# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_address ; ? ; _publ_contact_author_email wj10@cam.ac.uk _publ_contact_author_fax ? _publ_contact_author_phone ? _publ_contact_author_name 'William Jones' _publ_contact_letter ; ? ? ? ; _publ_requested_category ? loop_ _publ_author_name 'Mihails Arhangelskis' 'Gareth O. Lloyd' 'William Jones' data_1 _database_code_depnum_ccdc_archive 'CCDC 863387' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Fumaric acid:Pyrazine cocrystal' _chemical_melting_point ? _chemical_formula_moiety 'C4 H4 O4, C4 H4 N2 ' _chemical_formula_sum 'C8 H8 N2 O4' _chemical_formula_weight 196.16 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' 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.1006(7) _cell_length_b 6.1168(8) _cell_length_c 6.9894(10) _cell_angle_alpha 85.396(11) _cell_angle_beta 82.199(12) _cell_angle_gamma 85.176(11) _cell_volume 214.76(5) _cell_formula_units_Z 1 _cell_measurement_temperature 120 _cell_measurement_reflns_used 531 _cell_measurement_theta_min 2.9429 _cell_measurement_theta_max 30.4280 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 102 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.60239 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1627 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0680 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 28.00 _reflns_number_total 1030 _reflns_number_gt 732 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Xseed _computing_publication_material Xseed _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^)+(0.0607P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1030 _refine_ls_number_parameters 68 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0880 _refine_ls_R_factor_gt 0.0591 _refine_ls_wR_factor_ref 0.1521 _refine_ls_wR_factor_gt 0.1271 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3199(4) 0.8719(3) 0.3590(2) 0.0265(5) Uani 1 1 d . . . O2 O 0.4249(3) 0.5304(3) 0.2655(2) 0.0288(5) Uani 1 1 d . . . N1 N 0.7627(4) 0.9636(3) 0.1178(2) 0.0214(5) Uani 1 1 d . . . C2 C 0.8908(5) 0.8093(3) 0.0087(3) 0.0221(5) Uani 1 1 d . . . H2 H 0.8174 0.6713 0.0108 0.027 Uiso 1 1 calc R . . C3 C 1.1283(5) 0.8443(4) -0.1077(3) 0.0224(5) Uani 1 1 d . . . H3 H 1.2151 0.7292 -0.1818 0.027 Uiso 1 1 calc R . . C4 C 0.2786(5) 0.6611(3) 0.3571(3) 0.0209(5) Uani 1 1 d . . . H1 H 0.475(7) 0.903(5) 0.271(4) 0.065(10) Uiso 1 1 d . . . C5 C 0.0282(4) 0.6039(3) 0.4800(3) 0.0213(5) Uani 1 1 d . . . H5 H -0.0930 0.7181 0.5304 0.026 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 O1 0.0249(9) 0.0191(9) 0.0345(9) -0.0025(7) 0.0018(7) -0.0041(7) O2 0.0281(10) 0.0233(9) 0.0325(10) -0.0037(7) 0.0042(7) 0.0007(7) N1 0.0200(10) 0.0203(10) 0.0232(10) 0.0009(8) -0.0013(7) -0.0016(8) C2 0.0238(12) 0.0176(11) 0.0252(12) -0.0008(9) -0.0044(9) -0.0019(9) C3 0.0251(13) 0.0190(11) 0.0226(11) -0.0032(9) -0.0021(9) 0.0010(9) C4 0.0207(12) 0.0194(12) 0.0225(12) 0.0001(9) -0.0031(9) -0.0014(9) C5 0.0184(12) 0.0230(11) 0.0222(11) -0.0030(9) -0.0015(9) -0.0005(9) _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 O1 C4 1.326(2) . ? O1 H1 0.96(3) . ? O2 C4 1.207(2) . ? N1 C2 1.332(3) . ? N1 C3 1.335(3) 2_775 ? C2 C3 1.387(3) . ? C2 H2 0.9500 . ? C3 N1 1.335(3) 2_775 ? C3 H3 0.9500 . ? C4 C5 1.490(3) . ? C5 C5 1.326(4) 2_566 ? C5 H5 0.9500 . ? 