule was derived from the known single crystal structure of monoclinic zopiclone dihydrate. Background subtracted data were used in the structure solution. Given the very limited resolution of the diffraction data utilised (2.55 Angstroms, 109 reflections), only a ‘rigid-body’ refinement is appropriate. Accordingly, Rietveld refinement of the output DASH structural model was limited to varying only the scale factor and ten term polynomial background against the measured, non-background subtracted diffraction data. As no atomic coordinates were refined, there are no estimated standard deviations for the coordinates. ; # The next three items are given as text. _pd_proc_ls_profile_function 'Voigt with axial divergence correction' _pd_proc_ls_background_function 'Chebyshev polynomial' _pd_proc_ls_pref_orient_corr ? _pd_proc_ls_prof_R_factor 11.29 _pd_proc_ls_prof_wR_factor 14.67 _pd_proc_ls_prof_wR_expected 1.67 _refine_ls_R_I_factor ? _refine_ls_R_Fsqd_factor ? _refine_ls_R_factor_all ? _refine_special_details ; ? ; _refine_ls_matrix_type fullcycle _refine_ls_weighting_scheme sigma _refine_ls_weighting_details ? _refine_ls_hydrogen_treatment undef _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_parameters 11 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_special_details ; ? ; # The following item is the same as CHI, the square root of 'CHI squared' _refine_ls_goodness_of_fit_all 8.77 _refine_ls_restrained_S_all ? _refine_ls_restrained_S_obs ? _refine_ls_shift/su_max ? _refine_ls_shift/su_mean ? # 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 1.000 _pd_proc_2theta_range_max 18.000 _pd_proc_2theta_range_inc 0.005 _pd_proc_wavelength 0.8008 # 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 'BM16 instrument software' _computing_cell_refinement 'DASH V1.0' _computing_data_reduction 'BM16 instrument software' _computing_structure_solution 'DASH V1.0' _computing_structure_refinement 'DASH V1.0' _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_occupancy _atom_site_adp_type _atom_site_B_iso_or_equiv N1 0.50259 0.71429 0.26132 1.0 Biso 3.0 C2 0.21104 0.54561 0.44475 1.0 Biso 3.0 O3 0.33328 0.84964 0.30740 1.0 Biso 3.0 O4 0.21603 0.66512 0.22532 1.0 Biso 3.0 N5 0.27880 0.58824 0.41630 1.0 Biso 3.0 N6 0.42437 0.70612 0.43097 1.0 Biso 3.0 C7 0.66144 0.80291 0.34321 1.0 Biso 3.0 C8 0.55722 0.77126 0.40410 1.0 Biso 3.0 C9 0.23917 0.80397 0.26735 1.0 Biso 3.0 C10 0.39536 0.69713 0.34198 1.0 Biso 3.0 C11 0.48771 0.72851 0.33098 1.0 Biso 3.0 C12 0.03162 0.91013 0.29574 1.0 Biso 3.0 C13 0.22024 0.58037 0.52423 1.0 Biso 3.0 N14 0.05895 1.06261 0.35585 1.0 Biso 3.0 C15 0.30109 0.66627 0.57634 1.0 Biso 3.0 C16 0.08043 0.93152 0.23438 1.0 Biso 3.0 C17 0.37175 0.71192 0.54776 1.0 Biso 3.0 Cl18 0.13198 0.51019 0.55819 1.0 Biso 3.0 C19 0.59209 0.75160 0.26952 1.0 Biso 3.0 C20 0.35696 0.66838 0.46703 1.0 Biso 3.0 O21 0.55785 0.78337 0.54260 1.0 Biso 3.0 C22 0.51757 0.75912 0.47024 1.0 Biso 3.0 N23 0.18298 0.93849 0.27738 1.0 Biso 3.0 C24 0.16175 1.06258 0.39822 1.0 Biso 3.0 N25 0.64602 0.81269 0.41332 1.0 Biso 3.0 C26 0.21236 1.08706 0.33874 1.0 Biso 3.0 C27 0.01299 1.03760 0.41550 1.0 Biso 3.0 #============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl18 C13 1.7303 . . yes O3 C9 1.3862 . . yes O3 C10 1.4268 . . yes O4 C9 1.2131 . . yes O21 C22 1.2130 . . yes N1 C11 1.3326 . . yes N1 C19 1.3420 . . yes N5 C2 1.3345 . . yes N5 C20 1.3313 . . yes N6 C10 1.4718 . . yes N6 C20 1.4144 . . yes N6 C22 1.3860 . . yes N14 C12 1.4728 . . yes N14 C24 1.4683 . . yes N14 C27 1.4704 . . yes N23 C9 1.3401 . . yes N23 C16 1.4673 . . yes N23 C26 1.4670 . . yes N25 C7 1.3426 . . yes N25 C8 1.3333 . . yes C2 C13 1.3816 . . no C7 C19 1.3952 . . no C8 C11 1.3747 . . no C8 C22 1.4981 . . no C10 C11 1.5021 . . no C12 C16 1.5263 . . no C13 C15 1.3843 . . no C15 C17 1.3811 . . no C17 C20 1.3956 . . no C24 C26 1.5200 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O3 C10 116.04 . . . yes C11 N1 C19 112.91 . . . yes C2 N5 C20 117.88 . . . yes C10 N6 C20 119.09 . . . yes C10 N6 C22 113.78 . . . yes C20 N6 C22 127.08 . . . yes C12 N14 C24 109.74 . . . yes C12 N14 C27 110.06 . . . yes C24 N14 C27 109.21 . . . yes C9 N23 C16 121.06 . . . yes C9 N23 C26 125.39 . . . yes C16 N23 C26 112.91 . . . yes C7 N25 C8 112.50 . . . yes N5 C2 C13 122.21 . . . yes N25 C7 C19 123.27 . . . yes N25 C8 C11 124.36 . . . yes N25 C8 C22 126.36 . . . yes C11 C8 C22 109.26 . . . no O3 C9 O4 121.48 . . . yes O3 C9 N23 110.67 . . . yes O4 C9 N23 127.65 . . . yes O3 C10 N6 108.65 . . . yes O3 C10 C11 109.57 . . . yes N6 C10 C11 101.45 . . . yes N1 C11 C8 123.67 . . . yes N1 C11 C10 125.92 . . . yes C8 C11 C10 110.40 . . . no N14 C12 C16 110.77 . . . yes Cl18 C13 C2 119.58 . . . yes Cl18 C13 C15 120.78 . . . yes C2 C13 C15 119.62 . . . no C13 C15 C17 118.88 . . . no N23 C16 C12 109.54 . . . yes C15 C17 C20 117.48 . . . no N1 C19 C7 123.19 . . . yes N5 C20 N6 113.26 . . . yes N5 C20 C17 123.92 . . . yes N6 C20 C17 122.82 . . . yes O21 C22 N6 126.95 . . . yes O21 C22 C8 128.37 . . . yes N6 C22 C8 104.64 . . . yes N14 C24 C26 111.07 . . . yes N23 C26 C24 109.39 . . . yes 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 C9 O3 C10 N6 -108.48 . . . . no C9 O3 C10 C11 141.50 . . . . no C10 O3 C9 O4 -39.34 . . . . no C10 O3 C9 N23 145.36 . . . . no C11 N1 C19 C7 -1.03 . . . . no C19 N1 C11 C8 -1.88 . . . . no C19 N1 C11 C10 179.51 . . . . no C2 N5 C20 N6 179.49 . . . . no C2 N5 C20 C17 -0.64 . . . . no C20 N5 C2 C13 -0.61 . . . . no C10 N6 C20 N5 14.04 . . . . no C10 N6 C20 C17 -165.84 . . . . no C22 N6 C20 N5 -168.48 . . . . no C20 N6 C10 O3 69.37 . . . . no C20 N6 C10 C11 -175.23 . . . . no C22 N6 C10 O3 -108.44 . . . . no C22 N6 C10 C11 6.96 . . . . no C20 N6 C22 C8 177.38 . . . . no C20 N6 C22 O21 -0.34 . . . . no C22 N6 C20 C17 11.65 . . . . no C10 N6 C22 O21 177.26 . . . . no C10 N6 C22 C8 -5.02 . . . . no C27 N14 C12 C16 -178.75 . . . . no C12 N14 C24 C26 58.97 . . . . no C27 N14 C24 C26 179.69 . . . . no C24 N14 C12 C16 -58.55 . . . . no C9 N23 C16 C12 115.39 . . . . no C26 N23 C16 C12 -55.98 . . . . no C9 N23 C26 C24 -114.80 . . . . no C16 N23 C9 O3 174.03 . . . . no C16 N23 C9 O4 -0.90 . . . . no C26 N23 C9 O3 -15.73 . . . . no C26 N23 C9 O4 169.33 . . . . no C16 N23 C26 C24 56.12 . . . . no C7 N25 C8 C22 176.64 . . . . no C8 N25 C7 C19 -1.09 . . . . no C7 N25 C8 C11 -1.84 . . . . no N5 C2 C13 C15 1.58 . . . . no N5 C2 C13 Cl18 -176.65 . . . . no N25 C7 C19 N1 2.67 . . . . no N25 C8 C11 N1 3.58 . . . . no N25 C8 C22 N6 -177.97 . . . . no C11 C8 C22 O21 178.37 . . . . no C11 C8 C22 N6 0.69 . . . . no N25 C8 C11 C10 -177.61 . . . . no C22 C8 C11 N1 -175.12 . . . . no C22 C8 C11 C10 3.69 . . . . no N25 C8 C22 O21 -0.30 . . . . no O3 C10 C11 N1 -72.75 . . . . no O3 C10 C11 C8 108.47 . . . . no N6 C10 C11 N1 172.52 . . . . no N6 C10 C11 C8 -6.25 . . . . no N14 C12 C16 N23 56.49 . . . . no Cl18 C13 C15 C17 176.92 . . . . no C2 C13 C15 C17 -1.29 . . . . no C13 C15 C17 C20 0.13 . . . . no C15 C17 C20 N5 0.87 . . . . no C15 C17 C20 N6 -179.27 . . . . no N14 C24 C26 N23 -57.03 . . . . no #============================================================================== #============================================================================= data_zopdih-powder _database_code_CSD 171567 #============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; (6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-oxo-5H-pyrrolo(3,4-b)pyrazin-5-yl)-4- methyl-1-piperazine carboxylate ; _chemical_name_common 'zopiclone dihydrate' _chemical_formula_moiety 'C17 Cl N6 O3, 2(O)' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C17 