# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_EA+SA _database_code_depnum_ccdc_archive 'CCDC 752480' _audit_creation_method SHELXL-97 _chemical_name_systematic ; cocrystal of ethenzamide with salicylic acid ; _chemical_name_common ; 1:1 ethenzamide and salicylic acid cocrystal ; _chemical_melting_point ? _chemical_formula_moiety 'C9 H11 N O2, C7 H6 O3' _chemical_formula_sum 'C16 H17 N O5' _chemical_formula_weight 303.31 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' 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 P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' 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 10.679(2) _cell_length_b 9.6670(19) _cell_length_c 14.845(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.97(3) _cell_angle_gamma 90.00 _cell_volume 1465.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4696 _cell_measurement_theta_min 2.0888 _cell_measurement_theta_max 31.0560 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9669 _exptl_absorpt_correction_T_max 0.9797 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10945 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3604 _reflns_number_gt 3128 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _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^)+(0.0966P)^2^+0.4882P] 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 3604 _refine_ls_number_parameters 216 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0845 _refine_ls_R_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.1950 _refine_ls_wR_factor_gt 0.1845 _refine_ls_goodness_of_fit_ref 1.176 _refine_ls_restrained_S_all 1.176 _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 O2 O 0.23358(14) 1.16134(14) 1.07419(10) 0.0311(4) Uani 1 1 d . . . O4 O 0.25727(14) 0.34529(15) 0.88468(10) 0.0326(4) Uani 1 1 d . . . O5 O 0.29416(15) 0.40139(15) 1.03649(10) 0.0315(4) Uani 1 1 d . . . O1 O 0.08483(14) 0.80823(14) 0.91886(10) 0.0303(3) Uani 1 1 d . . . N1 N 0.18988(17) 1.06140(18) 0.93149(12) 0.0288(4) Uani 1 1 d . . . O3 O 0.30789(16) 0.52267(16) 0.76974(10) 0.0367(4) Uani 1 1 d . . . C7 C 0.19483(17) 1.0590(2) 1.02131(14) 0.0254(4) Uani 1 1 d . . . C16 C 0.29546(17) 0.4290(2) 0.95036(13) 0.0255(4) Uani 1 1 d . . . C6 C 0.17206(18) 0.9355(2) 1.16041(14) 0.0291(4) Uani 1 1 d . . . H6 H 0.2062 1.0171 1.1944 0.035 Uiso 1 1 calc R . . C15 C 0.3906(2) 0.6591(2) 1.01145(15) 0.0303(4) Uani 1 1 d . . . H15 H 0.3886 0.6330 1.0727 0.036 Uiso 1 1 calc R . . C1 C 0.15484(17) 0.93108(19) 1.06356(13) 0.0245(4) Uani 1 1 d . . . C10 C 0.34536(18) 0.56705(19) 0.93624(13) 0.0257(4) Uani 1 1 d . . . C2 C 0.10263(19) 0.8104(2) 1.01394(14) 0.0267(4) Uani 1 1 d . . . C3 C 0.0712(2) 0.6983(2) 1.06197(15) 0.0321(5) Uani 1 1 d . . . H3 H 0.0364 0.6164 1.0286 0.038 Uiso 1 1 calc R . . C12 C 0.39698(19) 0.7368(2) 0.83245(15) 0.0310(4) Uani 1 1 d . . . H12 H 0.3991 0.7644 0.7715 0.037 Uiso 1 1 calc R . . C11 C 0.34953(18) 0.6062(2) 0.84582(14) 0.0274(4) Uani 1 1 d . . . C13 C 0.4407(2) 0.8254(2) 0.90758(16) 0.0342(5) Uani 1 1 d . . . H13 H 0.4733 0.9140 0.8980 0.041 Uiso 1 1 calc R . . C8 C 0.0172(2) 0.6929(2) 0.86502(15) 0.0314(5) Uani 1 1 d . . . H8A H -0.0706 0.6823 0.8740 0.038 Uiso 1 1 calc R . . H8B H 0.0671 0.6064 0.8853 0.038 Uiso 1 1 calc R . . C14 C 0.4381(2) 0.7874(2) 0.99734(16) 0.0342(5) Uani 1 1 d . . . H14 H 0.4688 0.8495 1.0487 0.041 Uiso 1 1 calc R . . C9 C 0.0050(2) 0.7227(3) 0.76341(16) 0.0382(5) Uani 1 1 d . . . H9A H -0.0407 0.8108 0.7452 0.057 Uiso 1 1 calc R . . H9B H -0.0446 0.6484 0.7239 0.057 Uiso 1 1 calc R . . H9C H 0.0925 0.7284 0.7549 0.057 Uiso 1 1 calc R . . C4 C 0.0906(2) 0.7056(2) 1.15841(15) 0.0336(5) Uani 1 1 d . . . H4 H 0.0691 0.6283 1.1905 0.040 Uiso 1 1 calc R . . C5 C 0.1407(2) 0.8238(2) 1.20841(16) 0.0337(5) Uani 1 1 d . . . H5 H 0.1534 0.8285 1.2744 0.040 Uiso 1 1 calc R . . H2 H 0.210(3) 1.145(3) 0.907(2) 0.051(8) Uiso 1 1 d . . . H1 H 0.152(3) 0.987(3) 0.893(2) 0.049(8) Uiso 1 1 d . . . H7 H 0.285(3) 0.441(4) 0.792(2) 0.073(10) Uiso 1 1 d . . . H10 H 0.267(3) 0.304(3) 1.042(2) 0.066(9) 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 O2 0.0390(8) 0.0281(7) 0.0265(8) -0.0017(6) 0.0100(6) -0.0056(6) O4 0.0424(8) 0.0291(8) 0.0252(8) -0.0010(6) 0.0080(6) -0.0056(6) O5 0.0451(8) 0.0265(8) 0.0248(7) 0.0002(6) 0.0132(6) -0.0026(6) O1 0.0390(8) 0.0270(7) 0.0249(7) -0.0021(6) 0.0091(6) -0.0026(6) N1 0.0377(9) 0.0250(9) 0.0248(9) -0.0001(7) 0.0106(7) -0.0004(7) O3 0.0545(9) 0.0314(8) 0.0243(7) -0.0014(6) 0.0117(7) -0.0078(7) C7 0.0244(8) 0.0251(9) 0.0268(10) 0.0016(7) 0.0079(7) 0.0016(7) C16 0.0250(8) 0.0257(9) 0.0255(9) 0.0000(7) 0.0069(7) 0.0013(7) C6 0.0287(9) 0.0313(10) 0.0268(10) 0.0015(8) 0.0070(7) -0.0013(8) C15 0.0345(10) 0.0272(10) 0.0284(10) -0.0017(8) 0.0080(8) 0.0017(8) C1 0.0234(8) 0.0253(9) 0.0244(9) 0.0023(7) 0.0063(7) 0.0021(7) C10 0.0259(8) 0.0247(9) 0.0262(10) -0.0001(7) 0.0071(7) 0.0008(7) C2 0.0286(9) 0.0269(10) 0.0243(10) 0.0013(7) 0.0073(7) 0.0042(7) C3 0.0359(10) 0.0262(10) 0.0343(11) 0.0015(8) 0.0106(8) -0.0003(8) C12 0.0323(10) 0.0295(10) 0.0314(10) 0.0063(8) 0.0098(8) 0.0023(8) C11 0.0290(9) 0.0269(10) 0.0256(10) 0.0004(8) 0.0071(7) 0.0017(7) C13 0.0337(10) 0.0252(10) 0.0431(13) 0.0037(9) 0.0104(9) -0.0010(8) C8 0.0309(10) 0.0290(10) 0.0344(11) -0.0065(8) 0.0099(8) -0.0048(8) C14 0.0387(11) 0.0264(10) 0.0355(12) -0.0046(9) 0.0077(9) -0.0003(8) C9 0.0396(11) 0.0414(12) 0.0335(12) -0.0105(10) 0.0104(9) -0.0072(9) C4 0.0356(10) 0.0314(10) 0.0351(12) 0.0098(9) 0.0121(9) 0.0017(8) C5 0.0340(10) 0.0400(12) 0.0267(10) 0.0059(9) 0.0080(8) -0.0001(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 O2 C7 1.255(2) . ? O4 C16 1.241(2) . ? O5 C16 1.310(2) . ? O5 H10 0.99(3) . ? O1 C2 1.368(2) . ? O1 C8 1.437(2) . ? N1 C7 1.319(3) . ? N1 H2 0.93(3) . ? N1 H1 0.93(3) . ? O3 C11 1.353(2) . ? O3 H7 0.92(3) . ? C7 C1 1.504(3) . ? C16 C10 1.474(3) . ? C6 C5 1.387(3) . ? C6 C1 1.396(3) . ? C6 H6 0.9500 . ? C15 C14 1.379(3) . ? C15 C10 1.399(3) . ? C15 H15 0.9500 . ? C1 C2 1.405(3) . ? C10 C11 1.408(3) . ? C2 C3 1.391(3) . ? C3 C4 1.387(3) . ? C3 H3 0.9500 . ? C12 C13 1.376(3) . ? C12 C11 1.396(3) . ? C12 H12 0.9500 . ? C13 C14 1.390(3) . ? C13 H13 0.9500 . ? C8 C9 1.504(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C14 H14 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C4 C5 1.383(3) . ? C4 H4 0.9500 . ? 