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 C4 O1 H1 108.9(19) . . ? C2 N1 C3 116.83(19) . 2_775 ? N1 C2 C3 121.9(2) . . ? N1 C2 H2 119.1 . . ? C3 C2 H2 119.1 . . ? N1 C3 C2 121.26(19) 2_775 . ? N1 C3 H3 119.4 2_775 . ? C2 C3 H3 119.4 . . ? O2 C4 O1 124.2(2) . . ? O2 C4 C5 123.7(2) . . ? O1 C4 C5 112.07(19) . . ? C5 C5 C4 121.1(3) 2_566 . ? C5 C5 H5 119.5 2_566 . ? C4 C5 H5 119.5 . . ? 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 C3 N1 C2 C3 1.0(3) 2_775 . . . ? N1 C2 C3 N1 -1.0(4) . . . 2_775 ? O2 C4 C5 C5 10.7(4) . . . 2_566 ? O1 C4 C5 C5 -169.8(2) . . . 2_566 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.346 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.067 # Attachment '9094_web_deposit_cif_file_1_MihailsArhangelskis_1326820147.pyr_pht.cif' data_pyrphtal _database_code_depnum_ccdc_archive 'CCDC 863388' #TrackingRef '9094_web_deposit_cif_file_1_MihailsArhangelskis_1326820147.pyr_pht.cif' loop_ _audit_conform.dict_name _audit_conform.dict_version _audit_conform.dict_location cif_core.dic . ftp://ftp.iucr.org/pub/cif_core.dic cif_pd.dic . ftp://ftp.iucr.org/pub/cif_pd.dic _chemical_name_systematic ; pyrazine:phthalic acid cocrystal ; _chemical_name_common 'pyrazine:phtalic acid cocrystal' _chemical_formula_moiety 'C8 H6 O4, C4 H4 N2' _chemical_formula_structural 'C8 H6 O4, C4 H4 N2' _chemical_formula_analytical ? _chemical_formula_iupac 'C8 H6 O4, C4 H4 N2' _chemical_formula_sum 'C12 H10 N2 O4' _chemical_formula_weight 246.22 _chemical_melting_point ? _chemical_compound_source ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 '-x, -y, -z' 2 '-x, y+1/2, -z+1/2' 3 'x, -y+1/2, z+1/2' 4 'x, y, z' _cell_length_a 6.93440(24) _cell_length_b 13.59704(73) _cell_length_c 14.51054(72) _cell_angle_alpha 90 _cell_angle_beta 122.2085(29) _cell_angle_gamma 90 _cell_volume 1157.62(10) _cell_formula_units_Z 4 _cell_measurement_temperature 295 _pd_calibration_special_details ; ? ; _cell_special_details ; ? ; _exptl_crystal_density_diffrn 1.4128(1) _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 # The next three fields give the specimen dimensions in mm. The equatorial # plane contains the incident and diffracted beam. _pd_spec_size_axial 14 _pd_spec_size_equat 10 _pd_spec_size_thick 0.5 # The next five fields are character fields that describe the specimen. _pd_spec_mounting ; packed powder pellet ; _pd_spec_mount_mode reflection _pd_spec_shape flat_sheet _pd_char_particle_morphology ? _pd_char_colour white _pd_prep_cool_rate ? _pd_prep_pressure ? _pd_prep_temperature 293 # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _pd_instr_location ; ? ; _diffrn_ambient_temperature 