Cl N6 O5' _chemical_formula_weight 403.68 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source 'O' 'O' 'International Tables Vol C Table 6.1.1.4' 'N' 'N' 'International Tables Vol C Table 6.1.1.4' 'Cl' 'Cl' 'International Tables Vol C Table 6.1.1.4' 'C' 'C' 'International Tables Vol C Table 6.1.1.4' #============================================================================== # 6. POWDER SPECIMEN AND CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,1/2+y,1/2-z' '-x,-y,-z' 'x,1/2-y,1/2+z' _cell_length_a 16.4834(1) _cell_length_b 7.1465(1) _cell_length_c 17.4026(1) _cell_angle_alpha 90.0 _cell_angle_beta 109.8065(4) _cell_angle_gamma 90.0 _cell_volume 1928.7 _cell_formula_units_Z 4 _cell_measurement_temperature 298 _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 10 # perpendicular to # equatorial plane _pd_spec_size_equat 1 # 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 '1.0mm borosilicate 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 298 # The next four fields are normally only needed for transmission experiments. _exptl_absorpt_coefficient_mu ? _exptl_absorpt_correction_type ? # include if applicable _exptl_absorpt_process_details ? # include if applicable _exptl_absorpt_correction_T_min ? # include if applicable _exptl_absorpt_correction_T_max ? # include if applicable #============================================================================== # 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 'BM16 diffractometer, ESRF, Grenoble, France' _pd_calibration_special_details 'Rietveld refinement against Si powder pattern' _diffrn_ambient_temperature 298 _diffrn_source synchrotron _diffrn_source_target ? _diffrn_source_type 'ESRF BM16' _diffrn_measurement_device_type '2 circle diffractometer' _diffrn_detector 'multiple crystal analyser' _diffrn_detector_type ? # make or model of detector _pd_meas_scan_method step # options are 'step', 'cont', # 'tof', 'fixed' or # 'disp' (= dispersive) _pd_meas_special_details ; Total data collection time was about 60 minutes for the data range specified. ; # The following six items are used for angular dispersive measurements only. _diffrn_radiation_wavelength 0.80008 _diffrn_radiation_monochromator 'Si 111' # The following four items give details of the measured (not processed) # powder pattern. Angles are in degrees. _pd_meas_number_of_points 4401 _pd_meas_2theta_range_min 1.000 _pd_meas_2theta_range_max 23.000 _pd_meas_2theta_range_inc 0.005 # The following three items are used for time-of-flight measurements only. _pd_instr_dist_src/spec ? _pd_instr_dist_spec/detc ? _pd_meas_2theta_fixed ? #============================================================================== # 8. REFINEMENT DATA # Use the next field to give any special details about the fitting of the # powder pattern. _pd_proc_ls_special_details ; The structure solution was obtained by global optimisation using the DASH V1.0 program. The internal coordinate description of the zopiclone molecule was derived from the known single crystal structure of monoclinic zopiclone dihydrate. Background subtracted data were used in the structure solution. Given the very limited resolution of the diffraction data utilised (2.00 Angstroms, 254 reflections), only a ‘rigid-body’ refinement is appropriate. Accordingly, Rietveld refinement of the output DASH structural model was limited to varying only the scale factor and ten term polynomial background against the measured, non-background subtracted diffraction data. As no atomic coordinates were refined, there are no estimated standard deviations for the coordinates. ; # The next three items are given as text. _pd_proc_ls_profile_function 'Voigt with axial divergence correction' _pd_proc_ls_background_function 'Chebyshev polynomial' _pd_proc_ls_pref_orient_corr ? _pd_proc_ls_prof_R_factor 14.02 _pd_proc_ls_prof_wR_factor 17.56 _pd_proc_ls_prof_wR_expected 3.57 _refine_ls_R_I_factor ? _refine_ls_R_Fsqd_factor ? _refine_ls_R_factor_all ? _refine_special_details ? _refine_ls_matrix_type fullcycle _refine_ls_weighting_scheme sigma _refine_ls_weighting_details ? _refine_ls_hydrogen_treatment undef _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_parameters 11 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_special_details ; ? ; # The following item is the same as CHI, the square root of 'CHI squared' _refine_ls_goodness_of_fit_all 4.89 _refine_ls_restrained_S_all ? _refine_ls_restrained_S_obs ? _refine_ls_shift/su_max ? _refine_ls_shift/su_mean ? # 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 1.000 _pd_proc_2theta_range_max 23.000 _pd_proc_2theta_range_inc 0.005 _pd_proc_wavelength 0.8008 # 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 'BM16 instrument software' _computing_cell_refinement 'DASH V1.0' _computing_data_reduction 'BM16 instrument software' _computing_structure_solution 'DASH V1.0' _computing_structure_refinement 'DASH V1.0' _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_occupancy _atom_site_adp_type _atom_site_B_iso_or_equiv N1 -0.00367 0.27874 0.26396 1.0 Biso 3.0 C2 0.26362 0.45841 0.62616 1.0 Biso 3.0 O3 0.15474 0.15909 0.41387 1.0 Biso 3.0 O4 0.25783 0.35759 0.40316 1.0 Biso 3.0 N5 0.20213 0.41080 0.55646 1.0 Biso 3.0 N6 0.06894 0.29193 0.48375 1.0 Biso 3.0 C7 -0.14633 0.17369 0.25161 1.0 Biso 3.0 C8 -0.05127 0.21444 0.37641 1.0 Biso 3.0 C9 0.23968 0.21411 0.43087 1.0 Biso 3.0 C10 0.09462 0.30501 0.41074 1.0 Biso 3.0 C11 0.01078 0.26493 0.34387 1.0 Biso 3.0 C12 0.42996 0.11976 0.58750 1.0 Biso 3.0 C13 0.25409 0.43359 0.70137 1.0 Biso 3.0 N14 0.40793 -0.04138 0.62939 1.0 Biso 3.0 C15 0.17946 0.35274 0.70575 1.0 Biso 3.0 C16 0.38744 0.10204 0.49508 1.0 Biso 3.0 C17 0.11532 0.30205 0.63420 1.0 Biso 3.0 Cl18 0.33430 0.50983 0.78874 1.0 Biso 3.0 C19 -0.08462 0.23272 0.21836 1.0 Biso 3.0 C20 0.13000 0.33559 0.56100 1.0 Biso 3.0 O21 -0.05056 0.20024 0.51693 1.0 Biso 3.0 C22 -0.01480 0.22941 0.46759 1.0 Biso 3.0 N23 0.29384 0.08271 0.47450 1.0 Biso 3.0 C24 0.31395 -0.05365 0.60810 1.0 Biso 3.0 N25 -0.13149 0.16436 0.33229 1.0 Biso 3.0 C26 0.26984 -0.07481 0.51642 1.0 Biso 3.0 C27 0.44781 -0.02005 0.71835 1.0 Biso 3.0 O28 0.45617 0.61386 0.58097 1.0 Biso 3.0 O29 0.39666 0.92077 0.91278 1.0 Biso 3.0 #============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl18 C13 1.7304 . . yes O3 C9 1.3863 . . yes O3 C10 1.4268 . . yes O4 C9 1.2129 . . yes O21 C22 1.2129 . . yes N1 C11 1.3326 . . yes N1 C19 1.3419 . . yes N5 C2 1.3346 . . yes N5 C20 1.3313 . . yes N6 C10 1.4720 . . yes N6 C20 1.4145 . . yes N6 C22 1.3860 . . yes N14 C12 1.4727 . . yes N14 C24 1.4682 . . yes N14 C27 1.4705 . . yes N23 C9 1.3401 . . yes N23 C16 1.4674 . . yes N23 C26 1.4668 . . yes N25 C7 1.3427 . . yes N25 C8 1.3334 . . yes C2 C13 1.3815 . . no C7 C19 1.3951 . . no C8 C11 1.3746 . . no C8 C22 1.4981 . . no C10 C11 1.5021 . . no C12 C16 1.5265 . . no C13 C15 1.3844 . . no C15 C17 1.3810 . . no C17 C20 1.3956 . . no C24 C26 1.5202 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O3 C10 116.04 . . . yes C11 N1 C19 112.91 . . . yes C2 N5 C20 117.87 . . . yes C10 N6 C20 119.09 . . . yes C10 N6 C22 113.78 . . . yes C20 N6 C22 127.08 . . . yes C12 N14 C24 109.74 . . . yes C12 N14 C27 110.05 . . . yes C24 N14 C27 109.20 . . . yes C9 N23 C16 121.05 . . . yes C9 N23 C26 125.41 . . . yes C16 N23 C26 112.91 . . . yes C7 N25 C8 112.49 . . . yes N5 C2 C13 122.22 . . . yes N25 C7 C19 123.27 . . . yes N25 C8 C11 124.36 . . . yes N25 C8 C22 126.36 . . . yes C11 C8 C22 109.27 . . . no O3 C9 O4 121.48 . . . yes O3 C9 N23 110.67 . . . yes O4 C9 N23 127.66 . . . yes O3 