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 C16 O5 H10 111.1(19) . . ? C2 O1 C8 118.78(16) . . ? C7 N1 H2 117.6(17) . . ? C7 N1 H1 119.2(18) . . ? H2 N1 H1 122(2) . . ? C11 O3 H7 105(2) . . ? O2 C7 N1 121.81(18) . . ? O2 C7 C1 117.97(17) . . ? N1 C7 C1 120.22(17) . . ? O4 C16 O5 122.63(18) . . ? O4 C16 C10 121.88(18) . . ? O5 C16 C10 115.49(17) . . ? C5 C6 C1 121.76(19) . . ? C5 C6 H6 119.1 . . ? C1 C6 H6 119.1 . . ? C14 C15 C10 120.5(2) . . ? C14 C15 H15 119.8 . . ? C10 C15 H15 119.8 . . ? C6 C1 C2 118.56(18) . . ? C6 C1 C7 115.88(17) . . ? C2 C1 C7 125.57(18) . . ? C15 C10 C11 119.38(18) . . ? C15 C10 C16 121.14(18) . . ? C11 C10 C16 119.47(17) . . ? O1 C2 C3 122.35(18) . . ? O1 C2 C1 117.89(17) . . ? C3 C2 C1 119.76(18) . . ? C4 C3 C2 120.2(2) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C13 C12 C11 119.97(19) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? O3 C11 C12 117.72(18) . . ? O3 C11 C10 122.78(18) . . ? C12 C11 C10 119.49(18) . . ? C12 C13 C14 121.03(19) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? O1 C8 C9 106.95(17) . . ? O1 C8 H8A 110.3 . . ? C9 C8 H8A 110.3 . . ? O1 C8 H8B 110.3 . . ? C9 C8 H8B 110.3 . . ? H8A C8 H8B 108.6 . . ? C15 C14 C13 119.6(2) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C5 C4 C3 120.9(2) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 118.8(2) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.447 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.063 data_EA+CNBA _database_code_depnum_ccdc_archive 'CCDC 752481' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1:1 cocrystal of ethenzamide and 2-chloro-4-nitrobenzoic acid ; _chemical_name_common ; 1:1 cocrystal of ethenzamide and 2-chloro-4-nitrobenzoic acid ; _chemical_melting_point ? _chemical_formula_moiety 'C9 H11 N O2, C7 H4 Cl N O4' _chemical_formula_sum 'C16 H15 Cl N2 O6' _chemical_formula_weight 366.75 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' 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' Cl Cl 0.1484 0.1585 '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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7402(15) _cell_length_b 8.3181(17) _cell_length_c 13.216(3) _cell_angle_alpha 76.02(3) _cell_angle_beta 79.85(3) _cell_angle_gamma 84.69(3) _cell_volume 811.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1837 _cell_measurement_theta_min 2.5269 _cell_measurement_theta_max 31.1948 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.501 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 0.272 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9520 _exptl_absorpt_correction_T_max 0.9603 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11687 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3994 _reflns_number_gt 3561 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _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^)+(0.0781P)^2^+0.2588P] 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 3994 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0720 _refine_ls_R_factor_gt 0.0632 _refine_ls_wR_factor_ref 0.1660 _refine_ls_wR_factor_gt 0.1588 _refine_ls_goodness_of_fit_ref 1.176 _refine_ls_restrained_S_all 1.176 _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 Cl1 Cl 1.29982(7) 0.14735(8) 1.06061(5) 0.0473(2) Uani 1 1 d . . . O2 O 0.16343(19) 0.9762(2) 0.63891(11) 0.0384(4) Uani 1 1 d . . . O3 O 1.0587(2) 0.1409(2) 0.77609(13) 0.0463(4) Uani 1 1 d . . . C15 C 0.8636(3) 0.2719(3) 0.92471(16) 0.0334(4) Uani 1 1 d . . . H15 H 0.8220 0.2625 0.8646 0.040 Uiso 1 1 calc R . . O1 O 0.63238(19) 0.71012(19) 0.57191(11) 0.0360(3) Uani 1 1 d . . . C13 C 0.8231(3) 0.3633(2) 1.08393(15) 0.0322(4) Uani 1 1 d . . . O6 O 0.7787(2) 0.4766(2) 1.23095(13) 0.0489(4) Uani 1 1 d . . . C10 C 1.0323(3) 0.2070(2) 0.94027(15) 0.0303(4) Uani 1 1 d . . . C11 C 1.0938(3) 0.2215(3) 1.03172(15) 0.0328(4) Uani 1 1 d . . . C3 C 0.5527(3) 0.6940(2) 0.40532(15) 0.0330(4) Uani 1 1 d . . . H3A H 0.6563 0.6333 0.3886 0.040 Uiso 1 1 calc R . . O5 O 0.5607(2) 0.4923(2) 1.14584(14) 0.0555(5) Uani 1 1 d . . . N1 N 0.4180(3) 0.8753(2) 0.69440(14) 0.0342(4) Uani 1 1 d . . . C16 C 1.1379(3) 0.1226(2) 0.85822(15) 0.0311(4) Uani 1 1 d . . . C7 C 0.3098(3) 0.8986(2) 0.62509(15) 0.0303(4) Uani 1 1 d . . . C1 C 0.3599(2) 0.8344(2) 0.52676(14) 0.0281(4) Uani 1 1 d . . . O4 O 1.2764(2) 0.0453(2) 0.86788(12) 0.0431(4) Uani 1 1 d . . . C6 C 0.2422(3) 0.8726(3) 0.45433(16) 0.0331(4) Uani 1 1 d . . . H6A H 0.1374 0.9321 0.4704 0.040 Uiso 1 1 calc R . . C12 C 0.9877(3) 0.3010(2) 1.10398(15) 0.0341(4) Uani 1 1 d . . . H12 H 1.0275 0.3116 1.1644 0.041 Uiso 1 1 calc R . . N2 N 0.7128(3) 0.4505(2) 1.15964(13) 0.0378(4) Uani 1 1 d . . . C2 C 0.5179(3) 0.7441(2) 0.50109(15) 0.0298(4) Uani 1 1 d . . . C14 C 0.7564(3) 0.3495(3) 0.99593(16) 0.0363(5) Uani 1 1 d . . . H14 H 0.6437 0.3910 0.9852 0.044 Uiso 1 1 calc R . . C4 C 0.4331(3) 0.7347(3) 0.33566(17) 0.0370(5) Uani 1 1 d . . . H4 H 0.4573 0.7016 0.2720 0.044 Uiso 1 1 calc R . . C8 C 0.8015(3) 0.6295(3) 0.54578(17) 0.0367(5) Uani 1 1 d . . . H8A H 0.8670 0.6951 0.4822 0.044 Uiso 1 1 calc R . . H8B H 0.7878 0.5209 0.5342 0.044 Uiso 1 1 calc R . . C5 C 0.2774(3) 0.8244(3) 0.35976(17) 0.0385(5) Uani 1 1 d . . . H5 H 0.1975 0.8518 0.3125 0.046 Uiso 1 1 calc R . . C9 C 0.8950(3) 0.6138(3) 0.6382(2) 0.0493(6) Uani 1 1 d . . . H9A H 0.9104 0.7223 0.6474 0.074 Uiso 1 1 calc R . . H9B H 1.0079 0.5574 0.6254 0.074 Uiso 1 1 calc R . . H9C H 0.8267 0.5516 0.7008 0.074 Uiso 1 1 calc R . . H2 H 0.397(4) 0.925(3) 0.748(2) 0.048(7) Uiso 1 1 d . . . H1 H 0.512(4) 0.833(4) 0.683(2) 0.054(8) Uiso 1 1 d . . . H3 H 1.109(5) 0.081(5) 0.725(3) 0.105(14) 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 Cl1 0.0377(3) 0.0664(4) 0.0454(3) -0.0247(3) -0.0135(2) 0.0037(3) O2 0.0335(7) 0.0509(9) 0.0361(8) -0.0222(7) -0.0071(6) 0.0058(6) O3 0.0456(9) 0.0656(11) 0.0369(8) -0.0307(8) -0.0142(7) 0.0143(8) C15 0.0378(10) 0.0377(10) 0.0272(9) -0.0130(8) -0.0058(8) 0.0018(8) O1 0.0340(7) 0.0432(8) 0.0330(7) -0.0151(6) -0.0078(6) 0.0086(6) C13 0.0398(11) 0.0289(9) 0.0282(10) -0.0105(7) -0.0010(8) -0.0012(8) O6 