# 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 _publ_contact_author_name 'Grepioni, Fabrizia' _publ_contact_author_email gil21@cam.ac.uk _publ_section_title ; Structure determination of novel ionic co-crystals from powder data: the use of rigid fragments in simulated annealing algorithms ; loop_ _publ_author_name F.Grepioni D.Braga G.Lampronti # Attachment '- BA_CaI2_(H2O)5.cif' data_cai2barb(h2o)5 _database_code_depnum_ccdc_archive 'CCDC 863196' #TrackingRef '- BA_CaI2_(H2O)5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H14 Ca I2 N2 O8' _chemical_formula_weight 512.05 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' Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 10.1868(4) _cell_length_b 14.2071(5) _cell_length_c 11.0417(5) _cell_angle_alpha 90.00 _cell_angle_beta 107.926(5) _cell_angle_gamma 90.00 _cell_volume 1520.43(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 2.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 4.5 _exptl_absorpt_correction_T_min 0.94764 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 16.1340 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6596 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0587 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 28.95 _reflns_number_total 3420 _reflns_number_gt 2115 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(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^)+(0.0193P)^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 SHELXL _refine_ls_extinction_coef 0.00420(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3420 _refine_ls_number_parameters 203 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0521 _refine_ls_wR_factor_gt 0.0482 _refine_ls_goodness_of_fit_ref 0.834 _refine_ls_restrained_S_all 0.851 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 1.33779(3) 0.584614(19) 0.58664(3) 0.03885(10) Uani 1 1 d . . . I2 I 1.25888(3) 0.91665(2) 0.49449(3) 0.04504(11) Uani 1 1 d . . . Ca1 Ca 0.88307(9) 0.74734(5) 0.64702(8) 0.0269(2) Uani 1 1 d . . . OW1 O 1.1309(4) 0.7576(2) 0.6795(4) 0.0466(9) Uani 1 1 d D . . OW2 O 0.9547(4) 0.7523(3) 0.8758(3) 0.0493(9) Uani 1 1 d D . . OW3 O 0.9538(5) 0.9104(2) 0.6931(4) 0.0663(11) Uani 1 1 d D . . OW4 O 0.7635(5) 0.8287(3) 0.4542(4) 0.0615(11) Uani 1 1 d D . . OW5 O 0.7004(4) 0.6314(2) 0.5964(4) 0.0513(10) Uani 1 1 d D . . H200 H 0.928(6) 0.706(3) 0.910(5) 0.09(2) Uiso 1 1 d D . . H500 H 0.708(6) 0.590(3) 0.545(4) 0.09(2) Uiso 1 1 d D . . H501 H 0.640(5) 0.627(4) 0.633(6) 0.10(2) Uiso 1 1 d D . . H201 H 0.932(5) 0.792(3) 0.922(4) 0.058(18) Uiso 1 1 d D . . H101 H 1.158(5) 0.803(2) 0.645(4) 0.056(17) Uiso 1 1 d D . . H100 H 1.165(9) 0.710(4) 0.655(8) 0.19(4) Uiso 1 1 d D . . H401 H 0.727(6) 0.882(2) 0.457(6) 0.08(2) Uiso 1 1 d D . . H400 H 0.687(5) 0.815(6) 0.402(7) 0.19(4) Uiso 1 1 d D . . H300 H 0.901(8) 0.959(5) 0.638(8) 0.28(6) Uiso 1 1 d D . . H301 H 1.023(4) 0.938(4) 0.740(6) 