C10 N6 108.65 . . . yes O3 C10 C11 109.57 . . . yes N6 C10 C11 101.45 . . . yes N1 C11 C8 123.68 . . . yes N1 C11 C10 125.91 . . . yes C8 C11 C10 110.40 . . . no N14 C12 C16 110.76 . . . yes Cl18 C13 C2 119.59 . . . yes Cl18 C13 C15 120.77 . . . yes C2 C13 C15 119.62 . . . no C13 C15 C17 118.88 . . . no N23 C16 C12 109.53 . . . yes C15 C17 C20 117.48 . . . no N1 C19 C7 123.19 . . . yes N5 C20 N6 113.26 . . . yes N5 C20 C17 123.92 . . . yes N6 C20 C17 122.82 . . . yes O21 C22 N6 126.96 . . . yes O21 C22 C8 128.37 . . . yes N6 C22 C8 104.63 . . . yes N14 C24 C26 111.06 . . . yes N23 C26 C24 109.39 . . . yes 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 C9 O3 C10 N6 -107.67 . . . . no C9 O3 C10 C11 142.31 . . . . no C10 O3 C9 O4 -38.38 . . . . no C10 O3 C9 N23 146.32 . . . . no C11 N1 C19 C7 -1.03 . . . . no C19 N1 C11 C8 -1.87 . . . . no C19 N1 C11 C10 179.50 . . . . no C2 N5 C20 N6 179.48 . . . . no C2 N5 C20 C17 -0.65 . . . . no C20 N5 C2 C13 -0.59 . . . . no C10 N6 C20 N5 9.13 . . . . no C10 N6 C20 C17 -170.74 . . . . no C22 N6 C20 N5 -173.39 . . . . no C20 N6 C10 O3 69.36 . . . . no C20 N6 C10 C11 -175.24 . . . . no C22 N6 C10 O3 -108.44 . . . . no C22 N6 C10 C11 6.97 . . . . no C20 N6 C22 C8 177.39 . . . . no C20 N6 C22 O21 -0.33 . . . . no C22 N6 C20 C17 6.73 . . . . no C10 N6 C22 O21 177.26 . . . . no C10 N6 C22 C8 -5.03 . . . . no C27 N14 C12 C16 -178.76 . . . . no C12 N14 C24 C26 58.98 . . . . no C27 N14 C24 C26 179.69 . . . . no C24 N14 C12 C16 -58.56 . . . . no C9 N23 C16 C12 115.39 . . . . no C26 N23 C16 C12 -55.98 . . . . no C9 N23 C26 C24 -114.80 . . . . no C16 N23 C9 O3 175.50 . . . . no C16 N23 C9 O4 0.56 . . . . no C26 N23 C9 O3 -14.25 . . . . no C26 N23 C9 O4 170.81 . . . . no C16 N23 C26 C24 56.13 . . . . no C7 N25 C8 C22 176.64 . . . . no C8 N25 C7 C19 -1.09 . . . . no C7 N25 C8 C11 -1.83 . . . . no N5 C2 C13 C15 1.56 . . . . no N5 C2 C13 Cl18 -176.66 . . . . no N25 C7 C19 N1 2.66 . . . . no N25 C8 C11 N1 3.57 . . . . no N25 C8 C22 N6 -177.96 . . . . no C11 C8 C22 O21 178.36 . . . . no C11 C8 C22 N6 0.69 . . . . no N25 C8 C11 C10 -177.61 . . . . no C22 C8 C11 N1 -175.12 . . . . no C22 C8 C11 C10 3.70 . . . . no N25 C8 C22 O21 -0.30 . . . . no O3 C10 C11 N1 -72.75 . . . . no O3 C10 C11 C8 108.47 . . . . no N6 C10 C11 N1 172.52 . . . . no N6 C10 C11 C8 -6.26 . . . . no N14 C12 C16 N23 56.49 . . . . no Cl18 C13 C15 C17 176.92 . . . . no C2 C13 C15 C17 -1.28 . . . . no C13 C15 C17 C20 0.13 . . . . no C15 C17 C20 N5 0.88 . . . . no C15 C17 C20 N6 -179.26 . . . . no N14 C24 C26 N23 -57.04 . . . . no #============================================================================== #============================================================================= data_zoport-powder _database_code_CSD 171568 #============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; (6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-oxo-5H-pyrrolo(3,4-b)pyrazin-5-yl)-4- methyl-1-piperazine carboxylate ; _chemical_name_common 'zopiclone' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C17 Cl N6 O3' _chemical_formula_weight ? _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source 'O' 'O' 'International Tables Vol C Table 6.1.1.4' 'N' 'N' 'International Tables Vol C Table 6.1.1.4' 'Cl' 'Cl' 'International Tables Vol C Table 6.1.1.4' 'C' 'C' 'International Tables Vol C Table 6.1.1.4' #============================================================================== # 6. POWDER SPECIMEN AND CRYSTAL DATA _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '-x+1/2, -y,z+1/2' ' -x,y+1/2,1/2-z' 'x+1/2,1/2-y, -z' _cell_length_a 5.5813(1) _cell_length_b 8.8467(1) _cell_length_c 35.6588(3) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_volume 1760.7 _cell_formula_units_Z 4 _cell_measurement_temperature 298 _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 10 # perpendicular to # equatorial plane _pd_spec_size_equat 1 # 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 '1.0mm borosilicate 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 298 # The next four fields are normally only needed for transmission experiments. _exptl_absorpt_coefficient_mu ? _exptl_absorpt_correction_type ? # include if applicable _exptl_absorpt_process_details ? # include if applicable _exptl_absorpt_correction_T_min ? # include if applicable _exptl_absorpt_correction_T_max ? # include if applicable #============================================================================== # 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 'BM16 diffractometer, ESRF, Grenoble, France' _pd_calibration_special_details 'Rietveld refinement against Si powder pattern' _diffrn_ambient_temperature 298 _diffrn_source synchrotron _diffrn_source_target ? _diffrn_source_type 'ESRF BM16' _diffrn_measurement_device_type '2 circle diffractometer' _diffrn_detector 'multiple crystal analyser' _diffrn_detector_type ? # make or model of detector _pd_meas_scan_method step # options are 'step', 'cont', # 'tof', 'fixed' or # 'disp' (= dispersive) _pd_meas_special_details ; Total data collection time was about 42 minutes for the data range specified. ; # The following six items are used for angular dispersive measurements only. _diffrn_radiation_wavelength 0.80008 _diffrn_radiation_monochromator 'Si 111' # The following four items give details of the measured (not processed) # powder pattern. Angles are in degrees. _pd_meas_number_of_points 10500 _pd_meas_2theta_range_min 1.000 _pd_meas_2theta_range_max 22.000 _pd_meas_2theta_range_inc 0.002 # The following three items are used for time-of-flight measurements only. _pd_instr_dist_src/spec ? _pd_instr_dist_spec/detc ? _pd_meas_2theta_fixed ? #============================================================================== # 8. REFINEMENT DATA # Use the next field to give any special details about the fitting of the # powder pattern. _pd_proc_ls_special_details ; The structure solution was obtained by global optimisation using the DASH V1.0 program. The internal coordinate description of the zopiclone molecule was derived from the known single crystal structure of orthorhombic zopiclone. Background subtracted data were used in the structure solution. Given the very limited resolution of the diffraction data utilised (2.10 Angstroms, 143 reflections), only a ‘rigid-body’ refinement is appropriate. Accordingly, Rietveld refinement of the output DASH structural model was limited to varying only the scale factor and ten term polynomial background against the measured, non-background subtracted diffraction data. As no atomic coordinates were refined, there are no estimated standard deviations for the coordinates. ; # The next three items are given as text. _pd_proc_ls_profile_function 'Voigt with axial divergence correction' _pd_proc_ls_background_function 'Chebyshev polynomial' _pd_proc_ls_pref_orient_corr ? _pd_proc_ls_prof_R_factor 14.41 _pd_proc_ls_prof_wR_factor 18.34 _pd_proc_ls_prof_wR_expected 7.86 _refine_ls_R_I_factor ? _refine_ls_R_Fsqd_factor ? _refine_ls_R_factor_all ? _refine_special_details ; ? ; _refine_ls_matrix_type fullcycle _refine_ls_weighting_scheme sigma _refine_ls_weighting_details ? _refine_ls_hydrogen_treatment undef _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_parameters 11 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_special_details ; ? ; # The following item is the same as CHI, the square root of 'CHI squared' _refine_ls_goodness_of_fit_all 2.34 _refine_ls_restrained_S_all ? _refine_ls_restrained_S_obs ? _refine_ls_shift/su_max ? _refine_ls_shift/su_mean ? # 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 