0.0555(10) 0.0582(10) 0.0408(9) -0.0284(8) -0.0041(8) -0.0030(8) C10 0.0346(10) 0.0314(9) 0.0266(9) -0.0110(7) -0.0029(8) -0.0025(8) C11 0.0347(10) 0.0360(10) 0.0290(10) -0.0097(8) -0.0039(8) -0.0054(8) C3 0.0325(10) 0.0357(10) 0.0316(10) -0.0150(8) 0.0010(8) 0.0009(8) O5 0.0560(11) 0.0679(12) 0.0431(9) -0.0232(8) -0.0103(8) 0.0260(9) N1 0.0345(9) 0.0419(9) 0.0292(9) -0.0153(7) -0.0059(7) 0.0025(8) C16 0.0326(9) 0.0355(9) 0.0258(9) -0.0085(7) -0.0035(7) -0.0029(8) C7 0.0303(9) 0.0323(9) 0.0288(9) -0.0100(8) -0.0017(7) -0.0018(7) C1 0.0284(9) 0.0309(9) 0.0261(9) -0.0106(7) -0.0015(7) -0.0014(7) O4 0.0387(8) 0.0574(10) 0.0367(8) -0.0212(7) -0.0071(6) 0.0094(7) C6 0.0269(9) 0.0409(10) 0.0343(10) -0.0150(8) -0.0050(8) 0.0010(8) C12 0.0419(11) 0.0355(10) 0.0270(10) -0.0117(8) -0.0050(8) -0.0021(8) N2 0.0492(11) 0.0351(9) 0.0279(9) -0.0099(7) -0.0011(8) 0.0016(8) C2 0.0306(9) 0.0304(9) 0.0294(9) -0.0099(7) -0.0036(7) -0.0006(7) C14 0.0380(11) 0.0403(10) 0.0325(10) -0.0141(8) -0.0063(8) 0.0051(9) C4 0.0390(11) 0.0444(11) 0.0324(10) -0.0187(9) -0.0046(8) -0.0029(9) C8 0.0294(10) 0.0406(10) 0.0397(11) -0.0114(9) -0.0058(8) 0.0065(8) C5 0.0352(10) 0.0510(12) 0.0351(11) -0.0183(9) -0.0110(9) 0.0000(9) C9 0.0403(12) 0.0598(15) 0.0491(14) -0.0149(12) -0.0140(10) 0.0107(11) _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 C11 1.729(2) . ? O2 C7 1.258(2) . ? O3 C16 1.310(2) . ? O3 H3 0.94(4) . ? C15 C14 1.382(3) . ? C15 C10 1.396(3) . ? C15 H15 0.9300 . ? O1 C2 1.363(2) . ? O1 C8 1.439(2) . ? C13 C12 1.376(3) . ? C13 C14 1.385(3) . ? C13 N2 1.480(3) . ? O6 N2 1.218(2) . ? C10 C11 1.409(3) . ? C10 C16 1.512(3) . ? C11 C12 1.397(3) . ? C3 C4 1.382(3) . ? C3 C2 1.401(3) . ? C3 H3A 0.9300 . ? O5 N2 1.228(3) . ? N1 C7 1.316(3) . ? N1 H2 0.89(3) . ? N1 H1 0.78(3) . ? C16 O4 1.209(3) . ? C7 C1 1.498(3) . ? C1 C6 1.398(3) . ? C1 C2 1.408(3) . ? C6 C5 1.378(3) . ? C6 H6A 0.9300 . ? C12 H12 0.9300 . ? C14 H14 0.9300 . ? C4 C5 1.387(3) . ? C4 H4 0.9300 . ? C8 C9 1.500(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C5 H5 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 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 C16 O3 H3 117(2) . . ? C14 C15 C10 122.00(19) . . ? C14 C15 H15 119.0 . . ? C10 C15 H15 119.0 . . ? C2 O1 C8 119.63(16) . . ? C12 C13 C14 123.15(19) . . ? C12 C13 N2 118.31(18) . . ? C14 C13 N2 118.54(19) . . ? C15 C10 C11 118.52(19) . . ? C15 C10 C16 117.77(17) . . ? C11 C10 C16 123.70(19) . . ? C12 C11 C10 120.2(2) . . ? C12 C11 Cl1 116.48(15) . . ? C10 C11 Cl1 123.34(17) . . ? C4 C3 C2 120.13(19) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C7 N1 H2 121.1(18) . . ? C7 N1 H1 121(2) . . ? H2 N1 H1 117(3) . . ? O4 C16 O3 124.11(19) . . ? O4 C16 C10 124.37(18) . . ? O3 C16 C10 111.50(17) . . ? O2 C7 N1 121.23(18) . . ? O2 C7 C1 118.41(18) . . ? N1 C7 C1 120.35(18) . . ? C6 C1 C2 118.29(18) . . ? C6 C1 C7 116.82(18) . . ? C2 C1 C7 124.85(18) . . ? C5 C6 C1 121.79(19) . . ? C5 C6 H6A 119.1 . . ? C1 C6 H6A 119.1 . . ? C13 C12 C11 118.58(19) . . ? C13 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? O6 N2 O5 124.42(19) . . ? O6 N2 C13 118.07(19) . . ? O5 N2 C13 117.51(18) . . ? O1 C2 C3 122.67(18) . . ? O1 C2 C1 117.53(17) . . ? C3 C2 C1 119.80(19) . . ? C15 C14 C13 117.6(2) . . ? C15 C14 H14 121.2 . . ? C13 C14 H14 121.2 . . ? C3 C4 C5 120.62(19) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? O1 C8 C9 106.23(18) . . ? O1 C8 H8A 110.5 . . ? C9 C8 H8A 110.5 . . ? O1 C8 H8B 110.5 . . ? C9 C8 H8B 110.5 . . ? H8A C8 H8B 108.7 . . ? C6 C5 C4 119.4(2) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.383 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.064 data_EA+VA _database_code_depnum_ccdc_archive 'CCDC 752482' _audit_creation_method SHELXL-97 _chemical_name_systematic ; cocrystal of ethenzamide with vanillic acid ; _chemical_name_common ; 1:1 ethenzamide and vanillic acid cocrystal ; _chemical_melting_point ? _chemical_formula_moiety 'C9 H11 N O2, C8 H8 O4' _chemical_formula_sum 'C17 H19 N O6' _chemical_formula_weight 333.33 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' 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 P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.774(3) _cell_length_b 14.911(3) _cell_length_c 8.0828(16) _cell_angle_alpha 90.00 _cell_angle_beta 102.87(3) _cell_angle_gamma 90.00 _cell_volume 1618.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 3643 _cell_measurement_theta_min 1.5165 _cell_measurement_theta_max 31.0181 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9741 _exptl_absorpt_correction_T_max 0.976 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12434 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4009 _reflns_number_gt 3520 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.0753P)^2^+0.4439P] 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 4009 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0832 _refine_ls_R_factor_gt 0.0737 _refine_ls_wR_factor_ref 0.1861 _refine_ls_wR_factor_gt 0.1786 _refine_ls_goodness_of_fit_ref 1.199 _refine_ls_restrained_S_all 1.199 _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 O5 O 0.38380(11) 0.23691(10) 0.1325(2) 0.0578(4) Uani 1 1 d . . . O1 O 0.88978(10) 0.83798(8) 0.78612(18) 0.0459(4) Uani 1 1 d . . . O6 O 0.54359(11) 0.17211(9) 0.35084(19) 0.0495(4) Uani 1 1 d . . . O3 O 0.65670(11) 0.56335(9) 0.4506(2) 0.0510(4) Uani 1 1 d . . . O4 O 0.73728(11) 0.44984(9) 0.6007(2) 0.0555(4) Uani 1 1 d . . . O2 O 0.87296(11) 0.55994(9) 0.7507(2) 0.0536(4) Uani 1 1 d . . . C1 C 0.95158(13) 0.69290(12) 0.8754(2) 0.0373(4) Uani 1 1 d . . . C2 C 0.96116(13) 0.78687(12) 0.8880(2) 0.0394(4) Uani 1 1 d . . . C12 C 0.53721(14) 0.26372(12) 0.3372(2) 0.0402(4) Uani 1 1 d . . . C11 C 0.60560(14) 0.32433(12) 0.4255(2) 0.0408(4) Uani 1 1 d . . . H11 H 0.6625 0.3035 0.5053 0.049 Uiso 1 1 calc R . . C3 C 1.04307(16) 0.82398(14) 1.0001(3) 0.0472(5) Uani 1 1 d . . . H3 H 1.0502 0.8873 1.0079 0.057 Uiso 1 1 calc R . . N1 N 0.79420(14) 0.68878(12) 0.6650(3) 0.0546(5) Uani 1 1 d . . . C6 C 1.02407(14) 0.64065(13) 0.9784(3) 0.0425(4) Uani 1 1 d . . . H6 H 1.0180 0.5772 0.9715 0.051 Uiso 1 1 calc R . . C10 C 0.59073(14) 0.41652(12) 0.3970(2) 0.0403(4) Uani 1 