295 _diffrn_source 'sealed X-ray tube' _diffrn_source_target Cu _diffrn_source_type ? _diffrn_measurement_device_type "Panalytical X'pert Powder" _diffrn_detector X'Celerator _diffrn_detector_type ? _pd_meas_scan_method cont _pd_meas_special_details ; ? ; # The following six items are used for angular dispersive measurements only. loop_ _diffrn_radiation_type _diffrn_radiation_wavelength CuK\a~1~ 1.54056 CuK\a~2~ 1.54439 _diffrn_radiation_monochromator none # The following four items give details of the measured (not processed) # powder pattern. Angles are in degrees. _pd_meas_number_of_points 9215 _pd_meas_2theta_range_min 3 _pd_meas_2theta_range_max 80 _pd_meas_2theta_range_inc 0.008 # The following fields are used to identify the programs used. _computing_data_collection "X'Pert Data Collector (Panalytical )" _computing_cell_refinement 'DICVOL 06 (Louer et al)' _computing_data_reduction ? _computing_structure_solution 'DASH (David et al 2008)' _computing_structure_refinement 'Topas Academic (Coelho 2007)' _computing_molecular_graphics ? _pd_proc_ls_special_details ; ? ; _pd_proc_ls_profile_function pseudo-Voigt _pd_proc_ls_background_function 'Chebyshev polynomial' _pd_proc_ls_prof_R_factor 0.092 _pd_proc_ls_prof_wR_factor 0.122 _pd_proc_ls_prof_wR_expected 0.115 _refine_special_details ; ? ; _refine_ls_structure_factor_coef Inet _refine_ls_matrix_type fullcycle _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 1/[Y~i~+\s(Y~i~)] _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_parameters 105 _refine_ls_number_restraints 61 _refine_ls_number_constraints 0 # The following item is the same as CHI, the square root of 'CHI squared' _refine_ls_goodness_of_fit_all 1.064 _refine_ls_R_I_factor .034 _refine_ls_restrained_S_all ? _refine_ls_shift/su_max ? _refine_ls_shift/su_mean ? _pd_block_diffractogram_id pyrphtalprofile # Give appropriate details in the next two text fields. _pd_proc_info_excluded_regions ? _pd_proc_info_data_reduction ? loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_B_iso_or_equiv C12 C 0.4553(19) 0.56431(44) 0.77423(53) 1 6.65(17) C11 C 0.5333(17) 0.59615(58) 0.87298(44) 1 6.65(17) C10 C 0.5731(16) 0.68962(44) 0.89275(50) 1 6.65(17) C9 C 0.5188(18) 0.75835(42) 0.80364(52) 1 6.65(17) C8 C 0.4462(12) 0.72913(39) 0.71150(62) 1 6.65(17) C13 C 0.4080(18) 0.63269(47) 0.68932(70) 1 6.65(17) C14 C 0.3272(13) 0.59283(51) 0.57734(51) 1 6.65(17) O3 O 0.3227(14) 0.64125(77) 0.49758(72) 1 6.65(17) O4 O 0.2650(11) 0.50375(59) 0.55901(47) 1 6.65(17) C7 C 0.39726(97) 0.81057(74) 0.62741(66) 1 6.65(17) O1 O 0.5353(16) 0.83994(77) 0.60752(73) 1 6.65(17) O2 O 0.17713(82) 0.83265(64) 0.56186(57) 1 6.65(17) H12 H 0.4375(53) 0.5104(35) 0.7621(23) 1 6.65(17) H11 H 0.5743(56) 0.5430(23) 0.9433(20) 1 6.65(17) H10 H 0.6308(46) 0.7193(22) 0.9747(19) 1 6.65(17) H9 H 0.5413(41) 0.8203(36) 0.8178(18) 1 6.65(17) H14 H 0.2184(44) 0.4852(26) 0.4789(24) 1 6.65(17) H13 H 0.1599(44) 0.8683(23) 0.5071(23) 1 