0.13(3) Uiso 1 1 d D . . O2 O 0.9942(3) 0.59245(17) 0.7420(3) 0.0419(8) Uani 1 1 d . . . C2 C 0.9842(4) 0.5082(3) 0.7222(4) 0.0258(10) Uani 1 1 d . . . N3 N 1.0523(4) 0.4647(2) 0.6487(3) 0.0290(9) Uani 1 1 d . . . N1 N 0.8997(4) 0.4522(2) 0.7687(4) 0.0333(9) Uani 1 1 d . . . C6 C 0.8881(5) 0.3562(3) 0.7544(4) 0.0353(11) Uani 1 1 d . . . O4 O 1.0906(3) 0.3447(2) 0.5343(3) 0.0486(9) Uani 1 1 d . . . C4 C 1.0402(4) 0.3716(3) 0.6128(4) 0.0291(10) Uani 1 1 d . . . C5 C 0.9683(5) 0.3105(3) 0.6802(4) 0.0309(11) Uani 1 1 d . . . H5A H 0.9062 0.2699 0.6176 0.037 Uiso 1 1 calc R . . H5B H 1.0368 0.2703 0.7375 0.037 Uiso 1 1 calc R . . O6 O 0.8167(4) 0.3121(2) 0.8031(4) 0.0592(10) Uani 1 1 d . . . H1 H 0.873(5) 0.484(3) 0.832(4) 0.050(14) Uiso 1 1 d . . . H2 H 1.115(5) 0.502(3) 0.620(4) 0.057(15) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.03256(17) 0.03624(17) 0.0505(2) 0.00226(15) 0.01678(15) -0.00078(16) I2 0.0545(2) 0.03616(17) 0.0462(2) 0.00553(16) 0.01802(17) -0.00230(18) Ca1 0.0292(5) 0.0252(4) 0.0294(5) -0.0035(4) 0.0134(4) 0.0003(4) OW1 0.043(2) 0.0386(19) 0.069(3) 0.0038(19) 0.0319(19) -0.007(2) OW2 0.067(3) 0.049(2) 0.038(2) -0.0018(19) 0.0240(19) 0.009(2) OW3 0.067(3) 0.0350(18) 0.077(3) -0.004(2) -0.008(2) -0.007(2) OW4 0.083(3) 0.043(2) 0.043(2) 0.0000(17) -0.003(2) 0.015(2) OW5 0.047(2) 0.0400(19) 0.084(3) -0.0197(19) 0.044(2) -0.0095(18) O2 0.058(2) 0.0207(16) 0.052(2) -0.0026(14) 0.0234(17) -0.0008(16) C2 0.025(3) 0.027(2) 0.025(3) 0.0031(18) 0.007(2) 0.0025(19) N3 0.038(2) 0.0277(19) 0.029(2) -0.0010(16) 0.0206(19) -0.0075(19) N1 0.036(2) 0.0320(19) 0.039(3) -0.0028(17) 0.022(2) 0.0008(19) C6 0.030(3) 0.038(3) 0.039(3) 0.007(2) 0.012(2) -0.004(2) O4 0.059(2) 0.0508(18) 0.048(2) -0.0117(16) 0.035(2) 0.0065(18) C4 0.026(3) 0.034(2) 0.026(3) 0.0041(19) 0.005(2) 0.005(2) C5 0.032(3) 0.021(2) 0.038(3) -0.0004(18) 0.009(2) -0.003(2) O6 0.052(2) 0.066(2) 0.072(3) 0.0196(19) 0.037(2) -0.018(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Ca1 OW4 2.399(4) . ? Ca1 OW2 2.405(4) . ? Ca1 OW5 2.419(4) . ? Ca1 OW3 2.433(4) . ? Ca1 OW1 2.442(3) . ? Ca1 O6 2.446(3) 2_656 ? Ca1 O4 2.474(3) 3_766 ? Ca1 O2 2.548(3) . ? OW1 H101 0.838(19) . ? OW1 H100 0.85(2) . ? OW2 H200 0.85(2) . ? OW2 H201 0.843(19) . ? OW3 H300 0.960(18) . ? OW3 H301 0.83(2) . ? OW4 H401 0.851(19) . ? OW4 H400 0.84(2) . ? OW5 H500 0.831(19) . ? OW5 H501 0.84(2) . ? O2 C2 1.216(4) . ? C2 N3 1.366(5) . ? C2 N1 1.382(5) . ? N3 C4 1.375(5) . ? N3 H2 0.96(4) . ? N1 C6 1.373(5) . ? N1 H1 0.95(4) . ? C6 O6 1.205(5) . ? C6 C5 1.474(6) . ? O4 C4 1.199(5) . ? O4 Ca1 2.474(3) 3_766 ? C4 C5 1.476(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? O6 Ca1 2.446(3) 2_646 ? 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 OW4 Ca1 OW2 145.59(13) . . ? OW4 Ca1 OW5 88.78(16) . . ? OW2 Ca1 OW5 103.03(14) . . ? OW4 Ca1 OW3 76.32(14) . . ? OW2 Ca1 OW3 77.18(14) . . ? OW5 Ca1 OW3 148.66(14) . . ? OW4 Ca1 OW1 108.75(15) . . ? OW2 Ca1 OW1 83.01(13) . . ? OW5 Ca1 OW1 139.60(12) . . ? OW3 Ca1 OW1 71.74(14) . . ? OW4 Ca1 O6 77.78(14) . 