Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Scott Childs' _publ_contact_author_address ; SSCI, Inc. 3065 Kent Ave. West Lafayette IN 47906 UNITED STATES OF AMERICA ; _publ_contact_author_email SCOTT.CHILDS@APTUIT.COM _publ_section_title ; Cocrystals of chlorzoxazone with carboxylic acids ; _publ_author_name 'Scott Childs' data_a13g120 _database_code_depnum_ccdc_archive 'CCDC 638925' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-Chloro-2(3H)-benzoxazolone 2,4-dihydroxybenzoic acid ; _chemical_name_common '5-Chloro-2(3H)-benzoxazolone 2,4-dihydroxybenzoic acid' _chemical_melting_point 452.3 _chemical_formula_moiety 'C7 H4 Cl N O2, C7 H6 O4' _chemical_formula_sum 'C14 H10 Cl N O6' _chemical_formula_weight 323.68 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' Cl Cl 0.3639 0.7018 '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 6.7431(5) _cell_length_b 8.0503(6) _cell_length_c 13.8001(10) _cell_angle_alpha 77.722(3) _cell_angle_beta 88.476(2) _cell_angle_gamma 66.354(2) _cell_volume 669.09(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1206 _cell_measurement_theta_min 3.26 _cell_measurement_theta_max 66.81 _exptl_crystal_description rhomboid _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 2.840 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6289 _exptl_absorpt_correction_T_max 0.7643 _exptl_absorpt_process_details 'SADABS V2.10, Sheldrick 2003' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3349 _diffrn_reflns_av_R_equivalents 0.0211 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 67.05 _reflns_number_total 2014 _reflns_number_gt 1801 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0523P)^2^+0.3796P] 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 2014 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.0991 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 C1 C 1.0240(4) 0.3811(3) 0.92023(17) 0.0275(5) Uani 1 1 d . . . C2 C 0.7486(4) 0.5270(3) 0.80295(16) 0.0243(5) Uani 1 1 d . . . C3 C 0.5632(4) 0.5881(3) 0.74138(17) 0.0271(5) Uani 1 1 d . . . H3 H 0.4515 0.5453 0.7573 0.033 Uiso 1 1 calc R . . C4 C 0.5525(4) 0.7173(3) 0.65423(17) 0.0270(5) Uani 1 1 d . . . C5 C 0.7103(4) 0.7852(3) 0.63074(17) 0.0302(5) Uani 1 1 d . . . H5 H 0.6926 0.8753 0.5710 0.036 Uiso 1 1 calc R . . C6 C 0.8949(4) 0.7225(3) 0.69394(18) 0.0305(5) Uani 1 1 d . . . H6 H 1.0045 0.7684 0.6796 0.037 Uiso 1 1 calc R . . C7 C 0.9100(4) 0.5909(3) 0.77795(17) 0.0261(5) Uani 1 1 d . . . C8 C 0.5983(4) 0.8753(3) 0.24492(16) 0.0241(5) Uani 1 1 d . . . C9 C 0.5200(4) 1.0048(3) 