6.65(17) N1 N -0.0425(17) 0.39850(71) 0.13755(41) 1 6.65(17) C2 C -0.0255(20) 0.49610(59) 0.16539(51) 1 6.65(17) C3 C 0.0652(20) 0.52384(58) 0.27408(48) 1 6.65(17) N4 N 0.1211(19) 0.45514(77) 0.34928(40) 1 6.65(17) C5 C 0.1009(19) 0.36136(59) 0.31934(44) 1 6.65(17) C6 C 0.0142(18) 0.33480(57) 0.21252(44) 1 6.65(17) H2 H -0.0873(49) 0.5547(22) 0.0946(22) 1 6.65(17) H3 H 0.0910(47) 0.5938(29) 0.3029(24) 1 6.65(17) H5 H 0.1595(51) 0.2979(25) 0.3929(21) 1 6.65(17) H6 H -0.0037(39) 0.2781(28) 0.1927(22) 1 6.65(17) _geom_special_details ; ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C5 N4 1.33(1) ? C5 C6 1.379(9) ? C6 N1 1.28(1) ? N1 C2 1.37(1) ? C2 C3 1.40(1) ? C14 O4 1.27(1) ? C14 O3 1.32(1) ? C14 C13 1.51(1) ? C13 C12 1.44(1) ? C11 C12 1.31(1) ? C11 C10 1.30(1) ? C10 C9 1.47(1) ? C9 C8 1.22(1) ? C8 C13 1.343(8) ? C8 C7 1.55(1) ? C7 O1 1.21(2) ? C7 O2 1.333(7) ? C6 H6 0.81(4) ? C5 H5 1.26(3) ? C3 H3 1.02(4) ? C2 H2 1.19(3) ? O4 H14 1.06(4) ? O2 H13 0.88(4) ? C12 H12 0.75(5) ? C11 H11 1.16(3) ? C10 H10 1.11(3) ? C9 H9 0.86(5) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C6 117.7(9) . . ? N1 C6 C5 122.1(9) . . ? C6 C5 N4 121.7(9) . . ? C5 N4 C3 118.2(9) . . ? N4 C3 C2 119.6(9) . . ? C3 C2 N1 120.5(9) . . ? O4 C14 O3 116.6(8) . . ? O4 C14 C13 117.3(7) . . ? C14 C13 C12 118.4(8) . . ? C13 C12 C11 119.9(8) . . ? C12 C11 C10 118.8(8) . . ? C11 C10 C9 120.1(8) . . ? C10 C9 C8 121.3(8) . . ? C9 C8 C13 119.7(8) . . ? C8 C13 C12 120.1(8) . . ? C14 C13 C8 121.4(8) . . ? C13 C8 C7 125.3(7) . . ? O2 C7 O1 120.5(9) . . ? N1 C6 H6 115(2) . . ? H5 C5 N4 117(2) . . ? N4 C3 H3 114(2) . . ? N1 C2 H2 117(2) . . ? H14 O4 C14 109(2) . . ? C13 C12 H12 120(3) . . ? H11 C11 C10 120(2) . . ? H10 C10 C9 119(2) . . ? H9 C9 C8 120(2) . . ? H13 O2 C7 109(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O4 H14 N4 . 1.06(4) 1.68(3) 2.731(9) 175(3) O2 H13 N1 2_555 0.88(4) 1.85(3) 2.68(1) 156(3) # Attachment '9095_web_deposit_cif_file_2_MihailsArhangelskis_1326820147.pyr_succ.CIF' data_2 _database_code_depnum_ccdc_archive 'CCDC 863389' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H6 O4, C4 H4 N2' _chemical_formula_sum 'C8 H10 N2 O4' _chemical_formula_weight 198.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.5311(4) _cell_length_b 5.1286(2) _cell_length_c 10.2947(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.012(5) _cell_angle_gamma 90.00 _cell_volume 438.85(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120 _cell_measurement_reflns_used 2378 _cell_measurement_theta_min 4.4044 _cell_measurement_theta_max 71.7780 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.4820 _exptl_crystal_size_mid 0.3321 _exptl_crystal_size_min 0.1818 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 208 _exptl_absorpt_coefficient_mu 1.043 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.70103 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2561 _diffrn_reflns_av_R_equivalents 0.0461 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 