1 d . . . C4 C 1.11402(15) 0.76960(14) 1.1001(3) 0.0494(5) Uani 1 1 d . . . H4 H 1.1695 0.7959 1.1757 0.059 Uiso 1 1 calc R . . C5 C 1.10488(15) 0.67749(14) 1.0908(3) 0.0485(5) Uani 1 1 d . . . H5 H 1.1531 0.6401 1.1603 0.058 Uiso 1 1 calc R . . C13 C 0.45229(15) 0.29456(13) 0.2211(3) 0.0451(5) Uani 1 1 d . . . C8 C 0.89620(16) 0.93426(12) 0.8006(3) 0.0471(5) Uani 1 1 d . . . H8A H 0.9601 0.9557 0.7783 0.057 Uiso 1 1 calc R . . H8B H 0.8921 0.9534 0.9162 0.057 Uiso 1 1 calc R . . C7 C 0.86910(14) 0.64399(12) 0.7585(2) 0.0397(4) Uani 1 1 d . . . C16 C 0.66319(14) 0.48331(12) 0.4837(3) 0.0415(4) Uani 1 1 d . . . C15 C 0.50664(16) 0.44629(13) 0.2822(3) 0.0493(5) Uani 1 1 d . . . H15 H 0.4964 0.5088 0.2629 0.059 Uiso 1 1 calc R . . C17 C 0.63014(16) 0.13615(14) 0.4612(3) 0.0534(5) Uani 1 1 d . . . H17A H 0.6895 0.1548 0.4221 0.080 Uiso 1 1 calc R . . H17B H 0.6260 0.0705 0.4606 0.080 Uiso 1 1 calc R . . H17C H 0.6344 0.1584 0.5767 0.080 Uiso 1 1 calc R . . C9 C 0.80992(18) 0.97181(14) 0.6709(3) 0.0557(5) Uani 1 1 d . . . H9A H 0.8168 0.9551 0.5568 0.083 Uiso 1 1 calc R . . H9B H 0.8094 1.0373 0.6806 0.083 Uiso 1 1 calc R . . H9C H 0.7474 0.9475 0.6908 0.083 Uiso 1 1 calc R . . C14 C 0.43735(16) 0.38565(13) 0.1955(3) 0.0540(6) Uani 1 1 d . . . H14 H 0.3795 0.4067 0.1183 0.065 Uiso 1 1 calc R . . H2 H 0.7408(19) 0.6598(18) 0.602(4) 0.070(8) Uiso 1 1 d . . . H1 H 0.7896(17) 0.7488(16) 0.671(3) 0.053(6) Uiso 1 1 d . . . H10 H 0.405(2) 0.178(2) 0.158(4) 0.092(10) Uiso 1 1 d . . . H7 H 0.782(2) 0.498(2) 0.648(4) 0.086(9) 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 O5 0.0507(8) 0.0341(8) 0.0764(11) -0.0088(7) -0.0121(8) -0.0014(6) O1 0.0505(8) 0.0286(6) 0.0532(8) -0.0006(5) 0.0001(6) 0.0008(5) O6 0.0543(8) 0.0288(6) 0.0568(9) 0.0004(6) -0.0061(7) 0.0001(6) O3 0.0533(8) 0.0291(7) 0.0626(9) 0.0008(6) -0.0040(7) 0.0001(6) O4 0.0563(9) 0.0323(7) 0.0651(10) 0.0044(6) -0.0137(7) -0.0035(6) O2 0.0540(8) 0.0314(7) 0.0667(10) -0.0021(6) -0.0049(7) -0.0035(6) C1 0.0386(9) 0.0336(9) 0.0400(9) -0.0026(7) 0.0095(7) -0.0014(7) C2 0.0393(9) 0.0338(9) 0.0443(10) -0.0011(7) 0.0077(8) 0.0006(7) C12 0.0445(10) 0.0293(8) 0.0453(10) -0.0014(7) 0.0067(8) 0.0004(7) C11 0.0437(10) 0.0334(9) 0.0422(10) 0.0009(7) 0.0029(7) -0.0012(7) C3 0.0506(11) 0.0372(10) 0.0514(11) -0.0064(8) 0.0061(9) -0.0043(8) N1 0.0455(10) 0.0339(9) 0.0746(13) -0.0035(8) -0.0075(9) -0.0001(7) C6 0.0446(10) 0.0329(9) 0.0497(11) 0.0024(8) 0.0100(8) 0.0007(7) C10 0.0417(9) 0.0303(9) 0.0465(10) -0.0020(7) 0.0049(8) -0.0009(7) C4 0.0454(11) 0.0509(12) 0.0478(11) -0.0066(9) 0.0016(9) -0.0055(9) C5 0.0449(10) 0.0459(11) 0.0512(11) 0.0025(9) 0.0035(8) 0.0039(8) C13 0.0432(10) 0.0347(9) 0.0523(11) -0.0050(8) -0.0006(8) -0.0010(8) C8 0.0559(12) 0.0304(9) 0.0529(11) 0.0007(8) 0.0076(9) -0.0002(8) C7 0.0397(9) 0.0345(9) 0.0445(10) -0.0019(7) 0.0083(7) -0.0028(7) C16 0.0420(10) 0.0320(9) 0.0473(10) -0.0029(7) 0.0033(8) 0.0008(7) C15 0.0488(11) 0.0297(9) 0.0624(13) -0.0018(8) -0.0029(9) 0.0056(8) C17 0.0544(12) 0.0328(10) 0.0655(14) 0.0015(9) -0.0028(10) 0.0045(8) C9 0.0645(13) 0.0399(11) 0.0613(13) 0.0057(9) 0.0113(11) 0.0074(10) C14 0.0486(11) 0.0351(10) 0.0682(14) -0.0035(9) -0.0085(10) 0.0050(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 O5 C13 1.357(2) . ? O5 H10 0.93(3) . ? O1 C2 1.366(2) . ? O1 C8 1.442(2) . ? O6 C12 1.372(2) . ? O6 C17 1.425(2) . ? O3 C16 1.222(2) . ? O4 C16 1.325(2) . ? O4 H7 0.97(3) . ? O2 C7 1.257(2) . ? C1 C6 1.388(3) . ? C1 C2 1.409(3) . ? C1 C7 1.495(2) . ? C2 C3 1.395(3) . ? C12 C11 1.384(3) . ? C12 C13 1.404(3) . ? C11 C10 1.401(3) . ? C11 H11 0.9500 . ? C3 C4 1.383(3) . ? C3 H3 0.9500 . ? N1 C7 1.317(3) . ? N1 H2 0.91(3) . ? N1 H1 0.90(2) . ? C6 C5 1.384(3) . ? C6 H6 0.9500 . ? C10 C15 1.386(3) . ? C10 C16 1.472(3) . ? C4 C5 1.380(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C13 C14 1.382(3) . ? C8 C9 1.507(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C15 C14 1.386(3) . ? C15 H15 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C14 H14 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 C13 O5 H10 110(2) . . ? C2 O1 C8 118.94(15) . . ? C12 O6 C17 117.05(15) . . ? C16 O4 H7 108.8(18) . . ? C6 C1 C2 118.13(17) . . ? C6 C1 C7 116.67(16) . . ? C2 C1 C7 125.20(16) . . ? O1 C2 C3 122.68(17) . . ? O1 C2 C1 117.91(16) . . ? C3 C2 C1 119.40(17) . . ? O6 C12 C11 125.80(17) . . ? O6 C12 C13 114.14(16) . . ? C11 C12 C13 120.07(17) . . ? C12 C11 C10 119.88(17) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C4 C3 C2 120.72(18) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C7 N1 H2 121.0(17) . . ? C7 N1 H1 122.1(15) . . ? H2 N1 H1 116(2) . . ? C5 C6 C1 122.47(18) . . ? C5 C6 H6 118.8 . . ? C1 C6 H6 118.8 . . ? C15 C10 C11 119.60(17) . . ? C15 C10 C16 118.62(17) . . ? C11 C10 C16 121.77(17) . . ? C5 C4 C3 120.52(19) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 118.75(19) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? O5 C13 C14 118.74(18) . . ? O5 C13 C12 121.53(17) . . ? C14 C13 C12 119.73(17) . . ? O1 C8 C9 106.79(16) . . ? O1 C8 H8A 110.4 . . ? C9 C8 H8A 110.4 . . ? O1 C8 H8B 110.4 . . ? C9 C8 H8B 110.4 . . ? H8A C8 H8B 108.6 . . ? O2 C7 N1 120.89(18) . . ? O2 C7 C1 118.91(17) . . ? N1 C7 C1 120.20(17) . . ? O3 C16 O4 122.11(17) . . ? O3 C16 C10 123.20(17) . . ? O4 C16 C10 114.69(16) . . ? C10 C15 C14 120.55(18) . . ? C10 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? O6 C17 H17A 109.5 . . ? O6 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O6 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C13 C14 C15 120.15(19) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.268 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.050 data_EA+ABA _database_code_depnum_ccdc_archive 'CCDC 752483' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2:1 ethenzamide and 4-aminobenzoic acid cocrystal ; _chemical_name_common '2:1 ethenzamide and 4-aminobenzoic acid cocrystal' _chemical_melting_point ? _chemical_formula_moiety '2(C9 H11 N O2), C7 H7 N O2' _chemical_formula_sum 'C25 H29 N3 O6' _chemical_formula_weight 467.51 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' 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 P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.0570(18) _cell_length_b 