1.000 _pd_proc_2theta_range_max 22.000 _pd_proc_2theta_range_inc 0.002 _pd_proc_wavelength 0.8008 # 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 'BM16 instrument software' _computing_cell_refinement 'DASH V1.0' _computing_data_reduction 'BM16 instrument software' _computing_structure_solution 'DASH V1.0' _computing_structure_refinement 'DASH V1.0' _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_occupancy _atom_site_adp_type _atom_site_B_iso_or_equiv Cl1 -0.29946 0.36779 0.89460 1.0 Biso 3.0 C2 -0.09932 0.48640 0.87151 1.0 Biso 3.0 C3 -0.12206 0.63701 0.87558 1.0 Biso 3.0 N4 0.03038 0.73578 0.85972 1.0 Biso 3.0 C5 0.20802 0.67938 0.83933 1.0 Biso 3.0 N6 0.36836 0.78717 0.82413 1.0 Biso 3.0 C7 0.54720 0.76597 0.79834 1.0 Biso 3.0 O8 0.60660 0.64442 0.78412 1.0 Biso 3.0 C9 0.64671 0.91725 0.79083 1.0 Biso 3.0 N10 0.82623 0.95203 0.76879 1.0 Biso 3.0 C11 0.87197 1.10037 0.76705 1.0 Biso 3.0 C12 0.75359 1.20586 0.78739 1.0 Biso 3.0 N13 0.56970 1.16858 0.81163 1.0 Biso 3.0 C14 0.52689 1.02129 0.81228 1.0 Biso 3.0 C15 0.35640 0.94283 0.83808 1.0 Biso 3.0 O16 0.44939 0.94580 0.87510 1.0 Biso 3.0 C17 0.33973 1.03228 0.90093 1.0 Biso 3.0 O18 0.15188 1.10185 0.89400 1.0 Biso 3.0 N19 0.45276 1.02936 0.93396 1.0 Biso 3.0 C20 0.69728 0.98945 0.93772 1.0 Biso 3.0 C21 0.74640 0.91666 0.97547 1.0 Biso 3.0 N22 0.66969 1.01822 1.00549 1.0 Biso 3.0 C23 0.41452 1.05000 1.00139 1.0 Biso 3.0 C24 0.36489 1.12372 0.96475 1.0 Biso 3.0 C25 0.72630 0.95374 1.04199 1.0 Biso 3.0 C26 0.23577 0.52462 0.83348 1.0 Biso 3.0 C27 0.08318 0.42810 0.84966 1.0 Biso 3.0 #============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.7398 . . yes O8 C7 1.2342 . . yes O16 C15 1.4187 . . yes O16 C17 1.3447 . . yes O18 C17 1.2406 . . yes N4 C3 1.3443 . . yes N4 C5 1.3269 . . yes N6 C5 1.4156 . . yes N6 C7 1.3701 . . yes N6 C15 1.4657 . . yes N10 C9 1.3101 . . yes N10 C11 1.3384 . . yes N13 C12 1.3818 . . yes N13 C14 1.3250 . . yes N19 C17 1.3364 . . yes N19 C20 1.4160 . . yes N19 C24 1.4638 . . yes N22 C21 1.4617 . . yes N22 C23 1.4590 . . yes N22 C25 1.4558 . . yes C2 C3 1.3463 . . no C2 C27 1.3822 . . no C5 C26 1.3935 . . no C7 C9 1.4735 . . no C9 C14 1.3709 . . no C11 C12 1.3541 . . no C14 C15 1.4945 . . no C20 C21 1.5172 . . no C23 C24 1.4863 . . no C26 C27 1.3369 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 O16 C17 118.77 . . . yes C3 N4 C5 117.32 . . . yes C5 N6 C7 128.71 . . . yes C5 N6 C15 118.30 . . . yes C7 N6 C15 112.93 . . . yes C9 N10 C11 113.83 . . . yes C12 N13 C14 112.31 . . . yes C17 N19 C20 122.90 . . . yes C17 N19 C24 119.46 . . . yes C20 N19 C24 113.21 . . . yes C21 N22 C23 109.33 . . . yes C21 N22 C25 110.51 . . . yes C23 N22 C25 112.15 . . . yes Cl1 C2 C3 119.04 . . . yes Cl1 C2 C27 120.99 . . . yes C3 C2 C27 119.97 . . . no N4 C3 C2 122.57 . . . yes N4 C5 N6 115.40 . . . yes N4 C5 C26 122.31 . . . yes N6 C5 C26 122.29 . . . yes O8 C7 N6 126.21 . . . yes O8 C7 C9 127.98 . . . yes N6 C7 C9 105.80 . . . yes N10 C9 C7 127.63 . . . yes N10 C9 C14 123.37 . . . yes C7 C9 C14 108.94 . . . no N10 C11 C12 123.91 . . . yes N13 C12 C11 122.21 . . . yes N13 C14 C9 124.23 . . . yes N13 C14 C15 125.61 . . . yes C9 C14 C15 110.01 . . . no O16 C15 N6 108.45 . . . yes O16 C15 C14 109.35 . . . yes N6 C15 C14 101.45 . . . yes O16 C17 O18 122.04 . . . yes O16 C17 N19 112.20 . . . yes O18 C17 N19 125.74 . . . yes N19 C20 C21 111.35 . . . yes N22 C21 C20 109.63 . . . yes N22 C23 C24 110.77 . . . yes N19 C24 C23 110.28 . . . yes C5 C26 C27 119.48 . . . no C2 C27 C26 118.32 . . . no 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 C17 O16 C15 C14 110.36 . . . . no C15 O16 C17 O18 4.56 . . . . no C17 O16 C15 N6 -139.83 . . . . no C15 O16 C17 N19 -177.17 . . . . no C3 N4 C5 N6 -178.13 . . . . no C5 N4 C3 C2 0.20 . . . . no C3 N4 C5 C26 1.47 . . . . no C15 N6 C7 C9 -6.47 . . . . no C7 N6 C5 C26 9.82 . . . . no C15 N6 C5 C26 -167.15 . . . . no C7 N6 C15 O16 -105.76 . . . . no C15 N6 C5 N4 12.45 . . . . no C5 N6 C15 O16 71.67 . . . . no C5 N6 C7 O8 -2.28 . . . . no C5 N6 C7 C9 176.43 . . . . no C7 N6 C5 N4 -170.58 . . . . no C7 N6 C15 C14 9.32 . . . . no C5 N6 C15 C14 -173.25 . . . . no C15 N6 C7 O8 174.82 . . . . no C9 N10 C11 C12 3.14 . . . . no C11 N10 C9 C14 -4.41 . . . . no C11 N10 C9 C7 178.60 . . . . no C12 N13 C14 C9 -1.38 . . . . no C12 N13 C14 C15 173.86 . . . . no C14 N13 C12 C11 0.09 . . . . no C24 N19 C17 O16 176.74 . . . . no C24 N19 C20 C21 53.74 . . . . no C24 N19 C17 O18 -5.08 . . . . no C20 N19 C17 O18 -159.85 . . . . no C17 N19 C24 C23 149.09 . . . . no C20 N19 C24 C23 -53.82 . . . . no C20 N19 C17 O16 21.97 . . . . no C17 N19 C20 C21 -150.08 . . . . no C21 N22 C23 C24 -60.32 . . . . no C23 N22 C21 C20 58.96 . . . . no C25 N22 C23 C24 176.75 . . . . no C25 N22 C21 C20 -177.14 . . . . no Cl1 C2 C3 N4 177.64 . . . . no C3 C2 C27 C26 1.01 . . . . no Cl1 C2 C27 C26 -178.07 . . . . no C27 C2 C3 N4 -1.45 . . . . no N4 C5 C26 C27 -1.89 . . . . no N6 C5 C26 C27 177.68 . . . . no N6 C7 C9 N10 177.81 . . . . no O8 C7 C9 C14 179.15 . . . . no N6 C7 C9 C14 0.47 . . . . no O8 C7 C9 N10 -3.51 . . . . no N10 C9 C14 N13 3.87 . . . . no C7 C9 C14 N13 -178.65 . . . . no C7 C9 C14 C15 5.47 . . . . no N10 C9 C14 C15 -172.01 . . . . no N10 C11 C12 N13 -1.09 . . . . no N13 C14 C15 N6 175.46 . . . . no C9 C14 C15 N6 -8.73 . . . . no N13 C14 C15 O16 -70.12 . . . . no C9 C14 C15 O16 105.69 . . . . no N19 C20 C21 N22 -56.16 . . . . no N22 C23 C24 N19 56.45 . . . . no C5 C26 C27 C2 0.58 . . . . no data_ab_zopiclone _database_code_CSD 171569 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-oxo-5H-pyrrolo (3,4-b)pyrazin-5-yl)-4-methyl-1-piperazine carboxylate ; _chemical_name_common zopiclone _chemical_formula_moiety ? _chemical_formula_sum 'C17 H17 Cl N6 O3' _chemical_formula_weight 388.82 _chemical_melting_point 177 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'Cl' 'Cl' 0.1484 0.1585 '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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.50540(10) _cell_length_b 8.7686(2) _cell_length_c 35.5277(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1715.09(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6067 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_preparation 'ethylacetate solution' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.256 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV Blessing, 1997' _exptl_absorpt_correction_T_min 0.872 _exptl_absorpt_correction_T_max 0.960 _exptl_special_details ; Form III, Absolute configuration Data collected by Southampton EPSRC x-ray service. ; _diffrn_ambient_temperature 150(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 'Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7644 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0578 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3259 _reflns_number_gt 2705 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Denzo & Collect (Otwinowski & Minor, 1997; Hooft & Nonius 1988) ; _computing_cell_refinement 'Denzo & Collect' _computing_data_reduction 'Denzo & Collect' _computing_structure_solution 'SHELXS (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97' _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 w=1/[\s^2^(Fo^2^)+(0.0379P)^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 -0.04(6) _refine_ls_number_reflns 3259 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0542 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.0841 _refine_ls_wR_factor_gt 0.0790 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.001 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl -0.67784(10) -0.13327(6) -0.107051(15) 0.03290(17) Uani 1 d . . . O1 O -1.6127(3) 0.13934(19) -0.21635(4) 0.0312(4) Uani 1 d . . . O2 O -1.4442(2) 0.44611(16) -0.12718(3) 0.0236(4) Uani 1 d . . . O3 O -1.1465(3) 0.60944(17) -0.10908(4) 0.0293(4) Uani 1 d . . . N1 N -1.0154(3) 0.2357(2) -0.14382(5) 0.0261(4) Uani 1 d . . . N2 N -1.3625(3) 0.2859(2) -0.17786(5) 0.0231(4) Uani 1 d . . . N3 N -1.8397(4) 0.4481(2) -0.23325(4) 0.0297(5) Uani 1 d . . . N4 N -1.5690(3) 0.6710(2) -0.19178(5) 0.0295(5) Uani 1 d . . . N5 N -1.4376(3) 0.5305(2) -0.06781(4) 0.0232(4) Uani 1 d . . . N6 N -1.6560(3) 0.5230(2) 0.00457(4) 0.0275(5) Uani 1 d . . . C1 C -0.8581(4) 0.1380(3) -0.12818(6) 0.0272(5) Uani 1 d . . . H1 H -0.7225 0.1783 -0.1150 0.033 Uiso 1 calc R . . C2 C -0.8832(4) -0.0178(2) -0.13033(5) 0.0221(5) Uani 1 d . . . C3 C -1.0750(4) -0.0774(3) -0.15024(6) 0.0252(5) Uani 1 d . . . H3 H -1.0948 -0.1847 -0.1523 0.030 Uiso 1 calc R . . C4 C -1.2384(4) 0.0199(3) -0.16719(5) 0.0254(5) Uani 1 d . . . H4 H -1.3715 -0.0182 -0.1814 0.030 Uiso 1 calc R . . C5 C -1.2017(4) 0.1762(2) -0.16281(5) 0.0226(5) Uani 1 d . . . C6 C -1.5518(4) 0.2614(3) -0.20306(6) 0.0245(5) Uani 1 d . . . C7 C -1.6540(4) 0.4153(3) -0.21052(5) 0.0249(5) Uani 1 d . . . C8 C -1.8861(4) 0.5980(3) -0.23471(6) 0.0327(6) Uani 1 d . . . H8 H -2.0170 0.6323 -0.2499 0.039 Uiso 1 calc R . . C9 C -1.7521(4) 0.7054(3) -0.21506(6) 0.0321(6) Uani 1 d . . . H9 H -1.7926 0.8099 -0.2183 0.039 Uiso 1 calc R . . C10 C -1.5273(4) 0.5214(3) -0.19042(5) 0.0243(5) Uani 1 d . . . C11 C -1.3480(4) 0.4440(2) -0.16497(5) 0.0221(5) Uani 1 d . . . H11 H -1.1806 0.4877 -0.1668 0.027 Uiso 1 calc R . . C12 C -1.3274(4) 0.5372(2) -0.10187(6) 0.0220(5) Uani 1 d . . . C13 C -1.3562(4) 0.6346(3) -0.03820(5) 0.0281(5) Uani 1 d . . . H13A H -1.4453 0.7323 -0.0402 0.034 Uiso 1 calc R . . H13B H -1.1808 0.6560 -0.0414 0.034 Uiso 1 calc R . . C14 C -1.4003(4) 0.5650(3) 0.00000(5) 0.0310(6) Uani 1 d . . . H14A H -1.2975 0.4731 0.0030 0.037 Uiso 1 calc R . . H14B H -1.3540 0.6389 0.0198 0.037 Uiso 1 calc R . . C15 C -1.7233(4) 0.4143(2) -0.02420(6) 0.0306(6) Uani 1 d . . . H15A H -1.8954 0.3846 -0.0208 0.037 Uiso 1 calc R . . H15B H -1.6223 0.3215 -0.0216 0.037 Uiso 1 calc R . . C16 C -1.6893(4) 0.4810(3) -0.06312(6) 0.0280(5) Uani 1 d . . . H16A H -1.7295 0.4033 -0.0824 0.034 Uiso 1 calc R . . H16B H -1.7999 0.5689 -0.0666 0.034 Uiso 1 calc R . . C17 C -1.6997(5) 0.4614(3) 0.04228(6) 0.0396(6) Uani 1 d . . . H17A H -1.5998 0.3701 0.0460 0.059 Uiso 1 calc R . . H17B H -1.8717 0.4345 0.0449 0.059 Uiso 1 calc R . . H17C H -1.6569 0.5382 0.0612 0.059 Uiso 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 0.0320(3) 0.0326(3) 0.0341(3) 0.0060(3) -0.0035(3) 0.0041(3) O1 0.0311(9) 0.0329(10) 0.0295(9) -0.0061(7) -0.0071(7) -0.0028(8) O2 0.0263(8) 0.0286(8) 0.0159(7) -0.0041(7) -0.0020(7) -0.0058(7) O3 0.0280(8) 0.0340(9) 0.0260(8) 0.0020(8) -0.0036(7) -0.0074(8) N1 0.0277(10) 0.0234(10) 0.0272(10) 0.0001(9) -0.0033(9) 0.0003(9) N2 0.0265(10) 0.0232(10) 0.0197(9) -0.0008(9) -0.0039(8) 0.0016(8) N3 0.0290(10) 0.0377(12) 0.0223(10) 0.0031(9) -0.0025(9) 0.0034(10) N4 0.0339(11) 0.0316(13) 0.0228(10) 0.0009(9) -0.0008(9) 0.0035(9) N5 0.0242(10) 0.0274(11) 0.0181(9) -0.0063(8) -0.0004(8) -0.0035(9) N6 0.0303(11) 0.0337(11) 0.0185(9) -0.0021(9) 0.0002(8) 0.0019(9) C1 0.0262(12) 0.0318(13) 0.0236(11) -0.0011(11) -0.0038(10) -0.0028(12) C2 0.0232(12) 0.0228(12) 0.0205(10) 0.0031(10) 0.0012(9) 0.0033(10) C3 0.0277(12) 0.0227(13) 0.0252(11) 0.0033(10) 0.0028(10) -0.0025(11) C4 0.0277(12) 0.0278(13) 0.0207(11) -0.0021(11) 0.0000(10) -0.0044(10) C5 0.0219(12) 0.0287(14) 0.0172(11) 0.0034(10) 0.0010(10) -0.0027(10) C6 0.0237(11) 0.0325(14) 0.0174(11) -0.0026(11) 0.0012(10) -0.0022(12) C7 0.0261(12) 0.0309(13) 0.0177(10) -0.0007(10) 0.0022(10) 0.0011(11) C8 0.0322(13) 0.0417(16) 0.0242(12) 0.0053(12) 0.0003(10) 0.0065(12) C9 0.0383(14) 0.0336(14) 0.0244(12) 0.0014(12) -0.0002(11) 0.0098(12) C10 0.0269(12) 0.0283(14) 0.0178(10) 0.0006(10) 0.0024(10) 0.0013(11) C11 0.0262(11) 0.0225(12) 0.0177(10) 0.0023(10) 0.0027(10) -0.0008(10) C12 0.0246(11) 0.0189(11) 0.0226(11) 0.0004(10) -0.0075(11) 0.0032(11) C13 0.0276(12) 0.0299(12) 0.0268(12) -0.0085(11) -0.0046(10) -0.0026(11) C14 0.0335(13) 0.0370(14) 0.0223(12) -0.0064(11) -0.0066(10) 0.0045(12) C15 0.0331(13) 0.0285(13) 0.0302(13) -0.0045(11) 0.0034(11) -0.0015(12) C16 0.0250(12) 0.0341(14) 0.0248(11) -0.0069(11) -0.0003(10) -0.0054(11) C17 0.0448(16) 0.0467(16) 0.0274(12) -0.0005(12) 0.0017(12) 0.0063(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.728(2) . ? O1 C6 1.217(3) . ? O2 C12 1.364(2) . ? O2 C11 1.444(2) . ? O3 C12 1.208(2) . ? N1 C5 1.334(3) . ? N1 C1 1.339(3) . ? N2 C6 1.391(3) . ? N2 C5 1.412(2) . ? N2 C11 1.462(3) . ? N3 C7 1.335(3) . ? N3 C8 1.340(3) . ? N4 C10 1.332(3) . ? N4 C9 1.338(3) . ? N5 C12 1.355(3) . ? N5 C16 1.461(3) . ? N5 C13 1.463(3) . ? N6 C15 1.446(3) . ? N6 C14 1.464(3) . ? N6 C17 1.465(2) . ? C1 C2 1.376(3) . ? C2 C3 1.374(3) . ? C3 C4 1.379(3) . ? C4 C5 1.394(3) . ? C6 C7 1.486(3) . ? C7 C10 1.364(3) . ? C8 C9 1.385(3) . ? C10 C11 1.501(3) . ? C13 C14 1.508(3) . ? C15 C16 1.513(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 C12 O2 C11 116.59(16) . . ? C5 N1 C1 117.20(18) . . ? C6 N2 C5 127.45(18) . . ? C6 N2 C11 112.90(17) . . ? C5 N2 C11 119.53(16) . . ? C7 N3 C8 112.4(2) . . ? C10 N4 C9 111.98(19) . . ? C12 N5 C16 122.64(16) . . ? C12 N5 C13 118.53(17) . . ? C16 N5 C13 113.20(16) . . ? C15 N6 C14 109.50(17) . . ? C15 N6 C17 111.18(17) . . ? C14 N6 C17 110.61(17) . . ? N1 C1 C2 123.19(19) . . ? C3 C2 C1 118.90(19) . . ? C3 C2 Cl1 121.78(17) . . ? C1 C2 Cl1 119.31(16) . . ? C2 C3 C4 119.4(2) . . ? C3 C4 C5 117.7(2) . . ? N1 C5 C4 123.54(19) . . ? N1 C5 N2 114.01(17) . . ? C4 C5 N2 122.44(19) . . ? O1 C6 N2 126.3(2) . . ? O1 C6 C7 128.71(19) . . ? N2 C6 C7 104.95(19) . . ? N3 C7 C10 124.1(2) . . ? N3 C7 C6 126.4(2) . . ? C10 C7 C6 109.44(18) . . ? N3 C8 C9 123.1(2) . . ? N4 C9 C8 124.0(2) . . ? N4 C10 C7 124.4(2) . . ? N4 C10 C11 125.5(2) . . ? C7 C10 C11 110.06(19) . . ? O2 C11 N2 106.45(16) . . ? O2 C11 C10 108.23(17) . . ? N2 C11 C10 101.78(17) . . ? O3 C12 N5 125.6(2) . . ? O3 C12 O2 123.78(19) . . ? N5 C12 O2 110.62(17) . . ? N5 C13 C14 110.19(18) . . ? N6 C14 C13 110.87(17) . . ? N6 C15 C16 111.08(17) . . ? N5 C16 C15 109.67(18) . . ? 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 C5 N1 C1 C2 -1.2(3) . . . . ? N1 C1 C2 C3 1.7(3) . . . . ? N1 C1 C2 Cl1 -176.70(15) . . . . ? C1 C2 C3 C4 -0.7(3) . . . . ? Cl1 C2 C3 C4 177.73(15) . . . . ? C2 C3 C4 C5 -0.8(3) . . . . ? C1 N1 C5 C4 -0.4(3) . . . . ? C1 N1 C5 N2 178.80(16) . . . . ? C3 C4 C5 N1 1.4(3) . . . . ? C3 C4 C5 N2 -177.76(17) . . . . ? C6 N2 C5 N1 170.32(18) . . . . ? C11 N2 C5 N1 -13.8(2) . . . . ? C6 N2 C5 C4 -10.5(3) . . . . ? C11 N2 C5 C4 165.42(19) . . . . ? C5 N2 C6 O1 0.6(3) . . . . ? C11 N2 C6 O1 -175.54(19) . . . . ? C5 N2 C6 C7 -177.83(17) . . . . ? C11 N2 C6 C7 6.0(2) . . . . ? C8 N3 C7 C10 1.1(3) . . . . ? C8 N3 C7 C6 -178.69(19) . . . . ? O1 C6 C7 N3 1.5(4) . . . . ? N2 C6 C7 N3 179.85(19) . . . . ? O1 C6 C7 C10 -178.3(2) . . . . ? N2 C6 C7 C10 0.1(2) . . . . ? C7 N3 C8 C9 0.9(3) . . . . ? C10 N4 C9 C8 1.4(3) . . . . ? N3 C8 C9 N4 -2.3(3) . . . . ? C9 N4 C10 C7 0.5(3) . . . . ? C9 N4 C10 C11 -175.13(18) . . . . ? N3 C7 C10 N4 -1.9(3) . . . . ? C6 C7 C10 N4 177.90(19) . . . . ? N3 C7 C10 C11 174.34(18) . . . . ? C6 C7 C10 C11 -5.9(2) . . . . ? C12 O2 C11 N2 140.39(17) . . . . ? C12 O2 C11 C10 -110.87(19) . . . . ? C6 N2 C11 O2 104.11(18) . . . . ? C5 N2 C11 O2 -72.4(2) . . . . ? C6 N2 C11 C10 -9.1(2) . . . . ? C5 N2 C11 C10 174.38(16) . . . . ? N4 C10 C11 O2 73.2(3) . . . . ? C7 C10 C11 O2 -103.0(2) . . . . ? N4 C10 C11 N2 -174.9(2) . . . . ? C7 C10 C11 N2 8.9(2) . . . . ? C16 N5 C12 O3 161.1(2) . . . . ? C13 N5 C12 O3 9.4(3) . . . . ? C16 N5 C12 O2 -21.0(3) . . . . ? C13 N5 C12 O2 -172.73(17) . . . . ? C11 O2 C12 O3 -2.9(3) . . . . ? C11 O2 C12 N5 179.11(16) . . . . ? C12 N5 C13 C14 -152.10(18) . . . . ? C16 N5 C13 C14 53.6(2) . . . . ? C15 N6 C14 C13 59.5(2) . . . . ? C17 N6 C14 C13 -177.63(17) . . . . ? N5 C13 C14 N6 -55.7(2) . . . . ? C14 N6 C15 C16 -60.2(2) . . . . ? C17 N6 C15 C16 177.3(2) . . . . ? C12 N5 C16 C15 153.09(19) . . . . ? C13 N5 C16 C15 -53.8(2) . . . . ? N6 C15 C16 N5 56.