Supplementary information for CrystEngComm This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Iain Oswald' 'C R Pulham' _publ_contact_author_name 'Iain Oswald' _publ_contact_author_email IAIN.OSWALD@ED.AC.UK _publ_section_title ; Co-crystallisation at high pressure - an additional tool for the preparation and study of co-crystals ; # Attachment 'CompoundI.cif' data_CompoundI _database_code_depnum_ccdc_archive 'CCDC 683518' _audit_creation_date 08-02-26 _audit_creation_method CRYSTALS_ver_12.85 _oxford_structure_analysis_title 'Parpip in P-1' _chemical_name_systematic '2:1:2 Paracetamol:piperazine:ethanol solvate' _chemical_melting_point ? #looking for refcif # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ _cell_length_a 7.544(5) _cell_length_b 8.604(7) _cell_length_c 10.394(3) _cell_angle_alpha 93.18(5) _cell_angle_beta 97.73(4) _cell_angle_gamma 114.70(5) _cell_volume 602.7(7) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C12 H17 N3 O2 # Dc = 1.30 Fooo = 260.00 Mu = 0.90 M = 235.29 # Found Formula = C12 H20 N2 O3 # Dc = 1.32 FOOO = 260.00 Mu = 0.95 M = 240.30 _chemical_formula_sum 'C12 H20 N2 O3' _chemical_formula_moiety 'C8 H9 N O2, 0.5(C4 H10 N2), C2 H6 O' _chemical_compound_source ? _chemical_formula_weight 240.30 _cell_measurement_reflns_used 471 _cell_measurement_theta_min 3 _cell_measurement_theta_max 19 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.10 _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 260 _exptl_absorpt_coefficient_mu 0.095 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.33 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device 'Bruker SMART APEX II' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 293 _diffrn_ambient_pressure 570000 _diffrn_reflns_number 14105 _reflns_number_total 1043 _diffrn_reflns_av_R_equivalents 0.0934 # Number of reflections with Friedels Law is 1043 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1752 _diffrn_reflns_theta_min 2.626 _diffrn_reflns_theta_max 23.354 _diffrn_measured_fraction_theta_max 0.591 _diffrn_reflns_theta_full 17.983 _diffrn_measured_fraction_theta_full 0.659 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _reflns_limit_h_min -8 _reflns_limit_h_max 7 _reflns_limit_k_min -6 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 11 _oxford_diffrn_Wilson_B_factor 3.31 _oxford_diffrn_Wilson_scale 0.12 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.27 _refine_diff_density_max 0.31 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 1039 _refine_ls_number_restraints 130 _refine_ls_number_parameters 154 _oxford_refine_ls_R_factor_ref 0.1123 _refine_ls_wR_factor_ref 0.2084 _refine_ls_goodness_of_fit_ref 0.9272 _refine_ls_shift/su_max 0.000061 # The values computed from all data _oxford_reflns_number_all 1039 _refine_ls_R_factor_all 0.1123 _refine_ls_wR_factor_all 0.2084 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 609 _refine_ls_R_factor_gt 0.0604 _refine_ls_wR_factor_gt 0.1659 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.15P)^2^ + 0.00P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens O3 O 0.2890(6) 0.2677(6) 0.7748(4) 0.0703 1.0000 Uani . U . . . . . C11 