6.10 _diffrn_reflns_theta_max 71.92 _reflns_number_total 860 _reflns_number_gt 817 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Xseed _computing_publication_material Xseed _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^)+(0.0972P)^2^+0.1414P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 860 _refine_ls_number_parameters 65 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1368 _refine_ls_wR_factor_gt 0.1348 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.20911(12) 0.54902(19) 0.11897(10) 0.0196(3) Uani 1 1 d . . . O2 O 0.17572(12) 0.6910(2) -0.09122(10) 0.0204(3) Uani 1 1 d . . . N1 N 0.40608(14) 0.1889(2) 0.04342(12) 0.0179(4) Uani 1 1 d . . . C2 C 0.42174(17) 0.1818(3) -0.08266(15) 0.0185(4) Uani 1 1 d . . . H2 H 0.3675 0.3082 -0.1441 0.022 Uiso 1 1 calc R . . C3 C 0.51556(16) -0.0064(3) -0.12627(14) 0.0177(4) Uani 1 1 d . . . H3 H 0.5242 -0.0055 -0.2167 0.021 Uiso 1 1 calc R . . C4 C 0.14712(15) 0.7094(3) 0.01821(14) 0.0156(4) Uani 1 1 d . . . C5 C 0.03862(16) 0.9124(3) 0.05801(13) 0.0171(4) Uani 1 1 d . . . H5A H 0.1021 1.0209 0.1307 0.021 Uiso 1 1 calc R . . H5B H -0.0469 0.8241 0.0926 0.021 Uiso 1 1 calc R . . H1 H 0.2795 0.4468 0.0921 0.051(7) Uiso 1 1 d 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 O1 0.0197(6) 0.0193(6) 0.0199(6) 0.0030(4) 0.0050(4) 0.0056(4) O2 0.0197(6) 0.0223(6) 0.0189(6) -0.0007(4) 0.0035(4) 0.0031(4) N1 0.0142(6) 0.0176(7) 0.0216(7) -0.0013(4) 0.0032(5) -0.0001(4) C2 0.0157(7) 0.0182(8) 0.0200(8) 0.0011(5) 0.0010(5) 0.0001(5) C3 0.0147(7) 0.0195(7) 0.0183(7) -0.0003(5) 0.0023(5) -0.0008(5) C4 0.0114(7) 0.0145(7) 0.0195(7) -0.0009(5) 0.0007(5) -0.0022(5) C5 0.0161(7) 0.0164(7) 0.0185(7) 0.0000(5) 0.0032(5) 0.0022(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.3361(17) . ? O1 H1 0.8869 . ? O2 C4 1.2088(17) . ? N1 C2 1.3349(19) . ? N1 C3 1.3393(18) 3_655 ? C2 C3 1.391(2) . ? C2 H2 0.9500 . ? C3 N1 1.3393(18) 3_655 ? C3 H3 0.9500 . ? C4 C5 1.5098(19) . ? C5 C5 1.521(3) 3_575 ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? 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 C4 O1 H1 107.4 . . ? C2 N1 C3 117.07(12) . 3_655 ? N1 C2 C3 121.58(14) . . ? N1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? N1 C3 C2 121.35(13) 3_655 . ? N1 C3 H3 119.3 3_655 . ? C2 C3 H3 119.3 . . ? O2 C4 O1 123.22(12) . . ? O2 C4 C5 124.85(13) . . ? O1 C4 C5 111.93(12) . . ? C4 C5 C5 112.21(14) . 3_575 ? C4 C5 H5A 109.2 . . ? C5 C5 H5A 109.2 3_575 . ? C4 C5 H5B 109.2 . . ? C5 C5 H5B 109.2 3_575 . ? H5A C5 H5B 107.9 . . ? 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 C3 N1 C2 C3 -0.1(2) 3_655 . . . ? N1 C2 C3 N1 0.1(2) . . . 3_655 ? O2 C4 C5 C5 2.6(2) . . . 3_575 ? O1 C4 C5 C5 -177.29(13) . . . 