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 0.339 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.050 data_box_zopiclone _database_code_CSD 171570 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-oxo-5H-pyrrolo(3,4-b)pyrazin-5-yl) -4-methyl-1-piperazine carboxylate ; _chemical_name_common zopiclone _chemical_formula_moiety ? _chemical_formula_sum 'C17 H17 Cl N6 O3' _chemical_formula_weight 388.82 _chemical_melting_point 177? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'Cl' 'Cl' 0.1484 0.1585 '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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.50230(10) _cell_length_b 8.7676(2) _cell_length_c 35.5314(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1714.10(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6228 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 26.37 _exptl_crystal_description 'box' _exptl_crystal_colour 'clear' _exptl_crystal_preparation 'ethylacetate solution' _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.507 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.257 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV Blessing, 1997' _exptl_absorpt_correction_T_min 0.913 _exptl_absorpt_correction_T_max 0.989 _exptl_special_details ; >From III, Absolute configuration Data collected by Southampton EPSRC x-ray service. ; _diffrn_ambient_temperature 150(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 'Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8033 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0575 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 26.38 _reflns_number_total 3302 _reflns_number_gt 2835 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Denzo & Collect (Otwinowski & Minor, 1997; Hooft & Nonius 1988) ; _computing_cell_refinement 'Denzo & Collect' _computing_data_reduction 'Denzo & Collect' _computing_structure_solution 'SHELXS (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97' _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 w=1/[\s^2^(Fo^2^)+(0.0337P)^2^+0.0876P] 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 -0.04(6) _refine_ls_number_reflns 3302 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0493 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0844 _refine_ls_wR_factor_gt 0.0794 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.001 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.67746(10) 0.13352(6) 0.107020(15) 0.03236(16) Uani 1 d . . . O1 O 1.6127(3) -0.13955(18) 0.21631(4) 0.0306(4) Uani 1 d . . . O2 O 1.4437(3) -0.44562(16) 0.12715(3) 0.0240(3) Uani 1 d . . . O3 O 1.1458(3) -0.60957(16) 0.10917(4) 0.0285(4) Uani 1 d . . . N1 N 1.0148(3) -0.2352(2) 0.14383(5) 0.0263(4) Uani 1 d . . . N2 N 1.3618(3) -0.28569(19) 0.17784(4) 0.0227(4) Uani 1 d . . . N3 N 1.8395(4) -0.4480(2) 0.23332(4) 0.0296(5) Uani 1 d . . . N4 N 1.5690(4) -0.6711(2) 0.19180(5) 0.0291(5) Uani 1 d . . . N5 N 1.4375(3) -0.5303(2) 0.06779(4) 0.0236(4) Uani 1 d . . . N6 N 1.6563(3) -0.5232(2) -0.00463(4) 0.0267(4) Uani 1 d . . . C1 C 0.8579(4) -0.1380(2) 0.12812(5) 0.0260(5) Uani 1 d . . . H1 H 0.7227 -0.1783 0.1148 0.031 Uiso 1 calc R . . C2 C 0.8828(4) 0.0173(2) 0.13034(5) 0.0233(5) Uani 1 d . . . C3 C 1.0750(4) 0.0778(2) 0.15022(5) 0.0262(5) Uani 1 d . . . H3 H 1.0952 0.1851 0.1522 0.031 Uiso 1 calc R . . C4 C 1.2376(4) -0.0201(2) 0.16722(5) 0.0247(5) Uani 1 d . . . H4 H 1.3704 0.0179 0.1815 0.030 Uiso 1 calc R . . C5 C 1.2012(4) -0.1757(2) 0.16282(5) 0.0225(5) Uani 1 d . . . C6 C 1.5517(4) -0.2616(3) 0.20312(5) 0.0247(5) Uani 1 d . . . C7 C 1.6545(4) -0.4153(2) 0.21054(5) 0.0241(5) Uani 1 d . . . C8 C 1.8858(4) -0.5985(3) 0.23474(6) 0.0330(6) Uani 1 d . . . H8 H 2.0170 -0.6326 0.2500 0.040 Uiso 1 calc R . . C9 C 1.7521(4) -0.7061(3) 0.21516(6) 0.0334(6) Uani 1 d . . . H9 H 1.7923 -0.8106 0.2185 0.040 Uiso 1 calc R . . C10 C 1.5278(4) -0.5216(2) 0.19032(5) 0.0241(5) Uani 1 d . . . C11 C 1.3477(4) -0.4443(2) 0.16496(5) 0.0225(5) Uani 1 d . . . H11 H 1.1804 -0.4883 0.1668 0.027 Uiso 1 calc R . . C12 C 1.3268(4) -0.5370(2) 0.10180(5) 0.0219(5) Uani 1 d . . . C13 C 1.3550(4) -0.6350(2) 0.03813(5) 0.0278(5) Uani 1 d . . . H13A H 1.1793 -0.6558 0.0412 0.033 Uiso 1 calc R . . H13B H 1.4436 -0.7329 0.0402 0.033 Uiso 1 calc R . . C14 C 1.4006(4) -0.5649(3) 0.00003(5) 0.0310(6) Uani 1 d . . . H14A H 1.3539 -0.6385 -0.0198 0.037 Uiso 1 calc R . . H14B H 1.2982 -0.4728 -0.0029 0.037 Uiso 1 calc R . . C15 C 1.7238(4) -0.4139(2) 0.02418(5) 0.0296(6) Uani 1 d . . . H15A H 1.6227 -0.3211 0.0216 0.036 Uiso 1 calc R . . H15B H 1.8960 -0.3841 0.0208 0.036 Uiso 1 calc R . . C16 C 1.6894(4) -0.4810(3) 0.06304(5) 0.0271(5) Uani 1 d . . . H16A H 1.7998 -0.5691 0.0664 0.033 Uiso 1 calc R . . H16B H 1.7300 -0.4036 0.0823 0.033 Uiso 1 calc R . . C17 C 1.7007(5) -0.4614(3) -0.04231(6) 0.0383(6) Uani 1 d . . . H17A H 1.6041 -0.3686 -0.0458 0.057 Uiso 1 calc R . . H17B H 1.6541 -0.5372 -0.0612 0.057 Uiso 1 calc R . . H17C H 1.8737 -0.4371 -0.0450 0.057 Uiso 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 0.0307(3) 0.0308(3) 0.0356(3) 0.0059(3) -0.0038(3) 0.0043(3) O1 0.0311(10) 0.0312(9) 0.0296(8) -0.0059(7) -0.0068(7) -0.0031(8) O2 0.0255(8) 0.0285(8) 0.0178(7) -0.0044(6) -0.0014(6) -0.0053(7) O3 0.0265(9) 0.0311(8) 0.0281(8) 0.0006(7) -0.0037(7) -0.0078(8) N1 0.0259(11) 0.0227(9) 0.0301(10) -0.0011(8) -0.0034(9) -0.0011(9) N2 0.0247(10) 0.0215(9) 0.0220(8) -0.0021(8) -0.0035(8) 0.0023(9) N3 0.0263(11) 0.0378(11) 0.0247(9) 0.0031(8) -0.0032(9) 0.0021(10) N4 0.0336(12) 0.0295(11) 0.0242(9) 0.0012(8) -0.0007(9) 0.0017(9) N5 0.0230(11) 0.0274(10) 0.0203(9) -0.0047(7) -0.0012(8) -0.0047(9) N6 0.0272(11) 0.0319(10) 0.0210(9) -0.0016(8) -0.0005(8) 0.0012(9) C1 0.0233(12) 0.0284(12) 0.0264(11) 0.0012(9) -0.0044(10) -0.0015(12) C2 0.0205(13) 0.0265(11) 0.0229(10) 0.0029(9) 0.0020(9) 0.0051(10) C3 0.0293(13) 0.0234(11) 0.0258(11) 0.0020(9) 0.0028(10) -0.0040(11) C4 0.0258(13) 0.0262(11) 0.0222(10) -0.0021(10) -0.0007(9) -0.0038(11) C5 0.0230(13) 0.0249(11) 0.0196(10) 0.0027(9) -0.0007(10) 0.0002(11) C6 0.0229(12) 0.0316(13) 0.0198(11) -0.0014(10) -0.0004(10) -0.0001(12) C7 0.0236(12) 0.0296(12) 0.0190(10) 0.0006(9) 0.0010(10) 0.0001(11) C8 0.0302(15) 0.0440(15) 0.0247(12) 0.0060(10) -0.0003(10) 0.0071(13) C9 0.0390(16) 0.0346(13) 0.0266(12) 0.0017(11) -0.0012(11) 0.0103(13) C10 0.0252(13) 0.0279(12) 0.0193(10) 0.0004(9) 0.0029(9) 0.0027(11) C11 0.0251(12) 0.0223(11) 0.0202(10) 0.0015(9) 0.0018(9) -0.0008(11) C12 0.0211(12) 0.0188(10) 0.0257(10) 0.0001(9) -0.0070(10) 0.0026(11) C13 0.0250(13) 0.0287(11) 0.0296(11) -0.0084(10) -0.0048(10) -0.0039(12) C14 0.0344(14) 0.0347(13) 0.0239(11) -0.0050(10) -0.0044(10) 0.0045(12) C15 0.0302(14) 0.0250(11) 0.0335(12) -0.0045(10) 0.0044(10) -0.0015(11) C16 0.0219(13) 0.0341(13) 0.0254(10) -0.0065(10) 0.0002(10) -0.0049(12) C17 0.0427(16) 0.0445(14) 0.0277(11) 0.0003(11) 0.0029(11) 