# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Sally Price' _publ_contact_author_email S.L.PRICE@UCL.AC.UK _publ_section_title ; The crystal structures of chloro and methyl ortho-benzoic acids and their co-crystal: rationalizing similarities and differences ; loop_ _publ_author_name 'Sally Price' 'Dario Braga' "Emiliana D'Oria" 'Fabrizia Grepioni' 'Panagiotis G Karamertzanis' 'Lucia Maini' ; M.Polito ; #===END data_o-clbz-150k _database_code_depnum_ccdc_archive 'CCDC 694059' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H5 Cl O2' _chemical_formula_weight 156.56 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.6382(16) _cell_length_b 3.8142(6) _cell_length_c 23.812(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.146(11) _cell_angle_gamma 90.00 _cell_volume 1304.4(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1724 _cell_measurement_theta_min 2.6110 _cell_measurement_theta_max 28.7440 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.594 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.500 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.91630 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2978 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1146 _reflns_number_gt 955 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 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^)+(0.0813P)^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 0.0071(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1146 _refine_ls_number_parameters 96 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1185 _refine_ls_wR_factor_gt 0.1116 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.994 _refine_ls_shift/su_max 0.091 _refine_ls_shift/su_mean 0.012 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 Cl1 Cl 0.10159(5) 0.0735(2) 0.67822(3) 0.0286(3) Uani 1 1 d . . . C1 C 0.19782(17) 0.3210(7) 0.59733(10) 0.0184(6) Uani 1 1 d . . . C2 C 0.20105(18) 0.1699(7) 0.65103(11) 0.0200(6) Uani 1 1 d . . . C3 C 0.28529(18) 0.0915(8) 0.68615(11) 0.0237(7) Uani 1 1 d . . . H3 H 0.2866 -0.0083 0.7219 0.028 Uiso 1 1 calc R . . C4 C 0.36759(19) 0.1616(8) 0.66805(11) 0.0269(7) Uani 1 1 d . . . H4 H 0.4241 0.1058 0.6916 0.032 Uiso 1 1 calc R . . C5 C 0.36650(18) 0.3143(8) 0.61518(11) 0.0256(7) Uani 1 1 d . . . H5 H 0.4219 0.3633 0.6032 0.031 Uiso 1 1 calc R . . C6 C 0.28215(18) 0.3928(7) 0.58055(11) 0.0214(6) Uani 1 1 d . . . H6 H 0.2814 0.4962 0.5451 0.026 Uiso 1 1 calc R . . C7 C 0.10958(18) 0.4012(7) 0.55617(11) 0.0205(6) Uani 1 1 d . . . O1 O 0.12209(14) 0.6027(6) 0.51375(8) 0.0288(6) Uani 1 1 d . . . H100 H 0.073(3) 0.622(11) 0.4924(16) 0.067(14) Uiso 1 1 d . . . O2 O 0.03352(12) 0.2844(6) 0.56032(7) 0.0314(6) Uani 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 Cl1 0.0200(4) 0.0444(5) 0.0205(4) 0.0071(3) 0.0017(3) -0.0053(3) O1 0.0177(11) 0.0456(14) 0.0203(10) 0.0121(9) -0.0034(9) -0.0038(9) O2 0.0172(11) 0.0495(14) 0.0250(11) 0.0134(10) -0.0020(8) -0.0035(10) C6 0.0219(14) 0.0244(15) 0.0172(14) -0.0006(11) 0.0024(11) -0.0020(12) C3 0.0230(14) 0.0292(16) 0.0162(13) 0.0028(11) -0.0032(11) -0.0008(12) C1 0.0180(14) 0.0211(14) 0.0150(13) -0.0026(11) 