C 0.3258(9) 0.1206(11) 0.7340(7) 0.0638 1.0000 Uani . U . . . . . C12 C 0.3179(8) 0.0062(10) 0.8324(6) 0.0630 1.0000 Uani . U . . . . . H3 H 0.1931 0.2027 0.8091 0.1093 1.0000 Uiso R . . . . . . H121 H 0.3430 -0.0864 0.8017 0.0850 1.0000 Uiso R . . . . . . H122 H 0.4132 0.0713 0.9075 0.0850 1.0000 Uiso R . . . . . . H123 H 0.1887 -0.0379 0.8562 0.0850 1.0000 Uiso R . . . . . . H111 H 0.4539 0.1630 0.7108 0.0829 1.0000 Uiso R . . . . . . H112 H 0.2291 0.0555 0.6596 0.0829 1.0000 Uiso R . . . . . . O1 O 0.9388(4) 1.1401(5) 0.8670(3) 0.0521 1.0000 Uani . U . . . . . C1 C 0.7941(6) 0.9890(10) 0.7973(5) 0.0439 1.0000 Uani . U . . . . . C2 C 0.7398(7) 0.8414(9) 0.8500(5) 0.0451 1.0000 Uani . U . . . . . C3 C 0.5915(6) 0.6873(9) 0.7827(5) 0.0440 1.0000 Uani . U . . . . . C4 C 0.4926(7) 0.6891(9) 0.6592(5) 0.0407 1.0000 Uani . U . . . . . C5 C 0.5477(7) 0.8388(9) 0.6053(5) 0.0431 1.0000 Uani . U . . . . . C6 C 0.6983(7) 0.9915(9) 0.6729(5) 0.0477 1.0000 Uani . U . . . . . C7 C 0.2282(7) 0.4892(10) 0.4779(5) 0.0502 1.0000 Uani . U . . . . . C8 C 0.0752(7) 0.3028(8) 0.4460(6) 0.0535 1.0000 Uani . U . . . . . O2 O 0.2539(5) 0.5873(7) 0.4001(4) 0.0614 1.0000 Uani . U . . . . . N1 N 0.3390(5) 0.5257(7) 0.6000(4) 0.0467 1.0000 Uani . U . . . . . H21 H 0.8043 0.8467 0.9406 0.0590 1.0000 Uiso R . . . . . . H31 H 0.5615 0.5790 0.8224 0.0586 1.0000 Uiso R . . . . . . H51 H 0.4884 0.8417 0.5191 0.0579 1.0000 Uiso R . . . . . . H61 H 0.7389 1.0989 0.6337 0.0592 1.0000 Uiso R . . . . . . H81 H 0.0787 0.2372 0.5185 0.0845 1.0000 Uiso R . . . . . . H82 H 0.0982 0.2500 0.3701 0.0852 1.0000 Uiso R . . . . . . H83 H -0.0556 0.2985 0.4247 0.0854 1.0000 Uiso R . . . . . . H10 H 0.9114 1.2318 0.8828 0.0738 1.0000 Uiso R . . . . . . H11 H 0.3263 0.4400 0.6464 0.0500 1.0000 Uiso R . . . . . . N2 N 0.1242(5) 0.5894(6) 0.1211(4) 0.0538 1.0000 Uani . U . . . . . C9 C 0.2081(7) 0.5674(9) 0.0039(5) 0.0571 1.0000 Uani . U . . . . . C10 C -0.0690(7) 0.4394(9) 0.1175(5) 0.0541 1.0000 Uani . U . . . . . H91 H 0.2242 0.4537 -0.0010 0.0710 1.0000 Uiso R . . . . . . H92 H 0.3445 0.6554 0.0069 0.0703 1.0000 Uiso R . . . . . . H101 H -0.0464 0.3330 0.1090 0.0700 1.0000 Uiso R . . . . . . H102 H -0.1177 0.4451 0.1982 0.0695 1.0000 Uiso R . . . . . . H2 H 0.1972 0.5627 0.1871 0.0634 1.0000 Uiso 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 O3 0.071(2) 0.044(3) 0.089(3) 0.007(3) 0.029(2) 0.015(2) C11 0.062(4) 0.055(5) 0.072(4) 0.003(3) 0.023(3) 0.019(3) C12 0.065(4) 0.047(5) 0.074(4) -0.001(3) 0.019(3) 0.021(3) O1 0.0483(19) 0.037(3) 0.058(2) -0.013(3) -0.0030(16) 0.0119(19) C1 0.029(2) 0.041(3) 0.052(3) -0.006(2) 0.0041(18) 0.008(2) C2 0.041(3) 0.046(3) 0.046(3) -0.003(2) 0.002(2) 0.018(3) C3 0.046(3) 0.039(4) 0.046(2) 0.002(3) 0.0044(19) 0.019(2) C4 0.038(2) 0.038(3) 0.041(2) -0.002(2) 0.0067(18) 0.012(2) C5 0.040(3) 0.044(3) 0.039(3) 0.002(2) 0.002(2) 0.015(3) C6 0.046(3) 0.041(4) 0.047(2) 0.000(3) 0.0083(19) 0.011(2) C7 0.043(3) 0.051(4) 0.043(2) -0.009(2) 0.010(2) 0.008(3) C8 0.041(3) 0.051(4) 0.056(3) -0.011(3) 0.000(2) 0.012(3) O2 0.068(2) 0.059(4) 0.045(2) -0.005(2) 0.002(2) 0.019(3) N1 0.045(2) 0.037(3) 0.047(2) -0.004(2) 0.0051(16) 0.008(2) N2 0.054(2) 0.047(4) 0.048(2) -0.011(3) -0.0036(18) 0.016(2) C9 0.047(3) 0.056(5) 0.058(2) -0.007(4) 0.0012(19) 0.017(3) C10 0.063(3) 0.045(5) 0.049(3) 0.002(4) 0.010(2) 0.019(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 3.03(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O3 . C11 . 