2_656 ? OW2 Ca1 O6 75.92(13) . 2_656 ? OW5 Ca1 O6 70.95(12) . 2_656 ? OW3 Ca1 O6 78.94(14) . 2_656 ? OW1 Ca1 O6 147.00(13) . 2_656 ? OW4 Ca1 O4 71.85(12) . 3_766 ? OW2 Ca1 O4 142.37(12) . 3_766 ? OW5 Ca1 O4 73.75(12) . 3_766 ? OW3 Ca1 O4 125.02(13) . 3_766 ? OW1 Ca1 O4 77.65(12) . 3_766 ? O6 Ca1 O4 133.31(12) 2_656 3_766 ? OW4 Ca1 O2 145.20(12) . . ? OW2 Ca1 O2 68.92(11) . . ? OW5 Ca1 O2 73.71(12) . . ? OW3 Ca1 O2 132.14(13) . . ? OW1 Ca1 O2 71.50(11) . . ? O6 Ca1 O2 121.81(11) 2_656 . ? O4 Ca1 O2 74.41(10) 3_766 . ? Ca1 OW1 H101 117(3) . . ? Ca1 OW1 H100 114(6) . . ? H101 OW1 H100 104(6) . . ? Ca1 OW2 H200 114(4) . . ? Ca1 OW2 H201 127(3) . . ? H200 OW2 H201 94(5) . . ? Ca1 OW3 H300 118(5) . . ? Ca1 OW3 H301 135(5) . . ? H300 OW3 H301 105(4) . . ? Ca1 OW4 H401 121(4) . . ? Ca1 OW4 H400 128(7) . . ? H401 OW4 H400 84(7) . . ? Ca1 OW5 H500 114(4) . . ? Ca1 OW5 H501 125(4) . . ? H500 OW5 H501 120(6) . . ? C2 O2 Ca1 140.8(3) . . ? O2 C2 N3 121.5(4) . . ? O2 C2 N1 121.8(4) . . ? N3 C2 N1 116.6(4) . . ? C2 N3 C4 126.1(4) . . ? C2 N3 H2 117(3) . . ? C4 N3 H2 117(3) . . ? C6 N1 C2 124.8(4) . . ? C6 N1 H1 122(3) . . ? C2 N1 H1 111(3) . . ? O6 C6 N1 120.5(4) . . ? O6 C6 C5 122.2(4) . . ? N1 C6 C5 117.3(4) . . ? C4 O4 Ca1 158.6(3) . 3_766 ? O4 C4 N3 119.6(4) . . ? O4 C4 C5 124.5(4) . . ? N3 C4 C5 115.8(4) . . ? C6 C5 C4 117.8(3) . . ? C6 C5 H5A 107.9 . . ? C4 C5 H5A 107.9 . . ? C6 C5 H5B 107.9 . . ? C4 C5 H5B 107.9 . . ? H5A C5 H5B 107.2 . . ? C6 O6 Ca1 162.7(3) . 2_646 ? _diffrn_measured_fraction_theta_max 0.851 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.654 _refine_diff_density_min -0.813 _refine_diff_density_rms 0.105 # Attachment '- oxamide_CaCl2_(H2O)2.cif' data_ _database_code_depnum_ccdc_archive 'CCDC 869431' _chemical_name_mineral ?? _cell_length_a 7.5824(11) _cell_length_b 17.7713(25) _cell_length_c 6.41769(85) _cell_angle_alpha 90 _cell_angle_beta 91.1585(44) _cell_angle_gamma 90 _cell_volume 864.60(21) _symmetry_space_group_name_H-M P121/a1 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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_symmetry_multiplicity _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_B_iso_or_equiv Cl1 Cl 0 -0.5162(20) 0.61608(56) -0.7363(27) 1 6.869245 Cl2 Cl 0 -0.0204(22) 0.59237(40) 0.2645(24) 1 6.158633 CA1 Ca 0 0.50026(63) 0.44624(28) 0.24070(88) 1 4.895324 OW2 O 0 0.28991(65) 0.51173(38) 0.4185(10) 1 7.74(38) OW1 O 0 0.6971(47) 0.5046(17) 0.0319(51) 1 7.74(38) C1 C 0 0.26175(29) 0.722290(90) -0.30626(25) 1 7.74(38) N1 N 0 0.27171(21) 0.75982(13) -0.48468(29) 1 7.74(38) O1 O 0 0.29584(16) 0.656610(86) -0.27229(39) 1 7.74(38) C2 C 0 0.19117(27) 0.77371(10) -0.12200(19) 1 7.74(38) N2 N 0 0.16407(18) 0.73490(13) 0.04787(28) 1 7.74(38) O2 O 0 0.17234(16) 0.840960(96) -0.15490(34) 1 7.74(38)