0.0074(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.733(2) . ? O1 C6 1.215(3) . ? O2 C12 1.366(2) . ? O2 C11 1.444(2) . ? O3 C12 1.210(2) . ? N1 C5 1.334(3) . ? N1 C1 1.336(3) . ? N2 C6 1.394(3) . ? N2 C5 1.413(2) . ? N2 C11 1.466(3) . ? N3 C7 1.332(3) . ? N3 C8 1.344(3) . ? N4 C10 1.331(3) . ? N4 C9 1.341(3) . ? N5 C12 1.355(3) . ? N5 C16 1.461(3) . ? N5 C13 1.469(2) . ? N6 C15 1.450(2) . ? N6 C14 1.463(3) . ? N6 C17 1.465(2) . ? C1 C2 1.370(3) . ? C2 C3 1.378(3) . ? C3 C4 1.379(3) . ? C4 C5 1.388(3) . ? C6 C7 1.485(3) . ? C7 C10 1.368(3) . ? C8 C9 1.384(3) . ? C10 C11 1.501(3) . ? C13 C14 1.508(3) . ? C15 C16 1.513(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 C12 O2 C11 116.47(16) . . ? C5 N1 C1 117.30(17) . . ? C6 N2 C5 127.48(17) . . ? C6 N2 C11 112.63(17) . . ? C5 N2 C11 119.78(16) . . ? C7 N3 C8 112.3(2) . . ? C10 N4 C9 112.21(19) . . ? C12 N5 C16 122.84(16) . . ? C12 N5 C13 118.30(17) . . ? C16 N5 C13 113.27(16) . . ? C15 N6 C14 109.36(16) . . ? C15 N6 C17 111.00(17) . . ? C14 N6 C17 110.87(17) . . ? N1 C1 C2 123.0(2) . . ? C1 C2 C3 119.25(19) . . ? C1 C2 Cl1 119.44(17) . . ? C3 C2 Cl1 121.28(16) . . ? C2 C3 C4 118.88(19) . . ? C3 C4 C5 117.9(2) . . ? N1 C5 C4 123.55(19) . . ? N1 C5 N2 113.87(17) . . ? C4 C5 N2 122.57(19) . . ? O1 C6 N2 126.1(2) . . ? O1 C6 C7 128.69(19) . . ? N2 C6 C7 105.20(18) . . ? N3 C7 C10 124.2(2) . . ? N3 C7 C6 126.49(19) . . ? C10 C7 C6 109.33(18) . . ? N3 C8 C9 123.3(2) . . ? N4 C9 C8 123.7(2) . . ? N4 C10 C7 124.3(2) . . ? N4 C10 C11 125.5(2) . . ? C7 C10 C11 110.11(18) . . ? O2 C11 N2 106.20(15) . . ? O2 C11 C10 108.25(17) . . ? N2 C11 C10 101.90(16) . . ? O3 C12 N5 125.85(19) . . ? O3 C12 O2 123.59(18) . . ? N5 C12 O2 110.54(18) . . ? N5 C13 C14 109.77(17) . . ? N6 C14 C13 111.31(17) . . ? N6 C15 C16 110.83(17) . . ? N5 C16 C15 109.84(18) . . ? 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 C5 N1 C1 C2 0.9(3) . . . . ? N1 C1 C2 C3 -1.3(3) . . . . ? N1 C1 C2 Cl1 176.84(15) . . . . ? C1 C2 C3 C4 0.2(3) . . . . ? Cl1 C2 C3 C4 -177.88(15) . . . . ? C2 C3 C4 C5 1.1(3) . . . . ? C1 N1 C5 C4 0.6(3) . . . . ? C1 N1 C5 N2 -178.63(16) . . . . ? C3 C4 C5 N1 -1.7(3) . . . . ? C3 C4 C5 N2 177.56(18) . . . . ? C6 N2 C5 N1 -170.29(18) . . . . ? C11 N2 C5 N1 13.8(2) . . . . ? C6 N2 C5 C4 10.4(3) . . . . ? C11 N2 C5 C4 -165.44(19) . . . . ? C5 N2 C6 O1 -0.8(3) . . . . ? C11 N2 C6 O1 175.4(2) . . . . ? C5 N2 C6 C7 177.97(18) . . . . ? C11 N2 C6 C7 -5.9(2) . . . . ? C8 N3 C7 C10 -1.0(3) . . . . ? C8 N3 C7 C6 178.5(2) . . . . ? O1 C6 C7 N3 -0.9(4) . . . . ? N2 C6 C7 N3 -179.61(19) . . . . ? O1 C6 C7 C10 178.7(2) . . . . ? N2 C6 C7 C10 0.0(2) . . . . ? C7 N3 C8 C9 -1.1(3) . . . . ? C10 N4 C9 C8 -1.4(3) . . . . ? N3 C8 C9 N4 2.5(3) . . . . ? C9 N4 C10 C7 -0.8(3) . . . . ? C9 N4 C10 C11 175.54(18) . . . . ? N3 C7 C10 N4 2.1(4) . . . . ? C6 C7 C10 N4 -177.5(2) . . . . ? N3 C7 C10 C11 -174.69(19) . . . . ? C6 C7 C10 C11 5.7(2) . . . . ? C12 O2 C11 N2 -140.40(17) . . . . ? C12 O2 C11 C10 110.81(19) . . . . ? C6 N2 C11 O2 -104.31(18) . . . . ? C5 N2 C11 O2 72.1(2) . . . . ? C6 N2 C11 C10 8.9(2) . . . . ? C5 N2 C11 C10 -174.62(16) . . . . ? N4 C10 C11 O2 -73.8(3) . . . . ? C7 C10 C11 O2 103.0(2) . . . . ? N4 C10 C11 N2 174.5(2) . . . . ? C7 C10 C11 N2 -8.7(2) . . . . ? C16 N5 C12 O3 -160.8(2) . . . . ? C13 N5 C12 O3 -9.0(3) . . . . ? C16 N5 C12 O2 21.0(3) . . . . ? C13 N5 C12 O2 172.85(16) . . . . ? C11 O2 C12 O3 3.0(3) . . . . ? C11 O2 C12 N5 -178.71(16) . . . . ? C12 N5 C13 C14 152.20(19) . . . . ? C16 N5 C13 C14 -53.4(2) . . . . ? C15 N6 C14 C13 -59.8(2) . . . . ? C17 N6 C14 C13 177.52(17) . . . . ? N5 C13 C14 N6 55.6(2) . . . . ? C14 N6 C15 C16 60.2(2) . . . . ? C17 N6 C15 C16 -177.2(2) . . . . ? C12 N5 C16 C15 -152.86(19) . . . . ? C13 N5 C16 C15 54.1(2) . . . . ? N6 C15 C16 N5 -57.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.273 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.048 data_Zopiclone_dihydrate _database_code_CSD 171571 #------------------------------------------------------------------------------ _audit_creation_date 'Tue Jul 13 13:38:34 1999' _audit_creation_method 'from TEXRAY.INF file' _audit_update_record 'line edit July 2001' #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan' _computing_structure_solution 'SIR' _computing_structure_refinement 'teXsan' _computing_publication_material 'teXsan' #------------------------------------------------------------------------------ _cell_length_a 16.374(4) _cell_length_b 7.030(3) _cell_length_c 17.185(2) _cell_angle_alpha 90 _cell_angle_beta 108.62(1) _cell_angle_gamma 90 _cell_volume 1874.7(9) _cell_formula_units_Z 4 _cell_measurement_temperature 123 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.9 _cell_measurement_theta_max 16.1 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x,1/2+y,1/2-z' ' -x, -y, -z' ' +x,1/2-y,1/2+z' #------------------------------------------------------------------------------ _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_preparation 'toluene solution' _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.505 _exptl_crystal_density_meas ? _chemical_formula_weight 424.84 _chemical_formula_analytical ? _chemical_formula_sum 'C17 H21 Cl N6 O5 ' _chemical_formula_moiety '?' _chemical_formula_structural ? _chemical_compound_source ? _chemical_melting_point ? _chemical_name_systematic ; (6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-oxo -5H-pyrrolo(3,4-b)pyrazin-5-yl)-4-methyl-1-piperazine carboxylate dihydrate ; _chemical_name_common 'zopiclone dihydrate' _exptl_crystal_F_000 888.00 _exptl_absorpt_coefficient_mu 0.249 _exptl_absorpt_correction_type none _exptl_special_details ; Form I ; #------------------------------------------------------------------------------ _diffrn_special_details none _diffrn_ambient_temperature 123 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoKalpha _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector ? _diffrn_measurement_device 'Rigaku AFC7S' _diffrn_measurement_method 'omega/2-theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -0.87 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? ? ? ? ? ? ? _diffrn_reflns_number 4577 _reflns_number_total 4427 _reflns_number_observed 2967 _reflns_observed_criterion 'I>2.00\s(I)' _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 27.02 _diffrn_reflns_reduction_process 'texsan' _diffrn_orient_matrix_UB_11 0.01527 _diffrn_orient_matrix_UB_12 0.02632 _diffrn_orient_matrix_UB_13 0.06014 _diffrn_orient_matrix_UB_21 0.05184 _diffrn_orient_matrix_UB_22 0.07301 _diffrn_orient_matrix_UB_23 -0.00165 _diffrn_orient_matrix_UB_31 -0.03511 _diffrn_orient_matrix_UB_32 0.11921 _diffrn_orient_matrix_UB_33 -0.01226 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 68 0.003 0.002 'International Tables' H 0 84 0.000 0.000 'International Tables' Cl 0 4 0.148 0.159 'International Tables' N 0 24 0.006 0.003 'International Tables' O 0 20 0.011 0.006 'International Tables' #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom Cl(1) 0.32666(3) 0.51653(9) 0.78951(3) 0.0304 Uij ? ? O(1) -0.05583(9) 0.2021(2) 0.51841(9) 0.0250 Uij ? ? O(2) 0.15230(8) 0.1558(2) 0.41374(8) 0.0175 Uij ? ? O(3) 0.25585(9) 0.3537(2) 0.39900(8) 0.0213 Uij ? ? O(4) 0.39850(10) 0.5946(2) 0.41334(9) 0.0275 Uij ? ? O(5) 0.4556(1) 0.6112(2) 0.58572(10) 0.0292 Uij ? ? N(1) 0.1979(1) 0.4132(2) 0.55650(10) 0.0168 Uij ? ? N(2) 0.06502(10) 0.2932(2) 0.48418(10) 0.0163 Uij ? ? N(3) -0.1339(1) 0.1635(2) 0.3330(1) 0.0226 Uij ? ? N(4) -0.0041(1) 0.2768(2) 0.26323(10) 0.0203 Uij ? ? N(5) 0.2911(1) 0.0806(2) 0.47523(10) 0.0190 Uij ? ? N(6) 0.4025(1) -0.0343(2) 