32.685(7) _cell_length_c 8.1857(16) _cell_angle_alpha 90.00 _cell_angle_beta 93.39(3) _cell_angle_gamma 90.00 _cell_volume 2419.0(9) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 4765 _cell_measurement_theta_min 2.4926 _cell_measurement_theta_max 31.0723 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'CCD area deterctor' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20924 _diffrn_reflns_av_R_equivalents 0.0431 _diffrn_reflns_av_sigmaI/netI 0.0549 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -46 _diffrn_reflns_limit_k_max 46 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.25 _diffrn_reflns_theta_max 30.50 _reflns_number_total 6984 _reflns_number_gt 5267 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.0652P)^2^+0.8594P] 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 6984 _refine_ls_number_parameters 337 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1159 _refine_ls_R_factor_gt 0.0864 _refine_ls_wR_factor_ref 0.1969 _refine_ls_wR_factor_gt 0.1790 _refine_ls_goodness_of_fit_ref 1.192 _refine_ls_restrained_S_all 1.192 _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 O1A O 1.08746(16) 0.01441(4) 0.32872(19) 0.0311(4) Uani 1 1 d . . . O2A O 0.75636(17) 0.08228(5) 0.08962(19) 0.0333(4) Uani 1 1 d . . . O1 O 0.63967(16) 0.24577(5) -0.0023(2) 0.0335(4) Uani 1 1 d . . . O3 O 0.47503(17) 0.12516(5) 0.90681(19) 0.0337(4) Uani 1 1 d . . . O2 O 0.96511(16) 0.17162(5) 0.2130(2) 0.0342(4) Uani 1 1 d . . . C1 C 0.8639(2) 0.23720(6) 0.1566(3) 0.0267(4) Uani 1 1 d . . . N1 N 0.7400(2) 0.17261(6) 0.0872(2) 0.0315(4) Uani 1 1 d . . . C1A C 0.8687(2) 0.01828(6) 0.1586(3) 0.0282(4) Uani 1 1 d . . . C10 C 0.4605(2) 0.12030(6) 0.6171(3) 0.0257(4) Uani 1 1 d . . . N1A N 0.9546(2) 0.08478(6) 0.2632(3) 0.0343(5) Uani 1 1 d . . . O4 O 0.64894(18) 0.08998(5) 0.7849(2) 0.0359(4) Uani 1 1 d . . . C2A C 0.9826(2) -0.00537(6) 0.2338(3) 0.0286(4) Uani 1 1 d . . . C15 C 0.5311(2) 0.11032(6) 0.4747(3) 0.0262(4) Uani 1 1 d . . . H15 H 0.6237 0.0966 0.4839 0.031 Uiso 1 1 calc R . . C8A C 1.2074(2) -0.00858(7) 0.4056(3) 0.0310(5) Uani 1 1 d . . . H8AA H 1.2625 -0.0232 0.3224 0.037 Uiso 1 1 calc R . . H8AB H 1.1696 -0.0290 0.4823 0.037 Uiso 1 1 calc R . . C2 C 0.7591(2) 0.26331(7) 0.0784(3) 0.0287(4) Uani 1 1 d . . . C12 C 0.2581(2) 0.14864(6) 0.4492(3) 0.0285(4) Uani 1 1 d . . . H12 H 0.1633 0.1611 0.4407 0.034 Uiso 1 1 calc R . . N3 N 0.2736(2) 0.15121(7) 0.1561(3) 0.0353(5) Uani 1 1 d . . . C16 C 0.5254(2) 0.11237(6) 0.7815(3) 0.0282(4) Uani 1 1 d . . . C7 C 0.8583(2) 0.19151(6) 0.1526(3) 0.0272(4) Uani 1 1 d . . . C14 C 0.4697(2) 0.11985(6) 0.3222(3) 0.0281(4) Uani 1 1 d . . . H14 H 0.5201 0.1129 0.2275 0.034 Uiso 1 1 calc R . . C13 C 0.3319(2) 0.13985(6) 0.3062(3) 0.0269(4) Uani 1 1 d . . . C7A C 0.8581(2) 0.06401(6) 0.1689(3) 0.0278(4) Uani 1 1 d . . . C6A C 0.7584(3) -0.00161(7) 0.0640(3) 0.0345(5) Uani 1 1 d . . . H6A H 0.6799 0.0140 0.0134 0.041 Uiso 1 1 calc R . . C11 C 0.3225(2) 0.13924(6) 0.6002(3) 0.0275(4) Uani 1 1 d . . . H11 H 0.2721 0.1458 0.6954 0.033 Uiso 1 1 calc R . . C3 C 0.7793(3) 0.30554(7) 0.0856(3) 0.0366(5) Uani 1 1 d . . . H3 H 0.7100 0.3232 0.0296 0.044 Uiso 1 1 calc R . . C8 C 0.5310(2) 0.27130(7) -0.0857(3) 0.0339(5) Uani 1 1 d . . . H8B H 0.5743 0.2858 -0.1775 0.041 Uiso 1 1 calc R . . H8A H 0.4931 0.2918 -0.0097 0.041 Uiso 1 1 calc R . . C6 C 0.9834(2) 0.25462(7) 0.2444(3) 0.0321(5) Uani 1 1 d . . . H6 H 1.0548 0.2373 0.2985 0.039 Uiso 1 1 calc R . . C3A C 0.9843(3) -0.04766(7) 0.2103(3) 0.0333(5) Uani 1 1 d . . . H3A H 1.0618 -0.0636 0.2609 0.040 Uiso 1 1 calc R . . C5A C 0.7598(3) -0.04357(7) 0.0413(3) 0.0392(6) Uani 1 1 d . . . H5A H 0.6831 -0.0566 -0.0235 0.047 Uiso 1 1 calc R . . C4 C 0.9000(3) 0.32180(7) 0.1741(3) 0.0408(6) Uani 1 1 d . . . H4 H 0.9133 0.3506 0.1790 0.049 Uiso 1 1 calc R . . C9A C 1.3055(2) 0.02165(7) 0.4959(3) 0.0375(5) Uani 1 1 d . . . H9AA H 1.3491 0.0401 0.4176 0.056 Uiso 1 1 calc R . . H9AB H 1.3845 0.0071 0.5590 0.056 Uiso 1 1 calc R . . H9AC H 1.2473 0.0376 0.5705 0.056 Uiso 1 1 calc R . . C4A C 0.8745(3) -0.06623(7) 0.1146(3) 0.0396(6) Uani 1 1 d . . . H4A H 0.8772 -0.0950 0.0984 0.047 Uiso 1 1 calc R . . C5 C 1.0015(3) 0.29640(7) 0.2555(3) 0.0386(5) Uani 1 1 d . . . H5 H 1.0831 0.3076 0.3186 0.046 Uiso 1 1 calc R . . C9 C 0.4090(3) 0.24364(8) -0.1482(3) 0.0420(6) Uani 1 1 d . . . H9A H 0.4495 0.2223 -0.2167 0.063 Uiso 1 1 calc R . . H9B H 0.3351 0.2595 -0.2133 0.063 Uiso 1 1 calc R . . H9C H 0.3626 0.2310 -0.0556 0.063 Uiso 1 1 calc R . . H1A H 1.035(3) 0.0708(8) 0.316(3) 0.045(7) Uiso 1 1 d . . . H16 H 0.321(3) 0.1445(9) 0.063(4) 0.051(8) Uiso 1 1 d . . . H13 H 0.186(3) 0.1614(8) 0.152(3) 0.038(7) Uiso 1 1 d . . . H2 H 0.743(3) 0.1432(9) 0.086(3) 0.039(7) Uiso 1 1 d . . . H1 H 0.666(3) 0.1872(9) 0.030(4) 0.052(8) Uiso 1 1 d . . . H2A H 0.955(3) 0.1118(10) 0.264(4) 0.051(8) Uiso 1 1 d . . . H10 H 0.685(4) 0.0856(11) 0.897(5) 0.083(12) 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 O1A 0.0337(8) 0.0231(7) 0.0358(9) -0.0013(6) -0.0045(6) 0.0024(6) O2A 0.0359(8) 0.0312(8) 0.0318(9) 0.0006(6) -0.0069(7) 0.0057(6) O1 0.0299(7) 0.0278(8) 0.0417(10) 0.0045(7) -0.0059(7) 0.0051(6) O3 0.0349(8) 0.0399(9) 0.0260(8) -0.0025(7) 0.0006(6) 0.0064(7) O2 0.0294(7) 0.0268(8) 0.0455(10) 0.0014(7) -0.0058(7) 0.0035(6) C1 0.0267(9) 0.0266(10) 0.0273(11) 0.0015(8) 0.0044(8) 0.0003(8) N1 0.0277(9) 0.0247(9) 0.0414(12) 0.0004(8) -0.0047(8) 0.0028(7) C1A 0.0339(10) 0.0258(10) 0.0249(11) 0.0003(8) 0.0023(8) -0.0026(8) C10 0.0252(9) 0.0226(9) 0.0291(11) -0.0014(8) -0.0007(8) 0.0000(7) N1A 0.0375(10) 0.0230(9) 0.0409(12) 0.0016(8) -0.0115(9) 0.0022(8) O4 0.0366(8) 0.0405(9) 0.0299(9) -0.0032(7) -0.0035(7) 0.0134(7) C2A 0.0333(10) 0.0274(10) 0.0252(11) 0.0001(8) 0.0031(8) -0.0017(8) C15 0.0244(9) 0.0246(10) 0.0295(11) -0.0005(8) 0.0015(8) 0.0004(8) C8A 0.0326(10) 0.0279(10) 0.0325(12) 0.0024(9) 0.0024(9) 0.0078(9) C2 0.0273(9) 0.0295(10) 0.0294(11) 0.0019(9) 0.0032(8) 0.0008(8) C12 0.0233(9) 0.0295(10) 0.0326(12) -0.0011(9) 0.0006(8) 0.0002(8) N3 0.0311(9) 0.0471(12) 0.0275(11) 0.0013(9) -0.0011(8) 0.0063(9) C16 0.0273(10) 0.0252(10) 0.0318(12) -0.0009(9) 0.0007(8) -0.0006(8) C7 0.0245(9) 0.0277(10) 