0.0005(10) -0.0005(11) C2 0.0172(13) 0.0208(14) 0.0214(13) -0.0026(11) 0.0023(10) -0.0011(11) C7 0.0187(14) 0.0257(16) 0.0164(13) -0.0011(11) 0.0016(11) 0.0003(12) C5 0.0168(14) 0.0343(17) 0.0255(15) -0.0052(13) 0.0034(11) -0.0013(12) C4 0.0191(14) 0.0318(17) 0.0253(15) -0.0027(13) -0.0064(11) 0.0030(13) _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 1.743(3) . ? O1 C7 1.310(3) . ? O2 C7 1.221(3) . ? C6 C5 1.379(4) . ? C6 C1 1.396(4) . ? C3 C4 1.382(4) . ? C3 C2 1.382(4) . ? C1 C2 1.395(4) . ? C1 C7 1.494(3) . ? C5 C4 1.384(4) . ? 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 C5 C6 C1 121.7(2) . . ? C4 C3 C2 119.9(2) . . ? C2 C1 C6 117.9(2) . . ? C2 C1 C7 123.9(2) . . ? C6 C1 C7 118.2(2) . . ? C3 C2 C1 120.8(2) . . ? C3 C2 Cl1 116.2(2) . . ? C1 C2 Cl1 123.0(2) . . ? O2 C7 O1 122.8(2) . . ? O2 C7 C1 124.0(2) . . ? O1 C7 C1 113.2(2) . . ? C6 C5 C4 119.1(2) . . ? C3 C4 C5 120.5(2) . . ? _diffrn_measured_fraction_theta_max 0.904 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.316 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.058 #===END data_toluic_acid:chlorobenzoic_acid_cocrystal_at_150K _database_code_depnum_ccdc_archive 'CCDC 694060' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H13 Cl O4' _chemical_formula_weight 292.70 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 3.8267(3) _cell_length_b 23.260(2) _cell_length_c 7.65020(10) _cell_angle_alpha 90.00 _cell_angle_beta 104.372(7) _cell_angle_gamma 90.00 _cell_volume 659.63(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.91628 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15213 _diffrn_reflns_av_R_equivalents 0.0783 _diffrn_reflns_av_sigmaI/netI 0.0544 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 29.41 _reflns_number_total 3168 _reflns_number_gt 2700 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 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^)+(0.0721P)^2^+0.1629P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(9) _refine_ls_number_reflns 3168 _refine_ls_number_parameters 171 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0551 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1235 _refine_ls_wR_factor_gt 0.1141 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.953 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.002 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 C1 C 0.7415(5) 0.35877(7) 0.09233(18) 0.0225(5) Uani 1 1 d GD . . C2 C 0.6040(5) 0.39509(6) -0.0527(2) 0.0292(6) Uani 1 1 d G A . H2 H 0.5114 0.4308 -0.0334 0.035 Uiso 1 1 calc R . . C3 C 0.6049(5) 0.37797(8) -0.2267(2) 0.0328(6) Uani 1 1 d G A . H3 H 0.5129 0.4023 -0.3238 0.039 Uiso 1 1 calc R . . C4 C 0.7433(5) 0.32454(8) -0.25562(17) 0.0316(6) Uani 1 1 d G A . H4 H 0.7439 0.3131 -0.3720 0.038 Uiso 1 1 calc R . . C5 C 0.8808(5) 0.28822(7) -0.1106(2) 0.0261(5) Uani 1 1 d G A . H5 H 0.9734 0.2525 -0.1299 0.031 Uiso 1 1 calc R . . C6 C 0.8799(4) 0.30533(6) 0.06341(18) 0.0229(5) Uani 1 1 d G A . C7 C 1.0277(7) 0.26375(12) 0.2130(3) 0.0232(5) Uani 1 1 d . . . O1 O 0.9938(6) 0.26920(10) 0.3672(2) 0.0377(5) Uani 1 1 d . A . O2 O 1.1985(6) 0.22011(9) 0.1640(3) 0.0343(5) Uani 1 1 d . A . H200 