3_575 ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 71.92 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.395 _refine_diff_density_min -0.403 _refine_diff_density_rms 0.088 # Attachment '9096_web_deposit_cif_file_3_MihailsArhangelskis_1326820147.pyr_ter.cif' data_pyrter _database_code_depnum_ccdc_archive 'CCDC 863390' #TrackingRef '9096_web_deposit_cif_file_3_MihailsArhangelskis_1326820147.pyr_ter.cif' loop_ _audit_conform.dict_name _audit_conform.dict_version _audit_conform.dict_location cif_core.dic . ftp://ftp.iucr.org/pub/cif_core.dic cif_pd.dic . ftp://ftp.iucr.org/pub/cif_pd.dic _chemical_name_systematic ; pyrazine:terephthalic acid cocrystal ; _chemical_name_common 'pyrazine:terephthalic acid cocrystal' _chemical_formula_moiety 'C8 H6 O4, C4 H4 N2' _chemical_formula_structural '(C8 H6 O4), (C4 H4 N2)' _chemical_formula_analytical ? _chemical_formula_iupac '(C8 H6 O4), (C4 H4 N2)' _chemical_formula_sum 'C12 H10 N2 O4' _chemical_formula_weight 246.22 _chemical_melting_point ? _chemical_compound_source ? _space_group_crystal_system triclinic _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 '-x, -y, -z' 2 'x, y, z' _cell_length_a 3.81056(10) _cell_length_b 7.07204(32) _cell_length_c 11.50344(44) _cell_angle_alpha 94.9505(15) _cell_angle_beta 93.5324(20) _cell_angle_gamma 115.2753(18) _cell_volume 277.604(19) _cell_formula_units_Z 1 _cell_measurement_temperature 295 _pd_calibration_special_details ; ? ; _cell_special_details ; ? ; _exptl_crystal_density_diffrn 1.4728(1) _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 128 # The next three fields give the specimen dimensions in mm. The equatorial # plane contains the incident and diffracted beam. _pd_spec_size_axial 14 _pd_spec_size_equat 10 _pd_spec_size_thick 0.5 # The next five fields are character fields that describe the specimen. _pd_spec_mounting ; packed powder pellet ; _pd_spec_mount_mode reflection _pd_spec_shape flat_sheet _pd_char_particle_morphology ? _pd_char_colour white _pd_prep_cool_rate ? _pd_prep_pressure ? _pd_prep_temperature 293 # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; # This 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 ; ? ; _diffrn_ambient_temperature 295 _diffrn_source 'sealed X-ray tube' _diffrn_source_target Cu _diffrn_source_type ? _diffrn_measurement_device_type "Panalytical X'pert Powder" _diffrn_detector X'Celerator _diffrn_detector_type ? _pd_meas_scan_method cont _pd_meas_special_details ; ? ; # The following six items are used for angular dispersive measurements only. loop_ _diffrn_radiation_type _diffrn_radiation_wavelength CuK\a~1~ 1.54056 CuK\a~2~ 1.54439 _diffrn_radiation_monochromator none # The following four items give details of the measured (not processed) # powder pattern. Angles are in degrees. _pd_meas_number_of_points 36861 _pd_meas_2theta_range_min 3 _pd_meas_2theta_range_max 80 _pd_meas_2theta_range_inc 0.002 # The following fields are used to identify the programs used. _computing_data_collection "X'Pert Data Collector (Panalytical)" _computing_cell_refinement 'DICVOL 06 (Louer et al)' _computing_data_reduction ? _computing_structure_solution 'DASH (David et al 2008)' _computing_structure_refinement 'Topas