1.458(11) yes O3 . H3 . 0.847 no C11 . C12 . 1.448(13) yes C11 . H111 . 0.950 no C11 . H112 . 0.950 no C12 . H121 . 0.942 no C12 . H122 . 0.950 no C12 . H123 . 0.960 no O1 . C1 . 1.380(6) yes O1 . H10 . 0.908 no C1 . C2 . 1.336(10) yes C1 . C6 . 1.400(9) yes C2 . C3 . 1.395(7) yes C2 . H21 . 0.989 no C3 . C4 . 1.399(9) yes C3 . H31 . 0.991 no C4 . C5 . 1.358(10) yes C4 . N1 . 1.431(7) yes C5 . C6 . 1.395(7) yes C5 . H51 . 0.953 no C6 . H61 . 0.976 no C7 . C8 . 1.518(9) yes C7 . O2 . 1.177(9) yes C7 . N1 . 1.364(7) yes C8 . H81 . 0.970 no C8 . H82 . 0.960 no C8 . H83 . 0.967 no N1 . H11 . 0.882 no N2 . C9 . 1.484(5) yes N2 . C10 . 1.483(6) yes N2 . H2 . 0.921 no C9 . C10 2_565 1.510(9) yes C9 . H91 . 1.034 no C9 . H92 . 0.986 no C10 . H101 . 1.000 no C10 . H102 . 0.967 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C11 . O3 . H3 . 90.2 no O3 . C11 . C12 . 114.8(6) yes O3 . C11 . H111 . 108.2 no C12 . C11 . H111 . 108.0 no O3 . C11 . H112 . 108.2 no C12 . C11 . H112 . 108.0 no H111 . C11 . H112 . 109.5 no C11 . C12 . H121 . 111.6 no C11 . C12 . H122 . 108.3 no H121 . C12 . H122 . 110.2 no C11 . C12 . H123 . 108.7 no H121 . C12 . H123 . 109.3 no H122 . C12 . H123 . 108.7 no C1 . O1 . H10 . 119.9 no O1 . C1 . C2 . 120.3(6) yes O1 . C1 . C6 . 119.9(7) yes C2 . C1 . C6 . 119.8(5) yes C1 . C2 . C3 . 121.4(6) yes C1 . C2 . H21 . 117.3 no C3 . C2 . H21 . 121.2 no C2 . C3 . C4 . 119.1(7) yes C2 . C3 . H31 . 119.2 no C4 . C3 . H31 . 121.7 no C3 . C4 . C5 . 119.5(5) yes C3 . C4 . N1 . 114.8(7) yes C5 . C4 . N1 . 125.6(5) yes C4 . C5 . C6 . 120.7(6) yes C4 . C5 . H51 . 121.0 no C6 . C5 . H51 . 118.2 no C1 . C6 . C5 . 119.3(7) yes C1 . C6 . H61 . 120.0 no C5 . C6 . H61 . 120.7 no C8 . C7 . O2 . 122.0(5) yes C8 . C7 . N1 . 113.4(7) yes O2 . C7 . N1 . 124.4(5) yes C7 . C8 . H81 . 111.8 no C7 . C8 . H82 . 109.8 no H81 . C8 . H82 . 109.3 no C7 . C8 . H83 . 109.6 no H81 . C8 . H83 . 109.3 no H82 . C8 . H83 . 106.9 no C4 . N1 . C7 . 126.9(6) yes C4 . N1 . H11 . 114.1 no C7 . N1 . H11 . 118.6 no C9 . N2 . C10 . 109.4(4) yes C9 . N2 . H2 . 103.4 no C10 . N2 . H2 . 98.0 no C10 2_565 C9 . N2 . 109.1(4) yes C10 2_565 C9 . H91 . 108.2 no N2 . C9 . H91 . 111.0 no C10 2_565 C9 . H92 . 112.7 no N2 . C9 . H92 . 112.9 no H91 . C9 . H92 . 102.8 no C9 2_565 C10 . N2 . 108.4(6) yes C9 2_565 C10 . H101 . 107.7 no N2 . C10 . H101 . 107.5 no C9 2_565 C10 . H102 . 114.3 no N2 . C10 . H102 . 110.2 no H101 . C10 . H102 . 108.5 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag O3 . H3 . O1 1_445 153 0.85 1.95 2.735(9) yes C2 . H21 . O1 2_777 161 0.99 2.55 3.502(9) yes C3 . H31 . O3 . 136 0.99 2.57 3.358(9) yes O1 . H10 . N2 2_676 167 0.91 1.67 2.563(9) yes O1 . H10 . C9 2_676 160 0.91 2.56 3.424(9) yes O1 . H10 . C10 2_676 140 0.91 2.57 3.317(9) yes N1 . H11 . O3 . 171 0.88 2.01 2.881(9) yes N2 . H2 . O2 . 139 0.92 2.18 2.937(9) yes