0.15586(17) 0.0261(5) Uani 1 1 d . . . H9 H 0.3814 1.0310 0.1269 0.031 Uiso 1 1 calc R . . C10 C 0.6436(4) 1.0954(3) 0.10945(17) 0.0259(5) Uani 1 1 d . . . C11 C 0.8486(4) 1.0585(3) 0.14986(18) 0.0285(5) Uani 1 1 d . . . H11 H 0.9322 1.1221 0.1172 0.034 Uiso 1 1 calc R . . C12 C 0.9276(4) 0.9284(3) 0.23785(17) 0.0267(5) Uani 1 1 d . . . H12 H 1.0676 0.9015 0.2654 0.032 Uiso 1 1 calc R . . C13 C 0.8051(4) 0.8351(3) 0.28737(16) 0.0239(5) Uani 1 1 d . . . C14 C 0.8876(4) 0.6962(3) 0.38054(16) 0.0252(5) Uani 1 1 d . . . Cl1 Cl 0.33357(10) 0.79217(9) 0.56769(4) 0.0382(2) Uani 1 1 d . . . N1 N 0.8239(3) 0.3978(3) 0.89305(14) 0.0266(4) Uani 1 1 d . . . H1 H 0.7526 0.3365 0.9270 0.032 Uiso 1 1 calc R . . O1 O 1.0802(2) 0.5000(2) 0.84980(11) 0.0297(4) Uani 1 1 d . . . O2 O 1.1432(3) 0.2829(2) 0.99297(12) 0.0334(4) Uani 1 1 d . . . O3 O 0.4691(3) 0.7921(2) 0.28728(13) 0.0359(4) Uani 1 1 d . . . O4 O 0.5709(3) 1.2255(2) 0.02234(12) 0.0336(4) Uani 1 1 d . . . O5 O 0.7832(3) 0.6090(2) 0.42390(12) 0.0305(4) Uani 1 1 d . . . O6 O 1.0802(3) 0.6694(2) 0.41549(12) 0.0325(4) Uani 1 1 d . . . H4O H 0.4465 1.2436 0.0085 0.039 Uiso 1 1 d R . . H3O H 0.5444 0.7107 0.3431 0.039 Uiso 1 1 d R . . H6O H 1.1195 0.5786 0.4665 0.039 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 C1 0.0279(13) 0.0279(12) 0.0255(13) -0.0068(10) 0.0037(10) -0.0098(11) C2 0.0255(12) 0.0235(11) 0.0229(12) -0.0040(9) 0.0033(9) -0.0094(10) C3 0.0275(12) 0.0295(12) 0.0268(13) -0.0056(10) 0.0042(9) -0.0145(10) C4 0.0276(13) 0.0279(12) 0.0235(12) -0.0054(10) 0.0005(9) -0.0092(10) C5 0.0368(14) 0.0283(12) 0.0238(13) 0.0015(10) 0.0040(10) -0.0151(11) C6 0.0314(13) 0.0330(13) 0.0310(14) -0.0050(11) 0.0056(10) -0.0184(11) C7 0.0233(12) 0.0265(12) 0.0281(13) -0.0076(10) 0.0008(9) -0.0087(10) C8 0.0245(12) 0.0228(11) 0.0264(12) -0.0050(9) 0.0030(9) -0.0110(10) C9 0.0226(12) 0.0253(11) 0.0280(13) -0.0032(10) -0.0048(9) -0.0081(10) C10 0.0278(13) 0.0242(11) 0.0222(12) -0.0017(9) 0.0002(9) -0.0085(10) C11 0.0257(12) 0.0283(12) 0.0312(13) -0.0006(10) 0.0022(9) -0.0134(11) C12 0.0236(12) 0.0284(12) 0.0278(13) -0.0046(10) -0.0007(9) -0.0107(10) C13 0.0237(12) 0.0215(11) 0.0248(12) -0.0046(9) 0.0009(9) -0.0076(10) C14 0.0251(12) 0.0247(11) 0.0235(12) -0.0058(9) 0.0005(9) -0.0075(10) Cl1 0.0361(4) 0.0490(4) 0.0275(4) 0.0041(3) -0.0051(2) -0.0211(3) N1 0.0267(10) 0.0269(10) 0.0249(10) 0.0002(8) 0.0023(8) -0.0123(9) O1 0.0259(9) 0.0348(9) 0.0288(9) -0.0055(7) 0.0014(7) -0.0133(8) O2 0.0296(9) 0.0363(9) 0.0279(10) -0.0012(8) -0.0044(7) -0.0094(8) O3 0.0303(9) 0.0393(10) 0.0362(10) 