H 1.261(10) 0.1926(17) 0.278(5) 0.051 Uiso 1 1 d . . . Cl1 Cl 0.7272(13) 0.38489(18) 0.3028(4) 0.0243(3) Uani 0.50 1 d P A 1 C101 C 0.728(7) 0.3816(10) 0.2757(17) 0.0243(3) Uani 0.50 1 d PD A 2 H10A H 0.6304 0.4199 0.2630 0.036 Uiso 0.50 1 calc PR A 2 H10B H 0.9666 0.3822 0.3536 0.036 Uiso 0.50 1 calc PR A 2 H10C H 0.5766 0.3572 0.3269 0.036 Uiso 0.50 1 calc PR A 2 C8 C 1.6954(4) 0.05739(7) 0.70313(16) 0.0238(5) Uani 1 1 d GD . . C9 C 1.8458(5) 0.02212(6) 0.8491(2) 0.0275(6) Uani 1 1 d G B . H9 H 1.9358 -0.0138 0.8299 0.033 Uiso 1 1 calc R . . C10 C 1.8619(5) 0.04061(8) 1.02368(18) 0.0294(6) Uani 1 1 d G B . H10 H 1.9625 0.0170 1.1213 0.035 Uiso 1 1 calc R . . C11 C 1.7274(5) 0.09436(8) 1.05233(16) 0.0302(6) Uani 1 1 d G B . H11 H 1.7382 0.1067 1.1692 0.036 Uiso 1 1 calc R . . C12 C 1.5770(5) 0.12963(6) 0.9064(2) 0.0258(5) Uani 1 1 d G B . H12 H 1.4870 0.1656 0.9256 0.031 Uiso 1 1 calc R . . C13 C 1.5609(4) 0.11115(6) 0.73179(18) 0.0220(5) Uani 1 1 d G B . C14 C 1.4082(7) 0.15196(11) 0.5815(3) 0.0245(5) Uani 1 1 d . . . O3 O 1.4383(6) 0.14639(10) 0.4275(2) 0.0367(5) Uani 1 1 d . B . O4 O 1.2410(6) 0.19608(9) 0.6314(3) 0.0352(5) Uani 1 1 d . B . H400 H 1.131(10) 0.2156(18) 0.543(5) 0.053 Uiso 1 1 d . . . Cl2 Cl 1.6747(12) 0.02856(16) 0.4890(3) 0.0310(4) Uani 0.50 1 d P B 1 C102 C 1.698(6) 0.0335(9) 0.5199(16) 0.0310(4) Uani 0.50 1 d PD B 2 H10D H 1.7842 -0.0054 0.5328 0.047 Uiso 0.50 1 calc PR B 2 H10E H 1.8535 0.0564 0.4672 0.047 Uiso 0.50 1 calc PR B 2 H10F H 1.4576 0.0343 0.4434 0.047 Uiso 0.50 1 calc PR B 2 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 C1 0.0212(12) 0.0221(11) 0.0252(12) -0.0019(9) 0.0079(10) -0.0019(9) C2 0.0277(12) 0.0275(14) 0.0330(14) 0.0042(11) 0.0087(11) 0.0028(10) C3 0.0330(13) 0.0355(15) 0.0295(13) 0.0106(12) 0.0068(11) 0.0038(12) C4 0.0365(14) 0.0345(15) 0.0247(13) -0.0013(10) 0.0094(11) -0.0021(11) C5 0.0286(12) 0.0252(13) 0.0263(12) -0.0004(10) 0.0104(10) -0.0004(10) C6 0.0219(11) 0.0224(12) 0.0247(12) 0.0005(9) 0.0063(9) -0.0015(9) C7 0.0225(12) 0.0225(11) 0.0255(12) 0.0002(10) 0.0078(10) -0.0013(9) O1 0.0543(13) 0.0376(11) 0.0242(10) 0.0052(8) 0.0156(9) 0.0169(9) O2 0.0496(12) 0.0289(11) 0.0262(10) 0.0020(8) 0.0130(9) 0.0135(9) Cl1 0.0346(5) 0.0222(8) 0.0193(10) -0.0022(8) 0.0126(10) 0.0041(5) C101 0.0346(5) 0.0222(8) 0.0193(10) -0.0022(8) 0.0126(10) 0.0041(5) C8 0.0219(11) 0.0239(12) 0.0259(12) -0.0019(10) 0.0068(10) -0.0030(9) C9 0.0256(12) 0.0240(14) 0.0331(13) 0.0006(11) 0.0077(10) -0.0009(10) C10 0.0291(13) 0.0271(14) 0.0313(14) 0.0068(10) 0.0061(11) -0.0009(10) C11 0.0324(14) 0.0331(15) 0.0255(13) 0.0008(10) 0.0078(10) -0.0047(10) C12 0.0267(12) 0.0248(13) 0.0262(12) -0.0021(10) 0.0072(10) -0.0007(10) C13 0.0204(11) 0.0223(12) 0.0238(11) 0.0007(9) 0.0065(9) -0.0013(9) C14 0.0241(12) 0.0220(12) 0.0278(13) -0.0012(10) 0.0075(10) 0.0005(9) O3 0.0516(12) 0.0345(11) 0.0257(10) 0.0048(8) 0.0127(9) 0.0176(9) O4 0.0522(13) 0.0270(12) 0.0282(10) 0.0055(8) 0.0131(9) 0.0177(9) Cl2 0.0437(9) 0.0260(10) 0.0248(11) -0.0041(8) 0.0113(11) 0.0084(6) C102 0.0437(9) 0.0260(10) 0.0248(11) -0.0041(8) 0.0113(11) 0.0084(6) _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 