Academic (Coelho 2007)' _computing_molecular_graphics ? # 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 pseudo-Voigt _pd_proc_ls_background_function 'Chebyshev polynomial' _pd_proc_ls_pref_orient_corr ; ? ; _pd_proc_ls_prof_R_factor 0.045 _pd_proc_ls_prof_wR_factor 0.058 _pd_proc_ls_prof_wR_expected 0.024 _refine_special_details ; ? ; _refine_ls_structure_factor_coef Inet _refine_ls_matrix_type fullcycle _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 1/[Y~i~+\s(Y~i~)] _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_parameters 41 _refine_ls_number_restraints 6 _refine_ls_number_constraints 31 # The following item is the same as CHI, the square root of 'CHI squared' _refine_ls_goodness_of_fit_all 2.445 _refine_ls_R_I_factor .016 _refine_ls_restrained_S_all ? _refine_ls_shift/su_max ? _refine_ls_shift/su_mean ? # Each refinement must be accompanied by a listing of the powder data # in CIF format. Each listing should be sent as a separate file consisting # of one data block containing a single powder profile. The value of # _pd_block_diffractogram_id is used to associate each refinement with # its corresponding powder profile, since it must match the value # of _pd_block_id in the file containing the powder data. _pd_block_diffractogram_id pyrterprofile # Give appropriate details in the next two text fields. _pd_proc_info_excluded_regions ? _pd_proc_info_data_reduction ? loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_B_iso_or_equiv C2 C 0.6140602 0.7120313 0.4997557 1 5.377(56) C3 C 0.3941744 0.5734931 0.4008305 1 5.377(56) C4 C 0.2674373 0.3569585 0.4006447 1 5.377(56) C1 C 0.2950161 0.6565216 0.2957208 1 5.377(56) O1 O 0.416321 0.8669972 0.3029773 1 5.377(56) O2 O 0.1123083 0.541106 0.2064061 1 5.377(56) H1 H 0.3562371 0.9271059 0.23835 1 5.377(56) H2 H 0.7003686 0.8594921 0.4998823 1 5.377(56) H4 H 0.1176943 0.2626136 0.3332762 1 5.377(56) N1 N 0.142323 0.960415 0.1036339 1 5.377(56) C5 C -0.1413442 0.8044174 0.02840687 1 5.377(56) C6 C 0.2656347 1.162534 0.08115812 1 5.377(56) H5 H -0.2309182 0.6619199 0.04295755 1 5.377(56) H6 H 0.4642874 1.273658 0.1330678 1 5.377(56) #_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 O2 C1 1.2200 . . ? O1 C1 1.3500 . . ? C1 C3 1.4850 . . ? C3 C4 1.3950 . . ? C2 C3 1.3950 . . ? C2 C4 1.405(3) . 1_666 ? N1 C6 1.3550 . . ? N1 C5 1.3550 . . ? C5 C6 1.393(3) . 1_575 ? C2 H2 0.9500 . . ? C4 H4 0.9500 . . ? O1 H1 0.9500 . . ? C5 H5 0.9500 . . ? C6 H6 0.9500 . . ? 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 O1 C1 O2 121.00 . . ? O2 C1 C3 122.00 . . ? O1 C1 C3 117.00 . . ? C1 C3 C2 120.00 . . ? C1 C3 C4 120.00 . . ? C2 C3 C4 120.00 . . ? C3 C2 C4 122.38 . 1_666 ? C3 C4 C2 117.54 . 1_666 ? C5 N1 C6 119.00 . . ? N1 C5 C6 122.64 . 1_575 ? N1 C6 C5 117.43 . 1_575 ? H1 O1 C1 120.00 . . ? H2 C2 C3 120.00 . . ? H4 C4 C3 120.00 . . ? H6 C6 N1 120.00 . . ? H5 C5 N1 120.00 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O1 H1 N1 . 0.9500 1.787 2.709 162.92