0.63280(10) 0.0177 Uij ? ? C(1) 0.2585(1) 0.4620(3) 0.6263(1) 0.0182 Uij ? ? C(2) 0.2474(1) 0.4385(3) 0.7021(1) 0.0193 Uij ? ? C(3) 0.1722(1) 0.3577(3) 0.7071(1) 0.0209 Uij ? ? C(4) 0.1089(1) 0.3058(3) 0.6355(1) 0.0189 Uij ? ? C(5) 0.1251(1) 0.3381(3) 0.5616(1) 0.0160 Uij ? ? C(6) -0.0189(1) 0.2304(3) 0.4685(1) 0.0181 Uij ? ? C(7) -0.0540(1) 0.2142(3) 0.3769(1) 0.0176 Uij ? ? C(8) -0.1474(1) 0.1717(3) 0.2518(1) 0.0253 Uij ? ? C(9) -0.0847(1) 0.2302(3) 0.2178(1) 0.0234 Uij ? ? C(10) 0.0090(1) 0.2640(3) 0.3437(1) 0.0168 Uij ? ? C(11) 0.0922(1) 0.3048(3) 0.4105(1) 0.0155 Uij ? ? C(12) 0.2373(1) 0.2111(3) 0.4294(1) 0.0175 Uij ? ? C(13) 0.3848(1) 0.1008(3) 0.4958(1) 0.0207 Uij ? ? C(14) 0.4253(1) 0.1257(3) 0.5884(1) 0.0195 Uij ? ? C(15) 0.3084(1) -0.0474(3) 0.6114(1) 0.0192 Uij ? ? C(16) 0.2663(1) -0.0758(3) 0.5196(1) 0.0201 Uij ? ? C(17) 0.4403(1) -0.0059(3) 0.7219(1) 0.0254 Uij ? ? H(1) 0.3092 0.5125 0.6192 0.015(5) Uij ? ? H(2) 0.1636 0.3387 0.7592 0.023(6) Uij ? ? H(3) 0.0589 0.2513 0.6376 0.041(7) Uij ? ? H(4) -0.2021 0.1341 0.2167 0.033(7) Uij ? ? H(5) -0.1000 0.2407 0.1564 0.028(6) Uij ? ? H(6) 0.1159 0.4338 0.4061 0.011(5) Uij ? ? H(7) 0.3968 0.2094 0.4673 0.021(6) Uij ? ? H(8) 0.4103 -0.0165 0.4778 0.019(5) Uij ? ? H(9) 0.4878 0.1315 0.6012 0.022(6) Uij ? ? H(10) 0.4053 0.2501 0.6063 0.019(5) Uij ? ? H(11) 0.2944 -0.1573 0.6402 0.020(5) Uij ? ? H(12) 0.2846 0.0733 0.6285 0.019(5) Uij ? ? H(13) 0.2865 -0.1942 0.5011 0.014(5) Uij ? ? H(14) 0.2034 -0.0808 0.5071 0.022(6) Uij ? ? H(15) 0.4206 0.1087 0.7413 0.026(6) Uij ? ? H(16) 0.4270 -0.1145 0.7548 0.036(7) Uij ? ? H(17) 0.5033 0.0015 0.7357 0.034(7) Uij ? ? H(18) 0.4391 0.5282 0.4050 0.056(9) Uij ? ? H(19) 0.3581 0.5229 0.4054 0.047(9) Uij ? ? H(20) 0.4356 0.6172 0.5363 0.049(8) Uij ? ? H(21) 0.4462 0.7225 0.6033 0.048(8) Uij ? ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl(1) 0.0255(3) 0.0439(3) 0.0181(2) -0.0099(2) 0.0014(2) -0.0050(2) O(1) 0.0190(7) 0.0338(9) 0.0242(7) -0.0049(6) 0.0096(6) 0.0024(6) O(2) 0.0121(6) 0.0190(7) 0.0204(7) 0.0016(5) 0.0040(5) -0.0002(6) O(3) 0.0180(7) 0.0258(8) 0.0209(7) 0.0007(6) 0.0074(6) 0.0072(6) O(4) 0.0238(8) 0.0257(8) 0.0316(8) -0.0007(7) 0.0069(7) 0.0024(7) O(5) 0.0360(9) 0.0233(8) 0.0266(9) 0.0071(7) 0.0074(7) -0.0017(6) N(1) 0.0164(8) 0.0148(8) 0.0190(8) -0.0010(6) 0.0054(6) -0.0010(6) N(2) 0.0145(8) 0.0182(8) 0.0161(8) -0.0022(6) 0.0048(6) -0.0001(6) N(3) 0.0163(8) 0.0207(9) 0.0276(9) -0.0010(7) 0.0024(7) -0.0038(7) N(4) 0.0190(8) 0.0214(9) 0.0185(9) 0.0036(7) 0.0032(7) -0.0024(7) N(5) 0.0140(8) 0.0232(9) 0.0189(8) 0.0010(7) 0.0040(7) 0.0043(7) N(6) 0.0165(8) 0.0176(8) 0.0183(8) 0.0000(7) 0.0043(7) 0.0022(7) C(1) 0.0169(9) 0.0149(9) 0.0223(10) -0.0010(8) 0.0057(8) -0.0014(8) C(2) 0.021(1) 0.0184(10) 0.0164(9) -0.0004(8) 0.0022(8) -0.0029(8) C(3) 0.023(1) 0.023(1) 0.0163(9) -0.0010(8) 0.0055(8) 0.0019(8) C(4) 0.0188(10) 0.0187(10) 0.0198(9) -0.0022(8) 0.0070(8) 0.0014(8) C(5) 0.0174(9) 0.0120(9) 0.0173(9) 0.0014(7) 0.0037(7) -0.0003(7) C(6) 0.0144(9) 0.0158(9) 0.0232(10) 0.0004(8) 0.0048(8) 0.0007(8) C(7) 0.0170(10) 0.0146(9) 0.0202(10) 0.0014(7) 0.0047(8) -0.0005(7) C(8) 0.019(1) 0.025(1) 0.027(1) -0.0004(9) -0.0008(8) -0.0091(9) C(9) 0.022(1) 0.023(1) 0.0197(10) 0.0046(9) -0.0010(8) -0.0056(8) C(10) 0.0150(9) 0.0143(9) 0.0191(9) 0.0029(7) 0.0029(7) -0.0006(7) C(11) 0.0144(9) 0.0163(9) 0.0157(9) 0.0016(7) 0.0045(7) 0.0019(7) C(12) 0.0155(9) 0.023(1) 0.0135(9) 0.0000(8) 0.0043(7) -0.0023(8) C(13) 0.0142(9) 0.025(1) 0.0224(10) 0.0027(8) 0.0055(8) 0.0074(8) C(14) 0.0146(9) 0.020(1) 0.0220(10) -0.0012(8) 0.0039(8) 0.0023(8) C(15) 0.0187(10) 0.0170(10) 0.0232(10) 0.0003(8) 0.0087(8) 0.0033(8) C(16) 0.0178(10) 0.0183(10) 0.024(1) -0.0015(8) 0.0063(8) 0.0033(8) C(17) 0.029(1) 0.026(1) 0.0185(10) 0.0011(9) 0.0042(8) -0.0012(9) #------------------------------------------------------------------------------ _refine_special_details ? _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme '1/\s^2^(F)' _refine_ls_hydrogen_treatment refU _refine_ls_extinction_method Zachariasen_type_2_Gaussian_isotropic _refine_ls_extinction_coef '0.40(11)x10^-6^' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2967 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_obs 0.0366 _refine_ls_R_factor_all 0.0719 _refine_ls_wR_factor_obs 0.0450 _refine_ls_wR_factor_all 0.0502 _refine_ls_goodness_of_fit_all ? _refine_ls_goodness_of_fit_obs 1.370 _refine_ls_shift/esd_max 0.0000 _refine_ls_shift/esd_mean ? _refine_diff_density_min -0.26 _refine_diff_density_max 0.27 #------------------------------------------------------------------------------ _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl(1) C(2) 1.731(2) ? ? yes O(1) C(6) 1.213(2) ? ? yes O(2) C(11) 1.427(2) ? ? yes O(2) C(12) 1.387(2) ? ? yes O(3) C(12) 1.213(2) ? ? yes O(4) H(18) 0.861(2) ? ? no O(4) H(19) 0.807(2) ? ? no O(5) H(20) 0.808(2) ? ? no O(5) H(21) 0.870(2) ? ? no N(1) C(1) 1.335(2) ? ? yes N(1) C(5) 1.332(2) ? ? yes N(2) C(5) 1.415(2) ? ? yes N(2) C(6) 1.386(2) ? ? yes N(2) C(11) 1.471(2) ? ? yes N(3) C(7) 1.334(2) ? ? yes N(3) C(8) 1.342(3) ? ? yes N(4) C(9) 1.342(3) ? ? yes N(4) C(10) 1.333(3) ? ? yes N(5) C(12) 1.340(2) ? ? yes N(5) C(13) 1.467(2) ? ? yes N(5) C(16) 1.467(3) ? ? yes N(6) C(14) 1.473(3) ? ? yes N(6) C(15) 1.468(2) ? ? yes N(6) C(17) 1.470(3) ? ? yes C(1) C(2) 1.381(3) ? ? yes C(1) H(1) 0.945(2) ? ? no C(2) C(3) 1.384(3) ? ? yes C(3) C(4) 1.381(3) ? ? yes C(3) H(2) 0.958(2) ? ? no C(4) C(5) 1.396(3) ? ? yes C(4) H(3) 0.915(2) ? ? no C(6) C(7) 1.498(3) ? ? yes C(7) C(10) 1.374(3) ? ? yes C(8) C(9) 1.395(3) ? ? yes C(8) H(4) 0.944(2) ? ? no C(9) H(5) 1.007(2) ? ? no C(10) C(11) 1.502(3) ? ? yes C(11) H(6) 0.999(2) ? ? no C(13) C(14) 1.526(3) ? ? yes C(13) H(7) 0.961(2) ? ? no C(13) H(8) 1.016(2) ? ? no C(14) H(9) 0.976(2) ? ? no C(14) H(10) 1.015(2) ? ? no C(15) C(16) 1.520(3) ? ? yes C(15) H(11) 0.983(2) ? ? no C(15) H(12) 1.015(2) ? ? no C(16) H(13) 0.985(2) ? ? no C(16) H(14) 0.983(2) ? ? no C(17) H(15) 0.966(2) ? ? no C(17) H(16) 1.015(2) ? ? no C(17) H(17) 0.982(2) ? ? no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(11) O(2) C(12) 116.1(1) ? ? ? yes C(1) N(1) C(5) 117.9(2) ? ? ? yes C(5) N(2) C(6) 127.0(2) ? ? ? yes C(5) N(2) C(11) 119.1(2) ? ? ? yes C(6) N(2) C(11) 113.8(2) ? ? ? yes C(7) N(3) C(8) 112.5(2) ? ? ? yes C(9) N(4) C(10) 112.9(2) ? ? ? yes C(12) N(5) C(13) 121.1(2) ? ? ? yes C(12) N(5) C(16) 125.4(2) ? ? ? yes C(13) N(5) C(16) 112.9(2) ? ? ? yes C(14) N(6) C(15) 109.7(1) ? ? ? yes C(14) N(6) C(17) 110.1(2) ? ? ? yes C(15) N(6) C(17) 109.2(2) ? ? ? yes N(1) C(1) C(2) 122.2(2) ? ? ? yes Cl(1) C(2) C(1) 119.5(2) ? ? ? yes Cl(1) C(2) C(3) 120.8(2) ? ? ? yes C(1) C(2) C(3) 119.7(2) ? ? ? yes C(2) C(3) C(4) 118.9(2) ? ? ? yes C(3) C(4) C(5) 117.5(2) ? ? ? yes N(1) C(5) N(2) 113.2(2) ? ? ? yes N(1) C(5) C(4) 123.9(2) ? ? ? yes N(2) C(5) C(4) 122.8(2) ? ? ? yes O(1) C(6) N(2) 127.0(2) ? ? ? yes O(1) C(6) C(7) 128.3(2) ? ? ? yes N(2) C(6) C(7) 104.6(2) ? ? ? yes N(3) C(7) C(6) 126.4(2) ? ? ? yes N(3) C(7) C(10) 124.4(2) ? ? ? yes C(6) C(7) C(10) 109.3(2) ? ? ? yes N(3) C(8) C(9) 123.3(2) ? ? ? yes N(4) C(9) C(8) 123.2(2) ? ? ? yes N(4) C(10) C(7) 123.7(2) ? ? ? yes N(4) C(10) C(11) 125.9(2) ? ? ? yes C(7) C(10) C(11) 110.4(2) ? ? ? yes O(2) C(11) N(2) 108.7(1) ? ? ? yes O(2) C(11) C(10) 109.6(1) ? ? ? yes N(2) C(11) C(10) 101.4(1) ? ? ? yes O(2) C(12) O(3) 121.5(2) ? ? ? yes O(2) C(12) N(5) 110.7(2) ? ? ? yes O(3) C(12) N(5) 127.7(2) ? ? ? yes N(5) C(13) C(14) 109.6(2) ? ? ? yes N(6) C(14) C(13) 110.8(2) ? ? ? yes N(6) C(15) C(16) 111.1(2) ? ? ? yes N(5) C(16) C(15) 109.4(2) ? ? ? yes