C1 C2 1.3900 . ? C1 C6 1.3900 . ? C1 C101 1.513(9) . ? C1 Cl1 1.734(2) . ? C2 C3 1.3900 . ? C2 H2 0.9300 . ? C3 C4 1.3900 . ? C3 H3 0.9300 . ? C4 C5 1.3900 . ? C4 H4 0.9300 . ? C5 C6 1.3900 . ? C5 H5 0.9300 . ? C6 C7 1.498(3) . ? C7 O1 1.225(3) . ? C7 O2 1.311(3) . ? O2 H200 1.06(4) . ? C101 H10A 0.9600 . ? C101 H10B 0.9600 . ? C101 H10C 0.9600 . ? C8 C9 1.3900 . ? C8 C13 1.3900 . ? C8 C102 1.510(8) . ? C8 Cl2 1.754(2) . ? C9 C10 1.3900 . ? C9 H9 0.9300 . ? C10 C11 1.3900 . ? C10 H10 0.9300 . ? C11 C12 1.3900 . ? C11 H11 0.9300 . ? C12 C13 1.3900 . ? C12 H12 0.9300 . ? C13 C14 1.494(3) . ? C14 O3 1.219(3) . ? C14 O4 1.315(3) . ? O4 H400 0.84(4) . ? C102 H10D 0.9600 . ? C102 H10E 0.9600 . ? C102 H10F 0.9600 . ? 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 C1 C6 120.0 . . ? C2 C1 C101 115.7(9) . . ? C6 C1 C101 124.3(9) . . ? C2 C1 Cl1 115.80(19) . . ? C6 C1 Cl1 124.20(19) . . ? C101 C1 Cl1 0.2(12) . . ? C3 C2 C1 120.0 . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C4 C3 C2 120.0 . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 120.0 . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 120.0 . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 120.0 . . ? C5 C6 C7 117.15(14) . . ? C1 C6 C7 122.84(14) . . ? O1 C7 O2 122.3(2) . . ? O1 C7 C6 124.0(2) . . ? O2 C7 C6 113.7(2) . . ? C7 O2 H200 105(2) . . ? C1 C101 H10A 109.5 . . ? C1 C101 H10B 109.5 . . ? H10A C101 H10B 109.5 . . ? C1 C101 H10C 109.4 . . ? H10A C101 H10C 109.5 . . ? H10B C101 H10C 109.5 . . ? C9 C8 C13 120.0 . . ? C9 C8 C102 115.6(9) . . ? C13 C8 C102 124.4(9) . . ? C9 C8 Cl2 116.00(17) . . ? C13 C8 Cl2 123.96(17) . . ? C102 C8 Cl2 3.0(10) . . ? C10 C9 C8 120.0 . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 120.0 . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C11 C10 120.0 . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C13 C12 C11 120.0 . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C8 120.0 . . ? C12 C13 C14 117.30(14) . . ? C8 C13 C14 122.67(14) . . ? O3 C14 O4 122.2(2) . . ? O3 C14 C13 124.3(2) . . ? O4 C14 C13 113.5(2) . . ? C14 O4 H400 112(3) . . ? C8 C102 H10D 109.5 . . ? C8 C102 H10E 109.5 . . ? H10D C102 H10E 109.5 . . ? C8 C102 H10F 109.5 . . ? H10D C102 H10F 109.5 . . ? H10E C102 H10F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.904 _diffrn_reflns_theta_full 29.41 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.320 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.060 # Attachment 'B811438B_toluic-chlorobenzoic-cocrystal.cif' data_o-toluic_acid_RT _database_code_depnum_ccdc_archive 'CCDC 694061' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H8 O2' _chemical_formula_weight 136.14 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' _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 4.831(3) _cell_length_b 19.420(6) _cell_length_c 7.7608(19) _cell_angle_alpha 90.00 _cell_angle_beta 106.87(3) _cell_angle_gamma 90.00 _cell_volume 696.7(5) _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 plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1313 _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_sigmaI/netI 0.0548 