0.0293(11) 0.0017(8) -0.0002(8) 0.0034(8) C14 0.0283(10) 0.0277(10) 0.0283(11) -0.0031(8) 0.0026(8) -0.0016(8) C13 0.0268(9) 0.0268(10) 0.0268(11) 0.0003(8) -0.0019(8) -0.0012(8) C7A 0.0314(10) 0.0274(10) 0.0244(11) 0.0025(8) 0.0004(8) 0.0017(8) C6A 0.0405(12) 0.0326(11) 0.0300(12) 0.0020(9) -0.0007(9) -0.0061(10) C11 0.0282(9) 0.0284(10) 0.0261(11) -0.0015(8) 0.0033(8) 0.0001(8) C3 0.0377(11) 0.0279(11) 0.0447(14) 0.0058(10) 0.0071(10) 0.0044(9) C8 0.0318(11) 0.0344(12) 0.0354(13) 0.0065(10) 0.0002(9) 0.0094(9) C6 0.0285(10) 0.0292(11) 0.0386(13) 0.0011(9) 0.0025(9) -0.0012(8) C3A 0.0423(12) 0.0241(10) 0.0339(12) 0.0011(9) 0.0049(9) -0.0003(9) C5A 0.0491(13) 0.0359(12) 0.0321(13) -0.0017(10) -0.0022(10) -0.0144(11) C4 0.0432(13) 0.0261(11) 0.0535(16) -0.0003(11) 0.0071(11) -0.0046(10) C9A 0.0303(11) 0.0367(12) 0.0453(15) 0.0027(11) 0.0010(10) 0.0018(9) C4A 0.0556(15) 0.0263(11) 0.0373(14) -0.0014(10) 0.0072(11) -0.0078(11) C5 0.0377(12) 0.0338(12) 0.0444(14) -0.0023(10) 0.0019(10) -0.0058(10) C9 0.0365(12) 0.0471(14) 0.0415(15) 0.0049(11) -0.0059(10) 0.0074(11) _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 O1A C2A 1.355(3) . ? O1A C8A 1.435(2) . ? O2A C7A 1.247(2) . ? O1 C2 1.360(3) . ? O1 C8 1.432(2) . ? O3 C16 1.221(3) . ? O2 C7 1.244(2) . ? C1 C6 1.386(3) . ? C1 C2 1.402(3) . ? C1 C7 1.494(3) . ? N1 C7 1.322(3) . ? N1 H2 0.96(3) . ? N1 H1 0.93(3) . ? C1A C6A 1.389(3) . ? C1A C2A 1.402(3) . ? C1A C7A 1.501(3) . ? C10 C11 1.394(3) . ? C10 C15 1.401(3) . ? C10 C16 1.460(3) . ? N1A C7A 1.320(3) . ? N1A H1A 0.94(3) . ? N1A H2A 0.88(3) . ? O4 C16 1.336(2) . ? O4 H10 0.97(4) . ? C2A C3A 1.396(3) . ? C15 C14 1.372(3) . ? C15 H15 0.9500 . ? C8A C9A 1.495(3) . ? C8A H8AA 0.9900 . ? C8A H8AB 0.9900 . ? C2 C3 1.393(3) . ? C12 C11 1.370(3) . ? C12 C13 1.411(3) . ? C12 H12 0.9500 . ? N3 C13 1.360(3) . ? N3 H16 0.92(3) . ? N3 H13 0.86(3) . ? C14 C13 1.408(3) . ? C14 H14 0.9500 . ? C6A C5A 1.384(3) . ? C6A H6A 0.9500 . ? C11 H11 0.9500 . ? C3 C4 1.382(3) . ? C3 H3 0.9500 . ? C8 C9 1.494(3) . ? C8 H8B 0.9900 . ? C8 H8A 0.9900 . ? C6 C5 1.378(3) . ? C6 H6 0.9500 . ? C3A C4A 1.371(3) . ? C3A H3A 0.9500 . ? C5A C4A 1.383(4) . ? C5A H5A 0.9500 . ? C4 C5 1.380(3) . ? C4 H4 0.9500 . ? C9A H9AA 0.9800 . ? C9A H9AB 0.9800 . ? C9A H9AC 0.9800 . ? C4A H4A 0.9500 . ? C5 H5 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? 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 C2A O1A C8A 119.22(16) . . ? C2 O1 C8 119.35(17) . . ? C6 C1 C2 118.3(2) . . ? C6 C1 C7 116.52(18) . . ? C2 C1 C7 125.22(19) . . ? C7 N1 H2 116.6(15) . . ? C7 N1 H1 120.6(18) . . ? H2 N1 H1 122(2) . . ? C6A C1A C2A 118.2(2) . . ? C6A C1A C7A 116.83(19) . . ? C2A C1A C7A 124.91(19) . . ? C11 C10 C15 118.10(19) . . ? C11 C10 C16 118.69(19) . . ? C15 C10 C16 123.21(18) . . ? C7A N1A H1A 119.1(16) . . ? C7A N1A H2A 121.1(19) . . ? H1A N1A H2A 119(2) . . ? C16 O4 H10 110(2) . . ? O1A C2A C3A 122.59(19) . . ? O1A C2A C1A 117.48(18) . . ? C3A C2A C1A 119.9(2) . . ? C14 C15 C10 121.62(19) . . ? C14 C15 H15 119.2 . . ? C10 C15 H15 119.2 . . ? O1A C8A C9A 106.45(17) . . ? O1A C8A H8AA 110.4 . . ? C9A C8A H8AA 110.4 . . ? O1A C8A H8AB 110.4 . . ? C9A C8A H8AB 110.4 . . ? H8AA C8A H8AB 108.6 . . ? O1 C2 C3 122.46(19) . . ? O1 C2 C1 117.54(19) . . ? C3 C2 C1 120.0(2) . . ? C11 C12 C13 120.37(19) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C13 N3 H16 120.4(18) . . ? C13 N3 H13 116.9(18) . . ? H16 N3 H13 122(2) . . ? O3 C16 O4 121.6(2) . . ? O3 C16 C10 124.30(19) . . ? O4 C16 C10 114.04(19) . . ? O2 C7 N1 120.6(2) . . ? O2 C7 C1 119.27(18) . . ? N1 C7 C1 120.10(18) . . ? C15 C14 C13 120.0(2) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? N3 C13 C14 120.4(2) . . ? N3 C13 C12 121.07(19) . . ? C14 C13 C12 118.54(19) . . ? O2A C7A N1A 120.1(2) . . ? O2A C7A C1A 119.69(19) . . ? N1A C7A C1A 120.18(18) . . ? C5A C6A C1A 121.8(2) . . ? C5A C6A H6A 119.1 . . ? C1A C6A H6A 119.1 . . ? C12 C11 C10 121.3(2) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C4 C3 C2 120.1(2) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? O1 C8 C9 106.49(18) . . ? O1 C8 H8B 110.4 . . ? C9 C8 H8B 110.4 . . ? O1 C8 H8A 110.4 . . ? C9 C8 H8A 110.4 . . ? H8B C8 H8A 108.6 . . ? C5 C6 C1 121.9(2) . . ? C5 C6 H6 119.1 . . ? C1 C6 H6 119.1 . . ? C4A C3A C2A 120.3(2) . . ? C4A C3A H3A 119.9 . . ? C2A C3A H3A 119.9 . . ? C4A C5A C6A 119.0(2) . . ? C4A C5A H5A 120.5 . . ? C6A C5A H5A 120.5 . . ? C5 C4 C3 120.4(2) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C8A C9A H9AA 109.5 . . ? C8A C9A H9AB 109.5 . . ? H9AA C9A H9AB 109.5 . . ? C8A C9A H9AC 109.5 . . ? H9AA C9A H9AC 109.5 . . ? H9AB C9A H9AC 109.5 . . ? C3A C4A C5A 120.8(2) . . ? C3A C4A H4A 119.6 . . ? C5A C4A H4A 119.6 . . ? C6 C5 C4 119.4(2) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.258 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.057 data_EA+HBA _database_code_depnum_ccdc_archive 'CCDC 752484' _audit_creation_method SHELXL-97 _chemical_name_systematic ; cocrystal of ethenzamide with 4-hydroxybenzoic acid ; _chemical_name_common '1:1 ethenzamide and 4-hydroxybenzoic acid' _chemical_melting_point ? _chemical_formula_moiety 'C9 H11 N O2, C7 H6 O3' _chemical_formula_sum 'C16 H17 N O5' _chemical_formula_weight 303.31 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' 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 _symmetry_space_group_name_Hall '-P 2yn' 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 9.4871(19) _cell_length_b 6.4682(13) _cell_length_c 23.703(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.65(3) _cell_angle_gamma 90.00 _cell_volume 1438.