0.0078(8) -0.0060(7) -0.0197(8) O4 0.0281(9) 0.0372(10) 0.0288(9) 0.0084(7) -0.0054(7) -0.0139(8) O5 0.0279(9) 0.0322(9) 0.0281(9) 0.0028(7) -0.0004(7) -0.0134(8) O6 0.0291(9) 0.0349(9) 0.0274(9) 0.0081(7) -0.0090(7) -0.0137(8) _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 O2 1.214(3) . ? C1 N1 1.356(3) . ? C1 O1 1.371(3) . ? C2 C3 1.383(3) . ? C2 C7 1.386(3) . ? C2 N1 1.395(3) . ? C3 C4 1.395(3) . ? C3 H3 0.9500 . ? C4 C5 1.382(3) . ? C4 Cl1 1.744(2) . ? C5 C6 1.389(3) . ? C5 H5 0.9500 . ? C6 C7 1.369(3) . ? C6 H6 0.9500 . ? C7 O1 1.383(3) . ? C8 O3 1.350(3) . ? C8 C9 1.387(3) . ? C8 C13 1.412(3) . ? C9 C10 1.378(3) . ? C9 H9 0.9500 . ? C10 O4 1.366(3) . ? C10 C11 1.397(3) . ? C11 C12 1.379(3) . ? C11 H11 0.9500 . ? C12 C13 1.401(3) . ? C12 H12 0.9500 . ? C13 C14 1.463(3) . ? C14 O5 1.241(3) . ? C14 O6 1.316(3) . ? N1 H1 0.8800 . ? O3 H3O 0.9053 . ? O4 H4O 0.8123 . ? O6 H6O 0.8580 . ? 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 O2 C1 N1 129.5(2) . . ? O2 C1 O1 122.0(2) . . ? N1 C1 O1 108.45(19) . . ? C3 C2 C7 121.4(2) . . ? C3 C2 N1 133.0(2) . . ? C7 C2 N1 105.5(2) . . ? C2 C3 C4 115.0(2) . . ? C2 C3 H3 122.5 . . ? C4 C3 H3 122.5 . . ? C5 C4 C3 123.5(2) . . ? C5 C4 Cl1 117.75(18) . . ? C3 C4 Cl1 118.70(18) . . ? C4 C5 C6 120.5(2) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C7 C6 C5 116.3(2) . . ? C7 C6 H6 121.8 . . ? C5 C6 H6 121.8 . . ? C6 C7 O1 127.7(2) . . ? C6 C7 C2 123.2(2) . . ? O1 C7 C2 109.1(2) . . ? O3 C8 C9 117.1(2) . . ? O3 C8 C13 122.8(2) . . ? C9 C8 C13 120.1(2) . . ? C10 C9 C8 119.8(2) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? O4 C10 C9 121.5(2) . . ? O4 C10 C11 117.2(2) . . ? C9 C10 C11 121.3(2) . . ? C12 C11 C10 119.0(2) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C11 C12 C13 121.1(2) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C12 C13 C8 118.7(2) . . ? C12 C13 C14 121.7(2) . . ? C8 C13 C14 119.6(2) . . ? O5 C14 O6 122.1(2) . . ? O5 C14 C13 122.4(2) . . ? O6 C14 C13 115.6(2) . . ? C1 N1 C2 109.52(19) . . ? C1 N1 H1 125.2 . . ? C2 N1 H1 125.2 . . ? C1 O1 C7 107.41(17) . . ? C8 O3 H3O 106.0 . . ? C10 O4 H4O 109.1 . . ? C14 O6 H6O 108.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O6 H6O O5 0.86 1.81 2.669(2) 176.3 2_766 O3 H3O O5 0.91 1.78 2.596(2) 149.2 . O4 H4O O2 0.81 1.95 2.759(2) 172.8 1_464 N1 H1 O4 0.88 2.08 2.950(2) 170.1 1_546 _diffrn_measured_fraction_theta_max 0.843 _diffrn_reflns_theta_full 67.05 _diffrn_measured_fraction_theta_full 0.843 _refine_diff_density_max 0.241 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.092