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 24.97 _reflns_number_total 1225 _reflns_number_gt 654 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 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^)+(0.1813P)^2^+2.1338P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.045(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1225 _refine_ls_number_parameters 92 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1211 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.2296 _refine_ls_wR_factor_gt 0.1368 _refine_ls_goodness_of_fit_ref 0.622 _refine_ls_restrained_S_all 0.622 _refine_ls_shift/su_max 0.021 _refine_ls_shift/su_mean 0.003 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 C8 C 0.6332(10) 0.3310(2) 0.5510(6) 0.0697(13) Uani 1 1 d . . . H8A H 0.7671 0.2932 0.5752 0.105 Uiso 1 1 calc R . . H8B H 0.4553 0.3169 0.5720 0.105 Uiso 1 1 calc R . . H8C H 0.7142 0.3689 0.6290 0.105 Uiso 1 1 calc R . . C1 C 0.3889(7) 0.40641(18) 0.2775(5) 0.0459(9) Uani 1 1 d . . . C2 C 0.5754(8) 0.3530(2) 0.3590(5) 0.0497(10) Uani 1 1 d . . . C3 C 0.7152(9) 0.3182(2) 0.2508(6) 0.0592(11) Uani 1 1 d . . . H3 H 0.8380 0.2819 0.3003 0.071 Uiso 1 1 calc R . . C4 C 0.6785(9) 0.3356(2) 0.0738(6) 0.0626(12) Uani 1 1 d . . . H4 H 0.7777 0.3116 0.0065 0.075 Uiso 1 1 calc R . . C5 C 0.4958(10) 0.3881(2) -0.0032(6) 0.0676(12) Uani 1 1 d . . . H5 H 0.4693 0.4000 -0.1230 0.081 Uiso 1 1 calc R . . C6 C 0.3519(9) 0.4233(2) 0.0983(5) 0.0584(11) Uani 1 1 d . . . H6 H 0.2275 0.4590 0.0461 0.070 Uiso 1 1 calc R . . C7 C 0.2243(7) 0.44730(19) 0.3774(5) 0.0465(9) Uani 1 1 d . . . O1 O 0.2452(6) 0.43821(15) 0.5367(4) 0.0630(9) Uani 1 1 d . . . O2 O 0.0552(6) 0.49437(15) 0.2820(4) 0.0648(9) Uani 1 1 d . . . H100 H -0.0917 0.5231 0.3450 0.374 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 C8 0.079(3) 0.072(3) 0.066(3) 0.013(2) 0.032(2) 0.020(2) C1 0.0399(18) 0.052(2) 0.050(2) -0.0043(17) 0.0189(16) -0.0038(15) C2 0.047(2) 0.053(2) 0.054(2) -0.0024(17) 0.0228(18) -0.0036(16) C3 0.058(2) 0.054(2) 0.071(3) -0.001(2) 0.027(2) 0.0090(18) C4 0.062(3) 0.070(3) 0.066(3) -0.010(2) 0.034(2) 0.004(2) C5 0.072(3) 0.089(3) 0.049(2) -0.003(2) 0.029(2) 0.008(2) C6 0.053(2) 0.077(3) 0.050(2) 0.003(2) 0.0212(18) 0.013(2) C7 0.0378(18) 0.058(2) 0.046(2) -0.0003(18) 0.0154(16) -0.0020(16) O1 0.0604(18) 0.083(2) 0.0515(17) 0.0051(14) 0.0256(13) 0.0235(14) O2 0.0645(17) 0.079(2) 0.0568(17) 0.0112(15) 0.0275(14) 0.0240(15) _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 C8 C2 1.497(5) . ? C1 C6 1.389(5) . ? C1 C2 1.399(5) . ? C1 C7 1.491(5) . ? C2 C3 1.395(5) . ? C3 C4 1.375(6) . ? C4 C5 1.369(6) . ? C5 C6 1.374(6) . ? C7 O1 1.223(4) . ? C7 O2 1.304(4) . ? 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 C6 C1 C2 120.5(3) . . ? C6 C1 C7 117.5(3) . . ? C2 C1 C7 122.0(3) . . ? C1 C2 C3 116.6(4) . . ? C1 C2 C8 124.8(3) . . ? C3 C2 C8 118.5(4) . . ? C4 C3 C2 122.5(4) . . ? C3 C4 C5 119.9(4) . . ? C4 C5 C6 119.4(4) . . ? C5 C6 C1 121.1(4) . . ? O1 C7 O2 122.0(3) . . ? O1 C7 C1 123.3(3) . . ? O2 C7 C1 114.7(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.174 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.053