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 3357 _cell_measurement_theta_min 2.2141 _cell_measurement_theta_max 31.0775 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.964 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10543 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 28.27 _reflns_number_total 3571 _reflns_number_gt 3148 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.0691P)^2^+0.5924P] 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 3571 _refine_ls_number_parameters 216 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0683 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1550 _refine_ls_wR_factor_gt 0.1481 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.123 _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 O5 O -0.04242(13) 0.85065(19) 0.05951(5) 0.0268(3) Uani 1 1 d . . . O4 O 0.12327(13) 0.81841(19) 0.00162(5) 0.0274(3) Uani 1 1 d . . . O3 O 0.23897(13) -0.00406(18) 0.14468(5) 0.0260(3) Uani 1 1 d . . . C10 C 0.10793(17) 0.5576(2) 0.07055(7) 0.0217(3) Uani 1 1 d . . . C13 C 0.19310(17) 0.1804(2) 0.12190(7) 0.0218(3) Uani 1 1 d . . . C16 C 0.06390(17) 0.7532(2) 0.04139(7) 0.0224(3) Uani 1 1 d . . . C12 C 0.09168(17) 0.3013(3) 0.14356(7) 0.0235(3) Uani 1 1 d . . . H12 H 0.0523 0.2564 0.1750 0.028 Uiso 1 1 calc R . . C11 C 0.04991(17) 0.4887(3) 0.11792(7) 0.0231(3) Uani 1 1 d . . . H11 H -0.0175 0.5693 0.1324 0.028 Uiso 1 1 calc R . . C14 C 0.25180(18) 0.2485(3) 0.07479(7) 0.0246(3) Uani 1 1 d . . . H14 H 0.3196 0.1685 0.0604 0.030 Uiso 1 1 calc R . . C15 C 0.20908(18) 0.4351(3) 0.04954(7) 0.0241(3) Uani 1 1 d . . . H15 H 0.2484 0.4797 0.0180 0.029 Uiso 1 1 calc R . . O1 O 0.55635(13) 0.54711(18) 0.13114(5) 0.0260(3) Uani 1 1 d . . . C1 C 0.52908(16) 0.2959(2) 0.20155(7) 0.0206(3) Uani 1 1 d . . . O2 O 0.36600(13) 0.33917(18) 0.26731(5) 0.0276(3) Uani 1 1 d . . . N1 N 0.37695(16) 0.5999(2) 0.20565(6) 0.0260(3) Uani 1 1 d . . . C2 C 0.59911(17) 0.3632(2) 0.15653(7) 0.0219(3) Uani 1 1 d . . . C3 C 0.70827(18) 0.2439(3) 0.13979(8) 0.0266(4) Uani 1 1 d . . . H3 H 0.7559 0.2895 0.1106 0.032 Uiso 1 1 calc R . . C5 C 0.67393(18) -0.0153(3) 0.20957(8) 0.0277(4) Uani 1 1 d . . . H5 H 0.6972 -0.1429 0.2265 0.033 Uiso 1 1 calc R . . C7 C 0.41752(17) 0.4153(3) 0.22623(7) 0.0217(3) Uani 1 1 d . . . C6 C 0.56731(18) 0.1045(3) 0.22678(7) 0.0242(3) Uani 1 1 d . . . H6 H 0.5199 0.0566 0.2558 0.029 Uiso 1 1 calc R . . C8 C 0.6076(2) 0.6034(3) 0.07932(7) 0.0294(4) Uani 1 1 d . . . H8A H 0.5928 0.4909 0.0520 0.035 Uiso 1 1 calc R . . H8B H 0.7087 0.6343 0.0869 0.035 Uiso 1 1 calc R . . C4 C 0.74563(18) 0.0574(3) 0.16679(8) 0.0296(4) Uani 1 1 d . . . H4 H 0.8198 -0.0200 0.1560 0.036 Uiso 1 1 calc R . . C9 C 0.5251(2) 0.7915(3) 0.05607(8) 0.0335(4) Uani 1 1 d . . . H9A H 0.4259 0.7568 0.0467 0.050 Uiso 1 1 calc R . . H9B H 0.5603 0.8385 0.0224 0.050 Uiso 1 1 calc R . . H9C H 0.5363 0.8990 0.0843 0.050 Uiso 1 1 calc R . . H2 H 0.302(3) 0.663(3) 0.2183(10) 0.041(6) Uiso 1 1 d . . . H1 H 0.412(2) 0.651(3) 0.1741(10) 0.037(6) Uiso 1 1 d . . . H3A H 0.198(3) -0.036(4) 0.1766(12) 0.061(8) Uiso 1 1 d . . . H5A H -0.066(3) 0.975(5) 0.0360(13) 0.078(9) 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 O5 0.0278(6) 0.0245(6) 0.0283(6) 0.0016(5) 0.0049(5) 0.0040(5) O4 0.0299(6) 0.0252(6) 0.0277(6) 0.0048(5) 0.0063(5) 0.0007(5) O3 0.0299(6) 0.0221(6) 0.0273(6) 0.0051(5) 0.0081(5) 0.0041(5) C10 0.0233(7) 0.0202(8) 0.0209(7) -0.0003(6) 0.0007(6) -0.0022(6) C13 0.0229(7) 0.0189(7) 0.0231(7) 0.0000(6) 0.0017(6) -0.0018(6) C16 0.0228(7) 0.0213(8) 0.0228(8) -0.0017(6) 0.0021(6) -0.0013(6) C12 0.0238(8) 0.0250(8) 0.0222(8) 0.0021(6) 0.0050(6) -0.0009(6) C11 0.0217(7) 0.0232(8) 0.0246(8) -0.0013(6) 0.0039(6) 0.0012(6) C14 0.0245(8) 0.0235(8) 0.0266(8) -0.0008(6) 0.0064(6) 0.0011(6) C15 0.0263(8) 0.0237(8) 0.0231(8) 0.0007(6) 0.0064(6) -0.0026(6) O1 0.0311(6) 0.0233(6) 0.0258(6) 0.0040(5) 0.0111(5) 0.0031(5) C1 0.0185(7) 0.0208(7) 0.0220(7) -0.0024(6) 0.0010(6) -0.0015(6) O2 0.0326(6) 0.0244(6) 0.0281(6) 0.0004(5) 0.0124(5) -0.0030(5) N1 0.0272(7) 0.0248(7) 0.0276(7) 0.0031(6) 0.0091(6) 0.0047(6) C2 0.0214(7) 0.0219(8) 0.0222(7) -0.0008(6) 0.0027(6) -0.0009(6) C3 0.0228(8) 0.0288(9) 0.0293(8) -0.0036(7) 0.0076(6) -0.0005(6) C5 0.0269(8) 0.0217(8) 0.0322(9) -0.0021(7) -0.0028(7) 0.0015(6) C7 0.0213(7) 0.0223(8) 0.0217(7) -0.0006(6) 0.0040(6) -0.0027(6) C6 0.0251(8) 0.0225(8) 0.0247(8) -0.0004(6) 0.0027(6) -0.0027(6) C8 0.0313(9) 0.0331(9) 0.0258(8) 0.0045(7) 0.0111(7) 0.0004(7) C4 0.0222(8) 0.0275(9) 0.0386(10) -0.0056(7) 0.0031(7) 0.0034(6) C9 0.0395(10) 0.0326(10) 0.0291(9) 0.0054(7) 0.0075(8) -0.0022(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 O5 C16 1.315(2) . ? O5 H5A 0.99(3) . ? O4 C16 1.242(2) . ? O3 C13 1.3543(19) . ? O3 H3A 0.92(3) . ? C10 C15 1.393(2) . ? C10 C11 1.396(2) . ? C10 C16 1.472(2) . ? C13 C14 1.392(2) . ? C13 C12 1.396(2) . ? C12 C11 1.387(2) . ? C12 H12 0.9300 . ? C11 H11 0.9300 . ? C14 C15 1.381(2) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O1 C2 1.3669(19) . ? O1 C8 1.434(2) . ? C1 C6 1.399(2) . ? C1 C2 1.408(2) . ? C1 C7 1.498(2) . ? O2 C7 1.2539(19) . ? N1 C7 1.325(2) . ? N1 H2 0.91(2) . ? N1 H1 0.92(2) . ? C2 C3 1.396(2) . ? C3 C4 1.387(3) . ? C3 H3 0.9300 . ? C5 C6 1.384(2) . ? C5 C4 1.385(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C8 C9 1.505(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C4 H4 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 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 C16 O5 H5A 109.1(17) . . ? C13 O3 H3A 112.2(17) . . ? C15 C10 C11 118.85(15) . . ? C15 C10 C16 118.89(14) . . ? C11 C10 C16 122.26(15) . . ? O3 C13 C14 117.07(14) . . ? O3 C13 C12 123.01(14) . . ? C14 C13 C12 119.91(15) . . ? O4 C16 O5 122.88(15) . . ? O4 C16 C10 121.26(15) . . ? O5 C16 C10 115.85(14) . . ? C11 C12 C13 119.72(15) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C11 C10 120.68(15) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C15 C14 C13 119.83(15) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C10 121.01(15) . . ? C14 C15 H15 119.5 . . ? C10 C15 H15 119.5 . . ? C2 O1 C8 118.80(13) . . ? C6 C1 C2 118.43(14) . . ? C6 C1 C7 116.24(14) . . ? C2 C1 C7 125.32(14) . . ? C7 N1 H2 118.8(14) . . ? C7 N1 H1 120.0(14) . . ? H2 N1 H1 120.2(19) . . ? O1 C2 C3 122.65(15) . . ? O1 C2 C1 117.40(14) . . ? C3 C2 C1 119.95(15) . . ? C4 C3 C2 119.92(16) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C6 C5 C4 119.16(16) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? O2 C7 N1 120.95(15) . . ? O2 C7 C1 118.78(15) . . ? N1 C7 C1 120.25(14) . . ? C5 C6 C1 121.57(15) . . ? C5 C6 H6 119.2 . . ? C1 C6 H6 119.2 . . ? O1 C8 C9 107.11(14) . . ? O1 C8 H8A 110.3 . . ? C9 C8 H8A 110.3 . . ? O1 C8 H8B 110.3 . . ? C9 C8 H8B 110.3 . . ? H8A C8 H8B 108.5 . . ? C5 C4 C3 120.89(16) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.278 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.058 #====END data_eafa _database_code_depnum_ccdc_archive 'CCDC 896104' #TrackingRef 'EAFA.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'cocrystal of ethenzamide with fumaric acid' ; _chemical_name_common '1:0.5 ethenzamide and fumaric acid cocrystal' _chemical_melting_point ? _chemical_formula_moiety 'C9 H11 N O2, 0.5(C4 H4 O4)' _chemical_formula_sum 'C11 H13 N O4' _chemical_formula_weight 223.22 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' 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 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' _cell_length_a 8.2154(16) _cell_length_b 8.4654(17) _cell_length_c 9.3991(19) _cell_angle_alpha 70.30(3) _cell_angle_beta 71.82(3) _cell_angle_gamma 65.97(3) _cell_volume 550.36(19) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 1457 _cell_measurement_theta_min 2.3505 _cell_measurement_theta_max 30.8782 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 236 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.981 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7818 _diffrn_reflns_av_R_equivalents 0.0422 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2692 _reflns_number_gt 2442 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.0921P)^2^+0.2446P] 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 2692 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0827 _refine_ls_R_factor_gt 0.0763 _refine_ls_wR_factor_ref 0.1960 _refine_ls_wR_factor_gt 0.1899 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.154 _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 1.17765(18) 0.25086(19) 0.67818(16) 0.0303(4) Uani 1 1 d . . . O2 O 0.78405(19) 0.31846(19) 0.45284(17) 0.0327(4) Uani 1 1 d . . . N1 N 1.0774(2) 0.1775(2) 0.4713(2) 0.0306(4) Uani 1 1 d . . . C1 C 0.8725(3) 0.3716(2) 0.6442(2) 0.0256(4) Uani 1 1 d . . . C7 C 0.9112(3) 0.2853(3) 0.5169(2) 0.0268(4) Uani 1 1 d . . . C3 C 0.9507(3) 0.4498(3) 0.8333(2) 0.0291(4) Uani 1 1 d . . . H3 H 1.0377 0.4436 0.8809 0.035 Uiso 1 1 calc R . . C2 C 1.0028(3) 0.3579(2) 0.7200(2) 0.0261(4) Uani 1 1 d . . . C6 C 0.6911(3) 0.4752(3) 0.6892(2) 0.0293(4) Uani 1 1 d . . . H6 H 0.6037 0.4851 0.6403 0.035 Uiso 1 1 calc R . . C4 C 0.7703(3) 0.5507(3) 0.8761(2) 0.0306(4) Uani 1 1 d . . . H4 H 0.7368 0.6106 0.9530 0.037 Uiso 1 1 calc R . . C5 C 0.6389(3) 0.5634(3) 0.8051(2) 0.0319(5) Uani 1 1 d . . . H5 H 0.5175 0.6301 0.8349 0.038 Uiso 1 1 calc R . . C8 C 1.3167(3) 0.2342(3) 0.7518(3) 0.0327(5) Uani 1 1 d . . . H8A H 1.2834 0.1924 0.8628 0.039 Uiso 1 1 calc R . . H8B H 1.3320 0.3485 0.7292 0.039 Uiso 1 1 calc R . . C9 C 1.4896(3) 0.1020(3) 0.6878(3) 0.0401(5) Uani 1 1 d . . . H9A H 1.4709 -0.0088 0.7072 0.060 Uiso 1 1 calc R . . H9B H 1.5848 0.0831 0.7367 0.060 Uiso 1 1 calc R . . H9C H 1.5235 0.1474 0.5786 0.060 Uiso 1 1 calc R . . O3 O 0.20983(19) 0.7948(2) 0.76643(17) 0.0339(4) Uani 1 1 d . . . O4 O -0.0950(2) 0.9185(2) 0.80920(17) 0.0353(4) Uani 1 1 d . . . C10 C 0.0515(3) 0.8845(2) 0.8393(2) 0.0273(4) Uani 1 1 d . . . C11 C 0.0697(3) 0.9422(2) 0.9649(2) 0.0287(4) Uani 1 1 d . . . H11 H 0.1812 0.8962 0.9947 0.034 Uiso 1 1 calc R . . H1 H 1.168(4) 0.160(3) 0.515(3) 0.043(7) Uiso 1 1 d . . . H2 H 1.100(5) 0.135(5) 0.387(4) 0.075(10) Uiso 1 1 d . . . H3A H 0.197(4) 0.759(4) 0.687(4) 0.068(9) 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 O1 0.0210(7) 0.0358(7) 0.0341(8) -0.0127(6) -0.0083(6) -0.0042(6) O2 0.0267(7) 0.0403(8) 0.0342(8) -0.0159(6) -0.0087(6) -0.0070(6) N1 0.0269(9) 0.0340(9) 0.0314(9) -0.0130(7) -0.0072(7) -0.0058(7) C1 0.0268(9) 0.0247(9) 0.0240(9) -0.0042(7) -0.0051(7) -0.0091(7) C7 0.0276(9) 0.0290(9) 0.0243(9) -0.0049(7) -0.0068(7) -0.0101(7) C3 0.0272(10) 0.0329(10) 0.0283(10) -0.0069(7) -0.0091(8) -0.0093(8) C2 0.0250(9) 0.0259(9) 0.0246(9) -0.0045(7) -0.0051(7) -0.0070(7) C6 0.0278(10) 0.0326(10) 0.0287(10) -0.0080(8) -0.0066(8) -0.0102(8) C4 0.0304(10) 0.0331(10) 0.0287(10) -0.0119(8) -0.0059(8) -0.0075(8) C5 0.0263(9) 0.0343(10) 0.0320(10) -0.0103(8) -0.0058(8) -0.0054(8) C8 0.0244(9) 0.0355(10) 0.0403(11) -0.0086(8) -0.0132(8) -0.0079(8) C9 0.0274(10) 0.0430(12) 0.0503(14) -0.0135(10) -0.0113(9) -0.0081(9) O3 0.0266(7) 0.0430(8) 0.0350(8) -0.0187(6) -0.0098(6) -0.0045(6) O4 0.0275(7) 0.0443(8) 0.0384(8) -0.0171(7) -0.0104(6) -0.0078(6) C10 0.0266(9) 0.0273(9) 0.0279(9) -0.0068(7) -0.0070(7) -0.0079(7) C11 0.0285(10) 0.0301(9) 0.0282(10) -0.0048(7) -0.0099(8) -0.0095(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 O1 C2 1.366(2) . ? O1 C8 1.449(2) . ? O2 C7 1.254(2) . ? N1 C7 1.329(3) . ? N1 H1 0.89(3) . ? N1 H2 0.92(4) . ? C1 C6 1.401(3) . ? C1 C2 1.409(3) . ? C1 C7 1.493(3) . ? C3 C4 1.385(3) . ? C3 C2 1.388(3) . ? C3 H3 0.9300 . ? C6 C5 1.387(3) . ? C6 H6 0.9300 . ? C4 C5 1.389(3) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C8 C9 1.502(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? O3 C10 1.315(2) . ? O3 H3A 0.95(4) . ? O4 C10 1.219(2) . ? C10 C11 1.488(3) . ? C11 C11 1.326(4) 2_577 ? C11 H11 0.9300 . ? 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 O1 C8 119.34(16) . . ? C7 N1 H1 119.4(17) . . ? C7 N1 H2 119(2) . . ? H1 N1 H2 121(3) . . ? C6 C1 C2 118.41(17) . . ? C6 C1 C7 116.17(17) . . ? C2 C1 C7 125.41(17) . . ? O2 C7 N1 120.75(18) . . ? O2 C7 C1 118.62(18) . . ? N1 C7 C1 120.62(17) . . ? C4 C3 C2 120.46(18) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? O1 C2 C3 122.67(17) . . ? O1 C2 C1 117.38(17) . . ? C3 C2 C1 119.95(18) . . ? C5 C6 C1 121.44(18) . . ? C5 C6 H6 119.3 . . ? C1 C6 H6 119.3 . . ? C3 C4 C5 120.61(18) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 119.10(19) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? O1 C8 C9 106.60(17) . . ? O1 C8 H8A 110.4 . . ? C9 C8 H8A 110.4 . . ? O1 C8 H8B 110.4 . . ? C9 C8 H8B 110.4 . . ? H8A C8 H8B 108.6 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C10 O3 H3A 111.6(19) . . ? O4 C10 O3 124.90(18) . . ? O4 C10 C11 122.86(18) . . ? O3 C10 C11 112.24(16) . . ? C11 C11 C10 121.3(2) 2_577 . ? C11 C11 H11 119.4 2_577 . ? C10 C11 H11 119.4 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.479 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.071